#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/74/4507451.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_4507451
loop_
_publ_author_name
'Siram, Raja Bhaskar Kanth'
'Karothu, Durga Prasad'
'Guru Row, Tayur N.'
'Patil, Satish'
_publ_section_title
;
 Unique Type II Halogen···Halogen Interactions in
 Pentafluorophenyl-Appended 2,2′-Bithiazoles
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1045
_journal_paper_doi               10.1021/cg3012298
_journal_volume                  13
_journal_year                    2013
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C18 Br2 F10 N2 S2'
_chemical_formula_sum            'C18 Br2 F10 N2 S2'
_chemical_formula_weight         658.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 101.142(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9430(5)
_cell_length_b                   15.7223(7)
_cell_length_c                   6.2495(3)
_cell_measurement_reflns_used    16046
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.1
_cell_volume                     958.55(8)
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16046
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    4.554
_exptl_absorpt_correction_T_max  0.4628
_exptl_absorpt_correction_T_min  0.3420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.280
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.064
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.475
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.475
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0196
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0257P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0543
_reflns_number_gt                1961
_reflns_number_total             2081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3012298_si_003.cif
_cod_data_source_block           grk
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4507451
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
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
Br1 Br 1.085720(17) 1.188322(11) 1.14160(3) 0.02059(9) Uani 1 1 d
S2 S 0.93537(4) 1.07851(3) 0.75233(7) 0.01638(11) Uani 1 1 d
F1 F 1.75364(10) 1.14462(7) 1.17005(19) 0.0254(3) Uani 1 1 d
F2 F 1.58856(11) 1.07088(7) 1.41925(17) 0.0257(2) Uani 1 1 d
F4 F 1.37830(11) 1.17336(7) 0.59273(17) 0.0223(2) Uani 1 1 d
F3 F 1.64708(11) 1.19571(6) 0.7600(2) 0.0267(3) Uani 1 1 d
F5 F 1.32362(10) 1.04231(7) 1.24906(16) 0.0218(2) Uani 1 1 d
N1 N 1.16445(14) 1.03750(9) 0.6440(2) 0.0154(3) Uani 1 1 d
C1 C 1.42831(18) 1.14538(10) 0.7952(3) 0.0167(3) Uani 1 1 d
C2 C 1.34224(17) 1.10705(10) 0.9164(3) 0.0148(3) Uani 1 1 d
C3 C 1.56618(18) 1.15785(11) 0.8796(3) 0.0189(4) Uani 1 1 d
C4 C 1.62063(17) 1.13228(11) 1.0892(3) 0.0185(4) Uani 1 1 d
C5 C 1.53728(18) 1.09528(11) 1.2155(3) 0.0183(4) Uani 1 1 d
C6 C 1.40067(17) 1.08230(10) 1.1268(3) 0.0164(3) Uani 1 1 d
C7 C 1.08587(17) 1.11684(10) 0.9035(3) 0.0151(3) Uani 1 1 d
C8 C 1.19657(17) 1.08910(10) 0.8240(3) 0.0140(3) Uani 1 1 d
C9 C 1.03254(18) 1.02648(10) 0.5913(3) 0.0154(3) 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'
Br Br -0.2901 2.4595 ' 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'
N N 0.0061 0.0033 ' 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'
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
C7 S2 C9 87.76(8) . .
C9 N1 C8 110.48(14) . .
F4 C1 C3 118.19(16) . .
F4 C1 C2 120.19(15) . .
C3 C1 C2 121.60(17) . .
C1 C2 C6 116.78(15) . .
C1 C2 C8 122.09(16) . .
C6 C2 C8 121.06(15) . .
F3 C3 C4 119.50(16) . .
F3 C3 C1 120.52(16) . .
C4 C3 C1 119.97(16) . .
F1 C4 C3 119.75(16) . .
F1 C4 C5 120.34(17) . .
C3 C4 C5 119.90(16) . .
F2 C5 C4 120.47(16) . .
F2 C5 C6 120.44(16) . .
C4 C5 C6 119.08(17) . .
F5 C6 C5 117.87(15) . .
F5 C6 C2 119.47(15) . .
C5 C6 C2 122.64(16) . .
C8 C7 S2 111.46(12) . .
C8 C7 Br1 127.50(13) . .
S2 C7 Br1 121.04(9) . .
C7 C8 N1 114.27(15) . .
C7 C8 C2 126.51(15) . .
N1 C8 C2 119.19(14) . .
N1 C9 C9 123.20(19) . 3_776
N1 C9 S2 116.02(13) . .
C9 C9 S2 120.78(17) 3_776 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C7 1.8648(16) .
S2 C7 1.7172(17) .
S2 C9 1.7297(17) .
F1 C4 1.3356(19) .
F2 C5 1.333(2) .
F4 C1 1.341(2) .
F3 C3 1.3386(19) .
F5 C6 1.3388(19) .
N1 C9 1.301(2) .
N1 C8 1.373(2) .
C1 C3 1.384(2) .
C1 C2 1.386(2) .
C2 C6 1.387(2) .
C2 C8 1.479(2) .
C3 C4 1.377(3) .
C4 C5 1.379(3) .
C5 C6 1.380(2) .
C7 C8 1.364(2) .
C9 C9 1.459(3) 3_776
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_4
F4 C1 C2 C6 -177.97(14) .
C3 C1 C2 C6 0.4(2) .
F4 C1 C2 C8 5.0(2) .
C3 C1 C2 C8 -176.57(15) .
F4 C1 C3 F3 -1.0(2) .
C2 C1 C3 F3 -179.42(15) .
F4 C1 C3 C4 178.11(16) .
C2 C1 C3 C4 -0.3(3) .
F3 C3 C4 F1 -0.7(2) .
C1 C3 C4 F1 -179.85(15) .
F3 C3 C4 C5 178.27(15) .
C1 C3 C4 C5 -0.8(3) .
F1 C4 C5 F2 -0.5(3) .
C3 C4 C5 F2 -179.46(15) .
F1 C4 C5 C6 -179.17(15) .
C3 C4 C5 C6 1.8(3) .
F2 C5 C6 F5 -2.1(2) .
C4 C5 C6 F5 176.61(15) .
F2 C5 C6 C2 179.54(15) .
C4 C5 C6 C2 -1.8(3) .
C1 C2 C6 F5 -177.73(14) .
C8 C2 C6 F5 -0.7(2) .
C1 C2 C6 C5 0.6(2) .
C8 C2 C6 C5 177.64(15) .
C9 S2 C7 C8 0.39(13) .
C9 S2 C7 Br1 179.63(11) .
S2 C7 C8 N1 -0.08(19) .
Br1 C7 C8 N1 -179.26(12) .
S2 C7 C8 C2 -177.97(13) .
Br1 C7 C8 C2 2.9(3) .
C9 N1 C8 C7 -0.4(2) .
C9 N1 C8 C2 177.64(14) .
C1 C2 C8 C7 -123.05(19) .
C6 C2 C8 C7 60.1(2) .
C1 C2 C8 N1 59.2(2) .
C6 C2 C8 N1 -117.70(18) .
C8 N1 C9 C9 -178.99(19) 3_776
C8 N1 C9 S2 0.74(18) .
C7 S2 C9 N1 -0.67(14) .
C7 S2 C9 C9 179.07(19) 3_776
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102190038
