#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/79/2227976.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227976
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-2-(4-chlorophenyl)-3-ethylsulfinyl-7-methyl-1-benzofuran
;
_journal_coeditor_code           RZ2506
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2960
_journal_paper_doi               10.1107/S1600536810042790
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H14 Br Cl O2 S'
_chemical_formula_moiety         'C17 H14 Br Cl O2 S'
_chemical_formula_sum            'C17 H14 Br Cl O2 S'
_chemical_formula_weight         397.70
_chemical_name_systematic
;
5-Bromo-2-(4-chlorophenyl)-3-ethylsulfinyl-7-methyl-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
_cell_angle_alpha                68.6900(10)
_cell_angle_beta                 89.2230(10)
_cell_angle_gamma                70.9410(10)
_cell_formula_units_Z            2
_cell_length_a                   7.31590(10)
_cell_length_b                   10.3502(2)
_cell_length_c                   11.8936(2)
_cell_measurement_reflns_used    8401
_cell_measurement_temperature    179(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.25
_cell_volume                     787.36(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) 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      179(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'
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14107
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.916
_exptl_absorpt_correction_T_max  0.5235
_exptl_absorpt_correction_T_min  0.4852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0246
_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)+(0.0362P)²+0.2277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0664
_reflns_number_gt                3342
_reflns_number_total             3657
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2506.cif
_cod_data_source_block           I
_cod_database_code               2227976
_cod_database_fobs_code          2227976
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_disorder_assembly
_atom_site_disorder_group
Br Br 0.99643(3) 0.279456(19) 1.076951(15) 0.03226(7) Uani d . 1 . .
Cl Cl 0.44218(8) 0.83326(6) -0.02326(4) 0.04120(13) Uani d . 1 . .
S S 0.64454(6) 0.80596(4) 0.58771(4) 0.02307(10) Uani d . 1 . .
O O1 0.80545(16) 0.41969(12) 0.55116(10) 0.0217(2) Uani d . 1 . .
O O2 0.8019(2) 0.81168(15) 0.66239(13) 0.0357(3) Uani d . 1 . .
C C1 0.7086(2) 0.62059(16) 0.60048(14) 0.0203(3) Uani d . 1 . .
C C2 0.7957(2) 0.49198(17) 0.71094(15) 0.0207(3) Uani d . 1 . .
C C3 0.8333(2) 0.46726(18) 0.83324(15) 0.0232(3) Uani d . 1 . .
H H3 0.7941 0.5455 0.8620 0.028 Uiso calc R 1 . .
C C4 0.9307(2) 0.32235(19) 0.91027(15) 0.0243(3) Uani d . 1 . .
C C5 0.9924(2) 0.20505(18) 0.87039(16) 0.0249(3) Uani d . 1 . .
H H5 1.0605 0.1081 0.9273 0.030 Uiso calc R 1 . .
C C6 0.9561(2) 0.22752(17) 0.74956(15) 0.0225(3) Uani d . 1 . .
C C7 0.8541(2) 0.37343(17) 0.67424(14) 0.0202(3) Uani d . 1 . .
C C8 0.7168(2) 0.57118(16) 0.50771(15) 0.0206(3) Uani d . 1 . .
C C9 1.0223(3) 0.10666(18) 0.70187(17) 0.0289(4) Uani d . 1 . .
H H9A 1.1085 0.0162 0.7657 0.043 Uiso calc R 1 . .
H H9B 1.0930 0.1359 0.6318 0.043 Uiso calc R 1 . .
H H9C 0.9089 0.0886 0.6769 0.043 Uiso calc R 1 . .
C C10 0.6517(2) 0.63921(17) 0.37745(15) 0.0211(3) Uani d . 1 . .
C C11 0.5182(2) 0.78327(18) 0.32282(16) 0.0253(3) Uani d . 1 . .
H H11 0.4701 0.8401 0.3710 0.030 Uiso calc R 1 . .
C C12 0.4555(2) 0.84388(19) 0.19966(16) 0.0280(4) Uani d . 1 . .
H H12 0.3666 0.9422 0.1628 0.034 Uiso calc R 1 . .
C C13 0.5241(3) 0.7592(2) 0.13105(15) 0.0277(4) Uani d . 1 . .
C C14 0.6558(3) 0.6165(2) 0.18176(16) 0.0282(4) Uani d . 1 . .
H H14 0.7013 0.5602 0.1329 0.034 Uiso calc R 1 . .
C C15 0.7202(2) 0.55713(18) 0.30474(15) 0.0251(3) Uani d . 1 . .
H H15 0.8118 0.4596 0.3403 0.030 Uiso calc R 1 . .
C C16 0.4362(3) 0.81428(19) 0.67208(17) 0.0283(4) Uani d . 1 . .
H H16A 0.4677 0.7232 0.7463 0.034 Uiso calc R 1 . .
H H16B 0.4054 0.8995 0.6974 0.034 Uiso calc R 1 . .
C C17 0.2605(3) 0.8300(2) 0.59514(19) 0.0319(4) Uani d . 1 . .
H H17A 0.2222 0.9245 0.5255 0.048 Uiso calc R 1 . .
H H17B 0.1522 0.8268 0.6442 0.048 Uiso calc R 1 . .
H H17C 0.2936 0.7489 0.5660 0.048 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'
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'
Cl Cl 0.1484 0.1585 '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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 Br O2 . 2_767 167.44(6) ?
O2 S C1 . . 106.73(7) ?
O2 S C16 . . 107.42(9) ?
C1 S C16 . . 98.10(8) ?
C7 O1 C8 . . 106.72(12) ?
C8 C1 C2 . . 107.07(14) ?
C8 C1 S . . 127.14(12) ?
C2 C1 S . . 124.97(12) ?
C7 C2 C3 . . 119.41(14) ?
C7 C2 C1 . . 105.01(14) ?
C3 C2 C1 . . 135.55(15) ?
C4 C3 C2 . . 116.31(15) ?
C4 C3 H3 . . 121.8 ?
C2 C3 H3 . . 121.8 ?
C3 C4 C5 . . 123.16(16) ?
C3 C4 Br . . 119.20(13) ?
C5 C4 Br . . 117.57(12) ?
C6 C5 C4 . . 121.28(15) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 114.60(15) ?
C5 C6 C9 . . 123.38(14) ?
C7 C6 C9 . . 122.01(15) ?
O1 C7 C2 . . 110.87(13) ?
O1 C7 C6 . . 123.88(14) ?
C2 C7 C6 . . 125.19(15) ?
C1 C8 O1 . . 110.31(13) ?
C1 C8 C10 . . 135.56(14) ?
O1 C8 C10 . . 114.12(13) ?
C6 C9 H9A . . 109.5 ?
C6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C15 . . 118.61(15) ?
C11 C10 C8 . . 122.03(15) ?
C15 C10 C8 . . 119.34(14) ?
C12 C11 C10 . . 120.86(16) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C13 C12 C11 . . 118.98(16) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C12 C13 C14 . . 121.83(16) ?
C12 C13 Cl . . 119.27(14) ?
C14 C13 Cl . . 118.90(15) ?
C13 C14 C15 . . 118.96(17) ?
C13 C14 H14 . . 120.5 ?
C15 C14 H14 . . 120.5 ?
C14 C15 C10 . . 120.75(16) ?
C14 C15 H15 . . 119.6 ?
C10 C15 H15 . . 119.6 ?
C17 C16 S . . 110.69(13) ?
C17 C16 H16A . . 109.5 ?
S C16 H16A . . 109.5 ?
C17 C16 H16B . . 109.5 ?
S C16 H16B . . 109.5 ?
H16A C16 H16B . . 108.1 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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 C4 . 1.8987(17) ?
Br O2 2_767 3.1254(14) ?
Cl C13 . 1.7385(17) ?
S O2 . 1.4925(13) ?
S C1 . 1.7683(16) ?
S C16 . 1.8092(18) ?
O1 C7 . 1.3756(19) ?
O1 C8 . 1.3792(18) ?
C1 C8 . 1.368(2) ?
C1 C2 . 1.450(2) ?
C2 C7 . 1.386(2) ?
C2 C3 . 1.397(2) ?
C3 C4 . 1.385(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.399(2) ?
C5 C6 . 1.385(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.392(2) ?
C6 C9 . 1.495(2) ?
C8 C10 . 1.460(2) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.400(2) ?
C10 C15 . 1.402(2) ?
C11 C12 . 1.383(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.381(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.383(3) ?
C14 C15 . 1.384(2) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 C17 . 1.518(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 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
C17 H17B O2 1_455 0.98 2.62 3.488(2) 147.8
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S C1 C8 . . . . -129.10(15) ?
C16 S C1 C8 . . . . 119.89(15) ?
O2 S C1 C2 . . . . 39.12(15) ?
C16 S C1 C2 . . . . -71.89(15) ?
C8 C1 C2 C7 . . . . 1.23(17) ?
S C1 C2 C7 . . . . -168.97(12) ?
C8 C1 C2 C3 . . . . 179.21(17) ?
S C1 C2 C3 . . . . 9.0(3) ?
C7 C2 C3 C4 . . . . 0.8(2) ?
C1 C2 C3 C4 . . . . -176.99(17) ?
C2 C3 C4 C5 . . . . 0.8(2) ?
C2 C3 C4 Br . . . . 177.69(11) ?
O2 Br C4 C3 2_767 . . . -115.1(3) ?
O2 Br C4 C5 2_767 . . . 62.0(3) ?
C3 C4 C5 C6 . . . . -1.0(3) ?
Br C4 C5 C6 . . . . -177.90(12) ?
C4 C5 C6 C7 . . . . -0.5(2) ?
C4 C5 C6 C9 . . . . 178.70(16) ?
C8 O1 C7 C2 . . . . 0.92(16) ?
C8 O1 C7 C6 . . . . -176.43(15) ?
C3 C2 C7 O1 . . . . -179.71(13) ?
C1 C2 C7 O1 . . . . -1.33(17) ?
C3 C2 C7 C6 . . . . -2.4(2) ?
C1 C2 C7 C6 . . . . 175.98(15) ?
C5 C6 C7 O1 . . . . 179.15(14) ?
C9 C6 C7 O1 . . . . 0.0(2) ?
C5 C6 C7 C2 . . . . 2.2(2) ?
C9 C6 C7 C2 . . . . -177.01(15) ?
C2 C1 C8 O1 . . . . -0.72(17) ?
S C1 C8 O1 . . . . 169.20(11) ?
C2 C1 C8 C10 . . . . 177.77(16) ?
S C1 C8 C10 . . . . -12.3(3) ?
C7 O1 C8 C1 . . . . -0.09(16) ?
C7 O1 C8 C10 . . . . -178.93(12) ?
C1 C8 C10 C11 . . . . -14.7(3) ?
O1 C8 C10 C11 . . . . 163.78(14) ?
C1 C8 C10 C15 . . . . 167.14(18) ?
O1 C8 C10 C15 . . . . -14.4(2) ?
C15 C10 C11 C12 . . . . -0.3(2) ?
C8 C10 C11 C12 . . . . -178.48(15) ?
C10 C11 C12 C13 . . . . 1.1(3) ?
C11 C12 C13 C14 . . . . -1.0(3) ?
C11 C12 C13 Cl . . . . 178.70(13) ?
C12 C13 C14 C15 . . . . 0.1(3) ?
Cl C13 C14 C15 . . . . -179.60(13) ?
C13 C14 C15 C10 . . . . 0.7(3) ?
C11 C10 C15 C14 . . . . -0.7(2) ?
C8 C10 C15 C14 . . . . 177.61(15) ?
O2 S C16 C17 . . . . 172.31(12) ?
C1 S C16 C17 . . . . -77.25(13) ?
