# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1m
_database_code_depnum_ccdc_archive 'CCDC 2307246'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_audit_creation_date             2023-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H14 N6 O'
_chemical_formula_sum            'C16 H14 N6 O'
_chemical_formula_weight         306.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H14 N6 O'
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                   6.6228(4)
_cell_length_b                   10.0408(8)
_cell_length_c                   22.0134(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.015(5)
_cell_angle_gamma                90
_cell_volume                     1460.25(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1066
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.3960
_cell_measurement_theta_min      3.4390
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8883
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.986
_diffrn_reflns_theta_max         24.986
_diffrn_reflns_theta_min         3.083
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  43.00   1.00   50.00    --   18.92 -67.00-136.00   92
  2  ω     -5.00  87.00   1.00   50.00    --   18.92  67.00  -2.00   92
  3  ω    -11.00  19.00   1.00   50.00    --  -17.67 -99.00 120.00   30
  4  ω     -6.00  19.00   1.00   50.00    --  -17.67 -99.00   0.00   25
  5  ω     43.00  69.00   1.00   50.00    --   18.92 178.00 -90.00   26
  6  ω     -6.00  91.00   1.00   50.00    --   18.92  37.00 150.00   97
;
_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      -0.0391689000
_diffrn_orient_matrix_UB_12      0.0632534000
_diffrn_orient_matrix_UB_13      -0.0090698000
_diffrn_orient_matrix_UB_21      -0.0675038000
_diffrn_orient_matrix_UB_22      -0.0023416000
_diffrn_orient_matrix_UB_23      0.0236129000
_diffrn_orient_matrix_UB_31      0.0737176000
_diffrn_orient_matrix_UB_32      0.0313850000
_diffrn_orient_matrix_UB_33      0.0200836000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1604
_reflns_number_total             2566
_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_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0652
_refine_ls_restrained_S_all      1.078
_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)+(0.0599P)²+0.4751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.6813(5) 0.6165(3) 0.31480(12) 0.0856(9) Uani 1 1 d . . . . .
N1 N 0.5428(4) 0.7590(3) 0.54028(13) 0.0630(8) Uani 1 1 d . . . . .
N2 N 0.7293(5) 0.9460(3) 0.54690(12) 0.0592(8) Uani 1 1 d . . . . .
H2 H 0.825(5) 1.012(4) 0.5376(14) 0.066(10) Uiso 1 1 d . . . . .
N3 N 1.0093(5) 0.8144(3) 0.46156(13) 0.0662(8) Uani 1 1 d . . . . .
N4 N 1.0808(5) 0.7367(3) 0.42001(14) 0.0686(9) Uani 1 1 d . . . . .
N5 N 0.9464(5) 0.6320(3) 0.41206(13) 0.0634(8) Uani 1 1 d . . . . .
N6 N 0.6384(7) 0.5601(4) 0.4531(2) 0.0892(13) Uani 1 1 d . . . . .
H6A H 0.637(7) 0.497(5) 0.433(2) 0.098(17) Uiso 1 1 d . . . . .
H6B H 0.530(8) 0.585(5) 0.477(2) 0.126(19) Uiso 1 1 d . . . . .
C1 C 0.4532(5) 0.8502(4) 0.57744(15) 0.0594(9) Uani 1 1 d . . . . .
C2 C 0.2751(6) 0.8394(4) 0.60697(17) 0.0692(10) Uani 1 1 d . . . . .
H2A H 0.198022 0.761917 0.604424 0.083 Uiso 1 1 calc R U . . .
C3 C 0.2166(6) 0.9471(4) 0.64002(17) 0.0730(11) Uani 1 1 d . . . . .
H3 H 0.098054 0.942141 0.660184 0.088 Uiso 1 1 calc R U . . .
C4 C 0.3314(6) 1.0635(4) 0.64396(17) 0.0700(11) Uani 1 1 d . . . . .
H4 H 0.286789 1.134531 0.666607 0.084 Uiso 1 1 calc R U . . .
C5 C 0.5082(6) 1.0767(4) 0.61547(16) 0.0650(10) Uani 1 1 d . . . . .
H5 H 0.584740 1.154421 0.618362 0.078 Uiso 1 1 calc R U . . .
C6 C 0.5664(5) 0.9679(4) 0.58219(14) 0.0565(9) Uani 1 1 d . . . . .
C7 C 0.7063(5) 0.8219(4) 0.52240(15) 0.0567(9) Uani 1 1 d . . . . .
C8 C 0.8355(5) 0.7632(3) 0.48075(15) 0.0575(9) Uani 1 1 d . . . . .
C9 C 0.7920(6) 0.6465(4) 0.44883(15) 0.0613(9) Uani 1 1 d . . . . .
C10 C 0.9722(6) 0.5322(4) 0.36711(15) 0.0603(9) Uani 1 1 d . . . . .
C11 C 1.1325(6) 0.4441(4) 0.37440(19) 0.0749(11) Uani 1 1 d . . . . .
H11 H 1.222874 0.448610 0.408641 0.090 Uiso 1 1 calc R U . . .
C12 C 1.1565(7) 0.3488(5) 0.3298(2) 0.0890(13) Uani 1 1 d . . . . .
H12 H 1.264562 0.289507 0.333629 0.107 Uiso 1 1 calc R U . . .
C13 C 1.0216(8) 0.3423(5) 0.2805(2) 0.0845(13) Uani 1 1 d . . . . .
H13 H 1.039284 0.278096 0.250859 0.101 Uiso 1 1 calc R U . . .
C14 C 0.8600(7) 0.4277(4) 0.27300(18) 0.0796(12) Uani 1 1 d . . . . .
H14 H 0.768457 0.420464 0.239148 0.096 Uiso 1 1 calc R U . . .
C15 C 0.8347(6) 0.5255(4) 0.31685(16) 0.0656(10) Uani 1 1 d . . . . .
C16 C 0.5234(7) 0.6059(5) 0.2685(2) 0.0974(15) Uani 1 1 d . . . . .
H16A H 0.574671 0.626609 0.229859 0.146 Uiso 1 1 calc R U . . .
H16B H 0.417282 0.667229 0.276514 0.146 Uiso 1 1 calc R U . . .
H16C H 0.470980 0.516758 0.267581 0.146 Uiso 1 1 calc R U . . .


_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 C15 1.365(4) . ?
O1 C16 1.412(4) . ?
N1 C1 1.388(4) . ?
N1 C7 1.336(4) . ?
N2 H2 0.95(4) . ?
N2 C6 1.390(4) . ?
N2 C7 1.362(4) . ?
N3 N4 1.315(4) . ?
N3 C8 1.355(4) . ?
N4 N5 1.381(4) . ?
N5 C9 1.355(4) . ?
N5 C10 1.427(4) . ?
N6 H6A 0.77(5) . ?
N6 H6B 0.96(5) . ?
N6 C9 1.345(5) . ?
C1 C2 1.391(5) . ?
C1 C6 1.399(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(5) . ?
C7 C8 1.425(5) . ?
C8 C9 1.386(5) . ?
C10 C11 1.383(5) . ?
C10 C15 1.385(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.358(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.395(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C15 O1 C16 119.0(3) . . ?
C7 N1 C1 104.5(3) . . ?
C6 N2 H2 124(2) . . ?
C7 N2 H2 128(2) . . ?
C7 N2 C6 107.2(3) . . ?
N4 N3 C8 110.3(3) . . ?
N3 N4 N5 106.2(3) . . ?
N4 N5 C10 121.0(3) . . ?
C9 N5 N4 110.5(3) . . ?
C9 N5 C10 128.4(3) . . ?
H6A N6 H6B 124(5) . . ?
C9 N6 H6A 118(4) . . ?
C9 N6 H6B 118(3) . . ?
N1 C1 C2 129.5(3) . . ?
N1 C1 C6 110.6(3) . . ?
C2 C1 C6 119.9(3) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 H2A 121.1 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.1(4) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 121.9 . . ?
C4 C5 C6 116.3(4) . . ?
C6 C5 H5 121.9 . . ?
N2 C6 C1 104.9(3) . . ?
C5 C6 N2 132.5(3) . . ?
C5 C6 C1 122.6(3) . . ?
N1 C7 N2 112.7(3) . . ?
N1 C7 C8 122.0(3) . . ?
N2 C7 C8 125.3(3) . . ?
N3 C8 C7 127.2(3) . . ?
N3 C8 C9 108.3(3) . . ?
C9 C8 C7 124.3(3) . . ?
N5 C9 C8 104.7(3) . . ?
N6 C9 N5 125.4(4) . . ?
N6 C9 C8 129.9(4) . . ?
C11 C10 N5 119.8(3) . . ?
C11 C10 C15 121.2(3) . . ?
C15 C10 N5 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.9(4) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.0(4) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.2(4) . . ?
C15 C14 H14 120.4 . . ?
O1 C15 C10 116.1(3) . . ?
O1 C15 C14 125.0(4) . . ?
C10 C15 C14 118.9(4) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N1 C1 C2 C3 -178.2(3) . . . . ?
N1 C1 C6 N2 -0.2(4) . . . . ?
N1 C1 C6 C5 178.5(3) . . . . ?
N1 C7 C8 N3 -176.8(3) . . . . ?
N1 C7 C8 C9 9.1(6) . . . . ?
N2 C7 C8 N3 5.1(6) . . . . ?
N2 C7 C8 C9 -169.0(3) . . . . ?
N3 N4 N5 C9 0.2(4) . . . . ?
N3 N4 N5 C10 176.3(3) . . . . ?
N3 C8 C9 N5 1.0(4) . . . . ?
N3 C8 C9 N6 178.5(4) . . . . ?
N4 N3 C8 C7 -175.7(3) . . . . ?
N4 N3 C8 C9 -0.9(4) . . . . ?
N4 N5 C9 N6 -178.4(4) . . . . ?
N4 N5 C9 C8 -0.7(4) . . . . ?
N4 N5 C10 C11 69.0(5) . . . . ?
N4 N5 C10 C15 -111.2(4) . . . . ?
N5 C10 C11 C12 -179.2(3) . . . . ?
N5 C10 C15 O1 -0.6(5) . . . . ?
N5 C10 C15 C14 -179.9(3) . . . . ?
C1 N1 C7 N2 1.5(4) . . . . ?
C1 N1 C7 C8 -176.9(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C1 C6 N2 -178.9(3) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 N2 178.2(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C6 N2 C7 N1 -1.7(4) . . . . ?
C6 N2 C7 C8 176.6(3) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C7 N1 C1 C2 177.7(4) . . . . ?
C7 N1 C1 C6 -0.7(4) . . . . ?
C7 N2 C6 C1 1.1(4) . . . . ?
C7 N2 C6 C5 -177.4(4) . . . . ?
C7 C8 C9 N5 176.0(3) . . . . ?
C7 C8 C9 N6 -6.4(7) . . . . ?
C8 N3 N4 N5 0.4(4) . . . . ?
C9 N5 C10 C11 -115.7(4) . . . . ?
C9 N5 C10 C15 64.1(5) . . . . ?
C10 N5 C9 N6 5.9(6) . . . . ?
C10 N5 C9 C8 -176.4(3) . . . . ?
C10 C11 C12 C13 -0.9(6) . . . . ?
C11 C10 C15 O1 179.2(3) . . . . ?
C11 C10 C15 C14 -0.1(6) . . . . ?
C11 C12 C13 C14 -0.1(7) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C13 C14 C15 O1 179.8(4) . . . . ?
C13 C14 C15 C10 -0.9(6) . . . . ?
C15 C10 C11 C12 1.0(6) . . . . ?
C16 O1 C15 C10 -173.0(4) . . . . ?
C16 O1 C15 C14 6.3(6) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.951
_oxdiff_exptl_absorpt_empirical_full_min 0.501
####################################################################### 
# 
# 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_1t
_database_code_depnum_ccdc_archive 'CCDC 2307247'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_audit_creation_date             2023-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N6 O'
_chemical_formula_sum            'C16 H14 N6 O'
_chemical_formula_weight         306.33
_chemical_melting_point          ?
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3231(9)
_cell_length_b                   11.4404(19)
_cell_length_c                   12.235(2)
_cell_angle_alpha                73.954(15)
_cell_angle_beta                 81.185(14)
_cell_angle_gamma                89.683(14)
_cell_volume                     707.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1076
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.5370
_cell_measurement_theta_min      3.6180
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       stick
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2484
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.482
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  -6.00   1.00   20.00    --  -20.51 -57.00 -60.00   51
  2  ω    -24.00  19.00   1.00   20.00    --  -20.51 -99.00 120.00   43
  3  ω    -92.00 -35.00   1.00   20.00    --  -20.51-178.00 -30.00   57
  4  ω    -23.00   4.00   1.00   20.00    --  -20.51 -99.00 -90.00   27
  5  ω      4.00  48.00   1.00   20.00    --   21.76 -37.00 -30.00   44
  6  ω      0.00  87.00   1.00   20.00    --   21.76  57.00 -90.00   87
  7  ω    -44.00  58.00   1.00   20.00    --   21.76 -19.00  90.00  102
;
_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      -0.0500982000
_diffrn_orient_matrix_UB_12      -0.0457808000
_diffrn_orient_matrix_UB_13      0.0508524000
_diffrn_orient_matrix_UB_21      -0.0509489000
_diffrn_orient_matrix_UB_22      0.0454153000
_diffrn_orient_matrix_UB_23      0.0255138000
_diffrn_orient_matrix_UB_31      -0.1144739000
_diffrn_orient_matrix_UB_32      -0.0031279000
_diffrn_orient_matrix_UB_33      -0.0222425000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1579
_reflns_number_total             2484
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_reflns_special_details          
;
 _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_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0819
_refine_ls_restrained_S_all      1.028
_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)+(0.1147P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1984
_refine_ls_wR_factor_ref         0.2327
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.786(5)
 0.214(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.0445(5) 0.4379(2) 0.6687(2) 0.0499(8) Uani 1 1 d . . . . .
N1 N 0.6450(7) 0.2028(3) 0.3668(3) 0.0463(9) Uani 1 1 d . . . . .
N2 N 0.3221(6) 0.0778(3) 0.3676(3) 0.0379(8) Uani 1 1 d . . . . .
H2 H 0.192(11) 0.024(6) 0.395(5) 0.12(2) Uiso 1 1 d . . . . .
N3 N 0.0872(6) 0.1180(3) 0.5971(3) 0.0422(8) Uani 1 1 d . . . . .
N4 N 0.0425(6) 0.1594(3) 0.6876(3) 0.0444(9) Uani 1 1 d . . . . .
N5 N 0.2417(6) 0.2392(3) 0.6791(3) 0.0371(8) Uani 1 1 d . . . . .
N6 N 0.6203(7) 0.3217(3) 0.5472(4) 0.0482(10) Uani 1 1 d . . . . .
H6A H 0.731(13) 0.290(6) 0.482(6) 0.13(2) Uiso 1 1 d . . . . .
H6B H 0.688(9) 0.338(4) 0.603(4) 0.069(15) Uiso 1 1 d . . . . .
C1 C 0.6876(7) 0.1645(3) 0.2676(3) 0.0377(9) Uani 1 1 d . . . . .
C2 C 0.8903(8) 0.1905(4) 0.1769(4) 0.0474(11) Uani 1 1 d . . . . .
H2A H 1.025521 0.242165 0.175693 0.057 Uiso 1 1 calc R U . . .
C3 C 0.8846(8) 0.1375(4) 0.0896(4) 0.0473(10) Uani 1 1 d . . . . .
H3 H 1.018700 0.154010 0.028386 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6844(8) 0.0599(4) 0.0896(3) 0.0481(11) Uani 1 1 d . . . . .
H4 H 0.687851 0.025224 0.029086 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4808(8) 0.0336(4) 0.1782(3) 0.0424(10) Uani 1 1 d . . . . .
H5 H 0.345049 -0.017256 0.178296 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4873(7) 0.0858(3) 0.2665(3) 0.0353(9) Uani 1 1 d . . . . .
C7 C 0.4237(7) 0.1483(3) 0.4235(3) 0.0384(9) Uani 1 1 d . . . . .
C8 C 0.3125(7) 0.1677(3) 0.5312(3) 0.0365(9) Uani 1 1 d . . . . .
C9 C 0.4115(7) 0.2454(3) 0.5835(3) 0.0361(9) Uani 1 1 d . . . . .
C10 C 0.2510(7) 0.3071(3) 0.7603(3) 0.0362(9) Uani 1 1 d . . . . .
C11 C 0.4123(8) 0.2764(4) 0.8402(3) 0.0458(11) Uani 1 1 d . . . . .
H11 H 0.514354 0.209874 0.842217 0.055 Uiso 1 1 calc R U . . .
C12 C 0.4253(8) 0.3428(4) 0.9176(4) 0.0480(11) Uani 1 1 d . . . . .
H12 H 0.533518 0.321127 0.972267 0.058 Uiso 1 1 calc R U . . .
C13 C 0.2765(8) 0.4409(4) 0.9127(4) 0.0500(11) Uani 1 1 d . . . . .
H13 H 0.283165 0.485886 0.964991 0.060 Uiso 1 1 calc R U . . .
C14 C 0.1163(8) 0.4749(4) 0.8318(4) 0.0499(11) Uani 1 1 d . . . . .
H14 H 0.017436 0.542490 0.829747 0.060 Uiso 1 1 calc R U . . .
C15 C 0.1021(7) 0.4092(3) 0.7540(3) 0.0378(9) Uani 1 1 d . . . . .
C16 C -0.1828(9) 0.5479(4) 0.6554(4) 0.0597(13) Uani 1 1 d . . . . .
H16A H -0.265066 0.561518 0.588698 0.089 Uiso 1 1 calc R U . . .
H16B H -0.067139 0.615244 0.646254 0.089 Uiso 1 1 calc R U . . .
H16C H -0.308445 0.540336 0.722499 0.089 Uiso 1 1 calc R U . . .


_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 C15 1.365(4) . ?
O1 C16 1.437(5) . ?
N1 C1 1.387(5) . ?
N1 C7 1.333(5) . ?
N2 H2 0.89(6) . ?
N2 C6 1.384(5) . ?
N2 C7 1.354(5) . ?
N3 N4 1.310(4) . ?
N3 C8 1.367(5) . ?
N4 N5 1.376(4) . ?
N5 C9 1.350(5) . ?
N5 C10 1.427(4) . ?
N6 H6A 1.07(7) . ?
N6 H6B 0.88(5) . ?
N6 C9 1.357(5) . ?
C1 C2 1.392(5) . ?
C1 C6 1.404(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.371(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C7 C8 1.435(5) . ?
C8 C9 1.378(5) . ?
C10 C11 1.372(6) . ?
C10 C15 1.399(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C15 O1 C16 117.6(3) . . ?
C7 N1 C1 104.6(3) . . ?
C6 N2 H2 124(4) . . ?
C7 N2 H2 127(4) . . ?
C7 N2 C6 107.4(3) . . ?
N4 N3 C8 109.7(3) . . ?
N3 N4 N5 106.6(3) . . ?
N4 N5 C10 122.4(3) . . ?
C9 N5 N4 110.4(3) . . ?
C9 N5 C10 127.1(3) . . ?
H6A N6 H6B 122(5) . . ?
C9 N6 H6A 105(3) . . ?
C9 N6 H6B 115(3) . . ?
N1 C1 C2 130.5(4) . . ?
N1 C1 C6 110.2(3) . . ?
C2 C1 C6 119.3(4) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(4) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.1(4) . . ?
C6 C5 H5 121.4 . . ?
N2 C6 C1 104.9(3) . . ?
C5 C6 N2 132.5(3) . . ?
C5 C6 C1 122.6(4) . . ?
N1 C7 N2 112.9(3) . . ?
N1 C7 C8 121.2(3) . . ?
N2 C7 C8 126.0(3) . . ?
N3 C8 C7 126.7(3) . . ?
N3 C8 C9 108.1(3) . . ?
C9 C8 C7 125.1(3) . . ?
N5 C9 N6 124.6(3) . . ?
N5 C9 C8 105.1(3) . . ?
N6 C9 C8 130.1(3) . . ?
C11 C10 N5 120.7(4) . . ?
C11 C10 C15 120.2(3) . . ?
C15 C10 N5 119.1(3) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.9(4) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.7(4) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
O1 C15 C10 117.1(3) . . ?
O1 C15 C14 124.5(4) . . ?
C14 C15 C10 118.4(4) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N1 C1 C2 C3 178.8(4) . . . . ?
N1 C1 C6 N2 0.2(4) . . . . ?
N1 C1 C6 C5 -179.6(4) . . . . ?
N1 C7 C8 N3 179.6(4) . . . . ?
N1 C7 C8 C9 3.0(6) . . . . ?
N2 C7 C8 N3 0.7(6) . . . . ?
N2 C7 C8 C9 -176.0(4) . . . . ?
N3 N4 N5 C9 -0.9(4) . . . . ?
N3 N4 N5 C10 176.7(3) . . . . ?
N3 C8 C9 N5 0.1(4) . . . . ?
N3 C8 C9 N6 -174.7(4) . . . . ?
N4 N3 C8 C7 -177.8(4) . . . . ?
N4 N3 C8 C9 -0.7(4) . . . . ?
N4 N5 C9 N6 175.7(4) . . . . ?
N4 N5 C9 C8 0.4(4) . . . . ?
N4 N5 C10 C11 106.0(4) . . . . ?
N4 N5 C10 C15 -77.0(4) . . . . ?
N5 C10 C11 C12 178.9(3) . . . . ?
N5 C10 C15 O1 -0.2(5) . . . . ?
N5 C10 C15 C14 -179.0(3) . . . . ?
C1 N1 C7 N2 0.1(4) . . . . ?
C1 N1 C7 C8 -178.9(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C1 C6 N2 179.1(3) . . . . ?
C2 C1 C6 C5 -0.7(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C4 C5 C6 N2 -178.6(4) . . . . ?
C4 C5 C6 C1 1.1(6) . . . . ?
C6 N2 C7 N1 0.0(4) . . . . ?
C6 N2 C7 C8 179.0(4) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
C7 N1 C1 C2 -178.9(4) . . . . ?
C7 N1 C1 C6 -0.2(4) . . . . ?
C7 N2 C6 C1 -0.1(4) . . . . ?
C7 N2 C6 C5 179.7(4) . . . . ?
C7 C8 C9 N5 177.3(3) . . . . ?
C7 C8 C9 N6 2.5(7) . . . . ?
C8 N3 N4 N5 1.0(4) . . . . ?
C9 N5 C10 C11 -76.9(5) . . . . ?
C9 N5 C10 C15 100.1(5) . . . . ?
C10 N5 C9 N6 -1.8(6) . . . . ?
C10 N5 C9 C8 -177.0(3) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C11 C10 C15 O1 176.8(3) . . . . ?
C11 C10 C15 C14 -2.0(6) . . . . ?
C11 C12 C13 C14 -0.5(6) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C13 C14 C15 O1 -177.9(4) . . . . ?
C13 C14 C15 C10 0.8(6) . . . . ?
C15 C10 C11 C12 2.0(6) . . . . ?
C16 O1 C15 C10 -175.2(3) . . . . ?
C16 O1 C15 C14 3.5(6) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.657
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.786(5)
2 0.214(5)

