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_7158308
_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 H30 Cl N2 O5 S2'
_chemical_formula_weight         670.19
_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     dual
_audit_creation_date             2019-06-15
_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                 97.4240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.39340(10)
_cell_length_b                   18.0084(3)
_cell_length_c                   17.5835(3)
_cell_measurement_reflns_used    8153
_cell_measurement_temperature    179.98(10)
_cell_measurement_theta_max      75.5550
_cell_measurement_theta_min      4.2850
_cell_volume                     3263.49(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      179.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_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     53.00  80.00   0.50    5.00    --  109.88 -71.00  17.00   54
  2  \w     84.00 132.00   0.50    5.00    --  109.88 -71.00  17.00   96
  3  \w     74.00 107.00   0.50    5.00    --  109.88 -94.00 -30.00   66
  4  \w     51.00 120.00   0.50    5.00    --  109.88-125.00   0.00  138
  5  \w     41.00  81.00   0.50    5.00    --  109.88 -94.00 -60.00   80
  6  \w     37.00  92.00   0.50    5.00    --  109.88 -94.00-120.00  110
  7  \w     -4.00  21.00   0.50    2.00    --   43.18 -71.00  17.00   50
  8  \w     37.00  92.00   0.50    5.00    --  109.88 -94.00 150.00  110
  9  \w     90.00 178.00   0.50    5.00    --  109.88  45.00  90.00  176
 10  \w     87.00 177.00   0.50    5.00    --  109.88  71.00 148.00  180
 11  \w     89.00 178.00   0.50    5.00    --  109.88  61.00-180.00  178
 12  \w    -68.00  29.00   0.50    2.00    --  -43.18  71.00 148.00  194
 13  \w    -91.00 -66.00   0.50    5.00    --  -90.25  71.00 148.00   50
 14  \w    -94.00 -59.00   0.50    5.00    --  -90.25 125.00  60.00   70
 15  \w    -81.00 -49.00   0.50    5.00    --  -90.25 125.00-180.00   64
 16  \w   -104.00 -17.00   0.50    2.00    --  -43.18 -71.00  17.00  174
 17  \w   -116.00 -71.00   0.50    2.00    --  -43.18-125.00 150.00   90
 18  \w   -110.00 -70.00   0.50    2.00    --  -43.18-125.00 120.00   80
 19  \w   -139.00-113.00   0.50    5.00    --  -90.25 -71.00  17.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0771600000
_diffrn_orient_matrix_UB_12      -0.0083603000
_diffrn_orient_matrix_UB_13      -0.0686550000
_diffrn_orient_matrix_UB_21      -0.0840115000
_diffrn_orient_matrix_UB_22      -0.0674353000
_diffrn_orient_matrix_UB_23      -0.0284476000
_diffrn_orient_matrix_UB_31      -0.0965747000
_diffrn_orient_matrix_UB_32      0.0519493000
_diffrn_orient_matrix_UB_33      -0.0478408000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.911
_diffrn_reflns_theta_min         3.528
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             1396
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.438
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0748P)^2^+1.8405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5608
_reflns_number_total             6586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01702k2.cif
_cod_data_source_block           exp_2650
_cod_depositor_comments
'Adding full bibliography for 7158307--7158313.cif.'
_cod_database_code               7158308
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.623
_shelx_estimated_absorpt_t_min   0.623
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00D(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011),
 C012(H012), C013(H013), C014(H014), C015(H015), C016(H016)
2.d Idealised Me refined as rotating group:
 C018(H01A,H01B,H01C), C01A(H01D,H01E,H01F), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              2060
_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 1.139
_oxdiff_exptl_absorpt_empirical_full_min 0.906