#------------------------------------------------------------------------------ #$Date: 2023-05-13 03:36:26 +0200 (Sat, 13 May 2023) $ #$Revision: 283743 $ #$URL: svn://www.crystallography.net/cod/cif/2/02/27/2022766.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_2022766 loop_ _publ_author_name 'Banna, Md. Hasan Al' 'Sheikh, Md. Chanmiya' 'Miyatake, Ryuta' 'Howlader, Md. Belayet Hossain' 'Zangrando, Ennio' _publ_section_title ; Crystal structure of 4-[(4-methylbenzyl)oxy]-N′-(4-nitrobenzylidene)benzohydrazide: a new hydrazone derivative ; _journal_coeditor_code WM5682 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E Crystallographic Communications' _journal_paper_doi 10.1107/S2056989023003948 _journal_volume 79 _journal_year 2023 _chemical_formula_iupac 'C22 H19 N3 O4' _chemical_formula_moiety 'C22 H19 N3 O4' _chemical_formula_sum 'C22 H19 N3 O4' _chemical_formula_weight 389.40 _chemical_name_systematic ; 4-[(4-Methylbenzyl)oxy]-N'-(4-nitrobenzylidene)benzohydrazide ; _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2019/2 _cell_angle_alpha 90 _cell_angle_beta 96.585(7) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.9485(8) _cell_length_b 5.0612(5) _cell_length_c 20.949(2) _cell_measurement_reflns_used 5984 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.45 _cell_measurement_theta_min 2.29 _cell_volume 942.52(16) _computing_cell_refinement ; RAPID-AUTO (Rigaku, 2018) ; _computing_data_collection ; RAPID-AUTO (Rigaku, 2018) ; _computing_data_reduction ; RAPID-AUTO (Rigaku, 2018) ; _computing_molecular_graphics ; DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX (Farrugia, 2012) ; _computing_structure_refinement ; SHELXL (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_unetI/netI 0.0645 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 9086 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.469 _diffrn_reflns_theta_min 1.957 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_correction_T_min 0.749 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (ABSCOR; Higashi, 1995) ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.372 _exptl_crystal_description platel _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.189 _refine_diff_density_min -0.156 _refine_ls_abs_structure_details ; Flack x determined using 741 quotients [(I^+^)-(I^-^)]/[(I^+^)+(I^-^)] (Parsons et al., 2013) ; _refine_ls_abs_structure_Flack -0.8(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 266 _refine_ls_number_reflns 3799 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0528 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.0221P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1136 _refine_ls_wR_factor_ref 0.1255 _reflns_number_gt 2635 _reflns_number_total 3799 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file wm5682sup1.cif _cod_data_source_block I _cod_original_cell_volume 942.54(16) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2022766 _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_estimated_absorpt_t_min 0.972 _shelx_estimated_absorpt_t_max 0.997 _shelx_hkl_file ; 0 0 2 0.10 0.15 0 0 -2 -0.17 0.19 0 0 3 111.87 1.46 0 0 -3 112.24 1.69 0 0 4 39.83 1.09 0 0 -4 39.37 1.11 0 0 5 166.36 3.35 0 0 -5 161.51 2.77 0 0 6 3.12 0.60 0 0 -6 2.21 0.60 0 0 7 0.13 0.54 0 0 -7 -1.08 0.86 0 0 8 3.73 0.95 0 0 -8 -0.57 0.96 0 0 9 52.11 1.91 0 0 -9 53.04 1.45 0 0 10 200.47 4.13 0 0 -10 195.53 4.51 0 0 11 896.85 26.08 0 0 -11 932.66 28.15 0 0 12 77.36 2.68 0 0 -12 71.72 2.06 0 0 13 22.44 1.24 0 0 -13 22.35 1.31 0 0 14 125.24 3.23 0 0 -14 125.18 4.12 0 0 15 50.13 2.67 0 0 -15 52.00 2.80 0 0 16 80.68 3.61 0 0 -16 87.64 2.83 0 0 17 90.46 3.10 0 0 -17 93.40 3.14 0 0 18 4.29 1.41 0 0 -18 -1.60 2.42 0 0 19 37.09 3.29 0 0 -19 45.93 3.46 0 0 20 5.40 2.56 0 0 -20 7.87 1.79 0 0 21 46.41 2.77 0 0 -21 45.45 2.84 0 0 22 8.09 1.96 0 0 -22 5.07 3.05 0 0 23 11.47 3.29 0 0 -23 9.49 2.59 0 0 -23 12.31 2.20 0 0 24 1.44 2.07 0 0 -24 3.65 2.37 0 0 -24 0.77 2.05 0 0 25 5.02 2.18 0 0 -25 4.65 3.93 0 0 -25 -2.43 3.34 0 0 26 3.66 3.37 0 0 -26 3.03 2.76 0 0 -26 -5.73 3.34 0 0 -27 5.59 2.51 0 1 0 0.70 0.42 0 1 0 -0.17 0.23 0 1 1 22.60 0.81 0 1 1 22.70 0.54 0 1 -1 22.69 0.52 0 -1 -1 21.48 0.65 0 1 2 292.49 5.29 0 1 2 288.22 4.32 0 1 -2 285.18 4.82 0 -1 2 282.90 4.53 0 -1 -2 282.65 4.09 0 -1 -2 284.37 4.74 0 1 3 166.76 2.84 0 1 3 157.90 2.32 0 1 -3 165.16 2.59 0 -1 3 160.00 2.59 0 -1 -3 166.44 2.52 0 -1 -3 164.32 2.80 0 1 4 258.75 4.58 0 1 4 252.35 4.09 0 1 -4 261.03 4.90 0 -1 4 254.00 4.81 0 -1 -4 257.34 4.24 0 -1 -4 252.65 5.16 0 1 5 233.33 3.99 0 1 -5 239.54 4.68 0 -1 5 235.97 4.65 0 -1 -5 232.52 3.66 0 -1 -5 228.54 4.32 0 1 6 246.89 4.24 0 1 -6 253.79 5.18 0 -1 6 253.37 4.66 0 -1 -6 248.15 4.48 0 -1 -6 261.20 5.76 0 1 7 111.96 2.32 0 1 -7 116.29 2.76 0 -1 7 108.36 2.71 0 -1 -7 109.67 2.26 0 -1 -7 102.26 2.35 0 1 8 3.70 1.00 0 1 -8 8.19 0.81 0 -1 8 6.98 0.83 0 -1 -8 6.12 0.62 0 -1 -8 7.34 0.90 0 1 9 45.01 1.85 0 1 -9 46.14 1.54 0 -1 9 49.62 1.47 0 -1 -9 46.49 1.67 0 -1 -9 43.49 2.21 0 1 -10 17.20 1.54 0 -1 10 14.50 1.04 0 -1 -10 14.98 1.24 0 -1 -10 15.19 1.69 0 1 11 105.86 2.98 0 1 -11 102.51 2.63 0 -1 11 99.00 2.56 0 -1 -11 100.85 2.31 0 -1 -11 98.93 3.55 0 1 12 56.16 2.24 0 1 -12 61.05 2.61 0 -1 12 53.95 1.88 0 -1 -12 54.09 1.63 0 -1 -12 63.23 2.17 0 1 13 77.07 2.14 0 1 -13 79.89 2.39 0 -1 13 73.14 2.27 0 -1 -13 78.56 2.14 0 -1 -13 86.62 3.55 0 1 14 105.57 3.70 0 1 -14 109.20 4.38 0 -1 14 102.34 3.05 0 -1 -14 102.58 2.67 0 -1 -14 101.22 4.37 0 1 15 16.26 1.33 0 1 -15 18.59 1.60 0 -1 15 16.19 1.50 0 -1 -15 20.65 1.33 0 -1 -15 21.48 2.53 0 1 16 36.60 2.53 0 1 -16 42.29 3.20 0 -1 16 35.12 2.01 0 -1 -16 35.56 1.75 0 -1 -16 29.35 3.09 0 1 17 33.60 2.76 0 1 -17 31.47 3.36 0 -1 17 34.41 2.13 0 -1 -17 34.02 1.83 0 -1 -17 33.72 3.70 0 1 18 46.02 2.24 0 1 -18 45.17 2.55 0 -1 18 48.55 3.51 0 -1 -18 42.90 2.98 0 -1 -18 43.74 2.99 0 1 19 45.34 3.35 0 1 -19 47.03 4.16 0 -1 19 45.55 3.81 0 -1 -19 46.12 3.28 0 -1 -19 44.92 3.12 0 1 20 2.00 1.52 0 1 -20 3.92 1.94 0 -1 20 -0.25 2.65 0 -1 -20 4.72 2.28 0 -1 -20 2.02 2.10 0 1 21 9.54 2.71 0 1 -21 8.83 2.10 0 -1 21 9.43 2.04 0 -1 -21 8.79 2.66 0 -1 -21 12.20 2.49 0 1 22 0.91 2.58 0 1 -22 2.41 3.01 0 -1 22 -0.53 1.93 0 -1 -22 2.28 1.71 0 -1 -22 1.59 3.54 0 1 23 6.74 1.91 0 1 -23 4.81 2.30 0 -1 23 6.91 2.16 0 -1 -23 1.74 1.87 0 -1 -23 7.65 3.90 0 1 24 4.25 3.04 0 1 -24 5.26 2.38 0 -1 24 2.62 3.48 0 -1 -24 4.84 3.06 0 -1 -24 1.38 2.75 0 1 25 -3.22 3.11 0 1 -25 3.56 3.66 0 -1 25 4.99 3.53 0 -1 -25 3.06 3.00 0 -1 -25 1.82 2.91 0 1 26 5.13 2.22 0 1 -26 2.40 2.57 0 -1 26 4.80 2.53 0 -1 -26 0.88 3.30 0 -1 -26 2.80 3.12 0 2 0 24.41 0.71 0 2 0 26.16 0.91 0 2 1 202.20 3.71 0 2 1 208.68 3.65 0 2 -1 207.68 3.96 0 2 -1 209.01 4.06 0 -2 -1 215.41 4.37 0 2 2 125.39 2.37 0 2 2 127.98 2.24 0 2 -2 125.37 2.22 0 -2 -2 119.59 2.04 0 -2 -2 128.39 2.84 0 2 3 189.32 4.20 0 2 3 186.62 3.28 0 2 -3 191.10 3.89 0 -2 -3 191.59 3.49 0 -2 -3 188.72 4.22 0 2 4 226.21 4.57 0 2 4 218.98 4.00 0 2 -4 222.22 4.28 0 -2 4 224.47 4.45 0 -2 -4 211.72 4.03 0 -2 -4 226.11 5.19 0 2 5 3.46 1.09 0 2 5 0.74 0.59 0 2 -5 0.75 0.66 0 -2 5 -0.47 0.70 0 -2 -5 0.50 0.68 0 -2 -5 2.65 0.73 0 2 6 157.31 4.22 0 2 6 153.93 2.99 0 2 -6 161.86 3.33 0 -2 6 154.32 3.90 0 -2 -6 159.02 3.14 0 -2 -6 161.06 3.54 0 2 7 255.99 4.93 0 2 -7 263.80 5.61 0 -2 7 258.37 6.41 0 -2 -7 257.92 5.15 0 -2 -7 258.77 6.74 0 2 8 282.75 6.18 0 2 -8 295.94 6.47 0 -2 8 289.79 6.48 0 -2 -8 274.47 5.94 0 -2 -8 285.69 6.81 0 2 9 16.28 1.21 0 2 -9 16.15 1.63 0 -2 9 17.43 1.68 0 -2 -9 18.44 0.84 0 -2 -9 18.72 1.92 0 2 10 26.42 1.46 0 2 -10 31.19 1.93 0 -2 10 24.35 1.91 0 -2 -10 25.89 1.00 0 -2 -10 27.34 1.54 0 2 11 83.05 2.56 0 2 -11 80.55 2.37 0 -2 11 75.00 2.32 0 -2 -11 72.84 2.24 0 -2 -11 83.06 3.54 0 2 12 1.59 1.31 0 2 -12 -1.29 1.68 0 -2 12 0.35 1.07 0 -2 -12 -0.06 0.69 0 -2 -12 -0.20 1.84 0 2 13 41.20 2.17 0 2 -13 41.11 1.94 0 -2 13 40.23 2.67 0 -2 -13 38.27 1.85 0 -2 -13 40.24 2.17 0 2 14 120.84 3.34 0 2 -14 136.17 5.15 0 -2 14 121.71 4.85 0 -2 -14 118.36 3.85 0 -2 -14 131.02 4.27 0 2 15 60.67 2.97 0 2 -15 68.34 2.91 0 -2 15 70.99 3.68 0 -2 -15 62.73 2.09 0 -2 -15 68.18 3.02 0 2 16 53.08 3.11 0 2 -16 55.01 3.95 0 -2 16 58.17 3.88 0 -2 -16 58.65 2.08 0 -2 -16 59.42 3.12 0 2 17 36.70 2.00 0 2 -17 34.93 2.48 0 -2 17 41.27 3.55 0 -2 -17 38.27 1.87 0 -2 -17 34.73 2.79 0 2 18 54.10 3.31 0 2 -18 52.65 4.21 0 -2 18 49.86 4.07 0 -2 -18 51.04 3.03 0 -2 -18 49.88 3.33 0 2 -19 0.04 1.95 0 -2 19 4.77 2.70 0 -2 -19 5.94 2.01 0 -2 -19 2.86 2.16 0 2 20 6.50 2.42 0 2 -20 7.06 3.24 0 -2 20 9.23 3.16 0 -2 -20 7.56 2.22 0 -2 -20 7.62 2.45 0 2 21 3.73 1.63 0 2 -21 0.87 3.38 0 -2 21 0.85 3.19 0 -2 -21 4.06 2.29 0 -2 -21 5.89 2.40 0 2 22 6.34 2.76 0 2 -22 5.58 2.33 0 -2 22 4.68 2.17 0 -2 -22 4.22 1.65 0 -2 -22 1.04 3.88 0 2 23 2.53 2.70 0 2 -23 4.03 3.62 0 -2 23 1.50 2.29 0 -2 -23 -1.15 1.65 0 -2 -23 2.16 4.15 0 2 24 0.48 2.81 0 2 -24 0.10 2.56 0 -2 -24 -6.98 4.40 0 -2 24 1.02 2.22 0 2 25 4.82 3.18 0 2 -25 5.36 2.78 0 -2 25 2.05 2.57 0 -2 -25 5.80 2.01 0 -2 -25 2.37 4.88 0 3 0 -0.39 1.00 0 3 0 0.95 0.83 0 3 0 0.15 0.59 0 3 1 4.08 0.76 0 3 1 2.84 0.85 0 3 -1 3.15 0.67 0 3 -1 3.47 0.62 0 3 -1 3.85 0.65 0 3 2 42.51 1.37 0 3 2 48.35 1.13 0 3 -2 44.40 1.69 0 3 -2 47.26 1.75 0 3 3 29.97 1.72 0 3 3 27.92 0.88 0 3 -3 27.63 1.50 0 3 -3 29.58 1.40 0 -3 -3 29.71 1.23 0 3 4 32.31 1.88 0 3 4 33.73 1.25 0 3 -4 35.69 1.71 0 -3 -4 30.09 1.90 0 3 5 62.07 2.58 0 3 5 65.77 1.78 0 3 -5 66.28 2.38 0 -3 -5 65.61 1.91 0 -3 -5 59.29 2.52 0 3 6 15.69 1.74 0 3 6 14.85 0.70 0 3 -6 11.22 1.56 0 -3 -6 12.43 1.15 0 -3 -6 16.93 1.74 0 3 7 30.77 2.21 0 3 -7 26.70 1.33 0 -3 -7 26.97 1.37 0 -3 -7 28.45 1.52 0 3 8 3.45 1.08 0 3 8 2.23 0.64 0 3 -8 0.40 0.98 0 -3 8 1.45 1.02 0 -3 -8 1.75 0.97 0 -3 -8 1.98 1.13 0 3 9 8.85 1.20 0 3 -9 8.06 1.75 0 -3 9 8.50 1.87 0 -3 -9 8.20 0.80 0 -3 -9 11.26 2.08 0 3 10 2.15 1.14 0 3 -10 2.71 1.11 0 -3 10 2.97 1.74 0 -3 -10 1.91 1.10 0 -3 -10 -0.38 1.29 0 3 11 3.78 1.25 0 3 -11 0.83 1.23 0 -3 11 1.21 1.24 0 -3 -11 1.82 1.20 0 -3 -11 0.48 2.14 0 3 12 8.77 1.55 0 3 -12 9.98 2.29 0 -3 12 8.33 2.22 0 -3 -12 8.15 1.47 0 -3 -12 14.01 2.53 0 3 13 23.99 2.26 0 3 -13 21.40 1.93 0 -3 13 24.32 2.74 0 -3 -13 21.66 1.79 0 -3 -13 20.69 2.08 0 3 14 6.37 1.77 0 3 -14 10.00 2.41 0 -3 14 6.92 1.65 0 -3 -14 8.07 1.59 0 -3 -14 5.00 1.84 0 3 15 109.39 3.39 0 3 -15 119.92 4.38 0 -3 15 111.63 4.18 0 -3 -15 112.88 3.84 0 -3 -15 107.91 6.10 0 3 16 13.38 2.19 0 3 -16 14.07 3.03 0 -3 16 16.64 1.97 0 -3 -16 12.96 1.31 0 -3 -16 15.37 3.32 0 3 17 4.99 2.06 0 3 -17 6.01 1.88 0 -3 17 4.17 1.88 0 -3 -17 3.89 1.89 0 -3 -17 10.08 3.39 0 3 18 0.66 1.33 0 3 -18 -3.62 2.92 0 -3 18 -0.45 2.79 0 -3 -18 -1.34 1.81 0 -3 -18 5.45 3.26 0 3 19 5.64 2.51 0 3 -19 7.53 2.32 0 -3 19 11.73 3.36 0 -3 -19 8.44 2.30 0 -3 -19 11.28 3.88 0 3 20 4.21 2.48 0 3 -20 0.02 3.51 0 -3 20 8.90 3.47 0 -3 -20 7.14 2.37 0 -3 -20 5.31 3.80 0 3 21 5.33 1.68 0 3 -21 0.81 3.59 0 -3 21 0.64 3.47 0 -3 -21 1.00 1.61 0 -3 -21 4.12 4.03 0 3 22 3.35 2.92 0 3 -22 11.08 2.64 0 -3 22 7.57 3.86 0 -3 -22 5.14 1.75 0 -3 -22 -1.58 4.53 0 3 23 -1.12 1.79 0 3 -23 2.32 3.83 0 -3 23 -3.70 2.55 0 -3 -23 0.48 1.67 0 -3 -23 3.15 4.40 0 3 24 6.70 3.08 0 -3 -24 1.24 5.07 0 4 0 2.39 0.98 0 4 0 1.33 0.80 0 4 0 0.67 1.32 0 4 1 0.71 0.99 0 4 1 0.81 1.11 0 4 1 0.85 1.29 0 4 -1 1.87 0.94 0 4 -1 0.34 0.82 0 4 -1 0.93 1.33 0 4 2 29.45 1.51 0 4 2 29.83 1.62 0 4 -2 30.11 1.97 0 4 -2 27.98 1.33 0 4 -2 30.80 1.41 0 4 3 16.66 1.39 0 4 3 19.42 1.00 0 4 -3 18.71 1.75 0 4 -3 16.87 1.74 0 4 -3 18.06 1.25 0 4 4 64.39 2.27 0 4 -4 61.84 2.54 0 4 -4 61.44 2.10 0 4 -4 62.23 2.11 0 4 5 2.62 1.87 0 4 5 1.49 0.75 0 4 -5 4.12 1.63 0 4 -5 3.22 1.43 0 -4 -5 4.04 1.75 0 4 6 6.08 2.01 0 4 6 5.58 1.23 0 4 -6 1.53 1.79 0 4 -6 4.25 1.54 0 -4 -6 6.82 1.92 0 4 7 2.99 1.40 0 4 7 2.68 1.17 0 4 -7 3.61 1.21 0 -4 -7 3.40 2.07 0 4 8 20.14 1.75 0 4 8 19.85 1.57 0 4 -8 15.94 2.30 0 -4 -8 20.38 1.71 0 -4 -8 20.16 1.78 0 4 9 26.50 1.25 0 4 -9 23.31 2.59 0 -4 -9 22.77 1.83 0 -4 -9 26.74 2.96 0 4 10 13.50 1.66 0 4 -10 14.19 1.68 0 -4 -10 15.10 1.70 0 -4 -10 15.75 1.82 0 4 11 -0.25 1.45 0 4 -11 3.96 2.19 0 -4 -11 1.34 0.96 0 -4 -11 5.12 2.44 0 4 12 4.82 1.68 0 4 -12 7.85 1.66 0 -4 -12 4.55 1.61 0 -4 -12 6.98 1.88 0 4 13 20.99 2.20 0 4 -13 23.83 3.17 0 -4 -13 19.72 2.02 0 -4 -13 14.93 3.50 0 4 14 7.04 1.31 0 4 -14 6.56 1.91 0 -4 -14 8.42 1.20 0 -4 -14 4.28 3.30 0 4 15 20.38 1.72 0 4 -15 22.87 3.65 0 -4 -15 24.65 2.21 0 -4 -15 25.14 2.70 0 4 16 7.97 2.25 0 4 -16 9.66 2.13 0 -4 16 8.20 2.13 0 -4 -16 6.50 1.33 0 -4 -16 4.03 2.37 0 4 17 17.30 2.64 0 4 -17 22.32 3.82 0 -4 17 16.21 2.54 0 -4 -17 16.02 2.36 0 -4 -17 14.56 2.80 0 4 18 16.43 2.63 0 4 -18 15.82 2.68 0 -4 18 9.16 2.57 0 -4 -18 11.45 2.33 0 -4 -18 14.54 4.34 0 4 19 1.75 1.68 0 4 -19 6.58 3.68 0 -4 19 5.94 2.44 0 -4 -19 4.88 1.49 0 -4 -19 7.89 4.16 0 4 20 3.14 2.61 0 4 -20 0.66 2.51 0 -4 20 11.55 3.76 0 -4 -20 4.12 1.57 0 -4 -20 -3.47 4.22 0 4 21 2.87 1.82 0 4 -21 6.02 2.72 0 -4 21 4.14 4.06 0 -4 -21 4.91 2.43 0 -4 -21 4.16 4.49 0 5 0 1.39 1.91 0 5 0 -1.70 1.52 0 5 0 0.78 1.07 0 5 1 4.68 2.10 0 5 1 5.82 1.66 0 5 1 8.37 1.81 0 5 -1 3.99 2.02 0 5 -1 5.50 1.71 0 5 -1 4.18 1.84 0 5 2 61.97 3.60 0 5 2 59.16 2.12 0 5 2 58.11 3.04 0 5 -2 58.65 2.39 0 5 -2 58.64 3.01 0 5 -2 60.45 3.18 0 5 3 36.48 2.16 0 5 3 35.75 1.58 0 5 3 34.63 2.39 0 5 -3 33.37 1.87 0 5 -3 38.28 1.85 0 5 -3 37.91 1.98 0 5 4 4.45 2.40 0 5 4 5.94 1.06 0 5 4 5.40 1.18 0 5 -4 4.31 2.02 0 5 -4 6.19 1.30 0 5 -4 5.39 2.07 0 5 5 9.90 2.56 0 5 5 10.87 1.71 0 5 -5 6.19 2.04 0 5 -5 8.71 2.20 0 5 -5 10.29 2.26 0 5 6 4.33 1.75 0 5 6 7.25 1.63 0 5 -6 2.70 2.01 0 5 -6 6.70 2.12 0 5 -6 7.85 1.54 0 5 7 7.07 2.60 0 5 7 7.83 1.61 0 5 -7 9.00 2.02 0 5 -7 7.53 1.61 0 5 -7 8.19 2.45 0 5 8 17.62 1.88 0 5 -8 16.17 1.57 0 5 -8 15.17 1.83 0 -5 -8 13.64 3.18 0 5 9 20.55 2.10 0 5 -9 20.11 3.11 0 5 -9 22.04 1.75 0 -5 -9 25.62 2.36 0 5 10 3.88 1.75 0 5 -10 2.63 1.71 0 5 -10 2.36 2.10 0 -5 -10 5.88 2.84 0 5 11 5.43 1.89 0 5 -11 8.29 2.78 0 -5 -11 7.85 2.13 0 5 12 4.94 1.88 0 5 -12 3.74 1.92 0 -5 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2 6 51.14 1.92 2 2 6 48.35 0.89 -2 2 -6 48.75 2.27 -2 -2 -6 50.74 0.88 -2 -2 -6 48.56 1.85 2 2 7 37.77 1.76 2 2 7 37.66 0.92 -2 2 -7 39.40 2.14 -2 -2 -7 37.82 0.86 -2 -2 -7 37.45 1.70 2 2 8 60.45 2.33 2 2 8 61.94 1.37 -2 2 -8 60.63 2.65 -2 -2 -8 63.76 1.31 -2 -2 -8 68.14 3.04 2 2 9 37.95 1.91 2 2 9 32.11 1.11 -2 2 -9 30.38 2.30 -2 -2 -9 32.82 1.06 -2 -2 -9 35.70 1.83 2 2 10 67.74 3.30 2 2 10 59.38 1.68 -2 2 -10 63.10 2.24 2 -2 10 59.84 2.20 -2 -2 -10 60.48 1.58 -2 -2 -10 64.97 3.49 2 2 11 12.02 1.11 -2 2 -11 10.60 1.29 2 -2 11 12.91 1.97 -2 -2 -11 9.29 0.98 -2 -2 -11 13.67 1.59 2 2 12 31.35 1.52 -2 2 -12 28.50 2.60 2 -2 12 29.08 1.91 -2 -2 -12 31.26 1.42 -2 -2 -12 32.75 3.17 2 2 13 18.95 1.03 -2 2 -13 21.53 2.56 2 -2 13 17.79 1.72 -2 -2 -13 19.63 1.37 -2 -2 -13 24.20 2.95 2 2 14 27.01 1.77 -2 2 -14 29.90 1.97 2 -2 14 27.70 2.88 -2 -2 -14 28.88 1.70 -2 -2 -14 25.99 2.33 2 2 15 51.00 2.50 -2 2 -15 54.66 3.74 2 -2 15 57.71 3.84 -2 -2 -15 55.77 2.44 -2 -2 -15 58.87 3.09 2 2 16 117.88 3.26 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14.28 2.24 -10 -1 -5 12.79 1.68 -10 -1 -5 12.42 1.60 -10 1 -6 1.41 1.65 10 1 6 1.81 3.30 -10 1 -6 1.60 2.65 10 -1 6 2.83 1.92 10 1 7 5.08 2.38 -10 1 -7 5.82 2.72 -10 1 -7 6.02 2.00 10 1 8 15.15 2.67 -10 1 -8 16.75 2.01 -10 1 -8 13.17 2.10 10 1 9 1.21 3.51 -10 1 -9 1.77 2.50 -10 1 -9 -0.69 2.82 10 1 10 -1.89 3.66 -10 1 -10 1.70 1.73 -10 1 -10 3.19 2.83 -10 2 13 -0.91 3.68 10 2 -13 0.94 2.36 10 -2 -13 3.87 3.54 -10 -2 13 0.04 2.65 -10 2 12 0.15 2.20 10 2 -12 0.84 1.46 10 -2 -12 0.22 2.27 -10 -2 12 -0.34 1.64 -10 2 11 5.87 2.27 10 2 -11 2.55 2.22 10 -2 -11 2.21 3.43 -10 -2 11 -0.85 2.42 -10 2 10 8.39 3.57 10 2 -10 5.20 2.22 10 -2 -10 9.11 2.50 -10 -2 10 9.25 2.45 -10 2 9 -2.20 1.96 10 2 -9 2.19 1.79 10 -2 -9 3.38 3.14 -10 -2 9 -0.09 2.03 10 2 -8 2.76 2.62 -10 2 8 7.75 3.15 10 2 -8 2.05 1.20 10 -2 -8 4.26 2.13 -10 -2 8 1.64 1.30 10 2 -7 0.23 3.89 -10 2 7 2.16 2.06 10 2 -7 1.12 1.08 10 -2 -7 2.16 3.15 -10 -2 7 -0.27 1.61 10 2 -6 1.18 2.39 10 2 -6 0.20 0.97 -10 2 6 -5.16 2.85 10 -2 -6 1.06 1.56 10 -2 -6 4.55 2.12 -10 -2 6 -0.81 1.42 10 2 -5 3.62 3.48 10 2 -5 -0.16 1.38 -10 2 5 2.02 1.88 -10 -2 5 0.50 1.48 10 2 -4 1.38 2.42 -10 2 4 2.72 2.95 -10 -2 4 1.88 0.91 10 2 -3 -3.64 3.58 -10 2 3 4.59 2.01 10 2 -2 3.30 3.82 -10 2 2 5.89 3.10 10 2 -1 -0.69 2.33 -10 2 1 2.96 2.85 10 2 0 2.16 3.48 -10 2 0 -1.05 1.79 10 2 1 5.61 3.76 -10 2 -1 0.79 2.76 10 2 2 -1.56 2.35 -10 2 -2 0.48 1.83 10 2 3 4.30 3.76 -10 2 -3 1.83 2.98 -10 2 -3 3.37 2.13 10 2 4 -7.48 3.87 -10 2 -4 -1.60 1.99 -10 2 -4 -4.74 3.28 10 2 5 2.39 2.50 -10 2 -5 0.48 2.83 -10 2 -5 -0.56 3.14 10 2 6 -0.26 2.45 -10 2 -6 0.44 2.86 -10 2 -6 0.98 2.06 10 2 7 3.62 3.80 -10 2 -7 0.18 1.95 -10 2 -7 1.81 3.27 10 2 8 0.59 2.54 -10 2 -8 2.92 2.98 -10 2 -8 -4.61 3.27 10 3 -8 4.35 2.97 -10 3 8 2.96 2.37 10 -3 -8 -1.68 2.62 10 3 -7 -0.29 4.36 -10 3 7 6.64 3.53 10 3 -6 4.08 3.06 -10 3 6 5.31 2.39 10 3 -5 -0.92 4.21 -10 3 5 4.20 2.33 10 3 -4 5.32 2.87 -10 3 4 5.48 3.61 10 3 -3 -1.33 4.19 -10 3 3 -0.96 2.24 10 3 -2 -0.97 2.67 -10 3 2 1.79 3.23 10 3 -1 5.44 4.22 -10 3 1 -1.01 2.13 10 3 0 -0.36 2.79 -10 3 0 5.92 3.43 10 3 1 -4.94 2.73 -10 3 -1 5.93 3.19 10 3 2 -6.38 4.30 -10 3 -2 3.00 2.16 10 3 3 0.08 2.85 -10 3 -3 2.65 3.52 -10 3 -3 3.86 2.49 11 0 -11 0.24 2.97 -11 0 11 2.60 2.09 11 0 -10 5.70 2.05 -11 0 10 5.51 3.22 11 0 -9 17.61 3.39 -11 0 9 12.77 2.27 11 0 -8 -1.54 2.70 -11 0 8 2.49 2.79 11 0 -7 2.31 3.32 11 0 -7 5.55 1.85 -11 0 7 4.28 1.84 11 0 -6 1.58 1.97 11 0 -6 -1.50 2.64 -11 0 6 -2.02 2.58 11 0 -5 1.50 2.05 -11 0 5 4.11 1.75 11 0 -4 0.10 2.90 -11 0 4 1.12 2.39 11 0 -3 -0.69 2.84 -11 0 3 -1.83 2.39 11 0 -2 1.78 2.87 -11 0 2 1.53 2.26 11 0 -1 -1.01 1.85 -11 0 1 1.04 2.16 11 0 0 -0.21 1.83 -11 0 0 0.43 1.42 11 0 1 -3.12 2.97 -11 0 -1 1.09 2.12 11 0 2 1.49 2.84 -11 0 -2 1.18 1.39 -11 0 -2 0.77 2.39 11 0 3 3.85 2.91 -11 0 -3 0.12 2.08 -11 0 -3 -0.56 2.36 11 0 4 2.35 2.93 -11 0 -4 1.35 1.45 -11 0 -4 1.26 1.51 11 0 5 0.98 2.84 -11 0 -5 -0.82 2.13 -11 0 -5 -0.62 1.47 -11 1 10 11.14 3.45 11 1 -10 3.87 2.66 11 -1 -10 4.63 2.27 -11 -1 10 0.69 1.99 -11 1 9 -0.37 2.16 11 1 -9 2.20 1.60 11 -1 -9 4.88 3.14 -11 -1 9 2.51 2.74 11 1 -8 3.18 2.59 -11 1 8 4.90 3.19 11 1 -8 2.22 1.68 11 -1 -8 3.84 2.23 -11 -1 8 3.95 2.59 11 1 -7 7.07 3.66 11 1 -7 3.69 2.38 -11 1 7 1.56 2.06 11 -1 -7 4.02 2.70 11 -1 -7 10.22 3.26 -11 -1 7 3.67 2.47 11 1 -6 7.07 3.49 11 1 -6 -0.85 2.21 -11 1 6 2.02 2.86 11 -1 -6 2.70 2.47 11 -1 -6 -0.12 2.06 -11 -1 6 1.11 2.33 11 1 -5 2.01 2.27 -11 1 5 0.75 1.78 11 -1 -5 0.22 2.34 -11 -1 5 -0.17 1.39 11 1 -4 -2.21 3.33 -11 1 4 -0.14 2.75 11 -1 -4 -0.35 2.15 -11 -1 4 1.47 1.95 -11 1 3 9.43 2.99 11 1 -3 9.53 3.73 11 -1 -3 6.60 2.41 -11 1 2 4.27 2.74 11 1 -2 3.80 2.27 11 -1 -2 2.14 2.24 -11 -1 2 2.93 1.85 -11 1 1 0.70 2.68 11 1 -1 7.45 3.57 11 -1 -1 2.92 2.14 -11 1 0 -0.59 1.74 11 1 0 2.28 3.34 11 -1 0 -1.18 1.99 -11 -1 0 -0.42 1.51 11 1 1 -0.85 2.27 -11 1 -1 -2.17 2.68 11 1 2 0.57 2.26 -11 1 -2 0.39 1.74 11 1 3 1.46 3.59 -11 1 -3 2.00 2.91 -11 1 -3 6.99 3.05 11 1 4 2.86 3.68 -11 1 -4 2.22 2.82 -11 1 -4 5.81 3.10 11 2 -5 9.74 4.43 11 2 -4 -2.65 2.61 -11 2 4 -3.84 2.14 11 2 -3 2.85 4.08 -11 2 3 1.47 3.11 11 2 -2 0.76 2.53 -11 2 2 0.99 2.02 11 2 -1 -0.77 2.63 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 51020 _shelx_res_file ; TITL SH197 shelx.res created by SHELXL-2019/2 at 14:38:37 on 03-Apr-2023 CELL 0.71075 8.9485 5.0612 20.9493 90.000 96.585 90.000 ZERR 2.00 0.0008 0.0005 0.0020 0.000 0.007 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O UNIT 44 38 6 8 MERG 2 OMIT 1 0 0 OMIT -2 0 3 EQIV $1 -x+1, y+1/2, -z+1 HTAB C14 N2_$1 EQIV $2 x, y+1, z HTAB C16 O2_$2 EQIV $3 -x+1, y+1/2, -z HTAB C21 O4_$3 HTAB N1 O2_$2 FMAP 2 PLAN 10 SIZE 0.030 0.280 0.300 ACTA HTAB 2.00000 BOND $H CONF L.S. 10 TEMP -100.00 WGHT 0.063700 0.022100 FVAR 0.57818 O1 4 0.147681 0.542392 0.668165 11.00000 0.05145 0.06063 = 0.03279 -0.00791 0.01394 -0.01278 O2 4 0.307183 0.118821 0.398778 11.00000 0.06054 0.03069 = 0.03206 -0.00153 0.01013 0.00111 O3 4 0.719459 0.395524 0.043326 11.00000 0.07618 0.16798 = 0.04893 -0.00696 0.01990 0.03970 O4 4 0.596553 0.747704 0.009094 11.00000 0.11305 0.08647 = 0.04187 0.00316 0.03236 -0.01466 N1 3 0.361090 0.554177 0.388305 11.00000 0.05715 0.02884 = 0.02594 -0.00166 0.01049 0.00004 H1 2 0.354036 0.723977 0.401070 11.00000 -1.20000 N2 3 0.417304 0.510156 0.330795 11.00000 0.04923 0.03217 = 0.02737 -0.00200 0.00870 0.00073 N3 3 0.637900 0.585966 0.051050 11.00000 0.05938 0.09384 = 0.03846 -0.00849 0.01416 -0.01054 C1 1 -0.101065 0.882275 0.930305 11.00000 0.06526 0.10996 = 0.04341 -0.01756 0.02320 -0.00846 AFIX 137 H1A 2 -0.136189 1.063016 0.920871 11.00000 -1.20000 H1B 2 -0.010078 0.886972 0.961152 11.00000 -1.20000 H1C 2 -0.179652 0.782238 0.948641 11.00000 -1.20000 AFIX 0 C2 1 -0.066037 0.750637 0.869037 11.00000 0.04119 0.06818 = 0.03488 -0.00433 0.01558 -0.01355 C3 1 0.029005 0.542487 0.869826 11.00000 0.09245 0.06924 = 0.03073 0.00802 -0.00159 0.01125 AFIX 43 H3 2 0.074131 0.476727 0.909949 11.00000 -1.20000 AFIX 0 C4 1 0.062152 0.423189 0.813966 11.00000 0.08265 0.06952 = 0.04403 0.00172 -0.00144 0.03372 AFIX 43 H4 2 0.130000 0.278228 0.816291 11.00000 -1.20000 AFIX 0 C5 1 -0.001895 0.511489 0.754704 11.00000 0.03854 0.04921 = 0.03370 -0.00032 0.00898 -0.00542 C6 1 -0.097421 0.718857 0.753526 11.00000 0.06390 0.06500 = 0.03547 0.00061 -0.00241 0.01517 AFIX 43 H6 2 -0.143298 0.783136 0.713380 11.00000 -1.20000 AFIX 0 C7 1 -0.129526 0.838719 0.809362 11.00000 0.05507 0.09375 = 0.04625 -0.01503 0.00020 0.02457 AFIX 43 H7 2 -0.196585 0.984825 0.806939 11.00000 -1.20000 AFIX 0 C8 1 0.034856 0.384644 0.693681 11.00000 0.04810 0.05574 = 0.03659 -0.00222 0.01260 -0.00794 AFIX 23 H8A 2 0.072933 0.203070 0.702463 11.00000 -1.20000 H8B 2 -0.056490 0.374539 0.662284 11.00000 -1.20000 AFIX 0 C9 1 0.182260 0.483962 0.608089 11.00000 0.03845 0.04171 = 0.02816 -0.00031 0.00490 0.00013 C10 1 0.122197 0.273523 0.570520 11.00000 0.04099 0.03738 = 0.03959 -0.00153 0.01214 -0.00525 AFIX 43 H10 2 0.052049 0.156850 0.586470 11.00000 -1.20000 AFIX 0 C11 1 0.165172 0.236204 0.510327 11.00000 0.04729 0.03257 = 0.03491 -0.00688 0.00509 -0.00439 AFIX 43 H11 2 0.123802 0.092481 0.485007 11.00000 -1.20000 AFIX 0 C12 1 0.267869 0.403377 0.485302 11.00000 0.03951 0.02791 = 0.02591 -0.00162 0.00349 0.00448 C13 1 0.328917 0.610331 0.523947 11.00000 0.04674 0.03909 = 0.03110 -0.00010 0.00732 -0.00662 AFIX 43 H13 2 0.399403 0.727021 0.508241 11.00000 -1.20000 AFIX 0 C14 1 0.287577 0.646457 0.584755 11.00000 0.04889 0.04282 = 0.03325 -0.00744 0.00193 -0.00723 AFIX 43 H14 2 0.332136 0.785035 0.610979 11.00000 -1.20000 AFIX 0 C15 1 0.312639 0.345369 0.421051 11.00000 0.03730 0.02969 = 0.02761 -0.00061 0.00059 0.00407 C16 1 0.431653 0.714285 0.296006 11.00000 0.06055 0.03178 = 0.03198 -0.00541 0.01079 -0.00142 AFIX 43 H16 2 0.404496 0.884332 0.310034 11.00000 -1.20000 AFIX 0 C17 1 0.491034 0.680704 0.233834 11.00000 0.05589 0.03589 = 0.03117 -0.00506 0.01137 -0.01373 C18 1 0.587564 0.475403 0.223223 11.00000 0.05438 0.04826 = 0.03757 -0.00138 0.01045 -0.00849 AFIX 43 H18 2 0.620600 0.356662 0.257043 11.00000 -1.20000 AFIX 0 C19 1 0.635783 0.443696 0.163192 11.00000 0.05117 0.05720 = 0.04686 -0.00952 0.01696 -0.00942 AFIX 43 H19 2 0.702781 0.304857 0.155381 11.00000 -1.20000 AFIX 0 C20 1 0.584324 0.618460 0.114853 11.00000 0.05145 0.06758 = 0.03058 -0.00732 0.01442 -0.01931 C21 1 0.489381 0.821679 0.123566 11.00000 0.07911 0.05423 = 0.03170 0.00224 0.01332 -0.01812 AFIX 43 H21 2 0.455193 0.937239 0.089234 11.00000 -1.20000 AFIX 0 C22 1 0.444465 0.854552 0.183620 11.00000 0.08196 0.04018 = 0.03899 0.00251 0.02100 -0.00585 AFIX 43 H22 2 0.380496 0.998273 0.191162 11.00000 -1.20000 AFIX 0 HKLF 4 REM SH197 REM wR2 = 0.1255, GooF = S = 1.035, Restrained GooF = 1.035 for all data REM R1 = 0.0528 for 2635 Fo > 4sig(Fo) and 0.0867 for all 3799 data REM 266 parameters refined using 1 restraints END WGHT 0.0635 0.0400 REM Instructions for potential hydrogen bonds HTAB N1 O2_$2 HTAB C14 N2_$1 HTAB C16 O2_$2 HTAB C21 O4_$3 REM Highest difference peak 0.189, deepest hole -0.156, 1-sigma level 0.040 Q1 1 0.1146 0.4702 0.5771 11.00000 0.05 0.19 Q2 1 0.7657 0.5403 0.0578 11.00000 0.05 0.17 Q3 1 0.5198 0.4261 0.3290 11.00000 0.05 0.16 Q4 1 -0.2546 0.9636 0.9159 11.00000 0.05 0.16 Q5 1 0.1780 0.3408 0.5938 11.00000 0.05 0.16 Q6 1 0.5197 0.6213 0.3279 11.00000 0.05 0.15 Q7 1 0.4972 0.7129 0.2702 11.00000 0.05 0.15 Q8 1 0.6962 0.5846 0.1462 11.00000 0.05 0.15 Q9 1 0.1668 0.6359 0.5808 11.00000 0.05 0.15 Q10 1 0.3190 0.5714 0.2936 11.00000 0.05 0.14 ; _shelx_res_checksum 31355 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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 O O1 0.1477(3) 0.5424(5) 0.66816(11) 0.0476(7) Uani d 1 . . O O2 0.3072(3) 0.1188(5) 0.39878(10) 0.0407(6) Uani d 1 . . O O3 0.7195(4) 0.3955(11) 0.04333(15) 0.0967(14) Uani d 1 . . O O4 0.5966(4) 0.7477(8) 0.00909(14) 0.0786(10) Uani d 1 . . N N1 0.3611(4) 0.5542(5) 0.38830(13) 0.0369(7) Uani d 1 . . H H1 0.354(4) 0.724(8) 0.4011(17) 0.044 Uiso d 1 . . N N2 0.4173(3) 0.5102(5) 0.33080(12) 0.0359(7) Uani d 1 . . N N3 0.6379(4) 0.5860(10) 0.05105(16) 0.0632(11) Uani d 1 . . C C1 -0.1011(5) 0.8823(12) 0.93031(19) 0.0716(14) Uani d 1 . . H H1A -0.136189 1.063016 0.920871 0.086 Uiso calc 1 . . H H1B -0.010078 0.886972 0.961152 0.086 Uiso calc 1 . . H H1C -0.179652 0.782238 0.948641 0.086 Uiso calc 1 . . C C2 -0.0660(4) 0.7506(9) 0.86904(16) 0.0472(10) Uani d 1 . . C C3 0.0290(5) 0.5425(10) 0.86983(18) 0.0648(13) Uani d 1 . . H H3 0.074131 0.476727 0.909949 0.078 Uiso calc 1 . . C C4 0.0622(5) 0.4232(10) 0.81397(18) 0.0661(13) Uani d 1 . . H H4 0.130000 0.278228 0.816291 0.079 Uiso calc 1 . . C C5 -0.0019(4) 0.5115(8) 0.75470(16) 0.0401(8) Uani d 1 . . C C6 -0.0974(5) 0.7189(9) 0.75353(18) 0.0554(11) Uani d 1 . . H H6 -0.143298 0.783136 0.713380 0.067 Uiso calc 1 . . C C7 -0.1295(5) 0.8387(11) 0.80936(19) 0.0655(13) Uani d 1 . . H H7 -0.196585 0.984825 0.806939 0.079 Uiso calc 1 . . C C8 0.0349(4) 0.3846(8) 0.69368(16) 0.0462(9) Uani d 1 . . H H8A 0.072933 0.203070 0.702463 0.055 Uiso calc 1 . . H H8B -0.056490 0.374539 0.662284 0.055 Uiso calc 1 . . C C9 0.1823(4) 0.4840(7) 0.60809(15) 0.0360(8) Uani d 1 . . C C10 0.1222(4) 0.2735(7) 0.57052(15) 0.0387(9) Uani d 1 . . H H10 0.052049 0.156850 0.586470 0.046 Uiso calc 1 . . C C11 0.1652(4) 0.2362(7) 0.51033(15) 0.0382(8) Uani d 1 . . H H11 0.123802 0.092481 0.485007 0.046 Uiso calc 1 . . C C12 0.2679(4) 0.4034(6) 0.48530(15) 0.0311(8) Uani d 1 . . C C13 0.3289(4) 0.6103(7) 0.52395(15) 0.0388(8) Uani d 1 . . H H13 0.399403 0.727021 0.508241 0.047 Uiso calc 1 . . C C14 0.2876(4) 0.6465(7) 0.58475(16) 0.0419(9) Uani d 1 . . H H14 0.332136 0.785035 0.610979 0.050 Uiso calc 1 . . C C15 0.3126(4) 0.3454(7) 0.42105(15) 0.0318(8) Uani d 1 . . C C16 0.4317(4) 0.7143(7) 0.29601(16) 0.0410(8) Uani d 1 . . H H16 0.404496 0.884332 0.310034 0.049 Uiso calc 1 . . C C17 0.4910(4) 0.6807(7) 0.23383(16) 0.0405(9) Uani d 1 . . C C18 0.5876(5) 0.4754(8) 0.22322(18) 0.0463(9) Uani d 1 . . H H18 0.620600 0.356662 0.257043 0.056 Uiso calc 1 . . C C19 0.6358(5) 0.4437(9) 0.16319(18) 0.0509(10) Uani d 1 . . H H19 0.702781 0.304857 0.155381 0.061 Uiso calc 1 . . C C20 0.5843(4) 0.6185(9) 0.11485(17) 0.0491(10) Uani d 1 . . C C21 0.4894(5) 0.8217(8) 0.12357(17) 0.0545(11) Uani d 1 . . H H21 0.455193 0.937239 0.089234 0.065 Uiso calc 1 . . C C22 0.4445(5) 0.8546(8) 0.18362(17) 0.0526(10) Uani d 1 . . H H22 0.380496 0.998273 0.191162 0.063 Uiso calc 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 O1 0.0515(15) 0.0606(18) 0.0328(13) -0.0128(14) 0.0139(11) -0.0079(12) O2 0.0605(16) 0.0307(12) 0.0321(12) 0.0011(13) 0.0101(11) -0.0015(11) O3 0.076(2) 0.168(4) 0.0489(19) 0.040(3) 0.0199(16) -0.007(2) O4 0.113(3) 0.086(2) 0.0419(17) -0.015(2) 0.0324(17) 0.0032(17) N1 0.0571(18) 0.0288(16) 0.0259(14) 0.0000(15) 0.0105(12) -0.0017(12) N2 0.0492(17) 0.0322(15) 0.0274(15) 0.0007(14) 0.0087(12) -0.0020(12) N3 0.059(2) 0.094(3) 0.038(2) -0.011(2) 0.0142(17) -0.008(2) C1 0.065(3) 0.110(4) 0.043(2) -0.008(3) 0.023(2) -0.018(2) C2 0.0412(19) 0.068(3) 0.035(2) -0.014(2) 0.0156(15) -0.0043(19) C3 0.092(3) 0.069(3) 0.031(2) 0.011(3) -0.002(2) 0.0080(19) C4 0.083(3) 0.070(3) 0.044(2) 0.034(3) -0.001(2) 0.002(2) C5 0.0385(19) 0.049(2) 0.0337(18) -0.0054(19) 0.0090(15) -0.0003(16) C6 0.064(2) 0.065(3) 0.035(2) 0.015(2) -0.0024(18) 0.0006(19) C7 0.055(2) 0.094(4) 0.046(2) 0.025(3) 0.0002(19) -0.015(2) C8 0.048(2) 0.056(2) 0.037(2) -0.008(2) 0.0126(16) -0.0022(18) C9 0.0385(19) 0.042(2) 0.0282(17) 0.0001(17) 0.0049(14) -0.0003(15) C10 0.0410(19) 0.037(2) 0.0396(19) -0.0052(17) 0.0121(16) -0.0015(16) C11 0.0473(19) 0.0326(17) 0.0349(19) -0.0044(17) 0.0051(15) -0.0069(15) C12 0.0395(19) 0.0279(17) 0.0259(16) 0.0045(16) 0.0035(14) -0.0016(13) C13 0.0467(19) 0.039(2) 0.0311(17) -0.0066(18) 0.0073(15) -0.0001(16) C14 0.049(2) 0.043(2) 0.0333(19) -0.0072(19) 0.0019(15) -0.0074(16) C15 0.0373(19) 0.0297(18) 0.0276(16) 0.0041(16) 0.0006(14) -0.0006(14) C16 0.061(2) 0.0318(18) 0.0320(18) -0.0014(18) 0.0108(16) -0.0054(15) C17 0.056(2) 0.036(2) 0.0312(18) -0.0137(18) 0.0114(16) -0.0051(15) C18 0.054(2) 0.048(2) 0.038(2) -0.008(2) 0.0104(17) -0.0014(17) C19 0.051(2) 0.057(2) 0.047(2) -0.009(2) 0.0170(18) -0.010(2) C20 0.051(2) 0.068(3) 0.0306(19) -0.019(2) 0.0144(16) -0.007(2) C21 0.079(3) 0.054(3) 0.032(2) -0.018(2) 0.0133(19) 0.0022(18) C22 0.082(3) 0.040(2) 0.039(2) -0.006(2) 0.021(2) 0.0025(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 C9 O1 C8 . . 117.8(3) ? C15 N1 N2 . . 119.1(3) ? C15 N1 H1 . . 124(2) ? N2 N1 H1 . . 117(2) ? C16 N2 N1 . . 116.0(3) ? O4 N3 O3 . . 124.3(4) ? O4 N3 C20 . . 118.1(4) ? O3 N3 C20 . . 117.7(4) ? C2 C1 H1A . . 109.5 ? C2 C1 H1B . . 109.5 ? H1A C1 H1B . . 109.5 ? C2 C1 H1C . . 109.5 ? H1A C1 H1C . . 109.5 ? H1B C1 H1C . . 109.5 ? C3 C2 C7 . . 117.0(4) ? C3 C2 C1 . . 121.6(4) ? C7 C2 C1 . . 121.4(4) ? C2 C3 C4 . . 121.8(4) ? C2 C3 H3 . . 119.1 ? C4 C3 H3 . . 119.1 ? C3 C4 C5 . . 120.9(4) ? C3 C4 H4 . . 119.5 ? C5 C4 H4 . . 119.5 ? C6 C5 C4 . . 117.6(4) ? C6 C5 C8 . . 121.1(3) ? C4 C5 C8 . . 121.2(4) ? C5 C6 C7 . . 121.3(4) ? C5 C6 H6 . . 119.3 ? C7 C6 H6 . . 119.3 ? C6 C7 C2 . . 121.4(4) ? C6 C7 H7 . . 119.3 ? C2 C7 H7 . . 119.3 ? O1 C8 C5 . . 108.1(3) ? O1 C8 H8A . . 110.1 ? C5 C8 H8A . . 110.1 ? O1 C8 H8B . . 110.1 ? C5 C8 H8B . . 110.1 ? H8A C8 H8B . . 108.4 ? O1 C9 C14 . . 115.7(3) ? O1 C9 C10 . . 125.0(3) ? C14 C9 C10 . . 119.3(3) ? C11 C10 C9 . . 119.5(3) ? C11 C10 H10 . . 120.2 ? C9 C10 H10 . . 120.2 ? C10 C11 C12 . . 121.9(3) ? C10 C11 H11 . . 119.1 ? C12 C11 H11 . . 119.1 ? C11 C12 C13 . . 117.9(3) ? C11 C12 C15 . . 118.8(3) ? C13 C12 C15 . . 123.3(3) ? C14 C13 C12 . . 120.4(3) ? C14 C13 H13 . . 119.8 ? C12 C13 H13 . . 119.8 ? C13 C14 C9 . . 120.9(3) ? C13 C14 H14 . . 119.5 ? C9 C14 H14 . . 119.5 ? O2 C15 N1 . . 122.1(3) ? O2 C15 C12 . . 121.7(3) ? N1 C15 C12 . . 116.2(3) ? N2 C16 C17 . . 118.7(3) ? N2 C16 H16 . . 120.6 ? C17 C16 H16 . . 120.6 ? C18 C17 C22 . . 119.3(3) ? C18 C17 C16 . . 121.6(3) ? C22 C17 C16 . . 119.1(3) ? C19 C18 C17 . . 119.8(4) ? C19 C18 H18 . . 120.1 ? C17 C18 H18 . . 120.1 ? C20 C19 C18 . . 118.6(4) ? C20 C19 H19 . . 120.7 ? C18 C19 H19 . . 120.7 ? C21 C20 C19 . . 123.1(3) ? C21 C20 N3 . . 118.5(4) ? C19 C20 N3 . . 118.4(4) ? C20 C21 C22 . . 117.9(4) ? C20 C21 H21 . . 121.1 ? C22 C21 H21 . . 121.1 ? C21 C22 C17 . . 121.3(4) ? C21 C22 H22 . . 119.3 ? C17 C22 H22 . . 119.3 ? 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 O1 C9 . 1.363(4) ? O1 C8 . 1.437(4) ? O2 C15 . 1.237(4) ? O3 N3 . 1.231(6) ? O4 N3 . 1.227(5) ? N1 C15 . 1.358(4) ? N1 N2 . 1.376(4) ? N1 H1 . 0.90(4) ? N2 C16 . 1.279(4) ? N3 C20 . 1.480(5) ? C1 C2 . 1.511(5) ? C1 H1A . 0.9800 ? C1 H1B . 0.9800 ? C1 H1C . 0.9800 ? C2 C3 . 1.353(6) ? C2 C7 . 1.386(5) ? C3 C4 . 1.379(6) ? C3 H3 . 0.9500 ? C4 C5 . 1.381(5) ? C4 H4 . 0.9500 ? C5 C6 . 1.352(6) ? C5 C8 . 1.500(5) ? C6 C7 . 1.377(5) ? C6 H6 . 0.9500 ? C7 H7 . 0.9500 ? C8 H8A . 0.9900 ? C8 H8B . 0.9900 ? C9 C14 . 1.382(5) ? C9 C10 . 1.395(5) ? C10 C11 . 1.373(4) ? C10 H10 . 0.9500 ? C11 C12 . 1.395(5) ? C11 H11 . 0.9500 ? C12 C13 . 1.396(5) ? C12 C15 . 1.477(4) ? C13 C14 . 1.379(5) ? C13 H13 . 0.9500 ? C14 H14 . 0.9500 ? C16 C17 . 1.472(5) ? C16 H16 . 0.9500 ? C17 C18 . 1.385(5) ? C17 C22 . 1.398(5) ? C18 C19 . 1.385(5) ? C18 H18 . 0.9500 ? C19 C20 . 1.383(6) ? C19 H19 . 0.9500 ? C20 C21 . 1.360(6) ? C21 C22 . 1.374(5) ? C21 H21 . 0.9500 ? C22 H22 . 0.9500 ? 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 C14 H14 N2 2_656 0.95 2.68 3.524(5) 148.3 yes C16 H16 O2 1_565 0.95 2.45 3.259(4) 143.1 yes C21 H21 O4 2_655 0.95 2.59 3.532(5) 171.2 yes N1 H1 O2 1_565 0.90(4) 2.04(4) 2.911(4) 161(3) yes 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 C15 N1 N2 C16 . . . . 166.0(3) ? C7 C2 C3 C4 . . . . 0.3(7) ? C1 C2 C3 C4 . . . . -179.5(5) ? C2 C3 C4 C5 . . . . -0.5(8) ? C3 C4 C5 C6 . . . . 0.2(7) ? C3 C4 C5 C8 . . . . 179.3(4) ? C4 C5 C6 C7 . . . . 0.2(6) ? C8 C5 C6 C7 . . . . -178.9(4) ? C5 C6 C7 C2 . . . . -0.4(7) ? C3 C2 C7 C6 . . . . 0.2(7) ? C1 C2 C7 C6 . . . . 179.9(4) ? C9 O1 C8 C5 . . . . -170.9(3) ? C6 C5 C8 O1 . . . . 80.9(4) ? C4 C5 C8 O1 . . . . -98.2(5) ? C8 O1 C9 C14 . . . . 177.9(3) ? C8 O1 C9 C10 . . . . -3.5(5) ? O1 C9 C10 C11 . . . . 179.5(3) ? C14 C9 C10 C11 . . . . -2.0(5) ? C9 C10 C11 C12 . . . . 0.0(5) ? C10 C11 C12 C13 . . . . 1.1(5) ? C10 C11 C12 C15 . . . . 177.9(3) ? C11 C12 C13 C14 . . . . -0.2(5) ? C15 C12 C13 C14 . . . . -176.9(3) ? C12 C13 C14 C9 . . . . -1.8(5) ? O1 C9 C14 C13 . . . . -178.5(3) ? C10 C9 C14 C13 . . . . 2.9(5) ? N2 N1 C15 O2 . . . . -5.3(5) ? N2 N1 C15 C12 . . . . 174.1(3) ? C11 C12 C15 O2 . . . . -25.7(5) ? C13 C12 C15 O2 . . . . 151.0(3) ? C11 C12 C15 N1 . . . . 154.8(3) ? C13 C12 C15 N1 . . . . -28.5(5) ? N1 N2 C16 C17 . . . . -179.9(3) ? N2 C16 C17 C18 . . . . -27.8(5) ? N2 C16 C17 C22 . . . . 149.9(4) ? C22 C17 C18 C19 . . . . -0.4(5) ? C16 C17 C18 C19 . . . . 177.2(4) ? C17 C18 C19 C20 . . . . -0.6(5) ? C18 C19 C20 C21 . . . . 0.5(6) ? C18 C19 C20 N3 . . . . 179.1(4) ? O4 N3 C20 C21 . . . . 1.5(5) ? O3 N3 C20 C21 . . . . -177.5(4) ? O4 N3 C20 C19 . . . . -177.2(4) ? O3 N3 C20 C19 . . . . 3.9(5) ? C19 C20 C21 C22 . . . . 0.7(6) ? N3 C20 C21 C22 . . . . -177.9(3) ? C20 C21 C22 C17 . . . . -1.8(6) ? C18 C17 C22 C21 . . . . 1.7(6) ? C16 C17 C22 C21 . . . . -176.0(3) ? _cod_database_fobs_code 2022766