#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/30/7213029.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213029
loop_
_publ_author_name
'Crabb, Derek L.'
'McCullough, Kevin J.'
'Preston, Peter N.'
'Rosair, Georgina M.'
'Bishop, Brian C.'
'Wright, Stanley H. B.'
'Clegg, William'
'Coles, Simon'
_publ_section_title
;
 Preparation of [1,2,4]triazoloquinazolinium betaines and molecular
 rearrangements of putative [1,2,4]triazolo[4,3-a][1,3,5]triazinium
 betaines
;
_journal_issue                   11
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1517
_journal_paper_doi               10.1039/a900941h
_journal_year                    1999
_chemical_formula_sum            'C17 H15 N5'
_chemical_formula_weight         289.34
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 101.377(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7511(7)
_cell_length_b                   7.3223(12)
_cell_length_c                   20.122(5)
_cell_measurement_temperature    140(2)
_cell_volume                     1408.5(4)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5617
_diffrn_reflns_theta_max         24.85
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.976
_refine_ls_goodness_of_fit_obs   1.077
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.223
_refine_ls_restrained_S_obs      1.077
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_obs          0.0437
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0598P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1333
_refine_ls_wR_factor_obs         0.1031
_reflns_number_observed          1661
_reflns_number_total             2100
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            900941hsup1.cif
_cod_data_source_block           compound8a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7213029
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.3161(2) 0.2277(2) 0.87847(7) 0.0237(4) Uani 1 d .
N2 N 0.42370(14) 0.2886(2) 0.99601(7) 0.0201(4) Uani 1 d .
N3 N 0.20715(15) 0.3630(2) 0.96291(7) 0.0238(4) Uani 1 d .
N4 N 0.2378(2) 0.4081(2) 1.03105(8) 0.0247(4) Uani 1 d .
N5 N 0.4604(2) 0.3729(2) 1.11154(8) 0.0243(4) Uani 1 d .
C1 C 0.4343(2) 0.1542(2) 0.86944(9) 0.0220(4) Uani 1 d .
C2 C 0.3158(2) 0.2916(2) 0.94176(9) 0.0210(4) Uani 1 d .
C3 C 0.5532(2) 0.2152(2) 0.98837(9) 0.0199(4) Uani 1 d .
C4 C 0.6695(2) 0.2083(2) 1.04111(9) 0.0229(4) Uani 1 d .
H4 H 0.6653(2) 0.2550(2) 1.08471(9) 0.028 Uiso 1 calc R
C5 C 0.7917(2) 0.1314(2) 1.02825(10) 0.0263(5) Uani 1 d .
H5 H 0.8720(2) 0.1261(2) 1.06363(10) 0.032 Uiso 1 calc R
C6 C 0.7991(2) 0.0621(2) 0.96482(9) 0.0267(5) Uani 1 d .
H6 H 0.8839(2) 0.0098(2) 0.95728(9) 0.032 Uiso 1 calc R
C7 C 0.6835(2) 0.0690(2) 0.91271(10) 0.0251(5) Uani 1 d .
H7 H 0.6890(2) 0.0210(2) 0.86945(10) 0.030 Uiso 1 calc R
C8 C 0.5579(2) 0.1466(2) 0.92329(9) 0.0208(4) Uani 1 d .
C9 C 0.3737(2) 0.3625(2) 1.05269(9) 0.0208(4) Uani 1 d .
C10 C 0.2975(2) 0.5377(2) 1.17387(10) 0.0247(5) Uani 1 d .
H10 H 0.2243(2) 0.5453(2) 1.13509(10) 0.030 Uiso 1 calc R
C11 C 0.2802(2) 0.6154(2) 1.23492(10) 0.0284(5) Uani 1 d .
H11 H 0.1953(2) 0.6770(2) 1.23688(10) 0.034 Uiso 1 calc R
C12 C 0.3835(2) 0.6048(2) 1.29266(10) 0.0302(5) Uani 1 d .
H12 H 0.3706(2) 0.6591(2) 1.33385(10) 0.036 Uiso 1 calc R
C13 C 0.5069(2) 0.5132(3) 1.28930(10) 0.0305(5) Uani 1 d .
H13 H 0.5785(2) 0.5026(3) 1.32865(10) 0.037 Uiso 1 calc R
C14 C 0.5254(2) 0.4374(2) 1.22874(9) 0.0271(5) Uani 1 d .
H14 H 0.6106(2) 0.3759(2) 1.22735(9) 0.032 Uiso 1 calc R
C15 C 0.4229(2) 0.4483(2) 1.16941(9) 0.0218(4) Uani 1 d .
C16 C 0.0694(2) 0.3981(3) 0.92252(10) 0.0317(5) Uani 1 d G
H161 H 0.0650(16) 0.3527(15) 0.8779(3) 0.038 Uiso 1 d G
H162 H 0.0510(15) 0.5256(4) 0.9206(7) 0.038 Uiso 1 d G
H163 H 0.0015(12) 0.3377(15) 0.9426(7) 0.038 Uiso 1 d G
C17 C 0.4370(2) 0.0737(3) 0.80176(10) 0.0298(5) Uani 1 d G
H171 H 0.4614(12) -0.0513(5) 0.8088(7) 0.036 Uiso 1 d G
H172 H 0.3478(7) 0.0834(17) 0.7724(6) 0.036 Uiso 1 d G
H173 H 0.5056(10) 0.1320(16) 0.7810(7) 0.036 Uiso 1 d G
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
C1 N1 C2 115.7(2)
C2 N2 C3 119.16(15)
C2 N2 C9 107.62(14)
C3 N2 C9 133.19(15)
C2 N3 N4 112.47(15)
C2 N3 C16 127.0(2)
N4 N3 C16 120.5(2)
C9 N4 N3 105.44(14)
C9 N5 C15 123.0(2)
N1 C1 C8 122.1(2)
N1 C1 C17 117.5(2)
C8 C1 C17 120.3(2)
N3 C2 N1 126.0(2)
N3 C2 N2 106.9(2)
N1 C2 N2 127.1(2)
C4 C3 N2 122.9(2)
C4 C3 C8 121.5(2)
N2 C3 C8 115.5(2)
C5 C4 C3 118.2(2)
C4 C5 C6 121.5(2)
C7 C6 C5 120.1(2)
C6 C7 C8 120.4(2)
C7 C8 C3 118.3(2)
C7 C8 C1 121.5(2)
C3 C8 C1 120.3(2)
N5 C9 N4 133.7(2)
N5 C9 N2 118.7(2)
N4 C9 N2 107.61(15)
C11 C10 C15 120.3(2)
C12 C11 C10 121.5(2)
C11 C12 C13 118.7(2)
C14 C13 C12 120.1(2)
C13 C14 C15 122.2(2)
C14 C15 N5 115.3(2)
C14 C15 C10 117.1(2)
N5 C15 C10 127.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.316(2)
N1 C2 1.357(2)
N2 C2 1.358(2)
N2 C3 1.408(2)
N2 C9 1.432(2)
N3 C2 1.325(2)
N3 N4 1.384(2)
N3 C16 1.449(2)
N4 C9 1.353(2)
N5 C9 1.314(2)
N5 C15 1.401(2)
C1 C8 1.454(2)
C1 C17 1.489(3)
C3 C4 1.393(3)
C3 C8 1.412(3)
C4 C5 1.387(2)
C5 C6 1.389(3)
C6 C7 1.381(3)
C7 C8 1.405(2)
C10 C11 1.394(3)
C10 C15 1.405(3)
C11 C12 1.382(3)
C12 C13 1.390(3)
C13 C14 1.383(3)
C14 C15 1.400(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 852668
