# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_compound_1 _database_code_depnum_ccdc_archive 'CCDC 931662' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H18 Ca Cu N2 O12 S, H O0.50, H O0.50' _chemical_formula_sum 'C11 H20 Ca Cu N2 O13 S' _chemical_formula_weight 523.97 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' Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.927(2) _cell_length_b 9.233(2) _cell_length_c 12.683(3) _cell_angle_alpha 94.158(4) _cell_angle_beta 96.911(4) _cell_angle_gamma 104.064(5) _cell_volume 1001.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2531 _cell_measurement_theta_min 2.849 _cell_measurement_theta_max 26.846 _exptl_crystal_description Block _exptl_crystal_colour violet _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 538 _exptl_absorpt_coefficient_mu 1.519 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6185 _exptl_absorpt_correction_T_max 0.6586 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 Smart Aepex CCD' _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 4994 _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3472 _reflns_number_gt 2946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0568P)^2^+1.6800P] 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 3472 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.64027(6) 1.09382(6) 0.64289(4) 0.03032(18) Uani 1 1 d . . . C1 C 0.7683(5) 0.9029(5) 0.5127(3) 0.0293(9) Uani 1 1 d . . . C2 C 0.8111(6) 0.7683(5) 0.4946(3) 0.0365(10) Uani 1 1 d . . . H2 H 0.7985 0.6998 0.5452 0.044 Uiso 1 1 calc R . . C3 C 0.8713(5) 0.7347(5) 0.4038(3) 0.0360(10) Uani 1 1 d . . . H3 H 0.8988 0.6443 0.3937 0.043 Uiso 1 1 calc R . . C4 C 0.8912(5) 0.8346(5) 0.3278(3) 0.0293(9) Uani 1 1 d . . . C5 C 0.8515(5) 0.9678(5) 0.3433(3) 0.0311(9) Uani 1 1 d . . . H5 H 0.8668 1.0354 0.2923 0.037 Uiso 1 1 calc R . . C6 C 0.7884(5) 1.0044(5) 0.4344(3) 0.0286(9) Uani 1 1 d . . . C7 C 0.7493(5) 1.1476(5) 0.4422(3) 0.0325(10) Uani 1 1 d . . . H7 H 0.7710 1.2087 0.3879 0.039 Uiso 1 1 calc R . . C8 C 0.6512(6) 1.3417(5) 0.5224(4) 0.0405(11) Uani 1 1 d . . . H8A H 0.5741 1.3430 0.4619 0.049 Uiso 1 1 calc R . . H8B H 0.7447 1.4194 0.5180 0.049 Uiso 1 1 calc R . . C9 C 0.5882(5) 1.3732(5) 0.6264(3) 0.0292(9) Uani 1 1 d . . . C10 C 0.5164(5) 1.2675(5) 0.7866(3) 0.0333(10) Uani 1 1 d . . . H10A H 0.4130 1.2849 0.7807 0.040 Uiso 1 1 calc R . . H10B H 0.5875 1.3488 0.8341 0.040 Uiso 1 1 calc R . . C11 C 0.5143(5) 1.1197(5) 0.8300(3) 0.0310(9) Uani 1 1 d . . . N1 N 0.6871(4) 1.1962(4) 0.5184(3) 0.0333(8) Uani 1 1 d . . . N2 N 0.5668(4) 1.2612(4) 0.6825(3) 0.0299(8) Uani 1 1 d . . . S1 S 0.95721(12) 0.78295(13) 0.20841(8) 0.0324(3) Uani 1 1 d . . . O5 O 0.8397(4) 0.6511(4) 0.1575(3) 0.0466(8) Uani 1 1 d . . . O6 O 1.1054(4) 0.7506(5) 0.2362(3) 0.0547(10) Uani 1 1 d . . . O7 O 0.9682(4) 0.9094(4) 0.1459(3) 0.0495(9) Uani 1 1 d . . . O1 O 0.7084(4) 0.9246(3) 0.6006(2) 0.0371(7) Uani 1 1 d . . . O2 O 0.5616(4) 1.4992(3) 0.6463(3) 0.0428(8) Uani 1 1 d . . . O3 O 0.5543(4) 1.0181(3) 0.7732(2) 0.0351(7) Uani 1 1 d . . . O4 O 0.4764(4) 1.0965(4) 0.9192(2) 0.0434(8) Uani 1 1 d . . . Ca1 Ca 0.53388(10) 0.81969(9) 0.89520(6) 0.0274(2) Uani 1 1 d . . . O8 O 0.7100(4) 0.7586(4) 0.7703(3) 0.0429(8) Uani 1 1 d . . . H8D H 0.6654 0.6668 0.7510 0.064 Uiso 1 1 d R . . H8C H 0.6993 0.8097 0.7178 0.064 Uiso 1 1 d R . . O9 O 0.7900(3) 0.9758(3) 0.9685(2) 0.0377(7) Uani 1 1 d . . . H9A H 0.8512 1.0223 0.9294 0.057 Uiso 1 1 d R . . H9B H 0.8410 0.9525 1.0228 0.057 Uiso 1 1 d R . . O10 O 0.3784(4) 0.6054(4) 0.7721(3) 0.0499(9) Uani 1 1 d . . . H10C H 0.4303 0.5618 0.7343 0.075 Uiso 1 1 d R . . H10D H 0.3070 0.5401 0.7933 0.075 Uiso 1 1 d R . . O11 O 0.2643(5) 0.7833(5) 0.9108(4) 0.0899(18) Uani 1 1 d . . . H11B H 0.2526 0.8503 0.9564 0.135 Uiso 1 1 d R . . H11A H 0.2152 0.7898 0.8503 0.135 Uiso 1 1 d R . . O12 O 0.6220(4) 0.6224(4) 0.9777(3) 0.0466(8) Uani 1 1 d . . . H12A H 0.6714 0.6575 1.0432 0.070 Uiso 1 1 d R . . H12B H 0.6872 0.5913 0.9389 0.070 Uiso 1 1 d R . . O1W O 0.1389(11) 0.5302(13) 0.0813(10) 0.113(4) Uani 0.50 1 d P . . H1W1 H 0.0487 0.4603 0.0676 0.169 Uiso 0.50 1 d PR . . H1W2 H 0.1238 0.6182 0.0649 0.169 Uiso 0.50 1 d PR . . O2W O 0.0016(8) 0.3554(12) 0.2362(8) 0.083(3) Uani 0.50 1 d P . . H2W1 H 0.0104 0.3684 0.1682 0.124 Uiso 0.50 1 d PR . . H2W2 H 0.0243 0.2698 0.2510 0.124 Uiso 0.50 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 0.0407(3) 0.0318(3) 0.0260(3) 0.0075(2) 0.0172(2) 0.0164(2) C1 0.031(2) 0.033(2) 0.024(2) -0.0005(17) 0.0079(17) 0.0075(18) C2 0.051(3) 0.033(2) 0.030(2) 0.0060(18) 0.015(2) 0.014(2) C3 0.046(3) 0.035(2) 0.031(2) -0.0023(18) 0.012(2) 0.015(2) C4 0.028(2) 0.036(2) 0.024(2) -0.0026(17) 0.0086(17) 0.0072(18) C5 0.036(2) 0.034(2) 0.025(2) 0.0048(17) 0.0116(18) 0.0080(19) C6 0.030(2) 0.030(2) 0.025(2) 0.0010(16) 0.0081(17) 0.0046(17) C7 0.043(3) 0.034(2) 0.023(2) 0.0089(17) 0.0138(18) 0.0087(19) C8 0.067(3) 0.034(2) 0.033(2) 0.0133(19) 0.024(2) 0.026(2) C9 0.032(2) 0.030(2) 0.028(2) 0.0018(17) 0.0068(17) 0.0122(18) C10 0.038(2) 0.040(2) 0.030(2) 0.0034(18) 0.0155(18) 0.020(2) C11 0.029(2) 0.040(2) 0.028(2) 0.0054(18) 0.0085(18) 0.0129(19) N1 0.046(2) 0.033(2) 0.0271(18) 0.0069(15) 0.0154(16) 0.0149(17) N2 0.037(2) 0.0316(19) 0.0273(18) 0.0052(15) 0.0155(15) 0.0151(16) S1 0.0279(6) 0.0452(7) 0.0251(5) -0.0036(4) 0.0095(4) 0.0103(5) O5 0.045(2) 0.056(2) 0.0342(17) -0.0116(15) 0.0102(15) 0.0062(16) O6 0.0389(19) 0.085(3) 0.043(2) -0.0131(18) 0.0055(16) 0.0271(19) O7 0.054(2) 0.065(2) 0.0358(18) 0.0088(16) 0.0234(16) 0.0184(18) O1 0.059(2) 0.0319(16) 0.0296(16) 0.0077(12) 0.0247(14) 0.0188(15) O2 0.065(2) 0.0335(18) 0.0386(18) 0.0049(14) 0.0222(16) 0.0209(16) O3 0.0433(18) 0.0393(17) 0.0305(16) 0.0097(13) 0.0201(14) 0.0161(14) O4 0.055(2) 0.056(2) 0.0283(17) 0.0121(14) 0.0226(15) 0.0215(17) Ca1 0.0295(5) 0.0286(5) 0.0257(4) 0.0029(3) 0.0103(3) 0.0074(3) O8 0.055(2) 0.0369(18) 0.0416(18) 0.0070(14) 0.0219(16) 0.0128(15) O9 0.0316(17) 0.0480(19) 0.0338(16) 0.0044(14) 0.0125(13) 0.0068(14) O10 0.044(2) 0.050(2) 0.052(2) -0.0146(16) 0.0175(16) 0.0054(16) O11 0.039(2) 0.087(3) 0.130(4) -0.061(3) 0.018(2) 0.010(2) O12 0.066(2) 0.0387(18) 0.0344(17) 0.0036(14) 0.0024(16) 0.0150(17) O1W 0.064(6) 0.108(8) 0.160(11) -0.078(8) 0.007(6) 0.041(6) O2W 0.029(4) 0.117(8) 0.094(7) -0.002(6) -0.015(4) 0.020(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 Cu1 O1 1.876(3) . ? Cu1 N2 1.879(3) . ? Cu1 O3 2.005(3) . ? C1 O1 1.315(5) . ? C1 C2 1.399(6) . ? C1 C6 1.412(6) . ? C2 C3 1.374(6) . ? C2 H2 0.9300 . ? C3 C4 1.379(6) . ? C3 H3 0.9300 . ? C4 C5 1.368(6) . ? C4 S1 1.765(4) . ? C5 C6 1.400(6) . ? C5 H5 0.9300 . ? C6 C7 1.447(6) . ? C7 N1 1.277(5) . ? C7 H7 0.9300 . ? C8 N1 1.453(6) . ? C8 C9 1.530(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O2 1.256(5) . ? C9 N2 1.287(5) . ? C10 N2 1.447(5) . ? C10 C11 1.505(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O4 1.237(5) . ? C11 O3 1.286(5) . ? C11 Ca1 2.986(4) . ? S1 O6 1.435(4) . ? S1 O7 1.449(4) . ? S1 O5 1.450(3) . ? O3 Ca1 2.470(3) . ? O4 Ca1 2.444(3) 2_677 ? O4 Ca1 2.730(4) . ? Ca1 O11 2.382(4) . ? Ca1 O12 2.410(3) . ? Ca1 O9 2.421(3) . ? Ca1 O4 2.444(3) 2_677 ? Ca1 O10 2.444(3) . ? Ca1 O8 2.490(3) . ? Ca1 H8D 2.7680 . ? Ca1 H11B 2.7870 . ? Ca1 H11A 2.7752 . ? O8 H8D 0.8476 . ? O8 H8C 0.8533 . ? O9 H9A 0.8421 . ? O9 H9B 0.8496 . ? O10 H10C 0.8499 . ? O10 H10D 0.8483 . ? O11 H11B 0.8500 . ? O11 H11A 0.8500 . ? O12 H12A 0.8900 . ? O12 H12B 0.8899 . ? O1W H1W1 0.8901 . ? O1W H1W2 0.8900 . ? O2W H2W1 0.8901 . ? O2W H2W2 0.8900 . ? 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 N2 178.39(15) . . ? O1 Cu1 O3 97.01(12) . . ? N2 Cu1 O3 83.19(13) . . ? O1 C1 C2 117.6(4) . . ? O1 C1 C6 124.5(4) . . ? C2 C1 C6 117.9(4) . . ? C3 C2 C1 121.6(4) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 120.2(4) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.8(4) . . ? C5 C4 S1 121.1(3) . . ? C3 C4 S1 119.1(3) . . ? C4 C5 C6 121.3(4) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 119.2(4) . . ? C5 C6 C7 116.7(4) . . ? C1 C6 C7 124.0(4) . . ? N1 C7 C6 124.7(4) . . ? N1 C7 H7 117.7 . . ? C6 C7 H7 117.7 . . ? N1 C8 C9 110.2(3) . . ? N1 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O2 C9 N2 128.1(4) . . ? O2 C9 C8 118.5(4) . . ? N2 C9 C8 113.3(4) . . ? N2 C10 C11 107.9(3) . . ? N2 C10 H10A 110.1 . . ? C11 C10 H10A 110.1 . . ? N2 C10 H10B 110.1 . . ? C11 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? O4 C11 O3 120.4(4) . . ? O4 C11 C10 120.8(4) . . ? O3 C11 C10 118.8(3) . . ? O4 C11 Ca1 66.1(2) . . ? O3 C11 Ca1 54.4(2) . . ? C10 C11 Ca1 172.9(3) . . ? C7 N1 C8 122.2(4) . . ? C9 N2 C10 123.3(4) . . ? C9 N2 Cu1 119.3(3) . . ? C10 N2 Cu1 116.4(3) . . ? O6 S1 O7 112.4(2) . . ? O6 S1 O5 111.8(2) . . ? O7 S1 O5 112.2(2) . . ? O6 S1 C4 107.9(2) . . ? O7 S1 C4 106.4(2) . . ? O5 S1 C4 105.68(19) . . ? C1 O1 Cu1 126.0(3) . . ? C11 O3 Cu1 112.5(3) . . ? C11 O3 Ca1 100.5(2) . . ? Cu1 O3 Ca1 145.54(15) . . ? C11 O4 Ca1 151.9(3) . 2_677 ? C11 O4 Ca1 89.5(3) . . ? Ca1 O4 Ca1 112.84(12) 2_677 . ? O11 Ca1 O12 107.64(17) . . ? O11 Ca1 O9 142.21(12) . . ? O12 Ca1 O9 84.88(12) . . ? O11 Ca1 O4 74.05(15) . 2_677 ? O12 Ca1 O4 81.85(11) . 2_677 ? O9 Ca1 O4 72.69(11) . 2_677 ? O11 Ca1 O10 69.93(13) . . ? O12 Ca1 O10 81.12(13) . . ? O9 Ca1 O10 147.83(11) . . ? O4 Ca1 O10 132.83(12) 2_677 . ? O11 Ca1 O3 97.73(17) . . ? O12 Ca1 O3 152.97(12) . . ? O9 Ca1 O3 80.55(11) . . ? O4 Ca1 O3 114.79(11) 2_677 . ? O10 Ca1 O3 99.50(12) . . ? O11 Ca1 O8 141.39(14) . . ? O12 Ca1 O8 78.49(12) . . ? O9 Ca1 O8 75.24(11) . . ? O4 Ca1 O8 143.56(12) 2_677 . ? O10 Ca1 O8 73.66(11) . . ? O3 Ca1 O8 75.84(10) . . ? O11 Ca1 O4 72.46(14) . . ? O12 Ca1 O4 147.94(11) . . ? O9 Ca1 O4 78.46(11) . . ? O4 Ca1 O4 67.16(12) 2_677 . ? O10 Ca1 O4 125.96(12) . . ? O3 Ca1 O4 49.52(9) . . ? O8 Ca1 O4 122.26(10) . . ? O11 Ca1 C11 84.87(16) . . ? O12 Ca1 C11 162.77(12) . . ? O9 Ca1 C11 78.07(12) . . ? O4 Ca1 C11 90.61(11) 2_677 . ? O10 Ca1 C11 114.92(13) . . ? O3 Ca1 C11 25.05(10) . . ? O8 Ca1 C11 99.31(11) . . ? O4 Ca1 C11 24.48(10) . . ? O11 Ca1 Ca1 69.73(10) . 2_677 ? O12 Ca1 Ca1 117.13(9) . 2_677 ? O9 Ca1 Ca1 72.83(8) . 2_677 ? O4 Ca1 Ca1 35.68(8) 2_677 2_677 ? O10 Ca1 Ca1 139.19(9) . 2_677 ? O3 Ca1 Ca1 80.02(7) . 2_677 ? O8 Ca1 Ca1 142.52(8) . 2_677 ? O4 Ca1 Ca1 31.48(6) . 2_677 ? C11 Ca1 Ca1 55.25(8) . 2_677 ? O11 Ca1 H8D 127.6 . . ? O12 Ca1 H8D 70.2 . . ? O9 Ca1 H8D 90.2 . . ? O4 Ca1 H8D 148.5 2_677 . ? O10 Ca1 H8D 57.9 . . ? O3 Ca1 H8D 87.1 . . ? O8 Ca1 H8D 17.5 . . ? O4 Ca1 H8D 136.2 . . ? C11 Ca1 H8D 112.0 . . ? Ca1 Ca1 H8D 160.1 2_677 . ? O11 Ca1 H11B 16.7 . . ? O12 Ca1 H11B 112.0 . . ? O9 Ca1 H11B 125.5 . . ? O4 Ca1 H11B 60.2 2_677 . ? O10 Ca1 H11B 86.6 . . ? O3 Ca1 H11B 94.9 . . ? O8 Ca1 H11B 156.2 . . ? O4 Ca1 H11B 59.8 . . ? C11 Ca1 H11B 76.7 . . ? Ca1 Ca1 H11B 53.1 2_677 . ? H8D Ca1 H11B 144.1 . . ? O11 Ca1 H11A 16.9 . . ? O12 Ca1 H11A 118.4 . . ? O9 Ca1 H11A 148.5 . . ? O4 Ca1 H11A 89.0 2_677 . ? O10 Ca1 H11A 62.0 . . ? O3 Ca1 H11A 84.5 . . ? O8 Ca1 H11A 127.3 . . ? O4 Ca1 H11A 70.8 . . ? C11 Ca1 H11A 76.7 . . ? Ca1 Ca1 H11A 77.4 2_677 . ? H8D Ca1 H11A 116.7 . . ? H11B Ca1 H11A 28.9 . . ? Ca1 O8 H8D 100.1 . . ? Ca1 O8 H8C 105.8 . . ? H8D O8 H8C 109.4 . . ? Ca1 O9 H9A 121.8 . . ? Ca1 O9 H9B 120.1 . . ? H9A O9 H9B 110.5 . . ? Ca1 O10 H10C 115.1 . . ? Ca1 O10 H10D 120.2 . . ? H10C O10 H10D 109.6 . . ? Ca1 O11 H11B 109.8 . . ? Ca1 O11 H11A 108.8 . . ? H11B O11 H11A 109.5 . . ? Ca1 O12 H12A 109.3 . . ? Ca1 O12 H12B 109.2 . . ? H12A O12 H12B 109.5 . . ? H1W1 O1W H1W2 109.5 . . ? H2W1 O2W H2W2 109.5 . . ? 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 O2W H2W2 O8 0.89 2.49 3.016(9) 118 2_666 O2W H2W1 O1W 0.89 2.12 2.837(18) 138 . O1W H1W2 O6 0.89 2.46 2.820(9) 105 1_455 O1W H1W1 O1W 0.89 2.39 2.94(2) 120 2_565 O12 H12B O1W 0.89 2.15 2.965(9) 151 2_666 O12 H12A O5 0.89 1.97 2.764(5) 147 1_556 O11 H11B O9 0.85 1.95 2.782(5) 167 2_677 O10 H10D O5 0.85 2.11 2.946(5) 168 2_666 O10 H10C O2 0.85 1.87 2.714(4) 170 1_545 O9 H9B O7 0.85 1.94 2.790(5) 177 1_556 O9 H9A O7 0.84 1.97 2.784(4) 163 2_776 O8 H8D O2 0.85 1.93 2.716(5) 154 1_545 O8 H8C O1 0.85 1.89 2.732(4) 171 . O8 H8D O10 0.85 2.54 2.958(5) 112 . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.860 _refine_diff_density_min -0.604 _refine_diff_density_rms 0.105 ####################################################################### # # 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_compound_2 _database_code_depnum_ccdc_archive 'CCDC 931663' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 Cu N2 O9 S Sr' _chemical_formula_sum 'C11 H12 Cu N2 O9 S Sr' _chemical_formula_weight 499.45 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' Sr Sr -1.5307 3.2498 '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 _symmetry_space_group_name_Hall '-P 2ybc' 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 8.1109(11) _cell_length_b 11.7065(18) _cell_length_c 16.460(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.757(9) _cell_angle_gamma 90.00 _cell_volume 1535.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3277 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 23.96 _exptl_crystal_description Block _exptl_crystal_colour 'violet red ' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 988 _exptl_absorpt_coefficient_mu 5.048 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.268 _exptl_absorpt_correction_T_max 0.359 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 Smart Aepex CCD' _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 17039 _diffrn_reflns_av_R_equivalents 0.0747 _diffrn_reflns_av_sigmaI/netI 0.1328 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3016 _reflns_number_gt 1934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0379P)^2^+6.8000P] 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 3016 _refine_ls_number_parameters 226 _refine_ls_number_restraints 207 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.33105(10) 0.41311(7) 0.45665(5) 0.0288(2) Uani 1 1 d U . . Sr1 Sr 0.35140(8) 0.08282(6) 0.58536(4) 0.02622(19) Uani 1 1 d U . . C1 C 0.1772(8) 0.5507(5) 0.5623(4) 0.0255(5) Uani 1 1 d U . . C2 C 0.1161(8) 0.5716(6) 0.6385(4) 0.0253(6) Uani 1 1 d U . . H2 H 0.1230 0.5132 0.6773 0.030 Uiso 1 1 calc R . . C3 C 0.0489(8) 0.6743(6) 0.6552(4) 0.0253(6) Uani 1 1 d U . . H3 H 0.0099 0.6836 0.7045 0.030 Uiso 1 1 calc R . . C4 C 0.0382(8) 0.7623(6) 0.6012(4) 0.0248(6) Uani 1 1 d U . . C5 C 0.0938(8) 0.7515(6) 0.5251(4) 0.0252(6) Uani 1 1 d U . . H5 H 0.0854 0.8126 0.4885 0.030 Uiso 1 1 calc R . . C6 C 0.1620(8) 0.6469(6) 0.5058(4) 0.0254(5) Uani 1 1 d U . . C7 C 0.2183(8) 0.6394(6) 0.4293(4) 0.0258(5) Uani 1 1 d U . . H7 H 0.1967 0.7023 0.3945 0.031 Uiso 1 1 calc R . . C8 C 0.3527(8) 0.5652(6) 0.3242(4) 0.0269(5) Uani 1 1 d U . . H8A H 0.4416 0.6215 0.3282 0.032 Uiso 1 1 calc R . . H8B H 0.2616 0.5887 0.2805 0.032 Uiso 1 1 calc R . . C9 C 0.4182(8) 0.4490(6) 0.3036(4) 0.0273(5) Uani 1 1 d U . . C10 C 0.4788(8) 0.2595(6) 0.3575(4) 0.0270(5) Uani 1 1 d U . . H10A H 0.5930 0.2624 0.3477 0.032 Uiso 1 1 calc R . . H10B H 0.4115 0.2170 0.3126 0.032 Uiso 1 1 calc R . . C11 C 0.4759(8) 0.1987(6) 0.4396(4) 0.0265(5) Uani 1 1 d U . . N1 N 0.2926(7) 0.5588(5) 0.4036(3) 0.0267(5) Uani 1 1 d U . . N2 N 0.4118(7) 0.3772(5) 0.3595(3) 0.0272(5) Uani 1 1 d U . . S1 S -0.0284(2) 0.90197(14) 0.62642(10) 0.0273(3) Uani 1 1 d U . . O5 O -0.1510(5) 0.9415(4) 0.5547(3) 0.0277(6) Uani 1 1 d U . . O6 O 0.1208(5) 0.9750(4) 0.6386(3) 0.0274(6) Uani 1 1 d U . . O7 O -0.0994(5) 0.8882(4) 0.7003(3) 0.0286(7) Uani 1 1 d U . . O1 O 0.2425(5) 0.4524(4) 0.5503(3) 0.0255(6) Uani 1 1 d U . . O2 O 0.4673(5) 0.4392(4) 0.2366(3) 0.0275(6) Uani 1 1 d U . . O3 O 0.4011(5) 0.2581(4) 0.4911(3) 0.0265(6) Uani 1 1 d U . . O4 O 0.5287(5) 0.1043(4) 0.4521(3) 0.0269(6) Uani 1 1 d U . . O8 O 0.6718(5) 0.1136(4) 0.6390(3) 0.0259(9) Uani 1 1 d U . . H8D H 0.7141 0.1246 0.5962 0.031 Uiso 1 1 d R . . H8E H 0.7101 0.0499 0.6590 0.031 Uiso 1 1 d R . . O9 O 0.2210(5) 0.2610(4) 0.6438(3) 0.0245(9) Uani 1 1 d U . . H9Y H 0.2966 0.3114 0.6575 0.029 Uiso 1 1 d R . . H9X H 0.1436 0.2878 0.6067 0.029 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 0.0305(5) 0.0305(4) 0.0275(5) 0.0018(4) 0.0107(3) 0.0048(4) Sr1 0.0242(3) 0.0294(4) 0.0253(3) 0.0015(3) 0.0054(3) 0.0021(3) C1 0.0275(12) 0.0253(10) 0.0250(11) 0.0023(9) 0.0085(9) 0.0022(9) C2 0.0275(13) 0.0253(11) 0.0243(12) 0.0028(10) 0.0075(10) 0.0027(10) C3 0.0279(13) 0.0251(10) 0.0240(13) 0.0016(10) 0.0078(11) 0.0021(11) C4 0.0281(13) 0.0238(10) 0.0237(13) 0.0002(10) 0.0081(11) 0.0022(10) C5 0.0281(13) 0.0252(10) 0.0240(12) 0.0014(10) 0.0087(10) 0.0020(10) C6 0.0274(11) 0.0257(9) 0.0248(11) 0.0019(9) 0.0092(9) 0.0021(9) C7 0.0279(12) 0.0267(10) 0.0247(11) 0.0021(9) 0.0096(10) 0.0025(10) C8 0.0300(12) 0.0270(10) 0.0260(11) 0.0002(9) 0.0107(10) 0.0032(10) C9 0.0304(12) 0.0272(10) 0.0260(10) -0.0001(8) 0.0092(9) 0.0038(10) C10 0.0312(13) 0.0267(10) 0.0251(11) -0.0007(8) 0.0104(10) 0.0027(10) C11 0.0310(13) 0.0259(10) 0.0246(10) -0.0011(8) 0.0102(9) 0.0036(10) N1 0.0292(12) 0.0278(9) 0.0253(11) 0.0007(8) 0.0103(10) 0.0026(10) N2 0.0305(12) 0.0266(10) 0.0258(10) -0.0005(8) 0.0093(9) 0.0028(10) S1 0.0323(8) 0.0216(7) 0.0286(8) -0.0025(6) 0.0068(6) 0.0014(6) O5 0.0320(11) 0.0213(11) 0.0297(11) -0.0044(10) 0.0050(9) 0.0030(10) O6 0.0318(11) 0.0225(10) 0.0286(12) -0.0024(10) 0.0073(10) 0.0001(9) O7 0.0314(16) 0.0244(16) 0.0321(13) -0.0043(13) 0.0117(12) 0.0039(13) O1 0.0273(14) 0.0254(11) 0.0253(12) 0.0026(10) 0.0087(10) 0.0030(11) O2 0.0307(13) 0.0273(13) 0.0261(12) 0.0012(11) 0.0092(11) 0.0050(12) O3 0.0310(14) 0.0271(10) 0.0235(12) -0.0007(8) 0.0105(10) 0.0043(10) O4 0.0316(14) 0.0254(11) 0.0259(12) -0.0013(10) 0.0106(9) 0.0040(11) O8 0.0251(11) 0.028(2) 0.0257(17) 0.0021(17) 0.0074(15) 0.0006(15) O9 0.028(2) 0.0288(19) 0.018(2) 0.0080(17) 0.0074(16) 0.0050(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 O1 1.876(4) . ? Cu1 N2 1.885(5) . ? Cu1 N1 1.915(5) . ? Cu1 O3 1.954(4) . ? Sr1 O2 2.504(4) 4_566 ? Sr1 O4 2.520(4) 3_656 ? Sr1 O6 2.543(5) 1_545 ? Sr1 O5 2.576(4) 3_566 ? Sr1 O9 2.602(4) . ? Sr1 O8 2.609(4) . ? Sr1 O3 2.648(4) . ? Sr1 O4 2.850(4) . ? Sr1 C11 3.086(7) . ? Sr1 H8D 2.9546 . ? Sr1 H8E 2.9612 . ? C1 O1 1.297(8) . ? C1 C2 1.453(9) . ? C1 C6 1.451(9) . ? C2 C3 1.369(9) . ? C2 H2 0.9300 . ? C3 C4 1.354(9) . ? C3 H3 0.9300 . ? C4 C5 1.414(9) . ? C4 S1 1.794(7) . ? C5 C6 1.404(9) . ? C5 H5 0.9300 . ? C6 C7 1.421(9) . ? C7 N1 1.235(8) . ? C7 H7 0.9300 . ? C8 N1 1.480(8) . ? C8 C9 1.521(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O2 1.247(8) . ? C9 N2 1.255(8) . ? C10 N2 1.484(8) . ? C10 C11 1.531(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O4 1.189(8) . ? C11 O3 1.328(7) . ? S1 O7 1.448(5) . ? S1 O6 1.465(5) . ? S1 O5 1.469(5) . ? O5 Sr1 2.577(4) 3_566 ? O6 Sr1 2.543(5) 1_565 ? O2 Sr1 2.504(4) 4_565 ? O4 Sr1 2.520(4) 3_656 ? O8 H8D 0.8500 . ? O8 H8E 0.8500 . ? O9 H9Y 0.8500 . ? O9 H9X 0.8500 . ? 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 N2 177.4(2) . . ? O1 Cu1 N1 95.8(2) . . ? N2 Cu1 N1 82.2(2) . . ? O1 Cu1 O3 97.13(18) . . ? N2 Cu1 O3 84.9(2) . . ? N1 Cu1 O3 166.8(2) . . ? O2 Sr1 O4 93.62(14) 4_566 3_656 ? O2 Sr1 O6 76.73(14) 4_566 1_545 ? O4 Sr1 O6 89.72(14) 3_656 1_545 ? O2 Sr1 O5 159.22(14) 4_566 3_566 ? O4 Sr1 O5 83.85(14) 3_656 3_566 ? O6 Sr1 O5 82.63(14) 1_545 3_566 ? O2 Sr1 O9 79.52(14) 4_566 . ? O4 Sr1 O9 171.56(14) 3_656 . ? O6 Sr1 O9 83.95(14) 1_545 . ? O5 Sr1 O9 100.80(13) 3_566 . ? O2 Sr1 O8 60.80(14) 4_566 . ? O4 Sr1 O8 78.31(14) 3_656 . ? O6 Sr1 O8 134.58(14) 1_545 . ? O5 Sr1 O8 137.76(14) 3_566 . ? O9 Sr1 O8 102.23(14) . . ? O2 Sr1 O3 126.29(14) 4_566 . ? O4 Sr1 O3 114.99(14) 3_656 . ? O6 Sr1 O3 142.03(14) 1_545 . ? O5 Sr1 O3 72.61(14) 3_566 . ? O9 Sr1 O3 73.28(13) . . ? O8 Sr1 O3 80.81(13) . . ? O2 Sr1 O4 128.64(14) 4_566 . ? O4 Sr1 O4 67.37(16) 3_656 . ? O6 Sr1 O4 144.89(13) 1_545 . ? O5 Sr1 O4 69.25(13) 3_566 . ? O9 Sr1 O4 120.80(13) . . ? O8 Sr1 O4 68.57(13) . . ? O3 Sr1 O4 47.69(13) . . ? O2 Sr1 C11 134.53(16) 4_566 . ? O4 Sr1 C11 89.70(16) 3_656 . ? O6 Sr1 C11 148.69(16) 1_545 . ? O5 Sr1 C11 66.19(16) 3_566 . ? O9 Sr1 C11 98.60(15) . . ? O8 Sr1 C11 75.68(16) . . ? O3 Sr1 C11 25.33(15) . . ? O4 Sr1 C11 22.67(14) . . ? O2 Sr1 Sr1 115.69(10) 4_566 3_656 ? O4 Sr1 Sr1 36.03(10) 3_656 3_656 ? O6 Sr1 Sr1 121.24(10) 1_545 3_656 ? O5 Sr1 Sr1 73.37(10) 3_566 3_656 ? O9 Sr1 Sr1 152.09(10) . 3_656 ? O8 Sr1 Sr1 69.69(10) . 3_656 ? O3 Sr1 Sr1 78.99(9) . 3_656 ? O4 Sr1 Sr1 31.34(9) . 3_656 ? C11 Sr1 Sr1 53.77(12) . 3_656 ? O2 Sr1 H8D 76.8 4_566 . ? O4 Sr1 H8D 74.5 3_656 . ? O6 Sr1 H8D 148.1 1_545 . ? O5 Sr1 H8D 121.8 3_566 . ? O9 Sr1 H8D 108.3 . . ? O8 Sr1 H8D 16.1 . . ? O3 Sr1 H8D 69.4 . . ? O4 Sr1 H8D 52.5 . . ? C11 Sr1 H8D 60.5 . . ? Sr1 Sr1 H8D 57.5 3_656 . ? O2 Sr1 H8E 54.7 4_566 . ? O4 Sr1 H8E 65.9 3_656 . ? O6 Sr1 H8E 121.6 1_545 . ? O5 Sr1 H8E 139.4 3_566 . ? O9 Sr1 H8E 112.9 . . ? O8 Sr1 H8E 16.0 . . ? O3 Sr1 H8E 95.5 . . ? O4 Sr1 H8E 74.2 . . ? C11 Sr1 H8E 86.4 . . ? Sr1 Sr1 H8E 66.2 3_656 . ? H8D Sr1 H8E 26.6 . . ? O1 C1 C2 119.7(6) . . ? O1 C1 C6 125.4(6) . . ? C2 C1 C6 114.9(6) . . ? C3 C2 C1 122.3(6) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C4 C3 C2 121.1(6) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 121.4(6) . . ? C3 C4 S1 121.8(5) . . ? C5 C4 S1 116.5(5) . . ? C6 C5 C4 118.8(6) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C7 117.4(6) . . ? C5 C6 C1 121.5(6) . . ? C7 C6 C1 121.1(6) . . ? N1 C7 C6 127.5(6) . . ? N1 C7 H7 116.3 . . ? C6 C7 H7 116.3 . . ? N1 C8 C9 109.8(5) . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O2 C9 N2 130.6(6) . . ? O2 C9 C8 117.5(6) . . ? N2 C9 C8 111.8(6) . . ? N2 C10 C11 110.2(5) . . ? N2 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? N2 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O4 C11 O3 124.7(6) . . ? O4 C11 C10 121.3(6) . . ? O3 C11 C10 113.9(5) . . ? O4 C11 Sr1 67.5(4) . . ? O3 C11 Sr1 58.6(3) . . ? C10 C11 Sr1 162.1(4) . . ? C7 N1 C8 121.7(6) . . ? C7 N1 Cu1 124.9(5) . . ? C8 N1 Cu1 113.3(4) . . ? C9 N2 C10 122.8(6) . . ? C9 N2 Cu1 122.7(5) . . ? C10 N2 Cu1 114.4(4) . . ? O7 S1 O6 113.4(3) . . ? O7 S1 O5 113.2(3) . . ? O6 S1 O5 110.1(3) . . ? O7 S1 C4 106.1(3) . . ? O6 S1 C4 106.7(3) . . ? O5 S1 C4 106.8(3) . . ? S1 O5 Sr1 154.6(3) . 3_566 ? S1 O6 Sr1 152.2(3) . 1_565 ? C1 O1 Cu1 124.9(4) . . ? C9 O2 Sr1 140.0(4) . 4_565 ? C11 O3 Cu1 116.3(4) . . ? C11 O3 Sr1 96.1(4) . . ? Cu1 O3 Sr1 145.3(2) . . ? C11 O4 Sr1 155.3(4) . 3_656 ? C11 O4 Sr1 89.9(4) . . ? Sr1 O4 Sr1 112.63(16) 3_656 . ? Sr1 O8 H8D 105.7 . . ? Sr1 O8 H8E 106.2 . . ? H8D O8 H8E 106.3 . . ? Sr1 O9 H9Y 109.3 . . ? Sr1 O9 H9X 109.1 . . ? H9Y O9 H9X 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 178.8(6) . . . . ? C6 C1 C2 C3 0.3(9) . . . . ? C1 C2 C3 C4 -0.9(10) . . . . ? C2 C3 C4 C5 0.8(10) . . . . ? C2 C3 C4 S1 -173.2(5) . . . . ? C3 C4 C5 C6 -0.2(10) . . . . ? S1 C4 C5 C6 174.1(5) . . . . ? C4 C5 C6 C7 -179.3(6) . . . . ? C4 C5 C6 C1 -0.4(10) . . . . ? O1 C1 C6 C5 -178.1(6) . . . . ? C2 C1 C6 C5 0.3(9) . . . . ? O1 C1 C6 C7 0.9(10) . . . . ? C2 C1 C6 C7 179.3(6) . . . . ? C5 C6 C7 N1 174.2(7) . . . . ? C1 C6 C7 N1 -4.7(11) . . . . ? N1 C8 C9 O2 177.2(6) . . . . ? N1 C8 C9 N2 -2.5(8) . . . . ? N2 C10 C11 O4 -177.9(6) . . . . ? N2 C10 C11 O3 6.1(8) . . . . ? N2 C10 C11 Sr1 67.1(16) . . . . ? O2 Sr1 C11 O4 85.2(4) 4_566 . . . ? O4 Sr1 C11 O4 -9.5(4) 3_656 . . . ? O6 Sr1 C11 O4 -98.5(5) 1_545 . . . ? O5 Sr1 C11 O4 -92.9(4) 3_566 . . . ? O9 Sr1 C11 O4 169.0(4) . . . . ? O8 Sr1 C11 O4 68.5(4) . . . . ? O3 Sr1 C11 O4 167.3(7) . . . . ? Sr1 Sr1 C11 O4 -6.6(3) 3_656 . . . ? O2 Sr1 C11 O3 -82.1(4) 4_566 . . . ? O4 Sr1 C11 O3 -176.9(4) 3_656 . . . ? O6 Sr1 C11 O3 94.1(4) 1_545 . . . ? O5 Sr1 C11 O3 99.7(4) 3_566 . . . ? O9 Sr1 C11 O3 1.6(4) . . . . ? O8 Sr1 C11 O3 -98.9(4) . . . . ? O4 Sr1 C11 O3 -167.3(7) . . . . ? Sr1 Sr1 C11 O3 -174.0(4) 3_656 . . . ? O2 Sr1 C11 C10 -151.7(13) 4_566 . . . ? O4 Sr1 C11 C10 113.5(14) 3_656 . . . ? O6 Sr1 C11 C10 24.5(16) 1_545 . . . ? O5 Sr1 C11 C10 30.1(14) 3_566 . . . ? O9 Sr1 C11 C10 -68.0(14) . . . . ? O8 Sr1 C11 C10 -168.5(14) . . . . ? O3 Sr1 C11 C10 -69.7(14) . . . . ? O4 Sr1 C11 C10 123.0(16) . . . . ? Sr1 Sr1 C11 C10 116.4(15) 3_656 . . . ? C6 C7 N1 C8 -176.4(6) . . . . ? C6 C7 N1 Cu1 7.2(10) . . . . ? C9 C8 N1 C7 -172.6(6) . . . . ? C9 C8 N1 Cu1 4.2(6) . . . . ? O1 Cu1 N1 C7 -5.1(6) . . . . ? N2 Cu1 N1 C7 173.2(6) . . . . ? O3 Cu1 N1 C7 -173.5(7) . . . . ? O1 Cu1 N1 C8 178.3(4) . . . . ? N2 Cu1 N1 C8 -3.5(4) . . . . ? O3 Cu1 N1 C8 9.9(12) . . . . ? O2 C9 N2 C10 4.7(12) . . . . ? C8 C9 N2 C10 -175.7(6) . . . . ? O2 C9 N2 Cu1 -180.0(6) . . . . ? C8 C9 N2 Cu1 -0.3(8) . . . . ? C11 C10 N2 C9 171.7(6) . . . . ? C11 C10 N2 Cu1 -4.0(7) . . . . ? N1 Cu1 N2 C9 2.3(6) . . . . ? O3 Cu1 N2 C9 -174.7(6) . . . . ? N1 Cu1 N2 C10 178.0(5) . . . . ? O3 Cu1 N2 C10 1.0(4) . . . . ? C3 C4 S1 O7 -13.1(6) . . . . ? C5 C4 S1 O7 172.6(5) . . . . ? C3 C4 S1 O6 108.2(6) . . . . ? C5 C4 S1 O6 -66.1(6) . . . . ? C3 C4 S1 O5 -134.1(6) . . . . ? C5 C4 S1 O5 51.6(6) . . . . ? O7 S1 O5 Sr1 -104.7(6) . . . 3_566 ? O6 S1 O5 Sr1 127.2(6) . . . 3_566 ? C4 S1 O5 Sr1 11.7(7) . . . 3_566 ? O7 S1 O6 Sr1 -173.7(5) . . . 1_565 ? O5 S1 O6 Sr1 -45.7(6) . . . 1_565 ? C4 S1 O6 Sr1 69.8(6) . . . 1_565 ? C2 C1 O1 Cu1 -178.6(4) . . . . ? C6 C1 O1 Cu1 -0.3(9) . . . . ? N1 Cu1 O1 C1 1.7(5) . . . . ? O3 Cu1 O1 C1 179.1(5) . . . . ? N2 C9 O2 Sr1 102.0(8) . . . 4_565 ? C8 C9 O2 Sr1 -77.6(8) . . . 4_565 ? O4 C11 O3 Cu1 178.6(5) . . . . ? C10 C11 O3 Cu1 -5.6(7) . . . . ? Sr1 C11 O3 Cu1 -167.2(4) . . . . ? O4 C11 O3 Sr1 -14.3(7) . . . . ? C10 C11 O3 Sr1 161.6(5) . . . . ? O1 Cu1 O3 C11 -179.0(4) . . . . ? N2 Cu1 O3 C11 2.7(5) . . . . ? N1 Cu1 O3 C11 -10.6(11) . . . . ? O1 Cu1 O3 Sr1 23.8(4) . . . . ? N2 Cu1 O3 Sr1 -154.5(4) . . . . ? N1 Cu1 O3 Sr1 -167.8(7) . . . . ? O2 Sr1 O3 C11 118.8(4) 4_566 . . . ? O4 Sr1 O3 C11 3.4(4) 3_656 . . . ? O6 Sr1 O3 C11 -122.6(4) 1_545 . . . ? O5 Sr1 O3 C11 -70.9(4) 3_566 . . . ? O9 Sr1 O3 C11 -178.3(4) . . . . ? O8 Sr1 O3 C11 75.9(4) . . . . ? O4 Sr1 O3 C11 6.6(3) . . . . ? Sr1 Sr1 O3 C11 4.9(3) 3_656 . . . ? O2 Sr1 O3 Cu1 -81.6(4) 4_566 . . . ? O4 Sr1 O3 Cu1 163.0(3) 3_656 . . . ? O6 Sr1 O3 Cu1 37.0(5) 1_545 . . . ? O5 Sr1 O3 Cu1 88.7(4) 3_566 . . . ? O9 Sr1 O3 Cu1 -18.7(3) . . . . ? O8 Sr1 O3 Cu1 -124.5(4) . . . . ? O4 Sr1 O3 Cu1 166.1(5) . . . . ? C11 Sr1 O3 Cu1 159.6(6) . . . . ? Sr1 Sr1 O3 Cu1 164.5(4) 3_656 . . . ? O3 C11 O4 Sr1 169.7(6) . . . 3_656 ? C10 C11 O4 Sr1 -5.8(15) . . . 3_656 ? Sr1 C11 O4 Sr1 156.6(11) . . . 3_656 ? O3 C11 O4 Sr1 13.1(7) . . . . ? C10 C11 O4 Sr1 -162.4(6) . . . . ? O2 Sr1 O4 C11 -114.6(4) 4_566 . . . ? O4 Sr1 O4 C11 169.7(5) 3_656 . . . ? O6 Sr1 O4 C11 116.7(4) 1_545 . . . ? O5 Sr1 O4 C11 77.7(4) 3_566 . . . ? O9 Sr1 O4 C11 -12.7(4) . . . . ? O8 Sr1 O4 C11 -104.5(4) . . . . ? O3 Sr1 O4 C11 -7.3(4) . . . . ? Sr1 Sr1 O4 C11 169.7(5) 3_656 . . . ? O2 Sr1 O4 Sr1 75.8(2) 4_566 . . 3_656 ? O4 Sr1 O4 Sr1 0.0 3_656 . . 3_656 ? O6 Sr1 O4 Sr1 -53.0(3) 1_545 . . 3_656 ? O5 Sr1 O4 Sr1 -91.94(18) 3_566 . . 3_656 ? O9 Sr1 O4 Sr1 177.63(15) . . . 3_656 ? O8 Sr1 O4 Sr1 85.86(18) . . . 3_656 ? O3 Sr1 O4 Sr1 -176.9(3) . . . 3_656 ? C11 Sr1 O4 Sr1 -169.7(5) . . . 3_656 ? 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 O8 H8D O4 0.85 2.58 3.085(5) 120 . O8 H8D O5 0.85 2.56 2.965(5) 111 1_645 O8 H8E O7 0.85 2.45 3.272(5) 162 1_645 O8 H8D O5 0.85 2.56 2.965(5) 111 1_645 O8 H8E S1 0.85 2.87 3.505(4) 134 1_645 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.829 _refine_diff_density_min -0.817 _refine_diff_density_rms 0.143 ####################################################################### # # 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_compound_3 _database_code_depnum_ccdc_archive 'CCDC 931664' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H16 Ba Cu N2 O11 S' _chemical_formula_sum 'C11 H16 Ba Cu N2 O11 S' _chemical_formula_weight 585.20 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' Ba Ba -0.3244 2.2819 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.498(2) _cell_length_b 9.691(3) _cell_length_c 12.530(3) _cell_angle_alpha 110.582(4) _cell_angle_beta 91.961(4) _cell_angle_gamma 113.516(4) _cell_volume 867.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3098 _cell_measurement_theta_min 2.507 _cell_measurement_theta_max 27.947 _exptl_crystal_description Block _exptl_crystal_colour 'violet red ' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 570 _exptl_absorpt_coefficient_mu 3.666 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.211 _exptl_absorpt_correction_T_max 0.258 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 Smart Aepex CCD' _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 4310 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2989 _reflns_number_gt 2763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0593P)^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 2989 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Ba1 Ba 1.37514(3) 1.11884(3) 0.40657(2) 0.02395(13) Uani 1 1 d . . . Cu1 Cu 0.95088(7) 0.58193(7) 0.17578(5) 0.02557(17) Uani 1 1 d . . . C1 C 0.7788(6) 0.6519(6) 0.0176(4) 0.0263(10) Uani 1 1 d . . . C2 C 0.7474(7) 0.7669(6) -0.0118(4) 0.0316(11) Uani 1 1 d . . . H2 H 0.8070 0.8776 0.0370 0.038 Uiso 1 1 calc R . . C3 C 0.6319(6) 0.7204(6) -0.1098(5) 0.0307(11) Uani 1 1 d . . . H3 H 0.6111 0.7990 -0.1259 0.037 Uiso 1 1 calc R . . C4 C 0.5448(6) 0.5566(6) -0.1860(4) 0.0236(10) Uani 1 1 d . . . C5 C 0.5692(6) 0.4411(6) -0.1572(4) 0.0250(10) Uani 1 1 d . . . H5 H 0.5067 0.3308 -0.2063 0.030 Uiso 1 1 calc R . . C6 C 0.6843(6) 0.4842(6) -0.0570(4) 0.0231(10) Uani 1 1 d . . . C7 C 0.6972(6) 0.3521(6) -0.0343(4) 0.0274(11) Uani 1 1 d . . . H7 H 0.6295 0.2451 -0.0880 0.033 Uiso 1 1 calc R . . C8 C 0.7958(7) 0.2348(6) 0.0777(4) 0.0301(11) Uani 1 1 d . . . H8A H 0.8311 0.1688 0.0144 0.036 Uiso 1 1 calc R . . H8B H 0.6785 0.1662 0.0823 0.036 Uiso 1 1 calc R . . C9 C 0.9216(6) 0.2982(6) 0.1914(4) 0.0260(10) Uani 1 1 d . . . C10 C 1.1335(6) 0.5476(6) 0.3482(4) 0.0272(10) Uani 1 1 d . . . H10A H 1.2225 0.5088 0.3486 0.033 Uiso 1 1 calc R . . H10B H 1.0721 0.5339 0.4103 0.033 Uiso 1 1 calc R . . C11 C 1.2177(6) 0.7261(6) 0.3668(4) 0.0253(10) Uani 1 1 d . . . N1 N 0.7959(5) 0.3735(5) 0.0549(3) 0.0261(9) Uani 1 1 d . . . N2 N 1.0125(5) 0.4554(5) 0.2381(3) 0.0254(9) Uani 1 1 d . . . O1 O 0.8958(5) 0.7077(4) 0.1113(3) 0.0340(9) Uani 1 1 d . . . O2 O 0.9257(5) 0.1958(4) 0.2307(3) 0.0367(9) Uani 1 1 d . . . O3 O 1.1498(4) 0.7700(4) 0.2986(3) 0.0322(8) Uani 1 1 d . . . O4 O 1.3458(5) 0.8273(4) 0.4455(3) 0.0371(9) Uani 1 1 d . . . O5 O 0.4789(4) 0.4152(4) -0.4103(3) 0.0326(8) Uani 1 1 d . . . O6 O 0.2326(4) 0.3916(4) -0.3191(3) 0.0298(8) Uani 1 1 d . . . O7 O 0.4240(5) 0.6527(4) -0.3220(3) 0.0354(8) Uani 1 1 d . . . O8 O 1.0847(5) 1.2111(5) 0.4311(3) 0.0407(9) Uani 1 1 d . . . H8C H 1.0731 1.2456 0.3790 0.061 Uiso 1 1 d R . . H8D H 1.1069 1.2866 0.4980 0.061 Uiso 1 1 d R . . O9 O 1.2077(5) 1.0736(4) 0.5913(3) 0.0392(9) Uani 1 1 d . . . H9A H 1.2165 1.1653 0.6390 0.059 Uiso 1 1 d R . . H9B H 1.1000 1.0068 0.5642 0.059 Uiso 1 1 d R . . O10 O 1.5904(5) 1.0048(4) 0.2748(3) 0.0391(9) Uani 1 1 d . . . H10C H 1.6643 0.9997 0.3189 0.059 Uiso 1 1 d R . . H10D H 1.6444 1.0706 0.2437 0.059 Uiso 1 1 d R . . O11 O 1.1429(5) 1.0189(5) 0.2030(4) 0.0427(10) Uani 1 1 d . . . H11A H 1.0403 0.9582 0.2069 0.064 Uiso 1 1 d R . . H11B H 1.1437 1.1028 0.1952 0.064 Uiso 1 1 d R . . S1 S 0.41095(15) 0.50149(14) -0.31860(10) 0.0235(3) 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 Ba1 0.02258(19) 0.01973(18) 0.02356(19) 0.00487(13) -0.00399(12) 0.00755(13) Cu1 0.0255(3) 0.0168(3) 0.0268(3) 0.0055(2) -0.0078(2) 0.0059(3) C1 0.025(2) 0.023(2) 0.024(3) 0.006(2) -0.002(2) 0.007(2) C2 0.033(3) 0.017(2) 0.029(3) 0.006(2) -0.009(2) 0.001(2) C3 0.030(3) 0.020(2) 0.036(3) 0.008(2) -0.005(2) 0.009(2) C4 0.023(2) 0.023(2) 0.018(2) 0.0055(19) 0.0000(19) 0.008(2) C5 0.023(2) 0.019(2) 0.026(2) 0.004(2) 0.001(2) 0.006(2) C6 0.024(2) 0.023(2) 0.020(2) 0.0061(19) 0.0017(19) 0.011(2) C7 0.029(3) 0.019(2) 0.024(2) 0.0022(19) -0.003(2) 0.008(2) C8 0.035(3) 0.018(2) 0.031(3) 0.006(2) -0.005(2) 0.010(2) C9 0.026(2) 0.019(2) 0.031(3) 0.008(2) 0.005(2) 0.011(2) C10 0.025(2) 0.025(3) 0.031(3) 0.011(2) -0.002(2) 0.011(2) C11 0.018(2) 0.024(2) 0.029(3) 0.006(2) -0.001(2) 0.010(2) N1 0.030(2) 0.017(2) 0.028(2) 0.0058(17) -0.0013(18) 0.0104(17) N2 0.021(2) 0.020(2) 0.030(2) 0.0067(17) -0.0050(17) 0.0070(17) O1 0.038(2) 0.0177(17) 0.034(2) 0.0067(15) -0.0177(16) 0.0056(15) O2 0.041(2) 0.0212(18) 0.043(2) 0.0130(16) -0.0086(17) 0.0095(16) O3 0.0264(18) 0.0206(17) 0.039(2) 0.0103(15) -0.0097(15) 0.0033(15) O4 0.033(2) 0.0238(19) 0.041(2) 0.0041(17) -0.0178(17) 0.0093(16) O5 0.0312(19) 0.041(2) 0.0200(17) 0.0048(15) 0.0019(15) 0.0166(17) O6 0.0238(18) 0.0286(19) 0.0311(19) 0.0075(15) 0.0017(15) 0.0099(15) O7 0.041(2) 0.0269(19) 0.034(2) 0.0115(16) -0.0050(16) 0.0125(17) O8 0.041(2) 0.038(2) 0.035(2) 0.0089(17) -0.0093(17) 0.0170(18) O9 0.041(2) 0.030(2) 0.047(2) 0.0138(18) 0.0065(18) 0.0159(18) O10 0.038(2) 0.037(2) 0.042(2) 0.0171(18) 0.0054(17) 0.0161(18) O11 0.038(2) 0.027(2) 0.050(3) 0.0161(18) -0.0126(18) 0.0037(17) S1 0.0234(6) 0.0215(6) 0.0215(6) 0.0055(5) -0.0017(5) 0.0092(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 Ba1 O4 2.714(3) 2_876 ? Ba1 O5 2.738(3) 1_666 ? Ba1 O7 2.774(4) 2_775 ? Ba1 O11 2.781(4) . ? Ba1 O10 2.798(4) . ? Ba1 O9 2.831(4) . ? Ba1 O3 2.893(3) . ? Ba1 O8 2.933(4) . ? Ba1 O4 2.949(4) . ? Ba1 C11 3.329(5) . ? Cu1 O1 1.865(3) . ? Cu1 N2 1.883(4) . ? Cu1 N1 1.923(4) . ? Cu1 O3 1.985(3) . ? Cu1 O6 2.430(3) 2_665 ? C1 O1 1.305(6) . ? C1 C2 1.402(7) . ? C1 C6 1.414(7) . ? C2 C3 1.361(7) . ? C2 H2 0.9300 . ? C3 C4 1.389(7) . ? C3 H3 0.9300 . ? C4 C5 1.374(7) . ? C4 S1 1.762(5) . ? C5 C6 1.390(7) . ? C5 H5 0.9300 . ? C6 C7 1.448(7) . ? C7 N1 1.276(6) . ? C7 H7 0.9300 . ? C8 N1 1.469(6) . ? C8 C9 1.518(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O2 1.265(6) . ? C9 N2 1.289(6) . ? C10 N2 1.436(6) . ? C10 C11 1.509(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O4 1.230(6) . ? C11 O3 1.289(6) . ? O4 Ba1 2.714(3) 2_876 ? O5 S1 1.452(4) . ? O5 Ba1 2.738(3) 1_444 ? O6 S1 1.462(3) . ? O6 Cu1 2.430(3) 2_665 ? O7 S1 1.441(3) . ? O7 Ba1 2.774(4) 2_775 ? O8 H8C 0.8499 . ? O8 H8D 0.8500 . ? O9 H9A 0.8500 . ? O9 H9B 0.8500 . ? O10 H10C 0.8500 . ? O10 H10D 0.8501 . ? O11 H11A 0.8500 . ? O11 H11B 0.8501 . ? 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 Ba1 O5 71.09(10) 2_876 1_666 ? O4 Ba1 O7 93.67(11) 2_876 2_775 ? O5 Ba1 O7 75.68(11) 1_666 2_775 ? O4 Ba1 O11 161.48(13) 2_876 . ? O5 Ba1 O11 123.35(11) 1_666 . ? O7 Ba1 O11 80.34(11) 2_775 . ? O4 Ba1 O10 71.52(12) 2_876 . ? O5 Ba1 O10 126.82(11) 1_666 . ? O7 Ba1 O10 70.45(11) 2_775 . ? O11 Ba1 O10 89.97(12) . . ? O4 Ba1 O9 81.29(12) 2_876 . ? O5 Ba1 O9 70.08(11) 1_666 . ? O7 Ba1 O9 145.19(11) 2_775 . ? O11 Ba1 O9 113.51(12) . . ? O10 Ba1 O9 137.35(11) . . ? O4 Ba1 O3 108.82(10) 2_876 . ? O5 Ba1 O3 149.62(11) 1_666 . ? O7 Ba1 O3 133.51(11) 2_775 . ? O11 Ba1 O3 65.37(10) . . ? O10 Ba1 O3 78.76(10) . . ? O9 Ba1 O3 79.79(11) . . ? O4 Ba1 O8 135.28(11) 2_876 . ? O5 Ba1 O8 69.88(10) 1_666 . ? O7 Ba1 O8 97.07(11) 2_775 . ? O11 Ba1 O8 63.17(12) . . ? O10 Ba1 O8 152.36(11) . . ? O9 Ba1 O8 65.55(11) . . ? O3 Ba1 O8 94.47(10) . . ? O4 Ba1 O4 65.71(12) 2_876 . ? O5 Ba1 O4 120.87(11) 1_666 . ? O7 Ba1 O4 142.87(11) 2_775 . ? O11 Ba1 O4 109.16(10) . . ? O10 Ba1 O4 73.68(11) . . ? O9 Ba1 O4 65.28(11) . . ? O3 Ba1 O4 44.05(9) . . ? O8 Ba1 O4 119.49(11) . . ? O4 Ba1 C11 86.86(11) 2_876 . ? O5 Ba1 C11 137.19(11) 1_666 . ? O7 Ba1 C11 143.86(11) 2_775 . ? O11 Ba1 C11 87.82(11) . . ? O10 Ba1 C11 75.57(11) . . ? O9 Ba1 C11 70.62(11) . . ? O3 Ba1 C11 22.54(10) . . ? O8 Ba1 C11 107.79(11) . . ? O4 Ba1 C11 21.52(11) . . ? O4 Ba1 Ba1 34.39(8) 2_876 2_876 ? O5 Ba1 Ba1 97.65(7) 1_666 2_876 ? O7 Ba1 Ba1 122.04(7) 2_775 2_876 ? O11 Ba1 Ba1 138.09(8) . 2_876 ? O10 Ba1 Ba1 69.22(8) . 2_876 ? O9 Ba1 Ba1 69.79(7) . 2_876 ? O3 Ba1 Ba1 74.85(7) . 2_876 ? O8 Ba1 Ba1 135.26(8) . 2_876 ? O4 Ba1 Ba1 31.32(7) . 2_876 ? C11 Ba1 Ba1 52.58(8) . 2_876 ? O1 Cu1 N2 178.08(18) . . ? O1 Cu1 N1 95.48(15) . . ? N2 Cu1 N1 84.52(16) . . ? O1 Cu1 O3 95.67(14) . . ? N2 Cu1 O3 84.03(15) . . ? N1 Cu1 O3 165.71(15) . . ? O1 Cu1 O6 93.97(15) . 2_665 ? N2 Cu1 O6 87.91(15) . 2_665 ? N1 Cu1 O6 101.04(15) . 2_665 ? O3 Cu1 O6 87.07(14) . 2_665 ? O1 C1 C2 117.5(4) . . ? O1 C1 C6 124.4(4) . . ? C2 C1 C6 118.0(4) . . ? C3 C2 C1 121.6(4) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 120.5(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 118.9(4) . . ? C5 C4 S1 121.4(4) . . ? C3 C4 S1 119.7(4) . . ? C4 C5 C6 122.0(4) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C6 C1 118.9(4) . . ? C5 C6 C7 117.2(4) . . ? C1 C6 C7 123.9(4) . . ? N1 C7 C6 123.9(4) . . ? N1 C7 H7 118.0 . . ? C6 C7 H7 118.0 . . ? N1 C8 C9 109.8(4) . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O2 C9 N2 127.1(5) . . ? O2 C9 C8 118.4(4) . . ? N2 C9 C8 114.4(4) . . ? N2 C10 C11 108.4(4) . . ? N2 C10 H10A 110.0 . . ? C11 C10 H10A 110.0 . . ? N2 C10 H10B 110.0 . . ? C11 C10 H10B 110.0 . . ? H10A C10 H10B 108.4 . . ? O4 C11 O3 120.9(4) . . ? O4 C11 C10 121.2(4) . . ? O3 C11 C10 117.9(4) . . ? O4 C11 Ba1 61.6(3) . . ? O3 C11 Ba1 59.3(2) . . ? C10 C11 Ba1 175.9(3) . . ? C7 N1 C8 121.8(4) . . ? C7 N1 Cu1 125.8(3) . . ? C8 N1 Cu1 112.4(3) . . ? C9 N2 C10 125.8(4) . . ? C9 N2 Cu1 118.1(3) . . ? C10 N2 Cu1 114.8(3) . . ? C1 O1 Cu1 126.3(3) . . ? C11 O3 Cu1 112.7(3) . . ? C11 O3 Ba1 98.1(3) . . ? Cu1 O3 Ba1 149.22(15) . . ? C11 O4 Ba1 146.9(3) . 2_876 ? C11 O4 Ba1 96.9(3) . . ? Ba1 O4 Ba1 114.29(12) 2_876 . ? S1 O5 Ba1 140.6(2) . 1_444 ? S1 O6 Cu1 131.1(2) . 2_665 ? S1 O7 Ba1 138.0(2) . 2_775 ? Ba1 O8 H8C 109.3 . . ? Ba1 O8 H8D 109.4 . . ? H8C O8 H8D 109.5 . . ? Ba1 O9 H9A 109.3 . . ? Ba1 O9 H9B 109.5 . . ? H9A O9 H9B 109.5 . . ? Ba1 O10 H10C 109.4 . . ? Ba1 O10 H10D 109.3 . . ? H10C O10 H10D 109.5 . . ? Ba1 O11 H11A 109.3 . . ? Ba1 O11 H11B 109.3 . . ? H11A O11 H11B 109.5 . . ? O7 S1 O5 113.3(2) . . ? O7 S1 O6 112.6(2) . . ? O5 S1 O6 110.1(2) . . ? O7 S1 C4 106.1(2) . . ? O5 S1 C4 106.5(2) . . ? O6 S1 C4 107.8(2) . . ? 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 O11 H11B O2 0.85 2.36 2.936(5) 126 1_565 O10 H10D O2 0.85 2.25 2.910(5) 135 1_665 O10 H10C O9 0.85 2.01 2.841(5) 165 2_876 O9 H9B O8 0.85 2.09 2.793(6) 140 2_776 O9 H9A S1 0.85 2.84 3.509(4) 137 1_666 O9 H9A O6 0.85 2.01 2.799(5) 153 1_666 O8 H8D S1 0.85 2.87 3.524(4) 135 1_666 O8 H8D O6 0.85 2.18 2.927(5) 147 1_666 O8 H8C O2 0.85 2.00 2.739(5) 145 1_565 O11 H11A O1 0.85 2.08 2.678(5) 127 . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.636 _refine_diff_density_min -1.134 _refine_diff_density_rms 0.160