#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:17:55 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267021 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/83/7128342.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_7128342
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            'C25 H25 N3'
_chemical_formula_weight         367.48
_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                 95.571(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9028(7)
_cell_length_b                   12.5696(8)
_cell_length_c                   20.7598(18)
_cell_measurement_reflns_used    51730
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.159
_cell_measurement_theta_min      1.971
_cell_volume                     2052.4(3)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_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  0.0548
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            51730
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.159
_diffrn_reflns_theta_min         1.971
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6116
_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            block
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       'dark green'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.7019
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0698P)²+0.3432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3740
_reflns_number_total             4987
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02245h2.cif
_cod_data_source_block           wl451
_cod_depositor_comments
'Adding full bibliography for 7128333--7128355.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128342
_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 0.03986(13) 0.37621(8) 0.41697(5) 0.0274(2) Uani 1 1 d . . . . .
C1 C 0.43703(17) 0.34685(10) 0.28757(6) 0.0269(3) Uani 1 1 d . . . . .
H1A H 0.373179 0.285078 0.295692 0.032 Uiso 1 1 calc R U . . .
N2 N 0.04590(14) 0.29459(9) 0.46057(5) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.58641(17) 0.33593(10) 0.25827(6) 0.0297(3) Uani 1 1 d . . . . .
H2A H 0.624443 0.266956 0.247747 0.036 Uiso 1 1 calc R U . . .
C3 C 0.68083(17) 0.42408(11) 0.24415(7) 0.0318(3) Uani 1 1 d . . . . .
H3A H 0.783390 0.416249 0.224243 0.038 Uiso 1 1 calc R U . . .
N3 N 0.19864(13) 0.25398(8) 0.45634(5) 0.0262(2) Uani 1 1 d . . . . .
C4 C 0.62278(16) 0.52419(11) 0.25964(7) 0.0303(3) Uani 1 1 d . . . . .
H4A H 0.684956 0.585627 0.249470 0.036 Uiso 1 1 calc R U . . .
C5 C 0.47548(16) 0.53522(10) 0.28969(6) 0.0265(3) Uani 1 1 d . . . . .
H5A H 0.438916 0.604628 0.300010 0.032 Uiso 1 1 calc R U . . .
C6 C 0.37738(16) 0.44709(9) 0.30562(6) 0.0234(3) Uani 1 1 d . . . . .
C7 C 0.22539(16) 0.46265(10) 0.33975(6) 0.0254(3) Uani 1 1 d . . . . .
C8 C 0.13557(15) 0.56577(9) 0.33115(6) 0.0246(3) Uani 1 1 d . . . . .
C9 C 0.08343(16) 0.60447(10) 0.26897(6) 0.0267(3) Uani 1 1 d . . . . .
H9A H 0.102588 0.562466 0.232330 0.032 Uiso 1 1 calc R U . . .
C10 C 0.00477(16) 0.70237(10) 0.25978(7) 0.0305(3) Uani 1 1 d . . . . .
H10A H -0.028075 0.726938 0.217120 0.037 Uiso 1 1 calc R U . . .
C11 C -0.02648(17) 0.76489(10) 0.31235(7) 0.0337(3) Uani 1 1 d . . . . .
H11A H -0.082835 0.831367 0.306033 0.040 Uiso 1 1 calc R U . . .
C12 C 0.02545(18) 0.72919(11) 0.37405(7) 0.0339(3) Uani 1 1 d . . . . .
H12A H 0.005845 0.771803 0.410386 0.041 Uiso 1 1 calc R U . . .
C13 C 0.10617(17) 0.63140(10) 0.38336(7) 0.0302(3) Uani 1 1 d . . . . .
H13A H 0.142204 0.608600 0.426127 0.036 Uiso 1 1 calc R U . . .
C14 C 0.18855(16) 0.38825(10) 0.38639(6) 0.0253(3) Uani 1 1 d . . . . .
C15 C 0.28922(16) 0.30415(10) 0.41460(6) 0.0276(3) Uani 1 1 d . . . . .
H15A H 0.401316 0.286541 0.405449 0.033 Uiso 1 1 calc R U . . .
C16 C 0.24758(16) 0.16038(10) 0.49418(6) 0.0252(3) Uani 1 1 d . . . . .
C17 C 0.20216(17) 0.06142(10) 0.46764(6) 0.0273(3) Uani 1 1 d . . . . .
C18 C 0.24368(17) -0.02757(10) 0.50558(6) 0.0297(3) Uani 1 1 d . . . . .
H18A H 0.214610 -0.096146 0.488730 0.036 Uiso 1 1 calc R U . . .
C19 C 0.32656(17) -0.01898(11) 0.56747(7) 0.0302(3) Uani 1 1 d . . . . .
C20 C 0.37314(17) 0.08094(11) 0.59107(7) 0.0326(3) Uani 1 1 d . . . . .
H20A H 0.431972 0.086950 0.633042 0.039 Uiso 1 1 calc R U . . .
C21 C 0.33614(17) 0.17286(11) 0.55498(7) 0.0301(3) Uani 1 1 d . . . . .
C22 C 0.1133(2) 0.05038(12) 0.40039(7) 0.0374(3) Uani 1 1 d . . . . .
H22A H 0.021369 0.102816 0.394145 0.056 Uiso 1 1 calc R U . . .
H22B H 0.065777 -0.021421 0.394792 0.056 Uiso 1 1 calc R U . . .
H22C H 0.194861 0.062561 0.368498 0.056 Uiso 1 1 calc R U . . .
C23 C 0.3642(2) -0.11642(12) 0.60874(8) 0.0420(4) Uani 1 1 d . . . . .
H23A H 0.329212 -0.180180 0.583737 0.063 Uiso 1 1 calc R U . . .
H23B H 0.301440 -0.112456 0.647135 0.063 Uiso 1 1 calc R U . . .
H23C H 0.486418 -0.119959 0.622188 0.063 Uiso 1 1 calc R U . . .
C24 C 0.3906(2) 0.28019(12) 0.58177(8) 0.0434(4) Uani 1 1 d . . . . .
H24A H 0.328886 0.336064 0.556311 0.065 Uiso 1 1 calc R U . . .
H24B H 0.513053 0.289169 0.579473 0.065 Uiso 1 1 calc R U . . .
H24C H 0.365310 0.285178 0.626960 0.065 Uiso 1 1 calc R U . . .
C25 C -0.12029(17) 0.43278(12) 0.40625(7) 0.0361(3) Uani 1 1 d . . . . .
H25A H -0.144162 0.448811 0.360061 0.054 Uiso 1 1 calc R U . . .
H25B H -0.113222 0.499281 0.431000 0.054 Uiso 1 1 calc R U . . .
H25C H -0.211731 0.388469 0.420432 0.054 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 C14 113.93(10) . . ?
N2 N1 C25 116.35(10) . . ?
C14 N1 C25 129.59(11) . . ?
C2 C1 C6 121.77(11) . . ?
C2 C1 H1A 119.1 . . ?
C6 C1 H1A 119.1 . . ?
N3 N2 N1 102.68(9) . . ?
C3 C2 C1 120.90(12) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C2 C3 C4 118.69(12) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
N2 N3 C15 114.31(10) . . ?
N2 N3 C16 118.43(10) . . ?
C15 N3 C16 127.23(11) . . ?
C5 C4 C3 120.54(12) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 122.29(12) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C1 C6 C5 115.76(11) . . ?
C1 C6 C7 123.99(11) . . ?
C5 C6 C7 120.24(11) . . ?
C14 C7 C6 118.78(11) . . ?
C14 C7 C8 122.68(11) . . ?
C6 C7 C8 117.67(10) . . ?
C13 C8 C9 116.87(11) . . ?
C13 C8 C7 122.45(12) . . ?
C9 C8 C7 120.60(11) . . ?
C10 C9 C8 121.53(12) . . ?
C10 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C9 C10 C11 120.51(12) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C12 C11 C10 119.09(12) . . ?
C12 C11 H11A 120.5 . . ?
C10 C11 H11A 120.5 . . ?
C11 C12 C13 120.48(13) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C8 121.49(13) . . ?
C12 C13 H13A 119.3 . . ?
C8 C13 H13A 119.3 . . ?
N1 C14 C7 128.95(11) . . ?
N1 C14 C15 101.24(10) . . ?
C7 C14 C15 129.80(12) . . ?
N3 C15 C14 107.83(11) . . ?
N3 C15 H15A 126.1 . . ?
C14 C15 H15A 126.1 . . ?
C21 C16 C17 123.16(11) . . ?
C21 C16 N3 119.04(11) . . ?
C17 C16 N3 117.80(11) . . ?
C18 C17 C16 117.21(12) . . ?
C18 C17 C22 120.95(12) . . ?
C16 C17 C22 121.84(12) . . ?
C19 C18 C17 121.76(12) . . ?
C19 C18 H18A 119.1 . . ?
C17 C18 H18A 119.1 . . ?
C20 C19 C18 118.89(12) . . ?
C20 C19 C23 120.31(13) . . ?
C18 C19 C23 120.80(13) . . ?
C19 C20 C21 121.83(12) . . ?
C19 C20 H20A 119.1 . . ?
C21 C20 H20A 119.1 . . ?
C16 C21 C20 117.09(12) . . ?
C16 C21 C24 122.45(12) . . ?
C20 C21 C24 120.46(12) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 1.3658(14) . ?
N1 C14 1.3969(16) . ?
N1 C25 1.4499(17) . ?
C1 C2 1.3863(19) . ?
C1 C6 1.4087(16) . ?
C1 H1A 0.9500 . ?
N2 N3 1.3213(15) . ?
C2 C3 1.3830(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3877(19) . ?
C3 H3A 0.9500 . ?
N3 C15 1.3347(16) . ?
N3 C16 1.4463(15) . ?
C4 C5 1.3801(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4096(17) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4658(18) . ?
C7 C14 1.3970(18) . ?
C7 C8 1.4802(17) . ?
C8 C13 1.3993(18) . ?
C8 C9 1.4035(18) . ?
C9 C10 1.3834(18) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3896(19) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.4152(17) . ?
C15 H15A 0.9500 . ?
C16 C21 1.3914(18) . ?
C16 C17 1.3932(18) . ?
C17 C18 1.3889(18) . ?
C17 C22 1.5072(19) . ?
C18 C19 1.389(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3849(19) . ?
C19 C23 1.5077(18) . ?
C20 C21 1.3926(19) . ?
C20 H20A 0.9500 . ?
C21 C24 1.5060(19) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C14 N1 N2 N3 -1.12(14) . . . . ?
C25 N1 N2 N3 175.28(11) . . . . ?
C6 C1 C2 C3 -1.6(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
N1 N2 N3 C15 0.93(14) . . . . ?
N1 N2 N3 C16 -176.87(10) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C2 C1 C6 C5 2.39(18) . . . . ?
C2 C1 C6 C7 -176.63(12) . . . . ?
C4 C5 C6 C1 -1.41(18) . . . . ?
C4 C5 C6 C7 177.66(12) . . . . ?
C1 C6 C7 C14 36.27(18) . . . . ?
C5 C6 C7 C14 -142.72(12) . . . . ?
C1 C6 C7 C8 -154.08(12) . . . . ?
C5 C6 C7 C8 26.94(17) . . . . ?
C14 C7 C8 C13 46.01(18) . . . . ?
C6 C7 C8 C13 -123.22(13) . . . . ?
C14 C7 C8 C9 -137.29(13) . . . . ?
C6 C7 C8 C9 53.48(16) . . . . ?
C13 C8 C9 C10 -0.77(18) . . . . ?
C7 C8 C9 C10 -177.65(12) . . . . ?
C8 C9 C10 C11 -0.69(19) . . . . ?
C9 C10 C11 C12 1.45(19) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C8 -0.8(2) . . . . ?
C9 C8 C13 C12 1.49(19) . . . . ?
C7 C8 C13 C12 178.31(12) . . . . ?
N2 N1 C14 C7 179.95(12) . . . . ?
C25 N1 C14 C7 4.1(2) . . . . ?
N2 N1 C14 C15 0.87(14) . . . . ?
C25 N1 C14 C15 -174.93(13) . . . . ?
C6 C7 C14 N1 -168.31(12) . . . . ?
C8 C7 C14 N1 22.6(2) . . . . ?
C6 C7 C14 C15 10.5(2) . . . . ?
C8 C7 C14 C15 -158.60(13) . . . . ?
N2 N3 C15 C14 -0.43(15) . . . . ?
C16 N3 C15 C14 177.13(11) . . . . ?
N1 C14 C15 N3 -0.26(13) . . . . ?
C7 C14 C15 N3 -179.33(13) . . . . ?
N2 N3 C16 C21 -93.53(15) . . . . ?
C15 N3 C16 C21 88.99(16) . . . . ?
N2 N3 C16 C17 86.11(15) . . . . ?
C15 N3 C16 C17 -91.37(16) . . . . ?
C21 C16 C17 C18 2.24(19) . . . . ?
N3 C16 C17 C18 -177.38(11) . . . . ?
C21 C16 C17 C22 -177.14(12) . . . . ?
N3 C16 C17 C22 3.23(18) . . . . ?
C16 C17 C18 C19 0.18(19) . . . . ?
C22 C17 C18 C19 179.57(12) . . . . ?
C17 C18 C19 C20 -1.9(2) . . . . ?
C17 C18 C19 C23 177.58(12) . . . . ?
C18 C19 C20 C21 1.3(2) . . . . ?
C23 C19 C20 C21 -178.17(13) . . . . ?
C17 C16 C21 C20 -2.8(2) . . . . ?
N3 C16 C21 C20 176.83(11) . . . . ?
C17 C16 C21 C24 177.39(13) . . . . ?
N3 C16 C21 C24 -3.0(2) . . . . ?
C19 C20 C21 C16 0.9(2) . . . . ?
C19 C20 C21 C24 -179.23(13) . . . . ?
