# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_year 2010 _journal_volume 12 _journal_page_first 1 _publ_contact_author_name 'Wang Yaoyu' _publ_contact_author_email WYAOYU@NWU.EDU.CN _publ_section_title ; Self-assembled coordination polymers of V-shaped bis(pyridyl)thiadiazole dependent upon the spacer length and flexibility of aliphatic dicarboxylate ligands ; loop_ _publ_author_name 'Wang Yaoyu.' 'Rui-Ting Liu.' 'Chen Ren.' 'Qi-Zhen Shi.' 'Gui-Lin Wen.' ; Wei-Hong Zhang ; data_xb2036m _database_code_depnum_ccdc_archive 'CCDC 738467' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H8 Cu2 N4 O8 S, 2.92(H2 O)' _chemical_formula_sum 'C16 H13.84 Cu2 N4 O10.92 S' _chemical_formula_weight 596.01 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/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 31.634(9) _cell_length_b 9.214(3) _cell_length_c 8.328(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.602(5) _cell_angle_gamma 90.00 _cell_volume 2359.2(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1055 _cell_measurement_theta_min 2.307 _cell_measurement_theta_max 23.605 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1197 _exptl_absorpt_coefficient_mu 1.953 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6451 _exptl_absorpt_correction_T_max 0.8438 _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 'Bruker APEX SMART II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6623 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2561 _reflns_number_gt 1690 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2561 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1812 _refine_ls_wR_factor_gt 0.1705 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.217133(19) 0.51239(6) 0.08576(7) 0.0260(2) Uani 1 1 d . . . S1 S -0.0031(9) 0.5138(3) 0.228(2) 0.046(3) Uani 0.50 1 d P . . N1 N 0.0276(4) 0.2632(14) 0.293(2) 0.067(4) Uani 0.50 1 d P . 1 N1A N 0.0124(4) 0.2648(14) 0.167(2) 0.065(4) Uani 0.50 1 d P . 2 N2 N 0.15689(14) 0.4655(4) 0.1068(5) 0.0293(9) Uani 1 1 d . . . O1 O 0.19606(11) 0.6992(3) -0.0209(4) 0.0294(8) Uani 1 1 d . . . O2 O 0.22410(11) 0.9080(3) -0.0846(4) 0.0306(8) Uani 1 1 d . . . O3 O 0.24309(11) 0.3300(3) 0.1841(4) 0.0284(8) Uani 1 1 d . . . O4 O 0.27597(11) 0.1233(4) 0.1452(4) 0.0315(8) Uani 1 1 d . . . C1 C 0.13206(18) 0.5766(6) 0.1413(7) 0.0409(14) Uani 1 1 d . . . H1A H 0.1422 0.6713 0.1402 0.049 Uiso 1 1 calc R . . C2 C 0.09285(19) 0.5530(7) 0.1774(8) 0.0435(14) Uani 1 1 d . . . H2A H 0.0771 0.6309 0.2042 0.052 Uiso 1 1 calc R . . C3 C 0.07633(18) 0.4143(6) 0.1745(7) 0.0398(13) Uani 1 1 d . . . C4 C 0.10120(19) 0.3029(6) 0.1393(8) 0.0504(17) Uani 1 1 d . . . H4A H 0.0912 0.2079 0.1383 0.061 Uiso 1 1 calc R . . C5 C 0.14076(18) 0.3304(6) 0.1055(8) 0.0433(14) Uani 1 1 d . . . H5A H 0.1570 0.2530 0.0808 0.052 Uiso 1 1 calc R . . C6 C 0.03419(19) 0.3868(7) 0.2144(9) 0.0516(16) Uani 1 1 d . . . C7 C 0.22700(16) 0.7792(5) -0.0313(6) 0.0266(11) Uani 1 1 d . . . C8 C 0.25563(15) 0.2372(5) 0.0941(6) 0.0256(11) Uani 1 1 d . . . O11 O 0.1453(5) 0.9465(16) 0.3234(19) 0.141(5) Uiso 0.61 1 d P A 1 O12 O 0.1515(8) 0.980(2) 0.165(3) 0.146(9) Uiso 0.39 1 d P B 2 O13 O 0.0855(8) -0.053(3) 0.001(3) 0.201(10) Uiso 0.46 1 d P . . H11A H 0.1669 0.9947 0.3489 0.242 Uiso 0.61 1 d PR C 1 H11B H 0.1385 0.9445 0.2249 0.242 Uiso 0.61 1 d PR C 1 H12A H 0.1645 0.9933 0.0951 0.242 Uiso 0.39 1 d PR C 2 H12B H 0.1699 1.0137 0.2386 0.242 Uiso 0.39 1 d PR C 2 H13A H 0.0759 -0.0063 -0.0801 0.242 Uiso 0.46 1 d PR . . H13B H 0.1101 -0.0629 -0.0066 0.242 Uiso 0.46 1 d PR . . 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 0.0269(4) 0.0221(3) 0.0317(4) 0.0025(2) 0.0125(3) 0.0009(2) S1 0.034(6) 0.0458(13) 0.065(9) 0.019(4) 0.025(7) 0.006(4) N1 0.041(8) 0.048(7) 0.130(13) 0.025(9) 0.053(9) 0.016(6) N1A 0.050(9) 0.037(6) 0.123(13) -0.011(8) 0.047(9) -0.005(5) N2 0.028(2) 0.030(2) 0.035(2) -0.0025(18) 0.0159(19) -0.0007(17) O1 0.0273(19) 0.0257(17) 0.037(2) 0.0053(15) 0.0106(16) -0.0009(14) O2 0.031(2) 0.0257(18) 0.038(2) 0.0064(15) 0.0142(16) 0.0033(14) O3 0.037(2) 0.0235(17) 0.0271(18) -0.0016(14) 0.0132(16) 0.0047(14) O4 0.040(2) 0.0271(18) 0.0285(19) 0.0030(14) 0.0114(17) 0.0092(15) C1 0.038(3) 0.029(3) 0.060(4) 0.003(3) 0.020(3) 0.003(2) C2 0.038(3) 0.037(3) 0.061(4) -0.001(3) 0.023(3) 0.007(2) C3 0.031(3) 0.043(3) 0.049(3) 0.001(3) 0.018(3) -0.001(2) C4 0.040(4) 0.033(3) 0.088(5) -0.007(3) 0.034(3) -0.007(2) C5 0.037(3) 0.029(3) 0.069(4) -0.010(3) 0.023(3) -0.002(2) C6 0.031(3) 0.051(4) 0.081(5) 0.000(3) 0.028(3) 0.001(3) C7 0.033(3) 0.025(2) 0.024(3) 0.000(2) 0.011(2) 0.003(2) C8 0.028(3) 0.023(2) 0.028(3) 0.005(2) 0.013(2) 0.0006(19) _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 O3 1.963(3) . ? Cu1 O1 1.979(3) . ? Cu1 O2 2.001(3) 7_565 ? Cu1 N2 2.002(4) . ? Cu1 O4 2.347(3) 7 ? Cu1 O4 2.425(3) 4 ? S1 S1 0.37(4) 2 ? S1 C6 1.67(2) 2 ? S1 C6 1.68(2) . ? N1 C6 1.355(14) . ? N1 N1 1.73(3) 2 ? N1A C6 1.331(14) . ? N1A N1A 1.75(3) 2 ? N2 C5 1.344(6) . ? N2 C1 1.362(6) . ? O1 C7 1.245(6) . ? O2 C7 1.262(6) . ? O2 Cu1 2.001(3) 7_565 ? O3 C8 1.262(5) . ? O4 C8 1.252(5) . ? O4 Cu1 2.347(3) 7 ? O4 Cu1 2.425(3) 4_545 ? C1 C2 1.361(8) . ? C1 H1A 0.9300 . ? C2 C3 1.379(8) . ? C2 H2A 0.9300 . ? C3 C4 1.366(8) . ? C3 C6 1.470(8) . ? C4 C5 1.369(7) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 S1 1.67(2) 2 ? C7 C7 1.524(10) 7_565 ? C8 C8 1.541(9) 7 ? O11 H11A 0.7988 . ? O11 H11B 0.7978 . ? O12 H12A 0.7956 . ? O12 H12B 0.8038 . ? O13 H13A 0.8000 . ? O13 H13B 0.8001 . ? 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 O3 Cu1 O1 174.55(14) . . ? O3 Cu1 O2 91.02(14) . 7_565 ? O1 Cu1 O2 83.93(13) . 7_565 ? O3 Cu1 N2 95.28(16) . . ? O1 Cu1 N2 90.00(15) . . ? O2 Cu1 N2 169.91(15) 7_565 . ? O3 Cu1 O4 77.04(12) . 7 ? O1 Cu1 O4 100.46(13) . 7 ? O2 Cu1 O4 85.73(13) 7_565 7 ? N2 Cu1 O4 103.34(15) . 7 ? O3 Cu1 O4 92.13(13) . 4 ? O1 Cu1 O4 89.78(13) . 4 ? O2 Cu1 O4 88.19(12) 7_565 4 ? N2 Cu1 O4 83.72(15) . 4 ? O4 Cu1 O4 167.46(14) 7 4 ? C6 S1 C6 90.1(5) 2 . ? C6 N1 N1 93.1(10) . 2 ? C6 N1A N1A 93.5(10) . 2 ? C5 N2 C1 117.4(5) . . ? C5 N2 Cu1 124.5(3) . . ? C1 N2 Cu1 117.7(4) . . ? C7 O1 Cu1 111.0(3) . . ? C7 O2 Cu1 110.8(3) . 7_565 ? C8 O3 Cu1 119.4(3) . . ? C8 O4 Cu1 107.9(3) . 7 ? C8 O4 Cu1 126.5(3) . 4_545 ? Cu1 O4 Cu1 121.83(14) 7 4_545 ? C2 C1 N2 121.8(5) . . ? C2 C1 H1A 119.1 . . ? N2 C1 H1A 119.1 . . ? C1 C2 C3 120.4(5) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.8 . . ? C4 C3 C2 117.7(5) . . ? C4 C3 C6 121.2(5) . . ? C2 C3 C6 121.0(5) . . ? C3 C4 C5 120.4(5) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? N2 C5 C4 122.2(5) . . ? N2 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? N1A C6 N1 46.0(8) . . ? N1A C6 C3 120.8(7) . . ? N1 C6 C3 120.3(7) . . ? N1A C6 S1 112.2(10) . 2 ? N1 C6 S1 106.4(9) . 2 ? C3 C6 S1 124.8(9) . 2 ? N1A C6 S1 106.5(9) . . ? N1 C6 S1 111.2(9) . . ? C3 C6 S1 125.7(8) . . ? O1 C7 O2 126.0(5) . . ? O1 C7 C7 118.0(5) . 7_565 ? O2 C7 C7 115.9(5) . 7_565 ? O4 C8 O3 125.1(4) . . ? O4 C8 C8 116.9(5) . 7 ? O3 C8 C8 118.1(5) . 7 ? H11A O11 H11B 107.2 . . ? H12A O12 H12B 95.3 . . ? H13A O13 H13B 100.1 . . ? 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 Cu1 N2 C5 -28.6(5) . . . . ? O1 Cu1 N2 C5 150.1(5) . . . . ? O2 Cu1 N2 C5 -157.0(7) 7_565 . . . ? O4 Cu1 N2 C5 49.3(5) 7 . . . ? O4 Cu1 N2 C5 -120.1(5) 4 . . . ? O3 Cu1 N2 C1 144.5(4) . . . . ? O1 Cu1 N2 C1 -36.8(4) . . . . ? O2 Cu1 N2 C1 16.1(11) 7_565 . . . ? O4 Cu1 N2 C1 -137.6(4) 7 . . . ? O4 Cu1 N2 C1 53.0(4) 4 . . . ? O2 Cu1 O1 C7 -3.5(3) 7_565 . . . ? N2 Cu1 O1 C7 168.5(3) . . . . ? O4 Cu1 O1 C7 -88.0(3) 7 . . . ? O4 Cu1 O1 C7 84.7(3) 4 . . . ? O2 Cu1 O3 C8 -77.7(4) 7_565 . . . ? N2 Cu1 O3 C8 110.2(4) . . . . ? O4 Cu1 O3 C8 7.7(3) 7 . . . ? O4 Cu1 O3 C8 -165.9(3) 4 . . . ? C5 N2 C1 C2 1.6(9) . . . . ? Cu1 N2 C1 C2 -172.0(5) . . . . ? N2 C1 C2 C3 -2.2(10) . . . . ? C1 C2 C3 C4 1.9(9) . . . . ? C1 C2 C3 C6 179.5(6) . . . . ? C2 C3 C4 C5 -1.1(9) . . . . ? C6 C3 C4 C5 -178.8(6) . . . . ? C1 N2 C5 C4 -0.8(9) . . . . ? Cu1 N2 C5 C4 172.3(5) . . . . ? C3 C4 C5 N2 0.6(10) . . . . ? N1A N1A C6 N1 46.9(11) 2 . . . ? N1A N1A C6 C3 150.8(8) 2 . . . ? N1A N1A C6 S1 -44.8(14) 2 . . 2 ? N1A N1A C6 S1 -56.9(14) 2 . . . ? N1 N1 C6 N1A -47.0(11) 2 . . . ? N1 N1 C6 C3 -152.1(8) 2 . . . ? N1 N1 C6 S1 58.3(14) 2 . . 2 ? N1 N1 C6 S1 45.9(14) 2 . . . ? C4 C3 C6 N1A -22.3(13) . . . . ? C2 C3 C6 N1A 160.2(10) . . . . ? C4 C3 C6 N1 31.8(13) . . . . ? C2 C3 C6 N1 -145.8(11) . . . . ? C4 C3 C6 S1 175.5(9) . . . 2 ? C2 C3 C6 S1 -2.1(12) . . . 2 ? C4 C3 C6 S1 -168.9(9) . . . . ? C2 C3 C6 S1 13.5(12) . . . . ? S1 S1 C6 N1A 119(6) 2 . . . ? C6 S1 C6 N1A 32.7(11) 2 . . . ? S1 S1 C6 N1 70(6) 2 . . . ? C6 S1 C6 N1 -15.8(12) 2 . . . ? S1 S1 C6 C3 -91(6) 2 . . . ? C6 S1 C6 C3 -176.7(8) 2 . . . ? C6 S1 C6 S1 -86(6) 2 . . 2 ? Cu1 O1 C7 O2 -175.7(4) . . . . ? Cu1 O1 C7 C7 1.9(7) . . . 7_565 ? Cu1 O2 C7 O1 -177.5(4) 7_565 . . . ? Cu1 O2 C7 C7 4.9(6) 7_565 . . 7_565 ? Cu1 O4 C8 O3 174.1(4) 7 . . . ? Cu1 O4 C8 O3 16.0(7) 4_545 . . . ? Cu1 O4 C8 C8 -4.4(6) 7 . . 7 ? Cu1 O4 C8 C8 -162.6(4) 4_545 . . 7 ? Cu1 O3 C8 O4 173.5(4) . . . . ? Cu1 O3 C8 C8 -8.0(7) . . . 7 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.907 _refine_diff_density_min -0.949 _refine_diff_density_rms 0.158 # Attachment '2.cif' data_xb2547m _database_code_depnum_ccdc_archive 'CCDC 738468' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 Cu N4 O7 S' _chemical_formula_weight 459.92 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' Cu Cu 0.3201 1.2651 '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' _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 8.9863(17) _cell_length_b 10.0916(18) _cell_length_c 11.218(2) _cell_angle_alpha 90.343(3) _cell_angle_beta 108.875(3) _cell_angle_gamma 109.516(3) _cell_volume 899.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.697 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 470 _exptl_absorpt_coefficient_mu 1.378 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6746 _exptl_absorpt_correction_T_max 0.7073 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4541 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.20 _reflns_number_total 3156 _reflns_number_gt 2433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. During refinement of the structure, 9 restraints were applied including distance restraint (dfix) which have been used in some unreasonable atoms. ; _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^)+(0.0680P)^2^+0.4050P] 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 3156 _refine_ls_number_parameters 256 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.5000 0.5000 0.02028(17) Uani 1 2 d S . . Cu2 Cu 0.5000 1.0000 0.5000 0.02373(18) Uani 1 2 d S . . S1 S 0.18147(13) 0.25142(10) -0.04539(9) 0.0315(2) Uani 1 1 d . . . N1 N 0.4054(4) 0.0303(3) -0.3646(3) 0.0245(6) Uani 1 1 d . . . N2 N 0.0390(3) 0.3963(3) 0.3622(2) 0.0229(6) Uani 1 1 d . . . N3 N 0.1873(4) 0.0731(3) 0.1136(3) 0.0324(7) Uani 1 1 d . . . N4 N 0.2308(4) 0.0252(3) 0.0212(3) 0.0312(7) Uani 1 1 d . . . O1 O 0.4945(3) 0.8101(2) 0.5467(2) 0.0279(6) Uani 1 1 d . . . O2 O 0.2194(3) 0.6971(3) 0.5041(2) 0.0299(6) Uani 1 1 d . . . O3 O 0.3989(4) 0.5152(3) 0.8012(2) 0.0527(8) Uani 1 1 d . . . O4 O 0.1591(3) 0.4413(2) 0.6393(2) 0.0268(5) Uani 1 1 d . . . O5 O 0.2003(4) 0.9085(3) 0.3539(2) 0.0454(7) Uani 1 1 d D . . H5WA H 0.1561 0.8502 0.3954 0.068 Uiso 1 1 d RD . . H5WB H 0.2079 0.8672 0.2938 0.068 Uiso 1 1 d RD . . C1 C 0.2332(4) 0.1074(3) -0.0687(3) 0.0249(8) Uani 1 1 d . . . C2 C 0.1583(4) 0.1911(4) 0.0932(3) 0.0261(8) Uani 1 1 d . . . C3 C 0.1142(4) 0.2628(4) 0.1833(3) 0.0251(8) Uani 1 1 d . . . C4 C 0.3160(5) 0.5075(4) 0.6879(3) 0.0291(8) Uani 1 1 d . . . C5 C 0.0587(5) 0.4567(4) 0.2595(3) 0.0307(8) Uani 1 1 d . . . H5 H 0.0465 0.5443 0.2488 0.037 Uiso 1 1 calc R . . C6 C 0.2859(4) 0.0777(4) -0.1751(3) 0.0247(8) Uani 1 1 d . . . C7 C 0.3695(4) 0.7035(3) 0.5457(3) 0.0238(8) Uani 1 1 d . . . C8 C 0.0909(4) 0.1994(4) 0.2894(3) 0.0260(8) Uani 1 1 d . . . H8 H 0.1014 0.1115 0.3023 0.031 Uiso 1 1 calc R . . C9 C 0.3683(4) -0.0166(4) -0.1659(3) 0.0266(8) Uani 1 1 d . . . H9 H 0.3844 -0.0660 -0.0960 0.032 Uiso 1 1 calc R . . C10 C 0.0964(5) 0.3941(4) 0.1691(3) 0.0300(8) Uani 1 1 d . . . H10 H 0.1099 0.4392 0.0993 0.036 Uiso 1 1 calc R . . C11 C 0.4270(4) -0.0374(4) -0.2616(3) 0.0281(8) Uani 1 1 d . . . H11 H 0.4836 -0.1007 -0.2541 0.034 Uiso 1 1 calc R . . C12 C 0.0526(4) 0.2683(4) 0.3739(3) 0.0250(8) Uani 1 1 d . . . H12 H 0.0349 0.2241 0.4433 0.030 Uiso 1 1 calc R . . C13 C 0.4105(4) 0.5773(4) 0.5993(3) 0.0302(8) Uani 1 1 d . . . H13A H 0.5305 0.6079 0.6457 0.036 Uiso 1 1 calc R . . H13B H 0.3844 0.5068 0.5292 0.036 Uiso 1 1 calc R . . C14 C 0.2597(5) 0.1464(4) -0.2827(3) 0.0312(8) Uani 1 1 d . . . H14 H 0.2022 0.2093 -0.2926 0.037 Uiso 1 1 calc R . . C15 C 0.3204(5) 0.1193(4) -0.3741(3) 0.0316(9) Uani 1 1 d . . . H15 H 0.3018 0.1649 -0.4463 0.038 Uiso 1 1 calc R . . O6 O 0.3808(4) 0.6102(3) 0.0346(3) 0.0601(9) Uani 1 1 d D . . H6WA H 0.3812 0.5839 -0.0359 0.090 Uiso 1 1 d RD . . H6WB H 0.4387 0.5758 0.0895 0.090 Uiso 1 1 d RD . . O7 O 0.2089(4) 0.7521(3) 0.1213(3) 0.0561(8) Uani 1 1 d D . . H7WB H 0.2632 0.7228 0.0876 0.084 Uiso 1 1 d RD . . H7WA H 0.1878 0.8190 0.0859 0.084 Uiso 1 1 d RD . . 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 0.0217(3) 0.0244(3) 0.0212(3) 0.0047(2) 0.0102(2) 0.0135(2) Cu2 0.0257(3) 0.0260(3) 0.0267(3) 0.0048(2) 0.0162(3) 0.0113(3) S1 0.0455(6) 0.0325(5) 0.0332(5) 0.0096(4) 0.0247(4) 0.0237(4) N1 0.0245(16) 0.0322(16) 0.0243(14) 0.0060(12) 0.0128(12) 0.0150(13) N2 0.0242(16) 0.0289(15) 0.0223(14) 0.0038(12) 0.0114(12) 0.0143(12) N3 0.0431(19) 0.0407(18) 0.0274(15) 0.0087(13) 0.0183(14) 0.0262(15) N4 0.0436(19) 0.0393(17) 0.0298(16) 0.0086(13) 0.0226(15) 0.0284(15) O1 0.0254(13) 0.0285(13) 0.0349(13) 0.0069(10) 0.0171(11) 0.0095(11) O2 0.0248(14) 0.0287(13) 0.0387(14) 0.0113(10) 0.0102(11) 0.0132(10) O3 0.0465(19) 0.079(2) 0.0276(15) 0.0154(14) 0.0013(13) 0.0280(16) O4 0.0259(14) 0.0319(13) 0.0303(12) 0.0110(10) 0.0131(11) 0.0161(11) O5 0.0553(19) 0.0461(17) 0.0391(15) 0.0146(13) 0.0188(14) 0.0209(14) C1 0.0227(19) 0.0300(18) 0.0296(18) 0.0023(15) 0.0130(15) 0.0151(15) C2 0.0261(19) 0.0299(19) 0.0279(17) 0.0036(14) 0.0111(15) 0.0152(15) C3 0.0206(18) 0.0304(19) 0.0258(17) -0.0003(14) 0.0096(14) 0.0095(15) C4 0.035(2) 0.0277(19) 0.033(2) 0.0091(15) 0.0130(17) 0.0200(17) C5 0.043(2) 0.0295(19) 0.0335(19) 0.0076(15) 0.0215(18) 0.0216(17) C6 0.0240(19) 0.0277(18) 0.0247(17) 0.0018(14) 0.0110(15) 0.0096(15) C7 0.026(2) 0.0276(18) 0.0203(16) 0.0016(14) 0.0102(15) 0.0110(15) C8 0.031(2) 0.0252(18) 0.0275(17) 0.0048(14) 0.0121(15) 0.0151(15) C9 0.032(2) 0.035(2) 0.0232(17) 0.0057(14) 0.0113(15) 0.0225(16) C10 0.041(2) 0.034(2) 0.0261(17) 0.0105(15) 0.0182(16) 0.0215(18) C11 0.031(2) 0.035(2) 0.0254(17) 0.0024(15) 0.0095(15) 0.0206(16) C12 0.0269(19) 0.0299(19) 0.0229(16) 0.0053(14) 0.0121(15) 0.0126(15) C13 0.0229(19) 0.033(2) 0.039(2) 0.0103(16) 0.0106(16) 0.0152(16) C14 0.036(2) 0.037(2) 0.0356(19) 0.0099(16) 0.0200(17) 0.0244(17) C15 0.036(2) 0.039(2) 0.0307(19) 0.0131(16) 0.0178(17) 0.0215(18) O6 0.069(2) 0.075(2) 0.0509(18) 0.0094(16) 0.0183(17) 0.0465(19) O7 0.063(2) 0.058(2) 0.064(2) 0.0207(16) 0.0297(17) 0.0354(17) _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 O4 1.992(2) . ? Cu1 O4 1.992(2) 2_566 ? Cu1 N2 2.045(3) 2_566 ? Cu1 N2 2.045(3) . ? Cu1 O2 2.273(2) 2_566 ? Cu1 O2 2.273(2) . ? Cu2 O1 1.979(2) . ? Cu2 O1 1.979(2) 2_676 ? Cu2 N1 2.032(3) 1_566 ? Cu2 N1 2.032(3) 2_665 ? Cu2 O5 2.501(3) . ? S1 C1 1.709(3) . ? S1 C2 1.723(3) . ? N1 C11 1.338(4) . ? N1 C15 1.345(4) . ? N1 Cu2 2.032(3) 1_544 ? N2 C5 1.341(4) . ? N2 C12 1.342(4) . ? N3 C2 1.307(4) . ? N3 N4 1.359(4) . ? N4 C1 1.311(4) . ? O1 C7 1.266(4) . ? O2 C7 1.255(4) . ? O3 C4 1.235(4) . ? O4 C4 1.265(4) . ? O5 H5WA 0.8282 . ? O5 H5WB 0.8234 . ? C1 C6 1.482(4) . ? C2 C3 1.465(5) . ? C3 C10 1.390(5) . ? C3 C8 1.397(5) . ? C4 C13 1.537(5) . ? C5 C10 1.378(5) . ? C5 H5 0.9300 . ? C6 C9 1.373(5) . ? C6 C14 1.389(5) . ? C7 C13 1.516(5) . ? C8 C12 1.365(5) . ? C8 H8 0.9300 . ? C9 C11 1.383(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.371(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O6 H6WA 0.8344 . ? O6 H6WB 0.8291 . ? O7 H7WB 0.8263 . ? O7 H7WA 0.8307 . ? 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 O4 Cu1 O4 180.000(1) . 2_566 ? O4 Cu1 N2 87.40(10) . 2_566 ? O4 Cu1 N2 92.60(10) 2_566 2_566 ? O4 Cu1 N2 92.60(10) . . ? O4 Cu1 N2 87.40(10) 2_566 . ? N2 Cu1 N2 180.000(1) 2_566 . ? O4 Cu1 O2 91.48(9) . 2_566 ? O4 Cu1 O2 88.52(9) 2_566 2_566 ? N2 Cu1 O2 90.06(10) 2_566 2_566 ? N2 Cu1 O2 89.94(10) . 2_566 ? O4 Cu1 O2 88.52(9) . . ? O4 Cu1 O2 91.48(9) 2_566 . ? N2 Cu1 O2 89.94(10) 2_566 . ? N2 Cu1 O2 90.06(10) . . ? O2 Cu1 O2 180.00(11) 2_566 . ? O1 Cu2 O1 180.000(1) . 2_676 ? O1 Cu2 N1 91.43(10) . 1_566 ? O1 Cu2 N1 88.57(10) 2_676 1_566 ? O1 Cu2 N1 88.57(10) . 2_665 ? O1 Cu2 N1 91.43(10) 2_676 2_665 ? N1 Cu2 N1 180.000(1) 1_566 2_665 ? O1 Cu2 O5 93.25(9) . . ? O1 Cu2 O5 86.75(9) 2_676 . ? N1 Cu2 O5 85.32(10) 1_566 . ? N1 Cu2 O5 94.68(10) 2_665 . ? C1 S1 C2 87.33(16) . . ? C11 N1 C15 117.5(3) . . ? C11 N1 Cu2 120.8(2) . 1_544 ? C15 N1 Cu2 121.6(2) . 1_544 ? C5 N2 C12 117.7(3) . . ? C5 N2 Cu1 121.0(2) . . ? C12 N2 Cu1 121.1(2) . . ? C2 N3 N4 112.8(3) . . ? C1 N4 N3 112.6(3) . . ? C7 O1 Cu2 128.8(2) . . ? C7 O2 Cu1 122.9(2) . . ? C4 O4 Cu1 125.5(2) . . ? Cu2 O5 H5WA 100.9 . . ? Cu2 O5 H5WB 101.0 . . ? H5WA O5 H5WB 110.2 . . ? N4 C1 C6 121.1(3) . . ? N4 C1 S1 113.9(2) . . ? C6 C1 S1 125.0(3) . . ? N3 C2 C3 121.6(3) . . ? N3 C2 S1 113.4(2) . . ? C3 C2 S1 125.0(3) . . ? C10 C3 C8 117.8(3) . . ? C10 C3 C2 122.7(3) . . ? C8 C3 C2 119.5(3) . . ? O3 C4 O4 124.1(3) . . ? O3 C4 C13 117.9(3) . . ? O4 C4 C13 118.0(3) . . ? N2 C5 C10 122.6(3) . . ? N2 C5 H5 118.7 . . ? C10 C5 H5 118.7 . . ? C9 C6 C14 118.7(3) . . ? C9 C6 C1 119.5(3) . . ? C14 C6 C1 121.9(3) . . ? O2 C7 O1 124.6(3) . . ? O2 C7 C13 119.9(3) . . ? O1 C7 C13 115.5(3) . . ? C12 C8 C3 119.1(3) . . ? C12 C8 H8 120.5 . . ? C3 C8 H8 120.5 . . ? C6 C9 C11 119.4(3) . . ? C6 C9 H9 120.3 . . ? C11 C9 H9 120.3 . . ? C5 C10 C3 119.4(3) . . ? C5 C10 H10 120.3 . . ? C3 C10 H10 120.3 . . ? N1 C11 C9 122.4(3) . . ? N1 C11 H11 118.8 . . ? C9 C11 H11 118.8 . . ? N2 C12 C8 123.4(3) . . ? N2 C12 H12 118.3 . . ? C8 C12 H12 118.3 . . ? C7 C13 C4 114.4(3) . . ? C7 C13 H13A 108.7 . . ? C4 C13 H13A 108.7 . . ? C7 C13 H13B 108.7 . . ? C4 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C6 118.5(3) . . ? C15 C14 H14 120.7 . . ? C6 C14 H14 120.7 . . ? N1 C15 C14 123.4(3) . . ? N1 C15 H15 118.3 . . ? C14 C15 H15 118.3 . . ? H6WA O6 H6WB 108.1 . . ? H7WB O7 H7WA 109.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cu1 N2 C5 -136.8(3) . . . . ? O4 Cu1 N2 C5 43.2(3) 2_566 . . . ? N2 Cu1 N2 C5 -124(100) 2_566 . . . ? O2 Cu1 N2 C5 131.7(3) 2_566 . . . ? O2 Cu1 N2 C5 -48.3(3) . . . . ? O4 Cu1 N2 C12 40.4(3) . . . . ? O4 Cu1 N2 C12 -139.6(3) 2_566 . . . ? N2 Cu1 N2 C12 53(100) 2_566 . . . ? O2 Cu1 N2 C12 -51.1(3) 2_566 . . . ? O2 Cu1 N2 C12 128.9(3) . . . . ? C2 N3 N4 C1 -0.4(4) . . . . ? O1 Cu2 O1 C7 16(100) 2_676 . . . ? N1 Cu2 O1 C7 59.6(3) 1_566 . . . ? N1 Cu2 O1 C7 -120.4(3) 2_665 . . . ? O5 Cu2 O1 C7 -25.8(3) . . . . ? O4 Cu1 O2 C7 23.6(2) . . . . ? O4 Cu1 O2 C7 -156.4(2) 2_566 . . . ? N2 Cu1 O2 C7 111.0(2) 2_566 . . . ? N2 Cu1 O2 C7 -69.0(2) . . . . ? O2 Cu1 O2 C7 -16(100) 2_566 . . . ? O4 Cu1 O4 C4 -135(100) 2_566 . . . ? N2 Cu1 O4 C4 -92.4(3) 2_566 . . . ? N2 Cu1 O4 C4 87.6(3) . . . . ? O2 Cu1 O4 C4 177.6(3) 2_566 . . . ? O2 Cu1 O4 C4 -2.4(3) . . . . ? N3 N4 C1 C6 176.9(3) . . . . ? N3 N4 C1 S1 0.0(4) . . . . ? C2 S1 C1 N4 0.2(3) . . . . ? C2 S1 C1 C6 -176.5(3) . . . . ? N4 N3 C2 C3 -178.3(3) . . . . ? N4 N3 C2 S1 0.6(4) . . . . ? C1 S1 C2 N3 -0.5(3) . . . . ? C1 S1 C2 C3 178.3(3) . . . . ? N3 C2 C3 C10 174.5(3) . . . . ? S1 C2 C3 C10 -4.1(5) . . . . ? N3 C2 C3 C8 -4.5(5) . . . . ? S1 C2 C3 C8 176.8(3) . . . . ? Cu1 O4 C4 O3 144.8(3) . . . . ? Cu1 O4 C4 C13 -37.9(4) . . . . ? C12 N2 C5 C10 -1.8(5) . . . . ? Cu1 N2 C5 C10 175.5(3) . . . . ? N4 C1 C6 C9 -14.6(5) . . . . ? S1 C1 C6 C9 161.9(3) . . . . ? N4 C1 C6 C14 167.6(3) . . . . ? S1 C1 C6 C14 -15.8(5) . . . . ? Cu1 O2 C7 O1 178.3(2) . . . . ? Cu1 O2 C7 C13 -1.6(4) . . . . ? Cu2 O1 C7 O2 5.7(5) . . . . ? Cu2 O1 C7 C13 -174.4(2) . . . . ? C10 C3 C8 C12 -0.1(5) . . . . ? C2 C3 C8 C12 178.9(3) . . . . ? C14 C6 C9 C11 1.9(5) . . . . ? C1 C6 C9 C11 -175.9(3) . . . . ? N2 C5 C10 C3 0.3(6) . . . . ? C8 C3 C10 C5 0.6(5) . . . . ? C2 C3 C10 C5 -178.4(3) . . . . ? C15 N1 C11 C9 -1.2(5) . . . . ? Cu2 N1 C11 C9 178.3(3) 1_544 . . . ? C6 C9 C11 N1 -0.6(5) . . . . ? C5 N2 C12 C8 2.3(5) . . . . ? Cu1 N2 C12 C8 -175.0(3) . . . . ? C3 C8 C12 N2 -1.4(5) . . . . ? O2 C7 C13 C4 -44.1(4) . . . . ? O1 C7 C13 C4 135.9(3) . . . . ? O3 C4 C13 C7 -113.4(4) . . . . ? O4 C4 C13 C7 69.2(4) . . . . ? C9 C6 C14 C15 -1.4(5) . . . . ? C1 C6 C14 C15 176.3(3) . . . . ? C11 N1 C15 C14 1.8(5) . . . . ? Cu2 N1 C15 C14 -177.7(3) 1_544 . . . ? C6 C14 C15 N1 -0.5(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 O7 H7WA N4 0.83 2.16 2.951(4) 159.2 1_565 O7 H7WB O6 0.83 1.99 2.796(4) 164.5 . O6 H6WB O3 0.83 2.06 2.873(4) 168.7 2_666 O6 H6WA O3 0.83 2.02 2.855(4) 175.2 1_554 O5 H5WB O7 0.82 2.26 3.077(4) 175.8 . O5 H5WA O2 0.83 2.09 2.742(3) 135.6 . _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.774 _refine_diff_density_min -0.693 _refine_diff_density_rms 0.091 data_xb2765 _database_code_depnum_ccdc_archive 'CCDC 738469' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 Cu N4 O4 S' _chemical_formula_weight 433.92 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 15.180(8) _cell_length_b 12.571(7) _cell_length_c 8.951(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.759(12) _cell_angle_gamma 90.00 _cell_volume 1699.5(16) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 1.442 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7814 _exptl_absorpt_correction_T_max 0.8460 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(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 8374 _diffrn_reflns_av_R_equivalents 0.1200 _diffrn_reflns_av_sigmaI/netI 0.1965 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.20 _reflns_number_total 3051 _reflns_number_gt 1221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0950P)^2^+0.0932P] 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 3051 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1627 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.2333 _refine_ls_wR_factor_gt 0.1789 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.93158(8) 0.44794(9) 0.43528(13) 0.0380(5) Uani 1 1 d . . . S1 S 0.5578(2) 0.3960(2) -0.1654(3) 0.0541(9) Uani 1 1 d . . . O1 O 0.9931(5) 0.3144(5) 0.4957(7) 0.051(2) Uani 1 1 d . . . O2 O 1.1104(4) 0.4057(5) 0.5991(7) 0.046(2) Uani 1 1 d . . . O3 O 1.1216(5) -0.0473(5) 0.8730(7) 0.0456(18) Uani 1 1 d . . . O4 O 1.0025(5) 0.0401(5) 0.7666(7) 0.0450(18) Uani 1 1 d . . . N1 N 0.8201(6) 0.3860(6) 0.2854(10) 0.049(3) Uani 1 1 d . . . N2 N 0.5976(5) 0.2015(7) -0.1005(8) 0.040(2) Uani 1 1 d . . . N3 N 0.5285(6) 0.1978(7) -0.2162(8) 0.044(2) Uani 1 1 d . . . N4 N 0.2947(7) 0.3440(9) -0.6154(10) 0.068(3) Uani 1 1 d . . . C1 C 1.0684(7) 0.3209(7) 0.5691(11) 0.040(3) Uani 1 1 d . . . C2 C 1.1137(7) 0.2210(7) 0.6269(11) 0.054(3) Uani 1 1 d . . . H2A H 1.0974 0.2081 0.7274 0.064 Uiso 1 1 calc R . . H2B H 1.1771 0.2334 0.6356 0.064 Uiso 1 1 calc R . . C3 C 1.0944(6) 0.1185(7) 0.5334(9) 0.034(2) Uani 1 1 d . . . H3A H 1.0312 0.1123 0.5057 0.041 Uiso 1 1 calc R . . H3B H 1.1234 0.1228 0.4418 0.041 Uiso 1 1 calc R . . C4 C 1.1276(7) 0.0195(7) 0.6229(10) 0.039(3) Uani 1 1 d . . . H4A H 1.1189 -0.0427 0.5589 0.046 Uiso 1 1 calc R . . H4B H 1.1907 0.0267 0.6518 0.046 Uiso 1 1 calc R . . C5 C 1.0810(7) 0.0027(7) 0.7616(11) 0.037(3) Uani 1 1 d . . . C6 C 0.8199(7) 0.2900(8) 0.2159(11) 0.047(3) Uani 1 1 d . . . H6 H 0.8663 0.2435 0.2436 0.057 Uiso 1 1 calc R . . C7 C 0.7545(7) 0.2572(8) 0.1059(10) 0.042(3) Uani 1 1 d . . . H7 H 0.7542 0.1883 0.0679 0.050 Uiso 1 1 calc R . . C8 C 0.6897(6) 0.3296(8) 0.0540(11) 0.039(3) Uani 1 1 d . . . C9 C 0.6883(8) 0.4279(7) 0.1279(12) 0.056(4) Uani 1 1 d . . . H9 H 0.6432 0.4763 0.1013 0.067 Uiso 1 1 calc R . . C10 C 0.7541(7) 0.4523(8) 0.2399(11) 0.047(3) Uani 1 1 d . . . H10 H 0.7524 0.5183 0.2863 0.056 Uiso 1 1 calc R . . C11 C 0.6181(7) 0.3003(8) -0.0615(10) 0.039(3) Uani 1 1 d . . . C12 C 0.5013(7) 0.2924(8) -0.2617(11) 0.043(3) Uani 1 1 d . . . C13 C 0.3161(8) 0.2468(11) -0.5611(13) 0.065(4) Uani 1 1 d . . . H13 H 0.2845 0.1890 -0.6033 0.078 Uiso 1 1 calc R . . C14 C 0.3821(7) 0.2271(9) -0.4468(11) 0.047(3) Uani 1 1 d . . . H14 H 0.3949 0.1576 -0.4163 0.057 Uiso 1 1 calc R . . C15 C 0.4288(7) 0.3102(9) -0.3782(11) 0.044(3) Uani 1 1 d . . . C16 C 0.4073(7) 0.4137(9) -0.4287(11) 0.050(3) Uani 1 1 d . . . H16 H 0.4374 0.4729 -0.3872 0.059 Uiso 1 1 calc R . . C17 C 0.3384(8) 0.4238(9) -0.5449(10) 0.058(4) Uani 1 1 d . . . H17 H 0.3219 0.4924 -0.5750 0.070 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 0.0527(9) 0.0147(6) 0.0441(7) -0.0016(6) -0.0081(6) -0.0006(7) S1 0.069(2) 0.0299(16) 0.0581(17) -0.0012(14) -0.0195(16) -0.0040(15) O1 0.075(6) 0.010(4) 0.062(5) -0.004(3) -0.031(4) 0.001(4) O2 0.064(5) 0.015(4) 0.055(4) -0.006(3) -0.015(4) 0.002(4) O3 0.058(5) 0.027(4) 0.051(4) 0.001(4) 0.000(4) 0.016(4) O4 0.048(5) 0.033(4) 0.054(4) 0.007(4) 0.004(4) 0.004(4) N1 0.053(6) 0.017(5) 0.070(6) -0.004(4) -0.027(5) 0.008(4) N2 0.060(6) 0.029(5) 0.032(4) -0.005(4) 0.003(4) 0.001(4) N3 0.053(6) 0.045(6) 0.032(4) -0.013(4) -0.001(4) 0.004(5) N4 0.075(8) 0.068(8) 0.054(6) -0.017(6) -0.026(6) 0.014(6) C1 0.040(7) 0.021(6) 0.056(6) 0.003(5) -0.015(6) 0.006(5) C2 0.080(9) 0.006(5) 0.066(7) -0.004(5) -0.036(7) 0.007(5) C3 0.045(7) 0.025(6) 0.034(5) 0.004(4) 0.011(5) -0.004(5) C4 0.058(7) 0.017(5) 0.041(5) 0.005(5) -0.001(5) -0.001(5) C5 0.048(8) 0.016(5) 0.045(6) -0.017(5) 0.002(6) 0.000(5) C6 0.042(7) 0.036(7) 0.063(7) 0.006(6) 0.001(6) 0.008(6) C7 0.056(8) 0.034(7) 0.034(6) 0.004(5) 0.005(6) -0.004(6) C8 0.025(6) 0.038(6) 0.052(6) 0.006(5) -0.002(5) 0.002(5) C9 0.071(9) 0.013(6) 0.075(8) -0.006(5) -0.039(7) 0.007(5) C10 0.050(7) 0.024(6) 0.065(7) -0.002(6) -0.008(6) -0.003(6) C11 0.047(7) 0.033(6) 0.036(5) 0.003(5) 0.001(5) 0.003(5) C12 0.039(7) 0.032(6) 0.055(7) -0.008(6) -0.003(5) -0.003(5) C13 0.055(8) 0.075(10) 0.063(8) -0.007(7) -0.009(7) -0.008(7) C14 0.048(8) 0.045(7) 0.050(6) -0.003(6) 0.011(6) -0.004(6) C15 0.032(7) 0.048(8) 0.051(6) -0.011(6) 0.005(5) -0.003(6) C16 0.060(8) 0.047(8) 0.040(6) -0.005(5) -0.005(6) 0.000(6) C17 0.087(10) 0.064(9) 0.025(5) -0.001(5) 0.010(6) 0.021(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.946(7) 4_565 ? Cu1 O2 1.962(6) 3_766 ? Cu1 O3 1.969(7) 2_756 ? Cu1 O1 1.970(6) . ? Cu1 N1 2.194(8) . ? Cu1 Cu1 2.624(2) 3_766 ? S1 C11 1.725(10) . ? S1 C12 1.739(10) . ? O1 C1 1.262(11) . ? O2 C1 1.256(11) . ? O2 Cu1 1.962(6) 3_766 ? O3 C5 1.284(11) . ? O3 Cu1 1.969(7) 2_746 ? O4 C5 1.286(11) . ? O4 Cu1 1.946(7) 4_566 ? N1 C10 1.335(12) . ? N1 C6 1.358(12) . ? N2 C11 1.318(12) . ? N2 N3 1.399(10) . ? N3 C12 1.309(12) . ? N4 C17 1.327(13) . ? N4 C13 1.343(14) . ? C1 C2 1.499(12) . ? C2 C3 1.549(12) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.538(12) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.504(13) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 C7 1.389(12) . ? C6 H6 0.9300 . ? C7 C8 1.385(13) . ? C7 H7 0.9300 . ? C8 C9 1.403(13) . ? C8 C11 1.470(13) . ? C9 C10 1.377(13) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C12 C15 1.456(13) . ? C13 C14 1.380(14) . ? C13 H13 0.9300 . ? C14 C15 1.373(14) . ? C14 H14 0.9300 . ? C15 C16 1.405(14) . ? C16 C17 1.405(13) . ? 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 O4 Cu1 O2 90.1(3) 4_565 3_766 ? O4 Cu1 O3 168.8(3) 4_565 2_756 ? O2 Cu1 O3 87.3(3) 3_766 2_756 ? O4 Cu1 O1 89.7(3) 4_565 . ? O2 Cu1 O1 168.5(3) 3_766 . ? O3 Cu1 O1 90.6(3) 2_756 . ? O4 Cu1 N1 90.3(3) 4_565 . ? O2 Cu1 N1 91.1(3) 3_766 . ? O3 Cu1 N1 100.7(3) 2_756 . ? O1 Cu1 N1 100.4(3) . . ? O4 Cu1 Cu1 80.2(2) 4_565 3_766 ? O2 Cu1 Cu1 80.30(19) 3_766 3_766 ? O3 Cu1 Cu1 88.6(2) 2_756 3_766 ? O1 Cu1 Cu1 88.4(2) . 3_766 ? N1 Cu1 Cu1 167.1(2) . 3_766 ? C11 S1 C12 87.3(5) . . ? C1 O1 Cu1 117.8(6) . . ? C1 O2 Cu1 127.7(6) . 3_766 ? C5 O3 Cu1 119.0(7) . 2_746 ? C5 O4 Cu1 129.9(6) . 4_566 ? C10 N1 C6 116.6(9) . . ? C10 N1 Cu1 118.3(7) . . ? C6 N1 Cu1 124.2(7) . . ? C11 N2 N3 111.5(8) . . ? C12 N3 N2 112.9(8) . . ? C17 N4 C13 115.2(10) . . ? O2 C1 O1 125.5(9) . . ? O2 C1 C2 115.5(9) . . ? O1 C1 C2 119.0(9) . . ? C1 C2 C3 117.1(8) . . ? C1 C2 H2A 108.0 . . ? C3 C2 H2A 108.0 . . ? C1 C2 H2B 108.0 . . ? C3 C2 H2B 108.0 . . ? H2A C2 H2B 107.3 . . ? C4 C3 C2 111.0(7) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 112.7(8) . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? O3 C5 O4 121.8(9) . . ? O3 C5 C4 118.7(10) . . ? O4 C5 C4 119.5(9) . . ? N1 C6 C7 123.8(9) . . ? N1 C6 H6 118.1 . . ? C7 C6 H6 118.1 . . ? C8 C7 C6 118.4(10) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C7 C8 C9 117.6(9) . . ? C7 C8 C11 121.4(9) . . ? C9 C8 C11 120.5(9) . . ? C10 C9 C8 119.7(9) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? N1 C10 C9 123.4(10) . . ? N1 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? N2 C11 C8 124.0(9) . . ? N2 C11 S1 114.6(7) . . ? C8 C11 S1 121.3(8) . . ? N3 C12 C15 123.7(9) . . ? N3 C12 S1 113.6(8) . . ? C15 C12 S1 122.7(8) . . ? N4 C13 C14 124.2(11) . . ? N4 C13 H13 117.9 . . ? C14 C13 H13 117.9 . . ? C15 C14 C13 119.9(11) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 117.9(10) . . ? C14 C15 C12 121.5(11) . . ? C16 C15 C12 120.5(9) . . ? C17 C16 C15 117.0(10) . . ? C17 C16 H16 121.5 . . ? C15 C16 H16 121.5 . . ? N4 C17 C16 125.7(11) . . ? N4 C17 H17 117.2 . . ? C16 C17 H17 117.2 . . ? 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 O4 Cu1 O1 C1 80.8(8) 4_565 . . . ? O2 Cu1 O1 C1 -8(2) 3_766 . . . ? O3 Cu1 O1 C1 -87.9(8) 2_756 . . . ? N1 Cu1 O1 C1 171.1(8) . . . . ? Cu1 Cu1 O1 C1 0.7(8) 3_766 . . . ? O4 Cu1 N1 C10 -101.1(8) 4_565 . . . ? O2 Cu1 N1 C10 -11.0(8) 3_766 . . . ? O3 Cu1 N1 C10 76.5(8) 2_756 . . . ? O1 Cu1 N1 C10 169.1(8) . . . . ? Cu1 Cu1 N1 C10 -58.7(16) 3_766 . . . ? O4 Cu1 N1 C6 67.7(9) 4_565 . . . ? O2 Cu1 N1 C6 157.8(9) 3_766 . . . ? O3 Cu1 N1 C6 -114.7(9) 2_756 . . . ? O1 Cu1 N1 C6 -22.1(9) . . . . ? Cu1 Cu1 N1 C6 110.0(11) 3_766 . . . ? C11 N2 N3 C12 1.4(12) . . . . ? Cu1 O2 C1 O1 8.0(17) 3_766 . . . ? Cu1 O2 C1 C2 -172.2(7) 3_766 . . . ? Cu1 O1 C1 O2 -4.9(15) . . . . ? Cu1 O1 C1 C2 175.3(7) . . . . ? O2 C1 C2 C3 -149.1(10) . . . . ? O1 C1 C2 C3 30.8(16) . . . . ? C1 C2 C3 C4 -167.1(9) . . . . ? C2 C3 C4 C5 63.2(11) . . . . ? Cu1 O3 C5 O4 -7.5(12) 2_746 . . . ? Cu1 O3 C5 C4 171.4(6) 2_746 . . . ? Cu1 O4 C5 O3 9.4(13) 4_566 . . . ? Cu1 O4 C5 C4 -169.5(6) 4_566 . . . ? C3 C4 C5 O3 -153.3(8) . . . . ? C3 C4 C5 O4 25.5(12) . . . . ? C10 N1 C6 C7 -2.0(16) . . . . ? Cu1 N1 C6 C7 -171.0(7) . . . . ? N1 C6 C7 C8 5.9(16) . . . . ? C6 C7 C8 C9 -7.1(15) . . . . ? C6 C7 C8 C11 -179.6(9) . . . . ? C7 C8 C9 C10 4.8(16) . . . . ? C11 C8 C9 C10 177.5(10) . . . . ? C6 N1 C10 C9 -0.5(17) . . . . ? Cu1 N1 C10 C9 169.1(9) . . . . ? C8 C9 C10 N1 -1.0(18) . . . . ? N3 N2 C11 C8 -178.2(9) . . . . ? N3 N2 C11 S1 -1.8(11) . . . . ? C7 C8 C11 N2 15.6(16) . . . . ? C9 C8 C11 N2 -156.8(10) . . . . ? C7 C8 C11 S1 -160.6(8) . . . . ? C9 C8 C11 S1 27.1(14) . . . . ? C12 S1 C11 N2 1.4(9) . . . . ? C12 S1 C11 C8 177.9(9) . . . . ? N2 N3 C12 C15 -178.4(9) . . . . ? N2 N3 C12 S1 -0.4(11) . . . . ? C11 S1 C12 N3 -0.5(9) . . . . ? C11 S1 C12 C15 177.5(9) . . . . ? C17 N4 C13 C14 -3.9(19) . . . . ? N4 C13 C14 C15 1.9(18) . . . . ? C13 C14 C15 C16 -0.3(16) . . . . ? C13 C14 C15 C12 -177.3(10) . . . . ? N3 C12 C15 C14 1.5(16) . . . . ? S1 C12 C15 C14 -176.4(8) . . . . ? N3 C12 C15 C16 -175.5(10) . . . . ? S1 C12 C15 C16 6.7(15) . . . . ? C14 C15 C16 C17 0.9(15) . . . . ? C12 C15 C16 C17 177.9(9) . . . . ? C13 N4 C17 C16 4.7(18) . . . . ? C15 C16 C17 N4 -3.3(17) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.055 _refine_diff_density_min -1.649 _refine_diff_density_rms 0.376 # Attachment '4.cif' data_xb2771m _database_code_depnum_ccdc_archive 'CCDC 738470' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Cu N4 O4 S' _chemical_formula_sum 'C18 H16 Cu N4 O4 S' _chemical_formula_weight 447.95 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 '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 9.124(2) _cell_length_b 9.649(2) _cell_length_c 11.613(3) _cell_angle_alpha 91.850(4) _cell_angle_beta 104.821(4) _cell_angle_gamma 112.236(4) _cell_volume 905.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 458 _exptl_absorpt_coefficient_mu 1.356 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8225 _exptl_absorpt_correction_T_max 0.9353 _exptl_absorpt_process_details SADABS _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 'Bruker APEX SMART II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4918 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0921 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3463 _reflns_number_gt 1970 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0863P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3463 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1385 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 0.841 _refine_ls_restrained_S_all 0.841 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.38904(7) 0.58001(6) -0.10783(5) 0.0368(2) Uani 1 1 d . . . S1 S 0.46170(15) 1.12721(13) 0.39295(11) 0.0365(3) Uani 1 1 d . . . O1 O 0.1496(4) 0.5264(4) -0.1868(3) 0.0427(8) Uani 1 1 d . . . O2 O 0.2605(5) 0.7262(5) -0.2691(4) 0.0747(13) Uani 1 1 d . . . O3 O 0.6262(4) 0.6207(3) -0.0270(3) 0.0380(8) Uani 1 1 d . . . O4 O 0.6572(4) 0.8032(4) -0.1380(3) 0.0532(9) Uani 1 1 d . . . N1 N 0.3800(4) 0.7089(4) 0.0281(3) 0.0312(9) Uani 1 1 d . . . N2 N 0.3802(4) 1.4374(4) 0.7561(3) 0.0330(9) Uani 1 1 d . . . N3 N 0.1855(5) 0.9024(5) 0.3416(4) 0.0550(12) Uani 1 1 d . . . N4 N 0.1843(5) 0.9937(5) 0.4321(4) 0.0593(13) Uani 1 1 d . . . C1 C 0.2495(6) 1.3054(5) 0.7200(5) 0.0466(13) Uani 1 1 d . . . H1 H 0.1684 1.2841 0.7595 0.056 Uiso 1 1 calc R . . C2 C 0.2266(6) 1.1991(5) 0.6286(4) 0.0437(13) Uani 1 1 d . . . H2 H 0.1332 1.1086 0.6079 0.052 Uiso 1 1 calc R . . C3 C 0.3449(5) 1.2284(5) 0.5674(4) 0.0340(11) Uani 1 1 d . . . C4 C 0.4806(6) 1.3644(5) 0.6050(4) 0.0400(12) Uani 1 1 d . . . H4 H 0.5639 1.3888 0.5674 0.048 Uiso 1 1 calc R . . C5 C 0.4930(5) 1.4630(5) 0.6969(4) 0.0363(11) Uani 1 1 d . . . H5 H 0.5858 1.5538 0.7199 0.044 Uiso 1 1 calc R . . C6 C 0.3199(6) 1.1137(5) 0.4691(4) 0.0354(11) Uani 1 1 d . . . C7 C 0.3209(5) 0.9566(5) 0.3108(4) 0.0340(11) Uani 1 1 d . . . C8 C 0.2279(5) 0.7286(5) 0.1627(4) 0.0336(11) Uani 1 1 d . . . H8 H 0.1355 0.6844 0.1899 0.040 Uiso 1 1 calc R . . C9 C 0.2492(5) 0.6523(5) 0.0706(4) 0.0353(11) Uani 1 1 d . . . H9 H 0.1687 0.5566 0.0361 0.042 Uiso 1 1 calc R . . C10 C 0.4936(6) 0.8480(5) 0.0778(4) 0.0376(11) Uani 1 1 d . . . H10 H 0.5847 0.8894 0.0487 0.045 Uiso 1 1 calc R . . C11 C 0.4813(6) 0.9314(5) 0.1694(4) 0.0398(12) Uani 1 1 d . . . H11 H 0.5634 1.0272 0.2014 0.048 Uiso 1 1 calc R . . C12 C 0.3467(5) 0.8740(5) 0.2153(4) 0.0324(11) Uani 1 1 d . . . C13 C 0.7171(6) 0.7341(5) -0.0676(4) 0.0352(11) Uani 1 1 d . . . C14 C 0.9005(5) 0.7790(5) -0.0246(5) 0.0502(14) Uani 1 1 d . . . H14B H 0.9278 0.7088 -0.0677 0.060 Uiso 1 1 calc R . . H14A H 0.9310 0.7688 0.0601 0.060 Uiso 1 1 calc R . . C15 C 1.0039(6) 0.9388(5) -0.0403(5) 0.0504(14) Uani 1 1 d . . . H15A H 1.1182 0.9511 -0.0236 0.060 Uiso 1 1 calc R . . H15B H 0.9666 0.9523 -0.1235 0.060 Uiso 1 1 calc R . . C16 C 0.1401(6) 0.6163(6) -0.2637(5) 0.0449(13) Uani 1 1 d . . . C17 C -0.0255(7) 0.5821(7) -0.3543(5) 0.0641(17) Uani 1 1 d . . . H17C H -0.1069 0.4917 -0.3380 0.077 Uiso 0.53 1 calc PR A 1 H17D H -0.0583 0.6648 -0.3424 0.077 Uiso 0.53 1 calc PR A 1 H17A H -0.1076 0.4944 -0.3355 0.077 Uiso 0.47 1 d PR A 2 H17B H -0.0563 0.6669 -0.3457 0.077 Uiso 0.47 1 d PR A 2 C18 C -0.030(3) 0.559(2) -0.4819(16) 0.063(5) Uani 0.47 1 d P . 1 H18A H 0.0374 0.6555 -0.5014 0.076 Uiso 0.47 1 calc PR . 1 H18B H -0.1426 0.5318 -0.5312 0.076 Uiso 0.47 1 calc PR . 1 C18A C -0.0606(18) 0.4765(18) -0.4631(13) 0.050(4) Uani 0.53 1 d P . 2 H18C H -0.1692 0.4601 -0.5151 0.060 Uiso 0.53 1 calc PR . 2 H18D H -0.0663 0.3800 -0.4381 0.060 Uiso 0.53 1 calc PR . 2 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 0.0284(3) 0.0396(4) 0.0371(4) -0.0159(3) 0.0088(3) 0.0098(3) S1 0.0374(7) 0.0341(7) 0.0341(7) -0.0105(5) 0.0156(5) 0.0081(5) O1 0.0334(19) 0.044(2) 0.045(2) -0.0079(17) 0.0123(16) 0.0101(16) O2 0.044(2) 0.073(3) 0.074(3) 0.008(2) 0.008(2) -0.006(2) O3 0.0342(18) 0.0291(17) 0.047(2) -0.0042(15) 0.0168(16) 0.0069(15) O4 0.041(2) 0.055(2) 0.054(3) 0.0065(19) 0.0029(18) 0.0169(18) N1 0.030(2) 0.033(2) 0.029(2) -0.0080(16) 0.0076(17) 0.0123(17) N2 0.024(2) 0.034(2) 0.033(2) -0.0112(17) 0.0074(17) 0.0050(17) N3 0.041(3) 0.044(3) 0.065(3) -0.030(2) 0.026(2) -0.004(2) N4 0.044(3) 0.053(3) 0.069(3) -0.034(2) 0.031(2) 0.000(2) C1 0.040(3) 0.051(3) 0.048(3) -0.012(3) 0.024(3) 0.012(3) C2 0.037(3) 0.040(3) 0.044(3) -0.018(2) 0.017(2) 0.003(2) C3 0.030(3) 0.034(3) 0.033(3) -0.009(2) 0.008(2) 0.009(2) C4 0.036(3) 0.045(3) 0.041(3) -0.007(2) 0.021(2) 0.013(2) C5 0.029(2) 0.034(3) 0.039(3) -0.010(2) 0.011(2) 0.006(2) C6 0.041(3) 0.037(3) 0.030(3) -0.009(2) 0.016(2) 0.015(2) C7 0.033(3) 0.029(2) 0.036(3) -0.009(2) 0.008(2) 0.010(2) C8 0.033(3) 0.033(3) 0.035(3) -0.007(2) 0.013(2) 0.012(2) C9 0.032(3) 0.029(3) 0.042(3) -0.003(2) 0.012(2) 0.009(2) C10 0.031(3) 0.034(3) 0.043(3) -0.010(2) 0.016(2) 0.005(2) C11 0.038(3) 0.030(3) 0.043(3) -0.013(2) 0.010(2) 0.007(2) C12 0.034(3) 0.034(3) 0.029(3) -0.003(2) 0.007(2) 0.016(2) C13 0.033(3) 0.027(3) 0.041(3) -0.011(2) 0.013(2) 0.007(2) C14 0.028(3) 0.036(3) 0.081(4) 0.001(3) 0.017(3) 0.007(2) C15 0.029(3) 0.045(3) 0.072(4) 0.001(3) 0.021(3) 0.005(2) C16 0.034(3) 0.053(3) 0.039(3) -0.008(3) 0.009(2) 0.010(3) C17 0.041(3) 0.094(5) 0.051(4) -0.010(3) 0.005(3) 0.027(3) C18 0.053(11) 0.094(15) 0.038(9) 0.024(11) -0.005(7) 0.035(12) C18A 0.035(7) 0.073(10) 0.036(8) 0.003(7) 0.007(6) 0.019(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 Cu1 O1 1.992(3) . ? Cu1 O3 2.003(3) . ? Cu1 N1 2.015(3) . ? Cu1 N2 2.027(4) 1_544 ? S1 C6 1.714(4) . ? S1 C7 1.715(4) . ? O1 C16 1.275(6) . ? O2 C16 1.222(6) . ? O3 C13 1.286(5) . ? O4 C13 1.222(5) . ? N1 C9 1.340(5) . ? N1 C10 1.341(5) . ? N2 C5 1.331(5) . ? N2 C1 1.334(6) . ? N2 Cu1 2.027(4) 1_566 ? N3 C7 1.295(6) . ? N3 N4 1.354(5) . ? N4 C6 1.291(6) . ? C1 C2 1.370(6) . ? C1 H1 0.9300 . ? C2 C3 1.388(6) . ? C2 H2 0.9300 . ? C3 C4 1.379(6) . ? C3 C6 1.474(6) . ? C4 C5 1.360(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C12 1.463(6) . ? C8 C9 1.374(6) . ? C8 C12 1.404(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.367(6) . ? C10 H10 0.9300 . ? C11 C12 1.392(6) . ? C11 H11 0.9300 . ? C13 C14 1.499(6) . ? C14 C15 1.519(6) . ? C14 H14B 0.9700 . ? C14 H14A 0.9700 . ? C15 C15 1.517(9) 2_775 ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.512(7) . ? C17 C18 1.48(2) . ? C17 C18A 1.483(16) . ? C17 H17C 0.9700 . ? C17 H17D 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C18 1.53(4) 2_564 ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18A C18A 1.51(3) 2_564 ? C18A H18C 0.9700 . ? C18A H18D 0.9700 . ? 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 O3 176.50(13) . . ? O1 Cu1 N1 89.64(14) . . ? O3 Cu1 N1 91.79(13) . . ? O1 Cu1 N2 86.93(13) . 1_544 ? O3 Cu1 N2 91.46(13) . 1_544 ? N1 Cu1 N2 175.30(15) . 1_544 ? C6 S1 C7 86.4(2) . . ? C16 O1 Cu1 107.2(3) . . ? C13 O3 Cu1 108.0(3) . . ? C9 N1 C10 117.5(4) . . ? C9 N1 Cu1 117.4(3) . . ? C10 N1 Cu1 125.0(3) . . ? C5 N2 C1 115.7(4) . . ? C5 N2 Cu1 126.1(3) . 1_566 ? C1 N2 Cu1 118.2(3) . 1_566 ? C7 N3 N4 112.8(4) . . ? C6 N4 N3 112.4(4) . . ? N2 C1 C2 124.4(4) . . ? N2 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C1 C2 C3 119.0(4) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 116.7(4) . . ? C4 C3 C6 124.5(4) . . ? C2 C3 C6 118.8(4) . . ? C5 C4 C3 120.2(4) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? N2 C5 C4 124.0(4) . . ? N2 C5 H5 118.0 . . ? C4 C5 H5 118.0 . . ? N4 C6 C3 121.4(4) . . ? N4 C6 S1 114.3(3) . . ? C3 C6 S1 124.2(3) . . ? N3 C7 C12 121.1(4) . . ? N3 C7 S1 114.0(3) . . ? C12 C7 S1 124.9(3) . . ? C9 C8 C12 119.4(4) . . ? C9 C8 H8 120.3 . . ? C12 C8 H8 120.3 . . ? N1 C9 C8 123.3(4) . . ? N1 C9 H9 118.4 . . ? C8 C9 H9 118.4 . . ? N1 C10 C11 122.8(4) . . ? N1 C10 H10 118.6 . . ? C11 C10 H10 118.6 . . ? C10 C11 C12 120.4(4) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C8 116.5(4) . . ? C11 C12 C7 124.2(4) . . ? C8 C12 C7 119.2(4) . . ? O4 C13 O3 121.7(4) . . ? O4 C13 C14 121.1(4) . . ? O3 C13 C14 117.2(4) . . ? C13 C14 C15 114.9(4) . . ? C13 C14 H14B 108.5 . . ? C15 C14 H14B 108.5 . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? H14B C14 H14A 107.5 . . ? C15 C15 C14 113.9(5) 2_775 . ? C15 C15 H15A 108.8 2_775 . ? C14 C15 H15A 108.8 . . ? C15 C15 H15B 108.8 2_775 . ? C14 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? O2 C16 O1 122.5(5) . . ? O2 C16 C17 118.9(5) . . ? O1 C16 C17 118.6(5) . . ? C18 C17 C18A 31.3(6) . . ? C18 C17 C16 115.2(9) . . ? C18A C17 C16 113.8(8) . . ? C18 C17 H17C 108.5 . . ? C18A C17 H17C 80.3 . . ? C16 C17 H17C 108.5 . . ? C18 C17 H17D 108.5 . . ? C18A C17 H17D 131.8 . . ? C16 C17 H17D 108.5 . . ? H17C C17 H17D 107.5 . . ? C18 C17 H17A 110.6 . . ? C18A C17 H17A 82.6 . . ? C16 C17 H17A 108.3 . . ? H17C C17 H17A 2.5 . . ? H17D C17 H17A 105.3 . . ? C18 C17 H17B 105.9 . . ? C18A C17 H17B 130.0 . . ? C16 C17 H17B 108.9 . . ? H17C C17 H17B 109.8 . . ? H17D C17 H17B 2.8 . . ? H17A C17 H17B 107.7 . . ? C17 C18 C18 117.0(16) . 2_564 ? C17 C18 H18A 108.1 . . ? C18 C18 H18A 108.1 2_564 . ? C17 C18 H18B 108.1 . . ? C18 C18 H18B 108.1 2_564 . ? H18A C18 H18B 107.3 . . ? C17 C18A C18A 117.2(15) . 2_564 ? C17 C18A H18C 108.0 . . ? C18A C18A H18C 108.0 2_564 . ? C17 C18A H18D 108.0 . . ? C18A C18A H18D 108.0 2_564 . ? H18C C18A H18D 107.3 . . ? 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 O1 C16 95.8(3) . . . . ? N2 Cu1 O1 C16 -87.4(3) 1_544 . . . ? N1 Cu1 O3 C13 -93.8(3) . . . . ? N2 Cu1 O3 C13 89.6(3) 1_544 . . . ? O1 Cu1 N1 C9 43.0(3) . . . . ? O3 Cu1 N1 C9 -133.8(3) . . . . ? O3 Cu1 N1 C10 47.3(4) . . . . ? C7 N3 N4 C6 -1.1(7) . . . . ? C5 N2 C1 C2 0.0(7) . . . . ? Cu1 N2 C1 C2 179.4(4) 1_566 . . . ? N2 C1 C2 C3 -0.5(8) . . . . ? C1 C2 C3 C4 0.8(7) . . . . ? C1 C2 C3 C6 180.0(4) . . . . ? C2 C3 C4 C5 -0.7(7) . . . . ? C6 C3 C4 C5 -179.8(5) . . . . ? C1 N2 C5 C4 0.1(7) . . . . ? Cu1 N2 C5 C4 -179.1(4) 1_566 . . . ? C3 C4 C5 N2 0.2(8) . . . . ? N3 N4 C6 C3 -179.9(4) . . . . ? N3 N4 C6 S1 1.2(6) . . . . ? C4 C3 C6 N4 -174.6(5) . . . . ? C2 C3 C6 N4 6.3(7) . . . . ? C4 C3 C6 S1 4.1(7) . . . . ? C2 C3 C6 S1 -174.9(4) . . . . ? C7 S1 C6 N4 -0.8(4) . . . . ? C7 S1 C6 C3 -179.7(4) . . . . ? N4 N3 C7 C12 179.4(4) . . . . ? N4 N3 C7 S1 0.5(6) . . . . ? C6 S1 C7 N3 0.2(4) . . . . ? C6 S1 C7 C12 -178.8(4) . . . . ? C10 N1 C9 C8 -0.9(7) . . . . ? Cu1 N1 C9 C8 -179.8(3) . . . . ? C12 C8 C9 N1 0.7(7) . . . . ? C9 N1 C10 C11 0.7(7) . . . . ? Cu1 N1 C10 C11 179.5(3) . . . . ? N1 C10 C11 C12 -0.3(7) . . . . ? C10 C11 C12 C8 0.1(7) . . . . ? C10 C11 C12 C7 -178.3(4) . . . . ? C9 C8 C12 C11 -0.3(6) . . . . ? C9 C8 C12 C7 178.1(4) . . . . ? N3 C7 C12 C11 173.4(5) . . . . ? S1 C7 C12 C11 -7.7(7) . . . . ? N3 C7 C12 C8 -4.8(7) . . . . ? S1 C7 C12 C8 174.0(4) . . . . ? Cu1 O3 C13 O4 3.8(5) . . . . ? Cu1 O3 C13 C14 -176.4(3) . . . . ? O4 C13 C14 C15 19.0(7) . . . . ? O3 C13 C14 C15 -160.7(4) . . . . ? C13 C14 C15 C15 68.5(7) . . . 2_775 ? Cu1 O1 C16 O2 -9.7(6) . . . . ? Cu1 O1 C16 C17 168.0(4) . . . . ? O2 C16 C17 C18 57.8(11) . . . . ? O1 C16 C17 C18 -120.0(10) . . . . ? O2 C16 C17 C18A 92.3(9) . . . . ? O1 C16 C17 C18A -85.5(8) . . . . ? C18A C17 C18 C18 -40.6(14) . . . 2_564 ? C16 C17 C18 C18 54(3) . . . 2_564 ? C18 C17 C18A C18A 41.2(15) . . . 2_564 ? C16 C17 C18A C18A -59(2) . . . 2_564 ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.644 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.140 # Attachment '5.cif' data_xb2186 _database_code_depnum_ccdc_archive 'CCDC 738471' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H26 Cu2 N8 O11 S2' _chemical_formula_sum 'C32 H26 Cu2 N8 O11 S2' _chemical_formula_weight 889.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pcca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 15.945(4) _cell_length_b 14.811(4) _cell_length_c 15.159(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3580.0(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 1.377 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7143 _exptl_absorpt_correction_T_max 0.8359 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17173 _diffrn_reflns_av_R_equivalents 0.0965 _diffrn_reflns_av_sigmaI/netI 0.0848 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.19 _reflns_number_total 3222 _reflns_number_gt 1476 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0310P)^2^+0.0528P] 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 3222 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.43780(3) 1.17295(4) 0.37258(4) 0.03209(19) Uani 1 1 d . . . S1 S 0.47151(8) 0.67317(9) 0.37732(10) 0.0436(4) Uani 1 1 d . . . N1 N 0.4360(2) 1.0374(2) 0.3596(2) 0.0306(10) Uani 1 1 d . . . N2 N 0.3498(3) 0.7188(3) 0.2781(3) 0.0452(13) Uani 1 1 d . . . N3 N 0.3506(3) 0.6267(3) 0.2782(3) 0.0455(13) Uani 1 1 d . . . N4 N 0.4344(2) 0.3084(2) 0.3605(2) 0.0310(10) Uani 1 1 d . . . O1 O 0.55484(17) 1.1738(2) 0.4107(2) 0.0347(8) Uani 1 1 d . . . O2 O 0.60742(19) 1.1734(2) 0.2756(2) 0.0493(10) Uani 1 1 d . . . O3 O 0.81856(18) 1.1671(2) 0.5911(2) 0.0385(9) Uani 1 1 d . . . O4 O 0.8633(2) 1.2242(3) 0.4643(2) 0.0601(12) Uani 1 1 d . . . C1 C 0.4961(3) 0.9809(3) 0.3842(3) 0.0380(13) Uani 1 1 d . . . H1 H 0.5445 1.0052 0.4087 0.046 Uiso 1 1 calc R . . C2 C 0.4913(3) 0.8891(3) 0.3758(3) 0.0364(12) Uani 1 1 d . . . H2 H 0.5347 0.8525 0.3960 0.044 Uiso 1 1 calc R . . C3 C 0.4208(3) 0.8513(3) 0.3366(3) 0.0333(13) Uani 1 1 d . . . C4 C 0.3583(3) 0.9094(3) 0.3093(3) 0.0391(14) Uani 1 1 d . . . H4 H 0.3099 0.8873 0.2829 0.047 Uiso 1 1 calc R . . C5 C 0.3689(3) 0.9998(3) 0.3216(3) 0.0434(15) Uani 1 1 d . . . H5 H 0.3265 1.0381 0.3022 0.052 Uiso 1 1 calc R . . C6 C 0.4097(3) 0.7522(3) 0.3264(3) 0.0356(14) Uani 1 1 d . . . C7 C 0.4095(3) 0.5929(3) 0.3284(3) 0.0381(14) Uani 1 1 d . . . C8 C 0.4202(3) 0.4948(3) 0.3411(3) 0.0400(15) Uani 1 1 d . . . C9 C 0.4896(3) 0.4568(3) 0.3794(3) 0.0448(14) Uani 1 1 d . . . H9 H 0.5329 0.4931 0.4000 0.054 Uiso 1 1 calc R . . C10 C 0.4945(3) 0.3650(3) 0.3872(3) 0.0391(14) Uani 1 1 d . . . H10 H 0.5425 0.3405 0.4125 0.047 Uiso 1 1 calc R . . C11 C 0.3667(3) 0.3455(3) 0.3236(3) 0.0431(15) Uani 1 1 d . . . H11 H 0.3237 0.3078 0.3047 0.052 Uiso 1 1 calc R . . C12 C 0.3580(3) 0.4360(3) 0.3125(4) 0.0485(16) Uani 1 1 d . . . H12 H 0.3101 0.4587 0.2855 0.058 Uiso 1 1 calc R . . C13 C 0.6141(3) 1.1779(3) 0.3565(3) 0.0309(12) Uani 1 1 d . . . C14 C 0.7005(3) 1.1907(3) 0.3923(3) 0.0390(15) Uani 1 1 d . . . H14 H 0.7427 1.2067 0.3530 0.047 Uiso 1 1 calc R . . C15 C 0.7206(3) 1.1810(3) 0.4754(3) 0.0380(13) Uani 1 1 d . . . H15 H 0.6780 1.1661 0.5148 0.046 Uiso 1 1 calc R . . C16 C 0.8082(3) 1.1922(3) 0.5121(4) 0.0399(14) Uani 1 1 d . . . O5 O 0.6704(4) 0.5733(6) 0.9873(5) 0.089(3) Uani 0.50 1 d P . . H5WA H 0.6808 0.5189 0.9769 0.106 Uiso 0.50 1 d PR . . H5WB H 0.7102 0.6036 0.9677 0.106 Uiso 0.50 1 d PR . . O6 O 0.6699(3) 0.4044(3) 0.9183(3) 0.131(2) Uani 1 1 d . . . H6A H 0.6648 0.3970 0.8663 0.196 Uiso 1 1 d R . . H6B H 0.6607 0.3533 0.9323 0.196 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0247(3) 0.0275(3) 0.0441(4) 0.0003(4) -0.0001(3) 0.0001(3) S1 0.0491(8) 0.0254(7) 0.0562(9) 0.0019(9) -0.0104(8) -0.0006(7) N1 0.026(2) 0.026(2) 0.039(3) 0.002(2) 0.001(2) 0.000(2) N2 0.045(3) 0.030(3) 0.061(4) 0.002(3) -0.005(3) 0.004(3) N3 0.045(3) 0.028(3) 0.063(4) 0.000(3) -0.009(3) 0.002(3) N4 0.028(2) 0.031(3) 0.034(3) 0.000(2) -0.001(2) -0.001(2) O1 0.0222(17) 0.038(2) 0.044(2) 0.0016(18) -0.0004(15) 0.0000(18) O2 0.050(2) 0.064(3) 0.034(2) 0.002(2) -0.0058(18) -0.006(2) O3 0.0313(19) 0.042(2) 0.042(2) 0.009(2) -0.0092(16) -0.0066(18) O4 0.032(2) 0.102(3) 0.047(3) 0.000(2) 0.0070(19) -0.011(2) C1 0.035(3) 0.032(3) 0.047(4) -0.003(3) -0.009(3) 0.001(3) C2 0.036(3) 0.027(3) 0.047(3) 0.004(3) -0.001(3) 0.003(3) C3 0.040(3) 0.029(4) 0.031(3) -0.001(2) 0.008(2) -0.002(3) C4 0.030(3) 0.036(4) 0.051(4) 0.003(3) -0.002(3) 0.000(3) C5 0.038(3) 0.029(4) 0.063(4) 0.005(3) -0.007(3) -0.002(3) C6 0.035(3) 0.030(4) 0.041(4) 0.002(3) 0.008(3) 0.003(3) C7 0.039(3) 0.030(4) 0.046(4) -0.001(3) -0.003(3) 0.001(3) C8 0.037(3) 0.031(4) 0.053(4) -0.009(3) 0.008(3) -0.007(3) C9 0.046(4) 0.035(4) 0.054(4) -0.008(3) -0.007(3) -0.012(3) C10 0.038(3) 0.033(3) 0.046(4) 0.004(3) -0.008(3) 0.008(3) C11 0.031(3) 0.032(4) 0.067(4) -0.005(3) -0.005(3) -0.007(3) C12 0.036(3) 0.026(3) 0.084(5) 0.001(3) -0.014(3) 0.003(3) C13 0.031(3) 0.020(3) 0.042(4) 0.004(3) -0.005(2) 0.000(3) C14 0.027(3) 0.049(4) 0.041(4) 0.006(3) 0.006(3) 0.002(2) C15 0.025(3) 0.049(4) 0.040(4) 0.005(3) 0.006(2) -0.002(3) C16 0.031(3) 0.045(4) 0.044(4) -0.008(3) -0.006(3) 0.006(3) O5 0.059(6) 0.094(7) 0.113(8) 0.004(6) 0.029(5) -0.009(5) O6 0.133(5) 0.128(5) 0.131(5) 0.010(4) -0.039(4) 0.017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.954(3) . ? Cu1 O3 1.981(3) 6_556 ? Cu1 N4 2.016(4) 1_565 ? Cu1 N1 2.018(4) . ? Cu1 O2 2.360(3) 3_655 ? S1 C6 1.714(5) . ? S1 C7 1.715(5) . ? N1 C1 1.325(5) . ? N1 C5 1.336(5) . ? N2 C6 1.302(6) . ? N2 N3 1.364(5) . ? N3 C7 1.307(6) . ? N4 C11 1.333(5) . ? N4 C10 1.336(5) . ? N4 Cu1 2.016(4) 1_545 ? O1 C13 1.255(5) . ? O2 C13 1.232(5) . ? O2 Cu1 2.360(3) 3_655 ? O3 C16 1.265(5) . ? O3 Cu1 1.981(3) 6_656 ? O4 C16 1.233(5) . ? C1 C2 1.367(6) . ? C1 H1 0.9300 . ? C2 C3 1.389(6) . ? C2 H2 0.9300 . ? C3 C4 1.380(6) . ? C3 C6 1.486(6) . ? C4 C5 1.363(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.476(6) . ? C8 C9 1.371(6) . ? C8 C12 1.389(6) . ? C9 C10 1.367(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.358(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.492(6) . ? C14 C15 1.308(6) . ? C14 H14 0.9300 . ? C15 C16 1.513(6) . ? C15 H15 0.9300 . ? O5 H5WA 0.8373 . ? O5 H5WB 0.8334 . ? O6 H6A 0.8000 . ? O6 H6B 0.8000 . ? 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 O3 146.58(13) . 6_556 ? O1 Cu1 N4 92.66(14) . 1_565 ? O3 Cu1 N4 92.44(14) 6_556 1_565 ? O1 Cu1 N1 92.80(15) . . ? O3 Cu1 N1 88.28(14) 6_556 . ? N4 Cu1 N1 168.96(15) 1_565 . ? O1 Cu1 O2 125.01(12) . 3_655 ? O3 Cu1 O2 88.36(12) 6_556 3_655 ? N4 Cu1 O2 84.43(14) 1_565 3_655 ? N1 Cu1 O2 84.58(14) . 3_655 ? C6 S1 C7 87.0(2) . . ? C1 N1 C5 115.9(4) . . ? C1 N1 Cu1 126.2(3) . . ? C5 N1 Cu1 117.9(3) . . ? C6 N2 N3 111.9(4) . . ? C7 N3 N2 112.9(4) . . ? C11 N4 C10 116.7(4) . . ? C11 N4 Cu1 118.0(3) . 1_545 ? C10 N4 Cu1 125.3(3) . 1_545 ? C13 O1 Cu1 121.7(3) . . ? C13 O2 Cu1 166.9(3) . 3_655 ? C16 O3 Cu1 112.0(3) . 6_656 ? N1 C1 C2 124.2(5) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C1 C2 C3 119.0(5) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 117.4(5) . . ? C4 C3 C6 119.9(5) . . ? C2 C3 C6 122.6(4) . . ? C5 C4 C3 118.8(5) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 124.6(5) . . ? N1 C5 H5 117.7 . . ? C4 C5 H5 117.7 . . ? N2 C6 C3 121.4(5) . . ? N2 C6 S1 114.5(4) . . ? C3 C6 S1 124.0(4) . . ? N3 C7 C8 122.4(5) . . ? N3 C7 S1 113.7(4) . . ? C8 C7 S1 124.0(4) . . ? C9 C8 C12 116.8(5) . . ? C9 C8 C7 123.6(5) . . ? C12 C8 C7 119.6(5) . . ? C10 C9 C8 119.4(5) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? N4 C10 C9 123.8(5) . . ? N4 C10 H10 118.1 . . ? C9 C10 H10 118.1 . . ? N4 C11 C12 122.7(5) . . ? N4 C11 H11 118.6 . . ? C12 C11 H11 118.6 . . ? C11 C12 C8 120.5(5) . . ? C11 C12 H12 119.8 . . ? C8 C12 H12 119.8 . . ? O2 C13 O1 125.7(4) . . ? O2 C13 C14 116.7(4) . . ? O1 C13 C14 117.5(4) . . ? C15 C14 C13 124.2(5) . . ? C15 C14 H14 117.9 . . ? C13 C14 H14 117.9 . . ? C14 C15 C16 124.6(5) . . ? C14 C15 H15 117.7 . . ? C16 C15 H15 117.7 . . ? O4 C16 O3 125.2(5) . . ? O4 C16 C15 119.0(5) . . ? O3 C16 C15 115.8(5) . . ? H5WA O5 H5WB 107.5 . . ? H6A O6 H6B 96.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 N1 C1 7.9(4) . . . . ? O3 Cu1 N1 C1 -138.7(4) 6_556 . . . ? N4 Cu1 N1 C1 127.4(7) 1_565 . . . ? O2 Cu1 N1 C1 132.8(4) 3_655 . . . ? O1 Cu1 N1 C5 -171.0(4) . . . . ? O3 Cu1 N1 C5 42.4(4) 6_556 . . . ? N4 Cu1 N1 C5 -51.5(9) 1_565 . . . ? O2 Cu1 N1 C5 -46.1(4) 3_655 . . . ? C6 N2 N3 C7 1.7(7) . . . . ? O3 Cu1 O1 C13 179.1(3) 6_556 . . . ? N4 Cu1 O1 C13 -82.4(4) 1_565 . . . ? N1 Cu1 O1 C13 87.9(4) . . . . ? O2 Cu1 O1 C13 2.6(4) 3_655 . . . ? C5 N1 C1 C2 -2.5(8) . . . . ? Cu1 N1 C1 C2 178.6(4) . . . . ? N1 C1 C2 C3 2.2(8) . . . . ? C1 C2 C3 C4 -0.9(7) . . . . ? C1 C2 C3 C6 -178.7(5) . . . . ? C2 C3 C4 C5 0.2(8) . . . . ? C6 C3 C4 C5 178.1(4) . . . . ? C1 N1 C5 C4 1.8(8) . . . . ? Cu1 N1 C5 C4 -179.2(4) . . . . ? C3 C4 C5 N1 -0.7(8) . . . . ? N3 N2 C6 C3 -179.6(4) . . . . ? N3 N2 C6 S1 -0.7(6) . . . . ? C4 C3 C6 N2 12.8(7) . . . . ? C2 C3 C6 N2 -169.5(5) . . . . ? C4 C3 C6 S1 -166.0(4) . . . . ? C2 C3 C6 S1 11.7(7) . . . . ? C7 S1 C6 N2 -0.3(4) . . . . ? C7 S1 C6 C3 178.6(4) . . . . ? N2 N3 C7 C8 177.7(4) . . . . ? N2 N3 C7 S1 -2.0(6) . . . . ? C6 S1 C7 N3 1.3(4) . . . . ? C6 S1 C7 C8 -178.4(5) . . . . ? N3 C7 C8 C9 167.5(5) . . . . ? S1 C7 C8 C9 -12.8(7) . . . . ? N3 C7 C8 C12 -11.7(8) . . . . ? S1 C7 C8 C12 167.9(4) . . . . ? C12 C8 C9 C10 0.3(8) . . . . ? C7 C8 C9 C10 -179.0(5) . . . . ? C11 N4 C10 C9 0.7(8) . . . . ? Cu1 N4 C10 C9 -178.8(4) 1_545 . . . ? C8 C9 C10 N4 -1.1(9) . . . . ? C10 N4 C11 C12 0.4(8) . . . . ? Cu1 N4 C11 C12 179.9(4) 1_545 . . . ? N4 C11 C12 C8 -1.1(9) . . . . ? C9 C8 C12 C11 0.7(8) . . . . ? C7 C8 C12 C11 -180.0(5) . . . . ? Cu1 O2 C13 O1 18(2) 3_655 . . . ? Cu1 O2 C13 C14 -160.6(13) 3_655 . . . ? Cu1 O1 C13 O2 -7.1(7) . . . . ? Cu1 O1 C13 C14 171.9(3) . . . . ? O2 C13 C14 C15 -167.4(5) . . . . ? O1 C13 C14 C15 13.5(8) . . . . ? C13 C14 C15 C16 178.9(5) . . . . ? Cu1 O3 C16 O4 -5.9(7) 6_656 . . . ? Cu1 O3 C16 C15 173.9(3) 6_656 . . . ? C14 C15 C16 O4 10.1(8) . . . . ? C14 C15 C16 O3 -169.7(5) . . . . ? 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 O5 H5WA O6 0.84 1.92 2.711(9) 156.5 . O5 H5WB O6 0.83 2.06 2.773(8) 143.9 2_665 O6 H6A N3 0.80 2.23 3.031(6) 178.8 5_666 O6 H6B O4 0.80 2.01 2.810(6) 178.4 8_746 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.512 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.091 # Attachment '6.cif' data_c _database_code_depnum_ccdc_archive 'CCDC 738472' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 Cd N4 O5 S' _chemical_formula_sum 'C15 H12 Cd N4 O5 S' _chemical_formula_weight 472.75 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 29.719(5) _cell_length_b 7.4493(13) _cell_length_c 7.5474(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1670.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.468 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6230 _exptl_absorpt_correction_T_max 0.7688 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 7887 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2627 _reflns_number_gt 2134 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. During refinement of the structure, 298 restraints were applied including thermal restraints (isor, delu and simu) which have been used in some unreasonable atoms. ; _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^)+(0.0820P)^2^+0.9770P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 2627 _refine_ls_number_parameters 205 _refine_ls_number_restraints 298 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1260 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.722102(13) -0.12915(5) 0.5063(3) 0.03337(18) Uani 1 1 d . . . S1 S 0.56053(5) 0.6895(2) 0.5083(7) 0.0492(4) Uani 1 1 d . . . O1 O 0.7620(3) 0.0342(12) 0.3106(11) 0.054(2) Uani 1 1 d . . . O2 O 0.8148(3) 0.2390(10) 0.2429(12) 0.044(2) Uani 1 1 d . . . O3 O 0.7612(3) 0.0481(11) 0.7045(10) 0.0411(18) Uani 1 1 d U . . O4 O 0.8130(3) 0.2367(10) 0.7818(11) 0.0403(18) Uani 1 1 d U . . O5 O 0.77902(13) -0.3448(6) 0.503(3) 0.0442(11) Uani 1 1 d . . . H2W H 0.7817 -0.3924 0.4016 0.066 Uiso 1 1 d R . . H1W H 0.7696 -0.4185 0.5780 0.066 Uiso 1 1 d R . . N2 N 0.5320(3) 0.4549(10) 0.2726(12) 0.0589(18) Uani 1 1 d U . . N3 N 0.4989(3) 0.5852(11) 0.2780(14) 0.0596(18) Uani 1 1 d U . . C6 C 0.5660(3) 0.4879(11) 0.3726(13) 0.0480(17) Uani 1 1 d U . . C7 C 0.5090(3) 0.7147(11) 0.3859(13) 0.0484(18) Uani 1 1 d U . . C13 C 0.7974(5) 0.1307(13) 0.673(2) 0.035(2) Uani 1 1 d U . . C14 C 0.82417(18) 0.0799(8) 0.512(2) 0.0336(12) Uani 1 1 d U . . H14A H 0.8318 -0.0466 0.5180 0.040 Uiso 1 1 calc R . . H14B H 0.8520 0.1478 0.5104 0.040 Uiso 1 1 calc R . . C15 C 0.7978(4) 0.1166(12) 0.338(2) 0.029(2) Uani 1 1 d U . . N1 N 0.66643(10) 0.0967(4) 0.4637(6) 0.0484(18) Uani 1 1 d GU . . C1 C 0.66932(10) 0.2622(4) 0.5479(6) 0.0453(19) Uani 1 1 d GU . . H1 H 0.6918 0.2828 0.6312 0.054 Uiso 1 1 calc R . . C2 C 0.63862(8) 0.3969(3) 0.5076(6) 0.0480(14) Uani 1 1 d GU . . H2 H 0.6406 0.5077 0.5640 0.058 Uiso 1 1 calc R . . C3 C 0.60503(9) 0.3661(3) 0.3831(5) 0.0484(17) Uani 1 1 d GU . . C4 C 0.60214(12) 0.2006(4) 0.2989(6) 0.0558(19) Uani 1 1 d GU . . H4 H 0.5797 0.1800 0.2156 0.067 Uiso 1 1 calc R . . C5 C 0.63284(11) 0.0658(4) 0.3392(6) 0.055(2) Uani 1 1 d GU . . H5 H 0.6309 -0.0449 0.2828 0.066 Uiso 1 1 calc R . . N5 N 0.41812(11) 1.1454(4) 0.4844(8) 0.0573(16) Uani 1 1 d GU . . C8 C 0.47771(9) 0.8652(4) 0.4200(6) 0.0422(16) Uani 1 1 d GU . . C9 C 0.46160(11) 1.1523(4) 0.5520(8) 0.052(2) Uani 1 1 d GU . . H9 H 0.4708 1.2507 0.6187 0.062 Uiso 1 1 calc R . . C10 C 0.49139(10) 1.0122(3) 0.5198(7) 0.0436(14) Uani 1 1 d GU . . H10 H 0.5205 1.0169 0.5650 0.052 Uiso 1 1 calc R . . C11 C 0.43423(10) 0.8582(5) 0.3524(7) 0.0511(19) Uani 1 1 d GU . . H11 H 0.4251 0.7599 0.2857 0.061 Uiso 1 1 calc R . . C12 C 0.40444(10) 0.9983(5) 0.3846(8) 0.061(2) Uani 1 1 d GU . . H12 H 0.3754 0.9937 0.3394 0.073 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 Cd1 0.0340(3) 0.0298(2) 0.0363(3) -0.0001(5) 0.0012(5) -0.00135(15) S1 0.0404(8) 0.0363(8) 0.0710(13) 0.009(2) 0.001(2) 0.0046(6) O1 0.074(5) 0.057(5) 0.032(5) 0.012(4) -0.002(5) -0.032(5) O2 0.041(4) 0.045(5) 0.045(5) 0.017(4) -0.011(4) -0.012(3) O3 0.036(3) 0.054(4) 0.034(4) -0.012(3) 0.014(3) -0.007(3) O4 0.043(4) 0.042(4) 0.035(4) -0.005(3) -0.003(4) -0.006(3) O5 0.047(2) 0.045(2) 0.041(3) 0.015(6) -0.002(6) 0.0017(17) N2 0.056(3) 0.055(4) 0.066(4) -0.011(3) -0.011(3) 0.015(3) N3 0.062(4) 0.051(3) 0.067(4) -0.008(3) -0.011(3) 0.015(3) C6 0.050(4) 0.045(3) 0.049(4) -0.001(3) -0.004(3) 0.000(3) C7 0.052(4) 0.039(3) 0.054(4) -0.001(3) -0.002(4) 0.002(3) C13 0.037(4) 0.037(4) 0.031(3) -0.003(3) 0.001(4) 0.002(3) C14 0.029(2) 0.037(3) 0.035(3) -0.006(4) 0.002(4) 0.001(2) C15 0.028(4) 0.026(4) 0.033(4) -0.006(3) 0.008(4) 0.001(3) N1 0.037(3) 0.042(3) 0.066(5) -0.001(3) -0.010(3) 0.002(2) C1 0.046(3) 0.033(3) 0.057(5) 0.009(3) -0.014(3) 0.006(2) C2 0.045(3) 0.035(3) 0.064(4) 0.003(4) -0.004(5) -0.002(2) C3 0.050(3) 0.039(3) 0.056(4) 0.002(3) -0.007(3) -0.001(3) C4 0.053(4) 0.054(4) 0.060(4) -0.007(3) -0.009(4) 0.007(3) C5 0.052(4) 0.050(4) 0.063(5) -0.004(3) -0.011(4) 0.005(3) N5 0.056(3) 0.059(3) 0.057(4) -0.001(3) 0.008(4) 0.021(2) C8 0.046(3) 0.040(3) 0.041(4) 0.001(3) 0.003(3) -0.001(3) C9 0.059(3) 0.046(3) 0.050(5) 0.001(3) 0.023(3) 0.008(3) C10 0.049(3) 0.041(3) 0.040(3) 0.004(4) 0.008(4) 0.003(2) C11 0.047(4) 0.056(4) 0.051(4) -0.007(3) -0.003(3) 0.008(3) C12 0.062(4) 0.061(4) 0.060(4) 0.001(4) -0.002(4) 0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O4 2.227(8) 4_644 ? Cd1 O1 2.251(8) . ? Cd1 O3 2.309(8) . ? Cd1 O2 2.315(8) 4_645 ? Cd1 O5 2.333(4) . ? Cd1 N1 2.381(2) . ? S1 C7 1.798(10) . ? S1 C6 1.825(10) . ? O1 C15 1.247(15) . ? O2 C15 1.267(14) . ? O2 Cd1 2.315(8) 4_654 ? O3 C13 1.263(16) . ? O4 C13 1.228(16) . ? O4 Cd1 2.227(8) 4_655 ? O5 H2W 0.8500 . ? O5 H1W 0.8342 . ? N2 C6 1.285(11) . ? N2 N3 1.381(11) . ? N3 C7 1.298(12) . ? C6 C3 1.475(9) . ? C7 C8 1.479(9) . ? C13 C14 1.50(2) . ? C14 C15 1.55(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? N1 C1 1.3900 . ? N1 C5 1.3900 . ? C1 C2 1.3900 . ? C1 H1 0.9300 . ? C2 C3 1.3900 . ? C2 H2 0.9300 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? N5 C9 1.3900 . ? N5 C12 1.3900 . ? C8 C11 1.3900 . ? C8 C10 1.3900 . ? C9 C10 1.3900 . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.3900 . ? C11 H11 0.9300 . ? C12 H12 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 O4 Cd1 O1 89.4(3) 4_644 . ? O4 Cd1 O3 170.2(3) 4_644 . ? O1 Cd1 O3 81.45(16) . . ? O4 Cd1 O2 100.04(16) 4_644 4_645 ? O1 Cd1 O2 170.1(3) . 4_645 ? O3 Cd1 O2 88.9(3) . 4_645 ? O4 Cd1 O5 91.4(4) 4_644 . ? O1 Cd1 O5 89.1(4) . . ? O3 Cd1 O5 92.0(4) . . ? O2 Cd1 O5 93.4(4) 4_645 . ? O4 Cd1 N1 83.6(2) 4_644 . ? O1 Cd1 N1 84.0(3) . . ? O3 Cd1 N1 91.9(2) . . ? O2 Cd1 N1 94.3(2) 4_645 . ? O5 Cd1 N1 171.5(5) . . ? C7 S1 C6 82.7(4) . . ? C15 O1 Cd1 127.3(9) . . ? C15 O2 Cd1 123.6(8) . 4_654 ? C13 O3 Cd1 125.9(8) . . ? C13 O4 Cd1 128.2(8) . 4_655 ? Cd1 O5 H2W 111.3 . . ? Cd1 O5 H1W 101.8 . . ? H2W O5 H1W 111.5 . . ? C6 N2 N3 114.0(8) . . ? C7 N3 N2 112.2(9) . . ? N2 C6 C3 122.2(7) . . ? N2 C6 S1 114.7(6) . . ? C3 C6 S1 123.1(6) . . ? N3 C7 C8 121.9(8) . . ? N3 C7 S1 116.2(7) . . ? C8 C7 S1 121.7(6) . . ? O4 C13 O3 120.7(13) . . ? O4 C13 C14 120.2(11) . . ? O3 C13 C14 118.6(10) . . ? C13 C14 C15 112.0(5) . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? O1 C15 O2 126.9(13) . . ? O1 C15 C14 119.1(10) . . ? O2 C15 C14 113.9(10) . . ? C1 N1 C5 120.0 . . ? C1 N1 Cd1 121.47(13) . . ? C5 N1 Cd1 118.26(13) . . ? C2 C1 N1 120.0 . . ? C2 C1 H1 120.0 . . ? N1 C1 H1 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 C6 118.2(4) . . ? C2 C3 C6 120.0(4) . . ? C5 C4 C3 120.0 . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 N1 120.0 . . ? C4 C5 H5 120.0 . . ? N1 C5 H5 120.0 . . ? C9 N5 C12 120.0 . . ? C11 C8 C10 120.0 . . ? C11 C8 C7 119.5(4) . . ? C10 C8 C7 120.5(4) . . ? C10 C9 N5 120.0 . . ? C10 C9 H9 120.0 . . ? N5 C9 H9 120.0 . . ? C9 C10 C8 120.0 . . ? C9 C10 H10 120.0 . . ? C8 C10 H10 120.0 . . ? C12 C11 C8 120.0 . . ? C12 C11 H11 120.0 . . ? C8 C11 H11 120.0 . . ? C11 C12 N5 120.0 . . ? C11 C12 H12 120.0 . . ? N5 C12 H12 120.0 . . ? 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 O4 Cd1 O1 C15 -161.5(11) 4_644 . . . ? O3 Cd1 O1 C15 22.0(9) . . . . ? O2 Cd1 O1 C15 35(3) 4_645 . . . ? O5 Cd1 O1 C15 -70.2(11) . . . . ? N1 Cd1 O1 C15 114.8(11) . . . . ? O4 Cd1 O3 C13 -42(2) 4_644 . . . ? O1 Cd1 O3 C13 -21.0(9) . . . . ? O2 Cd1 O3 C13 161.1(10) 4_645 . . . ? O5 Cd1 O3 C13 67.8(10) . . . . ? N1 Cd1 O3 C13 -104.6(10) . . . . ? C6 N2 N3 C7 -0.7(13) . . . . ? N3 N2 C6 C3 -179.1(8) . . . . ? N3 N2 C6 S1 4.1(11) . . . . ? C7 S1 C6 N2 -4.6(8) . . . . ? C7 S1 C6 C3 178.7(7) . . . . ? N2 N3 C7 C8 -177.1(7) . . . . ? N2 N3 C7 S1 -3.1(12) . . . . ? C6 S1 C7 N3 4.3(9) . . . . ? C6 S1 C7 C8 178.2(7) . . . . ? Cd1 O4 C13 O3 -18.8(18) 4_655 . . . ? Cd1 O4 C13 C14 168.9(7) 4_655 . . . ? Cd1 O3 C13 O4 172.2(8) . . . . ? Cd1 O3 C13 C14 -15.4(17) . . . . ? O4 C13 C14 C15 -124.4(12) . . . . ? O3 C13 C14 C15 63.2(13) . . . . ? Cd1 O1 C15 O2 -162.9(10) . . . . ? Cd1 O1 C15 C14 12.6(16) . . . . ? Cd1 O2 C15 O1 8.7(19) 4_654 . . . ? Cd1 O2 C15 C14 -167.0(6) 4_654 . . . ? C13 C14 C15 O1 -62.5(11) . . . . ? C13 C14 C15 O2 113.5(11) . . . . ? O4 Cd1 N1 C1 -169.4(3) 4_644 . . . ? O1 Cd1 N1 C1 -79.3(3) . . . . ? O3 Cd1 N1 C1 1.9(3) . . . . ? O2 Cd1 N1 C1 90.9(3) 4_645 . . . ? O5 Cd1 N1 C1 -115.3(13) . . . . ? O4 Cd1 N1 C5 4.7(3) 4_644 . . . ? O1 Cd1 N1 C5 94.8(3) . . . . ? O3 Cd1 N1 C5 176.0(3) . . . . ? O2 Cd1 N1 C5 -94.9(3) 4_645 . . . ? O5 Cd1 N1 C5 58.8(13) . . . . ? C5 N1 C1 C2 0.0 . . . . ? Cd1 N1 C1 C2 174.01(16) . . . . ? N1 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C1 C2 C3 C6 164.4(4) . . . . ? N2 C6 C3 C4 -8.1(10) . . . . ? S1 C6 C3 C4 168.4(4) . . . . ? N2 C6 C3 C2 -172.8(7) . . . . ? S1 C6 C3 C2 3.7(8) . . . . ? C2 C3 C4 C5 0.0 . . . . ? C6 C3 C4 C5 -164.6(4) . . . . ? C3 C4 C5 N1 0.0 . . . . ? C1 N1 C5 C4 0.0 . . . . ? Cd1 N1 C5 C4 -174.20(15) . . . . ? N3 C7 C8 C11 8.0(11) . . . . ? S1 C7 C8 C11 -165.7(4) . . . . ? N3 C7 C8 C10 -172.5(8) . . . . ? S1 C7 C8 C10 13.9(8) . . . . ? C12 N5 C9 C10 0.0 . . . . ? N5 C9 C10 C8 0.0 . . . . ? C11 C8 C10 C9 0.0 . . . . ? C7 C8 C10 C9 -179.6(4) . . . . ? C10 C8 C11 C12 0.0 . . . . ? C7 C8 C11 C12 179.6(4) . . . . ? C8 C11 C12 N5 0.0 . . . . ? C9 N5 C12 C11 0.0 . . . . ? 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 O5 H2W O3 0.85 2.01 2.674(19) 134.7 4_644 O5 H1W O1 0.83 2.02 2.770(19) 148.8 4_645 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.204 _refine_diff_density_min -0.676 _refine_diff_density_rms 0.122 # Attachment '7.cif' data_xb2824m _database_code_depnum_ccdc_archive 'CCDC 738473' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 Cd N4 O4 S' _chemical_formula_sum 'C16 H12 Cd N4 O4 S' _chemical_formula_weight 468.76 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' Cd Cd -0.8075 1.2024 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5795(7) _cell_length_b 11.5813(8) _cell_length_c 13.6314(9) _cell_angle_alpha 90.00 _cell_angle_beta 105.9360(10) _cell_angle_gamma 90.00 _cell_volume 1605.99(19) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.939 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.522 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7405 _exptl_absorpt_correction_T_max 0.8267 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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_% 0 _diffrn_reflns_number 7837 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2888 _reflns_number_gt 2664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0479P)^2^+0.0587P] 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 2888 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0226 _refine_ls_R_factor_gt 0.0207 _refine_ls_wR_factor_ref 0.0608 _refine_ls_wR_factor_gt 0.0597 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.431287(13) 0.560688(11) 0.102740(10) 0.02256(8) Uani 1 1 d . . . S1 S -0.12771(5) 0.09149(5) 0.04896(4) 0.02896(13) Uani 1 1 d . . . N1 N 0.28739(16) 0.39603(15) 0.09780(13) 0.0262(4) Uani 1 1 d . . . N2 N -0.42730(16) -0.27520(15) 0.10475(13) 0.0255(4) Uani 1 1 d . . . N3 N 0.0624(2) 0.06078(14) 0.20817(16) 0.0342(5) Uani 1 1 d . . . N4 N -0.02973(18) -0.01976(17) 0.21377(14) 0.0349(4) Uani 1 1 d . . . O1 O 0.37497(14) 0.65189(13) 0.24116(11) 0.0327(3) Uani 1 1 d . . . O2 O 0.24901(15) 0.67901(13) 0.08498(11) 0.0312(3) Uani 1 1 d . . . O3 O 0.38703(16) 0.94500(12) 0.26025(12) 0.0325(4) Uani 1 1 d . . . O4 O 0.40897(15) 0.94435(11) 0.42510(11) 0.0294(4) Uani 1 1 d . . . C1 C 0.1568(2) 0.40882(19) 0.06248(18) 0.0319(5) Uani 1 1 d . . . H1 H 0.1244 0.4798 0.0347 0.038 Uiso 1 1 calc R . . C2 C 0.0674(2) 0.32217(18) 0.06503(16) 0.0298(5) Uani 1 1 d . . . H2 H -0.0224 0.3345 0.0386 0.036 Uiso 1 1 calc R . . C3 C 0.11471(19) 0.21668(17) 0.10790(14) 0.0241(4) Uani 1 1 d . . . C4 C 0.25022(19) 0.20042(18) 0.14073(15) 0.0273(4) Uani 1 1 d . . . H4 H 0.2852 0.1294 0.1664 0.033 Uiso 1 1 calc R . . C5 C 0.3318(2) 0.29185(17) 0.13442(15) 0.0269(4) Uani 1 1 d . . . H5 H 0.4222 0.2804 0.1568 0.032 Uiso 1 1 calc R . . C6 C 0.02656(19) 0.12460(17) 0.12628(16) 0.0254(4) Uani 1 1 d . . . C7 C -0.13428(19) -0.01414(17) 0.13630(15) 0.0252(4) Uani 1 1 d . . . C8 C -0.4610(2) -0.16406(18) 0.10007(17) 0.0325(5) Uani 1 1 d . . . H8 H -0.5491 -0.1459 0.0909 0.039 Uiso 1 1 calc R . . C9 C -0.3727(2) -0.07380(17) 0.10797(19) 0.0329(5) Uani 1 1 d . . . H9 H -0.4011 0.0025 0.1028 0.039 Uiso 1 1 calc R . . C10 C -0.24109(19) -0.10061(17) 0.12384(15) 0.0248(4) Uani 1 1 d . . . C11 C -0.2045(2) -0.21605(17) 0.13014(15) 0.0266(4) Uani 1 1 d . . . H11 H -0.1168 -0.2367 0.1412 0.032 Uiso 1 1 calc R . . C12 C -0.2995(2) -0.29918(17) 0.11988(15) 0.0279(4) Uani 1 1 d . . . H12 H -0.2739 -0.3762 0.1236 0.033 Uiso 1 1 calc R . . C13 C 0.27734(19) 0.69744(17) 0.17981(15) 0.0243(4) Uani 1 1 d . . . C14 C 0.1867(2) 0.77381(19) 0.21895(16) 0.0304(5) Uani 1 1 d . . . H14A H 0.1087 0.7297 0.2189 0.037 Uiso 1 1 calc R . . H14B H 0.1592 0.8375 0.1717 0.037 Uiso 1 1 calc R . . C15 C 0.2438(2) 0.82292(18) 0.32459(15) 0.0277(4) Uani 1 1 d . . . H15A H 0.1735 0.8596 0.3463 0.033 Uiso 1 1 calc R . . H15B H 0.2768 0.7596 0.3711 0.033 Uiso 1 1 calc R . . C16 C 0.35247(19) 0.90896(17) 0.33404(15) 0.0216(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02057(11) 0.01811(12) 0.03057(12) -0.00227(5) 0.00963(8) -0.00280(5) S1 0.0259(3) 0.0248(3) 0.0348(3) 0.0043(2) 0.0059(2) -0.0065(2) N1 0.0226(9) 0.0240(9) 0.0329(9) 0.0003(8) 0.0091(7) -0.0061(7) N2 0.0231(9) 0.0246(9) 0.0295(9) -0.0027(7) 0.0081(7) -0.0064(7) N3 0.0266(10) 0.0298(11) 0.0435(11) 0.0083(8) 0.0051(9) -0.0112(7) N4 0.0281(10) 0.0313(10) 0.0423(10) 0.0078(8) 0.0045(8) -0.0112(8) O1 0.0304(8) 0.0325(8) 0.0349(8) 0.0021(6) 0.0084(7) 0.0089(7) O2 0.0306(8) 0.0320(8) 0.0303(7) -0.0060(6) 0.0070(6) 0.0028(7) O3 0.0346(9) 0.0328(9) 0.0342(8) 0.0038(6) 0.0163(7) -0.0036(6) O4 0.0297(9) 0.0280(9) 0.0293(8) -0.0042(6) 0.0057(7) -0.0056(6) C1 0.0282(12) 0.0207(10) 0.0472(13) 0.0058(10) 0.0112(10) 0.0006(9) C2 0.0217(10) 0.0245(11) 0.0433(12) 0.0042(9) 0.0089(9) -0.0009(8) C3 0.0237(10) 0.0205(10) 0.0296(10) -0.0022(8) 0.0099(8) -0.0059(8) C4 0.0268(11) 0.0223(10) 0.0327(10) 0.0052(8) 0.0080(9) -0.0001(8) C5 0.0223(10) 0.0260(11) 0.0314(10) 0.0012(8) 0.0059(8) -0.0030(8) C6 0.0215(10) 0.0197(10) 0.0363(11) -0.0032(8) 0.0100(8) -0.0027(8) C7 0.0237(10) 0.0183(10) 0.0350(11) 0.0010(8) 0.0106(9) -0.0033(8) C8 0.0200(10) 0.0306(12) 0.0469(13) -0.0028(10) 0.0090(9) -0.0027(9) C9 0.0265(12) 0.0199(10) 0.0522(14) 0.0003(9) 0.0109(11) -0.0011(8) C10 0.0245(10) 0.0206(10) 0.0291(10) -0.0005(8) 0.0072(8) -0.0071(9) C11 0.0211(10) 0.0229(10) 0.0365(11) 0.0005(9) 0.0093(8) -0.0016(8) C12 0.0275(11) 0.0211(10) 0.0357(11) -0.0024(9) 0.0096(9) -0.0031(8) C13 0.0206(10) 0.0179(10) 0.0354(11) -0.0035(8) 0.0093(8) -0.0054(8) C14 0.0207(10) 0.0321(11) 0.0379(11) -0.0093(9) 0.0070(8) -0.0002(9) C15 0.0286(11) 0.0261(11) 0.0318(10) -0.0045(9) 0.0140(9) -0.0066(9) C16 0.0201(10) 0.0171(9) 0.0277(10) 0.0001(8) 0.0068(8) 0.0044(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 Cd1 O4 2.2733(15) 2_645 ? Cd1 O2 2.3236(15) . ? Cd1 O4 2.3682(15) 4_575 ? Cd1 O1 2.3766(14) . ? Cd1 N2 2.4143(16) 1_665 ? Cd1 N1 2.4294(16) . ? Cd1 O3 2.6470(16) 2_645 ? S1 C7 1.722(2) . ? S1 C6 1.725(2) . ? N1 C1 1.340(3) . ? N1 C5 1.340(3) . ? N2 C8 1.333(3) . ? N2 C12 1.339(3) . ? N2 Cd1 2.4143(16) 1_445 ? N3 C6 1.305(3) . ? N3 N4 1.366(2) . ? N4 C7 1.304(3) . ? O1 C13 1.253(3) . ? O2 C13 1.262(2) . ? O3 C16 1.233(2) . ? O3 Cd1 2.6470(16) 2_655 ? O4 C16 1.288(2) . ? O4 Cd1 2.2733(15) 2_655 ? O4 Cd1 2.3682(15) 4_576 ? C1 C2 1.386(3) . ? C1 H1 0.9300 . ? C2 C3 1.387(3) . ? C2 H2 0.9300 . ? C3 C4 1.392(3) . ? C3 C6 1.483(3) . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C10 1.484(3) . ? C8 C9 1.386(3) . ? C8 H8 0.9300 . ? C9 C10 1.385(3) . ? C9 H9 0.9300 . ? C10 C11 1.388(3) . ? C11 C12 1.371(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.506(3) . ? C14 C15 1.511(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.500(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? 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 O4 Cd1 O2 165.00(5) 2_645 . ? O4 Cd1 O4 71.62(6) 2_645 4_575 ? O2 Cd1 O4 93.50(5) . 4_575 ? O4 Cd1 O1 139.10(5) 2_645 . ? O2 Cd1 O1 55.86(5) . . ? O4 Cd1 O1 147.82(5) 4_575 . ? O4 Cd1 N2 88.95(5) 2_645 1_665 ? O2 Cd1 N2 91.77(5) . 1_665 ? O4 Cd1 N2 85.33(5) 4_575 1_665 ? O1 Cd1 N2 86.03(5) . 1_665 ? O4 Cd1 N1 91.09(5) 2_645 . ? O2 Cd1 N1 87.95(5) . . ? O4 Cd1 N1 93.81(6) 4_575 . ? O1 Cd1 N1 94.53(5) . . ? N2 Cd1 N1 179.08(5) 1_665 . ? O4 Cd1 O3 52.32(5) 2_645 2_645 ? O2 Cd1 O3 142.48(5) . 2_645 ? O4 Cd1 O3 123.93(5) 4_575 2_645 ? O1 Cd1 O3 87.51(5) . 2_645 ? N2 Cd1 O3 93.60(5) 1_665 2_645 ? N1 Cd1 O3 87.16(5) . 2_645 ? C7 S1 C6 86.93(10) . . ? C1 N1 C5 117.04(17) . . ? C1 N1 Cd1 119.95(14) . . ? C5 N1 Cd1 122.90(13) . . ? C8 N2 C12 116.94(17) . . ? C8 N2 Cd1 127.09(13) . 1_445 ? C12 N2 Cd1 115.76(13) . 1_445 ? C6 N3 N4 112.97(18) . . ? C7 N4 N3 112.34(17) . . ? C13 O1 Cd1 89.86(12) . . ? C13 O2 Cd1 92.07(12) . . ? C16 O3 Cd1 85.20(12) . 2_655 ? C16 O4 Cd1 101.38(12) . 2_655 ? C16 O4 Cd1 150.14(13) . 4_576 ? Cd1 O4 Cd1 108.38(6) 2_655 4_576 ? N1 C1 C2 123.6(2) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 118.58(19) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 118.36(18) . . ? C2 C3 C6 122.26(18) . . ? C4 C3 C6 119.23(18) . . ? C5 C4 C3 118.78(19) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 123.43(18) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? N3 C6 C3 120.22(18) . . ? N3 C6 S1 113.61(15) . . ? C3 C6 S1 126.16(15) . . ? N4 C7 C10 120.58(18) . . ? N4 C7 S1 114.14(15) . . ? C10 C7 S1 125.04(15) . . ? N2 C8 C9 124.0(2) . . ? N2 C8 H8 118.0 . . ? C9 C8 H8 118.0 . . ? C10 C9 C8 118.05(19) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? C9 C10 C11 118.48(18) . . ? C9 C10 C7 124.61(19) . . ? C11 C10 C7 116.91(18) . . ? C12 C11 C10 119.10(19) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? N2 C12 C11 123.41(19) . . ? N2 C12 H12 118.3 . . ? C11 C12 H12 118.3 . . ? O1 C13 O2 122.19(18) . . ? O1 C13 C14 119.95(18) . . ? O2 C13 C14 117.83(18) . . ? C13 C14 C15 115.58(17) . . ? C13 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? C13 C14 H14B 108.4 . . ? C15 C14 H14B 108.4 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C14 115.34(17) . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15B 108.4 . . ? C14 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? O3 C16 O4 121.02(19) . . ? O3 C16 C15 123.13(18) . . ? O4 C16 C15 115.85(17) . . ? 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 O4 Cd1 N1 C1 -148.18(16) 2_645 . . . ? O2 Cd1 N1 C1 16.85(16) . . . . ? O4 Cd1 N1 C1 -76.53(16) 4_575 . . . ? O1 Cd1 N1 C1 72.37(16) . . . . ? N2 Cd1 N1 C1 -55(4) 1_665 . . . ? O3 Cd1 N1 C1 159.64(16) 2_645 . . . ? O4 Cd1 N1 C5 35.62(16) 2_645 . . . ? O2 Cd1 N1 C5 -159.35(15) . . . . ? O4 Cd1 N1 C5 107.27(15) 4_575 . . . ? O1 Cd1 N1 C5 -103.83(15) . . . . ? N2 Cd1 N1 C5 128(3) 1_665 . . . ? O3 Cd1 N1 C5 -16.56(15) 2_645 . . . ? C6 N3 N4 C7 -0.8(3) . . . . ? O4 Cd1 O1 C13 177.85(11) 2_645 . . . ? O2 Cd1 O1 C13 -0.79(11) . . . . ? O4 Cd1 O1 C13 19.34(17) 4_575 . . . ? N2 Cd1 O1 C13 94.06(12) 1_665 . . . ? N1 Cd1 O1 C13 -85.21(12) . . . . ? O3 Cd1 O1 C13 -172.16(12) 2_645 . . . ? O4 Cd1 O2 C13 -175.76(18) 2_645 . . . ? O4 Cd1 O2 C13 -168.64(12) 4_575 . . . ? O1 Cd1 O2 C13 0.78(11) . . . . ? N2 Cd1 O2 C13 -83.21(12) 1_665 . . . ? N1 Cd1 O2 C13 97.66(12) . . . . ? O3 Cd1 O2 C13 15.03(16) 2_645 . . . ? C5 N1 C1 C2 2.1(3) . . . . ? Cd1 N1 C1 C2 -174.32(17) . . . . ? N1 C1 C2 C3 1.1(3) . . . . ? C1 C2 C3 C4 -3.9(3) . . . . ? C1 C2 C3 C6 171.78(19) . . . . ? C2 C3 C4 C5 3.5(3) . . . . ? C6 C3 C4 C5 -172.30(18) . . . . ? C1 N1 C5 C4 -2.5(3) . . . . ? Cd1 N1 C5 C4 173.78(15) . . . . ? C3 C4 C5 N1 -0.3(3) . . . . ? N4 N3 C6 C3 179.91(18) . . . . ? N4 N3 C6 S1 1.0(2) . . . . ? C2 C3 C6 N3 -142.1(2) . . . . ? C4 C3 C6 N3 33.5(3) . . . . ? C2 C3 C6 S1 36.6(3) . . . . ? C4 C3 C6 S1 -147.76(17) . . . . ? C7 S1 C6 N3 -0.72(17) . . . . ? C7 S1 C6 C3 -179.56(18) . . . . ? N3 N4 C7 C10 174.92(19) . . . . ? N3 N4 C7 S1 0.2(2) . . . . ? C6 S1 C7 N4 0.27(18) . . . . ? C6 S1 C7 C10 -174.16(18) . . . . ? C12 N2 C8 C9 1.2(3) . . . . ? Cd1 N2 C8 C9 175.81(17) 1_445 . . . ? N2 C8 C9 C10 -1.4(4) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C8 C9 C10 C7 -178.5(2) . . . . ? N4 C7 C10 C9 128.6(2) . . . . ? S1 C7 C10 C9 -57.3(3) . . . . ? N4 C7 C10 C11 -50.5(3) . . . . ? S1 C7 C10 C11 123.59(19) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C7 C10 C11 C12 179.52(19) . . . . ? C8 N2 C12 C11 -0.2(3) . . . . ? Cd1 N2 C12 C11 -175.41(16) 1_445 . . . ? C10 C11 C12 N2 -0.6(3) . . . . ? Cd1 O1 C13 O2 1.4(2) . . . . ? Cd1 O1 C13 C14 179.26(16) . . . . ? Cd1 O2 C13 O1 -1.5(2) . . . . ? Cd1 O2 C13 C14 -179.34(16) . . . . ? O1 C13 C14 C15 20.2(3) . . . . ? O2 C13 C14 C15 -161.88(18) . . . . ? C13 C14 C15 C16 67.5(2) . . . . ? Cd1 O3 C16 O4 2.90(18) 2_655 . . . ? Cd1 O3 C16 C15 -177.30(18) 2_655 . . . ? Cd1 O4 C16 O3 -3.4(2) 2_655 . . . ? Cd1 O4 C16 O3 -178.63(17) 4_576 . . . ? Cd1 O4 C16 C15 176.75(14) 2_655 . . . ? Cd1 O4 C16 C15 1.6(4) 4_576 . . . ? C14 C15 C16 O3 5.6(3) . . . . ? C14 C15 C16 O4 -174.61(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.298 _refine_diff_density_min -0.881 _refine_diff_density_rms 0.127 # Attachment '8.cif' data_xb2693m _database_code_depnum_ccdc_archive 'CCDC 738474' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 Cd N4 O5 S' _chemical_formula_weight 498.78 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' Cd Cd -0.8075 1.2024 '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' H H 0.0000 0.0000 '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 8.8599(19) _cell_length_b 9.647(2) _cell_length_c 11.620(3) _cell_angle_alpha 87.575(4) _cell_angle_beta 80.901(4) _cell_angle_gamma 70.326(3) _cell_volume 923.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.794 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.334 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7081 _exptl_absorpt_correction_T_max 0.8510 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4689 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0720 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.20 _reflns_number_total 3250 _reflns_number_gt 2354 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1095P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3250 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1721 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Cd1 Cd 0.11166(6) 0.10333(6) -0.10792(5) 0.0313(3) Uani 1 1 d . . . S1 S 0.0515(3) 0.6351(2) 0.39047(19) 0.0381(5) Uani 1 1 d . . . N1 N 0.1185(7) 0.2290(7) 0.0546(6) 0.0351(16) Uani 1 1 d . . . N2 N 0.2986(9) 0.4054(8) 0.3942(8) 0.056(2) Uani 1 1 d . . . N3 N 0.3014(8) 0.4958(8) 0.4801(8) 0.054(2) Uani 1 1 d . . . N4 N 0.1305(8) 0.9420(7) 0.7453(6) 0.0377(17) Uani 1 1 d . . . O1 O 0.2428(6) 0.2394(7) -0.2300(6) 0.0491(16) Uani 1 1 d . . . O2 O 0.4087(7) 0.0532(7) -0.1504(6) 0.0477(16) Uani 1 1 d . . . O3 O 0.8529(7) 0.2687(8) -0.1412(6) 0.061(2) Uani 1 1 d . . . O4 O 0.8387(7) 0.1019(7) -0.0147(6) 0.0533(16) Uiso 1 1 d . . . C1 C 0.0011(10) 0.3597(9) 0.0975(8) 0.042(2) Uani 1 1 d . . . H1 H -0.0928 0.3954 0.0636 0.050 Uiso 1 1 calc R . . C2 C 0.0165(10) 0.4364(9) 0.1847(7) 0.038(2) Uani 1 1 d . . . H2 H -0.0638 0.5250 0.2092 0.046 Uiso 1 1 calc R . . C3 C 0.1548(9) 0.3824(9) 0.2395(7) 0.0344(19) Uani 1 1 d . . . C4 C 0.2678(9) 0.2544(9) 0.2021(8) 0.0363(19) Uani 1 1 d . . . H4 H 0.3597 0.2159 0.2379 0.044 Uiso 1 1 calc R . . C5 C 0.2478(9) 0.1802(8) 0.1106(8) 0.040(2) Uani 1 1 d . . . H5 H 0.3279 0.0914 0.0861 0.049 Uiso 1 1 calc R . . C6 C 0.1759(9) 0.4643(9) 0.3402(8) 0.038(2) Uani 1 1 d . . . C7 C 0.1805(10) 0.6216(9) 0.4903(8) 0.040(2) Uani 1 1 d . . . C8 C 0.1633(9) 0.7304(9) 0.5746(7) 0.0351(19) Uani 1 1 d . . . C9 C 0.2889(10) 0.7197(11) 0.6365(9) 0.054(3) Uani 1 1 d . . . H9 H 0.3862 0.6416 0.6235 0.065 Uiso 1 1 calc R . . C10 C 0.2644(11) 0.8298(10) 0.7189(8) 0.050(3) Uani 1 1 d . . . H10 H 0.3502 0.8229 0.7582 0.060 Uiso 1 1 calc R . . C11 C 0.0113(9) 0.9533(9) 0.6831(7) 0.0360(19) Uani 1 1 d . . . H11 H -0.0827 1.0348 0.6971 0.043 Uiso 1 1 calc R . . C12 C 0.0190(10) 0.8545(8) 0.6020(8) 0.041(2) Uani 1 1 d . . . H12 H -0.0694 0.8670 0.5639 0.049 Uiso 1 1 calc R . . C13 C 0.3832(9) 0.1671(9) -0.2071(7) 0.0328(18) Uani 1 1 d . . . C14 C 0.5138(10) 0.2334(11) -0.2502(8) 0.054(3) Uani 1 1 d . . . H14A H 0.4923 0.2845 -0.3226 0.064 Uiso 1 1 calc R . . H14B H 0.6184 0.1559 -0.2649 0.064 Uiso 1 1 calc R . . C15 C 0.5173(11) 0.3439(10) -0.1564(11) 0.064(3) Uani 1 1 d . . . H15A H 0.5785 0.4047 -0.1932 0.077 Uiso 1 1 calc R . . H15B H 0.4070 0.4082 -0.1316 0.077 Uiso 1 1 calc R . . C16 C 0.5889(10) 0.2762(10) -0.0494(9) 0.050(2) Uani 1 1 d . . . H16A H 0.5562 0.3510 0.0115 0.059 Uiso 1 1 calc R . . H16B H 0.5450 0.1993 -0.0215 0.059 Uiso 1 1 calc R . . C17 C 0.7702(9) 0.2122(8) -0.0705(8) 0.038(2) Uani 1 1 d . . . O5 O 0.3369(13) 0.1039(13) 0.5096(10) 0.136(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0333(4) 0.0323(4) 0.0303(4) -0.0056(2) -0.0073(2) -0.0118(2) S1 0.0480(12) 0.0342(10) 0.0309(13) -0.0080(9) -0.0116(10) -0.0088(9) N1 0.037(4) 0.033(3) 0.037(5) -0.010(3) -0.005(3) -0.012(3) N2 0.049(4) 0.054(5) 0.061(6) -0.033(4) -0.020(4) -0.005(4) N3 0.041(4) 0.049(4) 0.068(6) -0.029(4) -0.023(4) -0.001(3) N4 0.037(4) 0.041(4) 0.038(5) -0.012(3) -0.008(3) -0.015(3) O1 0.031(3) 0.056(4) 0.063(5) 0.015(3) -0.016(3) -0.017(3) O2 0.041(3) 0.050(4) 0.052(5) 0.001(3) -0.013(3) -0.014(3) O3 0.028(3) 0.088(5) 0.069(5) 0.041(4) -0.017(3) -0.023(3) C1 0.041(4) 0.034(4) 0.052(6) -0.002(4) -0.018(4) -0.010(4) C2 0.043(5) 0.038(4) 0.035(6) 0.001(4) -0.016(4) -0.011(4) C3 0.039(4) 0.039(4) 0.035(5) 0.009(4) -0.015(4) -0.022(4) C4 0.025(4) 0.045(5) 0.040(6) 0.004(4) -0.012(4) -0.010(3) C5 0.032(4) 0.024(4) 0.065(7) -0.008(4) -0.016(4) -0.006(3) C6 0.037(4) 0.035(4) 0.044(6) -0.006(4) -0.009(4) -0.013(4) C7 0.043(5) 0.040(5) 0.047(6) -0.003(4) -0.012(4) -0.022(4) C8 0.033(4) 0.045(5) 0.028(5) -0.004(4) -0.001(4) -0.015(4) C9 0.034(4) 0.058(6) 0.066(8) -0.022(5) -0.021(5) -0.002(4) C10 0.050(5) 0.052(5) 0.041(6) -0.039(5) -0.005(4) -0.005(4) C11 0.033(4) 0.044(5) 0.030(5) -0.003(4) -0.011(4) -0.008(3) C12 0.044(5) 0.035(4) 0.048(6) 0.002(4) -0.019(4) -0.016(4) C13 0.028(4) 0.035(4) 0.031(5) -0.012(4) -0.004(4) -0.004(3) C14 0.039(5) 0.085(7) 0.038(6) 0.005(5) -0.007(4) -0.023(5) C15 0.039(5) 0.038(5) 0.121(11) -0.002(6) -0.021(6) -0.017(4) C16 0.037(4) 0.050(5) 0.062(7) -0.016(5) -0.001(4) -0.016(4) C17 0.039(4) 0.035(4) 0.043(6) 0.001(4) -0.019(4) -0.011(4) O5 0.123(9) 0.145(10) 0.146(12) 0.040(8) -0.070(8) -0.035(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 Cd1 N1 2.306(6) . ? Cd1 N4 2.306(6) 1_544 ? Cd1 O1 2.331(6) . ? Cd1 O4 2.348(7) 2_655 ? Cd1 O3 2.391(6) 1_455 ? Cd1 O2 2.481(6) . ? Cd1 O4 2.493(6) 1_455 ? S1 C6 1.711(8) . ? S1 C7 1.724(8) . ? N1 C5 1.344(10) . ? N1 C1 1.388(10) . ? N2 C6 1.291(11) . ? N2 N3 1.362(10) . ? N3 C7 1.316(10) . ? N4 C10 1.312(11) . ? N4 C11 1.344(10) . ? N4 Cd1 2.306(6) 1_566 ? O1 C13 1.269(9) . ? O2 C13 1.229(10) . ? O3 C17 1.244(10) . ? O3 Cd1 2.391(6) 1_655 ? O4 C17 1.247(10) . ? O4 Cd1 2.348(7) 2_655 ? O4 Cd1 2.493(6) 1_655 ? C1 C2 1.329(11) . ? C1 H1 0.9300 . ? C2 C3 1.402(11) . ? C2 H2 0.9300 . ? C3 C4 1.338(11) . ? C3 C6 1.509(11) . ? C4 C5 1.372(11) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.420(11) . ? C8 C9 1.391(12) . ? C8 C12 1.429(11) . ? C9 C10 1.399(12) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.347(11) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.512(11) . ? C14 C15 1.567(13) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.509(14) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.497(11) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? 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 Cd1 N4 170.1(2) . 1_544 ? N1 Cd1 O1 91.6(2) . . ? N4 Cd1 O1 93.4(2) 1_544 . ? N1 Cd1 O4 84.5(2) . 2_655 ? N4 Cd1 O4 86.3(2) 1_544 2_655 ? O1 Cd1 O4 142.2(2) . 2_655 ? N1 Cd1 O3 94.3(2) . 1_455 ? N4 Cd1 O3 94.1(3) 1_544 1_455 ? O1 Cd1 O3 90.9(2) . 1_455 ? O4 Cd1 O3 126.9(2) 2_655 1_455 ? N1 Cd1 O2 85.8(2) . . ? N4 Cd1 O2 90.3(2) 1_544 . ? O1 Cd1 O2 53.8(2) . . ? O4 Cd1 O2 88.4(2) 2_655 . ? O3 Cd1 O2 144.6(2) 1_455 . ? N1 Cd1 O4 87.6(2) . 1_455 ? N4 Cd1 O4 93.5(2) 1_544 1_455 ? O1 Cd1 O4 142.9(2) . 1_455 ? O4 Cd1 O4 74.6(2) 2_655 1_455 ? O3 Cd1 O4 52.3(2) 1_455 1_455 ? O2 Cd1 O4 162.3(2) . 1_455 ? C6 S1 C7 87.4(4) . . ? C5 N1 C1 115.4(7) . . ? C5 N1 Cd1 119.6(5) . . ? C1 N1 Cd1 124.9(5) . . ? C6 N2 N3 111.6(7) . . ? C7 N3 N2 114.1(7) . . ? C10 N4 C11 116.0(7) . . ? C10 N4 Cd1 119.6(5) . 1_566 ? C11 N4 Cd1 124.4(5) . 1_566 ? C13 O1 Cd1 94.9(5) . . ? C13 O2 Cd1 88.9(5) . . ? C17 O3 Cd1 96.4(5) . 1_655 ? C17 O4 Cd1 163.1(6) . 2_655 ? C17 O4 Cd1 91.4(5) . 1_655 ? Cd1 O4 Cd1 105.4(2) 2_655 1_655 ? C2 C1 N1 123.2(7) . . ? C2 C1 H1 118.4 . . ? N1 C1 H1 118.4 . . ? C1 C2 C3 119.4(8) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 118.7(8) . . ? C4 C3 C6 120.1(7) . . ? C2 C3 C6 121.2(7) . . ? C3 C4 C5 119.8(7) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 123.4(7) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? N2 C6 C3 119.4(7) . . ? N2 C6 S1 115.0(6) . . ? C3 C6 S1 125.7(6) . . ? N3 C7 C8 122.3(8) . . ? N3 C7 S1 112.0(6) . . ? C8 C7 S1 125.8(6) . . ? C9 C8 C7 120.7(8) . . ? C9 C8 C12 116.2(7) . . ? C7 C8 C12 123.1(7) . . ? C8 C9 C10 118.0(8) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? N4 C10 C9 125.5(8) . . ? N4 C10 H10 117.3 . . ? C9 C10 H10 117.3 . . ? N4 C11 C12 124.4(7) . . ? N4 C11 H11 117.8 . . ? C12 C11 H11 117.8 . . ? C11 C12 C8 119.8(7) . . ? C11 C12 H12 120.1 . . ? C8 C12 H12 120.1 . . ? O2 C13 O1 121.6(7) . . ? O2 C13 C14 122.8(7) . . ? O1 C13 C14 115.5(8) . . ? C13 C14 C15 109.7(8) . . ? C13 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? C13 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C16 C15 C14 116.1(8) . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15A 108.3 . . ? C16 C15 H15B 108.3 . . ? C14 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C17 C16 C15 113.4(8) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? O3 C17 O4 119.8(7) . . ? O3 C17 C16 121.1(8) . . ? O4 C17 C16 119.0(8) . . ? 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 N4 Cd1 N1 C5 32.0(16) 1_544 . . . ? O1 Cd1 N1 C5 -88.3(6) . . . . ? O4 Cd1 N1 C5 54.1(6) 2_655 . . . ? O3 Cd1 N1 C5 -179.2(6) 1_455 . . . ? O2 Cd1 N1 C5 -34.7(6) . . . . ? O4 Cd1 N1 C5 128.8(6) 1_455 . . . ? N4 Cd1 N1 C1 -152.0(12) 1_544 . . . ? O1 Cd1 N1 C1 87.8(7) . . . . ? O4 Cd1 N1 C1 -129.9(7) 2_655 . . . ? O3 Cd1 N1 C1 -3.2(7) 1_455 . . . ? O2 Cd1 N1 C1 141.3(7) . . . . ? O4 Cd1 N1 C1 -55.1(7) 1_455 . . . ? C6 N2 N3 C7 0.3(13) . . . . ? N1 Cd1 O1 C13 78.8(5) . . . . ? N4 Cd1 O1 C13 -92.6(5) 1_544 . . . ? O4 Cd1 O1 C13 -4.4(7) 2_655 . . . ? O3 Cd1 O1 C13 173.2(5) 1_455 . . . ? O2 Cd1 O1 C13 -4.8(4) . . . . ? O4 Cd1 O1 C13 167.0(4) 1_455 . . . ? N1 Cd1 O2 C13 -90.2(5) . . . . ? N4 Cd1 O2 C13 98.9(5) 1_544 . . . ? O1 Cd1 O2 C13 4.9(5) . . . . ? O4 Cd1 O2 C13 -174.9(5) 2_655 . . . ? O3 Cd1 O2 C13 1.3(7) 1_455 . . . ? O4 Cd1 O2 C13 -158.6(6) 1_455 . . . ? C5 N1 C1 C2 2.8(13) . . . . ? Cd1 N1 C1 C2 -173.4(7) . . . . ? N1 C1 C2 C3 -1.9(14) . . . . ? C1 C2 C3 C4 -0.1(13) . . . . ? C1 C2 C3 C6 -178.9(8) . . . . ? C2 C3 C4 C5 1.0(13) . . . . ? C6 C3 C4 C5 179.8(8) . . . . ? C1 N1 C5 C4 -1.8(13) . . . . ? Cd1 N1 C5 C4 174.6(7) . . . . ? C3 C4 C5 N1 0.0(14) . . . . ? N3 N2 C6 C3 178.2(8) . . . . ? N3 N2 C6 S1 -0.6(12) . . . . ? C4 C3 C6 N2 -4.2(13) . . . . ? C2 C3 C6 N2 174.6(9) . . . . ? C4 C3 C6 S1 174.4(7) . . . . ? C2 C3 C6 S1 -6.8(12) . . . . ? C7 S1 C6 N2 0.6(8) . . . . ? C7 S1 C6 C3 -178.1(8) . . . . ? N2 N3 C7 C8 -179.7(9) . . . . ? N2 N3 C7 S1 0.2(11) . . . . ? C6 S1 C7 N3 -0.4(8) . . . . ? C6 S1 C7 C8 179.4(8) . . . . ? N3 C7 C8 C9 11.4(14) . . . . ? S1 C7 C8 C9 -168.4(8) . . . . ? N3 C7 C8 C12 -167.9(9) . . . . ? S1 C7 C8 C12 12.3(13) . . . . ? C7 C8 C9 C10 -179.6(9) . . . . ? C12 C8 C9 C10 -0.3(14) . . . . ? C11 N4 C10 C9 -3.2(15) . . . . ? Cd1 N4 C10 C9 176.4(8) 1_566 . . . ? C8 C9 C10 N4 1.7(17) . . . . ? C10 N4 C11 C12 3.5(14) . . . . ? Cd1 N4 C11 C12 -176.1(7) 1_566 . . . ? N4 C11 C12 C8 -2.3(14) . . . . ? C9 C8 C12 C11 0.6(13) . . . . ? C7 C8 C12 C11 179.9(9) . . . . ? Cd1 O2 C13 O1 -8.5(8) . . . . ? Cd1 O2 C13 C14 169.2(7) . . . . ? Cd1 O1 C13 O2 9.1(8) . . . . ? Cd1 O1 C13 C14 -168.7(6) . . . . ? O2 C13 C14 C15 -90.2(10) . . . . ? O1 C13 C14 C15 87.7(10) . . . . ? C13 C14 C15 C16 73.8(10) . . . . ? C14 C15 C16 C17 75.6(10) . . . . ? Cd1 O3 C17 O4 -1.1(9) 1_655 . . . ? Cd1 O3 C17 C16 177.7(7) 1_655 . . . ? Cd1 O4 C17 O3 -173.3(16) 2_655 . . . ? Cd1 O4 C17 O3 1.1(9) 1_655 . . . ? Cd1 O4 C17 C16 8(3) 2_655 . . . ? Cd1 O4 C17 C16 -177.7(7) 1_655 . . . ? C15 C16 C17 O3 33.6(12) . . . . ? C15 C16 C17 O4 -147.6(8) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.228 _refine_diff_density_min -1.120 _refine_diff_density_rms 0.322 data_xb2566 _database_code_depnum_ccdc_archive 'CCDC 738475' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 Cd2 N8 O10 S2' _chemical_formula_weight 969.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 31.025(5) _cell_length_b 7.5923(13) _cell_length_c 15.377(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3622.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2051 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 22.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 1.357 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8223 _exptl_absorpt_correction_T_max 0.8762 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 18892 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.24 _reflns_number_total 5721 _reflns_number_gt 3764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. During refinement of the structure, 23 restraints were applied in disordered pyridyl moieties and free water molecules such as dfix, flat, bind, eadp and isor. ; _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^)+(0.0665P)^2^+0.6372P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.43(4) _refine_ls_number_reflns 5721 _refine_ls_number_parameters 447 _refine_ls_number_restraints 23 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.004 _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 O102 O 0.2294(6) 0.133(2) 0.7172(16) 0.385(12) Uani 1 1 d D . . H12C H 0.2529 0.1370 0.7430 0.463 Uiso 1 1 d RD . . H12D H 0.2314 0.0772 0.6710 0.463 Uiso 1 1 d RD . . O101 O 0.3258(4) 0.199(2) 0.7598(9) 0.316(10) Uani 1 1 d D . . H11C H 0.3235 0.1886 0.8138 0.380 Uiso 1 1 d RD . . H11D H 0.3465 0.1394 0.7414 0.380 Uiso 1 1 d RD . . Cd1 Cd 0.431937(17) 0.21156(7) 0.44496(4) 0.03656(16) Uani 1 1 d . . . Cd2 Cd 0.429409(17) 0.74097(7) 0.50345(4) 0.03531(16) Uani 1 1 d . . . O1 O 0.42307(18) 0.3365(7) 0.3094(4) 0.0469(17) Uani 1 1 d . . . O2 O 0.4436(2) 0.5643(8) 0.3852(4) 0.0520(18) Uani 1 1 d . . . O3 O 0.4677(2) 0.9737(9) 0.2810(5) 0.077(2) Uani 1 1 d . . . O4 O 0.41928(19) 0.9370(7) 0.3858(4) 0.0409(15) Uani 1 1 d . . . O5 O 0.4382(2) 0.0193(8) 0.5657(4) 0.0485(18) Uani 1 1 d . . . O6 O 0.3853(2) 0.0134(10) 0.6620(4) 0.083(2) Uani 1 1 d . . . O7 O 0.42101(19) 0.4052(9) 0.5571(4) 0.0521(18) Uani 1 1 d . . . O8 O 0.43916(17) 0.6266(8) 0.6439(4) 0.0436(16) Uani 1 1 d . . . C1 C 0.4371(3) 0.4638(11) 0.6272(6) 0.038(2) Uani 1 1 d . . . C2 C 0.4208(3) 0.0582(11) 0.6364(6) 0.045(2) Uani 1 1 d . . . C3 C 0.4260(3) 0.4949(12) 0.3193(7) 0.048(3) Uani 1 1 d . . . C4 C 0.4348(3) 0.9082(11) 0.3113(6) 0.039(2) Uani 1 1 d . . . C5 C 0.4469(3) 0.1644(11) 0.6964(6) 0.050(2) Uani 1 1 d . . . H5A H 0.4601 0.1044 0.7419 0.060 Uiso 1 1 calc R . . C6 C 0.4540(3) 0.3450(12) 0.6923(6) 0.051(2) Uani 1 1 d . . . H6A H 0.4712 0.3940 0.7356 0.061 Uiso 1 1 calc R . . C7 C 0.4074(3) 0.6081(11) 0.2546(6) 0.062(3) Uani 1 1 d . . . H7A H 0.3923 0.5539 0.2097 0.075 Uiso 1 1 calc R . . C8 C 0.4098(3) 0.7883(12) 0.2526(6) 0.062(3) Uani 1 1 d . . . H8A H 0.3939 0.8433 0.2092 0.074 Uiso 1 1 calc R . . N1 N 0.35481(11) 0.7211(5) 0.5147(4) 0.048(2) Uani 1 1 d G . . C31 C 0.32757(16) 0.7455(6) 0.4439(3) 0.047(3) Uani 1 1 d G . . H31A H 0.3391 0.7683 0.3892 0.056 Uiso 1 1 calc R . . C32 C 0.28316(15) 0.7358(7) 0.4550(4) 0.054(3) Uani 1 1 d G . . H32A H 0.2649 0.7521 0.4076 0.065 Uiso 1 1 calc R . . C33 C 0.26600(11) 0.7017(7) 0.5367(4) 0.044(3) Uani 1 1 d G . . C34 C 0.29324(15) 0.6774(8) 0.6075(4) 0.049(3) Uani 1 1 d G . . H34A H 0.2818 0.6546 0.6622 0.059 Uiso 1 1 calc R . . C35 C 0.33764(14) 0.6871(7) 0.5965(4) 0.045(3) Uani 1 1 d G . . H35A H 0.3559 0.6708 0.6438 0.054 Uiso 1 1 calc R . . N2 N 0.50616(11) 0.2359(5) 0.4392(4) 0.0354(17) Uani 1 1 d G . . C21 C 0.53279(15) 0.2327(7) 0.5119(3) 0.055(3) Uani 1 1 d G . . H21A H 0.5209 0.2199 0.5671 0.066 Uiso 1 1 calc R . . C22 C 0.57715(14) 0.2487(7) 0.5022(4) 0.044(2) Uani 1 1 d G . . H22A H 0.5950 0.2466 0.5508 0.052 Uiso 1 1 calc R . . C23 C 0.59490(11) 0.2679(6) 0.4197(4) 0.040(3) Uani 1 1 d G . . C24 C 0.56828(15) 0.2710(8) 0.3470(4) 0.042(3) Uani 1 1 d G . . H24A H 0.5802 0.2838 0.2918 0.051 Uiso 1 1 calc R . . C25 C 0.52391(14) 0.2550(7) 0.3568(3) 0.041(2) Uani 1 1 d G . . H25A H 0.5061 0.2571 0.3081 0.049 Uiso 1 1 calc R . . N3 N 0.8548(2) 0.2826(10) 0.4396(8) 0.0403(18) Uani 0.636(11) 1 d PG . 1 C41 C 0.8370(3) 0.3369(13) 0.3612(8) 0.030(3) Uani 0.636(11) 1 d PG . 1 H41A H 0.8548 0.3698 0.3154 0.036 Uiso 0.636(11) 1 calc PR . 1 C42 C 0.7924(3) 0.3420(14) 0.3512(9) 0.037(4) Uani 0.636(11) 1 d PG . 1 H42A H 0.7805 0.3784 0.2987 0.044 Uiso 0.636(11) 1 calc PR . 1 C43 C 0.7658(2) 0.2929(13) 0.4197(10) 0.045(3) Uani 0.636(11) 1 d PG . 1 C44 C 0.7836(3) 0.2386(13) 0.4981(9) 0.028(3) Uani 0.636(11) 1 d PG . 1 H44A H 0.7658 0.2057 0.5440 0.033 Uiso 0.636(11) 1 calc PR . 1 C45 C 0.8282(3) 0.2335(12) 0.5081(8) 0.031(3) Uani 0.636(11) 1 d PG . 1 H45A H 0.8401 0.1971 0.5606 0.037 Uiso 0.636(11) 1 calc PR . 1 N3A N 0.8551(5) 0.2817(19) 0.4371(16) 0.0403(18) Uani 0.364(11) 1 d PG . 2 C41A C 0.8363(7) 0.275(2) 0.3551(15) 0.030(3) Uani 0.364(11) 1 d PG . 2 H41B H 0.8536 0.2659 0.3059 0.036 Uiso 0.364(11) 1 calc PR . 2 C42A C 0.7918(7) 0.281(3) 0.3466(16) 0.037(4) Uani 0.364(11) 1 d PG . 2 H42B H 0.7792 0.2763 0.2917 0.044 Uiso 0.364(11) 1 calc PR . 2 C43A C 0.7659(5) 0.294(2) 0.4201(19) 0.045(3) Uani 0.364(11) 1 d PG . 2 C44A C 0.7846(6) 0.301(2) 0.5021(17) 0.028(3) Uani 0.364(11) 1 d PG . 2 H44B H 0.7673 0.3099 0.5513 0.033 Uiso 0.364(11) 1 calc PR . 2 C45A C 0.8292(6) 0.295(2) 0.5107(15) 0.031(3) Uani 0.364(11) 1 d PG . 2 H45B H 0.8417 0.2995 0.5656 0.037 Uiso 0.364(11) 1 calc PR . 2 N4 N 0.00622(12) 0.7456(5) 0.5128(4) 0.0404(19) Uani 1 1 d G . . C11 C 0.02307(16) 0.7177(7) 0.5954(4) 0.050(3) Uani 1 1 d G . . H11A H 0.0047 0.7085 0.6430 0.060 Uiso 1 1 calc R . . C12 C 0.06738(17) 0.7035(7) 0.6069(4) 0.041(2) Uani 1 1 d G . . H12A H 0.0787 0.6848 0.6622 0.050 Uiso 1 1 calc R . . C13 C 0.09483(12) 0.7172(6) 0.5358(5) 0.043(3) Uani 1 1 d G . . C14 C 0.07798(16) 0.7452(6) 0.4532(4) 0.061(3) Uani 1 1 d G . . H14A H 0.0963 0.7544 0.4056 0.073 Uiso 1 1 calc R . . C15 C 0.03367(17) 0.7594(6) 0.4417(4) 0.043(3) Uani 1 1 d G . . H15A H 0.0224 0.7780 0.3864 0.051 Uiso 1 1 calc R . . N11 N 0.2016(2) 0.6215(11) 0.6229(5) 0.058(2) Uani 1 1 d D . . N12 N 0.1568(2) 0.6286(12) 0.6219(6) 0.071(3) Uani 1 1 d D . . S1 S 0.18104(7) 0.7614(3) 0.4764(2) 0.0559(10) Uani 1 1 d D . . C16 C 0.1428(2) 0.7002(10) 0.5495(6) 0.042(2) Uani 1 1 d D . . C36 C 0.2179(3) 0.6929(11) 0.5473(7) 0.051(3) Uani 1 1 d D . . N21 N 0.7015(2) 0.3592(13) 0.3345(6) 0.083(3) Uani 1 1 d DU . . N22 N 0.6579(3) 0.3549(12) 0.3356(6) 0.076(3) Uani 1 1 d DU . . S2 S 0.68100(7) 0.2374(3) 0.4800(2) 0.0512(10) Uani 1 1 d D . . C26 C 0.6411(3) 0.2916(11) 0.4063(7) 0.046(3) Uani 1 1 d D . . C46 C 0.7184(3) 0.3026(10) 0.4055(7) 0.045(3) Uani 1 1 d 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 O102 0.39(3) 0.40(2) 0.36(2) 0.06(3) 0.18(2) 0.01(2) O101 0.279(17) 0.51(3) 0.158(13) -0.099(14) 0.128(12) 0.110(16) Cd1 0.0231(3) 0.0490(3) 0.0376(4) 0.0001(4) -0.0003(3) -0.0002(3) Cd2 0.0223(3) 0.0487(3) 0.0349(4) 0.0000(3) -0.0004(3) -0.0010(3) O1 0.051(4) 0.035(3) 0.054(4) 0.002(3) -0.003(3) -0.005(3) O2 0.064(4) 0.051(3) 0.040(4) -0.010(3) -0.023(3) 0.018(3) O3 0.051(4) 0.093(5) 0.087(5) -0.010(5) 0.017(4) -0.012(4) O4 0.051(4) 0.050(3) 0.021(4) -0.002(3) -0.004(3) 0.002(3) O5 0.067(4) 0.041(3) 0.038(4) -0.004(3) 0.005(3) 0.000(3) O6 0.058(4) 0.106(6) 0.086(6) -0.017(4) 0.019(4) -0.031(4) O7 0.048(4) 0.067(4) 0.041(4) -0.010(3) -0.021(3) 0.018(3) O8 0.038(3) 0.050(4) 0.043(4) 0.009(3) -0.006(3) 0.000(3) C1 0.033(5) 0.041(5) 0.039(6) 0.005(4) 0.006(4) 0.003(4) C2 0.052(6) 0.044(5) 0.039(6) 0.001(4) -0.006(5) -0.006(4) C3 0.044(6) 0.051(6) 0.049(7) -0.004(6) 0.005(5) 0.011(5) C4 0.033(5) 0.050(5) 0.035(6) 0.006(4) 0.001(4) 0.010(4) C5 0.055(6) 0.051(5) 0.044(6) 0.003(5) -0.009(5) 0.003(4) C6 0.039(5) 0.075(6) 0.039(6) 0.002(5) -0.003(4) 0.005(5) C7 0.093(8) 0.046(5) 0.048(7) -0.007(5) -0.021(6) 0.000(5) C8 0.090(8) 0.066(6) 0.028(6) -0.006(5) -0.018(5) 0.006(6) N1 0.028(4) 0.044(4) 0.071(7) 0.003(4) 0.011(5) 0.000(3) C31 0.026(4) 0.072(6) 0.042(7) 0.009(8) -0.001(6) 0.006(4) C32 0.046(6) 0.074(6) 0.042(7) 0.002(6) -0.010(6) 0.005(4) C33 0.031(5) 0.061(5) 0.040(6) 0.000(4) -0.003(5) -0.001(4) C34 0.028(5) 0.083(7) 0.035(6) 0.000(5) 0.002(4) -0.011(5) C35 0.023(5) 0.062(6) 0.049(7) 0.007(5) 0.004(4) -0.001(4) N2 0.018(3) 0.055(4) 0.032(5) 0.006(5) -0.013(4) -0.004(2) C21 0.039(5) 0.075(5) 0.051(8) -0.002(6) -0.026(6) -0.011(5) C22 0.029(4) 0.083(5) 0.019(4) 0.004(5) -0.008(5) -0.010(4) C23 0.019(4) 0.060(5) 0.042(7) 0.006(4) 0.004(4) -0.003(4) C24 0.029(5) 0.062(6) 0.036(6) 0.008(5) 0.006(4) -0.001(4) C25 0.030(5) 0.068(6) 0.024(6) 0.008(5) -0.009(4) 0.001(4) N3 0.023(3) 0.069(4) 0.029(5) 0.003(4) -0.008(4) -0.003(3) C41 0.026(5) 0.028(9) 0.035(7) 0.001(6) -0.001(5) -0.003(6) C42 0.027(5) 0.039(10) 0.044(7) -0.002(7) -0.016(5) -0.005(6) C43 0.021(4) 0.058(5) 0.055(8) -0.006(5) 0.005(4) 0.000(4) C44 0.026(5) 0.018(7) 0.039(6) -0.006(7) -0.007(6) -0.007(5) C45 0.031(4) 0.013(7) 0.048(7) 0.000(7) 0.001(7) -0.005(5) N3A 0.023(3) 0.069(4) 0.029(5) 0.003(4) -0.008(4) -0.003(3) C41A 0.026(5) 0.028(9) 0.035(7) 0.001(6) -0.001(5) -0.003(6) C42A 0.027(5) 0.039(10) 0.044(7) -0.002(7) -0.016(5) -0.005(6) C43A 0.021(4) 0.058(5) 0.055(8) -0.006(5) 0.005(4) 0.000(4) C44A 0.026(5) 0.018(7) 0.039(6) -0.006(7) -0.007(6) -0.007(5) C45A 0.031(4) 0.013(7) 0.048(7) 0.000(7) 0.001(7) -0.005(5) N4 0.030(4) 0.053(3) 0.038(5) -0.001(3) -0.005(5) -0.002(3) C11 0.034(5) 0.057(6) 0.058(8) 0.014(5) 0.000(5) 0.003(4) C12 0.025(5) 0.060(5) 0.039(6) 0.009(4) 0.007(4) 0.003(4) C13 0.033(5) 0.041(5) 0.056(8) 0.008(4) -0.011(5) -0.004(4) C14 0.034(5) 0.074(7) 0.076(10) 0.023(8) -0.005(7) -0.007(4) C15 0.031(5) 0.061(5) 0.036(6) 0.003(7) -0.018(5) -0.005(3) N11 0.024(4) 0.105(6) 0.044(5) 0.014(5) 0.000(4) -0.002(4) N12 0.016(4) 0.126(7) 0.071(6) 0.025(6) -0.010(4) -0.011(4) S1 0.0242(12) 0.0810(15) 0.063(3) 0.0194(13) 0.0003(10) -0.0016(10) C16 0.016(4) 0.066(5) 0.045(7) 0.009(5) 0.004(4) 0.001(4) C36 0.024(5) 0.062(5) 0.068(8) -0.019(5) 0.015(5) -0.001(4) N21 0.016(4) 0.158(8) 0.076(7) 0.011(7) 0.005(5) -0.016(5) N22 0.035(5) 0.148(8) 0.046(6) 0.015(6) 0.001(4) -0.012(5) S2 0.0264(13) 0.0800(14) 0.047(3) 0.0172(13) -0.0032(10) -0.0008(10) C26 0.036(5) 0.068(6) 0.034(6) 0.005(5) -0.006(4) -0.006(4) C46 0.031(5) 0.051(5) 0.054(7) 0.010(5) -0.015(5) -0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O102 O101 3.11(2) . ? O102 H12C 0.8324 . ? O102 H12D 0.8274 . ? O101 O6 2.764(13) . ? O101 H11C 0.8371 . ? O101 H11D 0.8332 . ? Cd1 O7 2.292(7) . ? Cd1 O1 2.307(6) . ? Cd1 O4 2.308(6) 1_545 ? Cd1 N2 2.312(3) . ? Cd1 O5 2.370(6) . ? Cd1 N3A 2.389(15) 3_455 ? Cd1 N3 2.395(7) 3_455 ? Cd2 O2 2.301(6) . ? Cd2 N1 2.326(4) . ? Cd2 O5 2.336(6) 1_565 ? Cd2 O8 2.348(6) . ? Cd2 O4 2.363(6) . ? Cd2 N4 2.390(4) 3_565 ? O1 C3 1.215(10) . ? O2 C3 1.265(11) . ? O3 C4 1.229(10) . ? O4 C4 1.262(11) . ? O4 Cd1 2.308(6) 1_565 ? O5 C2 1.248(11) . ? O5 Cd2 2.336(6) 1_545 ? O6 C2 1.219(10) . ? O7 C1 1.268(11) . ? O8 C1 1.264(10) . ? C1 C6 1.446(12) . ? C2 C5 1.469(12) . ? C3 C7 1.437(13) . ? C4 C8 1.498(12) . ? C5 C6 1.391(12) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.371(12) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? N1 C31 1.3900 . ? N1 C35 1.3900 . ? C31 C32 1.3900 . ? C31 H31A 0.9300 . ? C32 C33 1.3900 . ? C32 H32A 0.9300 . ? C33 C34 1.3900 . ? C33 C36 1.501(9) . ? C34 C35 1.3900 . ? C34 H34A 0.9300 . ? C35 H35A 0.9300 . ? N2 C21 1.3900 . ? N2 C25 1.3900 . ? C21 C22 1.3900 . ? C21 H21A 0.9300 . ? C22 C23 1.3900 . ? C22 H22A 0.9300 . ? C23 C24 1.3900 . ? C23 C26 1.460(10) . ? C24 C25 1.3900 . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? N3 C41 1.3900 . ? N3 C45 1.3900 . ? N3 Cd1 2.395(7) 3 ? C41 C42 1.3900 . ? C41 H41A 0.9300 . ? C42 C43 1.3900 . ? C42 H42A 0.9300 . ? C43 C44 1.3900 . ? C43 C46 1.489(11) . ? C44 C45 1.3900 . ? C44 H44A 0.9300 . ? C45 H45A 0.9300 . ? N3A C41A 1.3900 . ? N3A C45A 1.3900 . ? N3A Cd1 2.389(15) 3 ? C41A C42A 1.3900 . ? C41A H41B 0.9300 . ? C42A C43A 1.3900 . ? C42A H42B 0.9300 . ? C43A C44A 1.3900 . ? C43A C46 1.493(18) . ? C44A C45A 1.3900 . ? C44A H44B 0.9300 . ? C45A H45B 0.9300 . ? N4 C11 1.3900 . ? N4 C15 1.3900 . ? N4 Cd2 2.390(4) 3_465 ? C11 C12 1.3900 . ? C11 H11A 0.9300 . ? C12 C13 1.3900 . ? C12 H12A 0.9300 . ? C13 C14 1.3900 . ? C13 C16 1.507(8) . ? C14 C15 1.3900 . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? N11 C36 1.379(13) . ? N11 N12 1.390(10) . ? N12 C16 1.314(12) . ? S1 C36 1.665(11) . ? S1 C16 1.700(9) . ? N21 C46 1.285(12) . ? N21 N22 1.354(11) . ? N22 C26 1.298(12) . ? S2 C46 1.704(10) . ? S2 C26 1.727(10) . ? 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 O101 O102 H12C 17.6 . . ? O101 O102 H12D 100.8 . . ? H12C O102 H12D 111.2 . . ? O6 O101 O102 116.5(7) . . ? O6 O101 H11C 123.4 . . ? O102 O101 H11C 96.4 . . ? O6 O101 H11D 13.3 . . ? O102 O101 H11D 125.6 . . ? H11C O101 H11D 110.7 . . ? O7 Cd1 O1 113.5(2) . . ? O7 Cd1 O4 148.3(2) . 1_545 ? O1 Cd1 O4 89.7(2) . 1_545 ? O7 Cd1 N2 97.2(2) . . ? O1 Cd1 N2 92.95(19) . . ? O4 Cd1 N2 103.10(18) 1_545 . ? O7 Cd1 O5 79.5(2) . . ? O1 Cd1 O5 166.2(2) . . ? O4 Cd1 O5 76.48(19) 1_545 . ? N2 Cd1 O5 89.87(19) . . ? O7 Cd1 N3A 82.9(5) . 3_455 ? O1 Cd1 N3A 80.0(6) . 3_455 ? O4 Cd1 N3A 80.2(4) 1_545 3_455 ? N2 Cd1 N3A 172.3(5) . 3_455 ? O5 Cd1 N3A 97.7(5) . 3_455 ? O7 Cd1 N3 82.3(3) . 3_455 ? O1 Cd1 N3 80.9(3) . 3_455 ? O4 Cd1 N3 80.4(3) 1_545 3_455 ? N2 Cd1 N3 173.0(2) . 3_455 ? O5 Cd1 N3 96.9(3) . 3_455 ? N3A Cd1 N3 0.9(8) 3_455 3_455 ? O2 Cd2 N1 102.2(2) . . ? O2 Cd2 O5 146.0(2) . 1_565 ? N1 Cd2 O5 98.28(19) . 1_565 ? O2 Cd2 O8 119.1(2) . . ? N1 Cd2 O8 92.06(19) . . ? O5 Cd2 O8 86.7(2) 1_565 . ? O2 Cd2 O4 77.8(2) . . ? N1 Cd2 O4 88.0(2) . . ? O5 Cd2 O4 76.1(2) 1_565 . ? O8 Cd2 O4 162.60(19) . . ? O2 Cd2 N4 83.2(2) . 3_565 ? N1 Cd2 N4 172.2(2) . 3_565 ? O5 Cd2 N4 79.66(19) 1_565 3_565 ? O8 Cd2 N4 80.31(19) . 3_565 ? O4 Cd2 N4 98.7(2) . 3_565 ? C3 O1 Cd1 106.5(6) . . ? C3 O2 Cd2 142.5(6) . . ? C4 O4 Cd1 116.7(5) . 1_565 ? C4 O4 Cd2 122.4(5) . . ? Cd1 O4 Cd2 104.2(2) 1_565 . ? C2 O5 Cd2 121.3(6) . 1_545 ? C2 O5 Cd1 120.1(6) . . ? Cd2 O5 Cd1 103.1(3) 1_545 . ? C2 O6 O101 129.6(7) . . ? C1 O7 Cd1 143.7(5) . . ? C1 O8 Cd2 99.6(6) . . ? O8 C1 O7 122.4(8) . . ? O8 C1 C6 116.8(8) . . ? O7 C1 C6 120.8(8) . . ? O6 C2 O5 127.3(9) . . ? O6 C2 C5 116.7(9) . . ? O5 C2 C5 116.0(8) . . ? O1 C3 O2 123.0(9) . . ? O1 C3 C7 118.3(9) . . ? O2 C3 C7 118.6(8) . . ? O3 C4 O4 126.2(9) . . ? O3 C4 C8 116.6(9) . . ? O4 C4 C8 117.1(8) . . ? C6 C5 C2 127.0(8) . . ? C6 C5 H5A 116.5 . . ? C2 C5 H5A 116.5 . . ? C5 C6 C1 126.0(8) . . ? C5 C6 H6A 117.0 . . ? C1 C6 H6A 117.0 . . ? C8 C7 C3 126.2(9) . . ? C8 C7 H7A 116.9 . . ? C3 C7 H7A 116.9 . . ? C7 C8 C4 128.4(9) . . ? C7 C8 H8A 115.8 . . ? C4 C8 H8A 115.8 . . ? C31 N1 C35 120.0 . . ? C31 N1 Cd2 122.6(3) . . ? C35 N1 Cd2 117.4(3) . . ? N1 C31 C32 120.0 . . ? N1 C31 H31A 120.0 . . ? C32 C31 H31A 120.0 . . ? C33 C32 C31 120.0 . . ? C33 C32 H32A 120.0 . . ? C31 C32 H32A 120.0 . . ? C34 C33 C32 120.0 . . ? C34 C33 C36 120.9(6) . . ? C32 C33 C36 119.1(6) . . ? C33 C34 C35 120.0 . . ? C33 C34 H34A 120.0 . . ? C35 C34 H34A 120.0 . . ? C34 C35 N1 120.0 . . ? C34 C35 H35A 120.0 . . ? N1 C35 H35A 120.0 . . ? C21 N2 C25 120.0 . . ? C21 N2 Cd1 124.0(2) . . ? C25 N2 Cd1 116.0(2) . . ? C22 C21 N2 120.0 . . ? C22 C21 H21A 120.0 . . ? N2 C21 H21A 120.0 . . ? C21 C22 C23 120.0 . . ? C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? C24 C23 C22 120.0 . . ? C24 C23 C26 117.9(5) . . ? C22 C23 C26 122.0(5) . . ? C25 C24 C23 120.0 . . ? C25 C24 H24A 120.0 . . ? C23 C24 H24A 120.0 . . ? C24 C25 N2 120.0 . . ? C24 C25 H25A 120.0 . . ? N2 C25 H25A 120.0 . . ? C41 N3 C45 120.0 . . ? C41 N3 Cd1 115.0(5) . 3 ? C45 N3 Cd1 125.0(5) . 3 ? N3 C41 C42 120.0 . . ? N3 C41 H41A 120.0 . . ? C42 C41 H41A 120.0 . . ? C41 C42 C43 120.0 . . ? C41 C42 H42A 120.0 . . ? C43 C42 H42A 120.0 . . ? C44 C43 C42 120.0 . . ? C44 C43 C46 122.4(9) . . ? C42 C43 C46 117.6(9) . . ? C45 C44 C43 120.0 . . ? C45 C44 H44A 120.0 . . ? C43 C44 H44A 120.0 . . ? C44 C45 N3 120.0 . . ? C44 C45 H45A 120.0 . . ? N3 C45 H45A 120.0 . . ? C41A N3A C45A 120.0 . . ? C41A N3A Cd1 117.6(10) . 3 ? C45A N3A Cd1 122.3(10) . 3 ? C42A C41A N3A 120.0 . . ? C42A C41A H41B 120.0 . . ? N3A C41A H41B 120.0 . . ? C43A C42A C41A 120.0 . . ? C43A C42A H42B 120.0 . . ? C41A C42A H42B 120.0 . . ? C42A C43A C44A 120.0 . . ? C42A C43A C46 116.8(17) . . ? C44A C43A C46 123.2(16) . . ? C43A C44A C45A 120.0 . . ? C43A C44A H44B 120.0 . . ? C45A C44A H44B 120.0 . . ? C44A C45A N3A 120.0 . . ? C44A C45A H45B 120.0 . . ? N3A C45A H45B 120.0 . . ? C11 N4 C15 120.0 . . ? C11 N4 Cd2 115.9(3) . 3_465 ? C15 N4 Cd2 124.1(3) . 3_465 ? N4 C11 C12 120.0 . . ? N4 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 C16 120.8(5) . . ? C12 C13 C16 119.2(5) . . ? C13 C14 C15 120.0 . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C14 C15 N4 120.0 . . ? C14 C15 H15A 120.0 . . ? N4 C15 H15A 120.0 . . ? C36 N11 N12 110.0(7) . . ? C16 N12 N11 111.0(7) . . ? C36 S1 C16 87.8(5) . . ? N12 C16 C13 118.8(8) . . ? N12 C16 S1 116.2(6) . . ? C13 C16 S1 125.0(7) . . ? N11 C36 C33 118.3(8) . . ? N11 C36 S1 115.0(6) . . ? C33 C36 S1 126.7(8) . . ? C46 N21 N22 112.9(8) . . ? C26 N22 N21 114.8(8) . . ? C46 S2 C26 88.7(5) . . ? N22 C26 C23 123.8(8) . . ? N22 C26 S2 110.6(7) . . ? C23 C26 S2 125.6(7) . . ? N21 C46 C43 123.0(10) . . ? N21 C46 C43A 123.1(14) . . ? C43 C46 C43A 0.4(12) . . ? N21 C46 S2 113.0(7) . . ? C43 C46 S2 124.0(9) . . ? C43A C46 S2 123.9(13) . . ? 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 O7 Cd1 O1 C3 19.0(6) . . . . ? O4 Cd1 O1 C3 176.8(6) 1_545 . . . ? N2 Cd1 O1 C3 -80.1(6) . . . . ? O5 Cd1 O1 C3 178.3(8) . . . . ? N3A Cd1 O1 C3 96.7(7) 3_455 . . . ? N3 Cd1 O1 C3 96.4(6) 3_455 . . . ? N1 Cd2 O2 C3 19.0(10) . . . . ? O5 Cd2 O2 C3 -106.6(10) 1_565 . . . ? O8 Cd2 O2 C3 118.3(10) . . . . ? O4 Cd2 O2 C3 -66.2(10) . . . . ? N4 Cd2 O2 C3 -166.8(10) 3_565 . . . ? O2 Cd2 O4 C4 -19.6(6) . . . . ? N1 Cd2 O4 C4 -122.5(7) . . . . ? O5 Cd2 O4 C4 138.5(7) 1_565 . . . ? O8 Cd2 O4 C4 146.9(7) . . . . ? N4 Cd2 O4 C4 61.5(7) 3_565 . . . ? O2 Cd2 O4 Cd1 -154.8(3) . . . 1_565 ? N1 Cd2 O4 Cd1 102.3(2) . . . 1_565 ? O5 Cd2 O4 Cd1 3.3(2) 1_565 . . 1_565 ? O8 Cd2 O4 Cd1 11.8(8) . . . 1_565 ? N4 Cd2 O4 Cd1 -73.7(2) 3_565 . . 1_565 ? O7 Cd1 O5 C2 23.7(7) . . . . ? O1 Cd1 O5 C2 -137.0(9) . . . . ? O4 Cd1 O5 C2 -135.5(7) 1_545 . . . ? N2 Cd1 O5 C2 121.0(7) . . . . ? N3A Cd1 O5 C2 -57.5(8) 3_455 . . . ? N3 Cd1 O5 C2 -57.1(7) 3_455 . . . ? O7 Cd1 O5 Cd2 162.5(3) . . . 1_545 ? O1 Cd1 O5 Cd2 1.7(10) . . . 1_545 ? O4 Cd1 O5 Cd2 3.3(2) 1_545 . . 1_545 ? N2 Cd1 O5 Cd2 -100.2(2) . . . 1_545 ? N3A Cd1 O5 Cd2 81.2(5) 3_455 . . 1_545 ? N3 Cd1 O5 Cd2 81.6(3) 3_455 . . 1_545 ? O102 O101 O6 C2 144.9(9) . . . . ? O1 Cd1 O7 C1 -130.0(10) . . . . ? O4 Cd1 O7 C1 96.1(10) 1_545 . . . ? N2 Cd1 O7 C1 -33.6(11) . . . . ? O5 Cd1 O7 C1 54.9(10) . . . . ? N3A Cd1 O7 C1 154.2(11) 3_455 . . . ? N3 Cd1 O7 C1 153.5(11) 3_455 . . . ? O2 Cd2 O8 C1 -21.2(5) . . . . ? N1 Cd2 O8 C1 83.9(5) . . . . ? O5 Cd2 O8 C1 -177.9(5) 1_565 . . . ? O4 Cd2 O8 C1 173.9(6) . . . . ? N4 Cd2 O8 C1 -97.8(5) 3_565 . . . ? Cd2 O8 C1 O7 -17.8(9) . . . . ? Cd2 O8 C1 C6 162.5(6) . . . . ? Cd1 O7 C1 O8 133.1(8) . . . . ? Cd1 O7 C1 C6 -47.3(14) . . . . ? O101 O6 C2 O5 -144.0(9) . . . . ? O101 O6 C2 C5 38.4(13) . . . . ? Cd2 O5 C2 O6 -37.3(13) 1_545 . . . ? Cd1 O5 C2 O6 93.9(11) . . . . ? Cd2 O5 C2 C5 140.3(6) 1_545 . . . ? Cd1 O5 C2 C5 -88.5(9) . . . . ? Cd1 O1 C3 O2 19.2(11) . . . . ? Cd1 O1 C3 C7 -158.5(7) . . . . ? Cd2 O2 C3 O1 -116.6(10) . . . . ? Cd2 O2 C3 C7 61.1(14) . . . . ? Cd1 O4 C4 O3 30.1(11) 1_565 . . . ? Cd2 O4 C4 O3 -100.0(10) . . . . ? Cd1 O4 C4 C8 -147.3(6) 1_565 . . . ? Cd2 O4 C4 C8 82.6(9) . . . . ? O6 C2 C5 C6 -103.2(11) . . . . ? O5 C2 C5 C6 78.9(12) . . . . ? C2 C5 C6 C1 -0.5(15) . . . . ? O8 C1 C6 C5 165.3(8) . . . . ? O7 C1 C6 C5 -14.4(14) . . . . ? O1 C3 C7 C8 -176.0(10) . . . . ? O2 C3 C7 C8 6.1(16) . . . . ? C3 C7 C8 C4 5.6(18) . . . . ? O3 C4 C8 C7 104.8(13) . . . . ? O4 C4 C8 C7 -77.5(14) . . . . ? O2 Cd2 N1 C31 -49.2(3) . . . . ? O5 Cd2 N1 C31 103.4(3) 1_565 . . . ? O8 Cd2 N1 C31 -169.6(3) . . . . ? O4 Cd2 N1 C31 27.8(3) . . . . ? N4 Cd2 N1 C31 177.6(9) 3_565 . . . ? O2 Cd2 N1 C35 132.2(3) . . . . ? O5 Cd2 N1 C35 -75.2(3) 1_565 . . . ? O8 Cd2 N1 C35 11.8(3) . . . . ? O4 Cd2 N1 C35 -150.8(3) . . . . ? N4 Cd2 N1 C35 -1.0(11) 3_565 . . . ? C35 N1 C31 C32 0.0 . . . . ? Cd2 N1 C31 C32 -178.6(2) . . . . ? N1 C31 C32 C33 0.0 . . . . ? C31 C32 C33 C34 0.0 . . . . ? C31 C32 C33 C36 179.6(5) . . . . ? C32 C33 C34 C35 0.0 . . . . ? C36 C33 C34 C35 -179.6(5) . . . . ? C33 C34 C35 N1 0.0 . . . . ? C31 N1 C35 C34 0.0 . . . . ? Cd2 N1 C35 C34 178.7(2) . . . . ? O7 Cd1 N2 C21 45.5(3) . . . . ? O1 Cd1 N2 C21 159.6(3) . . . . ? O4 Cd1 N2 C21 -110.0(3) 1_545 . . . ? O5 Cd1 N2 C21 -33.9(3) . . . . ? N3A Cd1 N2 C21 135(4) 3_455 . . . ? N3 Cd1 N2 C21 131(2) 3_455 . . . ? O7 Cd1 N2 C25 -134.3(3) . . . . ? O1 Cd1 N2 C25 -20.2(3) . . . . ? O4 Cd1 N2 C25 70.2(3) 1_545 . . . ? O5 Cd1 N2 C25 146.3(3) . . . . ? N3A Cd1 N2 C25 -44(4) 3_455 . . . ? N3 Cd1 N2 C25 -49(2) 3_455 . . . ? C25 N2 C21 C22 0.0 . . . . ? Cd1 N2 C21 C22 -179.8(2) . . . . ? N2 C21 C22 C23 0.0 . . . . ? C21 C22 C23 C24 0.0 . . . . ? C21 C22 C23 C26 177.7(5) . . . . ? C22 C23 C24 C25 0.0 . . . . ? C26 C23 C24 C25 -177.8(5) . . . . ? C23 C24 C25 N2 0.0 . . . . ? C21 N2 C25 C24 0.0 . . . . ? Cd1 N2 C25 C24 179.9(2) . . . . ? C45 N3 C41 C42 0.0 . . . . ? Cd1 N3 C41 C42 -178.8(4) 3 . . . ? N3 C41 C42 C43 0.0 . . . . ? C41 C42 C43 C44 0.0 . . . . ? C41 C42 C43 C46 179.5(7) . . . . ? C42 C43 C44 C45 0.0 . . . . ? C46 C43 C44 C45 -179.4(8) . . . . ? C43 C44 C45 N3 0.0 . . . . ? C41 N3 C45 C44 0.0 . . . . ? Cd1 N3 C45 C44 178.7(5) 3 . . . ? C45A N3A C41A C42A 0.0 . . . . ? Cd1 N3A C41A C42A -176.2(9) 3 . . . ? N3A C41A C42A C43A 0.0 . . . . ? C41A C42A C43A C44A 0.0 . . . . ? C41A C42A C43A C46 179.2(13) . . . . ? C42A C43A C44A C45A 0.0 . . . . ? C46 C43A C44A C45A -179.1(14) . . . . ? C43A C44A C45A N3A 0.0 . . . . ? C41A N3A C45A C44A 0.0 . . . . ? Cd1 N3A C45A C44A 176.0(9) 3 . . . ? C15 N4 C11 C12 0.0 . . . . ? Cd2 N4 C11 C12 178.4(2) 3_465 . . . ? N4 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C11 C12 C13 C16 -179.6(5) . . . . ? C12 C13 C14 C15 0.0 . . . . ? C16 C13 C14 C15 179.6(5) . . . . ? C13 C14 C15 N4 0.0 . . . . ? C11 N4 C15 C14 0.0 . . . . ? Cd2 N4 C15 C14 -178.2(2) 3_465 . . . ? C36 N11 N12 C16 0.2(9) . . . . ? N11 N12 C16 C13 179.2(7) . . . . ? N11 N12 C16 S1 1.1(9) . . . . ? C14 C13 C16 N12 -162.0(6) . . . . ? C12 C13 C16 N12 17.6(9) . . . . ? C14 C13 C16 S1 16.0(8) . . . . ? C12 C13 C16 S1 -164.5(5) . . . . ? C36 S1 C16 N12 -1.6(7) . . . . ? C36 S1 C16 C13 -179.6(7) . . . . ? N12 N11 C36 C33 178.5(7) . . . . ? N12 N11 C36 S1 -1.4(8) . . . . ? C34 C33 C36 N11 -14.5(8) . . . . ? C32 C33 C36 N11 165.8(6) . . . . ? C34 C33 C36 S1 165.4(5) . . . . ? C32 C33 C36 S1 -14.2(8) . . . . ? C16 S1 C36 N11 1.7(7) . . . . ? C16 S1 C36 C33 -178.3(7) . . . . ? C46 N21 N22 C26 -1.4(10) . . . . ? N21 N22 C26 C23 -177.2(7) . . . . ? N21 N22 C26 S2 1.8(9) . . . . ? C24 C23 C26 N22 16.5(10) . . . . ? C22 C23 C26 N22 -161.2(7) . . . . ? C24 C23 C26 S2 -162.3(5) . . . . ? C22 C23 C26 S2 20.0(8) . . . . ? C46 S2 C26 N22 -1.3(7) . . . . ? C46 S2 C26 C23 177.7(7) . . . . ? N22 N21 C46 C43 179.4(8) . . . . ? N22 N21 C46 C43A 179.9(11) . . . . ? N22 N21 C46 S2 0.4(9) . . . . ? C44 C43 C46 N21 177.2(7) . . . . ? C42 C43 C46 N21 -2.3(11) . . . . ? C44 C43 C46 C43A 79(100) . . . . ? C42 C43 C46 C43A -101(100) . . . . ? C44 C43 C46 S2 -3.9(10) . . . . ? C42 C43 C46 S2 176.6(5) . . . . ? C42A C43A C46 N21 -25.2(14) . . . . ? C44A C43A C46 N21 154.0(11) . . . . ? C42A C43A C46 C43 57(100) . . . . ? C44A C43A C46 C43 -124(100) . . . . ? C42A C43A C46 S2 154.3(8) . . . . ? C44A C43A C46 S2 -26.5(16) . . . . ? C26 S2 C46 N21 0.5(7) . . . . ? C26 S2 C46 C43 -178.5(8) . . . . ? C26 S2 C46 C43A -179.0(11) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.24 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.248 _refine_diff_density_min -0.756 _refine_diff_density_rms 0.115 # Attachment '10.cif' data_xb2285m _database_code_depnum_ccdc_archive 'CCDC 738476' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cd N4 O6 S' _chemical_formula_weight 502.77 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' Cd Cd -0.8075 1.2024 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1079(15) _cell_length_b 7.6454(15) _cell_length_c 16.848(3) _cell_angle_alpha 79.895(3) _cell_angle_beta 85.666(4) _cell_angle_gamma 85.100(4) _cell_volume 896.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.863 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 1.379 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7377 _exptl_absorpt_correction_T_max 0.8643 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4542 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0886 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.20 _reflns_number_total 3152 _reflns_number_gt 2230 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. During refinement of the structure, 6 restraints were applied including thermal restraints (isor, delu and simu) which have been used in disordered C1 atom. ; _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^)+(0.0883P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3152 _refine_ls_number_parameters 253 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.047 _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 Cd1 Cd 0.65415(9) 0.01166(7) 0.58860(3) 0.0294(2) Uani 1 1 d . . . S1 S -0.0542(3) 0.2531(3) 0.92811(13) 0.0474(6) Uani 1 1 d . . . N1 N 0.4831(10) 0.0740(8) 0.7030(4) 0.0351(17) Uani 1 1 d . . . N2 N 0.2592(12) 0.1756(13) 0.9860(5) 0.061(2) Uani 1 1 d . . . N3 N 0.1499(12) 0.2113(13) 1.0489(5) 0.060(2) Uani 1 1 d . . . N4 N -0.4647(13) 0.4017(10) 1.1944(5) 0.052(2) Uani 1 1 d . . . O1 O 0.8396(10) 0.2476(9) 0.6256(5) 0.0569(18) Uani 1 1 d . . . O2 O 0.8583(8) 0.1902(8) 0.5015(4) 0.0471(16) Uani 1 1 d . . . O3 O 0.5209(9) -0.2607(7) 0.6166(3) 0.0436(16) Uani 1 1 d . . . O4 O 0.5887(8) -0.1790(7) 0.4856(3) 0.0353(14) Uani 1 1 d . . . O5 O 0.9170(9) -0.1613(8) 0.6406(4) 0.0488(16) Uani 1 1 d . . . O6 O 0.8260(9) 0.5054(8) 0.7273(4) 0.0526(17) Uani 1 1 d . . . H5B H 0.8762 -0.2527 0.6676 0.063 Uiso 1 1 d R . . H5A H 0.9924 -0.1821 0.6037 0.063 Uiso 1 1 d R . . H6A H 0.7594 0.4685 0.6966 0.063 Uiso 1 1 d R . . H6B H 0.7550 0.5498 0.7604 0.063 Uiso 1 1 d R . . C1 C 0.5621(12) 0.0656(12) 0.7723(5) 0.041(2) Uani 1 1 d U . . H1 H 0.6914 0.0341 0.7724 0.050 Uiso 1 1 calc R . . C2 C 0.4744(14) 0.0981(13) 0.8432(5) 0.050(3) Uani 1 1 d . . . H2 H 0.5405 0.0851 0.8897 0.060 Uiso 1 1 calc R . . C3 C 0.2793(13) 0.1524(10) 0.8439(5) 0.037(2) Uani 1 1 d . . . C4 C 0.1959(13) 0.1630(13) 0.7727(5) 0.047(2) Uani 1 1 d . . . H4 H 0.0671 0.1962 0.7711 0.056 Uiso 1 1 calc R . . C5 C 0.2908(14) 0.1279(13) 0.7052(5) 0.049(2) Uani 1 1 d . . . H5 H 0.2266 0.1397 0.6582 0.058 Uiso 1 1 calc R . . C6 C 0.1829(12) 0.1881(11) 0.9188(5) 0.036(2) Uani 1 1 d . . . C7 C -0.0275(13) 0.2571(11) 1.0285(5) 0.037(2) Uani 1 1 d . . . C8 C -0.1805(13) 0.3059(11) 1.0854(5) 0.038(2) Uani 1 1 d . . . C9 C -0.1420(15) 0.3254(13) 1.1624(5) 0.052(3) Uani 1 1 d . . . H9 H -0.0189 0.3078 1.1790 0.062 Uiso 1 1 calc R . . C10 C -0.2922(17) 0.3721(14) 1.2147(6) 0.058(3) Uani 1 1 d . . . H10 H -0.2664 0.3824 1.2669 0.070 Uiso 1 1 calc R . . C11 C -0.5010(17) 0.3824(14) 1.1203(6) 0.061(3) Uani 1 1 d . . . H11 H -0.6257 0.4038 1.1060 0.073 Uiso 1 1 calc R . . C12 C -0.3698(12) 0.3338(14) 1.0642(6) 0.049(3) Uani 1 1 d . . . H12 H -0.4035 0.3195 1.0136 0.059 Uiso 1 1 calc R . . C13 C 0.5342(12) -0.2909(10) 0.5462(5) 0.035(2) Uani 1 1 d . . . C14 C 0.4869(12) -0.4718(10) 0.5356(5) 0.034(2) Uani 1 1 d . . . H14 H 0.4374 -0.5480 0.5800 0.041 Uiso 1 1 calc R . . C15 C 0.8955(13) 0.2831(12) 0.5544(7) 0.047(3) Uani 1 1 d . . . C16 C 1.0046(15) 0.4457(14) 0.5299(7) 0.070(4) Uani 1 1 d . . . H16 H 1.0903 0.4640 0.5662 0.084 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 Cd1 0.0367(4) 0.0233(3) 0.0292(4) -0.0057(2) 0.0014(2) -0.0080(2) S1 0.0381(15) 0.0711(17) 0.0330(13) -0.0139(12) 0.0004(10) 0.0043(13) N1 0.043(5) 0.027(3) 0.037(4) -0.008(3) -0.001(3) -0.003(3) N2 0.048(5) 0.102(7) 0.037(5) -0.031(5) -0.001(4) 0.003(5) N3 0.050(6) 0.097(7) 0.036(5) -0.032(5) -0.001(4) 0.018(5) N4 0.069(6) 0.048(5) 0.038(5) -0.007(4) 0.017(4) -0.007(4) O1 0.050(5) 0.043(4) 0.078(5) -0.013(4) 0.013(4) -0.013(3) O2 0.028(4) 0.050(4) 0.056(4) 0.008(3) 0.006(3) -0.002(3) O3 0.068(5) 0.035(3) 0.031(3) -0.009(3) -0.002(3) -0.022(3) O4 0.049(4) 0.027(3) 0.031(3) -0.004(3) 0.000(3) -0.013(3) O5 0.045(4) 0.040(3) 0.059(4) -0.005(3) 0.002(3) -0.004(3) O6 0.065(5) 0.053(4) 0.040(4) -0.009(3) -0.006(3) -0.007(3) C1 0.014(4) 0.061(5) 0.048(5) -0.016(4) -0.001(4) 0.015(4) C2 0.051(7) 0.069(7) 0.033(5) -0.020(5) -0.005(4) 0.000(5) C3 0.048(6) 0.031(4) 0.033(5) -0.003(4) -0.001(4) -0.010(4) C4 0.029(5) 0.073(7) 0.035(5) -0.012(5) 0.004(4) 0.018(5) C5 0.051(7) 0.068(6) 0.029(5) -0.010(5) -0.006(4) -0.007(5) C6 0.037(5) 0.038(5) 0.032(5) -0.012(4) 0.003(4) 0.002(4) C7 0.049(6) 0.031(4) 0.032(5) -0.008(4) -0.001(4) -0.007(4) C8 0.050(6) 0.033(5) 0.030(5) -0.009(4) 0.005(4) -0.004(4) C9 0.055(7) 0.066(7) 0.035(5) -0.015(5) 0.001(5) 0.002(5) C10 0.073(8) 0.073(7) 0.033(5) -0.015(5) 0.001(5) -0.016(6) C11 0.066(8) 0.069(7) 0.050(7) -0.013(6) 0.003(6) -0.014(6) C12 0.022(5) 0.087(8) 0.039(5) -0.024(5) 0.001(4) 0.015(5) C13 0.046(6) 0.024(4) 0.037(5) -0.006(4) -0.011(4) -0.010(4) C14 0.049(6) 0.021(4) 0.031(4) 0.000(3) -0.005(4) -0.010(4) C15 0.022(5) 0.029(5) 0.086(8) 0.000(5) -0.001(5) -0.004(4) C16 0.032(6) 0.056(7) 0.109(10) 0.018(6) 0.002(6) -0.010(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 Cd1 N1 2.299(7) . ? Cd1 O3 2.319(5) . ? Cd1 O2 2.332(6) . ? Cd1 O5 2.329(6) . ? Cd1 O4 2.360(5) 2_656 ? Cd1 O1 2.511(7) . ? Cd1 O4 2.545(5) . ? S1 C7 1.722(8) . ? S1 C6 1.720(9) . ? N1 C1 1.322(10) . ? N1 C5 1.393(11) . ? N2 C6 1.277(11) . ? N2 N3 1.319(10) . ? N3 C7 1.334(11) . ? N4 C10 1.288(12) . ? N4 C11 1.330(12) . ? O1 C15 1.227(12) . ? O2 C15 1.287(12) . ? O3 C13 1.244(10) . ? O4 C13 1.270(9) . ? O4 Cd1 2.360(5) 2_656 ? O5 H5B 0.8260 . ? O5 H5A 0.8169 . ? O6 H6A 0.8254 . ? O6 H6B 0.8218 . ? C1 C2 1.357(12) . ? C1 H1 0.9300 . ? C2 C3 1.413(12) . ? C2 H2 0.9300 . ? C3 C4 1.366(11) . ? C3 C6 1.447(12) . ? C4 C5 1.334(12) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.463(12) . ? C8 C9 1.381(12) . ? C8 C12 1.408(11) . ? C9 C10 1.395(13) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.353(13) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.495(10) . ? C14 C14 1.339(16) 2_646 ? C14 H14 0.9300 . ? C15 C16 1.501(13) . ? C16 C16 1.19(2) 2_766 ? C16 H16 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 N1 Cd1 O3 85.7(2) . . ? N1 Cd1 O2 128.5(2) . . ? O3 Cd1 O2 145.8(2) . . ? N1 Cd1 O5 102.8(2) . . ? O3 Cd1 O5 82.1(2) . . ? O2 Cd1 O5 88.8(2) . . ? N1 Cd1 O4 87.0(2) . 2_656 ? O3 Cd1 O4 98.7(2) . 2_656 ? O2 Cd1 O4 85.2(2) . 2_656 ? O5 Cd1 O4 170.3(2) . 2_656 ? N1 Cd1 O1 78.8(2) . . ? O3 Cd1 O1 152.5(2) . . ? O2 Cd1 O1 54.0(2) . . ? O5 Cd1 O1 79.4(2) . . ? O4 Cd1 O1 103.0(2) 2_656 . ? N1 Cd1 O4 131.6(2) . . ? O3 Cd1 O4 53.91(18) . . ? O2 Cd1 O4 95.1(2) . . ? O5 Cd1 O4 97.2(2) . . ? O4 Cd1 O4 75.8(2) 2_656 . ? O1 Cd1 O4 148.8(2) . . ? C7 S1 C6 88.0(4) . . ? C1 N1 C5 114.3(7) . . ? C1 N1 Cd1 122.1(6) . . ? C5 N1 Cd1 123.6(5) . . ? C6 N2 N3 117.7(8) . . ? N2 N3 C7 110.9(7) . . ? C10 N4 C11 117.9(9) . . ? C15 O1 Cd1 88.2(6) . . ? C15 O2 Cd1 95.0(6) . . ? C13 O3 Cd1 96.7(5) . . ? C13 O4 Cd1 115.7(5) . 2_656 ? C13 O4 Cd1 85.6(4) . . ? Cd1 O4 Cd1 104.2(2) 2_656 . ? Cd1 O5 H5B 106.1 . . ? Cd1 O5 H5A 110.0 . . ? H5B O5 H5A 112.6 . . ? H6A O6 H6B 107.6 . . ? N1 C1 C2 126.9(8) . . ? N1 C1 H1 116.6 . . ? C2 C1 H1 116.6 . . ? C1 C2 C3 117.7(8) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 116.1(8) . . ? C4 C3 C6 125.2(8) . . ? C2 C3 C6 118.7(7) . . ? C5 C4 C3 123.0(9) . . ? C5 C4 H4 118.5 . . ? C3 C4 H4 118.5 . . ? C4 C5 N1 122.0(8) . . ? C4 C5 H5 119.0 . . ? N1 C5 H5 119.0 . . ? N2 C6 C3 125.5(8) . . ? N2 C6 S1 111.1(7) . . ? C3 C6 S1 123.4(6) . . ? N3 C7 C8 123.4(8) . . ? N3 C7 S1 112.3(7) . . ? C8 C7 S1 124.3(7) . . ? C9 C8 C12 118.0(8) . . ? C9 C8 C7 120.3(8) . . ? C12 C8 C7 121.7(7) . . ? C8 C9 C10 118.4(9) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? N4 C10 C9 123.5(9) . . ? N4 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? N4 C11 C12 124.8(10) . . ? N4 C11 H11 117.6 . . ? C12 C11 H11 117.6 . . ? C11 C12 C8 117.4(9) . . ? C11 C12 H12 121.3 . . ? C8 C12 H12 121.3 . . ? O3 C13 O4 123.4(7) . . ? O3 C13 C14 116.2(7) . . ? O4 C13 C14 120.4(7) . . ? C14 C14 C13 122.3(10) 2_646 . ? C14 C14 H14 118.8 2_646 . ? C13 C14 H14 118.8 . . ? O1 C15 O2 122.4(9) . . ? O1 C15 C16 117.0(10) . . ? O2 C15 C16 120.6(11) . . ? C16 C16 C15 128.3(16) 2_766 . ? C16 C16 H16 115.8 2_766 . ? C15 C16 H16 115.8 . . ? 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 Cd1 N1 C1 102.5(7) . . . . ? O2 Cd1 N1 C1 -77.1(7) . . . . ? O5 Cd1 N1 C1 21.6(7) . . . . ? O4 Cd1 N1 C1 -158.6(7) 2_656 . . . ? O1 Cd1 N1 C1 -54.7(7) . . . . ? O4 Cd1 N1 C1 133.5(6) . . . . ? O3 Cd1 N1 C5 -79.3(7) . . . . ? O2 Cd1 N1 C5 101.1(7) . . . . ? O5 Cd1 N1 C5 -160.1(6) . . . . ? O4 Cd1 N1 C5 19.6(7) 2_656 . . . ? O1 Cd1 N1 C5 123.5(7) . . . . ? O4 Cd1 N1 C5 -48.3(7) . . . . ? C6 N2 N3 C7 -0.5(14) . . . . ? N1 Cd1 O1 C15 -154.8(6) . . . . ? O3 Cd1 O1 C15 148.3(6) . . . . ? O2 Cd1 O1 C15 3.5(5) . . . . ? O5 Cd1 O1 C15 99.8(6) . . . . ? O4 Cd1 O1 C15 -70.6(6) 2_656 . . . ? O4 Cd1 O1 C15 13.4(8) . . . . ? N1 Cd1 O2 C15 24.2(6) . . . . ? O3 Cd1 O2 C15 -155.1(5) . . . . ? O5 Cd1 O2 C15 -81.2(5) . . . . ? O4 Cd1 O2 C15 106.5(5) 2_656 . . . ? O1 Cd1 O2 C15 -3.4(5) . . . . ? O4 Cd1 O2 C15 -178.3(5) . . . . ? N1 Cd1 O3 C13 154.9(5) . . . . ? O2 Cd1 O3 C13 -25.7(7) . . . . ? O5 Cd1 O3 C13 -101.6(5) . . . . ? O4 Cd1 O3 C13 68.6(5) 2_656 . . . ? O1 Cd1 O3 C13 -149.7(5) . . . . ? O4 Cd1 O3 C13 3.3(5) . . . . ? N1 Cd1 O4 C13 -42.7(6) . . . . ? O3 Cd1 O4 C13 -3.2(5) . . . . ? O2 Cd1 O4 C13 160.9(5) . . . . ? O5 Cd1 O4 C13 71.5(5) . . . . ? O4 Cd1 O4 C13 -115.4(6) 2_656 . . . ? O1 Cd1 O4 C13 152.9(5) . . . . ? N1 Cd1 O4 Cd1 72.7(3) . . . 2_656 ? O3 Cd1 O4 Cd1 112.1(3) . . . 2_656 ? O2 Cd1 O4 Cd1 -83.7(2) . . . 2_656 ? O5 Cd1 O4 Cd1 -173.2(2) . . . 2_656 ? O4 Cd1 O4 Cd1 0.0 2_656 . . 2_656 ? O1 Cd1 O4 Cd1 -91.7(4) . . . 2_656 ? C5 N1 C1 C2 2.2(14) . . . . ? Cd1 N1 C1 C2 -179.4(8) . . . . ? N1 C1 C2 C3 -2.2(16) . . . . ? C1 C2 C3 C4 1.5(13) . . . . ? C1 C2 C3 C6 -179.9(9) . . . . ? C2 C3 C4 C5 -1.1(15) . . . . ? C6 C3 C4 C5 -179.7(9) . . . . ? C3 C4 C5 N1 1.3(16) . . . . ? C1 N1 C5 C4 -1.6(13) . . . . ? Cd1 N1 C5 C4 -180.0(7) . . . . ? N3 N2 C6 C3 -179.3(9) . . . . ? N3 N2 C6 S1 0.5(12) . . . . ? C4 C3 C6 N2 178.8(10) . . . . ? C2 C3 C6 N2 0.3(14) . . . . ? C4 C3 C6 S1 -1.0(13) . . . . ? C2 C3 C6 S1 -179.4(7) . . . . ? C7 S1 C6 N2 -0.2(8) . . . . ? C7 S1 C6 C3 179.5(8) . . . . ? N2 N3 C7 C8 -179.4(8) . . . . ? N2 N3 C7 S1 0.3(11) . . . . ? C6 S1 C7 N3 -0.1(7) . . . . ? C6 S1 C7 C8 179.6(8) . . . . ? N3 C7 C8 C9 7.2(14) . . . . ? S1 C7 C8 C9 -172.5(7) . . . . ? N3 C7 C8 C12 -172.7(9) . . . . ? S1 C7 C8 C12 7.6(12) . . . . ? C12 C8 C9 C10 -0.2(14) . . . . ? C7 C8 C9 C10 179.9(9) . . . . ? C11 N4 C10 C9 1.7(16) . . . . ? C8 C9 C10 N4 -1.5(16) . . . . ? C10 N4 C11 C12 -0.1(16) . . . . ? N4 C11 C12 C8 -1.5(17) . . . . ? C9 C8 C12 C11 1.6(15) . . . . ? C7 C8 C12 C11 -178.6(9) . . . . ? Cd1 O3 C13 O4 -6.5(9) . . . . ? Cd1 O3 C13 C14 171.9(6) . . . . ? Cd1 O4 C13 O3 -97.8(9) 2_656 . . . ? Cd1 O4 C13 O3 5.9(9) . . . . ? Cd1 O4 C13 C14 83.9(9) 2_656 . . . ? Cd1 O4 C13 C14 -172.5(8) . . . . ? O3 C13 C14 C14 -173.2(10) . . . 2_646 ? O4 C13 C14 C14 5.2(16) . . . 2_646 ? Cd1 O1 C15 O2 -6.1(9) . . . . ? Cd1 O1 C15 C16 171.6(7) . . . . ? Cd1 O2 C15 O1 6.6(10) . . . . ? Cd1 O2 C15 C16 -171.0(7) . . . . ? O1 C15 C16 C16 -139.7(18) . . . 2_766 ? O2 C15 C16 C16 38(2) . . . 2_766 ? 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 O6 H6B N4 0.82 2.17 2.888(11) 146.2 2_567 O6 H6A O1 0.83 2.25 2.820(9) 126.8 . O5 H5A O2 0.82 2.00 2.806(9) 167.1 2_756 O5 H5B O6 0.83 1.99 2.807(8) 169.1 1_545 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.869 _refine_diff_density_min -0.810 _refine_diff_density_rms 0.207