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_7241234
_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 H23 N O4 S'
_chemical_formula_sum            'C19 H23 N O4 S'
_chemical_formula_weight         361.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-01
_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                108.185(11)
_cell_angle_beta                 106.055(11)
_cell_angle_gamma                109.685(12)
_cell_formula_units_Z            2
_cell_length_a                   9.0842(12)
_cell_length_b                   11.1680(14)
_cell_length_c                   11.3556(13)
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7300
_cell_measurement_theta_min      2.7470
_cell_volume                     932.0(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.870
_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      3.00 106.00   1.00    1.00    --   30.00  54.00 150.00  103
  2  \w     88.00 114.00   1.00    1.00    --   30.00  54.00  30.00   26
  3  \w    -73.00 111.00   1.00    1.00    --   30.00  54.00-120.00  184
  4  \w    -68.00 -34.00   1.00    1.00    --   30.00  54.00  30.00   34
;
_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      0.0011253000
_diffrn_orient_matrix_UB_12      0.0389641000
_diffrn_orient_matrix_UB_13      -0.0388269000
_diffrn_orient_matrix_UB_21      0.0589956000
_diffrn_orient_matrix_UB_22      0.0640079000
_diffrn_orient_matrix_UB_23      0.0606651000
_diffrn_orient_matrix_UB_31      0.0701859000
_diffrn_orient_matrix_UB_32      -0.0087445000
_diffrn_orient_matrix_UB_33      -0.0098454000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8158
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.805
_diffrn_reflns_theta_min         2.569
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73075
_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    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         6010
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0743
_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^)+(0.1242P)^2^+0.1997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2022
_refine_ls_wR_factor_ref         0.2594
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3180
_reflns_number_total             6010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc01860k2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7241227--7241236.cif.'
_cod_original_cell_volume        932.0(2)
_cod_database_code               7241234
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.74
_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, All O(H) groups
2. Rigid bond restraints
 C00H, C00M
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C00D(H00D)
3.b Secondary CH2 refined with riding coordinates:
 C00H(H00B,H00C), C00I(H00F,H00G), C00M(H00M,H00N), C00P(H00U,H00V)
3.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00J(H00J), C00K(H00K)
3.d Idealised Me refined as rotating group:
 C00L(H00H,H00I,H00L), C00N(H00O,H00P,H00Q), C00O(H00R,H00S,H00T)
3.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              47272
_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 1.656
_oxdiff_exptl_absorpt_empirical_full_min 0.608