#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/48/2234899.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_2234899
loop_
_publ_author_name
'Liu, Fei'
'Ren, Shi-Ying'
'Yang, Wei-Ji'
_publ_section_title
;
 2-Bromo-2-methyl-1-[4-(methylsulfanyl)phenyl]propan-1-one
;
_journal_coeditor_code           BG2458
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1759
_journal_paper_doi               10.1107/S1600536812021472
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H13 Br O S'
_chemical_formula_moiety         'C11 H13 Br O S'
_chemical_formula_sum            'C11 H13 Br O S'
_chemical_formula_weight         273.18
_chemical_name_systematic
;
2-Bromo-2-methyl-1-[4-(methylsulfanyl)phenyl]propan-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.638(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.061(3)
_cell_length_b                   7.120(2)
_cell_length_c                   14.721(4)
_cell_measurement_reflns_used    4327
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.992
_cell_measurement_theta_min      2.170
_cell_volume                     1149.1(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2008)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'publCIF (Westrip, 2010) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku  AFC10/Saturn724+'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9900
_diffrn_reflns_theta_full        31.01
_diffrn_reflns_theta_max         31.01
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.725
_exptl_absorpt_correction_T_max  0.5505
_exptl_absorpt_correction_T_min  0.4329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.720
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                2901
_reflns_number_total             3625
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2458.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2234899
_cod_database_fobs_code          2234899
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'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
Br Br1 0.327247(17) 0.69311(3) 0.037381(13) 0.03062(7) Uani d . 1 1
S S1 0.86419(4) 0.48317(6) 0.36691(3) 0.02352(10) Uani d . 1 1
O O1 0.25965(11) 0.5378(2) 0.26208(9) 0.0358(3) Uani d . 1 1
C C1 0.71222(15) 0.4889(2) 0.31441(12) 0.0184(3) Uani d . 1 1
C C2 0.62070(15) 0.4850(2) 0.37198(12) 0.0211(3) Uani d . 1 1
H H2 0.6426 0.4798 0.4366 0.025 Uiso calc R 1 1
C C3 0.49965(15) 0.4886(2) 0.33555(12) 0.0213(3) Uani d . 1 1
H H3 0.4389 0.4856 0.3755 0.026 Uiso calc R 1 1
C C4 0.46416(15) 0.4968(2) 0.24059(11) 0.0186(3) Uani d . 1 1
C C5 0.55563(15) 0.5004(2) 0.18392(12) 0.0201(3) Uani d . 1 1
H H5 0.5339 0.5061 0.1193 0.024 Uiso calc R 1 1
C C6 0.67786(16) 0.4957(2) 0.22041(12) 0.0212(3) Uani d . 1 1
H H6 0.7387 0.4972 0.1805 0.025 Uiso calc R 1 1
C C7 0.94956(16) 0.4878(3) 0.27138(13) 0.0256(4) Uani d . 1 1
H H7A 0.9245 0.3824 0.2303 0.031 Uiso calc R 1 1
H H7B 1.0368 0.4773 0.2937 0.031 Uiso calc R 1 1
H H7C 0.9340 0.6063 0.2380 0.031 Uiso calc R 1 1
C C8 0.33064(16) 0.5063(2) 0.20746(12) 0.0214(4) Uani d . 1 1
C C9 0.27806(15) 0.4717(2) 0.10720(12) 0.0213(4) Uani d . 1 1
C C10 0.13996(16) 0.4720(3) 0.09560(14) 0.0325(4) Uani d . 1 1
H H10A 0.1084 0.4581 0.0305 0.039 Uiso calc R 1 1
H H10B 0.1110 0.5908 0.1185 0.039 Uiso calc R 1 1
H H10C 0.1111 0.3673 0.1303 0.039 Uiso calc R 1 1
C C11 0.32472(17) 0.2949(2) 0.06566(13) 0.0264(4) Uani d . 1 1
H H11A 0.3003 0.1846 0.0987 0.032 Uiso calc R 1 1
H H11B 0.4139 0.2998 0.0705 0.032 Uiso calc R 1 1
H H11C 0.2900 0.2861 0.0010 0.032 Uiso calc R 1 1
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
Br1 0.03163(12) 0.03130(13) 0.02925(11) 0.00122(8) 0.00520(8) 0.00951(8)
S1 0.0197(2) 0.0277(2) 0.0229(2) 0.00113(17) 0.00177(16) -0.00186(17)
O1 0.0213(7) 0.0622(10) 0.0251(7) 0.0015(7) 0.0078(5) -0.0100(7)
C1 0.0189(8) 0.0163(8) 0.0201(8) 0.0003(6) 0.0028(6) -0.0008(6)
C2 0.0234(9) 0.0247(9) 0.0155(8) 0.0015(7) 0.0036(6) -0.0007(6)
C3 0.0230(8) 0.0229(9) 0.0194(8) 0.0001(7) 0.0077(6) -0.0014(7)
C4 0.0193(8) 0.0178(8) 0.0193(8) 0.0004(6) 0.0054(6) -0.0005(6)
C5 0.0213(8) 0.0240(9) 0.0158(8) -0.0008(7) 0.0060(6) -0.0001(6)
C6 0.0218(8) 0.0230(9) 0.0204(8) -0.0011(7) 0.0085(6) 0.0001(7)
C7 0.0187(8) 0.0266(10) 0.0323(10) -0.0008(7) 0.0063(7) 0.0006(8)
C8 0.0207(8) 0.0234(9) 0.0209(8) 0.0004(7) 0.0058(6) -0.0006(7)
C9 0.0199(8) 0.0253(9) 0.0192(8) -0.0021(7) 0.0047(6) 0.0019(7)
C10 0.0189(9) 0.0487(13) 0.0294(10) -0.0018(8) 0.0018(7) 0.0004(9)
C11 0.0278(10) 0.0273(11) 0.0244(9) -0.0048(7) 0.0045(7) -0.0039(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C7 103.15(9)
C6 C1 C2 118.63(16)
C6 C1 S1 124.05(13)
C2 C1 S1 117.32(13)
C3 C2 C1 120.47(16)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 121.25(15)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 117.90(16)
C5 C4 C8 124.62(16)
C3 C4 C8 117.45(14)
C6 C5 C4 121.01(16)
C6 C5 H5 119.5
C4 C5 H5 119.5
C1 C6 C5 120.74(15)
C1 C6 H6 119.6
C5 C6 H6 119.6
S1 C7 H7A 109.5
S1 C7 H7B 109.5
H7A C7 H7B 109.5
S1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O1 C8 C4 119.29(16)
O1 C8 C9 118.05(16)
C4 C8 C9 122.63(14)
C10 C9 C11 110.31(15)
C10 C9 C8 110.88(14)
C11 C9 C8 114.50(15)
C10 C9 Br1 106.31(12)
C11 C9 Br1 108.46(12)
C8 C9 Br1 105.95(11)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9 1.9962(17)
S1 C1 1.7548(17)
S1 C7 1.7954(19)
O1 C8 1.217(2)
C1 C6 1.386(2)
C1 C2 1.404(2)
C2 C3 1.375(2)
C2 H2 0.9500
C3 C4 1.402(2)
C3 H3 0.9500
C4 C5 1.395(2)
C4 C8 1.494(2)
C5 C6 1.387(2)
C5 H5 0.9500
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.533(2)
C9 C10 1.514(2)
C9 C11 1.520(2)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C11 H11A O1 2_545 0.98 2.47 3.359(2) 150 yes
C5 H5 Br1 . 0.95 2.78 3.387(2) 123 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
C7 S1 C1 C6 -0.14(17)
C7 S1 C1 C2 179.45(13)
C6 C1 C2 C3 -0.2(3)
S1 C1 C2 C3 -179.84(13)
C1 C2 C3 C4 -0.2(3)
C2 C3 C4 C5 0.2(3)
C2 C3 C4 C8 -178.13(15)
C3 C4 C5 C6 0.1(2)
C8 C4 C5 C6 178.36(16)
C2 C1 C6 C5 0.6(3)
S1 C1 C6 C5 -179.83(13)
C4 C5 C6 C1 -0.5(3)
C5 C4 C8 O1 -166.18(16)
C3 C4 C8 O1 12.1(2)
C5 C4 C8 C9 15.8(3)
C3 C4 C8 C9 -165.99(15)
O1 C8 C9 C10 -3.6(2)
C4 C8 C9 C10 174.51(16)
O1 C8 C9 C11 -129.15(17)
C4 C8 C9 C11 48.9(2)
O1 C8 C9 Br1 111.37(16)
C4 C8 C9 Br1 -70.55(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9634825
