#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:49:58 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239503.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_2239503
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 5-Cyclopentyl-2-methyl-3-(4-methylphenylsulfonyl)-1-benzofuran
;
_journal_coeditor_code           BT6977
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o592
_journal_paper_doi               10.1107/S160053681400868X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C21 H22 O3 S'
_chemical_formula_moiety         'C21 H22 O3 S'
_chemical_formula_sum            'C21 H22 O3 S'
_chemical_formula_weight         354.45
_chemical_melting_point_gt       399
_chemical_melting_point_lt       398
_chemical_name_systematic
;
5-Cyclopentyl-2-methyl-3-(4-methylphenylsulfonyl)-1-benzofuran
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 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                90.00
_cell_angle_beta                 91.626(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5452(7)
_cell_length_b                   6.3093(4)
_cell_length_c                   13.7813(9)
_cell_measurement_reflns_used    4626
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.65
_cell_measurement_theta_min      2.40
_cell_volume                     916.54(10)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) 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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graphite multilayer'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13479
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.187
_refine_ls_abs_structure_details 'Flack (1983), 2111 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4144
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0430
_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)+(0.0577P)²+0.0503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                3276
_reflns_number_total             4144
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6977sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               2239503
_cod_database_fobs_code          2239503
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, 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
_atom_site_symmetry_multiplicity
S S1 0.50057(4) 0.43392(9) 0.52665(4) 0.04206(17) Uani d . 1 2
O O1 0.81242(17) 0.5370(3) 0.38708(14) 0.0529(5) Uani d . 1 2
O O2 0.46721(17) 0.2152(3) 0.53932(12) 0.0487(5) Uani d . 1 2
O O3 0.52795(18) 0.5621(3) 0.61028(12) 0.0545(5) Uani d . 1 2
C C1 0.6301(2) 0.4397(4) 0.45279(16) 0.0398(6) Uani d . 1 2
C C2 0.6569(2) 0.2858(4) 0.37834(16) 0.0376(5) Uani d . 1 2
C C3 0.5997(2) 0.1062(4) 0.34016(15) 0.0384(5) Uani d . 1 2
H H3 0.5220 0.0571 0.3652 0.046 Uiso calc R 1 2
C C4 0.6558(2) -0.0023(4) 0.26530(16) 0.0413(5) Uani d . 1 2
C C5 0.7737(2) 0.0714(5) 0.23120(18) 0.0509(7) Uani d . 1 2
H H5 0.8134 -0.0044 0.1809 0.061 Uiso calc R 1 2
C C6 0.8315(3) 0.2481(5) 0.2687(2) 0.0549(7) Uani d . 1 2
H H6 0.9104 0.2961 0.2454 0.066 Uiso calc R 1 2
C C7 0.7714(2) 0.3539(4) 0.34139(17) 0.0454(6) Uani d . 1 2
C C8 0.7251(2) 0.5865(4) 0.45435(18) 0.0461(6) Uani d . 1 2
C C9 0.5876(3) -0.1898(4) 0.22067(17) 0.0484(7) Uani d . 1 2
H H9 0.5692 -0.2910 0.2743 0.058 Uiso calc R 1 2
C C10 0.6516(3) -0.3141(5) 0.1417(2) 0.0678(9) Uani d . 1 2
H H10A 0.6880 -0.2181 0.0930 0.081 Uiso calc R 1 2
H H10B 0.7198 -0.4056 0.1693 0.081 Uiso calc R 1 2
C C11 0.5457(3) -0.4451(5) 0.0973(3) 0.0762(10) Uani d . 1 2
H H11A 0.5624 -0.4774 0.0286 0.091 Uiso calc R 1 2
H H11B 0.5366 -0.5801 0.1331 0.091 Uiso calc R 1 2
C C12 0.4278(4) -0.3131(6) 0.1049(3) 0.0920(12) Uani d . 1 2
H H12A 0.3581 -0.3981 0.1319 0.110 Uiso calc R 1 2
H H12B 0.4001 -0.2596 0.0401 0.110 Uiso calc R 1 2
C C13 0.4621(3) -0.1308(6) 0.1718(3) 0.0729(9) Uani d . 1 2
H H13A 0.3962 -0.1109 0.2207 0.087 Uiso calc R 1 2
H H13B 0.4704 0.0022 0.1345 0.087 Uiso calc R 1 2
C C14 0.7537(3) 0.7785(5) 0.5121(2) 0.0636(8) Uani d . 1 2
H H14A 0.8248 0.7497 0.5575 0.095 Uiso calc R 1 2
H H14B 0.6789 0.8187 0.5485 0.095 Uiso calc R 1 2
H H14C 0.7764 0.8945 0.4686 0.095 Uiso calc R 1 2
C C15 0.3770(2) 0.5572(4) 0.45880(16) 0.0404(6) Uani d . 1 2
C C16 0.3159(2) 0.4485(4) 0.38343(19) 0.0461(6) Uani d . 1 2
H H16 0.3406 0.3077 0.3684 0.055 Uiso calc R 1 2
C C17 0.2205(3) 0.5442(4) 0.3310(2) 0.0539(7) Uani d . 1 2
H H17 0.1786 0.4687 0.2798 0.065 Uiso calc R 1 2
C C18 0.1836(2) 0.7506(4) 0.3514(2) 0.0500(6) Uani d . 1 2
C C19 0.2460(3) 0.8554(4) 0.4268(2) 0.0526(7) Uani d . 1 2
H H19 0.2212 0.9958 0.4424 0.063 Uiso calc R 1 2
C C20 0.3435(3) 0.7610(4) 0.47994(19) 0.0478(6) Uani d . 1 2
H H20 0.3868 0.8365 0.5305 0.057 Uiso calc R 1 2
C C21 0.0784(3) 0.8560(6) 0.2938(3) 0.0746(9) Uani d . 1 2
H H21A 0.1139 0.9335 0.2393 0.112 Uiso calc R 1 2
H H21B 0.0337 0.9552 0.3356 0.112 Uiso calc R 1 2
H H21C 0.0188 0.7483 0.2691 0.112 Uiso calc R 1 2
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 S1 O2 119.33(11)
O3 S1 C1 108.55(11)
O2 S1 C1 107.01(11)
O3 S1 C15 107.88(11)
O2 S1 C15 107.98(11)
C1 S1 C15 105.24(11)
C8 O1 C7 107.06(19)
C8 C1 C2 108.0(2)
C8 C1 S1 126.7(2)
C2 C1 S1 125.30(17)
C3 C2 C7 119.2(2)
C3 C2 C1 136.8(2)
C7 C2 C1 104.0(2)
C2 C3 C4 119.9(2)
C2 C3 H3 120.1
C4 C3 H3 120.1
C3 C4 C5 118.8(3)
C3 C4 C9 118.9(2)
C5 C4 C9 122.3(2)
C6 C5 C4 121.9(3)
C6 C5 H5 119.1
C4 C5 H5 119.1
C5 C6 C7 117.6(3)
C5 C6 H6 121.2
C7 C6 H6 121.2
C6 C7 O1 126.5(2)
C6 C7 C2 122.6(3)
O1 C7 C2 110.8(2)
O1 C8 C1 110.2(2)
O1 C8 C14 115.0(2)
C1 C8 C14 134.8(3)
C4 C9 C13 112.9(2)
C4 C9 C10 118.9(3)
C13 C9 C10 102.1(2)
C4 C9 H9 107.5
C13 C9 H9 107.5
C10 C9 H9 107.5
C11 C10 C9 103.6(3)
C11 C10 H10A 111.0
C9 C10 H10A 111.0
C11 C10 H10B 111.0
C9 C10 H10B 111.0
H10A C10 H10B 109.0
C12 C11 C10 105.9(3)
C12 C11 H11A 110.6
C10 C11 H11A 110.6
C12 C11 H11B 110.6
C10 C11 H11B 110.6
H11A C11 H11B 108.7
C11 C12 C13 106.2(3)
C11 C12 H12A 110.5
C13 C12 H12A 110.5
C11 C12 H12B 110.5
C13 C12 H12B 110.5
H12A C12 H12B 108.7
C12 C13 C9 106.0(3)
C12 C13 H13A 110.5
C9 C13 H13A 110.5
C12 C13 H13B 110.5
C9 C13 H13B 110.5
H13A C13 H13B 108.7
C8 C14 H14A 109.5
C8 C14 H14B 109.5
H14A C14 H14B 109.5
C8 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C20 C15 C16 120.5(2)
C20 C15 S1 119.57(18)
C16 C15 S1 119.94(19)
C17 C16 C15 119.8(2)
C17 C16 H16 120.1
C15 C16 H16 120.1
C16 C17 C18 121.0(2)
C16 C17 H17 119.5
C18 C17 H17 119.5
C19 C18 C17 118.0(2)
C19 C18 C21 120.9(3)
C17 C18 C21 121.0(3)
C20 C19 C18 121.6(3)
C20 C19 H19 119.2
C18 C19 H19 119.2
C15 C20 C19 119.1(2)
C15 C20 H20 120.5
C19 C20 H20 120.5
C18 C21 H21A 109.5
C18 C21 H21B 109.5
H21A C21 H21B 109.5
C18 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4307(17)
S1 O2 1.4358(18)
S1 C1 1.727(2)
S1 C15 1.763(2)
O1 C8 1.362(3)
O1 C7 1.379(3)
C1 C8 1.364(3)
C1 C2 1.446(3)
C2 C3 1.381(3)
C2 C7 1.392(3)
C3 C4 1.385(3)
C3 H3 0.9500
C4 C5 1.419(4)
C4 C9 1.507(4)
C5 C6 1.365(4)
C5 H5 0.9500
C6 C7 1.373(4)
C6 H6 0.9500
C8 C14 1.476(4)
C9 C13 1.514(4)
C9 C10 1.515(4)
C9 H9 1.0000
C10 C11 1.505(5)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.502(5)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.512(4)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 C20 1.367(3)
C15 C16 1.388(3)
C16 C17 1.363(4)
C16 H16 0.9500
C17 C18 1.390(4)
C17 H17 0.9500
C18 C19 1.383(4)
C18 C21 1.501(4)
C19 C20 1.381(4)
C19 H19 0.9500
C20 H20 0.9500
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 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 O3 2_564 0.95 2.44 3.279(3) 147.7
C20 H20 O2 1_565 0.95 2.54 3.244(3) 131.3
C9 H9 Cg1 1_545 1.0 2.89 3.680(3) 135.5
C12 H12B Cg1 2_454 0.99 2.88 3.591(3) 129.0
C14 H14C Cg2 1_565 0.98 2.94 3.826(3) 150.6
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 S1 C1 C8 -19.1(2)
O2 S1 C1 C8 -149.1(2)
C15 S1 C1 C8 96.2(2)
O3 S1 C1 C2 160.22(18)
O2 S1 C1 C2 30.2(2)
C15 S1 C1 C2 -84.5(2)
C8 C1 C2 C3 -178.8(2)
S1 C1 C2 C3 1.8(4)
C8 C1 C2 C7 1.1(2)
S1 C1 C2 C7 -178.34(17)
C7 C2 C3 C4 -0.7(3)
C1 C2 C3 C4 179.2(2)
C2 C3 C4 C5 1.7(3)
C2 C3 C4 C9 -176.2(2)
C3 C4 C5 C6 -1.4(3)
C9 C4 C5 C6 176.5(2)
C4 C5 C6 C7 0.0(4)
C5 C6 C7 O1 -178.5(2)
C5 C6 C7 C2 1.1(4)
C8 O1 C7 C6 -179.8(2)
C8 O1 C7 C2 0.6(2)
C3 C2 C7 C6 -0.8(3)
C1 C2 C7 C6 179.3(2)
C3 C2 C7 O1 178.86(19)
C1 C2 C7 O1 -1.0(2)
C7 O1 C8 C1 0.2(2)
C7 O1 C8 C14 179.3(2)
C2 C1 C8 O1 -0.8(3)
S1 C1 C8 O1 178.63(16)
C2 C1 C8 C14 -179.7(3)
S1 C1 C8 C14 -0.3(4)
C3 C4 C9 C13 63.1(3)
C5 C4 C9 C13 -114.8(3)
C3 C4 C9 C10 -177.4(2)
C5 C4 C9 C10 4.7(3)
C4 C9 C10 C11 -165.3(2)
C13 C9 C10 C11 -40.4(3)
C9 C10 C11 C12 32.6(4)
C10 C11 C12 C13 -11.8(4)
C11 C12 C13 C9 -13.6(4)
C4 C9 C13 C12 162.1(3)
C10 C9 C13 C12 33.3(4)
O3 S1 C15 C20 12.7(2)
O2 S1 C15 C20 142.91(19)
C1 S1 C15 C20 -103.1(2)
O3 S1 C15 C16 -168.37(19)
O2 S1 C15 C16 -38.1(2)
C1 S1 C15 C16 75.9(2)
C20 C15 C16 C17 -1.0(4)
S1 C15 C16 C17 -180.0(2)
C15 C16 C17 C18 0.5(4)
C16 C17 C18 C19 -0.4(4)
C16 C17 C18 C21 -179.9(3)
C17 C18 C19 C20 1.0(4)
C21 C18 C19 C20 -179.6(3)
C16 C15 C20 C19 1.5(4)
S1 C15 C20 C19 -179.5(2)
C18 C19 C20 C15 -1.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086637
