#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/94/2009445.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_2009445
loop_
_publ_author_name
'Cousson, A.'
'Nectoux, F.'
'Bachet, B.'
'Kokel, B.'
'Hubert-Habart, M.'
_publ_section_title
;Structure of
 5-[(1-amidiniohydrazono)ethyl]-4-methyl-2-methylthio-3H⁺-pyrimidinium
 dichloride hydrate, C₁₉H₁₆N₆S²⁺.2Cl^{-^}.H₂O
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              286
_journal_page_last               289
_journal_paper_doi               10.1107/S0108270193006638
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C9 H16 N6 S1 2+ , 2Cl 1- , H2 O1'
_chemical_formula_sum            'C9 H18 Cl2 N6 O S'
_chemical_formula_weight         329.25
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                67.37(4)
_cell_angle_beta                 71.67(6)
_cell_angle_gamma                75.93(6)
_cell_formula_units_Z            2
_cell_length_a                   7.652(7)
_cell_length_b                   10.481(5)
_cell_length_c                   11.076(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      25.04
_cell_volume                     770.7(10)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2694
_diffrn_reflns_theta_max         66
_diffrn_standards_decay_%        <1.2
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    5.1
_exptl_absorpt_correction_T_max  1.698
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.42
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.69
_refine_ls_extinction_coef       15.9(9)
_refine_ls_extinction_method     'Larson (1970)'
_refine_ls_goodness_of_fit_obs   0.92
_refine_ls_hydrogen_treatment    'refU (one U~eq~ for all H atoms)'
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2431
_refine_ls_R_factor_obs          0.073
_refine_ls_shift/esd_max         0.11
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.079
_reflns_number_observed          2431
_reflns_number_total             2685
_reflns_observed_criterion       I>=3\s(I)
_cod_data_source_file            du1034.cif
_cod_data_source_block           du1034_structure_1_of_1
_cod_original_cell_volume        771.0(10)
_cod_original_formula_sum        'C9 H18 Cl2 N6 O1 S1'
_cod_database_code               2009445
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
Cl(1) .0531(2) .73280(10) .8661(2) .0528
Cl(2) -.5251(2) .1886(2) .6046(2) .0513
S(1) .4216(2) .8511(2) -.0067(2) .0444
C(1) -.0373(7) .0812(5) .6153(5) .0291
C(2) -.0467(7) .4202(5) .3828(5) .0286
C(3) -.2458(9) .4585(6) .3825(7) .0500
C(4) .0816(7) .5226(5) .2935(5) .0275
C(5) .2704(7) .4898(5) .2407(5) .0296
C(6) .3812(8) .3480(6) .2681(6) .0428
C(7) .2829(7) .7303(5) .1144(5) .0318
C(8) .2493(9) .9977(6) -.0497(6) .0475
C(9) .0089(7) .6646(5) .2522(5) .0331
N(1) .1375(7) .0443(5) .6196(5) .0404
N(2) -.1614(7) -.0056(5) .6836(5) .0406
N(3) -.0995(6) .2094(4) .5379(4) .0334
N(4) .0239(6) .3023(4) .4573(4) .0303
N(5) .3655(6) .5964(4) .1534(4) .0336
N(6) .1056(6) .7674(4) .1650(4) .0341
O(1) .7243(6) .5540(5) .0331(5) .0574
H(3) -.2354 .2313 .5397 .061(5)
H(5) .4954 .5691 .1158 .061(5)
H(9) -.1329 .7050 .2839 .061(5)
H(11) .2229 .1088 .5931 .061(5)
H(12) .1663 -.0397 .6928 .061(5)
H(21) -.2900 .0244 .6772 .061(5)
H(22) -.1233 -.0916 .7433 .061(5)
H(31) -.3104 .3819 .3897 .061(5)
H(32) -.2721 .5309 .3031 .061(5)
H(33) -.2883 .4950 .4322 .061(5)
H(61) .3029 .2831 .2683 .061(5)
H(62) .4038 .3109 .3681 .061(5)
H(63) .5071 .3491 .2064 .061(5)
H(81) .2967 1.0563 -.1139 .061(5)
H(82) .1700 1.0278 .0281 .061(5)
H(83) .1533 .9763 -.0767 .061(5)
H(101) .8167 .6222 -.0133 .061(5)
H(102) .7929 .4722 .0564 .061(5)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(8) S(1) C(7) 100.3(3) yes
N(2) C(1) N(1) 121.9(5) yes
N(3) C(1) N(1) 121.8(5) yes
N(3) C(1) N(2) 116.3(5) yes
C(4) C(2) C(3) 118.6(5) yes
N(4) C(2) C(3) 124.4(5) yes
N(4) C(2) C(4) 117.1(5) yes
C(5) C(4) C(2) 125.2(5) yes
C(9) C(4) C(2) 118.5(5) yes
C(9) C(4) C(5) 116.2(4) yes
C(6) C(5) C(4) 126.9(5) yes
N(5) C(5) C(4) 117.5(5) yes
N(5) C(5) C(6) 115.7(4) yes
N(5) C(7) S(1) 116.5(4) yes
N(6) C(7) S(1) 121.4(4) yes
N(6) C(7) N(5) 122.2(5) yes
N(6) C(9) C(4) 125.1(5) yes
N(4) N(3) C(1) 119.6(4) yes
N(3) N(4) C(2) 115.3(4) yes
C(7) N(5) C(5) 122.6(4) yes
C(9) N(6) C(7) 116.4(4) yes
N(2) Cl(1) N(1) 40.80(10) no
O(1) Cl(1) N(1) 140.20(10) no
O(1) Cl(1) N(2) 99.40(10) no
O(1) Cl(1) N(1) 136.70(10) no
O(1) Cl(1) N(2) 161.20(10) no
O(1) Cl(1) O(1) 80.20(10) no
N(2) Cl(2) N(1) 118.70(10) no
N(3) Cl(2) N(1) 152.10(10) no
N(3) Cl(2) N(2) 42.10(10) no
Cl(1) O(1) Cl(1) 99.80(10) no
S(1) O(1) Cl(1) 89.30(10) no
S(1) O(1) Cl(1) 167.2(2) no
C(5) O(1) Cl(1) 88.30(10) no
C(5) O(1) Cl(1) 92.6(2) no
C(5) O(1) S(1) 96.6(2) no
C(6) O(1) Cl(1) 84.60(10) no
C(6) O(1) Cl(1) 118.5(2) no
C(6) O(1) S(1) 71.00(10) no
C(6) O(1) C(5) 25.90(10) no
C(7) O(1) Cl(1) 117.8(2) no
C(7) O(1) Cl(1) 139.5(2) no
C(7) O(1) S(1) 29.25(9) no
C(7) O(1) C(5) 102.5(2) no
C(7) O(1) C(6) 81.6(2) no
N(5) O(1) Cl(1) 137.8(2) no
N(5) O(1) Cl(1) 119.0(2) no
N(5) O(1) S(1) 50.00(10) no
N(5) O(1) C(5) 104.6(2) no
N(5) O(1) C(6) 90.3(2) no
N(5) O(1) C(7) 20.70(10) no
N(5) O(1) Cl(1) 110.8(2) no
N(5) O(1) Cl(1) 81.70(10) no
N(5) O(1) S(1) 103.6(2) no
N(5) O(1) C(5) 23.70(10) no
N(5) O(1) C(6) 42.00(10) no
N(5) O(1) C(7) 97.4(2) no
H(102) O(1) H(101) 104.2(4) no
H(31) C(3) C(2) 116.1(5) no
H(32) C(3) C(2) 115.1(6) no
H(32) C(3) H(31) 102.3(6) no
H(33) C(3) C(2) 105.7(6) no
H(33) C(3) H(31) 116.9(7) no
H(33) C(3) H(32) 99.9(6) no
H(61) C(6) C(5) 107.1(5) no
H(62) C(6) C(5) 110.0(5) no
H(62) C(6) H(61) 106.4(5) no
H(63) C(6) C(5) 111.8(5) no
H(63) C(6) H(61) 116.1(6) no
H(63) C(6) H(62) 105.2(5) no
H(81) C(8) S(1) 108.7(6) no
H(82) C(8) S(1) 114.3(5) no
H(82) C(8) H(81) 116.4(7) no
H(83) C(8) S(1) 112.4(5) no
H(83) C(8) H(81) 105.1(6) no
H(83) C(8) H(82) 99.4(6) no
H(9) C(9) C(4) 124.5(5) no
H(9) C(9) N(6) 110.4(5) no
H(11) N(1) C(1) 124.0(5) no
H(12) N(1) C(1) 116.8(5) no
H(12) N(1) H(11) 111.2(4) no
H(21) N(2) C(1) 120.0(5) no
H(22) N(2) C(1) 117.4(5) no
H(22) N(2) H(21) 122.3(5) no
H(3) N(3) C(1) 117.7(4) no
H(3) N(3) N(4) 122.6(4) no
H(5) N(5) C(5) 115.0(4) no
H(5) N(5) C(7) 122.2(4) no
H(102) O(1) H(101) 104.2(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) C(7) 1.726(5) yes
S(1) C(8) 1.781(6) yes
C(1) N(1) 1.310(7) yes
C(1) N(2) 1.319(6) yes
C(1) N(3) 1.351(6) yes
C(2) C(3) 1.479(8) yes
C(2) C(4) 1.476(7) yes
C(2) N(4) 1.293(6) yes
C(4) C(5) 1.389(7) yes
C(4) C(9) 1.403(7) yes
C(5) C(6) 1.491(7) yes
C(5) N(5) 1.354(6) yes
C(7) N(5) 1.353(7) yes
C(7) N(6) 1.319(7) yes
C(9) N(6) 1.333(6) yes
N(3) N(4) 1.373(6) yes
Cl(1) N(1) 3.404(5) no
Cl(1) N(2) 3.152(5) no
Cl(1) O(1) 3.156(5) no
Cl(1) O(1) 3.052(4) no
Cl(2) N(1) 3.227(5) no
Cl(2) N(2) 3.173(5) no
Cl(2) N(3) 3.148(4) no
O(1) H(101) 1.004(4) no
O(1) H(102) 0.880(4) no
C(3) H(31) 1.007(6) no
C(3) H(32) 0.956(6) no
C(3) H(33) 0.738(7) no
C(6) H(61) 1.008(6) no
C(6) H(62) 1.078(6) no
C(6) H(63) 0.990(6) no
C(8) H(81) 0.790(6) no
C(8) H(82) 0.999(6) no
C(8) H(83) 0.974(6) no
C(9) H(9) 1.064(5) no
N(1) H(11) 0.954(4) no
N(1) H(12) 0.975(4) no
N(2) H(21) 0.974(5) no
N(2) H(22) 0.932(4) no
N(3) H(3) 1.005(4) no
N(5) H(5) 0.968(4) no
O(1) H(101) 1.004(4) no
O(1) H(102) 0.880(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057028
