# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Cantillo, David' 'Avalos, Martin' 'Babiano, Reyes' 'Cintas, Pedro' 'Jimenez, Jose L.' 'Light, Mark' 'Palacios, Juan C.' 'Rodriguez, Valentin' _publ_contact_author_name 'Cantillo, David' _publ_contact_author_email dcannie@unex.es _publ_section_title ; Push-pull 1,3-Thiazolium-5-thiolates as New NLO Candidates. F ormation via Concerted and Stepwise Pathways ; # Attachment '- ESI Crystallographic Data Cantillo.cif' data_Compound15 _database_code_depnum_ccdc_archive 'CCDC 784450' #TrackingRef '- ESI Crystallographic Data Cantillo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 N2 O3 S2' _chemical_formula_weight 358.42 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.5576(2) _cell_length_b 14.9916(3) _cell_length_c 20.3173(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3215.73(10) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 20111 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour Orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.350 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9334 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 21814 reflections reduced R(int) from 0.1410 to 0.0634 Ratio of minimum to maximum apparent transmission: 0.896691 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23459 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3678 _reflns_number_gt 3071 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0000P)^2^+6.2630P] 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 3678 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 C1 C 0.8263(2) 0.40739(15) 0.32264(10) 0.0184(5) Uani 1 1 d . . . C2 C 0.7127(2) 0.41871(15) 0.35565(11) 0.0200(5) Uani 1 1 d . . . H2 H 0.6430 0.4473 0.3349 0.024 Uiso 1 1 calc R . . C3 C 0.7031(2) 0.38726(16) 0.41987(11) 0.0202(5) Uani 1 1 d . . . H3 H 0.6263 0.3947 0.4436 0.024 Uiso 1 1 calc R . . C4 C 0.8060(2) 0.34477(15) 0.44967(11) 0.0189(5) Uani 1 1 d . . . C5 C 0.9200(2) 0.33622(16) 0.41510(11) 0.0221(5) Uani 1 1 d . . . H5 H 0.9905 0.3082 0.4355 0.027 Uiso 1 1 calc R . . C6 C 0.9311(2) 0.36826(16) 0.35130(11) 0.0207(5) Uani 1 1 d . . . H6 H 1.0088 0.3634 0.3279 0.025 Uiso 1 1 calc R . . C7 C 0.7942(2) 0.30038(15) 0.51427(10) 0.0178(4) Uani 1 1 d . . . C8 C 0.7236(2) 0.29172(15) 0.62145(11) 0.0185(5) Uani 1 1 d . . . C9 C 0.8309(2) 0.21406(15) 0.52724(11) 0.0193(5) Uani 1 1 d . . . C10 C 0.7134(2) 0.44008(15) 0.56940(11) 0.0218(5) Uani 1 1 d . . . H10A H 0.6290 0.4525 0.5516 0.033 Uiso 1 1 calc R . . H10B H 0.7774 0.4704 0.5425 0.033 Uiso 1 1 calc R . . H10C H 0.7184 0.4619 0.6148 0.033 Uiso 1 1 calc R . . C11 C 0.6675(2) 0.31707(15) 0.68472(11) 0.0181(4) Uani 1 1 d . . . C12 C 0.5534(2) 0.36401(16) 0.68812(11) 0.0214(5) Uani 1 1 d . . . H12 H 0.5104 0.3802 0.6488 0.026 Uiso 1 1 calc R . . C13 C 0.5028(2) 0.38694(15) 0.74851(12) 0.0209(5) Uani 1 1 d . . . H13 H 0.4255 0.4193 0.7506 0.025 Uiso 1 1 calc R . . C14 C 0.5647(2) 0.36278(16) 0.80644(11) 0.0209(5) Uani 1 1 d . . . C15 C 0.6772(2) 0.31403(16) 0.80371(11) 0.0216(5) Uani 1 1 d . . . H15 H 0.7192 0.2968 0.8431 0.026 Uiso 1 1 calc R . . C16 C 0.7270(2) 0.29110(15) 0.74288(11) 0.0197(5) Uani 1 1 d . . . H16 H 0.8029 0.2572 0.7408 0.024 Uiso 1 1 calc R . . C17 C 0.5766(3) 0.3787(2) 0.92304(12) 0.0332(6) Uani 1 1 d . . . H17A H 0.5854 0.3149 0.9323 0.050 Uiso 1 1 calc R . . H17B H 0.5309 0.4075 0.9592 0.050 Uiso 1 1 calc R . . H17C H 0.6608 0.4056 0.9187 0.050 Uiso 1 1 calc R . . N1 N 0.83397(19) 0.43352(13) 0.25304(9) 0.0205(4) Uani 1 1 d . . . N2 N 0.73687(18) 0.34278(13) 0.56835(9) 0.0181(4) Uani 1 1 d . . . O1 O 0.74149(17) 0.46994(12) 0.22768(8) 0.0284(4) Uani 1 1 d . . . O2 O 0.93179(16) 0.41597(12) 0.22297(8) 0.0257(4) Uani 1 1 d . . . O3 O 0.50754(16) 0.39064(12) 0.86291(8) 0.0269(4) Uani 1 1 d . . . S1 S 0.78452(6) 0.18780(4) 0.60751(3) 0.02106(14) Uani 1 1 d . . . S2 S 0.90335(6) 0.13470(4) 0.48028(3) 0.02378(15) 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 C1 0.0235(11) 0.0185(11) 0.0131(10) -0.0001(8) 0.0014(9) -0.0005(9) C2 0.0191(11) 0.0201(11) 0.0208(11) 0.0017(9) -0.0025(9) 0.0022(9) C3 0.0197(11) 0.0233(12) 0.0176(11) -0.0013(9) 0.0014(9) 0.0001(9) C4 0.0217(11) 0.0177(11) 0.0172(11) -0.0002(9) -0.0002(9) -0.0004(9) C5 0.0193(11) 0.0263(12) 0.0207(11) 0.0020(9) -0.0001(9) 0.0015(10) C6 0.0179(11) 0.0233(12) 0.0210(11) 0.0007(9) 0.0032(9) 0.0005(9) C7 0.0165(10) 0.0218(11) 0.0152(10) 0.0000(9) -0.0004(8) 0.0004(9) C8 0.0184(11) 0.0209(11) 0.0162(10) 0.0014(8) -0.0025(9) -0.0008(9) C9 0.0174(11) 0.0251(12) 0.0153(10) -0.0001(9) -0.0019(9) -0.0004(9) C10 0.0270(12) 0.0200(12) 0.0183(11) 0.0004(9) 0.0006(10) 0.0007(9) C11 0.0191(11) 0.0182(11) 0.0169(10) 0.0015(9) 0.0010(9) -0.0055(9) C12 0.0206(11) 0.0239(12) 0.0197(11) 0.0033(9) -0.0031(9) -0.0015(9) C13 0.0197(11) 0.0205(11) 0.0224(11) 0.0015(9) -0.0004(9) -0.0003(9) C14 0.0230(12) 0.0211(12) 0.0187(11) 0.0008(9) 0.0031(9) -0.0061(9) C15 0.0224(11) 0.0253(12) 0.0170(11) 0.0045(9) -0.0014(9) -0.0020(10) C16 0.0179(11) 0.0218(11) 0.0193(11) 0.0023(9) 0.0004(9) -0.0006(9) C17 0.0291(14) 0.0545(18) 0.0159(11) -0.0022(11) 0.0027(10) 0.0003(13) N1 0.0246(10) 0.0203(10) 0.0167(9) -0.0001(8) 0.0000(8) -0.0015(8) N2 0.0189(9) 0.0201(10) 0.0152(9) 0.0007(7) -0.0011(7) -0.0009(8) O1 0.0309(10) 0.0334(10) 0.0208(8) 0.0064(7) 0.0002(7) 0.0081(8) O2 0.0253(9) 0.0320(10) 0.0197(8) -0.0010(7) 0.0062(7) -0.0001(8) O3 0.0236(9) 0.0394(10) 0.0177(8) -0.0017(7) 0.0034(7) 0.0013(8) S1 0.0249(3) 0.0210(3) 0.0173(3) 0.0030(2) 0.0013(2) 0.0021(2) S2 0.0248(3) 0.0252(3) 0.0213(3) -0.0005(2) 0.0026(2) 0.0060(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C6 1.381(3) . ? C1 C2 1.384(3) . ? C1 N1 1.470(3) . ? C2 C3 1.391(3) . ? C3 C4 1.397(3) . ? C4 C5 1.400(3) . ? C4 C7 1.477(3) . ? C5 C6 1.387(3) . ? C7 C9 1.376(3) . ? C7 N2 1.406(3) . ? C8 N2 1.330(3) . ? C8 C11 1.466(3) . ? C8 S1 1.709(2) . ? C9 S2 1.706(2) . ? C9 S1 1.748(2) . ? C10 N2 1.480(3) . ? C11 C16 1.394(3) . ? C11 C12 1.397(3) . ? C12 C13 1.382(3) . ? C13 C14 1.394(3) . ? C14 O3 1.362(3) . ? C14 C15 1.396(3) . ? C15 C16 1.386(3) . ? C17 O3 1.434(3) . ? N1 O2 1.228(3) . ? N1 O1 1.231(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 122.8(2) . . ? C6 C1 N1 118.3(2) . . ? C2 C1 N1 118.8(2) . . ? C1 C2 C3 118.4(2) . . ? C2 C3 C4 120.3(2) . . ? C3 C4 C5 119.5(2) . . ? C3 C4 C7 121.7(2) . . ? C5 C4 C7 118.5(2) . . ? C6 C5 C4 120.6(2) . . ? C1 C6 C5 118.2(2) . . ? C9 C7 N2 113.36(19) . . ? C9 C7 C4 124.8(2) . . ? N2 C7 C4 121.80(19) . . ? N2 C8 C11 127.2(2) . . ? N2 C8 S1 110.53(16) . . ? C11 C8 S1 122.27(17) . . ? C7 C9 S2 132.43(18) . . ? C7 C9 S1 108.17(16) . . ? S2 C9 S1 119.37(13) . . ? C16 C11 C12 119.2(2) . . ? C16 C11 C8 119.3(2) . . ? C12 C11 C8 121.5(2) . . ? C13 C12 C11 120.2(2) . . ? C12 C13 C14 120.2(2) . . ? O3 C14 C13 115.1(2) . . ? O3 C14 C15 124.8(2) . . ? C13 C14 C15 120.1(2) . . ? C16 C15 C14 119.2(2) . . ? C15 C16 C11 121.0(2) . . ? O2 N1 O1 123.61(19) . . ? O2 N1 C1 117.90(19) . . ? O1 N1 C1 118.48(19) . . ? C8 N2 C7 114.75(19) . . ? C8 N2 C10 122.55(19) . . ? C7 N2 C10 121.93(18) . . ? C14 O3 C17 117.00(19) . . ? C8 S1 C9 93.13(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.421 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.086 #===END data_Compound16 _database_code_depnum_ccdc_archive 'CCDC 784451' #TrackingRef '- ESI Crystallographic Data Cantillo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 N2 O3 S2' _chemical_formula_weight 358.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1380(3) _cell_length_b 13.8360(2) _cell_length_c 11.5630(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.6420(11) _cell_angle_gamma 90.00 _cell_volume 1563.87(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10753 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Prism _exptl_crystal_colour 'Dark Red' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9316 _exptl_absorpt_correction_T_max 0.9650 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20458 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3565 _reflns_number_gt 3017 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0412P)^2^+0.9538P] 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 3565 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 S1 S 0.43386(4) 0.38961(3) 0.39606(4) 0.01752(12) Uani 1 1 d . . . S2 S 0.15456(5) 0.47339(3) 0.28722(4) 0.02004(12) Uani 1 1 d . . . O1 O 1.04249(16) 0.08832(12) 0.55676(16) 0.0438(4) Uani 1 1 d . . . O2 O 1.09598(14) 0.15771(12) 0.74304(15) 0.0375(4) Uani 1 1 d . . . O3 O -0.29176(13) 0.13169(9) 0.20072(13) 0.0247(3) Uani 1 1 d . . . N1 N 1.01416(16) 0.13624(11) 0.62888(16) 0.0235(3) Uani 1 1 d . . . N2 N 0.35881(14) 0.22566(10) 0.42857(14) 0.0155(3) Uani 1 1 d . . . C1 C 0.87292(18) 0.16991(13) 0.57862(17) 0.0198(4) Uani 1 1 d . . . C2 C 0.76598(19) 0.10848(12) 0.50220(18) 0.0208(4) Uani 1 1 d . . . H2 H 0.7830 0.0464 0.4781 0.025 Uiso 1 1 calc R . . C3 C 0.63364(18) 0.13967(12) 0.46160(17) 0.0196(4) Uani 1 1 d . . . H3 H 0.5588 0.0979 0.4112 0.023 Uiso 1 1 calc R . . C4 C 0.60950(17) 0.23281(12) 0.49458(16) 0.0165(3) Uani 1 1 d . . . C5 C 0.72109(18) 0.29392(12) 0.56788(17) 0.0185(4) Uani 1 1 d . . . H5 H 0.7053 0.3580 0.5870 0.022 Uiso 1 1 calc R . . C6 C 0.85341(18) 0.26228(13) 0.61259(17) 0.0201(4) Uani 1 1 d . . . H6 H 0.9291 0.3027 0.6653 0.024 Uiso 1 1 calc R . . C7 C 0.47153(17) 0.27219(12) 0.44489(16) 0.0165(3) Uani 1 1 d . . . C8 C 0.23836(17) 0.28042(12) 0.37050(16) 0.0157(3) Uani 1 1 d . . . C9 C 0.26157(18) 0.37596(12) 0.34937(16) 0.0168(3) Uani 1 1 d . . . C10 C 0.36484(19) 0.12991(12) 0.48823(18) 0.0206(4) Uani 1 1 d . . . H10A H 0.3464 0.0792 0.4226 0.031 Uiso 1 1 calc R . . H10B H 0.2961 0.1269 0.5180 0.031 Uiso 1 1 calc R . . H10C H 0.4560 0.1202 0.5636 0.031 Uiso 1 1 calc R . . C11 C 0.10398(17) 0.23625(12) 0.33081(16) 0.0164(3) Uani 1 1 d . . . C12 C 0.06537(18) 0.14777(12) 0.26429(17) 0.0185(4) Uani 1 1 d . . . H12 H 0.1299 0.1126 0.2494 0.022 Uiso 1 1 calc R . . C13 C -0.06550(18) 0.11003(12) 0.21933(17) 0.0184(4) Uani 1 1 d . . . H13 H -0.0896 0.0498 0.1745 0.022 Uiso 1 1 calc R . . C14 C -0.16070(17) 0.16122(13) 0.24061(17) 0.0183(4) Uani 1 1 d . . . C15 C -0.12328(18) 0.24927(13) 0.30768(18) 0.0216(4) Uani 1 1 d . . . H15 H -0.1879 0.2842 0.3227 0.026 Uiso 1 1 calc R . . C16 C 0.00645(18) 0.28599(12) 0.35221(17) 0.0193(4) Uani 1 1 d . . . H16 H 0.0303 0.3458 0.3981 0.023 Uiso 1 1 calc R . . C17 C -0.3276(2) 0.03549(14) 0.1505(2) 0.0272(4) Uani 1 1 d . . . H17A H -0.3222 0.0297 0.0686 0.041 Uiso 1 1 calc R . . H17B H -0.4211 0.0213 0.1329 0.041 Uiso 1 1 calc R . . H17C H -0.2641 -0.0104 0.2156 0.041 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 S1 0.0183(2) 0.0126(2) 0.0207(2) -0.00007(15) 0.00858(18) -0.00178(15) S2 0.0212(2) 0.0131(2) 0.0228(2) 0.00108(15) 0.00814(19) 0.00102(16) O1 0.0399(9) 0.0503(10) 0.0414(9) -0.0006(8) 0.0197(8) 0.0182(8) O2 0.0191(7) 0.0492(9) 0.0384(9) -0.0060(7) 0.0091(7) -0.0051(6) O3 0.0173(6) 0.0251(7) 0.0312(7) -0.0032(5) 0.0113(6) -0.0028(5) N1 0.0219(8) 0.0225(8) 0.0293(9) 0.0044(6) 0.0148(7) 0.0013(6) N2 0.0165(7) 0.0118(7) 0.0164(7) -0.0002(5) 0.0064(6) -0.0007(5) C1 0.0168(9) 0.0237(9) 0.0198(9) 0.0044(7) 0.0094(7) 0.0011(7) C2 0.0247(9) 0.0153(9) 0.0219(9) 0.0005(7) 0.0108(8) 0.0011(7) C3 0.0213(9) 0.0156(8) 0.0195(8) -0.0014(6) 0.0079(7) -0.0023(7) C4 0.0179(8) 0.0157(8) 0.0152(8) 0.0012(6) 0.0075(7) -0.0005(6) C5 0.0215(9) 0.0151(8) 0.0199(8) -0.0017(6) 0.0107(7) -0.0017(7) C6 0.0206(9) 0.0203(9) 0.0193(9) -0.0013(7) 0.0093(7) -0.0059(7) C7 0.0196(9) 0.0130(8) 0.0158(8) -0.0008(6) 0.0076(7) -0.0015(6) C8 0.0165(8) 0.0145(8) 0.0156(8) -0.0005(6) 0.0073(7) 0.0007(6) C9 0.0188(8) 0.0164(8) 0.0141(8) -0.0018(6) 0.0069(7) -0.0013(6) C10 0.0222(9) 0.0155(8) 0.0219(9) 0.0050(7) 0.0087(8) -0.0007(7) C11 0.0168(8) 0.0160(8) 0.0155(8) 0.0012(6) 0.0070(7) -0.0008(6) C12 0.0210(9) 0.0180(8) 0.0187(8) -0.0015(6) 0.0112(7) -0.0008(7) C13 0.0202(9) 0.0169(8) 0.0185(8) -0.0025(6) 0.0095(7) -0.0027(7) C14 0.0155(8) 0.0203(9) 0.0187(8) 0.0021(7) 0.0079(7) -0.0011(7) C15 0.0209(9) 0.0195(9) 0.0274(9) -0.0001(7) 0.0139(8) 0.0025(7) C16 0.0212(9) 0.0153(8) 0.0220(9) -0.0024(6) 0.0110(8) -0.0001(7) C17 0.0211(9) 0.0260(10) 0.0321(10) -0.0037(8) 0.0108(8) -0.0065(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S1 C7 1.7050(17) . ? S1 C9 1.7368(18) . ? S2 C9 1.7127(17) . ? O1 N1 1.219(2) . ? O2 N1 1.228(2) . ? O3 C14 1.366(2) . ? O3 C17 1.430(2) . ? N1 C1 1.467(2) . ? N2 C7 1.341(2) . ? N2 C8 1.400(2) . ? N2 C10 1.480(2) . ? C1 C2 1.383(3) . ? C1 C6 1.384(3) . ? C2 C3 1.384(3) . ? C3 C4 1.406(2) . ? C4 C5 1.403(2) . ? C4 C7 1.464(2) . ? C5 C6 1.379(3) . ? C8 C9 1.391(2) . ? C8 C11 1.472(2) . ? C11 C12 1.399(2) . ? C11 C16 1.404(2) . ? C12 C13 1.393(2) . ? C13 C14 1.392(2) . ? C14 C15 1.396(3) . ? C15 C16 1.378(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 S1 C9 93.39(8) . . ? C14 O3 C17 117.43(14) . . ? O1 N1 O2 124.38(17) . . ? O1 N1 C1 118.78(16) . . ? O2 N1 C1 116.83(15) . . ? C7 N2 C8 115.13(14) . . ? C7 N2 C10 122.25(14) . . ? C8 N2 C10 121.78(14) . . ? C2 C1 C6 122.97(17) . . ? C2 C1 N1 119.30(16) . . ? C6 C1 N1 117.71(16) . . ? C3 C2 C1 118.43(16) . . ? C2 C3 C4 120.31(16) . . ? C5 C4 C3 119.15(16) . . ? C5 C4 C7 118.18(15) . . ? C3 C4 C7 122.41(15) . . ? C6 C5 C4 120.89(16) . . ? C5 C6 C1 118.15(16) . . ? N2 C7 C4 127.76(15) . . ? N2 C7 S1 110.22(12) . . ? C4 C7 S1 122.01(12) . . ? C9 C8 N2 112.48(15) . . ? C9 C8 C11 125.93(15) . . ? N2 C8 C11 121.48(14) . . ? C8 C9 S2 132.16(14) . . ? C8 C9 S1 108.64(13) . . ? S2 C9 S1 119.20(10) . . ? C12 C11 C16 117.75(16) . . ? C12 C11 C8 122.23(15) . . ? C16 C11 C8 119.90(15) . . ? C13 C12 C11 121.59(16) . . ? C14 C13 C12 119.53(16) . . ? O3 C14 C13 124.73(16) . . ? O3 C14 C15 115.77(15) . . ? C13 C14 C15 119.49(16) . . ? C16 C15 C14 120.65(16) . . ? C15 C16 C11 120.98(16) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.428 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.071 #===END data_Compound18 _database_code_depnum_ccdc_archive 'CCDC 784452' #TrackingRef '- ESI Crystallographic Data Cantillo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 N2 O3 S2' _chemical_formula_weight 358.42 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 10.9901(7) _cell_length_b 20.0863(11) _cell_length_c 14.5576(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3213.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 66356 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour 'Dark Red' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.350 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9084 _exptl_absorpt_correction_T_max 0.9333 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21954 _diffrn_reflns_av_R_equivalents 0.0806 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2952 _reflns_number_gt 2587 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. There are chemically identical molecules in the asymmetric unit. The nitrobenzene group of the second molecule is rotationally disordered. It was refined in 2 orientations using geometrical and thermal parameter restraints. The occupancy refined to ca 65:35. ; _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^)+(0.1380P)^2^+10.4859P] 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 2952 _refine_ls_number_parameters 441 _refine_ls_number_restraints 614 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.2382 _refine_ls_wR_factor_gt 0.2279 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.67881(16) 0.14219(9) 0.19864(12) 0.0365(4) Uani 1 1 d U . . S2 S 0.57352(19) 0.27352(10) 0.25647(16) 0.0514(6) Uani 1 1 d U . . O1 O 0.9587(5) -0.1127(3) -0.0096(4) 0.0442(13) Uani 1 1 d U . . O2 O 0.9300(6) 0.4149(3) -0.0669(6) 0.077(2) Uani 1 1 d U . . O3 O 0.8099(6) 0.5024(3) -0.0803(5) 0.0561(16) Uani 1 1 d U . . N1 N 0.7256(5) 0.1827(2) 0.0390(4) 0.0327(13) Uani 1 1 d U . . N2 N 0.8278(6) 0.4422(3) -0.0605(5) 0.0483(17) Uani 1 1 d U . . C1 C 0.8911(8) -0.1740(3) 0.0018(6) 0.0441(19) Uani 1 1 d U . . H1A H 0.8881 -0.1855 0.0658 0.066 Uiso 1 1 calc R . . H1B H 0.9306 -0.2090 -0.0318 0.066 Uiso 1 1 calc R . . H1C H 0.8099 -0.1681 -0.0211 0.066 Uiso 1 1 calc R . . C2 C 0.8938(6) -0.0568(3) 0.0183(5) 0.0342(16) Uani 1 1 d U . . C3 C 0.7880(7) -0.0551(3) 0.0623(5) 0.0367(17) Uani 1 1 d U . . H3 H 0.7480 -0.0945 0.0770 0.044 Uiso 1 1 calc R . . C4 C 0.7373(7) 0.0062(3) 0.0861(5) 0.0363(16) Uani 1 1 d U . . H4 H 0.6633 0.0073 0.1172 0.044 Uiso 1 1 calc R . . C5 C 0.7943(6) 0.0647(3) 0.0647(5) 0.0285(14) Uani 1 1 d U . . C6 C 0.9047(6) 0.0626(3) 0.0175(5) 0.0314(15) Uani 1 1 d U . . H6 H 0.9428 0.1021 0.0008 0.038 Uiso 1 1 calc R . . C7 C 0.9566(7) 0.0045(4) -0.0042(5) 0.0363(16) Uani 1 1 d U . . H7 H 1.0319 0.0034 -0.0333 0.044 Uiso 1 1 calc R . . C8 C 0.7403(7) 0.1291(3) 0.0920(5) 0.0365(16) Uani 1 1 d U . . C9 C 0.6369(6) 0.2238(3) 0.1734(5) 0.0348(16) Uani 1 1 d U . . C10 C 0.6718(6) 0.2377(3) 0.0840(5) 0.0314(14) Uani 1 1 d U . . C11 C 0.7529(8) 0.1847(3) -0.0575(5) 0.0357(16) Uani 1 1 d U . . H11A H 0.8294 0.2068 -0.0667 0.054 Uiso 1 1 calc R . . H11B H 0.6899 0.2086 -0.0891 0.054 Uiso 1 1 calc R . . H11C H 0.7575 0.1402 -0.0810 0.054 Uiso 1 1 calc R . . C12 C 0.6552(7) 0.3042(3) 0.0431(5) 0.0362(16) Uani 1 1 d U . . C13 C 0.7473(9) 0.3379(3) 0.0032(5) 0.0443(17) Uani 1 1 d U . . H13 H 0.8239 0.3189 -0.0035 0.053 Uiso 1 1 calc R . . C14 C 0.7225(7) 0.4039(3) -0.0282(5) 0.0411(16) Uani 1 1 d U . . C15 C 0.6121(7) 0.4330(4) -0.0226(5) 0.0430(17) Uani 1 1 d U . . H15 H 0.6018 0.4766 -0.0424 0.052 Uiso 1 1 calc R . . C16 C 0.5134(8) 0.3977(4) 0.0128(6) 0.0478(19) Uani 1 1 d U . . H16 H 0.4350 0.4151 0.0136 0.057 Uiso 1 1 calc R . . C17 C 0.5407(8) 0.3343(3) 0.0470(5) 0.0419(17) Uani 1 1 d U . . H17 H 0.4779 0.3105 0.0744 0.050 Uiso 1 1 calc R . . S3 S 0.17093(16) 0.36439(8) 0.07082(12) 0.0329(4) Uani 1 1 d U . . S4 S 0.06122(19) 0.23382(10) 0.01769(17) 0.0514(6) Uani 1 1 d U . . O4 O 0.4584(5) 0.6200(2) 0.2703(4) 0.0387(12) Uani 1 1 d U . . N4 N 0.2361(5) 0.3227(2) 0.2269(4) 0.0312(13) Uani 1 1 d U A . C18 C 0.3992(8) 0.6824(3) 0.2569(7) 0.047(2) Uani 1 1 d U . . H18A H 0.4022 0.6942 0.1931 0.071 Uiso 1 1 calc R . . H18B H 0.4396 0.7160 0.2925 0.071 Uiso 1 1 calc R . . H18C H 0.3159 0.6790 0.2762 0.071 Uiso 1 1 calc R . . C19 C 0.4044(7) 0.5651(3) 0.2458(5) 0.0357(16) Uani 1 1 d U . . C20 C 0.2894(7) 0.5623(3) 0.1988(6) 0.0347(16) Uani 1 1 d U . . H20 H 0.2500 0.6018 0.1835 0.042 Uiso 1 1 calc R . . C21 C 0.2366(7) 0.5026(3) 0.1759(5) 0.0332(16) Uani 1 1 d U . . H21 H 0.1631 0.5020 0.1443 0.040 Uiso 1 1 calc R . . C22 C 0.2948(6) 0.4409(3) 0.2009(5) 0.0327(15) Uani 1 1 d U . . C23 C 0.4106(6) 0.4432(3) 0.2425(6) 0.0385(18) Uani 1 1 d U . . H23 H 0.4537 0.4042 0.2535 0.046 Uiso 1 1 calc R . . C24 C 0.4602(6) 0.5053(4) 0.2673(6) 0.0391(17) Uani 1 1 d U . . H24 H 0.5334 0.5061 0.2994 0.047 Uiso 1 1 calc R . . C25 C 0.2392(7) 0.3784(3) 0.1738(5) 0.0300(14) Uani 1 1 d U . . C26 C 0.1347(6) 0.2817(3) 0.0981(6) 0.0359(16) Uani 1 1 d U A . C27 C 0.1799(7) 0.2690(3) 0.1851(5) 0.0364(15) Uani 1 1 d U . . C28 C 0.2617(10) 0.3263(4) 0.3280(6) 0.053(2) Uani 1 1 d U . . H28A H 0.3451 0.3146 0.3391 0.080 Uiso 1 1 calc R A . H28B H 0.2095 0.2958 0.3600 0.080 Uiso 1 1 calc R . . H28C H 0.2469 0.3707 0.3495 0.080 Uiso 1 1 calc R . . C29A C 0.1981(5) 0.2042(2) 0.2367(4) 0.0294(18) Uani 0.640(4) 1 d PGU A 1 C30A C 0.3095(4) 0.1825(2) 0.2706(5) 0.0294(18) Uani 0.640(4) 1 d PGU A 1 H30A H 0.3764 0.2108 0.2698 0.035 Uiso 0.640(4) 1 calc PR A 1 C31A C 0.3209(5) 0.1184(3) 0.3057(5) 0.0322(19) Uani 0.640(4) 1 d PGU A 1 H31A H 0.3954 0.1039 0.3284 0.039 Uiso 0.640(4) 1 calc PR A 1 C32A C 0.2209(6) 0.0760(2) 0.3068(5) 0.0281(18) Uani 0.640(4) 1 d PGU A 1 H32A H 0.2286 0.0332 0.3302 0.034 Uiso 0.640(4) 1 calc PR A 1 C33A C 0.1096(5) 0.0977(2) 0.2728(5) 0.0287(17) Uani 0.640(4) 1 d PGU A 1 C34A C 0.0982(4) 0.1618(3) 0.2378(5) 0.0309(19) Uani 0.640(4) 1 d PGU A 1 H34A H 0.0236 0.1763 0.2151 0.037 Uiso 0.640(4) 1 calc PR A 1 N5A N 0.0085(8) 0.0542(4) 0.2746(6) 0.0306(16) Uani 0.640(4) 1 d PU A 1 O5A O 0.0284(8) -0.0070(4) 0.2733(6) 0.0420(17) Uani 0.640(4) 1 d PU A 1 O6A O -0.0931(7) 0.0786(4) 0.2825(7) 0.0437(18) Uani 0.640(4) 1 d PU A 1 C29B C 0.1499(9) 0.1993(4) 0.2242(8) 0.0294(18) Uani 0.360(4) 1 d PGU A 2 C30B C 0.2497(8) 0.1648(4) 0.2585(9) 0.0294(18) Uani 0.360(4) 1 d PGU A 2 H30B H 0.3248 0.1859 0.2634 0.035 Uiso 0.360(4) 1 calc PR A 2 C31B C 0.2374(9) 0.0988(4) 0.2856(10) 0.0322(19) Uani 0.360(4) 1 d PGU A 2 C32B C 0.1253(11) 0.0672(4) 0.2783(9) 0.0281(18) Uani 0.360(4) 1 d PGU A 2 H32B H 0.1170 0.0231 0.2964 0.034 Uiso 0.360(4) 1 calc PR A 2 C33B C 0.0255(9) 0.1017(5) 0.2440(10) 0.0287(17) Uani 0.360(4) 1 d PGU A 2 H33B H -0.0496 0.0806 0.2391 0.034 Uiso 0.360(4) 1 calc PR A 2 C34B C 0.0378(8) 0.1677(4) 0.2170(9) 0.0309(19) Uani 0.360(4) 1 d PGU A 2 H34B H -0.0290 0.1908 0.1940 0.037 Uiso 0.360(4) 1 calc PR A 2 N5B N 0.3317(15) 0.0585(7) 0.3213(13) 0.0306(16) Uani 0.360(4) 1 d PU A 2 O5B O 0.3151(14) 0.0007(6) 0.3375(11) 0.0420(17) Uani 0.360(4) 1 d PU A 2 O6B O 0.4365(13) 0.0870(7) 0.3237(12) 0.0437(18) Uani 0.360(4) 1 d PU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0373(9) 0.0370(9) 0.0353(9) 0.0086(7) 0.0079(8) 0.0111(7) S2 0.0499(11) 0.0536(11) 0.0506(12) -0.0001(10) 0.0024(10) 0.0275(9) O1 0.042(3) 0.039(2) 0.052(3) -0.007(2) 0.006(3) 0.011(2) O2 0.064(3) 0.067(4) 0.100(5) 0.043(4) 0.022(4) 0.012(3) O3 0.074(4) 0.033(2) 0.062(4) 0.004(3) 0.006(3) -0.014(2) N1 0.040(3) 0.022(2) 0.036(3) -0.004(2) -0.009(3) -0.013(2) N2 0.050(3) 0.041(3) 0.054(4) 0.001(3) 0.001(3) 0.000(3) C1 0.057(4) 0.035(3) 0.041(4) 0.000(3) -0.003(4) 0.018(3) C2 0.034(3) 0.026(2) 0.042(4) -0.001(3) -0.001(3) 0.009(2) C3 0.043(4) 0.031(3) 0.036(4) 0.010(3) 0.007(3) 0.006(3) C4 0.034(3) 0.032(3) 0.043(4) 0.011(3) -0.001(3) 0.007(3) C5 0.032(3) 0.028(2) 0.026(3) 0.002(3) -0.012(3) 0.003(2) C6 0.030(3) 0.035(3) 0.029(3) 0.006(3) -0.003(3) 0.004(2) C7 0.032(3) 0.042(3) 0.034(4) -0.011(3) -0.001(3) -0.011(3) C8 0.036(3) 0.034(3) 0.040(4) 0.005(3) 0.004(3) 0.007(3) C9 0.034(3) 0.032(3) 0.038(3) 0.002(3) -0.010(3) 0.014(3) C10 0.028(3) 0.024(3) 0.042(3) 0.000(2) -0.009(3) -0.001(2) C11 0.042(4) 0.033(3) 0.032(3) 0.004(3) -0.002(3) -0.014(3) C12 0.052(4) 0.026(3) 0.030(3) 0.002(2) -0.010(3) -0.002(3) C13 0.060(4) 0.037(3) 0.036(4) -0.006(3) -0.004(3) -0.012(3) C14 0.052(3) 0.036(3) 0.035(4) -0.005(3) -0.008(3) -0.009(3) C15 0.051(4) 0.049(4) 0.029(4) -0.011(3) -0.006(3) -0.013(3) C16 0.049(4) 0.037(3) 0.058(5) 0.008(4) -0.009(4) -0.005(3) C17 0.063(4) 0.024(3) 0.039(4) -0.005(3) -0.014(3) 0.007(3) S3 0.0357(9) 0.0268(7) 0.0362(9) 0.0052(7) -0.0017(8) -0.0081(7) S4 0.0523(12) 0.0393(9) 0.0626(14) -0.0071(10) 0.0027(11) -0.0201(9) O4 0.040(3) 0.033(2) 0.044(3) 0.001(2) -0.001(2) -0.008(2) N4 0.035(3) 0.027(2) 0.033(3) 0.013(2) 0.007(2) 0.003(2) C18 0.054(5) 0.027(3) 0.060(5) 0.010(4) 0.003(5) 0.003(3) C19 0.039(3) 0.034(3) 0.034(4) 0.006(3) 0.002(3) -0.010(3) C20 0.044(4) 0.025(3) 0.036(4) 0.010(3) 0.002(3) -0.003(3) C21 0.033(3) 0.027(3) 0.040(4) 0.006(3) -0.009(3) 0.004(3) C22 0.037(3) 0.026(3) 0.034(4) 0.001(3) -0.015(3) 0.005(2) C23 0.029(3) 0.033(3) 0.054(5) -0.005(3) -0.009(3) 0.007(3) C24 0.026(3) 0.040(3) 0.051(4) 0.010(3) -0.006(3) -0.013(3) C25 0.031(3) 0.028(2) 0.031(3) 0.000(2) 0.002(3) 0.006(3) C26 0.033(3) 0.021(3) 0.054(4) -0.003(3) 0.003(3) 0.007(3) C27 0.048(4) 0.025(3) 0.036(3) 0.007(2) 0.020(3) 0.007(2) C28 0.082(6) 0.040(4) 0.038(4) 0.007(3) 0.005(4) 0.024(5) C29A 0.025(4) 0.017(2) 0.046(4) -0.004(3) 0.003(4) -0.001(3) C30A 0.018(4) 0.024(3) 0.047(5) -0.005(3) 0.008(4) 0.001(3) C31A 0.023(3) 0.027(3) 0.047(5) 0.001(3) 0.007(4) 0.001(3) C32A 0.025(3) 0.020(3) 0.039(5) -0.003(3) 0.008(3) 0.002(3) C33A 0.028(3) 0.018(3) 0.041(4) -0.005(3) 0.003(4) 0.002(3) C34A 0.013(4) 0.031(3) 0.049(5) 0.011(3) 0.011(4) 0.005(3) N5A 0.030(3) 0.026(3) 0.036(4) 0.000(3) -0.003(3) -0.003(2) O5A 0.051(4) 0.027(2) 0.048(4) 0.000(3) 0.004(4) 0.005(3) O6A 0.031(3) 0.039(3) 0.062(5) 0.005(3) -0.005(3) 0.004(3) C29B 0.025(4) 0.017(2) 0.046(4) -0.004(3) 0.003(4) -0.001(3) C30B 0.018(4) 0.024(3) 0.047(5) -0.005(3) 0.008(4) 0.001(3) C31B 0.023(3) 0.027(3) 0.047(5) 0.001(3) 0.007(4) 0.001(3) C32B 0.025(3) 0.020(3) 0.039(5) -0.003(3) 0.008(3) 0.002(3) C33B 0.028(3) 0.018(3) 0.041(4) -0.005(3) 0.003(4) 0.002(3) C34B 0.013(4) 0.031(3) 0.049(5) 0.011(3) 0.011(4) 0.005(3) N5B 0.030(3) 0.026(3) 0.036(4) 0.000(3) -0.003(3) -0.003(2) O5B 0.051(4) 0.027(2) 0.048(4) 0.000(3) 0.004(4) 0.005(3) O6B 0.031(3) 0.039(3) 0.062(5) 0.005(3) -0.005(3) 0.004(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S1 C8 1.714(8) . ? S1 C9 1.742(7) . ? S2 C9 1.715(8) . ? O1 C2 1.391(8) . ? O1 C1 1.447(9) . ? O2 N2 1.253(9) . ? O3 N2 1.258(8) . ? N1 C8 1.335(9) . ? N1 C10 1.413(9) . ? N1 C11 1.436(9) . ? N2 C14 1.466(10) . ? C2 C3 1.328(10) . ? C2 C7 1.448(10) . ? C3 C4 1.396(9) . ? C4 C5 1.368(9) . ? C5 C6 1.396(10) . ? C5 C8 1.476(9) . ? C6 C7 1.337(10) . ? C9 C10 1.386(11) . ? C10 C12 1.475(9) . ? C12 C13 1.348(11) . ? C12 C17 1.398(11) . ? C13 C14 1.429(10) . ? C14 C15 1.348(11) . ? C15 C16 1.393(11) . ? C16 C17 1.400(10) . ? S3 C25 1.700(8) . ? S3 C26 1.754(7) . ? S4 C26 1.716(8) . ? O4 C19 1.302(8) . ? O4 C18 1.425(8) . ? N4 C25 1.361(8) . ? N4 C27 1.384(9) . ? N4 C28 1.499(11) . ? C19 C24 1.385(10) . ? C19 C20 1.439(11) . ? C20 C21 1.373(9) . ? C21 C22 1.442(9) . ? C22 C23 1.411(10) . ? C22 C25 1.450(9) . ? C23 C24 1.408(10) . ? C26 C27 1.384(12) . ? C27 C29A 1.517(8) . ? C27 C29B 1.548(10) . ? C29A C30A 1.3900 . ? C29A C34A 1.3900 . ? C30A C31A 1.3900 . ? C31A C32A 1.3900 . ? C32A C33A 1.3900 . ? C33A C34A 1.3900 . ? C33A N5A 1.414(9) . ? N5A O6A 1.225(11) . ? N5A O5A 1.249(11) . ? C29B C30B 1.3900 . ? C29B C34B 1.3900 . ? C30B C31B 1.3900 . ? C31B C32B 1.3900 . ? C31B N5B 1.414(18) . ? C32B C33B 1.3900 . ? C33B C34B 1.3900 . ? N5B O5B 1.20(2) . ? N5B O6B 1.29(2) . ? 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 C8 S1 C9 93.3(3) . . ? C2 O1 C1 113.0(6) . . ? C8 N1 C10 114.4(6) . . ? C8 N1 C11 124.2(6) . . ? C10 N1 C11 121.2(6) . . ? O2 N2 O3 122.9(7) . . ? O2 N2 C14 120.1(6) . . ? O3 N2 C14 117.0(7) . . ? C3 C2 O1 127.6(6) . . ? C3 C2 C7 120.4(6) . . ? O1 C2 C7 112.0(6) . . ? C2 C3 C4 119.4(6) . . ? C5 C4 C3 121.2(7) . . ? C6 C5 C4 118.9(6) . . ? C6 C5 C8 120.6(6) . . ? C4 C5 C8 120.5(6) . . ? C7 C6 C5 121.0(6) . . ? C6 C7 C2 119.0(7) . . ? N1 C8 C5 126.9(7) . . ? N1 C8 S1 110.6(5) . . ? C5 C8 S1 122.4(5) . . ? C10 C9 S2 131.1(5) . . ? C10 C9 S1 108.3(5) . . ? S2 C9 S1 120.4(4) . . ? C9 C10 N1 113.2(6) . . ? C9 C10 C12 121.8(6) . . ? N1 C10 C12 124.9(7) . . ? C13 C12 C17 118.5(7) . . ? C13 C12 C10 122.4(7) . . ? C17 C12 C10 119.1(7) . . ? C12 C13 C14 117.4(8) . . ? C15 C14 C13 123.6(7) . . ? C15 C14 N2 120.2(7) . . ? C13 C14 N2 116.0(7) . . ? C14 C15 C16 120.2(7) . . ? C17 C16 C15 115.3(8) . . ? C12 C17 C16 124.8(7) . . ? C25 S3 C26 93.3(4) . . ? C19 O4 C18 119.9(6) . . ? C25 N4 C27 113.7(6) . . ? C25 N4 C28 120.9(6) . . ? C27 N4 C28 123.6(6) . . ? O4 C19 C24 118.1(7) . . ? O4 C19 C20 124.3(6) . . ? C24 C19 C20 117.6(6) . . ? C21 C20 C19 121.4(6) . . ? C20 C21 C22 120.2(7) . . ? C23 C22 C21 118.7(6) . . ? C23 C22 C25 121.7(6) . . ? C21 C22 C25 119.3(6) . . ? C24 C23 C22 119.3(6) . . ? C19 C24 C23 122.6(7) . . ? N4 C25 C22 124.6(7) . . ? N4 C25 S3 110.7(5) . . ? C22 C25 S3 124.7(5) . . ? C27 C26 S4 133.6(5) . . ? C27 C26 S3 107.4(5) . . ? S4 C26 S3 118.9(5) . . ? C26 C27 N4 114.8(6) . . ? C26 C27 C29A 131.2(6) . . ? N4 C27 C29A 113.1(6) . . ? C26 C27 C29B 115.3(7) . . ? N4 C27 C29B 129.6(7) . . ? C29A C27 C29B 21.4(4) . . ? C30A C29A C34A 120.0 . . ? C30A C29A C27 124.2(4) . . ? C34A C29A C27 115.3(4) . . ? C31A C30A C29A 120.0 . . ? C32A C31A C30A 120.0 . . ? C33A C32A C31A 120.0 . . ? C32A C33A C34A 120.0 . . ? C32A C33A N5A 119.5(5) . . ? C34A C33A N5A 120.5(5) . . ? C33A C34A C29A 120.0 . . ? O6A N5A O5A 123.7(9) . . ? O6A N5A C33A 118.0(7) . . ? O5A N5A C33A 118.1(8) . . ? C30B C29B C34B 120.0 . . ? C30B C29B C27 114.5(6) . . ? C34B C29B C27 125.0(6) . . ? C29B C30B C31B 120.0 . . ? C30B C31B C32B 120.0 . . ? C30B C31B N5B 125.4(9) . . ? C32B C31B N5B 114.6(9) . . ? C33B C32B C31B 120.0 . . ? C34B C33B C32B 120.0 . . ? C33B C34B C29B 120.0 . . ? O5B N5B O6B 124.2(16) . . ? O5B N5B C31B 121.0(15) . . ? O6B N5B C31B 114.3(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.621 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.093