# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_cob-58
_database_code_depnum_ccdc_archive 'CCDC 2474620'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2025-07-21 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_audit_creation_date             2025-06-17
_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        2-chloro-N'-(pyridin-2-yloxy)benzimidamide
_chemical_formula_moiety         'C12 H10 Cl N3 O'
_chemical_formula_sum            'C12 H10 Cl N3 O'
_chemical_formula_weight         247.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H10 Cl N3 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.6695(2)
_cell_length_b                   9.7859(2)
_cell_length_c                   11.9081(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.892(3)
_cell_angle_gamma                90
_cell_volume                     1136.79(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4692
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7750
_cell_measurement_theta_min      4.5250
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    2.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.635
_diffrn_reflns_theta_min         4.533
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  32.00   0.50    0.70    --   41.10 -88.00 -94.00  112
  2  ω     42.00  67.00   0.50    0.70    --   41.10 -88.00 -94.00   50
  3  ω     38.00  63.00   0.50    2.30    --  100.00 -88.00 -94.00   50
  4  ω     89.00 127.00   0.50    2.30    --  100.00 -88.00 -94.00   76
  5  ω    -48.00   2.00   0.50    0.70    --  -41.10  54.00 -30.00  100
  6  ω   -105.00 -72.00   0.50    0.70    --  -41.10 -32.00 -30.00   66
  7  ω    -16.00  17.00   0.50    0.70    --  -41.10  88.00  22.00   66
  8  ω    -50.00  21.00   0.50    0.70    --  -41.10  32.00 150.00  142
  9  ω    -65.00 -34.00   0.50    0.70    --  -41.10 -32.00 -30.00   62
 10  ω    -50.00 -25.00   0.50    0.70    --  -41.10  88.00  22.00   50
 11  ω    -11.00  37.00   0.50    0.70    --   41.10 -54.00 -30.00   96
 12  ω     60.00  99.00   0.50    0.70    --   41.10  54.00  90.00   78
 13  ω     71.00 103.00   0.50    0.70    --   41.10  43.00 -30.00   64
 14  ω     31.00  68.00   0.50    0.70    --   41.10  43.00 -30.00   74
 15  ω     68.00  97.00   0.50    0.70    --   41.10  32.00-120.00   58
 16  ω     33.00  58.00   0.50    0.70    --   41.10  32.00-180.00   50
 17  ω     87.00 157.00   0.50    2.30    --  100.00  42.00  60.00  140
 18  ω     34.00  59.00   0.50    2.30    --  100.00 -87.00  30.00   50
 19  ω    102.00 128.00   0.50    2.30    --  100.00  93.00  60.00   52
 20  ω     50.00  76.00   0.50    2.30    --  100.00 -59.00 -90.00   52
 21  ω     95.00 121.00   0.50    2.30    --  100.00 -68.00-180.00   52
 22  ω     56.00  90.00   0.50    2.30    --  100.00 -68.00-180.00   68
 23  ω     52.00  94.00   0.50    2.30    --  100.00-133.00 120.00   84
 24  ω     90.00 118.00   0.50    2.30    --  100.00 -59.00 -60.00   56
 25  ω     48.00  82.00   0.50    2.30    --  100.00 -59.00 -60.00   68
 26  ω     82.00 148.00   0.50    2.30    --  100.00  59.00-180.00  132
 27  ω     98.00 152.00   0.50    2.30    --  100.00  25.00 -60.00  108
 28  ω    101.00 148.00   0.50    2.30    --  100.00  42.00 120.00   94
 29  ω     44.00  69.00   0.50    2.30    --  100.00 -77.00   0.00   50
 30  ω     83.00 109.00   0.50    2.30    --  100.00  59.00  90.00   52
 31  ω     87.00 155.00   0.50    2.30    --  100.00  68.00 150.00  136
 32  ω     87.00 125.00   0.50    2.30    --  100.00 -87.00  30.00   76
 33  ω    100.00 125.00   0.50    2.30    --  100.00  42.00 -60.00   50
 34  ω     66.00 103.00   0.50    2.30    --  100.00-111.00 -60.00   74
 35  ω     80.00 155.00   0.50    2.30    --  100.00  68.00 -60.00  150
 36  ω     84.00 139.00   0.50    2.30    --  100.00  59.00 -30.00  110
 37  ω    122.00 155.00   0.50    2.30    --  100.00  88.00  22.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1064503000
_diffrn_orient_matrix_UB_12      0.1145222000
_diffrn_orient_matrix_UB_13      0.0553404000
_diffrn_orient_matrix_UB_21      0.0684105000
_diffrn_orient_matrix_UB_22      -0.0836221000
_diffrn_orient_matrix_UB_23      0.1190282000
_diffrn_orient_matrix_UB_31      0.0944984000
_diffrn_orient_matrix_UB_32      -0.0684464000
_diffrn_orient_matrix_UB_33      -0.0527430000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1997
_reflns_number_total             2212
_reflns_odcompleteness_completeness 94.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_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         0.467
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+0.6312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0988
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C7(H7), C4(H4), C10(H10), C6(H6), C11(H11), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_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
Cl1 Cl 0.03436(4) 0.70474(5) 0.55831(4) 0.03002(15) Uani 1 1 d . . . . .
O1 O 0.19718(11) 0.39675(12) 0.33161(12) 0.0244(3) Uani 1 1 d . . . . .
N3 N 0.23147(14) 0.22757(14) 0.22249(13) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.25244(14) 0.52590(14) 0.39293(13) 0.0223(3) Uani 1 1 d . . . . .
N2 N 0.01537(14) 0.57552(15) 0.30176(13) 0.0233(3) Uani 1 1 d . . . . .
H2A H -0.010447 0.481722 0.261614 0.028 Uiso 1 1 calc R U . . .
H2B H -0.059027 0.646377 0.289991 0.028 Uiso 1 1 calc R U . . .
C8 C 0.29082(16) 0.32544(16) 0.30393(15) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.14705(16) 0.60567(17) 0.36999(14) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.18244(16) 0.74656(17) 0.42148(15) 0.0202(3) Uani 1 1 d . . . . .
C9 C 0.43119(16) 0.35165(17) 0.35442(15) 0.0215(3) Uani 1 1 d . . . . .
H9 H 0.476048 0.428759 0.424881 0.026 Uiso 1 1 calc R U . . .
C12 C 0.31144(18) 0.15369(18) 0.18235(17) 0.0255(4) Uani 1 1 d . . . . .
H12 H 0.264337 0.073386 0.115677 0.031 Uiso 1 1 calc R U . . .
C7 C 0.26995(17) 0.82641(18) 0.38698(16) 0.0227(4) Uani 1 1 d . . . . .
H7 H 0.309681 0.785109 0.323354 0.027 Uiso 1 1 calc R U . . .
C3 C 0.13390(16) 0.80256(17) 0.50421(16) 0.0218(3) Uani 1 1 d . . . . .
C4 C 0.16861(18) 0.93432(19) 0.54957(16) 0.0262(4) Uani 1 1 d . . . . .
H4 H 0.128556 0.976494 0.612645 0.031 Uiso 1 1 calc R U . . .
C10 C 0.51067(17) 0.27520(19) 0.31084(16) 0.0259(4) Uani 1 1 d . . . . .
H10 H 0.620286 0.293103 0.345978 0.031 Uiso 1 1 calc R U . . .
C6 C 0.30666(17) 0.95771(18) 0.43298(16) 0.0261(4) Uani 1 1 d . . . . .
H6 H 0.375406 1.017868 0.406097 0.031 Uiso 1 1 calc R U . . .
C11 C 0.45084(19) 0.17534(19) 0.22211(17) 0.0272(4) Uani 1 1 d . . . . .
H11 H 0.511603 0.116291 0.185260 0.033 Uiso 1 1 calc R U . . .
C5 C 0.25510(18) 1.01163(18) 0.51343(17) 0.0282(4) Uani 1 1 d . . . . .
H5 H 0.282471 1.114716 0.548307 0.034 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
Cl1 C3 1.7359(18) . ?
O1 N1 1.4593(17) . ?
O1 C8 1.364(2) . ?
N3 C8 1.327(2) . ?
N3 C12 1.345(2) . ?
N1 C1 1.304(2) . ?
N2 H2A 1.0200 . ?
N2 H2B 1.0200 . ?
N2 C1 1.340(2) . ?
C8 C9 1.393(2) . ?
C1 C2 1.494(2) . ?
C2 C7 1.401(2) . ?
C2 C3 1.397(2) . ?
C9 H9 1.0850 . ?
C9 C10 1.380(2) . ?
C12 H12 1.0850 . ?
C12 C11 1.382(3) . ?
C7 H7 1.0850 . ?
C7 C6 1.389(3) . ?
C3 C4 1.389(3) . ?
C4 H4 1.0850 . ?
C4 C5 1.389(3) . ?
C10 H10 1.0850 . ?
C10 C11 1.390(3) . ?
C6 H6 1.0850 . ?
C6 C5 1.388(3) . ?
C11 H11 1.0850 . ?
C5 H5 1.0850 . ?

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
C8 O1 N1 112.15(11) . . ?
C8 N3 C12 117.64(14) . . ?
C1 N1 O1 105.93(12) . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
O1 C8 C9 124.49(15) . . ?
N3 C8 O1 111.49(14) . . ?
N3 C8 C9 124.03(15) . . ?
N1 C1 N2 126.77(15) . . ?
N1 C1 C2 114.42(14) . . ?
N2 C1 C2 118.72(14) . . ?
C7 C2 C1 118.83(15) . . ?
C3 C2 C1 123.17(15) . . ?
C3 C2 C7 118.00(16) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 C8 117.05(16) . . ?
C10 C9 H9 121.5 . . ?
N3 C12 H12 118.5 . . ?
N3 C12 C11 123.04(16) . . ?
C11 C12 H12 118.5 . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.01(16) . . ?
C6 C7 H7 119.5 . . ?
C2 C3 Cl1 120.17(13) . . ?
C4 C3 Cl1 118.32(14) . . ?
C4 C3 C2 121.44(16) . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.40(17) . . ?
C5 C4 H4 120.3 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.26(16) . . ?
C11 C10 H10 119.9 . . ?
C7 C6 H6 120.1 . . ?
C5 C6 C7 119.77(16) . . ?
C5 C6 H6 120.1 . . ?
C12 C11 C10 117.85(16) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.36(17) . . ?
C6 C5 H5 119.8 . . ?

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
Cl1 C3 C4 C5 176.07(13) . . . . ?
O1 N1 C1 N2 -1.3(2) . . . . ?
O1 N1 C1 C2 -177.85(12) . . . . ?
O1 C8 C9 C10 -176.17(15) . . . . ?
N3 C8 C9 C10 3.8(3) . . . . ?
N3 C12 C11 C10 2.3(3) . . . . ?
N1 O1 C8 N3 -164.16(13) . . . . ?
N1 O1 C8 C9 15.8(2) . . . . ?
N1 C1 C2 C7 57.8(2) . . . . ?
N1 C1 C2 C3 -121.25(18) . . . . ?
N2 C1 C2 C7 -119.04(17) . . . . ?
N2 C1 C2 C3 61.9(2) . . . . ?
C8 O1 N1 C1 154.86(14) . . . . ?
C8 N3 C12 C11 0.1(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C1 C2 C7 C6 -179.56(15) . . . . ?
C1 C2 C3 Cl1 3.4(2) . . . . ?
C1 C2 C3 C4 -179.67(15) . . . . ?
C2 C7 C6 C5 -0.6(2) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C9 C10 C11 C12 -1.6(3) . . . . ?
C12 N3 C8 O1 176.73(14) . . . . ?
C12 N3 C8 C9 -3.2(2) . . . . ?
C7 C2 C3 Cl1 -175.74(12) . . . . ?
C7 C2 C3 C4 1.2(2) . . . . ?
C7 C6 C5 C4 0.9(3) . . . . ?
C3 C2 C7 C6 -0.4(2) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?

_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.643
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_105-003_end-088
_database_code_depnum_ccdc_archive 'CCDC 2474621'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2025-07-21 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_audit_creation_date             2025-06-17
_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        
3-(3-chlorophenyl)-4-(pyridin-2-yloxy)-1,2,4-thiadiazol-5(4H)-one
_chemical_formula_moiety         'C13 H8 Cl N3 O2 S'
_chemical_formula_sum            'C13 H8 Cl N3 O2 S'
_chemical_formula_weight         305.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H10ClN3O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   27.1298(12)
_cell_length_b                   6.4573(2)
_cell_length_c                   8.0989(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.245(5)
_cell_angle_gamma                90
_cell_volume                     1293.67(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.3360
_cell_measurement_theta_min      3.5690
_shelx_estimated_absorpt_T_max   0.634
_shelx_estimated_absorpt_T_min   0.489
_exptl_absorpt_coefficient_mu    4.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10275
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.402
_diffrn_reflns_theta_min         3.574
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  24.00   1.00    2.00    --  -47.14  52.00 142.00   47
  2  ω    -95.00 -44.00   1.00    2.00    --  -47.14 -52.00  -2.00   51
  3  ω     17.00  52.00   1.00    2.00    --   47.14 -52.00  -2.00   35
  4  ω     36.00 119.00   1.00    2.00    --   47.14  52.00 142.00   83
  5  ω   -176.00 -93.00   1.00    8.00    -- -106.00 -52.00  -2.00   83
  6  ω    -59.00 -34.00   1.00    8.00    -- -106.00  52.00 142.00   25
  7  ω    115.00 140.00   1.00    8.00    --  113.25  52.00 142.00   25
  8  ω    -40.00  26.00   1.00    2.00    --  -47.14  37.00 -60.00   66
  9  ω    -25.00  23.00   1.00    2.00    --  -47.14  19.00 -60.00   48
 10  ω     60.00  85.00   1.00    2.00    --   47.14  19.00   0.00   25
 11  ω    -26.00  13.00   1.00    2.00    --   47.14 -19.00   0.00   39
 12  ω    -70.00 -34.00   1.00    8.00    -- -106.00  61.00 -90.00   36
 13  ω    -92.00 -41.00   1.00    8.00    -- -106.00  77.00  60.00   51
 14  ω    -71.00 -35.00   1.00    8.00    -- -106.00  77.00-180.00   36
 15  ω   -149.00 -95.00   1.00    8.00    -- -106.00 -45.00 -90.00   54
 16  ω    -63.00 -36.00   1.00    8.00    -- -106.00  61.00 -30.00   27
 17  ω    -69.00 -36.00   1.00    8.00    -- -106.00  61.00-120.00   33
 18  ω    -69.00 -41.00   1.00    8.00    -- -106.00  61.00 120.00   28
 19  ω    -63.00 -37.00   1.00    8.00    -- -106.00  61.00 -60.00   26
 20  ω   -176.00 -92.00   1.00    8.00    -- -106.00 -61.00  90.00   84
 21  ω    -71.00 -46.00   1.00    8.00    -- -106.00  61.00-180.00   25
 22  ω    102.00 163.00   1.00    8.00    --  113.25  30.00-180.00   61
 23  ω     43.00  94.00   1.00    8.00    --  113.25 -77.00-120.00   51
 24  ω     42.00  67.00   1.00    8.00    --  113.25 -61.00  30.00   25
 25  ω     45.00  70.00   1.00    8.00    --  113.25 -61.00 -30.00   25
 26  ω     43.00  68.00   1.00    8.00    --  113.25 -61.00-120.00   25
 27  ω     44.00 107.00   1.00    8.00    --  113.25-125.00-180.00   63
 28  ω    104.00 165.00   1.00    8.00    --  113.25  30.00  90.00   61
 29  ω    111.00 136.00   1.00    8.00    --  113.25  45.00-120.00   25
 30  ω    102.00 162.00   1.00    8.00    --  113.25  77.00-180.00   60
 31  ω     42.00  67.00   1.00    8.00    --  113.25 -61.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0566526000
_diffrn_orient_matrix_UB_12      0.0530830000
_diffrn_orient_matrix_UB_13      -0.0113020000
_diffrn_orient_matrix_UB_21      -0.0098287000
_diffrn_orient_matrix_UB_22      0.1419185000
_diffrn_orient_matrix_UB_23      -0.1634463000
_diffrn_orient_matrix_UB_31      -0.0239157000
_diffrn_orient_matrix_UB_32      -0.1842933000
_diffrn_orient_matrix_UB_33      -0.1291718000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2537
_reflns_number_total             2716
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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         0.440
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2716
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.035
_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)+(0.0692P)²+1.9717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1374
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C8A-C7A = C6A-C7A
 1.384 with sigma of 0.02
 C6A-C7A
 1.384 with sigma of 0.002
 C7A-C8A
 1.384 with sigma of 0.02
 C5-C6A
 1.384 with sigma of 0.002
 C6-C5
 1.384 with sigma of 0.001
 C3-C8A
 1.384 with sigma of 0.001
 C8-C3
 1.384 with sigma of 0.001
 C6-C7 = C7-C8
 1.384 with sigma of 0.001
 C8A-C7A
 1.384 with sigma of 0.001
2. Others
 Sof(C6)=Sof(H6)=Sof(C8)=Sof(H8)=Sof(C7)=Sof(H7)=1-FVAR(1)
 Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(H6A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C4(H4), C6(H6), C8(H8), C7(H7), C8A(H8A), C7A(H7A),
 C6A(H6A)
;
_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
S1 S 0.41576(2) 0.65290(9) -0.04863(8) 0.02728(18) Uani 1 1 d . . . . .
Cl1 Cl 0.16987(3) 0.62615(16) 0.03819(13) 0.0607(3) Uani 1 1 d . . . . .
O2 O 0.48175(7) 0.3196(3) 0.0731(2) 0.0265(4) Uani 1 1 d . . . . .
O1 O 0.39787(7) 0.1132(3) 0.1100(2) 0.0254(4) Uani 1 1 d . . . . .
N3 N 0.43234(8) 0.3035(3) 0.3794(3) 0.0260(4) Uani 1 1 d . . . . .
N2 N 0.39231(8) 0.3067(3) 0.0309(3) 0.0251(4) Uani 1 1 d . . . . .
N1 N 0.35296(8) 0.6180(3) -0.0563(3) 0.0302(5) Uani 1 1 d . . . . .
C9 C 0.41832(9) 0.1233(4) 0.3001(3) 0.0231(5) Uani 1 1 d . . . . .
C10 C 0.42150(9) -0.0667(4) 0.3838(3) 0.0252(5) Uani 1 1 d . . . . .
H10 H 0.408700 -0.209262 0.307002 0.030 Uiso 1 1 calc R U . . .
C1 C 0.43808(9) 0.4012(4) 0.0290(3) 0.0232(5) Uani 1 1 d . . . . .
C11 C 0.44190(9) -0.0636(4) 0.5703(3) 0.0270(5) Uani 1 1 d . . . . .
H11 H 0.445582 -0.206355 0.645202 0.032 Uiso 1 1 calc R U . . .
C2 C 0.34764(9) 0.4320(4) -0.0092(3) 0.0279(5) Uani 1 1 d . . . . .
C13 C 0.45243(10) 0.3016(4) 0.5631(3) 0.0286(5) Uani 1 1 d . . . . .
C12 C 0.45768(10) 0.1230(4) 0.6615(3) 0.0286(5) Uani 1 1 d . . . . .
C3 C 0.29655(11) 0.3547(4) -0.0045(4) 0.0404(7) Uani 1 1 d D . . . .
C4 C 0.26164(10) 0.5040(5) 0.0116(4) 0.0383(6) Uani 1 1 d . . . . .
H4 H 0.272533 0.666697 0.023246 0.046 Uiso 1 1 calc R U . . .
C5 C 0.21279(11) 0.4419(5) 0.0126(5) 0.0499(8) Uani 1 1 d D . . . .
C6 C 0.1957(2) 0.2397(6) -0.0337(12) 0.070(3) Uani 0.673(13) 1 d D . P A 2
H6 H 0.156046 0.193872 -0.044015 0.084 Uiso 0.673(13) 1 calc R U P A 2
C8 C 0.27860(19) 0.1539(5) -0.0539(13) 0.0557(19) Uani 0.673(13) 1 d D . P A 2
H8 H 0.304167 0.042884 -0.082157 0.067 Uiso 0.673(13) 1 calc R U P A 2
C7 C 0.2281(2) 0.0947(8) -0.0672(15) 0.077(3) Uani 0.673(13) 1 d D . P A 2
H7 H 0.214017 -0.063108 -0.103301 0.092 Uiso 0.673(13) 1 calc R U P A 2
H13 H 0.4647(12) 0.436(5) 0.619(4) 0.032(8) Uiso 1 1 d . . . . .
H12 H 0.4715(14) 0.133(5) 0.788(5) 0.045(9) Uiso 1 1 d . . . . .
C8A C 0.2877(3) 0.1547(6) 0.0386(14) 0.028(2) Uani 0.327(13) 1 d D . P A 1
H8A H 0.318962 0.039339 0.062756 0.034 Uiso 0.327(13) 1 calc R U P A 1
C7A C 0.2403(3) 0.0965(12) 0.0520(14) 0.030(2) Uani 0.327(13) 1 d D . P A 1
H7A H 0.232060 -0.066666 0.060090 0.036 Uiso 0.327(13) 1 calc R U P A 1
C6A C 0.2034(4) 0.2424(6) 0.0553(16) 0.031(2) Uani 0.327(13) 1 d D . P A 1
H6A H 0.169681 0.203500 0.088853 0.037 Uiso 0.327(13) 1 calc R U P A 1


_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
S1 N1 1.695(2) . ?
S1 C1 1.758(2) . ?
Cl1 C5 1.736(3) . ?
O2 C1 1.209(3) . ?
O1 N2 1.384(2) . ?
O1 C9 1.408(3) . ?
N3 C9 1.308(3) . ?
N3 C13 1.358(3) . ?
N2 C1 1.389(3) . ?
N2 C2 1.380(3) . ?
N1 C2 1.286(3) . ?
C9 C10 1.387(3) . ?
C10 H10 1.0850 . ?
C10 C11 1.380(3) . ?
C11 H11 1.0850 . ?
C11 C12 1.386(4) . ?
C2 C3 1.488(3) . ?
C13 C12 1.376(4) . ?
C13 H13 0.97(3) . ?
C12 H12 0.94(4) . ?
C3 C4 1.395(4) . ?
C3 C8 1.3853(10) . ?
C3 C8A 1.3846(10) . ?
C4 H4 1.0850 . ?
C4 C5 1.388(4) . ?
C5 C6 1.3848(10) . ?
C5 C6A 1.384(2) . ?
C6 H6 1.0850 . ?
C6 C7 1.3845(10) . ?
C8 H8 1.0850 . ?
C8 C7 1.3845(10) . ?
C7 H7 1.0850 . ?
C8A H8A 1.0850 . ?
C8A C7A 1.3843(10) . ?
C7A H7A 1.0850 . ?
C7A C6A 1.384(2) . ?
C6A H6A 1.0850 . ?

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
N1 S1 C1 94.79(11) . . ?
N2 O1 C9 112.53(17) . . ?
C9 N3 C13 115.8(2) . . ?
O1 N2 C1 118.27(18) . . ?
C2 N2 O1 123.82(19) . . ?
C2 N2 C1 116.2(2) . . ?
C2 N1 S1 110.30(17) . . ?
N3 C9 O1 118.9(2) . . ?
N3 C9 C10 126.9(2) . . ?
C10 C9 O1 114.2(2) . . ?
C9 C10 H10 122.0 . . ?
C11 C10 C9 116.0(2) . . ?
C11 C10 H10 122.0 . . ?
O2 C1 S1 131.32(19) . . ?
O2 C1 N2 125.3(2) . . ?
N2 C1 S1 103.41(16) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(2) . . ?
C12 C11 H11 120.2 . . ?
N2 C2 C3 122.3(2) . . ?
N1 C2 N2 115.0(2) . . ?
N1 C2 C3 122.7(2) . . ?
N3 C13 C12 122.8(2) . . ?
N3 C13 H13 114.0(18) . . ?
C12 C13 H13 123.1(18) . . ?
C11 C12 H12 123(2) . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12 118(2) . . ?
C4 C3 C2 116.5(2) . . ?
C8 C3 C2 121.8(3) . . ?
C8 C3 C4 120.2(3) . . ?
C8A C3 C2 125.4(3) . . ?
C8A C3 C4 115.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 Cl1 119.4(2) . . ?
C6 C5 Cl1 120.8(3) . . ?
C6 C5 C4 119.1(4) . . ?
C6A C5 Cl1 114.0(3) . . ?
C6A C5 C4 123.0(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(5) . . ?
C7 C6 H6 119.3 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.0(4) . . ?
C7 C8 H8 120.0 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.1(5) . . ?
C8 C7 H7 120.5 . . ?
C3 C8A H8A 118.8 . . ?
C7A C8A C3 122.4(6) . . ?
C7A C8A H8A 118.8 . . ?
C8A C7A H7A 119.4 . . ?
C6A C7A C8A 121.3(7) . . ?
C6A C7A H7A 119.4 . . ?
C5 C6A C7A 114.8(6) . . ?
C5 C6A H6A 122.6 . . ?
C7A C6A H6A 122.6 . . ?

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
S1 N1 C2 N2 -1.5(3) . . . . ?
S1 N1 C2 C3 -179.4(2) . . . . ?
Cl1 C5 C6 C7 175.4(6) . . . . ?
Cl1 C5 C6A C7A -174.3(6) . . . . ?
O1 N2 C1 S1 -171.16(15) . . . . ?
O1 N2 C1 O2 8.6(3) . . . . ?
O1 N2 C2 N1 169.8(2) . . . . ?
O1 N2 C2 C3 -12.3(4) . . . . ?
O1 C9 C10 C11 179.32(19) . . . . ?
N3 C9 C10 C11 -0.3(4) . . . . ?
N3 C13 C12 C11 0.0(4) . . . . ?
N2 O1 C9 N3 -3.9(3) . . . . ?
N2 O1 C9 C10 176.42(19) . . . . ?
N2 C2 C3 C4 159.6(3) . . . . ?
N2 C2 C3 C8 -34.5(6) . . . . ?
N2 C2 C3 C8A -0.2(7) . . . . ?
N1 S1 C1 O2 -176.0(2) . . . . ?
N1 S1 C1 N2 3.73(16) . . . . ?
N1 C2 C3 C4 -22.6(4) . . . . ?
N1 C2 C3 C8 143.3(5) . . . . ?
N1 C2 C3 C8A 177.6(6) . . . . ?
C9 O1 N2 C1 79.9(2) . . . . ?
C9 O1 N2 C2 -84.8(3) . . . . ?
C9 N3 C13 C12 -0.3(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C1 S1 N1 C2 -1.4(2) . . . . ?
C1 N2 C2 N1 4.8(3) . . . . ?
C1 N2 C2 C3 -177.3(2) . . . . ?
C2 N2 C1 S1 -5.3(2) . . . . ?
C2 N2 C1 O2 174.5(2) . . . . ?
C2 C3 C4 C5 178.6(3) . . . . ?
C2 C3 C8 C7 -172.8(6) . . . . ?
C2 C3 C8A C7A 175.6(6) . . . . ?
C13 N3 C9 O1 -179.12(19) . . . . ?
C13 N3 C9 C10 0.5(4) . . . . ?
C3 C4 C5 Cl1 178.4(2) . . . . ?
C3 C4 C5 C6 -11.1(6) . . . . ?
C3 C4 C5 C6A 21.0(7) . . . . ?
C3 C8 C7 C6 1.2(12) . . . . ?
C3 C8A C7A C6A -11.8(14) . . . . ?
C4 C3 C8 C7 -7.4(9) . . . . ?
C4 C3 C8A C7A 15.6(10) . . . . ?
C4 C5 C6 C7 5.1(9) . . . . ?
C4 C5 C6A C7A -15.8(11) . . . . ?
C5 C6 C7 C8 0.0(11) . . . . ?
C8 C3 C4 C5 12.4(6) . . . . ?
C8A C3 C4 C5 -19.6(6) . . . . ?
C8A C7A C6A C5 10.9(13) . . . . ?

_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 2.508
_oxdiff_exptl_absorpt_empirical_full_min 0.438
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_syn-549
_database_code_depnum_ccdc_archive 'CCDC 2474622'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2025-07-21 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_audit_creation_date             2025-06-17
_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        N'-([2,2'-bipyridin]-6-yloxy)benzimidamide
_chemical_formula_moiety         'C17 H14 N4 O'
_chemical_formula_sum            'C17 H14 N4 O'
_chemical_formula_weight         290.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H14 N4 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.1399(3)
_cell_length_b                   6.21410(10)
_cell_length_c                   21.7378(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.6270(10)
_cell_angle_gamma                90
_cell_volume                     2849.88(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6700
_cell_measurement_theta_min      2.0460
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8402
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.816
_diffrn_reflns_theta_min         4.076
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  43.00   0.50    0.20    --   41.10 -86.00  97.00  134
  2  ω    103.00 128.00   0.50    0.80    --  100.00 -86.00  97.00   50
  3  ω     87.00 157.00   0.50    0.80    --  100.00  86.00-145.00  140
  4  ω     37.00  73.00   0.50    0.80    --  100.00 -86.00  97.00   72
  5  ω    -68.00 -36.00   0.50    0.20    --  -41.10  86.00-145.00   64
  6  ω    -11.00  14.00   0.50    0.20    --  -41.10  86.00-145.00   50
  7  ω    -92.00 -22.00   0.50    0.20    --  -41.10 -65.00  90.00  140
  8  ω    -14.00  22.00   0.50    0.20    --  -41.10  54.00 -60.00   72
  9  ω    -54.00 -18.00   0.50    0.20    --  -41.10  54.00 -60.00   72
 10  ω    -11.00  25.00   0.50    0.20    --  -41.10  32.00   0.00   72
 11  ω    -48.00 -16.00   0.50    0.20    --  -41.10  32.00   0.00   64
 12  ω     33.00 107.00   0.50    0.20    --   41.10  32.00-120.00  148
 13  ω     18.00  46.00   0.50    0.20    --   41.10 -65.00 150.00   56
 14  ω    -21.00   4.00   0.50    0.20    --   41.10 -65.00 150.00   50
 15  ω     37.00  62.00   0.50    0.20    --   41.10  11.00 -30.00   50
 16  ω     22.00  48.00   0.50    0.20    --   41.10 -21.00  90.00   52
 17  ω    -11.00  31.00   0.50    0.20    --   41.10 -43.00  90.00   84
 18  ω     68.00  93.00   0.50    0.20    --   41.10  11.00 -30.00   50
 19  ω    -17.00   8.00   0.50    0.20    --   41.10 -21.00  90.00   50
 20  ω     87.00 130.00   0.50    0.80    --  100.00  93.00 150.00   86
 21  ω     87.00 136.00   0.50    0.80    --  100.00   8.00   0.00   98
 22  ω     37.00  83.00   0.50    0.80    --  100.00 -59.00 -60.00   92
 23  ω     31.00  69.00   0.50    0.80    --  100.00 -93.00-180.00   76
 24  ω    104.00 155.00   0.50    0.80    --  100.00 111.00 150.00  102
 25  ω     82.00 108.00   0.50    0.80    --  100.00 -42.00  60.00   52
 26  ω     84.00 143.00   0.50    0.80    --  100.00  50.00 150.00  118
 27  ω    132.00 157.00   0.50    0.80    --  100.00  68.00-150.00   50
 28  ω    108.00 157.00   0.50    0.80    --  100.00  77.00-120.00   98
 29  ω     80.00 107.00   0.50    0.80    --  100.00  68.00-150.00   54
 30  ω     38.00 103.00   0.50    0.80    --  100.00-133.00 -90.00  130
 31  ω    126.00 152.00   0.50    0.80    --  100.00  77.00   0.00   52
 32  ω     38.00  67.00   0.50    0.80    --  100.00 -42.00  60.00   58
 33  ω     74.00 108.00   0.50    0.80    --  100.00 -54.00  49.58   68
 34  ω     29.00 113.00   0.50    0.80    --  100.00 -17.00-120.00  168
 35  ω     76.00 102.00   0.50    0.80    --  100.00-111.00-180.00   52
 36  ω    112.00 137.00   0.50    0.80    --  100.00  33.00 120.00   50
 37  ω     39.00  97.00   0.50    0.80    --  100.00-133.00-180.00  116
 38  ω    101.00 126.00   0.50    0.80    --  100.00  33.00-120.00   50
 39  ω     83.00 157.00   0.50    0.80    --  100.00  77.00-180.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319247000
_diffrn_orient_matrix_UB_12      -0.2021459000
_diffrn_orient_matrix_UB_13      -0.0249247000
_diffrn_orient_matrix_UB_21      0.0654970000
_diffrn_orient_matrix_UB_22      0.0901155000
_diffrn_orient_matrix_UB_23      0.0219437000
_diffrn_orient_matrix_UB_31      -0.0050075000
_diffrn_orient_matrix_UB_32      -0.1115715000
_diffrn_orient_matrix_UB_33      0.0627689000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2602
_reflns_number_total             2791
_reflns_odcompleteness_completeness 94.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_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         0.193
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.068
_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)+(0.0659P)²+1.8283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1161
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C10(H10), C4(H4), C11(H11), C9(H9), C17(H17), C15(H15),
 C16(H16), C6(H6), C14(H14), C5(H5)
;
_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 0.29789(4) 0.50476(14) 0.54707(4) 0.0227(2) Uani 1 1 d . . . . .
N3 N 0.37414(5) 0.47436(17) 0.48180(5) 0.0182(2) Uani 1 1 d . . . . .
N4 N 0.42390(5) 0.65263(17) 0.38040(5) 0.0201(2) Uani 1 1 d . . . . .
N2 N 0.21313(5) 0.73293(17) 0.59535(5) 0.0209(2) Uani 1 1 d . . . . .
N1 N 0.27268(5) 0.40910(18) 0.60143(5) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.19944(5) 0.47369(19) 0.67689(6) 0.0180(3) Uani 1 1 d . . . . .
C8 C 0.33940(5) 0.3701(2) 0.52057(5) 0.0187(3) Uani 1 1 d . . . . .
C12 C 0.41819(5) 0.3627(2) 0.45327(5) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.23002(5) 0.5396(2) 0.61995(6) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.45509(6) 0.48942(19) 0.40961(6) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.17242(6) 0.2696(2) 0.68167(6) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.173881 0.156093 0.643862 0.024 Uiso 1 1 calc R U . . .
C3 C 0.19801(5) 0.6178(2) 0.72594(6) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.218166 0.777397 0.721894 0.023 Uiso 1 1 calc R U . . .
C10 C 0.38899(6) 0.0366(2) 0.50229(6) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.394170 -0.135542 0.509262 0.027 Uiso 1 1 calc R U . . .
C4 C 0.17089(6) 0.5581(2) 0.78000(6) 0.0218(3) Uani 1 1 d . . . . .
H4 H 0.171228 0.668767 0.818627 0.026 Uiso 1 1 calc R U . . .
C11 C 0.42803(6) 0.1435(2) 0.46302(6) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.465050 0.058276 0.440650 0.026 Uiso 1 1 calc R U . . .
C9 C 0.34367(6) 0.1487(2) 0.53245(6) 0.0209(3) Uani 1 1 d . . . . .
H9 H 0.313048 0.069473 0.563654 0.025 Uiso 1 1 calc R U . . .
C17 C 0.45588(6) 0.7739(2) 0.34206(6) 0.0221(3) Uani 1 1 d . . . . .
H17 H 0.430889 0.904571 0.317969 0.026 Uiso 1 1 calc R U . . .
C15 C 0.55107(6) 0.5729(2) 0.36157(6) 0.0244(3) Uani 1 1 d . . . . .
H15 H 0.600641 0.542540 0.354557 0.029 Uiso 1 1 calc R U . . .
C16 C 0.51937(6) 0.7419(2) 0.33137(6) 0.0236(3) Uani 1 1 d . . . . .
H16 H 0.543437 0.846041 0.300308 0.028 Uiso 1 1 calc R U . . .
C6 C 0.14360(6) 0.2126(2) 0.73519(6) 0.0223(3) Uani 1 1 d . . . . .
H6 H 0.121319 0.056142 0.738536 0.027 Uiso 1 1 calc R U . . .
C14 C 0.51855(6) 0.4438(2) 0.40076(6) 0.0229(3) Uani 1 1 d . . . . .
H14 H 0.542042 0.308944 0.424260 0.028 Uiso 1 1 calc R U . . .
C5 C 0.14330(6) 0.3557(2) 0.78437(6) 0.0236(3) Uani 1 1 d . . . . .
H5 H 0.121499 0.309466 0.826257 0.028 Uiso 1 1 calc R U . . .
H2A H 0.2289(8) 0.765(3) 0.5576(8) 0.029(4) Uiso 1 1 d . . . . .
H2B H 0.1731(9) 0.778(3) 0.6033(8) 0.031(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 N1 1.4537(13) . ?
O1 C8 1.3663(15) . ?
N3 C8 1.3220(16) . ?
N3 C12 1.3439(15) . ?
N4 C13 1.3467(16) . ?
N4 C17 1.3385(16) . ?
N2 C1 1.3537(16) . ?
N2 H2A 0.925(18) . ?
N2 H2B 0.918(19) . ?
N1 C1 1.2958(16) . ?
C2 C1 1.4895(17) . ?
C2 C7 1.3974(17) . ?
C2 C3 1.3943(18) . ?
C8 C9 1.4015(18) . ?
C12 C13 1.4908(17) . ?
C12 C11 1.3925(18) . ?
C13 C14 1.3965(17) . ?
C7 H7 1.0850 . ?
C7 C6 1.3929(18) . ?
C3 H3 1.0850 . ?
C3 C4 1.3903(18) . ?
C10 H10 1.0850 . ?
C10 C11 1.3928(19) . ?
C10 C9 1.3828(18) . ?
C4 H4 1.0850 . ?
C4 C5 1.3921(19) . ?
C11 H11 1.0850 . ?
C9 H9 1.0850 . ?
C17 H17 1.0850 . ?
C17 C16 1.3907(18) . ?
C15 H15 1.0850 . ?
C15 C16 1.3880(19) . ?
C15 C14 1.3845(19) . ?
C16 H16 1.0850 . ?
C6 H6 1.0850 . ?
C6 C5 1.3907(19) . ?
C14 H14 1.0850 . ?
C5 H5 1.0850 . ?

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
C8 O1 N1 111.75(9) . . ?
C8 N3 C12 118.05(11) . . ?
C17 N4 C13 117.79(10) . . ?
C1 N2 H2A 115.9(11) . . ?
C1 N2 H2B 114.9(11) . . ?
H2A N2 H2B 119.3(16) . . ?
C1 N1 O1 107.14(10) . . ?
C7 C2 C1 120.82(11) . . ?
C3 C2 C1 119.36(11) . . ?
C3 C2 C7 119.82(12) . . ?
O1 C8 C9 124.00(11) . . ?
N3 C8 O1 111.47(10) . . ?
N3 C8 C9 124.52(11) . . ?
N3 C12 C13 115.27(11) . . ?
N3 C12 C11 122.41(11) . . ?
C11 C12 C13 122.31(11) . . ?
N2 C1 C2 117.05(11) . . ?
N1 C1 N2 127.17(12) . . ?
N1 C1 C2 115.67(11) . . ?
N4 C13 C12 115.95(10) . . ?
N4 C13 C14 122.28(12) . . ?
C14 C13 C12 121.75(11) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 C2 119.69(12) . . ?
C6 C7 H7 120.2 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.33(12) . . ?
C4 C3 H3 119.8 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.37(12) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.72(12) . . ?
C5 C4 H4 120.1 . . ?
C12 C11 C10 118.11(11) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C8 C9 H9 121.8 . . ?
C10 C9 C8 116.46(12) . . ?
C10 C9 H9 121.8 . . ?
N4 C17 H17 118.2 . . ?
N4 C17 C16 123.65(12) . . ?
C16 C17 H17 118.2 . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.07(11) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 C17 118.13(12) . . ?
C15 C16 H16 120.9 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.20(12) . . ?
C5 C6 H6 119.9 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.06(12) . . ?
C15 C14 H14 120.5 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.19(12) . . ?
C6 C5 H5 119.9 . . ?

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 N1 C1 N2 -2.28(17) . . . . ?
O1 N1 C1 C2 -178.21(9) . . . . ?
O1 C8 C9 C10 -179.12(11) . . . . ?
N3 C8 C9 C10 1.95(18) . . . . ?
N3 C12 C13 N4 -31.83(15) . . . . ?
N3 C12 C13 C14 146.82(11) . . . . ?
N3 C12 C11 C10 2.22(18) . . . . ?
N4 C13 C14 C15 1.31(19) . . . . ?
N4 C17 C16 C15 0.86(19) . . . . ?
N1 O1 C8 N3 -163.77(9) . . . . ?
N1 O1 C8 C9 17.18(16) . . . . ?
C2 C7 C6 C5 -1.85(18) . . . . ?
C2 C3 C4 C5 -2.00(18) . . . . ?
C8 O1 N1 C1 -174.50(10) . . . . ?
C8 N3 C12 C13 179.25(10) . . . . ?
C8 N3 C12 C11 0.24(17) . . . . ?
C12 N3 C8 O1 178.54(10) . . . . ?
C12 N3 C8 C9 -2.41(18) . . . . ?
C12 C13 C14 C15 -177.26(11) . . . . ?
C1 C2 C7 C6 -179.41(11) . . . . ?
C1 C2 C3 C4 -178.66(11) . . . . ?
C13 N4 C17 C16 -0.69(18) . . . . ?
C13 C12 C11 C10 -176.73(11) . . . . ?
C7 C2 C1 N2 131.11(12) . . . . ?
C7 C2 C1 N1 -52.53(15) . . . . ?
C7 C2 C3 C4 1.20(17) . . . . ?
C7 C6 C5 C4 1.06(18) . . . . ?
C3 C2 C1 N2 -49.02(15) . . . . ?
C3 C2 C1 N1 127.33(12) . . . . ?
C3 C2 C7 C6 0.72(17) . . . . ?
C3 C4 C5 C6 0.87(18) . . . . ?
C11 C12 C13 N4 147.19(12) . . . . ?
C11 C12 C13 C14 -34.16(18) . . . . ?
C11 C10 C9 C8 0.68(18) . . . . ?
C9 C10 C11 C12 -2.62(18) . . . . ?
C17 N4 C13 C12 178.24(10) . . . . ?
C17 N4 C13 C14 -0.41(18) . . . . ?
C16 C15 C14 C13 -1.10(19) . . . . ?
C14 C15 C16 C17 0.08(19) . . . . ?

_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 1.931
_oxdiff_exptl_absorpt_empirical_full_min 0.626
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_syn-557
_database_code_depnum_ccdc_archive 'CCDC 2474623'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2025-07-21 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_audit_creation_date             2025-06-17
_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        
N'-((3,5-dimethylpyridin-2-yl)oxy)benzimidamide
_chemical_formula_moiety         'C14 H15 N3 O'
_chemical_formula_sum            'C14 H15 N3 O'
_chemical_formula_weight         241.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H15 N3 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   10.23780(10)
_cell_length_b                   10.23780(10)
_cell_length_c                   10.7057(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     971.76(3)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    4957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6820
_cell_measurement_theta_min      4.1280
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5945
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.528
_diffrn_reflns_theta_min         4.988
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00 -33.00   0.50    0.25    --  -41.10 111.00 -49.00   84
  2  ω    -29.00  -1.00   0.50    0.25    --  -41.10 111.00 -49.00   56
  3  ω     39.00  95.00   0.50    1.00    --  100.00 -36.00 -61.00  112
  4  ω     73.00 118.00   0.50    1.00    --  100.00 -74.00 101.00   90
  5  ω     37.00  79.00   0.50    1.00    --  100.00 -64.00 -63.00   84
  6  ω    113.00 146.00   0.50    1.00    --  100.00  17.00 141.00   66
  7  ω    -75.00 -31.00   0.50    0.25    --  -41.10 -21.00 -30.00   88
  8  ω     33.00  59.00   0.50    0.25    --   41.10  43.00-120.00   52
  9  ω      5.00  51.00   0.50    0.25    --   41.10 -43.00   0.00   92
 10  ω     39.00  65.00   0.50    0.25    --   41.10 -11.00 150.00   52
 11  ω     63.00  97.00   0.50    0.25    --   41.10  43.00-120.00   68
 12  ω    -22.00   3.00   0.50    0.25    --   41.10 -11.00 150.00   50
 13  ω     94.00 142.00   0.50    1.00    --  100.00  42.00-180.00   96
 14  ω    118.00 151.00   0.50    1.00    --  100.00  33.00  30.00   66
 15  ω    131.00 156.00   0.50    1.00    --  100.00 111.00-180.00   50
 16  ω    109.00 157.00   0.50    1.00    --  100.00  17.00 -30.00   96
 17  ω     60.00 109.00   0.50    1.00    --  100.00 -25.00 -60.00   98
 18  ω     91.00 127.00   0.50    1.00    --  100.00  25.00-180.00   72
 19  ω     32.00  96.00   0.50    1.00    --  100.00 -25.00-120.00  128
 20  ω     97.00 153.00   0.50    1.00    --  100.00  36.00  95.00  112
 21  ω     82.00 118.00   0.50    1.00    --  100.00 122.00-146.00   72
 22  ω   -100.00 -70.00   0.50    0.25    --  -41.10 -43.00-180.00   60
 23  ω    -58.00 -32.00   0.50    0.25    --  -41.10 -43.00-180.00   52
 24  ω     37.00  67.00   0.50    0.25    --   41.10 -77.00-150.00   60
 25  ω     82.00 107.00   0.50    0.25    --   41.10  32.00-120.00   50
 26  ω    -15.00  23.00   0.50    0.25    --   41.10 -77.00-150.00   76
 27  ω     41.00  69.00   0.50    1.00    --  100.00 -68.00 -30.00   56
 28  ω    112.00 157.00   0.50    1.00    --  100.00  93.00 -30.00   90
 29  ω     67.00 114.00   0.50    1.00    --  100.00 -50.00 -30.00   94
 30  ω    123.00 157.00   0.50    1.00    --  100.00  42.00  60.00   68
 31  ω     36.00  77.00   0.50    1.00    --  100.00 -68.00  90.00   82
 32  ω     87.00 113.00   0.50    1.00    --  100.00  42.00  60.00   52
 33  ω     78.00 117.00   0.50    1.00    --  100.00-133.00   0.00   78
 34  ω     82.00 107.00   0.50    1.00    --  100.00-111.00 150.00   50
 35  ω     92.00 118.00   0.50    1.00    --  100.00 -68.00 -30.00   52
 36  ω     38.00  92.00   0.50    1.00    --  100.00 -68.00 150.00  108
 37  ω     52.00  97.00   0.50    1.00    --  100.00 -93.00-150.00   90
 38  ω     37.00  99.00   0.50    1.00    --  100.00 -50.00-180.00  124
 39  ω     56.00  98.00   0.50    1.00    --  100.00 -93.00-120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0216788000
_diffrn_orient_matrix_UB_12      0.1592499000
_diffrn_orient_matrix_UB_13      -0.0159031000
_diffrn_orient_matrix_UB_21      0.0323229000
_diffrn_orient_matrix_UB_22      -0.0038016000
_diffrn_orient_matrix_UB_23      -0.1400729000
_diffrn_orient_matrix_UB_31      -0.1693367000
_diffrn_orient_matrix_UB_32      -0.0695254000
_diffrn_orient_matrix_UB_33      -0.0287406000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                2347
_reflns_number_total             2387
_reflns_odcompleteness_completeness 97.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_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         0.165
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1071 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.054
_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)+(0.0488P)²+0.1567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C12(H12), C5(H5), C6(H6), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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 0.55445(16) 1.01315(16) 0.43546(14) 0.0220(3) Uani 1 1 d . . . . .
N2 N 0.2851(2) 0.8911(2) 0.36014(19) 0.0245(4) Uani 1 1 d . . . . .
H2A H 0.190630 0.807438 0.318389 0.029 Uiso 1 1 d R U . . .
N1 N 0.4506(2) 0.8892(2) 0.51399(17) 0.0221(4) Uani 1 1 d . . . . .
N3 N 0.7430(2) 0.9793(2) 0.52703(17) 0.0243(4) Uani 1 1 d . . . . .
C1 C 0.3175(2) 0.8360(2) 0.4639(2) 0.0208(4) Uani 1 1 d . . . . .
C8 C 0.7035(2) 1.0614(2) 0.45945(19) 0.0193(4) Uani 1 1 d . . . . .
C9 C 0.8042(2) 1.1998(2) 0.40224(19) 0.0206(4) Uani 1 1 d . . . . .
C7 C 0.2225(2) 0.6176(2) 0.6095(2) 0.0252(4) Uani 1 1 d . . . . .
H7 H 0.337750 0.641447 0.620486 0.030 Uiso 1 1 calc R U . . .
C2 C 0.1920(2) 0.7069(2) 0.53041(19) 0.0219(4) Uani 1 1 d . . . . .
C10 C 0.9554(2) 1.2491(2) 0.4184(2) 0.0229(4) Uani 1 1 d . . . . .
H10 H 1.038652 1.355463 0.377350 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8929(2) 1.0327(2) 0.5398(2) 0.0256(5) Uani 1 1 d . . . . .
H12 H 0.928232 0.967251 0.595365 0.031 Uiso 1 1 calc R U . . .
C11 C 1.0034(3) 1.1644(3) 0.4869(2) 0.0248(5) Uani 1 1 d . . . . .
C5 C -0.0408(2) 0.4661(3) 0.6598(2) 0.0290(5) Uani 1 1 d . . . . .
H5 H -0.131367 0.372737 0.710045 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1071(3) 0.4981(3) 0.6747(2) 0.0280(5) Uani 1 1 d . . . . .
H6 H 0.132491 0.430121 0.737017 0.034 Uiso 1 1 calc R U . . .
C3 C 0.0431(2) 0.6744(3) 0.5157(2) 0.0269(5) Uani 1 1 d . . . . .
H3 H 0.017406 0.742827 0.454131 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7473(3) 1.2832(3) 0.3257(2) 0.0302(5) Uani 1 1 d . . . . .
H13A H 0.700217 1.222726 0.238008 0.045 Uiso 1 1 calc R U . . .
H13B H 0.840484 1.396718 0.305394 0.045 Uiso 1 1 calc R U . . .
H13C H 0.659509 1.291343 0.377737 0.045 Uiso 1 1 calc R U . . .
C4 C -0.0722(3) 0.5539(3) 0.5803(2) 0.0312(5) Uani 1 1 d . . . . .
H4 H -0.187903 0.528351 0.568382 0.037 Uiso 1 1 calc R U . . .
C14 C 1.1685(3) 1.2156(3) 0.5031(3) 0.0343(6) Uani 1 1 d . . . . .
H14A H 1.219010 1.221064 0.411711 0.051 Uiso 1 1 calc R U . . .
H14B H 1.180564 1.135421 0.562878 0.051 Uiso 1 1 calc R U . . .
H14C H 1.225857 1.327412 0.546543 0.051 Uiso 1 1 calc R U . . .
H2B H 0.363(3) 0.961(3) 0.319(3) 0.025(6) 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 N1 1.449(2) . ?
O1 C8 1.373(2) . ?
N2 H2A 1.0200 . ?
N2 C1 1.359(3) . ?
N2 H2B 0.88(3) . ?
N1 C1 1.304(3) . ?
N3 C8 1.317(3) . ?
N3 C12 1.354(3) . ?
C1 C2 1.486(3) . ?
C8 C9 1.408(3) . ?
C9 C10 1.379(3) . ?
C9 C13 1.496(3) . ?
C7 H7 1.0850 . ?
C7 C2 1.392(3) . ?
C7 C6 1.391(3) . ?
C2 C3 1.397(3) . ?
C10 H10 1.0850 . ?
C10 C11 1.399(3) . ?
C12 H12 1.0850 . ?
C12 C11 1.376(3) . ?
C11 C14 1.509(3) . ?
C5 H5 1.0850 . ?
C5 C6 1.389(3) . ?
C5 C4 1.388(4) . ?
C6 H6 1.0850 . ?
C3 H3 1.0850 . ?
C3 C4 1.392(3) . ?
C13 H13A 1.0950 . ?
C13 H13B 1.0950 . ?
C13 H13C 1.0950 . ?
C4 H4 1.0850 . ?
C14 H14A 1.0950 . ?
C14 H14B 1.0950 . ?
C14 H14C 1.0950 . ?

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
C8 O1 N1 113.80(14) . . ?
H2A N2 H2B 124.2 . . ?
C1 N2 H2A 109.6 . . ?
C1 N2 H2B 115.7(18) . . ?
C1 N1 O1 106.43(16) . . ?
C8 N3 C12 116.42(18) . . ?
N2 C1 C2 118.61(19) . . ?
N1 C1 N2 125.73(19) . . ?
N1 C1 C2 115.64(18) . . ?
O1 C8 C9 113.79(17) . . ?
N3 C8 O1 120.91(17) . . ?
N3 C8 C9 125.26(19) . . ?
C8 C9 C13 120.97(18) . . ?
C10 C9 C8 115.90(19) . . ?
C10 C9 C13 123.10(19) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C2 120.8(2) . . ?
C7 C2 C1 119.86(18) . . ?
C7 C2 C3 119.3(2) . . ?
C3 C2 C1 120.87(19) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
N3 C12 H12 117.8 . . ?
N3 C12 C11 124.4(2) . . ?
C11 C12 H12 117.8 . . ?
C10 C11 C14 121.7(2) . . ?
C12 C11 C10 116.8(2) . . ?
C12 C11 C14 121.5(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 H6 120.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 N1 C1 N2 -1.6(3) . . . . ?
O1 N1 C1 C2 -179.71(16) . . . . ?
O1 C8 C9 C10 -176.84(18) . . . . ?
O1 C8 C9 C13 1.3(3) . . . . ?
N2 C1 C2 C7 159.37(19) . . . . ?
N2 C1 C2 C3 -21.3(3) . . . . ?
N1 O1 C8 N3 14.3(3) . . . . ?
N1 O1 C8 C9 -167.74(16) . . . . ?
N1 C1 C2 C7 -22.4(3) . . . . ?
N1 C1 C2 C3 157.01(19) . . . . ?
N3 C8 C9 C10 1.0(3) . . . . ?
N3 C8 C9 C13 179.1(2) . . . . ?
N3 C12 C11 C10 1.7(3) . . . . ?
N3 C12 C11 C14 -178.8(2) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C8 O1 N1 C1 -166.98(17) . . . . ?
C8 N3 C12 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C9 C10 C11 C14 178.7(2) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C2 C7 C6 C5 0.8(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C12 N3 C8 O1 176.55(19) . . . . ?
C12 N3 C8 C9 -1.1(3) . . . . ?
C6 C7 C2 C1 178.7(2) . . . . ?
C6 C7 C2 C3 -0.7(3) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C13 C9 C10 C11 -177.5(2) . . . . ?
C4 C5 C6 C7 -0.3(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 2.300
_oxdiff_exptl_absorpt_empirical_full_min 0.580
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
