Construction of benzothiophene fused pyrrolidone in water via a catalyst-free process and a mechanism study
Shen, Jinhui; Yu, Aimin; Zhang, Lei; Meng, Xiangtai; Green Chemistry 22 (2020) 6798–6803; doi:10.1039/D0GC01860K

data_7241236
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w     19.00  45.00   0.50    0.80    --   40.90 -43.00  30.00   52
  2  \w    -49.00  12.00   0.50    0.80    --   40.90 -43.00-180.00  122
  3  \w     18.00  72.00   0.50    0.80    --   40.90 -43.00-180.00  108
  4  \w    -49.00   1.00   0.50    0.80    --   40.90 -82.00 -60.00  100
  5  \w    -49.00  13.00   0.50    0.80    --   40.90 -43.00  30.00  124
  6  \w     25.00  67.00   0.50    0.80    --   40.90 -82.00  90.00   84
  7  \w     -1.00  66.00   0.50    0.80    --   40.90 -82.00  30.00  134
  8  \w     30.00  66.00   0.50    0.80    --   40.90 -82.00 -30.00   72
  9  \w    -30.00   2.00   0.50    0.80    --   40.90 -82.00  90.00   64
 10  \w     14.00  48.00   0.50    0.80    --   40.90 -82.00 -60.00   68
 11  \w    -27.00   6.00   0.50    0.80    --   40.90 -82.00 -30.00   66
 12  \w     50.00  75.00   0.50    0.80    --   40.90 -43.00  30.00   50
 13  \w    -33.00  -7.00   0.50    0.80    --   40.90 -65.00-180.00   52
 14  \w      4.00  52.00   0.50    0.80    --   40.90 -65.00-180.00   96
 15  \w    -49.00  35.00   0.50    0.80    --   40.90 -77.00 150.00  168
 16  \w     27.00  68.00   0.50    0.80    --   40.90 -82.00-180.00   82
 17  \w     33.00  64.00   0.50    0.80    --   40.90  54.00  30.00   62
 18  \w    -21.00  14.00   0.50    0.80    --   40.90 -65.00 -30.00   70
 19  \w      6.00 122.00   0.50    0.80    --   93.40 -50.00 -60.00  232
 20  \w     18.00  92.00   0.50    0.80    --   93.40 -33.00 -60.00  148
 21  \w    132.00 181.00   0.50    0.80    --   93.40  82.00-120.00   98
 22  \w     13.00  64.00   0.50    0.80    --   93.40 -77.00 -90.00  102
 23  \w     66.00  95.00   0.50    0.80    --   93.40  82.00-120.00   58
 24  \w     16.00  94.00   0.50    0.80    --   93.40 -82.00-180.00  156
 25  \w    147.00 183.00   0.50    0.80    --   93.40  59.00   0.00   72
 26  \w    111.00 137.00   0.50    0.80    --   93.40  59.00   0.00   52
 27  \w      4.00  98.00   0.50    0.80    --   93.40 -82.00-150.00  188
 28  \w     16.00 183.00   0.50    0.80    --   93.40   8.00 -30.00  334
 29  \w    128.00 162.00   0.50    0.80    --   93.40  82.00-150.00   68
 30  \w     90.00 115.00   0.50    0.80    --   93.40  82.00-150.00   50
 31  \w     61.00  98.00   0.50    0.80    --   93.40 -82.00  30.00   74
 32  \w     66.00  92.00   0.50    0.80    --   93.40 -82.00 150.00   52
 33  \w     15.00 121.00   0.50    0.80    --   93.40 -82.00 -60.00  212
 34  \w     71.00 101.00   0.50    0.80    --   93.40 -82.00-120.00   60
 35  \w     56.00  83.00   0.50    0.80    --   93.40 -82.00 -30.00   54
 36  \w      4.00 116.00   0.50    0.80    --   93.40 -42.00  30.00  224
 37  \w     10.00  66.00   0.50    0.80    --   93.40 -59.00 120.00  112
 38  \w     62.00  95.00   0.50    0.80    --   93.40 -82.00  99.41   66
 39  \w     70.00  96.00   0.50    0.80    --   93.40 -82.00   0.00   52
 40  \w     59.00  84.00   0.50    0.80    --   93.40 -82.00  60.00   50
 41  \w     55.00  80.00   0.50    0.80    --   93.40 -82.00 120.00   50
 42  \w     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       '\w 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/[\s^2^(Fo^2^)+(0.0571P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_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)
;
_shelx_res_checksum              72462
_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