Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author ;Dr Robert LaDuca Lyman Briggs College/Chemistry Michigan State University E-30 Holmes Hall East Lansing MI 48825 UNITED STATES OF AMERICA ; _publ_contact_author_email LADUCA@MSU.EDU _publ_contact_author_name 'Dr Robert LaDuca' loop_ _publ_author_name 'Robert LaDuca ' 'Maxwell A Braveman ' 'Ronald M Supkowski ' data_mono1 _database_code_depnum_ccdc_archive 'CCDC 639656' #'0CoPyroDPAFinal.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 Co N6 O12' _chemical_formula_weight 725.53 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' Co Co 0.3494 0.9721 '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 7.268(3) _cell_length_b 20.930(8) _cell_length_c 10.365(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.032(5) _cell_angle_gamma 90.00 _cell_volume 1499.2(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 750 _exptl_absorpt_coefficient_mu 0.651 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.898 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16275 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.07 _reflns_number_total 3423 _reflns_number_gt 3051 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+1.2801P] 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 3423 _refine_ls_number_parameters 241 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0863 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.030 _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 Co1 Co 0.5000 0.0000 0.5000 0.02100(10) Uani 1 2 d S . . O1 O 0.7784(2) 0.01384(9) 0.52329(15) 0.0449(4) Uani 1 1 d D . . H1A H 0.808(4) 0.0154(13) 0.450(2) 0.054 Uiso 1 1 d D . . H1B H 0.868(3) -0.0023(12) 0.585(2) 0.054 Uiso 1 1 d D . . O2 O 0.4350(2) 0.06299(7) 0.32612(13) 0.0321(3) Uani 1 1 d D . . H2A H 0.506(3) 0.0689(11) 0.276(2) 0.038 Uiso 1 1 d D . . H2B H 0.333(3) 0.0838(10) 0.294(2) 0.038 Uiso 1 1 d D . . O3 O 0.8861(2) 0.01815(10) 0.31148(14) 0.0561(5) Uani 1 1 d . . . O4 O 0.6684(2) 0.07567(7) 0.16250(15) 0.0413(4) Uani 1 1 d . . . O5 O 1.1033(2) 0.14224(6) 0.21273(13) 0.0375(3) Uani 1 1 d . . . O6 O 1.0563(3) 0.17407(6) 0.00044(14) 0.0443(4) Uani 1 1 d . . . N1 N 0.5206(2) 0.08210(7) 0.63679(15) 0.0289(3) Uani 1 1 d . . . N2 N 0.5410(3) 0.30712(8) 1.24277(16) 0.0363(4) Uani 1 1 d D . . H2N H 0.543(3) 0.3178(11) 1.3263(18) 0.044 Uiso 1 1 d D . . N3 N 0.5613(3) 0.25037(7) 0.86619(15) 0.0299(3) Uani 1 1 d D . . H3N H 0.563(3) 0.2832(9) 0.815(2) 0.036 Uiso 1 1 d D . . C1 C 0.5305(3) 0.14096(9) 0.5892(2) 0.0372(5) Uani 1 1 d . . . H1 H 0.5265 0.1450 0.4990 0.045 Uiso 1 1 calc R . . C2 C 0.5461(3) 0.19565(9) 0.66410(19) 0.0363(5) Uani 1 1 d . . . H2 H 0.5525 0.2351 0.6246 0.044 Uiso 1 1 calc R . . C3 C 0.5523(3) 0.19217(8) 0.79935(17) 0.0253(3) Uani 1 1 d . . . C4 C 0.5462(3) 0.13137(9) 0.85142(19) 0.0366(5) Uani 1 1 d . . . H4 H 0.5522 0.1259 0.9417 0.044 Uiso 1 1 calc R . . C5 C 0.5310(3) 0.07901(9) 0.76729(19) 0.0361(4) Uani 1 1 d . . . H5 H 0.5279 0.0387 0.8045 0.043 Uiso 1 1 calc R . . C6 C 0.5290(3) 0.34951(10) 1.1442(2) 0.0401(5) Uani 1 1 d . . . H6 H 0.5171 0.3927 1.1610 0.048 Uiso 1 1 calc R . . C7 C 0.5338(3) 0.33063(9) 1.01970(19) 0.0365(5) Uani 1 1 d . . . H7 H 0.5235 0.3609 0.9521 0.044 Uiso 1 1 calc R . . C8 C 0.5542(3) 0.26567(8) 0.99258(18) 0.0267(4) Uani 1 1 d . . . C9 C 0.5683(4) 0.22271(10) 1.0988(2) 0.0430(5) Uani 1 1 d . . . H9 H 0.5826 0.1792 1.0863 0.052 Uiso 1 1 calc R . . C10 C 0.5609(4) 0.24518(10) 1.2207(2) 0.0455(6) Uani 1 1 d . . . H10 H 0.5700 0.2163 1.2906 0.055 Uiso 1 1 calc R . . C11 C 0.9138(2) 0.02310(8) 0.09420(16) 0.0222(3) Uani 1 1 d . . . C12 C 1.0233(2) 0.06403(8) 0.04116(16) 0.0226(3) Uani 1 1 d . . . C13 C 0.8921(3) -0.04038(8) 0.05215(17) 0.0241(3) Uani 1 1 d . . . H13 H 0.8189 -0.0677 0.0875 0.029 Uiso 1 1 calc R . . C15 C 0.8152(3) 0.04272(8) 0.19676(17) 0.0247(3) Uani 1 1 d . . . C16 C 1.0617(3) 0.13253(8) 0.08750(18) 0.0261(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02377(17) 0.02346(17) 0.01769(16) 0.00042(12) 0.00921(12) 0.00072(12) O1 0.0266(7) 0.0864(12) 0.0241(7) 0.0080(7) 0.0112(6) 0.0008(7) O2 0.0383(8) 0.0368(7) 0.0244(6) 0.0081(5) 0.0145(6) 0.0098(6) O3 0.0443(9) 0.1075(15) 0.0221(7) 0.0220(8) 0.0187(6) 0.0334(9) O4 0.0527(9) 0.0445(8) 0.0365(8) 0.0166(6) 0.0283(7) 0.0250(7) O5 0.0651(10) 0.0260(7) 0.0229(6) -0.0030(5) 0.0155(6) 0.0024(6) O6 0.0876(12) 0.0216(7) 0.0280(7) 0.0012(5) 0.0240(7) -0.0045(7) N1 0.0407(9) 0.0242(7) 0.0242(7) -0.0016(6) 0.0137(6) -0.0005(6) N2 0.0512(10) 0.0364(9) 0.0235(8) -0.0049(7) 0.0148(7) 0.0018(8) N3 0.0498(10) 0.0193(7) 0.0225(7) 0.0005(6) 0.0138(7) -0.0010(6) C1 0.0642(14) 0.0286(10) 0.0228(9) -0.0004(7) 0.0194(9) -0.0032(9) C2 0.0634(14) 0.0220(9) 0.0274(9) 0.0022(7) 0.0198(9) -0.0035(9) C3 0.0304(9) 0.0234(8) 0.0226(8) -0.0021(7) 0.0090(7) -0.0005(7) C4 0.0649(14) 0.0259(9) 0.0212(9) -0.0002(7) 0.0167(9) -0.0021(9) C5 0.0609(13) 0.0227(9) 0.0264(9) 0.0016(7) 0.0157(9) -0.0012(8) C6 0.0610(14) 0.0266(9) 0.0330(10) -0.0037(8) 0.0151(10) 0.0076(9) C7 0.0583(13) 0.0243(9) 0.0264(9) 0.0018(7) 0.0123(9) 0.0034(8) C8 0.0336(9) 0.0241(8) 0.0220(8) -0.0020(7) 0.0077(7) -0.0009(7) C9 0.0792(17) 0.0229(9) 0.0293(10) -0.0002(8) 0.0203(10) -0.0006(10) C10 0.0801(17) 0.0324(11) 0.0273(10) 0.0021(8) 0.0215(11) -0.0025(10) C11 0.0294(8) 0.0230(8) 0.0163(7) 0.0033(6) 0.0103(6) 0.0049(6) C12 0.0315(9) 0.0194(8) 0.0180(7) 0.0018(6) 0.0094(6) 0.0028(6) C13 0.0327(9) 0.0221(8) 0.0216(8) 0.0021(6) 0.0141(7) -0.0010(7) C15 0.0315(9) 0.0259(8) 0.0209(8) 0.0003(6) 0.0141(7) 0.0018(7) C16 0.0355(9) 0.0218(8) 0.0237(8) -0.0002(7) 0.0132(7) 0.0014(7) _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 Co1 O1 1.9835(16) . ? Co1 O1 1.9835(16) 3_656 ? Co1 O2 2.1638(14) 3_656 ? Co1 O2 2.1638(14) . ? Co1 N1 2.2032(16) . ? Co1 N1 2.2032(16) 3_656 ? O3 C15 1.251(2) . ? O4 C15 1.227(2) . ? O5 C16 1.255(2) . ? O6 C16 1.245(2) . ? N1 C5 1.333(2) . ? N1 C1 1.337(2) . ? N2 C10 1.332(3) . ? N2 C6 1.335(3) . ? N3 C8 1.365(2) . ? N3 C3 1.393(2) . ? C1 C2 1.368(3) . ? C2 C3 1.390(3) . ? C3 C4 1.388(3) . ? C4 C5 1.384(3) . ? C6 C7 1.360(3) . ? C7 C8 1.405(3) . ? C8 C9 1.400(3) . ? C9 C10 1.365(3) . ? C11 C13 1.392(2) . ? C11 C12 1.393(2) . ? C11 C15 1.511(2) . ? C12 C13 1.388(2) 3_755 ? C12 C16 1.510(2) . ? C13 C12 1.388(2) 3_755 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 180.00(11) . 3_656 ? O1 Co1 O2 92.07(6) . 3_656 ? O1 Co1 O2 87.93(6) 3_656 3_656 ? O1 Co1 O2 87.93(6) . . ? O1 Co1 O2 92.07(6) 3_656 . ? O2 Co1 O2 180.0 3_656 . ? O1 Co1 N1 86.81(7) . . ? O1 Co1 N1 93.19(7) 3_656 . ? O2 Co1 N1 89.16(6) 3_656 . ? O2 Co1 N1 90.84(6) . . ? O1 Co1 N1 93.19(7) . 3_656 ? O1 Co1 N1 86.81(7) 3_656 3_656 ? O2 Co1 N1 90.84(6) 3_656 3_656 ? O2 Co1 N1 89.16(6) . 3_656 ? N1 Co1 N1 180.00(5) . 3_656 ? C5 N1 C1 115.24(16) . . ? C5 N1 Co1 125.90(13) . . ? C1 N1 Co1 118.82(12) . . ? C10 N2 C6 119.99(17) . . ? C8 N3 C3 132.26(15) . . ? N1 C1 C2 124.49(17) . . ? C1 C2 C3 119.96(17) . . ? C4 C3 C2 116.42(16) . . ? C4 C3 N3 127.63(16) . . ? C2 C3 N3 115.95(16) . . ? C5 C4 C3 119.14(17) . . ? N1 C5 C4 124.72(18) . . ? N2 C6 C7 121.19(18) . . ? C6 C7 C8 120.40(18) . . ? N3 C8 C9 126.05(17) . . ? N3 C8 C7 117.16(16) . . ? C9 C8 C7 116.78(17) . . ? C10 C9 C8 119.48(19) . . ? N2 C10 C9 122.14(19) . . ? C13 C11 C12 119.11(15) . . ? C13 C11 C15 116.57(15) . . ? C12 C11 C15 124.31(16) . . ? C13 C12 C11 119.09(16) 3_755 . ? C13 C12 C16 118.80(15) 3_755 . ? C11 C12 C16 122.03(15) . . ? C12 C13 C11 121.80(15) 3_755 . ? O4 C15 O3 124.84(16) . . ? O4 C15 C11 120.55(15) . . ? O3 C15 C11 114.33(16) . . ? O6 C16 O5 125.47(17) . . ? O6 C16 C12 118.11(15) . . ? O5 C16 C12 116.37(15) . . ? 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 O1 H1A O3 0.849(17) 1.703(17) 2.550(2) 175(3) . O1 H1B O3 0.829(16) 1.808(19) 2.597(2) 158(3) 3_756 O2 H2A O4 0.842(16) 1.917(16) 2.758(2) 176(2) . O2 H2B O5 0.836(15) 2.030(16) 2.862(2) 173(2) 1_455 N2 H2N O6 0.890(16) 1.786(17) 2.668(2) 171(2) 4_567 N3 H3N O5 0.872(16) 1.957(16) 2.824(2) 172(2) 4_566 _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.472 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.052 data_mono2 _database_code_depnum_ccdc_archive 'CCDC 656273' #'znpyrodpafinal.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 N3 O10 Zn' _chemical_formula_weight 524.74 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 11.5837(13) _cell_length_b 14.7422(17) _cell_length_c 11.6194(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.319(2) _cell_angle_gamma 90.00 _cell_volume 1938.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 1.338 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.883 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23298 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4730 _reflns_number_gt 4131 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0312P)^2^+1.4398P] 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 4730 _refine_ls_number_parameters 328 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.100 _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 0.992435(17) 0.032054(14) 0.749328(17) 0.00969(7) Uani 1 1 d . . . O1 O 1.22588(13) -0.00999(9) 0.51434(12) 0.0191(3) Uani 1 1 d . . . O1W O 1.32920(13) 0.02148(10) 0.20887(13) 0.0216(3) Uani 1 1 d D . . H1WA H 1.302(2) 0.0108(17) 0.1404(15) 0.026 Uiso 1 1 d D . . H1WB H 1.2761(18) 0.0200(17) 0.2466(19) 0.026 Uiso 1 1 d D . . O2 O 1.13507(12) 0.04651(9) 0.33882(11) 0.0162(3) Uani 1 1 d . . . O2W O 1.35267(15) -0.02162(12) 0.74943(15) 0.0308(4) Uani 1 1 d D . . H2WA H 1.312(2) -0.0157(19) 0.6813(16) 0.037 Uiso 1 1 d D . . H2WB H 1.316(2) -0.0019(19) 0.7968(19) 0.037 Uiso 1 1 d D . . O3 O 1.17778(14) 0.16598(10) 0.77820(12) 0.0248(3) Uani 1 1 d . . . O4 O 1.06749(12) 0.08755(9) 0.63152(11) 0.0164(3) Uani 1 1 d . . . O5 O 1.41177(12) 0.43298(9) 0.66556(11) 0.0162(3) Uani 1 1 d . . . O6 O 1.26971(12) 0.49356(9) 0.52545(12) 0.0186(3) Uani 1 1 d . . . O7 O 1.42475(12) 0.41348(9) 0.37475(11) 0.0155(3) Uani 1 1 d . . . O8 O 1.36036(15) 0.30655(11) 0.24304(12) 0.0273(4) Uani 1 1 d . . . N1 N 1.08528(15) -0.25937(13) 0.45468(15) 0.0217(4) Uani 1 1 d D . . H1N H 1.108(2) -0.2397(16) 0.3918(17) 0.026 Uiso 1 1 d D . . N2 N 0.88361(16) -0.24144(14) 1.03686(16) 0.0257(4) Uani 1 1 d D . . H2N H 0.868(2) -0.2196(17) 1.1019(17) 0.031 Uiso 1 1 d D . . N3 N 0.96535(16) -0.35484(11) 0.74055(14) 0.0186(3) Uani 1 1 d D . . H3N H 0.948(2) -0.4117(12) 0.736(2) 0.022 Uiso 1 1 d D . . C1 C 1.09038(17) -0.20332(14) 0.54691(17) 0.0196(4) Uani 1 1 d . . . H1 H 1.1205 -0.1450 0.5443 0.023 Uiso 1 1 calc R . . C2 C 1.05165(16) -0.23121(13) 0.64464(17) 0.0165(4) Uani 1 1 d . . . H2 H 1.0560 -0.1924 0.7086 0.020 Uiso 1 1 calc R . . C3 C 1.00544(17) -0.31873(13) 0.64721(16) 0.0153(4) Uani 1 1 d . . . C4 C 1.00210(18) -0.37530(14) 0.54907(17) 0.0193(4) Uani 1 1 d . . . H4 H 0.9726 -0.4340 0.5488 0.023 Uiso 1 1 calc R . . C5 C 1.04225(19) -0.34388(15) 0.45411(17) 0.0225(4) Uani 1 1 d . . . H5 H 1.0397 -0.3811 0.3890 0.027 Uiso 1 1 calc R . . C6 C 0.88637(17) -0.18674(15) 0.94460(18) 0.0219(4) Uani 1 1 d . . . H6 H 0.8696 -0.1253 0.9493 0.026 Uiso 1 1 calc R . . C7 C 0.91350(16) -0.22060(13) 0.84420(17) 0.0169(4) Uani 1 1 d . . . H7 H 0.9150 -0.1826 0.7806 0.020 Uiso 1 1 calc R . . C8 C 0.93904(16) -0.31290(13) 0.83803(16) 0.0152(4) Uani 1 1 d . . . C9 C 0.93252(19) -0.36829(15) 0.93461(17) 0.0230(4) Uani 1 1 d . . . H9 H 0.9468 -0.4302 0.9318 0.028 Uiso 1 1 calc R . . C10 C 0.9050(2) -0.33057(16) 1.03291(19) 0.0284(5) Uani 1 1 d . . . H10 H 0.9011 -0.3670 1.0973 0.034 Uiso 1 1 calc R . . C11 C 1.22685(15) 0.15044(12) 0.48212(15) 0.0108(3) Uani 1 1 d . . . C12 C 1.20929(15) 0.19056(12) 0.58617(15) 0.0109(3) Uani 1 1 d . . . C13 C 1.24450(15) 0.28040(12) 0.61086(15) 0.0118(3) Uani 1 1 d . . . H13 H 1.2330 0.3066 0.6804 0.014 Uiso 1 1 calc R . . C14 C 1.29622(15) 0.33205(12) 0.53494(15) 0.0110(3) Uani 1 1 d . . . C15 C 1.31356(15) 0.29188(12) 0.43065(15) 0.0112(3) Uani 1 1 d . . . C16 C 1.27966(15) 0.20181(12) 0.40681(15) 0.0119(3) Uani 1 1 d . . . H16 H 1.2928 0.1751 0.3382 0.014 Uiso 1 1 calc R . . C17 C 1.19274(16) 0.05350(12) 0.44630(16) 0.0119(3) Uani 1 1 d . . . C18 C 1.14784(16) 0.14465(12) 0.67249(16) 0.0128(3) Uani 1 1 d . . . C19 C 1.32842(16) 0.42898(12) 0.57411(15) 0.0122(3) Uani 1 1 d . . . C20 C 1.36955(16) 0.34026(12) 0.34231(16) 0.0129(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01110(11) 0.00858(11) 0.00996(11) -0.00009(7) 0.00356(7) -0.00018(7) O1 0.0261(7) 0.0117(7) 0.0187(7) 0.0020(5) 0.0028(6) 0.0002(6) O1W 0.0215(7) 0.0255(8) 0.0180(7) -0.0021(6) 0.0048(6) -0.0004(6) O2 0.0205(7) 0.0154(7) 0.0123(6) -0.0027(5) 0.0025(5) -0.0063(5) O2W 0.0290(9) 0.0372(10) 0.0255(8) 0.0009(7) 0.0042(7) 0.0065(7) O3 0.0381(9) 0.0264(8) 0.0125(7) -0.0031(6) 0.0110(6) -0.0086(7) O4 0.0172(7) 0.0170(7) 0.0165(6) 0.0018(5) 0.0068(5) -0.0041(5) O5 0.0188(7) 0.0127(6) 0.0153(6) -0.0010(5) -0.0003(5) -0.0030(5) O6 0.0234(7) 0.0117(7) 0.0190(7) 0.0007(5) 0.0007(6) 0.0023(5) O7 0.0191(7) 0.0145(7) 0.0140(6) 0.0015(5) 0.0058(5) -0.0047(5) O8 0.0426(9) 0.0277(8) 0.0164(7) -0.0064(6) 0.0172(7) -0.0129(7) N1 0.0204(8) 0.0294(10) 0.0171(8) 0.0088(7) 0.0083(7) 0.0054(7) N2 0.0221(9) 0.0399(11) 0.0170(9) -0.0128(8) 0.0087(7) -0.0086(8) N3 0.0314(9) 0.0104(8) 0.0165(8) -0.0004(6) 0.0110(7) -0.0016(7) C1 0.0142(9) 0.0232(11) 0.0210(10) 0.0062(8) 0.0029(7) 0.0002(8) C2 0.0144(9) 0.0176(10) 0.0167(9) 0.0006(7) 0.0018(7) 0.0004(7) C3 0.0164(9) 0.0152(9) 0.0147(9) 0.0021(7) 0.0043(7) 0.0039(7) C4 0.0240(10) 0.0165(10) 0.0182(9) -0.0012(8) 0.0059(8) 0.0029(8) C5 0.0259(11) 0.0274(11) 0.0153(9) -0.0008(8) 0.0072(8) 0.0078(9) C6 0.0147(9) 0.0261(11) 0.0242(10) -0.0097(8) 0.0023(8) -0.0004(8) C7 0.0132(9) 0.0192(10) 0.0179(9) -0.0019(7) 0.0025(7) -0.0013(7) C8 0.0149(9) 0.0180(9) 0.0132(9) -0.0014(7) 0.0040(7) -0.0028(7) C9 0.0318(11) 0.0212(10) 0.0170(10) 0.0008(8) 0.0071(8) -0.0067(9) C10 0.0323(12) 0.0361(13) 0.0188(10) -0.0022(9) 0.0105(9) -0.0149(10) C11 0.0100(8) 0.0107(8) 0.0112(8) 0.0000(6) 0.0016(6) -0.0005(6) C12 0.0121(8) 0.0117(8) 0.0090(8) 0.0013(6) 0.0026(6) -0.0005(6) C13 0.0134(8) 0.0122(9) 0.0097(8) -0.0010(6) 0.0025(6) 0.0000(7) C14 0.0106(8) 0.0111(8) 0.0110(8) -0.0006(6) 0.0018(6) -0.0008(6) C15 0.0103(8) 0.0131(9) 0.0103(8) 0.0018(6) 0.0023(6) -0.0013(6) C16 0.0136(8) 0.0122(9) 0.0103(8) -0.0022(7) 0.0033(6) -0.0009(7) C17 0.0125(8) 0.0111(8) 0.0133(8) -0.0012(7) 0.0055(7) -0.0020(6) C18 0.0156(9) 0.0100(8) 0.0142(9) 0.0024(7) 0.0063(7) 0.0030(7) C19 0.0155(9) 0.0121(9) 0.0111(8) -0.0013(7) 0.0072(7) -0.0030(7) C20 0.0111(8) 0.0138(9) 0.0149(9) 0.0023(7) 0.0055(7) 0.0003(7) _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 O4 1.9510(13) . ? Zn1 O7 1.9675(13) 4_566 ? Zn1 O5 1.9683(13) 2_746 ? Zn1 O2 1.9816(13) 3_756 ? O1 C17 1.232(2) . ? O2 C17 1.289(2) . ? O2 Zn1 1.9816(13) 3_756 ? O3 C18 1.243(2) . ? O4 C18 1.270(2) . ? O5 C19 1.276(2) . ? O5 Zn1 1.9683(13) 2_756 ? O6 C19 1.235(2) . ? O7 C20 1.270(2) . ? O7 Zn1 1.9675(13) 4_665 ? O8 C20 1.239(2) . ? N1 C5 1.341(3) . ? N1 C1 1.345(3) . ? N2 C10 1.340(3) . ? N2 C6 1.347(3) . ? N3 C3 1.375(2) . ? N3 C8 1.380(2) . ? C1 C2 1.370(3) . ? C2 C3 1.400(3) . ? C3 C4 1.407(3) . ? C4 C5 1.366(3) . ? C6 C7 1.366(3) . ? C7 C8 1.398(3) . ? C8 C9 1.403(3) . ? C9 C10 1.368(3) . ? C11 C16 1.393(2) . ? C11 C12 1.399(2) . ? C11 C17 1.517(2) . ? C12 C13 1.397(2) . ? C12 C18 1.508(2) . ? C13 C14 1.394(2) . ? C14 C15 1.401(2) . ? C14 C19 1.522(2) . ? C15 C16 1.396(2) . ? C15 C20 1.506(2) . ? 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 O4 Zn1 O7 131.01(6) . 4_566 ? O4 Zn1 O5 112.07(6) . 2_746 ? O7 Zn1 O5 101.64(5) 4_566 2_746 ? O4 Zn1 O2 106.08(6) . 3_756 ? O7 Zn1 O2 104.51(6) 4_566 3_756 ? O5 Zn1 O2 95.98(6) 2_746 3_756 ? C17 O2 Zn1 136.29(12) . 3_756 ? C18 O4 Zn1 114.56(11) . . ? C19 O5 Zn1 134.29(12) . 2_756 ? C20 O7 Zn1 112.46(11) . 4_665 ? C5 N1 C1 121.85(18) . . ? C10 N2 C6 121.59(18) . . ? C3 N3 C8 130.15(17) . . ? N1 C1 C2 120.64(19) . . ? C1 C2 C3 119.26(19) . . ? N3 C3 C2 124.68(18) . . ? N3 C3 C4 117.03(18) . . ? C2 C3 C4 118.27(17) . . ? C5 C4 C3 119.89(19) . . ? N1 C5 C4 120.07(19) . . ? N2 C6 C7 120.6(2) . . ? C6 C7 C8 119.30(19) . . ? N3 C8 C7 124.35(17) . . ? N3 C8 C9 117.05(18) . . ? C7 C8 C9 118.53(18) . . ? C10 C9 C8 119.6(2) . . ? N2 C10 C9 120.3(2) . . ? C16 C11 C12 118.50(16) . . ? C16 C11 C17 117.59(15) . . ? C12 C11 C17 123.91(15) . . ? C13 C12 C11 119.22(16) . . ? C13 C12 C18 116.57(15) . . ? C11 C12 C18 124.13(16) . . ? C14 C13 C12 122.27(16) . . ? C13 C14 C15 118.47(16) . . ? C13 C14 C19 115.76(15) . . ? C15 C14 C19 125.76(16) . . ? C16 C15 C14 119.18(16) . . ? C16 C15 C20 117.34(16) . . ? C14 C15 C20 123.47(16) . . ? C11 C16 C15 122.35(16) . . ? O1 C17 O2 125.95(17) . . ? O1 C17 C11 120.81(16) . . ? O2 C17 C11 113.08(15) . . ? O3 C18 O4 124.44(17) . . ? O3 C18 C12 118.14(16) . . ? O4 C18 C12 117.41(15) . . ? O6 C19 O5 126.22(17) . . ? O6 C19 C14 120.74(16) . . ? O5 C19 C14 112.72(16) . . ? O8 C20 O7 123.69(17) . . ? O8 C20 C15 118.72(16) . . ? O7 C20 C15 117.58(16) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.342 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.077