#=============================== #Material relevant to the entire paper data_global #=============================== _audit_creation_method SHELXL-97 #==================== # SUMBISSION DETAILS #==================== _publ_contact_author_name 'Robert P. Houser' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of Oklahoma 620 Parrington Oval Norman, OK 73019 USA ; _publ_contact_author_email houser@ou.edu _publ_contact_author_fax '405 325 6111' _publ_contact_author_phone '405 325 3551' #================================= # TITLE AND AUTHOR LIST #================================= _publ_section_title ; Copper(I) Coordination Chemistry of Pyridylmethylamide Ligands ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Yang, Lei' . ; Department of Chemistry and Biochemistry University of Oklahoma 620 Parrington Oval, Room 208 Norman, OK 73019-3051 USA ; 'Houser, Robert P.' . ; Department of Chemistry and Biochemistry University of Oklahoma 620 Parrington Oval, Room 208 Norman, OK 73019-3051 USA ; #========================== #Material relevant to the first compound data_bh4120m_(Complex_1) #========================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 Cl Cu N2 O' _chemical_formula_sum 'C8 H10 Cl Cu N2 O' _chemical_formula_weight 249.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.8153(4) _cell_length_b 13.7892(11) _cell_length_c 14.0641(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 933.84(13) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 5371 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 28.30 _exptl_crystal_description rod _exptl_crystal_colour green _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 2.582 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.292 _exptl_absorpt_correction_T_max 0.511 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10396 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2229 _reflns_number_gt 2219 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2000)' _computing_publication_material 'SHELXTL (Sheldrick, 2000)' _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^)+(0.0335P)^2^+0.1628P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.063(9) _refine_ls_number_reflns 2229 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0180 _refine_ls_R_factor_gt 0.0179 _refine_ls_wR_factor_ref 0.0475 _refine_ls_wR_factor_gt 0.0474 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.12084(4) 0.789658(13) 0.569047(13) 0.01904(6) Uani 1 1 d . . . Cl1 Cl 0.22457(8) 0.64388(3) 0.51133(3) 0.01886(8) Uani 1 1 d . . . O1 O 0.2079(2) 0.67708(9) 0.86960(9) 0.0212(2) Uani 1 1 d . . . N1 N 0.1951(3) 0.87301(9) 0.68114(9) 0.0150(2) Uani 1 1 d . . . N2 N 0.6411(3) 0.71662(9) 0.82397(9) 0.0155(2) Uani 1 1 d . . . H2A H 0.8189 0.7188 0.8383 0.019 Uiso 1 1 calc R . . C1 C 0.0505(3) 0.95597(11) 0.69076(11) 0.0179(3) Uani 1 1 d . . . H1A H -0.0846 0.9716 0.6440 0.021 Uiso 1 1 calc R . . C2 C 0.0897(4) 1.01961(11) 0.76581(11) 0.0190(3) Uani 1 1 d . . . H2B H -0.0209 1.0764 0.7715 0.023 Uiso 1 1 calc R . . C3 C 0.2924(3) 0.99900(12) 0.83198(11) 0.0198(3) Uani 1 1 d . . . H3A H 0.3266 1.0421 0.8834 0.024 Uiso 1 1 calc R . . C4 C 0.4453(3) 0.91448(11) 0.82239(11) 0.0177(3) Uani 1 1 d . . . H4A H 0.5873 0.8994 0.8669 0.021 Uiso 1 1 calc R . . C5 C 0.3895(3) 0.85199(11) 0.74729(10) 0.0143(3) Uani 1 1 d . . . C6 C 0.5429(3) 0.75756(12) 0.73484(11) 0.0173(3) Uani 1 1 d . . . H6A H 0.4183 0.7102 0.7036 0.021 Uiso 1 1 calc R . . H6B H 0.7038 0.7683 0.6923 0.021 Uiso 1 1 calc R . . C7 C 0.4599(3) 0.67544(11) 0.88434(11) 0.0151(3) Uani 1 1 d . . . C8 C 0.5806(3) 0.62787(12) 0.97115(11) 0.0209(3) Uani 1 1 d . . . H8A H 0.4979 0.5635 0.9793 0.031 Uiso 1 1 calc R . . H8B H 0.5405 0.6677 1.0272 0.031 Uiso 1 1 calc R . . H8C H 0.7821 0.6215 0.9635 0.031 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 0.02613(11) 0.01737(10) 0.01362(10) -0.00154(7) -0.00001(7) -0.00024(7) Cl1 0.02316(17) 0.01713(16) 0.01629(17) -0.00145(13) 0.00339(13) -0.00097(12) O1 0.0128(5) 0.0245(6) 0.0264(6) 0.0009(5) -0.0013(4) -0.0003(4) N1 0.0169(6) 0.0153(6) 0.0129(6) 0.0008(4) 0.0002(5) -0.0005(5) N2 0.0109(5) 0.0188(6) 0.0169(6) 0.0012(5) -0.0016(4) 0.0012(5) C1 0.0210(7) 0.0162(7) 0.0164(7) 0.0021(6) -0.0014(6) 0.0004(5) C2 0.0254(8) 0.0127(6) 0.0190(7) 0.0007(5) 0.0023(6) 0.0002(6) C3 0.0271(8) 0.0165(7) 0.0158(7) -0.0015(5) 0.0013(6) -0.0044(6) C4 0.0198(7) 0.0182(7) 0.0150(7) 0.0006(6) -0.0016(6) -0.0018(6) C5 0.0139(6) 0.0151(6) 0.0138(6) 0.0020(5) 0.0020(5) -0.0018(6) C6 0.0186(7) 0.0196(7) 0.0138(7) -0.0003(5) -0.0001(5) 0.0027(6) C7 0.0149(7) 0.0138(6) 0.0166(7) -0.0023(5) 0.0001(5) 0.0020(5) C8 0.0200(7) 0.0246(7) 0.0180(7) 0.0028(6) -0.0017(6) 0.0017(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 Cu1 N1 1.9835(13) . ? Cu1 Cl1 2.2246(4) . ? Cu1 Cl1 2.3997(4) 4_466 ? Cl1 Cu1 2.3997(4) 4_566 ? O1 C7 1.231(2) . ? N1 C1 1.346(2) . ? N1 C5 1.3510(19) . ? N2 C7 1.344(2) . ? N2 C6 1.4538(19) . ? N2 H2A 0.8800 . ? C1 C2 1.386(2) . ? C1 H1A 0.9500 . ? C2 C3 1.378(2) . ? C2 H2B 0.9500 . ? C3 C4 1.385(2) . ? C3 H3A 0.9500 . ? C4 C5 1.389(2) . ? C4 H4A 0.9500 . ? C5 C6 1.507(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.503(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 Cl1 140.63(4) . . ? N1 Cu1 Cl1 107.25(4) . 4_466 ? Cl1 Cu1 Cl1 110.592(14) . 4_466 ? Cu1 Cl1 Cu1 90.309(14) . 4_566 ? C1 N1 C5 118.13(13) . . ? C1 N1 Cu1 118.62(10) . . ? C5 N1 Cu1 123.23(10) . . ? C7 N2 C6 119.83(13) . . ? C7 N2 H2A 120.1 . . ? C6 N2 H2A 120.1 . . ? N1 C1 C2 122.98(14) . . ? N1 C1 H1A 118.5 . . ? C2 C1 H1A 118.5 . . ? C3 C2 C1 118.71(15) . . ? C3 C2 H2B 120.6 . . ? C1 C2 H2B 120.6 . . ? C2 C3 C4 118.96(14) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C3 C4 C5 119.54(14) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? N1 C5 C4 121.63(14) . . ? N1 C5 C6 116.41(13) . . ? C4 C5 C6 121.95(14) . . ? N2 C6 C5 113.25(12) . . ? N2 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? N2 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? O1 C7 N2 121.75(15) . . ? O1 C7 C8 121.74(15) . . ? N2 C7 C8 116.52(13) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 Cl1 Cu1 -90.50(6) . . . 4_566 ? Cl1 Cu1 Cl1 Cu1 106.29(2) 4_466 . . 4_566 ? Cl1 Cu1 N1 C1 -171.32(9) . . . . ? Cl1 Cu1 N1 C1 -7.77(12) 4_466 . . . ? Cl1 Cu1 N1 C5 10.50(15) . . . . ? Cl1 Cu1 N1 C5 174.05(11) 4_466 . . . ? C5 N1 C1 C2 -0.9(2) . . . . ? Cu1 N1 C1 C2 -179.15(12) . . . . ? N1 C1 C2 C3 2.3(2) . . . . ? C1 C2 C3 C4 -1.4(2) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? C1 N1 C5 C4 -1.4(2) . . . . ? Cu1 N1 C5 C4 176.78(11) . . . . ? C1 N1 C5 C6 178.91(13) . . . . ? Cu1 N1 C5 C6 -2.90(18) . . . . ? C3 C4 C5 N1 2.2(2) . . . . ? C3 C4 C5 C6 -178.11(14) . . . . ? C7 N2 C6 C5 73.74(17) . . . . ? N1 C5 C6 N2 -152.04(13) . . . . ? C4 C5 C6 N2 28.3(2) . . . . ? C6 N2 C7 O1 -5.1(2) . . . . ? C6 N2 C7 C8 175.30(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A O1 0.88 2.01 2.8559(17) 161.4 1_655 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.352 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.067 #============================ #Material relevant to the second compound data_bh5050s_(Complex_2) #============================ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H40 Cl2 Cu2 N8 O4' _chemical_formula_sum 'C32 H40 Cl2 Cu2 N8 O4' _chemical_formula_weight 798.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.738(6) _cell_length_b 9.126(4) _cell_length_c 15.083(6) _cell_angle_alpha 90.00 _cell_angle_beta 113.643(7) _cell_angle_gamma 90.00 _cell_volume 1732.3(13) _cell_formula_units_Z 2 _cell_measurement_temperature 87(2) _cell_measurement_reflns_used 8260 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.81 _exptl_crystal_size_mid 0.78 _exptl_crystal_size_min 0.74 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.431 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.390 _exptl_absorpt_correction_T_max 0.417 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 87(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 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18252 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3402 _reflns_number_gt 3361 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2000)' _computing_publication_material 'SHELXTL (Sheldrick, 2000)' _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^)+(0.0360P)^2^+0.9400P] 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 0.0092(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3402 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0617 _refine_ls_wR_factor_gt 0.0615 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.596607(13) 0.451981(18) 0.502967(11) 0.01647(8) Uani 1 1 d . . . Cl1 Cl 0.57317(3) 0.54487(3) 0.64199(2) 0.01665(9) Uani 1 1 d . . . O1 O 0.86331(9) 0.22385(13) 0.48128(8) 0.0297(3) Uani 1 1 d . . . O2 O 0.94719(8) 0.71643(11) 0.73109(7) 0.0204(2) Uani 1 1 d . . . N1 N 0.61689(9) 0.23099(13) 0.53017(8) 0.0159(2) Uani 1 1 d . . . N2 N 0.72510(10) 0.12819(15) 0.35583(9) 0.0229(3) Uani 1 1 d . . . H2N H 0.7046(16) 0.079(2) 0.3089(15) 0.027 Uiso 1 1 d . . . N3 N 0.69981(9) 0.57020(12) 0.46535(8) 0.0146(2) Uani 1 1 d . . . N4 N 0.94828(9) 0.48744(14) 0.67519(8) 0.0158(2) Uani 1 1 d . . . H4N H 0.9787(14) 0.412(2) 0.6877(13) 0.019 Uiso 1 1 d . . . C1 C 0.60436(11) 0.17591(16) 0.60762(10) 0.0201(3) Uani 1 1 d . . . H1 H 0.5884 0.2417 0.6488 0.024 Uiso 1 1 calc R . . C2 C 0.61348(12) 0.02838(17) 0.63044(11) 0.0240(3) Uani 1 1 d . . . H2 H 0.6031 -0.0061 0.6854 0.029 Uiso 1 1 calc R . . C3 C 0.63811(12) -0.06825(16) 0.57166(12) 0.0248(3) Uani 1 1 d . . . H3 H 0.6454 -0.1702 0.5857 0.030 Uiso 1 1 calc R . . C4 C 0.65185(12) -0.01301(17) 0.49218(11) 0.0234(3) Uani 1 1 d . . . H4 H 0.6694 -0.0767 0.4510 0.028 Uiso 1 1 calc R . . C5 C 0.63978(11) 0.13670(15) 0.47274(10) 0.0180(3) Uani 1 1 d . . . C6 C 0.64766(12) 0.20091(17) 0.38352(10) 0.0233(3) Uani 1 1 d . . . H6A H 0.5771 0.1949 0.3290 0.028 Uiso 1 1 calc R . . H6B H 0.6668 0.3058 0.3954 0.028 Uiso 1 1 calc R . . C7 C 0.82982(12) 0.14748(16) 0.40826(10) 0.0223(3) Uani 1 1 d . . . C8 C 0.90280(14) 0.06901(18) 0.37164(12) 0.0282(3) Uani 1 1 d . . . H8A H 0.9477 0.1407 0.3574 0.042 Uiso 1 1 d R . . H8B H 0.8605 0.0148 0.3126 0.042 Uiso 1 1 d R . . H8C H 0.9478 0.0005 0.4211 0.042 Uiso 1 1 d R . . C9 C 0.66632(11) 0.63809(15) 0.37879(10) 0.0190(3) Uani 1 1 d . . . H9 H 0.5921 0.6432 0.3407 0.023 Uiso 1 1 calc R . . C10 C 0.73461(12) 0.70059(15) 0.34279(10) 0.0216(3) Uani 1 1 d . . . H10 H 0.7079 0.7480 0.2816 0.026 Uiso 1 1 calc R . . C11 C 0.84308(12) 0.69244(16) 0.39805(10) 0.0225(3) Uani 1 1 d . . . H11 H 0.8921 0.7324 0.3747 0.027 Uiso 1 1 calc R . . C12 C 0.87888(12) 0.62507(16) 0.48792(10) 0.0193(3) Uani 1 1 d . . . H12 H 0.9527 0.6197 0.5275 0.023 Uiso 1 1 calc R . . C13 C 0.80499(11) 0.56537(14) 0.51930(10) 0.0145(3) Uani 1 1 d . . . C14 C 0.83536(11) 0.48812(16) 0.61507(9) 0.0161(3) Uani 1 1 d . . . H14A H 0.7979 0.5358 0.6514 0.019 Uiso 1 1 calc R . . H14B H 0.8102 0.3855 0.6026 0.019 Uiso 1 1 calc R . . C15 C 0.99533(11) 0.60145(15) 0.73258(9) 0.0165(3) Uani 1 1 d . . . C16 C 1.11069(12) 0.58104(18) 0.79751(12) 0.0259(3) Uani 1 1 d . . . H16A H 1.1235 0.6152 0.8629 0.039 Uiso 1 1 d R . . H16B H 1.1546 0.6377 0.7722 0.039 Uiso 1 1 d R . . H16C H 1.1292 0.4770 0.7998 0.039 Uiso 1 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 0.01570(11) 0.01705(12) 0.01590(11) 0.00166(6) 0.00556(8) -0.00041(6) Cl1 0.01590(17) 0.02002(18) 0.01147(16) -0.00130(11) 0.00280(13) 0.00032(11) O1 0.0329(6) 0.0354(6) 0.0203(5) -0.0094(5) 0.0102(5) -0.0083(5) O2 0.0210(5) 0.0157(5) 0.0231(5) -0.0018(4) 0.0074(4) -0.0005(4) N1 0.0127(5) 0.0169(6) 0.0155(5) 0.0007(4) 0.0030(4) -0.0013(4) N2 0.0285(7) 0.0241(6) 0.0150(6) -0.0075(5) 0.0076(5) -0.0003(5) N3 0.0172(6) 0.0131(5) 0.0130(5) -0.0010(4) 0.0055(4) -0.0004(4) N4 0.0137(6) 0.0150(6) 0.0166(5) 0.0006(5) 0.0038(5) 0.0017(5) C1 0.0161(6) 0.0232(7) 0.0190(6) 0.0021(6) 0.0050(5) -0.0001(5) C2 0.0181(7) 0.0264(8) 0.0246(7) 0.0083(6) 0.0056(6) -0.0018(6) C3 0.0189(7) 0.0170(7) 0.0310(8) 0.0051(6) 0.0022(6) -0.0016(5) C4 0.0208(7) 0.0178(7) 0.0268(8) -0.0031(6) 0.0044(6) -0.0008(6) C5 0.0140(6) 0.0186(7) 0.0174(6) -0.0019(5) 0.0020(5) -0.0016(5) C6 0.0283(8) 0.0225(7) 0.0190(7) -0.0002(6) 0.0093(6) 0.0045(6) C7 0.0303(8) 0.0220(7) 0.0164(6) 0.0014(5) 0.0112(6) -0.0026(6) C8 0.0314(9) 0.0317(8) 0.0253(8) -0.0015(6) 0.0153(7) -0.0010(7) C9 0.0221(7) 0.0177(7) 0.0143(6) 0.0000(5) 0.0043(5) 0.0011(5) C10 0.0336(8) 0.0172(7) 0.0152(6) 0.0019(5) 0.0110(6) 0.0004(6) C11 0.0317(8) 0.0186(7) 0.0236(7) 0.0003(6) 0.0178(6) -0.0029(6) C12 0.0196(7) 0.0191(7) 0.0207(7) -0.0014(5) 0.0096(5) -0.0015(5) C13 0.0180(7) 0.0120(6) 0.0138(6) -0.0024(5) 0.0066(5) -0.0002(5) C14 0.0143(6) 0.0185(7) 0.0140(6) 0.0011(5) 0.0042(5) -0.0020(5) C15 0.0165(6) 0.0182(7) 0.0151(6) 0.0008(5) 0.0068(5) -0.0023(5) C16 0.0171(7) 0.0263(7) 0.0274(8) -0.0028(6) 0.0016(6) -0.0024(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 Cu1 N3 2.0351(13) . ? Cu1 N1 2.0547(15) . ? Cu1 Cl1 2.4001(9) . ? Cu1 Cl1 2.4762(9) 3_666 ? Cu1 Cu1 2.7625(12) 3_666 ? Cl1 Cu1 2.4761(9) 3_666 ? O1 C7 1.2264(18) . ? O2 C15 1.2358(18) . ? N1 C5 1.3446(18) . ? N1 C1 1.3446(19) . ? N2 C7 1.347(2) . ? N2 C6 1.450(2) . ? N2 H2N 0.79(2) . ? N3 C13 1.3449(19) . ? N3 C9 1.3484(18) . ? N4 C15 1.3419(19) . ? N4 C14 1.4493(18) . ? N4 H4N 0.785(19) . ? C1 C2 1.383(2) . ? C1 H1 0.9500 . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C3 C4 1.382(2) . ? C3 H3 0.9500 . ? C4 C5 1.393(2) . ? C4 H4 0.9500 . ? C5 C6 1.511(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.506(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.382(2) . ? C9 H9 0.9500 . ? C10 C11 1.387(2) . ? C10 H10 0.9500 . ? C11 C12 1.386(2) . ? C11 H11 0.9500 . ? C12 C13 1.392(2) . ? C12 H12 0.9500 . ? C13 C14 1.5080(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.504(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 N3 Cu1 N1 121.48(5) . . ? N3 Cu1 Cl1 114.14(4) . . ? N1 Cu1 Cl1 103.13(4) . . ? N3 Cu1 Cl1 105.22(4) . 3_666 ? N1 Cu1 Cl1 101.07(3) . 3_666 ? Cl1 Cu1 Cl1 111.00(3) . 3_666 ? N3 Cu1 Cu1 126.20(4) . 3_666 ? N1 Cu1 Cu1 111.69(3) . 3_666 ? Cl1 Cu1 Cu1 56.801(13) . 3_666 ? Cl1 Cu1 Cu1 54.20(3) 3_666 3_666 ? Cu1 Cl1 Cu1 68.99(3) . 3_666 ? C5 N1 C1 117.70(13) . . ? C5 N1 Cu1 123.20(10) . . ? C1 N1 Cu1 119.08(10) . . ? C7 N2 C6 120.35(13) . . ? C7 N2 H2N 121.0(15) . . ? C6 N2 H2N 118.7(15) . . ? C13 N3 C9 117.87(12) . . ? C13 N3 Cu1 120.90(9) . . ? C9 N3 Cu1 120.54(10) . . ? C15 N4 C14 121.21(12) . . ? C15 N4 H4N 116.7(13) . . ? C14 N4 H4N 119.2(13) . . ? N1 C1 C2 123.35(14) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 118.79(14) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 118.46(14) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C4 C5 119.62(14) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 122.07(13) . . ? N1 C5 C6 116.38(13) . . ? C4 C5 C6 121.51(13) . . ? N2 C6 C5 113.70(12) . . ? N2 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? N2 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? O1 C7 N2 121.96(14) . . ? O1 C7 C8 122.31(15) . . ? N2 C7 C8 115.72(13) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 C10 123.26(13) . . ? N3 C9 H9 118.4 . . ? C10 C9 H9 118.4 . . ? C9 C10 C11 118.47(13) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C12 C11 C10 119.05(13) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 119.01(14) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? N3 C13 C12 122.31(13) . . ? N3 C13 C14 114.35(12) . . ? C12 C13 C14 123.33(13) . . ? N4 C14 C13 114.64(11) . . ? N4 C14 H14A 108.6 . . ? C13 C14 H14A 108.6 . . ? N4 C14 H14B 108.6 . . ? C13 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? O2 C15 N4 122.06(13) . . ? O2 C15 C16 122.25(13) . . ? N4 C15 C16 115.68(13) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 Cl1 Cu1 118.70(4) . . . 3_666 ? N1 Cu1 Cl1 Cu1 -107.50(3) . . . 3_666 ? Cl1 Cu1 Cl1 Cu1 0.0 3_666 . . 3_666 ? N3 Cu1 N1 C5 -46.05(12) . . . . ? Cl1 Cu1 N1 C5 -175.48(10) . . . . ? Cl1 Cu1 N1 C5 69.64(11) 3_666 . . . ? Cu1 Cu1 N1 C5 125.33(10) 3_666 . . . ? N3 Cu1 N1 C1 135.64(10) . . . . ? Cl1 Cu1 N1 C1 6.20(10) . . . . ? Cl1 Cu1 N1 C1 -108.67(10) 3_666 . . . ? Cu1 Cu1 N1 C1 -52.98(10) 3_666 . . . ? N1 Cu1 N3 C13 -52.27(11) . . . . ? Cl1 Cu1 N3 C13 72.22(10) . . . . ? Cl1 Cu1 N3 C13 -165.84(9) 3_666 . . . ? Cu1 Cu1 N3 C13 137.67(9) 3_666 . . . ? N1 Cu1 N3 C9 118.04(10) . . . . ? Cl1 Cu1 N3 C9 -117.47(10) . . . . ? Cl1 Cu1 N3 C9 4.47(11) 3_666 . . . ? Cu1 Cu1 N3 C9 -52.02(11) 3_666 . . . ? C5 N1 C1 C2 -0.2(2) . . . . ? Cu1 N1 C1 C2 178.19(11) . . . . ? N1 C1 C2 C3 0.9(2) . . . . ? C1 C2 C3 C4 -0.4(2) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C1 N1 C5 C4 -0.86(19) . . . . ? Cu1 N1 C5 C4 -179.19(10) . . . . ? C1 N1 C5 C6 176.89(12) . . . . ? Cu1 N1 C5 C6 -1.44(17) . . . . ? C3 C4 C5 N1 1.3(2) . . . . ? C3 C4 C5 C6 -176.36(13) . . . . ? C7 N2 C6 C5 -72.76(18) . . . . ? N1 C5 C6 N2 146.98(13) . . . . ? C4 C5 C6 N2 -35.25(19) . . . . ? C6 N2 C7 O1 1.3(2) . . . . ? C6 N2 C7 C8 -178.84(13) . . . . ? C13 N3 C9 C10 0.9(2) . . . . ? Cu1 N3 C9 C10 -169.69(11) . . . . ? N3 C9 C10 C11 0.4(2) . . . . ? C9 C10 C11 C12 -1.4(2) . . . . ? C10 C11 C12 C13 1.1(2) . . . . ? C9 N3 C13 C12 -1.23(19) . . . . ? Cu1 N3 C13 C12 169.34(10) . . . . ? C9 N3 C13 C14 179.72(12) . . . . ? Cu1 N3 C13 C14 -9.71(15) . . . . ? C11 C12 C13 N3 0.2(2) . . . . ? C11 C12 C13 C14 179.20(13) . . . . ? C15 N4 C14 C13 83.79(16) . . . . ? N3 C13 C14 N4 -177.74(11) . . . . ? C12 C13 C14 N4 3.23(19) . . . . ? C14 N4 C15 O2 -6.1(2) . . . . ? C14 N4 C15 C16 174.84(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N Cl1 0.79(2) 2.69(2) 3.4430(16) 160.7(19) 4_565 N4 H4N O2 0.785(19) 2.176(19) 2.9239(18) 159.5(17) 2_746 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.290 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.058 #============================ #Material relevant to the second compound data_bh5060_(Complex_4) #============================ # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H44 Cl2 Cu2 N4 O2' _chemical_formula_sum 'C52 H44 Cl2 Cu2 N4 O2' _chemical_formula_weight 954.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9143(16) _cell_length_b 9.5821(16) _cell_length_c 13.346(2) _cell_angle_alpha 83.872(5) _cell_angle_beta 80.222(5) _cell_angle_gamma 72.218(5) _cell_volume 1067.9(3) _cell_formula_units_Z 1 _cell_measurement_temperature 87(2) _cell_measurement_reflns_used 5814 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.84 _exptl_crystal_size_mid 0.75 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 1.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.443 _exptl_absorpt_correction_T_max 0.713 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 87(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 'Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11558 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4169 _reflns_number_gt 4041 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2000)' _computing_publication_material 'SHELXTL (Sheldrick, 2000)' _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^)+(0.0480P)^2^+0.9400P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4169 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.39302(3) 0.44456(3) 0.467136(19) 0.02977(10) Uani 1 1 d . . . Cl1 Cl 0.50551(7) 0.37322(6) 0.61226(4) 0.03874(15) Uani 1 1 d . . . N1 N 0.22486(18) 0.38686(16) 0.42104(11) 0.0197(3) Uani 1 1 d . . . C2 C 0.1131(2) 0.4921(2) 0.37733(13) 0.0238(4) Uani 1 1 d . . . H2 H 0.1308 0.5848 0.3583 0.029 Uiso 1 1 calc R . . C3 C -0.0263(2) 0.4715(2) 0.35889(13) 0.0239(4) Uani 1 1 d . . . H3 H -0.1022 0.5486 0.3277 0.029 Uiso 1 1 calc R . . C4 C -0.0538(2) 0.3369(2) 0.38653(14) 0.0240(4) Uani 1 1 d . . . H4 H -0.1494 0.3203 0.3756 0.029 Uiso 1 1 calc R . . C5 C 0.0615(2) 0.22720(19) 0.43050(13) 0.0217(4) Uani 1 1 d . . . H5 H 0.0464 0.1336 0.4499 0.026 Uiso 1 1 calc R . . C6 C 0.1999(2) 0.25542(18) 0.44607(12) 0.0174(3) Uani 1 1 d . . . C7 C 0.3276(2) 0.13789(19) 0.49432(13) 0.0198(3) Uani 1 1 d . . . H7A H 0.3432 0.0427 0.4653 0.024 Uiso 1 1 calc R . . H7B H 0.4293 0.1627 0.4780 0.024 Uiso 1 1 calc R . . N8 N 0.28518(17) 0.12372(15) 0.60502(11) 0.0181(3) Uani 1 1 d . . . H8 H 0.2984 0.1874 0.6431 0.022 Uiso 1 1 calc R . . C9 C 0.22635(19) 0.01497(18) 0.64961(12) 0.0163(3) Uani 1 1 d . . . O10 O 0.21359(16) -0.08024(14) 0.60005(10) 0.0249(3) Uani 1 1 d . . . C11 C 0.17226(19) 0.01231(17) 0.76769(12) 0.0150(3) Uani 1 1 d . . . C12 C 0.01155(19) -0.02242(18) 0.78301(12) 0.0165(3) Uani 1 1 d . . . C13 C -0.1059(2) 0.05706(19) 0.72406(13) 0.0200(3) Uani 1 1 d . . . H13 H -0.0840 0.1290 0.6738 0.024 Uiso 1 1 calc R . . C14 C -0.2533(2) 0.0326(2) 0.73784(14) 0.0235(4) Uani 1 1 d . . . H14 H -0.3319 0.0883 0.6976 0.028 Uiso 1 1 calc R . . C15 C -0.2869(2) -0.0733(2) 0.81045(15) 0.0252(4) Uani 1 1 d . . . H15 H -0.3879 -0.0905 0.8198 0.030 Uiso 1 1 calc R . . C16 C -0.1715(2) -0.1534(2) 0.86887(14) 0.0235(4) Uani 1 1 d . . . H16 H -0.1934 -0.2262 0.9184 0.028 Uiso 1 1 calc R . . C17 C -0.0234(2) -0.12783(19) 0.85549(13) 0.0193(3) Uani 1 1 d . . . H17 H 0.0546 -0.1830 0.8963 0.023 Uiso 1 1 calc R . . C18 C 0.29600(18) -0.11200(18) 0.81933(13) 0.0160(3) Uani 1 1 d . . . C19 C 0.3922(2) -0.23644(19) 0.76957(14) 0.0210(3) Uani 1 1 d . . . H19 H 0.3860 -0.2450 0.7002 0.025 Uiso 1 1 calc R . . C20 C 0.4973(2) -0.3482(2) 0.82091(16) 0.0257(4) Uani 1 1 d . . . H20 H 0.5628 -0.4319 0.7861 0.031 Uiso 1 1 calc R . . C21 C 0.5070(2) -0.3384(2) 0.92213(15) 0.0254(4) Uani 1 1 d . . . H21 H 0.5797 -0.4144 0.9565 0.031 Uiso 1 1 calc R . . C22 C 0.4098(2) -0.2167(2) 0.97302(14) 0.0245(4) Uani 1 1 d . . . H22 H 0.4146 -0.2098 1.0428 0.029 Uiso 1 1 calc R . . C23 C 0.3053(2) -0.10467(19) 0.92190(13) 0.0202(3) Uani 1 1 d . . . H23 H 0.2392 -0.0217 0.9574 0.024 Uiso 1 1 calc R . . C24 C 0.1534(2) 0.16010(18) 0.81215(12) 0.0160(3) Uani 1 1 d . . . C25 C 0.2887(2) 0.20433(19) 0.81461(13) 0.0191(3) Uani 1 1 d . . . H25 H 0.3911 0.1402 0.7926 0.023 Uiso 1 1 calc R . . C26 C 0.2762(2) 0.3399(2) 0.84859(13) 0.0231(4) Uani 1 1 d . . . H26 H 0.3694 0.3685 0.8480 0.028 Uiso 1 1 calc R . . C27 C 0.1281(3) 0.4336(2) 0.88344(14) 0.0266(4) Uani 1 1 d . . . H27 H 0.1190 0.5272 0.9057 0.032 Uiso 1 1 calc R . . C28 C -0.0064(2) 0.3891(2) 0.88549(14) 0.0263(4) Uani 1 1 d . . . H28 H -0.1080 0.4516 0.9111 0.032 Uiso 1 1 calc R . . C29 C 0.0054(2) 0.25400(19) 0.85039(13) 0.0208(3) Uani 1 1 d . . . H29 H -0.0881 0.2252 0.8524 0.025 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 0.02377(14) 0.03382(15) 0.03711(16) -0.00825(11) -0.00259(10) -0.01522(10) Cl1 0.0605(4) 0.0398(3) 0.0291(3) 0.0147(2) -0.0186(2) -0.0333(3) N1 0.0229(7) 0.0211(7) 0.0161(7) 0.0011(5) -0.0029(6) -0.0088(6) C2 0.0320(10) 0.0204(8) 0.0193(8) 0.0028(7) -0.0046(7) -0.0090(7) C3 0.0256(9) 0.0252(9) 0.0182(8) 0.0000(7) -0.0082(7) -0.0014(7) C4 0.0229(9) 0.0283(9) 0.0228(9) -0.0050(7) -0.0078(7) -0.0065(7) C5 0.0260(9) 0.0202(8) 0.0204(8) -0.0025(7) -0.0032(7) -0.0087(7) C6 0.0196(8) 0.0197(8) 0.0125(7) -0.0020(6) -0.0015(6) -0.0052(6) C7 0.0195(8) 0.0223(8) 0.0161(8) 0.0018(6) -0.0014(6) -0.0052(7) N8 0.0219(7) 0.0181(7) 0.0150(7) -0.0003(5) -0.0020(5) -0.0074(6) C9 0.0121(7) 0.0188(8) 0.0164(8) 0.0011(6) -0.0033(6) -0.0023(6) O10 0.0327(7) 0.0277(7) 0.0196(6) -0.0045(5) -0.0021(5) -0.0164(6) C11 0.0133(7) 0.0173(8) 0.0142(7) 0.0011(6) -0.0027(6) -0.0045(6) C12 0.0140(8) 0.0175(8) 0.0181(8) -0.0021(6) -0.0025(6) -0.0046(6) C13 0.0192(8) 0.0205(8) 0.0203(8) 0.0024(6) -0.0048(7) -0.0060(6) C14 0.0158(8) 0.0265(9) 0.0272(9) 0.0000(7) -0.0072(7) -0.0033(7) C15 0.0146(8) 0.0283(9) 0.0339(10) -0.0026(8) -0.0020(7) -0.0088(7) C16 0.0199(9) 0.0229(9) 0.0275(9) 0.0037(7) -0.0005(7) -0.0093(7) C17 0.0173(8) 0.0192(8) 0.0206(8) 0.0014(6) -0.0038(6) -0.0045(6) C18 0.0111(7) 0.0175(8) 0.0200(8) 0.0027(6) -0.0029(6) -0.0059(6) C19 0.0177(8) 0.0217(8) 0.0239(9) -0.0015(7) -0.0032(7) -0.0062(7) C20 0.0183(8) 0.0184(8) 0.0375(10) 0.0002(7) -0.0022(7) -0.0029(7) C21 0.0160(8) 0.0236(9) 0.0344(10) 0.0107(7) -0.0067(7) -0.0049(7) C22 0.0217(9) 0.0297(9) 0.0220(9) 0.0073(7) -0.0070(7) -0.0082(7) C23 0.0176(8) 0.0224(8) 0.0194(8) 0.0017(6) -0.0031(6) -0.0047(7) C24 0.0188(8) 0.0162(8) 0.0123(7) 0.0020(6) -0.0038(6) -0.0044(6) C25 0.0195(8) 0.0218(8) 0.0168(8) 0.0014(6) -0.0059(6) -0.0063(7) C26 0.0310(10) 0.0256(9) 0.0173(8) 0.0018(7) -0.0102(7) -0.0127(7) C27 0.0424(11) 0.0199(9) 0.0180(8) -0.0026(7) -0.0101(8) -0.0064(8) C28 0.0287(10) 0.0247(9) 0.0201(9) -0.0050(7) -0.0039(7) 0.0017(7) C29 0.0193(8) 0.0246(9) 0.0168(8) -0.0001(6) -0.0030(6) -0.0041(7) _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 1.9553(16) . ? Cu1 Cl1 2.2765(6) . ? Cu1 Cl1 2.2878(6) 2_666 ? Cl1 Cu1 2.2878(6) 2_666 ? N1 C6 1.343(2) . ? N1 C2 1.345(2) . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 H4 0.9500 . ? C5 C6 1.393(2) . ? C5 H5 0.9500 . ? C6 C7 1.513(2) . ? C7 N8 1.464(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C9 1.346(2) . ? N8 H8 0.8800 . ? C9 O10 1.225(2) . ? C9 C11 1.568(2) . ? C11 C12 1.543(2) . ? C11 C24 1.545(2) . ? C11 C18 1.546(2) . ? C12 C17 1.391(2) . ? C12 C13 1.400(2) . ? C13 C14 1.383(3) . ? C13 H13 0.9500 . ? C14 C15 1.391(3) . ? C14 H14 0.9500 . ? C15 C16 1.385(3) . ? C15 H15 0.9500 . ? C16 C17 1.394(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.396(2) . ? C18 C19 1.396(2) . ? C19 C20 1.394(3) . ? C19 H19 0.9500 . ? C20 C21 1.383(3) . ? C20 H20 0.9500 . ? C21 C22 1.387(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.398(2) . ? C24 C25 1.402(2) . ? C25 C26 1.387(3) . ? C25 H25 0.9500 . ? C26 C27 1.386(3) . ? C26 H26 0.9500 . ? C27 C28 1.385(3) . ? C27 H27 0.9500 . ? C28 C29 1.391(3) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 Cl1 129.65(5) . . ? N1 Cu1 Cl1 123.95(5) . 2_666 ? Cl1 Cu1 Cl1 106.023(19) . 2_666 ? Cu1 Cl1 Cu1 73.976(19) . 2_666 ? C6 N1 C2 118.00(15) . . ? C6 N1 Cu1 123.26(12) . . ? C2 N1 Cu1 117.72(12) . . ? N1 C2 C3 122.99(17) . . ? N1 C2 H2 118.5 . . ? C3 C2 H2 118.5 . . ? C2 C3 C4 119.12(16) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 118.34(17) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C4 C5 C6 119.40(17) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? N1 C6 C5 122.13(15) . . ? N1 C6 C7 117.29(15) . . ? C5 C6 C7 120.57(15) . . ? N8 C7 C6 111.56(14) . . ? N8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? N8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 N8 C7 121.12(14) . . ? C9 N8 H8 119.4 . . ? C7 N8 H8 119.4 . . ? O10 C9 N8 121.54(15) . . ? O10 C9 C11 119.89(15) . . ? N8 C9 C11 118.57(14) . . ? C12 C11 C24 110.93(13) . . ? C12 C11 C18 109.94(13) . . ? C24 C11 C18 109.70(13) . . ? C12 C11 C9 104.97(13) . . ? C24 C11 C9 112.23(13) . . ? C18 C11 C9 108.97(13) . . ? C17 C12 C13 118.22(15) . . ? C17 C12 C11 122.43(15) . . ? C13 C12 C11 119.33(15) . . ? C14 C13 C12 121.08(16) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 120.20(16) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 119.35(16) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 120.41(17) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C12 C17 C16 120.74(16) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C23 C18 C19 118.26(15) . . ? C23 C18 C11 118.87(15) . . ? C19 C18 C11 122.74(15) . . ? C20 C19 C18 120.47(17) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 120.63(17) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 119.48(16) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C21 C22 C23 120.04(17) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C18 121.12(17) . . ? C22 C23 H23 119.4 . . ? C18 C23 H23 119.4 . . ? C29 C24 C25 117.64(16) . . ? C29 C24 C11 122.78(15) . . ? C25 C24 C11 119.59(14) . . ? C26 C25 C24 121.35(16) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C27 C26 C25 120.22(17) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C28 C27 C26 119.17(17) . . ? C28 C27 H27 120.4 . . ? C26 C27 H27 120.4 . . ? C27 C28 C29 120.78(17) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C28 C29 C24 120.74(17) . . ? C28 C29 H29 119.6 . . ? C24 C29 H29 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 Cl1 Cu1 -173.08(6) . . . 2_666 ? Cl1 Cu1 Cl1 Cu1 0.0 2_666 . . 2_666 ? Cl1 Cu1 N1 C6 -29.45(16) . . . . ? Cl1 Cu1 N1 C6 158.58(11) 2_666 . . . ? Cl1 Cu1 N1 C2 138.77(11) . . . . ? Cl1 Cu1 N1 C2 -33.20(15) 2_666 . . . ? C6 N1 C2 C3 1.1(3) . . . . ? Cu1 N1 C2 C3 -167.72(14) . . . . ? N1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C2 N1 C6 C5 -1.7(2) . . . . ? Cu1 N1 C6 C5 166.53(13) . . . . ? C2 N1 C6 C7 179.47(15) . . . . ? Cu1 N1 C6 C7 -12.3(2) . . . . ? C4 C5 C6 N1 0.9(3) . . . . ? C4 C5 C6 C7 179.75(16) . . . . ? N1 C6 C7 N8 100.32(17) . . . . ? C5 C6 C7 N8 -78.6(2) . . . . ? C6 C7 N8 C9 100.86(18) . . . . ? C7 N8 C9 O10 3.7(2) . . . . ? C7 N8 C9 C11 -175.81(13) . . . . ? O10 C9 C11 C12 -43.64(19) . . . . ? N8 C9 C11 C12 135.91(15) . . . . ? O10 C9 C11 C24 -164.22(15) . . . . ? N8 C9 C11 C24 15.3(2) . . . . ? O10 C9 C11 C18 74.08(18) . . . . ? N8 C9 C11 C18 -106.37(16) . . . . ? C24 C11 C12 C17 -105.48(17) . . . . ? C18 C11 C12 C17 16.0(2) . . . . ? C9 C11 C12 C17 133.09(16) . . . . ? C24 C11 C12 C13 72.80(19) . . . . ? C18 C11 C12 C13 -165.69(15) . . . . ? C9 C11 C12 C13 -48.63(19) . . . . ? C17 C12 C13 C14 0.5(3) . . . . ? C11 C12 C13 C14 -177.83(16) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C13 C12 C17 C16 0.0(3) . . . . ? C11 C12 C17 C16 178.30(16) . . . . ? C15 C16 C17 C12 -0.4(3) . . . . ? C12 C11 C18 C23 -87.56(18) . . . . ? C24 C11 C18 C23 34.7(2) . . . . ? C9 C11 C18 C23 157.90(15) . . . . ? C12 C11 C18 C19 88.22(18) . . . . ? C24 C11 C18 C19 -149.54(15) . . . . ? C9 C11 C18 C19 -26.3(2) . . . . ? C23 C18 C19 C20 -1.5(2) . . . . ? C11 C18 C19 C20 -177.33(15) . . . . ? C18 C19 C20 C21 0.6(3) . . . . ? C19 C20 C21 C22 0.7(3) . . . . ? C20 C21 C22 C23 -1.0(3) . . . . ? C21 C22 C23 C18 0.0(3) . . . . ? C19 C18 C23 C22 1.3(3) . . . . ? C11 C18 C23 C22 177.23(15) . . . . ? C12 C11 C24 C29 -6.4(2) . . . . ? C18 C11 C24 C29 -128.07(16) . . . . ? C9 C11 C24 C29 110.65(17) . . . . ? C12 C11 C24 C25 173.85(14) . . . . ? C18 C11 C24 C25 52.20(19) . . . . ? C9 C11 C24 C25 -69.08(18) . . . . ? C29 C24 C25 C26 -3.4(2) . . . . ? C11 C24 C25 C26 176.32(15) . . . . ? C24 C25 C26 C27 1.6(3) . . . . ? C25 C26 C27 C28 1.1(3) . . . . ? C26 C27 C28 C29 -1.8(3) . . . . ? C27 C28 C29 C24 -0.1(3) . . . . ? C25 C24 C29 C28 2.7(2) . . . . ? C11 C24 C29 C28 -177.08(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8 Cl1 0.88 2.89 3.5445(16) 132.7 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.381 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.057 #========================== #Material relevant to the first compound data_bh5106n_(Complex_5) #========================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H32 Cl Cu N4 O2' _chemical_formula_sum 'C22 H32 Cl Cu N4 O2' _chemical_formula_weight 483.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.162(3) _cell_length_b 7.3381(16) _cell_length_c 15.441(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.754(5) _cell_angle_gamma 90.00 _cell_volume 1204.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6217 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 28.34 _exptl_crystal_description prism _exptl_crystal_colour light _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 1.042 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6929 _exptl_absorpt_correction_T_max 0.8679 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Bruker APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9069 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0157 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2359 _reflns_number_gt 2271 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2000)' _computing_publication_material 'SHELXTL (Sheldrick, 2000)' _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^)+(0.0400P)^2^+1.3000P] 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 2359 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0791 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.0000 0.60709(4) 0.2500 0.01963(11) Uani 1 2 d S . . Cl1 Cl 0.0000 0.92134(9) 0.2500 0.0531(3) Uani 1 2 d S . . N1 N 0.17508(13) 0.5274(2) 0.28969(9) 0.0176(3) Uani 1 1 d . . . C2 C 0.25424(18) 0.6138(2) 0.36172(12) 0.0222(4) Uani 1 1 d . . . H2 H 0.2217 0.7078 0.3904 0.027 Uiso 1 1 calc R . . C3 C 0.38027(18) 0.5714(3) 0.39550(12) 0.0251(4) Uani 1 1 d . . . H3 H 0.4333 0.6356 0.4462 0.030 Uiso 1 1 calc R . . C4 C 0.42835(17) 0.4339(3) 0.35432(12) 0.0237(4) Uani 1 1 d . . . H4 H 0.5148 0.4017 0.3763 0.028 Uiso 1 1 calc R . . C5 C 0.34776(16) 0.3441(3) 0.28044(12) 0.0203(4) Uani 1 1 d . . . H5 H 0.3784 0.2489 0.2512 0.024 Uiso 1 1 calc R . . C6 C 0.22200(16) 0.3942(2) 0.24936(11) 0.0168(3) Uani 1 1 d . . . C7 C 0.12947(16) 0.3091(3) 0.16674(12) 0.0223(4) Uani 1 1 d . . . H7A H 0.0464 0.3016 0.1772 0.027 Uiso 1 1 calc R . . H7B H 0.1204 0.3904 0.1139 0.027 Uiso 1 1 calc R . . N8 N 0.16371(15) 0.1294(2) 0.14410(11) 0.0215(3) Uani 1 1 d . . . H8 H 0.136(2) 0.046(3) 0.1638(15) 0.026 Uiso 1 1 d . . . C9 C 0.23283(18) 0.1038(2) 0.08706(12) 0.0221(4) Uani 1 1 d . . . O10 O 0.27838(14) 0.23280(19) 0.05739(9) 0.0295(3) Uani 1 1 d . . . C11 C 0.2539(2) -0.0953(3) 0.06476(13) 0.0264(4) Uani 1 1 d . . . C12 C 0.3441(3) -0.1824(4) 0.14905(17) 0.0482(6) Uani 1 1 d . . . H12A H 0.3579 -0.3101 0.1363 0.072 Uiso 1 1 d R . . H12B H 0.3079 -0.1760 0.1994 0.072 Uiso 1 1 d R . . H12C H 0.4245 -0.1170 0.1658 0.072 Uiso 1 1 d R . . C13 C 0.1310(3) -0.2046(4) 0.0409(3) 0.0675(10) Uani 1 1 d . . . H13A H 0.1473 -0.3307 0.0267 0.101 Uiso 1 1 d R . . H13B H 0.0694 -0.1497 -0.0121 0.101 Uiso 1 1 d R . . H13C H 0.0976 -0.2034 0.0927 0.101 Uiso 1 1 d R . . C14 C 0.3094(4) -0.1008(4) -0.0131(2) 0.0802(13) Uani 1 1 d . . . H14A H 0.3853 -0.0252 0.0018 0.120 Uiso 1 1 d R . . H14B H 0.2477 -0.0540 -0.0683 0.120 Uiso 1 1 d R . . H14C H 0.3311 -0.2267 -0.0232 0.120 Uiso 1 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 0.01821(17) 0.01584(17) 0.02864(19) 0.000 0.01280(13) 0.000 Cl1 0.0434(5) 0.0139(3) 0.1242(9) 0.000 0.0587(5) 0.000 N1 0.0186(7) 0.0165(7) 0.0198(7) -0.0016(6) 0.0091(5) -0.0028(6) C2 0.0296(10) 0.0194(9) 0.0185(8) -0.0034(7) 0.0087(7) -0.0044(7) C3 0.0274(9) 0.0272(9) 0.0173(8) -0.0005(7) 0.0015(7) -0.0090(8) C4 0.0178(8) 0.0315(10) 0.0208(8) 0.0053(7) 0.0042(7) -0.0041(7) C5 0.0176(8) 0.0253(9) 0.0199(8) 0.0007(7) 0.0083(6) 0.0007(7) C6 0.0172(8) 0.0177(8) 0.0174(8) -0.0006(6) 0.0080(6) -0.0024(6) C7 0.0179(8) 0.0206(9) 0.0257(9) -0.0079(7) 0.0026(7) 0.0019(7) N8 0.0240(8) 0.0175(7) 0.0235(8) -0.0048(6) 0.0080(6) 0.0009(6) C9 0.0256(9) 0.0240(10) 0.0141(8) -0.0007(7) 0.0022(7) 0.0069(7) O10 0.0410(8) 0.0276(7) 0.0223(6) 0.0026(5) 0.0133(6) 0.0043(6) C11 0.0338(11) 0.0244(10) 0.0203(9) -0.0021(7) 0.0071(8) 0.0119(8) C12 0.0555(15) 0.0410(13) 0.0399(13) 0.0032(11) 0.0024(11) 0.0262(12) C13 0.0407(14) 0.0412(14) 0.106(2) -0.0482(16) -0.0003(15) 0.0056(12) C14 0.171(4) 0.0382(15) 0.0640(19) 0.0073(13) 0.085(2) 0.0331(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.9509(15) . ? Cu1 N1 1.9509(15) 2 ? Cu1 Cl1 2.3060(9) . ? N1 C6 1.348(2) . ? N1 C2 1.349(2) . ? C2 C3 1.378(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(3) . ? C4 H4 0.9500 . ? C5 C6 1.387(2) . ? C5 H5 0.9500 . ? C6 C7 1.510(2) . ? C7 N8 1.445(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C9 1.349(2) . ? N8 H8 0.79(2) . ? C9 O10 1.228(2) . ? C9 C11 1.535(2) . ? C11 C14 1.511(3) . ? C11 C12 1.522(3) . ? C11 C13 1.535(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 145.12(9) . 2 ? N1 Cu1 Cl1 107.44(4) . . ? N1 Cu1 Cl1 107.44(4) 2 . ? C6 N1 C2 118.20(15) . . ? C6 N1 Cu1 124.43(12) . . ? C2 N1 Cu1 117.37(12) . . ? N1 C2 C3 122.85(17) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C2 C3 C4 118.94(16) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 118.64(17) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 119.58(17) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N1 C6 C5 121.79(15) . . ? N1 C6 C7 115.35(15) . . ? C5 C6 C7 122.83(15) . . ? N8 C7 C6 114.73(14) . . ? N8 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? N8 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C9 N8 C7 122.08(16) . . ? C9 N8 H8 121.0(17) . . ? C7 N8 H8 116.8(17) . . ? O10 C9 N8 121.35(17) . . ? O10 C9 C11 122.74(17) . . ? N8 C9 C11 115.88(17) . . ? C14 C11 C12 110.2(2) . . ? C14 C11 C13 110.4(2) . . ? C12 C11 C13 107.2(2) . . ? C14 C11 C9 109.38(18) . . ? C12 C11 C9 108.32(16) . . ? C13 C11 C9 111.35(17) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 N1 C6 45.05(12) 2 . . . ? Cl1 Cu1 N1 C6 -134.95(12) . . . . ? N1 Cu1 N1 C2 -135.81(13) 2 . . . ? Cl1 Cu1 N1 C2 44.19(13) . . . . ? C6 N1 C2 C3 0.0(3) . . . . ? Cu1 N1 C2 C3 -179.22(14) . . . . ? N1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C2 N1 C6 C5 0.5(2) . . . . ? Cu1 N1 C6 C5 179.62(12) . . . . ? C2 N1 C6 C7 -177.44(15) . . . . ? Cu1 N1 C6 C7 1.7(2) . . . . ? C4 C5 C6 N1 -0.6(3) . . . . ? C4 C5 C6 C7 177.13(17) . . . . ? N1 C6 C7 N8 -158.39(15) . . . . ? C5 C6 C7 N8 23.7(2) . . . . ? C6 C7 N8 C9 -90.5(2) . . . . ? C7 N8 C9 O10 5.9(3) . . . . ? C7 N8 C9 C11 -176.05(15) . . . . ? O10 C9 C11 C14 -13.2(3) . . . . ? N8 C9 C11 C14 168.8(2) . . . . ? O10 C9 C11 C12 106.9(2) . . . . ? N8 C9 C11 C12 -71.1(2) . . . . ? O10 C9 C11 C13 -135.5(2) . . . . ? N8 C9 C11 C13 46.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8 Cl1 0.79(2) 2.48(2) 3.1884(18) 151(2) 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.570 _refine_diff_density_min -0.759 _refine_diff_density_rms 0.054 #===END