#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/54/2235463.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2235463
loop_
_publ_author_name
'Elahi, Fazal'
'Adeel, Muhammad'
'Tahir, M. Nawaz'
'Langer, Peter'
'Ahmad, Saeed'
_publ_section_title
;
 2-Fluoro-5-(4-fluorophenyl)pyridine
;
_journal_coeditor_code           HB6833
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2070
_journal_paper_doi               10.1107/S1600536812025160
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H7 F2 N'
_chemical_formula_moiety         'C11 H7 F2 N'
_chemical_formula_sum            'C11 H7 F2 N'
_chemical_formula_weight         191.18
_chemical_name_systematic
;
2-Fluoro-5-(4-fluorophenyl)pyridine
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.365(2)
_cell_length_b                   3.8303(3)
_cell_length_c                   11.4835(14)
_cell_measurement_reflns_used    1162
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.00
_cell_volume                     895.76(16)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.10
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3601
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.086
_refine_ls_abs_structure_details none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1489
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0299
_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/[σ²(Fo²)+(0.0344P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                1162
_reflns_number_total             1489
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6833.cif
_cod_data_source_block           I
_cod_original_cell_volume        895.74(16)
_cod_database_code               2235463
_cod_database_fobs_code          2235463
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,y,1/2+z
4 1/2+x,-y,z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
F F1 0.16885(7) -0.0787(5) 0.32200(16) 0.1219(8) Uani 1.000 -16
F F2 0.60621(6) 0.4445(4) 0.58901(13) 0.0984(6) Uani 1.000 -16
N N1 0.50519(9) 0.2455(5) 0.62465(14) 0.0695(7) Uani 1.000 -16
C C1 0.35628(9) 0.1391(5) 0.43374(16) 0.0497(7) Uani 1.000 -16
C C2 0.30232(10) 0.2088(6) 0.50519(18) 0.0635(9) Uani 1.000 -16
C C3 0.23904(11) 0.1346(7) 0.4674(2) 0.0767(10) Uani 1.000 -16
C C4 0.23116(11) -0.0048(7) 0.3597(2) 0.0785(11) Uani 1.000 -16
C C5 0.28211(11) -0.0803(6) 0.28686(19) 0.0713(9) Uani 1.000 -16
C C6 0.34494(10) -0.0045(5) 0.32527(18) 0.0586(8) Uani 1.000 -16
C C7 0.42374(9) 0.2219(5) 0.47208(15) 0.0468(7) Uani 1.000 -16
C C8 0.47047(9) 0.3501(6) 0.39465(17) 0.0560(8) Uani 1.000 -16
C C9 0.53273(10) 0.4268(5) 0.43285(19) 0.0609(8) Uani 1.000 -16
C C10 0.54517(11) 0.3685(6) 0.54736(19) 0.0636(9) Uani 1.000 -16
C C11 0.44444(10) 0.1735(5) 0.58562(18) 0.0603(8) Uani 1.000 -16
H H2 0.30881 0.30545 0.57858 0.0761 Uiso 1.000 -16
H H3 0.20297 0.17943 0.51471 0.0918 Uiso 1.000 -16
H H5 0.27490 -0.17911 0.21400 0.0855 Uiso 1.000 -16
H H6 0.38044 -0.05144 0.27678 0.0703 Uiso 1.000 -16
H H8 0.45950 0.38384 0.31684 0.0672 Uiso 1.000 -16
H H9 0.56470 0.51406 0.38289 0.0731 Uiso 1.000 -16
H H11 0.41423 0.08497 0.63868 0.0723 Uiso 1.000 -16
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C10 N1 C11 115.17(18) no
C2 C1 C6 118.31(18) no
C2 C1 C7 121.03(17) no
C6 C1 C7 120.66(17) no
C1 C2 C3 120.47(19) no
C2 C3 C4 118.4(2) no
F1 C4 C3 118.6(2) no
F1 C4 C5 117.8(2) no
C3 C4 C5 123.6(2) no
C4 C5 C6 117.6(2) no
C1 C6 C5 121.70(19) no
C1 C7 C8 121.42(16) no
C1 C7 C11 122.40(17) no
C8 C7 C11 116.18(17) no
C7 C8 C9 120.17(18) no
C8 C9 C10 116.52(19) no
F2 C10 N1 114.27(19) no
F2 C10 C9 118.35(19) no
N1 C10 C9 127.4(2) no
N1 C11 C7 124.57(18) no
C1 C2 H2 120.00 no
C3 C2 H2 120.00 no
C2 C3 H3 121.00 no
C4 C3 H3 121.00 no
C4 C5 H5 121.00 no
C6 C5 H5 121.00 no
C1 C6 H6 119.00 no
C5 C6 H6 119.00 no
C7 C8 H8 120.00 no
C9 C8 H8 120.00 no
C8 C9 H9 122.00 no
C10 C9 H9 122.00 no
N1 C11 H11 118.00 no
C7 C11 H11 118.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C4 1.370(3) no
F2 C10 1.363(3) no
N1 C10 1.293(3) no
N1 C11 1.344(3) no
C1 C2 1.397(3) no
C1 C6 1.381(3) no
C1 C7 1.477(3) no
C2 C3 1.389(3) no
C3 C4 1.357(3) no
C4 C5 1.364(3) no
C5 C6 1.384(3) no
C7 C8 1.392(3) no
C7 C11 1.383(3) no
C8 C9 1.374(3) no
C9 C10 1.358(3) no
C2 H2 0.9300 no
C3 H3 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C8 H8 0.9300 no
C9 H9 0.9300 no
C11 H11 0.9300 no
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_publ_flag
C11 N1 C10 F2 179.11(18) no
C11 N1 C10 C9 -1.0(3) no
C10 N1 C11 C7 0.1(3) no
C6 C1 C2 C3 0.0(3) no
C7 C1 C2 C3 179.0(2) no
C2 C1 C6 C5 -0.2(3) no
C7 C1 C6 C5 -179.19(19) no
C2 C1 C7 C8 -142.1(2) no
C2 C1 C7 C11 38.7(3) no
C6 C1 C7 C8 36.9(3) no
C6 C1 C7 C11 -142.3(2) no
C1 C2 C3 C4 -0.3(4) no
C2 C3 C4 F1 180.0(2) no
C2 C3 C4 C5 0.8(4) no
F1 C4 C5 C6 179.9(2) no
C3 C4 C5 C6 -1.0(4) no
C4 C5 C6 C1 0.7(3) no
C1 C7 C8 C9 179.62(19) no
C11 C7 C8 C9 -1.1(3) no
C1 C7 C11 N1 -179.87(18) no
C8 C7 C11 N1 0.9(3) no
C7 C8 C9 C10 0.4(3) no
C8 C9 C10 F2 -179.37(19) no
C8 C9 C10 N1 0.7(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23357348
