Construction of Benzothiophene or Benzothiopheno[2,3-<i>e</i>]azepinedione Derivatives via Three-Component Domino or One-Pot Sequences.
Deng, Qingsong; Yu, Aimin; Zhou, Jie; Cao, Qin; Meng, Xiangtai; The Journal of organic chemistry 85 (2020) 12270–12283; doi:10.1021/acs.joc.0c01505

data_4038803
_publ_section_title
;
 Construction of Benzothiophene or
 Benzothiopheno[2,3-<i>e</i>]azepinedione Derivatives via Three-Component
 Domino or One-Pot Sequences.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12270
_journal_page_last               12283
_journal_paper_doi               10.1021/acs.joc.0c01505
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C21 H21 N O2 S'
_chemical_formula_sum            'C21 H21 N O2 S'
_chemical_formula_weight         351.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.6005(7)
_cell_length_b                   9.3977(3)
_cell_length_c                   18.9366(7)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      64.45
_cell_measurement_theta_min      4.09
_cell_volume                     3844.0(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      273.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.3198
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            91539
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.103
_diffrn_reflns_theta_max         67.103
_diffrn_reflns_theta_min         4.093
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Flack x determined using 2282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.61(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.457
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6824
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.457
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0898
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2087
_refine_ls_wR_factor_ref         0.2227
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                5630
_reflns_number_total             6824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01505_si_002.cif
_cod_data_source_block           deng0728-2
_cod_depositor_comments
;
Adding full bibliography for 4038801--4038807.cif.

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C41 H40 N2 O4 S2'
_cod_original_formula_weight         688.87
_cod_original_formula_moiety         '2(C21 H21 N O2 S)'
_cod_original_formula_units_Z            4
_cod_database_code               4038803
_shelx_shelxl_version_number     2017/1
_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:
 C00Q(H00A,H00B), C011(H01A,H01B), C017(H01F,H01G), C018(H01M,H01N), C019(H01O,
 H01P), C01D(H01H,H01I)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005), N007(H007), C009(H009), C00M(H00M), C00R(H00R), C00S(H00S),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C012(H012), C015(H015), C016(H016), C01A(H01Q), C01C(H01U)
2.c Idealised Me refined as rotating group:
 C013(H01C,H01D,H01E), C014(H01J,H01K,H01L), C01B(H01R,H01S,H01T), C1(H1A,H1B,
 H1C)
;
_shelx_res_checksum              41785
_shelx_hkl_checksum              92345
_shelx_fab_checksum              65108
_olex2_submission_special_instructions 'No special instructions were received'