##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-[Bis(4-fluorophenyl)methyl]piperazin-1-ium 2-hydroxybenzoate
2-hydroxybenzoic acid monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H19 F2 N2 +, C7 H5 O3 -, C7 H6 O3'
_chemical_formula_sum     'C31 H30 F2 N2 O6'
_chemical_formula_iupac     'C17 H19 F2 N2 +, C7 H5 O3 -, C7 H6 O3'
_chemical_formula_weight     564.57
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     33.157(4)
_cell_length_b     10.3007(14)
_cell_length_c     20.105(3)
_cell_angle_alpha     90.00
_cell_angle_beta     124.447(2)
_cell_angle_gamma     90.00
_cell_volume     5662.6(13)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3289
_cell_measurement_theta_min     2.22
_cell_measurement_theta_max     21.41
_cell_measurement_temperature     130(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.39
_exptl_crystal_size_mid     0.37
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.324
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2368
_exptl_absorpt_coefficient_mu     0.101
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.9618
_exptl_absorpt_correction_T_max     0.9802
_exptl_special_details     ?
_diffrn_ambient_temperature     130(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker SMART APEX'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     26180
_diffrn_reflns_av_R_equivalents     0.0453
_diffrn_reflns_av_sigmaI/netI     0.0432
_diffrn_reflns_theta_min     1.49
_diffrn_reflns_theta_max     27.88
_diffrn_reflns_theta_full     27.88
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -43
_diffrn_reflns_limit_h_max     43
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     6761
_reflns_number_gt     4481
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0825
_refine_ls_R_factor_gt     0.0468
_refine_ls_wR_factor_gt     0.1137
_refine_ls_wR_factor_ref     0.1378
_refine_ls_goodness_of_fit_ref     0.856
_refine_ls_restrained_S_all     0.856
_refine_ls_number_reflns     6761
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0737P)²+5.3951P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.270
_refine_diff_density_min     -0.214
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                                  'SHELXTL (Sheldrick, 2008) and local programs'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    F F1 -0.02784(6) 0.43978(13) 0.29760(8) 0.0704(5) Uani d . 1 1 . .
    F F2 0.09200(5) 1.15292(13) 0.19161(7) 0.0558(4) Uani d . 1 1 . .
    N N1 0.13141(5) 0.87077(13) 0.50424(8) 0.0238(3) Uani d . 1 1 . .
    N N2 0.20766(5) 0.90714(14) 0.67270(8) 0.0280(3) Uani d . 1 1 . .
    H H2C 0.1956 0.9716 0.6886 0.034 Uiso calc R 1 1 . .
    H H2D 0.2381 0.8841 0.7166 0.034 Uiso calc R 1 1 . .
    C C1 0.08253(6) 0.89679(16) 0.42988(10) 0.0252(4) Uani d . 1 1 . .
    H H1A 0.0643 0.9543 0.4444 0.030 Uiso calc R 1 1 . .
    C C2 0.12578(6) 0.82397(16) 0.56757(10) 0.0263(4) Uani d . 1 1 . .
    H H2A 0.1049 0.7454 0.5482 0.032 Uiso calc R 1 1 . .
    H H2B 0.1091 0.8913 0.5789 0.032 Uiso calc R 1 1 . .
    C C3 0.17451(6) 0.79218(16) 0.64442(10) 0.0281(4) Uani d . 1 1 . .
    H H3A 0.1695 0.7659 0.6866 0.034 Uiso calc R 1 1 . .
    H H3B 0.1898 0.7185 0.6347 0.034 Uiso calc R 1 1 . .
    C C4 0.21198(6) 0.95705(17) 0.60753(10) 0.0290(4) Uani d . 1 1 . .
    H H4A 0.2281 0.8911 0.5943 0.035 Uiso calc R 1 1 . .
    H H4B 0.2325 1.0363 0.6264 0.035 Uiso calc R 1 1 . .
    C C5 0.16196(6) 0.98805(16) 0.53291(10) 0.0263(4) Uani d . 1 1 . .
    H H5A 0.1462 1.0561 0.5456 0.032 Uiso calc R 1 1 . .
    H H5B 0.1653 1.0215 0.4901 0.032 Uiso calc R 1 1 . .
    C C31 0.08625(6) 0.96641(16) 0.36695(10) 0.0259(4) Uani d . 1 1 . .
    C C32 0.06248(7) 1.08357(19) 0.33563(11) 0.0345(4) Uani d . 1 1 . .
    H H32A 0.0449 1.1213 0.3551 0.041 Uiso calc R 1 1 . .
    C C33 0.06396(7) 1.1470(2) 0.27582(12) 0.0415(5) Uani d . 1 1 . .
    H H33A 0.0473 1.2269 0.2538 0.050 Uiso calc R 1 1 . .
    C C34 0.08997(7) 1.0914(2) 0.24974(11) 0.0370(5) Uani d . 1 1 . .
    C C35 0.11481(7) 0.9764(2) 0.28002(11) 0.0362(4) Uani d . 1 1 . .
    H H35A 0.1332 0.9411 0.2614 0.043 Uiso calc R 1 1 . .
    C C36 0.11238(7) 0.91335(18) 0.33841(11) 0.0319(4) Uani d . 1 1 . .
    H H36A 0.1288 0.8328 0.3593 0.038 Uiso calc R 1 1 . .
    C C41 0.05368(6) 0.77155(17) 0.39516(10) 0.0275(4) Uani d . 1 1 . .
    C C42 0.07650(7) 0.65443(17) 0.40271(11) 0.0338(4) Uani d . 1 1 . .
    H H42A 0.1111 0.6511 0.4311 0.041 Uiso calc R 1 1 . .
    C C43 0.04914(8) 0.54192(19) 0.36909(12) 0.0431(5) Uani d . 1 1 . .
    H H43A 0.0645 0.4613 0.3738 0.052 Uiso calc R 1 1 . .
    C C44 -0.00086(9) 0.5509(2) 0.32877(12) 0.0473(6) Uani d . 1 1 . .
    C C45 -0.02476(8) 0.6645(2) 0.31923(12) 0.0449(5) Uani d . 1 1 . .
    H H45A -0.0594 0.6672 0.2904 0.054 Uiso calc R 1 1 . .
    C C46 0.00301(7) 0.7753(2) 0.35278(11) 0.0350(4) Uani d . 1 1 . .
    H H46A -0.0128 0.8556 0.3468 0.042 Uiso calc R 1 1 . .
    O O11 0.26379(5) 0.42053(13) 0.65952(8) 0.0436(4) Uani d . 1 1 . .
    O O12 0.26128(5) 0.62897(12) 0.62845(8) 0.0369(3) Uani d . 1 1 . .
    H H12 0.2797 0.6354 0.6789 0.055 Uiso calc R 1 1 . .
    O O13 0.21326(9) 0.25463(17) 0.54577(11) 0.0899(7) Uani d . 1 1 . .
    H H13 0.2307 0.2818 0.5935 0.135 Uiso calc R 1 1 . .
    C C10 0.24981(7) 0.50656(17) 0.60834(11) 0.0309(4) Uani d . 1 1 . .
    C C11 0.21896(6) 0.48031(18) 0.52110(11) 0.0319(4) Uani d . 1 1 . .
    C C12 0.20593(7) 0.5776(2) 0.46407(11) 0.0357(4) Uani d . 1 1 . .
    H H12A 0.2171 0.6638 0.4816 0.043 Uiso calc R 1 1 . .
    C C13 0.17710(7) 0.5505(2) 0.38262(12) 0.0450(5) Uani d . 1 1 . .
    H H13A 0.1685 0.6175 0.3443 0.054 Uiso calc R 1 1 . .
    C C14 0.16096(9) 0.4253(3) 0.35743(14) 0.0609(7) Uani d . 1 1 . .
    H H14A 0.1410 0.4064 0.3014 0.073 Uiso calc R 1 1 . .
    C C15 0.17332(11) 0.3276(3) 0.41204(16) 0.0743(9) Uani d . 1 1 . .
    H H15A 0.1621 0.2416 0.3937 0.089 Uiso calc R 1 1 . .
    C C16 0.20226(9) 0.3541(2) 0.49448(14) 0.0554(6) Uani d . 1 1 . .
    O O21 0.30573(5) 0.85892(12) 0.77852(8) 0.0380(3) Uani d . 1 1 . .
    O O22 0.31737(5) 0.64556(11) 0.78271(7) 0.0335(3) Uani d . 1 1 . .
    O O23 0.37289(5) 1.00850(13) 0.88348(10) 0.0485(4) Uani d . 1 1 . .
    H H23 0.3447 0.9876 0.8446 0.073 Uiso calc R 1 1 . .
    C C20 0.33227(6) 0.75940(16) 0.80967(10) 0.0272(4) Uani d . 1 1 . .
    C C21 0.38365(6) 0.77746(16) 0.88016(10) 0.0256(4) Uani d . 1 1 . .
    C C22 0.40114(7) 0.90104(17) 0.91386(11) 0.0314(4) Uani d . 1 1 . .
    C C23 0.44917(7) 0.9159(2) 0.98053(12) 0.0381(5) Uani d . 1 1 . .
    H H23B 0.4610 0.9997 1.0030 0.046 Uiso calc R 1 1 . .
    C C24 0.47949(7) 0.8101(2) 1.01393(12) 0.0400(5) Uani d . 1 1 . .
    H H24A 0.5120 0.8208 1.0601 0.048 Uiso calc R 1 1 . .
    C C25 0.46300(7) 0.6875(2) 0.98067(12) 0.0380(5) Uani d . 1 1 . .
    H H25A 0.4841 0.6146 1.0035 0.046 Uiso calc R 1 1 . .
    C C26 0.41582(7) 0.67260(17) 0.91448(11) 0.0306(4) Uani d . 1 1 . .
    H H26A 0.4048 0.5887 0.8915 0.037 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    F1 C44 . 1.368(2) ?
    F2 C34 . 1.364(2) ?
    N1 C5 . 1.469(2) ?
    N1 C2 . 1.469(2) ?
    N1 C1 . 1.481(2) ?
    N2 C4 . 1.488(2) ?
    N2 C3 . 1.492(2) ?
    N2 H2C . 0.9200 ?
    N2 H2D . 0.9200 ?
    C1 C41 . 1.520(2) ?
    C1 C31 . 1.519(2) ?
    C1 H1A . 1.0000 ?
    C2 C3 . 1.510(2) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.513(2) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C31 C32 . 1.383(2) ?
    C31 C36 . 1.393(2) ?
    C32 C33 . 1.393(3) ?
    C32 H32A . 0.9500 ?
    C33 C34 . 1.363(3) ?
    C33 H33A . 0.9500 ?
    C34 C35 . 1.373(3) ?
    C35 C36 . 1.383(3) ?
    C35 H35A . 0.9500 ?
    C36 H36A . 0.9500 ?
    C41 C42 . 1.386(3) ?
    C41 C46 . 1.389(3) ?
    C42 C43 . 1.389(3) ?
    C42 H42A . 0.9500 ?
    C43 C44 . 1.376(3) ?
    C43 H43A . 0.9500 ?
    C44 C45 . 1.364(3) ?
    C45 C46 . 1.379(3) ?
    C45 H45A . 0.9500 ?
    C46 H46A . 0.9500 ?
    O11 C10 . 1.233(2) ?
    O12 C10 . 1.313(2) ?
    O12 H12 . 0.8400 ?
    O13 C16 . 1.349(3) ?
    O13 H13 . 0.8400 ?
    C10 C11 . 1.472(3) ?
    C11 C16 . 1.396(3) ?
    C11 C12 . 1.395(3) ?
    C12 C13 . 1.379(3) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.379(3) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.370(4) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.394(3) ?
    C15 H15A . 0.9500 ?
    O21 C20 . 1.262(2) ?
    O22 C20 . 1.269(2) ?
    O23 C22 . 1.352(2) ?
    O23 H23 . 0.8400 ?
    C20 C21 . 1.488(2) ?
    C21 C26 . 1.396(2) ?
    C21 C22 . 1.404(2) ?
    C22 C23 . 1.393(3) ?
    C23 C24 . 1.373(3) ?
    C23 H23B . 0.9500 ?
    C24 C25 . 1.388(3) ?
    C24 H24A . 0.9500 ?
    C25 C26 . 1.373(3) ?
    C25 H25A . 0.9500 ?
    C26 H26A . 0.9500 ?
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
    C5 N1 C2 . . 109.10(13) ?
    C5 N1 C1 . . 111.43(12) ?
    C2 N1 C1 . . 109.35(13) ?
    C4 N2 C3 . . 110.84(13) ?
    C4 N2 H2C . . 109.5 ?
    C3 N2 H2C . . 109.5 ?
    C4 N2 H2D . . 109.5 ?
    C3 N2 H2D . . 109.5 ?
    H2C N2 H2D . . 108.1 ?
    N1 C1 C41 . . 110.80(13) ?
    N1 C1 C31 . . 111.61(14) ?
    C41 C1 C31 . . 110.16(13) ?
    N1 C1 H1A . . 108.0 ?
    C41 C1 H1A . . 108.0 ?
    C31 C1 H1A . . 108.0 ?
    N1 C2 C3 . . 111.77(14) ?
    N1 C2 H2A . . 109.3 ?
    C3 C2 H2A . . 109.3 ?
    N1 C2 H2B . . 109.3 ?
    C3 C2 H2B . . 109.3 ?
    H2A C2 H2B . . 107.9 ?
    N2 C3 C2 . . 110.42(13) ?
    N2 C3 H3A . . 109.6 ?
    C2 C3 H3A . . 109.6 ?
    N2 C3 H3B . . 109.6 ?
    C2 C3 H3B . . 109.6 ?
    H3A C3 H3B . . 108.1 ?
    N2 C4 C5 . . 110.40(14) ?
    N2 C4 H4A . . 109.6 ?
    C5 C4 H4A . . 109.6 ?
    N2 C4 H4B . . 109.6 ?
    C5 C4 H4B . . 109.6 ?
    H4A C4 H4B . . 108.1 ?
    N1 C5 C4 . . 109.97(13) ?
    N1 C5 H5A . . 109.7 ?
    C4 C5 H5A . . 109.7 ?
    N1 C5 H5B . . 109.7 ?
    C4 C5 H5B . . 109.7 ?
    H5A C5 H5B . . 108.2 ?
    C32 C31 C36 . . 118.80(16) ?
    C32 C31 C1 . . 119.83(16) ?
    C36 C31 C1 . . 121.36(15) ?
    C31 C32 C33 . . 120.86(18) ?
    C31 C32 H32A . . 119.6 ?
    C33 C32 H32A . . 119.6 ?
    C34 C33 C32 . . 118.29(18) ?
    C34 C33 H33A . . 120.9 ?
    C32 C33 H33A . . 120.9 ?
    F2 C34 C35 . . 118.22(19) ?
    F2 C34 C33 . . 118.89(18) ?
    C35 C34 C33 . . 122.89(18) ?
    C34 C35 C36 . . 118.25(18) ?
    C34 C35 H35A . . 120.9 ?
    C36 C35 H35A . . 120.9 ?
    C35 C36 C31 . . 120.89(17) ?
    C35 C36 H36A . . 119.6 ?
    C31 C36 H36A . . 119.6 ?
    C42 C41 C46 . . 119.15(17) ?
    C42 C41 C1 . . 121.71(16) ?
    C46 C41 C1 . . 119.11(16) ?
    C41 C42 C43 . . 120.49(19) ?
    C41 C42 H42A . . 119.8 ?
    C43 C42 H42A . . 119.8 ?
    C44 C43 C42 . . 117.9(2) ?
    C44 C43 H43A . . 121.1 ?
    C42 C43 H43A . . 121.1 ?
    C45 C44 F1 . . 118.4(2) ?
    C45 C44 C43 . . 123.46(18) ?
    F1 C44 C43 . . 118.1(2) ?
    C44 C45 C46 . . 117.8(2) ?
    C44 C45 H45A . . 121.1 ?
    C46 C45 H45A . . 121.1 ?
    C45 C46 C41 . . 121.2(2) ?
    C45 C46 H46A . . 119.4 ?
    C41 C46 H46A . . 119.4 ?
    C10 O12 H12 . . 109.5 ?
    C16 O13 H13 . . 109.5 ?
    O11 C10 O12 . . 121.78(16) ?
    O11 C10 C11 . . 122.85(17) ?
    O12 C10 C11 . . 115.37(16) ?
    C16 C11 C12 . . 118.86(18) ?
    C16 C11 C10 . . 119.05(18) ?
    C12 C11 C10 . . 122.08(17) ?
    C13 C12 C11 . . 121.03(19) ?
    C13 C12 H12A . . 119.5 ?
    C11 C12 H12A . . 119.5 ?
    C14 C13 C12 . . 119.3(2) ?
    C14 C13 H13A . . 120.3 ?
    C12 C13 H13A . . 120.3 ?
    C13 C14 C15 . . 121.0(2) ?
    C13 C14 H14A . . 119.5 ?
    C15 C14 H14A . . 119.5 ?
    C14 C15 C16 . . 120.1(2) ?
    C14 C15 H15A . . 119.9 ?
    C16 C15 H15A . . 119.9 ?
    O13 C16 C15 . . 117.8(2) ?
    O13 C16 C11 . . 122.5(2) ?
    C15 C16 C11 . . 119.7(2) ?
    C22 O23 H23 . . 109.5 ?
    O21 C20 O22 . . 123.02(16) ?
    O21 C20 C21 . . 118.18(15) ?
    O22 C20 C21 . . 118.80(15) ?
    C26 C21 C22 . . 118.14(16) ?
    C26 C21 C20 . . 121.14(15) ?
    C22 C21 C20 . . 120.72(15) ?
    O23 C22 C23 . . 117.87(16) ?
    O23 C22 C21 . . 122.19(16) ?
    C23 C22 C21 . . 119.94(17) ?
    C24 C23 C22 . . 120.37(18) ?
    C24 C23 H23B . . 119.8 ?
    C22 C23 H23B . . 119.8 ?
    C23 C24 C25 . . 120.42(18) ?
    C23 C24 H24A . . 119.8 ?
    C25 C24 H24A . . 119.8 ?
    C26 C25 C24 . . 119.40(18) ?
    C26 C25 H25A . . 120.3 ?
    C24 C25 H25A . . 120.3 ?
    C25 C26 C21 . . 121.71(17) ?
    C25 C26 H26A . . 119.1 ?
    C21 C26 H26A . . 119.1 ?
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
    C5 N1 C1 C41 . . . . 172.94(14) ?
    C2 N1 C1 C41 . . . . -66.37(17) ?
    C5 N1 C1 C31 . . . . 49.78(18) ?
    C2 N1 C1 C31 . . . . 170.47(13) ?
    C5 N1 C2 C3 . . . . -59.47(17) ?
    C1 N1 C2 C3 . . . . 178.43(13) ?
    C4 N2 C3 C2 . . . . -53.61(19) ?
    N1 C2 C3 N2 . . . . 55.98(18) ?
    C3 N2 C4 C5 . . . . 55.80(18) ?
    C2 N1 C5 C4 . . . . 60.67(18) ?
    C1 N1 C5 C4 . . . . -178.49(14) ?
    N2 C4 C5 N1 . . . . -59.57(18) ?
    N1 C1 C31 C32 . . . . -123.99(17) ?
    C41 C1 C31 C32 . . . . 112.49(18) ?
    N1 C1 C31 C36 . . . . 57.4(2) ?
    C41 C1 C31 C36 . . . . -66.1(2) ?
    C36 C31 C32 C33 . . . . 0.9(3) ?
    C1 C31 C32 C33 . . . . -177.75(17) ?
    C31 C32 C33 C34 . . . . -0.8(3) ?
    C32 C33 C34 F2 . . . . -179.56(17) ?
    C32 C33 C34 C35 . . . . -0.3(3) ?
    F2 C34 C35 C36 . . . . -179.38(16) ?
    C33 C34 C35 C36 . . . . 1.3(3) ?
    C34 C35 C36 C31 . . . . -1.3(3) ?
    C32 C31 C36 C35 . . . . 0.2(3) ?
    C1 C31 C36 C35 . . . . 178.82(16) ?
    N1 C1 C41 C42 . . . . -32.2(2) ?
    C31 C1 C41 C42 . . . . 91.76(19) ?
    N1 C1 C41 C46 . . . . 149.63(16) ?
    C31 C1 C41 C46 . . . . -86.38(19) ?
    C46 C41 C42 C43 . . . . -0.7(3) ?
    C1 C41 C42 C43 . . . . -178.80(16) ?
    C41 C42 C43 C44 . . . . -0.3(3) ?
    C42 C43 C44 C45 . . . . 1.0(3) ?
    C42 C43 C44 F1 . . . . -178.13(17) ?
    F1 C44 C45 C46 . . . . 178.36(17) ?
    C43 C44 C45 C46 . . . . -0.8(3) ?
    C44 C45 C46 C41 . . . . -0.2(3) ?
    C42 C41 C46 C45 . . . . 0.9(3) ?
    C1 C41 C46 C45 . . . . 179.10(17) ?
    O11 C10 C11 C16 . . . . 3.9(3) ?
    O12 C10 C11 C16 . . . . -175.59(19) ?
    O11 C10 C11 C12 . . . . -176.00(18) ?
    O12 C10 C11 C12 . . . . 4.6(3) ?
    C16 C11 C12 C13 . . . . -0.1(3) ?
    C10 C11 C12 C13 . . . . 179.79(18) ?
    C11 C12 C13 C14 . . . . 0.0(3) ?
    C12 C13 C14 C15 . . . . -0.3(4) ?
    C13 C14 C15 C16 . . . . 0.6(5) ?
    C14 C15 C16 O13 . . . . 179.8(3) ?
    C14 C15 C16 C11 . . . . -0.6(5) ?
    C12 C11 C16 O13 . . . . 180.0(2) ?
    C10 C11 C16 O13 . . . . 0.1(4) ?
    C12 C11 C16 C15 . . . . 0.3(4) ?
    C10 C11 C16 C15 . . . . -179.5(2) ?
    O21 C20 C21 C26 . . . . -176.14(16) ?
    O22 C20 C21 C26 . . . . 2.6(3) ?
    O21 C20 C21 C22 . . . . 3.7(3) ?
    O22 C20 C21 C22 . . . . -177.59(16) ?
    C26 C21 C22 O23 . . . . 178.55(17) ?
    C20 C21 C22 O23 . . . . -1.3(3) ?
    C26 C21 C22 C23 . . . . -1.0(3) ?
    C20 C21 C22 C23 . . . . 179.13(17) ?
    O23 C22 C23 C24 . . . . 179.95(18) ?
    C21 C22 C23 C24 . . . . -0.5(3) ?
    C22 C23 C24 C25 . . . . 1.4(3) ?
    C23 C24 C25 C26 . . . . -0.7(3) ?
    C24 C25 C26 C21 . . . . -0.8(3) ?
    C22 C21 C26 C25 . . . . 1.7(3) ?
    C20 C21 C26 C25 . . . . -178.48(17) ?
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
    N2 H2C O22 4_556 0.9200 2.0000 2.892(2) 162.00 yes
    N2 H2D O21 . 0.9200 1.8700 2.742(2) 158.00 yes
    O12 H12 O22 . 0.8400 1.7300 2.5654(18) 179.00 yes
    O13 H13 O11 . 0.8400 1.8300 2.574(2) 146.00 yes
    O23 H23 O21 . 0.8400 1.8000 2.544(2) 146.00 yes
data_global
_journal_date_recd_electronic     2012-03-20
_journal_date_accepted     2012-03-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o1180
_journal_page_last     o1180
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812012329
_journal_coeditor_code     BT5853
_publ_contact_author_name
;
Dr Ulrich Flörke
;
_publ_contact_author_address
;
Anorganische und Analytische Chemie
Universität Paderborn
Warburgerstrasse 100
D-33098 Paderborn
Germany
;
_publ_contact_author_email     ulrich.floerke@upb.de
_publ_contact_author_fax     '+49 5251 60 3423'
_publ_contact_author_phone     '+49 5251 60 2496'
_publ_section_title
;
4-[Bis(4-fluorophenyl)methyl]piperazin-1-ium 2-hydroxybenzoate 2-hydroxybenzoic
acid monosolvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Dayananda, A. S.' ?
;
Department of Studies in Chemistry,
University of Mysore, Manasagangotri,
Mysore 570 006, India
;
    'Yathirajan, H. S.' ?
;
Department of Studies in Chemistry,
University of Mysore, Manasagangotri,
Mysore 570 006, India
;
    'Flörke, Ulrich' ?
;
Department Chemie
Fakultät für Naturwissenschaften
Universität Paderborn
Warburgerstrasse 100
D-33098 Paderborn, Germany
;
