# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_m _database_code_depnum_ccdc_archive 'CCDC 827999' #TrackingRef 'neg_Cu.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H10 Cl2 Cu N4 O2' _chemical_formula_weight 304.62 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.4940(6) _cell_length_b 7.5099(4) _cell_length_c 22.6355(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2123.86(18) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1575 _cell_measurement_theta_min 3.1497 _cell_measurement_theta_max 27.5327 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.905 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 2.544 _exptl_absorpt_correction_T_min 0.89418 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction Ltd, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.4353 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4308 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0762 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1860 _reflns_number_gt 1214 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction Ltd, 2009)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction Ltd, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction Ltd, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0248P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1860 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0626 _refine_ls_wR_factor_gt 0.0601 _refine_ls_goodness_of_fit_ref 0.848 _refine_ls_restrained_S_all 0.848 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.24744(4) 0.20852(6) 0.295981(19) 0.01470(14) Uani 1 1 d . . . Cl1 Cl 0.07246(8) 0.24753(15) 0.32014(4) 0.0178(3) Uani 1 1 d . . . Cl2 Cl 0.21756(8) 0.00784(13) 0.22370(4) 0.0179(3) Uani 1 1 d . . . O1 O 0.28606(19) 0.3351(4) 0.36978(10) 0.0153(7) Uani 1 1 d . . . O2 O 0.4205(2) 0.4011(4) 0.43005(11) 0.0168(7) Uani 1 1 d . . . N4 N 0.1283(3) 0.4536(6) 0.45332(15) 0.0154(9) Uani 1 1 d . . . N1 N 0.4038(3) 0.1687(5) 0.29101(16) 0.0164(9) Uani 1 1 d . . . N2 N 0.1088(2) 0.5969(4) 0.54251(13) 0.0115(8) Uani 1 1 d . . . N3 N 0.2798(2) 0.5498(5) 0.50202(14) 0.0123(8) Uani 1 1 d . . . C1 C 0.3847(3) 0.3379(5) 0.38299(16) 0.0125(10) Uani 1 1 d . . . C2 C 0.4621(3) 0.2600(6) 0.33855(15) 0.0125(10) Uani 1 1 d . . . H2B H 0.5066 0.3564 0.3215 0.015 Uiso 1 1 calc R . . H2C H 0.5103 0.1746 0.3586 0.015 Uiso 1 1 calc R . . C3 C 0.1724(3) 0.5340(6) 0.49893(17) 0.0105(9) Uani 1 1 d . . . C4 C 0.1567(3) 0.6745(5) 0.58773(17) 0.0154(10) Uani 1 1 d . . . H4 H 0.1130 0.7192 0.6187 0.018 Uiso 1 1 calc R . . C5 C 0.2667(3) 0.6951(5) 0.59305(16) 0.0139(9) Uani 1 1 d . . . H5 H 0.2978 0.7533 0.6261 0.017 Uiso 1 1 calc R . . C6 C 0.3276(3) 0.6279(6) 0.54854(16) 0.0134(10) Uani 1 1 d . . . H6 H 0.4034 0.6360 0.5503 0.016 Uiso 1 1 calc R . . H1N1 H 0.421(4) 0.052(7) 0.2961(19) 0.050 Uiso 1 1 d . . . H1N2 H 0.418(4) 0.196(7) 0.2590(18) 0.050 Uiso 1 1 d . . . H4N1 H 0.063(4) 0.448(7) 0.4521(19) 0.050 Uiso 1 1 d . . . H4N2 H 0.164(3) 0.416(7) 0.429(2) 0.050 Uiso 1 1 d . . . H3N H 0.313(4) 0.506(7) 0.4771(19) 0.050 Uiso 1 1 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 0.0137(2) 0.0163(2) 0.0141(2) -0.0038(2) -0.0009(2) 0.0010(3) Cl1 0.0111(5) 0.0227(6) 0.0196(5) -0.0021(5) -0.0012(5) -0.0006(5) Cl2 0.0267(6) 0.0142(6) 0.0127(5) -0.0024(4) -0.0015(4) -0.0017(5) O1 0.0081(14) 0.0241(19) 0.0136(14) -0.0046(13) 0.0008(11) 0.0008(13) O2 0.0132(15) 0.0228(18) 0.0146(15) -0.0056(14) -0.0032(13) 0.0041(14) N4 0.0088(18) 0.023(2) 0.014(2) -0.0024(19) -0.0003(17) 0.001(2) N1 0.0176(19) 0.019(2) 0.0130(18) -0.002(2) -0.0020(17) 0.0003(18) N2 0.0089(18) 0.015(2) 0.0106(18) -0.0010(16) -0.0005(14) 0.0003(17) N3 0.011(2) 0.017(2) 0.0090(18) -0.0013(16) 0.0015(14) -0.0006(17) C1 0.013(2) 0.014(3) 0.011(2) 0.0013(19) 0.0023(18) 0.002(2) C2 0.013(2) 0.013(2) 0.011(2) -0.0030(19) 0.0032(17) 0.0002(19) C3 0.010(2) 0.012(2) 0.010(2) 0.006(2) 0.0005(17) 0.001(2) C4 0.019(2) 0.016(3) 0.012(2) 0.002(2) 0.0057(18) 0.002(2) C5 0.015(2) 0.014(2) 0.013(2) -0.0020(19) -0.0026(18) -0.003(2) C6 0.011(2) 0.015(2) 0.014(2) 0.004(2) -0.0044(19) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 1.980(4) . ? Cu1 O1 1.982(2) . ? Cu1 Cl2 2.2555(11) . ? Cu1 Cl1 2.2725(11) . ? O1 C1 1.269(4) . ? O2 C1 1.249(4) . ? N4 C3 1.317(5) . ? N4 H4N1 0.82(4) . ? N4 H4N2 0.77(5) . ? N1 C2 1.469(5) . ? N1 H1N1 0.91(5) . ? N1 H1N2 0.77(4) . ? N2 C4 1.321(4) . ? N2 C3 1.351(5) . ? N3 C6 1.345(5) . ? N3 C3 1.349(5) . ? N3 H3N 0.77(4) . ? C1 C2 1.513(5) . ? C2 H2B 0.9900 . ? C2 H2C 0.9900 . ? C4 C5 1.388(5) . ? C4 H4 0.9500 . ? C5 C6 1.360(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? 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 N1 Cu1 O1 83.12(13) . . ? N1 Cu1 Cl2 91.21(11) . . ? O1 Cu1 Cl2 166.49(8) . . ? N1 Cu1 Cl1 169.28(11) . . ? O1 Cu1 Cl1 88.25(7) . . ? Cl2 Cu1 Cl1 95.82(4) . . ? C1 O1 Cu1 116.3(2) . . ? C3 N4 H4N1 118(3) . . ? C3 N4 H4N2 119(4) . . ? H4N1 N4 H4N2 123(5) . . ? C2 N1 Cu1 112.1(2) . . ? C2 N1 H1N1 104(3) . . ? Cu1 N1 H1N1 111(3) . . ? C2 N1 H1N2 117(4) . . ? Cu1 N1 H1N2 104(4) . . ? H1N1 N1 H1N2 108(5) . . ? C4 N2 C3 117.0(3) . . ? C6 N3 C3 121.4(3) . . ? C6 N3 H3N 121(4) . . ? C3 N3 H3N 117(4) . . ? O2 C1 O1 123.7(4) . . ? O2 C1 C2 119.0(3) . . ? O1 C1 C2 117.3(3) . . ? N1 C2 C1 110.5(3) . . ? N1 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? C1 C2 H2C 109.5 . . ? H2B C2 H2C 108.1 . . ? N4 C3 N3 119.8(4) . . ? N4 C3 N2 119.1(3) . . ? N3 C3 N2 121.1(4) . . ? N2 C4 C5 124.4(4) . . ? N2 C4 H4 117.8 . . ? C5 C4 H4 117.8 . . ? C6 C5 C4 116.6(4) . . ? C6 C5 H5 121.7 . . ? C4 C5 H5 121.7 . . ? N3 C6 C5 119.6(3) . . ? N3 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N1 Cl1 0.91(5) 2.35(5) 3.244(4) 167(4) 8_655 N1 H1N2 Cl1 0.77(4) 2.66(4) 3.335(4) 147(4) 6_656 N4 H4N1 N2 0.82(4) 2.18(4) 2.988(5) 172(5) 5_566 N4 H4N2 O1 0.77(5) 2.12(4) 2.873(4) 169(5) . N3 H3N O2 0.77(4) 1.89(5) 2.645(4) 166(5) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.702 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.093 data_IRN10M _database_code_depnum_ccdc_archive 'CCDC 893821' #TrackingRef 'irn10mfull.cif' # 5. CRYSTAL DATA _chemical_compound_source ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C8 H7 Cu1 N3 O4' _chemical_formula_moiety 'C8 H7 Cu1 N3 O4' _chemical_formula_structural ? _chemical_formula_weight 272.70 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0366(7) _cell_length_b 9.1255(7) _cell_length_c 10.2985(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.832(5) _cell_angle_gamma 90.00 _cell_volume 938.35(12) _cell_measurement_reflns_used 8172 _cell_measurement_theta_min 6 _cell_measurement_theta_max 66 _cell_formula_units_z 4 _exptl_crystal_density_diffrn 1.930 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' loop_ _atom_type_symbol _atom_type_radius_bond Cu 1.17 O 0.73 N 0.75 C 0.77 H 0.32 _diffrn_radiation_type CU-K\a _diffrn_radiation_wavelength 1.54184 _exptl_absorpt_coefficient_mu 3.319 _cell_measurement_temperature 150(2) _exptl_crystal_F_000 548 # 6. DATA COLLECTION _diffrn_ambient_temperature 150(2) _diffrn_measurement_device_type Rigaku_Rapid_II _diffrn_radiation_monochromator 'confocal optics' _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.4867 _exptl_absorpt_correction_T_max 0.6284 _diffrn_reflns_number 7331 _diffrn_measured_fraction_theta_max 0.9970 _diffrn_reflns_theta_full 66.6 _diffrn_measured_fraction_theta_full 0.9970 _reflns_number_total 1650 _reflns_number_gt 1534 _reflns_threshold_expression >2.0\s(I) _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_theta_min 6.57 _diffrn_reflns_theta_max 66.64 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_max 12 _diffrn_special_details 'mosaicity from Denzo/Scalepack is 0.82' _diffrn_standards_number 0 _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_measurement_details ; Data were collected on a Rigaku Rapid which has a quarter chi circle and a 200 degree curved image plate at a fixed distance of 127.4mm. Strategy was optimized using the CrystalClear software. The completeness is the best that can be obtained with this geometry. Also the use of HKL2000/SCALEPACK lowers the number of observed data as inconsistent equivalents are removed from the data set and not included in the collected total ; # 7. REFINEMENT DATA _refine_special_details ; Outlier data were removed using a local program based on the method of Prince and Nicholson. Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.033 _refine_ls_R_factor_gt 0.031 _refine_ls_wR_factor_ref 0.084 _refine_ls_wR_factor_gt 0.083 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 1650 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_weighting_scheme 'calc ' _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.8705P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.32 _refine_diff_density_min -0.59 _refine_ls_extinction_method none _atom_type_scat_source 'International Tables for Crystallography (Vol C)' # 8. COMPUTING DATA _computing_data_collection 'CrystalClear(Rigaku, 2001)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1996)' _computing_structure_solution ; Direct methods (Charge Flipping, Oszlanyi and Suto, 2004 in PLATON, Spek, 1997) ; _computing_structure_refinement 'SHELX97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP (Johnson, 1976) PLATON (Spek, 1997) ; _computing_publication_material 'SHELX97(Sheldrick, 2008) and local programs' # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _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_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 0.08647(3) 0.17457(3) 0.23089(3) 0.01315(15) Uani 1 1 d . . . O1 -0.08026(16) 0.72155(19) 0.07455(15) 0.0173(4) Uani 1 1 d . . . O2 0.04483(18) 0.8053(2) -0.07585(16) 0.0228(4) Uani 1 1 d . . . O3 -0.00340(16) 0.48654(17) 0.23672(16) 0.0168(4) Uani 1 1 d . . . O4 0.17868(15) 0.35782(17) 0.20711(15) 0.0151(3) Uani 1 1 d . . . N11 0.27357(18) 0.0590(2) 0.24380(18) 0.0156(4) Uani 1 1 d . . . N12 0.3305(2) 0.1097(2) 0.0352(2) 0.0204(5) Uani 1 1 d . . . N13 0.4703(2) -0.0407(2) 0.1647(2) 0.0206(5) Uani 1 1 d . . . C1 0.0307(2) 0.7507(2) 0.0332(2) 0.0153(5) Uani 1 1 d . . . C2 0.1982(2) 0.6112(2) 0.1901(2) 0.0149(5) Uani 1 1 d . . . C3 0.1167(2) 0.4778(2) 0.2134(2) 0.0132(5) Uani 1 1 d . . . C12 0.3582(2) 0.0418(2) 0.1497(2) 0.0158(5) Uani 1 1 d . . . C14 0.4949(2) -0.1124(3) 0.2767(3) 0.0229(5) Uani 1 1 d . . . C15 0.4124(2) -0.1062(3) 0.3763(3) 0.0239(6) Uani 1 1 d . . . C16 0.3019(2) -0.0164(3) 0.3545(2) 0.0204(5) Uani 1 1 d . . . C511 0.1614(2) 0.7244(3) 0.1150(2) 0.0160(5) Uani 1 1 d . . . H2 0.2841 0.6146 0.2333 0.018 Uiso 1 1 calc R . . H14 0.5717 -0.1699 0.2889 0.027 Uiso 1 1 calc R . . H15 0.4303 -0.1594 0.4531 0.029 Uiso 1 1 calc R . . H16 0.2446 -0.0079 0.4196 0.024 Uiso 1 1 calc R . . H121 0.260(3) 0.151(3) 0.014(3) 0.023(8) Uiso 1 1 d . . . H122 0.379(3) 0.095(3) -0.026(3) 0.025(7) Uiso 1 1 d . . . H511 0.2252 0.7980 0.1123 0.019 Uiso 1 1 calc R . . 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 Cu1 0.0133(2) 0.0106(2) 0.0158(2) -0.00071(11) 0.00268(15) 0.00101(12) O1 0.0169(8) 0.0213(9) 0.0137(8) -0.0001(7) 0.0023(6) 0.0010(6) O2 0.0256(10) 0.0278(9) 0.0146(8) -0.0102(7) -0.0007(7) 0.0057(7) O3 0.0140(8) 0.0128(8) 0.0244(9) -0.0002(6) 0.0061(6) -0.0004(6) O4 0.0141(8) 0.0116(8) 0.0200(8) 0.0002(6) 0.0039(6) -0.0003(7) N11 0.0150(9) 0.0134(9) 0.0186(10) 0.0002(8) 0.0032(7) -0.0005(8) N12 0.0176(11) 0.0252(12) 0.0194(11) 0.0074(9) 0.0072(9) 0.0031(9) N13 0.0156(10) 0.0195(11) 0.0274(11) 0.0027(8) 0.0056(8) 0.0007(9) C1 0.0211(12) 0.0095(10) 0.0154(11) -0.0018(8) 0.0020(9) -0.0025(9) C2 0.0140(11) 0.0139(12) 0.0168(11) -0.0014(9) 0.0014(9) -0.0034(9) C3 0.0150(11) 0.0134(12) 0.0108(10) -0.0005(9) 0.0001(8) -0.0006(8) C12 0.0132(11) 0.0132(11) 0.0211(12) -0.0022(9) 0.0027(9) -0.0029(9) C14 0.0147(12) 0.0206(13) 0.0331(14) 0.0024(9) 0.0016(10) 0.0036(11) C15 0.0227(13) 0.0257(14) 0.0228(13) 0.0022(10) -0.0003(10) 0.0076(11) C16 0.0201(13) 0.0208(13) 0.0207(12) 0.0004(9) 0.0038(10) 0.0030(10) C511 0.0169(12) 0.0147(12) 0.0169(11) -0.0040(9) 0.0047(9) -0.0035(9) # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.9388(16) . . ? Cu1 O3 1.9512(16) . 2_545 ? Cu1 O2 1.9728(18) . 3_565 ? Cu1 O1 2.0562(16) . 2_545 ? Cu1 N11 2.1462(19) . . ? O1 C1 1.260(3) . . ? O1 Cu1 2.0562(16) . 2_555 ? O2 C1 1.250(3) . . ? O2 Cu1 1.9728(18) . 3_565 ? O3 C3 1.256(3) . . ? O3 Cu1 1.9512(16) . 2_555 ? O4 C3 1.264(3) . . ? N11 C16 1.337(3) . . ? N11 C12 1.361(3) . . ? N12 C12 1.335(3) . . ? N12 H121 0.81(3) . . ? N12 H122 0.85(3) . . ? N13 C14 1.328(3) . . ? N13 C12 1.350(3) . . ? C1 C511 1.505(3) . . ? C2 C511 1.320(3) . . ? C2 C3 1.500(3) . . ? C2 H2 0.9300 . . ? C14 C15 1.383(4) . . ? C14 H14 0.9300 . . ? C15 C16 1.379(3) . . ? C15 H15 0.9300 . . ? C16 H16 0.9300 . . ? C511 H511 0.9300 . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O3 176.23(7) . . 2_545 ? O4 Cu1 O2 96.07(7) . . 3_565 ? O3 Cu1 O2 87.60(7) 2_545 . 3_565 ? O4 Cu1 O1 90.31(7) . . 2_545 ? O3 Cu1 O1 87.76(7) 2_545 . 2_545 ? O2 Cu1 O1 133.27(7) 3_565 . 2_545 ? O4 Cu1 N11 90.34(7) . . . ? O3 Cu1 N11 86.76(7) 2_545 . . ? O2 Cu1 N11 127.17(7) 3_565 . . ? O1 Cu1 N11 98.92(7) 2_545 . . ? C1 O1 Cu1 119.25(14) . . 2_555 ? C1 O2 Cu1 129.54(15) . . 3_565 ? C3 O3 Cu1 121.60(14) . . 2_555 ? C3 O4 Cu1 119.80(14) . . . ? C16 N11 C12 117.0(2) . . . ? C16 N11 Cu1 114.50(15) . . . ? C12 N11 Cu1 128.17(15) . . . ? C12 N12 H121 123(2) . . . ? C12 N12 H122 120(2) . . . ? H121 N12 H122 116(3) . . . ? C14 N13 C12 116.9(2) . . . ? O2 C1 O1 124.9(2) . . . ? O2 C1 C511 113.2(2) . . . ? O1 C1 C511 121.8(2) . . . ? C511 C2 C3 127.2(2) . . . ? C511 C2 H2 116.40 . . . ? C3 C2 H2 116.40 . . . ? O3 C3 O4 123.5(2) . . . ? O3 C3 C2 121.9(2) . . . ? O4 C3 C2 114.58(19) . . . ? N12 C12 N13 117.1(2) . . . ? N12 C12 N11 119.1(2) . . . ? N13 C12 N11 123.8(2) . . . ? N13 C14 C15 123.5(2) . . . ? N13 C14 H14 118.20 . . . ? C15 C14 H14 118.20 . . . ? C16 C15 C14 115.8(2) . . . ? C16 C15 H15 122.10 . . . ? C14 C15 H15 122.10 . . . ? N11 C16 C15 122.9(2) . . . ? N11 C16 H16 118.60 . . . ? C15 C16 H16 118.60 . . . ? C2 C511 C1 129.0(2) . . . ? C2 C511 H511 115.50 . . . ? C1 C511 H511 115.50 . . . ? 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 O3 Cu1 O4 C3 -129.2(9) 2_545 . . . ? O2 Cu1 O4 C3 63.64(17) 3_565 . . . ? O1 Cu1 O4 C3 -69.98(17) 2_545 . . . ? N11 Cu1 O4 C3 -168.90(16) . . . . ? O4 Cu1 N11 C16 122.28(17) . . . . ? O3 Cu1 N11 C16 -55.31(17) 2_545 . . . ? O2 Cu1 N11 C16 -139.83(16) 3_565 . . . ? O1 Cu1 N11 C16 31.91(17) 2_545 . . . ? O4 Cu1 N11 C12 -64.79(19) . . . . ? O3 Cu1 N11 C12 117.62(19) 2_545 . . . ? O2 Cu1 N11 C12 33.1(2) 3_565 . . . ? O1 Cu1 N11 C12 -155.16(19) 2_545 . . . ? Cu1 O2 C1 O1 -14.5(4) 3_565 . . . ? Cu1 O2 C1 C511 166.68(15) 3_565 . . . ? Cu1 O1 C1 O2 -166.80(18) 2 . . . ? Cu1 O1 C1 C511 12.0(3) 2 . . . ? Cu1 O3 C3 O4 171.40(16) 2 . . . ? Cu1 O3 C3 C2 -8.9(3) 2 . . . ? Cu1 O4 C3 O3 1.2(3) . . . . ? Cu1 O4 C3 C2 -178.56(14) . . . . ? C511 C2 C3 O3 -45.5(3) . . . . ? C511 C2 C3 O4 134.3(2) . . . . ? C14 N13 C12 N12 -177.5(2) . . . . ? C14 N13 C12 N11 2.5(3) . . . . ? C16 N11 C12 N12 177.0(2) . . . . ? Cu1 N11 C12 N12 4.2(3) . . . . ? C16 N11 C12 N13 -3.0(3) . . . . ? Cu1 N11 C12 N13 -175.82(17) . . . . ? C12 N13 C14 C15 0.0(4) . . . . ? N13 C14 C15 C16 -1.7(4) . . . . ? C12 N11 C16 C15 1.1(3) . . . . ? Cu1 N11 C16 C15 174.9(2) . . . . ? C14 C15 C16 N11 1.1(4) . . . . ? C3 C2 C511 C1 -0.2(4) . . . . ? O2 C1 C511 C2 -139.1(2) . . . . ? O1 C1 C511 C2 42.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N12 H122 N13 0.853 2.24(3) 3.077(4) 171(3) . 3_655 ? data_z2 _database_code_depnum_ccdc_archive 'CCDC 893822' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 Cu N6 O6' _chemical_formula_sum 'C22 H20 Cu N6 O6' _chemical_formula_weight 527.98 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9258(2) _cell_length_b 12.0698(3) _cell_length_c 20.1039(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.815(3) _cell_angle_gamma 90.00 _cell_volume 2386.13(10) _cell_formula_units_Z 4 _cell_measurement_temperature 294.0(1) _cell_measurement_reflns_used 4909 _cell_measurement_theta_min 2.96? _cell_measurement_theta_max 28.91 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.4 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 294.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1544 _diffrn_standards_number 20051 _diffrn_standards_interval_count 4 _diffrn_standards_interval_time '60 min' _diffrn_standards_decay_% ? _diffrn_reflns_number 19534 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 28.91 _reflns_number_total 5614 _reflns_number_gt 3757 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.4 ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.4 ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.4 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.8454P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5614 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.0960 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.68146(3) 0.18304(3) 0.645879(17) 0.03490(12) Uani 1 1 d . . . O1 O 0.64434(18) 0.10859(17) 0.72869(10) 0.0415(5) Uani 1 1 d . . . O2 O 0.7853(2) 0.24533(18) 0.76133(11) 0.0524(6) Uani 1 1 d . . . C1 C 0.7178(3) 0.1653(2) 0.77516(15) 0.0376(7) Uani 1 1 d . . . C2 C 0.7158(3) 0.1276(2) 0.84500(14) 0.0363(6) Uani 1 1 d . . . O3 O 0.5473(2) -0.01396(18) 0.81365(12) 0.0583(6) Uani 1 1 d . . . H3 H 0.5677 0.0244 0.7727 0.076 Uiso 1 1 d R . . C3 C 0.6308(3) 0.0419(2) 0.86068(16) 0.0430(7) Uani 1 1 d . . . C4 C 0.6311(4) 0.0122(3) 0.92711(19) 0.0692(11) Uani 1 1 d . . . H4 H 0.5744 -0.0444 0.9380 0.083 Uiso 1 1 calc R . . C5 C 0.7135(5) 0.0650(4) 0.9765(2) 0.0925(15) Uani 1 1 d . . . H5 H 0.7126 0.0443 1.0210 0.111 Uiso 1 1 calc R . . C6 C 0.7982(5) 0.1487(4) 0.9616(2) 0.0889(14) Uani 1 1 d . . . H6 H 0.8547 0.1842 0.9957 0.107 Uiso 1 1 calc R . . C7 C 0.7987(4) 0.1791(3) 0.89694(17) 0.0576(9) Uani 1 1 d . . . H7 H 0.8562 0.2359 0.8871 0.069 Uiso 1 1 calc R . . O11 O 0.71829(19) 0.25003(16) 0.56205(10) 0.0408(5) Uani 1 1 d . . . O12 O 0.5770(2) 0.11400(17) 0.52720(10) 0.0481(5) Uani 1 1 d . . . C11 C 0.6563(3) 0.1905(2) 0.51551(15) 0.0357(6) Uani 1 1 d . . . C12 C 0.6803(3) 0.2133(2) 0.44570(14) 0.0320(6) Uani 1 1 d . . . O13 O 0.51180(19) 0.07993(16) 0.40063(10) 0.0462(5) Uani 1 1 d . . . H13 H 0.5094 0.0813 0.4501 0.060 Uiso 1 1 d R . . C13 C 0.6061(3) 0.1578(2) 0.39189(15) 0.0367(7) Uani 1 1 d . . . C14 C 0.6276(3) 0.1828(3) 0.32694(16) 0.0522(8) Uani 1 1 d . . . H14 H 0.5757 0.1485 0.2907 0.063 Uiso 1 1 calc R . . C15 C 0.7256(4) 0.2582(3) 0.31599(17) 0.0557(9) Uani 1 1 d . . . H15 H 0.7392 0.2747 0.2722 0.067 Uiso 1 1 calc R . . C16 C 0.8041(3) 0.3100(3) 0.36872(17) 0.0497(8) Uani 1 1 d . . . H16 H 0.8723 0.3592 0.3608 0.060 Uiso 1 1 calc R . . C17 C 0.7805(3) 0.2880(2) 0.43300(15) 0.0391(7) Uani 1 1 d . . . H17 H 0.8323 0.3236 0.4687 0.047 Uiso 1 1 calc R . . N21 N 0.8449(2) 0.08774(19) 0.64260(12) 0.0388(6) Uani 1 1 d . . . N22 N 0.9947(2) 0.2351(2) 0.65463(14) 0.0521(7) Uani 1 1 d . . . H22A H 1.0777 0.2569 0.6609 0.063 Uiso 1 1 d R . . H22B H 0.9306 0.2686 0.6810 0.063 Uiso 1 1 d R . . C22 C 0.9709(3) 0.1292(2) 0.64089(15) 0.0398(7) Uani 1 1 d . . . N23 N 1.0747(2) 0.0692(2) 0.62448(17) 0.0644(9) Uani 1 1 d . . . C24 C 1.0505(4) -0.0365(3) 0.6117(3) 0.1030(18) Uani 1 1 d . . . H24 H 1.1204 -0.0797 0.5991 0.124 Uiso 1 1 calc R . . C25 C 0.9268(4) -0.0866(3) 0.6160(3) 0.1011(18) Uani 1 1 d . . . H25 H 0.9131 -0.1621 0.6085 0.121 Uiso 1 1 calc R . . C26 C 0.8270(3) -0.0196(3) 0.6316(2) 0.0650(11) Uani 1 1 d . . . H26 H 0.7421 -0.0502 0.6348 0.078 Uiso 1 1 calc R . . N31 N 0.5231(2) 0.28376(19) 0.65021(12) 0.0378(6) Uani 1 1 d . . . N32 N 0.3624(2) 0.1463(2) 0.63134(15) 0.0584(8) Uani 1 1 d . . . H32A H 0.2755 0.1251 0.6308 0.070 Uiso 1 1 d R . . H32B H 0.4198 0.0987 0.6116 0.070 Uiso 1 1 d R . . C32 C 0.3924(3) 0.2505(2) 0.64600(14) 0.0366(7) Uani 1 1 d . . . N33 N 0.2896(2) 0.3179(2) 0.65746(13) 0.0433(6) Uani 1 1 d . . . C34 C 0.3205(3) 0.4213(3) 0.67196(19) 0.0578(9) Uani 1 1 d . . . H34 H 0.2512 0.4687 0.6807 0.069 Uiso 1 1 calc R . . C35 C 0.4502(4) 0.4640(3) 0.6750(2) 0.0756(13) Uani 1 1 d . . . H35 H 0.4692 0.5383 0.6841 0.091 Uiso 1 1 calc R . . C36 C 0.5486(3) 0.3904(3) 0.6637(2) 0.0602(10) Uani 1 1 d . . . H36 H 0.6375 0.4157 0.6656 0.072 Uiso 1 1 calc R . . 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 0.02207(17) 0.0455(2) 0.0383(2) 0.00109(17) 0.00854(13) -0.00178(15) O1 0.0374(11) 0.0481(12) 0.0397(12) -0.0011(10) 0.0077(9) -0.0081(9) O2 0.0518(13) 0.0532(14) 0.0539(14) 0.0039(11) 0.0132(11) -0.0162(11) C1 0.0303(14) 0.0423(18) 0.0414(17) 0.0007(14) 0.0097(13) 0.0035(13) C2 0.0340(15) 0.0357(16) 0.0391(17) 0.0021(13) 0.0054(13) 0.0074(13) O3 0.0687(15) 0.0546(14) 0.0529(14) 0.0030(11) 0.0125(12) -0.0257(12) C3 0.0462(17) 0.0386(17) 0.0456(19) 0.0053(15) 0.0110(15) 0.0053(14) C4 0.085(3) 0.065(2) 0.057(3) 0.022(2) 0.008(2) -0.011(2) C5 0.128(4) 0.100(4) 0.046(3) 0.019(2) -0.001(3) -0.020(3) C6 0.108(4) 0.099(3) 0.051(3) 0.004(2) -0.019(2) -0.025(3) C7 0.061(2) 0.060(2) 0.049(2) 0.0021(18) -0.0007(17) -0.0102(18) O11 0.0364(11) 0.0493(13) 0.0376(12) -0.0011(10) 0.0084(9) -0.0078(9) O12 0.0479(12) 0.0486(13) 0.0508(13) 0.0015(10) 0.0171(10) -0.0160(10) C11 0.0295(14) 0.0368(16) 0.0416(17) 0.0034(14) 0.0080(13) 0.0024(12) C12 0.0271(13) 0.0329(15) 0.0371(16) 0.0013(12) 0.0080(12) 0.0038(11) O13 0.0400(11) 0.0476(13) 0.0503(13) -0.0040(10) 0.0035(10) -0.0127(9) C13 0.0337(15) 0.0337(16) 0.0427(18) -0.0009(13) 0.0049(13) 0.0028(12) C14 0.062(2) 0.056(2) 0.0371(18) -0.0051(16) 0.0002(16) -0.0056(18) C15 0.071(2) 0.060(2) 0.039(2) 0.0050(17) 0.0173(18) -0.0017(19) C16 0.0521(19) 0.0435(18) 0.058(2) 0.0055(16) 0.0222(17) -0.0067(15) C17 0.0378(16) 0.0370(16) 0.0432(18) -0.0010(13) 0.0078(14) -0.0031(12) N21 0.0242(11) 0.0421(15) 0.0506(16) 0.0009(12) 0.0068(11) -0.0029(10) N22 0.0244(12) 0.0508(17) 0.083(2) -0.0261(15) 0.0120(13) -0.0065(11) C22 0.0245(14) 0.0425(18) 0.053(2) -0.0007(15) 0.0056(13) 0.0012(12) N23 0.0280(13) 0.0419(16) 0.127(3) -0.0133(17) 0.0253(15) -0.0015(12) C24 0.043(2) 0.049(2) 0.224(6) -0.028(3) 0.041(3) 0.0059(18) C25 0.046(2) 0.038(2) 0.223(6) -0.016(3) 0.033(3) -0.0059(17) C26 0.0316(17) 0.047(2) 0.119(3) 0.003(2) 0.0172(19) -0.0041(15) N31 0.0255(12) 0.0403(14) 0.0495(16) 0.0042(11) 0.0115(11) -0.0025(10) N32 0.0269(13) 0.0482(17) 0.103(2) -0.0279(16) 0.0180(14) -0.0040(11) C32 0.0267(14) 0.0451(18) 0.0392(17) 0.0018(14) 0.0089(13) 0.0003(12) N33 0.0302(12) 0.0417(15) 0.0606(17) 0.0035(13) 0.0156(11) 0.0058(11) C34 0.0429(19) 0.045(2) 0.089(3) 0.0088(18) 0.0233(18) 0.0116(15) C35 0.056(2) 0.0341(19) 0.141(4) -0.004(2) 0.027(2) -0.0012(16) C36 0.0369(17) 0.045(2) 0.101(3) 0.0046(19) 0.0205(18) -0.0099(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O11 1.9482(19) . ? Cu1 O1 1.9701(19) . ? Cu1 N21 1.997(2) . ? Cu1 N31 1.998(2) . ? O1 C1 1.299(3) . ? O2 C1 1.229(3) . ? C1 C2 1.479(4) . ? C2 C7 1.386(4) . ? C2 C3 1.398(4) . ? O3 C3 1.349(4) . ? O3 H3 0.9889 . ? C3 C4 1.382(4) . ? C4 C5 1.356(5) . ? C4 H4 0.9300 . ? C5 C6 1.373(6) . ? C5 H5 0.9300 . ? C6 C7 1.351(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? O11 C11 1.270(3) . ? O12 C11 1.256(3) . ? C11 C12 1.481(4) . ? C12 C17 1.392(4) . ? C12 C13 1.394(4) . ? O13 C13 1.354(3) . ? O13 H13 0.9990 . ? C13 C14 1.385(4) . ? C14 C15 1.371(4) . ? C14 H14 0.9300 . ? C15 C16 1.377(4) . ? C15 H15 0.9300 . ? C16 C17 1.370(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N21 C26 1.322(4) . ? N21 C22 1.353(3) . ? N22 C22 1.322(4) . ? N22 H22A 0.8575 . ? N22 H22B 0.9702 . ? C22 N23 1.337(4) . ? N23 C24 1.317(4) . ? C24 C25 1.382(5) . ? C24 H24 0.9300 . ? C25 C26 1.348(5) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? N31 C36 1.333(4) . ? N31 C32 1.350(3) . ? N32 C32 1.317(4) . ? N32 H32A 0.8984 . ? N32 H32B 0.9344 . ? C32 N33 1.349(3) . ? N33 C34 1.308(4) . ? C34 C35 1.381(5) . ? C34 H34 0.9300 . ? C35 C36 1.361(5) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? 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 O11 Cu1 O1 177.38(8) . . ? O11 Cu1 N21 87.80(9) . . ? O1 Cu1 N21 90.64(9) . . ? O11 Cu1 N31 91.52(9) . . ? O1 Cu1 N31 90.12(9) . . ? N21 Cu1 N31 177.61(9) . . ? C1 O1 Cu1 102.48(17) . . ? O2 C1 O1 121.4(3) . . ? O2 C1 C2 122.3(3) . . ? O1 C1 C2 116.2(3) . . ? C7 C2 C3 118.5(3) . . ? C7 C2 C1 119.6(3) . . ? C3 C2 C1 121.9(3) . . ? C3 O3 H3 100.0 . . ? O3 C3 C4 117.9(3) . . ? O3 C3 C2 122.9(3) . . ? C4 C3 C2 119.2(3) . . ? C5 C4 C3 120.5(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.8(4) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 119.5(4) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C2 121.6(3) . . ? C6 C7 H7 119.2 . . ? C2 C7 H7 119.2 . . ? C11 O11 Cu1 105.86(17) . . ? O12 C11 O11 122.1(3) . . ? O12 C11 C12 120.0(3) . . ? O11 C11 C12 118.0(2) . . ? C17 C12 C13 119.0(3) . . ? C17 C12 C11 120.3(3) . . ? C13 C12 C11 120.7(2) . . ? C13 O13 H13 103.2 . . ? O13 C13 C14 118.2(3) . . ? O13 C13 C12 122.3(3) . . ? C14 C13 C12 119.6(3) . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 121.1(3) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 119.1(3) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C12 121.1(3) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? C26 N21 C22 117.5(2) . . ? C26 N21 Cu1 118.63(19) . . ? C22 N21 Cu1 123.09(19) . . ? C22 N22 H22A 117.9 . . ? C22 N22 H22B 113.9 . . ? H22A N22 H22B 118.7 . . ? N22 C22 N23 117.0(3) . . ? N22 C22 N21 119.5(3) . . ? N23 C22 N21 123.5(3) . . ? C24 N23 C22 116.6(3) . . ? N23 C24 C25 123.5(3) . . ? N23 C24 H24 118.3 . . ? C25 C24 H24 118.3 . . ? C26 C25 C24 116.0(3) . . ? C26 C25 H25 122.0 . . ? C24 C25 H25 122.0 . . ? N21 C26 C25 122.8(3) . . ? N21 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? C36 N31 C32 117.0(2) . . ? C36 N31 Cu1 117.90(19) . . ? C32 N31 Cu1 124.88(19) . . ? C32 N32 H32A 117.5 . . ? C32 N32 H32B 123.4 . . ? H32A N32 H32B 117.4 . . ? N32 C32 N33 117.4(2) . . ? N32 C32 N31 118.9(2) . . ? N33 C32 N31 123.6(3) . . ? C34 N33 C32 116.9(2) . . ? N33 C34 C35 123.7(3) . . ? N33 C34 H34 118.1 . . ? C35 C34 H34 118.1 . . ? C36 C35 C34 115.8(3) . . ? C36 C35 H35 122.1 . . ? C34 C35 H35 122.1 . . ? N31 C36 C35 122.9(3) . . ? N31 C36 H36 118.5 . . ? C35 C36 H36 118.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.99 1.61 2.546(3) 157.1 . O13 H13 O12 1.00 1.65 2.572(3) 151.3 . N22 H22A N33 0.86 2.24 3.086(3) 169.8 1_655 N22 H22B O2 0.97 2.32 3.185(3) 147.6 . N32 H32A N23 0.90 2.09 2.989(3) 176.3 1_455 N32 H32B O13 0.93 2.28 3.106(3) 146.5 3_656 N32 H32B O12 0.93 2.46 3.208(3) 136.5 . _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.592 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.059 data_z2_2 _database_code_depnum_ccdc_archive 'CCDC 893823' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 Cu N6 O6, 4(C7 H6 O3), 2(C4 H5 N3)' _chemical_formula_sum 'C58 H54 Cu N12 O18' _chemical_formula_weight 1270.67 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6075(2) _cell_length_b 9.9472(4) _cell_length_c 20.8858(8) _cell_angle_alpha 81.235(3) _cell_angle_beta 82.268(3) _cell_angle_gamma 72.818(3) _cell_volume 1485.61(9) _cell_formula_units_Z 1 _cell_measurement_temperature 295.5(1) _cell_measurement_reflns_used 18500 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 30.71 _exptl_crystal_description block _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 659 _exptl_absorpt_coefficient_mu 0.451 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.4 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295.5(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1544 _diffrn_standards_number 49148 _diffrn_standards_interval_count 4 _diffrn_standards_interval_time '60 min' _diffrn_standards_decay_% ? _diffrn_reflns_number 49147 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 30.71 _reflns_number_total 8488 _reflns_number_gt 7540 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.4 ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.4 ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.4 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.4368P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8488 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.5000 0.0000 0.5000 0.02814(7) Uani 1 2 d S . . O1 O 0.42628(13) 0.11489(10) 0.41627(5) 0.03321(19) Uani 1 1 d . . . O2 O 0.19639(14) 0.02768(10) 0.45896(5) 0.0394(2) Uani 1 1 d . . . C1 C 0.26196(17) 0.11052(12) 0.41719(6) 0.0280(2) Uani 1 1 d . . . C2 C 0.14048(16) 0.20836(12) 0.36981(6) 0.0261(2) Uani 1 1 d . . . O3 O -0.11255(14) 0.11137(11) 0.41219(5) 0.0394(2) Uani 1 1 d . . . H3 H -0.0185 0.0672 0.4368 0.051 Uiso 1 1 d R . . C3 C -0.04232(17) 0.20404(13) 0.37006(6) 0.0282(2) Uani 1 1 d . . . C4 C -0.15743(19) 0.29713(16) 0.32666(7) 0.0394(3) Uani 1 1 d . . . H4 H -0.2780 0.2933 0.3265 0.047 Uiso 1 1 calc R . . C5 C -0.0929(2) 0.39497(19) 0.28390(8) 0.0487(4) Uani 1 1 d . . . H5 H -0.1708 0.4576 0.2551 0.058 Uiso 1 1 calc R . . C6 C 0.0864(2) 0.40152(18) 0.28314(8) 0.0479(4) Uani 1 1 d . . . H6 H 0.1285 0.4684 0.2541 0.058 Uiso 1 1 calc R . . C7 C 0.20267(19) 0.30843(15) 0.32566(7) 0.0357(3) Uani 1 1 d . . . H7 H 0.3235 0.3125 0.3249 0.043 Uiso 1 1 calc R . . N11 N 0.37805(16) 0.17671(10) 0.54280(5) 0.0307(2) Uani 1 1 d . . . N12 N 0.58329(19) 0.29961(13) 0.49264(8) 0.0523(4) Uani 1 1 d . . . H12A H 0.6130 0.3801 0.4828 0.063 Uiso 1 1 d R . . H12B H 0.6548 0.2258 0.4826 0.063 Uiso 1 1 d R . . C12 C 0.42384(18) 0.30002(12) 0.52666(7) 0.0317(3) Uani 1 1 d . . . N13 N 0.31511(18) 0.42570(12) 0.54358(7) 0.0427(3) Uani 1 1 d . . . C14 C 0.1593(2) 0.42548(17) 0.57954(10) 0.0547(4) Uani 1 1 d . . . H14 H 0.0806 0.5116 0.5905 0.066 Uiso 1 1 calc R . . C15 C 0.1071(3) 0.3037(2) 0.60174(11) 0.0618(5) Uani 1 1 d . . . H15 H -0.0003 0.3051 0.6291 0.074 Uiso 1 1 calc R . . C16 C 0.2220(2) 0.18085(16) 0.58129(8) 0.0444(3) Uani 1 1 d . . . H16 H 0.1902 0.0969 0.5947 0.053 Uiso 1 1 calc R . . O21 O 0.6641(2) -0.23800(16) 0.07074(7) 0.0720(4) Uani 1 1 d . . . O22 O 0.8183(2) -0.35153(14) 0.15408(6) 0.0643(4) Uani 1 1 d . . . H22 H 0.8416 -0.4244 0.1323 0.084 Uiso 1 1 d R . . C21 C 0.7223(2) -0.23717(19) 0.12259(8) 0.0496(4) Uani 1 1 d . . . C22 C 0.6877(2) -0.10577(19) 0.15238(8) 0.0482(4) Uani 1 1 d . . . O23 O 0.5663(3) 0.03584(19) 0.05585(8) 0.1058(7) Uani 1 1 d . . . H23 H 0.5877 -0.0611 0.0479 0.138 Uiso 1 1 d R . . C23 C 0.6128(3) 0.0251(2) 0.11696(10) 0.0622(5) Uani 1 1 d . . . C24 C 0.5833(4) 0.1496(2) 0.14431(12) 0.0749(6) Uani 1 1 d . . . H26 H 0.5356 0.2368 0.1204 0.090 Uiso 1 1 calc R . . C25 C 0.6248(4) 0.1436(3) 0.20666(13) 0.0780(7) Uani 1 1 d . . . H25 H 0.6044 0.2271 0.2250 0.094 Uiso 1 1 calc R . . C26 C 0.6961(4) 0.0156(3) 0.24231(12) 0.0851(8) Uani 1 1 d . . . H56 H 0.7219 0.0124 0.2849 0.102 Uiso 1 1 calc R . . C27 C 0.7291(3) -0.1077(2) 0.21510(10) 0.0678(5) Uani 1 1 d . . . H27 H 0.7802 -0.1940 0.2392 0.081 Uiso 1 1 calc R . . O31 O 0.3346(2) 0.56711(14) 0.12042(7) 0.0637(4) Uani 1 1 d . . . O32 O 0.1723(2) 0.79102(14) 0.09639(7) 0.0656(4) Uani 1 1 d . . . H32 H 0.1560 0.7612 0.0603 0.085 Uiso 1 1 d R . . C31 C 0.2669(3) 0.68884(18) 0.13518(9) 0.0497(4) Uani 1 1 d . . . C32 C 0.2899(2) 0.72671(17) 0.19839(8) 0.0460(3) Uani 1 1 d . . . O33 O 0.48907(18) 0.49412(14) 0.22824(8) 0.0625(3) Uani 1 1 d . . . H33 H 0.4514 0.4956 0.1890 0.081 Uiso 1 1 d R . . C33 C 0.4005(2) 0.62733(19) 0.24175(9) 0.0487(4) Uani 1 1 d . . . C34 C 0.4197(3) 0.6636(3) 0.30154(11) 0.0653(5) Uani 1 1 d . . . H34 H 0.4924 0.5972 0.3307 0.078 Uiso 1 1 calc R . . C35 C 0.3320(3) 0.7965(3) 0.31751(12) 0.0753(6) Uani 1 1 d . . . H35 H 0.3469 0.8205 0.3574 0.090 Uiso 1 1 calc R . . C36 C 0.2217(4) 0.8957(2) 0.27558(12) 0.0754(6) Uani 1 1 d . . . H36 H 0.1619 0.9858 0.2872 0.090 Uiso 1 1 calc R . . C37 C 0.2002(3) 0.8611(2) 0.21647(10) 0.0612(5) Uani 1 1 d . . . H37 H 0.1250 0.9281 0.1882 0.073 Uiso 1 1 calc R . . N41 N -0.0934(2) 0.27456(18) 0.01202(8) 0.0591(4) Uani 1 1 d . . . N42 N -0.2822(3) 0.5021(2) 0.00993(9) 0.0680(5) Uani 1 1 d . . . H42A H -0.3135 0.5850 0.0237 0.082 Uiso 1 1 d R . . H42B H -0.3150 0.4935 -0.0278 0.082 Uiso 1 1 d R . . C42 C -0.1551(3) 0.3974(2) 0.03862(9) 0.0518(4) Uani 1 1 d . . . N43 N -0.0935(2) 0.41895(18) 0.09266(8) 0.0592(4) Uani 1 1 d . . . C44 C 0.0388(4) 0.3135(3) 0.11890(11) 0.0717(6) Uani 1 1 d . . . H44 H 0.0856 0.3269 0.1556 0.086 Uiso 1 1 calc R . . C45 C 0.1095(4) 0.1861(3) 0.09468(12) 0.0754(6) Uani 1 1 d . . . H45 H 0.2020 0.1135 0.1139 0.090 Uiso 1 1 calc R . . C46 C 0.0368(3) 0.1716(2) 0.04074(11) 0.0693(5) Uani 1 1 d . . . H46 H 0.0802 0.0859 0.0233 0.083 Uiso 1 1 calc R . . 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 0.03378(12) 0.01596(9) 0.03539(12) 0.00020(7) -0.01314(8) -0.00535(7) O1 0.0301(4) 0.0301(4) 0.0386(5) 0.0015(4) -0.0113(4) -0.0066(4) O2 0.0407(5) 0.0329(5) 0.0422(5) 0.0121(4) -0.0106(4) -0.0119(4) C1 0.0312(6) 0.0232(5) 0.0287(5) -0.0031(4) -0.0067(4) -0.0045(4) C2 0.0276(5) 0.0240(5) 0.0256(5) -0.0026(4) -0.0051(4) -0.0046(4) O3 0.0334(5) 0.0340(5) 0.0521(6) 0.0044(4) -0.0071(4) -0.0149(4) C3 0.0289(6) 0.0256(5) 0.0304(6) -0.0051(4) -0.0045(4) -0.0066(4) C4 0.0307(6) 0.0458(8) 0.0405(7) -0.0013(6) -0.0120(5) -0.0068(6) C5 0.0441(8) 0.0546(9) 0.0394(8) 0.0127(7) -0.0168(6) -0.0049(7) C6 0.0454(8) 0.0508(9) 0.0397(8) 0.0189(7) -0.0067(6) -0.0123(7) C7 0.0307(6) 0.0389(7) 0.0350(7) 0.0051(5) -0.0040(5) -0.0103(5) N11 0.0379(6) 0.0199(4) 0.0366(5) -0.0012(4) -0.0070(4) -0.0110(4) N12 0.0425(7) 0.0252(5) 0.0889(11) -0.0187(6) 0.0207(7) -0.0149(5) C12 0.0344(6) 0.0210(5) 0.0413(7) -0.0066(5) -0.0011(5) -0.0098(5) N13 0.0441(7) 0.0229(5) 0.0610(8) -0.0127(5) 0.0103(6) -0.0121(5) C14 0.0507(9) 0.0365(8) 0.0769(12) -0.0257(8) 0.0209(8) -0.0148(7) C15 0.0591(10) 0.0526(10) 0.0783(13) -0.0265(9) 0.0324(10) -0.0305(9) C16 0.0559(9) 0.0358(7) 0.0483(8) -0.0067(6) 0.0051(7) -0.0269(7) O21 0.0922(11) 0.0624(8) 0.0560(8) -0.0179(7) -0.0264(7) 0.0004(8) O22 0.0979(11) 0.0440(7) 0.0508(7) -0.0021(5) -0.0198(7) -0.0160(7) C21 0.0530(9) 0.0521(9) 0.0423(8) -0.0055(7) -0.0023(7) -0.0137(7) C22 0.0497(9) 0.0496(9) 0.0450(8) -0.0066(7) -0.0043(7) -0.0131(7) O23 0.165(2) 0.0654(10) 0.0652(10) -0.0116(8) -0.0513(11) 0.0210(11) C23 0.0705(12) 0.0557(10) 0.0524(10) -0.0089(8) -0.0133(9) -0.0007(9) C24 0.0902(16) 0.0502(11) 0.0754(14) -0.0085(10) -0.0189(12) -0.0006(11) C25 0.0966(17) 0.0568(12) 0.0827(15) -0.0240(11) -0.0205(13) -0.0116(12) C26 0.127(2) 0.0673(14) 0.0658(13) -0.0175(11) -0.0356(14) -0.0185(14) C27 0.0952(16) 0.0555(11) 0.0545(11) -0.0040(9) -0.0237(11) -0.0179(11) O31 0.0759(9) 0.0485(7) 0.0636(8) -0.0230(6) -0.0108(7) -0.0029(6) O32 0.0901(10) 0.0491(7) 0.0528(7) -0.0136(6) -0.0143(7) -0.0051(7) C31 0.0538(9) 0.0446(8) 0.0500(9) -0.0123(7) 0.0001(7) -0.0118(7) C32 0.0475(8) 0.0422(8) 0.0495(9) -0.0127(7) 0.0023(7) -0.0137(7) O33 0.0536(7) 0.0495(7) 0.0825(10) -0.0140(7) -0.0187(7) -0.0030(6) C33 0.0393(8) 0.0489(9) 0.0608(10) -0.0114(7) -0.0045(7) -0.0146(7) C34 0.0588(11) 0.0749(13) 0.0666(12) -0.0131(10) -0.0186(9) -0.0174(10) C35 0.0796(15) 0.0907(17) 0.0641(13) -0.0318(12) -0.0107(11) -0.0236(13) C36 0.0913(16) 0.0617(12) 0.0741(14) -0.0356(11) -0.0030(12) -0.0116(11) C37 0.0737(13) 0.0457(9) 0.0603(11) -0.0156(8) -0.0042(9) -0.0069(9) N41 0.0712(10) 0.0547(9) 0.0527(8) -0.0127(7) -0.0046(7) -0.0170(8) N42 0.0716(11) 0.0684(11) 0.0609(10) -0.0256(8) -0.0148(8) -0.0020(9) C42 0.0564(10) 0.0557(10) 0.0443(8) -0.0106(7) 0.0013(7) -0.0175(8) N43 0.0724(10) 0.0580(9) 0.0487(8) -0.0113(7) -0.0073(7) -0.0173(8) C44 0.0887(16) 0.0700(13) 0.0569(11) -0.0062(10) -0.0202(11) -0.0179(12) C45 0.0890(16) 0.0608(12) 0.0706(14) -0.0002(10) -0.0219(12) -0.0097(11) C46 0.0866(15) 0.0522(11) 0.0670(13) -0.0097(9) -0.0077(11) -0.0147(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 1.9887(9) . ? Cu1 O1 1.9888(9) 2_656 ? Cu1 N11 2.0104(11) . ? Cu1 N11 2.0104(11) 2_656 ? O1 C1 1.2610(15) . ? O2 C1 1.2632(15) . ? C1 C2 1.4838(16) . ? C2 C7 1.3951(17) . ? C2 C3 1.4032(17) . ? O3 C3 1.3515(15) . ? O3 H3 0.9023 . ? C3 C4 1.3874(18) . ? C4 C5 1.373(2) . ? C4 H4 0.9300 . ? C5 C6 1.383(2) . ? C5 H5 0.9300 . ? C6 C7 1.3804(19) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? N11 C16 1.3350(19) . ? N11 C12 1.3544(15) . ? N12 C12 1.3199(18) . ? N12 H12A 0.8825 . ? N12 H12B 0.8124 . ? C12 N13 1.3480(16) . ? N13 C14 1.315(2) . ? C14 C15 1.380(2) . ? C14 H14 0.9300 . ? C15 C16 1.366(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? O21 C21 1.226(2) . ? O22 C21 1.292(2) . ? O22 H22 0.8753 . ? C21 C22 1.472(2) . ? C22 C27 1.384(3) . ? C22 C23 1.396(3) . ? O23 C23 1.350(2) . ? O23 H23 0.9655 . ? C23 C24 1.388(3) . ? C24 C25 1.369(3) . ? C24 H26 0.9300 . ? C25 C26 1.372(3) . ? C25 H25 0.9300 . ? C26 C27 1.372(3) . ? C26 H56 0.9300 . ? C27 H27 0.9300 . ? O31 C31 1.237(2) . ? O32 C31 1.296(2) . ? O32 H32 0.8870 . ? C31 C32 1.472(2) . ? C32 C37 1.393(2) . ? C32 C33 1.395(3) . ? O33 C33 1.351(2) . ? O33 H33 0.9007 . ? C33 C34 1.388(3) . ? C34 C35 1.364(3) . ? C34 H34 0.9300 . ? C35 C36 1.374(3) . ? C35 H35 0.9300 . ? C36 C37 1.373(3) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? N41 C46 1.328(3) . ? N41 C42 1.349(2) . ? N42 C42 1.322(3) . ? N42 H42A 0.8703 . ? N42 H42B 0.8816 . ? C42 N43 1.347(2) . ? N43 C44 1.327(3) . ? C44 C45 1.368(3) . ? C44 H44 0.9300 . ? C45 C46 1.364(3) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? 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 O1 Cu1 O1 180.0 . 2_656 ? O1 Cu1 N11 87.14(4) . . ? O1 Cu1 N11 92.86(4) 2_656 . ? O1 Cu1 N11 92.86(4) . 2_656 ? O1 Cu1 N11 87.14(4) 2_656 2_656 ? N11 Cu1 N11 180.00(3) . 2_656 ? C1 O1 Cu1 101.75(8) . . ? O1 C1 O2 121.43(11) . . ? O1 C1 C2 119.45(11) . . ? O2 C1 C2 119.08(11) . . ? C7 C2 C3 118.73(11) . . ? C7 C2 C1 121.22(11) . . ? C3 C2 C1 120.03(11) . . ? C3 O3 H3 102.7 . . ? O3 C3 C4 117.92(12) . . ? O3 C3 C2 121.87(11) . . ? C4 C3 C2 120.21(12) . . ? C5 C4 C3 119.86(13) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.82(13) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 119.79(14) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C2 120.59(13) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? C16 N11 C12 116.99(11) . . ? C16 N11 Cu1 117.58(9) . . ? C12 N11 Cu1 124.36(9) . . ? C12 N12 H12A 118.9 . . ? C12 N12 H12B 120.4 . . ? H12A N12 H12B 120.7 . . ? N12 C12 N13 117.06(11) . . ? N12 C12 N11 119.32(11) . . ? N13 C12 N11 123.62(12) . . ? C14 N13 C12 117.15(12) . . ? N13 C14 C15 123.16(15) . . ? N13 C14 H14 118.4 . . ? C15 C14 H14 118.4 . . ? C16 C15 C14 116.32(15) . . ? C16 C15 H15 121.8 . . ? C14 C15 H15 121.8 . . ? N11 C16 C15 122.56(13) . . ? N11 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? C21 O22 H22 111.6 . . ? O21 C21 O22 121.93(17) . . ? O21 C21 C22 121.91(17) . . ? O22 C21 C22 116.16(15) . . ? C27 C22 C23 118.41(18) . . ? C27 C22 C21 121.66(17) . . ? C23 C22 C21 119.93(16) . . ? C23 O23 H23 104.3 . . ? O23 C23 C24 117.81(19) . . ? O23 C23 C22 121.97(19) . . ? C24 C23 C22 120.21(19) . . ? C25 C24 C23 119.8(2) . . ? C25 C24 H26 120.1 . . ? C23 C24 H26 120.1 . . ? C24 C25 C26 120.6(2) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C27 119.9(2) . . ? C25 C26 H56 120.0 . . ? C27 C26 H56 120.0 . . ? C26 C27 C22 121.1(2) . . ? C26 C27 H27 119.5 . . ? C22 C27 H27 119.5 . . ? C31 O32 H32 112.0 . . ? O31 C31 O32 122.62(17) . . ? O31 C31 C32 121.64(17) . . ? O32 C31 C32 115.74(15) . . ? C37 C32 C33 118.75(17) . . ? C37 C32 C31 120.93(17) . . ? C33 C32 C31 120.32(15) . . ? C33 O33 H33 101.2 . . ? O33 C33 C34 117.88(17) . . ? O33 C33 C32 122.22(16) . . ? C34 C33 C32 119.89(17) . . ? C35 C34 C33 120.0(2) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C36 121.0(2) . . ? C34 C35 H35 119.5 . . ? C36 C35 H35 119.5 . . ? C37 C36 C35 119.7(2) . . ? C37 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C36 C37 C32 120.7(2) . . ? C36 C37 H37 119.7 . . ? C32 C37 H37 119.7 . . ? C46 N41 C42 117.34(17) . . ? C42 N42 H42A 119.1 . . ? C42 N42 H42B 119.7 . . ? H42A N42 H42B 119.6 . . ? N42 C42 N43 118.47(17) . . ? N42 C42 N41 118.15(17) . . ? N43 C42 N41 123.38(18) . . ? C44 N43 C42 116.89(18) . . ? N43 C44 C45 123.3(2) . . ? N43 C44 H44 118.4 . . ? C45 C44 H44 118.4 . . ? C46 C45 C44 116.2(2) . . ? C46 C45 H45 121.9 . . ? C44 C45 H45 121.9 . . ? N41 C46 C45 122.9(2) . . ? N41 C46 H46 118.6 . . ? C45 C46 H46 118.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O2 0.90 1.68 2.5269(14) 155.9 . N12 H12A N13 0.88 2.13 3.0161(16) 178.6 2_666 N12 H12B O3 0.81 2.28 3.0062(17) 148.8 1_655 O22 H22 N43 0.88 1.79 2.658(2) 174.5 1_645 O23 H23 O21 0.97 1.70 2.584(2) 151.1 . O32 H32 N41 0.89 1.76 2.638(2) 171.0 2_565 O33 H33 O31 0.90 1.73 2.586(2) 156.9 . N42 H42A O21 0.87 2.10 2.950(2) 166.1 1_465 N42 H42A O21 0.87 2.10 2.950(2) 166.1 1_465 N42 H42B O31 0.88 2.15 3.012(2) 166.4 2_565 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.772 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.045