#------------------------------------------------------------------------------
#$Date: 2019-07-11 07:09:03 +0300 (Thu, 11 Jul 2019) $
#$Revision: 216956 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/30/2243002.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_2243002
loop_
_publ_author_name
'Peloquin, Andrew J.'
'Corley, Cynthia A.'
'Adas, Sonya K.'
'Balaich, Gary J.'
'Iacono, Scott T.'
_publ_section_title
;
 Crystal structures and Hirshfeld surface analysis of a series of
 4-O-arylperfluoropyridines
;
_journal_coeditor_code           HB7833
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1102
_journal_page_last               1107
_journal_paper_doi               10.1107/S2056989019009344
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C11 H5 F4 N O'
_chemical_formula_moiety         'C11 H5 F4 N O'
_chemical_formula_sum            'C11 H5 F4 N O'
_chemical_formula_weight         243.16
_chemical_name_common            E27_Corley
_chemical_name_systematic
;
2,3,5,6-Tetrafluoro-4-phenoxypyridine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4199(5)
_cell_length_b                   10.3293(9)
_cell_length_c                   17.4076(15)
_cell_measurement_reflns_used    7895
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      29.5413
_cell_measurement_theta_min      2.2927
_cell_volume                     974.54(15)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
Olex2 (Dolomanov et al., 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'Omega Scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13236
_diffrn_reflns_theta_full        29.11
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         2.29
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.147
_refine_ls_abs_structure_details
;
Flack x determined using 1019 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.20(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0371P)²+0.2471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                2520
_reflns_number_total             2603
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7833sup1.cif
_cod_data_source_block           I
_cod_database_code               2243002
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
F F1 1.0458(2) 0.96948(10) 0.27358(6) 0.0304(2) Uani d 1
F F2 0.64334(19) 0.87849(9) 0.34737(5) 0.0247(2) Uani d 1
F F3 0.4522(2) 0.64159(11) 0.12257(6) 0.0339(3) Uani d 1
F F4 0.8628(2) 0.74537(11) 0.05818(6) 0.0354(3) Uani d 1
O O1 0.3304(2) 0.70337(11) 0.27133(6) 0.0220(2) Uani d 1
N N1 0.9535(3) 0.85667(14) 0.16598(8) 0.0232(3) Uani d 1
C C1 0.8951(3) 0.88735(15) 0.23682(9) 0.0214(3) Uani d 1
C C2 0.6915(3) 0.84050(14) 0.27546(8) 0.0185(3) Uani d 1
C C3 0.5371(3) 0.75320(15) 0.23844(9) 0.0182(3) Uani d 1
C C4 0.5954(3) 0.72270(15) 0.16263(9) 0.0223(3) Uani d 1
C C5 0.8047(3) 0.77713(16) 0.13038(9) 0.0240(3) Uani d 1
C C6 0.3557(3) 0.65167(14) 0.34628(8) 0.0179(3) Uani d 1
C C7 0.1718(3) 0.68151(16) 0.39875(9) 0.0212(3) Uani d 1
H H7 0.041504 0.738816 0.385477 0.025 Uiso calc 1
C C8 0.1829(3) 0.62530(16) 0.47149(9) 0.0227(3) Uani d 1
H H8 0.058655 0.644261 0.508309 0.027 Uiso calc 1
C C9 0.3749(3) 0.54150(15) 0.49061(9) 0.0214(3) Uani d 1
H H9 0.380741 0.503169 0.540181 0.026 Uiso calc 1
C C10 0.5583(3) 0.51402(15) 0.43697(9) 0.0210(3) Uani d 1
H H10 0.689859 0.4575 0.450189 0.025 Uiso calc 1
C C11 0.5492(3) 0.56943(15) 0.36367(9) 0.0194(3) Uani d 1
H H11 0.673132 0.550979 0.326676 0.023 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
O O 0.0106 0.0060 '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
C3 O1 C6 116.81(12)
C5 N1 C1 116.66(14)
N1 C1 F1 117.05(14)
N1 C1 C2 124.49(15)
F1 C1 C2 118.46(14)
F2 C2 C1 120.62(14)
F2 C2 C3 120.48(14)
C1 C2 C3 118.90(14)
O1 C3 C2 123.16(13)
O1 C3 C4 120.02(14)
C2 C3 C4 116.73(14)
F3 C4 C5 121.20(15)
F3 C4 C3 120.24(15)
C5 C4 C3 118.56(15)
N1 C5 F4 117.04(15)
N1 C5 C4 124.62(15)
F4 C5 C4 118.33(16)
C11 C6 C7 122.50(14)
C11 C6 O1 120.43(13)
C7 C6 O1 116.98(13)
C6 C7 C8 118.34(15)
C6 C7 H7 120.8
C8 C7 H7 120.8
C9 C8 C7 120.50(15)
C9 C8 H8 119.8
C7 C8 H8 119.8
C10 C9 C8 119.95(14)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C11 120.18(15)
C9 C10 H10 119.9
C11 C10 H10 119.9
C6 C11 C10 118.52(14)
C6 C11 H11 120.7
C10 C11 H11 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.3404(18)
F2 C2 1.3375(17)
F3 C4 1.3382(19)
F4 C5 1.3366(18)
O1 C3 1.3594(18)
O1 C6 1.4164(18)
N1 C5 1.307(2)
N1 C1 1.312(2)
C1 C2 1.380(2)
C2 C3 1.389(2)
C3 C4 1.393(2)
C4 C5 1.385(2)
C6 C11 1.383(2)
C6 C7 1.387(2)
C7 C8 1.394(2)
C7 H7 0.9500
C8 C9 1.394(2)
C8 H8 0.9500
C9 C10 1.393(2)
C9 H9 0.9500
C10 C11 1.399(2)
C10 H10 0.9500
C11 H11 0.9500
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
C5 N1 C1 F1 -179.60(14)
C5 N1 C1 C2 0.7(2)
N1 C1 C2 F2 -178.92(14)
F1 C1 C2 F2 1.4(2)
N1 C1 C2 C3 1.1(2)
F1 C1 C2 C3 -178.63(13)
C6 O1 C3 C2 -49.3(2)
C6 O1 C3 C4 134.31(15)
F2 C2 C3 O1 1.0(2)
C1 C2 C3 O1 -178.94(14)
F2 C2 C3 C4 177.58(14)
C1 C2 C3 C4 -2.4(2)
O1 C3 C4 F3 -1.8(2)
C2 C3 C4 F3 -178.48(14)
O1 C3 C4 C5 178.73(14)
C2 C3 C4 C5 2.1(2)
C1 N1 C5 F4 180.00(14)
C1 N1 C5 C4 -1.1(2)
F3 C4 C5 N1 -179.80(15)
C3 C4 C5 N1 -0.4(2)
F3 C4 C5 F4 -0.9(2)
C3 C4 C5 F4 178.56(14)
C3 O1 C6 C11 -46.61(19)
C3 O1 C6 C7 136.93(15)
C11 C6 C7 C8 -0.5(2)
O1 C6 C7 C8 175.90(14)
C6 C7 C8 C9 0.1(2)
C7 C8 C9 C10 0.4(2)
C8 C9 C10 C11 -0.6(2)
C7 C6 C11 C10 0.3(2)
O1 C6 C11 C10 -175.95(14)
C9 C10 C11 C6 0.2(2)

_cod_database_fobs_code 2243002
