#------------------------------------------------------------------------------
#$Date: 2020-11-05 10:56:28 +0200 (Thu, 05 Nov 2020) $
#$Revision: 258736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/46/4024669.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024669
loop_
_publ_author_name
'Prabal P. Singh'
'A. K. Yadav'
'H. Ila'
'H. Junjappa'
_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
_chemical_name_systematic
;
 ?
;
_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/[σ²(Fo²)+(0.0328P)²+24.6524P] where P=(Fo²+2Fc²)/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_formula_sum            'C30 H20 Br2 F2 N4 S2'
_cod_original_formula_weight         698.44
_cod_original_formula_moiety         'C30 H20 Br2 F2 N4 S2'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4024669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.95841(2) -0.37942(7) 0.88682(3) 0.02882(16) Uani 1 1 d . . .
S1 S 0.79249(5) -0.05483(18) 0.57104(7) 0.0227(3) Uani 1 1 d . . .
F1 F 1.13766(13) 0.1357(4) 1.05327(17) 0.0317(7) Uani 1 1 d . . .
N2 N 0.82921(17) 0.3057(5) 0.8241(2) 0.0204(8) Uani 1 1 d . . .
C3 C 0.9647(2) -0.0243(6) 0.8192(3) 0.0198(9) Uani 1 1 d . . .
C2 C 0.9059(2) -0.0878(6) 0.7319(3) 0.0211(9) Uani 1 1 d . . .
N1 N 0.92095(19) -0.3950(6) 0.6708(2) 0.0263(9) Uani 1 1 d . . .
C11 C 0.8332(2) 0.1760(6) 0.7126(3) 0.0177(8) Uani 1 1 d . . .
C7 C 1.0506(2) 0.2125(7) 0.9076(3) 0.0256(10) Uani 1 1 d . . .
H7 H 1.0688 0.3321 0.9134 0.031 Uiso 1 1 calc R . .
C10 C 0.7137(2) -0.0158(7) 0.5459(3) 0.0247(10) Uani 1 1 d . . .
H10A H 0.6798 -0.0495 0.4865 0.037 Uiso 1 1 calc R . .
H10B H 0.7095 0.1169 0.5548 0.037 Uiso 1 1 calc R . .
H10C H 0.7100 -0.0939 0.5831 0.037 Uiso 1 1 calc R . .
C5 C 1.0551(2) -0.0916(6) 0.9711(3) 0.0215(9) Uani 1 1 d . . .
H5 H 1.0763 -0.1741 1.0185 0.026 Uiso 1 1 calc R . .
C9 C 0.8487(2) 0.0119(6) 0.6810(3) 0.0197(9) Uani 1 1 d . . .
C8 C 0.9929(2) 0.1550(6) 0.8296(3) 0.0205(9) Uani 1 1 d . . .
H8 H 0.9722 0.2384 0.7826 0.025 Uiso 1 1 calc R . .
C15 C 0.8429(2) 0.1641(7) 0.7911(3) 0.0205(9) Uani 1 1 d . . .
H15 H 0.8600 0.0506 0.8225 0.025 Uiso 1 1 calc R . .
C4 C 0.9968(2) -0.1430(6) 0.8920(3) 0.0177(8) Uani 1 1 d . . .
C13 C 0.7904(2) 0.4909(7) 0.6973(3) 0.0254(10) Uani 1 1 d . . .
H13 H 0.7718 0.6045 0.6665 0.030 Uiso 1 1 calc R . .
C14 C 0.8036(2) 0.4654(7) 0.7773(3) 0.0231(9) Uani 1 1 d . . .
H14 H 0.7939 0.5653 0.7993 0.028 Uiso 1 1 calc R . .
C12 C 0.8053(2) 0.3457(7) 0.6647(3) 0.0229(10) Uani 1 1 d . . .
H12 H 0.7970 0.3597 0.6114 0.027 Uiso 1 1 calc R . .
C1 C 0.9138(2) -0.2577(7) 0.6966(3) 0.0223(9) Uani 1 1 d . . .
C6 C 1.0801(2) 0.0865(7) 0.9763(3) 0.0232(10) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C10 103.9(2) . . ?
C14 N2 C15 117.0(4) . . ?
C4 C3 C8 116.8(4) . . ?
C4 C3 C2 122.6(4) . . ?
C8 C3 C2 120.4(4) . . ?
C9 C2 C1 118.6(4) . . ?
C9 C2 C3 124.8(4) . . ?
C1 C2 C3 116.3(4) . . ?
C15 C11 C12 117.0(4) . . ?
C15 C11 C9 120.3(4) . . ?
C12 C11 C9 122.6(4) . . ?
C6 C7 C8 117.7(4) . . ?
C6 C5 C4 117.2(4) . . ?
C2 C9 C11 123.1(4) . . ?
C2 C9 S1 117.9(3) . . ?
C11 C9 S1 118.9(3) . . ?
C7 C8 C3 122.2(4) . . ?
N2 C15 C11 124.2(4) . . ?
C5 C4 C3 122.7(4) . . ?
C5 C4 Br1 117.4(3) . . ?
C3 C4 Br1 119.8(3) . . ?
C12 C13 C14 118.9(4) . . ?
N2 C14 C13 123.5(4) . . ?
C13 C12 C11 119.3(4) . . ?
N1 C1 C2 178.1(5) . . ?
F1 C6 C5 117.2(4) . . ?
F1 C6 C7 119.4(4) . . ?
C5 C6 C7 123.4(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.895(4) . ?
S1 C9 1.762(4) . ?
S1 C10 1.802(5) . ?
F1 C6 1.359(5) . ?
N2 C14 1.330(6) . ?
N2 C15 1.340(6) . ?
C3 C4 1.395(6) . ?
C3 C8 1.399(6) . ?
C3 C2 1.494(6) . ?
C2 C9 1.362(6) . ?
C2 C1 1.447(6) . ?
N1 C1 1.148(6) . ?
C11 C15 1.397(6) . ?
C11 C12 1.402(6) . ?
C11 C9 1.469(6) . ?
C7 C6 1.377(6) . ?
C7 C8 1.385(6) . ?
C5 C6 1.375(6) . ?
C5 C4 1.388(6) . ?
C13 C12 1.372(6) . ?
C13 C14 1.392(6) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C3 C2 C9 129.3(5) . . . . ?
C8 C3 C2 C9 -55.5(6) . . . . ?
C4 C3 C2 C1 -57.2(6) . . . . ?
C8 C3 C2 C1 118.0(5) . . . . ?
C1 C2 C9 C11 174.4(4) . . . . ?
C3 C2 C9 C11 -12.3(7) . . . . ?
C1 C2 C9 S1 -8.1(6) . . . . ?
C3 C2 C9 S1 165.2(3) . . . . ?
C15 C11 C9 C2 -47.4(6) . . . . ?
C12 C11 C9 C2 135.8(5) . . . . ?
C15 C11 C9 S1 135.1(4) . . . . ?
C12 C11 C9 S1 -41.6(6) . . . . ?
C10 S1 C9 C2 145.2(4) . . . . ?
C10 S1 C9 C11 -37.2(4) . . . . ?
C6 C7 C8 C3 -0.2(7) . . . . ?
C4 C3 C8 C7 1.2(6) . . . . ?
C2 C3 C8 C7 -174.2(4) . . . . ?
C14 N2 C15 C11 1.4(6) . . . . ?
C12 C11 C15 N2 -2.2(6) . . . . ?
C9 C11 C15 N2 -179.1(4) . . . . ?
C6 C5 C4 C3 1.7(7) . . . . ?
C6 C5 C4 Br1 -175.1(3) . . . . ?
C8 C3 C4 C5 -2.0(6) . . . . ?
C2 C3 C4 C5 173.3(4) . . . . ?
C8 C3 C4 Br1 174.7(3) . . . . ?
C2 C3 C4 Br1 -9.9(6) . . . . ?
C15 N2 C14 C13 0.2(6) . . . . ?
C12 C13 C14 N2 -1.0(7) . . . . ?
C14 C13 C12 C11 0.1(7) . . . . ?
C15 C11 C12 C13 1.3(6) . . . . ?
C9 C11 C12 C13 178.1(4) . . . . ?
C9 C2 C1 N1 -140(14) . . . . ?
C3 C2 C1 N1 46(15) . . . . ?
C4 C5 C6 F1 -179.1(4) . . . . ?
C4 C5 C6 C7 -0.6(7) . . . . ?
C8 C7 C6 F1 178.3(4) . . . . ?
C8 C7 C6 C5 -0.1(7) . . . . ?
