#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:27:03 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180435 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/04/7210456.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7210456
loop_
_publ_author_name
'Mocilac, Pavle'
'Lough, Alan J.'
'Gallagher, John F.'
_publ_section_title
;
 Structures and conformational analysis of a 3 x 3 isomer grid of nine
 N-(fluorophenyl)pyridinecarboxamides
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1899
_journal_paper_doi               10.1039/c0ce00326c
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C12 H8.97 Cl0.03 F N2 O'
_chemical_formula_sum            'C12 H8.97 Cl0.03 F N2 O'
_chemical_formula_weight         217.33
_chemical_melting_point          379
_chemical_name_common            NooF
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.276(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8030(4)
_cell_length_b                   19.1318(18)
_cell_length_c                   10.8759(8)
_cell_measurement_reflns_used    12678
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.55
_cell_volume                     986.32(14)
_computing_cell_refinement       'DENZO-SMN (Otwinowski and Minor, 1997)'
_computing_data_collection       'kappaCCD Server software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski and Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PREP8 (Ferguson, 1998)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0897
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6707
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.85
_diffrn_standards_number         6843
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             449.6
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0568
_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)+(0.0713P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1535
_reflns_number_gt                1160
_reflns_number_total             2238
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0ce00326c.txt
_cod_data_source_block           NooF_[8-14]
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7210456
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F12 F -0.0260(3) 0.16417(7) -0.06780(11) 0.0503(4) Uani 1 1 d . . .
O1 O -0.1037(4) 0.08145(8) 0.35051(13) 0.0507(5) Uani 1 1 d . . .
C1 C -0.0008(5) 0.06727(12) 0.2579(2) 0.0391(6) Uani 1 1 d . . .
N1 N -0.0569(4) 0.10146(10) 0.14724(17) 0.0417(5) Uani 1 1 d . . .
H1 H 0.046(5) 0.0834(12) 0.090(2) 0.050(7) Uiso 1 1 d . . .
C11 C -0.2233(5) 0.16107(11) 0.1164(2) 0.0386(6) Uani 1 1 d . . .
C12 C -0.2052(5) 0.19352(13) 0.0037(2) 0.0413(6) Uani 1 1 d . . .
C13 C -0.3520(5) 0.25245(13) -0.0371(2) 0.0455(6) Uani 1 1 d . . .
H13 H -0.3323 0.2730 -0.1148 0.055 Uiso 1 1 calc R . .
C14 C -0.5299(5) 0.28156(13) 0.0371(2) 0.0449(6) Uani 1 1 d . . .
H14 H -0.6342 0.3226 0.0107 0.054 Uiso 1 1 calc R . .
C15 C -0.5554(5) 0.25074(12) 0.14967(19) 0.0438(6) Uani 1 1 d . . .
H15 H -0.6781 0.2707 0.2004 0.053 Uiso 1 1 calc R . .
C16 C -0.4033(5) 0.19084(12) 0.1896(2) 0.0417(6) Uani 1 1 d . . .
H16 H -0.4227 0.1702 0.2672 0.050 Uiso 1 1 calc R . .
C21 C 0.2114(5) 0.00946(12) 0.25693(19) 0.0386(6) Uani 1 1 d . A .
N22 N 0.3157(4) 0.00048(10) 0.15019(15) 0.0424(5) Uani 1 1 d . . .
C23 C 0.5067(5) -0.04998(13) 0.1486(2) 0.0458(6) Uani 1 1 d . A .
H23 H 0.5818 -0.0573 0.0740 0.055 Uiso 1 1 calc R . .
C24 C 0.6013(5) -0.09229(12) 0.2503(2) 0.0454(6) Uani 1 1 d . . .
H24 H 0.7377 -0.1277 0.2453 0.054 Uiso 1 1 calc R A .
C25 C 0.4938(5) -0.08190(12) 0.3586(2) 0.0462(7) Uani 1 1 d . A -1
H25 H 0.5568 -0.1097 0.4300 0.055 Uiso 0.968(3) 1 calc PR B -1
C26 C 0.2930(5) -0.03060(13) 0.36250(19) 0.0435(6) Uani 1 1 d . . .
H26 H 0.2131 -0.0230 0.4358 0.052 Uiso 1 1 calc R A .
Cl25 Cl 0.618(4) -0.1199(11) 0.4673(18) 0.056(9) Uiso 0.032(3) 1 d P B -2
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'
Cl Cl 0.1484 0.1585 '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
O1 C1 N1 125.1(2)
O1 C1 C21 122.2(2)
N1 C1 C21 112.67(19)
C1 N1 C11 128.9(2)
C1 N1 H1 111.7(14)
C11 N1 H1 119.2(14)
C16 C11 C12 117.1(2)
C16 C11 N1 125.5(2)
C12 C11 N1 117.4(2)
C13 C12 F12 119.53(19)
C13 C12 C11 123.6(2)
F12 C12 C11 116.9(2)
C12 C13 C14 118.6(2)
C12 C13 H13 120.7
C14 C13 H13 120.7
C15 C14 C13 119.8(2)
C15 C14 H14 120.1
C13 C14 H14 120.1
C14 C15 C16 120.7(2)
C14 C15 H15 119.6
C16 C15 H15 119.6
C11 C16 C15 120.2(2)
C11 C16 H16 119.9
C15 C16 H16 119.9
N22 C21 C26 123.3(2)
N22 C21 C1 116.5(2)
C26 C21 C1 120.2(2)
C23 N22 C21 117.08(19)
N22 C23 C24 123.4(2)
N22 C23 H23 118.3
C24 C23 H23 118.3
C25 C24 C23 118.6(2)
C25 C24 H24 120.7
C23 C24 H24 120.7
C24 C25 C26 119.3(2)
C24 C25 H25 120.3
C26 C25 H25 120.3
C25 C26 C21 118.3(2)
C25 C26 H26 120.8
C21 C26 H26 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F12 C12 1.370(2)
O1 C1 1.222(2)
C1 N1 1.358(3)
C1 C21 1.505(3)
N1 C11 1.402(3)
N1 H1 0.92(2)
C11 C16 1.388(3)
C11 C12 1.389(3)
C12 C13 1.365(3)
C13 C14 1.383(3)
C13 H13 0.9500
C14 C15 1.382(3)
C14 H14 0.9500
C15 C16 1.390(3)
C15 H15 0.9500
C16 H16 0.9500
C21 N22 1.348(2)
C21 C26 1.384(3)
N22 C23 1.334(3)
C23 C24 1.386(3)
C23 H23 0.9500
C24 C25 1.375(3)
C24 H24 0.9500
C25 C26 1.381(3)
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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 F12 0.92(2) 2.29(2) 2.654(2) 102.8(16) . yes
N1 H1 N22 0.92(2) 2.09(2) 2.630(3) 116.2(17) . yes
C14 H14 O1 0.95 2.55 3.298(3) 136 4_565 yes
C16 H16 O1 0.95 2.37 2.950(3) 119 . 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
O1 C1 N1 C11 4.5(4)
C21 C1 N1 C11 -174.2(2)
C1 N1 C11 C16 -11.2(4)
C1 N1 C11 C12 168.2(2)
C16 C11 C12 C13 0.5(4)
N1 C11 C12 C13 -179.0(2)
C16 C11 C12 F12 179.63(19)
N1 C11 C12 F12 0.1(3)
F12 C12 C13 C14 -179.4(2)
C11 C12 C13 C14 -0.3(4)
C12 C13 C14 C15 0.0(4)
C13 C14 C15 C16 0.2(4)
C12 C11 C16 C15 -0.3(3)
N1 C11 C16 C15 179.1(2)
C14 C15 C16 C11 0.0(4)
O1 C1 C21 N22 -177.9(2)
N1 C1 C21 N22 0.8(3)
O1 C1 C21 C26 1.1(4)
N1 C1 C21 C26 179.9(2)
C26 C21 N22 C23 0.1(3)
C1 C21 N22 C23 179.14(19)
C21 N22 C23 C24 -0.4(4)
N22 C23 C24 C25 -0.1(4)
C23 C24 C25 C26 0.9(4)
C24 C25 C26 C21 -1.2(3)
N22 C21 C26 C25 0.7(4)
C1 C21 C26 C25 -178.3(2)
