# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_exp_22
_database_code_depnum_ccdc_archive 'CCDC 2196103'
loop_
_audit_author_name
_audit_author_address
'Slepukhin P.A.'
;Ural Federal University
Russia
;
_audit_update_record             
;
2022-08-10 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_date             2022-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_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      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                   9.3597(8)
_cell_length_b                   18.0931(15)
_cell_length_c                   7.4440(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.260(8)
_cell_angle_gamma                90
_cell_volume                     1253.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1963
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.4110
_cell_measurement_theta_min      4.0280
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'greenish brown'
_exptl_crystal_colour_modifier   green
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.472
_diffrn_reflns_theta_min         3.868
_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 0.991
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  67.00   1.00   30.00    --   21.45  25.00  60.00   34
  2  ω    -50.00  52.00   1.00   30.00    --   21.45 -25.00-103.00  102
  3  ω    -26.00  -1.00   1.00   30.00    --  -23.01  25.00  60.00   25
  4  ω    -73.00 -47.00   1.00   30.00    --  -23.01 -25.00-103.00   26
  5  ω     40.00  95.00   1.00   30.00    --   21.45 178.00-120.00   55
  6  ω    -91.00 -37.00   1.00   30.00    --  -23.01 -57.00-150.00   54
;
_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      -0.0604768000
_diffrn_orient_matrix_UB_12      -0.0121611000
_diffrn_orient_matrix_UB_13      0.0417423000
_diffrn_orient_matrix_UB_21      0.0390521000
_diffrn_orient_matrix_UB_22      0.0049028000
_diffrn_orient_matrix_UB_23      0.0862844000
_diffrn_orient_matrix_UB_31      -0.0251487000
_diffrn_orient_matrix_UB_32      0.0369192000
_diffrn_orient_matrix_UB_33      0.0022818000
_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                1608
_reflns_number_total             3371
_reflns_odcompleteness_completeness 98.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.272
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      1.022
_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)+(0.1100P)²+0.0250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.2367
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_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 0.62931(16) 0.30147(8) 0.6988(2) 0.0589(5) Uani 1 1 d . . . . .
N1 N 0.9106(2) 0.14434(11) 0.5807(3) 0.0702(6) Uani 1 1 d . . . . .
C2 C 0.5302(2) 0.34857(13) 0.7555(3) 0.0552(6) Uani 1 1 d . . . . .
C5 C 0.7668(3) 0.40318(13) 0.6154(3) 0.0558(6) Uani 1 1 d . . . . .
C6 C 0.7503(2) 0.32875(13) 0.6328(3) 0.0542(6) Uani 1 1 d . . . . .
C4 C 0.6648(2) 0.45347(12) 0.6671(3) 0.0537(6) Uani 1 1 d . . . . .
C3 C 0.5450(2) 0.42148(14) 0.7438(3) 0.0566(6) Uani 1 1 d . . . . .
C8 C 0.8248(3) 0.20098(13) 0.6136(3) 0.0600(6) Uani 1 1 d . . . . .
C7 C 0.8486(3) 0.27368(13) 0.5890(3) 0.0587(6) Uani 1 1 d . . . . .
C11 C 0.6753(3) 0.53011(13) 0.6457(3) 0.0589(6) Uani 1 1 d . . . . .
N2 N 0.4906(3) 0.61751(13) 0.7622(4) 0.0886(8) Uani 1 1 d . . . . .
C12 C 0.5743(3) 0.57874(13) 0.7090(4) 0.0637(6) Uani 1 1 d . . . . .
C1 C 0.4096(3) 0.30766(13) 0.8238(4) 0.0735(8) Uani 1 1 d . . . . .
H1A H 0.360631 0.278946 0.727525 0.110 Uiso 1 1 calc R U . . .
H1B H 0.343632 0.342175 0.867605 0.110 Uiso 1 1 calc R U . . .
H1C H 0.446558 0.275433 0.920258 0.110 Uiso 1 1 calc R U . . .
C13 C 0.7842(3) 0.56224(13) 0.5529(4) 0.0673(7) Uani 1 1 d . . . . .
N3 N 0.8709(3) 0.58852(15) 0.4753(4) 0.1014(10) Uani 1 1 d . . . . .
C10 C 0.8700(3) 0.06905(14) 0.6138(4) 0.0811(9) Uani 1 1 d . . . . .
H10A H 0.938306 0.047642 0.704552 0.122 Uiso 1 1 calc R U . . .
H10B H 0.868338 0.041033 0.504053 0.122 Uiso 1 1 calc R U . . .
H10C H 0.776205 0.068385 0.654734 0.122 Uiso 1 1 calc R U . . .
C9 C 1.0492(3) 0.15612(17) 0.5138(5) 0.0881(9) Uani 1 1 d . . . . .
H9A H 1.035664 0.182704 0.401650 0.132 Uiso 1 1 calc R U . . .
H9B H 1.093175 0.109237 0.494959 0.132 Uiso 1 1 calc R U . . .
H9C H 1.110105 0.184199 0.600750 0.132 Uiso 1 1 calc R U . . .
H5 H 0.855(3) 0.4195(12) 0.565(3) 0.059(6) Uiso 1 1 d . . . . .
H8 H 0.732(3) 0.1831(12) 0.656(3) 0.062(7) Uiso 1 1 d . . . . .
H3 H 0.474(3) 0.4511(12) 0.789(3) 0.067(7) Uiso 1 1 d . . . . .
H7 H 0.935(3) 0.2920(13) 0.534(4) 0.082(8) 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 1.360(3) . ?
O1 C6 1.374(3) . ?
N1 C8 1.341(3) . ?
N1 C10 1.443(3) . ?
N1 C9 1.455(4) . ?
C2 C3 1.330(3) . ?
C2 C1 1.485(3) . ?
C5 C6 1.363(3) . ?
C5 C4 1.403(3) . ?
C5 H5 0.99(2) . ?
C6 C7 1.419(3) . ?
C4 C3 1.435(3) . ?
C4 C11 1.400(3) . ?
C3 H3 0.94(2) . ?
C8 C7 1.350(3) . ?
C8 H8 1.01(3) . ?
C7 H7 1.00(3) . ?
C11 C12 1.410(3) . ?
C11 C13 1.417(3) . ?
N2 C12 1.153(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C13 N3 1.149(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C2 O1 C6 120.15(18) . . ?
C8 N1 C10 121.1(2) . . ?
C8 N1 C9 121.6(2) . . ?
C10 N1 C9 117.3(2) . . ?
O1 C2 C1 111.31(19) . . ?
C3 C2 O1 121.5(2) . . ?
C3 C2 C1 127.2(2) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 116.0(13) . . ?
C4 C5 H5 122.1(13) . . ?
O1 C6 C7 114.3(2) . . ?
C5 C6 O1 119.7(2) . . ?
C5 C6 C7 126.1(2) . . ?
C5 C4 C3 115.6(2) . . ?
C11 C4 C5 123.6(2) . . ?
C11 C4 C3 120.8(2) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 117.3(15) . . ?
C4 C3 H3 121.5(15) . . ?
N1 C8 C7 127.5(2) . . ?
N1 C8 H8 111.5(13) . . ?
C7 C8 H8 121.0(13) . . ?
C6 C7 H7 115.8(14) . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 H7 122.0(14) . . ?
C4 C11 C12 121.5(2) . . ?
C4 C11 C13 121.7(2) . . ?
C12 C11 C13 116.8(2) . . ?
N2 C12 C11 178.8(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C13 C11 178.9(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O1 C2 C3 C4 1.3(4) . . . . ?
O1 C6 C7 C8 -1.0(3) . . . . ?
N1 C8 C7 C6 -178.6(2) . . . . ?
C2 O1 C6 C5 -3.5(3) . . . . ?
C2 O1 C6 C7 176.30(19) . . . . ?
C5 C6 C7 C8 178.8(2) . . . . ?
C5 C4 C3 C2 -3.1(3) . . . . ?
C5 C4 C11 C12 -176.4(2) . . . . ?
C5 C4 C11 C13 6.3(4) . . . . ?
C6 O1 C2 C3 2.1(3) . . . . ?
C6 O1 C2 C1 -179.2(2) . . . . ?
C6 C5 C4 C3 1.7(3) . . . . ?
C6 C5 C4 C11 -177.7(2) . . . . ?
C4 C5 C6 O1 1.5(3) . . . . ?
C4 C5 C6 C7 -178.2(2) . . . . ?
C3 C4 C11 C12 4.2(4) . . . . ?
C3 C4 C11 C13 -173.1(2) . . . . ?
C11 C4 C3 C2 176.3(2) . . . . ?
C1 C2 C3 C4 -177.2(2) . . . . ?
C10 N1 C8 C7 -179.9(3) . . . . ?
C9 N1 C8 C7 1.3(4) . . . . ?


_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 1.379
_oxdiff_exptl_absorpt_empirical_full_min 0.818
