# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Chris Adams' _publ_contact_author_address ; Cantock's Close Bristol BS8 1TS ; _publ_contact_author_email ciago@bris.ac.uk loop_ _publ_author_name C.Adams A.Orpen M.Lusi A.Gillon # Attachment '- Combined cifs.cif' data_3(0.86) _database_code_depnum_ccdc_archive 'CCDC 779347' #TrackingRef '- Combined cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl4 Co0.14 N2 Zn0.86' _chemical_formula_weight 364.48 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' 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' Zn Zn 0.2839 1.4301 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.6596(2) _cell_length_b 19.7497(7) _cell_length_c 9.4708(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.067(2) _cell_angle_gamma 90.00 _cell_volume 1354.09(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9783 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 726 _exptl_absorpt_coefficient_mu 2.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.522327 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type ; 'Bruker-Nonius APEX II CCD camera on \k-goniostat' ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 14086 _diffrn_reflns_av_R_equivalents 0.0798 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3096 _reflns_number_gt 2377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement ; DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) Although determined using DirAx, the cell is refined in the HKL package during data reduction ; _computing_data_reduction ; 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' ; _refine_special_details ; Constrained position and thermal eplisoid parameters for Zn1 and Co1. 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^)+(0.0000P)^2^+12.1528P] 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 3096 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1352 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.39839(9) 0.37106(3) 0.29327(7) 0.0175(2) Uani 0.86(3) 1 d P . . Co1 Co 0.39839(9) 0.37106(3) 0.29327(7) 0.0175(2) Uani 0.14(3) 1 d P . . Cl2 Cl 0.3854(2) 0.45092(7) 0.11975(16) 0.0229(3) Uani 1 1 d . . . Cl3 Cl 0.12511(19) 0.36291(7) 0.33453(17) 0.0241(3) Uani 1 1 d . . . Cl4 Cl 0.4720(2) 0.27034(7) 0.20502(17) 0.0249(4) Uani 1 1 d . . . Cl5 Cl 0.62858(19) 0.40380(8) 0.50620(16) 0.0241(4) Uani 1 1 d . . . N1 N 0.7539(7) 0.2968(3) 0.0377(6) 0.0280(12) Uani 1 1 d . . . H1A H 0.6872 0.2765 0.0851 0.034 Uiso 1 1 calc R . . N2 N 1.2809(7) 0.4584(3) -0.3404(6) 0.0247(11) Uani 1 1 d . . . H2A H 1.3490 0.4787 -0.3867 0.030 Uiso 1 1 calc R . . C8 C 1.0720(7) 0.3949(3) -0.1931(6) 0.0186(12) Uani 1 1 d . . . C6 C 1.3161(8) 0.3936(3) -0.2992(7) 0.0250(13) Uani 1 1 d . . . H6A H 1.4119 0.3701 -0.3219 0.030 Uiso 1 1 calc R . . C3 C 0.9611(8) 0.3598(3) -0.1120(6) 0.0189(12) Uani 1 1 d . . . C9 C 1.0369(8) 0.4620(3) -0.2419(7) 0.0218(12) Uani 1 1 d . . . H9A H 0.9378 0.4861 -0.2257 0.026 Uiso 1 1 calc R . . C1 C 0.8750(9) 0.2608(3) -0.0039(7) 0.0289(14) Uani 1 1 d . . . H1B H 0.8879 0.2137 0.0173 0.035 Uiso 1 1 calc R . . C10 C 1.1456(9) 0.4931(3) -0.3134(7) 0.0270(14) Uani 1 1 d . . . H10A H 1.1244 0.5391 -0.3434 0.032 Uiso 1 1 calc R . . C2 C 0.9829(8) 0.2915(3) -0.0782(7) 0.0254(13) Uani 1 1 d . . . H2B H 1.0713 0.2657 -0.1059 0.030 Uiso 1 1 calc R . . C7 C 1.2149(8) 0.3612(3) -0.2249(7) 0.0238(13) Uani 1 1 d . . . H7A H 1.2420 0.3154 -0.1945 0.029 Uiso 1 1 calc R . . C4 C 0.8328(9) 0.3955(3) -0.0653(7) 0.0282(14) Uani 1 1 d . . . H4A H 0.8160 0.4426 -0.0854 0.034 Uiso 1 1 calc R . . C5 C 0.7306(9) 0.3632(4) 0.0095(7) 0.0341(16) Uani 1 1 d . . . H5A H 0.6435 0.3879 0.0411 0.041 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 0.0175(4) 0.0157(4) 0.0184(4) -0.0004(3) 0.0048(3) -0.0011(3) Co1 0.0175(4) 0.0157(4) 0.0184(4) -0.0004(3) 0.0048(3) -0.0011(3) Cl2 0.0282(7) 0.0177(7) 0.0206(7) 0.0030(5) 0.0049(6) 0.0007(6) Cl3 0.0178(7) 0.0259(8) 0.0289(8) -0.0018(6) 0.0078(6) -0.0028(6) Cl4 0.0290(8) 0.0167(7) 0.0338(8) -0.0007(6) 0.0167(6) 0.0002(6) Cl5 0.0217(7) 0.0298(8) 0.0192(7) 0.0014(6) 0.0044(6) -0.0065(6) N1 0.020(3) 0.041(3) 0.025(3) 0.004(2) 0.010(2) -0.007(2) N2 0.026(3) 0.024(3) 0.023(3) 0.001(2) 0.008(2) -0.007(2) C8 0.017(3) 0.021(3) 0.016(3) -0.006(2) 0.002(2) 0.000(2) C6 0.023(3) 0.021(3) 0.033(3) -0.005(3) 0.013(3) -0.003(2) C3 0.019(3) 0.020(3) 0.016(3) -0.002(2) 0.004(2) 0.001(2) C9 0.021(3) 0.016(3) 0.026(3) -0.002(2) 0.005(2) 0.001(2) C1 0.032(3) 0.024(3) 0.032(4) 0.006(3) 0.013(3) 0.000(3) C10 0.032(3) 0.021(3) 0.026(3) 0.002(2) 0.006(3) -0.005(3) C2 0.025(3) 0.022(3) 0.032(3) 0.003(3) 0.013(3) 0.005(3) C7 0.028(3) 0.018(3) 0.029(3) -0.003(2) 0.015(3) 0.001(2) C4 0.033(3) 0.020(3) 0.038(4) 0.006(3) 0.020(3) 0.008(3) C5 0.030(3) 0.051(5) 0.025(3) 0.003(3) 0.015(3) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 Cl2 2.2564(15) . ? Zn1 Cl3 2.2570(15) . ? Zn1 Cl5 2.2958(15) . ? Zn1 Cl4 2.2980(15) . ? N1 C1 1.327(8) . ? N1 C5 1.338(9) . ? N1 H1A 0.8800 . ? N2 C10 1.335(8) . ? N2 C6 1.340(8) . ? N2 H2A 0.8800 . ? C8 C7 1.395(8) . ? C8 C9 1.401(8) . ? C8 C3 1.490(8) . ? C6 C7 1.365(8) . ? C6 H6A 0.9500 . ? C3 C2 1.385(8) . ? C3 C4 1.393(8) . ? C9 C10 1.378(8) . ? C9 H9A 0.9500 . ? C1 C2 1.387(8) . ? C1 H1B 0.9500 . ? C10 H10A 0.9500 . ? C2 H2B 0.9500 . ? C7 H7A 0.9500 . ? C4 C5 1.373(9) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Zn1 Cl3 110.68(6) . . ? Cl2 Zn1 Cl5 106.34(6) . . ? Cl3 Zn1 Cl5 110.95(6) . . ? Cl2 Zn1 Cl4 107.33(6) . . ? Cl3 Zn1 Cl4 110.67(6) . . ? Cl5 Zn1 Cl4 110.73(6) . . ? C1 N1 C5 121.8(6) . . ? C1 N1 H1A 119.1 . . ? C5 N1 H1A 119.1 . . ? C10 N2 C6 122.0(5) . . ? C10 N2 H2A 119.0 . . ? C6 N2 H2A 119.0 . . ? C7 C8 C9 117.4(5) . . ? C7 C8 C3 120.7(5) . . ? C9 C8 C3 121.9(5) . . ? N2 C6 C7 120.3(6) . . ? N2 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C2 C3 C4 117.6(6) . . ? C2 C3 C8 121.7(5) . . ? C4 C3 C8 120.6(5) . . ? C10 C9 C8 120.1(6) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? N1 C1 C2 120.4(6) . . ? N1 C1 H1B 119.8 . . ? C2 C1 H1B 119.8 . . ? N2 C10 C9 119.8(6) . . ? N2 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C3 C2 C1 119.7(6) . . ? C3 C2 H2B 120.1 . . ? C1 C2 H2B 120.1 . . ? C6 C7 C8 120.3(6) . . ? C6 C7 H7A 119.8 . . ? C8 C7 H7A 119.8 . . ? C5 C4 C3 120.6(6) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? N1 C5 C4 119.8(6) . . ? N1 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N2 C6 C7 -1.2(9) . . . . ? C7 C8 C3 C2 -6.4(8) . . . . ? C9 C8 C3 C2 172.9(6) . . . . ? C7 C8 C3 C4 172.6(6) . . . . ? C9 C8 C3 C4 -8.1(8) . . . . ? C7 C8 C9 C10 -2.3(8) . . . . ? C3 C8 C9 C10 178.4(5) . . . . ? C5 N1 C1 C2 0.3(10) . . . . ? C6 N2 C10 C9 -0.4(9) . . . . ? C8 C9 C10 N2 2.2(9) . . . . ? C4 C3 C2 C1 1.7(9) . . . . ? C8 C3 C2 C1 -179.3(6) . . . . ? N1 C1 C2 C3 -1.4(10) . . . . ? N2 C6 C7 C8 1.0(9) . . . . ? C9 C8 C7 C6 0.7(9) . . . . ? C3 C8 C7 C6 -180.0(5) . . . . ? C2 C3 C4 C5 -0.9(9) . . . . ? C8 C3 C4 C5 180.0(6) . . . . ? C1 N1 C5 C4 0.4(10) . . . . ? C3 C4 C5 N1 -0.1(10) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.713 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.164 #===END data_3(0.95) _database_code_depnum_ccdc_archive 'CCDC 779348' #TrackingRef '- Combined cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl4 Co0.05 N2 Zn0.95' _chemical_formula_weight 364.90 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' Co Co 0.3494 0.9721 '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 'P 21/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 7.6491(6) _cell_length_b 19.7209(16) _cell_length_c 9.4569(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.049(2) _cell_angle_gamma 90.00 _cell_volume 1348.43(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 983 _cell_measurement_theta_min 4.85 _cell_measurement_theta_max 29.45 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 727 _exptl_absorpt_coefficient_mu 2.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9508 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6893 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 12415 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 29.48 _reflns_number_total 3745 _reflns_number_gt 3604 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+0.4005P] 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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3745 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0228 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0580 _refine_ls_wR_factor_gt 0.0575 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.601567(17) 0.628935(6) 0.706635(14) 0.01628(6) Uani 0.953(8) 1 d P . . Co1 Co 0.601567(17) 0.628935(6) 0.706635(14) 0.01628(6) Uani 0.047(8) 1 d P . . Cl2 Cl 0.61421(4) 0.549106(13) 0.88009(3) 0.02129(7) Uani 1 1 d . . . Cl3 Cl 0.87478(4) 0.636995(14) 0.66546(3) 0.02229(8) Uani 1 1 d . . . Cl4 Cl 0.52807(4) 0.729619(13) 0.79443(3) 0.02270(8) Uani 1 1 d . . . Cl5 Cl 0.37125(4) 0.596094(15) 0.49372(3) 0.02178(7) Uani 1 1 d . . . N1 N -0.24593(14) 0.29662(6) 1.03724(12) 0.0266(2) Uani 1 1 d . . . H1A H -0.3134 0.2762 1.0841 0.032 Uiso 1 1 calc R . . N2 N 0.28041(14) 0.45822(5) 0.65934(11) 0.0227(2) Uani 1 1 d . . . H2A H 0.3481 0.4788 0.6128 0.027 Uiso 1 1 calc R . . C8 C 0.07130(14) 0.39472(6) 0.80630(12) 0.01662(19) Uani 1 1 d . . . C6 C 0.31714(17) 0.39363(7) 0.69977(14) 0.0245(2) Uani 1 1 d . . . H6A H 0.4136 0.3704 0.6772 0.029 Uiso 1 1 calc R . . C3 C -0.03860(15) 0.36015(6) 0.88862(12) 0.01722(19) Uani 1 1 d . . . C9 C 0.03623(16) 0.46208(6) 0.75892(13) 0.0211(2) Uani 1 1 d . . . H9A H -0.0620 0.4863 0.7765 0.025 Uiso 1 1 calc R . . C1 C -0.12391(19) 0.26022(7) 0.99576(16) 0.0285(3) Uani 1 1 d . . . H1B H -0.1107 0.2131 1.0170 0.034 Uiso 1 1 calc R . . C10 C 0.14448(17) 0.49312(6) 0.68676(14) 0.0237(2) Uani 1 1 d . . . H10A H 0.1229 0.5391 0.6565 0.028 Uiso 1 1 calc R . . C2 C -0.01687(17) 0.29114(6) 0.92195(15) 0.0242(2) Uani 1 1 d . . . H2B H 0.0716 0.2655 0.8938 0.029 Uiso 1 1 calc R . . C7 C 0.21407(17) 0.36067(6) 0.77471(14) 0.0219(2) Uani 1 1 d . . . H7A H 0.2405 0.3148 0.8047 0.026 Uiso 1 1 calc R . . C4 C -0.16707(19) 0.39603(7) 0.93516(16) 0.0287(3) Uani 1 1 d . . . H4A H -0.1844 0.4432 0.9153 0.034 Uiso 1 1 calc R . . C5 C -0.2690(2) 0.36274(8) 1.01014(17) 0.0312(3) Uani 1 1 d . . . H5A H -0.3561 0.3872 1.0425 0.037 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 0.01579(8) 0.01505(8) 0.01848(8) -0.00029(4) 0.00624(5) -0.00071(4) Co1 0.01579(8) 0.01505(8) 0.01848(8) -0.00029(4) 0.00624(5) -0.00071(4) Cl2 0.02543(14) 0.01631(12) 0.02070(13) 0.00254(8) 0.00554(10) 0.00105(9) Cl3 0.01656(13) 0.02327(13) 0.02832(15) -0.00162(10) 0.00906(10) -0.00193(9) Cl4 0.02691(14) 0.01530(12) 0.03189(15) -0.00060(9) 0.01779(11) -0.00079(9) Cl5 0.01839(12) 0.02813(14) 0.01854(13) 0.00020(9) 0.00565(9) -0.00588(9) N1 0.0202(4) 0.0399(6) 0.0214(5) 0.0016(4) 0.0091(4) -0.0068(4) N2 0.0233(5) 0.0249(5) 0.0215(4) -0.0008(4) 0.0096(4) -0.0078(4) C8 0.0166(4) 0.0170(5) 0.0163(4) -0.0014(3) 0.0054(4) -0.0006(4) C6 0.0248(5) 0.0263(6) 0.0271(6) -0.0019(4) 0.0150(5) -0.0010(4) C3 0.0164(4) 0.0185(5) 0.0178(5) -0.0004(4) 0.0070(4) 0.0006(4) C9 0.0200(5) 0.0182(5) 0.0245(5) 0.0008(4) 0.0067(4) 0.0004(4) C1 0.0301(6) 0.0250(6) 0.0335(6) 0.0031(5) 0.0146(5) -0.0050(5) C10 0.0244(5) 0.0189(5) 0.0261(5) 0.0021(4) 0.0061(4) -0.0036(4) C2 0.0250(5) 0.0192(5) 0.0327(6) 0.0023(4) 0.0153(5) 0.0011(4) C7 0.0247(5) 0.0191(5) 0.0269(5) 0.0008(4) 0.0151(5) 0.0023(4) C4 0.0318(6) 0.0273(6) 0.0339(6) 0.0049(5) 0.0204(5) 0.0097(5) C5 0.0269(6) 0.0423(7) 0.0301(6) 0.0035(5) 0.0173(5) 0.0074(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 Zn1 Cl2 2.2527(3) . ? Zn1 Cl3 2.2528(3) . ? Zn1 Cl4 2.2919(3) . ? Zn1 Cl5 2.2939(3) . ? N1 C5 1.3294(19) . ? N1 C1 1.3339(18) . ? N1 H1A 0.8800 . ? N2 C6 1.3331(17) . ? N2 C10 1.3409(17) . ? N2 H2A 0.8800 . ? C8 C7 1.3950(15) . ? C8 C9 1.3996(15) . ? C8 C3 1.4848(15) . ? C6 C7 1.3824(16) . ? C6 H6A 0.9500 . ? C3 C4 1.3937(16) . ? C3 C2 1.3946(16) . ? C9 C10 1.3765(17) . ? C9 H9A 0.9500 . ? C1 C2 1.3793(17) . ? C1 H1B 0.9500 . ? C10 H10A 0.9500 . ? C2 H2B 0.9500 . ? C7 H7A 0.9500 . ? C4 C5 1.3793(19) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Zn1 Cl3 110.693(12) . . ? Cl2 Zn1 Cl4 107.396(12) . . ? Cl3 Zn1 Cl4 110.642(11) . . ? Cl2 Zn1 Cl5 106.260(12) . . ? Cl3 Zn1 Cl5 110.990(13) . . ? Cl4 Zn1 Cl5 110.713(12) . . ? C5 N1 C1 122.19(11) . . ? C5 N1 H1A 118.9 . . ? C1 N1 H1A 118.9 . . ? C6 N2 C10 122.62(11) . . ? C6 N2 H2A 118.7 . . ? C10 N2 H2A 118.7 . . ? C7 C8 C9 118.03(10) . . ? C7 C8 C3 120.53(10) . . ? C9 C8 C3 121.43(10) . . ? N2 C6 C7 119.62(11) . . ? N2 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C4 C3 C2 117.92(11) . . ? C4 C3 C8 120.71(11) . . ? C2 C3 C8 121.37(10) . . ? C10 C9 C8 119.82(11) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? N1 C1 C2 119.92(12) . . ? N1 C1 H1B 120.0 . . ? C2 C1 H1B 120.0 . . ? N2 C10 C9 119.83(11) . . ? N2 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C1 C2 C3 119.95(11) . . ? C1 C2 H2B 120.0 . . ? C3 C2 H2B 120.0 . . ? C6 C7 C8 120.05(11) . . ? C6 C7 H7A 120.0 . . ? C8 C7 H7A 120.0 . . ? C5 C4 C3 119.73(12) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? N1 C5 C4 120.27(12) . . ? N1 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N2 C6 C7 -0.83(19) . . . . ? C7 C8 C3 C4 172.73(12) . . . . ? C9 C8 C3 C4 -6.90(17) . . . . ? C7 C8 C3 C2 -7.21(17) . . . . ? C9 C8 C3 C2 173.16(11) . . . . ? C7 C8 C9 C10 -1.56(17) . . . . ? C3 C8 C9 C10 178.08(11) . . . . ? C5 N1 C1 C2 -0.1(2) . . . . ? C6 N2 C10 C9 -0.22(18) . . . . ? C8 C9 C10 N2 1.44(18) . . . . ? N1 C1 C2 C3 -1.1(2) . . . . ? C4 C3 C2 C1 1.46(19) . . . . ? C8 C3 C2 C1 -178.61(11) . . . . ? N2 C6 C7 C8 0.66(19) . . . . ? C9 C8 C7 C6 0.52(18) . . . . ? C3 C8 C7 C6 -179.12(11) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? C8 C3 C4 C5 179.34(12) . . . . ? C1 N1 C5 C4 0.9(2) . . . . ? C3 C4 C5 N1 -0.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 29.48 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.406 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.054 #===END data_3(0.93) _database_code_depnum_ccdc_archive 'CCDC 779349' #TrackingRef '- Combined cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl4 Co0.07 N2 Zn0.93' _chemical_formula_weight 364.90 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' 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' Zn Zn 0.2839 1.4301 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.65960(10) _cell_length_b 19.7388(4) _cell_length_c 9.4616(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.0620(10) _cell_angle_gamma 90.00 _cell_volume 1352.07(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9605 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.793 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 727 _exptl_absorpt_coefficient_mu 2.544 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6253 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17759 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3100 _reflns_number_gt 2837 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement ; DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction ; _computing_data_reduction ; DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0174P)^2^+0.7961P] 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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3100 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0216 _refine_ls_wR_factor_ref 0.0503 _refine_ls_wR_factor_gt 0.0489 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.39839(2) 0.371069(9) 0.29334(2) 0.01333(8) Uani 0.928(10) 1 d P . . Co1 Co 0.39839(2) 0.371069(9) 0.29334(2) 0.01333(8) Uani 0.072(10) 1 d P . . Cl2 Cl 0.38579(6) 0.45092(2) 0.11988(4) 0.01867(10) Uani 1 1 d . . . Cl3 Cl 0.12520(6) 0.36304(2) 0.33455(5) 0.01966(10) Uani 1 1 d . . . Cl4 Cl 0.47188(6) 0.27038(2) 0.20549(5) 0.02009(10) Uani 1 1 d . . . Cl5 Cl 0.62870(5) 0.40391(2) 0.50626(4) 0.01910(10) Uani 1 1 d . . . N1 N 0.7540(2) 0.29672(8) 0.03702(16) 0.0237(3) Uani 1 1 d . . . H1A H 0.6867 0.2763 0.0839 0.028 Uiso 1 1 calc R . . N2 N 1.2803(2) 0.45814(7) -0.34043(15) 0.0198(3) Uani 1 1 d . . . H2A H 1.3480 0.4787 -0.3868 0.024 Uiso 1 1 calc R . . C8 C 1.0715(2) 0.39491(8) -0.19375(17) 0.0136(3) Uani 1 1 d . . . C6 C 1.3168(3) 0.39374(9) -0.3002(2) 0.0221(4) Uani 1 1 d . . . H6A H 1.4133 0.3706 -0.3226 0.026 Uiso 1 1 calc R . . C3 C 0.9612(2) 0.36014(8) -0.11132(17) 0.0147(3) Uani 1 1 d . . . C9 C 1.0364(2) 0.46196(9) -0.24101(19) 0.0180(3) Uani 1 1 d . . . H9A H 0.9382 0.4861 -0.2234 0.022 Uiso 1 1 calc R . . C1 C 0.8761(3) 0.26048(10) -0.0045(2) 0.0256(4) Uani 1 1 d . . . H1B H 0.8894 0.2134 0.0167 0.031 Uiso 1 1 calc R . . C10 C 1.1444(2) 0.49300(9) -0.31317(19) 0.0209(4) Uani 1 1 d . . . H10A H 1.1227 0.5390 -0.3436 0.025 Uiso 1 1 calc R . . C2 C 0.9825(2) 0.29129(9) -0.0781(2) 0.0215(4) Uani 1 1 d . . . H2B H 1.0707 0.2656 -0.1064 0.026 Uiso 1 1 calc R . . C7 C 1.2138(2) 0.36073(9) -0.2257(2) 0.0195(4) Uani 1 1 d . . . H7A H 1.2398 0.3148 -0.1962 0.023 Uiso 1 1 calc R . . C4 C 0.8330(3) 0.39582(10) -0.0647(2) 0.0257(4) Uani 1 1 d . . . H4A H 0.8160 0.4430 -0.0844 0.031 Uiso 1 1 calc R . . C5 C 0.7308(3) 0.36288(10) 0.0098(2) 0.0278(4) Uani 1 1 d . . . H5A H 0.6437 0.3873 0.0418 0.033 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 0.01304(12) 0.01187(11) 0.01516(11) -0.00025(7) 0.00471(8) -0.00069(7) Co1 0.01304(12) 0.01187(11) 0.01516(11) -0.00025(7) 0.00471(8) -0.00069(7) Cl2 0.0231(2) 0.0136(2) 0.01736(19) 0.00284(14) 0.00403(16) 0.00133(15) Cl3 0.0142(2) 0.0205(2) 0.0253(2) -0.00180(16) 0.00791(16) -0.00192(15) Cl4 0.0245(2) 0.0124(2) 0.0288(2) -0.00054(15) 0.01620(18) -0.00064(16) Cl5 0.0160(2) 0.0252(2) 0.01546(19) 0.00009(15) 0.00426(15) -0.00598(16) N1 0.0166(7) 0.0378(9) 0.0177(7) 0.0022(6) 0.0070(6) -0.0079(7) N2 0.0202(7) 0.0225(8) 0.0182(7) -0.0001(6) 0.0083(6) -0.0081(6) C8 0.0138(8) 0.0146(8) 0.0117(7) -0.0022(6) 0.0032(6) -0.0013(6) C6 0.0228(9) 0.0240(9) 0.0234(9) -0.0021(7) 0.0131(7) -0.0005(7) C3 0.0130(8) 0.0168(8) 0.0134(7) -0.0009(6) 0.0032(6) 0.0003(6) C9 0.0167(8) 0.0151(8) 0.0212(8) -0.0003(6) 0.0049(7) 0.0011(7) C1 0.0272(10) 0.0205(9) 0.0303(10) 0.0020(7) 0.0112(8) -0.0045(7) C10 0.0223(9) 0.0157(8) 0.0221(8) 0.0019(7) 0.0036(7) -0.0039(7) C2 0.0226(9) 0.0167(8) 0.0291(9) 0.0008(7) 0.0135(7) 0.0003(7) C7 0.0227(9) 0.0160(8) 0.0232(9) 0.0000(7) 0.0122(7) 0.0011(7) C4 0.0284(10) 0.0249(10) 0.0292(10) 0.0045(8) 0.0166(8) 0.0090(8) C5 0.0233(10) 0.0389(12) 0.0262(10) 0.0034(8) 0.0150(8) 0.0082(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 Cl2 2.2547(4) . ? Zn1 Cl3 2.2559(4) . ? Zn1 Cl4 2.2943(4) . ? Zn1 Cl5 2.2955(4) . ? N1 C5 1.332(3) . ? N1 C1 1.334(2) . ? N1 H1A 0.8800 . ? N2 C6 1.330(2) . ? N2 C10 1.341(2) . ? N2 H2A 0.8800 . ? C8 C9 1.395(2) . ? C8 C7 1.397(2) . ? C8 C3 1.491(2) . ? C6 C7 1.381(2) . ? C6 H6A 0.9500 . ? C3 C2 1.392(2) . ? C3 C4 1.393(2) . ? C9 C10 1.377(2) . ? C9 H9A 0.9500 . ? C1 C2 1.375(2) . ? C1 H1B 0.9500 . ? C10 H10A 0.9500 . ? C2 H2B 0.9500 . ? C7 H7A 0.9500 . ? C4 C5 1.375(3) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Zn1 Cl3 110.691(17) . . ? Cl2 Zn1 Cl4 107.404(16) . . ? Cl3 Zn1 Cl4 110.669(16) . . ? Cl2 Zn1 Cl5 106.222(16) . . ? Cl3 Zn1 Cl5 111.009(16) . . ? Cl4 Zn1 Cl5 110.696(17) . . ? C5 N1 C1 122.04(16) . . ? C5 N1 H1A 119.0 . . ? C1 N1 H1A 119.0 . . ? C6 N2 C10 122.62(15) . . ? C6 N2 H2A 118.7 . . ? C10 N2 H2A 118.7 . . ? C9 C8 C7 118.13(15) . . ? C9 C8 C3 121.45(15) . . ? C7 C8 C3 120.42(15) . . ? N2 C6 C7 119.69(16) . . ? N2 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C2 C3 C4 117.70(16) . . ? C2 C3 C8 121.52(15) . . ? C4 C3 C8 120.78(15) . . ? C10 C9 C8 119.82(16) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? N1 C1 C2 120.05(17) . . ? N1 C1 H1B 120.0 . . ? C2 C1 H1B 120.0 . . ? N2 C10 C9 119.80(16) . . ? N2 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C1 C2 C3 120.05(17) . . ? C1 C2 H2B 120.0 . . ? C3 C2 H2B 120.0 . . ? C6 C7 C8 119.92(16) . . ? C6 C7 H7A 120.0 . . ? C8 C7 H7A 120.0 . . ? C5 C4 C3 120.10(18) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? N1 C5 C4 120.05(17) . . ? N1 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N2 C6 C7 -0.8(3) . . . . ? C9 C8 C3 C2 173.01(16) . . . . ? C7 C8 C3 C2 -7.0(2) . . . . ? C9 C8 C3 C4 -7.0(2) . . . . ? C7 C8 C3 C4 172.93(16) . . . . ? C7 C8 C9 C10 -1.8(2) . . . . ? C3 C8 C9 C10 178.19(15) . . . . ? C5 N1 C1 C2 -0.1(3) . . . . ? C6 N2 C10 C9 -0.1(3) . . . . ? C8 C9 C10 N2 1.4(3) . . . . ? N1 C1 C2 C3 -0.9(3) . . . . ? C4 C3 C2 C1 1.3(3) . . . . ? C8 C3 C2 C1 -178.70(16) . . . . ? N2 C6 C7 C8 0.4(3) . . . . ? C9 C8 C7 C6 0.9(2) . . . . ? C3 C8 C7 C6 -179.05(16) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C8 C3 C4 C5 179.26(17) . . . . ? C1 N1 C5 C4 0.7(3) . . . . ? C3 C4 C5 N1 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.313 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.070