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#$Date: 2021-08-24 04:18:37 +0300 (Tue, 24 Aug 2021) $
#$Revision: 268180 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/34/7243415.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_7243415
loop_
_publ_author_name
'Vinogradova, Ekaterina E.'
'Gazieva, Galina A.'
'Izmest'ev, Alexei N.'
'Karnoukhova, Valentina A.'
'Kravchenko, Angelina N.'
_publ_section_title
;
 Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis
 of 2-hydrazonoimidazo[4,5-d]thiazolones
;
_journal_issue                   45
_journal_name_full               'RSC Advances'
_journal_page_first              28395
_journal_page_last               28400
_journal_paper_doi               10.1039/D1RA05568B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C13 H15 N5 O S'
_chemical_formula_sum            'C13 H15 N5 O S'
_chemical_formula_weight         289.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-08-09 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7481(5)
_cell_length_b                   9.6628(4)
_cell_length_c                   30.3545(14)
_cell_measurement_reflns_used    229
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     2859.2(2)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            41443
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         2.483
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0418
_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)+(0.0447P)²+2.3493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2120
_reflns_number_total             2955
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d1ra05568b2.cif
_cod_data_source_block           10a
_cod_database_code               7243415
_shelx_shelxl_version_number     2016/6
_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   0.941
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51179(6) 0.70511(6) 0.37183(2) 0.02442(16) Uani 1 1 d . . . . .
O1 O 0.70048(16) 0.92656(17) 0.49071(5) 0.0281(4) Uani 1 1 d . . . . .
N1 N 0.58344(18) 0.9298(2) 0.42465(6) 0.0233(4) Uani 1 1 d . . . . .
N2 N 0.50006(18) 0.8024(2) 0.47921(6) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.33500(19) 0.6723(2) 0.43525(7) 0.0233(4) Uani 1 1 d . . . . .
H3 H 0.287(3) 0.627(3) 0.4549(9) 0.040(8) Uiso 1 1 d . . . . .
N4 N 0.36954(18) 0.4720(2) 0.39573(6) 0.0246(4) Uani 1 1 d . . . . .
N5 N 0.44875(19) 0.4157(2) 0.36139(6) 0.0250(5) Uani 1 1 d . . . . .
C1 C 0.6039(2) 0.8880(2) 0.46739(8) 0.0232(5) Uani 1 1 d . . . . .
C2 C 0.3906(2) 0.8051(2) 0.44616(7) 0.0216(5) Uani 1 1 d . . . . .
H2A H 0.316145 0.870428 0.455157 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3990(2) 0.6004(2) 0.40292(7) 0.0218(5) Uani 1 1 d . . . . .
C4 C 0.4674(2) 0.8604(2) 0.40559(7) 0.0221(5) Uani 1 1 d . . . . .
H4A H 0.408934 0.926337 0.388506 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4125(2) 0.2917(2) 0.35210(7) 0.0249(5) Uani 1 1 d . . . . .
H5A H 0.334527 0.253675 0.366463 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4866(2) 0.2064(2) 0.32021(7) 0.0234(5) Uani 1 1 d . . . . .
C7 C 0.4340(2) 0.0766(3) 0.30939(8) 0.0271(5) Uani 1 1 d . . . . .
H7A H 0.348770 0.047868 0.321524 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5043(3) -0.0111(3) 0.28114(8) 0.0313(6) Uani 1 1 d . . . . .
H8A H 0.467169 -0.099044 0.273852 0.038 Uiso 1 1 calc R U . . .
C9 C 0.6289(3) 0.0303(3) 0.26360(8) 0.0353(6) Uani 1 1 d . . . . .
H9A H 0.677641 -0.029489 0.244286 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6825(3) 0.1587(3) 0.27424(8) 0.0335(6) Uani 1 1 d . . . . .
H10A H 0.768147 0.186479 0.262188 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6125(2) 0.2471(3) 0.30230(8) 0.0276(5) Uani 1 1 d . . . . .
H11A H 0.649867 0.335142 0.309339 0.033 Uiso 1 1 calc R U . . .
C12 C 0.6949(2) 0.9860(3) 0.39826(8) 0.0332(6) Uani 1 1 d . . . . .
H12A H 0.760799 1.032830 0.417526 0.050 Uiso 1 1 calc R U . . .
H12B H 0.657865 1.052339 0.376927 0.050 Uiso 1 1 calc R U . . .
H12C H 0.740958 0.910591 0.382529 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4764(3) 0.7553(3) 0.52395(8) 0.0310(6) Uani 1 1 d . . . . .
H13A H 0.556612 0.777188 0.542142 0.046 Uiso 1 1 calc R U . . .
H13B H 0.461324 0.655052 0.523934 0.046 Uiso 1 1 calc R U . . .
H13C H 0.395415 0.801924 0.536001 0.046 Uiso 1 1 calc R U . . .
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C4 91.30(10) . . ?
C1 N1 C4 110.93(18) . . ?
C1 N1 C12 121.45(19) . . ?
C4 N1 C12 122.70(19) . . ?
C1 N2 C13 123.89(19) . . ?
C1 N2 C2 110.58(18) . . ?
C13 N2 C2 122.10(18) . . ?
C3 N3 C2 116.96(19) . . ?
C3 N3 H3 118.8(19) . . ?
C2 N3 H3 119.5(18) . . ?
C3 N4 N5 112.02(19) . . ?
C5 N5 N4 111.94(19) . . ?
O1 C1 N2 127.0(2) . . ?
O1 C1 N1 124.3(2) . . ?
N2 C1 N1 108.73(19) . . ?
N3 C2 N2 114.71(19) . . ?
N3 C2 C4 108.07(18) . . ?
N2 C2 C4 101.58(16) . . ?
N3 C2 H2A 110.7 . . ?
N2 C2 H2A 110.7 . . ?
C4 C2 H2A 110.7 . . ?
N4 C3 N3 120.9(2) . . ?
N4 C3 S1 126.70(18) . . ?
N3 C3 S1 112.27(17) . . ?
N1 C4 C2 102.87(18) . . ?
N1 C4 S1 114.42(15) . . ?
C2 C4 S1 105.88(15) . . ?
N1 C4 H4A 111.1 . . ?
C2 C4 H4A 111.1 . . ?
S1 C4 H4A 111.1 . . ?
N5 C5 C6 122.4(2) . . ?
N5 C5 H5A 118.8 . . ?
C6 C5 H5A 118.8 . . ?
C7 C6 C11 119.0(2) . . ?
C7 C6 C5 118.7(2) . . ?
C11 C6 C5 122.2(2) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C10 C11 C6 119.9(2) . . ?
C10 C11 H11A 120.1 . . ?
C6 C11 H11A 120.1 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.768(2) . ?
S1 C4 1.868(2) . ?
O1 C1 1.236(3) . ?
N1 C1 1.373(3) . ?
N1 C4 1.437(3) . ?
N1 C12 1.455(3) . ?
N2 C1 1.356(3) . ?
N2 C13 1.451(3) . ?
N2 C2 1.464(3) . ?
N3 C3 1.355(3) . ?
N3 C2 1.432(3) . ?
N3 H3 0.88(3) . ?
N4 C3 1.291(3) . ?
N4 N5 1.407(3) . ?
N5 C5 1.281(3) . ?
C2 C4 1.536(3) . ?
C2 H2A 1.0000 . ?
C4 H4A 1.0000 . ?
C5 C6 1.462(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.395(3) . ?
C6 C11 1.398(3) . ?
C7 C8 1.387(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.386(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.384(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
N3 H3 O1 0.88(3) 1.92(3) 2.772(3) 162(3) 2_466
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N4 N5 C5 -175.2(2) . . . . ?
C13 N2 C1 O1 8.3(4) . . . . ?
C2 N2 C1 O1 167.6(2) . . . . ?
C13 N2 C1 N1 -170.1(2) . . . . ?
C2 N2 C1 N1 -10.8(3) . . . . ?
C4 N1 C1 O1 176.4(2) . . . . ?
C12 N1 C1 O1 20.7(4) . . . . ?
C4 N1 C1 N2 -5.1(3) . . . . ?
C12 N1 C1 N2 -160.9(2) . . . . ?
C3 N3 C2 N2 -87.3(2) . . . . ?
C3 N3 C2 C4 25.2(3) . . . . ?
C1 N2 C2 N3 137.0(2) . . . . ?
C13 N2 C2 N3 -63.2(3) . . . . ?
C1 N2 C2 C4 20.7(2) . . . . ?
C13 N2 C2 C4 -179.5(2) . . . . ?
N5 N4 C3 N3 -178.96(19) . . . . ?
N5 N4 C3 S1 5.6(3) . . . . ?
C2 N3 C3 N4 169.1(2) . . . . ?
C2 N3 C3 S1 -14.9(2) . . . . ?
C4 S1 C3 N4 175.5(2) . . . . ?
C4 S1 C3 N3 -0.28(17) . . . . ?
C1 N1 C4 C2 17.5(2) . . . . ?
C12 N1 C4 C2 173.0(2) . . . . ?
C1 N1 C4 S1 -96.79(19) . . . . ?
C12 N1 C4 S1 58.6(3) . . . . ?
N3 C2 C4 N1 -143.05(18) . . . . ?
N2 C2 C4 N1 -22.0(2) . . . . ?
N3 C2 C4 S1 -22.7(2) . . . . ?
N2 C2 C4 S1 98.39(16) . . . . ?
C3 S1 C4 N1 125.83(17) . . . . ?
C3 S1 C4 C2 13.28(15) . . . . ?
N4 N5 C5 C6 -174.63(19) . . . . ?
N5 C5 C6 C7 -174.9(2) . . . . ?
N5 C5 C6 C11 9.0(3) . . . . ?
C11 C6 C7 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 -176.5(2) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C6 0.2(4) . . . . ?
C7 C6 C11 C10 0.0(3) . . . . ?
C5 C6 C11 C10 176.1(2) . . . . ?
