# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Shi Bai' _publ_contact_author_email andyhor@nus.edu.sg _publ_section_title ; Zinc, Cobalt and Copper Coordination Polymers with Different Structural Motifs from Picolyl-Triazole Hybrid Ligands ; loop_ _publ_author_name S.Bai A.M.Dong J.J.Hu D.Young X.H.Zhang Yu.Zong J.Xu J.-L.Zuo A.Hor #===end data_9258 _database_code_depnum_ccdc_archive 'CCDC 751942' #TrackingRef '- CEC-CIF-29Jun2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 Cu2 I2 N4' _chemical_formula_weight 625.22 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 22.5410(6) _cell_length_b 22.5410(6) _cell_length_c 14.6276(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7432.2(4) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8443 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.53 _exptl_crystal_description ROD _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 2.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4736 _exptl_absorpt_coefficient_mu 5.613 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1822 _exptl_absorpt_correction_T_max 0.7294 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26073 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4256 _reflns_number_gt 3820 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0472P)^2^+16.3030P] 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 4256 _refine_ls_number_parameters 218 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C15 C 0.6180(13) 0.4702(8) 0.0317(7) 0.050 Uiso 0.369(9) 1 d PD A 2 H15A H 0.6463 0.4975 0.0047 0.060 Uiso 0.369(9) 1 calc PR A 2 H15B H 0.5784 0.4861 0.0226 0.060 Uiso 0.369(9) 1 calc PR A 2 C16 C 0.6230(7) 0.4100(7) -0.0139(12) 0.070 Uiso 0.369(9) 1 d PD A 2 H16A H 0.6238 0.4161 -0.0795 0.084 Uiso 0.369(9) 1 calc PR A 2 H16B H 0.6609 0.3928 0.0033 0.084 Uiso 0.369(9) 1 calc PR A 2 C17 C 0.5752(8) 0.3653(9) 0.0071(14) 0.080 Uiso 0.369(9) 1 d PD A 2 H17A H 0.5775 0.3548 0.0714 0.096 Uiso 0.369(9) 1 calc PR A 2 H17B H 0.5827 0.3296 -0.0280 0.096 Uiso 0.369(9) 1 calc PR A 2 C18 C 0.5128(10) 0.3869(11) -0.014(2) 0.090 Uiso 0.369(9) 1 d PD A 2 H18A H 0.5128 0.4065 -0.0727 0.108 Uiso 0.369(9) 1 calc PR A 2 H18B H 0.5012 0.4158 0.0320 0.108 Uiso 0.369(9) 1 calc PR A 2 C19 C 0.4674(9) 0.3367(12) -0.015(3) 0.090 Uiso 0.369(9) 1 d PD A 2 H19A H 0.4727 0.3138 -0.0705 0.108 Uiso 0.369(9) 1 calc PR A 2 H19B H 0.4749 0.3106 0.0364 0.108 Uiso 0.369(9) 1 calc PR A 2 C20 C 0.4042(10) 0.3582(11) -0.0105(18) 0.090 Uiso 0.369(9) 1 d PD A 2 H20A H 0.3778 0.3249 -0.0150 0.135 Uiso 0.369(9) 1 calc PR A 2 H20B H 0.3968 0.3851 -0.0601 0.135 Uiso 0.369(9) 1 calc PR A 2 H20C H 0.3978 0.3782 0.0466 0.135 Uiso 0.369(9) 1 calc PR A 2 C9 C 0.6281(4) 0.4613(5) 0.0299(4) 0.047(3) Uani 0.631(9) 1 d PDU A 1 H9A H 0.6533 0.4293 0.0083 0.056 Uiso 0.631(9) 1 calc PR A 1 H9B H 0.6432 0.4982 0.0050 0.056 Uiso 0.631(9) 1 calc PR A 1 C10 C 0.5654(4) 0.4513(5) -0.0032(6) 0.083(3) Uani 0.631(9) 1 d PDU A 1 H10A H 0.5393 0.4769 0.0319 0.099 Uiso 0.631(9) 1 calc PR A 1 H10B H 0.5631 0.4642 -0.0664 0.099 Uiso 0.631(9) 1 calc PR A 1 C11 C 0.5421(6) 0.3902(5) 0.0021(7) 0.084(4) Uani 0.631(9) 1 d PDU A 1 H11A H 0.5530 0.3734 0.0608 0.101 Uiso 0.631(9) 1 calc PR A 1 H11B H 0.5609 0.3665 -0.0450 0.101 Uiso 0.631(9) 1 calc PR A 1 C12 C 0.4744(6) 0.3855(5) -0.0091(9) 0.094(4) Uani 0.631(9) 1 d PDU A 1 H12A H 0.4553 0.4062 0.0411 0.113 Uiso 0.631(9) 1 calc PR A 1 H12B H 0.4629 0.4051 -0.0654 0.113 Uiso 0.631(9) 1 calc PR A 1 C13 C 0.4519(6) 0.3214(5) -0.0114(9) 0.087(4) Uani 0.631(9) 1 d PDU A 1 H13A H 0.4658 0.3018 -0.0664 0.104 Uiso 0.631(9) 1 calc PR A 1 H13B H 0.4670 0.2998 0.0411 0.104 Uiso 0.631(9) 1 calc PR A 1 C14 C 0.3859(6) 0.3222(9) -0.0096(9) 0.114(5) Uani 0.631(9) 1 d PDU A 1 H14A H 0.3712 0.2822 -0.0066 0.172 Uiso 0.631(9) 1 calc PR A 1 H14B H 0.3713 0.3409 -0.0641 0.172 Uiso 0.631(9) 1 calc PR A 1 H14C H 0.3725 0.3439 0.0429 0.172 Uiso 0.631(9) 1 calc PR A 1 Cu1 Cu 0.52301(2) 0.68993(2) 0.56760(3) 0.03894(13) Uani 1 1 d . . . Cu2 Cu 0.73866(2) 0.48635(2) 0.36740(3) 0.04070(13) Uani 1 1 d . . . I1 I 0.586494(11) 0.781675(12) 0.504861(16) 0.03562(9) Uani 1 1 d . . . I2 I 0.735010(14) 0.416601(12) 0.511810(19) 0.04330(10) Uani 1 1 d . . . N1 N 0.54404(17) 0.61222(16) 0.5051(2) 0.0384(8) Uani 1 1 d . . . N2 N 0.61616(14) 0.45699(14) 0.2779(2) 0.0322(7) Uani 1 1 d . . . N3 N 0.67394(14) 0.46939(14) 0.2658(2) 0.0320(7) Uani 1 1 d . . . N4 N 0.68208(15) 0.47333(14) 0.1760(2) 0.0340(7) Uani 1 1 d . A . C1 C 0.5355(3) 0.6048(2) 0.4152(3) 0.0610(14) Uani 1 1 d . . . H1 H 0.5189 0.6360 0.3823 0.073 Uiso 1 1 calc R . . C2 C 0.5497(3) 0.5538(2) 0.3688(3) 0.0597(14) Uani 1 1 d . . . H2 H 0.5422 0.5509 0.3065 0.072 Uiso 1 1 calc R . . C3 C 0.57511(17) 0.50695(17) 0.4148(3) 0.0343(8) Uani 1 1 d . . . C4 C 0.58439(18) 0.51365(19) 0.5071(3) 0.0359(8) Uani 1 1 d . . . H4 H 0.6014 0.4831 0.5409 0.043 Uiso 1 1 calc R . . C5 C 0.56813(17) 0.56649(18) 0.5497(3) 0.0365(8) Uani 1 1 d . . . H5 H 0.5744 0.5701 0.6123 0.044 Uiso 1 1 calc R . . C6 C 0.59172(18) 0.44913(17) 0.3691(3) 0.0357(8) Uani 1 1 d . . . H6A H 0.6207 0.4287 0.4068 0.043 Uiso 1 1 calc R . . H6B H 0.5568 0.4242 0.3653 0.043 Uiso 1 1 calc R . . C7 C 0.58765(19) 0.4534(2) 0.1980(3) 0.0418(9) Uani 1 1 d . A . H7 H 0.5476 0.4455 0.1887 0.050 Uiso 1 1 calc R . . C8 C 0.63025(19) 0.46365(19) 0.1324(3) 0.0393(9) Uani 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 C9 0.034(5) 0.078(7) 0.028(3) -0.004(3) -0.001(3) -0.009(4) C10 0.057(6) 0.143(10) 0.049(5) -0.012(5) -0.011(4) -0.002(6) C11 0.108(10) 0.092(8) 0.052(5) -0.009(5) -0.008(6) 0.017(8) C12 0.100(9) 0.100(9) 0.081(7) 0.008(6) -0.009(7) -0.009(7) C13 0.090(9) 0.129(11) 0.041(5) -0.008(6) 0.005(6) 0.003(7) C14 0.117(11) 0.156(14) 0.070(7) 0.003(9) -0.001(7) 0.027(10) Cu1 0.0436(3) 0.0362(3) 0.0371(3) -0.0056(2) 0.0010(2) 0.0035(2) Cu2 0.0479(3) 0.0411(3) 0.0331(3) -0.0046(2) 0.0018(2) 0.0000(2) I1 0.03403(14) 0.04196(15) 0.03086(14) 0.00211(10) 0.00211(9) 0.00042(10) I2 0.05524(19) 0.03683(16) 0.03784(16) -0.00004(11) -0.00762(12) -0.00025(12) N1 0.044(2) 0.0372(18) 0.0337(17) -0.0039(14) 0.0015(14) 0.0040(15) N2 0.0365(17) 0.0298(16) 0.0303(15) -0.0046(12) 0.0047(13) -0.0012(13) N3 0.0343(16) 0.0304(16) 0.0314(16) -0.0015(12) 0.0019(13) 0.0001(13) N4 0.0365(17) 0.0350(17) 0.0304(15) -0.0023(13) 0.0017(13) -0.0020(13) C1 0.098(4) 0.049(3) 0.036(2) -0.001(2) -0.008(2) 0.028(3) C2 0.099(4) 0.049(3) 0.030(2) -0.0060(19) -0.008(2) 0.027(3) C3 0.0327(19) 0.035(2) 0.0348(19) -0.0028(15) 0.0055(15) -0.0025(15) C4 0.034(2) 0.037(2) 0.036(2) -0.0021(16) 0.0003(15) 0.0049(16) C5 0.034(2) 0.041(2) 0.034(2) -0.0076(16) -0.0021(15) 0.0054(16) C6 0.042(2) 0.034(2) 0.0311(18) -0.0021(15) 0.0071(16) -0.0032(16) C7 0.037(2) 0.053(3) 0.035(2) -0.0065(18) -0.0025(17) -0.0067(18) C8 0.041(2) 0.045(2) 0.031(2) -0.0027(17) -0.0002(16) -0.0061(17) _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 C15 C8 1.506(10) . ? C15 C16 1.517(10) . ? C16 C17 1.508(10) . ? C17 C18 1.518(10) . ? C18 C19 1.525(10) . ? C19 C20 1.506(10) . ? C9 C8 1.501(7) . ? C9 C10 1.512(8) . ? C10 C11 1.477(9) . ? C11 C12 1.539(9) . ? C12 C13 1.531(9) . ? C13 C14 1.490(9) . ? Cu1 N1 2.032(3) . ? Cu1 Cu1 2.6505(8) 12_767 ? Cu1 Cu1 2.6505(8) 15_566 ? Cu1 I1 2.6716(6) 15_566 ? Cu1 I1 2.6771(6) . ? Cu1 I1 2.7100(6) 6_564 ? Cu1 Cu1 2.9000(10) 6_564 ? Cu2 N4 2.058(3) 8_454 ? Cu2 N3 2.118(3) . ? Cu2 I2 2.6346(6) . ? Cu2 I2 2.6356(6) 7_544 ? I1 Cu1 2.6716(6) 12_767 ? I1 Cu1 2.7100(6) 6_564 ? I2 Cu2 2.6356(6) 8_454 ? N1 C5 1.335(5) . ? N1 C1 1.340(5) . ? N2 C7 1.336(5) . ? N2 N3 1.344(4) . ? N2 C6 1.455(5) . ? N3 N4 1.328(4) . ? N4 C8 1.349(5) . ? N4 Cu2 2.058(3) 7_544 ? C1 C2 1.373(6) . ? C2 C3 1.377(6) . ? C3 C4 1.375(5) . ? C3 C6 1.511(5) . ? C4 C5 1.393(5) . ? C7 C8 1.377(6) . ? 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 C8 C15 C16 109.2(12) . . ? C17 C16 C15 117.1(17) . . ? C16 C17 C18 114.0(17) . . ? C17 C18 C19 112.7(17) . . ? C20 C19 C18 113(2) . . ? C8 C9 C10 110.8(7) . . ? C11 C10 C9 117.0(10) . . ? C10 C11 C12 114.3(10) . . ? C13 C12 C11 113.3(10) . . ? C14 C13 C12 108.6(12) . . ? N1 Cu1 Cu1 145.15(11) . 12_767 ? N1 Cu1 Cu1 136.19(11) . 15_566 ? Cu1 Cu1 Cu1 66.33(2) 12_767 15_566 ? N1 Cu1 I1 103.19(10) . 15_566 ? Cu1 Cu1 I1 61.22(2) 12_767 15_566 ? Cu1 Cu1 I1 60.40(2) 15_566 15_566 ? N1 Cu1 I1 112.77(10) . . ? Cu1 Cu1 I1 60.191(17) 12_767 . ? Cu1 Cu1 I1 110.573(17) 15_566 . ? I1 Cu1 I1 117.80(2) 15_566 . ? N1 Cu1 I1 105.29(11) . 6_564 ? Cu1 Cu1 I1 109.560(17) 12_767 6_564 ? Cu1 Cu1 I1 59.773(17) 15_566 6_564 ? I1 Cu1 I1 116.64(2) 15_566 6_564 ? I1 Cu1 I1 100.857(19) . 6_564 ? N1 Cu1 Cu1 152.68(10) . 6_564 ? Cu1 Cu1 Cu1 56.836(11) 12_767 6_564 ? Cu1 Cu1 Cu1 56.836(11) 15_566 6_564 ? I1 Cu1 Cu1 103.554(12) 15_566 6_564 ? I1 Cu1 Cu1 57.981(17) . 6_564 ? I1 Cu1 Cu1 56.885(17) 6_564 6_564 ? N4 Cu2 N3 109.77(13) 8_454 . ? N4 Cu2 I2 101.17(9) 8_454 . ? N3 Cu2 I2 115.69(9) . . ? N4 Cu2 I2 112.99(9) 8_454 7_544 ? N3 Cu2 I2 98.32(9) . 7_544 ? I2 Cu2 I2 119.23(2) . 7_544 ? Cu1 I1 Cu1 59.411(18) 12_767 . ? Cu1 I1 Cu1 59.008(18) 12_767 6_564 ? Cu1 I1 Cu1 65.136(19) . 6_564 ? Cu2 I2 Cu2 89.197(15) . 8_454 ? C5 N1 C1 116.2(4) . . ? C5 N1 Cu1 122.7(3) . . ? C1 N1 Cu1 121.0(3) . . ? C7 N2 N3 111.3(3) . . ? C7 N2 C6 127.8(3) . . ? N3 N2 C6 120.9(3) . . ? N4 N3 N2 106.1(3) . . ? N4 N3 Cu2 125.9(2) . . ? N2 N3 Cu2 127.8(2) . . ? N3 N4 C8 109.7(3) . . ? N3 N4 Cu2 123.1(3) . 7_544 ? C8 N4 Cu2 127.2(3) . 7_544 ? N1 C1 C2 123.8(4) . . ? C1 C2 C3 119.9(4) . . ? C4 C3 C2 117.3(4) . . ? C4 C3 C6 119.4(4) . . ? C2 C3 C6 123.3(4) . . ? C3 C4 C5 119.5(4) . . ? N1 C5 C4 123.3(4) . . ? N2 C6 C3 113.2(3) . . ? N2 C7 C8 105.3(4) . . ? N4 C8 C7 107.6(3) . . ? N4 C8 C9 120.4(5) . . ? C7 C8 C9 131.9(5) . . ? N4 C8 C15 127.3(12) . . ? C7 C8 C15 124.8(12) . . ? C9 C8 C15 11.7(11) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.074 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.130 #===end data_9430 _database_code_depnum_ccdc_archive 'CCDC 751943' #TrackingRef '- CEC-CIF-29Jun2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H44 Cl2 Co N8 O12' _chemical_formula_weight 790.52 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1710(5) _cell_length_b 9.8000(5) _cell_length_c 19.7984(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.3480(10) _cell_angle_gamma 90.00 _cell_volume 1774.28(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5887 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.47 _exptl_crystal_description BLOCK _exptl_crystal_colour PINK _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 826 _exptl_absorpt_coefficient_mu 0.703 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7200 _exptl_absorpt_correction_T_max 0.8721 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12313 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4058 _reflns_number_gt 3658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0532P)^2^+1.0753P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4058 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 0.5000 0.0000 0.01322(10) Uani 1 2 d S . . N1 N 0.39899(15) 0.54301(15) 0.09147(7) 0.0156(3) Uani 1 1 d . . . N2 N 0.28302(15) 0.62323(15) 0.08399(7) 0.0168(3) Uani 1 1 d . . . N3 N 0.23424(15) 0.63675(15) 0.14533(7) 0.0161(3) Uani 1 1 d . . . N4 N -0.29189(15) 0.57131(15) 0.04907(7) 0.0154(3) Uani 1 1 d . . . C1 C 0.42433(19) 0.50632(17) 0.15768(9) 0.0166(3) Uani 1 1 d . . . C2 C 0.31747(19) 0.56662(18) 0.19248(9) 0.0178(3) Uani 1 1 d . . . H2 H 0.3049 0.5603 0.2396 0.021 Uiso 1 1 calc R . . C3 C 0.10636(19) 0.72143(19) 0.15329(10) 0.0199(4) Uani 1 1 d . . . H3A H 0.1252 0.8144 0.1364 0.024 Uiso 1 1 calc R . . H3B H 0.0906 0.7287 0.2021 0.024 Uiso 1 1 calc R . . C4 C -0.27831(19) 0.70016(18) 0.07201(9) 0.0170(3) Uani 1 1 d . . . H4 H -0.3606 0.7589 0.0657 0.020 Uiso 1 1 calc R . . C5 C -0.15120(19) 0.75172(18) 0.10422(9) 0.0168(3) Uani 1 1 d . . . H5 H -0.1459 0.8444 0.1182 0.020 Uiso 1 1 calc R . . C6 C -0.03108(18) 0.66598(17) 0.11591(8) 0.0156(3) Uani 1 1 d . . . C7 C -0.04410(19) 0.53239(18) 0.09303(9) 0.0167(3) Uani 1 1 d . . . H7 H 0.0355 0.4707 0.1002 0.020 Uiso 1 1 calc R . . C8 C -0.17423(19) 0.48986(17) 0.05962(9) 0.0171(3) Uani 1 1 d . . . H8 H -0.1808 0.3987 0.0433 0.020 Uiso 1 1 calc R . . C9 C 0.55006(19) 0.41966(18) 0.18418(9) 0.0186(3) Uani 1 1 d . . . H9A H 0.5992 0.3818 0.1455 0.022 Uiso 1 1 calc R . . H9B H 0.5124 0.3421 0.2098 0.022 Uiso 1 1 calc R . . C10 C 0.6621(2) 0.49804(18) 0.23022(10) 0.0206(4) Uani 1 1 d . . . H10A H 0.6924 0.5810 0.2065 0.025 Uiso 1 1 calc R . . H10B H 0.6163 0.5272 0.2716 0.025 Uiso 1 1 calc R . . C11 C 0.79658(19) 0.41149(18) 0.25030(9) 0.0186(3) Uani 1 1 d . . . H11A H 0.7654 0.3279 0.2733 0.022 Uiso 1 1 calc R . . H11B H 0.8421 0.3831 0.2088 0.022 Uiso 1 1 calc R . . C12 C 0.9104(2) 0.4854(2) 0.29685(11) 0.0261(4) Uani 1 1 d . . . H12A H 0.8666 0.5108 0.3393 0.031 Uiso 1 1 calc R . . H12B H 0.9400 0.5704 0.2746 0.031 Uiso 1 1 calc R . . C13 C 1.0452(2) 0.3973(2) 0.31385(11) 0.0294(4) Uani 1 1 d . . . H13A H 1.0163 0.3131 0.3360 0.044 Uiso 1 1 calc R . . H13B H 1.1151 0.4476 0.3444 0.044 Uiso 1 1 calc R . . H13C H 1.0908 0.3745 0.2721 0.044 Uiso 1 1 calc R . . Cl1 Cl 0.15697(5) 0.16421(4) 0.10056(2) 0.02082(12) Uani 1 1 d . . . O1 O 0.04617(17) 0.22328(16) 0.05422(8) 0.0332(3) Uani 1 1 d . . . O2 O 0.20183(19) 0.26034(19) 0.15223(9) 0.0435(4) Uani 1 1 d . . . O3 O 0.28269(16) 0.12703(15) 0.06396(7) 0.0294(3) Uani 1 1 d . . . O4 O 0.10057(17) 0.04462(16) 0.13104(9) 0.0351(4) Uani 1 1 d . . . O1W O 0.53706(15) 0.29559(14) 0.03234(7) 0.0186(3) Uani 1 1 d . . . H1WA H 0.472(3) 0.254(3) 0.0496(13) 0.031(7) Uiso 1 1 d . . . H1WB H 0.601(4) 0.241(3) 0.0268(15) 0.050(9) Uiso 1 1 d . . . O2W O 0.75049(18) 0.10346(17) 0.03182(9) 0.0333(4) Uani 1 1 d . . . H2WA H 0.838(4) 0.134(4) 0.0376(16) 0.062(10) Uiso 1 1 d . . . H2WB H 0.749(4) 0.045(4) 0.0023(18) 0.060(10) 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 Co1 0.00907(16) 0.01533(17) 0.01555(17) 0.00016(11) 0.00292(12) 0.00112(11) N1 0.0109(6) 0.0168(7) 0.0193(7) -0.0003(6) 0.0027(5) 0.0003(5) N2 0.0120(7) 0.0198(7) 0.0189(7) -0.0024(6) 0.0038(5) 0.0012(5) N3 0.0120(7) 0.0187(7) 0.0182(7) -0.0038(6) 0.0043(5) -0.0021(5) N4 0.0123(7) 0.0178(7) 0.0166(7) 0.0005(5) 0.0046(5) 0.0001(5) C1 0.0154(8) 0.0169(8) 0.0177(8) -0.0004(6) 0.0025(6) -0.0033(6) C2 0.0155(8) 0.0212(9) 0.0170(8) -0.0011(6) 0.0031(6) -0.0029(7) C3 0.0124(8) 0.0211(9) 0.0266(9) -0.0091(7) 0.0036(7) 0.0004(7) C4 0.0138(8) 0.0192(8) 0.0184(8) 0.0006(7) 0.0042(6) 0.0042(6) C5 0.0171(8) 0.0159(8) 0.0179(8) -0.0014(6) 0.0055(6) 0.0007(6) C6 0.0116(8) 0.0193(8) 0.0166(8) -0.0013(6) 0.0055(6) -0.0014(6) C7 0.0121(8) 0.0179(8) 0.0206(8) -0.0005(7) 0.0034(6) 0.0021(6) C8 0.0149(8) 0.0157(8) 0.0208(8) -0.0011(6) 0.0034(7) 0.0001(6) C9 0.0188(8) 0.0176(8) 0.0193(8) 0.0037(7) 0.0013(6) 0.0014(7) C10 0.0184(9) 0.0205(9) 0.0228(9) 0.0010(7) 0.0003(7) 0.0024(7) C11 0.0174(8) 0.0194(8) 0.0191(8) 0.0032(7) 0.0026(6) 0.0012(7) C12 0.0207(9) 0.0232(10) 0.0337(11) -0.0010(8) -0.0030(8) 0.0011(7) C13 0.0191(9) 0.0303(11) 0.0380(11) 0.0004(9) -0.0030(8) 0.0024(8) Cl1 0.0205(2) 0.0167(2) 0.0259(2) 0.00126(16) 0.00613(17) -0.00023(15) O1 0.0287(8) 0.0337(8) 0.0376(8) 0.0081(6) 0.0043(6) 0.0102(6) O2 0.0413(10) 0.0432(10) 0.0462(10) -0.0168(8) 0.0054(8) -0.0078(8) O3 0.0236(7) 0.0312(8) 0.0350(8) 0.0042(6) 0.0123(6) 0.0033(6) O4 0.0301(8) 0.0250(7) 0.0520(10) 0.0114(7) 0.0147(7) -0.0005(6) O1W 0.0139(6) 0.0180(6) 0.0245(7) 0.0019(5) 0.0050(5) 0.0020(5) O2W 0.0241(8) 0.0280(8) 0.0483(10) -0.0028(7) 0.0066(7) 0.0058(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1W 2.1226(13) . ? Co1 O1W 2.1226(13) 3_665 ? Co1 N1 2.1378(14) . ? Co1 N1 2.1378(14) 3_665 ? Co1 N4 2.1895(14) 1_655 ? Co1 N4 2.1895(14) 3_565 ? N1 N2 1.322(2) . ? N1 C1 1.362(2) . ? N2 N3 1.332(2) . ? N3 C2 1.348(2) . ? N3 C3 1.455(2) . ? N4 C4 1.344(2) . ? N4 C8 1.346(2) . ? N4 Co1 2.1895(14) 1_455 ? C1 C2 1.373(2) . ? C1 C9 1.495(2) . ? C3 C6 1.513(2) . ? C4 C5 1.381(2) . ? C5 C6 1.391(2) . ? C6 C7 1.387(2) . ? C7 C8 1.384(2) . ? C9 C10 1.528(2) . ? C10 C11 1.525(2) . ? C11 C12 1.522(3) . ? C12 C13 1.524(3) . ? Cl1 O2 1.4282(17) . ? Cl1 O4 1.4327(15) . ? Cl1 O1 1.4380(15) . ? Cl1 O3 1.4538(14) . ? 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 O1W Co1 O1W 180.0 . 3_665 ? O1W Co1 N1 90.02(5) . . ? O1W Co1 N1 89.98(5) 3_665 . ? O1W Co1 N1 89.98(5) . 3_665 ? O1W Co1 N1 90.02(5) 3_665 3_665 ? N1 Co1 N1 180.0 . 3_665 ? O1W Co1 N4 93.05(5) . 1_655 ? O1W Co1 N4 86.96(5) 3_665 1_655 ? N1 Co1 N4 88.87(5) . 1_655 ? N1 Co1 N4 91.13(5) 3_665 1_655 ? O1W Co1 N4 86.95(5) . 3_565 ? O1W Co1 N4 93.04(5) 3_665 3_565 ? N1 Co1 N4 91.13(5) . 3_565 ? N1 Co1 N4 88.87(5) 3_665 3_565 ? N4 Co1 N4 180.0 1_655 3_565 ? N2 N1 C1 110.00(14) . . ? N2 N1 Co1 114.77(11) . . ? C1 N1 Co1 135.23(12) . . ? N1 N2 N3 106.25(13) . . ? N2 N3 C2 111.64(14) . . ? N2 N3 C3 118.98(14) . . ? C2 N3 C3 129.37(15) . . ? C4 N4 C8 116.87(15) . . ? C4 N4 Co1 120.33(11) . 1_455 ? C8 N4 Co1 122.77(12) . 1_455 ? N1 C1 C2 107.03(16) . . ? N1 C1 C9 123.96(16) . . ? C2 C1 C9 128.99(16) . . ? N3 C2 C1 105.08(15) . . ? N3 C3 C6 112.99(14) . . ? N4 C4 C5 123.56(16) . . ? C4 C5 C6 119.06(16) . . ? C7 C6 C5 117.92(16) . . ? C7 C6 C3 123.11(15) . . ? C5 C6 C3 118.96(15) . . ? C8 C7 C6 119.33(16) . . ? N4 C8 C7 123.21(16) . . ? C1 C9 C10 112.93(15) . . ? C11 C10 C9 111.71(15) . . ? C12 C11 C10 113.42(15) . . ? C11 C12 C13 111.83(16) . . ? O2 Cl1 O4 109.36(11) . . ? O2 Cl1 O1 110.04(10) . . ? O4 Cl1 O1 109.74(10) . . ? O2 Cl1 O3 109.03(10) . . ? O4 Cl1 O3 109.28(9) . . ? O1 Cl1 O3 109.38(9) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O3 0.82(3) 2.17(3) 2.964(2) 163(2) . O1W H1WB O2W 0.81(3) 1.92(3) 2.717(2) 169(3) . O2W H2WA O1 0.85(4) 2.10(4) 2.957(2) 176(3) 1_655 O2W H2WB O3 0.82(4) 2.14(4) 2.950(2) 170(3) 3_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.701 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.075 # Attachment '- CEC-CIF-29Jun2011.cif' data_9483 _database_code_depnum_ccdc_archive 'CCDC 751944' #TrackingRef '- CEC-CIF-29Jun2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Cl2 N4 Zn' _chemical_formula_weight 352.56 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' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.4667(6) _cell_length_b 9.3666(5) _cell_length_c 14.1959(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.6200(10) _cell_angle_gamma 90.00 _cell_volume 1530.15(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6285 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 1.946 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4197 _exptl_absorpt_correction_T_max 0.7724 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10502 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3497 _reflns_number_gt 3267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0394P)^2^+0.3104P] 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 3497 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0646 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.216570(13) 0.619412(18) 0.460610(12) 0.01626(7) Uani 1 1 d . . . Cl1 Cl 0.14773(3) 0.75911(4) 0.55311(3) 0.02095(9) Uani 1 1 d . . . Cl2 Cl 0.38103(3) 0.69043(4) 0.44911(3) 0.02284(9) Uani 1 1 d . . . N1 N 0.24215(11) 0.42669(14) 0.53380(9) 0.0171(2) Uani 1 1 d . . . N2 N 0.40962(10) -0.02339(13) 0.73572(9) 0.0172(2) Uani 1 1 d . . . N3 N 0.49203(10) -0.01890(14) 0.82939(9) 0.0181(2) Uani 1 1 d . . . N4 N 0.58319(10) -0.08443(14) 0.82347(9) 0.0175(2) Uani 1 1 d . . . C1 C 0.15380(13) 0.35677(17) 0.54527(11) 0.0192(3) Uani 1 1 d . . . H1 H 0.0774 0.3940 0.5130 0.023 Uiso 1 1 calc R . . C2 C 0.16948(13) 0.23286(17) 0.60209(11) 0.0192(3) Uani 1 1 d . . . H2 H 0.1049 0.1863 0.6084 0.023 Uiso 1 1 calc R . . C3 C 0.28067(12) 0.17738(15) 0.64972(10) 0.0176(3) Uani 1 1 d . . . C4 C 0.37150(13) 0.24793(16) 0.63591(12) 0.0219(3) Uani 1 1 d . . . H4 H 0.4484 0.2116 0.6659 0.026 Uiso 1 1 calc R . . C5 C 0.34932(13) 0.37143(16) 0.57819(12) 0.0215(3) Uani 1 1 d . . . H5 H 0.4123 0.4190 0.5696 0.026 Uiso 1 1 calc R . . C6 C 0.29809(12) 0.04581(16) 0.71542(11) 0.0188(3) Uani 1 1 d . . . H6A H 0.2932 0.0728 0.7811 0.023 Uiso 1 1 calc R . . H6B H 0.2348 -0.0229 0.6809 0.023 Uiso 1 1 calc R . . C7 C 0.44660(13) -0.09084(16) 0.66964(11) 0.0205(3) Uani 1 1 d . . . H7 H 0.4037 -0.1078 0.5991 0.025 Uiso 1 1 calc R . . C8 C 0.55919(13) -0.12953(15) 0.72592(11) 0.0187(3) Uani 1 1 d . . . C9 C 0.64898(13) -0.19536(17) 0.69446(12) 0.0225(3) Uani 1 1 d . . . H9A H 0.6106 -0.2429 0.6275 0.027 Uiso 1 1 calc R . . H9B H 0.6921 -0.2689 0.7449 0.027 Uiso 1 1 calc R . . C10 C 0.73434(14) -0.08288(18) 0.68662(12) 0.0233(3) Uani 1 1 d . . . H10A H 0.6914 -0.0122 0.6337 0.028 Uiso 1 1 calc R . . H10B H 0.7691 -0.0318 0.7525 0.028 Uiso 1 1 calc R . . C11 C 0.83077(15) -0.1477(2) 0.65999(13) 0.0287(4) Uani 1 1 d . . . H11A H 0.7963 -0.1910 0.5912 0.034 Uiso 1 1 calc R . . H11B H 0.8686 -0.2249 0.7092 0.034 Uiso 1 1 calc R . . C12 C 0.92255(17) -0.0401(2) 0.66136(16) 0.0387(4) Uani 1 1 d . . . H12A H 0.8866 0.0342 0.6103 0.058 Uiso 1 1 calc R . . H12B H 0.9832 -0.0887 0.6455 0.058 Uiso 1 1 calc R . . H12C H 0.9571 0.0035 0.7292 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01411(10) 0.01738(10) 0.01631(10) -0.00039(6) 0.00476(7) -0.00047(6) Cl1 0.02090(18) 0.02015(18) 0.02292(17) -0.00288(13) 0.00967(14) 0.00000(13) Cl2 0.01691(17) 0.0297(2) 0.02283(18) -0.00281(15) 0.00861(14) -0.00386(14) N1 0.0162(6) 0.0174(6) 0.0175(6) -0.0011(5) 0.0060(5) 0.0021(5) N2 0.0166(6) 0.0169(6) 0.0157(5) 0.0011(5) 0.0035(5) 0.0014(5) N3 0.0166(6) 0.0200(6) 0.0161(5) 0.0011(5) 0.0047(5) 0.0012(5) N4 0.0175(6) 0.0179(6) 0.0162(6) 0.0006(5) 0.0056(5) 0.0019(5) C1 0.0149(7) 0.0227(7) 0.0199(7) -0.0001(6) 0.0066(6) 0.0029(6) C2 0.0172(7) 0.0220(7) 0.0194(7) 0.0001(6) 0.0081(6) 0.0013(6) C3 0.0189(7) 0.0170(7) 0.0154(6) -0.0032(5) 0.0050(5) 0.0008(5) C4 0.0142(7) 0.0220(8) 0.0254(7) 0.0005(6) 0.0030(6) 0.0017(5) C5 0.0151(7) 0.0216(8) 0.0262(8) 0.0000(6) 0.0063(6) -0.0016(5) C6 0.0153(6) 0.0189(7) 0.0209(7) 0.0004(6) 0.0055(5) 0.0009(5) C7 0.0215(7) 0.0203(7) 0.0173(7) -0.0027(6) 0.0046(6) 0.0029(6) C8 0.0210(7) 0.0154(7) 0.0182(7) -0.0010(5) 0.0058(6) 0.0000(5) C9 0.0219(7) 0.0210(7) 0.0227(7) -0.0040(6) 0.0066(6) 0.0039(6) C10 0.0263(8) 0.0235(8) 0.0220(7) 0.0030(6) 0.0113(6) 0.0062(6) C11 0.0261(8) 0.0343(9) 0.0278(8) -0.0036(7) 0.0126(7) 0.0064(7) C12 0.0346(10) 0.0453(11) 0.0436(10) 0.0125(9) 0.0234(8) 0.0074(8) _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 2.0426(12) 4_565 ? Zn1 N1 2.0458(13) . ? Zn1 Cl2 2.2204(4) . ? Zn1 Cl1 2.2450(4) . ? N1 C5 1.342(2) . ? N1 C1 1.344(2) . ? N2 N3 1.3320(16) . ? N2 C7 1.3508(19) . ? N2 C6 1.4588(18) . ? N3 N4 1.3224(17) . ? N4 C8 1.3664(19) . ? N4 Zn1 2.0426(12) 4_666 ? C1 C2 1.384(2) . ? C2 C3 1.388(2) . ? C3 C4 1.389(2) . ? C3 C6 1.510(2) . ? C4 C5 1.383(2) . ? C7 C8 1.370(2) . ? C8 C9 1.489(2) . ? C9 C10 1.532(2) . ? C10 C11 1.519(2) . ? C11 C12 1.519(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Zn1 N1 104.67(5) 4_565 . ? N4 Zn1 Cl2 114.47(4) 4_565 . ? N1 Zn1 Cl2 109.49(4) . . ? N4 Zn1 Cl1 107.26(4) 4_565 . ? N1 Zn1 Cl1 103.72(4) . . ? Cl2 Zn1 Cl1 116.099(15) . . ? C5 N1 C1 117.99(13) . . ? C5 N1 Zn1 120.74(11) . . ? C1 N1 Zn1 121.10(10) . . ? N3 N2 C7 111.70(12) . . ? N3 N2 C6 119.59(12) . . ? C7 N2 C6 128.65(12) . . ? N4 N3 N2 105.89(11) . . ? N3 N4 C8 110.44(12) . . ? N3 N4 Zn1 114.73(9) . 4_666 ? C8 N4 Zn1 134.19(10) . 4_666 ? N1 C1 C2 122.73(14) . . ? C1 C2 C3 119.25(14) . . ? C2 C3 C4 117.95(14) . . ? C2 C3 C6 119.06(13) . . ? C4 C3 C6 122.98(13) . . ? C5 C4 C3 119.59(14) . . ? N1 C5 C4 122.46(14) . . ? N2 C6 C3 112.61(12) . . ? N2 C7 C8 105.40(13) . . ? N4 C8 C7 106.56(13) . . ? N4 C8 C9 122.35(13) . . ? C7 C8 C9 130.88(14) . . ? C8 C9 C10 111.13(13) . . ? C11 C10 C9 112.44(14) . . ? C10 C11 C12 113.33(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.444 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.069 #===end data_9429a _database_code_depnum_ccdc_archive 'CCDC 751945' #TrackingRef '- CEC-CIF-29Jun2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 Cl2 N4 Zn' _chemical_formula_weight 366.58 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' 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 16.6738(8) _cell_length_b 8.9880(4) _cell_length_c 11.4645(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.8240(10) _cell_angle_gamma 90.00 _cell_volume 1644.58(14) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6272 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.43 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.813 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4300 _exptl_absorpt_correction_T_max 0.8395 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11199 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3759 _reflns_number_gt 3432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0644P)^2^+0.1363P] 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 3759 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.226 _refine_ls_restrained_S_all 1.226 _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 0.302515(14) 0.08639(2) 0.718327(19) 0.02767(11) Uani 1 1 d . . . Cl1 Cl 0.32443(3) 0.01506(6) 0.91112(4) 0.03717(14) Uani 1 1 d . . . Cl2 Cl 0.23568(4) -0.07158(6) 0.57465(5) 0.04004(15) Uani 1 1 d . . . N1 N 0.25820(10) 0.29810(18) 0.70185(15) 0.0291(3) Uani 1 1 d . . . N2 N 0.30301(11) 0.38476(19) 0.79036(16) 0.0319(4) Uani 1 1 d . . . N3 N 0.27929(10) 0.52298(17) 0.75567(16) 0.0296(3) Uani 1 1 d . . . N4 N 0.57909(11) 0.62044(18) 0.79985(15) 0.0304(3) Uani 1 1 d . . . C1 C 0.20746(12) 0.3812(2) 0.61071(19) 0.0310(4) Uani 1 1 d . . . C2 C 0.22142(13) 0.5267(2) 0.6462(2) 0.0332(4) Uani 1 1 d . . . H2 H 0.1959 0.6114 0.6031 0.040 Uiso 1 1 calc R . . C3 C 0.32727(14) 0.6453(2) 0.8269(2) 0.0354(4) Uani 1 1 d . . . H3A H 0.3281 0.6355 0.9124 0.042 Uiso 1 1 calc R . . H3B H 0.3008 0.7404 0.7961 0.042 Uiso 1 1 calc R . . C4 C 0.56396(15) 0.6613(3) 0.9039(2) 0.0442(5) Uani 1 1 d . . . H4 H 0.6097 0.6827 0.9721 0.053 Uiso 1 1 calc R . . C5 C 0.48463(15) 0.6732(3) 0.9151(2) 0.0453(6) Uani 1 1 d . . . H5 H 0.4771 0.7027 0.9899 0.054 Uiso 1 1 calc R . . C6 C 0.41571(13) 0.6423(2) 0.81771(19) 0.0314(4) Uani 1 1 d . . . C7 C 0.43131(16) 0.6042(4) 0.7100(2) 0.0534(7) Uani 1 1 d . . . H7 H 0.3865 0.5857 0.6400 0.064 Uiso 1 1 calc R . . C8 C 0.51239(16) 0.5930(3) 0.7048(2) 0.0500(7) Uani 1 1 d . . . H8 H 0.5214 0.5646 0.6307 0.060 Uiso 1 1 calc R . . C9 C 0.14986(13) 0.3137(3) 0.49790(19) 0.0374(5) Uani 1 1 d . . . H9A H 0.1796 0.2348 0.4684 0.045 Uiso 1 1 calc R . . H9B H 0.1337 0.3900 0.4343 0.045 Uiso 1 1 calc R . . C10 C 0.07135(17) 0.2490(4) 0.5203(2) 0.0538(6) Uani 1 1 d . . . H10A H 0.0413 0.3286 0.5484 0.065 Uiso 1 1 calc R . . H10B H 0.0879 0.1747 0.5854 0.065 Uiso 1 1 calc R . . C11 C 0.01183(18) 0.1761(3) 0.4071(3) 0.0579(7) Uani 1 1 d . . . H11A H 0.0428 0.0994 0.3774 0.069 Uiso 1 1 calc R . . H11B H -0.0333 0.1265 0.4311 0.069 Uiso 1 1 calc R . . C12 C -0.02659(17) 0.2809(3) 0.3045(3) 0.0518(6) Uani 1 1 d . . . H12A H 0.0177 0.3223 0.2737 0.062 Uiso 1 1 calc R . . H12B H -0.0528 0.3636 0.3356 0.062 Uiso 1 1 calc R . . C13 C -0.09207(18) 0.2063(4) 0.2000(3) 0.0652(8) Uani 1 1 d . . . H13A H -0.0655 0.1297 0.1644 0.098 Uiso 1 1 calc R . . H13B H -0.1174 0.2799 0.1385 0.098 Uiso 1 1 calc R . . H13C H -0.1350 0.1617 0.2305 0.098 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.03146(16) 0.02354(15) 0.02614(16) -0.00083(7) 0.00535(11) 0.00071(8) Cl1 0.0501(3) 0.0349(3) 0.0266(3) 0.00173(18) 0.0113(2) 0.0010(2) Cl2 0.0487(3) 0.0345(3) 0.0343(3) -0.00914(19) 0.0079(2) -0.0084(2) N1 0.0305(8) 0.0258(8) 0.0289(8) -0.0015(6) 0.0051(6) 0.0005(6) N2 0.0369(9) 0.0253(7) 0.0304(9) -0.0041(6) 0.0047(7) -0.0003(7) N3 0.0290(8) 0.0238(8) 0.0373(9) -0.0021(7) 0.0116(7) 0.0001(6) N4 0.0326(8) 0.0295(8) 0.0273(8) -0.0011(6) 0.0059(7) -0.0028(7) C1 0.0269(9) 0.0309(9) 0.0343(10) 0.0041(8) 0.0072(8) 0.0015(8) C2 0.0285(9) 0.0286(10) 0.0424(11) 0.0053(8) 0.0097(8) 0.0026(8) C3 0.0398(11) 0.0282(9) 0.0415(11) -0.0088(8) 0.0169(9) -0.0044(8) C4 0.0407(12) 0.0555(14) 0.0330(11) -0.0171(10) 0.0051(9) -0.0063(10) C5 0.0441(12) 0.0584(14) 0.0346(11) -0.0229(10) 0.0134(10) -0.0091(11) C6 0.0358(10) 0.0255(9) 0.0336(10) -0.0027(8) 0.0113(8) -0.0024(8) C7 0.0325(12) 0.099(2) 0.0262(11) -0.0126(12) 0.0046(9) -0.0098(12) C8 0.0358(12) 0.087(2) 0.0264(11) -0.0114(11) 0.0086(9) -0.0057(12) C9 0.0340(10) 0.0403(11) 0.0336(10) 0.0050(9) 0.0030(8) -0.0016(9) C10 0.0424(13) 0.0672(16) 0.0478(14) 0.0054(12) 0.0066(11) -0.0164(12) C11 0.0466(14) 0.0580(15) 0.0583(16) 0.0066(13) -0.0019(12) -0.0190(12) C12 0.0428(13) 0.0522(14) 0.0527(14) 0.0008(12) 0.0017(11) -0.0025(11) C13 0.0444(15) 0.082(2) 0.0562(16) 0.0021(15) -0.0066(12) -0.0083(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 N1 2.0302(16) . ? Zn1 N4 2.0669(18) 2_646 ? Zn1 Cl2 2.2155(5) . ? Zn1 Cl1 2.2276(5) . ? N1 N2 1.325(2) . ? N1 C1 1.361(3) . ? N2 N3 1.329(2) . ? N3 C2 1.344(3) . ? N3 C3 1.462(3) . ? N4 C8 1.336(3) . ? N4 C4 1.340(3) . ? N4 Zn1 2.0669(18) 2_656 ? C1 C2 1.370(3) . ? C1 C9 1.498(3) . ? C3 C6 1.509(3) . ? C4 C5 1.370(3) . ? C5 C6 1.379(3) . ? C6 C7 1.377(3) . ? C7 C8 1.374(3) . ? C9 C10 1.520(3) . ? C10 C11 1.534(4) . ? C11 C12 1.498(4) . ? C12 C13 1.524(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N4 100.62(7) . 2_646 ? N1 Zn1 Cl2 116.12(5) . . ? N4 Zn1 Cl2 108.03(5) 2_646 . ? N1 Zn1 Cl1 108.23(5) . . ? N4 Zn1 Cl1 104.80(5) 2_646 . ? Cl2 Zn1 Cl1 117.13(2) . . ? N2 N1 C1 110.66(16) . . ? N2 N1 Zn1 111.73(12) . . ? C1 N1 Zn1 135.57(14) . . ? N1 N2 N3 105.50(16) . . ? N2 N3 C2 111.94(16) . . ? N2 N3 C3 117.91(17) . . ? C2 N3 C3 129.20(17) . . ? C8 N4 C4 116.7(2) . . ? C8 N4 Zn1 118.98(15) . 2_656 ? C4 N4 Zn1 124.17(14) . 2_656 ? N1 C1 C2 106.34(18) . . ? N1 C1 C9 122.78(18) . . ? C2 C1 C9 130.88(19) . . ? N3 C2 C1 105.55(17) . . ? N3 C3 C6 109.62(16) . . ? N4 C4 C5 122.7(2) . . ? C4 C5 C6 120.7(2) . . ? C7 C6 C5 116.5(2) . . ? C7 C6 C3 120.61(19) . . ? C5 C6 C3 122.84(19) . . ? C8 C7 C6 120.1(2) . . ? N4 C8 C7 123.3(2) . . ? C1 C9 C10 112.18(19) . . ? C9 C10 C11 113.5(2) . . ? C12 C11 C10 114.9(2) . . ? C11 C12 C13 112.8(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.600 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.128 #===end data_9493 _database_code_depnum_ccdc_archive 'CCDC 751946' #TrackingRef '- CEC-CIF-29Jun2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 Cl2 N4 Zn' _chemical_formula_weight 380.61 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' 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 11.9395(6) _cell_length_b 8.8292(5) _cell_length_c 15.6367(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.7300(10) _cell_angle_gamma 90.00 _cell_volume 1637.00(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3686 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.29 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 1.825 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7117 _exptl_absorpt_correction_T_max 0.7842 _exptl_absorpt_process_details 'Sadabs,(Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11283 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3750 _reflns_number_gt 3255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0490P)^2^+0.2998P] 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 3750 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.283335(19) 0.55820(3) 0.129753(15) 0.01572(9) Uani 1 1 d . . . Cl1 Cl 0.15032(5) 0.66524(7) 0.19696(4) 0.02363(14) Uani 1 1 d . . . Cl2 Cl 0.45157(4) 0.66734(7) 0.14064(4) 0.02401(14) Uani 1 1 d . . . N1 N 0.28388(14) 0.3302(2) 0.15815(11) 0.0167(4) Uani 1 1 d . . . N2 N 0.19076(15) 0.2798(2) 0.18688(11) 0.0173(4) Uani 1 1 d . . . N3 N 0.20167(15) 0.1296(2) 0.19182(11) 0.0170(4) Uani 1 1 d . . . N4 N 0.22893(15) -0.0470(2) 0.50022(11) 0.0157(4) Uani 1 1 d . . . C1 C 0.11927(18) 0.0426(3) 0.23338(14) 0.0185(5) Uani 1 1 d . . . H1A H 0.1037 -0.0539 0.2020 0.022 Uiso 1 1 calc R . . H1B H 0.0478 0.1003 0.2303 0.022 Uiso 1 1 calc R . . C2 C 0.12473(18) -0.0845(2) 0.46438(14) 0.0176(4) Uani 1 1 d . . . H2 H 0.0744 -0.1297 0.4996 0.021 Uiso 1 1 calc R . . C3 C 0.08776(18) -0.0598(2) 0.37824(15) 0.0184(4) Uani 1 1 d . . . H3 H 0.0140 -0.0893 0.3548 0.022 Uiso 1 1 calc R . . C4 C 0.16052(18) 0.0092(2) 0.32634(14) 0.0164(4) Uani 1 1 d . . . C5 C 0.26855(19) 0.0443(3) 0.36309(14) 0.0183(4) Uani 1 1 d . . . H5 H 0.3209 0.0895 0.3295 0.022 Uiso 1 1 calc R . . C6 C 0.29934(18) 0.0131(3) 0.44892(14) 0.0192(5) Uani 1 1 d . . . H6 H 0.3743 0.0354 0.4729 0.023 Uiso 1 1 calc R . . C7 C 0.30102(18) 0.0829(3) 0.16683(14) 0.0187(5) Uani 1 1 d . . . H7 H 0.3280 -0.0181 0.1646 0.022 Uiso 1 1 calc R . . C8 C 0.35392(18) 0.2121(3) 0.14558(13) 0.0177(4) Uani 1 1 d . . . C9 C 0.46860(18) 0.2331(3) 0.11710(15) 0.0215(5) Uani 1 1 d . . . H9A H 0.5113 0.3075 0.1555 0.026 Uiso 1 1 calc R . . H9B H 0.4600 0.2753 0.0580 0.026 Uiso 1 1 calc R . . C10 C 0.53575(18) 0.0864(3) 0.11803(15) 0.0194(5) Uani 1 1 d . . . H10A H 0.4937 0.0115 0.0796 0.023 Uiso 1 1 calc R . . H10B H 0.5454 0.0441 0.1771 0.023 Uiso 1 1 calc R . . C11 C 0.65124(18) 0.1135(3) 0.08834(14) 0.0191(4) Uani 1 1 d . . . H11A H 0.6935 0.1866 0.1279 0.023 Uiso 1 1 calc R . . H11B H 0.6410 0.1596 0.0302 0.023 Uiso 1 1 calc R . . C12 C 0.72079(18) -0.0313(3) 0.08539(15) 0.0192(5) Uani 1 1 d . . . H12A H 0.7323 -0.0767 0.1437 0.023 Uiso 1 1 calc R . . H12B H 0.6783 -0.1051 0.0464 0.023 Uiso 1 1 calc R . . C13 C 0.83504(19) -0.0022(3) 0.05437(16) 0.0225(5) Uani 1 1 d . . . H13A H 0.8790 0.0673 0.0951 0.027 Uiso 1 1 calc R . . H13B H 0.8235 0.0484 -0.0025 0.027 Uiso 1 1 calc R . . C14 C 0.9026(2) -0.1473(3) 0.04664(19) 0.0309(6) Uani 1 1 d . . . H14A H 0.9181 -0.1949 0.1034 0.046 Uiso 1 1 calc R . . H14B H 0.9740 -0.1230 0.0246 0.046 Uiso 1 1 calc R . . H14C H 0.8591 -0.2173 0.0069 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01431(14) 0.01513(15) 0.01818(14) -0.00006(10) 0.00390(9) 0.00042(9) Cl1 0.0209(3) 0.0218(3) 0.0294(3) -0.0055(2) 0.0079(2) 0.0042(2) Cl2 0.0158(3) 0.0272(3) 0.0289(3) 0.0029(2) 0.0020(2) -0.0042(2) N1 0.0162(9) 0.0168(9) 0.0178(9) 0.0001(7) 0.0048(7) 0.0000(7) N2 0.0165(9) 0.0169(9) 0.0189(9) 0.0012(7) 0.0044(7) 0.0014(7) N3 0.0170(9) 0.0164(10) 0.0183(9) 0.0017(7) 0.0051(7) 0.0010(7) N4 0.0151(9) 0.0142(9) 0.0181(9) -0.0024(7) 0.0036(7) 0.0004(7) C1 0.0166(10) 0.0171(11) 0.0222(11) -0.0013(9) 0.0037(8) -0.0017(8) C2 0.0152(10) 0.0156(11) 0.0230(11) 0.0011(9) 0.0059(8) -0.0007(8) C3 0.0139(10) 0.0161(11) 0.0248(11) -0.0018(9) 0.0013(8) -0.0004(8) C4 0.0173(10) 0.0124(10) 0.0194(10) -0.0019(8) 0.0019(8) 0.0009(8) C5 0.0167(11) 0.0181(11) 0.0213(11) -0.0002(9) 0.0072(8) -0.0021(9) C6 0.0146(10) 0.0206(11) 0.0224(11) -0.0017(9) 0.0020(8) -0.0019(9) C7 0.0193(11) 0.0162(11) 0.0210(11) -0.0003(9) 0.0036(8) 0.0051(9) C8 0.0177(10) 0.0180(11) 0.0179(10) 0.0013(9) 0.0043(8) 0.0045(9) C9 0.0182(11) 0.0192(12) 0.0285(12) 0.0037(10) 0.0086(9) 0.0021(9) C10 0.0171(10) 0.0189(12) 0.0230(11) 0.0005(9) 0.0056(8) 0.0024(9) C11 0.0187(11) 0.0168(11) 0.0221(11) 0.0010(9) 0.0043(8) 0.0023(9) C12 0.0174(11) 0.0183(12) 0.0228(11) 0.0009(9) 0.0062(8) 0.0018(9) C13 0.0180(11) 0.0197(12) 0.0306(12) 0.0014(10) 0.0063(9) 0.0028(9) C14 0.0203(12) 0.0213(13) 0.0538(17) 0.0014(12) 0.0149(11) 0.0044(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N4 2.0558(18) 4_565 ? Zn1 N1 2.0614(19) . ? Zn1 Cl1 2.2161(6) . ? Zn1 Cl2 2.2163(6) . ? N1 N2 1.324(2) . ? N1 C8 1.365(3) . ? N2 N3 1.334(3) . ? N3 C7 1.356(3) . ? N3 C1 1.459(3) . ? N4 C6 1.338(3) . ? N4 C2 1.345(3) . ? N4 Zn1 2.0557(18) 4_566 ? C1 C4 1.508(3) . ? C2 C3 1.385(3) . ? C3 C4 1.396(3) . ? C4 C5 1.384(3) . ? C5 C6 1.377(3) . ? C7 C8 1.364(3) . ? C8 C9 1.500(3) . ? C9 C10 1.523(3) . ? C10 C11 1.525(3) . ? C11 C12 1.529(3) . ? C12 C13 1.522(3) . ? C13 C14 1.527(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Zn1 N1 99.09(7) 4_565 . ? N4 Zn1 Cl1 109.06(5) 4_565 . ? N1 Zn1 Cl1 107.38(5) . . ? N4 Zn1 Cl2 105.99(5) 4_565 . ? N1 Zn1 Cl2 115.35(5) . . ? Cl1 Zn1 Cl2 118.13(2) . . ? N2 N1 C8 110.21(18) . . ? N2 N1 Zn1 114.80(13) . . ? C8 N1 Zn1 134.53(15) . . ? N1 N2 N3 105.86(17) . . ? N2 N3 C7 111.62(18) . . ? N2 N3 C1 118.85(18) . . ? C7 N3 C1 128.79(19) . . ? C6 N4 C2 117.61(19) . . ? C6 N4 Zn1 117.49(14) . 4_566 ? C2 N4 Zn1 124.68(15) . 4_566 ? N3 C1 C4 111.79(18) . . ? N4 C2 C3 122.7(2) . . ? C2 C3 C4 119.0(2) . . ? C5 C4 C3 118.0(2) . . ? C5 C4 C1 122.6(2) . . ? C3 C4 C1 119.37(19) . . ? C6 C5 C4 119.3(2) . . ? N4 C6 C5 123.3(2) . . ? N3 C7 C8 105.16(19) . . ? C7 C8 N1 107.14(18) . . ? C7 C8 C9 129.8(2) . . ? N1 C8 C9 123.0(2) . . ? C8 C9 C10 112.95(19) . . ? C9 C10 C11 110.94(19) . . ? C10 C11 C12 113.05(19) . . ? C13 C12 C11 112.23(19) . . ? C12 C13 C14 112.6(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.763 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.090 #===end data_9513 _database_code_depnum_ccdc_archive 'CCDC 761504' #TrackingRef '- CEC-CIF-29Jun2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H40 Cl2 Co N8 O12' _chemical_formula_weight 762.47 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1059(7) _cell_length_b 9.7570(7) _cell_length_c 19.2007(14) _cell_angle_alpha 90.00 _cell_angle_beta 101.220(2) _cell_angle_gamma 90.00 _cell_volume 1673.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4824 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.51 _exptl_crystal_description BLOCK _exptl_crystal_colour PINK _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 794 _exptl_absorpt_coefficient_mu 0.743 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6642 _exptl_absorpt_correction_T_max 0.9294 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11641 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3844 _reflns_number_gt 3427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0507P)^2^+0.7089P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3844 _refine_ls_number_parameters 231 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0921 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 Co1 Co 0.0000 0.5000 0.0000 0.01221(10) Uani 1 2 d S . . O1 O 0.04303(14) 0.70478(13) 0.03178(7) 0.0173(3) Uani 1 1 d D . . H11 H -0.023(3) 0.745(3) 0.0467(15) 0.049(8) Uiso 1 1 d D . . H12 H 0.110(3) 0.759(2) 0.0265(14) 0.044(8) Uiso 1 1 d D . . N1 N -0.07613(15) 0.45957(15) 0.09730(8) 0.0144(3) Uani 1 1 d . . . N2 N -0.19284(16) 0.37622(15) 0.09040(7) 0.0154(3) Uani 1 1 d . . . N3 N -0.22425(15) 0.36389(14) 0.15507(7) 0.0141(3) Uani 1 1 d . . . N4 N -0.77887(15) 0.43096(14) 0.05311(7) 0.0142(3) Uani 1 1 d . . . C1 C -0.76127(19) 0.30381(17) 0.08085(9) 0.0154(3) Uani 1 1 d . . . H1 H -0.8469 0.2464 0.0762 0.018 Uiso 1 1 calc R . . C2 C -0.62546(19) 0.25250(17) 0.11563(9) 0.0148(3) Uani 1 1 d . . . H2 H -0.6180 0.1609 0.1327 0.018 Uiso 1 1 calc R . . C3 C -0.49942(18) 0.33653(17) 0.12548(9) 0.0135(3) Uani 1 1 d . . . C4 C -0.51685(19) 0.46847(17) 0.09846(9) 0.0154(3) Uani 1 1 d . . . H4 H -0.4340 0.5295 0.1046 0.018 Uiso 1 1 calc R . . C5 C -0.65637(19) 0.51043(17) 0.06240(10) 0.0159(3) Uani 1 1 d . . . H5 H -0.6658 0.6004 0.0432 0.019 Uiso 1 1 calc R . . C6 C -0.35168(19) 0.28021(18) 0.16429(9) 0.0164(3) Uani 1 1 d . . . H6A H -0.3538 0.2739 0.2155 0.020 Uiso 1 1 calc R . . H6B H -0.3385 0.1864 0.1469 0.020 Uiso 1 1 calc R . . C7 C -0.12933(19) 0.43710(17) 0.20368(9) 0.0162(3) Uani 1 1 d . . . H7 H -0.1289 0.4444 0.2531 0.019 Uiso 1 1 calc R . . C8 C -0.03297(19) 0.49912(16) 0.16630(9) 0.0152(3) Uani 1 1 d . . . C9 C 0.09747(19) 0.59118(18) 0.19337(9) 0.0179(3) Uani 1 1 d . . . H9A H 0.0630 0.6682 0.2197 0.021 Uiso 1 1 calc R . . H9B H 0.1344 0.6302 0.1524 0.021 Uiso 1 1 calc R . . C10 C 0.2265(2) 0.51863(18) 0.24187(10) 0.0184(4) Uani 1 1 d . . . H10A H 0.2572 0.4382 0.2167 0.022 Uiso 1 1 calc R . . H10B H 0.1918 0.4850 0.2845 0.022 Uiso 1 1 calc R . . C11 C 0.3615(2) 0.61217(19) 0.26490(10) 0.0216(4) Uani 1 1 d . . . H11A H 0.4012 0.6403 0.2226 0.026 Uiso 1 1 calc R . . H11B H 0.3295 0.6959 0.2870 0.026 Uiso 1 1 calc R . . C12 C 0.4850(3) 0.5416(2) 0.31756(15) 0.0427(6) Uani 1 1 d . . . H12A H 0.4449 0.5099 0.3586 0.064 Uiso 1 1 calc R . . H12B H 0.5669 0.6064 0.3334 0.064 Uiso 1 1 calc R . . H12C H 0.5228 0.4630 0.2946 0.064 Uiso 1 1 calc R . . O1W O 0.25592(17) 0.89738(15) 0.03613(9) 0.0315(3) Uani 1 1 d D . . H1WA H 0.340(2) 0.866(3) 0.0366(16) 0.056(9) Uiso 1 1 d D . . H1WB H 0.240(4) 0.959(3) 0.0059(14) 0.055(9) Uiso 1 1 d D . . Cl1 Cl -0.32661(4) 0.83612(4) 0.09612(2) 0.01670(11) Uani 1 1 d . . . O2 O -0.27286(17) 0.74680(15) 0.15465(7) 0.0304(3) Uani 1 1 d . . . O3 O -0.44574(15) 0.77102(14) 0.04705(7) 0.0240(3) Uani 1 1 d . . . O4 O -0.38102(16) 0.96149(14) 0.12125(8) 0.0267(3) Uani 1 1 d . . . O5 O -0.20486(15) 0.86789(14) 0.05976(7) 0.0248(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.00820(16) 0.01432(17) 0.01408(17) 0.00039(11) 0.00208(11) -0.00105(11) O1 0.0124(6) 0.0173(6) 0.0225(6) -0.0010(5) 0.0042(5) -0.0017(5) N1 0.0093(6) 0.0165(7) 0.0172(7) 0.0005(5) 0.0018(5) -0.0009(5) N2 0.0116(7) 0.0187(7) 0.0162(7) 0.0010(6) 0.0034(5) 0.0001(5) N3 0.0106(6) 0.0155(7) 0.0160(7) 0.0024(5) 0.0025(5) 0.0009(5) N4 0.0116(6) 0.0164(7) 0.0150(7) 0.0003(5) 0.0034(5) 0.0000(5) C1 0.0136(8) 0.0170(8) 0.0157(8) 0.0001(6) 0.0035(6) -0.0034(6) C2 0.0160(8) 0.0143(8) 0.0142(8) 0.0014(6) 0.0030(6) -0.0013(6) C3 0.0110(7) 0.0171(8) 0.0131(7) -0.0010(6) 0.0038(6) 0.0005(6) C4 0.0113(8) 0.0151(8) 0.0197(8) -0.0004(6) 0.0028(6) -0.0020(6) C5 0.0121(8) 0.0143(8) 0.0209(8) 0.0025(6) 0.0025(6) 0.0012(6) C6 0.0109(7) 0.0165(8) 0.0217(8) 0.0054(7) 0.0027(6) -0.0014(6) C7 0.0141(8) 0.0171(8) 0.0172(8) 0.0005(6) 0.0022(6) -0.0002(6) C8 0.0118(8) 0.0161(8) 0.0170(8) 0.0012(6) 0.0009(6) 0.0019(6) C9 0.0155(8) 0.0183(8) 0.0192(8) -0.0017(7) 0.0014(6) -0.0040(7) C10 0.0153(8) 0.0168(8) 0.0217(9) -0.0038(7) 0.0003(7) -0.0005(6) C11 0.0151(8) 0.0214(9) 0.0274(9) -0.0055(7) 0.0018(7) -0.0018(7) C12 0.0225(11) 0.0308(12) 0.0655(17) -0.0070(11) -0.0144(11) 0.0009(9) O1W 0.0195(7) 0.0248(8) 0.0504(10) 0.0071(7) 0.0079(7) -0.0034(6) Cl1 0.0167(2) 0.0141(2) 0.0189(2) -0.00164(15) 0.00250(15) -0.00017(14) O2 0.0335(8) 0.0266(7) 0.0276(7) 0.0070(6) -0.0026(6) 0.0018(6) O3 0.0206(7) 0.0240(7) 0.0260(7) -0.0033(5) 0.0013(5) -0.0062(5) O4 0.0295(8) 0.0178(6) 0.0348(8) -0.0055(6) 0.0114(6) 0.0021(5) O5 0.0175(6) 0.0267(7) 0.0316(7) -0.0034(6) 0.0083(5) -0.0022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.1036(13) . ? Co1 O1 2.1037(13) 3_565 ? Co1 N1 2.1518(14) . ? Co1 N1 2.1518(14) 3_565 ? Co1 N4 2.1793(14) 1_655 ? Co1 N4 2.1794(14) 3_465 ? N1 N2 1.324(2) . ? N1 C8 1.362(2) . ? N2 N3 1.333(2) . ? N3 C7 1.347(2) . ? N3 C6 1.457(2) . ? N4 C5 1.342(2) . ? N4 C1 1.347(2) . ? N4 Co1 2.1793(14) 1_455 ? C1 C2 1.380(2) . ? C2 C3 1.393(2) . ? C3 C4 1.385(2) . ? C3 C6 1.509(2) . ? C4 C5 1.385(2) . ? C7 C8 1.377(2) . ? C8 C9 1.499(2) . ? C9 C10 1.524(2) . ? C10 C11 1.526(2) . ? C11 C12 1.523(3) . ? Cl1 O2 1.4310(14) . ? Cl1 O4 1.4379(13) . ? Cl1 O3 1.4388(13) . ? Cl1 O5 1.4539(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 180.0 . 3_565 ? O1 Co1 N1 89.75(5) . . ? O1 Co1 N1 90.25(5) 3_565 . ? O1 Co1 N1 90.25(5) . 3_565 ? O1 Co1 N1 89.75(5) 3_565 3_565 ? N1 Co1 N1 180.0 . 3_565 ? O1 Co1 N4 93.15(5) . 1_655 ? O1 Co1 N4 86.86(5) 3_565 1_655 ? N1 Co1 N4 87.79(5) . 1_655 ? N1 Co1 N4 92.21(5) 3_565 1_655 ? O1 Co1 N4 86.85(5) . 3_465 ? O1 Co1 N4 93.15(5) 3_565 3_465 ? N1 Co1 N4 92.21(5) . 3_465 ? N1 Co1 N4 87.79(5) 3_565 3_465 ? N4 Co1 N4 180.0 1_655 3_465 ? N2 N1 C8 110.20(14) . . ? N2 N1 Co1 114.43(11) . . ? C8 N1 Co1 135.37(12) . . ? N1 N2 N3 106.01(13) . . ? N2 N3 C7 111.87(14) . . ? N2 N3 C6 118.94(14) . . ? C7 N3 C6 129.17(14) . . ? C5 N4 C1 116.60(14) . . ? C5 N4 Co1 123.52(11) . 1_455 ? C1 N4 Co1 119.84(11) . 1_455 ? N4 C1 C2 123.49(15) . . ? C1 C2 C3 119.29(15) . . ? C4 C3 C2 117.69(15) . . ? C4 C3 C6 123.33(15) . . ? C2 C3 C6 118.98(15) . . ? C5 C4 C3 119.27(15) . . ? N4 C5 C4 123.62(15) . . ? N3 C6 C3 112.98(13) . . ? N3 C7 C8 105.06(15) . . ? N1 C8 C7 106.85(15) . . ? N1 C8 C9 124.47(15) . . ? C7 C8 C9 128.67(16) . . ? C8 C9 C10 113.47(14) . . ? C9 C10 C11 112.40(14) . . ? C12 C11 C10 111.78(16) . . ? O2 Cl1 O4 110.01(9) . . ? O2 Cl1 O3 110.15(8) . . ? O4 Cl1 O3 109.28(9) . . ? O2 Cl1 O5 109.31(9) . . ? O4 Cl1 O5 108.93(8) . . ? O3 Cl1 O5 109.14(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H11 O5 0.815(17) 2.099(18) 2.8963(18) 166(3) . O1 H12 O1W 0.824(17) 1.882(18) 2.6895(19) 166(3) . O1W H1WA O3 0.828(18) 2.129(18) 2.953(2) 174(3) 1_655 O1W H1WB O5 0.830(18) 2.093(18) 2.919(2) 173(3) 3_575 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.525 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.073 #===end data_a080a _database_code_depnum_ccdc_archive 'CCDC 767450' #TrackingRef '- CEC-CIF-29Jun2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H43 Cl2 Cu N8 O11' _chemical_formula_weight 790.13 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.9695(5) _cell_length_b 15.7723(9) _cell_length_c 12.5159(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.5880(10) _cell_angle_gamma 90.00 _cell_volume 1750.77(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6070 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.46 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not MeaSURED' _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.844 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6493 _exptl_absorpt_correction_T_max 0.9204 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12458 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6455 _reflns_number_gt 6061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0641P)^2^+0.9849P] 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 0.023(13) _refine_ls_number_reflns 6455 _refine_ls_number_parameters 453 _refine_ls_number_restraints 41 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.126 _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 Cl2 Cl 0.63870(12) 0.03426(7) 0.23201(8) 0.0274(2) Uani 1 1 d D . . O5 O 0.6006(6) 0.1151(3) 0.2582(4) 0.0617(9) Uani 1 1 d D A . O6 O 0.5791(9) -0.0308(4) 0.2918(6) 0.0617(9) Uani 0.723(6) 1 d PD A 1 O7 O 0.5636(8) 0.0256(4) 0.1181(5) 0.0617(9) Uani 0.723(6) 1 d PD A 1 O8 O 0.7904(7) 0.0236(4) 0.2337(5) 0.0617(9) Uani 0.723(6) 1 d PD A 1 O6A O 0.5439(12) -0.0313(7) 0.2663(9) 0.023(3) Uiso 0.277(6) 1 d PD A 2 O7A O 0.6810(15) 0.0148(8) 0.1350(8) 0.045(4) Uiso 0.277(6) 1 d PD A 2 O8A O 0.7882(12) 0.0195(8) 0.3156(9) 0.044(4) Uiso 0.277(6) 1 d PD A 2 Cu1 Cu 0.97713(4) 0.28499(3) 0.76511(3) 0.01458(11) Uani 1 1 d . . . N1 N 1.1440(4) 0.2391(2) 0.6919(3) 0.0180(7) Uani 1 1 d . . . N2 N 1.6392(4) 0.1821(2) 0.5577(2) 0.0174(7) Uani 1 1 d . . . N3 N 1.7211(3) 0.1968(2) 0.6540(3) 0.0179(7) Uani 1 1 d . . . N4 N 1.8290(3) 0.2497(2) 0.6354(3) 0.0174(7) Uani 1 1 d . . . N5 N 0.8143(3) 0.2780(2) 0.8598(2) 0.0160(6) Uani 1 1 d . . . N6 N 0.3226(3) 0.2815(3) 1.0118(2) 0.0176(6) Uani 1 1 d . . . N7 N 0.2382(3) 0.2535(2) 0.9220(2) 0.0177(7) Uani 1 1 d . . . N8 N 0.1273(3) 0.3094(2) 0.8991(2) 0.0171(7) Uani 1 1 d . . . C1 C 1.2678(4) 0.2847(3) 0.6829(3) 0.0172(7) Uani 1 1 d . . . H1 H 1.2737 0.3414 0.7086 0.021 Uiso 1 1 calc R . . C2 C 1.3864(4) 0.2523(3) 0.6379(3) 0.0174(8) Uani 1 1 d . . . H2 H 1.4722 0.2864 0.6327 0.021 Uiso 1 1 calc R . . C3 C 1.3802(4) 0.1702(3) 0.6006(3) 0.0182(8) Uani 1 1 d . . . C4 C 1.2520(4) 0.1227(3) 0.6082(3) 0.0191(8) Uani 1 1 d . . . H4 H 1.2437 0.0661 0.5821 0.023 Uiso 1 1 calc R . . C5 C 1.1354(4) 0.1594(3) 0.6547(3) 0.0190(8) Uani 1 1 d . . . H5 H 1.0476 0.1269 0.6601 0.023 Uiso 1 1 calc R . . C6 C 1.5067(4) 0.1276(3) 0.5520(3) 0.0233(9) Uani 1 1 d . . . H6A H 1.5351 0.0742 0.5912 0.028 Uiso 1 1 calc R . . H6B H 1.4704 0.1133 0.4755 0.028 Uiso 1 1 calc R . . C7 C 1.6931(4) 0.2242(3) 0.4779(3) 0.0204(8) Uani 1 1 d . . . H7 H 1.6535 0.2237 0.4032 0.025 Uiso 1 1 calc R . . C8 C 1.8176(4) 0.2682(3) 0.5270(3) 0.0172(8) Uani 1 1 d . . . C9 C 1.9169(5) 0.3274(3) 0.4785(3) 0.0228(8) Uani 1 1 d . . . H9A H 2.0182 0.3268 0.5225 0.027 Uiso 1 1 calc R . . H9B H 1.8761 0.3856 0.4813 0.027 Uiso 1 1 calc R . . C10 C 1.9327(5) 0.3061(3) 0.3604(3) 0.0239(9) Uani 1 1 d . . . H10A H 1.8310 0.2964 0.3193 0.029 Uiso 1 1 calc R . . H10B H 1.9770 0.3555 0.3278 0.029 Uiso 1 1 calc R . . C11 C 2.0302(5) 0.2283(3) 0.3484(3) 0.0237(9) Uani 1 1 d . . . H11A H 2.1295 0.2355 0.3940 0.028 Uiso 1 1 calc R . . H11B H 1.9813 0.1775 0.3741 0.028 Uiso 1 1 calc R . . C12 C 2.0531(6) 0.2150(4) 0.2316(3) 0.0341(11) Uani 1 1 d . . . H12A H 2.0933 0.2680 0.2044 0.041 Uiso 1 1 calc R . . H12B H 1.9540 0.2036 0.1875 0.041 Uiso 1 1 calc R . . C13 C 2.1598(8) 0.1425(4) 0.2162(5) 0.0483(15) Uani 1 1 d . . . H13A H 2.2622 0.1572 0.2502 0.072 Uiso 1 1 calc R . . H13B H 2.1592 0.1327 0.1388 0.072 Uiso 1 1 calc R . . H13C H 2.1269 0.0910 0.2497 0.072 Uiso 1 1 calc R . . C14 C 0.6969(4) 0.3303(3) 0.8517(3) 0.0171(7) Uani 1 1 d . . . H14 H 0.6926 0.3767 0.8028 0.021 Uiso 1 1 calc R . . C15 C 0.5795(4) 0.3195(3) 0.9124(3) 0.0177(7) Uani 1 1 d . . . H15 H 0.4970 0.3580 0.9044 0.021 Uiso 1 1 calc R . . C16 C 0.5840(4) 0.2529(3) 0.9837(3) 0.0155(7) Uani 1 1 d . . . C17 C 0.7085(4) 0.1984(3) 0.9931(3) 0.0171(7) Uani 1 1 d . . . H17 H 0.7165 0.1519 1.0419 0.020 Uiso 1 1 calc R . . C18 C 0.8190(4) 0.2135(3) 0.9303(3) 0.0180(8) Uani 1 1 d . . . H18 H 0.9033 0.1764 0.9370 0.022 Uiso 1 1 calc R . . C19 C 0.4614(4) 0.2367(3) 1.0523(3) 0.0190(8) Uani 1 1 d . . . H19A H 0.4406 0.1751 1.0534 0.023 Uiso 1 1 calc R . . H19B H 0.4972 0.2549 1.1274 0.023 Uiso 1 1 calc R . . C20 C 0.2681(4) 0.3545(3) 1.0473(3) 0.0184(8) Uani 1 1 d . . . H20 H 0.3092 0.3867 1.1089 0.022 Uiso 1 1 calc R . . C21 C 0.1407(4) 0.3723(3) 0.9752(3) 0.0173(8) Uani 1 1 d . . . C22 C 0.0307(4) 0.4432(3) 0.9788(3) 0.0190(8) Uani 1 1 d . . . H22A H -0.0363 0.4464 0.9085 0.023 Uiso 1 1 calc R . . H22B H 0.0866 0.4974 0.9896 0.023 Uiso 1 1 calc R . . C23 C -0.0654(5) 0.4322(3) 1.0688(3) 0.0210(8) Uani 1 1 d . . . H23A H 0.0006 0.4353 1.1395 0.025 Uiso 1 1 calc R . . H23B H -0.1123 0.3753 1.0626 0.025 Uiso 1 1 calc R . . C24 C -0.1894(5) 0.4993(3) 1.0653(3) 0.0226(8) Uani 1 1 d . . . H24A H -0.1422 0.5559 1.0778 0.027 Uiso 1 1 calc R . . H24B H -0.2502 0.4995 0.9925 0.027 Uiso 1 1 calc R . . C25 C -0.2935(5) 0.4838(3) 1.1496(3) 0.0237(9) Uani 1 1 d . . . H25A H -0.3373 0.4262 1.1394 0.028 Uiso 1 1 calc R . . H25B H -0.2338 0.4865 1.2227 0.028 Uiso 1 1 calc R . . C26 C -0.4197(5) 0.5482(3) 1.1416(4) 0.0316(10) Uani 1 1 d . . . H26A H -0.3769 0.6053 1.1526 0.047 Uiso 1 1 calc R . . H26B H -0.4833 0.5363 1.1970 0.047 Uiso 1 1 calc R . . H26C H -0.4807 0.5448 1.0699 0.047 Uiso 1 1 calc R . . Cl1 Cl 0.43164(12) 0.38349(7) 0.35293(7) 0.0258(2) Uani 1 1 d . . . O1 O 0.5758(4) 0.4232(2) 0.3856(3) 0.0377(8) Uani 1 1 d . . . O2 O 0.3696(5) 0.3603(4) 0.4467(3) 0.0605(14) Uani 1 1 d . . . O3 O 0.3319(4) 0.4420(2) 0.2886(2) 0.0318(7) Uani 1 1 d . . . O4 O 0.4499(7) 0.3106(3) 0.2901(3) 0.0713(16) Uani 1 1 d . . . O1W O 0.9564(3) 0.4168(2) 0.7139(2) 0.0228(6) Uani 1 1 d D . . H1WA H 0.882(4) 0.440(3) 0.672(3) 0.027 Uiso 1 1 d D . . H1WB H 1.026(4) 0.452(3) 0.708(4) 0.027 Uiso 1 1 d D . . O2W O 0.3172(4) 0.9623(3) 0.3948(3) 0.0370(8) Uani 1 1 d . . . H2WA H 0.345(7) 0.935(4) 0.453(5) 0.044 Uiso 1 1 d . . . H2WB H 0.407(7) 0.966(4) 0.370(5) 0.044 Uiso 1 1 d . . . O1S O 0.0878(6) 0.5100(4) 0.3863(5) 0.0523(17) Uani 0.723(6) 1 d PD . . H1S H 0.1527 0.4827 0.3586 0.078 Uiso 0.723(6) 1 calc PR . . C1S C 0.1275(8) 0.5146(4) 0.4879(7) 0.0395(18) Uani 0.723(6) 1 d PD . . H1S1 H 0.1967 0.5625 0.5048 0.059 Uiso 0.723(6) 1 calc PR . . H1S2 H 0.1783 0.4620 0.5141 0.059 Uiso 0.723(6) 1 calc PR . . H1S3 H 0.0382 0.5229 0.5232 0.059 Uiso 0.723(6) 1 calc PR . . 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 Cl2 0.0347(6) 0.0213(5) 0.0286(5) 0.0023(4) 0.0126(4) 0.0020(4) O5 0.074(2) 0.0472(18) 0.0600(18) 0.0052(14) -0.0015(15) 0.0095(15) O6 0.074(2) 0.0472(18) 0.0600(18) 0.0052(14) -0.0015(15) 0.0095(15) O7 0.074(2) 0.0472(18) 0.0600(18) 0.0052(14) -0.0015(15) 0.0095(15) O8 0.074(2) 0.0472(18) 0.0600(18) 0.0052(14) -0.0015(15) 0.0095(15) Cu1 0.00938(18) 0.0202(2) 0.01468(19) -0.00016(19) 0.00348(13) 0.00058(19) N1 0.0116(14) 0.0195(18) 0.0234(16) 0.0001(14) 0.0041(12) -0.0014(13) N2 0.0137(15) 0.0236(18) 0.0155(14) -0.0051(13) 0.0036(12) 0.0001(13) N3 0.0125(15) 0.0235(18) 0.0180(14) -0.0045(13) 0.0036(12) -0.0002(13) N4 0.0097(14) 0.0223(17) 0.0206(15) -0.0018(13) 0.0036(11) 0.0011(13) N5 0.0108(12) 0.0231(18) 0.0142(12) 0.0012(14) 0.0020(10) -0.0014(14) N6 0.0110(12) 0.0254(17) 0.0172(13) 0.0066(16) 0.0049(10) 0.0020(15) N7 0.0129(15) 0.0227(17) 0.0179(14) 0.0029(13) 0.0033(12) 0.0011(13) N8 0.0132(14) 0.0223(19) 0.0165(13) 0.0005(12) 0.0042(11) 0.0046(12) C1 0.0159(15) 0.0170(17) 0.0178(15) -0.0043(18) 0.0001(12) -0.0023(18) C2 0.0143(17) 0.0203(19) 0.0177(17) 0.0030(15) 0.0027(13) -0.0028(15) C3 0.0134(17) 0.025(2) 0.0161(16) -0.0027(15) 0.0032(13) -0.0003(15) C4 0.0194(19) 0.0154(19) 0.0230(18) -0.0020(16) 0.0048(15) -0.0025(15) C5 0.0116(17) 0.021(2) 0.0240(19) 0.0024(16) 0.0029(14) -0.0008(15) C6 0.0152(18) 0.026(2) 0.030(2) -0.0155(18) 0.0087(16) -0.0058(16) C7 0.0162(18) 0.027(2) 0.0189(17) 0.0035(17) 0.0057(14) 0.0064(16) C8 0.0168(16) 0.023(2) 0.0123(15) -0.0005(14) 0.0053(12) 0.0064(14) C9 0.023(2) 0.026(2) 0.0198(18) 0.0034(17) 0.0053(15) 0.0018(17) C10 0.026(2) 0.032(3) 0.0149(16) 0.0046(16) 0.0066(14) 0.0021(17) C11 0.024(2) 0.027(2) 0.0210(18) 0.0028(17) 0.0067(15) -0.0008(17) C12 0.036(2) 0.045(3) 0.023(2) -0.007(2) 0.0121(19) -0.003(2) C13 0.074(4) 0.032(3) 0.048(3) -0.013(3) 0.037(3) -0.008(3) C14 0.0164(18) 0.018(2) 0.0173(16) 0.0024(15) 0.0034(14) 0.0002(15) C15 0.0134(17) 0.0235(19) 0.0170(16) 0.0030(15) 0.0044(13) 0.0048(15) C16 0.0127(16) 0.0222(19) 0.0116(15) 0.0001(14) 0.0018(12) -0.0005(14) C17 0.0168(17) 0.0193(19) 0.0150(16) 0.0052(15) 0.0019(13) 0.0008(15) C18 0.0123(16) 0.019(2) 0.0233(18) 0.0057(16) 0.0038(14) 0.0045(15) C19 0.0149(17) 0.025(2) 0.0176(17) 0.0057(16) 0.0034(13) 0.0042(15) C20 0.0156(18) 0.022(2) 0.0180(17) -0.0005(15) 0.0033(14) 0.0006(15) C21 0.0172(18) 0.021(2) 0.0141(16) 0.0030(15) 0.0047(13) -0.0019(15) C22 0.0141(18) 0.019(2) 0.0233(18) -0.0028(16) 0.0025(14) 0.0000(15) C23 0.021(2) 0.023(2) 0.0202(18) 0.0000(16) 0.0066(15) 0.0028(16) C24 0.025(2) 0.021(2) 0.0227(19) -0.0029(17) 0.0062(16) 0.0019(17) C25 0.027(2) 0.025(2) 0.0215(18) -0.0012(17) 0.0123(16) 0.0030(17) C26 0.036(3) 0.028(3) 0.033(2) 0.005(2) 0.013(2) 0.010(2) Cl1 0.0341(5) 0.0234(5) 0.0180(4) 0.0003(4) -0.0022(4) 0.0004(4) O1 0.0346(18) 0.042(2) 0.0340(17) 0.0089(16) -0.0025(14) -0.0020(16) O2 0.045(2) 0.092(4) 0.043(2) 0.037(2) 0.0015(18) -0.010(2) O3 0.0354(18) 0.0340(19) 0.0242(15) 0.0015(14) -0.0012(13) 0.0087(15) O4 0.109(4) 0.042(3) 0.048(2) -0.0208(19) -0.038(2) 0.036(3) O1W 0.0238(15) 0.0208(16) 0.0229(14) 0.0047(12) 0.0008(12) -0.0002(12) O2W 0.0313(18) 0.050(2) 0.0288(17) 0.0044(17) 0.0000(14) -0.0107(17) O1S 0.040(3) 0.038(3) 0.085(4) 0.018(3) 0.030(3) 0.026(3) C1S 0.024(3) 0.018(3) 0.080(6) -0.014(3) 0.016(3) -0.006(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 Cl2 O7A 1.361(10) . ? Cl2 O8 1.368(6) . ? Cl2 O5 1.373(5) . ? Cl2 O6 1.421(7) . ? Cl2 O6A 1.444(10) . ? Cl2 O7 1.490(6) . ? Cl2 O8A 1.590(10) . ? Cu1 N1 2.003(3) . ? Cu1 N4 2.016(3) 1_455 ? Cu1 N5 2.017(3) . ? Cu1 N8 2.025(3) 1_655 ? Cu1 O1W 2.175(3) . ? N1 C5 1.338(5) . ? N1 C1 1.342(5) . ? N2 N3 1.335(4) . ? N2 C7 1.348(5) . ? N2 C6 1.459(5) . ? N3 N4 1.325(5) . ? N4 C8 1.377(5) . ? N4 Cu1 2.016(3) 1_655 ? N5 C14 1.329(5) . ? N5 C18 1.343(5) . ? N6 N7 1.333(4) . ? N6 C20 1.352(6) . ? N6 C19 1.455(5) . ? N7 N8 1.328(5) . ? N8 C21 1.368(5) . ? N8 Cu1 2.025(3) 1_455 ? C1 C2 1.374(5) . ? C2 C3 1.374(6) . ? C3 C4 1.387(5) . ? C3 C6 1.522(5) . ? C4 C5 1.397(6) . ? C7 C8 1.378(6) . ? C8 C9 1.482(6) . ? C9 C10 1.544(5) . ? C10 C11 1.527(6) . ? C11 C12 1.521(5) . ? C12 C13 1.522(8) . ? C14 C15 1.398(5) . ? C15 C16 1.376(5) . ? C16 C17 1.400(5) . ? C16 C19 1.515(5) . ? C17 C18 1.375(5) . ? C20 C21 1.376(5) . ? C21 C22 1.496(6) . ? C22 C23 1.527(5) . ? C23 C24 1.531(6) . ? C24 C25 1.529(5) . ? C25 C26 1.513(6) . ? Cl1 O4 1.416(4) . ? Cl1 O2 1.420(4) . ? Cl1 O1 1.440(4) . ? Cl1 O3 1.444(3) . ? O1S C1S 1.271(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 O7A Cl2 O8 64.9(6) . . ? O7A Cl2 O5 122.4(6) . . ? O8 Cl2 O5 113.2(4) . . ? O7A Cl2 O6 118.9(6) . . ? O8 Cl2 O6 110.8(4) . . ? O5 Cl2 O6 114.8(4) . . ? O7A Cl2 O6A 111.0(7) . . ? O8 Cl2 O6A 122.4(5) . . ? O5 Cl2 O6A 114.5(5) . . ? O6 Cl2 O6A 16.6(5) . . ? O7A Cl2 O7 43.2(6) . . ? O8 Cl2 O7 108.0(4) . . ? O5 Cl2 O7 102.8(3) . . ? O6 Cl2 O7 106.6(4) . . ? O6A Cl2 O7 90.9(5) . . ? O7A Cl2 O8A 103.5(6) . . ? O8 Cl2 O8A 39.9(5) . . ? O5 Cl2 O8A 101.2(5) . . ? O6 Cl2 O8A 83.9(6) . . ? O6A Cl2 O8A 100.1(6) . . ? O7 Cl2 O8A 146.4(5) . . ? N1 Cu1 N4 88.82(13) . 1_455 ? N1 Cu1 N5 154.85(14) . . ? N4 Cu1 N5 90.58(12) 1_455 . ? N1 Cu1 N8 89.87(13) . 1_655 ? N4 Cu1 N8 174.92(15) 1_455 1_655 ? N5 Cu1 N8 88.52(12) . 1_655 ? N1 Cu1 O1W 104.35(13) . . ? N4 Cu1 O1W 90.53(13) 1_455 . ? N5 Cu1 O1W 100.80(14) . . ? N8 Cu1 O1W 94.55(13) 1_655 . ? C5 N1 C1 118.7(3) . . ? C5 N1 Cu1 119.4(3) . . ? C1 N1 Cu1 121.9(3) . . ? N3 N2 C7 111.9(3) . . ? N3 N2 C6 118.8(3) . . ? C7 N2 C6 129.3(3) . . ? N4 N3 N2 105.7(3) . . ? N3 N4 C8 110.9(3) . . ? N3 N4 Cu1 116.3(2) . 1_655 ? C8 N4 Cu1 132.7(3) . 1_655 ? C14 N5 C18 117.9(3) . . ? C14 N5 Cu1 123.8(3) . . ? C18 N5 Cu1 118.2(3) . . ? N7 N6 C20 111.8(3) . . ? N7 N6 C19 118.8(4) . . ? C20 N6 C19 129.2(3) . . ? N8 N7 N6 106.0(3) . . ? N7 N8 C21 110.3(3) . . ? N7 N8 Cu1 115.9(2) . 1_455 ? C21 N8 Cu1 133.8(3) . 1_455 ? N1 C1 C2 122.4(4) . . ? C3 C2 C1 119.7(4) . . ? C2 C3 C4 118.5(4) . . ? C2 C3 C6 123.8(4) . . ? C4 C3 C6 117.7(4) . . ? C3 C4 C5 119.0(4) . . ? N1 C5 C4 121.7(4) . . ? N2 C6 C3 111.8(3) . . ? N2 C7 C8 105.9(3) . . ? N4 C8 C7 105.6(3) . . ? N4 C8 C9 125.2(3) . . ? C7 C8 C9 129.1(3) . . ? C8 C9 C10 113.7(4) . . ? C11 C10 C9 113.9(3) . . ? C12 C11 C10 111.5(4) . . ? C11 C12 C13 113.8(4) . . ? N5 C14 C15 122.4(4) . . ? C16 C15 C14 119.6(4) . . ? C15 C16 C17 118.0(3) . . ? C15 C16 C19 122.9(3) . . ? C17 C16 C19 119.1(3) . . ? C18 C17 C16 118.6(4) . . ? N5 C18 C17 123.5(3) . . ? N6 C19 C16 112.1(3) . . ? N6 C20 C21 105.3(3) . . ? N8 C21 C20 106.7(4) . . ? N8 C21 C22 125.0(3) . . ? C20 C21 C22 128.3(4) . . ? C21 C22 C23 112.6(3) . . ? C22 C23 C24 112.9(3) . . ? C25 C24 C23 112.7(4) . . ? C26 C25 C24 112.0(4) . . ? O4 Cl1 O2 110.0(3) . . ? O4 Cl1 O1 109.7(3) . . ? O2 Cl1 O1 108.9(2) . . ? O4 Cl1 O3 108.8(2) . . ? O2 Cl1 O3 109.8(2) . . ? O1 Cl1 O3 109.6(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O2W 0.86(2) 1.89(3) 2.719(5) 160(5) 2_646 O1W H1WB O8A 0.85(2) 2.04(2) 2.875(12) 170(5) 2_756 O1W H1WB O8 0.85(2) 2.04(3) 2.825(7) 154(5) 2_756 O2W H2WA O1 0.86(7) 2.04(6) 2.841(5) 155(6) 2_656 O2W H2WB O6A 0.90(7) 1.92(7) 2.777(11) 158(6) 1_565 O2W H2WB O6 0.90(7) 1.95(7) 2.846(8) 170(6) 1_565 O1S H1S O3 0.84 2.05 2.871(6) 167.2 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.734 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.101 #===end data_a210 _database_code_depnum_ccdc_archive 'CCDC 772011' #TrackingRef '- CEC-CIF-29Jun2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H46 Cl2 Cu N8 O11' _chemical_formula_weight 805.17 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.9908(13) _cell_length_b 15.880(2) _cell_length_c 12.7955(18) _cell_angle_alpha 90.00 _cell_angle_beta 100.110(3) _cell_angle_gamma 90.00 _cell_volume 1798.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 920 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 27.47 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 842 _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6649 _exptl_absorpt_correction_T_max 0.8527 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12764 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7433 _reflns_number_gt 6901 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0595P)^2^+0.2025P] 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 0.019(12) _refine_ls_number_reflns 7433 _refine_ls_number_parameters 471 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.00405(4) 0.62325(3) 0.71753(3) 0.01871(11) Uani 1 1 d . . . N1 N -0.1566(3) 0.60023(19) 0.5891(2) 0.0208(6) Uani 1 1 d . . . N2 N -0.2645(3) 0.65685(19) 0.5669(2) 0.0186(6) Uani 1 1 d . . . N3 N -0.3512(3) 0.6316(2) 0.4769(2) 0.0193(6) Uani 1 1 d . . . N4 N -0.8412(3) 0.6276(2) 0.6196(2) 0.0204(5) Uani 1 1 d . . . N5 N 0.1607(3) 0.65967(19) 0.8404(2) 0.0187(6) Uani 1 1 d . . . N6 N 0.2636(3) 0.7140(2) 0.8224(2) 0.0196(6) Uani 1 1 d . . . N7 N 0.3488(3) 0.72903(19) 0.9164(2) 0.0185(6) Uani 1 1 d . . . N8 N 0.8440(3) 0.66976(19) 0.7937(2) 0.0190(6) Uani 1 1 d . . . Cl2 Cl 0.32357(10) 0.86818(6) 0.22122(7) 0.0278(2) Uani 1 1 d . . . O1 O 0.6164(4) 0.5665(2) 0.0499(2) 0.0446(8) Uani 1 1 d . . . O2 O 0.6600(3) 0.4721(2) 0.1944(2) 0.0353(7) Uani 1 1 d . . . O3 O 0.5173(4) 0.5943(2) 0.2034(2) 0.0471(9) Uani 1 1 d . . . O4 O 0.4180(3) 0.48396(18) 0.0912(2) 0.0312(6) Uani 1 1 d . . . C1 C -0.3008(4) 0.5592(2) 0.4410(3) 0.0228(7) Uani 1 1 d . . . H1 H -0.3430 0.5293 0.3785 0.027 Uiso 1 1 calc R . . C2 C -0.1762(4) 0.5378(2) 0.5133(3) 0.0235(7) Uani 1 1 d . . . C3 C -0.4905(4) 0.6759(3) 0.4375(3) 0.0236(7) Uani 1 1 d . . . H3A H -0.5262 0.6601 0.3624 0.028 Uiso 1 1 calc R . . H3B H -0.4708 0.7373 0.4400 0.028 Uiso 1 1 calc R . . C4 C -0.8587(4) 0.6830(3) 0.5402(3) 0.0258(8) Uani 1 1 d . . . H4 H -0.9524 0.7119 0.5236 0.031 Uiso 1 1 calc R . . C5 C -0.7487(4) 0.7008(3) 0.4805(3) 0.0269(8) Uani 1 1 d . . . H5 H -0.7651 0.7425 0.4265 0.032 Uiso 1 1 calc R . . C6 C -0.6128(4) 0.6562(2) 0.5012(3) 0.0202(7) Uani 1 1 d . . . C7 C -0.5978(4) 0.5956(2) 0.5801(3) 0.0199(7) Uani 1 1 d . . . H7 H -0.5092 0.5619 0.5941 0.024 Uiso 1 1 calc R . . C8 C -0.7115(4) 0.5842(2) 0.6383(3) 0.0211(7) Uani 1 1 d . . . H8 H -0.6973 0.5438 0.6940 0.025 Uiso 1 1 calc R . . C9 C -0.0829(5) 0.4581(3) 0.5189(3) 0.0342(9) Uani 1 1 d . . . H9A H -0.1259 0.4160 0.5623 0.041 Uiso 1 1 calc R . . H9B H 0.0213 0.4707 0.5551 0.041 Uiso 1 1 calc R . . C10 C -0.0771(5) 0.4204(3) 0.4107(4) 0.0397(10) Uani 1 1 d . . . H10A H -0.0709 0.3583 0.4174 0.048 Uiso 1 1 calc R . . H10B H -0.1720 0.4343 0.3619 0.048 Uiso 1 1 calc R . . C11 C 0.0549(6) 0.4516(3) 0.3633(4) 0.0418(11) Uani 1 1 d . . . H11A H 0.0329 0.4430 0.2855 0.050 Uiso 1 1 calc R . . H11B H 0.0677 0.5127 0.3769 0.050 Uiso 1 1 calc R . . C12 C 0.1995(6) 0.4071(3) 0.4083(3) 0.0409(11) Uani 1 1 d . . . H12A H 0.1828 0.3456 0.4014 0.049 Uiso 1 1 calc R . . H12B H 0.2260 0.4202 0.4850 0.049 Uiso 1 1 calc R . . C13 C 0.3314(7) 0.4305(3) 0.3553(4) 0.0478(13) Uani 1 1 d . . . H13A H 0.3604 0.4897 0.3730 0.057 Uiso 1 1 calc R . . H13B H 0.2998 0.4267 0.2774 0.057 Uiso 1 1 calc R . . C14 C 0.4674(7) 0.3742(3) 0.3894(5) 0.0587(16) Uani 1 1 d . . . H14A H 0.5007 0.3788 0.4663 0.088 Uiso 1 1 calc R . . H14B H 0.5496 0.3917 0.3530 0.088 Uiso 1 1 calc R . . H14C H 0.4399 0.3157 0.3708 0.088 Uiso 1 1 calc R . . C15 C 0.3022(4) 0.6855(2) 0.9949(3) 0.0204(7) Uani 1 1 d . . . H15 H 0.3454 0.6862 1.0682 0.025 Uiso 1 1 calc R . . C16 C 0.1812(4) 0.6405(2) 0.9479(3) 0.0203(7) Uani 1 1 d . . . C17 C 0.4809(4) 0.7836(2) 0.9215(3) 0.0236(7) Uani 1 1 d . . . H17A H 0.5173 0.8001 0.9962 0.028 Uiso 1 1 calc R . . H17B H 0.4512 0.8355 0.8803 0.028 Uiso 1 1 calc R . . C18 C 0.7210(3) 0.6245(3) 0.8025(2) 0.0194(6) Uani 1 1 d . . . H18 H 0.7156 0.5675 0.7798 0.023 Uiso 1 1 calc R . . C19 C 0.6018(4) 0.6583(2) 0.8434(3) 0.0188(7) Uani 1 1 d . . . H19 H 0.5155 0.6248 0.8477 0.023 Uiso 1 1 calc R . . C20 C 0.6085(4) 0.7410(2) 0.8781(3) 0.0175(6) Uani 1 1 d . . . C21 C 0.7377(4) 0.7868(2) 0.8720(3) 0.0216(7) Uani 1 1 d . . . H21 H 0.7467 0.8434 0.8964 0.026 Uiso 1 1 calc R . . C22 C 0.8546(4) 0.7494(2) 0.8297(3) 0.0205(7) Uani 1 1 d . . . H22 H 0.9434 0.7809 0.8264 0.025 Uiso 1 1 calc R . . C23 C 0.0867(4) 0.5775(2) 0.9954(3) 0.0237(7) Uani 1 1 d . . . H23A H 0.1367 0.5218 0.9987 0.028 Uiso 1 1 calc R . . H23B H -0.0130 0.5722 0.9486 0.028 Uiso 1 1 calc R . . C24 C 0.0632(4) 0.6024(2) 1.1071(3) 0.0256(8) Uani 1 1 d . . . H24A H 0.0210 0.5538 1.1405 0.031 Uiso 1 1 calc R . . H24B H 0.1622 0.6164 1.1508 0.031 Uiso 1 1 calc R . . C25 C -0.0423(4) 0.6772(2) 1.1063(3) 0.0237(7) Uani 1 1 d . . . H25A H 0.0033 0.7267 1.0771 0.028 Uiso 1 1 calc R . . H25B H -0.1389 0.6645 1.0587 0.028 Uiso 1 1 calc R . . C26 C -0.0744(4) 0.6990(3) 1.2156(3) 0.0280(8) Uani 1 1 d . . . H26A H -0.1109 0.6480 1.2476 0.034 Uiso 1 1 calc R . . H26B H 0.0208 0.7169 1.2613 0.034 Uiso 1 1 calc R . . C27 C -0.1903(5) 0.7680(3) 1.2131(3) 0.0303(8) Uani 1 1 d . . . H27A H -0.2897 0.7466 1.1773 0.036 Uiso 1 1 calc R . . H27B H -0.1622 0.8156 1.1706 0.036 Uiso 1 1 calc R . . C28 C -0.2051(5) 0.8000(3) 1.3225(3) 0.0342(9) Uani 1 1 d . . . H28A H -0.2298 0.7530 1.3660 0.051 Uiso 1 1 calc R . . H28B H -0.2856 0.8423 1.3160 0.051 Uiso 1 1 calc R . . H28C H -0.1093 0.8255 1.3564 0.051 Uiso 1 1 calc R . . Cl1 Cl 0.55377(10) 0.52979(6) 0.13442(6) 0.02427(18) Uani 1 1 d . . . O5 O 0.4284(4) 0.8562(2) 0.1492(3) 0.0488(9) Uani 1 1 d . . . O6 O 0.2979(5) 0.7885(3) 0.2637(4) 0.0705(12) Uani 1 1 d . . . O7 O 0.1852(4) 0.9000(3) 0.1601(3) 0.0528(10) Uani 1 1 d . . . O8 O 0.3799(5) 0.9250(3) 0.2993(3) 0.0599(10) Uani 1 1 d . . . O1W O 0.0428(3) 0.49117(18) 0.7630(2) 0.0247(5) Uani 1 1 d D . . H1W H -0.009(4) 0.455(2) 0.783(3) 0.030 Uiso 1 1 d D . . H2W H 0.117(3) 0.486(3) 0.810(3) 0.030 Uiso 1 1 d D . . O2W O 0.6636(3) 0.9733(2) 0.1343(2) 0.0301(6) Uani 1 1 d D . . H3W H 0.610(5) 0.931(2) 0.124(3) 0.036 Uiso 1 1 d D . . H4W H 0.641(5) 0.989(3) 0.0701(19) 0.036 Uiso 1 1 d D . . O3W O 0.8866(4) 0.3873(2) 0.0785(3) 0.0405(7) Uani 1 1 d D . . H5W H 0.818(5) 0.417(3) 0.093(4) 0.049 Uiso 1 1 d D . . H6W H 0.866(6) 0.397(3) 0.0130(17) 0.049 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01019(17) 0.0277(2) 0.01894(19) -0.00073(18) 0.00441(13) 0.00120(18) N1 0.0118(13) 0.0307(18) 0.0208(14) 0.0001(11) 0.0051(11) 0.0015(11) N2 0.0143(14) 0.0244(14) 0.0186(14) -0.0005(11) 0.0070(11) -0.0015(11) N3 0.0141(12) 0.0282(15) 0.0171(12) 0.0009(13) 0.0068(9) -0.0001(13) N4 0.0145(12) 0.0281(14) 0.0188(13) 0.0003(14) 0.0037(9) 0.0004(14) N5 0.0114(13) 0.0253(14) 0.0211(14) -0.0006(11) 0.0073(11) -0.0003(11) N6 0.0115(13) 0.0273(15) 0.0204(14) -0.0004(12) 0.0039(10) 0.0005(12) N7 0.0114(12) 0.0218(14) 0.0230(15) -0.0028(11) 0.0045(11) 0.0032(11) N8 0.0098(13) 0.0269(16) 0.0209(14) 0.0011(12) 0.0042(10) 0.0039(11) Cl2 0.0250(4) 0.0307(5) 0.0292(5) 0.0073(4) 0.0093(3) 0.0057(4) O1 0.0415(18) 0.062(2) 0.0299(16) 0.0119(14) 0.0047(13) -0.0166(16) O2 0.0338(15) 0.0385(16) 0.0313(15) 0.0008(12) -0.0010(12) 0.0039(13) O3 0.064(2) 0.0444(19) 0.0279(16) -0.0093(13) -0.0061(14) 0.0146(16) O4 0.0294(14) 0.0336(15) 0.0312(15) 0.0008(12) 0.0072(11) -0.0010(12) C1 0.0187(17) 0.0283(19) 0.0214(18) -0.0038(14) 0.0032(14) 0.0016(15) C2 0.0205(17) 0.0282(19) 0.0229(17) -0.0061(15) 0.0069(13) 0.0018(15) C3 0.0167(16) 0.037(2) 0.0176(17) 0.0027(14) 0.0032(12) 0.0025(15) C4 0.0133(16) 0.037(2) 0.0269(19) 0.0033(16) 0.0036(13) 0.0088(15) C5 0.0217(18) 0.037(2) 0.0218(18) 0.0069(15) 0.0042(14) 0.0067(16) C6 0.0138(15) 0.0314(18) 0.0150(16) -0.0028(13) 0.0012(12) -0.0005(13) C7 0.0128(15) 0.0259(17) 0.0213(17) 0.0005(13) 0.0042(12) 0.0028(12) C8 0.0183(16) 0.0278(18) 0.0168(16) 0.0017(14) 0.0017(12) 0.0001(14) C9 0.030(2) 0.036(2) 0.034(2) -0.0036(17) -0.0025(16) 0.0109(18) C10 0.037(2) 0.037(2) 0.041(3) -0.0128(19) -0.0043(19) 0.007(2) C11 0.059(3) 0.038(2) 0.027(2) 0.0014(18) 0.004(2) 0.001(2) C12 0.062(3) 0.033(2) 0.028(2) 0.0023(17) 0.009(2) -0.005(2) C13 0.078(4) 0.036(2) 0.035(3) -0.0038(19) 0.025(2) -0.014(3) C14 0.073(4) 0.030(2) 0.085(4) -0.006(3) 0.049(3) -0.006(3) C15 0.0229(17) 0.0200(16) 0.0198(17) 0.0017(13) 0.0077(13) 0.0071(14) C16 0.0194(16) 0.0222(19) 0.0218(16) 0.0002(13) 0.0101(13) 0.0029(13) C17 0.0162(16) 0.0247(17) 0.0305(19) -0.0087(15) 0.0062(14) -0.0020(14) C18 0.0155(13) 0.0231(15) 0.0199(14) 0.0027(15) 0.0042(11) 0.0002(17) C19 0.0115(15) 0.0269(17) 0.0182(16) 0.0037(13) 0.0030(12) -0.0007(13) C20 0.0131(14) 0.0227(16) 0.0161(15) 0.0044(13) 0.0010(12) 0.0043(13) C21 0.0183(16) 0.0218(17) 0.0250(18) -0.0017(14) 0.0047(13) 0.0002(14) C22 0.0130(15) 0.0266(18) 0.0223(17) 0.0037(14) 0.0039(12) -0.0035(13) C23 0.0212(17) 0.0271(19) 0.0237(18) 0.0025(14) 0.0067(14) -0.0014(15) C24 0.0256(18) 0.028(2) 0.0245(18) 0.0018(14) 0.0085(14) -0.0016(14) C25 0.0225(18) 0.0296(19) 0.0195(17) 0.0020(14) 0.0049(13) 0.0001(15) C26 0.0269(19) 0.038(2) 0.0212(18) 0.0024(16) 0.0096(14) -0.0005(17) C27 0.033(2) 0.032(2) 0.026(2) -0.0022(16) 0.0067(16) 0.0059(17) C28 0.037(2) 0.036(2) 0.032(2) -0.0026(17) 0.0150(17) 0.0004(18) Cl1 0.0278(4) 0.0272(4) 0.0171(4) 0.0012(3) 0.0018(3) -0.0002(4) O5 0.0431(19) 0.059(2) 0.051(2) -0.0201(17) 0.0248(16) -0.0151(17) O6 0.078(3) 0.057(2) 0.076(3) 0.034(2) 0.013(2) -0.006(2) O7 0.0436(19) 0.073(3) 0.0386(18) -0.0034(17) -0.0011(14) 0.0330(18) O8 0.071(3) 0.066(2) 0.042(2) -0.0095(18) 0.0055(18) 0.022(2) O1W 0.0178(12) 0.0324(14) 0.0230(13) 0.0011(11) 0.0007(10) -0.0014(11) O2W 0.0229(13) 0.0414(16) 0.0246(14) 0.0072(12) 0.0003(10) -0.0077(12) O3W 0.0371(17) 0.048(2) 0.0359(17) 0.0034(14) 0.0038(13) 0.0132(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N5 2.003(3) . ? Cu1 N8 2.014(3) 1_455 ? Cu1 N1 2.021(3) . ? Cu1 N4 2.030(3) 1_655 ? Cu1 O1W 2.188(3) . ? N1 N2 1.317(4) . ? N1 C2 1.376(5) . ? N2 N3 1.334(4) . ? N3 C1 1.345(5) . ? N3 C3 1.448(4) . ? N4 C4 1.332(5) . ? N4 C8 1.340(5) . ? N4 Cu1 2.030(3) 1_455 ? N5 N6 1.315(4) . ? N5 C16 1.390(4) . ? N6 N7 1.329(4) . ? N7 C15 1.346(5) . ? N7 C17 1.463(5) . ? N8 C18 1.340(4) . ? N8 C22 1.344(5) . ? N8 Cu1 2.014(3) 1_655 ? Cl2 O8 1.375(4) . ? Cl2 O6 1.411(4) . ? Cl2 O7 1.440(3) . ? Cl2 O5 1.442(3) . ? O1 Cl1 1.428(3) . ? O2 Cl1 1.443(3) . ? O3 Cl1 1.428(3) . ? O4 Cl1 1.445(3) . ? C1 C2 1.365(5) . ? C2 C9 1.513(5) . ? C3 C6 1.512(5) . ? C4 C5 1.381(5) . ? C5 C6 1.397(5) . ? C6 C7 1.384(5) . ? C7 C8 1.379(5) . ? C9 C10 1.517(6) . ? C10 C11 1.508(7) . ? C11 C12 1.503(7) . ? C12 C13 1.513(7) . ? C13 C14 1.516(9) . ? C15 C16 1.351(5) . ? C16 C23 1.508(5) . ? C17 C20 1.518(5) . ? C18 C19 1.381(5) . ? C19 C20 1.384(5) . ? C20 C21 1.385(5) . ? C21 C22 1.396(5) . ? C23 C24 1.533(5) . ? C24 C25 1.518(5) . ? C25 C26 1.516(5) . ? C26 C27 1.508(6) . ? C27 C28 1.517(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 N5 Cu1 N8 88.74(12) . 1_455 ? N5 Cu1 N1 173.61(13) . . ? N8 Cu1 N1 89.46(12) 1_455 . ? N5 Cu1 N4 90.63(11) . 1_655 ? N8 Cu1 N4 155.64(13) 1_455 1_655 ? N1 Cu1 N4 88.49(11) . 1_655 ? N5 Cu1 O1W 90.62(11) . . ? N8 Cu1 O1W 108.46(11) 1_455 . ? N1 Cu1 O1W 95.77(11) . . ? N4 Cu1 O1W 95.90(12) 1_655 . ? N2 N1 C2 109.9(3) . . ? N2 N1 Cu1 116.5(2) . . ? C2 N1 Cu1 133.5(2) . . ? N1 N2 N3 106.1(3) . . ? N2 N3 C1 111.7(3) . . ? N2 N3 C3 119.5(3) . . ? C1 N3 C3 128.3(3) . . ? C4 N4 C8 117.3(3) . . ? C4 N4 Cu1 119.4(2) . 1_455 ? C8 N4 Cu1 122.8(2) . 1_455 ? N6 N5 C16 110.0(3) . . ? N6 N5 Cu1 118.1(2) . . ? C16 N5 Cu1 131.8(2) . . ? N5 N6 N7 105.7(3) . . ? N6 N7 C15 112.2(3) . . ? N6 N7 C17 118.8(3) . . ? C15 N7 C17 128.9(3) . . ? C18 N8 C22 119.0(3) . . ? C18 N8 Cu1 120.9(2) . 1_655 ? C22 N8 Cu1 119.9(2) . 1_655 ? O8 Cl2 O6 111.9(3) . . ? O8 Cl2 O7 109.7(2) . . ? O6 Cl2 O7 109.9(3) . . ? O8 Cl2 O5 110.6(2) . . ? O6 Cl2 O5 107.3(3) . . ? O7 Cl2 O5 107.4(2) . . ? N3 C1 C2 105.5(3) . . ? C1 C2 N1 106.7(3) . . ? C1 C2 C9 128.5(3) . . ? N1 C2 C9 124.6(3) . . ? N3 C3 C6 112.3(3) . . ? N4 C4 C5 123.8(3) . . ? C4 C5 C6 118.6(3) . . ? C7 C6 C5 117.5(3) . . ? C7 C6 C3 123.3(3) . . ? C5 C6 C3 119.2(3) . . ? C8 C7 C6 120.0(3) . . ? N4 C8 C7 122.7(3) . . ? C2 C9 C10 113.2(4) . . ? C11 C10 C9 113.2(4) . . ? C12 C11 C10 112.4(4) . . ? C11 C12 C13 114.0(4) . . ? C12 C13 C14 112.5(4) . . ? N7 C15 C16 105.8(3) . . ? C15 C16 N5 106.3(3) . . ? C15 C16 C23 129.6(3) . . ? N5 C16 C23 123.9(3) . . ? N7 C17 C20 112.2(3) . . ? N8 C18 C19 122.1(4) . . ? C18 C19 C20 119.8(3) . . ? C19 C20 C21 118.0(3) . . ? C19 C20 C17 123.2(3) . . ? C21 C20 C17 118.7(3) . . ? C20 C21 C22 119.6(3) . . ? N8 C22 C21 121.4(3) . . ? C16 C23 C24 112.6(3) . . ? C25 C24 C23 112.6(3) . . ? C26 C25 C24 113.1(3) . . ? C27 C26 C25 112.9(3) . . ? C26 C27 C28 113.4(3) . . ? O3 Cl1 O1 109.8(2) . . ? O3 Cl1 O2 109.23(18) . . ? O1 Cl1 O2 110.5(2) . . ? O3 Cl1 O4 109.15(19) . . ? O1 Cl1 O4 109.55(18) . . ? O2 Cl1 O4 108.61(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3W H6W O7 0.839(19) 2.18(2) 3.015(5) 171(5) 2_645 O3W H5W O2 0.822(19) 2.26(2) 3.037(4) 158(5) . O2W H4W Cl1 0.849(19) 2.95(3) 3.754(3) 158(4) 2_655 O2W H4W O4 0.849(19) 2.04(3) 2.855(4) 160(4) 2_655 O2W H3W O5 0.829(19) 2.09(3) 2.847(4) 153(5) . O1W H2W O2W 0.815(19) 1.99(2) 2.749(4) 155(4) 2_646 O1W H1W O7 0.810(19) 2.05(2) 2.823(4) 160(4) 2_546 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.136 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.090 #===end data_a250 _database_code_depnum_ccdc_archive 'CCDC 773908' #TrackingRef '- CEC-CIF-29Jun2011.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H40 Cl2 Cu N8 O12' _chemical_formula_weight 767.08 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.911(8) _cell_length_b 10.004(9) _cell_length_c 19.252(17) _cell_angle_alpha 90.00 _cell_angle_beta 101.20(2) _cell_angle_gamma 90.00 _cell_volume 1684(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1609 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 24.13 _exptl_crystal_description NEEDLE _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.74 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 798 _exptl_absorpt_coefficient_mu 0.877 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5630 _exptl_absorpt_correction_T_max 0.9493 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9133 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2950 _reflns_number_gt 2295 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.1040P)^2^+0.7806P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2950 _refine_ls_number_parameters 227 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1862 _refine_ls_wR_factor_gt 0.1730 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 1.0000 0.5000 0.0407(3) Uani 1 2 d S . . N1 N 0.4201(4) 0.9578(4) 0.58895(18) 0.0315(9) Uani 1 1 d . . . N2 N 0.3058(4) 0.8730(4) 0.58155(18) 0.0327(9) Uani 1 1 d . . . N3 N 0.2717(4) 0.8600(4) 0.64435(17) 0.0272(8) Uani 1 1 d . . . C1 C 0.4577(5) 0.9984(4) 0.6579(2) 0.0318(10) Uani 1 1 d . . . C2 C 0.3617(5) 0.9359(5) 0.6923(2) 0.0303(10) Uani 1 1 d . . . H2 H 0.3582 0.9436 0.7407 0.036 Uiso 1 1 calc R . . C3 C 0.1434(5) 0.7750(5) 0.6524(2) 0.0357(11) Uani 1 1 d . . . H3A H 0.1441 0.7620 0.7029 0.043 Uiso 1 1 calc R . . H3B H 0.1555 0.6872 0.6315 0.043 Uiso 1 1 calc R . . C4 C -0.2736(5) 0.8043(5) 0.5732(2) 0.0346(11) Uani 1 1 d . . . H4 H -0.3601 0.7486 0.5668 0.042 Uiso 1 1 calc R . . C5 C -0.1341(5) 0.7523(5) 0.6053(2) 0.0323(10) Uani 1 1 d . . . H5 H -0.1250 0.6620 0.6188 0.039 Uiso 1 1 calc R . . C6 C -0.0090(5) 0.8346(5) 0.6170(2) 0.0282(10) Uani 1 1 d . . . C7 C -0.0277(5) 0.9663(4) 0.5961(2) 0.0289(10) Uani 1 1 d . . . H7 H 0.0564 1.0249 0.6048 0.035 Uiso 1 1 calc R . . C8 C -0.1667(5) 1.0119(5) 0.5629(2) 0.0310(10) Uani 1 1 d . . . H8 H -0.1766 1.1015 0.5480 0.037 Uiso 1 1 calc R . . C9 C 0.5871(5) 1.0915(5) 0.6863(2) 0.0372(11) Uani 1 1 d . . . H9A H 0.5482 1.1642 0.7120 0.045 Uiso 1 1 calc R . . H9B H 0.6250 1.1311 0.6465 0.045 Uiso 1 1 calc R . . C10 C 0.7189(5) 1.0250(5) 0.7352(3) 0.0395(12) Uani 1 1 d . . . H10A H 0.6828 0.9889 0.7763 0.047 Uiso 1 1 calc R . . H10B H 0.7558 0.9500 0.7104 0.047 Uiso 1 1 calc R . . C11 C 0.8496(6) 1.1199(6) 0.7603(3) 0.0488(13) Uani 1 1 d . . . H11A H 0.8875 1.1549 0.7194 0.059 Uiso 1 1 calc R . . H11B H 0.8131 1.1955 0.7848 0.059 Uiso 1 1 calc R . . C12 C 0.9778(8) 1.0507(8) 0.8096(4) 0.095(3) Uani 1 1 d . . . H12A H 0.9412 1.0188 0.8509 0.142 Uiso 1 1 calc R . . H12B H 1.0613 1.1131 0.8243 0.142 Uiso 1 1 calc R . . H12C H 1.0137 0.9756 0.7854 0.142 Uiso 1 1 calc R . . N4 N -0.2910(4) 0.9318(4) 0.55063(17) 0.0300(9) Uani 1 1 d . . . Cl1 Cl 0.33678(14) 0.83496(12) 0.89138(6) 0.0425(4) Uani 1 1 d . . . O3 O 0.3950(6) 0.9531(4) 0.8669(2) 0.0710(13) Uani 1 1 d . . . O2 O 0.4519(5) 0.7715(4) 0.9417(2) 0.0720(13) Uani 1 1 d . . . O4 O 0.2156(5) 0.8698(5) 0.9256(2) 0.0854(15) Uani 1 1 d . . . O1 O 0.2845(6) 0.7487(4) 0.8335(2) 0.0770(14) Uani 1 1 d . . . O1W O 0.7604(6) 1.4315(6) 0.5353(4) 0.1028(18) Uani 1 1 d D . . H1W H 0.776(9) 1.493(7) 0.504(4) 0.123 Uiso 1 1 d D . . H2W H 0.843(6) 1.382(7) 0.541(4) 0.123 Uiso 1 1 d D . . O2W O 0.5505(4) 1.2364(4) 0.5387(2) 0.0531(10) Uani 1 1 d D . . H3W H 0.478(4) 1.274(5) 0.556(3) 0.064 Uiso 1 1 d D . . H4W H 0.613(5) 1.305(4) 0.536(3) 0.064 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0131(4) 0.0869(8) 0.0220(4) 0.0146(4) 0.0030(3) -0.0014(4) N1 0.0173(18) 0.050(2) 0.027(2) 0.0064(16) 0.0029(14) 0.0025(17) N2 0.0141(17) 0.056(3) 0.0283(19) 0.0012(17) 0.0055(13) -0.0050(17) N3 0.0179(17) 0.036(2) 0.0285(19) 0.0126(15) 0.0079(14) 0.0016(15) C1 0.029(2) 0.038(3) 0.029(2) 0.0021(18) 0.0057(18) 0.009(2) C2 0.029(2) 0.041(3) 0.022(2) 0.0002(18) 0.0078(17) -0.001(2) C3 0.025(2) 0.044(3) 0.038(3) 0.012(2) 0.0058(18) 0.002(2) C4 0.023(2) 0.049(3) 0.031(2) 0.000(2) 0.0048(17) -0.008(2) C5 0.032(2) 0.034(3) 0.033(2) 0.0019(18) 0.0111(18) -0.003(2) C6 0.020(2) 0.044(3) 0.022(2) 0.0017(18) 0.0097(15) 0.0017(19) C7 0.018(2) 0.039(3) 0.030(2) 0.0049(18) 0.0045(16) -0.0018(18) C8 0.026(2) 0.040(3) 0.028(2) 0.0046(18) 0.0059(17) -0.004(2) C9 0.036(3) 0.036(3) 0.040(3) -0.001(2) 0.010(2) -0.002(2) C10 0.034(3) 0.046(3) 0.038(3) -0.006(2) 0.006(2) -0.001(2) C11 0.035(3) 0.052(3) 0.058(3) -0.010(3) 0.007(2) -0.009(2) C12 0.054(4) 0.081(5) 0.127(7) -0.018(5) -0.037(4) -0.005(4) N4 0.0155(17) 0.053(3) 0.0206(17) 0.0035(16) 0.0025(13) -0.0037(17) Cl1 0.0479(7) 0.0406(8) 0.0383(7) 0.0064(5) 0.0065(5) -0.0003(6) O3 0.096(4) 0.054(3) 0.062(3) 0.005(2) 0.016(2) -0.013(2) O2 0.079(3) 0.072(3) 0.057(3) 0.008(2) -0.006(2) 0.024(2) O4 0.060(3) 0.128(4) 0.076(3) 0.014(3) 0.031(2) 0.012(3) O1 0.096(3) 0.062(3) 0.064(3) -0.009(2) -0.007(2) -0.019(2) O1W 0.067(3) 0.084(4) 0.155(6) 0.019(3) 0.016(3) -0.008(3) O2W 0.037(2) 0.064(3) 0.059(2) -0.0062(19) 0.0110(17) -0.0041(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.022(4) 3_676 ? Cu1 N1 2.022(4) . ? Cu1 N4 2.044(4) 3_576 ? Cu1 N4 2.044(4) 1_655 ? N1 N2 1.312(5) . ? N1 C1 1.366(6) . ? N2 N3 1.309(5) . ? N3 C2 1.336(6) . ? N3 C3 1.457(6) . ? C1 C2 1.336(6) . ? C1 C9 1.501(6) . ? C3 C6 1.518(6) . ? C4 N4 1.347(6) . ? C4 C5 1.378(6) . ? C5 C6 1.368(6) . ? C6 C7 1.379(6) . ? C7 C8 1.357(6) . ? C8 N4 1.350(6) . ? C9 C10 1.509(7) . ? C10 C11 1.507(7) . ? C11 C12 1.505(8) . ? N4 Cu1 2.044(4) 1_455 ? Cl1 O3 1.409(5) . ? Cl1 O4 1.413(5) . ? Cl1 O1 1.415(4) . ? Cl1 O2 1.417(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 179.998(1) 3_676 . ? N1 Cu1 N4 87.97(14) 3_676 3_576 ? N1 Cu1 N4 92.04(14) . 3_576 ? N1 Cu1 N4 92.03(14) 3_676 1_655 ? N1 Cu1 N4 87.96(14) . 1_655 ? N4 Cu1 N4 180.0(2) 3_576 1_655 ? N2 N1 C1 109.7(3) . . ? N2 N1 Cu1 115.9(3) . . ? C1 N1 Cu1 134.5(3) . . ? N3 N2 N1 106.2(3) . . ? N2 N3 C2 111.5(4) . . ? N2 N3 C3 118.9(3) . . ? C2 N3 C3 129.5(4) . . ? C2 C1 N1 106.5(4) . . ? C2 C1 C9 129.1(4) . . ? N1 C1 C9 124.4(4) . . ? C1 C2 N3 106.2(4) . . ? N3 C3 C6 112.1(4) . . ? N4 C4 C5 122.6(4) . . ? C6 C5 C4 118.8(4) . . ? C5 C6 C7 118.5(4) . . ? C5 C6 C3 117.9(4) . . ? C7 C6 C3 123.6(4) . . ? C8 C7 C6 120.4(4) . . ? N4 C8 C7 121.7(4) . . ? C1 C9 C10 113.8(4) . . ? C11 C10 C9 112.4(4) . . ? C12 C11 C10 110.9(5) . . ? C4 N4 C8 117.8(4) . . ? C4 N4 Cu1 120.5(3) . 1_455 ? C8 N4 Cu1 121.7(3) . 1_455 ? O3 Cl1 O4 108.3(3) . . ? O3 Cl1 O1 109.5(3) . . ? O4 Cl1 O1 110.7(3) . . ? O3 Cl1 O2 109.9(3) . . ? O4 Cl1 O2 108.0(3) . . ? O1 Cl1 O2 110.5(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W O4 0.89(2) 2.03(4) 2.872(8) 156(7) 4_685 O1W H1W Cl1 0.89(2) 2.90(2) 3.786(7) 173(8) 4_685 O1W H2W O3 0.88(2) 2.73(8) 3.283(8) 122(7) 2_656 O1W H2W O2 0.88(2) 2.11(2) 2.982(8) 177(9) 2_656 O1W H2W Cl1 0.88(2) 2.93(5) 3.721(6) 150(7) 2_656 O2W H3W O4 0.870(19) 2.06(2) 2.917(6) 168(6) 2_556 O2W H4W O1W 0.892(19) 1.83(2) 2.713(7) 173(5) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.797 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.104 data_b555 _database_code_depnum_ccdc_archive 'CCDC 846707' #TrackingRef 'B555-295K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Cl2 N4 Zn' _chemical_formula_weight 352.56 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' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7644(6) _cell_length_b 15.8088(11) _cell_length_c 11.4395(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.002(2) _cell_angle_gamma 90.00 _cell_volume 1537.90(18) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3286 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 25.88 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 1.936 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5943 _exptl_absorpt_correction_T_max 0.7600 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10670 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3532 _reflns_number_gt 2981 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0540P)^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 3532 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0966 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 1.03093(3) 0.319396(17) 0.78056(2) 0.03642(11) Uani 1 1 d . . . Cl1 Cl 1.03191(8) 0.34383(5) 0.59038(5) 0.05319(18) Uani 1 1 d . . . Cl2 Cl 1.21399(7) 0.38051(4) 0.92394(5) 0.05104(18) Uani 1 1 d . . . N1 N 0.8104(2) 0.34131(12) 0.80508(17) 0.0377(4) Uani 1 1 d . . . N2 N 0.7011(2) 0.37148(12) 0.71387(17) 0.0404(4) Uani 1 1 d . . . N3 N 0.5720(2) 0.37873(12) 0.75572(18) 0.0406(4) Uani 1 1 d . . . N4 N 0.4478(2) 0.69025(12) 0.69947(18) 0.0397(5) Uani 1 1 d . . . C1 C 0.7514(3) 0.33022(14) 0.9037(2) 0.0403(5) Uani 1 1 d . . . C2 C 0.5976(3) 0.35411(15) 0.8710(2) 0.0441(6) Uani 1 1 d . . . H2 H 0.5254 0.3535 0.9187 0.053 Uiso 1 1 calc R . . C3 C 0.8492(3) 0.30236(17) 1.0226(2) 0.0485(6) Uani 1 1 d . . . H3A H 0.9407 0.2722 1.0108 0.058 Uiso 1 1 calc R . . H3B H 0.7889 0.2638 1.0598 0.058 Uiso 1 1 calc R . . C4 C 0.9030(4) 0.37796(18) 1.1066(2) 0.0585(7) Uani 1 1 d . . . H4A H 0.9571 0.4181 1.0668 0.070 Uiso 1 1 calc R . . H4B H 0.8112 0.4060 1.1218 0.070 Uiso 1 1 calc R . . C5 C 1.0110(5) 0.3525(2) 1.2255(3) 0.0710(9) Uani 1 1 d . . . H5A H 1.0976 0.3197 1.2103 0.085 Uiso 1 1 calc R . . H5B H 0.9536 0.3169 1.2691 0.085 Uiso 1 1 calc R . . C6 C 1.0758(6) 0.4283(3) 1.3025(3) 0.0982(13) Uani 1 1 d . . . H6A H 1.1296 0.4647 1.2586 0.147 Uiso 1 1 calc R . . H6B H 1.1479 0.4094 1.3750 0.147 Uiso 1 1 calc R . . H6C H 0.9909 0.4587 1.3228 0.147 Uiso 1 1 calc R . . C7 C 0.4325(3) 0.41911(15) 0.6785(2) 0.0455(6) Uani 1 1 d . . . H7A H 0.3392 0.3992 0.7016 0.055 Uiso 1 1 calc R . . H7B H 0.4238 0.4027 0.5955 0.055 Uiso 1 1 calc R . . C8 C 0.4400(2) 0.51418(15) 0.6881(2) 0.0385(5) Uani 1 1 d . . . C9 C 0.5364(3) 0.55606(17) 0.7834(2) 0.0513(7) Uani 1 1 d . . . H9 H 0.6012 0.5256 0.8455 0.062 Uiso 1 1 calc R . . C10 C 0.5366(3) 0.64259(18) 0.7865(2) 0.0524(7) Uani 1 1 d . . . H10 H 0.6016 0.6696 0.8522 0.063 Uiso 1 1 calc R . . C11 C 0.3533(3) 0.64958(17) 0.6080(2) 0.0495(6) Uani 1 1 d . . . H11 H 0.2890 0.6814 0.5471 0.059 Uiso 1 1 calc R . . C12 C 0.3463(3) 0.56282(16) 0.5993(2) 0.0487(6) Uani 1 1 d . . . H12 H 0.2786 0.5371 0.5337 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02774(16) 0.03979(18) 0.03998(18) 0.00172(10) 0.00479(11) 0.00068(10) Cl1 0.0412(3) 0.0757(5) 0.0417(3) 0.0082(3) 0.0081(3) -0.0004(3) Cl2 0.0374(3) 0.0596(4) 0.0504(4) -0.0088(3) -0.0004(3) -0.0049(3) N1 0.0327(10) 0.0360(10) 0.0440(11) 0.0031(8) 0.0085(8) 0.0000(8) N2 0.0301(10) 0.0411(11) 0.0488(11) 0.0025(9) 0.0072(8) 0.0000(8) N3 0.0282(9) 0.0354(11) 0.0574(12) -0.0010(9) 0.0087(8) -0.0005(8) N4 0.0352(10) 0.0367(11) 0.0426(11) 0.0012(8) 0.0006(8) -0.0017(8) C1 0.0383(13) 0.0333(12) 0.0498(14) 0.0021(10) 0.0113(10) -0.0004(9) C2 0.0390(13) 0.0429(13) 0.0544(15) 0.0032(11) 0.0191(11) 0.0001(11) C3 0.0514(15) 0.0440(14) 0.0526(15) 0.0111(11) 0.0172(12) 0.0046(11) C4 0.073(2) 0.0504(16) 0.0522(15) 0.0029(12) 0.0146(14) 0.0047(14) C5 0.086(2) 0.064(2) 0.0581(18) 0.0073(15) 0.0085(16) -0.0016(18) C6 0.127(3) 0.093(3) 0.070(2) -0.011(2) 0.015(2) -0.031(3) C7 0.0259(11) 0.0410(13) 0.0647(16) -0.0024(12) 0.0011(10) -0.0007(10) C8 0.0255(10) 0.0405(13) 0.0473(12) -0.0038(10) 0.0048(9) -0.0021(9) C9 0.0510(16) 0.0430(15) 0.0479(15) 0.0031(11) -0.0111(12) 0.0026(11) C10 0.0531(16) 0.0461(15) 0.0453(14) -0.0021(11) -0.0129(12) -0.0022(12) C11 0.0415(14) 0.0486(14) 0.0477(14) 0.0031(11) -0.0100(11) 0.0018(11) C12 0.0395(13) 0.0434(14) 0.0515(14) -0.0051(11) -0.0118(10) -0.0027(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N1 2.0490(19) . ? Zn1 N4 2.0578(19) 2_646 ? Zn1 Cl1 2.2116(7) . ? Zn1 Cl2 2.2191(6) . ? N1 N2 1.323(3) . ? N1 C1 1.361(3) . ? N2 N3 1.336(3) . ? N3 C2 1.341(3) . ? N3 C7 1.469(3) . ? N4 C11 1.332(3) . ? N4 C10 1.338(3) . ? N4 Zn1 2.0578(19) 2_656 ? C1 C2 1.362(3) . ? C1 C3 1.488(4) . ? C3 C4 1.535(4) . ? C4 C5 1.511(4) . ? C5 C6 1.513(5) . ? C7 C8 1.507(3) . ? C8 C12 1.376(3) . ? C8 C9 1.376(3) . ? C9 C10 1.368(4) . ? C11 C12 1.375(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N4 102.46(8) . 2_646 ? N1 Zn1 Cl1 109.48(6) . . ? N4 Zn1 Cl1 105.11(6) 2_646 . ? N1 Zn1 Cl2 111.26(6) . . ? N4 Zn1 Cl2 108.66(6) 2_646 . ? Cl1 Zn1 Cl2 118.48(3) . . ? N2 N1 C1 110.63(19) . . ? N2 N1 Zn1 118.69(14) . . ? C1 N1 Zn1 130.68(16) . . ? N1 N2 N3 105.23(18) . . ? N2 N3 C2 111.89(19) . . ? N2 N3 C7 118.4(2) . . ? C2 N3 C7 129.4(2) . . ? C11 N4 C10 116.9(2) . . ? C11 N4 Zn1 126.06(17) . 2_656 ? C10 N4 Zn1 117.09(17) . 2_656 ? N1 C1 C2 106.6(2) . . ? N1 C1 C3 123.0(2) . . ? C2 C1 C3 130.2(2) . . ? N3 C2 C1 105.6(2) . . ? C1 C3 C4 111.3(2) . . ? C5 C4 C3 112.8(2) . . ? C4 C5 C6 112.2(3) . . ? N3 C7 C8 111.98(19) . . ? C12 C8 C9 117.3(2) . . ? C12 C8 C7 119.7(2) . . ? C9 C8 C7 123.0(2) . . ? C10 C9 C8 119.9(2) . . ? N4 C10 C9 123.1(2) . . ? N4 C11 C12 123.1(2) . . ? C11 C12 C8 119.7(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.423 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.073 # Attachment 'B556-100K.cif' data_b556 _database_code_depnum_ccdc_archive 'CCDC 846708' #TrackingRef 'B556-100K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Cl2 N4 Zn' _chemical_formula_weight 352.56 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' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7376(14) _cell_length_b 15.690(3) _cell_length_c 11.0903(17) _cell_angle_alpha 90.00 _cell_angle_beta 102.331(3) _cell_angle_gamma 90.00 _cell_volume 1485.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 965 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.42 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.004 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5847 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10450 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3413 _reflns_number_gt 3174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0330P)^2^+0.5316P] 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 3413 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0265 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0618 _refine_ls_wR_factor_gt 0.0608 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.475740(19) 0.180923(11) 0.722442(16) 0.01435(7) Uani 1 1 d . . . Cl1 Cl 0.47298(4) 0.15511(3) 0.91835(3) 0.01992(9) Uani 1 1 d . . . Cl2 Cl 0.29655(4) 0.11871(3) 0.57619(3) 0.01924(9) Uani 1 1 d . . . N1 N 0.69692(15) 0.16126(8) 0.69614(12) 0.0155(3) Uani 1 1 d . . . N2 N 0.80580(15) 0.13186(8) 0.78860(12) 0.0164(3) Uani 1 1 d . . . N3 N 0.93543(15) 0.12515(8) 0.74380(12) 0.0159(3) Uani 1 1 d . . . N4 N 1.05042(16) -0.18946(8) 0.79729(12) 0.0164(3) Uani 1 1 d . . . C1 C 0.75666(19) 0.17254(10) 0.59296(15) 0.0163(3) Uani 1 1 d . . . C2 C 0.91137(19) 0.14939(10) 0.62447(15) 0.0179(3) Uani 1 1 d . . . H2 H 0.9857 0.1502 0.5733 0.021 Uiso 1 1 calc R . . C3 C 0.65758(19) 0.19862(10) 0.47175(15) 0.0177(3) Uani 1 1 d . . . H3A H 0.7189 0.2364 0.4284 0.021 Uiso 1 1 calc R . . H3B H 0.5659 0.2311 0.4859 0.021 Uiso 1 1 calc R . . C4 C 0.6010(2) 0.12090(10) 0.39064(15) 0.0197(3) Uani 1 1 d . . . H4A H 0.6925 0.0925 0.3686 0.024 Uiso 1 1 calc R . . H4B H 0.5515 0.0798 0.4383 0.024 Uiso 1 1 calc R . . C5 C 0.4840(2) 0.14461(11) 0.27281(16) 0.0225(3) Uani 1 1 d . . . H5A H 0.5367 0.1808 0.2209 0.027 Uiso 1 1 calc R . . H5B H 0.3978 0.1783 0.2944 0.027 Uiso 1 1 calc R . . C6 C 0.4156(2) 0.06640(12) 0.19906(17) 0.0303(4) Uani 1 1 d . . . H6A H 0.4989 0.0361 0.1700 0.046 Uiso 1 1 calc R . . H6B H 0.3347 0.0843 0.1280 0.046 Uiso 1 1 calc R . . H6C H 0.3691 0.0285 0.2517 0.046 Uiso 1 1 calc R . . C7 C 1.07329(18) 0.08419(10) 0.81974(15) 0.0176(3) Uani 1 1 d . . . H7A H 1.0824 0.1010 0.9070 0.021 Uiso 1 1 calc R . . H7B H 1.1684 0.1042 0.7933 0.021 Uiso 1 1 calc R . . C8 C 1.06359(18) -0.01196(10) 0.80949(14) 0.0158(3) Uani 1 1 d . . . C9 C 0.96390(18) -0.05299(11) 0.71334(15) 0.0200(3) Uani 1 1 d . . . H9 H 0.8984 -0.0209 0.6500 0.024 Uiso 1 1 calc R . . C10 C 0.96038(19) -0.14087(11) 0.71014(15) 0.0202(3) Uani 1 1 d . . . H10 H 0.8914 -0.1682 0.6436 0.024 Uiso 1 1 calc R . . C11 C 1.14900(19) -0.14981(11) 0.88953(15) 0.0200(3) Uani 1 1 d . . . H11 H 1.2145 -0.1834 0.9510 0.024 Uiso 1 1 calc R . . C12 C 1.15913(18) -0.06184(11) 0.89879(15) 0.0202(3) Uani 1 1 d . . . H12 H 1.2305 -0.0359 0.9653 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01209(10) 0.01523(11) 0.01504(10) 0.00030(6) 0.00135(7) 0.00047(6) Cl1 0.01707(18) 0.0264(2) 0.01587(19) 0.00194(14) 0.00257(14) 0.00138(15) Cl2 0.01538(17) 0.0222(2) 0.01845(19) -0.00256(14) -0.00018(14) -0.00132(14) N1 0.0132(6) 0.0149(6) 0.0180(6) 0.0010(5) 0.0023(5) 0.0006(5) N2 0.0138(6) 0.0165(6) 0.0182(6) 0.0004(5) 0.0021(5) -0.0003(5) N3 0.0116(6) 0.0150(6) 0.0207(7) -0.0002(5) 0.0025(5) -0.0002(5) N4 0.0156(6) 0.0149(7) 0.0178(6) 0.0003(5) 0.0015(5) 0.0000(5) C1 0.0170(7) 0.0122(7) 0.0195(8) -0.0002(6) 0.0034(6) -0.0014(6) C2 0.0175(7) 0.0162(7) 0.0206(8) 0.0008(6) 0.0055(6) -0.0015(6) C3 0.0190(8) 0.0160(7) 0.0179(7) 0.0034(6) 0.0037(6) 0.0019(6) C4 0.0230(8) 0.0172(8) 0.0192(8) 0.0010(6) 0.0049(6) 0.0007(6) C5 0.0257(8) 0.0200(8) 0.0205(8) 0.0002(6) 0.0022(6) -0.0007(7) C6 0.0377(10) 0.0271(10) 0.0248(9) -0.0025(7) 0.0033(8) -0.0071(8) C7 0.0132(7) 0.0164(8) 0.0214(8) -0.0006(6) -0.0008(6) 0.0002(6) C8 0.0132(7) 0.0166(8) 0.0184(7) -0.0002(6) 0.0049(6) -0.0002(6) C9 0.0189(8) 0.0191(8) 0.0195(8) 0.0019(6) -0.0015(6) 0.0017(6) C10 0.0194(8) 0.0202(8) 0.0180(8) -0.0025(6) -0.0029(6) -0.0011(6) C11 0.0184(8) 0.0192(8) 0.0195(8) 0.0014(6) -0.0023(6) 0.0009(6) C12 0.0172(7) 0.0193(8) 0.0211(8) -0.0015(6) -0.0029(6) -0.0006(6) _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 N1 2.0386(13) . ? Zn1 N4 2.0530(14) 2_656 ? Zn1 Cl1 2.2153(5) . ? Zn1 Cl2 2.2249(5) . ? N1 N2 1.3238(19) . ? N1 C1 1.367(2) . ? N2 N3 1.3346(18) . ? N3 C2 1.350(2) . ? N3 C7 1.463(2) . ? N4 C11 1.341(2) . ? N4 C10 1.345(2) . ? N4 Zn1 2.0530(14) 2_646 ? C1 C2 1.371(2) . ? C1 C3 1.492(2) . ? C3 C4 1.533(2) . ? C4 C5 1.524(2) . ? C5 C6 1.524(2) . ? C7 C8 1.514(2) . ? C8 C9 1.383(2) . ? C8 C12 1.392(2) . ? C9 C10 1.379(2) . ? C11 C12 1.385(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N4 102.83(5) . 2_656 ? N1 Zn1 Cl1 108.78(4) . . ? N4 Zn1 Cl1 105.15(4) 2_656 . ? N1 Zn1 Cl2 111.73(4) . . ? N4 Zn1 Cl2 108.17(4) 2_656 . ? Cl1 Zn1 Cl2 118.777(18) . . ? N2 N1 C1 110.72(13) . . ? N2 N1 Zn1 119.23(10) . . ? C1 N1 Zn1 130.04(11) . . ? N1 N2 N3 105.42(12) . . ? N2 N3 C2 112.08(13) . . ? N2 N3 C7 118.71(13) . . ? C2 N3 C7 128.69(13) . . ? C11 N4 C10 117.83(14) . . ? C11 N4 Zn1 125.42(11) . 2_646 ? C10 N4 Zn1 116.75(11) . 2_646 ? N1 C1 C2 106.52(14) . . ? N1 C1 C3 122.54(14) . . ? C2 C1 C3 130.77(15) . . ? N3 C2 C1 105.26(14) . . ? C1 C3 C4 111.27(13) . . ? C5 C4 C3 112.48(14) . . ? C4 C5 C6 112.23(15) . . ? N3 C7 C8 111.62(13) . . ? C9 C8 C12 118.04(15) . . ? C9 C8 C7 122.52(14) . . ? C12 C8 C7 119.44(14) . . ? C10 C9 C8 119.47(15) . . ? N4 C10 C9 122.79(15) . . ? N4 C11 C12 122.62(15) . . ? C11 C12 C8 119.23(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.402 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.066