#------------------------------------------------------------------------------ #$Date: 2014-04-23 10:14:20 +0100 (Wed, 23 Apr 2014) $ #$Revision: 111478 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/23/7112342.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_7112342 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, Jr, 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 (Cambridge, England)' _journal_page_first 10778 _journal_page_last 10780 _journal_paper_doi 10.1039/c3cc46242k _journal_volume 49 _journal_year 2013 _chemical_absolute_configuration ad _chemical_formula_moiety 'C36 H24 Cu2 N4 O12, 4(C16 H35 N), 4(O)' _chemical_formula_sum 'C100 H164 Cu2 N8 O16' _chemical_formula_weight 1861.47 _space_group_IT_number 23 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'I 2 2' _symmetry_space_group_name_H-M 'I 2 2 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_creation_date 2012-07-11T21:57:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 14.2234(2) _cell_length_b 17.5944(4) _cell_length_c 21.3698(4) _cell_measurement_reflns_used 22533 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.5331 _cell_measurement_theta_min 1.8374 _cell_volume 5347.84(17) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'publcif (Westrip, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SUPERFLIP (Palatinus, 2007)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.4186 _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_orient_matrix_UB_11 0.0359037 _diffrn_orient_matrix_UB_12 0.0134459 _diffrn_orient_matrix_UB_13 0.0202 _diffrn_orient_matrix_UB_21 -0.0248184 _diffrn_orient_matrix_UB_22 -0.0146427 _diffrn_orient_matrix_UB_23 0.0261547 _diffrn_orient_matrix_UB_31 0.0241179 _diffrn_orient_matrix_UB_32 -0.0350636 _diffrn_orient_matrix_UB_33 -0.0031669 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_unetI/netI 0.0195 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 55826 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 1.84 _exptl_absorpt_coefficient_mu 0.46 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_correction_T_min 0.929 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'light blue' _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prismatic _exptl_crystal_F_000 2076 _exptl_crystal_size_max 0.4166 _exptl_crystal_size_mid 0.3933 _exptl_crystal_size_min 0.3814 _refine_diff_density_max 1.295 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.101 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.012(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 5497 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.167 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0490 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1781P)^2^+5.8980P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1443 _refine_ls_wR_factor_ref 0.1500 _reflns_number_gt 5208 _reflns_number_total 5497 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL Cued_Bu4N CELL 0.71073 14.2234 17.5944 21.3698 90.000 90.000 90.000 ZERR 2.00 0.0002 0.0004 0.0004 0.000 0.000 0.000 LATT -2 SYMM - X, - Y, Z SYMM - X, Y, - Z SYMM X, - Y, - Z SFAC C H N O CU UNIT 200 328 16 32 4 MERG 2 SHEL 50 0.8 FMAP 2 PLAN 20 ACTA BOND $H HTAB LIST 3 L.S. 50 TEMP 20 WGHT 0.099400 3.141100 FVAR 1.82404 0.50000 CU1 5 1.000000 0.812722 1.000000 10.50000 0.01342 0.03835 = 0.02384 0.00000 -0.00065 0.00000 O1 4 1.054176 0.795659 0.917451 11.00000 0.01885 0.05343 = 0.02744 -0.00466 0.00096 0.00832 N1 3 0.885729 0.833482 0.953561 11.00000 0.01536 0.02954 = 0.02693 -0.00615 -0.00269 0.00206 O2 4 1.017131 0.806772 0.816709 11.00000 0.03088 0.06115 = 0.02782 -0.00993 0.00322 0.00688 O3 4 0.839263 0.854392 0.852426 11.00000 0.03172 0.08445 = 0.02766 -0.00995 -0.00563 0.02032 N2 3 0.285755 0.695533 0.820251 11.00000 0.02259 0.04196 = 0.03336 -0.01209 0.00405 0.00231 C2 1 0.896880 0.835154 0.892536 11.00000 0.02099 0.03933 = 0.02749 -0.00926 -0.00413 0.00694 C3 1 0.796381 0.851956 0.979635 11.00000 0.01547 0.04408 = 0.02232 -0.00449 -0.00238 0.00414 C4 1 0.718864 0.806362 0.966218 11.00000 0.02132 0.03675 = 0.03016 -0.00045 -0.00079 0.00110 AFIX 43 H4A 2 0.725305 0.765698 0.938746 11.00000 -1.20000 AFIX 0 C22 1 0.388868 0.672312 0.815340 11.00000 0.02040 0.04760 = 0.03339 -0.00662 0.00431 0.00419 AFIX 23 H22A 2 0.395577 0.621157 0.831667 11.00000 -1.20000 H22B 2 0.406301 0.671057 0.771469 11.00000 -1.20000 AFIX 0 C1 1 0.997952 0.810560 0.872597 11.00000 0.02222 0.03831 = 0.02450 -0.00847 0.00091 0.00289 C8 1 0.785775 0.914301 1.019726 11.00000 0.02115 0.04994 = 0.03088 -0.01479 -0.00277 0.00464 C6 1 0.622064 0.880413 1.035218 11.00000 0.02110 0.06788 = 0.03703 0.00104 0.00587 0.00689 AFIX 43 H6A 2 0.564671 0.889300 1.054743 11.00000 -1.20000 AFIX 0 C7 1 0.699080 0.926703 1.047627 11.00000 0.02657 0.06222 = 0.03885 -0.01846 0.00202 0.01009 AFIX 43 H7A 2 0.692276 0.967051 1.075373 11.00000 -1.20000 AFIX 0 C13 1 0.271003 0.776564 0.799608 11.00000 0.02815 0.03904 = 0.05527 -0.01692 -0.00455 0.00108 AFIX 23 H13A 2 0.204414 0.788096 0.802033 11.00000 -1.20000 H13B 2 0.303271 0.809881 0.828706 11.00000 -1.20000 AFIX 0 C5 1 0.632075 0.821018 0.993448 11.00000 0.01568 0.05531 = 0.03873 0.00152 0.00039 -0.00221 AFIX 43 H5A 2 0.580560 0.790772 0.983541 11.00000 -1.20000 AFIX 0 C18 1 0.251069 0.691067 0.887284 11.00000 0.02845 0.07187 = 0.03509 -0.02037 0.00711 -0.00343 AFIX 23 H18A 2 0.184216 0.701946 0.887720 11.00000 -1.20000 H18B 2 0.282159 0.730385 0.911455 11.00000 -1.20000 AFIX 0 C16 1 0.080114 0.586873 0.738898 11.00000 0.02432 0.04487 = 0.05338 -0.00564 0.00185 -0.00394 AFIX 23 H16A 2 0.093547 0.539884 0.760890 11.00000 -1.20000 H16B 2 0.012609 0.594571 0.740104 11.00000 -1.20000 AFIX 0 C14 1 0.232269 0.640562 0.777784 11.00000 0.02722 0.03504 = 0.03360 -0.01521 0.00414 -0.00203 AFIX 43 H14A 2 0.262562 0.602190 0.755664 11.00000 -1.20000 AFIX 0 C9 1 0.863935 0.971398 1.027749 11.00000 0.02174 0.05677 = 0.04852 -0.03019 -0.00421 0.00570 AFIX 23 H9A 2 0.923894 0.945211 1.029453 11.00000 -1.20000 H9B 2 0.855491 0.998663 1.066798 11.00000 -1.20000 AFIX 0 C15 1 0.127479 0.652339 0.773950 11.00000 0.02743 0.05815 = 0.05078 -0.02083 -0.00171 0.00571 AFIX 23 H15A 2 0.114464 0.699789 0.752524 11.00000 -1.20000 H15B 2 0.101668 0.655805 0.815868 11.00000 -1.20000 AFIX 0 C17 1 0.109645 0.577950 0.672043 11.00000 0.03859 0.09082 = 0.05803 -0.03341 0.00593 -0.02539 AFIX 33 H17A 2 0.077038 0.535629 0.653796 11.00000 -1.50000 H17B 2 0.176184 0.569086 0.670171 11.00000 -1.50000 H17C 2 0.094647 0.623415 0.649300 11.00000 -1.50000 AFIX 0 C24 1 0.554651 0.685954 0.853235 11.00000 0.02757 0.07272 = 0.05253 -0.00378 -0.00121 0.00098 AFIX 23 H24A 2 0.569811 0.664776 0.812560 11.00000 -1.20000 H24B 2 0.601361 0.724410 0.862791 11.00000 -1.20000 AFIX 0 C23 1 0.457098 0.723994 0.849766 11.00000 0.02406 0.06371 = 0.04343 -0.01409 0.00381 0.00145 AFIX 23 H23A 2 0.434005 0.733791 0.891707 11.00000 -1.20000 H23B 2 0.462041 0.772206 0.827996 11.00000 -1.20000 AFIX 0 C12 1 0.304717 0.794074 0.734560 11.00000 0.04363 0.03664 = 0.05623 -0.00318 -0.01244 -0.00484 AFIX 23 H12A 2 0.267942 0.765464 0.704453 11.00000 -1.20000 H12B 2 0.369963 0.778880 0.730325 11.00000 -1.20000 AFIX 0 C10 1 0.337150 0.897503 0.657493 11.00000 0.12314 0.06942 = 0.08674 0.02750 -0.05245 -0.02914 AFIX 33 H10A 2 0.330961 0.951034 0.649833 11.00000 -1.50000 H10B 2 0.304345 0.869747 0.625570 11.00000 -1.50000 H10C 2 0.402469 0.883779 0.656919 11.00000 -1.50000 AFIX 0 C11 1 0.295434 0.878408 0.721131 11.00000 0.05730 0.04048 = 0.09336 0.00348 -0.03100 -0.00781 AFIX 23 H11A 2 0.327755 0.907149 0.753343 11.00000 -1.20000 H11B 2 0.229578 0.892700 0.721895 11.00000 -1.20000 AFIX 0 C20 1 0.216647 0.610045 0.981495 11.00000 0.08122 0.08350 = 0.06189 -0.01548 0.02803 -0.03052 AFIX 23 H20A 2 0.239924 0.566306 1.004376 11.00000 -1.20000 H20B 2 0.232482 0.654974 1.005597 11.00000 -1.20000 AFIX 0 C19 1 0.267469 0.614085 0.919829 11.00000 0.05802 0.10023 = 0.04398 0.00984 0.01244 0.01486 AFIX 23 H19A 2 0.245578 0.573432 0.892852 11.00000 -1.20000 H19B 2 0.334288 0.606908 0.926726 11.00000 -1.20000 AFIX 0 C25 1 0.560529 0.623940 0.901507 11.00000 0.04469 0.10617 = 0.08429 0.01722 -0.01352 0.01134 AFIX 33 H25A 2 0.622251 0.601879 0.900796 11.00000 -1.50000 H25B 2 0.514662 0.585495 0.892331 11.00000 -1.50000 H25C 2 0.548426 0.644859 0.942208 11.00000 -1.50000 AFIX 0 C21 1 0.114973 0.604545 0.977744 11.00000 0.07023 0.10430 = 0.15581 0.04209 0.04195 -0.00053 AFIX 137 H21A 2 0.089002 0.653873 0.969388 11.00000 -1.50000 H21B 2 0.090694 0.585814 1.016721 11.00000 -1.50000 H21C 2 0.097980 0.570309 0.944643 11.00000 -1.50000 PART 1 OW1 4 0.444459 0.491304 0.738987 10.50000 0.18889 0.02157 = 0.04510 0.00270 0.01954 0.01289 PART 2 OW2 4 0.421728 0.486315 0.793564 10.50000 0.14711 0.06145 = 0.06151 0.00419 0.01616 -0.00020 PART 0 REM do_zero REM R1 = 0.0538 for 5208 Fo > 4sig(Fo) and 0.0578 for all 5497 data REM 291 parameters refined using 0 restraints HKLF 4 REM Cued_Bu4N REM R1 = 0.0490 for 5208 Fo > 4sig(Fo) and 0.0528 for all 5497 data REM 290 parameters refined using 0 restraints END WGHT 0.0994 3.1497 REM Highest difference peak 1.295, deepest hole -0.388, 1-sigma level 0.101 Q1 1 0.3975 0.4915 0.6907 11.00000 0.05 1.30 Q2 1 0.9992 0.8072 1.0426 11.00000 0.05 0.87 Q3 1 0.2619 0.6488 0.7357 11.00000 0.05 0.51 ; _[local]_cod_data_source_file c3cc46242k.txt _[local]_cod_data_source_block Cued_Bu4N _cod_depositor_comments 'Adding full bibliography for 7112340--7112342.cif.' _cod_database_code 7112342 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, -z' 'x, -y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' 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 1.0000 0.81272(2) 1.0000 0.02521(14) Uani 1 2 d S . . O1 O 1.05418(15) 0.79566(13) 0.91745(10) 0.0332(5) Uani 1 1 d . . . N1 N 0.88573(16) 0.83348(13) 0.95356(11) 0.0239(5) Uani 1 1 d . . . O2 O 1.01713(15) 0.80677(15) 0.81671(10) 0.0400(5) Uani 1 1 d . . . O3 O 0.83926(18) 0.85439(18) 0.85243(11) 0.0479(7) Uani 1 1 d . . . N2 N 0.28575(18) 0.69553(16) 0.82025(12) 0.0326(6) Uani 1 1 d . . . C2 C 0.8969(2) 0.83515(17) 0.89254(14) 0.0293(6) Uani 1 1 d . . . C3 C 0.79638(19) 0.85196(18) 0.97964(13) 0.0273(6) Uani 1 1 d . . . C4 C 0.7189(2) 0.80636(18) 0.96622(13) 0.0294(6) Uani 1 1 d . . . H4A H 0.7253 0.7657 0.9387 0.035 Uiso 1 1 calc R . . C22 C 0.3889(2) 0.67231(19) 0.81534(15) 0.0338(7) Uani 1 1 d . . . H22A H 0.3956 0.6212 0.8317 0.041 Uiso 1 1 calc R . . H22B H 0.4063 0.6711 0.7715 0.041 Uiso 1 1 calc R . . C1 C 0.9980(2) 0.81056(15) 0.87260(12) 0.0283(5) Uani 1 1 d . . . C8 C 0.7858(2) 0.9143(2) 1.01973(14) 0.0340(7) Uani 1 1 d . . . C6 C 0.6221(2) 0.8804(2) 1.03522(16) 0.0420(8) Uani 1 1 d . . . H6A H 0.5647 0.8893 1.0547 0.050 Uiso 1 1 calc R . . C7 C 0.6991(2) 0.9267(2) 1.04763(17) 0.0425(8) Uani 1 1 d . . . H7A H 0.6923 0.9671 1.0754 0.051 Uiso 1 1 calc R . . C13 C 0.2710(2) 0.77656(19) 0.79961(18) 0.0408(8) Uani 1 1 d . . . H13A H 0.2044 0.7881 0.8020 0.049 Uiso 1 1 calc R . . H13B H 0.3033 0.8099 0.8287 0.049 Uiso 1 1 calc R . . C5 C 0.63208(19) 0.82102(19) 0.99345(17) 0.0366(7) Uani 1 1 d . . . H5A H 0.5806 0.7908 0.9835 0.044 Uiso 1 1 calc R . . C18 C 0.2511(2) 0.6911(2) 0.88728(16) 0.0451(8) Uani 1 1 d . . . H18A H 0.1842 0.7019 0.8877 0.054 Uiso 1 1 calc R . . H18B H 0.2822 0.7304 0.9115 0.054 Uiso 1 1 calc R . . C16 C 0.0801(2) 0.5869(2) 0.73890(18) 0.0409(7) Uani 1 1 d . . . H16A H 0.0935 0.5399 0.7609 0.049 Uiso 1 1 calc R . . H16B H 0.0126 0.5946 0.7401 0.049 Uiso 1 1 calc R . . C14 C 0.2323(2) 0.64056(19) 0.77778(15) 0.0320(7) Uani 1 1 d . . . H14A H 0.2626 0.6022 0.7557 0.038 Uiso 1 1 calc R . . C9 C 0.8639(2) 0.9714(2) 1.02775(17) 0.0423(8) Uani 1 1 d . . . H9A H 0.9239 0.9452 1.0295 0.051 Uiso 1 1 calc R . . H9B H 0.8555 0.9987 1.0668 0.051 Uiso 1 1 calc R . . C15 C 0.1275(2) 0.6523(2) 0.77395(19) 0.0455(9) Uani 1 1 d . . . H15A H 0.1145 0.6998 0.7525 0.055 Uiso 1 1 calc R . . H15B H 0.1017 0.6558 0.8159 0.055 Uiso 1 1 calc R . . C17 C 0.1096(3) 0.5780(3) 0.6720(2) 0.0625(13) Uani 1 1 d . . . H17A H 0.0770 0.5356 0.6538 0.094 Uiso 1 1 calc R . . H17B H 0.1762 0.5691 0.6702 0.094 Uiso 1 1 calc R . . H17C H 0.0946 0.6234 0.6493 0.094 Uiso 1 1 calc R . . C24 C 0.5547(3) 0.6860(3) 0.8532(2) 0.0509(9) Uani 1 1 d . . . H24A H 0.5698 0.6648 0.8126 0.061 Uiso 1 1 calc R . . H24B H 0.6014 0.7244 0.8628 0.061 Uiso 1 1 calc R . . C23 C 0.4571(2) 0.7240(3) 0.84977(18) 0.0437(8) Uani 1 1 d . . . H23A H 0.4340 0.7338 0.8917 0.052 Uiso 1 1 calc R . . H23B H 0.4620 0.7722 0.8280 0.052 Uiso 1 1 calc R . . C12 C 0.3047(3) 0.7941(2) 0.73456(19) 0.0455(8) Uani 1 1 d . . . H12A H 0.2679 0.7655 0.7045 0.055 Uiso 1 1 calc R . . H12B H 0.3700 0.7789 0.7303 0.055 Uiso 1 1 calc R . . C10 C 0.3371(5) 0.8975(3) 0.6575(3) 0.093(2) Uani 1 1 d . . . H10A H 0.3310 0.9510 0.6498 0.140 Uiso 1 1 calc R . . H10B H 0.3043 0.8697 0.6256 0.140 Uiso 1 1 calc R . . H10C H 0.4025 0.8838 0.6569 0.140 Uiso 1 1 calc R . . C11 C 0.2954(4) 0.8784(2) 0.7211(3) 0.0637(14) Uani 1 1 d . . . H11A H 0.3278 0.9071 0.7533 0.076 Uiso 1 1 calc R . . H11B H 0.2296 0.8927 0.7219 0.076 Uiso 1 1 calc R . . C20 C 0.2166(4) 0.6100(3) 0.9815(2) 0.0755(16) Uani 1 1 d . . . H20A H 0.2399 0.5663 1.0044 0.091 Uiso 1 1 calc R . . H20B H 0.2325 0.6550 1.0056 0.091 Uiso 1 1 calc R . . C19 C 0.2675(4) 0.6141(3) 0.9198(2) 0.0674(13) Uani 1 1 d . . . H19A H 0.2456 0.5734 0.8929 0.081 Uiso 1 1 calc R . . H19B H 0.3343 0.6069 0.9267 0.081 Uiso 1 1 calc R . . C25 C 0.5605(4) 0.6239(4) 0.9015(3) 0.0784(15) Uani 1 1 d . . . H25A H 0.6223 0.6019 0.9008 0.118 Uiso 1 1 calc R . . H25B H 0.5147 0.5855 0.8923 0.118 Uiso 1 1 calc R . . H25C H 0.5484 0.6449 0.9422 0.118 Uiso 1 1 calc R . . C21 C 0.1150(3) 0.6045(4) 0.9777(2) 0.110(3) Uani 1 1 d . . . H21A H 0.0890 0.6539 0.9694 0.165 Uiso 1 1 calc R . . H21B H 0.0907 0.5858 1.0167 0.165 Uiso 1 1 calc R . . H21C H 0.0980 0.5703 0.9446 0.165 Uiso 1 1 calc R . . OW1 O 0.4445(3) 0.4913(2) 0.73899(19) 0.085(3) Uani 0.50 1 d PR . 1 OW2 O 0.4217(3) 0.4863(2) 0.7936(2) 0.090(3) Uani 0.50 1 d PR A 2 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 0.0134(2) 0.0383(2) 0.0238(2) 0.000 -0.00065(19) 0.000 O1 0.0189(10) 0.0534(13) 0.0274(10) -0.0047(9) 0.0010(8) 0.0083(9) N1 0.0154(10) 0.0295(11) 0.0269(11) -0.0062(9) -0.0027(9) 0.0021(8) O2 0.0309(13) 0.0611(14) 0.0278(10) -0.0099(10) 0.0032(8) 0.0069(11) O3 0.0317(13) 0.0844(19) 0.0277(11) -0.0100(12) -0.0056(10) 0.0203(13) N2 0.0226(12) 0.0420(14) 0.0334(13) -0.0121(11) 0.0041(10) 0.0023(11) C2 0.0210(14) 0.0393(15) 0.0275(14) -0.0093(11) -0.0041(11) 0.0069(11) C3 0.0155(12) 0.0441(16) 0.0223(12) -0.0045(11) -0.0024(9) 0.0041(11) C4 0.0213(13) 0.0367(15) 0.0302(14) -0.0005(12) -0.0008(11) 0.0011(12) C22 0.0204(14) 0.0476(18) 0.0334(15) -0.0066(13) 0.0043(11) 0.0042(12) C1 0.0222(12) 0.0383(13) 0.0245(11) -0.0085(10) 0.0009(12) 0.0029(19) C8 0.0212(13) 0.0499(18) 0.0309(14) -0.0148(12) -0.0028(11) 0.0046(13) C6 0.0211(15) 0.068(2) 0.0370(18) 0.0010(15) 0.0059(13) 0.0069(14) C7 0.0266(16) 0.062(2) 0.0389(17) -0.0185(16) 0.0020(13) 0.0101(15) C13 0.0282(16) 0.0390(17) 0.055(2) -0.0169(15) -0.0046(14) 0.0011(13) C5 0.0157(11) 0.0553(17) 0.0387(16) 0.0015(17) 0.0004(12) -0.0022(11) C18 0.0284(16) 0.072(2) 0.0351(16) -0.0204(17) 0.0071(13) -0.0034(17) C16 0.0243(15) 0.0449(18) 0.053(2) -0.0056(16) 0.0018(14) -0.0039(13) C14 0.0272(16) 0.0350(15) 0.0336(15) -0.0152(13) 0.0041(12) -0.0020(13) C9 0.0217(14) 0.0568(19) 0.0485(18) -0.0302(15) -0.0042(13) 0.0057(13) C15 0.0274(17) 0.058(2) 0.051(2) -0.0208(17) -0.0017(14) 0.0057(15) C17 0.039(2) 0.091(3) 0.058(2) -0.033(2) 0.0059(18) -0.025(2) C24 0.0276(17) 0.073(3) 0.053(2) -0.004(2) -0.0012(15) 0.0010(19) C23 0.0241(16) 0.064(2) 0.0434(19) -0.0141(17) 0.0038(14) 0.0014(16) C12 0.044(2) 0.0366(17) 0.056(2) -0.0032(15) -0.0124(16) -0.0048(14) C10 0.123(6) 0.069(3) 0.087(4) 0.028(3) -0.052(4) -0.029(3) C11 0.057(3) 0.040(2) 0.093(4) 0.003(2) -0.031(3) -0.0078(18) C20 0.081(4) 0.083(3) 0.062(3) -0.015(2) 0.028(2) -0.031(3) C19 0.058(3) 0.100(4) 0.044(2) 0.010(2) 0.012(2) 0.015(3) C25 0.045(3) 0.106(4) 0.084(4) 0.017(3) -0.014(2) 0.011(2) C21 0.070(4) 0.104(5) 0.156(8) 0.042(5) 0.042(4) -0.001(4) OW1 0.189(8) 0.022(3) 0.045(3) 0.003(2) 0.020(4) 0.013(4) OW2 0.147(8) 0.061(5) 0.062(4) 0.004(3) 0.016(5) 0.000(4) 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 1 0.1397 -1 1 0 0.2189 1 0 -1 0.1815 -1 2 -2 0.2089 1 -2 -2 0.1941 0 0 -1 0.1854 -1 -1 -1 0.1683 -1 -4 -2 0.1578 -2 1 -1 0.2124 0 2 1 0.1988 2 -1 1 0.1788 -1 1 1 0.1996 0 2 -1 0.219 2 -1 -2 0.1841 3 2 3 0.1985 0 0 1 0.2037 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 N1 Cu1 N1 158.29(14) . 3_757 N1 Cu1 O1 84.10(9) . . N1 Cu1 O1 99.26(9) 3_757 . N1 Cu1 O1 99.26(9) . 3_757 N1 Cu1 O1 84.09(9) 3_757 3_757 O1 Cu1 O1 162.27(14) . 3_757 C1 O1 Cu1 113.63(18) . . C2 N1 C3 119.4(2) . . C2 N1 Cu1 114.27(19) . . C3 N1 Cu1 126.18(18) . . C13 N2 C18 106.3(3) . . C13 N2 C22 111.5(3) . . C18 N2 C22 111.3(3) . . C13 N2 C14 110.8(3) . . C18 N2 C14 111.5(2) . . C22 N2 C14 105.5(2) . . O3 C2 N1 128.0(3) . . O3 C2 C1 119.9(3) . . N1 C2 C1 112.1(2) . . C4 C3 C8 119.5(3) . . C4 C3 N1 119.6(3) . . C8 C3 N1 120.9(3) . . C5 C4 C3 120.7(3) . . C5 C4 H4A 119.7 . . C3 C4 H4A 119.7 . . C23 C22 N2 114.8(3) . . C23 C22 H22A 108.6 . . N2 C22 H22A 108.6 . . C23 C22 H22B 108.6 . . N2 C22 H22B 108.6 . . H22A C22 H22B 107.5 . . O2 C1 O1 125.5(3) . . O2 C1 C2 119.1(3) . . O1 C1 C2 115.4(2) . . C7 C8 C3 118.8(3) . . C7 C8 C9 120.1(3) . . C3 C8 C9 120.8(3) . . C5 C6 C7 119.0(3) . . C5 C6 H6A 120.5 . . C7 C6 H6A 120.5 . . C8 C7 C6 121.8(3) . . C8 C7 H7A 119.1 . . C6 C7 H7A 119.1 . . C12 C13 N2 114.9(3) . . C12 C13 H13A 108.6 . . N2 C13 H13A 108.6 . . C12 C13 H13B 108.6 . . N2 C13 H13B 108.6 . . H13A C13 H13B 107.5 . . C6 C5 C4 120.2(3) . . C6 C5 H5A 119.9 . . C4 C5 H5A 119.9 . . N2 C18 C19 115.0(3) . . N2 C18 H18A 108.5 . . C19 C18 H18A 108.5 . . N2 C18 H18B 108.5 . . C19 C18 H18B 108.5 . . H18A C18 H18B 107.5 . . C17 C16 C15 115.0(3) . . C17 C16 H16A 108.5 . . C15 C16 H16A 108.5 . . C17 C16 H16B 108.5 . . C15 C16 H16B 108.5 . . H16A C16 H16B 107.5 . . C15 C14 N2 115.9(3) . . C15 C14 H14A 122.0 . . N2 C14 H14A 122.0 . . C8 C9 C9 110.1(3) . 4_577 C8 C9 H9A 109.6 . . C9 C9 H9A 109.6 4_577 . C8 C9 H9B 109.6 . . C9 C9 H9B 109.6 4_577 . H9A C9 H9B 108.1 . . C14 C15 C16 111.0(3) . . C14 C15 H15A 109.4 . . C16 C15 H15A 109.4 . . C14 C15 H15B 109.4 . . C16 C15 H15B 109.4 . . H15A C15 H15B 108.0 . . C16 C17 H17A 109.5 . . C16 C17 H17B 109.5 . . H17A C17 H17B 109.5 . . C16 C17 H17C 109.5 . . H17A C17 H17C 109.5 . . H17B C17 H17C 109.5 . . C25 C24 C23 113.4(4) . . C25 C24 H24A 108.9 . . C23 C24 H24A 108.9 . . C25 C24 H24B 108.9 . . C23 C24 H24B 108.9 . . H24A C24 H24B 107.7 . . C22 C23 C24 109.8(3) . . C22 C23 H23A 109.7 . . C24 C23 H23A 109.7 . . C22 C23 H23B 109.7 . . C24 C23 H23B 109.7 . . H23A C23 H23B 108.2 . . C13 C12 C11 110.4(4) . . C13 C12 H12A 109.6 . . C11 C12 H12A 109.6 . . C13 C12 H12B 109.6 . . C11 C12 H12B 109.6 . . H12A C12 H12B 108.1 . . C11 C10 H10A 109.5 . . C11 C10 H10B 109.5 . . H10A C10 H10B 109.5 . . C11 C10 H10C 109.5 . . H10A C10 H10C 109.5 . . H10B C10 H10C 109.5 . . C12 C11 C10 110.6(5) . . C12 C11 H11A 109.5 . . C10 C11 H11A 109.5 . . C12 C11 H11B 109.5 . . C10 C11 H11B 109.5 . . H11A C11 H11B 108.1 . . C21 C20 C19 115.7(5) . . C21 C20 H20A 108.4 . . C19 C20 H20A 108.4 . . C21 C20 H20B 108.4 . . C19 C20 H20B 108.4 . . H20A C20 H20B 107.4 . . C20 C19 C18 111.4(4) . . C20 C19 H19A 109.4 . . C18 C19 H19A 109.4 . . C20 C19 H19B 109.4 . . C18 C19 H19B 109.4 . . H19A C19 H19B 108.0 . . C24 C25 H25A 109.5 . . C24 C25 H25B 109.5 . . H25A C25 H25B 109.5 . . C24 C25 H25C 109.5 . . H25A C25 H25C 109.5 . . H25B C25 H25C 109.5 . . C20 C21 H21A 109.5 . . C20 C21 H21B 109.5 . . H21A C21 H21B 109.5 . . C20 C21 H21C 109.5 . . H21A C21 H21C 109.5 . . H21B C21 H21C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cu1 N1 1.939(2) . Cu1 N1 1.939(2) 3_757 Cu1 O1 1.948(2) . Cu1 O1 1.948(2) 3_757 O1 C1 1.276(4) . N1 C2 1.314(4) . N1 C3 1.425(4) . O2 C1 1.227(3) . O3 C2 1.233(4) . N2 C13 1.507(5) . N2 C18 1.517(4) . N2 C22 1.526(4) . N2 C14 1.529(4) . C2 C1 1.561(4) . C3 C4 1.393(4) . C3 C8 1.400(4) . C4 C5 1.389(4) . C4 H4A 0.9300 . C22 C23 1.520(5) . C22 H22A 0.9700 . C22 H22B 0.9700 . C8 C7 1.387(5) . C8 C9 1.508(5) . C6 C5 1.382(5) . C6 C7 1.391(5) . C6 H6A 0.9300 . C7 H7A 0.9300 . C13 C12 1.502(6) . C13 H13A 0.9700 . C13 H13B 0.9700 . C5 H5A 0.9300 . C18 C19 1.540(7) . C18 H18A 0.9700 . C18 H18B 0.9700 . C16 C17 1.497(6) . C16 C15 1.530(5) . C16 H16A 0.9700 . C16 H16B 0.9700 . C14 C15 1.507(5) . C14 H14A 0.9300 . C9 C9 1.555(9) 4_577 C9 H9A 0.9700 . C9 H9B 0.9700 . C15 H15A 0.9700 . C15 H15B 0.9700 . C17 H17A 0.9600 . C17 H17B 0.9600 . C17 H17C 0.9600 . C24 C25 1.504(8) . C24 C23 1.542(5) . C24 H24A 0.9700 . C24 H24B 0.9700 . C23 H23A 0.9700 . C23 H23B 0.9700 . C12 C11 1.517(5) . C12 H12A 0.9700 . C12 H12B 0.9700 . C10 C11 1.521(9) . C10 H10A 0.9600 . C10 H10B 0.9600 . C10 H10C 0.9600 . C11 H11A 0.9700 . C11 H11B 0.9700 . C20 C21 1.452(7) . C20 C19 1.505(6) . C20 H20A 0.9700 . C20 H20B 0.9700 . C19 H19A 0.9700 . C19 H19B 0.9700 . C25 H25A 0.9600 . C25 H25B 0.9600 . C25 H25C 0.9600 . C21 H21A 0.9600 . C21 H21B 0.9600 . C21 H21C 0.9600 . OW1 OW1 1.609(9) 2_665