#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/54/2235475.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_2235475
loop_
_publ_author_name
'Elahi, Fazal'
'Adeel, Muhammad'
'Tahir, M. Nawaz'
_publ_section_title
;
 4-(2-Fluoropyridin-5-yl)phenol
;
_journal_coeditor_code           HB6846
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2124
_journal_paper_doi               10.1107/S1600536812026499
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H8 F N O'
_chemical_formula_moiety         'C11 H8 F N O'
_chemical_formula_sum            'C11 H8 F N O'
_chemical_formula_weight         189.18
_chemical_name_systematic
;
4-(2-Fluoropyridin-5-yl)phenol
;
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.275(3)
_cell_length_b                   7.4343(11)
_cell_length_c                   19.328(3)
_cell_measurement_reflns_used    869
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.11
_cell_volume                     1763.8(6)
_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 8.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0636
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7508
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.11
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.179
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0512
_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)+(0.0483P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                896
_reflns_number_total             1732
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6846.cif
_cod_data_source_block           I
_cod_database_code               2235475
_cod_database_fobs_code          2235475
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+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 0.16138(14) 0.0574(2) 0.57218(6) 0.0807(7) Uani 1.000 -16
O O1 0.44529(15) 0.4234(3) 0.12632(8) 0.0611(8) Uani 1.000 -16
N N1 0.3071(2) 0.1137(3) 0.50603(9) 0.0532(9) Uani 1.000 -16
C C1 0.3319(2) 0.2565(3) 0.31870(11) 0.0361(9) Uani 1.000 -16
C C2 0.4308(2) 0.3444(3) 0.31099(12) 0.0414(9) Uani 1.000 -16
C C3 0.4687(2) 0.3971(3) 0.24670(12) 0.0439(10) Uani 1.000 -16
C C4 0.4071(2) 0.3622(3) 0.18829(12) 0.0416(9) Uani 1.000 -16
C C5 0.3108(2) 0.2682(3) 0.19463(11) 0.0449(10) Uani 1.000 -16
C C6 0.2736(2) 0.2170(3) 0.25895(10) 0.0419(9) Uani 1.000 -16
C C7 0.2856(2) 0.2081(3) 0.38699(11) 0.0367(9) Uani 1.000 -16
C C8 0.1738(2) 0.2085(3) 0.39711(12) 0.0462(10) Uani 1.000 -16
C C9 0.1293(2) 0.1575(3) 0.45939(12) 0.0520(11) Uani 1.000 -16
C C10 0.2008(3) 0.1116(3) 0.51007(12) 0.0524(10) Uani 1.000 -16
C C11 0.3492(2) 0.1610(3) 0.44353(11) 0.0470(10) Uani 1.000 -16
H H1 0.39877 0.40831 0.09643 0.0916 Uiso 1.000 -16
H H2 0.47273 0.36848 0.34999 0.0497 Uiso 1.000 -16
H H3 0.53530 0.45572 0.24276 0.0527 Uiso 1.000 -16
H H5 0.27072 0.23925 0.15533 0.0540 Uiso 1.000 -16
H H6 0.20815 0.15470 0.26247 0.0503 Uiso 1.000 -16
H H8 0.12817 0.24378 0.36118 0.0555 Uiso 1.000 -16
H H9 0.05436 0.15458 0.46643 0.0624 Uiso 1.000 -16
H H11 0.42453 0.16170 0.43841 0.0565 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'
O O 0.0106 0.0060 '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
C4 O1 H1 109.00 no
C10 N1 C11 115.8(2) no
C2 C1 C6 117.5(2) no
C6 C1 C7 119.4(2) no
C2 C1 C7 123.1(2) no
C1 C2 C3 121.6(2) no
C2 C3 C4 119.7(2) no
O1 C4 C5 122.8(2) no
C3 C4 C5 119.4(2) no
O1 C4 C3 117.8(2) no
C4 C5 C6 120.3(2) no
C1 C6 C5 121.4(2) no
C1 C7 C8 120.3(2) no
C1 C7 C11 123.2(2) no
C8 C7 C11 116.5(2) no
C7 C8 C9 121.1(2) no
C8 C9 C10 116.3(2) no
F1 C10 N1 114.4(2) no
N1 C10 C9 126.8(2) no
F1 C10 C9 118.9(3) no
N1 C11 C7 123.4(2) no
C1 C2 H2 119.00 no
C3 C2 H2 119.00 no
C2 C3 H3 120.00 no
C4 C3 H3 120.00 no
C4 C5 H5 120.00 no
C6 C5 H5 120.00 no
C1 C6 H6 119.00 no
C5 C6 H6 119.00 no
C7 C8 H8 119.00 no
C9 C8 H8 119.00 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 C10 1.356(3) no
O1 C4 1.364(3) no
O1 H1 0.8200 no
N1 C11 1.360(3) no
N1 C10 1.307(4) no
C1 C2 1.387(3) no
C1 C7 1.481(3) no
C1 C6 1.390(3) no
C2 C3 1.384(3) no
C3 C4 1.383(3) no
C4 C5 1.379(3) no
C5 C6 1.378(3) no
C7 C8 1.386(3) no
C7 C11 1.388(3) no
C8 C9 1.375(3) no
C9 C10 1.359(4) 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_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
_geom_hbond_publ_flag
O1 H1 N1 8_554 0.82 2.08 2.891(3) 168 yes
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 F1 177.63(19) no
C11 N1 C10 C9 -2.5(4) no
C10 N1 C11 C7 1.2(3) no
C6 C1 C2 C3 2.3(3) no
C7 C1 C2 C3 -176.1(2) no
C2 C1 C6 C5 -2.0(3) no
C7 C1 C6 C5 176.5(2) no
C2 C1 C7 C8 146.8(2) no
C2 C1 C7 C11 -33.1(3) no
C6 C1 C7 C8 -31.6(3) no
C6 C1 C7 C11 148.5(2) no
C1 C2 C3 C4 0.1(3) no
C2 C3 C4 O1 177.2(2) no
C2 C3 C4 C5 -2.8(3) no
O1 C4 C5 C6 -176.9(2) no
C3 C4 C5 C6 3.1(3) no
C4 C5 C6 C1 -0.7(4) no
C1 C7 C8 C9 177.6(2) no
C11 C7 C8 C9 -2.6(3) no
C1 C7 C11 N1 -178.9(2) no
C8 C7 C11 N1 1.2(3) no
C7 C8 C9 C10 1.5(3) no
C8 C9 C10 F1 -178.9(2) no
C8 C9 C10 N1 1.2(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657877
