# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_p1b _database_code_depnum_ccdc_archive 'CCDC 896609' #TrackingRef '13293_web_deposit_cif_file_0_RobertLaDuca_1345044615.0coso43pinafinal.cif' _audit_update_record ; 2012-06-12 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H27 Co N3 O14 S' _chemical_formula_weight 516.35 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' Co Co 0.3494 0.9721 '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 7.0454(4) _cell_length_b 12.1205(7) _cell_length_c 13.2868(8) _cell_angle_alpha 70.681(1) _cell_angle_beta 86.723(1) _cell_angle_gamma 80.613(1) _cell_volume 1056.38(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4080 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 25.33 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 538 _exptl_absorpt_coefficient_mu 0.984 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6741 _exptl_absorpt_correction_T_max 0.8435 _exptl_absorpt_process_details TWINABS _exptl_special_details ? _diffrn_ambient_temperature 173(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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 31373 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3877 _reflns_number_gt 3612 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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. ; _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^)+(0.0439P)^2^+1.9229P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3877 _refine_ls_number_parameters 328 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.092 _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 Co1 Co 0.5000 0.0000 0.0000 0.01700(14) Uani 1 2 d S . . Co2 Co 0.0000 1.0000 -0.5000 0.01948(14) Uani 1 2 d S . . S1 S -0.06663(9) 0.20299(6) 0.11497(5) 0.01928(16) Uani 1 1 d . . . O1W O 0.4485(3) 1.23906(19) -0.61734(18) 0.0301(5) Uani 1 1 d D . . H1WA H 0.454(5) 1.276(3) -0.6828(15) 0.036 Uiso 1 1 d D . . H1WB H 0.416(5) 1.287(3) -0.584(2) 0.036 Uiso 1 1 d D . . O1 O -0.0406(3) 0.17951(18) 0.01252(15) 0.0266(4) Uani 1 1 d . . . O2 O -0.2098(3) 0.13417(18) 0.18034(15) 0.0267(4) Uani 1 1 d . . . O2W O -0.0126(5) 1.4228(2) -0.7467(2) 0.0485(7) Uani 1 1 d D . . H2WA H -0.050(6) 1.394(4) -0.790(3) 0.058 Uiso 1 1 d D . . H2WB H 0.056(6) 1.475(3) -0.780(3) 0.058 Uiso 1 1 d D . . O3 O -0.1317(4) 0.32946(19) 0.09462(19) 0.0387(5) Uani 1 1 d . . . O3W O 0.2222(5) 1.5904(3) -0.8457(2) 0.0584(8) Uani 1 1 d D . . H3WA H 0.301(6) 1.542(3) -0.873(3) 0.070 Uiso 1 1 d D . . H3WB H 0.192(7) 1.646(3) -0.908(2) 0.070 Uiso 1 1 d D . . O4 O 0.1177(3) 0.1676(2) 0.17189(16) 0.0311(5) Uani 1 1 d . . . O4W O 0.4846(5) 1.3774(3) -0.8290(3) 0.0696(9) Uani 1 1 d D . . H4WA H 0.394(5) 1.402(5) -0.875(3) 0.083 Uiso 1 1 d D . . H4WB H 0.593(4) 1.355(5) -0.854(4) 0.083 Uiso 1 1 d D . . O5 O 0.3413(3) 0.41566(17) -0.52708(16) 0.0305(5) Uani 1 1 d . . . O5W O 0.2315(6) 1.4210(3) -0.9952(3) 0.0884(12) Uani 1 1 d D . . H5WA H 0.179(4) 1.5026(17) -1.025(3) 0.106 Uiso 1 1 d D . . H5WB H 0.1817 1.3556 -0.9479 0.106 Uiso 1 1 d RD . . O6 O 0.2368(3) 0.93870(18) -0.39634(16) 0.0270(4) Uani 1 1 d D . . H6A H 0.220(5) 0.917(3) -0.3291(15) 0.032 Uiso 1 1 d D . . H6B H 0.326(4) 0.890(3) -0.407(3) 0.032 Uiso 1 1 d D . . O7 O 0.1778(3) 1.09525(18) -0.61577(16) 0.0275(4) Uani 1 1 d D . . H7A H 0.256(4) 1.137(3) -0.605(3) 0.033 Uiso 1 1 d D . . H7B H 0.149(5) 1.121(3) -0.6812(16) 0.033 Uiso 1 1 d D . . O8 O 0.4681(3) 0.12521(17) 0.08052(15) 0.0217(4) Uani 1 1 d D . . H8A H 0.559(3) 0.136(3) 0.112(2) 0.026 Uiso 1 1 d D . . H8B H 0.365(3) 0.140(3) 0.109(2) 0.026 Uiso 1 1 d D . . O9 O 0.2211(3) -0.02452(18) 0.03909(17) 0.0252(4) Uani 1 1 d D . . H9A H 0.171(4) -0.074(2) 0.021(3) 0.030 Uiso 1 1 d D . . H9B H 0.143(4) 0.039(2) 0.025(3) 0.030 Uiso 1 1 d D . . N1 N 0.4113(3) 0.1461(2) -0.14818(18) 0.0212(5) Uani 1 1 d . . . N2 N 0.1965(3) 0.53593(19) -0.43638(19) 0.0206(5) Uani 1 1 d . . . H2N H 0.157(5) 0.541(3) -0.377(3) 0.025 Uiso 1 1 d . . . N3 N 0.0761(3) 0.8542(2) -0.56087(18) 0.0225(5) Uani 1 1 d . . . C1 C 0.3900(5) 0.2586(3) -0.1513(2) 0.0344(7) Uani 1 1 d . . . H1 H 0.4042 0.2743 -0.0869 0.041 Uiso 1 1 calc R . . C2 C 0.3481(5) 0.3536(3) -0.2436(2) 0.0354(8) Uani 1 1 d . . . H2 H 0.3342 0.4322 -0.2416 0.043 Uiso 1 1 calc R . . C3 C 0.3268(4) 0.3341(2) -0.3383(2) 0.0198(5) Uani 1 1 d . . . C4 C 0.3519(5) 0.2181(2) -0.3362(2) 0.0286(7) Uani 1 1 d . . . H4 H 0.3408 0.2004 -0.3999 0.034 Uiso 1 1 calc R . . C5 C 0.3931(5) 0.1282(2) -0.2411(2) 0.0293(7) Uani 1 1 d . . . H5 H 0.4096 0.0490 -0.2415 0.035 Uiso 1 1 calc R . . C6 C 0.1091(4) 0.7445(2) -0.4908(2) 0.0212(6) Uani 1 1 d . . . H6 H 0.0944 0.7349 -0.4169 0.025 Uiso 1 1 calc R . . C7 C 0.1637(4) 0.6439(2) -0.5205(2) 0.0189(5) Uani 1 1 d . . . C8 C 0.1800(4) 0.6573(2) -0.6282(2) 0.0224(6) Uani 1 1 d . . . H8 H 0.2138 0.5905 -0.6515 0.027 Uiso 1 1 calc R . . C9 C 0.1457(4) 0.7708(2) -0.7009(2) 0.0245(6) Uani 1 1 d . . . H9 H 0.1568 0.7827 -0.7752 0.029 Uiso 1 1 calc R . . C10 C 0.0955(4) 0.8662(2) -0.6653(2) 0.0240(6) Uani 1 1 d . . . H10 H 0.0737 0.9434 -0.7162 0.029 Uiso 1 1 calc R . . C11 C 0.2887(4) 0.4318(2) -0.4428(2) 0.0204(5) 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 Co1 0.0155(2) 0.0158(3) 0.0183(3) -0.00365(19) -0.00348(19) -0.00121(19) Co2 0.0256(3) 0.0135(2) 0.0166(3) -0.00325(19) -0.0011(2) 0.0015(2) S1 0.0208(3) 0.0190(3) 0.0188(3) -0.0070(3) -0.0009(2) -0.0030(3) O1W 0.0346(12) 0.0270(11) 0.0312(11) -0.0154(9) 0.0003(10) 0.0005(9) O1 0.0297(11) 0.0344(11) 0.0183(10) -0.0111(9) 0.0005(8) -0.0068(9) O2 0.0278(11) 0.0337(11) 0.0189(10) -0.0059(8) -0.0008(8) -0.0113(9) O2W 0.0740(19) 0.0413(15) 0.0348(14) -0.0162(11) 0.0147(13) -0.0194(13) O3 0.0488(14) 0.0193(11) 0.0457(14) -0.0097(10) 0.0019(11) -0.0012(10) O3W 0.083(2) 0.0445(16) 0.0443(16) -0.0047(13) -0.0147(15) -0.0144(15) O4 0.0234(10) 0.0475(13) 0.0244(11) -0.0143(10) -0.0024(8) -0.0049(9) O4W 0.059(2) 0.069(2) 0.0597(19) -0.0096(16) 0.0193(15) 0.0168(16) O5 0.0492(13) 0.0181(10) 0.0197(10) -0.0056(8) 0.0002(9) 0.0065(9) O5W 0.113(3) 0.056(2) 0.089(3) -0.0133(19) 0.007(2) -0.018(2) O6 0.0286(11) 0.0289(11) 0.0194(10) -0.0068(9) -0.0020(8) 0.0054(9) O7 0.0355(12) 0.0293(11) 0.0184(10) -0.0056(8) -0.0011(9) -0.0113(9) O8 0.0180(9) 0.0245(10) 0.0241(10) -0.0103(8) -0.0039(8) -0.0010(8) O9 0.0179(10) 0.0261(11) 0.0342(11) -0.0130(9) -0.0028(8) -0.0026(8) N1 0.0220(11) 0.0177(11) 0.0213(11) -0.0029(9) -0.0041(9) -0.0017(9) N2 0.0288(12) 0.0150(11) 0.0154(11) -0.0037(9) 0.0025(9) 0.0004(9) N3 0.0284(12) 0.0145(11) 0.0213(12) -0.0034(9) -0.0005(9) 0.0012(9) C1 0.055(2) 0.0232(15) 0.0215(15) -0.0074(12) -0.0087(14) 0.0056(14) C2 0.059(2) 0.0170(14) 0.0275(16) -0.0084(12) -0.0088(15) 0.0065(14) C3 0.0188(13) 0.0173(13) 0.0213(13) -0.0042(11) -0.0024(10) -0.0012(10) C4 0.0447(18) 0.0183(14) 0.0226(14) -0.0067(11) -0.0075(13) -0.0021(12) C5 0.0456(18) 0.0147(13) 0.0263(15) -0.0038(11) -0.0090(13) -0.0042(12) C6 0.0260(14) 0.0163(13) 0.0197(13) -0.0050(10) -0.0001(11) -0.0003(11) C7 0.0191(13) 0.0146(12) 0.0203(13) -0.0030(10) -0.0005(10) -0.0009(10) C8 0.0272(14) 0.0165(13) 0.0217(14) -0.0058(11) 0.0009(11) 0.0005(11) C9 0.0308(15) 0.0220(14) 0.0173(13) -0.0038(11) 0.0007(11) -0.0006(12) C10 0.0318(15) 0.0163(13) 0.0192(13) -0.0011(11) -0.0008(11) -0.0001(11) C11 0.0231(13) 0.0142(12) 0.0230(14) -0.0050(11) -0.0023(11) -0.0020(10) _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 Co1 O9 2.0471(19) 2_655 ? Co1 O9 2.0471(19) . ? Co1 O8 2.1057(19) . ? Co1 O8 2.1057(19) 2_655 ? Co1 N1 2.208(2) 2_655 ? Co1 N1 2.208(2) . ? Co2 O7 2.084(2) 2_574 ? Co2 O7 2.084(2) . ? Co2 O6 2.101(2) 2_574 ? Co2 O6 2.101(2) . ? Co2 N3 2.157(2) . ? Co2 N3 2.157(2) 2_574 ? S1 O3 1.464(2) . ? S1 O4 1.469(2) . ? S1 O2 1.471(2) . ? S1 O1 1.476(2) . ? O1W H1WA 0.838(18) . ? O1W H1WB 0.834(18) . ? O2W H2WA 0.836(19) . ? O2W H2WB 0.851(19) . ? O3W H3WA 0.889(19) . ? O3W H3WB 0.883(19) . ? O4W H4WA 0.856(19) . ? O4W H4WB 0.854(19) . ? O5 C11 1.225(3) . ? O5W H5WA 0.954(19) . ? O5W H5WB 0.9387 . ? O6 H6A 0.850(18) . ? O6 H6B 0.829(18) . ? O7 H7A 0.848(18) . ? O7 H7B 0.844(18) . ? O8 H8A 0.833(18) . ? O8 H8B 0.821(18) . ? O9 H9A 0.849(18) . ? O9 H9B 0.840(18) . ? N1 C1 1.335(4) . ? N1 C5 1.339(4) . ? N2 C11 1.349(3) . ? N2 C7 1.407(3) . ? N2 H2N 0.83(3) . ? N3 C6 1.339(3) . ? N3 C10 1.347(4) . ? C1 C2 1.383(4) . ? C1 H1 0.9500 . ? C2 C3 1.375(4) . ? C2 H2 0.9500 . ? C3 C4 1.379(4) . ? C3 C11 1.502(4) . ? C4 C5 1.376(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.392(4) . ? C6 H6 0.9500 . ? C7 C8 1.386(4) . ? C8 C9 1.387(4) . ? C8 H8 0.9500 . ? C9 C10 1.377(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Co1 O9 180.0 2_655 . ? O9 Co1 O8 91.32(8) 2_655 . ? O9 Co1 O8 88.68(8) . . ? O9 Co1 O8 88.68(8) 2_655 2_655 ? O9 Co1 O8 91.32(8) . 2_655 ? O8 Co1 O8 180.0 . 2_655 ? O9 Co1 N1 91.99(8) 2_655 2_655 ? O9 Co1 N1 88.01(8) . 2_655 ? O8 Co1 N1 91.55(8) . 2_655 ? O8 Co1 N1 88.45(8) 2_655 2_655 ? O9 Co1 N1 88.01(8) 2_655 . ? O9 Co1 N1 91.99(8) . . ? O8 Co1 N1 88.45(8) . . ? O8 Co1 N1 91.55(8) 2_655 . ? N1 Co1 N1 180.0 2_655 . ? O7 Co2 O7 179.999(1) 2_574 . ? O7 Co2 O6 88.27(8) 2_574 2_574 ? O7 Co2 O6 91.73(8) . 2_574 ? O7 Co2 O6 91.73(8) 2_574 . ? O7 Co2 O6 88.27(8) . . ? O6 Co2 O6 180.0 2_574 . ? O7 Co2 N3 91.28(9) 2_574 . ? O7 Co2 N3 88.72(9) . . ? O6 Co2 N3 88.81(8) 2_574 . ? O6 Co2 N3 91.19(9) . . ? O7 Co2 N3 88.72(9) 2_574 2_574 ? O7 Co2 N3 91.28(9) . 2_574 ? O6 Co2 N3 91.19(8) 2_574 2_574 ? O6 Co2 N3 88.81(8) . 2_574 ? N3 Co2 N3 180.0 . 2_574 ? O3 S1 O4 109.51(14) . . ? O3 S1 O2 109.89(13) . . ? O4 S1 O2 109.27(12) . . ? O3 S1 O1 109.38(13) . . ? O4 S1 O1 109.21(12) . . ? O2 S1 O1 109.56(12) . . ? H1WA O1W H1WB 109(3) . . ? H2WA O2W H2WB 109(3) . . ? H3WA O3W H3WB 96(3) . . ? H4WA O4W H4WB 113(4) . . ? H5WA O5W H5WB 132.5 . . ? Co2 O6 H6A 121(2) . . ? Co2 O6 H6B 120(2) . . ? H6A O6 H6B 105(3) . . ? Co2 O7 H7A 125(2) . . ? Co2 O7 H7B 122(2) . . ? H7A O7 H7B 108(3) . . ? Co1 O8 H8A 123(2) . . ? Co1 O8 H8B 120(2) . . ? H8A O8 H8B 110(3) . . ? Co1 O9 H9A 121(2) . . ? Co1 O9 H9B 114(2) . . ? H9A O9 H9B 108(3) . . ? C1 N1 C5 116.3(2) . . ? C1 N1 Co1 120.90(19) . . ? C5 N1 Co1 122.54(18) . . ? C11 N2 C7 126.6(2) . . ? C11 N2 H2N 119(2) . . ? C7 N2 H2N 114(2) . . ? C6 N3 C10 117.5(2) . . ? C6 N3 Co2 118.23(18) . . ? C10 N3 Co2 124.24(18) . . ? N1 C1 C2 123.3(3) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 119.8(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 117.3(3) . . ? C2 C3 C11 123.4(2) . . ? C4 C3 C11 119.3(2) . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 123.7(3) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? N3 C6 C7 123.4(3) . . ? N3 C6 H6 118.3 . . ? C7 C6 H6 118.3 . . ? C8 C7 C6 118.5(2) . . ? C8 C7 N2 125.6(2) . . ? C6 C7 N2 115.9(2) . . ? C7 C8 C9 118.2(3) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C10 C9 C8 119.9(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? N3 C10 C9 122.5(2) . . ? N3 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? O5 C11 N2 123.6(2) . . ? O5 C11 C3 120.8(2) . . ? N2 C11 C3 115.5(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 O9 Co1 N1 C1 -83.3(2) 2_655 . . . ? O9 Co1 N1 C1 96.7(2) . . . . ? O8 Co1 N1 C1 8.1(2) . . . . ? O8 Co1 N1 C1 -171.9(2) 2_655 . . . ? N1 Co1 N1 C1 168(32) 2_655 . . . ? O9 Co1 N1 C5 90.5(2) 2_655 . . . ? O9 Co1 N1 C5 -89.5(2) . . . . ? O8 Co1 N1 C5 -178.1(2) . . . . ? O8 Co1 N1 C5 1.9(2) 2_655 . . . ? N1 Co1 N1 C5 -18(32) 2_655 . . . ? O7 Co2 N3 C6 -41.0(2) 2_574 . . . ? O7 Co2 N3 C6 139.0(2) . . . . ? O6 Co2 N3 C6 -129.3(2) 2_574 . . . ? O6 Co2 N3 C6 50.7(2) . . . . ? N3 Co2 N3 C6 59(26) 2_574 . . . ? O7 Co2 N3 C10 140.0(2) 2_574 . . . ? O7 Co2 N3 C10 -40.0(2) . . . . ? O6 Co2 N3 C10 51.8(2) 2_574 . . . ? O6 Co2 N3 C10 -128.2(2) . . . . ? N3 Co2 N3 C10 -120(26) 2_574 . . . ? C5 N1 C1 C2 1.1(5) . . . . ? Co1 N1 C1 C2 175.2(3) . . . . ? N1 C1 C2 C3 -0.1(6) . . . . ? C1 C2 C3 C4 -1.0(5) . . . . ? C1 C2 C3 C11 -177.7(3) . . . . ? C2 C3 C4 C5 1.1(5) . . . . ? C11 C3 C4 C5 177.9(3) . . . . ? C1 N1 C5 C4 -1.0(5) . . . . ? Co1 N1 C5 C4 -175.0(2) . . . . ? C3 C4 C5 N1 -0.1(5) . . . . ? C10 N3 C6 C7 0.7(4) . . . . ? Co2 N3 C6 C7 -178.4(2) . . . . ? N3 C6 C7 C8 -1.8(4) . . . . ? N3 C6 C7 N2 178.6(3) . . . . ? C11 N2 C7 C8 15.8(4) . . . . ? C11 N2 C7 C6 -164.6(3) . . . . ? C6 C7 C8 C9 1.6(4) . . . . ? N2 C7 C8 C9 -178.9(3) . . . . ? C7 C8 C9 C10 -0.5(4) . . . . ? C6 N3 C10 C9 0.5(4) . . . . ? Co2 N3 C10 C9 179.5(2) . . . . ? C8 C9 C10 N3 -0.6(5) . . . . ? C7 N2 C11 O5 -7.1(5) . . . . ? C7 N2 C11 C3 172.2(2) . . . . ? C2 C3 C11 O5 151.9(3) . . . . ? C4 C3 C11 O5 -24.7(4) . . . . ? C2 C3 C11 N2 -27.4(4) . . . . ? C4 C3 C11 N2 156.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O4W 0.838(18) 1.95(2) 2.779(4) 172(4) . O1W H1WB O5 0.834(18) 1.939(19) 2.767(3) 172(3) 1_565 O2W H2WA O3 0.836(19) 2.08(2) 2.919(4) 176(4) 1_564 O2W H2WB O3W 0.851(19) 1.921(19) 2.770(4) 176(4) . O3W H3WA O4W 0.889(19) 2.11(3) 2.870(4) 143(4) . O3W H3WA O5W 0.889(19) 2.64(4) 3.287(5) 131(4) . O3W H3WB O1 0.883(19) 2.25(2) 3.066(4) 154(4) 2_574 O3W H3WB O3 0.883(19) 2.45(3) 3.193(4) 142(4) 2_574 O4W H4WA O5W 0.856(19) 1.95(3) 2.777(6) 163(5) . O4W H4WB O3 0.854(19) 2.03(2) 2.871(4) 168(5) 1_664 O5W H5WA O3 0.954(19) 1.919(17) 2.856(4) 167(3) 2_574 O5W H5WB O3 0.94 2.29 2.984(5) 129.8 1_564 O5W H5WB O4 0.94 2.40 3.330(4) 168.6 1_564 O6 H6A O2 0.850(18) 1.867(19) 2.714(3) 175(3) 2_565 O6 H6B O1W 0.829(18) 2.00(2) 2.796(3) 162(3) 2_674 O7 H7A O1W 0.848(18) 1.95(2) 2.781(3) 166(3) . O7 H7B O4 0.844(18) 1.860(19) 2.699(3) 173(4) 1_564 O8 H8A O2 0.833(18) 1.904(18) 2.728(3) 169(3) 1_655 O8 H8B O4 0.821(18) 1.917(18) 2.737(3) 176(3) . O9 H9A O1 0.849(18) 1.864(19) 2.711(3) 175(3) 2 O9 H9B O1 0.840(18) 1.930(19) 2.766(3) 173(3) . N2 H2N O2W 0.83(3) 2.02(4) 2.842(3) 167(3) 2_574 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.474 _refine_diff_density_min -0.794 _refine_diff_density_rms 0.073 data_c2c _database_code_depnum_ccdc_archive 'CCDC 896610' #TrackingRef '13294_web_deposit_cif_file_1_RobertLaDuca_1345044615.0cuso43pinafinal.cif' _audit_update_record ; 2012-06-12 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 Cu N3 O7 S' _chemical_formula_weight 394.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.075(7) _cell_length_b 9.496(3) _cell_length_c 14.226(4) _cell_angle_alpha 90.00 _cell_angle_beta 122.425(4) _cell_angle_gamma 90.00 _cell_volume 2745.2(14) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6384 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.35 _exptl_crystal_description chunk _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.911 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 1.787 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6498 _exptl_absorpt_correction_T_max 0.7642 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 173(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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10721 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.40 _reflns_number_total 2534 _reflns_number_gt 2192 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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. ; _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^)+(0.0749P)^2^+3.1309P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2534 _refine_ls_number_parameters 223 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _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 0.247651(17) 0.04550(4) 0.35342(3) 0.01560(17) Uani 1 1 d . . . S2 S 0.32022(3) -0.17397(8) 0.24928(6) 0.0138(2) Uani 1 1 d . . . O1 O 0.26251(12) -0.0291(2) 0.4953(2) 0.0213(5) Uani 1 1 d D . . H1A H 0.2313(14) -0.059(4) 0.499(3) 0.026 Uiso 1 1 d D . . H1B H 0.2782(17) 0.039(3) 0.541(3) 0.026 Uiso 1 1 d D . . O1W O 0.33503(12) -0.3817(3) 0.4830(2) 0.0261(6) Uani 1 1 d D . . H1WA H 0.3168(18) -0.362(4) 0.4153(16) 0.031 Uiso 1 1 d D . . H1WB H 0.3639(15) -0.324(3) 0.524(3) 0.031 Uiso 1 1 d D . . O2 O 0.44620(11) -0.2130(2) 0.6083(2) 0.0236(5) Uani 1 1 d . . . O3 O 0.28306(11) -0.0552(2) 0.25482(19) 0.0191(5) Uani 1 1 d . . . O4 O 0.38998(11) -0.1639(2) 0.3362(2) 0.0221(5) Uani 1 1 d . . . O5 O 0.31056(12) -0.1812(2) 0.13887(19) 0.0247(6) Uani 1 1 d . . . O6 O 0.29359(10) -0.3083(2) 0.26642(18) 0.0169(5) Uani 1 1 d . . . N1 N 0.33694(12) 0.1334(3) 0.4495(2) 0.0157(6) Uani 1 1 d . . . N2 N 0.50353(13) -0.0166(3) 0.6218(2) 0.0183(6) Uani 1 1 d D . . H2N H 0.5427(12) 0.018(4) 0.641(3) 0.022 Uiso 1 1 d D . . N3 N 0.66670(13) -0.4239(3) 0.7736(2) 0.0174(6) Uani 1 1 d . . . C1 C 0.38634(15) 0.0403(3) 0.4994(3) 0.0168(7) Uani 1 1 d . . . H1 H 0.3769 -0.0569 0.4825 0.020 Uiso 1 1 calc R . . C2 C 0.45055(15) 0.0806(3) 0.5745(3) 0.0172(7) Uani 1 1 d . . . C3 C 0.46398(15) 0.2214(4) 0.5999(3) 0.0219(7) Uani 1 1 d . . . H3 H 0.5077 0.2523 0.6513 0.026 Uiso 1 1 calc R . . C4 C 0.41292(16) 0.3163(3) 0.5495(3) 0.0246(8) Uani 1 1 d . . . H4 H 0.4211 0.4137 0.5668 0.030 Uiso 1 1 calc R . . C5 C 0.34957(15) 0.2702(3) 0.4735(3) 0.0190(7) Uani 1 1 d . . . H5 H 0.3147 0.3366 0.4381 0.023 Uiso 1 1 calc R . . C6 C 0.60572(18) -0.4733(4) 0.7052(3) 0.0291(8) Uani 1 1 d . . . H6 H 0.5998 -0.5711 0.6883 0.035 Uiso 1 1 calc R . . C7 C 0.55132(16) -0.3873(4) 0.6587(3) 0.0305(9) Uani 1 1 d . . . H7 H 0.5086 -0.4259 0.6114 0.037 Uiso 1 1 calc R . . C8 C 0.55915(15) -0.2435(3) 0.6811(3) 0.0172(6) Uani 1 1 d . . . C9 C 0.62217(15) -0.1934(3) 0.7491(3) 0.0198(7) Uani 1 1 d . . . H9 H 0.6297 -0.0956 0.7649 0.024 Uiso 1 1 calc R . . C10 C 0.67421(15) -0.2860(3) 0.7941(3) 0.0196(7) Uani 1 1 d . . . H10 H 0.7174 -0.2500 0.8419 0.024 Uiso 1 1 calc R . . C11 C 0.49799(15) -0.1562(3) 0.6332(3) 0.0175(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0135(3) 0.0121(3) 0.0161(3) 0.00105(14) 0.00460(19) -0.00199(14) S2 0.0146(4) 0.0086(4) 0.0177(4) -0.0009(3) 0.0082(3) -0.0004(3) O1 0.0225(13) 0.0197(13) 0.0188(12) -0.0032(10) 0.0090(10) -0.0081(10) O1W 0.0270(13) 0.0258(14) 0.0210(12) -0.0028(11) 0.0098(11) -0.0103(11) O2 0.0152(11) 0.0184(12) 0.0308(13) 0.0047(10) 0.0082(10) -0.0008(9) O3 0.0191(12) 0.0119(12) 0.0262(13) -0.0015(9) 0.0121(10) 0.0027(8) O4 0.0151(11) 0.0162(12) 0.0291(13) -0.0008(10) 0.0078(10) -0.0011(9) O5 0.0343(14) 0.0223(13) 0.0231(12) 0.0039(10) 0.0192(11) 0.0081(10) O6 0.0199(11) 0.0082(11) 0.0198(11) -0.0020(9) 0.0088(9) -0.0043(9) N1 0.0163(13) 0.0137(14) 0.0160(13) 0.0006(11) 0.0080(11) 0.0006(10) N2 0.0135(13) 0.0139(14) 0.0234(14) 0.0026(11) 0.0071(12) 0.0015(11) N3 0.0161(13) 0.0140(13) 0.0188(13) 0.0009(11) 0.0073(11) -0.0003(11) C1 0.0157(15) 0.0148(16) 0.0162(15) 0.0002(12) 0.0061(13) 0.0014(12) C2 0.0194(16) 0.0132(16) 0.0183(16) 0.0011(13) 0.0096(14) 0.0000(13) C3 0.0146(16) 0.0177(17) 0.0264(17) -0.0020(14) 0.0064(14) -0.0032(13) C4 0.0204(17) 0.0105(16) 0.035(2) -0.0006(14) 0.0092(15) -0.0025(13) C5 0.0181(16) 0.0125(16) 0.0239(17) 0.0026(13) 0.0096(14) 0.0015(13) C6 0.0225(18) 0.0147(17) 0.039(2) -0.0066(15) 0.0089(17) -0.0004(14) C7 0.0150(16) 0.0172(18) 0.041(2) -0.0058(16) 0.0029(15) -0.0022(14) C8 0.0162(15) 0.0146(16) 0.0182(15) 0.0024(13) 0.0075(13) 0.0014(12) C9 0.0201(17) 0.0110(16) 0.0237(17) 0.0022(13) 0.0088(14) -0.0009(13) C10 0.0147(15) 0.0131(16) 0.0254(17) 0.0017(14) 0.0070(13) -0.0025(12) C11 0.0166(15) 0.0167(17) 0.0167(15) 0.0014(13) 0.0073(13) -0.0001(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.982(2) . ? Cu1 O6 2.001(2) 4 ? Cu1 N1 2.009(3) . ? Cu1 N3 2.012(3) 8_445 ? Cu1 O3 2.212(2) . ? S2 O4 1.460(2) . ? S2 O5 1.461(2) . ? S2 O3 1.468(2) . ? S2 O6 1.505(2) . ? O1 H1A 0.829(18) . ? O1 H1B 0.851(18) . ? O1W H1WA 0.839(18) . ? O1W H1WB 0.827(18) . ? O2 C11 1.224(4) . ? O6 Cu1 2.001(2) 4_545 ? N1 C5 1.337(4) . ? N1 C1 1.340(4) . ? N2 C11 1.351(4) . ? N2 C2 1.418(4) . ? N2 H2N 0.892(18) . ? N3 C10 1.333(4) . ? N3 C6 1.338(4) . ? N3 Cu1 2.012(3) 8_546 ? C1 C2 1.381(4) . ? C1 H1 0.9500 . ? C2 C3 1.378(5) . ? C3 C4 1.376(5) . ? C3 H3 0.9500 . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.375(5) . ? C6 H6 0.9500 . ? C7 C8 1.393(5) . ? C7 H7 0.9500 . ? C8 C9 1.375(4) . ? C8 C11 1.498(4) . ? C9 C10 1.376(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O6 148.40(10) . 4 ? O1 Cu1 N1 84.98(10) . . ? O6 Cu1 N1 98.78(10) 4 . ? O1 Cu1 N3 87.75(10) . 8_445 ? O6 Cu1 N3 91.68(10) 4 8_445 ? N1 Cu1 N3 169.08(11) . 8_445 ? O1 Cu1 O3 124.80(9) . . ? O6 Cu1 O3 86.76(9) 4 . ? N1 Cu1 O3 88.59(10) . . ? N3 Cu1 O3 88.87(10) 8_445 . ? O4 S2 O5 111.20(14) . . ? O4 S2 O3 111.19(14) . . ? O5 S2 O3 110.09(13) . . ? O4 S2 O6 108.33(13) . . ? O5 S2 O6 107.36(13) . . ? O3 S2 O6 108.54(12) . . ? Cu1 O1 H1A 121(3) . . ? Cu1 O1 H1B 105(3) . . ? H1A O1 H1B 105(3) . . ? H1WA O1W H1WB 112(3) . . ? S2 O3 Cu1 145.04(14) . . ? S2 O6 Cu1 120.65(13) . 4_545 ? C5 N1 C1 119.4(3) . . ? C5 N1 Cu1 126.3(2) . . ? C1 N1 Cu1 114.1(2) . . ? C11 N2 C2 125.0(3) . . ? C11 N2 H2N 119(3) . . ? C2 N2 H2N 116(3) . . ? C10 N3 C6 118.1(3) . . ? C10 N3 Cu1 117.6(2) . 8_546 ? C6 N3 Cu1 124.2(2) . 8_546 ? N1 C1 C2 122.3(3) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 118.7(3) . . ? C3 C2 N2 118.8(3) . . ? C1 C2 N2 122.4(3) . . ? C4 C3 C2 118.7(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 120.7(3) . . ? N1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? N3 C6 C7 122.2(3) . . ? N3 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C6 C7 C8 119.7(3) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 117.6(3) . . ? C9 C8 C11 125.0(3) . . ? C7 C8 C11 117.3(3) . . ? C8 C9 C10 119.5(3) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? N3 C10 C9 122.9(3) . . ? N3 C10 H10 118.5 . . ? C9 C10 H10 118.5 . . ? O2 C11 N2 123.3(3) . . ? O2 C11 C8 119.2(3) . . ? N2 C11 C8 117.5(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 O4 S2 O3 Cu1 -67.7(3) . . . . ? O5 S2 O3 Cu1 168.6(2) . . . . ? O6 S2 O3 Cu1 51.3(3) . . . . ? O1 Cu1 O3 S2 -1.4(3) . . . . ? O6 Cu1 O3 S2 -179.6(2) 4 . . . ? N1 Cu1 O3 S2 81.5(3) . . . . ? N3 Cu1 O3 S2 -87.9(3) 8_445 . . . ? O4 S2 O6 Cu1 -121.50(15) . . . 4_545 ? O5 S2 O6 Cu1 -1.32(18) . . . 4_545 ? O3 S2 O6 Cu1 117.65(15) . . . 4_545 ? O1 Cu1 N1 C5 -107.9(3) . . . . ? O6 Cu1 N1 C5 40.5(3) 4 . . . ? N3 Cu1 N1 C5 -156.4(5) 8_445 . . . ? O3 Cu1 N1 C5 127.0(3) . . . . ? O1 Cu1 N1 C1 66.4(2) . . . . ? O6 Cu1 N1 C1 -145.2(2) 4 . . . ? N3 Cu1 N1 C1 17.9(7) 8_445 . . . ? O3 Cu1 N1 C1 -58.7(2) . . . . ? C5 N1 C1 C2 -0.7(5) . . . . ? Cu1 N1 C1 C2 -175.4(2) . . . . ? N1 C1 C2 C3 0.8(5) . . . . ? N1 C1 C2 N2 -175.7(3) . . . . ? C11 N2 C2 C3 158.8(3) . . . . ? C11 N2 C2 C1 -24.7(5) . . . . ? C1 C2 C3 C4 0.0(5) . . . . ? N2 C2 C3 C4 176.7(3) . . . . ? C2 C3 C4 C5 -0.9(5) . . . . ? C1 N1 C5 C4 -0.3(5) . . . . ? Cu1 N1 C5 C4 173.8(2) . . . . ? C3 C4 C5 N1 1.1(5) . . . . ? C10 N3 C6 C7 -1.7(5) . . . . ? Cu1 N3 C6 C7 175.3(3) 8_546 . . . ? N3 C6 C7 C8 1.1(6) . . . . ? C6 C7 C8 C9 0.7(5) . . . . ? C6 C7 C8 C11 -176.7(3) . . . . ? C7 C8 C9 C10 -1.6(5) . . . . ? C11 C8 C9 C10 175.5(3) . . . . ? C6 N3 C10 C9 0.7(5) . . . . ? Cu1 N3 C10 C9 -176.5(3) 8_546 . . . ? C8 C9 C10 N3 1.0(5) . . . . ? C2 N2 C11 O2 -3.7(5) . . . . ? C2 N2 C11 C8 177.6(3) . . . . ? C9 C8 C11 O2 -154.4(3) . . . . ? C7 C8 C11 O2 22.7(5) . . . . ? C9 C8 C11 N2 24.4(5) . . . . ? C7 C8 C11 N2 -158.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O1W 0.829(18) 1.838(19) 2.666(3) 175(4) 7_546 O1 H1B O5 0.851(18) 1.789(19) 2.639(3) 178(4) 6_556 O1W H1WA O6 0.839(18) 1.95(2) 2.771(3) 168(4) . O1W H1WB O2 0.827(18) 1.98(2) 2.791(3) 165(4) . N2 H2N O4 0.892(18) 2.02(2) 2.868(4) 158(3) 5_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.088 _refine_diff_density_min -0.937 _refine_diff_density_rms 0.126 data_p21c _database_code_depnum_ccdc_archive 'CCDC 896611' #TrackingRef '13295_web_deposit_cif_file_2_RobertLaDuca_1345044615.0cdso43pinafinal.cif' _audit_update_record ; 2012-01-26 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 Cd N3 O6 S' _chemical_formula_weight 425.69 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 monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6706(8) _cell_length_b 21.5919(19) _cell_length_c 6.9169(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.1710(10) _cell_angle_gamma 90.00 _cell_volume 1294.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4704 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.43 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.884 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7113 _exptl_absorpt_correction_T_max 0.9018 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 173(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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10565 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.45 _reflns_number_total 2408 _reflns_number_gt 1980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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. ; _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^)+(0.0355P)^2^+0.1123P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2408 _refine_ls_number_parameters 208 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0750 _refine_ls_wR_factor_gt 0.0706 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.15016(3) 0.452848(13) 0.73081(4) 0.01491(12) Uani 1 1 d . . . S1 S 0.18633(11) 0.46880(5) 1.23689(14) 0.0133(2) Uani 1 1 d . . . O1 O 0.1126(3) 0.43875(13) 1.0697(4) 0.0198(7) Uani 1 1 d . . . O2 O 0.1890(3) 0.42559(13) 1.4032(4) 0.0186(6) Uani 1 1 d . . . O3 O 0.3459(3) 0.48555(13) 1.1856(4) 0.0192(7) Uani 1 1 d . . . O6 O 0.4087(3) 0.42979(14) 0.8343(4) 0.0204(7) Uani 1 1 d D . . H6A H 0.489(4) 0.4497(18) 0.801(6) 0.024 Uiso 1 1 d D . . H6B H 0.392(5) 0.438(2) 0.950(3) 0.024 Uiso 1 1 d D . . O4 O 0.1015(3) 0.52498(13) 1.2947(4) 0.0191(7) Uani 1 1 d . . . O5 O 0.4945(3) 0.75939(13) 0.8396(5) 0.0260(7) Uani 1 1 d . . . N1 N 0.2530(4) 0.55150(14) 0.7289(5) 0.0165(8) Uani 1 1 d . . . N2 N 0.6940(4) 0.70035(15) 0.7303(5) 0.0159(8) Uani 1 1 d D . . H2N H 0.732(5) 0.6630(11) 0.707(6) 0.019 Uiso 1 1 d D . . N3 N 0.9052(4) 0.84831(15) 0.7637(5) 0.0157(7) Uani 1 1 d . . . C11 C 0.5451(5) 0.71075(19) 0.7779(6) 0.0187(9) Uani 1 1 d . . . C9 C 1.0489(5) 0.82722(19) 0.7902(6) 0.0181(9) Uani 1 1 d . . . H9 H 1.1298 0.8563 0.8084 0.022 Uiso 1 1 calc R . . C6 C 0.8163(5) 0.74335(18) 0.7485(6) 0.0142(9) Uani 1 1 d . . . C4 C 0.3355(4) 0.64214(19) 0.8983(6) 0.0168(9) Uani 1 1 d . . . H4 H 0.3256 0.6686 1.0072 0.020 Uiso 1 1 calc R . . C2 C 0.4491(5) 0.61677(19) 0.5956(6) 0.0178(9) Uani 1 1 d . . . H2 H 0.5171 0.6257 0.4918 0.021 Uiso 1 1 calc R . . C8 C 1.0842(5) 0.76500(19) 0.7921(6) 0.0215(10) Uani 1 1 d . . . H8 H 1.1880 0.7517 0.8069 0.026 Uiso 1 1 calc R . . C3 C 0.4421(5) 0.65522(17) 0.7550(6) 0.0145(9) Uani 1 1 d . . . C5 C 0.2440(5) 0.59014(19) 0.8807(6) 0.0196(10) Uani 1 1 d . . . H5 H 0.1717 0.5813 0.9799 0.024 Uiso 1 1 calc R . . C1 C 0.3561(5) 0.5656(2) 0.5905(6) 0.0206(10) Uani 1 1 d . . . H1 H 0.3646 0.5385 0.4830 0.025 Uiso 1 1 calc R . . C7 C 0.9657(5) 0.72187(19) 0.7719(6) 0.0181(9) Uani 1 1 d . . . H7 H 0.9869 0.6787 0.7742 0.022 Uiso 1 1 calc R . . C10 C 0.7904(5) 0.80668(18) 0.7429(6) 0.0158(9) Uani 1 1 d . . . H10 H 0.6882 0.8213 0.7238 0.019 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 0.01483(18) 0.01225(18) 0.01764(18) -0.00014(13) 0.00051(12) -0.00059(12) S1 0.0137(5) 0.0132(5) 0.0130(5) -0.0002(4) 0.0017(4) 0.0002(4) O1 0.0180(16) 0.0254(17) 0.0160(16) -0.0007(13) 0.0000(12) -0.0049(13) O2 0.0226(16) 0.0191(16) 0.0140(15) 0.0029(13) 0.0040(12) 0.0032(13) O3 0.0167(15) 0.0230(16) 0.0181(15) -0.0039(14) 0.0004(12) -0.0037(13) O6 0.0147(16) 0.0243(17) 0.0222(17) -0.0020(14) 0.0037(13) -0.0020(13) O4 0.0166(15) 0.0155(15) 0.0253(17) -0.0034(13) 0.0000(13) 0.0056(12) O5 0.0219(17) 0.0158(16) 0.040(2) -0.0093(15) 0.0106(14) -0.0028(13) N1 0.0154(18) 0.0101(18) 0.024(2) 0.0004(16) -0.0007(15) -0.0023(14) N2 0.0156(18) 0.0091(17) 0.023(2) 0.0008(15) 0.0022(15) -0.0008(14) N3 0.0185(18) 0.0127(18) 0.0160(18) 0.0000(15) -0.0008(14) -0.0006(15) C11 0.023(2) 0.017(2) 0.016(2) -0.0009(19) -0.0025(18) -0.0014(19) C9 0.016(2) 0.018(2) 0.020(2) 0.0000(19) 0.0008(17) -0.0067(18) C6 0.015(2) 0.014(2) 0.014(2) -0.0026(17) -0.0011(17) -0.0036(17) C4 0.014(2) 0.015(2) 0.021(2) -0.0026(18) 0.0018(17) 0.0063(17) C2 0.016(2) 0.018(2) 0.019(2) 0.0009(18) 0.0056(17) -0.0005(18) C8 0.016(2) 0.018(2) 0.031(3) 0.001(2) -0.0006(19) 0.0018(18) C3 0.015(2) 0.010(2) 0.019(2) 0.0013(17) -0.0036(17) 0.0056(16) C5 0.019(2) 0.017(2) 0.022(2) 0.0036(19) 0.0043(18) 0.0026(18) C1 0.020(2) 0.023(2) 0.020(2) -0.0061(19) -0.0027(18) -0.0023(19) C7 0.019(2) 0.016(2) 0.020(2) -0.0004(18) 0.0026(18) 0.0040(18) C10 0.014(2) 0.016(2) 0.017(2) -0.0006(18) 0.0044(17) -0.0015(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 Cd1 O4 2.241(3) 3_567 ? Cd1 N3 2.308(3) 2_646 ? Cd1 N1 2.309(3) . ? Cd1 O2 2.366(3) 1_554 ? Cd1 O1 2.387(3) . ? Cd1 O6 2.403(3) . ? S1 O1 1.470(3) . ? S1 O3 1.474(3) . ? S1 O4 1.474(3) . ? S1 O2 1.481(3) . ? O2 Cd1 2.366(3) 1_556 ? O6 H6A 0.848(19) . ? O6 H6B 0.835(18) . ? O4 Cd1 2.241(3) 3_567 ? O5 C11 1.216(5) . ? N1 C5 1.343(5) . ? N1 C1 1.346(5) . ? N2 C11 1.352(5) . ? N2 C6 1.415(5) . ? N2 H2N 0.886(19) . ? N3 C9 1.338(5) . ? N3 C10 1.348(5) . ? N3 Cd1 2.308(3) 2_656 ? C11 C3 1.503(6) . ? C9 C8 1.378(6) . ? C9 H9 0.9500 . ? C6 C7 1.385(6) . ? C6 C10 1.386(5) . ? C4 C5 1.380(6) . ? C4 C3 1.386(5) . ? C4 H4 0.9500 . ? C2 C1 1.368(6) . ? C2 C3 1.382(6) . ? C2 H2 0.9500 . ? C8 C7 1.394(6) . ? C8 H8 0.9500 . ? C5 H5 0.9500 . ? C1 H1 0.9500 . ? C7 H7 0.9500 . ? C10 H10 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cd1 N3 90.44(11) 3_567 2_646 ? O4 Cd1 N1 100.28(11) 3_567 . ? N3 Cd1 N1 169.27(12) 2_646 . ? O4 Cd1 O2 96.83(10) 3_567 1_554 ? N3 Cd1 O2 78.62(11) 2_646 1_554 ? N1 Cd1 O2 99.67(11) . 1_554 ? O4 Cd1 O1 88.22(10) 3_567 . ? N3 Cd1 O1 80.22(10) 2_646 . ? N1 Cd1 O1 100.20(11) . . ? O2 Cd1 O1 158.27(10) 1_554 . ? O4 Cd1 O6 167.19(10) 3_567 . ? N3 Cd1 O6 89.22(11) 2_646 . ? N1 Cd1 O6 80.38(11) . . ? O2 Cd1 O6 95.65(10) 1_554 . ? O1 Cd1 O6 79.11(10) . . ? O1 S1 O3 108.96(16) . . ? O1 S1 O4 111.12(17) . . ? O3 S1 O4 109.42(17) . . ? O1 S1 O2 109.78(17) . . ? O3 S1 O2 109.22(17) . . ? O4 S1 O2 108.31(17) . . ? S1 O1 Cd1 130.97(16) . . ? S1 O2 Cd1 125.81(16) . 1_556 ? Cd1 O6 H6A 125(3) . . ? Cd1 O6 H6B 95(3) . . ? H6A O6 H6B 107(3) . . ? S1 O4 Cd1 129.86(17) . 3_567 ? C5 N1 C1 117.1(3) . . ? C5 N1 Cd1 123.0(3) . . ? C1 N1 Cd1 118.0(3) . . ? C11 N2 C6 125.8(3) . . ? C11 N2 H2N 124(3) . . ? C6 N2 H2N 109(3) . . ? C9 N3 C10 118.3(3) . . ? C9 N3 Cd1 121.6(3) . 2_656 ? C10 N3 Cd1 120.0(3) . 2_656 ? O5 C11 N2 125.1(4) . . ? O5 C11 C3 120.8(4) . . ? N2 C11 C3 114.1(4) . . ? N3 C9 C8 122.7(4) . . ? N3 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? C7 C6 C10 119.0(4) . . ? C7 C6 N2 119.4(4) . . ? C10 C6 N2 121.6(4) . . ? C5 C4 C3 119.2(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C1 C2 C3 118.6(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C9 C8 C7 119.1(4) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C2 C3 C4 118.6(4) . . ? C2 C3 C11 122.4(4) . . ? C4 C3 C11 119.0(4) . . ? N1 C5 C4 122.6(4) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? N1 C1 C2 123.8(4) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C6 C7 C8 118.5(4) . . ? C6 C7 H7 120.8 . . ? C8 C7 H7 120.8 . . ? N3 C10 C6 122.4(4) . . ? N3 C10 H10 118.8 . . ? C6 C10 H10 118.8 . . ? 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 S1 O1 Cd1 -31.1(3) . . . . ? O4 S1 O1 Cd1 89.6(2) . . . . ? O2 S1 O1 Cd1 -150.6(2) . . . . ? O4 Cd1 O1 S1 -122.8(2) 3_567 . . . ? N3 Cd1 O1 S1 146.4(2) 2_646 . . . ? N1 Cd1 O1 S1 -22.7(2) . . . . ? O2 Cd1 O1 S1 133.1(2) 1_554 . . . ? O6 Cd1 O1 S1 55.3(2) . . . . ? O1 S1 O2 Cd1 -142.09(19) . . . 1_556 ? O3 S1 O2 Cd1 98.5(2) . . . 1_556 ? O4 S1 O2 Cd1 -20.6(2) . . . 1_556 ? O1 S1 O4 Cd1 30.1(3) . . . 3_567 ? O3 S1 O4 Cd1 150.5(2) . . . 3_567 ? O2 S1 O4 Cd1 -90.6(2) . . . 3_567 ? O4 Cd1 N1 C5 74.0(3) 3_567 . . . ? N3 Cd1 N1 C5 -107.3(6) 2_646 . . . ? O2 Cd1 N1 C5 172.8(3) 1_554 . . . ? O1 Cd1 N1 C5 -16.0(3) . . . . ? O6 Cd1 N1 C5 -93.0(3) . . . . ? O4 Cd1 N1 C1 -122.0(3) 3_567 . . . ? N3 Cd1 N1 C1 56.7(8) 2_646 . . . ? O2 Cd1 N1 C1 -23.1(3) 1_554 . . . ? O1 Cd1 N1 C1 148.0(3) . . . . ? O6 Cd1 N1 C1 71.0(3) . . . . ? C6 N2 C11 O5 1.7(7) . . . . ? C6 N2 C11 C3 -176.3(4) . . . . ? C10 N3 C9 C8 1.7(6) . . . . ? Cd1 N3 C9 C8 178.4(3) 2_656 . . . ? C11 N2 C6 C7 153.7(4) . . . . ? C11 N2 C6 C10 -26.5(6) . . . . ? N3 C9 C8 C7 -2.1(7) . . . . ? C1 C2 C3 C4 -3.3(6) . . . . ? C1 C2 C3 C11 177.1(4) . . . . ? C5 C4 C3 C2 2.3(6) . . . . ? C5 C4 C3 C11 -178.1(4) . . . . ? O5 C11 C3 C2 138.3(4) . . . . ? N2 C11 C3 C2 -43.6(6) . . . . ? O5 C11 C3 C4 -41.3(6) . . . . ? N2 C11 C3 C4 136.7(4) . . . . ? C1 N1 C5 C4 -0.4(6) . . . . ? Cd1 N1 C5 C4 163.8(3) . . . . ? C3 C4 C5 N1 -0.4(6) . . . . ? C5 N1 C1 C2 -0.7(6) . . . . ? Cd1 N1 C1 C2 -165.7(3) . . . . ? C3 C2 C1 N1 2.6(6) . . . . ? C10 C6 C7 C8 1.0(6) . . . . ? N2 C6 C7 C8 -179.2(4) . . . . ? C9 C8 C7 C6 0.7(6) . . . . ? C9 N3 C10 C6 0.1(6) . . . . ? Cd1 N3 C10 C6 -176.7(3) 2_656 . . . ? C7 C6 C10 N3 -1.4(6) . . . . ? N2 C6 C10 N3 178.7(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O2 0.886(19) 2.17(2) 3.047(4) 170(4) 3_667 O6 H6B O3 0.835(18) 1.97(2) 2.767(4) 160(4) . O6 H6A O3 0.848(19) 2.00(2) 2.809(4) 158(4) 3_667 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.570 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.118