#------------------------------------------------------------------------------
#$Date: 2023-07-05 12:35:31 +0200 (Wed 05 de Jul de 2023) $
#$Revision: 284943 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/25/7062508.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_7062508
loop_
_publ_author_name
'Kotovshchikov, Yury N.'
'Tatevosyan, Stepan S.'
'Latyshev, Gennadij V.'
'Kugusheva, Zoya R.'
'Lukashev, Nikolay V.'
'Beletskaya, Irina P.'
_publ_section_title
;
 Divergent cyclization of 2-(5-iodo-1,2,3-triazolyl)benzamides toward
 triazole-fused lactams and cyclic imidates
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12239
_journal_page_last               12247
_journal_paper_doi               10.1039/D3NJ01264F
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C16 H12 N4 O'
_chemical_formula_sum            'C16 H12 N4 O'
_chemical_formula_weight         276.30
_chemical_melting_point          464.5(5)
_chemical_name_systematic
N-Methyl-3-phenyl-5H-[1,2,3]triazolo[1,5-a][3,1]benzoxazin-5-imine
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-29
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2023-02-17 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.657(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6681(5)
_cell_length_b                   12.2337(8)
_cell_length_c                   13.8648(8)
_cell_measurement_reflns_used    5080
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.27
_cell_measurement_theta_min      2.24
_cell_volume                     1278.21(14)
_computing_cell_refinement       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker AXS, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON III CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22327
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.568
_diffrn_reflns_theta_min         2.237
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1367 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.9369.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0472
_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)+(0.0544P)²+0.2984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3165
_reflns_number_total             4252
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01264f2.cif
_cod_data_source_block           mo_kotr993_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '464-465' was changed to
'464.5(5)' -- the average value was taken and precision was
estimated.

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7062508.cif.
;
_cod_database_code               7062508
_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_max   0.992
_shelx_estimated_absorpt_t_min   0.963
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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 0.72276(11) 0.48396(7) 0.55623(6) 0.01683(18) Uani 1 1 d . . . . .
N3 N 0.65461(13) 0.39885(8) 0.40104(7) 0.0160(2) Uani 1 1 d . . . . .
N4 N 0.65650(14) 0.39631(8) 0.69167(7) 0.0178(2) Uani 1 1 d . . . . .
N1 N 0.77167(15) 0.50597(9) 0.30889(8) 0.0212(2) Uani 1 1 d . . . . .
N2 N 0.68266(15) 0.41425(9) 0.30765(7) 0.0212(2) Uani 1 1 d . . . . .
C5 C 0.56910(15) 0.30634(9) 0.53559(8) 0.0144(2) Uani 1 1 d . . . . .
C2 C 0.72961(15) 0.48034(9) 0.45988(8) 0.0153(2) Uani 1 1 d . . . . .
C11 C 0.89660(16) 0.65470(10) 0.42445(9) 0.0186(2) Uani 1 1 d . . . . .
C10 C 0.56974(15) 0.30835(9) 0.43502(8) 0.0153(2) Uani 1 1 d . . . . .
C6 C 0.49451(16) 0.21584(10) 0.57418(9) 0.0169(2) Uani 1 1 d . . . . .
C1 C 0.80404(16) 0.55058(10) 0.40141(9) 0.0173(2) Uani 1 1 d . . . . .
C7 C 0.42032(17) 0.13246(10) 0.51274(9) 0.0186(2) Uani 1 1 d . . . . .
C3 C 0.65002(15) 0.39515(9) 0.60055(8) 0.0142(2) Uani 1 1 d . . . . .
C8 C 0.42076(17) 0.13682(10) 0.41230(9) 0.0198(2) Uani 1 1 d . . . . .
C9 C 0.49663(17) 0.22462(10) 0.37254(9) 0.0189(2) Uani 1 1 d . . . . .
C4 C 0.74695(19) 0.48679(11) 0.74902(9) 0.0211(3) Uani 1 1 d . . . . .
C16 C 0.94263(17) 0.71853(11) 0.34916(10) 0.0236(3) Uani 1 1 d . . . . .
C12 C 0.93859(17) 0.69288(10) 0.52112(10) 0.0217(3) Uani 1 1 d . . . . .
C13 C 1.02289(18) 0.79310(11) 0.54147(12) 0.0266(3) Uani 1 1 d . . . . .
C15 C 1.02904(18) 0.81765(11) 0.37058(12) 0.0289(3) Uani 1 1 d . . . . .
C14 C 1.06801(18) 0.85538(11) 0.46643(12) 0.0297(3) Uani 1 1 d . . . . .
H6 H 0.498(2) 0.2128(12) 0.6457(11) 0.021(4) Uiso 1 1 d . . . . .
H7 H 0.369(2) 0.0707(13) 0.5396(11) 0.023(4) Uiso 1 1 d . . . . .
H12 H 0.909(2) 0.6463(13) 0.5772(11) 0.027(4) Uiso 1 1 d . . . . .
H15 H 1.062(2) 0.8621(15) 0.3163(13) 0.037(5) Uiso 1 1 d . . . . .
H16 H 0.914(2) 0.6923(13) 0.2824(12) 0.026(4) Uiso 1 1 d . . . . .
H8 H 0.370(2) 0.0770(13) 0.3680(11) 0.024(4) Uiso 1 1 d . . . . .
H4A H 0.877(3) 0.4864(14) 0.7486(13) 0.040(5) Uiso 1 1 d . . . . .
H9 H 0.502(2) 0.2304(12) 0.3037(11) 0.024(4) Uiso 1 1 d . . . . .
H4B H 0.697(2) 0.5604(14) 0.7262(12) 0.032(4) Uiso 1 1 d . . . . .
H4C H 0.733(2) 0.4774(14) 0.8183(13) 0.035(5) Uiso 1 1 d . . . . .
H13 H 1.053(2) 0.8181(14) 0.6118(13) 0.038(5) Uiso 1 1 d . . . . .
H14 H 1.130(2) 0.9247(14) 0.4817(12) 0.033(4) 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
C2 O1 C3 119.80(9) . . ?
N2 N3 C10 126.12(10) . . ?
C2 N3 N2 110.35(10) . . ?
C2 N3 C10 123.42(10) . . ?
C3 N4 C4 118.87(10) . . ?
N2 N1 C1 110.85(10) . . ?
N1 N2 N3 106.17(10) . . ?
C10 C5 C6 118.28(10) . . ?
C10 C5 C3 121.27(10) . . ?
C6 C5 C3 120.42(10) . . ?
O1 C2 N3 122.27(10) . . ?
O1 C2 C1 131.31(11) . . ?
N3 C2 C1 106.41(10) . . ?
C16 C11 C1 120.09(12) . . ?
C12 C11 C1 121.03(11) . . ?
C12 C11 C16 118.87(12) . . ?
C5 C10 N3 115.79(10) . . ?
C9 C10 N3 121.91(10) . . ?
C9 C10 C5 122.27(11) . . ?
C5 C6 H6 118.5(9) . . ?
C7 C6 C5 119.99(11) . . ?
C7 C6 H6 121.5(9) . . ?
N1 C1 C2 106.20(11) . . ?
N1 C1 C11 123.08(11) . . ?
C2 C1 C11 130.70(11) . . ?
C6 C7 C8 120.70(11) . . ?
C6 C7 H7 119.6(9) . . ?
C8 C7 H7 119.7(9) . . ?
O1 C3 C5 117.18(9) . . ?
N4 C3 O1 118.93(10) . . ?
N4 C3 C5 123.89(10) . . ?
C7 C8 H8 121.2(9) . . ?
C9 C8 C7 120.43(11) . . ?
C9 C8 H8 118.3(9) . . ?
C10 C9 H9 118.4(9) . . ?
C8 C9 C10 118.32(11) . . ?
C8 C9 H9 123.3(9) . . ?
N4 C4 H4A 111.6(10) . . ?
N4 C4 H4B 113.0(10) . . ?
N4 C4 H4C 108.3(10) . . ?
H4A C4 H4B 109.1(14) . . ?
H4A C4 H4C 106.9(14) . . ?
H4B C4 H4C 107.7(13) . . ?
C11 C16 H16 118.9(10) . . ?
C15 C16 C11 120.27(13) . . ?
C15 C16 H16 120.8(10) . . ?
C11 C12 H12 119.8(9) . . ?
C13 C12 C11 120.30(12) . . ?
C13 C12 H12 119.8(9) . . ?
C12 C13 H13 118.5(10) . . ?
C14 C13 C12 120.29(14) . . ?
C14 C13 H13 121.2(10) . . ?
C16 C15 H15 119.5(10) . . ?
C14 C15 C16 120.40(13) . . ?
C14 C15 H15 120.1(10) . . ?
C13 C14 C15 119.85(13) . . ?
C13 C14 H14 119.6(10) . . ?
C15 C14 H14 120.5(10) . . ?
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 C2 1.3473(13) . ?
O1 C3 1.4128(13) . ?
N3 N2 1.3644(14) . ?
N3 C2 1.3477(15) . ?
N3 C10 1.4087(15) . ?
N4 C3 1.2551(15) . ?
N4 C4 1.4609(15) . ?
N1 N2 1.3118(15) . ?
N1 C1 1.3738(16) . ?
C5 C10 1.3956(15) . ?
C5 C6 1.3973(16) . ?
C5 C3 1.4730(16) . ?
C2 C1 1.3756(16) . ?
C11 C1 1.4644(17) . ?
C11 C16 1.4001(17) . ?
C11 C12 1.3996(18) . ?
C10 C9 1.3908(16) . ?
C6 C7 1.3822(17) . ?
C6 H6 0.988(15) . ?
C7 C8 1.3942(17) . ?
C7 H7 0.960(16) . ?
C8 C9 1.3837(18) . ?
C8 H8 0.989(15) . ?
C9 H9 0.966(15) . ?
C4 H4A 1.001(19) . ?
C4 H4B 1.007(17) . ?
C4 H4C 0.993(18) . ?
C16 C15 1.387(2) . ?
C16 H16 0.966(16) . ?
C12 C13 1.3905(18) . ?
C12 H12 1.024(16) . ?
C13 C14 1.384(2) . ?
C13 H13 1.007(18) . ?
C15 C14 1.386(2) . ?
C15 H15 0.999(17) . ?
C14 H14 0.977(17) . ?
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 C2 C1 N1 179.73(11) . . . . ?
O1 C2 C1 C11 -2.0(2) . . . . ?
N3 C2 C1 N1 -0.91(13) . . . . ?
N3 C2 C1 C11 177.38(11) . . . . ?
N3 C10 C9 C8 177.89(11) . . . . ?
N2 N3 C2 O1 -179.28(10) . . . . ?
N2 N3 C2 C1 1.29(13) . . . . ?
N2 N3 C10 C5 175.01(10) . . . . ?
N2 N3 C10 C9 -2.91(18) . . . . ?
N2 N1 C1 C2 0.22(14) . . . . ?
N2 N1 C1 C11 -178.23(10) . . . . ?
C5 C10 C9 C8 0.11(18) . . . . ?
C5 C6 C7 C8 0.77(18) . . . . ?
C2 O1 C3 N4 174.82(10) . . . . ?
C2 O1 C3 C5 -5.65(14) . . . . ?
C2 N3 N2 N1 -1.16(13) . . . . ?
C2 N3 C10 C5 -0.84(16) . . . . ?
C2 N3 C10 C9 -178.76(11) . . . . ?
C11 C16 C15 C14 -1.09(19) . . . . ?
C11 C12 C13 C14 -0.81(19) . . . . ?
C10 N3 N2 N1 -177.46(11) . . . . ?
C10 N3 C2 O1 -2.86(17) . . . . ?
C10 N3 C2 C1 177.72(10) . . . . ?
C10 C5 C6 C7 -1.44(17) . . . . ?
C10 C5 C3 O1 2.07(15) . . . . ?
C10 C5 C3 N4 -178.41(11) . . . . ?
C6 C5 C10 N3 -176.89(10) . . . . ?
C6 C5 C10 C9 1.01(17) . . . . ?
C6 C5 C3 O1 179.99(10) . . . . ?
C6 C5 C3 N4 -0.50(17) . . . . ?
C6 C7 C8 C9 0.39(19) . . . . ?
C1 N1 N2 N3 0.55(13) . . . . ?
C1 C11 C16 C15 179.47(11) . . . . ?
C1 C11 C12 C13 -178.52(11) . . . . ?
C7 C8 C9 C10 -0.82(18) . . . . ?
C3 O1 C2 N3 6.19(16) . . . . ?
C3 O1 C2 C1 -174.55(12) . . . . ?
C3 C5 C10 N3 1.07(16) . . . . ?
C3 C5 C10 C9 178.97(11) . . . . ?
C3 C5 C6 C7 -179.42(11) . . . . ?
C4 N4 C3 O1 -3.05(16) . . . . ?
C4 N4 C3 C5 177.45(11) . . . . ?
C16 C11 C1 N1 5.75(18) . . . . ?
C16 C11 C1 C2 -172.29(12) . . . . ?
C16 C11 C12 C13 0.68(18) . . . . ?
C16 C15 C14 C13 1.0(2) . . . . ?
C12 C11 C1 N1 -175.06(11) . . . . ?
C12 C11 C1 C2 6.9(2) . . . . ?
C12 C11 C16 C15 0.26(18) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
