#------------------------------------------------------------------------------
#$Date: 2021-09-17 04:00:47 +0300 (Fri, 17 Sep 2021) $
#$Revision: 269173 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/35/7243528.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_7243528
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            'C18 H18 Cl F2 N3 O4'
_chemical_formula_weight         413.80
_chemical_melting_point          388
_chemical_name_systematic
'1-Tert-Butyl-3-phenyl-4-(2,4-difluorophenyl)-1,2,4-triazolium perchlorate'
_chemical_properties_physical    Heat-sensitive
_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   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                 92.102(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.248(2)
_cell_length_b                   9.092(2)
_cell_length_c                   20.307(6)
_cell_measurement_temperature    173(2)
_cell_volume                     1890.8(8)
_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 0.996
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18531
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.488
_diffrn_reflns_theta_min         2.007
_exptl_absorpt_coefficient_mu    0.251
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0761
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1148P)²+2.9087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2549
_reflns_number_total             3899
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra04337d2.cif
_cod_data_source_block           ng134
_cod_original_cell_volume        1891.0(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7243528
_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   0.893
_shelx_estimated_absorpt_t_max   0.980
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
CL1A Cl 0.6248(3) 0.0956(4) 0.19603(15) 0.0396(8) Uani 0.669(9) 1 d D . P A 1
O1A O 0.6393(13) 0.2456(7) 0.2112(6) 0.274(9) Uani 0.669(9) 1 d D . P A 1
O2A O 0.5000(6) 0.0380(17) 0.1992(5) 0.247(10) Uani 0.669(9) 1 d D . P A 1
O3A O 0.7082(7) 0.0142(11) 0.2383(3) 0.136(5) Uani 0.669(9) 1 d D . P A 1
O4A O 0.6700(5) 0.0822(6) 0.13033(19) 0.0636(19) Uani 0.669(9) 1 d D . P A 1
CL1B Cl 0.6090(6) 0.1177(7) 0.1865(3) 0.0273(14) Uiso 0.331(9) 1 d D . P A 2
O1B O 0.592(3) 0.230(3) 0.1388(11) 0.31(2) Uiso 0.331(9) 1 d D . P A 2
O2B O 0.577(3) -0.0214(19) 0.1592(14) 0.32(2) Uiso 0.331(9) 1 d D . P A 2
O3B O 0.5213(14) 0.1455(18) 0.2370(6) 0.104(6) Uiso 0.331(9) 1 d D . P A 2
O4B O 0.7389(11) 0.115(4) 0.2120(14) 0.39(4) Uiso 0.331(9) 1 d D . P A 2
C3 C 0.9637(3) 0.7785(4) 0.05047(18) 0.0313(8) Uani 1 1 d . . . . .
C5 C 0.9031(4) 0.8610(4) 0.14604(19) 0.0372(9) Uani 1 1 d . . . . .
H5A H 0.853527 0.886323 0.182995 0.045 Uiso 1 1 calc R U . . .
C6 C 1.1262(4) 0.9506(5) 0.18704(19) 0.0397(10) Uani 1 1 d . . . . .
C7 C 1.2010(4) 1.0669(5) 0.1502(2) 0.0467(11) Uani 1 1 d . . . . .
H7A H 1.246002 1.020750 0.113819 0.070 Uiso 1 1 calc R U . . .
H7B H 1.139996 1.141405 0.132690 0.070 Uiso 1 1 calc R U . . .
H7C H 1.265289 1.113570 0.180422 0.070 Uiso 1 1 calc R U . . .
C8 C 1.2169(6) 0.8259(6) 0.2083(3) 0.0680(16) Uani 1 1 d . . . . .
H8A H 1.260790 0.787512 0.169827 0.102 Uiso 1 1 calc R U . . .
H8B H 1.282226 0.862436 0.240708 0.102 Uiso 1 1 calc R U . . .
H8C H 1.166026 0.747113 0.228065 0.102 Uiso 1 1 calc R U . . .
C9 C 1.0552(5) 1.0152(6) 0.2435(2) 0.0643(15) Uani 1 1 d . . . . .
H9A H 1.118396 1.058363 0.275299 0.096 Uiso 1 1 calc R U . . .
H9B H 0.995037 1.091622 0.226991 0.096 Uiso 1 1 calc R U . . .
H9C H 1.005782 0.937714 0.265037 0.096 Uiso 1 1 calc R U . . .
C10 C 0.7250(3) 0.7516(4) 0.07726(18) 0.0327(8) Uani 1 1 d . . . . .
C11 C 0.6530(4) 0.8296(4) 0.02995(18) 0.0349(9) Uani 1 1 d . . . . .
C12 C 0.5275(4) 0.7924(5) 0.0120(2) 0.0431(10) Uani 1 1 d . . . . .
H12A H 0.478853 0.844996 -0.021070 0.052 Uiso 1 1 calc R U . . .
C13 C 0.4760(4) 0.6750(5) 0.0442(2) 0.0452(11) Uani 1 1 d . . . . .
C14 C 0.5421(4) 0.5954(5) 0.0918(2) 0.0493(11) Uani 1 1 d . . . . .
H14A H 0.501521 0.514699 0.112647 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6695(4) 0.6348(5) 0.1091(2) 0.0416(10) Uani 1 1 d . . . . .
H15A H 0.717724 0.582052 0.142207 0.050 Uiso 1 1 calc R U . . .
C18 C 0.9666(3) 0.7090(4) -0.01457(18) 0.0326(8) Uani 1 1 d . . . . .
C19 C 0.8748(4) 0.6060(4) -0.03607(18) 0.0343(8) Uani 1 1 d . . . . .
H19A H 0.804387 0.580889 -0.009069 0.041 Uiso 1 1 calc R U . . .
C20 C 0.8861(4) 0.5397(5) -0.09720(19) 0.0388(9) Uani 1 1 d . . . . .
H20A H 0.822110 0.470719 -0.112323 0.047 Uiso 1 1 calc R U . . .
C21 C 0.9891(4) 0.5730(5) -0.1360(2) 0.0431(10) Uani 1 1 d . . . . .
H21A H 0.996420 0.527384 -0.177746 0.052 Uiso 1 1 calc R U . . .
C22 C 1.0824(4) 0.6736(5) -0.1137(2) 0.0441(10) Uani 1 1 d . . . . .
H22A H 1.154527 0.695383 -0.140118 0.053 Uiso 1 1 calc R U . . .
C23 C 1.0713(4) 0.7424(5) -0.05374(19) 0.0392(9) Uani 1 1 d . . . . .
H23A H 1.134918 0.812350 -0.039142 0.047 Uiso 1 1 calc R U . . .
F16 F 0.7098(2) 0.9443(3) 0.00107(12) 0.0476(6) Uani 1 1 d . . . . .
F17 F 0.3520(2) 0.6353(4) 0.02726(16) 0.0689(9) Uani 1 1 d . . . . .
N1 N 1.0270(3) 0.8854(4) 0.13923(15) 0.0350(7) Uani 1 1 d . . . . .
N2 N 1.0680(3) 0.8354(4) 0.08006(15) 0.0358(8) Uani 1 1 d . . . . .
N4 N 0.8586(3) 0.7929(4) 0.09055(15) 0.0334(7) Uani 1 1 d . . . . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O2Aa CL1Aa O3A 108.4(6) . . ?
O2Aa CL1Aa O1A 116.6(7) . . ?
O3Aa CL1Aa O1A 108.8(7) . . ?
O2Aa CL1Aa O4A 109.9(5) . . ?
O3Aa CL1Aa O4A 108.3(4) . . ?
O1Aa CL1Aa O4A 104.6(5) . . ?
O3Bb CL1Bb O4B 110.7(9) . . ?
O3Bb CL1Bb O1B 107.6(9) . . ?
O4Bb CL1Bb O1B 110.7(9) . . ?
O3Bb CL1Bb O2B 107.4(9) . . ?
O4Bb CL1Bb O2B 109.5(9) . . ?
O1Bb CL1Bb O2B 110.8(9) . . ?
N2 C3 N4 109.4(3) . . ?
N2 C3 C18 122.6(3) . . ?
N4 C3 C18 127.9(3) . . ?
N1 C5 N4 106.9(3) . . ?
C9 C6 N1 108.2(3) . . ?
C9 C6 C7 111.8(4) . . ?
N1 C6 C7 107.4(3) . . ?
C9 C6 C8 112.6(4) . . ?
N1 C6 C8 106.4(3) . . ?
C7 C6 C8 110.2(4) . . ?
C15 C10 C11 120.1(4) . . ?
C15 C10 N4 121.4(4) . . ?
C11 C10 N4 118.4(3) . . ?
F16 C11 C12 119.7(4) . . ?
F16 C11 C10 118.2(3) . . ?
C12 C11 C10 122.1(4) . . ?
C11 C12 C13 116.2(4) . . ?
F17 C13 C14 118.3(4) . . ?
F17 C13 C12 117.5(4) . . ?
C14 C13 C12 124.2(4) . . ?
C13 C14 C15 118.6(4) . . ?
C10 C15 C14 118.8(4) . . ?
C19 C18 C23 119.7(3) . . ?
C19 C18 C3 122.6(3) . . ?
C23 C18 C3 117.5(3) . . ?
C18 C19 C20 119.8(4) . . ?
C21 C20 C19 120.5(4) . . ?
C20 C21 C22 119.6(4) . . ?
C23 C22 C21 120.6(4) . . ?
C22 C23 C18 119.7(4) . . ?
C5 N1 N2 111.7(3) . . ?
C5 N1 C6 129.7(3) . . ?
N2 N1 C6 118.5(3) . . ?
C3 N2 N1 105.2(3) . . ?
C5 N4 C3 106.7(3) . . ?
C5 N4 C10 124.6(3) . . ?
C3 N4 C10 128.6(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
CL1Aa O2A 1.385(4) . ?
CL1Aa O3A 1.400(4) . ?
CL1Aa O1A 1.405(5) . ?
CL1Aa O4A 1.433(4) . ?
CL1Bb O3B 1.410(5) . ?
CL1Bb O4B 1.412(5) . ?
CL1Bb O1B 1.414(5) . ?
CL1Bb O2B 1.415(5) . ?
C3 N2 1.313(5) . ?
C3 N4 1.380(5) . ?
C3 C18 1.466(5) . ?
C5 N1 1.300(5) . ?
C5 N4 1.351(5) . ?
C6 C9 1.500(6) . ?
C6 N1 1.502(5) . ?
C6 C7 1.519(6) . ?
C6 C8 1.519(6) . ?
C10 C15 1.376(6) . ?
C10 C11 1.385(5) . ?
C10 N4 1.435(5) . ?
C11 F16 1.340(5) . ?
C11 C12 1.366(5) . ?
C12 C13 1.369(6) . ?
C13 F17 1.353(4) . ?
C13 C14 1.367(6) . ?
C14 C15 1.387(6) . ?
C18 C19 1.386(5) . ?
C18 C23 1.393(5) . ?
C19 C20 1.389(5) . ?
C20 C21 1.374(6) . ?
C21 C22 1.387(6) . ?
C22 C23 1.378(6) . ?
N1 N2 1.365(4) . ?
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
C15 C10 C11 F16 178.8(3) . . . . ?
N4 C10 C11 F16 -3.0(5) . . . . ?
C15 C10 C11 C12 -1.7(6) . . . . ?
N4 C10 C11 C12 176.5(3) . . . . ?
F16 C11 C12 C13 -179.3(4) . . . . ?
C10 C11 C12 C13 1.2(6) . . . . ?
C11 C12 C13 F17 -179.7(4) . . . . ?
C11 C12 C13 C14 -0.4(7) . . . . ?
F17 C13 C14 C15 179.4(4) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C11 C10 C15 C14 1.3(6) . . . . ?
N4 C10 C15 C14 -176.8(4) . . . . ?
C13 C14 C15 C10 -0.6(6) . . . . ?
N2 C3 C18 C19 156.6(4) . . . . ?
N4 C3 C18 C19 -21.8(6) . . . . ?
N2 C3 C18 C23 -19.2(5) . . . . ?
N4 C3 C18 C23 162.4(4) . . . . ?
C23 C18 C19 C20 -1.6(6) . . . . ?
C3 C18 C19 C20 -177.3(3) . . . . ?
C18 C19 C20 C21 1.4(6) . . . . ?
C19 C20 C21 C22 0.0(6) . . . . ?
C20 C21 C22 C23 -1.2(7) . . . . ?
C21 C22 C23 C18 1.0(6) . . . . ?
C19 C18 C23 C22 0.5(6) . . . . ?
C3 C18 C23 C22 176.4(4) . . . . ?
N4 C5 N1 N2 0.1(4) . . . . ?
N4 C5 N1 C6 -176.4(4) . . . . ?
C9 C6 N1 C5 -11.3(6) . . . . ?
C7 C6 N1 C5 -132.1(4) . . . . ?
C8 C6 N1 C5 109.9(5) . . . . ?
C9 C6 N1 N2 172.5(4) . . . . ?
C7 C6 N1 N2 51.6(5) . . . . ?
C8 C6 N1 N2 -66.4(5) . . . . ?
N4 C3 N2 N1 0.1(4) . . . . ?
C18 C3 N2 N1 -178.6(3) . . . . ?
C5 N1 N2 C3 -0.1(4) . . . . ?
C6 N1 N2 C3 176.8(3) . . . . ?
N1 C5 N4 C3 0.0(4) . . . . ?
N1 C5 N4 C10 -177.6(3) . . . . ?
N2 C3 N4 C5 0.0(4) . . . . ?
C18 C3 N4 C5 178.5(4) . . . . ?
N2 C3 N4 C10 177.4(4) . . . . ?
C18 C3 N4 C10 -4.0(6) . . . . ?
C15 C10 N4 C5 -73.4(5) . . . . ?
C11 C10 N4 C5 108.4(4) . . . . ?
C15 C10 N4 C3 109.5(5) . . . . ?
C11 C10 N4 C3 -68.6(5) . . . . ?
