# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_cusml5r2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 Cl Cu N3 O3' _chemical_formula_weight 473.40 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.516(2) _cell_length_b 13.668(3) _cell_length_c 17.620(2) _cell_angle_alpha 75.658(4) _cell_angle_beta 84.462(7) _cell_angle_gamma 70.26(2) _cell_volume 2089.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4.91 _cell_measurement_theta_max 11.90 _exptl_crystal_description Rectangular _exptl_crystal_colour 'Dark brown' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 1.202 _exptl_absorpt_correction_type 'psi scans' _exptl_absorpt_correction_T_min 0.8699 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8742 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7303 _reflns_number_gt 4756 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0400P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7303 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 0.49360(5) 0.60551(3) 0.35736(3) 0.04042(14) Uani 1 1 d . . . Cl1 Cl 0.58044(12) 0.74293(7) 0.32311(6) 0.0537(3) Uani 1 1 d . . . O1 O 0.3366(3) 0.66995(17) 0.42231(14) 0.0446(7) Uani 1 1 d . . . O2 O -0.0483(3) 0.7074(2) 0.61183(17) 0.0689(9) Uani 1 1 d . . . H2A H -0.0444 0.7682 0.5974 0.103 Uiso 1 1 calc R . . O3 O 0.6392(3) 0.52790(18) 0.28868(14) 0.0460(7) Uani 1 1 d . . . N1 N 0.4584(3) 0.4696(2) 0.38946(16) 0.0352(7) Uani 1 1 d . . . N2 N 0.5524(3) 0.3948(2) 0.35101(17) 0.0423(8) Uani 1 1 d . . . H2B H 0.5493 0.3310 0.3585 0.051 Uiso 1 1 calc R . . N3 N 0.7567(4) 0.3642(2) 0.26513(18) 0.0451(8) Uani 1 1 d . . . C1 C 0.2632(4) 0.5150(3) 0.4838(2) 0.0366(9) Uani 1 1 d . . . C2 C 0.2508(4) 0.6242(3) 0.4717(2) 0.0398(9) Uani 1 1 d . . . C3 C 0.1429(4) 0.6862(3) 0.5156(2) 0.0463(10) Uani 1 1 d . . . H3A H 0.1307 0.7584 0.5077 0.056 Uiso 1 1 calc R . . C4 C 0.0539(4) 0.6426(3) 0.5706(2) 0.0454(10) Uani 1 1 d . . . C5 C 0.0686(5) 0.5356(3) 0.5848(2) 0.0480(10) Uani 1 1 d . . . H5A H 0.0109 0.5060 0.6232 0.058 Uiso 1 1 calc R . . C6 C 0.1708(4) 0.4745(3) 0.5407(2) 0.0461(10) Uani 1 1 d . . . H6A H 0.1794 0.4028 0.5488 0.055 Uiso 1 1 calc R . . C7 C 0.3621(4) 0.4437(3) 0.4403(2) 0.0407(9) Uani 1 1 d . . . H7A H 0.3570 0.3751 0.4490 0.049 Uiso 1 1 calc R . . C8 C 0.6493(4) 0.4313(3) 0.3007(2) 0.0393(9) Uani 1 1 d . . . C9 C 0.7958(5) 0.2479(3) 0.2898(2) 0.0515(11) Uani 1 1 d . . . H9A H 0.7523 0.2303 0.3414 0.062 Uiso 1 1 calc R . . H9B H 0.9034 0.2174 0.2948 0.062 Uiso 1 1 calc R . . C10 C 0.7467(5) 0.1947(3) 0.2362(2) 0.0471(10) Uani 1 1 d . . . C11 C 0.6419(6) 0.2482(4) 0.1801(3) 0.0672(13) Uani 1 1 d . . . H11A H 0.5957 0.3215 0.1735 0.081 Uiso 1 1 calc R . . C12 C 0.6031(6) 0.1941(4) 0.1325(3) 0.0799(15) Uani 1 1 d . . . H12A H 0.5320 0.2314 0.0939 0.096 Uiso 1 1 calc R . . C13 C 0.6694(7) 0.0863(5) 0.1423(3) 0.0828(16) Uani 1 1 d . . . H13A H 0.6447 0.0504 0.1099 0.099 Uiso 1 1 calc R . . C14 C 0.7710(6) 0.0320(4) 0.1994(3) 0.0813(16) Uani 1 1 d . . . H14A H 0.8144 -0.0417 0.2069 0.098 Uiso 1 1 calc R . . C15 C 0.8109(5) 0.0854(3) 0.2471(3) 0.0611(12) Uani 1 1 d . . . H15A H 0.8807 0.0476 0.2862 0.073 Uiso 1 1 calc R . . C16 C 0.8599(5) 0.4071(3) 0.2104(2) 0.0556(11) Uani 1 1 d . . . H16A H 0.9582 0.3534 0.2151 0.067 Uiso 1 1 calc R . . H16B H 0.8678 0.4686 0.2256 0.067 Uiso 1 1 calc R . . C17 C 0.8146(6) 0.4401(3) 0.1259(3) 0.0608(12) Uani 1 1 d . . . C18 C 0.9096(8) 0.3973(4) 0.0712(3) 0.0996(19) Uani 1 1 d . . . H18A H 1.0013 0.3461 0.0868 0.120 Uiso 1 1 calc R . . C19 C 0.8727(11) 0.4284(6) -0.0075(4) 0.136(3) Uani 1 1 d . . . H19A H 0.9376 0.3976 -0.0445 0.163 Uiso 1 1 calc R . . C20 C 0.7406(12) 0.5045(6) -0.0291(4) 0.139(3) Uani 1 1 d . . . H20A H 0.7177 0.5300 -0.0820 0.167 Uiso 1 1 calc R . . C21 C 0.6396(10) 0.5447(6) 0.0253(4) 0.135(3) Uani 1 1 d . . . H21A H 0.5455 0.5925 0.0101 0.161 Uiso 1 1 calc R . . C22 C 0.6791(7) 0.5136(4) 0.1024(3) 0.0944(18) Uani 1 1 d . . . H22A H 0.6126 0.5430 0.1394 0.113 Uiso 1 1 calc R . . Cu2 Cu 0.37222(5) 1.19070(3) 0.29898(3) 0.04006(14) Uani 1 1 d . . . Cl2 Cl 0.25735(11) 1.36615(7) 0.26245(6) 0.0496(3) Uani 1 1 d . . . O4 O 0.4767(3) 1.20564(17) 0.37932(14) 0.0440(6) Uani 1 1 d . . . O5 O 0.7753(3) 1.10748(19) 0.60256(14) 0.0551(8) Uani 1 1 d . . . H5B H 0.7445 1.1725 0.5971 0.083 Uiso 1 1 calc R . . O6 O 0.2588(3) 1.15428(18) 0.22716(15) 0.0501(7) Uani 1 1 d . . . N4 N 0.4737(3) 1.0395(2) 0.31773(17) 0.0396(7) Uani 1 1 d . . . N5 N 0.4279(4) 0.9918(2) 0.26860(17) 0.0447(8) Uani 1 1 d . . . H5C H 0.4697 0.9258 0.2672 0.054 Uiso 1 1 calc R . . N6 N 0.2585(4) 1.0195(2) 0.17276(19) 0.0495(8) Uani 1 1 d . . . C23 C 0.6273(4) 1.0194(3) 0.4244(2) 0.0373(9) Uani 1 1 d . . . C24 C 0.5725(4) 1.1283(3) 0.4293(2) 0.0375(9) Uani 1 1 d . . . C25 C 0.6230(4) 1.1556(3) 0.4903(2) 0.0399(9) Uani 1 1 d . . . H25A H 0.5856 1.2258 0.4956 0.048 Uiso 1 1 calc R . . C26 C 0.7265(5) 1.0816(3) 0.5426(2) 0.0441(10) Uani 1 1 d . . . C27 C 0.7858(5) 0.9745(3) 0.5368(2) 0.0482(10) Uani 1 1 d . . . H27A H 0.8577 0.9246 0.5714 0.058 Uiso 1 1 calc R . . C28 C 0.7339(5) 0.9464(3) 0.4785(2) 0.0474(10) Uani 1 1 d . . . H28A H 0.7710 0.8756 0.4745 0.057 Uiso 1 1 calc R . . C29 C 0.5749(4) 0.9808(3) 0.3688(2) 0.0425(10) Uani 1 1 d . . . H29A H 0.6160 0.9085 0.3692 0.051 Uiso 1 1 calc R . . C30 C 0.3120(4) 1.0579(3) 0.2230(2) 0.0437(10) Uani 1 1 d . . . C31 C 0.3346(5) 0.9143(3) 0.1549(3) 0.0597(12) Uani 1 1 d . . . H31A H 0.4372 0.8894 0.1720 0.072 Uiso 1 1 calc R . . H31B H 0.3367 0.9227 0.0985 0.072 Uiso 1 1 calc R . . C32 C 0.2637(5) 0.8297(3) 0.1924(3) 0.0580(12) Uani 1 1 d . . . C33 C 0.3165(6) 0.7334(4) 0.1689(4) 0.0938(18) Uani 1 1 d . . . H33A H 0.3891 0.7242 0.1296 0.113 Uiso 1 1 calc R . . C34 C 0.2609(8) 0.6515(4) 0.2040(4) 0.105(2) Uani 1 1 d . . . H34A H 0.2985 0.5867 0.1890 0.127 Uiso 1 1 calc R . . C35 C 0.1524(8) 0.6642(5) 0.2599(4) 0.101(2) Uani 1 1 d . . . H35A H 0.1150 0.6087 0.2825 0.121 Uiso 1 1 calc R . . C36 C 0.0976(7) 0.7591(5) 0.2832(3) 0.0893(17) Uani 1 1 d . . . H36A H 0.0231 0.7683 0.3216 0.107 Uiso 1 1 calc R . . C37 C 0.1544(6) 0.8409(3) 0.2489(3) 0.0656(13) Uani 1 1 d . . . H37A H 0.1173 0.9051 0.2648 0.079 Uiso 1 1 calc R . . C38 C 0.1252(5) 1.0867(3) 0.1276(2) 0.0527(11) Uani 1 1 d . . . H38A H 0.0734 1.1461 0.1516 0.063 Uiso 1 1 calc R . . H38B H 0.0589 1.0454 0.1302 0.063 Uiso 1 1 calc R . . C39 C 0.1567(5) 1.1302(3) 0.0428(2) 0.0512(11) Uani 1 1 d . . . C40 C 0.2704(6) 1.1693(5) 0.0206(3) 0.0901(17) Uani 1 1 d . . . H40A H 0.3353 1.1668 0.0578 0.108 Uiso 1 1 calc R . . C41 C 0.2908(8) 1.2135(5) -0.0583(4) 0.112(2) Uani 1 1 d . . . H41A H 0.3690 1.2408 -0.0734 0.135 Uiso 1 1 calc R . . C42 C 0.1963(9) 1.2169(5) -0.1135(3) 0.101(2) Uani 1 1 d . . . H42A H 0.2106 1.2454 -0.1662 0.122 Uiso 1 1 calc R . . C43 C 0.0829(8) 1.1786(5) -0.0905(3) 0.0964(19) Uani 1 1 d . . . H43A H 0.0172 1.1820 -0.1276 0.116 Uiso 1 1 calc R . . C44 C 0.0621(6) 1.1348(4) -0.0139(3) 0.0747(14) Uani 1 1 d . . . H44A H -0.0164 1.1077 0.0006 0.090 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 0.0521(3) 0.0265(2) 0.0453(3) -0.0123(2) 0.0007(2) -0.0136(2) Cl1 0.0641(7) 0.0294(5) 0.0710(7) -0.0127(5) -0.0001(6) -0.0187(5) O1 0.0605(18) 0.0270(13) 0.0472(15) -0.0136(11) 0.0075(14) -0.0142(13) O2 0.073(2) 0.0434(16) 0.082(2) -0.0222(15) 0.0251(18) -0.0097(16) O3 0.0593(18) 0.0307(14) 0.0531(16) -0.0151(12) 0.0042(14) -0.0188(13) N1 0.0447(19) 0.0210(14) 0.0393(17) -0.0107(13) -0.0030(16) -0.0065(14) N2 0.051(2) 0.0258(15) 0.0510(19) -0.0140(14) 0.0034(17) -0.0107(15) N3 0.047(2) 0.0336(17) 0.054(2) -0.0147(15) 0.0031(17) -0.0092(16) C1 0.041(2) 0.0315(19) 0.038(2) -0.0070(16) -0.0034(18) -0.0124(18) C2 0.051(2) 0.034(2) 0.035(2) -0.0075(17) -0.0053(19) -0.0128(19) C3 0.057(3) 0.0304(19) 0.049(2) -0.0109(18) 0.004(2) -0.011(2) C4 0.043(2) 0.041(2) 0.049(2) -0.0115(19) -0.003(2) -0.007(2) C5 0.052(3) 0.044(2) 0.046(2) -0.0048(19) 0.001(2) -0.018(2) C6 0.057(3) 0.031(2) 0.050(2) -0.0067(18) -0.007(2) -0.015(2) C7 0.049(2) 0.0262(19) 0.046(2) -0.0072(17) -0.005(2) -0.0113(18) C8 0.044(2) 0.036(2) 0.040(2) -0.0131(18) -0.0044(19) -0.0106(19) C9 0.051(3) 0.034(2) 0.063(3) -0.0136(19) 0.001(2) -0.0033(19) C10 0.047(3) 0.042(2) 0.052(3) -0.016(2) 0.013(2) -0.013(2) C11 0.076(3) 0.056(3) 0.077(3) -0.017(3) 0.001(3) -0.030(3) C12 0.086(4) 0.087(4) 0.081(4) -0.025(3) -0.010(3) -0.041(3) C13 0.094(4) 0.099(5) 0.087(4) -0.048(4) 0.021(4) -0.059(4) C14 0.082(4) 0.064(3) 0.113(5) -0.049(3) 0.033(4) -0.031(3) C15 0.061(3) 0.043(2) 0.077(3) -0.021(2) 0.013(3) -0.013(2) C16 0.048(3) 0.051(2) 0.066(3) -0.018(2) 0.012(2) -0.014(2) C17 0.082(4) 0.044(2) 0.057(3) -0.016(2) 0.018(3) -0.023(3) C18 0.127(5) 0.078(4) 0.086(4) -0.029(3) 0.038(4) -0.027(4) C19 0.219(10) 0.111(6) 0.081(5) -0.043(4) 0.056(6) -0.059(6) C20 0.256(12) 0.111(6) 0.065(4) -0.018(4) 0.002(6) -0.081(7) C21 0.177(8) 0.114(5) 0.086(5) -0.010(4) -0.026(5) -0.016(5) C22 0.111(5) 0.083(4) 0.065(4) -0.012(3) -0.006(3) -0.003(4) Cu2 0.0483(3) 0.0265(2) 0.0458(3) -0.0109(2) -0.0006(2) -0.0109(2) Cl2 0.0553(6) 0.0293(5) 0.0602(6) -0.0093(4) -0.0031(5) -0.0088(5) O4 0.0583(17) 0.0242(12) 0.0481(15) -0.0086(11) -0.0100(14) -0.0087(13) O5 0.084(2) 0.0352(14) 0.0446(16) -0.0085(12) -0.0165(15) -0.0138(15) O6 0.0605(18) 0.0321(14) 0.0591(17) -0.0158(12) -0.0072(14) -0.0112(13) N4 0.051(2) 0.0306(16) 0.0417(18) -0.0146(14) -0.0018(16) -0.0148(16) N5 0.059(2) 0.0290(16) 0.050(2) -0.0148(15) -0.0067(18) -0.0137(16) N6 0.056(2) 0.0419(18) 0.055(2) -0.0209(16) -0.0090(18) -0.0131(17) C23 0.048(2) 0.0263(18) 0.040(2) -0.0114(17) 0.0003(19) -0.0124(18) C24 0.043(2) 0.0293(19) 0.038(2) -0.0061(17) 0.0074(19) -0.0126(18) C25 0.056(3) 0.0239(18) 0.039(2) -0.0081(16) -0.001(2) -0.0105(18) C26 0.064(3) 0.035(2) 0.036(2) -0.0092(17) 0.003(2) -0.020(2) C27 0.061(3) 0.033(2) 0.043(2) -0.0069(18) -0.004(2) -0.007(2) C28 0.061(3) 0.0253(19) 0.054(2) -0.0138(18) 0.000(2) -0.0079(19) C29 0.052(3) 0.0232(18) 0.051(2) -0.0092(17) 0.001(2) -0.0098(18) C30 0.047(3) 0.039(2) 0.048(2) -0.0134(19) 0.004(2) -0.017(2) C31 0.068(3) 0.049(2) 0.065(3) -0.028(2) -0.013(2) -0.009(2) C32 0.058(3) 0.038(2) 0.083(3) -0.018(2) -0.027(3) -0.012(2) C33 0.078(4) 0.064(3) 0.154(6) -0.054(4) -0.001(4) -0.022(3) C34 0.102(5) 0.055(3) 0.174(7) -0.040(4) -0.021(5) -0.030(4) C35 0.116(6) 0.062(4) 0.125(6) 0.012(4) -0.044(5) -0.041(4) C36 0.113(5) 0.088(4) 0.067(3) 0.010(3) -0.026(3) -0.046(4) C37 0.091(4) 0.049(3) 0.057(3) -0.002(2) -0.025(3) -0.023(3) C38 0.050(3) 0.050(2) 0.065(3) -0.018(2) -0.007(2) -0.020(2) C39 0.052(3) 0.047(2) 0.056(3) -0.021(2) -0.003(2) -0.012(2) C40 0.082(4) 0.135(5) 0.069(4) -0.017(3) 0.001(3) -0.060(4) C41 0.106(5) 0.139(6) 0.093(5) -0.017(4) 0.031(4) -0.058(5) C42 0.123(6) 0.103(5) 0.053(4) -0.022(3) 0.018(4) -0.007(4) C43 0.119(6) 0.100(5) 0.059(4) -0.027(3) -0.014(4) -0.011(4) C44 0.084(4) 0.073(3) 0.075(4) -0.027(3) -0.016(3) -0.023(3) _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 1.897(2) . ? Cu1 N1 1.935(3) . ? Cu1 O3 1.957(2) . ? Cu1 Cl1 2.2284(11) . ? O1 C2 1.324(4) . ? O2 C4 1.364(4) . ? O3 C8 1.256(4) . ? N1 C7 1.293(4) . ? N1 N2 1.383(4) . ? N2 C8 1.349(5) . ? N3 C8 1.344(4) . ? N3 C9 1.464(4) . ? N3 C16 1.472(5) . ? C1 C6 1.403(5) . ? C1 C2 1.419(5) . ? C1 C7 1.426(5) . ? C2 C3 1.399(5) . ? C3 C4 1.380(5) . ? C4 C5 1.381(5) . ? C5 C6 1.370(5) . ? C9 C10 1.515(5) . ? C10 C11 1.358(6) . ? C10 C15 1.380(5) . ? C11 C12 1.392(6) . ? C12 C13 1.366(7) . ? C13 C14 1.353(7) . ? C14 C15 1.392(6) . ? C16 C17 1.504(6) . ? C17 C18 1.357(6) . ? C17 C22 1.367(7) . ? C18 C19 1.389(9) . ? C19 C20 1.349(10) . ? C20 C21 1.368(10) . ? C21 C22 1.369(8) . ? Cu2 O4 1.894(2) . ? Cu2 N4 1.920(3) . ? Cu2 O6 1.988(3) . ? Cu2 Cl2 2.2272(11) . ? O4 C24 1.330(4) . ? O5 C26 1.359(4) . ? O6 C30 1.260(4) . ? N4 C29 1.292(4) . ? N4 N5 1.382(4) . ? N5 C30 1.348(5) . ? N6 C30 1.348(5) . ? N6 C38 1.460(5) . ? N6 C31 1.472(4) . ? C23 C28 1.401(5) . ? C23 C29 1.420(5) . ? C23 C24 1.422(4) . ? C24 C25 1.393(5) . ? C25 C26 1.372(5) . ? C26 C27 1.406(5) . ? C27 C28 1.367(5) . ? C31 C32 1.514(6) . ? C32 C37 1.366(6) . ? C32 C33 1.394(6) . ? C33 C34 1.381(8) . ? C34 C35 1.354(8) . ? C35 C36 1.374(7) . ? C36 C37 1.385(7) . ? C38 C39 1.506(5) . ? C39 C40 1.347(6) . ? C39 C44 1.384(6) . ? C40 C41 1.394(7) . ? C41 C42 1.370(8) . ? C42 C43 1.340(8) . ? C43 C44 1.359(7) . ? 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 N1 92.70(11) . . ? O1 Cu1 O3 172.40(11) . . ? N1 Cu1 O3 80.95(11) . . ? O1 Cu1 Cl1 95.34(8) . . ? N1 Cu1 Cl1 168.93(9) . . ? O3 Cu1 Cl1 91.52(8) . . ? C2 O1 Cu1 127.7(2) . . ? C8 O3 Cu1 113.6(2) . . ? C7 N1 N2 119.7(3) . . ? C7 N1 Cu1 128.1(2) . . ? N2 N1 Cu1 112.2(2) . . ? C8 N2 N1 113.8(3) . . ? C8 N3 C9 123.0(3) . . ? C8 N3 C16 118.4(3) . . ? C9 N3 C16 117.4(3) . . ? C6 C1 C2 118.6(3) . . ? C6 C1 C7 117.4(3) . . ? C2 C1 C7 123.9(3) . . ? O1 C2 C3 118.5(3) . . ? O1 C2 C1 123.9(3) . . ? C3 C2 C1 117.6(3) . . ? C4 C3 C2 121.5(3) . . ? O2 C4 C3 118.5(3) . . ? O2 C4 C5 120.2(4) . . ? C3 C4 C5 121.3(4) . . ? C6 C5 C4 117.9(4) . . ? C5 C6 C1 122.9(3) . . ? N1 C7 C1 123.4(3) . . ? O3 C8 N3 120.7(4) . . ? O3 C8 N2 119.2(3) . . ? N3 C8 N2 120.1(3) . . ? N3 C9 C10 116.0(3) . . ? C11 C10 C15 119.2(4) . . ? C11 C10 C9 123.6(4) . . ? C15 C10 C9 117.2(4) . . ? C10 C11 C12 120.4(4) . . ? C13 C12 C11 120.2(5) . . ? C14 C13 C12 119.7(5) . . ? C13 C14 C15 120.5(5) . . ? C10 C15 C14 119.9(5) . . ? N3 C16 C17 114.4(4) . . ? C18 C17 C22 118.6(5) . . ? C18 C17 C16 120.0(5) . . ? C22 C17 C16 121.3(4) . . ? C17 C18 C19 121.4(6) . . ? C20 C19 C18 118.4(7) . . ? C19 C20 C21 121.3(7) . . ? C20 C21 C22 119.1(7) . . ? C17 C22 C21 121.0(6) . . ? O4 Cu2 N4 92.60(11) . . ? O4 Cu2 O6 170.67(10) . . ? N4 Cu2 O6 80.77(12) . . ? O4 Cu2 Cl2 92.46(7) . . ? N4 Cu2 Cl2 173.34(9) . . ? O6 Cu2 Cl2 94.68(8) . . ? C24 O4 Cu2 127.4(2) . . ? C30 O6 Cu2 112.7(2) . . ? C29 N4 N5 118.8(3) . . ? C29 N4 Cu2 128.4(2) . . ? N5 N4 Cu2 112.8(2) . . ? C30 N5 N4 114.1(3) . . ? C30 N6 C38 120.0(3) . . ? C30 N6 C31 123.4(3) . . ? C38 N6 C31 116.3(3) . . ? C28 C23 C29 118.5(3) . . ? C28 C23 C24 118.7(3) . . ? C29 C23 C24 122.8(3) . . ? O4 C24 C25 118.0(3) . . ? O4 C24 C23 124.2(3) . . ? C25 C24 C23 117.9(3) . . ? C26 C25 C24 121.8(3) . . ? O5 C26 C25 122.1(3) . . ? O5 C26 C27 116.9(3) . . ? C25 C26 C27 121.0(4) . . ? C28 C27 C26 117.6(4) . . ? C27 C28 C23 123.0(3) . . ? N4 C29 C23 124.2(3) . . ? O6 C30 N6 121.8(4) . . ? O6 C30 N5 119.2(3) . . ? N6 C30 N5 118.9(3) . . ? N6 C31 C32 114.7(4) . . ? C37 C32 C33 118.2(5) . . ? C37 C32 C31 124.2(4) . . ? C33 C32 C31 117.6(5) . . ? C34 C33 C32 120.0(6) . . ? C35 C34 C33 120.9(6) . . ? C34 C35 C36 119.9(6) . . ? C35 C36 C37 119.3(6) . . ? C32 C37 C36 121.6(5) . . ? N6 C38 C39 114.0(3) . . ? C40 C39 C44 118.7(5) . . ? C40 C39 C38 122.1(4) . . ? C44 C39 C38 119.2(4) . . ? C39 C40 C41 120.0(5) . . ? C42 C41 C40 120.4(6) . . ? C43 C42 C41 119.0(6) . . ? C42 C43 C44 121.2(6) . . ? C43 C44 C39 120.7(6) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.353 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 955520' ####################################################################### # # 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_cupy _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H25 Cu N5 O6' _chemical_formula_weight 579.06 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 P2(1)/n 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 9.587(1) _cell_length_b 16.270(2) _cell_length_c 17.130(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.44(1) _cell_angle_gamma 90.00 _cell_volume 2618.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4.76 _cell_measurement_theta_max 12.46 _exptl_crystal_description Rectangular _exptl_crystal_colour 'Dark brown' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1196 _exptl_absorpt_coefficient_mu 0.886 _exptl_absorpt_correction_type 'psi scans' _exptl_absorpt_correction_T_min 0.9042 _exptl_absorpt_correction_T_max 0.9847 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5931 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4618 _reflns_number_gt 3433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0300P)^2^+0.9000P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4618 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.86358(4) 0.45736(2) 0.095769(18) 0.04645(12) Uani 1 1 d . . . O1 O 0.9325(2) 0.37655(13) 0.03581(10) 0.0641(6) Uani 1 1 d . . . O2 O 1.0380(2) 0.22944(13) -0.17698(12) 0.0666(6) Uani 1 1 d . . . H2A H 1.0048 0.2181 -0.2236 0.100 Uiso 1 1 calc R . . O3 O 0.78951(19) 0.55012(11) 0.14756(10) 0.0449(4) Uani 1 1 d . . . N1 N 0.7505(2) 0.50819(13) 0.00245(12) 0.0413(5) Uani 1 1 d . . . N2 N 0.6675(2) 0.57124(13) 0.02224(12) 0.0460(6) Uani 1 1 d . . . H2B H 0.6068 0.5977 -0.0124 0.055 Uiso 1 1 calc R . . N3 N 0.6101(2) 0.64259(13) 0.12948(12) 0.0445(5) Uani 1 1 d . . . N4 N 0.9866(2) 0.41806(13) 0.19546(12) 0.0449(5) Uani 1 1 d . . . C1 C 0.8261(3) 0.42449(16) -0.09614(14) 0.0415(6) Uani 1 1 d . . . C2 C 0.9132(3) 0.37019(17) -0.04252(15) 0.0462(7) Uani 1 1 d . . . C3 C 0.9802(3) 0.30565(18) -0.07353(16) 0.0506(7) Uani 1 1 d . . . H3A H 1.0354 0.2690 -0.0388 0.061 Uiso 1 1 calc R . . C4 C 0.9671(3) 0.29455(18) -0.15452(16) 0.0497(7) Uani 1 1 d . . . C5 C 0.8833(3) 0.34702(18) -0.20744(16) 0.0515(7) Uani 1 1 d . . . H5A H 0.8737 0.3395 -0.2621 0.062 Uiso 1 1 calc R . . C6 C 0.8147(3) 0.41018(18) -0.17839(15) 0.0491(7) Uani 1 1 d . . . H6A H 0.7581 0.4452 -0.2143 0.059 Uiso 1 1 calc R . . C7 C 0.7464(3) 0.49037(16) -0.07138(15) 0.0441(6) Uani 1 1 d . . . H7A H 0.6889 0.5219 -0.1103 0.053 Uiso 1 1 calc R . . C8 C 0.6905(3) 0.58762(15) 0.10145(15) 0.0409(6) Uani 1 1 d . . . C9 C 0.4860(3) 0.68159(16) 0.07992(15) 0.0464(7) Uani 1 1 d . . . H9A H 0.4201 0.6970 0.1137 0.056 Uiso 1 1 calc R . . H9B H 0.4386 0.6415 0.0418 0.056 Uiso 1 1 calc R . . C10 C 0.5180(3) 0.75653(16) 0.03511(15) 0.0464(7) Uani 1 1 d . . . C11 C 0.4104(4) 0.7909(2) -0.02103(18) 0.0687(9) Uani 1 1 d . . . H11A H 0.3201 0.7676 -0.0308 0.082 Uiso 1 1 calc R . . C12 C 0.4373(6) 0.8600(3) -0.0627(2) 0.1011(14) Uani 1 1 d . . . H12A H 0.3648 0.8830 -0.1006 0.121 Uiso 1 1 calc R . . C13 C 0.5688(6) 0.8941(3) -0.0486(3) 0.1063(15) Uani 1 1 d . . . H13A H 0.5862 0.9401 -0.0775 0.128 Uiso 1 1 calc R . . C14 C 0.6758(5) 0.8619(2) 0.0073(3) 0.0914(12) Uani 1 1 d . . . H14A H 0.7651 0.8865 0.0175 0.110 Uiso 1 1 calc R . . C15 C 0.6506(4) 0.79247(19) 0.04879(19) 0.0625(8) Uani 1 1 d . . . H15A H 0.7240 0.7698 0.0863 0.075 Uiso 1 1 calc R . . C16 C 0.6527(3) 0.66973(16) 0.21299(15) 0.0495(7) Uani 1 1 d . . . H16A H 0.6302 0.7276 0.2159 0.059 Uiso 1 1 calc R . . H16B H 0.7551 0.6640 0.2292 0.059 Uiso 1 1 calc R . . C17 C 0.5830(3) 0.62348(17) 0.27085(15) 0.0447(6) Uani 1 1 d . . . C18 C 0.5418(4) 0.6656(2) 0.33204(19) 0.0769(10) Uani 1 1 d . . . H18A H 0.5536 0.7223 0.3357 0.092 Uiso 1 1 calc R . . C19 C 0.4830(6) 0.6244(3) 0.3880(2) 0.1148(16) Uani 1 1 d . . . H19A H 0.4535 0.6535 0.4285 0.138 Uiso 1 1 calc R . . C20 C 0.4681(5) 0.5408(3) 0.3841(2) 0.0962(13) Uani 1 1 d . . . H20A H 0.4287 0.5131 0.4220 0.115 Uiso 1 1 calc R . . C21 C 0.5106(4) 0.4987(2) 0.3253(2) 0.0718(9) Uani 1 1 d . . . H21A H 0.5014 0.4418 0.3228 0.086 Uiso 1 1 calc R . . C22 C 0.5673(3) 0.53950(18) 0.26928(17) 0.0556(7) Uani 1 1 d . . . H22A H 0.5961 0.5097 0.2290 0.067 Uiso 1 1 calc R . . C23 C 1.1056(3) 0.37685(18) 0.19354(18) 0.0555(7) Uani 1 1 d . . . H23A H 1.1275 0.3649 0.1443 0.067 Uiso 1 1 calc R . . C24 C 1.1975(4) 0.3512(2) 0.2610(2) 0.0715(9) Uani 1 1 d . . . H24A H 1.2805 0.3230 0.2574 0.086 Uiso 1 1 calc R . . C25 C 1.1650(4) 0.3677(2) 0.3333(2) 0.0710(10) Uani 1 1 d . . . H25A H 1.2253 0.3508 0.3799 0.085 Uiso 1 1 calc R . . C26 C 1.0431(4) 0.40922(19) 0.33632(17) 0.0652(9) Uani 1 1 d . . . H26A H 1.0189 0.4206 0.3851 0.078 Uiso 1 1 calc R . . C27 C 0.9561(3) 0.43424(18) 0.26688(16) 0.0548(7) Uani 1 1 d . . . H27A H 0.8736 0.4633 0.2695 0.066 Uiso 1 1 calc R . . O4 O 0.6750(3) 0.32647(19) 0.19507(15) 0.1129(10) Uani 1 1 d . . . O5 O 0.4531(3) 0.33472(17) 0.15600(16) 0.0925(8) Uani 1 1 d . . . O6 O 0.5890(3) 0.40314(13) 0.09717(11) 0.0678(6) Uani 1 1 d . . . N5 N 0.5729(3) 0.35450(15) 0.14945(14) 0.0530(6) Uani 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 0.0565(2) 0.0451(2) 0.03841(18) 0.00136(15) 0.01087(14) 0.01121(17) O1 0.0880(15) 0.0648(13) 0.0401(11) 0.0001(9) 0.0143(10) 0.0319(12) O2 0.0671(13) 0.0724(15) 0.0607(12) -0.0261(11) 0.0134(10) 0.0088(12) O3 0.0529(11) 0.0421(10) 0.0395(9) -0.0006(8) 0.0088(8) 0.0062(9) N1 0.0504(13) 0.0354(12) 0.0403(12) 0.0033(10) 0.0143(10) 0.0045(11) N2 0.0592(15) 0.0412(13) 0.0380(12) 0.0040(10) 0.0101(10) 0.0144(11) N3 0.0589(14) 0.0344(12) 0.0413(12) 0.0002(10) 0.0123(11) 0.0066(11) N4 0.0519(14) 0.0424(13) 0.0411(12) 0.0032(10) 0.0111(10) 0.0017(11) C1 0.0433(15) 0.0431(15) 0.0398(14) -0.0005(12) 0.0124(12) -0.0033(13) C2 0.0498(16) 0.0483(16) 0.0432(15) -0.0051(13) 0.0156(13) -0.0022(14) C3 0.0542(18) 0.0509(17) 0.0479(16) -0.0046(13) 0.0131(13) 0.0070(15) C4 0.0467(16) 0.0502(17) 0.0545(17) -0.0170(14) 0.0159(14) -0.0088(14) C5 0.0567(18) 0.0603(19) 0.0393(15) -0.0136(14) 0.0142(13) -0.0121(16) C6 0.0526(17) 0.0525(17) 0.0416(15) -0.0002(13) 0.0079(13) -0.0039(14) C7 0.0520(17) 0.0426(15) 0.0400(14) 0.0064(12) 0.0143(13) -0.0013(13) C8 0.0501(16) 0.0311(14) 0.0429(14) 0.0005(12) 0.0130(13) -0.0034(13) C9 0.0509(17) 0.0433(16) 0.0472(15) -0.0041(13) 0.0148(13) 0.0028(13) C10 0.0593(18) 0.0382(15) 0.0435(15) -0.0024(12) 0.0147(13) 0.0084(14) C11 0.084(2) 0.059(2) 0.0554(18) -0.0033(16) -0.0056(17) 0.0117(18) C12 0.147(4) 0.077(3) 0.067(2) 0.023(2) -0.009(3) 0.025(3) C13 0.161(5) 0.065(3) 0.097(3) 0.037(2) 0.034(3) 0.006(3) C14 0.103(3) 0.068(2) 0.113(3) 0.023(2) 0.043(3) -0.009(2) C15 0.068(2) 0.0512(19) 0.073(2) 0.0136(16) 0.0245(17) 0.0076(17) C16 0.0632(18) 0.0374(15) 0.0485(16) -0.0094(12) 0.0123(14) 0.0023(14) C17 0.0443(15) 0.0485(17) 0.0389(14) -0.0038(12) 0.0026(12) 0.0062(13) C18 0.108(3) 0.062(2) 0.069(2) -0.0162(18) 0.039(2) 0.000(2) C19 0.176(5) 0.112(4) 0.078(3) -0.027(3) 0.077(3) -0.016(3) C20 0.128(4) 0.106(3) 0.065(2) 0.006(2) 0.046(2) -0.019(3) C21 0.083(2) 0.065(2) 0.069(2) 0.0098(18) 0.0195(19) -0.0058(19) C22 0.067(2) 0.0502(18) 0.0529(17) -0.0035(14) 0.0200(15) 0.0013(16) C23 0.0560(19) 0.0547(18) 0.0577(18) 0.0106(15) 0.0157(15) 0.0064(16) C24 0.059(2) 0.071(2) 0.081(2) 0.0238(19) 0.0083(18) 0.0107(18) C25 0.072(2) 0.070(2) 0.063(2) 0.0235(18) -0.0067(18) -0.006(2) C26 0.093(3) 0.058(2) 0.0429(16) 0.0052(14) 0.0090(17) -0.009(2) C27 0.0648(19) 0.0512(18) 0.0487(17) 0.0022(14) 0.0118(15) 0.0040(15) O4 0.116(2) 0.124(2) 0.0811(17) 0.0137(17) -0.0231(17) 0.043(2) O5 0.0844(18) 0.095(2) 0.111(2) -0.0024(16) 0.0495(16) -0.0223(16) O6 0.1039(17) 0.0568(13) 0.0463(11) 0.0098(10) 0.0236(11) -0.0148(12) N5 0.0667(18) 0.0480(15) 0.0452(14) -0.0016(12) 0.0132(13) 0.0038(14) _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 1.8678(19) . ? Cu1 N1 1.930(2) . ? Cu1 O3 1.9541(17) . ? Cu1 N4 1.979(2) . ? O1 C2 1.322(3) . ? O2 C4 1.355(3) . ? O3 C8 1.265(3) . ? N1 C7 1.290(3) . ? N1 N2 1.381(3) . ? N2 C8 1.357(3) . ? N3 C8 1.331(3) . ? N3 C9 1.462(3) . ? N3 C16 1.475(3) . ? N4 C23 1.329(3) . ? N4 C27 1.339(3) . ? C1 C6 1.411(3) . ? C1 C2 1.420(4) . ? C1 C7 1.429(4) . ? C2 C3 1.391(4) . ? C3 C4 1.380(4) . ? C4 C5 1.381(4) . ? C5 C6 1.366(4) . ? C9 C10 1.504(4) . ? C10 C15 1.377(4) . ? C10 C11 1.381(4) . ? C11 C12 1.383(5) . ? C12 C13 1.355(6) . ? C13 C14 1.362(6) . ? C14 C15 1.381(4) . ? C16 C17 1.503(4) . ? C17 C22 1.374(4) . ? C17 C18 1.375(4) . ? C18 C19 1.378(5) . ? C19 C20 1.368(6) . ? C20 C21 1.348(5) . ? C21 C22 1.364(4) . ? C23 C24 1.372(4) . ? C24 C25 1.364(5) . ? C25 C26 1.359(5) . ? C26 C27 1.372(4) . ? O4 N5 1.213(3) . ? O5 N5 1.219(3) . ? O6 N5 1.227(3) . ? 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 N1 92.75(8) . . ? O1 Cu1 O3 173.32(8) . . ? N1 Cu1 O3 81.38(8) . . ? O1 Cu1 N4 91.82(9) . . ? N1 Cu1 N4 173.46(9) . . ? O3 Cu1 N4 93.78(8) . . ? C2 O1 Cu1 128.30(18) . . ? C8 O3 Cu1 112.61(15) . . ? C7 N1 N2 120.0(2) . . ? C7 N1 Cu1 128.19(19) . . ? N2 N1 Cu1 111.79(14) . . ? C8 N2 N1 113.8(2) . . ? C8 N3 C9 123.0(2) . . ? C8 N3 C16 118.8(2) . . ? C9 N3 C16 118.0(2) . . ? C23 N4 C27 117.8(2) . . ? C23 N4 Cu1 120.62(18) . . ? C27 N4 Cu1 121.6(2) . . ? C6 C1 C2 117.5(2) . . ? C6 C1 C7 118.7(2) . . ? C2 C1 C7 123.7(2) . . ? O1 C2 C3 117.7(3) . . ? O1 C2 C1 123.6(2) . . ? C3 C2 C1 118.7(2) . . ? C4 C3 C2 121.7(3) . . ? O2 C4 C3 115.9(3) . . ? O2 C4 C5 123.8(2) . . ? C3 C4 C5 120.3(3) . . ? C6 C5 C4 119.0(2) . . ? C5 C6 C1 122.7(3) . . ? N1 C7 C1 123.0(2) . . ? O3 C8 N3 121.0(2) . . ? O3 C8 N2 118.9(2) . . ? N3 C8 N2 120.1(2) . . ? N3 C9 C10 115.0(2) . . ? C15 C10 C11 118.9(3) . . ? C15 C10 C9 122.1(3) . . ? C11 C10 C9 118.9(3) . . ? C10 C11 C12 119.9(4) . . ? C13 C12 C11 120.2(4) . . ? C12 C13 C14 120.8(4) . . ? C13 C14 C15 119.5(4) . . ? C10 C15 C14 120.6(3) . . ? N3 C16 C17 114.6(2) . . ? C22 C17 C18 117.6(3) . . ? C22 C17 C16 123.1(2) . . ? C18 C17 C16 119.1(3) . . ? C17 C18 C19 120.4(3) . . ? C20 C19 C18 120.2(4) . . ? C21 C20 C19 119.9(4) . . ? C20 C21 C22 120.0(3) . . ? C21 C22 C17 121.8(3) . . ? N4 C23 C24 123.0(3) . . ? C25 C24 C23 118.7(3) . . ? C26 C25 C24 119.1(3) . . ? C25 C26 C27 119.6(3) . . ? N4 C27 C26 121.9(3) . . ? O4 N5 O5 119.7(3) . . ? O4 N5 O6 120.7(3) . . ? O5 N5 O6 119.6(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.250 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.044 #=====END _database_code_depnum_ccdc_archive 'CCDC 955521'