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_4038802
_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         'C23 H19 N O3 S'
_chemical_formula_sum            'C23 H19 N O3 S'
_chemical_formula_weight         389.45
_chemical_name_systematic        11111
_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     iterative
_audit_creation_date             2019-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.2291(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.59534(17)
_cell_length_b                   10.30762(9)
_cell_length_c                   22.2729(2)
_cell_measurement_reflns_used    10073
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.3310
_cell_measurement_theta_min      2.0560
_cell_volume                     3878.58(6)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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    -49.00  23.00   0.50    1.50    --   40.80 -77.00-180.00  144
  2  \w     35.00  72.00   0.50    1.50    --   40.80 -32.00-150.00   74
  3  \w    -45.00 -20.00   0.50    1.50    --   40.80 -77.00 -60.00   50
  4  \w     62.00 123.00   0.50    1.50    --   40.80  77.00 -30.00  122
  5  \w    -40.00  27.00   0.50    1.50    --   40.80 -77.00   0.00  134
  6  \w    -48.00  -5.00   0.50    1.50    --   40.80 -82.00 -30.00   86
  7  \w    -42.00  -2.00   0.50    1.50    --   40.80 -32.00-150.00   80
  8  \w     20.00  57.00   0.50    1.50    --   40.80 -77.00 -60.00   74
  9  \w     17.00  68.00   0.50    1.50    --   40.80 -82.00 -30.00  102
 10  \w     15.00  67.00   0.50    1.50    --   40.80 -82.00  60.00  104
 11  \w     22.00 127.00   0.50    1.50    --   40.80  32.00  90.00  210
 12  \w      9.00  66.00   0.50    1.50    --   40.80 -82.00  90.00  114
 13  \w    -22.00   4.00   0.50    1.50    --   40.80 -82.00  90.00   52
 14  \w     28.00  65.00   0.50    1.50    --   40.80 -77.00-180.00   74
 15  \w     23.00  68.00   0.50    1.50    --   40.80 -82.00-120.00   90
 16  \w     22.00  47.00   0.50    1.50    --   40.80 -82.00-150.00   50
 17  \w    -30.00  13.00   0.50    1.50    --   40.80 -65.00-150.00   86
 18  \w     38.00  64.00   0.50    1.50    --   40.80 -65.00-150.00   52
 19  \w     95.00 183.00   0.50    4.00    --   93.40  68.00-150.00  176
 20  \w     79.00 157.00   0.50    4.00    --   93.40  33.00 120.00  156
 21  \w     60.00 181.00   0.50    4.00    --   93.40  50.00   0.00  242
 22  \w      4.00  90.00   0.50    4.00    --   93.40 -82.00 -60.00  172
 23  \w    115.00 178.00   0.50    4.00    --   93.40  33.00 -60.00  126
 24  \w     71.00 110.00   0.50    4.00    --   93.40 -82.00   0.00   78
 25  \w     37.00  70.00   0.50    4.00    --   93.40 -82.00-150.00   66
 26  \w     76.00 101.00   0.50    4.00    --   93.40 -82.00-150.00   50
 27  \w     55.00 167.00   0.50    4.00    --   93.40  33.00  60.00  224
 28  \w     65.00 100.00   0.50    4.00    --   93.40  33.00 -60.00   70
 29  \w     54.00  80.00   0.50    4.00    --   93.40 -82.00-120.00   52
 30  \w     50.00  94.00   0.50    4.00    --   93.40 -82.00  90.00   88
 31  \w     45.00  91.00   0.50    4.00    --   93.40 -82.00 -30.00   92
 32  \w      4.00  68.00   0.50    4.00    --   93.40 -82.00  60.00  128
 33  \w     26.00  66.00   0.50    4.00    --   93.40 -82.00   0.00   80
 34  \w    158.00 183.00   0.50    4.00    --   93.40  59.00 -60.00   50
 35  \w     67.00 117.00   0.50    4.00    --   93.40  59.00 -60.00  100
 36  \w     79.00 105.00   0.50    4.00    --   93.40 -82.00  30.00   52
 37  \w     26.00  66.00   0.50    4.00    --   93.40 -82.00  30.00   80
 38  \w      4.00  91.50   0.50    4.00    --   93.40 -82.00 150.00  175
;
_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      0.0881273000
_diffrn_orient_matrix_UB_12      -0.0259283000
_diffrn_orient_matrix_UB_13      0.0063500000
_diffrn_orient_matrix_UB_21      -0.0233643000
_diffrn_orient_matrix_UB_22      -0.0916348000
_diffrn_orient_matrix_UB_23      -0.0568146000
_diffrn_orient_matrix_UB_31      0.0012178000
_diffrn_orient_matrix_UB_32      0.1152250000
_diffrn_orient_matrix_UB_33      -0.0438125000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14227
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.481
_diffrn_reflns_theta_max         67.481
_diffrn_reflns_theta_min         4.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51060
_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 yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0520P)^2^+2.3398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3261
_reflns_number_total             3439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01505_si_002.cif
_cod_data_source_block           exp_35
_cod_depositor_comments
'Adding full bibliography for 4038801--4038807.cif.'
_cod_original_cell_volume        3878.58(7)
_cod_database_code               4038802
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.877
_diffrn_oxdiff_digest_frames
;
01cded20d38ac2729f4621e2159c668506000267692
;
_diffrn_oxdiff_digest_hkl
;
0106816906912aeb5d1f9bc3c9f63271d87827
;
_reflns_odcompleteness_completeness 98.62
_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 N(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:
 C00A(H00A)
2.b Aromatic/amide H refined with riding coordinates:
 N004(H004), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00R(H00B,H00C,H00E)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              15581
_shelx_hkl_checksum              85502
_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 1.878
_oxdiff_exptl_absorpt_empirical_full_min 0.776