Organocatalytic stereoselective construction of polycyclic benzo[b]thiophenes from 2-aminobenzo[b]thiophenes and alkynyl-substituted enones
Niu, Cheng; Zheng, Yao; Du, Da-Ming; New Journal of Chemistry 47 (2023) 14515–14519; doi:10.1039/D3NJ02798H

data_7062566
_publ_section_title
;
 Organocatalytic stereoselective construction of polycyclic
 benzo[b]thiophenes from 2-aminobenzo[b]thiophenes and alkynyl-substituted
 enones
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14515
_journal_page_last               14519
_journal_paper_doi               10.1039/D3NJ02798H
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C35 H28 N2 O2 S2'
_chemical_formula_weight         572.71
_chemical_melting_point          442.5(5)
_chemical_name_systematic
'(5bS,12cS,Z)-6-benzylidene-7-tosyl-5b,6,7,12c,13,14-hexahydro-5H-benzo[4',5']thieno- [3',2':5,6]pyrido[3,4-a]carbazole'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-06-17 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6474(14)
_cell_length_b                   13.1696(19)
_cell_length_c                   22.923(3)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      66.31
_cell_measurement_theta_min      3.86
_cell_volume                     2912.4(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30681
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.366
_diffrn_reflns_theta_max         67.366
_diffrn_reflns_theta_min         3.857
_exptl_absorpt_coefficient_mu    1.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       Block
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Perroleum ether/chloroform 1:1'
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1264 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.090(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0706
_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^)+(0.1428P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.2164
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3761
_reflns_number_total             5189
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02798h2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '442-443' was changed to
'442.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7062565--7062566.cif.
;
_cod_original_cell_volume        2912.5(7)
_cod_database_code               7062566
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.801
_shelx_estimated_absorpt_t_max   0.861
_shelx_res_checksum              3268