# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email gaosong@pku.edu.cn _publ_contact_author_name 'Song Gao' loop_ _publ_author_name 'Song Gao' 'Den-Feng Weng' 'Bing-Wu Wang' 'Zheming Wang' data_1 _database_code_depnum_ccdc_archive 'CCDC 802430' #TrackingRef 'CuClmela.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 Cl6 Cu N12' _chemical_formula_weight 532.55 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' 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 'P 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.6942(2) _cell_length_b 5.7300(1) _cell_length_c 15.4546(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.4383(9) _cell_angle_gamma 90.00 _cell_volume 898.41(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7206 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.969 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 534 _exptl_absorpt_coefficient_mu 2.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.502 _exptl_absorpt_correction_T_max 0.606 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _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 'NONIUS KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 13212 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2067 _reflns_number_gt 1537 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _publ_section_references ; collect: "Collect" data collection software, Nonius B.V., Delft, The Netherlands, 1998. HKL Scalepack & HKL Denzo: Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press. absorption correction: R.H. Blessing (1995) Acta Cryst. A51, 33-37. R.H. Blessing (1997) J.Appl. Cryst. 30, 421-426. maXus: S.Mackay, C.J.Gilmore, C.Edwards, M. Tremayne, N. Stuart, K.Shankland "maXus: a computer program for the solution and refinement of crystal structures from diffraction data", University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan (1998). Sheldrick, G. M. (1998). SHELXTL Version 5.1. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1997). SHELX-97. PC Version. University of Goettingen, Germany. ; _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^)+(0.0387P)^2^+0.2295P] 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 SHELXL _refine_ls_extinction_coef 0.0233(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2067 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 Cu1 Cu 0.0000 0.98881(7) 0.2500 0.02848(14) Uani 1 2 d S . . Cl1 Cl 0.0000 0.51187(15) 0.2500 0.0384(2) Uani 1 2 d S . . Cl2 Cl 0.06396(5) 0.99358(9) 0.40829(4) 0.02955(15) Uani 1 1 d . . . Cl3 Cl 0.22097(5) 1.00162(9) 0.25610(4) 0.03019(16) Uani 1 1 d . . . Cl4 Cl 0.5000 0.41624(16) 0.2500 0.0348(2) Uani 1 2 d S . . C1 C 0.3124(2) 0.4415(4) 0.44747(15) 0.0241(5) Uani 1 1 d . . . C2 C 0.2037(2) 0.4566(4) 0.55837(15) 0.0248(5) Uani 1 1 d . . . C3 C 0.35984(19) 0.1681(4) 0.55868(14) 0.0254(5) Uani 1 1 d . . . N1 N 0.22480(17) 0.5439(3) 0.48402(13) 0.0266(4) Uani 1 1 d . . . H1 H 0.1826 0.6666 0.4587 0.032 Uiso 1 1 calc R . . N2 N 0.26904(16) 0.2616(3) 0.59396(12) 0.0251(4) Uani 1 1 d . . . H2 H 0.2536 0.1949 0.6394 0.030 Uiso 1 1 calc R . . N3 N 0.38337(15) 0.2559(3) 0.48609(12) 0.0254(4) Uani 1 1 d . . . N4 N 0.32613(18) 0.5374(3) 0.37429(13) 0.0323(5) Uani 1 1 d . . . H4A H 0.3818 0.4809 0.3501 0.039 Uiso 1 1 calc R . . H4B H 0.2795 0.6571 0.3503 0.039 Uiso 1 1 calc R . . N5 N 0.12214(19) 0.5573(4) 0.59393(14) 0.0356(5) Uani 1 1 d . . . H5A H 0.0810 0.6818 0.5695 0.043 Uiso 1 1 calc R . . H5B H 0.1095 0.4993 0.6418 0.043 Uiso 1 1 calc R . . N6 N 0.4253(2) -0.0171(3) 0.59937(15) 0.0386(5) Uani 1 1 d . . . H6A H 0.4831 -0.0806 0.5788 0.046 Uiso 1 1 calc R . . H6B H 0.4102 -0.0746 0.6465 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 Cu1 0.0246(2) 0.0424(3) 0.0197(2) 0.000 0.00866(16) 0.000 Cl1 0.0352(5) 0.0515(6) 0.0327(5) 0.000 0.0169(4) 0.000 Cl2 0.0351(3) 0.0302(3) 0.0230(3) 0.0010(2) 0.0085(2) 0.0060(2) Cl3 0.0315(3) 0.0316(3) 0.0293(3) -0.0012(2) 0.0120(2) 0.0007(2) Cl4 0.0389(5) 0.0373(5) 0.0340(5) 0.000 0.0196(4) 0.000 C1 0.0226(11) 0.0267(12) 0.0227(12) -0.0011(9) 0.0068(9) -0.0002(8) C2 0.0261(11) 0.0251(13) 0.0228(12) -0.0034(9) 0.0070(9) -0.0016(9) C3 0.0255(11) 0.0245(12) 0.0238(11) 0.0005(9) 0.0042(9) 0.0018(9) N1 0.0290(10) 0.0254(11) 0.0279(11) 0.0058(8) 0.0124(8) 0.0085(7) N2 0.0296(10) 0.0284(11) 0.0191(9) 0.0018(8) 0.0102(8) 0.0009(7) N3 0.0256(9) 0.0270(10) 0.0243(10) 0.0046(8) 0.0088(8) 0.0063(7) N4 0.0335(11) 0.0393(12) 0.0285(11) 0.0110(9) 0.0159(9) 0.0119(8) N5 0.0399(11) 0.0418(13) 0.0320(12) 0.0015(9) 0.0211(10) 0.0087(9) N6 0.0428(12) 0.0388(13) 0.0377(13) 0.0134(10) 0.0177(10) 0.0141(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 Cl2 2.3226(5) . ? Cu1 Cl2 2.3226(5) 2 ? Cu1 Cl3 2.3361(5) 2 ? Cu1 Cl3 2.3361(5) . ? Cu1 Cl1 2.7329(10) . ? Cu1 Cl1 2.9971(10) . 1565 C1 N4 1.307(3) . ? C1 N3 1.333(3) . ? C1 N1 1.370(3) . ? C2 N5 1.304(3) . ? C2 N1 1.336(3) . ? C2 N2 1.340(3) . ? C3 N6 1.316(3) . ? C3 N3 1.324(3) . ? C3 N2 1.365(3) . ? N1 H1 0.8600 . ? N2 H2 0.8600 . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? 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 Cu1 Cl2 178.65(3) . 2 ? Cl2 Cu1 Cl3 89.96(2) . 2 ? Cl2 Cu1 Cl3 90.00(2) 2 2 ? Cl2 Cu1 Cl3 90.00(2) . . ? Cl2 Cu1 Cl3 89.96(2) 2 . ? Cl3 Cu1 Cl3 176.40(3) 2 . ? Cl2 Cu1 Cl1 90.675(16) . . ? Cl2 Cu1 Cl1 90.675(16) 2 . ? Cl3 Cu1 Cl1 91.800(16) 2 . ? Cl3 Cu1 Cl1 91.800(16) . . ? Cl2 Cu1 Cl1 89.33(2) . 1_565 ? Cl3 Cu1 Cl1 88.20(2) . 1_565 ? Cl2 Cu1 Cl1 89.33(2) 2_555 1_565 ? Cl3 Cu1 Cl1 88.20(2) 2_555 1_565 ? Cl1 Cu1 Cl1 180.00(0) . 1_565 ? N4 C1 N3 121.28(19) . . ? N4 C1 N1 117.09(19) . . ? N3 C1 N1 121.60(19) . . ? N5 C2 N1 120.9(2) . . ? N5 C2 N2 121.8(2) . . ? N1 C2 N2 117.21(19) . . ? N6 C3 N3 119.8(2) . . ? N6 C3 N2 117.6(2) . . ? N3 C3 N2 122.62(19) . . ? C2 N1 C1 121.18(18) . . ? C2 N1 H1 119.4 . . ? C1 N1 H1 119.4 . . ? C2 N2 C3 120.52(19) . . ? C2 N2 H2 119.7 . . ? C3 N2 H2 119.7 . . ? C3 N3 C1 116.67(18) . . ? C1 N4 H4A 120.0 . . ? C1 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C2 N5 H5A 120.0 . . ? C2 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C3 N6 H6A 120.0 . . ? C3 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? 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 N1 H1 Cl2 0.86 2.26 3.1136(18) 172.7 . N2 H2 Cl3 0.86 2.25 3.1037(18) 175.9 4_566 N4 H4A Cl4 0.86 2.32 3.1445(18) 161.7 . N4 H4B Cl3 0.86 2.41 3.2212(19) 156.4 . N5 H5A Cl2 0.86 2.51 3.247(2) 143.7 3_576 N5 H5B Cl1 0.86 2.33 3.1103(19) 151.8 3_566 N6 H6A N3 0.86 2.23 3.084(3) 174.5 3_656 N6 H6B Cl4 0.86 2.52 3.180(2) 134.4 3_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.527 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.072 #===END OF 1 data_2 _database_code_depnum_ccdc_archive 'CCDC 802431' #TrackingRef 'CuClmela.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H16 Cl6 Cu N12' _chemical_formula_sum 'C6 H16 Cl6 Cu N12' _chemical_formula_weight 532.55 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' 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 'P 21/m' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.68570(10) _cell_length_b 15.0893(4) _cell_length_c 10.3687(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.8634(8) _cell_angle_gamma 90.00 _cell_volume 888.45(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8432 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.991 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 534 _exptl_absorpt_coefficient_mu 2.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.740 _exptl_absorpt_correction_T_max 0.906 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _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 'NONIUS KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 15831 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2118 _reflns_number_gt 1544 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0412P)^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 SHELXL _refine_ls_extinction_coef 0.0019(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2118 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Cu1 Cu 0.52259(7) 0.2500 -0.11003(4) 0.02906(15) Uani 1 2 d S . . Cl1 Cl 1.00667(16) 0.2500 -0.09445(9) 0.0424(3) Uani 1 2 d S . . Cl2 Cl 0.51518(9) 0.40608(4) -0.10379(6) 0.03257(17) Uani 1 1 d . . . Cl3 Cl 0.51384(13) 0.2500 -0.32954(8) 0.0314(2) Uani 1 2 d S . . Cl4 Cl 0.52340(14) 0.2500 0.11692(8) 0.0285(2) Uani 1 2 d S . . Cl5 Cl 0.10465(14) 0.2500 0.36349(8) 0.0306(2) Uani 1 2 d S . . C1 C 0.9401(4) 0.56125(15) 0.3439(2) 0.0232(5) Uani 1 1 d . . . C2 C 0.9763(4) 0.45042(15) 0.1851(2) 0.0243(5) Uani 1 1 d . . . C3 C 0.6822(3) 0.44650(14) 0.3364(2) 0.0231(5) Uani 1 1 d . . . N1 N 1.0496(3) 0.52644(12) 0.24077(18) 0.0246(4) Uani 1 1 d . . . H1 H 1.1679 0.5539 0.2111 0.029 Uiso 1 1 calc R . . N2 N 0.7851(3) 0.41216(12) 0.23188(17) 0.0241(4) Uani 1 1 d . . . H2 H 0.7271 0.3653 0.1953 0.029 Uiso 1 1 calc R . . N3 N 0.7591(3) 0.52020(12) 0.39519(17) 0.0230(4) Uani 1 1 d . . . N4 N 1.0248(3) 0.63493(13) 0.39230(18) 0.0306(5) Uani 1 1 d . . . H4A H 0.9639 0.6581 0.4587 0.037 Uiso 1 1 calc R . . H4B H 1.1416 0.6604 0.3579 0.037 Uiso 1 1 calc R . . N5 N 1.0866(3) 0.41512(13) 0.09013(18) 0.0318(5) Uani 1 1 d . . . H5A H 1.2092 0.4407 0.0620 0.038 Uiso 1 1 calc R . . H5B H 1.0366 0.3663 0.0558 0.038 Uiso 1 1 calc R . . N6 N 0.5008(3) 0.40354(14) 0.37973(18) 0.0339(5) Uani 1 1 d . . . H6A H 0.4318 0.4231 0.4460 0.041 Uiso 1 1 calc R . . H6B H 0.4512 0.3559 0.3417 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 Cu1 0.0421(3) 0.0237(2) 0.0217(2) 0.000 0.00499(18) 0.000 Cl1 0.0626(6) 0.0339(5) 0.0305(5) 0.000 -0.0003(4) 0.000 Cl2 0.0300(3) 0.0340(4) 0.0346(4) 0.0053(3) 0.0105(3) -0.0001(2) Cl3 0.0272(4) 0.0422(5) 0.0250(5) 0.000 0.0025(3) 0.000 Cl4 0.0360(4) 0.0252(4) 0.0241(5) 0.000 0.0011(3) 0.000 Cl5 0.0347(4) 0.0314(5) 0.0259(5) 0.000 0.0042(3) 0.000 C1 0.0230(11) 0.0238(12) 0.0225(12) 0.0020(10) 0.0002(10) 0.0019(9) C2 0.0272(11) 0.0215(12) 0.0242(13) 0.0015(10) 0.0003(10) 0.0039(9) C3 0.0227(11) 0.0238(12) 0.0229(12) 0.0027(10) 0.0030(9) 0.0011(9) N1 0.0232(9) 0.0258(11) 0.0257(11) -0.0019(9) 0.0106(8) -0.0047(8) N2 0.0271(10) 0.0190(10) 0.0264(11) -0.0039(8) 0.0043(8) -0.0018(8) N3 0.0226(9) 0.0241(11) 0.0230(10) -0.0006(8) 0.0067(8) -0.0035(8) N4 0.0364(11) 0.0274(11) 0.0293(12) -0.0055(9) 0.0131(9) -0.0101(9) N5 0.0357(11) 0.0295(12) 0.0315(12) -0.0061(9) 0.0130(9) -0.0008(9) N6 0.0339(11) 0.0326(12) 0.0364(13) -0.0101(10) 0.0140(9) -0.0109(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 Cl3 2.2741(9) . ? Cu1 Cl4 2.3530(9) . ? Cu1 Cl2 2.3564(6) 4_565 ? Cu1 Cl2 2.3564(6) . ? Cu1 Cl1 2.7490(10) . ? Cu1 Cl1 2.9457(16) 1_455 ? C1 N4 1.302(3) . ? C1 N3 1.334(3) . ? C1 N1 1.369(3) . ? C2 N5 1.307(3) . ? C2 N1 1.341(3) . ? C2 N2 1.343(3) . ? C3 N6 1.316(3) . ? C3 N3 1.331(3) . ? C3 N2 1.360(3) . ? N1 H1 0.8600 . ? N2 H2 0.8600 . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? 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 Cl3 Cu1 Cl4 178.86(3) . . ? Cl3 Cu1 Cl2 91.603(17) . 4_565 ? Cl4 Cu1 Cl2 88.376(17) . 4_565 ? Cl3 Cu1 Cl2 91.604(17) . . ? Cl4 Cu1 Cl2 88.376(17) . . ? Cl2 Cu1 Cl2 176.16(3) 4_565 . ? Cl3 Cu1 Cl1 91.75(3) . . ? Cl4 Cu1 Cl1 89.39(3) . . ? Cl2 Cu1 Cl1 91.010(15) 4_565 . ? Cl2 Cu1 Cl1 91.010(15) . . ? Cl1 Cu1 Cl1 173.51(6) . 1_455 ? Cl2 Cu1 Cl1 88.82(2) . 1_455 ? Cl2 Cu1 Cl1 88.82(2) 4_655 1_455 ? Cl3 Cu1 Cl1 94.74(4) . 1_455 ? Cl4 Cu1 Cl1 84.13(4) . 1_455 ? N4 C1 N3 121.4(2) . . ? N4 C1 N1 117.0(2) . . ? N3 C1 N1 121.5(2) . . ? N5 C2 N1 121.5(2) . . ? N5 C2 N2 121.7(2) . . ? N1 C2 N2 116.9(2) . . ? N6 C3 N3 120.0(2) . . ? N6 C3 N2 117.4(2) . . ? N3 C3 N2 122.55(19) . . ? C2 N1 C1 121.39(19) . . ? C2 N1 H1 119.3 . . ? C1 N1 H1 119.3 . . ? C2 N2 C3 120.86(19) . . ? C2 N2 H2 119.6 . . ? C3 N2 H2 119.6 . . ? C3 N3 C1 116.61(19) . . ? C1 N4 H4A 120.0 . . ? C1 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C2 N5 H5A 120.0 . . ? C2 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C3 N6 H6A 120.0 . . ? C3 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? 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 N1 H1 Cl2 0.86 2.25 3.0867(17) 165.4 3_765 N2 H2 Cl4 0.86 2.22 3.0734(18) 170.6 . N4 H4A Cl5 0.86 2.35 3.187(2) 162.8 3_666 N4 H4B Cl3 0.86 2.41 3.2388(19) 161.9 3_765 N5 H5A Cl2 0.86 2.56 3.2386(19) 136.5 1_655 N5 H5A Cl2 0.86 2.81 3.520(2) 140.4 3_765 N5 H5B Cl1 0.86 2.35 3.161(2) 157.9 . N6 H6A N3 0.86 2.19 3.049(3) 175.6 3_666 N6 H6B Cl5 0.86 2.56 3.2297(19) 135.9 . N6 H6B Cl4 0.86 2.87 3.584(2) 141.2 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.481 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.078