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_4038807
_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         'C22 H21 N O2 S, C0.5 H Cl'
_chemical_formula_sum            'C22.5 H22 Cl N O2 S'
_chemical_formula_weight         405.92
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.621(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.805(4)
_cell_length_b                   10.095(2)
_cell_length_c                   15.272(3)
_cell_measurement_reflns_used    1260
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.1220
_cell_measurement_theta_min      2.6410
_cell_volume                     4258.1(13)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -63.00 119.00   1.00    7.61    --   30.00  54.00-120.00  182
  2  \w     37.00  62.00   1.00    7.61    --   30.00  54.00   0.00   25
  3  \w      6.00  42.00   1.00    7.61    --   30.00  54.00 150.00   36
;
_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      0.0047704000
_diffrn_orient_matrix_UB_12      0.0056710000
_diffrn_orient_matrix_UB_13      0.0464746000
_diffrn_orient_matrix_UB_21      0.0252432000
_diffrn_orient_matrix_UB_22      0.0019004000
_diffrn_orient_matrix_UB_23      -0.0034672000
_diffrn_orient_matrix_UB_31      -0.0011796000
_diffrn_orient_matrix_UB_32      0.0699078000
_diffrn_orient_matrix_UB_33      -0.0038029000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.1258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7764
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.578
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49070
_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    1.266
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1704
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1701
_refine_ls_R_factor_gt           0.0735
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.2584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1658
_reflns_number_total             3753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01505_si_003.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 4038801--4038807.cif.'
_cod_original_formula_sum        'C22.50 H22 Cl N O2 S'
_cod_database_code               4038807
_reflns_odcompleteness_completeness 99.87
_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. Rigid bond restraints
 C007, C00G
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Fixed Sof: Cl2(0.5) Cl3(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C00K(H00J,H00K), C00M(H00M,H00N), C00O(H00P,H00Q), C00Q(H00R,H00S), C00R(H00T,
 H00U)
4.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00G(H00G), C00H(H00H), C00I(H00I),
 C00L(H00L), C00N(H00O)
4.c Idealised Me refined as rotating group:
 C00J(H00D,H00E,H00F)
;
_shelx_res_checksum              59721
_shelx_hkl_checksum              9582
_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 1.757
_oxdiff_exptl_absorpt_empirical_full_min 0.354