# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_shelx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H36 N6 O21 Zn2' _chemical_formula_weight 1091.51 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' 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 P21/c 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 24.516(4) _cell_length_b 7.3474(13) _cell_length_c 23.623(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.650(2) _cell_angle_gamma 90.00 _cell_volume 4195.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 12390 _cell_measurement_theta_min 1.3 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2232 _exptl_absorpt_coefficient_mu 1.242 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7893 _exptl_absorpt_correction_T_max 0.8653 _exptl_absorpt_process_details CRYSALISPRO _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 14.22 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 42141 _diffrn_reflns_av_R_equivalents 0.0621 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.85 _reflns_number_total 9948 _reflns_number_gt 8061 _reflns_threshold_expression >2sigma(I) _computing_data_collection CRYSALISPRO _computing_cell_refinement CRYSALISPRO _computing_data_reduction CRYSALISPRO _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^)+(0.0469P)^2^+1.3037P] 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 9948 _refine_ls_number_parameters 680 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.098 _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 0.210934(14) 0.95913(5) 0.344844(14) 0.01630(10) Uani 1 1 d . . . Zn2 Zn 0.291853(14) 0.72488(5) 0.151924(14) 0.01596(10) Uani 1 1 d . . . O1 O 0.17101(8) 0.9321(3) 0.25783(8) 0.0186(5) Uani 1 1 d . . . O2 O 0.18174(9) 0.9945(3) 0.16715(9) 0.0229(5) Uani 1 1 d . . . O3 O 0.29260(9) 0.9764(3) 0.12304(9) 0.0194(5) Uani 1 1 d . . . O4 O 0.26915(10) 1.2687(3) 0.11677(9) 0.0224(5) Uani 1 1 d . . . O5 O 0.43678(9) 1.3626(4) 0.28633(10) 0.0333(6) Uani 1 1 d . . . O6 O 0.42630(9) 1.3175(4) 0.37535(9) 0.0294(6) Uani 1 1 d . . . H6A H 0.4029 1.2698 0.3930 0.044 Uiso 1 1 calc R . . O7 O 0.35570(9) 1.2008(3) 0.42712(9) 0.0267(5) Uani 1 1 d . . . O8 O 0.27572(8) 1.0539(3) 0.41065(8) 0.0180(5) Uani 1 1 d . . . O9 O 0.21787(9) 0.7073(3) 0.37228(9) 0.0198(5) Uani 1 1 d . . . O10 O 0.21979(10) 0.4067(3) 0.37924(9) 0.0254(5) Uani 1 1 d . . . O11 O 0.06803(10) 0.3029(4) 0.20621(10) 0.0363(6) Uani 1 1 d . . . O12 O 0.08189(10) 0.3414(4) 0.11725(10) 0.0321(6) Uani 1 1 d . . . H12 H 0.1039 0.4008 0.1006 0.048 Uiso 1 1 calc R . . O13 O 0.15079(10) 0.4772(4) 0.06765(9) 0.0328(6) Uani 1 1 d . . . O14 O 0.22795(9) 0.6401(3) 0.08652(9) 0.0203(5) Uani 1 1 d . . . O15 O 0.33122(8) 0.7513(3) 0.23913(8) 0.0172(5) Uani 1 1 d . . . O16 O 0.32460(9) 0.6581(3) 0.32837(9) 0.0257(5) Uani 1 1 d . . . N1 N 0.26542(10) 1.0838(3) 0.30045(10) 0.0135(5) Uani 1 1 d . . . N2 N 0.23818(10) 0.5945(3) 0.19599(10) 0.0153(5) Uani 1 1 d . . . N3 N 0.14182(10) 1.0432(3) 0.37351(10) 0.0161(5) Uani 1 1 d . . . N4 N -0.15830(11) 1.4781(4) 0.53103(12) 0.0231(6) Uani 1 1 d D . . H4 H -0.1909(8) 1.516(4) 0.5416(14) 0.028 Uiso 1 1 d D . . N5 N 0.35749(10) 0.6065(3) 0.12485(10) 0.0170(5) Uani 1 1 d . . . N6 N 0.64903(11) 0.0346(4) -0.01237(12) 0.0248(6) Uani 1 1 d D . . H6 H 0.6791(9) -0.031(4) -0.0182(15) 0.030 Uiso 1 1 d D . . C1 C 0.19704(12) 0.9948(4) 0.21957(12) 0.0152(6) Uani 1 1 d . . . C2 C 0.25313(12) 1.0786(4) 0.24301(12) 0.0134(6) Uani 1 1 d . . . C3 C 0.29067(12) 1.1430(4) 0.20948(12) 0.0145(6) Uani 1 1 d . . . C4 C 0.33958(12) 1.2185(4) 0.23801(12) 0.0168(6) Uani 1 1 d . . . H4A H 0.3653 1.2669 0.2161 0.020 Uiso 1 1 calc R . . C5 C 0.35213(12) 1.2258(4) 0.29785(13) 0.0168(6) Uani 1 1 d . . . C6 C 0.31297(12) 1.1515(4) 0.32864(12) 0.0156(6) Uani 1 1 d . . . C7 C 0.31504(12) 1.1340(4) 0.39379(12) 0.0175(6) Uani 1 1 d . . . C8 C 0.28196(12) 1.1299(4) 0.14484(12) 0.0172(6) Uani 1 1 d . . . C9 C 0.40881(13) 1.3081(4) 0.32074(13) 0.0205(7) Uani 1 1 d . . . C10 C 0.18990(13) 0.5480(4) 0.10192(13) 0.0194(7) Uani 1 1 d . . . C11 C 0.19110(12) 0.5254(4) 0.16657(12) 0.0168(6) Uani 1 1 d . . . C12 C 0.15201(12) 0.4468(4) 0.19644(13) 0.0191(7) Uani 1 1 d . . . C13 C 0.16388(12) 0.4550(4) 0.25664(13) 0.0174(6) Uani 1 1 d . . . H13 H 0.1379 0.4056 0.2781 0.021 Uiso 1 1 calc R . . C14 C 0.21183(12) 0.5318(4) 0.28604(12) 0.0159(6) Uani 1 1 d . . . C15 C 0.24970(12) 0.5961(4) 0.25308(12) 0.0143(6) Uani 1 1 d . . . C16 C 0.30658(12) 0.6745(4) 0.27666(12) 0.0162(6) Uani 1 1 d . . . C17 C 0.09680(13) 0.3556(5) 0.17256(14) 0.0253(7) Uani 1 1 d . . . C18 C 0.21859(12) 0.5487(4) 0.35112(12) 0.0169(6) Uani 1 1 d . . . C19 C 0.13872(12) 1.0602(4) 0.42979(12) 0.0189(7) Uani 1 1 d . . . H19 H 0.1704 1.0319 0.4574 0.023 Uiso 1 1 calc R . . C20 C 0.09142(12) 1.1169(4) 0.44883(13) 0.0210(7) Uani 1 1 d . . . H20 H 0.0913 1.1296 0.4888 0.025 Uiso 1 1 calc R . . C21 C 0.04362(12) 1.1559(4) 0.40963(12) 0.0178(6) Uani 1 1 d . . . C22 C 0.04667(13) 1.1315(5) 0.35174(13) 0.0257(8) Uani 1 1 d . . . H22 H 0.0149 1.1516 0.3234 0.031 Uiso 1 1 calc R . . C23 C 0.09560(13) 1.0782(5) 0.33562(13) 0.0241(7) Uani 1 1 d . . . H23 H 0.0968 1.0655 0.2958 0.029 Uiso 1 1 calc R . . C24 C -0.00775(12) 1.2252(4) 0.42574(13) 0.0197(7) Uani 1 1 d . . . H24 H -0.0380 1.2464 0.3957 0.024 Uiso 1 1 calc R . . C25 C -0.01536(13) 1.2608(4) 0.47931(13) 0.0193(7) Uani 1 1 d . . . H25 H 0.0143 1.2335 0.5095 0.023 Uiso 1 1 calc R . . C26 C -0.06561(12) 1.3384(4) 0.49537(13) 0.0184(6) Uani 1 1 d . . . C27 C -0.06857(13) 1.3566(4) 0.55403(13) 0.0212(7) Uani 1 1 d . . . H27 H -0.0382 1.3204 0.5823 0.025 Uiso 1 1 calc R . . C28 C -0.11521(14) 1.4264(4) 0.57033(14) 0.0233(7) Uani 1 1 d . . . H28 H -0.1171 1.4384 0.6100 0.028 Uiso 1 1 calc R . . C29 C -0.15659(14) 1.4682(4) 0.47416(14) 0.0245(7) Uani 1 1 d . . . H29 H -0.1872 1.5087 0.4470 0.029 Uiso 1 1 calc R . . C30 C -0.11039(13) 1.3994(4) 0.45564(13) 0.0215(7) Uani 1 1 d . . . H30 H -0.1090 1.3934 0.4157 0.026 Uiso 1 1 calc R . . C31 C 0.35375(12) 0.5263(4) 0.07304(12) 0.0166(6) Uani 1 1 d . . . H31 H 0.3190 0.5265 0.0483 0.020 Uiso 1 1 calc R . . C32 C 0.39792(13) 0.4444(4) 0.05434(13) 0.0208(7) Uani 1 1 d . . . H32 H 0.3934 0.3883 0.0176 0.025 Uiso 1 1 calc R . . C33 C 0.45024(13) 0.4444(5) 0.09037(14) 0.0239(7) Uani 1 1 d . . . C34 C 0.45373(13) 0.5326(4) 0.14303(13) 0.0228(7) Uani 1 1 d . . . H34 H 0.4883 0.5401 0.1681 0.027 Uiso 1 1 calc R . . C35 C 0.40752(12) 0.6084(4) 0.15865(13) 0.0200(7) Uani 1 1 d . . . H35 H 0.4109 0.6653 0.1952 0.024 Uiso 1 1 calc R . . C36 C 0.50013(14) 0.3565(5) 0.07680(14) 0.0269(8) Uani 1 1 d . . . H36 H 0.5315 0.3510 0.1065 0.032 Uiso 1 1 calc R . . C37 C 0.50523(14) 0.2829(5) 0.02581(15) 0.0259(7) Uani 1 1 d . . . H37 H 0.4739 0.2858 -0.0039 0.031 Uiso 1 1 calc R . . C38 C 0.55565(13) 0.1992(4) 0.01324(13) 0.0196(7) Uani 1 1 d . . . C39 C 0.55590(12) 0.1150(4) -0.04035(13) 0.0177(6) Uani 1 1 d . . . H39 H 0.5233 0.1145 -0.0685 0.021 Uiso 1 1 calc R . . C40 C 0.60318(13) 0.0339(4) -0.05185(14) 0.0219(7) Uani 1 1 d . . . H40 H 0.6033 -0.0229 -0.0880 0.026 Uiso 1 1 calc R . . C41 C 0.65069(14) 0.1128(5) 0.03978(14) 0.0267(8) Uani 1 1 d . . . H41 H 0.6839 0.1107 0.0670 0.032 Uiso 1 1 calc R . . C42 C 0.60465(14) 0.1946(5) 0.05315(13) 0.0248(7) Uani 1 1 d . . . H42 H 0.6058 0.2489 0.0898 0.030 Uiso 1 1 calc R . . O17 O 0.74025(9) 0.6857(3) 0.49611(9) 0.0207(5) Uani 1 1 d D . . H17A H 0.7373(14) 0.734(4) 0.4606(9) 0.025 Uiso 1 1 d D . . H17B H 0.7384(14) 0.767(3) 0.5211(10) 0.025 Uiso 1 1 d D . . O18 O 0.43806(11) 0.8799(4) 0.28315(12) 0.0359(6) Uani 1 1 d D . . O19 O 0.06397(10) 0.7908(4) 0.21822(11) 0.0367(6) Uani 1 1 d D . . H19A H 0.0571(13) 0.729(5) 0.2466(11) 0.044 Uiso 1 1 d D . . H19B H 0.0966(7) 0.833(5) 0.2206(14) 0.044 Uiso 1 1 d D . . O20 O 0.97464(10) 0.0843(4) 0.19436(11) 0.0354(6) Uani 1 1 d D . . H20A H 1.0002(10) 0.162(3) 0.1918(17) 0.042 Uiso 1 1 d D . . H20B H 0.9859(13) -0.018(2) 0.2084(16) 0.042 Uiso 1 1 d D . . O21 O 0.53143(11) 0.5781(4) 0.31151(13) 0.0393(7) Uani 1 1 d D . . H21A H 0.5063(10) 0.506(4) 0.3192(17) 0.047 Uiso 1 1 d D . . H21B H 0.5195(13) 0.681(3) 0.2977(17) 0.047 Uiso 1 1 d D . . H18A H 0.4427(16) 0.952(4) 0.2562(12) 0.045(13) Uiso 1 1 d D . . H18B H 0.4057(10) 0.840(8) 0.283(2) 0.13(3) Uiso 1 1 d 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 0.01557(18) 0.0226(2) 0.01122(17) -0.00037(14) 0.00366(13) 0.00003(15) Zn2 0.01700(18) 0.0200(2) 0.01111(17) -0.00005(14) 0.00312(14) 0.00198(14) O1 0.0163(10) 0.0278(12) 0.0118(10) 0.0003(9) 0.0022(8) -0.0031(9) O2 0.0206(11) 0.0353(14) 0.0115(10) -0.0005(10) -0.0008(9) -0.0027(10) O3 0.0263(12) 0.0187(12) 0.0145(10) 0.0009(9) 0.0071(9) 0.0038(9) O4 0.0368(13) 0.0179(12) 0.0129(10) 0.0039(9) 0.0052(10) 0.0061(10) O5 0.0234(12) 0.0534(17) 0.0237(12) -0.0027(12) 0.0053(10) -0.0148(12) O6 0.0209(12) 0.0480(16) 0.0185(11) -0.0022(11) 0.0006(10) -0.0102(11) O7 0.0254(12) 0.0408(15) 0.0124(10) -0.0028(10) -0.0012(9) -0.0084(11) O8 0.0197(11) 0.0220(12) 0.0126(10) 0.0002(9) 0.0033(9) -0.0008(9) O9 0.0249(11) 0.0213(12) 0.0138(10) -0.0016(9) 0.0053(9) 0.0000(9) O10 0.0384(14) 0.0238(13) 0.0159(11) 0.0040(10) 0.0099(10) 0.0083(11) O11 0.0243(13) 0.0543(17) 0.0297(13) 0.0030(12) 0.0028(11) -0.0163(12) O12 0.0252(13) 0.0455(17) 0.0224(12) 0.0002(11) -0.0059(10) -0.0120(12) O13 0.0306(13) 0.0483(16) 0.0161(11) -0.0019(11) -0.0061(10) -0.0121(12) O14 0.0219(11) 0.0247(12) 0.0132(10) 0.0004(9) -0.0002(9) 0.0025(10) O15 0.0159(10) 0.0234(12) 0.0123(10) -0.0004(9) 0.0024(8) -0.0020(9) O16 0.0207(11) 0.0434(15) 0.0114(10) -0.0006(10) -0.0020(9) -0.0031(11) N1 0.0151(12) 0.0150(13) 0.0103(11) -0.0011(10) 0.0020(10) 0.0016(10) N2 0.0155(12) 0.0182(14) 0.0118(11) -0.0027(10) 0.0010(10) 0.0037(10) N3 0.0156(12) 0.0197(14) 0.0130(12) 0.0008(10) 0.0027(10) 0.0013(11) N4 0.0175(13) 0.0247(16) 0.0292(15) -0.0059(12) 0.0094(12) -0.0007(12) N5 0.0192(13) 0.0170(14) 0.0153(12) 0.0006(10) 0.0048(10) 0.0024(11) N6 0.0228(14) 0.0232(16) 0.0290(15) -0.0019(12) 0.0060(13) 0.0065(12) C1 0.0144(14) 0.0190(16) 0.0119(13) -0.0014(12) 0.0012(11) 0.0047(12) C2 0.0150(14) 0.0152(15) 0.0100(13) -0.0010(11) 0.0018(11) 0.0033(12) C3 0.0151(14) 0.0137(15) 0.0148(14) 0.0011(12) 0.0026(12) 0.0032(12) C4 0.0162(14) 0.0191(16) 0.0165(14) 0.0023(12) 0.0063(12) 0.0012(13) C5 0.0169(14) 0.0181(16) 0.0153(14) -0.0007(12) 0.0024(12) 0.0047(12) C6 0.0153(14) 0.0183(16) 0.0127(13) -0.0014(12) 0.0006(12) 0.0040(12) C7 0.0191(15) 0.0194(17) 0.0134(14) 0.0005(12) 0.0013(12) 0.0046(13) C8 0.0141(14) 0.0239(18) 0.0144(14) 0.0003(13) 0.0051(12) 0.0005(13) C9 0.0178(15) 0.0247(18) 0.0182(15) -0.0004(13) 0.0013(13) 0.0002(13) C10 0.0216(16) 0.0217(17) 0.0128(14) 0.0002(12) -0.0030(12) 0.0042(13) C11 0.0174(14) 0.0171(16) 0.0148(14) -0.0029(12) -0.0006(12) 0.0034(12) C12 0.0169(15) 0.0195(17) 0.0195(15) -0.0006(13) -0.0014(12) 0.0019(13) C13 0.0170(14) 0.0180(16) 0.0176(15) 0.0006(12) 0.0044(12) 0.0011(13) C14 0.0180(14) 0.0157(16) 0.0139(14) -0.0001(12) 0.0028(12) 0.0046(12) C15 0.0158(14) 0.0143(15) 0.0127(13) -0.0006(11) 0.0018(11) 0.0054(12) C16 0.0173(14) 0.0196(17) 0.0117(13) -0.0011(12) 0.0023(12) 0.0051(13) C17 0.0199(16) 0.0285(19) 0.0258(17) -0.0025(15) -0.0015(14) -0.0006(15) C18 0.0124(14) 0.0283(19) 0.0112(13) 0.0017(13) 0.0053(11) 0.0029(13) C19 0.0176(15) 0.0248(18) 0.0136(14) -0.0003(13) 0.0004(12) 0.0005(13) C20 0.0199(15) 0.0281(18) 0.0149(14) 0.0013(13) 0.0025(13) 0.0031(14) C21 0.0176(14) 0.0200(17) 0.0155(14) -0.0020(12) 0.0020(12) -0.0012(13) C22 0.0199(16) 0.041(2) 0.0147(15) -0.0024(14) -0.0020(13) 0.0080(15) C23 0.0227(16) 0.036(2) 0.0135(15) -0.0002(14) 0.0024(13) 0.0048(15) C24 0.0157(15) 0.0254(18) 0.0163(14) -0.0003(13) -0.0016(12) 0.0007(13) C25 0.0171(15) 0.0218(17) 0.0189(15) 0.0000(13) 0.0021(12) 0.0010(13) C26 0.0186(15) 0.0176(16) 0.0192(15) -0.0015(13) 0.0037(13) -0.0023(13) C27 0.0204(15) 0.0240(18) 0.0193(15) -0.0029(13) 0.0033(13) -0.0029(14) C28 0.0302(18) 0.0224(18) 0.0181(15) -0.0011(13) 0.0065(14) -0.0054(15) C29 0.0209(16) 0.0261(19) 0.0255(17) -0.0061(14) 0.0008(14) 0.0020(14) C30 0.0219(16) 0.0227(17) 0.0191(15) -0.0050(13) 0.0013(13) 0.0023(14) C31 0.0180(14) 0.0172(16) 0.0138(14) -0.0013(12) 0.0002(12) -0.0023(12) C32 0.0256(17) 0.0230(18) 0.0137(14) -0.0043(13) 0.0032(13) -0.0016(14) C33 0.0197(16) 0.0284(19) 0.0236(17) -0.0051(14) 0.0040(14) 0.0025(14) C34 0.0192(16) 0.0296(19) 0.0181(15) -0.0036(14) -0.0011(13) 0.0060(14) C35 0.0203(15) 0.0240(18) 0.0146(14) -0.0006(13) -0.0008(12) 0.0028(13) C36 0.0250(17) 0.032(2) 0.0230(17) 0.0004(15) 0.0015(14) 0.0009(15) C37 0.0228(17) 0.0255(19) 0.0296(18) -0.0029(15) 0.0047(15) -0.0014(14) C38 0.0264(16) 0.0160(16) 0.0186(15) 0.0012(13) 0.0101(13) 0.0004(13) C39 0.0188(15) 0.0179(16) 0.0170(14) 0.0013(12) 0.0045(12) 0.0004(13) C40 0.0263(17) 0.0201(17) 0.0197(15) -0.0026(13) 0.0048(14) -0.0004(14) C41 0.0292(18) 0.030(2) 0.0182(16) 0.0022(14) -0.0037(14) 0.0051(15) C42 0.0368(19) 0.0268(19) 0.0113(14) -0.0001(13) 0.0051(14) 0.0007(15) O17 0.0265(12) 0.0248(13) 0.0113(10) -0.0006(9) 0.0045(10) 0.0025(10) O18 0.0257(14) 0.0441(18) 0.0358(15) -0.0048(13) -0.0008(12) -0.0088(13) O19 0.0222(13) 0.0447(17) 0.0398(15) 0.0010(13) -0.0042(12) -0.0088(12) O20 0.0334(14) 0.0335(15) 0.0362(15) 0.0048(12) -0.0032(12) -0.0077(12) O21 0.0365(15) 0.0316(16) 0.0475(17) 0.0049(13) 0.0006(13) -0.0096(12) _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 O9 1.959(2) . ? Zn1 N3 2.024(2) . ? Zn1 N1 2.048(2) . ? Zn1 O1 2.133(2) . ? Zn1 O8 2.144(2) . ? Zn2 O3 1.971(2) . ? Zn2 N5 2.025(2) . ? Zn2 N2 2.048(2) . ? Zn2 O14 2.102(2) . ? Zn2 O15 2.132(2) . ? O1 C1 1.276(3) . ? O2 C1 1.232(3) . ? O3 C8 1.284(4) . ? O4 C8 1.228(4) . ? O5 C9 1.216(4) . ? O6 C9 1.291(4) . ? O6 H6A 0.8400 . ? O7 C7 1.262(4) . ? O8 C7 1.250(4) . ? O9 C18 1.269(4) . ? O10 C18 1.235(4) . ? O11 C17 1.211(4) . ? O12 C17 1.301(4) . ? O12 H12 0.8400 . ? O13 C10 1.259(4) . ? O14 C10 1.255(4) . ? O15 C16 1.284(3) . ? O16 C16 1.233(3) . ? N1 C6 1.338(4) . ? N1 C2 1.340(3) . ? N2 C15 1.331(3) . ? N2 C11 1.343(4) . ? N3 C23 1.346(4) . ? N3 C19 1.350(4) . ? N4 C28 1.339(4) . ? N4 C29 1.353(4) . ? N4 H4 0.919(10) . ? N5 C35 1.347(4) . ? N5 C31 1.347(4) . ? N6 C40 1.335(4) . ? N6 C41 1.354(4) . ? N6 H6 0.910(10) . ? C1 C2 1.523(4) . ? C2 C3 1.394(4) . ? C3 C4 1.389(4) . ? C3 C8 1.509(4) . ? C4 C5 1.397(4) . ? C4 H4A 0.9500 . ? C5 C6 1.408(4) . ? C5 C9 1.529(4) . ? C6 C7 1.537(4) . ? C10 C11 1.532(4) . ? C11 C12 1.406(4) . ? C12 C13 1.404(4) . ? C12 C17 1.531(4) . ? C13 C14 1.381(4) . ? C13 H13 0.9500 . ? C14 C15 1.391(4) . ? C14 C18 1.524(4) . ? C15 C16 1.525(4) . ? C19 C20 1.377(4) . ? C19 H19 0.9500 . ? C20 C21 1.396(4) . ? C20 H20 0.9500 . ? C21 C22 1.393(4) . ? C21 C24 1.467(4) . ? C22 C23 1.375(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.336(4) . ? C24 H24 0.9500 . ? C25 C26 1.464(4) . ? C25 H25 0.9500 . ? C26 C30 1.393(4) . ? C26 C27 1.406(4) . ? C27 C28 1.366(4) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.377(4) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.375(4) . ? C31 H31 0.9500 . ? C32 C33 1.415(4) . ? C32 H32 0.9500 . ? C33 C34 1.392(4) . ? C33 C36 1.465(4) . ? C34 C35 1.368(4) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C37 1.345(4) . ? C36 H36 0.9500 . ? C37 C38 1.455(4) . ? C37 H37 0.9500 . ? C38 C42 1.398(4) . ? C38 C39 1.410(4) . ? C39 C40 1.371(4) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C42 1.362(5) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? O17 H17A 0.90(2) . ? O17 H17B 0.845(10) . ? O18 H18A 0.850(10) . ? O18 H18B 0.846(10) . ? O19 H19A 0.848(10) . ? O19 H19B 0.852(10) . ? O20 H20A 0.856(10) . ? O20 H20B 0.852(10) . ? O21 H21A 0.854(10) . ? O21 H21B 0.858(10) . ? 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 O9 Zn1 N3 102.05(9) . . ? O9 Zn1 N1 124.34(9) . . ? N3 Zn1 N1 133.59(10) . . ? O9 Zn1 O1 103.38(9) . . ? N3 Zn1 O1 94.37(9) . . ? N1 Zn1 O1 77.37(9) . . ? O9 Zn1 O8 93.11(9) . . ? N3 Zn1 O8 102.61(9) . . ? N1 Zn1 O8 76.02(9) . . ? O1 Zn1 O8 153.33(8) . . ? O3 Zn2 N5 103.86(9) . . ? O3 Zn2 N2 131.20(9) . . ? N5 Zn2 N2 124.89(10) . . ? O3 Zn2 O14 94.16(9) . . ? N5 Zn2 O14 100.04(9) . . ? N2 Zn2 O14 76.80(9) . . ? O3 Zn2 O15 102.72(8) . . ? N5 Zn2 O15 95.12(9) . . ? N2 Zn2 O15 77.10(9) . . ? O14 Zn2 O15 153.90(8) . . ? C1 O1 Zn1 116.47(18) . . ? C8 O3 Zn2 132.06(19) . . ? C9 O6 H6A 109.5 . . ? C7 O8 Zn1 116.04(18) . . ? C18 O9 Zn1 138.01(19) . . ? C17 O12 H12 109.5 . . ? C10 O14 Zn2 116.45(18) . . ? C16 O15 Zn2 115.97(18) . . ? C6 N1 C2 123.0(3) . . ? C6 N1 Zn1 120.02(19) . . ? C2 N1 Zn1 116.77(19) . . ? C15 N2 C11 123.1(3) . . ? C15 N2 Zn2 117.8(2) . . ? C11 N2 Zn2 118.9(2) . . ? C23 N3 C19 117.2(3) . . ? C23 N3 Zn1 119.6(2) . . ? C19 N3 Zn1 123.1(2) . . ? C28 N4 C29 121.4(3) . . ? C28 N4 H4 121(2) . . ? C29 N4 H4 117(2) . . ? C35 N5 C31 117.4(3) . . ? C35 N5 Zn2 120.1(2) . . ? C31 N5 Zn2 122.5(2) . . ? C40 N6 C41 122.1(3) . . ? C40 N6 H6 120(2) . . ? C41 N6 H6 117(2) . . ? O2 C1 O1 127.4(3) . . ? O2 C1 C2 118.0(3) . . ? O1 C1 C2 114.6(2) . . ? N1 C2 C3 120.5(3) . . ? N1 C2 C1 114.6(2) . . ? C3 C2 C1 124.9(3) . . ? C4 C3 C2 117.3(3) . . ? C4 C3 C8 118.7(3) . . ? C2 C3 C8 123.9(3) . . ? C3 C4 C5 122.2(3) . . ? C3 C4 H4A 118.9 . . ? C5 C4 H4A 118.9 . . ? C4 C5 C6 117.0(3) . . ? C4 C5 C9 114.0(3) . . ? C6 C5 C9 129.0(3) . . ? N1 C6 C5 120.0(3) . . ? N1 C6 C7 110.3(3) . . ? C5 C6 C7 129.7(3) . . ? O8 C7 O7 123.7(3) . . ? O8 C7 C6 117.4(3) . . ? O7 C7 C6 118.8(3) . . ? O4 C8 O3 124.3(3) . . ? O4 C8 C3 118.2(3) . . ? O3 C8 C3 117.3(3) . . ? O5 C9 O6 121.3(3) . . ? O5 C9 C5 118.3(3) . . ? O6 C9 C5 120.3(3) . . ? O14 C10 O13 124.0(3) . . ? O14 C10 C11 117.2(3) . . ? O13 C10 C11 118.8(3) . . ? N2 C11 C12 119.6(3) . . ? N2 C11 C10 110.3(3) . . ? C12 C11 C10 130.1(3) . . ? C13 C12 C11 116.6(3) . . ? C13 C12 C17 114.3(3) . . ? C11 C12 C17 129.0(3) . . ? C14 C13 C12 122.7(3) . . ? C14 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C13 C14 C15 116.7(3) . . ? C13 C14 C18 118.7(3) . . ? C15 C14 C18 124.6(3) . . ? N2 C15 C14 121.1(3) . . ? N2 C15 C16 113.5(3) . . ? C14 C15 C16 125.4(3) . . ? O16 C16 O15 126.5(3) . . ? O16 C16 C15 118.6(3) . . ? O15 C16 C15 114.9(2) . . ? O11 C17 O12 122.5(3) . . ? O11 C17 C12 118.3(3) . . ? O12 C17 C12 119.2(3) . . ? O10 C18 O9 124.4(3) . . ? O10 C18 C14 117.5(3) . . ? O9 C18 C14 117.8(3) . . ? N3 C19 C20 122.6(3) . . ? N3 C19 H19 118.7 . . ? C20 C19 H19 118.7 . . ? C19 C20 C21 120.3(3) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C20 116.6(3) . . ? C22 C21 C24 119.3(3) . . ? C20 C21 C24 124.1(3) . . ? C23 C22 C21 120.1(3) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? N3 C23 C22 123.1(3) . . ? N3 C23 H23 118.4 . . ? C22 C23 H23 118.4 . . ? C25 C24 C21 125.2(3) . . ? C25 C24 H24 117.4 . . ? C21 C24 H24 117.4 . . ? C24 C25 C26 125.4(3) . . ? C24 C25 H25 117.3 . . ? C26 C25 H25 117.3 . . ? C30 C26 C27 117.9(3) . . ? C30 C26 C25 123.6(3) . . ? C27 C26 C25 118.5(3) . . ? C28 C27 C26 119.8(3) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? N4 C28 C27 120.8(3) . . ? N4 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? N4 C29 C30 120.0(3) . . ? N4 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C29 C30 C26 120.1(3) . . ? C29 C30 H30 120.0 . . ? C26 C30 H30 120.0 . . ? N5 C31 C32 123.1(3) . . ? N5 C31 H31 118.5 . . ? C32 C31 H31 118.5 . . ? C31 C32 C33 119.3(3) . . ? C31 C32 H32 120.3 . . ? C33 C32 H32 120.3 . . ? C34 C33 C32 116.8(3) . . ? C34 C33 C36 118.2(3) . . ? C32 C33 C36 125.0(3) . . ? C35 C34 C33 120.1(3) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? N5 C35 C34 123.3(3) . . ? N5 C35 H35 118.3 . . ? C34 C35 H35 118.3 . . ? C37 C36 C33 125.4(3) . . ? C37 C36 H36 117.3 . . ? C33 C36 H36 117.3 . . ? C36 C37 C38 124.2(3) . . ? C36 C37 H37 117.9 . . ? C38 C37 H37 117.9 . . ? C42 C38 C39 117.6(3) . . ? C42 C38 C37 122.4(3) . . ? C39 C38 C37 120.0(3) . . ? C40 C39 C38 120.0(3) . . ? C40 C39 H39 120.0 . . ? C38 C39 H39 120.0 . . ? N6 C40 C39 120.1(3) . . ? N6 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? N6 C41 C42 119.9(3) . . ? N6 C41 H41 120.0 . . ? C42 C41 H41 120.0 . . ? C41 C42 C38 120.4(3) . . ? C41 C42 H42 119.8 . . ? C38 C42 H42 119.8 . . ? H17A O17 H17B 112(2) . . ? H18A O18 H18B 117.6(19) . . ? H19A O19 H19B 116.7(18) . . ? H20A O20 H20B 114.9(17) . . ? H21A O21 H21B 114.6(18) . . ? 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 O9 Zn1 O1 C1 -120.8(2) . . . . ? N3 Zn1 O1 C1 135.7(2) . . . . ? N1 Zn1 O1 C1 1.9(2) . . . . ? O8 Zn1 O1 C1 5.9(3) . . . . ? N5 Zn2 O3 C8 -142.1(3) . . . . ? N2 Zn2 O3 C8 40.4(3) . . . . ? O14 Zn2 O3 C8 116.5(3) . . . . ? O15 Zn2 O3 C8 -43.5(3) . . . . ? O9 Zn1 O8 C7 123.7(2) . . . . ? N3 Zn1 O8 C7 -133.2(2) . . . . ? N1 Zn1 O8 C7 -1.0(2) . . . . ? O1 Zn1 O8 C7 -5.0(3) . . . . ? N3 Zn1 O9 C18 119.7(3) . . . . ? N1 Zn1 O9 C18 -61.5(3) . . . . ? O1 Zn1 O9 C18 22.2(3) . . . . ? O8 Zn1 O9 C18 -136.7(3) . . . . ? O3 Zn2 O14 C10 -134.4(2) . . . . ? N5 Zn2 O14 C10 120.8(2) . . . . ? N2 Zn2 O14 C10 -3.0(2) . . . . ? O15 Zn2 O14 C10 -3.8(3) . . . . ? O3 Zn2 O15 C16 132.0(2) . . . . ? N5 Zn2 O15 C16 -122.5(2) . . . . ? N2 Zn2 O15 C16 2.2(2) . . . . ? O14 Zn2 O15 C16 3.0(3) . . . . ? O9 Zn1 N1 C6 -80.7(2) . . . . ? N3 Zn1 N1 C6 97.7(2) . . . . ? O1 Zn1 N1 C6 -178.4(2) . . . . ? O8 Zn1 N1 C6 3.4(2) . . . . ? O9 Zn1 N1 C2 93.6(2) . . . . ? N3 Zn1 N1 C2 -88.1(2) . . . . ? O1 Zn1 N1 C2 -4.1(2) . . . . ? O8 Zn1 N1 C2 177.7(2) . . . . ? O3 Zn2 N2 C15 -92.0(2) . . . . ? N5 Zn2 N2 C15 91.0(2) . . . . ? O14 Zn2 N2 C15 -175.9(2) . . . . ? O15 Zn2 N2 C15 3.7(2) . . . . ? O3 Zn2 N2 C11 82.5(2) . . . . ? N5 Zn2 N2 C11 -94.6(2) . . . . ? O14 Zn2 N2 C11 -1.4(2) . . . . ? O15 Zn2 N2 C11 178.2(2) . . . . ? O9 Zn1 N3 C23 -111.7(2) . . . . ? N1 Zn1 N3 C23 69.7(3) . . . . ? O1 Zn1 N3 C23 -7.0(2) . . . . ? O8 Zn1 N3 C23 152.3(2) . . . . ? O9 Zn1 N3 C19 65.8(3) . . . . ? N1 Zn1 N3 C19 -112.8(2) . . . . ? O1 Zn1 N3 C19 170.5(2) . . . . ? O8 Zn1 N3 C19 -30.2(3) . . . . ? O3 Zn2 N5 C35 91.0(2) . . . . ? N2 Zn2 N5 C35 -91.3(2) . . . . ? O14 Zn2 N5 C35 -172.1(2) . . . . ? O15 Zn2 N5 C35 -13.4(2) . . . . ? O3 Zn2 N5 C31 -87.9(2) . . . . ? N2 Zn2 N5 C31 89.8(2) . . . . ? O14 Zn2 N5 C31 9.0(2) . . . . ? O15 Zn2 N5 C31 167.7(2) . . . . ? Zn1 O1 C1 O2 -179.6(3) . . . . ? Zn1 O1 C1 C2 0.3(3) . . . . ? C6 N1 C2 C3 0.8(4) . . . . ? Zn1 N1 C2 C3 -173.3(2) . . . . ? C6 N1 C2 C1 179.6(3) . . . . ? Zn1 N1 C2 C1 5.5(3) . . . . ? O2 C1 C2 N1 176.2(3) . . . . ? O1 C1 C2 N1 -3.8(4) . . . . ? O2 C1 C2 C3 -5.2(4) . . . . ? O1 C1 C2 C3 174.9(3) . . . . ? N1 C2 C3 C4 -2.6(4) . . . . ? C1 C2 C3 C4 178.8(3) . . . . ? N1 C2 C3 C8 175.4(3) . . . . ? C1 C2 C3 C8 -3.2(5) . . . . ? C2 C3 C4 C5 1.9(4) . . . . ? C8 C3 C4 C5 -176.2(3) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C3 C4 C5 C9 178.0(3) . . . . ? C2 N1 C6 C5 1.7(4) . . . . ? Zn1 N1 C6 C5 175.6(2) . . . . ? C2 N1 C6 C7 -178.7(3) . . . . ? Zn1 N1 C6 C7 -4.8(3) . . . . ? C4 C5 C6 N1 -2.2(4) . . . . ? C9 C5 C6 N1 -179.3(3) . . . . ? C4 C5 C6 C7 178.2(3) . . . . ? C9 C5 C6 C7 1.1(5) . . . . ? Zn1 O8 C7 O7 178.5(2) . . . . ? Zn1 O8 C7 C6 -1.2(3) . . . . ? N1 C6 C7 O8 3.8(4) . . . . ? C5 C6 C7 O8 -176.6(3) . . . . ? N1 C6 C7 O7 -175.9(3) . . . . ? C5 C6 C7 O7 3.7(5) . . . . ? Zn2 O3 C8 O4 -158.7(2) . . . . ? Zn2 O3 C8 C3 26.8(4) . . . . ? C4 C3 C8 O4 -76.9(4) . . . . ? C2 C3 C8 O4 105.2(4) . . . . ? C4 C3 C8 O3 98.0(3) . . . . ? C2 C3 C8 O3 -80.0(4) . . . . ? C4 C5 C9 O5 1.7(4) . . . . ? C6 C5 C9 O5 178.9(3) . . . . ? C4 C5 C9 O6 -177.8(3) . . . . ? C6 C5 C9 O6 -0.6(5) . . . . ? Zn2 O14 C10 O13 -175.1(3) . . . . ? Zn2 O14 C10 C11 6.3(3) . . . . ? C15 N2 C11 C12 -1.4(4) . . . . ? Zn2 N2 C11 C12 -175.5(2) . . . . ? C15 N2 C11 C10 178.8(3) . . . . ? Zn2 N2 C11 C10 4.6(3) . . . . ? O14 C10 C11 N2 -7.2(4) . . . . ? O13 C10 C11 N2 174.2(3) . . . . ? O14 C10 C11 C12 173.0(3) . . . . ? O13 C10 C11 C12 -5.7(5) . . . . ? N2 C11 C12 C13 3.4(4) . . . . ? C10 C11 C12 C13 -176.8(3) . . . . ? N2 C11 C12 C17 -178.1(3) . . . . ? C10 C11 C12 C17 1.7(5) . . . . ? C11 C12 C13 C14 -1.4(5) . . . . ? C17 C12 C13 C14 179.8(3) . . . . ? C12 C13 C14 C15 -2.4(4) . . . . ? C12 C13 C14 C18 174.8(3) . . . . ? C11 N2 C15 C14 -2.8(4) . . . . ? Zn2 N2 C15 C14 171.5(2) . . . . ? C11 N2 C15 C16 177.6(3) . . . . ? Zn2 N2 C15 C16 -8.1(3) . . . . ? C13 C14 C15 N2 4.5(4) . . . . ? C18 C14 C15 N2 -172.4(3) . . . . ? C13 C14 C15 C16 -175.9(3) . . . . ? C18 C14 C15 C16 7.1(5) . . . . ? Zn2 O15 C16 O16 172.6(3) . . . . ? Zn2 O15 C16 C15 -6.9(3) . . . . ? N2 C15 C16 O16 -169.6(3) . . . . ? C14 C15 C16 O16 10.8(5) . . . . ? N2 C15 C16 O15 9.9(4) . . . . ? C14 C15 C16 O15 -169.7(3) . . . . ? C13 C12 C17 O11 1.5(5) . . . . ? C11 C12 C17 O11 -177.0(3) . . . . ? C13 C12 C17 O12 179.9(3) . . . . ? C11 C12 C17 O12 1.4(5) . . . . ? Zn1 O9 C18 O10 -174.6(2) . . . . ? Zn1 O9 C18 C14 -0.9(4) . . . . ? C13 C14 C18 O10 62.8(4) . . . . ? C15 C14 C18 O10 -120.3(3) . . . . ? C13 C14 C18 O9 -111.3(3) . . . . ? C15 C14 C18 O9 65.6(4) . . . . ? C23 N3 C19 C20 -2.3(5) . . . . ? Zn1 N3 C19 C20 -179.8(2) . . . . ? N3 C19 C20 C21 1.4(5) . . . . ? C19 C20 C21 C22 1.0(5) . . . . ? C19 C20 C21 C24 -177.0(3) . . . . ? C20 C21 C22 C23 -2.4(5) . . . . ? C24 C21 C22 C23 175.7(3) . . . . ? C19 N3 C23 C22 0.8(5) . . . . ? Zn1 N3 C23 C22 178.4(3) . . . . ? C21 C22 C23 N3 1.6(6) . . . . ? C22 C21 C24 C25 -177.5(3) . . . . ? C20 C21 C24 C25 0.4(5) . . . . ? C21 C24 C25 C26 176.8(3) . . . . ? C24 C25 C26 C30 -5.7(5) . . . . ? C24 C25 C26 C27 175.8(3) . . . . ? C30 C26 C27 C28 2.3(5) . . . . ? C25 C26 C27 C28 -179.2(3) . . . . ? C29 N4 C28 C27 -2.0(5) . . . . ? C26 C27 C28 N4 -0.1(5) . . . . ? C28 N4 C29 C30 1.7(5) . . . . ? N4 C29 C30 C26 0.6(5) . . . . ? C27 C26 C30 C29 -2.5(5) . . . . ? C25 C26 C30 C29 179.0(3) . . . . ? C35 N5 C31 C32 1.6(4) . . . . ? Zn2 N5 C31 C32 -179.5(2) . . . . ? N5 C31 C32 C33 -0.7(5) . . . . ? C31 C32 C33 C34 -1.2(5) . . . . ? C31 C32 C33 C36 177.6(3) . . . . ? C32 C33 C34 C35 2.2(5) . . . . ? C36 C33 C34 C35 -176.7(3) . . . . ? C31 N5 C35 C34 -0.5(5) . . . . ? Zn2 N5 C35 C34 -179.5(2) . . . . ? C33 C34 C35 N5 -1.4(5) . . . . ? C34 C33 C36 C37 -172.6(3) . . . . ? C32 C33 C36 C37 8.6(6) . . . . ? C33 C36 C37 C38 178.9(3) . . . . ? C36 C37 C38 C42 -2.7(5) . . . . ? C36 C37 C38 C39 175.8(3) . . . . ? C42 C38 C39 C40 -0.5(4) . . . . ? C37 C38 C39 C40 -179.1(3) . . . . ? C41 N6 C40 C39 0.4(5) . . . . ? C38 C39 C40 N6 0.0(5) . . . . ? C40 N6 C41 C42 -0.2(5) . . . . ? N6 C41 C42 C38 -0.3(5) . . . . ? C39 C38 C42 C41 0.6(5) . . . . ? C37 C38 C42 C41 179.2(3) . . . . ? 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 N4 H4 O10 0.919(10) 2.18(2) 2.925(3) 137(3) 3_576 N4 H4 O17 0.919(10) 2.22(3) 2.916(4) 132(3) 1_465 N6 H6 O17 0.910(10) 1.867(16) 2.741(4) 160(3) 4_565 O21 H21A O5 0.854(10) 2.04(2) 2.790(3) 146(4) 1_545 O17 H17A O4 0.90(2) 1.83(2) 2.707(3) 165(3) 2_645 O17 H17B O8 0.845(10) 2.155(11) 2.992(3) 171(3) 3_676 O19 H19A O20 0.848(10) 2.013(11) 2.849(4) 169(3) 2_655 O18 H18A O21 0.850(10) 2.040(14) 2.871(4) 166(4) 2_655 O20 H20A O11 0.856(10) 1.941(15) 2.772(3) 164(3) 1_655 O20 H20B O19 0.852(10) 2.35(2) 3.058(4) 141(3) 1_645 O6 H6A O7 0.84 1.60 2.436(3) 173.7 . O12 H12 O13 0.84 1.60 2.426(3) 169.2 . O19 H19B O1 0.852(10) 2.022(17) 2.831(3) 158(3) . O18 H18B O15 0.846(10) 2.05(3) 2.814(3) 150(5) . O21 H21B O18 0.858(10) 2.45(2) 3.177(4) 143(3) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.325 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 972278' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H16 N4 O8 Zn2' _chemical_formula_weight 655.18 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' 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 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 8.5377(17) _cell_length_b 16.953(3) _cell_length_c 17.256(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.99(3) _cell_angle_gamma 90.00 _cell_volume 2433.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7242 _cell_measurement_theta_min 2.4028 _cell_measurement_theta_max 27.9304 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 2.035 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6864 _exptl_absorpt_correction_T_max 0.7923 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21703 _diffrn_reflns_av_R_equivalents 0.0724 _diffrn_reflns_av_sigmaI/netI 0.0764 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.89 _reflns_number_total 5784 _reflns_number_gt 4289 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0388P)^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 CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5784 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0877 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.002 _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 0.61389(4) 0.33608(2) 0.95263(2) 0.01659(10) Uani 1 1 d . . . Zn2 Zn 0.15439(4) 0.38010(2) 1.102752(19) 0.01400(10) Uani 1 1 d . . . O1 O 0.7405(2) 0.35547(13) 0.86508(12) 0.0198(5) Uani 1 1 d . . . O2 O 0.7775(2) 0.45117(13) 0.78041(11) 0.0199(5) Uani 1 1 d . . . O3 O 0.5305(2) 0.58319(13) 0.68489(12) 0.0221(5) Uani 1 1 d . . . O4 O 0.7078(2) 0.62787(12) 0.79109(12) 0.0178(5) Uani 1 1 d . . . O5 O 0.2011(2) 0.63336(13) 0.96152(12) 0.0200(5) Uani 1 1 d . . . O6 O 0.0305(2) 0.56038(12) 0.87530(12) 0.0168(4) Uani 1 1 d . . . O7 O 0.2095(2) 0.44201(12) 1.01577(12) 0.0166(4) Uani 1 1 d . . . O8 O 0.4056(2) 0.35519(12) 1.01162(12) 0.0177(5) Uani 1 1 d . . . N1 N 0.4963(3) 0.43107(14) 0.89862(13) 0.0128(5) Uani 1 1 d . . . N2 N 0.5717(3) 0.22128(15) 0.93634(14) 0.0175(5) Uani 1 1 d . . . N3 N 0.2210(3) -0.27317(17) 0.72374(16) 0.0266(6) Uani 1 1 d . . . N4 N 0.1212(3) 0.26404(15) 1.07577(14) 0.0154(5) Uani 1 1 d . . . C1 C 0.7086(3) 0.42068(19) 0.82865(17) 0.0163(6) Uani 1 1 d . . . C2 C 0.5649(3) 0.46574(18) 0.84532(16) 0.0146(6) Uani 1 1 d . . . C3 C 0.5085(3) 0.53777(18) 0.81165(16) 0.0143(6) Uani 1 1 d . . . C4 C 0.3759(3) 0.57012(18) 0.83314(17) 0.0164(6) Uani 1 1 d . . . H4 H 0.3314 0.6178 0.8088 0.020 Uiso 1 1 calc R . . C5 C 0.3056(3) 0.53405(17) 0.89008(16) 0.0145(6) Uani 1 1 d . . . C6 C 0.3714(3) 0.46373(18) 0.92252(16) 0.0142(6) Uani 1 1 d . . . C7 C 0.5891(3) 0.58461(18) 0.75641(17) 0.0156(6) Uani 1 1 d . . . C8 C 0.1695(3) 0.57749(17) 0.91221(17) 0.0154(6) Uani 1 1 d . . . C9 C 0.3243(3) 0.41589(18) 0.98787(16) 0.0143(6) Uani 1 1 d . . . C10 C 0.6228(3) 0.18290(19) 0.87784(17) 0.0184(7) Uani 1 1 d . . . H10 H 0.6956 0.2092 0.8523 0.022 Uiso 1 1 calc R . . C11 C 0.5748(3) 0.10806(18) 0.85362(18) 0.0192(7) Uani 1 1 d . . . H11 H 0.6164 0.0829 0.8133 0.023 Uiso 1 1 calc R . . C12 C 0.4644(4) 0.06909(19) 0.88851(18) 0.0203(7) Uani 1 1 d . . . C13 C 0.4178(4) 0.1078(2) 0.95126(19) 0.0251(8) Uani 1 1 d . . . H13 H 0.3482 0.0822 0.9791 0.030 Uiso 1 1 calc R . . C14 C 0.4717(4) 0.18243(19) 0.97278(19) 0.0230(7) Uani 1 1 d . . . H14 H 0.4370 0.2077 1.0151 0.028 Uiso 1 1 calc R . . C15 C 0.3933(4) -0.00726(19) 0.86212(19) 0.0231(7) Uani 1 1 d . . . H15 H 0.3264 -0.0310 0.8927 0.028 Uiso 1 1 calc R . . C16 C 0.4150(4) -0.04612(19) 0.79840(18) 0.0213(7) Uani 1 1 d . . . H16 H 0.4822 -0.0226 0.7678 0.026 Uiso 1 1 calc R . . C17 C 0.3430(4) -0.12242(19) 0.77221(18) 0.0207(7) Uani 1 1 d . . . C18 C 0.4045(4) -0.1674(2) 0.71821(19) 0.0232(7) Uani 1 1 d . . . H18 H 0.4889 -0.1473 0.6962 0.028 Uiso 1 1 calc R . . C19 C 0.3418(4) -0.2411(2) 0.69712(19) 0.0251(7) Uani 1 1 d . . . H19 H 0.3875 -0.2711 0.6613 0.030 Uiso 1 1 calc R . . C20 C 0.1600(4) -0.2288(2) 0.7732(2) 0.0294(8) Uani 1 1 d . . . H20 H 0.0724 -0.2497 0.7922 0.035 Uiso 1 1 calc R . . C21 C 0.2139(4) -0.1550(2) 0.7990(2) 0.0274(8) Uani 1 1 d . . . H21 H 0.1645 -0.1264 0.8344 0.033 Uiso 1 1 calc R . . C22 C 0.0340(3) 0.23849(18) 1.00421(17) 0.0164(6) Uani 1 1 d . . . H22 H -0.0109 0.2765 0.9650 0.020 Uiso 1 1 calc R . . C23 C 0.0083(3) 0.15960(18) 0.98643(17) 0.0172(6) Uani 1 1 d . . . H23 H -0.0517 0.1440 0.9355 0.021 Uiso 1 1 calc R . . C24 C 0.0716(3) 0.10219(18) 1.04409(17) 0.0157(6) Uani 1 1 d . . . C25 C 0.1633(4) 0.12957(19) 1.11662(18) 0.0198(7) Uani 1 1 d . . . H25 H 0.2103 0.0931 1.1570 0.024 Uiso 1 1 calc R . . C26 C 0.1854(3) 0.20936(18) 1.12948(17) 0.0177(6) Uani 1 1 d . . . H26 H 0.2494 0.2264 1.1790 0.021 Uiso 1 1 calc R . . C27 C 0.0441(3) 0.01704(19) 1.03260(17) 0.0184(6) Uani 1 1 d . . . H27 H 0.0933 -0.0167 1.0751 0.022 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 Zn1 0.01596(19) 0.0163(2) 0.01826(18) -0.00153(15) 0.00548(14) 0.00136(14) Zn2 0.01346(18) 0.01478(19) 0.01517(17) -0.00030(14) 0.00618(14) 0.00020(14) O1 0.0180(11) 0.0189(12) 0.0254(11) -0.0013(10) 0.0109(9) 0.0031(9) O2 0.0176(11) 0.0261(13) 0.0187(10) -0.0025(10) 0.0097(9) -0.0012(9) O3 0.0231(12) 0.0297(13) 0.0146(10) 0.0012(10) 0.0064(9) 0.0001(10) O4 0.0184(11) 0.0196(12) 0.0168(10) 0.0021(9) 0.0067(9) -0.0008(9) O5 0.0157(11) 0.0230(13) 0.0207(11) -0.0073(10) 0.0025(9) 0.0019(9) O6 0.0103(10) 0.0215(12) 0.0196(10) -0.0041(9) 0.0056(8) -0.0010(9) O7 0.0168(10) 0.0168(11) 0.0185(10) 0.0001(9) 0.0091(9) 0.0012(9) O8 0.0197(11) 0.0162(11) 0.0189(10) 0.0016(9) 0.0081(9) 0.0021(9) N1 0.0102(11) 0.0150(13) 0.0146(11) -0.0034(10) 0.0059(10) -0.0010(10) N2 0.0171(13) 0.0180(14) 0.0183(12) -0.0010(11) 0.0057(10) 0.0017(11) N3 0.0265(15) 0.0232(16) 0.0315(15) -0.0020(13) 0.0096(13) -0.0034(12) N4 0.0149(12) 0.0152(14) 0.0181(12) 0.0023(11) 0.0077(10) 0.0030(10) C1 0.0135(14) 0.0210(17) 0.0145(14) -0.0062(13) 0.0036(12) -0.0003(13) C2 0.0112(14) 0.0206(17) 0.0117(13) -0.0046(12) 0.0019(11) -0.0022(12) C3 0.0147(14) 0.0191(16) 0.0094(12) -0.0023(12) 0.0033(11) -0.0022(12) C4 0.0140(14) 0.0181(17) 0.0177(14) 0.0000(13) 0.0048(12) 0.0003(12) C5 0.0141(14) 0.0161(16) 0.0127(13) -0.0023(12) 0.0017(11) -0.0010(12) C6 0.0118(14) 0.0179(16) 0.0130(13) -0.0041(12) 0.0032(11) -0.0039(12) C7 0.0120(14) 0.0208(17) 0.0150(14) 0.0011(13) 0.0049(12) 0.0064(12) C8 0.0196(16) 0.0140(16) 0.0150(13) 0.0041(12) 0.0090(12) 0.0015(13) C9 0.0139(14) 0.0162(16) 0.0134(13) -0.0048(12) 0.0040(12) -0.0042(12) C10 0.0141(15) 0.0212(18) 0.0212(15) 0.0000(13) 0.0070(13) 0.0004(13) C11 0.0183(15) 0.0193(17) 0.0219(15) -0.0024(13) 0.0085(13) 0.0023(13) C12 0.0210(16) 0.0173(17) 0.0240(16) -0.0002(14) 0.0081(13) 0.0013(13) C13 0.0303(18) 0.0237(19) 0.0264(17) 0.0002(15) 0.0177(15) -0.0010(15) C14 0.0270(18) 0.0223(18) 0.0228(16) -0.0004(14) 0.0120(14) 0.0033(14) C15 0.0260(17) 0.0192(18) 0.0280(16) 0.0027(14) 0.0141(14) -0.0018(14) C16 0.0173(16) 0.0224(18) 0.0260(16) 0.0038(14) 0.0088(13) 0.0002(13) C17 0.0178(16) 0.0214(18) 0.0215(15) 0.0029(14) 0.0017(13) -0.0014(13) C18 0.0182(16) 0.0270(19) 0.0256(16) -0.0012(15) 0.0076(14) -0.0018(14) C19 0.0252(17) 0.0258(19) 0.0259(16) -0.0032(15) 0.0091(14) 0.0004(15) C20 0.0283(18) 0.028(2) 0.0353(19) -0.0007(17) 0.0153(16) -0.0088(16) C21 0.0247(17) 0.029(2) 0.0334(18) -0.0053(16) 0.0168(16) -0.0020(15) C22 0.0169(15) 0.0194(17) 0.0140(13) 0.0021(12) 0.0054(12) 0.0034(13) C23 0.0194(15) 0.0156(16) 0.0177(14) -0.0022(13) 0.0067(12) -0.0004(13) C24 0.0150(15) 0.0167(16) 0.0173(14) 0.0017(12) 0.0079(12) 0.0015(12) C25 0.0229(16) 0.0194(17) 0.0176(14) 0.0033(13) 0.0057(13) 0.0025(13) C26 0.0166(15) 0.0209(17) 0.0146(14) 0.0017(13) 0.0011(12) 0.0013(13) C27 0.0223(16) 0.0184(16) 0.0156(13) 0.0041(13) 0.0066(12) 0.0033(13) _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 O5 1.976(2) 3_667 ? Zn1 N2 1.988(3) . ? Zn1 N1 2.012(2) . ? Zn1 O1 2.072(2) . ? Zn1 O8 2.2623(19) . ? Zn2 O4 1.947(2) 3_667 ? Zn2 O7 1.9732(19) . ? Zn2 O6 1.9802(19) 3_567 ? Zn2 N4 2.027(3) . ? O1 C1 1.271(4) . ? O2 C1 1.235(3) . ? O3 C7 1.223(3) . ? O4 C7 1.285(4) . ? O4 Zn2 1.947(2) 3_667 ? O5 C8 1.261(4) . ? O5 Zn1 1.976(2) 3_667 ? O6 C8 1.248(4) . ? O6 Zn2 1.9802(19) 3_567 ? O7 C9 1.265(3) . ? O8 C9 1.258(3) . ? N1 C2 1.333(3) . ? N1 C6 1.346(3) . ? N2 C14 1.341(4) . ? N2 C10 1.353(4) . ? N3 C20 1.329(4) . ? N3 C19 1.336(4) . ? N4 C26 1.338(4) . ? N4 C22 1.361(4) . ? C1 C2 1.527(4) . ? C2 C3 1.391(4) . ? C3 C4 1.382(4) . ? C3 C7 1.519(4) . ? C4 C5 1.402(4) . ? C4 H4 0.9500 . ? C5 C6 1.382(4) . ? C5 C8 1.496(4) . ? C6 C9 1.515(4) . ? C10 C11 1.369(4) . ? C10 H10 0.9500 . ? C11 C12 1.393(4) . ? C11 H11 0.9500 . ? C12 C13 1.399(4) . ? C12 C15 1.459(4) . ? C13 C14 1.368(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.330(4) . ? C15 H15 0.9500 . ? C16 C17 1.460(4) . ? C16 H16 0.9500 . ? C17 C18 1.395(4) . ? C17 C21 1.400(4) . ? C18 C19 1.375(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.372(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.379(4) . ? C22 H22 0.9500 . ? C23 C24 1.410(4) . ? C23 H23 0.9500 . ? C24 C25 1.398(4) . ? C24 C27 1.469(4) . ? C25 C26 1.377(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C27 1.337(6) 3_557 ? C27 H27 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 O5 Zn1 N2 116.85(10) 3_667 . ? O5 Zn1 N1 111.64(9) 3_667 . ? N2 Zn1 N1 131.48(10) . . ? O5 Zn1 O1 92.58(9) 3_667 . ? N2 Zn1 O1 99.21(9) . . ? N1 Zn1 O1 79.81(8) . . ? O5 Zn1 O8 101.63(8) 3_667 . ? N2 Zn1 O8 93.90(8) . . ? N1 Zn1 O8 74.52(8) . . ? O1 Zn1 O8 153.79(8) . . ? O4 Zn2 O7 123.77(8) 3_667 . ? O4 Zn2 O6 101.22(8) 3_667 3_567 ? O7 Zn2 O6 102.18(8) . 3_567 ? O4 Zn2 N4 99.93(10) 3_667 . ? O7 Zn2 N4 112.73(9) . . ? O6 Zn2 N4 117.54(9) 3_567 . ? C1 O1 Zn1 114.18(17) . . ? C7 O4 Zn2 130.19(19) . 3_667 ? C8 O5 Zn1 135.8(2) . 3_667 ? C8 O6 Zn2 119.42(18) . 3_567 ? C9 O7 Zn2 116.15(19) . . ? C9 O8 Zn1 113.76(17) . . ? C2 N1 C6 122.1(3) . . ? C2 N1 Zn1 114.95(19) . . ? C6 N1 Zn1 122.30(19) . . ? C14 N2 C10 117.4(3) . . ? C14 N2 Zn1 121.9(2) . . ? C10 N2 Zn1 119.8(2) . . ? C20 N3 C19 115.8(3) . . ? C26 N4 C22 117.6(3) . . ? C26 N4 Zn2 119.9(2) . . ? C22 N4 Zn2 122.5(2) . . ? O2 C1 O1 128.0(3) . . ? O2 C1 C2 116.2(3) . . ? O1 C1 C2 115.7(2) . . ? N1 C2 C3 120.8(2) . . ? N1 C2 C1 113.9(3) . . ? C3 C2 C1 125.3(2) . . ? C4 C3 C2 117.6(3) . . ? C4 C3 C7 118.4(3) . . ? C2 C3 C7 124.0(2) . . ? C3 C4 C5 121.4(3) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 117.5(3) . . ? C6 C5 C8 126.2(2) . . ? C4 C5 C8 116.3(3) . . ? N1 C6 C5 120.6(2) . . ? N1 C6 C9 111.7(3) . . ? C5 C6 C9 127.7(2) . . ? O3 C7 O4 125.6(3) . . ? O3 C7 C3 118.9(3) . . ? O4 C7 C3 115.3(2) . . ? O6 C8 O5 123.6(3) . . ? O6 C8 C5 117.3(3) . . ? O5 C8 C5 118.8(3) . . ? O8 C9 O7 125.5(3) . . ? O8 C9 C6 117.4(2) . . ? O7 C9 C6 117.0(3) . . ? N2 C10 C11 123.3(3) . . ? N2 C10 H10 118.4 . . ? C11 C10 H10 118.4 . . ? C10 C11 C12 119.5(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 116.7(3) . . ? C11 C12 C15 124.1(3) . . ? C13 C12 C15 119.2(3) . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? N2 C14 C13 122.5(3) . . ? N2 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C16 C15 C12 124.9(3) . . ? C16 C15 H15 117.6 . . ? C12 C15 H15 117.6 . . ? C15 C16 C17 124.6(3) . . ? C15 C16 H16 117.7 . . ? C17 C16 H16 117.7 . . ? C18 C17 C21 116.5(3) . . ? C18 C17 C16 119.7(3) . . ? C21 C17 C16 123.7(3) . . ? C19 C18 C17 119.4(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? N3 C19 C18 124.3(3) . . ? N3 C19 H19 117.9 . . ? C18 C19 H19 117.9 . . ? N3 C20 C21 125.0(3) . . ? N3 C20 H20 117.5 . . ? C21 C20 H20 117.5 . . ? C20 C21 C17 119.0(3) . . ? C20 C21 H21 120.5 . . ? C17 C21 H21 120.5 . . ? N4 C22 C23 122.5(3) . . ? N4 C22 H22 118.7 . . ? C23 C22 H22 118.7 . . ? C22 C23 C24 119.8(3) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C25 C24 C23 116.8(3) . . ? C25 C24 C27 119.2(3) . . ? C23 C24 C27 124.0(3) . . ? C26 C25 C24 120.0(3) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? N4 C26 C25 123.3(3) . . ? N4 C26 H26 118.3 . . ? C25 C26 H26 118.3 . . ? C27 C27 C24 125.5(4) 3_557 . ? C27 C27 H27 117.2 3_557 . ? C24 C27 H27 117.2 . . ? 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 O5 Zn1 O1 C1 -100.8(2) 3_667 . . . ? N2 Zn1 O1 C1 141.5(2) . . . . ? N1 Zn1 O1 C1 10.7(2) . . . . ? O8 Zn1 O1 C1 22.4(3) . . . . ? O4 Zn2 O7 C9 69.0(2) 3_667 . . . ? O6 Zn2 O7 C9 -178.43(19) 3_567 . . . ? N4 Zn2 O7 C9 -51.3(2) . . . . ? O5 Zn1 O8 C9 105.4(2) 3_667 . . . ? N2 Zn1 O8 C9 -136.2(2) . . . . ? N1 Zn1 O8 C9 -4.08(19) . . . . ? O1 Zn1 O8 C9 -16.1(3) . . . . ? O5 Zn1 N1 C2 79.4(2) 3_667 . . . ? N2 Zn1 N1 C2 -102.6(2) . . . . ? O1 Zn1 N1 C2 -9.31(19) . . . . ? O8 Zn1 N1 C2 176.0(2) . . . . ? O5 Zn1 N1 C6 -91.4(2) 3_667 . . . ? N2 Zn1 N1 C6 86.5(2) . . . . ? O1 Zn1 N1 C6 179.8(2) . . . . ? O8 Zn1 N1 C6 5.2(2) . . . . ? O5 Zn1 N2 C14 91.8(2) 3_667 . . . ? N1 Zn1 N2 C14 -86.0(3) . . . . ? O1 Zn1 N2 C14 -170.5(2) . . . . ? O8 Zn1 N2 C14 -13.3(2) . . . . ? O5 Zn1 N2 C10 -99.2(2) 3_667 . . . ? N1 Zn1 N2 C10 83.0(2) . . . . ? O1 Zn1 N2 C10 -1.5(2) . . . . ? O8 Zn1 N2 C10 155.7(2) . . . . ? O4 Zn2 N4 C26 2.5(2) 3_667 . . . ? O7 Zn2 N4 C26 135.72(19) . . . . ? O6 Zn2 N4 C26 -105.8(2) 3_567 . . . ? O4 Zn2 N4 C22 -178.0(2) 3_667 . . . ? O7 Zn2 N4 C22 -44.7(2) . . . . ? O6 Zn2 N4 C22 73.7(2) 3_567 . . . ? Zn1 O1 C1 O2 171.5(2) . . . . ? Zn1 O1 C1 C2 -10.0(3) . . . . ? C6 N1 C2 C3 -0.3(4) . . . . ? Zn1 N1 C2 C3 -171.2(2) . . . . ? C6 N1 C2 C1 177.8(2) . . . . ? Zn1 N1 C2 C1 6.9(3) . . . . ? O2 C1 C2 N1 -179.0(2) . . . . ? O1 C1 C2 N1 2.3(4) . . . . ? O2 C1 C2 C3 -1.0(4) . . . . ? O1 C1 C2 C3 -179.6(3) . . . . ? N1 C2 C3 C4 -2.5(4) . . . . ? C1 C2 C3 C4 179.6(3) . . . . ? N1 C2 C3 C7 174.2(3) . . . . ? C1 C2 C3 C7 -3.7(4) . . . . ? C2 C3 C4 C5 3.4(4) . . . . ? C7 C3 C4 C5 -173.4(3) . . . . ? C3 C4 C5 C6 -1.6(4) . . . . ? C3 C4 C5 C8 176.1(3) . . . . ? C2 N1 C6 C5 2.3(4) . . . . ? Zn1 N1 C6 C5 172.5(2) . . . . ? C2 N1 C6 C9 -175.6(2) . . . . ? Zn1 N1 C6 C9 -5.3(3) . . . . ? C4 C5 C6 N1 -1.3(4) . . . . ? C8 C5 C6 N1 -178.7(3) . . . . ? C4 C5 C6 C9 176.2(3) . . . . ? C8 C5 C6 C9 -1.2(5) . . . . ? Zn2 O4 C7 O3 -163.6(2) 3_667 . . . ? Zn2 O4 C7 C3 22.2(4) 3_667 . . . ? C4 C3 C7 O3 -80.7(4) . . . . ? C2 C3 C7 O3 102.6(3) . . . . ? C4 C3 C7 O4 93.9(3) . . . . ? C2 C3 C7 O4 -82.8(4) . . . . ? Zn2 O6 C8 O5 -2.8(4) 3_567 . . . ? Zn2 O6 C8 C5 -176.49(18) 3_567 . . . ? Zn1 O5 C8 O6 162.7(2) 3_667 . . . ? Zn1 O5 C8 C5 -23.7(4) 3_667 . . . ? C6 C5 C8 O6 -89.1(4) . . . . ? C4 C5 C8 O6 93.4(3) . . . . ? C6 C5 C8 O5 96.9(4) . . . . ? C4 C5 C8 O5 -80.6(3) . . . . ? Zn1 O8 C9 O7 -174.8(2) . . . . ? Zn1 O8 C9 C6 2.7(3) . . . . ? Zn2 O7 C9 O8 -0.9(4) . . . . ? Zn2 O7 C9 C6 -178.42(18) . . . . ? N1 C6 C9 O8 1.2(4) . . . . ? C5 C6 C9 O8 -176.4(3) . . . . ? N1 C6 C9 O7 178.9(2) . . . . ? C5 C6 C9 O7 1.2(4) . . . . ? C14 N2 C10 C11 1.4(4) . . . . ? Zn1 N2 C10 C11 -168.1(2) . . . . ? N2 C10 C11 C12 1.9(5) . . . . ? C10 C11 C12 C13 -4.5(5) . . . . ? C10 C11 C12 C15 173.7(3) . . . . ? C11 C12 C13 C14 4.0(5) . . . . ? C15 C12 C13 C14 -174.3(3) . . . . ? C10 N2 C14 C13 -1.9(5) . . . . ? Zn1 N2 C14 C13 167.3(3) . . . . ? C12 C13 C14 N2 -0.8(5) . . . . ? C11 C12 C15 C16 -5.3(5) . . . . ? C13 C12 C15 C16 172.9(3) . . . . ? C12 C15 C16 C17 -179.8(3) . . . . ? C15 C16 C17 C18 -163.4(3) . . . . ? C15 C16 C17 C21 15.8(5) . . . . ? C21 C17 C18 C19 -2.8(5) . . . . ? C16 C17 C18 C19 176.5(3) . . . . ? C20 N3 C19 C18 0.5(5) . . . . ? C17 C18 C19 N3 1.5(5) . . . . ? C19 N3 C20 C21 -1.3(5) . . . . ? N3 C20 C21 C17 -0.1(6) . . . . ? C18 C17 C21 C20 2.1(5) . . . . ? C16 C17 C21 C20 -177.1(3) . . . . ? C26 N4 C22 C23 1.1(4) . . . . ? Zn2 N4 C22 C23 -178.5(2) . . . . ? N4 C22 C23 C24 1.0(4) . . . . ? C22 C23 C24 C25 -2.1(4) . . . . ? C22 C23 C24 C27 176.7(2) . . . . ? C23 C24 C25 C26 1.3(4) . . . . ? C27 C24 C25 C26 -177.6(2) . . . . ? C22 N4 C26 C25 -2.0(4) . . . . ? Zn2 N4 C26 C25 177.6(2) . . . . ? C24 C25 C26 N4 0.8(4) . . . . ? C25 C24 C27 C27 178.2(3) . . . 3_557 ? C23 C24 C27 C27 -0.6(5) . . . 3_557 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.619 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 972279' ####################################################################### # # 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_shelx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N4 O9 Zn' _chemical_formula_weight 519.72 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' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.526(3) _cell_length_b 11.277(3) _cell_length_c 12.205(3) _cell_angle_alpha 71.997(14) _cell_angle_beta 87.887(18) _cell_angle_gamma 74.766(14) _cell_volume 949.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3448 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.818 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 1.363 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7722 _exptl_absorpt_correction_T_max 0.8535 _exptl_absorpt_process_details CRYSALISPRO _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12267 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.93 _reflns_number_total 4508 _reflns_number_gt 3483 _reflns_threshold_expression >2sigma(I) _computing_data_collection CRYSALISPRO _computing_cell_refinement CRYSALISPRO _computing_data_reduction CRYSALISPRO _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^)+(0.0389P)^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 4508 _refine_ls_number_parameters 320 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.46410(4) 0.25113(3) 0.09766(2) 0.01565(9) Uani 1 1 d . . . O1 O 0.6064(2) 0.06441(15) 0.18775(13) 0.0165(4) Uani 1 1 d . . . O2 O 0.7643(2) -0.12470(15) 0.16401(13) 0.0186(4) Uani 1 1 d . . . O3 O 1.0374(2) -0.15213(15) -0.04705(14) 0.0212(4) Uani 1 1 d . . . O4 O 0.7929(2) -0.22281(14) -0.06355(13) 0.0162(3) Uani 1 1 d . . . O5 O 0.6185(2) 0.17458(16) -0.42035(14) 0.0231(4) Uani 1 1 d . . . O6 O 0.4771(3) 0.36384(16) -0.40262(14) 0.0288(5) Uani 1 1 d . . . H6 H 0.4372 0.3939 -0.3489 0.043 Uiso 1 1 calc R . . O7 O 0.3628(2) 0.46358(15) -0.25848(13) 0.0219(4) Uani 1 1 d . . . O8 O 0.3920(2) 0.41628(14) -0.06921(13) 0.0173(4) Uani 1 1 d . . . O9 O 0.7001(2) 0.31190(16) 0.12381(14) 0.0181(4) Uani 1 1 d D . . N1 N 0.5766(2) 0.18035(17) -0.03599(15) 0.0125(4) Uani 1 1 d . . . N2 N 0.7142(3) 0.06612(18) -0.19774(15) 0.0142(4) Uani 1 1 d . . . N3 N 0.3176(3) 0.36678(18) 0.18957(16) 0.0162(4) Uani 1 1 d . . . N4 N -0.1699(3) 0.9363(2) 0.60461(18) 0.0221(5) Uani 1 1 d D . . C1 C 0.6862(3) -0.0082(2) 0.12848(19) 0.0140(5) Uani 1 1 d . . . C2 C 0.6731(3) 0.0581(2) -0.00249(19) 0.0123(5) Uani 1 1 d . . . C3 C 0.7479(3) 0.0003(2) -0.08619(19) 0.0125(5) Uani 1 1 d . . . C4 C 0.8690(3) -0.1382(2) -0.06091(18) 0.0144(5) Uani 1 1 d . . . C5 C 0.5662(3) 0.2439(2) -0.3599(2) 0.0184(5) Uani 1 1 d . . . C6 C 0.6078(3) 0.1886(2) -0.23005(19) 0.0140(5) Uani 1 1 d . . . C7 C 0.5410(3) 0.2495(2) -0.14707(19) 0.0128(5) Uani 1 1 d . . . C8 C 0.4227(3) 0.3872(2) -0.1594(2) 0.0149(5) Uani 1 1 d . . . C9 C 0.1732(3) 0.4661(2) 0.1371(2) 0.0173(5) Uani 1 1 d . . . H9 H 0.1337 0.4743 0.0614 0.021 Uiso 1 1 calc R . . C10 C 0.0800(3) 0.5563(2) 0.18823(19) 0.0175(5) Uani 1 1 d . . . H10 H -0.0200 0.6258 0.1477 0.021 Uiso 1 1 calc R . . C11 C 0.1339(3) 0.5446(2) 0.2997(2) 0.0183(5) Uani 1 1 d . . . C12 C 0.2796(3) 0.4394(2) 0.3550(2) 0.0195(5) Uani 1 1 d . . . H12 H 0.3173 0.4257 0.4324 0.023 Uiso 1 1 calc R . . C13 C 0.3685(3) 0.3556(2) 0.2970(2) 0.0184(5) Uani 1 1 d . . . H13 H 0.4708 0.2865 0.3349 0.022 Uiso 1 1 calc R . . C14 C 0.0403(3) 0.6454(2) 0.3514(2) 0.0218(6) Uani 1 1 d . . . H14 H -0.0572 0.7141 0.3070 0.026 Uiso 1 1 calc R . . C15 C 0.0829(3) 0.6472(2) 0.4565(2) 0.0203(5) Uani 1 1 d . . . H15 H 0.1782 0.5777 0.5020 0.024 Uiso 1 1 calc R . . C16 C -0.0081(3) 0.7494(2) 0.5053(2) 0.0189(5) Uani 1 1 d . . . C17 C -0.1515(3) 0.8551(2) 0.4471(2) 0.0217(5) Uani 1 1 d . . . H17 H -0.1945 0.8630 0.3722 0.026 Uiso 1 1 calc R . . C18 C -0.2295(3) 0.9469(2) 0.4981(2) 0.0238(6) Uani 1 1 d . . . H18 H -0.3268 1.0190 0.4584 0.029 Uiso 1 1 calc R . . C19 C -0.0314(3) 0.8373(2) 0.6624(2) 0.0210(5) Uani 1 1 d . . . H19 H 0.0092 0.8329 0.7367 0.025 Uiso 1 1 calc R . . C20 C 0.0527(3) 0.7422(2) 0.61546(19) 0.0189(5) Uani 1 1 d . . . H20 H 0.1511 0.6720 0.6568 0.023 Uiso 1 1 calc R . . H4 H -0.229(4) 1.001(2) 0.632(2) 0.050(10) Uiso 1 1 d D . . H9A H 0.682(3) 0.3930(10) 0.105(2) 0.025(8) Uiso 1 1 d D . . H9B H 0.791(3) 0.272(2) 0.094(2) 0.055(11) Uiso 1 1 d 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 0.01731(16) 0.01290(15) 0.01663(15) -0.00816(11) -0.00047(11) 0.00063(11) O1 0.0190(9) 0.0153(8) 0.0148(8) -0.0077(7) 0.0014(7) -0.0005(7) O2 0.0232(9) 0.0127(8) 0.0175(9) -0.0052(7) -0.0032(7) 0.0004(7) O3 0.0133(9) 0.0164(9) 0.0341(10) -0.0119(8) -0.0015(7) 0.0008(7) O4 0.0159(9) 0.0127(8) 0.0217(9) -0.0089(7) -0.0008(7) -0.0023(7) O5 0.0329(11) 0.0179(9) 0.0176(9) -0.0106(7) -0.0009(8) 0.0011(8) O6 0.0446(12) 0.0191(9) 0.0149(9) -0.0074(8) -0.0047(8) 0.0083(8) O7 0.0288(10) 0.0126(8) 0.0179(9) -0.0041(7) -0.0027(7) 0.0049(7) O8 0.0219(9) 0.0119(8) 0.0167(8) -0.0068(7) 0.0010(7) 0.0007(7) O9 0.0173(9) 0.0121(9) 0.0249(9) -0.0093(8) -0.0007(7) 0.0006(7) N1 0.0118(10) 0.0113(9) 0.0150(10) -0.0060(8) -0.0002(8) -0.0019(8) N2 0.0151(10) 0.0115(9) 0.0153(10) -0.0044(8) 0.0002(8) -0.0022(8) N3 0.0174(10) 0.0155(10) 0.0170(10) -0.0090(8) -0.0004(8) -0.0014(8) N4 0.0226(12) 0.0167(11) 0.0267(12) -0.0111(9) 0.0019(9) 0.0006(9) C1 0.0132(12) 0.0134(11) 0.0157(11) -0.0052(9) -0.0020(9) -0.0029(9) C2 0.0097(11) 0.0115(11) 0.0173(12) -0.0067(9) -0.0004(9) -0.0024(9) C3 0.0100(11) 0.0115(11) 0.0170(11) -0.0058(9) -0.0001(9) -0.0026(9) C4 0.0191(13) 0.0122(11) 0.0095(11) -0.0042(9) 0.0009(9) 0.0009(9) C5 0.0200(13) 0.0175(12) 0.0166(12) -0.0062(10) -0.0003(10) -0.0020(10) C6 0.0147(12) 0.0108(11) 0.0170(12) -0.0057(9) 0.0002(9) -0.0024(9) C7 0.0105(11) 0.0136(11) 0.0158(11) -0.0063(9) -0.0001(9) -0.0032(9) C8 0.0123(12) 0.0116(11) 0.0215(12) -0.0065(10) 0.0017(10) -0.0029(9) C9 0.0180(13) 0.0196(12) 0.0143(12) -0.0080(10) -0.0001(9) -0.0018(10) C10 0.0159(12) 0.0163(12) 0.0180(12) -0.0062(10) -0.0023(10) 0.0011(10) C11 0.0168(12) 0.0204(13) 0.0189(12) -0.0088(10) 0.0011(10) -0.0039(10) C12 0.0228(14) 0.0219(13) 0.0138(12) -0.0078(10) -0.0019(10) -0.0025(11) C13 0.0190(13) 0.0165(12) 0.0187(12) -0.0063(10) -0.0017(10) -0.0016(10) C14 0.0232(14) 0.0184(13) 0.0216(13) -0.0094(11) -0.0023(10) 0.0022(10) C15 0.0200(13) 0.0176(12) 0.0216(13) -0.0093(11) 0.0004(10) 0.0020(10) C16 0.0186(13) 0.0217(13) 0.0184(12) -0.0100(10) 0.0057(10) -0.0048(10) C17 0.0226(14) 0.0235(13) 0.0177(12) -0.0060(11) -0.0015(10) -0.0043(11) C18 0.0221(14) 0.0183(13) 0.0260(14) -0.0039(11) -0.0028(11) -0.0001(11) C19 0.0247(14) 0.0206(13) 0.0183(12) -0.0090(10) 0.0007(10) -0.0034(11) C20 0.0207(13) 0.0170(12) 0.0172(12) -0.0076(10) 0.0007(10) 0.0009(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 Zn1 N3 2.0572(19) . ? Zn1 O1 2.0640(17) . ? Zn1 N1 2.0886(18) . ? Zn1 O4 2.1172(17) 2_655 ? Zn1 O9 2.1313(18) . ? Zn1 O8 2.2619(16) . ? O1 C1 1.277(3) . ? O2 C1 1.233(3) . ? O3 C4 1.246(3) . ? O4 C4 1.243(3) . ? O4 Zn1 2.1172(17) 2_655 ? O5 C5 1.218(3) . ? O6 C5 1.290(3) . ? O6 H6 0.8400 . ? O7 C8 1.265(3) . ? O8 C8 1.240(3) . ? O9 H9A 0.845(9) . ? O9 H9B 0.851(9) . ? N1 C2 1.320(3) . ? N1 C7 1.335(3) . ? N2 C3 1.331(3) . ? N2 C6 1.345(3) . ? N3 C13 1.339(3) . ? N3 C9 1.347(3) . ? N4 C19 1.337(3) . ? N4 C18 1.351(3) . ? N4 H4 0.900(10) . ? C1 C2 1.535(3) . ? C2 C3 1.400(3) . ? C3 C4 1.530(3) . ? C5 C6 1.524(3) . ? C6 C7 1.400(3) . ? C7 C8 1.538(3) . ? C9 C10 1.379(3) . ? C9 H9 0.9500 . ? C10 C11 1.391(3) . ? C10 H10 0.9500 . ? C11 C12 1.394(3) . ? C11 C14 1.476(3) . ? C12 C13 1.374(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.341(3) . ? C14 H14 0.9500 . ? C15 C16 1.459(3) . ? C15 H15 0.9500 . ? C16 C17 1.396(3) . ? C16 C20 1.408(3) . ? C17 C18 1.363(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.370(3) . ? C19 H19 0.9500 . ? C20 H20 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 N3 Zn1 O1 118.15(7) . . ? N3 Zn1 N1 163.31(7) . . ? O1 Zn1 N1 78.48(7) . . ? N3 Zn1 O4 85.57(7) . 2_655 ? O1 Zn1 O4 100.66(6) . 2_655 ? N1 Zn1 O4 90.02(7) . 2_655 ? N3 Zn1 O9 88.29(7) . . ? O1 Zn1 O9 88.31(7) . . ? N1 Zn1 O9 93.93(7) . . ? O4 Zn1 O9 170.77(6) 2_655 . ? N3 Zn1 O8 91.21(7) . . ? O1 Zn1 O8 150.46(6) . . ? N1 Zn1 O8 72.30(7) . . ? O4 Zn1 O8 83.81(6) 2_655 . ? O9 Zn1 O8 89.44(6) . . ? C1 O1 Zn1 117.03(14) . . ? C4 O4 Zn1 142.75(15) . 2_655 ? C5 O6 H6 109.5 . . ? C8 O8 Zn1 116.29(14) . . ? Zn1 O9 H9A 114.4(17) . . ? Zn1 O9 H9B 108(2) . . ? H9A O9 H9B 115.8(16) . . ? C2 N1 C7 122.32(19) . . ? C2 N1 Zn1 114.71(14) . . ? C7 N1 Zn1 122.73(15) . . ? C3 N2 C6 119.77(19) . . ? C13 N3 C9 117.5(2) . . ? C13 N3 Zn1 122.99(16) . . ? C9 N3 Zn1 119.27(15) . . ? C19 N4 C18 121.4(2) . . ? C19 N4 H4 124(2) . . ? C18 N4 H4 115(2) . . ? O2 C1 O1 127.5(2) . . ? O2 C1 C2 117.39(19) . . ? O1 C1 C2 115.00(19) . . ? N1 C2 C3 119.0(2) . . ? N1 C2 C1 114.68(19) . . ? C3 C2 C1 126.3(2) . . ? N2 C3 C2 120.3(2) . . ? N2 C3 C4 114.65(19) . . ? C2 C3 C4 125.1(2) . . ? O4 C4 O3 126.8(2) . . ? O4 C4 C3 117.6(2) . . ? O3 C4 C3 115.4(2) . . ? O5 C5 O6 121.9(2) . . ? O5 C5 C6 119.5(2) . . ? O6 C5 C6 118.6(2) . . ? N2 C6 C7 120.3(2) . . ? N2 C6 C5 112.67(19) . . ? C7 C6 C5 126.9(2) . . ? N1 C7 C6 118.2(2) . . ? N1 C7 C8 110.53(19) . . ? C6 C7 C8 131.2(2) . . ? O8 C8 O7 123.8(2) . . ? O8 C8 C7 116.7(2) . . ? O7 C8 C7 119.5(2) . . ? N3 C9 C10 123.0(2) . . ? N3 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C9 C10 C11 119.3(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C11 C12 117.5(2) . . ? C10 C11 C14 119.0(2) . . ? C12 C11 C14 123.5(2) . . ? C13 C12 C11 119.6(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? N3 C13 C12 123.1(2) . . ? N3 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? C15 C14 C11 124.7(2) . . ? C15 C14 H14 117.6 . . ? C11 C14 H14 117.6 . . ? C14 C15 C16 124.0(2) . . ? C14 C15 H15 118.0 . . ? C16 C15 H15 118.0 . . ? C17 C16 C20 118.3(2) . . ? C17 C16 C15 123.0(2) . . ? C20 C16 C15 118.7(2) . . ? C18 C17 C16 119.6(2) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? N4 C18 C17 120.7(2) . . ? N4 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? N4 C19 C20 120.6(2) . . ? N4 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C16 119.4(2) . . ? C19 C20 H20 120.3 . . ? C16 C20 H20 120.3 . . ? 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 N3 Zn1 O1 C1 175.50(15) . . . . ? N1 Zn1 O1 C1 -2.99(16) . . . . ? O4 Zn1 O1 C1 84.84(16) 2_655 . . . ? O9 Zn1 O1 C1 -97.35(16) . . . . ? O8 Zn1 O1 C1 -11.5(2) . . . . ? N3 Zn1 O8 C8 -166.44(17) . . . . ? O1 Zn1 O8 C8 19.7(2) . . . . ? N1 Zn1 O8 C8 10.98(16) . . . . ? O4 Zn1 O8 C8 -81.03(17) 2_655 . . . ? O9 Zn1 O8 C8 105.29(17) . . . . ? N3 Zn1 N1 C2 -173.5(2) . . . . ? O1 Zn1 N1 C2 1.89(15) . . . . ? O4 Zn1 N1 C2 -98.99(16) 2_655 . . . ? O9 Zn1 N1 C2 89.35(16) . . . . ? O8 Zn1 N1 C2 177.51(17) . . . . ? N3 Zn1 N1 C7 1.0(4) . . . . ? O1 Zn1 N1 C7 176.38(18) . . . . ? O4 Zn1 N1 C7 75.49(18) 2_655 . . . ? O9 Zn1 N1 C7 -96.16(18) . . . . ? O8 Zn1 N1 C7 -8.00(17) . . . . ? O1 Zn1 N3 C13 31.0(2) . . . . ? N1 Zn1 N3 C13 -154.2(2) . . . . ? O4 Zn1 N3 C13 130.72(19) 2_655 . . . ? O9 Zn1 N3 C13 -56.18(19) . . . . ? O8 Zn1 N3 C13 -145.59(19) . . . . ? O1 Zn1 N3 C9 -155.16(16) . . . . ? N1 Zn1 N3 C9 19.7(4) . . . . ? O4 Zn1 N3 C9 -55.43(18) 2_655 . . . ? O9 Zn1 N3 C9 117.68(18) . . . . ? O8 Zn1 N3 C9 28.27(18) . . . . ? Zn1 O1 C1 O2 -173.25(19) . . . . ? Zn1 O1 C1 C2 3.4(2) . . . . ? C7 N1 C2 C3 3.0(3) . . . . ? Zn1 N1 C2 C3 177.49(16) . . . . ? C7 N1 C2 C1 -175.28(19) . . . . ? Zn1 N1 C2 C1 -0.8(2) . . . . ? O2 C1 C2 N1 175.3(2) . . . . ? O1 C1 C2 N1 -1.7(3) . . . . ? O2 C1 C2 C3 -2.8(3) . . . . ? O1 C1 C2 C3 -179.8(2) . . . . ? C6 N2 C3 C2 0.0(3) . . . . ? C6 N2 C3 C4 179.42(19) . . . . ? N1 C2 C3 N2 -3.3(3) . . . . ? C1 C2 C3 N2 174.7(2) . . . . ? N1 C2 C3 C4 177.4(2) . . . . ? C1 C2 C3 C4 -4.6(4) . . . . ? Zn1 O4 C4 O3 -172.17(16) 2_655 . . . ? Zn1 O4 C4 C3 2.8(3) 2_655 . . . ? N2 C3 C4 O4 -82.4(3) . . . . ? C2 C3 C4 O4 97.0(3) . . . . ? N2 C3 C4 O3 93.1(2) . . . . ? C2 C3 C4 O3 -87.5(3) . . . . ? C3 N2 C6 C7 3.5(3) . . . . ? C3 N2 C6 C5 -173.55(19) . . . . ? O5 C5 C6 N2 4.7(3) . . . . ? O6 C5 C6 N2 -174.8(2) . . . . ? O5 C5 C6 C7 -172.2(2) . . . . ? O6 C5 C6 C7 8.3(4) . . . . ? C2 N1 C7 C6 0.5(3) . . . . ? Zn1 N1 C7 C6 -173.56(15) . . . . ? C2 N1 C7 C8 178.73(19) . . . . ? Zn1 N1 C7 C8 4.7(3) . . . . ? N2 C6 C7 N1 -3.9(3) . . . . ? C5 C6 C7 N1 172.8(2) . . . . ? N2 C6 C7 C8 178.4(2) . . . . ? C5 C6 C7 C8 -5.0(4) . . . . ? Zn1 O8 C8 O7 167.80(17) . . . . ? Zn1 O8 C8 C7 -12.3(3) . . . . ? N1 C7 C8 O8 5.7(3) . . . . ? C6 C7 C8 O8 -176.4(2) . . . . ? N1 C7 C8 O7 -174.4(2) . . . . ? C6 C7 C8 O7 3.5(4) . . . . ? C13 N3 C9 C10 1.3(4) . . . . ? Zn1 N3 C9 C10 -172.88(18) . . . . ? N3 C9 C10 C11 -1.1(4) . . . . ? C9 C10 C11 C12 -1.0(4) . . . . ? C9 C10 C11 C14 176.7(2) . . . . ? C10 C11 C12 C13 2.7(4) . . . . ? C14 C11 C12 C13 -174.8(2) . . . . ? C9 N3 C13 C12 0.5(4) . . . . ? Zn1 N3 C13 C12 174.50(18) . . . . ? C11 C12 C13 N3 -2.6(4) . . . . ? C10 C11 C14 C15 -178.0(2) . . . . ? C12 C11 C14 C15 -0.5(4) . . . . ? C11 C14 C15 C16 178.4(2) . . . . ? C14 C15 C16 C17 0.9(4) . . . . ? C14 C15 C16 C20 -178.2(2) . . . . ? C20 C16 C17 C18 -0.7(4) . . . . ? C15 C16 C17 C18 -179.8(2) . . . . ? C19 N4 C18 C17 1.1(4) . . . . ? C16 C17 C18 N4 -0.2(4) . . . . ? C18 N4 C19 C20 -1.0(4) . . . . ? N4 C19 C20 C16 0.0(4) . . . . ? C17 C16 C20 C19 0.8(4) . . . . ? C15 C16 C20 C19 180.0(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 N4 H4 O5 0.900(10) 1.92(2) 2.670(3) 140(3) 1_466 N4 H4 N2 0.900(10) 2.396(19) 3.175(3) 145(2) 1_466 O9 H9A O8 0.845(9) 1.984(10) 2.824(2) 172(2) 2_665 O9 H9B O3 0.851(9) 1.826(10) 2.658(2) 166(2) 2_755 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.690 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 972280' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 N3 O8.50 Zn' _chemical_formula_weight 456.73 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4083(15) _cell_length_b 10.890(2) _cell_length_c 13.632(3) _cell_angle_alpha 66.67(3) _cell_angle_beta 78.17(3) _cell_angle_gamma 71.78(3) _cell_volume 955.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3178 _cell_measurement_theta_min 2.1077 _cell_measurement_theta_max 27.8485 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 1.339 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7756 _exptl_absorpt_correction_T_max 0.8559 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9423 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0684 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.86 _reflns_number_total 4441 _reflns_number_gt 3168 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0622P)^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 4441 _refine_ls_number_parameters 298 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.043 _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 1.0000 0.5000 0.0000 0.00757(12) Uani 1 2 d S . . Zn2 Zn 0.5000 1.0000 0.0000 0.00737(12) Uani 1 2 d S . . O1 O 0.8596(3) 0.18140(19) 0.02686(16) 0.0164(4) Uani 1 1 d . . . O2 O 0.7360(3) 0.1764(2) 0.19354(15) 0.0193(4) Uani 1 1 d . . . O3 O 0.8351(3) 0.70163(18) -0.04172(14) 0.0118(4) Uani 1 1 d . . . O4 O 0.5402(3) 0.84233(17) -0.06264(14) 0.0101(4) Uani 1 1 d . . . O5 O 0.7862(3) 0.9770(3) -0.0066(3) 0.0439(8) Uani 1 1 d D . . H5A H 0.867(4) 0.906(2) -0.012(3) 0.053 Uiso 1 1 d D . . H5B H 0.817(5) 1.031(3) 0.014(3) 0.053 Uiso 1 1 d D . . N1 N 0.6891(3) 0.4792(2) 0.01587(16) 0.0076(4) Uani 1 1 d . . . N2 N 0.9756(3) 0.4866(2) 0.16161(17) 0.0136(5) Uani 1 1 d . . . N3 N 0.5009(4) 0.8536(2) 0.16128(18) 0.0203(6) Uani 1 1 d . . . C1 C 0.7467(4) 0.2282(3) 0.0939(2) 0.0134(5) Uani 1 1 d . . . C2 C 0.6139(4) 0.3709(3) 0.04385(19) 0.0083(5) Uani 1 1 d . . . C3 C 0.5764(4) 0.6071(3) -0.02663(19) 0.0079(5) Uani 1 1 d . . . C4 C 0.6593(4) 0.7276(3) -0.04713(19) 0.0082(5) Uani 1 1 d . . . C5 C 0.9636(5) 0.3706(3) 0.2448(2) 0.0212(7) Uani 1 1 d . . . H5 H 0.9541 0.2938 0.2313 0.025 Uiso 1 1 calc R . . C6 C 0.9643(5) 0.3578(4) 0.3502(2) 0.0289(8) Uani 1 1 d . . . H6 H 0.9526 0.2739 0.4070 0.035 Uiso 1 1 calc R . . C7 C 0.9821(5) 0.4674(4) 0.3733(2) 0.0265(8) Uani 1 1 d . . . C8 C 0.9908(5) 0.5907(3) 0.2851(2) 0.0231(7) Uani 1 1 d . . . H8 H 0.9995 0.6696 0.2959 0.028 Uiso 1 1 calc R . . C9 C 0.9866(4) 0.5949(3) 0.1830(2) 0.0169(6) Uani 1 1 d . . . H9 H 0.9918 0.6787 0.1245 0.020 Uiso 1 1 calc R . . C10 C 0.9894(6) 0.4526(4) 0.4840(2) 0.0348(9) Uani 1 1 d . . . H10 H 0.9778 0.3669 0.5383 0.042 Uiso 1 1 calc R . . C11 C 0.4409(5) 0.7384(3) 0.1892(2) 0.0252(7) Uani 1 1 d . . . H11 H 0.3957 0.7236 0.1355 0.030 Uiso 1 1 calc R . . C12 C 0.4416(5) 0.6404(3) 0.2921(2) 0.0292(8) Uani 1 1 d . . . H12 H 0.4012 0.5595 0.3075 0.035 Uiso 1 1 calc R . . C13 C 0.5026(5) 0.6620(3) 0.3732(2) 0.0266(7) Uani 1 1 d . . . C14 C 0.5600(5) 0.7837(3) 0.3442(2) 0.0270(8) Uani 1 1 d . . . H14 H 0.5990 0.8040 0.3971 0.032 Uiso 1 1 calc R . . C15 C 0.5600(5) 0.8747(3) 0.2387(2) 0.0231(7) Uani 1 1 d . . . H15 H 0.6035 0.9550 0.2204 0.028 Uiso 1 1 calc R . . C16 C 0.5072(6) 0.5656(3) 0.4839(2) 0.0312(8) Uani 1 1 d . . . H16 H 0.5214 0.5971 0.5370 0.037 Uiso 1 1 calc R . . O6 O 0.2063(8) -0.0069(6) 0.4455(4) 0.0406(12) Uani 0.50 1 d PU A 1 O7 O -0.0397(8) -0.0684(5) 0.3433(4) 0.0406(13) Uani 0.50 1 d PU B 1 O8 O 0.3224(8) 0.0323(6) 0.4904(4) 0.0481(14) Uani 0.50 1 d PU C 2 O9 O 0.1059(8) -0.0902(6) 0.4357(4) 0.0431(13) Uani 0.50 1 d PU D 2 O10 O 0.0232(7) -0.0783(5) 0.2474(3) 0.0301(10) Uani 0.50 1 d PU E 2 O11 O 0.4399(9) 0.1872(7) 0.3741(5) 0.0533(15) Uani 0.50 1 d PU F 3 O11' O 0.5577(9) 0.2070(6) 0.3888(4) 0.0427(13) Uani 0.50 1 d PU G 4 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 0.0069(2) 0.0075(2) 0.0082(2) -0.00393(16) -0.00169(15) 0.00052(16) Zn2 0.0071(2) 0.0046(2) 0.0098(2) -0.00188(16) -0.00083(15) -0.00167(16) O1 0.0069(9) 0.0118(9) 0.0340(12) -0.0140(9) 0.0013(8) -0.0017(7) O2 0.0259(12) 0.0127(10) 0.0170(10) 0.0006(8) -0.0113(8) -0.0038(9) O3 0.0080(9) 0.0081(9) 0.0196(10) -0.0052(8) -0.0029(7) -0.0012(7) O4 0.0102(9) 0.0062(8) 0.0141(9) -0.0040(7) -0.0028(7) -0.0008(7) O5 0.0067(11) 0.0412(16) 0.113(2) -0.0628(17) -0.0022(13) -0.0013(11) N1 0.0066(11) 0.0060(10) 0.0107(10) -0.0035(8) -0.0012(8) -0.0013(8) N2 0.0148(12) 0.0190(12) 0.0108(11) -0.0071(9) -0.0012(9) -0.0070(10) N3 0.0387(17) 0.0113(11) 0.0095(11) -0.0022(9) -0.0019(10) -0.0067(11) C1 0.0075(13) 0.0096(12) 0.0250(15) -0.0065(11) -0.0052(10) -0.0020(10) C2 0.0095(12) 0.0058(11) 0.0077(11) -0.0025(9) -0.0008(9) 0.0005(9) C3 0.0085(12) 0.0066(11) 0.0092(12) -0.0038(10) 0.0002(9) -0.0020(9) C4 0.0101(13) 0.0073(12) 0.0062(11) -0.0017(9) -0.0014(9) -0.0014(10) C5 0.0318(18) 0.0280(17) 0.0126(14) -0.0079(13) -0.0002(12) -0.0197(14) C6 0.049(2) 0.0351(19) 0.0127(14) -0.0055(14) 0.0011(14) -0.0313(18) C7 0.042(2) 0.0385(19) 0.0120(14) -0.0102(13) 0.0046(13) -0.0313(17) C8 0.0324(18) 0.0328(18) 0.0170(14) -0.0157(13) 0.0063(12) -0.0225(15) C9 0.0191(15) 0.0208(15) 0.0158(14) -0.0090(12) 0.0025(11) -0.0109(12) C10 0.059(3) 0.051(2) 0.0121(15) -0.0108(15) 0.0059(15) -0.044(2) C11 0.049(2) 0.0115(14) 0.0149(14) -0.0041(12) 0.0049(13) -0.0124(14) C12 0.054(2) 0.0118(15) 0.0163(15) -0.0029(12) 0.0089(14) -0.0112(15) C13 0.045(2) 0.0134(14) 0.0121(14) -0.0028(12) 0.0046(13) -0.0015(14) C14 0.051(2) 0.0105(14) 0.0144(14) -0.0041(12) -0.0028(14) -0.0012(14) C15 0.040(2) 0.0110(14) 0.0169(15) -0.0038(12) -0.0067(13) -0.0044(13) C16 0.052(2) 0.0161(15) 0.0124(14) -0.0026(12) 0.0068(14) -0.0013(15) O6 0.038(3) 0.046(3) 0.028(2) -0.014(2) 0.003(2) 0.000(2) O7 0.047(3) 0.025(3) 0.036(3) 0.002(2) -0.004(2) -0.007(2) O8 0.034(3) 0.063(4) 0.041(3) -0.013(3) 0.003(2) -0.014(3) O9 0.042(3) 0.045(3) 0.036(3) -0.008(2) 0.001(2) -0.012(3) O10 0.027(3) 0.024(2) 0.026(2) -0.0009(19) -0.0001(19) -0.002(2) O11 0.040(4) 0.070(4) 0.046(3) -0.026(3) 0.003(3) -0.007(3) O11' 0.040(3) 0.058(3) 0.040(3) -0.032(3) 0.004(2) -0.012(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 Zn1 O3 2.0629(19) . ? Zn1 O3 2.0629(19) 2_765 ? Zn1 N2 2.123(2) 2_765 ? Zn1 N2 2.123(2) . ? Zn1 N1 2.342(2) 2_765 ? Zn1 N1 2.342(2) . ? Zn2 O5 2.043(2) 2_675 ? Zn2 O5 2.043(2) . ? Zn2 O4 2.1220(17) . ? Zn2 O4 2.1220(17) 2_675 ? Zn2 N3 2.144(2) . ? Zn2 N3 2.144(2) 2_675 ? O1 C1 1.258(3) . ? O2 C1 1.244(3) . ? O3 C4 1.255(3) . ? O4 C4 1.250(3) . ? O5 H5A 0.838(10) . ? O5 H5B 0.836(10) . ? N1 C3 1.343(3) . ? N1 C2 1.348(3) . ? N2 C5 1.336(4) . ? N2 C9 1.351(3) . ? N3 C15 1.342(4) . ? N3 C11 1.348(3) . ? C1 C2 1.526(4) . ? C2 C3 1.407(4) 2_665 ? C3 C2 1.407(4) 2_665 ? C3 C4 1.523(3) . ? C5 C6 1.388(4) . ? C5 H5 0.9500 . ? C6 C7 1.398(4) . ? C6 H6 0.9500 . ? C7 C8 1.413(4) . ? C7 C10 1.464(4) . ? C8 C9 1.381(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C10 1.330(6) 2_766 ? C10 H10 0.9500 . ? C11 C12 1.386(4) . ? C11 H11 0.9500 . ? C12 C13 1.399(5) . ? C12 H12 0.9500 . ? C13 C14 1.401(4) . ? C13 C16 1.457(4) . ? C14 C15 1.387(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C16 1.350(6) 2_666 ? C16 H16 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 O3 Zn1 O3 180.000(1) . 2_765 ? O3 Zn1 N2 89.95(9) . 2_765 ? O3 Zn1 N2 90.05(9) 2_765 2_765 ? O3 Zn1 N2 90.05(9) . . ? O3 Zn1 N2 89.95(9) 2_765 . ? N2 Zn1 N2 180.0 2_765 . ? O3 Zn1 N1 103.80(7) . 2_765 ? O3 Zn1 N1 76.20(7) 2_765 2_765 ? N2 Zn1 N1 92.47(8) 2_765 2_765 ? N2 Zn1 N1 87.53(8) . 2_765 ? O3 Zn1 N1 76.20(7) . . ? O3 Zn1 N1 103.80(7) 2_765 . ? N2 Zn1 N1 87.53(8) 2_765 . ? N2 Zn1 N1 92.47(8) . . ? N1 Zn1 N1 180.0 2_765 . ? O5 Zn2 O5 180.0 2_675 . ? O5 Zn2 O4 86.64(8) 2_675 . ? O5 Zn2 O4 93.36(8) . . ? O5 Zn2 O4 93.36(8) 2_675 2_675 ? O5 Zn2 O4 86.64(8) . 2_675 ? O4 Zn2 O4 180.0 . 2_675 ? O5 Zn2 N3 89.38(13) 2_675 . ? O5 Zn2 N3 90.63(13) . . ? O4 Zn2 N3 91.42(8) . . ? O4 Zn2 N3 88.58(8) 2_675 . ? O5 Zn2 N3 90.63(13) 2_675 2_675 ? O5 Zn2 N3 89.37(13) . 2_675 ? O4 Zn2 N3 88.58(8) . 2_675 ? O4 Zn2 N3 91.42(8) 2_675 2_675 ? N3 Zn2 N3 180.0 . 2_675 ? C4 O3 Zn1 119.99(15) . . ? C4 O4 Zn2 132.01(16) . . ? Zn2 O5 H5A 122(2) . . ? Zn2 O5 H5B 116(2) . . ? H5A O5 H5B 120(2) . . ? C3 N1 C2 118.1(2) . . ? C3 N1 Zn1 107.51(15) . . ? C2 N1 Zn1 133.72(17) . . ? C5 N2 C9 117.5(2) . . ? C5 N2 Zn1 122.53(18) . . ? C9 N2 Zn1 119.74(18) . . ? C15 N3 C11 117.5(2) . . ? C15 N3 Zn2 120.73(19) . . ? C11 N3 Zn2 121.7(2) . . ? O2 C1 O1 128.7(3) . . ? O2 C1 C2 117.1(2) . . ? O1 C1 C2 114.1(2) . . ? N1 C2 C3 120.2(2) . 2_665 ? N1 C2 C1 115.9(2) . . ? C3 C2 C1 123.9(2) 2_665 . ? N1 C3 C2 121.7(2) . 2_665 ? N1 C3 C4 116.7(2) . . ? C2 C3 C4 121.4(2) 2_665 . ? O4 C4 O3 126.8(2) . . ? O4 C4 C3 115.2(2) . . ? O3 C4 C3 117.9(2) . . ? N2 C5 C6 122.7(3) . . ? N2 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C5 C6 C7 120.4(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C8 116.6(3) . . ? C6 C7 C10 120.6(3) . . ? C8 C7 C10 122.8(3) . . ? C9 C8 C7 119.1(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? N2 C9 C8 123.7(3) . . ? N2 C9 H9 118.2 . . ? C8 C9 H9 118.2 . . ? C10 C10 C7 126.3(4) 2_766 . ? C10 C10 H10 116.8 2_766 . ? C7 C10 H10 116.8 . . ? N3 C11 C12 123.5(3) . . ? N3 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C13 119.2(3) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C12 C13 C14 117.0(3) . . ? C12 C13 C16 123.3(3) . . ? C14 C13 C16 119.8(3) . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? N3 C15 C14 122.6(3) . . ? N3 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? C16 C16 C13 124.4(4) 2_666 . ? C16 C16 H16 117.8 2_666 . ? C13 C16 H16 117.8 . . ? 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 Zn1 O3 C4 -136(56) 2_765 . . . ? N2 Zn1 O3 C4 83.56(19) 2_765 . . . ? N2 Zn1 O3 C4 -96.44(19) . . . . ? N1 Zn1 O3 C4 176.09(17) 2_765 . . . ? N1 Zn1 O3 C4 -3.91(17) . . . . ? O5 Zn2 O4 C4 -140.7(2) 2_675 . . . ? O5 Zn2 O4 C4 39.3(2) . . . . ? O4 Zn2 O4 C4 -36(19) 2_675 . . . ? N3 Zn2 O4 C4 -51.4(2) . . . . ? N3 Zn2 O4 C4 128.6(2) 2_675 . . . ? O3 Zn1 N1 C3 9.88(15) . . . . ? O3 Zn1 N1 C3 -170.12(15) 2_765 . . . ? N2 Zn1 N1 C3 -80.68(16) 2_765 . . . ? N2 Zn1 N1 C3 99.32(16) . . . . ? N1 Zn1 N1 C3 -84(3) 2_765 . . . ? O3 Zn1 N1 C2 179.8(2) . . . . ? O3 Zn1 N1 C2 -0.2(2) 2_765 . . . ? N2 Zn1 N1 C2 89.3(2) 2_765 . . . ? N2 Zn1 N1 C2 -90.7(2) . . . . ? N1 Zn1 N1 C2 85(3) 2_765 . . . ? O3 Zn1 N2 C5 144.5(2) . . . . ? O3 Zn1 N2 C5 -35.5(2) 2_765 . . . ? N2 Zn1 N2 C5 55(100) 2_765 . . . ? N1 Zn1 N2 C5 -111.7(2) 2_765 . . . ? N1 Zn1 N2 C5 68.3(2) . . . . ? O3 Zn1 N2 C9 -40.6(2) . . . . ? O3 Zn1 N2 C9 139.4(2) 2_765 . . . ? N2 Zn1 N2 C9 -131(88) 2_765 . . . ? N1 Zn1 N2 C9 63.2(2) 2_765 . . . ? N1 Zn1 N2 C9 -116.8(2) . . . . ? O5 Zn2 N3 C15 -122.0(3) 2_675 . . . ? O5 Zn2 N3 C15 58.0(3) . . . . ? O4 Zn2 N3 C15 151.4(2) . . . . ? O4 Zn2 N3 C15 -28.6(2) 2_675 . . . ? N3 Zn2 N3 C15 11(64) 2_675 . . . ? O5 Zn2 N3 C11 57.4(3) 2_675 . . . ? O5 Zn2 N3 C11 -122.6(3) . . . . ? O4 Zn2 N3 C11 -29.3(3) . . . . ? O4 Zn2 N3 C11 150.7(3) 2_675 . . . ? N3 Zn2 N3 C11 -169(64) 2_675 . . . ? C3 N1 C2 C3 1.1(4) . . . 2_665 ? Zn1 N1 C2 C3 -167.98(16) . . . 2_665 ? C3 N1 C2 C1 -178.8(2) . . . . ? Zn1 N1 C2 C1 12.1(3) . . . . ? O2 C1 C2 N1 96.0(3) . . . . ? O1 C1 C2 N1 -81.0(3) . . . . ? O2 C1 C2 C3 -83.9(3) . . . 2_665 ? O1 C1 C2 C3 99.1(3) . . . 2_665 ? C2 N1 C3 C2 -1.1(4) . . . 2_665 ? Zn1 N1 C3 C2 170.62(18) . . . 2_665 ? C2 N1 C3 C4 174.1(2) . . . . ? Zn1 N1 C3 C4 -14.1(2) . . . . ? Zn2 O4 C4 O3 -42.8(4) . . . . ? Zn2 O4 C4 C3 133.51(18) . . . . ? Zn1 O3 C4 O4 173.72(19) . . . . ? Zn1 O3 C4 C3 -2.5(3) . . . . ? N1 C3 C4 O4 -164.1(2) . . . . ? C2 C3 C4 O4 11.2(3) 2_665 . . . ? N1 C3 C4 O3 12.5(3) . . . . ? C2 C3 C4 O3 -172.2(2) 2_665 . . . ? C9 N2 C5 C6 -0.8(5) . . . . ? Zn1 N2 C5 C6 174.3(3) . . . . ? N2 C5 C6 C7 -1.4(5) . . . . ? C5 C6 C7 C8 2.6(5) . . . . ? C5 C6 C7 C10 -177.9(3) . . . . ? C6 C7 C8 C9 -1.7(5) . . . . ? C10 C7 C8 C9 178.8(3) . . . . ? C5 N2 C9 C8 1.7(4) . . . . ? Zn1 N2 C9 C8 -173.5(2) . . . . ? C7 C8 C9 N2 -0.4(5) . . . . ? C6 C7 C10 C10 178.3(5) . . . 2_766 ? C8 C7 C10 C10 -2.3(8) . . . 2_766 ? C15 N3 C11 C12 -1.6(5) . . . . ? Zn2 N3 C11 C12 179.1(3) . . . . ? N3 C11 C12 C13 1.8(5) . . . . ? C11 C12 C13 C14 0.0(5) . . . . ? C11 C12 C13 C16 179.6(3) . . . . ? C12 C13 C14 C15 -1.8(5) . . . . ? C16 C13 C14 C15 178.6(3) . . . . ? C11 N3 C15 C14 -0.4(5) . . . . ? Zn2 N3 C15 C14 179.0(3) . . . . ? C13 C14 C15 N3 2.1(5) . . . . ? C12 C13 C16 C16 14.4(7) . . . 2_666 ? C14 C13 C16 C16 -166.0(5) . . . 2_666 ? 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 O5 H5A O1 0.838(10) 1.96(2) 2.681(3) 144(3) 2_765 O5 H5A O3 0.838(10) 2.50(3) 3.121(3) 132(3) . O5 H5B O1 0.836(10) 1.850(13) 2.669(3) 166(4) 1_565 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.559 _refine_diff_density_min -0.663 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 972281' ####################################################################### # # 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_r91028g _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 Cu2 N3 O13' _chemical_formula_weight 624.45 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.349(3) _cell_length_b 16.979(3) _cell_length_c 17.583(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.86(3) _cell_angle_gamma 90.00 _cell_volume 4497.4(16) _cell_formula_units_Z 8 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.399 _cell_measurement_theta_max 27.188 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.827 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2480 _exptl_absorpt_coefficient_mu 1.969 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8274 _exptl_absorpt_correction_T_max 0.9254 _exptl_absorpt_process_details CRYSALISPRO _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14906 _diffrn_reflns_av_R_equivalents 0.1512 _diffrn_reflns_av_sigmaI/netI 0.1333 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3913 _reflns_number_gt 2848 _reflns_threshold_expression >2sigma(I) _computing_data_collection CRYSALISPRO _computing_cell_refinement CRYSALISPRO _computing_data_reduction CRYSALISPRO _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^)+(0.0770P)^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 SHELXL _refine_ls_extinction_coef 0.00316(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3913 _refine_ls_number_parameters 344 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0985 _refine_ls_R_factor_gt 0.0757 _refine_ls_wR_factor_ref 0.1893 _refine_ls_wR_factor_gt 0.1741 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.056 _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 0.66630(4) 0.10210(3) 0.83562(3) 0.02213(16) Uani 1 1 d . . . Cu2 Cu 0.50536(4) 0.71034(3) 0.60943(3) 0.02244(16) Uani 1 1 d . . . O1 O 0.8640(2) 0.02352(17) 1.03895(18) 0.0261(9) Uani 1 1 d . . . O2 O 0.7728(2) 0.10519(17) 0.94312(19) 0.0253(9) Uani 1 1 d . . . O3 O 0.5811(2) 0.06204(17) 0.72434(18) 0.0254(9) Uani 1 1 d . . . O4 O 0.5206(2) -0.04945(18) 0.6608(2) 0.0311(10) Uani 1 1 d . . . O5 O 0.6582(2) -0.1686(2) 0.6601(2) 0.0347(10) Uani 1 1 d . . . O6 O 0.5796(2) -0.24030(17) 0.71463(18) 0.0299(10) Uani 1 1 d . . . O7 O 0.91502(19) -0.16406(16) 1.00954(17) 0.0195(8) Uani 1 1 d . . . O8 O 0.8224(2) -0.15464(18) 1.07533(17) 0.0257(8) Uani 1 1 d . . . O9 O 0.5706(2) 0.12038(19) 0.9004(2) 0.0357(10) Uani 1 1 d . . . H9A H 0.5156 0.1103 0.8753 0.043 Uiso 1 1 d R . . H9B H 0.5900 0.1375 0.9497 0.043 Uiso 1 1 d R . . O10 O 0.4493(2) 0.81320(17) 0.5764(2) 0.0312(10) Uani 1 1 d . . . H10A H 0.4036 0.8178 0.5319 0.037 Uiso 1 1 d R . . H10B H 0.4705 0.8534 0.6065 0.037 Uiso 1 1 d R . . O11 O 0.5997(2) 0.7290(2) 0.5298(2) 0.0388(10) Uani 1 1 d . . . N1 N 0.6892(2) -0.0089(2) 0.8515(2) 0.0219(10) Uani 1 1 d . . . N2 N 0.6538(3) 0.2125(2) 0.8017(2) 0.0250(10) Uani 1 1 d . . . N3 N 0.5549(3) 0.6046(2) 0.6558(2) 0.0231(10) Uani 1 1 d . . . C1 C 0.8012(3) 0.0361(3) 0.9745(3) 0.0224(12) Uani 1 1 d . . . C2 C 0.7528(3) -0.0327(2) 0.9215(3) 0.0208(12) Uani 1 1 d . . . C3 C 0.7725(3) -0.1134(3) 0.9339(3) 0.0203(11) Uani 1 1 d . . . C4 C 0.7274(3) -0.1641(2) 0.8690(3) 0.0197(11) Uani 1 1 d . . . H4 H 0.7381 -0.2180 0.8759 0.024 Uiso 1 1 calc R . . C5 C 0.6671(3) -0.1362(3) 0.7945(3) 0.0225(12) Uani 1 1 d . . . C6 C 0.6460(3) -0.0553(3) 0.7877(3) 0.0209(11) Uani 1 1 d . . . C7 C 0.5769(3) -0.0130(3) 0.7171(3) 0.0234(12) Uani 1 1 d . . . C8 C 0.8423(3) -0.1459(2) 1.0139(3) 0.0222(12) Uani 1 1 d . . . C9 C 0.6323(3) -0.1862(3) 0.7162(3) 0.0279(13) Uani 1 1 d . . . C10 C 0.6322(3) 0.2304(3) 0.7220(3) 0.0272(13) Uani 1 1 d . . . H10 H 0.6298 0.1901 0.6854 0.033 Uiso 1 1 calc R . . C11 C 0.6134(3) 0.3059(3) 0.6923(3) 0.0268(12) Uani 1 1 d . . . H11 H 0.5979 0.3157 0.6364 0.032 Uiso 1 1 calc R . . C12 C 0.6175(3) 0.3688(2) 0.7463(3) 0.0198(11) Uani 1 1 d . . . C13 C 0.6431(3) 0.3481(3) 0.8306(3) 0.0280(13) Uani 1 1 d . . . H13 H 0.6489 0.3870 0.8696 0.034 Uiso 1 1 calc R . . C14 C 0.6589(3) 0.2720(3) 0.8543(3) 0.0278(13) Uani 1 1 d . . . H14 H 0.6742 0.2601 0.9098 0.033 Uiso 1 1 calc R . . C15 C 0.5994(3) 0.4499(3) 0.7166(3) 0.0224(12) Uani 1 1 d . . . C16 C 0.5658(3) 0.4674(3) 0.6330(3) 0.0260(13) Uani 1 1 d . . . H16 H 0.5573 0.4271 0.5949 0.031 Uiso 1 1 calc R . . C17 C 0.5449(3) 0.5430(3) 0.6058(3) 0.0247(12) Uani 1 1 d . . . H17 H 0.5224 0.5520 0.5492 0.030 Uiso 1 1 calc R . . C18 C 0.5931(4) 0.5903(3) 0.7376(3) 0.0326(14) Uani 1 1 d . . . H18 H 0.6045 0.6324 0.7740 0.039 Uiso 1 1 calc R . . C19 C 0.6156(4) 0.5158(3) 0.7689(3) 0.0319(14) Uani 1 1 d . . . H19 H 0.6420 0.5088 0.8258 0.038 Uiso 1 1 calc R . . O12 O 0.8440(2) 0.37203(18) 0.42972(19) 0.0280(9) Uani 1 1 d . . . O13 O 0.1471(7) 0.4636(4) 0.5576(5) 0.062(3) Uani 0.50 1 d PU A 1 O13' O 0.0815(6) 0.4776(5) 0.5277(5) 0.057(2) Uani 0.50 1 d PU B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0269(3) 0.0191(3) 0.0226(3) -0.0002(2) 0.0120(2) 0.0016(2) Cu2 0.0283(3) 0.0193(3) 0.0178(3) -0.0010(2) 0.0068(2) -0.0025(2) O1 0.0281(16) 0.0296(17) 0.0231(16) -0.0017(13) 0.0125(13) 0.0003(14) O2 0.0294(17) 0.0234(16) 0.0245(16) -0.0023(12) 0.0119(13) -0.0004(13) O3 0.0276(16) 0.0203(16) 0.0243(17) 0.0013(13) 0.0058(13) 0.0002(13) O4 0.0298(17) 0.0326(18) 0.0271(18) -0.0006(14) 0.0068(14) 0.0010(15) O5 0.0363(18) 0.048(2) 0.0266(17) -0.0071(15) 0.0194(14) -0.0058(16) O6 0.0408(19) 0.0208(16) 0.0188(17) -0.0017(13) 0.0015(15) -0.0107(15) O7 0.0191(14) 0.0222(16) 0.0182(15) -0.0012(12) 0.0084(12) 0.0022(12) O8 0.0322(17) 0.0334(18) 0.0149(15) 0.0028(13) 0.0129(13) 0.0036(14) O9 0.0302(18) 0.047(2) 0.0306(19) -0.0004(15) 0.0124(15) -0.0054(16) O10 0.0317(18) 0.0255(17) 0.0284(18) -0.0070(14) 0.0030(15) 0.0015(15) O11 0.0362(19) 0.048(2) 0.036(2) -0.0097(16) 0.0187(16) 0.0009(17) N1 0.0239(18) 0.0193(19) 0.0231(19) -0.0001(15) 0.0096(15) -0.0012(15) N2 0.033(2) 0.023(2) 0.024(2) -0.0027(15) 0.0153(16) -0.0016(16) N3 0.028(2) 0.0211(19) 0.0164(19) -0.0026(15) 0.0045(16) -0.0058(16) C1 0.021(2) 0.027(2) 0.020(2) -0.0004(18) 0.0085(18) -0.0021(19) C2 0.023(2) 0.023(2) 0.020(2) -0.0019(17) 0.0113(18) -0.0027(18) C3 0.023(2) 0.026(2) 0.017(2) 0.0005(17) 0.0122(17) 0.0018(19) C4 0.020(2) 0.018(2) 0.023(2) 0.0027(17) 0.0105(17) 0.0026(18) C5 0.022(2) 0.025(2) 0.021(2) -0.0050(18) 0.0081(18) -0.0030(19) C6 0.023(2) 0.023(2) 0.020(2) 0.0003(18) 0.0114(17) 0.0001(19) C7 0.025(2) 0.031(3) 0.019(2) -0.0039(18) 0.0133(18) 0.000(2) C8 0.034(3) 0.013(2) 0.018(2) -0.0081(17) 0.0084(19) -0.0053(19) C9 0.026(2) 0.032(3) 0.027(3) 0.003(2) 0.012(2) 0.007(2) C10 0.040(3) 0.025(2) 0.016(2) -0.0054(18) 0.009(2) -0.005(2) C11 0.039(3) 0.031(3) 0.018(2) 0.0003(18) 0.0185(19) -0.002(2) C12 0.029(2) 0.018(2) 0.020(2) -0.0030(17) 0.0182(17) -0.0034(18) C13 0.046(3) 0.022(2) 0.017(2) -0.0059(18) 0.013(2) -0.003(2) C14 0.035(3) 0.035(3) 0.013(2) -0.0017(19) 0.0096(19) 0.006(2) C15 0.028(2) 0.023(2) 0.019(2) -0.0016(18) 0.0119(18) 0.001(2) C16 0.031(2) 0.032(3) 0.016(2) -0.0059(18) 0.0115(19) 0.007(2) C17 0.030(2) 0.029(3) 0.017(2) 0.0003(19) 0.0114(19) 0.007(2) C18 0.057(3) 0.024(3) 0.022(2) -0.0007(19) 0.020(2) -0.002(2) C19 0.051(3) 0.027(3) 0.019(2) 0.0018(19) 0.015(2) 0.003(2) O12 0.0309(17) 0.0346(18) 0.0204(16) -0.0003(13) 0.0121(13) 0.0027(15) O13 0.114(7) 0.033(4) 0.045(4) -0.005(3) 0.037(4) 0.008(4) O13' 0.076(5) 0.071(5) 0.043(4) -0.022(4) 0.043(4) -0.040(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 Cu1 N1 1.921(4) . ? Cu1 N2 1.953(4) . ? Cu1 O2 2.013(3) . ? Cu1 O3 2.028(3) . ? Cu1 O9 2.286(4) . ? Cu2 O10 1.953(3) . ? Cu2 O6 1.963(3) 1_565 ? Cu2 O7 1.967(3) 8_455 ? Cu2 N3 2.007(3) . ? O1 C1 1.216(5) . ? O2 C1 1.302(5) . ? O3 C7 1.279(5) . ? O4 C7 1.227(5) . ? O5 C9 1.252(7) . ? O6 C9 1.252(6) . ? O6 Cu2 1.963(3) 1_545 ? O7 C8 1.258(6) . ? O7 Cu2 1.967(3) 8_556 ? O8 C8 1.253(6) . ? O9 H9A 0.8500 . ? O9 H9B 0.8501 . ? O10 H10A 0.8499 . ? O10 H10B 0.8499 . ? N1 C6 1.328(5) . ? N1 C2 1.330(5) . ? N2 C10 1.341(6) . ? N2 C14 1.351(6) . ? N3 C17 1.335(6) . ? N3 C18 1.349(6) . ? C1 C2 1.512(6) . ? C2 C3 1.405(6) . ? C3 C4 1.391(6) . ? C3 C8 1.529(6) . ? C4 C5 1.382(6) . ? C4 H4 0.9300 . ? C5 C6 1.410(6) . ? C5 C9 1.527(6) . ? C6 C7 1.497(6) . ? C10 C11 1.374(6) . ? C10 H10 0.9300 . ? C11 C12 1.413(6) . ? C11 H11 0.9300 . ? C12 C13 1.418(6) . ? C12 C15 1.462(6) . ? C13 C14 1.351(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.386(6) . ? C15 C19 1.408(6) . ? C16 C17 1.365(6) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.371(6) . ? C18 H18 0.9300 . ? C19 H19 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 N1 Cu1 N2 167.77(19) . . ? N1 Cu1 O2 80.83(13) . . ? N2 Cu1 O2 102.20(14) . . ? N1 Cu1 O3 80.39(13) . . ? N2 Cu1 O3 94.37(14) . . ? O2 Cu1 O3 159.09(13) . . ? N1 Cu1 O9 101.14(15) . . ? N2 Cu1 O9 90.64(16) . . ? O2 Cu1 O9 92.23(13) . . ? O3 Cu1 O9 100.34(13) . . ? O10 Cu2 O6 86.87(13) . 1_565 ? O10 Cu2 O7 89.36(12) . 8_455 ? O6 Cu2 O7 170.79(16) 1_565 8_455 ? O10 Cu2 N3 171.55(18) . . ? O6 Cu2 N3 89.71(13) 1_565 . ? O7 Cu2 N3 92.86(13) 8_455 . ? C1 O2 Cu1 114.2(2) . . ? C7 O3 Cu1 114.8(2) . . ? C9 O6 Cu2 120.1(3) . 1_545 ? C8 O7 Cu2 116.3(3) . 8_556 ? Cu1 O9 H9A 120.2 . . ? Cu1 O9 H9B 119.8 . . ? H9A O9 H9B 120.0 . . ? Cu2 O10 H10A 119.9 . . ? Cu2 O10 H10B 120.1 . . ? H10A O10 H10B 120.0 . . ? C6 N1 C2 124.8(4) . . ? C6 N1 Cu1 116.7(3) . . ? C2 N1 Cu1 118.1(3) . . ? C10 N2 C14 117.8(4) . . ? C10 N2 Cu1 119.4(3) . . ? C14 N2 Cu1 122.6(3) . . ? C17 N3 C18 116.6(4) . . ? C17 N3 Cu2 120.5(3) . . ? C18 N3 Cu2 122.7(3) . . ? O1 C1 O2 125.9(4) . . ? O1 C1 C2 119.2(4) . . ? O2 C1 C2 114.9(3) . . ? N1 C2 C3 119.3(4) . . ? N1 C2 C1 111.7(4) . . ? C3 C2 C1 128.7(4) . . ? C4 C3 C2 117.4(4) . . ? C4 C3 C8 119.9(4) . . ? C2 C3 C8 122.6(4) . . ? C5 C4 C3 121.4(4) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.4(4) . . ? C4 C5 C9 122.9(4) . . ? C6 C5 C9 118.1(4) . . ? N1 C6 C5 118.2(4) . . ? N1 C6 C7 113.4(4) . . ? C5 C6 C7 128.3(4) . . ? O4 C7 O3 125.3(4) . . ? O4 C7 C6 121.0(4) . . ? O3 C7 C6 113.7(4) . . ? O8 C8 O7 126.3(4) . . ? O8 C8 C3 119.0(4) . . ? O7 C8 C3 114.7(4) . . ? O5 C9 O6 126.8(4) . . ? O5 C9 C5 117.2(4) . . ? O6 C9 C5 116.1(5) . . ? N2 C10 C11 122.6(4) . . ? N2 C10 H10 118.7 . . ? C11 C10 H10 118.7 . . ? C10 C11 C12 120.2(4) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 115.7(4) . . ? C11 C12 C15 121.4(4) . . ? C13 C12 C15 122.9(4) . . ? C14 C13 C12 120.2(4) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 N2 123.4(4) . . ? C13 C14 H14 118.3 . . ? N2 C14 H14 118.3 . . ? C16 C15 C19 114.8(4) . . ? C16 C15 C12 121.5(4) . . ? C19 C15 C12 123.7(4) . . ? C17 C16 C15 121.0(4) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? N3 C17 C16 123.8(4) . . ? N3 C17 H17 118.1 . . ? C16 C17 H17 118.1 . . ? N3 C18 C19 122.4(4) . . ? N3 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? C18 C19 C15 121.1(4) . . ? C18 C19 H19 119.4 . . ? C15 C19 H19 119.4 . . ? 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 N1 Cu1 O2 C1 -5.0(4) . . . . ? N2 Cu1 O2 C1 -172.9(4) . . . . ? O3 Cu1 O2 C1 -31.3(6) . . . . ? O9 Cu1 O2 C1 96.0(3) . . . . ? N1 Cu1 O3 C7 4.0(3) . . . . ? N2 Cu1 O3 C7 172.9(4) . . . . ? O2 Cu1 O3 C7 30.4(6) . . . . ? O9 Cu1 O3 C7 -95.7(3) . . . . ? N2 Cu1 N1 C6 -62.8(9) . . . . ? O2 Cu1 N1 C6 -168.2(4) . . . . ? O3 Cu1 N1 C6 2.6(4) . . . . ? O9 Cu1 N1 C6 101.3(4) . . . . ? N2 Cu1 N1 C2 110.5(7) . . . . ? O2 Cu1 N1 C2 5.1(4) . . . . ? O3 Cu1 N1 C2 175.9(4) . . . . ? O9 Cu1 N1 C2 -85.3(4) . . . . ? N1 Cu1 N2 C10 36.9(9) . . . . ? O2 Cu1 N2 C10 140.0(4) . . . . ? O3 Cu1 N2 C10 -27.1(4) . . . . ? O9 Cu1 N2 C10 -127.5(4) . . . . ? N1 Cu1 N2 C14 -148.7(6) . . . . ? O2 Cu1 N2 C14 -45.5(4) . . . . ? O3 Cu1 N2 C14 147.3(4) . . . . ? O9 Cu1 N2 C14 46.9(4) . . . . ? O10 Cu2 N3 C17 129.5(9) . . . . ? O6 Cu2 N3 C17 -164.4(4) 1_565 . . . ? O7 Cu2 N3 C17 24.4(4) 8_455 . . . ? O10 Cu2 N3 C18 -45.1(11) . . . . ? O6 Cu2 N3 C18 21.0(4) 1_565 . . . ? O7 Cu2 N3 C18 -150.1(4) 8_455 . . . ? Cu1 O2 C1 O1 -179.6(4) . . . . ? Cu1 O2 C1 C2 4.1(5) . . . . ? C6 N1 C2 C3 -5.6(8) . . . . ? Cu1 N1 C2 C3 -178.4(4) . . . . ? C6 N1 C2 C1 168.4(5) . . . . ? Cu1 N1 C2 C1 -4.3(6) . . . . ? O1 C1 C2 N1 -176.7(5) . . . . ? O2 C1 C2 N1 0.0(6) . . . . ? O1 C1 C2 C3 -3.3(8) . . . . ? O2 C1 C2 C3 173.3(5) . . . . ? N1 C2 C3 C4 4.0(7) . . . . ? C1 C2 C3 C4 -168.9(5) . . . . ? N1 C2 C3 C8 -177.7(5) . . . . ? C1 C2 C3 C8 9.3(8) . . . . ? C2 C3 C4 C5 1.5(8) . . . . ? C8 C3 C4 C5 -176.8(5) . . . . ? C3 C4 C5 C6 -5.6(8) . . . . ? C3 C4 C5 C9 165.7(5) . . . . ? C2 N1 C6 C5 1.4(8) . . . . ? Cu1 N1 C6 C5 174.3(4) . . . . ? C2 N1 C6 C7 179.4(5) . . . . ? Cu1 N1 C6 C7 -7.7(6) . . . . ? C4 C5 C6 N1 4.2(7) . . . . ? C9 C5 C6 N1 -167.5(5) . . . . ? C4 C5 C6 C7 -173.4(5) . . . . ? C9 C5 C6 C7 14.9(8) . . . . ? Cu1 O3 C7 O4 168.0(4) . . . . ? Cu1 O3 C7 C6 -8.9(5) . . . . ? N1 C6 C7 O4 -166.1(5) . . . . ? C5 C6 C7 O4 11.6(8) . . . . ? N1 C6 C7 O3 11.0(6) . . . . ? C5 C6 C7 O3 -171.3(5) . . . . ? Cu2 O7 C8 O8 -0.1(5) 8_556 . . . ? Cu2 O7 C8 C3 -177.5(3) 8_556 . . . ? C4 C3 C8 O8 -102.2(5) . . . . ? C2 C3 C8 O8 79.6(6) . . . . ? C4 C3 C8 O7 75.5(6) . . . . ? C2 C3 C8 O7 -102.7(5) . . . . ? Cu2 O6 C9 O5 -16.0(7) 1_545 . . . ? Cu2 O6 C9 C5 163.3(3) 1_545 . . . ? C4 C5 C9 O5 -109.2(6) . . . . ? C6 C5 C9 O5 62.1(6) . . . . ? C4 C5 C9 O6 71.5(6) . . . . ? C6 C5 C9 O6 -117.2(5) . . . . ? C14 N2 C10 C11 -1.5(8) . . . . ? Cu1 N2 C10 C11 173.2(4) . . . . ? N2 C10 C11 C12 0.8(8) . . . . ? C10 C11 C12 C13 1.0(7) . . . . ? C10 C11 C12 C15 178.8(5) . . . . ? C11 C12 C13 C14 -2.1(7) . . . . ? C15 C12 C13 C14 -179.9(5) . . . . ? C12 C13 C14 N2 1.6(8) . . . . ? C10 N2 C14 C13 0.3(8) . . . . ? Cu1 N2 C14 C13 -174.2(4) . . . . ? C11 C12 C15 C16 9.1(7) . . . . ? C13 C12 C15 C16 -173.3(5) . . . . ? C11 C12 C15 C19 -169.9(5) . . . . ? C13 C12 C15 C19 7.7(8) . . . . ? C19 C15 C16 C17 -4.3(7) . . . . ? C12 C15 C16 C17 176.6(5) . . . . ? C18 N3 C17 C16 4.1(8) . . . . ? Cu2 N3 C17 C16 -170.7(4) . . . . ? C15 C16 C17 N3 0.2(8) . . . . ? C17 N3 C18 C19 -4.1(8) . . . . ? Cu2 N3 C18 C19 170.7(4) . . . . ? N3 C18 C19 C15 -0.2(9) . . . . ? C16 C15 C19 C18 4.4(8) . . . . ? C12 C15 C19 C18 -176.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.059 _refine_diff_density_min -1.222 _refine_diff_density_rms 0.189 _database_code_depnum_ccdc_archive 'CCDC 972282' ####################################################################### # # 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_r91031d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 Cu2 N3 O12' _chemical_formula_weight 606.44 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 7.7911(16) _cell_length_b 17.630(4) _cell_length_c 15.874(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.99(3) _cell_angle_gamma 90.00 _cell_volume 2164.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 6586 _cell_measurement_theta_min 2.310 _cell_measurement_theta_max 27.920 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.861 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 2.040 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8538 _exptl_absorpt_correction_T_max 0.9228 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19348 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.86 _reflns_number_total 5129 _reflns_number_gt 4310 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0488P)^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 5129 _refine_ls_number_parameters 357 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.069 _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 0.65401(4) 0.030889(15) -0.128970(15) 0.00904(8) Uani 1 1 d . . . Cu2 Cu 0.60289(4) 0.329938(15) 0.219379(15) 0.00844(8) Uani 1 1 d . . . O1 O 0.7128(2) -0.07483(9) -0.08389(9) 0.0124(3) Uani 1 1 d . . . O2 O 0.8328(2) -0.13513(9) 0.03337(10) 0.0153(4) Uani 1 1 d . . . O3 O 1.1080(2) -0.05929(9) 0.18183(10) 0.0128(3) Uani 1 1 d . . . O4 O 0.8479(2) -0.07198(8) 0.22676(9) 0.0098(3) Uani 1 1 d . . . O5 O 0.8876(2) 0.27094(10) 0.13639(11) 0.0187(4) Uani 1 1 d . . . O6 O 0.6220(2) 0.23464(9) 0.15998(9) 0.0113(3) Uani 1 1 d . . . O7 O 0.6131(2) 0.24449(9) -0.04349(9) 0.0167(4) Uani 1 1 d . . . O8 O 0.5895(2) 0.14245(9) -0.12950(9) 0.0133(3) Uani 1 1 d . . . O9 O 0.7667(2) 0.28854(9) 0.31917(10) 0.0141(4) Uani 1 1 d D . . O10 O 0.4046(2) 0.28073(10) 0.29221(11) 0.0160(4) Uani 1 1 d D . . N1 N 0.7320(2) 0.05502(10) -0.01306(11) 0.0093(4) Uani 1 1 d . . . N2 N 0.4449(3) 0.37255(11) 0.12049(11) 0.0107(4) Uani 1 1 d . . . N3 N -0.0340(2) 0.50022(11) -0.26107(11) 0.0097(4) Uani 1 1 d . . . C1 C 0.7833(3) -0.07760(13) -0.00567(14) 0.0113(4) Uani 1 1 d . . . C2 C 0.8005(3) -0.00071(12) 0.03747(13) 0.0086(4) Uani 1 1 d . . . C3 C 0.8722(3) 0.01590(12) 0.11989(13) 0.0086(4) Uani 1 1 d . . . C4 C 0.8605(3) 0.09068(12) 0.14829(13) 0.0099(4) Uani 1 1 d . . . H4 H 0.9039 0.1028 0.2038 0.012 Uiso 1 1 calc R . . C5 C 0.7851(3) 0.14713(13) 0.09493(13) 0.0098(4) Uani 1 1 d . . . C6 C 0.7223(3) 0.12678(12) 0.01176(13) 0.0098(4) Uani 1 1 d . . . C7 C 0.6350(3) 0.17750(13) -0.05779(14) 0.0113(5) Uani 1 1 d . . . C8 C 0.9525(3) -0.04366(12) 0.17987(13) 0.0092(4) Uani 1 1 d . . . C9 C 0.7656(3) 0.22534(12) 0.13134(13) 0.0109(4) Uani 1 1 d . . . C10 C 0.4235(3) 0.44730(13) 0.10556(14) 0.0122(5) Uani 1 1 d . . . H10 H 0.4800 0.4814 0.1442 0.015 Uiso 1 1 calc R . . C11 C 0.3210(3) 0.47580(13) 0.03516(13) 0.0130(5) Uani 1 1 d . . . H11 H 0.3086 0.5279 0.0275 0.016 Uiso 1 1 calc R . . C12 C 0.2364(3) 0.42573(13) -0.02425(14) 0.0116(5) Uani 1 1 d . . . C13 C 0.2505(3) 0.34870(13) -0.00591(14) 0.0155(5) Uani 1 1 d . . . H13 H 0.1897 0.3136 -0.0417 0.019 Uiso 1 1 calc R . . C14 C 0.3554(3) 0.32438(13) 0.06574(14) 0.0135(5) Uani 1 1 d . . . H14 H 0.3645 0.2726 0.0765 0.016 Uiso 1 1 calc R . . C15 C 0.1399(3) 0.45287(13) -0.10514(14) 0.0123(5) Uani 1 1 d . . . C16 C 0.0826(3) 0.52759(13) -0.11799(14) 0.0130(5) Uani 1 1 d . . . H16 H 0.1016 0.5627 -0.0741 0.016 Uiso 1 1 calc R . . C17 C -0.0024(3) 0.54929(14) -0.19576(14) 0.0129(5) Uani 1 1 d . . . H17 H -0.0389 0.5993 -0.2033 0.015 Uiso 1 1 calc R . . C18 C 0.0212(3) 0.42855(13) -0.24962(14) 0.0122(5) Uani 1 1 d . . . H18 H 0.0001 0.3946 -0.2946 0.015 Uiso 1 1 calc R . . C19 C 0.1080(3) 0.40293(13) -0.17408(14) 0.0137(5) Uani 1 1 d . . . H19 H 0.1451 0.3528 -0.1689 0.016 Uiso 1 1 calc R . . O11 O 0.6900(2) 0.30800(10) 0.68742(11) 0.0186(4) Uani 1 1 d D . . O12 O 0.5734(3) 0.37207(11) 0.84281(12) 0.0289(5) Uani 1 1 d D . . H9A H 0.868(2) 0.3048(18) 0.3156(18) 0.044(10) Uiso 1 1 d D . . H9B H 0.722(4) 0.3012(19) 0.3632(14) 0.049(11) Uiso 1 1 d D . . H10A H 0.343(3) 0.3160(12) 0.3104(19) 0.037(10) Uiso 1 1 d D . . H10B H 0.347(4) 0.2480(14) 0.261(2) 0.058(12) Uiso 1 1 d D . . H11A H 0.717(4) 0.3430(13) 0.6545(15) 0.039(10) Uiso 1 1 d D . . H11B H 0.608(3) 0.2794(14) 0.6647(16) 0.039(10) Uiso 1 1 d D . . H12A H 0.631(4) 0.3580(18) 0.8032(16) 0.047(11) Uiso 1 1 d D . . H12B H 0.548(5) 0.325(2) 0.871(2) 0.060(12) Uiso 1 1 d 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 0.01112(15) 0.00891(14) 0.00639(14) -0.00053(9) -0.00176(10) 0.00043(10) Cu2 0.01031(15) 0.00722(14) 0.00721(13) -0.00115(9) -0.00130(10) 0.00102(10) O1 0.0177(9) 0.0108(8) 0.0078(7) -0.0017(6) -0.0029(6) -0.0004(6) O2 0.0250(10) 0.0089(8) 0.0113(8) 0.0004(6) -0.0012(7) 0.0028(7) O3 0.0090(8) 0.0141(8) 0.0151(8) 0.0044(6) 0.0013(6) 0.0004(6) O4 0.0099(8) 0.0102(8) 0.0096(7) 0.0024(6) 0.0020(6) -0.0001(6) O5 0.0185(10) 0.0117(9) 0.0264(9) -0.0026(7) 0.0043(7) -0.0018(7) O6 0.0137(9) 0.0105(8) 0.0095(7) -0.0023(6) 0.0002(6) 0.0023(6) O7 0.0259(10) 0.0109(8) 0.0128(8) 0.0011(6) -0.0001(7) 0.0062(7) O8 0.0168(9) 0.0132(8) 0.0090(7) -0.0014(6) -0.0026(6) 0.0034(7) O9 0.0143(9) 0.0135(9) 0.0132(8) 0.0005(6) -0.0029(7) 0.0009(7) O10 0.0170(9) 0.0138(9) 0.0178(9) -0.0033(7) 0.0045(7) -0.0027(7) N1 0.0106(10) 0.0093(9) 0.0078(9) 0.0017(7) 0.0004(7) 0.0009(7) N2 0.0119(10) 0.0127(10) 0.0070(9) 0.0005(7) -0.0008(7) 0.0020(8) N3 0.0075(9) 0.0126(10) 0.0089(9) 0.0010(7) 0.0002(7) 0.0008(7) C1 0.0117(12) 0.0107(11) 0.0116(11) -0.0022(8) 0.0021(9) -0.0015(9) C2 0.0100(11) 0.0085(10) 0.0075(10) 0.0004(8) 0.0024(8) 0.0011(8) C3 0.0069(11) 0.0092(10) 0.0096(10) 0.0004(8) 0.0006(8) -0.0008(8) C4 0.0113(11) 0.0104(11) 0.0076(10) -0.0008(8) 0.0004(8) -0.0003(9) C5 0.0094(11) 0.0105(11) 0.0097(10) -0.0018(8) 0.0018(8) -0.0016(8) C6 0.0110(11) 0.0105(11) 0.0081(10) 0.0010(8) 0.0017(8) 0.0010(8) C7 0.0125(12) 0.0121(11) 0.0095(10) 0.0010(8) 0.0018(8) 0.0015(9) C8 0.0140(12) 0.0066(10) 0.0061(10) -0.0023(8) -0.0017(8) -0.0012(8) C9 0.0159(12) 0.0086(11) 0.0075(10) 0.0012(8) -0.0010(8) 0.0026(9) C10 0.0149(12) 0.0117(11) 0.0094(10) -0.0030(8) -0.0009(9) 0.0000(9) C11 0.0151(12) 0.0116(11) 0.0117(11) 0.0001(8) -0.0011(9) 0.0033(9) C12 0.0098(11) 0.0156(12) 0.0095(10) 0.0001(8) 0.0009(8) 0.0033(9) C13 0.0187(13) 0.0148(12) 0.0115(11) -0.0019(9) -0.0037(9) -0.0007(10) C14 0.0159(13) 0.0127(12) 0.0110(11) 0.0009(8) -0.0024(9) 0.0001(9) C15 0.0108(11) 0.0160(12) 0.0098(10) 0.0012(9) 0.0000(8) 0.0012(9) C16 0.0140(12) 0.0146(12) 0.0098(10) -0.0019(8) -0.0004(9) 0.0021(9) C17 0.0149(12) 0.0120(11) 0.0115(11) -0.0017(8) 0.0001(9) 0.0024(9) C18 0.0140(12) 0.0112(11) 0.0109(11) -0.0015(8) 0.0001(9) 0.0019(9) C19 0.0163(13) 0.0118(11) 0.0126(11) 0.0003(9) -0.0003(9) 0.0025(9) O11 0.0164(10) 0.0179(9) 0.0214(9) 0.0080(7) 0.0020(7) -0.0003(7) O12 0.0403(13) 0.0247(11) 0.0220(10) 0.0054(8) 0.0050(9) 0.0077(9) _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 1.9141(18) . ? Cu1 N3 1.9537(18) 2_544 ? Cu1 O1 2.0288(16) . ? Cu1 O8 2.0300(17) . ? Cu1 O3 2.1848(17) 3_755 ? Cu2 O6 1.9412(16) . ? Cu2 O4 1.9463(15) 2_655 ? Cu2 N2 2.0183(19) . ? Cu2 O9 2.0443(17) . ? Cu2 O10 2.2158(18) . ? O1 C1 1.296(3) . ? O2 C1 1.226(3) . ? O3 C8 1.239(3) . ? O3 Cu1 2.1848(17) 3_755 ? O4 C8 1.271(3) . ? O4 Cu2 1.9463(15) 2_645 ? O5 C9 1.241(3) . ? O6 C9 1.268(3) . ? O7 C7 1.219(3) . ? O8 C7 1.306(3) . ? O9 H9A 0.850(10) . ? O9 H9B 0.849(10) . ? O10 H10A 0.855(10) . ? O10 H10B 0.853(10) . ? N1 C6 1.330(3) . ? N1 C2 1.338(3) . ? N2 C10 1.346(3) . ? N2 C14 1.347(3) . ? N3 C18 1.340(3) . ? N3 C17 1.350(3) . ? N3 Cu1 1.9537(18) 2_554 ? C1 C2 1.517(3) . ? C2 C3 1.390(3) . ? C3 C4 1.400(3) . ? C3 C8 1.502(3) . ? C4 C5 1.390(3) . ? C4 H4 0.9300 . ? C5 C6 1.398(3) . ? C5 C9 1.510(3) . ? C6 C7 1.516(3) . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 C12 1.397(3) . ? C11 H11 0.9300 . ? C12 C13 1.390(3) . ? C12 C15 1.486(3) . ? C13 C14 1.385(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.398(3) . ? C15 C19 1.403(3) . ? C16 C17 1.382(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.379(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? O11 H11A 0.853(10) . ? O11 H11B 0.858(10) . ? O12 H12A 0.853(10) . ? O12 H12B 0.97(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 N1 Cu1 N3 169.09(8) . 2_544 ? N1 Cu1 O1 80.42(7) . . ? N3 Cu1 O1 97.11(7) 2_544 . ? N1 Cu1 O8 80.68(7) . . ? N3 Cu1 O8 99.97(7) 2_544 . ? O1 Cu1 O8 159.52(6) . . ? N1 Cu1 O3 97.66(7) . 3_755 ? N3 Cu1 O3 93.24(7) 2_544 3_755 ? O1 Cu1 O3 100.39(6) . 3_755 ? O8 Cu1 O3 89.87(7) . 3_755 ? O6 Cu2 O4 163.67(7) . 2_655 ? O6 Cu2 N2 91.14(7) . . ? O4 Cu2 N2 94.58(7) 2_655 . ? O6 Cu2 O9 89.42(7) . . ? O4 Cu2 O9 84.59(7) 2_655 . ? N2 Cu2 O9 178.77(8) . . ? O6 Cu2 O10 90.80(7) . . ? O4 Cu2 O10 103.37(7) 2_655 . ? N2 Cu2 O10 98.84(7) . . ? O9 Cu2 O10 82.25(7) . . ? C1 O1 Cu1 115.06(14) . . ? C8 O3 Cu1 144.33(15) . 3_755 ? C8 O4 Cu2 120.02(14) . 2_645 ? C9 O6 Cu2 114.14(14) . . ? C7 O8 Cu1 114.46(14) . . ? Cu2 O9 H9A 109(2) . . ? Cu2 O9 H9B 105(2) . . ? H9A O9 H9B 116.5(17) . . ? Cu2 O10 H10A 110(2) . . ? Cu2 O10 H10B 108(2) . . ? H10A O10 H10B 114.7(17) . . ? C6 N1 C2 123.64(19) . . ? C6 N1 Cu1 118.26(15) . . ? C2 N1 Cu1 118.03(15) . . ? C10 N2 C14 117.41(19) . . ? C10 N2 Cu2 123.52(15) . . ? C14 N2 Cu2 119.07(15) . . ? C18 N3 C17 118.34(19) . . ? C18 N3 Cu1 119.54(15) . 2_554 ? C17 N3 Cu1 122.12(16) . 2_554 ? O2 C1 O1 125.9(2) . . ? O2 C1 C2 120.4(2) . . ? O1 C1 C2 113.74(19) . . ? N1 C2 C3 119.7(2) . . ? N1 C2 C1 112.25(18) . . ? C3 C2 C1 128.06(19) . . ? C2 C3 C4 117.8(2) . . ? C2 C3 C8 122.56(19) . . ? C4 C3 C8 119.52(18) . . ? C5 C4 C3 121.2(2) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 117.7(2) . . ? C4 C5 C9 118.39(19) . . ? C6 C5 C9 123.8(2) . . ? N1 C6 C5 119.9(2) . . ? N1 C6 C7 112.45(18) . . ? C5 C6 C7 127.7(2) . . ? O7 C7 O8 126.3(2) . . ? O7 C7 C6 119.8(2) . . ? O8 C7 C6 113.96(19) . . ? O3 C8 O4 126.3(2) . . ? O3 C8 C3 120.1(2) . . ? O4 C8 C3 113.51(19) . . ? O5 C9 O6 126.6(2) . . ? O5 C9 C5 120.3(2) . . ? O6 C9 C5 112.9(2) . . ? N2 C10 C11 122.9(2) . . ? N2 C10 H10 118.5 . . ? C11 C10 H10 118.5 . . ? C10 C11 C12 119.6(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 117.2(2) . . ? C13 C12 C15 121.0(2) . . ? C11 C12 C15 121.8(2) . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? N2 C14 C13 122.8(2) . . ? N2 C14 H14 118.6 . . ? C13 C14 H14 118.6 . . ? C16 C15 C19 117.0(2) . . ? C16 C15 C12 123.3(2) . . ? C19 C15 C12 119.7(2) . . ? C17 C16 C15 120.1(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? N3 C17 C16 122.1(2) . . ? N3 C17 H17 118.9 . . ? C16 C17 H17 118.9 . . ? N3 C18 C19 122.8(2) . . ? N3 C18 H18 118.6 . . ? C19 C18 H18 118.6 . . ? C18 C19 C15 119.6(2) . . ? C18 C19 H19 120.2 . . ? C15 C19 H19 120.2 . . ? H11A O11 H11B 113.4(16) . . ? H12A O12 H12B 104(3) . . ? 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 N1 Cu1 O1 C1 -4.86(16) . . . . ? N3 Cu1 O1 C1 -174.11(16) 2_544 . . . ? O8 Cu1 O1 C1 -27.7(3) . . . . ? O3 Cu1 O1 C1 91.25(16) 3_755 . . . ? O4 Cu2 O6 C9 -5.2(3) 2_655 . . . ? N2 Cu2 O6 C9 105.39(15) . . . . ? O9 Cu2 O6 C9 -73.51(15) . . . . ? O10 Cu2 O6 C9 -155.75(15) . . . . ? N1 Cu1 O8 C7 3.11(16) . . . . ? N3 Cu1 O8 C7 172.06(16) 2_544 . . . ? O1 Cu1 O8 C7 26.0(3) . . . . ? O3 Cu1 O8 C7 -94.67(16) 3_755 . . . ? N3 Cu1 N1 C6 -98.6(4) 2_544 . . . ? O1 Cu1 N1 C6 -176.35(18) . . . . ? O8 Cu1 N1 C6 -4.27(17) . . . . ? O3 Cu1 N1 C6 84.34(17) 3_755 . . . ? N3 Cu1 N1 C2 84.4(5) 2_544 . . . ? O1 Cu1 N1 C2 6.66(16) . . . . ? O8 Cu1 N1 C2 178.74(18) . . . . ? O3 Cu1 N1 C2 -92.65(17) 3_755 . . . ? O6 Cu2 N2 C10 -156.81(18) . . . . ? O4 Cu2 N2 C10 7.88(19) 2_655 . . . ? O9 Cu2 N2 C10 -40(4) . . . . ? O10 Cu2 N2 C10 112.20(18) . . . . ? O6 Cu2 N2 C14 23.00(18) . . . . ? O4 Cu2 N2 C14 -172.30(17) 2_655 . . . ? O9 Cu2 N2 C14 140(3) . . . . ? O10 Cu2 N2 C14 -67.99(18) . . . . ? Cu1 O1 C1 O2 -178.07(19) . . . . ? Cu1 O1 C1 C2 2.4(2) . . . . ? C6 N1 C2 C3 -2.4(3) . . . . ? Cu1 N1 C2 C3 174.42(16) . . . . ? C6 N1 C2 C1 176.1(2) . . . . ? Cu1 N1 C2 C1 -7.1(3) . . . . ? O2 C1 C2 N1 -176.8(2) . . . . ? O1 C1 C2 N1 2.8(3) . . . . ? O2 C1 C2 C3 1.6(4) . . . . ? O1 C1 C2 C3 -178.9(2) . . . . ? N1 C2 C3 C4 3.6(3) . . . . ? C1 C2 C3 C4 -174.6(2) . . . . ? N1 C2 C3 C8 -179.5(2) . . . . ? C1 C2 C3 C8 2.2(4) . . . . ? C2 C3 C4 C5 -2.2(3) . . . . ? C8 C3 C4 C5 -179.2(2) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C3 C4 C5 C9 175.8(2) . . . . ? C2 N1 C6 C5 -0.4(3) . . . . ? Cu1 N1 C6 C5 -177.18(16) . . . . ? C2 N1 C6 C7 -178.7(2) . . . . ? Cu1 N1 C6 C7 4.5(3) . . . . ? C4 C5 C6 N1 1.7(3) . . . . ? C9 C5 C6 N1 -174.3(2) . . . . ? C4 C5 C6 C7 179.8(2) . . . . ? C9 C5 C6 C7 3.8(4) . . . . ? Cu1 O8 C7 O7 178.5(2) . . . . ? Cu1 O8 C7 C6 -1.6(2) . . . . ? N1 C6 C7 O7 178.2(2) . . . . ? C5 C6 C7 O7 0.0(4) . . . . ? N1 C6 C7 O8 -1.7(3) . . . . ? C5 C6 C7 O8 -179.8(2) . . . . ? Cu1 O3 C8 O4 -175.78(16) 3_755 . . . ? Cu1 O3 C8 C3 2.0(4) 3_755 . . . ? Cu2 O4 C8 O3 -22.4(3) 2_645 . . . ? Cu2 O4 C8 C3 159.71(13) 2_645 . . . ? C2 C3 C8 O3 88.9(3) . . . . ? C4 C3 C8 O3 -94.3(3) . . . . ? C2 C3 C8 O4 -93.0(3) . . . . ? C4 C3 C8 O4 83.8(3) . . . . ? Cu2 O6 C9 O5 -1.7(3) . . . . ? Cu2 O6 C9 C5 173.04(13) . . . . ? C4 C5 C9 O5 84.0(3) . . . . ? C6 C5 C9 O5 -100.0(3) . . . . ? C4 C5 C9 O6 -91.0(3) . . . . ? C6 C5 C9 O6 85.0(3) . . . . ? C14 N2 C10 C11 -3.0(3) . . . . ? Cu2 N2 C10 C11 176.82(18) . . . . ? N2 C10 C11 C12 -0.7(4) . . . . ? C10 C11 C12 C13 4.5(3) . . . . ? C10 C11 C12 C15 -173.5(2) . . . . ? C11 C12 C13 C14 -4.5(4) . . . . ? C15 C12 C13 C14 173.5(2) . . . . ? C10 N2 C14 C13 2.9(4) . . . . ? Cu2 N2 C14 C13 -176.90(19) . . . . ? C12 C13 C14 N2 0.9(4) . . . . ? C13 C12 C15 C16 162.7(2) . . . . ? C11 C12 C15 C16 -19.4(4) . . . . ? C13 C12 C15 C19 -19.5(3) . . . . ? C11 C12 C15 C19 158.4(2) . . . . ? C19 C15 C16 C17 0.4(4) . . . . ? C12 C15 C16 C17 178.2(2) . . . . ? C18 N3 C17 C16 -0.8(3) . . . . ? Cu1 N3 C17 C16 -179.98(18) 2_554 . . . ? C15 C16 C17 N3 0.5(4) . . . . ? C17 N3 C18 C19 0.3(3) . . . . ? Cu1 N3 C18 C19 179.47(18) 2_554 . . . ? N3 C18 C19 C15 0.6(4) . . . . ? C16 C15 C19 C18 -0.9(3) . . . . ? C12 C15 C19 C18 -178.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.021 _refine_diff_density_min -0.581 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 972283'