# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_kotr993_0m
_database_code_depnum_ccdc_archive 'CCDC 2242839'
loop_
_audit_author_name
_audit_author_address
'Bezzubov S.I.'
;Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_audit_creation_date             2022-11-29
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
bezzubov@igic.ras.ru
_chemical_name_common            ?
_chemical_name_systematic        
N-Methyl-3-phenyl-5H-[1,2,3]triazolo[1,5-a][3,1]benzoxazin-5-imine
_chemical_formula_moiety         'C16 H12 N4 O'
_chemical_formula_sum            'C16 H12 N4 O'
_chemical_formula_weight         276.30
_chemical_melting_point          464-465
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   7.6681(5)
_cell_length_b                   12.2337(8)
_cell_length_c                   13.8648(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.657(2)
_cell_angle_gamma                90
_cell_volume                     1278.21(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5080
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.27
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.963
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3165
_reflns_number_total             4252
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_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)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.031
_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
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
