data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'Cu (H2 O)2 (C17 H9 N O8 S), (H2 O)' _chemical_formula_sum 'C17 H15 Cu N O11 S' _chemical_formula_weight 504.90 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1430(6) _cell_length_b 9.5075(7) _cell_length_c 13.1111(10) _cell_angle_alpha 79.967(1) _cell_angle_beta 73.074(1) _cell_angle_gamma 78.093(1) _cell_volume 943.10(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3204 _cell_measurement_theta_min 2.5811 _cell_measurement_theta_max 28.3165 _exptl_crystal_description blue _exptl_crystal_colour prism _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 1.335 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5397 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABA _diffrn_ambient_temperature 296(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 SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5718 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4188 _reflns_number_gt 3645 _reflns_threshold_expression I>2\w(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'APEX2 (Bruker, 2009)' _computing_data_reduction 'APEX2 (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'publCIF (westrip, 2010)' _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^)+(0.1335P)^2^] 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 4188 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1712 _refine_ls_wR_factor_gt 0.1644 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _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 Cu1 Cu 0.56104(4) 0.47504(4) 0.76961(3) 0.01869(17) Uani 1 1 d . . . S1 S 1.71034(9) 1.19925(7) 0.09032(6) 0.0190(2) Uani 1 1 d . . . O1 O 0.6796(3) 0.5911(2) 0.64367(18) 0.0237(5) Uani 1 1 d . . . O2 O 0.9277(3) 0.6157(3) 0.6728(2) 0.0350(6) Uani 1 1 d . . . O3 O 0.4766(3) 0.8496(3) 0.5664(2) 0.0322(6) Uani 1 1 d . . . H3 H 0.3700 0.8509 0.5960 0.048 Uiso 1 1 d R . . O4 O 0.4858(3) 0.6852(3) 0.4626(2) 0.0406(7) Uani 1 1 d . . . O5 O 1.2728(3) 0.7483(2) 0.29079(19) 0.0243(5) Uani 1 1 d . . . O6 O 1.6150(3) 1.3318(2) 0.1333(2) 0.0328(6) Uani 1 1 d . . . O7 O 1.7637(3) 1.2148(2) -0.02671(18) 0.0286(5) Uani 1 1 d . . . O8 O 1.8549(3) 1.1341(2) 0.13651(19) 0.0279(5) Uani 1 1 d . . . O1w O 0.3751(3) 0.4885(3) 0.6963(2) 0.0277(5) Uani 1 1 d . . . H11 H 0.4187 0.4565 0.6368 0.042 Uiso 1 1 d R . . H12 H 0.3284 0.5754 0.6866 0.042 Uiso 1 1 d R . . O2w O 0.7362(3) 0.4710(2) 0.84757(19) 0.0253(5) Uani 1 1 d . . . H22 H 0.7673 0.3854 0.8728 0.038 Uiso 1 1 d R . . H21 H 0.8229 0.5036 0.8052 0.038 Uiso 1 1 d R . . O3w O 0.1727(3) 0.7709(3) 0.6735(2) 0.0444(7) Uani 1 1 d . . . H31 H 0.1023 0.7787 0.6363 0.067 Uiso 1 1 d R . . H32 H 0.1254 0.8068 0.7314 0.067 Uiso 1 1 d R . . N1 N 1.5510(3) 0.6834(3) 0.1299(2) 0.0188(5) Uani 1 1 d . . . C1 C 0.8259(4) 0.6328(3) 0.6154(2) 0.0186(6) Uani 1 1 d . . . C2 C 0.8742(4) 0.7087(3) 0.5027(2) 0.0182(6) Uani 1 1 d . . . C3 C 1.0495(4) 0.7099(3) 0.4502(2) 0.0200(6) Uani 1 1 d . . . H3A H 1.1348 0.6701 0.4860 0.024 Uiso 1 1 calc R . . C4 C 1.0952(4) 0.7709(3) 0.3445(3) 0.0202(6) Uani 1 1 d . . . C5 C 0.9731(4) 0.8347(4) 0.2889(3) 0.0281(7) Uani 1 1 d . . . H5 H 1.0069 0.8764 0.2181 0.034 Uiso 1 1 calc R . . C6 C 0.7989(4) 0.8347(4) 0.3418(3) 0.0281(7) Uani 1 1 d . . . H6 H 0.7144 0.8785 0.3062 0.034 Uiso 1 1 calc R . . C7 C 0.7487(4) 0.7701(3) 0.4473(3) 0.0211(6) Uani 1 1 d . . . C8 C 0.5577(4) 0.7623(3) 0.4945(3) 0.0235(7) Uani 1 1 d . . . C9 C 1.5094(3) 0.8233(3) 0.1551(2) 0.0165(6) Uani 1 1 d . . . C10 C 1.3561(4) 0.8619(3) 0.2377(2) 0.0195(6) Uani 1 1 d . . . C11 C 1.3071(4) 1.0000(4) 0.2642(3) 0.0284(7) Uani 1 1 d . . . H11A H 1.2044 1.0248 0.3164 0.034 Uiso 1 1 calc R . . C12 C 1.4140(4) 1.1050(3) 0.2117(3) 0.0260(7) Uani 1 1 d . . . H12A H 1.3804 1.1991 0.2295 0.031 Uiso 1 1 calc R . . C13 C 1.5653(4) 1.0709(3) 0.1354(3) 0.0186(6) Uani 1 1 d . . . C14 C 1.6165(3) 0.9289(3) 0.1020(2) 0.0176(6) Uani 1 1 d . . . C15 C 1.7671(4) 0.8850(3) 0.0210(3) 0.0245(7) Uani 1 1 d . . . H15 H 1.8430 0.9497 -0.0142 0.029 Uiso 1 1 calc R . . C16 C 1.8011(5) 0.7470(4) -0.0055(3) 0.0329(8) Uani 1 1 d . . . H16 H 1.8978 0.7185 -0.0606 0.040 Uiso 1 1 calc R . . C17 C 1.6896(4) 0.6495(3) 0.0507(3) 0.0285(7) Uani 1 1 d . . . H17 H 1.7142 0.5562 0.0315 0.034 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 0.0166(2) 0.0159(2) 0.0230(3) 0.00213(16) -0.00222(17) -0.00976(15) S1 0.0173(4) 0.0126(4) 0.0263(4) 0.0000(3) -0.0024(3) -0.0079(3) O1 0.0171(10) 0.0275(12) 0.0251(12) 0.0066(9) -0.0026(9) -0.0131(8) O2 0.0283(12) 0.0532(16) 0.0280(13) 0.0120(11) -0.0113(10) -0.0252(11) O3 0.0197(11) 0.0320(13) 0.0408(15) -0.0089(11) 0.0032(10) -0.0073(9) O4 0.0227(12) 0.0639(19) 0.0420(16) -0.0196(14) -0.0048(11) -0.0167(12) O5 0.0158(10) 0.0175(10) 0.0316(13) 0.0013(9) 0.0073(9) -0.0084(8) O6 0.0276(12) 0.0153(11) 0.0515(16) -0.0081(11) 0.0014(11) -0.0082(9) O7 0.0351(13) 0.0257(12) 0.0240(12) 0.0052(9) -0.0050(10) -0.0138(10) O8 0.0203(11) 0.0298(12) 0.0355(14) -0.0007(10) -0.0086(10) -0.0097(9) O1w 0.0238(11) 0.0284(12) 0.0336(14) -0.0015(10) -0.0089(10) -0.0101(9) O2w 0.0277(11) 0.0226(11) 0.0268(12) 0.0054(9) -0.0082(10) -0.0124(9) O3w 0.0288(13) 0.071(2) 0.0396(16) -0.0204(14) -0.0010(12) -0.0229(13) N1 0.0169(11) 0.0155(12) 0.0220(13) -0.0020(10) 0.0012(10) -0.0078(9) C1 0.0165(13) 0.0179(14) 0.0196(15) -0.0006(11) -0.0006(11) -0.0066(10) C2 0.0163(13) 0.0176(13) 0.0201(15) -0.0007(11) -0.0008(11) -0.0087(10) C3 0.0155(13) 0.0211(14) 0.0231(16) 0.0008(11) -0.0036(11) -0.0077(10) C4 0.0125(12) 0.0195(14) 0.0250(16) -0.0015(11) 0.0033(11) -0.0077(10) C5 0.0263(16) 0.0304(17) 0.0244(17) 0.0056(13) -0.0031(13) -0.0102(13) C6 0.0223(15) 0.0332(18) 0.0271(17) 0.0058(13) -0.0079(13) -0.0063(13) C7 0.0149(13) 0.0232(15) 0.0244(16) -0.0011(12) -0.0030(12) -0.0059(11) C8 0.0155(14) 0.0301(17) 0.0233(16) 0.0026(13) -0.0053(12) -0.0046(12) C9 0.0150(12) 0.0138(13) 0.0209(15) -0.0006(10) -0.0031(11) -0.0067(10) C10 0.0162(13) 0.0169(14) 0.0240(16) 0.0017(11) -0.0015(11) -0.0086(10) C11 0.0192(14) 0.0225(16) 0.0364(19) -0.0082(14) 0.0088(13) -0.0071(12) C12 0.0236(15) 0.0158(14) 0.0355(19) -0.0057(13) 0.0009(13) -0.0066(11) C13 0.0149(13) 0.0137(13) 0.0258(16) 0.0004(11) -0.0018(12) -0.0068(10) C14 0.0156(13) 0.0151(13) 0.0227(15) 0.0007(11) -0.0043(11) -0.0077(10) C15 0.0201(14) 0.0170(14) 0.0319(17) -0.0013(12) 0.0034(12) -0.0089(11) C16 0.0296(17) 0.0217(16) 0.037(2) -0.0087(14) 0.0141(15) -0.0107(13) C17 0.0280(16) 0.0173(15) 0.0345(19) -0.0058(13) 0.0059(14) -0.0092(12) 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 O1 1.937(2) . ? Cu1 O2w 1.973(2) . ? Cu1 O1w 1.989(2) . ? Cu1 N1 2.003(3) 2_766 ? Cu1 O6 2.390(2) 2_776 ? Cu1 O5 2.396(2) 2_766 ? S1 O6 1.448(2) . ? S1 O8 1.456(2) . ? S1 O7 1.458(2) . ? S1 C13 1.781(3) . ? O1 C1 1.266(3) . ? O2 C1 1.243(4) . ? O3 C8 1.303(4) . ? O3 H3 0.8399 . ? O4 C8 1.217(4) . ? O5 C10 1.370(3) . ? O5 C4 1.402(3) . ? O5 Cu1 2.396(2) 2_766 ? O6 Cu1 2.390(2) 2_776 ? O1w H11 0.8400 . ? O1w H12 0.8400 . ? O2w H22 0.8400 . ? O2w H21 0.8400 . ? O3w H31 0.8400 . ? O3w H32 0.8400 . ? N1 C17 1.319(4) . ? N1 C9 1.377(4) . ? N1 Cu1 2.003(2) 2_766 ? C1 C2 1.505(4) . ? C2 C3 1.394(4) . ? C2 C7 1.398(4) . ? C3 C4 1.380(4) . ? C3 H3A 0.9300 . ? C4 C5 1.381(4) . ? C5 C6 1.386(4) . ? C5 H5 0.9300 . ? C6 C7 1.391(5) . ? C6 H6 0.9300 . ? C7 C8 1.509(4) . ? C9 C14 1.420(4) . ? C9 C10 1.424(4) . ? C10 C11 1.366(4) . ? C11 C12 1.414(4) . ? C11 H11A 0.9300 . ? C12 C13 1.362(4) . ? C12 H12A 0.9300 . ? C13 C14 1.434(4) . ? C14 C15 1.411(4) . ? C15 C16 1.368(4) . ? C15 H15 0.9300 . ? C16 C17 1.395(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? 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 O1 Cu1 O2w 93.42(9) . . ? O1 Cu1 O1w 87.26(9) . . ? O2w Cu1 O1w 176.47(9) . . ? O1 Cu1 N1 164.02(10) . 2_766 ? O2w Cu1 N1 94.85(10) . 2_766 ? O1w Cu1 N1 85.33(10) . 2_766 ? O1 Cu1 O6 98.16(9) . 2_776 ? O2w Cu1 O6 88.08(9) . 2_776 ? O1w Cu1 O6 88.40(9) . 2_776 ? N1 Cu1 O6 95.77(9) 2_766 2_776 ? O1 Cu1 O5 93.19(9) . 2_766 ? O2w Cu1 O5 86.77(9) . 2_766 ? O1w Cu1 O5 96.65(9) . 2_766 ? N1 Cu1 O5 73.68(9) 2_766 2_766 ? O6 Cu1 O5 167.80(9) 2_776 2_766 ? O6 S1 O8 112.84(15) . . ? O6 S1 O7 113.20(15) . . ? O8 S1 O7 112.05(14) . . ? O6 S1 C13 106.15(13) . . ? O8 S1 C13 103.85(14) . . ? O7 S1 C13 108.00(14) . . ? C1 O1 Cu1 133.5(2) . . ? C8 O3 H3 119.8 . . ? C10 O5 C4 121.1(2) . . ? C10 O5 Cu1 110.39(17) . 2_766 ? C4 O5 Cu1 125.62(17) . 2_766 ? S1 O6 Cu1 170.55(17) . 2_776 ? Cu1 O1w H11 109.5 . . ? Cu1 O1w H12 109.5 . . ? H11 O1w H12 109.5 . . ? Cu1 O2w H22 109.6 . . ? Cu1 O2w H21 109.4 . . ? H22 O2w H21 109.5 . . ? H31 O3w H32 111.8 . . ? C17 N1 C9 118.7(3) . . ? C17 N1 Cu1 119.3(2) . 2_766 ? C9 N1 Cu1 120.57(19) . 2_766 ? O2 C1 O1 125.2(3) . . ? O2 C1 C2 119.7(3) . . ? O1 C1 C2 115.1(3) . . ? C3 C2 C7 119.2(3) . . ? C3 C2 C1 119.0(3) . . ? C7 C2 C1 121.6(3) . . ? C4 C3 C2 119.3(3) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 122.4(3) . . ? C3 C4 O5 116.6(3) . . ? C5 C4 O5 120.4(3) . . ? C4 C5 C6 118.1(3) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C5 C6 C7 120.9(3) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C2 120.0(3) . . ? C6 C7 C8 117.1(3) . . ? C2 C7 C8 122.8(3) . . ? O4 C8 O3 123.6(3) . . ? O4 C8 C7 121.5(3) . . ? O3 C8 C7 114.8(3) . . ? N1 C9 C14 121.7(2) . . ? N1 C9 C10 118.9(2) . . ? C14 C9 C10 119.5(2) . . ? C11 C10 O5 124.4(3) . . ? C11 C10 C9 121.1(3) . . ? O5 C10 C9 114.3(2) . . ? C10 C11 C12 119.4(3) . . ? C10 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12A 119.4 . . ? C11 C12 H12A 119.4 . . ? C12 C13 C14 120.8(3) . . ? C12 C13 S1 118.2(2) . . ? C14 C13 S1 120.5(2) . . ? C15 C14 C9 117.2(3) . . ? C15 C14 C13 124.9(3) . . ? C9 C14 C13 117.8(2) . . ? C16 C15 C14 119.8(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 119.5(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? N1 C17 C16 123.0(3) . . ? N1 C17 H17 118.5 . . ? C16 C17 H17 118.5 . . ? 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 O2w Cu1 O1 C1 8.2(3) . . . . ? O1w Cu1 O1 C1 -175.3(3) . . . . ? N1 Cu1 O1 C1 -112.9(4) 2_766 . . . ? O6 Cu1 O1 C1 96.7(3) 2_776 . . . ? O5 Cu1 O1 C1 -78.8(3) 2_766 . . . ? O7 S1 O6 Cu1 157.7(10) . . . 2_776 ? C13 S1 O6 Cu1 39.4(10) . . . 2_776 ? Cu1 O1 C1 O2 -6.9(5) . . . . ? Cu1 O1 C1 C2 173.1(2) . . . . ? O2 C1 C2 C3 24.0(4) . . . . ? O1 C1 C2 C3 -156.0(3) . . . . ? O2 C1 C2 C7 -159.9(3) . . . . ? O1 C1 C2 C7 20.1(4) . . . . ? C7 C2 C3 C4 -0.4(4) . . . . ? C1 C2 C3 C4 175.7(3) . . . . ? C2 C3 C4 C5 1.7(5) . . . . ? C2 C3 C4 O5 -169.9(3) . . . . ? C10 O5 C4 C3 -127.9(3) . . . . ? Cu1 O5 C4 C3 73.2(3) 2_766 . . . ? C10 O5 C4 C5 60.3(4) . . . . ? Cu1 O5 C4 C5 -98.6(3) 2_766 . . . ? C3 C4 C5 C6 -1.0(5) . . . . ? O5 C4 C5 C6 170.3(3) . . . . ? C4 C5 C6 C7 -1.1(5) . . . . ? C5 C6 C7 C2 2.4(5) . . . . ? C5 C6 C7 C8 -174.1(3) . . . . ? C3 C2 C7 C6 -1.6(5) . . . . ? C1 C2 C7 C6 -177.7(3) . . . . ? C3 C2 C7 C8 174.6(3) . . . . ? C1 C2 C7 C8 -1.4(5) . . . . ? C6 C7 C8 O4 68.4(4) . . . . ? C2 C7 C8 O4 -108.0(4) . . . . ? C6 C7 C8 O3 -107.9(3) . . . . ? C2 C7 C8 O3 75.7(4) . . . . ? C17 N1 C9 C14 -3.3(4) . . . . ? Cu1 N1 C9 C14 162.9(2) 2_766 . . . ? C17 N1 C9 C10 177.6(3) . . . . ? Cu1 N1 C9 C10 -16.2(4) 2_766 . . . ? C4 O5 C10 C11 27.6(5) . . . . ? Cu1 O5 C10 C11 -170.6(3) 2_766 . . . ? C4 O5 C10 C9 -156.7(3) . . . . ? Cu1 O5 C10 C9 5.0(3) 2_766 . . . ? N1 C9 C10 C11 -178.6(3) . . . . ? C14 C9 C10 C11 2.2(5) . . . . ? N1 C9 C10 O5 5.6(4) . . . . ? C14 C9 C10 O5 -173.6(3) . . . . ? O5 C10 C11 C12 172.9(3) . . . . ? C9 C10 C11 C12 -2.5(5) . . . . ? C10 C11 C12 C13 -0.3(6) . . . . ? C11 C12 C13 C14 3.3(5) . . . . ? C11 C12 C13 S1 -169.2(3) . . . . ? O6 S1 C13 C12 -10.9(3) . . . . ? O8 S1 C13 C12 108.3(3) . . . . ? O7 S1 C13 C12 -132.6(3) . . . . ? O6 S1 C13 C14 176.7(3) . . . . ? O8 S1 C13 C14 -64.1(3) . . . . ? O7 S1 C13 C14 55.0(3) . . . . ? N1 C9 C14 C15 0.7(4) . . . . ? C10 C9 C14 C15 179.8(3) . . . . ? N1 C9 C14 C13 -178.4(3) . . . . ? C10 C9 C14 C13 0.7(4) . . . . ? C12 C13 C14 C15 177.6(3) . . . . ? S1 C13 C14 C15 -10.2(4) . . . . ? C12 C13 C14 C9 -3.4(5) . . . . ? S1 C13 C14 C9 168.8(2) . . . . ? C9 C14 C15 C16 2.1(5) . . . . ? C13 C14 C15 C16 -178.8(3) . . . . ? C14 C15 C16 C17 -2.4(6) . . . . ? C9 N1 C17 C16 3.1(5) . . . . ? Cu1 N1 C17 C16 -163.3(3) 2_766 . . . ? C15 C16 C17 N1 -0.3(6) . . . . ? 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 O3 H3 O3w 0.84 1.86 2.652(3) 156 . O1w H11 O4 0.84 1.92 2.721(3) 158 2_666 O1w H12 O3w 0.84 2.03 2.862(4) 169 . O2w H21 O2 0.84 1.93 2.698(3) 151 . O2w H22 O7 0.84 1.90 2.701(3) 158 1_446 O3w H31 O2 0.84 2.21 2.717(3) 118 1_455 O3w H32 O8 0.84 1.97 2.728(3) 150 2_776 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 1.323 _refine_diff_density_min -1.734 _refine_diff_density_rms 0.152 data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2[Cu (C10 H8 N2) (C17 H9 N O8 S)], 2[Cu (H2 O) (C10 H8 N2)], 2(H2 O)' _chemical_formula_sum 'C64 H50 Cu4 N10 O20 S2' _chemical_formula_weight 1569.40 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8222(11) _cell_length_b 11.0221(11) _cell_length_c 12.8735(12) _cell_angle_alpha 88.851(2) _cell_angle_beta 77.519(2) _cell_angle_gamma 84.557(2) _cell_volume 1492.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2200 _cell_measurement_theta_min 2.2411 _cell_measurement_theta_max 26.6624 _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 798 _exptl_absorpt_coefficient_mu 1.565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6325 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _diffrn_ambient_temperature 296(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 SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9139 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6597 _reflns_number_gt 4114 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'APEX2 (Bruker, 2009)' _computing_data_reduction 'APEX2 (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.0623P)^2^] 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 6597 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _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 Cu1 Cu 0.75254(5) 1.07418(5) 0.67442(4) 0.04444(17) Uani 1 1 d . . . Cu2 Cu 0.56093(5) 1.31352(5) 0.03199(4) 0.05260(18) Uani 1 1 d . . . S1 S 0.52740(9) 1.02792(10) 0.21132(8) 0.0393(3) Uani 1 1 d . . . O1 O 0.7713(4) 0.4043(3) 0.6827(3) 0.0752(11) Uani 1 1 d . . . O2 O 0.6336(4) 0.5520(4) 0.6528(4) 0.1129(18) Uani 1 1 d . . . O3 O 0.9909(4) 0.3638(3) 0.6794(3) 0.0746(11) Uani 1 1 d . . . O4 O 1.1552(4) 0.4647(4) 0.6675(4) 0.1054(16) Uani 1 1 d . . . H1 H 0.8810 0.3838 0.6810 0.100 Uiso 1 1 d . . . O5 O 0.8356(2) 0.9183(2) 0.5349(2) 0.0407(6) Uani 1 1 d . . . O6 O 0.3972(2) 1.0594(3) 0.2668(2) 0.0474(7) Uani 1 1 d . . . O7 O 0.5834(3) 1.1302(3) 0.1549(2) 0.0494(7) Uani 1 1 d . . . O8 O 0.5451(3) 0.9195(3) 0.1467(2) 0.0637(9) Uani 1 1 d . . . O1w O 0.6047(4) 1.2689(5) -0.1653(4) 0.1253(17) Uani 1 1 d . . . H11 H 0.6484 1.2941 -0.2223 0.188 Uiso 1 1 d R . . H12 H 0.5666 1.2103 -0.1791 0.188 Uiso 1 1 d R . . O2w O 0.4117(4) 0.4351(4) 0.7073(3) 0.1073(15) Uani 1 1 d . . . H21 H 0.4675 0.4822 0.6826 0.161 Uiso 1 1 d R . . H22 H 0.3448 0.4589 0.6868 0.161 Uiso 1 1 d R . . N1 N 0.6894(3) 1.1277(3) 0.5509(2) 0.0339(7) Uani 1 1 d . . . N2 N 0.8400(3) 1.0508(3) 0.7883(2) 0.0399(8) Uani 1 1 d . . . N3 N 0.3845(3) 1.3233(3) 0.0351(3) 0.0438(8) Uani 1 1 d . . . N4 N -0.2660(3) 1.3264(3) 0.0320(3) 0.0390(8) Uani 1 1 d . . . C1 C 0.7415(5) 0.5128(5) 0.6549(4) 0.0621(13) Uani 1 1 d . . . C2 C 0.8485(4) 0.5975(4) 0.6218(3) 0.0411(10) Uani 1 1 d . . . C3 C 0.8029(4) 0.7120(4) 0.5905(3) 0.0400(9) Uani 1 1 d . . . H3 H 0.7169 0.7278 0.5907 0.048 Uiso 1 1 calc R . . C4 C 0.8821(3) 0.8008(4) 0.5598(3) 0.0367(9) Uani 1 1 d . . . C5 C 1.0079(4) 0.7816(4) 0.5594(3) 0.0446(10) Uani 1 1 d . . . H5 H 1.0619 0.8425 0.5382 0.054 Uiso 1 1 calc R . . C6 C 1.0538(4) 0.6678(4) 0.5919(3) 0.0494(11) Uani 1 1 d . . . H6 H 1.1399 0.6535 0.5919 0.059 Uiso 1 1 calc R . . C7 C 0.9763(4) 0.5761(4) 0.6238(3) 0.0439(10) Uani 1 1 d . . . C8 C 1.0477(5) 0.4607(5) 0.6588(4) 0.0591(13) Uani 1 1 d . . . C9 C 0.6867(3) 1.0495(3) 0.4696(3) 0.0296(8) Uani 1 1 d . . . C10 C 0.7570(3) 0.9340(3) 0.4641(3) 0.0336(9) Uani 1 1 d . . . C11 C 0.7510(4) 0.8505(4) 0.3895(3) 0.0405(9) Uani 1 1 d . . . H11A H 0.7961 0.7742 0.3882 0.049 Uiso 1 1 calc R . . C12 C 0.6771(4) 0.8800(3) 0.3152(3) 0.0390(9) Uani 1 1 d . . . H12A H 0.6711 0.8217 0.2657 0.047 Uiso 1 1 calc R . . C13 C 0.6128(3) 0.9930(3) 0.3134(3) 0.0327(8) Uani 1 1 d . . . C14 C 0.6170(3) 1.0817(3) 0.3907(3) 0.0306(8) Uani 1 1 d . . . C15 C 0.5541(3) 1.2007(3) 0.3949(3) 0.0378(9) Uani 1 1 d . . . H15 H 0.5091 1.2262 0.3432 0.045 Uiso 1 1 calc R . . C16 C 0.5598(4) 1.2770(4) 0.4744(3) 0.0445(10) Uani 1 1 d . . . H16 H 0.5193 1.3555 0.4775 0.053 Uiso 1 1 calc R . . C17 C 0.6266(4) 1.2372(4) 0.5510(3) 0.0429(10) Uani 1 1 d . . . H17 H 0.6274 1.2905 0.6059 0.052 Uiso 1 1 calc R . . C18 C 0.9662(4) 1.0452(5) 0.7724(3) 0.0587(13) Uani 1 1 d . . . H18 H 1.0126 1.0560 0.7037 0.070 Uiso 1 1 calc R . . C19 C 1.0302(4) 1.0244(5) 0.8516(3) 0.0592(13) Uani 1 1 d . . . H19 H 1.1185 1.0198 0.8357 0.071 Uiso 1 1 calc R . . C20 C 0.9664(3) 1.0101(3) 0.9556(3) 0.0343(9) Uani 1 1 d . . . C21 C 0.8365(4) 1.0159(4) 0.9715(3) 0.0416(10) Uani 1 1 d . . . H21A H 0.7880 1.0062 1.0397 0.050 Uiso 1 1 calc R . . C22 C 0.7775(4) 1.0361(4) 0.8879(3) 0.0445(10) Uani 1 1 d . . . H22A H 0.6893 1.0396 0.9015 0.053 Uiso 1 1 calc R . . C23 C 0.3386(4) 1.3641(4) -0.0487(3) 0.0493(11) Uani 1 1 d . . . H23 H 0.3946 1.3929 -0.1072 0.059 Uiso 1 1 calc R . . C24 C 0.2144(4) 1.3656(4) -0.0525(3) 0.0455(11) Uani 1 1 d . . . H24 H 0.1874 1.3938 -0.1133 0.055 Uiso 1 1 calc R . . C25 C 0.1281(3) 1.3258(3) 0.0326(3) 0.0324(8) Uani 1 1 d . . . C26 C 0.1763(3) 1.2843(4) 0.1201(3) 0.0432(10) Uani 1 1 d . . . H26 H 0.1221 1.2562 0.1801 0.052 Uiso 1 1 calc R . . C27 C 0.3025(4) 1.2846(4) 0.1183(3) 0.0460(10) Uani 1 1 d . . . H27 H 0.3324 1.2566 0.1777 0.055 Uiso 1 1 calc R . . C28 C -0.1790(4) 1.3365(4) -0.0584(3) 0.0430(10) Uani 1 1 d . . . H28 H -0.2062 1.3432 -0.1222 0.052 Uiso 1 1 calc R . . C29 C -0.0518(4) 1.3375(4) -0.0611(3) 0.0410(10) Uani 1 1 d . . . H29 H 0.0052 1.3451 -0.1257 0.049 Uiso 1 1 calc R . . C30 C -0.0081(3) 1.3271(3) 0.0327(3) 0.0331(8) Uani 1 1 d . . . C31 C -0.1003(4) 1.3205(4) 0.1254(3) 0.0419(10) Uani 1 1 d . . . H31 H -0.0766 1.3169 0.1908 0.050 Uiso 1 1 calc R . . C32 C -0.2261(4) 1.3192(4) 0.1220(3) 0.0464(10) Uani 1 1 d . . . H32 H -0.2854 1.3129 0.1855 0.056 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 0.0435(3) 0.0585(4) 0.0375(3) 0.0049(2) -0.0228(2) -0.0046(2) Cu2 0.0244(3) 0.0713(4) 0.0652(4) -0.0068(3) -0.0159(2) -0.0045(2) S1 0.0369(5) 0.0498(6) 0.0361(5) 0.0046(5) -0.0177(4) -0.0075(5) O1 0.103(3) 0.053(2) 0.078(2) 0.0193(18) -0.033(2) -0.019(2) O2 0.069(3) 0.090(3) 0.200(5) 0.064(3) -0.067(3) -0.036(2) O3 0.103(3) 0.054(2) 0.061(2) 0.0102(17) -0.017(2) 0.017(2) O4 0.096(3) 0.076(3) 0.163(4) -0.006(3) -0.085(3) 0.029(2) O5 0.0391(15) 0.0394(16) 0.0494(16) 0.0062(12) -0.0240(13) -0.0005(12) O6 0.0295(14) 0.064(2) 0.0533(18) 0.0141(14) -0.0177(13) -0.0099(13) O7 0.0440(17) 0.064(2) 0.0449(17) 0.0203(14) -0.0171(13) -0.0146(14) O8 0.082(2) 0.063(2) 0.056(2) -0.0156(16) -0.0399(18) 0.0023(17) O1w 0.086(3) 0.160(5) 0.129(4) -0.003(3) -0.018(3) -0.016(3) O2w 0.083(3) 0.140(4) 0.097(3) 0.040(3) -0.016(2) -0.015(3) N1 0.0342(17) 0.0387(19) 0.0328(17) 0.0024(14) -0.0158(13) -0.0048(14) N2 0.0361(18) 0.052(2) 0.0369(19) 0.0027(15) -0.0194(15) -0.0051(15) N3 0.0239(16) 0.061(2) 0.049(2) 0.0013(17) -0.0134(15) -0.0045(15) N4 0.0234(16) 0.049(2) 0.047(2) 0.0054(16) -0.0112(14) -0.0069(14) C1 0.074(4) 0.059(3) 0.063(3) 0.014(3) -0.031(3) -0.021(3) C2 0.053(3) 0.040(2) 0.033(2) 0.0011(17) -0.0174(18) -0.0022(19) C3 0.036(2) 0.046(2) 0.041(2) 0.0037(18) -0.0175(18) 0.0031(18) C4 0.031(2) 0.042(2) 0.038(2) 0.0054(18) -0.0147(16) 0.0063(17) C5 0.035(2) 0.058(3) 0.042(2) 0.008(2) -0.0123(18) -0.001(2) C6 0.034(2) 0.064(3) 0.049(3) -0.002(2) -0.0176(19) 0.019(2) C7 0.053(3) 0.046(3) 0.034(2) -0.0027(18) -0.0170(19) 0.007(2) C8 0.073(4) 0.053(3) 0.053(3) -0.014(2) -0.028(3) 0.023(3) C9 0.0230(17) 0.035(2) 0.0315(19) 0.0045(16) -0.0063(15) -0.0059(15) C10 0.0260(19) 0.039(2) 0.037(2) 0.0087(17) -0.0125(15) 0.0014(16) C11 0.042(2) 0.036(2) 0.044(2) 0.0030(18) -0.0153(18) 0.0048(18) C12 0.043(2) 0.037(2) 0.040(2) -0.0026(17) -0.0146(18) -0.0007(18) C13 0.0314(19) 0.039(2) 0.0300(19) 0.0050(16) -0.0114(15) -0.0031(16) C14 0.0243(18) 0.038(2) 0.0298(19) 0.0045(16) -0.0076(14) -0.0039(15) C15 0.033(2) 0.044(2) 0.038(2) 0.0061(18) -0.0161(17) 0.0036(17) C16 0.050(3) 0.038(2) 0.046(2) 0.0021(19) -0.017(2) 0.0089(19) C17 0.048(2) 0.041(2) 0.043(2) -0.0029(19) -0.0172(19) -0.0028(19) C18 0.039(2) 0.108(4) 0.034(2) 0.011(2) -0.0150(19) -0.014(2) C19 0.029(2) 0.116(4) 0.036(2) 0.007(2) -0.0117(18) -0.017(2) C20 0.030(2) 0.042(2) 0.032(2) 0.0001(17) -0.0120(16) -0.0008(17) C21 0.030(2) 0.064(3) 0.032(2) 0.0032(19) -0.0105(16) -0.0053(19) C22 0.027(2) 0.067(3) 0.043(2) -0.001(2) -0.0144(18) -0.0064(19) C23 0.031(2) 0.068(3) 0.050(3) 0.017(2) -0.0090(19) -0.011(2) C24 0.029(2) 0.066(3) 0.044(2) 0.020(2) -0.0118(17) -0.0082(19) C25 0.0248(18) 0.034(2) 0.041(2) -0.0005(17) -0.0131(16) 0.0000(15) C26 0.0216(18) 0.065(3) 0.042(2) 0.010(2) -0.0069(16) -0.0027(18) C27 0.027(2) 0.067(3) 0.045(2) 0.005(2) -0.0134(18) -0.0005(19) C28 0.035(2) 0.053(3) 0.045(2) 0.005(2) -0.0190(19) -0.0056(19) C29 0.026(2) 0.055(3) 0.041(2) 0.0041(19) -0.0062(17) -0.0066(18) C30 0.0253(19) 0.035(2) 0.041(2) 0.0006(17) -0.0117(16) -0.0025(15) C31 0.030(2) 0.064(3) 0.035(2) -0.0016(19) -0.0123(16) -0.0082(19) C32 0.031(2) 0.065(3) 0.044(2) 0.000(2) -0.0064(18) -0.0102(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.910(3) . ? Cu1 N1 1.923(3) . ? Cu1 O6 2.290(3) 2_676 ? Cu1 O5 2.474(3) . ? Cu2 N4 1.892(3) 1_655 ? Cu2 N3 1.894(3) . ? Cu2 O1w 2.531(5) . ? Cu2 O7 2.567(3) . ? S1 O7 1.439(3) . ? S1 O8 1.443(3) . ? S1 O6 1.449(3) . ? S1 C13 1.779(4) . ? O1 C1 1.273(6) . ? O2 C1 1.212(6) . ? O3 C8 1.277(6) . ? O4 C8 1.198(6) . ? O5 C10 1.373(4) . ? O5 C4 1.400(4) . ? O6 Cu1 2.290(3) 2_676 ? O1w H11 0.8400 . ? O1w H12 0.8401 . ? O2w H21 0.8400 . ? O2w H22 0.8401 . ? N1 C17 1.328(5) . ? N1 C9 1.377(4) . ? N2 C22 1.328(5) . ? N2 C18 1.332(5) . ? N3 C27 1.326(5) . ? N3 C23 1.334(5) . ? N4 C32 1.319(5) . ? N4 C28 1.339(5) . ? N4 Cu2 1.892(3) 1_455 ? C1 C2 1.539(6) . ? C2 C7 1.387(6) . ? C2 C3 1.396(5) . ? C3 C4 1.359(5) . ? C3 H3 0.9300 . ? C4 C5 1.358(5) . ? C5 C6 1.395(5) . ? C5 H5 0.9300 . ? C6 C7 1.374(6) . ? C6 H6 0.9300 . ? C7 C8 1.536(6) . ? C9 C14 1.411(5) . ? C9 C10 1.415(5) . ? C10 C11 1.359(5) . ? C11 C12 1.389(5) . ? C11 H11A 0.9300 . ? C12 C13 1.371(5) . ? C12 H12A 0.9300 . ? C13 C14 1.419(5) . ? C14 C15 1.415(5) . ? C15 C16 1.353(5) . ? C15 H15 0.9300 . ? C16 C17 1.385(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.356(5) . ? C18 H18 0.9300 . ? C19 C20 1.380(5) . ? C19 H19 0.9300 . ? C20 C21 1.372(5) . ? C20 C20 1.485(7) 2_777 ? C21 C22 1.370(5) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 C24 1.355(5) . ? C23 H23 0.9300 . ? C24 C25 1.372(5) . ? C24 H24 0.9300 . ? C25 C26 1.392(5) . ? C25 C30 1.473(5) . ? C26 C27 1.361(5) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.371(5) . ? C28 H28 0.9300 . ? C29 C30 1.388(5) . ? C29 H29 0.9300 . ? C30 C31 1.386(5) . ? C31 C32 1.373(5) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 166.74(13) . . ? N2 Cu1 O6 97.13(12) . 2_676 ? N1 Cu1 O6 95.99(11) . 2_676 ? N2 Cu1 O5 110.31(12) . . ? N1 Cu1 O5 73.14(11) . . ? O6 Cu1 O5 83.36(10) 2_676 . ? N4 Cu2 N3 172.35(15) 1_655 . ? N4 Cu2 O1w 93.57(15) 1_655 . ? N3 Cu2 O1w 89.03(15) . . ? N4 Cu2 O7 84.61(12) 1_655 . ? N3 Cu2 O7 100.66(12) . . ? O1w Cu2 O7 116.47(14) . . ? O7 S1 O8 113.09(19) . . ? O7 S1 O6 112.16(18) . . ? O8 S1 O6 114.06(19) . . ? O7 S1 C13 105.61(17) . . ? O8 S1 C13 105.92(18) . . ? O6 S1 C13 105.07(17) . . ? C10 O5 C4 120.1(3) . . ? C10 O5 Cu1 105.5(2) . . ? C4 O5 Cu1 121.5(2) . . ? S1 O6 Cu1 126.23(18) . 2_676 ? S1 O7 Cu2 148.08(17) . . ? Cu2 O1w H11 138.8 . . ? Cu2 O1w H12 112.3 . . ? H11 O1w H12 108.9 . . ? H21 O2w H22 108.8 . . ? C17 N1 C9 117.4(3) . . ? C17 N1 Cu1 119.4(3) . . ? C9 N1 Cu1 122.2(2) . . ? C22 N2 C18 116.3(3) . . ? C22 N2 Cu1 121.3(3) . . ? C18 N2 Cu1 122.3(3) . . ? C27 N3 C23 117.4(3) . . ? C27 N3 Cu2 121.4(3) . . ? C23 N3 Cu2 121.1(3) . . ? C32 N4 C28 117.7(3) . . ? C32 N4 Cu2 120.3(3) . 1_455 ? C28 N4 Cu2 121.9(3) . 1_455 ? O2 C1 O1 123.2(5) . . ? O2 C1 C2 118.8(4) . . ? O1 C1 C2 118.0(5) . . ? C7 C2 C3 118.9(4) . . ? C7 C2 C1 129.2(4) . . ? C3 C2 C1 111.8(4) . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 121.2(4) . . ? C5 C4 O5 117.3(4) . . ? C3 C4 O5 121.3(3) . . ? C4 C5 C6 118.0(4) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C7 C6 C5 122.3(4) . . ? C7 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C6 C7 C2 118.5(4) . . ? C6 C7 C8 112.8(4) . . ? C2 C7 C8 128.7(4) . . ? O4 C8 O3 121.7(5) . . ? O4 C8 C7 118.7(5) . . ? O3 C8 C7 119.5(5) . . ? N1 C9 C14 121.9(3) . . ? N1 C9 C10 119.0(3) . . ? C14 C9 C10 119.0(3) . . ? C11 C10 O5 124.1(3) . . ? C11 C10 C9 121.3(3) . . ? O5 C10 C9 114.4(3) . . ? C10 C11 C12 119.5(4) . . ? C10 C11 H11A 120.2 . . ? C12 C11 H11A 120.2 . . ? C13 C12 C11 121.4(4) . . ? C13 C12 H12A 119.3 . . ? C11 C12 H12A 119.3 . . ? C12 C13 C14 120.2(3) . . ? C12 C13 S1 119.1(3) . . ? C14 C13 S1 120.6(3) . . ? C9 C14 C15 117.5(3) . . ? C9 C14 C13 118.3(3) . . ? C15 C14 C13 124.2(3) . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 119.4(4) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? N1 C17 C16 124.1(4) . . ? N1 C17 H17 118.0 . . ? C16 C17 H17 118.0 . . ? N2 C18 C19 123.2(4) . . ? N2 C18 H18 118.4 . . ? C19 C18 H18 118.4 . . ? C18 C19 C20 121.1(4) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C21 C20 C19 115.5(3) . . ? C21 C20 C20 122.1(4) . 2_777 ? C19 C20 C20 122.4(4) . 2_777 ? C22 C21 C20 120.6(4) . . ? C22 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 . . ? N2 C22 C21 123.3(4) . . ? N2 C22 H22A 118.4 . . ? C21 C22 H22A 118.4 . . ? N3 C23 C24 123.1(4) . . ? N3 C23 H23 118.4 . . ? C24 C23 H23 118.4 . . ? C23 C24 C25 120.4(4) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C24 C25 C26 116.2(3) . . ? C24 C25 C30 122.4(3) . . ? C26 C25 C30 121.4(3) . . ? C27 C26 C25 120.3(4) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? N3 C27 C26 122.6(4) . . ? N3 C27 H27 118.7 . . ? C26 C27 H27 118.7 . . ? N4 C28 C29 123.0(4) . . ? N4 C28 H28 118.5 . . ? C29 C28 H28 118.5 . . ? C28 C29 C30 119.9(4) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C31 C30 C29 116.0(3) . . ? C31 C30 C25 122.6(3) . . ? C29 C30 C25 121.4(3) . . ? C32 C31 C30 120.8(4) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? N4 C32 C31 122.5(4) . . ? N4 C32 H32 118.7 . . ? C31 C32 H32 118.7 . . ? 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 Cu1 O5 C10 172.9(2) . . . . ? N1 Cu1 O5 C10 -20.6(2) . . . . ? O6 Cu1 O5 C10 77.7(2) 2_676 . . . ? N2 Cu1 O5 C4 31.6(3) . . . . ? N1 Cu1 O5 C4 -161.9(3) . . . . ? O6 Cu1 O5 C4 -63.5(3) 2_676 . . . ? O7 S1 O6 Cu1 160.56(17) . . . 2_676 ? O8 S1 O6 Cu1 30.4(3) . . . 2_676 ? C13 S1 O6 Cu1 -85.2(2) . . . 2_676 ? O8 S1 O7 Cu2 85.7(4) . . . . ? O6 S1 O7 Cu2 -45.0(4) . . . . ? C13 S1 O7 Cu2 -158.9(3) . . . . ? N4 Cu2 O7 S1 -173.5(4) 1_655 . . . ? N3 Cu2 O7 S1 12.1(4) . . . . ? O1w Cu2 O7 S1 -82.2(4) . . . . ? N2 Cu1 N1 C17 -66.2(7) . . . . ? O6 Cu1 N1 C17 105.5(3) 2_676 . . . ? O5 Cu1 N1 C17 -173.4(3) . . . . ? N2 Cu1 N1 C9 125.6(6) . . . . ? O6 Cu1 N1 C9 -62.7(3) 2_676 . . . ? O5 Cu1 N1 C9 18.5(3) . . . . ? N1 Cu1 N2 C22 133.3(6) . . . . ? O6 Cu1 N2 C22 -38.4(3) 2_676 . . . ? O5 Cu1 N2 C22 -123.9(3) . . . . ? N1 Cu1 N2 C18 -48.5(8) . . . . ? O6 Cu1 N2 C18 139.8(4) 2_676 . . . ? O5 Cu1 N2 C18 54.3(4) . . . . ? O1w Cu2 N3 C27 144.5(3) . . . . ? O7 Cu2 N3 C27 27.7(3) . . . . ? O1w Cu2 N3 C23 -32.2(4) . . . . ? O7 Cu2 N3 C23 -149.0(3) . . . . ? O2 C1 C2 C7 175.7(5) . . . . ? O1 C1 C2 C7 -4.7(7) . . . . ? O2 C1 C2 C3 -1.3(7) . . . . ? O1 C1 C2 C3 178.3(4) . . . . ? C7 C2 C3 C4 1.7(6) . . . . ? C1 C2 C3 C4 179.1(4) . . . . ? C2 C3 C4 C5 -0.7(6) . . . . ? C2 C3 C4 O5 -175.8(3) . . . . ? C10 O5 C4 C5 133.5(4) . . . . ? Cu1 O5 C4 C5 -90.6(4) . . . . ? C10 O5 C4 C3 -51.1(5) . . . . ? Cu1 O5 C4 C3 84.7(4) . . . . ? C3 C4 C5 C6 -0.1(6) . . . . ? O5 C4 C5 C6 175.2(3) . . . . ? C4 C5 C6 C7 -0.1(6) . . . . ? C5 C6 C7 C2 1.1(6) . . . . ? C5 C6 C7 C8 -178.4(4) . . . . ? C3 C2 C7 C6 -1.8(6) . . . . ? C1 C2 C7 C6 -178.7(4) . . . . ? C3 C2 C7 C8 177.6(4) . . . . ? C1 C2 C7 C8 0.7(7) . . . . ? C6 C7 C8 O4 8.7(6) . . . . ? C2 C7 C8 O4 -170.8(5) . . . . ? C6 C7 C8 O3 -172.3(4) . . . . ? C2 C7 C8 O3 8.3(7) . . . . ? C17 N1 C9 C14 -1.9(5) . . . . ? Cu1 N1 C9 C14 166.5(2) . . . . ? C17 N1 C9 C10 177.3(3) . . . . ? Cu1 N1 C9 C10 -14.3(4) . . . . ? C4 O5 C10 C11 -22.3(5) . . . . ? Cu1 O5 C10 C11 -164.3(3) . . . . ? C4 O5 C10 C9 161.8(3) . . . . ? Cu1 O5 C10 C9 19.8(3) . . . . ? N1 C9 C10 C11 175.7(3) . . . . ? C14 C9 C10 C11 -5.0(5) . . . . ? N1 C9 C10 O5 -8.2(5) . . . . ? C14 C9 C10 O5 171.0(3) . . . . ? O5 C10 C11 C12 -173.9(3) . . . . ? C9 C10 C11 C12 1.7(6) . . . . ? C10 C11 C12 C13 2.0(6) . . . . ? C11 C12 C13 C14 -2.3(6) . . . . ? C11 C12 C13 S1 176.3(3) . . . . ? O7 S1 C13 C12 -119.9(3) . . . . ? O8 S1 C13 C12 0.3(4) . . . . ? O6 S1 C13 C12 121.4(3) . . . . ? O7 S1 C13 C14 58.7(3) . . . . ? O8 S1 C13 C14 178.9(3) . . . . ? O6 S1 C13 C14 -60.0(3) . . . . ? N1 C9 C14 C15 3.0(5) . . . . ? C10 C9 C14 C15 -176.2(3) . . . . ? N1 C9 C14 C13 -176.2(3) . . . . ? C10 C9 C14 C13 4.6(5) . . . . ? C12 C13 C14 C9 -1.1(5) . . . . ? S1 C13 C14 C9 -179.7(3) . . . . ? C12 C13 C14 C15 179.8(4) . . . . ? S1 C13 C14 C15 1.2(5) . . . . ? C9 C14 C15 C16 -1.7(5) . . . . ? C13 C14 C15 C16 177.4(4) . . . . ? C14 C15 C16 C17 -0.4(6) . . . . ? C9 N1 C17 C16 -0.4(6) . . . . ? Cu1 N1 C17 C16 -169.1(3) . . . . ? C15 C16 C17 N1 1.6(7) . . . . ? C22 N2 C18 C19 0.7(7) . . . . ? Cu1 N2 C18 C19 -177.6(4) . . . . ? N2 C18 C19 C20 -1.3(8) . . . . ? C18 C19 C20 C21 1.2(7) . . . . ? C18 C19 C20 C20 -178.6(5) . . . 2_777 ? C19 C20 C21 C22 -0.6(6) . . . . ? C20 C20 C21 C22 179.2(4) 2_777 . . . ? C18 N2 C22 C21 0.0(6) . . . . ? Cu1 N2 C22 C21 178.3(3) . . . . ? C20 C21 C22 N2 0.0(7) . . . . ? C27 N3 C23 C24 -1.1(7) . . . . ? Cu2 N3 C23 C24 175.8(4) . . . . ? N3 C23 C24 C25 1.0(7) . . . . ? C23 C24 C25 C26 -0.4(6) . . . . ? C23 C24 C25 C30 179.2(4) . . . . ? C24 C25 C26 C27 0.0(6) . . . . ? C30 C25 C26 C27 -179.6(4) . . . . ? C23 N3 C27 C26 0.6(6) . . . . ? Cu2 N3 C27 C26 -176.2(3) . . . . ? C25 C26 C27 N3 -0.1(7) . . . . ? C32 N4 C28 C29 1.1(6) . . . . ? Cu2 N4 C28 C29 -175.3(3) 1_455 . . . ? N4 C28 C29 C30 0.4(6) . . . . ? C28 C29 C30 C31 -2.2(6) . . . . ? C28 C29 C30 C25 179.0(4) . . . . ? C24 C25 C30 C31 -161.4(4) . . . . ? C26 C25 C30 C31 18.3(6) . . . . ? C24 C25 C30 C29 17.3(6) . . . . ? C26 C25 C30 C29 -163.0(4) . . . . ? C29 C30 C31 C32 2.7(6) . . . . ? C25 C30 C31 C32 -178.5(4) . . . . ? C28 N4 C32 C31 -0.6(6) . . . . ? Cu2 N4 C32 C31 175.9(3) 1_455 . . . ? C30 C31 C32 N4 -1.4(7) . . . . ? 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 O1w H11 O1 0.84 2.07 2.859(6) 156 1_564 O1w H12 O8 0.84 1.94 2.730(6) 156 2_675 O2w H21 O2 0.84 1.98 2.783(6) 160 . O2w H22 O4 0.84 2.11 2.917(6) 160 1_455 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.366 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.078 data_4h _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 N O2' _chemical_formula_weight 301.33 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' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'Pbca ' 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' '-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 11.287(10) _cell_length_b 14.380(13) _cell_length_c 18.206(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2955(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4096 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 25.14 _exptl_crystal_description plate-like _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9818 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_reflns_number 13841 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2605 _reflns_number_gt 1975 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0539P)^2^+0.2665P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0083(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2605 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 O1 O 1.12401(9) 1.09975(7) 0.29165(6) 0.0525(3) Uani 1 1 d . . . C19 C 0.65610(12) 0.77171(10) 0.41400(8) 0.0456(4) Uani 1 1 d . . . C11 C 0.78709(12) 0.90062(9) 0.37332(8) 0.0417(3) Uani 1 1 d . . . C8 C 1.00143(12) 0.99032(9) 0.35335(8) 0.0423(3) Uani 1 1 d . . . C12 C 0.87365(12) 0.89765(10) 0.42604(8) 0.0468(4) Uani 1 1 d . . . H12A H 0.8599 0.8652 0.4694 0.056 Uiso 1 1 calc R . . C14 C 0.67008(12) 0.86007(10) 0.38603(8) 0.0438(4) Uani 1 1 d . . . C13 C 0.97890(13) 0.94107(10) 0.41616(8) 0.0479(4) Uani 1 1 d . . . H13A H 1.0366 0.9374 0.4525 0.057 Uiso 1 1 calc R . . N1 N 1.19552(10) 1.03963(8) 0.39426(7) 0.0495(3) Uani 1 1 d . . . C7 C 1.11027(12) 1.04104(9) 0.34830(8) 0.0442(4) Uani 1 1 d . . . C9 C 0.91659(13) 0.99253(10) 0.29966(8) 0.0506(4) Uani 1 1 d . . . H9A H 0.9309 1.0246 0.2562 0.061 Uiso 1 1 calc R . . C10 C 0.81161(13) 0.94801(10) 0.30958(8) 0.0507(4) Uani 1 1 d . . . H10A H 0.7551 0.9496 0.2724 0.061 Uiso 1 1 calc R . . C6 C 1.23065(13) 1.14084(10) 0.30538(9) 0.0490(4) Uani 1 1 d . . . C1 C 1.27498(12) 1.10378(10) 0.36802(8) 0.0482(4) Uani 1 1 d . . . C15 C 0.56990(13) 0.90977(11) 0.37144(10) 0.0578(4) Uani 1 1 d . . . H15A H 0.5772 0.9696 0.3526 0.069 Uiso 1 1 calc R . . C18 C 0.54564(13) 0.73640(11) 0.42597(9) 0.0548(4) Uani 1 1 d . . . H18A H 0.5371 0.6766 0.4446 0.066 Uiso 1 1 calc R . . C2 C 1.38160(14) 1.13372(12) 0.39510(11) 0.0653(5) Uani 1 1 d . . . H2A H 1.4135 1.1095 0.4381 0.078 Uiso 1 1 calc R . . C17 C 0.44806(14) 0.78827(12) 0.41076(10) 0.0622(5) Uani 1 1 d . . . H17A H 0.3730 0.7638 0.4192 0.075 Uiso 1 1 calc R . . C16 C 0.45937(14) 0.87481(13) 0.38355(11) 0.0666(5) Uani 1 1 d . . . H16A H 0.3926 0.9103 0.3731 0.080 Uiso 1 1 calc R . . C3 C 1.43824(16) 1.20052(13) 0.35584(13) 0.0747(6) Uani 1 1 d . . . H3A H 1.5111 1.2224 0.3723 0.090 Uiso 1 1 calc R . . C4 C 1.39157(17) 1.23631(13) 0.29326(13) 0.0779(6) Uani 1 1 d . . . H4A H 1.4335 1.2820 0.2681 0.093 Uiso 1 1 calc R . . C5 C 1.28566(16) 1.20762(12) 0.26624(10) 0.0696(5) Uani 1 1 d . . . H5A H 1.2532 1.2324 0.2236 0.083 Uiso 1 1 calc R . . O2 O 0.75713(9) 0.72413(7) 0.42597(6) 0.0569(3) Uani 1 1 d . . . C20 C 0.74899(16) 0.63287(11) 0.45128(13) 0.0776(6) Uani 1 1 d . . . H20A H 0.8271 0.6075 0.4570 0.116 Uiso 1 1 calc R . . H20B H 0.7054 0.5962 0.4165 0.116 Uiso 1 1 calc R . . H20C H 0.7088 0.6321 0.4977 0.116 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 O1 0.0494(6) 0.0530(6) 0.0549(6) 0.0071(5) 0.0024(5) -0.0043(5) C19 0.0458(8) 0.0423(8) 0.0488(8) -0.0029(7) 0.0011(7) -0.0029(7) C11 0.0434(8) 0.0340(7) 0.0475(8) -0.0007(6) 0.0011(6) 0.0022(6) C8 0.0407(7) 0.0377(7) 0.0484(8) 0.0001(7) 0.0039(6) 0.0033(6) C12 0.0509(9) 0.0425(8) 0.0471(8) 0.0086(7) -0.0006(7) -0.0038(7) C14 0.0435(8) 0.0414(8) 0.0464(8) -0.0031(6) 0.0002(6) -0.0008(6) C13 0.0471(8) 0.0456(8) 0.0510(9) 0.0061(7) -0.0068(7) -0.0020(7) N1 0.0432(7) 0.0499(7) 0.0552(7) 0.0054(6) 0.0001(6) -0.0044(6) C7 0.0436(8) 0.0393(8) 0.0495(8) 0.0007(7) 0.0068(7) 0.0025(6) C9 0.0514(9) 0.0551(9) 0.0454(8) 0.0088(7) 0.0012(7) -0.0027(7) C10 0.0481(9) 0.0546(9) 0.0495(8) 0.0071(7) -0.0068(7) -0.0032(7) C6 0.0459(8) 0.0451(8) 0.0560(9) -0.0020(7) 0.0094(7) -0.0025(7) C1 0.0439(8) 0.0444(8) 0.0563(9) -0.0024(7) 0.0067(7) -0.0004(7) C15 0.0504(9) 0.0488(9) 0.0743(11) 0.0052(8) -0.0012(8) 0.0005(7) C18 0.0552(9) 0.0492(9) 0.0601(10) -0.0015(8) 0.0041(8) -0.0111(7) C2 0.0549(10) 0.0659(11) 0.0750(11) -0.0030(9) -0.0050(9) -0.0095(9) C17 0.0470(9) 0.0666(11) 0.0732(11) -0.0045(9) 0.0051(8) -0.0127(8) C16 0.0434(9) 0.0697(12) 0.0868(13) 0.0012(10) -0.0018(9) 0.0036(8) C3 0.0565(11) 0.0663(11) 0.1013(16) -0.0124(12) 0.0039(10) -0.0180(9) C4 0.0726(13) 0.0612(11) 0.0998(16) 0.0053(11) 0.0173(11) -0.0195(10) C5 0.0715(11) 0.0635(11) 0.0736(12) 0.0131(10) 0.0126(9) -0.0110(9) O2 0.0519(6) 0.0384(6) 0.0805(8) 0.0089(5) -0.0002(5) -0.0009(5) C20 0.0712(11) 0.0423(9) 0.1193(16) 0.0153(10) -0.0173(11) -0.0068(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 O1 C7 1.3419(19) . ? O1 C6 1.364(2) . ? C19 O2 1.3476(19) . ? C19 C18 1.364(2) . ? C19 C14 1.378(2) . ? C11 C12 1.370(2) . ? C11 C10 1.374(2) . ? C11 C14 1.462(2) . ? C8 C13 1.369(2) . ? C8 C9 1.369(2) . ? C8 C7 1.432(2) . ? C12 C13 1.354(2) . ? C12 H12A 0.9300 . ? C14 C15 1.364(2) . ? C13 H13A 0.9300 . ? N1 C7 1.275(2) . ? N1 C1 1.372(2) . ? C9 C10 1.359(2) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C6 C5 1.347(2) . ? C6 C1 1.355(2) . ? C1 C2 1.370(2) . ? C15 C16 1.363(2) . ? C15 H15A 0.9300 . ? C18 C17 1.359(2) . ? C18 H18A 0.9300 . ? C2 C3 1.357(3) . ? C2 H2A 0.9300 . ? C17 C16 1.345(3) . ? C17 H17A 0.9300 . ? C16 H16A 0.9300 . ? C3 C4 1.357(3) . ? C3 H3A 0.9300 . ? C4 C5 1.357(3) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? O2 C20 1.394(2) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 C7 O1 C6 103.51(12) . . ? O2 C19 C18 123.97(14) . . ? O2 C19 C14 115.54(12) . . ? C18 C19 C14 120.47(14) . . ? C12 C11 C10 117.61(14) . . ? C12 C11 C14 121.39(13) . . ? C10 C11 C14 120.89(13) . . ? C13 C8 C9 118.60(14) . . ? C13 C8 C7 118.47(13) . . ? C9 C8 C7 122.86(14) . . ? C13 C12 C11 121.21(14) . . ? C13 C12 H12A 119.4 . . ? C11 C12 H12A 119.4 . . ? C15 C14 C19 117.41(14) . . ? C15 C14 C11 120.61(14) . . ? C19 C14 C11 121.98(12) . . ? C12 C13 C8 120.83(14) . . ? C12 C13 H13A 119.6 . . ? C8 C13 H13A 119.6 . . ? C7 N1 C1 104.72(13) . . ? N1 C7 O1 115.28(13) . . ? N1 C7 C8 126.67(14) . . ? O1 C7 C8 117.98(13) . . ? C10 C9 C8 120.28(14) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C9 C10 C11 121.44(14) . . ? C9 C10 H10A 119.3 . . ? C11 C10 H10A 119.3 . . ? C5 C6 C1 123.74(16) . . ? C5 C6 O1 128.20(16) . . ? C1 C6 O1 108.05(13) . . ? C6 C1 C2 120.25(15) . . ? C6 C1 N1 108.42(14) . . ? C2 C1 N1 131.31(16) . . ? C16 C15 C14 122.28(16) . . ? C16 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? C17 C18 C19 120.27(16) . . ? C17 C18 H18A 119.9 . . ? C19 C18 H18A 119.9 . . ? C3 C2 C1 116.53(18) . . ? C3 C2 H2A 121.7 . . ? C1 C2 H2A 121.7 . . ? C16 C17 C18 120.39(15) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? C17 C16 C15 119.19(16) . . ? C17 C16 H16A 120.4 . . ? C15 C16 H16A 120.4 . . ? C4 C3 C2 121.86(18) . . ? C4 C3 H3A 119.1 . . ? C2 C3 H3A 119.1 . . ? C3 C4 C5 122.09(18) . . ? C3 C4 H4A 119.0 . . ? C5 C4 H4A 119.0 . . ? C6 C5 C4 115.52(19) . . ? C6 C5 H5A 122.2 . . ? C4 C5 H5A 122.2 . . ? C19 O2 C20 118.41(12) . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C10 C11 C12 C13 1.0(2) . . . . ? C14 C11 C12 C13 -175.17(13) . . . . ? O2 C19 C14 C15 178.45(13) . . . . ? C18 C19 C14 C15 0.3(2) . . . . ? O2 C19 C14 C11 -2.6(2) . . . . ? C18 C19 C14 C11 179.24(14) . . . . ? C12 C11 C14 C15 130.66(16) . . . . ? C10 C11 C14 C15 -45.4(2) . . . . ? C12 C11 C14 C19 -48.3(2) . . . . ? C10 C11 C14 C19 135.66(15) . . . . ? C11 C12 C13 C8 0.8(2) . . . . ? C9 C8 C13 C12 -1.9(2) . . . . ? C7 C8 C13 C12 175.02(13) . . . . ? C1 N1 C7 O1 0.86(16) . . . . ? C1 N1 C7 C8 -175.96(14) . . . . ? C6 O1 C7 N1 -1.18(16) . . . . ? C6 O1 C7 C8 175.94(12) . . . . ? C13 C8 C7 N1 6.4(2) . . . . ? C9 C8 C7 N1 -176.85(15) . . . . ? C13 C8 C7 O1 -170.39(13) . . . . ? C9 C8 C7 O1 6.4(2) . . . . ? C13 C8 C9 C10 1.2(2) . . . . ? C7 C8 C9 C10 -175.57(14) . . . . ? C8 C9 C10 C11 0.6(2) . . . . ? C12 C11 C10 C9 -1.7(2) . . . . ? C14 C11 C10 C9 174.49(13) . . . . ? C7 O1 C6 C5 -178.15(16) . . . . ? C7 O1 C6 C1 0.97(15) . . . . ? C5 C6 C1 C2 -0.1(2) . . . . ? O1 C6 C1 C2 -179.24(13) . . . . ? C5 C6 C1 N1 178.64(15) . . . . ? O1 C6 C1 N1 -0.52(16) . . . . ? C7 N1 C1 C6 -0.18(16) . . . . ? C7 N1 C1 C2 178.35(17) . . . . ? C19 C14 C15 C16 -0.1(2) . . . . ? C11 C14 C15 C16 -179.06(16) . . . . ? O2 C19 C18 C17 -178.37(15) . . . . ? C14 C19 C18 C17 -0.3(2) . . . . ? C6 C1 C2 C3 -0.4(2) . . . . ? N1 C1 C2 C3 -178.76(16) . . . . ? C19 C18 C17 C16 0.2(3) . . . . ? C18 C17 C16 C15 0.0(3) . . . . ? C14 C15 C16 C17 -0.1(3) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C1 C6 C5 C4 0.5(3) . . . . ? O1 C6 C5 C4 179.50(16) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C18 C19 O2 C20 0.8(2) . . . . ? C14 C19 O2 C20 -177.31(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.153 _refine_diff_density_min -0.108 _refine_diff_density_rms 0.031