#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226802.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_2226802
loop_
_publ_author_name
'Chen, Xiao-tao'
'Xu, Liang-zhong'
_publ_section_title
;
 (Z)-2-(1,3-Thiazolidin-2-ylidene)cyanamide
;
_journal_coeditor_code           BV2145
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2148
_journal_paper_doi               10.1107/S160053681002917X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C4 H5 N3 S'
_chemical_formula_moiety         'C4 H5 N3 S'
_chemical_formula_sum            'C4 H5 N3 S'
_chemical_formula_weight         127.18
_chemical_name_systematic
;
(Z)-2-(1,3-Thiazolidin-2-ylidene)cyanamide
;
_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                83.28(3)
_cell_angle_beta                 81.53(3)
_cell_angle_gamma                82.12(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4556(13)
_cell_length_b                   6.5584(13)
_cell_length_c                   6.7910(14)
_cell_measurement_reflns_used    916
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.3871
_cell_measurement_theta_min      3.0475
_cell_volume                     280.32(10)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'Crystalclear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1570
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.8984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             130
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.365
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0574P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                865
_reflns_number_total             968
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2145.cif
_cod_data_source_block           I
_cod_database_code               2226802
_cod_database_fobs_code          2226802
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 0.19920(8) 0.40549(8) 0.26592(8) 0.0167(3) Uani d . 1 . .
N N1 0.4033(3) 0.7184(3) 0.2385(3) 0.0161(4) Uani d . 1 . .
H H1C 0.5069 0.7914 0.2164 0.019 Uiso calc R 1 . .
N N2 0.6225(3) 0.4094(3) 0.2613(3) 0.0158(5) Uani d . 1 . .
N N3 0.6775(3) 0.0290(3) 0.2589(3) 0.0234(5) Uani d . 1 . .
C C1 0.0574(4) 0.6574(3) 0.2008(4) 0.0184(5) Uani d . 1 . .
H H1A 0.0483 0.6789 0.0584 0.022 Uiso calc R 1 . .
H H1B -0.0843 0.6700 0.2732 0.022 Uiso calc R 1 . .
C C2 0.1853(4) 0.8129(3) 0.2610(4) 0.0187(5) Uani d . 1 . .
H H2A 0.1700 0.9417 0.1752 0.022 Uiso calc R 1 . .
H H2B 0.1384 0.8415 0.3985 0.022 Uiso calc R 1 . .
C C3 0.4340(4) 0.5138(3) 0.2539(3) 0.0139(5) Uani d . 1 . .
C C4 0.6407(3) 0.2063(3) 0.2601(3) 0.0166(5) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0153(4) 0.0143(4) 0.0224(4) -0.0053(2) -0.0049(2) -0.0020(2)
N1 0.0159(10) 0.0126(10) 0.0221(11) -0.0057(7) -0.0056(8) -0.0021(7)
N2 0.0160(10) 0.0118(10) 0.0211(11) -0.0035(7) -0.0050(8) -0.0022(7)
N3 0.0211(11) 0.0139(11) 0.0358(13) -0.0013(8) -0.0083(9) -0.0013(8)
C1 0.0154(11) 0.0183(12) 0.0227(13) -0.0004(9) -0.0065(9) -0.0034(9)
C2 0.0200(12) 0.0145(12) 0.0221(13) -0.0003(9) -0.0050(9) -0.0039(9)
C3 0.0192(11) 0.0144(11) 0.0096(11) -0.0054(9) -0.0031(9) -0.0018(8)
C4 0.0126(11) 0.0220(13) 0.0166(12) -0.0041(9) -0.0053(9) -0.0008(9)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 S1 C1 . . 91.15(10) ?
C3 N1 C2 . . 116.32(19) ?
C3 N1 H1C . . 121.8 ?
C2 N1 H1C . . 121.8 ?
C3 N2 C4 . . 117.9(2) ?
C2 C1 S1 . . 105.21(16) ?
C2 C1 H1A . . 110.7 ?
S1 C1 H1A . . 110.7 ?
C2 C1 H1B . . 110.7 ?
S1 C1 H1B . . 110.7 ?
H1A C1 H1B . . 108.8 ?
N1 C2 C1 . . 106.10(17) ?
N1 C2 H2A . . 110.5 ?
C1 C2 H2A . . 110.5 ?
N1 C2 H2B . . 110.5 ?
C1 C2 H2B . . 110.5 ?
H2A C2 H2B . . 108.7 ?
N2 C3 N1 . . 122.1(2) ?
N2 C3 S1 . . 125.53(17) ?
N1 C3 S1 . . 112.34(17) ?
N3 C4 N2 . . 173.3(2) ?
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 C3 . 1.747(2) ?
S1 C1 . 1.816(2) ?
N1 C3 . 1.323(3) ?
N1 C2 . 1.452(3) ?
N1 H1C . 0.8600 ?
N2 C3 . 1.317(3) ?
N2 C4 . 1.321(3) ?
N3 C4 . 1.155(3) ?
C1 C2 . 1.522(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
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 H1C N3 1_565 0.86 2.10 2.903(3) 156.0
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 S1 C1 C2 . . . . -23.42(16) ?
C3 N1 C2 C1 . . . . -25.8(3) ?
S1 C1 C2 N1 . . . . 30.4(2) ?
C4 N2 C3 N1 . . . . -174.6(2) ?
C4 N2 C3 S1 . . . . 6.3(3) ?
C2 N1 C3 N2 . . . . -171.4(2) ?
C2 N1 C3 S1 . . . . 7.9(2) ?
C1 S1 C3 N2 . . . . -170.6(2) ?
C1 S1 C3 N1 . . . . 10.19(17) ?
C3 N2 C4 N3 . . . . 177(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2932524
