#------------------------------------------------------------------------------
#$Date: 2022-03-03 23:12:28 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273261 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519354.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_4519354
loop_
_publ_author_name
'Shafran, Yuri M.'
'Hussein, Aqeel A.'
'Beliaev, Nikolai A.'
'Shevyrin, Vadim A.'
'Shityakov, Sergey'
'Beryozkina, Tetyana V.'
'Bakulev, Vasiliy A.'
_publ_section_title
;
 Selective Synthesis of Azoloyl NH-1,2,3-Triazoles and Azolyl
 Diazoketones: Experimental and Computational Insights.
;
_journal_issue                   6
_journal_name_full               'ACS omega'
_journal_page_first              5008
_journal_page_last               5031
_journal_paper_doi               10.1021/acsomega.1c05898
_journal_volume                  7
_journal_year                    2022
_chemical_formula_moiety         'C10 H6 N6 O3'
_chemical_formula_sum            'C10 H6 N6 O3'
_chemical_formula_weight         258.21
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-06-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                91.354(10)
_cell_angle_beta                 92.008(9)
_cell_angle_gamma                92.293(12)
_cell_formula_units_Z            2
_cell_length_a                   5.6104(7)
_cell_length_b                   5.7380(10)
_cell_length_c                   17.8464(17)
_cell_measurement_reflns_used    753
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.3910
_cell_measurement_theta_min      3.8340
_cell_volume                     573.53(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -46.00 -21.00   1.00  100.00    --   21.89 -64.00 -60.00   25
  2  ω     55.00  89.00   1.00  100.00    --   21.89  64.00  76.00   34
  3  ω    -46.00   5.00   1.00  100.00    --  -23.61  64.00  76.00   51
  4  ω     18.00  44.00   1.00  100.00    --  -23.61  64.00  76.00   26
  5  ω     32.00  98.00   1.00  100.00    --   21.89-178.00 -30.00   66
  6  ω    -93.00   5.00   1.00  100.00    --  -23.61 -77.00-180.00   98
  7  ω   -100.00 -48.00   1.00  100.00    --  -23.61 178.00  30.00   52
  8  ω    -87.00  -3.00   1.00  100.00    --  -23.61 -64.00 -60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0142702000
_diffrn_orient_matrix_UB_12      -0.0845938000
_diffrn_orient_matrix_UB_13      -0.0289498000
_diffrn_orient_matrix_UB_21      0.1192436000
_diffrn_orient_matrix_UB_22      0.0423224000
_diffrn_orient_matrix_UB_23      -0.0040846000
_diffrn_orient_matrix_UB_31      0.0400923000
_diffrn_orient_matrix_UB_32      -0.0797947000
_diffrn_orient_matrix_UB_33      0.0269777000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5290
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         3.428
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1446
_refine_ls_R_factor_gt           0.0550
_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1214
_reflns_number_total             2804
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c05898_si_002.cif
_cod_data_source_block           exp_580
_cod_database_code               4519354
_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.
;
_reflns_odcompleteness_completeness 98.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.650
_oxdiff_exptl_absorpt_empirical_full_min 0.610
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 1.0788(4) 0.1585(4) 0.11736(11) 0.0804(7) Uani 1 1 d . . . . .
O2 O 1.2113(4) -0.1202(5) 0.04902(12) 0.0946(8) Uani 1 1 d . . . . .
O3 O 0.8560(4) 0.5404(4) 0.39918(11) 0.0780(7) Uani 1 1 d . . . . .
N1 N 0.9519(4) -0.0300(4) 0.25338(11) 0.0543(6) Uani 1 1 d . . . . .
N2 N 1.1944(4) -0.0227(5) 0.26253(12) 0.0663(7) Uani 1 1 d . . . . .
N3 N 1.2508(4) 0.1461(4) 0.31069(11) 0.0636(7) Uani 1 1 d . . . . .
N4 N 1.0799(4) -0.0448(5) 0.09607(12) 0.0641(7) Uani 1 1 d . . . . .
N5 N 1.2716(5) 0.7308(6) 0.45446(14) 0.0780(8) Uani 1 1 d . . . . .
N6 N 1.2564(6) 0.8919(6) 0.49080(19) 0.1106(12) Uani 1 1 d . . . . .
C1 C 1.0463(5) 0.4539(5) 0.38348(13) 0.0599(8) Uani 1 1 d . . . . .
C2 C 1.2750(6) 0.5421(6) 0.41139(16) 0.0675(9) Uani 1 1 d . . . . .
C4 C 1.0481(5) 0.2458(5) 0.33292(13) 0.0542(7) Uani 1 1 d . . . . .
C5 C 0.8577(5) 0.1327(5) 0.29673(14) 0.0544(7) Uani 1 1 d . . . . .
C6 C 0.9014(5) -0.2089(5) 0.12653(14) 0.0533(7) Uani 1 1 d . . . . .
C7 C 0.8341(4) -0.1933(5) 0.20079(13) 0.0516(7) Uani 1 1 d . . . . .
C8 C 0.6541(5) -0.3413(5) 0.22364(15) 0.0630(8) Uani 1 1 d . . . . .
H8 H 0.607975 -0.333479 0.273147 0.076 Uiso 1 1 calc R U . . .
C9 C 0.5412(5) -0.5009(6) 0.17443(17) 0.0716(9) Uani 1 1 d . . . . .
H9 H 0.416295 -0.596938 0.190255 0.086 Uiso 1 1 calc R U . . .
C10 C 0.6131(6) -0.5182(5) 0.10197(17) 0.0701(9) Uani 1 1 d . . . . .
H10 H 0.539048 -0.629206 0.069166 0.084 Uiso 1 1 calc R U . . .
C3 C 0.7940(5) -0.3728(6) 0.07712(15) 0.0661(8) Uani 1 1 d . . . . .
H3 H 0.842651 -0.385085 0.027957 0.079 Uiso 1 1 calc R U . . .
H5 H 0.700(5) 0.148(4) 0.2994(12) 0.058(8) Uiso 1 1 d . . . . .
H2 H 1.427(5) 0.484(5) 0.4016(13) 0.070(9) Uiso 1 1 d . . . . .
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
N2 N1 C7 120.3(2) . . ?
C5 N1 N2 110.6(2) . . ?
C5 N1 C7 129.1(2) . . ?
N3 N2 N1 106.7(2) . . ?
N2 N3 C4 109.2(2) . . ?
O1 N4 O2 124.7(3) . . ?
O1 N4 C6 117.6(2) . . ?
O2 N4 C6 117.6(3) . . ?
N6 N5 C2 176.5(3) . . ?
O3 C1 C2 124.0(3) . . ?
O3 C1 C4 120.4(3) . . ?
C2 C1 C4 115.6(3) . . ?
N5 C2 C1 115.1(3) . . ?
N5 C2 H2 116.6(16) . . ?
C1 C2 H2 128.3(16) . . ?
N3 C4 C1 123.8(2) . . ?
N3 C4 C5 108.4(2) . . ?
C5 C4 C1 127.6(2) . . ?
N1 C5 C4 105.0(2) . . ?
N1 C5 H5 122.5(16) . . ?
C4 C5 H5 132.4(16) . . ?
C7 C6 N4 122.0(2) . . ?
C3 C6 N4 117.0(2) . . ?
C3 C6 C7 121.0(3) . . ?
C6 C7 N1 121.3(2) . . ?
C8 C7 N1 120.1(2) . . ?
C8 C7 C6 118.6(2) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C3 120.7(3) . . ?
C3 C10 H10 119.6 . . ?
C6 C3 C10 118.8(3) . . ?
C6 C3 H3 120.6 . . ?
C10 C3 H3 120.6 . . ?
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 N4 1.219(3) . ?
O2 N4 1.219(3) . ?
O3 C1 1.233(3) . ?
N1 N2 1.363(3) . ?
N1 C5 1.335(3) . ?
N1 C7 1.436(3) . ?
N2 N3 1.301(3) . ?
N3 C4 1.360(3) . ?
N4 C6 1.474(3) . ?
N5 N6 1.124(3) . ?
N5 C2 1.314(4) . ?
C1 C2 1.429(4) . ?
C1 C4 1.480(4) . ?
C2 H2 0.95(3) . ?
C4 C5 1.362(3) . ?
C5 H5 0.89(3) . ?
C6 C7 1.392(3) . ?
C6 C3 1.380(3) . ?
C7 C8 1.372(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(4) . ?
C10 H10 0.9300 . ?
C10 C3 1.380(4) . ?
C3 H3 0.9300 . ?
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
O1 N4 C6 C7 -37.6(4) . . . . ?
O1 N4 C6 C3 139.3(3) . . . . ?
O2 N4 C6 C7 145.5(3) . . . . ?
O2 N4 C6 C3 -37.6(4) . . . . ?
O3 C1 C2 N5 -1.9(5) . . . . ?
O3 C1 C4 N3 177.3(3) . . . . ?
O3 C1 C4 C5 2.6(5) . . . . ?
N1 N2 N3 C4 0.4(3) . . . . ?
N1 C7 C8 C9 -179.2(3) . . . . ?
N2 N1 C5 C4 0.8(3) . . . . ?
N2 N1 C7 C6 -52.2(4) . . . . ?
N2 N1 C7 C8 126.6(3) . . . . ?
N2 N3 C4 C1 -175.6(2) . . . . ?
N2 N3 C4 C5 0.1(3) . . . . ?
N3 C4 C5 N1 -0.6(3) . . . . ?
N4 C6 C7 N1 -6.0(4) . . . . ?
N4 C6 C7 C8 175.3(3) . . . . ?
N4 C6 C3 C10 -175.2(3) . . . . ?
C1 C4 C5 N1 174.9(3) . . . . ?
C2 C1 C4 N3 -2.7(4) . . . . ?
C2 C1 C4 C5 -177.5(3) . . . . ?
C4 C1 C2 N5 178.1(3) . . . . ?
C5 N1 N2 N3 -0.8(3) . . . . ?
C5 N1 C7 C6 125.6(3) . . . . ?
C5 N1 C7 C8 -55.6(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 N1 N2 N3 177.4(2) . . . . ?
C7 N1 C5 C4 -177.2(2) . . . . ?
C7 C6 C3 C10 1.7(4) . . . . ?
C7 C8 C9 C10 1.9(5) . . . . ?
C8 C9 C10 C3 -1.7(5) . . . . ?
C9 C10 C3 C6 -0.1(5) . . . . ?
C3 C6 C7 N1 177.3(2) . . . . ?
C3 C6 C7 C8 -1.5(4) . . . . ?
