Novel Route to 2,3-Substituted Benzo[b]thiophenes via Intramolecular Radical Cyclization
Prabal P. Singh; A. K. Yadav; H. Ila; H. Junjappa; Journal of Organic Chemistry 74 (2009) 5496–5501; doi:10.1021/jo900615p

data_4024669
_publ_contact_author_address
;
Department of Chemistry
Indian Institute of Technology
Kanpur 208016
India
;
_publ_contact_author_name        'Pro.  H. Ila'
_publ_section_title
;
Novel Route to 2,3-Substituted Benzo[b]thiophenes via Intramolecular
Radical Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5496
_journal_page_last               5501
_journal_paper_doi               10.1021/jo900615p
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C15 H10 Br F N2 S'
_chemical_formula_sum            'C15 H10 Br F N2 S'
_chemical_formula_weight         349.22
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 127.953(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   25.912(5)
_cell_length_b                   6.972(5)
_cell_length_c                   19.546(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.0
_cell_volume                     2784(2)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8765
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    3.103
_exptl_absorpt_correction_T_max  0.7071
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+24.6524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                2501
_reflns_number_total             3413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900615p_si_002_4.cif
_cod_data_source_block           Compound7K
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

2020-10-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_moiety     'C30 H20 Br2 F2 N4 S2'
_cod_original_formula_sum        'C30 H20 Br2 F2 N4 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     698.44
_cod_database_code               4024669