##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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# This file may be used for bona fide research purposes within the           #
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data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Imidazolium hydrogen 2,3,5,6-tetrafluoroterephthalate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C3 H5 N2 + , C8 F4 H1 O4 -'
_chemical_formula_sum     'C11 H6 F4 N2 O4'
_chemical_formula_iupac     'C3 H5 N2 + , C8 F4 H1 O4 -'
_chemical_formula_weight     306.18
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
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'
_cell_length_a     9.716(3)
_cell_length_b     7.229(3)
_cell_length_c     17.406(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1222.5(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3571
_cell_measurement_theta_min     2.34
_cell_measurement_theta_max     27.56
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.664
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     616
_exptl_absorpt_coefficient_mu     0.165
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.9521
_exptl_absorpt_correction_T_max     0.9677
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     0
_diffrn_reflns_number     9957
_diffrn_reflns_av_R_equivalents     0.0287
_diffrn_reflns_av_sigmaI/netI     0.0178
_diffrn_reflns_theta_min     2.34
_diffrn_reflns_theta_max     27.56
_diffrn_reflns_theta_full     27.56
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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     1457
_reflns_number_gt     1330
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0296
_refine_ls_R_factor_gt     0.0265
_refine_ls_wR_factor_gt     0.0711
_refine_ls_wR_factor_ref     0.0735
_refine_ls_goodness_of_fit_ref     1.078
_refine_ls_restrained_S_all     1.076
_refine_ls_number_reflns     1457
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0451P)²+0.0992P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_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     0.248
_refine_diff_density_min     -0.155
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.018(2)
_refine_ls_extinction_expression
                                'Fc^*^ = kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_disorder_assembly
    _atom_site_disorder_group
    F F1 0.42776(14) 0.5920(2) -0.07757(7) 0.0454(3) Uani d . 1 . .
    F F2 0.69164(13) 0.6496(2) -0.04859(8) 0.0462(3) Uani d . 1 . .
    F F3 0.36969(12) 0.3520(2) 0.17285(7) 0.0455(3) Uani d . 1 . .
    F F4 0.63344(13) 0.4084(2) 0.20130(8) 0.0468(3) Uani d . 1 . .
    O O1 0.20150(16) 0.3642(2) -0.02812(8) 0.0410(4) Uani d . 1 . .
    O O2 0.15456(14) 0.5081(2) 0.08150(8) 0.0377(4) Uani d . 1 . .
    O O3 0.90284(14) 0.4847(2) 0.04279(10) 0.0407(4) Uani d D 1 . .
    H H3 0.9832 0.4958 0.0564 0.061 Uiso d RD 1 . .
    O O4 0.85978(15) 0.6410(3) 0.15075(9) 0.0458(4) Uani d . 1 . .
    C C1 0.38844(19) 0.4724(3) 0.04701(12) 0.0273(4) Uani d . 1 . .
    C C2 0.4755(2) 0.5446(3) -0.00816(11) 0.0297(4) Uani d . 1 . .
    C C3 0.6137(2) 0.5735(3) 0.00650(12) 0.0308(4) Uani d . 1 . .
    C C4 0.6716(2) 0.5305(3) 0.07715(12) 0.0293(4) Uani d . 1 . .
    C C5 0.5845(2) 0.4576(3) 0.13208(12) 0.0301(4) Uani d . 1 . .
    C C6 0.4463(2) 0.4288(3) 0.11741(12) 0.0296(4) Uani d . 1 . .
    C C7 0.23534(19) 0.4443(3) 0.03141(11) 0.0278(4) Uani d . 1 . .
    C C8 0.8223(2) 0.5593(3) 0.09441(12) 0.0303(4) Uani d . 1 . .
    N N1 0.1433(2) 0.5881(3) 0.24288(12) 0.0513(5) Uani d D 1 . .
    H H1 0.1559 0.5844 0.1940 0.077 Uiso d RD 1 . .
    N N2 0.1630(2) 0.6764(3) 0.35864(12) 0.0453(5) Uani d D 1 . .
    H H2 0.1944 0.7350 0.3979 0.068 Uiso d RD 1 . .
    C C9 0.2114(3) 0.6965(4) 0.28898(14) 0.0514(6) Uani d . 1 . .
    H H9A 0.2828 0.7751 0.2748 0.062 Uiso calc R 1 . .
    C C10 0.0465(3) 0.4950(4) 0.28392(15) 0.0527(6) Uani d . 1 . .
    H H10A -0.0160 0.4090 0.2649 0.063 Uiso calc R 1 . .
    C C11 0.0584(3) 0.5505(4) 0.35669(15) 0.0540(7) Uani d . 1 . .
    H H11A 0.0056 0.5110 0.3981 0.065 Uiso calc R 1 . .
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
    F1 0.0323(7) 0.0729(9) 0.0310(6) -0.0017(6) -0.0050(5) 0.0119(6)
    F2 0.0278(6) 0.0714(9) 0.0395(7) -0.0075(6) 0.0069(5) 0.0144(7)
    F3 0.0275(6) 0.0703(9) 0.0386(7) -0.0063(6) 0.0045(5) 0.0152(7)
    F4 0.0293(7) 0.0746(9) 0.0365(7) -0.0025(6) -0.0063(5) 0.0153(7)
    O1 0.0272(7) 0.0602(10) 0.0357(8) 0.0000(7) -0.0019(6) -0.0145(7)
    O2 0.0185(6) 0.0610(9) 0.0336(7) 0.0001(6) 0.0015(6) -0.0128(7)
    O3 0.0171(6) 0.0628(9) 0.0422(8) -0.0002(6) -0.0007(6) -0.0144(8)
    O4 0.0295(8) 0.0667(11) 0.0412(9) -0.0031(7) -0.0027(7) -0.0147(8)
    C1 0.0189(8) 0.0325(9) 0.0304(9) 0.0017(7) 0.0013(8) -0.0036(7)
    C2 0.0240(10) 0.0388(10) 0.0262(9) 0.0028(8) -0.0023(8) 0.0004(7)
    C3 0.0224(9) 0.0372(10) 0.0328(10) -0.0005(8) 0.0046(8) 0.0029(8)
    C4 0.0194(8) 0.0345(9) 0.0341(10) 0.0006(7) 0.0001(8) -0.0024(8)
    C5 0.0221(9) 0.0390(10) 0.0293(9) 0.0020(8) -0.0005(8) 0.0015(8)
    C6 0.0209(9) 0.0378(10) 0.0301(9) -0.0005(8) 0.0045(7) 0.0026(8)
    C7 0.0176(8) 0.0363(9) 0.0296(10) 0.0004(7) -0.0001(8) -0.0009(7)
    C8 0.0203(9) 0.0376(9) 0.0330(10) -0.0018(7) -0.0006(8) 0.0003(8)
    N1 0.0480(12) 0.0780(14) 0.0279(9) 0.0091(10) -0.0018(9) -0.0079(10)
    N2 0.0495(11) 0.0558(11) 0.0304(8) 0.0031(9) -0.0080(8) -0.0100(8)
    C9 0.0479(14) 0.0661(15) 0.0403(12) -0.0060(12) -0.0003(12) 0.0038(12)
    C10 0.0513(15) 0.0611(14) 0.0458(13) -0.0049(13) -0.0130(13) -0.0068(12)
    C11 0.0472(15) 0.0775(18) 0.0371(12) -0.0058(12) 0.0018(11) 0.0066(12)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 C2 . 1.339(2) ?
    F2 C3 . 1.340(2) ?
    F3 C6 . 1.339(2) ?
    F4 C5 . 1.343(2) ?
    O1 C7 . 1.232(2) ?
    O2 C7 . 1.261(2) ?
    O3 C8 . 1.308(3) ?
    O3 H3 . 0.8199 ?
    O4 C8 . 1.201(3) ?
    C1 C2 . 1.382(3) ?
    C1 C6 . 1.385(3) ?
    C1 C7 . 1.526(3) ?
    C2 C3 . 1.382(3) ?
    C3 C4 . 1.388(3) ?
    C4 C5 . 1.382(3) ?
    C4 C8 . 1.509(3) ?
    C5 C6 . 1.382(3) ?
    N1 C9 . 1.302(3) ?
    N1 C10 . 1.359(4) ?
    N1 H1 . 0.8600 ?
    N2 C9 . 1.309(3) ?
    N2 C11 . 1.364(4) ?
    N2 H2 . 0.8600 ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.334(4) ?
    C10 H10A . 0.9300 ?
    C11 H11A . 0.9300 ?
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
    C8 O3 H3 . . 109.4 ?
    C2 C1 C6 . . 116.88(16) ?
    C2 C1 C7 . . 121.55(18) ?
    C6 C1 C7 . . 121.57(18) ?
    F1 C2 C1 . . 120.78(17) ?
    F1 C2 C3 . . 117.67(17) ?
    C1 C2 C3 . . 121.55(18) ?
    F2 C3 C2 . . 118.62(18) ?
    F2 C3 C4 . . 119.76(18) ?
    C2 C3 C4 . . 121.59(18) ?
    C5 C4 C3 . . 116.73(17) ?
    C5 C4 C8 . . 120.63(19) ?
    C3 C4 C8 . . 122.64(18) ?
    F4 C5 C4 . . 120.31(17) ?
    F4 C5 C6 . . 118.02(18) ?
    C4 C5 C6 . . 121.65(19) ?
    F3 C6 C5 . . 117.99(19) ?
    F3 C6 C1 . . 120.39(18) ?
    C5 C6 C1 . . 121.60(19) ?
    O1 C7 O2 . . 126.00(18) ?
    O1 C7 C1 . . 118.19(17) ?
    O2 C7 C1 . . 115.81(18) ?
    O4 C8 O3 . . 125.59(19) ?
    O4 C8 C4 . . 121.64(19) ?
    O3 C8 C4 . . 112.77(18) ?
    C9 N1 C10 . . 109.0(2) ?
    C9 N1 H1 . . 123.8 ?
    C10 N1 H1 . . 127.1 ?
    C9 N2 C11 . . 108.6(2) ?
    C9 N2 H2 . . 123.6 ?
    C11 N2 H2 . . 127.8 ?
    N1 C9 N2 . . 108.7(3) ?
    N1 C9 H9A . . 125.6 ?
    N2 C9 H9A . . 125.6 ?
    C11 C10 N1 . . 106.9(2) ?
    C11 C10 H10A . . 126.6 ?
    N1 C10 H10A . . 126.6 ?
    C10 C11 N2 . . 106.8(2) ?
    C10 C11 H11A . . 126.6 ?
    N2 C11 H11A . . 126.6 ?
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
    C6 C1 C2 F1 . . . . -179.39(17) ?
    C7 C1 C2 F1 . . . . -0.2(3) ?
    C6 C1 C2 C3 . . . . -0.6(3) ?
    C7 C1 C2 C3 . . . . 178.64(18) ?
    F1 C2 C3 F2 . . . . 1.0(3) ?
    C1 C2 C3 F2 . . . . -177.83(17) ?
    F1 C2 C3 C4 . . . . 179.23(18) ?
    C1 C2 C3 C4 . . . . 0.4(3) ?
    F2 C3 C4 C5 . . . . 178.10(19) ?
    C2 C3 C4 C5 . . . . -0.1(3) ?
    F2 C3 C4 C8 . . . . -2.3(3) ?
    C2 C3 C4 C8 . . . . 179.48(19) ?
    C3 C4 C5 F4 . . . . 178.45(18) ?
    C8 C4 C5 F4 . . . . -1.1(3) ?
    C3 C4 C5 C6 . . . . 0.0(3) ?
    C8 C4 C5 C6 . . . . -179.55(19) ?
    F4 C5 C6 F3 . . . . -0.6(3) ?
    C4 C5 C6 F3 . . . . 177.86(18) ?
    F4 C5 C6 C1 . . . . -178.71(17) ?
    C4 C5 C6 C1 . . . . -0.3(3) ?
    C2 C1 C6 F3 . . . . -177.56(18) ?
    C7 C1 C6 F3 . . . . 3.2(3) ?
    C2 C1 C6 C5 . . . . 0.5(3) ?
    C7 C1 C6 C5 . . . . -178.70(19) ?
    C2 C1 C7 O1 . . . . 49.2(3) ?
    C6 C1 C7 O1 . . . . -131.6(2) ?
    C2 C1 C7 O2 . . . . -130.3(2) ?
    C6 C1 C7 O2 . . . . 48.9(3) ?
    C5 C4 C8 O4 . . . . -51.2(3) ?
    C3 C4 C8 O4 . . . . 129.2(2) ?
    C5 C4 C8 O3 . . . . 127.9(2) ?
    C3 C4 C8 O3 . . . . -51.6(3) ?
    C10 N1 C9 N2 . . . . 0.3(3) ?
    C11 N2 C9 N1 . . . . -0.5(3) ?
    C9 N1 C10 C11 . . . . -0.1(3) ?
    N1 C10 C11 N2 . . . . -0.2(3) ?
    C9 N2 C11 C10 . . . . 0.4(3) ?
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
    N1 H1 O2 . 0.86 2.03 2.870(3) 163.7
    N2 H2 O1 4 0.86 1.89 2.732(3) 167.8
    O3 H3 O2 1_655 0.82 1.72 2.5425(19) 176.6
    C9 H9A O4 3_465 0.93 2.36 3.041(3) 129.5
    C11 H11A O1 2_565 0.93 2.55 3.283(3) 135.8
data_global
_journal_date_recd_electronic     2009-12-30
_journal_date_accepted     2010-02-02
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o179
_journal_page_last     o181
_journal_paper_category     FO
_journal_coeditor_code     SQ3234
_publ_contact_author_name     'Qi Liu'
_publ_contact_author_address
;
School of Chemistry and Chemical Engineering
Jiangsu Polytechnic University
Changzhou 213164
Jiangsu
People's Republic of China
;
_publ_contact_author_email     liuqi62@163.com
_publ_contact_author_phone         .519E-305
_publ_section_title
;
Three-dimensional supramolecular architecture in imidazolium hydrogen
2,3,5,6-tetrafluoroterephthalate
;
loop_
    _publ_author_name
    _publ_author_address
    'Yu, Li-Li'
;
Key Laboratory of Fine Petrochemical Technology
School of Chemistry and Chemical Engineering
Jiangsu Polytechnic University
Changzhou 213164
Jiangsu
People's Republic of China
;
    'Cheng, Mei-Ling'
;
Key Laboratory of Fine Petrochemical Technology
School of Chemistry and Chemical Engineering
Jiangsu Polytechnic University
Changzhou 213164
Jiangsu
People's Republic of China
;
    'Liu, Qi'
;
Key Laboratory of Fine Petrochemical Technology
School of Chemistry and Chemical Engineering
Jiangsu Polytechnic University
Changzhou 213164
Jiangsu
People's Republic of China
;
    'Zhang, Zhi-Hui'
;
Key Laboratory of Fine Petrochemical Technology
School of Chemistry and Chemical Engineering
Jiangsu Polytechnic University
Changzhou 213164
Jiangsu
People's Republic of China
;
    'Chen, Qun'
;
Key Laboratory of Fine Petrochemical Technology
School of Chemistry and Chemical Engineering
Jiangsu Polytechnic University
Changzhou 213164
Jiangsu
People's Republic of China
;
