#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/07/2210762.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_2210762
loop_
_publ_author_name
'Choi, Hong Dae'
'Woo, Hyun Mi'
'Seo,  Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-(4-Bromophenyl)-2-methyl-3-methylsulfanyl-1-benzofuran
;
_journal_coeditor_code           RZ2062
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4253
_journal_page_last               o4254
_journal_paper_doi               10.1107/S1600536806034441
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H13 Br O S'
_chemical_formula_moiety         'C16 H13 Br O S'
_chemical_formula_sum            'C16 H13 Br O S'
_chemical_formula_weight         333.23
_chemical_name_systematic
;
5-(4-Bromophenyl)-2-methyl-3-methylsulfanyl-1-benzofuran
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.4410(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4244(8)
_cell_length_b                   7.8195(5)
_cell_length_c                   15.9340(10)
_cell_measurement_reflns_used    4422
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.39
_cell_volume                     1404.15(16)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8283
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    3.064
_exptl_absorpt_correction_T_max  0.3480
_exptl_absorpt_correction_T_min  0.1930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.618
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0414P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                2559
_reflns_number_total             3058
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2062.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210762
_cod_database_fobs_code          2210762
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br Br 0.461557(19) 0.47770(3) 0.243584(13) 0.03749(9) Uani d . 1
S S 1.22121(5) 0.99648(6) 0.53221(3) 0.02846(13) Uani d . 1
O O 1.36259(11) 0.58506(17) 0.44406(8) 0.0288(3) Uani d . 1
C C1 0.62777(19) 0.5022(2) 0.27806(13) 0.0273(4) Uani d . 1
C C2 0.70376(19) 0.4566(3) 0.22250(12) 0.0325(4) Uani d . 1
H H2 0.6736 0.4154 0.1685 0.039 Uiso calc R 1
C C3 0.82478(19) 0.4728(2) 0.24795(12) 0.0302(4) Uani d . 1
H H3 0.8756 0.4422 0.2105 0.036 Uiso calc R 1
C C4 0.87289(18) 0.5344(2) 0.32907(11) 0.0254(4) Uani d . 1
C C5 0.79343(17) 0.5808(2) 0.38319(11) 0.0256(4) Uani d . 1
H H5 0.8230 0.6224 0.4372 0.031 Uiso calc R 1
C C6 0.67168(17) 0.5662(2) 0.35837(11) 0.0275(4) Uani d . 1
H H6 0.6202 0.5989 0.3950 0.033 Uiso calc R 1
C C7 1.00273(17) 0.5456(2) 0.35767(11) 0.0255(4) Uani d . 1
C C8 1.07890(18) 0.4173(2) 0.33403(11) 0.0294(4) Uani d . 1
H H8 1.0457 0.3277 0.2998 0.035 Uiso calc R 1
C C9 1.19997(18) 0.4203(3) 0.35975(12) 0.0303(4) Uani d . 1
H H9 1.2489 0.3352 0.3440 0.036 Uiso calc R 1
C C10 1.24519(17) 0.5574(2) 0.41061(11) 0.0263(4) Uani d . 1
C C11 1.36592(16) 0.7351(2) 0.49087(11) 0.0259(4) Uani d . 1
C C12 1.25550(16) 0.8018(2) 0.48722(11) 0.0242(4) Uani d . 1
C C13 1.17421(16) 0.6863(2) 0.43554(10) 0.0234(4) Uani d . 1
C C14 1.05175(16) 0.6801(2) 0.40936(11) 0.0250(4) Uani d . 1
H H14 1.0032 0.7647 0.4261 0.030 Uiso calc R 1
C C15 1.48489(16) 0.7870(3) 0.53517(13) 0.0328(5) Uani d . 1
H H15A 1.4779 0.8885 0.5678 0.049 Uiso calc R 1
H H15B 1.5356 0.8093 0.4940 0.049 Uiso calc R 1
H H15C 1.5183 0.6966 0.5724 0.049 Uiso calc R 1
C C16 1.1608(2) 0.9218(3) 0.62393(13) 0.0409(5) Uani d . 1
H H16A 1.0867 0.8648 0.6053 0.061 Uiso calc R 1
H H16B 1.1482 1.0176 0.6591 0.061 Uiso calc R 1
H H16C 1.2156 0.8436 0.6560 0.061 Uiso calc R 1
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'
S S 0.1246 0.1234 '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'
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
_geom_angle_publ_flag
C12 S C16 100.96(9) yes
C10 O C11 106.26(14) yes
C2 C1 C6 120.82(19) ?
C2 C1 Br 119.44(15) yes
C6 C1 Br 119.74(15) yes
C3 C2 C1 119.40(18) ?
C3 C2 H2 120.3 ?
C1 C2 H2 120.3 ?
C2 C3 C4 121.57(19) ?
C2 C3 H3 119.2 ?
C4 C3 H3 119.2 ?
C5 C4 C3 117.44(18) ?
C5 C4 C7 120.91(16) ?
C3 C4 C7 121.63(17) ?
C6 C5 C4 121.67(16) ?
C6 C5 H5 119.2 ?
C4 C5 H5 119.2 ?
C5 C6 C1 119.08(17) ?
C5 C6 H6 120.5 ?
C1 C6 H6 120.5 ?
C14 C7 C8 119.04(18) ?
C14 C7 C4 120.72(17) ?
C8 C7 C4 120.23(17) ?
C9 C8 C7 122.62(17) ?
C9 C8 H8 118.7 ?
C7 C8 H8 118.7 ?
C8 C9 C10 116.44(17) ?
C8 C9 H9 121.8 ?
C10 C9 H9 121.8 ?
O C10 C9 126.26(17) ?
O C10 C13 110.62(16) ?
C9 C10 C13 123.12(18) ?
C12 C11 O 111.00(16) ?
C12 C11 C15 133.53(17) ?
O C11 C15 115.45(15) ?
C11 C12 C13 106.82(16) ?
C11 C12 S 125.74(14) ?
C13 C12 S 127.36(14) ?
C10 C13 C14 119.51(17) ?
C10 C13 C12 105.30(16) ?
C14 C13 C12 135.19(17) ?
C13 C14 C7 119.27(17) ?
C13 C14 H14 120.4 ?
C7 C14 H14 120.4 ?
C11 C15 H15A 109.5 ?
C11 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C11 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
S C16 H16A 109.5 ?
S C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
S C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C1 1.898(2) yes
S C12 1.7543(18) yes
S C16 1.812(2) yes
O C10 1.377(2) yes
O C11 1.387(2) yes
C1 C2 1.385(3) ?
C1 C6 1.389(3) ?
C2 C3 1.381(3) ?
C2 H2 0.9300 ?
C3 C4 1.404(3) ?
C3 H3 0.9300 ?
C4 C5 1.398(3) ?
C4 C7 1.481(3) ?
C5 C6 1.387(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C14 1.395(2) ?
C7 C8 1.419(3) ?
C8 C9 1.377(3) ?
C8 H8 0.9300 ?
C9 C10 1.391(3) ?
C9 H9 0.9300 ?
C10 C13 1.392(2) ?
C11 C12 1.357(2) ?
C11 C15 1.482(2) ?
C12 C13 1.451(2) ?
C13 C14 1.394(2) ?
C14 H14 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
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
C2 H2 Cg 2_745 0.93 2.83 3.604(3) 141.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127136
