# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a _database_code_depnum_ccdc_archive 'CCDC 912059' #TrackingRef 'Ac-6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H30 N4 O7 Zn' _chemical_formula_weight 479.83 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 9.4123(16) _cell_length_b 9.4994(7) _cell_length_c 13.1602(18) _cell_angle_alpha 74.96(2) _cell_angle_beta 83.55(3) _cell_angle_gamma 82.90(3) _cell_volume 1123.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3090 _cell_measurement_theta_min 2.4033 _cell_measurement_theta_max 27.4972 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.3000 _exptl_crystal_size_mid 0.2500 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 1.138 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9398 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Mercury70 (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12364 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5103 _reflns_number_gt 4402 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.1000P)^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 5103 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1613 _refine_ls_wR_factor_gt 0.1480 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.74352(3) 0.61279(3) 0.71619(3) 0.02692(15) Uani 1 1 d . . . C1 C 0.5707(3) 0.9042(4) 0.6907(3) 0.0390(8) Uani 1 1 d . . . H1A H 0.5801 0.9231 0.6143 0.047 Uiso 1 1 calc R . . H1B H 0.5381 0.9959 0.7094 0.047 Uiso 1 1 calc R . . C2 C 0.4623(3) 0.7949(4) 0.7363(3) 0.0401(8) Uani 1 1 d . . . H2A H 0.4502 0.7792 0.8125 0.048 Uiso 1 1 calc R . . H2B H 0.3702 0.8333 0.7088 0.048 Uiso 1 1 calc R . . C3 C 0.4259(3) 0.5358(4) 0.7709(3) 0.0425(9) Uani 1 1 d . . . H3A H 0.4391 0.5219 0.8450 0.051 Uiso 1 1 calc R . . H3B H 0.4636 0.4458 0.7515 0.051 Uiso 1 1 calc R . . C4 C 0.2669(3) 0.5610(3) 0.7573(3) 0.0329(7) Uani 1 1 d . . . C5 C 0.1669(4) 0.5730(4) 0.8403(3) 0.0432(9) Uani 1 1 d . . . H5A H 0.1969 0.5701 0.9059 0.052 Uiso 1 1 calc R . . C6 C 0.0220(3) 0.5894(4) 0.8259(3) 0.0426(9) Uani 1 1 d . . . H6A H -0.0433 0.5946 0.8837 0.051 Uiso 1 1 calc R . . C7 C 0.0689(4) 0.5883(5) 0.6533(3) 0.0438(9) Uani 1 1 d . . . H7A H 0.0367 0.5945 0.5879 0.053 Uiso 1 1 calc R . . C8 C 0.2145(4) 0.5694(5) 0.6624(3) 0.0478(9) Uani 1 1 d . . . H8A H 0.2779 0.5623 0.6040 0.057 Uiso 1 1 calc R . . C9 C 0.8286(3) 0.9356(4) 0.6799(3) 0.0373(7) Uani 1 1 d . . . H9A H 0.8393 0.9359 0.6057 0.045 Uiso 1 1 calc R . . H9B H 0.9176 0.8896 0.7098 0.045 Uiso 1 1 calc R . . C10 C 0.8075(3) 1.0937(3) 0.6888(3) 0.0323(7) Uani 1 1 d . . . C11 C 0.7274(4) 1.2041(4) 0.6192(3) 0.0362(7) Uani 1 1 d . . . H11A H 0.6864 1.1823 0.5647 0.043 Uiso 1 1 calc R . . C12 C 0.7098(3) 1.3452(3) 0.6318(2) 0.0334(7) Uani 1 1 d . . . H12A H 0.6558 1.4166 0.5850 0.040 Uiso 1 1 calc R . . C13 C 0.8437(3) 1.2790(4) 0.7744(3) 0.0342(7) Uani 1 1 d . . . H13A H 0.8846 1.3038 0.8278 0.041 Uiso 1 1 calc R . . C14 C 0.8654(3) 1.1348(3) 0.7673(3) 0.0347(7) Uani 1 1 d . . . H14A H 0.9190 1.0655 0.8156 0.042 Uiso 1 1 calc R . . C15 C 0.7049(4) 0.7254(4) 0.4784(3) 0.0375(7) Uani 1 1 d . . . C16 C 0.7736(5) 0.8056(6) 0.3728(3) 0.0706(14) Uani 1 1 d . . . H16A H 0.7054 0.8256 0.3206 0.106 Uiso 1 1 calc R . . H16B H 0.8559 0.7459 0.3520 0.106 Uiso 1 1 calc R . . H16C H 0.8029 0.8962 0.3789 0.106 Uiso 1 1 calc R . . C17 C 0.5286(4) 0.7705(4) 1.0308(3) 0.0407(8) Uani 1 1 d . . . C18 C 0.5193(5) 0.8589(5) 1.1118(3) 0.0582(11) Uani 1 1 d . . . H18A H 0.4221 0.8680 1.1422 0.087 Uiso 1 1 calc R . . H18B H 0.5487 0.9545 1.0784 0.087 Uiso 1 1 calc R . . H18C H 0.5813 0.8104 1.1662 0.087 Uiso 1 1 calc R . . N1 N 0.7117(3) 0.8457(3) 0.7325(2) 0.0295(6) Uani 1 1 d . . . H1C H 0.7040 0.8432 0.8025 0.035 Uiso 1 1 calc R . . N2 N 0.5110(2) 0.6540(3) 0.7089(2) 0.0284(5) Uani 1 1 d . . . H2C H 0.4943 0.6670 0.6401 0.034 Uiso 1 1 calc R . . N3 N -0.0294(3) 0.5981(3) 0.7340(2) 0.0275(5) Uani 1 1 d . . . N4 N 0.7667(3) 1.3846(3) 0.7082(2) 0.0275(5) Uani 1 1 d . . . O1 O 0.7840(2) 0.6924(3) 0.55458(18) 0.0377(5) Uani 1 1 d . . . O2 O 0.5790(3) 0.6970(4) 0.4840(2) 0.0679(9) Uani 1 1 d . . . O3 O 0.7084(2) 0.5305(2) 0.88869(17) 0.0326(5) Uani 1 1 d . . . O4 O 0.4181(3) 0.7204(3) 1.0150(2) 0.0533(7) Uani 1 1 d . . . O5 O 0.6501(3) 0.7486(3) 0.9833(2) 0.0540(7) Uani 1 1 d . . . O6 O 1.0976(4) 1.1763(4) 0.9608(4) 0.0965(13) Uani 1 1 d . . . O7 O 0.1649(4) 0.8932(4) 0.9274(3) 0.0844(11) 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 0.0192(2) 0.0245(2) 0.0375(2) -0.00741(15) -0.00496(15) -0.00216(14) C1 0.0308(17) 0.0258(16) 0.062(2) -0.0132(15) -0.0085(15) 0.0008(13) C2 0.0237(16) 0.0348(18) 0.063(2) -0.0161(16) -0.0034(15) 0.0031(13) C3 0.0213(15) 0.0363(18) 0.062(2) 0.0061(16) -0.0104(15) -0.0054(13) C4 0.0229(15) 0.0245(15) 0.0488(18) -0.0014(13) -0.0083(13) -0.0043(12) C5 0.0309(17) 0.065(2) 0.0351(17) -0.0108(16) -0.0087(14) -0.0092(16) C6 0.0211(15) 0.068(3) 0.0414(18) -0.0179(17) -0.0027(13) -0.0065(15) C7 0.0270(17) 0.066(3) 0.0401(19) -0.0164(17) -0.0051(14) -0.0017(16) C8 0.0248(16) 0.076(3) 0.0426(19) -0.0178(19) 0.0012(14) -0.0023(17) C9 0.0292(16) 0.0288(16) 0.053(2) -0.0106(15) 0.0021(14) -0.0048(13) C10 0.0268(15) 0.0255(15) 0.0439(18) -0.0073(13) 0.0021(13) -0.0074(12) C11 0.0446(19) 0.0292(16) 0.0378(17) -0.0102(13) -0.0084(14) -0.0070(14) C12 0.0370(17) 0.0284(16) 0.0347(16) -0.0056(13) -0.0076(13) -0.0028(13) C13 0.0346(17) 0.0319(17) 0.0386(17) -0.0105(13) -0.0112(13) -0.0015(13) C14 0.0318(16) 0.0262(16) 0.0445(18) -0.0037(13) -0.0126(14) 0.0006(13) C15 0.0362(18) 0.0397(19) 0.0363(17) -0.0108(14) -0.0072(14) 0.0042(14) C16 0.068(3) 0.088(4) 0.042(2) 0.007(2) -0.006(2) -0.005(3) C17 0.050(2) 0.0291(17) 0.0398(18) -0.0037(14) 0.0006(16) -0.0057(15) C18 0.074(3) 0.049(2) 0.053(2) -0.0187(19) 0.011(2) -0.013(2) N1 0.0241(13) 0.0266(13) 0.0392(14) -0.0102(11) -0.0029(11) -0.0028(10) N2 0.0157(11) 0.0259(13) 0.0417(14) -0.0040(11) -0.0043(10) -0.0022(9) N3 0.0192(12) 0.0286(13) 0.0348(13) -0.0061(10) -0.0060(10) -0.0030(10) N4 0.0235(12) 0.0250(13) 0.0357(13) -0.0092(10) -0.0048(10) -0.0033(10) O1 0.0306(12) 0.0436(14) 0.0371(12) -0.0046(10) -0.0070(10) -0.0050(10) O2 0.0391(15) 0.114(3) 0.0484(16) -0.0093(16) -0.0142(13) -0.0125(16) O3 0.0294(11) 0.0345(12) 0.0345(12) -0.0093(9) -0.0023(9) -0.0041(9) O4 0.0491(16) 0.0482(16) 0.0604(17) -0.0038(13) -0.0070(13) -0.0154(13) O5 0.0466(16) 0.0609(18) 0.0645(18) -0.0354(15) 0.0010(13) -0.0064(13) O6 0.054(2) 0.084(3) 0.159(4) -0.038(3) -0.020(2) -0.0116(19) O7 0.075(2) 0.079(3) 0.104(3) -0.032(2) -0.010(2) -0.0032(19) _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 O1 2.072(2) . ? Zn1 N3 2.160(2) 1_655 ? Zn1 N4 2.180(3) 1_545 ? Zn1 N2 2.183(2) . ? Zn1 O3 2.202(2) . ? Zn1 N1 2.258(3) . ? C1 N1 1.482(4) . ? C1 C2 1.509(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.481(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N2 1.473(4) . ? C3 C4 1.509(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C8 1.374(5) . ? C4 C5 1.378(5) . ? C5 C6 1.383(4) . ? C5 H5A 0.9300 . ? C6 N3 1.331(4) . ? C6 H6A 0.9300 . ? C7 N3 1.342(4) . ? C7 C8 1.375(5) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 N1 1.475(4) . ? C9 C10 1.523(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C14 1.381(5) . ? C10 C11 1.403(5) . ? C11 C12 1.381(5) . ? C11 H11A 0.9300 . ? C12 N4 1.343(4) . ? C12 H12A 0.9300 . ? C13 N4 1.342(4) . ? C13 C14 1.385(5) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 O2 1.237(4) . ? C15 O1 1.267(4) . ? C15 C16 1.516(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O4 1.254(4) . ? C17 O5 1.261(4) . ? C17 C18 1.508(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 H1C 0.9100 . ? N2 H2C 0.9100 . ? N3 Zn1 2.160(2) 1_455 ? N4 Zn1 2.180(3) 1_565 ? 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 Zn1 N3 89.67(10) . 1_655 ? O1 Zn1 N4 93.74(10) . 1_545 ? N3 Zn1 N4 89.76(10) 1_655 1_545 ? O1 Zn1 N2 92.99(10) . . ? N3 Zn1 N2 171.71(9) 1_655 . ? N4 Zn1 N2 97.89(9) 1_545 . ? O1 Zn1 O3 177.86(8) . . ? N3 Zn1 O3 88.30(9) 1_655 . ? N4 Zn1 O3 86.95(9) 1_545 . ? N2 Zn1 O3 88.92(9) . . ? O1 Zn1 N1 89.03(10) . . ? N3 Zn1 N1 91.63(10) 1_655 . ? N4 Zn1 N1 176.91(9) 1_545 . ? N2 Zn1 N1 80.58(9) . . ? O3 Zn1 N1 90.33(9) . . ? N1 C1 C2 109.7(3) . . ? N1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? N1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? N2 C2 C1 110.3(3) . . ? N2 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? N2 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N2 C3 C4 115.3(3) . . ? N2 C3 H3A 108.4 . . ? C4 C3 H3A 108.4 . . ? N2 C3 H3B 108.4 . . ? C4 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? C8 C4 C5 116.7(3) . . ? C8 C4 C3 121.7(3) . . ? C5 C4 C3 121.6(3) . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? N3 C6 C5 123.7(3) . . ? N3 C6 H6A 118.2 . . ? C5 C6 H6A 118.2 . . ? N3 C7 C8 123.4(3) . . ? N3 C7 H7A 118.3 . . ? C8 C7 H7A 118.3 . . ? C4 C8 C7 120.3(3) . . ? C4 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? N1 C9 C10 115.1(3) . . ? N1 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? N1 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C14 C10 C11 116.6(3) . . ? C14 C10 C9 121.2(3) . . ? C11 C10 C9 122.2(3) . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? N4 C12 C11 123.3(3) . . ? N4 C12 H12A 118.4 . . ? C11 C12 H12A 118.4 . . ? N4 C13 C14 123.3(3) . . ? N4 C13 H13A 118.4 . . ? C14 C13 H13A 118.4 . . ? C10 C14 C13 120.2(3) . . ? C10 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? O2 C15 O1 125.3(3) . . ? O2 C15 C16 118.8(3) . . ? O1 C15 C16 115.9(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 O5 123.2(4) . . ? O4 C17 C18 119.5(3) . . ? O5 C17 C18 117.2(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C9 N1 C1 113.1(3) . . ? C9 N1 Zn1 114.50(19) . . ? C1 N1 Zn1 104.33(18) . . ? C9 N1 H1C 108.2 . . ? C1 N1 H1C 108.2 . . ? Zn1 N1 H1C 108.2 . . ? C3 N2 C2 111.7(3) . . ? C3 N2 Zn1 116.20(19) . . ? C2 N2 Zn1 108.54(18) . . ? C3 N2 H2C 106.6 . . ? C2 N2 H2C 106.6 . . ? Zn1 N2 H2C 106.6 . . ? C6 N3 C7 116.0(3) . . ? C6 N3 Zn1 122.7(2) . 1_455 ? C7 N3 Zn1 121.2(2) . 1_455 ? C13 N4 C12 116.8(3) . . ? C13 N4 Zn1 122.5(2) . 1_565 ? C12 N4 Zn1 120.6(2) . 1_565 ? C15 O1 Zn1 133.2(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.655 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.078 data_a2 _database_code_depnum_ccdc_archive 'CCDC 912060' #TrackingRef 'ClO4-5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H30 Cl2 N4 O14 Zn' _chemical_formula_weight 614.69 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)/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 9.413(5) _cell_length_b 18.542(9) _cell_length_c 15.016(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.205(8) _cell_angle_gamma 90.00 _cell_volume 2579(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7376 _cell_measurement_theta_min 2.1967 _cell_measurement_theta_max 27.4745 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 1.230 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.68382 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Mercury2 (1x1 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number 6037 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20109 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5844 _reflns_number_gt 4572 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.1849P)^2^+1.2571P] 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 5844 _refine_ls_number_parameters 390 _refine_ls_number_restraints 406 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0778 _refine_ls_wR_factor_ref 0.2639 _refine_ls_wR_factor_gt 0.2472 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.135 _refine_ls_shift/su_max 0.067 _refine_ls_shift/su_mean 0.005 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 0.95500(5) 0.88187(2) 0.23556(3) 0.0360(2) Uani 1 1 d . . . C1 C 0.8076(6) 0.7449(3) 0.2643(6) 0.0787(19) Uani 1 1 d U . . H1A H 0.7818 0.6965 0.2426 0.094 Uiso 1 1 calc R . . H1B H 0.8215 0.7439 0.3298 0.094 Uiso 1 1 calc R . . C2 C 0.6925(6) 0.7915(3) 0.2318(6) 0.081(2) Uani 1 1 d U . . H2A H 0.6107 0.7787 0.2599 0.097 Uiso 1 1 calc R . . H2B H 0.6642 0.7843 0.1671 0.097 Uiso 1 1 calc R . . C3 C 0.6217(5) 0.9139(3) 0.1899(4) 0.0576(14) Uani 1 1 d . . . H3A H 0.6286 0.9027 0.1277 0.069 Uiso 1 1 calc R . . H3B H 0.6464 0.9644 0.2000 0.069 Uiso 1 1 calc R . . C4 C 0.4671(5) 0.9029(3) 0.2024(4) 0.0491(11) Uani 1 1 d . . . C5 C 0.4156(6) 0.9379(3) 0.2712(5) 0.0631(15) Uani 1 1 d . . . H5A H 0.4754 0.9678 0.3112 0.076 Uiso 1 1 calc R . . C6 C 0.2718(5) 0.9275(3) 0.2793(4) 0.0576(14) Uani 1 1 d . . . H6A H 0.2372 0.9517 0.3254 0.069 Uiso 1 1 calc R . . C7 C 0.2316(5) 0.8516(3) 0.1592(4) 0.0479(10) Uani 1 1 d . . . H7A H 0.1698 0.8222 0.1197 0.057 Uiso 1 1 calc R . . C8 C 0.3741(5) 0.8588(3) 0.1468(4) 0.0551(12) Uani 1 1 d . . . H8A H 0.4062 0.8335 0.1006 0.066 Uiso 1 1 calc R . . C9 C 1.0661(6) 0.7284(2) 0.2985(4) 0.0534(12) Uani 1 1 d . . . H9A H 1.0616 0.7411 0.3606 0.064 Uiso 1 1 calc R . . H9B H 1.1574 0.7457 0.2854 0.064 Uiso 1 1 calc R . . C10 C 1.0605(5) 0.6467(2) 0.2889(4) 0.0472(10) Uani 1 1 d . . . C11 C 1.0030(7) 0.6038(3) 0.3495(4) 0.0553(13) Uani 1 1 d . . . H11A H 0.9675 0.6247 0.3974 0.066 Uiso 1 1 calc R . . C12 C 0.9991(6) 0.5301(2) 0.3379(4) 0.0509(12) Uani 1 1 d . . . H12A H 0.9573 0.5022 0.3779 0.061 Uiso 1 1 calc R . . C13 C 1.1054(5) 0.5379(2) 0.2135(3) 0.0455(10) Uani 1 1 d . . . H13A H 1.1394 0.5157 0.1658 0.055 Uiso 1 1 calc R . . C14 C 1.1123(6) 0.6127(2) 0.2206(4) 0.0493(12) Uani 1 1 d . . . H14A H 1.1521 0.6396 0.1788 0.059 Uiso 1 1 calc R . . N1 N 0.9453(4) 0.7651(2) 0.2368(3) 0.0402(9) Uani 1 1 d . . . H1C H 0.9442 0.7489 0.1795 0.048 Uiso 1 1 calc R . . N2 N 0.7271(4) 0.8704(2) 0.2496(3) 0.0423(9) Uani 1 1 d . . . H2C H 0.7195 0.8804 0.3079 0.051 Uiso 1 1 calc R . . N3 N 1.0516(3) 0.4968(2) 0.2729(2) 0.0383(8) Uani 1 1 d . . . N4 N 0.1808(4) 0.88476(18) 0.2248(3) 0.0412(9) Uani 1 1 d . . . O1 O 0.8949(4) 0.87812(18) 0.0865(3) 0.0521(9) Uani 1 1 d . . . O2 O 1.0211(5) 0.88583(19) 0.3847(3) 0.0534(9) Uani 1 1 d . . . O3 O 0.7433(6) 0.9888(3) -0.0115(4) 0.0886(15) Uani 1 1 d . . . O4 O 0.9583(9) 0.7437(3) 0.0307(4) 0.122(2) Uani 1 1 d . . . O5 O 1.2383(7) 0.8085(4) 0.4927(4) 0.108(2) Uani 1 1 d . . . O6 O 1.4137(12) 0.6168(5) 0.1243(7) 0.167(4) Uani 1 1 d U . . Cl1 Cl 1.4853(2) 0.65039(12) 0.39234(13) 0.0870(8) Uani 0.503(7) 1 d PD A 1 O11 O 1.3787(13) 0.6898(7) 0.4319(9) 0.140(5) Uani 0.503(7) 1 d PDU A 1 O12 O 1.4600(16) 0.6692(8) 0.2967(5) 0.132(5) Uani 0.503(7) 1 d PDU A 1 O13 O 1.4602(14) 0.5749(4) 0.4003(10) 0.115(4) Uani 0.503(7) 1 d PDU A 1 O14 O 1.6277(10) 0.6684(8) 0.4334(10) 0.126(6) Uani 0.503(7) 1 d PDU A 1 Cl1A Cl 1.4853(2) 0.65039(12) 0.39234(13) 0.0870(8) Uani 0.50 1 d PD A 2 O15 O 1.5809(19) 0.6825(11) 0.4673(10) 0.148(6) Uani 0.497(7) 1 d PDU A 2 O16 O 1.568(2) 0.6080(10) 0.3406(13) 0.186(7) Uani 0.497(7) 1 d PDU A 2 O17 O 1.4141(18) 0.7051(8) 0.3331(12) 0.153(6) Uani 0.497(7) 1 d PDU A 2 O18 O 1.386(2) 0.6099(11) 0.4321(13) 0.174(7) Uani 0.497(7) 1 d PDU A 2 Cl2 Cl 0.7370(3) 0.57552(15) 0.01603(15) 0.1021(9) Uani 0.260(7) 1 d PD B 1 O21 O 0.7542(13) 0.6479(4) 0.0360(7) 0.043(3) Uani 0.260(7) 1 d PDU B 1 O22 O 0.652(2) 0.5393(9) 0.0730(12) 0.124(6) Uani 0.260(7) 1 d PDU B 1 O23 O 0.677(2) 0.5620(11) -0.0773(7) 0.140(7) Uani 0.260(7) 1 d PDU B 1 O24 O 0.8805(15) 0.5406(11) 0.0328(17) 0.148(8) Uani 0.260(7) 1 d PDU B 1 Cl2A Cl 0.7370(3) 0.57552(15) 0.01603(15) 0.1021(9) Uani 0.74 1 d PD B 2 O25 O 0.7011(15) 0.6364(6) -0.0393(9) 0.178(5) Uani 0.740(7) 1 d PDU B 2 O26 O 0.7533(15) 0.6009(8) 0.1089(6) 0.165(5) Uani 0.740(7) 1 d PDU B 2 O27 O 0.6120(14) 0.5278(8) 0.0060(11) 0.216(6) Uani 0.740(7) 1 d PDU B 2 O28 O 0.8630(13) 0.5413(8) -0.0014(9) 0.183(5) Uani 0.740(7) 1 d PDU 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 Zn1 0.0242(3) 0.0253(3) 0.0617(4) 0.00001(17) 0.0162(2) 0.00019(15) C1 0.050(3) 0.037(2) 0.158(6) 0.002(3) 0.041(4) -0.007(2) C2 0.045(3) 0.043(3) 0.162(6) 0.009(3) 0.038(4) -0.003(2) C3 0.027(2) 0.065(3) 0.085(4) 0.024(3) 0.019(2) 0.002(2) C4 0.023(2) 0.051(3) 0.075(3) 0.013(2) 0.015(2) 0.0034(18) C5 0.035(3) 0.055(3) 0.101(4) -0.020(3) 0.016(3) -0.007(2) C6 0.031(2) 0.059(3) 0.087(4) -0.026(3) 0.022(2) -0.006(2) C7 0.028(2) 0.049(3) 0.068(3) -0.009(2) 0.0125(19) -0.0008(18) C8 0.035(2) 0.071(3) 0.064(3) -0.004(2) 0.020(2) 0.008(2) C9 0.065(3) 0.025(2) 0.067(3) 0.0028(19) 0.003(2) -0.001(2) C10 0.049(3) 0.028(2) 0.064(3) 0.0021(19) 0.007(2) 0.0012(18) C11 0.076(4) 0.032(2) 0.065(3) -0.0001(19) 0.031(3) 0.009(2) C12 0.062(3) 0.028(2) 0.070(3) 0.0050(19) 0.033(2) 0.0040(19) C13 0.041(2) 0.034(2) 0.067(3) 0.0023(19) 0.025(2) 0.0005(18) C14 0.050(3) 0.031(2) 0.072(3) 0.0098(19) 0.025(2) 0.0002(18) N1 0.0298(18) 0.0250(17) 0.068(2) -0.0030(13) 0.0159(17) 0.0015(12) N2 0.0219(17) 0.0382(18) 0.072(2) 0.0063(16) 0.0212(16) 0.0019(14) N3 0.0329(19) 0.0232(16) 0.063(2) 0.0010(13) 0.0200(17) 0.0007(12) N4 0.0192(16) 0.0365(19) 0.071(3) -0.0029(15) 0.0180(16) -0.0003(12) O1 0.046(2) 0.052(2) 0.060(2) 0.0024(14) 0.0135(16) 0.0062(15) O2 0.053(2) 0.054(2) 0.055(2) -0.0071(14) 0.0138(17) 0.0014(15) O3 0.085(3) 0.083(3) 0.096(3) 0.028(3) 0.011(3) 0.017(3) O4 0.179(7) 0.087(4) 0.101(4) -0.034(3) 0.029(4) 0.029(4) O5 0.097(4) 0.107(4) 0.107(4) 0.008(3) -0.017(3) 0.011(3) O6 0.144(7) 0.220(8) 0.139(6) 0.035(5) 0.031(5) 0.061(6) Cl1 0.0816(13) 0.0955(15) 0.0815(12) 0.0132(9) 0.0078(9) -0.0145(10) O11 0.139(10) 0.137(10) 0.148(10) -0.007(8) 0.037(8) 0.068(8) O12 0.153(11) 0.141(11) 0.111(9) 0.014(8) 0.048(8) -0.034(9) O13 0.101(9) 0.066(6) 0.182(11) 0.017(7) 0.033(8) -0.013(6) O14 0.086(8) 0.117(10) 0.159(11) 0.042(9) -0.022(9) -0.016(8) Cl1A 0.0816(13) 0.0955(15) 0.0815(12) 0.0132(9) 0.0078(9) -0.0145(10) O15 0.146(12) 0.149(12) 0.147(12) -0.001(10) 0.018(10) -0.044(11) O16 0.169(13) 0.173(13) 0.217(14) 0.003(12) 0.038(13) 0.023(11) O17 0.134(9) 0.141(9) 0.179(9) 0.034(7) 0.009(7) -0.009(7) O18 0.171(13) 0.184(13) 0.170(13) 0.030(11) 0.036(11) -0.081(11) Cl2 0.0865(15) 0.137(2) 0.0879(14) 0.0157(12) 0.0292(11) -0.0105(13) O21 0.055(6) 0.059(6) 0.022(4) -0.004(4) 0.028(4) -0.007(5) O22 0.125(13) 0.185(15) 0.083(11) 0.040(11) 0.076(10) 0.042(12) O23 0.145(14) 0.207(16) 0.076(11) 0.027(12) 0.045(11) -0.008(14) O24 0.129(14) 0.229(16) 0.099(14) 0.024(13) 0.059(11) 0.052(14) Cl2A 0.0865(15) 0.137(2) 0.0879(14) 0.0157(12) 0.0292(11) -0.0105(13) O25 0.178(10) 0.178(10) 0.180(10) 0.081(8) 0.041(9) 0.003(9) O26 0.174(10) 0.225(11) 0.099(7) -0.010(7) 0.033(7) 0.025(9) O27 0.185(11) 0.231(12) 0.230(12) 0.031(11) 0.035(10) -0.056(10) O28 0.178(10) 0.257(12) 0.143(9) 0.050(8) 0.108(7) 0.039(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 Zn1 N3 2.135(4) 2_755 ? Zn1 N4 2.161(4) 1_655 ? Zn1 N1 2.167(4) . ? Zn1 N2 2.203(4) . ? Zn1 O1 2.210(4) . ? Zn1 O2 2.217(4) . ? C1 C2 1.404(9) . ? C1 N1 1.477(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.513(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N2 1.457(6) . ? C3 C4 1.513(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C8 1.369(8) . ? C4 C5 1.379(8) . ? C5 C6 1.394(7) . ? C5 H5A 0.9300 . ? C6 N4 1.335(6) . ? C6 H6A 0.9300 . ? C7 N4 1.321(6) . ? C7 C8 1.393(6) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 N1 1.497(6) . ? C9 C10 1.523(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C14 1.364(7) . ? C10 C11 1.388(7) . ? C11 C12 1.378(6) . ? C11 H11A 0.9300 . ? C12 N3 1.323(6) . ? C12 H12A 0.9300 . ? C13 N3 1.339(5) . ? C13 C14 1.392(6) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? N1 H1C 0.9100 . ? N2 H2C 0.9100 . ? N3 Zn1 2.135(4) 2_745 ? N4 Zn1 2.161(4) 1_455 ? Cl1 O14 1.412(7) . ? Cl1 O13 1.428(7) . ? Cl1 O11 1.451(7) . ? Cl1 O12 1.456(7) . ? Cl2 O21 1.378(8) . ? Cl2 O22 1.437(8) . ? Cl2 O23 1.437(8) . ? Cl2 O24 1.480(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Zn1 N4 89.38(12) 2_755 1_655 ? N3 Zn1 N1 175.45(14) 2_755 . ? N4 Zn1 N1 93.94(12) 1_655 . ? N3 Zn1 N2 94.80(13) 2_755 . ? N4 Zn1 N2 175.70(14) 1_655 . ? N1 Zn1 N2 81.93(13) . . ? N3 Zn1 O1 88.39(13) 2_755 . ? N4 Zn1 O1 90.21(16) 1_655 . ? N1 Zn1 O1 88.49(14) . . ? N2 Zn1 O1 90.88(16) . . ? N3 Zn1 O2 91.54(13) 2_755 . ? N4 Zn1 O2 88.34(16) 1_655 . ? N1 Zn1 O2 91.67(14) . . ? N2 Zn1 O2 90.56(16) . . ? O1 Zn1 O2 178.55(13) . . ? C2 C1 N1 114.1(5) . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? N1 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C1 C2 N2 113.9(5) . . ? C1 C2 H2A 108.8 . . ? N2 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? N2 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? N2 C3 C4 114.5(4) . . ? N2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? N2 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C8 C4 C5 117.8(4) . . ? C8 C4 C3 122.0(5) . . ? C5 C4 C3 120.2(5) . . ? C4 C5 C6 118.5(5) . . ? C4 C5 H5A 120.8 . . ? C6 C5 H5A 120.8 . . ? N4 C6 C5 123.7(5) . . ? N4 C6 H6A 118.1 . . ? C5 C6 H6A 118.1 . . ? N4 C7 C8 122.7(5) . . ? N4 C7 H7A 118.7 . . ? C8 C7 H7A 118.7 . . ? C4 C8 C7 120.2(5) . . ? C4 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? N1 C9 C10 112.6(4) . . ? N1 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N1 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C14 C10 C11 117.4(4) . . ? C14 C10 C9 121.3(4) . . ? C11 C10 C9 121.2(5) . . ? C12 C11 C10 119.4(5) . . ? C12 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? N3 C12 C11 123.4(4) . . ? N3 C12 H12A 118.3 . . ? C11 C12 H12A 118.3 . . ? N3 C13 C14 122.3(4) . . ? N3 C13 H13A 118.9 . . ? C14 C13 H13A 118.9 . . ? C10 C14 C13 120.0(4) . . ? C10 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C1 N1 C9 108.6(4) . . ? C1 N1 Zn1 107.2(3) . . ? C9 N1 Zn1 115.5(3) . . ? C1 N1 H1C 108.4 . . ? C9 N1 H1C 108.4 . . ? Zn1 N1 H1C 108.4 . . ? C3 N2 C2 108.9(5) . . ? C3 N2 Zn1 117.1(3) . . ? C2 N2 Zn1 105.0(3) . . ? C3 N2 H2C 108.5 . . ? C2 N2 H2C 108.5 . . ? Zn1 N2 H2C 108.5 . . ? C12 N3 C13 117.5(4) . . ? C12 N3 Zn1 119.9(3) . 2_745 ? C13 N3 Zn1 122.6(3) . 2_745 ? C7 N4 C6 117.1(4) . . ? C7 N4 Zn1 122.4(3) . 1_455 ? C6 N4 Zn1 120.1(3) . 1_455 ? O14 Cl1 O13 110.7(6) . . ? O14 Cl1 O11 111.9(7) . . ? O13 Cl1 O11 108.9(7) . . ? O14 Cl1 O12 110.5(7) . . ? O13 Cl1 O12 108.5(6) . . ? O11 Cl1 O12 106.2(6) . . ? O21 Cl2 O22 112.4(7) . . ? O21 Cl2 O23 113.1(8) . . ? O22 Cl2 O23 109.5(8) . . ? O21 Cl2 O24 108.7(8) . . ? O22 Cl2 O24 106.4(8) . . ? O23 Cl2 O24 106.2(7) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.383 _refine_diff_density_min -1.079 _refine_diff_density_rms 0.120 data_a3 _database_code_depnum_ccdc_archive 'CCDC 912061' #TrackingRef 'KSCN-3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 N6 O2 S2 Zn' _chemical_formula_weight 459.89 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' S S 0.1246 0.1234 '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 orthorhombic _symmetry_space_group_name_H-M fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 17.083(12) _cell_length_b 22.908(16) _cell_length_c 23.481(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9189(11) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6811 _cell_measurement_theta_min 2.3846 _cell_measurement_theta_max 27.4739 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3808 _exptl_absorpt_coefficient_mu 1.272 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4242 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Saturn724+ (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8114 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.39 _reflns_number_total 2557 _reflns_number_gt 1908 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.1637P)^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 2557 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.2599 _refine_ls_wR_factor_gt 0.2358 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.082 _refine_ls_shift/su_mean 0.002 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 0.6250 -0.05282(3) 0.6250 0.0946(13) Uani 1 2 d S . . N3 N 0.5136(3) -0.0532(2) 0.6646(2) 0.1127(18) Uani 1 1 d . . . C8 C 0.4541(4) -0.0410(3) 0.6802(2) 0.120(2) Uani 1 1 d . . . C2 C 0.5118(4) -0.1399(2) 0.5529(3) 0.116(2) Uani 1 1 d . . . H2A H 0.4819 -0.1400 0.5880 0.139 Uiso 1 1 calc R . . H2B H 0.5083 -0.1787 0.5363 0.139 Uiso 1 1 calc R . . C3 C 0.4760(3) -0.09662(19) 0.51235(19) 0.0986(17) Uani 1 1 d . . . C7 C 0.4230(3) -0.0547(2) 0.52953(19) 0.0963(17) Uani 1 1 d . . . H7A H 0.4074 -0.0525 0.5674 0.116 Uiso 1 1 calc R . . C4 C 0.4959(3) -0.0979(2) 0.4548(2) 0.1043(18) Uani 1 1 d . . . H4A H 0.5304 -0.1262 0.4412 0.125 Uiso 1 1 calc R . . C6 C 0.3932(2) -0.0159(2) 0.48956(19) 0.0921(17) Uani 1 1 d . . . H6A H 0.3574 0.0120 0.5018 0.111 Uiso 1 1 calc R . . C5 C 0.4645(3) -0.0574(2) 0.4180(2) 0.1016(17) Uani 1 1 d . . . H5A H 0.4796 -0.0585 0.3799 0.122 Uiso 1 1 calc R . . C1 C 0.6338(4) -0.1778(3) 0.5936(3) 0.135(3) Uani 1 1 d . . . H1A H 0.6899 -0.1753 0.5877 0.162 Uiso 1 1 calc R . . H1B H 0.6154 -0.2138 0.5766 0.162 Uiso 1 1 calc R . . N1 N 0.5944(3) -0.12716(16) 0.5661(2) 0.1070(18) Uani 1 1 d . . . H1C H 0.6193 -0.1205 0.5325 0.128 Uiso 1 1 calc R . . N2 N 0.4131(2) -0.01645(15) 0.43469(14) 0.0905(16) Uani 1 1 d . . . S1 S 0.36569(17) -0.0226(2) 0.70152(16) 0.231(2) Uani 1 1 d . . . O1 O 0.7197(14) -0.1143(9) 0.4287(10) 0.55(2) 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 0.0967(14) 0.0952(14) 0.0919(14) 0.000 -0.0159(3) 0.000 N3 0.100(3) 0.135(4) 0.103(3) 0.006(2) -0.004(2) -0.013(2) C8 0.116(4) 0.147(5) 0.097(4) -0.006(3) -0.003(3) -0.007(3) C2 0.129(4) 0.100(3) 0.119(4) 0.004(2) -0.044(3) -0.010(3) C3 0.107(3) 0.094(3) 0.095(3) 0.0005(19) -0.025(2) -0.014(2) C7 0.096(3) 0.108(3) 0.085(3) 0.0071(19) -0.014(2) -0.016(2) C4 0.114(3) 0.090(3) 0.110(3) -0.013(2) -0.029(2) 0.005(2) C6 0.091(3) 0.095(3) 0.089(3) -0.0031(18) -0.0110(19) -0.0056(18) C5 0.116(3) 0.097(3) 0.092(3) -0.0134(19) -0.015(2) 0.007(2) C1 0.164(5) 0.102(4) 0.138(5) -0.025(3) -0.070(4) 0.020(3) N1 0.119(3) 0.097(3) 0.105(3) -0.0074(17) -0.033(2) 0.0030(18) N2 0.100(2) 0.091(2) 0.081(2) -0.0047(14) -0.0137(16) -0.0053(16) S1 0.155(2) 0.337(5) 0.200(3) -0.044(3) 0.0432(17) 0.044(2) O1 0.54(3) 0.353(19) 0.77(5) 0.10(3) -0.38(3) -0.16(2) _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 2.118(5) . ? Zn1 N3 2.118(5) 11 ? Zn1 N2 2.215(4) 19_656 ? Zn1 N2 2.215(4) 17_656 ? Zn1 N1 2.255(4) 11 ? Zn1 N1 2.255(4) . ? N3 C8 1.115(8) . ? C8 S1 1.646(8) . ? C2 N1 1.475(7) . ? C2 C3 1.504(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C7 1.381(7) . ? C3 C4 1.395(7) . ? C7 C6 1.389(6) . ? C7 H7A 0.9300 . ? C4 C5 1.377(7) . ? C4 H4A 0.9300 . ? C6 N2 1.333(6) . ? C6 H6A 0.9300 . ? C5 N2 1.345(6) . ? C5 H5A 0.9300 . ? C1 N1 1.488(7) . ? C1 C1 1.505(15) 11 ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? N1 H1C 0.9100 . ? N2 Zn1 2.215(4) 17_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Zn1 N3 179.6(3) . 11 ? N3 Zn1 N2 89.35(17) . 19_656 ? N3 Zn1 N2 90.96(16) 11 19_656 ? N3 Zn1 N2 90.96(16) . 17_656 ? N3 Zn1 N2 89.35(17) 11 17_656 ? N2 Zn1 N2 88.47(17) 19_656 17_656 ? N3 Zn1 N1 86.32(19) . 11 ? N3 Zn1 N1 93.36(19) 11 11 ? N2 Zn1 N1 94.88(14) 19_656 11 ? N2 Zn1 N1 175.66(14) 17_656 11 ? N3 Zn1 N1 93.36(19) . . ? N3 Zn1 N1 86.32(19) 11 . ? N2 Zn1 N1 175.66(14) 19_656 . ? N2 Zn1 N1 94.88(14) 17_656 . ? N1 Zn1 N1 81.9(2) 11 . ? C8 N3 Zn1 164.0(5) . . ? N3 C8 S1 178.6(6) . . ? N1 C2 C3 113.0(4) . . ? N1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C7 C3 C4 117.3(4) . . ? C7 C3 C2 122.7(5) . . ? C4 C3 C2 120.0(5) . . ? C3 C7 C6 119.2(4) . . ? C3 C7 H7A 120.4 . . ? C6 C7 H7A 120.4 . . ? C5 C4 C3 119.9(5) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? N2 C6 C7 123.6(4) . . ? N2 C6 H6A 118.2 . . ? C7 C6 H6A 118.2 . . ? N2 C5 C4 122.8(5) . . ? N2 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? N1 C1 C1 109.5(5) . 11 ? N1 C1 H1A 109.8 . . ? C1 C1 H1A 109.8 11 . ? N1 C1 H1B 109.8 . . ? C1 C1 H1B 109.8 11 . ? H1A C1 H1B 108.2 . . ? C2 N1 C1 111.7(5) . . ? C2 N1 Zn1 120.0(4) . . ? C1 N1 Zn1 102.6(3) . . ? C2 N1 H1C 107.3 . . ? C1 N1 H1C 107.3 . . ? Zn1 N1 H1C 107.3 . . ? C6 N2 C5 117.1(4) . . ? C6 N2 Zn1 122.0(3) . 17_656 ? C5 N2 Zn1 120.5(3) . 17_656 ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.041 _refine_diff_density_min -0.018 _refine_diff_density_rms 0.004 data_a4 _database_code_depnum_ccdc_archive 'CCDC 912062' #TrackingRef 'NaCl-4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H21 Cl2 N4 O1.50 Zn' _chemical_formula_weight 405.62 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 orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 14.429(4) _cell_length_b 19.030(5) _cell_length_c 24.580(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6750(3) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5392 _cell_measurement_theta_min 2.7067 _cell_measurement_theta_max 27.4816 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3344 _exptl_absorpt_coefficient_mu 1.782 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7697 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Saturn724+ (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14208 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3705 _reflns_number_gt 3502 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0422P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.454(12) _refine_ls_number_reflns 3705 _refine_ls_number_parameters 206 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0766 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.5000 0.0000 0.480286(17) 0.02766(13) Uani 1 2 d S . . Zn2 Zn 0.0000 0.0000 0.584428(18) 0.02781(13) Uani 1 2 d S . . Cl1 Cl -0.03438(5) 0.13143(4) 0.59227(4) 0.03456(19) Uani 1 1 d . . . Cl2 Cl 0.54752(5) 0.12808(4) 0.47641(4) 0.03420(19) Uani 1 1 d . . . C7 C 0.4588(2) 0.02501(17) 0.36099(15) 0.0303(7) Uani 1 1 d . . . H7A H 0.4807 0.0732 0.3619 0.036 Uiso 1 1 calc R . . H7B H 0.4230 0.0186 0.3280 0.036 Uiso 1 1 calc R . . C2 C 0.23832(19) -0.02384(16) 0.47283(12) 0.0287(6) Uani 1 1 d . . . H2A H 0.2839 -0.0577 0.4674 0.034 Uiso 1 1 calc R . . C6 C 0.3184(2) 0.05737(18) 0.40669(15) 0.0332(8) Uani 1 1 d . . . H6A H 0.2952 0.0578 0.3697 0.040 Uiso 1 1 calc R . . H6B H 0.3380 0.1048 0.4154 0.040 Uiso 1 1 calc R . . C8 C 0.1735(2) 0.06853(18) 0.65346(15) 0.0338(8) Uani 1 1 d . . . H8A H 0.1976 0.0726 0.6902 0.041 Uiso 1 1 calc R . . H8B H 0.1462 0.1134 0.6438 0.041 Uiso 1 1 calc R . . C3 C 0.2403(2) 0.03777(17) 0.44394(15) 0.0273(7) Uani 1 1 d . . . C1 C 0.16800(19) -0.03557(15) 0.51026(13) 0.0288(6) Uani 1 1 d . . . H1A H 0.1680 -0.0774 0.5298 0.035 Uiso 1 1 calc R . . C5 C 0.0987(2) 0.06847(16) 0.48813(14) 0.0344(7) Uani 1 1 d . . . H5A H 0.0497 0.0998 0.4920 0.041 Uiso 1 1 calc R . . C4 C 0.1663(2) 0.08334(17) 0.45074(13) 0.0348(7) Uani 1 1 d . . . H4A H 0.1625 0.1240 0.4299 0.042 Uiso 1 1 calc R . . C14 C 0.0397(2) 0.02539(18) 0.70108(16) 0.0305(7) Uani 1 1 d . . . H14A H 0.0160 0.0731 0.7007 0.037 Uiso 1 1 calc R . . H14B H 0.0758 0.0193 0.7340 0.037 Uiso 1 1 calc R . . C9 C 0.25319(18) 0.05385(18) 0.61524(15) 0.0286(7) Uani 1 1 d . . . C10 C 0.3048(2) -0.00787(16) 0.61789(13) 0.0324(7) Uani 1 1 d . . . H10A H 0.2904 -0.0419 0.6437 0.039 Uiso 1 1 calc R . . C11 C 0.37724(19) -0.01860(16) 0.58208(13) 0.0316(6) Uani 1 1 d . . . H11A H 0.4110 -0.0601 0.5848 0.038 Uiso 1 1 calc R . . C13 C 0.2804(2) 0.10326(16) 0.57684(13) 0.0322(7) Uani 1 1 d . . . H13A H 0.2493 0.1460 0.5742 0.039 Uiso 1 1 calc R . . C12 C 0.35381(19) 0.08856(15) 0.54254(13) 0.0322(7) Uani 1 1 d . . . H12A H 0.3714 0.1225 0.5173 0.039 Uiso 1 1 calc R . . N2 N 0.39979(19) 0.01129(14) 0.40883(11) 0.0269(6) Uani 1 1 d . . . H2B H 0.3770 -0.0327 0.4034 0.032 Uiso 1 1 calc R . . N3 N 0.09975(19) 0.01416(14) 0.65299(11) 0.0245(6) Uani 1 1 d . . . H3A H 0.1284 -0.0280 0.6579 0.029 Uiso 1 1 calc R . . N1 N 0.10011(17) 0.01101(14) 0.51926(11) 0.0269(6) Uani 1 1 d . . . N4 N 0.40105(17) 0.02792(14) 0.54376(11) 0.0279(6) Uani 1 1 d . . . O1 O 0.0785(2) 0.24243(17) 0.5208(2) 0.0926(15) Uani 1 1 d . . . O2 O 0.2500 0.2500 0.4609(3) 0.109(2) Uani 1 2 d S . . 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 0.0266(2) 0.0301(3) 0.0263(3) 0.000 0.000 -0.00072(19) Zn2 0.0240(2) 0.0349(3) 0.0246(3) 0.000 0.000 0.0011(2) Cl1 0.0398(4) 0.0260(4) 0.0378(5) -0.0019(3) 0.0026(4) 0.0033(3) Cl2 0.0337(3) 0.0275(4) 0.0413(5) 0.0030(3) 0.0051(4) -0.0018(3) C7 0.0276(14) 0.0403(19) 0.0228(18) 0.0046(15) -0.0009(13) -0.0051(14) C2 0.0247(12) 0.0279(14) 0.0333(16) -0.0031(12) 0.0022(13) 0.0013(11) C6 0.0267(14) 0.0348(18) 0.038(2) 0.0057(15) -0.0006(14) -0.0012(13) C8 0.0278(14) 0.0347(18) 0.039(2) -0.0094(15) 0.0052(14) -0.0045(13) C3 0.0244(13) 0.0303(17) 0.0271(16) -0.0033(13) -0.0012(12) -0.0015(12) C1 0.0238(12) 0.0274(15) 0.0351(17) -0.0007(13) -0.0001(12) -0.0001(11) C5 0.0291(13) 0.0377(17) 0.0365(17) 0.0048(14) 0.0030(13) 0.0125(13) C4 0.0343(15) 0.0379(17) 0.0323(16) 0.0094(14) 0.0002(13) 0.0062(13) C14 0.0258(15) 0.043(2) 0.0222(16) -0.0031(15) -0.0008(13) 0.0009(14) C9 0.0228(13) 0.0332(17) 0.0298(19) -0.0086(14) -0.0028(12) -0.0024(11) C10 0.0359(16) 0.0352(17) 0.0262(15) 0.0083(13) 0.0023(13) 0.0001(13) C11 0.0288(13) 0.0304(15) 0.0354(17) 0.0087(13) 0.0058(13) 0.0054(12) C13 0.0315(13) 0.0244(15) 0.0407(18) -0.0005(13) -0.0006(13) 0.0006(12) C12 0.0325(14) 0.0264(15) 0.0376(18) 0.0022(13) 0.0014(13) -0.0031(12) N2 0.0247(12) 0.0281(14) 0.0280(16) -0.0036(12) 0.0043(12) -0.0015(11) N3 0.0206(12) 0.0267(13) 0.0262(15) -0.0044(11) -0.0018(11) 0.0031(11) N1 0.0204(11) 0.0350(14) 0.0252(15) 0.0011(11) -0.0012(11) 0.0008(10) N4 0.0231(11) 0.0315(14) 0.0290(16) 0.0016(11) -0.0012(11) 0.0013(11) O1 0.083(2) 0.0569(19) 0.138(4) 0.032(2) 0.031(3) 0.0080(19) O2 0.094(4) 0.123(5) 0.110(5) 0.000 0.000 -0.043(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N4 2.181(3) 2_655 ? Zn1 N4 2.181(3) . ? Zn1 N2 2.285(3) . ? Zn1 N2 2.285(3) 2_655 ? Zn1 Cl2 2.5339(10) . ? Zn1 Cl2 2.5339(10) 2_655 ? Zn2 N1 2.167(3) 2 ? Zn2 N1 2.167(3) . ? Zn2 N3 2.233(3) . ? Zn2 N3 2.233(3) 2 ? Zn2 Cl1 2.5572(10) . ? Zn2 Cl1 2.5572(10) 2 ? C7 N2 1.475(4) . ? C7 C7 1.522(6) 2_655 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C2 C3 1.371(4) . ? C2 C1 1.388(4) . ? C2 H2A 0.9300 . ? C6 N2 1.467(4) . ? C6 C3 1.499(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 N3 1.484(4) . ? C8 C9 1.511(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C3 C4 1.386(4) . ? C1 N1 1.339(4) . ? C1 H1A 0.9300 . ? C5 N1 1.335(4) . ? C5 C4 1.370(4) . ? C5 H5A 0.9300 . ? C4 H4A 0.9300 . ? C14 N3 1.481(5) . ? C14 C14 1.498(6) 2 ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C9 C10 1.392(4) . ? C9 C13 1.389(5) . ? C10 C11 1.382(4) . ? C10 H10A 0.9300 . ? C11 N4 1.338(4) . ? C11 H11A 0.9300 . ? C13 C12 1.383(4) . ? C13 H13A 0.9300 . ? C12 N4 1.341(4) . ? C12 H12A 0.9300 . ? N2 H2B 0.9100 . ? N3 H3A 0.9100 . ? 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 N4 Zn1 N4 88.63(14) 2_655 . ? N4 Zn1 N2 170.81(10) 2_655 . ? N4 Zn1 N2 96.47(9) . . ? N4 Zn1 N2 96.47(9) 2_655 2_655 ? N4 Zn1 N2 170.81(10) . 2_655 ? N2 Zn1 N2 79.54(14) . 2_655 ? N4 Zn1 Cl2 94.82(8) 2_655 . ? N4 Zn1 Cl2 88.26(7) . . ? N2 Zn1 Cl2 92.98(7) . . ? N2 Zn1 Cl2 83.71(7) 2_655 . ? N4 Zn1 Cl2 88.26(7) 2_655 2_655 ? N4 Zn1 Cl2 94.82(8) . 2_655 ? N2 Zn1 Cl2 83.71(7) . 2_655 ? N2 Zn1 Cl2 92.98(7) 2_655 2_655 ? Cl2 Zn1 Cl2 175.69(5) . 2_655 ? N1 Zn2 N1 84.68(14) 2 . ? N1 Zn2 N3 177.93(11) 2 . ? N1 Zn2 N3 96.70(9) . . ? N1 Zn2 N3 96.70(9) 2 2 ? N1 Zn2 N3 177.93(11) . 2 ? N3 Zn2 N3 81.97(15) . 2 ? N1 Zn2 Cl1 91.20(8) 2 . ? N1 Zn2 Cl1 95.19(7) . . ? N3 Zn2 Cl1 87.14(7) . . ? N3 Zn2 Cl1 86.34(7) 2 . ? N1 Zn2 Cl1 95.19(7) 2 2 ? N1 Zn2 Cl1 91.20(8) . 2 ? N3 Zn2 Cl1 86.34(7) . 2 ? N3 Zn2 Cl1 87.14(7) 2 2 ? Cl1 Zn2 Cl1 171.36(5) . 2 ? N2 C7 C7 109.9(2) . 2_655 ? N2 C7 H7A 109.7 . . ? C7 C7 H7A 109.7 2_655 . ? N2 C7 H7B 109.7 . . ? C7 C7 H7B 109.7 2_655 . ? H7A C7 H7B 108.2 . . ? C3 C2 C1 119.8(3) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? N2 C6 C3 115.5(3) . . ? N2 C6 H6A 108.4 . . ? C3 C6 H6A 108.4 . . ? N2 C6 H6B 108.4 . . ? C3 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? N3 C8 C9 114.3(3) . . ? N3 C8 H8A 108.7 . . ? C9 C8 H8A 108.7 . . ? N3 C8 H8B 108.7 . . ? C9 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C2 C3 C4 117.1(3) . . ? C2 C3 C6 123.0(3) . . ? C4 C3 C6 119.8(3) . . ? N1 C1 C2 122.5(3) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? N1 C5 C4 122.9(3) . . ? N1 C5 H5A 118.5 . . ? C4 C5 H5A 118.5 . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? N3 C14 C14 110.7(2) . 2 ? N3 C14 H14A 109.5 . . ? C14 C14 H14A 109.5 2 . ? N3 C14 H14B 109.5 . . ? C14 C14 H14B 109.5 2 . ? H14A C14 H14B 108.1 . . ? C10 C9 C13 116.9(3) . . ? C10 C9 C8 122.3(3) . . ? C13 C9 C8 120.8(3) . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? N4 C11 C10 123.0(3) . . ? N4 C11 H11A 118.5 . . ? C10 C11 H11A 118.5 . . ? C12 C13 C9 119.6(3) . . ? C12 C13 H13A 120.2 . . ? C9 C13 H13A 120.2 . . ? N4 C12 C13 123.4(3) . . ? N4 C12 H12A 118.3 . . ? C13 C12 H12A 118.3 . . ? C6 N2 C7 109.2(3) . . ? C6 N2 Zn1 126.2(2) . . ? C7 N2 Zn1 105.30(19) . . ? C6 N2 H2B 104.8 . . ? C7 N2 H2B 104.8 . . ? Zn1 N2 H2B 104.8 . . ? C14 N3 C8 108.2(2) . . ? C14 N3 Zn2 104.04(19) . . ? C8 N3 Zn2 123.5(2) . . ? C14 N3 H3A 106.7 . . ? C8 N3 H3A 106.7 . . ? Zn2 N3 H3A 106.7 . . ? C5 N1 C1 117.3(3) . . ? C5 N1 Zn2 119.5(2) . . ? C1 N1 Zn2 123.1(2) . . ? C11 N4 C12 117.1(3) . . ? C11 N4 Zn1 120.7(2) . . ? C12 N4 Zn1 121.8(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.370 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.059 data_a _database_code_depnum_ccdc_archive 'CCDC 912063' #TrackingRef '912063.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H40 Br8 N8 O2 Zn4' _chemical_formula_weight 1421.44 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.654(3) _cell_length_b 12.336(3) _cell_length_c 13.268(4) _cell_angle_alpha 62.445(13) _cell_angle_beta 77.260(17) _cell_angle_gamma 68.993(16) _cell_volume 1305.0(7) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2880 _cell_measurement_theta_min 2.2646 _cell_measurement_theta_max 27.3717 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.809 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 7.970 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5050 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Mercury2 (1x1 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10232 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.36 _reflns_number_total 5703 _reflns_number_gt 4113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.1000P)^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 geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5703 _refine_ls_number_parameters 225 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1914 _refine_ls_wR_factor_gt 0.1683 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.26552(8) 0.90072(7) -0.50659(6) 0.0458(2) Uani 1 1 d . . . Zn2 Zn 1.13596(8) 0.30943(7) -0.22873(6) 0.04566(19) Uani 1 1 d . . . Br3 Br 0.12572(9) 0.82948(7) -0.57333(7) 0.0629(2) Uani 1 1 d . . . Br4 Br 0.30892(8) 1.09835(7) -0.62786(7) 0.0641(2) Uani 1 1 d . . . Br1 Br 1.29643(9) 0.43464(8) -0.27381(7) 0.0680(2) Uani 1 1 d . . . Br2 Br 1.22749(11) 0.11405(7) -0.24622(7) 0.0719(2) Uani 1 1 d . . . N1 N 0.9508(6) 0.4273(5) -0.3181(4) 0.0473(12) Uani 1 1 d . . . C5 C 0.9380(7) 0.5500(6) -0.3895(6) 0.0516(16) Uani 1 1 d . . . H5A H 1.0160 0.5826 -0.4001 0.062 Uiso 1 1 calc R . . C4 C 0.8108(7) 0.6295(6) -0.4479(5) 0.0498(16) Uani 1 1 d . . . H4A H 0.8054 0.7136 -0.4990 0.060 Uiso 1 1 calc R . . C3 C 0.6930(7) 0.5843(6) -0.4303(6) 0.0497(15) Uani 1 1 d . . . C2 C 0.7086(7) 0.4575(7) -0.3572(7) 0.0599(18) Uani 1 1 d . . . H2A H 0.6312 0.4234 -0.3441 0.072 Uiso 1 1 calc R . . C6 C 0.5444(7) 0.6718(7) -0.4858(6) 0.0567(17) Uani 1 1 d . . . H6A H 0.5630 0.7132 -0.5678 0.068 Uiso 1 1 calc R . . H6B H 0.4796 0.6205 -0.4701 0.068 Uiso 1 1 calc R . . C1 C 0.8375(8) 0.3823(7) -0.3043(7) 0.0577(18) Uani 1 1 d . . . H1A H 0.8470 0.2965 -0.2568 0.069 Uiso 1 1 calc R . . N3 N 0.1924(5) 0.8791(5) -0.3399(5) 0.0474(13) Uani 1 1 d . . . H3A H 0.1466 0.9580 -0.3406 0.057 Uiso 1 1 calc R . . N2 N 0.4692(5) 0.7720(5) -0.4405(4) 0.0423(11) Uani 1 1 d . . . H2B H 0.5323 0.8189 -0.4573 0.051 Uiso 1 1 calc R . . C7 C 0.4399(7) 0.7167(6) -0.3162(5) 0.0446(14) Uani 1 1 d . . . H7A H 0.5324 0.6806 -0.2794 0.054 Uiso 1 1 calc R . . H7B H 0.3957 0.6486 -0.2927 0.054 Uiso 1 1 calc R . . C8 C 0.3342(7) 0.8212(6) -0.2806(6) 0.0466(14) Uani 1 1 d . . . H8A H 0.3126 0.7850 -0.1987 0.056 Uiso 1 1 calc R . . H8B H 0.3808 0.8870 -0.3005 0.056 Uiso 1 1 calc R . . C9 C 0.0868(7) 0.8028(7) -0.2886(6) 0.0511(16) Uani 1 1 d . . . H9A H 0.1324 0.7216 -0.2942 0.061 Uiso 1 1 calc R . . H9B H -0.0009 0.8476 -0.3322 0.061 Uiso 1 1 calc R . . C10 C 0.0392(7) 0.7771(6) -0.1652(6) 0.0503(15) Uani 1 1 d . . . C13 C 0.0290(12) 0.6355(8) 0.0339(7) 0.083(3) Uani 1 1 d . . . H13A H 0.0553 0.5527 0.0910 0.100 Uiso 1 1 calc R . . C12 C -0.0823(11) 0.8453(8) -0.0170(7) 0.083(3) Uani 1 1 d . . . H12A H -0.1349 0.9125 0.0035 0.100 Uiso 1 1 calc R . . C14 C 0.0779(12) 0.6549(8) -0.0778(8) 0.089(3) Uani 1 1 d . . . H14A H 0.1367 0.5860 -0.0943 0.107 Uiso 1 1 calc R . . C11 C -0.0384(11) 0.8746(8) -0.1328(7) 0.090(3) Uani 1 1 d . . . H11A H -0.0619 0.9592 -0.1869 0.108 Uiso 1 1 calc R . . N4 N -0.0534(6) 0.7300(6) 0.0625(5) 0.0538(14) Uani 1 1 d . . . O1 O 0.643(3) 0.222(2) -0.032(2) 0.206(10) Uiso 0.50 1 d PD . . O2 O 0.386(3) 0.325(3) 0.049(3) 0.235(12) Uiso 0.50 1 d PD . . 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 0.0392(4) 0.0468(4) 0.0444(4) -0.0154(3) -0.0041(3) -0.0094(3) Zn2 0.0455(4) 0.0429(4) 0.0452(4) -0.0185(3) -0.0021(3) -0.0100(3) Br3 0.0704(5) 0.0594(4) 0.0644(5) -0.0243(4) -0.0155(4) -0.0212(4) Br4 0.0538(4) 0.0584(4) 0.0720(5) -0.0124(4) -0.0096(3) -0.0250(4) Br1 0.0603(4) 0.0696(5) 0.0819(5) -0.0324(4) -0.0001(4) -0.0299(4) Br2 0.0917(6) 0.0489(4) 0.0720(5) -0.0318(4) -0.0124(4) -0.0047(4) N1 0.046(3) 0.046(3) 0.045(3) -0.017(2) -0.003(2) -0.011(2) C5 0.046(3) 0.043(4) 0.054(4) -0.015(3) -0.001(3) -0.010(3) C4 0.049(4) 0.042(4) 0.044(3) -0.008(3) -0.003(3) -0.012(3) C3 0.047(3) 0.052(4) 0.048(3) -0.029(3) -0.007(3) 0.001(3) C2 0.039(3) 0.054(4) 0.082(5) -0.025(4) -0.016(3) -0.007(3) C6 0.044(3) 0.062(4) 0.060(4) -0.033(3) -0.016(3) 0.006(3) C1 0.049(4) 0.041(4) 0.075(5) -0.018(3) -0.016(3) -0.007(3) N3 0.037(3) 0.045(3) 0.057(3) -0.025(2) 0.005(2) -0.008(2) N2 0.034(2) 0.046(3) 0.044(3) -0.019(2) -0.003(2) -0.007(2) C7 0.037(3) 0.048(4) 0.042(3) -0.015(3) -0.008(2) -0.006(3) C8 0.038(3) 0.057(4) 0.050(3) -0.031(3) -0.003(3) -0.009(3) C9 0.044(3) 0.056(4) 0.050(4) -0.022(3) -0.004(3) -0.012(3) C10 0.049(3) 0.050(4) 0.048(4) -0.022(3) 0.004(3) -0.012(3) C13 0.130(8) 0.056(5) 0.049(4) -0.020(4) 0.006(5) -0.019(5) C12 0.117(7) 0.051(5) 0.055(4) -0.023(4) 0.022(5) -0.010(5) C14 0.136(9) 0.057(5) 0.069(5) -0.037(4) 0.020(5) -0.023(5) C11 0.113(8) 0.054(5) 0.058(5) -0.016(4) 0.008(5) 0.005(5) N4 0.059(3) 0.052(3) 0.043(3) -0.018(3) 0.002(3) -0.014(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 N3 2.089(5) . ? Zn1 N2 2.095(5) . ? Zn1 Br3 2.3399(11) . ? Zn1 Br4 2.3482(12) . ? Zn2 N1 2.047(5) . ? Zn2 N4 2.061(5) 2_665 ? Zn2 Br2 2.3545(12) . ? Zn2 Br1 2.3655(12) . ? N1 C1 1.339(9) . ? N1 C5 1.340(8) . ? C5 C4 1.387(9) . ? C5 H5A 0.9300 . ? C4 C3 1.370(10) . ? C4 H4A 0.9300 . ? C3 C2 1.379(10) . ? C3 C6 1.544(9) . ? C2 C1 1.363(9) . ? C2 H2A 0.9300 . ? C6 N2 1.507(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C1 H1A 0.9300 . ? N3 C9 1.477(8) . ? N3 C8 1.502(8) . ? N3 H3A 0.9100 . ? N2 C7 1.469(8) . ? N2 H2B 0.9100 . ? C7 C8 1.527(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.511(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.372(10) . ? C10 C14 1.388(11) . ? C13 N4 1.321(10) . ? C13 C14 1.386(11) . ? C13 H13A 0.9300 . ? C12 N4 1.293(9) . ? C12 C11 1.408(11) . ? C12 H12A 0.9300 . ? C14 H14A 0.9300 . ? C11 H11A 0.9300 . ? N4 Zn2 2.061(5) 2_665 ? 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 N2 86.3(2) . . ? N3 Zn1 Br3 110.76(15) . . ? N2 Zn1 Br3 117.17(15) . . ? N3 Zn1 Br4 114.23(15) . . ? N2 Zn1 Br4 106.82(15) . . ? Br3 Zn1 Br4 117.56(5) . . ? N1 Zn2 N4 102.5(2) . 2_665 ? N1 Zn2 Br2 111.64(15) . . ? N4 Zn2 Br2 107.34(17) 2_665 . ? N1 Zn2 Br1 106.98(15) . . ? N4 Zn2 Br1 107.26(17) 2_665 . ? Br2 Zn2 Br1 119.69(5) . . ? C1 N1 C5 118.4(6) . . ? C1 N1 Zn2 119.7(4) . . ? C5 N1 Zn2 121.9(4) . . ? N1 C5 C4 121.3(6) . . ? N1 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C3 C4 C5 120.1(6) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C4 C3 C2 117.8(6) . . ? C4 C3 C6 122.0(6) . . ? C2 C3 C6 120.1(6) . . ? C1 C2 C3 119.9(7) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? N2 C6 C3 110.7(5) . . ? N2 C6 H6A 109.5 . . ? C3 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N1 C1 C2 122.4(7) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C9 N3 C8 114.7(5) . . ? C9 N3 Zn1 112.1(4) . . ? C8 N3 Zn1 103.5(3) . . ? C9 N3 H3A 108.8 . . ? C8 N3 H3A 108.8 . . ? Zn1 N3 H3A 108.8 . . ? C7 N2 C6 112.8(5) . . ? C7 N2 Zn1 105.6(3) . . ? C6 N2 Zn1 116.3(4) . . ? C7 N2 H2B 107.2 . . ? C6 N2 H2B 107.2 . . ? Zn1 N2 H2B 107.2 . . ? N2 C7 C8 109.3(5) . . ? N2 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? N3 C8 C7 109.7(5) . . ? N3 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? N3 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N3 C9 C10 113.8(6) . . ? N3 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N3 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C14 116.2(7) . . ? C11 C10 C9 121.6(6) . . ? C14 C10 C9 122.2(6) . . ? N4 C13 C14 122.6(8) . . ? N4 C13 H13A 118.7 . . ? C14 C13 H13A 118.7 . . ? N4 C12 C11 123.5(7) . . ? N4 C12 H12A 118.2 . . ? C11 C12 H12A 118.2 . . ? C13 C14 C10 120.2(8) . . ? C13 C14 H14A 119.9 . . ? C10 C14 H14A 119.9 . . ? C10 C11 C12 119.4(7) . . ? C10 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C12 N4 C13 118.0(6) . . ? C12 N4 Zn2 122.1(5) . 2_665 ? C13 N4 Zn2 120.0(5) . 2_665 ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.36 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 1.020 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.162 data_a6 _database_code_depnum_ccdc_archive 'CCDC 912064' #TrackingRef 'ZnCl-1r.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H44 Cl8 N8 O4 Zn4' _chemical_formula_weight 1101.79 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 triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.377(3) _cell_length_b 11.834(4) _cell_length_c 12.956(4) _cell_angle_alpha 64.086(10) _cell_angle_beta 79.020(14) _cell_angle_gamma 71.274(12) _cell_volume 1222.7(7) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2724 _cell_measurement_theta_min 2.5586 _cell_measurement_theta_max 27.5089 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.3500 _exptl_crystal_size_mid 0.2500 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 2.413 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9389 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Mercury70 (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13777 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5557 _reflns_number_gt 4531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0951P)^2^+1.4638P] 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 5557 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1591 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 Zn2 Zn 0.73823(5) 0.59551(5) 0.50761(4) 0.03691(17) Uani 1 1 d . . . Zn1 Zn -0.13839(6) 1.19021(5) 0.23280(4) 0.03647(17) Uani 1 1 d . . . Cl3 Cl 0.88179(16) 0.66286(12) 0.57225(11) 0.0543(3) Uani 1 1 d . . . Cl4 Cl 0.69022(14) 0.40662(12) 0.62216(11) 0.0521(3) Uani 1 1 d . . . Cl1 Cl -0.29166(15) 1.06461(14) 0.27289(13) 0.0579(3) Uani 1 1 d . . . Cl2 Cl -0.22361(18) 1.37824(12) 0.25099(12) 0.0615(4) Uani 1 1 d . . . C9 C 0.9170(5) 0.6951(5) 0.2881(4) 0.0412(10) Uani 1 1 d . . . H9A H 1.0059 0.6514 0.3326 0.049 Uiso 1 1 calc R . . H9B H 0.8725 0.7785 0.2938 0.049 Uiso 1 1 calc R . . C2 C 0.5632(5) 0.7794(4) 0.3164(4) 0.0369(9) Uani 1 1 d . . . H2A H 0.6105 0.8495 0.2931 0.044 Uiso 1 1 calc R . . H2B H 0.4688 0.8150 0.2790 0.044 Uiso 1 1 calc R . . C3 C 0.4605(5) 0.8269(5) 0.4875(4) 0.0438(10) Uani 1 1 d . . . H3A H 0.5288 0.8793 0.4736 0.053 Uiso 1 1 calc R . . H3B H 0.4411 0.7850 0.5699 0.053 Uiso 1 1 calc R . . C1 C 0.6657(5) 0.6734(5) 0.2801(4) 0.0392(9) Uani 1 1 d . . . H1A H 0.6154 0.6063 0.2987 0.047 Uiso 1 1 calc R . . H1B H 0.6877 0.7098 0.1976 0.047 Uiso 1 1 calc R . . C4 C 0.3136(5) 0.9150(4) 0.4328(4) 0.0393(9) Uani 1 1 d . . . C10 C 0.9648(5) 0.7194(5) 0.1646(4) 0.0411(10) Uani 1 1 d . . . C14 C 0.9234(8) 0.8429(5) 0.0788(5) 0.0696(18) Uani 1 1 d . . . H14A H 0.8661 0.9125 0.0973 0.083 Uiso 1 1 calc R . . C11 C 1.0441(8) 0.6207(6) 0.1312(5) 0.0723(19) Uani 1 1 d . . . H11A H 1.0708 0.5352 0.1857 0.087 Uiso 1 1 calc R . . C13 C 0.9670(8) 0.8634(5) -0.0352(5) 0.0708(18) Uani 1 1 d . . . H13A H 0.9333 0.9462 -0.0924 0.085 Uiso 1 1 calc R . . C12 C 1.0849(8) 0.6486(5) 0.0156(5) 0.0695(18) Uani 1 1 d . . . H12A H 1.1353 0.5797 -0.0058 0.083 Uiso 1 1 calc R . . C5 C 0.1895(5) 0.8679(4) 0.4487(4) 0.0426(10) Uani 1 1 d . . . H5A H 0.1934 0.7817 0.4979 0.051 Uiso 1 1 calc R . . C8 C 0.2978(6) 1.0449(5) 0.3614(5) 0.0492(11) Uani 1 1 d . . . H8A H 0.3771 1.0813 0.3495 0.059 Uiso 1 1 calc R . . C6 C 0.0618(5) 0.9480(4) 0.3921(4) 0.0398(9) Uani 1 1 d . . . H6A H -0.0193 0.9139 0.4035 0.048 Uiso 1 1 calc R . . C7 C 0.1663(6) 1.1206(5) 0.3080(4) 0.0481(11) Uani 1 1 d . . . H7A H 0.1584 1.2081 0.2608 0.058 Uiso 1 1 calc R . . N1 N 0.8074(4) 0.6155(3) 0.3395(3) 0.0352(7) Uani 1 1 d . . . H1C H 0.8512 0.5350 0.3392 0.042 Uiso 1 1 calc R . . N2 N 0.5336(4) 0.7254(3) 0.4422(3) 0.0350(7) Uani 1 1 d . . . H2C H 0.4678 0.6768 0.4583 0.042 Uiso 1 1 calc R . . N4 N 1.0555(5) 0.7681(4) -0.0652(3) 0.0452(9) Uani 1 1 d . . . N3 N 0.0481(4) 1.0736(3) 0.3211(3) 0.0366(8) Uani 1 1 d . . . O2 O 0.396(3) 1.253(3) 0.0290(11) 0.52(2) Uani 1 1 d . . . O1 O 0.638(2) 1.180(2) -0.0620(19) 0.352(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn2 0.0319(3) 0.0369(3) 0.0347(3) -0.0102(2) -0.0033(2) -0.0056(2) Zn1 0.0361(3) 0.0339(3) 0.0354(3) -0.0131(2) -0.0013(2) -0.0062(2) Cl3 0.0621(8) 0.0500(7) 0.0566(7) -0.0209(6) -0.0146(6) -0.0173(6) Cl4 0.0453(7) 0.0467(6) 0.0561(7) -0.0069(5) -0.0060(5) -0.0201(5) Cl1 0.0525(7) 0.0578(7) 0.0688(8) -0.0236(6) -0.0006(6) -0.0263(6) Cl2 0.0795(10) 0.0399(6) 0.0620(8) -0.0262(6) -0.0109(7) -0.0002(6) C9 0.035(2) 0.051(3) 0.037(2) -0.0164(19) 0.0004(17) -0.014(2) C2 0.033(2) 0.037(2) 0.034(2) -0.0111(17) -0.0023(16) -0.0050(17) C3 0.037(2) 0.051(3) 0.043(2) -0.025(2) -0.0058(19) 0.000(2) C1 0.031(2) 0.049(2) 0.042(2) -0.024(2) 0.0007(17) -0.0097(19) C4 0.037(2) 0.040(2) 0.043(2) -0.0258(19) 0.0002(18) -0.0003(18) C10 0.037(2) 0.046(2) 0.038(2) -0.0148(19) 0.0007(18) -0.0133(19) C14 0.102(5) 0.045(3) 0.053(3) -0.024(2) 0.021(3) -0.016(3) C11 0.096(5) 0.045(3) 0.045(3) -0.011(2) 0.014(3) 0.001(3) C13 0.102(5) 0.043(3) 0.045(3) -0.011(2) 0.009(3) -0.008(3) C12 0.098(5) 0.042(3) 0.045(3) -0.017(2) 0.018(3) -0.003(3) C5 0.039(2) 0.036(2) 0.043(2) -0.0121(18) 0.0024(19) -0.0057(19) C8 0.039(3) 0.046(3) 0.065(3) -0.022(2) -0.006(2) -0.011(2) C6 0.033(2) 0.039(2) 0.042(2) -0.0133(18) 0.0003(18) -0.0085(18) C7 0.049(3) 0.034(2) 0.060(3) -0.016(2) -0.007(2) -0.012(2) N1 0.0266(17) 0.0372(18) 0.0407(19) -0.0181(15) 0.0026(14) -0.0064(14) N2 0.0282(17) 0.0352(17) 0.0368(18) -0.0141(14) -0.0018(14) -0.0031(14) N4 0.054(2) 0.038(2) 0.0359(19) -0.0120(15) 0.0042(17) -0.0111(18) N3 0.0322(18) 0.0350(18) 0.0401(19) -0.0177(15) -0.0016(15) -0.0026(14) O2 0.60(4) 0.84(5) 0.108(9) 0.014(17) -0.099(15) -0.44(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 Zn2 N1 2.081(4) . ? Zn2 N2 2.086(3) . ? Zn2 Cl3 2.2024(14) . ? Zn2 Cl4 2.2123(14) . ? Zn1 N3 2.026(4) . ? Zn1 N4 2.056(4) 2_675 ? Zn1 Cl2 2.2115(14) . ? Zn1 Cl1 2.2265(14) . ? C9 N1 1.483(6) . ? C9 C10 1.500(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C2 N2 1.474(5) . ? C2 C1 1.513(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N2 1.480(6) . ? C3 C4 1.513(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C1 N1 1.474(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C4 C8 1.380(7) . ? C4 C5 1.391(7) . ? C10 C14 1.379(7) . ? C10 C11 1.366(7) . ? C14 C13 1.389(8) . ? C14 H14A 0.9300 . ? C11 C12 1.389(8) . ? C11 H11A 0.9300 . ? C13 N4 1.331(7) . ? C13 H13A 0.9300 . ? C12 N4 1.319(6) . ? C12 H12A 0.9300 . ? C5 C6 1.367(6) . ? C5 H5A 0.9300 . ? C8 C7 1.370(7) . ? C8 H8A 0.9300 . ? C6 N3 1.341(5) . ? C6 H6A 0.9300 . ? C7 N3 1.346(6) . ? C7 H7A 0.9300 . ? N1 H1C 0.9100 . ? N2 H2C 0.9100 . ? N4 Zn1 2.056(4) 2_675 ? 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 Zn2 N2 86.29(14) . . ? N1 Zn2 Cl3 110.71(11) . . ? N2 Zn2 Cl3 117.92(11) . . ? N1 Zn2 Cl4 114.41(11) . . ? N2 Zn2 Cl4 106.62(11) . . ? Cl3 Zn2 Cl4 117.08(6) . . ? N3 Zn1 N4 102.06(16) . 2_675 ? N3 Zn1 Cl2 112.61(11) . . ? N4 Zn1 Cl2 106.64(12) 2_675 . ? N3 Zn1 Cl1 106.23(11) . . ? N4 Zn1 Cl1 107.57(13) 2_675 . ? Cl2 Zn1 Cl1 120.15(6) . . ? N1 C9 C10 114.3(4) . . ? N1 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? N1 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? N2 C2 C1 109.8(3) . . ? N2 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? N2 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? N2 C3 C4 112.5(4) . . ? N2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? N2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? N1 C1 C2 110.2(3) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? C8 C4 C5 116.7(4) . . ? C8 C4 C3 121.7(4) . . ? C5 C4 C3 121.5(4) . . ? C14 C10 C11 117.0(5) . . ? C14 C10 C9 120.8(4) . . ? C11 C10 C9 122.1(4) . . ? C10 C14 C13 120.1(5) . . ? C10 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C12 C11 C10 119.7(5) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? N4 C13 C14 122.0(5) . . ? N4 C13 H13A 119.0 . . ? C14 C13 H13A 119.0 . . ? N4 C12 C11 123.1(5) . . ? N4 C12 H12A 118.5 . . ? C11 C12 H12A 118.5 . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C7 C8 C4 120.5(5) . . ? C7 C8 H8A 119.8 . . ? C4 C8 H8A 119.8 . . ? N3 C6 C5 123.0(4) . . ? N3 C6 H6A 118.5 . . ? C5 C6 H6A 118.5 . . ? N3 C7 C8 122.6(4) . . ? N3 C7 H7A 118.7 . . ? C8 C7 H7A 118.7 . . ? C1 N1 C9 113.8(3) . . ? C1 N1 Zn2 104.0(2) . . ? C9 N1 Zn2 111.7(3) . . ? C1 N1 H1C 109.0 . . ? C9 N1 H1C 109.0 . . ? Zn2 N1 H1C 109.0 . . ? C2 N2 C3 113.2(3) . . ? C2 N2 Zn2 105.0(2) . . ? C3 N2 Zn2 117.6(3) . . ? C2 N2 H2C 106.8 . . ? C3 N2 H2C 106.8 . . ? Zn2 N2 H2C 106.8 . . ? C12 N4 C13 117.5(4) . . ? C12 N4 Zn1 122.5(3) . 2_675 ? C13 N4 Zn1 120.0(3) . 2_675 ? C6 N3 C7 117.1(4) . . ? C6 N3 Zn1 122.9(3) . . ? C7 N3 Zn1 120.0(3) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.160 _refine_diff_density_min -0.528 _refine_diff_density_rms 0.125