# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name A.Ghosh _publ_contact_author_email ghosh_59@yahoo.com _publ_author_name A.Ghosh data_1A _database_code_depnum_ccdc_archive 'CCDC 879879' #TrackingRef '- 1A and 1B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N10 O4 Zn' _chemical_formula_weight 837.19 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' Zn Zn 0.2839 1.4301 '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 9.8880(3) _cell_length_b 11.9657(3) _cell_length_c 14.0680(4) _cell_angle_alpha 86.7020(10) _cell_angle_beta 77.5400(10) _cell_angle_gamma 89.6040(10) _cell_volume 1622.56(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 19256 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 26.7 _exptl_crystal_description Rhombic _exptl_crystal_colour Brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.714 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 2.090 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.5757 _exptl_absorpt_correction_T_max 0.6365 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19256 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 26.71 _reflns_number_total 6766 _reflns_number_gt 5338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WINGX V1.80.03' _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^)+(0.0719P)^2^+0.8586P] 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 6766 _refine_ls_number_parameters 476 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Zn1 Zn 0.63517(4) 0.24423(3) 0.70605(3) 0.03620(13) Uani 1 1 d . . . Cu1 Cu 0.36338(4) 0.21717(4) 0.87774(3) 0.03782(13) Uani 1 1 d . . . Cu2 Cu 0.45024(4) 0.36312(4) 0.57042(3) 0.03887(14) Uani 1 1 d . . . N5 N 0.7210(3) 0.0970(3) 0.6659(3) 0.0512(8) Uani 1 1 d . . . N9 N 0.8373(3) 0.4012(3) 0.7579(3) 0.0523(8) Uani 1 1 d . . . O2 O 0.4115(2) 0.1743(2) 0.74642(18) 0.0448(6) Uani 1 1 d . . . C15 C 0.2910(5) 0.0557(4) 0.5490(3) 0.0543(10) Uani 1 1 d . . . H15 H 0.3280 0.0191 0.4927 0.065 Uiso 1 1 calc R . . O3 O 0.4982(2) 0.3957(2) 0.6927(2) 0.0468(6) Uani 1 1 d . . . O4 O 0.6282(2) 0.2943(2) 0.55759(18) 0.0417(6) Uani 1 1 d . . . C28 C 0.5333(4) 0.2764(4) 0.3793(3) 0.0490(10) Uani 1 1 d . . . O1 O 0.5615(2) 0.2103(2) 0.86218(18) 0.0424(6) Uani 1 1 d . . . C30 C 0.7630(5) 0.2050(4) 0.3110(3) 0.0536(10) Uani 1 1 d . . . H30 H 0.7320 0.1914 0.2549 0.064 Uiso 1 1 calc R . . C4 C 0.7635(5) 0.0430(4) 1.0578(4) 0.0607(12) Uani 1 1 d . . . H4 H 0.8097 0.0055 1.1009 0.073 Uiso 1 1 calc R . . N10 N 0.8731(5) 0.4739(5) 0.7962(5) 0.108(2) Uani 1 1 d . . . N4 N 0.4364(3) 0.3246(3) 0.4381(3) 0.0469(8) Uani 1 1 d . . . N1 N 0.3382(3) 0.2255(3) 1.0194(2) 0.0501(8) Uani 1 1 d . . . N2 N 0.1720(3) 0.2508(3) 0.8707(2) 0.0431(7) Uani 1 1 d . . . C17 C 0.3256(3) 0.1432(3) 0.6922(3) 0.0370(7) Uani 1 1 d . . . C19 C 0.4979(4) 0.4913(4) 0.8351(3) 0.0521(10) Uani 1 1 d . . . H19 H 0.5852 0.4633 0.8375 0.063 Uiso 1 1 calc R . . C6 C 0.5589(4) 0.1365(3) 1.0246(3) 0.0413(8) Uani 1 1 d . . . C13 C 0.0969(4) 0.1284(4) 0.6555(3) 0.0529(10) Uani 1 1 d . . . H13 H 0.0022 0.1422 0.6716 0.064 Uiso 1 1 calc R . . N6 N 0.6998(4) 0.0039(3) 0.6901(2) 0.0536(9) Uani 1 1 d . . . C12 C 0.1820(3) 0.1635(3) 0.7167(3) 0.0395(8) Uani 1 1 d . . . C26 C 0.2203(5) 0.4324(5) 0.4431(4) 0.0763(15) Uani 1 1 d . . . H26A H 0.2749 0.5007 0.4288 0.092 Uiso 1 1 calc R . . H26B H 0.1446 0.4407 0.4095 0.092 Uiso 1 1 calc R . . C23 C 0.3023(4) 0.5053(3) 0.7592(3) 0.0473(9) Uani 1 1 d . . . C18 C 0.4343(4) 0.4621(3) 0.7602(3) 0.0415(8) Uani 1 1 d . . . N3 N 0.2672(3) 0.4324(3) 0.6080(3) 0.0502(8) Uani 1 1 d . . . C2 C 0.7609(4) 0.1167(4) 0.8963(3) 0.0488(9) Uani 1 1 d . . . H2 H 0.8067 0.1280 0.8314 0.059 Uiso 1 1 calc R . . C33 C 0.8538(4) 0.2415(3) 0.4790(3) 0.0438(8) Uani 1 1 d . . . H33 H 0.8865 0.2530 0.5349 0.053 Uiso 1 1 calc R . . C5 C 0.6304(5) 0.0802(3) 1.0893(3) 0.0526(10) Uani 1 1 d . . . H5 H 0.5869 0.0680 1.1546 0.063 Uiso 1 1 calc R . . C32 C 0.9432(4) 0.2047(4) 0.3968(3) 0.0519(10) Uani 1 1 d . . . H32 H 1.0360 0.1936 0.3979 0.062 Uiso 1 1 calc R . . C11 C 0.1179(4) 0.2220(3) 0.8011(3) 0.0454(9) Uani 1 1 d . . . C29 C 0.6691(4) 0.2469(3) 0.3918(3) 0.0417(8) Uani 1 1 d . . . C22 C 0.2375(5) 0.5731(4) 0.8340(4) 0.0630(12) Uani 1 1 d . . . H22 H 0.1487 0.5995 0.8344 0.076 Uiso 1 1 calc R . . C24 C 0.2267(4) 0.4846(4) 0.6847(4) 0.0560(11) Uani 1 1 d . . . C1 C 0.6249(3) 0.1562(3) 0.9256(3) 0.0370(8) Uani 1 1 d . . . N8 N 0.8090(3) 0.3279(3) 0.7153(3) 0.0496(8) Uani 1 1 d . . . C34 C 0.7149(3) 0.2614(3) 0.4778(3) 0.0366(7) Uani 1 1 d . . . C31 C 0.8977(5) 0.1844(4) 0.3139(3) 0.0576(11) Uani 1 1 d . . . H31 H 0.9581 0.1568 0.2603 0.069 Uiso 1 1 calc R . . C16 C 0.3778(4) 0.0899(3) 0.6063(3) 0.0487(9) Uani 1 1 d . . . H16 H 0.4725 0.0773 0.5876 0.058 Uiso 1 1 calc R . . C3 C 0.8274(4) 0.0625(4) 0.9606(3) 0.0571(11) Uani 1 1 d . . . H3 H 0.9176 0.0379 0.9387 0.069 Uiso 1 1 calc R . . C7 C 0.4247(5) 0.1817(4) 1.0654(3) 0.0510(10) Uani 1 1 d . . . C21 C 0.3011(5) 0.6012(4) 0.9056(4) 0.0680(13) Uani 1 1 d . . . H21 H 0.2566 0.6467 0.9540 0.082 Uiso 1 1 calc R . . C10 C 0.0804(5) 0.3118(4) 0.9483(3) 0.0629(12) Uani 1 1 d . . . H10A H 0.1046 0.3908 0.9404 0.075 Uiso 1 1 calc R . . H10B H -0.0150 0.3044 0.9424 0.075 Uiso 1 1 calc R . . C14 C 0.1505(5) 0.0746(4) 0.5732(3) 0.0562(11) Uani 1 1 d . . . H14 H 0.0931 0.0509 0.5338 0.067 Uiso 1 1 calc R . . C20 C 0.4321(5) 0.5617(4) 0.9058(3) 0.0601(11) Uani 1 1 d . . . H20 H 0.4771 0.5823 0.9538 0.072 Uiso 1 1 calc R . . C8 C 0.2136(5) 0.2748(5) 1.0804(4) 0.0780(15) Uani 1 1 d . . . H8A H 0.1971 0.2375 1.1450 0.094 Uiso 1 1 calc R . . H8B H 0.2324 0.3531 1.0873 0.094 Uiso 1 1 calc R . . C27 C 0.3079(5) 0.3400(5) 0.4010(4) 0.0715(14) Uani 1 1 d . . . H27A H 0.3327 0.3537 0.3308 0.086 Uiso 1 1 calc R . . H27B H 0.2544 0.2711 0.4147 0.086 Uiso 1 1 calc R . . C25 C 0.1614(5) 0.4236(5) 0.5472(4) 0.0776(16) Uani 1 1 d . . . H25A H 0.1134 0.3524 0.5637 0.093 Uiso 1 1 calc R . . H25B H 0.0937 0.4825 0.5630 0.093 Uiso 1 1 calc R . . C9 C 0.0940(7) 0.2678(9) 1.0448(5) 0.155(4) Uani 1 1 d . . . H9A H 0.0217 0.3029 1.0913 0.186 Uiso 1 1 calc R . . H9B H 0.0704 0.1889 1.0486 0.186 Uiso 1 1 calc R . . N7 N 0.6774(8) -0.0902(4) 0.7081(4) 0.121(2) Uani 1 1 d . . . H28 H 0.519(4) 0.256(3) 0.325(3) 0.041(10) Uiso 1 1 d . . . H7 H 0.401(4) 0.176(3) 1.136(3) 0.048(11) Uiso 1 1 d . . . H11 H 0.027(5) 0.241(3) 0.801(3) 0.055(12) Uiso 1 1 d . . . H24 H 0.140(5) 0.508(4) 0.696(4) 0.068(14) 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 Zn1 0.0298(2) 0.0471(2) 0.0318(2) -0.00264(17) -0.00700(16) 0.00735(16) Cu1 0.0305(2) 0.0492(3) 0.0317(2) -0.00562(19) -0.00144(17) 0.00465(17) Cu2 0.0310(2) 0.0444(3) 0.0438(3) -0.00116(19) -0.01431(18) 0.00542(17) N5 0.0525(19) 0.0454(19) 0.051(2) -0.0014(16) -0.0011(16) 0.0086(15) N9 0.0347(16) 0.065(2) 0.061(2) -0.0166(19) -0.0177(15) 0.0111(15) O2 0.0305(12) 0.0723(18) 0.0329(14) -0.0133(12) -0.0069(10) 0.0054(11) C15 0.071(3) 0.056(2) 0.042(2) -0.0082(19) -0.023(2) 0.008(2) O3 0.0367(13) 0.0602(16) 0.0473(16) -0.0136(13) -0.0152(11) 0.0164(11) O4 0.0367(12) 0.0535(15) 0.0373(14) -0.0061(11) -0.0130(11) 0.0144(11) C28 0.058(2) 0.055(2) 0.041(2) -0.0037(19) -0.024(2) -0.0020(19) O1 0.0327(12) 0.0630(16) 0.0319(13) -0.0012(12) -0.0081(10) 0.0031(11) C30 0.069(3) 0.056(2) 0.035(2) -0.0002(18) -0.0113(19) 0.007(2) C4 0.072(3) 0.054(2) 0.066(3) 0.009(2) -0.039(2) 0.001(2) N10 0.069(3) 0.122(4) 0.147(5) -0.085(4) -0.036(3) 0.009(3) N4 0.0421(17) 0.0552(19) 0.049(2) -0.0017(16) -0.0234(15) 0.0022(14) N1 0.0468(18) 0.064(2) 0.0370(18) -0.0130(16) 0.0003(15) 0.0057(15) N2 0.0345(15) 0.0485(18) 0.0419(18) -0.0030(14) 0.0014(13) 0.0122(13) C17 0.0379(17) 0.0408(18) 0.0328(19) 0.0037(15) -0.0104(14) 0.0050(14) C19 0.050(2) 0.056(2) 0.051(3) -0.0096(19) -0.0108(19) 0.0093(18) C6 0.051(2) 0.0421(19) 0.0325(19) -0.0014(15) -0.0141(16) 0.0000(16) C13 0.040(2) 0.059(2) 0.063(3) 0.008(2) -0.0206(19) -0.0009(17) N6 0.072(2) 0.058(2) 0.0277(17) -0.0057(16) -0.0047(15) -0.0001(18) C12 0.0356(17) 0.0408(19) 0.043(2) 0.0056(15) -0.0115(15) 0.0014(14) C26 0.058(3) 0.088(4) 0.094(4) 0.014(3) -0.045(3) 0.002(3) C23 0.0398(19) 0.044(2) 0.054(2) -0.0010(18) -0.0027(17) 0.0074(15) C18 0.0381(18) 0.0397(19) 0.043(2) -0.0020(16) -0.0017(16) 0.0031(14) N3 0.0337(15) 0.059(2) 0.061(2) -0.0038(17) -0.0176(15) 0.0071(14) C2 0.0396(19) 0.064(2) 0.044(2) -0.0012(19) -0.0118(17) 0.0029(17) C33 0.0400(18) 0.053(2) 0.038(2) -0.0024(17) -0.0082(16) 0.0063(16) C5 0.070(3) 0.050(2) 0.041(2) 0.0016(18) -0.019(2) -0.0015(19) C32 0.041(2) 0.059(2) 0.050(2) 0.0059(19) 0.0013(18) 0.0077(17) C11 0.0278(16) 0.053(2) 0.053(2) 0.0028(18) -0.0063(16) 0.0087(15) C29 0.047(2) 0.0417(19) 0.036(2) 0.0022(15) -0.0095(16) 0.0001(15) C22 0.054(2) 0.061(3) 0.067(3) -0.007(2) 0.001(2) 0.022(2) C24 0.0330(19) 0.061(3) 0.072(3) -0.005(2) -0.008(2) 0.0123(18) C1 0.0392(17) 0.0405(18) 0.0351(19) -0.0031(15) -0.0162(15) -0.0024(14) N8 0.0378(16) 0.059(2) 0.054(2) -0.0115(17) -0.0112(15) 0.0032(14) C34 0.0393(17) 0.0366(17) 0.0342(19) -0.0025(14) -0.0085(15) 0.0036(14) C31 0.061(3) 0.066(3) 0.039(2) 0.002(2) 0.0034(19) 0.012(2) C16 0.045(2) 0.060(2) 0.044(2) -0.0090(19) -0.0140(17) 0.0066(17) C3 0.049(2) 0.062(3) 0.063(3) 0.002(2) -0.019(2) 0.0066(19) C7 0.061(2) 0.063(3) 0.028(2) -0.0095(18) -0.0063(18) -0.002(2) C21 0.076(3) 0.062(3) 0.060(3) -0.015(2) 0.000(3) 0.022(2) C10 0.053(2) 0.069(3) 0.059(3) -0.014(2) 0.007(2) 0.024(2) C14 0.064(3) 0.056(2) 0.057(3) 0.003(2) -0.034(2) -0.008(2) C20 0.073(3) 0.055(3) 0.052(3) -0.013(2) -0.011(2) 0.009(2) C8 0.067(3) 0.106(4) 0.054(3) -0.021(3) 0.007(2) 0.026(3) C27 0.051(2) 0.101(4) 0.074(3) -0.019(3) -0.036(2) 0.014(2) C25 0.042(2) 0.117(4) 0.083(4) -0.007(3) -0.033(2) 0.014(2) C9 0.107(5) 0.290(12) 0.069(4) -0.073(6) -0.011(4) 0.124(7) N7 0.223(7) 0.062(3) 0.061(3) -0.002(2) 0.005(4) -0.018(4) _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 Zn1 N5 2.007(3) . ? Zn1 N8 2.027(3) . ? Zn1 O4 2.155(3) . ? Zn1 O1 2.175(2) . ? Zn1 O3 2.278(3) . ? Zn1 O2 2.311(2) . ? Cu1 O2 1.905(2) . ? Cu1 O1 1.926(2) . ? Cu1 N2 1.954(3) . ? Cu1 N1 1.963(3) . ? Cu2 O4 1.914(2) . ? Cu2 O3 1.941(3) . ? Cu2 N3 1.965(3) . ? Cu2 N4 1.976(3) . ? N5 N6 1.153(5) . ? N9 N10 1.146(5) . ? N9 N8 1.159(5) . ? O2 C17 1.326(4) . ? C15 C14 1.377(6) . ? C15 C16 1.377(6) . ? O3 C18 1.325(4) . ? O4 C34 1.335(4) . ? C28 N4 1.281(5) . ? C28 C29 1.431(5) . ? O1 C1 1.333(4) . ? C30 C31 1.361(6) . ? C30 C29 1.417(6) . ? C4 C5 1.374(6) . ? C4 C3 1.384(7) . ? N4 C27 1.481(5) . ? N1 C7 1.273(6) . ? N1 C8 1.481(5) . ? N2 C11 1.277(5) . ? N2 C10 1.484(5) . ? C17 C16 1.395(5) . ? C17 C12 1.410(5) . ? C19 C20 1.390(6) . ? C19 C18 1.399(6) . ? C6 C5 1.408(6) . ? C6 C1 1.413(5) . ? C6 C7 1.442(6) . ? C13 C14 1.361(6) . ? C13 C12 1.409(5) . ? N6 N7 1.152(6) . ? C12 C11 1.437(6) . ? C26 C25 1.453(8) . ? C26 C27 1.470(7) . ? C23 C18 1.403(5) . ? C23 C22 1.406(6) . ? C23 C24 1.446(6) . ? N3 C24 1.265(6) . ? N3 C25 1.495(5) . ? C2 C3 1.361(6) . ? C2 C1 1.406(5) . ? C33 C32 1.387(6) . ? C33 C34 1.396(5) . ? C32 C31 1.373(6) . ? C29 C34 1.400(5) . ? C22 C21 1.355(7) . ? C21 C20 1.377(7) . ? C10 C9 1.460(9) . ? C8 C9 1.385(9) . ? 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 N5 Zn1 N8 98.83(14) . . ? N5 Zn1 O4 91.50(12) . . ? N8 Zn1 O4 98.90(12) . . ? N5 Zn1 O1 101.30(12) . . ? N8 Zn1 O1 96.05(12) . . ? O4 Zn1 O1 158.57(9) . . ? N5 Zn1 O3 154.21(13) . . ? N8 Zn1 O3 97.85(12) . . ? O4 Zn1 O3 66.52(9) . . ? O1 Zn1 O3 96.34(10) . . ? N5 Zn1 O2 94.44(12) . . ? N8 Zn1 O2 160.46(12) . . ? O4 Zn1 O2 95.01(9) . . ? O1 Zn1 O2 67.16(9) . . ? O3 Zn1 O2 75.20(10) . . ? O2 Cu1 O1 80.85(10) . . ? O2 Cu1 N2 93.27(12) . . ? O1 Cu1 N2 167.20(12) . . ? O2 Cu1 N1 165.28(14) . . ? O1 Cu1 N1 91.33(12) . . ? N2 Cu1 N1 96.74(14) . . ? O4 Cu2 O3 78.29(10) . . ? O4 Cu2 N3 169.99(13) . . ? O3 Cu2 N3 92.27(13) . . ? O4 Cu2 N4 92.10(12) . . ? O3 Cu2 N4 169.94(12) . . ? N3 Cu2 N4 97.49(14) . . ? N6 N5 Zn1 136.5(3) . . ? N10 N9 N8 175.8(5) . . ? C17 O2 Cu1 127.0(2) . . ? C17 O2 Zn1 132.0(2) . . ? Cu1 O2 Zn1 98.57(10) . . ? C14 C15 C16 121.4(4) . . ? C18 O3 Cu2 128.7(2) . . ? C18 O3 Zn1 130.0(2) . . ? Cu2 O3 Zn1 97.86(11) . . ? C34 O4 Cu2 129.4(2) . . ? C34 O4 Zn1 126.0(2) . . ? Cu2 O4 Zn1 103.01(11) . . ? N4 C28 C29 128.7(4) . . ? C1 O1 Cu1 123.8(2) . . ? C1 O1 Zn1 128.9(2) . . ? Cu1 O1 Zn1 102.71(11) . . ? C31 C30 C29 121.4(4) . . ? C5 C4 C3 118.8(4) . . ? C28 N4 C27 113.6(4) . . ? C28 N4 Cu2 123.5(3) . . ? C27 N4 Cu2 122.8(3) . . ? C7 N1 C8 115.7(4) . . ? C7 N1 Cu1 121.4(3) . . ? C8 N1 Cu1 122.7(3) . . ? C11 N2 C10 116.1(3) . . ? C11 N2 Cu1 123.1(3) . . ? C10 N2 Cu1 120.7(3) . . ? O2 C17 C16 119.6(3) . . ? O2 C17 C12 122.6(3) . . ? C16 C17 C12 117.8(3) . . ? C20 C19 C18 120.7(4) . . ? C5 C6 C1 119.7(4) . . ? C5 C6 C7 117.5(4) . . ? C1 C6 C7 122.5(3) . . ? C14 C13 C12 121.3(4) . . ? N7 N6 N5 175.5(5) . . ? C13 C12 C17 119.5(4) . . ? C13 C12 C11 117.9(3) . . ? C17 C12 C11 122.6(3) . . ? C25 C26 C27 117.7(5) . . ? C18 C23 C22 119.4(4) . . ? C18 C23 C24 123.8(4) . . ? C22 C23 C24 116.8(4) . . ? O3 C18 C19 120.3(3) . . ? O3 C18 C23 121.6(4) . . ? C19 C18 C23 118.1(4) . . ? C24 N3 C25 114.3(4) . . ? C24 N3 Cu2 124.5(3) . . ? C25 N3 Cu2 121.1(3) . . ? C3 C2 C1 121.7(4) . . ? C32 C33 C34 120.0(4) . . ? C4 C5 C6 121.2(4) . . ? C31 C32 C33 121.5(4) . . ? N2 C11 C12 128.1(3) . . ? C34 C29 C30 118.8(3) . . ? C34 C29 C28 123.4(4) . . ? C30 C29 C28 117.7(4) . . ? C21 C22 C23 121.7(4) . . ? N3 C24 C23 127.9(4) . . ? O1 C1 C2 121.1(3) . . ? O1 C1 C6 121.6(3) . . ? C2 C1 C6 117.3(3) . . ? N9 N8 Zn1 137.1(3) . . ? O4 C34 C33 120.0(3) . . ? O4 C34 C29 121.0(3) . . ? C33 C34 C29 118.9(3) . . ? C30 C31 C32 119.1(4) . . ? C15 C16 C17 120.9(4) . . ? C2 C3 C4 121.4(4) . . ? N1 C7 C6 127.5(4) . . ? C22 C21 C20 119.3(4) . . ? C9 C10 N2 110.8(4) . . ? C13 C14 C15 119.1(4) . . ? C21 C20 C19 120.7(4) . . ? C9 C8 N1 115.0(5) . . ? C26 C27 N4 114.2(4) . . ? C26 C25 N3 113.3(4) . . ? C8 C9 C10 124.4(8) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.71 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.968 _refine_diff_density_min -1.031 _refine_diff_density_rms 0.092 data_1B _database_code_depnum_ccdc_archive 'CCDC 879880' #TrackingRef '- 1A and 1B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N10 O4 Zn' _chemical_formula_weight 837.19 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' Zn Zn 0.2839 1.4301 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.453(5) _cell_length_b 11.123(5) _cell_length_c 15.869(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 102.039(5) _cell_angle_gamma 90.000(5) _cell_volume 1631.9(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23309 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 31.2 _exptl_crystal_description Hexagonal _exptl_crystal_colour Green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 2.078 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.5938 _exptl_absorpt_correction_T_max 0.6813 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23309 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 31.16 _reflns_number_total 5181 _reflns_number_gt 3851 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WINGX V1.80.03' _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^)+(0.0394P)^2^+0.2601P] 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 5181 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0744 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Zn1 Zn 0.0000 0.5000 0.0000 0.03318(8) Uani 1 2 d S . . Cu1 Cu -0.24709(2) 0.660074(18) -0.060670(14) 0.03596(8) Uani 1 1 d . . . O1 O -0.15441(13) 0.53948(11) -0.11950(8) 0.0361(3) Uani 1 1 d . . . O2 O -0.20212(14) 0.54467(12) 0.03171(9) 0.0432(3) Uani 1 1 d . . . N1 N -0.24011(16) 0.78034(13) -0.14841(10) 0.0377(3) Uani 1 1 d . . . N2 N -0.39504(16) 0.73750(13) -0.00784(10) 0.0391(3) Uani 1 1 d . . . N3 N -0.02514(18) 0.31527(15) -0.00583(12) 0.0499(4) Uani 1 1 d . . . N4 N -0.12572(18) 0.25915(15) -0.03981(12) 0.0467(4) Uani 1 1 d . . . C6 C -0.15940(19) 0.64732(17) -0.25066(12) 0.0398(4) Uani 1 1 d . . . C17 C -0.28460(18) 0.50728(15) 0.08351(11) 0.0334(4) Uani 1 1 d . . . C13 C -0.4980(2) 0.52550(18) 0.14518(13) 0.0413(4) Uani 1 1 d . . . H13 H -0.5828 0.5658 0.1488 0.050 Uiso 1 1 calc R . . C16 C -0.2458(2) 0.40575(17) 0.13562(12) 0.0411(4) Uani 1 1 d . . . H16 H -0.1607 0.3650 0.1336 0.049 Uiso 1 1 calc R . . C1 C -0.14096(17) 0.54106(17) -0.20051(11) 0.0353(4) Uani 1 1 d . . . C7 C -0.2022(2) 0.76066(18) -0.22011(13) 0.0407(4) Uani 1 1 d . . . C12 C -0.41222(18) 0.56970(16) 0.08979(11) 0.0341(4) Uani 1 1 d . . . C10 C -0.4505(3) 0.86053(18) -0.03023(15) 0.0542(5) Uani 1 1 d . . . H10A H -0.3992 0.9158 0.0128 0.065 Uiso 1 1 calc R . . H10B H -0.5519 0.8629 -0.0271 0.065 Uiso 1 1 calc R . . C15 C -0.3324(2) 0.36559(19) 0.18988(13) 0.0460(5) Uani 1 1 d . . . H15 H -0.3050 0.2982 0.2241 0.055 Uiso 1 1 calc R . . C14 C -0.4604(2) 0.42505(19) 0.19379(13) 0.0485(5) Uani 1 1 d . . . H14 H -0.5197 0.3964 0.2293 0.058 Uiso 1 1 calc R . . C9 C -0.4366(2) 0.90441(18) -0.11791(14) 0.0518(5) Uani 1 1 d . . . H9A H -0.4740 0.9858 -0.1259 0.062 Uiso 1 1 calc R . . H9B H -0.4957 0.8542 -0.1615 0.062 Uiso 1 1 calc R . . C5 C -0.1358(2) 0.6435(2) -0.33553(14) 0.0553(5) Uani 1 1 d . . . H5 H -0.1437 0.7139 -0.3678 0.066 Uiso 1 1 calc R . . C8 C -0.2818(2) 0.90333(16) -0.13125(15) 0.0489(5) Uani 1 1 d . . . H8A H -0.2741 0.9548 -0.1794 0.059 Uiso 1 1 calc R . . H8B H -0.2171 0.9341 -0.0802 0.059 Uiso 1 1 calc R . . C2 C -0.1080(2) 0.43441(19) -0.23948(14) 0.0465(5) Uani 1 1 d . . . H2 H -0.0975 0.3632 -0.2081 0.056 Uiso 1 1 calc R . . C3 C -0.0910(2) 0.4338(2) -0.32372(15) 0.0587(6) Uani 1 1 d . . . H3 H -0.0720 0.3617 -0.3488 0.070 Uiso 1 1 calc R . . C4 C -0.1016(3) 0.5380(3) -0.37126(15) 0.0664(7) Uani 1 1 d . . . H4 H -0.0857 0.5370 -0.4271 0.080 Uiso 1 1 calc R . . C11 C -0.45488(19) 0.68222(17) 0.04632(13) 0.0391(4) Uani 1 1 d . . . N5 N -0.2234(2) 0.2025(2) -0.07405(19) 0.0916(8) Uani 1 1 d . . . H11 H -0.534(2) 0.7254(18) 0.0647(12) 0.042(5) Uiso 1 1 d . . . H7 H -0.203(2) 0.8245(18) -0.2577(13) 0.043(6) 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 Zn1 0.03002(14) 0.02943(14) 0.04035(17) 0.00321(11) 0.00796(11) 0.00624(10) Cu1 0.04184(13) 0.02931(12) 0.03868(14) 0.00657(8) 0.01284(9) 0.01122(8) O1 0.0424(7) 0.0324(6) 0.0349(7) 0.0045(5) 0.0114(5) 0.0084(5) O2 0.0399(7) 0.0461(7) 0.0483(8) 0.0179(6) 0.0197(6) 0.0166(6) N1 0.0387(8) 0.0294(7) 0.0438(9) 0.0066(6) 0.0057(6) 0.0042(6) N2 0.0411(8) 0.0331(7) 0.0428(9) -0.0003(7) 0.0080(7) 0.0116(6) N3 0.0438(9) 0.0321(8) 0.0684(12) 0.0002(8) -0.0004(8) 0.0028(7) N4 0.0460(9) 0.0380(8) 0.0593(11) -0.0070(8) 0.0182(8) 0.0027(7) C6 0.0341(9) 0.0466(10) 0.0379(10) 0.0062(8) 0.0059(7) 0.0027(7) C17 0.0328(8) 0.0354(9) 0.0315(9) -0.0002(7) 0.0058(7) -0.0002(7) C13 0.0334(9) 0.0505(11) 0.0410(11) -0.0081(8) 0.0102(7) -0.0042(8) C16 0.0392(9) 0.0407(10) 0.0426(11) 0.0067(8) 0.0069(8) 0.0027(7) C1 0.0276(8) 0.0417(9) 0.0360(10) -0.0005(7) 0.0054(7) 0.0011(7) C7 0.0384(9) 0.0402(10) 0.0413(11) 0.0133(8) 0.0033(8) -0.0013(7) C12 0.0340(8) 0.0371(9) 0.0312(9) -0.0062(7) 0.0065(7) -0.0005(7) C10 0.0666(14) 0.0377(10) 0.0602(14) 0.0039(9) 0.0176(11) 0.0234(10) C15 0.0535(11) 0.0437(10) 0.0400(11) 0.0078(8) 0.0077(9) -0.0066(9) C14 0.0522(11) 0.0564(12) 0.0397(11) -0.0024(9) 0.0163(9) -0.0143(9) C9 0.0618(13) 0.0341(10) 0.0585(14) 0.0075(9) 0.0100(10) 0.0193(9) C5 0.0541(12) 0.0720(15) 0.0404(12) 0.0131(10) 0.0110(9) 0.0093(10) C8 0.0615(13) 0.0290(9) 0.0538(12) 0.0070(8) 0.0067(10) 0.0046(8) C2 0.0465(10) 0.0449(11) 0.0487(12) -0.0048(9) 0.0111(9) 0.0067(8) C3 0.0551(13) 0.0730(16) 0.0476(13) -0.0156(12) 0.0101(10) 0.0142(11) C4 0.0640(14) 0.101(2) 0.0362(12) 0.0017(12) 0.0139(10) 0.0195(14) C11 0.0354(9) 0.0403(10) 0.0417(11) -0.0072(8) 0.0082(8) 0.0092(7) N5 0.0525(13) 0.0733(15) 0.147(2) -0.0476(16) 0.0166(14) -0.0120(11) _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 Zn1 N3 2.0683(19) 3_565 ? Zn1 N3 2.0683(19) . ? Zn1 O2 2.1335(15) 3_565 ? Zn1 O2 2.1335(15) . ? Zn1 O1 2.1828(13) . ? Zn1 O1 2.1828(13) 3_565 ? Zn1 Cu1 2.9351(10) 3_565 ? Zn1 Cu1 2.9351(11) . ? Cu1 O2 1.9281(14) . ? Cu1 N1 1.9418(15) . ? Cu1 O1 1.9441(13) . ? Cu1 N2 1.9722(15) . ? O1 C1 1.318(2) . ? O2 C17 1.313(2) . ? N1 C7 1.281(2) . ? N1 C8 1.465(2) . ? N2 C11 1.280(2) . ? N2 C10 1.482(2) . ? N3 N4 1.171(2) . ? N4 N5 1.156(3) . ? C6 C5 1.411(3) . ? C6 C1 1.415(3) . ? C6 C7 1.439(3) . ? C17 C16 1.402(3) . ? C17 C12 1.413(2) . ? C13 C14 1.362(3) . ? C13 C12 1.404(3) . ? C16 C15 1.380(3) . ? C1 C2 1.402(3) . ? C12 C11 1.445(3) . ? C10 C9 1.506(3) . ? C15 C14 1.392(3) . ? C9 C8 1.522(3) . ? C5 C4 1.371(4) . ? C2 C3 1.379(3) . ? C3 C4 1.375(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Zn1 N3 180.0 3_565 . ? N3 Zn1 O2 98.15(6) 3_565 3_565 ? N3 Zn1 O2 81.85(6) . 3_565 ? N3 Zn1 O2 81.85(6) 3_565 . ? N3 Zn1 O2 98.15(6) . . ? O2 Zn1 O2 180.00(9) 3_565 . ? N3 Zn1 O1 83.62(6) 3_565 . ? N3 Zn1 O1 96.38(6) . . ? O2 Zn1 O1 108.14(5) 3_565 . ? O2 Zn1 O1 71.86(5) . . ? N3 Zn1 O1 96.38(6) 3_565 3_565 ? N3 Zn1 O1 83.62(6) . 3_565 ? O2 Zn1 O1 71.86(5) 3_565 3_565 ? O2 Zn1 O1 108.14(5) . 3_565 ? O1 Zn1 O1 180.00(7) . 3_565 ? N3 Zn1 Cu1 120.78(5) 3_565 3_565 ? N3 Zn1 Cu1 59.22(5) . 3_565 ? O2 Zn1 Cu1 41.02(4) 3_565 3_565 ? O2 Zn1 Cu1 138.98(4) . 3_565 ? O1 Zn1 Cu1 138.52(3) . 3_565 ? O1 Zn1 Cu1 41.48(3) 3_565 3_565 ? N3 Zn1 Cu1 59.22(5) 3_565 . ? N3 Zn1 Cu1 120.78(5) . . ? O2 Zn1 Cu1 138.98(4) 3_565 . ? O2 Zn1 Cu1 41.02(4) . . ? O1 Zn1 Cu1 41.48(3) . . ? O1 Zn1 Cu1 138.52(3) 3_565 . ? Cu1 Zn1 Cu1 180.0 3_565 . ? O2 Cu1 N1 165.63(6) . . ? O2 Cu1 O1 81.71(6) . . ? N1 Cu1 O1 92.58(6) . . ? O2 Cu1 N2 91.77(6) . . ? N1 Cu1 N2 97.88(7) . . ? O1 Cu1 N2 159.38(6) . . ? O2 Cu1 Zn1 46.57(4) . . ? N1 Cu1 Zn1 120.62(5) . . ? O1 Cu1 Zn1 48.05(4) . . ? N2 Cu1 Zn1 135.38(5) . . ? C1 O1 Cu1 127.15(11) . . ? C1 O1 Zn1 131.83(10) . . ? Cu1 O1 Zn1 90.48(5) . . ? C17 O2 Cu1 128.41(11) . . ? C17 O2 Zn1 138.75(11) . . ? Cu1 O2 Zn1 92.41(5) . . ? C7 N1 C8 117.43(16) . . ? C7 N1 Cu1 125.22(13) . . ? C8 N1 Cu1 117.35(13) . . ? C11 N2 C10 114.86(16) . . ? C11 N2 Cu1 121.83(12) . . ? C10 N2 Cu1 123.25(13) . . ? N4 N3 Zn1 128.68(14) . . ? N5 N4 N3 178.7(2) . . ? C5 C6 C1 119.09(19) . . ? C5 C6 C7 117.36(18) . . ? C1 C6 C7 123.55(17) . . ? O2 C17 C16 120.51(16) . . ? O2 C17 C12 121.03(15) . . ? C16 C17 C12 118.44(16) . . ? C14 C13 C12 121.68(18) . . ? C15 C16 C17 120.80(18) . . ? O1 C1 C2 119.62(17) . . ? O1 C1 C6 122.27(16) . . ? C2 C1 C6 118.11(17) . . ? N1 C7 C6 126.83(17) . . ? C13 C12 C17 119.04(17) . . ? C13 C12 C11 117.52(16) . . ? C17 C12 C11 123.31(16) . . ? N2 C10 C9 115.20(16) . . ? C16 C15 C14 120.55(19) . . ? C13 C14 C15 119.44(18) . . ? C10 C9 C8 113.45(18) . . ? C4 C5 C6 121.2(2) . . ? N1 C8 C9 109.69(16) . . ? C3 C2 C1 120.9(2) . . ? C4 C3 C2 121.2(2) . . ? C5 C4 C3 119.4(2) . . ? N2 C11 C12 128.16(16) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 31.16 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.353 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.061