# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Prof. Chun-Hua Yan' _publ_contact_author_email bais@imre.a-star.edu.sg loop_ _publ_author_name 'Chunhua Yan' 'Shi-Qiang Bai' 'Chen-Jie Fang' 'En-Qing Gao' 'Zheng He' data_1 _database_code_depnum_ccdc_archive 'CCDC 295719' #TrackingRef '- DT-ART-06-2012-031186-Rev-CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Mn2 N16' _chemical_formula_weight 516.30 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' Mn Mn 0.3368 0.7283 '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 10.3381(5) _cell_length_b 12.6101(5) _cell_length_c 8.2479(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.1167(13) _cell_angle_gamma 90.00 _cell_volume 1038.03(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7634 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description flake _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 1.257 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.912 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details '(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 0.76 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 17240 _diffrn_reflns_av_R_equivalents 0.1127 _diffrn_reflns_av_sigmaI/netI 0.1121 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2372 _reflns_number_gt 1203 _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)' _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^)+(0.0210P)^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 0.0045(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2372 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0517 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.856 _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 Mn1 Mn 0.12901(4) 0.56364(3) 0.14439(4) 0.04041(15) Uani 1 1 d . . . N1 N 0.3339(2) 0.48944(15) 0.2505(2) 0.0440(5) Uani 1 1 d . . . N2 N 0.1155(2) 0.46192(15) 0.3702(2) 0.0447(5) Uani 1 1 d . . . N3 N -0.0848(2) 0.57860(16) 0.0325(2) 0.0485(5) Uani 1 1 d . . . N4 N -0.1677(2) 0.61425(18) 0.0936(2) 0.0516(6) Uani 1 1 d . . . N5 N -0.2492(3) 0.6476(2) 0.1527(3) 0.0888(9) Uani 1 1 d . . . N6 N 0.2080(2) 0.64633(18) -0.0431(3) 0.0634(7) Uani 1 1 d . . . N7 N 0.1727(2) 0.72048(18) -0.1271(2) 0.0460(5) Uani 1 1 d . . . N8 N 0.1401(3) 0.79258(19) -0.2116(3) 0.0902(9) Uani 1 1 d . . . C1 C 0.4423(3) 0.5029(2) 0.1948(3) 0.0566(7) Uani 1 1 d . . . H1 H 0.4419 0.5567 0.1175 0.068 Uiso 1 1 calc R . . C2 C 0.5559(3) 0.4405(3) 0.2464(3) 0.0686(8) Uani 1 1 d . . . H2 H 0.6299 0.4521 0.2044 0.082 Uiso 1 1 calc R . . C3 C 0.5571(3) 0.3615(3) 0.3604(3) 0.0723(9) Uani 1 1 d . . . H3 H 0.6315 0.3177 0.3959 0.087 Uiso 1 1 calc R . . C4 C 0.4470(3) 0.3479(2) 0.4216(3) 0.0627(8) Uani 1 1 d . . . H4 H 0.4464 0.2953 0.5006 0.075 Uiso 1 1 calc R . . C5 C 0.3374(3) 0.41260(19) 0.3650(3) 0.0479(7) Uani 1 1 d . . . C6 C 0.2168(3) 0.4032(2) 0.4269(3) 0.0536(8) Uani 1 1 d . . . H6 H 0.2148 0.3533 0.5092 0.064 Uiso 1 1 calc R . . C7 C 0.0023(2) 0.45189(19) 0.4450(3) 0.0502(7) Uani 1 1 d . . . H7A H 0.0119 0.3878 0.5121 0.060 Uiso 1 1 calc R . . H7B H -0.0807 0.4470 0.3570 0.060 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 Mn1 0.0428(3) 0.0396(2) 0.0390(2) -0.00069(19) 0.01081(16) 0.0001(2) N1 0.0405(15) 0.0544(14) 0.0375(11) 0.0013(10) 0.0107(10) 0.0027(11) N2 0.0475(15) 0.0491(14) 0.0399(10) -0.0040(9) 0.0158(10) 0.0004(11) N3 0.0414(14) 0.0497(14) 0.0543(12) -0.0107(11) 0.0120(11) 0.0070(11) N4 0.0513(17) 0.0494(15) 0.0521(13) -0.0008(11) 0.0097(12) 0.0039(12) N5 0.080(2) 0.104(2) 0.0920(19) -0.0057(17) 0.0396(17) 0.0293(17) N6 0.0641(18) 0.0585(16) 0.0706(15) 0.0269(13) 0.0230(13) 0.0105(13) N7 0.0494(15) 0.0467(15) 0.0430(12) -0.0020(11) 0.0142(11) -0.0040(12) N8 0.121(3) 0.0587(17) 0.0874(18) 0.0358(15) 0.0202(17) 0.0123(17) C1 0.050(2) 0.074(2) 0.0461(14) 0.0035(14) 0.0125(14) 0.0060(17) C2 0.047(2) 0.100(2) 0.0587(17) -0.0068(18) 0.0131(15) 0.007(2) C3 0.048(2) 0.088(3) 0.073(2) -0.0054(18) 0.0014(17) 0.0230(18) C4 0.062(2) 0.062(2) 0.0600(17) 0.0067(14) 0.0079(16) 0.0128(17) C5 0.050(2) 0.0497(18) 0.0431(13) 0.0008(12) 0.0112(13) 0.0071(14) C6 0.067(2) 0.0542(19) 0.0417(14) 0.0038(12) 0.0189(14) 0.0012(16) C7 0.0541(18) 0.0571(18) 0.0453(13) -0.0031(11) 0.0234(13) -0.0048(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 Mn1 N8 2.154(2) 4_576 ? Mn1 N3 2.170(2) . ? Mn1 N6 2.192(2) . ? Mn1 N1 2.2721(19) . ? Mn1 N3 2.2818(19) 3_565 ? Mn1 N2 2.2955(18) . ? N1 C1 1.329(3) . ? N1 C5 1.347(3) . ? N2 C6 1.268(3) . ? N2 C7 1.464(3) . ? N3 N4 1.190(3) . ? N3 Mn1 2.2818(19) 3_565 ? N4 N5 1.157(3) . ? N6 N7 1.164(3) . ? N7 N8 1.142(3) . ? N8 Mn1 2.154(2) 4_575 ? C1 C2 1.385(3) . ? C2 C3 1.368(4) . ? C3 C4 1.371(4) . ? C4 C5 1.376(3) . ? C5 C6 1.470(3) . ? C7 C7 1.523(4) 3_566 ? 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 N8 Mn1 N3 93.63(9) 4_576 . ? N8 Mn1 N6 90.71(9) 4_576 . ? N3 Mn1 N6 100.62(8) . . ? N8 Mn1 N1 102.94(9) 4_576 . ? N3 Mn1 N1 160.67(7) . . ? N6 Mn1 N1 89.20(8) . . ? N8 Mn1 N3 170.81(9) 4_576 3_565 ? N3 Mn1 N3 77.55(8) . 3_565 ? N6 Mn1 N3 88.41(8) . 3_565 ? N1 Mn1 N3 86.20(7) . 3_565 ? N8 Mn1 N2 91.65(8) 4_576 . ? N3 Mn1 N2 97.06(8) . . ? N6 Mn1 N2 161.97(8) . . ? N1 Mn1 N2 72.85(7) . . ? N3 Mn1 N2 92.02(7) 3_565 . ? C1 N1 C5 117.6(2) . . ? C1 N1 Mn1 126.88(17) . . ? C5 N1 Mn1 114.70(17) . . ? C6 N2 C7 117.9(2) . . ? C6 N2 Mn1 113.97(17) . . ? C7 N2 Mn1 127.91(16) . . ? N4 N3 Mn1 128.26(16) . . ? N4 N3 Mn1 121.42(18) . 3_565 ? Mn1 N3 Mn1 102.45(8) . 3_565 ? N5 N4 N3 179.1(3) . . ? N7 N6 Mn1 133.23(19) . . ? N8 N7 N6 178.4(3) . . ? N7 N8 Mn1 166.3(2) . 4_575 ? N1 C1 C2 123.0(3) . . ? C3 C2 C1 118.7(3) . . ? C2 C3 C4 119.0(3) . . ? C3 C4 C5 119.4(3) . . ? N1 C5 C4 122.2(2) . . ? N1 C5 C6 115.6(2) . . ? C4 C5 C6 122.2(2) . . ? N2 C6 C5 121.2(2) . . ? N2 C7 C7 109.5(2) . 3_566 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.247 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.050 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 671838' #TrackingRef '- DT-ART-06-2012-031186-Rev-CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cl N7 Ni O4' _chemical_formula_weight 440.50 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' Ni Ni 0.3393 1.1124 '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 12.4066(11) _cell_length_b 19.6819(12) _cell_length_c 8.0216(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.102(2) _cell_angle_gamma 90.00 _cell_volume 1861.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22341 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.017 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.222 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details '(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 0.76 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 27270 _diffrn_reflns_av_R_equivalents 0.2919 _diffrn_reflns_av_sigmaI/netI 0.2699 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3268 _reflns_number_gt 1117 _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)' _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^)+(0.0213P)^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 0.0010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3268 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2377 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0642 _refine_ls_goodness_of_fit_ref 0.820 _refine_ls_restrained_S_all 0.820 _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 Ni1 Ni 0.27160(7) 0.34492(4) 0.80394(9) 0.0539(3) Uani 1 1 d . . . N1 N 0.4242(4) 0.3447(3) 1.0030(6) 0.0594(13) Uani 1 1 d . . . N2 N 0.2215(5) 0.3811(2) 1.0113(7) 0.0625(14) Uani 1 1 d . . . N3 N 0.1160(4) 0.3500(3) 0.6128(5) 0.0576(14) Uani 1 1 d . . . N4 N 0.2779(5) 0.4412(3) 0.7088(7) 0.0725(17) Uani 1 1 d . . . N5 N 0.3484(4) 0.3135(2) 0.6165(6) 0.0686(16) Uani 1 1 d . . . N6 N 0.2951(4) 0.2839(2) 0.4895(7) 0.0538(14) Uani 1 1 d . . . N7 N 0.2417(4) 0.2562(2) 0.3586(5) 0.0661(16) Uani 1 1 d . . . C1 C 0.5221(6) 0.3216(3) 0.9988(8) 0.068(2) Uani 1 1 d . . . H1 H 0.5306 0.3113 0.8904 0.082 Uiso 1 1 calc R . . C2 C 0.6139(6) 0.3118(3) 1.1480(10) 0.084(2) Uani 1 1 d . . . H2 H 0.6816 0.2938 1.1408 0.101 Uiso 1 1 calc R . . C3 C 0.6020(7) 0.3291(4) 1.3041(9) 0.089(2) Uani 1 1 d . . . H3 H 0.6630 0.3239 1.4058 0.107 Uiso 1 1 calc R . . C4 C 0.5011(6) 0.3545(3) 1.3151(8) 0.078(2) Uani 1 1 d . . . H4 H 0.4923 0.3669 1.4220 0.093 Uiso 1 1 calc R . . C5 C 0.4139(6) 0.3604(3) 1.1605(8) 0.0596(18) Uani 1 1 d . . . C6 C 0.3019(7) 0.3840(3) 1.1545(8) 0.075(2) Uani 1 1 d . . . H6 H 0.2892 0.4010 1.2549 0.089 Uiso 1 1 calc R . . C7 C 0.1075(6) 0.4020(3) 0.9998(7) 0.093(2) Uani 1 1 d . . . H7A H 0.0565 0.3644 0.9612 0.139 Uiso 1 1 calc R . . H7B H 0.0846 0.4387 0.9175 0.139 Uiso 1 1 calc R . . H7C H 0.1059 0.4168 1.1130 0.139 Uiso 1 1 calc R . . C8 C 0.0381(6) 0.3014(4) 0.5660(8) 0.074(2) Uani 1 1 d . . . H8 H 0.0492 0.2616 0.6316 0.089 Uiso 1 1 calc R . . C9 C -0.0601(6) 0.3076(5) 0.4219(10) 0.099(3) Uani 1 1 d . . . H9 H -0.1133 0.2728 0.3905 0.119 Uiso 1 1 calc R . . C10 C -0.0743(8) 0.3671(5) 0.3295(10) 0.105(3) Uani 1 1 d . . . H10 H -0.1388 0.3730 0.2335 0.126 Uiso 1 1 calc R . . C11 C 0.0045(8) 0.4180(4) 0.3753(10) 0.093(3) Uani 1 1 d . . . H11 H -0.0053 0.4584 0.3120 0.112 Uiso 1 1 calc R . . C12 C 0.0997(7) 0.4073(5) 0.5198(9) 0.069(2) Uani 1 1 d . . . C13 C 0.1915(8) 0.4564(3) 0.5798(9) 0.077(2) Uani 1 1 d . . . H13 H 0.1871 0.4983 0.5245 0.093 Uiso 1 1 calc R . . C14 C 0.3718(5) 0.4895(3) 0.7667(8) 0.111(3) Uani 1 1 d . . . H14A H 0.3491 0.5324 0.7098 0.167 Uiso 1 1 calc R . . H14B H 0.4360 0.4724 0.7370 0.167 Uiso 1 1 calc R . . H14C H 0.3920 0.4954 0.8915 0.167 Uiso 1 1 calc R . . Cl1 Cl 0.2402(2) 0.59381(13) 1.2002(3) 0.0993(7) Uani 1 1 d . . . O1 O 0.3381(6) 0.5686(5) 1.2988(9) 0.268(5) Uani 1 1 d . . . O2 O 0.2395(7) 0.6605(3) 1.1711(10) 0.245(4) Uani 1 1 d . . . O3 O 0.2142(7) 0.5653(3) 1.0437(7) 0.245(4) Uani 1 1 d . . . O4 O 0.1627(6) 0.5779(4) 1.2788(10) 0.256(4) 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 Ni1 0.0571(5) 0.0558(5) 0.0462(4) 0.0009(5) 0.0122(3) -0.0009(6) N1 0.062(4) 0.062(4) 0.053(3) -0.009(3) 0.015(3) -0.002(4) N2 0.069(4) 0.057(4) 0.069(4) -0.003(3) 0.033(3) 0.002(3) N3 0.047(4) 0.066(4) 0.054(3) 0.004(4) 0.009(3) 0.003(4) N4 0.087(5) 0.056(4) 0.080(4) 0.007(3) 0.033(4) 0.000(4) N5 0.066(4) 0.080(4) 0.054(3) -0.010(3) 0.011(3) -0.008(3) N6 0.048(4) 0.054(4) 0.060(4) 0.010(3) 0.019(3) 0.008(3) N7 0.068(4) 0.061(4) 0.058(3) -0.003(3) 0.003(3) 0.007(3) C1 0.069(5) 0.075(6) 0.054(4) -0.006(4) 0.009(4) 0.002(4) C2 0.066(6) 0.092(6) 0.081(5) -0.005(4) 0.003(5) -0.004(4) C3 0.077(6) 0.095(7) 0.076(5) 0.009(5) -0.004(5) -0.019(5) C4 0.081(5) 0.082(6) 0.063(4) 0.001(4) 0.011(4) -0.034(5) C5 0.053(5) 0.058(5) 0.063(5) -0.002(4) 0.011(4) -0.011(4) C6 0.100(6) 0.072(5) 0.051(4) -0.003(4) 0.024(4) -0.016(5) C7 0.086(6) 0.110(6) 0.093(5) 0.000(4) 0.044(4) 0.018(5) C8 0.053(5) 0.096(6) 0.062(4) 0.011(4) 0.003(4) 0.003(5) C9 0.055(6) 0.140(9) 0.096(6) -0.010(5) 0.016(5) -0.004(5) C10 0.077(7) 0.154(11) 0.079(6) 0.019(6) 0.016(5) 0.034(7) C11 0.096(7) 0.116(8) 0.076(6) 0.030(5) 0.039(5) 0.033(6) C12 0.073(6) 0.083(7) 0.053(5) 0.011(5) 0.019(4) 0.027(5) C13 0.109(7) 0.050(5) 0.085(6) 0.019(4) 0.048(5) 0.024(5) C14 0.112(6) 0.082(6) 0.141(6) 0.003(5) 0.040(5) -0.036(5) Cl1 0.0971(17) 0.120(2) 0.0723(12) 0.0072(15) 0.0142(12) -0.0045(17) O1 0.146(6) 0.406(13) 0.185(7) -0.006(6) -0.046(5) 0.071(7) O2 0.376(11) 0.061(4) 0.361(9) 0.023(6) 0.208(8) -0.003(7) O3 0.415(12) 0.198(7) 0.084(4) -0.019(5) 0.022(6) -0.025(7) O4 0.173(7) 0.383(12) 0.256(8) 0.168(7) 0.130(6) 0.060(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 Ni1 N4 2.054(5) . ? Ni1 N3 2.061(4) . ? Ni1 N1 2.063(4) . ? Ni1 N2 2.074(4) . ? Ni1 N7 2.097(5) 4_566 ? Ni1 N5 2.107(5) . ? N1 C1 1.307(6) . ? N1 C5 1.345(6) . ? N2 C6 1.268(6) . ? N2 C7 1.448(6) . ? N3 C8 1.329(7) . ? N3 C12 1.334(7) . ? N4 C13 1.272(6) . ? N4 C14 1.463(6) . ? N5 N6 1.182(5) . ? N6 N7 1.185(5) . ? N7 Ni1 2.097(5) 4_565 ? C1 C2 1.386(7) . ? C2 C3 1.349(7) . ? C3 C4 1.376(8) . ? C4 C5 1.374(7) . ? C5 C6 1.451(7) . ? C8 C9 1.400(7) . ? C9 C10 1.367(8) . ? C10 C11 1.369(9) . ? C11 C12 1.390(8) . ? C12 C13 1.456(8) . ? Cl1 O3 1.320(5) . ? Cl1 O1 1.323(6) . ? Cl1 O2 1.332(6) . ? Cl1 O4 1.340(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 N4 Ni1 N3 79.3(2) . . ? N4 Ni1 N1 99.1(2) . . ? N3 Ni1 N1 176.5(2) . . ? N4 Ni1 N2 92.13(19) . . ? N3 Ni1 N2 97.8(2) . . ? N1 Ni1 N2 79.1(2) . . ? N4 Ni1 N7 169.7(2) . 4_566 ? N3 Ni1 N7 90.9(2) . 4_566 ? N1 Ni1 N7 90.91(18) . 4_566 ? N2 Ni1 N7 92.37(17) . 4_566 ? N4 Ni1 N5 85.86(19) . . ? N3 Ni1 N5 90.56(17) . . ? N1 Ni1 N5 92.4(2) . . ? N2 Ni1 N5 170.9(2) . . ? N7 Ni1 N5 91.1(2) 4_566 . ? C1 N1 C5 117.7(5) . . ? C1 N1 Ni1 128.1(4) . . ? C5 N1 Ni1 113.2(4) . . ? C6 N2 C7 121.5(6) . . ? C6 N2 Ni1 113.2(4) . . ? C7 N2 Ni1 125.2(4) . . ? C8 N3 C12 118.7(6) . . ? C8 N3 Ni1 127.4(5) . . ? C12 N3 Ni1 113.6(5) . . ? C13 N4 C14 119.5(6) . . ? C13 N4 Ni1 113.5(5) . . ? C14 N4 Ni1 126.9(4) . . ? N6 N5 Ni1 120.3(4) . . ? N5 N6 N7 177.6(6) . . ? N6 N7 Ni1 122.3(4) . 4_565 ? N1 C1 C2 123.2(6) . . ? C3 C2 C1 117.9(7) . . ? C2 C3 C4 121.1(7) . . ? C5 C4 C3 116.7(6) . . ? N1 C5 C4 123.4(6) . . ? N1 C5 C6 114.3(6) . . ? C4 C5 C6 122.3(7) . . ? N2 C6 C5 119.5(6) . . ? N3 C8 C9 122.7(7) . . ? C10 C9 C8 117.1(8) . . ? C9 C10 C11 121.4(9) . . ? C10 C11 C12 117.7(8) . . ? N3 C12 C11 122.4(8) . . ? N3 C12 C13 114.2(7) . . ? C11 C12 C13 123.4(9) . . ? N4 C13 C12 119.2(7) . . ? O3 Cl1 O1 108.5(5) . . ? O3 Cl1 O2 105.4(4) . . ? O1 Cl1 O2 115.3(6) . . ? O3 Cl1 O4 110.4(6) . . ? O1 Cl1 O4 107.0(5) . . ? O2 Cl1 O4 110.2(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.291 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.068 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 671839' #TrackingRef '- DT-ART-06-2012-031186-Rev-CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 Cu N9' _chemical_formula_weight 330.81 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5342(2) _cell_length_b 19.6392(4) _cell_length_c 7.01900(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.9956(7) _cell_angle_gamma 90.00 _cell_volume 1309.27(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24391 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description prime _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 1.677 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.816 _exptl_absorpt_correction_T_max 0.946 _exptl_absorpt_process_details '(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 0.76 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 26544 _diffrn_reflns_av_R_equivalents 0.0941 _diffrn_reflns_av_sigmaI/netI 0.0779 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2984 _reflns_number_gt 1715 _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)' _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^)+(0.0424P)^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 0.0016(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2984 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _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 0.01656(3) 0.726702(16) 0.71715(4) 0.03897(13) Uani 1 1 d . . . N1 N -0.1293(2) 0.65537(11) 0.6328(3) 0.0384(5) Uani 1 1 d . . . N2 N 0.1309(2) 0.64034(10) 0.7868(3) 0.0350(5) Uani 1 1 d . . . C10 C 0.4688(4) 0.58537(19) 1.0356(5) 0.0705(10) Uani 1 1 d . . . H10 H 0.5083 0.5500 1.1103 0.085 Uiso 1 1 calc R . . N4 N 0.1219(2) 0.71847(11) 0.4134(3) 0.0401(5) Uani 1 1 d . . . N5 N 0.1973(2) 0.67045(12) 0.3908(3) 0.0410(5) Uani 1 1 d . . . N6 N 0.2722(3) 0.62497(14) 0.3803(4) 0.0644(7) Uani 1 1 d . . . N7 N -0.0977(2) 0.80032(12) 0.5998(3) 0.0497(6) Uani 1 1 d . . . N8 N -0.0827(2) 0.85954(12) 0.6346(3) 0.0429(6) Uani 1 1 d . . . N9 N -0.0739(3) 0.91716(12) 0.6595(4) 0.0646(7) Uani 1 1 d . . . C1 C -0.2590(3) 0.66455(15) 0.5538(4) 0.0501(7) Uani 1 1 d . . . H1 H -0.2903 0.7087 0.5273 0.060 Uiso 1 1 calc R . . C2 C -0.3502(3) 0.61064(17) 0.5091(4) 0.0610(9) Uani 1 1 d . . . H2 H -0.4409 0.6186 0.4537 0.073 Uiso 1 1 calc R . . C3 C -0.3048(3) 0.54568(17) 0.5478(4) 0.0614(9) Uani 1 1 d . . . H3 H -0.3640 0.5088 0.5186 0.074 Uiso 1 1 calc R . . C4 C -0.1697(3) 0.53556(14) 0.6308(4) 0.0507(7) Uani 1 1 d . . . H4 H -0.1362 0.4919 0.6594 0.061 Uiso 1 1 calc R . . C5 C -0.0863(3) 0.59151(13) 0.6698(4) 0.0382(6) Uani 1 1 d . . . C6 C 0.0607(3) 0.58590(13) 0.7521(3) 0.0401(7) Uani 1 1 d . . . H6 H 0.1014 0.5435 0.7782 0.048 Uiso 1 1 calc R . . C7 C 0.2758(3) 0.63714(14) 0.8580(4) 0.0410(7) Uani 1 1 d . . . C8 C 0.3308(3) 0.58438(15) 0.9724(4) 0.0576(8) Uani 1 1 d . . . H8 H 0.2734 0.5487 1.0054 0.069 Uiso 1 1 calc R . . C9 C 0.3637(3) 0.68946(15) 0.8140(4) 0.0480(7) Uani 1 1 d . . . H9 H 0.3263 0.7247 0.7368 0.058 Uiso 1 1 calc R . . N3 N 0.5012(3) 0.69206(17) 0.8776(4) 0.0780(8) Uani 1 1 d . . . C11 C 0.5484(4) 0.6387(3) 0.9885(6) 0.0858(12) Uani 1 1 d . . . H11 H 0.6426 0.6388 1.0355 0.103 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 0.0370(2) 0.03095(18) 0.0474(2) -0.00161(16) -0.00519(14) 0.00122(16) N1 0.0306(13) 0.0404(13) 0.0436(12) -0.0020(10) -0.0006(10) -0.0025(10) N2 0.0349(13) 0.0339(12) 0.0361(11) -0.0006(9) 0.0016(10) -0.0019(10) C10 0.057(2) 0.079(3) 0.069(2) 0.0010(19) -0.0251(19) 0.029(2) N4 0.0433(14) 0.0366(13) 0.0403(12) 0.0019(10) 0.0033(10) 0.0074(11) N5 0.0436(15) 0.0422(14) 0.0363(12) -0.0014(10) -0.0017(11) -0.0033(13) N6 0.0664(19) 0.0552(17) 0.0710(17) -0.0083(14) 0.0033(14) 0.0201(15) N7 0.0479(16) 0.0329(13) 0.0653(16) -0.0013(11) -0.0130(12) 0.0073(12) N8 0.0372(14) 0.0456(16) 0.0451(13) 0.0043(11) -0.0016(11) 0.0076(12) N9 0.074(2) 0.0368(16) 0.0810(18) -0.0063(13) -0.0036(15) 0.0040(14) C1 0.0395(18) 0.0511(19) 0.0590(18) -0.0018(14) 0.0008(15) 0.0021(15) C2 0.0346(18) 0.073(2) 0.073(2) -0.0100(18) -0.0084(16) -0.0054(17) C3 0.049(2) 0.053(2) 0.081(2) -0.0078(17) -0.0017(18) -0.0158(16) C4 0.049(2) 0.0421(17) 0.0597(18) 0.0003(14) -0.0007(15) -0.0074(14) C5 0.0376(16) 0.0356(15) 0.0412(15) -0.0021(12) 0.0018(12) -0.0051(12) C6 0.0437(18) 0.0334(16) 0.0423(15) 0.0045(11) -0.0013(13) 0.0017(13) C7 0.0366(17) 0.0467(17) 0.0380(15) -0.0038(12) -0.0057(12) 0.0042(13) C8 0.059(2) 0.056(2) 0.0553(18) 0.0023(15) -0.0101(16) 0.0054(16) C9 0.0348(18) 0.0532(18) 0.0551(17) -0.0056(14) -0.0021(14) 0.0017(14) N3 0.0446(18) 0.105(2) 0.083(2) -0.0149(19) -0.0029(15) -0.0003(17) C11 0.038(2) 0.131(4) 0.086(3) -0.024(3) -0.016(2) 0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N7 1.949(2) . ? Cu1 N4 1.956(2) 4_576 ? Cu1 N1 2.026(2) . ? Cu1 N2 2.052(2) . ? Cu1 N4 2.440(2) . ? N1 C1 1.323(3) . ? N1 C5 1.338(3) . ? N2 C6 1.274(3) . ? N2 C7 1.428(3) . ? C10 C11 1.351(5) . ? C10 C8 1.352(4) . ? N4 N5 1.205(3) . ? N4 Cu1 1.956(2) 4_575 ? N5 N6 1.150(3) . ? N7 N8 1.194(3) . ? N8 N9 1.147(3) . ? C1 C2 1.388(4) . ? C2 C3 1.367(4) . ? C3 C4 1.381(4) . ? C4 C5 1.370(4) . ? C5 C6 1.473(4) . ? C7 C9 1.377(4) . ? C7 C8 1.386(4) . ? C9 N3 1.349(4) . ? N3 C11 1.359(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 N7 Cu1 N4 97.07(10) . 4_576 ? N7 Cu1 N1 92.58(9) . . ? N4 Cu1 N1 152.12(9) 4_576 . ? N7 Cu1 N2 168.37(9) . . ? N4 Cu1 N2 93.31(8) 4_576 . ? N1 Cu1 N2 80.52(9) . . ? N7 Cu1 N4 86.40(9) . . ? N4 Cu1 N4 115.27(9) 4_576 . ? N1 Cu1 N4 91.33(8) . . ? N2 Cu1 N4 84.42(7) . . ? C1 N1 C5 117.9(2) . . ? C1 N1 Cu1 128.41(19) . . ? C5 N1 Cu1 113.61(17) . . ? C6 N2 C7 120.4(2) . . ? C6 N2 Cu1 112.86(18) . . ? C7 N2 Cu1 126.66(17) . . ? C11 C10 C8 118.8(3) . . ? N5 N4 Cu1 127.87(17) . 4_575 ? N5 N4 Cu1 117.58(16) . . ? Cu1 N4 Cu1 110.73(10) 4_575 . ? N6 N5 N4 176.0(3) . . ? N8 N7 Cu1 125.7(2) . . ? N9 N8 N7 176.1(3) . . ? N1 C1 C2 122.3(3) . . ? C3 C2 C1 119.1(3) . . ? C2 C3 C4 119.1(3) . . ? C5 C4 C3 118.2(3) . . ? N1 C5 C4 123.4(3) . . ? N1 C5 C6 114.3(2) . . ? C4 C5 C6 122.3(2) . . ? N2 C6 C5 118.6(2) . . ? C9 C7 C8 118.7(3) . . ? C9 C7 N2 118.5(2) . . ? C8 C7 N2 122.7(3) . . ? C10 C8 C7 119.2(3) . . ? N3 C9 C7 123.1(3) . . ? C9 N3 C11 115.1(3) . . ? C10 C11 N3 125.0(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.282 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.063 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 671840' #TrackingRef '- DT-ART-06-2012-031186-Rev-CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 Cu N8' _chemical_formula_weight 309.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.818(2) _cell_length_b 19.765(4) _cell_length_c 7.0159(14) _cell_angle_alpha 90.00 _cell_angle_beta 101.68(3) _cell_angle_gamma 90.00 _cell_volume 1333.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28521 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description flake _exptl_crystal_colour green _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 1.638 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.579 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details '(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 0.76 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 21797 _diffrn_reflns_av_R_equivalents 0.0764 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3056 _reflns_number_gt 2289 _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)' _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^)+(0.0569P)^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 0.0044(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3056 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.02204(3) 0.473491(11) 0.25636(4) 0.03992(13) Uani 1 1 d . . . N1 N -0.11893(17) 0.40125(8) 0.1645(2) 0.0343(4) Uani 1 1 d . . . N2 N 0.14919(16) 0.38873(9) 0.3219(2) 0.0371(4) Uani 1 1 d . . . N3 N -0.0916(2) 0.54379(9) 0.0990(3) 0.0435(4) Uani 1 1 d . . . N4 N -0.08869(18) 0.60268(9) 0.1368(3) 0.0400(4) Uani 1 1 d . . . N5 N -0.0900(2) 0.66036(10) 0.1644(3) 0.0599(6) Uani 1 1 d . . . N6 N 0.1234(2) 0.53580(9) 0.4438(3) 0.0515(5) Uani 1 1 d . . . N7 N 0.20295(19) 0.58003(9) 0.4235(3) 0.0420(4) Uani 1 1 d . . . N8 N 0.2799(2) 0.62258(10) 0.4145(4) 0.0672(6) Uani 1 1 d . . . C1 C -0.2536(2) 0.40931(11) 0.0868(3) 0.0430(5) Uani 1 1 d . . . H1 H -0.2882 0.4528 0.0589 0.052 Uiso 1 1 calc R . . C2 C -0.3430(2) 0.35505(12) 0.0469(3) 0.0497(6) Uani 1 1 d . . . H2 H -0.4363 0.3620 -0.0085 0.060 Uiso 1 1 calc R . . C3 C -0.2936(2) 0.29107(12) 0.0891(4) 0.0542(6) Uani 1 1 d . . . H3 H -0.3528 0.2540 0.0640 0.065 Uiso 1 1 calc R . . C4 C -0.1538(3) 0.28218(11) 0.1700(4) 0.0507(6) Uani 1 1 d . . . H4 H -0.1173 0.2392 0.2003 0.061 Uiso 1 1 calc R . . C5 C -0.0711(2) 0.33823(10) 0.2041(3) 0.0377(5) Uani 1 1 d . . . C6 C 0.0802(2) 0.33495(11) 0.2853(3) 0.0438(5) Uani 1 1 d . . . H6 H 0.1242 0.2932 0.3092 0.053 Uiso 1 1 calc R . . C7 C 0.3052(2) 0.38599(11) 0.3894(3) 0.0442(5) Uani 1 1 d . . . C8 C 0.3648(3) 0.31677(13) 0.3584(5) 0.0765(9) Uani 1 1 d . . . H8A H 0.3315 0.2841 0.4393 0.115 Uiso 1 1 calc R . . H8B H 0.4645 0.3186 0.3920 0.115 Uiso 1 1 calc R . . H8C H 0.3361 0.3039 0.2243 0.115 Uiso 1 1 calc R . . C9 C 0.3394(3) 0.40541(16) 0.6027(4) 0.0706(8) Uani 1 1 d . . . H9A H 0.2983 0.4485 0.6198 0.106 Uiso 1 1 calc R . . H9B H 0.4385 0.4083 0.6457 0.106 Uiso 1 1 calc R . . H9C H 0.3031 0.3718 0.6777 0.106 Uiso 1 1 calc R . . C10 C 0.3674(2) 0.43758(13) 0.2699(4) 0.0538(6) Uani 1 1 d . . . H10A H 0.3431 0.4257 0.1346 0.081 Uiso 1 1 calc R . . H10B H 0.4667 0.4378 0.3113 0.081 Uiso 1 1 calc R . . H10C H 0.3314 0.4817 0.2886 0.081 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 0.03582(18) 0.02826(18) 0.0512(2) -0.00016(10) -0.00166(12) -0.00177(10) N1 0.0328(9) 0.0329(9) 0.0365(10) 0.0012(7) 0.0054(7) -0.0014(7) N2 0.0300(9) 0.0368(9) 0.0428(11) 0.0039(8) 0.0034(7) 0.0001(7) N3 0.0494(11) 0.0311(9) 0.0476(11) 0.0038(8) 0.0038(9) 0.0013(8) N4 0.0404(10) 0.0350(10) 0.0462(11) 0.0011(8) 0.0123(8) -0.0001(8) N5 0.0687(15) 0.0355(11) 0.0776(16) -0.0049(10) 0.0199(12) -0.0007(10) N6 0.0588(13) 0.0443(11) 0.0498(12) -0.0081(9) 0.0073(10) -0.0158(9) N7 0.0413(10) 0.0347(9) 0.0474(11) -0.0063(8) 0.0029(8) 0.0005(8) N8 0.0626(14) 0.0504(12) 0.0871(18) -0.0057(11) 0.0117(12) -0.0209(11) C1 0.0347(11) 0.0450(12) 0.0471(13) 0.0035(10) 0.0027(9) 0.0003(9) C2 0.0347(11) 0.0565(14) 0.0549(15) -0.0037(11) 0.0018(10) -0.0050(10) C3 0.0422(13) 0.0456(13) 0.0727(18) -0.0054(12) 0.0062(12) -0.0143(10) C4 0.0446(13) 0.0353(12) 0.0705(18) -0.0007(11) 0.0076(12) -0.0036(9) C5 0.0345(11) 0.0330(11) 0.0453(13) 0.0008(9) 0.0075(9) -0.0012(8) C6 0.0371(12) 0.0328(11) 0.0604(15) 0.0061(10) 0.0075(10) 0.0061(9) C7 0.0285(11) 0.0460(13) 0.0547(14) 0.0072(10) 0.0005(9) 0.0032(9) C8 0.0409(15) 0.0568(16) 0.127(3) 0.0086(16) 0.0055(16) 0.0110(12) C9 0.0404(14) 0.118(2) 0.0497(16) 0.0141(15) -0.0003(11) -0.0027(15) C10 0.0346(12) 0.0656(15) 0.0617(16) 0.0063(12) 0.0108(11) -0.0014(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 Cu1 N6 1.9252(19) . ? Cu1 N3 1.9734(19) . ? Cu1 N1 2.0021(16) . ? Cu1 N2 2.0843(17) . ? N1 C1 1.334(3) . ? N1 C5 1.340(3) . ? N2 C6 1.259(3) . ? N2 C7 1.509(3) . ? N3 N4 1.193(2) . ? N4 N5 1.157(2) . ? N6 N7 1.200(2) . ? N7 N8 1.141(3) . ? C1 C2 1.378(3) . ? C2 C3 1.365(3) . ? C3 C4 1.386(4) . ? C4 C5 1.366(3) . ? C5 C6 1.481(3) . ? C7 C9 1.515(4) . ? C7 C8 1.521(3) . ? C7 C10 1.524(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 N6 Cu1 N3 95.00(9) . . ? N6 Cu1 N1 154.70(8) . . ? N3 Cu1 N1 92.67(8) . . ? N6 Cu1 N2 99.19(8) . . ? N3 Cu1 N2 159.20(8) . . ? N1 Cu1 N2 80.90(7) . . ? C1 N1 C5 118.19(18) . . ? C1 N1 Cu1 127.58(14) . . ? C5 N1 Cu1 113.93(14) . . ? C6 N2 C7 120.24(18) . . ? C6 N2 Cu1 111.12(14) . . ? C7 N2 Cu1 128.48(13) . . ? N4 N3 Cu1 125.28(16) . . ? N5 N4 N3 176.6(2) . . ? N7 N6 Cu1 130.09(17) . . ? N8 N7 N6 176.4(2) . . ? N1 C1 C2 121.9(2) . . ? C3 C2 C1 119.6(2) . . ? C2 C3 C4 119.0(2) . . ? C5 C4 C3 118.2(2) . . ? N1 C5 C4 123.1(2) . . ? N1 C5 C6 113.74(17) . . ? C4 C5 C6 123.11(19) . . ? N2 C6 C5 119.87(18) . . ? N2 C7 C9 107.99(19) . . ? N2 C7 C8 112.52(19) . . ? C9 C7 C8 110.7(2) . . ? N2 C7 C10 107.30(17) . . ? C9 C7 C10 109.9(2) . . ? C8 C7 C10 108.3(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.374 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.063 #===END