#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/12/7241236.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7241236
loop_
_publ_author_name
'Shen, Jinhui'
'Yu, Aimin'
'Zhang, Lei'
'Meng, Xiangtai'
_publ_section_title
;
 Construction of benzothiophene fused pyrrolidone in water via a
 catalyst-free process and a mechanism study
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              6798
_journal_page_last               6803
_journal_paper_doi               10.1039/D0GC01860K
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C19 H17 N O2 S'
_chemical_formula_sum            'C19 H17 N O2 S'
_chemical_formula_weight         323.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-06 deposited with the CCDC.	2020-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.96320(10)
_cell_length_b                   9.9037(3)
_cell_length_c                   33.6030(9)
_cell_measurement_reflns_used    2747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.2070
_cell_measurement_theta_min      2.6140
_cell_volume                     1651.72(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  45.00   0.50    0.80    --   40.90 -43.00  30.00   52
  2  ω    -49.00  12.00   0.50    0.80    --   40.90 -43.00-180.00  122
  3  ω     18.00  72.00   0.50    0.80    --   40.90 -43.00-180.00  108
  4  ω    -49.00   1.00   0.50    0.80    --   40.90 -82.00 -60.00  100
  5  ω    -49.00  13.00   0.50    0.80    --   40.90 -43.00  30.00  124
  6  ω     25.00  67.00   0.50    0.80    --   40.90 -82.00  90.00   84
  7  ω     -1.00  66.00   0.50    0.80    --   40.90 -82.00  30.00  134
  8  ω     30.00  66.00   0.50    0.80    --   40.90 -82.00 -30.00   72
  9  ω    -30.00   2.00   0.50    0.80    --   40.90 -82.00  90.00   64
 10  ω     14.00  48.00   0.50    0.80    --   40.90 -82.00 -60.00   68
 11  ω    -27.00   6.00   0.50    0.80    --   40.90 -82.00 -30.00   66
 12  ω     50.00  75.00   0.50    0.80    --   40.90 -43.00  30.00   50
 13  ω    -33.00  -7.00   0.50    0.80    --   40.90 -65.00-180.00   52
 14  ω      4.00  52.00   0.50    0.80    --   40.90 -65.00-180.00   96
 15  ω    -49.00  35.00   0.50    0.80    --   40.90 -77.00 150.00  168
 16  ω     27.00  68.00   0.50    0.80    --   40.90 -82.00-180.00   82
 17  ω     33.00  64.00   0.50    0.80    --   40.90  54.00  30.00   62
 18  ω    -21.00  14.00   0.50    0.80    --   40.90 -65.00 -30.00   70
 19  ω      6.00 122.00   0.50    0.80    --   93.40 -50.00 -60.00  232
 20  ω     18.00  92.00   0.50    0.80    --   93.40 -33.00 -60.00  148
 21  ω    132.00 181.00   0.50    0.80    --   93.40  82.00-120.00   98
 22  ω     13.00  64.00   0.50    0.80    --   93.40 -77.00 -90.00  102
 23  ω     66.00  95.00   0.50    0.80    --   93.40  82.00-120.00   58
 24  ω     16.00  94.00   0.50    0.80    --   93.40 -82.00-180.00  156
 25  ω    147.00 183.00   0.50    0.80    --   93.40  59.00   0.00   72
 26  ω    111.00 137.00   0.50    0.80    --   93.40  59.00   0.00   52
 27  ω      4.00  98.00   0.50    0.80    --   93.40 -82.00-150.00  188
 28  ω     16.00 183.00   0.50    0.80    --   93.40   8.00 -30.00  334
 29  ω    128.00 162.00   0.50    0.80    --   93.40  82.00-150.00   68
 30  ω     90.00 115.00   0.50    0.80    --   93.40  82.00-150.00   50
 31  ω     61.00  98.00   0.50    0.80    --   93.40 -82.00  30.00   74
 32  ω     66.00  92.00   0.50    0.80    --   93.40 -82.00 150.00   52
 33  ω     15.00 121.00   0.50    0.80    --   93.40 -82.00 -60.00  212
 34  ω     71.00 101.00   0.50    0.80    --   93.40 -82.00-120.00   60
 35  ω     56.00  83.00   0.50    0.80    --   93.40 -82.00 -30.00   54
 36  ω      4.00 116.00   0.50    0.80    --   93.40 -42.00  30.00  224
 37  ω     10.00  66.00   0.50    0.80    --   93.40 -59.00 120.00  112
 38  ω     62.00  95.00   0.50    0.80    --   93.40 -82.00  99.41   66
 39  ω     70.00  96.00   0.50    0.80    --   93.40 -82.00   0.00   52
 40  ω     59.00  84.00   0.50    0.80    --   93.40 -82.00  60.00   50
 41  ω     55.00  80.00   0.50    0.80    --   93.40 -82.00 120.00   50
 42  ω     10.00  35.00   0.50    0.80    --   93.40 -82.00  99.41   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0176763000
_diffrn_orient_matrix_UB_12      -0.1525710000
_diffrn_orient_matrix_UB_13      -0.0085489000
_diffrn_orient_matrix_UB_21      0.0368898000
_diffrn_orient_matrix_UB_22      0.0299488000
_diffrn_orient_matrix_UB_23      -0.0446547000
_diffrn_orient_matrix_UB_31      0.3077109000
_diffrn_orient_matrix_UB_32      0.0051269000
_diffrn_orient_matrix_UB_33      0.0058381000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            13803
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.505
_diffrn_reflns_theta_max         67.505
_diffrn_reflns_theta_min         2.630
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 776 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0571P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2410
_reflns_number_total             2934
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc01860k2.cif
_cod_data_source_block           exp_337
_cod_depositor_comments
'Adding full bibliography for 7241227--7241236.cif.'
_cod_database_code               7241236
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_oxdiff_digest_frames
;
0162219eb7280e164a9e4ea75fe341451f041882cb0
;
_diffrn_oxdiff_digest_hkl
;
01f6badeb7dfaefd7337108f545fff6674efa1
;
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C00A(H00A), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I),
 C00L(H00L), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00H(H00B,H00C,H00D), C00J(H00H,H00J,H00K), C00N(H00N,H00O,H00P)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.892
_oxdiff_exptl_absorpt_empirical_full_min 0.697
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 0.2125(2) 0.45639(10) 0.27896(3) 0.0519(3) Uani 1 1 d . . . . .
O002 O 0.7559(6) 0.6874(3) 0.37999(9) 0.0690(9) Uani 1 1 d . . . . .
N003 N 0.3131(6) 0.7182(3) 0.39271(9) 0.0485(8) Uani 1 1 d . . . . .
H003 H 0.153945 0.691742 0.386234 0.058 Uiso 1 1 calc R . . . .
O004 O -0.0936(6) 0.7078(3) 0.27847(10) 0.0739(10) Uani 1 1 d . . . . .
C005 C 0.5192(7) 0.6645(4) 0.37201(12) 0.0451(9) Uani 1 1 d . . . . .
C006 C 0.5544(7) 0.4365(4) 0.33728(10) 0.0426(9) Uani 1 1 d . . . . .
C007 C 0.4417(7) 0.5703(4) 0.33938(11) 0.0428(9) Uani 1 1 d . . . . .
C008 C 0.3303(8) 0.8138(4) 0.42407(11) 0.0453(9) Uani 1 1 d . . . . .
C009 C 0.2596(8) 0.5939(4) 0.30972(10) 0.0433(9) Uani 1 1 d . . . . .
C00A C 0.7471(8) 0.3743(4) 0.36188(10) 0.0476(9) Uani 1 1 d . . . . .
H00A H 0.819600 0.421663 0.383244 0.057 Uiso 1 1 calc R . . . .
C00B C 0.1117(8) 0.7186(4) 0.29798(12) 0.0498(10) Uani 1 1 d . . . . .
C00C C 0.4471(8) 0.3630(4) 0.30539(11) 0.0468(10) Uani 1 1 d . . . . .
C00D C 0.8295(8) 0.2437(4) 0.35455(12) 0.0535(10) Uani 1 1 d . . . . .
C00E C 0.5283(9) 0.2308(4) 0.29747(13) 0.0558(11) Uani 1 1 d . . . . .
H00E H 0.456058 0.182355 0.276298 0.067 Uiso 1 1 calc R . . . .
C00F C 0.7198(9) 0.1746(4) 0.32220(12) 0.0581(11) Uani 1 1 d . . . . .
H00F H 0.778120 0.087107 0.317094 0.070 Uiso 1 1 calc R . . . .
C00G C 0.1540(10) 0.8043(5) 0.45526(12) 0.0646(12) Uani 1 1 d . . . . .
H00G H 0.025802 0.735776 0.455717 0.077 Uiso 1 1 calc R . . . .
C00H C 1.0437(9) 0.1784(5) 0.38054(14) 0.0675(13) Uani 1 1 d . . . . .
H00B H 1.211792 0.176129 0.366417 0.101 Uiso 1 1 calc GR . . . .
H00C H 0.989847 0.087934 0.387062 0.101 Uiso 1 1 calc GR . . . .
H00D H 1.064789 0.229780 0.404562 0.101 Uiso 1 1 calc GR . . . .
C00I C 0.5152(9) 0.9169(5) 0.42367(14) 0.0653(13) Uani 1 1 d . . . . .
H00I H 0.634772 0.925981 0.402527 0.078 Uiso 1 1 calc R . . . .
C00J C 0.2337(11) 0.8538(4) 0.30733(14) 0.0711(13) Uani 1 1 d . . . . .
H00H H 0.188946 0.916693 0.286618 0.107 Uiso 1 1 calc GR . . . .
H00J H 0.425990 0.845072 0.309093 0.107 Uiso 1 1 calc GR . . . .
H00K H 0.164189 0.885996 0.332239 0.107 Uiso 1 1 calc GR . . . .
C00K C 0.3516(11) 0.9984(5) 0.48667(14) 0.0700(14) Uani 1 1 d . . . . .
C00L C 0.1666(11) 0.8964(6) 0.48601(13) 0.0770(15) Uani 1 1 d . . . . .
H00L H 0.045228 0.888680 0.506968 0.092 Uiso 1 1 calc R . . . .
C00M C 0.5216(10) 1.0071(5) 0.45501(15) 0.0750(15) Uani 1 1 d . . . . .
H00M H 0.647349 1.076630 0.454451 0.090 Uiso 1 1 calc R . . . .
C00N C 0.3675(15) 1.0944(6) 0.52164(16) 0.112(2) Uani 1 1 d . . . . .
H00N H 0.201782 1.091109 0.536330 0.168 Uiso 1 1 calc GR . . . .
H00O H 0.396981 1.184556 0.512108 0.168 Uiso 1 1 calc GR . . . .
H00P H 0.513960 1.068341 0.538656 0.168 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 S01 C00C 91.33(19) . . ?
C005 N003 C008 127.0(3) . . ?
O002 C005 N003 122.8(4) . . ?
O002 C005 C007 121.6(4) . . ?
N003 C005 C007 115.6(3) . . ?
C00A C006 C007 129.7(4) . . ?
C00C C006 C007 111.6(3) . . ?
C00C C006 C00A 118.8(4) . . ?
C006 C007 C005 120.8(3) . . ?
C009 C007 C005 126.9(4) . . ?
C009 C007 C006 112.3(3) . . ?
C00G C008 N003 118.9(4) . . ?
C00G C008 C00I 119.1(4) . . ?
C00I C008 N003 122.0(4) . . ?
C007 C009 S01 113.0(3) . . ?
C007 C009 C00B 131.4(3) . . ?
C00B C009 S01 115.4(3) . . ?
C00D C00A C006 120.5(4) . . ?
O004 C00B C009 118.8(4) . . ?
O004 C00B C00J 121.9(4) . . ?
C009 C00B C00J 119.0(3) . . ?
C006 C00C S01 111.8(3) . . ?
C00E C00C S01 126.7(3) . . ?
C00E C00C C006 121.6(4) . . ?
C00A C00D C00F 118.9(4) . . ?
C00A C00D C00H 120.3(4) . . ?
C00F C00D C00H 120.8(4) . . ?
C00F C00E C00C 117.5(4) . . ?
C00E C00F C00D 122.7(4) . . ?
C008 C00G C00L 119.9(5) . . ?
C008 C00I C00M 119.2(4) . . ?
C00L C00K C00N 120.8(5) . . ?
C00M C00K C00L 116.8(4) . . ?
C00M C00K C00N 122.4(5) . . ?
C00K C00L C00G 122.1(5) . . ?
C00K C00M C00I 122.8(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S01 C009 1.726(4) . ?
S01 C00C 1.732(4) . ?
O002 C005 1.226(4) . ?
N003 C005 1.347(5) . ?
N003 C008 1.419(5) . ?
O004 C00B 1.217(5) . ?
C005 C007 1.490(5) . ?
C006 C007 1.440(5) . ?
C006 C00A 1.406(5) . ?
C006 C00C 1.400(5) . ?
C007 C009 1.366(5) . ?
C008 C00G 1.369(6) . ?
C008 C00I 1.373(6) . ?
C009 C00B 1.490(5) . ?
C00A C00D 1.379(5) . ?
C00B C00J 1.502(6) . ?
C00C C00E 1.396(6) . ?
C00D C00F 1.395(6) . ?
C00D C00H 1.521(6) . ?
C00E C00F 1.379(6) . ?
C00G C00L 1.380(6) . ?
C00I C00M 1.381(6) . ?
C00K C00L 1.365(7) . ?
C00K C00M 1.360(7) . ?
C00K C00N 1.513(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341643
