#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:40:38 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270494 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158333.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_7158333
loop_
_publ_author_name
'Kutasevich, Anton V.'
'Niktarov, Anton S.'
'Uvarova, Ekaterina S.'
'Karnoukhova, Valentina A.'
'Mityanov, Vitaly S.'
_publ_section_title
;
 A novel approach to bis(1,3-azol-2-yl)acetonitriles and
 bis(1,3-azol-2-yl)methanes via the [3 + 2]-dipolar cycloaddition
 of imidazole N-oxides and 2-heteroaryl-3,3-dimethylacrylonitriles.
;
_journal_issue                   41
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8988
_journal_page_last               8998
_journal_paper_doi               10.1039/d1ob01441b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C15 H14 N4 S'
_chemical_formula_sum            'C15 H14 N4 S'
_chemical_formula_weight         282.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-06-30 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.235(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3093(4)
_cell_length_b                   7.7536(3)
_cell_length_c                   21.1019(9)
_cell_measurement_reflns_used    246
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1355.82(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_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      120(2)
_diffrn_detector_type            'Bruker PHOTON II CPAD detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17592
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.523
_diffrn_reflns_theta_min         1.935
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0341
_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)+(0.0565P)²+0.4125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3525
_reflns_number_total             4117
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d1ob01441b2.cif
_cod_data_source_block           mvs663dmf
_cod_depositor_comments
'Adding full bibliography for 7158333--7158334.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158333
_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   0.933
_shelx_estimated_absorpt_t_max   0.961
loop_
_space_group_symop_operation_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_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 0.30464(3) 0.57028(4) 0.31952(2) 0.01901(9) Uani 1 1 d . . . . .
N1 N 0.57228(11) 0.57778(12) 0.39250(4) 0.01641(18) Uani 1 1 d . . . . .
N2 N 0.03711(13) 0.74469(18) 0.42895(6) 0.0340(3) Uani 1 1 d . . . . .
N3 N 0.40245(10) 0.83634(12) 0.55092(4) 0.01542(18) Uani 1 1 d . . . . .
N4 N 0.60230(11) 0.72411(12) 0.50518(4) 0.01595(18) Uani 1 1 d . . . . .
H4N H 0.6456(19) 0.668(2) 0.4769(8) 0.030(4) Uiso 1 1 d . . . . .
C1 C 0.41799(13) 0.61920(14) 0.39168(5) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.47857(14) 0.48759(14) 0.28963(5) 0.0177(2) Uani 1 1 d . . . . .
C3 C 0.49860(15) 0.41541(14) 0.23011(5) 0.0212(2) Uani 1 1 d . . . . .
H3A H 0.410593 0.407726 0.198838 0.025 Uiso 1 1 calc R U . . .
C4 C 0.65050(16) 0.35519(15) 0.21785(6) 0.0233(2) Uani 1 1 d . . . . .
H4A H 0.666642 0.305044 0.177732 0.028 Uiso 1 1 calc R U . . .
C5 C 0.78008(15) 0.36745(15) 0.26384(6) 0.0229(2) Uani 1 1 d . . . . .
H5A H 0.882810 0.324278 0.254677 0.027 Uiso 1 1 calc R U . . .
C6 C 0.76099(14) 0.44165(14) 0.32265(5) 0.0197(2) Uani 1 1 d . . . . .
H6A H 0.849981 0.450991 0.353413 0.024 Uiso 1 1 calc R U . . .
C7 C 0.60868(13) 0.50244(14) 0.33589(5) 0.0168(2) Uani 1 1 d . . . . .
C8 C 0.34418(12) 0.70086(14) 0.44262(5) 0.0165(2) Uani 1 1 d . . . . .
C9 C 0.17504(14) 0.72716(16) 0.43627(5) 0.0213(2) Uani 1 1 d . . . . .
C10 C 0.44204(12) 0.75267(14) 0.49794(5) 0.0151(2) Uani 1 1 d . . . . .
C11 C 0.54145(12) 0.85720(14) 0.59228(5) 0.0159(2) Uani 1 1 d . . . . .
C12 C 0.66527(13) 0.78766(14) 0.56320(5) 0.0166(2) Uani 1 1 d . . . . .
C13 C 0.24278(14) 0.89662(18) 0.56493(6) 0.0244(2) Uani 1 1 d . . . . .
H13A H 0.165792 0.800929 0.560139 0.037 Uiso 1 1 calc R U . . .
H13B H 0.208445 0.989451 0.535444 0.037 Uiso 1 1 calc R U . . .
H13C H 0.246731 0.940017 0.608638 0.037 Uiso 1 1 calc R U . . .
C14 C 0.53632(14) 0.94212(15) 0.65524(5) 0.0206(2) Uani 1 1 d . . . . .
H14A H 0.643785 0.938222 0.677699 0.031 Uiso 1 1 calc R U . . .
H14B H 0.459176 0.881626 0.680296 0.031 Uiso 1 1 calc R U . . .
H14C H 0.502604 1.062494 0.649248 0.031 Uiso 1 1 calc R U . . .
C15 C 0.84126(13) 0.77492(16) 0.58242(6) 0.0226(2) Uani 1 1 d . . . . .
H15A H 0.859598 0.797912 0.628053 0.034 Uiso 1 1 calc R U . . .
H15B H 0.900206 0.859773 0.558661 0.034 Uiso 1 1 calc R U . . .
H15C H 0.879605 0.658724 0.573189 0.034 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'
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
C2 S1 C1 89.28(5) . . ?
C1 N1 C7 111.43(9) . . ?
C10 N3 C11 109.23(8) . . ?
C10 N3 C13 126.98(9) . . ?
C11 N3 C13 123.78(9) . . ?
C10 N4 C12 110.32(9) . . ?
C10 N4 H4N 118.4(11) . . ?
C12 N4 H4N 131.1(11) . . ?
N1 C1 C8 124.73(10) . . ?
N1 C1 S1 114.41(8) . . ?
C8 C1 S1 120.84(8) . . ?
C3 C2 C7 121.36(11) . . ?
C3 C2 S1 129.10(9) . . ?
C7 C2 S1 109.53(8) . . ?
C4 C3 C2 118.23(11) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C3 C4 C5 120.79(11) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 121.06(11) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C7 118.92(11) . . ?
C5 C6 H6A 120.5 . . ?
C7 C6 H6A 120.5 . . ?
N1 C7 C6 125.03(10) . . ?
N1 C7 C2 115.34(10) . . ?
C6 C7 C2 119.63(10) . . ?
C9 C8 C1 118.15(10) . . ?
C9 C8 C10 122.49(10) . . ?
C1 C8 C10 119.35(9) . . ?
N2 C9 C8 177.30(13) . . ?
N4 C10 N3 106.47(9) . . ?
N4 C10 C8 122.96(10) . . ?
N3 C10 C8 130.57(9) . . ?
C12 C11 N3 106.92(9) . . ?
C12 C11 C14 131.08(10) . . ?
N3 C11 C14 122.00(9) . . ?
C11 C12 N4 107.05(9) . . ?
C11 C12 C15 131.92(10) . . ?
N4 C12 C15 121.02(10) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C2 1.7413(12) . ?
S1 C1 1.7714(11) . ?
N1 C1 1.3205(14) . ?
N1 C7 1.3831(14) . ?
N2 C9 1.1532(15) . ?
N3 C10 1.3539(13) . ?
N3 C11 1.4047(13) . ?
N3 C13 1.4574(14) . ?
N4 C10 1.3474(13) . ?
N4 C12 1.3858(14) . ?
N4 H4N 0.839(17) . ?
C1 C8 1.4249(15) . ?
C2 C3 1.3961(15) . ?
C2 C7 1.4069(15) . ?
C3 C4 1.3880(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3986(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3875(16) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3979(16) . ?
C6 H6A 0.9500 . ?
C8 C9 1.4167(15) . ?
C8 C10 1.4301(14) . ?
C11 C12 1.3487(15) . ?
C11 C14 1.4863(15) . ?
C12 C15 1.4918(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
N4 H4N N1 0.839(17) 1.969(17) 2.6298(13) 135.0(15) .
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
C7 N1 C1 C8 -179.11(10) . . . . ?
C7 N1 C1 S1 -0.81(12) . . . . ?
C2 S1 C1 N1 0.42(9) . . . . ?
C2 S1 C1 C8 178.80(9) . . . . ?
C1 S1 C2 C3 -179.91(11) . . . . ?
C1 S1 C2 C7 0.08(8) . . . . ?
C7 C2 C3 C4 1.15(17) . . . . ?
S1 C2 C3 C4 -178.86(9) . . . . ?
C2 C3 C4 C5 -0.33(17) . . . . ?
C3 C4 C5 C6 -0.70(18) . . . . ?
C4 C5 C6 C7 0.91(17) . . . . ?
C1 N1 C7 C6 -178.71(10) . . . . ?
C1 N1 C7 C2 0.89(13) . . . . ?
C5 C6 C7 N1 179.49(10) . . . . ?
C5 C6 C7 C2 -0.10(16) . . . . ?
C3 C2 C7 N1 179.43(10) . . . . ?
S1 C2 C7 N1 -0.56(12) . . . . ?
C3 C2 C7 C6 -0.95(16) . . . . ?
S1 C2 C7 C6 179.06(8) . . . . ?
N1 C1 C8 C9 -176.00(11) . . . . ?
S1 C1 C8 C9 5.79(14) . . . . ?
N1 C1 C8 C10 3.85(17) . . . . ?
S1 C1 C8 C10 -174.35(8) . . . . ?
C12 N4 C10 N3 0.72(12) . . . . ?
C12 N4 C10 C8 -179.91(10) . . . . ?
C11 N3 C10 N4 -1.02(12) . . . . ?
C13 N3 C10 N4 179.29(10) . . . . ?
C11 N3 C10 C8 179.69(11) . . . . ?
C13 N3 C10 C8 0.00(19) . . . . ?
C9 C8 C10 N4 178.16(11) . . . . ?
C1 C8 C10 N4 -1.68(16) . . . . ?
C9 C8 C10 N3 -2.64(18) . . . . ?
C1 C8 C10 N3 177.51(11) . . . . ?
C10 N3 C11 C12 0.94(12) . . . . ?
C13 N3 C11 C12 -179.35(10) . . . . ?
C10 N3 C11 C14 -178.90(10) . . . . ?
C13 N3 C11 C14 0.80(16) . . . . ?
N3 C11 C12 N4 -0.48(12) . . . . ?
C14 C11 C12 N4 179.35(11) . . . . ?
N3 C11 C12 C15 178.17(11) . . . . ?
C14 C11 C12 C15 -2.0(2) . . . . ?
C10 N4 C12 C11 -0.14(12) . . . . ?
C10 N4 C12 C15 -178.97(10) . . . . ?
