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_7158309
_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 H31 Cl N2 O5 S2'
_chemical_formula_sum            'C36 H31 Cl N2 O5 S2'
_chemical_formula_weight         671.20
_chemical_name_systematic        221
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-08-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-27 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.720(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2429(6)
_cell_length_b                   9.7717(2)
_cell_length_c                   28.6043(7)
_cell_measurement_reflns_used    6842
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.2760
_cell_measurement_theta_min      3.0770
_cell_volume                     6474.7(3)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.973
_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     10.00  78.00   0.50    0.50    --   40.90 -32.00-120.00  136
  2  \w    -49.00  -2.00   0.50    0.50    --   40.90 -54.00   0.00   94
  3  \w     40.00  73.00   0.50    0.50    --   40.90 -54.00 -60.00   66
  4  \w      7.00  68.00   0.50    0.50    --   40.90 -82.00 -60.00  122
  5  \w    -48.00  -1.00   0.50    0.50    --   40.90 -77.00 120.00   94
  6  \w     43.00  72.00   0.50    0.50    --   40.90 -54.00   0.00   58
  7  \w     37.00  67.00   0.50    0.50    --   40.90 -82.00 -30.00   60
  8  \w    -44.00  -5.00   0.50    0.50    --   40.90 -82.00-180.00   78
  9  \w    -25.00   3.00   0.50    0.50    --   40.90 -82.00-150.00   56
 10  \w    -48.00 -20.00   0.50    0.50    --   40.90 -82.00  60.00   56
 11  \w    -38.00 -13.00   0.50    0.50    --   40.90 -82.00 -60.00   50
 12  \w      3.00  38.00   0.50    0.50    --   40.90 -77.00 120.00   70
 13  \w     26.00  55.00   0.50    0.50    --   40.90 -65.00-120.00   58
 14  \w    -46.00  18.00   0.50    0.50    --   40.90 -65.00-120.00  128
 15  \w      9.00  48.00   0.50    0.50    --   40.90 -77.00 150.00   78
 16  \w     16.00  68.00   0.50    0.50    --   40.90 -82.00-180.00  104
 17  \w     49.00  74.00   0.50    0.50    --   40.90  65.00 -90.00   50
 18  \w    -16.00  67.00   0.50    0.50    --   40.90 -82.00  60.00  166
 19  \w    -30.00  -5.00   0.50    0.50    --   40.90 -54.00 -60.00   50
 20  \w     24.00  68.00   0.50    0.50    --   40.90 -82.00-150.00   88
 21  \w    -24.00   3.00   0.50    0.50    --   40.90 -77.00 150.00   54
 22  \w     35.00  61.00   0.50    0.50    --   40.90  82.00  30.00   52
 23  \w    -47.00 -22.00   0.50    0.50    --   40.90 -32.00-120.00   50
 24  \w      4.00 121.00   0.50    0.50    --   93.40 -59.00 -30.00  234
 25  \w     88.00 114.00   0.50    0.50    --   93.40 -59.00 150.00   52
 26  \w      4.00 183.00   0.50    0.50    --   93.40   0.00-120.00  358
 27  \w      4.00  81.00   0.50    0.50    --   93.40 -59.00 150.00  154
 28  \w     67.00  93.00   0.50    0.50    --   93.40 -82.00 -60.00   52
 29  \w     56.00 102.00   0.50    0.50    --   93.40 -82.00-150.00   92
 30  \w     18.00  61.00   0.50    0.50    --   93.40 -33.00-180.00   86
 31  \w     87.00 133.00   0.50    0.50    --   93.40 -33.00 150.00   92
 32  \w     78.00 103.00   0.50    0.50    --   93.40 -82.00 150.00   50
 33  \w     66.00  92.00   0.50    0.50    --   93.40 -82.00-180.00   52
 34  \w     59.00 101.00   0.50    0.50    --   93.40 -82.00  60.00   84
 35  \w      4.00 121.00   0.50    0.50    --   93.40 -82.00 120.00  234
 36  \w    126.00 152.00   0.50    0.50    --   93.40  59.00-120.00   52
 37  \w     24.00  62.00   0.50    0.50    --   93.40 -77.00 -60.00   76
 38  \w     71.00  96.00   0.50    0.50    --   93.40 -82.00  90.00   50
 39  \w      4.00  72.00   0.50    0.50    --   93.40 -33.00 150.00  136
 40  \w     67.00  93.00   0.50    0.50    --   93.40 -82.00-120.00   52
 41  \w     88.00 124.00   0.50    0.50    --   93.40 -33.00   0.00   72
 42  \w     19.00  65.00   0.50    0.50    --   93.40 -82.00  90.00   92
 43  \w     20.00  48.00   0.50    0.50    --   93.40 -33.00   0.00   56
 44  \w     84.00 114.00   0.50    0.50    --   93.40 -33.00-180.00   60
 45  \w     12.00  94.00   0.50    0.50    --   93.40 -82.00 -90.00  164
 46  \w      9.00 115.00   0.50    0.50    --   93.40 -33.00 -30.00  212
 47  \w     18.00  71.00   0.50    0.50    --   93.40 -82.00 150.00  106
 48  \w     84.00 110.00   0.50    0.50    --   93.40 -82.00   0.00   52
 49  \w     10.00 101.00   0.50    0.50    --   93.40 -82.00 -30.00  182
;
_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      -0.0236413000
_diffrn_orient_matrix_UB_12      -0.0541727000
_diffrn_orient_matrix_UB_13      -0.0484011000
_diffrn_orient_matrix_UB_21      -0.0112113000
_diffrn_orient_matrix_UB_22      -0.1405076000
_diffrn_orient_matrix_UB_23      0.0219162000
_diffrn_orient_matrix_UB_31      -0.0611328000
_diffrn_orient_matrix_UB_32      0.0467427000
_diffrn_orient_matrix_UB_33      0.0098662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            27996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.663
_diffrn_reflns_theta_min         3.100
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34490
_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 whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             2800
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         5825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0775P)^2^+3.9035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4253
_reflns_number_total             5825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01702k2.cif
_cod_data_source_block           mxt-3
_cod_depositor_comments
'Adding full bibliography for 7158307--7158313.cif.'
_cod_database_code               7158309
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.858
_diffrn_oxdiff_digest_frames
;
01001d5318ef37c7ebe0243efed19b027200030efee
;
_diffrn_oxdiff_digest_hkl
;
01b46c2bb0d7e157abf8ae0434fbad2b83f955
;
_reflns_odcompleteness_completeness 99.69
_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:
 C15(H15), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C12(H12), C17(H17), C20(H20), C7(H7), C45(H45), C31(H31), C6(H6),
 C18(H18), C41(H41), C27(H27), C19(H19), C44(H44), C42(H42), C30(H30), C28(H28),
  C29(H29)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C46(H46A,H46B,H46C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              1008
_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 4.265
_oxdiff_exptl_absorpt_empirical_full_min 0.604