##############################################################################
###                                                                        ###
###           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/  #
# cif/home.html                                                              #
#                                                                            #
# 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     SHELXL97
_chemical_name_systematic
;
1-(diaminomethylene)thiouron-1-ium hydrogen difluoride
;
_chemical_formula_moiety     'C2 H7 N4 S + , F2 H -'
_chemical_formula_sum     'C2 H8 F2 N4 S'
_chemical_formula_iupac     'C2 H7 N4 S + , H F2 -'
_chemical_formula_weight     158.18
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.199(3)
_cell_length_b     12.203(4)
_cell_length_c     14.158(4)
_cell_angle_alpha     100.78(3)
_cell_angle_beta     93.87(3)
_cell_angle_gamma     104.50(3)
_cell_volume     1337.5(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8334
_cell_measurement_theta_min     2.95
_cell_measurement_theta_max     36.79
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.19
_exptl_crystal_size_mid     0.09
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.571
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.443
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details     '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_absorpt_correction_T_min     0.897
_exptl_absorpt_correction_T_max     0.979
_exptl_special_details
;
IR spectra were collected on BRUKER spectrometer for samples suspended in nujol
mull (KBr windows). (I): 435.6 (w), 516.0 (vw), 560.2 (vw), 632.2 (w), 734.4
(m), 829.5 (vw), 910.6 (vw), 993.2 (vw), 1105.1 (w), 1180.5 (m),
1248.0 (s), 1338.7 (s), 1462.3 (m), 1511.5 (s),
1530.3 (s), 1607.5 (vs), 1647.3 (s), 1710.1
(vs), 2854.1 (s), 2924.6 (vs), 3118.0
(vs), 3351.6 (vs)
;
_diffrn_ambient_temperature     100(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     'Oxford Diffraction KM4 CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20685
_diffrn_reflns_av_R_equivalents     0.0511
_diffrn_reflns_av_sigmaI/netI     0.0636
_diffrn_reflns_theta_min     2.95
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     26.50
_diffrn_measured_fraction_theta_max     0.957
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     7461
_reflns_number_gt     5387
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0952
_refine_ls_R_factor_gt     0.0560
_refine_ls_wR_factor_gt     0.1132
_refine_ls_wR_factor_ref     0.1286
_refine_ls_goodness_of_fit_ref     1.006
_refine_ls_restrained_S_all     1.006
_refine_ls_number_reflns     7461
_refine_ls_number_parameters     421
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refxyz
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0671P)²] 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     0.003
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.41
_refine_diff_density_min     -0.29
_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'
    'F' 'F' 0.0171 0.0103
                         '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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005) and SHELXTL-NT (Sheldrick,
2008)
;
_computing_publication_material     'SHELXL97 (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
    S S1 0.65033(8) 0.34420(5) 1.07733(5) 0.02187(15) Uani d . 1 . .
    C C11 0.4967(3) 0.2312(2) 1.01349(17) 0.0168(5) Uani d . 1 . .
    C C21 0.4187(3) 0.3087(2) 0.87042(17) 0.0160(5) Uani d . 1 . .
    N N11 0.4074(3) 0.22647(18) 0.92489(15) 0.0165(4) Uani d . 1 . .
    H H11 0.332(4) 0.160(3) 0.902(2) 0.020 Uiso d . 1 . .
    N N21 0.4466(3) 0.13422(19) 1.04580(17) 0.0195(4) Uani d . 1 . .
    H H211 0.378(4) 0.078(3) 1.012(2) 0.023 Uiso d . 1 . .
    H H221 0.501(4) 0.129(3) 1.100(2) 0.023 Uiso d . 1 . .
    N N31 0.3180(3) 0.2799(2) 0.78807(16) 0.0207(5) Uani d . 1 . .
    H H311 0.253(4) 0.211(3) 0.769(2) 0.025 Uiso d . 1 . .
    H H321 0.329(4) 0.327(3) 0.754(2) 0.025 Uiso d . 1 . .
    N N41 0.5254(3) 0.41215(19) 0.89735(18) 0.0224(5) Uani d . 1 . .
    H H411 0.582(4) 0.423(3) 0.948(2) 0.027 Uiso d . 1 . .
    H H421 0.520(4) 0.455(3) 0.862(2) 0.027 Uiso d . 1 . .
    S S2 0.58023(8) 0.77907(6) 0.56529(5) 0.02171(15) Uani d . 1 . .
    C C12 0.7568(3) 0.8815(2) 0.61651(17) 0.0165(5) Uani d . 1 . .
    C C22 0.8175(3) 0.8187(2) 0.77058(17) 0.0159(5) Uani d . 1 . .
    N N12 0.8497(3) 0.88734(18) 0.70460(15) 0.0161(4) Uani d . 1 . .
    H H12 0.935(4) 0.943(3) 0.717(2) 0.019 Uiso d . 1 . .
    N N22 0.8237(3) 0.9687(2) 0.57484(17) 0.0209(5) Uani d . 1 . .
    H H212 0.919(4) 1.017(3) 0.600(2) 0.025 Uiso d . 1 . .
    H H222 0.777(4) 0.967(3) 0.523(2) 0.025 Uiso d . 1 . .
    N N32 0.9254(3) 0.84630(19) 0.85032(16) 0.0199(4) Uani d . 1 . .
    H H312 1.015(4) 0.904(3) 0.856(2) 0.024 Uiso d . 1 . .
    H H322 0.916(4) 0.802(3) 0.889(2) 0.024 Uiso d . 1 . .
    N N42 0.6839(3) 0.72842(19) 0.75633(17) 0.0205(5) Uani d . 1 . .
    H H412 0.610(4) 0.715(3) 0.702(2) 0.025 Uiso d . 1 . .
    H H422 0.679(4) 0.693(3) 0.796(2) 0.025 Uiso d . 1 . .
    S S3 0.94092(8) 0.68826(6) 0.40442(5) 0.02431(16) Uani d . 1 . .
    C C13 0.8619(3) 0.6004(2) 0.47814(17) 0.0158(5) Uani d . 1 . .
    C C23 1.0729(3) 0.6814(2) 0.62613(17) 0.0151(5) Uani d . 1 . .
    N N13 0.9309(3) 0.60576(18) 0.57172(15) 0.0155(4) Uani d . 1 . .
    H H13 0.869(4) 0.554(3) 0.599(2) 0.019 Uiso d . 1 . .
    N N23 0.7215(3) 0.51430(18) 0.44971(17) 0.0180(4) Uani d . 1 . .
    H H213 0.681(4) 0.475(3) 0.491(2) 0.022 Uiso d . 1 . .
    H H223 0.664(4) 0.512(2) 0.396(2) 0.022 Uiso d . 1 . .
    N N33 1.1119(3) 0.6634(2) 0.71263(16) 0.0205(5) Uani d . 1 . .
    H H313 1.050(4) 0.613(3) 0.732(2) 0.025 Uiso d . 1 . .
    H H323 1.196(4) 0.713(3) 0.747(2) 0.025 Uiso d . 1 . .
    N N43 1.1657(3) 0.76801(19) 0.59415(18) 0.0216(5) Uani d . 1 . .
    H H413 1.139(4) 0.773(3) 0.535(2) 0.026 Uiso d . 1 . .
    H H423 1.248(4) 0.810(3) 0.631(2) 0.026 Uiso d . 1 . .
    S S4 0.89831(9) 0.13769(6) 0.91483(5) 0.02482(16) Uani d . 1 . .
    C C14 0.9121(3) 0.2595(2) 0.87298(17) 0.0176(5) Uani d . 1 . .
    C C24 0.6875(3) 0.1886(2) 0.73083(18) 0.0161(5) Uani d . 1 . .
    N N14 0.8184(3) 0.26871(18) 0.79072(15) 0.0175(4) Uani d . 1 . .
    H H14 0.838(4) 0.334(3) 0.779(2) 0.021 Uiso d . 1 . .
    N N24 1.0205(3) 0.35896(19) 0.91640(16) 0.0204(5) Uani d . 1 . .
    H H214 1.025(4) 0.421(3) 0.893(2) 0.024 Uiso d . 1 . .
    H H224 1.077(4) 0.359(3) 0.970(2) 0.024 Uiso d . 1 . .
    N N44 0.6221(3) 0.08607(19) 0.74982(17) 0.0206(5) Uani d . 1 . .
    H H314 0.667(4) 0.286(3) 0.642(2) 0.025 Uiso d . 1 . .
    H H324 0.547(4) 0.174(3) 0.618(2) 0.025 Uiso d . 1 . .
    N N34 0.6283(3) 0.2179(2) 0.65343(17) 0.0212(5) Uani d . 1 . .
    H H414 0.663(4) 0.066(3) 0.800(2) 0.025 Uiso d . 1 . .
    H H424 0.553(4) 0.046(3) 0.713(2) 0.025 Uiso d . 1 . .
    F F11 0.24069(19) -0.00178(12) 0.87552(11) 0.0228(3) Uani d . 1 . .
    F F21 0.37400(19) -0.11575(13) 0.77898(11) 0.0221(3) Uani d . 1 . .
    H H11F 0.318(4) -0.075(3) 0.820(2) 0.027 Uiso d . 1 . .
    F F12 0.12625(19) 0.06459(13) 0.69533(11) 0.0258(3) Uani d . 1 . .
    F F22 0.3311(2) 0.01618(13) 0.60668(11) 0.0243(3) Uani d . 1 . .
    H H12F 0.230(4) 0.037(3) 0.648(2) 0.029 Uiso d . 1 . .
    F F13 0.78898(19) 0.62194(12) 0.90490(11) 0.0227(3) Uani d . 1 . .
    F F23 0.92486(19) 0.50839(12) 0.81046(11) 0.0235(3) Uani d . 1 . .
    H H13F 0.866(4) 0.568(3) 0.860(2) 0.028 Uiso d . 1 . .
    F F14 0.68870(18) 0.44053(12) 0.62464(11) 0.0222(3) Uani d . 1 . .
    F F24 0.49078(19) 0.48832(12) 0.71916(10) 0.0217(3) Uani d . 1 . .
    H H14F 0.584(4) 0.469(3) 0.675(2) 0.026 Uiso d . 1 . .
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
    S1 C11 . 1.678(3) ?
    C11 N21 . 1.328(3) ?
    C11 N11 . 1.393(3) ?
    C21 N41 . 1.314(3) ?
    C21 N31 . 1.318(3) ?
    C21 N11 . 1.365(3) ?
    N11 H11 . 0.87(3) ?
    N21 H211 . 0.82(3) ?
    N21 H221 . 0.88(3) ?
    N31 H311 . 0.86(3) ?
    N31 H321 . 0.81(3) ?
    N41 H411 . 0.79(3) ?
    N41 H421 . 0.79(3) ?
    S2 C12 . 1.673(3) ?
    C12 N22 . 1.329(3) ?
    C12 N12 . 1.397(3) ?
    C22 N42 . 1.318(3) ?
    C22 N32 . 1.321(3) ?
    C22 N12 . 1.364(3) ?
    N12 H12 . 0.83(3) ?
    N22 H212 . 0.86(3) ?
    N22 H222 . 0.80(3) ?
    N32 H312 . 0.87(3) ?
    N32 H322 . 0.83(3) ?
    N42 H412 . 0.91(3) ?
    N42 H422 . 0.76(3) ?
    S3 C13 . 1.680(3) ?
    C13 N23 . 1.328(3) ?
    C13 N13 . 1.388(3) ?
    C23 N43 . 1.313(3) ?
    C23 N33 . 1.317(3) ?
    C23 N13 . 1.369(3) ?
    N13 H13 . 0.87(3) ?
    N23 H213 . 0.86(3) ?
    N23 H223 . 0.86(3) ?
    N33 H313 . 0.80(3) ?
    N33 H323 . 0.84(3) ?
    N43 H413 . 0.87(3) ?
    N43 H423 . 0.82(3) ?
    S4 C14 . 1.681(3) ?
    C14 N24 . 1.322(3) ?
    C14 N14 . 1.389(3) ?
    C24 N34 . 1.313(3) ?
    C24 N44 . 1.317(3) ?
    C24 N14 . 1.367(3) ?
    N14 H14 . 0.82(3) ?
    N24 H214 . 0.87(3) ?
    N24 H224 . 0.86(3) ?
    N44 H414 . 0.87(3) ?
    N44 H424 . 0.75(3) ?
    N34 H314 . 0.86(3) ?
    N34 H324 . 0.81(3) ?
    F11 H11F . 1.38(3) ?
    F21 H11F . 0.92(3) ?
    F12 H12F . 1.20(3) ?
    F22 H12F . 1.10(3) ?
    F13 H13F . 1.16(3) ?
    F23 H13F . 1.14(3) ?
    F14 H14F . 1.23(3) ?
    F24 H14F . 1.06(3) ?
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
    N21 C11 N11 . . 112.6(2) ?
    N21 C11 S1 . . 121.2(2) ?
    N11 C11 S1 . . 126.21(19) ?
    N41 C21 N31 . . 120.6(2) ?
    N41 C21 N11 . . 122.3(2) ?
    N31 C21 N11 . . 117.1(2) ?
    C21 N11 C11 . . 130.0(2) ?
    C21 N11 H11 . . 116.4(19) ?
    C11 N11 H11 . . 113.5(19) ?
    C11 N21 H211 . . 120(2) ?
    C11 N21 H221 . . 118(2) ?
    H211 N21 H221 . . 121(3) ?
    C21 N31 H311 . . 121(2) ?
    C21 N31 H321 . . 117(2) ?
    H311 N31 H321 . . 121(3) ?
    C21 N41 H411 . . 115(2) ?
    C21 N41 H421 . . 115(2) ?
    H411 N41 H421 . . 130(3) ?
    N22 C12 N12 . . 112.5(2) ?
    N22 C12 S2 . . 121.5(2) ?
    N12 C12 S2 . . 125.90(19) ?
    N42 C22 N32 . . 120.8(2) ?
    N42 C22 N12 . . 121.8(2) ?
    N32 C22 N12 . . 117.4(2) ?
    C22 N12 C12 . . 130.1(2) ?
    C22 N12 H12 . . 118(2) ?
    C12 N12 H12 . . 112(2) ?
    C12 N22 H212 . . 120(2) ?
    C12 N22 H222 . . 116(2) ?
    H212 N22 H222 . . 124(3) ?
    C22 N32 H312 . . 119(2) ?
    C22 N32 H322 . . 120(2) ?
    H312 N32 H322 . . 120(3) ?
    C22 N42 H412 . . 117.6(19) ?
    C22 N42 H422 . . 115(2) ?
    H412 N42 H422 . . 128(3) ?
    N23 C13 N13 . . 112.4(2) ?
    N23 C13 S3 . . 121.35(19) ?
    N13 C13 S3 . . 126.24(19) ?
    N43 C23 N33 . . 121.4(2) ?
    N43 C23 N13 . . 121.9(2) ?
    N33 C23 N13 . . 116.7(2) ?
    C23 N13 C13 . . 129.9(2) ?
    C23 N13 H13 . . 117.5(19) ?
    C13 N13 H13 . . 112.6(19) ?
    C13 N23 H213 . . 118(2) ?
    C13 N23 H223 . . 117(2) ?
    H213 N23 H223 . . 123(3) ?
    C23 N33 H313 . . 120(2) ?
    C23 N33 H323 . . 117(2) ?
    H313 N33 H323 . . 123(3) ?
    C23 N43 H413 . . 118(2) ?
    C23 N43 H423 . . 117(2) ?
    H413 N43 H423 . . 125(3) ?
    N24 C14 N14 . . 112.4(2) ?
    N24 C14 S4 . . 121.7(2) ?
    N14 C14 S4 . . 125.84(19) ?
    N34 C24 N44 . . 121.0(2) ?
    N34 C24 N14 . . 117.4(2) ?
    N44 C24 N14 . . 121.6(2) ?
    C24 N14 C14 . . 130.0(2) ?
    C24 N14 H14 . . 115(2) ?
    C14 N14 H14 . . 115(2) ?
    C14 N24 H214 . . 120(2) ?
    C14 N24 H224 . . 116(2) ?
    H214 N24 H224 . . 124(3) ?
    C24 N44 H414 . . 121(2) ?
    C24 N44 H424 . . 115(2) ?
    H414 N44 H424 . . 124(3) ?
    C24 N34 H314 . . 121(2) ?
    C24 N34 H324 . . 120(2) ?
    H314 N34 H324 . . 119(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
    F21 H11F F11 . 0.92(3) 1.38(3) 2.291(2) 172(3)
    F22 H12F F12 . 1.10(3) 1.20(3) 2.291(2) 177(3)
    F23 H13F F13 . 1.14(3) 1.16(3) 2.287(2) 172(3)
    F24 H14F F14 . 1.06(3) 1.23(3) 2.289(2) 177(3)
    N11 H11 F11 . 0.87(3) 1.89(3) 2.711(3) 157(3)
    N21 H211 F11 . 0.82(3) 2.10(3) 2.823(3) 148(3)
    N21 H221 F21 2_657 0.88(3) 2.00(3) 2.873(3) 179(3)
    N31 H311 F12 . 0.86(3) 1.90(3) 2.732(3) 166(3)
    N31 H321 F24 . 0.81(3) 2.24(3) 2.955(3) 147(3)
    N41 H421 F24 . 0.79(3) 2.14(3) 2.867(3) 152(3)
    N12 H12 F12 1_665 0.83(3) 1.96(3) 2.744(3) 159(3)
    N22 H212 F12 1_665 0.86(3) 1.99(3) 2.768(3) 151(3)
    N22 H222 F22 2_666 0.80(3) 2.05(3) 2.847(3) 173(3)
    N32 H312 F11 1_665 0.87(3) 1.89(3) 2.734(3) 165(3)
    N32 H322 F13 . 0.83(3) 2.24(3) 2.953(3) 144(3)
    N42 H422 F13 . 0.76(3) 2.16(3) 2.862(3) 153(3)
    N13 H13 F14 . 0.87(3) 1.87(3) 2.708(3) 162(3)
    N23 H213 F14 . 0.86(3) 2.01(3) 2.796(3) 151(3)
    N23 H223 F24 2_666 0.86(3) 1.99(3) 2.851(3) 173(3)
    N33 H323 F21 1_665 0.84(3) 2.18(3) 2.940(3) 150(3)
    N33 H313 F23 . 0.80(3) 1.98(3) 2.768(3) 166(3)
    N43 H423 F21 1_665 0.82(3) 2.20(3) 2.928(3) 149(3)
    N43 H423 F22 1_665 0.82(3) 2.53(3) 2.958(3) 114(3)
    N14 H14 F23 . 0.82(3) 2.02(3) 2.789(3) 156(3)
    N24 H214 F23 . 0.87(3) 1.99(3) 2.788(3) 151(3)
    N24 H224 F13 2_767 0.86(3) 1.96(3) 2.821(3) 174(3)
    N34 H324 F22 . 0.81(3) 2.24(3) 2.933(3) 145(3)
    N34 H314 F14 . 0.86(3) 1.92(3) 2.750(3) 163(3)
    N44 H424 F21 . 0.75(3) 2.52(3) 2.891(3) 112(3)
    N44 H424 F22 . 0.75(3) 2.19(3) 2.865(3) 151(3)
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
bis[1-(diaminomethylene)thiouron-1-ium]  hexafluoridosilicate
;
_chemical_formula_moiety     '2C2 H7 N4 S + , F6 Si 2-'
_chemical_formula_sum     'C4 H14 F6 N8 S2 Si'
_chemical_formula_iupac     '2C2 H7 N4 S + , Si F6 2-'
_chemical_formula_weight     380.44
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.537(3)
_cell_length_b     7.390(3)
_cell_length_c     7.884(4)
_cell_angle_alpha     83.65(3)
_cell_angle_beta     83.44(3)
_cell_angle_gamma     66.15(3)
_cell_volume     345.2(3)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     3979
_cell_measurement_theta_min     3.42
_cell_measurement_theta_max     36.71
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.830
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     194
_exptl_absorpt_coefficient_mu     0.549
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details     '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_absorpt_correction_T_min     0.870
_exptl_absorpt_correction_T_max     0.953
_exptl_special_details
;
IR spectra were collected on BRUKER spectrometer for samples suspended in nujol
mull (KBr windows). (2): 431.3 (w), 466.3 (w), 475.8 (w), 557.5 (w), 672.9
(m), 724.3 (m), 781.4 (w), 911.0 (vw), 990.8 (vw), 1103.8 (w),
1153.3 (w), 1180.6 (w), 1248.5 (m), 1341.1 (s), 1376.6
(s), 1462.6 (s), 1516.1 (m), 1611.3 (vs),
1711.5 (s), 2854.0 (vs), 2923.9 (vs), 3106.4
(s), 3241.6 (s), 3336.2 (s), 3423.6 (s)
;
_diffrn_ambient_temperature     100(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     'Oxford Diffraction KM4 CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4487
_diffrn_reflns_av_R_equivalents     0.0207
_diffrn_reflns_av_sigmaI/netI     0.0234
_diffrn_reflns_theta_min     3.42
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     26.50
_diffrn_measured_fraction_theta_max     0.911
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     7
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     1837
_reflns_number_gt     1582
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0332
_refine_ls_R_factor_gt     0.0260
_refine_ls_wR_factor_gt     0.0685
_refine_ls_wR_factor_ref     0.0712
_refine_ls_goodness_of_fit_ref     1.008
_refine_ls_restrained_S_all     1.008
_refine_ls_number_reflns     1837
_refine_ls_number_parameters     125
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0502P)²] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.38
_refine_diff_density_min     -0.28
_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'
    'F' 'F' 0.0171 0.0103
                         '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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Si' 'Si' 0.0817 0.0704
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005) and SHELXTL-NT (Sheldrick,
2008)
;
_computing_publication_material     'SHELXL97 (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
    Si Si1 0.0000 1.0000 0.0000 0.01013(12) Uani d S 1 . .
    F F1 0.24934(12) 0.95426(11) -0.11350(10) 0.01524(18) Uani d . 1 . .
    F F2 0.10377(12) 1.04449(11) 0.17299(10) 0.01523(18) Uani d . 1 . .
    F F3 0.08812(13) 0.75883(11) 0.06702(10) 0.01587(18) Uani d . 1 . .
    S S1 0.68023(5) 0.61828(5) 0.59622(4) 0.01390(10) Uani d . 1 . .
    C C1 0.4908(2) 0.76695(18) 0.46135(16) 0.0112(2) Uani d . 1 . .
    C C2 0.6659(2) 0.61699(19) 0.18499(16) 0.0112(2) Uani d . 1 . .
    N N1 0.51467(18) 0.76054(16) 0.28476(14) 0.0117(2) Uani d . 1 . .
    H H1 0.409(3) 0.847(3) 0.230(2) 0.019(4) Uiso d . 1 . .
    N N2 0.29919(18) 0.90823(17) 0.51676(15) 0.0136(2) Uani d . 1 . .
    H H21 0.204(3) 0.998(3) 0.451(3) 0.035(5) Uiso d . 1 . .
    H H22 0.272(2) 0.926(2) 0.623(2) 0.008(4) Uiso d . 1 . .
    N N3 0.6347(2) 0.63905(18) 0.02024(15) 0.0144(2) Uani d . 1 . .
    H H31 0.518(3) 0.734(3) -0.020(3) 0.037(6) Uiso d . 1 . .
    H H32 0.717(3) 0.537(3) -0.041(2) 0.028(5) Uiso d . 1 . .
    N N4 0.83427(19) 0.46546(17) 0.24824(16) 0.0135(2) Uani d . 1 . .
    H H41 0.849(4) 0.453(3) 0.363(3) 0.038(5) Uiso d . 1 . .
    H H42 0.906(3) 0.383(3) 0.190(2) 0.015(4) Uiso d . 1 . .
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
    Si1 F1 . 1.6911(11) yes
    Si1 F2 . 1.7086(10) yes
    Si1 F3 . 1.6788(11) yes
    Si1 F3 2_575 1.6789(10) ?
    Si1 F1 2_575 1.6911(11) ?
    Si1 F2 2_575 1.7086(10) ?
    S1 C1 . 1.6774(14) ?
    C1 N2 . 1.3296(18) ?
    C1 N1 . 1.3870(18) ?
    C2 N4 . 1.3113(17) ?
    C2 N3 . 1.3198(18) ?
    C2 N1 . 1.3711(18) ?
    N1 H1 . 0.848(18) ?
    N2 H21 . 0.87(2) ?
    N2 H22 . 0.848(17) ?
    N3 H31 . 0.86(2) ?
    N3 H32 . 0.89(2) ?
    N4 H41 . 0.91(2) ?
    N4 H42 . 0.763(19) ?
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
    F1 Si1 F2 . . 90.02(5) yes
    F3 Si1 F1 . . 89.77(5) yes
    F3 Si1 F2 . . 90.12(5) yes
    F3 Si1 F3 . 2_575 180.0 ?
    F3 Si1 F1 2_575 . 90.23(5) ?
    F3 Si1 F1 . 2_575 90.23(5) ?
    F3 Si1 F1 2_575 2_575 89.77(5) ?
    F1 Si1 F1 . 2_575 180.0 ?
    F3 Si1 F2 2_575 . 89.88(5) ?
    F1 Si1 F2 2_575 . 89.98(5) ?
    F3 Si1 F2 . 2_575 89.88(5) ?
    F3 Si1 F2 2_575 2_575 90.12(5) ?
    F1 Si1 F2 . 2_575 89.98(5) ?
    F1 Si1 F2 2_575 2_575 90.02(5) ?
    F2 Si1 F2 . 2_575 180.0 ?
    N2 C1 N1 . . 112.97(11) ?
    N2 C1 S1 . . 121.79(11) ?
    N1 C1 S1 . . 125.24(10) ?
    N4 C2 N3 . . 121.12(13) ?
    N4 C2 N1 . . 122.29(12) ?
    N3 C2 N1 . . 116.59(12) ?
    C2 N1 C1 . . 129.51(11) ?
    C2 N1 H1 . . 113.3(12) ?
    C1 N1 H1 . . 116.3(12) ?
    C1 N2 H21 . . 125.0(14) ?
    C1 N2 H22 . . 119.6(10) ?
    H21 N2 H22 . . 114.9(16) ?
    C2 N3 H31 . . 121.0(14) ?
    C2 N3 H32 . . 116.4(12) ?
    H31 N3 H32 . . 120.7(18) ?
    C2 N4 H41 . . 118.8(14) ?
    C2 N4 H42 . . 118.8(13) ?
    H41 N4 H42 . . 121.8(18) ?
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 F2 . 0.85(2) 2.01(2) 2.823(2) 162(2)
    N2 H22 F1 1_556 0.85(2) 2.10(2) 2.938(2) 173(2)
    N2 H21 F2 . 0.87(2) 2.31(2) 3.023(2) 139(2)
    N3 H31 F1 . 0.86(2) 2.00(2) 2.864(2) 179(2)
    N3 H32 F3 2_665 0.89(2) 2.05(2) 2.873(2) 153(2)
    N4 H42 F2 1_645 0.76(2) 2.32(2) 2.978(2) 146(2)
    N4 H42 F3 2_665 0.76(2) 2.38(2) 3.021(2) 143(2)
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-03-02
_journal_date_accepted     2009-03-24
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     o191
_journal_page_last     o194
_journal_paper_category     FO
_journal_coeditor_code     GD3281
_publ_contact_author_name     'Holynska, Malgorzata'
_publ_contact_author_address
;
Faculty of Chemistry
University of Wroclaw
14 Joliot-Curie Street
50-383 Wroclaw
Poland
;
_publ_contact_author_email     holynska@wcheto.chem.uni.wroc.pl
_publ_contact_author_phone     '+48605659593'
_publ_section_title
;
Products of the interaction of (1-diaminomethylene)thiourea with hydrofluoric
acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Hołyńska, Małgorzata'
;
Faculty of Chemistry
University of Wrocław
14 Joliot-Curie Street
50-383 Wrocław
Poland
;
    'Kubiak, Maria'
;
Faculty of Chemistry
University of Wrocław
14 Joliot-Curie Street
50-383 Wrocław
Poland
;
