# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Cosimo Cardellicchio' _publ_contact_author_address ; Chemistry CNR, Istituto di Chimica dei Composti OrganoMetallici c/o Dipartimento di Chimica via Orabona 4 Bari 70126 ITALY ; _publ_contact_author_email CARDELLICCHIO@BA.ICCOM.CNR.IT _publ_requested_category FA _publ_section_title ; Self--assemblies of chiral p--haloaryl sulfoxides through C---H...O short contacts and halogen involving interactions ; _publ_section_title_footnote ; Contribution No. ; loop_ _publ_author_name _publ_author_address 'Francesco Naso' ; Istituto di chimica dei composti organometallici - CNR Sezione di Bari and Dipartimento di Chimica, Universit\'a di Bari v. Orabona 4, 70126 Bari, Italy ; 'Cosimo Cardellicchio' ; Istituto di chimica dei composti organometallici - CNR Sezione di Bari v. Orabona 4, 70126 Bari, Italy ; 'Maria Annunziata M. Capozzi' ; Dipartimento di Scienze Agroambientali, Chimica e Difesa Vegetale Universit\'a degli Studi di Foggia v. Napoli 25, 71100 Foggia, Italy ; 'Francesco Capitelli' ; Istituto di cristallografia - CNR v. Amendola 122/o, 70126 Bari, Italy ; 'Valerio Bertolasi' ; Dipartimento di Chimica and Centro di Strutturistica Diffrattometrica Universit\'a di Ferrara v. Borsari 46, 44100 Ferrara, Italy ; # Attachment 'gm7.cif' data_gm7 _database_code_depnum_ccdc_archive 'CCDC 261489' _audit_creation_method SHELXL-97 _chemical_name_systematic 'p-bromophenyl methyl sulfoxide' _chemical_name_common 'p-bromophenyl methyl sulfoxide' _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 Br O S' _chemical_formula_sum 'C7 H7 Br O S' _chemical_formula_weight 219.10 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 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 8.9398(3) _cell_length_b 9.4924(3) _cell_length_c 10.0886(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 856.12(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12434 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 30.03 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 4.976 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3814 _exptl_absorpt_correction_T_max 0.4361 _exptl_absorpt_process_details ; R.H. Blessing, Acta Crystallogr., Sect. A, 1995, 51, 33-38. ; _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 Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10420 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 29.95 _reflns_number_total 2449 _reflns_number_gt 2088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0431P)^2^+0.1391P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 0.004(10) _refine_ls_number_reflns 2449 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.12597(4) 0.21272(3) 0.37778(3) 0.06703(12) Uani 1 1 d . . . S1 S 0.04744(8) 0.26957(8) -0.25271(8) 0.05705(16) Uani 1 1 d . . . C1 C 0.0714(3) 0.2541(3) -0.0772(3) 0.0486(5) Uani 1 1 d . . . C2 C 0.0267(4) 0.3636(3) 0.0047(3) 0.0562(6) Uani 1 1 d . . . C3 C 0.0439(4) 0.3508(3) 0.1394(3) 0.0545(6) Uani 1 1 d . . . C4 C 0.1049(3) 0.2285(3) 0.1916(3) 0.0498(5) Uani 1 1 d . . . C5 C 0.1496(4) 0.1180(3) 0.1108(3) 0.0567(7) Uani 1 1 d . . . C6 C 0.1313(4) 0.1313(3) -0.0244(3) 0.0560(6) Uani 1 1 d . . . C7 C 0.1900(6) 0.3980(4) -0.2807(4) 0.0744(9) Uani 1 1 d . . . O1 O 0.1016(4) 0.1348(3) -0.3124(2) 0.0815(8) Uani 1 1 d . . . H2 H -0.012(5) 0.448(5) -0.036(5) 0.080(12) Uiso 1 1 d . . . H3 H 0.022(4) 0.426(4) 0.198(4) 0.057(9) Uiso 1 1 d . . . H5 H 0.177(5) 0.043(5) 0.145(4) 0.075(12) Uiso 1 1 d . . . H6 H 0.146(5) 0.060(5) -0.069(5) 0.078(12) Uiso 1 1 d . . . H7A H 0.187(7) 0.412(6) -0.360(6) 0.101(17) Uiso 1 1 d . . . H7B H 0.156(6) 0.487(7) -0.219(6) 0.12(2) Uiso 1 1 d . . . H7C H 0.287(5) 0.358(5) -0.243(5) 0.091(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0939(2) 0.06375(17) 0.04348(14) 0.00291(12) 0.00052(15) -0.00305(16) S1 0.0676(4) 0.0597(4) 0.0439(3) -0.0047(3) -0.0041(3) 0.0002(3) C1 0.0516(12) 0.0483(13) 0.0460(12) -0.0025(9) 0.0017(10) 0.0013(10) C2 0.0705(17) 0.0472(13) 0.0508(14) -0.0049(12) -0.0033(13) 0.0114(12) C3 0.0693(16) 0.0465(12) 0.0476(14) -0.0053(10) 0.0024(12) 0.0072(12) C4 0.0569(14) 0.0494(12) 0.0433(11) 0.0005(9) 0.0010(10) -0.0049(11) C5 0.0723(18) 0.0485(13) 0.0492(14) 0.0029(11) 0.0017(13) 0.0085(12) C6 0.0732(17) 0.0449(13) 0.0501(13) -0.0032(10) 0.0088(14) 0.0081(14) C7 0.095(3) 0.069(2) 0.059(2) 0.0068(16) 0.0073(17) -0.0084(18) O1 0.133(2) 0.0592(12) 0.0520(12) -0.0136(9) 0.0039(14) -0.0014(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.893(3) . ? S1 O1 1.494(3) . ? S1 C7 1.786(4) . ? S1 C1 1.789(3) . ? C1 C2 1.386(4) . ? C1 C6 1.389(4) . ? C2 C3 1.374(4) . ? C2 H2 0.97(4) . ? C3 C4 1.386(4) . ? C3 H3 0.95(4) . ? C4 C5 1.388(4) . ? C5 C6 1.380(4) . ? C5 H5 0.83(5) . ? C6 H6 0.83(5) . ? C7 H7A 0.81(6) . ? C7 H7B 1.09(6) . ? C7 H7C 1.02(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 C7 106.8(2) . . ? O1 S1 C1 106.83(14) . . ? C7 S1 C1 97.27(16) . . ? C2 C1 C6 120.8(3) . . ? C2 C1 S1 119.6(2) . . ? C6 C1 S1 119.6(2) . . ? C3 C2 C1 119.4(3) . . ? C3 C2 H2 122(3) . . ? C1 C2 H2 118(3) . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 122(2) . . ? C4 C3 H3 118(2) . . ? C3 C4 C5 121.6(2) . . ? C3 C4 Br1 118.8(2) . . ? C5 C4 Br1 119.6(2) . . ? C6 C5 C4 118.5(3) . . ? C6 C5 H5 122(3) . . ? C4 C5 H5 119(3) . . ? C5 C6 C1 120.1(3) . . ? C5 C6 H6 117(3) . . ? C1 C6 H6 123(3) . . ? S1 C7 H7A 105(4) . . ? S1 C7 H7B 104(3) . . ? H7A C7 H7B 115(5) . . ? S1 C7 H7C 107(3) . . ? H7A C7 H7C 117(5) . . ? H7B C7 H7C 108(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.339 _refine_diff_density_min -0.657 _refine_diff_density_rms 0.064 # Attachment 'c219.cif' data_c219 _database_code_depnum_ccdc_archive 'CCDC 261491' _audit_creation_method SHELXL-97 _chemical_name_systematic 'p-bromophenyl i-propyl sulfoxide' _chemical_name_common 'p-bromophenyl i-propyl sulfoxide' _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 Br O S' _chemical_formula_sum 'C9 H11 Br O S' _chemical_formula_weight 247.15 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' Br Br -0.2901 2.4595 '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 P212121 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 9.4483(4) _cell_length_b 10.3257(5) _cell_length_c 10.9739(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1070.62(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13466 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 3.988 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2670 _exptl_absorpt_correction_T_max 0.6912 _exptl_absorpt_process_details ; R.H. Blessing, Acta Crystallogr., Sect. A, 1995, 51, 33-38. ; _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 Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12038 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 27.54 _reflns_number_total 2446 _reflns_number_gt 1572 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0864P)^2^+0.3221P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 2446 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1720 _refine_ls_wR_factor_gt 0.1546 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.66115(11) 0.23703(8) 0.61072(9) 0.1255(4) Uani 1 1 d . . . S1 S 0.75876(14) -0.37793(18) 0.57220(14) 0.0900(4) Uani 1 1 d . . . C1 C 0.7319(5) -0.2087(6) 0.5834(5) 0.0848(14) Uani 1 1 d . . . C2 C 0.8171(6) -0.1233(7) 0.5161(5) 0.0905(15) Uani 1 1 d . . . H2 H 0.8879 -0.1559 0.4659 0.109 Uiso 1 1 calc R . . C3 C 0.7963(6) 0.0091(8) 0.5240(6) 0.0957(18) Uani 1 1 d . . . H3 H 0.8526 0.0656 0.4793 0.115 Uiso 1 1 calc R . . C4 C 0.6900(7) 0.0568(6) 0.5997(6) 0.0927(16) Uani 1 1 d . . . C5 C 0.6046(6) -0.0290(7) 0.6636(7) 0.0952(18) Uani 1 1 d . . . H5 H 0.5316 0.0032 0.7117 0.114 Uiso 1 1 calc R . . C6 C 0.6250(6) -0.1567(7) 0.6574(6) 0.0879(16) Uani 1 1 d . . . H6 H 0.5676 -0.2118 0.7027 0.105 Uiso 1 1 calc R . . C7 C 0.8991(10) -0.3927(10) 0.6852(9) 0.136(3) Uani 1 1 d . . . H7 H 0.9753 -0.3337 0.6610 0.164 Uiso 1 1 calc R . . C8 C 0.8547(18) -0.3557(15) 0.8022(11) 0.205(7) Uani 1 1 d . . . H8A H 0.7918 -0.4203 0.8344 0.247 Uiso 1 1 calc R . . H8B H 0.8063 -0.2742 0.7976 0.247 Uiso 1 1 calc R . . H8C H 0.9356 -0.3476 0.8545 0.247 Uiso 1 1 calc R . . C9 C 0.9553(7) -0.5235(5) 0.6798(16) 0.280(12) Uani 1 1 d . . . H9A H 1.0392 -0.5289 0.7289 0.336 Uiso 1 1 calc R . . H9B H 0.9781 -0.5448 0.5970 0.336 Uiso 1 1 calc R . . H9C H 0.8858 -0.5833 0.7100 0.336 Uiso 1 1 calc R . . O1 O 0.6304(5) -0.4423(5) 0.6196(5) 0.1100(14) Uani 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1277(7) 0.1103(5) 0.1385(7) -0.0053(5) 0.0187(5) -0.0067(4) S1 0.0701(7) 0.1133(10) 0.0865(8) -0.0106(8) -0.0014(7) 0.0040(7) C1 0.060(2) 0.121(4) 0.073(3) 0.000(3) -0.001(2) -0.009(3) C2 0.067(3) 0.123(5) 0.082(3) -0.010(3) 0.005(3) 0.008(3) C3 0.073(3) 0.132(5) 0.082(4) 0.002(3) 0.013(3) -0.014(3) C4 0.091(3) 0.099(4) 0.088(4) -0.017(3) 0.000(3) -0.004(3) C5 0.071(3) 0.112(5) 0.102(4) -0.017(4) 0.014(3) -0.012(3) C6 0.070(3) 0.113(4) 0.081(3) -0.004(3) 0.011(3) -0.006(3) C7 0.136(6) 0.144(7) 0.129(6) -0.015(6) -0.055(5) 0.036(5) C8 0.224(14) 0.238(13) 0.154(10) -0.057(10) -0.067(10) 0.094(13) C9 0.36(2) 0.215(14) 0.270(19) -0.076(14) -0.17(2) 0.156(16) O1 0.092(3) 0.109(3) 0.129(4) 0.000(3) 0.004(3) -0.013(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 Br1 C4 1.885(6) . ? S1 O1 1.478(5) . ? S1 C1 1.770(7) . ? S1 C7 1.822(7) . ? C1 C6 1.403(8) . ? C1 C2 1.404(9) . ? C2 C3 1.384(11) . ? C2 H2 0.9300 . ? C3 C4 1.393(9) . ? C3 H3 0.9300 . ? C4 C5 1.388(10) . ? C5 C6 1.333(10) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.403(16) . ? C7 C9 1.452(11) . ? C7 H7 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 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 O1 S1 C1 107.6(3) . . ? O1 S1 C7 108.7(4) . . ? C1 S1 C7 98.0(4) . . ? C6 C1 C2 118.4(6) . . ? C6 C1 S1 121.5(5) . . ? C2 C1 S1 120.1(5) . . ? C3 C2 C1 120.4(5) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.3(6) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 119.6(6) . . ? C5 C4 Br1 120.9(5) . . ? C3 C4 Br1 119.4(5) . . ? C6 C5 C4 121.4(6) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 120.8(6) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C9 113.5(12) . . ? C8 C7 S1 112.5(8) . . ? C9 C7 S1 108.4(7) . . ? C8 C7 H7 107.4 . . ? C9 C7 H7 107.4 . . ? S1 C7 H7 107.4 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.574 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.060 data_c194 _database_code_depnum_ccdc_archive 'CCDC 261492' _audit_creation_method SHELXL-97 _chemical_name_systematic 'p-bromophenyl phenyl sulfoxide' _chemical_name_common 'p-bromophenyl phenyl sulfoxide' _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 Br O S' _chemical_formula_sum 'C12 H9 Br O S' _chemical_formula_weight 281.16 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 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 6.1391(2) _cell_length_b 7.7239(2) _cell_length_c 24.0213(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1139.04(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24488 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 3.760 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2655 _exptl_absorpt_correction_T_max 0.4656 _exptl_absorpt_process_details ; R.H. Blessing, Acta Crystallogr., Sect. A, 1995, 51, 33-38. ; _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 Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6909 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 30.08 _reflns_number_total 2994 _reflns_number_gt 2391 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0427P)^2^+0.2210P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 0.017(12) _refine_ls_number_reflns 2994 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.09770(8) 0.36162(5) 0.534247(17) 0.07586(16) Uani 1 1 d . . . S1 S 0.39583(17) 1.04528(10) 0.61951(4) 0.0588(2) Uani 1 1 d . . . C1 C 0.2624(5) 0.8532(4) 0.59436(12) 0.0482(6) Uani 1 1 d . . . C2 C 0.3679(6) 0.6942(4) 0.59699(15) 0.0547(7) Uani 1 1 d . . . C3 C 0.2652(6) 0.5481(4) 0.57798(15) 0.0577(8) Uani 1 1 d . . . C4 C 0.0558(6) 0.5631(4) 0.55674(12) 0.0498(7) Uani 1 1 d . . . C5 C -0.0484(6) 0.7212(4) 0.55283(14) 0.0529(7) Uani 1 1 d . . . C6 C 0.0562(5) 0.8677(4) 0.57190(13) 0.0519(6) Uani 1 1 d . . . C7 C 0.3097(5) 1.0277(4) 0.69075(14) 0.0510(6) Uani 1 1 d . . . C8 C 0.4473(7) 0.9541(5) 0.72933(18) 0.0712(10) Uani 1 1 d . . . C9 C 0.3810(13) 0.9495(7) 0.78415(19) 0.0923(16) Uani 1 1 d . . . C10 C 0.1847(12) 1.0184(7) 0.7995(2) 0.0925(16) Uani 1 1 d . . . C11 C 0.0504(9) 1.0933(8) 0.7609(2) 0.0889(16) Uani 1 1 d . . . C12 C 0.1116(8) 1.0971(6) 0.70568(18) 0.0710(10) Uani 1 1 d . . . O1 O 0.6332(5) 1.0098(4) 0.61878(14) 0.0857(9) Uani 1 1 d . . . H2 H 0.506(7) 0.701(5) 0.6160(17) 0.065(12) Uiso 1 1 d . . . H3 H 0.328(9) 0.437(7) 0.579(2) 0.100(17) Uiso 1 1 d . . . H5 H -0.186(8) 0.729(6) 0.5369(18) 0.076(13) Uiso 1 1 d . . . H6 H -0.010(6) 0.989(6) 0.5731(16) 0.065(11) Uiso 1 1 d . . . H8 H 0.594(9) 0.907(6) 0.7181(17) 0.072(12) Uiso 1 1 d . . . H9 H 0.476(12) 0.905(10) 0.803(3) 0.14(3) Uiso 1 1 d . . . H10 H 0.131(8) 1.008(5) 0.838(2) 0.079(13) Uiso 1 1 d . . . H11 H -0.098(14) 1.144(10) 0.771(3) 0.15(3) Uiso 1 1 d . . . H12 H 0.033(9) 1.141(7) 0.675(2) 0.098(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0910(3) 0.05405(18) 0.0826(3) -0.00669(16) -0.0163(2) -0.0061(2) S1 0.0593(4) 0.0497(4) 0.0675(5) 0.0003(3) 0.0101(5) -0.0067(4) C1 0.0495(15) 0.0466(13) 0.0487(14) 0.0032(12) 0.0071(12) 0.0014(13) C2 0.0479(18) 0.0538(15) 0.0624(18) 0.0022(13) -0.0044(14) 0.0104(13) C3 0.065(2) 0.0473(15) 0.0611(18) 0.0053(13) 0.0001(16) 0.0142(15) C4 0.060(2) 0.0485(13) 0.0410(13) 0.0018(11) 0.0051(13) 0.0025(13) C5 0.0479(17) 0.0540(16) 0.0569(17) 0.0033(13) 0.0003(13) 0.0065(13) C6 0.0501(17) 0.0477(13) 0.0578(16) 0.0016(13) 0.0054(12) 0.0075(13) C7 0.0509(15) 0.0445(13) 0.0578(17) -0.0055(12) -0.0019(13) -0.0012(12) C8 0.074(3) 0.067(2) 0.073(2) -0.0142(18) -0.0188(19) 0.0109(19) C9 0.137(5) 0.076(3) 0.064(2) -0.0064(19) -0.030(3) 0.007(3) C10 0.134(5) 0.088(3) 0.056(2) -0.016(2) 0.011(3) -0.023(3) C11 0.078(3) 0.114(4) 0.075(3) -0.028(3) 0.019(2) -0.008(3) C12 0.062(2) 0.082(2) 0.070(2) -0.0117(17) 0.000(2) 0.010(2) O1 0.0503(16) 0.0976(19) 0.109(2) -0.0199(17) 0.0271(15) -0.0158(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 Br1 C4 1.898(3) . ? S1 O1 1.483(3) . ? S1 C7 1.796(3) . ? S1 C1 1.799(3) . ? C1 C6 1.381(4) . ? C1 C2 1.390(4) . ? C2 C3 1.371(5) . ? C2 H2 0.96(4) . ? C3 C4 1.387(5) . ? C3 H3 0.94(6) . ? C4 C5 1.381(4) . ? C5 C6 1.380(5) . ? C5 H5 0.93(5) . ? C6 H6 1.02(4) . ? C7 C12 1.377(6) . ? C7 C8 1.377(5) . ? C8 C9 1.379(7) . ? C8 H8 1.01(5) . ? C9 C10 1.368(9) . ? C9 H9 0.81(8) . ? C10 C11 1.369(8) . ? C10 H10 0.99(5) . ? C11 C12 1.378(6) . ? C11 H11 1.02(8) . ? C12 H12 0.94(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 C7 106.66(18) . . ? O1 S1 C1 106.93(17) . . ? C7 S1 C1 97.08(14) . . ? C6 C1 C2 121.1(3) . . ? C6 C1 S1 118.8(2) . . ? C2 C1 S1 120.1(2) . . ? C3 C2 C1 119.8(3) . . ? C3 C2 H2 127(3) . . ? C1 C2 H2 113(3) . . ? C2 C3 C4 118.7(3) . . ? C2 C3 H3 123(3) . . ? C4 C3 H3 118(3) . . ? C5 C4 C3 121.9(3) . . ? C5 C4 Br1 118.4(3) . . ? C3 C4 Br1 119.8(2) . . ? C6 C5 C4 119.1(3) . . ? C6 C5 H5 120(3) . . ? C4 C5 H5 121(3) . . ? C5 C6 C1 119.3(3) . . ? C5 C6 H6 125(2) . . ? C1 C6 H6 116(2) . . ? C12 C7 C8 121.8(4) . . ? C12 C7 S1 118.6(3) . . ? C8 C7 S1 119.5(3) . . ? C7 C8 C9 118.2(5) . . ? C7 C8 H8 121(2) . . ? C9 C8 H8 121(2) . . ? C10 C9 C8 120.5(5) . . ? C10 C9 H9 131(6) . . ? C8 C9 H9 109(6) . . ? C9 C10 C11 120.8(5) . . ? C9 C10 H10 121(3) . . ? C11 C10 H10 118(3) . . ? C10 C11 C12 119.8(5) . . ? C10 C11 H11 123(5) . . ? C12 C11 H11 117(5) . . ? C7 C12 C11 118.9(4) . . ? C7 C12 H12 113(3) . . ? C11 C12 H12 128(4) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 30.08 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.321 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.073 # Attachment 'c378.cif' data_c378 _database_code_depnum_ccdc_archive 'CCDC 261493' _audit_creation_method SHELXL-97 _chemical_name_systematic 'chloromethyl p-chlorophenyl sulfoxide' _chemical_name_common 'chloromethyl p-chlorophenyl sulfoxide' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 Cl2 O S' _chemical_formula_sum 'C7 H6 Cl2 O S' _chemical_formula_weight 209.08 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' Cl Cl 0.1484 0.1585 '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 P212121 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 4.62620(10) _cell_length_b 9.2833(3) _cell_length_c 20.7170(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 889.72(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1529 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.901 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6715 _exptl_absorpt_correction_T_max 0.8474 _exptl_absorpt_process_details ; R.H. Blessing, Acta Crystallogr., Sect. A, 1995, 51, 33-38. ; _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 Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9817 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 30.07 _reflns_number_total 2597 _reflns_number_gt 2083 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0349P)^2^+0.1251P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(9) _refine_ls_number_reflns 2597 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.36610(12) 0.49032(7) 1.00448(3) 0.06842(17) Uani 1 1 d . . . Cl2 Cl 0.39716(13) 0.51335(7) 0.63446(3) 0.06978(17) Uani 1 1 d . . . S1 S 0.49679(10) 0.53733(5) 0.77217(2) 0.05345(14) Uani 1 1 d . . . O1 O 0.5798(4) 0.69126(18) 0.76519(8) 0.0762(5) Uani 1 1 d . . . C1 C 0.2477(4) 0.5245(2) 0.83844(9) 0.0451(4) Uani 1 1 d . . . C2 C 0.1510(5) 0.6481(2) 0.86838(12) 0.0549(5) Uani 1 1 d . . . C3 C -0.0394(5) 0.6369(2) 0.91985(11) 0.0569(5) Uani 1 1 d . . . C4 C -0.1267(4) 0.5031(2) 0.93996(9) 0.0490(4) Uani 1 1 d . . . C5 C -0.0285(5) 0.3800(2) 0.91070(11) 0.0547(5) Uani 1 1 d . . . C6 C 0.1626(5) 0.3900(2) 0.85953(11) 0.0523(5) Uani 1 1 d . . . C7 C 0.2260(4) 0.5044(3) 0.71097(10) 0.0524(4) Uani 1 1 d . . . H2 H 0.196(6) 0.743(3) 0.8527(12) 0.077(8) Uiso 1 1 d . . . H3 H -0.096(6) 0.716(3) 0.9408(12) 0.073(8) Uiso 1 1 d . . . H5 H -0.090(6) 0.301(3) 0.9233(12) 0.073(8) Uiso 1 1 d . . . H6 H 0.231(5) 0.304(3) 0.8379(11) 0.064(6) Uiso 1 1 d . . . H71 H 0.149(6) 0.416(3) 0.7196(12) 0.067(7) Uiso 1 1 d . . . H72 H 0.093(6) 0.572(3) 0.7128(12) 0.073(8) Uiso 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 Cl1 0.0710(3) 0.0843(4) 0.0499(3) -0.0003(3) 0.0095(2) -0.0017(3) Cl2 0.0806(4) 0.0763(4) 0.0524(3) 0.0061(3) 0.0063(2) 0.0059(3) S1 0.03876(19) 0.0651(3) 0.0565(3) 0.0089(2) 0.0001(2) -0.0055(2) O1 0.0778(11) 0.0778(10) 0.0729(10) 0.0087(9) 0.0037(9) -0.0373(9) C1 0.0420(8) 0.0453(9) 0.0479(10) 0.0027(8) -0.0032(7) -0.0051(8) C2 0.0589(12) 0.0411(10) 0.0648(13) 0.0058(9) -0.0008(11) -0.0044(8) C3 0.0651(14) 0.0450(10) 0.0605(13) -0.0069(9) 0.0012(11) 0.0032(10) C4 0.0477(9) 0.0564(11) 0.0428(9) 0.0017(8) -0.0033(7) 0.0004(10) C5 0.0658(13) 0.0414(9) 0.0568(12) 0.0048(8) 0.0053(11) -0.0081(10) C6 0.0601(12) 0.0396(9) 0.0571(12) 0.0002(8) 0.0042(10) -0.0004(8) C7 0.0451(9) 0.0579(12) 0.0543(11) 0.0030(10) 0.0001(8) 0.0034(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C4 1.7399(19) . ? Cl2 C7 1.774(2) . ? S1 O1 1.4867(17) . ? S1 C1 1.7964(19) . ? S1 C7 1.808(2) . ? C1 C2 1.379(3) . ? C1 C6 1.380(3) . ? C2 C3 1.387(3) . ? C2 H2 0.97(2) . ? C3 C4 1.371(3) . ? C3 H3 0.89(3) . ? C4 C5 1.372(3) . ? C5 C6 1.384(3) . ? C5 H5 0.83(3) . ? C6 H6 0.97(2) . ? C7 H71 0.91(3) . ? C7 H72 0.88(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 C1 107.67(10) . . ? O1 S1 C7 105.85(11) . . ? C1 S1 C7 94.60(8) . . ? C2 C1 C6 121.19(18) . . ? C2 C1 S1 119.79(15) . . ? C6 C1 S1 119.00(15) . . ? C1 C2 C3 119.31(18) . . ? C1 C2 H2 122.8(16) . . ? C3 C2 H2 117.6(16) . . ? C4 C3 C2 119.25(19) . . ? C4 C3 H3 120.7(18) . . ? C2 C3 H3 120.0(18) . . ? C3 C4 C5 121.55(18) . . ? C3 C4 Cl1 118.88(16) . . ? C5 C4 Cl1 119.56(15) . . ? C4 C5 C6 119.61(18) . . ? C4 C5 H5 118.9(19) . . ? C6 C5 H5 121.4(18) . . ? C1 C6 C5 119.07(19) . . ? C1 C6 H6 120.4(14) . . ? C5 C6 H6 120.5(14) . . ? Cl2 C7 S1 108.02(10) . . ? Cl2 C7 H71 113.1(16) . . ? S1 C7 H71 106.5(17) . . ? Cl2 C7 H72 108.6(16) . . ? S1 C7 H72 109.6(17) . . ? H71 C7 H72 111(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.07 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.252 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.040