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_7062565
_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            'C30 H24 N2 O3 S2'
_chemical_formula_weight         524.63
_chemical_melting_point          447.5(5)
_chemical_name_systematic
(S)-4-((4-oxo-6-tosyl-1,2,3,4,6,11c-hexahydrobenzo[4,5]thieno[2,3-c]isoquinolin-5-yl)methyl)benzonitrile
_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
;
2023-04-06 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                   10.378(2)
_cell_length_b                   13.432(3)
_cell_length_c                   18.562(4)
_cell_measurement_reflns_used    8856
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.41
_cell_measurement_theta_min      2.19
_cell_volume                     2587.5(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1196
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            58680
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.104
_diffrn_reflns_theta_max         25.104
_diffrn_reflns_theta_min         2.480
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/petroleum ether'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4590
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0615P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3016
_reflns_number_total             4590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02798h2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '447-448' was changed to
'447.5(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        2587.7(10)
_cod_database_code               7062565
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              67207