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_4024667
_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         'C17 H13 Br F N O S'
_chemical_formula_sum            'C17 H13 Br F N O S'
_chemical_formula_weight         378.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 107.787(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   9.924(5)
_cell_length_b                   17.654(5)
_cell_length_c                   9.340(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.3
_cell_volume                     1558.1(12)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9993
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    2.783
_exptl_absorpt_correction_T_max  0.7494
_exptl_absorpt_correction_T_min  0.6967
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.185
_refine_diff_density_min         -1.477
_refine_diff_density_rms         0.205
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0176P)^2^+12.0934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2927
_reflns_number_total             3820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900615p_si_002_2.cif
_cod_data_source_block           compound7d
_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 
;
_cod_original_sg_symbol_H-M      p_1_21/c_1
_cod_database_code               4024667