#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/72/2017204.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_2017204
loop_
_publ_author_name
'McMahon, Joyce'
'Gallagher, John F.'
'Anderson, Frankie P.'
'Lough, Alan J.'
_publ_section_title
;
 A structural systematic study of four isomers of
 difluoro-N-(3-pyridyl)benzamide
;
_journal_coeditor_code           SK3328
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o345
_journal_page_last               o351
_journal_paper_doi               10.1107/S010827010902215X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H8 F2 N2 O'
_chemical_formula_moiety         'C12 H8 F2 N2 O'
_chemical_formula_structural     'C12 H8 F2 N2 O'
_chemical_formula_sum            'C12 H8 F2 N2 O'
_chemical_formula_weight         234.20
_chemical_melting_point          437
_chemical_name_common            35m
_chemical_name_systematic
;
3,5-difluoro-N-(3-pyridyl)benzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 101.152(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3784(5)
_cell_length_b                   12.6278(8)
_cell_length_c                   9.9118(5)
_cell_measurement_reflns_used    3690
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.55
_cell_volume                     1028.87(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PREP8 (Ferguson, 1998)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ, ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7054
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.64
_diffrn_standards_number         2916
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.238
_refine_ls_extinction_coef       0.014(5)
_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   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0514
_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)+(0.0788P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                1535
_reflns_number_total             2348
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3328.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017204
_cod_database_fobs_code          2017204
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 F13 0.86046(14) 0.74307(9) 0.28043(13) 0.0497(4) Uani d . 1 . .
F F15 0.37984(14) 0.58544(9) 0.04623(11) 0.0440(4) Uani d . 1 . .
O O1 0.83831(15) 0.40070(10) 0.51724(13) 0.0339(4) Uani d . 1 . .
C C1 0.6993(2) 0.41253(13) 0.45201(18) 0.0255(4) Uani d . 1 . .
N N1 0.57409(19) 0.34999(12) 0.47156(15) 0.0261(4) Uani d . 1 . .
C C11 0.6629(2) 0.49972(13) 0.34788(17) 0.0256(4) Uani d . 1 . .
C C12 0.7771(2) 0.58133(13) 0.36008(19) 0.0285(4) Uani d . 1 . .
C C13 0.7509(2) 0.66224(14) 0.26618(19) 0.0327(5) Uani d . 1 . .
C C14 0.6196(2) 0.66677(15) 0.15852(19) 0.0320(5) Uani d . 1 . .
C C15 0.5111(2) 0.58467(15) 0.15042(18) 0.0302(5) Uani d . 1 . .
C C16 0.5279(2) 0.50121(14) 0.24170(18) 0.0285(4) Uani d . 1 . .
C C21 0.5861(2) 0.26335(14) 0.56326(17) 0.0258(4) Uani d . 1 . .
C C22 0.7137(2) 0.24926(14) 0.67524(18) 0.0295(4) Uani d . 1 . .
N N23 0.72100(19) 0.16792(12) 0.76305(15) 0.0330(4) Uani d . 1 . .
C C24 0.5983(2) 0.09807(15) 0.7421(2) 0.0339(5) Uani d . 1 . .
C C25 0.4674(2) 0.10642(16) 0.6348(2) 0.0366(5) Uani d . 1 . .
C C26 0.4613(2) 0.18984(15) 0.54430(19) 0.0317(5) Uani d . 1 . .
H H1 0.480(2) 0.3590(16) 0.415(2) 0.032(5) Uiso d . 1 . .
H H12 0.8706 0.5808 0.4317 0.034 Uiso calc R 1 . .
H H14 0.6052 0.7232 0.0940 0.038 Uiso calc R 1 . .
H H16 0.4493 0.4462 0.2322 0.034 Uiso calc R 1 . .
H H22 0.7994 0.2997 0.6899 0.035 Uiso calc R 1 . .
H H24 0.6019 0.0403 0.8039 0.041 Uiso calc R 1 . .
H H25 0.3825 0.0554 0.6234 0.044 Uiso calc R 1 . .
H H26 0.3720 0.1968 0.4695 0.038 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 122.36(16) ?
O1 C1 C11 . . 119.86(16) ?
N1 C1 C11 . . 117.77(16) ?
C1 N1 C21 . . 125.55(16) ?
C16 C11 C12 . . 120.00(17) ?
C16 C11 C1 . . 123.99(16) ?
C12 C11 C1 . . 115.98(16) ?
C13 C12 C11 . . 118.37(17) ?
F13 C13 C12 . . 118.20(17) ?
F13 C13 C14 . . 118.06(16) ?
C12 C13 C14 . . 123.74(17) ?
C15 C14 C13 . . 115.80(17) ?
F15 C15 C14 . . 118.06(16) ?
F15 C15 C16 . . 118.09(16) ?
C14 C15 C16 . . 123.85(17) ?
C15 C16 C11 . . 118.24(17) ?
C26 C21 C22 . . 117.71(16) ?
C26 C21 N1 . . 118.27(15) ?
C22 C21 N1 . . 123.97(16) ?
N23 C22 C21 . . 123.12(17) ?
C24 N23 C22 . . 117.80(16) ?
N23 C24 C25 . . 122.86(18) ?
C24 C25 C26 . . 119.03(18) ?
C25 C26 C21 . . 119.48(17) ?
C1 N1 H1 . . 117.0(13) ?
C21 N1 H1 . . 116.9(13) ?
C11 C12 H12 . . 120.8 ?
C13 C12 H12 . . 120.8 ?
C13 C14 H14 . . 122.1 ?
C15 C14 H14 . . 122.1 ?
C11 C16 H16 . . 120.9 ?
C15 C16 H16 . . 120.9 ?
C21 C22 H22 . . 118.4 ?
N23 C22 H22 . . 118.4 ?
N23 C24 H24 . . 118.6 ?
C25 C24 H24 . . 118.6 ?
C24 C25 H25 . . 120.5 ?
C26 C25 H25 . . 120.5 ?
C25 C26 H26 . . 120.3 ?
C21 C26 H26 . . 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
F13 C13 . 1.361(2) ?
F15 C15 . 1.355(2) ?
O1 C1 . 1.227(2) ?
C1 N1 . 1.357(2) ?
C1 C11 . 1.500(2) ?
N1 C21 . 1.413(2) ?
C11 C12 . 1.395(2) ?
C11 C16 . 1.388(2) ?
C12 C13 . 1.371(2) ?
C13 C14 . 1.378(3) ?
C14 C15 . 1.371(3) ?
C15 C16 . 1.378(3) ?
C21 C22 . 1.395(2) ?
C21 C26 . 1.384(2) ?
C22 N23 . 1.340(2) ?
N23 C24 . 1.340(2) ?
C24 C25 . 1.376(3) ?
C25 C26 . 1.378(3) ?
N1 H1 . 0.89(2) ?
C12 H12 . 0.9500 ?
C14 H14 . 0.9500 ?
C16 H16 . 0.9500 ?
C22 H22 . 0.9500 ?
C24 H24 . 0.9500 ?
C25 H25 . 0.9500 ?
C26 H26 . 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
_geom_hbond_publ_flag
N1 H1 N23 4_565 0.89(2) 2.41(2) 3.272(2) 164.5(18) yes
C22 H22 O1 . 0.95 2.21 2.799(2) 119 yes
C12 H12 O1 3_766 0.95 2.40 3.225(2) 144 yes
C16 H16 N23 4_565 0.95 2.46 3.381(2) 163 yes
C14 H14 O1 2_655 0.95 2.58 3.482(2) 158 yes
C24 H24 O1 2_646 0.95 2.48 3.420(2) 170 yes
C25 H25 F15 2_545 0.95 2.52 3.120(2) 121 yes
C26 H26 F15 2_545 0.95 2.52 3.117(2) 121 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 N1 C21 . . . . -2.1(3) no
C11 C1 N1 C21 . . . . 178.88(15) no
O1 C1 C11 C16 . . . . 159.62(16) ?
N1 C1 C11 C16 . . . . -21.3(2) ?
O1 C1 C11 C12 . . . . -18.6(2) no
N1 C1 C11 C12 . . . . 160.44(15) ?
C16 C11 C12 C13 . . . . 0.7(3) ?
C1 C11 C12 C13 . . . . 179.01(15) ?
C11 C12 C13 F13 . . . . 178.39(15) ?
C11 C12 C13 C14 . . . . -1.2(3) ?
F13 C13 C14 C15 . . . . -178.64(15) ?
C12 C13 C14 C15 . . . . 1.0(3) ?
C13 C14 C15 F15 . . . . -179.94(15) ?
C13 C14 C15 C16 . . . . -0.2(3) ?
F15 C15 C16 C11 . . . . 179.47(15) ?
C14 C15 C16 C11 . . . . -0.3(3) ?
C12 C11 C16 C15 . . . . 0.0(3) ?
C1 C11 C16 C15 . . . . -178.17(15) ?
C1 N1 C21 C26 . . . . -161.81(17) ?
C1 N1 C21 C22 . . . . 20.7(3) no
C26 C21 C22 N23 . . . . 0.8(3) ?
N1 C21 C22 N23 . . . . 178.32(15) ?
C21 C22 N23 C24 . . . . -0.8(3) ?
C22 N23 C24 C25 . . . . 0.3(3) ?
N23 C24 C25 C26 . . . . 0.2(3) ?
C24 C25 C26 C21 . . . . -0.2(3) ?
C22 C21 C26 C25 . . . . -0.3(3) ?
N1 C21 C26 C25 . . . . -177.94(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1831106
