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_7241232
_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 H19 N O3 S'
_chemical_formula_sum            'C22 H19 N O3 S'
_chemical_formula_weight         377.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-08
_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                 99.105(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0121(17)
_cell_length_b                   9.9422(14)
_cell_length_c                   15.9636(19)
_cell_measurement_reflns_used    1365
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3030
_cell_measurement_theta_min      2.9290
_cell_volume                     1882.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -74.00 110.00   1.00   20.00    --   30.00  54.00-150.00  184
  2  \w     84.00 117.00   1.00   20.00    --   30.00  54.00 120.00   33
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0071245000
_diffrn_orient_matrix_UB_12      -0.0200361000
_diffrn_orient_matrix_UB_13      0.0414347000
_diffrn_orient_matrix_UB_21      -0.0585673000
_diffrn_orient_matrix_UB_22      0.0138876000
_diffrn_orient_matrix_UB_23      -0.0098539000
_diffrn_orient_matrix_UB_31      -0.0099800000
_diffrn_orient_matrix_UB_32      -0.0670242000
_diffrn_orient_matrix_UB_33      -0.0144927000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.1224
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6254
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.004
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_min         3.322
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0321P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1624
_reflns_number_total             3307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc01860k2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7241227--7241236.cif.'
_cod_database_code               7241232
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00Q(H00L,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K),
 C00N(H00N), C00O(H00O), C00P(H00P)
2.c Idealised Me refined as rotating group:
 C00M(H00C,H00F,H00H), C00R(H00Q,H00R,H00S)
;
_shelx_res_checksum              17727
_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 1.791
_oxdiff_exptl_absorpt_empirical_full_min 0.407