#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:17:55 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267021 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/83/7128348.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_7128348
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 H21 N5'
_chemical_formula_weight         283.38
_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                 97.239(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.043(4)
_cell_length_b                   16.924(5)
_cell_length_c                   7.147(2)
_cell_measurement_reflns_used    21722
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      3.323
_cell_measurement_theta_min      3.323
_cell_volume                     1565.1(8)
_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 0.993
_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  0.0662
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21722
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         3.323
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6844
_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            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       rod
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.024(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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0609
_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)+(0.0775P)²+0.5226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2228
_reflns_number_total             3569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02245h2.cif
_cod_data_source_block           wl487a
_cod_depositor_comments
'Adding full bibliography for 7128333--7128355.cif.'
_cod_original_cell_volume        1564.9(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128348
_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 0.51788(13) 0.85415(9) 0.4856(2) 0.0362(4) Uani 1 1 d . . . . .
C1 C 0.39645(18) 0.57666(12) 0.3765(3) 0.0446(6) Uani 1 1 d . . . . .
H1A H 0.453277 0.544471 0.425338 0.054 Uiso 1 1 calc R U . . .
N2 N 0.59743(14) 0.89597(11) 0.5682(2) 0.0431(5) Uani 1 1 d . . . . .
C2 C 0.30571(19) 0.54128(13) 0.2989(3) 0.0484(6) Uani 1 1 d . . . . .
H2A H 0.300583 0.485286 0.296094 0.058 Uiso 1 1 calc R U . . .
N3 N 0.66760(13) 0.84308(11) 0.6415(2) 0.0421(5) Uani 1 1 d . . . . .
C3 C 0.22257(19) 0.58641(13) 0.2254(3) 0.0504(6) Uani 1 1 d . . . . .
H3A H 0.159971 0.561978 0.172504 0.060 Uiso 1 1 calc R U . . .
N4 N 0.58183(13) 0.64941(10) 0.5575(2) 0.0408(5) Uani 1 1 d . . . . .
C4 C 0.23137(18) 0.66802(14) 0.2296(4) 0.0554(6) Uani 1 1 d . . . . .
H4A H 0.174732 0.699725 0.177590 0.066 Uiso 1 1 calc R U . . .
N5 N 0.66458(13) 0.69339(11) 0.6398(2) 0.0435(5) Uani 1 1 d . . . . .
C5 C 0.32193(17) 0.70361(13) 0.3088(3) 0.0464(6) Uani 1 1 d . . . . .
H5A H 0.326291 0.759643 0.311154 0.056 Uiso 1 1 calc R U . . .
C6 C 0.40671(15) 0.65935(11) 0.3850(2) 0.0348(5) Uani 1 1 d . . . . .
C7 C 0.50285(15) 0.69511(12) 0.4755(2) 0.0344(5) Uani 1 1 d . . . . .
C8 C 0.53507(15) 0.77474(11) 0.5044(2) 0.0336(5) Uani 1 1 d . . . . .
C9 C 0.63258(16) 0.76798(12) 0.6051(3) 0.0374(5) Uani 1 1 d . . . . .
C10 C 0.76400(18) 0.86971(16) 0.7533(3) 0.0544(6) Uani 1 1 d . . . . .
H10A H 0.767734 0.847439 0.882045 0.065 Uiso 1 1 calc R U . A 1
H10B H 0.762775 0.928010 0.764133 0.065 Uiso 1 1 calc R U . A 1
C12 C 0.8723(2) 0.8759(2) 0.4854(4) 0.0801(10) Uani 1 1 d . . . . .
H12A H 0.815915 0.852242 0.397430 0.096 Uiso 1 1 calc R U . B 1
H12B H 0.856351 0.933007 0.490124 0.096 Uiso 1 1 calc R U . B 1
C13 C 0.9612(2) 0.8711(2) 0.3909(5) 0.0940(12) Uani 1 1 d . . . . .
H13A H 1.019159 0.888578 0.484557 0.113 Uiso 1 1 calc R U . C 1
H13B H 0.972074 0.813865 0.372055 0.113 Uiso 1 1 calc R U . C 1
C15 C 1.0802(3) 0.8860(2) 0.1420(6) 0.1080(13) Uani 1 1 d . . . . .
H15A H 1.082730 0.914795 0.023654 0.162 Uiso 1 1 calc R U . D 1
H15B H 1.139378 0.901243 0.233143 0.162 Uiso 1 1 calc R U . D 1
H15C H 1.082679 0.829069 0.118149 0.162 Uiso 1 1 calc R U . D 1
C16 C 0.42911(17) 0.89804(12) 0.3931(3) 0.0420(5) Uani 1 1 d . . . . .
H16A H 0.414204 0.880849 0.261504 0.063 Uiso 1 1 calc R U . . .
H16B H 0.444814 0.954684 0.396999 0.063 Uiso 1 1 calc R U . . .
H16C H 0.368793 0.888001 0.458665 0.063 Uiso 1 1 calc R U . . .
C11 C 0.8574(3) 0.8458(3) 0.6692(5) 0.0590(12) Uani 0.684(5) 1 d . . P E 1
H11A H 0.918442 0.861331 0.758297 0.071 Uiso 0.684(5) 1 calc R U P E 1
H11B H 0.857596 0.787378 0.661746 0.071 Uiso 0.684(5) 1 calc R U P E 1
C14 C 0.9787(3) 0.9065(3) 0.2224(6) 0.0714(14) Uani 0.684(5) 1 d . . P E 1
H14A H 0.976770 0.964427 0.240245 0.086 Uiso 0.684(5) 1 calc R U P E 1
H14B H 0.920321 0.892570 0.125757 0.086 Uiso 0.684(5) 1 calc R U P E 1
C11A C 0.8373(5) 0.9071(5) 0.6314(9) 0.043(2) Uani 0.316(5) 1 d . . P E 2
H11C H 0.804200 0.957385 0.585863 0.051 Uiso 0.316(5) 1 calc R U P E 2
H11D H 0.899285 0.921978 0.718836 0.051 Uiso 0.316(5) 1 calc R U P E 2
C14A C 1.0102(7) 0.8454(5) 0.2491(12) 0.060(2) Uani 0.316(5) 1 d . . P E 2
H14C H 0.954618 0.825481 0.153587 0.072 Uiso 0.316(5) 1 calc R U P E 2
H14D H 1.048773 0.798067 0.299835 0.072 Uiso 0.316(5) 1 calc R U P E 2
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 111.74(16) . . ?
N2 N1 C16 117.34(16) . . ?
C8 N1 C16 130.92(17) . . ?
C2 C1 C6 121.4(2) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
N1 N2 N3 105.92(16) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
N2 N3 C9 110.63(17) . . ?
N2 N3 C10 120.17(18) . . ?
C9 N3 C10 129.11(19) . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C7 N4 N5 112.71(17) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C9 N5 N4 102.71(16) . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C1 116.94(19) . . ?
C5 C6 C7 122.99(18) . . ?
C1 C6 C7 120.06(18) . . ?
N4 C7 C8 106.43(17) . . ?
N4 C7 C6 120.94(18) . . ?
C8 C7 C6 132.60(18) . . ?
N1 C8 C9 105.12(17) . . ?
N1 C8 C7 151.39(19) . . ?
C9 C8 C7 103.47(17) . . ?
N5 C9 N3 138.7(2) . . ?
N5 C9 C8 114.67(18) . . ?
N3 C9 C8 106.59(18) . . ?
N3 C10 C11 112.7(2) . . ?
N3 C10 C11A 112.0(3) . . ?
N3 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N3 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11A C12 C13 142.8(4) . . ?
C13 C12 C11 128.7(3) . . ?
C13 C12 H12A 105.1 . . ?
C11 C12 H12A 105.1 . . ?
C13 C12 H12B 105.1 . . ?
C11 C12 H12B 105.1 . . ?
H12A C12 H12B 105.9 . . ?
C14A C13 C12 151.5(5) . . ?
C14 C13 C12 128.5(4) . . ?
C14 C13 H13A 105.2 . . ?
C12 C13 H13A 105.2 . . ?
C14 C13 H13B 105.2 . . ?
C12 C13 H13B 105.2 . . ?
H13A C13 H13B 105.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11A 107.6 . . ?
C10 C11 H11A 107.6 . . ?
C12 C11 H11B 107.6 . . ?
C10 C11 H11B 107.6 . . ?
H11A C11 H11B 107.0 . . ?
C13 C14 C15 117.9(4) . . ?
C13 C14 H14A 107.8 . . ?
C15 C14 H14A 107.8 . . ?
C13 C14 H14B 107.8 . . ?
C15 C14 H14B 107.8 . . ?
H14A C14 H14B 107.2 . . ?
C12 C11A C10 127.1(6) . . ?
C12 C11A H11C 105.5 . . ?
C10 C11A H11C 105.5 . . ?
C12 C11A H11D 105.5 . . ?
C10 C11A H11D 105.5 . . ?
H11C C11A H11D 106.1 . . ?
C13 C14A C15 130.1(7) . . ?
C13 C14A H14C 104.7 . . ?
C15 C14A H14C 104.7 . . ?
C13 C14A H14D 104.7 . . ?
C15 C14A H14D 104.7 . . ?
H14C C14A H14D 105.7 . . ?
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 1.331(2) . ?
N1 C8 1.366(2) . ?
N1 C16 1.462(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.406(3) . ?
C1 H1A 0.9500 . ?
N2 N3 1.339(2) . ?
C2 C3 1.375(3) . ?
C2 H2A 0.9500 . ?
N3 C9 1.364(3) . ?
N3 C10 1.473(3) . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9500 . ?
N4 C7 1.360(2) . ?
N4 N5 1.380(2) . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9500 . ?
N5 C9 1.343(3) . ?
C5 C6 1.389(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.467(3) . ?
C7 C8 1.419(3) . ?
C8 C9 1.385(3) . ?
C10 C11 1.481(5) . ?
C10 C11A 1.511(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C11A 1.302(7) . ?
C12 C13 1.416(4) . ?
C12 C11 1.444(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14A 1.337(8) . ?
C13 C14 1.389(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 C14A 1.438(8) . ?
C15 C14 1.547(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
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 0.1(2) . . . . ?
C16 N1 N2 N3 179.98(15) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
N1 N2 N3 C9 0.1(2) . . . . ?
N1 N2 N3 C10 -176.60(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C7 N4 N5 C9 0.2(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C7 177.51(18) . . . . ?
N5 N4 C7 C8 0.2(2) . . . . ?
N5 N4 C7 C6 -178.27(15) . . . . ?
C5 C6 C7 N4 176.31(18) . . . . ?
C1 C6 C7 N4 -2.2(3) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
C1 C6 C7 C8 179.85(19) . . . . ?
N2 N1 C8 C9 -0.3(2) . . . . ?
C16 N1 C8 C9 179.88(18) . . . . ?
N2 N1 C8 C7 177.9(3) . . . . ?
C16 N1 C8 C7 -1.9(5) . . . . ?
N4 C7 C8 N1 -178.7(3) . . . . ?
C6 C7 C8 N1 -0.5(5) . . . . ?
N4 C7 C8 C9 -0.48(19) . . . . ?
C6 C7 C8 C9 177.71(19) . . . . ?
N4 N5 C9 N3 178.6(2) . . . . ?
N4 N5 C9 C8 -0.6(2) . . . . ?
N2 N3 C9 N5 -179.5(2) . . . . ?
C10 N3 C9 N5 -3.2(4) . . . . ?
N2 N3 C9 C8 -0.3(2) . . . . ?
C10 N3 C9 C8 176.03(18) . . . . ?
N1 C8 C9 N5 179.77(15) . . . . ?
C7 C8 C9 N5 0.7(2) . . . . ?
N1 C8 C9 N3 0.3(2) . . . . ?
C7 C8 C9 N3 -178.75(15) . . . . ?
N2 N3 C10 C11 -119.0(3) . . . . ?
C9 N3 C10 C11 65.0(3) . . . . ?
N2 N3 C10 C11A -72.4(4) . . . . ?
C9 N3 C10 C11A 111.6(4) . . . . ?
C11A C12 C13 C14A -178.5(11) . . . . ?
C11 C12 C13 C14 -173.2(4) . . . . ?
C13 C12 C11 C10 169.6(3) . . . . ?
N3 C10 C11 C12 62.8(4) . . . . ?
C12 C13 C14 C15 -175.3(4) . . . . ?
C13 C12 C11A C10 -143.2(6) . . . . ?
N3 C10 C11A C12 -55.1(8) . . . . ?
C12 C13 C14A C15 138.4(9) . . . . ?
