#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/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/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2423
_reflns_number_gt                7921
_reflns_number_total             7921
_reflns_threshold_expression     >2σ(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_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) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653770
