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#$Date: 2021-07-04 04:37:43 +0300 (Sun, 04 Jul 2021) $
#$Revision: 266964 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/87/4518796.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_4518796
loop_
_publ_author_name
'Ibrahim, Hamada Mohamed'
'Behbehani, Haider'
_publ_section_title
;
 TFA-catalyzed Q-Tube Reactor-Assisted Strategy for the Synthesis of
 Pyrido[1,2-b][1,2,4]triazine and
 Pyrido[1',2':2,3][1,2,4]triazino[5,6-b]indole Derivatives.
;
_journal_issue                   24
_journal_name_full               'ACS omega'
_journal_page_first              16086
_journal_page_last               16099
_journal_paper_doi               10.1021/acsomega.1c01980
_journal_volume                  6
_journal_year                    2021
_chemical_formula_sum            'C20 H12 N6'
_chemical_formula_weight         336.36
_chemical_name_common            Hamada_GH68C_11_10_17
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 91.551(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4315(3)
_cell_length_b                   15.4721(7)
_cell_length_c                   13.5859(6)
_cell_measurement_reflns_used    9749
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      66.1456
_cell_measurement_theta_min      4.3317
_cell_volume                     1561.55(12)
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14333
_diffrn_reflns_theta_full        66.49
_diffrn_reflns_theta_max         66.49
_diffrn_reflns_theta_min         5.72
_diffrn_source_type              'Incoatec Cu-ImS'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0416P)²+0.5934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                2311
_reflns_number_total             2641
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao1c01980_si_006.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4518794--4518800.cif.'
_cod_database_code               4518796
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N4 0.6370(2) 0.63789(11) 0.55329(12) 0.0543(4) Uani d . 1 . .
N N2 0.7851(2) 0.48844(9) 0.45868(11) 0.0468(4) Uani d . 1 . .
C C8 0.8434(2) 0.57651(11) 0.31846(13) 0.0429(4) Uani d . 1 . .
C C12 0.7760(2) 0.56518(11) 0.41564(13) 0.0434(4) Uani d . 1 . .
N N3 0.7065(2) 0.63806(10) 0.46010(11) 0.0491(4) Uani d . 1 . .
N N5 0.7184(2) 0.41726(11) 0.60917(11) 0.0542(4) Uani d . 1 . .
N N6 1.1951(3) 0.71957(13) -0.08698(14) 0.0741(6) Uani d . 1 . .
H H6A 1.2517 0.7675 -0.0941 0.089 Uiso calc R 1 . .
H H6B 1.1965 0.6811 -0.1326 0.089 Uiso calc R 1 . .
C C3 1.1022(3) 0.70438(13) -0.00255(14) 0.0551(5) Uani d . 1 . .
C C4 1.0984(3) 0.76581(13) 0.07202(15) 0.0595(5) Uani d . 1 . .
H H4 1.1566 0.8184 0.064 0.071 Uiso calc R 1 . .
C C5 1.0098(3) 0.74964(12) 0.15704(14) 0.0563(5) Uani d . 1 . .
H H5 1.0066 0.7925 0.2049 0.068 Uiso calc R 1 . .
C C6 0.9240(3) 0.67098(11) 0.17454(13) 0.0484(4) Uani d . 1 . .
C C9 0.8454(2) 0.65557(11) 0.27078(14) 0.0476(4) Uani d . 1 . .
C C13 0.6465(2) 0.56321(13) 0.59592(14) 0.0488(4) Uani d . 1 . .
C C15 0.5928(2) 0.53610(14) 0.69246(14) 0.0535(5) Uani d . 1 . .
C C16 0.5142(3) 0.57636(17) 0.77154(16) 0.0668(6) Uani d . 1 . .
H H16 0.479 0.634 0.7678 0.08 Uiso calc R 1 . .
C C17 0.4893(3) 0.5289(2) 0.85591(17) 0.0773(7) Uani d . 1 . .
H H17 0.4381 0.5547 0.9102 0.093 Uiso calc R 1 . .
C C18 0.5406(3) 0.4424(2) 0.86021(16) 0.0777(7) Uani d . 1 . .
H H18 0.5236 0.4116 0.918 0.093 Uiso calc R 1 . .
C C20 0.6422(2) 0.44808(14) 0.69643(14) 0.0540(5) Uani d . 1 . .
C C14 0.7224(2) 0.48518(12) 0.55068(13) 0.0470(4) Uani d . 1 . .
C C2 1.0090(3) 0.62690(12) 0.01123(14) 0.0575(5) Uani d . 1 . .
H H2 1.0047 0.5859 -0.0388 0.069 Uiso calc R 1 . .
C C1 0.9242(3) 0.61068(12) 0.09758(14) 0.0529(5) Uani d . 1 . .
H H1 0.8651 0.5582 0.1053 0.063 Uiso calc R 1 . .
C C10 0.7705(3) 0.72624(13) 0.32339(16) 0.0589(5) Uani d . 1 . .
H H10 0.7682 0.7807 0.2944 0.071 Uiso calc R 1 . .
C C11 0.7036(3) 0.71640(13) 0.41310(16) 0.0599(5) Uani d . 1 . .
H H11 0.6539 0.7639 0.4443 0.072 Uiso calc R 1 . .
C C7 0.9182(3) 0.49993(11) 0.27613(13) 0.0463(4) Uani d . 1 . .
N N1 0.9761(3) 0.43916(10) 0.24133(12) 0.0598(5) Uani d . 1 . .
C C19 0.6157(3) 0.40095(17) 0.78148(15) 0.0671(6) Uani d . 1 . .
H H19 0.6477 0.3429 0.7854 0.08 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 N4 N3 . . 113.26(15) ?
C12 N2 C14 . . 115.38(15) ?
C9 C8 C12 . . 123.13(16) ?
C9 C8 C7 . . 122.20(16) ?
C12 C8 C7 . . 114.59(15) ?
N2 C12 N3 . . 123.52(16) ?
N2 C12 C8 . . 120.04(15) ?
N3 C12 C8 . . 116.43(16) ?
C11 N3 N4 . . 115.32(15) ?
C11 N3 C12 . . 121.21(16) ?
N4 N3 C12 . . 123.47(15) ?
C14 N5 C20 . . 104.67(16) ?
C3 N6 H6A . . 120.0 ?
C3 N6 H6B . . 120.0 ?
H6A N6 H6B . . 120.0 ?
N6 C3 C4 . . 120.80(19) ?
N6 C3 C2 . . 121.29(19) ?
C4 C3 C2 . . 117.91(19) ?
C5 C4 C3 . . 120.69(19) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 122.35(18) ?
C4 C5 H5 . . 118.8 ?
C6 C5 H5 . . 118.8 ?
C5 C6 C1 . . 116.31(18) ?
C5 C6 C9 . . 119.23(17) ?
C1 C6 C9 . . 124.44(17) ?
C8 C9 C10 . . 115.68(17) ?
C8 C9 C6 . . 124.78(16) ?
C10 C9 C6 . . 119.49(17) ?
N4 C13 C15 . . 130.77(18) ?
N4 C13 C14 . . 124.19(17) ?
C15 C13 C14 . . 105.03(17) ?
C16 C15 C20 . . 121.3(2) ?
C16 C15 C13 . . 135.0(2) ?
C20 C15 C13 . . 103.71(16) ?
C15 C16 C17 . . 118.3(2) ?
C15 C16 H16 . . 120.8 ?
C17 C16 H16 . . 120.8 ?
C16 C17 C18 . . 120.3(2) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C19 C18 C17 . . 122.1(2) ?
C19 C18 H18 . . 119.0 ?
C17 C18 H18 . . 119.0 ?
C19 C20 N5 . . 126.3(2) ?
C19 C20 C15 . . 119.83(19) ?
N5 C20 C15 . . 113.83(17) ?
N5 C14 N2 . . 127.12(17) ?
N5 C14 C13 . . 112.72(16) ?
N2 C14 C13 . . 120.16(17) ?
C1 C2 C3 . . 120.82(18) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C2 C1 C6 . . 121.78(18) ?
C2 C1 H1 . . 119.1 ?
C6 C1 H1 . . 119.1 ?
C11 C10 C9 . . 121.92(19) ?
C11 C10 H10 . . 119.0 ?
C9 C10 H10 . . 119.0 ?
C10 C11 N3 . . 121.60(18) ?
C10 C11 H11 . . 119.2 ?
N3 C11 H11 . . 119.2 ?
N1 C7 C8 . . 179.0(2) ?
C20 C19 C18 . . 118.2(2) ?
C20 C19 H19 . . 120.9 ?
C18 C19 H19 . . 120.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N4 C13 . 1.294(3) ?
N4 N3 . 1.380(2) ?
N2 C12 . 1.324(2) ?
N2 C14 . 1.347(2) ?
C8 C9 . 1.384(2) ?
C8 C12 . 1.435(2) ?
C8 C7 . 1.435(2) ?
C12 N3 . 1.386(2) ?
N3 C11 . 1.370(3) ?
N5 C14 . 1.318(2) ?
N5 C20 . 1.411(2) ?
N6 C3 . 1.375(3) ?
N6 H6A . 0.86 ?
N6 H6B . 0.86 ?
C3 C4 . 1.390(3) ?
C3 C2 . 1.400(3) ?
C4 C5 . 1.368(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.397(3) ?
C5 H5 . 0.93 ?
C6 C1 . 1.401(3) ?
C6 C9 . 1.466(3) ?
C9 C10 . 1.427(3) ?
C13 C15 . 1.444(3) ?
C13 C14 . 1.474(3) ?
C15 C16 . 1.385(3) ?
C15 C20 . 1.411(3) ?
C16 C17 . 1.378(3) ?
C16 H16 . 0.93 ?
C17 C18 . 1.392(4) ?
C17 H17 . 0.93 ?
C18 C19 . 1.378(3) ?
C18 H18 . 0.93 ?
C20 C19 . 1.385(3) ?
C2 C1 . 1.370(3) ?
C2 H2 . 0.93 ?
C1 H1 . 0.93 ?
C10 C11 . 1.337(3) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C7 N1 . 1.142(2) ?
C19 H19 . 0.93 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C14 N2 C12 N3 . . . . -0.4(2) ?
C14 N2 C12 C8 . . . . 178.38(15) ?
C9 C8 C12 N2 . . . . -177.13(16) ?
C7 C8 C12 N2 . . . . -0.3(2) ?
C9 C8 C12 N3 . . . . 1.7(2) ?
C7 C8 C12 N3 . . . . 178.54(15) ?
C13 N4 N3 C11 . . . . -178.32(17) ?
C13 N4 N3 C12 . . . . 1.4(2) ?
N2 C12 N3 C11 . . . . 178.61(18) ?
C8 C12 N3 C11 . . . . -0.2(2) ?
N2 C12 N3 N4 . . . . -1.0(3) ?
C8 C12 N3 N4 . . . . -179.86(15) ?
N6 C3 C4 C5 . . . . -178.3(2) ?
C2 C3 C4 C5 . . . . 1.6(3) ?
C3 C4 C5 C6 . . . . 1.8(3) ?
C4 C5 C6 C1 . . . . -3.6(3) ?
C4 C5 C6 C9 . . . . 174.73(19) ?
C12 C8 C9 C10 . . . . -1.7(3) ?
C7 C8 C9 C10 . . . . -178.31(17) ?
C12 C8 C9 C6 . . . . 175.63(16) ?
C7 C8 C9 C6 . . . . -0.9(3) ?
C5 C6 C9 C8 . . . . -144.19(19) ?
C1 C6 C9 C8 . . . . 34.0(3) ?
C5 C6 C9 C10 . . . . 33.1(3) ?
C1 C6 C9 C10 . . . . -148.7(2) ?
N3 N4 C13 C15 . . . . 178.84(17) ?
N3 N4 C13 C14 . . . . -0.4(3) ?
N4 C13 C15 C16 . . . . 0.5(4) ?
C14 C13 C15 C16 . . . . 179.9(2) ?
N4 C13 C15 C20 . . . . -178.48(19) ?
C14 C13 C15 C20 . . . . 0.84(18) ?
C20 C15 C16 C17 . . . . 1.7(3) ?
C13 C15 C16 C17 . . . . -177.2(2) ?
C15 C16 C17 C18 . . . . -0.7(3) ?
C16 C17 C18 C19 . . . . -0.5(4) ?
C14 N5 C20 C19 . . . . -177.65(19) ?
C14 N5 C20 C15 . . . . 1.6(2) ?
C16 C15 C20 C19 . . . . -1.4(3) ?
C13 C15 C20 C19 . . . . 177.76(17) ?
C16 C15 C20 N5 . . . . 179.28(17) ?
C13 C15 C20 N5 . . . . -1.5(2) ?
C20 N5 C14 N2 . . . . 179.53(17) ?
C20 N5 C14 C13 . . . . -1.0(2) ?
C12 N2 C14 N5 . . . . -179.21(17) ?
C12 N2 C14 C13 . . . . 1.3(2) ?
N4 C13 C14 N5 . . . . 179.46(17) ?
C15 C13 C14 N5 . . . . 0.1(2) ?
N4 C13 C14 N2 . . . . -1.0(3) ?
C15 C13 C14 N2 . . . . 179.62(15) ?
N6 C3 C2 C1 . . . . 176.8(2) ?
C4 C3 C2 C1 . . . . -3.1(3) ?
C3 C2 C1 C6 . . . . 1.2(3) ?
C5 C6 C1 C2 . . . . 2.1(3) ?
C9 C6 C1 C2 . . . . -176.14(18) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
C6 C9 C10 C11 . . . . -177.27(19) ?
C9 C10 C11 N3 . . . . 1.2(3) ?
N4 N3 C11 C10 . . . . 178.45(19) ?
C12 N3 C11 C10 . . . . -1.2(3) ?
C9 C8 C7 N1 . . . . -58.(13) ?
C12 C8 C7 N1 . . . . 126.(13) ?
N5 C20 C19 C18 . . . . 179.33(19) ?
C15 C20 C19 C18 . . . . 0.1(3) ?
C17 C18 C19 C20 . . . . 0.8(3) ?
