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#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/55/1545523.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_1545523
loop_
_publ_author_name
'Sonia, A. S.'
'Baskaran, R.'
'Selvanayagam, S.'
_publ_section_title
;
 Crystal structure of
 3-[({[bis(2-cyanoethyl)carbamothioyl]disulfanyl}methanethioyl)(2-cyanoethyl)
 amino]propanenitrile
;
_journal_coeditor_code           LH4017
_journal_issue                   3
_journal_name_full               IUCrData
_journal_page_first              x170346
_journal_paper_doi               10.1107/S2414314617003467
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C14 H16 N6 S4'
_chemical_formula_moiety         'C14 H16 N6 S4'
_chemical_formula_sum            'C14 H16 N6 S4'
_chemical_formula_weight         396.57
_chemical_name_systematic
3-[({[bis(2-Cyanoethyl)carbamothioyl]disulfanyl}methanethioyl)(2-cyanoethyl)amino]propanenitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 108.713(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4313(7)
_cell_length_b                   5.6117(2)
_cell_length_c                   22.8702(12)
_cell_measurement_reflns_used    8307
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.7
_cell_measurement_theta_min      2.3
_cell_volume                     1875.77(15)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.975
_diffrn_reflns_theta_min         2.787
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         3347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²+1.4682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                2569
_reflns_number_total             3347
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh4017sup1.cif
_cod_data_source_block           I
_cod_database_code               1545523
_cod_database_fobs_code          1545523
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.861
_shelx_estimated_absorpt_t_max   0.904
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_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_occupancy
S S1 -0.00264(3) 0.57876(7) 0.20581(2) 0.03874(11) Uani d 1
S S2 0.13996(3) 0.20336(9) 0.26542(2) 0.05086(14) Uani d 1
N N1 0.06850(8) 0.2800(2) 0.14508(5) 0.0328(2) Uani d 1
N N2 -0.09703(13) -0.1278(3) 0.02598(9) 0.0644(5) Uani d 1
N N3 0.21226(12) 0.6016(3) 0.08156(8) 0.0610(4) Uani d 1
C C1 0.07351(10) 0.3344(3) 0.20300(6) 0.0325(3) Uani d 1
C C2 0.00524(10) 0.3986(3) 0.09077(6) 0.0351(3) Uani d 1
H H2A 0.0289 0.3838 0.0565 0.042 Uiso calc 1
H H2B 0.0027 0.5669 0.0997 0.042 Uiso calc 1
C C3 -0.09148(10) 0.2961(3) 0.07169(7) 0.0388(3) Uani d 1
H H3A -0.1125 0.2922 0.1074 0.047 Uiso calc 1
H H3B -0.1322 0.3997 0.0411 0.047 Uiso calc 1
C C4 -0.09592(11) 0.0566(3) 0.04630(8) 0.0429(3) Uani d 1
C C5 0.12945(11) 0.0991(3) 0.13344(8) 0.0389(3) Uani d 1
H H5A 0.1026 0.0367 0.0920 0.047 Uiso calc 1
H H5B 0.1356 -0.0318 0.1622 0.047 Uiso calc 1
C C6 0.22415(11) 0.2006(3) 0.14036(9) 0.0487(4) Uani d 1
H H6A 0.2567 0.2279 0.1838 0.058 Uiso calc 1
H H6B 0.2586 0.0851 0.1252 0.058 Uiso calc 1
C C7 0.21877(11) 0.4242(4) 0.10651(8) 0.0455(4) Uani 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'
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_3
_geom_angle
C1 S1 S1 2 102.62(5)
C1 N1 C5 . 120.13(12)
C1 N1 C2 . 123.03(12)
C5 N1 C2 . 116.82(12)
N1 C1 S2 . 125.50(11)
N1 C1 S1 . 111.98(10)
S2 C1 S1 . 122.52(8)
N1 C2 C3 . 113.23(12)
N1 C2 H2A . 108.9
C3 C2 H2A . 108.9
N1 C2 H2B . 108.9
C3 C2 H2B . 108.9
H2A C2 H2B . 107.7
C4 C3 C2 . 112.20(14)
C4 C3 H3A . 109.2
C2 C3 H3A . 109.2
C4 C3 H3B . 109.2
C2 C3 H3B . 109.2
H3A C3 H3B . 107.9
N2 C4 C3 . 177.8(2)
N1 C5 C6 . 111.78(13)
N1 C5 H5A . 109.3
C6 C5 H5A . 109.3
N1 C5 H5B . 109.3
C6 C5 H5B . 109.3
H5A C5 H5B . 107.9
C7 C6 C5 . 112.02(14)
C7 C6 H6A . 109.2
C5 C6 H6A . 109.2
C7 C6 H6B . 109.2
C5 C6 H6B . 109.2
H6A C6 H6B . 107.9
N3 C7 C6 . 177.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C1 . 1.8201(15)
S1 S1 2 1.9968(7)
S2 C1 . 1.6405(14)
N1 C1 . 1.3375(18)
N1 C5 . 1.4651(19)
N1 C2 . 1.4699(18)
N2 C4 . 1.132(2)
N3 C7 . 1.136(3)
C2 C3 . 1.527(2)
C2 H2A . 0.9700
C2 H2B . 0.9700
C3 C4 . 1.457(2)
C3 H3A . 0.9700
C3 H3B . 0.9700
C5 C6 . 1.529(2)
C5 H5A . 0.9700
C5 H5B . 0.9700
C6 C7 . 1.462(3)
C6 H6A . 0.9700
C6 H6B . 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
C2 H2B S1 . 0.97 2.46 2.857(2) 105
C3 H3A S1 . 0.97 2.84 3.332(2) 112
C5 H5B S2 . 0.97 2.69 3.028(2) 101
C2 H2B N2 1_565 0.97 2.55 3.202(2) 125
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
C5 N1 C1 S2 . -3.8(2)
C2 N1 C1 S2 . 177.86(11)
C5 N1 C1 S1 . 175.66(10)
C2 N1 C1 S1 . -2.67(17)
S1 S1 C1 N1 2 170.16(9)
S1 S1 C1 S2 2 -10.36(10)
C1 N1 C2 C3 . -82.14(17)
C5 N1 C2 C3 . 99.48(15)
N1 C2 C3 C4 . -69.60(17)
C1 N1 C5 C6 . -81.15(18)
C2 N1 C5 C6 . 97.28(16)
N1 C5 C6 C7 . -48.7(2)
