# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Anita Maguire' _publ_contact_author_email A.MAGUIRE@UCC.IE _publ_section_title ; Does intermolecular S=O.H-C-S=O hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state? ; loop_ _publ_author_name 'Anita Maguire' 'Nicolas Brondel' 'Simon Coles' 'Kevin S. Eccles' 'Curtis J. Elcoate' 'Simon Lawrence' ; K.N.Lehane ; 'Edmond J. A. Moynihan' # Attachment 'C000371A.cif' #===================================================================== data_compound_01 _database_code_depnum_ccdc_archive 'CCDC 759274' #TrackingRef 'C000371A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 Br S' _chemical_formula_sum 'C13 H11 Br S' _chemical_formula_weight 279.19 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 5.6004(3) _cell_length_b 13.8743(7) _cell_length_c 15.1686(9) _cell_angle_alpha 93.515(2) _cell_angle_beta 90.117(2) _cell_angle_gamma 93.332(3) _cell_volume 1174.40(11) _cell_formula_units_Z 4 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 20587 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 3.640 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.747 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -1 1 1 reflection has been omitted due to the beamstop. ; _diffrn_ambient_temperature 240(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 10468 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5295 _reflns_number_gt 3738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97, PLATON' _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^)+(0.0887P)^2^+6.2729P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0070(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5295 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1112 _refine_ls_R_factor_gt 0.0786 _refine_ls_wR_factor_ref 0.2224 _refine_ls_wR_factor_gt 0.2028 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.47086(16) 0.41332(6) 0.87295(7) 0.0593(3) Uani 1 1 d . . . C1 C 0.4356(12) 0.2770(5) 0.8823(4) 0.0361(14) Uani 1 1 d . . . C2 C 0.2416(12) 0.2387(5) 0.9277(5) 0.0401(15) Uani 1 1 d . . . H2 H 0.1308 0.2794 0.9546 0.048 Uiso 1 1 calc R . . C3 C 0.2141(11) 0.1401(5) 0.9326(4) 0.0371(14) Uani 1 1 d . . . H3 H 0.0835 0.1135 0.9637 0.045 Uiso 1 1 calc R . . C4 C 0.3757(11) 0.0787(5) 0.8926(4) 0.0356(14) Uani 1 1 d . . . C5 C 0.5673(11) 0.1199(5) 0.8476(4) 0.0364(14) Uani 1 1 d . . . H5 H 0.6777 0.0795 0.8200 0.044 Uiso 1 1 calc R . . C6 C 0.5996(12) 0.2186(5) 0.8422(5) 0.0375(14) Uani 1 1 d . . . H6 H 0.7309 0.2456 0.8118 0.045 Uiso 1 1 calc R . . C7 C 0.3467(12) -0.0297(5) 0.8989(5) 0.0384(15) Uani 1 1 d . . . H7A H 0.3380 -0.0453 0.9610 0.046 Uiso 1 1 calc R . . H7B H 0.4843 -0.0604 0.8720 0.046 Uiso 1 1 calc R . . S8 S 0.0735(3) -0.07408(12) 0.84131(11) 0.0342(4) Uani 1 1 d . . . C9 C 0.0588(11) -0.1991(5) 0.8590(4) 0.0315(13) Uani 1 1 d . . . C10 C -0.1413(11) -0.2528(5) 0.8239(4) 0.0362(14) Uani 1 1 d . . . H10 H -0.2597 -0.2213 0.7946 0.043 Uiso 1 1 calc R . . C11 C -0.1681(12) -0.3518(5) 0.8316(5) 0.0422(16) Uani 1 1 d . . . H11 H -0.3026 -0.3871 0.8067 0.051 Uiso 1 1 calc R . . C12 C 0.0045(14) -0.3994(5) 0.8762(5) 0.0469(17) Uani 1 1 d . . . H12 H -0.0136 -0.4665 0.8823 0.056 Uiso 1 1 calc R . . C13 C 0.2035(13) -0.3457(5) 0.9114(5) 0.0439(16) Uani 1 1 d . . . H13 H 0.3215 -0.3769 0.9411 0.053 Uiso 1 1 calc R . . C14 C 0.2302(11) -0.2468(5) 0.9034(4) 0.0350(14) Uani 1 1 d . . . H14 H 0.3652 -0.2115 0.9280 0.042 Uiso 1 1 calc R . . Br21 Br 0.96346(18) 0.41956(6) 0.65676(7) 0.0629(3) Uani 1 1 d . . . C21 C 0.9318(12) 0.2829(5) 0.6383(5) 0.0380(15) Uani 1 1 d . . . C22 C 0.7387(13) 0.2418(5) 0.5881(5) 0.0411(15) Uani 1 1 d . . . H22 H 0.6282 0.2805 0.5626 0.049 Uiso 1 1 calc R . . C23 C 0.7161(12) 0.1412(5) 0.5770(4) 0.0406(16) Uani 1 1 d . . . H23 H 0.5863 0.1120 0.5439 0.049 Uiso 1 1 calc R . . C24 C 0.8778(11) 0.0828(5) 0.6131(4) 0.0318(13) Uani 1 1 d . . . C25 C 1.0708(12) 0.1269(5) 0.6626(4) 0.0374(14) Uani 1 1 d . . . H25 H 1.1824 0.0886 0.6880 0.045 Uiso 1 1 calc R . . C26 C 1.0974(12) 0.2276(5) 0.6744(4) 0.0402(15) Uani 1 1 d . . . H26 H 1.2278 0.2572 0.7069 0.048 Uiso 1 1 calc R . . C27 C 0.8498(12) -0.0254(5) 0.6006(5) 0.0386(15) Uani 1 1 d . . . H27A H 0.9873 -0.0540 0.6268 0.046 Uiso 1 1 calc R . . H27B H 0.8442 -0.0450 0.5375 0.046 Uiso 1 1 calc R . . S28 S 0.5779(3) -0.06834(12) 0.65274(11) 0.0352(4) Uani 1 1 d . . . C29 C 0.5630(11) -0.1945(5) 0.6263(4) 0.0329(13) Uani 1 1 d . . . C30 C 0.3601(12) -0.2451(5) 0.6570(4) 0.0375(14) Uani 1 1 d . . . H30 H 0.2412 -0.2117 0.6875 0.045 Uiso 1 1 calc R . . C31 C 0.3346(13) -0.3447(5) 0.6424(5) 0.0438(16) Uani 1 1 d . . . H31 H 0.1988 -0.3786 0.6638 0.053 Uiso 1 1 calc R . . C32 C 0.5064(14) -0.3948(5) 0.5967(5) 0.0433(16) Uani 1 1 d . . . H32 H 0.4891 -0.4625 0.5875 0.052 Uiso 1 1 calc R . . C33 C 0.7032(13) -0.3441(5) 0.5649(5) 0.0446(17) Uani 1 1 d . . . H33 H 0.8195 -0.3776 0.5330 0.053 Uiso 1 1 calc R . . C34 C 0.7329(12) -0.2451(5) 0.5788(4) 0.0380(15) Uani 1 1 d . . . H34 H 0.8681 -0.2118 0.5563 0.046 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 Br1 0.0690(6) 0.0330(4) 0.0765(6) 0.0099(4) -0.0036(4) -0.0003(3) C1 0.039(4) 0.033(3) 0.036(3) 0.000(3) -0.006(3) 0.002(3) C2 0.037(4) 0.039(4) 0.044(4) -0.005(3) 0.002(3) 0.002(3) C3 0.031(3) 0.043(4) 0.036(3) -0.001(3) 0.004(3) -0.001(3) C4 0.033(3) 0.038(4) 0.036(3) 0.006(3) -0.004(3) -0.001(3) C5 0.031(3) 0.040(4) 0.038(4) -0.005(3) -0.001(3) 0.005(3) C6 0.031(3) 0.038(4) 0.043(4) 0.005(3) 0.002(3) 0.001(3) C7 0.037(3) 0.035(4) 0.043(4) 0.004(3) -0.011(3) -0.001(3) S8 0.0336(8) 0.0322(8) 0.0369(9) 0.0046(6) -0.0056(6) 0.0018(6) C9 0.029(3) 0.033(3) 0.032(3) -0.002(2) 0.005(2) 0.004(2) C10 0.031(3) 0.046(4) 0.031(3) 0.001(3) -0.003(2) 0.001(3) C11 0.036(4) 0.043(4) 0.045(4) -0.003(3) -0.004(3) -0.009(3) C12 0.052(4) 0.035(4) 0.052(4) -0.005(3) 0.001(3) -0.001(3) C13 0.040(4) 0.037(4) 0.055(4) 0.002(3) 0.000(3) 0.009(3) C14 0.033(3) 0.034(3) 0.038(3) -0.004(3) -0.003(3) 0.003(3) Br21 0.0778(6) 0.0351(5) 0.0740(6) -0.0056(4) 0.0086(4) -0.0027(4) C21 0.039(4) 0.030(3) 0.044(4) -0.002(3) 0.010(3) -0.003(3) C22 0.042(4) 0.044(4) 0.037(4) 0.008(3) -0.008(3) 0.004(3) C23 0.039(4) 0.046(4) 0.037(4) 0.005(3) -0.014(3) -0.004(3) C24 0.030(3) 0.039(3) 0.027(3) 0.006(2) 0.006(2) 0.000(2) C25 0.033(3) 0.043(4) 0.037(4) 0.003(3) -0.001(3) 0.005(3) C26 0.034(3) 0.052(4) 0.034(3) 0.001(3) -0.003(3) -0.004(3) C27 0.036(3) 0.037(4) 0.043(4) 0.007(3) 0.008(3) 0.000(3) S28 0.0334(8) 0.0329(8) 0.0388(9) -0.0007(6) 0.0064(6) -0.0001(6) C29 0.034(3) 0.034(3) 0.030(3) 0.000(2) -0.005(2) -0.002(2) C30 0.039(4) 0.043(4) 0.030(3) 0.002(3) 0.001(3) 0.000(3) C31 0.045(4) 0.039(4) 0.047(4) 0.010(3) 0.001(3) -0.007(3) C32 0.055(4) 0.026(3) 0.049(4) 0.004(3) -0.001(3) 0.002(3) C33 0.039(4) 0.043(4) 0.052(4) -0.004(3) 0.001(3) 0.009(3) C34 0.032(3) 0.042(4) 0.041(4) 0.006(3) 0.006(3) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.904(7) . ? C1 C6 1.378(10) . ? C1 C2 1.384(10) . ? C2 C3 1.375(10) . ? C2 H2 0.9400 . ? C3 C4 1.393(9) . ? C3 H3 0.9400 . ? C4 C5 1.387(9) . ? C4 C7 1.512(9) . ? C5 C6 1.379(9) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C7 S8 1.817(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? S8 C9 1.769(7) . ? C9 C14 1.392(9) . ? C9 C10 1.395(9) . ? C10 C11 1.386(10) . ? C10 H10 0.9400 . ? C11 C12 1.399(11) . ? C11 H11 0.9400 . ? C12 C13 1.391(10) . ? C12 H12 0.9400 . ? C13 C14 1.385(10) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? Br21 C21 1.898(7) . ? C21 C26 1.372(10) . ? C21 C22 1.395(10) . ? C22 C23 1.394(10) . ? C22 H22 0.9400 . ? C23 C24 1.383(9) . ? C23 H23 0.9400 . ? C24 C25 1.404(9) . ? C24 C27 1.500(9) . ? C25 C26 1.396(10) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 S28 1.804(7) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? S28 C29 1.768(7) . ? C29 C34 1.392(9) . ? C29 C30 1.397(9) . ? C30 C31 1.385(10) . ? C30 H30 0.9400 . ? C31 C32 1.382(11) . ? C31 H31 0.9400 . ? C32 C33 1.378(10) . ? C32 H32 0.9400 . ? C33 C34 1.376(10) . ? C33 H33 0.9400 . ? C34 H34 0.9400 . ? 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 121.5(6) . . ? C6 C1 Br1 119.5(5) . . ? C2 C1 Br1 119.0(5) . . ? C3 C2 C1 118.7(6) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 121.3(6) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 118.1(6) . . ? C5 C4 C7 120.5(6) . . ? C3 C4 C7 121.3(6) . . ? C6 C5 C4 121.6(6) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C1 C6 C5 118.7(6) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C4 C7 S8 108.6(4) . . ? C4 C7 H7A 110.0 . . ? S8 C7 H7A 110.0 . . ? C4 C7 H7B 110.0 . . ? S8 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? C9 S8 C7 103.0(3) . . ? C14 C9 C10 118.7(6) . . ? C14 C9 S8 125.3(5) . . ? C10 C9 S8 116.0(5) . . ? C11 C10 C9 120.9(6) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 120.2(6) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 118.7(7) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C14 C13 C12 120.9(7) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C9 120.5(6) . . ? C13 C14 H14 119.7 . . ? C9 C14 H14 119.7 . . ? C26 C21 C22 122.0(6) . . ? C26 C21 Br21 119.6(5) . . ? C22 C21 Br21 118.4(5) . . ? C23 C22 C21 117.4(6) . . ? C23 C22 H22 121.3 . . ? C21 C22 H22 121.3 . . ? C24 C23 C22 122.3(6) . . ? C24 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? C23 C24 C25 118.5(6) . . ? C23 C24 C27 121.5(6) . . ? C25 C24 C27 120.0(6) . . ? C26 C25 C24 120.2(6) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C21 C26 C25 119.5(6) . . ? C21 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C24 C27 S28 109.7(5) . . ? C24 C27 H27A 109.7 . . ? S28 C27 H27A 109.7 . . ? C24 C27 H27B 109.7 . . ? S28 C27 H27B 109.7 . . ? H27A C27 H27B 108.2 . . ? C29 S28 C27 103.9(3) . . ? C34 C29 C30 119.0(6) . . ? C34 C29 S28 125.8(5) . . ? C30 C29 S28 115.2(5) . . ? C31 C30 C29 119.9(6) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C32 C31 C30 120.8(7) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C33 C32 C31 119.0(7) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C34 C33 C32 121.3(7) . . ? C34 C33 H33 119.4 . . ? C32 C33 H33 119.4 . . ? C33 C34 C29 120.0(6) . . ? C33 C34 H34 120.0 . . ? C29 C34 H34 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.2(10) . . . . ? Br1 C1 C2 C3 178.6(5) . . . . ? C1 C2 C3 C4 -0.5(10) . . . . ? C2 C3 C4 C5 0.3(10) . . . . ? C2 C3 C4 C7 179.4(6) . . . . ? C3 C4 C5 C6 0.2(10) . . . . ? C7 C4 C5 C6 -178.9(6) . . . . ? C2 C1 C6 C5 0.3(10) . . . . ? Br1 C1 C6 C5 -178.2(5) . . . . ? C4 C5 C6 C1 -0.5(10) . . . . ? C5 C4 C7 S8 -115.8(6) . . . . ? C3 C4 C7 S8 65.1(7) . . . . ? C4 C7 S8 C9 -177.4(5) . . . . ? C7 S8 C9 C14 -2.8(6) . . . . ? C7 S8 C9 C10 178.0(5) . . . . ? C14 C9 C10 C11 -1.1(10) . . . . ? S8 C9 C10 C11 178.2(5) . . . . ? C9 C10 C11 C12 1.1(11) . . . . ? C10 C11 C12 C13 -0.8(11) . . . . ? C11 C12 C13 C14 0.6(11) . . . . ? C12 C13 C14 C9 -0.6(11) . . . . ? C10 C9 C14 C13 0.8(10) . . . . ? S8 C9 C14 C13 -178.3(5) . . . . ? C26 C21 C22 C23 1.3(10) . . . . ? Br21 C21 C22 C23 -178.6(5) . . . . ? C21 C22 C23 C24 -0.7(11) . . . . ? C22 C23 C24 C25 0.2(10) . . . . ? C22 C23 C24 C27 179.8(6) . . . . ? C23 C24 C25 C26 -0.3(9) . . . . ? C27 C24 C25 C26 -179.9(6) . . . . ? C22 C21 C26 C25 -1.4(10) . . . . ? Br21 C21 C26 C25 178.5(5) . . . . ? C24 C25 C26 C21 0.9(10) . . . . ? C23 C24 C27 S28 -63.8(7) . . . . ? C25 C24 C27 S28 115.8(6) . . . . ? C24 C27 S28 C29 176.5(5) . . . . ? C27 S28 C29 C34 2.2(7) . . . . ? C27 S28 C29 C30 -177.8(5) . . . . ? C34 C29 C30 C31 2.1(10) . . . . ? S28 C29 C30 C31 -177.9(5) . . . . ? C29 C30 C31 C32 -0.8(10) . . . . ? C30 C31 C32 C33 -0.7(11) . . . . ? C31 C32 C33 C34 0.9(11) . . . . ? C32 C33 C34 C29 0.4(11) . . . . ? C30 C29 C34 C33 -1.8(10) . . . . ? S28 C29 C34 C33 178.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.907 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.142 #===END============================================================== data_compound_02 _database_code_depnum_ccdc_archive 'CCDC 759275' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 O2 S' _chemical_formula_sum 'C15 H16 O2 S' _chemical_formula_weight 260.34 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' 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 'P 21/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 30.458(3) _cell_length_b 5.4558(6) _cell_length_c 8.0849(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.494(7) _cell_angle_gamma 90.00 _cell_volume 1343.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.46 _cell_measurement_theta_max 15.32 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius MACH3' _diffrn_measurement_method '\w-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3712 _diffrn_reflns_av_R_equivalents 0.0805 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.51 _reflns_number_total 2500 _reflns_number_gt 1702 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'PLATON (Spek, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0357P)^2^+0.6900P] 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 2500 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 C1 C 0.46535(8) -0.2489(6) 0.4149(4) 0.0748(8) Uani 1 1 d . . . H1A H 0.4521 -0.2567 0.5220 0.112 Uiso 1 1 calc R . . H1B H 0.4967 -0.2392 0.4274 0.112 Uiso 1 1 calc R . . H1C H 0.4578 -0.3932 0.3529 0.112 Uiso 1 1 calc R . . O2 O 0.44985(5) -0.0384(4) 0.3296(2) 0.0671(5) Uani 1 1 d . . . C3 C 0.40572(7) -0.0259(4) 0.2922(3) 0.0481(6) Uani 1 1 d . . . C4 C 0.39295(8) 0.1698(5) 0.1937(3) 0.0574(6) Uani 1 1 d . . . H4 H 0.4139 0.2807 0.1568 0.069 Uiso 1 1 calc R . . C5 C 0.34961(8) 0.2011(4) 0.1501(3) 0.0530(6) Uani 1 1 d . . . H5 H 0.3414 0.3349 0.0855 0.064 Uiso 1 1 calc R . . C6 C 0.31780(7) 0.0355(4) 0.2012(3) 0.0447(5) Uani 1 1 d . . . C7 C 0.33103(8) -0.1608(4) 0.2982(3) 0.0519(6) Uani 1 1 d . . . H7 H 0.3103 -0.2744 0.3330 0.062 Uiso 1 1 calc R . . C8 C 0.37476(7) -0.1908(4) 0.3443(3) 0.0504(6) Uani 1 1 d . . . H8 H 0.3830 -0.3226 0.4105 0.060 Uiso 1 1 calc R . . S9 S 0.26322(2) 0.08675(14) 0.13171(8) 0.0624(2) Uani 1 1 d . . . C10 C 0.23047(7) -0.0766(5) 0.2805(3) 0.0576(6) Uani 1 1 d . . . H10A H 0.2375 -0.2500 0.2776 0.069 Uiso 1 1 calc R . . H10B H 0.2366 -0.0157 0.3911 0.069 Uiso 1 1 calc R . . C11 C 0.18272(7) -0.0376(4) 0.2369(3) 0.0469(6) Uani 1 1 d . . . C12 C 0.15945(8) 0.1612(4) 0.2954(3) 0.0510(6) Uani 1 1 d . . . H12 H 0.1735 0.2738 0.3641 0.061 Uiso 1 1 calc R . . C13 C 0.11567(8) 0.1968(4) 0.2542(3) 0.0494(6) Uani 1 1 d . . . H13 H 0.1006 0.3315 0.2955 0.059 Uiso 1 1 calc R . . C14 C 0.09448(7) 0.0311(4) 0.1514(2) 0.0443(5) Uani 1 1 d . . . C15 C 0.11738(8) -0.1677(4) 0.0907(3) 0.0500(6) Uani 1 1 d . . . H15 H 0.1034 -0.2787 0.0205 0.060 Uiso 1 1 calc R . . C16 C 0.16094(8) -0.2020(5) 0.1338(3) 0.0507(6) Uani 1 1 d . . . H16 H 0.1759 -0.3373 0.0931 0.061 Uiso 1 1 calc R . . O17 O 0.05130(5) 0.0488(3) 0.1008(2) 0.0607(5) Uani 1 1 d . . . C18 C 0.02695(8) 0.2567(6) 0.1545(4) 0.0713(8) Uani 1 1 d . . . H18A H 0.0257 0.2575 0.2731 0.107 Uiso 1 1 calc R . . H18B H -0.0023 0.2490 0.1095 0.107 Uiso 1 1 calc R . . H18C H 0.0411 0.4037 0.1171 0.107 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 C1 0.0489(15) 0.093(2) 0.0821(19) 0.0086(17) -0.0123(14) 0.0089(15) O2 0.0435(10) 0.0783(13) 0.0795(12) 0.0080(11) -0.0060(8) -0.0047(9) C3 0.0427(12) 0.0551(15) 0.0463(12) -0.0066(11) 0.0003(10) 0.0003(11) C4 0.0522(15) 0.0532(16) 0.0669(15) 0.0068(13) 0.0035(12) -0.0118(12) C5 0.0557(15) 0.0446(14) 0.0587(14) 0.0090(12) -0.0007(11) -0.0015(12) C6 0.0459(12) 0.0458(13) 0.0425(11) -0.0007(11) 0.0027(9) 0.0005(11) C7 0.0459(13) 0.0494(15) 0.0604(14) 0.0115(12) 0.0016(11) -0.0037(11) C8 0.0492(14) 0.0488(14) 0.0532(13) 0.0070(11) 0.0009(10) 0.0031(11) S9 0.0489(4) 0.0763(5) 0.0619(4) 0.0236(4) -0.0022(3) 0.0032(3) C10 0.0489(14) 0.0661(17) 0.0579(14) 0.0124(13) -0.0045(11) -0.0005(13) C11 0.0474(13) 0.0519(14) 0.0413(12) 0.0086(11) -0.0002(10) -0.0032(11) C12 0.0557(15) 0.0492(15) 0.0479(13) -0.0039(11) -0.0100(10) -0.0046(12) C13 0.0549(14) 0.0455(14) 0.0477(13) -0.0012(11) -0.0004(10) 0.0054(11) C14 0.0437(12) 0.0496(14) 0.0394(11) 0.0052(10) -0.0006(9) -0.0049(11) C15 0.0514(14) 0.0485(14) 0.0500(13) -0.0089(11) -0.0029(10) -0.0080(11) C16 0.0550(14) 0.0470(14) 0.0502(13) -0.0016(11) 0.0063(11) 0.0023(12) O17 0.0451(9) 0.0698(12) 0.0672(10) -0.0041(9) -0.0080(8) -0.0006(9) C18 0.0525(16) 0.081(2) 0.0807(18) 0.0044(17) -0.0048(13) 0.0113(15) _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 C1 O2 1.418(3) . ? O2 C3 1.377(3) . ? C3 C8 1.372(3) . ? C3 C4 1.386(3) . ? C4 C5 1.374(3) . ? C5 C6 1.390(3) . ? C6 C7 1.385(3) . ? C6 S9 1.772(2) . ? C7 C8 1.390(3) . ? S9 C10 1.804(2) . ? C10 C11 1.508(3) . ? C11 C12 1.381(3) . ? C11 C16 1.389(3) . ? C12 C13 1.385(3) . ? C13 C14 1.384(3) . ? C14 O17 1.377(2) . ? C14 C15 1.382(3) . ? C15 C16 1.382(3) . ? O17 C18 1.425(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 C3 O2 C1 117.8(2) . . ? C8 C3 O2 124.9(2) . . ? C8 C3 C4 119.4(2) . . ? O2 C3 C4 115.7(2) . . ? C5 C4 C3 120.5(2) . . ? C4 C5 C6 120.9(2) . . ? C7 C6 C5 118.1(2) . . ? C7 C6 S9 124.68(18) . . ? C5 C6 S9 117.22(18) . . ? C6 C7 C8 121.1(2) . . ? C3 C8 C7 120.0(2) . . ? C6 S9 C10 103.48(10) . . ? C11 C10 S9 108.20(15) . . ? C12 C11 C16 117.9(2) . . ? C12 C11 C10 121.8(2) . . ? C16 C11 C10 120.2(2) . . ? C11 C12 C13 121.6(2) . . ? C14 C13 C12 119.7(2) . . ? O17 C14 C15 115.7(2) . . ? O17 C14 C13 124.9(2) . . ? C15 C14 C13 119.5(2) . . ? C16 C15 C14 120.2(2) . . ? C15 C16 C11 121.1(2) . . ? C14 O17 C18 117.63(19) . . ? 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 C3 C8 6.4(3) . . . . ? C1 O2 C3 C4 -173.3(2) . . . . ? C8 C3 C4 C5 0.9(4) . . . . ? O2 C3 C4 C5 -179.4(2) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C4 C5 C6 C7 0.4(3) . . . . ? C4 C5 C6 S9 -177.73(19) . . . . ? C5 C6 C7 C8 0.5(3) . . . . ? S9 C6 C7 C8 178.49(18) . . . . ? O2 C3 C8 C7 -179.6(2) . . . . ? C4 C3 C8 C7 0.0(3) . . . . ? C6 C7 C8 C3 -0.7(4) . . . . ? C7 C6 S9 C10 23.8(2) . . . . ? C5 C6 S9 C10 -158.22(19) . . . . ? C6 S9 C10 C11 177.90(17) . . . . ? S9 C10 C11 C12 -87.4(2) . . . . ? S9 C10 C11 C16 91.8(2) . . . . ? C16 C11 C12 C13 0.4(3) . . . . ? C10 C11 C12 C13 179.6(2) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C12 C13 C14 O17 -179.3(2) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? O17 C14 C15 C16 179.9(2) . . . . ? C13 C14 C15 C16 0.7(3) . . . . ? C14 C15 C16 C11 -0.7(3) . . . . ? C12 C11 C16 C15 0.1(3) . . . . ? C10 C11 C16 C15 -179.1(2) . . . . ? C15 C14 O17 C18 -177.3(2) . . . . ? C13 C14 O17 C18 1.9(3) . . . . ? _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 1.00 _refine_diff_density_max 0.180 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.041 #===END============================================================== data_compound_03 _database_code_depnum_ccdc_archive 'CCDC 759276' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O2 S' _chemical_formula_sum 'C16 H18 O2 S' _chemical_formula_weight 274.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.1016(3) _cell_length_b 5.30912(18) _cell_length_c 16.8806(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.057(3) _cell_angle_gamma 90.00 _cell_volume 720.57(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5965 _cell_measurement_theta_min 5.2857 _cell_measurement_theta_max 67.3730 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 1.951 _exptl_absorpt_correction_T_min 0.63013 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 10.2673 _diffrn_measurement_device_type 'Gemini R Ultra' _diffrn_measurement_method 'thin slice \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6182 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.28 _diffrn_reflns_theta_max 67.49 _reflns_number_total 2485 _reflns_number_gt 2398 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0559P)^2^+0.2354P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unk _refine_ls_abs_structure_Flack 0.42(2) _refine_ls_number_reflns 2485 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 0.69781(7) -0.19084(14) 0.72922(3) 0.04110(18) Uani 1 1 d . . . O2 O 0.78229(18) -0.1894(4) 0.38588(8) 0.0394(4) Uani 1 1 d . . . O3 O 0.72261(18) 0.1165(3) 1.10053(8) 0.0311(3) Uani 1 1 d . . . C4 C 0.7588(2) -0.1711(5) 0.46472(11) 0.0273(4) Uani 1 1 d . . . C5 C 0.7405(2) 0.1128(4) 1.02076(12) 0.0258(4) Uani 1 1 d . . . C6 C 0.8226(3) 0.0710(5) 0.77286(13) 0.0383(6) Uani 1 1 d . . . H6 H 0.7750 0.2289 0.7470 0.046 Uiso 1 1 calc R . . C7 C 0.6687(2) 0.2854(4) 0.96561(11) 0.0296(4) Uani 1 1 d . . . H7 H 0.6009 0.4168 0.9820 0.035 Uiso 1 1 calc R . . C8 C 0.8387(3) -0.0789(4) 0.99591(13) 0.0305(5) Uani 1 1 d . . . H8 H 0.8878 -0.1990 1.0333 0.037 Uiso 1 1 calc R . . C9 C 0.6640(3) 0.0111(4) 0.49610(13) 0.0296(5) Uani 1 1 d . . . H9 H 0.6098 0.1374 0.4625 0.036 Uiso 1 1 calc R . . C10 C 0.8236(3) -0.3564(4) 0.59431(13) 0.0327(5) Uani 1 1 d . . . H10 H 0.8803 -0.4804 0.6279 0.039 Uiso 1 1 calc R . . C11 C 0.6958(3) 0.2661(4) 0.88606(13) 0.0333(5) Uani 1 1 d . . . H11 H 0.6450 0.3846 0.8486 0.040 Uiso 1 1 calc R . . C12 C 0.7275(2) -0.1786(5) 0.62704(11) 0.0294(4) Uani 1 1 d . . . C13 C 0.6214(2) 0.3130(5) 1.12624(11) 0.0337(4) Uani 1 1 d . . . H13A H 0.6669 0.4767 1.1131 0.051 Uiso 1 1 calc R . . H13B H 0.6200 0.3011 1.1841 0.051 Uiso 1 1 calc R . . H13C H 0.5078 0.2962 1.0992 0.051 Uiso 1 1 calc R . . C14 C 0.8390(3) -0.3577(4) 0.51407(13) 0.0318(5) Uani 1 1 d . . . H14 H 0.9034 -0.4838 0.4923 0.038 Uiso 1 1 calc R . . C15 C 0.7941(3) 0.0803(4) 0.86045(13) 0.0328(5) Uani 1 1 d . . . C16 C 0.6485(3) 0.0083(4) 0.57698(13) 0.0323(5) Uani 1 1 d . . . H16 H 0.5838 0.1340 0.5988 0.039 Uiso 1 1 calc R . . C17 C 0.8651(3) -0.0952(4) 0.91608(14) 0.0343(5) Uani 1 1 d . . . H17 H 0.9321 -0.2270 0.8993 0.041 Uiso 1 1 calc R . . C18 C 0.7054(4) -0.0018(6) 0.33313(15) 0.0523(7) Uani 1 1 d . . . H18A H 0.5843 -0.0140 0.3311 0.078 Uiso 1 1 calc R . . H18B H 0.7371 -0.0279 0.2795 0.078 Uiso 1 1 calc R . . H18C H 0.7421 0.1656 0.3525 0.078 Uiso 1 1 calc R . . C19 C 1.0003(3) 0.0591(7) 0.75973(15) 0.0572(8) Uani 1 1 d . . . H19A H 1.0598 0.2037 0.7856 0.086 Uiso 1 1 calc R . . H19B H 1.0087 0.0631 0.7023 0.086 Uiso 1 1 calc R . . H19C H 1.0496 -0.0973 0.7826 0.086 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 0.0451(3) 0.0506(3) 0.0284(3) -0.0005(3) 0.0079(2) -0.0216(3) O2 0.0398(8) 0.0508(9) 0.0288(7) 0.0055(9) 0.0085(6) 0.0127(9) O3 0.0277(7) 0.0393(9) 0.0266(7) 0.0028(6) 0.0046(6) 0.0047(6) C4 0.0226(9) 0.0313(11) 0.0285(9) 0.0025(10) 0.0045(7) -0.0023(9) C5 0.0214(9) 0.0300(10) 0.0264(10) 0.0014(8) 0.0047(7) -0.0046(8) C6 0.0391(13) 0.0443(14) 0.0323(12) -0.0021(10) 0.0082(10) -0.0147(11) C7 0.0311(10) 0.0281(10) 0.0300(9) 0.0017(10) 0.0053(7) -0.0020(10) C8 0.0250(10) 0.0301(10) 0.0361(11) 0.0028(9) 0.0030(8) 0.0010(9) C9 0.0262(10) 0.0290(10) 0.0332(11) 0.0028(9) 0.0020(8) 0.0023(9) C10 0.0316(11) 0.0301(11) 0.0348(12) 0.0075(9) -0.0020(9) -0.0022(9) C11 0.0373(11) 0.0323(12) 0.0301(10) 0.0048(9) 0.0035(8) -0.0069(9) C12 0.0262(9) 0.0361(11) 0.0260(9) 0.0027(11) 0.0038(7) -0.0098(11) C13 0.0277(9) 0.0441(11) 0.0301(9) -0.0046(12) 0.0062(7) 0.0030(11) C14 0.0266(10) 0.0312(11) 0.0373(11) -0.0011(9) 0.0029(9) 0.0035(9) C15 0.0294(11) 0.0387(12) 0.0308(11) -0.0031(9) 0.0060(8) -0.0120(10) C16 0.0277(11) 0.0339(11) 0.0356(12) -0.0057(9) 0.0048(9) 0.0023(9) C17 0.0238(10) 0.0373(11) 0.0432(12) -0.0098(9) 0.0096(9) -0.0048(9) C18 0.0590(17) 0.0680(18) 0.0315(12) 0.0140(13) 0.0116(11) 0.0202(15) C19 0.0415(14) 0.098(2) 0.0335(12) -0.0051(14) 0.0098(11) -0.0268(15) _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 C12 1.7720(19) . ? S1 C6 1.820(2) . ? O2 C4 1.371(2) . ? O2 C18 1.427(3) . ? O3 C5 1.372(2) . ? O3 C13 1.427(3) . ? C4 C9 1.381(3) . ? C4 C14 1.402(3) . ? C5 C7 1.383(3) . ? C5 C8 1.388(3) . ? C6 C19 1.484(4) . ? C6 C15 1.525(3) . ? C7 C11 1.391(3) . ? C8 C17 1.393(3) . ? C9 C16 1.387(3) . ? C10 C14 1.375(3) . ? C10 C12 1.381(3) . ? C11 C15 1.371(3) . ? C12 C16 1.406(3) . ? C15 C17 1.396(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 C12 S1 C6 103.34(10) . . ? C4 O2 C18 117.03(19) . . ? C5 O3 C13 116.29(16) . . ? O2 C4 C9 124.9(2) . . ? O2 C4 C14 114.7(2) . . ? C9 C4 C14 120.43(18) . . ? O3 C5 C7 124.37(19) . . ? O3 C5 C8 116.15(18) . . ? C7 C5 C8 119.48(19) . . ? C19 C6 C15 114.3(2) . . ? C19 C6 S1 114.1(2) . . ? C15 C6 S1 105.94(15) . . ? C5 C7 C11 119.8(2) . . ? C5 C8 C17 120.0(2) . . ? C4 C9 C16 119.49(19) . . ? C14 C10 C12 121.40(19) . . ? C15 C11 C7 121.6(2) . . ? C10 C12 C16 118.67(18) . . ? C10 C12 S1 120.99(17) . . ? C16 C12 S1 120.30(18) . . ? C10 C14 C4 119.4(2) . . ? C11 C15 C17 118.4(2) . . ? C11 C15 C6 119.5(2) . . ? C17 C15 C6 122.1(2) . . ? C9 C16 C12 120.6(2) . . ? C8 C17 C15 120.7(2) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 66.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.378 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.042 #===END============================================================== data_compound_04 _database_code_depnum_ccdc_archive 'CCDC 759277' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O2 S' _chemical_formula_sum 'C16 H18 O2 S' _chemical_formula_weight 274.36 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' 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 'P 21 /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 7.8617(2) _cell_length_b 22.6828(6) _cell_length_c 8.5775(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.3340(10) _cell_angle_gamma 90.00 _cell_volume 1382.48(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2793 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8940 _exptl_absorpt_correction_T_max 0.9556 _exptl_absorpt_process_details 'SADABS V2.10(Sheldrick, G.M., 2003)' _exptl_special_details ; The -1 0 2, -2 1 1, 0 2 0, -1 2 1 and 0 1 1 reflections have been omitted due to the beamstop. The transmission factors above are based on the crystal size, using SHELXL-97. The output from SADABS has a ratio of minimum to maximum apparent transmission of 0.9106. ; _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 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11010 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3068 _reflns_number_gt 2682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0368P)^2^+0.7178P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.025(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3068 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.0202(2) 0.51625(7) 0.2440(2) 0.0272(3) Uani 1 1 d . . . H1A H 0.0951 0.4927 0.2005 0.041 Uiso 1 1 calc R . . H1B H -0.0663 0.5415 0.1514 0.041 Uiso 1 1 calc R . . H1C H -0.0520 0.4900 0.2838 0.041 Uiso 1 1 calc R . . O2 O 0.14262(14) 0.55206(4) 0.38434(12) 0.0234(2) Uani 1 1 d . . . C3 C 0.27562(19) 0.52373(6) 0.52438(17) 0.0180(3) Uani 1 1 d . . . C4 C 0.2995(2) 0.46315(6) 0.53932(19) 0.0229(3) Uani 1 1 d . . . H4 H 0.2208 0.4381 0.4482 0.027 Uiso 1 1 calc R . . C5 C 0.4392(2) 0.43912(6) 0.6882(2) 0.0253(3) Uani 1 1 d . . . H5 H 0.4570 0.3976 0.6975 0.030 Uiso 1 1 calc R . . C6 C 0.5519(2) 0.47493(6) 0.82230(19) 0.0234(3) Uani 1 1 d . . . H6 H 0.6458 0.4581 0.9243 0.028 Uiso 1 1 calc R . . C7 C 0.52794(19) 0.53592(6) 0.80803(18) 0.0196(3) Uani 1 1 d . . . H7 H 0.6055 0.5605 0.9009 0.023 Uiso 1 1 calc R . . C8 C 0.39194(18) 0.56095(6) 0.65956(17) 0.0163(3) Uani 1 1 d . . . S9 S 0.35108(5) 0.637542(14) 0.62330(4) 0.01786(12) Uani 1 1 d . . . C10 C 0.49935(18) 0.67039(6) 0.83083(17) 0.0160(3) Uani 1 1 d . . . H10 H 0.4731 0.6499 0.9214 0.019 Uiso 1 1 calc R . . C11 C 0.4338(2) 0.73460(6) 0.82035(19) 0.0219(3) Uani 1 1 d . . . H11A H 0.5045 0.7540 0.9317 0.033 Uiso 1 1 calc R . . H11B H 0.2992 0.7355 0.7922 0.033 Uiso 1 1 calc R . . H11C H 0.4560 0.7553 0.7305 0.033 Uiso 1 1 calc R . . C12 C 0.70978(18) 0.66706(5) 0.88254(16) 0.0146(3) Uani 1 1 d . . . C13 C 0.78605(19) 0.65995(6) 0.76527(17) 0.0181(3) Uani 1 1 d . . . H13 H 0.7044 0.6573 0.6458 0.022 Uiso 1 1 calc R . . C14 C 0.9800(2) 0.65653(6) 0.81832(19) 0.0214(3) Uani 1 1 d . . . H14 H 1.0301 0.6520 0.7360 0.026 Uiso 1 1 calc R . . C15 C 1.09840(19) 0.65976(6) 0.99251(19) 0.0214(3) Uani 1 1 d . . . H15 H 1.2306 0.6567 1.0298 0.026 Uiso 1 1 calc R . . C16 C 1.02659(19) 0.66735(6) 1.11336(18) 0.0188(3) Uani 1 1 d . . . H16 H 1.1090 0.6695 1.2327 0.023 Uiso 1 1 calc R . . C17 C 0.83293(18) 0.67178(5) 1.05863(17) 0.0151(3) Uani 1 1 d . . . O18 O 0.74835(13) 0.67996(4) 1.16707(12) 0.0192(2) Uani 1 1 d . . . C19 C 0.8690(2) 0.68271(6) 1.34800(17) 0.0207(3) Uani 1 1 d . . . H19A H 0.9384 0.6456 1.3852 0.031 Uiso 1 1 calc R . . H19B H 0.7929 0.6891 1.4120 0.031 Uiso 1 1 calc R . . H19C H 0.9581 0.7154 1.3706 0.031 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 C1 0.0230(7) 0.0296(8) 0.0217(7) -0.0086(6) 0.0025(6) -0.0059(6) O2 0.0198(5) 0.0229(5) 0.0193(5) -0.0051(4) 0.0004(4) -0.0020(4) C3 0.0154(6) 0.0219(7) 0.0176(6) -0.0012(5) 0.0079(5) -0.0015(5) C4 0.0254(7) 0.0209(7) 0.0233(7) -0.0056(6) 0.0112(6) -0.0056(6) C5 0.0320(8) 0.0167(6) 0.0292(8) 0.0007(6) 0.0152(7) -0.0007(6) C6 0.0254(7) 0.0227(7) 0.0216(7) 0.0048(6) 0.0096(6) 0.0009(6) C7 0.0195(7) 0.0206(6) 0.0185(7) 0.0000(5) 0.0080(6) -0.0019(5) C8 0.0156(6) 0.0171(6) 0.0182(6) -0.0013(5) 0.0090(5) -0.0023(5) S9 0.01491(18) 0.01695(17) 0.01584(18) -0.00151(12) 0.00096(13) -0.00008(12) C10 0.0136(6) 0.0180(6) 0.0142(6) -0.0023(5) 0.0039(5) -0.0006(5) C11 0.0179(6) 0.0198(7) 0.0250(7) -0.0029(6) 0.0063(6) 0.0033(5) C12 0.0139(6) 0.0120(6) 0.0164(6) -0.0005(5) 0.0051(5) -0.0007(5) C13 0.0190(6) 0.0182(6) 0.0162(6) -0.0016(5) 0.0068(5) -0.0013(5) C14 0.0213(7) 0.0229(7) 0.0239(7) -0.0030(6) 0.0134(6) -0.0013(6) C15 0.0140(6) 0.0219(7) 0.0281(8) 0.0002(6) 0.0088(6) -0.0009(5) C16 0.0143(6) 0.0199(6) 0.0178(6) 0.0009(5) 0.0027(5) -0.0023(5) C17 0.0157(6) 0.0139(6) 0.0156(6) -0.0003(5) 0.0065(5) -0.0009(5) O18 0.0153(5) 0.0283(5) 0.0124(5) -0.0003(4) 0.0045(4) 0.0007(4) C19 0.0213(7) 0.0251(7) 0.0127(6) -0.0009(5) 0.0045(5) -0.0003(6) _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 C1 O2 1.4295(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C3 1.3690(16) . ? C3 C4 1.3853(19) . ? C3 C8 1.4093(19) . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 C6 1.377(2) . ? C5 H5 0.9500 . ? C6 C7 1.3943(19) . ? C6 H6 0.9500 . ? C7 C8 1.3864(19) . ? C7 H7 0.9500 . ? C8 S9 1.7700(14) . ? S9 C10 1.8185(13) . ? C10 C12 1.5203(18) . ? C10 C11 1.5345(18) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.3833(19) . ? C12 C17 1.4066(18) . ? C13 C14 1.3942(19) . ? C13 H13 0.9500 . ? C14 C15 1.384(2) . ? C14 H14 0.9500 . ? C15 C16 1.387(2) . ? C15 H15 0.9500 . ? C16 C17 1.3917(18) . ? C16 H16 0.9500 . ? C17 O18 1.3679(16) . ? O18 C19 1.4325(15) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O2 C1 117.28(11) . . ? O2 C3 C4 124.69(13) . . ? O2 C3 C8 115.08(12) . . ? C4 C3 C8 120.24(13) . . ? C3 C4 C5 119.75(13) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.59(13) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.84(13) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 120.60(13) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C3 118.96(12) . . ? C7 C8 S9 125.03(10) . . ? C3 C8 S9 116.00(10) . . ? C8 S9 C10 103.77(6) . . ? C12 C10 C11 111.12(11) . . ? C12 C10 S9 115.27(9) . . ? C11 C10 S9 105.84(9) . . ? C12 C10 H10 108.1 . . ? C11 C10 H10 108.1 . . ? S9 C10 H10 108.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 118.45(12) . . ? C13 C12 C10 123.35(12) . . ? C17 C12 C10 118.20(11) . . ? C12 C13 C14 121.53(13) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 119.08(13) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 120.84(13) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C17 119.56(12) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? O18 C17 C16 124.08(12) . . ? O18 C17 C12 115.41(11) . . ? C16 C17 C12 120.51(12) . . ? C17 O18 C19 116.97(10) . . ? O18 C19 H19A 109.5 . . ? O18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C1 O2 C3 C4 0.0(2) . . . . ? C1 O2 C3 C8 -179.65(12) . . . . ? O2 C3 C4 C5 -179.75(13) . . . . ? C8 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 1.1(2) . . . . ? C4 C5 C6 C7 -0.9(2) . . . . ? C5 C6 C7 C8 -0.3(2) . . . . ? C6 C7 C8 C3 1.2(2) . . . . ? C6 C7 C8 S9 -178.43(11) . . . . ? O2 C3 C8 C7 178.62(12) . . . . ? C4 C3 C8 C7 -1.0(2) . . . . ? O2 C3 C8 S9 -1.68(16) . . . . ? C4 C3 C8 S9 178.69(11) . . . . ? C7 C8 S9 C10 -8.08(13) . . . . ? C3 C8 S9 C10 172.25(10) . . . . ? C8 S9 C10 C12 70.40(10) . . . . ? C8 S9 C10 C11 -166.36(9) . . . . ? C11 C10 C12 C13 -98.04(14) . . . . ? S9 C10 C12 C13 22.36(16) . . . . ? C11 C10 C12 C17 81.60(14) . . . . ? S9 C10 C12 C17 -158.00(10) . . . . ? C17 C12 C13 C14 1.00(19) . . . . ? C10 C12 C13 C14 -179.36(12) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C13 C14 C15 C16 -1.1(2) . . . . ? C14 C15 C16 C17 0.0(2) . . . . ? C15 C16 C17 O18 -179.24(12) . . . . ? C15 C16 C17 C12 1.67(19) . . . . ? C13 C12 C17 O18 178.68(11) . . . . ? C10 C12 C17 O18 -0.98(16) . . . . ? C13 C12 C17 C16 -2.15(18) . . . . ? C10 C12 C17 C16 178.19(12) . . . . ? C16 C17 O18 C19 -1.44(18) . . . . ? C12 C17 O18 C19 177.69(11) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.313 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.055 #===END============================================================== data_compound_05 _database_code_depnum_ccdc_archive 'CCDC 759278' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C13 H10 F2 O2 S' _chemical_formula_sum 'C13 H10 F2 O2 S' _chemical_formula_iupac ? _chemical_formula_weight 268.27 _chemical_melting_point ? _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall ' P 2c -2ac' 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 8.7490(9) _cell_length_b 5.3330(5) _cell_length_c 24.881(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1160.9(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1742 _cell_measurement_theta_min 3.2752 _cell_measurement_theta_max 27.1484 _cell_measurement_temperature 100.(2) _exptl_crystal_description Block _exptl_crystal_colour 'clear colourless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs Version 2008/1' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.94 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX DUO' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 3939 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.22 _diffrn_reflns_theta_full 27.22 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _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. ; _reflns_number_total 2355 _reflns_number_gt 2144 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.0718 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_number_reflns 2355 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.2602P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.305 _refine_diff_density_min -0.291 _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 0.05(7) _chemical_absolute_configuration ad 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _computing_data_collection 'Bruker Instrument Service v2009, 7, 0, 0' _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL--97; PLATON' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.30859(5) 0.65369(9) 0.96330(2) 0.01253(11) Uani d . 1 . . O O2 0.31366(14) 0.3857(2) 0.95482(6) 0.0172(2) Uani d . 1 . . O O3 0.16274(13) 0.7771(2) 0.95740(6) 0.0181(2) Uani d . 1 . . C C4 0.3775(2) 0.7188(4) 1.02888(8) 0.0140(4) Uani d . 1 . . C C5 0.3252(2) 0.9300(4) 1.05515(9) 0.0172(5) Uani d . 1 . . H H5 0.253 1.0383 1.0386 0.021 Uiso calc R 1 . . C C6 0.3807(2) 0.9809(5) 1.10667(9) 0.0209(5) Uani d . 1 . . H H6 0.346 1.1232 1.1261 0.025 Uiso calc R 1 . . C C7 0.4866(2) 0.8201(4) 1.12849(8) 0.0194(5) Uani d . 1 . . C C8 0.5391(2) 0.6087(5) 1.10296(9) 0.0193(5) Uani d . 1 . . H H8 0.6118 0.5015 1.1196 0.023 Uiso calc R 1 . . C C9 0.4824(2) 0.5566(4) 1.05191(9) 0.0160(5) Uani d . 1 . . H H9 0.5154 0.4114 1.033 0.019 Uiso calc R 1 . . F F10 0.54281(16) 0.8746(2) 1.17797(5) 0.0277(2) Uani d . 1 . . C C11 0.4444(2) 0.8054(4) 0.92071(8) 0.0136(4) Uani d . 1 . . H H11A 0.4482 0.9866 0.9292 0.016 Uiso calc R 1 . . H H11B 0.5473 0.7337 0.9269 0.016 Uiso calc R 1 . . C C12 0.3992(2) 0.7696(4) 0.86283(8) 0.0132(4) Uani d . 1 . . C C13 0.2961(2) 0.9343(4) 0.83871(10) 0.0174(4) Uani d . 1 . . H H13 0.2567 1.0717 0.8587 0.021 Uiso calc R 1 . . C C14 0.2502(2) 0.8995(5) 0.78572(9) 0.0205(5) Uani d . 1 . . H H14 0.1795 1.0103 0.7691 0.025 Uiso calc R 1 . . C C15 0.3108(2) 0.6995(5) 0.75814(8) 0.0205(5) Uani d . 1 . . C C16 0.4140(2) 0.5319(5) 0.78033(9) 0.0212(5) Uani d . 1 . . H H16 0.4532 0.3954 0.76 0.025 Uiso calc R 1 . . C C17 0.4582(2) 0.5703(4) 0.83324(9) 0.0179(4) Uani d . 1 . . H H17 0.5295 0.4594 0.8495 0.021 Uiso calc R 1 . . F F18 0.2657(2) 0.6602(2) 0.70623(5) 0.0294(4) Uani d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0123(2) 0.0131(2) 0.0122(2) -0.00034(18) -0.0003(2) 0.0007(2) O2 0.0208(5) 0.0137(7) 0.0172(9) -0.0020(5) -0.0033(5) 0.0010(7) O3 0.0142(5) 0.0228(8) 0.0173(8) 0.0022(5) -0.0014(5) 0.0021(8) C4 0.0152(9) 0.0164(11) 0.0105(9) -0.0037(8) 0.0005(7) 0.0015(9) C5 0.0203(10) 0.0145(11) 0.0167(11) 0.0020(9) 0.0001(9) 0.0030(10) C6 0.0302(11) 0.0181(11) 0.0145(10) -0.0010(10) 0.0045(9) -0.0005(10) C7 0.0275(11) 0.0202(13) 0.0106(10) -0.0083(10) -0.0002(8) 0.0021(10) C8 0.0206(10) 0.0228(11) 0.0145(10) 0.0004(9) -0.0009(9) 0.0048(10) C9 0.0164(9) 0.0160(11) 0.0156(11) 0.0007(9) 0.0018(8) 0.0020(9) F10 0.0386(8) 0.0338(9) 0.0105(5) -0.0078(7) -0.0045(5) -0.0021(5) C11 0.0133(9) 0.0144(11) 0.0131(10) -0.0030(8) 0.0010(7) 0.0002(9) C12 0.0136(8) 0.0154(11) 0.0106(9) -0.0035(8) -0.0007(8) 0.0015(9) C13 0.0191(10) 0.0169(11) 0.0162(10) -0.0012(9) 0.0022(8) -0.0013(11) C14 0.0201(10) 0.0236(11) 0.0179(11) 0.0017(10) -0.0022(8) 0.0040(11) C15 0.0225(11) 0.0299(14) 0.0090(10) -0.0059(11) -0.0002(8) 0.0000(10) C16 0.0240(11) 0.0223(13) 0.0172(11) 0.0028(10) 0.0017(9) -0.0055(10) C17 0.0195(10) 0.0176(11) 0.0165(10) 0.0023(9) 0.0001(9) -0.0008(11) F18 0.0367(8) 0.0414(9) 0.0102(7) 0.0015(7) -0.0059(5) -0.0020(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O3 . 1.4433(14) ? S1 O2 . 1.4453(15) ? S1 C4 . 1.774(2) ? S1 C11 . 1.786(2) ? C4 C5 . 1.380(3) ? C4 C9 . 1.386(3) ? C5 C6 . 1.397(3) ? C5 H5 . 0.95 ? C6 C7 . 1.374(3) ? C6 H6 . 0.95 ? C7 F10 . 1.357(2) ? C7 C8 . 1.373(3) ? C8 C9 . 1.392(3) ? C8 H8 . 0.95 ? C9 H9 . 0.95 ? C11 C12 . 1.505(3) ? C11 H11A . 0.99 ? C11 H11B . 0.99 ? C12 C17 . 1.392(3) ? C12 C13 . 1.395(3) ? C13 C14 . 1.390(3) ? C13 H13 . 0.95 ? C14 C15 . 1.374(3) ? C14 H14 . 0.95 ? C15 F18 . 1.366(3) ? C15 C16 . 1.386(3) ? C16 C17 . 1.387(3) ? C16 H16 . 0.95 ? C17 H17 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 S1 O2 . . 117.59(9) ? O3 S1 C4 . . 107.74(10) ? O2 S1 C4 . . 108.51(10) ? O3 S1 C11 . . 108.74(9) ? O2 S1 C11 . . 109.94(10) ? C4 S1 C11 . . 103.37(10) ? C5 C4 C9 . . 122.2(2) ? C5 C4 S1 . . 118.87(17) ? C9 C4 S1 . . 118.90(17) ? C4 C5 C6 . . 118.5(2) ? C4 C5 H5 . . 120.7 ? C6 C5 H5 . . 120.7 ? C7 C6 C5 . . 118.4(2) ? C7 C6 H6 . . 120.8 ? C5 C6 H6 . . 120.8 ? F10 C7 C8 . . 118.3(2) ? F10 C7 C6 . . 118.0(2) ? C8 C7 C6 . . 123.7(2) ? C7 C8 C9 . . 117.8(2) ? C7 C8 H8 . . 121.1 ? C9 C8 H8 . . 121.1 ? C4 C9 C8 . . 119.3(2) ? C4 C9 H9 . . 120.4 ? C8 C9 H9 . . 120.4 ? C12 C11 S1 . . 109.62(14) ? C12 C11 H11A . . 109.7 ? S1 C11 H11A . . 109.7 ? C12 C11 H11B . . 109.7 ? S1 C11 H11B . . 109.7 ? H11A C11 H11B . . 108.2 ? C17 C12 C13 . . 119.5(2) ? C17 C12 C11 . . 120.4(2) ? C13 C12 C11 . . 120.1(2) ? C14 C13 C12 . . 120.7(2) ? C14 C13 H13 . . 119.7 ? C12 C13 H13 . . 119.7 ? C15 C14 C13 . . 117.8(2) ? C15 C14 H14 . . 121.1 ? C13 C14 H14 . . 121.1 ? F18 C15 C14 . . 118.7(2) ? F18 C15 C16 . . 117.7(2) ? C14 C15 C16 . . 123.6(2) ? C15 C16 C17 . . 117.7(2) ? C15 C16 H16 . . 121.2 ? C17 C16 H16 . . 121.2 ? C16 C17 C12 . . 120.8(2) ? C16 C17 H17 . . 119.6 ? C12 C17 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O3 S1 C4 C5 . . . . -23.6(2) ? O2 S1 C4 C5 . . . . -151.95(17) ? C11 S1 C4 C5 . . . . 91.4(2) ? O3 S1 C4 C9 . . . . 156.65(16) ? O2 S1 C4 C9 . . . . 28.4(2) ? C11 S1 C4 C9 . . . . -88.35(18) ? C9 C4 C5 C6 . . . . 0.1(3) ? S1 C4 C5 C6 . . . . -179.60(17) ? C4 C5 C6 C7 . . . . 0.9(3) ? C5 C6 C7 F10 . . . . 178.3(2) ? C5 C6 C7 C8 . . . . -1.3(4) ? F10 C7 C8 C9 . . . . -179.1(2) ? C6 C7 C8 C9 . . . . 0.6(4) ? C5 C4 C9 C8 . . . . -0.8(3) ? S1 C4 C9 C8 . . . . 178.86(17) ? C7 C8 C9 C4 . . . . 0.5(3) ? O3 S1 C11 C12 . . . . -64.85(16) ? O2 S1 C11 C12 . . . . 65.18(16) ? C4 S1 C11 C12 . . . . -179.14(15) ? S1 C11 C12 C17 . . . . -93.1(2) ? S1 C11 C12 C13 . . . . 85.9(2) ? C17 C12 C13 C14 . . . . 0.8(3) ? C11 C12 C13 C14 . . . . -178.3(2) ? C12 C13 C14 C15 . . . . -0.5(3) ? C13 C14 C15 F18 . . . . 179.2(2) ? C13 C14 C15 C16 . . . . 0.2(4) ? F18 C15 C16 C17 . . . . -179.2(2) ? C14 C15 C16 C17 . . . . -0.2(3) ? C15 C16 C17 C12 . . . . 0.5(3) ? C13 C12 C17 C16 . . . . -0.8(3) ? C11 C12 C17 C16 . . . . 178.2(2) ? #===END============================================================== data_compound_06 _database_code_depnum_ccdc_archive 'CCDC 759279' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 O4 S' _chemical_formula_sum 'C15 H16 O4 S' _chemical_formula_weight 292.34 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' 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 Pc _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 15.345(14) _cell_length_b 5.395(2) _cell_length_c 8.604(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.57(3) _cell_angle_gamma 90.00 _cell_volume 686.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4.66 _cell_measurement_theta_max 16.91 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius MACH3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 2756 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.45 _reflns_number_total 2556 _reflns_number_gt 1966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'PLATON (Spek, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.1514P)^2^+0.0536P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unk _refine_ls_abs_structure_Flack 0.3(2) _refine_ls_number_reflns 2556 _refine_ls_number_parameters 183 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1135 _refine_ls_R_factor_gt 0.0809 _refine_ls_wR_factor_ref 0.2263 _refine_ls_wR_factor_gt 0.1918 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.065 _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 C1 C 0.2246(5) -0.0118(18) 0.5067(12) 0.041(2) Uani 1 1 d . . . H1A H 0.2109 -0.0026 0.6114 0.062 Uiso 1 1 calc R . . H1B H 0.2594 -0.1627 0.5021 0.062 Uiso 1 1 calc R . . H1C H 0.1680 -0.0156 0.4203 0.062 Uiso 1 1 calc R . . O2 O 0.2762(3) 0.1995(10) 0.4869(6) 0.0340(13) Uani 1 1 d . . . C3 C 0.3626(4) 0.2136(13) 0.5870(8) 0.0230(15) Uani 1 1 d . . . C4 C 0.3994(5) 0.0498(14) 0.7086(8) 0.0300(17) Uani 1 1 d . . . H4 H 0.3643 -0.0846 0.7300 0.036 Uiso 1 1 calc R . . C5 C 0.4890(5) 0.0813(14) 0.8015(8) 0.0280(17) Uani 1 1 d . . . H5 H 0.5145 -0.0321 0.8859 0.034 Uiso 1 1 calc R . . C6 C 0.5399(5) 0.2750(13) 0.7712(8) 0.0222(15) Uani 1 1 d . . . C7 C 0.5016(6) 0.4418(15) 0.6492(10) 0.0311(19) Uani 1 1 d . . . H7 H 0.5364 0.5776 0.6290 0.037 Uiso 1 1 calc R . . C8 C 0.4141(5) 0.4130(15) 0.5574(9) 0.0306(18) Uani 1 1 d . . . H8 H 0.3886 0.5281 0.4740 0.037 Uiso 1 1 calc R . . C9 C 0.6368(5) 0.3066(14) 0.8690(8) 0.0268(17) Uani 1 1 d . . . H9A H 0.6452 0.2326 0.9774 0.032 Uiso 1 1 calc R . . H9B H 0.6520 0.4850 0.8824 0.032 Uiso 1 1 calc R . . S10 S 0.70940(12) 0.1553(3) 0.76561(18) 0.0211(4) Uani 1 1 d . . . O11 O 0.7008(3) 0.2840(9) 0.6143(6) 0.0300(12) Uani 1 1 d . . . O12 O 0.6937(4) -0.1064(9) 0.7604(7) 0.0261(12) Uani 1 1 d . . . C13 C 0.8199(4) 0.2101(13) 0.8890(8) 0.0211(15) Uani 1 1 d . . . C14 C 0.8570(5) 0.0418(13) 1.0122(8) 0.0238(15) Uani 1 1 d . . . H14 H 0.8236 -0.0997 1.0281 0.029 Uiso 1 1 calc R . . C15 C 0.9432(5) 0.0835(14) 1.1110(9) 0.0287(17) Uani 1 1 d . . . H15 H 0.9684 -0.0265 1.1975 0.034 Uiso 1 1 calc R . . C16 C 0.9927(5) 0.2870(13) 1.0832(8) 0.0241(16) Uani 1 1 d . . . C17 C 0.9556(6) 0.4528(15) 0.9585(10) 0.0305(18) Uani 1 1 d . . . H17 H 0.9899 0.5900 0.9386 0.037 Uiso 1 1 calc R . . C18 C 0.8692(5) 0.4151(13) 0.8653(8) 0.0253(16) Uani 1 1 d . . . H18 H 0.8426 0.5312 0.7832 0.030 Uiso 1 1 calc R . . O19 O 1.0774(3) 0.3093(11) 1.1853(6) 0.0354(13) Uani 1 1 d . . . C20 C 1.1313(5) 0.5154(16) 1.1591(10) 0.040(2) Uani 1 1 d . . . H20A H 1.1012 0.6709 1.1728 0.060 Uiso 1 1 calc R . . H20B H 1.1385 0.5070 1.0495 0.060 Uiso 1 1 calc R . . H20C H 1.1909 0.5085 1.2373 0.060 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 C1 0.032(5) 0.047(5) 0.042(4) -0.008(4) 0.004(4) -0.002(4) O2 0.021(2) 0.046(4) 0.033(3) 0.001(3) 0.002(2) -0.002(2) C3 0.019(3) 0.035(4) 0.013(3) -0.003(3) 0.001(2) 0.002(3) C4 0.033(4) 0.034(4) 0.025(4) -0.002(3) 0.010(3) -0.009(3) C5 0.029(4) 0.036(4) 0.016(3) 0.003(3) 0.001(3) -0.001(3) C6 0.027(4) 0.026(4) 0.015(3) -0.001(3) 0.009(3) 0.001(3) C7 0.031(4) 0.037(5) 0.030(4) -0.002(3) 0.017(4) -0.004(4) C8 0.035(4) 0.030(4) 0.028(4) 0.009(3) 0.009(3) 0.002(3) C9 0.035(4) 0.032(4) 0.019(3) -0.003(3) 0.017(3) -0.001(3) S10 0.0233(7) 0.0284(8) 0.0114(6) 0.0006(9) 0.0041(5) 0.0021(9) O11 0.035(3) 0.046(3) 0.010(2) 0.006(2) 0.0081(19) 0.004(2) O12 0.033(3) 0.036(3) 0.0074(17) -0.001(2) 0.002(2) -0.001(2) C13 0.018(3) 0.031(4) 0.014(3) -0.002(3) 0.003(2) 0.004(3) C14 0.024(4) 0.026(4) 0.022(3) 0.006(3) 0.007(3) -0.003(3) C15 0.021(4) 0.040(5) 0.023(3) 0.003(3) 0.002(3) 0.004(3) C16 0.024(3) 0.030(4) 0.019(3) -0.004(3) 0.006(3) 0.001(3) C17 0.033(4) 0.028(4) 0.031(4) 0.000(3) 0.010(4) 0.002(3) C18 0.031(4) 0.019(3) 0.025(4) 0.007(3) 0.007(3) 0.002(3) O19 0.022(2) 0.049(4) 0.033(3) 0.000(3) 0.004(2) -0.004(2) C20 0.026(4) 0.045(5) 0.044(5) -0.001(4) 0.000(4) -0.007(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 C1 O2 1.424(11) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C3 1.376(8) . ? C3 C4 1.370(10) . ? C3 C8 1.398(10) . ? C4 C5 1.403(10) . ? C4 H4 0.9500 . ? C5 C6 1.372(10) . ? C5 H5 0.9500 . ? C6 C7 1.387(10) . ? C6 C9 1.508(10) . ? C7 C8 1.371(11) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 S10 1.798(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? S10 O12 1.431(5) . ? S10 O11 1.450(5) . ? S10 C13 1.767(7) . ? C13 C18 1.386(10) . ? C13 C14 1.396(9) . ? C14 C15 1.385(10) . ? C14 H14 0.9500 . ? C15 C16 1.392(11) . ? C15 H15 0.9500 . ? C16 O19 1.364(8) . ? C16 C17 1.395(10) . ? C17 C18 1.368(11) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? O19 C20 1.439(10) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O2 C1 116.3(6) . . ? C4 C3 O2 124.9(6) . . ? C4 C3 C8 119.9(6) . . ? O2 C3 C8 115.1(6) . . ? C3 C4 C5 119.8(7) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.4(7) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 119.4(7) . . ? C5 C6 C9 120.4(6) . . ? C7 C6 C9 120.2(7) . . ? C8 C7 C6 120.9(7) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C3 119.7(7) . . ? C7 C8 H8 120.1 . . ? C3 C8 H8 120.1 . . ? C6 C9 S10 108.8(5) . . ? C6 C9 H9A 109.9 . . ? S10 C9 H9A 109.9 . . ? C6 C9 H9B 109.9 . . ? S10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? O12 S10 O11 118.1(3) . . ? O12 S10 C13 108.1(3) . . ? O11 S10 C13 107.5(3) . . ? O12 S10 C9 110.0(3) . . ? O11 S10 C9 107.9(3) . . ? C13 S10 C9 104.4(3) . . ? C18 C13 C14 120.2(6) . . ? C18 C13 S10 121.3(5) . . ? C14 C13 S10 118.6(5) . . ? C15 C14 C13 119.2(7) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 119.9(7) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? O19 C16 C15 115.4(6) . . ? O19 C16 C17 124.1(7) . . ? C15 C16 C17 120.5(6) . . ? C18 C17 C16 119.2(7) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C13 120.9(7) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? C16 O19 C20 117.1(6) . . ? O19 C20 H20A 109.5 . . ? O19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C1 O2 C3 C4 -4.3(10) . . . . ? C1 O2 C3 C8 175.5(7) . . . . ? O2 C3 C4 C5 179.0(6) . . . . ? C8 C3 C4 C5 -0.8(11) . . . . ? C3 C4 C5 C6 0.0(11) . . . . ? C4 C5 C6 C7 0.9(11) . . . . ? C4 C5 C6 C9 -178.9(6) . . . . ? C5 C6 C7 C8 -1.0(11) . . . . ? C9 C6 C7 C8 178.9(7) . . . . ? C6 C7 C8 C3 0.1(12) . . . . ? C4 C3 C8 C7 0.8(11) . . . . ? O2 C3 C8 C7 -179.1(7) . . . . ? C5 C6 C9 S10 93.3(7) . . . . ? C7 C6 C9 S10 -86.6(7) . . . . ? C6 C9 S10 O12 -65.4(5) . . . . ? C6 C9 S10 O11 64.7(5) . . . . ? C6 C9 S10 C13 178.9(5) . . . . ? O12 S10 C13 C18 151.8(6) . . . . ? O11 S10 C13 C18 23.3(6) . . . . ? C9 S10 C13 C18 -91.2(6) . . . . ? O12 S10 C13 C14 -28.3(6) . . . . ? O11 S10 C13 C14 -156.8(5) . . . . ? C9 S10 C13 C14 88.7(6) . . . . ? C18 C13 C14 C15 0.5(10) . . . . ? S10 C13 C14 C15 -179.3(5) . . . . ? C13 C14 C15 C16 -2.1(11) . . . . ? C14 C15 C16 O19 -178.9(6) . . . . ? C14 C15 C16 C17 1.4(11) . . . . ? O19 C16 C17 C18 -178.7(7) . . . . ? C15 C16 C17 C18 1.0(11) . . . . ? C16 C17 C18 C13 -2.6(12) . . . . ? C14 C13 C18 C17 1.9(11) . . . . ? S10 C13 C18 C17 -178.2(6) . . . . ? C15 C16 O19 C20 179.1(7) . . . . ? C17 C16 O19 C20 -1.2(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.45 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.775 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.115 #===END============================================================== data_compound_07 _database_code_depnum_ccdc_archive 'CCDC 759280' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 F N O4 S' _chemical_formula_sum 'C13 H10 F N O4 S' _chemical_formula_weight 295.28 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' F F 0.0171 0.0103 '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 Pc _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 13.0726(6) _cell_length_b 5.2890(2) _cell_length_c 8.9303(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.231(3) _cell_angle_gamma 90.00 _cell_volume 617.44(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1547 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The 1 0 0, 2 0 0 and -2 0 0 reflections have been omitted due to the beamstop. absolute configuration test conclusive. correct enantiomer R1=0.0263, wR2=0.0675 incorrect enantiomer R1=0.0281, wR2=0.0728 refining in SHELXL-97 using TWIN,BASF refined to 0.00001 for the correct enantiomer. ; _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 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8984 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2674 _reflns_number_gt 2607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0418P)^2^+0.0945P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(5) _chemical_absolute_configuration ad _refine_ls_number_reflns 2674 _refine_ls_number_parameters 181 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0272 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0667 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 F1 F 0.54777(7) 0.6553(2) 0.60847(12) 0.0278(2) Uani 1 1 d . . . C2 C 0.45089(12) 0.6994(3) 0.65292(18) 0.0204(3) Uani 1 1 d . . . C3 C 0.40840(13) 0.5366(3) 0.7562(2) 0.0230(4) Uani 1 1 d . . . H3 H 0.4462 0.3970 0.7941 0.028 Uiso 1 1 calc R . . C4 C 0.30911(13) 0.5819(3) 0.80337(19) 0.0202(3) Uani 1 1 d . . . H4 H 0.2776 0.4729 0.8740 0.024 Uiso 1 1 calc R . . C5 C 0.25624(12) 0.7888(3) 0.74599(16) 0.0147(3) Uani 1 1 d . . . C6 C 0.30078(12) 0.9520(3) 0.64187(17) 0.0174(3) Uani 1 1 d . . . H6 H 0.2636 1.0927 0.6042 0.021 Uiso 1 1 calc R . . C7 C 0.39998(12) 0.9060(3) 0.59407(19) 0.0212(3) Uani 1 1 d . . . H7 H 0.4319 1.0134 0.5230 0.025 Uiso 1 1 calc R . . S8 S 0.13053(3) 0.85014(6) 0.80569(4) 0.01297(9) Uani 1 1 d . . . O9 O 0.11479(9) 0.7265(2) 0.94719(13) 0.0192(2) Uani 1 1 d . . . O10 O 0.11210(8) 1.11952(19) 0.79927(14) 0.0180(3) Uani 1 1 d . . . C11 C 0.05291(12) 0.6952(3) 0.66750(17) 0.0155(3) Uani 1 1 d . . . H11A H 0.0682 0.7630 0.5667 0.019 Uiso 1 1 calc R . . H11B H 0.0672 0.5113 0.6674 0.019 Uiso 1 1 calc R . . C12 C -0.05764(11) 0.7423(3) 0.70572(16) 0.0143(3) Uani 1 1 d . . . C13 C -0.10818(12) 0.5829(3) 0.80639(17) 0.0173(3) Uani 1 1 d . . . H13 H -0.0742 0.4379 0.8449 0.021 Uiso 1 1 calc R . . C14 C -0.20768(12) 0.6355(3) 0.85021(18) 0.0185(3) Uani 1 1 d . . . H14 H -0.2427 0.5275 0.9178 0.022 Uiso 1 1 calc R . . C15 C -0.25459(11) 0.8497(3) 0.79292(18) 0.0169(3) Uani 1 1 d . . . C16 C -0.20800(12) 1.0070(3) 0.69020(19) 0.0193(3) Uani 1 1 d . . . H16 H -0.2431 1.1493 0.6504 0.023 Uiso 1 1 calc R . . C17 C -0.10853(12) 0.9521(3) 0.64636(17) 0.0179(3) Uani 1 1 d . . . H17 H -0.0750 1.0576 0.5758 0.022 Uiso 1 1 calc R . . N18 N -0.35792(10) 0.9170(3) 0.84597(15) 0.0210(3) Uani 1 1 d . . . O19 O -0.39841(9) 0.7768(3) 0.93685(15) 0.0296(3) Uani 1 1 d . . . O20 O -0.39668(9) 1.1124(3) 0.79786(16) 0.0304(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 F1 0.0144(5) 0.0366(6) 0.0324(6) -0.0083(4) 0.0052(4) 0.0045(4) C2 0.0123(7) 0.0264(8) 0.0223(8) -0.0070(7) 0.0004(6) 0.0008(6) C3 0.0173(8) 0.0215(9) 0.0303(9) 0.0001(7) -0.0027(7) 0.0050(6) C4 0.0197(8) 0.0179(8) 0.0229(8) 0.0018(6) -0.0015(6) 0.0007(6) C5 0.0119(6) 0.0171(7) 0.0150(7) -0.0025(6) -0.0007(6) -0.0003(6) C6 0.0164(7) 0.0179(7) 0.0179(7) 0.0018(6) -0.0009(6) -0.0008(6) C7 0.0168(8) 0.0258(8) 0.0211(8) -0.0005(7) 0.0035(6) -0.0041(6) S8 0.01300(16) 0.01369(16) 0.01224(16) -0.00016(14) 0.00100(11) -0.00013(14) O9 0.0200(5) 0.0236(6) 0.0140(5) 0.0041(5) 0.0014(4) -0.0013(5) O10 0.0195(7) 0.0125(5) 0.0220(5) -0.0013(5) 0.0036(5) 0.0008(4) C11 0.0142(7) 0.0178(7) 0.0146(7) -0.0023(6) 0.0004(5) -0.0010(6) C12 0.0137(7) 0.0156(7) 0.0135(7) -0.0030(6) -0.0004(5) -0.0006(6) C13 0.0173(7) 0.0155(7) 0.0190(8) -0.0013(6) -0.0008(6) 0.0008(6) C14 0.0168(8) 0.0209(8) 0.0177(8) -0.0006(6) 0.0030(6) -0.0043(6) C15 0.0118(7) 0.0216(8) 0.0172(7) -0.0050(6) -0.0003(6) 0.0002(5) C16 0.0185(8) 0.0214(9) 0.0181(7) 0.0013(6) -0.0022(6) 0.0041(6) C17 0.0181(8) 0.0198(8) 0.0159(7) 0.0021(6) 0.0002(6) -0.0003(6) N18 0.0142(7) 0.0285(7) 0.0204(8) -0.0056(6) -0.0004(6) 0.0021(6) O19 0.0191(6) 0.0397(7) 0.0301(7) 0.0019(6) 0.0081(5) -0.0007(5) O20 0.0212(7) 0.0344(8) 0.0357(7) -0.0017(6) 0.0019(6) 0.0100(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 F1 C2 1.3489(18) . ? C2 C3 1.380(2) . ? C2 C7 1.382(2) . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 C6 1.397(2) . ? C5 S8 1.7600(16) . ? C6 C7 1.388(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? S8 O9 1.4384(12) . ? S8 O10 1.4461(11) . ? S8 C11 1.7928(15) . ? C11 C12 1.507(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.397(2) . ? C12 C13 1.400(2) . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 C15 1.385(2) . ? C14 H14 0.9500 . ? C15 C16 1.382(2) . ? C15 N18 1.477(2) . ? C16 C17 1.390(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N18 O19 1.221(2) . ? N18 O20 1.228(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 F1 C2 C3 118.01(15) . . ? F1 C2 C7 118.42(15) . . ? C3 C2 C7 123.56(15) . . ? C2 C3 C4 118.34(15) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C3 C4 C5 119.23(16) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 121.55(14) . . ? C4 C5 S8 119.78(12) . . ? C6 C5 S8 118.67(11) . . ? C7 C6 C5 119.25(14) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C2 C7 C6 118.07(15) . . ? C2 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? O9 S8 O10 117.28(7) . . ? O9 S8 C5 108.62(7) . . ? O10 S8 C5 108.98(7) . . ? O9 S8 C11 108.32(7) . . ? O10 S8 C11 109.23(7) . . ? C5 S8 C11 103.52(7) . . ? C12 C11 S8 108.00(10) . . ? C12 C11 H11A 110.1 . . ? S8 C11 H11A 110.1 . . ? C12 C11 H11B 110.1 . . ? S8 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? C17 C12 C13 119.79(14) . . ? C17 C12 C11 120.07(13) . . ? C13 C12 C11 120.08(14) . . ? C14 C13 C12 120.35(15) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 118.29(15) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C16 C15 C14 122.82(15) . . ? C16 C15 N18 118.30(14) . . ? C14 C15 N18 118.87(14) . . ? C15 C16 C17 118.47(14) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C16 C17 C12 120.22(14) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? O19 N18 O20 124.34(14) . . ? O19 N18 C15 117.79(14) . . ? O20 N18 C15 117.86(14) . . ? 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 F1 C2 C3 C4 179.48(14) . . . . ? C7 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ? C3 C4 C5 S8 -179.55(12) . . . . ? C4 C5 C6 C7 0.3(2) . . . . ? S8 C5 C6 C7 179.87(12) . . . . ? F1 C2 C7 C6 -179.17(14) . . . . ? C3 C2 C7 C6 0.1(3) . . . . ? C5 C6 C7 C2 -0.3(2) . . . . ? C4 C5 S8 O9 21.11(14) . . . . ? C6 C5 S8 O9 -158.51(12) . . . . ? C4 C5 S8 O10 149.98(12) . . . . ? C6 C5 S8 O10 -29.64(14) . . . . ? C4 C5 S8 C11 -93.86(13) . . . . ? C6 C5 S8 C11 86.53(13) . . . . ? O9 S8 C11 C12 66.39(12) . . . . ? O10 S8 C11 C12 -62.43(12) . . . . ? C5 S8 C11 C12 -178.42(10) . . . . ? S8 C11 C12 C17 90.73(14) . . . . ? S8 C11 C12 C13 -86.22(15) . . . . ? C17 C12 C13 C14 -1.5(2) . . . . ? C11 C12 C13 C14 175.42(13) . . . . ? C12 C13 C14 C15 -0.6(2) . . . . ? C13 C14 C15 C16 2.5(2) . . . . ? C13 C14 C15 N18 -176.12(13) . . . . ? C14 C15 C16 C17 -2.2(2) . . . . ? N18 C15 C16 C17 176.44(13) . . . . ? C15 C16 C17 C12 0.0(2) . . . . ? C13 C12 C17 C16 1.8(2) . . . . ? C11 C12 C17 C16 -175.11(14) . . . . ? C16 C15 N18 O19 -179.95(15) . . . . ? C14 C15 N18 O19 -1.3(2) . . . . ? C16 C15 N18 O20 -1.2(2) . . . . ? C14 C15 N18 O20 177.45(15) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.174 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.046 #===END============================================================== data_compound_09 _database_code_depnum_ccdc_archive 'CCDC 759281' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O4 S' _chemical_formula_sum 'C16 H18 O4 S' _chemical_formula_weight 306.36 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' 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 C1c1 _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 17.924(4) _cell_length_b 9.756(3) _cell_length_c 8.6720(17) _cell_angle_alpha 90.00 _cell_angle_beta 92.355(8) _cell_angle_gamma 90.00 _cell_volume 1515.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1206 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 21.83 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8175 _exptl_absorpt_correction_T_max 0.9583 _exptl_absorpt_process_details 'Sadabs Version 2007/2' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7227 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 25.09 _reflns_number_total 2647 _reflns_number_gt 1898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL--97; PLATON' _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^)+(0.0262P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(7) _chemical_absolute_configuration ad _refine_ls_number_reflns 2647 _refine_ls_number_parameters 193 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.006 _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 S1 S 0.91085(4) 0.87356(9) 0.28831(7) 0.0569(2) Uani 1 1 d . . . O1 O 0.55227(12) 0.9173(2) 0.1852(3) 0.0728(6) Uani 1 1 d . . . O2 O 1.22516(11) 0.8792(2) 0.1203(2) 0.0651(6) Uani 1 1 d . . . O3 O 0.88862(11) 1.0151(2) 0.2937(3) 0.0738(7) Uani 1 1 d . . . O4 O 0.90414(12) 0.7914(3) 0.4250(2) 0.0825(7) Uani 1 1 d . . . C1 C 0.50619(18) 0.8440(4) 0.2842(5) 0.0885(12) Uani 1 1 d . . . H1A H 0.5000 0.7518 0.2471 0.133 Uiso 1 1 calc R . . H1B H 0.4583 0.8878 0.2865 0.133 Uiso 1 1 calc R . . H1C H 0.5289 0.8424 0.3864 0.133 Uiso 1 1 calc R . . C2 C 0.62591(17) 0.8798(3) 0.1793(3) 0.0504(7) Uani 1 1 d . . . C3 C 0.65865(16) 0.7756(3) 0.2625(3) 0.0533(8) Uani 1 1 d . . . H3 H 0.6307 0.7248 0.3302 0.064 Uiso 1 1 calc R . . C4 C 0.73369(18) 0.7454(3) 0.2461(3) 0.0570(8) Uani 1 1 d . . . H4 H 0.7553 0.6733 0.3021 0.068 Uiso 1 1 calc R . . C5 C 0.77716(15) 0.8210(3) 0.1473(3) 0.0441(7) Uani 1 1 d . . . C6 C 0.85892(15) 0.7918(3) 0.1308(3) 0.0504(8) Uani 1 1 d . . . H6 H 0.8740 0.8345 0.0346 0.061 Uiso 1 1 calc R . . C7 C 1.00466(14) 0.8679(3) 0.2358(3) 0.0452(7) Uani 1 1 d . . . C8 C 1.05365(17) 0.7752(3) 0.3041(3) 0.0535(8) Uani 1 1 d . . . H8 H 1.0365 0.7118 0.3745 0.064 Uiso 1 1 calc R . . C9 C 1.12815(16) 0.7759(3) 0.2684(3) 0.0524(8) Uani 1 1 d . . . H9 H 1.1611 0.7133 0.3149 0.063 Uiso 1 1 calc R . . C10 C 1.15340(15) 0.8699(3) 0.1635(3) 0.0453(7) Uani 1 1 d . . . C11 C 1.28024(18) 0.7906(4) 0.1925(4) 0.0746(11) Uani 1 1 d . . . H11A H 1.2823 0.8061 0.3019 0.112 Uiso 1 1 calc R . . H11B H 1.3282 0.8096 0.1519 0.112 Uiso 1 1 calc R . . H11C H 1.2670 0.6968 0.1719 0.112 Uiso 1 1 calc R . . C12 C 0.66857(17) 0.9566(3) 0.0812(3) 0.0561(8) Uani 1 1 d . . . H12 H 0.6466 1.0285 0.0253 0.067 Uiso 1 1 calc R . . C13 C 0.74318(16) 0.9275(3) 0.0657(3) 0.0527(8) Uani 1 1 d . . . H13 H 0.7710 0.9802 -0.0003 0.063 Uiso 1 1 calc R . . C14 C 0.87986(19) 0.6399(3) 0.1244(4) 0.0746(10) Uani 1 1 d . . . H14A H 0.8697 0.5972 0.2210 0.112 Uiso 1 1 calc R . . H14B H 0.9320 0.6313 0.1053 0.112 Uiso 1 1 calc R . . H14C H 0.8510 0.5960 0.0428 0.112 Uiso 1 1 calc R . . C15 C 1.02965(17) 0.9615(3) 0.1296(3) 0.0544(8) Uani 1 1 d . . . H15 H 0.9967 1.0241 0.0829 0.065 Uiso 1 1 calc R . . C16 C 1.10374(17) 0.9608(3) 0.0938(3) 0.0562(8) Uani 1 1 d . . . H16 H 1.1206 1.0227 0.0214 0.067 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 0.0399(4) 0.0825(6) 0.0488(4) -0.0094(5) 0.0059(3) 0.0001(4) O1 0.0414(14) 0.0853(17) 0.0923(16) 0.0033(14) 0.0098(12) 0.0089(12) O2 0.0416(12) 0.0812(16) 0.0733(14) 0.0031(12) 0.0108(10) 0.0018(11) O3 0.0507(14) 0.0780(16) 0.0930(16) -0.0352(14) 0.0062(12) 0.0100(12) O4 0.0536(14) 0.143(2) 0.0510(14) 0.0128(14) 0.0075(11) -0.0081(14) C1 0.039(2) 0.116(4) 0.112(3) -0.001(3) 0.019(2) -0.003(2) C2 0.0422(18) 0.0533(19) 0.0555(19) -0.0127(15) 0.0003(14) -0.0027(16) C3 0.0434(19) 0.058(2) 0.060(2) 0.0057(16) 0.0100(15) -0.0056(15) C4 0.0475(18) 0.062(2) 0.061(2) 0.0120(15) 0.0009(15) 0.0019(16) C5 0.0402(17) 0.0469(18) 0.0454(17) -0.0051(14) 0.0024(13) -0.0022(13) C6 0.0434(17) 0.064(2) 0.0440(17) -0.0060(14) 0.0033(13) 0.0016(14) C7 0.0324(15) 0.061(2) 0.0420(17) -0.0044(15) 0.0000(13) 0.0015(15) C8 0.0507(19) 0.058(2) 0.0522(19) 0.0031(15) 0.0077(15) -0.0021(16) C9 0.0404(18) 0.060(2) 0.057(2) 0.0038(15) 0.0026(15) 0.0052(15) C10 0.0359(16) 0.0533(18) 0.0470(16) -0.0082(14) 0.0053(13) -0.0030(15) C11 0.043(2) 0.085(3) 0.095(3) -0.002(2) 0.0014(18) 0.0150(18) C12 0.055(2) 0.054(2) 0.060(2) 0.0080(15) -0.0023(16) 0.0070(15) C13 0.051(2) 0.0561(19) 0.0517(18) 0.0027(15) 0.0079(15) -0.0035(15) C14 0.061(2) 0.074(2) 0.089(3) -0.009(2) 0.0125(17) 0.0066(19) C15 0.0459(19) 0.061(2) 0.056(2) 0.0076(15) 0.0017(15) 0.0096(15) C16 0.053(2) 0.058(2) 0.058(2) 0.0104(15) 0.0060(15) -0.0028(16) _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 O3 1.438(2) . ? S1 O4 1.440(2) . ? S1 C7 1.761(3) . ? S1 C6 1.807(3) . ? O1 C2 1.372(4) . ? O1 C1 1.410(4) . ? O2 C10 1.358(3) . ? O2 C11 1.437(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.366(4) . ? C2 C12 1.387(4) . ? C3 C4 1.390(4) . ? C3 H3 0.9300 . ? C4 C5 1.393(4) . ? C4 H4 0.9300 . ? C5 C13 1.384(4) . ? C5 C6 1.505(4) . ? C6 C14 1.530(4) . ? C6 H6 0.9800 . ? C7 C8 1.378(4) . ? C7 C15 1.385(4) . ? C8 C9 1.383(4) . ? C8 H8 0.9300 . ? C9 C10 1.381(4) . ? C9 H9 0.9300 . ? C10 C16 1.379(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.379(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.376(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O4 118.33(15) . . ? O3 S1 C7 107.89(14) . . ? O4 S1 C7 107.97(13) . . ? O3 S1 C6 108.27(14) . . ? O4 S1 C6 108.60(15) . . ? C7 S1 C6 104.99(13) . . ? C2 O1 C1 118.4(3) . . ? C10 O2 C11 118.8(2) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 O1 124.8(3) . . ? C3 C2 C12 119.4(3) . . ? O1 C2 C12 115.8(3) . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 121.3(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C13 C5 C4 117.8(3) . . ? C13 C5 C6 120.2(2) . . ? C4 C5 C6 122.0(3) . . ? C5 C6 C14 115.3(2) . . ? C5 C6 S1 108.55(19) . . ? C14 C6 S1 109.6(2) . . ? C5 C6 H6 107.7 . . ? C14 C6 H6 107.7 . . ? S1 C6 H6 107.7 . . ? C8 C7 C15 120.1(3) . . ? C8 C7 S1 120.5(2) . . ? C15 C7 S1 119.3(2) . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 119.8(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? O2 C10 C16 115.9(3) . . ? O2 C10 C9 124.5(3) . . ? C16 C10 C9 119.5(3) . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C2 120.7(3) . . ? C13 C12 H12 119.7 . . ? C2 C12 H12 119.7 . . ? C12 C13 C5 120.9(3) . . ? C12 C13 H13 119.6 . . ? C5 C13 H13 119.6 . . ? C6 C14 H14A 109.5 . . ? C6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C7 119.2(3) . . ? C16 C15 H15 120.4 . . ? C7 C15 H15 120.4 . . ? C15 C16 C10 121.0(3) . . ? C15 C16 H16 119.5 . . ? C10 C16 H16 119.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.111 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.033 #===END============================================================== data_compound_10 _database_code_depnum_ccdc_archive 'CCDC 759282' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C14 H12 F2 O2 S' _chemical_formula_sum 'C14 H12 F2 O2 S' _chemical_formula_iupac ? _chemical_formula_weight 282.30 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 c 1' _symmetry_space_group_name_Hall ' C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 16.3313(11) _cell_length_b 19.8342(14) _cell_length_c 8.2586(5) _cell_angle_alpha 90 _cell_angle_beta 109.308(2) _cell_angle_gamma 90 _cell_volume 2524.6(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9970 _cell_measurement_theta_min 3.3245 _cell_measurement_theta_max 27.9088 _cell_measurement_temperature 100.(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs Version 2008/1' _exptl_absorpt_correction_T_min 0.6277 _exptl_absorpt_correction_T_max 0.7456 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX DUO' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 21292 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.98 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _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. ; _reflns_number_total 6027 _reflns_number_gt 5865 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.0670 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_number_reflns 6027 _refine_ls_number_parameters 345 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.9919P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.258 _refine_diff_density_min -0.200 _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 0.02(3) _chemical_absolute_configuration ad 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _computing_data_collection 'Bruker Instrument Service v2009, 3, 0, 0' _computing_cell_refinement 'SAINT V7.60A (Bruker AXS, 2008)' _computing_data_reduction 'SAINT V7.60A (Bruker AXS, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL--97; PLATON' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.54344(2) 0.80986(16) 0.15550(4) 0.01662(6) Uani d . 1 . . O O2 0.61443(6) 0.79991(5) 0.09046(13) 0.0224(2) Uani d . 1 . . O O3 0.47435(6) 0.85567(5) 0.06470(12) 0.0223(2) Uani d . 1 . . C C4 0.58633(9) 0.83840(6) 0.37574(18) 0.0173(2) Uani d . 1 . . H H4 0.5376 0.8388 0.4239 0.021 Uiso calc R 1 . . C C5 0.65659(8) 0.78815(6) 0.48426(17) 0.0155(2) Uani d . 1 . . H H5A 0.6742 0.8009 0.6056 0.023 Uiso calc R 1 . . H H5B 0.7072 0.7895 0.4455 0.023 Uiso calc R 1 . . H H5C 0.6326 0.7424 0.4699 0.023 Uiso calc R 1 . . C C6 0.61597(9) 0.91048(6) 0.37040(17) 0.0178(2) Uani d . 1 . . C C7 0.69419(10) 0.92554(8) 0.3438(2) 0.0232(2) Uani d . 1 . . H H7 0.7311 0.89 0.3332 0.028 Uiso calc R 1 . . C C8 0.71835(11) 0.99225(8) 0.3328(2) 0.0270(2) Uani d . 1 . . H H8 0.7713 1.0027 0.3141 0.032 Uiso calc R 1 . . C C9 0.66406(11) 1.04256(8) 0.3498(2) 0.0264(2) Uani d . 1 . . C C10 0.58714(11) 1.03028(8) 0.3786(2) 0.0261(2) Uani d . 1 . . H H10 0.5517 1.0663 0.3925 0.031 Uiso calc R 1 . . C C11 0.56271(9) 0.96335(6) 0.38692(18) 0.0217(2) Uani d . 1 . . H H11 0.5092 0.9536 0.404 0.026 Uiso calc R 1 . . F F12 0.68778(8) 1.10760(5) 0.33819(13) 0.0385(2) Uani d . 1 . . C C13 0.49625(9) 0.73030(6) 0.16540(17) 0.0173(2) Uani d . 1 . . C C14 0.53585(10) 0.67255(6) 0.1315(2) 0.0229(2) Uani d . 1 . . H H14 0.5877 0.6758 0.1036 0.028 Uiso calc R 1 . . C C15 0.49885(11) 0.60987(8) 0.1390(2) 0.0270(2) Uani d . 1 . . H H15 0.5243 0.5696 0.1151 0.032 Uiso calc R 1 . . C C16 0.42445(10) 0.60789(6) 0.1819(2) 0.0242(2) Uani d . 1 . . C C17 0.38366(9) 0.66434(8) 0.2157(2) 0.0224(2) Uani d . 1 . . H H17 0.3321 0.6606 0.2442 0.027 Uiso calc R 1 . . C C18 0.42009(9) 0.72678(6) 0.20673(18) 0.0198(2) Uani d . 1 . . H H18 0.3935 0.7668 0.2285 0.024 Uiso calc R 1 . . F F19 0.38961(6) 0.54672(5) 0.19412(14) 0.0384(2) Uani d . 1 . . S S21 0.82131(2) 0.650632(16) -0.02158(4) 0.01752(6) Uani d . 1 . . O O22 0.89602(6) 0.64033(6) -0.07560(14) 0.0263(2) Uani d . 1 . . O O23 0.75056(6) 0.69135(5) -0.12609(13) 0.0254(2) Uani d . 1 . . C C24 0.85986(9) 0.68564(6) 0.19174(18) 0.0169(2) Uani d . 1 . . H H24 0.9067 0.6555 0.2648 0.02 Uiso calc R 1 . . C C25 0.78586(9) 0.68772(6) 0.27005(18) 0.0187(2) Uani d . 1 . . H H25A 0.7387 0.7163 0.199 0.028 Uiso calc R 1 . . H H25B 0.808 0.7062 0.3865 0.028 Uiso calc R 1 . . H H25C 0.764 0.642 0.2742 0.028 Uiso calc R 1 . . C C26 0.90008(9) 0.75335(6) 0.17844(17) 0.0174(2) Uani d . 1 . . C C27 0.98836(9) 0.75690(6) 0.1983(2) 0.0199(2) Uani d . 1 . . H H27 1.0224 0.717 0.2225 0.024 Uiso calc R 1 . . C C28 1.02716(10) 0.81797(8) 0.1830(2) 0.0226(2) Uani d . 1 . . H H28 1.0871 0.8205 0.196 0.027 Uiso calc R 1 . . C C29 0.97570(10) 0.87454(6) 0.1485(2) 0.0235(2) Uani d . 1 . . C C30 0.88838(10) 0.87405(6) 0.1281(2) 0.0236(2) Uani d . 1 . . H H30 0.8553 0.9145 0.1054 0.028 Uiso calc R 1 . . C C31 0.85013(10) 0.81222(6) 0.1418(2) 0.0212(2) Uani d . 1 . . H H31 0.7899 0.8102 0.1262 0.025 Uiso calc R 1 . . F F32 1.01251(6) 0.93483(5) 0.13164(14) 0.0345(2) Uani d . 1 . . C C33 0.78073(9) 0.56993(6) 0.00120(17) 0.0174(2) Uani d . 1 . . C C34 0.83849(10) 0.51620(6) 0.0562(2) 0.0213(2) Uani d . 1 . . H H34 0.8991 0.5233 0.0846 0.026 Uiso calc R 1 . . C C35 0.80668(10) 0.45222(6) 0.0693(2) 0.0244(2) Uani d . 1 . . H H35 0.8447 0.4149 0.1076 0.029 Uiso calc R 1 . . C C36 0.71779(11) 0.44464(6) 0.0245(2) 0.0228(2) Uani d . 1 . . C C37 0.65917(10) 0.49681(8) -0.0291(2) 0.0233(2) Uani d . 1 . . H H37 0.5986 0.4893 -0.0572 0.028 Uiso calc R 1 . . C C38 0.69170(10) 0.56072(6) -0.0406(2) 0.0214(2) Uani d . 1 . . H H38 0.6533 0.5979 -0.0768 0.026 Uiso calc R 1 . . F F39 0.68642(6) 0.38216(5) 0.03234(13) 0.0358(2) Uani d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.01662(14) 0.01580(13) 0.01640(14) -0.00082(11) 0.00406(11) -0.00067(12) O2 0.0234(5) 0.0239(5) 0.0219(5) -0.0038(4) 0.0101(4) -0.0026(4) O3 0.0219(5) 0.0198(5) 0.0212(5) 0.0015(4) 0.0015(4) 0.0019(4) C4 0.0173(5) 0.0169(5) 0.0170(5) -0.0016(5) 0.0049(5) -0.0026(5) C5 0.0145(5) 0.0158(5) 0.0140(5) 0.0000(5) 0.0018(5) -0.0016(5) C6 0.0200(5) 0.0162(5) 0.0156(5) -0.0015(5) 0.0038(5) -0.0018(5) C7 0.0214(7) 0.0207(7) 0.0285(8) -0.0032(5) 0.0094(5) -0.0047(5) C8 0.0264(7) 0.0283(8) 0.0270(7) -0.0097(5) 0.0097(5) -0.0036(5) C9 0.0372(8) 0.0167(7) 0.0206(7) -0.0084(5) 0.0036(5) -0.0009(5) C10 0.0317(8) 0.0175(7) 0.0263(8) 0.0030(5) 0.0060(5) -0.0024(5) C11 0.0209(7) 0.0212(7) 0.0222(7) 0.0004(5) 0.0062(5) -0.0027(5) F12 0.0529(7) 0.0195(5) 0.0413(5) -0.0123(4) 0.0133(5) 0.0001(4) C13 0.0170(5) 0.0161(5) 0.0168(5) -0.0021(5) 0.0030(5) -0.0011(5) C14 0.0204(7) 0.0206(7) 0.0287(8) -0.0006(5) 0.0094(5) -0.0034(5) C15 0.0292(8) 0.0162(7) 0.0354(8) 0.0010(5) 0.0104(7) -0.0039(5) C16 0.0237(7) 0.0184(7) 0.0270(7) -0.0061(5) 0.0037(5) 0.0006(5) C17 0.0194(7) 0.0253(7) 0.0217(7) -0.0031(5) 0.0057(5) 0.0013(5) C18 0.0194(5) 0.0194(5) 0.0198(7) 0.0016(5) 0.0054(5) -0.0014(5) F19 0.0392(5) 0.0202(5) 0.0582(7) -0.0102(4) 0.0194(5) 0.0000(4) S21 0.02023(14) 0.01628(13) 0.01654(14) -0.00260(12) 0.00672(12) 0.00048(12) O22 0.0315(5) 0.0240(5) 0.0301(5) -0.0094(4) 0.0193(5) -0.0063(4) O23 0.0301(5) 0.0190(5) 0.0202(5) -0.0028(4) -0.0007(4) 0.0037(4) C24 0.0164(5) 0.0179(5) 0.0155(5) -0.0002(5) 0.0040(5) -0.0001(5) C25 0.0200(5) 0.0199(5) 0.0174(7) -0.0009(5) 0.0078(5) -0.0016(5) C26 0.0176(5) 0.0177(5) 0.0161(5) -0.0013(5) 0.0045(5) -0.0021(5) C27 0.0176(5) 0.0198(5) 0.0208(7) 0.0006(5) 0.0044(5) -0.0037(5) C28 0.0172(5) 0.0270(7) 0.0233(7) -0.0043(5) 0.0064(5) -0.0055(5) C29 0.0273(7) 0.0175(7) 0.0246(7) -0.0076(5) 0.0070(5) -0.0036(5) C30 0.0251(7) 0.0173(5) 0.0264(8) 0.0006(5) 0.0056(5) -0.0023(5) C31 0.0188(5) 0.0185(5) 0.0254(7) -0.0002(5) 0.0062(5) -0.0019(5) F32 0.0337(5) 0.0208(5) 0.0492(5) -0.0107(4) 0.0140(5) -0.0028(4) C33 0.0207(5) 0.0153(5) 0.0169(5) -0.0016(5) 0.0070(5) -0.0001(5) C34 0.0201(5) 0.0207(7) 0.0229(7) 0.0017(5) 0.0067(5) 0.0006(5) C35 0.0313(8) 0.0171(5) 0.0245(7) 0.0054(5) 0.0087(5) 0.0024(5) C36 0.0344(8) 0.0145(5) 0.0225(7) -0.0041(5) 0.0133(5) 0.0008(5) C37 0.0214(5) 0.0234(7) 0.0260(7) -0.0053(5) 0.0089(5) -0.0004(5) C38 0.0200(5) 0.0185(5) 0.0252(7) 0.0009(5) 0.0068(5) 0.0009(5) F39 0.0497(5) 0.0170(4) 0.0450(5) -0.0091(4) 0.0214(5) 0.0031(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O2 . 1.4433(11) ? S1 O3 . 1.4497(10) ? S1 C13 . 1.7699(14) ? S1 C4 . 1.8102(14) ? C4 C6 . 1.5147(18) ? C4 C5 . 1.5598(18) ? C4 H4 . 1.0 ? C5 H5A . 0.98 ? C5 H5B . 0.98 ? C5 H5C . 0.98 ? C6 C7 . 1.398(2) ? C6 C11 . 1.398(2) ? C7 C8 . 1.392(2) ? C7 H7 . 0.95 ? C8 C9 . 1.372(2) ? C8 H8 . 0.95 ? C9 F12 . 1.3594(17) ? C9 C10 . 1.376(2) ? C10 C11 . 1.394(2) ? C10 H10 . 0.95 ? C11 H11 . 0.95 ? C13 C14 . 1.389(2) ? C13 C18 . 1.396(2) ? C14 C15 . 1.392(2) ? C14 H14 . 0.95 ? C15 C16 . 1.374(2) ? C15 H15 . 0.95 ? C16 F19 . 1.3578(17) ? C16 C17 . 1.377(2) ? C17 C18 . 1.387(2) ? C17 H17 . 0.95 ? C18 H18 . 0.95 ? S21 O23 . 1.4397(11) ? S21 O22 . 1.4454(11) ? S21 C33 . 1.7661(14) ? S21 C24 . 1.8025(14) ? C24 C26 . 1.5148(18) ? C24 C25 . 1.548(2) ? C24 H24 . 1.0 ? C25 H25A . 0.98 ? C25 H25B . 0.98 ? C25 H25C . 0.98 ? C26 C27 . 1.398(2) ? C26 C31 . 1.399(2) ? C27 C28 . 1.392(2) ? C27 H27 . 0.95 ? C28 C29 . 1.374(2) ? C28 H28 . 0.95 ? C29 F32 . 1.3661(17) ? C29 C30 . 1.379(2) ? C30 C31 . 1.398(2) ? C30 H30 . 0.95 ? C31 H31 . 0.95 ? C33 C38 . 1.391(2) ? C33 C34 . 1.396(2) ? C34 C35 . 1.389(2) ? C34 H34 . 0.95 ? C35 C36 . 1.383(2) ? C35 H35 . 0.95 ? C36 F39 . 1.3506(16) ? C36 C37 . 1.380(2) ? C37 C38 . 1.390(2) ? C37 H37 . 0.95 ? C38 H38 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 S1 O3 . . 118.47(7) ? O2 S1 C13 . . 108.12(6) ? O3 S1 C13 . . 107.84(6) ? O2 S1 C4 . . 108.98(6) ? O3 S1 C4 . . 107.47(6) ? C13 S1 C4 . . 105.19(6) ? C6 C4 C5 . . 116.00(11) ? C6 C4 S1 . . 106.68(9) ? C5 C4 S1 . . 110.14(9) ? C6 C4 H4 . . 107.9 ? C5 C4 H4 . . 107.9 ? S1 C4 H4 . . 107.9 ? C4 C5 H5A . . 109.5 ? C4 C5 H5B . . 109.5 ? H5A C5 H5B . . 109.5 ? C4 C5 H5C . . 109.5 ? H5A C5 H5C . . 109.5 ? H5B C5 H5C . . 109.5 ? C7 C6 C11 . . 119.05(13) ? C7 C6 C4 . . 121.57(13) ? C11 C6 C4 . . 119.35(13) ? C8 C7 C6 . . 120.44(14) ? C8 C7 H7 . . 119.8 ? C6 C7 H7 . . 119.8 ? C9 C8 C7 . . 118.54(14) ? C9 C8 H8 . . 120.7 ? C7 C8 H8 . . 120.7 ? F12 C9 C8 . . 118.31(15) ? F12 C9 C10 . . 118.55(15) ? C8 C9 C10 . . 123.14(14) ? C9 C10 C11 . . 118.01(14) ? C9 C10 H10 . . 121.0 ? C11 C10 H10 . . 121.0 ? C10 C11 C6 . . 120.80(14) ? C10 C11 H11 . . 119.6 ? C6 C11 H11 . . 119.6 ? C14 C13 C18 . . 121.33(13) ? C14 C13 S1 . . 119.16(11) ? C18 C13 S1 . . 119.51(11) ? C13 C14 C15 . . 119.33(14) ? C13 C14 H14 . . 120.3 ? C15 C14 H14 . . 120.3 ? C16 C15 C14 . . 118.06(14) ? C16 C15 H15 . . 121.0 ? C14 C15 H15 . . 121.0 ? F19 C16 C15 . . 118.19(14) ? F19 C16 C17 . . 117.95(14) ? C15 C16 C17 . . 123.85(14) ? C16 C17 C18 . . 118.07(14) ? C16 C17 H17 . . 121.0 ? C18 C17 H17 . . 121.0 ? C17 C18 C13 . . 119.36(13) ? C17 C18 H18 . . 120.3 ? C13 C18 H18 . . 120.3 ? O23 S21 O22 . . 119.10(7) ? O23 S21 C33 . . 108.49(7) ? O22 S21 C33 . . 106.83(7) ? O23 S21 C24 . . 108.76(6) ? O22 S21 C24 . . 107.36(7) ? C33 S21 C24 . . 105.49(6) ? C26 C24 C25 . . 115.07(11) ? C26 C24 S21 . . 106.88(9) ? C25 C24 S21 . . 110.48(9) ? C26 C24 H24 . . 108.1 ? C25 C24 H24 . . 108.1 ? S21 C24 H24 . . 108.1 ? C24 C25 H25A . . 109.5 ? C24 C25 H25B . . 109.5 ? H25A C25 H25B . . 109.5 ? C24 C25 H25C . . 109.5 ? H25A C25 H25C . . 109.5 ? H25B C25 H25C . . 109.5 ? C27 C26 C31 . . 119.23(13) ? C27 C26 C24 . . 119.42(12) ? C31 C26 C24 . . 121.32(12) ? C28 C27 C26 . . 121.06(13) ? C28 C27 H27 . . 119.5 ? C26 C27 H27 . . 119.5 ? C29 C28 C27 . . 117.64(13) ? C29 C28 H28 . . 121.2 ? C27 C28 H28 . . 121.2 ? F32 C29 C28 . . 118.45(13) ? F32 C29 C30 . . 117.76(14) ? C28 C29 C30 . . 123.79(14) ? C29 C30 C31 . . 117.90(14) ? C29 C30 H30 . . 121.0 ? C31 C30 H30 . . 121.0 ? C30 C31 C26 . . 120.36(13) ? C30 C31 H31 . . 119.8 ? C26 C31 H31 . . 119.8 ? C38 C33 C34 . . 121.26(13) ? C38 C33 S21 . . 119.40(10) ? C34 C33 S21 . . 119.31(11) ? C35 C34 C33 . . 119.54(13) ? C35 C34 H34 . . 120.2 ? C33 C34 H34 . . 120.2 ? C36 C35 C34 . . 117.72(13) ? C36 C35 H35 . . 121.1 ? C34 C35 H35 . . 121.1 ? F39 C36 C37 . . 118.01(14) ? F39 C36 C35 . . 117.92(13) ? C37 C36 C35 . . 124.06(13) ? C36 C37 C38 . . 117.76(13) ? C36 C37 H37 . . 121.1 ? C38 C37 H37 . . 121.1 ? C37 C38 C33 . . 119.65(13) ? C37 C38 H38 . . 120.2 ? C33 C38 H38 . . 120.2 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 S1 C4 C6 . . . . 72.07(10) ? O3 S1 C4 C6 . . . . -57.48(10) ? C13 S1 C4 C6 . . . . -172.20(9) ? O2 S1 C4 C5 . . . . -54.61(11) ? O3 S1 C4 C5 . . . . 175.84(9) ? C13 S1 C4 C5 . . . . 61.12(10) ? C5 C4 C6 C7 . . . . 45.20(18) ? S1 C4 C6 C7 . . . . -77.90(14) ? C5 C4 C6 C11 . . . . -136.87(13) ? S1 C4 C6 C11 . . . . 100.03(13) ? C11 C6 C7 C8 . . . . -0.4(2) ? C4 C6 C7 C8 . . . . 177.50(14) ? C6 C7 C8 C9 . . . . 0.4(2) ? C7 C8 C9 F12 . . . . -179.72(14) ? C7 C8 C9 C10 . . . . 0.6(2) ? F12 C9 C10 C11 . . . . 178.78(13) ? C8 C9 C10 C11 . . . . -1.5(2) ? C9 C10 C11 C6 . . . . 1.5(2) ? C7 C6 C11 C10 . . . . -0.5(2) ? C4 C6 C11 C10 . . . . -178.52(13) ? O2 S1 C13 C14 . . . . 6.81(14) ? O3 S1 C13 C14 . . . . 136.03(12) ? C4 S1 C13 C14 . . . . -109.50(12) ? O2 S1 C13 C18 . . . . -173.09(11) ? O3 S1 C13 C18 . . . . -43.88(13) ? C4 S1 C13 C18 . . . . 70.59(12) ? C18 C13 C14 C15 . . . . 0.0(2) ? S1 C13 C14 C15 . . . . -179.91(12) ? C13 C14 C15 C16 . . . . -0.7(2) ? C14 C15 C16 F19 . . . . -178.14(14) ? C14 C15 C16 C17 . . . . 1.0(2) ? F19 C16 C17 C18 . . . . 178.71(13) ? C15 C16 C17 C18 . . . . -0.4(2) ? C16 C17 C18 C13 . . . . -0.4(2) ? C14 C13 C18 C17 . . . . 0.6(2) ? S1 C13 C18 C17 . . . . -179.51(11) ? O23 S21 C24 C26 . . . . -67.08(10) ? O22 S21 C24 C26 . . . . 63.03(10) ? C33 S21 C24 C26 . . . . 176.70(9) ? O23 S21 C24 C25 . . . . 58.79(11) ? O22 S21 C24 C25 . . . . -171.10(9) ? C33 S21 C24 C25 . . . . -57.42(11) ? C25 C24 C26 C27 . . . . 146.61(13) ? S21 C24 C26 C27 . . . . -90.32(13) ? C25 C24 C26 C31 . . . . -35.23(18) ? S21 C24 C26 C31 . . . . 87.83(14) ? C31 C26 C27 C28 . . . . 0.3(2) ? C24 C26 C27 C28 . . . . 178.53(13) ? C26 C27 C28 C29 . . . . 0.2(2) ? C27 C28 C29 F32 . . . . -179.42(13) ? C27 C28 C29 C30 . . . . -0.1(2) ? F32 C29 C30 C31 . . . . 178.71(14) ? C28 C29 C30 C31 . . . . -0.6(2) ? C29 C30 C31 C26 . . . . 1.2(2) ? C27 C26 C31 C30 . . . . -1.1(2) ? C24 C26 C31 C30 . . . . -179.23(13) ? O23 S21 C33 C38 . . . . -15.37(14) ? O22 S21 C33 C38 . . . . -144.93(12) ? C24 S21 C33 C38 . . . . 101.03(12) ? O23 S21 C33 C34 . . . . 162.85(12) ? O22 S21 C33 C34 . . . . 33.29(13) ? C24 S21 C33 C34 . . . . -80.75(13) ? C38 C33 C34 C35 . . . . 0.2(2) ? S21 C33 C34 C35 . . . . -178.02(11) ? C33 C34 C35 C36 . . . . 0.7(2) ? C34 C35 C36 F39 . . . . 178.16(13) ? C34 C35 C36 C37 . . . . -1.2(2) ? F39 C36 C37 C38 . . . . -178.59(13) ? C35 C36 C37 C38 . . . . 0.8(2) ? C36 C37 C38 C33 . . . . 0.1(2) ? C34 C33 C38 C37 . . . . -0.6(2) ? S21 C33 C38 C37 . . . . 177.58(11) ? #===END============================================================== data_compound_11 _database_code_depnum_ccdc_archive 'CCDC 759283' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 N O5 S' _chemical_formula_sum 'C14 H13 N O5 S' _chemical_formula_weight 307.31 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 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.13970(10) _cell_length_b 10.62070(10) _cell_length_c 24.9841(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1363.81(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1858 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9872 _exptl_absorpt_process_details 'SADABS V2.10(Sheldrick, G.M., 2003)' _exptl_special_details ; The transmission factors above are based on the crystal size, using SHELXL-97. The output from SADABS has a ratio of minimum to maximum apparent transmission of 0.8536. absolute configuration test conclusive. correct enantiomer R1=0.0280, wR2=0.0840 incorrect enantiomer R1=0.0296, wR2=0.0878 refining in SHELXL-97 using TWIN,BASF refined to 0.00001 for the correct enantiomer. ; _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 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17154 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.44 _reflns_number_total 3108 _reflns_number_gt 2978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0476P)^2^+0.1765P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(6) _chemical_absolute_configuration ad _refine_ls_number_reflns 3108 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.207 _refine_ls_restrained_S_all 1.207 _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 C1 C 0.2845(3) 0.25406(14) 0.33976(6) 0.0152(3) Uani 1 1 d . . . C2 C 0.4355(3) 0.34174(15) 0.36856(6) 0.0169(3) Uani 1 1 d . . . C3 C 0.4000(3) 0.35062(16) 0.42375(7) 0.0208(3) Uani 1 1 d . . . H3 H 0.5037 0.4069 0.4442 0.025 Uiso 1 1 calc R . . C4 C 0.2131(3) 0.27710(16) 0.44872(6) 0.0217(3) Uani 1 1 d . . . H4 H 0.1898 0.2840 0.4863 0.026 Uiso 1 1 calc R . . C5 C 0.0598(3) 0.19388(16) 0.42011(7) 0.0219(4) Uani 1 1 d . . . H5 H -0.0685 0.1447 0.4378 0.026 Uiso 1 1 calc R . . C6 C 0.0955(3) 0.18297(15) 0.36514(7) 0.0188(3) Uani 1 1 d . . . H6 H -0.0098 0.1267 0.3450 0.023 Uiso 1 1 calc R . . O7 O 0.6043(2) 0.41262(11) 0.33994(4) 0.0219(3) Uani 1 1 d . . . C8 C 0.7512(4) 0.50639(17) 0.36812(7) 0.0266(4) Uani 1 1 d . . . H8A H 0.6318 0.5662 0.3851 0.040 Uiso 1 1 calc R . . H8B H 0.8639 0.5513 0.3429 0.040 Uiso 1 1 calc R . . H8C H 0.8582 0.4657 0.3956 0.040 Uiso 1 1 calc R . . S9 S 0.31919(7) 0.23437(4) 0.269716(14) 0.01482(10) Uani 1 1 d . . . O10 O 0.1669(3) 0.12599(10) 0.25473(4) 0.0202(3) Uani 1 1 d . . . O11 O 0.5906(2) 0.23421(12) 0.25499(4) 0.0211(3) Uani 1 1 d . . . C12 C 0.1665(3) 0.37277(15) 0.24370(6) 0.0174(3) Uani 1 1 d . . . H12A H -0.0198 0.3735 0.2538 0.021 Uiso 1 1 calc R . . H12B H 0.2497 0.4486 0.2591 0.021 Uiso 1 1 calc R . . C13 C 0.1919(3) 0.37498(14) 0.18358(6) 0.0160(3) Uani 1 1 d . . . C14 C 0.3984(3) 0.43849(15) 0.15991(7) 0.0189(3) Uani 1 1 d . . . H14 H 0.5241 0.4791 0.1818 0.023 Uiso 1 1 calc R . . C15 C 0.4231(3) 0.44315(16) 0.10464(7) 0.0192(3) Uani 1 1 d . . . H15 H 0.5627 0.4874 0.0883 0.023 Uiso 1 1 calc R . . C16 C 0.2382(3) 0.38137(15) 0.07403(6) 0.0179(3) Uani 1 1 d . . . C17 C 0.0316(3) 0.31561(15) 0.09617(6) 0.0186(3) Uani 1 1 d . . . H17 H -0.0912 0.2737 0.0741 0.022 Uiso 1 1 calc R . . C18 C 0.0091(3) 0.31267(15) 0.15146(7) 0.0178(3) Uani 1 1 d . . . H18 H -0.1308 0.2683 0.1676 0.021 Uiso 1 1 calc R . . N19 N 0.2606(3) 0.38872(13) 0.01516(6) 0.0217(3) Uani 1 1 d . . . O20 O 0.4501(3) 0.44295(13) -0.00364(5) 0.0320(3) Uani 1 1 d . . . O21 O 0.0885(3) 0.34069(13) -0.01209(5) 0.0289(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 C1 0.0170(6) 0.0152(7) 0.0133(7) 0.0009(6) -0.0020(6) 0.0013(6) C2 0.0159(7) 0.0182(8) 0.0167(8) 0.0018(6) -0.0011(6) -0.0017(6) C3 0.0232(8) 0.0228(8) 0.0164(8) -0.0015(6) -0.0029(7) -0.0027(7) C4 0.0257(8) 0.0256(8) 0.0138(7) 0.0003(6) 0.0014(6) 0.0003(7) C5 0.0236(8) 0.0202(8) 0.0218(8) 0.0003(6) 0.0068(7) -0.0033(7) C6 0.0185(7) 0.0172(8) 0.0207(8) -0.0029(6) 0.0011(6) -0.0009(6) O7 0.0262(6) 0.0239(6) 0.0155(5) 0.0001(4) -0.0007(5) -0.0120(5) C8 0.0325(10) 0.0258(9) 0.0216(8) -0.0014(7) -0.0013(7) -0.0147(8) S9 0.01515(17) 0.01660(18) 0.01271(17) -0.00114(13) -0.00012(14) 0.00146(14) O10 0.0253(6) 0.0178(5) 0.0177(5) -0.0037(4) 0.0000(5) -0.0029(5) O11 0.0158(5) 0.0294(7) 0.0180(5) 0.0003(5) 0.0022(4) 0.0036(5) C12 0.0188(8) 0.0172(7) 0.0161(7) -0.0013(6) -0.0016(6) 0.0026(7) C13 0.0174(7) 0.0147(7) 0.0158(7) -0.0003(6) -0.0015(7) 0.0041(7) C14 0.0183(7) 0.0173(8) 0.0210(8) -0.0005(6) -0.0024(6) 0.0004(6) C15 0.0183(7) 0.0182(8) 0.0212(8) 0.0030(6) 0.0014(6) 0.0006(6) C16 0.0227(8) 0.0180(8) 0.0131(7) 0.0018(6) 0.0001(6) 0.0052(6) C17 0.0197(8) 0.0184(8) 0.0178(8) -0.0018(6) -0.0032(6) 0.0010(7) C18 0.0157(7) 0.0183(7) 0.0196(8) 0.0017(6) 0.0008(6) 0.0020(6) N19 0.0292(8) 0.0201(7) 0.0158(7) 0.0015(5) 0.0029(6) 0.0056(6) O20 0.0401(8) 0.0326(7) 0.0233(7) 0.0054(5) 0.0086(6) -0.0039(6) O21 0.0346(7) 0.0350(7) 0.0170(6) -0.0016(5) -0.0047(5) 0.0011(6) _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 C1 C6 1.384(2) . ? C1 C2 1.410(2) . ? C1 S9 1.7714(15) . ? C2 O7 1.3531(19) . ? C2 C3 1.394(2) . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.383(2) . ? C4 H4 0.9500 . ? C5 C6 1.390(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O7 C8 1.434(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? S9 O10 1.4413(12) . ? S9 O11 1.4427(11) . ? S9 C12 1.7887(16) . ? C12 C13 1.508(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.390(2) . ? C13 C18 1.402(2) . ? C14 C15 1.387(2) . ? C14 H14 0.9500 . ? C15 C16 1.385(2) . ? C15 H15 0.9500 . ? C16 C17 1.386(2) . ? C16 N19 1.478(2) . ? C17 C18 1.386(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? N19 O20 1.2248(19) . ? N19 O21 1.227(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 C6 C1 C2 120.85(14) . . ? C6 C1 S9 117.31(12) . . ? C2 C1 S9 121.80(12) . . ? O7 C2 C3 124.67(14) . . ? O7 C2 C1 116.79(14) . . ? C3 C2 C1 118.53(15) . . ? C4 C3 C2 119.84(15) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 121.47(15) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.24(15) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C1 C6 C5 119.98(15) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C2 O7 C8 117.67(13) . . ? O7 C8 H8A 109.5 . . ? O7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O10 S9 O11 117.25(7) . . ? O10 S9 C1 107.23(7) . . ? O11 S9 C1 110.45(7) . . ? O10 S9 C12 108.88(7) . . ? O11 S9 C12 109.43(8) . . ? C1 S9 C12 102.58(7) . . ? C13 C12 S9 109.68(10) . . ? C13 C12 H12A 109.7 . . ? S9 C12 H12A 109.7 . . ? C13 C12 H12B 109.7 . . ? S9 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C14 C13 C18 119.84(14) . . ? C14 C13 C12 119.83(14) . . ? C18 C13 C12 120.33(14) . . ? C15 C14 C13 120.69(15) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 118.04(15) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? C15 C16 C17 122.95(15) . . ? C15 C16 N19 118.11(15) . . ? C17 C16 N19 118.93(14) . . ? C16 C17 C18 118.22(15) . . ? C16 C17 H17 120.9 . . ? C18 C17 H17 120.9 . . ? C17 C18 C13 120.25(15) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? O20 N19 O21 123.77(15) . . ? O20 N19 C16 117.94(14) . . ? O21 N19 C16 118.29(14) . . ? 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 C6 C1 C2 O7 -176.01(14) . . . . ? S9 C1 C2 O7 1.6(2) . . . . ? C6 C1 C2 C3 3.4(2) . . . . ? S9 C1 C2 C3 -179.06(13) . . . . ? O7 C2 C3 C4 177.15(15) . . . . ? C1 C2 C3 C4 -2.2(2) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C2 C1 C6 C5 -2.6(2) . . . . ? S9 C1 C6 C5 179.72(13) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C3 C2 O7 C8 -2.1(2) . . . . ? C1 C2 O7 C8 177.21(15) . . . . ? C6 C1 S9 O10 -10.81(14) . . . . ? C2 C1 S9 O10 171.53(13) . . . . ? C6 C1 S9 O11 -139.66(12) . . . . ? C2 C1 S9 O11 42.68(15) . . . . ? C6 C1 S9 C12 103.80(13) . . . . ? C2 C1 S9 C12 -73.86(14) . . . . ? O10 S9 C12 C13 -69.76(12) . . . . ? O11 S9 C12 C13 59.57(13) . . . . ? C1 S9 C12 C13 176.84(11) . . . . ? S9 C12 C13 C14 -93.56(15) . . . . ? S9 C12 C13 C18 86.06(16) . . . . ? C18 C13 C14 C15 1.3(2) . . . . ? C12 C13 C14 C15 -179.05(14) . . . . ? C13 C14 C15 C16 -0.9(2) . . . . ? C14 C15 C16 C17 -0.1(2) . . . . ? C14 C15 C16 N19 178.60(14) . . . . ? C15 C16 C17 C18 0.5(2) . . . . ? N19 C16 C17 C18 -178.16(14) . . . . ? C16 C17 C18 C13 0.0(2) . . . . ? C14 C13 C18 C17 -0.9(2) . . . . ? C12 C13 C18 C17 179.50(14) . . . . ? C15 C16 N19 O20 4.1(2) . . . . ? C17 C16 N19 O20 -177.15(15) . . . . ? C15 C16 N19 O21 -175.60(15) . . . . ? C17 C16 N19 O21 3.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.288 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.100 #===END============================================================== data_compound_12 _database_code_depnum_ccdc_archive 'CCDC 759284' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 N O5 S' _chemical_formula_sum 'C14 H13 N O5 S' _chemical_formula_weight 307.31 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 P21/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 13.691(3) _cell_length_b 12.8075(13) _cell_length_c 7.9667(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.450(13) _cell_angle_gamma 90.00 _cell_volume 1394.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6067 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 30.11 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.45768 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Ultra (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini R Ultra' _diffrn_measurement_method 'thin slice \w scans' _diffrn_detector_area_resol_mean 10.2673 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13717 _diffrn_reflns_av_R_equivalents 0.0131 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 30.11 _reflns_number_total 4067 _reflns_number_gt 3598 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0460P)^2^+0.4022P] 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 4067 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 S9 S 0.763895(17) 0.602259(18) 0.06387(3) 0.01395(7) Uani 1 1 d . . . O2 O 0.43259(5) 0.37984(6) 0.33473(10) 0.02120(16) Uani 1 1 d . . . O10 O 0.81898(5) 0.52769(6) -0.02894(9) 0.01929(15) Uani 1 1 d . . . O11 O 0.73031(5) 0.69637(6) -0.02118(9) 0.01963(16) Uani 1 1 d . . . O20 O 1.16063(6) 0.95030(6) -0.02527(11) 0.02376(17) Uani 1 1 d . . . O21 O 1.23633(6) 0.80333(7) -0.05343(12) 0.02777(19) Uani 1 1 d . . . N19 N 1.16697(6) 0.85492(7) -0.00894(11) 0.01771(17) Uani 1 1 d . . . C1 C 0.34607(7) 0.43440(9) 0.37983(13) 0.0204(2) Uani 1 1 d . . . H1A H 0.3636 0.4861 0.4636 0.022(3) Uiso 1 1 d R . . H1B H 0.3009 0.3856 0.4239 0.029(4) Uiso 1 1 d R . . H1C H 0.3160 0.4679 0.2820 0.020(3) Uiso 1 1 d R . . C3 C 0.50479(7) 0.43668(8) 0.27016(12) 0.01690(19) Uani 1 1 d . . . C4 C 0.50039(7) 0.54432(8) 0.24163(13) 0.01850(19) Uani 1 1 d . . . H4 H 0.4446 0.5817 0.2649 0.026(4) Uiso 1 1 d R . . C5 C 0.58020(7) 0.59523(8) 0.17814(13) 0.01778(19) Uani 1 1 d . . . H5 H 0.5780 0.6669 0.1593 0.029(4) Uiso 1 1 d R . . C6 C 0.66340(7) 0.53831(8) 0.14303(12) 0.01540(18) Uani 1 1 d . . . C7 C 0.66755(7) 0.43048(8) 0.16988(13) 0.01798(19) Uani 1 1 d . . . H7 H 0.7232 0.3931 0.1455 0.029(4) Uiso 1 1 d R . . C8 C 0.58846(8) 0.37989(8) 0.23290(14) 0.0199(2) Uani 1 1 d . . . H8 H 0.5907 0.3081 0.2506 0.031(4) Uiso 1 1 d R . . C12 C 0.83932(7) 0.64009(8) 0.24570(12) 0.01625(18) Uani 1 1 d . . . H12A H 0.8029 0.6855 0.3167 0.027(4) Uiso 1 1 d R . . H12B H 0.8594 0.5788 0.3104 0.024(3) Uiso 1 1 d R . . C13 C 0.92796(7) 0.69642(8) 0.18864(11) 0.01464(18) Uani 1 1 d . . . C14 C 0.92779(7) 0.80554(8) 0.17897(12) 0.01547(18) Uani 1 1 d . . . H14 H 0.8746 0.8431 0.2142 0.032(4) Uiso 1 1 d R . . C15 C 1.00677(7) 0.85805(8) 0.11691(12) 0.01601(18) Uani 1 1 d . . . H15 H 1.0070 0.9305 0.1098 0.024(3) Uiso 1 1 d R . . C16 C 1.08548(7) 0.80000(8) 0.06573(12) 0.01506(18) Uani 1 1 d . . . C17 C 1.08908(7) 0.69212(8) 0.07792(12) 0.01688(19) Uani 1 1 d . . . H17 H 1.1434 0.6552 0.0460 0.035(4) Uiso 1 1 d R . . C18 C 1.00924(7) 0.64060(8) 0.13915(12) 0.01709(18) Uani 1 1 d . . . H18 H 1.0098 0.5682 0.1473 0.025(4) 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 S9 0.01504(12) 0.01285(12) 0.01429(11) -0.00029(8) 0.00375(8) -0.00014(8) O2 0.0159(3) 0.0182(4) 0.0301(4) -0.0004(3) 0.0070(3) -0.0032(3) O10 0.0207(3) 0.0175(3) 0.0204(3) -0.0045(3) 0.0071(3) 0.0000(3) O11 0.0205(3) 0.0175(3) 0.0211(3) 0.0055(3) 0.0028(3) 0.0011(3) O20 0.0243(4) 0.0156(4) 0.0322(4) -0.0020(3) 0.0083(3) -0.0035(3) O21 0.0174(4) 0.0241(4) 0.0431(5) -0.0029(3) 0.0121(3) 0.0015(3) N19 0.0157(4) 0.0174(4) 0.0203(4) -0.0032(3) 0.0030(3) -0.0020(3) C1 0.0144(4) 0.0244(5) 0.0228(5) -0.0026(4) 0.0036(4) -0.0024(4) C3 0.0151(4) 0.0168(5) 0.0190(4) -0.0012(3) 0.0022(3) -0.0030(3) C4 0.0149(4) 0.0179(5) 0.0230(5) 0.0003(4) 0.0035(3) 0.0020(3) C5 0.0180(4) 0.0140(4) 0.0216(5) 0.0009(3) 0.0033(4) 0.0018(3) C6 0.0149(4) 0.0146(4) 0.0170(4) -0.0003(3) 0.0030(3) -0.0003(3) C7 0.0166(4) 0.0148(4) 0.0230(5) -0.0009(4) 0.0049(3) 0.0009(3) C8 0.0196(5) 0.0132(4) 0.0273(5) -0.0005(4) 0.0051(4) -0.0004(4) C12 0.0184(4) 0.0170(4) 0.0136(4) -0.0005(3) 0.0033(3) -0.0026(4) C13 0.0159(4) 0.0158(4) 0.0123(4) -0.0005(3) 0.0014(3) -0.0004(3) C14 0.0146(4) 0.0153(4) 0.0166(4) -0.0011(3) 0.0022(3) 0.0013(3) C15 0.0165(4) 0.0135(4) 0.0181(4) -0.0013(3) 0.0017(3) 0.0007(3) C16 0.0136(4) 0.0158(4) 0.0158(4) -0.0008(3) 0.0015(3) -0.0009(3) C17 0.0154(4) 0.0161(4) 0.0193(4) -0.0013(3) 0.0027(3) 0.0028(3) C18 0.0194(5) 0.0134(4) 0.0186(4) 0.0000(3) 0.0024(3) 0.0010(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 S9 O11 1.4442(8) . ? S9 O10 1.4473(7) . ? S9 C6 1.7510(10) . ? S9 C12 1.7943(10) . ? O2 C3 1.3538(12) . ? O2 C1 1.4394(13) . ? O20 N19 1.2311(12) . ? O21 N19 1.2265(12) . ? N19 C16 1.4742(12) . ? C1 H1A 0.9603 . ? C1 H1B 0.9607 . ? C1 H1C 0.9605 . ? C3 C4 1.3980(14) . ? C3 C8 1.4036(14) . ? C4 C5 1.3935(14) . ? C4 H4 0.9297 . ? C5 C6 1.3948(13) . ? C5 H5 0.9304 . ? C6 C7 1.3981(14) . ? C7 C8 1.3820(14) . ? C7 H7 0.9302 . ? C8 H8 0.9306 . ? C12 C13 1.5055(13) . ? C12 H12A 0.9700 . ? C12 H12B 0.9696 . ? C13 C18 1.3991(13) . ? C13 C14 1.3996(14) . ? C14 C15 1.3894(13) . ? C14 H14 0.9302 . ? C15 C16 1.3904(13) . ? C15 H15 0.9298 . ? C16 C17 1.3858(14) . ? C17 C18 1.3902(14) . ? C17 H17 0.9298 . ? C18 H18 0.9297 . ? 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 O11 S9 O10 118.17(5) . . ? O11 S9 C6 108.93(5) . . ? O10 S9 C6 108.68(5) . . ? O11 S9 C12 107.75(5) . . ? O10 S9 C12 107.36(5) . . ? C6 S9 C12 105.19(5) . . ? C3 O2 C1 117.67(8) . . ? O21 N19 O20 123.70(9) . . ? O21 N19 C16 118.53(9) . . ? O20 N19 C16 117.76(8) . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.4 . . ? H1B C1 H1C 109.5 . . ? O2 C3 C4 124.52(9) . . ? O2 C3 C8 115.19(9) . . ? C4 C3 C8 120.29(9) . . ? C5 C4 C3 119.56(9) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 119.73(9) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.2 . . ? C5 C6 C7 120.79(9) . . ? C5 C6 S9 119.78(8) . . ? C7 C6 S9 119.44(8) . . ? C8 C7 C6 119.54(9) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.2 . . ? C7 C8 C3 120.08(9) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 120.0 . . ? C13 C12 S9 108.71(6) . . ? C13 C12 H12A 109.9 . . ? S9 C12 H12A 110.0 . . ? C13 C12 H12B 109.9 . . ? S9 C12 H12B 110.0 . . ? H12A C12 H12B 108.3 . . ? C18 C13 C14 119.56(9) . . ? C18 C13 C12 120.63(9) . . ? C14 C13 C12 119.76(9) . . ? C15 C14 C13 120.28(9) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 118.63(9) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C17 C16 C15 122.52(9) . . ? C17 C16 N19 118.64(9) . . ? C15 C16 N19 118.82(9) . . ? C16 C17 C18 118.19(9) . . ? C16 C17 H17 120.9 . . ? C18 C17 H17 120.9 . . ? C17 C18 C13 120.79(9) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 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 C3 C4 -1.15(15) . . . . ? C1 O2 C3 C8 178.29(9) . . . . ? O2 C3 C4 C5 178.51(10) . . . . ? C8 C3 C4 C5 -0.91(15) . . . . ? C3 C4 C5 C6 0.28(15) . . . . ? C4 C5 C6 C7 0.37(15) . . . . ? C4 C5 C6 S9 -179.80(8) . . . . ? O11 S9 C6 C5 -25.01(10) . . . . ? O10 S9 C6 C5 -155.00(8) . . . . ? C12 S9 C6 C5 90.28(9) . . . . ? O11 S9 C6 C7 154.83(8) . . . . ? O10 S9 C6 C7 24.84(10) . . . . ? C12 S9 C6 C7 -89.88(9) . . . . ? C5 C6 C7 C8 -0.39(15) . . . . ? S9 C6 C7 C8 179.78(8) . . . . ? C6 C7 C8 C3 -0.24(16) . . . . ? O2 C3 C8 C7 -178.57(9) . . . . ? C4 C3 C8 C7 0.89(16) . . . . ? O11 S9 C12 C13 -63.69(8) . . . . ? O10 S9 C12 C13 64.58(8) . . . . ? C6 S9 C12 C13 -179.79(7) . . . . ? S9 C12 C13 C18 -82.95(10) . . . . ? S9 C12 C13 C14 94.67(10) . . . . ? C18 C13 C14 C15 1.53(14) . . . . ? C12 C13 C14 C15 -176.11(8) . . . . ? C13 C14 C15 C16 -0.26(14) . . . . ? C14 C15 C16 C17 -1.53(14) . . . . ? C14 C15 C16 N19 176.64(8) . . . . ? O21 N19 C16 C17 -1.95(14) . . . . ? O20 N19 C16 C17 177.00(9) . . . . ? O21 N19 C16 C15 179.80(9) . . . . ? O20 N19 C16 C15 -1.24(13) . . . . ? C15 C16 C17 C18 1.97(15) . . . . ? N19 C16 C17 C18 -176.20(8) . . . . ? C16 C17 C18 C13 -0.64(14) . . . . ? C14 C13 C18 C17 -1.07(14) . . . . ? C12 C13 C18 C17 176.55(9) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 30.11 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.362 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.048 #===END============================================================== data_compound_15 _database_code_depnum_ccdc_archive 'CCDC 759285' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C14 H14 O2 S' _chemical_formula_sum 'C14 H14 O2 S' _chemical_formula_iupac ? _chemical_formula_weight 246.31 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 n 1' _symmetry_space_group_name_Hall ' P -2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 7.4697(8) _cell_length_b 5.6810(7) _cell_length_c 14.0467(16) _cell_angle_alpha 90 _cell_angle_beta 91.800(2) _cell_angle_gamma 90 _cell_volume 595.78(12) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1903 _cell_measurement_theta_min 2.9017 _cell_measurement_theta_max 27.9493 _cell_measurement_temperature 100.(2) _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs Version 2008/1' _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX DUO' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 6696 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.30 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _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. ; _reflns_number_total 2936 _reflns_number_gt 2702 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_gt 0.0786 _refine_ls_wR_factor_ref 0.0810 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_number_reflns 2936 _refine_ls_number_parameters 155 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.0448P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.414 _refine_diff_density_min -0.253 _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 0.003(63) _chemical_absolute_configuration ad 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' 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' _computing_data_collection 'Bruker Instrument Service v2009, 7, 0, 0' _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL--97; PLATON' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.78629(5) 0.39155(8) 0.34307(3) 0.01734(11) Uani d . 1 . . O O2 0.8083(2) 0.6399(2) 0.32578(11) 0.0295(4) Uani d . 1 . . O O3 0.61706(18) 0.2833(2) 0.31733(10) 0.0265(4) Uani d . 1 . . C C4 0.8329(2) 0.3371(4) 0.46521(12) 0.0153(4) Uani d . 1 . . C C5 0.7774(2) 0.1250(4) 0.50475(13) 0.0181(4) Uani d . 1 . . H H5 0.7142 0.0119 0.4669 0.022 Uiso calc R 1 . . C C6 0.8165(2) 0.0822(4) 0.60055(14) 0.0221(4) Uani d . 1 . . H H6 0.7794 -0.061 0.6287 0.027 Uiso calc R 1 . . C C7 0.9095(2) 0.2479(4) 0.65513(13) 0.0232(5) Uani d . 1 . . H H7 0.9367 0.2165 0.7204 0.028 Uiso calc R 1 . . C C8 0.9631(2) 0.4590(4) 0.61544(13) 0.0219(4) Uani d . 1 . . H H8 1.0255 0.5721 0.6537 0.026 Uiso calc R 1 . . C C9 0.9255(2) 0.5048(4) 0.51981(13) 0.0188(4) Uani d . 1 . . H H9 0.9624 0.6485 0.492 0.023 Uiso calc R 1 . . C C10 0.9613(2) 0.2332(4) 0.28326(12) 0.0169(4) Uani d . 1 . . H H10 0.9619 0.0679 0.3077 0.02 Uiso calc R 1 . . C C11 1.1433(2) 0.3417(4) 0.30954(14) 0.0247(5) Uani d . 1 . . H H11A 1.2384 0.2468 0.2821 0.037 Uiso calc R 1 . . H H11B 1.1598 0.3456 0.379 0.037 Uiso calc R 1 . . H H11C 1.1484 0.5024 0.2843 0.037 Uiso calc R 1 . . C C12 0.9151(2) 0.2239(2) 0.17740(12) 0.0155(4) Uani d . 1 . . C C13 0.9622(2) 0.4032(4) 0.11515(13) 0.0178(4) Uani d . 1 . . H H13 1.0219 0.5395 0.1392 0.021 Uiso calc R 1 . . C C14 0.9225(2) 0.3835(4) 0.01841(13) 0.0188(4) Uani d . 1 . . H H14 0.9557 0.506 -0.0235 0.023 Uiso calc R 1 . . C C15 0.8345(2) 0.1862(4) -0.01751(13) 0.0209(4) Uani d . 1 . . H H15 0.8092 0.1717 -0.084 0.025 Uiso calc R 1 . . C C16 0.7833(2) 0.0088(4) 0.04488(14) 0.0207(4) Uani d . 1 . . H H16 0.7205 -0.1252 0.021 0.025 Uiso calc R 1 . . C C17 0.8238(2) 0.0278(4) 0.14112(13) 0.0181(4) Uani d . 1 . . H H17 0.789 -0.0939 0.1831 0.022 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0184(2) 0.0204(2) 0.0132(2) 0.0038(2) 0.00095(14) 0.0019(2) O2 0.0452(10) 0.0223(8) 0.0213(9) 0.0106(7) 0.0056(7) 0.0060(5) O3 0.0164(7) 0.0459(10) 0.0170(7) 0.0039(7) -0.0009(5) 0.0000(7) C4 0.0124(8) 0.0229(10) 0.0106(8) 0.0036(7) 0.0008(7) 0.0004(8) C5 0.0159(9) 0.0206(11) 0.0179(10) -0.0009(8) 0.0013(7) 0.0002(8) C6 0.0215(10) 0.0229(11) 0.0222(10) 0.0034(8) 0.0056(8) 0.0069(9) C7 0.0228(10) 0.0332(13) 0.0139(9) 0.0093(9) 0.0027(8) 0.0006(8) C8 0.0152(9) 0.0305(11) 0.0199(10) 0.0029(8) -0.0019(8) -0.0072(9) C9 0.0169(9) 0.0183(10) 0.0212(10) 0.0022(8) 0.0029(7) -0.0019(8) C10 0.0178(9) 0.0190(10) 0.0139(9) 0.0027(8) 0.0008(7) 0.0002(7) C11 0.0186(9) 0.0390(13) 0.0165(10) -0.0033(9) -0.0004(8) -0.0012(9) C12 0.0135(8) 0.0173(10) 0.0157(9) 0.0015(7) 0.0002(7) -0.0008(7) C13 0.0143(9) 0.0191(10) 0.0199(9) -0.0010(8) 0.0006(7) 0.0004(8) C14 0.0158(9) 0.0232(10) 0.0176(9) 0.0012(8) 0.0030(7) 0.0052(8) C15 0.0191(10) 0.0295(11) 0.0141(9) 0.0043(8) 0.0013(8) -0.0001(8) C16 0.0221(10) 0.0196(11) 0.0205(10) -0.0012(8) -0.0008(8) -0.0032(8) C17 0.0196(9) 0.0184(10) 0.0165(9) 0.0006(8) 0.0031(7) 0.0028(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O3 . 1.4415(15) ? S1 O2 . 1.4419(15) ? S1 C4 . 1.767(2) ? S1 C10 . 1.815(2) ? C4 C9 . 1.393(3) ? C4 C5 . 1.395(3) ? C5 C6 . 1.389(3) ? C5 H5 . 0.95 ? C6 C7 . 1.387(3) ? C6 H6 . 0.95 ? C7 C8 . 1.387(3) ? C7 H7 . 0.95 ? C8 C9 . 1.388(3) ? C8 H8 . 0.95 ? C9 H9 . 0.95 ? C10 C12 . 1.517(3) ? C10 C11 . 1.527(3) ? C10 H10 . 1.0 ? C11 H11A . 0.98 ? C11 H11B . 0.98 ? C11 H11C . 0.98 ? C12 C17 . 1.394(3) ? C12 C13 . 1.395(3) ? C13 C14 . 1.386(3) ? C13 H13 . 0.95 ? C14 C15 . 1.387(3) ? C14 H14 . 0.95 ? C15 C16 . 1.397(3) ? C15 H15 . 0.95 ? C16 C17 . 1.380(3) ? C16 H16 . 0.95 ? C17 H17 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 S1 O2 . . 118.62(10) ? O3 S1 C4 . . 108.26(9) ? O2 S1 C4 . . 108.34(10) ? O3 S1 C10 . . 108.14(9) ? O2 S1 C10 . . 108.62(9) ? C4 S1 C10 . . 103.88(9) ? C9 C4 C5 . . 121.33(18) ? C9 C4 S1 . . 119.61(15) ? C5 C4 S1 . . 119.06(15) ? C6 C5 C4 . . 118.7(2) ? C6 C5 H5 . . 120.6 ? C4 C5 H5 . . 120.6 ? C7 C6 C5 . . 120.2(2) ? C7 C6 H6 . . 119.9 ? C5 C6 H6 . . 119.9 ? C6 C7 C8 . . 120.7(2) ? C6 C7 H7 . . 119.6 ? C8 C7 H7 . . 119.6 ? C7 C8 C9 . . 119.9(2) ? C7 C8 H8 . . 120.0 ? C9 C8 H8 . . 120.0 ? C8 C9 C4 . . 119.1(2) ? C8 C9 H9 . . 120.5 ? C4 C9 H9 . . 120.5 ? C12 C10 C11 . . 115.11(16) ? C12 C10 S1 . . 109.03(13) ? C11 C10 S1 . . 109.67(14) ? C12 C10 H10 . . 107.6 ? C11 C10 H10 . . 107.6 ? S1 C10 H10 . . 107.6 ? C10 C11 H11A . . 109.5 ? C10 C11 H11B . . 109.5 ? H11A C11 H11B . . 109.5 ? C10 C11 H11C . . 109.5 ? H11A C11 H11C . . 109.5 ? H11B C11 H11C . . 109.5 ? C17 C12 C13 . . 118.97(18) ? C17 C12 C10 . . 118.68(17) ? C13 C12 C10 . . 122.35(17) ? C14 C13 C12 . . 120.4(2) ? C14 C13 H13 . . 119.8 ? C12 C13 H13 . . 119.8 ? C13 C14 C15 . . 120.4(2) ? C13 C14 H14 . . 119.8 ? C15 C14 H14 . . 119.8 ? C14 C15 C16 . . 119.40(18) ? C14 C15 H15 . . 120.3 ? C16 C15 H15 . . 120.3 ? C17 C16 C15 . . 120.1(2) ? C17 C16 H16 . . 119.9 ? C15 C16 H16 . . 119.9 ? C16 C17 C12 . . 120.7(2) ? C16 C17 H17 . . 119.7 ? C12 C17 H17 . . 119.7 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O3 S1 C4 C9 . . . . -146.85(15) ? O2 S1 C4 C9 . . . . -17.01(18) ? C10 S1 C4 C9 . . . . 98.36(16) ? O3 S1 C4 C5 . . . . 33.82(17) ? O2 S1 C4 C5 . . . . 163.67(15) ? C10 S1 C4 C5 . . . . -80.96(16) ? C9 C4 C5 C6 . . . . -0.1(3) ? S1 C4 C5 C6 . . . . 179.21(15) ? C4 C5 C6 C7 . . . . -0.2(3) ? C5 C6 C7 C8 . . . . 0.7(3) ? C6 C7 C8 C9 . . . . -0.8(3) ? C7 C8 C9 C4 . . . . 0.4(3) ? C5 C4 C9 C8 . . . . 0.0(3) ? S1 C4 C9 C8 . . . . -179.29(14) ? O3 S1 C10 C12 . . . . 53.61(16) ? O2 S1 C10 C12 . . . . -76.35(15) ? C4 S1 C10 C12 . . . . 168.47(14) ? O3 S1 C10 C11 . . . . -179.52(14) ? O2 S1 C10 C11 . . . . 50.52(16) ? C4 S1 C10 C11 . . . . -64.65(15) ? C11 C10 C12 C17 . . . . 142.3(2) ? S1 C10 C12 C17 . . . . -94.0(2) ? C11 C10 C12 C13 . . . . -37.0(3) ? S1 C10 C12 C13 . . . . 86.7(2) ? C17 C12 C13 C14 . . . . -1.5(3) ? C10 C12 C13 C14 . . . . 177.83(17) ? C12 C13 C14 C15 . . . . 0.4(3) ? C13 C14 C15 C16 . . . . 1.1(3) ? C14 C15 C16 C17 . . . . -1.5(3) ? C15 C16 C17 C12 . . . . 0.3(3) ? C13 C12 C17 C16 . . . . 1.2(3) ? C10 C12 C17 C16 . . . . -178.21(17) ? #===END============================================================== data_compound_16 _database_code_depnum_ccdc_archive 'CCDC 759286' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O4 S' _chemical_formula_sum 'C16 H18 O4 S' _chemical_formula_weight 306.36 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' 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.0952(3) _cell_length_b 12.2671(5) _cell_length_c 8.6368(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.274(2) _cell_angle_gamma 90.00 _cell_volume 749.64(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8916 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.899 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The 0 0 1, 0 1 1, 0 2 0 and 0 0 2 reflections have been omitted due to the beamstop. absolute configuration test conclusive. correct enantiomer R1=0.0318, wR2=0.0809 incorrect enantiomer R1=0.0334, wR2=0.0849 refining in SHELXL-97 using TWIN,BASF refined to 0.00001 for the correct enantiomer. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6258 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3212 _reflns_number_gt 3052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL--97; PLATON' _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^)+(0.0351P)^2^+0.1455P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(6) _chemical_absolute_configuration ad _refine_ls_number_reflns 3212 _refine_ls_number_parameters 193 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 0.3682(3) 0.2750(2) 1.1508(2) 0.0409(5) Uani 1 1 d . . . H1A H 0.3572 0.3320 1.2291 0.061 Uiso 1 1 calc R . . H1B H 0.4893 0.2372 1.1703 0.061 Uiso 1 1 calc R . . H1C H 0.2646 0.2227 1.1564 0.061 Uiso 1 1 calc R . . O2 O 0.35894(19) 0.32343(11) 0.99926(15) 0.0320(3) Uani 1 1 d . . . C3 C 0.3635(2) 0.25613(16) 0.8758(2) 0.0266(4) Uani 1 1 d . . . C4 C 0.3838(3) 0.14294(17) 0.8848(3) 0.0356(5) Uani 1 1 d . . . H4 H 0.3953 0.1078 0.9831 0.043 Uiso 1 1 calc R . . C5 C 0.3871(3) 0.08212(18) 0.7500(3) 0.0418(5) Uani 1 1 d . . . H5 H 0.4035 0.0054 0.7574 0.050 Uiso 1 1 calc R . . C6 C 0.3671(3) 0.13034(18) 0.6042(3) 0.0392(5) Uani 1 1 d . . . H6 H 0.3679 0.0873 0.5128 0.047 Uiso 1 1 calc R . . C7 C 0.3459(2) 0.24189(17) 0.5950(2) 0.0305(4) Uani 1 1 d . . . H7 H 0.3305 0.2760 0.4961 0.037 Uiso 1 1 calc R . . C8 C 0.3469(2) 0.30515(15) 0.7285(2) 0.0240(4) Uani 1 1 d . . . S9 S 0.33806(5) 0.44855(4) 0.70641(5) 0.02293(10) Uani 1 1 d . . . O10 O 0.49635(18) 0.49628(11) 0.79579(17) 0.0326(3) Uani 1 1 d . . . O11 O 0.32031(19) 0.47010(11) 0.54152(15) 0.0341(3) Uani 1 1 d . . . C12 C 0.1215(2) 0.48984(15) 0.7875(2) 0.0227(3) Uani 1 1 d . . . H12 H 0.1156 0.4529 0.8902 0.027 Uiso 1 1 calc R . . C13 C -0.0475(2) 0.4512(2) 0.6812(2) 0.0300(4) Uani 1 1 d . . . H13A H -0.1646 0.4649 0.7314 0.045 Uiso 1 1 calc R . . H13B H -0.0354 0.3730 0.6613 0.045 Uiso 1 1 calc R . . H13C H -0.0508 0.4910 0.5826 0.045 Uiso 1 1 calc R . . C14 C 0.1253(2) 0.61128(14) 0.8149(2) 0.0234(4) Uani 1 1 d . . . C15 C 0.1176(3) 0.68550(16) 0.6927(2) 0.0316(4) Uani 1 1 d . . . H15 H 0.1118 0.6592 0.5890 0.038 Uiso 1 1 calc R . . C16 C 0.1182(3) 0.79751(17) 0.7194(3) 0.0389(5) Uani 1 1 d . . . H16 H 0.1121 0.8471 0.6347 0.047 Uiso 1 1 calc R . . C17 C 0.1278(3) 0.83559(17) 0.8692(3) 0.0372(5) Uani 1 1 d . . . H17 H 0.1283 0.9119 0.8879 0.045 Uiso 1 1 calc R . . C18 C 0.1367(3) 0.76370(17) 0.9939(2) 0.0313(4) Uani 1 1 d . . . H18 H 0.1445 0.7909 1.0972 0.038 Uiso 1 1 calc R . . C19 C 0.1343(2) 0.65219(15) 0.9672(2) 0.0246(4) Uani 1 1 d . . . O20 O 0.13982(19) 0.57605(11) 1.08277(14) 0.0305(3) Uani 1 1 d . . . C21 C 0.1323(3) 0.61406(18) 1.2388(2) 0.0342(5) Uani 1 1 d . . . H21A H 0.1349 0.5516 1.3097 0.051 Uiso 1 1 calc R . . H21B H 0.0156 0.6555 1.2477 0.051 Uiso 1 1 calc R . . H21C H 0.2415 0.6611 1.2660 0.051 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 C1 0.0390(11) 0.0556(15) 0.0278(10) 0.0139(10) -0.0003(8) 0.0001(10) O2 0.0373(7) 0.0349(8) 0.0235(7) 0.0042(5) 0.0005(5) 0.0042(6) C3 0.0201(8) 0.0284(10) 0.0312(10) 0.0018(7) 0.0013(7) 0.0013(6) C4 0.0270(9) 0.0299(11) 0.0498(13) 0.0119(9) 0.0019(8) 0.0029(8) C5 0.0265(9) 0.0231(10) 0.0759(17) -0.0049(11) 0.0044(10) 0.0023(8) C6 0.0288(9) 0.0343(12) 0.0548(13) -0.0167(10) 0.0050(9) 0.0028(8) C7 0.0265(9) 0.0334(11) 0.0317(10) -0.0085(8) 0.0037(7) 0.0001(8) C8 0.0217(8) 0.0215(9) 0.0289(9) -0.0021(7) 0.0029(7) 0.0014(6) S9 0.02381(18) 0.0210(2) 0.02446(19) 0.00134(18) 0.00516(13) -0.00069(17) O10 0.0247(6) 0.0280(7) 0.0450(8) -0.0058(6) 0.0019(5) -0.0046(5) O11 0.0423(7) 0.0375(10) 0.0239(6) 0.0090(6) 0.0107(5) 0.0044(6) C12 0.0241(8) 0.0225(8) 0.0221(8) 0.0014(6) 0.0048(6) 0.0008(6) C13 0.0259(7) 0.0306(9) 0.0331(9) 0.0023(10) -0.0012(6) -0.0023(9) C14 0.0227(8) 0.0218(9) 0.0258(9) 0.0024(6) 0.0022(6) 0.0015(6) C15 0.0415(10) 0.0263(10) 0.0270(9) 0.0037(7) 0.0032(8) 0.0021(8) C16 0.0498(12) 0.0262(11) 0.0411(12) 0.0108(9) 0.0077(9) 0.0040(9) C17 0.0444(11) 0.0214(10) 0.0468(13) -0.0004(8) 0.0102(9) 0.0014(8) C18 0.0320(10) 0.0279(10) 0.0342(10) -0.0053(8) 0.0044(8) 0.0000(8) C19 0.0231(8) 0.0249(9) 0.0260(9) 0.0008(7) 0.0030(6) 0.0024(7) O20 0.0414(7) 0.0309(8) 0.0196(6) 0.0020(5) 0.0039(5) 0.0029(6) C21 0.0347(10) 0.0489(14) 0.0190(9) -0.0018(8) 0.0012(7) 0.0048(9) _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 C1 O2 1.434(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C3 1.351(2) . ? C3 C4 1.398(3) . ? C3 C8 1.404(3) . ? C4 C5 1.385(3) . ? C4 H4 0.9500 . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 C7 1.378(3) . ? C6 H6 0.9500 . ? C7 C8 1.389(2) . ? C7 H7 0.9500 . ? C8 S9 1.770(2) . ? S9 O10 1.4391(13) . ? S9 O11 1.4447(13) . ? S9 C12 1.8078(18) . ? C12 C14 1.508(3) . ? C12 C13 1.530(2) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.392(3) . ? C14 C19 1.405(2) . ? C15 C16 1.393(3) . ? C15 H15 0.9500 . ? C16 C17 1.373(3) . ? C16 H16 0.9500 . ? C17 C18 1.390(3) . ? C17 H17 0.9500 . ? C18 C19 1.387(3) . ? C18 H18 0.9500 . ? C19 O20 1.365(2) . ? O20 C21 1.431(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O2 C1 117.69(17) . . ? O2 C3 C4 124.88(18) . . ? O2 C3 C8 116.62(17) . . ? C4 C3 C8 118.51(18) . . ? C5 C4 C3 119.8(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 118.6(2) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C6 C7 C8 120.9(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C7 C8 C3 120.51(19) . . ? C7 C8 S9 117.88(15) . . ? C3 C8 S9 121.54(14) . . ? O10 S9 O11 117.49(9) . . ? O10 S9 C8 109.06(8) . . ? O11 S9 C8 106.73(8) . . ? O10 S9 C12 109.28(8) . . ? O11 S9 C12 108.43(8) . . ? C8 S9 C12 105.14(8) . . ? C14 C12 C13 113.84(15) . . ? C14 C12 S9 109.37(12) . . ? C13 C12 S9 109.37(12) . . ? C14 C12 H12 108.0 . . ? C13 C12 H12 108.0 . . ? S9 C12 H12 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 118.21(17) . . ? C15 C14 C12 121.86(16) . . ? C19 C14 C12 119.92(16) . . ? C14 C15 C16 121.36(19) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 119.4(2) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.7(2) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 119.84(19) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? O20 C19 C18 123.62(17) . . ? O20 C19 C14 115.91(16) . . ? C18 C19 C14 120.47(17) . . ? C19 O20 C21 117.69(16) . . ? O20 C21 H21A 109.5 . . ? O20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C1 O2 C3 C4 -2.5(3) . . . . ? C1 O2 C3 C8 177.63(15) . . . . ? O2 C3 C4 C5 -179.83(17) . . . . ? C8 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C4 C5 C6 C7 0.9(3) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C6 C7 C8 C3 -2.0(3) . . . . ? C6 C7 C8 S9 175.02(14) . . . . ? O2 C3 C8 C7 -178.54(15) . . . . ? C4 C3 C8 C7 1.6(3) . . . . ? O2 C3 C8 S9 4.5(2) . . . . ? C4 C3 C8 S9 -175.32(13) . . . . ? C7 C8 S9 O10 -124.66(14) . . . . ? C3 C8 S9 O10 52.35(16) . . . . ? C7 C8 S9 O11 3.20(16) . . . . ? C3 C8 S9 O11 -179.79(13) . . . . ? C7 C8 S9 C12 118.25(14) . . . . ? C3 C8 S9 C12 -64.74(16) . . . . ? O10 S9 C12 C14 47.66(14) . . . . ? O11 S9 C12 C14 -81.54(13) . . . . ? C8 S9 C12 C14 164.59(11) . . . . ? O10 S9 C12 C13 172.95(13) . . . . ? O11 S9 C12 C13 43.76(15) . . . . ? C8 S9 C12 C13 -70.11(14) . . . . ? C13 C12 C14 C15 -54.6(2) . . . . ? S9 C12 C14 C15 68.10(19) . . . . ? C13 C12 C14 C19 124.56(17) . . . . ? S9 C12 C14 C19 -112.77(15) . . . . ? C19 C14 C15 C16 -0.2(3) . . . . ? C12 C14 C15 C16 178.97(17) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C16 C17 C18 C19 -0.6(3) . . . . ? C17 C18 C19 O20 -179.02(17) . . . . ? C17 C18 C19 C14 0.8(3) . . . . ? C15 C14 C19 O20 179.41(16) . . . . ? C12 C14 C19 O20 0.3(2) . . . . ? C15 C14 C19 C18 -0.5(3) . . . . ? C12 C14 C19 C18 -179.61(15) . . . . ? C18 C19 O20 C21 5.2(2) . . . . ? C14 C19 O20 C21 -174.65(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.394 _refine_diff_density_min -0.624 _refine_diff_density_rms 0.147 #===END============================================================== data_compound_17 _database_code_depnum_ccdc_archive 'CCDC 759287' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C15 H16 O3 S' _chemical_formula_sum 'C15 H16 O3 S' _chemical_formula_iupac ? _chemical_formula_weight 276.34 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 c 1' _symmetry_space_group_name_Hall ' P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 15.4234(11) _cell_length_b 5.4410(4) _cell_length_c 8.1642(5) _cell_angle_alpha 90 _cell_angle_beta 105.124(2) _cell_angle_gamma 90 _cell_volume 661.40(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3560 _cell_measurement_theta_min 2.7360 _cell_measurement_theta_max 27.0188 _cell_measurement_temperature 180.(2) _exptl_crystal_description Block _exptl_crystal_colour 'clear colourless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs Version 2008/1' _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.95 _exptl_special_details ; ; _diffrn_ambient_temperature 180.(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX DUO' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 5584 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 27.09 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _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. ; _reflns_number_total 2873 _reflns_number_gt 2753 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_gt 0.0904 _refine_ls_wR_factor_ref 0.0922 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_number_reflns 2873 _refine_ls_number_parameters 174 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.1685P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.462 _refine_diff_density_min -0.211 _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 0.06(7) _chemical_absolute_configuration ad 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' 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' _computing_data_collection 'Bruker Instrument Service v2009, 7, 0, 0' _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL--97; PLATON' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.60484(4) 0.83321(9) 0.24811(6) 0.02521(12) Uani d . 1 . . O O1 0.23595(10) 0.6981(2) 0.3221(2) 0.0299(4) Uani d . 1 . . O O2 1.03399(10) 0.7964(2) 0.4305(2) 0.0321(4) Uani d . 1 . . O O3 0.62365(11) 1.1000(2) 0.2796(2) 0.0390(4) Uani d . 1 . . C C1 0.18317(14) 0.4920(5) 0.2499(2) 0.0361(5) Uani d . 1 . . H H1A 0.1769 0.4883 0.1274 0.054 Uiso calc R 1 . . H H1B 0.1236 0.5048 0.271 0.054 Uiso calc R 1 . . H H1C 0.2126 0.3408 0.3016 0.054 Uiso calc R 1 . . C C2 0.32128(12) 0.7132(4) 0.3025(2) 0.0225(4) Uani d . 1 . . C C3 0.35943(13) 0.5424(4) 0.2151(2) 0.0254(4) Uani d . 1 . . H H3 0.3259 0.4027 0.1649 0.03 Uiso calc R 1 . . C C4 0.44628(13) 0.5761(4) 0.2016(2) 0.0263(4) Uani d . 1 . . H H4 0.4724 0.46 0.1419 0.032 Uiso calc R 1 . . C C5 0.49490(12) 0.7802(4) 0.2756(2) 0.0214(4) Uani d . 1 . . C C6 0.66952(12) 0.6694(4) 0.4361(2) 0.0230(4) Uani d . 1 . . H H6A 0.6563 0.7367 0.5396 0.028 Uiso calc R 1 . . H H6B 0.654 0.4925 0.4278 0.028 Uiso calc R 1 . . C C7 0.76759(12) 0.7047(4) 0.4433(2) 0.0209(4) Uani d . 1 . . C C8 0.81585(12) 0.9047(4) 0.5261(2) 0.0234(4) Uani d . 1 . . H H8 0.7873 1.018 0.5836 0.028 Uiso calc R 1 . . C C9 0.90520(13) 0.9424(4) 0.5264(2) 0.0250(4) Uani d . 1 . . H H9 0.9375 1.0791 0.5842 0.03 Uiso calc R 1 . . C C10 0.94643(12) 0.7771(4) 0.4409(2) 0.0227(4) Uani d . 1 . . C C11 1.08298(14) 1.0079(5) 0.5079(2) 0.0352(5) Uani d . 1 . . H H11A 1.0539 1.1567 0.4516 0.053 Uiso calc R 1 . . H H11B 1.1446 0.9991 0.4968 0.053 Uiso calc R 1 . . H H11C 1.084 1.0128 0.6283 0.053 Uiso calc R 1 . . C C12 0.81081(13) 0.5403(4) 0.3604(2) 0.0239(4) Uani d . 1 . . H H12 0.779 0.4013 0.3048 0.029 Uiso calc R 1 . . C C13 0.89897(13) 0.5755(4) 0.3574(2) 0.0264(4) Uani d . 1 . . H H13 0.9272 0.463 0.2987 0.032 Uiso calc R 1 . . C C14 0.45671(13) 0.9523(4) 0.3607(2) 0.0243(4) Uani d . 1 . . H H14 0.4899 1.0937 0.4088 0.029 Uiso calc R 1 . . C C15 0.37028(13) 0.9178(4) 0.3757(2) 0.0251(4) Uani d . 1 . . H H15 0.3444 1.034 0.4359 0.03 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0230(2) 0.0280(2) 0.0251(2) -0.0015(2) 0.00697(17) 0.0049(2) O1 0.0215(7) 0.0325(9) 0.0363(9) -0.0004(5) 0.0087(5) -0.0025(7) O2 0.0219(7) 0.0370(10) 0.0381(9) -0.0006(5) 0.0089(5) -0.0040(7) O3 0.0369(10) 0.0298(9) 0.0506(11) -0.0052(7) 0.0122(8) 0.0082(8) C1 0.0244(10) 0.0395(14) 0.0440(13) -0.0058(10) 0.0086(9) -0.0005(11) C2 0.0208(9) 0.0250(11) 0.0212(10) 0.0011(7) 0.0045(8) 0.0038(8) C3 0.0254(10) 0.0206(11) 0.0288(11) -0.0025(8) 0.0046(8) -0.0017(9) C4 0.0286(11) 0.0242(11) 0.0275(10) 0.0001(9) 0.0100(9) -0.0054(9) C5 0.0196(9) 0.0230(11) 0.0210(10) 0.0011(8) 0.0044(7) 0.0052(8) C6 0.0241(9) 0.0237(11) 0.0210(9) 0.0044(8) 0.0054(7) 0.0032(8) C7 0.0238(9) 0.0191(11) 0.0202(9) -0.0001(7) 0.0062(7) 0.0032(8) C8 0.0267(10) 0.0207(10) 0.0243(10) 0.0028(8) 0.0096(8) -0.0021(8) C9 0.0272(10) 0.0216(11) 0.0258(10) -0.0037(8) 0.0061(8) -0.0032(8) C10 0.0213(9) 0.0254(11) 0.0215(10) 0.0030(8) 0.0057(8) 0.0042(8) C11 0.0251(10) 0.0347(13) 0.0451(14) -0.0074(10) 0.0084(10) -0.0021(11) C12 0.0276(10) 0.0197(10) 0.0235(10) 0.0007(8) 0.0049(8) -0.0034(8) C13 0.0292(11) 0.0232(11) 0.0279(10) 0.0056(8) 0.0094(9) -0.0034(9) C14 0.0249(10) 0.0226(11) 0.0234(10) -0.0020(8) 0.0024(8) -0.0008(8) C15 0.0269(10) 0.0219(11) 0.0264(10) 0.0041(8) 0.0068(8) -0.0018(9) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O3 . 1.4896(18) ? S1 C5 . 1.791(2) ? S1 C6 . 1.829(2) ? O1 C2 . 1.369(2) ? O1 C1 . 1.420(3) ? O2 C10 . 1.379(2) ? O2 C11 . 1.430(3) ? C1 H1A . 0.98 ? C1 H1B . 0.98 ? C1 H1C . 0.98 ? C2 C15 . 1.390(3) ? C2 C3 . 1.392(3) ? C3 C4 . 1.385(3) ? C3 H3 . 0.95 ? C4 C5 . 1.387(3) ? C4 H4 . 0.95 ? C5 C14 . 1.386(3) ? C6 C7 . 1.511(3) ? C6 H6A . 0.99 ? C6 H6B . 0.99 ? C7 C8 . 1.390(3) ? C7 C12 . 1.392(3) ? C8 C9 . 1.393(3) ? C8 H8 . 0.95 ? C9 C10 . 1.390(3) ? C9 H9 . 0.95 ? C10 C13 . 1.394(3) ? C11 H11A . 0.98 ? C11 H11B . 0.98 ? C11 H11C . 0.98 ? C12 C13 . 1.380(3) ? C12 H12 . 0.95 ? C13 H13 . 0.95 ? C14 C15 . 1.383(3) ? C14 H14 . 0.95 ? C15 H15 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 S1 C5 . . 106.47(10) ? O3 S1 C6 . . 106.92(10) ? C5 S1 C6 . . 98.23(9) ? C2 O1 C1 . . 117.60(17) ? C10 O2 C11 . . 116.57(17) ? O1 C1 H1A . . 109.5 ? O1 C1 H1B . . 109.5 ? H1A C1 H1B . . 109.5 ? O1 C1 H1C . . 109.5 ? H1A C1 H1C . . 109.5 ? H1B C1 H1C . . 109.5 ? O1 C2 C15 . . 115.42(18) ? O1 C2 C3 . . 124.6(2) ? C15 C2 C3 . . 120.00(18) ? C4 C3 C2 . . 120.0(2) ? C4 C3 H3 . . 120.0 ? C2 C3 H3 . . 120.0 ? C3 C4 C5 . . 119.7(2) ? C3 C4 H4 . . 120.1 ? C5 C4 H4 . . 120.1 ? C14 C5 C4 . . 120.48(18) ? C14 C5 S1 . . 119.61(16) ? C4 C5 S1 . . 119.76(15) ? C7 C6 S1 . . 107.00(13) ? C7 C6 H6A . . 110.3 ? S1 C6 H6A . . 110.3 ? C7 C6 H6B . . 110.3 ? S1 C6 H6B . . 110.3 ? H6A C6 H6B . . 108.6 ? C8 C7 C12 . . 118.41(18) ? C8 C7 C6 . . 121.47(17) ? C12 C7 C6 . . 120.1(2) ? C7 C8 C9 . . 121.33(18) ? C7 C8 H8 . . 119.3 ? C9 C8 H8 . . 119.3 ? C10 C9 C8 . . 119.1(2) ? C10 C9 H9 . . 120.5 ? C8 C9 H9 . . 120.5 ? O2 C10 C9 . . 124.4(2) ? O2 C10 C13 . . 115.33(18) ? C9 C10 C13 . . 120.26(18) ? O2 C11 H11A . . 109.5 ? O2 C11 H11B . . 109.5 ? H11A C11 H11B . . 109.5 ? O2 C11 H11C . . 109.5 ? H11A C11 H11C . . 109.5 ? H11B C11 H11C . . 109.5 ? C13 C12 C7 . . 121.2(2) ? C13 C12 H12 . . 119.4 ? C7 C12 H12 . . 119.4 ? C12 C13 C10 . . 119.7(2) ? C12 C13 H13 . . 120.2 ? C10 C13 H13 . . 120.2 ? C15 C14 C5 . . 119.9(2) ? C15 C14 H14 . . 120.1 ? C5 C14 H14 . . 120.1 ? C14 C15 C2 . . 120.0(2) ? C14 C15 H15 . . 120.0 ? C2 C15 H15 . . 120.0 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C1 O1 C2 C15 . . . . -179.9(2) ? C1 O1 C2 C3 . . . . 0.8(3) ? O1 C2 C3 C4 . . . . 179.5(2) ? C15 C2 C3 C4 . . . . 0.2(3) ? C2 C3 C4 C5 . . . . 0.1(3) ? C3 C4 C5 C14 . . . . -1.0(3) ? C3 C4 C5 S1 . . . . -176.49(16) ? O3 S1 C5 C14 . . . . -17.3(2) ? C6 S1 C5 C14 . . . . 93.19(18) ? O3 S1 C5 C4 . . . . 158.27(17) ? C6 S1 C5 C4 . . . . -91.28(18) ? O3 S1 C6 C7 . . . . -66.59(16) ? C5 S1 C6 C7 . . . . -176.68(15) ? S1 C6 C7 C8 . . . . 88.6(2) ? S1 C6 C7 C12 . . . . -88.9(2) ? C12 C7 C8 C9 . . . . 0.3(3) ? C6 C7 C8 C9 . . . . -177.22(18) ? C7 C8 C9 C10 . . . . 0.5(3) ? C11 O2 C10 C9 . . . . -2.7(3) ? C11 O2 C10 C13 . . . . 177.0(2) ? C8 C9 C10 O2 . . . . 179.2(2) ? C8 C9 C10 C13 . . . . -0.6(3) ? C8 C7 C12 C13 . . . . -1.0(3) ? C6 C7 C12 C13 . . . . 176.5(2) ? C7 C12 C13 C10 . . . . 1.0(3) ? O2 C10 C13 C12 . . . . -180.0(2) ? C9 C10 C13 C12 . . . . -0.2(3) ? C4 C5 C14 C15 . . . . 1.5(3) ? S1 C5 C14 C15 . . . . 177.05(15) ? C5 C14 C15 C2 . . . . -1.2(3) ? O1 C2 C15 C14 . . . . -178.99(18) ? C3 C2 C15 C14 . . . . 0.4(3) ? #===END============================================================== data_compound_18 _database_code_depnum_ccdc_archive 'CCDC 759288' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method 'APEX2 v2009.7-0' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C13 H10 F2 O S' _chemical_formula_sum 'C13 H10 F2 O S' _chemical_formula_iupac ? _chemical_formula_weight 252.27 _chemical_melting_point ? _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall ' P 2c -2ac' 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 8.1909(9) _cell_length_b 5.4433(5) _cell_length_c 24.948(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1112.3(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4402 _cell_measurement_theta_min 3.7432 _cell_measurement_theta_max 28.2281 _cell_measurement_temperature 100.(2) _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs Version 2008/1' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.96 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX DUO' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 7201 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 28.40 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _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. ; _reflns_number_total 2747 _reflns_number_gt 2661 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_gt 0.0818 _refine_ls_wR_factor_ref 0.0827 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_number_reflns 2747 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.3400P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.604 _refine_diff_density_min -0.223 _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 0.03(6) _chemical_absolute_configuration ad 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' F F 0.0171 0.0103 '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' _computing_data_collection 'Bruker Instrument Service v2009, 7, 0, 0' _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL--97; PLATON' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.79642(5) 0.32977(6) 0.262614(17) 0.01542(10) Uani d . 1 . . O O2 0.81942(17) 0.5991(2) 0.25217(5) 0.0221(2) Uani d . 1 . . C C3 0.9522(2) 0.1681(2) 0.22363(6) 0.0139(2) Uani d . 1 . . H H3A 1.0618 0.2355 0.2317 0.017 Uiso calc R 1 . . H H3B 0.9518 -0.009 0.2326 0.017 Uiso calc R 1 . . C C4 0.9121(2) 0.2045(2) 0.16502(6) 0.0128(2) Uani d . 1 . . C C5 0.9721(2) 0.4078(2) 0.13723(6) 0.0154(2) Uani d . 1 . . H H5 1.0427 0.5202 0.1549 0.019 Uiso calc R 1 . . C C6 0.9296(2) 0.4476(2) 0.08380(6) 0.0171(2) Uani d . 1 . . H H6 0.9706 0.5852 0.0646 0.02 Uiso calc R 1 . . C C7 0.8261(2) 0.2808(2) 0.05969(6) 0.0163(2) Uani d . 1 . . C C8 0.7641(2) 0.0757(2) 0.08543(6) 0.0174(2) Uani d . 1 . . H H8 0.6937 -0.036 0.0675 0.021 Uiso calc R 1 . . C C9 0.8092(2) 0.0396(2) 0.13866(6) 0.0149(2) Uani d . 1 . . H H9 0.7691 -0.0999 0.1574 0.018 Uiso calc R 1 . . F F10 0.78144(14) 0.3219(2) 0.00775(5) 0.0254(2) Uani d . 1 . . C C11 0.8798(2) 0.2715(2) 0.32765(6) 0.0136(2) Uani d . 1 . . C C12 0.9820(2) 0.4448(2) 0.35097(6) 0.0158(2) Uani d . 1 . . H H12 1.0108 0.5893 0.3318 0.019 Uiso calc R 1 . . C C13 1.0424(2) 0.4062(2) 0.40269(6) 0.0180(2) Uani d . 1 . . H H13 1.1133 0.5216 0.4192 0.022 Uiso calc R 1 . . C C14 0.9952(2) 0.1935(2) 0.42894(6) 0.0170(2) Uani d . 1 . . C C15 0.8910(2) 0.0208(2) 0.40676(6) 0.0183(2) Uani d . 1 . . H H15 0.8601 -0.1215 0.4263 0.022 Uiso calc R 1 . . C C16 0.8328(2) 0.0609(2) 0.35527(6) 0.0168(2) Uani d . 1 . . H H16 0.7615 -0.0546 0.339 0.02 Uiso calc R 1 . . F F17 1.05294(16) 0.1528(2) 0.47909(4) 0.0243(2) Uani d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0158(2) 0.01847(17) 0.01195(17) 0.00354(13) -0.00085(17) -0.00040(16) O2 0.0317(7) 0.0174(5) 0.0172(7) 0.0046(5) -0.0018(5) 0.0031(5) C3 0.0154(8) 0.0149(5) 0.0114(7) 0.0019(5) 0.0018(5) -0.0013(5) C4 0.0127(8) 0.0133(5) 0.0125(7) 0.0025(5) 0.0009(5) -0.0003(5) C5 0.0146(8) 0.0161(7) 0.0156(7) -0.0025(5) -0.0012(7) -0.0008(5) C6 0.0184(9) 0.0178(7) 0.0150(8) -0.0007(7) 0.0005(5) 0.0036(5) C7 0.0158(8) 0.0238(8) 0.0092(7) 0.0023(7) -0.0002(5) -0.0008(5) C8 0.0171(9) 0.0200(7) 0.0153(7) -0.0042(7) -0.0004(5) -0.0033(5) C9 0.0156(8) 0.0160(7) 0.0129(7) -0.0009(5) 0.0018(5) 0.0007(5) F10 0.0314(9) 0.0329(5) 0.0117(5) -0.0037(5) -0.0054(5) 0.0032(4) C11 0.0143(8) 0.0166(7) 0.0098(5) 0.0029(5) 0.0012(5) -0.0016(5) C12 0.0153(8) 0.0152(7) 0.0170(8) 0.0008(5) 0.0026(5) -0.0008(5) C13 0.0185(9) 0.0192(8) 0.0164(7) -0.0007(7) -0.0006(7) -0.0049(5) C14 0.0195(9) 0.0232(8) 0.0084(7) 0.0067(7) -0.0006(5) 0.0001(5) C15 0.0220(9) 0.0169(7) 0.0159(8) 0.0012(7) 0.0028(7) 0.0020(5) C16 0.0169(8) 0.0161(7) 0.0174(8) -0.0010(7) 0.0014(7) -0.0013(5) F17 0.0303(7) 0.0317(5) 0.0109(5) 0.0065(5) -0.0057(4) -0.0003(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O2 . 1.5010(13) ? S1 C11 . 1.7886(17) ? S1 C3 . 1.8300(17) ? C3 C4 . 1.512(2) ? C4 C5 . 1.395(2) ? C4 C9 . 1.396(2) ? C5 C6 . 1.395(2) ? C6 C7 . 1.380(2) ? C7 F10 . 1.365(2) ? C7 C8 . 1.384(2) ? C8 C9 . 1.392(2) ? C11 C12 . 1.389(2) ? C11 C16 . 1.391(2) ? C12 C13 . 1.398(3) ? C13 C14 . 1.385(2) ? C14 F17 . 1.3556(18) ? C14 C15 . 1.385(3) ? C15 C16 . 1.387(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 S1 C11 . . 106.43(8) ? O2 S1 C3 . . 106.85(8) ? C11 S1 C3 . . 97.51(8) ? C4 C3 S1 . . 107.43(11) ? C5 C4 C9 . . 119.26(15) ? C5 C4 C3 . . 120.52(15) ? C9 C4 C3 . . 120.18(14) ? C6 C5 C4 . . 120.68(15) ? C7 C6 C5 . . 117.88(15) ? F10 C7 C6 . . 118.07(15) ? F10 C7 C8 . . 118.31(15) ? C6 C7 C8 . . 123.61(16) ? C7 C8 C9 . . 117.33(16) ? C8 C9 C4 . . 121.24(15) ? C12 C11 C16 . . 121.22(15) ? C12 C11 S1 . . 119.31(12) ? C16 C11 S1 . . 119.34(13) ? C11 C12 C13 . . 119.86(15) ? C14 C13 C12 . . 117.61(16) ? F17 C14 C13 . . 118.41(16) ? F17 C14 C15 . . 118.19(15) ? C13 C14 C15 . . 123.39(15) ? C14 C15 C16 . . 118.33(16) ? C15 C16 C11 . . 119.57(16) ? #===END============================================================== data_compound_19 _database_code_depnum_ccdc_archive 'CCDC 759289' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 Br O S' _chemical_formula_sum 'C13 H11 Br O S' _chemical_formula_weight 295.19 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 8.2638(2) _cell_length_b 5.42770(10) _cell_length_c 27.4202(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1229.89(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11103 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 3.487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.677 _exptl_absorpt_correction_T_max 0.842 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The 0 0 -4 and 0 1 0 reflections have been omitted due to the beamstop. absolute configuration test conclusive. correct enantiomer R1=0.0539, wR2=0.1312 incorrect enantiomer R1=0.0826, wR2=0.2066 refining in SHELXL-97 using TWIN,BASF refined to 0.00001 for the correct enantiomer. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6583 _diffrn_reflns_av_R_equivalents 0.0694 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1873 _reflns_number_gt 1563 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL--97; PLATON' _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^)+(0.0595P)^2^+0.8294P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.019(18) _chemical_absolute_configuration ad _refine_ls_number_reflns 1873 _refine_ls_number_parameters 145 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.189 _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 Br1 Br 0.81035(11) 0.79275(16) -0.00339(3) 0.0898(4) Uani 1 1 d . . . S1 S 0.81796(16) 0.8266(2) 0.24817(6) 0.0396(4) Uani 1 1 d . . . O3 O 0.8402(5) 1.0933(7) 0.23706(17) 0.0507(11) Uani 1 1 d . . . C4 C 0.8042(8) 0.5522(13) 0.0882(3) 0.0536(17) Uani 1 1 d . . . H4A H 0.7362 0.4367 0.0721 0.064 Uiso 1 1 calc R . . C5 C 0.9616(8) 0.9249(14) 0.0859(3) 0.0528(17) Uani 1 1 d . . . H5A H 1.0015 1.0621 0.0681 0.063 Uiso 1 1 calc R . . C6 C 0.9392(7) 0.6941(11) 0.1611(2) 0.0376(13) Uani 1 1 d . . . C7 C 0.8440(7) 0.5235(11) 0.1371(2) 0.0458(15) Uani 1 1 d . . . H7A H 0.8049 0.3840 0.1544 0.055 Uiso 1 1 calc R . . C8 C 0.8479(8) 0.5769(12) 0.3346(2) 0.0472(15) Uani 1 1 d . . . H8A H 0.7753 0.4602 0.3209 0.057 Uiso 1 1 calc R . . C9 C 0.9991(8) 0.8959(12) 0.1350(2) 0.0484(15) Uani 1 1 d . . . H9A H 1.0658 1.0137 0.1509 0.058 Uiso 1 1 calc R . . C10 C 0.9988(8) 0.9530(11) 0.3285(2) 0.0452(14) Uani 1 1 d . . . H10A H 1.0301 1.0926 0.3098 0.054 Uiso 1 1 calc R . . C11 C 0.9071(9) 0.5474(13) 0.3820(3) 0.0541(17) Uani 1 1 d . . . H11A H 0.8786 0.4048 0.4001 0.065 Uiso 1 1 calc R . . C12 C 0.8972(7) 0.7786(10) 0.3085(2) 0.0387(13) Uani 1 1 d . . . C13 C 1.0051(8) 0.7200(11) 0.4023(2) 0.0526(16) Uani 1 1 d . . . H13A H 1.0401 0.7013 0.4351 0.063 Uiso 1 1 calc R . . C14 C 0.9759(7) 0.6664(10) 0.2142(2) 0.0392(13) Uani 1 1 d . . . H14A H 1.0831 0.7386 0.2218 0.047 Uiso 1 1 calc R . . H14B H 0.9778 0.4898 0.2233 0.047 Uiso 1 1 calc R . . C15 C 1.0547(9) 0.9251(13) 0.3753(2) 0.0522(17) Uani 1 1 d . . . H15A H 1.1261 1.0432 0.3892 0.063 Uiso 1 1 calc R . . C51 C 0.8659(9) 0.7518(13) 0.0638(3) 0.0530(16) 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 Br1 0.1211(9) 0.1220(8) 0.0264(4) 0.0069(6) -0.0071(6) 0.0035(5) S1 0.0393(7) 0.0460(7) 0.0335(8) -0.0001(7) -0.0010(7) 0.0037(6) O3 0.062(2) 0.049(2) 0.040(3) 0.006(2) 0.001(2) 0.009(2) C4 0.060(4) 0.059(4) 0.041(4) -0.007(3) -0.007(3) -0.006(3) C5 0.060(4) 0.061(4) 0.038(4) 0.006(3) 0.009(3) 0.002(3) C6 0.036(3) 0.041(3) 0.036(3) -0.003(3) 0.006(3) 0.004(3) C7 0.059(4) 0.043(3) 0.036(4) 0.003(3) 0.001(3) -0.007(3) C8 0.057(4) 0.049(3) 0.036(4) 0.000(3) 0.002(3) 0.004(3) C9 0.053(4) 0.050(3) 0.042(4) 0.002(3) 0.003(3) -0.007(3) C10 0.051(3) 0.049(3) 0.036(3) 0.000(3) 0.004(3) 0.000(3) C11 0.068(5) 0.051(4) 0.042(4) 0.013(3) 0.010(4) 0.007(4) C12 0.036(3) 0.042(3) 0.038(4) 0.001(3) 0.002(3) 0.003(3) C13 0.063(4) 0.064(4) 0.031(4) -0.001(3) 0.002(3) 0.006(3) C14 0.045(3) 0.040(3) 0.033(3) -0.001(2) -0.001(3) 0.002(3) C15 0.065(5) 0.058(4) 0.034(4) -0.004(3) -0.001(3) -0.005(3) C51 0.059(4) 0.068(4) 0.032(4) 0.003(3) -0.004(3) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C51 1.911(7) . ? S1 O3 1.491(4) . ? S1 C12 1.798(7) . ? S1 C14 1.824(6) . ? C4 C51 1.372(10) . ? C4 C7 1.390(9) . ? C4 H4A 0.9500 . ? C5 C51 1.370(10) . ? C5 C9 1.389(9) . ? C5 H5A 0.9500 . ? C6 C7 1.382(9) . ? C6 C9 1.399(9) . ? C6 C14 1.496(8) . ? C7 H7A 0.9500 . ? C8 C12 1.371(9) . ? C8 C11 1.396(10) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C15 1.374(9) . ? C10 C12 1.379(9) . ? C10 H10A 0.9500 . ? C11 C13 1.358(10) . ? C11 H11A 0.9500 . ? C13 C15 1.399(9) . ? C13 H13A 0.9500 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 C12 106.5(3) . . ? O3 S1 C14 105.7(3) . . ? C12 S1 C14 98.0(3) . . ? C51 C4 C7 118.1(6) . . ? C51 C4 H4A 120.9 . . ? C7 C4 H4A 120.9 . . ? C51 C5 C9 118.7(7) . . ? C51 C5 H5A 120.6 . . ? C9 C5 H5A 120.6 . . ? C7 C6 C9 118.9(6) . . ? C7 C6 C14 120.8(6) . . ? C9 C6 C14 120.3(5) . . ? C6 C7 C4 121.3(6) . . ? C6 C7 H7A 119.4 . . ? C4 C7 H7A 119.4 . . ? C12 C8 C11 118.3(6) . . ? C12 C8 H8A 120.9 . . ? C11 C8 H8A 120.9 . . ? C5 C9 C6 120.3(6) . . ? C5 C9 H9A 119.8 . . ? C6 C9 H9A 119.8 . . ? C15 C10 C12 120.0(6) . . ? C15 C10 H10A 120.0 . . ? C12 C10 H10A 120.0 . . ? C13 C11 C8 120.8(6) . . ? C13 C11 H11A 119.6 . . ? C8 C11 H11A 119.6 . . ? C8 C12 C10 121.4(6) . . ? C8 C12 S1 119.3(5) . . ? C10 C12 S1 119.2(4) . . ? C11 C13 C15 120.4(7) . . ? C11 C13 H13A 119.8 . . ? C15 C13 H13A 119.8 . . ? C6 C14 S1 107.7(4) . . ? C6 C14 H14A 110.2 . . ? S1 C14 H14A 110.2 . . ? C6 C14 H14B 110.2 . . ? S1 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? C10 C15 C13 119.0(7) . . ? C10 C15 H15A 120.5 . . ? C13 C15 H15A 120.5 . . ? C5 C51 C4 122.7(7) . . ? C5 C51 Br1 119.1(5) . . ? C4 C51 Br1 118.2(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 C9 C6 C7 C4 -1.5(9) . . . . ? C14 C6 C7 C4 177.6(6) . . . . ? C51 C4 C7 C6 1.8(10) . . . . ? C51 C5 C9 C6 -0.3(10) . . . . ? C7 C6 C9 C5 0.7(9) . . . . ? C14 C6 C9 C5 -178.4(6) . . . . ? C12 C8 C11 C13 3.0(10) . . . . ? C11 C8 C12 C10 -1.9(9) . . . . ? C11 C8 C12 S1 -178.1(5) . . . . ? C15 C10 C12 C8 0.9(9) . . . . ? C15 C10 C12 S1 177.1(5) . . . . ? O3 S1 C12 C8 158.9(5) . . . . ? C14 S1 C12 C8 -92.0(5) . . . . ? O3 S1 C12 C10 -17.3(5) . . . . ? C14 S1 C12 C10 91.7(5) . . . . ? C8 C11 C13 C15 -3.1(10) . . . . ? C7 C6 C14 S1 -90.0(6) . . . . ? C9 C6 C14 S1 89.2(6) . . . . ? O3 S1 C14 C6 -67.3(4) . . . . ? C12 S1 C14 C6 -177.0(4) . . . . ? C12 C10 C15 C13 -0.9(10) . . . . ? C11 C13 C15 C10 2.1(10) . . . . ? C9 C5 C51 C4 0.7(11) . . . . ? C9 C5 C51 Br1 178.9(5) . . . . ? C7 C4 C51 C5 -1.4(11) . . . . ? C7 C4 C51 Br1 -179.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.862 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.104 #===END============================================================== data_compound_23 _database_code_depnum_ccdc_archive 'CCDC 759290' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 O S' _chemical_formula_sum 'C14 H14 O S' _chemical_formula_weight 230.31 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' 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.2961(6) _cell_length_b 5.75060(10) _cell_length_c 15.7264(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.1590(10) _cell_angle_gamma 90.00 _cell_volume 2369.99(8) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2936 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description Blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The 2 0 0 and -2 0 2 reflections have been omitted due to the beamstop. ; _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 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2712 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2712 _reflns_number_gt 2407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0449P)^2^+1.7817P] 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 2712 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.21027(5) 0.5203(2) 0.03792(9) 0.0227(3) Uani 1 1 d . . . H1 H 0.1924 0.4172 -0.0108 0.027 Uiso 1 1 calc R . . C2 C 0.25758(5) 0.4593(2) 0.10284(9) 0.0249(3) Uani 1 1 d . . . H2 H 0.2721 0.3128 0.0989 0.030 Uiso 1 1 calc R . . C3 C 0.28375(5) 0.6113(2) 0.17359(9) 0.0238(3) Uani 1 1 d . . . H3 H 0.3164 0.5697 0.2171 0.029 Uiso 1 1 calc R . . C4 C 0.26237(5) 0.8231(2) 0.18079(9) 0.0243(3) Uani 1 1 d . . . H4 H 0.2801 0.9255 0.2298 0.029 Uiso 1 1 calc R . . C5 C 0.21485(5) 0.8864(2) 0.11627(8) 0.0207(3) Uani 1 1 d . . . H5 H 0.2001 1.0318 0.1208 0.025 Uiso 1 1 calc R . . C6 C 0.18946(4) 0.7344(2) 0.04540(8) 0.0172(2) Uani 1 1 d . . . S7 S 0.131264(11) 0.82557(5) -0.043022(19) 0.01803(10) Uani 1 1 d . . . O8 O 0.12119(3) 1.06955(15) -0.02079(6) 0.0239(2) Uani 1 1 d . . . C9 C 0.08619(4) 0.6313(2) -0.01762(8) 0.0178(2) Uani 1 1 d . . . H9 H 0.0964 0.4670 -0.0227 0.021 Uiso 1 1 calc R . . C10 C 0.03416(5) 0.6731(3) -0.09404(9) 0.0271(3) Uani 1 1 d . . . H10A H 0.0089 0.5692 -0.0855 0.041 Uiso 1 1 calc R . . H10B H 0.0364 0.6420 -0.1537 0.041 Uiso 1 1 calc R . . H10C H 0.0239 0.8351 -0.0919 0.041 Uiso 1 1 calc R . . C11 C 0.08766(4) 0.6665(2) 0.07813(8) 0.0161(2) Uani 1 1 d . . . C12 C 0.10886(5) 0.4951(2) 0.14420(8) 0.0202(3) Uani 1 1 d . . . H12 H 0.1225 0.3579 0.1286 0.024 Uiso 1 1 calc R . . C13 C 0.11020(5) 0.5238(2) 0.23303(9) 0.0244(3) Uani 1 1 d . . . H13 H 0.1242 0.4047 0.2773 0.029 Uiso 1 1 calc R . . C14 C 0.09131(5) 0.7248(2) 0.25725(8) 0.0237(3) Uani 1 1 d . . . H14 H 0.0926 0.7447 0.3181 0.028 Uiso 1 1 calc R . . C15 C 0.07051(5) 0.8965(2) 0.19199(9) 0.0234(3) Uani 1 1 d . . . H15 H 0.0576 1.0348 0.2083 0.028 Uiso 1 1 calc R . . C16 C 0.06834(5) 0.8678(2) 0.10271(8) 0.0207(3) Uani 1 1 d . . . H16 H 0.0536 0.9859 0.0583 0.025 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 C1 0.0234(6) 0.0198(6) 0.0278(6) -0.0065(5) 0.0129(5) -0.0030(5) C2 0.0242(6) 0.0196(6) 0.0353(7) 0.0000(5) 0.0161(6) 0.0024(5) C3 0.0187(6) 0.0293(7) 0.0246(6) 0.0045(5) 0.0096(5) 0.0015(5) C4 0.0231(6) 0.0277(7) 0.0213(6) -0.0046(5) 0.0075(5) -0.0030(5) C5 0.0228(6) 0.0190(6) 0.0215(6) -0.0027(5) 0.0098(5) -0.0004(5) C6 0.0185(5) 0.0181(5) 0.0177(5) 0.0002(4) 0.0100(4) -0.0018(4) S7 0.02194(16) 0.01826(17) 0.01459(15) 0.00023(10) 0.00769(12) -0.00064(11) O8 0.0302(5) 0.0157(4) 0.0247(5) 0.0033(3) 0.0090(4) 0.0018(3) C9 0.0177(5) 0.0177(5) 0.0179(6) -0.0018(4) 0.0066(4) -0.0006(4) C10 0.0202(6) 0.0381(8) 0.0196(6) -0.0047(5) 0.0036(5) 0.0000(5) C11 0.0133(5) 0.0173(5) 0.0176(5) -0.0008(4) 0.0058(4) -0.0022(4) C12 0.0200(6) 0.0175(6) 0.0243(6) 0.0023(5) 0.0097(5) 0.0027(5) C13 0.0252(6) 0.0258(6) 0.0219(6) 0.0077(5) 0.0085(5) 0.0038(5) C14 0.0242(6) 0.0306(7) 0.0167(6) -0.0003(5) 0.0083(5) -0.0026(5) C15 0.0269(6) 0.0224(6) 0.0226(6) -0.0030(5) 0.0113(5) 0.0021(5) C16 0.0235(6) 0.0195(6) 0.0189(6) 0.0018(4) 0.0079(5) 0.0037(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 C1 C2 1.3879(19) . ? C1 C6 1.3890(17) . ? C1 H1 0.9500 . ? C2 C3 1.3889(19) . ? C2 H2 0.9500 . ? C3 C4 1.3834(18) . ? C3 H3 0.9500 . ? C4 C5 1.3932(18) . ? C4 H4 0.9500 . ? C5 C6 1.3850(17) . ? C5 H5 0.9500 . ? C6 S7 1.7868(12) . ? S7 O8 1.4991(9) . ? S7 C9 1.8492(12) . ? C9 C11 1.5044(16) . ? C9 C10 1.5279(16) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.3932(16) . ? C11 C16 1.3956(16) . ? C12 C13 1.3928(17) . ? C12 H12 0.9500 . ? C13 C14 1.3860(19) . ? C13 H13 0.9500 . ? C14 C15 1.3850(19) . ? C14 H14 0.9500 . ? C15 C16 1.3917(17) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.94(11) . . ? C2 C1 H1 120.5 . . ? C6 C1 H1 120.5 . . ? C1 C2 C3 120.34(12) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.14(12) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.15(12) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.11(12) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 121.31(11) . . ? C5 C6 S7 119.16(9) . . ? C1 C6 S7 119.33(9) . . ? O8 S7 C6 107.07(5) . . ? O8 S7 C9 107.93(5) . . ? C6 S7 C9 99.38(5) . . ? C11 C9 C10 114.88(10) . . ? C11 C9 S7 111.95(8) . . ? C10 C9 S7 105.86(8) . . ? C11 C9 H9 108.0 . . ? C10 C9 H9 108.0 . . ? S7 C9 H9 108.0 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 118.93(11) . . ? C12 C11 C9 119.52(10) . . ? C16 C11 C9 121.56(10) . . ? C13 C12 C11 120.36(11) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 120.46(11) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.40(11) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 120.53(12) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 120.31(11) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.53(18) . . . . ? C1 C2 C3 C4 1.19(19) . . . . ? C2 C3 C4 C5 -1.02(19) . . . . ? C3 C4 C5 C6 0.19(18) . . . . ? C4 C5 C6 C1 0.48(18) . . . . ? C4 C5 C6 S7 -174.49(9) . . . . ? C2 C1 C6 C5 -0.31(18) . . . . ? C2 C1 C6 S7 174.65(9) . . . . ? C5 C6 S7 O8 0.44(11) . . . . ? C1 C6 S7 O8 -174.63(9) . . . . ? C5 C6 S7 C9 -111.72(10) . . . . ? C1 C6 S7 C9 73.21(10) . . . . ? O8 S7 C9 C11 -52.37(9) . . . . ? C6 S7 C9 C11 59.12(9) . . . . ? O8 S7 C9 C10 73.51(9) . . . . ? C6 S7 C9 C10 -175.01(8) . . . . ? C10 C9 C11 C12 129.95(12) . . . . ? S7 C9 C11 C12 -109.28(11) . . . . ? C10 C9 C11 C16 -50.20(15) . . . . ? S7 C9 C11 C16 70.57(13) . . . . ? C16 C11 C12 C13 0.66(18) . . . . ? C9 C11 C12 C13 -179.49(11) . . . . ? C11 C12 C13 C14 -1.16(19) . . . . ? C12 C13 C14 C15 0.71(19) . . . . ? C13 C14 C15 C16 0.22(19) . . . . ? C14 C15 C16 C11 -0.71(19) . . . . ? C12 C11 C16 C15 0.27(18) . . . . ? C9 C11 C16 C15 -179.58(11) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.224 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.058 #===END============================================================== data_compound_24 _database_code_depnum_ccdc_archive 'CCDC 759291' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 F2 O S' _chemical_formula_sum 'C14 H12 F2 O S' _chemical_formula_weight 266.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 /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 15.5607(3) _cell_length_b 5.81098(11) _cell_length_c 14.3987(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.8650(10) _cell_angle_gamma 90.00 _cell_volume 1239.19(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8876 _cell_measurement_theta_min 7.8 _cell_measurement_theta_max 68.1 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 2.433 _exptl_absorpt_correction_T_min 0.652 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Abscor, Higashi ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Spider' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8951 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 7.34 _diffrn_reflns_theta_max 68.13 _reflns_number_total 2200 _reflns_number_gt 2005 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrystalClear, Rigaku ; _computing_cell_refinement ; CrystalClear, Rigaku ; _computing_data_reduction ; CrystalClear, Rigaku ; _computing_structure_solution ; SIR92, Altomare et al. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0680P)^2^+0.5050P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0063(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2200 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1088 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 S1 S 0.66431(3) -0.04942(7) 0.67566(3) 0.02086(19) Uani 1 1 d . . . F1 F 0.55179(7) 0.1659(2) 0.25744(7) 0.0334(3) Uani 1 1 d . . . F2 F 1.04308(7) 0.1735(2) 0.56921(8) 0.0370(3) Uani 1 1 d . . . O1 O 0.70575(8) -0.2849(2) 0.68483(9) 0.0275(3) Uani 1 1 d . . . C1 C 0.63685(10) 0.0287(3) 0.54945(12) 0.0200(4) Uani 1 1 d . . . C2 C 0.65631(13) -0.1249(4) 0.48534(13) 0.0300(4) Uani 1 1 d . . . H2 H 0.6886 -0.2624 0.5091 0.039 Uiso 1 1 calc R . . C3 C 0.62836(14) -0.0769(4) 0.38610(14) 0.0338(5) Uani 1 1 d . . . H3 H 0.6419 -0.1792 0.3411 0.044 Uiso 1 1 calc R . . C4 C 0.58095(11) 0.1207(3) 0.35469(13) 0.0247(4) Uani 1 1 d . . . C5 C 0.56156(12) 0.2782(4) 0.41692(14) 0.0294(4) Uani 1 1 d . . . H5 H 0.5296 0.4159 0.3927 0.038 Uiso 1 1 calc R . . C6 C 0.59003(13) 0.2297(4) 0.51601(14) 0.0291(4) Uani 1 1 d . . . H6 H 0.5774 0.3344 0.5608 0.038 Uiso 1 1 calc R . . C7 C 0.82954(10) 0.1544(3) 0.68170(11) 0.0201(4) Uani 1 1 d . . . C8 C 0.84192(11) 0.3433(3) 0.62722(12) 0.0236(4) Uani 1 1 d . . . H8 H 0.8011 0.4691 0.6167 0.031 Uiso 1 1 calc R . . C9 C 0.91327(12) 0.3497(3) 0.58810(13) 0.0269(4) Uani 1 1 d . . . H9 H 0.9218 0.4786 0.5513 0.035 Uiso 1 1 calc R . . C10 C 0.97098(11) 0.1650(3) 0.60401(13) 0.0265(4) Uani 1 1 d . . . C11 C 0.96055(12) -0.0266(3) 0.65612(13) 0.0262(4) Uani 1 1 d . . . H11 H 1.0012 -0.1526 0.6652 0.034 Uiso 1 1 calc R . . C12 C 0.88924(11) -0.0307(3) 0.69489(12) 0.0228(4) Uani 1 1 d . . . H12 H 0.8809 -0.1612 0.7309 0.030 Uiso 1 1 calc R . . C13 C 0.75525(11) 0.1595(3) 0.72834(12) 0.0209(4) Uani 1 1 d . . . H13 H 0.7279 0.3169 0.7184 0.027 Uiso 1 1 calc R . . C14 C 0.78804(12) 0.1120(4) 0.83849(13) 0.0297(4) Uani 1 1 d . . . H14A H 0.7364 0.1142 0.8640 0.039 Uiso 1 1 calc R . . H14B H 0.8315 0.2307 0.8713 0.039 Uiso 1 1 calc R . . H14C H 0.8171 -0.0394 0.8505 0.039 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 0.0197(3) 0.0216(3) 0.0212(3) 0.00186(15) 0.00619(17) 0.00071(15) F1 0.0377(6) 0.0383(8) 0.0197(6) 0.0030(4) 0.0024(4) -0.0033(5) F2 0.0301(6) 0.0475(8) 0.0386(7) -0.0131(5) 0.0180(5) -0.0122(5) O1 0.0322(7) 0.0198(7) 0.0294(7) 0.0043(5) 0.0080(5) 0.0024(5) C1 0.0149(8) 0.0221(9) 0.0206(8) 0.0000(7) 0.0019(6) -0.0024(6) C2 0.0361(10) 0.0235(10) 0.0262(10) -0.0020(8) 0.0034(8) 0.0073(8) C3 0.0428(11) 0.0313(12) 0.0251(10) -0.0064(8) 0.0075(8) 0.0070(9) C4 0.0201(8) 0.0302(10) 0.0205(9) 0.0013(7) 0.0014(6) -0.0058(7) C5 0.0293(9) 0.0278(10) 0.0285(10) 0.0046(8) 0.0050(7) 0.0070(8) C6 0.0317(9) 0.0303(11) 0.0253(9) -0.0006(8) 0.0087(7) 0.0084(8) C7 0.0183(8) 0.0224(10) 0.0155(8) -0.0021(6) -0.0009(6) -0.0019(7) C8 0.0231(8) 0.0229(10) 0.0199(8) -0.0004(7) -0.0005(6) 0.0005(7) C9 0.0312(9) 0.0288(11) 0.0184(8) -0.0001(7) 0.0039(7) -0.0074(8) C10 0.0209(8) 0.0360(12) 0.0222(9) -0.0097(7) 0.0061(7) -0.0091(7) C11 0.0190(8) 0.0282(10) 0.0286(9) -0.0065(8) 0.0030(7) -0.0002(7) C12 0.0202(8) 0.0233(10) 0.0215(9) -0.0005(7) 0.0014(7) 0.0002(7) C13 0.0207(8) 0.0198(10) 0.0198(8) -0.0011(6) 0.0025(6) 0.0013(6) C14 0.0267(9) 0.0414(12) 0.0192(9) -0.0003(8) 0.0045(7) 0.0059(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.5008(14) . ? S1 C1 1.7929(17) . ? S1 C13 1.8422(17) . ? F1 C4 1.359(2) . ? F2 C10 1.363(2) . ? C1 C2 1.383(3) . ? C1 C6 1.383(3) . ? C2 C3 1.388(3) . ? C3 C4 1.364(3) . ? C4 C5 1.378(3) . ? C5 C6 1.387(3) . ? C7 C12 1.396(2) . ? C7 C8 1.396(2) . ? C7 C13 1.505(2) . ? C8 C9 1.391(3) . ? C9 C10 1.373(3) . ? C10 C11 1.380(3) . ? C11 C12 1.387(3) . ? C13 C14 1.535(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 O1 S1 C1 106.40(8) . . ? O1 S1 C13 108.04(7) . . ? C1 S1 C13 99.48(8) . . ? C2 C1 C6 120.85(16) . . ? C2 C1 S1 118.71(14) . . ? C6 C1 S1 120.20(13) . . ? C1 C2 C3 119.59(18) . . ? C4 C3 C2 118.49(18) . . ? F1 C4 C3 118.69(17) . . ? F1 C4 C5 118.10(17) . . ? C3 C4 C5 123.20(17) . . ? C4 C5 C6 117.99(18) . . ? C1 C6 C5 119.85(18) . . ? C12 C7 C8 118.78(16) . . ? C12 C7 C13 121.67(16) . . ? C8 C7 C13 119.50(15) . . ? C9 C8 C7 120.90(16) . . ? C10 C9 C8 118.28(17) . . ? F2 C10 C9 118.71(17) . . ? F2 C10 C11 118.47(17) . . ? C9 C10 C11 122.80(17) . . ? C10 C11 C12 118.34(17) . . ? C11 C12 C7 120.89(17) . . ? C7 C13 C14 113.59(13) . . ? C7 C13 S1 113.66(11) . . ? C14 C13 S1 106.06(12) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 68.13 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.473 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.060 #===END============================================================== data_compound_25 _database_code_depnum_ccdc_archive 'CCDC 759292' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O3 S' _chemical_formula_sum 'C16 H18 O3 S' _chemical_formula_weight 290.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P n' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 8.5839(6) _cell_length_b 5.5077(3) _cell_length_c 15.7646(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.481(7) _cell_angle_gamma 90.00 _cell_volume 721.63(8) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4682 _cell_measurement_theta_min 5.2791 _cell_measurement_theta_max 67.5498 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 2.032 _exptl_absorpt_correction_T_min 0.38739 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 10.2673 _diffrn_measurement_device_type 'Gemini R Ultra' _diffrn_measurement_method 'thin slice \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6211 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 5.39 _diffrn_reflns_theta_max 67.68 _reflns_number_total 2330 _reflns_number_gt 2257 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0544P)^2^+0.1492P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.392(16) _chemical_absolute_configuration unk _refine_ls_number_reflns 2330 _refine_ls_number_parameters 185 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.41408(6) 0.42356(8) 0.45175(4) 0.02265(14) Uani 1 1 d . . . O2 O 0.4494(2) 0.2381(3) 0.86166(11) 0.0307(4) Uani 1 1 d . . . O3 O 0.44191(18) 0.6905(3) 0.46735(10) 0.0304(4) Uani 1 1 d . . . O4 O 0.55024(19) 0.2066(3) 0.10964(11) 0.0318(4) Uani 1 1 d . . . C5 C 0.5470(3) 0.5246(4) 0.31407(15) 0.0237(4) Uani 1 1 d . . . H5 H 0.5824 0.6712 0.3446 0.028 Uiso 1 1 calc R . . C6 C 0.5991(3) 0.4405(4) 0.67876(15) 0.0247(5) Uani 1 1 d . . . H6 H 0.6572 0.5761 0.6655 0.030 Uiso 1 1 calc R . . C7 C 0.4625(3) 0.0655(4) 0.63757(17) 0.0263(5) Uani 1 1 d . . . H7 H 0.4257 -0.0588 0.5956 0.032 Uiso 1 1 calc R . . C8 C 0.4055(3) 0.1435(4) 0.30541(15) 0.0232(4) Uani 1 1 d . . . H8 H 0.3459 0.0294 0.3298 0.028 Uiso 1 1 calc R . . C9 C 0.5260(3) 0.2664(4) 0.18940(14) 0.0237(5) Uani 1 1 d . . . C10 C 0.5853(2) 0.2656(4) 0.52686(14) 0.0222(4) Uani 1 1 d . . . H10 H 0.5889 0.0950 0.5057 0.027 Uiso 1 1 calc R . . C11 C 0.5647(3) 0.4270(4) 0.75911(16) 0.0250(5) Uani 1 1 d . . . H11 H 0.6006 0.5520 0.8010 0.030 Uiso 1 1 calc R . . C12 C 0.4378(3) 0.0989(4) 0.22460(16) 0.0239(5) Uani 1 1 d . . . H12 H 0.3997 -0.0456 0.1934 0.029 Uiso 1 1 calc R . . C13 C 0.5810(3) 0.4801(4) 0.23406(16) 0.0261(5) Uani 1 1 d . . . H13 H 0.6410 0.5941 0.2100 0.031 Uiso 1 1 calc R . . C14 C 0.7420(3) 0.3897(4) 0.52435(16) 0.0289(5) Uani 1 1 d . . . H14A H 0.7363 0.5619 0.5389 0.043 Uiso 1 1 calc R . . H14B H 0.7596 0.3744 0.4655 0.043 Uiso 1 1 calc R . . H14C H 0.8312 0.3128 0.5670 0.043 Uiso 1 1 calc R . . C15 C 0.4272(3) 0.0495(4) 0.71829(17) 0.0275(5) Uani 1 1 d . . . H15 H 0.3687 -0.0856 0.7317 0.033 Uiso 1 1 calc R . . C16 C 0.4780(2) 0.2326(4) 0.77978(14) 0.0239(5) Uani 1 1 d . . . C17 C 0.4612(2) 0.3556(4) 0.35008(14) 0.0210(4) Uani 1 1 d . . . C18 C 0.5500(3) 0.2577(4) 0.61597(15) 0.0226(4) Uani 1 1 d . . . C19 C 0.6429(3) 0.3741(5) 0.07156(17) 0.0350(6) Uani 1 1 d . . . H19A H 0.5866 0.5302 0.0608 0.053 Uiso 1 1 calc R . . H19B H 0.6563 0.3081 0.0161 0.053 Uiso 1 1 calc R . . H19C H 0.7489 0.3979 0.1120 0.053 Uiso 1 1 calc R . . C20 C 0.3839(3) 0.0243(5) 0.89078(18) 0.0347(5) Uani 1 1 d . . . H20A H 0.2761 -0.0060 0.8532 0.052 Uiso 1 1 calc R . . H20B H 0.3769 0.0468 0.9514 0.052 Uiso 1 1 calc R . . H20C H 0.4536 -0.1146 0.8877 0.052 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 0.0248(2) 0.0216(2) 0.0215(3) -0.0009(2) 0.00572(18) 0.0005(2) O2 0.0399(9) 0.0340(9) 0.0198(9) -0.0023(7) 0.0106(7) -0.0078(7) O3 0.0441(10) 0.0188(8) 0.0290(10) -0.0027(6) 0.0102(8) 0.0041(6) O4 0.0324(8) 0.0426(10) 0.0213(8) -0.0025(7) 0.0084(6) 0.0019(7) C5 0.0283(10) 0.0215(10) 0.0213(11) -0.0006(8) 0.0063(8) -0.0039(9) C6 0.0278(11) 0.0221(11) 0.0236(12) -0.0008(8) 0.0049(9) -0.0061(8) C7 0.0331(12) 0.0233(12) 0.0233(12) -0.0048(8) 0.0087(10) -0.0045(8) C8 0.0252(10) 0.0184(10) 0.0247(11) 0.0020(9) 0.0039(8) -0.0008(8) C9 0.0243(10) 0.0280(11) 0.0175(11) -0.0005(8) 0.0027(8) 0.0069(8) C10 0.0248(11) 0.0195(10) 0.0210(11) -0.0003(8) 0.0035(9) -0.0007(8) C11 0.0265(11) 0.0257(11) 0.0214(12) -0.0045(8) 0.0036(9) -0.0044(8) C12 0.0264(11) 0.0209(10) 0.0216(12) -0.0025(8) 0.0011(9) 0.0014(8) C13 0.0267(11) 0.0240(10) 0.0274(12) 0.0038(9) 0.0061(9) -0.0011(9) C14 0.0239(10) 0.0379(12) 0.0246(12) 0.0027(10) 0.0054(9) 0.0002(9) C15 0.0335(12) 0.0223(11) 0.0271(14) 0.0018(9) 0.0083(10) -0.0053(9) C16 0.0251(10) 0.0274(11) 0.0176(11) 0.0009(8) 0.0027(9) 0.0009(8) C17 0.0234(10) 0.0215(10) 0.0172(10) 0.0016(9) 0.0035(8) 0.0022(8) C18 0.0233(10) 0.0201(10) 0.0230(12) 0.0000(8) 0.0028(8) 0.0012(8) C19 0.0326(12) 0.0513(15) 0.0223(12) 0.0061(11) 0.0090(9) 0.0032(11) C20 0.0444(13) 0.0375(13) 0.0243(12) 0.0038(11) 0.0126(10) -0.0041(11) _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 O3 1.5001(16) . ? S1 C17 1.788(2) . ? S1 C10 1.857(2) . ? O2 C16 1.373(3) . ? O2 C20 1.430(3) . ? O4 C9 1.365(3) . ? O4 C19 1.444(3) . ? C5 C13 1.386(3) . ? C5 C17 1.393(3) . ? C6 C11 1.373(3) . ? C6 C18 1.401(3) . ? C7 C15 1.383(4) . ? C7 C18 1.389(3) . ? C8 C17 1.386(3) . ? C8 C12 1.391(3) . ? C9 C13 1.392(3) . ? C9 C12 1.394(3) . ? C10 C18 1.510(3) . ? C10 C14 1.518(3) . ? C11 C16 1.389(3) . ? C15 C16 1.391(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 O3 S1 C17 106.85(10) . . ? O3 S1 C10 106.65(9) . . ? C17 S1 C10 98.81(10) . . ? C16 O2 C20 117.44(17) . . ? C9 O4 C19 117.09(18) . . ? C13 C5 C17 120.4(2) . . ? C11 C6 C18 121.2(2) . . ? C15 C7 C18 122.1(2) . . ? C17 C8 C12 119.5(2) . . ? O4 C9 C13 124.0(2) . . ? O4 C9 C12 115.47(19) . . ? C13 C9 C12 120.5(2) . . ? C18 C10 C14 114.99(18) . . ? C18 C10 S1 107.21(14) . . ? C14 C10 S1 109.73(15) . . ? C6 C11 C16 120.6(2) . . ? C8 C12 C9 120.0(2) . . ? C5 C13 C9 119.2(2) . . ? C7 C15 C16 119.5(2) . . ? O2 C16 C11 115.84(19) . . ? O2 C16 C15 124.9(2) . . ? C11 C16 C15 119.2(2) . . ? C8 C17 C5 120.4(2) . . ? C8 C17 S1 120.38(17) . . ? C5 C17 S1 119.12(17) . . ? C7 C18 C6 117.4(2) . . ? C7 C18 C10 119.77(19) . . ? C6 C18 C10 122.82(19) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 66.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.199 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.043 #===END============================================================== data_compound_28 _database_code_depnum_ccdc_archive 'CCDC 759293' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 F2 O S' _chemical_formula_sum 'C14 H12 F2 O S' _chemical_formula_weight 266.30 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 'P 21/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 13.5661(5) _cell_length_b 5.7383(2) _cell_length_c 15.7552(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.6250(10) _cell_angle_gamma 90.00 _cell_volume 1224.03(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 13670 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.889 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The 1 0 2 and 0 0 2 reflections have been omitted due to the beamstop. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8959 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2796 _reflns_number_gt 2240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL--97; PLATON' _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^)+(0.0485P)^2^+0.4872P] 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 2796 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.68767(3) 0.12529(9) 0.61000(3) 0.04020(16) Uani 1 1 d . . . F1 F 0.90642(9) -0.1183(2) 0.96791(7) 0.0513(3) Uani 1 1 d . . . F3 F 0.54933(10) -0.0754(2) 0.25693(8) 0.0635(4) Uani 1 1 d . . . O1 O 0.70635(11) 0.3818(2) 0.61397(9) 0.0550(4) Uani 1 1 d . . . C1 C 0.65170(12) 0.0588(3) 0.50096(11) 0.0353(4) Uani 1 1 d . . . C2 C 0.83982(12) -0.0446(3) 0.71086(11) 0.0335(4) Uani 1 1 d . . . C3 C 0.66322(14) 0.2251(3) 0.43875(12) 0.0402(4) Uani 1 1 d . . . H3A H 0.6943 0.3695 0.4529 0.048 Uiso 1 1 calc R . . C4 C 0.60590(14) -0.1534(3) 0.48153(12) 0.0401(4) Uani 1 1 d . . . H4A H 0.5985 -0.2663 0.5248 0.048 Uiso 1 1 calc R . . C5 C 0.58358(14) -0.0299(4) 0.33798(12) 0.0431(4) Uani 1 1 d . . . C6 C 0.88140(14) 0.1149(4) 0.56528(12) 0.0433(4) Uani 1 1 d . . . H6A H 0.9479 0.0490 0.5745 0.065 Uiso 1 1 calc R . . H6B H 0.8822 0.2786 0.5830 0.065 Uiso 1 1 calc R . . H6C H 0.8600 0.1045 0.5048 0.065 Uiso 1 1 calc R . . C7 C 0.89863(14) 0.1195(3) 0.75531(12) 0.0420(4) Uani 1 1 d . . . H7A H 0.9233 0.2495 0.7259 0.050 Uiso 1 1 calc R . . C8 C 0.62899(15) 0.1795(3) 0.35523(13) 0.0446(4) Uani 1 1 d . . . H8A H 0.6369 0.2905 0.3114 0.054 Uiso 1 1 calc R . . C9 C 0.80497(14) -0.2335(3) 0.75521(12) 0.0409(4) Uani 1 1 d . . . H9A H 0.7652 -0.3472 0.7256 0.049 Uiso 1 1 calc R . . C10 C 0.57116(14) -0.1984(3) 0.39860(13) 0.0434(4) Uani 1 1 d . . . H10A H 0.5396 -0.3418 0.3839 0.052 Uiso 1 1 calc R . . C11 C 0.81021(12) -0.0206(3) 0.61716(11) 0.0348(4) Uani 1 1 d . . . H11A H 0.8022 -0.1803 0.5923 0.042 Uiso 1 1 calc R . . C12 C 0.82700(14) -0.2591(3) 0.84141(12) 0.0421(4) Uani 1 1 d . . . H12A H 0.8028 -0.3886 0.8714 0.051 Uiso 1 1 calc R . . C13 C 0.88479(13) -0.0928(3) 0.88291(11) 0.0370(4) Uani 1 1 d . . . C14 C 0.92158(15) 0.0951(3) 0.84213(12) 0.0446(5) Uani 1 1 d . . . H14A H 0.9619 0.2066 0.8724 0.053 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 0.0364(2) 0.0490(3) 0.0348(3) -0.00715(19) -0.00113(17) 0.00542(19) F1 0.0638(7) 0.0597(7) 0.0293(6) -0.0019(5) -0.0061(5) -0.0041(6) F3 0.0719(9) 0.0749(9) 0.0407(7) -0.0109(6) -0.0208(6) 0.0041(7) O1 0.0642(9) 0.0447(8) 0.0538(9) -0.0188(6) -0.0129(7) 0.0131(7) C1 0.0322(8) 0.0381(9) 0.0349(9) -0.0039(7) -0.0032(7) 0.0047(7) C2 0.0325(8) 0.0348(9) 0.0328(9) -0.0029(7) -0.0010(7) 0.0011(7) C3 0.0400(10) 0.0350(9) 0.0443(11) -0.0014(7) -0.0070(8) 0.0025(7) C4 0.0390(9) 0.0398(10) 0.0410(10) 0.0005(8) -0.0032(8) 0.0017(8) C5 0.0407(10) 0.0511(11) 0.0357(10) -0.0070(8) -0.0108(8) 0.0098(8) C6 0.0382(10) 0.0552(12) 0.0366(10) 0.0039(8) 0.0030(8) 0.0013(8) C7 0.0490(11) 0.0378(10) 0.0386(10) 0.0009(8) -0.0023(8) -0.0096(8) C8 0.0491(11) 0.0440(10) 0.0397(10) 0.0043(8) -0.0061(8) 0.0080(9) C9 0.0448(10) 0.0409(10) 0.0360(10) -0.0005(7) -0.0053(8) -0.0112(8) C10 0.0384(10) 0.0401(10) 0.0503(11) -0.0095(8) -0.0081(8) 0.0011(8) C11 0.0356(9) 0.0364(9) 0.0319(9) -0.0034(7) -0.0005(7) 0.0018(7) C12 0.0455(10) 0.0430(10) 0.0372(10) 0.0047(8) -0.0015(8) -0.0097(8) C13 0.0378(9) 0.0436(10) 0.0289(8) -0.0034(7) -0.0028(7) 0.0032(7) C14 0.0508(11) 0.0426(10) 0.0393(10) -0.0064(8) -0.0054(8) -0.0111(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4944(15) . ? S1 C1 1.7969(18) . ? S1 C11 1.8584(17) . ? F1 C13 1.3606(19) . ? F3 C5 1.356(2) . ? C1 C3 1.384(3) . ? C1 C4 1.393(3) . ? C2 C9 1.389(3) . ? C2 C7 1.394(2) . ? C2 C11 1.511(2) . ? C3 C8 1.392(3) . ? C3 H3A 0.9500 . ? C4 C10 1.385(3) . ? C4 H4A 0.9500 . ? C5 C8 1.370(3) . ? C5 C10 1.377(3) . ? C6 C11 1.518(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C14 1.391(3) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 C12 1.380(3) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 H11A 1.0000 . ? C12 C13 1.374(3) . ? C12 H12A 0.9500 . ? C13 C14 1.366(3) . ? C14 H14A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 C1 106.51(8) . . ? O1 S1 C11 107.01(8) . . ? C1 S1 C11 98.64(8) . . ? C3 C1 C4 121.08(17) . . ? C3 C1 S1 119.66(14) . . ? C4 C1 S1 119.09(14) . . ? C9 C2 C7 118.47(16) . . ? C9 C2 C11 118.98(15) . . ? C7 C2 C11 122.53(16) . . ? C1 C3 C8 119.61(18) . . ? C1 C3 H3A 120.2 . . ? C8 C3 H3A 120.2 . . ? C10 C4 C1 119.39(18) . . ? C10 C4 H4A 120.3 . . ? C1 C4 H4A 120.3 . . ? F3 C5 C8 118.60(18) . . ? F3 C5 C10 117.92(18) . . ? C8 C5 C10 123.47(18) . . ? C11 C6 H6A 109.5 . . ? C11 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C11 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C14 C7 C2 120.80(17) . . ? C14 C7 H7A 119.6 . . ? C2 C7 H7A 119.6 . . ? C5 C8 C3 118.12(18) . . ? C5 C8 H8A 120.9 . . ? C3 C8 H8A 120.9 . . ? C12 C9 C2 121.26(16) . . ? C12 C9 H9A 119.4 . . ? C2 C9 H9A 119.4 . . ? C5 C10 C4 118.33(18) . . ? C5 C10 H10A 120.8 . . ? C4 C10 H10A 120.8 . . ? C2 C11 C6 115.70(14) . . ? C2 C11 S1 106.37(11) . . ? C6 C11 S1 109.49(12) . . ? C2 C11 H11A 108.4 . . ? C6 C11 H11A 108.4 . . ? S1 C11 H11A 108.4 . . ? C13 C12 C9 118.42(17) . . ? C13 C12 H12A 120.8 . . ? C9 C12 H12A 120.8 . . ? F1 C13 C14 119.06(16) . . ? F1 C13 C12 118.32(16) . . ? C14 C13 C12 122.62(17) . . ? C13 C14 C7 118.44(17) . . ? C13 C14 H14A 120.8 . . ? C7 C14 H14A 120.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C1 C3 11.42(17) . . . . ? C11 S1 C1 C3 -99.28(15) . . . . ? O1 S1 C1 C4 -163.85(14) . . . . ? C11 S1 C1 C4 85.44(15) . . . . ? C4 C1 C3 C8 -0.3(3) . . . . ? S1 C1 C3 C8 -175.51(14) . . . . ? C3 C1 C4 C10 -0.1(3) . . . . ? S1 C1 C4 C10 175.07(14) . . . . ? C9 C2 C7 C14 -0.3(3) . . . . ? C11 C2 C7 C14 177.86(17) . . . . ? F3 C5 C8 C3 179.54(17) . . . . ? C10 C5 C8 C3 -0.8(3) . . . . ? C1 C3 C8 C5 0.8(3) . . . . ? C7 C2 C9 C12 0.5(3) . . . . ? C11 C2 C9 C12 -177.73(17) . . . . ? F3 C5 C10 C4 -179.99(16) . . . . ? C8 C5 C10 C4 0.4(3) . . . . ? C1 C4 C10 C5 0.1(3) . . . . ? C9 C2 C11 C6 -154.06(17) . . . . ? C7 C2 C11 C6 27.8(2) . . . . ? C9 C2 C11 S1 84.12(17) . . . . ? C7 C2 C11 S1 -93.99(18) . . . . ? O1 S1 C11 C2 85.78(13) . . . . ? C1 S1 C11 C2 -163.91(12) . . . . ? O1 S1 C11 C6 -39.91(14) . . . . ? C1 S1 C11 C6 70.40(13) . . . . ? C2 C9 C12 C13 -0.1(3) . . . . ? C9 C12 C13 F1 179.99(17) . . . . ? C9 C12 C13 C14 -0.4(3) . . . . ? F1 C13 C14 C7 -179.79(17) . . . . ? C12 C13 C14 C7 0.6(3) . . . . ? C2 C7 C14 C13 -0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.238 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.064 #===END============================================================== data_compound_29 _database_code_depnum_ccdc_archive 'CCDC 759294' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O3 S' _chemical_formula_sum 'C16 H18 O3 S' _chemical_formula_weight 290.36 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' 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 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 7.1117(12) _cell_length_b 8.5497(7) _cell_length_c 23.495(2) _cell_angle_alpha 89.756(7) _cell_angle_beta 89.579(10) _cell_angle_gamma 89.428(10) _cell_volume 1428.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9775 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 30.14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9339 _exptl_absorpt_correction_T_max 0.9553 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Ultra (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini R Ultra' _diffrn_measurement_method 'thin slice \w scans' _diffrn_detector_area_resol_mean 10.2673 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21334 _diffrn_reflns_av_R_equivalents 0.0116 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 30.14 _reflns_number_total 8198 _reflns_number_gt 7513 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, (Spek, 2002)' _computing_publication_material 'SHELXL-97; PLATON' _refine_special_details ; Note that refinement in P21/c (as suggested by PLATON) has several problems associated with it, including very large observed systematic absences, Rint = 0.17 and refines to R1 = 0.10, wR2 = 0.31. 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^)+(0.0338P)^2^+0.8990P] 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 8198 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 0.15894(18) 0.69483(13) 0.42792(5) 0.0162(2) Uani 1 1 d . . . H1A H 0.2682 0.7480 0.4437 0.024 Uiso 1 1 calc R . . H1B H 0.0516 0.7068 0.4540 0.024 Uiso 1 1 calc R . . H1C H 0.1275 0.7411 0.3909 0.024 Uiso 1 1 calc R . . O2 O 0.20200(13) 0.53200(9) 0.42087(3) 0.01466(16) Uani 1 1 d . . . C3 C 0.24784(16) 0.44791(13) 0.46816(5) 0.0123(2) Uani 1 1 d . . . C4 C 0.26163(16) 0.50825(14) 0.52294(5) 0.0144(2) Uani 1 1 d . . . H4 H 0.2376 0.6161 0.5296 0.017 Uiso 1 1 calc R . . C5 C 0.31091(17) 0.40935(15) 0.56785(5) 0.0169(2) Uani 1 1 d . . . H5 H 0.3192 0.4505 0.6052 0.020 Uiso 1 1 calc R . . C6 C 0.34817(17) 0.25138(15) 0.55878(5) 0.0171(2) Uani 1 1 d . . . H6 H 0.3830 0.1853 0.5896 0.020 Uiso 1 1 calc R . . C7 C 0.33391(17) 0.19080(14) 0.50384(5) 0.0152(2) Uani 1 1 d . . . H7 H 0.3595 0.0831 0.4972 0.018 Uiso 1 1 calc R . . C8 C 0.28233(16) 0.28809(13) 0.45903(5) 0.0125(2) Uani 1 1 d . . . S9 S 0.27360(4) 0.21135(3) 0.387898(12) 0.01390(6) Uani 1 1 d . . . O10 O 0.33044(14) 0.04245(10) 0.39252(4) 0.02112(19) Uani 1 1 d . . . C11 C 0.01379(16) 0.21669(13) 0.37918(5) 0.0126(2) Uani 1 1 d . . . H11 H -0.0325 0.3248 0.3881 0.015 Uiso 1 1 calc R . . C12 C -0.07861(18) 0.10342(14) 0.42050(5) 0.0169(2) Uani 1 1 d . . . H12A H -0.0255 -0.0017 0.4149 0.025 Uiso 1 1 calc R . . H12B H -0.2143 0.1017 0.4137 0.025 Uiso 1 1 calc R . . H12C H -0.0556 0.1371 0.4596 0.025 Uiso 1 1 calc R . . C13 C -0.02416(16) 0.18424(13) 0.31715(5) 0.0127(2) Uani 1 1 d . . . C14 C -0.04592(19) 0.03269(14) 0.29669(5) 0.0174(2) Uani 1 1 d . . . H14 H -0.0388 -0.0530 0.3225 0.021 Uiso 1 1 calc R . . C15 C -0.07794(19) 0.00407(15) 0.23922(5) 0.0194(2) Uani 1 1 d . . . H15 H -0.0923 -0.1000 0.2260 0.023 Uiso 1 1 calc R . . C16 C -0.08860(18) 0.12890(15) 0.20159(5) 0.0173(2) Uani 1 1 d . . . H16 H -0.1098 0.1099 0.1624 0.021 Uiso 1 1 calc R . . C17 C -0.06865(17) 0.28196(14) 0.22052(5) 0.0157(2) Uani 1 1 d . . . H17 H -0.0774 0.3670 0.1945 0.019 Uiso 1 1 calc R . . C18 C -0.03566(16) 0.30935(13) 0.27815(5) 0.0134(2) Uani 1 1 d . . . O19 O -0.01445(14) 0.45450(10) 0.30096(4) 0.01911(18) Uani 1 1 d . . . C20 C -0.0273(2) 0.58577(15) 0.26330(6) 0.0231(3) Uani 1 1 d . . . H20A H -0.1522 0.5891 0.2460 0.035 Uiso 1 1 calc R . . H20B H 0.0688 0.5760 0.2334 0.035 Uiso 1 1 calc R . . H20C H -0.0071 0.6822 0.2847 0.035 Uiso 1 1 calc R . . C21 C 0.65846(18) 1.19429(13) 0.06936(5) 0.0162(2) Uani 1 1 d . . . H21A H 0.5519 1.2055 0.0434 0.024 Uiso 1 1 calc R . . H21B H 0.7672 1.2495 0.0536 0.024 Uiso 1 1 calc R . . H21C H 0.6246 1.2389 0.1064 0.024 Uiso 1 1 calc R . . O22 O 0.70465(13) 1.03182(10) 0.07618(3) 0.01452(16) Uani 1 1 d . . . C23 C 0.75014(16) 0.94876(13) 0.02867(5) 0.0119(2) Uani 1 1 d . . . C24 C 0.76296(16) 1.01013(14) -0.02618(5) 0.0141(2) Uani 1 1 d . . . H24 H 0.7386 1.1181 -0.0328 0.017 Uiso 1 1 calc R . . C25 C 0.81190(17) 0.91192(15) -0.07138(5) 0.0166(2) Uani 1 1 d . . . H25 H 0.8199 0.9539 -0.1088 0.020 Uiso 1 1 calc R . . C26 C 0.84902(17) 0.75392(15) -0.06255(5) 0.0168(2) Uani 1 1 d . . . H26 H 0.8827 0.6884 -0.0936 0.020 Uiso 1 1 calc R . . C27 C 0.83624(16) 0.69245(14) -0.00749(5) 0.0148(2) Uani 1 1 d . . . H27 H 0.8621 0.5847 -0.0009 0.018 Uiso 1 1 calc R . . C28 C 0.78580(16) 0.78876(13) 0.03759(5) 0.0123(2) Uani 1 1 d . . . S29 S 0.78221(4) 0.71203(3) 0.108902(12) 0.01405(6) Uani 1 1 d . . . O30 O 0.84086(14) 0.54361(11) 0.10429(4) 0.02152(19) Uani 1 1 d . . . C31 C 0.52339(16) 0.71560(13) 0.12024(5) 0.0126(2) Uani 1 1 d . . . H31 H 0.4755 0.8230 0.1110 0.015 Uiso 1 1 calc R . . C32 C 0.42842(18) 0.60030(14) 0.08102(5) 0.0171(2) Uani 1 1 d . . . H32A H 0.2931 0.5994 0.0891 0.026 Uiso 1 1 calc R . . H32B H 0.4813 0.4954 0.0873 0.026 Uiso 1 1 calc R . . H32C H 0.4496 0.6317 0.0413 0.026 Uiso 1 1 calc R . . C33 C 0.49046(16) 0.68564(13) 0.18301(5) 0.0126(2) Uani 1 1 d . . . C34 C 0.48976(19) 0.53442(14) 0.20533(5) 0.0174(2) Uani 1 1 d . . . H34 H 0.5088 0.4481 0.1806 0.021 Uiso 1 1 calc R . . C35 C 0.4617(2) 0.50740(15) 0.26320(5) 0.0200(2) Uani 1 1 d . . . H35 H 0.4617 0.4036 0.2778 0.024 Uiso 1 1 calc R . . C36 C 0.43352(18) 0.63340(15) 0.29937(5) 0.0176(2) Uani 1 1 d . . . H36 H 0.4134 0.6152 0.3388 0.021 Uiso 1 1 calc R . . C37 C 0.43439(17) 0.78590(14) 0.27869(5) 0.0159(2) Uani 1 1 d . . . H37 H 0.4159 0.8715 0.3038 0.019 Uiso 1 1 calc R . . C38 C 0.46263(16) 0.81202(13) 0.22060(5) 0.0132(2) Uani 1 1 d . . . O39 O 0.46451(14) 0.95662(10) 0.19593(4) 0.01861(18) Uani 1 1 d . . . C40 C 0.4339(2) 1.08868(15) 0.23219(6) 0.0228(3) Uani 1 1 d . . . H40A H 0.5338 1.0926 0.2606 0.034 Uiso 1 1 calc R . . H40B H 0.3118 1.0791 0.2514 0.034 Uiso 1 1 calc R . . H40C H 0.4351 1.1848 0.2093 0.034 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 C1 0.0176(5) 0.0109(5) 0.0200(5) 0.0008(4) 0.0008(4) 0.0023(4) O2 0.0213(4) 0.0104(4) 0.0123(4) 0.0016(3) 0.0001(3) 0.0019(3) C3 0.0110(5) 0.0126(5) 0.0133(5) 0.0012(4) 0.0007(4) -0.0004(4) C4 0.0133(5) 0.0151(5) 0.0149(5) -0.0021(4) 0.0003(4) -0.0002(4) C5 0.0143(5) 0.0232(6) 0.0132(5) -0.0003(4) -0.0015(4) -0.0010(4) C6 0.0143(5) 0.0207(6) 0.0162(5) 0.0043(4) -0.0027(4) -0.0008(4) C7 0.0133(5) 0.0139(5) 0.0183(5) 0.0022(4) -0.0010(4) 0.0006(4) C8 0.0123(5) 0.0128(5) 0.0125(5) -0.0007(4) 0.0005(4) -0.0001(4) S9 0.01595(13) 0.01242(12) 0.01329(13) -0.00154(9) 0.00121(10) 0.00200(10) O10 0.0255(5) 0.0141(4) 0.0236(5) -0.0039(3) -0.0017(4) 0.0075(3) C11 0.0155(5) 0.0108(5) 0.0114(5) -0.0007(4) 0.0002(4) 0.0011(4) C12 0.0223(6) 0.0151(5) 0.0132(5) 0.0012(4) 0.0022(4) -0.0030(4) C13 0.0148(5) 0.0117(5) 0.0115(5) -0.0003(4) -0.0002(4) 0.0008(4) C14 0.0261(6) 0.0117(5) 0.0144(5) -0.0004(4) -0.0022(4) 0.0010(4) C15 0.0269(6) 0.0147(5) 0.0167(5) -0.0041(4) -0.0036(5) 0.0011(5) C16 0.0183(6) 0.0212(6) 0.0123(5) -0.0023(4) -0.0017(4) 0.0026(4) C17 0.0162(5) 0.0181(5) 0.0128(5) 0.0025(4) -0.0009(4) 0.0013(4) C18 0.0142(5) 0.0120(5) 0.0139(5) 0.0000(4) -0.0002(4) 0.0002(4) O19 0.0316(5) 0.0097(4) 0.0161(4) 0.0023(3) -0.0048(4) -0.0012(3) C20 0.0317(7) 0.0131(5) 0.0247(6) 0.0070(5) -0.0090(5) -0.0021(5) C21 0.0180(6) 0.0114(5) 0.0191(5) -0.0016(4) -0.0016(4) 0.0024(4) O22 0.0203(4) 0.0111(4) 0.0121(4) -0.0013(3) -0.0004(3) 0.0019(3) C23 0.0104(5) 0.0128(5) 0.0126(5) -0.0013(4) -0.0001(4) -0.0009(4) C24 0.0127(5) 0.0151(5) 0.0143(5) 0.0020(4) -0.0002(4) -0.0005(4) C25 0.0144(5) 0.0233(6) 0.0122(5) 0.0011(4) 0.0015(4) -0.0008(4) C26 0.0147(5) 0.0213(6) 0.0144(5) -0.0039(4) 0.0028(4) 0.0001(4) C27 0.0128(5) 0.0142(5) 0.0173(5) -0.0022(4) 0.0010(4) 0.0010(4) C28 0.0115(5) 0.0136(5) 0.0119(5) 0.0009(4) 0.0000(4) 0.0002(4) S29 0.01547(13) 0.01334(13) 0.01328(13) 0.00204(9) -0.00069(10) 0.00201(10) O30 0.0259(5) 0.0151(4) 0.0233(5) 0.0046(3) 0.0033(4) 0.0080(4) C31 0.0152(5) 0.0107(5) 0.0119(5) 0.0013(4) 0.0011(4) 0.0011(4) C32 0.0226(6) 0.0151(5) 0.0136(5) -0.0012(4) -0.0023(4) -0.0036(4) C33 0.0140(5) 0.0127(5) 0.0109(5) 0.0004(4) 0.0005(4) 0.0001(4) C34 0.0253(6) 0.0125(5) 0.0143(5) 0.0005(4) 0.0029(4) 0.0012(4) C35 0.0277(7) 0.0163(5) 0.0159(5) 0.0052(4) 0.0027(5) 0.0012(5) C36 0.0185(6) 0.0230(6) 0.0112(5) 0.0023(4) 0.0011(4) 0.0015(5) C37 0.0161(5) 0.0184(5) 0.0132(5) -0.0026(4) 0.0013(4) 0.0004(4) C38 0.0133(5) 0.0123(5) 0.0139(5) -0.0003(4) 0.0003(4) -0.0004(4) O39 0.0301(5) 0.0095(4) 0.0162(4) -0.0013(3) 0.0046(3) -0.0001(3) C40 0.0308(7) 0.0124(5) 0.0251(6) -0.0053(4) 0.0068(5) 0.0001(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 C1 O2 1.4326(14) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C3 1.3607(13) . ? C3 C4 1.3932(16) . ? C3 C8 1.4030(15) . ? C4 C5 1.3939(16) . ? C4 H4 0.9500 . ? C5 C6 1.3907(18) . ? C5 H5 0.9500 . ? C6 C7 1.3976(17) . ? C6 H6 0.9500 . ? C7 C8 1.3882(16) . ? C7 H7 0.9500 . ? C8 S9 1.7997(12) . ? S9 O10 1.4994(9) . ? S9 C11 1.8606(12) . ? C11 C13 1.5114(15) . ? C11 C12 1.5190(16) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.3943(16) . ? C13 C18 1.4077(15) . ? C14 C15 1.3941(17) . ? C14 H14 0.9500 . ? C15 C16 1.3848(17) . ? C15 H15 0.9500 . ? C16 C17 1.3928(17) . ? C16 H16 0.9500 . ? C17 C18 1.3971(16) . ? C17 H17 0.9500 . ? C18 O19 1.3640(14) . ? O19 C20 1.4288(14) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 O22 1.4328(14) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? O22 C23 1.3608(14) . ? C23 C24 1.3921(16) . ? C23 C28 1.4039(15) . ? C24 C25 1.3966(17) . ? C24 H24 0.9500 . ? C25 C26 1.3889(18) . ? C25 H25 0.9500 . ? C26 C27 1.3970(17) . ? C26 H26 0.9500 . ? C27 C28 1.3871(16) . ? C27 H27 0.9500 . ? C28 S29 1.7969(12) . ? S29 O30 1.4993(9) . ? S29 C31 1.8579(12) . ? C31 C33 1.5126(15) . ? C31 C32 1.5191(16) . ? C31 H31 1.0000 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.3932(16) . ? C33 C38 1.4099(16) . ? C34 C35 1.3915(17) . ? C34 H34 0.9500 . ? C35 C36 1.3870(18) . ? C35 H35 0.9500 . ? C36 C37 1.3895(17) . ? C36 H36 0.9500 . ? C37 C38 1.3956(16) . ? C37 H37 0.9500 . ? C38 O39 1.3634(14) . ? O39 C40 1.4313(15) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? 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 O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O2 C1 117.69(9) . . ? O2 C3 C4 125.27(10) . . ? O2 C3 C8 115.22(10) . . ? C4 C3 C8 119.52(10) . . ? C3 C4 C5 119.59(11) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 121.03(11) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.37(11) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 119.95(11) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C3 120.53(10) . . ? C7 C8 S9 119.78(9) . . ? C3 C8 S9 119.58(8) . . ? O10 S9 C8 106.01(5) . . ? O10 S9 C11 106.86(5) . . ? C8 S9 C11 97.93(5) . . ? C13 C11 C12 114.56(10) . . ? C13 C11 S9 106.73(8) . . ? C12 C11 S9 110.24(8) . . ? C13 C11 H11 108.4 . . ? C12 C11 H11 108.4 . . ? S9 C11 H11 108.4 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 118.25(10) . . ? C14 C13 C11 122.01(10) . . ? C18 C13 C11 119.73(10) . . ? C15 C14 C13 121.48(11) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 C15 C14 119.29(11) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 120.85(11) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C18 119.41(11) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? O19 C18 C17 123.97(10) . . ? O19 C18 C13 115.31(10) . . ? C17 C18 C13 120.71(11) . . ? C18 O19 C20 117.57(10) . . ? O19 C20 H20A 109.5 . . ? O19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O22 C21 H21A 109.5 . . ? O22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 O22 C21 117.84(9) . . ? O22 C23 C24 125.28(10) . . ? O22 C23 C28 115.34(10) . . ? C24 C23 C28 119.37(10) . . ? C23 C24 C25 119.56(11) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C26 C25 C24 121.13(11) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C27 119.27(11) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C28 C27 C26 120.01(11) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C23 120.65(10) . . ? C27 C28 S29 119.94(9) . . ? C23 C28 S29 119.26(9) . . ? O30 S29 C28 106.05(5) . . ? O30 S29 C31 106.98(6) . . ? C28 S29 C31 97.96(5) . . ? C33 C31 C32 114.57(10) . . ? C33 C31 S29 106.55(8) . . ? C32 C31 S29 110.65(8) . . ? C33 C31 H31 108.3 . . ? C32 C31 H31 108.3 . . ? S29 C31 H31 108.3 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C38 118.38(10) . . ? C34 C33 C31 121.44(10) . . ? C38 C33 C31 120.18(10) . . ? C35 C34 C33 121.28(11) . . ? C35 C34 H34 119.4 . . ? C33 C34 H34 119.4 . . ? C36 C35 C34 119.38(11) . . ? C36 C35 H35 120.3 . . ? C34 C35 H35 120.3 . . ? C35 C36 C37 120.96(11) . . ? C35 C36 H36 119.5 . . ? C37 C36 H36 119.5 . . ? C36 C37 C38 119.31(11) . . ? C36 C37 H37 120.3 . . ? C38 C37 H37 120.3 . . ? O39 C38 C37 123.99(11) . . ? O39 C38 C33 115.32(10) . . ? C37 C38 C33 120.70(11) . . ? C38 O39 C40 117.44(10) . . ? O39 C40 H40A 109.5 . . ? O39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 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 C1 O2 C3 C4 -1.92(17) . . . . ? C1 O2 C3 C8 177.91(10) . . . . ? O2 C3 C4 C5 -179.67(11) . . . . ? C8 C3 C4 C5 0.50(17) . . . . ? C3 C4 C5 C6 0.55(18) . . . . ? C4 C5 C6 C7 -0.69(18) . . . . ? C5 C6 C7 C8 -0.22(18) . . . . ? C6 C7 C8 C3 1.27(18) . . . . ? C6 C7 C8 S9 177.44(9) . . . . ? O2 C3 C8 C7 178.75(10) . . . . ? C4 C3 C8 C7 -1.41(17) . . . . ? O2 C3 C8 S9 2.57(14) . . . . ? C4 C3 C8 S9 -177.59(9) . . . . ? C7 C8 S9 O10 -0.34(11) . . . . ? C3 C8 S9 O10 175.86(9) . . . . ? C7 C8 S9 C11 109.81(10) . . . . ? C3 C8 S9 C11 -73.98(10) . . . . ? O10 S9 C11 C13 -80.87(8) . . . . ? C8 S9 C11 C13 169.67(8) . . . . ? O10 S9 C11 C12 44.12(9) . . . . ? C8 S9 C11 C12 -65.34(9) . . . . ? C12 C11 C13 C14 -33.36(16) . . . . ? S9 C11 C13 C14 88.94(12) . . . . ? C12 C11 C13 C18 147.55(11) . . . . ? S9 C11 C13 C18 -90.14(11) . . . . ? C18 C13 C14 C15 0.12(19) . . . . ? C11 C13 C14 C15 -178.98(12) . . . . ? C13 C14 C15 C16 -0.1(2) . . . . ? C14 C15 C16 C17 -0.3(2) . . . . ? C15 C16 C17 C18 0.62(19) . . . . ? C16 C17 C18 O19 -179.88(11) . . . . ? C16 C17 C18 C13 -0.58(18) . . . . ? C14 C13 C18 O19 179.57(11) . . . . ? C11 C13 C18 O19 -1.32(16) . . . . ? C14 C13 C18 C17 0.21(18) . . . . ? C11 C13 C18 C17 179.33(11) . . . . ? C17 C18 O19 C20 0.10(18) . . . . ? C13 C18 O19 C20 -179.24(11) . . . . ? C21 O22 C23 C24 2.71(17) . . . . ? C21 O22 C23 C28 -177.24(10) . . . . ? O22 C23 C24 C25 179.73(11) . . . . ? C28 C23 C24 C25 -0.31(17) . . . . ? C23 C24 C25 C26 -0.32(18) . . . . ? C24 C25 C26 C27 0.28(18) . . . . ? C25 C26 C27 C28 0.40(18) . . . . ? C26 C27 C28 C23 -1.04(17) . . . . ? C26 C27 C28 S29 -176.52(9) . . . . ? O22 C23 C28 C27 -179.05(10) . . . . ? C24 C23 C28 C27 1.00(17) . . . . ? O22 C23 C28 S29 -3.54(14) . . . . ? C24 C23 C28 S29 176.51(9) . . . . ? C27 C28 S29 O30 0.20(11) . . . . ? C23 C28 S29 O30 -175.34(9) . . . . ? C27 C28 S29 C31 -110.11(10) . . . . ? C23 C28 S29 C31 74.35(10) . . . . ? O30 S29 C31 C33 81.76(8) . . . . ? C28 S29 C31 C33 -168.69(8) . . . . ? O30 S29 C31 C32 -43.37(9) . . . . ? C28 S29 C31 C32 66.18(9) . . . . ? C32 C31 C33 C34 39.76(16) . . . . ? S29 C31 C33 C34 -82.95(12) . . . . ? C32 C31 C33 C38 -141.30(11) . . . . ? S29 C31 C33 C38 95.99(11) . . . . ? C38 C33 C34 C35 0.26(19) . . . . ? C31 C33 C34 C35 179.22(12) . . . . ? C33 C34 C35 C36 0.1(2) . . . . ? C34 C35 C36 C37 -0.5(2) . . . . ? C35 C36 C37 C38 0.49(19) . . . . ? C36 C37 C38 O39 179.45(11) . . . . ? C36 C37 C38 C33 -0.12(18) . . . . ? C34 C33 C38 O39 -179.85(11) . . . . ? C31 C33 C38 O39 1.18(16) . . . . ? C34 C33 C38 C37 -0.25(18) . . . . ? C31 C33 C38 C37 -179.22(11) . . . . ? C37 C38 O39 C40 -0.56(18) . . . . ? C33 C38 O39 C40 179.03(11) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 30.14 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.621 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.051 #===END============================================================== data_compound_30 _database_code_depnum_ccdc_archive 'CCDC 759295' #TrackingRef 'Maguire_CrysEngComm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O3 S' _chemical_formula_sum 'C16 H18 O3 S' _chemical_formula_weight 290.36 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' 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 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 12.4822(15) _cell_length_b 8.0394(9) _cell_length_c 14.9907(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1504.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.27 _cell_measurement_theta_max 13.25 _exptl_crystal_description tetrahderon _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The abolsute structure was determining using TWIN and BASF in Shelxl-97. For the correct structure BASF refined to 0.074, with R1 = 0.052, wR2 = 0.132. For the incorrect structure BASF refined to 0.926, with R1 = 0.053, wR2 = 0.133. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius MACH3' _diffrn_measurement_method '\w-\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3012 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0900 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.47 _reflns_number_total 2800 _reflns_number_gt 1783 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'PLATON (Spek, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL_97; PLATON' _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^)+(0.0653P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 2800 _refine_ls_number_parameters 184 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1368 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 C1 C 1.0224(5) 1.0648(8) 0.6489(4) 0.0846(19) Uani 1 1 d . . . H1A H 1.0103 1.1642 0.6148 0.127 Uiso 1 1 calc R . . H1B H 1.0918 1.0701 0.6764 0.127 Uiso 1 1 calc R . . H1C H 0.9684 1.0551 0.6942 0.127 Uiso 1 1 calc R . . O2 O 1.0175(3) 0.9229(5) 0.5910(2) 0.0701(10) Uani 1 1 d . . . C3 C 0.9305(3) 0.9052(6) 0.5378(3) 0.0495(12) Uani 1 1 d . . . C4 C 0.8363(4) 0.9947(6) 0.5463(3) 0.0459(11) Uani 1 1 d . . . H4 H 0.8300 1.0756 0.5903 0.055 Uiso 1 1 calc R . . C5 C 0.7509(4) 0.9633(6) 0.4888(3) 0.0447(11) Uani 1 1 d . . . H5 H 0.6880 1.0241 0.4951 0.054 Uiso 1 1 calc R . . C6 C 0.7573(3) 0.8446(5) 0.4230(3) 0.0398(11) Uani 1 1 d . . . C7 C 0.8518(3) 0.7543(6) 0.4169(3) 0.0561(14) Uani 1 1 d . . . H7 H 0.8577 0.6719 0.3736 0.067 Uiso 1 1 calc R . . C8 C 0.9366(4) 0.7830(7) 0.4727(4) 0.0628(14) Uani 1 1 d . . . H8 H 0.9988 0.7202 0.4669 0.075 Uiso 1 1 calc R . . C9 C 0.6648(3) 0.8148(5) 0.3607(3) 0.0450(11) Uani 1 1 d . . . H9 H 0.6132 0.9055 0.3685 0.054 Uiso 1 1 calc R . . C10 C 0.6952(4) 0.8071(7) 0.2635(3) 0.0616(14) Uani 1 1 d . . . H10A H 0.7328 0.9067 0.2473 0.092 Uiso 1 1 calc R . . H10B H 0.6316 0.7972 0.2278 0.092 Uiso 1 1 calc R . . H10C H 0.7405 0.7124 0.2534 0.092 Uiso 1 1 calc R . . S11 S 0.59920(8) 0.61813(13) 0.39502(7) 0.0464(3) Uani 1 1 d . . . O12 O 0.5594(3) 0.6458(5) 0.4867(2) 0.0649(10) Uani 1 1 d . . . C13 C 0.4849(3) 0.6253(5) 0.3223(3) 0.0393(10) Uani 1 1 d . . . C14 C 0.3953(4) 0.7186(5) 0.3466(3) 0.0452(10) Uani 1 1 d . . . H14 H 0.3947 0.7787 0.3996 0.054 Uiso 1 1 calc R . . C15 C 0.3082(4) 0.7202(6) 0.2909(3) 0.0477(12) Uani 1 1 d . . . H15 H 0.2478 0.7811 0.3067 0.057 Uiso 1 1 calc R . . C16 C 0.3087(3) 0.6324(6) 0.2111(3) 0.0410(10) Uani 1 1 d . . . C17 C 0.3986(3) 0.5405(5) 0.1869(3) 0.0442(10) Uani 1 1 d . . . H17 H 0.4000 0.4819 0.1334 0.053 Uiso 1 1 calc R . . C18 C 0.4854(4) 0.5378(6) 0.2435(3) 0.0445(11) Uani 1 1 d . . . H18 H 0.5455 0.4757 0.2281 0.053 Uiso 1 1 calc R . . O19 O 0.2177(2) 0.6429(4) 0.16162(19) 0.0530(9) Uani 1 1 d . . . C20 C 0.2141(4) 0.5552(8) 0.0788(3) 0.0690(15) Uani 1 1 d . . . H20A H 0.2676 0.5991 0.0393 0.103 Uiso 1 1 calc R . . H20B H 0.1446 0.5684 0.0523 0.103 Uiso 1 1 calc R . . H20C H 0.2277 0.4393 0.0891 0.103 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 C1 0.075(4) 0.094(5) 0.085(4) -0.003(4) -0.028(3) -0.030(3) O2 0.050(2) 0.069(2) 0.091(3) 0.005(2) -0.021(2) -0.0091(18) C3 0.041(3) 0.046(3) 0.061(3) 0.010(2) -0.008(2) -0.012(2) C4 0.052(3) 0.047(3) 0.039(2) -0.001(2) 0.002(2) -0.003(2) C5 0.039(2) 0.046(3) 0.049(3) 0.004(2) 0.003(2) 0.002(2) C6 0.038(2) 0.039(2) 0.042(3) 0.0022(18) 0.0036(18) -0.0031(19) C7 0.046(2) 0.048(3) 0.075(4) -0.018(2) 0.004(3) 0.004(2) C8 0.037(3) 0.060(3) 0.091(4) -0.014(3) -0.004(3) 0.013(2) C9 0.043(2) 0.041(2) 0.051(3) 0.000(2) -0.001(2) -0.0027(19) C10 0.066(3) 0.074(4) 0.045(3) 0.011(3) -0.001(2) -0.013(3) S11 0.0454(6) 0.0468(5) 0.0471(6) 0.0074(7) -0.0046(6) -0.0058(6) O12 0.059(2) 0.089(3) 0.0468(19) 0.0050(19) -0.0056(16) -0.0162(19) C13 0.034(2) 0.043(2) 0.041(2) 0.004(2) 0.0008(19) -0.003(2) C14 0.052(3) 0.043(3) 0.041(2) -0.009(2) 0.002(2) -0.005(2) C15 0.038(3) 0.046(3) 0.059(3) -0.007(2) 0.007(2) 0.004(2) C16 0.038(2) 0.043(3) 0.043(2) 0.000(2) 0.0000(19) -0.005(2) C17 0.040(2) 0.050(3) 0.043(2) -0.008(2) -0.002(2) -0.002(2) C18 0.040(2) 0.046(3) 0.047(3) -0.007(2) 0.004(2) 0.004(2) O19 0.0436(19) 0.063(2) 0.052(2) -0.0036(16) -0.0062(16) 0.0007(15) C20 0.065(4) 0.086(4) 0.056(3) -0.007(3) -0.016(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.434(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? O2 C3 1.355(5) . ? C3 C4 1.384(6) . ? C3 C8 1.387(7) . ? C4 C5 1.394(6) . ? C4 H4 0.9300 . ? C5 C6 1.375(5) . ? C5 H5 0.9300 . ? C6 C7 1.388(6) . ? C6 C9 1.503(6) . ? C7 C8 1.369(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.507(6) . ? C9 S11 1.853(4) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? S11 O12 1.479(3) . ? S11 C13 1.797(4) . ? C13 C18 1.375(6) . ? C13 C14 1.395(6) . ? C14 C15 1.371(6) . ? C14 H14 0.9300 . ? C15 C16 1.388(6) . ? C15 H15 0.9300 . ? C16 O19 1.360(5) . ? C16 C17 1.392(6) . ? C17 C18 1.376(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? O19 C20 1.429(6) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O2 C1 118.3(4) . . ? O2 C3 C4 124.9(4) . . ? O2 C3 C8 116.4(4) . . ? C4 C3 C8 118.6(4) . . ? C3 C4 C5 119.9(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 121.7(4) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 117.3(4) . . ? C5 C6 C9 120.8(4) . . ? C7 C6 C9 121.9(4) . . ? C8 C7 C6 121.9(4) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? C7 C8 C3 120.5(4) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? C6 C9 C10 114.4(4) . . ? C6 C9 S11 107.6(3) . . ? C10 C9 S11 110.2(3) . . ? C6 C9 H9 108.1 . . ? C10 C9 H9 108.1 . . ? S11 C9 H9 108.1 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O12 S11 C13 107.0(2) . . ? O12 S11 C9 106.2(2) . . ? C13 S11 C9 98.9(2) . . ? C18 C13 C14 120.2(4) . . ? C18 C13 S11 120.1(3) . . ? C14 C13 S11 119.7(3) . . ? C15 C14 C13 118.8(4) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 121.1(4) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? O19 C16 C15 115.7(4) . . ? O19 C16 C17 124.4(4) . . ? C15 C16 C17 119.9(4) . . ? C18 C17 C16 118.8(4) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C13 C18 C17 121.2(4) . . ? C13 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C16 O19 C20 118.0(4) . . ? O19 C20 H20A 109.5 . . ? O19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C1 O2 C3 C4 -13.0(7) . . . . ? C1 O2 C3 C8 169.6(5) . . . . ? O2 C3 C4 C5 -178.6(4) . . . . ? C8 C3 C4 C5 -1.3(7) . . . . ? C3 C4 C5 C6 0.0(6) . . . . ? C4 C5 C6 C7 1.2(6) . . . . ? C4 C5 C6 C9 -179.0(4) . . . . ? C5 C6 C7 C8 -1.2(7) . . . . ? C9 C6 C7 C8 179.0(4) . . . . ? C6 C7 C8 C3 -0.1(8) . . . . ? O2 C3 C8 C7 178.9(4) . . . . ? C4 C3 C8 C7 1.3(8) . . . . ? C5 C6 C9 C10 132.2(4) . . . . ? C7 C6 C9 C10 -48.0(6) . . . . ? C5 C6 C9 S11 -105.0(4) . . . . ? C7 C6 C9 S11 74.8(5) . . . . ? C6 C9 S11 O12 62.2(3) . . . . ? C10 C9 S11 O12 -172.4(3) . . . . ? C6 C9 S11 C13 172.9(3) . . . . ? C10 C9 S11 C13 -61.7(4) . . . . ? O12 S11 C13 C18 -152.0(3) . . . . ? C9 S11 C13 C18 97.9(4) . . . . ? O12 S11 C13 C14 27.3(4) . . . . ? C9 S11 C13 C14 -82.7(4) . . . . ? C18 C13 C14 C15 0.4(6) . . . . ? S11 C13 C14 C15 -178.9(3) . . . . ? C13 C14 C15 C16 -0.7(7) . . . . ? C14 C15 C16 O19 179.8(4) . . . . ? C14 C15 C16 C17 0.2(7) . . . . ? O19 C16 C17 C18 -179.1(4) . . . . ? C15 C16 C17 C18 0.5(6) . . . . ? C14 C13 C18 C17 0.3(6) . . . . ? S11 C13 C18 C17 179.6(4) . . . . ? C16 C17 C18 C13 -0.7(6) . . . . ? C15 C16 O19 C20 179.8(4) . . . . ? C17 C16 O19 C20 -0.6(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.210 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.056 #===END