# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yongqin, Wei' _publ_contact_author_email wyq507@fjirsm.ac.cn loop_ _publ_author_name 'Wei Yongqin' 'Wu Kechen' data_4a _database_code_depnum_ccdc_archive 'CCDC 772274' #TrackingRef 'left-handed.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H13 Cl N4 O3 Zn' _chemical_formula_weight 458.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.287(3) _cell_length_b 7.0017(19) _cell_length_c 13.168(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.941(4) _cell_angle_gamma 90.00 _cell_volume 855.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2565 _cell_measurement_theta_min 3.0956 _cell_measurement_theta_max 27.4565 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.099 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_min 0.062 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.625 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.904 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _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 6538 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3566 _reflns_number_gt 3215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _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^)+(0.0626P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.065(14) _refine_ls_number_reflns 3566 _refine_ls_number_parameters 270 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.48372(4) 0.39583(7) 0.79668(3) 0.02228(12) Uani 1 1 d . . . Cl1 Cl 0.44592(12) 0.08005(15) 0.82965(8) 0.0354(2) Uani 1 1 d . . . O1 O 0.7057(3) 0.0426(4) 0.1865(2) 0.0321(7) Uani 1 1 d . . . O2 O 0.6886(3) 0.1931(4) 0.0380(2) 0.0323(6) Uani 1 1 d . . . O3 O 0.5541(3) 0.4946(5) 0.9308(2) 0.0322(7) Uani 1 1 d D . . N1 N 0.7026(3) 0.3846(6) 0.7353(2) 0.0226(6) Uani 1 1 d . . . N2 N 0.4577(3) 0.4223(5) 0.6371(2) 0.0217(6) Uani 1 1 d . . . N3 N 0.9530(3) 0.3074(5) 0.4016(2) 0.0240(7) Uani 1 1 d . . . N4 N 0.7505(3) 0.3664(5) 0.3198(2) 0.0230(7) Uani 1 1 d . . . H4A H 0.6911 0.3841 0.2692 0.028 Uiso 1 1 calc R . . C1 C 0.8203(4) 0.3536(6) 0.7871(3) 0.0282(10) Uani 1 1 d . . . H1A H 0.8195 0.3590 0.8576 0.034 Uiso 1 1 calc R . . C2 C 0.9517(4) 0.3114(6) 0.7394(3) 0.0295(8) Uani 1 1 d . . . H2A H 1.0332 0.2872 0.7804 0.035 Uiso 1 1 calc R . . C3 C 0.9644(4) 0.3047(6) 0.6352(3) 0.0253(8) Uani 1 1 d . . . H3C H 1.0509 0.2745 0.6055 0.030 Uiso 1 1 calc R . . C4 C 0.8437(4) 0.3445(5) 0.5791(3) 0.0216(8) Uani 1 1 d . . . C5 C 0.8428(4) 0.3453(5) 0.4706(3) 0.0223(8) Uani 1 1 d . . . C6 C 0.7151(3) 0.3817(7) 0.4209(2) 0.0217(7) Uani 1 1 d . . . C7 C 0.5779(3) 0.4031(7) 0.4723(2) 0.0210(6) Uani 1 1 d . . . C8 C 0.4422(3) 0.4115(7) 0.4261(3) 0.0236(7) Uani 1 1 d . . . H8A H 0.4318 0.4111 0.3556 0.028 Uiso 1 1 calc R . . C9 C 0.3193(4) 0.4206(6) 0.4863(3) 0.0270(8) Uani 1 1 d . . . H9A H 0.2282 0.4202 0.4547 0.032 Uiso 1 1 calc R . . C10 C 0.3313(4) 0.4300(6) 0.5915(3) 0.0243(9) Uani 1 1 d . . . H10A H 0.2491 0.4417 0.6294 0.029 Uiso 1 1 calc R . . C11 C 0.7132(3) 0.3809(7) 0.6325(2) 0.0207(6) Uani 1 1 d . . . C12 C 0.5792(3) 0.4041(7) 0.5791(2) 0.0202(6) Uani 1 1 d . . . C13 C 0.8922(4) 0.3193(5) 0.3115(3) 0.0228(8) Uani 1 1 d . . . C14 C 0.9701(4) 0.2905(6) 0.2126(3) 0.0213(7) Uani 1 1 d . . . C15 C 1.1177(4) 0.3419(5) 0.2100(3) 0.0259(9) Uani 1 1 d . . . H15A H 1.1622 0.3921 0.2684 0.031 Uiso 1 1 calc R . . C16 C 1.2013(4) 0.3197(6) 0.1213(3) 0.0299(9) Uani 1 1 d . . . H16A H 1.2977 0.3559 0.1232 0.036 Uiso 1 1 calc R . . C17 C 1.1414(4) 0.2469(6) 0.0353(3) 0.0301(9) Uani 1 1 d . . . H17A H 1.1951 0.2281 -0.0222 0.036 Uiso 1 1 calc R . . C18 C 0.9962(4) 0.2009(6) 0.0361(3) 0.0266(8) Uani 1 1 d . . . H18A H 0.9527 0.1544 -0.0235 0.032 Uiso 1 1 calc R . . C19 C 0.9088(4) 0.2210(6) 0.1238(3) 0.0214(7) Uani 1 1 d . . . C20 C 0.7537(4) 0.1499(5) 0.1153(3) 0.0225(7) Uani 1 1 d . . . H1 H 0.585(5) 0.406(6) 0.972(3) 0.056(15) Uiso 1 1 d D . . H2 H 0.488(4) 0.549(6) 0.963(3) 0.032(13) 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 0.02063(18) 0.0303(2) 0.01580(19) -0.0013(2) -0.00061(13) 0.0009(2) Cl1 0.0464(5) 0.0333(5) 0.0261(5) 0.0014(4) -0.0076(4) -0.0118(4) O1 0.0275(13) 0.049(2) 0.0194(14) 0.0077(12) -0.0026(11) -0.0146(13) O2 0.0316(15) 0.0400(17) 0.0248(15) 0.0067(12) -0.0066(12) -0.0030(13) O3 0.0318(15) 0.0454(17) 0.0191(15) -0.0046(13) -0.0040(12) 0.0007(13) N1 0.0219(12) 0.0294(15) 0.0162(13) -0.0042(16) -0.0023(10) -0.0012(16) N2 0.0193(12) 0.0278(19) 0.0179(13) -0.0023(14) 0.0005(10) 0.0020(13) N3 0.0164(14) 0.0347(17) 0.0208(16) -0.0010(13) -0.0007(12) 0.0005(13) N4 0.0192(12) 0.035(2) 0.0145(13) 0.0005(13) -0.0021(10) 0.0019(13) C1 0.0258(16) 0.042(3) 0.0167(17) -0.0018(15) -0.0059(13) -0.0002(16) C2 0.0272(19) 0.036(2) 0.025(2) -0.0006(17) -0.0098(16) -0.0006(17) C3 0.0153(16) 0.037(2) 0.0240(19) -0.0018(16) -0.0017(14) -0.0023(15) C4 0.0199(16) 0.025(2) 0.0199(17) -0.0001(13) -0.0027(13) -0.0040(13) C5 0.0193(15) 0.028(2) 0.0196(18) -0.0011(13) -0.0006(13) -0.0007(13) C6 0.0196(14) 0.0289(18) 0.0164(15) -0.0023(18) 0.0001(12) 0.0047(18) C7 0.0224(14) 0.0228(17) 0.0179(15) 0.0011(18) 0.0001(11) 0.0022(19) C8 0.0234(15) 0.030(2) 0.0176(15) 0.0015(18) -0.0028(12) 0.0006(18) C9 0.0218(15) 0.036(2) 0.0234(17) -0.0025(18) -0.0033(13) 0.0019(18) C10 0.0167(14) 0.036(3) 0.0202(17) -0.0036(15) 0.0007(12) 0.0011(15) C11 0.0200(14) 0.0234(17) 0.0184(15) -0.0015(17) -0.0010(11) -0.0021(17) C12 0.0193(13) 0.0214(16) 0.0199(15) -0.0016(19) -0.0019(11) 0.0001(18) C13 0.0203(17) 0.0291(18) 0.0190(18) 0.0014(14) -0.0004(14) 0.0006(14) C14 0.0206(17) 0.0233(19) 0.0202(18) 0.0003(14) 0.0036(14) 0.0008(14) C15 0.0199(16) 0.031(2) 0.027(2) 0.0001(14) -0.0014(14) -0.0028(13) C16 0.0184(17) 0.036(2) 0.036(2) 0.0004(17) 0.0069(16) -0.0014(15) C17 0.032(2) 0.035(2) 0.024(2) 0.0025(17) 0.0118(16) 0.0031(17) C18 0.032(2) 0.030(2) 0.0183(19) -0.0001(15) 0.0032(15) 0.0012(16) C19 0.0202(17) 0.0252(18) 0.0187(18) 0.0027(14) 0.0020(14) 0.0006(14) C20 0.0241(17) 0.0285(19) 0.0149(17) -0.0043(14) 0.0011(14) -0.0010(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.987(3) . ? Zn1 O1 2.056(3) 2_656 ? Zn1 N2 2.116(3) . ? Zn1 N1 2.214(3) . ? Zn1 Cl1 2.2826(13) . ? O1 C20 1.292(5) . ? O1 Zn1 2.056(3) 2_646 ? O2 C20 1.205(4) . ? O3 H1 0.868(19) . ? O3 H2 0.853(18) . ? N1 C1 1.287(4) . ? N1 C11 1.361(4) . ? N2 C10 1.302(4) . ? N2 C12 1.389(4) . ? N3 C13 1.299(5) . ? N3 C5 1.417(5) . ? N4 C13 1.365(4) . ? N4 C6 1.385(4) . ? N4 H4A 0.8600 . ? C1 C2 1.422(6) . ? C1 H1A 0.9300 . ? C2 C3 1.382(6) . ? C2 H2A 0.9300 . ? C3 C4 1.350(5) . ? C3 H3C 0.9300 . ? C4 C5 1.428(5) . ? C4 C11 1.444(5) . ? C5 C6 1.360(5) . ? C6 C7 1.471(4) . ? C7 C8 1.381(4) . ? C7 C12 1.406(4) . ? C8 C9 1.413(5) . ? C8 H8A 0.9300 . ? C9 C10 1.387(5) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.418(4) . ? C13 C14 1.524(5) . ? C14 C19 1.373(5) . ? C14 C15 1.419(5) . ? C15 C16 1.433(6) . ? C15 H15A 0.9300 . ? C16 C17 1.345(6) . ? C16 H16A 0.9300 . ? C17 C18 1.387(6) . ? C17 H17A 0.9300 . ? C18 C19 1.440(5) . ? C18 H18A 0.9300 . ? C19 C20 1.524(5) . ? 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 O1 89.25(12) . 2_656 ? O3 Zn1 N2 151.15(12) . . ? O1 Zn1 N2 89.68(11) 2_656 . ? O3 Zn1 N1 93.36(12) . . ? O1 Zn1 N1 148.94(13) 2_656 . ? N2 Zn1 N1 73.48(10) . . ? O3 Zn1 Cl1 102.47(10) . . ? O1 Zn1 Cl1 109.03(10) 2_656 . ? N2 Zn1 Cl1 105.11(10) . . ? N1 Zn1 Cl1 100.61(11) . . ? C20 O1 Zn1 133.4(2) . 2_646 ? Zn1 O3 H1 114(4) . . ? Zn1 O3 H2 112(3) . . ? H1 O3 H2 104(3) . . ? C1 N1 C11 115.8(3) . . ? C1 N1 Zn1 125.9(3) . . ? C11 N1 Zn1 117.5(2) . . ? C10 N2 C12 119.2(3) . . ? C10 N2 Zn1 122.2(2) . . ? C12 N2 Zn1 118.1(2) . . ? C13 N3 C5 105.9(3) . . ? C13 N4 C6 110.9(3) . . ? C13 N4 H4A 124.5 . . ? C6 N4 H4A 124.5 . . ? N1 C1 C2 121.8(4) . . ? N1 C1 H1A 119.1 . . ? C2 C1 H1A 119.1 . . ? C3 C2 C1 123.3(3) . . ? C3 C2 H2A 118.4 . . ? C1 C2 H2A 118.4 . . ? C4 C3 C2 116.1(4) . . ? C4 C3 H3C 122.0 . . ? C2 C3 H3C 122.0 . . ? C3 C4 C5 121.6(3) . . ? C3 C4 C11 117.7(3) . . ? C5 C4 C11 120.7(3) . . ? C6 C5 N3 111.3(3) . . ? C6 C5 C4 117.3(3) . . ? N3 C5 C4 131.4(3) . . ? C5 C6 N4 102.5(3) . . ? C5 C6 C7 123.5(3) . . ? N4 C6 C7 133.4(3) . . ? C8 C7 C12 114.7(3) . . ? C8 C7 C6 126.4(3) . . ? C12 C7 C6 118.8(3) . . ? C7 C8 C9 119.8(3) . . ? C7 C8 H8A 120.1 . . ? C9 C8 H8A 120.1 . . ? C10 C9 C8 121.6(3) . . ? C10 C9 H9A 119.2 . . ? C8 C9 H9A 119.2 . . ? N2 C10 C9 119.9(3) . . ? N2 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? N1 C11 C12 113.5(3) . . ? N1 C11 C4 125.3(3) . . ? C12 C11 C4 121.0(3) . . ? N2 C12 C7 124.8(3) . . ? N2 C12 C11 117.0(3) . . ? C7 C12 C11 118.3(3) . . ? N3 C13 N4 109.4(3) . . ? N3 C13 C14 124.6(3) . . ? N4 C13 C14 126.0(3) . . ? C19 C14 C15 116.3(3) . . ? C19 C14 C13 125.4(3) . . ? C15 C14 C13 118.3(3) . . ? C14 C15 C16 122.9(4) . . ? C14 C15 H15A 118.6 . . ? C16 C15 H15A 118.6 . . ? C17 C16 C15 120.5(4) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 117.1(4) . . ? C16 C17 H17A 121.4 . . ? C18 C17 H17A 121.4 . . ? C17 C18 C19 123.9(4) . . ? C17 C18 H18A 118.0 . . ? C19 C18 H18A 118.0 . . ? C14 C19 C18 119.2(3) . . ? C14 C19 C20 122.8(3) . . ? C18 C19 C20 117.8(3) . . ? O2 C20 O1 125.7(4) . . ? O2 C20 C19 115.2(3) . . ? O1 C20 C19 119.0(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 O3 Zn1 N1 C1 30.8(4) . . . . ? O1 Zn1 N1 C1 124.9(4) 2_656 . . . ? N2 Zn1 N1 C1 -175.3(4) . . . . ? Cl1 Zn1 N1 C1 -72.6(4) . . . . ? O3 Zn1 N1 C11 -159.9(4) . . . . ? O1 Zn1 N1 C11 -65.8(4) 2_656 . . . ? N2 Zn1 N1 C11 -6.0(3) . . . . ? Cl1 Zn1 N1 C11 96.8(3) . . . . ? O3 Zn1 N2 C10 -118.3(3) . . . . ? O1 Zn1 N2 C10 -30.4(3) 2_656 . . . ? N1 Zn1 N2 C10 176.0(3) . . . . ? Cl1 Zn1 N2 C10 79.2(3) . . . . ? O3 Zn1 N2 C12 70.7(4) . . . . ? O1 Zn1 N2 C12 158.6(3) 2_656 . . . ? N1 Zn1 N2 C12 5.0(3) . . . . ? Cl1 Zn1 N2 C12 -91.8(3) . . . . ? C11 N1 C1 C2 -2.2(6) . . . . ? Zn1 N1 C1 C2 167.3(3) . . . . ? N1 C1 C2 C3 1.5(7) . . . . ? C1 C2 C3 C4 1.2(6) . . . . ? C2 C3 C4 C5 179.0(3) . . . . ? C2 C3 C4 C11 -2.8(5) . . . . ? C13 N3 C5 C6 -0.5(4) . . . . ? C13 N3 C5 C4 177.0(4) . . . . ? C3 C4 C5 C6 178.2(4) . . . . ? C11 C4 C5 C6 0.1(5) . . . . ? C3 C4 C5 N3 0.8(6) . . . . ? C11 C4 C5 N3 -177.3(4) . . . . ? N3 C5 C6 N4 -0.4(5) . . . . ? C4 C5 C6 N4 -178.3(3) . . . . ? N3 C5 C6 C7 172.4(4) . . . . ? C4 C5 C6 C7 -5.5(6) . . . . ? C13 N4 C6 C5 1.1(5) . . . . ? C13 N4 C6 C7 -170.6(5) . . . . ? C5 C6 C7 C8 -169.6(5) . . . . ? N4 C6 C7 C8 0.7(9) . . . . ? C5 C6 C7 C12 6.2(7) . . . . ? N4 C6 C7 C12 176.5(5) . . . . ? C12 C7 C8 C9 0.1(7) . . . . ? C6 C7 C8 C9 176.1(5) . . . . ? C7 C8 C9 C10 2.9(7) . . . . ? C12 N2 C10 C9 -0.2(6) . . . . ? Zn1 N2 C10 C9 -171.1(3) . . . . ? C8 C9 C10 N2 -3.0(6) . . . . ? C1 N1 C11 C12 176.3(4) . . . . ? Zn1 N1 C11 C12 5.9(5) . . . . ? C1 N1 C11 C4 0.4(7) . . . . ? Zn1 N1 C11 C4 -170.0(3) . . . . ? C3 C4 C11 N1 2.3(6) . . . . ? C5 C4 C11 N1 -179.6(4) . . . . ? C3 C4 C11 C12 -173.4(4) . . . . ? C5 C4 C11 C12 4.8(6) . . . . ? C10 N2 C12 C7 3.5(7) . . . . ? Zn1 N2 C12 C7 174.8(4) . . . . ? C10 N2 C12 C11 -175.1(4) . . . . ? Zn1 N2 C12 C11 -3.8(6) . . . . ? C8 C7 C12 N2 -3.4(7) . . . . ? C6 C7 C12 N2 -179.7(5) . . . . ? C8 C7 C12 C11 175.2(4) . . . . ? C6 C7 C12 C11 -1.1(7) . . . . ? N1 C11 C12 N2 -1.5(6) . . . . ? C4 C11 C12 N2 174.6(4) . . . . ? N1 C11 C12 C7 179.8(5) . . . . ? C4 C11 C12 C7 -4.0(7) . . . . ? C5 N3 C13 N4 1.2(4) . . . . ? C5 N3 C13 C14 179.5(3) . . . . ? C6 N4 C13 N3 -1.5(5) . . . . ? C6 N4 C13 C14 -179.8(4) . . . . ? N3 C13 C14 C19 150.1(4) . . . . ? N4 C13 C14 C19 -31.9(6) . . . . ? N3 C13 C14 C15 -31.1(6) . . . . ? N4 C13 C14 C15 147.0(4) . . . . ? C19 C14 C15 C16 -1.4(6) . . . . ? C13 C14 C15 C16 179.6(4) . . . . ? C14 C15 C16 C17 -0.3(6) . . . . ? C15 C16 C17 C18 1.9(6) . . . . ? C16 C17 C18 C19 -2.1(7) . . . . ? C15 C14 C19 C18 1.3(6) . . . . ? C13 C14 C19 C18 -179.8(3) . . . . ? C15 C14 C19 C20 176.8(3) . . . . ? C13 C14 C19 C20 -4.3(6) . . . . ? C17 C18 C19 C14 0.4(6) . . . . ? C17 C18 C19 C20 -175.3(4) . . . . ? Zn1 O1 C20 O2 2.1(6) 2_646 . . . ? Zn1 O1 C20 C19 -173.8(3) 2_646 . . . ? C14 C19 C20 O2 140.0(4) . . . . ? C18 C19 C20 O2 -44.5(5) . . . . ? C14 C19 C20 O1 -43.7(6) . . . . ? C18 C19 C20 O1 131.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.414 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.127 # Attachment 'right-handed.CIF' data_4 _database_code_depnum_ccdc_archive 'CCDC 789384' #TrackingRef 'right-handed.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H13 Cl N4 O3 Zn' _chemical_formula_weight 458.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.291(5) _cell_length_b 7.006(3) _cell_length_c 13.182(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.935(7) _cell_angle_gamma 90.00 _cell_volume 857.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2570 _cell_measurement_theta_min 3.0924 _cell_measurement_theta_max 27.4603 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.104 _exptl_crystal_size_mid 0.073 _exptl_crystal_size_min 0.042 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.775 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.622 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_T_max 0.934 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _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 6621 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3327 _reflns_number_gt 2897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _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^)+(0.0807P)^2^+0.0368P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.020(17) _refine_ls_number_reflns 3327 _refine_ls_number_parameters 270 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 0.01630(4) 0.37074(9) 0.20336(3) 0.02258(15) Uani 1 1 d . . . Cl1 Cl 0.05406(14) 0.6865(2) 0.17054(9) 0.0354(3) Uani 1 1 d . . . C12 C -0.0790(4) 0.3621(9) 0.4206(3) 0.0206(8) Uani 1 1 d . . . N4 N -0.2501(3) 0.3995(7) 0.6805(2) 0.0230(9) Uani 1 1 d . . . H4A H -0.1905 0.3826 0.7310 0.028 Uiso 1 1 calc R . . C7 C -0.0779(4) 0.3622(9) 0.5276(3) 0.0208(8) Uani 1 1 d . . . C8 C 0.0576(4) 0.3554(9) 0.5738(3) 0.0251(9) Uani 1 1 d . . . H8A H 0.0677 0.3570 0.6442 0.030 Uiso 1 1 calc R . . N2 N 0.0424(4) 0.3439(6) 0.3631(2) 0.0227(8) Uani 1 1 d . . . C11 C -0.2132(4) 0.3852(8) 0.3676(3) 0.0209(8) Uani 1 1 d . . . C9 C 0.1806(4) 0.3460(8) 0.5142(3) 0.0273(11) Uani 1 1 d . . . H9A H 0.2715 0.3463 0.5460 0.033 Uiso 1 1 calc R . . C15 C -0.4093(4) 0.5460(7) 0.8762(3) 0.0201(9) Uani 1 1 d . . . C6 C -0.2148(4) 0.3837(9) 0.5788(3) 0.0208(8) Uani 1 1 d . . . C16 C -0.4963(5) 0.5650(8) 0.9638(3) 0.0266(10) Uani 1 1 d . . . H16A H -0.4527 0.6108 1.0235 0.032 Uiso 1 1 calc R . . C18 C -0.7009(5) 0.4467(8) 0.8784(4) 0.0294(10) Uani 1 1 d . . . H18A H -0.7974 0.4109 0.8765 0.035 Uiso 1 1 calc R . . C4 C -0.3429(4) 0.4213(6) 0.4209(3) 0.0209(10) Uani 1 1 d . . . C14 C -0.4712(5) 0.4743(7) 0.7877(3) 0.0222(9) Uani 1 1 d . . . C3 C -0.4635(5) 0.4616(7) 0.3639(3) 0.0261(10) Uani 1 1 d . . . H3A H -0.5498 0.4926 0.3936 0.031 Uiso 1 1 calc R . . C2 C -0.4520(5) 0.4543(8) 0.2602(3) 0.0297(10) Uani 1 1 d . . . H2A H -0.5337 0.4773 0.2192 0.036 Uiso 1 1 calc R . . C13 C -0.3931(4) 0.4457(7) 0.6889(3) 0.0222(9) Uani 1 1 d . . . C10 C 0.1685(4) 0.3362(7) 0.4086(3) 0.0254(11) Uani 1 1 d . . . H10A H 0.2506 0.3243 0.3707 0.030 Uiso 1 1 calc R . . C19 C -0.6177(4) 0.4244(7) 0.7902(3) 0.0259(11) Uani 1 1 d . . . H19A H -0.6623 0.3748 0.7317 0.031 Uiso 1 1 calc R . . C1 C -0.3205(5) 0.4132(7) 0.2134(3) 0.0286(12) Uani 1 1 d . . . H1A H -0.3195 0.4087 0.1429 0.034 Uiso 1 1 calc R . . C17 C -0.6406(5) 0.5193(8) 0.9646(4) 0.0300(11) Uani 1 1 d . . . H17A H -0.6941 0.5378 1.0221 0.036 Uiso 1 1 calc R . . N1 N -0.2025(3) 0.3820(7) 0.2644(2) 0.0226(7) Uani 1 1 d . . . O2 O -0.1892(3) 0.5728(5) 0.9618(2) 0.0317(8) Uani 1 1 d . . . N3 N -0.4524(4) 0.4586(6) 0.5987(3) 0.0248(8) Uani 1 1 d . . . O3 O -0.0536(4) 0.2720(6) 0.0693(2) 0.0330(8) Uani 1 1 d D . . C20 C -0.2546(5) 0.6170(7) 0.8847(3) 0.0226(9) Uani 1 1 d . . . C5 C -0.3424(4) 0.4208(7) 0.5294(3) 0.0222(10) Uani 1 1 d . . . O1 O -0.2059(3) 0.7236(6) 0.8133(2) 0.0326(9) Uani 1 1 d . . . H1 H -0.094(7) 0.361(9) 0.034(5) 0.09(3) Uiso 1 1 d D . . H2 H 0.010(5) 0.221(8) 0.034(4) 0.048(19) 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 0.0204(2) 0.0309(3) 0.0163(2) -0.0013(3) -0.00099(15) 0.0011(3) Cl1 0.0458(6) 0.0334(7) 0.0264(5) 0.0019(5) -0.0078(5) -0.0117(5) C12 0.0183(16) 0.024(2) 0.0198(16) 0.000(2) 0.0003(13) 0.001(2) N4 0.0188(14) 0.035(3) 0.0152(14) -0.0001(17) -0.0013(11) 0.0007(16) C7 0.0201(16) 0.022(2) 0.0206(16) -0.001(2) 0.0000(13) 0.002(2) C8 0.0209(17) 0.036(3) 0.0181(15) 0.000(2) -0.0022(13) 0.001(2) N2 0.0198(15) 0.028(2) 0.0201(14) -0.0058(17) 0.0019(12) 0.0015(17) C11 0.0189(16) 0.023(2) 0.0203(16) 0.000(2) -0.0045(13) -0.001(2) C9 0.0191(17) 0.038(3) 0.0248(18) -0.003(2) -0.0045(14) 0.001(2) C15 0.020(2) 0.021(2) 0.0188(19) 0.0020(17) 0.0024(16) 0.0007(17) C6 0.0202(16) 0.026(2) 0.0166(15) -0.004(2) 0.0000(13) 0.004(2) C16 0.029(2) 0.029(3) 0.0222(19) 0.0007(19) 0.0002(17) -0.001(2) C18 0.016(2) 0.032(3) 0.040(3) -0.001(2) 0.0046(18) -0.0012(18) C4 0.0196(18) 0.026(3) 0.0169(17) -0.0002(16) -0.0020(14) -0.0028(16) C14 0.021(2) 0.026(3) 0.0196(19) -0.0002(18) 0.0028(16) -0.0008(18) C3 0.0153(19) 0.037(3) 0.026(2) 0.000(2) -0.0030(16) -0.0040(19) C2 0.025(2) 0.038(3) 0.025(2) 0.000(2) -0.0093(18) 0.001(2) C13 0.020(2) 0.027(2) 0.0190(19) -0.0014(17) -0.0010(16) 0.0006(17) C10 0.0170(17) 0.037(3) 0.0217(18) -0.004(2) -0.0001(14) 0.0024(18) C19 0.0198(19) 0.032(3) 0.026(2) -0.0027(18) 0.0001(16) 0.0007(16) C1 0.0238(19) 0.043(4) 0.0184(17) -0.001(2) -0.0067(15) -0.0011(19) C17 0.032(3) 0.035(3) 0.024(2) 0.006(2) 0.0115(19) 0.002(2) N1 0.0221(14) 0.027(2) 0.0181(13) -0.005(2) -0.0031(11) 0.0004(19) O2 0.0309(17) 0.039(2) 0.0244(15) 0.0074(16) -0.0074(13) -0.0027(15) N3 0.0176(17) 0.038(2) 0.0190(16) -0.0013(16) -0.0013(13) -0.0001(16) O3 0.0301(18) 0.047(2) 0.0215(15) -0.0050(16) -0.0038(14) 0.0021(16) C20 0.025(2) 0.025(2) 0.0179(19) -0.0032(18) 0.0008(16) -0.0019(17) C5 0.0193(18) 0.030(3) 0.0176(17) -0.0001(16) -0.0003(15) -0.0023(15) O1 0.0268(16) 0.050(3) 0.0204(14) 0.0079(16) -0.0039(13) -0.0152(16) _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 1.987(3) . ? Zn1 O1 2.059(3) 2_546 ? Zn1 N2 2.120(3) . ? Zn1 N1 2.213(3) . ? Zn1 Cl1 2.2830(18) . ? C12 N2 1.386(5) . ? C12 C7 1.410(5) . ? C12 C11 1.418(5) . ? N4 C13 1.376(5) . ? N4 C6 1.395(5) . ? N4 H4A 0.8600 . ? C7 C8 1.380(5) . ? C7 C6 1.468(5) . ? C8 C9 1.410(6) . ? C8 H8A 0.9300 . ? N2 C10 1.299(5) . ? C11 N1 1.367(5) . ? C11 C4 1.438(6) . ? C9 C10 1.395(5) . ? C9 H9A 0.9300 . ? C15 C14 1.378(6) . ? C15 C16 1.438(6) . ? C15 C20 1.521(6) . ? C6 C5 1.357(5) . ? C16 C17 1.378(7) . ? C16 H16A 0.9300 . ? C18 C17 1.349(7) . ? C18 C19 1.427(6) . ? C18 H18A 0.9300 . ? C4 C3 1.357(6) . ? C4 C5 1.430(5) . ? C14 C19 1.407(6) . ? C14 C13 1.525(6) . ? C3 C2 1.377(6) . ? C3 H3A 0.9300 . ? C2 C1 1.417(7) . ? C2 H2A 0.9300 . ? C13 N3 1.297(5) . ? C10 H10A 0.9300 . ? C19 H19A 0.9300 . ? C1 N1 1.285(5) . ? C1 H1A 0.9300 . ? C17 H17A 0.9300 . ? O2 C20 1.207(5) . ? N3 C5 1.419(5) . ? O3 H1 0.86(2) . ? O3 H2 0.837(19) . ? C20 O1 1.294(5) . ? O1 Zn1 2.059(3) 2_556 ? 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 O1 89.18(14) . 2_546 ? O3 Zn1 N2 151.14(16) . . ? O1 Zn1 N2 89.54(13) 2_546 . ? O3 Zn1 N1 93.41(13) . . ? O1 Zn1 N1 148.92(16) 2_546 . ? N2 Zn1 N1 73.59(12) . . ? O3 Zn1 Cl1 102.50(13) . . ? O1 Zn1 Cl1 109.10(12) 2_546 . ? N2 Zn1 Cl1 105.14(13) . . ? N1 Zn1 Cl1 100.56(14) . . ? N2 C12 C7 124.7(3) . . ? N2 C12 C11 117.3(3) . . ? C7 C12 C11 118.0(3) . . ? C13 N4 C6 110.8(3) . . ? C13 N4 H4A 124.6 . . ? C6 N4 H4A 124.6 . . ? C8 C7 C12 114.6(3) . . ? C8 C7 C6 126.3(3) . . ? C12 C7 C6 118.9(3) . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? C10 N2 C12 119.3(3) . . ? C10 N2 Zn1 122.2(3) . . ? C12 N2 Zn1 117.9(2) . . ? N1 C11 C12 113.3(3) . . ? N1 C11 C4 125.4(3) . . ? C12 C11 C4 121.1(3) . . ? C10 C9 C8 121.2(4) . . ? C10 C9 H9A 119.4 . . ? C8 C9 H9A 119.4 . . ? C14 C15 C16 118.9(4) . . ? C14 C15 C20 123.2(4) . . ? C16 C15 C20 117.8(4) . . ? C5 C6 N4 102.5(3) . . ? C5 C6 C7 123.8(3) . . ? N4 C6 C7 133.2(3) . . ? C17 C16 C15 123.9(4) . . ? C17 C16 H16A 118.1 . . ? C15 C16 H16A 118.1 . . ? C17 C18 C19 120.4(4) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C3 C4 C5 121.9(4) . . ? C3 C4 C11 117.1(4) . . ? C5 C4 C11 120.9(3) . . ? C15 C14 C19 116.6(4) . . ? C15 C14 C13 125.0(4) . . ? C19 C14 C13 118.4(4) . . ? C4 C3 C2 116.9(4) . . ? C4 C3 H3A 121.6 . . ? C2 C3 H3A 121.6 . . ? C3 C2 C1 122.5(4) . . ? C3 C2 H2A 118.8 . . ? C1 C2 H2A 118.8 . . ? N3 C13 N4 108.9(4) . . ? N3 C13 C14 125.0(4) . . ? N4 C13 C14 126.1(4) . . ? N2 C10 C9 120.0(4) . . ? N2 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C14 C19 C18 122.9(4) . . ? C14 C19 H19A 118.5 . . ? C18 C19 H19A 118.5 . . ? N1 C1 C2 122.7(4) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? C18 C17 C16 117.3(4) . . ? C18 C17 H17A 121.4 . . ? C16 C17 H17A 121.4 . . ? C1 N1 C11 115.4(3) . . ? C1 N1 Zn1 126.4(3) . . ? C11 N1 Zn1 117.4(2) . . ? C13 N3 C5 106.5(3) . . ? Zn1 O3 H1 110(6) . . ? Zn1 O3 H2 115(4) . . ? H1 O3 H2 109(3) . . ? O2 C20 O1 125.5(4) . . ? O2 C20 C15 115.2(4) . . ? O1 C20 C15 119.2(4) . . ? C6 C5 N3 111.3(3) . . ? C6 C5 C4 116.9(4) . . ? N3 C5 C4 131.7(4) . . ? C20 O1 Zn1 133.4(3) . 2_556 ? 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 N2 C12 C7 C8 4.2(9) . . . . ? C11 C12 C7 C8 -174.8(6) . . . . ? N2 C12 C7 C6 179.7(6) . . . . ? C11 C12 C7 C6 0.8(9) . . . . ? C12 C7 C8 C9 -1.0(9) . . . . ? C6 C7 C8 C9 -176.1(6) . . . . ? C7 C12 N2 C10 -3.9(9) . . . . ? C11 C12 N2 C10 175.1(5) . . . . ? C7 C12 N2 Zn1 -175.0(5) . . . . ? C11 C12 N2 Zn1 4.0(7) . . . . ? O3 Zn1 N2 C10 118.0(4) . . . . ? O1 Zn1 N2 C10 30.5(4) 2_546 . . . ? N1 Zn1 N2 C10 -175.9(4) . . . . ? Cl1 Zn1 N2 C10 -79.1(4) . . . . ? O3 Zn1 N2 C12 -71.1(6) . . . . ? O1 Zn1 N2 C12 -158.6(4) 2_546 . . . ? N1 Zn1 N2 C12 -5.1(4) . . . . ? Cl1 Zn1 N2 C12 91.7(4) . . . . ? N2 C12 C11 N1 1.3(8) . . . . ? C7 C12 C11 N1 -179.7(6) . . . . ? N2 C12 C11 C4 -174.7(5) . . . . ? C7 C12 C11 C4 4.4(8) . . . . ? C7 C8 C9 C10 -2.4(9) . . . . ? C13 N4 C6 C5 -0.4(6) . . . . ? C13 N4 C6 C7 171.0(6) . . . . ? C8 C7 C6 C5 168.8(6) . . . . ? C12 C7 C6 C5 -6.2(9) . . . . ? C8 C7 C6 N4 -1.1(11) . . . . ? C12 C7 C6 N4 -176.1(6) . . . . ? C14 C15 C16 C17 -1.4(8) . . . . ? C20 C15 C16 C17 175.2(5) . . . . ? N1 C11 C4 C3 -2.2(8) . . . . ? C12 C11 C4 C3 173.2(5) . . . . ? N1 C11 C4 C5 179.8(5) . . . . ? C12 C11 C4 C5 -4.7(7) . . . . ? C16 C15 C14 C19 0.0(7) . . . . ? C20 C15 C14 C19 -176.5(4) . . . . ? C16 C15 C14 C13 -179.9(4) . . . . ? C20 C15 C14 C13 3.6(8) . . . . ? C5 C4 C3 C2 -178.8(5) . . . . ? C11 C4 C3 C2 3.2(7) . . . . ? C4 C3 C2 C1 -2.0(8) . . . . ? C6 N4 C13 N3 0.7(6) . . . . ? C6 N4 C13 C14 179.8(5) . . . . ? C15 C14 C13 N3 -148.8(5) . . . . ? C19 C14 C13 N3 31.2(7) . . . . ? C15 C14 C13 N4 32.2(8) . . . . ? C19 C14 C13 N4 -147.8(5) . . . . ? C12 N2 C10 C9 0.1(8) . . . . ? Zn1 N2 C10 C9 170.8(4) . . . . ? C8 C9 C10 N2 2.9(8) . . . . ? C15 C14 C19 C18 0.5(7) . . . . ? C13 C14 C19 C18 -179.6(4) . . . . ? C17 C18 C19 C14 0.4(8) . . . . ? C3 C2 C1 N1 -0.8(9) . . . . ? C19 C18 C17 C16 -1.7(8) . . . . ? C15 C16 C17 C18 2.3(8) . . . . ? C2 C1 N1 C11 2.0(8) . . . . ? C2 C1 N1 Zn1 -167.6(4) . . . . ? C12 C11 N1 C1 -176.3(5) . . . . ? C4 C11 N1 C1 -0.5(8) . . . . ? C12 C11 N1 Zn1 -5.7(6) . . . . ? C4 C11 N1 Zn1 170.0(4) . . . . ? O3 Zn1 N1 C1 -31.0(5) . . . . ? O1 Zn1 N1 C1 -125.0(4) 2_546 . . . ? N2 Zn1 N1 C1 175.3(5) . . . . ? Cl1 Zn1 N1 C1 72.4(5) . . . . ? O3 Zn1 N1 C11 159.7(4) . . . . ? O1 Zn1 N1 C11 65.6(5) 2_546 . . . ? N2 Zn1 N1 C11 5.9(4) . . . . ? Cl1 Zn1 N1 C11 -96.9(4) . . . . ? N4 C13 N3 C5 -0.6(5) . . . . ? C14 C13 N3 C5 -179.7(4) . . . . ? C14 C15 C20 O2 -138.9(5) . . . . ? C16 C15 C20 O2 44.6(6) . . . . ? C14 C15 C20 O1 44.0(7) . . . . ? C16 C15 C20 O1 -132.6(5) . . . . ? N4 C6 C5 N3 0.1(6) . . . . ? C7 C6 C5 N3 -172.4(5) . . . . ? N4 C6 C5 C4 178.3(4) . . . . ? C7 C6 C5 C4 5.8(8) . . . . ? C13 N3 C5 C6 0.3(6) . . . . ? C13 N3 C5 C4 -177.6(5) . . . . ? C3 C4 C5 C6 -178.3(5) . . . . ? C11 C4 C5 C6 -0.4(7) . . . . ? C3 C4 C5 N3 -0.5(8) . . . . ? C11 C4 C5 N3 177.3(5) . . . . ? O2 C20 O1 Zn1 -3.3(8) . . . 2_556 ? C15 C20 O1 Zn1 173.6(3) . . . 2_556 ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.421 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.132