#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:23:26 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179628 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/92/4509272.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509272
loop_
_publ_author_name
'Sarma, Bipul'
'Nath, Naba K.'
'Bhogala, Balakrishna R.'
'Nangia, Ashwini'
_publ_section_title
;
 Synthon Competition and Cooperation in Molecular Salts of Hydroxybenzoic
 Acids and Aminopyridines
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1546
_journal_paper_doi               10.1021/cg801145c
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         C7H4FO3.C5H7N2.H2O
_chemical_formula_sum            'C12 H13 F N2 O4'
_chemical_formula_weight         268.24
_chemical_name_systematic
; 
 4-Aminopyridinium 3-flouro-4-hydroxybenzoate hydrate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.314(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1711(7)
_cell_length_b                   12.8232(13)
_cell_length_c                   13.2749(14)
_cell_measurement_reflns_used    3720
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.85
_cell_volume                     1215.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7888
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0691P)²+0.2950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                2011
_reflns_number_total             2380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg801145csup2.cif
_cod_data_source_block           an441_m_4-APH+.3-F-4-HBA-.H2O_1:1:1_(5)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4509272
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1 F -0.0878(2) 0.47781(9) 0.17737(10) 0.0605(5) Uani 1 1 d .
O1 O 0.3304(2) 0.71324(12) 0.51120(12) 0.0528(5) Uani 1 1 d .
O2 O 0.2591(2) 0.54574(12) 0.51439(12) 0.0550(5) Uani 1 1 d .
O3 O -0.1264(2) 0.65703(12) 0.07998(11) 0.0465(4) Uani 1 1 d .
C2 C 0.1392(3) 0.64339(15) 0.37208(14) 0.0328(5) Uani 1 1 d .
C3 C 0.0660(3) 0.55525(15) 0.32265(14) 0.0351(5) Uani 1 1 d .
H3 H 0.0753 0.4906 0.3545 0.042 Uiso 1 1 calc R
C10 C 0.6287(3) 0.47503(16) 0.88239(15) 0.0365(5) Uani 1 1 d .
C5 C -0.0410(3) 0.65806(15) 0.17536(15) 0.0351(5) Uani 1 1 d .
N1 N 0.4492(3) 0.52293(16) 0.69552(14) 0.0480(5) Uani 1 1 d .
C9 C 0.5418(3) 0.39853(17) 0.81939(15) 0.0408(5) Uani 1 1 d .
H9 H 0.5432 0.3294 0.8405 0.049 Uiso 1 1 calc R
C4 C -0.0200(3) 0.56412(15) 0.22659(15) 0.0358(5) Uani 1 1 d .
C1 C 0.2494(3) 0.63429(16) 0.47354(15) 0.0377(5) Uani 1 1 d .
C6 C 0.0305(3) 0.74557(16) 0.22563(17) 0.0476(6) Uani 1 1 d .
H6 H 0.0184 0.8104 0.1943 0.057 Uiso 1 1 calc R
C7 C 0.1198(3) 0.73785(16) 0.32203(16) 0.0446(6) Uani 1 1 d .
H7 H 0.1682 0.7978 0.3541 0.054 Uiso 1 1 calc R
C11 C 0.6185(4) 0.57844(17) 0.84613(17) 0.0499(6) Uani 1 1 d .
H11 H 0.6723 0.6326 0.8854 0.060 Uiso 1 1 calc R
N2 N 0.7167(3) 0.45028(19) 0.97149(14) 0.0494(5) Uani 1 1 d .
C8 C 0.4553(3) 0.42455(18) 0.72766(16) 0.0451(6) Uani 1 1 d .
H8 H 0.3992 0.3726 0.6864 0.054 Uiso 1 1 calc R
C12 C 0.5297(4) 0.59819(18) 0.75375(18) 0.0555(7) Uani 1 1 d .
H12 H 0.5247 0.6665 0.7300 0.067 Uiso 1 1 calc R
O4 O 0.7143(3) 0.83167(15) 0.01682(16) 0.0657(6) Uani 1 1 d .
H4B H 0.603(5) 0.824(2) 0.021(2) 0.074(11) Uiso 1 1 d .
H2A H 0.771(3) 0.503(2) 1.008(2) 0.049(7) Uiso 1 1 d .
H4A H 0.739(5) 0.909(3) 0.013(3) 0.108(12) Uiso 1 1 d .
H2B H 0.723(4) 0.380(2) 0.988(2) 0.061(8) Uiso 1 1 d .
H3A H -0.158(4) 0.725(3) 0.062(2) 0.083(10) Uiso 1 1 d .
H1 H 0.393(4) 0.539(2) 0.633(2) 0.063(8) Uiso 1 1 d .
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
C5 O3 H3A 108.0(19)
C7 C2 C3 118.06(17)
C7 C2 C1 121.36(17)
C3 C2 C1 120.41(17)
C4 C3 C2 119.45(18)
C4 C3 H3 120.3
C2 C3 H3 120.3
N2 C10 C9 121.0(2)
N2 C10 C11 122.3(2)
C9 C10 C11 116.71(18)
O3 C5 C6 125.14(18)
O3 C5 C4 118.03(17)
C6 C5 C4 116.82(18)
C8 N1 C12 120.0(2)
C8 N1 H1 120.4(17)
C12 N1 H1 119.6(17)
C8 C9 C10 120.4(2)
C8 C9 H9 119.8
C10 C9 H9 119.8
F1 C4 C3 119.53(17)
F1 C4 C5 117.18(17)
C3 C4 C5 123.30(18)
O1 C1 O2 123.66(18)
O1 C1 C2 118.87(18)
O2 C1 C2 117.43(17)
C5 C6 C7 120.64(19)
C5 C6 H6 119.7
C7 C6 H6 119.7
C6 C7 C2 121.72(19)
C6 C7 H7 119.1
C2 C7 H7 119.1
C12 C11 C10 119.4(2)
C12 C11 H11 120.3
C10 C11 H11 120.3
C10 N2 H2A 116.8(16)
C10 N2 H2B 116.7(17)
H2A N2 H2B 126(2)
N1 C8 C9 121.3(2)
N1 C8 H8 119.3
C9 C8 H8 119.3
N1 C12 C11 122.2(2)
N1 C12 H12 118.9
C11 C12 H12 118.9
H4B O4 H4A 108(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C4 1.352(2)
O1 C1 1.249(2)
O2 C1 1.257(2)
O3 C5 1.354(2)
O3 H3A 0.92(3)
C2 C7 1.382(3)
C2 C3 1.385(3)
C2 C1 1.501(3)
C3 C4 1.369(3)
C3 H3 0.9300
C10 N2 1.326(3)
C10 C9 1.398(3)
C10 C11 1.410(3)
C5 C6 1.380(3)
C5 C4 1.385(3)
N1 C8 1.331(3)
N1 C12 1.334(3)
N1 H1 0.91(3)
C9 C8 1.356(3)
C9 H9 0.9300
C6 C7 1.381(3)
C6 H6 0.9300
C7 H7 0.9300
C11 C12 1.352(3)
C11 H11 0.9300
N2 H2A 0.90(3)
N2 H2B 0.92(3)
C8 H8 0.9300
C12 H12 0.9300
O4 H4B 0.81(3)
O4 H4A 1.01(4)
