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_7241227
_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         'C22 H21 N O4 S'
_chemical_formula_sum            'C22 H21 N O4 S'
_chemical_formula_weight         395.46
_chemical_name_systematic        111
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-28 deposited with the CCDC.	2020-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.9250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.75170(10)
_cell_length_b                   11.70550(10)
_cell_length_c                   19.7505(2)
_cell_measurement_reflns_used    10458
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3090
_cell_measurement_theta_min      4.4110
_cell_volume                     1979.64(4)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_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     38.00 107.00   0.50    1.50    --   40.90  77.00  90.00  138
  2  \w     25.00  51.00   0.50    1.50    --   40.90 -77.00   0.00   52
  3  \w    -36.00  -8.00   0.50    1.50    --   40.90 -82.00 -90.00   56
  4  \w    -30.00  -4.00   0.50    1.50    --   40.90 -82.00-150.00   52
  5  \w     10.00  90.00   0.50    1.50    --   40.90  54.00 -30.00  160
  6  \w      8.00  68.00   0.50    1.50    --   40.90 -82.00 150.00  120
  7  \w     42.00  67.00   0.50    1.50    --   40.90 -82.00   0.00   50
  8  \w     54.00 114.00   0.50    1.50    --   40.90  43.00 120.00  120
  9  \w     95.00 127.00   0.50    1.50    --   40.90  54.00 -30.00   64
 10  \w      2.00  60.00   0.50    1.50    --   40.90 -82.00-150.00  116
 11  \w     21.00 130.00   0.50    1.50    --   40.90  77.00   0.00  218
 12  \w     31.00  57.00   0.50    1.50    --   40.90  77.00 150.00   52
 13  \w     80.00 117.00   0.50    1.50    --   40.90  77.00 150.00   74
 14  \w    -26.00  66.00   0.50    1.50    --   40.90 -77.00-120.00  184
 15  \w    -16.00  66.00   0.50    1.50    --   40.90 -82.00  60.00  164
 16  \w     42.00  67.00   0.50    1.50    --   40.90 -82.00  90.00   50
 17  \w     18.00  68.00   0.50    1.50    --   40.90 -82.00 -90.00  100
 18  \w    -14.00  48.00   0.50    1.50    --   40.90 -65.00  60.00  124
 19  \w     60.00 183.00   0.50    5.00    --   93.40  50.00  60.00  246
 20  \w    142.00 168.00   0.50    5.00    --   93.40  50.00  90.00   52
 21  \w      4.00  66.00   0.50    5.00    --   93.40 -77.00 150.00  124
 22  \w     49.00  93.00   0.50    5.00    --   93.40 -82.00   0.00   88
 23  \w     97.00 147.00   0.50    5.00    --   93.40  68.00 -90.00  100
 24  \w     60.00 123.00   0.50    5.00    --   93.40  50.00  90.00  126
 25  \w     35.00  61.00   0.50    5.00    --   93.40 -82.00 -60.00   52
 26  \w     61.00 110.00   0.50    5.00    --   93.40 -82.00-180.00   98
 27  \w     13.00  58.00   0.50    5.00    --   93.40 -82.00-180.00   90
 28  \w     71.00  96.00   0.50    5.00    --   93.40 -82.00 -30.00   50
 29  \w      4.00  97.00   0.50    5.00    --   93.40 -82.00  30.00  186
 30  \w     69.00 183.00   0.50    5.00    --   93.40  68.00   0.00  228
 31  \w      4.00 103.00   0.50    5.00    --   93.40 -82.00 120.00  198
 32  \w     24.00  96.00   0.50    5.00    --   93.40 -82.00  90.00  144
 33  \w     50.00 120.00   0.50    5.00    --   93.40 -82.00-120.00  140
 34  \w     16.00  92.00   0.50    5.00    --   93.40 -82.00-150.00  152
 35  \w     49.00  94.00   0.50    5.00    --   93.40 -82.00  60.00   90
 36  \w     69.00 151.00   0.50    5.00    --   93.40  68.00 -30.00  164
 37  \w     68.00  93.00   0.50    5.00    --   93.40 -82.00 -60.00   50
 38  \w     21.00 112.00   0.50    5.00    --   93.40 -82.00 -90.00  182
 39  \w     85.00 142.00   0.50    5.00    --   93.40  77.00 -60.00  114
 40  \w    112.00 169.00   0.50    5.00    --   93.40  42.00  30.00  114
;
_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      -0.1618697000
_diffrn_orient_matrix_UB_12      0.0489085000
_diffrn_orient_matrix_UB_13      -0.0326450000
_diffrn_orient_matrix_UB_21      0.0744256000
_diffrn_orient_matrix_UB_22      0.0739712000
_diffrn_orient_matrix_UB_23      -0.0490723000
_diffrn_orient_matrix_UB_31      -0.0248112000
_diffrn_orient_matrix_UB_32      -0.0972797000
_diffrn_orient_matrix_UB_33      -0.0536846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16915
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.542
_diffrn_reflns_theta_max         67.542
_diffrn_reflns_theta_min         4.416
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84105
_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_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.3594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3024
_reflns_number_total             3476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc01860k2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7241227--7241236.cif.'
_cod_database_code               7241227
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.877
_diffrn_oxdiff_digest_frames
;
015b2439112ae4d0188707c7903fb8e0f704682be9d
;
_diffrn_oxdiff_digest_hkl
;
010d85b64879b4b835637c581b024c3fd68499
;
_reflns_odcompleteness_completeness 98.00
_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.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C20(H20), C19(H19), C6(H6), C15(H15), C7(H7), C18(H18), C17(H17),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O27(H27)
;
_shelx_res_checksum              88198
_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 3.129
_oxdiff_exptl_absorpt_empirical_full_min 0.617