#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/53/2225305.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_2225305
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-(4-Fluorophenyl)-5,6-methylenedioxy-3-methylsulfinyl-1-benzofuran
;
_journal_coeditor_code           KJ2140
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o605
_journal_paper_doi               10.1107/S1600536810004745
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H11 F O4 S'
_chemical_formula_moiety         'C16 H11 F O4 S'
_chemical_formula_sum            'C16 H11 F O4 S'
_chemical_formula_weight         318.31
_chemical_name_systematic
;
2-(4-Fluorophenyl)-5,6-methylenedioxy-3-methylsulfinyl-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                85.7350(10)
_cell_angle_beta                 86.3190(10)
_cell_angle_gamma                68.1100(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0283(7)
_cell_length_b                   8.4072(7)
_cell_length_c                   10.6611(9)
_cell_measurement_reflns_used    4336
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.61
_cell_volume                     665.33(10)
_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      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  HELIOS
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4954
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.9476
_exptl_absorpt_correction_T_min  0.8990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.337
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/esd_max         <0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0477P)²+0.4337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                2153
_reflns_number_total             2325
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2140.cif
_cod_data_source_block           I
_cod_database_code               2225305
_cod_database_fobs_code          2225305
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
S S 0.80463(5) 0.18763(6) 0.60869(4) 0.02335(16) Uani d . 1 . .
F F 0.68941(16) -0.01363(16) 0.02490(11) 0.0385(3) Uani d . 1 . .
O O1 0.29585(16) 0.35961(16) 0.51174(11) 0.0228(3) Uani d . 1 . .
O O2 0.25335(17) 0.57506(17) 0.98364(12) 0.0292(3) Uani d . 1 . .
O O3 -0.01602(17) 0.65674(17) 0.88470(12) 0.0285(3) Uani d . 1 . .
O O4 0.84924(18) 0.30301(18) 0.68884(15) 0.0372(4) Uani d . 1 . .
C C1 0.5684(2) 0.2707(2) 0.59585(16) 0.0206(4) Uani d . 1 . .
C C2 0.4380(2) 0.3671(2) 0.68856(16) 0.0204(4) Uani d . 1 . .
C C3 0.4467(2) 0.4134(2) 0.81182(16) 0.0225(4) Uani d . 1 . .
H H3 0.5537 0.3792 0.8537 0.027 Uiso calc R 1 . .
C C4 0.2853(2) 0.5124(2) 0.86443(16) 0.0229(4) Uani d . 1 . .
C C5 0.0711(3) 0.6920(2) 0.98677(18) 0.0289(4) Uani d . 1 . .
H H5A 0.0661 0.8093 0.9776 0.035 Uiso calc R 1 . .
H H5B 0.0117 0.6769 1.0664 0.035 Uiso calc R 1 . .
C C6 0.1218(2) 0.5638(2) 0.80438(17) 0.0222(4) Uani d . 1 . .
C C7 0.1075(2) 0.5200(2) 0.68512(17) 0.0237(4) Uani d . 1 . .
H H7 -0.0006 0.5531 0.6449 0.028 Uiso calc R 1 . .
C C8 0.2736(2) 0.4202(2) 0.63084(16) 0.0209(4) Uani d . 1 . .
C C9 0.4775(2) 0.2695(2) 0.49235(16) 0.0214(4) Uani d . 1 . .
C C10 0.5313(2) 0.1926(2) 0.37027(16) 0.0214(4) Uani d . 1 . .
C C11 0.4330(2) 0.2717(2) 0.26424(16) 0.0227(4) Uani d . 1 . .
H H11 0.3323 0.3721 0.2719 0.027 Uiso calc R 1 . .
C C12 0.4845(2) 0.2015(2) 0.14773(17) 0.0251(4) Uani d . 1 . .
H H12 0.4192 0.2530 0.0769 0.030 Uiso calc R 1 . .
C C13 0.6347(2) 0.0537(2) 0.13962(17) 0.0259(4) Uani d . 1 . .
C C14 0.7337(2) -0.0306(2) 0.24219(17) 0.0272(4) Uani d . 1 . .
H H14 0.8334 -0.1315 0.2336 0.033 Uiso calc R 1 . .
C C15 0.6797(2) 0.0397(2) 0.35841(17) 0.0258(4) Uani d . 1 . .
H H15 0.7430 -0.0156 0.4292 0.031 Uiso calc R 1 . .
C C16 0.8251(3) -0.0009(3) 0.70708(19) 0.0321(4) Uani d . 1 . .
H H16A 0.9492 -0.0629 0.7248 0.048 Uiso calc R 1 . .
H H16B 0.7803 -0.0726 0.6646 0.048 Uiso calc R 1 . .
H H16C 0.7568 0.0320 0.7845 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'
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'
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
O4 S C1 . . 107.29(8) ?
O4 S C16 . . 105.76(9) ?
C1 S C16 . . 98.28(9) ?
C8 O1 C9 . . 106.48(13) ?
C4 O2 C5 . . 105.53(13) ?
C6 O3 C5 . . 105.04(14) ?
C9 C1 C2 . . 107.49(15) ?
C9 C1 S . . 126.25(13) ?
C2 C1 S . . 126.00(13) ?
C8 C2 C3 . . 120.39(16) ?
C8 C2 C1 . . 104.84(15) ?
C3 C2 C1 . . 134.76(16) ?
C4 C3 C2 . . 114.39(16) ?
C4 C3 H3 . . 122.8 ?
C2 C3 H3 . . 122.8 ?
C3 C4 O2 . . 126.99(16) ?
C3 C4 C6 . . 124.06(16) ?
O2 C4 C6 . . 108.93(15) ?
O2 C5 O3 . . 107.68(14) ?
O2 C5 H5A . . 110.2 ?
O3 C5 H5A . . 110.2 ?
O2 C5 H5B . . 110.2 ?
O3 C5 H5B . . 110.2 ?
H5A C5 H5B . . 108.5 ?
C7 C6 O3 . . 127.18(16) ?
C7 C6 C4 . . 123.29(16) ?
O3 C6 C4 . . 109.50(15) ?
C6 C7 C8 . . 112.52(16) ?
C6 C7 H7 . . 123.7 ?
C8 C7 H7 . . 123.7 ?
O1 C8 C2 . . 110.69(15) ?
O1 C8 C7 . . 123.97(15) ?
C2 C8 C7 . . 125.34(16) ?
C1 C9 O1 . . 110.48(15) ?
C1 C9 C10 . . 133.97(16) ?
O1 C9 C10 . . 115.53(14) ?
C15 C10 C11 . . 119.35(16) ?
C15 C10 C9 . . 120.68(16) ?
C11 C10 C9 . . 119.97(16) ?
C12 C11 C10 . . 120.44(16) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C13 C12 C11 . . 118.26(16) ?
C13 C12 H12 . . 120.9 ?
C11 C12 H12 . . 120.9 ?
F C13 C12 . . 118.70(16) ?
F C13 C14 . . 118.04(16) ?
C12 C13 C14 . . 123.25(17) ?
C13 C14 C15 . . 117.97(17) ?
C13 C14 H14 . . 121.0 ?
C15 C14 H14 . . 121.0 ?
C14 C15 C10 . . 120.68(17) ?
C14 C15 H15 . . 119.7 ?
C10 C15 H15 . . 119.7 ?
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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S O4 . 1.4903(14) ?
S C1 . 1.7707(17) ?
S C16 . 1.7944(19) ?
F C13 . 1.363(2) ?
O1 C8 . 1.380(2) ?
O1 C9 . 1.380(2) ?
O2 C4 . 1.384(2) ?
O2 C5 . 1.426(2) ?
O3 C6 . 1.379(2) ?
O3 C5 . 1.436(2) ?
C1 C9 . 1.364(2) ?
C1 C2 . 1.443(2) ?
C2 C8 . 1.395(2) ?
C2 C3 . 1.411(2) ?
C3 C4 . 1.363(3) ?
C3 H3 . 0.9300 ?
C4 C6 . 1.401(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.373(3) ?
C7 C8 . 1.398(2) ?
C7 H7 . 0.9300 ?
C9 C10 . 1.464(2) ?
C10 C15 . 1.397(3) ?
C10 C11 . 1.398(2) ?
C11 C12 . 1.387(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.380(3) ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
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
_geom_hbond_publ_flag
C3 H3 O2 2_667 0.93 2.54 3.383(2) 151.1 y
C14 H14 O4 2_756 0.93 2.57 3.368(2) 144.1 y
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
O4 S C1 C9 . . . . 144.09(16) ?
C16 S C1 C9 . . . . -106.47(17) ?
O4 S C1 C2 . . . . -29.26(18) ?
C16 S C1 C2 . . . . 80.17(17) ?
C9 C1 C2 C8 . . . . -0.86(19) ?
S C1 C2 C8 . . . . 173.53(13) ?
C9 C1 C2 C3 . . . . -179.99(19) ?
S C1 C2 C3 . . . . -5.6(3) ?
C8 C2 C3 C4 . . . . -0.8(2) ?
C1 C2 C3 C4 . . . . 178.23(18) ?
C2 C3 C4 O2 . . . . 179.41(16) ?
C2 C3 C4 C6 . . . . 1.0(3) ?
C5 O2 C4 C3 . . . . 171.11(18) ?
C5 O2 C4 C6 . . . . -10.26(19) ?
C4 O2 C5 O3 . . . . 17.49(19) ?
C6 O3 C5 O2 . . . . -18.03(19) ?
C5 O3 C6 C7 . . . . -170.31(18) ?
C5 O3 C6 C4 . . . . 11.72(19) ?
C3 C4 C6 C7 . . . . -0.4(3) ?
O2 C4 C6 C7 . . . . -179.07(16) ?
C3 C4 C6 O3 . . . . 177.68(16) ?
O2 C4 C6 O3 . . . . -1.0(2) ?
O3 C6 C7 C8 . . . . -178.09(16) ?
C4 C6 C7 C8 . . . . -0.4(3) ?
C9 O1 C8 C2 . . . . -1.19(19) ?
C9 O1 C8 C7 . . . . 179.28(16) ?
C3 C2 C8 O1 . . . . -179.45(15) ?
C1 C2 C8 O1 . . . . 1.26(19) ?
C3 C2 C8 C7 . . . . 0.1(3) ?
C1 C2 C8 C7 . . . . -179.22(17) ?
C6 C7 C8 O1 . . . . 179.98(16) ?
C6 C7 C8 C2 . . . . 0.5(3) ?
C2 C1 C9 O1 . . . . 0.2(2) ?
S C1 C9 O1 . . . . -174.20(12) ?
C2 C1 C9 C10 . . . . -178.74(18) ?
S C1 C9 C10 . . . . 6.9(3) ?
C8 O1 C9 C1 . . . . 0.61(19) ?
C8 O1 C9 C10 . . . . 179.74(14) ?
C1 C9 C10 C15 . . . . 30.2(3) ?
O1 C9 C10 C15 . . . . -148.66(16) ?
C1 C9 C10 C11 . . . . -150.3(2) ?
O1 C9 C10 C11 . . . . 30.9(2) ?
C15 C10 C11 C12 . . . . -1.5(3) ?
C9 C10 C11 C12 . . . . 178.93(16) ?
C10 C11 C12 C13 . . . . -0.5(3) ?
C11 C12 C13 F . . . . -178.17(16) ?
C11 C12 C13 C14 . . . . 1.8(3) ?
F C13 C14 C15 . . . . 178.87(17) ?
C12 C13 C14 C15 . . . . -1.1(3) ?
C13 C14 C15 C10 . . . . -1.0(3) ?
C11 C10 C15 C14 . . . . 2.3(3) ?
C9 C10 C15 C14 . . . . -178.20(17) ?
