#------------------------------------------------------------------------------ #$Date: 2022-08-09 04:26:26 +0200 (Tue, 09 Aug 2022) $ #$Revision: 277166 $ #$URL: svn://www.crystallography.net/cod/cif/2/02/26/2022651.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2022651 loop_ _publ_author_name 'Branowska, Danuta' 'Wysocki, Waldemar' 'Woli\'nska, Ewa' 'Koc, Karolina' 'Sta\'nska, Katarzyna' 'Miros\/law, Barbara' 'Karczmarzyk, Zbigniew' _publ_section_title ; Synthesis, structure and sulfonamide--sulfonimide tautomerism of sulfonamide--1,2,4-triazine derivatives ; _journal_coeditor_code EF3031 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C Structural Chemistry' _journal_paper_doi 10.1107/S2053229622007781 _journal_volume 78 _journal_year 2022 _chemical_formula_iupac 'C24 H20 N4 O4 S' _chemical_formula_moiety 'C24 H20 N4 O4 S' _chemical_formula_sum 'C24 H20 N4 O4 S' _chemical_formula_weight 460.50 _chemical_name_systematic ; Methyl 2-{[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfamoyl]methyl}benzoate ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _cell_angle_alpha 90 _cell_angle_beta 96.65(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.919(2) _cell_length_b 8.0871(16) _cell_length_c 24.875(5) _cell_measurement_reflns_used 3956 _cell_measurement_temperature 120.01(10) _cell_measurement_theta_max 75.5870 _cell_measurement_theta_min 4.6140 _cell_volume 2181.8(7) _computing_cell_refinement ; CrysAlis PRO (Agilent, 2014) ; _computing_data_collection ; CrysAlis PRO (Agilent, 2014) ; _computing_data_reduction ; CrysAlis PRO (Agilent, 2014) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) ; _computing_publication_material ; SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012) ; _computing_structure_refinement ; SHELXL2014 (Sheldrick, 2015) ; _computing_structure_solution ; SHELXS2013 (Sheldrick, 2008) ; _diffrn_ambient_temperature 120.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2763 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Agilent SuperNova Single Source diffractometer with an Atlas detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_unetI/netI 0.0626 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 8470 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 76.455 _diffrn_reflns_theta_min 3.578 _diffrn_source 'sealed X-ray tube' _exptl_absorpt_coefficient_mu 1.659 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.78171 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Agilent, 2014) ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.402 _exptl_crystal_description plate _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.637 _refine_diff_density_min -1.157 _refine_ls_extinction_coef 0.0015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method ; SHELXL2014 (Sheldrick, 2015) ; _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 302 _refine_ls_number_reflns 4438 _refine_ls_number_restraints 18 _refine_ls_restrained_S_all 1.184 _refine_ls_R_factor_all 0.0878 _refine_ls_R_factor_gt 0.0695 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1280P)^2^+2.0409P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2072 _refine_ls_wR_factor_ref 0.2526 _reflns_number_gt 3507 _reflns_number_total 4438 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file ef3031sup1.cif _cod_data_source_block 3b _cod_original_cell_volume 2181.9(8) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2022651 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_hkl_file ; 0 0 -2 514.60 11.50 0 0 -3 0.40 0.88 0 0 -4 0.35 0.72 0 0 -5 -0.26 0.78 0 0 -6 0.67 1.50 0 0 -7 -0.27 1.31 0 0 -8 11.21 4.44 0 0 -9 -0.23 1.30 0 0 -10 159.42 16.02 0 0 -11 2.14 2.21 0 0 -12 623.44 35.10 0 0 -13 1.33 2.54 0 0 -14 803.00 44.99 0 0 -15 0.82 2.28 0 0 15 150.68 19.47 0 0 -16 441.94 36.50 0 0 16 547.21 35.11 0 0 17 50.56 14.24 0 0 18 362.37 30.96 0 0 -19 1.96 2.14 0 0 19 5.75 5.62 0 0 -20 146.45 12.04 0 0 20 142.91 20.37 0 0 -21 -0.58 0.90 0 0 21 -10.13 5.69 0 0 -22 162.05 13.00 0 0 -23 0.31 1.05 0 0 -24 3.97 2.04 0 0 -25 -1.18 1.40 0 0 -26 1.75 1.39 0 0 -27 -0.68 1.08 0 0 -28 10.80 2.59 0 0 -29 1.00 0.94 0 0 -29 -0.04 0.28 0 0 -30 34.84 3.88 0 0 -31 0.52 0.39 0 1 0 0.32 0.18 0 1 0 -0.28 0.33 0 1 1 1556.70 21.28 0 1 1 1521.61 11.11 0 1 2 357.47 10.73 0 1 -2 321.79 11.26 0 -1 -3 907.56 19.79 0 1 -3 940.26 21.11 0 1 4 745.35 19.20 0 -1 -4 725.76 19.76 0 1 5 3749.59 47.42 0 -1 -5 3856.18 49.67 0 -1 -6 113.64 9.34 0 1 6 121.62 9.23 0 -1 -7 401.67 19.31 0 1 7 392.36 17.89 0 -1 -8 74.31 9.00 0 1 8 74.99 8.57 0 1 9 21.59 4.75 0 -1 -9 24.15 5.64 0 1 10 798.58 30.94 0 -1 -10 791.64 34.13 0 1 11 176.39 15.57 0 -1 -11 184.55 17.66 0 -1 -12 167.66 18.16 0 1 12 184.87 16.84 0 -1 -13 -0.77 2.80 0 1 13 2.78 2.85 0 1 14 0.89 1.43 0 -1 -14 2.11 2.99 0 1 15 108.33 14.73 0 -1 -15 120.16 17.91 0 1 16 202.34 20.99 0 -1 -16 185.70 23.33 0 -1 -17 143.25 21.73 0 1 17 139.82 18.30 0 1 18 208.55 23.48 0 -1 -18 171.19 24.94 0 -1 -19 34.46 5.81 0 1 -19 28.10 5.83 0 1 -19 32.89 5.72 0 1 19 32.03 8.25 0 -1 -19 32.10 11.62 0 1 -20 4.18 1.94 0 1 -20 4.80 2.25 0 -1 -20 4.02 2.37 0 1 20 1.00 3.87 0 1 21 0.76 2.95 0 1 -21 4.53 2.42 0 -1 -21 1.93 0.98 0 -1 -22 42.09 6.81 0 1 -22 44.21 6.61 0 -1 -23 36.92 6.22 0 1 -23 34.08 5.80 0 -1 -24 62.44 7.83 0 1 -24 67.67 8.02 0 -1 -25 65.42 7.72 0 1 -25 69.31 7.83 0 -1 -26 169.44 12.07 0 1 -26 173.12 11.96 0 -1 -27 31.11 4.67 0 1 -27 28.64 4.71 0 1 -28 23.77 3.92 0 -1 -28 24.05 4.01 0 1 -29 91.95 6.85 0 -1 -29 81.91 6.46 0 1 30 51.91 3.85 0 -1 -30 47.19 4.20 0 1 -30 47.88 4.44 0 1 -30 37.69 3.35 0 2 0 933.93 17.60 0 2 0 1005.05 24.95 0 2 1 9542.61 75.18 0 2 -1 9184.56 65.99 0 -2 -2 437.35 17.31 0 2 2 359.76 14.96 0 -2 -3 1095.77 27.76 0 -2 -4 1623.74 35.20 0 2 5 259.54 14.04 0 -2 -5 285.42 15.53 0 -2 -6 241.46 15.42 0 2 6 237.56 14.01 0 2 7 197.44 13.67 0 -2 -7 181.11 13.86 0 2 8 324.89 18.44 0 -2 -8 248.58 17.52 0 2 9 0.73 1.30 0 -2 -9 3.30 2.65 0 -2 -10 54.58 9.20 0 2 10 52.36 8.39 0 2 11 128.44 13.86 0 -2 -11 104.65 13.50 0 -2 -12 23.27 6.87 0 2 12 18.79 5.83 0 2 13 604.29 32.83 0 -2 -13 577.92 35.46 0 -2 -14 191.07 21.78 0 2 14 204.72 19.92 0 -2 -15 23.89 7.27 0 2 15 31.43 8.13 0 2 16 571.13 36.05 0 -2 -16 574.16 41.50 0 2 17 19.97 6.84 0 -2 -17 15.50 6.92 0 2 -18 -0.22 1.32 0 -2 -18 -2.56 2.91 0 2 -18 0.92 0.91 0 -2 -18 0.73 0.54 0 2 19 730.42 44.62 0 2 -19 753.25 26.96 0 -2 -19 728.19 26.29 0 2 -19 743.47 29.97 0 -2 -19 699.49 51.87 0 2 -20 112.30 11.99 0 2 -20 113.08 10.39 0 -2 -20 90.55 18.74 0 2 20 109.35 17.52 0 -2 -20 103.97 10.03 0 2 -21 -1.76 1.10 0 -2 -21 0.97 0.99 0 2 -21 -0.14 1.06 0 2 -22 123.39 10.86 0 -2 -22 137.17 11.55 0 2 -22 131.86 12.85 0 -2 -23 79.26 8.63 0 2 -23 86.51 8.97 0 -2 -24 36.75 6.02 0 2 -24 35.21 5.50 0 2 -25 3.46 1.96 0 -2 -25 1.76 1.12 0 2 -26 9.31 2.62 0 -2 -26 8.71 2.63 0 2 -27 24.13 3.91 0 -2 -27 19.00 3.65 0 2 -28 14.65 2.76 0 -2 -28 11.57 2.60 0 2 -29 40.46 4.20 0 2 29 49.11 4.43 0 2 -30 47.28 3.70 0 2 -30 61.03 4.12 0 2 30 56.67 3.87 0 3 0 0.91 1.42 0 3 1 2160.22 46.36 0 -3 -1 2608.52 50.76 0 -3 -2 -0.03 1.26 0 3 2 0.02 0.98 0 -3 -3 36.24 6.69 0 3 3 40.60 6.69 0 -3 -4 48.12 7.31 0 3 4 47.18 7.26 0 3 5 1144.92 35.78 0 -3 -5 1242.28 38.80 0 -3 -6 15.32 4.45 0 -3 -7 3.42 2.34 0 -3 -8 391.48 23.91 0 -3 -9 2645.85 64.56 0 -3 -10 413.69 27.05 0 3 11 317.33 22.98 0 -3 -11 276.52 23.33 0 -3 -12 351.80 27.88 0 3 12 366.61 25.77 0 -3 -13 61.57 12.36 0 3 13 58.67 10.42 0 -3 -14 13.89 6.14 0 3 14 11.12 4.82 0 -3 -15 394.84 33.72 0 3 15 393.62 29.77 0 3 16 7.23 4.38 0 -3 -16 6.96 4.65 0 3 -17 366.82 20.81 0 3 17 352.92 30.03 0 -3 -17 354.00 34.66 0 3 -18 192.65 15.47 0 3 18 210.20 23.71 0 -3 -18 197.40 13.21 0 3 -18 190.40 12.84 0 -3 -18 172.99 25.74 0 3 -19 5.24 2.13 0 -3 -19 5.56 2.00 0 3 -19 7.51 2.98 0 3 19 3.21 2.87 0 -3 -20 41.97 6.48 0 3 -20 47.34 6.52 0 3 -20 39.65 7.21 0 -3 -21 8.50 2.74 0 3 -21 4.29 1.81 0 3 -21 5.46 2.41 0 3 -22 43.65 7.60 0 -3 -22 40.49 5.92 0 3 -22 49.92 6.54 0 3 -23 7.11 2.56 0 3 -23 5.80 2.03 0 -3 -23 7.58 2.46 0 -3 -24 37.66 5.57 0 3 -24 31.97 4.90 0 -3 -25 75.76 7.31 0 3 -25 74.61 7.11 0 3 26 0.89 1.21 0 3 -26 -0.02 0.65 0 -3 -26 0.12 0.58 0 -3 -27 28.17 3.58 0 3 27 42.02 4.94 0 3 -28 0.41 0.44 0 3 28 0.35 0.63 0 3 29 19.15 2.55 0 -4 0 430.26 25.92 0 -4 -1 837.93 37.20 0 -4 -2 27.73 7.14 0 4 2 33.80 6.98 0 -4 -3 56.21 9.28 0 4 3 60.83 9.45 0 4 4 423.90 24.88 0 -4 -4 431.79 25.33 0 -4 -5 179.41 16.54 0 4 5 174.06 16.15 0 4 6 170.40 16.45 0 -4 -6 143.25 15.26 0 4 7 -0.82 1.88 0 -4 -7 0.69 1.41 0 -4 -8 35.55 8.46 0 4 8 51.16 9.48 0 4 9 77.10 12.10 0 -4 -9 59.34 10.99 0 -4 -10 237.98 22.87 0 4 10 255.85 22.57 0 -4 -11 167.82 20.28 0 4 11 213.82 21.22 0 4 12 119.69 16.32 0 -4 -12 101.87 15.94 0 4 13 297.69 26.55 0 -4 -13 299.27 29.03 0 -4 -14 146.53 21.23 0 4 -14 161.01 13.61 0 4 14 174.55 20.84 0 4 -15 1.55 2.06 0 4 -15 1.43 1.86 0 -4 -15 -0.03 1.70 0 4 -15 -0.87 1.08 0 -4 -16 11.50 7.08 0 4 -16 12.23 3.73 0 -4 -17 609.82 46.86 0 4 -17 641.62 28.20 0 4 -18 21.49 5.30 0 4 -19 194.45 15.84 0 4 -20 244.10 17.75 0 4 -21 2.48 1.68 0 4 22 2.75 2.25 0 4 -22 1.38 1.09 0 4 -23 94.07 10.30 0 4 23 123.31 10.24 0 4 24 71.27 7.43 0 4 25 1.22 1.21 0 4 26 10.21 2.48 0 4 27 11.28 2.29 0 4 28 -0.22 0.50 0 -5 0 0.05 1.24 0 -5 -1 118.94 15.81 0 -5 1 81.73 13.60 0 -5 -2 1484.15 55.03 0 -5 -3 46.37 9.91 0 -5 -4 3.47 1.98 0 5 4 2.20 1.34 0 -5 -5 2.49 2.61 0 5 5 7.85 4.78 0 -5 -6 158.80 18.97 0 5 6 160.84 18.45 0 5 7 78.89 13.21 0 -5 -7 65.30 12.65 0 -5 -8 40.56 10.02 0 5 8 34.35 8.88 0 5 9 28.82 8.13 0 -5 -9 23.56 8.39 0 -5 -10 257.91 26.48 0 5 10 298.25 26.83 0 5 11 8.53 2.74 0 -5 -11 12.26 6.48 0 5 -11 4.46 2.13 0 5 11 6.73 5.51 0 5 12 128.38 18.35 0 5 -12 146.81 12.91 0 5 12 123.33 10.38 0 -5 -12 134.96 20.34 0 5 13 10.78 6.26 0 -5 -13 4.38 4.75 0 5 -13 3.20 1.90 0 5 13 4.20 2.11 0 5 14 69.81 8.42 0 5 -14 76.72 9.90 0 -5 -14 67.30 15.39 0 5 -15 11.50 3.74 0 5 -15 12.40 4.18 0 5 15 10.53 3.36 0 5 -16 149.10 13.76 0 5 16 131.34 11.41 0 5 -17 3.34 2.75 0 5 17 2.40 2.17 0 5 -18 627.30 27.78 0 5 18 576.43 23.71 0 5 19 5.97 2.43 0 5 -19 3.94 2.60 0 5 20 49.45 6.74 0 5 -20 48.25 7.40 0 5 -21 17.36 4.28 0 5 21 13.25 3.52 0 5 -22 2.39 1.67 0 5 22 0.68 0.78 0 5 -23 0.89 0.94 0 5 23 0.50 1.31 0 5 24 185.80 10.63 0 5 25 23.24 3.37 0 5 26 0.37 0.56 0 -5 -27 0.49 0.67 0 5 27 0.18 0.33 0 -6 0 1503.84 63.85 0 -6 -1 67.22 13.84 0 -6 1 39.07 11.73 0 -6 -2 1.63 1.03 0 -6 2 -2.65 4.54 0 -6 3 8.09 5.80 0 -6 -3 16.61 7.47 0 -6 -4 31.98 9.77 0 -6 4 8.49 4.99 0 -6 -5 51.09 12.12 0 -6 -6 214.02 25.52 0 6 -6 222.29 13.08 0 6 -6 229.81 15.34 0 -6 -7 35.67 10.41 0 6 7 44.37 5.99 0 6 -7 34.26 6.09 0 6 -7 35.99 5.26 0 6 -8 270.79 17.27 0 6 8 277.21 27.62 0 -6 -8 256.46 27.72 0 6 8 240.30 14.09 0 -6 -9 62.72 14.04 0 6 -9 58.80 8.26 0 6 9 54.29 6.87 0 6 10 56.91 7.13 0 6 -10 66.50 8.91 0 -6 -10 60.77 14.44 0 6 -11 95.92 10.75 0 6 11 73.13 8.25 0 6 -12 139.77 13.08 0 6 12 120.73 10.66 0 6 13 12.34 3.59 0 6 -13 14.44 4.42 0 6 14 1.05 1.04 0 6 -14 0.49 1.67 0 6 -14 1.44 1.92 0 6 -15 30.17 6.00 0 6 15 29.19 5.38 0 6 -15 26.78 5.78 0 6 -16 30.26 6.14 0 6 16 25.25 4.70 0 6 17 -0.18 0.77 0 6 -17 -0.92 1.65 0 6 -18 6.38 2.80 0 6 18 7.01 2.41 0 6 -19 0.84 1.47 0 6 19 1.73 1.41 0 6 -20 2.27 1.60 0 6 20 0.28 1.14 0 6 -21 119.67 10.05 0 6 21 110.55 8.55 0 6 -22 28.54 4.57 0 6 22 20.79 3.45 0 6 23 10.46 2.29 0 -6 -24 53.66 5.22 0 -6 -25 1.08 0.74 0 7 0 1.59 1.84 0 7 1 201.18 14.18 0 7 -1 190.98 13.58 0 7 -2 234.82 14.89 0 7 2 256.58 16.07 0 7 -3 32.75 5.52 0 7 -4 20.15 4.63 0 7 -4 20.16 4.27 0 7 -5 2.76 1.79 0 7 -5 0.67 0.52 0 7 -6 36.86 6.56 0 7 -6 32.88 5.28 0 7 -7 22.49 5.16 0 7 -7 20.92 4.19 0 7 -8 0.25 0.85 0 7 -8 -0.23 0.77 0 7 -9 1.12 1.19 0 7 -10 39.97 6.77 0 7 10 39.06 6.01 0 -7 -11 2.30 1.77 0 7 11 0.78 1.04 0 7 -11 0.61 0.99 0 7 -12 73.51 8.98 0 -7 -12 73.73 8.53 0 7 12 81.05 8.25 0 7 -12 82.63 9.75 0 7 13 119.73 9.59 0 7 -13 119.99 11.25 0 -7 -13 113.81 10.65 0 7 -13 116.82 11.39 0 7 -14 50.99 7.26 0 7 14 49.74 5.86 0 -7 -14 44.54 6.55 0 -7 -15 2.35 1.33 0 7 -15 4.76 2.33 0 7 -16 3.25 1.55 0 -7 -16 3.85 2.05 0 -7 -17 42.99 5.99 0 7 -17 39.99 5.87 0 7 -18 176.51 11.75 0 -7 -18 196.41 12.19 0 -7 -19 0.45 0.51 0 7 -19 0.29 0.82 0 7 -20 22.55 3.69 0 -7 -20 22.93 3.63 0 -7 -21 -0.15 0.42 0 -7 -22 31.64 3.30 0 8 0 9.51 3.17 0 8 1 257.92 15.64 0 8 -1 250.41 15.12 0 8 -2 1.43 1.66 0 8 2 1.56 1.63 0 8 3 43.05 6.45 0 8 -3 40.79 5.97 0 8 4 52.19 6.95 0 8 -4 46.67 6.20 0 8 5 5.15 1.70 0 8 -5 3.90 1.59 0 8 -5 5.93 2.53 0 8 -6 77.91 7.57 0 8 6 73.08 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3.05 -12 -1 11 1.18 0.87 -12 1 11 0.35 1.62 12 1 -10 1.80 1.05 -12 -1 10 2.06 1.86 -12 1 10 1.42 1.10 12 1 -9 0.31 0.77 -12 -1 9 0.11 2.03 -12 1 9 -0.59 0.72 12 1 -8 37.21 4.79 -12 -1 8 31.97 6.21 12 1 -7 8.37 2.67 -12 -1 7 5.43 4.31 -12 1 7 5.50 2.94 -12 -1 6 91.08 10.08 -12 1 6 4.72 3.55 -12 -1 5 1.27 2.14 -12 1 5 -0.38 0.89 -12 -1 4 33.16 6.38 -12 1 4 5.23 3.72 -12 -1 3 1.98 1.73 -12 1 3 1.47 1.45 -12 -1 2 36.28 6.24 -12 1 2 47.08 6.07 -12 -1 1 2.94 2.18 -12 1 1 1.14 1.10 -12 -1 0 11.76 3.89 -12 1 0 16.33 4.40 -12 -1 -1 4.95 2.95 -12 1 -1 12.82 3.15 -12 -1 -2 0.39 0.78 -12 1 -2 1.69 1.80 -12 -1 -3 18.53 4.61 -12 1 -3 38.00 5.55 -12 -1 -4 27.77 5.26 -12 1 -4 52.93 6.36 -12 -1 -5 7.95 2.57 -12 1 -5 9.27 2.63 -12 -1 -6 25.23 4.03 -12 1 -6 29.47 4.37 -12 -1 -7 2.02 1.22 -12 1 -7 1.64 1.51 -12 -1 -8 2.51 1.25 -12 1 -8 -0.80 0.90 -12 -1 -9 35.75 3.74 -12 1 -9 36.54 4.35 -12 -1 -10 55.79 4.42 -12 1 -10 65.16 5.46 -12 1 -11 19.01 2.63 12 2 -17 0.99 0.67 12 2 -16 0.30 0.32 12 2 -15 9.69 1.73 12 2 -14 23.08 2.93 12 2 -13 44.98 4.30 -12 -2 13 23.48 6.11 12 2 -12 -0.75 0.61 -12 -2 12 2.32 2.18 -12 2 12 0.03 1.24 12 2 -11 7.27 1.96 -12 -2 11 6.14 3.95 -12 2 11 -0.04 0.97 12 2 -10 1.78 1.02 -12 -2 10 2.99 2.40 -12 2 10 0.95 1.29 -12 -2 9 14.49 4.40 -12 2 9 6.29 2.62 12 2 -8 0.94 0.95 -12 -2 8 -1.00 1.56 -12 2 8 -0.59 0.87 12 2 -7 1.30 1.41 -12 -2 7 -1.07 1.31 -12 2 7 0.29 1.17 -12 -2 6 9.76 4.69 -12 2 6 2.54 2.76 -12 -2 5 43.82 8.50 -12 2 5 9.30 4.62 -12 -2 4 9.47 4.40 -12 2 4 4.22 2.32 -12 -2 3 2.19 2.87 -12 2 3 1.95 1.85 -12 -2 2 5.53 2.38 -12 2 2 2.45 1.73 -12 -2 1 19.09 4.64 -12 2 1 17.82 3.72 -12 -2 0 4.56 1.85 -12 2 0 5.49 2.48 -12 -2 -1 2.46 1.48 -12 2 -1 4.08 1.94 -12 -2 -2 1.60 1.25 -12 2 -2 3.62 1.81 -12 -2 -3 93.39 8.81 -12 2 -3 171.26 10.76 -12 -2 -4 -0.93 1.44 -12 2 -4 2.35 1.53 -12 -2 -5 3.61 1.53 -12 2 -5 10.75 2.58 -12 -2 -6 15.09 2.66 -12 2 -6 16.97 3.29 -12 2 -7 1.11 1.01 -12 2 -8 1.06 0.76 -12 2 -9 3.38 1.39 -12 2 -10 1.36 0.89 12 3 -15 1.52 0.64 12 3 -14 0.48 0.28 12 3 -13 2.35 1.12 12 3 -12 23.84 3.11 12 3 -11 2.88 1.28 -12 -3 11 0.55 1.34 12 3 -10 1.78 0.98 -12 -3 10 1.22 1.94 12 3 -9 25.84 3.56 -12 -3 9 21.57 4.49 12 3 -8 0.74 0.96 -12 -3 8 0.38 0.98 12 3 -7 56.82 5.37 -12 -3 7 46.15 6.71 12 3 -6 0.53 1.39 -12 -3 6 3.09 1.67 12 3 -5 11.39 2.68 -12 -3 5 10.21 2.80 -12 -3 4 2.04 1.37 -12 3 4 0.02 0.62 -12 -3 3 0.73 0.84 -12 3 3 -0.34 0.74 -12 -3 2 3.80 2.09 -12 3 2 1.14 0.77 -12 -3 1 29.12 4.95 -12 3 1 20.02 3.62 -12 -3 0 16.80 3.49 -12 3 0 9.58 2.61 -12 3 -1 78.39 6.61 -12 3 -2 0.27 0.46 -12 3 -3 40.68 4.55 -12 3 -4 0.68 1.01 -12 3 -5 54.43 5.09 -12 3 -6 3.64 1.27 -12 3 -7 38.03 3.80 -12 3 -8 8.90 1.75 12 4 -12 29.49 2.94 12 4 -11 -0.17 0.41 12 4 -10 24.06 2.90 12 4 -9 4.30 1.20 12 4 -8 30.68 3.40 12 4 -7 8.07 1.82 12 4 -6 20.89 2.94 12 4 -5 41.72 4.15 12 4 -4 1.02 1.02 12 4 -3 16.19 2.73 12 4 -2 3.36 1.83 -13 0 12 -0.02 0.69 -13 0 11 0.33 1.00 -13 0 10 0.20 0.62 -13 0 9 0.56 1.44 -13 0 8 1.59 2.24 -13 0 7 8.17 2.81 -13 0 6 -0.29 0.62 -13 0 5 -0.29 0.74 -13 0 4 0.15 1.30 -13 0 3 1.86 1.55 -13 0 2 -0.25 0.83 -13 0 1 0.05 0.53 -13 0 0 0.04 1.10 -13 0 -1 8.39 2.87 -13 0 -2 0.51 0.52 -13 0 -3 3.25 1.50 -13 0 -4 0.59 0.76 -13 0 -5 0.38 0.72 -13 0 -6 -1.16 0.81 -13 -1 12 -0.84 0.90 -13 -1 11 1.39 1.36 -13 1 11 -0.53 0.60 -13 -1 10 2.53 1.98 -13 1 10 1.62 1.56 -13 -1 9 18.78 4.76 -13 1 9 2.55 1.91 -13 -1 8 5.32 2.34 -13 1 8 2.33 1.96 13 1 -7 -0.03 0.62 -13 -1 7 0.55 0.92 -13 1 7 -1.77 1.25 13 1 -6 -0.54 0.55 -13 -1 6 -0.11 1.01 -13 1 6 -1.81 1.24 13 1 -5 2.59 1.10 -13 -1 5 -0.51 0.75 -13 1 5 1.48 1.77 -13 -1 4 1.95 2.39 -13 1 4 0.40 1.34 -13 -1 3 0.86 1.65 -13 1 3 1.27 1.50 -13 -1 2 1.35 1.36 -13 1 2 -0.39 0.72 -13 -1 1 4.51 2.12 -13 1 1 0.59 0.91 -13 -1 0 -1.82 1.14 -13 1 0 -0.33 0.59 -13 -1 -1 -0.65 0.68 -13 1 -1 -0.02 1.00 -13 -1 -2 0.85 0.88 -13 1 -2 0.89 1.23 -13 -1 -3 -0.67 0.51 -13 1 -3 -0.04 0.61 -13 -1 -4 3.16 1.53 -13 1 -4 2.17 1.19 -13 -1 -5 0.77 0.66 -13 1 -5 0.71 1.04 -13 1 -6 0.64 0.60 -13 -2 10 5.02 2.21 13 2 -9 0.26 0.48 -13 -2 9 4.47 2.06 -13 -2 8 12.86 3.32 -13 2 8 0.04 0.38 -13 -2 7 4.94 2.24 -13 2 7 -0.50 0.75 13 2 -6 1.07 1.12 -13 -2 6 -0.93 1.00 -13 2 6 2.21 1.61 -13 -2 5 4.49 1.85 -13 2 5 0.96 1.19 -13 -2 4 0.08 0.95 -13 2 4 0.89 1.30 13 2 -3 3.97 1.76 -13 -2 3 2.92 1.95 -13 2 3 1.90 1.08 -13 -2 2 8.27 2.73 -13 2 2 1.37 1.23 -13 -2 1 2.08 1.52 -13 2 1 1.05 1.26 -13 -2 0 6.71 2.04 -13 2 0 0.45 0.85 -13 -2 -1 1.77 1.06 -13 2 -1 -0.66 0.46 -13 2 -2 0.35 0.70 -13 2 -3 5.07 1.44 -13 2 -4 1.95 1.08 13 3 -7 2.81 1.00 13 3 -6 58.76 3.99 13 3 -5 2.66 0.95 13 3 -4 4.97 1.21 13 3 -3 0.90 0.53 13 3 -2 8.74 1.65 13 3 -1 3.85 1.08 13 3 0 16.61 2.20 13 3 1 10.43 1.76 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 10419 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL 35 in P2(1)/n CELL 1.54178 10.9195 8.0871 24.8751 90.000 96.648 90.000 ZERR 4.00 0.0022 0.0016 0.0050 0.000 0.030 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 96 80 16 16 4 MERG 2 FMAP 2 PLAN 20 SIMU 0.001 N7 C3 N4 C5 ACTA BOND $H CONF L.S. 60 WGHT 0.128000 2.040900 EXTI 0.001478 FVAR 0.51269 C3 1 0.585615 0.339682 0.631608 11.00000 0.03257 0.03141 = 0.02310 0.00048 0.00672 0.00249 C5 1 0.578496 0.361247 0.722132 11.00000 0.03431 0.02564 = 0.02372 0.00013 0.00609 0.00079 C6 1 0.709434 0.348185 0.729066 11.00000 0.03543 0.01963 = 0.02785 0.00017 0.01168 -0.00045 C9 1 0.327130 0.523078 0.592423 11.00000 0.03467 0.03215 = 0.02682 -0.00029 0.00218 -0.00302 AFIX 23 H9A 2 0.349146 0.517707 0.631296 11.00000 -1.50000 H9B 2 0.369944 0.616668 0.578904 11.00000 -1.50000 AFIX 0 C10 1 0.211138 0.763772 0.507756 11.00000 0.03989 0.03054 = 0.02569 -0.00247 0.00795 0.00449 C12 1 0.213950 0.989106 0.449133 11.00000 0.06520 0.02889 = 0.03867 0.00371 0.01268 0.00125 AFIX 33 H12A 2 0.159887 1.071894 0.431918 11.00000 -1.50000 H12B 2 0.279958 1.041666 0.471699 11.00000 -1.50000 H12C 2 0.247313 0.923950 0.422034 11.00000 -1.50000 AFIX 0 C51 1 0.498733 0.384926 0.765959 11.00000 0.03171 0.02647 = 0.02542 0.00114 0.00839 0.00377 C52 1 0.384482 0.303272 0.761238 11.00000 0.03796 0.03683 = 0.03335 -0.00218 0.00796 -0.00249 AFIX 43 H52 2 0.362305 0.232846 0.732182 11.00000 -1.50000 AFIX 0 C53 1 0.304919 0.328015 0.800028 11.00000 0.04123 0.04977 = 0.04346 -0.00230 0.02260 -0.00175 AFIX 43 H53 2 0.230597 0.270834 0.797683 11.00000 -1.50000 AFIX 0 C54 1 0.335519 0.437494 0.842283 11.00000 0.04548 0.05334 = 0.03502 0.00438 0.01651 0.01184 AFIX 43 H54 2 0.281045 0.455374 0.867796 11.00000 -1.50000 AFIX 0 C55 1 0.446763 0.519970 0.846515 11.00000 0.05141 0.04004 = 0.03236 -0.00679 0.00975 0.01227 AFIX 43 H55 2 0.467222 0.592920 0.875046 11.00000 -1.50000 AFIX 0 C56 1 0.528439 0.494805 0.808453 11.00000 0.04143 0.03052 = 0.03302 -0.00298 0.00789 0.00144 AFIX 43 H56 2 0.603025 0.551473 0.811393 11.00000 -1.50000 AFIX 0 C61 1 0.790239 0.347080 0.781002 11.00000 0.03159 0.02136 = 0.02850 -0.00233 0.00676 0.00251 C62 1 0.763474 0.254548 0.825794 11.00000 0.03415 0.02720 = 0.02688 -0.00016 0.00358 0.00235 AFIX 43 H62 2 0.691780 0.191645 0.823687 11.00000 -1.50000 AFIX 0 C63 1 0.844106 0.256594 0.873507 11.00000 0.04871 0.03297 = 0.02585 0.00003 0.00424 0.00699 AFIX 43 H63 2 0.826634 0.193335 0.902898 11.00000 -1.50000 AFIX 0 C64 1 0.950180 0.352211 0.877503 11.00000 0.03988 0.03470 = 0.03340 -0.00671 -0.00407 0.00829 AFIX 43 H64 2 1.002537 0.355433 0.909753 11.00000 -1.50000 AFIX 0 C65 1 0.977772 0.442886 0.833235 11.00000 0.03387 0.03178 = 0.04055 -0.00207 -0.00417 0.00186 AFIX 43 H65 2 1.048704 0.507424 0.835832 11.00000 -1.50000 AFIX 0 C66 1 0.900251 0.437841 0.785175 11.00000 0.03575 0.02724 = 0.03587 0.00148 0.00578 0.00331 AFIX 43 H66 2 0.921416 0.495442 0.755236 11.00000 -1.50000 AFIX 0 C91 1 0.190937 0.549573 0.580611 11.00000 0.03189 0.03027 = 0.02700 -0.00463 0.01014 0.00164 C92 1 0.135800 0.660986 0.542037 11.00000 0.03441 0.02926 = 0.03198 -0.00481 0.01347 0.00183 C93 1 0.007616 0.679496 0.534764 11.00000 0.03906 0.03520 = 0.04327 -0.00423 0.01095 0.00823 AFIX 43 H93 2 -0.028888 0.753714 0.509197 11.00000 -1.50000 AFIX 0 C94 1 -0.064820 0.587172 0.565680 11.00000 0.03678 0.04172 = 0.05469 -0.00871 0.01683 0.00066 AFIX 43 H94 2 -0.150096 0.598889 0.560478 11.00000 -1.50000 AFIX 0 C95 1 -0.011686 0.477783 0.604192 11.00000 0.03589 0.03801 = 0.04760 -0.00381 0.02043 -0.00180 AFIX 43 H95 2 -0.060767 0.416177 0.624907 11.00000 -1.50000 AFIX 0 C96 1 0.115059 0.460737 0.611656 11.00000 0.04618 0.03192 = 0.03664 0.00129 0.01646 0.00126 AFIX 43 H96 2 0.150653 0.388303 0.638008 11.00000 -1.50000 AFIX 0 N1 3 0.769008 0.334216 0.685408 11.00000 0.03376 0.02968 = 0.02460 0.00056 0.00278 0.00191 N2 3 0.709166 0.332564 0.635647 11.00000 0.03366 0.03288 = 0.02788 -0.00165 0.00770 0.00243 N4 3 0.518659 0.353379 0.672748 11.00000 0.03327 0.02846 = 0.02284 0.00042 0.00512 0.00180 N7 3 0.525823 0.338823 0.579549 11.00000 0.03273 0.03573 = 0.02194 0.00066 0.00455 0.00327 H7 2 0.573598 0.320455 0.552897 11.00000 -1.50000 O1 4 0.323550 0.199688 0.586551 11.00000 0.04021 0.03162 = 0.03909 0.00106 0.00425 0.00231 O2 4 0.362595 0.352141 0.504555 11.00000 0.04528 0.04700 = 0.02309 -0.00334 0.00270 0.00572 O10 4 0.319611 0.742101 0.503630 11.00000 0.03522 0.04756 = 0.03536 0.00925 0.01437 0.00663 O11 4 0.145597 0.883210 0.481942 11.00000 0.04895 0.03186 = 0.04450 0.00826 0.01095 0.00808 S8 5 0.376577 0.338079 0.562390 11.00000 0.03475 0.03199 = 0.02477 -0.00209 0.00630 0.00156 HKLF 4 REM 35 in P2(1)/n REM R1 = 0.0695 for 3507 Fo > 4sig(Fo) and 0.0878 for all 4438 data REM 302 parameters refined using 18 restraints END WGHT 0.1275 2.0442 REM Highest difference peak 0.637, deepest hole -1.157, 1-sigma level 0.098 Q1 1 0.2652 0.3371 0.5763 11.00000 0.05 0.64 Q2 1 0.4841 0.2885 0.5565 11.00000 0.05 0.55 Q3 1 0.2599 0.3357 0.5320 11.00000 0.05 0.44 Q4 1 0.9611 0.3625 0.8472 11.00000 0.05 0.43 Q5 1 0.1750 0.3103 0.5704 11.00000 0.05 0.43 Q6 1 0.4835 0.3983 0.5576 11.00000 0.05 0.42 Q7 1 0.4016 0.2944 0.5216 11.00000 0.05 0.41 Q8 1 0.3532 0.4145 0.5761 11.00000 0.05 0.40 Q9 1 0.5646 0.3986 0.5531 11.00000 0.05 0.39 Q10 1 0.5787 0.3433 0.6145 11.00000 0.05 0.38 Q11 1 -0.1752 0.6639 0.4864 11.00000 0.05 0.38 Q12 1 0.3478 0.3623 0.5996 11.00000 0.05 0.36 Q13 1 0.4789 0.3357 0.4959 11.00000 0.05 0.36 Q14 1 0.5405 0.3216 0.6668 11.00000 0.05 0.35 Q15 1 0.4761 0.3223 0.6428 11.00000 0.05 0.34 Q16 1 0.4155 0.3542 0.6161 11.00000 0.05 0.33 Q17 1 0.8840 0.3004 0.6766 11.00000 0.05 0.33 Q18 1 0.9948 0.3545 0.9342 11.00000 0.05 0.33 Q19 1 0.2009 0.7038 0.4318 11.00000 0.05 0.32 Q20 1 0.6831 0.3087 0.7119 11.00000 0.05 0.31 ; _shelx_res_checksum 94413 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C3 0.5856(3) 0.3397(4) 0.63161(13) 0.0288(5) Uani d 1 . . C C5 0.5785(3) 0.3612(4) 0.72213(13) 0.0277(5) Uani d 1 . . C C6 0.7094(3) 0.3482(4) 0.72907(14) 0.0270(7) Uani d 1 . . C C9 0.3271(3) 0.5231(5) 0.59242(14) 0.0313(7) Uani d 1 . . H H9A 0.3491 0.5177 0.6313 0.047 Uiso calc 1 . . H H9B 0.3699 0.6167 0.5789 0.047 Uiso calc 1 . . C C10 0.2111(3) 0.7638(4) 0.50776(13) 0.0317(7) Uani d 1 . . C C12 0.2140(4) 0.9891(5) 0.44913(17) 0.0437(10) Uani d 1 . . H H12A 0.1599 1.0719 0.4319 0.066 Uiso calc 1 . . H H12B 0.2800 1.0417 0.4717 0.066 Uiso calc 1 . . H H12C 0.2473 0.9239 0.4220 0.066 Uiso calc 1 . . C C51 0.4987(3) 0.3849(4) 0.76596(13) 0.0275(7) Uani d 1 . . C C52 0.3845(4) 0.3033(5) 0.76124(15) 0.0357(8) Uani d 1 . . H H52 0.3623 0.2328 0.7322 0.054 Uiso calc 1 . . C C53 0.3049(4) 0.3280(6) 0.80003(17) 0.0434(10) Uani d 1 . . H H53 0.2306 0.2708 0.7977 0.065 Uiso calc 1 . . C C54 0.3355(4) 0.4375(6) 0.84228(16) 0.0437(10) Uani d 1 . . H H54 0.2810 0.4554 0.8678 0.066 Uiso calc 1 . . C C55 0.4468(4) 0.5200(5) 0.84652(15) 0.0409(9) Uani d 1 . . H H55 0.4672 0.5929 0.8750 0.061 Uiso calc 1 . . C C56 0.5284(4) 0.4948(5) 0.80845(15) 0.0347(8) Uani d 1 . . H H56 0.6030 0.5515 0.8114 0.052 Uiso calc 1 . . C C61 0.7902(3) 0.3471(4) 0.78100(14) 0.0269(7) Uani d 1 . . C C62 0.7635(3) 0.2545(4) 0.82579(13) 0.0294(7) Uani d 1 . . H H62 0.6918 0.1916 0.8237 0.044 Uiso calc 1 . . C C63 0.8441(4) 0.2566(5) 0.87351(14) 0.0358(8) Uani d 1 . . H H63 0.8266 0.1933 0.9029 0.054 Uiso calc 1 . . C C64 0.9502(4) 0.3522(5) 0.87750(16) 0.0366(8) Uani d 1 . . H H64 1.0025 0.3554 0.9098 0.055 Uiso calc 1 . . C C65 0.9778(3) 0.4429(5) 0.83323(16) 0.0361(8) Uani d 1 . . H H65 1.0487 0.5074 0.8358 0.054 Uiso calc 1 . . C C66 0.9003(3) 0.4378(4) 0.78517(15) 0.0328(7) Uani d 1 . . H H66 0.9214 0.4954 0.7552 0.049 Uiso calc 1 . . C C91 0.1909(3) 0.5496(4) 0.58061(13) 0.0292(7) Uani d 1 . . C C92 0.1358(3) 0.6610(4) 0.54204(14) 0.0311(7) Uani d 1 . . C C93 0.0076(4) 0.6795(5) 0.53476(17) 0.0387(9) Uani d 1 . . H H93 -0.0289 0.7537 0.5092 0.058 Uiso calc 1 . . C C94 -0.0648(4) 0.5872(5) 0.56568(18) 0.0435(9) Uani d 1 . . H H94 -0.1501 0.5989 0.5605 0.065 Uiso calc 1 . . C C95 -0.0117(4) 0.4778(5) 0.60419(17) 0.0393(9) Uani d 1 . . H H95 -0.0608 0.4162 0.6249 0.059 Uiso calc 1 . . C C96 0.1151(4) 0.4607(5) 0.61166(15) 0.0373(8) Uani d 1 . . H H96 0.1507 0.3883 0.6380 0.056 Uiso calc 1 . . N N1 0.7690(3) 0.3342(4) 0.68541(12) 0.0294(6) Uani d 1 . . N N2 0.7092(3) 0.3326(4) 0.63565(12) 0.0312(7) Uani d 1 . . N N4 0.5187(3) 0.3534(4) 0.67275(11) 0.0280(5) Uani d 1 . . N N7 0.5258(3) 0.3388(4) 0.57955(11) 0.0300(5) Uani d 1 . . H H7 0.574(4) 0.320(6) 0.553(2) 0.045 Uiso d 1 . . O O1 0.3236(2) 0.1997(3) 0.58655(11) 0.0370(6) Uani d 1 . . O O2 0.3626(3) 0.3521(4) 0.50456(10) 0.0386(7) Uani d 1 . . O O10 0.3196(2) 0.7421(4) 0.50363(11) 0.0386(6) Uani d 1 . . O O11 0.1456(3) 0.8832(3) 0.48194(12) 0.0413(7) Uani d 1 . . S S8 0.37658(8) 0.33808(11) 0.56239(3) 0.0303(3) Uani d 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C3 0.0326(10) 0.0314(10) 0.0231(10) 0.0025(8) 0.0067(9) 0.0005(8) C5 0.0343(11) 0.0256(11) 0.0237(11) 0.0008(9) 0.0061(10) 0.0001(9) C6 0.0354(17) 0.0196(14) 0.0279(16) -0.0004(12) 0.0117(13) 0.0002(11) C9 0.0347(17) 0.0321(17) 0.0268(15) -0.0030(14) 0.0022(13) -0.0003(13) C10 0.0399(18) 0.0305(17) 0.0257(15) 0.0045(15) 0.0079(13) -0.0025(13) C12 0.065(3) 0.0289(18) 0.039(2) 0.0013(18) 0.0127(18) 0.0037(16) C51 0.0317(16) 0.0265(15) 0.0254(15) 0.0038(13) 0.0084(12) 0.0011(12) C52 0.0380(19) 0.0368(18) 0.0333(17) -0.0025(16) 0.0080(15) -0.0022(15) C53 0.041(2) 0.050(2) 0.043(2) -0.0018(18) 0.0226(18) -0.0023(17) C54 0.045(2) 0.053(2) 0.0350(19) 0.0118(19) 0.0165(16) 0.0044(17) C55 0.051(2) 0.040(2) 0.0324(18) 0.0123(18) 0.0098(16) -0.0068(15) C56 0.0414(19) 0.0305(17) 0.0330(17) 0.0014(15) 0.0079(15) -0.0030(14) C61 0.0316(17) 0.0214(15) 0.0285(16) 0.0025(12) 0.0068(13) -0.0023(12) C62 0.0341(17) 0.0272(16) 0.0269(15) 0.0023(14) 0.0036(13) -0.0002(12) C63 0.049(2) 0.0330(18) 0.0258(16) 0.0070(16) 0.0042(15) 0.0000(13) C64 0.0399(19) 0.0347(19) 0.0334(18) 0.0083(16) -0.0041(15) -0.0067(14) C65 0.0339(18) 0.0318(18) 0.0405(19) 0.0019(15) -0.0042(15) -0.0021(15) C66 0.0357(18) 0.0272(16) 0.0359(17) 0.0033(14) 0.0058(14) 0.0015(14) C91 0.0319(16) 0.0303(16) 0.0270(15) 0.0016(14) 0.0101(13) -0.0046(13) C92 0.0344(18) 0.0293(17) 0.0320(17) 0.0018(14) 0.0135(14) -0.0048(13) C93 0.039(2) 0.0352(19) 0.043(2) 0.0082(16) 0.0110(16) -0.0042(16) C94 0.0368(19) 0.042(2) 0.055(2) 0.0007(17) 0.0168(17) -0.0087(18) C95 0.0359(19) 0.0380(19) 0.048(2) -0.0018(16) 0.0204(16) -0.0038(17) C96 0.046(2) 0.0319(18) 0.0366(18) 0.0013(16) 0.0165(16) 0.0013(15) N1 0.0338(15) 0.0297(14) 0.0246(13) 0.0019(11) 0.0028(11) 0.0006(11) N2 0.0337(15) 0.0329(15) 0.0279(14) 0.0024(12) 0.0077(12) -0.0017(11) N4 0.0333(10) 0.0285(10) 0.0228(9) 0.0018(8) 0.0051(8) 0.0004(7) N7 0.0327(11) 0.0357(11) 0.0219(10) 0.0033(9) 0.0045(9) 0.0007(9) O1 0.0402(14) 0.0316(13) 0.0391(14) 0.0023(11) 0.0042(11) 0.0011(11) O2 0.0453(15) 0.0470(16) 0.0231(12) 0.0057(12) 0.0027(11) -0.0033(10) O10 0.0352(13) 0.0476(16) 0.0354(13) 0.0066(12) 0.0144(11) 0.0093(12) O11 0.0489(16) 0.0319(13) 0.0445(15) 0.0081(12) 0.0109(12) 0.0083(12) S8 0.0347(5) 0.0320(5) 0.0248(4) 0.0016(3) 0.0063(3) -0.0021(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N4 C3 N2 . . 125.7(3) ? N4 C3 N7 . . 118.7(3) ? N2 C3 N7 . . 115.6(3) ? N4 C5 C6 . . 119.3(3) ? N4 C5 C51 . . 114.8(3) ? C6 C5 C51 . . 125.9(3) ? N1 C6 C5 . . 119.0(3) ? N1 C6 C61 . . 114.4(3) ? C5 C6 C61 . . 126.6(3) ? C91 C9 S8 . . 112.3(2) ? C91 C9 H9A . . 109.1 ? S8 C9 H9A . . 109.1 ? C91 C9 H9B . . 109.1 ? S8 C9 H9B . . 109.1 ? H9A C9 H9B . . 107.9 ? O10 C10 O11 . . 122.9(3) ? O10 C10 C92 . . 124.9(3) ? O11 C10 C92 . . 112.2(3) ? O11 C12 H12A . . 109.5 ? O11 C12 H12B . . 109.5 ? H12A C12 H12B . . 109.5 ? O11 C12 H12C . . 109.5 ? H12A C12 H12C . . 109.5 ? H12B C12 H12C . . 109.5 ? C56 C51 C52 . . 119.4(3) ? C56 C51 C5 . . 122.4(3) ? C52 C51 C5 . . 118.0(3) ? C53 C52 C51 . . 119.8(4) ? C53 C52 H52 . . 120.1 ? C51 C52 H52 . . 120.1 ? C54 C53 C52 . . 120.3(4) ? C54 C53 H53 . . 119.8 ? C52 C53 H53 . . 119.8 ? C55 C54 C53 . . 120.0(3) ? C55 C54 H54 . . 120.0 ? C53 C54 H54 . . 120.0 ? C54 C55 C56 . . 120.4(4) ? C54 C55 H55 . . 119.8 ? C56 C55 H55 . . 119.8 ? C55 C56 C51 . . 120.0(4) ? C55 C56 H56 . . 120.0 ? C51 C56 H56 . . 120.0 ? C62 C61 C66 . . 118.5(3) ? C62 C61 C6 . . 122.7(3) ? C66 C61 C6 . . 118.8(3) ? C63 C62 C61 . . 120.1(3) ? C63 C62 H62 . . 119.9 ? C61 C62 H62 . . 119.9 ? C64 C63 C62 . . 120.5(3) ? C64 C63 H63 . . 119.7 ? C62 C63 H63 . . 119.7 ? C65 C64 C63 . . 119.7(4) ? C65 C64 H64 . . 120.2 ? C63 C64 H64 . . 120.2 ? C66 C65 C64 . . 120.3(4) ? C66 C65 H65 . . 119.9 ? C64 C65 H65 . . 119.9 ? C65 C66 C61 . . 120.9(3) ? C65 C66 H66 . . 119.6 ? C61 C66 H66 . . 119.6 ? C96 C91 C92 . . 118.3(3) ? C96 C91 C9 . . 117.2(3) ? C92 C91 C9 . . 124.4(3) ? C93 C92 C91 . . 120.1(3) ? C93 C92 C10 . . 118.2(3) ? C91 C92 C10 . . 121.6(3) ? C94 C93 C92 . . 119.9(4) ? C94 C93 H93 . . 120.1 ? C92 C93 H93 . . 120.1 ? C95 C94 C93 . . 120.6(4) ? C95 C94 H94 . . 119.7 ? C93 C94 H94 . . 119.7 ? C94 C95 C96 . . 119.4(4) ? C94 C95 H95 . . 120.3 ? C96 C95 H95 . . 120.3 ? C95 C96 C91 . . 121.6(4) ? C95 C96 H96 . . 119.2 ? C91 C96 H96 . . 119.2 ? N2 N1 C6 . . 121.7(3) ? N1 N2 C3 . . 116.7(3) ? C5 N4 C3 . . 117.5(3) ? C3 N7 S8 . . 126.4(3) ? C3 N7 H7 . . 116(3) ? S8 N7 H7 . . 117(3) ? C10 O11 C12 . . 114.8(3) ? O1 S8 O2 . . 118.97(18) ? O1 S8 N7 . . 109.51(16) ? O2 S8 N7 . . 104.40(16) ? O1 S8 C9 . . 108.95(17) ? O2 S8 C9 . . 110.58(17) ? N7 S8 C9 . . 103.20(16) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C3 N4 . 1.329(4) ? C3 N2 . 1.342(5) ? C3 N7 . 1.381(4) ? C5 N4 . 1.324(4) ? C5 C6 . 1.424(5) ? C5 C51 . 1.484(4) ? C6 N1 . 1.334(4) ? C6 C61 . 1.478(5) ? C9 C91 . 1.498(5) ? C9 S8 . 1.784(4) ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 O10 . 1.213(4) ? C10 O11 . 1.323(5) ? C10 C92 . 1.502(5) ? C12 O11 . 1.448(5) ? C12 H12A . 0.9600 ? C12 H12B . 0.9600 ? C12 H12C . 0.9600 ? C51 C56 . 1.390(5) ? C51 C52 . 1.404(5) ? C52 C53 . 1.386(5) ? C52 H52 . 0.9300 ? C53 C54 . 1.385(6) ? C53 H53 . 0.9300 ? C54 C55 . 1.379(6) ? C54 H54 . 0.9300 ? C55 C56 . 1.389(5) ? C55 H55 . 0.9300 ? C56 H56 . 0.9300 ? C61 C62 . 1.401(5) ? C61 C66 . 1.401(5) ? C62 C63 . 1.394(5) ? C62 H62 . 0.9300 ? C63 C64 . 1.387(6) ? C63 H63 . 0.9300 ? C64 C65 . 1.385(6) ? C64 H64 . 0.9300 ? C65 C66 . 1.383(5) ? C65 H65 . 0.9300 ? C66 H66 . 0.9300 ? C91 C96 . 1.395(5) ? C91 C92 . 1.400(5) ? C92 C93 . 1.398(5) ? C93 C94 . 1.384(6) ? C93 H93 . 0.9300 ? C94 C95 . 1.381(6) ? C94 H94 . 0.9300 ? C95 C96 . 1.382(6) ? C95 H95 . 0.9300 ? C96 H96 . 0.9300 ? N1 N2 . 1.331(4) ? N7 S8 . 1.636(3) ? N7 H7 . 0.90(5) ? O1 S8 . 1.425(3) ? O2 S8 . 1.434(3) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C9 H9A N4 . 0.97 2.41 3.047(4) 123 y C9 H9B O10 . 0.97 2.14 2.825(5) 126 y C93 H93 O11 . 0.93 2.34 2.678(5) 101 y N7 H7 O10 3_666 0.90(5) 1.99(5) 2.893(4) 175(4) y C12 H12 N2 3_666 0.96 2.60 3.512(5) 159 y C63 H63 O2 4_666 0.93 2.54 3.360(4) 147 y C95 H95 N1 1_455 0.93 2.61 3.505(5) 162 y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N4 C5 C6 N1 . . . . 2.4(5) ? C51 C5 C6 N1 . . . . -177.1(3) ? N4 C5 C6 C61 . . . . -177.2(3) ? C51 C5 C6 C61 . . . . 3.3(5) ? N4 C5 C51 C56 . . . . -136.7(4) ? C6 C5 C51 C56 . . . . 42.8(5) ? N4 C5 C51 C52 . . . . 37.7(5) ? C6 C5 C51 C52 . . . . -142.8(4) ? C56 C51 C52 C53 . . . . -2.5(6) ? C5 C51 C52 C53 . . . . -177.1(4) ? C51 C52 C53 C54 . . . . 2.4(7) ? C52 C53 C54 C55 . . . . -1.3(7) ? C53 C54 C55 C56 . . . . 0.4(6) ? C54 C55 C56 C51 . . . . -0.5(6) ? C52 C51 C56 C55 . . . . 1.6(6) ? C5 C51 C56 C55 . . . . 175.9(3) ? N1 C6 C61 C62 . . . . -135.4(3) ? C5 C6 C61 C62 . . . . 44.2(5) ? N1 C6 C61 C66 . . . . 42.4(4) ? C5 C6 C61 C66 . . . . -138.0(3) ? C66 C61 C62 C63 . . . . 1.3(5) ? C6 C61 C62 C63 . . . . 179.1(3) ? C61 C62 C63 C64 . . . . 1.2(5) ? C62 C63 C64 C65 . . . . -1.7(6) ? C63 C64 C65 C66 . . . . -0.2(6) ? C64 C65 C66 C61 . . . . 2.7(6) ? C62 C61 C66 C65 . . . . -3.2(5) ? C6 C61 C66 C65 . . . . 178.9(3) ? S8 C9 C91 C96 . . . . 79.8(3) ? S8 C9 C91 C92 . . . . -102.5(4) ? C96 C91 C92 C93 . . . . -0.9(5) ? C9 C91 C92 C93 . . . . -178.6(3) ? C96 C91 C92 C10 . . . . 178.8(3) ? C9 C91 C92 C10 . . . . 1.1(5) ? O10 C10 C92 C93 . . . . -167.7(4) ? O11 C10 C92 C93 . . . . 12.3(5) ? O10 C10 C92 C91 . . . . 12.6(6) ? O11 C10 C92 C91 . . . . -167.4(3) ? C91 C92 C93 C94 . . . . -0.2(6) ? C10 C92 C93 C94 . . . . -179.9(3) ? C92 C93 C94 C95 . . . . 0.7(6) ? C93 C94 C95 C96 . . . . -0.1(6) ? C94 C95 C96 C91 . . . . -1.0(6) ? C92 C91 C96 C95 . . . . 1.5(6) ? C9 C91 C96 C95 . . . . 179.4(3) ? C5 C6 N1 N2 . . . . 0.1(5) ? C61 C6 N1 N2 . . . . 179.7(3) ? C6 N1 N2 C3 . . . . -2.3(5) ? N4 C3 N2 N1 . . . . 2.2(5) ? N7 C3 N2 N1 . . . . 179.6(3) ? C6 C5 N4 C3 . . . . -2.5(5) ? C51 C5 N4 C3 . . . . 177.1(3) ? N2 C3 N4 C5 . . . . 0.2(5) ? N7 C3 N4 C5 . . . . -177.1(3) ? N4 C3 N7 S8 . . . . -5.3(5) ? N2 C3 N7 S8 . . . . 177.1(3) ? O10 C10 O11 C12 . . . . -1.3(5) ? C92 C10 O11 C12 . . . . 178.6(3) ? C3 N7 S8 O1 . . . . -56.5(3) ? C3 N7 S8 O2 . . . . 175.0(3) ? C3 N7 S8 C9 . . . . 59.4(3) ? C91 C9 S8 O1 . . . . -64.9(3) ? C91 C9 S8 O2 . . . . 67.6(3) ? C91 C9 S8 N7 . . . . 178.8(2) ? _cod_database_fobs_code 2022651