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_4038801
_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         'C21 H20 Br N O2 S'
_chemical_formula_sum            'C21 H20 Br N O2 S'
_chemical_formula_weight         430.35
_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     direct
_audit_creation_date             2018-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.930(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6616(2)
_cell_length_b                   9.18547(12)
_cell_length_c                   17.0339(3)
_cell_measurement_reflns_used    7829
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      78.8530
_cell_measurement_theta_min      3.5660
_cell_volume                     1968.65(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (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_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_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     25.00  89.00   0.50    0.50    --    0.00  57.00 -30.00  128
  2  \w    -43.00 -16.00   0.50    0.50    --    0.00 -57.00 -30.00   54
  3  \w    -69.00  30.00   0.50    0.50    --    0.00 -37.00-150.00  198
  4  \w    -85.00 -56.00   0.50    0.50    --    0.00 -57.00 -30.00   58
  5  \w     17.00  42.00   0.50    1.00    --  106.20 -30.00   0.00   50
  6  \w     84.00 110.00   0.50    1.00    --  106.20  82.00   0.00   52
  7  \w    118.00 196.00   0.50    1.00    --  106.20  77.00 -60.00  156
  8  \w     19.00  44.00   0.50    1.00    --  106.20 -61.00 150.00   50
  9  \w     17.00 142.00   0.50    1.00    --  106.20 -82.00 -30.00  250
 10  \w     82.00 136.00   0.50    1.00    --  106.20 -61.00 150.00  108
 11  \w     78.00 108.00   0.50    1.00    --  106.20  61.00 -60.00   60
 12  \w     81.00 138.00   0.50    1.00    --  106.20 -30.00   0.00  114
 13  \w     98.00 123.00   0.50    1.00    --  106.20  45.00-150.00   50
 14  \w    143.00 169.00   0.50    1.00    --  106.20  82.00   0.00   52
 15  \w     48.00 136.00   0.50    1.00    --  106.20 -77.00 150.00  176
 16  \w     32.00 191.00   0.50    1.00    --  106.20   0.00  90.00  318
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0674687000
_diffrn_orient_matrix_UB_12      0.1191183000
_diffrn_orient_matrix_UB_13      -0.0606242000
_diffrn_orient_matrix_UB_21      0.0107705000
_diffrn_orient_matrix_UB_22      0.0957822000
_diffrn_orient_matrix_UB_23      0.0771704000
_diffrn_orient_matrix_UB_31      0.1016135000
_diffrn_orient_matrix_UB_32      0.0691571000
_diffrn_orient_matrix_UB_33      -0.0023525000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13021
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.429
_diffrn_reflns_theta_min         3.513
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.952
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_refine_diff_density_max         0.670
_refine_diff_density_min         -1.211
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.265
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.265
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3815
_reflns_number_total             4187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01505_si_002.cif
_cod_data_source_block           zgt181019
_cod_depositor_comments
'Adding full bibliography for 4038801--4038807.cif.'
_cod_original_cell_volume        1968.64(6)
_cod_database_code               4038801
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00O(H00J,H00N), C00P(H00O,H00P)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H), C00K(H00K),
 C00L(H00L), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C00N(H00D,H00F,H00I), C00Q(H00Q,H00R,H00S)
;
_shelx_res_checksum              42952
_shelx_hkl_checksum              66367
_shelx_shelxl_version_number     2014/7
_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 2.377
_oxdiff_exptl_absorpt_empirical_full_min 0.668