#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/92/2239216.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_2239216
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-2,4,6-trimethyl-3-(3-methylphenylsulfinyl)-1-benzofuran
;
_journal_coeditor_code           BX2455
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o435
_journal_paper_doi               10.1107/S1600536814005352
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C18 H17 Br O2 S'
_chemical_formula_moiety         'C18 H17 Br O2 S'
_chemical_formula_sum            'C18 H17 Br O2 S'
_chemical_formula_weight         377.29
_chemical_melting_point_gt       469
_chemical_melting_point_lt       470
_chemical_name_systematic
;
5-Bromo-2,4,6-trimethyl-3-(3-methylphenylsulfinyl)-1-benzofuran
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form.cif (version 2.0)'
_cell_angle_alpha                69.3840(10)
_cell_angle_beta                 76.4210(10)
_cell_angle_gamma                76.7990(10)
_cell_formula_units_Z            2
_cell_length_a                   6.23360(10)
_cell_length_b                   11.0353(2)
_cell_length_c                   12.9149(2)
_cell_measurement_reflns_used    8866
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      3.01
_cell_volume                     797.84(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and
DIAMOND (Brandenburg, 1998)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graphite multilayer'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14962
_diffrn_reflns_theta_full        28.44
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         1.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.711
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.492
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0260
_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)+(0.0354P)²+0.3061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0697
_reflns_number_gt                3702
_reflns_number_total             4023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2455sup1.cif
_cod_data_source_block           I
_cod_database_code               2239216
_cod_database_fobs_code          2239216
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.62873(3) 0.900826(16) 0.403993(14) 0.03223(7) Uani d . 1 2
S S1 0.75692(6) 0.51077(3) 0.11568(3) 0.01987(9) Uani d . 1 2
O O1 0.27755(19) 0.45708(11) 0.37436(9) 0.0241(2) Uani d . 1 2
O O2 0.99335(19) 0.51170(11) 0.12084(10) 0.0265(2) Uani d . 1 2
C C1 0.5810(3) 0.51004(14) 0.24439(12) 0.0196(3) Uani d . 1 2
C C2 0.5305(2) 0.59855(14) 0.31119(12) 0.0190(3) Uani d . 1 2
C C3 0.6265(3) 0.69926(14) 0.31564(12) 0.0195(3) Uani d . 1 2
C C4 0.5100(3) 0.76127(15) 0.39418(13) 0.0219(3) Uani d . 1 2
C C5 0.3111(3) 0.72874(16) 0.46735(13) 0.0244(3) Uani d . 1 2
C C6 0.2268(3) 0.62354(17) 0.46533(13) 0.0252(3) Uani d . 1 2
H H6 0.0964 0.5954 0.5154 0.030 Uiso calc R 1 2
C C7 0.3399(3) 0.56176(15) 0.38791(12) 0.0214(3) Uani d . 1 2
C C8 0.4262(3) 0.42809(15) 0.28649(12) 0.0221(3) Uani d . 1 2
C C9 0.8457(3) 0.73299(16) 0.24263(14) 0.0242(3) Uani d . 1 2
H H9A 0.8171 0.8110 0.1782 0.036 Uiso calc R 1 2
H H9B 0.9253 0.6592 0.2159 0.036 Uiso calc R 1 2
H H9C 0.9372 0.7506 0.2863 0.036 Uiso calc R 1 2
C C10 0.1860(3) 0.80420(19) 0.54665(16) 0.0341(4) Uani d . 1 2
H H10A 0.0587 0.7619 0.5938 0.051 Uiso calc R 1 2
H H10B 0.1318 0.8943 0.5033 0.051 Uiso calc R 1 2
H H10C 0.2863 0.8054 0.5943 0.051 Uiso calc R 1 2
C C11 0.3854(3) 0.31944(16) 0.25548(14) 0.0270(3) Uani d . 1 2
H H11A 0.2470 0.3462 0.2240 0.041 Uiso calc R 1 2
H H11B 0.3713 0.2422 0.3224 0.041 Uiso calc R 1 2
H H11C 0.5108 0.2979 0.1995 0.041 Uiso calc R 1 2
C C12 0.6482(3) 0.67448(14) 0.03546(12) 0.0198(3) Uani d . 1 2
C C13 0.7999(3) 0.75067(15) -0.04158(12) 0.0225(3) Uani d . 1 2
H H13 0.9557 0.7183 -0.0474 0.027 Uiso calc R 1 2
C C14 0.7230(3) 0.87472(16) -0.11039(14) 0.0275(3) Uani d . 1 2
C C15 0.4952(3) 0.92001(17) -0.09772(15) 0.0329(4) Uani d . 1 2
H H15 0.4411 1.0057 -0.1425 0.039 Uiso calc R 1 2
C C16 0.3449(3) 0.84324(19) -0.02136(15) 0.0337(4) Uani d . 1 2
H H16 0.1893 0.8765 -0.0144 0.040 Uiso calc R 1 2
C C17 0.4195(3) 0.71802(17) 0.04509(14) 0.0272(3) Uani d . 1 2
H H17 0.3168 0.6635 0.0959 0.033 Uiso calc R 1 2
C C18 0.8835(4) 0.9564(2) -0.19860(17) 0.0443(5) Uani d . 1 2
H H18A 0.8480 0.9733 -0.2729 0.066 Uiso calc R 1 2
H H18B 1.0366 0.9092 -0.1953 0.066 Uiso calc R 1 2
H H18C 0.8703 1.0399 -0.1850 0.066 Uiso calc R 1 2
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_site_symmetry_3
_geom_angle
O2 S1 C1 . 111.08(7)
O2 S1 C12 . 106.70(7)
C1 S1 C12 . 96.91(7)
O2 S1 O2 2_765 78.25(6)
C1 S1 O2 2_765 169.73(6)
C12 S1 O2 2_765 83.97(5)
C8 O1 C7 . 106.60(12)
C8 C1 C2 . 107.12(13)
C8 C1 S1 . 118.68(12)
C2 C1 S1 . 133.04(11)
C7 C2 C3 . 119.45(14)
C7 C2 C1 . 104.27(13)
C3 C2 C1 . 136.25(14)
C4 C3 C2 . 115.39(14)
C4 C3 C9 . 123.20(13)
C2 C3 C9 . 121.37(13)
C3 C4 C5 . 125.00(14)
C3 C4 Br1 . 117.82(11)
C5 C4 Br1 . 117.18(11)
C6 C5 C4 . 118.23(14)
C6 C5 C10 . 119.23(15)
C4 C5 C10 . 122.54(15)
C7 C6 C5 . 117.29(14)
C7 C6 H6 . 121.4
C5 C6 H6 . 121.4
C6 C7 O1 . 124.56(14)
C6 C7 C2 . 124.45(14)
O1 C7 C2 . 110.98(13)
C1 C8 O1 . 110.99(13)
C1 C8 C11 . 133.49(15)
O1 C8 C11 . 115.50(14)
C3 C9 H9A . 109.5
C3 C9 H9B . 109.5
H9A C9 H9B . 109.5
C3 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C5 C10 H10A . 109.5
C5 C10 H10B . 109.5
H10A C10 H10B . 109.5
C5 C10 H10C . 109.5
H10A C10 H10C . 109.5
H10B C10 H10C . 109.5
C8 C11 H11A . 109.5
C8 C11 H11B . 109.5
H11A C11 H11B . 109.5
C8 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
C13 C12 C17 . 121.63(14)
C13 C12 S1 . 117.57(12)
C17 C12 S1 . 120.62(12)
C12 C13 C14 . 119.71(15)
C12 C13 H13 . 120.1
C14 C13 H13 . 120.1
C15 C14 C13 . 118.57(16)
C15 C14 C18 . 120.73(16)
C13 C14 C18 . 120.69(17)
C16 C15 C14 . 121.38(16)
C16 C15 H15 . 119.3
C14 C15 H15 . 119.3
C15 C16 C17 . 120.44(17)
C15 C16 H16 . 119.8
C17 C16 H16 . 119.8
C16 C17 C12 . 118.19(16)
C16 C17 H17 . 120.9
C12 C17 H17 . 120.9
C14 C18 H18A . 109.5
C14 C18 H18B . 109.5
H18A C18 H18B . 109.5
C14 C18 H18C . 109.5
H18A C18 H18C . 109.5
H18B C18 H18C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C4 . 1.9073(15)
S1 O2 . 1.4934(12)
S1 C1 . 1.7619(15)
S1 C12 . 1.8024(15)
S1 O2 2_765 3.1527(12)
O1 C8 . 1.3694(19)
O1 C7 . 1.3770(18)
C1 C8 . 1.361(2)
C1 C2 . 1.457(2)
C2 C7 . 1.393(2)
C2 C3 . 1.401(2)
C3 C4 . 1.393(2)
C3 C9 . 1.508(2)
C4 C5 . 1.405(2)
C5 C6 . 1.390(2)
C5 C10 . 1.510(2)
C6 C7 . 1.375(2)
C6 H6 . 0.9500
C8 C11 . 1.479(2)
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
C11 H11A . 0.9800
C11 H11B . 0.9800
C11 H11C . 0.9800
C12 C13 . 1.387(2)
C12 C17 . 1.387(2)
C13 C14 . 1.392(2)
C13 H13 . 0.9500
C14 C15 . 1.385(3)
C14 C18 . 1.505(2)
C15 C16 . 1.381(3)
C15 H15 . 0.9500
C16 C17 . 1.386(2)
C16 H16 . 0.9500
C17 H17 . 0.9500
C18 H18A . 0.9800
C18 H18B . 0.9800
C18 H18C . 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
C6 H6 O1 2_566 0.95 2.50 3.4478(19) 171.8
C11 H11A O2 1_455 0.98 2.36 3.244(2) 149.8
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
O2 S1 C1 C8 -136.06(12)
C12 S1 C1 C8 113.02(13)
O2 S1 C1 C2 58.06(17)
C12 S1 C1 C2 -52.85(16)
C8 C1 C2 C7 -1.46(16)
S1 C1 C2 C7 165.60(13)
C8 C1 C2 C3 176.62(17)
S1 C1 C2 C3 -16.3(3)
C7 C2 C3 C4 -4.3(2)
C1 C2 C3 C4 177.88(16)
C7 C2 C3 C9 173.53(14)
C1 C2 C3 C9 -4.3(3)
C2 C3 C4 C5 0.9(2)
C9 C3 C4 C5 -176.88(15)
C2 C3 C4 Br1 -179.31(10)
C9 C3 C4 Br1 2.9(2)
C3 C4 C5 C6 2.7(2)
Br1 C4 C5 C6 -177.13(12)
C3 C4 C5 C10 -176.77(15)
Br1 C4 C5 C10 3.4(2)
C4 C5 C6 C7 -2.7(2)
C10 C5 C6 C7 176.80(15)
C5 C6 C7 O1 -179.40(14)
C5 C6 C7 C2 -0.8(2)
C8 O1 C7 C6 177.44(15)
C8 O1 C7 C2 -1.35(16)
C3 C2 C7 C6 4.5(2)
C1 C2 C7 C6 -177.07(15)
C3 C2 C7 O1 -176.74(13)
C1 C2 C7 O1 1.73(16)
C2 C1 C8 O1 0.71(17)
S1 C1 C8 O1 -168.54(10)
C2 C1 C8 C11 179.18(16)
S1 C1 C8 C11 9.9(2)
C7 O1 C8 C1 0.35(17)
C7 O1 C8 C11 -178.42(13)
O2 S1 C12 C13 25.77(14)
C1 S1 C12 C13 140.27(12)
O2 S1 C12 C17 -158.95(13)
C1 S1 C12 C17 -44.45(14)
C17 C12 C13 C14 0.8(2)
S1 C12 C13 C14 176.07(12)
C12 C13 C14 C15 1.6(2)
C12 C13 C14 C18 -176.88(16)
C13 C14 C15 C16 -2.1(3)
C18 C14 C15 C16 176.39(18)
C14 C15 C16 C17 0.1(3)
C15 C16 C17 C12 2.3(3)
C13 C12 C17 C16 -2.8(2)
S1 C12 C17 C16 -177.85(13)
