#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200514.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_2200514 loop_ _publ_author_name 'Robinson, Paul D.' 'Parady, Thomas E.' 'Hou, Yuqing' 'Meyers, Cal Y.' _publ_section_title ; 2-Bromo-2-propyl phenyl sulfone ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o584 _journal_page_last o586 _journal_paper_doi 10.1107/S1600536801007516 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C9 H11 Br1 O2 S1' _chemical_formula_moiety 'C9 H11 Br1 O2 S1' _chemical_formula_sum 'C9 H11 Br O2 S' _chemical_formula_weight 263.15 _chemical_melting_point 419.5(5) _chemical_name_systematic ; \a-bromoisopropyl phenyl sulfone ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 21.134(2) _cell_length_b 6.2537(11) _cell_length_c 7.979(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 14.6 _cell_measurement_theta_min 12.5 _cell_volume 1054.6(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,1996) ; _computing_data_reduction 'PROCESS in TEXSAN (Molecular Structure Corporation, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1965) in TEXSAN' _computing_publication_material 'TEXSAN, SHELXL97, and PLATON (Spek, 2000)' _computing_structure_refinement 'LS in TEXSAN and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Burla et al., 1989)' _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Rigaku AFC-5S' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .043 _diffrn_reflns_av_sigmaI/netI .046 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1917 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 1.93 _diffrn_standards_decay_% 3.2 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 4.061 _exptl_absorpt_correction_T_max .544 _exptl_absorpt_correction_T_min .398 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 528 _exptl_crystal_size_max .36 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .15 _refine_diff_density_max .31 _refine_diff_density_min -.27 _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel opposites, wR(F^2^) (inverse) 0.097' _refine_ls_abs_structure_Flack .09(2) _refine_ls_extinction_coef .0094(15) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 121 _refine_ls_number_reflns 1008 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.005 _refine_ls_R_factor_all .073 _refine_ls_R_factor_gt .034 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.1257P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .094 _reflns_number_gt 668 _reflns_number_total 1008 _reflns_threshold_expression I>2\s(I) _cod_data_source_file om6024.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '419-420' was changed to '419.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '419-420' was changed to '419.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 1054.6(4) _cod_original_formula_sum 'C9 H11 Br1 O2 S1' _cod_database_code 2200514 _cod_database_fobs_code 2200514 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Br .34405(4) .11425(18) .95490(9) .0798(5) Uani d . 1 . . Br S1 .35712(9) .1208(3) .5784(3) .0510(5) Uani d . 1 . . S O1 .3573(3) -.1059(8) .5880(12) .086(2) Uani d . 1 . . O O2 .3329(3) .2233(11) .4315(8) .0718(17) Uani d . 1 . . O C1 .4349(3) .2101(12) .6120(9) .0451(18) Uani d . 1 . . C C2 .4779(4) .0770(15) .6900(13) .065(2) Uani d . 1 . . C C3 .5415(4) .1520(19) .7061(13) .081(3) Uani d . 1 . . C C4 .5577(4) .3453(18) .6416(12) .073(3) Uani d . 1 . . C C5 .5150(4) .4728(16) .5649(14) .076(3) Uani d . 1 . . C C6 .4542(4) .4064(12) .5477(11) .057(2) Uani d . 1 . . C C7 .3092(3) .2238(13) .7476(9) .0473(19) Uani d . 1 . . C C8 .2421(3) .1324(12) .7296(10) .062(3) Uani d . 1 . . C C9 .3116(4) .4693(11) .7572(12) .0539(19) Uani d . 1 . . C H2 .4659 -.0564 .7306 .078 Uiso calc R 1 . . H H3 .5717 .0688 .7605 .097 Uiso calc R 1 . . H H4 .5994 .3913 .6505 .088 Uiso calc R 1 . . H H5 .5272 .6058 .5239 .091 Uiso calc R 1 . . H H6 .4251 .4929 .4924 .068 Uiso calc R 1 . . H H8a .2158 .1871 .8178 .092 Uiso calc R 1 . . H H8b .2436 -.0207 .7365 .092 Uiso calc R 1 . . H H8c .2248 .1739 .6231 .092 Uiso calc R 1 . . H H9a .2808 .5188 .8366 .081 Uiso calc R 1 . . H H9b .3025 .5284 .6489 .081 Uiso calc R 1 . . H H9c .3530 .5137 .7923 .081 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br .0675(5) .1134(10) .0587(6) -.0113(6) -.0062(6) .0336(6) S1 .0518(11) .0469(13) .0542(13) -.0083(10) .0028(9) -.0053(10) O1 .089(4) .047(3) .123(6) -.012(3) .024(4) -.021(4) O2 .063(3) .105(4) .047(4) .006(3) -.013(3) .000(4) C1 .044(4) .048(5) .044(4) .006(3) -.001(4) .003(4) C2 .060(5) .069(7) .066(5) .025(5) .011(5) .004(4) C3 .055(5) .133(10) .055(5) .038(6) .007(4) .013(6) C4 .045(5) .104(8) .070(6) -.008(5) .009(4) -.011(6) C5 .056(5) .074(6) .097(7) -.006(5) .015(6) .014(6) C6 .050(4) .055(5) .065(5) .000(4) .001(4) .009(4) C7 .040(4) .058(5) .044(4) -.007(4) -.005(3) .007(4) C8 .040(4) .087(6) .058(6) -.018(4) -.003(4) .005(4) C9 .052(5) .047(4) .063(5) .006(4) .009(4) .001(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -1 2 0 -2 1 0 -3 1 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 O1 S1 O2 119.5(5) no O1 S1 C1 107.8(4) no O2 S1 C1 108.5(3) no O1 S1 C7 108.5(4) no O2 S1 C7 104.6(3) no C1 S1 C7 107.3(3) no C2 C1 C6 120.4(7) no C2 C1 S1 119.5(6) no C6 C1 S1 119.9(6) no C1 C2 C3 117.5(9) no C4 C3 C2 119.7(9) no C5 C4 C3 121.9(9) no C4 C5 C6 119.8(9) no C4 C5 H5 120.1 no C5 C6 C1 120.7(8) no C8 C7 C9 113.9(7) no C8 C7 S1 108.4(5) no C9 C7 S1 112.0(5) no C8 C7 Br 107.4(5) no C9 C7 Br 107.4(6) no S1 C7 Br 107.5(4) no C1 C2 H2 121.3 no C3 C2 H2 121.3 no C4 C3 H3 120.2 no C2 C3 H3 120.2 no C5 C4 H4 119.0 no C3 C4 H4 119.0 no C6 C5 H5 120.1 no C5 C6 H6 119.7 no C1 C6 H6 119.7 no C7 C8 H8a 109.5 no C7 C8 H8b 109.5 no H8a C8 H8b 109.5 no C7 C8 H8c 109.5 no H8a C8 H8c 109.5 no H8b C8 H8c 109.5 no C7 C9 H9a 109.5 no C7 C9 H9b 109.5 no H9a C9 H9b 109.5 no C7 C9 H9c 109.5 no H9a C9 H9c 109.5 no H9b C9 H9c 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br C7 . 1.935(7) no S1 O1 . 1.420(5) no S1 O2 . 1.431(7) no S1 C1 . 1.757(7) no S1 C7 . 1.806(8) no C1 C2 . 1.381(11) no C1 C6 . 1.391(10) no C2 C3 . 1.429(14) no C3 C4 . 1.358(12) no C4 C5 . 1.351(13) no C5 C6 . 1.357(11) no C7 C8 . 1.537(9) no C7 C9 . 1.538(11) no C2 H2 . .9300 no C3 H3 . .9300 no C4 H4 . .9300 no C5 H5 . .9300 no C6 H6 . .9300 no C8 H8a . .9600 no C8 H8b . .9600 no C8 H8c . .9600 no C9 H9a . .9600 no C9 H9b . .9600 no C9 H9c . .9600 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag C6 C9 3.469(12) . yes Br C2 3.539(9) . yes O1 C9 3.133(10) 1_545 yes O2 C8 3.414(10) 3_554 yes Br C3 3.555(10) 2_655 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag O1 S1 C1 C2 -19.8(8) no O2 S1 C1 C2 -150.6(7) no C7 S1 C1 C2 96.9(7) no O1 S1 C1 C6 154.9(7) no O2 S1 C1 C6 24.1(7) no C7 S1 C1 C6 -88.4(7) no C6 C1 C2 C3 1.9(13) no S1 C1 C2 C3 176.6(7) no C1 C2 C3 C4 -1.7(14) no C2 C3 C4 C5 1.4(15) no C3 C4 C5 C6 -1.3(15) no C4 C5 C6 C1 1.6(14) no C2 C1 C6 C5 -1.9(13) no S1 C1 C6 C5 -176.6(7) no O1 S1 C7 C8 -59.1(6) no O2 S1 C7 C8 69.6(6) no C1 S1 C7 C8 -175.3(5) no O1 S1 C7 C9 174.4(6) no O2 S1 C7 C9 -57.0(6) no C1 S1 C7 C9 58.2(6) no O1 S1 C7 Br 56.7(5) no O2 S1 C7 Br -174.6(4) no C1 S1 C7 Br -59.5(4) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21132811 2 PubChem 85788267