#------------------------------------------------------------------------------
#$Date: 2020-05-13 02:14:59 +0300 (Wed, 13 May 2020) $
#$Revision: 251986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038341.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_4038341
loop_
_publ_author_name
'Tsyrenova, Biligma'
'Khrustalev, Victor N.'
'Nenajdenko, Valentine Georgievich'
_publ_section_title
;
 2H-bis-1,2,3-triazolo-isoquinoline. Design, synthesis and photophysical
 study.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00263
_journal_year                    2020
_chemical_formula_moiety         'C23 H16 N6 O'
_chemical_formula_sum            'C23 H16 N6 O'
_chemical_formula_weight         392.42
_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
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                112.346(3)
_cell_angle_beta                 101.577(3)
_cell_angle_gamma                106.514(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4118(12)
_cell_length_b                   10.1482(14)
_cell_length_c                   11.4542(15)
_cell_measurement_reflns_used    3403
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.54
_cell_measurement_theta_min      3.16
_cell_volume                     909.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15676
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.717
_diffrn_reflns_theta_min         2.619
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         6510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0792
_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)+(0.085P)²+0.9346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1899
_refine_ls_wR_factor_ref         0.2167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4381
_reflns_number_total             6510
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00263_si_002.cif
_cod_data_source_block           Bil405
_cod_database_code               4038341
_shelx_shelxl_version_number     2018/3
_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   0.982
_shelx_estimated_absorpt_t_max   0.986
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
O1 O 0.9785(2) 0.95972(19) 1.33216(15) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.9238(2) 0.5936(2) 0.83408(19) 0.0188(4) Uani 1 1 d . . . . .
N2 N 0.8740(2) 0.4622(2) 0.72355(19) 0.0181(4) Uani 1 1 d . . . . .
N3 N 0.7208(2) 0.4283(2) 0.66129(17) 0.0151(3) Uani 1 1 d . . . . .
N4 N 0.6460(2) 0.1756(2) 0.47076(18) 0.0154(3) Uani 1 1 d . . . . .
N5 N 0.5018(2) 0.0822(2) 0.37516(17) 0.0148(3) Uani 1 1 d . . . . .
N6 N 0.3877(2) 0.1353(2) 0.38444(18) 0.0149(3) Uani 1 1 d . . . . .
C1 C 0.8049(2) 0.6442(2) 0.8433(2) 0.0153(4) Uani 1 1 d . . . . .
C2 C 0.6701(2) 0.5383(2) 0.7316(2) 0.0141(4) Uani 1 1 d . . . . .
C3 C 0.5053(2) 0.5156(2) 0.6832(2) 0.0148(4) Uani 1 1 d . . . . .
C4 C 0.4439(3) 0.6165(3) 0.7568(2) 0.0182(4) Uani 1 1 d . . . . .
H4 H 0.511850 0.704859 0.840171 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2863(3) 0.5891(3) 0.7099(2) 0.0211(4) Uani 1 1 d . . . . .
H5 H 0.247008 0.658744 0.761252 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1837(3) 0.4602(3) 0.5876(2) 0.0198(4) Uani 1 1 d . . . . .
H6 H 0.075534 0.443065 0.555518 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2400(3) 0.3582(3) 0.5138(2) 0.0173(4) Uani 1 1 d . . . . .
H7 H 0.170573 0.270333 0.430575 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3991(2) 0.3836(2) 0.5610(2) 0.0137(4) Uani 1 1 d . . . . .
C9 C 0.4615(2) 0.2742(2) 0.4939(2) 0.0140(4) Uani 1 1 d . . . . .
C10 C 0.6185(2) 0.2955(2) 0.5445(2) 0.0141(4) Uani 1 1 d . . . . .
C11 C 0.4708(2) -0.0687(2) 0.2750(2) 0.0142(4) Uani 1 1 d . . . . .
C12 C 0.5878(3) -0.1258(2) 0.2825(2) 0.0168(4) Uani 1 1 d . . . . .
H12 H 0.688019 -0.065153 0.352523 0.020 Uiso 1 1 calc R U . . .
C13 C 0.5544(3) -0.2748(2) 0.1845(2) 0.0183(4) Uani 1 1 d . . . . .
H13 H 0.633042 -0.316248 0.187577 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4078(3) -0.3635(3) 0.0826(2) 0.0191(4) Uani 1 1 d . . . . .
H14 H 0.386113 -0.465064 0.016454 0.023 Uiso 1 1 calc R U . . .
C15 C 0.2931(3) -0.3029(3) 0.0777(2) 0.0188(4) Uani 1 1 d . . . . .
H15 H 0.192834 -0.363395 0.007812 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3236(3) -0.1550(2) 0.1740(2) 0.0159(4) Uani 1 1 d . . . . .
H16 H 0.245106 -0.113535 0.170740 0.019 Uiso 1 1 calc R U . . .
C17 C 0.8320(3) 0.7871(2) 0.9621(2) 0.0156(4) Uani 1 1 d . . . . .
C18 C 0.8992(2) 0.8038(2) 1.0897(2) 0.0153(4) Uani 1 1 d . . . . .
H18 H 0.929693 0.725660 1.098943 0.018 Uiso 1 1 calc R U . . .
C19 C 0.9214(2) 0.9352(2) 1.2031(2) 0.0160(4) Uani 1 1 d . . . . .
C20 C 0.8791(3) 1.0511(3) 1.1900(2) 0.0195(4) Uani 1 1 d . . . . .
H20 H 0.893162 1.140476 1.267684 0.023 Uiso 1 1 calc R U . . .
C21 C 0.8163(3) 1.0352(3) 1.0627(2) 0.0193(4) Uani 1 1 d . . . . .
H21 H 0.789381 1.115037 1.053530 0.023 Uiso 1 1 calc R U . . .
C22 C 0.7923(3) 0.9036(2) 0.9484(2) 0.0183(4) Uani 1 1 d . . . . .
H22 H 0.749092 0.893325 0.861408 0.022 Uiso 1 1 calc R U . . .
C23 C 1.0257(3) 0.8459(3) 1.3523(2) 0.0221(4) Uani 1 1 d . . . . .
H23A H 1.056483 0.873433 1.448167 0.033 Uiso 1 1 calc R U . . .
H23B H 1.115597 0.842271 1.322370 0.033 Uiso 1 1 calc R U . . .
H23C H 0.937302 0.743970 1.300277 0.033 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'
O O 0.0106 0.0060 '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
C19 O1 C23 117.80(17) . . ?
N2 N1 C1 110.38(18) . . ?
N1 N2 N3 105.84(17) . . ?
N2 N3 C2 112.56(17) . . ?
N2 N3 C10 125.87(18) . . ?
C2 N3 C10 121.47(18) . . ?
C10 N4 N5 101.08(17) . . ?
N6 N5 N4 116.47(17) . . ?
N6 N5 C11 121.81(17) . . ?
N4 N5 C11 121.61(17) . . ?
N5 N6 C9 103.32(17) . . ?
N1 C1 C2 108.73(18) . . ?
N1 C1 C17 120.00(19) . . ?
C2 C1 C17 131.23(19) . . ?
N3 C2 C1 102.50(17) . . ?
N3 C2 C3 119.91(18) . . ?
C1 C2 C3 137.45(19) . . ?
C4 C3 C8 117.64(19) . . ?
C4 C3 C2 122.38(19) . . ?
C8 C3 C2 119.90(18) . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 120.87(19) . . ?
C7 C8 C9 122.42(19) . . ?
C3 C8 C9 116.60(18) . . ?
N6 C9 C10 107.38(18) . . ?
N6 C9 C8 129.91(19) . . ?
C10 C9 C8 122.54(19) . . ?
N4 C10 N3 128.72(19) . . ?
N4 C10 C9 111.74(18) . . ?
N3 C10 C9 119.49(18) . . ?
C12 C11 C16 122.03(19) . . ?
C12 C11 N5 119.02(18) . . ?
C16 C11 N5 118.94(18) . . ?
C11 C12 C13 118.2(2) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 118.8(2) . . ?
C15 C16 H16 120.6 . . ?
C11 C16 H16 120.6 . . ?
C22 C17 C18 120.32(19) . . ?
C22 C17 C1 121.15(19) . . ?
C18 C17 C1 118.52(19) . . ?
C19 C18 C17 119.57(19) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
O1 C19 C18 124.4(2) . . ?
O1 C19 C20 115.15(19) . . ?
C18 C19 C20 120.37(19) . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 119.5(2) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C19 1.364(3) . ?
O1 C23 1.427(3) . ?
N1 N2 1.313(2) . ?
N1 C1 1.364(3) . ?
N2 N3 1.351(2) . ?
N3 C2 1.376(3) . ?
N3 C10 1.381(3) . ?
N4 C10 1.321(3) . ?
N4 N5 1.350(2) . ?
N5 N6 1.336(2) . ?
N5 C11 1.422(2) . ?
N6 C9 1.338(3) . ?
C1 C2 1.389(3) . ?
C1 C17 1.473(3) . ?
C2 C3 1.456(3) . ?
C3 C4 1.404(3) . ?
C3 C8 1.416(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.440(3) . ?
C9 C10 1.394(3) . ?
C11 C12 1.385(3) . ?
C11 C16 1.387(3) . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.389(3) . ?
C17 C18 1.395(3) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(3) . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 N1 N2 N3 0.0(2) . . . . ?
N1 N2 N3 C2 0.0(2) . . . . ?
N1 N2 N3 C10 -176.3(2) . . . . ?
C10 N4 N5 N6 0.0(2) . . . . ?
C10 N4 N5 C11 -176.19(19) . . . . ?
N4 N5 N6 C9 0.1(2) . . . . ?
C11 N5 N6 C9 176.29(18) . . . . ?
N2 N1 C1 C2 0.1(3) . . . . ?
N2 N1 C1 C17 177.73(19) . . . . ?
N2 N3 C2 C1 0.0(2) . . . . ?
C10 N3 C2 C1 176.48(19) . . . . ?
N2 N3 C2 C3 -176.31(18) . . . . ?
C10 N3 C2 C3 0.1(3) . . . . ?
N1 C1 C2 N3 -0.1(2) . . . . ?
C17 C1 C2 N3 -177.4(2) . . . . ?
N1 C1 C2 C3 175.3(2) . . . . ?
C17 C1 C2 C3 -2.1(4) . . . . ?
N3 C2 C3 C4 174.1(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
N3 C2 C3 C8 -2.6(3) . . . . ?
C1 C2 C3 C8 -177.3(2) . . . . ?
C8 C3 C4 C5 -1.4(3) . . . . ?
C2 C3 C4 C5 -178.1(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C3 -1.5(3) . . . . ?
C6 C7 C8 C9 174.7(2) . . . . ?
C4 C3 C8 C7 2.1(3) . . . . ?
C2 C3 C8 C7 179.0(2) . . . . ?
C4 C3 C8 C9 -174.22(19) . . . . ?
C2 C3 C8 C9 2.6(3) . . . . ?
N5 N6 C9 C10 -0.2(2) . . . . ?
N5 N6 C9 C8 -175.5(2) . . . . ?
C7 C8 C9 N6 -2.0(4) . . . . ?
C3 C8 C9 N6 174.2(2) . . . . ?
C7 C8 C9 C10 -176.7(2) . . . . ?
C3 C8 C9 C10 -0.4(3) . . . . ?
N5 N4 C10 N3 177.5(2) . . . . ?
N5 N4 C10 C9 -0.1(2) . . . . ?
N2 N3 C10 N4 0.6(4) . . . . ?
C2 N3 C10 N4 -175.3(2) . . . . ?
N2 N3 C10 C9 178.1(2) . . . . ?
C2 N3 C10 C9 2.1(3) . . . . ?
N6 C9 C10 N4 0.2(2) . . . . ?
C8 C9 C10 N4 175.88(19) . . . . ?
N6 C9 C10 N3 -177.70(18) . . . . ?
C8 C9 C10 N3 -2.0(3) . . . . ?
N6 N5 C11 C12 -170.58(19) . . . . ?
N4 N5 C11 C12 5.4(3) . . . . ?
N6 N5 C11 C16 8.5(3) . . . . ?
N4 N5 C11 C16 -175.56(19) . . . . ?
C16 C11 C12 C13 0.1(3) . . . . ?
N5 C11 C12 C13 179.11(19) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
N5 C11 C16 C15 -179.05(19) . . . . ?
N1 C1 C17 C22 130.1(2) . . . . ?
C2 C1 C17 C22 -52.9(3) . . . . ?
N1 C1 C17 C18 -49.7(3) . . . . ?
C2 C1 C17 C18 127.4(3) . . . . ?
C22 C17 C18 C19 2.2(3) . . . . ?
C1 C17 C18 C19 -178.0(2) . . . . ?
C23 O1 C19 C18 3.1(3) . . . . ?
C23 O1 C19 C20 -179.3(2) . . . . ?
C17 C18 C19 O1 176.5(2) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
O1 C19 C20 C21 -178.5(2) . . . . ?
C18 C19 C20 C21 -0.7(3) . . . . ?
C19 C20 C21 C22 1.3(4) . . . . ?
C20 C21 C22 C17 -0.1(4) . . . . ?
C18 C17 C22 C21 -1.7(3) . . . . ?
C1 C17 C22 C21 178.6(2) . . . . ?
