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#$Date: 2021-09-17 04:00:47 +0300 (Fri, 17 Sep 2021) $
#$Revision: 269173 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/35/7243531.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_7243531
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 H17 F2 N3'
_chemical_formula_weight         313.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                101.552(4)
_cell_angle_beta                 93.625(4)
_cell_angle_gamma                93.431(4)
_cell_formula_units_Z            2
_cell_length_a                   5.4869(3)
_cell_length_b                   10.1446(6)
_cell_length_c                   14.6445(8)
_cell_measurement_temperature    173(2)
_cell_volume                     794.84(8)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.694
_diffrn_reflns_theta_min         2.247
_exptl_absorpt_coefficient_mu    0.095
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0528
_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)+(0.0638P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1908
_reflns_number_total             3020
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra04337d2.cif
_cod_data_source_block           nk346
_cod_database_code               7243531
_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   0.954
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
F1 F 0.9913(2) 0.40193(13) 0.61260(9) 0.0474(4) Uani 1 1 d . . . . .
F2 F 0.3680(3) 0.33086(14) 0.36977(9) 0.0541(5) Uani 1 1 d . . . . .
N1 N 0.7938(3) 0.19401(17) 0.68737(12) 0.0261(4) Uani 1 1 d . . . . .
N2 N 1.0004(3) 0.09085(17) 0.77212(12) 0.0274(5) Uani 1 1 d . . . . .
N3 N 0.9179(3) 0.19848(18) 0.83435(12) 0.0309(5) Uani 1 1 d . . . . .
C1 C 0.9298(4) 0.0816(2) 0.68120(16) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.7921(4) 0.2615(2) 0.77928(15) 0.0270(5) Uani 1 1 d . . . . .
C3 C 0.6799(4) 0.2299(2) 0.60564(14) 0.0267(5) Uani 1 1 d . . . . .
C4 C 0.7840(4) 0.3329(2) 0.56885(15) 0.0298(5) Uani 1 1 d . . . . .
C5 C 0.6832(4) 0.3684(2) 0.48951(16) 0.0367(6) Uani 1 1 d . . . . .
H5 H 0.757049 0.439246 0.464623 0.044 Uiso 1 1 calc R U . . .
C6 C 0.4717(5) 0.2969(2) 0.44808(15) 0.0350(6) Uani 1 1 d . . . . .
C7 C 0.3584(4) 0.1932(2) 0.48107(16) 0.0366(6) Uani 1 1 d . . . . .
H7 H 0.211625 0.145893 0.450427 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4673(4) 0.1605(2) 0.56102(15) 0.0328(6) Uani 1 1 d . . . . .
H8 H 0.394108 0.089012 0.585435 0.039 Uiso 1 1 calc R U . . .
C9 C 1.1316(4) -0.0118(2) 0.81237(15) 0.0292(5) Uani 1 1 d . . . . .
C10 C 1.2708(5) -0.0931(3) 0.73668(17) 0.0521(8) Uani 1 1 d . . . . .
H10A H 1.357762 -0.160888 0.762238 0.078 Uiso 1 1 calc R U . . .
H10B H 1.155312 -0.138231 0.684413 0.078 Uiso 1 1 calc R U . . .
H10C H 1.389037 -0.032665 0.714563 0.078 Uiso 1 1 calc R U . . .
C11 C 0.9427(4) -0.1022(3) 0.8461(2) 0.0504(7) Uani 1 1 d . . . . .
H11A H 1.024987 -0.170493 0.872807 0.076 Uiso 1 1 calc R U . . .
H11B H 0.852633 -0.047866 0.893882 0.076 Uiso 1 1 calc R U . . .
H11C H 0.828243 -0.146854 0.793340 0.076 Uiso 1 1 calc R U . . .
C12 C 1.3088(4) 0.0611(2) 0.89303(17) 0.0451(7) Uani 1 1 d . . . . .
H12A H 1.396268 -0.005087 0.920130 0.068 Uiso 1 1 calc R U . . .
H12B H 1.426768 0.120859 0.870134 0.068 Uiso 1 1 calc R U . . .
H12C H 1.217687 0.114686 0.940880 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6744(4) 0.3868(2) 0.81483(15) 0.0285(5) Uani 1 1 d . . . . .
C14 C 0.4564(4) 0.4195(2) 0.77365(16) 0.0363(6) Uani 1 1 d . . . . .
H14 H 0.377976 0.360732 0.719699 0.044 Uiso 1 1 calc R U . . .
C15 C 0.3543(5) 0.5382(2) 0.81167(17) 0.0421(7) Uani 1 1 d . . . . .
H15 H 0.206903 0.560947 0.782956 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4642(5) 0.6231(2) 0.89051(17) 0.0421(7) Uani 1 1 d . . . . .
H16 H 0.392285 0.703766 0.916300 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6796(5) 0.5909(2) 0.93219(17) 0.0464(7) Uani 1 1 d . . . . .
H17 H 0.755684 0.648943 0.986907 0.056 Uiso 1 1 calc R U . . .
C18 C 0.7832(4) 0.4741(2) 0.89392(16) 0.0377(6) Uani 1 1 d . . . . .
H18 H 0.932397 0.452996 0.922296 0.045 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'
F F 0.0171 0.0103 '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 N1 C1 110.84(16) . . ?
C2 N1 C3 127.55(16) . . ?
C1 N1 C3 121.60(17) . . ?
C1 N2 N3 116.10(16) . . ?
C1 N2 C9 125.85(17) . . ?
N3 N2 C9 117.61(16) . . ?
C2 N3 N2 103.09(16) . . ?
N2 C1 N1 100.14(17) . . ?
N3 C2 N1 109.82(17) . . ?
N3 C2 C13 122.59(19) . . ?
N1 C2 C13 127.58(18) . . ?
C4 C3 C8 118.5(2) . . ?
C4 C3 N1 120.6(2) . . ?
C8 C3 N1 120.91(19) . . ?
F1 C4 C5 118.9(2) . . ?
F1 C4 C3 118.80(19) . . ?
C5 C4 C3 122.3(2) . . ?
C6 C5 C4 117.0(2) . . ?
F2 C6 C5 118.0(2) . . ?
F2 C6 C7 118.3(2) . . ?
C5 C6 C7 123.7(2) . . ?
C6 C7 C8 117.3(2) . . ?
C3 C8 C7 121.2(2) . . ?
N2 C9 C11 108.09(17) . . ?
N2 C9 C12 108.60(18) . . ?
C11 C9 C12 110.7(2) . . ?
N2 C9 C10 108.68(17) . . ?
C11 C9 C10 110.6(2) . . ?
C12 C9 C10 110.09(19) . . ?
C18 C13 C14 118.69(19) . . ?
C18 C13 C2 118.39(19) . . ?
C14 C13 C2 122.9(2) . . ?
C15 C14 C13 119.8(2) . . ?
C16 C15 C14 120.6(2) . . ?
C15 C16 C17 119.9(2) . . ?
C18 C17 C16 119.6(2) . . ?
C17 C18 C13 121.4(2) . . ?
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
F1 C4 1.352(2) . ?
F2 C6 1.363(2) . ?
N1 C2 1.383(3) . ?
N1 C1 1.390(3) . ?
N1 C3 1.436(2) . ?
N2 C1 1.346(3) . ?
N2 N3 1.393(2) . ?
N2 C9 1.494(3) . ?
N3 C2 1.313(2) . ?
C2 C13 1.476(3) . ?
C3 C4 1.379(3) . ?
C3 C8 1.380(3) . ?
C4 C5 1.377(3) . ?
C5 C6 1.369(3) . ?
C6 C7 1.374(3) . ?
C7 C8 1.389(3) . ?
C9 C11 1.514(3) . ?
C9 C12 1.519(3) . ?
C9 C10 1.519(3) . ?
C13 C18 1.386(3) . ?
C13 C14 1.393(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.375(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.376(3) . ?
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
C1 N2 N3 C2 -1.1(2) . . . . ?
C9 N2 N3 C2 -173.94(18) . . . . ?
N3 N2 C1 N1 0.7(2) . . . . ?
C9 N2 C1 N1 172.84(19) . . . . ?
C2 N1 C1 N2 0.0(2) . . . . ?
C3 N1 C1 N2 178.92(18) . . . . ?
N2 N3 C2 N1 1.0(2) . . . . ?
N2 N3 C2 C13 -178.05(19) . . . . ?
C1 N1 C2 N3 -0.7(3) . . . . ?
C3 N1 C2 N3 -179.5(2) . . . . ?
C1 N1 C2 C13 178.3(2) . . . . ?
C3 N1 C2 C13 -0.5(4) . . . . ?
C2 N1 C3 C4 76.9(3) . . . . ?
C1 N1 C3 C4 -101.9(2) . . . . ?
C2 N1 C3 C8 -104.6(3) . . . . ?
C1 N1 C3 C8 76.7(3) . . . . ?
C8 C3 C4 F1 179.55(18) . . . . ?
N1 C3 C4 F1 -1.9(3) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
N1 C3 C4 C5 178.57(18) . . . . ?
F1 C4 C5 C6 -179.25(19) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 F2 179.61(18) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
F2 C6 C7 C8 -179.94(18) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C4 C3 C8 C7 -0.3(3) . . . . ?
N1 C3 C8 C7 -178.91(18) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C1 N2 C9 C11 -95.0(3) . . . . ?
N3 N2 C9 C11 77.1(2) . . . . ?
C1 N2 C9 C12 144.8(2) . . . . ?
N3 N2 C9 C12 -43.1(2) . . . . ?
C1 N2 C9 C10 25.1(3) . . . . ?
N3 N2 C9 C10 -162.83(19) . . . . ?
N3 C2 C13 C18 31.0(3) . . . . ?
N1 C2 C13 C18 -147.9(2) . . . . ?
N3 C2 C13 C14 -147.5(2) . . . . ?
N1 C2 C13 C14 33.6(3) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C2 C13 C14 C15 179.0(2) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C14 C13 C18 C17 0.4(4) . . . . ?
C2 C13 C18 C17 -178.2(2) . . . . ?
