Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Konstantin V. Domasevitch' _publ_contact_author_address ; Inorganic Chemistry Department Kiev University Volodimirska Str. 64 Kiev 01033 UKRAINE ; _publ_contact_author_phone ? _publ_contact_author_fax +380(44)296-2467 _publ_contact_author_email dk@anorgchemie.univ.kiev.ua _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Fused pyridazines: rigid multidentates for design and fine-tuning the structure of hybrid organic/inorganic frameworks ; loop_ _publ_author_name _publ_author_address P.V.Solntsev ; Inorganic Chemistry Department Kiev Shevchenko University Volodimirska Str. 64 01033 Kiev Ukraine ; J.Sieler ; Institute of Inorganic Chemistry Leipzig University Linnestrasse 3 D-04103 Leipzig Germany ; H.Krautscheid ; Institute of Inorganic Chemistry Leipzig University Linnestrasse 3 D-04103 Leipzig Germany ; K.V.Domasevitch ; Inorganic Chemistry Department Kiev Shevchenko University Volodimirska Str. 64 01033 Kiev Ukraine ; _publ_section_acknowledgements ; KVD and JS acknowledge support from Deutsche Forschungsgemeinschaft; and from INTAS Fellowship 2002-310 (KVD). ; #============================================================================== data_c1424 _database_code_depnum_ccdc_archive 'CCDC 227199' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I) Bromide 2:1 Complex with 1,2,3,6,7,8-Hexahydro-cinnolino[5,4,3-cde]cinnoline, dichloromethane solvate ; _chemical_name_common ; Copper(i) Bromide 2:1 Complex with 1,2,3,6,7,8-Hexahydro- cinnolino(5,4,3-cde)cinnoline, dichloromethane solvate ; _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 Br2 Cl2 Cu2 N4' _chemical_formula_weight 584.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)md loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x, -y, z' '-x+1/2, y+1/2, z+1/2' '-y, -x+1/2, z+1/4' 'y+1/2, x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' 'x+1/2, -y+1/2, z+1/2' '-x+1, y+1, z+1' '-y+1/2, -x+1, z+3/4' 'y+1, x+1/2, z+5/4' _cell_length_a 17.7304(19) _cell_length_b 17.7304(19) _cell_length_c 12.6008(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3961.3(7) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour dark-brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 6.453 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3896 _exptl_absorpt_correction_T_max 0.5647 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Seimens SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13973 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 28.70 _reflns_number_total 2554 _reflns_number_gt 1795 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0890P)^2^+4.5807P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.38(3) _refine_ls_number_reflns 2554 _refine_ls_number_parameters 108 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1563 _refine_ls_wR_factor_gt 0.1447 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.26131(6) 0.26231(6) 0.08659(13) 0.0279(2) Uani 1 d . . . Br1 Br 0.15607(4) 0.24154(6) 0.21140(9) 0.0454(3) Uani 1 d . . . N1 N 0.3655(4) 0.2613(4) 0.1599(6) 0.0283(16) Uani 1 d . . . N2 N 0.3661(5) 0.2510(4) 0.2683(8) 0.0306(18) Uani 1 d . . . C1 C 0.4322(7) 0.2479(5) 0.3213(9) 0.041(3) Uani 1 d . . . C2 C 0.5000 0.2548(7) 0.2683(12) 0.035(3) Uani 1 d S . . C3 C 0.5000 0.2637(7) 0.1584(9) 0.025(2) Uani 1 d S . . C4 C 0.4291(5) 0.2667(6) 0.1068(6) 0.0294(18) Uani 1 d . . . C5 C 0.4307(6) 0.2369(8) 0.4374(8) 0.056(3) Uani 1 d . . . H5A H 0.4232 0.1848 0.4552 0.080 Uiso 1 d R . . H5B H 0.3888 0.2650 0.4651 0.080 Uiso 1 d R . . C6 C 0.5000 0.2651(12) 0.4882(10) 0.057(5) Uani 1 d S . . H6A H 0.5000 0.2499 0.5613 0.080 Uiso 1 d SR . . H6B H 0.5000 0.3193 0.4867 0.080 Uiso 1 d SR . . C7 C 0.4281(5) 0.2831(9) -0.0131(7) 0.056(3) Uani 1 d . . . H7A H 0.4142 0.3349 -0.0238 0.080 Uiso 1 d R . . H7B H 0.3912 0.2520 -0.0477 0.080 Uiso 1 d R . . C8 C 0.5000 0.266(2) -0.0610(17) 0.099(9) Uani 1 d S . . H8A H 0.5000 0.2939 -0.1265 0.080 Uiso 1 d SR . . H8B H 0.5000 0.2139 -0.0803 0.080 Uiso 1 d SR . . C10 C 0.4243(14) 0.5000 -0.139(2) 0.046(6) Uiso 0.50 d SP . . C11 C 0.4449(14) 0.4193(13) -0.224(2) 0.056(5) Uiso 0.50 d P . . C12 C 0.5295(10) 0.4204(10) -0.2655(17) 0.046(4) Uiso 0.50 d P . . 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 0.0317(6) 0.0286(6) 0.0235(3) 0.0048(6) -0.0006(6) 0.0004(3) Br1 0.0299(4) 0.0816(7) 0.0246(3) 0.0001(4) 0.0007(5) -0.0044(4) N1 0.024(4) 0.046(4) 0.015(4) 0.000(3) 0.006(3) 0.003(3) N2 0.028(5) 0.037(4) 0.026(4) 0.003(2) 0.004(3) -0.003(2) C1 0.038(6) 0.055(6) 0.030(5) 0.000(3) -0.006(4) 0.006(3) C2 0.030(7) 0.048(7) 0.027(7) 0.014(5) 0.000 0.000 C3 0.017(6) 0.043(6) 0.014(5) 0.002(4) 0.000 0.000 C4 0.015(4) 0.061(5) 0.013(4) 0.002(3) -0.003(3) 0.007(3) C5 0.023(4) 0.126(10) 0.021(4) 0.011(5) 0.007(3) -0.002(5) C6 0.027(7) 0.137(15) 0.007(6) -0.005(6) 0.000 0.000 C7 0.033(5) 0.112(9) 0.024(5) 0.024(5) -0.001(3) -0.003(6) C8 0.049(12) 0.21(3) 0.034(11) -0.010(11) 0.000 0.000 _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 N2 2.042(8) 11_544 ? Cu1 N1 2.066(8) . ? Cu1 Br1 2.4575(18) 11_544 ? Cu1 Br1 2.4679(17) . ? Br1 Cu1 2.4575(18) 12_454 ? N1 C4 1.314(12) . ? N1 N2 1.379(7) . ? N2 C1 1.350(16) . ? N2 Cu1 2.042(8) 12_454 ? C1 C2 1.381(16) . ? C1 C5 1.476(15) . ? C2 C1 1.381(16) 14_544 ? C2 C3 1.393(11) . ? C3 C4 1.416(10) . ? C3 C4 1.416(10) 14_544 ? C4 C7 1.539(12) . ? C5 C6 1.473(16) . ? C6 C5 1.473(16) 14_544 ? C7 C8 1.441(16) . ? C8 C7 1.441(16) 14_544 ? C10 C11 1.83(3) . ? C10 C11 1.83(3) 5_565 ? C11 C12 0.69(2) 14_544 ? C11 C12 1.59(3) . ? C11 C11 1.95(5) 14_544 ? C12 C11 0.69(2) 14_544 ? C12 C12 1.05(4) 14_544 ? 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 N2 Cu1 N1 107.0(3) 11_544 . ? N2 Cu1 Br1 114.7(3) 11_544 11_544 ? N1 Cu1 Br1 107.4(2) . 11_544 ? N2 Cu1 Br1 108.8(2) 11_544 . ? N1 Cu1 Br1 113.0(2) . . ? Br1 Cu1 Br1 106.21(3) 11_544 . ? Cu1 Br1 Cu1 80.36(2) 12_454 . ? C4 N1 N2 120.5(9) . . ? C4 N1 Cu1 122.6(6) . . ? N2 N1 Cu1 116.8(7) . . ? C1 N2 N1 120.1(9) . . ? C1 N2 Cu1 124.7(8) . 12_454 ? N1 N2 Cu1 115.2(7) . 12_454 ? N2 C1 C2 120.9(12) . . ? N2 C1 C5 118.7(10) . . ? C2 C1 C5 120.4(11) . . ? C1 C2 C1 121.1(15) 14_544 . ? C1 C2 C3 119.4(8) 14_544 . ? C1 C2 C3 119.4(8) . . ? C2 C3 C4 117.4(6) . . ? C2 C3 C4 117.4(6) . 14_544 ? C4 C3 C4 125.2(11) . 14_544 ? N1 C4 C3 121.7(9) . . ? N1 C4 C7 120.3(7) . . ? C3 C4 C7 117.9(8) . . ? C6 C5 C1 111.8(10) . . ? C5 C6 C5 113.0(15) . 14_544 ? C8 C7 C4 111.3(11) . . ? C7 C8 C7 124.3(19) . 14_544 ? C11 C10 C11 103(2) . 5_565 ? C12 C11 C12 29.7(19) 14_544 . ? C12 C11 C10 124(3) 14_544 . ? C12 C11 C10 111.8(17) . . ? C12 C11 C11 49(3) 14_544 14_544 ? C12 C11 C11 19.0(10) . 14_544 ? C10 C11 C11 101.5(11) . 14_544 ? C11 C12 C12 131(3) 14_544 14_544 ? C11 C12 C11 112(3) 14_544 . ? C12 C12 C11 19.0(10) 14_544 . ? _diffrn_measured_fraction_theta_max 0.509 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.509 _refine_diff_density_max 1.519 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.138 #============================================================================== data_c1557 _database_code_depnum_ccdc_archive 'CCDC 227200' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I) Bromide 2:1 Complex with 1,2,3,6,7,8-Hexahydro-cinnolino[5,4,3-cde]cinnoline ; _chemical_name_common ; Copper(i) Bromide 2:1 Complex with 1,2,3,6,7,8-Hexahydro- cinnolino(5,4,3-cde)cinnoline ; _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Br2 Cu2 N4' _chemical_formula_weight 499.16 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' '-x+1/2, y, -z+3/4' 'x, -y+1/2, -z+1/4' 'y+1/2, x+1/2, -z+1/2' '-y, -x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' '-x+1, y+1/2, -z+5/4' 'x+1/2, -y+1, -z+3/4' 'y+1, x+1, -z+1' '-y+1/2, -x+1/2, -z+1/2' _cell_length_a 12.3176(11) _cell_length_b 12.3176(11) _cell_length_c 12.772(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1937.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour dark-brown _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 6.313 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.2160 _exptl_absorpt_correction_T_max 0.4941 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5730 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0103 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 29.10 _reflns_number_total 1217 _reflns_number_gt 1202 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+8.9120P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.53(3) _refine_ls_number_reflns 1217 _refine_ls_number_parameters 52 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.85149(3) 0.85149(3) 0.0000 0.02518(15) Uani 1 d S . . Cu1 Cu 0.7500 0.73539(5) -0.1250 0.01959(16) Uani 1 d S . . N1 N 0.8614(3) 0.6357(3) -0.1956(2) 0.0222(6) Uani 1 d . . . C1 C 0.9260(4) 0.5695(4) -0.1433(3) 0.0245(7) Uani 1 d . . . C2 C 1.0000 0.5000 -0.1959(3) 0.0209(9) Uani 1 d S . . C3 C 0.9210(6) 0.5660(5) -0.0255(3) 0.0434(13) Uani 1 d . . . C4 C 1.0232(10) 0.5303(8) 0.0189(5) 0.040(2) Uani 0.50 d P . . 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 Br1 0.02938(19) 0.02938(19) 0.0168(2) -0.00055(18) 0.00055(18) -0.0096(2) Cu1 0.0210(3) 0.0226(3) 0.0152(2) 0.000 0.0026(2) 0.000 N1 0.0277(16) 0.0231(16) 0.0156(13) 0.0002(12) 0.0053(13) 0.0080(11) C1 0.032(2) 0.0298(19) 0.0115(13) -0.0005(15) 0.0004(15) 0.0122(13) C2 0.028(3) 0.024(3) 0.011(2) 0.000 0.000 0.0093(18) C3 0.066(3) 0.053(3) 0.0115(16) 0.0037(18) 0.0031(19) 0.040(2) C4 0.059(7) 0.045(6) 0.015(3) -0.008(3) -0.005(3) 0.029(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Cu1 2.4813(6) . ? Br1 Cu1 2.4813(6) 12_464 ? Cu1 N1 2.051(3) 5_654 ? Cu1 N1 2.051(3) . ? Cu1 Br1 2.4813(6) 11_644 ? N1 C1 1.320(4) . ? N1 N1 1.390(5) 16_664 ? C1 C2 1.419(4) . ? C1 C3 1.507(4) . ? C2 C2 1.382(8) 7_544 ? C2 C1 1.419(4) 10_654 ? C3 C4 1.449(12) . ? C3 C4 1.483(11) 10_654 ? C4 C4 0.94(2) 10_654 ? C4 C3 1.483(11) 10_654 ? 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 Cu1 Br1 Cu1 80.40(2) . 12_464 ? N1 Cu1 N1 106.4(2) 5_654 . ? N1 Cu1 Br1 113.55(8) 5_654 . ? N1 Cu1 Br1 106.91(10) . . ? N1 Cu1 Br1 106.91(10) 5_654 11_644 ? N1 Cu1 Br1 113.55(8) . 11_644 ? Br1 Cu1 Br1 109.61(3) . 11_644 ? C1 N1 N1 120.39(18) . 16_664 ? C1 N1 Cu1 123.4(2) . . ? N1 N1 Cu1 116.18(8) 16_664 . ? N1 C1 C2 121.3(3) . . ? N1 C1 C3 119.9(3) . . ? C2 C1 C3 118.8(3) . . ? C2 C2 C1 118.2(2) 7_544 . ? C2 C2 C1 118.2(2) 7_544 10_654 ? C1 C2 C1 123.6(4) . 10_654 ? C4 C3 C4 37.3(7) . 10_654 ? C4 C3 C1 111.3(5) . . ? C4 C3 C1 112.7(4) 10_654 . ? C4 C4 C3 73.3(13) 10_654 . ? C4 C4 C3 69.4(12) 10_654 10_654 ? C3 C4 C3 119.8(6) . 10_654 ? _diffrn_measured_fraction_theta_max 0.466 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.466 _refine_diff_density_max 0.999 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.108 #============================================================================== data_c1558 _database_code_depnum_ccdc_archive 'CCDC 227201' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I) Iodide 2:1 Complex with 1,2,3,6,7,8-Hexahydro-cinnolino[5,4,3-cde]cinnoline ; _chemical_name_common ; Copper(i) Iodide 2:1 Complex with 1,2,3,6,7,8-Hexahydro- cinnolino(5,4,3-cde)cinnoline ; _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cu2 I2 N4' _chemical_formula_weight 593.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' '-x+1/2, y, -z+3/4' 'x, -y+1/2, -z+1/4' 'y+1/2, x+1/2, -z+1/2' '-y, -x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' '-x+1, y+1/2, -z+5/4' 'x+1/2, -y+1, -z+3/4' 'y+1, x+1, -z+1' '-y+1/2, -x+1/2, -z+1/2' _cell_length_a 12.3475(10) _cell_length_b 12.3475(10) _cell_length_c 13.2122(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2014.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour dark-brown _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.956 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 5.172 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.2647 _exptl_absorpt_correction_T_max 0.5529 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5437 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 29.17 _reflns_number_total 1251 _reflns_number_gt 1244 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+10.5120P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.50(6) _refine_ls_number_reflns 1251 _refine_ls_number_parameters 52 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0272 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0699 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.860631(19) 0.860631(19) 0.0000 0.02275(12) Uani 1 d S . . Cu1 Cu 0.7500 0.73492(6) -0.1250 0.01751(15) Uani 1 d S . . N1 N 0.8604(3) 0.6345(3) -0.1976(2) 0.0177(6) Uani 1 d . . . C1 C 0.9246(4) 0.5676(4) -0.1470(3) 0.0186(7) Uani 1 d . . . C2 C 1.0000 0.5000 -0.1979(4) 0.0162(9) Uani 1 d S . . C3 C 0.9183(5) 0.5622(5) -0.0333(3) 0.0324(12) Uani 1 d . . . C4 C 1.0259(9) 0.5340(8) 0.0104(7) 0.0334(19) Uani 0.50 d P . . 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 I1 0.02733(14) 0.02733(14) 0.01360(17) -0.00044(13) 0.00044(13) -0.00968(14) Cu1 0.0184(3) 0.0211(3) 0.0131(3) 0.000 0.0016(2) 0.000 N1 0.0235(16) 0.0205(16) 0.0092(14) 0.0020(13) 0.0022(13) 0.0064(12) C1 0.026(2) 0.0236(19) 0.0061(14) 0.0006(14) 0.0022(14) 0.0094(14) C2 0.022(3) 0.017(3) 0.009(2) 0.000 0.000 0.0062(17) C3 0.047(3) 0.046(3) 0.0035(14) 0.0038(18) 0.0040(18) 0.028(2) C4 0.046(6) 0.041(5) 0.013(4) -0.008(4) -0.006(4) 0.023(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Cu1 2.6463(5) . ? I1 Cu1 2.6463(5) 12_464 ? Cu1 N1 2.078(3) 5_654 ? Cu1 N1 2.078(3) . ? Cu1 I1 2.6463(5) 11_644 ? N1 C1 1.326(5) . ? N1 N1 1.386(6) 16_664 ? C1 C2 1.420(4) . ? C1 C3 1.505(5) . ? C2 C2 1.378(10) 7_544 ? C2 C1 1.420(4) 10_654 ? C3 C4 1.490(11) 10_654 ? C3 C4 1.490(12) . ? C4 C4 1.06(2) 10_654 ? C4 C3 1.490(11) 10_654 ? 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 Cu1 I1 Cu1 77.521(17) . 12_464 ? N1 Cu1 N1 106.7(2) 5_654 . ? N1 Cu1 I1 113.61(8) 5_654 . ? N1 Cu1 I1 107.43(11) . . ? N1 Cu1 I1 107.43(11) 5_654 11_644 ? N1 Cu1 I1 113.61(8) . 11_644 ? I1 Cu1 I1 108.17(3) . 11_644 ? C1 N1 N1 120.3(2) . 16_664 ? C1 N1 Cu1 122.0(2) . . ? N1 N1 Cu1 117.62(8) 16_664 . ? N1 C1 C2 121.2(3) . . ? N1 C1 C3 120.0(3) . . ? C2 C1 C3 118.7(3) . . ? C2 C2 C1 118.3(2) 7_544 . ? C2 C2 C1 118.3(2) 7_544 10_654 ? C1 C2 C1 123.4(4) . 10_654 ? C4 C3 C4 41.5(8) 10_654 . ? C4 C3 C1 113.5(5) 10_654 . ? C4 C3 C1 110.6(5) . . ? C4 C4 C3 69.2(10) 10_654 10_654 ? C4 C4 C3 69.3(10) 10_654 . ? C3 C4 C3 116.6(7) 10_654 . ? _diffrn_measured_fraction_theta_max 0.463 _diffrn_reflns_theta_full 29.17 _diffrn_measured_fraction_theta_full 0.463 _refine_diff_density_max 1.063 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.119 #============================================================================== data_c1721 _database_code_depnum_ccdc_archive 'CCDC 227202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I) Iodide 2:1 Complex with 1,2,3,6,7,8-Hexahydro-cinnolino[5,4,3-cde]cinnoline, chloroform solvate ; _chemical_name_common ; Copper(i) Iodide 2:1 Complex with 1,2,3,6,7,8-Hexahydro- cinnolino(5,4,3-cde)cinnoline, chloroform solvate ; _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 Cl3 Cu2 I2 N4' _chemical_formula_weight 712.50 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/amd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+1/4, x+3/4, z+1/4' 'y+1/4, -x+1/4, z+3/4' '-x+1/2, y, -z+1/2' 'x, -y, -z' 'y+1/4, x+3/4, -z+1/4' '-y+1/4, -x+1/4, -z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+3/4, x+5/4, z+3/4' 'y+3/4, -x+3/4, z+5/4' '-x+1, y+1/2, -z+1' 'x+1/2, -y+1/2, -z+1/2' 'y+3/4, x+5/4, -z+3/4' '-y+3/4, -x+3/4, -z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-1/4, -x-3/4, -z-1/4' '-y-1/4, x-1/4, -z-3/4' 'x-1/2, -y, z-1/2' '-x, y, z' '-y-1/4, -x-3/4, z-1/4' 'y-1/4, x-1/4, z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y+1/4, -x-1/4, -z+1/4' '-y+1/4, x+1/4, -z-1/4' 'x, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' '-y+1/4, -x-1/4, z+1/4' 'y+1/4, x+1/4, z-1/4' _cell_length_a 17.614(2) _cell_length_b 17.614(2) _cell_length_c 13.136(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4075.5(10) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour black-brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2672 _exptl_absorpt_coefficient_mu 5.514 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.4051 _exptl_absorpt_correction_T_max 0.6086 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11844 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.88 _reflns_number_total 1295 _reflns_number_gt 1120 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+65.0498P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1295 _refine_ls_number_parameters 61 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.265 _refine_ls_restrained_S_all 1.264 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.35594(3) 0.5000 0.0000 0.0402(2) Uani 1 d S . . Cu1 Cu 0.24070(4) 0.50930(4) 0.1250 0.0223(2) Uani 1 d S . . N1 N 0.1358(3) 0.5067(3) 0.0525(3) 0.0212(9) Uani 1 d . . . C1 C 0.0712(3) 0.5132(4) 0.1020(4) 0.0264(12) Uani 1 d . . . C2 C 0.0000 0.5073(5) 0.0514(5) 0.0216(15) Uani 1 d S . . C3 C 0.0712(4) 0.5280(5) 0.2149(5) 0.0435(19) Uani 1 d . . . H3A H 0.0764 0.5816 0.2261 0.080 Uiso 1 d R . . H3B H 0.1140 0.5032 0.2455 0.080 Uiso 1 d R . . C4 C 0.0000 0.5027(10) 0.2645(6) 0.059(4) Uani 1 d S . . H4A H 0.0000 0.5187 0.3344 0.080 Uiso 1 d SR . . H4B H 0.0000 0.4482 0.2639 0.080 Uiso 1 d SR . . Cl1 Cl 0.0589(13) 0.6759(16) 0.4034(18) 0.267(9) Uiso 0.50 d PD . . C10 C 0.018(2) 0.7500 0.337(3) 0.9(5) Uiso 0.50 d SPD . . Cl2 Cl -0.0796(18) 0.7500 0.354(4) 0.349(19) Uiso 0.50 d SPD . . 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 I1 0.0236(3) 0.0775(5) 0.0194(3) 0.0011(3) 0.000 0.000 Cu1 0.0243(3) 0.0243(3) 0.0183(4) -0.0015(2) -0.0015(2) -0.0007(4) N1 0.020(2) 0.031(2) 0.0120(19) -0.0036(19) 0.0005(16) 0.002(2) C1 0.018(2) 0.046(4) 0.015(2) -0.004(2) 0.0002(19) -0.001(2) C2 0.014(3) 0.036(4) 0.015(3) -0.004(3) 0.000 0.000 C3 0.024(3) 0.091(6) 0.015(2) -0.014(3) -0.002(2) 0.002(3) C4 0.035(5) 0.129(12) 0.013(4) -0.008(6) 0.000 0.000 _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 I1 Cu1 2.6160(8) 11_544 ? I1 Cu1 2.6160(8) . ? Cu1 N1 2.080(4) . ? Cu1 N1 2.080(4) 16_554 ? Cu1 I1 2.6160(8) 12_454 ? N1 C1 1.315(7) . ? N1 N1 1.400(8) 6_565 ? C1 C2 1.424(6) . ? C1 C3 1.505(8) . ? C2 C2 1.374(14) 17_565 ? C2 C1 1.424(6) 22 ? C3 C4 1.482(9) . ? C4 C3 1.482(9) 22 ? Cl1 Cl2 1.50(3) 10_464 ? Cl1 C10 1.729(10) . ? Cl1 C10 2.07(4) 10_464 ? Cl1 Cl1 2.08(5) 22 ? C10 C10 0.63(7) 10_464 ? C10 Cl2 1.11(7) 10_464 ? C10 Cl1 1.729(10) 29_565 ? C10 Cl2 1.730(10) . ? C10 Cl1 2.07(4) 22 ? C10 Cl1 2.07(4) 10_464 ? Cl2 C10 1.11(7) 10_464 ? Cl2 Cl1 1.50(3) 10_464 ? Cl2 Cl1 1.50(3) 22 ? 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 Cu1 I1 Cu1 78.22(3) 11_544 . ? N1 Cu1 N1 104.4(3) . 16_554 ? N1 Cu1 I1 109.01(13) . 12_454 ? N1 Cu1 I1 113.63(11) 16_554 12_454 ? N1 Cu1 I1 113.63(11) . . ? N1 Cu1 I1 109.01(13) 16_554 . ? I1 Cu1 I1 107.26(3) 12_454 . ? C1 N1 N1 120.2(3) . 6_565 ? C1 N1 Cu1 122.7(3) . . ? N1 N1 Cu1 117.07(12) 6_565 . ? N1 C1 C2 121.6(5) . . ? N1 C1 C3 120.2(5) . . ? C2 C1 C3 118.2(5) . . ? C2 C2 C1 118.2(3) 17_565 . ? C2 C2 C1 118.2(3) 17_565 22 ? C1 C2 C1 123.5(6) . 22 ? C4 C3 C1 112.4(6) . . ? C3 C4 C3 115.6(10) 22 . ? Cl2 Cl1 C10 39(3) 10_464 . ? Cl2 Cl1 C10 55.2(12) 10_464 10_464 ? C10 Cl1 C10 15.9(17) . 10_464 ? Cl2 Cl1 Cl1 104(2) 10_464 22 ? C10 Cl1 Cl1 65.2(10) . 22 ? C10 Cl1 Cl1 49.3(11) 10_464 22 ? C10 C10 Cl2 168(2) 10_464 10_464 ? C10 C10 Cl1 114.8(10) 10_464 29_565 ? Cl2 C10 Cl1 59.2(18) 10_464 29_565 ? C10 C10 Cl1 114.8(10) 10_464 . ? Cl2 C10 Cl1 59.2(18) 10_464 . ? Cl1 C10 Cl1 98(3) 29_565 . ? C10 C10 Cl2 7.4(16) 10_464 . ? Cl2 C10 Cl2 161(4) 10_464 . ? Cl1 C10 Cl2 110.6(9) 29_565 . ? Cl1 C10 Cl2 110.6(9) . . ? C10 C10 Cl1 49.3(11) 10_464 22 ? Cl2 C10 Cl1 123.7(19) 10_464 22 ? Cl1 C10 Cl1 122(3) 29_565 22 ? Cl1 C10 Cl1 65.5(12) . 22 ? Cl2 C10 Cl1 45.5(11) . 22 ? C10 C10 Cl1 49.3(11) 10_464 10_464 ? Cl2 C10 Cl1 123.7(19) 10_464 10_464 ? Cl1 C10 Cl1 65.5(12) 29_565 10_464 ? Cl1 C10 Cl1 122(3) . 10_464 ? Cl2 C10 Cl1 45.5(11) . 10_464 ? Cl1 C10 Cl1 78(2) 22 10_464 ? C10 Cl2 Cl1 81(2) 10_464 10_464 ? C10 Cl2 Cl1 81(2) 10_464 22 ? Cl1 Cl2 Cl1 121(4) 10_464 22 ? C10 Cl2 C10 4.1(8) 10_464 . ? Cl1 Cl2 C10 79.3(18) 10_464 . ? Cl1 Cl2 C10 79.3(19) 22 . ? _diffrn_measured_fraction_theta_max 0.462 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.462 _refine_diff_density_max 1.225 _refine_diff_density_min -0.859 _refine_diff_density_rms 0.137 #============================================================================== data_c1552 _database_code_depnum_ccdc_archive 'CCDC 227203' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I) Iodide 3:1 Complex with 1,2,3,6,7,8-Hexahydro-cinnolino[5,4,3-cde]cinnoline, acetonitrile solvate ; _chemical_name_common ; Copper(i) Iodide 3:1 Complex with 1,2,3,6,7,8-Hexahydro- cinnolino(5,4,3-cde)cinnoline, acetonitrile solvate ; _chemical_formula_moiety ? _chemical_formula_sum 'C80 H84 Cu18 I18 N28' _chemical_formula_weight 4865.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(3)/mmc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' 'y, x, -z' 'x-y, -y, -z' '-x, -x+y, -z' '-y, -x, -z+1/2' '-x+y, y, -z+1/2' 'x, x-y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z-1/2' 'x-y, -y, z-1/2' '-x, -x+y, z-1/2' _cell_length_a 20.463(2) _cell_length_b 20.463(2) _cell_length_c 17.989(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6523.6(12) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'hexagonal prism' _exptl_crystal_colour brown _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4472 _exptl_absorpt_coefficient_mu 7.171 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.1407 _exptl_absorpt_correction_T_max 0.2672 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38755 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0126 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2792 _reflns_number_gt 2417 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+62.2325P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2792 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.178 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.09222(4) 0.34004(4) 0.48494(3) 0.02075(17) Uani 1 d . . . Cu2 Cu 0.59578(6) 0.19155(12) 0.7500 0.0475(5) Uani 1 d S . . Cu3 Cu -0.12343(7) 0.12343(7) 0.42372(13) 0.0372(5) Uani 0.50 d SP . . I1 I 0.0000 0.19454(3) 0.5000 0.02935(16) Uani 1 d S . . I2 I 0.194888(17) 0.38978(3) 0.59218(3) 0.03047(17) Uani 1 d S . . I3 I 0.52485(5) 0.26242(3) 0.7500 0.0426(2) Uani 1 d S . . I4 I 0.52490(4) 0.04981(8) 0.7500 0.0704(4) Uani 1 d S . . N1 N 0.1358(2) 0.3398(2) 0.3820(2) 0.0165(8) Uani 1 d . . . N2 N 0.0377(2) 0.4019(2) 0.4894(2) 0.0170(8) Uani 1 d . . . N3 N -0.0976(8) 0.0976(8) 0.3221(8) 0.061(6) Uani 0.50 d SP . . C1 C 0.0997(3) 0.3326(3) 0.3189(3) 0.0181(9) Uani 1 d . . . C2 C 0.1311(4) 0.3292(4) 0.2500 0.0182(13) Uani 1 d S . . C3 C 0.0264(3) 0.3330(4) 0.3208(3) 0.0249(11) Uani 1 d . . . H3A H 0.0365 0.3841 0.3244 0.080 Uiso 1 d R . . H3B H -0.0020 0.3060 0.3638 0.080 Uiso 1 d R . . C4 C -0.0198(4) 0.2962(6) 0.2500 0.0273(17) Uani 1 d S . . H4A H -0.0642 0.3009 0.2500 0.080 Uiso 1 d SR . . H4B H -0.0356 0.2435 0.2500 0.080 Uiso 1 d SR . . C5 C 0.0738(3) 0.4762(3) 0.4775(3) 0.0190(9) Uani 1 d . . . C6 C 0.0372(4) 0.51859(19) 0.4880(4) 0.0171(13) Uani 1 d S . . C7 C 0.1540(3) 0.5148(3) 0.4510(4) 0.0307(13) Uani 1 d . . . H7A H 0.1546 0.5093 0.3980 0.080 Uiso 1 d R . . H7B H 0.1794 0.4909 0.4730 0.080 Uiso 1 d R . . C8 C 0.1957(5) 0.5978(3) 0.4707(7) 0.042(2) Uani 1 d S . . H8A H 0.2435 0.6218 0.4456 0.080 Uiso 1 d SR . . H8B H 0.2055 0.6028 0.5232 0.080 Uiso 1 d SR . . C9 C -0.0904(8) 0.0904(8) 0.2500 0.084(7) Uani 1 d S . . N4 N 0.0000 0.0000 0.289(4) 0.101(17) Uiso 0.50 d SP . . C10 C 0.0000 0.0000 0.349(5) 0.10(2) Uiso 0.50 d SP . . C11 C 0.0000 0.0000 0.440(5) 0.092(19) Uiso 0.50 d SP . . 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 0.0212(3) 0.0228(3) 0.0205(3) 0.0000(2) 0.0031(2) 0.0127(3) Cu2 0.0449(8) 0.0487(11) 0.0500(10) 0.000 0.000 0.0244(5) Cu3 0.0395(9) 0.0395(9) 0.0324(10) -0.0016(5) 0.0016(5) 0.0197(10) I1 0.0234(3) 0.0246(2) 0.0396(3) 0.00114(11) 0.0023(2) 0.01172(13) I2 0.0294(2) 0.0423(3) 0.0240(3) -0.0045(2) -0.00223(11) 0.02116(16) I3 0.0278(4) 0.0345(3) 0.0632(6) 0.000 0.000 0.0139(2) I4 0.0467(4) 0.0613(7) 0.1081(11) 0.000 0.000 0.0307(4) N1 0.016(2) 0.019(2) 0.0161(17) 0.0008(16) 0.0008(15) 0.0102(17) N2 0.015(2) 0.0159(19) 0.0200(19) 0.0019(15) 0.0043(16) 0.0078(17) N3 0.070(9) 0.070(9) 0.010(6) 0.009(4) -0.009(4) 0.010(11) C1 0.017(2) 0.023(2) 0.015(2) 0.0013(18) 0.0027(18) 0.010(2) C2 0.016(3) 0.022(3) 0.017(3) 0.000 0.000 0.010(3) C3 0.018(2) 0.045(3) 0.016(2) -0.001(2) -0.0001(19) 0.019(2) C4 0.015(3) 0.049(5) 0.019(3) 0.000 0.000 0.017(3) C5 0.017(2) 0.018(2) 0.022(2) 0.0031(19) 0.0057(18) 0.0079(19) C6 0.014(3) 0.018(2) 0.018(3) 0.0019(13) 0.004(3) 0.0072(17) C7 0.018(3) 0.022(3) 0.053(4) 0.012(3) 0.018(2) 0.011(2) C8 0.023(4) 0.031(3) 0.068(7) 0.007(2) 0.013(4) 0.011(2) C9 0.076(11) 0.076(11) 0.102(18) 0.000 0.000 0.039(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.056(4) . ? Cu1 N2 2.066(4) . ? Cu1 I1 2.6232(8) . ? Cu1 I2 2.6521(8) . ? Cu1 Cu3 2.822(2) 14_556 ? Cu2 I4 2.512(3) . ? Cu2 I3 2.5130(12) 2_655 ? Cu2 I3 2.5130(12) . ? Cu3 N3 2.04(2) . ? Cu3 I2 2.549(3) 15_556 ? Cu3 I1 2.5893(16) . ? Cu3 I1 2.5893(16) 15_556 ? Cu3 Cu1 2.822(2) 9_556 ? Cu3 Cu1 2.822(2) 15_556 ? I1 Cu3 2.5893(16) 14_556 ? I1 Cu1 2.6232(8) 9_556 ? I2 Cu3 2.549(3) 14_556 ? I2 Cu1 2.6521(8) 20 ? I3 Cu2 2.5130(12) 3_665 ? N1 C1 1.322(6) . ? N1 N1 1.395(8) 20 ? N2 C5 1.334(6) . ? N2 N2 1.389(8) 9_556 ? N3 C9 1.322(17) . ? C1 C2 1.414(6) . ? C1 C3 1.504(7) . ? C2 C2 1.373(14) 20 ? C2 C1 1.414(6) 16_556 ? C3 C4 1.540(7) . ? C4 C3 1.540(7) 16_556 ? C5 C6 1.415(6) . ? C5 C7 1.499(7) . ? C6 C6 1.387(13) 13_566 ? C6 C5 1.415(6) 21_565 ? C7 C8 1.514(9) . ? C8 C7 1.514(8) 21_565 ? C9 N3 1.322(17) 16_556 ? N4 C10 1.08(10) . ? N4 N4 1.42(15) 16_556 ? C10 C11 1.63(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 113.86(16) . . ? N1 Cu1 I1 99.04(12) . . ? N2 Cu1 I1 112.90(12) . . ? N1 Cu1 I2 113.23(12) . . ? N2 Cu1 I2 107.67(12) . . ? I1 Cu1 I2 110.04(3) . . ? N1 Cu1 Cu3 106.12(12) . 14_556 ? N2 Cu1 Cu3 139.96(12) . 14_556 ? I1 Cu1 Cu3 56.65(5) . 14_556 ? I2 Cu1 Cu3 55.40(5) . 14_556 ? I4 Cu2 I3 119.99(5) . 2_655 ? I4 Cu2 I3 119.99(5) . . ? I3 Cu2 I3 120.02(9) 2_655 . ? N3 Cu3 I2 110.1(7) . 15_556 ? N3 Cu3 I1 108.3(4) . . ? I2 Cu3 I1 114.54(6) 15_556 . ? N3 Cu3 I1 108.3(4) . 15_556 ? I2 Cu3 I1 114.54(6) 15_556 15_556 ? I1 Cu3 I1 100.48(8) . 15_556 ? N3 Cu3 Cu1 141.5(3) . 9_556 ? I2 Cu3 Cu1 58.92(5) 15_556 9_556 ? I1 Cu3 Cu1 57.81(4) . 9_556 ? I1 Cu3 Cu1 109.55(8) 15_556 9_556 ? N3 Cu3 Cu1 141.5(3) . 15_556 ? I2 Cu3 Cu1 58.92(5) 15_556 15_556 ? I1 Cu3 Cu1 109.55(8) . 15_556 ? I1 Cu3 Cu1 57.81(4) 15_556 15_556 ? Cu1 Cu3 Cu1 68.70(6) 9_556 15_556 ? Cu3 I1 Cu3 171.48(10) . 14_556 ? Cu3 I1 Cu1 121.95(5) . . ? Cu3 I1 Cu1 65.55(6) 14_556 . ? Cu3 I1 Cu1 65.55(6) . 9_556 ? Cu3 I1 Cu1 121.95(5) 14_556 9_556 ? Cu1 I1 Cu1 78.32(3) . 9_556 ? Cu3 I2 Cu1 65.68(4) 14_556 20 ? Cu3 I2 Cu1 65.68(4) 14_556 . ? Cu1 I2 Cu1 73.79(3) 20 . ? Cu2 I3 Cu2 119.98(9) 3_665 . ? C1 N1 N1 120.2(3) . 20 ? C1 N1 Cu1 123.7(3) . . ? N1 N1 Cu1 115.79(11) 20 . ? C5 N2 N2 120.4(3) . 9_556 ? C5 N2 Cu1 122.0(3) . . ? N2 N2 Cu1 117.43(12) 9_556 . ? C9 N3 Cu3 165(2) . . ? N1 C1 C2 121.1(5) . . ? N1 C1 C3 118.9(4) . . ? C2 C1 C3 119.8(5) . . ? C2 C2 C1 118.6(3) 20 16_556 ? C2 C2 C1 118.6(3) 20 . ? C1 C2 C1 122.6(6) 16_556 . ? C1 C3 C4 110.5(5) . . ? C3 C4 C3 111.5(7) . 16_556 ? N2 C5 C6 121.0(5) . . ? N2 C5 C7 119.2(5) . . ? C6 C5 C7 119.7(5) . . ? C6 C6 C5 118.5(3) 13_566 . ? C6 C6 C5 118.5(3) 13_566 21_565 ? C5 C6 C5 122.9(6) . 21_565 ? C5 C7 C8 111.7(5) . . ? C7 C8 C7 114.5(8) 21_565 . ? N3 C9 N3 158(3) 16_556 . ? C10 N4 N4 180.000(16) . 16_556 ? N4 C10 C11 180.00(2) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 2.262 _refine_diff_density_min -1.027 _refine_diff_density_rms 0.081 #============================================================================== data_c1600 _database_code_depnum_ccdc_archive 'CCDC 227204' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I) Iodide 2:1 Complex with 2,2,7,7-Tetramethyl-1,2,3,6,7,8-Hexahydro-cinnolino[5,4,3-cde]cinnoline, dichloromethane solvate ; _chemical_name_common ; Copper(i) Iodide 2:1 Complex with 2,2,7,7-Tetramethyl- 1,2,3,6,7,8-Hexahydro-cinnolino(5,4,3-cde)cinnoline, dichloromethane solvate ; _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 Cl2 Cu2 I2 N4' _chemical_formula_weight 734.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z' 'x-y, -y, -z' '-x, -x+y, -z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+1/3' 'x-y+2/3, -y+1/3, -z+1/3' '-x+2/3, -x+y+1/3, -z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+2/3' 'x-y+1/3, -y+2/3, -z+2/3' '-x+1/3, -x+y+2/3, -z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z+1/3' '-x+y+2/3, y+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+2/3' '-x+y+1/3, y+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' _cell_length_a 26.1899(14) _cell_length_b 26.1899(14) _cell_length_c 9.6096(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5708.3(7) _cell_formula_units_Z 9 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.922 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3150 _exptl_absorpt_coefficient_mu 4.330 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.4493 _exptl_absorpt_correction_T_max 0.6246 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5412 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 7.34 _diffrn_reflns_theta_max 27.10 _reflns_number_total 1422 _reflns_number_gt 1345 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+120.0994P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1422 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1512 _refine_ls_wR_factor_gt 0.1494 _refine_ls_goodness_of_fit_ref 1.221 _refine_ls_restrained_S_all 1.221 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.01620(5) 0.34953(5) 0.6667 0.0293(3) Uani 1 d S . . I1 I 0.0000 0.26224(3) 0.5000 0.0341(3) Uani 1 d S . . N1 N 0.0845(3) 0.3512(3) 0.7743(5) 0.0255(12) Uani 1 d . . . C1 C 0.1368(3) 0.3689(3) 0.7192(6) 0.0236(13) Uani 1 d . . . C2 C 0.1757(2) 0.3515(4) 0.7760(9) 0.0225(18) Uani 1 d S . . C3 C 0.1558(4) 0.4080(4) 0.5920(7) 0.0368(18) Uani 1 d . . . C5 C 0.2323(4) 0.4645(7) 0.4141(13) 0.055(4) Uani 1 d S . . C4A C 0.2206(5) 0.4411(9) 0.569(2) 0.024(4) Uani 0.50 d SP . . C4B C 0.2041(5) 0.4081(11) 0.5132(19) 0.027(4) Uani 0.50 d SP . . C6B C 0.1752(6) 0.3505(11) 0.431(2) 0.039(5) Uani 0.50 d SP . . C6A C 0.2451(5) 0.4902(10) 0.685(3) 0.044(6) Uani 0.50 d SP . . C7 C 0.2483(8) 0.4965(15) 0.896(4) 0.062(8) Uani 0.50 d SP . . Cl2 Cl 0.2602(9) 0.4714(10) 1.024(2) 0.112(6) Uani 0.25 d P . . Cl1 Cl 0.2791(7) 0.5582(14) 0.819(2) 0.207(11) Uani 0.50 d SP . . 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 0.0348(6) 0.0348(6) 0.0250(5) 0.0027(2) -0.0027(2) 0.0224(6) I1 0.0414(5) 0.0341(3) 0.0291(4) -0.00247(13) -0.0049(3) 0.0207(2) N1 0.025(3) 0.038(3) 0.016(2) 0.004(2) 0.001(2) 0.018(3) C1 0.026(3) 0.024(3) 0.020(3) 0.002(2) 0.002(2) 0.012(3) C2 0.024(3) 0.027(5) 0.017(3) 0.003(4) 0.0017(18) 0.014(2) C3 0.038(4) 0.057(5) 0.029(3) 0.022(3) 0.010(3) 0.034(4) C5 0.054(5) 0.077(10) 0.042(6) 0.041(7) 0.021(3) 0.038(5) C4A 0.025(7) 0.021(10) 0.026(9) -0.001(8) 0.000(4) 0.011(5) C4B 0.029(7) 0.039(13) 0.017(8) 0.018(9) 0.009(5) 0.019(6) C6B 0.045(10) 0.042(13) 0.030(9) -0.002(9) -0.001(4) 0.021(6) C6A 0.045(11) 0.020(10) 0.058(14) 0.003(9) 0.001(5) 0.010(5) C7 0.055(13) 0.07(2) 0.066(18) -0.018(15) -0.009(7) 0.033(10) Cl2 0.123(14) 0.131(15) 0.094(10) 0.018(10) -0.018(9) 0.073(12) Cl1 0.27(2) 0.21(3) 0.121(13) 0.056(15) 0.028(8) 0.107(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.048(6) . ? Cu1 N1 2.048(6) 10_456 ? Cu1 I1 2.6461(9) . ? Cu1 I1 2.6462(9) 9_455 ? I1 Cu1 2.6461(9) 14_554 ? N1 C1 1.318(9) . ? N1 N1 1.394(10) 17_556 ? C1 C2 1.418(8) . ? C1 C3 1.509(9) . ? C2 C2 1.375(17) 31_556 ? C2 C1 1.418(8) 23 ? C3 C4B 1.472(12) . ? C3 C4A 1.486(13) . ? C5 C4A 1.58(2) . ? C5 C4B 1.59(2) . ? C4A C4B 0.92(3) . ? C4A C3 1.486(13) 23 ? C4A C6A 1.58(3) . ? C4B C3 1.472(12) 23 ? C4B C6B 1.53(3) . ? C6B C6B 2.02(4) 31 ? C6A Cl1 2.01(4) . ? C6A C7 2.03(4) . ? C7 Cl2 1.50(4) 23 ? C7 Cl2 1.50(4) . ? C7 Cl1 1.58(5) . ? Cl2 Cl2 1.28(4) 23 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 126.9(3) . 10_456 ? N1 Cu1 I1 94.87(16) . . ? N1 Cu1 I1 111.91(14) 10_456 . ? N1 Cu1 I1 111.91(14) . 9_455 ? N1 Cu1 I1 94.87(16) 10_456 9_455 ? I1 Cu1 I1 118.39(5) . 9_455 ? Cu1 I1 Cu1 76.78(2) 14_554 . ? C1 N1 N1 120.3(4) . 17_556 ? C1 N1 Cu1 123.2(4) . . ? N1 N1 Cu1 113.6(3) 17_556 . ? N1 C1 C2 121.3(6) . . ? N1 C1 C3 119.7(6) . . ? C2 C1 C3 118.9(6) . . ? C2 C2 C1 118.4(4) 31_556 . ? C2 C2 C1 118.4(4) 31_556 23 ? C1 C2 C1 123.2(8) . 23 ? C4B C3 C4A 36.3(10) . . ? C4B C3 C1 114.2(8) . . ? C4A C3 C1 114.2(9) . . ? C4A C5 C4B 33.7(10) . . ? C4B C4A C3 71.0(11) . . ? C4B C4A C3 71.0(11) . 23 ? C3 C4A C3 116.3(14) . 23 ? C4B C4A C5 74.1(17) . . ? C3 C4A C5 108.1(10) . . ? C3 C4A C5 108.1(10) 23 . ? C4B C4A C6A 170(2) . . ? C3 C4A C6A 104.5(11) . . ? C3 C4A C6A 104.5(11) 23 . ? C5 C4A C6A 115.5(17) . . ? C4A C4B C3 72.7(11) . . ? C4A C4B C3 72.7(11) . 23 ? C3 C4B C3 118.0(13) . 23 ? C4A C4B C6B 176(2) . . ? C3 C4B C6B 105.4(12) . . ? C3 C4B C6B 105.4(12) 23 . ? C4A C4B C5 72.2(19) . . ? C3 C4B C5 108.0(10) . . ? C3 C4B C5 108.0(10) 23 . ? C6B C4B C5 112.1(16) . . ? C4B C6B C6B 144(2) . 31 ? C4A C6A Cl1 174.5(18) . . ? C4A C6A C7 139.2(18) . . ? Cl1 C6A C7 46.2(13) . . ? Cl2 C7 Cl2 51(2) 23 . ? Cl2 C7 Cl1 136(2) 23 . ? Cl2 C7 Cl1 136(2) . . ? Cl2 C7 C6A 142.3(18) 23 . ? Cl2 C7 C6A 142.3(18) . . ? Cl1 C7 C6A 66.1(18) . . ? Cl2 Cl2 C7 64.6(10) 23 . ? C7 Cl1 C6A 67.6(18) . . ? _diffrn_measured_fraction_theta_max 0.316 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.316 _refine_diff_density_max 1.751 _refine_diff_density_min -1.490 _refine_diff_density_rms 0.184 #============================================================================== data_c1589 _database_code_depnum_ccdc_archive 'CCDC 227205' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I) Iodide 2:1 Complex with 2,2,7,7-Tetramethyl-1,2,3,6,7,8-Hexahydro-cinnolino[5,4,3-cde]cinnoline, acetonitrile solvate ; _chemical_name_common ; Copper(i) Iodide 2:1 Complex with 2,2,7,7-Tetramethyl- 1,2,3,6,7,8-Hexahydro-cinnolino(5,4,3-cde)cinnoline, acetonitrile solvate ; _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 Cu2 I2 N5' _chemical_formula_weight 690.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 24.063(3) _cell_length_b 13.5575(16) _cell_length_c 6.8122(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2222.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.063 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 4.705 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.2976 _exptl_absorpt_correction_T_max 0.4530 _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 'Siemens SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12648 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.87 _reflns_number_total 2834 _reflns_number_gt 2627 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+2.7100P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00234(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2834 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0583 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.172 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.070869(18) 0.2500 -0.12038(6) 0.02469(11) Uani 1 d S . . Cu2 Cu -0.051450(18) 0.2500 -0.09274(6) 0.02279(10) Uani 1 d S . . I1 I 0.009807(10) 0.2500 0.21843(3) 0.03020(8) Uani 1 d S . . I2 I 0.173341(10) 0.2500 -0.00540(4) 0.03505(9) Uani 1 d S . . N1 N 0.03471(8) 0.13560(14) -0.2863(3) 0.0205(4) Uani 1 d . . . N2 N -0.02247(9) 0.13097(15) -0.2579(3) 0.0223(4) Uani 1 d . . . N3 N -0.13173(13) 0.2500 -0.0315(4) 0.0265(6) Uani 1 d S . . C1 C 0.05896(9) 0.07749(16) -0.4160(3) 0.0198(4) Uani 1 d . . . C2 C 0.02799(9) 0.00431(16) -0.5184(3) 0.0197(4) Uani 1 d . . . C3 C 0.05238(10) -0.06324(17) -0.6520(3) 0.0220(4) Uani 1 d . . . C4 C 0.11362(10) -0.0560(2) -0.6898(4) 0.0325(6) Uani 1 d . . . H4A H 0.1279 -0.1204 -0.7191 0.080 Uiso 1 d R . . H4B H 0.1196 -0.0151 -0.8029 0.080 Uiso 1 d R . . C5 C 0.14583(10) -0.01245(17) -0.5155(4) 0.0240(5) Uani 1 d . . . C6 C 0.11974(10) 0.08706(17) -0.4572(4) 0.0235(5) Uani 1 d . . . H6A H 0.1382 0.1118 -0.3423 0.080 Uiso 1 d R . . H6B H 0.1251 0.1340 -0.5610 0.080 Uiso 1 d R . . C7 C 0.20600(11) 0.0033(2) -0.5803(4) 0.0323(6) Uani 1 d . . . H7A H 0.2227 -0.0584 -0.6167 0.080 Uiso 1 d R . . H7B H 0.2265 0.0331 -0.4752 0.080 Uiso 1 d R . . H7C H 0.2064 0.0479 -0.6897 0.080 Uiso 1 d R . . C8 C 0.14461(13) -0.0836(2) -0.3409(5) 0.0402(7) Uani 1 d . . . H8A H 0.1591 -0.1465 -0.3805 0.080 Uiso 1 d R . . H8B H 0.1071 -0.0914 -0.2955 0.080 Uiso 1 d R . . H8C H 0.1665 -0.0579 -0.2348 0.080 Uiso 1 d R . . C9 C -0.17819(15) 0.2500 -0.0074(5) 0.0255(7) Uani 1 d S . . C10 C -0.23813(17) 0.2500 0.0210(8) 0.0424(10) Uani 1 d S . . H10A H -0.2555 0.2500 -0.1058 0.080 Uiso 1 d SR . . H10B H -0.2494 0.1914 0.0893 0.080 Uiso 1 d 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 0.0227(2) 0.0256(2) 0.0257(2) 0.000 -0.00377(16) 0.000 Cu2 0.0229(2) 0.0243(2) 0.0211(2) 0.000 0.00148(15) 0.000 I1 0.03177(14) 0.04158(15) 0.01726(12) 0.000 -0.00251(8) 0.000 I2 0.02547(13) 0.04902(17) 0.03067(14) 0.000 -0.00950(9) 0.000 N1 0.0184(9) 0.0212(9) 0.0219(9) -0.0026(7) -0.0012(7) -0.0003(7) N2 0.0199(9) 0.0248(9) 0.0223(9) -0.0042(8) 0.0007(8) 0.0006(8) N3 0.0265(15) 0.0255(14) 0.0275(14) 0.000 0.0061(12) 0.000 C1 0.0210(11) 0.0189(10) 0.0195(10) -0.0007(8) -0.0018(8) 0.0020(8) C2 0.0205(11) 0.0193(10) 0.0194(10) -0.0018(8) -0.0003(8) 0.0004(9) C3 0.0197(10) 0.0231(10) 0.0232(11) -0.0037(9) -0.0009(9) 0.0002(9) C4 0.0197(12) 0.0400(14) 0.0379(14) -0.0191(11) 0.0053(10) -0.0025(11) C5 0.0192(10) 0.0219(10) 0.0309(12) -0.0030(9) -0.0006(9) 0.0009(9) C6 0.0198(10) 0.0230(11) 0.0276(11) -0.0046(9) 0.0004(9) -0.0020(9) C7 0.0204(11) 0.0344(14) 0.0420(15) -0.0071(11) 0.0023(10) -0.0012(10) C8 0.0328(14) 0.0371(14) 0.0507(17) 0.0157(13) -0.0032(13) 0.0038(12) C9 0.0299(19) 0.0223(15) 0.0244(17) 0.000 0.0062(14) 0.000 C10 0.026(2) 0.039(2) 0.062(3) 0.000 0.0068(19) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.1071(19) . ? Cu1 N1 2.1071(19) 7_565 ? Cu1 I2 2.5873(6) . ? Cu1 I1 2.7361(6) . ? Cu1 Cu2 2.9494(7) . ? Cu2 N3 1.976(3) . ? Cu2 N2 2.087(2) 7_565 ? Cu2 N2 2.087(2) . ? Cu2 I1 2.5819(5) . ? N1 C1 1.320(3) . ? N1 N2 1.391(3) . ? N2 C3 1.318(3) 5_554 ? N3 C9 1.130(5) . ? C1 C2 1.423(3) . ? C1 C6 1.495(3) . ? C2 C2 1.375(4) 5_554 ? C2 C3 1.418(3) . ? C3 N2 1.318(3) 5_554 ? C3 C4 1.499(3) . ? C4 C5 1.536(3) . ? C5 C7 1.529(3) . ? C5 C8 1.532(4) . ? C5 C6 1.540(3) . ? C9 C10 1.455(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 N1 Cu1 N1 94.80(11) . 7_565 ? N1 Cu1 I2 123.77(5) . . ? N1 Cu1 I2 123.77(5) 7_565 . ? N1 Cu1 I1 103.34(6) . . ? N1 Cu1 I1 103.34(6) 7_565 . ? I2 Cu1 I1 104.859(18) . . ? N1 Cu1 Cu2 67.80(5) . . ? N1 Cu1 Cu2 67.80(5) 7_565 . ? I2 Cu1 Cu2 158.72(2) . . ? I1 Cu1 Cu2 53.857(13) . . ? N3 Cu2 N2 116.13(7) . 7_565 ? N3 Cu2 N2 116.13(7) . . ? N2 Cu2 N2 101.27(11) 7_565 . ? N3 Cu2 I1 112.63(9) . . ? N2 Cu2 I1 104.59(6) 7_565 . ? N2 Cu2 I1 104.59(6) . . ? N3 Cu2 Cu1 171.47(9) . . ? N2 Cu2 Cu1 68.42(6) 7_565 . ? N2 Cu2 Cu1 68.42(6) . . ? I1 Cu2 Cu1 58.846(14) . . ? Cu2 I1 Cu1 67.296(17) . . ? C1 N1 N2 120.22(18) . . ? C1 N1 Cu1 128.02(16) . . ? N2 N1 Cu1 111.54(13) . . ? C3 N2 N1 120.46(19) 5_554 . ? C3 N2 Cu2 127.38(17) 5_554 . ? N1 N2 Cu2 111.74(14) . . ? C9 N3 Cu2 176.2(3) . . ? N1 C1 C2 120.8(2) . . ? N1 C1 C6 120.4(2) . . ? C2 C1 C6 118.7(2) . . ? C2 C2 C3 117.9(3) 5_554 . ? C2 C2 C1 118.9(3) 5_554 . ? C3 C2 C1 123.2(2) . . ? N2 C3 C2 121.5(2) 5_554 . ? N2 C3 C4 120.2(2) 5_554 . ? C2 C3 C4 118.3(2) . . ? C3 C4 C5 112.9(2) . . ? C7 C5 C8 109.3(2) . . ? C7 C5 C4 108.0(2) . . ? C8 C5 C4 110.4(2) . . ? C7 C5 C6 109.79(19) . . ? C8 C5 C6 110.1(2) . . ? C4 C5 C6 109.3(2) . . ? C1 C6 C5 111.79(19) . . ? N3 C9 C10 179.3(4) . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.755 _refine_diff_density_min -0.580 _refine_diff_density_rms 0.089 #============================================================================== data_c1554 _database_code_depnum_ccdc_archive 'CCDC 227206' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I) Bromide 4:1 Complex with 1,2,3,6,7,8-Hexahydro-cinnolino[5,4,3-cde]cinnoline, acetonitrile solvate ; _chemical_name_common ; Copper(i) Bromide 4:1 Complex with 1,2,3,6,7,8-Hexahydro- cinnolino(5,4,3-cde)cinnoline, acetonitrile solvate ; _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Cu4 I4 N6' _chemical_formula_weight 1056.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6797(9) _cell_length_b 7.7125(9) _cell_length_c 11.3151(10) _cell_angle_alpha 104.415(2) _cell_angle_beta 104.170(2) _cell_angle_gamma 96.141(2) _cell_volume 619.20(12) _cell_formula_units_Z 1 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.832 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 8.390 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.2282 _exptl_absorpt_correction_T_max 0.3135 _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3844 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 28.61 _reflns_number_total 2851 _reflns_number_gt 2668 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0974P)^2^+2.0363P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0139(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2851 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.23093(6) 0.95772(6) 0.19035(4) 0.02740(18) Uani 1 d . . . I2 I 0.28927(5) 1.17140(5) 0.57378(4) 0.02449(18) Uani 1 d . . . Cu1 Cu 0.37056(11) 0.70744(11) 0.29034(7) 0.0265(2) Uani 1 d . . . Cu2 Cu 0.48616(11) 1.08553(11) 0.41045(7) 0.0258(2) Uani 1 d . . . N1 N 0.2228(7) 0.6252(6) 0.4031(5) 0.0183(9) Uani 1 d . . . N2 N 0.2925(7) 0.7058(6) 0.5332(5) 0.0192(9) Uani 1 d . . . N3 N 0.3628(8) 0.5016(8) 0.1370(5) 0.0284(11) Uani 1 d . . . C1 C 0.0694(8) 0.5084(7) 0.3560(5) 0.0186(10) Uani 1 d . . . C2 C -0.0325(8) 0.4596(7) 0.4355(5) 0.0178(10) Uani 1 d . . . C3 C -0.1977(8) 0.3328(7) 0.3897(5) 0.0178(10) Uani 1 d . . . C4 C -0.2673(9) 0.2380(10) 0.2499(6) 0.0294(14) Uani 1 d . . . H4A H -0.3979 0.2055 0.2258 0.080 Uiso 1 d R . . H4B H -0.2180 0.1285 0.2309 0.080 Uiso 1 d R . . C5 C -0.2104(8) 0.3629(10) 0.1754(6) 0.0281(14) Uani 1 d . . . H5A H -0.2687 0.4673 0.1893 0.080 Uiso 1 d R . . H5B H -0.2516 0.2995 0.0862 0.080 Uiso 1 d R . . C6 C -0.0040(8) 0.4265(8) 0.2145(5) 0.0226(12) Uani 1 d . . . H6A H 0.0535 0.3248 0.1880 0.080 Uiso 1 d R . . H6B H 0.0247 0.5152 0.1726 0.080 Uiso 1 d R . . C7 C 0.3437(9) 0.3785(9) 0.0518(6) 0.0254(12) Uani 1 d . . . C8 C 0.3181(10) 0.2165(9) -0.0548(7) 0.0331(15) Uani 1 d . . . H8A H 0.3647 0.2432 -0.1209 0.080 Uiso 1 d R . . H8B H 0.1897 0.1677 -0.0846 0.080 Uiso 1 d R . . H8C H 0.3770 0.1286 -0.0209 0.080 Uiso 1 d 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 I1 0.0255(3) 0.0301(3) 0.0225(3) 0.00862(18) 0.00010(17) 0.00027(17) I2 0.0212(2) 0.0259(3) 0.0249(3) 0.00344(17) 0.00696(17) 0.00587(16) Cu1 0.0267(4) 0.0300(4) 0.0216(4) 0.0051(3) 0.0096(3) -0.0006(3) Cu2 0.0235(4) 0.0276(4) 0.0227(4) 0.0055(3) 0.0050(3) -0.0039(3) N1 0.019(2) 0.017(2) 0.017(2) 0.0026(17) 0.0059(18) 0.0005(18) N2 0.019(2) 0.019(2) 0.015(2) 0.0002(17) 0.0025(18) -0.0007(18) N3 0.027(3) 0.031(3) 0.025(3) 0.003(2) 0.011(2) 0.003(2) C1 0.020(2) 0.016(2) 0.018(3) 0.003(2) 0.003(2) 0.004(2) C2 0.017(2) 0.014(2) 0.021(3) 0.004(2) 0.006(2) -0.0006(19) C3 0.017(2) 0.014(2) 0.018(2) 0.0009(19) 0.003(2) -0.0030(19) C4 0.028(3) 0.032(3) 0.017(3) 0.000(2) 0.001(2) -0.012(3) C5 0.018(3) 0.047(4) 0.015(3) 0.006(3) 0.004(2) -0.008(3) C6 0.020(3) 0.024(3) 0.017(3) -0.001(2) 0.006(2) -0.008(2) C7 0.022(3) 0.030(3) 0.026(3) 0.007(2) 0.011(2) 0.002(2) C8 0.038(4) 0.029(3) 0.027(3) 0.000(3) 0.012(3) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Cu2 2.6439(9) . ? I1 Cu1 2.6631(9) . ? I2 Cu1 2.6187(9) 2_676 ? I2 Cu2 2.6671(9) . ? I2 Cu2 2.7730(9) 2_676 ? Cu1 N3 2.023(6) . ? Cu1 N1 2.068(5) . ? Cu1 I2 2.6187(9) 2_676 ? Cu1 Cu2 2.8321(12) . ? Cu2 N2 2.064(5) 2_676 ? Cu2 Cu2 2.6594(16) 2_676 ? Cu2 I2 2.7730(9) 2_676 ? N1 C1 1.308(7) . ? N1 N2 1.389(7) . ? N2 C3 1.332(8) 2_566 ? N2 Cu2 2.064(5) 2_676 ? N3 C7 1.139(9) . ? C1 C2 1.418(8) . ? C1 C6 1.503(8) . ? C2 C2 1.376(11) 2_566 ? C2 C3 1.413(7) . ? C3 N2 1.332(8) 2_566 ? C3 C4 1.499(8) . ? C4 C5 1.524(9) . ? C5 C6 1.527(8) . ? C7 C8 1.462(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cu2 I1 Cu1 64.50(3) . . ? Cu1 I2 Cu2 74.90(3) 2_676 . ? Cu1 I2 Cu2 63.30(3) 2_676 2_676 ? Cu2 I2 Cu2 58.49(3) . 2_676 ? N3 Cu1 N1 112.0(2) . . ? N3 Cu1 I2 108.87(17) . 2_676 ? N1 Cu1 I2 108.83(14) . 2_676 ? N3 Cu1 I1 103.90(18) . . ? N1 Cu1 I1 111.97(14) . . ? I2 Cu1 I1 111.16(3) 2_676 . ? N3 Cu1 Cu2 144.74(17) . . ? N1 Cu1 Cu2 103.02(13) . . ? I2 Cu1 Cu2 61.01(3) 2_676 . ? I1 Cu1 Cu2 57.42(3) . . ? N2 Cu2 I1 129.79(14) 2_676 . ? N2 Cu2 Cu2 108.56(15) 2_676 2_676 ? I1 Cu2 Cu2 121.14(4) . 2_676 ? N2 Cu2 I2 106.52(14) 2_676 . ? I1 Cu2 I2 102.14(3) . . ? Cu2 Cu2 I2 62.74(3) 2_676 . ? N2 Cu2 I2 91.82(14) 2_676 2_676 ? I1 Cu2 I2 107.08(3) . 2_676 ? Cu2 Cu2 I2 58.76(3) 2_676 2_676 ? I2 Cu2 I2 121.51(3) . 2_676 ? N2 Cu2 Cu1 143.10(14) 2_676 . ? I1 Cu2 Cu1 58.08(2) . . ? Cu2 Cu2 Cu1 71.57(4) 2_676 . ? I2 Cu2 Cu1 105.71(3) . . ? I2 Cu2 Cu1 55.69(3) 2_676 . ? C1 N1 N2 121.1(5) . . ? C1 N1 Cu1 122.7(4) . . ? N2 N1 Cu1 116.2(3) . . ? C3 N2 N1 119.0(5) 2_566 . ? C3 N2 Cu2 123.9(4) 2_566 2_676 ? N1 N2 Cu2 116.0(4) . 2_676 ? C7 N3 Cu1 173.7(5) . . ? N1 C1 C2 121.5(5) . . ? N1 C1 C6 119.7(5) . . ? C2 C1 C6 118.8(5) . . ? C2 C2 C3 117.9(6) 2_566 . ? C2 C2 C1 118.4(6) 2_566 . ? C3 C2 C1 123.7(5) . . ? N2 C3 C2 122.1(5) 2_566 . ? N2 C3 C4 119.2(5) 2_566 . ? C2 C3 C4 118.7(5) . . ? C3 C4 C5 109.7(5) . . ? C4 C5 C6 112.2(5) . . ? C1 C6 C5 111.1(5) . . ? N3 C7 C8 178.1(7) . . ? _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 28.61 _diffrn_measured_fraction_theta_full 0.896 _refine_diff_density_max 1.507 _refine_diff_density_min -1.940 _refine_diff_density_rms 0.295 #==============================================================================