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_7241233
_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         'C21 H19 N O4 S'
_chemical_formula_sum            'C21 H19 N O4 S'
_chemical_formula_weight         381.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-08-06 deposited with the CCDC.	2020-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.5250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.9374(2)
_cell_length_b                   18.7941(2)
_cell_length_c                   16.6525(2)
_cell_measurement_reflns_used    6919
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0250
_cell_measurement_theta_min      2.6660
_cell_volume                     3718.68(9)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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     40.00  67.00   0.50    0.50    --   40.90 -82.00 120.00   54
  2  \w    -26.00  64.00   0.50    0.50    --   40.90 -65.00 -30.00  180
  3  \w     20.00  90.00   0.50    0.50    --   40.90  82.00-120.00  140
  4  \w    -13.00  46.00   0.50    0.50    --   40.90 -82.00 -60.00  118
  5  \w    -43.00 -18.00   0.50    0.50    --   40.90 -82.00 120.00   50
  6  \w     17.00  52.00   0.50    0.50    --   40.90  43.00  60.00   70
  7  \w    -43.00  -2.00   0.50    0.50    --   40.90 -65.00-120.00   82
  8  \w    -49.00  17.00   0.50    0.50    --   40.90 -82.00-180.00  132
  9  \w     63.00 118.00   0.50    0.50    --   40.90  43.00  60.00  110
 10  \w    -43.00  27.00   0.50    0.50    --   40.90 -82.00  90.00  140
 11  \w     14.00 111.00   0.50    0.50    --   40.90  82.00-180.00  194
 12  \w      5.00  33.00   0.50    0.50    --   40.90 -82.00 120.00   56
 13  \w     39.00  65.00   0.50    0.50    --   40.90 -82.00 -30.00   52
 14  \w     35.00  64.00   0.50    0.50    --   40.90 -82.00  90.00   58
 15  \w    -35.00 -10.00   0.50    0.50    --   40.90 -82.00 -30.00   50
 16  \w     41.00  68.00   0.50    0.50    --   40.90 -82.00-180.00   54
 17  \w     70.00  96.00   0.50    0.50    --   40.90  65.00 120.00   52
 18  \w     18.00  46.00   0.50    0.50    --   40.90  65.00 120.00   56
 19  \w    103.00 129.00   0.50    0.50    --   40.90  82.00-120.00   52
 20  \w     10.00 108.00   0.50    0.50    --   93.40 -82.00-150.00  196
 21  \w    111.00 177.00   0.50    0.50    --   93.40  42.00 120.00  132
 22  \w     20.00  90.00   0.50    0.50    --   93.40 -82.00-180.00  140
 23  \w     58.00  95.00   0.50    0.50    --   93.40  42.00 120.00   74
 24  \w     97.00 124.00   0.50    0.50    --   93.40 -42.00-120.00   54
 25  \w      4.00  37.00   0.50    0.50    --   93.40 -42.00  30.00   66
 26  \w     59.00  85.00   0.50    0.50    --   93.40 -82.00  30.00   52
 27  \w     97.00 122.00   0.50    0.50    --   93.40  50.00  30.00   50
 28  \w      6.00  81.00   0.50    0.50    --   93.40 -82.00 -60.00  150
 29  \w     28.00  84.00   0.50    0.50    --   93.40 -33.00 150.00  112
 30  \w      9.00  37.00   0.50    0.50    --   93.40 -82.00 120.00   56
 31  \w      7.00  60.00   0.50    0.50    --   93.40 -68.00   0.00  106
 32  \w     21.00  92.00   0.50    0.50    --   93.40 -82.00 150.00  142
 33  \w     20.00  68.00   0.50    0.50    --   93.40 -42.00-120.00   96
 34  \w     53.00  98.00   0.50    0.50    --   93.40 -82.00 -30.00   90
 35  \w    121.00 181.00   0.50    0.50    --   93.40  68.00  90.00  120
 36  \w     69.00  95.00   0.50    0.50    --   93.40  68.00  90.00   52
 37  \w     50.00  92.00   0.50    0.50    --   93.40 -82.00  90.00   84
 38  \w     45.00  97.00   0.50    0.50    --   93.40 -82.00   0.00  104
 39  \w      8.00  38.00   0.50    0.50    --   93.40 -82.00  90.00   60
 40  \w     44.00  90.00   0.50    0.50    --   93.40 -82.00 120.00   92
 41  \w      4.00 104.00   0.50    0.50    --   93.40 -82.00 -90.00  200
 42  \w     40.00  95.00   0.50    0.50    --   93.40 -82.00-120.00  110
 43  \w     57.00 124.00   0.50    0.50    --   93.40 -42.00  30.00  134
 44  \w      5.00  30.00   0.50    0.50    --   93.40 -82.00  30.00   50
 45  \w     21.00 183.00   0.50    0.50    --   93.40  -8.00  90.00  324
 46  \w     11.00 103.00   0.50    0.50    --   93.40 -82.00  38.60  184
;
_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      -0.0811313000
_diffrn_orient_matrix_UB_12      0.0294355000
_diffrn_orient_matrix_UB_13      -0.0697068000
_diffrn_orient_matrix_UB_21      -0.1011879000
_diffrn_orient_matrix_UB_22      -0.0223806000
_diffrn_orient_matrix_UB_23      0.0450687000
_diffrn_orient_matrix_UB_31      0.0015933000
_diffrn_orient_matrix_UB_32      0.0731147000
_diffrn_orient_matrix_UB_33      0.0418285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17157
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.528
_diffrn_reflns_theta_max         67.528
_diffrn_reflns_theta_min         4.402
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51884
_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    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_refine_diff_density_max         1.028
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00040(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.297
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0567
_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^)+(0.1054P)^2^+3.9562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.1827
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2892
_reflns_number_total             3352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc01860k2.cif
_cod_data_source_block           zj26
_cod_depositor_comments
'Adding full bibliography for 7241227--7241236.cif.'
_cod_database_code               7241233
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.97
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C22, C23
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
3. Uiso/Uaniso restraints and constraints
C23 \\sim C22 \\sim O21: within 2.7A with sigma of 0.004 and sigma for terminal
atoms of 0.008 within 2.7A
4.a Ternary CH refined with riding coordinates:
 C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C19(H19), C6(H6), C7(H7), C14(H14), C18(H18), C16(H16), C17(H17),
 C15(H15)
4.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C23(H23A,H23B,H23C)
4.e Idealised tetrahedral OH refined as rotating group:
 O26(H26)
;
_shelx_res_checksum              21825
_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 2.053
_oxdiff_exptl_absorpt_empirical_full_min 0.709