#------------------------------------------------------------------------------ #$Date: 2020-08-18 04:59:11 +0300 (Tue, 18 Aug 2020) $ #$Revision: 255414 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705173.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_7705173 loop_ _publ_author_name 'Li, Yinghua' 'Fan, Weibin' 'Zhang, Zilong' 'Xie, Xingkun' 'Xiang, Shiqun' 'Huang, Deguang' _publ_section_title ; Copper(II)-Hydroxide Facilitated C−C Bond Formation: Carboxamido Pyridine System versus Methylimino Pyridine System ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT02288H _journal_year 2020 _chemical_formula_moiety 'C26 H28 Cu N4 O3' _chemical_formula_sum 'C26 H28 Cu N4 O3' _chemical_formula_weight 508.06 _chemical_name_common '[Cu(NNN-pincer)-DMF]' _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-07-21 deposited with the CCDC. 2020-08-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.3269(3) _cell_length_b 13.8051(2) _cell_length_c 11.6358(2) _cell_measurement_reflns_used 4978 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 76.3100 _cell_measurement_theta_min 4.2930 _cell_volume 2462.01(7) _computing_cell_refinement 'CrysAlisPro, Agilent Technologies' _computing_data_collection 'CrysAlisPro, Agilent Technologies' _computing_data_reduction 'CrysAlisPro, Agilent Technologies' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.5594 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_unetI/netI 0.0305 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7894 _diffrn_reflns_point_group_measured_fraction_full 0.859 _diffrn_reflns_point_group_measured_fraction_max 0.834 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.988 _diffrn_reflns_theta_min 4.310 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.532 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.95018 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.' ; _exptl_crystal_colour green-brown _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1060 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.160 _refine_diff_density_max 0.446 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.070 _refine_ls_abs_structure_details ; Flack x determined using 1472 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.019(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 4289 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0366 _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^)+(0.0615P)^2^+1.6778P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0998 _refine_ls_wR_factor_ref 0.1025 _reflns_Friedel_coverage 0.599 _reflns_Friedel_fraction_full 0.703 _reflns_Friedel_fraction_max 0.659 _reflns_number_gt 4115 _reflns_number_total 4289 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02288h2.cif _cod_data_source_block Complex1 _cod_original_cell_volume 2461.99(7) _cod_database_code 7705173 _shelx_shelxl_version_number 2018/3 _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 0.749 _shelx_estimated_absorpt_t_max 0.792 _shelx_res_file ; TITL hdg201 in Pna21 #33 full.res created by SHELXL-2018/3 at 15:37:55 on 21-Jul-2020 CELL 1.54184 15.32686 13.80507 11.63576 90 90 90 ZERR 4 0.00025 0.0002 0.0002 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,0.5+Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SFAC C H Cu N O UNIT 104 112 4 16 12 TEMP -173 SIZE 0.20 0.18 0.16 REM green-brown block OMIT 0 152 ACTA L.S. 8 PLAN 8 BOND $H CONF fmap 2 WGHT 0.061500 1.677800 FVAR 5.26659 CU1 3 0.618484 0.722570 0.279599 11.00000 0.01512 0.00936 = 0.01046 -0.00047 -0.00157 0.00201 O1 5 0.468542 0.810759 0.012266 11.00000 0.03358 0.01686 = 0.01559 0.00333 -0.01030 0.00189 O2 5 0.667986 0.908557 0.542366 11.00000 0.02156 0.01663 = 0.01503 -0.00466 -0.00282 0.00211 O3 5 0.666613 0.593337 0.290963 11.00000 0.01891 0.01243 = 0.01703 -0.00023 -0.00132 0.00233 N1 4 0.557155 0.717266 0.130545 11.00000 0.01825 0.01215 = 0.01442 0.00140 -0.00097 -0.00004 N2 4 0.571694 0.851413 0.277266 11.00000 0.01517 0.01184 = 0.01358 -0.00007 0.00030 0.00056 N3 4 0.666444 0.769992 0.427519 11.00000 0.01481 0.01127 = 0.01257 -0.00014 -0.00006 0.00153 N4 4 0.676383 0.430966 0.276292 11.00000 0.01496 0.01030 = 0.01965 -0.00187 -0.00126 0.00181 C1 1 0.511557 0.797028 0.100259 11.00000 0.02035 0.01323 = 0.01448 0.00064 -0.00040 -0.00027 C2 1 0.519198 0.875679 0.190849 11.00000 0.01590 0.01207 = 0.01287 0.00057 -0.00141 -0.00133 C3 1 0.476357 0.964858 0.192076 11.00000 0.01778 0.01295 = 0.01685 0.00124 -0.00037 0.00265 AFIX 43 H3A 2 0.436986 0.982742 0.132694 11.00000 -1.20000 AFIX 0 C4 1 0.493694 1.026504 0.283884 11.00000 0.01950 0.01185 = 0.01854 0.00103 0.00404 0.00439 AFIX 43 H4A 2 0.466631 1.088389 0.285946 11.00000 -1.20000 AFIX 0 C5 1 0.549683 0.999984 0.372950 11.00000 0.01840 0.01051 = 0.01622 -0.00145 0.00148 0.00029 AFIX 43 H5A 2 0.561738 1.042680 0.434980 11.00000 -1.20000 AFIX 0 C6 1 0.587175 0.908213 0.367067 11.00000 0.01400 0.01415 = 0.01395 -0.00085 0.00058 0.00025 C7 1 0.645712 0.862166 0.455993 11.00000 0.01305 0.01257 = 0.01371 -0.00112 0.00163 0.00115 C8 1 0.715065 0.713426 0.507089 11.00000 0.01334 0.01382 = 0.01367 -0.00194 -0.00362 -0.00089 C9 1 0.677492 0.684345 0.612084 11.00000 0.01861 0.01765 = 0.01471 -0.00143 -0.00046 -0.00245 C10 1 0.723650 0.620688 0.681352 11.00000 0.02941 0.02121 = 0.01622 0.00252 -0.00528 -0.00708 AFIX 43 H10A 2 0.698808 0.599865 0.751955 11.00000 -1.20000 AFIX 0 C11 1 0.805330 0.586816 0.649642 11.00000 0.03080 0.01917 = 0.02622 0.00567 -0.01238 0.00297 AFIX 43 H11A 2 0.835239 0.541746 0.697124 11.00000 -1.20000 AFIX 0 C12 1 0.843294 0.619039 0.548135 11.00000 0.01893 0.01887 = 0.02872 -0.00549 -0.00662 0.00398 AFIX 43 H12A 2 0.900259 0.597860 0.528030 11.00000 -1.20000 AFIX 0 C13 1 0.798990 0.681509 0.476306 11.00000 0.01517 0.01418 = 0.01695 -0.00458 -0.00163 -0.00011 C14 1 0.839976 0.715281 0.366040 11.00000 0.01914 0.02169 = 0.02472 -0.00402 0.00728 0.00073 AFIX 33 H14A 2 0.799738 0.758945 0.326033 11.00000 -1.50000 H14B 2 0.894380 0.749701 0.383084 11.00000 -1.50000 H14C 2 0.852539 0.659220 0.317093 11.00000 -1.50000 AFIX 0 C15 1 0.587941 0.718581 0.648205 11.00000 0.02132 0.02761 = 0.02103 -0.00343 0.00748 -0.00404 AFIX 33 H15A 2 0.564674 0.762880 0.589965 11.00000 -1.50000 H15B 2 0.548953 0.662701 0.655999 11.00000 -1.50000 H15C 2 0.592124 0.752363 0.722075 11.00000 -1.50000 AFIX 0 C16 1 0.552046 0.633563 0.060117 11.00000 0.02239 0.01290 = 0.00810 0.00127 -0.00348 0.00012 C17 1 0.628271 0.596724 0.010293 11.00000 0.02279 0.01570 = 0.01188 0.00212 -0.00109 0.00117 C18 1 0.624756 0.507063 -0.045543 11.00000 0.02628 0.01973 = 0.01527 -0.00128 0.00413 0.00446 AFIX 43 H18A 2 0.676358 0.481058 -0.078614 11.00000 -1.20000 AFIX 0 C19 1 0.547628 0.455576 -0.053517 11.00000 0.03403 0.01624 = 0.01760 -0.00390 -0.00139 -0.00026 AFIX 43 H19A 2 0.546447 0.394725 -0.091612 11.00000 -1.20000 AFIX 0 C20 1 0.471726 0.493290 -0.005487 11.00000 0.02328 0.01706 = 0.01498 0.00125 -0.00504 -0.00358 AFIX 43 H20A 2 0.418759 0.457926 -0.011618 11.00000 -1.20000 AFIX 0 C21 1 0.472167 0.582287 0.051582 11.00000 0.02127 0.01466 = 0.01101 0.00133 -0.00307 0.00022 C22 1 0.389893 0.619357 0.107346 11.00000 0.02022 0.02011 = 0.02654 -0.00187 -0.00035 0.00090 AFIX 33 H22A 2 0.401451 0.682251 0.143313 11.00000 -1.50000 H22B 2 0.344287 0.626698 0.048961 11.00000 -1.50000 H22C 2 0.370463 0.573216 0.166012 11.00000 -1.50000 AFIX 0 C23 1 0.713696 0.650934 0.017447 11.00000 0.02084 0.02532 = 0.02310 -0.00052 0.00352 -0.00268 AFIX 33 H23A 2 0.704887 0.711905 0.058993 11.00000 -1.50000 H23B 2 0.756727 0.611280 0.058280 11.00000 -1.50000 H23C 2 0.734901 0.664791 -0.060290 11.00000 -1.50000 AFIX 0 C24 1 0.634828 0.513001 0.262347 11.00000 0.01570 0.01271 = 0.01205 -0.00010 -0.00045 0.00158 AFIX 43 H24A 2 0.578208 0.511713 0.229162 11.00000 -1.20000 AFIX 0 C25 1 0.764690 0.426779 0.322637 11.00000 0.01796 0.01635 = 0.03596 -0.00327 -0.00795 0.00376 AFIX 33 H25A 2 0.783971 0.359162 0.326204 11.00000 -1.50000 H25B 2 0.804139 0.463620 0.272810 11.00000 -1.50000 H25C 2 0.765311 0.454742 0.400047 11.00000 -1.50000 AFIX 0 C26 1 0.637623 0.338640 0.240384 11.00000 0.02685 0.01311 = 0.03858 -0.00576 -0.00607 -0.00344 AFIX 33 H26A 2 0.678132 0.285676 0.257640 11.00000 -1.50000 H26B 2 0.582799 0.328291 0.281949 11.00000 -1.50000 H26C 2 0.626047 0.340275 0.157576 11.00000 -1.50000 AFIX 0 HKLF 4 REM hdg201 in Pna21 #33 REM wR2 = 0.1025, GooF = S = 1.057, Restrained GooF = 1.057 for all data REM R1 = 0.0366 for 4115 Fo > 4sig(Fo) and 0.0388 for all 4289 data REM 307 parameters refined using 1 restraints END WGHT 0.0615 1.6778 REM Highest difference peak 0.446, deepest hole -0.538, 1-sigma level 0.070 Q1 1 0.9005 0.6966 0.3680 11.00000 0.05 0.45 Q2 1 0.3389 0.5668 0.0969 11.00000 0.05 0.44 Q3 1 0.8085 0.6857 0.2918 11.00000 0.05 0.44 Q4 1 0.5437 0.7017 0.5922 11.00000 0.05 0.44 Q5 1 0.7096 0.7125 -0.0147 11.00000 0.05 0.41 Q6 1 0.6745 0.3060 0.1866 11.00000 0.05 0.40 Q7 1 0.3924 0.6377 0.1914 11.00000 0.05 0.39 Q8 1 0.8347 0.8010 0.3489 11.00000 0.05 0.37 ; _shelx_res_checksum 49674 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.61848(3) 0.72257(3) 0.27960(6) 0.01165(14) Uani 1 1 d . . . . . O1 O 0.4685(2) 0.8108(2) 0.0123(3) 0.0220(6) Uani 1 1 d . . . . . O2 O 0.66799(18) 0.90856(19) 0.5424(2) 0.0177(6) Uani 1 1 d . . . . . O3 O 0.66661(16) 0.59334(17) 0.2910(3) 0.0161(5) Uani 1 1 d . . . . . N1 N 0.5572(2) 0.7173(2) 0.1305(3) 0.0149(6) Uani 1 1 d . . . . . N2 N 0.57169(18) 0.85141(19) 0.2773(3) 0.0135(5) Uani 1 1 d . . . . . N3 N 0.6664(2) 0.7700(2) 0.4275(3) 0.0129(6) Uani 1 1 d . . . . . N4 N 0.67638(18) 0.43097(19) 0.2763(3) 0.0150(6) Uani 1 1 d . . . . . C1 C 0.5116(3) 0.7970(3) 0.1003(3) 0.0160(7) Uani 1 1 d . . . . . C2 C 0.5192(2) 0.8757(3) 0.1908(3) 0.0136(7) Uani 1 1 d . . . . . C3 C 0.4764(2) 0.9649(3) 0.1921(4) 0.0159(7) Uani 1 1 d . . . . . H3A H 0.436986 0.982742 0.132694 0.019 Uiso 1 1 calc R U . . . C4 C 0.4937(2) 1.0265(2) 0.2839(4) 0.0166(6) Uani 1 1 d . . . . . H4A H 0.466631 1.088389 0.285946 0.020 Uiso 1 1 calc R U . . . C5 C 0.5497(3) 1.0000(3) 0.3729(3) 0.0150(7) Uani 1 1 d . . . . . H5A H 0.561738 1.042680 0.434980 0.018 Uiso 1 1 calc R U . . . C6 C 0.5872(2) 0.9082(3) 0.3671(3) 0.0140(7) Uani 1 1 d . . . . . C7 C 0.6457(2) 0.8622(3) 0.4560(3) 0.0131(7) Uani 1 1 d . . . . . C8 C 0.7151(2) 0.7134(3) 0.5071(3) 0.0136(7) Uani 1 1 d . . . . . C9 C 0.6775(3) 0.6843(3) 0.6121(3) 0.0170(8) Uani 1 1 d . . . . . C10 C 0.7236(3) 0.6207(3) 0.6814(4) 0.0223(8) Uani 1 1 d . . . . . H10A H 0.698808 0.599865 0.751955 0.027 Uiso 1 1 calc R U . . . C11 C 0.8053(3) 0.5868(3) 0.6496(4) 0.0254(9) Uani 1 1 d . . . . . H11A H 0.835239 0.541746 0.697124 0.030 Uiso 1 1 calc R U . . . C12 C 0.8433(3) 0.6190(3) 0.5481(4) 0.0222(8) Uani 1 1 d . . . . . H12A H 0.900259 0.597860 0.528030 0.027 Uiso 1 1 calc R U . . . C13 C 0.7990(2) 0.6815(3) 0.4763(3) 0.0154(7) Uani 1 1 d . . . . . C14 C 0.8400(3) 0.7153(3) 0.3660(4) 0.0218(9) Uani 1 1 d . . . . . H14A H 0.799738 0.758945 0.326033 0.033 Uiso 1 1 calc R U . . . H14B H 0.894380 0.749701 0.383084 0.033 Uiso 1 1 calc R U . . . H14C H 0.852539 0.659220 0.317093 0.033 Uiso 1 1 calc R U . . . C15 C 0.5879(3) 0.7186(3) 0.6482(4) 0.0233(9) Uani 1 1 d . . . . . H15A H 0.564674 0.762880 0.589965 0.035 Uiso 1 1 calc R U . . . H15B H 0.548953 0.662701 0.655999 0.035 Uiso 1 1 calc R U . . . H15C H 0.592124 0.752363 0.722075 0.035 Uiso 1 1 calc R U . . . C16 C 0.5520(3) 0.6336(3) 0.0601(3) 0.0145(7) Uani 1 1 d . . . . . C17 C 0.6283(3) 0.5967(3) 0.0103(3) 0.0168(8) Uani 1 1 d . . . . . C18 C 0.6248(3) 0.5071(3) -0.0455(4) 0.0204(8) Uani 1 1 d . . . . . H18A H 0.676358 0.481058 -0.078614 0.025 Uiso 1 1 calc R U . . . C19 C 0.5476(3) 0.4556(3) -0.0535(4) 0.0226(8) Uani 1 1 d . . . . . H19A H 0.546447 0.394725 -0.091612 0.027 Uiso 1 1 calc R U . . . C20 C 0.4717(3) 0.4933(3) -0.0055(4) 0.0184(8) Uani 1 1 d . . . . . H20A H 0.418759 0.457926 -0.011618 0.022 Uiso 1 1 calc R U . . . C21 C 0.4722(3) 0.5823(3) 0.0516(3) 0.0156(7) Uani 1 1 d . . . . . C22 C 0.3899(3) 0.6194(3) 0.1073(4) 0.0223(8) Uani 1 1 d . . . . . H22A H 0.401451 0.682251 0.143313 0.033 Uiso 1 1 calc R U . . . H22B H 0.344287 0.626698 0.048961 0.033 Uiso 1 1 calc R U . . . H22C H 0.370463 0.573216 0.166012 0.033 Uiso 1 1 calc R U . . . C23 C 0.7137(3) 0.6509(3) 0.0174(4) 0.0231(9) Uani 1 1 d . . . . . H23A H 0.704887 0.711905 0.058993 0.035 Uiso 1 1 calc R U . . . H23B H 0.756727 0.611280 0.058280 0.035 Uiso 1 1 calc R U . . . H23C H 0.734901 0.664791 -0.060290 0.035 Uiso 1 1 calc R U . . . C24 C 0.6348(2) 0.5130(2) 0.2623(3) 0.0135(7) Uani 1 1 d . . . . . H24A H 0.578208 0.511713 0.229162 0.016 Uiso 1 1 calc R U . . . C25 C 0.7647(3) 0.4268(3) 0.3226(4) 0.0234(9) Uani 1 1 d . . . . . H25A H 0.783971 0.359162 0.326204 0.035 Uiso 1 1 calc R U . . . H25B H 0.804139 0.463620 0.272810 0.035 Uiso 1 1 calc R U . . . H25C H 0.765311 0.454742 0.400047 0.035 Uiso 1 1 calc R U . . . C26 C 0.6376(3) 0.3386(3) 0.2404(4) 0.0262(9) Uani 1 1 d . . . . . H26A H 0.678132 0.285676 0.257640 0.039 Uiso 1 1 calc R U . . . H26B H 0.582799 0.328291 0.281949 0.039 Uiso 1 1 calc R U . . . H26C H 0.626047 0.340275 0.157576 0.039 Uiso 1 1 calc R U . . . 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 0.0151(2) 0.0094(2) 0.0105(2) -0.0005(2) -0.0016(3) 0.00201(16) O1 0.0336(16) 0.0169(13) 0.0156(14) 0.0033(11) -0.0103(12) 0.0019(12) O2 0.0216(13) 0.0166(12) 0.0150(13) -0.0047(11) -0.0028(11) 0.0021(11) O3 0.0189(11) 0.0124(10) 0.0170(13) -0.0002(11) -0.0013(12) 0.0023(9) N1 0.0183(16) 0.0121(14) 0.0144(16) 0.0014(12) -0.0010(13) 0.0000(12) N2 0.0152(12) 0.0118(11) 0.0136(13) -0.0001(15) 0.0003(16) 0.0006(10) N3 0.0148(14) 0.0113(14) 0.0126(15) -0.0001(11) -0.0001(13) 0.0015(11) N4 0.0150(12) 0.0103(12) 0.0196(15) -0.0019(15) -0.0013(16) 0.0018(10) C1 0.0203(18) 0.0132(16) 0.0145(18) 0.0006(15) -0.0004(15) -0.0003(14) C2 0.0159(16) 0.0121(16) 0.0129(16) 0.0006(14) -0.0014(15) -0.0013(13) C3 0.0178(17) 0.0129(16) 0.0168(18) 0.0012(15) -0.0004(15) 0.0026(14) C4 0.0195(15) 0.0118(13) 0.0185(17) 0.0010(18) 0.0040(19) 0.0044(12) C5 0.0184(17) 0.0105(15) 0.0162(18) -0.0015(14) 0.0015(15) 0.0003(14) C6 0.0140(17) 0.0142(16) 0.0139(17) -0.0008(14) 0.0006(14) 0.0003(13) C7 0.0131(16) 0.0126(15) 0.0137(17) -0.0011(14) 0.0016(14) 0.0012(13) C8 0.0133(17) 0.0138(16) 0.0137(17) -0.0019(14) -0.0036(14) -0.0009(13) C9 0.0186(18) 0.0177(17) 0.0147(18) -0.0014(15) -0.0005(15) -0.0024(14) C10 0.029(2) 0.0212(19) 0.0162(19) 0.0025(16) -0.0053(17) -0.0071(16) C11 0.031(2) 0.0192(19) 0.026(2) 0.0057(16) -0.0124(19) 0.0030(16) C12 0.0189(18) 0.0189(19) 0.029(2) -0.0055(17) -0.0066(18) 0.0040(15) C13 0.0152(17) 0.0142(16) 0.0170(18) -0.0046(14) -0.0016(15) -0.0001(14) C14 0.019(2) 0.0217(19) 0.025(2) -0.0040(16) 0.0073(17) 0.0007(15) C15 0.021(2) 0.028(2) 0.021(2) -0.0034(16) 0.0075(17) -0.0040(16) C16 0.0224(18) 0.0129(16) 0.0081(16) 0.0013(13) -0.0035(14) 0.0001(14) C17 0.0228(19) 0.0157(17) 0.0119(18) 0.0021(14) -0.0011(15) 0.0012(15) C18 0.026(2) 0.0197(18) 0.0153(19) -0.0013(16) 0.0041(16) 0.0045(16) C19 0.034(2) 0.0162(17) 0.0176(19) -0.0039(15) -0.0014(17) -0.0003(17) C20 0.0233(19) 0.0171(17) 0.0150(18) 0.0012(15) -0.0050(15) -0.0036(15) C21 0.0213(19) 0.0147(17) 0.0110(17) 0.0013(14) -0.0031(15) 0.0002(14) C22 0.0202(19) 0.0201(19) 0.027(2) -0.0019(17) -0.0003(17) 0.0009(15) C23 0.0208(19) 0.025(2) 0.023(2) -0.0005(17) 0.0035(17) -0.0027(17) C24 0.0157(15) 0.0127(14) 0.012(2) -0.0001(14) -0.0004(14) 0.0016(12) C25 0.0180(18) 0.0164(18) 0.036(2) -0.0033(16) -0.0079(17) 0.0038(15) C26 0.027(2) 0.0131(17) 0.039(3) -0.0058(17) -0.0061(18) -0.0034(16) 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' Cu Cu -1.9646 0.5888 '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' 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 _geom_angle_publ_flag N2 Cu1 O3 176.85(16) . . ? N2 Cu1 N1 81.02(14) . . ? O3 Cu1 N1 101.97(13) . . ? N2 Cu1 N3 81.07(14) . . ? O3 Cu1 N3 95.96(13) . . ? N1 Cu1 N3 162.07(12) . . ? C24 O3 Cu1 130.4(2) . . ? C1 N1 C16 119.0(3) . . ? C1 N1 Cu1 116.4(3) . . ? C16 N1 Cu1 124.3(2) . . ? C6 N2 C2 123.6(3) . . ? C6 N2 Cu1 118.0(3) . . ? C2 N2 Cu1 118.1(3) . . ? C7 N3 C8 118.7(3) . . ? C7 N3 Cu1 115.9(3) . . ? C8 N3 Cu1 125.3(2) . . ? C24 N4 C25 122.1(3) . . ? C24 N4 C26 121.3(3) . . ? C25 N4 C26 116.5(3) . . ? O1 C1 N1 128.2(4) . . ? O1 C1 C2 120.5(3) . . ? N1 C1 C2 111.2(3) . . ? N2 C2 C3 119.9(3) . . ? N2 C2 C1 113.0(3) . . ? C3 C2 C1 127.0(3) . . ? C4 C3 C2 117.2(3) . . ? C4 C3 H3A 121.4 . . ? C2 C3 H3A 121.4 . . ? C3 C4 C5 121.8(3) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C6 C5 C4 117.1(3) . . ? C6 C5 H5A 121.4 . . ? C4 C5 H5A 121.4 . . ? N2 C6 C5 120.1(3) . . ? N2 C6 C7 113.4(3) . . ? C5 C6 C7 126.5(3) . . ? O2 C7 N3 128.3(4) . . ? O2 C7 C6 120.1(3) . . ? N3 C7 C6 111.6(3) . . ? C13 C8 C9 120.4(4) . . ? C13 C8 N3 119.1(4) . . ? C9 C8 N3 120.4(3) . . ? C10 C9 C8 118.4(4) . . ? C10 C9 C15 120.0(4) . . ? C8 C9 C15 121.5(4) . . ? C11 C10 C9 121.3(4) . . ? C11 C10 H10A 119.3 . . ? C9 C10 H10A 119.3 . . ? C10 C11 C12 119.8(4) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C13 C12 C11 120.6(4) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C12 C13 C8 119.5(4) . . ? C12 C13 C14 120.4(4) . . ? C8 C13 C14 120.2(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C9 C15 H15A 109.5 . . ? C9 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C9 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 120.7(3) . . ? C17 C16 N1 119.3(3) . . ? C21 C16 N1 119.7(3) . . ? C18 C17 C16 118.8(4) . . ? C18 C17 C23 119.8(4) . . ? C16 C17 C23 121.4(4) . . ? C19 C18 C17 121.3(4) . . ? C19 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C18 C19 C20 119.7(4) . . ? C18 C19 H19A 120.1 . . ? C20 C19 H19A 120.1 . . ? C19 C20 C21 121.1(4) . . ? C19 C20 H20A 119.5 . . ? C21 C20 H20A 119.5 . . ? C20 C21 C16 118.5(4) . . ? C20 C21 C22 119.9(4) . . ? C16 C21 C22 121.5(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C23 H23A 109.5 . . ? C17 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C17 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O3 C24 N4 122.8(3) . . ? O3 C24 H24A 118.6 . . ? N4 C24 H24A 118.6 . . ? N4 C25 H25A 109.5 . . ? N4 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N4 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N4 C26 H26A 109.5 . . ? N4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.918(3) . ? Cu1 O3 1.935(2) . ? Cu1 N1 1.974(3) . ? Cu1 N3 1.983(3) . ? O1 C1 1.232(5) . ? O2 C7 1.240(5) . ? O3 C24 1.256(4) . ? N1 C1 1.351(5) . ? N1 C16 1.419(5) . ? N2 C6 1.328(5) . ? N2 C2 1.331(5) . ? N3 C7 1.353(5) . ? N3 C8 1.422(5) . ? N4 C24 1.309(4) . ? N4 C25 1.458(5) . ? N4 C26 1.467(4) . ? C1 C2 1.518(5) . ? C2 C3 1.395(5) . ? C3 C4 1.391(6) . ? C3 H3A 0.9500 . ? C4 C5 1.394(6) . ? C4 H4A 0.9500 . ? C5 C6 1.393(5) . ? C5 H5A 0.9500 . ? C6 C7 1.510(5) . ? C8 C13 1.406(5) . ? C8 C9 1.409(6) . ? C9 C10 1.386(6) . ? C9 C15 1.511(6) . ? C10 C11 1.386(6) . ? C10 H10A 0.9500 . ? C11 C12 1.390(7) . ? C11 H11A 0.9500 . ? C12 C13 1.380(6) . ? C12 H12A 0.9500 . ? C13 C14 1.503(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.400(6) . ? C16 C21 1.418(5) . ? C17 C18 1.399(6) . ? C17 C23 1.510(5) . ? C18 C19 1.382(6) . ? C18 H18A 0.9500 . ? C19 C20 1.392(6) . ? C19 H19A 0.9500 . ? C20 C21 1.397(5) . ? C20 H20A 0.9500 . ? C21 C22 1.508(6) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N1 C1 O1 -5.5(6) . . . . ? Cu1 N1 C1 O1 179.9(3) . . . . ? C16 N1 C1 C2 175.2(3) . . . . ? Cu1 N1 C1 C2 0.6(4) . . . . ? C6 N2 C2 C3 -0.5(5) . . . . ? Cu1 N2 C2 C3 173.2(3) . . . . ? C6 N2 C2 C1 -178.9(3) . . . . ? Cu1 N2 C2 C1 -5.2(4) . . . . ? O1 C1 C2 N2 -176.5(3) . . . . ? N1 C1 C2 N2 2.8(5) . . . . ? O1 C1 C2 C3 5.2(6) . . . . ? N1 C1 C2 C3 -175.4(4) . . . . ? N2 C2 C3 C4 2.3(5) . . . . ? C1 C2 C3 C4 -179.6(4) . . . . ? C2 C3 C4 C5 -1.6(6) . . . . ? C3 C4 C5 C6 -0.7(6) . . . . ? C2 N2 C6 C5 -1.9(6) . . . . ? Cu1 N2 C6 C5 -175.6(3) . . . . ? C2 N2 C6 C7 177.3(3) . . . . ? Cu1 N2 C6 C7 3.6(4) . . . . ? C4 C5 C6 N2 2.5(5) . . . . ? C4 C5 C6 C7 -176.6(4) . . . . ? C8 N3 C7 O2 4.7(6) . . . . ? Cu1 N3 C7 O2 -179.2(3) . . . . ? C8 N3 C7 C6 -174.7(3) . . . . ? Cu1 N3 C7 C6 1.4(4) . . . . ? N2 C6 C7 O2 177.4(3) . . . . ? C5 C6 C7 O2 -3.4(6) . . . . ? N2 C6 C7 N3 -3.2(5) . . . . ? C5 C6 C7 N3 176.0(4) . . . . ? C7 N3 C8 C13 -116.2(4) . . . . ? Cu1 N3 C8 C13 68.1(4) . . . . ? C7 N3 C8 C9 68.0(5) . . . . ? Cu1 N3 C8 C9 -107.7(4) . . . . ? C13 C8 C9 C10 -2.7(5) . . . . ? N3 C8 C9 C10 173.1(3) . . . . ? C13 C8 C9 C15 179.1(4) . . . . ? N3 C8 C9 C15 -5.1(5) . . . . ? C8 C9 C10 C11 0.7(6) . . . . ? C15 C9 C10 C11 179.0(4) . . . . ? C9 C10 C11 C12 1.9(6) . . . . ? C10 C11 C12 C13 -2.6(6) . . . . ? C11 C12 C13 C8 0.7(6) . . . . ? C11 C12 C13 C14 -179.3(4) . . . . ? C9 C8 C13 C12 2.0(5) . . . . ? N3 C8 C13 C12 -173.8(3) . . . . ? C9 C8 C13 C14 -178.0(3) . . . . ? N3 C8 C13 C14 6.2(5) . . . . ? C1 N1 C16 C17 120.1(4) . . . . ? Cu1 N1 C16 C17 -65.7(4) . . . . ? C1 N1 C16 C21 -66.9(5) . . . . ? Cu1 N1 C16 C21 107.2(4) . . . . ? C21 C16 C17 C18 -1.7(6) . . . . ? N1 C16 C17 C18 171.2(4) . . . . ? C21 C16 C17 C23 179.3(4) . . . . ? N1 C16 C17 C23 -7.8(6) . . . . ? C16 C17 C18 C19 0.9(6) . . . . ? C23 C17 C18 C19 180.0(4) . . . . ? C17 C18 C19 C20 0.1(7) . . . . ? C18 C19 C20 C21 -0.5(6) . . . . ? C19 C20 C21 C16 -0.3(6) . . . . ? C19 C20 C21 C22 -177.3(4) . . . . ? C17 C16 C21 C20 1.4(6) . . . . ? N1 C16 C21 C20 -171.5(3) . . . . ? C17 C16 C21 C22 178.3(4) . . . . ? N1 C16 C21 C22 5.5(6) . . . . ? Cu1 O3 C24 N4 -179.8(3) . . . . ? C25 N4 C24 O3 -2.3(6) . . . . ? C26 N4 C24 O3 -179.2(4) . . . . ?