#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/28/2222816.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_2222816
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Iodo-2-phenyl-3-phenylsulfinyl-1-benzofuran
;
_journal_coeditor_code           NG2605
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1809
_journal_paper_doi               10.1107/S1600536809024556
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H13 I O2 S'
_chemical_formula_moiety         'C20 H13 I O2 S'
_chemical_formula_sum            'C20 H13 I O2 S'
_chemical_formula_weight         444.26
_chemical_name_systematic
;
5-Iodo-2-phenyl-3-phenylsulfinyl-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                113.3810(10)
_cell_angle_beta                 92.6400(10)
_cell_angle_gamma                98.0470(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3544(4)
_cell_length_b                   9.7565(5)
_cell_length_c                   10.2808(5)
_cell_measurement_reflns_used    6672
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.17
_cell_volume                     847.42(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_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      273(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7217
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.021
_exptl_absorpt_correction_T_max  0.665
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.656
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0181
_refine_ls_R_factor_gt           0.0173
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0224P)²+0.4472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0440
_refine_ls_wR_factor_ref         0.0444
_reflns_number_gt                3503
_reflns_number_total             3616
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2605.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2222816
_cod_database_fobs_code          2222816
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
I I 0.041308(11) 0.682844(11) 0.391884(12) 0.02610(5) Uani d . 1 . .
S S 0.15151(4) 0.00846(5) 0.27065(4) 0.02113(8) Uani d . 1 . .
O O1 0.23863(13) 0.11727(14) -0.05193(12) 0.0244(2) Uani d . 1 . .
O O2 0.01344(13) 0.05325(15) 0.32919(13) 0.0278(3) Uani d . 1 . .
C C1 0.19488(18) 0.09925(19) 0.15550(17) 0.0213(3) Uani d . 1 . .
C C2 0.16806(17) 0.24593(19) 0.16717(17) 0.0212(3) Uani d . 1 . .
C C3 0.12402(18) 0.37088(19) 0.27157(18) 0.0229(3) Uani d . 1 . .
H H3 0.1038 0.3714 0.3595 0.027 Uiso calc R 1 . .
C C4 0.11164(18) 0.49421(19) 0.23915(18) 0.0231(3) Uani d . 1 . .
C C5 0.14158(19) 0.4962(2) 0.10730(19) 0.0263(3) Uani d . 1 . .
H H5 0.1329 0.5815 0.0901 0.032 Uiso calc R 1 . .
C C6 0.1841(2) 0.3719(2) 0.00232(19) 0.0274(4) Uani d . 1 . .
H H6 0.2037 0.3707 -0.0860 0.033 Uiso calc R 1 . .
C C7 0.19590(18) 0.24964(19) 0.03641(18) 0.0231(3) Uani d . 1 . .
C C8 0.23701(18) 0.02755(19) 0.02314(17) 0.0222(3) Uani d . 1 . .
C C9 0.28197(18) -0.11933(19) -0.05014(18) 0.0223(3) Uani d . 1 . .
C C10 0.23677(19) -0.2044(2) -0.19558(19) 0.0265(3) Uani d . 1 . .
H H10 0.1800 -0.1671 -0.2463 0.032 Uiso calc R 1 . .
C C11 0.2777(2) -0.3454(2) -0.2632(2) 0.0315(4) Uani d . 1 . .
H H11 0.2461 -0.4036 -0.3592 0.038 Uiso calc R 1 . .
C C12 0.3653(2) -0.4000(2) -0.1890(2) 0.0347(4) Uani d . 1 . .
H H12 0.3929 -0.4939 -0.2355 0.042 Uiso calc R 1 . .
C C13 0.4117(2) -0.3148(2) -0.0455(2) 0.0344(4) Uani d . 1 . .
H H13 0.4706 -0.3515 0.0041 0.041 Uiso calc R 1 . .
C C14 0.3700(2) -0.1747(2) 0.0242(2) 0.0286(4) Uani d . 1 . .
H H14 0.4009 -0.1178 0.1206 0.034 Uiso calc R 1 . .
C C15 0.29386(18) 0.10909(19) 0.41498(17) 0.0216(3) Uani d . 1 . .
C C16 0.4258(2) 0.1827(2) 0.3995(2) 0.0333(4) Uani d . 1 . .
H H16 0.4411 0.1914 0.3142 0.040 Uiso calc R 1 . .
C C17 0.5347(2) 0.2429(3) 0.5131(2) 0.0412(5) Uani d . 1 . .
H H17 0.6233 0.2931 0.5041 0.049 Uiso calc R 1 . .
C C18 0.5124(2) 0.2288(2) 0.6400(2) 0.0342(4) Uani d . 1 . .
H H18 0.5864 0.2684 0.7152 0.041 Uiso calc R 1 . .
C C19 0.3803(2) 0.1560(2) 0.65465(19) 0.0287(4) Uani d . 1 . .
H H19 0.3655 0.1473 0.7400 0.034 Uiso calc R 1 . .
C C20 0.26963(19) 0.09587(19) 0.54241(18) 0.0244(3) Uani d . 1 . .
H H20 0.1805 0.0474 0.5523 0.029 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'
I I -0.4742 1.8119 '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 I O2 . 2_566 165.84(5) ?
O2 S C1 . . 107.63(7) ?
O2 S C15 . . 106.00(8) ?
C1 S C15 . . 100.57(8) ?
C8 O1 C7 . . 106.38(12) ?
C8 C1 C2 . . 107.02(14) ?
C8 C1 S . . 123.64(13) ?
C2 C1 S . . 128.38(12) ?
C7 C2 C3 . . 119.26(15) ?
C7 C2 C1 . . 104.91(14) ?
C3 C2 C1 . . 135.83(15) ?
C4 C3 C2 . . 117.47(15) ?
C4 C3 H3 . . 121.3 ?
C2 C3 H3 . . 121.3 ?
C3 C4 C5 . . 122.37(16) ?
C3 C4 I . . 118.65(12) ?
C5 C4 I . . 118.96(12) ?
C6 C5 C4 . . 120.55(15) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C7 C6 C5 . . 116.34(16) ?
C7 C6 H6 . . 121.8 ?
C5 C6 H6 . . 121.8 ?
O1 C7 C6 . . 125.17(15) ?
O1 C7 C2 . . 110.82(14) ?
C6 C7 C2 . . 124.00(16) ?
C1 C8 O1 . . 110.87(14) ?
C1 C8 C9 . . 133.30(15) ?
O1 C8 C9 . . 115.81(14) ?
C14 C9 C10 . . 119.94(16) ?
C14 C9 C8 . . 120.26(15) ?
C10 C9 C8 . . 119.80(15) ?
C11 C10 C9 . . 119.19(17) ?
C11 C10 H10 . . 120.4 ?
C9 C10 H10 . . 120.4 ?
C12 C11 C10 . . 120.66(17) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.13(17) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 119.94(18) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C13 C14 C9 . . 120.11(17) ?
C13 C14 H14 . . 119.9 ?
C9 C14 H14 . . 119.9 ?
C16 C15 C20 . . 120.95(16) ?
C16 C15 S . . 123.40(13) ?
C20 C15 S . . 115.34(13) ?
C17 C16 C15 . . 119.05(17) ?
C17 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C18 C17 C16 . . 120.50(18) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C19 C18 C17 . . 120.03(18) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C19 C20 . . 120.30(16) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C19 C20 C15 . . 119.15(16) ?
C19 C20 H20 . . 120.4 ?
C15 C20 H20 . . 120.4 ?
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
I C4 . 2.104(2) ?
I O2 2_566 3.1240(10) ?
S O2 . 1.4970(10) ?
S C1 . 1.768(2) ?
S C15 . 1.799(2) ?
O1 C8 . 1.377(2) ?
O1 C7 . 1.378(2) ?
C1 C8 . 1.367(2) ?
C1 C2 . 1.447(2) ?
C2 C7 . 1.394(2) ?
C2 C3 . 1.397(2) ?
C3 C4 . 1.388(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.404(2) ?
C5 C6 . 1.389(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.387(2) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.463(2) ?
C9 C14 . 1.397(2) ?
C9 C10 . 1.401(2) ?
C10 C11 . 1.391(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.387(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.386(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.389(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.388(2) ?
C15 C20 . 1.392(2) ?
C16 C17 . 1.387(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.386(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.382(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.389(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
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
C10 H10 O2 2 0.93 2.53 3.438(2) 164.8
C19 H19 O1 1_556 0.93 2.59 3.483(2) 161.6
C20 H20 O2 2_556 0.93 2.53 3.412(2) 158.6
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 . . . . -134.10(15) ?
C15 S C1 C8 . . . . 115.21(15) ?
O2 S C1 C2 . . . . 33.18(17) ?
C15 S C1 C2 . . . . -77.52(16) ?
C8 C1 C2 C7 . . . . 0.54(18) ?
S C1 C2 C7 . . . . -168.40(13) ?
C8 C1 C2 C3 . . . . -179.78(19) ?
S C1 C2 C3 . . . . 11.3(3) ?
C7 C2 C3 C4 . . . . -0.6(2) ?
C1 C2 C3 C4 . . . . 179.73(18) ?
C2 C3 C4 C5 . . . . 0.0(2) ?
C2 C3 C4 I . . . . 178.71(12) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
I C4 C5 C6 . . . . -178.10(13) ?
C4 C5 C6 C7 . . . . -0.5(3) ?
C8 O1 C7 C6 . . . . 179.37(17) ?
C8 O1 C7 C2 . . . . 0.42(18) ?
C5 C6 C7 O1 . . . . -178.91(16) ?
C5 C6 C7 C2 . . . . -0.1(3) ?
C3 C2 C7 O1 . . . . 179.66(14) ?
C1 C2 C7 O1 . . . . -0.59(18) ?
C3 C2 C7 C6 . . . . 0.7(3) ?
C1 C2 C7 C6 . . . . -179.56(16) ?
C2 C1 C8 O1 . . . . -0.30(19) ?
S C1 C8 O1 . . . . 169.29(11) ?
C2 C1 C8 C9 . . . . 178.21(17) ?
S C1 C8 C9 . . . . -12.2(3) ?
C7 O1 C8 C1 . . . . -0.06(18) ?
C7 O1 C8 C9 . . . . -178.86(14) ?
C1 C8 C9 C14 . . . . -39.3(3) ?
O1 C8 C9 C14 . . . . 139.16(16) ?
C1 C8 C9 C10 . . . . 140.9(2) ?
O1 C8 C9 C10 . . . . -40.7(2) ?
C14 C9 C10 C11 . . . . 1.5(3) ?
C8 C9 C10 C11 . . . . -178.63(16) ?
C9 C10 C11 C12 . . . . -1.6(3) ?
C10 C11 C12 C13 . . . . 0.7(3) ?
C11 C12 C13 C14 . . . . 0.2(3) ?
C12 C13 C14 C9 . . . . -0.2(3) ?
C10 C9 C14 C13 . . . . -0.7(3) ?
C8 C9 C14 C13 . . . . 179.52(17) ?
O2 S C15 C16 . . . . -135.76(16) ?
C1 S C15 C16 . . . . -23.80(17) ?
O2 S C15 C20 . . . . 50.62(14) ?
C1 S C15 C20 . . . . 162.58(13) ?
C20 C15 C16 C17 . . . . 0.3(3) ?
S C15 C16 C17 . . . . -172.99(17) ?
C15 C16 C17 C18 . . . . 0.5(3) ?
C16 C17 C18 C19 . . . . -0.8(4) ?
C17 C18 C19 C20 . . . . 0.4(3) ?
C18 C19 C20 C15 . . . . 0.4(3) ?
C16 C15 C20 C19 . . . . -0.7(3) ?
S C15 C20 C19 . . . . 173.06(13) ?
