# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address R.Sekiya ; Department of Life Sciences, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan ; R.Kuroda ; Department of Life Sciences, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan ; _publ_contact_author_address ; Department of Life Sciences, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan ; _publ_contact_author_email ckuroda@mail.ecc.u-tokyo.ac.jp _publ_contact_author_fax +81-3-5454-6600 _publ_contact_author_phone +81-3-5454-6600 _publ_contact_author_name 'Kuroda, Reiko' #===END # Attachment '- compound_1.cif' data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 679703' _audit_creation_date 2010-11-17T16:36:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-(2-methylphenylthio)-3-methyl-2-cyclohexenone ; _chemical_formula_moiety 'C14 H16 O S' _chemical_formula_sum 'C14 H16 O S' _chemical_formula_weight 232.33 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9230(16) _cell_length_b 10.418(2) _cell_length_c 15.473(3) _cell_angle_alpha 91.07(3) _cell_angle_beta 102.32(3) _cell_angle_gamma 104.43(3) _cell_volume 1204.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 5421 _cell_measurement_theta_min 1.35 _cell_measuremenT_theta_max 27.82 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.244 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS ver 2.03' _exptl_absorpt_correction_T_min 0.9087 _exptl_absorpt_correction_T_max 0.9528 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 103(2) _diffrn_radiation_probe X-ray _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_unetI/netI 0.0451 _diffrn_reflns_number 7394 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 27.82 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.91 _reflns_number_total 5205 _reflns_number_gt 4521 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0604P)^2^+0.3422P] 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_number_reflns 5205 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.403 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 S2 S 0.83123(5) 0.31551(4) 0.13737(3) 0.01980(12) Uani 1 1 d . . . S1 S 0.40524(6) 0.28817(4) 0.44759(3) 0.02092(12) Uani 1 1 d . . . O1 O 0.79452(17) 0.32100(12) 0.46265(8) 0.0271(3) Uani 1 1 d . . . C1 C 0.3789(2) 0.14203(16) 0.37991(11) 0.0186(3) Uani 1 1 d . . . C22 C 0.8190(2) 0.14324(15) 0.13852(11) 0.0185(3) Uani 1 1 d . . . C13 C 0.4986(2) 0.51359(16) 0.36209(10) 0.0168(3) Uani 1 1 d . . . C5 C 0.2794(2) -0.09614(17) 0.36010(13) 0.0258(4) Uani 1 1 d . . . H5 H 0.2318 -0.1792 0.3815 0.031 Uiso 1 1 calc R . . C8 C 0.5521(2) 0.41196(15) 0.40265(10) 0.0170(3) Uani 1 1 d . . . C9 C 0.7412(2) 0.40391(16) 0.41787(11) 0.0191(3) Uani 1 1 d . . . C12 C 0.6277(2) 0.62690(16) 0.33258(11) 0.0209(3) Uani 1 1 d . . . H12A H 0.5991 0.711 0.3467 0.025 Uiso 1 1 calc R . . H12B H 0.6106 0.6154 0.2674 0.025 Uiso 1 1 calc R . . C15 C 1.0961(2) 0.52275(16) 0.10943(10) 0.0184(3) Uani 1 1 d . . . C17 C 1.1749(2) 0.31187(16) 0.12353(11) 0.0203(3) Uani 1 1 d . . . H17 H 1.1441 0.2201 0.1334 0.024 Uiso 1 1 calc R . . C2 C 0.4201(2) 0.14432(17) 0.29675(11) 0.0218(3) Uani 1 1 d . . . H2 H 0.4686 0.2269 0.275 0.026 Uiso 1 1 calc R . . O2 O 0.7513(2) 0.11940(14) -0.01876(9) 0.0406(4) Uani 1 1 d . . . C21 C 0.9674(2) 0.60660(16) 0.11293(11) 0.0223(4) Uani 1 1 d . . . H21A H 1.0196 0.6972 0.0989 0.033 Uiso 1 1 calc R . . H21B H 0.944 0.6087 0.1726 0.033 Uiso 1 1 calc R . . H21C H 0.855 0.5684 0.0696 0.033 Uiso 1 1 calc R . . C27 C 0.8461(2) 0.08402(16) 0.21567(11) 0.0195(3) Uani 1 1 d . . . C6 C 0.3049(2) 0.02029(16) 0.41247(12) 0.0206(3) Uani 1 1 d . . . C4 C 0.3216(2) -0.09391(18) 0.27747(13) 0.0285(4) Uani 1 1 d . . . H4 H 0.3032 -0.1747 0.243 0.034 Uiso 1 1 calc R . . C16 C 1.0501(2) 0.38550(16) 0.12170(10) 0.0173(3) Uani 1 1 d . . . C19 C 1.3894(2) 0.50583(18) 0.09623(11) 0.0242(4) Uani 1 1 d . . . H19 H 1.5043 0.5469 0.0864 0.029 Uiso 1 1 calc R . . C11 C 0.8237(2) 0.63854(17) 0.37540(12) 0.0229(4) Uani 1 1 d . . . H11A H 0.9013 0.6999 0.3433 0.027 Uiso 1 1 calc R . . H11B H 0.8509 0.6755 0.4377 0.027 Uiso 1 1 calc R . . C20 C 1.2657(2) 0.57985(17) 0.09576(11) 0.0223(4) Uani 1 1 d . . . H20 H 1.2978 0.6716 0.0859 0.027 Uiso 1 1 calc R . . C10 C 0.8617(2) 0.50262(17) 0.37287(12) 0.0236(4) Uani 1 1 d . . . H10A H 0.8441 0.4694 0.3104 0.028 Uiso 1 1 calc R . . H10B H 0.988 0.511 0.4027 0.028 Uiso 1 1 calc R . . C26 C 0.8172(2) -0.06413(17) 0.21674(13) 0.0268(4) Uani 1 1 d . . . H26A H 0.7576 -0.0952 0.2654 0.032 Uiso 1 1 calc R . . H26B H 0.935 -0.0848 0.2296 0.032 Uiso 1 1 calc R . . C7 C 0.2536(2) 0.01489(18) 0.50086(12) 0.0257(4) Uani 1 1 d . . . H7A H 0.2049 -0.0779 0.5118 0.039 Uiso 1 1 calc R . . H7B H 0.163 0.0641 0.5004 0.039 Uiso 1 1 calc R . . H7C H 0.3595 0.0549 0.5478 0.039 Uiso 1 1 calc R . . C23 C 0.7768(3) 0.06714(18) 0.05109(12) 0.0263(4) Uani 1 1 d . . . C18 C 1.3449(2) 0.37206(17) 0.11102(11) 0.0234(4) Uani 1 1 d . . . H18 H 1.4301 0.3216 0.1126 0.028 Uiso 1 1 calc R . . C14 C 0.3098(2) 0.52461(17) 0.34308(12) 0.0222(4) Uani 1 1 d . . . H14A H 0.2297 0.4386 0.3492 0.033 Uiso 1 1 calc R . . H14B H 0.2773 0.5506 0.2825 0.033 Uiso 1 1 calc R . . H14C H 0.2988 0.5919 0.3852 0.033 Uiso 1 1 calc R . . C28 C 0.9070(2) 0.15710(19) 0.30505(12) 0.0272(4) Uani 1 1 d . . . H28A H 0.9572 0.2516 0.299 0.041 Uiso 1 1 calc R . . H28B H 0.9988 0.1211 0.3418 0.041 Uiso 1 1 calc R . . H28C H 0.8052 0.1467 0.3332 0.041 Uiso 1 1 calc R . . C3 C 0.3907(2) 0.02677(18) 0.24541(12) 0.0270(4) Uani 1 1 d . . . H3 H 0.4179 0.029 0.1885 0.032 Uiso 1 1 calc R . . C25 C 0.7054(3) -0.14003(18) 0.13058(14) 0.0329(4) Uani 1 1 d . . . H25A H 0.7112 -0.2338 0.1312 0.039 Uiso 1 1 calc R . . H25B H 0.579 -0.1385 0.1244 0.039 Uiso 1 1 calc R . . C24 C 0.7738(3) -0.07802(19) 0.05282(14) 0.0370(5) Uani 1 1 d . . . H24A H 0.8963 -0.0876 0.0564 0.044 Uiso 1 1 calc R . . H24B H 0.6964 -0.1262 -0.0031 0.044 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 S2 0.0212(2) 0.0149(2) 0.0251(2) 0.00166(16) 0.00862(16) 0.00495(15) S1 0.0255(2) 0.0171(2) 0.0204(2) -0.00013(15) 0.01100(16) 0.00101(16) O1 0.0284(6) 0.0264(7) 0.0278(7) 0.0030(5) 0.0031(5) 0.0121(5) C1 0.0163(7) 0.0178(8) 0.0212(8) -0.0006(6) 0.0026(6) 0.0050(6) C22 0.0200(8) 0.0139(7) 0.0232(8) 0.0017(6) 0.0086(6) 0.0040(6) C13 0.0165(7) 0.0187(8) 0.0137(7) -0.0035(6) 0.0036(6) 0.0023(6) C5 0.0177(8) 0.0167(8) 0.0406(10) 0.0026(7) 0.0029(7) 0.0035(6) C8 0.0182(7) 0.0155(7) 0.0167(7) -0.0010(6) 0.0064(6) 0.0014(6) C9 0.0213(8) 0.0186(8) 0.0170(7) -0.0026(6) 0.0037(6) 0.0053(6) C12 0.0231(8) 0.0188(8) 0.0205(8) 0.0030(6) 0.0062(7) 0.0037(6) C15 0.0248(8) 0.0150(8) 0.0127(7) 0.0001(6) 0.0017(6) 0.0026(6) C17 0.0228(8) 0.0164(8) 0.0209(8) 0.0011(6) 0.0038(7) 0.0047(6) C2 0.0217(8) 0.0214(8) 0.0221(8) 0.0004(7) 0.0046(7) 0.0055(7) O2 0.0685(10) 0.0312(8) 0.0218(7) 0.0013(6) 0.0082(7) 0.0143(7) C21 0.0285(9) 0.0168(8) 0.0206(8) 0.0006(6) 0.0035(7) 0.0060(7) C27 0.0147(7) 0.0198(8) 0.0259(8) 0.0042(7) 0.0078(6) 0.0048(6) C6 0.0132(7) 0.0198(8) 0.0278(9) 0.0034(7) 0.0018(6) 0.0043(6) C4 0.0212(8) 0.0224(9) 0.0386(11) -0.0099(8) 0.0011(8) 0.0055(7) C16 0.0192(7) 0.0168(8) 0.0145(7) 0.0009(6) 0.0038(6) 0.0020(6) C19 0.0210(8) 0.0268(9) 0.0203(8) -0.0019(7) 0.0059(7) -0.0025(7) C11 0.0198(8) 0.0211(8) 0.0260(9) 0.0015(7) 0.0080(7) -0.0003(7) C20 0.0282(9) 0.0172(8) 0.0167(8) -0.0001(6) 0.0037(7) -0.0016(7) C10 0.0189(8) 0.0274(9) 0.0257(9) -0.0011(7) 0.0096(7) 0.0045(7) C26 0.0281(9) 0.0206(9) 0.0353(10) 0.0107(7) 0.0111(8) 0.0084(7) C7 0.0237(8) 0.0230(9) 0.0307(9) 0.0086(7) 0.0073(7) 0.0052(7) C23 0.0338(9) 0.0212(9) 0.0250(9) 0.0004(7) 0.0088(8) 0.0074(7) C18 0.0219(8) 0.0246(9) 0.0227(9) -0.0022(7) 0.0031(7) 0.0061(7) C14 0.0192(8) 0.0225(9) 0.0242(8) -0.0002(7) 0.0028(7) 0.0060(7) C28 0.0272(9) 0.0329(10) 0.0215(9) 0.0045(7) 0.0030(7) 0.0096(8) C3 0.0239(8) 0.0299(10) 0.0260(9) -0.0060(7) 0.0047(7) 0.0063(7) C25 0.0329(10) 0.0155(8) 0.0492(12) 0.0024(8) 0.0106(9) 0.0033(7) C24 0.0586(14) 0.0191(9) 0.0345(11) -0.0037(8) 0.0130(10) 0.0107(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S2 C22 1.7737(17) . ? S2 C16 1.7759(17) . ? S1 C8 1.7695(17) . ? S1 C1 1.7740(17) . ? O1 C9 1.218(2) . ? C1 C2 1.392(2) . ? C1 C6 1.409(2) . ? C22 C27 1.355(2) . ? C22 C23 1.485(2) . ? C13 C8 1.352(2) . ? C13 C14 1.496(2) . ? C13 C12 1.505(2) . ? C5 C4 1.388(3) . ? C5 C6 1.393(3) . ? C5 H5 0.95 . ? C8 C9 1.490(2) . ? C9 C10 1.508(2) . ? C12 C11 1.526(2) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C15 C20 1.390(2) . ? C15 C16 1.412(2) . ? C15 C21 1.507(2) . ? C17 C16 1.391(2) . ? C17 C18 1.393(2) . ? C17 H17 0.95 . ? C2 C3 1.388(2) . ? C2 H2 0.95 . ? O2 C23 1.220(2) . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C27 C28 1.489(2) . ? C27 C26 1.504(2) . ? C6 C7 1.506(2) . ? C4 C3 1.387(3) . ? C4 H4 0.95 . ? C19 C18 1.386(2) . ? C19 C20 1.389(3) . ? C19 H19 0.95 . ? C11 C10 1.521(2) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C20 H20 0.95 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C26 C25 1.515(3) . ? C26 H26A 0.99 . ? C26 H26B 0.99 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C23 C24 1.507(3) . ? C18 H18 0.95 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? C3 H3 0.95 . ? C25 C24 1.514(3) . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? 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 C22 S2 C16 102.99(8) . . ? C8 S1 C1 103.54(8) . . ? C2 C1 C6 120.30(15) . . ? C2 C1 S1 123.07(13) . . ? C6 C1 S1 116.56(13) . . ? C27 C22 C23 121.70(15) . . ? C27 C22 S2 121.42(13) . . ? C23 C22 S2 116.88(13) . . ? C8 C13 C14 123.84(15) . . ? C8 C13 C12 121.93(15) . . ? C14 C13 C12 114.22(14) . . ? C4 C5 C6 121.72(17) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C13 C8 C9 121.69(15) . . ? C13 C8 S1 121.79(13) . . ? C9 C8 S1 116.37(12) . . ? O1 C9 C8 122.00(16) . . ? O1 C9 C10 121.99(15) . . ? C8 C9 C10 116.00(14) . . ? C13 C12 C11 114.00(14) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.6 . . ? C20 C15 C16 118.17(15) . . ? C20 C15 C21 120.46(15) . . ? C16 C15 C21 121.35(15) . . ? C16 C17 C18 120.33(16) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C3 C2 C1 120.47(17) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C22 C27 C28 124.09(16) . . ? C22 C27 C26 121.43(16) . . ? C28 C27 C26 114.48(15) . . ? C5 C6 C1 117.96(16) . . ? C5 C6 C7 120.50(16) . . ? C1 C6 C7 121.54(15) . . ? C3 C4 C5 119.70(16) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C17 C16 C15 120.28(15) . . ? C17 C16 S2 122.79(13) . . ? C15 C16 S2 116.91(13) . . ? C18 C19 C20 119.93(16) . . ? C18 C19 H19 120 . . ? C20 C19 H19 120 . . ? C10 C11 C12 110.09(14) . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.2 . . ? C19 C20 C15 121.49(16) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? C9 C10 C11 111.64(14) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108 . . ? C27 C26 C25 113.69(15) . . ? C27 C26 H26A 108.8 . . ? C25 C26 H26A 108.8 . . ? C27 C26 H26B 108.8 . . ? C25 C26 H26B 108.8 . . ? H26A C26 H26B 107.7 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C23 C22 122.20(16) . . ? O2 C23 C24 121.30(17) . . ? C22 C23 C24 116.45(16) . . ? C19 C18 C17 119.75(16) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C4 C3 C2 119.83(17) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C24 C25 C26 110.09(16) . . ? C24 C25 H25A 109.6 . . ? C26 C25 H25A 109.6 . . ? C24 C25 H25B 109.6 . . ? C26 C25 H25B 109.6 . . ? H25A C25 H25B 108.2 . . ? C23 C24 C25 112.07(16) . . ? C23 C24 H24A 109.2 . . ? C25 C24 H24A 109.2 . . ? C23 C24 H24B 109.2 . . ? C25 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? _chemical_name_common 2-(2-methylphenylthio)-3-methyl-2-cyclohexenone #===END # Attachment '- compound_2.cif' data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 679704' _audit_creation_date 2010-11-17T15:49:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-(2-chlorophenylthio)-3-methyl-2-cyclohexenone ; _chemical_formula_moiety 'C13 H13 Cl O S' _chemical_formula_sum 'C13 H13 Cl O S' _chemical_formula_weight 252.75 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.596(3) _cell_length_b 14.935(3) _cell_length_c 20.531(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4782.2(17) _cell_formula_units_Z 16 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6231 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 27.87 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.468 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS ver 2.03' _exptl_absorpt_correction_T_min 0.8348 _exptl_absorpt_correction_T_max 0.9121 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 103(2) _diffrn_radiation_probe X-ray _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_unetI/netI 0.0269 _diffrn_reflns_number 39673 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.87 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 5630 _reflns_number_gt 4938 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0468P)^2^+2.4637P] 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_number_reflns 5630 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.093 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.452 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 S2 S 0.16420(3) 0.68806(3) 0.138309(19) 0.02226(10) Uani 1 1 d . . . Cl2 Cl 0.18378(3) 0.67946(3) 0.28879(2) 0.03247(12) Uani 1 1 d . . . O2 O 0.14900(8) 0.50816(8) 0.08086(6) 0.0294(3) Uani 1 1 d . . . C19 C 0.07450(10) 0.65943(10) 0.18676(7) 0.0180(3) Uani 1 1 d . . . C14 C 0.08359(10) 0.65800(10) 0.25452(8) 0.0208(3) Uani 1 1 d . . . C22 C 0.08389(11) 0.70094(12) -0.05455(8) 0.0271(4) Uani 1 1 d . . . H22A H 0.1341 0.7127 -0.0828 0.032 Uiso 1 1 calc R . . H22B H 0.0368 0.7405 -0.0692 0.032 Uiso 1 1 calc R . . C20 C 0.12881(10) 0.66146(11) 0.05821(7) 0.0186(3) Uani 1 1 d . . . C25 C 0.13338(10) 0.56499(11) 0.04020(7) 0.0196(3) Uani 1 1 d . . . C21 C 0.10705(10) 0.72514(11) 0.01475(8) 0.0220(3) Uani 1 1 d . . . C18 C -0.00665(10) 0.64134(11) 0.16148(8) 0.0224(3) Uani 1 1 d . . . H18 H -0.0152 0.6419 0.1157 0.027 Uiso 1 1 calc R . . C15 C 0.01557(11) 0.63997(11) 0.29551(8) 0.0246(3) Uani 1 1 d . . . H15 H 0.0237 0.6397 0.3414 0.03 Uiso 1 1 calc R . . C17 C -0.07498(11) 0.62258(12) 0.20242(8) 0.0264(4) Uani 1 1 d . . . H17 H -0.1297 0.6097 0.1843 0.032 Uiso 1 1 calc R . . C16 C -0.06439(11) 0.62237(11) 0.26948(8) 0.0265(4) Uani 1 1 d . . . H16 H -0.1117 0.6103 0.2973 0.032 Uiso 1 1 calc R . . C23 C 0.05646(11) 0.60455(12) -0.06353(8) 0.0272(4) Uani 1 1 d . . . H23A H 0.0536 0.5904 -0.1106 0.033 Uiso 1 1 calc R . . H23B H -0.0014 0.5959 -0.0448 0.033 Uiso 1 1 calc R . . C24 C 0.11939(11) 0.54202(11) -0.03038(8) 0.0238(3) Uani 1 1 d . . . H24A H 0.0977 0.4799 -0.0336 0.029 Uiso 1 1 calc R . . H24B H 0.175 0.5447 -0.0536 0.029 Uiso 1 1 calc R . . C26 C 0.10345(12) 0.82317(12) 0.02959(10) 0.0326(4) Uani 1 1 d . . . H26A H 0.0435 0.8423 0.0323 0.049 Uiso 1 1 calc R . . H26B H 0.1325 0.8566 -0.0051 0.049 Uiso 1 1 calc R . . H26C H 0.1321 0.8348 0.0712 0.049 Uiso 1 1 calc R . . S1 S 0.13356(3) 0.46377(3) 0.40318(2) 0.03123(12) Uani 1 1 d . . . Cl1 Cl 0.10750(4) 0.45008(3) 0.55259(2) 0.03834(13) Uani 1 1 d . . . C6 C 0.15039(10) 0.35997(11) 0.44268(8) 0.0199(3) Uani 1 1 d . . . C8 C 0.23428(11) 0.44326(11) 0.29250(8) 0.0236(3) Uani 1 1 d . . . C7 C 0.14614(10) 0.43529(10) 0.31959(7) 0.0198(3) Uani 1 1 d . . . C3 C 0.17356(10) 0.19909(11) 0.51102(8) 0.0230(3) Uani 1 1 d . . . H3 H 0.181 0.1444 0.534 0.028 Uiso 1 1 calc R . . C1 C 0.13849(10) 0.35495(11) 0.50994(8) 0.0205(3) Uani 1 1 d . . . C5 C 0.17537(10) 0.28215(11) 0.41037(8) 0.0215(3) Uani 1 1 d . . . H5 H 0.1845 0.2836 0.3646 0.026 Uiso 1 1 calc R . . C12 C 0.07893(10) 0.41084(10) 0.28221(8) 0.0215(3) Uani 1 1 d . . . C11 C 0.09020(11) 0.38965(11) 0.21129(8) 0.0247(3) Uani 1 1 d . . . H11A H 0.0723 0.4422 0.1853 0.03 Uiso 1 1 calc R . . H11B H 0.0519 0.3392 0.1997 0.03 Uiso 1 1 calc R . . O1 O 0.29613(9) 0.45550(10) 0.32714(7) 0.0403(3) Uani 1 1 d . . . C4 C 0.18710(11) 0.20249(11) 0.44426(8) 0.0235(3) Uani 1 1 d . . . H4 H 0.2045 0.1501 0.4216 0.028 Uiso 1 1 calc R . . C10 C 0.18105(11) 0.36526(12) 0.19323(8) 0.0271(4) Uani 1 1 d . . . H10A H 0.1865 0.3618 0.1453 0.033 Uiso 1 1 calc R . . H10B H 0.1956 0.3059 0.2116 0.033 Uiso 1 1 calc R . . C2 C 0.14916(10) 0.27587(11) 0.54386(8) 0.0216(3) Uani 1 1 d . . . H2 H 0.1398 0.2742 0.5896 0.026 Uiso 1 1 calc R . . C9 C 0.24222(11) 0.43511(13) 0.21951(8) 0.0287(4) Uani 1 1 d . . . H9A H 0.3018 0.4184 0.2081 0.034 Uiso 1 1 calc R . . H9B H 0.2296 0.4937 0.1991 0.034 Uiso 1 1 calc R . . C13 C -0.01108(12) 0.40185(13) 0.30657(11) 0.0380(5) Uani 1 1 d . . . H13A H -0.0236 0.3386 0.3151 0.057 Uiso 1 1 calc R . . H13B H -0.0509 0.4248 0.2737 0.057 Uiso 1 1 calc R . . H13C H -0.0176 0.4363 0.3469 0.057 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 S2 0.01992(19) 0.0284(2) 0.0184(2) -0.00532(15) 0.00082(14) -0.00657(15) Cl2 0.0312(2) 0.0449(3) 0.0213(2) -0.00334(17) -0.00660(16) -0.01038(19) O2 0.0465(8) 0.0217(6) 0.0201(6) 0.0026(5) -0.0037(5) 0.0007(5) C19 0.0206(7) 0.0149(7) 0.0186(7) -0.0015(6) 0.0029(6) -0.0002(6) C14 0.0246(8) 0.0170(7) 0.0207(8) -0.0025(6) -0.0035(6) -0.0010(6) C22 0.0212(8) 0.0369(10) 0.0231(8) 0.0103(7) 0.0001(6) 0.0020(7) C20 0.0165(7) 0.0226(8) 0.0168(7) -0.0017(6) 0.0014(5) -0.0028(6) C25 0.0191(7) 0.0230(8) 0.0166(7) 0.0004(6) 0.0012(6) -0.0033(6) C21 0.0149(7) 0.0249(8) 0.0263(8) 0.0030(6) 0.0045(6) -0.0010(6) C18 0.0229(8) 0.0241(8) 0.0201(7) 0.0015(6) -0.0019(6) -0.0003(6) C15 0.0354(9) 0.0200(8) 0.0185(8) 0.0002(6) 0.0028(6) -0.0002(7) C17 0.0206(8) 0.0301(9) 0.0285(9) 0.0045(7) 0.0007(6) -0.0005(7) C16 0.0270(9) 0.0252(8) 0.0273(8) 0.0045(7) 0.0073(7) 0.0004(7) C23 0.0235(8) 0.0413(10) 0.0168(7) 0.0018(7) -0.0025(6) -0.0040(7) C24 0.0291(9) 0.0268(8) 0.0154(7) -0.0022(6) 0.0018(6) -0.0035(7) C26 0.0309(9) 0.0242(9) 0.0427(11) 0.0047(8) 0.0074(8) 0.0042(7) S1 0.0588(3) 0.0186(2) 0.0162(2) 0.00273(15) 0.00797(18) 0.00911(19) Cl1 0.0682(3) 0.0281(2) 0.0187(2) -0.00016(16) 0.0107(2) 0.0149(2) C6 0.0214(8) 0.0196(8) 0.0187(7) 0.0038(6) 0.0031(6) -0.0001(6) C8 0.0229(8) 0.0288(8) 0.0192(8) 0.0053(6) -0.0034(6) -0.0023(6) C7 0.0270(8) 0.0182(7) 0.0142(7) 0.0026(6) 0.0033(6) 0.0025(6) C3 0.0261(8) 0.0210(8) 0.0221(8) 0.0057(6) -0.0043(6) -0.0030(6) C1 0.0223(8) 0.0206(8) 0.0187(7) -0.0008(6) 0.0031(6) 0.0018(6) C5 0.0251(8) 0.0226(8) 0.0169(7) 0.0008(6) 0.0040(6) 0.0006(6) C12 0.0213(8) 0.0130(7) 0.0301(8) 0.0061(6) 0.0028(6) 0.0020(6) C11 0.0272(8) 0.0198(8) 0.0272(9) 0.0012(6) -0.0108(6) -0.0017(6) O1 0.0320(7) 0.0599(9) 0.0292(7) 0.0096(6) -0.0137(6) -0.0136(6) C4 0.0264(8) 0.0202(8) 0.0240(8) -0.0006(6) -0.0003(6) 0.0005(6) C10 0.0355(9) 0.0301(9) 0.0158(7) -0.0013(7) -0.0026(7) 0.0094(7) C2 0.0215(8) 0.0274(8) 0.0157(7) 0.0033(6) -0.0004(6) -0.0033(6) C9 0.0197(8) 0.0468(11) 0.0195(8) 0.0062(7) 0.0022(6) 0.0012(7) C13 0.0256(9) 0.0266(9) 0.0616(13) 0.0095(9) 0.0107(9) -0.0019(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S2 C19 1.7690(16) . ? S2 C20 1.7795(16) . ? Cl2 C14 1.7434(16) . ? O2 C25 1.215(2) . ? C19 C18 1.394(2) . ? C19 C14 1.399(2) . ? C14 C15 1.381(2) . ? C22 C21 1.512(2) . ? C22 C23 1.513(3) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C20 C21 1.348(2) . ? C20 C25 1.489(2) . ? C25 C24 1.505(2) . ? C21 C26 1.497(2) . ? C18 C17 1.386(2) . ? C18 H18 0.95 . ? C15 C16 1.382(2) . ? C15 H15 0.95 . ? C17 C16 1.387(2) . ? C17 H17 0.95 . ? C16 H16 0.95 . ? C23 C24 1.516(2) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? S1 C6 1.7692(16) . ? S1 C7 1.7790(16) . ? Cl1 C1 1.7376(16) . ? C6 C5 1.394(2) . ? C6 C1 1.395(2) . ? C8 O1 1.212(2) . ? C8 C7 1.488(2) . ? C8 C9 1.509(2) . ? C7 C12 1.349(2) . ? C3 C2 1.384(2) . ? C3 C4 1.388(2) . ? C3 H3 0.95 . ? C1 C2 1.381(2) . ? C5 C4 1.390(2) . ? C5 H5 0.95 . ? C12 C13 1.496(2) . ? C12 C11 1.500(2) . ? C11 C10 1.509(2) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C4 H4 0.95 . ? C10 C9 1.513(3) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C2 H2 0.95 . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? 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 C19 S2 C20 102.73(7) . . ? C18 C19 C14 117.34(14) . . ? C18 C19 S2 123.74(12) . . ? C14 C19 S2 118.87(12) . . ? C15 C14 C19 122.10(15) . . ? C15 C14 Cl2 118.59(13) . . ? C19 C14 Cl2 119.31(12) . . ? C21 C22 C23 114.18(14) . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22A 108.7 . . ? C21 C22 H22B 108.7 . . ? C23 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C21 C20 C25 122.03(14) . . ? C21 C20 S2 122.17(13) . . ? C25 C20 S2 115.51(11) . . ? O2 C25 C20 120.98(14) . . ? O2 C25 C24 122.09(15) . . ? C20 C25 C24 116.92(14) . . ? C20 C21 C26 124.41(16) . . ? C20 C21 C22 120.98(15) . . ? C26 C21 C22 114.61(15) . . ? C17 C18 C19 120.76(15) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C14 C15 C16 119.65(15) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C18 C17 C16 120.73(16) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C15 C16 C17 119.41(15) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C22 C23 C24 110.39(14) . . ? C22 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? C22 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C25 C24 C23 112.68(14) . . ? C25 C24 H24A 109.1 . . ? C23 C24 H24A 109.1 . . ? C25 C24 H24B 109.1 . . ? C23 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C6 S1 C7 102.50(8) . . ? C5 C6 C1 117.61(14) . . ? C5 C6 S1 123.64(12) . . ? C1 C6 S1 118.75(12) . . ? O1 C8 C7 121.87(15) . . ? O1 C8 C9 121.98(16) . . ? C7 C8 C9 116.15(13) . . ? C12 C7 C8 121.79(14) . . ? C12 C7 S1 121.85(12) . . ? C8 C7 S1 116.32(12) . . ? C2 C3 C4 119.53(15) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C2 C1 C6 121.94(15) . . ? C2 C1 Cl1 118.59(12) . . ? C6 C1 Cl1 119.46(12) . . ? C4 C5 C6 120.80(15) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C12 C13 124.26(16) . . ? C7 C12 C11 121.20(15) . . ? C13 C12 C11 114.54(16) . . ? C12 C11 C10 113.54(13) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C3 C4 C5 120.37(15) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C11 C10 C9 109.75(14) . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C1 C2 C3 119.74(15) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C8 C9 C10 110.98(14) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _chemical_name_common 2-(2-chlorophenylthio)-3-methyl-2-cyclohexenone #===END # Attachment '- compound_3.cif' data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 679705' _audit_creation_date 2010-11-17T15:05:40-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-(2-bromophenylthio)-3-methyl-2-cyclohexenone ; _chemical_formula_moiety 'C13 H13 Br O S' _chemical_formula_sum 'C13 H13 Br O S' _chemical_formula_weight 297.20 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.730(5) _cell_length_b 15.142(5) _cell_length_c 20.590(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4904(3) _cell_formula_units_Z 16 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 7112 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 27.9 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.61 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2400 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.498 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS ver 2.03' _exptl_absorpt_correction_T_min 0.3351 _exptl_absorpt_correction_T_max 0.5413 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 103(2) _diffrn_radiation_probe X-ray _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_unetI/netI 0.0415 _diffrn_reflns_number 28443 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.9 _diffrn_reflns_theta_full 27.9 _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.971 _reflns_number_total 5696 _reflns_number_gt 4446 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0387P)^2^+2.8425P] 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_number_reflns 5696 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.754 _refine_diff_density_min -0.627 _refine_diff_density_rms 0.084 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.184659(18) 0.32073(2) 0.209111(12) 0.03087(9) Uani 1 1 d . . . Br2 Br 0.89007(2) 0.043172(18) 0.554879(12) 0.03595(10) Uani 1 1 d . . . S1 S 0.16057(4) 0.31618(4) 0.36308(3) 0.02151(14) Uani 1 1 d . . . S2 S 0.86853(5) 0.04137(4) 0.40099(3) 0.02914(17) Uani 1 1 d . . . C25 C 0.76761(16) 0.06280(16) 0.29192(12) 0.0217(5) Uani 1 1 d . . . C14 C 0.85847(15) 0.14652(16) 0.50854(11) 0.0174(5) Uani 1 1 d . . . C19 C 0.84967(16) 0.14285(16) 0.44154(11) 0.0181(5) Uani 1 1 d . . . C18 C 0.82650(15) 0.22052(16) 0.40983(12) 0.0204(5) Uani 1 1 d . . . H18 H 0.8198 0.2203 0.364 0.024 Uiso 1 1 calc R . . O1 O 0.14840(13) 0.49460(11) 0.41977(8) 0.0277(4) Uani 1 1 d . . . C22 C 0.91020(17) 0.11407(17) 0.20975(12) 0.0236(5) Uani 1 1 d . . . H22A H 0.928 0.0619 0.1841 0.028 Uiso 1 1 calc R . . H22B H 0.9479 0.1638 0.1977 0.028 Uiso 1 1 calc R . . O2 O 0.70591(12) 0.05167(14) 0.32663(9) 0.0355(5) Uani 1 1 d . . . C7 C 0.12715(15) 0.34348(16) 0.44320(11) 0.0174(5) Uani 1 1 d . . . C1 C 0.07788(15) 0.34626(15) 0.24839(11) 0.0185(5) Uani 1 1 d . . . C20 C 0.85533(16) 0.07032(15) 0.31797(11) 0.0185(5) Uani 1 1 d . . . C11 C 0.08375(18) 0.30583(18) 0.55571(12) 0.0261(6) Uani 1 1 d . . . H11A H 0.1338 0.2939 0.5835 0.031 Uiso 1 1 calc R . . H11B H 0.0368 0.2675 0.5709 0.031 Uiso 1 1 calc R . . C2 C 0.00964(17) 0.36530(16) 0.20827(12) 0.0229(5) Uani 1 1 d . . . H2 H 0.0165 0.365 0.1624 0.028 Uiso 1 1 calc R . . C13 C 0.09955(18) 0.18422(17) 0.47237(15) 0.0317(6) Uani 1 1 d . . . H13A H 0.0397 0.167 0.4687 0.048 Uiso 1 1 calc R . . H13B H 0.1263 0.1508 0.5076 0.048 Uiso 1 1 calc R . . H13C H 0.1289 0.1715 0.4314 0.048 Uiso 1 1 calc R . . C9 C 0.12124(17) 0.46174(16) 0.53109(12) 0.0223(5) Uani 1 1 d . . . H9A H 0.1011 0.5235 0.5344 0.027 Uiso 1 1 calc R . . H9B H 0.1766 0.4578 0.5538 0.027 Uiso 1 1 calc R . . C12 C 0.10533(15) 0.28120(16) 0.48674(12) 0.0209(5) Uani 1 1 d . . . C15 C 0.84632(16) 0.22359(17) 0.54308(11) 0.0207(5) Uani 1 1 d . . . H15 H 0.8535 0.224 0.5889 0.025 Uiso 1 1 calc R . . C6 C 0.07084(15) 0.34593(15) 0.31570(11) 0.0172(5) Uani 1 1 d . . . C21 C 0.92193(16) 0.09407(15) 0.28078(12) 0.0203(5) Uani 1 1 d . . . C16 C 0.82367(17) 0.30022(17) 0.51087(12) 0.0231(6) Uani 1 1 d . . . H16 H 0.8155 0.3536 0.5342 0.028 Uiso 1 1 calc R . . C10 C 0.05776(17) 0.40124(18) 0.56443(12) 0.0259(6) Uani 1 1 d . . . H10A H 0.0552 0.4155 0.6113 0.031 Uiso 1 1 calc R . . H10B H 0.0005 0.4106 0.5457 0.031 Uiso 1 1 calc R . . C17 C 0.81303(17) 0.29810(16) 0.44404(12) 0.0231(5) Uani 1 1 d . . . H17 H 0.7964 0.3501 0.4216 0.028 Uiso 1 1 calc R . . C23 C 0.82011(17) 0.13750(18) 0.19180(12) 0.0260(6) Uani 1 1 d . . . H23A H 0.8145 0.1398 0.1439 0.031 Uiso 1 1 calc R . . H23B H 0.8058 0.1965 0.2094 0.031 Uiso 1 1 calc R . . C5 C -0.00857(16) 0.36610(16) 0.34183(12) 0.0216(5) Uani 1 1 d . . . H5 H -0.0155 0.3665 0.3877 0.026 Uiso 1 1 calc R . . C26 C 1.01187(18) 0.10395(19) 0.30435(16) 0.0365(7) Uani 1 1 d . . . H26A H 1.0251 0.1668 0.3098 0.055 Uiso 1 1 calc R . . H26B H 1.0509 0.078 0.2725 0.055 Uiso 1 1 calc R . . H26C H 1.0183 0.0735 0.3461 0.055 Uiso 1 1 calc R . . C8 C 0.13348(16) 0.43844(16) 0.46046(11) 0.0185(5) Uani 1 1 d . . . C24 C 0.75915(17) 0.06924(19) 0.21904(11) 0.0267(6) Uani 1 1 d . . . H24A H 0.7001 0.0858 0.2077 0.032 Uiso 1 1 calc R . . H24B H 0.7713 0.011 0.1993 0.032 Uiso 1 1 calc R . . C3 C -0.06870(17) 0.38476(17) 0.23543(13) 0.0249(6) Uani 1 1 d . . . H3 H -0.116 0.3974 0.2083 0.03 Uiso 1 1 calc R . . C4 C -0.07775(16) 0.38564(17) 0.30244(13) 0.0244(6) Uani 1 1 d . . . H4 H -0.1312 0.3996 0.3214 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03075(15) 0.04175(17) 0.02011(13) -0.00256(11) 0.00614(11) 0.01156(12) Br2 0.0644(2) 0.02622(15) 0.01721(13) 0.00074(11) -0.00853(13) 0.01443(14) S1 0.0191(3) 0.0279(3) 0.0176(3) -0.0058(2) -0.0013(2) 0.0070(3) S2 0.0537(5) 0.0187(3) 0.0150(3) -0.0032(2) -0.0077(3) 0.0109(3) C25 0.0243(14) 0.0223(13) 0.0186(12) -0.0039(10) 0.0018(10) -0.0001(11) C14 0.0189(12) 0.0186(12) 0.0148(11) 0.0018(9) -0.0023(9) 0.0023(10) C19 0.0202(12) 0.0172(12) 0.0169(11) -0.0051(9) -0.0027(10) -0.0001(10) C18 0.0273(14) 0.0192(12) 0.0146(11) -0.0022(9) -0.0023(10) -0.0001(10) O1 0.0457(12) 0.0188(9) 0.0187(9) 0.0017(7) 0.0033(8) -0.0012(8) C22 0.0281(14) 0.0189(12) 0.0238(13) -0.0028(10) 0.0094(11) -0.0018(10) O2 0.0286(10) 0.0503(13) 0.0276(10) -0.0051(9) 0.0131(9) -0.0087(9) C7 0.0149(11) 0.0217(12) 0.0156(11) -0.0013(9) -0.0009(9) 0.0041(9) C1 0.0203(12) 0.0143(11) 0.0209(12) -0.0007(9) 0.0031(10) 0.0030(9) C20 0.0286(13) 0.0135(11) 0.0135(11) -0.0028(9) -0.0026(10) 0.0035(10) C11 0.0256(14) 0.0303(14) 0.0223(13) 0.0086(11) 0.0006(11) -0.0006(11) C2 0.0320(15) 0.0194(12) 0.0175(12) 0.0010(10) -0.0023(11) -0.0008(11) C13 0.0315(15) 0.0214(14) 0.0422(16) 0.0030(12) -0.0055(13) -0.0073(12) C9 0.0293(14) 0.0220(13) 0.0157(11) -0.0033(10) -0.0024(10) 0.0040(11) C12 0.0157(12) 0.0229(13) 0.0239(12) 0.0032(10) -0.0048(10) 0.0015(10) C15 0.0232(13) 0.0267(13) 0.0120(11) -0.0039(9) 0.0022(10) -0.0022(11) C6 0.0203(12) 0.0131(11) 0.0181(11) -0.0012(9) -0.0021(10) 0.0006(9) C21 0.0240(13) 0.0105(11) 0.0262(13) -0.0060(9) -0.0024(10) 0.0027(10) C16 0.0297(14) 0.0201(13) 0.0197(12) -0.0051(10) 0.0035(11) -0.0031(11) C10 0.0247(14) 0.0367(15) 0.0161(12) -0.0010(11) 0.0008(10) 0.0042(12) C17 0.0307(14) 0.0181(12) 0.0203(12) 0.0010(10) -0.0006(11) 0.0002(10) C23 0.0366(16) 0.0263(14) 0.0150(12) -0.0005(10) 0.0022(11) 0.0090(12) C5 0.0235(13) 0.0215(13) 0.0198(12) 0.0005(10) 0.0018(10) 0.0009(10) C26 0.0269(15) 0.0248(14) 0.058(2) -0.0077(14) -0.0104(14) -0.0008(12) C8 0.0209(12) 0.0193(12) 0.0153(11) -0.0010(9) -0.0020(10) 0.0033(10) C24 0.0206(13) 0.0423(16) 0.0172(12) -0.0049(11) -0.0030(10) 0.0007(12) C3 0.0261(14) 0.0253(13) 0.0234(12) 0.0062(11) -0.0071(11) -0.0007(11) C4 0.0189(13) 0.0271(13) 0.0273(13) 0.0039(11) 0.0005(11) 0.0017(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.904(2) . ? Br2 C14 1.899(2) . ? S1 C6 1.774(2) . ? S1 C7 1.780(2) . ? S2 C19 1.774(2) . ? S2 C20 1.777(2) . ? C25 O2 1.217(3) . ? C25 C20 1.485(4) . ? C25 C24 1.510(3) . ? C14 C15 1.380(3) . ? C14 C19 1.388(3) . ? C19 C18 1.393(3) . ? C18 C17 1.386(3) . ? C18 H18 0.95 . ? O1 C8 1.217(3) . ? C22 C21 1.505(3) . ? C22 C23 1.507(4) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C7 C12 1.346(3) . ? C7 C8 1.484(3) . ? C1 C2 1.385(3) . ? C1 C6 1.390(3) . ? C20 C21 1.346(4) . ? C11 C12 1.507(4) . ? C11 C10 1.512(4) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C2 C3 1.385(4) . ? C2 H2 0.95 . ? C13 C12 1.501(4) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C9 C8 1.509(3) . ? C9 C10 1.519(4) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C15 C16 1.383(4) . ? C15 H15 0.95 . ? C6 C5 1.394(3) . ? C21 C26 1.503(4) . ? C16 C17 1.387(3) . ? C16 H16 0.95 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C17 H17 0.95 . ? C23 C24 1.517(4) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C5 C4 1.389(3) . ? C5 H5 0.95 . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C3 C4 1.387(3) . ? C3 H3 0.95 . ? C4 H4 0.95 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 S1 C7 102.45(11) . . ? C19 S2 C20 102.68(11) . . ? O2 C25 C20 122.7(2) . . ? O2 C25 C24 121.5(2) . . ? C20 C25 C24 115.9(2) . . ? C15 C14 C19 122.2(2) . . ? C15 C14 Br2 118.31(17) . . ? C19 C14 Br2 119.52(18) . . ? C14 C19 C18 117.3(2) . . ? C14 C19 S2 119.07(18) . . ? C18 C19 S2 123.66(18) . . ? C17 C18 C19 121.1(2) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C21 C22 C23 113.6(2) . . ? C21 C22 H22A 108.8 . . ? C23 C22 H22A 108.8 . . ? C21 C22 H22B 108.8 . . ? C23 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C12 C7 C8 122.4(2) . . ? C12 C7 S1 122.01(19) . . ? C8 C7 S1 115.27(17) . . ? C2 C1 C6 122.2(2) . . ? C2 C1 Br1 118.21(18) . . ? C6 C1 Br1 119.54(18) . . ? C21 C20 C25 122.6(2) . . ? C21 C20 S2 121.5(2) . . ? C25 C20 S2 115.92(18) . . ? C12 C11 C10 114.2(2) . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C1 C2 C3 119.6(2) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C9 C10 112.2(2) . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C7 C12 C13 124.7(2) . . ? C7 C12 C11 120.8(2) . . ? C13 C12 C11 114.5(2) . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C1 C6 C5 117.1(2) . . ? C1 C6 S1 119.06(18) . . ? C5 C6 S1 123.81(19) . . ? C20 C21 C26 125.1(2) . . ? C20 C21 C22 120.7(2) . . ? C26 C21 C22 114.1(2) . . ? C15 C16 C17 119.2(2) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C11 C10 C9 110.2(2) . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C18 C17 C16 120.4(2) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C22 C23 C24 110.1(2) . . ? C22 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? C22 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.2 . . ? C4 C5 C6 121.6(2) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O1 C8 C7 121.7(2) . . ? O1 C8 C9 121.7(2) . . ? C7 C8 C9 116.7(2) . . ? C25 C24 C23 110.8(2) . . ? C25 C24 H24A 109.5 . . ? C23 C24 H24A 109.5 . . ? C25 C24 H24B 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? _chemical_name_common 2-(2-bromophenylthio)-3-methyl-2-cyclohexenone #===END # Attachment '- compound_1t.cif' data_compound_1t _database_code_depnum_ccdc_archive 'CCDC 679706' _audit_creation_date 2010-11-17T19:00:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; trans-6,9b-dimethyl-2,3,4a,9b-tetrahydro-1H-dibenzothiophene-4-one ; _chemical_formula_moiety 'C14 H16 O S' _chemical_formula_sum 'C14 H16 O S' _chemical_formula_weight 232.33 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.9911(2) _cell_length_b 17.8652(4) _cell_length_c 9.4401(2) _cell_angle_alpha 90 _cell_angle_beta 96.0200(10) _cell_angle_gamma 90 _cell_volume 1172.54(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9590 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 29.93 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_absorpt_correction_T_min 0.9399 _exptl_absorpt_correction_T_max 0.9876 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 153(2) _diffrn_radiation_probe X-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU RAXIS RAPID' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_unetI/netI 0.0411 _diffrn_reflns_number 13602 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 29.93 _diffrn_reflns_theta_full 29.93 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 3385 _reflns_number_gt 2475 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection RAPID-AUTO _computing_cell_refinement RAPID-AUTO _computing_data_reduction RAPID-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0597P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3385 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.038 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.491 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 0.54092(17) 0.01941(7) 0.75559(13) 0.0201(3) Uani 1 1 d . . . C2 C 0.58192(19) -0.04489(7) 0.83681(13) 0.0222(3) Uani 1 1 d . . . C3 C 0.4325(2) -0.09621(8) 0.84262(14) 0.0268(3) Uani 1 1 d . . . H3 H 0.4559 -0.141 0.8958 0.032 Uiso 1 1 calc R . . C4 C 0.2508(2) -0.08360(8) 0.77291(16) 0.0285(3) Uani 1 1 d . . . H4 H 0.1529 -0.1202 0.777 0.034 Uiso 1 1 calc R . . C5 C 0.21079(19) -0.01757(8) 0.69685(14) 0.0245(3) Uani 1 1 d . . . H5 H 0.0855 -0.0085 0.6508 0.029 Uiso 1 1 calc R . . C6 C 0.35560(18) 0.03459(7) 0.68912(13) 0.0196(2) Uani 1 1 d . . . C7 C 0.7774(2) -0.05766(8) 0.91493(15) 0.0286(3) Uani 1 1 d . . . H7A H 0.7862 -0.0318 1.007 0.043 Uiso 1 1 calc R . . H7B H 0.8759 -0.038 0.8583 0.043 Uiso 1 1 calc R . . H7C H 0.7978 -0.1114 0.9306 0.043 Uiso 1 1 calc R . . C8 C 0.33901(18) 0.11237(7) 0.62520(13) 0.0193(2) Uani 1 1 d . . . C9 C 0.1979(2) 0.12331(8) 0.49135(14) 0.0261(3) Uani 1 1 d . . . H9A H 0.2288 0.0876 0.4168 0.031 Uiso 1 1 calc R . . H9B H 0.0654 0.1128 0.514 0.031 Uiso 1 1 calc R . . C10 C 0.2092(2) 0.20333(9) 0.43546(16) 0.0320(3) Uani 1 1 d . . . H10A H 0.1489 0.2374 0.5005 0.038 Uiso 1 1 calc R . . H10B H 0.1335 0.2064 0.3409 0.038 Uiso 1 1 calc R . . C11 C 0.4154(2) 0.23083(9) 0.42134(15) 0.0300(3) Uani 1 1 d . . . H11A H 0.4527 0.2136 0.3284 0.036 Uiso 1 1 calc R . . H11B H 0.4142 0.2862 0.4197 0.036 Uiso 1 1 calc R . . C12 C 0.5684(2) 0.20558(8) 0.53673(14) 0.0250(3) Uani 1 1 d . . . C13 C 0.54338(18) 0.12581(7) 0.58193(13) 0.0195(2) Uani 1 1 d . . . H13 H 0.5574 0.0936 0.497 0.023 Uiso 1 1 calc R . . C14 C 0.2921(2) 0.16638(8) 0.74400(14) 0.0263(3) Uani 1 1 d . . . H14A H 0.2805 0.2174 0.7061 0.039 Uiso 1 1 calc R . . H14B H 0.3955 0.1645 0.8225 0.039 Uiso 1 1 calc R . . H14C H 0.1705 0.1515 0.7789 0.039 Uiso 1 1 calc R . . O1 O 0.70316(17) 0.24441(6) 0.58309(12) 0.0392(3) Uani 1 1 d . . . S1 S 0.71035(5) 0.09030(2) 0.72702(4) 0.02467(10) 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 0.0213(6) 0.0174(6) 0.0222(6) -0.0010(5) 0.0055(5) -0.0023(5) C2 0.0266(6) 0.0189(6) 0.0220(6) -0.0009(5) 0.0062(5) 0.0019(5) C3 0.0352(7) 0.0184(6) 0.0283(6) 0.0022(5) 0.0104(5) -0.0003(6) C4 0.0289(7) 0.0224(7) 0.0355(7) -0.0021(6) 0.0100(6) -0.0074(6) C5 0.0218(6) 0.0236(7) 0.0287(6) -0.0022(5) 0.0059(5) -0.0031(5) C6 0.0213(6) 0.0175(6) 0.0209(5) -0.0027(5) 0.0066(4) -0.0006(5) C7 0.0289(7) 0.0274(7) 0.0295(7) 0.0051(6) 0.0033(5) 0.0054(6) C8 0.0193(6) 0.0174(6) 0.0216(5) -0.0015(5) 0.0047(4) -0.0003(5) C9 0.0249(7) 0.0275(7) 0.0253(6) 0.0004(5) 0.0006(5) 0.0006(5) C10 0.0325(7) 0.0304(8) 0.0325(7) 0.0062(6) 0.0001(6) 0.0054(6) C11 0.0380(8) 0.0232(7) 0.0291(7) 0.0062(6) 0.0047(6) 0.0003(6) C12 0.0322(7) 0.0200(7) 0.0240(6) 0.0003(5) 0.0084(5) -0.0031(5) C13 0.0199(6) 0.0181(6) 0.0208(5) 0.0008(5) 0.0035(4) -0.0008(5) C14 0.0328(7) 0.0211(7) 0.0260(6) -0.0034(5) 0.0086(5) 0.0024(6) O1 0.0468(7) 0.0287(6) 0.0409(6) 0.0053(5) -0.0018(5) -0.0154(5) S1 0.02031(16) 0.02262(18) 0.03058(17) 0.00415(14) 0.00029(12) -0.00398(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.3942(18) . ? C1 C6 1.4055(17) . ? C1 S1 1.7738(13) . ? C2 C3 1.3955(19) . ? C2 C7 1.5007(19) . ? C3 C4 1.386(2) . ? C3 H3 0.95 . ? C4 C5 1.394(2) . ? C4 H4 0.95 . ? C5 C6 1.3836(18) . ? C5 H5 0.95 . ? C6 C8 1.5145(18) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 C9 1.5316(17) . ? C8 C14 1.5406(18) . ? C8 C13 1.5454(17) . ? C9 C10 1.529(2) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.542(2) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.5132(19) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 O1 1.2140(17) . ? C12 C13 1.5030(18) . ? C13 S1 1.8182(13) . ? C13 H13 1 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 122.09(12) . . ? C2 C1 S1 124.74(10) . . ? C6 C1 S1 113.16(9) . . ? C1 C2 C3 116.83(12) . . ? C1 C2 C7 121.30(12) . . ? C3 C2 C7 121.86(12) . . ? C4 C3 C2 121.81(13) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 120.41(13) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 119.27(13) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 119.46(12) . . ? C5 C6 C8 127.81(12) . . ? C1 C6 C8 112.55(11) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 C9 117.49(11) . . ? C6 C8 C14 107.33(10) . . ? C9 C8 C14 110.66(11) . . ? C6 C8 C13 102.33(10) . . ? C9 C8 C13 107.18(10) . . ? C14 C8 C13 111.61(11) . . ? C10 C9 C8 110.61(11) . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C9 C10 C11 114.23(12) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 116.06(11) . . ? C12 C11 H11A 108.3 . . ? C10 C11 H11A 108.3 . . ? C12 C11 H11B 108.3 . . ? C10 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? O1 C12 C13 123.27(13) . . ? O1 C12 C11 123.53(13) . . ? C13 C12 C11 113.11(11) . . ? C12 C13 C8 111.15(11) . . ? C12 C13 S1 117.39(9) . . ? C8 C13 S1 106.56(8) . . ? C12 C13 H13 107.1 . . ? C8 C13 H13 107.1 . . ? S1 C13 H13 107.1 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 S1 C13 88.71(6) . . ? _chemical_name_common ;trans-6,9b-dimethyl-2,3,4a,9b-tetrahydro-1H-dibenzothiophene- 4-one ; #=== END # Attachment '- compound_3c.cif' data_compound_3c _database_code_depnum_ccdc_archive 'CCDC 679707' _audit_creation_date 2010-11-17T19:25:02-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; cis-6-bromo-9b-methyl-2,3,4a,9b-tetrahydro-1H- dibenzothiophene-4-one ; _chemical_formula_moiety 'C13 H13 Br O S' _chemical_formula_sum 'C13 H13 Br O S' _chemical_formula_weight 297.2 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M ' P21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6070(19) _cell_length_b 7.5770(15) _cell_length_c 17.375(4) _cell_angle_alpha 90 _cell_angle_beta 103.40(3) _cell_angle_gamma 90 _cell_volume 1230.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 4831 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.87 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.486 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS ver 2.03' _exptl_absorpt_correction_T_min 0.3361 _exptl_absorpt_correction_T_max 0.7219 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 103(2) _diffrn_radiation_probe X-ray _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_unetI/netI 0.0381 _diffrn_reflns_number 10251 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.87 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.971 _reflns_number_total 2840 _reflns_number_gt 2553 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0425P)^2^+0.3879P] 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_number_reflns 2840 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.082 _refine_ls_wR_factor_gt 0.0793 _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 _refine_diff_density_max 0.923 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.087 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.5881(2) -0.0767(3) 0.27170(13) 0.0230(4) Uani 1 1 d . . . H1 H 0.5999 -0.1572 0.3146 0.028 Uiso 1 1 calc R . . C2 C 0.5501(2) 0.0982(3) 0.28148(11) 0.0183(4) Uani 1 1 d . . . C3 C 0.5341(2) 0.2150(2) 0.21752(12) 0.0188(4) Uani 1 1 d . . . C4 C 0.5543(2) 0.1568(3) 0.14544(12) 0.0203(4) Uani 1 1 d . . . C5 C 0.5909(2) -0.0178(3) 0.13512(13) 0.0236(4) Uani 1 1 d . . . H5 H 0.6037 -0.0577 0.0854 0.028 Uiso 1 1 calc R . . C6 C 0.6085(2) -0.1328(3) 0.19904(13) 0.0244(4) Uani 1 1 d . . . H6 H 0.635 -0.2519 0.1929 0.029 Uiso 1 1 calc R . . C7 C 0.5111(2) 0.1777(2) 0.35381(12) 0.0185(4) Uani 1 1 d . . . C8 C 0.5301(2) 0.3802(3) 0.34556(12) 0.0201(4) Uani 1 1 d . . . H8 H 0.633 0.41 0.3677 0.024 Uiso 1 1 calc R . . C9 C 0.4387(2) 0.4991(3) 0.38528(12) 0.0228(4) Uani 1 1 d . . . C10 C 0.2903(2) 0.4373(3) 0.38660(13) 0.0264(5) Uani 1 1 d . . . H10A H 0.2255 0.4601 0.3343 0.032 Uiso 1 1 calc R . . H10B H 0.2549 0.506 0.4266 0.032 Uiso 1 1 calc R . . C11 C 0.2864(2) 0.2406(3) 0.40590(13) 0.0248(4) Uani 1 1 d . . . H11A H 0.34 0.2196 0.4611 0.03 Uiso 1 1 calc R . . H11B H 0.1861 0.2031 0.4013 0.03 Uiso 1 1 calc R . . C12 C 0.3525(2) 0.1317(3) 0.34941(12) 0.0215(4) Uani 1 1 d . . . H12A H 0.2965 0.151 0.2946 0.026 Uiso 1 1 calc R . . H12B H 0.3455 0.0049 0.3619 0.026 Uiso 1 1 calc R . . C13 C 0.6084(2) 0.1135(3) 0.43152(12) 0.0251(4) Uani 1 1 d . . . H13A H 0.5787 0.1683 0.4762 0.038 Uiso 1 1 calc R . . H13B H 0.7077 0.1461 0.4329 0.038 Uiso 1 1 calc R . . H13C H 0.6011 -0.0151 0.4351 0.038 Uiso 1 1 calc R . . O1 O 0.48780(19) 0.6389(2) 0.41287(10) 0.0328(4) Uani 1 1 d . . . S1 S 0.48681(5) 0.43019(6) 0.23905(3) 0.02200(13) Uani 1 1 d . . . Br1 Br 0.52990(3) 0.31632(3) 0.059160(12) 0.03175(10) 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 0.0239(10) 0.0169(9) 0.0280(11) 0.0049(8) 0.0057(8) 0.0018(8) C2 0.0152(9) 0.0188(9) 0.0202(9) 0.0009(7) 0.0028(7) -0.0015(7) C3 0.0174(9) 0.0148(9) 0.0233(10) 0.0014(7) 0.0029(8) 0.0003(7) C4 0.0186(9) 0.0225(10) 0.0195(10) 0.0028(7) 0.0036(8) -0.0014(7) C5 0.0215(10) 0.0251(10) 0.0248(10) -0.0045(8) 0.0063(8) -0.0027(8) C6 0.0241(10) 0.0171(9) 0.0323(11) -0.0005(8) 0.0072(9) 0.0007(8) C7 0.0179(9) 0.0173(9) 0.0198(10) 0.0027(7) 0.0036(7) 0.0004(7) C8 0.0209(9) 0.0173(9) 0.0207(10) 0.0010(7) 0.0019(8) -0.0008(7) C9 0.0298(11) 0.0190(9) 0.0185(10) 0.0027(8) 0.0038(8) 0.0034(8) C10 0.0251(10) 0.0285(11) 0.0259(11) 0.0017(8) 0.0063(8) 0.0061(8) C11 0.0214(10) 0.0287(11) 0.0243(11) 0.0013(9) 0.0056(8) 0.0013(8) C12 0.0215(10) 0.0216(9) 0.0216(10) 0.0003(8) 0.0053(8) -0.0036(8) C13 0.0262(10) 0.0277(11) 0.0197(10) 0.0047(8) 0.0015(8) 0.0032(9) O1 0.0446(10) 0.0221(8) 0.0328(9) -0.0066(7) 0.0112(7) -0.0032(7) S1 0.0283(3) 0.0153(2) 0.0224(3) 0.00411(18) 0.0059(2) 0.00340(18) Br1 0.04413(17) 0.03058(15) 0.02040(14) 0.00615(8) 0.00723(10) 0.00105(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.389(3) . ? C1 C2 1.395(3) . ? C1 H1 0.95 . ? C2 C3 1.401(3) . ? C2 C7 1.517(3) . ? C3 C4 1.383(3) . ? C3 S1 1.756(2) . ? C4 C5 1.392(3) . ? C4 Br1 1.897(2) . ? C5 C6 1.391(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C13 1.533(3) . ? C7 C12 1.547(3) . ? C7 C8 1.556(3) . ? C8 C9 1.530(3) . ? C8 S1 1.840(2) . ? C8 H8 1 . ? C9 O1 1.212(3) . ? C9 C10 1.505(3) . ? C10 C11 1.531(3) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.529(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.85(18) . . ? C6 C1 H1 120.1 . . ? C2 C1 H1 120.1 . . ? C1 C2 C3 119.16(18) . . ? C1 C2 C7 126.87(17) . . ? C3 C2 C7 113.78(17) . . ? C4 C3 C2 120.26(18) . . ? C4 C3 S1 125.91(15) . . ? C2 C3 S1 113.83(15) . . ? C3 C4 C5 120.84(18) . . ? C3 C4 Br1 119.65(15) . . ? C5 C4 Br1 119.51(16) . . ? C6 C5 C4 118.70(19) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C1 C6 C5 121.18(19) . . ? C1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C2 C7 C13 112.74(16) . . ? C2 C7 C12 107.40(16) . . ? C13 C7 C12 111.38(17) . . ? C2 C7 C8 104.99(16) . . ? C13 C7 C8 109.48(16) . . ? C12 C7 C8 110.66(16) . . ? C9 C8 C7 116.55(17) . . ? C9 C8 S1 108.25(13) . . ? C7 C8 S1 106.96(13) . . ? C9 C8 H8 108.3 . . ? C7 C8 H8 108.3 . . ? S1 C8 H8 108.3 . . ? O1 C9 C10 123.3(2) . . ? O1 C9 C8 118.7(2) . . ? C10 C9 C8 117.95(18) . . ? C9 C10 C11 112.19(17) . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 110.49(17) . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C7 113.43(17) . . ? C11 C12 H12A 108.9 . . ? C7 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C7 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 S1 C8 90.80(9) . . ? #===END _chemical_name_common ;cis-6-bromo-9b-methyl-2,3,4a,9b-tetrahydro-1H- dibenzothiophene-4-one ; data_co_crystal_Cl_Br_1_1 _database_code_depnum_ccdc_archive 'CCDC 679709' _audit_creation_date 2010-11-17T17:10:32-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; mixed crystal ; _chemical_formula_moiety 'C26 H26 Br Cl O2 S2' _chemical_formula_sum 'C26 H26 Br Cl O2 S2' _chemical_formula_weight 549.96 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M Pbca 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 15.8902(4) _cell_length_b 15.2239(3) _cell_length_c 20.6540(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4996.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 41787 _cell_measurement_theta_min 1.47 _cell_measurement_theta_max 27.37 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.42 _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.941 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_absorpt_correction_T_min 0.3888 _exptl_absorpt_correction_T_max 0.4961 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 153(2) _diffrn_radiation_probe X-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU RAXIS RAPID' _diffrn_measurement_method \w _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_unetI/netI 0.0546 _diffrn_reflns_number 43366 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.37 _diffrn_reflns_theta_full 27.37 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 5653 _reflns_number_gt 2699 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection RAPID-AUTO _computing_cell_refinement RAPID-AUTO _computing_data_reduction RAPID-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0623P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5653 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 0.815 _refine_ls_restrained_S_all 0.815 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.36 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Cl Cl 0.1484 0.1585 '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' 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 0.17376(18) 1.29752(19) -0.00977(13) 0.0710(8) Uani 1 1 d . . . H1 H 0.1828 1.3503 -0.0333 0.085 Uiso 1 1 calc R . . C2 C 0.15086(17) 1.22239(19) -0.04082(12) 0.0660(7) Uani 1 1 d . A . H2 H 0.1434 1.2229 -0.0865 0.079 Uiso 1 1 calc R . . C3 C 0.13852(16) 1.14653(17) -0.00727(11) 0.0572(6) Uani 1 1 d . . . C4 C 0.14689(16) 1.14263(16) 0.05978(11) 0.0542(6) Uani 1 1 d . A . C5 C 0.16982(16) 1.21906(17) 0.09084(12) 0.0631(7) Uani 1 1 d . . . H5 H 0.1763 1.2191 0.1366 0.076 Uiso 1 1 calc R A . C6 C 0.18350(18) 1.29538(18) 0.05664(13) 0.0707(8) Uani 1 1 d . A . H6 H 0.1998 1.3472 0.079 0.085 Uiso 1 1 calc R . . C7 C 0.14350(17) 1.06883(16) 0.18225(11) 0.0552(6) Uani 1 1 d . A . C8 C 0.08080(17) 1.09368(15) 0.22137(13) 0.0599(7) Uani 1 1 d . . . C9 C 0.0957(2) 1.11146(19) 0.29125(13) 0.0774(9) Uani 1 1 d . . . H9A H 0.06 1.1614 0.3048 0.093 Uiso 1 1 calc R . . H9B H 0.0782 1.0594 0.3166 0.093 Uiso 1 1 calc R . . C10 C 0.1843(2) 1.1320(2) 0.30684(13) 0.0903(10) Uani 1 1 d . . . H10A H 0.1916 1.1341 0.3544 0.108 Uiso 1 1 calc R . . H10B H 0.1989 1.1905 0.2892 0.108 Uiso 1 1 calc R . . C11 C 0.24141(19) 1.0650(2) 0.27915(12) 0.0868(10) Uani 1 1 d . . . H11A H 0.23 1.0074 0.2997 0.104 Uiso 1 1 calc R . . H11B H 0.3005 1.0812 0.2886 0.104 Uiso 1 1 calc R . . C12 C 0.22972(18) 1.0574(2) 0.20731(12) 0.0731(8) Uani 1 1 d . . . C13 C -0.0090(2) 1.1047(2) 0.19970(18) 0.1081(12) Uani 1 1 d . . . H13A H -0.0225 1.1674 0.1969 0.162 Uiso 1 1 calc R . . H13B H -0.0466 1.0765 0.231 0.162 Uiso 1 1 calc R . . H13C H -0.0164 1.0774 0.1571 0.162 Uiso 1 1 calc R . . C14 C 0.11971(19) 0.95640(19) 0.53095(12) 0.0738(8) Uani 1 1 d . . . H14A H 0.1745 0.9539 0.5537 0.089 Uiso 1 1 calc R . . H14B H 0.0979 1.0171 0.5348 0.089 Uiso 1 1 calc R . . C15 C 0.13287(17) 0.93526(18) 0.46097(11) 0.0578(7) Uani 1 1 d . . . C16 C 0.12757(15) 0.84191(17) 0.44195(11) 0.0518(6) Uani 1 1 d . B . C17 C 0.10621(15) 0.77874(18) 0.48389(13) 0.0641(7) Uani 1 1 d . . . C18 C 0.08503(19) 0.8015(2) 0.55298(13) 0.0826(9) Uani 1 1 d . . . H18A H 0.0381 0.7636 0.5676 0.099 Uiso 1 1 calc R . . H18B H 0.1344 0.7884 0.5806 0.099 Uiso 1 1 calc R . . C19 C 0.0606(2) 0.8957(2) 0.56271(13) 0.0919(10) Uani 1 1 d . . . H19A H 0.0034 0.9052 0.545 0.11 Uiso 1 1 calc R . . H19B H 0.0589 0.9086 0.6097 0.11 Uiso 1 1 calc R . . C20 C 0.07367(16) 0.84513(15) 0.31418(11) 0.0523(6) Uani 1 1 d . B . C21 C 0.08176(17) 0.84275(15) 0.24699(12) 0.0583(7) Uani 1 1 d . . . C22 C 0.0146(2) 0.86066(18) 0.20691(12) 0.0738(8) Uani 1 1 d . B . H22 H 0.0216 0.858 0.1613 0.089 Uiso 1 1 calc R . . C23 C -0.0614(2) 0.8820(2) 0.23235(14) 0.0804(9) Uani 1 1 d . . . H23 H -0.1076 0.8946 0.2047 0.097 Uiso 1 1 calc R B . C24 C -0.07110(19) 0.8852(2) 0.29866(14) 0.0774(8) Uani 1 1 d . B . H24 H -0.1242 0.9 0.3168 0.093 Uiso 1 1 calc R . . C25 C -0.00421(16) 0.86699(16) 0.33854(12) 0.0610(7) Uani 1 1 d . . . H25 H -0.0119 0.8695 0.3841 0.073 Uiso 1 1 calc R B . C26 C 0.1027(2) 0.6831(2) 0.46709(19) 0.1055(12) Uani 1 1 d . . . H26A H 0.1303 0.6734 0.4253 0.158 Uiso 1 1 calc R . . H26B H 0.0438 0.6643 0.4644 0.158 Uiso 1 1 calc R . . H26C H 0.1316 0.649 0.5006 0.158 Uiso 1 1 calc R . . O1 O 0.28840(14) 1.04266(19) 0.17153(10) 0.1267(10) Uani 1 1 d . . . O2 O 0.14755(15) 0.99196(14) 0.42218(9) 0.0920(6) Uani 1 1 d . . . S1 S 0.12727(6) 1.04248(5) 0.09977(3) 0.0881(3) Uani 1 1 d . . . S2 S 0.16158(4) 0.81760(5) 0.36198(3) 0.0731(3) Uani 1 1 d . . . Cl1 Cl 0.1139(5) 1.0501(4) -0.0492(3) 0.193(3) Uani 0.5 1 d P A 1 Cl2 Cl 0.1769(4) 0.8068(5) 0.2152(3) 0.233(4) Uani 0.5 1 d P B 1 Br1 Br 0.10742(13) 1.04789(9) -0.05210(6) 0.0940(5) Uani 0.5 1 d P A 2 Br2 Br 0.18285(8) 0.81784(9) 0.20928(6) 0.0819(3) Uani 0.5 1 d P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.088(2) 0.0607(18) 0.0646(17) 0.0192(15) 0.0114(15) 0.0079(15) C2 0.0740(19) 0.079(2) 0.0447(13) 0.0141(14) 0.0025(13) 0.0066(16) C3 0.0630(16) 0.0613(16) 0.0473(13) 0.0018(13) -0.0059(12) -0.0011(14) C4 0.0554(15) 0.0571(16) 0.0500(13) 0.0060(12) -0.0097(12) -0.0013(13) C5 0.0795(19) 0.0615(17) 0.0484(13) 0.0081(13) -0.0060(13) -0.0012(14) C6 0.090(2) 0.0537(17) 0.0685(17) 0.0055(15) 0.0021(16) -0.0017(15) C7 0.0668(17) 0.0525(14) 0.0463(12) 0.0091(11) -0.0046(13) -0.0044(13) C8 0.0629(18) 0.0436(14) 0.0733(17) 0.0168(13) 0.0015(14) 0.0001(13) C9 0.095(2) 0.0647(18) 0.0721(19) 0.0057(15) 0.0316(17) 0.0033(17) C10 0.117(3) 0.104(3) 0.0501(15) -0.0026(17) 0.0107(17) -0.034(2) C11 0.0649(19) 0.139(3) 0.0568(15) 0.0205(19) -0.0095(15) -0.008(2) C12 0.067(2) 0.096(2) 0.0561(15) 0.0175(16) 0.0135(14) 0.0114(17) C13 0.068(2) 0.094(2) 0.162(3) 0.032(2) -0.014(2) 0.0091(18) C14 0.094(2) 0.0787(19) 0.0490(14) -0.0067(14) -0.0040(14) 0.0128(17) C15 0.0642(17) 0.0642(17) 0.0451(13) 0.0002(13) -0.0017(12) 0.0083(14) C16 0.0454(14) 0.0616(16) 0.0483(13) -0.0039(12) -0.0047(11) 0.0069(12) C17 0.0513(16) 0.0670(17) 0.0741(18) 0.0100(15) -0.0131(13) -0.0014(13) C18 0.076(2) 0.107(3) 0.0645(17) 0.0339(18) 0.0011(15) -0.0068(18) C19 0.096(2) 0.125(3) 0.0545(16) -0.0011(19) 0.0090(17) 0.009(2) C20 0.0623(17) 0.0470(14) 0.0478(12) -0.0057(11) -0.0013(12) 0.0037(13) C21 0.0740(19) 0.0467(14) 0.0542(14) -0.0057(12) 0.0046(14) 0.0066(13) C22 0.100(3) 0.0703(19) 0.0507(14) -0.0004(14) -0.0109(16) 0.0043(17) C23 0.082(2) 0.089(2) 0.0708(19) 0.0132(17) -0.0216(17) 0.0037(19) C24 0.0629(19) 0.091(2) 0.078(2) 0.0087(17) -0.0054(16) 0.0051(16) C25 0.0554(17) 0.0734(18) 0.0542(13) 0.0003(14) -0.0023(13) 0.0064(14) C26 0.108(3) 0.068(2) 0.141(3) 0.013(2) -0.028(2) -0.0186(19) O1 0.0942(16) 0.200(3) 0.0854(15) 0.0308(17) 0.0362(13) 0.0526(18) O2 0.1444(18) 0.0669(13) 0.0649(12) 0.0108(11) 0.0093(13) -0.0049(13) S1 0.1561(8) 0.0594(5) 0.0488(4) 0.0086(3) -0.0202(4) -0.0242(5) S2 0.0645(5) 0.1009(6) 0.0538(4) -0.0181(4) -0.0038(3) 0.0262(4) Cl1 0.268(9) 0.202(6) 0.110(4) -0.019(4) -0.003(4) -0.040(5) Cl2 0.242(6) 0.330(8) 0.125(4) 0.010(4) 0.033(3) 0.123(5) Br1 0.1650(14) 0.0724(7) 0.0447(5) -0.0002(6) -0.0264(7) -0.0377(8) Br2 0.0826(6) 0.1111(7) 0.0521(4) -0.0126(5) 0.0159(4) 0.0273(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.361(4) . ? C1 C6 1.381(3) . ? C1 H1 0.95 . ? C2 C3 1.361(3) . ? C2 H2 0.95 . ? C3 C4 1.392(3) . ? C3 Cl1 1.748(7) . ? C3 Br1 1.832(3) . ? C4 C5 1.378(3) . ? C4 S1 1.762(2) . ? C5 C6 1.377(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.337(3) . ? C7 C12 1.475(4) . ? C7 S1 1.769(2) . ? C8 C9 1.488(4) . ? C8 C13 1.505(4) . ? C9 C10 1.477(4) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.481(4) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.500(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 O1 1.211(3) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 C19 1.472(4) . ? C14 C15 1.496(3) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 O2 1.200(3) . ? C15 C16 1.477(3) . ? C16 C17 1.338(3) . ? C16 S2 1.777(2) . ? C17 C26 1.498(4) . ? C17 C18 1.507(4) . ? C18 C19 1.498(4) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 C25 1.377(3) . ? C20 C21 1.394(3) . ? C20 S2 1.761(2) . ? C21 C22 1.378(4) . ? C21 Cl2 1.737(7) . ? C21 Br2 1.825(3) . ? C22 C23 1.357(4) . ? C22 H22 0.95 . ? C23 C24 1.379(4) . ? C23 H23 0.95 . ? C24 C25 1.373(3) . ? C24 H24 0.95 . ? C25 H25 0.95 . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.6(3) . . ? C2 C1 H1 120.7 . . ? C6 C1 H1 120.7 . . ? C1 C2 C3 120.8(2) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C2 C3 C4 121.9(2) . . ? C2 C3 Cl1 119.5(3) . . ? C4 C3 Cl1 118.6(3) . . ? C2 C3 Br1 118.49(19) . . ? C4 C3 Br1 119.6(2) . . ? Cl1 C3 Br1 2.9(3) . . ? C5 C4 C3 116.9(2) . . ? C5 C4 S1 124.01(18) . . ? C3 C4 S1 119.1(2) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.8(3) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C12 120.9(2) . . ? C8 C7 S1 122.5(2) . . ? C12 C7 S1 116.53(19) . . ? C7 C8 C9 121.3(2) . . ? C7 C8 C13 123.9(3) . . ? C9 C8 C13 114.8(3) . . ? C10 C9 C8 113.7(2) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C11 110.7(3) . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C10 C11 C12 111.0(2) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108 . . ? O1 C12 C7 121.5(2) . . ? O1 C12 C11 121.5(3) . . ? C7 C12 C11 117.0(2) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 112.6(2) . . ? C19 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C19 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? O2 C15 C16 121.7(2) . . ? O2 C15 C14 121.2(3) . . ? C16 C15 C14 117.1(2) . . ? C17 C16 C15 122.3(2) . . ? C17 C16 S2 122.0(2) . . ? C15 C16 S2 115.49(19) . . ? C16 C17 C26 123.9(3) . . ? C16 C17 C18 120.3(2) . . ? C26 C17 C18 115.8(3) . . ? C19 C18 C17 113.9(2) . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18B 108.8 . . ? C17 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C14 C19 C18 112.1(3) . . ? C14 C19 H19A 109.2 . . ? C18 C19 H19A 109.2 . . ? C14 C19 H19B 109.2 . . ? C18 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C25 C20 C21 116.9(2) . . ? C25 C20 S2 124.45(18) . . ? C21 C20 S2 118.6(2) . . ? C22 C21 C20 121.4(3) . . ? C22 C21 Cl2 120.6(3) . . ? C20 C21 Cl2 117.7(3) . . ? C22 C21 Br2 117.8(2) . . ? C20 C21 Br2 120.8(2) . . ? Cl2 C21 Br2 6.8(3) . . ? C23 C22 C21 120.3(3) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 119.5(3) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C25 C24 C23 120.1(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C20 121.7(2) . . ? C24 C25 H25 119.2 . . ? C20 C25 H25 119.2 . . ? C17 C26 H26A 109.5 . . ? C17 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C17 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C4 S1 C7 103.26(11) . . ? C20 S2 C16 103.31(11) . . ? _chemical_name_common 'mixed crystal' #=== END # Attachment '- co_crystal_Me_Br_1_1.cif' data_co_crystal_Me_Br_1_1 _database_code_depnum_ccdc_archive 'CCDC 679710' _audit_creation_date 2010-11-17T17:34:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13.51 H14.53 Br0.49 O S, C13.67 H15.02 Br0.33 O S' _chemical_formula_sum 'C27.18 H29.54 Br0.82 O2 S2' _chemical_formula_weight 517.80 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.591(3) _cell_length_b 15.064(3) _cell_length_c 20.669(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4854.4(17) _cell_formula_units_Z 8 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6521 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 27.91 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2155.7 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.590 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS ver 2.03' _exptl_absorpt_correction_T_min 0.7039 _exptl_absorpt_correction_T_max 0.9115 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 103(2) _diffrn_radiation_probe X-ray _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_unetI/netI 0.0322 _diffrn_reflns_number 40034 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.91 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _reflns_number_total 5714 _reflns_number_gt 4730 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. DFIX and EADP restraints were applied to C1-C27 and C14-C28. Thus, the reliability of the site occupancy factors for C27/Br1 pair and for C28/Br2 is not high. o-Me:o-Br ratio in X3(1:3=1:1) was determined by 1H NMR spectrometry. ; _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^)+(0.0318P)^2^+6.5110P] 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_number_reflns 5714 _refine_ls_number_parameters 301 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.52 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C26 C 0.01540(19) 0.4017(2) 0.80772(18) 0.0476(8) Uani 1 1 d . . . H26A H 0.02 0.4333 0.849 0.071 Uiso 1 1 calc R . . H26B H 0.0554 0.4276 0.7764 0.071 Uiso 1 1 calc R . . H26C H 0.0294 0.3389 0.8142 0.071 Uiso 1 1 calc R . . O2 O -0.29339(13) 0.44946(16) 0.82441(10) 0.0484(6) Uani 1 1 d . . . C1 C 0.08059(16) 0.34261(17) 0.24767(12) 0.0283(5) Uani 1 1 d D . . C2 C 0.01032(18) 0.36041(17) 0.20861(12) 0.0312(6) Uani 1 1 d . B . H2 H 0.0165 0.3591 0.1629 0.037 Uiso 1 1 calc R . . C3 C -0.06834(18) 0.38000(18) 0.23541(13) 0.0343(6) Uani 1 1 d . . . H3 H -0.1163 0.3916 0.2084 0.041 Uiso 1 1 calc R B . C4 C -0.07695(18) 0.38266(19) 0.30233(13) 0.0348(6) Uani 1 1 d . B . H4 H -0.1308 0.3973 0.321 0.042 Uiso 1 1 calc R . . C5 C -0.00748(16) 0.36405(17) 0.34193(12) 0.0290(5) Uani 1 1 d . . . H5 H -0.0143 0.3652 0.3876 0.035 Uiso 1 1 calc R B . C6 C 0.07206(15) 0.34370(15) 0.31540(11) 0.0238(5) Uani 1 1 d . B . C7 C 0.13006(15) 0.34363(16) 0.44296(11) 0.0234(5) Uani 1 1 d . B . C8 C 0.13797(16) 0.43916(16) 0.45992(11) 0.0249(5) Uani 1 1 d . . . C9 C 0.12441(17) 0.46329(17) 0.53013(11) 0.0277(5) Uani 1 1 d . . . H9A H 0.1048 0.5257 0.5328 0.033 Uiso 1 1 calc R . . H9B H 0.1798 0.4589 0.5533 0.033 Uiso 1 1 calc R . . C10 C 0.05936(17) 0.40420(19) 0.56345(12) 0.0321(6) Uani 1 1 d . . . H10A H 0.0566 0.4192 0.61 0.039 Uiso 1 1 calc R . . H10B H 0.0019 0.4141 0.5445 0.039 Uiso 1 1 calc R . . C11 C 0.08472(17) 0.30792(18) 0.55534(12) 0.0320(6) Uani 1 1 d . . . H11A H 0.1351 0.2957 0.5831 0.038 Uiso 1 1 calc R . . H11B H 0.037 0.27 0.5707 0.038 Uiso 1 1 calc R . . C12 C 0.10630(15) 0.28243(16) 0.48675(12) 0.0273(5) Uani 1 1 d . . . C13 C 0.0991(2) 0.18504(18) 0.47288(16) 0.0411(7) Uani 1 1 d . . . H13A H 0.0387 0.1692 0.4671 0.062 Uiso 1 1 calc R . . H13B H 0.1231 0.1513 0.5092 0.062 Uiso 1 1 calc R . . H13C H 0.131 0.171 0.4333 0.062 Uiso 1 1 calc R . . C14 C -0.14043(16) 0.36209(18) 1.01053(12) 0.0291(5) Uani 1 1 d D . . C15 C -0.15138(16) 0.28372(18) 1.04415(12) 0.0295(5) Uani 1 1 d . A . H15 H -0.1439 0.2834 1.0898 0.035 Uiso 1 1 calc R . . C16 C -0.17305(17) 0.20558(18) 1.01294(12) 0.0316(6) Uani 1 1 d . . . H16 H -0.1808 0.1523 1.0368 0.038 Uiso 1 1 calc R A . C17 C -0.18329(18) 0.20648(17) 0.94612(13) 0.0319(6) Uani 1 1 d . A . H17 H -0.1988 0.1534 0.9242 0.038 Uiso 1 1 calc R . . C18 C -0.17110(17) 0.28407(17) 0.91126(12) 0.0293(5) Uani 1 1 d . . . H18 H -0.1775 0.2838 0.8656 0.035 Uiso 1 1 calc R A . C19 C -0.14951(16) 0.36212(16) 0.94296(11) 0.0258(5) Uani 1 1 d . A . C20 C -0.14253(16) 0.43366(16) 0.81858(11) 0.0254(5) Uani 1 1 d . A . C21 C -0.07433(16) 0.40960(16) 0.78248(13) 0.0283(5) Uani 1 1 d . . . C22 C -0.08409(18) 0.38802(17) 0.71174(13) 0.0328(6) Uani 1 1 d . . . H22A H -0.067 0.4405 0.686 0.039 Uiso 1 1 calc R . . H22B H -0.0445 0.339 0.7006 0.039 Uiso 1 1 calc R . . C23 C -0.17346(19) 0.36168(19) 0.69315(12) 0.0360(6) Uani 1 1 d . . . H23A H -0.1868 0.3025 0.7114 0.043 Uiso 1 1 calc R . . H23B H -0.1779 0.3578 0.6455 0.043 Uiso 1 1 calc R . . C24 C -0.23706(17) 0.4289(2) 0.71816(12) 0.0349(6) Uani 1 1 d . . . H24A H -0.2959 0.4098 0.7067 0.042 Uiso 1 1 calc R . . H24B H -0.2262 0.487 0.6974 0.042 Uiso 1 1 calc R . . C25 C -0.23015(17) 0.43862(17) 0.79075(12) 0.0295(5) Uani 1 1 d . . . O1 O 0.15604(14) 0.49439(12) 0.41949(9) 0.0375(5) Uani 1 1 d . . . S1 S 0.16266(4) 0.31503(4) 0.36297(3) 0.02893(16) Uani 1 1 d . . . S2 S -0.13223(5) 0.46372(4) 0.90154(3) 0.03756(19) Uani 1 1 d . . . Br2 Br -0.10739(12) 0.45595(12) 1.05489(8) 0.0391(4) Uani 0.3281(17) 1 d P A 1 C28 C -0.1229(6) 0.4516(6) 1.0472(4) 0.0291(5) Uani 0.6719(17) 1 d PD A 2 H28A H -0.1688 0.494 1.0375 0.044 Uiso 0.6719(17) 1 calc PR A 2 H28B H -0.0678 0.4762 1.0331 0.044 Uiso 0.6719(17) 1 calc PR A 2 H28C H -0.1212 0.4405 1.0939 0.044 Uiso 0.6719(17) 1 calc PR A 2 Br1 Br 0.18559(5) 0.31991(7) 0.20939(4) 0.0331(2) Uani 0.4913(18) 1 d P B 3 C27 C 0.1662(6) 0.3102(7) 0.2149(5) 0.0283(5) Uani 0.5087(18) 1 d PD B 4 H27A H 0.1689 0.2453 0.2164 0.042 Uiso 0.5087(18) 1 calc PR B 4 H27B H 0.2153 0.3352 0.2382 0.042 Uiso 0.5087(18) 1 calc PR B 4 H27C H 0.1675 0.3301 0.1698 0.042 Uiso 0.5087(18) 1 calc PR B 4 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 C26 0.0332(15) 0.0335(15) 0.076(2) 0.0117(15) -0.0087(15) 0.0014(12) O2 0.0380(11) 0.0719(16) 0.0354(11) 0.0054(10) 0.0116(9) 0.0132(11) C1 0.0306(13) 0.0293(12) 0.0249(11) -0.0017(10) 0.0003(10) -0.0013(10) C2 0.0420(15) 0.0281(13) 0.0235(12) 0.0016(10) -0.0040(11) -0.0012(11) C3 0.0344(14) 0.0365(15) 0.0319(14) 0.0069(11) -0.0087(11) 0.0013(11) C4 0.0292(13) 0.0404(15) 0.0346(14) 0.0054(12) 0.0003(11) 0.0034(11) C5 0.0308(13) 0.0324(14) 0.0238(12) 0.0006(10) 0.0000(10) 0.0027(11) C6 0.0252(11) 0.0213(11) 0.0248(11) -0.0015(9) -0.0034(9) 0.0005(9) C7 0.0232(11) 0.0271(12) 0.0200(11) -0.0037(9) -0.0017(9) 0.0032(9) C8 0.0275(12) 0.0253(12) 0.0219(11) 0.0003(9) -0.0009(9) 0.0032(9) C9 0.0368(14) 0.0269(12) 0.0193(11) -0.0019(9) -0.0023(10) 0.0034(10) C10 0.0310(13) 0.0440(15) 0.0213(12) 0.0003(11) 0.0028(10) 0.0053(12) C11 0.0322(13) 0.0370(14) 0.0269(13) 0.0075(11) 0.0015(11) -0.0036(11) C12 0.0231(12) 0.0278(12) 0.0311(13) -0.0002(10) -0.0063(10) 0.0005(10) C13 0.0444(16) 0.0277(14) 0.0512(17) 0.0011(13) -0.0074(14) -0.0060(12) C14 0.0267(12) 0.0378(13) 0.0229(11) 0.0028(10) -0.0021(9) -0.0025(10) C15 0.0260(12) 0.0422(15) 0.0202(11) 0.0057(10) 0.0012(10) 0.0060(11) C16 0.0365(14) 0.0300(13) 0.0282(13) 0.0087(11) 0.0055(11) 0.0089(11) C17 0.0430(15) 0.0246(12) 0.0281(13) 0.0030(10) 0.0017(11) 0.0025(11) C18 0.0372(14) 0.0286(13) 0.0220(11) 0.0035(10) -0.0014(10) 0.0030(11) C19 0.0262(12) 0.0269(12) 0.0242(11) 0.0065(10) -0.0044(10) 0.0001(10) C20 0.0340(13) 0.0251(12) 0.0170(10) 0.0042(9) -0.0016(9) -0.0021(10) C21 0.0304(13) 0.0189(11) 0.0357(13) 0.0086(10) -0.0001(11) -0.0022(10) C22 0.0394(15) 0.0266(13) 0.0325(13) 0.0034(11) 0.0140(11) 0.0039(11) C23 0.0507(17) 0.0370(15) 0.0204(12) 0.0008(11) 0.0056(11) -0.0067(13) C24 0.0304(14) 0.0501(17) 0.0242(12) 0.0044(12) -0.0033(10) -0.0010(12) C25 0.0319(13) 0.0322(13) 0.0243(12) 0.0058(10) 0.0051(10) 0.0042(11) O1 0.0610(13) 0.0276(9) 0.0239(9) 0.0031(7) 0.0044(9) -0.0011(9) S1 0.0263(3) 0.0369(4) 0.0235(3) -0.0080(3) -0.0023(2) 0.0080(3) S2 0.0640(5) 0.0272(3) 0.0215(3) 0.0034(2) -0.0080(3) -0.0104(3) Br2 0.0654(11) 0.0286(5) 0.0234(6) 0.0003(4) -0.0109(5) -0.0172(6) C28 0.0267(12) 0.0378(13) 0.0229(11) 0.0028(10) -0.0021(9) -0.0025(10) Br1 0.0311(4) 0.0446(5) 0.0236(3) -0.0021(3) 0.0059(3) 0.0092(3) C27 0.0306(13) 0.0293(12) 0.0249(11) -0.0017(10) 0.0003(10) -0.0013(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C26 C21 1.498(4) . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? O2 C25 1.218(3) . ? C1 C2 1.387(4) . ? C1 C6 1.406(3) . ? C1 C27 1.574(9) . ? C1 Br1 1.850(3) . ? C2 C3 1.378(4) . ? C2 H2 0.95 . ? C3 C4 1.390(4) . ? C3 H3 0.95 . ? C4 C5 1.386(4) . ? C4 H4 0.95 . ? C5 C6 1.390(3) . ? C5 H5 0.95 . ? C6 S1 1.775(2) . ? C7 C12 1.344(3) . ? C7 C8 1.486(3) . ? C7 S1 1.783(2) . ? C8 O1 1.212(3) . ? C8 C9 1.511(3) . ? C9 C10 1.515(4) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.513(4) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.507(4) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 C13 1.499(4) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 C15 1.381(4) . ? C14 C19 1.404(3) . ? C14 C28 1.571(9) . ? C14 Br2 1.762(3) . ? C15 C16 1.384(4) . ? C15 H15 0.95 . ? C16 C17 1.390(4) . ? C16 H16 0.95 . ? C17 C18 1.386(3) . ? C17 H17 0.95 . ? C18 C19 1.387(4) . ? C18 H18 0.95 . ? C19 S2 1.774(2) . ? C20 C21 1.349(4) . ? C20 C25 1.484(4) . ? C20 S2 1.781(2) . ? C21 C22 1.505(4) . ? C22 C23 1.499(4) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C23 C24 1.508(4) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 C25 1.511(3) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? 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 C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C2 C1 C6 120.2(2) . . ? C2 C1 C27 118.6(5) . . ? C6 C1 C27 120.8(5) . . ? C2 C1 Br1 119.1(2) . . ? C6 C1 Br1 120.77(19) . . ? C27 C1 Br1 7.5(4) . . ? C3 C2 C1 120.7(2) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.5(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 118.7(2) . . ? C5 C6 S1 123.04(19) . . ? C1 C6 S1 118.26(19) . . ? C12 C7 C8 121.9(2) . . ? C12 C7 S1 122.50(19) . . ? C8 C7 S1 115.41(17) . . ? O1 C8 C7 121.4(2) . . ? O1 C8 C9 122.0(2) . . ? C7 C8 C9 116.6(2) . . ? C8 C9 C10 112.9(2) . . ? C8 C9 H9A 109 . . ? C10 C9 H9A 109 . . ? C8 C9 H9B 109 . . ? C10 C9 H9B 109 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 109.7(2) . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 114.0(2) . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C7 C12 C13 124.3(2) . . ? C7 C12 C11 121.3(2) . . ? C13 C12 C11 114.4(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 119.2(2) . . ? C15 C14 C28 120.8(4) . . ? C19 C14 C28 119.8(4) . . ? C15 C14 Br2 117.4(2) . . ? C19 C14 Br2 123.2(2) . . ? C28 C14 Br2 7.8(4) . . ? C14 C15 C16 121.5(2) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C15 C16 C17 118.9(2) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C18 C17 C16 120.6(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.1(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 119.6(2) . . ? C18 C19 S2 122.68(19) . . ? C14 C19 S2 117.7(2) . . ? C21 C20 C25 121.7(2) . . ? C21 C20 S2 122.0(2) . . ? C25 C20 S2 116.32(18) . . ? C20 C21 C26 124.4(3) . . ? C20 C21 C22 121.0(2) . . ? C26 C21 C22 114.5(2) . . ? C23 C22 C21 113.6(2) . . ? C23 C22 H22A 108.8 . . ? C21 C22 H22A 108.8 . . ? C23 C22 H22B 108.8 . . ? C21 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C22 C23 C24 110.2(2) . . ? C22 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? C22 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C23 C24 C25 111.0(2) . . ? C23 C24 H24A 109.4 . . ? C25 C24 H24A 109.4 . . ? C23 C24 H24B 109.4 . . ? C25 C24 H24B 109.4 . . ? H24A C24 H24B 108 . . ? O2 C25 C20 122.1(2) . . ? O2 C25 C24 121.5(2) . . ? C20 C25 C24 116.5(2) . . ? C6 S1 C7 103.19(11) . . ? C19 S2 C20 103.39(12) . . ? C14 C28 H28A 109.5 . . ? C14 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C14 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C1 C27 H27A 109.5 . . ? C1 C27 H27B 109.5 . . ? C1 C27 H27C 109.5 . . ? #===END # Attachment '- co_crystal_Me_Br_9_1.cif' data_co_crystal_Me_Br_9_1 _database_code_depnum_ccdc_archive 'CCDC 801654' _audit_creation_date 2010-11-17T18:44:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; mixed crystal ; _chemical_formula_moiety 'C13.90 H15.70 Br0.10 O S' _chemical_formula_sum 'C13.90 H15.70 Br0.10 O S' _chemical_formula_weight 238.8 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M Pbca 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 15.5798(4) _cell_length_b 15.0633(4) _cell_length_c 20.6424(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4844.4(2) _cell_formula_units_Z 16 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 37467 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 29.92 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.46 _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2025.6 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.573 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_absorpt_correction_T_min 0.7269 _exptl_absorpt_correction_T_max 0.7526 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 103(2) _diffrn_radiation_probe X-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU RAXIS RAPID' _diffrn_measurement_method \w _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_unetI/netI 0.0331 _diffrn_reflns_number 53767 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 29.92 _diffrn_reflns_theta_full 29.92 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 6998 _reflns_number_gt 5748 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection RAPID-AUTO _computing_cell_refinement RAPID-AUTO _computing_data_reduction RAPID-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0437P)^2^+3.5398P] 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_number_reflns 6998 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1273 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_restrained_S_all 1.193 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.461 _refine_diff_density_min -1.142 _refine_diff_density_rms 0.065 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 -0.00713(11) 0.36094(12) 0.15829(9) 0.0237(3) Uani 1 1 d . . . H1 H -0.014 0.3622 0.1126 0.028 Uiso 1 1 calc R . . C2 C -0.07676(12) 0.37919(13) 0.19821(9) 0.0275(4) Uani 1 1 d . . . H2 H -0.1308 0.3934 0.1797 0.033 Uiso 1 1 calc R . . C3 C -0.06760(13) 0.37675(13) 0.26495(9) 0.0281(4) Uani 1 1 d . . . H3 H -0.1154 0.3884 0.2923 0.034 Uiso 1 1 calc R . . C4 C 0.01223(13) 0.35714(12) 0.29157(9) 0.0257(4) Uani 1 1 d . A . H4 H 0.0185 0.3558 0.3373 0.031 Uiso 1 1 calc R . . C5 C 0.08315(12) 0.33935(11) 0.25252(8) 0.0217(3) Uani 1 1 d . . . C6 C 0.07274(11) 0.34084(11) 0.18485(8) 0.0190(3) Uani 1 1 d . A . C7 C 0.13047(11) 0.34284(11) 0.05693(8) 0.0191(3) Uani 1 1 d . A . C8 C 0.10606(11) 0.28187(12) 0.01253(9) 0.0224(3) Uani 1 1 d . . . C9 C 0.08436(13) 0.30887(13) -0.05595(9) 0.0273(4) Uani 1 1 d . . . H9A H 0.0364 0.2715 -0.0716 0.033 Uiso 1 1 calc R . . H9B H 0.1346 0.2969 -0.084 0.033 Uiso 1 1 calc R . . C10 C 0.05938(12) 0.40573(13) -0.06308(9) 0.0272(4) Uani 1 1 d . . . H10A H 0.0021 0.4156 -0.0436 0.033 Uiso 1 1 calc R . . H10B H 0.0562 0.4214 -0.1096 0.033 Uiso 1 1 calc R . . C11 C 0.12531(12) 0.46432(12) -0.02955(8) 0.0232(3) Uani 1 1 d . . . H11A H 0.1804 0.4605 -0.0533 0.028 Uiso 1 1 calc R . . H11B H 0.1057 0.5268 -0.0313 0.028 Uiso 1 1 calc R . . C12 C 0.13982(11) 0.43844(12) 0.04003(8) 0.0200(3) Uani 1 1 d . . . C14 C 0.09813(15) 0.18447(13) 0.02571(11) 0.0357(5) Uani 1 1 d . . . H14A H 0.1279 0.17 0.0662 0.054 Uiso 1 1 calc R . . H14B H 0.1239 0.151 -0.01 0.054 Uiso 1 1 calc R . . H14C H 0.0373 0.1686 0.0296 0.054 Uiso 1 1 calc R . . C21 C -0.17131(12) 0.21413(12) 0.08845(8) 0.0230(3) Uani 1 1 d . . . H21 H -0.1777 0.2143 0.1342 0.028 Uiso 1 1 calc R . . C22 C -0.18316(13) 0.29214(12) 0.05360(9) 0.0247(4) Uani 1 1 d . . . H22 H -0.1987 0.3452 0.0756 0.03 Uiso 1 1 calc R . . C23 C -0.17229(12) 0.29284(12) -0.01330(9) 0.0248(4) Uani 1 1 d . . . H23 H -0.1792 0.3463 -0.0371 0.03 Uiso 1 1 calc R . . C24 C -0.15121(11) 0.21430(12) -0.04477(8) 0.0226(3) Uani 1 1 d . B . H24 H -0.1438 0.2148 -0.0905 0.027 Uiso 1 1 calc R . . C25 C -0.14076(12) 0.13525(14) -0.01131(10) 0.0291(3) Uani 1 1 d . . . C26 C -0.15005(11) 0.13574(11) 0.05650(8) 0.0195(3) Uani 1 1 d . B . C27 C -0.14124(11) 0.06441(11) 0.18074(8) 0.0200(3) Uani 1 1 d . B . C28 C -0.07215(11) 0.08783(11) 0.21632(9) 0.0220(3) Uani 1 1 d . . . C29 C -0.08041(12) 0.11019(12) 0.28704(9) 0.0262(4) Uani 1 1 d . . . H29A H -0.0397 0.1586 0.2976 0.031 Uiso 1 1 calc R . . H29B H -0.0639 0.0576 0.313 0.031 Uiso 1 1 calc R . . C30 C -0.16985(13) 0.13865(13) 0.30635(9) 0.0288(4) Uani 1 1 d . . . H30A H -0.1827 0.1976 0.2875 0.035 Uiso 1 1 calc R . . H30B H -0.1736 0.1435 0.3541 0.035 Uiso 1 1 calc R . . C31 C -0.23462(12) 0.07113(14) 0.28218(9) 0.0282(4) Uani 1 1 d . . . H31A H -0.2239 0.0132 0.3034 0.034 Uiso 1 1 calc R . . H31B H -0.2932 0.0907 0.294 0.034 Uiso 1 1 calc R . . C32 C -0.22880(12) 0.06017(12) 0.20953(8) 0.0230(3) Uani 1 1 d . . . C34 C 0.01708(13) 0.09508(14) 0.18997(13) 0.0379(5) Uani 1 1 d . . . H34A H 0.0209 0.0624 0.149 0.057 Uiso 1 1 calc R . . H34B H 0.0577 0.0699 0.2212 0.057 Uiso 1 1 calc R . . H34C H 0.031 0.1577 0.1825 0.057 Uiso 1 1 calc R . . O1 O 0.15979(10) 0.49338(9) 0.08052(7) 0.0326(3) Uani 1 1 d . . . O2 O -0.29255(10) 0.04890(12) 0.17650(7) 0.0409(4) Uani 1 1 d . . . S1 S 0.16323(3) 0.31267(3) 0.13653(2) 0.02367(11) Uani 1 1 d . . . S2 S -0.13282(4) 0.03384(3) 0.09788(2) 0.02965(12) Uani 1 1 d . . . C13 C 0.1684(5) 0.3151(7) 0.2842(5) 0.0293(14) Uani 0.9 1 d P A 1 H13A H 0.1663 0.33 0.3303 0.044 Uiso 0.9 1 calc PR A 1 H13B H 0.2149 0.3483 0.2634 0.044 Uiso 0.9 1 calc PR A 1 H13C H 0.1787 0.2513 0.2791 0.044 Uiso 0.9 1 calc PR A 1 C33 C -0.12950(16) 0.0451(2) -0.04787(17) 0.0291(3) Uani 0.9 1 d P B 1 H33A H -0.1301 0.0557 -0.0947 0.044 Uiso 0.9 1 calc PR B 1 H33B H -0.1767 0.005 -0.0363 0.044 Uiso 0.9 1 calc PR B 1 H33C H -0.0747 0.018 -0.0355 0.044 Uiso 0.9 1 calc PR B 1 Br1 Br 0.1871(5) 0.3196(6) 0.2888(4) 0.0253(9) Uani 0.1 1 d P A 2 Br2 Br -0.10398(14) 0.0501(2) -0.05187(14) 0.0291(3) Uani 0.1 1 d P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0230(8) 0.0278(9) 0.0204(8) -0.0010(7) -0.0006(6) 0.0015(7) C2 0.0213(9) 0.0334(10) 0.0278(9) -0.0045(8) 0.0005(7) 0.0020(7) C3 0.0274(9) 0.0310(9) 0.0258(9) -0.0061(7) 0.0073(7) 0.0007(7) C4 0.0343(10) 0.0237(8) 0.0192(8) -0.0017(7) 0.0024(7) -0.0003(7) C5 0.0260(9) 0.0174(7) 0.0218(8) 0.0015(6) -0.0018(7) 0.0005(6) C6 0.0214(8) 0.0152(7) 0.0203(7) 0.0014(6) 0.0014(6) 0.0001(6) C7 0.0180(8) 0.0212(8) 0.0180(7) 0.0019(6) 0.0017(6) 0.0023(6) C8 0.0182(8) 0.0227(8) 0.0264(8) -0.0024(7) 0.0034(6) 0.0004(6) C9 0.0250(9) 0.0331(10) 0.0237(8) -0.0082(7) -0.0011(7) -0.0028(7) C10 0.0265(9) 0.0369(10) 0.0182(8) -0.0001(7) -0.0033(7) 0.0043(8) C11 0.0299(9) 0.0244(8) 0.0152(7) 0.0022(6) 0.0020(6) 0.0027(7) C12 0.0213(8) 0.0206(8) 0.0181(7) -0.0008(6) 0.0009(6) 0.0026(6) C14 0.0378(11) 0.0238(9) 0.0454(12) -0.0021(9) 0.0055(9) -0.0068(8) C21 0.0307(9) 0.0216(8) 0.0168(7) 0.0010(6) 0.0033(6) -0.0016(7) C22 0.0322(10) 0.0200(8) 0.0220(8) 0.0011(7) -0.0005(7) -0.0022(7) C23 0.0317(10) 0.0216(8) 0.0210(8) 0.0059(7) -0.0040(7) -0.0042(7) C24 0.0226(8) 0.0291(9) 0.0160(7) 0.0032(7) -0.0013(6) -0.0023(7) C25 0.0206(8) 0.0370(6) 0.0299(5) 0.0037(4) 0.0045(6) -0.0010(6) C26 0.0206(8) 0.0191(8) 0.0188(7) 0.0029(6) 0.0018(6) -0.0002(6) C27 0.0273(8) 0.0183(7) 0.0144(7) 0.0031(6) 0.0010(6) 0.0010(6) C28 0.0226(8) 0.0137(7) 0.0297(9) 0.0058(6) 0.0002(7) 0.0017(6) C29 0.0288(9) 0.0229(8) 0.0268(9) 0.0026(7) -0.0120(7) -0.0040(7) C30 0.0406(11) 0.0291(9) 0.0167(8) -0.0008(7) -0.0026(7) 0.0025(8) C31 0.0241(9) 0.0420(11) 0.0186(8) 0.0037(8) 0.0022(6) -0.0014(8) C32 0.0237(8) 0.0272(8) 0.0182(7) 0.0048(7) -0.0034(6) -0.0039(7) C34 0.0232(9) 0.0289(10) 0.0615(14) 0.0077(10) 0.0088(9) -0.0011(8) O1 0.0530(9) 0.0234(7) 0.0213(6) -0.0039(5) -0.0060(6) -0.0015(6) O2 0.0300(8) 0.0634(11) 0.0291(7) 0.0071(7) -0.0118(6) -0.0148(7) S1 0.0206(2) 0.0308(2) 0.0195(2) 0.00666(17) 0.00167(15) 0.00711(17) S2 0.0530(3) 0.0196(2) 0.0164(2) 0.00203(16) 0.00518(19) 0.0073(2) C13 0.023(3) 0.044(2) 0.021(2) 0.0022(14) -0.0019(19) 0.001(2) C33 0.0206(8) 0.0370(6) 0.0299(5) 0.0037(4) 0.0045(6) -0.0010(6) Br1 0.021(2) 0.0338(16) 0.0209(14) 0.0020(11) -0.0063(16) 0.0044(17) Br2 0.0206(8) 0.0370(6) 0.0299(5) 0.0037(4) 0.0045(6) -0.0010(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.390(3) . ? C1 C6 1.393(2) . ? C1 H1 0.95 . ? C2 C3 1.385(3) . ? C2 H2 0.95 . ? C3 C4 1.391(3) . ? C3 H3 0.95 . ? C4 C5 1.394(3) . ? C4 H4 0.95 . ? C5 C6 1.406(2) . ? C5 C13 1.524(7) . ? C5 Br1 1.809(7) . ? C6 S1 1.7785(17) . ? C7 C8 1.352(2) . ? C7 C12 1.489(2) . ? C7 S1 1.7796(17) . ? C8 C14 1.497(3) . ? C8 C9 1.509(3) . ? C9 C10 1.517(3) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.521(3) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.505(2) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 O1 1.217(2) . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C21 C22 1.390(2) . ? C21 C26 1.392(2) . ? C21 H21 0.95 . ? C22 C23 1.391(3) . ? C22 H22 0.95 . ? C23 C24 1.389(3) . ? C23 H23 0.95 . ? C24 C25 1.386(3) . ? C24 H24 0.95 . ? C25 C26 1.407(3) . ? C25 Br2 1.636(4) . ? C25 C33 1.564(4) . ? C26 S2 1.7771(17) . ? C27 C28 1.350(2) . ? C27 C32 1.489(2) . ? C27 S2 1.7761(17) . ? C28 C34 1.497(3) . ? C28 C29 1.504(3) . ? C29 C30 1.512(3) . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C30 C31 1.517(3) . ? C30 H30A 0.99 . ? C30 H30B 0.99 . ? C31 C32 1.512(2) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C32 O2 1.217(2) . ? C34 H34A 0.98 . ? C34 H34B 0.98 . ? C34 H34C 0.98 . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C33 H33A 0.98 . ? C33 H33B 0.98 . ? C33 H33C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.45(16) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C3 C2 C1 120.26(18) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.36(17) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 121.40(17) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.68(16) . . ? C4 C5 C13 119.3(4) . . ? C6 C5 C13 122.0(4) . . ? C4 C5 Br1 120.1(3) . . ? C6 C5 Br1 121.1(3) . . ? C13 C5 Br1 4.6(7) . . ? C1 C6 C5 119.83(16) . . ? C1 C6 S1 122.63(13) . . ? C5 C6 S1 117.50(13) . . ? C8 C7 C12 121.72(15) . . ? C8 C7 S1 122.21(14) . . ? C12 C7 S1 115.80(12) . . ? C7 C8 C14 124.45(17) . . ? C7 C8 C9 120.99(16) . . ? C14 C8 C9 114.56(16) . . ? C8 C9 C10 114.04(15) . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C11 109.92(15) . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 112.67(15) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? O1 C12 C7 121.47(16) . . ? O1 C12 C11 121.18(16) . . ? C7 C12 C11 117.34(15) . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C22 C21 C26 120.21(16) . . ? C22 C21 H21 119.9 . . ? C26 C21 H21 119.9 . . ? C23 C22 C21 120.26(17) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 119.11(16) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C25 C24 C23 121.75(16) . . ? C25 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? C24 C25 C26 118.62(18) . . ? C24 C25 Br2 117.38(18) . . ? C26 C25 Br2 123.33(18) . . ? C24 C25 C33 121.3(2) . . ? C26 C25 C33 119.7(2) . . ? Br2 C25 C33 14.61(12) . . ? C21 C26 C25 120.01(16) . . ? C21 C26 S2 122.73(13) . . ? C25 C26 S2 117.26(14) . . ? C28 C27 C32 121.63(15) . . ? C28 C27 S2 122.20(14) . . ? C32 C27 S2 116.15(13) . . ? C27 C28 C34 124.18(18) . . ? C27 C28 C29 121.23(16) . . ? C34 C28 C29 114.58(17) . . ? C28 C29 C30 113.49(15) . . ? C28 C29 H29A 108.9 . . ? C30 C29 H29A 108.9 . . ? C28 C29 H29B 108.9 . . ? C30 C29 H29B 108.9 . . ? H29A C29 H29B 107.7 . . ? C29 C30 C31 109.65(16) . . ? C29 C30 H30A 109.7 . . ? C31 C30 H30A 109.7 . . ? C29 C30 H30B 109.7 . . ? C31 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? C32 C31 C30 111.08(15) . . ? C32 C31 H31A 109.4 . . ? C30 C31 H31A 109.4 . . ? C32 C31 H31B 109.4 . . ? C30 C31 H31B 109.4 . . ? H31A C31 H31B 108 . . ? O2 C32 C27 122.01(16) . . ? O2 C32 C31 121.49(17) . . ? C27 C32 C31 116.50(15) . . ? C28 C34 H34A 109.5 . . ? C28 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C28 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C6 S1 C7 103.27(8) . . ? C27 S2 C26 103.17(8) . . ? C5 C13 H13A 109.5 . . ? C5 C13 H13B 109.5 . . ? C5 C13 H13C 109.5 . . ? C25 C33 H33A 109.5 . . ? C25 C33 H33B 109.5 . . ? C25 C33 H33C 109.5 . . ? _chemical_name_common 'mixed crystal'