Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Simon E. Lawrence' _publ_contact_author_address ;Department of Chemistry University College Cork Cork Ireland ; _publ_contact_author_email s.lawrence@ucc.ie _publ_contact_author_phone +353(21)4903143 _publ_contact_author_fax +353(21)4274097 loop_ _publ_author_name _publ_author_address K.N.Lehane ;Department of Chemistry Analytical and Biological Chemistry Research Facility University College Cork Cork Ireland ; E.J.A.Moynihan ;Department of Chemistry Analytical and Biological Chemistry Research Facility University College Cork Cork Ireland ; N.Brondel ;Department of Chemistry Analytical and Biological Chemistry Research Facility University College Cork Cork Ireland ; S.E.Lawrence ;Department of Chemistry Analytical and Biological Chemistry Research Facility University College Cork Cork Ireland ; A.R.Maguire ;Department of Chemistry Analytical and Biological Chemistry Research Facility University College Cork Cork Ireland ; _publ_section_title ; Impact of sulfur substituents on the C-H...O interaction of terminal alkynes in crystal engineering ; #===================================================================== data_Compound+/-1 _database_code_depnum_ccdc_archive 'CCDC 253938' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 O S' _chemical_formula_sum 'C9 H8 O S' _chemical_formula_weight 164.21 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 b c a' _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' '-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 14.745(2) _cell_length_b 5.7176(5) _cell_length_c 20.659(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1741.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 8.49 _cell_measurement_theta_max 15.51 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.309 _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 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1912 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.1096 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.45 _reflns_number_total 1615 _reflns_number_gt 741 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'PLATON (Spek, 1999)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1999)' _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^)+(0.0471P)^2^+0.5339P] 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 1615 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1854 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 S9 S 0.42495(8) 0.7448(2) 0.44491(5) 0.0593(4) Uani 1 1 d . . . O10 O 0.3883(2) 0.5034(5) 0.45396(13) 0.0717(10) Uani 1 1 d . . . C2 C 0.3650(3) 0.9919(9) 0.1659(2) 0.0579(13) Uani 1 1 d . . . C6 C 0.4005(3) 0.8279(7) 0.36280(19) 0.0449(11) Uani 1 1 d . . . C7 C 0.4342(3) 1.0366(8) 0.3385(2) 0.0539(12) Uani 1 1 d . . . H7 H 0.4654 1.1393 0.3654 0.065 Uiso 1 1 calc R . . C4 C 0.3412(3) 0.7303(9) 0.2588(2) 0.0527(11) Uani 1 1 d . . . H4 H 0.3094 0.6282 0.2321 0.063 Uiso 1 1 calc R . . C3 C 0.3754(3) 0.9391(8) 0.2339(2) 0.0489(11) Uani 1 1 d . . . C8 C 0.4209(3) 1.0903(8) 0.2744(2) 0.0559(12) Uani 1 1 d . . . H8 H 0.4430 1.2308 0.2581 0.067 Uiso 1 1 calc R . . C5 C 0.3544(3) 0.6755(7) 0.3229(2) 0.0520(12) Uani 1 1 d . . . H5 H 0.3323 0.5353 0.3393 0.062 Uiso 1 1 calc R . . C11 C 0.3472(3) 0.9398(7) 0.4834(2) 0.0718(15) Uani 1 1 d . . . H11A H 0.2879 0.9192 0.4652 0.108 Uiso 1 1 calc R . . H11B H 0.3667 1.0982 0.4768 0.108 Uiso 1 1 calc R . . H11C H 0.3453 0.9069 0.5289 0.108 Uiso 1 1 calc R . . C1 C 0.3601(4) 1.0361(9) 0.1111(2) 0.0810(17) Uani 1 1 d . . . H1 H 0.3562 1.0715 0.0673 0.097 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 S9 0.0757(8) 0.0510(7) 0.0512(6) 0.0033(7) -0.0034(7) 0.0027(8) O10 0.119(3) 0.0379(17) 0.0587(19) 0.0096(17) 0.0037(19) 0.0000(18) C2 0.053(3) 0.062(3) 0.058(3) 0.008(3) 0.002(3) 0.001(3) C6 0.049(3) 0.038(2) 0.047(2) 0.000(2) -0.001(2) 0.004(2) C7 0.068(3) 0.040(3) 0.053(3) -0.006(2) 0.000(3) -0.014(3) C4 0.052(3) 0.054(3) 0.052(3) -0.001(3) -0.003(2) -0.006(3) C3 0.046(3) 0.050(3) 0.051(3) 0.009(2) 0.004(2) 0.007(3) C8 0.060(3) 0.046(3) 0.061(3) 0.003(2) 0.010(3) -0.008(3) C5 0.060(3) 0.038(3) 0.059(3) 0.004(2) 0.003(2) -0.009(2) C11 0.106(4) 0.052(3) 0.058(3) -0.003(3) 0.018(3) 0.003(3) C1 0.102(4) 0.079(4) 0.061(3) 0.011(3) -0.002(3) -0.004(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 O10 1.494(3) . ? S9 C11 1.786(4) . ? S9 C6 1.798(4) . ? C2 C1 1.161(6) . ? C2 C3 1.444(6) . ? C6 C5 1.379(5) . ? C6 C7 1.386(5) . ? C7 C8 1.373(5) . ? C7 H7 0.9300 . ? C4 C5 1.374(6) . ? C4 C3 1.395(5) . ? C4 H4 0.9300 . ? C3 C8 1.378(5) . ? C8 H8 0.9300 . ? C5 H5 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C1 H1 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 O10 S9 C11 106.8(2) . . ? O10 S9 C6 106.84(19) . . ? C11 S9 C6 97.3(2) . . ? C1 C2 C3 177.4(6) . . ? C5 C6 C7 120.3(4) . . ? C5 C6 S9 119.7(3) . . ? C7 C6 S9 119.8(3) . . ? C8 C7 C6 119.3(4) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C5 C4 C3 120.0(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C8 C3 C4 119.2(4) . . ? C8 C3 C2 120.8(4) . . ? C4 C3 C2 120.0(4) . . ? C7 C8 C3 121.1(4) . . ? C7 C8 H8 119.5 . . ? C3 C8 H8 119.5 . . ? C4 C5 C6 120.1(4) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? S9 C11 H11A 109.5 . . ? S9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 C1 H1 180.0 . . ? 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 O10 S9 C6 C5 1.0(4) . . . . ? C11 S9 C6 C5 -109.1(4) . . . . ? O10 S9 C6 C7 -174.0(3) . . . . ? C11 S9 C6 C7 75.9(4) . . . . ? C5 C6 C7 C8 0.2(7) . . . . ? S9 C6 C7 C8 175.1(3) . . . . ? C5 C4 C3 C8 -1.2(6) . . . . ? C5 C4 C3 C2 177.2(4) . . . . ? C6 C7 C8 C3 -0.5(7) . . . . ? C4 C3 C8 C7 1.0(6) . . . . ? C2 C3 C8 C7 -177.4(4) . . . . ? C3 C4 C5 C6 0.8(6) . . . . ? C7 C6 C5 C4 -0.3(6) . . . . ? S9 C6 C5 C4 -175.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.45 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.264 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.057 #===================================================================== # END of data_Compound+/-1 CIF #===================================================================== #===================================================================== data_Compound(S)1 _database_code_depnum_ccdc_archive 'CCDC 253939' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 O S' _chemical_formula_sum 'C9 H8 O S' _chemical_formula_weight 164.21 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 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 5.9369(6) _cell_length_b 10.9023(10) _cell_length_c 13.2907(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 860.25(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 15.64 _cell_measurement_theta_max 17.79 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.313 _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 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1896 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.46 _reflns_number_total 1584 _reflns_number_gt 1467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'maXus (Gilmore et al, 1998)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1999)' _computing_publication_material 'SHELXL--97; PLATON' _refine_special_details ; The absolute configuration was checked by refinement in SHELXL-97 using TWIN and BASF to give 0.00001 for the correct enantiomer, with R1=0.029 and wR2=0.084. The incorrect enantiomer refined to R1=0.030 and wR2 0.087. 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^)+(0.0474P)^2^+0.1106P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _chemical_absolute_configuration ad _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 -0.04(11) _refine_ls_number_reflns 1584 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 0.1910(4) 0.53060(19) 0.32289(17) 0.0592(6) Uani 1 1 d . . . H1 H 0.2006 0.6151 0.3141 0.071 Uiso 1 1 calc R . . C2 C 0.1787(4) 0.42353(19) 0.33396(15) 0.0517(5) Uani 1 1 d . . . C3 C 0.1613(3) 0.29321(17) 0.35051(14) 0.0454(4) Uani 1 1 d . . . C4 C -0.0225(4) 0.24641(18) 0.40285(15) 0.0514(5) Uani 1 1 d . . . H4 H -0.1344 0.2992 0.4259 0.062 Uiso 1 1 calc R . . C5 C -0.0398(3) 0.12155(18) 0.42085(15) 0.0514(5) Uani 1 1 d . . . H5 H -0.1636 0.0901 0.4551 0.062 Uiso 1 1 calc R . . C6 C 0.1293(3) 0.04408(16) 0.38739(13) 0.0443(4) Uani 1 1 d . . . C7 C 0.3113(4) 0.08866(18) 0.33459(16) 0.0504(5) Uani 1 1 d . . . H7 H 0.4221 0.0354 0.3113 0.060 Uiso 1 1 calc R . . C8 C 0.3282(4) 0.21355(19) 0.31637(15) 0.0515(5) Uani 1 1 d . . . H8 H 0.4513 0.2443 0.2812 0.062 Uiso 1 1 calc R . . C11 C 0.1885(5) -0.1197(2) 0.53553(18) 0.0732(7) Uani 1 1 d . . . H11A H 0.1744 -0.2013 0.5619 0.110 Uiso 1 1 calc R . . H11B H 0.0965 -0.0647 0.5743 0.110 Uiso 1 1 calc R . . H11C H 0.3429 -0.0941 0.5394 0.110 Uiso 1 1 calc R . . O10 O 0.2752(4) -0.18106(13) 0.34909(15) 0.0851(6) Uani 1 1 d . . . S9 S 0.09836(10) -0.11764(4) 0.40750(4) 0.05619(18) 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 0.0746(15) 0.0376(11) 0.0655(13) 0.0035(10) 0.0028(11) 0.0001(10) C2 0.0631(13) 0.0439(11) 0.0482(10) 0.0012(8) -0.0018(10) 0.0008(9) C3 0.0584(12) 0.0354(9) 0.0425(9) -0.0001(7) -0.0033(9) -0.0009(8) C4 0.0538(11) 0.0408(10) 0.0596(11) -0.0040(10) 0.0079(10) 0.0052(8) C5 0.0531(11) 0.0416(10) 0.0594(11) 0.0012(10) 0.0117(9) -0.0032(9) C6 0.0547(11) 0.0314(8) 0.0468(9) -0.0014(7) 0.0002(9) -0.0026(8) C7 0.0556(11) 0.0384(10) 0.0571(11) -0.0047(8) 0.0111(10) 0.0028(8) C8 0.0567(12) 0.0432(10) 0.0547(11) 0.0007(9) 0.0124(10) -0.0050(9) C11 0.0904(17) 0.0554(13) 0.0739(15) 0.0147(12) -0.0036(13) 0.0115(13) O10 0.1226(16) 0.0367(8) 0.0961(13) -0.0117(8) 0.0322(12) 0.0084(10) S9 0.0673(3) 0.0322(2) 0.0690(3) -0.0007(2) 0.0022(3) -0.0064(2) _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 1.179(3) . ? C1 H1 0.9300 . ? C2 C3 1.442(3) . ? C3 C4 1.391(3) . ? C3 C8 1.393(3) . ? C4 C5 1.386(3) . ? C4 H4 0.9300 . ? C5 C6 1.385(3) . ? C5 H5 0.9300 . ? C6 C7 1.377(3) . ? C6 S9 1.7928(18) . ? C7 C8 1.387(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C11 S9 1.784(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? O10 S9 1.4773(19) . ? 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 H1 180.0 . . ? C1 C2 C3 178.3(2) . . ? C4 C3 C8 119.48(17) . . ? C4 C3 C2 119.60(18) . . ? C8 C3 C2 120.91(19) . . ? C5 C4 C3 120.29(17) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 119.33(17) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C7 C6 C5 121.14(17) . . ? C7 C6 S9 120.24(14) . . ? C5 C6 S9 118.52(15) . . ? C6 C7 C8 119.48(18) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C3 120.26(19) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? S9 C11 H11A 109.5 . . ? S9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O10 S9 C11 106.40(13) . . ? O10 S9 C6 108.00(9) . . ? C11 S9 C6 97.10(10) . . ? 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 C8 C3 C4 C5 0.0(3) . . . . ? C2 C3 C4 C5 -178.9(2) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C4 C5 C6 C7 -1.5(3) . . . . ? C4 C5 C6 S9 -177.76(16) . . . . ? C5 C6 C7 C8 1.3(3) . . . . ? S9 C6 C7 C8 177.52(17) . . . . ? C6 C7 C8 C3 -0.5(3) . . . . ? C4 C3 C8 C7 -0.1(3) . . . . ? C2 C3 C8 C7 178.7(2) . . . . ? C7 C6 S9 O10 -6.9(2) . . . . ? C5 C6 S9 O10 169.41(16) . . . . ? C7 C6 S9 C11 103.00(18) . . . . ? C5 C6 S9 C11 -80.73(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.155 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.031 #===================================================================== # END of data_Compound(S)1 CIF #===================================================================== #===================================================================== data_Compound2 _database_code_depnum_ccdc_archive 'CCDC 253940' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 O2 S' _chemical_formula_sum 'C9 H8 O2 S' _chemical_formula_weight 180.21 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 22.1885(13) _cell_length_b 5.6567(5) _cell_length_c 14.0833(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1767.6(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 15.83 _cell_measurement_theta_max 18.71 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.319 _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 'theta/2theta 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 2344 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 1 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.42 _reflns_number_total 1844 _reflns_number_gt 1547 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'maXus (Gilmore et al, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1999)' _computing_publication_material 'SHELXL--97; PLATON' _refine_special_details ; The absolute configuration was checked by refinement in SHELXL-97 using TWIN and BASF to give 0.28834 for the enantiomer used, with R1=0.0371 and wR2=0.1066. The other enantiomer refined to R1=0.0372 and wR2 0.1069. 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^)+(0.0520P)^2^+0.5622P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _chemical_absolute_configuration ad _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 0.10(13) _refine_ls_number_reflns 1844 _refine_ls_number_parameters 219 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 -0.0208(2) 0.9437(11) 0.8374(5) 0.0658(15) Uani 1 1 d . . . H1 H -0.0626 0.9416 0.8436 0.079 Uiso 1 1 calc R . . C2 C 0.0310(2) 0.9463(10) 0.8296(4) 0.0548(13) Uani 1 1 d . . . C3 C 0.09558(18) 0.9386(8) 0.8148(3) 0.0452(11) Uani 1 1 d . . . C4 C 0.12056(19) 0.7617(8) 0.7621(4) 0.0523(11) Uani 1 1 d . . . H4 H 0.0962 0.6428 0.7375 0.063 Uiso 1 1 calc R . . C5 C 0.18222(19) 0.7582(8) 0.7447(4) 0.0532(13) Uani 1 1 d . . . H5 H 0.1989 0.6364 0.7091 0.064 Uiso 1 1 calc R . . C6 C 0.21818(18) 0.9318(8) 0.7796(3) 0.0432(12) Uani 1 1 d . . . C7 C 0.1939(2) 1.1105(9) 0.8345(5) 0.0612(16) Uani 1 1 d . . . H7 H 0.2186 1.2288 0.8586 0.073 Uiso 1 1 calc R . . C8 C 0.1326(2) 1.1132(10) 0.8536(4) 0.0647(15) Uani 1 1 d . . . H8 H 0.1163 1.2306 0.8919 0.078 Uiso 1 1 calc R . . S9 S 0.29656(4) 0.9260(2) 0.75612(11) 0.0535(3) Uani 1 1 d . . . O10 O 0.31212(15) 0.6855(6) 0.7349(4) 0.0758(14) Uani 1 1 d . . . O11 O 0.32817(15) 1.0414(8) 0.8306(3) 0.0744(13) Uani 1 1 d . . . C12 C 0.3040(2) 1.0946(11) 0.6510(5) 0.0686(17) Uani 1 1 d . . . H12A H 0.2778 1.0317 0.6029 0.103 Uiso 1 1 calc R . . H12B H 0.3450 1.0876 0.6292 0.103 Uiso 1 1 calc R . . H12C H 0.2933 1.2560 0.6637 0.103 Uiso 1 1 calc R . . C21 C 0.7664(2) 0.4279(10) 0.4919(4) 0.0636(16) Uani 1 1 d . . . H21 H 0.8071 0.3916 0.4861 0.076 Uiso 1 1 calc R . . C22 C 0.71456(19) 0.4740(9) 0.4993(4) 0.0528(13) Uani 1 1 d . . . C23 C 0.65100(18) 0.5265(8) 0.5132(4) 0.0470(11) Uani 1 1 d . . . C24 C 0.6072(2) 0.3725(9) 0.4810(4) 0.0589(14) Uani 1 1 d . . . H24 H 0.6184 0.2380 0.4473 0.071 Uiso 1 1 calc R . . C25 C 0.5464(2) 0.4173(9) 0.4986(4) 0.0595(15) Uani 1 1 d . . . H25 H 0.5169 0.3137 0.4770 0.071 Uiso 1 1 calc R . . C26 C 0.53068(17) 0.6176(7) 0.5486(3) 0.0418(12) Uani 1 1 d . . . C27 C 0.57349(19) 0.7748(8) 0.5811(5) 0.0541(12) Uani 1 1 d . . . H27 H 0.5620 0.9096 0.6143 0.065 Uiso 1 1 calc R . . C28 C 0.63416(19) 0.7293(8) 0.5635(4) 0.0574(14) Uani 1 1 d . . . H28 H 0.6635 0.8337 0.5852 0.069 Uiso 1 1 calc R . . S29 S 0.45402(5) 0.6664(2) 0.57821(11) 0.0480(3) Uani 1 1 d . . . O30 O 0.41681(13) 0.5551(7) 0.5069(3) 0.0688(11) Uani 1 1 d . . . O31 O 0.44591(13) 0.9144(6) 0.5957(3) 0.0608(10) Uani 1 1 d . . . C32 C 0.4461(2) 0.5105(10) 0.6835(4) 0.0656(16) Uani 1 1 d . . . H32A H 0.4530 0.3454 0.6719 0.098 Uiso 1 1 calc R . . H32B H 0.4061 0.5324 0.7078 0.098 Uiso 1 1 calc R . . H32C H 0.4748 0.5674 0.7290 0.098 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 0.045(3) 0.082(4) 0.070(4) -0.016(3) -0.005(3) 0.010(3) C2 0.042(3) 0.067(3) 0.056(3) -0.006(3) -0.003(2) 0.006(2) C3 0.036(2) 0.052(3) 0.048(3) 0.000(3) -0.003(2) 0.007(2) C4 0.042(2) 0.052(3) 0.063(3) -0.013(3) -0.003(2) -0.004(2) C5 0.047(2) 0.046(3) 0.067(3) -0.015(3) 0.005(3) 0.0068(19) C6 0.036(2) 0.044(2) 0.049(3) -0.004(2) -0.008(2) 0.0058(19) C7 0.046(3) 0.050(3) 0.089(4) -0.025(3) -0.008(3) 0.005(2) C8 0.046(3) 0.068(3) 0.081(4) -0.026(3) -0.002(3) 0.012(2) S9 0.0332(5) 0.0501(6) 0.0772(9) -0.0033(8) -0.0056(6) 0.0087(5) O10 0.0497(18) 0.052(2) 0.125(4) -0.003(2) 0.004(2) 0.0148(15) O11 0.043(2) 0.088(3) 0.092(3) -0.010(3) -0.020(2) 0.0036(19) C12 0.044(2) 0.066(3) 0.096(5) 0.009(4) 0.005(3) 0.006(2) C21 0.037(2) 0.078(4) 0.076(4) 0.014(3) 0.005(3) 0.003(2) C22 0.044(3) 0.063(3) 0.052(3) 0.007(3) 0.001(2) -0.005(2) C23 0.033(2) 0.054(3) 0.053(3) 0.007(3) 0.001(2) -0.0003(19) C24 0.040(2) 0.056(3) 0.081(4) -0.019(3) 0.007(3) -0.002(2) C25 0.033(2) 0.055(3) 0.090(4) -0.023(3) -0.004(3) -0.004(2) C26 0.0280(18) 0.040(2) 0.057(3) -0.002(2) -0.0037(19) 0.0023(16) C27 0.043(2) 0.048(2) 0.071(3) -0.018(3) -0.001(3) -0.0005(18) C28 0.035(2) 0.056(3) 0.081(4) -0.009(3) -0.003(3) -0.0086(19) S29 0.0307(4) 0.0453(6) 0.0680(7) -0.0046(7) -0.0031(6) 0.0067(4) O30 0.0369(16) 0.077(2) 0.093(3) -0.017(2) -0.018(2) 0.0022(16) O31 0.0517(17) 0.0443(16) 0.086(3) -0.002(2) 0.0033(19) 0.0127(14) C32 0.043(3) 0.063(3) 0.091(5) 0.011(3) 0.018(3) 0.007(2) _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 1.156(6) . ? C1 H1 0.9300 . ? C2 C3 1.449(6) . ? C3 C4 1.364(6) . ? C3 C8 1.396(7) . ? C4 C5 1.390(6) . ? C4 H4 0.9300 . ? C5 C6 1.357(6) . ? C5 H5 0.9300 . ? C6 C7 1.382(7) . ? C6 S9 1.771(4) . ? C7 C8 1.386(7) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? S9 O11 1.420(4) . ? S9 O10 1.435(4) . ? S9 C12 1.769(7) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C21 C22 1.183(6) . ? C21 H21 0.9300 . ? C22 C23 1.455(6) . ? C23 C24 1.381(7) . ? C23 C28 1.399(7) . ? C24 C25 1.396(6) . ? C24 H24 0.9300 . ? C25 C26 1.379(6) . ? C25 H25 0.9300 . ? C26 C27 1.379(6) . ? C26 S29 1.773(4) . ? C27 C28 1.393(6) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? S29 O31 1.436(3) . ? S29 O30 1.445(4) . ? S29 C32 1.734(6) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 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 C2 C1 H1 180.0 . . ? C1 C2 C3 176.2(6) . . ? C4 C3 C8 119.5(4) . . ? C4 C3 C2 120.2(4) . . ? C8 C3 C2 120.3(4) . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.1(4) . . ? C5 C6 S9 119.8(4) . . ? C7 C6 S9 120.1(4) . . ? C6 C7 C8 119.9(5) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C3 119.6(5) . . ? C7 C8 H8 120.2 . . ? C3 C8 H8 120.2 . . ? O11 S9 O10 118.1(3) . . ? O11 S9 C12 108.9(3) . . ? O10 S9 C12 108.3(3) . . ? O11 S9 C6 109.8(2) . . ? O10 S9 C6 107.0(2) . . ? C12 S9 C6 103.8(2) . . ? S9 C12 H12A 109.5 . . ? S9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? S9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C22 C21 H21 180.0 . . ? C21 C22 C23 177.1(6) . . ? C24 C23 C28 119.7(4) . . ? C24 C23 C22 120.6(5) . . ? C28 C23 C22 119.6(4) . . ? C23 C24 C25 120.5(5) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C26 C25 C24 119.0(4) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C25 C26 C27 121.7(4) . . ? C25 C26 S29 119.4(3) . . ? C27 C26 S29 118.8(3) . . ? C26 C27 C28 119.2(4) . . ? C26 C27 H27 120.4 . . ? C28 C27 H27 120.4 . . ? C27 C28 C23 120.0(4) . . ? C27 C28 H28 120.0 . . ? C23 C28 H28 120.0 . . ? O31 S29 O30 118.3(2) . . ? O31 S29 C32 109.7(3) . . ? O30 S29 C32 108.4(3) . . ? O31 S29 C26 108.2(2) . . ? O30 S29 C26 108.5(2) . . ? C32 S29 C26 102.7(2) . . ? S29 C32 H32A 109.5 . . ? S29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? S29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 C8 C3 C4 C5 -1.7(8) . . . . ? C2 C3 C4 C5 177.6(5) . . . . ? C3 C4 C5 C6 -0.5(8) . . . . ? C4 C5 C6 C7 1.5(8) . . . . ? C4 C5 C6 S9 -179.5(4) . . . . ? C5 C6 C7 C8 -0.3(9) . . . . ? S9 C6 C7 C8 -179.3(5) . . . . ? C6 C7 C8 C3 -1.8(9) . . . . ? C4 C3 C8 C7 2.8(9) . . . . ? C2 C3 C8 C7 -176.5(5) . . . . ? C5 C6 S9 O11 -152.1(4) . . . . ? C7 C6 S9 O11 26.9(5) . . . . ? C5 C6 S9 O10 -22.8(5) . . . . ? C7 C6 S9 O10 156.2(5) . . . . ? C5 C6 S9 C12 91.6(5) . . . . ? C7 C6 S9 C12 -89.4(5) . . . . ? C28 C23 C24 C25 -0.3(9) . . . . ? C22 C23 C24 C25 176.8(5) . . . . ? C23 C24 C25 C26 0.0(9) . . . . ? C24 C25 C26 C27 0.4(9) . . . . ? C24 C25 C26 S29 -175.9(5) . . . . ? C25 C26 C27 C28 -0.5(9) . . . . ? S29 C26 C27 C28 175.8(5) . . . . ? C26 C27 C28 C23 0.2(9) . . . . ? C24 C23 C28 C27 0.2(9) . . . . ? C22 C23 C28 C27 -176.9(5) . . . . ? C25 C26 S29 O31 -158.3(4) . . . . ? C27 C26 S29 O31 25.4(5) . . . . ? C25 C26 S29 O30 -28.8(5) . . . . ? C27 C26 S29 O30 154.9(4) . . . . ? C25 C26 S29 C32 85.7(5) . . . . ? C27 C26 S29 C32 -90.6(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.229 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.048 #===================================================================== # END of data_Compound2 CIF #===================================================================== #===================================================================== data_Compound3 _database_code_depnum_ccdc_archive 'CCDC 253941' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 O2 S' _chemical_formula_sum 'C9 H8 O2 S' _chemical_formula_weight 180.21 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 6.0507(10) _cell_length_b 9.6244(11) _cell_length_c 7.9662(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.273(10) _cell_angle_gamma 90.00 _cell_volume 437.91(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.33 _cell_measurement_theta_max 15.31 _exptl_crystal_description shard _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 0.322 _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 60 _diffrn_standards_decay_% 50 _diffrn_reflns_number 926 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.42 _reflns_number_total 866 _reflns_number_gt 831 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'PLATON (Spek,2000)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek,2000)' _computing_publication_material 'SHELXL--97; PLATON' _refine_special_details ; The absolute configuration was checked by refinement in SHELXL-97 using TWIN and BASF to give 0.02740 for the enantiomer used, with R1=0.0562 and wR2=0.1476. The other enantiomer refined to R1=0.0563 and wR2 0.1480. 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^)+(0.1195P)^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 _chemical_absolute_configuration ad _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 0.0(2) _refine_ls_number_reflns 866 _refine_ls_number_parameters 110 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1476 _refine_ls_wR_factor_gt 0.1452 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.172 _refine_ls_shift/su_max 0.006 _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 0.8906(10) 0.4229(8) 0.2361(7) 0.0525(15) Uani 1 1 d . . . H1 H 0.9938 0.4878 0.2174 0.063 Uiso 1 1 calc R . . C2 C 0.7584(8) 0.3398(5) 0.2600(6) 0.0405(12) Uani 1 1 d . . . C3 C 0.6005(8) 0.2387(5) 0.2899(6) 0.0343(10) Uani 1 1 d . . . C4 C 0.3763(8) 0.2129(5) 0.1675(6) 0.0317(9) Uani 1 1 d . . . C5 C 0.2259(9) 0.1143(5) 0.2030(7) 0.0390(11) Uani 1 1 d . . . H5 H 0.0782 0.0982 0.1208 0.047 Uiso 1 1 calc R . . C6 C 0.3002(11) 0.0419(7) 0.3612(7) 0.0511(14) Uani 1 1 d . . . H6 H 0.2019 -0.0233 0.3862 0.061 Uiso 1 1 calc R . . C7 C 0.5211(13) 0.0659(8) 0.4833(8) 0.0520(15) Uani 1 1 d . . . H7 H 0.5694 0.0163 0.5894 0.062 Uiso 1 1 calc R . . C8 C 0.6697(9) 0.1620(7) 0.4497(7) 0.0479(13) Uani 1 1 d . . . H8 H 0.8171 0.1764 0.5332 0.057 Uiso 1 1 calc R . . S9 S 0.26886(16) 0.30877(11) -0.03385(13) 0.0343(4) Uani 1 1 d . . . O10 O 0.2927(7) 0.4561(5) 0.0094(6) 0.0521(10) Uani 1 1 d . . . O11 O 0.0367(7) 0.2578(5) -0.1290(5) 0.0491(10) Uani 1 1 d . . . C12 C 0.4533(11) 0.2641(7) -0.1551(7) 0.0481(13) Uani 1 1 d . . . H12A H 0.4641 0.1648 -0.1604 0.072 Uiso 1 1 calc R . . H12B H 0.6063 0.3023 -0.0979 0.072 Uiso 1 1 calc R . . H12C H 0.3904 0.3007 -0.2735 0.072 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 0.036(3) 0.062(4) 0.057(3) -0.003(3) 0.012(2) -0.012(3) C2 0.032(2) 0.047(3) 0.037(2) -0.007(2) 0.0029(17) 0.001(2) C3 0.029(2) 0.035(3) 0.038(2) -0.0066(18) 0.0085(18) 0.0007(18) C4 0.029(2) 0.034(2) 0.031(2) -0.0052(19) 0.0089(17) 0.0023(18) C5 0.039(2) 0.037(3) 0.041(2) -0.002(2) 0.0136(19) -0.006(2) C6 0.058(3) 0.049(3) 0.049(3) 0.003(3) 0.022(3) -0.009(3) C7 0.065(4) 0.056(3) 0.032(3) 0.005(2) 0.013(2) -0.005(3) C8 0.046(3) 0.057(3) 0.033(2) 0.000(2) 0.003(2) 0.005(3) S9 0.0287(6) 0.0366(6) 0.0343(6) 0.0025(5) 0.0059(4) 0.0031(5) O10 0.048(2) 0.044(2) 0.058(2) 0.002(2) 0.0085(17) 0.0079(18) O11 0.0322(18) 0.061(2) 0.0444(19) 0.0025(17) -0.0011(15) -0.0018(17) C12 0.052(3) 0.059(3) 0.038(2) 0.003(2) 0.020(2) 0.003(2) _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 1.190(8) . ? C1 H1 0.9300 . ? C2 C3 1.437(8) . ? C3 C4 1.407(6) . ? C3 C8 1.411(7) . ? C4 C5 1.407(7) . ? C4 S9 1.777(5) . ? C5 C6 1.380(7) . ? C5 H5 0.9300 . ? C6 C7 1.389(10) . ? C6 H6 0.9300 . ? C7 C8 1.376(9) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? S9 O11 1.444(4) . ? S9 O10 1.455(5) . ? S9 C12 1.754(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C2 C1 H1 180.0 . . ? C1 C2 C3 179.5(6) . . ? C4 C3 C8 117.7(5) . . ? C4 C3 C2 123.1(5) . . ? C8 C3 C2 119.2(4) . . ? C3 C4 C5 121.3(4) . . ? C3 C4 S9 121.0(4) . . ? C5 C4 S9 117.6(4) . . ? C6 C5 C4 119.1(5) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 120.3(5) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 121.0(5) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C3 120.6(5) . . ? C7 C8 H8 119.7 . . ? C3 C8 H8 119.7 . . ? O11 S9 O10 117.3(3) . . ? O11 S9 C12 108.3(3) . . ? O10 S9 C12 109.8(3) . . ? O11 S9 C4 107.5(2) . . ? O10 S9 C4 108.3(2) . . ? C12 S9 C4 105.1(3) . . ? S9 C12 H12A 109.5 . . ? S9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? S9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C8 C3 C4 C5 0.1(7) . . . . ? C2 C3 C4 C5 -179.1(5) . . . . ? C8 C3 C4 S9 177.6(4) . . . . ? C2 C3 C4 S9 -1.6(7) . . . . ? C3 C4 C5 C6 0.1(7) . . . . ? S9 C4 C5 C6 -177.5(4) . . . . ? C4 C5 C6 C7 -0.2(8) . . . . ? C5 C6 C7 C8 0.1(10) . . . . ? C6 C7 C8 C3 0.1(10) . . . . ? C4 C3 C8 C7 -0.2(8) . . . . ? C2 C3 C8 C7 179.1(5) . . . . ? C3 C4 S9 O11 180.0(4) . . . . ? C5 C4 S9 O11 -2.4(4) . . . . ? C3 C4 S9 O10 -52.5(4) . . . . ? C5 C4 S9 O10 125.1(4) . . . . ? C3 C4 S9 C12 64.8(5) . . . . ? C5 C4 S9 C12 -117.6(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.439 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.154 #===================================================================== # END of data_Compound3 CIF #===================================================================== #===================================================================== data_Compound4 _database_code_depnum_ccdc_archive 'CCDC 649227' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 O S' _chemical_formula_sum 'C10 H10 O S' _chemical_formula_weight 178.24 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 6.7881(4) _cell_length_b 7.9542(4) _cell_length_c 8.7386(4) _cell_angle_alpha 94.048(5) _cell_angle_beta 92.037(6) _cell_angle_gamma 95.872(7) _cell_volume 467.75(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 15.64 _cell_measurement_theta_max 18.83 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 0.293 _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 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1813 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.33 _reflns_number_total 1695 _reflns_number_gt 1384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'PLATON (Spek, 2000)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2000)' _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^)+(0.0601P)^2^+0.0947P] 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 0.073(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1695 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _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 S4 S 0.75783(9) 0.80716(7) 0.50969(6) 0.0533(2) Uani 1 1 d . . . O11 O 0.9522(2) 0.23438(19) 0.08972(18) 0.0546(4) Uani 1 1 d . . . C2 C 0.5525(3) 0.9178(3) 0.2647(3) 0.0477(5) Uani 1 1 d . . . C10 C 1.0124(3) 0.6338(3) 0.3339(2) 0.0485(5) Uani 1 1 d . . . H10 H 1.1097 0.7201 0.3691 0.058 Uiso 1 1 calc R . . C9 C 1.0636(3) 0.5013(3) 0.2367(2) 0.0490(5) Uani 1 1 d . . . H9 H 1.1934 0.4993 0.2066 0.059 Uiso 1 1 calc R . . C8 C 0.9190(3) 0.3717(3) 0.1847(2) 0.0432(5) Uani 1 1 d . . . C6 C 0.6763(3) 0.5096(3) 0.3265(2) 0.0473(5) Uani 1 1 d . . . H6 H 0.5461 0.5116 0.3558 0.057 Uiso 1 1 calc R . . C5 C 0.8197(3) 0.6408(3) 0.3801(2) 0.0433(5) Uani 1 1 d . . . C3 C 0.7141(3) 0.9690(3) 0.3784(3) 0.0510(5) Uani 1 1 d . . . H3A H 0.6845 1.0704 0.4378 0.061 Uiso 1 1 calc R . . H3B H 0.8347 0.9975 0.3253 0.061 Uiso 1 1 calc R . . C7 C 0.7261(3) 0.3769(3) 0.2302(3) 0.0491(5) Uani 1 1 d . . . H7 H 0.6293 0.2900 0.1955 0.059 Uiso 1 1 calc R . . C1 C 0.4236(4) 0.8764(3) 0.1735(3) 0.0594(6) Uani 1 1 d . . . H1 H 0.3210 0.8435 0.1008 0.071 Uiso 1 1 calc R . . C12 C 1.1490(4) 0.2222(3) 0.0406(3) 0.0599(6) Uani 1 1 d . . . H12A H 1.1907 0.3188 -0.0148 0.090 Uiso 1 1 calc R . . H12B H 1.1514 0.1205 -0.0251 0.090 Uiso 1 1 calc R . . H12C H 1.2370 0.2192 0.1285 0.090 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 S4 0.0726(4) 0.0511(4) 0.0360(3) -0.0015(2) 0.0003(2) 0.0101(3) O11 0.0578(10) 0.0488(9) 0.0563(9) -0.0073(7) 0.0031(7) 0.0087(7) C2 0.0522(13) 0.0429(12) 0.0489(12) 0.0016(9) 0.0036(10) 0.0096(9) C10 0.0478(12) 0.0472(12) 0.0481(12) -0.0001(9) -0.0051(9) -0.0024(9) C9 0.0410(11) 0.0548(13) 0.0512(13) 0.0038(10) 0.0007(9) 0.0047(9) C8 0.0505(12) 0.0400(11) 0.0392(11) 0.0039(8) -0.0012(9) 0.0063(9) C6 0.0442(12) 0.0488(12) 0.0488(12) 0.0040(9) 0.0038(9) 0.0038(9) C5 0.0528(13) 0.0419(11) 0.0356(10) 0.0051(8) -0.0019(9) 0.0068(9) C3 0.0574(14) 0.0404(11) 0.0537(13) -0.0012(9) -0.0018(10) 0.0029(9) C7 0.0490(12) 0.0428(11) 0.0528(12) -0.0006(9) 0.0002(10) -0.0043(9) C1 0.0625(15) 0.0596(15) 0.0552(14) -0.0001(11) -0.0062(12) 0.0072(12) C12 0.0656(15) 0.0623(15) 0.0550(14) 0.0008(11) 0.0082(11) 0.0221(12) _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 S4 C5 1.774(2) . ? S4 C3 1.823(2) . ? O11 C8 1.367(2) . ? O11 C12 1.428(3) . ? C2 C1 1.168(3) . ? C2 C3 1.460(3) . ? C10 C9 1.386(3) . ? C10 C5 1.388(3) . ? C10 H10 0.9300 . ? C9 C8 1.388(3) . ? C9 H9 0.9300 . ? C8 C7 1.386(3) . ? C6 C7 1.380(3) . ? C6 C5 1.396(3) . ? C6 H6 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C7 H7 0.9300 . ? C1 H1 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C5 S4 C3 101.12(10) . . ? C8 O11 C12 118.07(18) . . ? C1 C2 C3 179.8(3) . . ? C9 C10 C5 121.68(19) . . ? C9 C10 H10 119.2 . . ? C5 C10 H10 119.2 . . ? C10 C9 C8 119.3(2) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O11 C8 C7 115.85(18) . . ? O11 C8 C9 124.5(2) . . ? C7 C8 C9 119.6(2) . . ? C7 C6 C5 120.5(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C10 C5 C6 118.21(19) . . ? C10 C5 S4 121.26(16) . . ? C6 C5 S4 120.49(16) . . ? C2 C3 S4 113.82(15) . . ? C2 C3 H3A 108.8 . . ? S4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? S4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C6 C7 C8 120.69(19) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C2 C1 H1 180.0 . . ? O11 C12 H12A 109.5 . . ? O11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C5 C10 C9 C8 -0.4(3) . . . . ? C12 O11 C8 C7 -179.46(18) . . . . ? C12 O11 C8 C9 0.2(3) . . . . ? C10 C9 C8 O11 -179.47(19) . . . . ? C10 C9 C8 C7 0.2(3) . . . . ? C9 C10 C5 C6 0.3(3) . . . . ? C9 C10 C5 S4 177.83(17) . . . . ? C7 C6 C5 C10 0.0(3) . . . . ? C7 C6 C5 S4 -177.55(16) . . . . ? C3 S4 C5 C10 85.60(18) . . . . ? C3 S4 C5 C6 -96.91(18) . . . . ? C5 S4 C3 C2 61.19(18) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? O11 C8 C7 C6 179.79(19) . . . . ? C9 C8 C7 C6 0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.270 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.044 #===================================================================== # END of data_Compound4 CIF #===================================================================== #===================================================================== data_Compound5 _database_code_depnum_ccdc_archive 'CCDC 649228' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 O2 S' _chemical_formula_sum 'C10 H10 O2 S' _chemical_formula_weight 194.24 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/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 10.5942(7) _cell_length_b 7.9196(3) _cell_length_c 11.5721(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.590(4) _cell_angle_gamma 90.00 _cell_volume 960.03(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.74 _cell_measurement_theta_max 13.92 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.299 _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 0.71069 _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 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1875 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1777 _reflns_number_gt 1468 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'maXus (Gilmoreet al, 1998)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1999)' _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^)+(0.0563P)^2^+0.2901P] 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 1777 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 0.4596(3) 0.2051(5) 0.4993(2) 0.0847(9) Uani 1 1 d . . . H1 H 0.4266 0.1426 0.4336 0.102 Uiso 1 1 calc R . . C2 C 0.5010(2) 0.2837(3) 0.58182(19) 0.0547(5) Uani 1 1 d . . . C3 C 0.5496(2) 0.3767(3) 0.68617(19) 0.0526(5) Uani 1 1 d . . . H3A H 0.4789 0.4321 0.7152 0.063 Uiso 1 1 calc R . . H3B H 0.6070 0.4638 0.6663 0.063 Uiso 1 1 calc R . . S4 S 0.63426(4) 0.24523(7) 0.80233(4) 0.0507(2) Uani 1 1 d . . . O5 O 0.72740(15) 0.1428(2) 0.74783(16) 0.0725(5) Uani 1 1 d . . . C6 C 0.50723(17) 0.1050(2) 0.82385(15) 0.0411(4) Uani 1 1 d . . . C7 C 0.5174(2) -0.0648(3) 0.79934(17) 0.0506(5) Uani 1 1 d . . . H7 H 0.5873 -0.1045 0.7675 0.061 Uiso 1 1 calc R . . C8 C 0.4237(2) -0.1753(3) 0.8221(2) 0.0597(6) Uani 1 1 d . . . H8 H 0.4299 -0.2895 0.8051 0.072 Uiso 1 1 calc R . . C9 C 0.3208(2) -0.1163(3) 0.8701(2) 0.0591(6) Uani 1 1 d . . . H9 H 0.2574 -0.1912 0.8844 0.071 Uiso 1 1 calc R . . C10 C 0.31033(19) 0.0533(3) 0.89759(18) 0.0512(5) Uani 1 1 d . . . H10 H 0.2405 0.0918 0.9302 0.061 Uiso 1 1 calc R . . C11 C 0.40493(17) 0.1647(2) 0.87592(15) 0.0416(4) Uani 1 1 d . . . O12 O 0.40788(14) 0.33269(18) 0.90080(13) 0.0539(4) Uani 1 1 d . . . C13 C 0.3125(2) 0.3993(3) 0.9635(2) 0.0665(7) Uani 1 1 d . . . H13A H 0.2304 0.3919 0.9158 0.100 Uiso 1 1 calc R . . H13B H 0.3315 0.5154 0.9829 0.100 Uiso 1 1 calc R . . H13C H 0.3117 0.3355 1.0339 0.100 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 0.0827(19) 0.117(2) 0.0526(14) -0.0114(16) 0.0058(14) 0.0170(18) C2 0.0493(12) 0.0670(13) 0.0495(12) 0.0079(11) 0.0133(9) 0.0091(10) C3 0.0465(11) 0.0472(11) 0.0655(13) 0.0039(10) 0.0134(9) -0.0022(9) S4 0.0343(3) 0.0655(4) 0.0522(3) -0.0019(2) 0.0064(2) -0.0012(2) O5 0.0457(9) 0.0925(13) 0.0846(11) 0.0169(10) 0.0274(8) 0.0222(8) C6 0.0374(10) 0.0477(11) 0.0379(9) -0.0014(8) 0.0050(7) 0.0051(8) C7 0.0530(12) 0.0534(12) 0.0447(11) -0.0075(9) 0.0050(9) 0.0122(10) C8 0.0734(16) 0.0411(11) 0.0614(13) -0.0056(10) -0.0002(11) 0.0030(11) C9 0.0586(13) 0.0522(13) 0.0645(13) 0.0060(11) 0.0018(11) -0.0097(10) C10 0.0437(11) 0.0584(12) 0.0531(11) 0.0027(10) 0.0126(9) 0.0003(9) C11 0.0422(10) 0.0433(11) 0.0394(9) -0.0032(8) 0.0066(8) 0.0029(8) O12 0.0557(9) 0.0456(8) 0.0655(9) -0.0111(7) 0.0252(7) 0.0014(7) C13 0.0699(15) 0.0639(14) 0.0707(15) -0.0141(12) 0.0273(12) 0.0144(12) _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 1.169(4) . ? C1 H1 0.9300 . ? C2 C3 1.442(3) . ? C3 S4 1.826(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? S4 O5 1.4884(16) . ? S4 C6 1.791(2) . ? C6 C7 1.382(3) . ? C6 C11 1.399(2) . ? C7 C8 1.378(3) . ? C7 H7 0.9300 . ? C8 C9 1.376(3) . ? C8 H8 0.9300 . ? C9 C10 1.389(3) . ? C9 H9 0.9300 . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 O12 1.360(2) . ? O12 C13 1.430(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 C2 C1 H1 180.0 . . ? C1 C2 C3 177.9(3) . . ? C2 C3 S4 113.56(15) . . ? C2 C3 H3A 108.9 . . ? S4 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? S4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? O5 S4 C6 106.30(10) . . ? O5 S4 C3 106.42(10) . . ? C6 S4 C3 99.15(9) . . ? C7 C6 C11 120.42(19) . . ? C7 C6 S4 119.46(15) . . ? C11 C6 S4 119.81(14) . . ? C8 C7 C6 119.9(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 119.8(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 121.1(2) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 119.3(2) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? O12 C11 C10 125.33(17) . . ? O12 C11 C6 115.28(17) . . ? C10 C11 C6 119.39(18) . . ? C11 O12 C13 118.21(16) . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C2 C3 S4 O5 49.61(18) . . . . ? C2 C3 S4 C6 -60.50(16) . . . . ? O5 S4 C6 C7 5.31(19) . . . . ? C3 S4 C6 C7 115.51(17) . . . . ? O5 S4 C6 C11 179.00(15) . . . . ? C3 S4 C6 C11 -70.79(16) . . . . ? C11 C6 C7 C8 2.5(3) . . . . ? S4 C6 C7 C8 176.16(15) . . . . ? C6 C7 C8 C9 -0.5(3) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? C8 C9 C10 C11 0.2(3) . . . . ? C9 C10 C11 O12 -178.51(19) . . . . ? C9 C10 C11 C6 1.8(3) . . . . ? C7 C6 C11 O12 177.14(17) . . . . ? S4 C6 C11 O12 3.5(2) . . . . ? C7 C6 C11 C10 -3.1(3) . . . . ? S4 C6 C11 C10 -176.76(14) . . . . ? C10 C11 O12 C13 5.8(3) . . . . ? C6 C11 O12 C13 -174.49(18) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.220 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.050 #===================================================================== # END of data_Compound5 CIF #===================================================================== #===================================================================== data_Compound6 _database_code_depnum_ccdc_archive 'CCDC 649229' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 O3 S' _chemical_formula_sum 'C10 H10 O3 S' _chemical_formula_weight 210.24 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 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 7.9083(4) _cell_length_b 8.8890(4) _cell_length_c 14.4521(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1015.94(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.86 _cell_measurement_theta_max 14.21 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.296 _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 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '\w-2\q scans' _diffrn_measurement_method 'Nonius MACH3' _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 2570 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 25.47 _reflns_number_total 1894 _reflns_number_gt 1738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'maXus (Gilmore et al, 1998)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1999)' _computing_publication_material 'SHELXL--97; PLATON' _refine_special_details ; The absolute configuration was checked by refinement in SHELXL-97 using TWIN and BASF to give 0.00001 for the enantiomer used, with R1=0.029 and wR2=0.077. The other enantiomer refined to R1=0.030 and wR2 0.079. 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^)+(0.0286P)^2^+0.3126P] 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 0.0118(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 1894 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0766 _refine_ls_wR_factor_gt 0.0675 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 0.7063(4) 0.8837(3) -0.13385(16) 0.0560(6) Uani 1 1 d . . . H1 H 0.6343 0.8719 -0.1842 0.067 Uiso 1 1 calc R . . C2 C 0.7971(3) 0.8987(3) -0.07028(15) 0.0456(5) Uani 1 1 d . . . C3 C 0.9097(3) 0.9151(3) 0.00886(16) 0.0473(6) Uani 1 1 d . . . H3A H 0.9528 1.0172 0.0104 0.057 Uiso 1 1 calc R . . H3B H 1.0052 0.8477 0.0014 0.057 Uiso 1 1 calc R . . S4 S 0.80680(7) 0.87481(6) 0.11634(4) 0.03925(15) Uani 1 1 d . . . O5 O 0.7314(2) 0.72835(17) 0.10898(13) 0.0544(4) Uani 1 1 d . . . O6 O 0.9292(2) 0.9003(2) 0.18808(11) 0.0533(5) Uani 1 1 d . . . C7 C 0.6411(2) 1.0073(2) 0.12664(15) 0.0359(5) Uani 1 1 d . . . C8 C 0.4786(3) 0.9544(3) 0.13990(15) 0.0458(6) Uani 1 1 d . . . H8 H 0.4579 0.8514 0.1393 0.055 Uiso 1 1 calc R . . C9 C 0.3469(3) 1.0537(4) 0.15397(19) 0.0600(8) Uani 1 1 d . . . H9 H 0.2374 1.0182 0.1624 0.072 Uiso 1 1 calc R . . C10 C 0.3795(4) 1.2059(4) 0.1554(2) 0.0632(8) Uani 1 1 d . . . H10 H 0.2911 1.2728 0.1658 0.076 Uiso 1 1 calc R . . C11 C 0.5399(4) 1.2608(3) 0.14164(17) 0.0541(7) Uani 1 1 d . . . H11 H 0.5588 1.3641 0.1422 0.065 Uiso 1 1 calc R . . C12 C 0.6736(3) 1.1629(2) 0.12689(15) 0.0418(5) Uani 1 1 d . . . O13 O 0.8363(2) 1.20520(17) 0.11329(15) 0.0577(5) Uani 1 1 d . . . C14 C 0.8743(4) 1.3630(3) 0.1054(2) 0.0707(8) Uani 1 1 d . . . H14A H 0.8065 1.4065 0.0573 0.106 Uiso 1 1 calc R . . H14B H 0.9918 1.3755 0.0907 0.106 Uiso 1 1 calc R . . H14C H 0.8500 1.4121 0.1631 0.106 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 0.0631(15) 0.0583(14) 0.0466(14) -0.0013(12) 0.0002(13) 0.0125(15) C2 0.0534(13) 0.0403(12) 0.0430(12) -0.0009(10) 0.0095(12) 0.0093(13) C3 0.0440(14) 0.0527(14) 0.0453(13) -0.0047(11) 0.0095(11) 0.0029(11) S4 0.0406(3) 0.0379(3) 0.0393(3) -0.0015(3) 0.0002(3) 0.0023(3) O5 0.0677(11) 0.0351(8) 0.0603(10) 0.0013(8) 0.0003(10) -0.0013(8) O6 0.0490(10) 0.0638(11) 0.0471(9) -0.0048(8) -0.0069(8) 0.0069(9) C7 0.0365(10) 0.0386(11) 0.0325(11) -0.0049(10) -0.0008(10) 0.0005(9) C8 0.0433(12) 0.0522(13) 0.0420(14) -0.0002(10) 0.0025(10) -0.0078(11) C9 0.0375(13) 0.093(2) 0.0493(14) -0.0007(14) 0.0043(11) 0.0024(14) C10 0.0581(17) 0.079(2) 0.0521(15) -0.0032(15) 0.0023(13) 0.0271(16) C11 0.0712(17) 0.0446(13) 0.0465(15) -0.0044(11) -0.0052(13) 0.0140(13) C12 0.0474(13) 0.0399(12) 0.0382(11) -0.0034(10) -0.0026(12) -0.0004(10) O13 0.0532(10) 0.0384(8) 0.0814(12) -0.0031(10) 0.0017(11) -0.0136(8) C14 0.093(2) 0.0430(13) 0.0761(18) 0.0008(15) -0.0066(18) -0.0238(14) _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 1.174(3) . ? C1 H1 0.9300 . ? C2 C3 1.457(4) . ? C3 S4 1.790(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? S4 O5 1.4360(16) . ? S4 O6 1.4364(17) . ? S4 C7 1.768(2) . ? C7 C8 1.382(3) . ? C7 C12 1.407(3) . ? C8 C9 1.380(4) . ? C8 H8 0.9300 . ? C9 C10 1.378(4) . ? C9 H9 0.9300 . ? C10 C11 1.374(4) . ? C10 H10 0.9300 . ? C11 C12 1.386(3) . ? C11 H11 0.9300 . ? C12 O13 1.355(3) . ? O13 C14 1.439(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 C2 C1 H1 180.0 . . ? C1 C2 C3 179.2(3) . . ? C2 C3 S4 112.56(17) . . ? C2 C3 H3A 109.1 . . ? S4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? S4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? O5 S4 O6 118.46(11) . . ? O5 S4 C7 107.60(10) . . ? O6 S4 C7 109.46(10) . . ? O5 S4 C3 107.82(11) . . ? O6 S4 C3 106.78(11) . . ? C7 S4 C3 106.06(11) . . ? C8 C7 C12 120.3(2) . . ? C8 C7 S4 118.28(17) . . ? C12 C7 S4 121.34(16) . . ? C9 C8 C7 120.3(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 119.3(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C11 C10 C9 121.3(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? O13 C12 C11 124.9(2) . . ? O13 C12 C7 116.46(19) . . ? C11 C12 C7 118.6(2) . . ? C12 O13 C14 118.7(2) . . ? O13 C14 H14A 109.5 . . ? O13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C2 C3 S4 O5 53.7(2) . . . . ? C2 C3 S4 O6 -177.98(17) . . . . ? C2 C3 S4 C7 -61.3(2) . . . . ? O5 S4 C7 C8 9.4(2) . . . . ? O6 S4 C7 C8 -120.58(19) . . . . ? C3 S4 C7 C8 124.57(19) . . . . ? O5 S4 C7 C12 -174.29(19) . . . . ? O6 S4 C7 C12 55.7(2) . . . . ? C3 S4 C7 C12 -59.1(2) . . . . ? C12 C7 C8 C9 -0.3(4) . . . . ? S4 C7 C8 C9 176.02(19) . . . . ? C7 C8 C9 C10 -0.5(4) . . . . ? C8 C9 C10 C11 1.0(4) . . . . ? C9 C10 C11 C12 -0.7(4) . . . . ? C10 C11 C12 O13 -179.5(2) . . . . ? C10 C11 C12 C7 -0.2(4) . . . . ? C8 C7 C12 O13 -179.9(2) . . . . ? S4 C7 C12 O13 3.8(3) . . . . ? C8 C7 C12 C11 0.7(3) . . . . ? S4 C7 C12 C11 -175.56(18) . . . . ? C11 C12 O13 C14 -5.6(4) . . . . ? C7 C12 O13 C14 175.0(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.226 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.032 #===================================================================== # END of data_Compound6 CIF #===================================================================== #===================================================================== data_Compound7 _database_code_depnum_ccdc_archive 'CCDC 649230' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 F O2 S' _chemical_formula_sum 'C9 H7 F O2 S' _chemical_formula_weight 198.21 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' _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 7.3890(10) _cell_length_b 8.134(3) _cell_length_c 8.474(2) _cell_angle_alpha 109.23(2) _cell_angle_beta 98.60(2) _cell_angle_gamma 106.01(2) _cell_volume 445.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 5.85 _cell_measurement_theta_max 17.20 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.339 _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 60 _diffrn_standards_decay_% 20 _diffrn_reflns_number 1773 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.47 _reflns_number_total 1650 _reflns_number_gt 950 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius MACH3' _computing_cell_refinement 'Nonius MACH3' _computing_data_reduction 'PLATON (Spek,2000)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek,2000)' _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^)+(0.1639P)^2^+1.1172P] 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 1650 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1602 _refine_ls_R_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.3204 _refine_ls_wR_factor_gt 0.2340 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.5797(14) 0.7950(13) 0.5001(12) 0.073(3) Uani 1 1 d . . . H1 H 0.6555 0.8292 0.4302 0.087 Uiso 1 1 calc R . . C2 C 0.4848(11) 0.7521(11) 0.5878(11) 0.0566(19) Uani 1 1 d . . . C3 C 0.3638(12) 0.7081(11) 0.6996(10) 0.057(2) Uani 1 1 d . . . H3A H 0.4466 0.7299 0.8100 0.068 Uiso 1 1 calc R . . H3B H 0.2822 0.5778 0.6464 0.068 Uiso 1 1 calc R . . S4 S 0.2149(3) 0.8461(3) 0.7341(3) 0.0621(8) Uani 1 1 d . . . O5 O 0.0871(10) 0.8002(13) 0.5722(9) 0.105(3) Uani 1 1 d . . . O6 O 0.3431(11) 1.0343(9) 0.8313(10) 0.089(2) Uani 1 1 d . . . C7 C 0.0783(7) 0.7742(7) 0.8642(6) 0.0489(18) Uani 1 1 d G . . C8 C 0.1541(6) 0.8494(7) 1.0431(6) 0.062(2) Uani 1 1 d G . . H8 H 0.2789 0.9380 1.0934 0.074 Uiso 1 1 calc R . . C9 C 0.0434(8) 0.7923(8) 1.1468(5) 0.068(2) Uani 1 1 d G . . H9 H 0.0941 0.8427 1.2665 0.082 Uiso 1 1 calc R . . C10 C -0.1431(7) 0.6599(7) 1.0717(7) 0.0530(19) Uani 1 1 d G . . C11 C -0.2190(6) 0.5847(7) 0.8928(7) 0.069(2) Uani 1 1 d G . . H11 H -0.3438 0.4961 0.8425 0.083 Uiso 1 1 calc R . . C12 C -0.1083(7) 0.6418(8) 0.7891(5) 0.070(2) Uani 1 1 d G . . H12 H -0.1590 0.5914 0.6694 0.085 Uiso 1 1 calc R . . F13 F -0.2509(8) 0.6083(7) 1.1669(7) 0.0808(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 C1 0.080(6) 0.079(6) 0.073(6) 0.036(5) 0.047(5) 0.025(5) C2 0.054(4) 0.054(5) 0.059(5) 0.015(4) 0.023(4) 0.016(4) C3 0.068(5) 0.051(4) 0.056(5) 0.022(4) 0.028(4) 0.018(4) S4 0.0688(14) 0.0885(17) 0.0673(14) 0.0536(13) 0.0420(11) 0.0432(12) O5 0.087(5) 0.208(9) 0.083(5) 0.099(6) 0.049(4) 0.078(5) O6 0.109(5) 0.066(4) 0.140(6) 0.064(4) 0.085(5) 0.043(4) C7 0.055(4) 0.057(5) 0.053(4) 0.028(4) 0.033(4) 0.029(4) C8 0.056(5) 0.071(5) 0.048(5) 0.020(4) 0.019(4) 0.006(4) C9 0.082(6) 0.080(6) 0.052(5) 0.031(5) 0.035(5) 0.025(5) C10 0.055(4) 0.051(4) 0.075(5) 0.033(4) 0.039(4) 0.029(4) C11 0.046(4) 0.084(6) 0.074(6) 0.035(5) 0.016(4) 0.014(4) C12 0.055(5) 0.094(7) 0.051(5) 0.019(5) 0.011(4) 0.023(5) F13 0.084(3) 0.085(3) 0.103(4) 0.056(3) 0.063(3) 0.031(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 C2 1.165(11) . ? C1 H1 0.9300 . ? C2 C3 1.457(10) . ? C3 S4 1.766(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? S4 O5 1.413(7) . ? S4 O6 1.433(7) . ? S4 C7 1.735(4) . ? C7 C8 1.3900 . ? C7 C12 1.3900 . ? C8 C9 1.3900 . ? C8 H8 0.9300 . ? C9 C10 1.3900 . ? C9 H9 0.9300 . ? C10 F13 1.301(5) . ? C10 C11 1.3900 . ? C11 C12 1.3900 . ? C11 H11 0.9300 . ? C12 H12 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 C2 C1 H1 180.0 . . ? C1 C2 C3 176.8(9) . . ? C2 C3 S4 110.6(6) . . ? C2 C3 H3A 109.5 . . ? S4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? S4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? O5 S4 O6 119.5(5) . . ? O5 S4 C7 108.5(3) . . ? O6 S4 C7 108.6(3) . . ? O5 S4 C3 107.7(4) . . ? O6 S4 C3 106.8(4) . . ? C7 S4 C3 104.9(3) . . ? C8 C7 C12 120.0 . . ? C8 C7 S4 120.2(3) . . ? C12 C7 S4 119.8(3) . . ? C7 C8 C9 120.0 . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.0 . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? F13 C10 C9 120.9(5) . . ? F13 C10 C11 119.1(5) . . ? C9 C10 C11 120.0 . . ? C12 C11 C10 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 120.0 . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 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 C2 C3 S4 O5 63.4(7) . . . . ? C2 C3 S4 O6 -66.0(7) . . . . ? C2 C3 S4 C7 178.8(6) . . . . ? O5 S4 C7 C8 -160.3(5) . . . . ? O6 S4 C7 C8 -29.1(5) . . . . ? C3 S4 C7 C8 84.8(4) . . . . ? O5 S4 C7 C12 19.2(5) . . . . ? O6 S4 C7 C12 150.4(4) . . . . ? C3 S4 C7 C12 -95.7(4) . . . . ? C12 C7 C8 C9 0.0 . . . . ? S4 C7 C8 C9 179.5(4) . . . . ? C7 C8 C9 C10 0.0 . . . . ? C8 C9 C10 F13 -178.2(5) . . . . ? C8 C9 C10 C11 0.0 . . . . ? F13 C10 C11 C12 178.2(5) . . . . ? C9 C10 C11 C12 0.0 . . . . ? C10 C11 C12 C7 0.0 . . . . ? C8 C7 C12 C11 0.0 . . . . ? S4 C7 C12 C11 -179.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.538 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.112 #===================================================================== # END of data_Compound7 CIF #===================================================================== #===================================================================== data_Compound8 _database_code_depnum_ccdc_archive 'CCDC 649231' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 O3 S' _chemical_formula_sum 'C11 H12 O3 S' _chemical_formula_weight 224.27 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 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 6.5860(2) _cell_length_b 10.1867(3) _cell_length_c 16.9358(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1136.22(6) _cell_formula_units_Z 4 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 4794 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details ? _exptl_special_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) The 0 2 0 reflection has been omitted due to the beamstop. ; _diffrn_ambient_temperature 240(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 6747 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1514 _reflns_number_gt 1333 _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, 2000)' _computing_publication_material 'SHELXL-97; PLATON' _refine_special_details ; The absolute configuration was not determined reliably, 1056 Friedel pairs were averaged for the refinement. 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^)+(0.0375P)^2^+0.2329P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _chemical_absolute_configuration unk _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 0.47(11) _refine_ls_number_reflns 1514 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0753 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 1.1446(5) 0.7755(3) 0.03797(17) 0.0555(7) Uani 1 1 d . . . H1 H 1.1666 0.6884 0.0219 0.067 Uiso 1 1 calc R . . C2 C 1.1171(4) 0.8840(2) 0.05792(15) 0.0410(6) Uani 1 1 d . . . C3 C 1.0949(4) 1.0222(2) 0.07976(14) 0.0365(5) Uani 1 1 d . . . H3 H 1.1737 1.0382 0.1286 0.044 Uiso 1 1 calc R . . C4 C 1.1720(5) 1.1151(3) 0.01568(15) 0.0536(7) Uani 1 1 d . . . H4A H 1.1037 1.0958 -0.0337 0.080 Uiso 1 1 calc R . . H4B H 1.3172 1.1033 0.0091 0.080 Uiso 1 1 calc R . . H4C H 1.1442 1.2051 0.0310 0.080 Uiso 1 1 calc R . . S5 S 0.83153(9) 1.06115(5) 0.09878(3) 0.03469(16) Uani 1 1 d . . . O6 O 0.7140(3) 1.02601(17) 0.03031(10) 0.0448(5) Uani 1 1 d . . . O7 O 0.8267(3) 1.19572(15) 0.12411(10) 0.0459(4) Uani 1 1 d . . . C8 C 0.7518(4) 0.9602(2) 0.17743(13) 0.0366(5) Uani 1 1 d . . . C9 C 0.5789(4) 0.8833(3) 0.16656(17) 0.0471(6) Uani 1 1 d . . . H9 H 0.5154 0.8803 0.1169 0.057 Uiso 1 1 calc R . . C10 C 0.5010(5) 0.8116(3) 0.22882(18) 0.0610(8) Uani 1 1 d . . . H10 H 0.3830 0.7609 0.2221 0.073 Uiso 1 1 calc R . . C11 C 0.5977(5) 0.8151(3) 0.30067(19) 0.0636(9) Uani 1 1 d . . . H11 H 0.5449 0.7658 0.3429 0.076 Uiso 1 1 calc R . . C12 C 0.7698(5) 0.8890(3) 0.31240(16) 0.0578(8) Uani 1 1 d . . . H12 H 0.8336 0.8892 0.3620 0.069 Uiso 1 1 calc R . . C13 C 0.8496(4) 0.9634(2) 0.25094(14) 0.0429(6) Uani 1 1 d . . . O14 O 1.0160(3) 1.03992(19) 0.25668(10) 0.0550(5) Uani 1 1 d . . . C15 C 1.1284(6) 1.0381(3) 0.32946(15) 0.0659(9) Uani 1 1 d . . . H15A H 1.1717 0.9490 0.3408 0.099 Uiso 1 1 calc R . . H15B H 1.0427 1.0696 0.3720 0.099 Uiso 1 1 calc R . . H15C H 1.2465 1.0944 0.3247 0.099 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 0.0449(16) 0.0448(14) 0.0769(19) -0.0113(13) 0.0046(16) 0.0050(13) C2 0.0318(13) 0.0450(13) 0.0461(13) -0.0013(11) 0.0035(11) 0.0033(10) C3 0.0312(11) 0.0390(12) 0.0393(13) -0.0017(9) 0.0021(10) 0.0013(10) C4 0.0539(16) 0.0533(14) 0.0535(15) 0.0061(12) 0.0145(17) -0.0022(15) S5 0.0330(3) 0.0346(3) 0.0364(3) 0.0026(2) 0.0009(3) 0.0050(2) O6 0.0413(11) 0.0522(10) 0.0409(8) 0.0045(7) -0.0069(8) 0.0021(8) O7 0.0516(10) 0.0330(8) 0.0530(10) 0.0004(7) 0.0049(10) 0.0089(8) C8 0.0320(11) 0.0388(12) 0.0390(12) 0.0042(10) 0.0061(10) 0.0039(11) C9 0.0326(13) 0.0526(14) 0.0561(15) 0.0026(13) 0.0030(13) 0.0002(12) C10 0.0395(15) 0.0649(18) 0.079(2) 0.0107(17) 0.0147(17) -0.0066(15) C11 0.059(2) 0.0677(19) 0.0638(18) 0.0213(16) 0.0196(17) -0.0027(17) C12 0.0620(19) 0.0657(17) 0.0459(15) 0.0154(13) 0.0078(15) 0.0047(15) C13 0.0429(14) 0.0442(13) 0.0416(12) 0.0057(10) 0.0049(12) 0.0028(13) O14 0.0597(12) 0.0652(12) 0.0400(9) 0.0096(9) -0.0095(9) -0.0153(12) C15 0.078(2) 0.0752(19) 0.0446(15) -0.0005(14) -0.0172(16) -0.0101(19) _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 1.170(3) . ? C1 H1 0.9400 . ? C2 C3 1.462(3) . ? C3 C4 1.527(3) . ? C3 S5 1.809(2) . ? C3 H3 0.9900 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 H4C 0.9700 . ? S5 O7 1.4368(16) . ? S5 O6 1.4393(17) . ? S5 C8 1.763(2) . ? C8 C9 1.394(3) . ? C8 C13 1.402(3) . ? C9 C10 1.382(4) . ? C9 H9 0.9400 . ? C10 C11 1.374(5) . ? C10 H10 0.9400 . ? C11 C12 1.375(5) . ? C11 H11 0.9400 . ? C12 C13 1.391(4) . ? C12 H12 0.9400 . ? C13 O14 1.348(3) . ? O14 C15 1.438(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? 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 H1 180.0 . . ? C1 C2 C3 176.1(3) . . ? C2 C3 C4 112.5(2) . . ? C2 C3 S5 110.61(18) . . ? C4 C3 S5 108.04(18) . . ? C2 C3 H3 108.5 . . ? C4 C3 H3 108.5 . . ? S5 C3 H3 108.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O7 S5 O6 117.77(11) . . ? O7 S5 C8 108.94(11) . . ? O6 S5 C8 107.68(11) . . ? O7 S5 C3 106.49(12) . . ? O6 S5 C3 108.52(11) . . ? C8 S5 C3 106.98(11) . . ? C9 C8 C13 120.4(2) . . ? C9 C8 S5 118.10(19) . . ? C13 C8 S5 121.36(19) . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 119.3(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 121.6(3) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C11 C12 C13 120.1(3) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? O14 C13 C12 124.6(3) . . ? O14 C13 C8 116.8(2) . . ? C12 C13 C8 118.6(3) . . ? C13 O14 C15 118.2(2) . . ? O14 C15 H15A 109.5 . . ? O14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C2 C3 S5 O7 176.68(17) . . . . ? C4 C3 S5 O7 -59.72(18) . . . . ? C2 C3 S5 O6 -55.6(2) . . . . ? C4 C3 S5 O6 67.98(18) . . . . ? C2 C3 S5 C8 60.3(2) . . . . ? C4 C3 S5 C8 -176.10(17) . . . . ? O7 S5 C8 C9 119.0(2) . . . . ? O6 S5 C8 C9 -9.8(2) . . . . ? C3 S5 C8 C9 -126.3(2) . . . . ? O7 S5 C8 C13 -56.4(2) . . . . ? O6 S5 C8 C13 174.8(2) . . . . ? C3 S5 C8 C13 58.3(2) . . . . ? C13 C8 C9 C10 1.1(4) . . . . ? S5 C8 C9 C10 -174.4(2) . . . . ? C8 C9 C10 C11 -1.2(4) . . . . ? C9 C10 C11 C12 0.4(5) . . . . ? C10 C11 C12 C13 0.5(5) . . . . ? C11 C12 C13 O14 179.3(3) . . . . ? C11 C12 C13 C8 -0.5(4) . . . . ? C9 C8 C13 O14 179.9(2) . . . . ? S5 C8 C13 O14 -4.8(3) . . . . ? C9 C8 C13 C12 -0.3(4) . . . . ? S5 C8 C13 C12 175.1(2) . . . . ? C12 C13 O14 C15 4.6(4) . . . . ? C8 C13 O14 C15 -175.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.165 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.055 #===================================================================== # END of data_Compound8 CIF #=====================================================================