# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_dp_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N2 O2 S2' _chemical_formula_weight 419.52 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 7.5669(4) _cell_length_b 10.6356(5) _cell_length_c 24.4275(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.345(2) _cell_angle_gamma 90.00 _cell_volume 1949.76(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20029 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3878 _reflns_number_gt 3012 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3878 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1476 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 S1 S 0.73637(8) 0.21013(5) 0.06383(3) 0.0703(2) Uani 1 1 d . . . S2 S 0.39422(7) 0.00199(4) 0.069275(19) 0.0554(2) Uani 1 1 d . . . O2 O 0.98152(19) 0.73658(14) 0.05839(7) 0.0761(5) Uani 1 1 d . . . O1 O 0.71061(16) -0.44153(11) 0.19141(5) 0.0575(4) Uani 1 1 d . . . C1 C 0.8897(3) 0.8276(2) 0.02244(11) 0.0806(7) Uani 1 1 d . . . H3 H 0.8939 0.8032 -0.0152 0.121 Uiso 1 1 calc R . . H1 H 0.9456 0.9082 0.0290 0.121 Uiso 1 1 calc R . . H19 H 0.7678 0.8327 0.0293 0.121 Uiso 1 1 calc R . . C2 C 0.9175(2) 0.61650(18) 0.05685(8) 0.0538(5) Uani 1 1 d . . . C3 C 0.7777(2) 0.57398(19) 0.02050(8) 0.0571(5) Uani 1 1 d . . . H4 H 0.7196 0.6279 -0.0059 0.069 Uiso 1 1 calc R . . C4 C 0.7236(3) 0.45045(19) 0.02320(8) 0.0587(5) Uani 1 1 d . . . H5 H 0.6289 0.4216 -0.0017 0.070 Uiso 1 1 calc R . . C5 C 0.8072(3) 0.36895(17) 0.06215(8) 0.0539(5) Uani 1 1 d . . . C6 C 0.5713(2) 0.22003(15) 0.10748(7) 0.0450(4) Uani 1 1 d . . . C7 C 0.4401(2) 0.13278(15) 0.11185(7) 0.0434(4) Uani 1 1 d . . . C8 C 0.4964(2) -0.12435(15) 0.10909(7) 0.0424(4) Uani 1 1 d . . . C9 C 0.4144(2) -0.24043(17) 0.10308(8) 0.0506(5) Uani 1 1 d . . . H8 H 0.3064 -0.2488 0.0805 0.061 Uiso 1 1 calc R . . C10 C 0.4917(2) -0.34369(16) 0.13037(9) 0.0525(5) Uani 1 1 d . . . H9 H 0.4371 -0.4219 0.1251 0.063 Uiso 1 1 calc R . . C11 C 0.6474(2) -0.33308(15) 0.16508(7) 0.0440(4) Uani 1 1 d . . . C12 C 0.8637(3) -0.4330(2) 0.23129(10) 0.0749(6) Uani 1 1 d . . . H6 H 0.9606 -0.3979 0.2145 0.112 Uiso 1 1 calc R . . H7 H 0.8959 -0.5154 0.2452 0.112 Uiso 1 1 calc R . . H2 H 0.8383 -0.3800 0.2611 0.112 Uiso 1 1 calc R . . N1 N 0.55972(19) 0.31428(13) 0.14544(6) 0.0494(4) Uani 1 1 d . . . H16 H 0.6286 0.3787 0.1501 0.059 Uiso 1 1 calc R . . C14 C 0.4204(2) 0.28885(15) 0.17468(7) 0.0449(4) Uani 1 1 d . . . C15 C 0.3419(2) 0.17603(15) 0.15473(7) 0.0431(4) Uani 1 1 d . . . C16 C 0.6546(3) -0.11490(16) 0.14317(8) 0.0558(5) Uani 1 1 d . . . H11 H 0.7116 -0.0374 0.1473 0.067 Uiso 1 1 calc R . . C17 C 0.7311(3) -0.21727(16) 0.17149(8) 0.0550(5) Uani 1 1 d . . . H10 H 0.8379 -0.2087 0.1947 0.066 Uiso 1 1 calc R . . C18 C 0.1971(3) 0.12831(18) 0.17822(9) 0.0572(5) Uani 1 1 d . . . H15 H 0.1420 0.0540 0.1653 0.069 Uiso 1 1 calc R . . C19 C 0.1378(3) 0.1937(2) 0.22085(10) 0.0681(6) Uani 1 1 d . . . H14 H 0.0420 0.1625 0.2370 0.082 Uiso 1 1 calc R . . C20 C 0.2178(3) 0.3057(2) 0.24040(9) 0.0698(6) Uani 1 1 d . . . H12 H 0.1746 0.3474 0.2694 0.084 Uiso 1 1 calc R . . C21 C 0.3594(3) 0.35590(18) 0.21764(8) 0.0563(5) Uani 1 1 d . . . H13 H 0.4121 0.4312 0.2303 0.068 Uiso 1 1 calc R . . C22 C 0.9514(3) 0.4127(2) 0.09840(9) 0.0617(5) Uani 1 1 d . . . H18 H 1.0114 0.3588 0.1244 0.074 Uiso 1 1 calc R . . C23 C 1.0044(3) 0.5358(2) 0.09552(9) 0.0648(6) Uani 1 1 d . . . H17 H 1.1000 0.5650 0.1199 0.078 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 0.0821(4) 0.0463(3) 0.0912(5) -0.0050(3) 0.0439(3) -0.0037(2) S2 0.0785(4) 0.0368(3) 0.0470(3) -0.00003(18) -0.0073(3) -0.0030(2) O2 0.0605(9) 0.0582(9) 0.1072(12) 0.0230(8) 0.0021(9) -0.0142(7) O1 0.0602(8) 0.0366(7) 0.0712(9) 0.0014(6) -0.0085(7) 0.0013(6) C1 0.0778(15) 0.0581(13) 0.1083(19) 0.0300(13) 0.0215(14) 0.0052(11) C2 0.0422(10) 0.0556(11) 0.0654(12) 0.0157(9) 0.0143(9) -0.0035(8) C3 0.0507(11) 0.0604(12) 0.0600(12) 0.0143(10) 0.0062(9) 0.0031(9) C4 0.0502(11) 0.0638(13) 0.0613(12) 0.0014(10) 0.0045(9) -0.0036(9) C5 0.0520(11) 0.0520(11) 0.0615(12) 0.0056(9) 0.0222(10) -0.0019(9) C6 0.0554(11) 0.0318(9) 0.0486(10) 0.0024(7) 0.0092(8) 0.0007(7) C7 0.0525(10) 0.0322(8) 0.0447(10) 0.0035(7) 0.0033(8) -0.0008(7) C8 0.0516(10) 0.0337(8) 0.0417(9) -0.0035(7) 0.0053(8) -0.0024(7) C9 0.0459(10) 0.0420(10) 0.0602(11) -0.0033(8) -0.0072(8) -0.0057(8) C10 0.0516(10) 0.0332(9) 0.0704(12) -0.0035(8) -0.0017(9) -0.0079(7) C11 0.0487(10) 0.0333(8) 0.0502(10) -0.0022(7) 0.0070(8) -0.0002(7) C12 0.0784(14) 0.0573(13) 0.0805(15) 0.0087(11) -0.0219(12) 0.0054(11) N1 0.0561(9) 0.0308(7) 0.0629(10) -0.0030(6) 0.0137(8) -0.0059(6) C14 0.0524(10) 0.0344(9) 0.0478(10) 0.0056(7) 0.0058(8) 0.0057(7) C15 0.0501(10) 0.0332(8) 0.0454(9) 0.0080(7) 0.0035(8) 0.0034(7) C16 0.0645(12) 0.0359(10) 0.0635(12) -0.0007(8) -0.0055(10) -0.0151(8) C17 0.0532(11) 0.0436(10) 0.0630(12) -0.0038(9) -0.0123(9) -0.0071(8) C18 0.0583(12) 0.0453(10) 0.0693(13) 0.0138(9) 0.0129(10) -0.0025(8) C19 0.0705(14) 0.0627(14) 0.0769(15) 0.0202(12) 0.0322(12) 0.0065(11) C20 0.0864(16) 0.0660(14) 0.0620(13) 0.0097(11) 0.0285(13) 0.0261(12) C21 0.0704(13) 0.0423(10) 0.0562(12) -0.0025(8) 0.0082(10) 0.0121(9) C22 0.0555(11) 0.0630(13) 0.0671(13) 0.0236(10) 0.0101(10) 0.0008(10) C23 0.0476(11) 0.0726(14) 0.0717(13) 0.0212(12) -0.0018(10) -0.0089(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.7457(18) . ? S1 C5 1.7742(19) . ? S2 C7 1.7449(17) . ? S2 C8 1.7767(17) . ? O2 C2 1.365(2) . ? O2 C1 1.427(3) . ? O1 C11 1.376(2) . ? O1 C12 1.418(2) . ? C1 H3 0.9600 . ? C1 H1 0.9600 . ? C1 H19 0.9600 . ? C2 C3 1.368(3) . ? C2 C23 1.379(3) . ? C3 C4 1.380(3) . ? C3 H4 0.9300 . ? C4 C5 1.379(3) . ? C4 H5 0.9300 . ? C5 C22 1.394(3) . ? C6 C7 1.373(2) . ? C6 N1 1.376(2) . ? C7 C15 1.435(2) . ? C8 C16 1.372(2) . ? C8 C9 1.381(2) . ? C9 C10 1.376(3) . ? C9 H8 0.9300 . ? C10 C11 1.366(3) . ? C10 H9 0.9300 . ? C11 C17 1.385(2) . ? C12 H6 0.9600 . ? C12 H7 0.9600 . ? C12 H2 0.9600 . ? N1 C14 1.374(2) . ? N1 H16 0.8600 . ? C14 C21 1.395(2) . ? C14 C15 1.398(2) . ? C15 C18 1.396(2) . ? C16 C17 1.377(2) . ? C16 H11 0.9300 . ? C17 H10 0.9300 . ? C18 C19 1.375(3) . ? C18 H15 0.9300 . ? C19 C20 1.392(3) . ? C19 H14 0.9300 . ? C20 C21 1.377(3) . ? C20 H12 0.9300 . ? C21 H13 0.9300 . ? C22 C23 1.374(3) . ? C22 H18 0.9300 . ? C23 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 S1 C5 101.45(8) . . ? C7 S2 C8 103.72(8) . . ? C2 O2 C1 118.35(17) . . ? C11 O1 C12 118.18(14) . . ? O2 C1 H3 109.5 . . ? O2 C1 H1 109.5 . . ? H3 C1 H1 109.5 . . ? O2 C1 H19 109.5 . . ? H3 C1 H19 109.5 . . ? H1 C1 H19 109.5 . . ? O2 C2 C3 124.72(17) . . ? O2 C2 C23 115.28(18) . . ? C3 C2 C23 120.00(18) . . ? C2 C3 C4 119.56(18) . . ? C2 C3 H4 120.2 . . ? C4 C3 H4 120.2 . . ? C5 C4 C3 121.22(19) . . ? C5 C4 H5 119.4 . . ? C3 C4 H5 119.4 . . ? C4 C5 C22 118.76(18) . . ? C4 C5 S1 120.07(16) . . ? C22 C5 S1 121.13(15) . . ? C7 C6 N1 109.32(15) . . ? C7 C6 S1 125.98(13) . . ? N1 C6 S1 124.60(13) . . ? C6 C7 C15 106.68(15) . . ? C6 C7 S2 125.68(13) . . ? C15 C7 S2 127.47(13) . . ? C16 C8 C9 118.38(15) . . ? C16 C8 S2 124.17(13) . . ? C9 C8 S2 117.38(13) . . ? C10 C9 C8 120.31(16) . . ? C10 C9 H8 119.8 . . ? C8 C9 H8 119.8 . . ? C11 C10 C9 120.97(16) . . ? C11 C10 H9 119.5 . . ? C9 C10 H9 119.5 . . ? C10 C11 O1 116.20(15) . . ? C10 C11 C17 119.32(16) . . ? O1 C11 C17 124.48(16) . . ? O1 C12 H6 109.5 . . ? O1 C12 H7 109.5 . . ? H6 C12 H7 109.5 . . ? O1 C12 H2 109.5 . . ? H6 C12 H2 109.5 . . ? H7 C12 H2 109.5 . . ? C14 N1 C6 109.05(14) . . ? C14 N1 H16 125.5 . . ? C6 N1 H16 125.5 . . ? N1 C14 C21 129.79(17) . . ? N1 C14 C15 107.91(14) . . ? C21 C14 C15 122.29(17) . . ? C18 C15 C14 119.30(17) . . ? C18 C15 C7 133.65(17) . . ? C14 C15 C7 107.04(15) . . ? C8 C16 C17 121.70(16) . . ? C8 C16 H11 119.2 . . ? C17 C16 H11 119.2 . . ? C16 C17 C11 119.29(17) . . ? C16 C17 H10 120.4 . . ? C11 C17 H10 120.4 . . ? C19 C18 C15 118.48(19) . . ? C19 C18 H15 120.8 . . ? C15 C18 H15 120.8 . . ? C18 C19 C20 121.54(19) . . ? C18 C19 H14 119.2 . . ? C20 C19 H14 119.2 . . ? C21 C20 C19 121.34(19) . . ? C21 C20 H12 119.3 . . ? C19 C20 H12 119.3 . . ? C20 C21 C14 117.05(19) . . ? C20 C21 H13 121.5 . . ? C14 C21 H13 121.5 . . ? C23 C22 C5 119.69(18) . . ? C23 C22 H18 120.2 . . ? C5 C22 H18 120.2 . . ? C22 C23 C2 120.76(19) . . ? C22 C23 H17 119.6 . . ? C2 C23 H17 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O2 C2 C3 4.7(3) . . . . ? C1 O2 C2 C23 -175.30(19) . . . . ? O2 C2 C3 C4 -179.39(18) . . . . ? C23 C2 C3 C4 0.6(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C22 -1.4(3) . . . . ? C3 C4 C5 S1 -179.06(15) . . . . ? C6 S1 C5 C4 -88.85(17) . . . . ? C6 S1 C5 C22 93.57(17) . . . . ? C5 S1 C6 C7 161.50(17) . . . . ? C5 S1 C6 N1 -22.54(17) . . . . ? N1 C6 C7 C15 0.22(19) . . . . ? S1 C6 C7 C15 176.71(13) . . . . ? N1 C6 C7 S2 175.76(12) . . . . ? S1 C6 C7 S2 -7.8(2) . . . . ? C8 S2 C7 C6 100.73(16) . . . . ? C8 S2 C7 C15 -84.65(16) . . . . ? C7 S2 C8 C16 -36.61(18) . . . . ? C7 S2 C8 C9 146.49(14) . . . . ? C16 C8 C9 C10 -0.7(3) . . . . ? S2 C8 C9 C10 176.39(14) . . . . ? C8 C9 C10 C11 2.0(3) . . . . ? C9 C10 C11 O1 178.28(17) . . . . ? C9 C10 C11 C17 -2.0(3) . . . . ? C12 O1 C11 C10 -174.83(19) . . . . ? C12 O1 C11 C17 5.5(3) . . . . ? C7 C6 N1 C14 -0.1(2) . . . . ? S1 C6 N1 C14 -176.65(13) . . . . ? C6 N1 C14 C21 178.94(18) . . . . ? C6 N1 C14 C15 -0.06(19) . . . . ? N1 C14 C15 C18 179.35(16) . . . . ? C21 C14 C15 C18 0.2(3) . . . . ? N1 C14 C15 C7 0.20(18) . . . . ? C21 C14 C15 C7 -178.90(16) . . . . ? C6 C7 C15 C18 -179.23(19) . . . . ? S2 C7 C15 C18 5.3(3) . . . . ? C6 C7 C15 C14 -0.26(19) . . . . ? S2 C7 C15 C14 -175.69(13) . . . . ? C9 C8 C16 C17 -0.6(3) . . . . ? S2 C8 C16 C17 -177.48(15) . . . . ? C8 C16 C17 C11 0.6(3) . . . . ? C10 C11 C17 C16 0.7(3) . . . . ? O1 C11 C17 C16 -179.61(17) . . . . ? C14 C15 C18 C19 -0.8(3) . . . . ? C7 C15 C18 C19 178.11(19) . . . . ? C15 C18 C19 C20 0.5(3) . . . . ? C18 C19 C20 C21 0.3(3) . . . . ? C19 C20 C21 C14 -0.8(3) . . . . ? N1 C14 C21 C20 -178.35(18) . . . . ? C15 C14 C21 C20 0.5(3) . . . . ? C4 C5 C22 C23 1.5(3) . . . . ? S1 C5 C22 C23 179.11(16) . . . . ? C5 C22 C23 C2 -0.5(3) . . . . ? O2 C2 C23 C22 179.5(2) . . . . ? C3 C2 C23 C22 -0.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.278 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 952234' ####################################################################### # # 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_NO2_mono _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H9 N2 O2 S, C H3' _chemical_formula_sum 'C14 H12 N2 O2 S ' _chemical_formula_weight 272.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+3/4, -y+5/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+5/4, -y+3/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+5/4, -y+5/4, z+1/4' _cell_length_a 20.173(6) _cell_length_b 51.635(14) _cell_length_c 5.5236(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5754(3) _cell_formula_units_Z 16 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2274 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23149 _diffrn_reflns_av_R_equivalents 0.1602 _diffrn_reflns_av_sigmaI/netI 0.1510 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -66 _diffrn_reflns_limit_k_max 66 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.74 _reflns_number_total 2787 _reflns_number_gt 1052 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_number_reflns 3387 _refine_ls_number_parameters 183 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2406 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.2192 _refine_ls_wR_factor_gt 0.1652 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.002 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 0.36889(11) 0.04007(4) 0.8174(6) 0.1129(10) Uani 1 1 d . . . N121 N 0.4382(3) 0.0972(2) 1.2059(13) 0.112(2) Uani 1 1 d . . . H121 H 0.4616 0.1031 1.3237 0.135 Uiso 1 1 calc R . . O18 O 0.2865(3) 0.16348(12) 0.4388(14) 0.136(3) Uani 1 1 d . . . O81 O 0.2632(2) 0.12390(13) 0.3275(11) 0.1081(19) Uani 1 1 d . . . C123 C 0.4280(4) 0.0717(2) 1.151(2) 0.118(3) Uani 1 1 d . . . H123 H 0.4457 0.0580 1.2386 0.141 Uiso 1 1 calc R . . N92 N 0.2914(3) 0.14005(16) 0.4628(14) 0.090(2) Uani 1 1 d . . . C1 C 0.2829(3) 0.03885(12) 0.8569(17) 0.077(2) Uani 1 1 d . . . C1# C 0.1444(4) 0.03059(15) 0.914(3) 0.113(4) Uani 1 1 d . . . H1 H 0.1343 0.0456 0.8119 0.135 Uiso 1 1 d R . . C107 C 0.3310(3) 0.13019(15) 0.6589(15) 0.0688(18) Uani 1 1 d . . . C108 C 0.3355(3) 0.10383(13) 0.6884(14) 0.0681(18) Uani 1 1 d . . . H108 H 0.3139 0.0925 0.5838 0.082 Uiso 1 1 calc R . . C109 C 0.3732(3) 0.09470(13) 0.8779(12) 0.0584(16) Uani 1 1 d . . . C110 C 0.3627(4) 0.14712(14) 0.820(2) 0.096(3) Uani 1 1 d . . . H110 H 0.3582 0.1649 0.7978 0.116 Uiso 1 1 calc R . . C111 C 0.3997(3) 0.1383(2) 1.0079(18) 0.099(3) Uani 1 1 d . . . H111 H 0.4212 0.1497 1.1122 0.118 Uiso 1 1 calc R . . C112 C 0.3882(3) 0.06900(15) 0.9513(18) 0.090(3) Uani 1 1 d . . . C113 C 0.2466(7) 0.02466(16) 0.691(2) 0.120(3) Uani 1 1 d . . . H113 H 0.2678 0.0174 0.5581 0.144 Uiso 1 1 calc R . . C114 C 0.2492(3) 0.04860(12) 1.0502(19) 0.088(2) Uani 1 1 d . . . H114 H 0.2724 0.0577 1.1682 0.106 Uiso 1 1 calc R . . C115 C 0.1812(4) 0.04539(13) 1.0768(19) 0.096(2) Uani 1 1 d . . . H115 H 0.1598 0.0533 1.2061 0.115 Uiso 1 1 calc R . . C116 C 0.0693(3) 0.02601(15) 0.954(3) 0.175(6) Uani 1 1 d . . . H11A H 0.0600 0.0078 0.9446 0.262 Uiso 1 1 calc R . . H11B H 0.0446 0.0350 0.8322 0.262 Uiso 1 1 calc R . . H11C H 0.0568 0.0323 1.1114 0.262 Uiso 1 1 calc R . . C117 C 0.1790(7) 0.02111(17) 0.722(3) 0.134(4) Uani 1 1 d . . . H117 H 0.1561 0.0118 0.6049 0.161 Uiso 1 1 calc R . . C118 C 0.4044(3) 0.1117(2) 1.0387(17) 0.080(2) 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 S1 0.1103(14) 0.0978(13) 0.131(2) 0.0108(16) 0.0498(16) 0.0217(10) N121 0.052(4) 0.236(9) 0.049(4) 0.003(6) 0.000(3) 0.010(5) O18 0.115(4) 0.129(4) 0.164(7) 0.049(5) 0.057(4) 0.036(3) O81 0.072(3) 0.168(5) 0.084(4) 0.040(5) 0.019(3) 0.019(3) C123 0.079(6) 0.165(9) 0.109(10) 0.032(8) 0.030(6) 0.030(6) N92 0.059(4) 0.114(6) 0.096(7) 0.020(5) 0.049(5) 0.013(4) C1 0.092(4) 0.063(3) 0.076(6) 0.000(5) 0.015(5) 0.007(3) C1# 0.109(7) 0.059(4) 0.169(11) 0.003(6) -0.049(7) 0.019(4) C107 0.048(4) 0.091(5) 0.067(5) 0.004(5) 0.015(4) 0.004(3) C108 0.047(3) 0.089(5) 0.069(5) -0.001(4) 0.021(4) -0.005(3) C109 0.041(3) 0.096(5) 0.038(4) 0.000(4) 0.013(3) 0.001(3) C110 0.070(5) 0.095(5) 0.124(8) -0.014(7) 0.066(6) -0.014(4) C111 0.047(4) 0.164(9) 0.085(7) -0.052(7) 0.028(4) -0.032(4) C112 0.058(4) 0.121(7) 0.090(7) 0.019(6) 0.027(4) -0.001(4) C113 0.172(9) 0.093(6) 0.095(7) -0.012(6) -0.012(8) 0.009(6) C114 0.074(5) 0.088(4) 0.103(7) -0.003(6) 0.006(5) 0.001(3) C115 0.097(6) 0.095(5) 0.097(7) -0.010(6) -0.011(6) 0.001(4) C116 0.089(6) 0.128(6) 0.31(2) -0.005(9) -0.076(8) -0.005(4) C117 0.167(10) 0.089(6) 0.147(12) -0.029(7) -0.061(10) 0.014(7) C118 0.042(4) 0.131(6) 0.066(6) -0.024(7) 0.026(4) -0.020(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C112 1.712(9) . ? S1 C1 1.750(7) . ? N121 C123 1.367(10) . ? N121 C118 1.370(10) . ? N121 H121 0.8600 . ? O18 N92 1.221(7) . ? O81 N92 1.257(8) . ? C123 C112 1.373(12) . ? C123 H123 0.9300 . ? N92 C107 1.438(10) . ? C1 C114 1.362(11) . ? C1 C113 1.381(12) . ? C1# C117 1.363(14) . ? C1# C115 1.393(12) . ? C1# C116 1.549(10) . ? C1# H1 0.9803 . ? C107 C108 1.374(8) . ? C107 C110 1.402(11) . ? C108 C109 1.377(9) . ? C108 H108 0.9300 . ? C109 C118 1.398(9) . ? C109 C112 1.420(9) . ? C110 C111 1.357(11) . ? C110 H110 0.9300 . ? C111 C118 1.387(10) . ? C111 H111 0.9300 . ? C113 C117 1.386(12) . ? C113 H113 0.9300 . ? C114 C115 1.388(9) . ? C114 H114 0.9300 . ? C115 H115 0.9300 . ? C116 H11A 0.9600 . ? C116 H11B 0.9600 . ? C116 H11C 0.9600 . ? C117 H117 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C112 S1 C1 101.7(4) . . ? C123 N121 C118 107.6(8) . . ? C123 N121 H121 126.2 . . ? C118 N121 H121 126.2 . . ? N121 C123 C112 111.3(9) . . ? N121 C123 H123 124.3 . . ? C112 C123 H123 124.3 . . ? O18 N92 O81 123.8(8) . . ? O18 N92 C107 118.5(8) . . ? O81 N92 C107 117.7(7) . . ? C114 C1 C113 116.8(7) . . ? C114 C1 S1 125.4(7) . . ? C113 C1 S1 117.5(8) . . ? C117 C1# C115 115.2(8) . . ? C117 C1# C116 123.9(12) . . ? C115 C1# C116 120.9(11) . . ? C117 C1# H1 86.5 . . ? C115 C1# H1 92.8 . . ? C116 C1# H1 90.0 . . ? C108 C107 C110 120.8(7) . . ? C108 C107 N92 118.5(7) . . ? C110 C107 N92 120.7(8) . . ? C107 C108 C109 117.8(6) . . ? C107 C108 H108 121.1 . . ? C109 C108 H108 121.1 . . ? C108 C109 C118 121.0(7) . . ? C108 C109 C112 130.9(7) . . ? C118 C109 C112 108.1(7) . . ? C111 C110 C107 121.8(7) . . ? C111 C110 H110 119.1 . . ? C107 C110 H110 119.1 . . ? C110 C111 C118 117.6(8) . . ? C110 C111 H111 121.2 . . ? C118 C111 H111 121.2 . . ? C123 C112 C109 105.0(8) . . ? C123 C112 S1 124.7(9) . . ? C109 C112 S1 130.1(8) . . ? C1 C113 C117 120.7(10) . . ? C1 C113 H113 119.6 . . ? C117 C113 H113 119.6 . . ? C1 C114 C115 122.1(8) . . ? C1 C114 H114 119.0 . . ? C115 C114 H114 119.0 . . ? C114 C115 C1# 121.6(9) . . ? C114 C115 H115 119.2 . . ? C1# C115 H115 119.2 . . ? C1# C116 H11A 109.5 . . ? C1# C116 H11B 109.5 . . ? H11A C116 H11B 109.5 . . ? C1# C116 H11C 109.5 . . ? H11A C116 H11C 109.5 . . ? H11B C116 H11C 109.5 . . ? C1# C117 C113 123.4(10) . . ? C1# C117 H117 118.3 . . ? C113 C117 H117 118.3 . . ? N121 C118 C111 131.0(10) . . ? N121 C118 C109 108.0(8) . . ? C111 C118 C109 120.9(9) . . ? 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 C118 N121 C123 C112 0.1(9) . . . . ? C112 S1 C1 C114 -33.5(7) . . . . ? C112 S1 C1 C113 153.2(7) . . . . ? O18 N92 C107 C108 178.8(6) . . . . ? O81 N92 C107 C108 -0.3(8) . . . . ? O18 N92 C107 C110 0.6(9) . . . . ? O81 N92 C107 C110 -178.6(6) . . . . ? C110 C107 C108 C109 -1.3(8) . . . . ? N92 C107 C108 C109 -179.6(5) . . . . ? C107 C108 C109 C118 1.7(8) . . . . ? C107 C108 C109 C112 -178.7(6) . . . . ? C108 C107 C110 C111 1.1(10) . . . . ? N92 C107 C110 C111 179.3(6) . . . . ? C107 C110 C111 C118 -1.2(10) . . . . ? N121 C123 C112 C109 0.3(8) . . . . ? N121 C123 C112 S1 175.6(5) . . . . ? C108 C109 C112 C123 179.8(6) . . . . ? C118 C109 C112 C123 -0.5(7) . . . . ? C108 C109 C112 S1 4.8(10) . . . . ? C118 C109 C112 S1 -175.5(5) . . . . ? C1 S1 C112 C123 117.2(7) . . . . ? C1 S1 C112 C109 -68.7(7) . . . . ? C114 C1 C113 C117 1.0(12) . . . . ? S1 C1 C113 C117 174.8(7) . . . . ? C113 C1 C114 C115 -2.4(10) . . . . ? S1 C1 C114 C115 -175.6(6) . . . . ? C1 C114 C115 C1# 4.1(11) . . . . ? C117 C1# C115 C114 -4.1(12) . . . . ? C116 C1# C115 C114 176.7(7) . . . . ? C115 C1# C117 C113 2.9(14) . . . . ? C116 C1# C117 C113 -178.0(8) . . . . ? C1 C113 C117 C1# -1.4(14) . . . . ? C123 N121 C118 C111 -178.0(7) . . . . ? C123 N121 C118 C109 -0.4(8) . . . . ? C110 C111 C118 N121 178.9(6) . . . . ? C110 C111 C118 C109 1.5(9) . . . . ? C108 C109 C118 N121 -179.7(5) . . . . ? C112 C109 C118 N121 0.5(6) . . . . ? C108 C109 C118 C111 -1.8(9) . . . . ? C112 C109 C118 C111 178.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.74 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.176 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 953902'