#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/24/4022444.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022444
loop_
_publ_author_name
'Franciszek S\;aczewski'
'Jaros\/law S\;aczewski'
'Maria Gdaniec'
_publ_section_title
;
 Synthesis, Molecular Structure, and Applications of
 2-Hydroxylamino-4,5-dihydroimidazolium-O-sulfonate to the
 Synthesis of Novel Heterocyclic Ring Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4791
_journal_page_last               4796
_journal_paper_doi               10.1021/jo034309n
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C5 H5 N3 S3'
_chemical_formula_weight         203.30
_chemical_melting_point          249.0(10)
_chemical_name_systematic
;
7,8-dihydroimidazo[1,2-c][1,3,5]thiadiazine-2,4(6H)-dithione
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 132.541(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.7501(13)
_cell_length_b                   6.1929(4)
_cell_length_c                   15.6134(9)
_cell_measurement_temperature    294(2)
_cell_volume                     1620.77(17)
_computing_cell_refinement       'KM4RED, Version 1.166, 2000'
_computing_data_collection       'KM4CCD, Version 1.166, 2000'
_computing_data_reduction        'KM4RED, Version 1.166, 2000'
_computing_molecular_graphics
;
Stereochemical Workstation, Siemens Analytical X-Ray Instruments, Inc., 1989.
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'KumaCCD diffractometer'
_diffrn_measurement_method       '\o 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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7234
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         3.51
_diffrn_standards_decay_%        <1.5
_diffrn_standards_interval_count 50
_exptl_absorpt_coefficient_mu    0.847
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0403
_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/[\s^2^(Fo^2^)+(0.0596P)^2^+0.6951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                1754
_reflns_number_total             1926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034309nsi20030314_024222_3.cif
_cod_data_source_block           cmpd15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '248-250' was changed to '249.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022444
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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
S1 S 0.04872(4) 0.52749(11) -0.10824(5) 0.0571(2) Uani 1 1 d
S2 S 0.25727(3) 0.40501(10) 0.38609(5) 0.0597(2) Uani 1 1 d
N1 N 0.05839(9) 0.7643(3) 0.04080(13) 0.0395(4) Uani 1 1 d
C2 C 0.08279(11) 0.5897(3) 0.02154(17) 0.0396(4) Uani 1 1 d
S3 S 0.15293(3) 0.40576(8) 0.13342(5) 0.04831(18) Uani 1 1 d
C4 C 0.18508(11) 0.5223(3) 0.26086(17) 0.0409(4) Uani 1 1 d
N5 N 0.14862(8) 0.7070(3) 0.25008(12) 0.0381(3) Uani 1 1 d
C6 C 0.16750(12) 0.8221(4) 0.34868(17) 0.0446(4) Uani 1 1 d
C7 C 0.10304(14) 0.9953(4) 0.28973(19) 0.0508(5) Uani 1 1 d
N8 N 0.06398(10) 0.9780(3) 0.16800(15) 0.0443(4) Uani 1 1 d
C9 C 0.08815(10) 0.8127(3) 0.14625(15) 0.0361(4) Uani 1 1 d
H6A H 0.1658(14) 0.726(4) 0.397(2) 0.062(7) Uiso 1 1 d
H6B H 0.2167(15) 0.890(4) 0.391(2) 0.059(7) Uiso 1 1 d
H7A H 0.1267(16) 1.137(5) 0.323(2) 0.064(7) Uiso 1 1 d
H7B H 0.0637(15) 0.960(4) 0.296(2) 0.065(7) Uiso 1 1 d
H8 H 0.0292(16) 1.050(4) 0.114(2) 0.056(7) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0699(4) 0.0616(4) 0.0463(3) -0.0026(2) 0.0418(3) 0.0012(3)
S2 0.0516(3) 0.0545(4) 0.0482(3) 0.0189(2) 0.0238(3) 0.0203(2)
N1 0.0396(7) 0.0418(8) 0.0339(7) 0.0078(6) 0.0235(7) 0.0077(6)
C2 0.0369(9) 0.0413(10) 0.0412(9) 0.0043(7) 0.0267(8) 0.0002(7)
S3 0.0526(3) 0.0408(3) 0.0496(3) 0.0068(2) 0.0338(3) 0.0114(2)
C4 0.0376(9) 0.0387(10) 0.0440(10) 0.0098(8) 0.0266(8) 0.0061(7)
N5 0.0349(7) 0.0411(8) 0.0305(7) 0.0083(6) 0.0190(6) 0.0070(6)
C6 0.0444(10) 0.0511(12) 0.0341(9) 0.0042(8) 0.0249(8) 0.0047(9)
C7 0.0527(12) 0.0562(13) 0.0391(11) 0.0026(9) 0.0292(10) 0.0117(10)
N8 0.0447(9) 0.0453(10) 0.0350(8) 0.0091(7) 0.0238(7) 0.0140(7)
C9 0.0350(8) 0.0361(9) 0.0338(8) 0.0069(7) 0.0218(7) 0.0039(7)
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'
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
C9 N1 C2 121.42(15)
N1 C2 S1 122.79(14)
N1 C2 S3 122.17(14)
S1 C2 S3 115.04(11)
C4 S3 C2 105.22(9)
N5 C4 S2 123.77(15)
N5 C4 S3 117.26(14)
S2 C4 S3 118.97(12)
C4 N5 C9 125.62(16)
C4 N5 C6 123.89(15)
C9 N5 C6 110.49(15)
N5 C6 C7 103.18(15)
N5 C6 H6A 112.2(15)
C7 C6 H6A 111.6(14)
N5 C6 H6B 108.9(15)
C7 C6 H6B 108.3(16)
H6A C6 H6B 112(2)
N8 C7 C6 102.99(16)
N8 C7 H7A 113.0(16)
C6 C7 H7A 110.5(16)
N8 C7 H7B 108.6(15)
C6 C7 H7B 110.6(15)
H7A C7 H7B 111(2)
C9 N8 C7 113.72(16)
C9 N8 H8 117.4(19)
C7 N8 H8 128.8(19)
N8 C9 N1 123.23(16)
N8 C9 N5 108.86(16)
N1 C9 N5 127.90(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.653(2)
S2 C4 1.6450(19)
N1 C9 1.323(2)
N1 C2 1.339(2)
C2 S3 1.7679(19)
S3 C4 1.746(2)
C4 N5 1.354(2)
N5 C9 1.391(2)
N5 C6 1.473(2)
C6 C7 1.524(3)
C6 H6A 0.98(3)
C6 H6B 0.93(3)
C7 N8 1.459(3)
C7 H7A 0.97(3)
C7 H7B 0.99(3)
N8 C9 1.311(3)
N8 H8 0.79(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N8 H8 N1 0.79(3) 2.15(3) 2.942(2) 172(3) 5_575
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9085872
2 PubChem 135405394
