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_7158312
_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 O7 S2'
_chemical_formula_sum            'C36 H29 Cl N2 O7 S2'
_chemical_formula_weight         701.18
_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
_audit_creation_date             2020-06-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-06-27 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.144(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.3232(11)
_cell_length_b                   11.8905(3)
_cell_length_c                   26.1613(10)
_cell_measurement_reflns_used    6987
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.7270
_cell_measurement_theta_min      3.4110
_cell_volume                     8039.8(5)
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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     19.00 129.00   0.50    0.50    --   40.90  54.00 120.00  220
  2  \w     15.00  63.00   0.50    0.50    --   40.90  82.00   0.00   96
  3  \w    -47.00  65.00   0.50    0.50    --   40.90 -77.00 -60.00  224
  4  \w    -49.00  15.00   0.50    0.50    --   40.90 -43.00  30.00  128
  5  \w     23.00  67.00   0.50    0.50    --   40.90 -82.00-120.00   88
  6  \w     67.00 102.00   0.50    0.50    --   40.90  82.00   0.00   70
  7  \w     23.00  68.00   0.50    0.50    --   40.90 -82.00 120.00   90
  8  \w    -44.00 -18.00   0.50    0.50    --   40.90 -82.00  30.00   52
  9  \w     31.00  63.00   0.50    0.50    --   40.90 -82.00-150.00   64
 10  \w     46.00  72.00   0.50    0.50    --   40.90 -43.00  30.00   52
 11  \w    -41.00  42.00   0.50    0.50    --   40.90 -82.00-180.00  166
 12  \w    -44.00 -19.00   0.50    0.50    --   40.90 -43.00-150.00   50
 13  \w    -14.00  51.00   0.50    0.50    --   40.90 -43.00-150.00  130
 14  \w    -47.00 -22.00   0.50    0.50    --   40.90 -82.00-120.00   50
 15  \w    -39.00  -2.00   0.50    0.50    --   40.90 -77.00 -90.00   74
 16  \w     36.00  68.00   0.50    0.50    --   40.90 -82.00  30.00   64
 17  \w     31.00  68.00   0.50    0.50    --   40.90 -82.00 150.00   74
 18  \w    -32.00  12.00   0.50    0.50    --   40.90 -82.00 150.00   88
 19  \w     26.00  61.00   0.50    0.50    --   40.90 -54.00 -30.00   70
 20  \w    -25.00   0.00   0.50    0.50    --   40.90 -54.00 -30.00   50
 21  \w     18.00  67.00   0.50    0.50    --   40.90 -82.00 -30.00   98
 22  \w     60.00  96.00   0.50    0.50    --   93.40 -82.00 -90.00   72
 23  \w     76.00 101.00   0.50    0.50    --   93.40 -82.00 120.00   50
 24  \w     41.00  67.00   0.50    0.50    --   93.40 -82.00 120.00   52
 25  \w     19.00 127.00   0.50    0.50    --   93.40 -50.00   0.00  216
 26  \w      4.00  82.00   0.50    0.50    --   93.40 -33.00 120.00  156
 27  \w     71.00  98.00   0.50    0.50    --   93.40 -82.00  30.00   54
 28  \w      4.00 183.00   0.50    0.50    --   93.40   8.00  30.00  358
 29  \w     39.00  65.00   0.50    0.50    --   93.40 -82.00  30.00   52
 30  \w     54.00 120.00   0.50    0.50    --   93.40  33.00 -30.00  132
 31  \w     45.00  94.00   0.50    0.50    --   93.40 -82.00-120.00   98
 32  \w     62.00  96.00   0.50    0.50    --   93.40 -82.00 -60.00   68
 33  \w     78.00 104.00   0.50    0.50    --   93.40 -82.00  90.00   52
 34  \w      4.00 125.00   0.50    0.50    --   93.40 -50.00-150.00  242
 35  \w     25.00 100.00   0.50    0.50    --   93.40 -82.00 150.00  150
 36  \w     17.00 107.00   0.50    0.50    --   93.40 -82.00   0.00  180
 37  \w     70.00  95.00   0.50    0.50    --   93.40 -82.00-180.00   50
 38  \w     36.00 121.00   0.50    0.50    --   93.40 -82.00-150.00  170
 39  \w    151.00 183.00   0.50    0.50    --   93.40  33.00 -30.00   64
 40  \w     35.00  63.00   0.50    0.50    --   93.40 -82.00-180.00   56
 41  \w     71.00  97.00   0.50    0.50    --   93.40 -82.00  60.00   52
 42  \w    115.00 154.00   0.50    0.50    --   93.40  50.00  60.00   78
 43  \w     29.00  96.00   0.50    0.50    --   93.40 -82.00 -30.00  134
 44  \w     79.00 104.00   0.50    0.50    --   93.40  68.00 -30.00   50
 45  \w     92.00 125.00   0.50    0.50    --   93.40 -33.00 120.00   66
 46  \w     40.00 146.00   0.50    0.50    --   93.40 -25.00 -30.00  212
 47  \w      7.00  33.00   0.50    0.50    --   93.40 -25.00 -30.00   52
;
_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      0.0446459000
_diffrn_orient_matrix_UB_12      -0.0154822000
_diffrn_orient_matrix_UB_13      -0.0185835000
_diffrn_orient_matrix_UB_21      0.0387014000
_diffrn_orient_matrix_UB_22      -0.0082940000
_diffrn_orient_matrix_UB_23      0.0617569000
_diffrn_orient_matrix_UB_31      -0.0078524000
_diffrn_orient_matrix_UB_32      -0.1284230000
_diffrn_orient_matrix_UB_33      -0.0017384000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            36767
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.428
_diffrn_reflns_theta_max         67.427
_diffrn_reflns_theta_min         3.420
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45880
_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    1.159
_exptl_crystal_description       block
_exptl_crystal_F_000             2912
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0875P)^2^+7.6366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.1957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4837
_reflns_number_total             7132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01702k2.cif
_cod_data_source_block           zhoujie1_sq
_cod_depositor_comments
'Adding full bibliography for 7158307--7158313.cif.'
_cod_database_code               7158312
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 98.96
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00P(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C01E(H01G,H01H)
2.c Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00O(H00O), C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C011(H011), C012(H012), C013(H013), C015(H015), C016(H016),
 C018(H018), C019(H019), C01A(H01D), C01B(H01E), C01D(H01F)
2.d Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C), C01F(H01I,H01J,H01K), C01I(H01L,H01M,H01N)
;
_shelx_res_checksum              33304
_shelx_fab_checksum              63839
_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 2.378
_oxdiff_exptl_absorpt_empirical_full_min 0.436