#------------------------------------------------------------------------------
#$Date: 2021-09-17 04:00:47 +0300 (Fri, 17 Sep 2021) $
#$Revision: 269173 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/35/7243532.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_7243532
loop_
_publ_author_name
'Glinyanaya, Nataliya V.'
'Rayenko, Gennady F.'
'Korotkikh, Nikolai I.'
'Rusanov, Eduard B.'
'Ryabitsky, Alexey B.'
'Shvaika, Oles P.'
_publ_section_title
;
 Halogen-containing heteroaromatic carbenes of the 1,2,4-triazole series
 and their transformations
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              30841
_journal_page_last               30848
_journal_paper_doi               10.1039/D1RA04337D
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C21 H31 Br N3 O6.5 S'
_chemical_formula_weight         541.46
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2021-03-10 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.5498(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9632(7)
_cell_length_b                   18.2169(7)
_cell_length_c                   14.9312(5)
_cell_measurement_temperature    173(2)
_cell_volume                     4829.8(3)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28950
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.542
_diffrn_reflns_theta_min         1.601
_exptl_absorpt_coefficient_mu    1.832
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             2248
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.323
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          1.791
_refine_ls_shift/su_mean         0.038
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0975P)²+8.3370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1591
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3819
_reflns_number_total             5022
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra04337d2.cif
_cod_data_source_block           k70
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C21 H31 Br N3 O6.50 S'
_cod_database_code               7243532
_shelx_shelxl_version_number     2016/4
_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   0.506
_shelx_estimated_absorpt_t_max   0.711
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_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
N1 N 0.35820(16) 0.79385(17) 0.3325(2) 0.0314(6) Uani 1 1 d . . . . .
N2 N 0.35871(16) 0.79555(18) 0.2407(2) 0.0345(7) Uani 1 1 d . . . . .
C3 C 0.29538(19) 0.82633(19) 0.1895(2) 0.0300(7) Uani 1 1 d . . . . .
N4 N 0.25405(15) 0.84262(15) 0.24666(18) 0.0252(6) Uani 1 1 d . . . . .
C5 C 0.29540(19) 0.82273(18) 0.3371(2) 0.0269(7) Uani 1 1 d . . . . .
C6 C 0.4241(2) 0.7584(2) 0.4087(3) 0.0380(9) Uani 1 1 d . . . . .
C7A C 0.3933(3) 0.6898(3) 0.4450(4) 0.0556(17) Uani 0.775(7) 1 d . . P A 1
H7A1 H 0.434700 0.665239 0.494833 0.083 Uiso 0.775(7) 1 calc R U P A 1
H7A2 H 0.355061 0.705158 0.471407 0.083 Uiso 0.775(7) 1 calc R U P A 1
H7A3 H 0.370776 0.655920 0.391639 0.083 Uiso 0.775(7) 1 calc R U P A 1
C7B C 0.4151(13) 0.7624(15) 0.5056(13) 0.068(8) Uani 0.225(7) 1 d . . P A 2
H7B1 H 0.415947 0.813813 0.525127 0.102 Uiso 0.225(7) 1 calc R U P A 2
H7B2 H 0.367049 0.740033 0.501483 0.102 Uiso 0.225(7) 1 calc R U P A 2
H7B3 H 0.456546 0.735786 0.552916 0.102 Uiso 0.225(7) 1 calc R U P A 2
C8A C 0.4616(3) 0.8120(4) 0.4882(4) 0.0530(17) Uani 0.775(7) 1 d . . P A 1
H8A1 H 0.504228 0.788065 0.536907 0.080 Uiso 0.775(7) 1 calc R U P A 1
H8A2 H 0.479774 0.854457 0.462126 0.080 Uiso 0.775(7) 1 calc R U P A 1
H8A3 H 0.425248 0.828468 0.517048 0.080 Uiso 0.775(7) 1 calc R U P A 1
C8B C 0.4892(9) 0.8040(11) 0.4032(14) 0.051(6) Uani 0.225(7) 1 d . . P A 2
H8B1 H 0.485957 0.853675 0.426495 0.076 Uiso 0.225(7) 1 calc R U P A 2
H8B2 H 0.536850 0.781361 0.442822 0.076 Uiso 0.225(7) 1 calc R U P A 2
H8B3 H 0.486962 0.806321 0.336675 0.076 Uiso 0.225(7) 1 calc R U P A 2
C9A C 0.4812(3) 0.7314(4) 0.3637(4) 0.064(2) Uani 0.775(7) 1 d . . P A 1
H9A1 H 0.524076 0.708316 0.413081 0.096 Uiso 0.775(7) 1 calc R U P A 1
H9A2 H 0.456872 0.695510 0.313434 0.096 Uiso 0.775(7) 1 calc R U P A 1
H9A3 H 0.498904 0.773156 0.336030 0.096 Uiso 0.775(7) 1 calc R U P A 1
C9B C 0.4233(11) 0.6842(9) 0.3762(15) 0.047(5) Uani 0.225(7) 1 d . . P A 2
H9B1 H 0.379838 0.658317 0.381911 0.071 Uiso 0.225(7) 1 calc R U P A 2
H9B2 H 0.419893 0.684344 0.309158 0.071 Uiso 0.225(7) 1 calc R U P A 2
H9B3 H 0.469781 0.659384 0.415305 0.071 Uiso 0.225(7) 1 calc R U P A 2
C10 C 0.2713(2) 0.83728(18) 0.4206(2) 0.0288(7) Uani 1 1 d . . . . .
H10A H 0.299260 0.804323 0.473959 0.035 Uiso 1 1 calc R U . . .
H10B H 0.216981 0.826288 0.402488 0.035 Uiso 1 1 calc R U . . .
C11 C 0.2858(2) 0.91742(19) 0.4541(2) 0.0335(8) Uani 1 1 d . . . . .
H11A H 0.340066 0.928373 0.471381 0.040 Uiso 1 1 calc R U . . .
H11B H 0.257615 0.950201 0.400568 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2623(2) 0.93349(19) 0.5393(2) 0.0313(7) Uani 1 1 d . . . . .
H12A H 0.208649 0.919877 0.522586 0.038 Uiso 1 1 calc R U . B 2
H12B H 0.266452 0.986998 0.551635 0.038 Uiso 1 1 calc R U . B 2
S13 S 0.31589(5) 0.88688(5) 0.64679(6) 0.0326(2) Uani 1 1 d . . . C 2
O14 O 0.39422(16) 0.8997(2) 0.6563(2) 0.0594(9) Uani 1 1 d . . . . .
O15 O 0.29741(15) 0.92235(15) 0.72207(17) 0.0407(6) Uani 1 1 d . . . . .
O16 O 0.2959(2) 0.81043(16) 0.6347(2) 0.0606(9) Uani 1 1 d . . . . .
C17 C 0.2738(2) 0.8414(2) 0.0874(2) 0.0325(8) Uani 1 1 d . . . . .
C18 C 0.2013(2) 0.8321(2) 0.0230(3) 0.0378(8) Uani 1 1 d . . . . .
H18 H 0.162627 0.815943 0.045039 0.045 Uiso 1 1 calc R U . . .
C19 C 0.1848(2) 0.8463(2) -0.0735(3) 0.0449(10) Uani 1 1 d . . . . .
H19 H 0.134676 0.840351 -0.116983 0.054 Uiso 1 1 calc R U . . .
C20 C 0.2401(3) 0.8689(2) -0.1066(3) 0.0464(10) Uani 1 1 d . . . . .
H20 H 0.228641 0.877866 -0.172880 0.056 Uiso 1 1 calc R U . . .
C21 C 0.3123(3) 0.8785(2) -0.0434(3) 0.0480(10) Uani 1 1 d . . . . .
H21 H 0.350536 0.894337 -0.066361 0.058 Uiso 1 1 calc R U . . .
C22 C 0.3300(2) 0.8654(2) 0.0533(3) 0.0411(9) Uani 1 1 d . . . . .
H22 H 0.379999 0.872683 0.096379 0.049 Uiso 1 1 calc R U . . .
C23 C 0.18072(18) 0.87738(18) 0.2164(2) 0.0251(7) Uani 1 1 d . . . . .
C24 C 0.11732(19) 0.83540(18) 0.2073(2) 0.0275(7) Uani 1 1 d . . . . .
H24 H 0.121967 0.784774 0.223597 0.033 Uiso 1 1 calc R U . . .
C25 C 0.04728(19) 0.8688(2) 0.1739(2) 0.0304(7) Uani 1 1 d . . . . .
H25 H 0.003027 0.841412 0.166872 0.036 Uiso 1 1 calc R U . . .
C26 C 0.04272(19) 0.9425(2) 0.1510(2) 0.0312(7) Uani 1 1 d . . . . .
C27 C 0.1057(2) 0.9842(2) 0.1612(3) 0.0336(8) Uani 1 1 d . . . . .
H27 H 0.100970 1.034941 0.145780 0.040 Uiso 1 1 calc R U . . .
C28 C 0.17577(19) 0.95140(19) 0.1942(2) 0.0294(7) Uani 1 1 d . . . . .
H28 H 0.219846 0.979172 0.201430 0.035 Uiso 1 1 calc R U . . .
BR29 Br -0.05329(2) 0.98882(3) 0.10553(3) 0.04704(17) Uani 1 1 d . . . . .
O30 O 0.3903(3) 0.9656(3) 0.3297(4) 0.097(2) Uani 0.968(14) 1 d . . . . .
O31 O 0.500000 0.7844(2) 0.750000 0.0483(10) Uani 1 2 d S T P . .
O32A O 0.500000 1.000000 0.500000 0.034(3) Uiso 0.46(2) 2 d S . P D 1
O32B O 0.5249(14) 0.9979(10) 0.4266(18) 0.329(11) Uiso 0.768(10) 1 d . . P D 2
O33A O 0.4630(4) 0.9126(4) 0.2784(5) 0.0239(15) Uiso 0.3 1 d . . P E 1
O33B O 0.500000 0.9920(6) 0.250000 0.102(4) Uiso 0.6 2 d S . P F 2
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'
Br Br -0.2901 2.4595 '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
C5 N1 N2 111.3(3) . . ?
C5 N1 C6 130.7(3) . . ?
N2 N1 C6 117.9(3) . . ?
C3 N2 N1 105.5(3) . . ?
N2 C3 N4 109.7(3) . . ?
N2 C3 C17 123.8(3) . . ?
N4 C3 C17 126.5(3) . . ?
C5 N4 C3 107.7(3) . . ?
C5 N4 C23 125.8(3) . . ?
C3 N4 C23 126.4(3) . . ?
N1 C5 N4 105.7(3) . . ?
N1 C5 C10 131.1(3) . . ?
N4 C5 C10 123.1(3) . . ?
C9Bb C6 C8B 114.2(12) . . ?
C9Bb C6 N1 103.9(8) . . ?
C8Bb C6 N1 101.5(7) . . ?
N1 C6 C8A 110.7(3) . . ?
C9Bb C6 C7B 112.1(14) . . ?
C8Bb C6 C7B 113.1(14) . . ?
N1 C6 C7B 111.0(7) . . ?
N1 C6 C9A 109.3(3) . . ?
C8Aa C6 C9A 109.9(4) . . ?
N1 C6 C7A 107.1(3) . . ?
C8Aa C6 C7A 112.2(4) . . ?
C9Aa C6 C7A 107.6(4) . . ?
C5 C10 C11 111.6(3) . . ?
C12 C11 C10 112.7(3) . . ?
C11 C12 S13 114.9(2) . . ?
O16 S13b O15 113.96(18) . . ?
O16 S13b O14 112.4(2) . . ?
O15 S13b O14 111.70(18) . . ?
O16 S13b C12 107.79(18) . . ?
O15 S13b C12 105.68(16) . . ?
O14 S13b C12 104.50(18) . . ?
C18 C17 C22 118.8(3) . . ?
C18 C17 C3 123.3(3) . . ?
C22 C17 C3 117.9(3) . . ?
C17 C18 C19 120.4(4) . . ?
C20 C19 C18 120.5(4) . . ?
C21 C20 C19 119.6(4) . . ?
C20 C21 C22 120.9(4) . . ?
C21 C22 C17 119.7(4) . . ?
C28 C23 C24 121.9(3) . . ?
C28 C23 N4 118.5(3) . . ?
C24 C23 N4 119.5(3) . . ?
C25 C24 C23 118.7(3) . . ?
C26 C25 C24 119.0(3) . . ?
C27 C26 C25 122.1(3) . . ?
C27 C26 BR29 118.6(3) . . ?
C25 C26 BR29 119.3(3) . . ?
C26 C27 C28 119.3(3) . . ?
C27 C28 C23 118.8(3) . . ?
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
N1 C5 1.326(4) . ?
N1 N2 1.374(4) . ?
N1 C6 1.509(4) . ?
N2 C3 1.303(4) . ?
C3 N4 1.378(4) . ?
C3 C17 1.460(5) . ?
N4 C5 1.352(4) . ?
N4 C23 1.448(4) . ?
C5 C10 1.493(4) . ?
C6 C9B 1.434(17) . ?
C6 C8B 1.514(17) . ?
C6 C8A 1.509(7) . ?
C6 C7B 1.517(18) . ?
C6 C9A 1.541(6) . ?
C6 C7A 1.554(7) . ?
C10 C11 1.536(5) . ?
C11 C12 1.517(5) . ?
C12 S13 1.785(3) . ?
S13b O16 1.438(3) . ?
S13b O15 1.442(3) . ?
S13b O14 1.460(3) . ?
C17 C18 1.383(5) . ?
C17 C22 1.403(5) . ?
C18 C19 1.387(5) . ?
C19 C20 1.371(6) . ?
C20 C21 1.374(6) . ?
C21 C22 1.382(5) . ?
C23 C28 1.384(5) . ?
C23 C24 1.391(4) . ?
C24 C25 1.385(5) . ?
C25 C26 1.380(5) . ?
C26 C27 1.378(5) . ?
C26 BR29 1.903(3) . ?
C27 C28 1.380(5) . ?
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
C5 N1 N2 C3 0.4(4) . . . . ?
C6 N1 N2 C3 177.9(3) . . . . ?
N1 N2 C3 N4 -1.4(4) . . . . ?
N1 N2 C3 C17 177.9(3) . . . . ?
N2 C3 N4 C5 1.9(4) . . . . ?
C17 C3 N4 C5 -177.3(3) . . . . ?
N2 C3 N4 C23 179.7(3) . . . . ?
C17 C3 N4 C23 0.5(5) . . . . ?
N2 N1 C5 N4 0.8(4) . . . . ?
C6 N1 C5 N4 -176.4(3) . . . . ?
N2 N1 C5 C10 -175.7(3) . . . . ?
C6 N1 C5 C10 7.2(6) . . . . ?
C3 N4 C5 N1 -1.6(4) . . . . ?
C23 N4 C5 N1 -179.4(3) . . . . ?
C3 N4 C5 C10 175.2(3) . . . . ?
C23 N4 C5 C10 -2.6(5) . . . . ?
C5 N1 C6 C9Bb 116.8(9) . . . . ?
N2 N1 C6 C9Bb -60.2(9) . . . . ?
C5 N1 C6 C8Bb -124.4(10) . . . . ?
N2 N1 C6 C8Bb 58.6(10) . . . . ?
C5 N1 C6 C8Aa -61.0(5) . . . . ?
N2 N1 C6 C8Aa 122.0(4) . . . . ?
C5 N1 C6 C7Bb -3.9(13) . . . . ?
N2 N1 C6 C7Bb 179.1(13) . . . . ?
C5 N1 C6 C9Aa 177.9(5) . . . . ?
N2 N1 C6 C9Aa 0.8(5) . . . . ?
C5 N1 C6 C7Aa 61.6(5) . . . . ?
N2 N1 C6 C7Aa -115.5(4) . . . . ?
N1 C5 C10 C11 97.5(4) . . . . ?
N4 C5 C10 C11 -78.4(4) . . . . ?
C5 C10 C11 C12 -179.6(3) . . . . ?
C10 C11 C12 S13b 66.0(4) . . . . ?
C11 C12 S13b O16 -71.2(3) . . . . ?
C11 C12 S13b O15 166.6(3) . . . . ?
C11 C12 S13b O14 48.6(3) . . . . ?
N2 C3 C17 C18 140.5(4) . . . . ?
N4 C3 C17 C18 -40.4(6) . . . . ?
N2 C3 C17 C22 -38.5(5) . . . . ?
N4 C3 C17 C22 140.6(4) . . . . ?
C22 C17 C18 C19 0.1(6) . . . . ?
C3 C17 C18 C19 -179.0(4) . . . . ?
C17 C18 C19 C20 0.8(6) . . . . ?
C18 C19 C20 C21 -0.9(6) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C20 C21 C22 C17 0.6(7) . . . . ?
C18 C17 C22 C21 -0.7(6) . . . . ?
C3 C17 C22 C21 178.4(4) . . . . ?
C5 N4 C23 C28 105.3(4) . . . . ?
C3 N4 C23 C28 -72.1(4) . . . . ?
C5 N4 C23 C24 -77.0(4) . . . . ?
C3 N4 C23 C24 105.6(4) . . . . ?
C28 C23 C24 C25 0.7(5) . . . . ?
N4 C23 C24 C25 -176.9(3) . . . . ?
C23 C24 C25 C26 -0.1(5) . . . . ?
C24 C25 C26 C27 -0.7(5) . . . . ?
C24 C25 C26 BR29 -179.8(2) . . . . ?
C25 C26 C27 C28 0.9(5) . . . . ?
BR29 C26 C27 C28 180.0(2) . . . . ?
C26 C27 C28 C23 -0.3(5) . . . . ?
C24 C23 C28 C27 -0.5(5) . . . . ?
N4 C23 C28 C27 177.1(3) . . . . ?
