#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:17:55 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267021 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/83/7128345.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_7128345
loop_
_publ_author_name
'Liang, Qiuming'
'Hayashi, Kasumi'
'Zeng, Yimin'
'Jimenez-Santiago, Jose L'
'Song, Datong'
_publ_section_title
;
 Constructing fused N-heterocycles from unprotected mesoionic
 N-heterocyclic olefins and organic azides via diazo transfer.
;
_journal_issue                   50
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6137
_journal_page_last               6140
_journal_paper_doi               10.1039/d1cc02245h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C16 H10 F3 N5'
_chemical_formula_weight         329.29
_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-2016/6
_audit_update_record
;
2021-04-08 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                100.422(10)
_cell_angle_beta                 93.394(11)
_cell_angle_gamma                101.959(11)
_cell_formula_units_Z            2
_cell_length_a                   7.229(2)
_cell_length_b                   7.692(2)
_cell_length_c                   13.893(4)
_cell_measurement_reflns_used    25281
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.562
_cell_measurement_theta_min      2.997
_cell_volume                     739.5(4)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25281
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.997
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.051(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0371
_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)+(0.0659P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2403
_reflns_number_total             3376
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02245h2.cif
_cod_data_source_block           wl476
_cod_depositor_comments
'Adding full bibliography for 7128333--7128355.cif.'
_cod_database_code               7128345
_shelx_shelxl_version_number     2016/6
_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   0.976
_shelx_estimated_absorpt_t_max   0.988
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 0.44136(12) 0.68861(13) 0.14645(6) 0.0508(3) Uani 1 1 d . . . . .
N1 N 0.73162(14) 0.25280(12) 0.49866(7) 0.0217(2) Uani 1 1 d . . . . .
C1 C 1.00866(18) 0.79410(18) 0.76258(9) 0.0324(3) Uani 1 1 d . . . . .
H1 H 0.996325 0.895684 0.734726 0.039 Uiso 1 1 calc R U . . .
F2 F 0.30995(12) 0.37601(14) 0.01332(5) 0.0549(3) Uani 1 1 d . . . . .
N2 N 0.64516(14) 0.20627(13) 0.40763(7) 0.0241(2) Uani 1 1 d . . . . .
C2 C 1.0887(2) 0.8206(2) 0.85821(10) 0.0407(4) Uani 1 1 d . . . . .
H2 H 1.131436 0.940338 0.895529 0.049 Uiso 1 1 calc R U . . .
N3 N 0.63104(13) 0.36243(13) 0.38060(7) 0.0212(2) Uani 1 1 d . . . . .
F3 F 0.33178(13) 0.05538(12) 0.06174(6) 0.0588(3) Uani 1 1 d . . . . .
C3 C 1.10745(19) 0.6742(2) 0.90030(10) 0.0413(4) Uani 1 1 d . . . . .
H3 H 1.161299 0.693187 0.966426 0.050 Uiso 1 1 calc R U . . .
N4 N 0.83139(14) 0.73775(13) 0.56755(7) 0.0256(2) Uani 1 1 d . . . . .
C4 C 1.04731(19) 0.5010(2) 0.84547(10) 0.0376(3) Uani 1 1 d . . . . .
H4 H 1.060936 0.400092 0.873670 0.045 Uiso 1 1 calc R U . . .
C5 C 0.96660(18) 0.47325(18) 0.74881(9) 0.0304(3) Uani 1 1 d . . . . .
H5 H 0.925611 0.353228 0.711671 0.037 Uiso 1 1 calc R U . . .
N5 N 0.74088(15) 0.68872(13) 0.47260(7) 0.0250(3) Uani 1 1 d . . . . .
C6 C 0.94526(16) 0.61832(16) 0.70608(8) 0.0240(3) Uani 1 1 d . . . . .
C7 C 0.85465(16) 0.59314(15) 0.60534(8) 0.0206(3) Uani 1 1 d . . . . .
C12 C 0.45606(19) 0.5299(2) 0.17106(10) 0.0348(3) Uani 1 1 d . . . . .
C11 C 0.53702(17) 0.52868(18) 0.26305(9) 0.0285(3) Uani 1 1 d . . . . .
H11 H 0.584608 0.638198 0.309586 0.034 Uiso 1 1 calc R U . . .
C10 C 0.54672(16) 0.36244(17) 0.28542(8) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.70960(16) 0.50771(15) 0.45485(8) 0.0199(3) Uani 1 1 d . . . . .
C8 C 0.77432(15) 0.43662(14) 0.53183(8) 0.0189(3) Uani 1 1 d . . . . .
C13 C 0.38786(19) 0.3721(2) 0.10266(9) 0.0388(4) Uani 1 1 d . . . . .
C15 C 0.47824(18) 0.20016(18) 0.21951(9) 0.0313(3) Uani 1 1 d . . . . .
H15 H 0.484947 0.087257 0.236500 0.038 Uiso 1 1 calc R U . . .
C16 C 0.76902(19) 0.10594(16) 0.54533(10) 0.0312(3) Uani 1 1 d . . . . .
H16A H 0.727346 -0.009839 0.498709 0.047 Uiso 1 1 calc R U . . .
H16B H 0.699252 0.102347 0.603573 0.047 Uiso 1 1 calc R U . . .
H16C H 0.905513 0.126934 0.564984 0.047 Uiso 1 1 calc R U . . .
C14 C 0.40014(19) 0.2095(2) 0.12842(9) 0.0387(4) 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'
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
N2 N1 C8 112.02(9) . . ?
N2 N1 C16 117.00(9) . . ?
C8 N1 C16 130.97(10) . . ?
C2 C1 C6 120.59(13) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
N1 N2 N3 105.78(9) . . ?
C1 C2 C3 120.60(13) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
N2 N3 C9 110.63(9) . . ?
N2 N3 C10 120.72(9) . . ?
C9 N3 C10 128.63(10) . . ?
C4 C3 C2 119.47(13) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C7 N4 N5 112.52(9) . . ?
C3 C4 C5 120.23(13) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.93(13) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C9 N5 N4 102.93(9) . . ?
C5 C6 C1 118.18(12) . . ?
C5 C6 C7 122.20(11) . . ?
C1 C6 C7 119.60(11) . . ?
N4 C7 C8 106.67(10) . . ?
N4 C7 C6 120.34(10) . . ?
C8 C7 C6 132.98(10) . . ?
F1 C12 C11 119.77(13) . . ?
F1 C12 C13 118.52(12) . . ?
C11 C12 C13 121.71(13) . . ?
C12 C11 C10 117.71(13) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C11 C10 C15 122.68(12) . . ?
C11 C10 N3 117.35(11) . . ?
C15 C10 N3 119.97(11) . . ?
N5 C9 N3 139.20(10) . . ?
N5 C9 C8 114.46(10) . . ?
N3 C9 C8 106.33(10) . . ?
N1 C8 C9 105.23(10) . . ?
N1 C8 C7 151.33(10) . . ?
C9 C8 C7 103.42(10) . . ?
F2 C13 C12 120.87(14) . . ?
F2 C13 C14 120.62(13) . . ?
C12 C13 C14 118.51(12) . . ?
C14 C15 C10 117.13(13) . . ?
C14 C15 H15 121.4 . . ?
C10 C15 H15 121.4 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F3 C14 C15 119.34(14) . . ?
F3 C14 C13 118.39(12) . . ?
C15 C14 C13 122.26(13) . . ?
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 C12 1.3488(16) . ?
N1 N2 1.3297(14) . ?
N1 C8 1.3687(15) . ?
N1 C16 1.4630(15) . ?
C1 C2 1.3797(18) . ?
C1 C6 1.4038(19) . ?
C1 H1 0.9500 . ?
F2 C13 1.3402(15) . ?
N2 N3 1.3430(13) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
N3 C9 1.3732(15) . ?
N3 C10 1.4229(15) . ?
F3 C14 1.3467(16) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9500 . ?
N4 C7 1.3488(14) . ?
N4 N5 1.3878(14) . ?
C4 C5 1.3932(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3862(17) . ?
C5 H5 0.9500 . ?
N5 C9 1.3376(15) . ?
C6 C7 1.4718(16) . ?
C7 C8 1.4230(16) . ?
C12 C11 1.3761(17) . ?
C12 C13 1.378(2) . ?
C11 C10 1.3838(17) . ?
C11 H11 0.9500 . ?
C10 C15 1.3850(18) . ?
C9 C8 1.3856(16) . ?
C13 C14 1.380(2) . ?
C15 C14 1.3750(18) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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 N3 0.04(12) . . . . ?
C16 N1 N2 N3 -178.63(9) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
N1 N2 N3 C9 0.23(12) . . . . ?
N1 N2 N3 C10 179.14(9) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C7 N4 N5 C9 0.29(13) . . . . ?
C4 C5 C6 C1 0.53(18) . . . . ?
C4 C5 C6 C7 -177.87(11) . . . . ?
C2 C1 C6 C5 -0.42(19) . . . . ?
C2 C1 C6 C7 178.02(11) . . . . ?
N5 N4 C7 C8 -0.29(13) . . . . ?
N5 N4 C7 C6 -178.99(10) . . . . ?
C5 C6 C7 N4 177.96(10) . . . . ?
C1 C6 C7 N4 -0.42(17) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C1 C6 C7 C8 -178.72(12) . . . . ?
F1 C12 C11 C10 179.15(10) . . . . ?
C13 C12 C11 C10 -0.51(19) . . . . ?
C12 C11 C10 C15 -0.21(18) . . . . ?
C12 C11 C10 N3 179.86(10) . . . . ?
N2 N3 C10 C11 179.90(9) . . . . ?
C9 N3 C10 C11 -1.41(17) . . . . ?
N2 N3 C10 C15 -0.04(17) . . . . ?
C9 N3 C10 C15 178.66(11) . . . . ?
N4 N5 C9 N3 -179.51(14) . . . . ?
N4 N5 C9 C8 -0.18(13) . . . . ?
N2 N3 C9 N5 178.97(13) . . . . ?
C10 N3 C9 N5 0.2(2) . . . . ?
N2 N3 C9 C8 -0.40(13) . . . . ?
C10 N3 C9 C8 -179.20(10) . . . . ?
N2 N1 C8 C9 -0.28(12) . . . . ?
C16 N1 C8 C9 178.15(11) . . . . ?
N2 N1 C8 C7 -178.58(19) . . . . ?
C16 N1 C8 C7 -0.1(3) . . . . ?
N5 C9 C8 N1 -179.15(9) . . . . ?
N3 C9 C8 N1 0.40(12) . . . . ?
N5 C9 C8 C7 0.01(13) . . . . ?
N3 C9 C8 C7 179.56(9) . . . . ?
N4 C7 C8 N1 178.48(19) . . . . ?
C6 C7 C8 N1 -3.1(3) . . . . ?
N4 C7 C8 C9 0.16(12) . . . . ?
C6 C7 C8 C9 178.63(12) . . . . ?
F1 C12 C13 F2 0.53(19) . . . . ?
C11 C12 C13 F2 -179.81(11) . . . . ?
F1 C12 C13 C14 -178.97(11) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C11 C10 C15 C14 0.70(19) . . . . ?
N3 C10 C15 C14 -179.37(10) . . . . ?
C10 C15 C14 F3 179.93(11) . . . . ?
C10 C15 C14 C13 -0.5(2) . . . . ?
F2 C13 C14 F3 -0.10(19) . . . . ?
C12 C13 C14 F3 179.40(12) . . . . ?
F2 C13 C14 C15 -179.67(11) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
