#------------------------------------------------------------------------------ #$Date: 2014-04-18 04:10:15 +0200 (Fri, 18 Apr 2014) $ #$Revision: 110027 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/23/7112340.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7112340 loop_ _publ_author_name 'do Pim, Walace D.' 'Oliveira, Willian X. C.' 'Ribeiro, Marcos A.' 'de Faria, \'Erica N.' 'Teixeira, Ivo F.' 'Stumpf, Humberto O.' 'Lago, Rochel M.' 'Pereira, Cynthia L. M.' 'Pinheiro, Carlos B.' 'Figueiredo-J\'unior, Jo\~ao C. D.' 'Nunes, Wallace C.' 'de Souza, Patterson P.' 'Pedroso, Emerson F.' 'Castellano, Mar\'ia' 'Cano, Joan' 'Julve, Miguel' _publ_section_title ; A pH-triggered bistable copper(ii) metallacycle as a reversible emulsion switch for biphasic processes ; _journal_issue 92 _journal_name_full 'Chemical Communications' _journal_page_first 10778 _journal_paper_doi 10.1039/c3cc46242k _journal_volume 49 _journal_year 2013 _chemical_formula_sum 'C44 H52 Cu2 N4 O16' _chemical_formula_weight 1019.98 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 68.274(2) _cell_angle_beta 86.530(2) _cell_angle_gamma 82.154(2) _cell_formula_units_Z 1 _cell_length_a 8.8221(2) _cell_length_b 11.5730(3) _cell_length_c 13.5452(3) _cell_measurement_reflns_used 18527 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 31.0505 _cell_measurement_theta_min 2.8184 _cell_volume 1272.60(6) _computing_cell_refinement '(Agilent Technologies, 2012)' _computing_data_collection '(Agilent Technologies, 2012)' _computing_data_reduction '(Agilent Technologies, 2012)' _computing_publication_material 'PublCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method 'w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_unetI/netI 0.0171 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 30924 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.83 _diffrn_standards_number 5199 _exptl_absorpt_coefficient_mu 0.903 _exptl_absorpt_correction_T_max 0.902 _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'light blue' _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 530 _exptl_crystal_size_max 0.5532 _exptl_crystal_size_mid 0.2403 _exptl_crystal_size_min 0.1168 _refine_diff_density_max 2.73 _refine_diff_density_min -1.821 _refine_diff_density_rms 0.183 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 314 _refine_ls_number_reflns 5199 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0759 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1623P)^2^+4.4737P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2447 _refine_ls_wR_factor_ref 0.2474 _reflns_number_gt 4891 _reflns_number_total 5199 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL cuedpba_2 CELL 0.71073 8.8221 11.5730 13.5452 68.274 86.530 82.154 ZERR 1.00 0.0002 0.0003 0.0003 0.002 0.002 0.002 LATT 1 SFAC C H N O CU UNIT 44 52 4 16 2 MERG 2 DFIX 1 H8a O8 DFIX -2 H8a H7a DFIX -2.2 H7a H8a DANG 2.2 0.01 H8A C23 EADP O8 C23 C24 SHEL 999 0.8 DFIX 0.800 0.001 O7 H7A FMAP 2 PLAN 15 ACTA BOND BOND $H L.S. 25 TEMP -153.00 WGHT 0.162500 4.446900 FVAR 5.45136 0.68457 CU1 5 0.363482 0.112783 0.011836 11.00000 0.01166 0.04243 = 0.01256 -0.00617 0.00070 -0.00789 O2 4 0.269185 -0.020483 0.129262 11.00000 0.01034 0.04056 = 0.01567 -0.00721 -0.00011 -0.00532 O4 4 0.568731 0.036435 0.069359 11.00000 0.01289 0.04604 = 0.01547 -0.01287 0.00187 -0.00773 O1 4 0.153199 0.177222 -0.032587 11.00000 0.01598 0.04350 = 0.01619 -0.00262 -0.00204 -0.00890 O6 4 0.713009 -0.026920 0.214461 11.00000 0.01311 0.04980 = 0.01780 -0.01280 0.00016 -0.00039 O5 4 0.389573 0.193400 0.150943 11.00000 0.02134 0.04085 = 0.01769 -0.00711 -0.00414 -0.00050 N1 3 0.030682 -0.064996 0.192269 11.00000 0.00994 0.03284 = 0.01657 -0.00663 -0.00119 -0.00363 AFIX 43 H1 2 -0.067877 -0.039111 0.183828 11.00000 -1.20000 AFIX 0 O3 4 -0.084705 0.131571 0.021283 11.00000 0.01271 0.04610 = 0.02618 -0.00158 -0.00445 -0.00449 N2 3 0.505958 0.085744 0.309924 11.00000 0.01622 0.03264 = 0.01470 -0.00867 -0.00214 0.00049 AFIX 43 H2 2 0.579834 0.026178 0.341269 11.00000 -1.20000 AFIX 0 C2 1 0.125988 0.001091 0.123046 11.00000 0.01448 0.03506 = 0.01461 -0.00969 -0.00043 -0.00492 C17 1 0.487157 0.115260 0.205595 11.00000 0.01401 0.03335 = 0.01479 -0.00791 0.00111 -0.00775 C3 1 0.077828 -0.176920 0.280846 11.00000 0.01160 0.02990 = 0.01670 -0.00895 0.00225 -0.00387 C4 1 0.150333 -0.171398 0.367982 11.00000 0.01497 0.02687 = 0.01777 -0.00967 0.00138 -0.00449 C16 1 0.415964 0.143079 0.373929 11.00000 0.01619 0.02747 = 0.01607 -0.00754 -0.00480 0.00001 C11 1 0.313725 0.075458 0.449063 11.00000 0.01649 0.02397 = 0.01543 -0.00628 -0.00516 -0.00017 C9 1 0.177791 -0.045571 0.369959 11.00000 0.01877 0.02380 = 0.01865 -0.00669 -0.00308 -0.00384 AFIX 23 H9A 2 0.078012 0.000563 0.378741 11.00000 -1.20000 H9B 2 0.221585 0.003737 0.300432 11.00000 -1.20000 AFIX 0 C18 1 0.602253 0.033453 0.160122 11.00000 0.01076 0.03769 = 0.01478 -0.00817 0.00299 -0.00813 C8 1 0.045508 -0.289458 0.277827 11.00000 0.01964 0.03420 = 0.02616 -0.01677 0.00021 -0.00360 AFIX 43 H8 2 -0.004232 -0.290749 0.218035 11.00000 -1.20000 AFIX 0 C10 1 0.284675 -0.053681 0.457878 11.00000 0.02265 0.02544 = 0.01808 -0.00886 -0.00317 -0.00363 AFIX 23 H10A 2 0.238083 -0.096727 0.528124 11.00000 -1.20000 H10B 2 0.383073 -0.103641 0.452431 11.00000 -1.20000 AFIX 0 C15 1 0.436029 0.264015 0.363427 11.00000 0.02216 0.02771 = 0.02293 -0.00460 -0.00092 -0.00377 AFIX 43 H15 2 0.503986 0.309348 0.310616 11.00000 -1.20000 AFIX 0 C5 1 0.190859 -0.283947 0.450655 11.00000 0.02334 0.02806 = 0.02117 -0.00994 -0.00379 -0.00070 AFIX 43 H5 2 0.241725 -0.283567 0.510360 11.00000 -1.20000 AFIX 0 C1 1 0.054773 0.114076 0.028970 11.00000 0.01582 0.03798 = 0.01570 -0.00634 -0.00241 -0.00507 C12 1 0.235217 0.131825 0.515532 11.00000 0.01998 0.03030 = 0.02162 -0.01016 0.00234 -0.00175 AFIX 43 H12 2 0.165775 0.087448 0.567645 11.00000 -1.20000 AFIX 0 C13 1 0.257542 0.252693 0.506337 11.00000 0.02677 0.03114 = 0.03060 -0.01601 0.00423 0.00073 AFIX 43 H13 2 0.204375 0.289573 0.552594 11.00000 -1.20000 AFIX 0 C14 1 0.357189 0.318648 0.429771 11.00000 0.03200 0.02402 = 0.03682 -0.01179 0.00127 -0.00355 AFIX 43 H14 2 0.371411 0.401229 0.422794 11.00000 -1.20000 AFIX 0 C6 1 0.159301 -0.396596 0.448584 11.00000 0.03377 0.02204 = 0.02832 -0.00646 -0.00440 0.00161 AFIX 43 H6 2 0.188111 -0.472096 0.506731 11.00000 -1.20000 AFIX 0 C7 1 0.086337 -0.400570 0.362891 11.00000 0.03252 0.02806 = 0.03578 -0.01723 -0.00008 -0.00551 AFIX 43 H7 2 0.064204 -0.478206 0.361923 11.00000 -1.20000 AFIX 0 O7 4 0.441334 0.253714 -0.100767 11.00000 0.02021 0.04275 = 0.01838 -0.00189 -0.00078 -0.00987 PART 1 C21A 1 0.437762 0.269042 -0.210674 21.00000 0.03375 0.03566 = 0.01912 -0.00283 0.00428 -0.00610 AFIX 23 H21A 2 0.344809 0.238125 -0.224121 21.00000 -1.20000 H21B 2 0.528161 0.218782 -0.227900 21.00000 -1.20000 AFIX 0 C22A 1 0.437777 0.402558 -0.279637 21.00000 0.07680 0.04414 = 0.03107 0.00863 -0.01284 -0.02273 AFIX 137 H22A 2 0.445429 0.410280 -0.354247 21.00000 -1.50000 H22B 2 0.525279 0.434994 -0.262116 21.00000 -1.50000 H22C 2 0.342633 0.450783 -0.268199 21.00000 -1.50000 AFIX 0 PART 2 C21B 1 0.379167 0.337113 -0.204947 -21.00000 0.03106 0.06023 = 0.03985 0.01961 -0.01467 -0.01222 AFIX 23 H21C 2 0.277467 0.314006 -0.211953 -21.00000 -1.20000 H21D 2 0.363362 0.423914 -0.206007 -21.00000 -1.20000 AFIX 0 C22B 1 0.461801 0.336291 -0.287666 -21.00000 0.10996 0.09391 = 0.02755 -0.00214 -0.01227 -0.04262 AFIX 137 H22D 2 0.448989 0.420045 -0.343355 -21.00000 -1.50000 H22E 2 0.428898 0.275737 -0.314271 -21.00000 -1.50000 H22F 2 0.569734 0.312471 -0.267656 -21.00000 -1.50000 AFIX 0 PART -1 O8 4 0.694646 0.321861 -0.067352 11.00000 0.04991 0.05957 = 0.16776 -0.02974 -0.03308 -0.00250 PART 0 C24 1 0.773417 0.562377 -0.147896 11.00000 0.04991 0.05957 = 0.16776 -0.02974 -0.03308 -0.00250 AFIX 137 H24A 2 0.752252 0.580094 -0.222630 11.00000 -1.50000 H24C 2 0.883904 0.556241 -0.138583 11.00000 -1.50000 H24B 2 0.720913 0.630175 -0.126948 11.00000 -1.50000 AFIX 0 C23 1 0.715108 0.436656 -0.077461 11.00000 0.04991 0.05957 = 0.16776 -0.02974 -0.03308 -0.00250 AFIX 23 H23B 2 0.772219 0.418107 -0.011547 11.00000 -1.20000 H23A 2 0.610059 0.468067 -0.061450 11.00000 -1.20000 AFIX 0 H7A 2 0.492821 0.290465 -0.078693 11.00000 -1.20000 H8A 2 0.741310 0.253738 -0.094515 11.00000 -1.20000 HKLF 4 REM cuedpba_2 REM R1 = 0.0759 for 4891 Fo > 4sig(Fo) and 0.0783 for all 5199 data REM 314 parameters refined using 4 restraints END WGHT 0.1622 4.4705 REM Highest difference peak 2.730, deepest hole -1.820, 1-sigma level 0.183 Q1 1 1.0074 0.6772 -0.2499 11.00000 0.05 2.73 Q2 1 0.7142 0.3351 0.1695 11.00000 0.05 2.61 Q3 1 1.0471 0.7378 -0.2085 11.00000 0.05 1.79 ; _[local]_cod_data_source_file c3cc46242k.txt _[local]_cod_data_source_block cuedpba2 _cod_original_cell_volume 1272.60(5) _cod_database_code 7112340 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.36348(5) 0.11278(5) 0.01184(4) 0.0229(2) Uani 1 1 d . . . O2 O 0.2692(3) -0.0205(3) 0.1293(2) 0.0229(6) Uani 1 1 d . . . O4 O 0.5687(3) 0.0364(3) 0.0694(2) 0.0240(6) Uani 1 1 d . . . O1 O 0.1532(4) 0.1772(3) -0.0326(2) 0.0270(7) Uani 1 1 d . . . O6 O 0.7130(3) -0.0269(3) 0.2145(2) 0.0271(7) Uani 1 1 d . . . O5 O 0.3896(4) 0.1934(3) 0.1509(2) 0.0278(7) Uani 1 1 d . . . N1 N 0.0307(4) -0.0650(3) 0.1923(3) 0.0203(7) Uani 1 1 d . . . H1 H -0.0679 -0.0391 0.1838 0.024 Uiso 1 1 calc R . . O3 O -0.0847(4) 0.1316(3) 0.0213(3) 0.0314(8) Uani 1 1 d . . . N2 N 0.5060(4) 0.0857(3) 0.3099(3) 0.0214(7) Uani 1 1 d . . . H2 H 0.5798 0.0262 0.3413 0.026 Uiso 1 1 calc R . . C2 C 0.1260(5) 0.0011(4) 0.1230(3) 0.0210(8) Uani 1 1 d . . . C17 C 0.4872(4) 0.1153(4) 0.2056(3) 0.0206(8) Uani 1 1 d . . . C3 C 0.0778(4) -0.1769(4) 0.2808(3) 0.0193(8) Uani 1 1 d . . . C4 C 0.1503(4) -0.1714(4) 0.3680(3) 0.0193(8) Uani 1 1 d . . . C16 C 0.4160(5) 0.1431(4) 0.3739(3) 0.0201(8) Uani 1 1 d . . . C11 C 0.3137(5) 0.0755(4) 0.4491(3) 0.0189(8) Uani 1 1 d . . . C9 C 0.1778(5) -0.0456(4) 0.3700(3) 0.0205(8) Uani 1 1 d . . . H9A H 0.0780 0.0006 0.3787 0.025 Uiso 1 1 calc R . . H9B H 0.2216 0.0037 0.3004 0.025 Uiso 1 1 calc R . . C18 C 0.6023(4) 0.0335(4) 0.1601(3) 0.0211(8) Uani 1 1 d . . . C8 C 0.0455(5) -0.2895(4) 0.2778(4) 0.0250(9) Uani 1 1 d . . . H8 H -0.0042 -0.2907 0.2180 0.030 Uiso 1 1 calc R . . C10 C 0.2847(5) -0.0537(4) 0.4579(3) 0.0216(8) Uani 1 1 d . . . H10A H 0.2381 -0.0967 0.5281 0.026 Uiso 1 1 calc R . . H10B H 0.3831 -0.1036 0.4524 0.026 Uiso 1 1 calc R . . C15 C 0.4360(5) 0.2640(4) 0.3634(4) 0.0255(9) Uani 1 1 d . . . H15 H 0.5040 0.3093 0.3106 0.031 Uiso 1 1 calc R . . C5 C 0.1909(5) -0.2839(4) 0.4507(3) 0.0240(9) Uani 1 1 d . . . H5 H 0.2417 -0.2836 0.5104 0.029 Uiso 1 1 calc R . . C1 C 0.0548(5) 0.1141(4) 0.0290(3) 0.0239(9) Uani 1 1 d . . . C12 C 0.2352(5) 0.1318(4) 0.5155(3) 0.0240(9) Uani 1 1 d . . . H12 H 0.1658 0.0874 0.5676 0.029 Uiso 1 1 calc R . . C13 C 0.2575(5) 0.2527(4) 0.5063(4) 0.0288(10) Uani 1 1 d . . . H13 H 0.2044 0.2896 0.5526 0.035 Uiso 1 1 calc R . . C14 C 0.3572(6) 0.3186(4) 0.4298(4) 0.0308(10) Uani 1 1 d . . . H14 H 0.3714 0.4012 0.4228 0.037 Uiso 1 1 calc R . . C6 C 0.1593(6) -0.3966(4) 0.4486(4) 0.0292(10) Uani 1 1 d . . . H6 H 0.1881 -0.4721 0.5067 0.035 Uiso 1 1 calc R . . C7 C 0.0863(6) -0.4006(4) 0.3629(4) 0.0304(10) Uani 1 1 d . . . H7 H 0.0642 -0.4782 0.3619 0.036 Uiso 1 1 calc R . . O7 O 0.4413(4) 0.2537(3) -0.1008(3) 0.0292(7) Uani 1 1 d D . . C21A C 0.4378(12) 0.2690(10) -0.2107(6) 0.032(3) Uani 0.68(3) 1 d P A 1 H21A H 0.3448 0.2381 -0.2241 0.038 Uiso 0.68(3) 1 calc PR A 1 H21B H 0.5282 0.2188 -0.2279 0.038 Uiso 0.68(3) 1 calc PR A 1 C22A C 0.4378(16) 0.4026(13) -0.2796(10) 0.055(3) Uani 0.68(3) 1 d P A 1 H22A H 0.4454 0.4103 -0.3542 0.083 Uiso 0.68(3) 1 calc PR A 1 H22B H 0.5253 0.4350 -0.2621 0.083 Uiso 0.68(3) 1 calc PR A 1 H22C H 0.3426 0.4508 -0.2682 0.083 Uiso 0.68(3) 1 calc PR A 1 C21B C 0.379(3) 0.337(3) -0.2049(18) 0.053(9) Uani 0.32(3) 1 d P A 2 H21C H 0.2775 0.3140 -0.2120 0.064 Uiso 0.32(3) 1 calc PR A 2 H21D H 0.3634 0.4239 -0.2060 0.064 Uiso 0.32(3) 1 calc PR A 2 C22B C 0.462(5) 0.336(5) -0.288(2) 0.079(12) Uani 0.32(3) 1 d P A 2 H22D H 0.4490 0.4200 -0.3434 0.119 Uiso 0.32(3) 1 calc PR A 2 H22E H 0.4289 0.2757 -0.3143 0.119 Uiso 0.32(3) 1 calc PR A 2 H22F H 0.5697 0.3125 -0.2677 0.119 Uiso 0.32(3) 1 calc PR A 2 O8 O 0.6946(7) 0.3219(6) -0.0674(7) 0.0949(18) Uani 1 1 d D B -1 C24 C 0.7734(10) 0.5624(8) -0.1479(11) 0.0949(18) Uani 1 1 d . B . H24A H 0.7523 0.5801 -0.2226 0.142 Uiso 1 1 calc R . . H24C H 0.8839 0.5562 -0.1386 0.142 Uiso 1 1 calc R . . H24B H 0.7209 0.6302 -0.1269 0.142 Uiso 1 1 calc R . . C23 C 0.7151(10) 0.4367(8) -0.0775(11) 0.0949(18) Uani 1 1 d D . . H23B H 0.7722 0.4181 -0.0115 0.114 Uiso 1 1 calc R B . H23A H 0.6101 0.4681 -0.0615 0.114 Uiso 1 1 calc R . . H7A H 0.493(7) 0.290(9) -0.079(9) 0.114 Uiso 1 1 d D . . H8A H 0.741(8) 0.254(4) -0.095(7) 0.114 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0117(3) 0.0424(4) 0.0126(3) -0.0062(2) 0.0007(2) -0.0079(2) O2 0.0103(13) 0.0406(17) 0.0157(14) -0.0072(12) -0.0001(10) -0.0053(12) O4 0.0129(14) 0.0460(18) 0.0155(14) -0.0129(13) 0.0019(11) -0.0077(12) O1 0.0160(14) 0.0435(18) 0.0162(14) -0.0026(13) -0.0020(11) -0.0089(13) O6 0.0131(14) 0.0498(19) 0.0178(15) -0.0128(13) 0.0002(11) -0.0004(13) O5 0.0213(15) 0.0409(18) 0.0177(15) -0.0071(13) -0.0041(12) -0.0005(13) N1 0.0099(15) 0.0328(18) 0.0166(16) -0.0066(14) -0.0012(12) -0.0036(13) O3 0.0127(15) 0.0461(19) 0.0262(17) -0.0016(14) -0.0044(12) -0.0045(13) N2 0.0162(16) 0.0326(18) 0.0147(16) -0.0087(14) -0.0021(13) 0.0005(13) C2 0.0145(18) 0.035(2) 0.0146(18) -0.0097(16) -0.0004(14) -0.0049(16) C17 0.0140(18) 0.033(2) 0.0148(18) -0.0079(16) 0.0011(14) -0.0077(16) C3 0.0116(17) 0.030(2) 0.0167(19) -0.0090(16) 0.0022(14) -0.0039(14) C4 0.0150(18) 0.027(2) 0.0178(19) -0.0097(16) 0.0014(15) -0.0045(15) C16 0.0162(18) 0.027(2) 0.0161(19) -0.0075(15) -0.0048(15) 0.0000(15) C11 0.0165(18) 0.0240(19) 0.0154(18) -0.0063(15) -0.0052(14) -0.0002(14) C9 0.0188(19) 0.0238(19) 0.0186(19) -0.0067(15) -0.0031(15) -0.0038(15) C18 0.0108(18) 0.038(2) 0.0148(18) -0.0082(16) 0.0030(14) -0.0081(16) C8 0.020(2) 0.034(2) 0.026(2) -0.0168(18) 0.0002(16) -0.0036(16) C10 0.023(2) 0.025(2) 0.0181(19) -0.0089(15) -0.0032(16) -0.0036(15) C15 0.022(2) 0.028(2) 0.023(2) -0.0046(17) -0.0009(16) -0.0038(16) C5 0.023(2) 0.028(2) 0.021(2) -0.0099(17) -0.0038(16) -0.0007(16) C1 0.016(2) 0.038(2) 0.0157(19) -0.0063(17) -0.0024(15) -0.0051(17) C12 0.020(2) 0.030(2) 0.022(2) -0.0102(17) 0.0023(16) -0.0018(16) C13 0.027(2) 0.031(2) 0.031(2) -0.0160(19) 0.0042(18) 0.0007(18) C14 0.032(2) 0.024(2) 0.037(3) -0.0118(19) 0.001(2) -0.0036(18) C6 0.034(2) 0.022(2) 0.028(2) -0.0065(17) -0.0044(19) 0.0016(18) C7 0.033(2) 0.028(2) 0.036(3) -0.0172(19) 0.000(2) -0.0055(18) O7 0.0202(15) 0.0428(18) 0.0184(16) -0.0019(13) -0.0008(12) -0.0099(13) C21A 0.034(5) 0.036(5) 0.019(4) -0.003(3) 0.004(3) -0.006(4) C22A 0.077(8) 0.044(6) 0.031(5) 0.009(5) -0.013(5) -0.023(6) C21B 0.031(11) 0.060(17) 0.040(11) 0.020(11) -0.015(9) -0.012(12) C22B 0.11(3) 0.09(3) 0.028(13) -0.002(16) -0.012(13) -0.04(2) O8 0.050(2) 0.060(2) 0.168(5) -0.030(3) -0.033(3) -0.0025(18) C24 0.050(2) 0.060(2) 0.168(5) -0.030(3) -0.033(3) -0.0025(18) C23 0.050(2) 0.060(2) 0.168(5) -0.030(3) -0.033(3) -0.0025(18) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 O1 Cu1 O7 91.83(14) . . O1 Cu1 O4 174.58(12) . . O7 Cu1 O4 93.45(13) . . O1 Cu1 O2 84.43(13) . . O7 Cu1 O2 174.90(13) . . O4 Cu1 O2 90.22(13) . . O1 Cu1 O4 103.25(13) . 2_655 O7 Cu1 O4 96.82(13) . 2_655 O4 Cu1 O4 77.34(13) . 2_655 O2 Cu1 O4 87.44(12) . 2_655 O1 Cu1 O5 102.05(13) . . O7 Cu1 O5 94.70(13) . . O4 Cu1 O5 76.30(12) . . O2 Cu1 O5 82.72(12) . . O4 Cu1 O5 151.76(11) 2_655 . C2 O2 Cu1 109.8(3) . . C18 O4 Cu1 119.1(3) . . C18 O4 Cu1 130.2(3) . 2_655 Cu1 O4 Cu1 102.65(13) . 2_655 C1 O1 Cu1 113.6(3) . . C17 O5 Cu1 101.0(3) . . C2 N1 C3 123.8(3) . . C2 N1 H1 118.1 . . C3 N1 H1 118.1 . . C17 N2 C16 125.2(4) . . C17 N2 H2 117.4 . . C16 N2 H2 117.4 . . O2 C2 N1 124.7(4) . . O2 C2 C1 118.5(4) . . N1 C2 C1 116.7(4) . . O5 C17 N2 125.8(4) . . O5 C17 C18 122.0(4) . . N2 C17 C18 112.2(4) . . C8 C3 C4 121.7(4) . . C8 C3 N1 117.4(4) . . C4 C3 N1 120.8(4) . . C5 C4 C3 117.0(4) . . C5 C4 C9 123.0(4) . . C3 C4 C9 120.0(4) . . C15 C16 C11 121.2(4) . . C15 C16 N2 119.1(4) . . C11 C16 N2 119.7(4) . . C12 C11 C16 118.0(4) . . C12 C11 C10 120.1(4) . . C16 C11 C10 121.8(4) . . C4 C9 C10 114.6(3) . . C4 C9 H9A 108.6 . . C10 C9 H9A 108.6 . . C4 C9 H9B 108.6 . . C10 C9 H9B 108.6 . . H9A C9 H9B 107.6 . . O6 C18 O4 127.3(4) . . O6 C18 C17 117.8(4) . . O4 C18 C17 114.8(4) . . C3 C8 C7 119.6(4) . . C3 C8 H8 120.2 . . C7 C8 H8 120.2 . . C11 C10 C9 110.8(3) . . C11 C10 H10A 109.5 . . C9 C10 H10A 109.5 . . C11 C10 H10B 109.5 . . C9 C10 H10B 109.5 . . H10A C10 H10B 108.1 . . C14 C15 C16 120.1(4) . . C14 C15 H15 119.9 . . C16 C15 H15 119.9 . . C6 C5 C4 121.8(4) . . C6 C5 H5 119.1 . . C4 C5 H5 119.1 . . O3 C1 O1 128.4(4) . . O3 C1 C2 118.1(4) . . O1 C1 C2 113.5(4) . . C11 C12 C13 120.8(4) . . C11 C12 H12 119.6 . . C13 C12 H12 119.6 . . C14 C13 C12 120.0(4) . . C14 C13 H13 120.0 . . C12 C13 H13 120.0 . . C15 C14 C13 119.9(4) . . C15 C14 H14 120.1 . . C13 C14 H14 120.1 . . C7 C6 C5 120.6(4) . . C7 C6 H6 119.7 . . C5 C6 H6 119.7 . . C6 C7 C8 119.2(4) . . C6 C7 H7 120.4 . . C8 C7 H7 120.4 . . C21A O7 C21B 36.4(14) . . C21A O7 Cu1 122.2(4) . . C21B O7 Cu1 131.9(8) . . C21A O7 H7A 123(8) . . C21B O7 H7A 110(9) . . Cu1 O7 H7A 113(8) . . O7 C21A C22A 110.6(10) . . O7 C21A H21A 109.5 . . C22A C21A H21A 109.5 . . O7 C21A H21B 109.5 . . C22A C21A H21B 109.5 . . H21A C21A H21B 108.1 . . C22B C21B O7 116(3) . . C22B C21B H21C 108.2 . . O7 C21B H21C 108.2 . . C22B C21B H21D 108.2 . . O7 C21B H21D 108.2 . . H21C C21B H21D 107.4 . . C21B C22B H22D 109.5 . . C21B C22B H22E 109.5 . . H22D C22B H22E 109.5 . . C21B C22B H22F 109.5 . . H22D C22B H22F 109.5 . . H22E C22B H22F 109.5 . . C23 O8 H8A 139(3) . . C23 C24 H24A 109.5 . . C23 C24 H24C 109.5 . . H24A C24 H24C 109.5 . . C23 C24 H24B 109.5 . . H24A C24 H24B 109.5 . . H24C C24 H24B 109.5 . . O8 C23 C24 147.5(13) . . O8 C23 H23B 99.9 . . C24 C23 H23B 99.9 . . O8 C23 H23A 99.9 . . C24 C23 H23A 99.9 . . H23B C23 H23A 104.2 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cu1 O1 1.945(3) . Cu1 O7 1.948(3) . Cu1 O4 1.973(3) . Cu1 O2 1.994(3) . Cu1 O4 2.365(3) 2_655 Cu1 O5 2.426(3) . O2 C2 1.256(5) . O4 C18 1.269(5) . O4 Cu1 2.365(3) 2_655 O1 C1 1.272(5) . O6 C18 1.227(5) . O5 C17 1.215(5) . N1 C2 1.312(6) . N1 C3 1.433(5) . N1 H1 0.8800 . O3 C1 1.224(5) . N2 C17 1.340(5) . N2 C16 1.422(5) . N2 H2 0.8800 . C2 C1 1.539(6) . C17 C18 1.549(6) . C3 C8 1.386(6) . C3 C4 1.402(6) . C4 C5 1.386(6) . C4 C9 1.519(5) . C16 C15 1.388(6) . C16 C11 1.398(6) . C11 C12 1.397(6) . C11 C10 1.511(6) . C9 C10 1.531(5) . C9 H9A 0.9900 . C9 H9B 0.9900 . C8 C7 1.392(7) . C8 H8 0.9500 . C10 H10A 0.9900 . C10 H10B 0.9900 . C15 C14 1.384(7) . C15 H15 0.9500 . C5 C6 1.380(6) . C5 H5 0.9500 . C12 C13 1.398(6) . C12 H12 0.9500 . C13 C14 1.385(7) . C13 H13 0.9500 . C14 H14 0.9500 . C6 C7 1.379(7) . C6 H6 0.9500 . C7 H7 0.9500 . O7 C21A 1.434(8) . O7 C21B 1.471(18) . O7 H7A 0.8000(10) . C21A C22A 1.480(17) . C21A H21A 0.9900 . C21A H21B 0.9900 . C22A H22A 0.9800 . C22A H22B 0.9800 . C22A H22C 0.9800 . C21B C22B 1.30(5) . C21B H21C 0.9900 . C21B H21D 0.9900 . C22B H22D 0.9800 . C22B H22E 0.9800 . C22B H22F 0.9800 . O8 C23 1.321(10) . O8 H8A 1.017(18) . C24 C23 1.552(13) . C24 H24A 0.9800 . C24 H24C 0.9800 . C24 H24B 0.9800 . C23 H23B 0.9900 . C23 H23A 0.9900 .