#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/70/2017002.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_2017002
loop_
_publ_author_name
'Janczak, Jan'
'Perpétuo, Genivaldo Julio'
_publ_section_title
;
 Two-dimensional hydrogen-bonded networks in
 1-(diaminomethylene)thiouron-1-ium nitrate and
 bis[1-(diaminomethylene)thiouron-1-ium] phosphonate monohydrate
;
_journal_coeditor_code           FG3078
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o118
_journal_page_last               o120
_journal_paper_doi               10.1107/S0108270109006325
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2C2 H7 N4 S +, H P O3 2-, H2 O'
_chemical_formula_moiety         '2(C2 H7 N4 S +), H O3 P 2-, H2 O'
_chemical_formula_sum            'C4 H17 N8 O4 P S2'
_chemical_formula_weight         336.35
_chemical_name_systematic
;
bis[1-(diaminomethylene)thiouron-1-ium] phosphonate monohydrate
;
_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           SHELXL-97
_cell_angle_alpha                72.700(16)
_cell_angle_beta                 72.961(15)
_cell_angle_gamma                85.842(14)
_cell_formula_units_Z            2
_cell_length_a                   7.6109(12)
_cell_length_b                   7.8771(14)
_cell_length_c                   12.758(2)
_cell_measurement_reflns_used    852
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.53
_cell_measurement_theta_min      2.85
_cell_volume                     698.1(2)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_molecular_graphics
;
Diamond (Brandenburg & Putz, 2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Kuma KM-4 with area CCD detector'
_diffrn_measurement_method       ω-scan
_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  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0869
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8542
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         29.53
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.9231
_exptl_absorpt_correction_T_min  0.8502
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      1.594
_exptl_crystal_density_method    floatation
_exptl_crystal_description       paralellepiped
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0280P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0885
_reflns_number_gt                1950
_reflns_number_total             3529
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3078.cif
_cod_data_source_block           II
_cod_database_code               2017002
_cod_database_fobs_code          2017002
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
P P1 0.37123(9) 0.14677(9) 0.64056(6) 0.02563(18) Uani d . 1 . .
H H1 0.430(3) 0.146(3) 0.5294(18) 0.017(6) Uiso d . 1 . .
O O1 0.3364(2) 0.3387(2) 0.63694(17) 0.0362(5) Uani d . 1 . .
O O2 0.1971(2) 0.0318(2) 0.69163(16) 0.0331(5) Uani d . 1 . .
O O3 0.5187(2) 0.0705(2) 0.69932(16) 0.0338(5) Uani d . 1 . .
S S11 0.22758(10) -0.45085(10) 1.07379(7) 0.0407(2) Uani d . 1 . .
C C11 0.2605(4) -0.2956(3) 0.9465(2) 0.0306(7) Uani d . 1 . .
N N11 0.1256(3) -0.1898(3) 0.90960(19) 0.0301(6) Uani d D 1 . .
H H11 0.1540 -0.1260 0.8385 0.036 Uiso d D 1 . .
N N12 0.4235(3) -0.2654(3) 0.8699(2) 0.0410(7) Uani d . 1 . .
H H121 0.4364 -0.1862 0.8049 0.049 Uiso calc R 1 . .
H H122 0.5168 -0.3250 0.8850 0.049 Uiso calc R 1 . .
C C12 -0.0556(4) -0.1779(3) 0.9673(2) 0.0301(7) Uani d . 1 . .
N N14 -0.1252(3) -0.2582(3) 1.0754(2) 0.0443(7) Uani d . 1 . .
H H141 -0.2384 -0.2428 1.1089 0.053 Uiso calc R 1 . .
H H142 -0.0581 -0.3269 1.1136 0.053 Uiso calc R 1 . .
N N13 -0.1568(3) -0.0726(3) 0.9080(2) 0.0442(7) Uani d . 1 . .
H H131 -0.2702 -0.0564 0.9408 0.053 Uiso calc R 1 . .
H H132 -0.1096 -0.0199 0.8364 0.053 Uiso calc R 1 . .
S S21 -0.15934(10) 0.79949(9) 0.64775(7) 0.0371(2) Uani d . 1 . .
C C21 0.0111(3) 0.6542(3) 0.6403(2) 0.0253(6) Uani d . 1 . .
N N21 -0.0014(3) 0.4810(3) 0.63714(19) 0.0243(5) Uani d D 1 . .
H H21 0.1010 0.4230 0.6310 0.029 Uiso d D 1 . .
N N22 0.1791(3) 0.6955(3) 0.6381(2) 0.0396(7) Uani d . 1 . .
H H221 0.2644 0.6178 0.6350 0.048 Uiso calc R 1 . .
H H222 0.2022 0.7998 0.6397 0.048 Uiso calc R 1 . .
C C22 -0.1487(3) 0.3912(3) 0.6396(2) 0.0199(6) Uani d . 1 . .
N N24 -0.3072(3) 0.4674(3) 0.6383(2) 0.0347(6) Uani d . 1 . .
H H241 -0.3976 0.4077 0.6385 0.042 Uiso calc R 1 . .
H H242 -0.3209 0.5772 0.6372 0.042 Uiso calc R 1 . .
N N23 -0.1257(3) 0.2238(3) 0.64123(18) 0.0294(6) Uani d . 1 . .
H H231 -0.2153 0.1629 0.6415 0.035 Uiso calc R 1 . .
H H232 -0.0212 0.1750 0.6421 0.035 Uiso calc R 1 . .
O O4W 0.5009(3) 0.1613(3) 0.89006(19) 0.0471(6) Uani d D 1 . .
H H1W 0.5500 0.2580 0.8750 0.071 Uiso d D 1 . .
H H2W 0.5070 0.1360 0.8310 0.071 Uiso d 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'
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'
P P 0.1023 0.0942 '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
O1 P1 O3 . . 111.38(11) ?
O1 P1 O2 . . 113.20(10) ?
O3 P1 O2 . . 111.99(10) ?
O1 P1 H1 . . 105.4(8) ?
O3 P1 H1 . . 109.6(9) ?
O2 P1 H1 . . 104.7(9) ?
N12 C11 N11 . . 113.0(2) ?
N12 C11 S11 . . 121.8(2) ?
N11 C11 S11 . . 125.2(2) ?
C12 N11 C11 . . 129.3(2) ?
C12 N11 H11 . . 113.4 ?
C11 N11 H11 . . 117.2 ?
C11 N12 H121 . . 120.0 ?
C11 N12 H122 . . 120.0 ?
H121 N12 H122 . . 120.0 ?
N14 C12 N13 . . 120.6(3) ?
N14 C12 N11 . . 123.2(3) ?
N13 C12 N11 . . 116.2(3) ?
C12 N14 H141 . . 120.0 ?
C12 N14 H142 . . 120.0 ?
H141 N14 H142 . . 120.0 ?
C12 N13 H131 . . 120.0 ?
C12 N13 H132 . . 120.0 ?
H131 N13 H132 . . 120.0 ?
N22 C21 N21 . . 112.2(2) ?
N22 C21 S21 . . 121.7(2) ?
N21 C21 S21 . . 126.02(19) ?
C22 N21 C21 . . 129.4(2) ?
C22 N21 H21 . . 115.7 ?
C21 N21 H21 . . 114.9 ?
C21 N22 H221 . . 120.0 ?
C21 N22 H222 . . 120.0 ?
H221 N22 H222 . . 120.0 ?
N24 C22 N23 . . 120.7(2) ?
N24 C22 N21 . . 122.1(2) ?
N23 C22 N21 . . 117.2(2) ?
C22 N24 H241 . . 120.0 ?
C22 N24 H242 . . 120.0 ?
H241 N24 H242 . . 120.0 ?
C22 N23 H231 . . 120.0 ?
C22 N23 H232 . . 120.0 ?
H231 N23 H232 . . 120.0 ?
H1W O4W H2W . . 111 ?
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
P1 O1 . 1.5051(18) ?
P1 O3 . 1.5195(19) ?
P1 O2 . 1.5226(18) ?
P1 H1 . 1.36(2) ?
S11 C11 . 1.679(3) ?
C11 N12 . 1.321(3) ?
C11 N11 . 1.376(3) ?
N11 C12 . 1.372(3) ?
N11 H11 . 0.8700 ?
N12 H121 . 0.8600 ?
N12 H122 . 0.8600 ?
C12 N14 . 1.298(3) ?
C12 N13 . 1.315(3) ?
N14 H141 . 0.8600 ?
N14 H142 . 0.8600 ?
N13 H131 . 0.8600 ?
N13 H132 . 0.8600 ?
S21 C21 . 1.667(3) ?
C21 N22 . 1.332(3) ?
C21 N21 . 1.388(3) ?
N21 C22 . 1.357(3) ?
N21 H21 . 0.8700 ?
N22 H221 . 0.8600 ?
N22 H222 . 0.8600 ?
C22 N24 . 1.311(3) ?
C22 N23 . 1.312(3) ?
N24 H241 . 0.8600 ?
N24 H242 . 0.8600 ?
N23 H231 . 0.8600 ?
N23 H232 . 0.8600 ?
O4W H1W . 0.8200 ?
O4W H2W . 0.8200 ?
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
N11 H11 O2 . 0.87 1.87 2.728(3) 173 y
N12 H121 O3 . 0.86 2.09 2.862(3) 149 y
N12 H122 S11 2_647 0.86 2.59 3.444(2) 170 y
N14 H141 O4W 2_557 0.86 2.05 2.846(3) 153 y
N14 H142 S11 . 0.86 2.30 2.984(3) 137 y
N13 H131 O4W 2_557 0.86 2.31 3.037(3) 142 y
N13 H131 O4W 1_455 0.86 2.44 3.104(3) 134 y
N13 H132 O2 . 0.86 2.49 3.188(3) 139 y
N21 H21 O1 . 0.87 1.88 2.729(3) 165 y
N22 H221 O1 . 0.86 2.22 2.976(3) 146 y
N22 H222 O2 1_565 0.86 2.12 2.948(3) 163 y
N24 H241 O1 1_455 0.86 2.14 2.970(3) 162 y
N24 H242 S21 . 0.86 2.27 2.969(2) 139 y
N23 H231 O3 1_455 0.86 2.05 2.846(3) 154 y
N23 H231 S21 1_545 0.86 2.84 3.345(2) 119 y
N23 H232 O2 . 0.86 2.09 2.923(3) 164 y
O4W H1W S11 2_657 0.82 2.68 3.399(2) 147 y
O4W H2W O3 . 0.82 1.88 2.698(3) 178 y
