Construction of Benzothiophene or Benzothiopheno[2,3-<i>e</i>]azepinedione Derivatives via Three-Component Domino or One-Pot Sequences.
Deng, Qingsong; Yu, Aimin; Zhou, Jie; Cao, Qin; Meng, Xiangtai; The Journal of organic chemistry 85 (2020) 12270–12283; doi:10.1021/acs.joc.0c01505

data_4038804
_publ_section_title
;
 Construction of Benzothiophene or
 Benzothiopheno[2,3-<i>e</i>]azepinedione Derivatives via Three-Component
 Domino or One-Pot Sequences.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12270
_journal_page_last               12283
_journal_paper_doi               10.1021/acs.joc.0c01505
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C24 H17 N O3 S'
_chemical_formula_sum            'C24 H17 N O3 S'
_chemical_formula_weight         399.44
_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             2019-02-27
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_cell_angle_alpha                99.201(2)
_cell_angle_beta                 111.404(2)
_cell_angle_gamma                102.937(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6034(2)
_cell_length_b                   10.0317(2)
_cell_length_c                   12.4075(2)
_cell_measurement_reflns_used    5510
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.7570
_cell_measurement_theta_min      3.9620
_cell_volume                     1045.48(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     20.00  56.00   0.50    0.05    --   43.80 -53.00 -39.00   72
  2  \w     78.00 133.00   0.50    0.09    --  111.75 -53.00 -39.00  110
  3  \w     77.00 103.00   0.50    0.09    --  111.75 -94.00 -90.00   52
  4  \w     96.00 121.00   0.50    0.09    --  111.75-125.00 -30.00   50
  5  \w     72.00 123.00   0.50    0.05    --   43.80-178.00  30.00  102
  6  \w     68.00 103.00   0.50    0.09    --  111.75 -94.00  90.00   70
  7  \w     92.00 133.00   0.50    0.09    --  111.75 -45.00  90.00   82
  8  \w     90.00 173.00   0.50    0.09    --  111.75  45.00  30.00  166
  9  \w    153.00 178.00   0.50    0.09    --  111.75 125.00  30.00   50
 10  \w     84.00 117.00   0.50    0.05    --   43.80  53.00 104.00   66
 11  \w     92.00 133.00   0.50    0.09    --  111.75 125.00  30.00   82
 12  \w     91.00 177.00   0.50    0.09    --  111.75  53.00 104.00  172
 13  \w     92.00 158.00   0.50    0.09    --  111.75 125.00 -90.00  132
 14  \w     94.00 157.00   0.50    0.09    --  111.75  45.00-180.00  126
 15  \w     89.00 125.00   0.50    0.09    --  111.75  30.00-120.00   72
 16  \w     41.00  72.00   0.50    0.09    --  111.75 -53.00 -39.00   62
 17  \w     40.00 135.00   0.50    0.09    --  111.75 -77.00 -30.00  190
 18  \w     56.00 118.00   0.50    0.09    --  111.75-125.00-180.00  124
 19  \w     38.00  69.00   0.50    0.09    --  111.75 -94.00 -90.00   62
 20  \w     59.00  85.00   0.50    0.09    --  111.75-125.00 -30.00   52
 21  \w    -30.00  14.00   0.50    0.05    --   43.80 -53.00 -39.00   88
 22  \w     23.00  55.00   0.50    0.05    --   43.80  53.00 104.00   64
 23  \w     -7.00  27.00   0.50    0.05    --  -43.80  53.00 104.00   68
 24  \w    -70.00 -28.00   0.50    0.05    --  -43.80 -53.00 -39.00   84
 25  \w    -88.00 -63.00   0.50    0.09    --  -90.25  53.00 104.00   50
 26  \w    -85.00 -22.00   0.50    0.09    --  -90.25 125.00 120.00  126
 27  \w   -112.00 -14.00   0.50    0.09    --  -90.25  45.00 -60.00  196
 28  \w    -60.00 -22.00   0.50    0.09    --  -90.25 125.00-180.00   76
 29  \w    -95.00 -70.00   0.50    0.09    --  -90.25 125.00-180.00   50
 30  \w   -161.00-136.00   0.50    0.09    --  -90.25 -53.00 -39.00   50
 31  \w   -120.00 -72.00   0.50    0.09    --  -90.25 -53.00 -39.00   96
 32  \w   -117.00 -79.00   0.50    0.05    --  -43.80 -53.00 -39.00   76
 33  \w   -118.00 -88.00   0.50    0.09    --  -90.25 -94.00-180.00   60
 34  \w    -94.00 -39.00   0.50    0.05    --  -43.80-178.00 -30.00  110
 35  \w     63.00 101.00   0.50    0.05    --   43.80 178.00-120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0945250000
_diffrn_orient_matrix_UB_12      0.0221448000
_diffrn_orient_matrix_UB_13      0.0747784000
_diffrn_orient_matrix_UB_21      0.0933295000
_diffrn_orient_matrix_UB_22      0.1591850000
_diffrn_orient_matrix_UB_23      0.0473789000
_diffrn_orient_matrix_UB_31      -0.1230199000
_diffrn_orient_matrix_UB_32      0.0298707000
_diffrn_orient_matrix_UB_33      -0.1063287000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9794
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         3.970
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0472P)^2^+0.6647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3353
_reflns_number_total             3723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01505_si_002.cif
_cod_data_source_block           hubu-zmh-wy-2-20190227
_cod_depositor_comments
'Adding full bibliography for 4038801--4038807.cif.'
_cod_database_code               4038804
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'c h o n'
_diffrn_oxdiff_ac3_digest_frames
;
01a4ad310251bf4b2808aa068ddbf79444000725762
;
_diffrn_oxdiff_ac3_digest_hkl
;
01fa65913f7e5e31a967ced14008e6ef8dbe03
;
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C4(H4), C5(H5), C9(H9), C10(H10), C24(H24), C12(H12),
 C11(H11), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C23(H23A,H23B,H23C)
;
_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 2.162
_oxdiff_exptl_absorpt_empirical_full_min 0.465