#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/91/2009123.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_2009123
loop_
_publ_author_name
'Luck, Rudy L.'
'Bates, Dallas K.'
'Li, Kexue'
'Xia, Mingde'
_publ_section_title
;
 1-[(1,3-Dihydro-2-benzothienyl)acetyl]-1<i>H</i>-indole <i>S</i>-oxide
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1873
_journal_page_last               1874
_journal_paper_doi               10.1107/S0108270199010148
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C18 H15 N1 O2 S1'
_chemical_formula_sum            'C18 H15 N O2 S'
_chemical_formula_weight         309.38
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.716(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9630(10)
_cell_length_b                   10.458(2)
_cell_length_c                   28.310(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.96
_cell_measurement_theta_min      8.19
_cell_volume                     1464.4(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'non-profiled \w'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            3739
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.104
_reflns_number_gt                2802
_reflns_number_total             3355
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fr1217.cif
_cod_data_source_block           li1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C18 H15 N1 O2 S1'
_cod_database_code               2009123
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_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
_atom_site_type_symbol
S1 .50980(7) .17687(3) .788268(13) .03833(12) Uani d . 1 . . S
O1 .7378(2) .08737(10) .78014(4) .0492(3) Uani d . 1 . . O
O2 .3924(2) .24542(13) .68763(4) .0559(3) Uani d . 1 . . O
N1 .6739(2) .35455(12) .64269(4) .0368(3) Uani d . 1 . . N
C1 .5610(3) .31574(14) .59739(5) .0375(3) Uani d . 1 . . C
C2 .3585(3) .22722(18) .58433(6) .0490(4) Uani d . 1 . . C
C3 .3003(4) .2062(2) .53620(7) .0612(5) Uani d . 1 . . C
C4 .4351(4) .2713(2) .50231(7) .0667(5) Uani d . 1 . . C
C5 .6344(4) .3583(2) .51555(6) .0620(5) Uani d . 1 . . C
C6 .7003(3) .38168(16) .56387(5) .0450(3) Uani d . 1 . . C
C7 .8967(4) .46254(18) .58937(6) .0521(4) Uani d . 1 . . C
C8 .8803(3) .44357(15) .63593(5) .0418(3) Uani d . 1 . . C
C9 .5930(3) .31122(14) .68602(5) .0371(3) Uani d . 1 . . C
C10 .7732(3) .34529(15) .72970(5) .0366(3) Uani d . 1 . . C
C11 .6281(3) .33994(12) .77508(5) .0323(3) Uani d . 1 . . C
C12 .8019(3) .38106(13) .81888(5) .0324(3) Uani d . 1 . . C
C13 .9961(3) .47737(14) .82087(5) .0399(3) Uani d . 1 . . C
C14 1.1383(4) .50552(16) .86395(6) .0482(4) Uani d . 1 . . C
C15 1.0858(4) .43963(17) .90480(6) .0499(4) Uani d . 1 . . C
C16 .8926(3) .34331(17) .90289(5) .0459(4) Uani d . 1 . . C
C17 .7515(3) .31340(13) .85982(5) .0363(3) Uani d . 1 . . C
C18 .5374(3) .21258(16) .85146(5) .0426(3) Uani d . 1 . . C
H2 .261(4) .1873(19) .6065(7) .056(5) Uiso d . 1 . . H
H3 .156(4) .143(2) .5263(8) .070(6) Uiso d . 1 . . H
H4 .394(5) .258(2) .4701(9) .077(7) Uiso d . 1 . . H
H5 .734(4) .402(2) .4923(8) .068(6) Uiso d . 1 . . H
H7 1.019(4) .517(2) .5760(8) .069(6) Uiso d . 1 . . H
H8 .974(4) .4820(18) .6622(7) .053(5) Uiso d . 1 . . H
H11 .462(3) .3887(15) .7701(5) .034(4) Uiso d . 1 . . H
H13 1.030(3) .5278(19) .7927(6) .054(5) Uiso d . 1 . . H
H14 1.267(4) .568(2) .8651(7) .064(6) Uiso d . 1 . . H
H15 1.185(4) .4615(19) .9329(7) .057(5) Uiso d . 1 . . H
H16 .860(4) .2963(19) .9314(7) .056(5) Uiso d . 1 . . H
H101 .846(3) .4289(19) .7262(6) .050(5) Uiso d . 1 . . H
H102 .923(4) .2872(18) .7305(6) .050(5) Uiso d . 1 . . H
H181 .579(4) .129(2) .8687(7) .062(5) Uiso d . 1 . . H
H182 .366(4) .239(2) .8581(7) .064(6) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 .03805(19) .03557(19) .0415(2) -.00532(13) .00410(14) .00195(13)
O1 .0642(7) .0353(5) .0491(6) .0097(5) .0101(5) -.0001(4)
O2 .0544(7) .0712(8) .0414(6) -.0248(6) .0006(5) .0020(5)
N1 .0390(6) .0394(6) .0319(6) -.0009(5) .0014(5) .0002(5)
C1 .0386(7) .0409(7) .0327(6) .0072(6) -.0001(5) .0001(5)
C2 .0478(8) .0566(10) .0416(8) -.0037(7) -.0026(7) -.0016(7)
C3 .0576(10) .0743(12) .0495(10) -.0055(10) -.0085(8) -.0111(9)
C4 .0697(12) .0927(15) .0363(8) .0007(11) -.0037(8) -.0096(9)
C5 .0672(11) .0854(13) .0341(8) -.0032(10) .0085(8) .0021(8)
C6 .0483(8) .0521(9) .0351(7) .0046(7) .0062(6) .0018(6)
C7 .0554(9) .0585(10) .0437(8) -.0111(8) .0118(7) .0041(7)
C8 .0433(8) .0418(8) .0405(7) -.0042(6) .0053(6) -.0003(6)
C9 .0389(7) .0376(7) .0348(7) -.0017(6) .0038(5) .0012(5)
C10 .0366(7) .0413(8) .0320(7) -.0027(6) .0035(5) .0013(5)
C11 .0322(6) .0305(6) .0344(6) .0025(5) .0045(5) .0021(5)
C12 .0354(6) .0310(6) .0313(6) .0046(5) .0056(5) -.0009(5)
C13 .0484(8) .0324(7) .0393(7) -.0017(6) .0051(6) .0000(6)
C14 .0555(9) .0382(8) .0501(9) -.0066(7) -.0008(7) -.0072(7)
C15 .0594(10) .0503(9) .0386(8) .0044(8) -.0044(7) -.0083(7)
C16 .0555(9) .0502(9) .0325(7) .0071(7) .0067(6) .0008(6)
C17 .0383(7) .0365(7) .0352(7) .0042(6) .0096(5) .0007(5)
C18 .0440(8) .0445(8) .0410(7) -.0013(7) .0148(6) .0049(6)
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 -2 6
-2 -2 4
-1 -5 3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 C18 106.37(7)
O1 S1 C11 106.73(8)
C18 S1 C11 90.55(7)
C9 N1 C8 126.74(12)
C9 N1 C1 125.54(12)
C8 N1 C1 107.71(12)
C2 C1 C6 122.19(14)
C2 C1 N1 130.81(14)
C6 C1 N1 106.97(13)
C3 C2 C1 116.96(17)
C2 C3 C4 121.75(19)
C5 C4 C3 120.83(17)
C4 C5 C6 119.14(18)
C1 C6 C5 119.13(16)
C1 C6 C7 107.54(14)
C5 C6 C7 133.32(16)
C8 C7 C6 108.21(15)
C7 C8 N1 109.55(14)
O2 C9 N1 120.83(13)
O2 C9 C10 122.41(13)
N1 C9 C10 116.71(12)
C9 C10 C11 113.14(13)
C12 C11 C10 113.78(12)
C12 C11 S1 105.38(9)
C10 C11 S1 112.53(10)
C13 C12 C17 120.20(13)
C13 C12 C11 125.79(12)
C17 C12 C11 114.01(12)
C14 C13 C12 119.27(14)
C15 C14 C13 120.59(16)
C16 C15 C14 120.25(15)
C15 C16 C17 119.56(14)
C16 C17 C12 120.11(14)
C16 C17 C18 126.49(14)
C12 C17 C18 113.39(13)
C17 C18 S1 107.09(10)
C1 C2 H2 121.8(13)
C3 C2 H2 121.1(13)
C2 C3 H3 117.9(13)
C4 C3 H3 120.4(13)
C3 C4 H4 121.6(15)
C5 C4 H4 117.6(15)
C4 C5 H5 121.6(13)
C6 C5 H5 119.2(13)
C6 C7 H7 126.3(14)
C8 C7 H7 125.4(14)
N1 C8 H8 119.8(12)
C7 C8 H8 130.6(12)
C9 C10 H101 109.7(11)
C9 C10 H102 106.0(11)
C11 C10 H101 109.3(11)
C11 C10 H102 112.1(11)
H101 C10 H102 106.3(16)
C10 C11 H11 108.2(9)
C12 C11 H11 113.0(9)
C12 C13 H13 121.4(11)
C14 C13 H13 119.3(11)
C13 C14 H14 119.2(13)
C15 C14 H14 120.2(13)
C14 C15 H15 117.9(12)
C16 C15 H15 121.9(12)
C15 C16 H16 119.7(12)
C17 C16 H16 120.7(12)
C17 C18 H181 114.6(12)
C17 C18 H182 114.0(13)
H181 C18 H182 108.2(17)
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
S1 O1 . 1.5007(15) ?
S1 C18 . 1.8217(16) ?
S1 C11 . 1.8516(16) ?
O2 C9 . 1.214(2) ?
N1 C9 . 1.3970(18) ?
N1 C8 . 1.409(2) ?
N1 C1 . 1.4161(18) ?
C1 C2 . 1.394(2) ?
C1 C6 . 1.400(2) ?
C2 C3 . 1.387(2) ?
C3 C4 . 1.392(3) ?
C4 C5 . 1.373(3) ?
C5 C6 . 1.402(2) ?
C6 C7 . 1.439(2) ?
C7 C8 . 1.342(2) ?
C9 C10 . 1.508(2) ?
C10 C11 . 1.5247(19) ?
C11 C12 . 1.5133(19) ?
C12 C13 . 1.392(2) ?
C12 C17 . 1.3978(19) ?
C13 C14 . 1.389(2) ?
C14 C15 . 1.389(2) ?
C15 C16 . 1.389(3) ?
C16 C17 . 1.391(2) ?
C17 C18 . 1.502(2) ?
C2 H2 . .92(2) ?
C3 H3 . 1.00(3) ?
C4 H4 . .93(3) ?
C5 H5 . .97(3) ?
C7 H7 . .94(3) ?
C8 H8 . .935(19) ?
C10 H101 . .96(2) ?
C10 H102 . .960(19) ?
C11 H11 . .970(16) ?
C13 H13 . .982(19) ?
C14 H14 . .91(3) ?
C15 H15 . .93(2) ?
C16 H16 . .97(3) ?
C18 H181 . 1.01(3) ?
C18 H182 . .93(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21105640
2 PubChem 139056891