#------------------------------------------------------------------------------
#$Date: 2017-05-05 00:48:06 +0300 (Fri, 05 May 2017) $
#$Revision: 196141 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/24/4032428.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_4032428
loop_
_publ_author_name
'Filimonov, Valeriy O.'
'Dianova, Lidia N.'
'Galata, Kristina A.'
'Beryozkina, Tetyana V.'
'Novikov, Mikhail S.'
'Berseneva, Vera S.'
'Eltsov, Oleg S.'
'Lebedev, Albert T.'
'Slepukhin, Pavel A.'
'Bakulev, Vasiliy A.'
_publ_section_title
;
 Switchable Synthesis of 4,5-Functionalized 1,2,3-Thiadiazoles and
 1,2,3-Triazoles from 2-Cyanothioacetamides under Diazo Group Transfer
 Conditions.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4056
_journal_page_last               4071
_journal_paper_doi               10.1021/acs.joc.6b02736
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C15 H19 N5 O2 S2'
_chemical_formula_sum            'C15 H19 N5 O2 S2'
_chemical_formula_weight         365.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 101.401(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0324(9)
_cell_length_b                   17.4049(12)
_cell_length_c                   10.1453(6)
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.86
_cell_volume                     1736.5(2)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Xcalibur S CCD'
_diffrn_measurement_method       'omega scans'
_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8136
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0389
_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)+(0.0420P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                2182
_reflns_number_total             4053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02736_si_001.cif
_cod_data_source_block           dc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032428--4032429.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4032428
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_refinement_flags
S1 S 0.04989(5) 0.13616(3) 0.68911(5) 0.04986(16) Uani 1 1 d .
N1 N 0.49453(18) 0.05025(9) 0.61677(18) 0.0636(5) Uani 1 1 d .
O1 O 0.04224(16) 0.11989(8) 0.82510(14) 0.0698(4) Uani 1 1 d .
C1 C -0.1542(3) 0.45838(14) 0.5641(3) 0.1079(10) Uani 1 1 d .
H1A H -0.1903 0.4620 0.4694 0.162 Uiso 1 1 calc R
H1B H -0.0818 0.4949 0.5887 0.162 Uiso 1 1 calc R
H1C H -0.2247 0.4692 0.6130 0.162 Uiso 1 1 calc R
C2 C 0.27235(18) 0.09866(9) 0.61338(17) 0.0403(4) Uani 1 1 d .
O2 O -0.02459(14) 0.08640(7) 0.58698(15) 0.0676(4) Uani 1 1 d .
N2 N 0.62345(19) 0.06070(10) 0.6348(2) 0.0784(6) Uani 1 1 d .
S3 S 0.66132(6) 0.15452(3) 0.65592(6) 0.06872(19) Uani 1 1 d .
N3 N 0.45979(16) 0.25580(8) 0.64949(17) 0.0553(4) Uani 1 1 d .
C3 C 0.0038(2) 0.28383(11) 0.75459(18) 0.0543(5) Uani 1 1 d .
H3A H 0.0433 0.2704 0.8424 0.065 Uiso 1 1 calc R
N4 N 0.20765(15) 0.14475(8) 0.68076(15) 0.0476(4) Uani 1 1 d .
C4 C 0.49422(19) 0.18141(10) 0.64269(18) 0.0464(4) Uani 1 1 d .
N5 N 0.2241(2) 0.03817(10) 0.5435(2) 0.0656(5) Uani 1 1 d .
H5A H 0.143(2) 0.0282(11) 0.5395(19) 0.062(7) Uiso 1 1 d .
H5B H 0.273(3) 0.0131(12) 0.496(2) 0.083(8) Uiso 1 1 d .
C5 C 0.41746(18) 0.11367(9) 0.62113(17) 0.0439(4) Uani 1 1 d .
C6 C 0.3374(2) 0.28499(10) 0.5597(2) 0.0626(6) Uani 1 1 d .
H6A H 0.2653 0.2472 0.5528 0.075 Uiso 1 1 calc R
H6B H 0.3565 0.2927 0.4706 0.075 Uiso 1 1 calc R
C7 C 0.2910(3) 0.35874(11) 0.6095(3) 0.0850(8) Uani 1 1 d .
H7A H 0.2619 0.3500 0.6939 0.102 Uiso 1 1 calc R
H7B H 0.2138 0.3782 0.5451 0.102 Uiso 1 1 calc R
C8 C 0.4043(3) 0.41785(12) 0.6301(3) 0.0884(8) Uani 1 1 d .
H8A H 0.4275 0.4306 0.5443 0.106 Uiso 1 1 calc R
H8B H 0.3741 0.4644 0.6678 0.106 Uiso 1 1 calc R
C9 C 0.5265(3) 0.38658(12) 0.7231(3) 0.0838(8) Uani 1 1 d .
H9A H 0.6003 0.4234 0.7311 0.101 Uiso 1 1 calc R
H9B H 0.5055 0.3794 0.8116 0.101 Uiso 1 1 calc R
C10 C 0.5710(2) 0.31199(12) 0.6742(3) 0.0758(7) Uani 1 1 d .
H10A H 0.6038 0.3205 0.5917 0.091 Uiso 1 1 calc R
H10B H 0.6456 0.2915 0.7406 0.091 Uiso 1 1 calc R
C11 C -0.00833(18) 0.23004(10) 0.65380(18) 0.0442(4) Uani 1 1 d .
C12 C -0.0665(2) 0.25091(13) 0.5242(2) 0.0599(5) Uani 1 1 d .
H12A H -0.0751 0.2152 0.4548 0.072 Uiso 1 1 calc R
C13 C -0.1114(2) 0.32429(14) 0.4985(2) 0.0720(6) Uani 1 1 d .
H13A H -0.1508 0.3379 0.4108 0.086 Uiso 1 1 calc R
C14 C -0.1003(2) 0.37857(12) 0.5974(3) 0.0656(6) Uani 1 1 d .
C15 C -0.0421(2) 0.35707(11) 0.7258(2) 0.0654(6) Uani 1 1 d .
H15A H -0.0337 0.3930 0.7948 0.078 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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'
N N 0.0061 0.0033 '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
O1 S1 O2 117.21(9)
O1 S1 N4 108.14(9)
O2 S1 N4 113.19(8)
O1 S1 C11 107.72(8)
O2 S1 C11 108.03(9)
N4 S1 C11 101.22(8)
N2 N1 C5 116.49(16)
C14 C1 H1A 109.5
C14 C1 H1B 109.5
H1A C1 H1B 109.5
C14 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N4 C2 N5 127.51(18)
N4 C2 C5 116.96(15)
N5 C2 C5 115.46(16)
N1 N2 S3 110.61(13)
N2 S3 C4 93.57(9)
C4 N3 C10 117.14(17)
C4 N3 C6 119.55(16)
C10 N3 C6 112.96(16)
C15 C3 C11 119.98(19)
C15 C3 H3A 120.0
C11 C3 H3A 120.0
C2 N4 S1 124.49(13)
N3 C4 C5 132.76(18)
N3 C4 S3 120.93(14)
C5 C4 S3 106.27(13)
C2 N5 H5A 116.8(13)
C2 N5 H5B 120.9(16)
H5A N5 H5B 122(2)
N1 C5 C4 113.04(17)
N1 C5 C2 114.87(15)
C4 C5 C2 131.87(16)
N3 C6 C7 111.56(19)
N3 C6 H6A 109.3
C7 C6 H6A 109.3
N3 C6 H6B 109.3
C7 C6 H6B 109.3
H6A C6 H6B 108.0
C6 C7 C8 110.9(2)
C6 C7 H7A 109.5
C8 C7 H7A 109.5
C6 C7 H7B 109.5
C8 C7 H7B 109.5
H7A C7 H7B 108.1
C9 C8 C7 109.8(2)
C9 C8 H8A 109.7
C7 C8 H8A 109.7
C9 C8 H8B 109.7
C7 C8 H8B 109.7
H8A C8 H8B 108.2
C10 C9 C8 111.7(2)
C10 C9 H9A 109.3
C8 C9 H9A 109.3
C10 C9 H9B 109.3
C8 C9 H9B 109.3
H9A C9 H9B 107.9
N3 C10 C9 111.7(2)
N3 C10 H10A 109.3
C9 C10 H10A 109.3
N3 C10 H10B 109.3
C9 C10 H10B 109.3
H10A C10 H10B 107.9
C3 C11 C12 119.30(17)
C3 C11 S1 120.49(14)
C12 C11 S1 120.21(14)
C13 C12 C11 119.44(19)
C13 C12 H12A 120.3
C11 C12 H12A 120.3
C12 C13 C14 122.1(2)
C12 C13 H13A 118.9
C14 C13 H13A 118.9
C13 C14 C15 117.83(19)
C13 C14 C1 120.0(2)
C15 C14 C1 122.1(2)
C3 C15 C14 121.3(2)
C3 C15 H15A 119.3
C14 C15 H15A 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4252(14)
S1 O2 1.4408(14)
S1 N4 1.6085(15)
S1 C11 1.7484(18)
N1 N2 1.283(2)
N1 C5 1.353(2)
C1 C14 1.504(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 N4 1.307(2)
C2 N5 1.308(2)
C2 C5 1.466(2)
N2 S3 1.6807(18)
S3 C4 1.7201(19)
N3 C4 1.345(2)
N3 C10 1.467(2)
N3 C6 1.468(3)
C3 C15 1.367(3)
C3 C11 1.374(2)
C3 H3A 0.9300
C4 C5 1.402(2)
N5 H5A 0.83(2)
N5 H5B 0.87(2)
C6 C7 1.487(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.516(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.494(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.489(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.378(3)
C12 C13 1.362(3)
C12 H12A 0.9300
C13 C14 1.367(3)
C13 H13A 0.9300
C14 C15 1.370(3)
C15 H15A 0.9300
