Catalyst-controlled switchable [4 + 1], [4 + 3] and [3 + 2] domino reactions of azadienes and MBH carbonates: diverse synthesis of benzothiophene fused derivatives.
Zeng, Wenlei; Yu, Aimin; Meng, Xiangtai; Organic & biomolecular chemistry 19 (2021) 8783–8788; doi:10.1039/d1ob01702k

data_7158313
_publ_section_title
;
 Catalyst-controlled switchable [4 + 1], [4 + 3] and [3 + 2] domino
 reactions of azadienes and MBH carbonates: diverse synthesis of
 benzothiophene fused derivatives.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8783
_journal_page_last               8788
_journal_paper_doi               10.1039/d1ob01702k
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C36 H29 Cl N2 O5 S2'
_chemical_formula_sum            'C36 H29 Cl N2 O5 S2'
_chemical_formula_weight         669.18
_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     iterative
_audit_creation_date             2021-06-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-27 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.556(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0158(8)
_cell_length_b                   10.2669(3)
_cell_length_c                   18.2254(6)
_cell_measurement_reflns_used    7329
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.7600
_cell_measurement_theta_min      2.2030
_cell_volume                     3728.0(2)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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     41.00  66.00   0.50    0.50    --   40.90 -77.00  90.00   50
  2  \w     99.00 125.00   0.50    0.50    --   40.90  77.00-180.00   52
  3  \w     16.00  84.00   0.50    0.50    --   40.90  65.00 120.00  136
  4  \w    -48.00  -9.00   0.50    0.50    --   40.90 -82.00 -60.00   78
  5  \w    -42.00  64.00   0.50    0.50    --   40.90 -82.00-150.00  212
  6  \w    -49.00  56.00   0.50    0.50    --   40.90 -11.00   0.00  210
  7  \w    -43.00  14.00   0.50    0.50    --   40.90 -82.00 -16.42  114
  8  \w     18.00  70.00   0.50    0.50    --   40.90 -54.00-150.00  104
  9  \w     -4.00  64.00   0.50    0.50    --   40.90 -82.00 -90.00  136
 10  \w     14.00  66.00   0.50    0.50    --   40.90 -82.00 -60.00  104
 11  \w     10.00  68.00   0.50    0.50    --   40.90 -82.00 150.00  116
 12  \w      7.00  68.00   0.50    0.50    --   40.90 -82.00  60.00  122
 13  \w    -49.00  11.00   0.50    0.50    --   40.90 -77.00  90.00  120
 14  \w    -43.00 -18.00   0.50    0.50    --   40.90 -82.00 150.00   50
 15  \w     80.00 130.00   0.50    0.50    --   40.90 -11.00   0.00  100
 16  \w     22.00  68.00   0.50    0.50    --   40.90 -82.00 -16.42   92
 17  \w     22.00  89.00   0.50    0.50    --   40.90  65.00  30.00  134
 18  \w     69.00 125.00   0.50    0.50    --   40.90  77.00 -60.00  112
 19  \w     43.00  68.00   0.50    0.50    --   40.90 -82.00   0.00   50
 20  \w    101.00 126.00   0.50    0.50    --   40.90  65.00  30.00   50
 21  \w     18.00  43.00   0.50    0.50    --   40.90  77.00-180.00   50
 22  \w     56.00  81.00   0.50    0.50    --   40.90  77.00-180.00   50
 23  \w     44.00  98.00   0.50    0.50    --   93.40 -82.00  60.00  108
 24  \w      4.00 109.00   0.50    0.50    --   93.40 -82.00 -30.00  210
 25  \w      4.00 167.00   0.50    0.50    --   93.40 -17.00 -30.00  326
 26  \w    137.00 180.00   0.50    0.50    --   93.40  68.00 120.00   86
 27  \w     92.00 118.00   0.50    0.50    --   93.40  68.00 120.00   52
 28  \w      4.00  96.00   0.50    0.50    --   93.40 -82.00-180.00  184
 29  \w     39.00  94.00   0.50    0.50    --   93.40 -82.00-120.00  110
 30  \w     54.00 100.00   0.50    0.50    --   93.40 -82.00 120.00   92
 31  \w      4.00 131.00   0.50    0.50    --   93.40 -33.00 150.00  254
 32  \w     60.00 127.00   0.50    0.50    --   93.40 -50.00 -60.00  134
 33  \w     66.00 183.00   0.50    0.50    --   93.40  59.00 150.00  234
 34  \w     66.00 106.00   0.50    0.50    --   93.40 -82.00   0.00   80
 35  \w      4.00  30.00   0.50    0.50    --   93.40 -50.00 -60.00   52
 36  \w     34.00  61.00   0.50    0.50    --   93.40 -77.00 150.00   54
 37  \w     24.00  97.00   0.50    0.50    --   93.40 -82.00  90.00  146
 38  \w     10.00 145.00   0.50    0.50    --   93.40   8.00 -60.00  270
 39  \w     71.00 101.00   0.50    0.50    --   93.40 -82.00-150.00   60
 40  \w     68.00  95.00   0.50    0.50    --   93.40 -82.00 150.00   54
 41  \w     32.00  66.00   0.50    0.50    --   93.40 -82.00-150.00   68
 42  \w     32.00  95.00   0.50    0.50    --   93.40 -82.00 -90.00  126
 43  \w     66.00  96.00   0.50    0.50    --   93.40 -82.00 -60.00   60
 44  \w     53.00  78.00   0.50    0.50    --   93.40 -82.00  30.00   50
 45  \w     15.00  49.00   0.50    0.50    --   93.40 -59.00  90.00   68
 46  \w     17.00  63.00   0.50    0.50    --   93.40 -82.00 -60.00   92
;
_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      0.0766083000
_diffrn_orient_matrix_UB_12      0.0028620000
_diffrn_orient_matrix_UB_13      0.0171822000
_diffrn_orient_matrix_UB_21      -0.0057689000
_diffrn_orient_matrix_UB_22      -0.1122060000
_diffrn_orient_matrix_UB_23      -0.0578771000
_diffrn_orient_matrix_UB_31      -0.0082874000
_diffrn_orient_matrix_UB_32      0.0996199000
_diffrn_orient_matrix_UB_33      -0.0656847000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35691
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.751
_diffrn_reflns_theta_min         2.218
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75303
_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_density_diffrn    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0709P)^2^+1.9153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4612
_reflns_number_total             6709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01702k2.cif
_cod_data_source_block           exp_285_sq
_cod_depositor_comments
'Adding full bibliography for 7158307--7158313.cif.'
_cod_database_code               7158313
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_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 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:
 C01B(H01E,H01F)
2.b Aromatic/amide H refined with riding coordinates:
 N008(H008), C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00V(H00V), C00W(H00W), C00X(H00X), C010(H010), C011(H011), C013(H013),
 C014(H014), C015(H015), C017(H017), C018(H018), C01A(H01D), C01C(H01G)
2.c Idealised Me refined as rotating group:
 C016(H01A,H01B,H01C), C01E(H01H,H01I,H01J), C01F(H01K,H01L,H01M)
;
_shelx_res_checksum              57930
_shelx_fab_checksum              64589
_platon_squeeze_void_probe_radius 1.20
_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 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.717