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#$Date: 2020-09-06 11:12:44 +0300 (Sun, 06 Sep 2020) $
#$Revision: 255952 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/68/7126800.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_7126800
loop_
_publ_author_name
'Appel, Sebastian'
'Brüggemann, Peter'
'Ganter, Christian'
_publ_section_title
;
 A tropylium annulated N-heterocyclic carbene.
;
_journal_issue                   63
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9020
_journal_page_last               9023
_journal_paper_doi               10.1039/d0cc04482b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C10 H11 N2 Se,B F4'
_chemical_formula_sum            'C10 H11 B F4 N2 Se'
_chemical_formula_weight         324.98
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-03-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.965(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1299(18)
_cell_length_b                   6.2796(10)
_cell_length_c                   16.088(3)
_cell_measurement_reflns_used    6921
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      26.5115
_cell_measurement_theta_min      2.542
_cell_volume                     1220.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12836
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.196
_diffrn_reflns_theta_min         2.197
_exptl_absorpt_coefficient_mu    3.107
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.550
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0506
_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)+(0.0630P)²+4.3211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2021
_reflns_number_total             2422
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc04482b2.cif
_cod_data_source_block           mo_SA_458_2_3-auto
_cod_depositor_comments
'Adding full bibliography for 7126798--7126803.cif.'
_cod_original_cell_volume        1220.8(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7126800
_shelx_shelxl_version_number     2014/7
_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   0.575
_shelx_estimated_absorpt_t_max   0.860
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
Se1 Se 0.92751(4) 0.20892(8) 0.47186(4) 0.0386(2) Uani 1 1 d . . . . .
F1 F 0.5297(3) 0.3312(6) 0.2650(2) 0.0659(12) Uani 1 1 d . . . . .
F2 F 0.3669(3) 0.4964(7) 0.2709(2) 0.0627(11) Uani 1 1 d . . . . .
F3 F 0.5211(4) 0.6872(6) 0.2692(2) 0.0714(13) Uani 1 1 d . . . . .
F4 F 0.4931(3) 0.4945(5) 0.38256(18) 0.0538(9) Uani 1 1 d . . . . .
N1 N 0.8243(3) 0.5388(6) 0.5589(2) 0.0229(8) Uani 1 1 d . . . . .
N2 N 0.7944(3) 0.5676(6) 0.4228(2) 0.0230(8) Uani 1 1 d . . . . .
C1 C 0.8474(3) 0.4436(7) 0.4852(3) 0.0256(9) Uani 1 1 d . . . . .
C2 C 0.8002(4) 0.5250(9) 0.3333(3) 0.0388(12) Uani 1 1 d . . . . .
H2A H 0.7252 0.5157 0.3057 0.058 Uiso 1 1 calc R U . . .
H2B H 0.8390 0.3901 0.3264 0.058 Uiso 1 1 calc R U . . .
H2C H 0.8404 0.6407 0.3084 0.058 Uiso 1 1 calc R U . . .
C3 C 0.8681(4) 0.4644(9) 0.6416(3) 0.0353(11) Uani 1 1 d . . . . .
H3A H 0.9090 0.3314 0.6359 0.053 Uiso 1 1 calc R U . . .
H3B H 0.8067 0.4395 0.6762 0.053 Uiso 1 1 calc R U . . .
H3C H 0.9178 0.5725 0.6680 0.053 Uiso 1 1 calc R U . . .
C4 C 0.7619(3) 0.7181(7) 0.5437(3) 0.0214(9) Uani 1 1 d . . . . .
C5 C 0.7282(4) 0.8527(8) 0.6052(3) 0.0290(10) Uani 1 1 d . . . . .
H5 H 0.7489 0.8143 0.6616 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6676(4) 1.0364(8) 0.5920(3) 0.0365(12) Uani 1 1 d . . . . .
H6 H 0.6537 1.1118 0.6412 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6236(4) 1.1289(8) 0.5184(4) 0.0395(13) Uani 1 1 d . . . . .
H7 H 0.5835 1.2569 0.5248 0.047 Uiso 1 1 calc R U . . .
C8 C 0.6293(4) 1.0628(8) 0.4371(4) 0.0365(12) Uani 1 1 d . . . . .
H8 H 0.5916 1.1501 0.3956 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6823(4) 0.8871(8) 0.4081(3) 0.0299(10) Uani 1 1 d . . . . .
H9 H 0.6773 0.8685 0.3492 0.036 Uiso 1 1 calc R U . . .
C10 C 0.7420(3) 0.7349(7) 0.4550(3) 0.0220(9) Uani 1 1 d . . . . .
B1 B 0.4783(4) 0.5015(8) 0.2964(3) 0.0266(11) 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'
B B 0.0013 0.0007 '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'
Se Se -0.0929 2.2259 '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
C4 N1 C1 110.8(4) . . ?
C4 N1 C3 125.2(4) . . ?
C1 N1 C3 123.9(4) . . ?
C10 N2 C1 111.3(3) . . ?
C10 N2 C2 125.4(4) . . ?
C1 N2 C2 123.2(4) . . ?
N1 C1 N2 105.3(4) . . ?
N1 C1 Se1 127.8(3) . . ?
N2 C1 Se1 126.9(3) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 124.5(4) . . ?
N1 C4 C10 106.3(4) . . ?
C5 C4 C10 129.1(4) . . ?
C6 C5 C4 125.9(5) . . ?
C6 C5 H5 117.1 . . ?
C4 C5 H5 117.1 . . ?
C5 C6 C7 130.3(5) . . ?
C5 C6 H6 114.8 . . ?
C7 C6 H6 114.8 . . ?
C8 C7 C6 129.6(5) . . ?
C8 C7 H7 115.2 . . ?
C6 C7 H7 115.2 . . ?
C7 C8 C9 128.7(5) . . ?
C7 C8 H8 115.7 . . ?
C9 C8 H8 115.7 . . ?
C8 C9 C10 127.2(5) . . ?
C8 C9 H9 116.4 . . ?
C10 C9 H9 116.4 . . ?
N2 C10 C9 124.6(4) . . ?
N2 C10 C4 106.3(4) . . ?
C9 C10 C4 129.1(4) . . ?
F1 B1 F3 110.7(5) . . ?
F1 B1 F2 109.9(4) . . ?
F3 B1 F2 108.3(4) . . ?
F1 B1 F4 108.9(4) . . ?
F3 B1 F4 109.2(4) . . ?
F2 B1 F4 109.8(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
Se1 C1 1.788(5) . ?
F1 B1 1.358(6) . ?
F2 B1 1.378(6) . ?
F3 B1 1.364(6) . ?
F4 B1 1.382(6) . ?
N1 C4 1.367(6) . ?
N1 C1 1.379(6) . ?
N1 C3 1.466(6) . ?
N2 C10 1.354(6) . ?
N2 C1 1.384(6) . ?
N2 C2 1.471(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.390(6) . ?
C4 C10 1.431(6) . ?
C5 C6 1.374(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(7) . ?
C9 H9 0.9500 . ?
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
C4 N1 C1 N2 -1.5(5) . . . . ?
C3 N1 C1 N2 -177.5(4) . . . . ?
C4 N1 C1 Se1 179.0(3) . . . . ?
C3 N1 C1 Se1 3.1(6) . . . . ?
C10 N2 C1 N1 1.1(5) . . . . ?
C2 N2 C1 N1 178.3(4) . . . . ?
C10 N2 C1 Se1 -179.4(3) . . . . ?
C2 N2 C1 Se1 -2.2(6) . . . . ?
C1 N1 C4 C5 -177.8(4) . . . . ?
C3 N1 C4 C5 -2.0(7) . . . . ?
C1 N1 C4 C10 1.4(5) . . . . ?
C3 N1 C4 C10 177.3(4) . . . . ?
N1 C4 C5 C6 178.5(4) . . . . ?
C10 C4 C5 C6 -0.6(8) . . . . ?
C4 C5 C6 C7 1.9(8) . . . . ?
C5 C6 C7 C8 -0.7(9) . . . . ?
C6 C7 C8 C9 -1.0(9) . . . . ?
C7 C8 C9 C10 0.4(8) . . . . ?
C1 N2 C10 C9 179.8(4) . . . . ?
C2 N2 C10 C9 2.6(7) . . . . ?
C1 N2 C10 C4 -0.3(5) . . . . ?
C2 N2 C10 C4 -177.4(4) . . . . ?
C8 C9 C10 N2 -178.6(4) . . . . ?
C8 C9 C10 C4 1.4(8) . . . . ?
N1 C4 C10 N2 -0.7(4) . . . . ?
C5 C4 C10 N2 178.5(4) . . . . ?
N1 C4 C10 C9 179.3(4) . . . . ?
C5 C4 C10 C9 -1.5(8) . . . . ?
