#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:46:08 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281337 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/80/1568034.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_1568034
loop_
_publ_author_name
'Duan, Zhuan'
'Young, Claire M.'
'Zhu, Jiayun'
'Slawin, Alexandra M. Z.'
'O'Donoghue, AnnMarie C'
'Smith, Andrew D.'
_publ_section_title
;
 Rate and equilibrium constants for the addition of triazolium salt
 derived N-heterocyclic carbenes to heteroaromatic aldehydes.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              162
_journal_page_last               170
_journal_paper_doi               10.1039/d2sc05704b
_journal_volume                  14
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 B Br F4 N4 O'
_chemical_formula_sum            'C17 H16 B Br F4 N4 O'
_chemical_formula_weight         459.05
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-09-26
_audit_creation_method           'by CrystalStructure 4.3'
_audit_update_record
;
2022-09-26 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.7229(6)
_cell_length_b                   11.8712(8)
_cell_length_c                   15.4592(10)
_cell_measurement_reflns_used    2359
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.70
_cell_volume                     1784.3(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18551
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.163
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             920.00
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.41
_refine_ls_abs_structure_details
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0626
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3220
_reflns_number_total             4098
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d2sc05704b2.cif
_cod_data_source_block           13
_cod_depositor_comments          'Adding full bibliography for 1568034.cif.'
_cod_database_code               1568034
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-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
Br17 Br 0.50498(5) 0.48412(3) 0.09377(2) 0.03326(11) Uani 1 1 d . . . . .
F1 F 0.0843(4) 0.4614(3) 0.3672(2) 0.0744(10) Uani 1 1 d . . . . .
F2 F -0.0353(3) 0.6183(2) 0.3832(2) 0.0621(8) Uani 1 1 d . . . . .
F3 F -0.1431(3) 0.4634(3) 0.3349(2) 0.0741(10) Uani 1 1 d . . . . .
F4 F 0.0096(3) 0.5525(3) 0.24954(16) 0.0706(9) Uani 1 1 d . . . . .
O15 O 0.2668(3) 0.6145(2) 0.20717(16) 0.0286(6) Uani 1 1 d D . . . .
N1 N 0.3513(3) 0.5724(2) 0.43327(17) 0.0183(6) Uani 1 1 d . . . . .
N2 N 0.2963(3) 0.6347(3) 0.5006(2) 0.0223(7) Uani 1 1 d . . . . .
N7 N 0.2559(3) 0.7137(2) 0.37365(18) 0.0204(7) Uani 1 1 d . . . . .
N21 N 0.5537(3) 0.7081(3) 0.2959(2) 0.0263(7) Uani 1 1 d . . . . .
C3 C 0.2399(4) 0.7198(3) 0.4609(2) 0.0221(8) Uani 1 1 d . . . . .
C4 C 0.1643(4) 0.8236(3) 0.4863(3) 0.0310(10) Uani 1 1 d . . . . .
H4A H 0.226202 0.878785 0.514377 0.037 Uiso 1 1 calc R U . . .
H4B H 0.087101 0.806115 0.525795 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1116(4) 0.8678(3) 0.3983(3) 0.0335(9) Uani 1 1 d . . . . .
H5A H 0.012280 0.851439 0.392017 0.040 Uiso 1 1 calc R U . . .
H5B H 0.124845 0.950383 0.394675 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1934(4) 0.8087(3) 0.3261(3) 0.0298(9) Uani 1 1 d . . . . .
H6A H 0.132198 0.781850 0.279228 0.036 Uiso 1 1 calc R U . . .
H6B H 0.264497 0.858940 0.301280 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3272(3) 0.6201(3) 0.3564(2) 0.0184(7) Uani 1 1 d . . . . .
C9 C 0.4199(3) 0.4685(3) 0.4529(2) 0.0191(7) Uani 1 1 d . . . . .
C10 C 0.3699(4) 0.4036(3) 0.5202(2) 0.0230(8) Uani 1 1 d . . . . .
H10 H 0.290463 0.426342 0.551384 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4380(4) 0.3048(3) 0.5411(3) 0.0263(8) Uani 1 1 d . . . . .
H11 H 0.406247 0.260375 0.588161 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5517(4) 0.2700(3) 0.4944(3) 0.0259(8) Uani 1 1 d . . . . .
H12 H 0.596554 0.201416 0.508582 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5997(4) 0.3359(3) 0.4268(2) 0.0273(9) Uani 1 1 d . . . . .
H13 H 0.676889 0.311497 0.394076 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5363(3) 0.4365(3) 0.4066(3) 0.0231(8) Uani 1 1 d . . . . .
H14 H 0.571497 0.483125 0.361867 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3662(4) 0.5789(3) 0.2680(2) 0.0212(8) Uani 1 1 d . . . . .
H15 H 0.372607 0.494794 0.267995 0.025 Uiso 1 1 calc R U . . .
C16 C 0.5043(4) 0.6297(2) 0.24239(19) 0.0211(6) Uani 1 1 d . . . . .
C17 C 0.5733(4) 0.5974(3) 0.1677(2) 0.0242(8) Uani 1 1 d . . . . .
C18 C 0.6964(4) 0.6503(3) 0.1473(3) 0.0309(9) Uani 1 1 d . . . . .
H18 H 0.744915 0.630887 0.096122 0.037 Uiso 1 1 calc R U . . .
C19 C 0.7467(4) 0.7310(3) 0.2021(3) 0.0338(10) Uani 1 1 d . . . . .
H19 H 0.830393 0.768782 0.189317 0.041 Uiso 1 1 calc R U . . .
C20 C 0.6744(4) 0.7563(3) 0.2757(3) 0.0311(9) Uani 1 1 d . . . . .
H20 H 0.711455 0.810611 0.314335 0.037 Uiso 1 1 calc R U . . .
B1 B -0.0240(5) 0.5219(4) 0.3339(3) 0.0358(11) Uani 1 1 d . . . . .
H15O H 0.179(2) 0.581(3) 0.223(3) 0.051(14) Uiso 1 1 d 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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
C15 O15 H15O 108(3) . . ?
C8 N1 N2 112.0(3) . . ?
C8 N1 C9 129.3(3) . . ?
N2 N1 C9 118.7(3) . . ?
C3 N2 N1 102.9(3) . . ?
C8 N7 C3 107.5(3) . . ?
C8 N7 C6 138.5(3) . . ?
C3 N7 C6 114.0(3) . . ?
C16 N21 C20 117.9(3) . . ?
N2 C3 N7 112.2(3) . . ?
N2 C3 C4 136.6(3) . . ?
N7 C3 C4 111.2(3) . . ?
C3 C4 C5 102.3(3) . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
C5 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C6 C5 C4 108.2(3) . . ?
C6 C5 H5A 110.1 . . ?
C4 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
C4 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
N7 C6 C5 101.5(3) . . ?
N7 C6 H6A 111.5 . . ?
C5 C6 H6A 111.5 . . ?
N7 C6 H6B 111.5 . . ?
C5 C6 H6B 111.5 . . ?
H6A C6 H6B 109.3 . . ?
N7 C8 N1 105.4(3) . . ?
N7 C8 C15 125.7(3) . . ?
N1 C8 C15 128.8(3) . . ?
C10 C9 C14 121.3(3) . . ?
C10 C9 N1 118.4(3) . . ?
C14 C9 N1 120.3(3) . . ?
C9 C10 C11 118.7(3) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 118.9(3) . . ?
C13 C14 H14 120.5 . . ?
C9 C14 H14 120.5 . . ?
O15 C15 C8 109.6(3) . . ?
O15 C15 C16 108.1(3) . . ?
C8 C15 C16 109.3(3) . . ?
O15 C15 H15 109.9 . . ?
C8 C15 H15 109.9 . . ?
C16 C15 H15 109.9 . . ?
N21 C16 C17 122.3(4) . . ?
N21 C16 C15 115.6(3) . . ?
C17 C16 C15 122.1(3) . . ?
C18 C17 C16 118.6(4) . . ?
C18 C17 Br17 119.3(3) . . ?
C16 C17 Br17 122.1(3) . . ?
C19 C18 C17 119.0(4) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 118.9(4) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N21 C20 C19 123.2(4) . . ?
N21 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
F3 B1 F1 112.6(4) . . ?
F3 B1 F2 110.6(4) . . ?
F1 B1 F2 106.7(4) . . ?
F3 B1 F4 110.2(4) . . ?
F1 B1 F4 107.9(4) . . ?
F2 B1 F4 108.6(4) . . ?
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
Br17 C17 1.885(4) . ?
F1 B1 1.374(6) . ?
F2 B1 1.379(5) . ?
F3 B1 1.350(5) . ?
F4 B1 1.393(5) . ?
O15 C15 1.413(4) . ?
O15 H15O 0.974(7) . ?
N1 C8 1.337(4) . ?
N1 N2 1.384(4) . ?
N1 C9 1.435(4) . ?
N2 C3 1.302(5) . ?
N7 C8 1.337(4) . ?
N7 C3 1.360(4) . ?
N7 C6 1.477(5) . ?
N21 C16 1.334(4) . ?
N21 C20 1.342(5) . ?
C3 C4 1.488(5) . ?
C4 C5 1.545(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.541(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C15 1.501(5) . ?
C9 C10 1.382(5) . ?
C9 C14 1.392(5) . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.524(5) . ?
C15 H15 1.0000 . ?
C16 C17 1.390(5) . ?
C17 C18 1.388(5) . ?
C18 C19 1.369(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O15 H15o F4 . . . 2.688(4) 0.97(3) 1.73(3) 167(3) no
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
C8 N1 N2 C3 -0.1(4) . . . . ?
C9 N1 N2 C3 -178.3(3) . . . . ?
N1 N2 C3 N7 0.3(4) . . . . ?
N1 N2 C3 C4 -178.3(4) . . . . ?
C8 N7 C3 N2 -0.4(4) . . . . ?
C6 N7 C3 N2 -180.0(3) . . . . ?
C8 N7 C3 C4 178.5(3) . . . . ?
C6 N7 C3 C4 -1.0(5) . . . . ?
N2 C3 C4 C5 -170.5(4) . . . . ?
N7 C3 C4 C5 10.9(4) . . . . ?
C3 C4 C5 C6 -16.4(4) . . . . ?
C8 N7 C6 C5 171.3(4) . . . . ?
C3 N7 C6 C5 -9.4(4) . . . . ?
C4 C5 C6 N7 15.7(4) . . . . ?
C3 N7 C8 N1 0.4(4) . . . . ?
C6 N7 C8 N1 179.7(4) . . . . ?
C3 N7 C8 C15 178.8(3) . . . . ?
C6 N7 C8 C15 -1.9(7) . . . . ?
N2 N1 C8 N7 -0.2(4) . . . . ?
C9 N1 C8 N7 177.8(3) . . . . ?
N2 N1 C8 C15 -178.6(3) . . . . ?
C9 N1 C8 C15 -0.5(6) . . . . ?
C8 N1 C9 C10 -142.8(4) . . . . ?
N2 N1 C9 C10 35.2(4) . . . . ?
C8 N1 C9 C14 39.1(5) . . . . ?
N2 N1 C9 C14 -142.9(3) . . . . ?
C14 C9 C10 C11 -0.1(5) . . . . ?
N1 C9 C10 C11 -178.2(3) . . . . ?
C9 C10 C11 C12 -1.6(5) . . . . ?
C10 C11 C12 C13 1.2(5) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C12 C13 C14 C9 -2.7(5) . . . . ?
C10 C9 C14 C13 2.2(5) . . . . ?
N1 C9 C14 C13 -179.8(3) . . . . ?
N7 C8 C15 O15 -29.3(5) . . . . ?
N1 C8 C15 O15 148.7(3) . . . . ?
N7 C8 C15 C16 89.0(4) . . . . ?
N1 C8 C15 C16 -92.9(4) . . . . ?
C20 N21 C16 C17 0.0(5) . . . . ?
C20 N21 C16 C15 -179.3(3) . . . . ?
O15 C15 C16 N21 111.6(3) . . . . ?
C8 C15 C16 N21 -7.6(4) . . . . ?
O15 C15 C16 C17 -67.7(4) . . . . ?
C8 C15 C16 C17 173.0(3) . . . . ?
N21 C16 C17 C18 -1.4(5) . . . . ?
C15 C16 C17 C18 177.9(3) . . . . ?
N21 C16 C17 Br17 178.5(3) . . . . ?
C15 C16 C17 Br17 -2.2(5) . . . . ?
C16 C17 C18 C19 1.1(5) . . . . ?
Br17 C17 C18 C19 -178.8(3) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C16 N21 C20 C19 1.8(6) . . . . ?
C18 C19 C20 N21 -2.0(6) . . . . ?
