#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/36/2003628.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2003628 loop_ _publ_author_name 'Shaw, J. P.' 'Tan, E. W.' 'Blackman, A. G.' _publ_section_title ; Homochiral Methyl (S)-2-Benzenesulfonyloxy-4-bromo-4-methylpentanoate ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1411 _journal_page_last 1412 _journal_paper_doi 10.1107/S0108270195001818 _journal_volume 51 _journal_year 1995 _chemical_compound_source 'evaporation from hexane/dichloromethane' _chemical_formula_sum 'C13 H17 Br O5 S' _chemical_formula_weight 365.24 _chemical_name_systematic ; methyl (S)-2-benzenesulfonyloxy-4-bromo-4-methylpentanoate ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 104.89(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.352(2) _cell_length_b 7.1190(10) _cell_length_c 10.652(2) _cell_measurement_reflns_used 15 _cell_measurement_temperature 130(2) _cell_measurement_theta_max 17 _cell_measurement_theta_min 12 _cell_volume 758.6(3) _computing_cell_refinement SHELXTL-Plus _computing_data_collection 'SHELXTL-Plus (Sheldrick, 1991)' _computing_data_reduction SHELXTL-Plus _computing_molecular_graphics 'ORTEP (Johnson, 1965)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 130(2) _diffrn_measurement_device 'Nicolet R3M diffractometer' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 1520 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.98 _diffrn_standards_decay_% 2 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.862 _exptl_absorpt_correction_T_max 0.907 _exptl_absorpt_correction_T_min 0.590 _exptl_absorpt_correction_type 'empirical \y scans' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.599 _exptl_crystal_description block _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.615 _refine_diff_density_min -0.504 _refine_ls_abs_structure_details 'Flack (1983), \c = 0.01(2)' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_extinction_coef 0 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.050 _refine_ls_goodness_of_fit_obs 1.068 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 184 _refine_ls_number_reflns 1438 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.049 _refine_ls_restrained_S_obs 1.068 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_obs 0.0400 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.0000P] wh' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0898 _refine_ls_wR_factor_obs 0.0829 _reflns_number_observed 1214 _reflns_number_total 1438 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file ab1251.cif _[local]_cod_data_source_block tanz _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.0000P] wh' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.0000P] wh'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 758.6(2) _cod_database_code 2003628 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 Br1 0.0348(4) 0.0116(6) 0.0046(3) 0.0679(6) -0.0110(5) 0.0247(3) S1 0.0204(9) -0.0018(8) 0.0005(7) 0.0189(9) -0.0046(8) 0.0265(8) O1 0.020(2) -0.001(2) 0.000(2) 0.025(3) -0.002(2) 0.019(2) O2 0.015(2) 0.006(2) 0.003(2) 0.029(3) 0.005(2) 0.030(2) O3 0.016(2) 0.000(2) 0.001(2) 0.018(3) 0.000(2) 0.023(2) O4 0.019(3) -0.006(3) -0.007(2) 0.032(3) 0.003(3) 0.034(3) O5 0.041(3) -0.004(3) 0.010(2) 0.026(3) -0.008(3) 0.036(3) C1 0.052(5) -0.002(5) 0.012(4) 0.044(5) 0.007(4) 0.025(4) C2 0.028(4) -0.002(4) 0.001(3) 0.038(5) 0.003(3) 0.016(3) C3 0.025(4) 0.001(4) -0.001(3) 0.049(5) -0.005(3) 0.024(3) C4 0.023(4) -0.004(3) 0.004(3) 0.027(4) -0.003(3) 0.022(3) C5 0.018(3) -0.001(4) 0.003(2) 0.023(4) -0.001(4) 0.022(3) C6 0.020(3) 0.000(3) 0.010(2) 0.014(4) 0.007(3) 0.025(3) C7 0.034(4) -0.005(4) 0.005(3) 0.026(4) -0.001(3) 0.020(3) C8 0.018(3) -0.003(3) 0.001(3) 0.012(4) 0.002(3) 0.030(3) C9 0.018(3) -0.006(3) 0.004(3) 0.013(4) 0.002(3) 0.039(4) C10 0.027(4) -0.009(4) -0.012(3) 0.024(4) 0.013(4) 0.046(5) C11 0.051(5) -0.012(4) 0.005(4) 0.031(5) 0.002(4) 0.024(4) C12 0.047(5) -0.008(4) 0.015(4) 0.025(5) 0.003(4) 0.037(4) C13 0.029(4) 0.000(3) 0.007(3) 0.018(4) 0.008(3) 0.032(4) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol Br1 1 0.89489(7) 0.15280(14) 0.55164(6) 0.0430(3) Uani d . Br S1 1 0.5895(2) -0.0750(2) 0.8244(2) 0.0229(4) Uani d . S O1 1 0.7964(4) 0.2711(7) 1.0333(4) 0.0222(11) Uani d . O O2 1 0.9771(4) 0.1211(7) 1.0025(4) 0.0251(12) Uani d . O O3 1 0.6447(4) 0.1306(7) 0.8099(4) 0.0198(10) Uani d . O O4 1 0.4485(4) -0.0553(8) 0.7762(5) 0.0307(13) Uani d . O O5 1 0.6600(5) -0.2061(8) 0.7659(5) 0.0343(13) Uani d . O C1 1 0.7813(8) 0.5164(13) 0.5454(7) 0.040(2) Uani d . C H1A 1 0.7829(51) 0.5041(16) 0.4560(15) 0.060 Uiso calc R H H1B 1 0.8641(25) 0.5697(32) 0.5943(31) 0.060 Uiso calc R H H1C 1 0.7087(28) 0.5970(25) 0.5513(45) 0.060 Uiso calc R H C2 1 0.7624(7) 0.3239(12) 0.6000(6) 0.028(2) Uani d . C C3 1 0.6267(6) 0.2451(12) 0.5387(6) 0.034(2) Uani d . C H3A 1 0.6105(22) 0.2491(66) 0.4459(6) 0.051 Uiso calc R H H3B 1 0.5601(7) 0.3184(44) 0.5647(40) 0.051 Uiso calc R H H3C 1 0.6224(17) 0.1174(25) 0.5662(38) 0.051 Uiso calc R H C4 1 0.7995(7) 0.3369(11) 0.7479(6) 0.024(2) Uani d . C H4A 1 0.8912(7) 0.3805(11) 0.7764(6) 0.029 Uiso calc R H H4B 1 0.7435(7) 0.4322(11) 0.7723(6) 0.029 Uiso calc R H C5 1 0.7873(5) 0.1597(13) 0.8217(5) 0.0212(13) Uani d . C H5 1 0.8227(5) 0.0534(13) 0.7824(5) 0.025 Uiso calc R H C6 1 0.8659(6) 0.1800(11) 0.9635(5) 0.0189(14) Uani d . C C7 1 0.8637(7) 0.2963(12) 1.1696(6) 0.027(2) Uani d . C H7A 1 0.8039(16) 0.3552(54) 1.2132(10) 0.040 Uiso calc R H H7B 1 0.9411(25) 0.3742(49) 1.1774(6) 0.040 Uiso calc R H H7C 1 0.8908(36) 0.1762(13) 1.2085(11) 0.040 Uiso calc R H C8 1 0.6309(6) -0.1103(9) 0.9921(6) 0.021(2) Uani d . C C9 1 0.7515(6) -0.1997(10) 1.0527(7) 0.024(2) Uani d . C H9 1 0.8071(6) -0.2488(10) 1.0048(7) 0.029 Uiso calc R H C10 1 0.7843(7) -0.2118(12) 1.1874(7) 0.037(2) Uani d . C H10 1 0.8639(7) -0.2692(12) 1.2310(7) 0.044 Uiso calc R H C11 1 0.7013(8) -0.1408(11) 1.2567(7) 0.036(2) Uani d . C H11 1 0.7257(8) -0.1499(11) 1.3468(7) 0.043 Uiso calc R H C12 1 0.5830(8) -0.0564(12) 1.1960(7) 0.035(2) Uani d . C H12 1 0.5274(8) -0.0094(12) 1.2447(7) 0.042 Uiso calc R H C13 1 0.5467(7) -0.0415(10) 1.0631(6) 0.026(2) Uani d . C H13 1 0.4660(7) 0.0145(10) 1.0211(6) 0.032 Uiso calc R H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001 H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006 S S 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1246 0.123 Br Br 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' -0.2901 2. loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O5 S1 O4 120.0(3) yes O5 S1 O3 108.8(3) yes O4 S1 O3 103.6(3) yes O5 S1 C8 109.6(3) yes O4 S1 C8 110.0(3) yes O3 S1 C8 103.4(3) yes C6 O1 C7 115.4(5) yes C5 O3 S1 120.0(5) yes C3 C2 C1 111.7(6) yes C3 C2 C4 115.6(6) yes C1 C2 C4 108.5(6) yes C3 C2 Br1 106.8(5) yes C1 C2 Br1 106.7(5) yes C4 C2 Br1 107.2(5) yes C5 C4 C2 117.1(6) yes O3 C5 C4 106.9(5) yes O3 C5 C6 111.6(4) yes C4 C5 C6 110.0(6) yes O2 C6 O1 126.1(5) yes O2 C6 C5 122.1(6) yes O1 C6 C5 111.8(5) yes C13 C8 C9 121.4(6) yes C13 C8 S1 119.1(5) yes C9 C8 S1 119.5(5) yes C10 C9 C8 117.1(7) yes C11 C10 C9 121.0(7) yes C10 C11 C12 121.2(7) yes C11 C12 C13 119.7(8) yes C12 C13 C8 119.5(7) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C2 1.999(8) yes S1 O5 1.424(5) yes S1 O4 1.424(5) yes S1 O3 1.593(5) yes S1 C8 1.745(6) yes O1 C6 1.329(8) yes O1 C7 1.452(7) yes O2 C6 1.195(7) yes O3 C5 1.464(6) yes C1 C2 1.521(12) yes C2 C3 1.497(9) yes C2 C4 1.526(9) yes C4 C5 1.509(11) yes C5 C6 1.527(7) yes C8 C13 1.383(9) yes C8 C9 1.402(9) yes C9 C10 1.390(9) yes C10 C11 1.365(11) yes C11 C12 1.368(11) yes C12 C13 1.372(10) yes