#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/70/2017093.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2017093
loop_
_publ_author_name
'Hołyńska, Małgorzata'
'Kubiak, Maria'
_publ_section_title
;
 Products of the interaction of (1-diaminomethylene)thiourea with
 hydrofluoric acid
;
_journal_coeditor_code           GD3281
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o191
_journal_page_last               o194
_journal_paper_doi               10.1107/S0108270109010919
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C2 H7 N4 S + , H F2 -'
_chemical_formula_moiety         'C2 H7 N4 S + , F2 H -'
_chemical_formula_sum            'C2 H8 F2 N4 S'
_chemical_formula_weight         158.18
_chemical_name_systematic
;
1-(diaminomethylene)thiouron-1-ium hydrogen difluoride
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                100.78(3)
_cell_angle_beta                 93.87(3)
_cell_angle_gamma                104.50(3)
_cell_formula_units_Z            8
_cell_length_a                   8.199(3)
_cell_length_b                   12.203(4)
_cell_length_c                   14.158(4)
_cell_measurement_reflns_used    8334
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.79
_cell_measurement_theta_min      2.95
_cell_volume                     1337.5(8)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005) and SHELXTL-NT (Sheldrick,
2008)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Oxford Diffraction KM4 CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20685
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                5387
_reflns_number_total             7461
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3281.cif
_cod_data_source_block           I
_cod_database_code               2017093
_cod_database_fobs_code          2017093
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_
_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'
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_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_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)
