#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/10/2221000.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_2221000
loop_
_publ_author_name
'Abu Thaher, Bassam'
'Koch, Pierre'
'Schollmeyer, Dieter'
'Laufer, Stefan'
_publ_section_title
;
 4-[2-(4-Fluorophenyl)-1H-pyrrol-3-yl]pyridine
;
_journal_coeditor_code           BT2858
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o457
_journal_paper_doi               10.1107/S160053680900364X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H11 F N2'
_chemical_formula_moiety         'C15 H11 F N2'
_chemical_formula_sum            'C15 H11 F N2'
_chemical_formula_weight         238.26
_chemical_name_systematic
;
4-[2-(4-Fluorophenyl)-1H-pyrrol-3-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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.2966(7)
_cell_length_b                   8.1966(5)
_cell_length_c                   30.5738(19)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      51.7
_cell_measurement_theta_min      30
_cell_volume                     2329.7(3)
_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, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_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    0.0305
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            2175
_diffrn_reflns_theta_full        69.49
_diffrn_reflns_theta_max         69.49
_diffrn_reflns_theta_min         2.89
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.173
_refine_ls_extinction_coef       0.00086(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0415
_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)+(0.0641P)²+0.5148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1108
_refine_ls_wR_factor_ref         0.1199
_reflns_number_gt                1744
_reflns_number_total             2175
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2858.cif
_cod_data_source_block           I
_cod_database_code               2221000
_cod_database_fobs_code          2221000
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
N N1 0.51524(14) 0.21406(17) 0.41905(5) 0.0278(3) Uani d . 1 . .
H H1 0.6083 0.2266 0.4081 0.033 Uiso d R 1 . .
C C2 0.39066(16) 0.2347(2) 0.39570(6) 0.0249(4) Uani d . 1 . .
C C3 0.27690(16) 0.2008(2) 0.42407(5) 0.0255(4) Uani d . 1 . .
C C4 0.33869(18) 0.1586(2) 0.46491(6) 0.0311(4) Uani d . 1 . .
H H4 0.2876 0.1288 0.4906 0.037 Uiso calc R 1 . .
C C5 0.48474(18) 0.1684(2) 0.46075(6) 0.0317(4) Uani d . 1 . .
H H5 0.5531 0.1470 0.4831 0.038 Uiso calc R 1 . .
C C6 0.39610(16) 0.2800(2) 0.34938(5) 0.0264(4) Uani d . 1 . .
C C7 0.50091(18) 0.3890(2) 0.33407(6) 0.0331(4) Uani d . 1 . .
H H7 0.5698 0.4322 0.3539 0.040 Uiso calc R 1 . .
C C8 0.5055(2) 0.4345(3) 0.29053(6) 0.0421(5) Uani d . 1 . .
H H8 0.5773 0.5075 0.2802 0.051 Uiso calc R 1 . .
C C9 0.4047(2) 0.3721(3) 0.26266(6) 0.0429(5) Uani d . 1 . .
C C10 0.3009(2) 0.2630(3) 0.27593(6) 0.0395(5) Uani d . 1 . .
H H10 0.2329 0.2207 0.2557 0.047 Uiso calc R 1 . .
C C11 0.29785(18) 0.2163(2) 0.31936(6) 0.0311(4) Uani d . 1 . .
H H11 0.2279 0.1397 0.3289 0.037 Uiso calc R 1 . .
F F12 0.40632(16) 0.4201(2) 0.22006(4) 0.0706(5) Uani d . 1 . .
C C13 0.12145(16) 0.20955(19) 0.41599(5) 0.0244(4) Uani d . 1 . .
C C14 0.05747(18) 0.3235(2) 0.38834(6) 0.0292(4) Uani d . 1 . .
H H14 0.1155 0.3991 0.3727 0.035 Uiso calc R 1 . .
C C15 -0.09026(18) 0.3267(2) 0.38362(6) 0.0318(4) Uani d . 1 . .
H H15 -0.1307 0.4053 0.3644 0.038 Uiso calc R 1 . .
N N16 -0.17994(14) 0.2253(2) 0.40458(5) 0.0329(4) Uani d . 1 . .
C C17 -0.11823(18) 0.1169(2) 0.43157(6) 0.0320(4) Uani d . 1 . .
H H17 -0.1791 0.0442 0.4472 0.038 Uiso calc R 1 . .
C C18 0.02834(17) 0.1046(2) 0.43807(5) 0.0286(4) Uani d . 1 . .
H H18 0.0657 0.0248 0.4575 0.034 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'
F F 0.0727 0.0534 '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'
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 . . 110.27(14) ?
C5 N1 H1 . . 124.1 ?
C2 N1 H1 . . 125.6 ?
N1 C2 C3 . . 106.96(15) ?
N1 C2 C6 . . 120.37(14) ?
C3 C2 C6 . . 132.65(15) ?
C2 C3 C4 . . 106.80(14) ?
C2 C3 C13 . . 129.17(15) ?
C4 C3 C13 . . 124.00(15) ?
C5 C4 C3 . . 107.84(15) ?
C5 C4 H4 . . 126.1 ?
C3 C4 H4 . . 126.1 ?
N1 C5 C4 . . 108.13(15) ?
N1 C5 H5 . . 125.9 ?
C4 C5 H5 . . 125.9 ?
C11 C6 C7 . . 118.26(16) ?
C11 C6 C2 . . 121.19(15) ?
C7 C6 C2 . . 120.55(15) ?
C8 C7 C6 . . 120.96(18) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C9 C8 C7 . . 118.57(18) ?
C9 C8 H8 . . 120.7 ?
C7 C8 H8 . . 120.7 ?
F12 C9 C8 . . 118.76(19) ?
F12 C9 C10 . . 118.54(19) ?
C8 C9 C10 . . 122.70(18) ?
C9 C10 C11 . . 118.50(18) ?
C9 C10 H10 . . 120.8 ?
C11 C10 H10 . . 120.8 ?
C10 C11 C6 . . 120.97(17) ?
C10 C11 H11 . . 119.5 ?
C6 C11 H11 . . 119.5 ?
C14 C13 C18 . . 116.25(15) ?
C14 C13 C3 . . 123.73(15) ?
C18 C13 C3 . . 119.96(15) ?
C15 C14 C13 . . 120.04(16) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
N16 C15 C14 . . 123.85(17) ?
N16 C15 H15 . . 118.1 ?
C14 C15 H15 . . 118.1 ?
C15 N16 C17 . . 116.02(14) ?
N16 C17 C18 . . 123.98(16) ?
N16 C17 H17 . . 118.0 ?
C18 C17 H17 . . 118.0 ?
C17 C18 C13 . . 119.86(16) ?
C17 C18 H18 . . 120.1 ?
C13 C18 H18 . . 120.1 ?
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
N1 C5 . 1.358(2) ?
N1 C2 . 1.371(2) ?
N1 H1 . 0.9339 ?
C2 C3 . 1.396(2) ?
C2 C6 . 1.465(2) ?
C3 C4 . 1.417(2) ?
C3 C13 . 1.468(2) ?
C4 C5 . 1.366(2) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 C11 . 1.396(2) ?
C6 C7 . 1.402(2) ?
C7 C8 . 1.383(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.366(3) ?
C8 H8 . 0.9500 ?
C9 F12 . 1.360(2) ?
C9 C10 . 1.377(3) ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C13 C14 . 1.393(2) ?
C13 C18 . 1.395(2) ?
C14 C15 . 1.381(2) ?
C14 H14 . 0.9500 ?
C15 N16 . 1.340(2) ?
C15 H15 . 0.9500 ?
N16 C17 . 1.341(2) ?
C17 C18 . 1.381(2) ?
C17 H17 . 0.9500 ?
C18 H18 . 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 N16 1_655 0.93 1.97 2.8696(19) 160.8
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 . . . . 0.13(19) ?
C5 N1 C2 C6 . . . . -178.44(15) ?
N1 C2 C3 C4 . . . . -0.29(18) ?
C6 C2 C3 C4 . . . . 178.03(17) ?
N1 C2 C3 C13 . . . . 177.86(16) ?
C6 C2 C3 C13 . . . . -3.8(3) ?
C2 C3 C4 C5 . . . . 0.4(2) ?
C13 C3 C4 C5 . . . . -177.92(16) ?
C2 N1 C5 C4 . . . . 0.1(2) ?
C3 C4 C5 N1 . . . . -0.3(2) ?
N1 C2 C6 C11 . . . . 142.67(16) ?
C3 C2 C6 C11 . . . . -35.5(3) ?
N1 C2 C6 C7 . . . . -37.2(2) ?
C3 C2 C6 C7 . . . . 144.63(19) ?
C11 C6 C7 C8 . . . . 1.1(3) ?
C2 C6 C7 C8 . . . . -178.99(17) ?
C6 C7 C8 C9 . . . . 0.6(3) ?
C7 C8 C9 F12 . . . . 178.17(18) ?
C7 C8 C9 C10 . . . . -1.6(3) ?
F12 C9 C10 C11 . . . . -178.99(17) ?
C8 C9 C10 C11 . . . . 0.8(3) ?
C9 C10 C11 C6 . . . . 1.0(3) ?
C7 C6 C11 C10 . . . . -1.9(2) ?
C2 C6 C11 C10 . . . . 178.16(16) ?
C2 C3 C13 C14 . . . . -33.5(3) ?
C4 C3 C13 C14 . . . . 144.40(18) ?
C2 C3 C13 C18 . . . . 149.46(17) ?
C4 C3 C13 C18 . . . . -32.7(2) ?
C18 C13 C14 C15 . . . . -0.8(2) ?
C3 C13 C14 C15 . . . . -177.95(16) ?
C13 C14 C15 N16 . . . . 0.4(3) ?
C14 C15 N16 C17 . . . . 0.3(3) ?
C15 N16 C17 C18 . . . . -0.7(3) ?
N16 C17 C18 C13 . . . . 0.3(3) ?
C14 C13 C18 C17 . . . . 0.4(2) ?
C3 C13 C18 C17 . . . . 177.73(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10675526
