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_7158311
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-07-04
_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                86.651(2)
_cell_angle_beta                 78.773(2)
_cell_angle_gamma                67.019(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8359(2)
_cell_length_b                   11.1243(3)
_cell_length_c                   17.4373(4)
_cell_measurement_reflns_used    11866
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.2520
_cell_measurement_theta_min      2.6050
_cell_volume                     1897.71(8)
_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(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.957
_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     35.00  83.00   0.50    0.50    --   40.70  79.00 121.00   96
  2  \w     88.00 129.00   0.50    0.50    --   40.70  79.00 121.00   82
  3  \w      5.00  31.00   0.50    0.50    --   93.40 -79.00  -2.00   52
  4  \w     70.00 183.00   0.50    0.50    --   93.40  79.00 121.00  226
  5  \w     12.00  39.00   0.50    0.50    --   40.70 -77.00  30.00   54
  6  \w    -48.00  13.00   0.50    0.50    --   40.70 -54.00-150.00  122
  7  \w    -46.00  65.00   0.50    0.50    --   40.70 -65.00  60.00  222
  8  \w    -26.00  -1.00   0.50    0.50    --   40.70 -65.00-120.00   50
  9  \w      8.00  73.00   0.50    0.50    --   40.70  54.00-120.00  130
 10  \w     34.00  68.00   0.50    0.50    --   40.70 -82.00-150.00   68
 11  \w    -42.00  63.00   0.50    0.50    --   40.70 -82.00 -30.00  210
 12  \w    -43.00 -18.00   0.50    0.50    --   40.70 -82.00  30.00   50
 13  \w     36.00  61.00   0.50    0.50    --   40.70 -43.00  30.00   50
 14  \w      7.00  37.00   0.50    0.50    --   40.70 -65.00-120.00   60
 15  \w     38.00  67.00   0.50    0.50    --   40.70 -82.00  90.00   58
 16  \w     82.00 120.00   0.50    0.50    --   40.70  54.00-120.00   76
 17  \w     21.00  46.00   0.50    0.50    --   40.70 -43.00 -90.00   50
 18  \w    -46.00  -1.00   0.50    0.50    --   40.70 -43.00 -90.00   90
 19  \w     28.00  54.00   0.50    0.50    --   40.70 -79.00  -2.00   52
 20  \w    -44.00  12.00   0.50    0.50    --   40.70 -79.00  -2.00  112
 21  \w      4.00  29.00   0.50    0.50    --   40.70 -82.00-150.00   50
 22  \w     -5.00  66.00   0.50    0.50    --   40.70 -82.00  30.00  142
 23  \w    -14.00  68.00   0.50    0.50    --   40.70 -82.00-180.00  164
 24  \w    -46.00 -21.00   0.50    0.50    --   40.70 -82.00-150.00   50
 25  \w     46.00  71.00   0.50    0.50    --   40.70 -54.00-150.00   50
 26  \w      4.00 120.00   0.50    0.50    --   93.40 -82.00-180.00  232
 27  \w     48.00  99.00   0.50    0.50    --   93.40 -82.00  60.00  102
 28  \w    106.00 183.00   0.50    0.50    --   93.40  42.00   0.00  154
 29  \w      6.00 121.00   0.50    0.50    --   93.40 -82.00 -60.00  230
 30  \w      4.00  92.00   0.50    0.50    --   93.40 -50.00  30.00  176
 31  \w     70.00  96.00   0.50    0.50    --   93.40  42.00   0.00   52
 32  \w      9.00  95.00   0.50    0.50    --   93.40 -68.00-180.00  172
 33  \w      4.00 118.00   0.50    0.50    --   93.40 -82.00 150.00  228
 34  \w     78.00 104.00   0.50    0.50    --   93.40 -82.00-120.00   52
 35  \w    110.00 136.00   0.50    0.50    --   93.40  68.00  60.00   52
 36  \w     76.00 102.00   0.50    0.50    --   93.40 -82.00  30.00   52
 37  \w     29.00  94.00   0.50    0.50    --   93.40 -82.00 -90.00  130
 38  \w     60.00 174.00   0.50    0.50    --   93.40  50.00  90.00  228
 39  \w     60.00 103.00   0.50    0.50    --   93.40 -82.00 -30.00   86
 40  \w    158.00 183.00   0.50    0.50    --   93.40  82.00  90.00   50
 41  \w    110.00 169.00   0.50    0.50    --   93.40  33.00  60.00  118
 42  \w    114.00 140.00   0.50    0.50    --   93.40  68.00 -60.00   52
 43  \w     66.00 173.00   0.50    0.50    --   93.40  82.00 150.00  214
 44  \w      5.00  95.00   0.50    0.50    --   93.40 -42.00-180.00  180
 45  \w     81.00 123.00   0.50    0.50    --   93.40  82.00  90.00   84
 46  \w     74.00  99.00   0.50    0.50    --   93.40 -82.00-150.00   50
 47  \w     59.00  84.00   0.50    0.50    --   93.40 -82.00   0.00   50
 48  \w     58.00  95.00   0.50    0.50    --   93.40 -82.00 120.00   74
 49  \w     81.00 176.00   0.50    0.50    --   93.40  59.00  30.00  190
 50  \w     70.00  95.00   0.50    0.50    --   93.40 -82.00  90.00   50
 51  \w     68.00  97.00   0.50    0.50    --   93.40  33.00  60.00   58
;
_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      -0.0775598000
_diffrn_orient_matrix_UB_12      0.1280720000
_diffrn_orient_matrix_UB_13      -0.0390122000
_diffrn_orient_matrix_UB_21      -0.0113608000
_diffrn_orient_matrix_UB_22      -0.0789481000
_diffrn_orient_matrix_UB_23      -0.0661099000
_diffrn_orient_matrix_UB_31      -0.1362644000
_diffrn_orient_matrix_UB_32      0.0008762000
_diffrn_orient_matrix_UB_33      0.0471558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19436
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.812
_diffrn_reflns_theta_min         2.584
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.309
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02222
_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    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0796
_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^)+(0.1469P)^2^+1.8080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2302
_refine_ls_wR_factor_ref         0.2366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5610
_reflns_number_total             6575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01702k2.cif
_cod_data_source_block           exp_245_sq
_cod_depositor_comments
'Adding full bibliography for 7158307--7158313.cif.'
_cod_database_code               7158311
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
01e2cdd4077f9c789bfbe730f54c84c90000029eca3
;
_diffrn_oxdiff_digest_hkl
;
01ac1b9cbeaada5b9428a9009fe00ab113c645
;
_reflns_odcompleteness_completeness 97.06
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C4(H4), C17(H17), C27(H27), C31(H31), C14(H14), C11(H11),
 C47(H47), C30(H30), C28(H28), C29(H29), C46(H46), C43(H43), C13(H13), C12(H12),
  C44(H44)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C40(H40A,H40B,H40C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              79951
_shelx_fab_checksum              32809
_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 10.801
_oxdiff_exptl_absorpt_empirical_full_min 0.386