#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:17:55 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267021 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/83/7128341.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_7128341
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            'C17 H15 Cl2 N5'
_chemical_formula_weight         360.24
_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                102.837(12)
_cell_angle_beta                 102.334(13)
_cell_angle_gamma                99.423(14)
_cell_formula_units_Z            2
_cell_length_a                   6.907(3)
_cell_length_b                   10.401(4)
_cell_length_c                   12.709(4)
_cell_measurement_reflns_used    26608
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.437
_cell_measurement_theta_min      3.122
_cell_volume                     848.0(6)
_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 0.994
_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  0.0620
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26608
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         3.122
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_T_max  0.7382
_exptl_absorpt_correction_T_min  0.6908
_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    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0452
_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)+(0.0298P)²+0.2421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2807
_reflns_number_total             3838
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02245h2.cif
_cod_data_source_block           wl475
_cod_depositor_comments
'Adding full bibliography for 7128333--7128355.cif.'
_cod_original_cell_volume        848.0(5)
_cod_database_code               7128341
_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   0.892
_shelx_estimated_absorpt_t_max   0.962
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
Cl1 Cl 0.57164(12) 1.13981(6) 0.77553(5) 0.0597(2) Uani 1 1 d . . . . .
N1 N 0.2908(2) 0.41310(14) 0.60730(12) 0.0245(3) Uani 1 1 d . . . . .
Cl2 Cl 0.87358(9) 1.03755(6) 0.67010(5) 0.0531(2) Uani 1 1 d . . . . .
N2 N 0.3876(2) 0.46479(15) 0.71435(12) 0.0269(3) Uani 1 1 d . . . . .
N3 N 0.4553(2) 0.59749(14) 0.72798(12) 0.0242(3) Uani 1 1 d . . . . .
N4 N 0.3137(2) 0.68280(15) 0.47428(12) 0.0288(4) Uani 1 1 d . . . . .
N5 N 0.4175(2) 0.73679(15) 0.58590(12) 0.0279(3) Uani 1 1 d . . . . .
C8 C 0.0865(3) 0.5390(2) 0.25072(16) 0.0357(5) Uani 1 1 d . . . . .
H8 H 0.137693 0.633796 0.268090 0.043 Uiso 1 1 calc R U . . .
C9 C -0.0220(3) 0.4682(2) 0.14229(17) 0.0426(5) Uani 1 1 d . . . . .
H9 H -0.044683 0.515286 0.086353 0.051 Uiso 1 1 calc R U . . .
C10 C -0.0973(3) 0.3299(2) 0.11472(17) 0.0419(5) Uani 1 1 d . . . . .
H10 H -0.170813 0.281791 0.040384 0.050 Uiso 1 1 calc R U . . .
C11 C -0.0639(3) 0.2634(2) 0.19696(18) 0.0429(5) Uani 1 1 d . . . . .
H11 H -0.115353 0.168513 0.179239 0.051 Uiso 1 1 calc R U . . .
C12 C 0.0438(3) 0.3332(2) 0.30514(17) 0.0359(5) Uani 1 1 d . . . . .
H12 H 0.065514 0.285315 0.360576 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1208(3) 0.47192(18) 0.33436(14) 0.0261(4) Uani 1 1 d . . . . .
C14 C 0.2364(3) 0.54836(18) 0.44876(14) 0.0244(4) Uani 1 1 d . . . . .
C15 C 0.2923(2) 0.50962(17) 0.54971(14) 0.0228(4) Uani 1 1 d . . . . .
C16 C 0.3997(3) 0.62925(17) 0.62759(14) 0.0239(4) Uani 1 1 d . . . . .
C17 C 0.5600(3) 0.68365(18) 0.83625(14) 0.0269(4) Uani 1 1 d . . . . .
C18 C 0.6013(3) 0.6300(2) 0.92714(16) 0.0332(4) Uani 1 1 d . . . . .
H18 H 0.563757 0.535440 0.918149 0.040 Uiso 1 1 calc R U . . .
C19 C 0.6985(3) 0.7178(2) 1.03142(17) 0.0403(5) Uani 1 1 d . . . . .
H19 H 0.726585 0.683198 1.094873 0.048 Uiso 1 1 calc R U . . .
C20 C 0.7549(3) 0.8551(2) 1.04382(18) 0.0442(5) Uani 1 1 d . . . . .
H20 H 0.823287 0.914323 1.115435 0.053 Uiso 1 1 calc R U . . .
C21 C 0.7122(4) 0.9065(2) 0.95233(18) 0.0456(5) Uani 1 1 d . . . . .
H21 H 0.749850 1.001110 0.961332 0.055 Uiso 1 1 calc R U . . .
C22 C 0.6144(3) 0.82053(19) 0.84730(16) 0.0353(5) Uani 1 1 d . . . . .
H22 H 0.585335 0.855370 0.784033 0.042 Uiso 1 1 calc R U . . .
C23 C 0.2002(3) 0.26804(18) 0.57034(17) 0.0322(4) Uani 1 1 d . . . . .
H23A H 0.052189 0.253781 0.544558 0.048 Uiso 1 1 calc R U . . .
H23B H 0.234732 0.227815 0.632747 0.048 Uiso 1 1 calc R U . . .
H23C H 0.253076 0.225332 0.508930 0.048 Uiso 1 1 calc R U . . .
C24 C 0.6244(3) 1.0657(2) 0.64816(17) 0.0406(5) Uani 1 1 d . . . . .
H24A H 0.525595 0.978630 0.610807 0.049 Uiso 1 1 calc R U . . .
H24B H 0.608008 1.126064 0.598149 0.049 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'
Cl Cl 0.1484 0.1585 '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 C15 111.85(14) . . ?
N2 N1 C23 117.26(14) . . ?
C15 N1 C23 130.89(15) . . ?
N1 N2 N3 106.32(13) . . ?
N2 N3 C16 110.12(14) . . ?
N2 N3 C17 120.12(14) . . ?
C16 N3 C17 129.69(15) . . ?
C14 N4 N5 112.68(14) . . ?
C16 N5 N4 103.09(14) . . ?
C9 C8 C13 120.55(19) . . ?
C9 C8 H8 119.7 . . ?
C13 C8 H8 119.7 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 118.81(19) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 117.77(17) . . ?
C12 C13 C14 122.35(17) . . ?
C8 C13 C14 119.88(17) . . ?
N4 C14 C15 106.22(15) . . ?
N4 C14 C13 121.10(15) . . ?
C15 C14 C13 132.69(17) . . ?
N1 C15 C16 105.43(15) . . ?
N1 C15 C14 150.64(17) . . ?
C16 C15 C14 103.93(15) . . ?
N5 C16 N3 139.65(17) . . ?
N5 C16 C15 114.08(16) . . ?
N3 C16 C15 106.27(15) . . ?
C22 C17 C18 121.73(17) . . ?
C22 C17 N3 117.95(16) . . ?
C18 C17 N3 120.31(17) . . ?
C19 C18 C17 118.43(19) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C20 C19 C18 120.55(19) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.11(19) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 118.90(19) . . ?
C17 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Cl2 C24 Cl1 111.60(11) . . ?
Cl2 C24 H24A 109.3 . . ?
Cl1 C24 H24A 109.3 . . ?
Cl2 C24 H24B 109.3 . . ?
Cl1 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
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
Cl1 C24 1.771(2) . ?
N1 N2 1.325(2) . ?
N1 C15 1.368(2) . ?
N1 C23 1.462(2) . ?
Cl2 C24 1.767(2) . ?
N2 N3 1.342(2) . ?
N3 C16 1.380(2) . ?
N3 C17 1.426(2) . ?
N4 C14 1.351(2) . ?
N4 N5 1.386(2) . ?
N5 C16 1.339(2) . ?
C8 C9 1.389(3) . ?
C8 C13 1.396(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.472(2) . ?
C14 C15 1.423(2) . ?
C15 C16 1.384(2) . ?
C17 C22 1.379(3) . ?
C17 C18 1.387(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 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
C15 N1 N2 N3 -0.28(18) . . . . ?
C23 N1 N2 N3 -179.62(14) . . . . ?
N1 N2 N3 C16 -0.03(18) . . . . ?
N1 N2 N3 C17 177.47(14) . . . . ?
C14 N4 N5 C16 -0.15(19) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C11 C12 C13 C14 -179.78(18) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C9 C8 C13 C14 179.85(17) . . . . ?
N5 N4 C14 C15 -0.11(19) . . . . ?
N5 N4 C14 C13 179.99(15) . . . . ?
C12 C13 C14 N4 178.43(17) . . . . ?
C8 C13 C14 N4 -1.2(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C8 C13 C14 C15 178.97(18) . . . . ?
N2 N1 C15 C16 0.47(19) . . . . ?
C23 N1 C15 C16 179.68(17) . . . . ?
N2 N1 C15 C14 -178.8(3) . . . . ?
C23 N1 C15 C14 0.4(4) . . . . ?
N4 C14 C15 N1 179.6(3) . . . . ?
C13 C14 C15 N1 -0.6(4) . . . . ?
N4 C14 C15 C16 0.31(18) . . . . ?
C13 C14 C15 C16 -179.81(18) . . . . ?
N4 N5 C16 N3 -179.0(2) . . . . ?
N4 N5 C16 C15 0.4(2) . . . . ?
N2 N3 C16 N5 179.8(2) . . . . ?
C17 N3 C16 N5 2.6(4) . . . . ?
N2 N3 C16 C15 0.31(19) . . . . ?
C17 N3 C16 C15 -176.88(16) . . . . ?
N1 C15 C16 N5 179.94(14) . . . . ?
C14 C15 C16 N5 -0.4(2) . . . . ?
N1 C15 C16 N3 -0.45(18) . . . . ?
C14 C15 C16 N3 179.17(13) . . . . ?
N2 N3 C17 C22 -175.68(16) . . . . ?
C16 N3 C17 C22 1.3(3) . . . . ?
N2 N3 C17 C18 3.1(2) . . . . ?
C16 N3 C17 C18 -179.94(17) . . . . ?
C22 C17 C18 C19 0.5(3) . . . . ?
N3 C17 C18 C19 -178.29(17) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
C18 C17 C22 C21 -0.2(3) . . . . ?
N3 C17 C22 C21 178.53(18) . . . . ?
C20 C21 C22 C17 0.4(3) . . . . ?
