#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/88/2218800.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_2218800
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Isopropyl-2-methyl-3-phenylsulfonyl-1-benzofuran
;
_journal_coeditor_code           RT2021
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1257
_journal_paper_doi               10.1107/S1600536808017224
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H18 O3 S'
_chemical_formula_moiety         'C18 H18 O3 S'
_chemical_formula_sum            'C18 H18 O3 S'
_chemical_formula_weight         314.38
_chemical_melting_point_gt       386
_chemical_melting_point_lt       387
_chemical_name_systematic
;
5-Isopropyl-2-methyl-3-phenylsulfonyl-1-benzofuran
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.655(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7360(10)
_cell_length_b                   13.0240(10)
_cell_length_c                   11.7290(10)
_cell_measurement_reflns_used    5849
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.36
_cell_volume                     1616.8(2)
_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      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 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  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9705
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.527
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0486
_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)+(0.061P)²+1.3518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                3008
_reflns_number_total             3505
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rt2021.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218800
_cod_database_fobs_code          2218800
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.83554(4) 0.69176(3) 0.55320(4) 0.02524(15) Uani d . 1
O O1 0.46657(13) 0.66684(10) 0.47014(12) 0.0288(3) Uani d . 1
O O2 0.84305(15) 0.79303(10) 0.60360(13) 0.0360(4) Uani d . 1
O O3 0.90954(14) 0.66788(11) 0.46512(12) 0.0328(3) Uani d . 1
C C1 0.67826(18) 0.66590(13) 0.49602(15) 0.0239(4) Uani d . 1
C C2 0.63435(17) 0.58971(13) 0.40821(15) 0.0224(4) Uani d . 1
C C3 0.68980(17) 0.52023(13) 0.34157(16) 0.0247(4) Uani d . 1
H H3 0.7791 0.5153 0.3493 0.030 Uiso calc R 1
C C4 0.61150(18) 0.45785(14) 0.26310(17) 0.0273(4) Uani d . 1
C C5 0.47968(19) 0.46738(15) 0.25280(17) 0.0294(4) Uani d . 1
H H5 0.4275 0.4251 0.1986 0.035 Uiso calc R 1
C C6 0.42262(18) 0.53572(14) 0.31820(17) 0.0285(4) Uani d . 1
H H6 0.3334 0.5417 0.3101 0.034 Uiso calc R 1
C C7 0.50303(17) 0.59463(13) 0.39592(15) 0.0241(4) Uani d . 1
C C8 0.5751(2) 0.70820(14) 0.53031(17) 0.0285(4) Uani d . 1
C C9 0.87264(17) 0.60205(13) 0.66639(15) 0.0231(4) Uani d . 1
C C10 0.85507(18) 0.62898(15) 0.77698(16) 0.0287(4) Uani d . 1
H H10 0.8269 0.6959 0.7924 0.034 Uiso calc R 1
C C11 0.8793(2) 0.55655(17) 0.86501(17) 0.0330(4) Uani d . 1
H H11 0.8657 0.5732 0.9408 0.040 Uiso calc R 1
C C12 0.92341(19) 0.45979(16) 0.84182(18) 0.0327(4) Uani d . 1
H H12 0.9401 0.4105 0.9022 0.039 Uiso calc R 1
C C13 0.94327(18) 0.43436(15) 0.73172(17) 0.0300(4) Uani d . 1
H H13 0.9752 0.3684 0.7172 0.036 Uiso calc R 1
C C14 0.91658(17) 0.50522(14) 0.64226(16) 0.0255(4) Uani d . 1
H H14 0.9281 0.4879 0.5661 0.031 Uiso calc R 1
C C15 0.6668(2) 0.38118(17) 0.1882(2) 0.0391(5) Uani d . 1
H H15 0.5962 0.3356 0.1517 0.047 Uiso calc R 1
C C16 0.7664(3) 0.3128(2) 0.2585(3) 0.0692(9) Uani d . 1
H H16A 0.7283 0.2745 0.3158 0.083 Uiso calc R 1
H H16B 0.8356 0.3554 0.2982 0.083 Uiso calc R 1
H H16C 0.7993 0.2645 0.2068 0.083 Uiso calc R 1
C C17 0.7186(3) 0.4350(2) 0.0905(3) 0.0668(9) Uani d . 1
H H17A 0.7851 0.4833 0.1234 0.080 Uiso calc R 1
H H17B 0.6503 0.4725 0.0420 0.080 Uiso calc R 1
H H17C 0.7538 0.3839 0.0435 0.080 Uiso calc R 1
C C18 0.5557(2) 0.78612(17) 0.6181(2) 0.0409(5) Uani d . 1
H H18A 0.6374 0.8155 0.6525 0.061 Uiso calc R 1
H H18B 0.5166 0.7536 0.6786 0.061 Uiso calc R 1
H H18C 0.5004 0.8407 0.5810 0.061 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
O3 S O2 119.50(9)
O3 S C1 107.34(9)
O2 S C1 108.58(9)
O3 S C9 108.37(9)
O2 S C9 107.90(9)
C1 S C9 104.11(8)
C8 O1 C7 106.6(2)
C8 C1 C2 107.7(2)
C8 C1 S 126.5(2)
C2 C1 S 125.70(10)
C7 C2 C3 119.5(2)
C7 C2 C1 104.2(2)
C3 C2 C1 136.4(2)
C2 C3 C4 118.7(2)
C2 C3 H3 120.6
C4 C3 H3 120.6
C5 C4 C3 119.4(2)
C5 C4 C15 119.7(2)
C3 C4 C15 120.9(2)
C6 C5 C4 122.8(2)
C6 C5 H5 118.6
C4 C5 H5 118.6
C5 C6 C7 116.0(2)
C5 C6 H6 122.0
C7 C6 H6 122.0
C6 C7 O1 125.7(2)
C6 C7 C2 123.6(2)
O1 C7 C2 110.8(2)
C1 C8 O1 110.8(2)
C1 C8 C18 134.4(2)
O1 C8 C18 114.9(2)
C10 C9 C14 121.6(2)
C10 C9 S 119.20(10)
C14 C9 S 119.30(10)
C9 C10 C11 119.0(2)
C9 C10 H10 120.5
C11 C10 H10 120.5
C10 C11 C12 119.8(2)
C10 C11 H11 120.1
C12 C11 H11 120.1
C13 C12 C11 120.7(2)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 120.1(2)
C12 C13 H13 120.0
C14 C13 H13 120.0
C13 C14 C9 118.8(2)
C13 C14 H14 120.6
C9 C14 H14 120.6
C4 C15 C16 112.2(2)
C4 C15 C17 111.1(2)
C16 C15 C17 111.4(3)
C4 C15 H15 107.3
C16 C15 H15 107.3
C17 C15 H15 107.3
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C8 C18 H18A 109.5
C8 C18 H18B 109.5
H18A C18 H18B 109.5
C8 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S O3 1.439(2)
S O2 1.4420(10)
S C1 1.742(2)
S C9 1.763(2)
O1 C8 1.367(2)
O1 C7 1.382(2)
C1 C8 1.357(3)
C1 C2 1.451(2)
C2 C7 1.394(3)
C2 C3 1.393(3)
C3 C4 1.398(3)
C3 H3 0.9500
C4 C5 1.406(3)
C4 C15 1.515(3)
C5 C6 1.383(3)
C5 H5 0.9500
C6 C7 1.379(3)
C6 H6 0.9500
C8 C18 1.485(3)
C9 C10 1.387(3)
C9 C14 1.392(3)
C10 C11 1.390(3)
C10 H10 0.9500
C11 C12 1.389(3)
C11 H11 0.9500
C12 C13 1.384(3)
C12 H12 0.9500
C13 C14 1.391(3)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.524(4)
C15 C17 1.525(4)
C15 H15 1.0000
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 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 Cg3 3_666 0.95 2.65 3.516(3) 151.9
C18 H18A O2 . 0.98 2.39 3.119(3) 130.7
C10 H10 O2 . 0.95 2.58 2.938(2) 102.6
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
O3 S C1 C8 -155.70(16)
O2 S C1 C8 -25.23(19)
C9 S C1 C8 89.53(18)
O3 S C1 C2 28.81(17)
O2 S C1 C2 159.29(15)
C9 S C1 C2 -85.95(16)
C8 C1 C2 C7 0.97(19)
S C1 C2 C7 177.16(13)
C8 C1 C2 C3 -178.7(2)
S C1 C2 C3 -2.5(3)
C7 C2 C3 C4 0.6(3)
C1 C2 C3 C4 -179.76(19)
C2 C3 C4 C5 0.5(3)
C2 C3 C4 C15 179.81(18)
C3 C4 C5 C6 -0.7(3)
C15 C4 C5 C6 -179.93(19)
C4 C5 C6 C7 -0.4(3)
C5 C6 C7 O1 -179.49(16)
C5 C6 C7 C2 1.6(3)
C8 O1 C7 C6 -179.09(17)
C8 O1 C7 C2 -0.08(19)
C3 C2 C7 C6 -1.8(3)
C1 C2 C7 C6 178.49(17)
C3 C2 C7 O1 179.20(15)
C1 C2 C7 O1 -0.54(19)
C2 C1 C8 O1 -1.1(2)
S C1 C8 O1 -177.24(12)
C2 C1 C8 C18 177.6(2)
S C1 C8 C18 1.5(3)
C7 O1 C8 C1 0.7(2)
C7 O1 C8 C18 -178.25(16)
O3 S C9 C10 154.95(15)
O2 S C9 C10 24.22(18)
C1 S C9 C10 -91.01(16)
O3 S C9 C14 -26.26(17)
O2 S C9 C14 -156.99(14)
C1 S C9 C14 87.77(16)
C14 C9 C10 C11 -1.5(3)
S C9 C10 C11 177.28(15)
C9 C10 C11 C12 1.6(3)
C10 C11 C12 C13 -0.2(3)
C11 C12 C13 C14 -1.3(3)
C12 C13 C14 C9 1.4(3)
C10 C9 C14 C13 0.0(3)
S C9 C14 C13 -178.78(14)
C5 C4 C15 C16 -129.9(2)
C3 C4 C15 C16 50.8(3)
C5 C4 C15 C17 104.7(2)
C3 C4 C15 C17 -74.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740220
