#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/11/2221113.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_2221113
loop_
_publ_author_name
'Koch, Pierre'
'Schollmeyer, Dieter'
'Laufer, Stefan'
_publ_section_title
;
 4-[5-(4-Fluorophenyl)-1H-imidazol-4-yl]pyridine
;
_journal_coeditor_code           IM2099
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o573
_journal_paper_doi               10.1107/S1600536809005650
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H10 F N3'
_chemical_formula_moiety         'C14 H10 F N3'
_chemical_formula_sum            'C14 H10 F N3'
_chemical_formula_weight         239.25
_chemical_melting_point          285.5
_chemical_name_systematic
;
4-[5-(4-Fluorophenyl)-1H-imidazol-4-yl]pyridine
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.217(2)
_cell_length_b                   8.1064(5)
_cell_length_c                   30.665(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53
_cell_measurement_theta_min      31
_cell_volume                     2291.2(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CORINC (Dräger & Gattow, 1971)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       κ-geometry
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            2121
_diffrn_reflns_theta_full        69.58
_diffrn_reflns_theta_max         69.58
_diffrn_reflns_theta_min         2.88
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.539
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0764
_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)+(0.1422P)²+0.0554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1891
_refine_ls_wR_factor_ref         0.2010
_reflns_number_gt                1707
_reflns_number_total             2121
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2099.cif
_cod_data_source_block           I
_cod_original_cell_volume        2291.1(6)
_cod_database_code               2221113
_cod_database_fobs_code          2221113
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.0873(2) 0.0708(3) 0.21998(6) 0.0596(6) Uani d . 1 . .
N N1 -0.0150(2) 0.2988(2) 0.42177(7) 0.0243(5) Uani d . 1 . .
H H1 -0.1070 0.2883 0.4130 0.029 Uiso d R 1 . .
C C2 0.1085(2) 0.2755(3) 0.39720(8) 0.0224(5) Uani d . 1 . .
C C3 0.2212(3) 0.3123(3) 0.42585(8) 0.0227(5) Uani d . 1 . .
N N4 0.1672(2) 0.3595(3) 0.46674(7) 0.0285(5) Uani d . 1 . .
C C5 0.0257(3) 0.3479(3) 0.46279(9) 0.0279(6) Uani d . 1 . .
H H5 -0.0408 0.3708 0.4857 0.033 Uiso calc R 1 . .
C C6 0.1015(2) 0.2250(3) 0.35030(8) 0.0228(5) Uani d . 1 . .
C C7 0.1984(3) 0.2872(3) 0.31898(9) 0.0286(6) Uani d . 1 . .
H H7 0.2682 0.3669 0.3277 0.034 Uiso calc R 1 . .
C C8 0.1955(3) 0.2353(3) 0.27519(9) 0.0338(6) Uani d . 1 . .
H H8 0.2639 0.2764 0.2547 0.041 Uiso calc R 1 . .
C C9 0.0907(3) 0.1233(3) 0.26276(9) 0.0365(7) Uani d . 1 . .
C C10 -0.0096(3) 0.0625(3) 0.29215(9) 0.0353(6) Uani d . 1 . .
H H10 -0.0819 -0.0131 0.2828 0.042 Uiso calc R 1 . .
C C11 -0.0043(3) 0.1128(3) 0.33599(8) 0.0274(6) Uani d . 1 . .
H H11 -0.0731 0.0705 0.3562 0.033 Uiso calc R 1 . .
C C12 0.3785(3) 0.3036(3) 0.41935(8) 0.0216(5) Uani d . 1 . .
C C13 0.4700(3) 0.4057(3) 0.44398(8) 0.0246(5) Uani d . 1 . .
H H13 0.4299 0.4814 0.4643 0.030 Uiso calc R 1 . .
C C14 0.6182(3) 0.3961(3) 0.43855(8) 0.0282(6) Uani d . 1 . .
H H14 0.6783 0.4650 0.4559 0.034 Uiso calc R 1 . .
N N15 0.6824(2) 0.2927(3) 0.40951(7) 0.0287(5) Uani d . 1 . .
C C16 0.5937(3) 0.1937(3) 0.38606(9) 0.0290(6) Uani d . 1 . .
H H16 0.6367 0.1193 0.3659 0.035 Uiso calc R 1 . .
C C17 0.4456(3) 0.1942(3) 0.38966(8) 0.0264(6) Uani d . 1 . .
H H17 0.3885 0.1218 0.3724 0.032 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C2 . . 108.4(2) ?
C5 N1 H1 . . 124.3 ?
C2 N1 H1 . . 127.3 ?
N1 C2 C3 . . 104.0(2) ?
N1 C2 C6 . . 121.9(2) ?
C3 C2 C6 . . 134.2(2) ?
C2 C3 N4 . . 111.0(2) ?
C2 C3 C12 . . 129.9(2) ?
N4 C3 C12 . . 119.0(2) ?
C5 N4 C3 . . 104.5(2) ?
N4 C5 N1 . . 112.1(2) ?
N4 C5 H5 . . 123.9 ?
N1 C5 H5 . . 123.9 ?
C11 C6 C7 . . 117.4(2) ?
C11 C6 C2 . . 120.5(2) ?
C7 C6 C2 . . 122.1(2) ?
C6 C7 C8 . . 122.2(2) ?
C6 C7 H7 . . 118.9 ?
C8 C7 H7 . . 118.9 ?
C9 C8 C7 . . 118.3(3) ?
C9 C8 H8 . . 120.9 ?
C7 C8 H8 . . 120.9 ?
C8 C9 F1 . . 118.8(3) ?
C8 C9 C10 . . 121.5(3) ?
F1 C9 C10 . . 119.7(3) ?
C9 C10 C11 . . 119.8(2) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
C6 C11 C10 . . 120.7(2) ?
C6 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C13 C12 C17 . . 117.0(2) ?
C13 C12 C3 . . 119.6(2) ?
C17 C12 C3 . . 123.4(2) ?
C14 C13 C12 . . 119.8(2) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
N15 C14 C13 . . 123.1(2) ?
N15 C14 H14 . . 118.5 ?
C13 C14 H14 . . 118.5 ?
C16 N15 C14 . . 116.8(2) ?
N15 C16 C17 . . 123.9(2) ?
N15 C16 H16 . . 118.0 ?
C17 C16 H16 . . 118.0 ?
C16 C17 C12 . . 119.3(2) ?
C16 C17 H17 . . 120.3 ?
C12 C17 H17 . . 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C9 . 1.380(3) ?
N1 C5 . 1.372(3) ?
N1 C2 . 1.378(3) ?
N1 H1 . 0.8936 ?
C2 C3 . 1.393(3) ?
C2 C6 . 1.496(3) ?
C3 N4 . 1.402(3) ?
C3 C12 . 1.465(3) ?
N4 C5 . 1.313(3) ?
C5 H5 . 0.9500 ?
C6 C11 . 1.403(3) ?
C6 C7 . 1.405(3) ?
C7 C8 . 1.407(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.379(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.382(4) ?
C10 C11 . 1.406(4) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 C13 . 1.402(3) ?
C12 C17 . 1.414(3) ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.9500 ?
C14 N15 . 1.359(3) ?
C14 H14 . 0.9500 ?
N15 C16 . 1.353(3) ?
C16 C17 . 1.370(3) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 N15 1_455 0.89 1.94 2.815(3) 164
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 C3 . . . . 0.3(2) ?
C5 N1 C2 C6 . . . . -178.6(2) ?
N1 C2 C3 N4 . . . . -0.9(2) ?
C6 C2 C3 N4 . . . . 177.8(2) ?
N1 C2 C3 C12 . . . . 177.2(2) ?
C6 C2 C3 C12 . . . . -4.1(4) ?
C2 C3 N4 C5 . . . . 1.2(2) ?
C12 C3 N4 C5 . . . . -177.14(19) ?
C3 N4 C5 N1 . . . . -1.0(3) ?
C2 N1 C5 N4 . . . . 0.4(3) ?
N1 C2 C6 C11 . . . . -37.4(3) ?
C3 C2 C6 C11 . . . . 144.1(2) ?
N1 C2 C6 C7 . . . . 142.3(2) ?
C3 C2 C6 C7 . . . . -36.3(4) ?
C11 C6 C7 C8 . . . . -2.7(3) ?
C2 C6 C7 C8 . . . . 177.6(2) ?
C6 C7 C8 C9 . . . . 2.0(4) ?
C7 C8 C9 F1 . . . . -179.6(2) ?
C7 C8 C9 C10 . . . . 0.0(4) ?
C8 C9 C10 C11 . . . . -1.1(4) ?
F1 C9 C10 C11 . . . . 178.5(2) ?
C7 C6 C11 C10 . . . . 1.6(3) ?
C2 C6 C11 C10 . . . . -178.8(2) ?
C9 C10 C11 C6 . . . . 0.2(4) ?
C2 C3 C12 C13 . . . . 153.7(2) ?
N4 C3 C12 C13 . . . . -28.4(3) ?
C2 C3 C12 C17 . . . . -27.5(4) ?
N4 C3 C12 C17 . . . . 150.5(2) ?
C17 C12 C13 C14 . . . . 0.0(3) ?
C3 C12 C13 C14 . . . . 178.9(2) ?
C12 C13 C14 N15 . . . . 1.1(4) ?
C13 C14 N15 C16 . . . . -1.5(4) ?
C14 N15 C16 C17 . . . . 0.9(4) ?
N15 C16 C17 C12 . . . . 0.1(4) ?
C13 C12 C17 C16 . . . . -0.5(3) ?
C3 C12 C17 C16 . . . . -179.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 580940
