#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:22:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180390 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/59/7205991.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_7205991
loop_
_publ_author_name
'Thomas, Lynne H.'
'Craig, Gavin A.'
'Gutmann, Matthias J.'
'Parkin, Andrew'
'Shankland, Kenneth'
'Wilson, Chick C.'
_publ_section_title
;
 Conformational polymorphism of the molecular complex of
 3-fluorobenzoic acid with 4-acetylpyridine
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              3349
_journal_paper_doi               10.1039/c1ce05139c
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C14 H12 F N O3'
_chemical_formula_weight         261.25
_chemical_name_systematic
;
3-fluorobenzoic acid 4-acetylpyridine
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.670(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9892(15)
_cell_length_b                   6.9703(14)
_cell_length_c                   21.947(4)
_cell_measurement_temperature    150(2)
_cell_volume                     1216.2(4)
_computing_cell_refinement       'SXD2001 (Gutmann, 2001)'
_computing_data_collection       'SXD2001 (Gutmann, 2001)'
_computing_data_reduction        'SXD2001 (Gutmann, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device_type  'SXD time-of-flight LAUE diffraction'
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'ISIS spallation source'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.7-6.9
_diffrn_reflns_av_unetI/netI     0.1051
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            7921
_diffrn_reflns_theta_full        83.3
_diffrn_reflns_theta_max         83.3
_diffrn_reflns_theta_min         10.26
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SXD2001 (Gutmann, 2001)'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             322
_exptl_crystal_size_max          6
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          1
_refine_diff_density_max         1.654
_refine_diff_density_min         -1.442
_refine_diff_density_rms         0.339
_refine_ls_extinction_coef       0.00471(18)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         7921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0962
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2423
_reflns_number_gt                7921
_reflns_number_total             7921
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c1ce05139c.txt
_cod_data_source_block           neutron_formII
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7205991
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_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
_atom_site_type_symbol
O1 1.2457(4) -0.5392(5) 0.17327(15) 0.0280(8) Uani d . 1 . . O
N1 0.9394(2) 0.0845(3) 0.14910(9) 0.0206(4) Uani d . 1 . . N
C1 1.0317(3) 0.0015(4) 0.19582(12) 0.0194(5) Uani d . 1 . . C
C2 1.1063(3) -0.1778(4) 0.19098(11) 0.0175(5) Uani d . 1 . . C
C3 1.0863(2) -0.2733(4) 0.13471(11) 0.0148(5) Uani d . 1 . . C
C4 0.9914(3) -0.1849(4) 0.08615(12) 0.0181(5) Uani d . 1 . . C
C5 0.9199(3) -0.0062(4) 0.09536(12) 0.0196(5) Uani d . 1 . . C
C6 1.1684(3) -0.4658(4) 0.12893(11) 0.0171(5) Uani d . 1 . . C
C7 1.1495(3) -0.5634(5) 0.06788(13) 0.0249(6) Uani d . 1 . . C
H1 1.0471(7) 0.0787(10) 0.2390(3) 0.0428(16) Uani d . 1 . . H
H2 1.1794(7) -0.2405(9) 0.2301(3) 0.0369(14) Uani d . 1 . . H
H3 0.9703(8) -0.2520(10) 0.0410(3) 0.0425(15) Uani d . 1 . . H
H4 0.8394(7) 0.0663(10) 0.0588(3) 0.0425(16) Uani d . 1 . . H
H5 1.1982(8) -0.4754(12) 0.0328(3) 0.0493(18) Uani d . 1 . . H
H6 1.0170(7) -0.5885(11) 0.0543(3) 0.0463(17) Uani d . 1 . . H
H7 1.2163(10) -0.6981(11) 0.0698(3) 0.058(2) Uani d . 1 . . H
O2 0.6932(4) 0.3980(6) 0.06542(15) 0.0293(8) Uani d . 1 . . O
O3 0.7801(4) 0.4090(5) 0.16485(15) 0.0250(7) Uani d . 1 . . O
F1 0.3473(4) 1.0067(6) 0.03624(16) 0.0312(8) Uani d . 1 . . F
C8 0.6317(3) 0.7587(4) 0.18115(11) 0.0176(5) Uani d . 1 . . C
C9 0.5551(3) 0.9363(4) 0.18811(13) 0.0208(6) Uani d . 1 . . C
C10 0.4603(3) 1.0215(4) 0.13917(12) 0.0209(6) Uani d . 1 . . C
C11 0.4426(3) 0.9255(4) 0.08338(12) 0.0203(6) Uani d . 1 . . C
C12 0.5160(3) 0.7488(4) 0.07454(12) 0.0177(5) Uani d . 1 . . C
C13 0.6127(3) 0.6651(4) 0.12451(11) 0.0154(5) Uani d . 1 . . C
C14 0.6979(3) 0.4787(4) 0.11517(12) 0.0180(5) Uani d . 1 . . C
H8 0.7076(6) 0.6953(9) 0.2192(2) 0.0324(13) Uani d . 1 . . H
H9 0.5714(7) 1.0056(10) 0.2324(3) 0.0427(15) Uani d . 1 . . H
H10 0.3987(7) 1.1606(10) 0.1438(3) 0.0397(15) Uani d . 1 . . H
H11 0.5010(7) 0.6797(10) 0.0304(3) 0.0378(14) Uani d . 1 . . H
H12 0.8421(6) 0.2784(9) 0.1560(3) 0.0329(13) Uani d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0384(15) 0.023(2) 0.0207(16) 0.0135(13) -0.0092(12) -0.0009(14)
N1 0.0223(7) 0.0161(11) 0.0227(10) 0.0029(7) -0.0003(6) -0.0024(9)
C1 0.0217(9) 0.0188(15) 0.0171(12) 0.0030(10) -0.0017(8) -0.0032(11)
C2 0.0185(9) 0.0196(15) 0.0141(12) 0.0029(9) -0.0003(8) 0.0001(11)
C3 0.0148(8) 0.0157(15) 0.0134(11) -0.0007(8) -0.0008(8) -0.0018(10)
C4 0.0212(9) 0.0187(16) 0.0136(12) 0.0032(9) -0.0028(8) -0.0009(11)
C5 0.0242(10) 0.0157(15) 0.0176(12) 0.0028(9) -0.0039(9) 0.0014(11)
C6 0.0199(9) 0.0162(16) 0.0145(12) 0.0029(9) -0.0022(8) -0.0007(10)
C7 0.0329(13) 0.0244(19) 0.0166(13) 0.0062(11) -0.0017(10) -0.0050(12)
H1 0.053(3) 0.044(4) 0.029(3) 0.008(3) -0.007(2) -0.020(3)
H2 0.045(3) 0.040(4) 0.023(3) 0.011(3) -0.010(2) -0.001(3)
H3 0.058(3) 0.040(5) 0.026(3) 0.008(3) -0.009(2) -0.006(3)
H4 0.054(3) 0.039(4) 0.031(3) 0.011(3) -0.017(2) 0.008(3)
H5 0.060(3) 0.062(6) 0.028(3) -0.001(3) 0.018(3) -0.002(3)
H6 0.045(3) 0.054(5) 0.039(4) -0.001(3) -0.001(3) -0.013(3)
H7 0.086(5) 0.041(5) 0.043(4) 0.037(4) -0.012(3) -0.015(4)
O2 0.0414(15) 0.028(2) 0.0172(15) 0.0107(14) -0.0016(12) -0.0050(14)
O3 0.0339(14) 0.0205(19) 0.0192(15) 0.0109(13) -0.0041(11) 0.0017(14)
F1 0.0306(13) 0.038(2) 0.0241(17) 0.0163(15) -0.0018(12) 0.0057(17)
C8 0.0189(9) 0.0208(16) 0.0130(11) 0.0017(9) 0.0002(8) -0.0005(10)
C9 0.0220(10) 0.0206(16) 0.0196(13) 0.0028(10) 0.0014(9) -0.0020(12)
C10 0.0200(10) 0.0201(17) 0.0222(14) 0.0062(10) 0.0009(9) 0.0015(12)
C11 0.0185(9) 0.0239(16) 0.0182(12) 0.0059(10) 0.0003(8) 0.0036(11)
C12 0.0174(9) 0.0184(16) 0.0174(12) 0.0033(9) 0.0020(9) 0.0014(11)
C13 0.0159(8) 0.0142(14) 0.0159(12) 0.0002(9) 0.0013(8) 0.0031(10)
C14 0.0213(9) 0.0161(16) 0.0165(12) -0.0002(9) 0.0015(8) 0.0018(11)
H8 0.036(2) 0.035(4) 0.024(3) 0.010(2) -0.008(2) 0.004(2)
H9 0.054(3) 0.044(4) 0.028(3) 0.013(3) -0.008(2) -0.018(3)
H10 0.049(3) 0.028(4) 0.041(4) 0.018(3) -0.001(3) 0.000(3)
H11 0.046(3) 0.041(4) 0.025(3) 0.005(3) -0.006(2) -0.006(3)
H12 0.041(3) 0.025(4) 0.032(3) 0.005(2) -0.002(2) -0.003(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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0 0 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 118.8(2) . . ?
N1 C1 C2 122.6(2) . . ?
C1 C2 C3 118.8(2) . . ?
C4 C3 C2 118.2(2) . . ?
C4 C3 C6 122.7(2) . . ?
C2 C3 C6 119.1(2) . . ?
C3 C4 C5 119.0(2) . . ?
N1 C5 C4 122.6(2) . . ?
O1 C6 C7 121.6(3) . . ?
O1 C6 C3 120.0(3) . . ?
C7 C6 C3 118.3(2) . . ?
C9 C8 C13 120.0(2) . . ?
C10 C9 C8 120.5(2) . . ?
C9 C10 C11 118.4(3) . . ?
F1 C11 C12 118.7(3) . . ?
F1 C11 C10 118.3(3) . . ?
C12 C11 C10 122.9(2) . . ?
C11 C12 C13 117.9(2) . . ?
C8 C13 C12 120.2(2) . . ?
C8 C13 C14 121.2(2) . . ?
C12 C13 C14 118.6(2) . . ?
O2 C14 O3 122.7(3) . . ?
O2 C14 C13 123.3(3) . . ?
O3 C14 C13 114.0(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
O1 C6 . 1.213(4) ?
N1 C5 . 1.334(3) ?
N1 C1 . 1.334(3) ?
C1 C2 . 1.393(4) ?
C2 C3 . 1.398(3) ?
C3 C4 . 1.389(3) ?
C3 C6 . 1.504(4) ?
C4 C5 . 1.393(4) ?
C6 C7 . 1.497(4) ?
O2 C14 . 1.226(4) ?
O3 C14 . 1.310(4) ?
F1 C11 . 1.347(4) ?
C8 C9 . 1.396(4) ?
C8 C13 . 1.399(4) ?
C9 C10 . 1.386(4) ?
C10 C11 . 1.390(4) ?
C11 C12 . 1.386(4) ?
C12 C13 . 1.405(3) ?
C13 C14 . 1.490(4) ?
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
O3 H12 N1 1.064(7) 1.574(6) 2.635(4) 174.9(5) .