#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:17:55 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267021 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/83/7128349.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_7128349
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            'C20 H21 N5'
_chemical_formula_weight         331.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 91.965(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6431(16)
_cell_length_b                   15.692(2)
_cell_length_c                   13.006(2)
_cell_measurement_reflns_used    38822
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.492
_cell_measurement_theta_min      3.033
_cell_volume                     1762.9(5)
_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 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38822
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.033
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6889
_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    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.025(6)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0718P)²+0.4752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3547
_reflns_number_total             4018
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02245h2.cif
_cod_data_source_block           wl469
_cod_depositor_comments
'Adding full bibliography for 7128333--7128355.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128349
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.25150(10) 0.39707(6) 0.15680(7) 0.0210(2) Uani 1 1 d . . . . .
C1 C 0.16963(14) 0.68607(7) 0.00572(9) 0.0262(3) Uani 1 1 d . . . . .
H1A H 0.174851 0.723457 0.063186 0.031 Uiso 1 1 calc R U . . .
C2 C 0.15996(14) 0.71972(8) -0.09303(9) 0.0293(3) Uani 1 1 d . . . . .
H2A H 0.157933 0.779736 -0.102564 0.035 Uiso 1 1 calc R U . . .
N2 N 0.27400(11) 0.35796(6) 0.24701(7) 0.0233(2) Uani 1 1 d . . . . .
N3 N 0.25476(11) 0.41796(6) 0.31891(7) 0.0213(2) Uani 1 1 d . . . . .
C3 C 0.15323(14) 0.66597(8) -0.17794(9) 0.0294(3) Uani 1 1 d . . . . .
H3A H 0.147710 0.689031 -0.245503 0.035 Uiso 1 1 calc R U . . .
N4 N 0.16547(11) 0.61637(6) 0.20893(7) 0.0242(2) Uani 1 1 d . . . . .
C4 C 0.15462(14) 0.57830(8) -0.16339(9) 0.0291(3) Uani 1 1 d . . . . .
H4A H 0.149574 0.541267 -0.221192 0.035 Uiso 1 1 calc R U . . .
C5 C 0.16339(13) 0.54445(7) -0.06437(9) 0.0249(2) Uani 1 1 d . . . . .
H5A H 0.163650 0.484378 -0.055339 0.030 Uiso 1 1 calc R U . . .
N5 N 0.18613(12) 0.57457(6) 0.30206(7) 0.0249(2) Uani 1 1 d . . . . .
C6 C 0.17180(12) 0.59755(7) 0.02192(8) 0.0206(2) Uani 1 1 d . . . . .
C7 C 0.18429(12) 0.56416(7) 0.12745(8) 0.0204(2) Uani 1 1 d . . . . .
C8 C 0.21925(12) 0.48200(7) 0.16823(8) 0.0198(2) Uani 1 1 d . . . . .
C9 C 0.21938(12) 0.49484(7) 0.27403(8) 0.0205(2) Uani 1 1 d . . . . .
C10 C 0.28734(13) 0.39935(7) 0.42611(8) 0.0211(2) Uani 1 1 d . . . . .
C11 C 0.16327(13) 0.39546(7) 0.49190(8) 0.0215(2) Uani 1 1 d . . . . .
C12 C 0.19780(14) 0.38432(7) 0.59661(8) 0.0243(2) Uani 1 1 d . . . . .
H12A H 0.115795 0.382197 0.643349 0.029 Uiso 1 1 calc R U . . .
C13 C 0.35040(15) 0.37625(7) 0.63413(9) 0.0273(3) Uani 1 1 d . . . . .
C14 C 0.46988(14) 0.37832(7) 0.56512(10) 0.0290(3) Uani 1 1 d . . . . .
H14A H 0.573534 0.371358 0.590411 0.035 Uiso 1 1 calc R U . . .
C15 C 0.44180(13) 0.39030(7) 0.46006(9) 0.0262(3) Uani 1 1 d . . . . .
C16 C -0.00117(13) 0.40169(8) 0.45089(9) 0.0263(3) Uani 1 1 d . . . . .
H16A H -0.071365 0.403523 0.508446 0.040 Uiso 1 1 calc R U . . .
H16B H -0.025585 0.351918 0.407806 0.040 Uiso 1 1 calc R U . . .
H16C H -0.013694 0.453683 0.409706 0.040 Uiso 1 1 calc R U . . .
C17 C 0.38564(18) 0.36585(9) 0.74818(10) 0.0383(3) Uani 1 1 d . . . . .
H17A H 0.489400 0.341546 0.758855 0.057 Uiso 1 1 calc R U . . .
H17B H 0.309120 0.327675 0.777637 0.057 Uiso 1 1 calc R U . . .
H17C H 0.381233 0.421590 0.781935 0.057 Uiso 1 1 calc R U . . .
C18 C 0.57315(14) 0.39349(9) 0.38685(11) 0.0367(3) Uani 1 1 d . . . . .
H18A H 0.669825 0.406635 0.425154 0.055 Uiso 1 1 calc R U . . .
H18B H 0.552346 0.437773 0.335063 0.055 Uiso 1 1 calc R U . . .
H18C H 0.582663 0.338152 0.352726 0.055 Uiso 1 1 calc R U . . .
C19 C 0.27377(14) 0.34530(7) 0.06427(9) 0.0269(3) Uani 1 1 d . . . . .
H19A H 0.192036 0.359078 0.011700 0.032 Uiso 1 1 calc R U . . .
H19B H 0.264768 0.284136 0.081748 0.032 Uiso 1 1 calc R U . . .
C20 C 0.43099(16) 0.36222(10) 0.02109(10) 0.0393(3) Uani 1 1 d . . . . .
H20A H 0.446999 0.324108 -0.037291 0.059 Uiso 1 1 calc R U . . .
H20B H 0.511525 0.351945 0.074524 0.059 Uiso 1 1 calc R U . . .
H20C H 0.436369 0.421566 -0.001976 0.059 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'
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 112.11(9) . . ?
N2 N1 C19 116.55(9) . . ?
C8 N1 C19 131.22(9) . . ?
C2 C1 C6 120.98(11) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C1 C2 C3 120.26(11) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
N1 N2 N3 105.82(8) . . ?
N2 N3 C9 110.62(9) . . ?
N2 N3 C10 120.45(9) . . ?
C9 N3 C10 128.56(9) . . ?
C4 C3 C2 119.55(11) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C7 N4 N5 112.52(9) . . ?
C3 C4 C5 120.25(11) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.99(11) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C9 N5 N4 103.15(9) . . ?
C5 C6 C1 117.96(10) . . ?
C5 C6 C7 122.51(10) . . ?
C1 C6 C7 119.52(10) . . ?
N4 C7 C8 106.64(9) . . ?
N4 C7 C6 120.56(9) . . ?
C8 C7 C6 132.77(10) . . ?
N1 C8 C9 104.78(9) . . ?
N1 C8 C7 151.90(10) . . ?
C9 C8 C7 103.32(9) . . ?
N5 C9 N3 138.99(10) . . ?
N5 C9 C8 114.36(9) . . ?
N3 C9 C8 106.65(9) . . ?
C11 C10 C15 123.15(10) . . ?
C11 C10 N3 118.21(9) . . ?
C15 C10 N3 118.56(10) . . ?
C12 C11 C10 117.44(10) . . ?
C12 C11 C16 121.48(10) . . ?
C10 C11 C16 121.08(10) . . ?
C11 C12 C13 121.36(11) . . ?
C11 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C14 C13 C12 119.04(11) . . ?
C14 C13 C17 120.40(11) . . ?
C12 C13 C17 120.56(12) . . ?
C13 C14 C15 121.86(11) . . ?
C13 C14 H14A 119.1 . . ?
C15 C14 H14A 119.1 . . ?
C14 C15 C10 117.12(11) . . ?
C14 C15 C18 120.98(11) . . ?
C10 C15 C18 121.90(11) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 110.59(10) . . ?
N1 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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
N1 N2 1.3325(13) . ?
N1 C8 1.3706(14) . ?
N1 C19 1.4701(14) . ?
C1 C2 1.3885(16) . ?
C1 C6 1.4050(15) . ?
C1 H1A 0.9500 . ?
C2 C3 1.3893(17) . ?
C2 H2A 0.9500 . ?
N2 N3 1.3415(13) . ?
N3 C9 1.3702(14) . ?
N3 C10 1.4427(14) . ?
C3 C4 1.3887(18) . ?
C3 H3A 0.9500 . ?
N4 C7 1.3538(14) . ?
N4 N5 1.3836(13) . ?
C4 C5 1.3927(16) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3976(15) . ?
C5 H5A 0.9500 . ?
N5 C9 1.3370(14) . ?
C6 C7 1.4696(15) . ?
C7 C8 1.4226(15) . ?
C8 C9 1.3907(15) . ?
C10 C11 1.3960(16) . ?
C10 C15 1.3990(15) . ?
C11 C12 1.3951(15) . ?
C11 C16 1.5040(15) . ?
C12 C13 1.3964(17) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3916(19) . ?
C13 C17 1.5128(16) . ?
C14 C15 1.3923(17) . ?
C14 H14A 0.9500 . ?
C15 C18 1.5074(17) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.5116(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C6 C1 C2 C3 -0.41(18) . . . . ?
C8 N1 N2 N3 0.59(12) . . . . ?
C19 N1 N2 N3 177.10(9) . . . . ?
N1 N2 N3 C9 0.29(12) . . . . ?
N1 N2 N3 C10 -173.30(9) . . . . ?
C1 C2 C3 C4 0.66(18) . . . . ?
C2 C3 C4 C5 -0.28(18) . . . . ?
C3 C4 C5 C6 -0.36(18) . . . . ?
C7 N4 N5 C9 0.42(12) . . . . ?
C4 C5 C6 C1 0.61(16) . . . . ?
C4 C5 C6 C7 -178.76(10) . . . . ?
C2 C1 C6 C5 -0.22(17) . . . . ?
C2 C1 C6 C7 179.16(10) . . . . ?
N5 N4 C7 C8 0.21(12) . . . . ?
N5 N4 C7 C6 -178.05(9) . . . . ?
C5 C6 C7 N4 -168.59(10) . . . . ?
C1 C6 C7 N4 12.06(15) . . . . ?
C5 C6 C7 C8 13.68(18) . . . . ?
C1 C6 C7 C8 -165.67(11) . . . . ?
N2 N1 C8 C9 -1.20(12) . . . . ?
C19 N1 C8 C9 -177.05(11) . . . . ?
N2 N1 C8 C7 179.72(18) . . . . ?
C19 N1 C8 C7 3.9(3) . . . . ?
N4 C7 C8 N1 178.36(18) . . . . ?
C6 C7 C8 N1 -3.7(3) . . . . ?
N4 C7 C8 C9 -0.73(11) . . . . ?
C6 C7 C8 C9 177.23(11) . . . . ?
N4 N5 C9 N3 179.37(13) . . . . ?
N4 N5 C9 C8 -0.94(12) . . . . ?
N2 N3 C9 N5 178.68(13) . . . . ?
C10 N3 C9 N5 -8.4(2) . . . . ?
N2 N3 C9 C8 -1.03(12) . . . . ?
C10 N3 C9 C8 171.91(10) . . . . ?
N1 C8 C9 N5 -178.48(9) . . . . ?
C7 C8 C9 N5 1.07(12) . . . . ?
N1 C8 C9 N3 1.30(11) . . . . ?
C7 C8 C9 N3 -179.14(9) . . . . ?
N2 N3 C10 C11 -111.08(11) . . . . ?
C9 N3 C10 C11 76.59(14) . . . . ?
N2 N3 C10 C15 72.06(13) . . . . ?
C9 N3 C10 C15 -100.27(13) . . . . ?
C15 C10 C11 C12 1.82(16) . . . . ?
N3 C10 C11 C12 -174.89(9) . . . . ?
C15 C10 C11 C16 -177.25(10) . . . . ?
N3 C10 C11 C16 6.04(15) . . . . ?
C10 C11 C12 C13 -0.83(16) . . . . ?
C16 C11 C12 C13 178.24(10) . . . . ?
C11 C12 C13 C14 -0.82(17) . . . . ?
C11 C12 C13 C17 178.87(11) . . . . ?
C12 C13 C14 C15 1.60(17) . . . . ?
C17 C13 C14 C15 -178.08(11) . . . . ?
C13 C14 C15 C10 -0.67(17) . . . . ?
C13 C14 C15 C18 179.18(11) . . . . ?
C11 C10 C15 C14 -1.09(17) . . . . ?
N3 C10 C15 C14 175.61(10) . . . . ?
C11 C10 C15 C18 179.06(11) . . . . ?
N3 C10 C15 C18 -4.25(16) . . . . ?
N2 N1 C19 C20 -99.97(12) . . . . ?
C8 N1 C19 C20 75.74(14) . . . . ?
