#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/70/2227021.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_2227021
loop_
_publ_author_name
'Li, Hong-xin'
'Zhang, Xiao-jun'
'Xu, Liang-zhong'
_publ_section_title
;
 (Z)-N-{3-[1-(4-Chlorophenyl)ethyl]thiazolidin-2-ylidene}cyanamide
;
_journal_coeditor_code           NG5002
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2171
_journal_paper_doi               10.1107/S1600536810029879
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H12 Cl N3 S'
_chemical_formula_moiety         'C12 H12 Cl N3 S'
_chemical_formula_sum            'C12 H12 Cl N3 S'
_chemical_formula_weight         265.76
_chemical_name_systematic
;
(Z)-N-{3-[1-(4-Chlorophenyl)ethyl]thiazolidin-2-ylidene}cyanamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8850(12)
_cell_length_b                   7.5965(15)
_cell_length_c                   28.273(6)
_cell_measurement_reflns_used    193
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.876
_cell_measurement_theta_min      1.440
_cell_volume                     1264.0(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9219
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_correction_T_min  0.9400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Crystalclear; Rigaku, 2005)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.341
_refine_ls_abs_structure_details 'Flack (1983), 6200 Friedel pairs'
_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     155
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0534P)²+0.0295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                2640
_reflns_number_total             3019
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5002.cif
_cod_data_source_block           I
_cod_database_code               2227021
_cod_database_fobs_code          2227021
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Cl Cl1 0.31420(16) -0.62970(7) 0.98241(2) 0.0438(2) Uani d . 1 . .
S S1 0.18444(12) 0.16944(8) 0.77090(2) 0.03081(17) Uani d . 1 . .
N N2 0.2773(4) 0.3380(3) 0.85392(7) 0.0279(4) Uani d . 1 . .
C C9 0.3024(4) 0.1982(3) 0.82718(8) 0.0238(5) Uani d . 1 . .
C C1 0.2990(4) -0.1331(3) 0.93777(8) 0.0267(5) Uani d . 1 . .
H H1 0.2024 -0.0368 0.9407 0.032 Uiso calc R 1 . .
N N1 0.4250(4) 0.0594(2) 0.84129(6) 0.0255(5) Uani d . 1 . .
C C6 0.4992(4) -0.1158(3) 0.91192(8) 0.0242(5) Uani d . 1 . .
C C7 0.5466(4) 0.0572(3) 0.88698(8) 0.0257(5) Uani d . 1 . .
H H7 0.4806 0.1507 0.9065 0.031 Uiso calc R 1 . .
C C8 0.7950(5) 0.1029(4) 0.87970(9) 0.0369(6) Uani d . 1 . .
H H8A 0.8064 0.2125 0.8630 0.055 Uiso calc R 1 . .
H H8B 0.8672 0.0117 0.8616 0.055 Uiso calc R 1 . .
H H8C 0.8686 0.1135 0.9099 0.055 Uiso calc R 1 . .
C C12 0.1462(5) 0.4672(3) 0.83801(8) 0.0294(6) Uani d . 1 . .
C C2 0.2409(4) -0.2905(3) 0.95914(8) 0.0288(5) Uani d . 1 . .
H H2 0.1055 -0.3011 0.9759 0.035 Uiso calc R 1 . .
C C4 0.5886(5) -0.4192(3) 0.93042(9) 0.0316(6) Uani d . 1 . .
H H4 0.6860 -0.5152 0.9284 0.038 Uiso calc R 1 . .
C C3 0.3874(5) -0.4315(3) 0.95515(8) 0.0285(5) Uani d . 1 . .
N N3 0.0347(5) 0.5868(3) 0.82737(8) 0.0414(6) Uani d . 1 . .
C C5 0.6432(5) -0.2610(3) 0.90865(8) 0.0292(6) Uani d . 1 . .
H H5 0.7778 -0.2518 0.8916 0.035 Uiso calc R 1 . .
C C11 0.4588(7) -0.0759(4) 0.80600(9) 0.0479(8) Uani d . 1 . .
H H11A 0.6166 -0.0769 0.7961 0.058 Uiso calc R 1 . .
H H11B 0.4235 -0.1901 0.8195 0.058 Uiso calc R 1 . .
C C10 0.3144(8) -0.0437(4) 0.76555(12) 0.0648(12) Uani d . 1 . .
H H10A 0.1977 -0.1336 0.7638 0.078 Uiso calc R 1 . .
H H10B 0.4039 -0.0488 0.7368 0.078 Uiso calc R 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C9 S1 C10 . . 91.16(13) ?
C9 N2 C12 . . 118.0(2) ?
N2 C9 N1 . . 121.8(2) ?
N2 C9 S1 . . 125.49(18) ?
N1 C9 S1 . . 112.73(17) ?
C2 C1 C6 . . 121.3(2) ?
C2 C1 H1 . . 119.3 ?
C6 C1 H1 . . 119.3 ?
C9 N1 C11 . . 115.4(2) ?
C9 N1 C7 . . 122.06(19) ?
C11 N1 C7 . . 121.9(2) ?
C1 C6 C5 . . 118.3(2) ?
C1 C6 C7 . . 118.8(2) ?
C5 C6 C7 . . 122.9(2) ?
N1 C7 C8 . . 110.2(2) ?
N1 C7 C6 . . 109.10(19) ?
C8 C7 C6 . . 116.0(2) ?
N1 C7 H7 . . 107.0 ?
C8 C7 H7 . . 107.0 ?
C6 C7 H7 . . 107.0 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N3 C12 N2 . . 174.7(3) ?
C3 C2 C1 . . 118.8(2) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
C3 C4 C5 . . 118.9(2) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C4 C3 C2 . . 121.7(2) ?
C4 C3 Cl1 . . 119.64(19) ?
C2 C3 Cl1 . . 118.6(2) ?
C4 C5 C6 . . 121.0(2) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C10 C11 N1 . . 110.1(2) ?
C10 C11 H11A . . 109.6 ?
N1 C11 H11A . . 109.6 ?
C10 C11 H11B . . 109.6 ?
N1 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.1 ?
C11 C10 S1 . . 109.6(2) ?
C11 C10 H10A . . 109.7 ?
S1 C10 H10A . . 109.7 ?
C11 C10 H10B . . 109.7 ?
S1 C10 H10B . . 109.7 ?
H10A C10 H10B . . 108.2 ?
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
Cl1 C3 . 1.746(2) ?
S1 C9 . 1.750(2) ?
S1 C10 . 1.797(3) ?
N2 C9 . 1.311(3) ?
N2 C12 . 1.327(3) ?
C9 N1 . 1.338(3) ?
C1 C2 . 1.383(3) ?
C1 C6 . 1.393(3) ?
C1 H1 . 0.9300 ?
N1 C11 . 1.446(3) ?
N1 C7 . 1.477(3) ?
C6 C5 . 1.394(3) ?
C6 C7 . 1.517(3) ?
C7 C8 . 1.516(4) ?
C7 H7 . 0.9800 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C12 N3 . 1.161(3) ?
C2 C3 . 1.380(4) ?
C2 H2 . 0.9300 ?
C4 C3 . 1.378(4) ?
C4 C5 . 1.388(3) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C11 C10 . 1.446(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 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
C10 H10A S1 3_546 0.97 2.87 3.799(4) 159.8
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
C12 N2 C9 N1 . . . . -177.6(2) ?
C12 N2 C9 S1 . . . . 2.1(3) ?
C10 S1 C9 N2 . . . . 179.1(3) ?
C10 S1 C9 N1 . . . . -1.1(2) ?
N2 C9 N1 C11 . . . . -173.2(2) ?
S1 C9 N1 C11 . . . . 7.0(3) ?
N2 C9 N1 C7 . . . . -2.4(4) ?
S1 C9 N1 C7 . . . . 177.89(18) ?
C2 C1 C6 C5 . . . . -1.1(4) ?
C2 C1 C6 C7 . . . . 176.5(2) ?
C9 N1 C7 C8 . . . . -98.3(3) ?
C11 N1 C7 C8 . . . . 72.0(3) ?
C9 N1 C7 C6 . . . . 133.2(2) ?
C11 N1 C7 C6 . . . . -56.5(3) ?
C1 C6 C7 N1 . . . . -82.5(3) ?
C5 C6 C7 N1 . . . . 94.9(3) ?
C1 C6 C7 C8 . . . . 152.3(2) ?
C5 C6 C7 C8 . . . . -30.3(3) ?
C9 N2 C12 N3 . . . . 18E1(10) ?
C6 C1 C2 C3 . . . . 1.1(4) ?
C5 C4 C3 C2 . . . . -0.6(4) ?
C5 C4 C3 Cl1 . . . . 179.5(2) ?
C1 C2 C3 C4 . . . . -0.2(4) ?
C1 C2 C3 Cl1 . . . . 179.7(2) ?
C3 C4 C5 C6 . . . . 0.6(4) ?
C1 C6 C5 C4 . . . . 0.2(4) ?
C7 C6 C5 C4 . . . . -177.3(2) ?
C9 N1 C11 C10 . . . . -10.7(4) ?
C7 N1 C11 C10 . . . . 178.5(3) ?
N1 C11 C10 S1 . . . . 9.2(4) ?
C9 S1 C10 C11 . . . . -4.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745673
