#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/20/2212027.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_2212027
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Hee Kyung'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5,6-Methylenedioxy-3-methylsulfinyl-2-phenylbenzofuran
;
_journal_coeditor_code           BI2125
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o519
_journal_page_last               o520
_journal_paper_doi               10.1107/S1600536806055784
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H12 O4 S'
_chemical_formula_moiety         'C16 H12 O4 S'
_chemical_formula_sum            'C16 H12 O4 S'
_chemical_formula_weight         300.32
_chemical_name_systematic
;
5,6-Methylenedioxy-3-methylsulfinyl-2-phenyl-1-benzofuran
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.1960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4000(5)
_cell_length_b                   15.7770(10)
_cell_length_c                   11.3155(8)
_cell_measurement_reflns_used    4941
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.46
_cell_volume                     1295.94(15)
_computing_cell_refinement       SMART
_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      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7774
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.138
_refine_diff_density_min         -0.465
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0486
_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)+(0.0445P)²+1.6446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                2648
_reflns_number_total             2833
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2125.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2212027
_cod_database_fobs_code          2212027
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S S 0.51198(7) 0.05257(3) 0.79213(4) 0.02243(15) Uani d . 1
O O1 0.1269(3) -0.24499(10) 0.53721(15) 0.0340(4) Uani d . 1
O O2 0.0136(2) -0.19707(10) 0.34281(14) 0.0308(4) Uani d . 1
O O3 0.25918(19) 0.08537(9) 0.45181(12) 0.0197(3) Uani d . 1
O O4 0.6019(2) -0.03175(11) 0.81984(15) 0.0337(4) Uani d . 1
C C1 0.3846(3) 0.04853(13) 0.64262(17) 0.0189(4) Uani d . 1
C C2 0.2978(3) -0.02611(13) 0.58253(17) 0.0186(4) Uani d . 1
C C3 0.2742(3) -0.11107(13) 0.61696(18) 0.0224(4) Uani d . 1
H H3 0.3221 -0.1314 0.6938 0.027 Uiso calc R 1
C C4 0.1749(3) -0.16124(13) 0.52780(19) 0.0222(4) Uani d . 1
C C5 0.0429(3) -0.27114(14) 0.4178(2) 0.0275(5) Uani d . 1
H H5A -0.0736 -0.2990 0.4188 0.033 Uiso calc R 1
H H5B 0.1226 -0.3107 0.3868 0.033 Uiso calc R 1
C C6 0.1052(3) -0.13228(13) 0.41076(18) 0.0216(4) Uani d . 1
C C7 0.1263(3) -0.05049(13) 0.37412(18) 0.0214(4) Uani d . 1
H H7 0.0802 -0.0311 0.2965 0.026 Uiso calc R 1
C C8 0.2239(3) 0.00058(12) 0.46547(17) 0.0189(4) Uani d . 1
C C9 0.3573(3) 0.11363(13) 0.56109(17) 0.0185(4) Uani d . 1
C C10 0.4055(3) 0.20388(13) 0.56394(18) 0.0192(4) Uani d . 1
C C11 0.3868(3) 0.24948(14) 0.45584(19) 0.0248(4) Uani d . 1
H H11 0.3446 0.2222 0.3828 0.030 Uiso calc R 1
C C12 0.4307(3) 0.33508(14) 0.4570(2) 0.0276(5) Uani d . 1
H H12 0.4150 0.3650 0.3850 0.033 Uiso calc R 1
C C13 0.4977(3) 0.37633(14) 0.5651(2) 0.0277(5) Uani d . 1
H H13 0.5305 0.4333 0.5654 0.033 Uiso calc R 1
C C14 0.5155(3) 0.33188(14) 0.6727(2) 0.0279(5) Uani d . 1
H H14 0.5597 0.3593 0.7453 0.034 Uiso calc R 1
C C15 0.4678(3) 0.24684(14) 0.67250(19) 0.0249(4) Uani d . 1
H H15 0.4773 0.2181 0.7452 0.030 Uiso calc R 1
C C16 0.3175(3) 0.05441(16) 0.8664(2) 0.0304(5) Uani d . 1
H H16A 0.3604 0.0568 0.9520 0.046 Uiso calc R 1
H H16B 0.2453 0.0041 0.8462 0.046 Uiso calc R 1
H H16C 0.2431 0.1033 0.8406 0.046 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O4 S C1 107.54(10)
O4 S C16 106.26(11)
C1 S C16 96.95(10)
C4 O1 C5 105.92(16)
C6 O2 C5 105.84(16)
C8 O3 C9 106.94(15)
C9 C1 C2 107.46(17)
C9 C1 S 126.75(16)
C2 C1 S 125.72(15)
C8 C2 C3 120.00(18)
C8 C2 C1 104.88(17)
C3 C2 C1 135.11(18)
C4 C3 C2 114.78(18)
C4 C3 H3 122.6
C2 C3 H3 122.6
C3 C4 O1 127.12(19)
C3 C4 C6 123.45(19)
O1 C4 C6 109.42(18)
O1 C5 O2 108.11(17)
O1 C5 H5A 110.1
O2 C5 H5A 110.1
O1 C5 H5B 110.1
O2 C5 H5B 110.1
H5A C5 H5B 108.4
C7 C6 O2 126.99(19)
C7 C6 C4 123.31(19)
O2 C6 C4 109.69(18)
C6 C7 C8 113.04(18)
C6 C7 H7 123.5
C8 C7 H7 123.5
O3 C8 C2 110.58(17)
O3 C8 C7 124.02(17)
C2 C8 C7 125.40(19)
C1 C9 O3 110.14(17)
C1 C9 C10 135.24(18)
O3 C9 C10 114.62(16)
C15 C10 C11 118.48(19)
C15 C10 C9 121.76(18)
C11 C10 C9 119.75(18)
C12 C11 C10 120.5(2)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 120.5(2)
C11 C12 H12 119.8
C13 C12 H12 119.8
C14 C13 C12 119.5(2)
C14 C13 H13 120.3
C12 C13 H13 120.3
C15 C14 C13 120.4(2)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C10 120.6(2)
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_distance
S O4 1.4930(17)
S C1 1.771(2)
S C16 1.802(2)
O1 C4 1.378(3)
O1 C5 1.434(3)
O2 C6 1.376(2)
O2 C5 1.436(3)
O3 C8 1.377(2)
O3 C9 1.381(2)
C1 C9 1.369(3)
C1 C2 1.446(3)
C2 C8 1.396(3)
C2 C3 1.416(3)
C3 C4 1.377(3)
C3 H3 0.930
C4 C6 1.401(3)
C5 H5A 0.970
C5 H5B 0.970
C6 C7 1.373(3)
C7 C8 1.396(3)
C7 H7 0.930
C9 C10 1.467(3)
C10 C15 1.400(3)
C10 C11 1.403(3)
C11 C12 1.389(3)
C11 H11 0.930
C12 C13 1.389(3)
C12 H12 0.930
C13 C14 1.389(3)
C13 H13 0.930
C14 C15 1.387(3)
C14 H14 0.930
C15 H15 0.930
C16 H16A 0.960
C16 H16B 0.960
C16 H16C 0.960
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
O4 S C1 C9 -145.68(18)
C16 S C1 C9 104.8(2)
O4 S C1 C2 31.0(2)
C16 S C1 C2 -78.54(19)
C9 C1 C2 C8 0.5(2)
S C1 C2 C8 -176.75(15)
C9 C1 C2 C3 -178.5(2)
S C1 C2 C3 4.3(3)
C8 C2 C3 C4 -0.5(3)
C1 C2 C3 C4 178.3(2)
C2 C3 C4 O1 -178.0(2)
C2 C3 C4 C6 1.4(3)
C5 O1 C4 C3 -173.8(2)
C5 O1 C4 C6 6.7(2)
C4 O1 C5 O2 -10.1(2)
C6 O2 C5 O1 9.6(2)
C5 O2 C6 C7 175.4(2)
C5 O2 C6 C4 -5.5(2)
C3 C4 C6 C7 -1.2(3)
O1 C4 C6 C7 178.30(19)
C3 C4 C6 O2 179.69(19)
O1 C4 C6 O2 -0.8(2)
O2 C6 C7 C8 178.86(19)
C4 C6 C7 C8 -0.1(3)
C9 O3 C8 C2 0.2(2)
C9 O3 C8 C7 179.71(18)
C3 C2 C8 O3 178.75(17)
C1 C2 C8 O3 -0.4(2)
C3 C2 C8 C7 -0.8(3)
C1 C2 C8 C7 -179.92(19)
C6 C7 C8 O3 -178.43(18)
C6 C7 C8 C2 1.0(3)
C2 C1 C9 O3 -0.4(2)
S C1 C9 O3 176.79(14)
C2 C1 C9 C10 178.8(2)
S C1 C9 C10 -4.0(3)
C8 O3 C9 C1 0.1(2)
C8 O3 C9 C10 -179.25(16)
C1 C9 C10 C15 -13.5(4)
O3 C9 C10 C15 165.68(18)
C1 C9 C10 C11 167.5(2)
O3 C9 C10 C11 -13.4(3)
C15 C10 C11 C12 0.5(3)
C9 C10 C11 C12 179.58(19)
C10 C11 C12 C13 1.5(3)
C11 C12 C13 C14 -1.9(3)
C12 C13 C14 C15 0.4(3)
C13 C14 C15 C10 1.6(3)
C11 C10 C15 C14 -2.1(3)
C9 C10 C15 C14 178.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125556
