#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/85/2218588.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_2218588
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-(4-Iodophenyl)-5,7-dimethyl-3-methylsulfinyl-1-benzofuran
;
_journal_coeditor_code           ZL2115
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1088
_journal_paper_doi               10.1107/S1600536808014104
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C17 H15 I O2 S'
_chemical_formula_moiety         'C17 H15 I O2 S'
_chemical_formula_sum            'C17 H15 I O2 S'
_chemical_formula_weight         410.25
_chemical_melting_point_gt       450
_chemical_melting_point_lt       451
_chemical_name_systematic
;
2-(4-Iodophenyl)-5,7-dimethyl-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form.cif (version 2.0)'
_cell_angle_alpha                94.580(2)
_cell_angle_beta                 100.949(2)
_cell_angle_gamma                113.725(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6320(9)
_cell_length_b                   8.9170(10)
_cell_length_c                   11.6380(10)
_cell_measurement_reflns_used    5631
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.53
_cell_volume                     792.90(14)
_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      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_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            6882
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.152
_exptl_absorpt_correction_T_max  0.647
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.664
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0251
_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)+(0.0374P)²+0.4132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                3214
_reflns_number_total             3408
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2115.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -p_1
_cod_database_code               2218588
_cod_database_fobs_code          2218588
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
I I 0.26443(2) 0.23987(2) -0.006964(16) 0.03233(9) Uani d . 1
S S 0.10120(10) 0.19886(8) 0.60394(7) 0.02931(16) Uani d . 1
O O1 0.3173(3) 0.6586(2) 0.54519(18) 0.0262(4) Uani d . 1
O O2 0.2055(3) 0.1813(3) 0.7150(2) 0.0374(5) Uani d . 1
C C1 0.1717(4) 0.4134(3) 0.6002(3) 0.0262(6) Uani d . 1
C C2 0.2089(4) 0.5443(3) 0.6979(3) 0.0259(5) Uani d . 1
C C3 0.1802(4) 0.5533(4) 0.8114(3) 0.0294(6) Uani d . 1
H H3 0.1197 0.4569 0.8393 0.035 Uiso calc R 1
C C4 0.2430(4) 0.7078(4) 0.8822(3) 0.0309(6) Uani d . 1
C C5 0.3335(4) 0.8521(4) 0.8378(3) 0.0307(6) Uani d . 1
H H5 0.3738 0.9548 0.8862 0.037 Uiso calc R 1
C C6 0.3655(4) 0.8489(4) 0.7256(3) 0.0282(6) Uani d . 1
C C7 0.2995(4) 0.6914(3) 0.6586(3) 0.0256(6) Uani d . 1
C C8 0.2386(4) 0.4876(3) 0.5117(3) 0.0256(5) Uani d . 1
C C9 0.2460(4) 0.4269(3) 0.3936(2) 0.0247(5) Uani d . 1
C C10 0.1189(4) 0.2744(4) 0.3281(3) 0.0286(6) Uani d . 1
H H10 0.0280 0.2098 0.3599 0.034 Uiso calc R 1
C C11 0.1279(4) 0.2191(4) 0.2158(3) 0.0292(6) Uani d . 1
H H11 0.0438 0.1169 0.1728 0.035 Uiso calc R 1
C C12 0.2623(4) 0.3162(4) 0.1674(3) 0.0268(6) Uani d . 1
C C13 0.3902(4) 0.4699(4) 0.2319(3) 0.0289(6) Uani d . 1
H H13 0.4803 0.5348 0.1997 0.035 Uiso calc R 1
C C14 0.3811(4) 0.5239(3) 0.3437(3) 0.0274(6) Uani d . 1
H H14 0.4656 0.6259 0.3866 0.033 Uiso calc R 1
C C15 0.2162(5) 0.7226(5) 1.0062(3) 0.0416(8) Uani d . 1
H H15A 0.0937 0.6706 1.0029 0.062 Uiso calc R 1
H H15B 0.2633 0.8380 1.0409 0.062 Uiso calc R 1
H H15C 0.2745 0.6687 1.0538 0.062 Uiso calc R 1
C C16 0.4651(4) 1.0036(4) 0.6797(3) 0.0387(7) Uani d . 1
H H16A 0.3979 1.0671 0.6682 0.058 Uiso calc R 1
H H16B 0.4867 0.9730 0.6054 0.058 Uiso calc R 1
H H16C 0.5742 1.0693 0.7362 0.058 Uiso calc R 1
C C17 -0.1093(4) 0.1531(4) 0.6283(4) 0.0471(9) Uani d . 1
H H17A -0.1675 0.0368 0.6314 0.071 Uiso calc R 1
H H17B -0.1764 0.1801 0.5646 0.071 Uiso calc R 1
H H17C -0.0976 0.2176 0.7022 0.071 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_3
_geom_angle
C12 I O2 1_554 164.01(9)
O2 S C1 . 107.81(13)
O2 S C17 . 105.98(17)
C1 S C17 . 99.04(15)
C7 O1 C8 . 106.5(2)
C8 C1 C2 . 107.5(2)
C8 C1 S . 123.8(2)
C2 C1 S . 127.1(2)
C3 C2 C7 . 119.0(3)
C3 C2 C1 . 136.5(3)
C7 C2 C1 . 104.5(2)
C4 C3 C2 . 119.1(3)
C4 C3 H3 . 120.5
C2 C3 H3 . 120.5
C3 C4 C5 . 119.4(3)
C3 C4 C15 . 120.7(3)
C5 C4 C15 . 119.9(3)
C6 C5 C4 . 123.4(3)
C6 C5 H5 . 118.3
C4 C5 H5 . 118.3
C7 C6 C5 . 114.7(3)
C7 C6 C16 . 122.2(3)
C5 C6 C16 . 123.0(3)
O1 C7 C6 . 124.7(3)
O1 C7 C2 . 110.9(2)
C6 C7 C2 . 124.4(3)
C1 C8 O1 . 110.5(2)
C1 C8 C9 . 134.5(3)
O1 C8 C9 . 115.0(2)
C10 C9 C14 . 119.2(3)
C10 C9 C8 . 121.0(3)
C14 C9 C8 . 119.8(2)
C11 C10 C9 . 120.1(3)
C11 C10 H10 . 119.9
C9 C10 H10 . 119.9
C10 C11 C12 . 120.1(3)
C10 C11 H11 . 119.9
C12 C11 H11 . 119.9
C11 C12 C13 . 120.3(3)
C11 C12 I . 119.8(2)
C13 C12 I . 119.8(2)
C14 C13 C12 . 119.4(3)
C14 C13 H13 . 120.3
C12 C13 H13 . 120.3
C13 C14 C9 . 120.9(3)
C13 C14 H14 . 119.5
C9 C14 H14 . 119.5
C4 C15 H15A . 109.5
C4 C15 H15B . 109.5
H15A C15 H15B . 109.5
C4 C15 H15C . 109.5
H15A C15 H15C . 109.5
H15B C15 H15C . 109.5
C6 C16 H16A . 109.5
C6 C16 H16B . 109.5
H16A C16 H16B . 109.5
C6 C16 H16C . 109.5
H16A C16 H16C . 109.5
H16B C16 H16C . 109.5
S C17 H17A . 109.5
S C17 H17B . 109.5
H17A C17 H17B . 109.5
S 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
I C12 . 2.094(3)
I O2 1_554 3.145(2)
S O2 . 1.486(2)
S C1 . 1.766(3)
S C17 . 1.780(4)
O1 C7 . 1.379(3)
O1 C8 . 1.382(3)
C1 C8 . 1.364(4)
C1 C2 . 1.452(4)
C2 C3 . 1.391(4)
C2 C7 . 1.396(4)
C3 C4 . 1.385(4)
C3 H3 . 0.9300
C4 C5 . 1.409(4)
C4 C15 . 1.508(4)
C5 C6 . 1.385(4)
C5 H5 . 0.9300
C6 C7 . 1.385(4)
C6 C16 . 1.505(4)
C8 C9 . 1.459(4)
C9 C10 . 1.396(4)
C9 C14 . 1.404(4)
C10 C11 . 1.387(4)
C10 H10 . 0.9300
C11 C12 . 1.390(4)
C11 H11 . 0.9300
C12 C13 . 1.401(4)
C13 C14 . 1.378(4)
C13 H13 . 0.9300
C14 H14 . 0.9300
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 0.9600
C16 H16A . 0.9600
C16 H16B . 0.9600
C16 H16C . 0.9600
C17 H17A . 0.9600
C17 H17B . 0.9600
C17 H17C . 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
C16 H16B O1 . 0.96 2.55 2.975(4) 107.2 yes
C16 H16A O2 1_565 0.96 2.39 3.288(4) 155.5 yes
C17 H17B O1 2_566 0.96 2.51 3.422(4) 159.1 yes
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 S C1 C8 120.8(3)
C17 S C1 C8 -129.1(3)
O2 S C1 C2 -43.3(3)
C17 S C1 C2 66.8(3)
C8 C1 C2 C3 -178.7(3)
S C1 C2 C3 -12.5(5)
C8 C1 C2 C7 -0.5(3)
S C1 C2 C7 165.7(2)
C7 C2 C3 C4 -0.3(4)
C1 C2 C3 C4 177.8(3)
C2 C3 C4 C5 0.3(4)
C2 C3 C4 C15 -179.4(3)
C3 C4 C5 C6 -0.6(5)
C15 C4 C5 C6 179.1(3)
C4 C5 C6 C7 0.7(4)
C4 C5 C6 C16 -178.9(3)
C8 O1 C7 C6 178.1(3)
C8 O1 C7 C2 -0.7(3)
C5 C6 C7 O1 -179.4(3)
C16 C6 C7 O1 0.2(5)
C5 C6 C7 C2 -0.7(4)
C16 C6 C7 C2 178.9(3)
C3 C2 C7 O1 179.3(2)
C1 C2 C7 O1 0.7(3)
C3 C2 C7 C6 0.5(4)
C1 C2 C7 C6 -178.1(3)
C2 C1 C8 O1 0.1(3)
S C1 C8 O1 -166.67(19)
C2 C1 C8 C9 179.4(3)
S C1 C8 C9 12.6(5)
C7 O1 C8 C1 0.4(3)
C7 O1 C8 C9 -179.1(2)
C1 C8 C9 C10 27.6(5)
O1 C8 C9 C10 -153.1(3)
C1 C8 C9 C14 -153.4(3)
O1 C8 C9 C14 25.9(4)
C14 C9 C10 C11 0.8(4)
C8 C9 C10 C11 179.8(3)
C9 C10 C11 C12 -0.8(4)
C10 C11 C12 C13 0.4(4)
C10 C11 C12 I -175.5(2)
C11 C12 C13 C14 -0.1(4)
I C12 C13 C14 175.8(2)
C12 C13 C14 C9 0.2(4)
C10 C9 C14 C13 -0.5(4)
C8 C9 C14 C13 -179.5(3)
