Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Cai, Jiwen' 'Chen, Cai-Hong' 'Chen, Xiao-Ming' 'Liao, Cheng-Zhu' 'Yao, Jun-Hua' _publ_contact_author_name 'Dr Jiwen Cai' _publ_contact_author_address ; Dr Jiwen Cai Instrumentation Analysis & Research Center Zhongshan University Guangzhou 510275 CHINA ; data_compound 1 _database_code_ 145435 _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(ethylenediamine)-copper(II) naphthalene-1,5-disulfonate dihydrate ; _chemical_name_common Cu(en)2(1,5nds).2H2O _chemical_melting_point ? _chemical_formula_moiety Cu1 C4 H16 N4 2+, C10 H6 S2 O6 2-, 2(H2 O1) _chemical_formula_sum 'C14 H26 Cu N4 O8 S2' _chemical_formula_weight 506.05 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' 'S' 'S' 0.1246 0.1234 '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 Tetragonal _symmetry_space_group_name_H-M P4(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 9.4371(9) _cell_length_b 9.4371(9) _cell_length_c 22.129(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1970.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.03 _exptl_crystal_description block _exptl_crystal_colour purple-brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1052 _exptl_absorpt_coefficient_mu 1.372 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.7710 _exptl_absorpt_correction_T_max 0.8527 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18533 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0093 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.03 _reflns_number_total 2146 _reflns_number_gt 2096 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0347P)^2^+0.4371P] 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 0.007(11) _refine_ls_number_reflns 2146 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0201 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0547 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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 Cu Cu 0.22735(2) 0.22735(2) 0.0000 0.03305(9) Uani 1 2 d S . . OW O 0.27948(17) 0.79298(16) 0.07450(7) 0.0548(4) Uani 1 1 d . . . HW1 H 0.2387 0.7512 0.0520 0.075(10) Uiso 1 1 d R . . HW2 H 0.3302 0.8389 0.0509 0.085(10) Uiso 1 1 d R . . N1 N 0.37100(17) 0.30411(18) 0.05710(7) 0.0406(4) Uani 1 1 d . . . H1A H 0.3304 0.3195 0.0933 0.049 Uiso 1 1 calc R . . H1B H 0.4409 0.2403 0.0621 0.049 Uiso 1 1 calc R . . N2 N 0.13002(18) 0.10509(17) 0.06090(7) 0.0391(3) Uani 1 1 d . . . H2A H 0.1893 0.0369 0.0738 0.047 Uiso 1 1 calc R . . H2B H 0.1035 0.1575 0.0930 0.047 Uiso 1 1 calc R . . C6 C 0.4306(2) 0.4373(2) 0.03401(9) 0.0451(4) Uani 1 1 d . . . H6A H 0.5249 0.4516 0.0504 0.054 Uiso 1 1 calc R . . H6B H 0.3717 0.5164 0.0464 0.054 Uiso 1 1 calc R . . C9 C 0.0043(2) 0.0407(2) 0.03217(9) 0.0470(5) Uani 1 1 d . . . H9A H -0.0745 0.1067 0.0331 0.056 Uiso 1 1 calc R . . H9B H -0.0233 -0.0442 0.0539 0.056 Uiso 1 1 calc R . . O1 O 0.39773(12) -0.01504(15) -0.01386(6) 0.0380(3) Uani 1 1 d . . . S1 S 0.53248(4) 0.02571(4) -0.040825(17) 0.02389(9) Uani 1 1 d . . . O2 O 0.51789(15) 0.08208(13) -0.10123(5) 0.0372(3) Uani 1 1 d . . . O3 O 0.61222(12) 0.11993(11) -0.00093(6) 0.0305(2) Uani 1 1 d . . . C1 C 0.67475(17) -0.17334(17) -0.10477(7) 0.0268(3) Uani 1 1 d . . . H1CA H 0.6345 -0.1293 -0.1382 0.032 Uiso 1 1 calc R . . C2 C 0.63947(15) -0.12967(16) -0.04768(7) 0.0230(3) Uani 1 1 d . . . C3 C 0.69590(14) -0.19783(14) 0.00442(7) 0.0213(3) Uani 1 1 d . . . C4 C 0.65324(16) -0.16393(16) 0.06447(7) 0.0248(3) Uani 1 1 d . . . H4AA H 0.5823 -0.0971 0.0707 0.030 Uiso 1 1 calc R . . C5 C 0.71489(17) -0.22789(17) 0.11277(7) 0.0291(3) Uani 1 1 d . . . H5AA H 0.6830 -0.2072 0.1515 0.035 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 Cu 0.03627(11) 0.03627(11) 0.02662(14) 0.00041(9) -0.00041(9) -0.00398(12) OW 0.0657(10) 0.0533(9) 0.0453(8) -0.0048(7) 0.0012(7) -0.0284(8) N1 0.0413(8) 0.0449(9) 0.0357(8) -0.0015(6) -0.0039(7) 0.0016(7) N2 0.0459(9) 0.0367(8) 0.0346(7) 0.0013(6) 0.0062(7) 0.0037(7) C6 0.0405(10) 0.0407(11) 0.0542(11) -0.0065(9) -0.0038(9) -0.0011(8) C9 0.0404(10) 0.0442(11) 0.0563(11) 0.0005(9) 0.0112(9) -0.0057(8) O1 0.0231(5) 0.0389(7) 0.0521(8) -0.0012(6) 0.0035(5) 0.0037(5) S1 0.02363(17) 0.02257(17) 0.02548(17) -0.00040(14) -0.00351(14) 0.00402(13) O2 0.0489(7) 0.0332(6) 0.0294(6) 0.0036(5) -0.0133(5) 0.0098(6) O3 0.0383(6) 0.0257(5) 0.0275(5) -0.0034(5) -0.0052(5) -0.0003(4) C1 0.0287(7) 0.0317(8) 0.0199(6) 0.0009(6) -0.0037(6) 0.0036(6) C2 0.0219(7) 0.0235(7) 0.0236(7) -0.0012(6) -0.0004(6) 0.0018(5) C3 0.0207(7) 0.0219(7) 0.0214(6) -0.0010(5) -0.0005(5) 0.0008(5) C4 0.0257(7) 0.0252(7) 0.0236(7) -0.0017(6) 0.0044(6) 0.0039(6) C5 0.0353(8) 0.0331(8) 0.0188(6) -0.0005(6) 0.0062(6) 0.0046(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 Cu N1 1.9897(16) . ? Cu N1 1.9897(16) 7 ? Cu N2 1.9978(15) 7 ? Cu N2 1.9978(15) . ? Cu O1 2.8128(13) . ? N1 C6 1.469(3) . ? N2 C9 1.477(3) . ? C6 C6 1.508(4) 7 ? C9 C9 1.504(4) 7 ? O1 S1 1.4564(12) . ? S1 O2 1.4453(12) . ? S1 O3 1.4616(12) . ? S1 C2 1.7868(15) . ? C1 C2 1.370(2) . ? C1 C5 1.410(2) 7_645 ? C2 C3 1.424(2) . ? C3 C4 1.425(2) . ? C3 C3 1.432(3) 7_645 ? C4 C5 1.358(2) . ? C5 C1 1.410(2) 7_645 ? 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 Cu N1 84.67(10) . 7 ? N1 Cu N2 171.59(7) . 7 ? N1 Cu N2 95.46(7) 7 7 ? N1 Cu N2 95.46(7) . . ? N1 Cu N2 171.59(7) 7 . ? N2 Cu N2 85.65(9) 7 . ? N1 Cu O1 88.62(5) . . ? N1 Cu O1 106.06(5) 7 . ? N2 Cu O1 83.26(6) 7 . ? N2 Cu O1 82.34(5) . . ? C6 N1 Cu 110.58(12) . . ? C9 N2 Cu 108.46(11) . . ? N1 C6 C6 109.10(12) . 7 ? N2 C9 C9 108.54(13) . 7 ? S1 O1 Cu 109.21(7) . . ? O2 S1 O1 113.14(8) . . ? O2 S1 O3 112.56(8) . . ? O1 S1 O3 111.27(8) . . ? O2 S1 C2 106.10(7) . . ? O1 S1 C2 108.15(7) . . ? O3 S1 C2 105.05(7) . . ? C2 C1 C5 119.95(14) . 7_645 ? C1 C2 C3 121.33(14) . . ? C1 C2 S1 117.55(11) . . ? C3 C2 S1 120.89(11) . . ? C2 C3 C4 123.24(13) . . ? C2 C3 C3 117.89(17) . 7_645 ? C4 C3 C3 118.86(16) . 7_645 ? C5 C4 C3 120.86(13) . . ? C4 C5 C1 120.74(14) . 7_645 ? 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 Cu N1 C6 12.30(10) 7 . . . ? N2 Cu N1 C6 103.6(5) 7 . . . ? N2 Cu N1 C6 -159.25(13) . . . . ? O1 Cu N1 C6 118.58(13) . . . . ? N1 Cu N2 C9 174.82(12) . . . . ? N1 Cu N2 C9 84.3(5) 7 . . . ? N2 Cu N2 C9 -13.55(9) 7 . . . ? O1 Cu N2 C9 -97.32(13) . . . . ? Cu N1 C6 C6 -33.7(3) . . . 7 ? Cu N2 C9 C9 37.6(2) . . . 7 ? N1 Cu O1 S1 -63.39(8) . . . . ? N1 Cu O1 S1 20.67(9) 7 . . . ? N2 Cu O1 S1 114.43(8) 7 . . . ? N2 Cu O1 S1 -159.08(9) . . . . ? Cu O1 S1 O2 -63.88(8) . . . . ? Cu O1 S1 O3 64.01(8) . . . . ? Cu O1 S1 C2 178.89(6) . . . . ? C5 C1 C2 C3 -2.0(2) 7_645 . . . ? C5 C1 C2 S1 172.64(13) 7_645 . . . ? O2 S1 C2 C1 -5.88(15) . . . . ? O1 S1 C2 C1 115.79(13) . . . . ? O3 S1 C2 C1 -125.30(13) . . . . ? O2 S1 C2 C3 168.74(12) . . . . ? O1 S1 C2 C3 -69.59(14) . . . . ? O3 S1 C2 C3 49.32(14) . . . . ? C1 C2 C3 C4 -174.58(15) . . . . ? S1 C2 C3 C4 11.0(2) . . . . ? C1 C2 C3 C3 6.34(17) . . . 7_645 ? S1 C2 C3 C3 -168.08(6) . . . 7_645 ? C2 C3 C4 C5 -177.12(15) . . . . ? C3 C3 C4 C5 1.94(19) 7_645 . . . ? C3 C4 C5 C1 2.6(3) . . . 7_645 ? 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 OW HW1 O3 0.74 2.06 2.7977(19) 170.6 7 OW HW2 O1 0.83 2.09 2.890(2) 162.1 1_565 N1 H1A OW 0.90 2.11 2.982(2) 163.4 5_545 N1 H1B O3 0.90 2.42 3.139(2) 137.2 . N2 H2A OW 0.90 2.45 3.280(2) 152.7 1_545 N2 H2B OW 0.90 2.49 3.210(2) 137.5 5_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.190 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.054 #==========================================END data_compound2 _database_code_ 145436 _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(N-methylethylenediamine)-copper(II) naphthalene-2,6-disulfonate dihydrate ; _chemical_name_common Cu(Men)2(2,6nds).2H2O _chemical_melting_point ? _chemical_formula_moiety Cu1 C6 H20 N4 2+, C10 H6 S2 O6 2-, 2(H2 O1) _chemical_formula_sum 'C16 H30 Cu N4 O8 S2' _chemical_formula_weight 534.10 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.390(9) _cell_length_b 9.631(10) _cell_length_c 14.001(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00(2) _cell_angle_gamma 90.00 _cell_volume 1131(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.23 _cell_measurement_theta_max 30.31 _exptl_crystal_description column _exptl_crystal_colour blue _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 558 _exptl_absorpt_coefficient_mu 1.199 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.8313 _exptl_absorpt_correction_T_max 0.9101 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7791 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 30.31 _reflns_number_total 3241 _reflns_number_gt 2519 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.1119P] 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 3241 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Cu Cu 0.0000 0.5000 0.5000 0.03064(10) Uani 1 2 d S . . S1 S 0.36219(4) 0.62909(4) 0.64548(3) 0.02489(10) Uani 1 1 d . . . O2 O 0.28775(16) 0.68925(14) 0.73037(9) 0.0413(3) Uani 1 1 d . . . O1 O 0.25253(15) 0.55024(15) 0.58767(10) 0.0419(3) Uani 1 1 d . . . O3 O 0.50578(14) 0.55107(14) 0.66579(9) 0.0382(3) Uani 1 1 d . . . N1 N 0.13601(17) 0.41496(17) 0.39544(10) 0.0358(3) Uani 1 1 d . . . H1A H 0.2386 0.4122 0.4140 0.043 Uiso 1 1 calc R . . H1B H 0.1036 0.3276 0.3836 0.043 Uiso 1 1 calc R . . N2 N -0.00038(18) 0.32737(16) 0.58785(10) 0.0355(3) Uani 1 1 d . . . H2C H 0.0939 0.3306 0.6199 0.043 Uiso 1 1 calc R . . C1 C -0.0097(3) 0.1856(2) 0.54788(17) 0.0540(6) Uani 1 1 d . . . H1C H -0.0079 0.1191 0.5990 0.081 Uiso 1 1 calc R . . H1D H 0.0795 0.1699 0.5064 0.081 Uiso 1 1 calc R . . H1E H -0.1069 0.1757 0.5124 0.081 Uiso 1 1 calc R . . C2 C -0.1258(2) 0.3505(2) 0.66206(14) 0.0437(5) Uani 1 1 d . . . H2A H -0.1062 0.2913 0.7169 0.052 Uiso 1 1 calc R . . H2B H -0.2300 0.3280 0.6363 0.052 Uiso 1 1 calc R . . C3 C 0.1203(2) 0.5000(2) 0.30870(14) 0.0426(5) Uani 1 1 d . . . H3A H 0.0201 0.4799 0.2770 0.051 Uiso 1 1 calc R . . H3B H 0.2066 0.4797 0.2648 0.051 Uiso 1 1 calc R . . C4 C 0.5684(2) 0.84373(16) 0.43158(11) 0.0286(3) Uani 1 1 d . . . H4A H 0.6238 0.8228 0.3759 0.034 Uiso 1 1 calc R . . C5 C 0.51238(19) 0.73790(18) 0.48772(11) 0.0291(3) Uani 1 1 d . . . H5A H 0.5291 0.6460 0.4701 0.035 Uiso 1 1 calc R . . C6 C 0.42809(18) 0.76990(16) 0.57358(10) 0.0228(3) Uani 1 1 d . . . C7 C 0.39938(18) 0.90370(17) 0.60027(10) 0.0249(3) Uani 1 1 d . . . H7A H 0.3423 0.9220 0.6558 0.030 Uiso 1 1 calc R . . C8 C 0.45670(19) 1.01582(15) 0.54319(11) 0.0235(3) Uani 1 1 d . . . OW O 0.50666(19) 0.33518(17) 0.80297(11) 0.0607(4) Uani 1 1 d . . . HW1 H 0.5111 0.4015 0.7605 0.072(8) Uiso 1 1 d R . . HW2 H 0.4162 0.2874 0.7917 0.088(10) 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 Cu 0.03414(17) 0.02608(16) 0.03170(17) 0.00042(11) -0.00013(12) -0.00250(11) S1 0.02442(19) 0.02322(18) 0.02702(19) 0.00466(15) 0.00166(14) -0.00274(14) O2 0.0523(8) 0.0398(7) 0.0318(6) 0.0063(5) 0.0171(6) 0.0006(6) O1 0.0375(7) 0.0392(7) 0.0491(8) 0.0031(6) -0.0089(6) -0.0158(6) O3 0.0317(7) 0.0361(7) 0.0467(7) 0.0164(6) -0.0006(5) 0.0038(5) N1 0.0307(8) 0.0387(8) 0.0381(8) -0.0014(7) -0.0039(6) -0.0002(6) N2 0.0338(8) 0.0346(8) 0.0380(8) 0.0037(6) -0.0087(6) -0.0035(6) C1 0.0732(15) 0.0327(10) 0.0562(13) 0.0017(10) -0.0149(11) -0.0037(10) C2 0.0382(10) 0.0529(12) 0.0402(10) 0.0139(9) -0.0025(8) -0.0060(9) C3 0.0365(10) 0.0597(13) 0.0316(9) 0.0010(9) -0.0003(7) 0.0001(9) C4 0.0384(9) 0.0242(8) 0.0231(7) -0.0034(6) 0.0093(6) 0.0023(7) C5 0.0368(9) 0.0238(8) 0.0268(8) -0.0027(6) 0.0053(6) 0.0003(6) C6 0.0246(7) 0.0231(7) 0.0208(7) 0.0017(6) 0.0004(5) -0.0018(6) C7 0.0280(8) 0.0272(8) 0.0195(7) 0.0002(6) 0.0043(6) -0.0012(6) C8 0.0278(8) 0.0226(7) 0.0202(7) 0.0003(6) 0.0035(6) 0.0006(6) OW 0.0587(10) 0.0589(10) 0.0645(10) 0.0322(8) -0.0116(8) -0.0084(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 2.029(2) . ? Cu N1 2.029(2) 3_566 ? Cu N2 2.068(2) . ? Cu N2 2.068(2) 3_566 ? Cu O1 2.496(2) . ? S1 O1 1.4417(16) . ? S1 O3 1.4481(17) . ? S1 O2 1.4623(17) . ? S1 C6 1.777(2) . ? N1 C3 1.471(3) . ? N2 C1 1.478(3) . ? N2 C2 1.496(3) . ? C2 C3 1.498(3) 3_566 ? C3 C2 1.498(3) 3_566 ? C4 C5 1.370(2) . ? C4 C8 1.414(2) 3_676 ? C5 C6 1.428(2) . ? C6 C7 1.363(3) . ? C7 C8 1.427(2) . ? C8 C4 1.414(2) 3_676 ? C8 C8 1.443(3) 3_676 ? 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 Cu N1 180.0 . 3_566 ? N1 Cu N2 96.05(9) . . ? N1 Cu N2 83.95(9) 3_566 . ? N1 Cu N2 83.95(9) . 3_566 ? N1 Cu N2 96.05(9) 3_566 3_566 ? N2 Cu N2 180.0 . 3_566 ? N1 Cu O1 87.46(9) . . ? N1 Cu O1 92.54(9) 3_566 . ? N2 Cu O1 82.22(7) . . ? N2 Cu O1 97.78(7) 3_566 . ? O1 S1 O3 111.58(11) . . ? O1 S1 O2 113.11(11) . . ? O3 S1 O2 113.66(9) . . ? O1 S1 C6 106.40(10) . . ? O3 S1 C6 104.38(9) . . ? O2 S1 C6 106.91(10) . . ? S1 O1 Cu 156.92(9) . . ? C3 N1 Cu 108.70(14) . . ? C1 N2 C2 111.29(16) . . ? C1 N2 Cu 121.18(14) . . ? C2 N2 Cu 107.14(13) . . ? N2 C2 C3 108.12(16) . 3_566 ? N1 C3 C2 107.88(17) . 3_566 ? C5 C4 C8 121.16(15) . 3_676 ? C4 C5 C6 119.47(16) . . ? C7 C6 C5 121.48(14) . . ? C7 C6 S1 120.74(13) . . ? C5 C6 S1 117.78(13) . . ? C6 C7 C8 120.16(15) . . ? C4 C8 C7 122.28(15) 3_676 . ? C4 C8 C8 119.09(17) 3_676 3_676 ? C7 C8 C8 118.63(17) . 3_676 ? 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 O3 S1 O1 Cu 176.38(19) . . . . ? O2 S1 O1 Cu 46.7(2) . . . . ? C6 S1 O1 Cu -70.4(2) . . . . ? N1 Cu O1 S1 139.9(2) . . . . ? N1 Cu O1 S1 -40.1(2) 3_566 . . . ? N2 Cu O1 S1 -123.6(2) . . . . ? N2 Cu O1 S1 56.4(2) 3_566 . . . ? N1 Cu N1 C3 -113(21) 3_566 . . . ? N2 Cu N1 C3 163.87(12) . . . . ? N2 Cu N1 C3 -16.13(12) 3_566 . . . ? O1 Cu N1 C3 -114.23(13) . . . . ? N1 Cu N2 C1 -37.94(16) . . . . ? N1 Cu N2 C1 142.06(16) 3_566 . . . ? N2 Cu N2 C1 -101(100) 3_566 . . . ? O1 Cu N2 C1 -124.53(16) . . . . ? N1 Cu N2 C2 -167.04(11) . . . . ? N1 Cu N2 C2 12.96(11) 3_566 . . . ? N2 Cu N2 C2 130(100) 3_566 . . . ? O1 Cu N2 C2 106.37(13) . . . . ? C1 N2 C2 C3 -173.92(16) . . . 3_566 ? Cu N2 C2 C3 -39.37(17) . . . 3_566 ? Cu N1 C3 C2 42.33(18) . . . 3_566 ? C8 C4 C5 C6 -0.4(3) 3_676 . . . ? C4 C5 C6 C7 1.2(2) . . . . ? C4 C5 C6 S1 -178.47(13) . . . . ? O1 S1 C6 C7 118.61(15) . . . . ? O3 S1 C6 C7 -123.27(14) . . . . ? O2 S1 C6 C7 -2.54(15) . . . . ? O1 S1 C6 C5 -61.74(15) . . . . ? O3 S1 C6 C5 56.38(14) . . . . ? O2 S1 C6 C5 177.12(12) . . . . ? C5 C6 C7 C8 -1.3(2) . . . . ? S1 C6 C7 C8 178.31(12) . . . . ? C6 C7 C8 C4 -179.24(16) . . . 3_676 ? C6 C7 C8 C8 0.7(3) . . . 3_676 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O3 0.90 2.44 3.142(4) 134.6 3_666 N1 H1B OW 0.90 2.10 2.942(3) 156.4 4_565 N2 H2C O1 0.91 2.54 3.018(3) 113.4 . OW HW1 O3 0.87 1.96 2.831(3) 176.2 . OW HW2 O2 0.90 1.98 2.880(3) 177.5 2_546 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 30.31 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.332 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.054 #=============================================END data_compound3 _database_code_ 157237 _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(1,2-diaminopropane)-copper(II) 4,4'-biphenyldisulfonate ; _chemical_name_common Cu(dpn)2(bpds) _chemical_melting_point ? _chemical_formula_moiety Cu1 C6 H20 N4 2+, C12 H8 S2 O6 2- _chemical_formula_sum 'C18 H28 Cu N4 O6 S2' _chemical_formula_weight 524.10 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' 'S' 'S' 0.1246 0.1234 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.486(2) _cell_length_b 7.9921(7) _cell_length_c 12.3656(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.839(2) _cell_angle_gamma 90.00 _cell_volume 2221.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.17 _cell_measurement_theta_max 30.03 _exptl_crystal_description plate _exptl_crystal_colour deep blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 1.214 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.7122 _exptl_absorpt_correction_T_max 0.9091 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7499 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3168 _reflns_number_gt 2715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0536P)^2^+1.9511P] 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 3168 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.2500 0.2500 0.0000 0.02753(11) Uani 1 2 d S . . N1 N 0.17285(8) 0.2326(2) -0.12209(15) 0.0345(4) Uani 1 1 d . . . H1C H 0.1560 0.3343 -0.1371 0.041 Uiso 1 1 calc R A 1 H1D H 0.1792 0.1927 -0.1857 0.041 Uiso 1 1 calc R A 1 N2 N 0.20437(8) 0.1590(2) 0.10221(14) 0.0323(4) Uani 1 1 d . . . H2B H 0.2179 0.0566 0.1270 0.039 Uiso 1 1 calc R C . H2C H 0.2091 0.2265 0.1625 0.039 Uiso 1 1 calc R . . C1 C 0.14148(11) 0.1500(4) 0.0381(2) 0.0514(6) Uani 1 1 d . C . H1A H 0.1222 0.2543 0.0467 0.062 Uiso 1 1 calc R B 1 H1B H 0.1226 0.0609 0.0685 0.062 Uiso 1 1 calc R B 1 C2A C 0.13315(12) 0.1186(4) -0.0837(3) 0.0318(6) Uani 0.70 1 d P C 1 H2AA H 0.1450 0.0031 -0.0928 0.038 Uiso 0.70 1 calc PR C 1 C2B C 0.1238(4) 0.2158(13) -0.0668(8) 0.0477(19) Uiso 0.30 1 d P C 2 H2BA H 0.1126 0.3313 -0.0556 0.057 Uiso 0.30 1 calc PR C 2 C3 C 0.06794(12) 0.1414(5) -0.1538(3) 0.0707(9) Uani 1 1 d . . . H3A H 0.0643 0.1227 -0.2322 0.106 Uiso 1 1 calc R C 1 H3B H 0.0553 0.2531 -0.1439 0.106 Uiso 1 1 calc R C 1 H3C H 0.0435 0.0627 -0.1291 0.106 Uiso 1 1 calc R C 1 S1 S 0.30755(2) -0.12808(6) -0.10854(4) 0.02680(12) Uani 1 1 d . C . O3 O 0.29147(8) -0.2938(2) -0.15697(13) 0.0399(4) Uani 1 1 d . . . O2 O 0.32729(7) -0.0185(2) -0.18483(12) 0.0393(3) Uani 1 1 d . . . O1 O 0.26224(7) -0.0530(2) -0.06514(13) 0.0398(3) Uani 1 1 d . . . C4 C 0.37124(8) -0.1542(2) 0.01074(15) 0.0284(4) Uani 1 1 d . . . C5 C 0.42717(10) -0.1626(4) -0.00375(18) 0.0502(6) Uani 1 1 d . C . H5AA H 0.4315 -0.1609 -0.0762 0.060 Uiso 1 1 calc R . . C6 C 0.47725(10) -0.1737(5) 0.08950(19) 0.0547(7) Uani 1 1 d . . . H6AA H 0.5146 -0.1810 0.0781 0.066 Uiso 1 1 calc R C . C7 C 0.47291(8) -0.1741(3) 0.19971(16) 0.0320(4) Uani 1 1 d . . . C8 C 0.41590(9) -0.1698(3) 0.21155(16) 0.0341(4) Uani 1 1 d . . . H8AA H 0.4113 -0.1733 0.2837 0.041 Uiso 1 1 calc R C . C9 C 0.36539(9) -0.1605(3) 0.11884(16) 0.0320(4) Uani 1 1 d . C . H9AA H 0.3278 -0.1585 0.1296 0.038 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 Cu 0.02499(17) 0.03401(19) 0.02193(17) 0.00449(12) 0.00417(12) -0.00206(12) N1 0.0333(9) 0.0400(10) 0.0267(8) 0.0022(7) 0.0033(7) 0.0000(7) N2 0.0371(9) 0.0323(8) 0.0273(8) 0.0017(6) 0.0091(7) -0.0026(7) C1 0.0348(11) 0.0733(18) 0.0474(13) 0.0064(12) 0.0140(10) -0.0091(11) C2A 0.0268(12) 0.0242(13) 0.0403(15) -0.0033(11) 0.0032(11) -0.0021(10) C3 0.0390(14) 0.090(2) 0.0683(19) 0.0111(17) -0.0084(13) -0.0163(14) S1 0.0299(2) 0.0273(2) 0.0211(2) 0.00065(15) 0.00396(16) -0.00101(16) O3 0.0507(9) 0.0321(8) 0.0304(7) -0.0052(6) 0.0012(7) -0.0073(7) O2 0.0468(8) 0.0396(8) 0.0309(7) 0.0082(6) 0.0102(6) -0.0056(7) O1 0.0348(7) 0.0477(9) 0.0357(8) 0.0017(7) 0.0085(6) 0.0085(6) C4 0.0299(9) 0.0297(9) 0.0235(8) -0.0022(7) 0.0045(7) -0.0004(7) C5 0.0353(11) 0.093(2) 0.0219(9) -0.0001(11) 0.0081(8) 0.0027(12) C6 0.0284(11) 0.109(2) 0.0274(10) -0.0009(12) 0.0095(8) 0.0041(12) C7 0.0294(9) 0.0410(11) 0.0237(8) -0.0005(8) 0.0047(7) -0.0002(8) C8 0.0312(9) 0.0484(12) 0.0222(8) 0.0020(8) 0.0070(7) 0.0014(8) C9 0.0285(9) 0.0410(11) 0.0264(9) 0.0004(8) 0.0080(7) 0.0019(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 1.9992(18) . ? Cu N1 1.9992(18) 7 ? Cu N2 2.0147(17) . ? Cu N2 2.0147(17) 7 ? Cu O1 2.5946(16) . ? N1 C2A 1.477(3) . ? N1 C2B 1.507(10) . ? N2 C1 1.462(3) . ? C1 C2B 1.349(10) . ? C1 C2A 1.483(4) . ? C2A C3 1.537(4) . ? C2B C3 1.553(10) . ? S1 O1 1.4528(15) . ? S1 O2 1.4577(15) . ? S1 O3 1.4579(16) . ? S1 C4 1.7829(19) . ? C4 C5 1.378(3) . ? C4 C9 1.384(3) . ? C5 C6 1.391(3) . ? C6 C7 1.396(3) . ? C7 C8 1.389(3) . ? C7 C7 1.500(4) 2_655 ? C8 C9 1.393(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N1 180.00(17) . 7 ? N1 Cu N2 85.30(7) . . ? N1 Cu N2 94.70(7) 7 . ? N1 Cu N2 94.70(7) . 7 ? N1 Cu N2 85.30(7) 7 7 ? N2 Cu N2 180.00(12) . 7 ? N1 Cu O1 81.85(6) . . ? N1 Cu O1 98.15(6) 7 . ? N2 Cu O1 89.13(6) . . ? N2 Cu O1 90.87(6) 7 . ? C2A N1 C2B 33.1(4) . . ? C2A N1 Cu 108.59(15) . . ? C2B N1 Cu 108.0(4) . . ? C1 N2 Cu 108.37(14) . . ? C2B C1 N2 118.9(4) . . ? C2B C1 C2A 34.5(4) . . ? N2 C1 C2A 112.0(2) . . ? N1 C2A C1 108.2(2) . . ? N1 C2A C3 111.4(2) . . ? C1 C2A C3 111.7(3) . . ? C1 C2B N1 114.0(7) . . ? C1 C2B C3 118.7(7) . . ? N1 C2B C3 108.9(6) . . ? C2A C3 C2B 31.9(4) . . ? O1 S1 O2 113.30(10) . . ? O1 S1 O3 113.37(10) . . ? O2 S1 O3 111.90(10) . . ? O1 S1 C4 105.75(9) . . ? O2 S1 C4 104.93(9) . . ? O3 S1 C4 106.79(9) . . ? S1 O1 Cu 131.22(10) . . ? C5 C4 C9 119.28(18) . . ? C5 C4 S1 120.07(15) . . ? C9 C4 S1 120.61(15) . . ? C4 C5 C6 120.3(2) . . ? C5 C6 C7 121.7(2) . . ? C8 C7 C6 116.63(18) . . ? C8 C7 C7 121.7(2) . 2_655 ? C6 C7 C7 121.7(2) . 2_655 ? C7 C8 C9 122.13(18) . . ? C4 C9 C8 119.86(18) . . ? 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 Cu N1 C2A -60(100) 7 . . . ? N2 Cu N1 C2A -18.05(16) . . . . ? N2 Cu N1 C2A 161.95(16) 7 . . . ? O1 Cu N1 C2A 71.74(16) . . . . ? N1 Cu N1 C2B -25(100) 7 . . . ? N2 Cu N1 C2B 16.9(4) . . . . ? N2 Cu N1 C2B -163.1(4) 7 . . . ? O1 Cu N1 C2B 106.6(4) . . . . ? N1 Cu N2 C1 -6.64(17) . . . . ? N1 Cu N2 C1 173.36(17) 7 . . . ? N2 Cu N2 C1 -35(100) 7 . . . ? O1 Cu N2 C1 -88.53(17) . . . . ? Cu N2 C1 C2B -6.9(6) . . . . ? Cu N2 C1 C2A 30.7(3) . . . . ? C2B N1 C2A C1 -55.9(7) . . . . ? Cu N1 C2A C1 38.8(3) . . . . ? C2B N1 C2A C3 67.2(7) . . . . ? Cu N1 C2A C3 161.8(2) . . . . ? C2B C1 C2A N1 63.0(7) . . . . ? N2 C1 C2A N1 -46.5(3) . . . . ? C2B C1 C2A C3 -60.0(7) . . . . ? N2 C1 C2A C3 -169.5(2) . . . . ? N2 C1 C2B N1 22.0(9) . . . . ? C2A C1 C2B N1 -65.2(7) . . . . ? N2 C1 C2B C3 152.3(5) . . . . ? C2A C1 C2B C3 65.1(8) . . . . ? C2A N1 C2B C1 71.2(8) . . . . ? Cu N1 C2B C1 -25.4(8) . . . . ? C2A N1 C2B C3 -63.8(7) . . . . ? Cu N1 C2B C3 -160.5(4) . . . . ? N1 C2A C3 C2B -67.4(7) . . . . ? C1 C2A C3 C2B 53.7(7) . . . . ? C1 C2B C3 C2A -69.7(8) . . . . ? N1 C2B C3 C2A 62.9(7) . . . . ? O2 S1 O1 Cu -39.17(14) . . . . ? O3 S1 O1 Cu -168.10(10) . . . . ? C4 S1 O1 Cu 75.23(12) . . . . ? N1 Cu O1 S1 121.25(12) . . . . ? N1 Cu O1 S1 -58.75(12) 7 . . . ? N2 Cu O1 S1 -153.37(12) . . . . ? N2 Cu O1 S1 26.63(12) 7 . . . ? O1 S1 C4 C5 -155.9(2) . . . . ? O2 S1 C4 C5 -35.8(2) . . . . ? O3 S1 C4 C5 83.1(2) . . . . ? O1 S1 C4 C9 21.9(2) . . . . ? O2 S1 C4 C9 141.96(18) . . . . ? O3 S1 C4 C9 -99.11(19) . . . . ? C9 C4 C5 C6 -1.4(4) . . . . ? S1 C4 C5 C6 176.4(3) . . . . ? C4 C5 C6 C7 -1.0(5) . . . . ? C5 C6 C7 C8 2.6(5) . . . . ? C5 C6 C7 C7 -175.7(2) . . . 2_655 ? C6 C7 C8 C9 -1.9(4) . . . . ? C7 C7 C8 C9 176.38(16) 2_655 . . . ? C5 C4 C9 C8 2.0(3) . . . . ? S1 C4 C9 C8 -175.77(17) . . . . ? C7 C8 C9 C4 -0.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1C O2 0.90 2.63 3.107(2) 114.4 4_554 N1 H1D O3 0.90 2.25 3.088(3) 155.4 4_554 N2 H2B O3 0.90 2.15 2.991(2) 154.4 7_545 N2 H2C O3 0.90 2.55 3.269(2) 137.0 6_556 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.551 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.073 #=============================================END data_compound4 _database_code_ 157238 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1,4,8,11-tetraazacyclotetradecane)-copper(II) naphthalene-1,5-disulfonate ; _chemical_name_common Cu(cyclam)(1,5nds) _chemical_melting_point ? _chemical_formula_moiety Cu1 C10 H24 N4 2+, C10 H6 S2 O6 2- _chemical_formula_sum 'C20 H30 Cu N4 O6 S2' _chemical_formula_weight 550.14 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.568(6) _cell_length_b 10.521(8) _cell_length_c 12.839(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.869(15) _cell_angle_gamma 90.00 _cell_volume 1156.8(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 26.37 _exptl_crystal_description block _exptl_crystal_colour deep purple _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 574 _exptl_absorpt_coefficient_mu 1.170 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.8441 _exptl_absorpt_correction_T_max 0.9547 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6658 _diffrn_reflns_av_R_equivalents 0.0924 _diffrn_reflns_av_sigmaI/netI 0.0784 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2332 _reflns_number_gt 1704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2332 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1372 _refine_ls_R_factor_gt 0.1181 _refine_ls_wR_factor_ref 0.3670 _refine_ls_wR_factor_gt 0.3564 _refine_ls_goodness_of_fit_ref 1.426 _refine_ls_restrained_S_all 1.426 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.5000 0.0000 1.0000 0.0313(6) Uani 1 2 d S . . S1 S 0.2510(2) 0.2496(2) 0.97364(18) 0.0350(7) Uani 1 1 d . . . N1 N 0.6217(10) 0.1216(8) 0.9147(7) 0.045(2) Uani 1 1 d . . . H1D H 0.5640 0.1941 0.9094 0.054 Uiso 1 1 calc R . . N2 N 0.6457(9) 0.0498(9) 1.1194(7) 0.045(2) Uani 1 1 d . . . H2D H 0.7197 -0.0121 1.1252 0.054 Uiso 1 1 calc R . . O1 O 0.3206(8) 0.1736(7) 1.0563(6) 0.0464(18) Uani 1 1 d . . . O2 O 0.1477(10) 0.1770(8) 0.9044(7) 0.062(2) Uani 1 1 d . . . O3 O 0.3648(9) 0.3216(7) 0.9172(7) 0.062(2) Uani 1 1 d . . . C1 C 0.6522(13) 0.0811(11) 0.8073(9) 0.053(3) Uani 1 1 d . . . H1B H 0.7162 0.0051 0.8098 0.064 Uiso 1 1 calc R . . H1C H 0.7108 0.1472 0.7732 0.064 Uiso 1 1 calc R . . C2 C 0.5066(15) 0.0545(11) 0.7441(9) 0.054(3) Uani 1 1 d . . . H2B H 0.5330 0.0456 0.6716 0.065 Uiso 1 1 calc R . . H2C H 0.4368 0.1267 0.7492 0.065 Uiso 1 1 calc R . . C3 C 0.7637(12) 0.1537(11) 0.9769(10) 0.057(3) Uani 1 1 d . . . H3B H 0.8412 0.0874 0.9694 0.068 Uiso 1 1 calc R . . H3C H 0.8072 0.2327 0.9519 0.068 Uiso 1 1 calc R . . C4 C 0.7261(14) 0.1667(11) 1.0855(10) 0.056(3) Uani 1 1 d . . . H4A H 0.6589 0.2398 1.0944 0.067 Uiso 1 1 calc R . . H4B H 0.8210 0.1795 1.1275 0.067 Uiso 1 1 calc R . . C5 C 0.5780(15) 0.0634(12) 1.2225(9) 0.056(3) Uani 1 1 d . . . H5A H 0.5057 0.1344 1.2210 0.067 Uiso 1 1 calc R . . H5B H 0.6607 0.0826 1.2735 0.067 Uiso 1 1 calc R . . C6 C 0.0542(11) 0.4650(9) 0.8649(8) 0.039(2) Uani 1 1 d . . . H6A H 0.1127 0.4059 0.8291 0.047 Uiso 1 1 calc R . . C7 C 0.0485(10) 0.4561(8) 0.9732(7) 0.0303(18) Uani 1 1 d . . . C8 C 0.1292(10) 0.3619(8) 1.0331(7) 0.0311(18) Uani 1 1 d . . . C9 C 0.1159(10) 0.3569(9) 1.1391(8) 0.039(2) Uani 1 1 d . . . H9A H 0.1701 0.2950 1.1773 0.046 Uiso 1 1 calc R . . C10 C 0.0229(12) 0.4429(12) 1.1899(7) 0.045(2) Uani 1 1 d . . . H10A H 0.0133 0.4375 1.2617 0.054 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 Cu 0.0304(9) 0.0202(9) 0.0435(10) -0.0026(5) 0.0039(6) -0.0007(5) S1 0.0361(12) 0.0237(11) 0.0450(14) -0.0036(8) 0.0007(9) 0.0113(8) N1 0.040(4) 0.035(4) 0.061(5) 0.002(4) 0.015(4) 0.008(3) N2 0.033(4) 0.046(5) 0.055(5) -0.006(4) -0.001(3) 0.005(4) O1 0.052(4) 0.034(4) 0.052(4) 0.000(3) -0.004(3) 0.020(3) O2 0.065(5) 0.050(5) 0.070(5) -0.031(4) -0.021(4) 0.024(4) O3 0.061(5) 0.041(4) 0.087(6) 0.017(4) 0.032(4) 0.019(4) C1 0.061(7) 0.042(6) 0.058(6) 0.010(5) 0.024(5) 0.015(5) C2 0.080(8) 0.034(6) 0.049(6) 0.008(5) 0.009(5) 0.013(5) C3 0.037(5) 0.040(6) 0.094(9) 0.003(6) 0.011(5) -0.014(4) C4 0.056(6) 0.035(5) 0.075(8) -0.017(5) 0.001(6) -0.008(5) C5 0.071(7) 0.051(7) 0.046(6) -0.015(5) -0.005(5) 0.013(6) C6 0.044(5) 0.028(4) 0.045(5) 0.002(4) 0.005(4) 0.013(4) C7 0.032(4) 0.018(4) 0.042(5) -0.004(4) 0.002(3) 0.008(3) C8 0.035(4) 0.020(4) 0.038(5) -0.003(3) 0.000(3) 0.002(3) C9 0.036(5) 0.037(5) 0.042(5) 0.005(4) -0.003(4) 0.007(4) C10 0.048(5) 0.062(7) 0.026(5) -0.003(4) -0.004(4) 0.015(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 2.000(9) 3_657 ? Cu N1 2.000(9) . ? Cu N2 2.014(8) . ? Cu N2 2.014(8) 3_657 ? Cu O1 2.509(7) . ? S1 O1 1.443(7) . ? S1 O3 1.448(8) . ? S1 O2 1.451(8) . ? S1 C8 1.766(8) . ? N1 C3 1.472(14) . ? N1 C1 1.474(14) . ? N2 C5 1.471(14) . ? N2 C4 1.482(15) . ? C1 C2 1.492(17) . ? C2 C5 1.506(19) 3_657 ? C3 C4 1.448(19) . ? C5 C2 1.506(19) 3_657 ? C6 C10 1.356(15) 3_567 ? C6 C7 1.397(13) . ? C7 C8 1.420(12) . ? C7 C7 1.433(16) 3_567 ? C8 C9 1.370(13) . ? C9 C10 1.383(14) . ? C10 C6 1.356(15) 3_567 ? 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 Cu N1 180.000(1) 3_657 . ? N1 Cu N2 94.1(4) 3_657 . ? N1 Cu N2 85.9(4) . . ? N1 Cu N2 85.9(4) 3_657 3_657 ? N1 Cu N2 94.1(4) . 3_657 ? N2 Cu N2 180.000(1) . 3_657 ? N1 Cu O1 88.4(3) 3_657 . ? N1 Cu O1 91.6(3) . . ? N2 Cu O1 87.8(3) . . ? N2 Cu O1 92.2(3) 3_657 . ? O1 S1 O3 112.9(5) . . ? O1 S1 O2 112.9(5) . . ? O3 S1 O2 112.1(6) . . ? O1 S1 C8 106.8(4) . . ? O3 S1 C8 106.5(4) . . ? O2 S1 C8 105.0(4) . . ? C3 N1 C1 113.9(9) . . ? C3 N1 Cu 106.6(7) . . ? C1 N1 Cu 116.0(7) . . ? C5 N2 C4 112.6(9) . . ? C5 N2 Cu 117.2(7) . . ? C4 N2 Cu 106.0(7) . . ? S1 O1 Cu 115.7(4) . . ? N1 C1 C2 113.1(9) . . ? C1 C2 C5 113.7(9) . 3_657 ? C4 C3 N1 109.8(9) . . ? C3 C4 N2 108.9(9) . . ? N2 C5 C2 112.5(9) . 3_657 ? C10 C6 C7 122.1(9) 3_567 . ? C6 C7 C8 123.6(8) . . ? C6 C7 C7 118.3(10) . 3_567 ? C8 C7 C7 118.0(10) . 3_567 ? C9 C8 C7 120.7(8) . . ? C9 C8 S1 118.2(7) . . ? C7 C8 S1 121.1(6) . . ? C8 C9 C10 120.7(9) . . ? C6 C10 C9 120.1(9) 3_567 . ? 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 Cu N1 C3 101(100) 3_657 . . . ? N2 Cu N1 C3 12.6(7) . . . . ? N2 Cu N1 C3 -167.4(7) 3_657 . . . ? O1 Cu N1 C3 100.3(7) . . . . ? N1 Cu N1 C1 -131(100) 3_657 . . . ? N2 Cu N1 C1 140.7(7) . . . . ? N2 Cu N1 C1 -39.3(7) 3_657 . . . ? O1 Cu N1 C1 -131.6(7) . . . . ? N1 Cu N2 C5 -38.7(8) 3_657 . . . ? N1 Cu N2 C5 141.3(8) . . . . ? N2 Cu N2 C5 -77(100) 3_657 . . . ? O1 Cu N2 C5 49.5(8) . . . . ? N1 Cu N2 C4 -165.4(7) 3_657 . . . ? N1 Cu N2 C4 14.6(7) . . . . ? N2 Cu N2 C4 157(100) 3_657 . . . ? O1 Cu N2 C4 -77.1(7) . . . . ? O3 S1 O1 Cu -64.2(6) . . . . ? O2 S1 O1 Cu 64.2(6) . . . . ? C8 S1 O1 Cu 179.1(4) . . . . ? N1 Cu O1 S1 -128.4(5) 3_657 . . . ? N1 Cu O1 S1 51.6(5) . . . . ? N2 Cu O1 S1 137.5(5) . . . . ? N2 Cu O1 S1 -42.5(5) 3_657 . . . ? C3 N1 C1 C2 -177.5(9) . . . . ? Cu N1 C1 C2 58.2(10) . . . . ? N1 C1 C2 C5 -70.1(13) . . . 3_657 ? C1 N1 C3 C4 -168.3(9) . . . . ? Cu N1 C3 C4 -39.0(10) . . . . ? N1 C3 C4 N2 53.9(12) . . . . ? C5 N2 C4 C3 -169.6(10) . . . . ? Cu N2 C4 C3 -40.2(11) . . . . ? C4 N2 C5 C2 178.8(9) . . . 3_657 ? Cu N2 C5 C2 55.5(12) . . . 3_657 ? C10 C6 C7 C8 -179.2(10) 3_567 . . . ? C10 C6 C7 C7 3.1(17) 3_567 . . 3_567 ? C6 C7 C8 C9 -178.6(10) . . . . ? C7 C7 C8 C9 -0.9(15) 3_567 . . . ? C6 C7 C8 S1 2.2(13) . . . . ? C7 C7 C8 S1 179.9(8) 3_567 . . . ? O1 S1 C8 C9 -2.3(9) . . . . ? O3 S1 C8 C9 -123.2(8) . . . . ? O2 S1 C8 C9 117.8(8) . . . . ? O1 S1 C8 C7 176.9(7) . . . . ? O3 S1 C8 C7 56.0(8) . . . . ? O2 S1 C8 C7 -63.0(8) . . . . ? C7 C8 C9 C10 0.4(14) . . . . ? S1 C8 C9 C10 179.6(8) . . . . ? C8 C9 C10 C6 -1.2(16) . . . 3_567 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1D O3 0.91 2.18 3.046(10) 159.7 . N2 H2D O2 0.91 2.12 2.992(11) 161.6 3_657 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.707 _refine_diff_density_min -1.371 _refine_diff_density_rms 0.211 #================================================END data_compound5 _database_code_ 157239 _audit_creation_method SHELXL-97 _chemical_name_systematic ; diaquo-bis(1,2-diaminopropane)-copper(II) naphthalene-1,5-disulfonate ; _chemical_name_common [Cu(dpn)2(H2O)2](1,5nds) _chemical_melting_point ? _chemical_formula_moiety Cu1 C6 H24 N4 O2 2+, C10 H6 S2 O6 2- _chemical_formula_sum 'C16 H30 Cu N4 O8 S2' _chemical_formula_weight 534.10 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.3699(8) _cell_length_b 9.1849(7) _cell_length_c 23.8804(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.6430(10) _cell_angle_gamma 90.00 _cell_volume 2259.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 30.03 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1108 _exptl_absorpt_coefficient_mu 1.201 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.7952 _exptl_absorpt_correction_T_max 0.8404 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15624 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 30.03 _reflns_number_total 6453 _reflns_number_gt 3817 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0801P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6453 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1634 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.083 _refine_ls_shift/su_mean 0.004 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 0.5000 0.5000 0.0000 0.03454(15) Uani 1 2 d S . . Cu2 Cu 1.0000 0.0000 0.0000 0.03881(16) Uani 1 2 d S . . S1 S 0.46247(10) 0.00398(9) 0.11719(4) 0.0516(2) Uani 1 1 d . . . S2 S 0.41644(9) 0.03044(10) 0.40359(4) 0.0447(2) Uani 1 1 d . . . O1 O 0.3288(3) -0.0342(4) 0.10286(12) 0.0783(9) Uani 1 1 d . . . O2 O 0.4921(3) 0.1539(3) 0.10797(11) 0.0767(9) Uani 1 1 d . . . O3 O 0.5480(3) -0.0919(3) 0.08992(11) 0.0701(8) Uani 1 1 d . . . O4 O 0.3203(2) 0.1100(3) 0.43090(10) 0.0564(6) Uani 1 1 d . . . O5 O 0.4010(3) -0.1254(3) 0.40743(11) 0.0666(8) Uani 1 1 d . . . O6 O 0.5460(2) 0.0822(3) 0.41993(11) 0.0637(7) Uani 1 1 d . . . N1 N 0.4406(3) 0.4686(3) 0.07613(11) 0.0385(6) Uani 1 1 d . . . H1A H 0.3620 0.5095 0.0770 0.046 Uiso 1 1 calc R . . H1B H 0.4332 0.3725 0.0825 0.046 Uiso 1 1 calc R . . N2 N 0.6652(3) 0.5743(3) 0.04303(11) 0.0494(7) Uani 1 1 d . . . H2B H 0.7345 0.5328 0.0300 0.059 Uiso 1 1 calc R . . H2C H 0.6710 0.6715 0.0391 0.059 Uiso 1 1 calc R . . N3 N 1.0256(3) -0.0821(3) 0.07772(10) 0.0421(6) Uani 1 1 d . . . H3B H 0.9886 -0.1708 0.0778 0.051 Uiso 1 1 calc R . . H3C H 1.1111 -0.0924 0.0888 0.051 Uiso 1 1 calc R . . N4 N 0.8877(3) 0.1485(3) 0.03336(12) 0.0481(7) Uani 1 1 d . . . H4B H 0.9302 0.2337 0.0385 0.058 Uiso 1 1 calc R . . H4C H 0.8142 0.1635 0.0101 0.058 Uiso 1 1 calc R . . C1 C 0.4995(3) -0.0280(3) 0.19119(14) 0.0416(7) Uani 1 1 d . . . C2 C 0.5971(3) -0.1187(4) 0.20860(14) 0.0469(8) Uani 1 1 d . . . H2A H 0.6440 -0.1616 0.1820 0.056 Uiso 1 1 calc R . . C3 C 0.6305(3) -0.1507(4) 0.26578(14) 0.0481(8) Uani 1 1 d . . . H3A H 0.6994 -0.2130 0.2768 0.058 Uiso 1 1 calc R . . C4 C 0.5614(3) -0.0897(3) 0.30548(14) 0.0434(8) Uani 1 1 d . . . H4A H 0.5824 -0.1132 0.3433 0.052 Uiso 1 1 calc R . . C5 C 0.3841(3) 0.0728(3) 0.32979(13) 0.0393(7) Uani 1 1 d . . . C6 C 0.2861(3) 0.1672(4) 0.31296(16) 0.0510(8) Uani 1 1 d . . . H6A H 0.2387 0.2089 0.3396 0.061 Uiso 1 1 calc R . . C7 C 0.2559(3) 0.2021(4) 0.25551(16) 0.0567(9) Uani 1 1 d . . . H7A H 0.1892 0.2676 0.2448 0.068 Uiso 1 1 calc R . . C8 C 0.3224(3) 0.1419(4) 0.21536(16) 0.0531(9) Uani 1 1 d . . . H8A H 0.3005 0.1657 0.1776 0.064 Uiso 1 1 calc R . . C9 C 0.4267(3) 0.0413(3) 0.23143(14) 0.0389(7) Uani 1 1 d . . . C10 C 0.4583(3) 0.0087(3) 0.28949(14) 0.0375(7) Uani 1 1 d . . . C11 C 0.6613(4) 0.5365(6) 0.10253(16) 0.0782(14) Uani 1 1 d . . . H11A H 0.7016 0.4420 0.1096 0.094 Uiso 1 1 calc R . . H11B H 0.7124 0.6071 0.1257 0.094 Uiso 1 1 calc R . . C12 C 0.5321(5) 0.5319(5) 0.11969(17) 0.0726(13) Uani 1 1 d . . . H12A H 0.5063 0.6346 0.1201 0.087 Uiso 1 1 calc R . . C13 C 0.5231(5) 0.4827(4) 0.17850(16) 0.0647(11) Uani 1 1 d . . . H13A H 0.4342 0.4863 0.1861 0.097 Uiso 1 1 calc R . . H13B H 0.5746 0.5453 0.2043 0.097 Uiso 1 1 calc R . . H13C H 0.5546 0.3846 0.1830 0.097 Uiso 1 1 calc R . . C14 C 0.8575(4) 0.0914(5) 0.08692(16) 0.0642(11) Uani 1 1 d . . . H14A H 0.7839 0.0259 0.0804 0.077 Uiso 1 1 calc R . . H14B H 0.8331 0.1711 0.1102 0.077 Uiso 1 1 calc R . . C15 C 0.9683(5) 0.0127(5) 0.11727(18) 0.0734(14) Uani 1 1 d . . . H15A H 1.0340 0.0868 0.1288 0.088 Uiso 1 1 calc R . . C16 C 0.9403(5) -0.0620(5) 0.17065(17) 0.0743(12) Uani 1 1 d . . . H16A H 1.0179 -0.1080 0.1881 0.111 Uiso 1 1 calc R . . H16B H 0.8741 -0.1342 0.1619 0.111 Uiso 1 1 calc R . . H16C H 0.9111 0.0085 0.1960 0.111 Uiso 1 1 calc R . . OW1 O 0.5970(2) 0.2381(3) 0.00617(10) 0.0546(6) Uani 1 1 d . . . HW1 H 0.5737 0.1925 0.0350 0.081(14) Uiso 1 1 d R . . HW2 H 0.5579 0.1770 -0.0267 0.113(17) Uiso 1 1 d R . . HW3 H 0.1823 0.2580 0.0371 0.097(16) Uiso 1 1 d R . . HW4 H 0.2259 0.1094 0.0426 0.14(2) Uiso 1 1 d R . . OW2 O 1.2007(2) 0.1750(3) 0.02050(11) 0.0602(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0288(3) 0.0408(3) 0.0339(3) 0.0052(2) 0.0034(2) -0.0033(2) Cu2 0.0381(3) 0.0387(3) 0.0401(3) 0.0057(2) 0.0068(2) 0.0110(2) S1 0.0665(6) 0.0451(5) 0.0421(5) 0.0071(4) 0.0018(4) -0.0104(4) S2 0.0427(5) 0.0457(5) 0.0461(5) -0.0024(4) 0.0068(4) -0.0020(4) O1 0.071(2) 0.103(2) 0.0570(18) 0.0133(15) -0.0121(15) -0.0199(17) O2 0.125(3) 0.0465(15) 0.0609(17) 0.0136(13) 0.0187(16) -0.0116(16) O3 0.096(2) 0.0689(19) 0.0467(15) -0.0062(13) 0.0115(14) 0.0029(16) O4 0.0505(15) 0.0603(15) 0.0603(15) -0.0119(12) 0.0156(12) -0.0002(12) O5 0.104(2) 0.0410(14) 0.0582(15) 0.0056(12) 0.0243(15) 0.0018(14) O6 0.0425(15) 0.088(2) 0.0595(16) -0.0076(14) -0.0009(12) -0.0073(14) N1 0.0376(14) 0.0380(14) 0.0407(15) 0.0035(11) 0.0075(11) -0.0010(11) N2 0.0368(15) 0.0608(19) 0.0490(17) 0.0161(14) -0.0025(12) -0.0110(13) N3 0.0440(15) 0.0394(15) 0.0430(15) 0.0066(11) 0.0054(12) 0.0115(12) N4 0.0444(16) 0.0432(16) 0.0575(17) 0.0063(13) 0.0095(13) 0.0132(12) C1 0.0432(18) 0.0392(17) 0.0418(18) 0.0011(13) 0.0026(14) -0.0098(13) C2 0.0402(18) 0.050(2) 0.050(2) -0.0038(15) 0.0035(15) -0.0002(15) C3 0.0392(18) 0.052(2) 0.051(2) -0.0048(16) -0.0022(15) 0.0119(15) C4 0.0433(18) 0.0420(18) 0.0424(18) 0.0006(14) -0.0056(14) 0.0007(14) C5 0.0341(16) 0.0338(16) 0.0493(18) -0.0033(13) 0.0024(13) -0.0046(13) C6 0.0421(19) 0.0438(19) 0.067(2) -0.0001(16) 0.0043(16) 0.0033(15) C7 0.048(2) 0.051(2) 0.070(3) 0.0056(17) -0.0021(18) 0.0209(16) C8 0.049(2) 0.045(2) 0.062(2) 0.0105(17) -0.0037(17) 0.0047(16) C9 0.0396(17) 0.0302(15) 0.0460(18) 0.0028(13) 0.0008(14) -0.0056(12) C10 0.0333(16) 0.0316(16) 0.0465(18) -0.0018(12) 0.0003(13) -0.0064(12) C11 0.040(2) 0.153(4) 0.039(2) 0.005(2) -0.0062(17) -0.002(2) C12 0.100(4) 0.078(3) 0.038(2) 0.0032(19) 0.002(2) -0.037(3) C13 0.078(3) 0.077(3) 0.039(2) 0.0083(18) 0.0093(19) 0.010(2) C14 0.064(3) 0.074(3) 0.057(2) 0.007(2) 0.0204(19) 0.026(2) C15 0.083(3) 0.091(3) 0.048(2) 0.008(2) 0.014(2) 0.037(2) C16 0.087(3) 0.090(3) 0.048(2) 0.009(2) 0.014(2) 0.022(3) OW1 0.0651(16) 0.0514(14) 0.0473(14) 0.0035(12) 0.0071(12) 0.0027(12) OW2 0.0650(17) 0.0541(16) 0.0614(16) 0.0003(14) 0.0062(13) 0.0028(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 2.007(3) 3_665 ? Cu1 N1 2.007(3) . ? Cu1 N2 2.012(3) . ? Cu1 N2 2.012(3) 3_665 ? Cu1 OW1 2.605(2) . ? Cu2 N3 1.993(2) 3_755 ? Cu2 N3 1.993(2) . ? Cu2 N4 2.016(3) 3_755 ? Cu2 N4 2.017(3) . ? Cu2 OW2 2.630(3) . ? S1 O1 1.432(3) . ? S1 O2 1.434(3) . ? S1 O3 1.456(3) . ? S1 C1 1.789(3) . ? S2 O6 1.436(3) . ? S2 O5 1.444(3) . ? S2 O4 1.450(2) . ? S2 C5 1.798(3) . ? N1 C12 1.446(5) . ? N2 C11 1.468(5) . ? N3 C15 1.460(5) . ? N4 C14 1.450(4) . ? C1 C2 1.339(5) . ? C1 C9 1.437(5) . ? C2 C3 1.400(5) . ? C3 C4 1.372(4) . ? C4 C10 1.418(4) . ? C5 C6 1.361(4) . ? C5 C10 1.427(4) . ? C6 C7 1.408(5) . ? C7 C8 1.362(5) . ? C8 C9 1.441(4) . ? C9 C10 1.419(5) . ? C11 C12 1.446(7) . ? C12 C13 1.489(5) . ? C14 C15 1.475(6) . ? C15 C16 1.505(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.0(2) 3_665 . ? N1 Cu1 N2 94.68(11) 3_665 . ? N1 Cu1 N2 85.32(11) . . ? N1 Cu1 N2 85.32(11) 3_665 3_665 ? N1 Cu1 N2 94.68(11) . 3_665 ? N2 Cu1 N2 180.00(14) . 3_665 ? N1 Cu1 OW1 91.55(9) 3_665 . ? N1 Cu1 OW1 88.45(9) . . ? N2 Cu1 OW1 89.09(10) . . ? N2 Cu1 OW1 90.91(10) 3_665 . ? N3 Cu2 N3 180.00(14) 3_755 . ? N3 Cu2 N4 84.77(11) 3_755 3_755 ? N3 Cu2 N4 95.23(11) . 3_755 ? N3 Cu2 N4 95.23(11) 3_755 . ? N3 Cu2 N4 84.77(11) . . ? N4 Cu2 N4 180.0(2) 3_755 . ? N3 Cu2 OW2 87.66(10) 3_755 . ? N3 Cu2 OW2 92.34(10) . . ? N4 Cu2 OW2 90.35(10) 3_755 . ? N4 Cu2 OW2 89.65(10) . . ? O1 S1 O2 114.6(2) . . ? O1 S1 O3 111.59(19) . . ? O2 S1 O3 111.09(18) . . ? O1 S1 C1 106.69(17) . . ? O2 S1 C1 106.51(15) . . ? O3 S1 C1 105.67(17) . . ? O6 S2 O5 114.71(17) . . ? O6 S2 O4 112.39(16) . . ? O5 S2 O4 112.57(16) . . ? O6 S2 C5 104.90(15) . . ? O5 S2 C5 105.50(14) . . ? O4 S2 C5 105.77(15) . . ? C12 N1 Cu1 110.4(2) . . ? C11 N2 Cu1 107.3(2) . . ? C15 N3 Cu2 110.9(2) . . ? C14 N4 Cu2 107.3(2) . . ? C2 C1 C9 120.3(3) . . ? C2 C1 S1 118.5(3) . . ? C9 C1 S1 121.2(3) . . ? C1 C2 C3 121.7(3) . . ? C4 C3 C2 119.9(3) . . ? C3 C4 C10 120.8(3) . . ? C6 C5 C10 120.4(3) . . ? C6 C5 S2 118.4(3) . . ? C10 C5 S2 121.2(2) . . ? C5 C6 C7 120.5(3) . . ? C8 C7 C6 121.3(3) . . ? C7 C8 C9 119.9(3) . . ? C10 C9 C1 118.7(3) . . ? C10 C9 C8 118.5(3) . . ? C1 C9 C8 122.8(3) . . ? C4 C10 C9 118.6(3) . . ? C4 C10 C5 122.0(3) . . ? C9 C10 C5 119.4(3) . . ? C12 C11 N2 114.3(3) . . ? C11 C12 N1 111.1(4) . . ? C11 C12 C13 115.9(4) . . ? N1 C12 C13 116.7(3) . . ? N4 C14 C15 112.1(3) . . ? N3 C15 C14 109.0(3) . . ? N3 C15 C16 114.1(3) . . ? C14 C15 C16 115.1(4) . . ? 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 C12 -126(24) 3_665 . . . ? N2 Cu1 N1 C12 8.4(3) . . . . ? N2 Cu1 N1 C12 -171.6(3) 3_665 . . . ? OW1 Cu1 N1 C12 97.6(3) . . . . ? N1 Cu1 N2 C11 -168.5(3) 3_665 . . . ? N1 Cu1 N2 C11 11.5(3) . . . . ? N2 Cu1 N2 C11 -22(100) 3_665 . . . ? OW1 Cu1 N2 C11 -77.0(3) . . . . ? N3 Cu2 N3 C15 18.8(3) 3_755 . . . ? N4 Cu2 N3 C15 172.7(3) 3_755 . . . ? N4 Cu2 N3 C15 -7.3(3) . . . . ? OW2 Cu2 N3 C15 82.2(3) . . . . ? N3 Cu2 N4 C14 163.7(3) 3_755 . . . ? N3 Cu2 N4 C14 -16.3(3) . . . . ? N4 Cu2 N4 C14 -143(100) 3_755 . . . ? OW2 Cu2 N4 C14 -108.7(2) . . . . ? O1 S1 C1 C2 123.2(3) . . . . ? O2 S1 C1 C2 -113.9(3) . . . . ? O3 S1 C1 C2 4.3(3) . . . . ? O1 S1 C1 C9 -56.7(3) . . . . ? O2 S1 C1 C9 66.1(3) . . . . ? O3 S1 C1 C9 -175.6(3) . . . . ? C9 C1 C2 C3 0.8(5) . . . . ? S1 C1 C2 C3 -179.1(3) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? C2 C3 C4 C10 -1.7(5) . . . . ? O6 S2 C5 C6 -117.3(3) . . . . ? O5 S2 C5 C6 121.2(3) . . . . ? O4 S2 C5 C6 1.7(3) . . . . ? O6 S2 C5 C10 63.1(3) . . . . ? O5 S2 C5 C10 -58.4(3) . . . . ? O4 S2 C5 C10 -177.9(2) . . . . ? C10 C5 C6 C7 0.5(5) . . . . ? S2 C5 C6 C7 -179.1(3) . . . . ? C5 C6 C7 C8 0.7(6) . . . . ? C6 C7 C8 C9 -0.5(5) . . . . ? C2 C1 C9 C10 -1.6(4) . . . . ? S1 C1 C9 C10 178.3(2) . . . . ? C2 C1 C9 C8 178.8(3) . . . . ? S1 C1 C9 C8 -1.3(4) . . . . ? C7 C8 C9 C10 -0.7(5) . . . . ? C7 C8 C9 C1 179.0(3) . . . . ? C3 C4 C10 C9 0.9(4) . . . . ? C3 C4 C10 C5 179.5(3) . . . . ? C1 C9 C10 C4 0.7(4) . . . . ? C8 C9 C10 C4 -179.7(3) . . . . ? C1 C9 C10 C5 -177.9(3) . . . . ? C8 C9 C10 C5 1.7(4) . . . . ? C6 C5 C10 C4 179.8(3) . . . . ? S2 C5 C10 C4 -0.7(4) . . . . ? C6 C5 C10 C9 -1.7(4) . . . . ? S2 C5 C10 C9 177.9(2) . . . . ? Cu1 N2 C11 C12 -30.6(5) . . . . ? N2 C11 C12 N1 39.2(6) . . . . ? N2 C11 C12 C13 175.4(4) . . . . ? Cu1 N1 C12 C11 -27.2(4) . . . . ? Cu1 N1 C12 C13 -163.0(3) . . . . ? Cu2 N4 C14 C15 37.5(4) . . . . ? Cu2 N3 C15 C14 29.1(5) . . . . ? Cu2 N3 C15 C16 159.3(3) . . . . ? N4 C14 C15 N3 -44.7(5) . . . . ? N4 C14 C15 C16 -174.4(4) . . . . ? 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 OW1 HW1 O2 0.86 2.05 2.882(4) 160.1 . OW1 HW2 O3 1.01 1.93 2.921(4) 167.1 3_655 N1 H1A O4 0.90 2.09 2.989(4) 173.3 2 N1 H1B O2 0.90 2.17 3.020(4) 158.4 . N2 H2B O6 0.90 2.49 3.024(4) 118.7 2_655 N2 H2C OW2 0.90 2.49 3.166(4) 131.9 3_765 N3 H3B O6 0.90 2.30 3.173(4) 163.9 2_645 N3 H3C O1 0.90 2.31 3.163(4) 158.8 1_655 N4 H4B O5 0.90 2.43 3.225(4) 148.1 2_655 N4 H4C OW1 0.90 2.35 3.119(4) 144.1 . _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.823 _refine_diff_density_min -0.709 _refine_diff_density_rms 0.077 #==============================================end data_compound6 _database_code_ 157240 _audit_creation_method SHELXL-97 _chemical_name_systematic ; diaquo-bis(N,N'-dimethylethylenediamine)-copper(II) naphthalene-1,5-disulfonate monohydrate ; _chemical_name_common [Cu(Mmen)2(H2O)2](1,5nds).H2O _chemical_melting_point ? _chemical_formula_moiety 'Cu1 C8 H28 N4 O2 2+, C10 H6 S2 O6 2-, H2 O1' _chemical_formula_sum 'C18 H36 Cu N4 O9 S2' _chemical_formula_weight 580.17 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' 'S' 'S' 0.1246 0.1234 '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 8.4923(7) _cell_length_b 8.7434(7) _cell_length_c 9.1900(7) _cell_angle_alpha 92.314(2) _cell_angle_beta 94.938(2) _cell_angle_gamma 113.5570(10) _cell_volume 621.09(9) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.47 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 313 _exptl_absorpt_coefficient_mu 1.107 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.6848 _exptl_absorpt_correction_T_max 0.8515 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4404 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.47 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3393 _reflns_number_gt 3113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1130P)^2^+0.2599P] 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 3393 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1469 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.5000 0.0000 0.5000 0.02857(14) Uani 1 2 d S . . S1 S 0.15368(7) 0.31599(6) 0.27018(6) 0.03562(16) Uani 1 1 d . . . O1 O 0.1551(3) 0.4318(3) 0.3885(2) 0.0576(5) Uani 1 1 d . . . O2 O 0.3127(3) 0.2900(3) 0.2729(3) 0.0572(5) Uani 1 1 d . . . O3 O 0.0026(2) 0.1596(2) 0.2603(2) 0.0466(4) Uani 1 1 d . . . N1 N 0.3673(2) 0.0312(2) 0.6667(2) 0.0358(4) Uani 1 1 d . . . H1D H 0.2646 -0.0597 0.6593 0.043 Uiso 1 1 calc R . . N2 N 0.2982(2) -0.0552(2) 0.3394(2) 0.0340(4) Uani 1 1 d . . . H2C H 0.2963 0.0442 0.3161 0.041 Uiso 1 1 calc R . . C1 C 0.3289(4) 0.1812(4) 0.6682(4) 0.0536(6) Uani 1 1 d . . . H1A H 0.2669 0.1837 0.7503 0.080 Uiso 1 1 calc R . . H1B H 0.2597 0.1782 0.5790 0.080 Uiso 1 1 calc R . . H1C H 0.4351 0.2796 0.6765 0.080 Uiso 1 1 calc R . . C2 C 0.4677(4) 0.0269(4) 0.8044(3) 0.0477(5) Uani 1 1 d . . . H2A H 0.4471 -0.0879 0.8219 0.057 Uiso 1 1 calc R . . H2B H 0.4327 0.0751 0.8860 0.057 Uiso 1 1 calc R . . C3 C 0.3427(3) -0.1263(4) 0.2088(3) 0.0484(6) Uani 1 1 d . . . H3A H 0.2731 -0.1198 0.1219 0.058 Uiso 1 1 calc R . . H3B H 0.3204 -0.2430 0.2187 0.058 Uiso 1 1 calc R . . C4 C 0.1210(3) -0.1629(3) 0.3698(3) 0.0491(6) Uani 1 1 d . . . H4A H 0.0413 -0.1772 0.2845 0.074 Uiso 1 1 calc R . . H4B H 0.0902 -0.1113 0.4504 0.074 Uiso 1 1 calc R . . H4C H 0.1166 -0.2702 0.3942 0.074 Uiso 1 1 calc R . . C5 C 0.1397(2) 0.4117(2) 0.1037(2) 0.0309(4) Uani 1 1 d . . . C6 C 0.2672(3) 0.4385(3) 0.0150(3) 0.0400(5) Uani 1 1 d . . . H6A H 0.3558 0.4045 0.0407 0.048 Uiso 1 1 calc R . . C7 C 0.2657(3) 0.5175(3) -0.1152(3) 0.0416(5) Uani 1 1 d . . . H7A H 0.3541 0.5364 -0.1744 0.050 Uiso 1 1 calc R . . C8 C 0.1353(3) 0.5669(3) -0.1556(2) 0.0345(4) Uani 1 1 d . . . H8A H 0.1357 0.6186 -0.2421 0.041 Uiso 1 1 calc R . . C9 C -0.0007(2) 0.5395(2) -0.0664(2) 0.0281(3) Uani 1 1 d . . . OW1 O 0.3908(2) -0.2959(2) 0.5648(2) 0.0454(4) Uani 1 1 d . . . HW1 H 0.3136 -0.3840 0.5123 0.060(10) Uiso 1 1 d R . . HW2 H 0.4625 -0.3292 0.6054 0.056(9) Uiso 1 1 d R . . OW2 O 0.1257(15) 0.0212(13) 0.0067(13) 0.146(4) Uani 0.50 1 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 Cu 0.0303(2) 0.0304(2) 0.0267(2) 0.00249(12) 0.00262(13) 0.01406(14) S1 0.0389(3) 0.0324(3) 0.0368(3) 0.01208(19) 0.0001(2) 0.0158(2) O1 0.0787(14) 0.0517(11) 0.0409(9) -0.0003(8) -0.0094(9) 0.0284(10) O2 0.0469(9) 0.0680(12) 0.0687(13) 0.0327(10) 0.0043(9) 0.0337(9) O3 0.0510(9) 0.0336(8) 0.0518(10) 0.0170(7) 0.0111(8) 0.0112(7) N1 0.0366(8) 0.0359(8) 0.0345(8) 0.0046(6) 0.0084(7) 0.0132(7) N2 0.0348(8) 0.0294(8) 0.0368(8) 0.0048(6) -0.0010(7) 0.0128(6) C1 0.0608(15) 0.0519(14) 0.0602(16) 0.0071(12) 0.0209(13) 0.0324(12) C2 0.0540(13) 0.0568(14) 0.0300(10) 0.0076(9) 0.0088(9) 0.0189(11) C3 0.0505(13) 0.0510(13) 0.0348(11) -0.0057(9) -0.0031(9) 0.0138(10) C4 0.0344(10) 0.0477(13) 0.0612(15) 0.0079(11) 0.0003(10) 0.0130(9) C5 0.0294(8) 0.0264(8) 0.0367(9) 0.0097(7) 0.0005(7) 0.0112(6) C6 0.0342(9) 0.0425(11) 0.0495(12) 0.0180(9) 0.0083(9) 0.0197(8) C7 0.0364(10) 0.0477(12) 0.0474(12) 0.0171(9) 0.0157(9) 0.0205(9) C8 0.0344(9) 0.0350(9) 0.0367(10) 0.0134(7) 0.0092(8) 0.0148(8) C9 0.0269(7) 0.0230(7) 0.0329(9) 0.0074(6) 0.0027(6) 0.0082(6) OW1 0.0454(9) 0.0366(8) 0.0520(10) 0.0079(7) -0.0026(7) 0.0154(7) OW2 0.174(9) 0.124(7) 0.130(8) -0.040(6) -0.018(8) 0.062(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 Cu N2 2.0481(18) 2_656 ? Cu N2 2.0481(18) . ? Cu N1 2.0492(18) 2_656 ? Cu N1 2.0492(18) . ? Cu OW1 2.4921(17) . ? S1 O3 1.4466(18) . ? S1 O1 1.452(2) . ? S1 O2 1.4545(19) . ? S1 C5 1.791(2) . ? N1 C1 1.473(3) . ? N1 C2 1.474(3) . ? N2 C3 1.475(3) . ? N2 C4 1.479(3) . ? C2 C3 1.512(4) 2_656 ? C3 C2 1.512(4) 2_656 ? C5 C6 1.362(3) . ? C5 C9 1.427(3) 2_565 ? C6 C7 1.408(3) . ? C7 C8 1.369(3) . ? C8 C9 1.422(3) . ? C9 C5 1.427(3) 2_565 ? C9 C9 1.427(4) 2_565 ? 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 Cu N2 180.00(8) 2_656 . ? N2 Cu N1 94.96(8) 2_656 2_656 ? N2 Cu N1 85.04(8) . 2_656 ? N2 Cu N1 85.04(8) 2_656 . ? N2 Cu N1 94.96(8) . . ? N1 Cu N1 180.000(1) 2_656 . ? N2 Cu OW1 88.15(6) 2_656 . ? N2 Cu OW1 91.85(6) . . ? N1 Cu OW1 95.87(7) 2_656 . ? N1 Cu OW1 84.13(7) . . ? O3 S1 O1 112.08(13) . . ? O3 S1 O2 112.03(12) . . ? O1 S1 O2 113.74(15) . . ? O3 S1 C5 106.60(10) . . ? O1 S1 C5 106.42(11) . . ? O2 S1 C5 105.31(11) . . ? C1 N1 C2 111.4(2) . . ? C1 N1 Cu 116.28(15) . . ? C2 N1 Cu 106.50(15) . . ? C3 N2 C4 110.2(2) . . ? C3 N2 Cu 106.93(15) . . ? C4 N2 Cu 119.35(16) . . ? N1 C2 C3 108.4(2) . 2_656 ? N2 C3 C2 108.10(19) . 2_656 ? C6 C5 C9 121.16(18) . 2_565 ? C6 C5 S1 117.84(15) . . ? C9 C5 S1 120.99(15) 2_565 . ? C5 C6 C7 120.41(19) . . ? C8 C7 C6 120.6(2) . . ? C7 C8 C9 120.51(18) . . ? C8 C9 C5 122.67(17) . 2_565 ? C8 C9 C9 119.1(2) . 2_565 ? C5 C9 C9 118.2(2) 2_565 2_565 ? 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 N2 Cu N1 C1 109.41(19) 2_656 . . . ? N2 Cu N1 C1 -70.59(19) . . . . ? N1 Cu N1 C1 -102(100) 2_656 . . . ? OW1 Cu N1 C1 -161.94(19) . . . . ? N2 Cu N1 C2 -15.43(15) 2_656 . . . ? N2 Cu N1 C2 164.57(15) . . . . ? N1 Cu N1 C2 133(100) 2_656 . . . ? OW1 Cu N1 C2 73.22(15) . . . . ? N2 Cu N2 C3 -163(39) 2_656 . . . ? N1 Cu N2 C3 14.11(16) 2_656 . . . ? N1 Cu N2 C3 -165.89(16) . . . . ? OW1 Cu N2 C3 -81.62(16) . . . . ? N2 Cu N2 C4 -37(39) 2_656 . . . ? N1 Cu N2 C4 139.93(18) 2_656 . . . ? N1 Cu N2 C4 -40.07(18) . . . . ? OW1 Cu N2 C4 44.20(18) . . . . ? C1 N1 C2 C3 -85.9(3) . . . 2_656 ? Cu N1 C2 C3 41.8(2) . . . 2_656 ? C4 N2 C3 C2 -171.7(2) . . . 2_656 ? Cu N2 C3 C2 -40.6(2) . . . 2_656 ? O3 S1 C5 C6 -118.11(19) . . . . ? O1 S1 C5 C6 122.1(2) . . . . ? O2 S1 C5 C6 1.1(2) . . . . ? O3 S1 C5 C9 62.83(18) . . . 2_565 ? O1 S1 C5 C9 -56.96(19) . . . 2_565 ? O2 S1 C5 C9 -178.01(17) . . . 2_565 ? C9 C5 C6 C7 0.8(4) 2_565 . . . ? S1 C5 C6 C7 -178.22(19) . . . . ? C5 C6 C7 C8 -0.7(4) . . . . ? C6 C7 C8 C9 0.2(4) . . . . ? C7 C8 C9 C5 -179.9(2) . . . 2_565 ? C7 C8 C9 C9 0.3(4) . . . 2_565 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1D O3 0.91 2.28 3.060(3) 143.1 2_556 N2 H2C O2 0.91 2.15 3.060(3) 175.0 . OW1 HW1 O1 0.88 1.89 2.761(3) 176.2 1_545 OW1 HW2 O2 0.84 2.02 2.795(3) 152.5 2_656 _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.923 _refine_diff_density_min -1.333 _refine_diff_density_rms 0.098