#------------------------------------------------------------------------------
#$Date: 2015-08-07 06:01:24 +0300 (Fri, 07 Aug 2015) $
#$Revision: 153028 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/09/2240971.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_2240971
loop_
_publ_author_name
'Choi, Hong Dae'
'Lee, Uk'
_publ_section_title
;
 Crystal structure of
 5-chloro-2-(2-fluorophenyl)-3-methylsulfinyl-1-benzofuran
;
_journal_coeditor_code           FY2120
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o621
_journal_page_last               o622
_journal_paper_doi               10.1107/S2056989015013948
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C15 H10 Cl F O2 S'
_chemical_formula_moiety         'C15 H10 Cl F O2 S'
_chemical_formula_sum            'C15 H10 Cl F O2 S'
_chemical_formula_weight         308.74
_chemical_name_systematic
;
5-Chloro-2-(2-fluorophenyl)-3-methylsulfinyl-1-benzofuran
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                92.7580(10)
_cell_angle_beta                 95.5090(10)
_cell_angle_gamma                112.3730(10)
_cell_formula_units_Z            2
_cell_length_a                   7.96260(10)
_cell_length_b                   8.35180(10)
_cell_length_c                   10.7127(2)
_cell_measurement_reflns_used    6796
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.41
_cell_measurement_theta_min      2.65
_cell_volume                     652.967(17)
_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
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12250
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.406
_diffrn_reflns_theta_min         1.918
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6901
_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_description       Block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.355
_exptl_crystal_size_min          0.318
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.260
_refine_ls_extinction_coef       0.042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0399P)²+0.2911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                3030
_reflns_number_total             3263
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fy2120sup1.cif
_cod_data_source_block           I
_cod_database_code               2240971
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_occupancy
Cl Cl1 0.80773(5) 0.60679(5) 0.52105(3) 0.03134(11) Uani d 1
S S1 0.20658(4) 0.19225(4) 0.10339(3) 0.02090(10) Uani d 1
F F1 0.22939(12) -0.06448(11) -0.07604(8) 0.0324(2) Uani d 1
O O1 0.70194(12) 0.36314(12) -0.00857(8) 0.02229(19) Uani d 1
O O2 0.18502(13) 0.32691(13) 0.18956(10) 0.0283(2) Uani d 1
C C1 0.44206(16) 0.27158(16) 0.08330(11) 0.0198(2) Uani d 1
C C2 0.58981(17) 0.37914(16) 0.17693(11) 0.0198(2) Uani d 1
C C3 0.60633(18) 0.43369(17) 0.30452(12) 0.0220(3) Uani d 1
H H3 0.5032 0.4009 0.3498 0.026 Uiso calc 1
C C4 0.77958(18) 0.53749(17) 0.36158(12) 0.0231(3) Uani d 1
C C5 0.93409(18) 0.58960(18) 0.29751(13) 0.0258(3) Uani d 1
H H5 1.0502 0.6620 0.3411 0.031 Uiso calc 1
C C6 0.91896(18) 0.53654(18) 0.17133(13) 0.0255(3) Uani d 1
H H6 1.0220 0.5701 0.1260 0.031 Uiso calc 1
C C7 0.74560(17) 0.43207(16) 0.11491(12) 0.0208(2) Uani d 1
C C8 0.51654(17) 0.26585(16) -0.02553(12) 0.0201(2) Uani d 1
C C9 0.44641(17) 0.17903(16) -0.15243(12) 0.0210(2) Uani d 1
C C10 0.30426(18) 0.01690(17) -0.17542(13) 0.0242(3) Uani d 1
C C11 0.2375(2) -0.06907(19) -0.29337(14) 0.0304(3) Uani d 1
H H11 0.1390 -0.1796 -0.3049 0.036 Uiso calc 1
C C12 0.3186(2) 0.0106(2) -0.39495(14) 0.0341(3) Uani d 1
H H12 0.2744 -0.0450 -0.4778 0.041 Uiso calc 1
C C13 0.4640(2) 0.1712(2) -0.37641(13) 0.0311(3) Uani d 1
H H13 0.5198 0.2238 -0.4466 0.037 Uiso calc 1
C C14 0.52834(19) 0.25528(17) -0.25675(12) 0.0244(3) Uani d 1
H H14 0.6282 0.3649 -0.2451 0.029 Uiso calc 1
C C15 0.2029(2) 0.02115(19) 0.20017(15) 0.0323(3) Uani d 1
H H15A 0.2950 0.0697 0.2741 0.048 Uiso calc 1
H H15B 0.2302 -0.0665 0.1516 0.048 Uiso calc 1
H H15C 0.0814 -0.0330 0.2276 0.048 Uiso calc 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 C1 105.84(6)
O2 S1 C15 105.10(7)
C1 S1 C15 97.80(6)
C7 O1 C8 106.59(9)
C8 C1 C2 106.80(11)
C8 C1 S1 127.53(10)
C2 C1 S1 125.04(9)
C7 C2 C3 119.16(11)
C7 C2 C1 105.31(11)
C3 C2 C1 135.52(12)
C4 C3 C2 116.81(12)
C4 C3 H3 121.6
C2 C3 H3 121.6
C3 C4 C5 123.12(12)
C3 C4 Cl1 118.55(10)
C5 C4 Cl1 118.33(10)
C6 C5 C4 120.45(12)
C6 C5 H5 119.8
C4 C5 H5 119.8
C7 C6 C5 116.19(12)
C7 C6 H6 121.9
C5 C6 H6 121.9
O1 C7 C6 125.31(11)
O1 C7 C2 110.42(11)
C6 C7 C2 124.26(12)
C1 C8 O1 110.87(11)
C1 C8 C9 135.10(12)
O1 C8 C9 114.01(10)
C10 C9 C14 117.07(12)
C10 C9 C8 122.54(12)
C14 C9 C8 120.32(12)
F1 C10 C11 117.65(12)
F1 C10 C9 118.49(12)
C11 C10 C9 123.83(13)
C10 C11 C12 117.90(14)
C10 C11 H11 121.1
C12 C11 H11 121.0
C11 C12 C13 120.39(13)
C11 C12 H12 119.8
C13 C12 H12 119.8
C14 C13 C12 120.60(13)
C14 C13 H13 119.7
C12 C13 H13 119.7
C13 C14 C9 120.18(13)
C13 C14 H14 119.9
C9 C14 H14 119.9
S1 C15 H15A 109.5
S1 C15 H15B 109.5
H15A C15 H15B 109.5
S1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.7425(13)
S1 O2 1.4913(10)
S1 C1 1.7739(12)
S1 C15 1.7983(14)
F1 C10 1.3542(15)
O1 C7 1.3741(15)
O1 C8 1.3762(15)
C1 C8 1.3647(17)
C1 C2 1.4420(17)
C2 C7 1.3945(17)
C2 C3 1.3976(17)
C3 C4 1.3802(18)
C3 H3 0.9500
C4 C5 1.3990(19)
C5 C6 1.3815(19)
C5 H5 0.9500
C6 C7 1.3800(18)
C6 H6 0.9500
C8 C9 1.4618(17)
C9 C10 1.3867(18)
C9 C14 1.4043(18)
C10 C11 1.3740(19)
C11 C12 1.386(2)
C11 H11 0.9500
C12 C13 1.388(2)
C12 H12 0.9500
C13 C14 1.3830(19)
C13 H13 0.9500
C14 H14 0.9500
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 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_765 0.95 2.53 3.4756(16) 175.5
C14 H14 O2 2_665 0.95 2.44 3.3591(17) 162.5
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 -138.17(12)
C15 S1 C1 C8 113.63(13)
O2 S1 C1 C2 31.48(12)
C15 S1 C1 C2 -76.71(12)
C8 C1 C2 C7 0.43(14)
S1 C1 C2 C7 -171.01(9)
C8 C1 C2 C3 -178.84(14)
S1 C1 C2 C3 9.7(2)
C7 C2 C3 C4 -0.38(18)
C1 C2 C3 C4 178.82(13)
C2 C3 C4 C5 0.61(19)
C2 C3 C4 Cl1 -179.26(9)
C3 C4 C5 C6 -0.5(2)
Cl1 C4 C5 C6 179.35(11)
C4 C5 C6 C7 0.2(2)
C8 O1 C7 C6 179.14(12)
C8 O1 C7 C2 0.19(14)
C5 C6 C7 O1 -178.76(12)
C5 C6 C7 C2 0.0(2)
C3 C2 C7 O1 179.03(11)
C1 C2 C7 O1 -0.39(14)
C3 C2 C7 C6 0.1(2)
C1 C2 C7 C6 -179.34(12)
C2 C1 C8 O1 -0.33(14)
S1 C1 C8 O1 170.83(9)
C2 C1 C8 C9 178.19(13)
S1 C1 C8 C9 -10.6(2)
C7 O1 C8 C1 0.10(14)
C7 O1 C8 C9 -178.76(10)
C1 C8 C9 C10 -33.0(2)
O1 C8 C9 C10 145.51(12)
C1 C8 C9 C14 150.06(15)
O1 C8 C9 C14 -31.45(17)
C14 C9 C10 F1 176.27(11)
C8 C9 C10 F1 -0.78(19)
C14 C9 C10 C11 -1.8(2)
C8 C9 C10 C11 -178.88(13)
F1 C10 C11 C12 -177.47(13)
C9 C10 C11 C12 0.6(2)
C10 C11 C12 C13 0.8(2)
C11 C12 C13 C14 -1.0(2)
C12 C13 C14 C9 -0.2(2)
C10 C9 C14 C13 1.59(19)
C8 C9 C14 C13 178.71(12)

_cod_database_fobs_code 2240971
