# 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_amine_3jb_auto
_database_code_depnum_ccdc_archive 'CCDC 2389333'
loop_
_audit_author_name
_audit_author_address
'Maureen Gumbo'
;Chalmers University of Technology
Sweden
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2025-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H16 N6 O'
_chemical_formula_sum            'C12 H16 N6 O'
_chemical_formula_weight         260.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5086(3)
_cell_length_b                   6.6541(2)
_cell_length_c                   10.6871(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.228(4)
_cell_angle_gamma                90
_cell_volume                     625.94(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4122
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4650
_cell_measurement_theta_min      4.4440
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.130a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0245
-1 0 0 0.0279
-1 -2 2 0.0788
1 2 -2 0.0991
1 0 2 0.0267
0 0 1 0.0239
0 0 -1 0.0080

_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.032
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9991 0.0008 -0.0004 0.0239 0.1112 0.1328
-0.9991 -0.0008 0.0004 -0.0239 -0.1112 -0.1328
-0.9983 -1.9972 2.0057 -0.0865 -0.4429 0.3113
0.9983 1.9972 -2.0057 0.0865 0.4429 -0.3113
0.9996 0.0027 2.0018 -0.2220 0.1210 0.3236
0.0003 0.0010 1.0011 -0.1230 0.0049 0.0954
-0.0003 -0.0010 -1.0011 0.1230 -0.0049 -0.0954

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6417
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.595
_diffrn_reflns_theta_min         4.469
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     95.00 178.00   0.50    0.46    --  108.56  45.00  90.00  166
  2  ω     30.00 121.00   0.50    0.11    --   43.25  38.00  60.00  182
  3  ω     34.00  79.00   0.50    0.46    --  108.56 -77.00  55.00   90
  4  ω     34.00  79.00   0.50    0.46    --  108.56 -77.00 -30.00   90
  5  ω    109.00 178.00   0.50    0.46    --  108.56  77.00-178.00  138
  6  ω     34.00  79.00   0.50    0.46    --  108.56 -77.00-120.00   90
  7  ω    -30.00  49.00   0.50    0.11    --   43.25 -57.00 -90.00  158
  8  ω    -30.00  49.00   0.50    0.11    --   43.25 -57.00 -90.00  158
  9  ω    -66.00  21.00   0.50    0.11    --  -43.25  77.00-178.00  174
 10  ω    -15.00  34.00   0.50    0.11    --  -43.25  38.00 -90.00   98
 11  ω    -14.00  66.00   0.50    0.11    --   43.25 -77.00  55.00  160
 12  ω     35.00  93.00   0.50    0.46    --  108.56 -94.00  90.00  116
 13  ω    -15.00  34.00   0.50    0.11    --  -43.25  38.00-120.00   98
 14  ω    -72.00 -30.00   0.50    0.46    -- -104.50  77.00-178.00   84
 15  ω    -72.00 -30.00   0.50    0.46    -- -104.50  77.00 -90.00   84
 16  ω    -72.00 -30.00   0.50    0.46    -- -104.50  77.00 120.00   84
 17  ω    -72.00 -30.00   0.50    0.46    -- -104.50  77.00 150.00   84
 18  ω   -120.00 -29.00   0.50    0.11    --  -43.25 -38.00   0.00  182
 19  ω   -120.00 -29.00   0.50    0.11    --  -43.25 -38.00-180.00  182
 20  ω   -120.00 -29.00   0.50    0.11    --  -43.25 -38.00 -90.00  182
 21  ω   -120.00 -29.00   0.50    0.11    --  -43.25 -38.00 120.00  182
 22  ω   -132.00 -89.00   0.50    0.46    -- -104.50 -15.00 120.00   86
 23  ω   -132.00 -89.00   0.50    0.46    -- -104.50 -15.00  90.00   86
 24  ω   -174.00-103.00   0.50    0.46    -- -104.50 -77.00  55.00  142
 25  ω   -132.00 -89.00   0.50    0.46    -- -104.50 -15.00 -30.00   86
 26  ω   -163.00 -90.00   0.50    0.46    -- -104.50 -30.00 -30.00  146
 27  ω   -163.00 -90.00   0.50    0.46    -- -104.50 -30.00 -30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0239823000
_diffrn_orient_matrix_UB_12      -0.0919369000
_diffrn_orient_matrix_UB_13      -0.1227602000
_diffrn_orient_matrix_UB_21      0.1112158000
_diffrn_orient_matrix_UB_22      0.1708705000
_diffrn_orient_matrix_UB_23      0.0046642000
_diffrn_orient_matrix_UB_31      0.1330151000
_diffrn_orient_matrix_UB_32      -0.1265250000
_diffrn_orient_matrix_UB_33      0.0954139000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                2006
_reflns_number_total             2208
_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 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.130a 64-bit (release 05-07-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_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 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.1(4)
_refine_ls_extinction_coef       0.0072(17)
_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   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.060
_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)+(0.0555P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0936
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -0.1(4)
 1.1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C00E(H00F)
3.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00C(H00C,H00D), C00H(H00I,H00J), C00I(H00K,H00L), C00J(H00M,
 H00N)
3.c Aromatic/amide H refined with riding coordinates:
 C00F(H00G)
3.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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
O001 O 0.3862(2) 0.7420(3) 0.31435(18) 0.0582(5) Uani 1 1 d . . . . .
H001 H 0.369520 0.651394 0.358907 0.087 Uiso 1 1 calc R U . . .
N002 N 0.3288(2) 0.4252(3) 0.4563(2) 0.0493(5) Uani 1 1 d . . . . .
H002 H 0.399(3) 0.406(5) 0.535(3) 0.059 Uiso 1 1 d . U . . .
N003 N 0.4039(2) 0.3002(3) 0.2141(2) 0.0473(5) Uani 1 1 d . . . . .
N004 N 0.8181(3) 0.8689(4) 0.1235(3) 0.0612(7) Uani 1 1 d . . . . .
N005 N 0.9296(3) 0.5594(4) 0.1010(2) 0.0582(6) Uani 1 1 d . . . . .
C006 C 0.4532(3) 0.4817(4) 0.1901(2) 0.0405(5) Uani 1 1 d . . . . .
C007 C 0.7031(3) 0.5593(4) 0.1495(2) 0.0417(5) Uani 1 1 d . . . . .
N008 N 0.6142(3) 0.2368(4) 0.1940(3) 0.0668(7) Uani 1 1 d . . . . .
C009 C 0.5893(3) 0.4386(4) 0.1772(2) 0.0454(5) Uani 1 1 d . . . . .
N00A N 0.5011(3) 0.1546(4) 0.2164(3) 0.0686(7) Uani 1 1 d . . . . .
C00B C 0.3653(3) 0.6695(4) 0.1847(2) 0.0459(5) Uani 1 1 d . . . . .
H00A H 0.396915 0.771940 0.136223 0.055 Uiso 1 1 calc R U . . .
H00B H 0.258194 0.643376 0.135010 0.055 Uiso 1 1 calc R U . . .
C00C C 0.2677(3) 0.2464(4) 0.2400(2) 0.0495(5) Uani 1 1 d . . . . .
H00C H 0.228159 0.119771 0.195624 0.059 Uiso 1 1 calc R U . . .
H00D H 0.190536 0.348246 0.200953 0.059 Uiso 1 1 calc R U . . .
C00D C 0.7096(3) 0.7673(4) 0.1482(3) 0.0551(7) Uani 1 1 d . . . . .
C00E C 0.2990(3) 0.2271(4) 0.3896(3) 0.0510(6) Uani 1 1 d . . . . .
H00F H 0.386325 0.138357 0.432576 0.061 Uiso 1 1 calc R U . . .
C00F C 0.9220(3) 0.7587(5) 0.1019(3) 0.0577(7) Uani 1 1 d . . . . .
H00G H 0.998150 0.828114 0.085519 0.069 Uiso 1 1 calc R U . . .
C00G C 0.8202(3) 0.4631(5) 0.1249(3) 0.0506(6) Uani 1 1 d . . . . .
C00H C 0.1865(3) 0.4881(5) 0.4691(3) 0.0633(7) Uani 1 1 d . . . . .
H00I H 0.126297 0.569241 0.391998 0.076 Uiso 1 1 calc R U . . .
H00J H 0.208096 0.566976 0.550608 0.076 Uiso 1 1 calc R U . . .
C00I C 0.1017(4) 0.2992(6) 0.4752(4) 0.0776(10) Uani 1 1 d . . . . .
H00K H 0.121148 0.263473 0.568258 0.093 Uiso 1 1 calc R U . . .
H00L H -0.006769 0.317782 0.427664 0.093 Uiso 1 1 calc R U . . .
C00J C 0.1583(4) 0.1419(6) 0.4100(4) 0.0824(10) Uani 1 1 d . . . . .
H00M H 0.080567 0.105624 0.323561 0.099 Uiso 1 1 calc R U . . .
H00N H 0.185541 0.022939 0.466515 0.099 Uiso 1 1 calc R U . . .
H00E H 0.640(3) 0.844(5) 0.171(3) 0.059(8) Uiso 1 1 d . . . . .
H00H H 0.821(3) 0.324(5) 0.124(3) 0.052(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
O001 H001 0.8200 . ?
O001 C00B 1.409(3) . ?
N002 H002 0.86(3) . ?
N002 C00E 1.474(3) . ?
N002 C00H 1.471(3) . ?
N003 C006 1.355(3) . ?
N003 N00A 1.333(3) . ?
N003 C00C 1.467(3) . ?
N004 C00D 1.341(3) . ?
N004 C00F 1.318(4) . ?
N005 C00F 1.328(4) . ?
N005 C00G 1.327(4) . ?
C006 C009 1.383(3) . ?
C006 C00B 1.492(3) . ?
C007 C009 1.466(3) . ?
C007 C00D 1.385(3) . ?
C007 C00G 1.392(3) . ?
N008 C009 1.363(4) . ?
N008 N00A 1.306(3) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00C H00C 0.9700 . ?
C00C H00D 0.9700 . ?
C00C C00E 1.517(3) . ?
C00D H00E 0.94(3) . ?
C00E H00F 0.9800 . ?
C00E C00J 1.543(4) . ?
C00F H00G 0.9300 . ?
C00G H00H 0.92(4) . ?
C00H H00I 0.9700 . ?
C00H H00J 0.9700 . ?
C00H C00I 1.508(5) . ?
C00I H00K 0.9700 . ?
C00I H00L 0.9700 . ?
C00I C00J 1.467(5) . ?
C00J H00M 0.9700 . ?
C00J H00N 0.9700 . ?

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
C00B O001 H001 109.5 . . ?
C00E N002 H002 106(2) . . ?
C00H N002 H002 110.7(19) . . ?
C00H N002 C00E 106.5(2) . . ?
C006 N003 C00C 130.3(2) . . ?
N00A N003 C006 111.4(2) . . ?
N00A N003 C00C 118.3(2) . . ?
C00F N004 C00D 115.9(3) . . ?
C00G N005 C00F 115.6(3) . . ?
N003 C006 C009 103.8(2) . . ?
N003 C006 C00B 121.7(2) . . ?
C009 C006 C00B 134.5(2) . . ?
C00D C007 C009 126.1(2) . . ?
C00D C007 C00G 114.6(2) . . ?
C00G C007 C009 119.3(2) . . ?
N00A N008 C009 108.8(2) . . ?
C006 C009 C007 134.2(2) . . ?
N008 C009 C006 108.3(2) . . ?
N008 C009 C007 117.5(2) . . ?
N008 N00A N003 107.8(2) . . ?
O001 C00B C006 112.35(18) . . ?
O001 C00B H00A 109.1 . . ?
O001 C00B H00B 109.1 . . ?
C006 C00B H00A 109.1 . . ?
C006 C00B H00B 109.1 . . ?
H00A C00B H00B 107.9 . . ?
N003 C00C H00C 109.1 . . ?
N003 C00C H00D 109.1 . . ?
N003 C00C C00E 112.6(2) . . ?
H00C C00C H00D 107.8 . . ?
C00E C00C H00C 109.1 . . ?
C00E C00C H00D 109.1 . . ?
N004 C00D C007 123.1(2) . . ?
N004 C00D H00E 117(2) . . ?
C007 C00D H00E 120(2) . . ?
N002 C00E C00C 111.1(2) . . ?
N002 C00E H00F 109.8 . . ?
N002 C00E C00J 106.1(2) . . ?
C00C C00E H00F 109.8 . . ?
C00C C00E C00J 110.2(2) . . ?
C00J C00E H00F 109.8 . . ?
N004 C00F N005 127.1(3) . . ?
N004 C00F H00G 116.5 . . ?
N005 C00F H00G 116.5 . . ?
N005 C00G C007 123.7(3) . . ?
N005 C00G H00H 117.6(17) . . ?
C007 C00G H00H 118.6(17) . . ?
N002 C00H H00I 110.3 . . ?
N002 C00H H00J 110.3 . . ?
N002 C00H C00I 107.0(3) . . ?
H00I C00H H00J 108.6 . . ?
C00I C00H H00I 110.3 . . ?
C00I C00H H00J 110.3 . . ?
C00H C00I H00K 110.5 . . ?
C00H C00I H00L 110.5 . . ?
H00K C00I H00L 108.7 . . ?
C00J C00I C00H 106.0(2) . . ?
C00J C00I H00K 110.5 . . ?
C00J C00I H00L 110.5 . . ?
C00E C00J H00M 110.2 . . ?
C00E C00J H00N 110.2 . . ?
C00I C00J C00E 107.4(3) . . ?
C00I C00J H00M 110.2 . . ?
C00I C00J H00N 110.2 . . ?
H00M C00J H00N 108.5 . . ?

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
N002 C00E C00J C00I 5.5(4) . . . . ?
N002 C00H C00I C00J -23.5(4) . . . . ?
N003 C006 C009 C007 179.2(2) . . . . ?
N003 C006 C009 N008 -0.1(3) . . . . ?
N003 C006 C00B O001 79.0(3) . . . . ?
N003 C00C C00E N002 70.6(3) . . . . ?
N003 C00C C00E C00J -172.1(2) . . . . ?
C006 N003 N00A N008 -0.1(3) . . . . ?
C006 N003 C00C C00E -96.7(3) . . . . ?
C009 C006 C00B O001 -99.9(3) . . . . ?
C009 C007 C00D N004 179.2(2) . . . . ?
C009 C007 C00G N005 -178.9(2) . . . . ?
C009 N008 N00A N003 0.1(3) . . . . ?
N00A N003 C006 C009 0.1(3) . . . . ?
N00A N003 C006 C00B -179.1(2) . . . . ?
N00A N003 C00C C00E 81.4(3) . . . . ?
N00A N008 C009 C006 0.0(3) . . . . ?
N00A N008 C009 C007 -179.4(2) . . . . ?
C00B C006 C009 C007 -1.8(5) . . . . ?
C00B C006 C009 N008 179.0(2) . . . . ?
C00C N003 C006 C009 178.3(2) . . . . ?
C00C N003 C006 C00B -0.8(4) . . . . ?
C00C N003 N00A N008 -178.6(2) . . . . ?
C00C C00E C00J C00I -114.8(3) . . . . ?
C00D N004 C00F N005 0.6(5) . . . . ?
C00D C007 C009 C006 10.5(4) . . . . ?
C00D C007 C009 N008 -170.3(3) . . . . ?
C00D C007 C00G N005 -0.5(4) . . . . ?
C00E N002 C00H C00I 27.2(3) . . . . ?
C00F N004 C00D C007 -1.0(4) . . . . ?
C00F N005 C00G C007 0.1(4) . . . . ?
C00G N005 C00F N004 -0.2(5) . . . . ?
C00G C007 C009 C006 -171.3(2) . . . . ?
C00G C007 C009 N008 7.9(3) . . . . ?
C00G C007 C00D N004 0.9(4) . . . . ?
C00H N002 C00E C00C 99.7(2) . . . . ?
C00H N002 C00E C00J -20.1(3) . . . . ?
C00H C00I C00J C00E 10.8(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 2.106
_oxdiff_exptl_absorpt_empirical_full_min 0.568
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -0.1(4)
2 1.1(4)

####################################################################### 
# 
# 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_flavia2_auto
_database_code_depnum_ccdc_archive 'CCDC 2423532'
loop_
_audit_author_name
_audit_author_address
'Maureen Gumbo'
;Chalmers University of Technology
Sweden
;
_audit_update_record             
;
2025-02-13 deposited with the CCDC.	2025-08-19 downloaded from the CCDC.
;
_audit_creation_date             2025-02-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 N4 O'
_chemical_formula_sum            'C20 H22 N4 O'
_chemical_formula_weight         334.41
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.4836(2)
_cell_length_b                   6.00559(14)
_cell_length_c                   12.6737(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.456(2)
_cell_angle_gamma                90
_cell_volume                     859.54(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5375
_cell_measurement_temperature    107.02(10)
_cell_measurement_theta_max      75.1450
_cell_measurement_theta_min      3.5300
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic whiteish white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             356
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -1 2 0.0146
7 0 -2 0.0269
2 -4 -2 0.0610
0 4 1 0.0707
-7 0 3 0.0098
7 0 -3 0.0245
2 0 7 0.0209
-2 0 -7 0.0169

_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.3387 -0.6570 1.8552 -0.4265 0.1043 0.8984
7.4248 0.2421 -2.0367 0.3290 -0.0811 -0.9409
1.9406 -3.6923 -1.9513 -0.8256 0.1959 -0.5292
-0.0486 3.8360 1.4633 0.9293 -0.2213 0.2957
-7.2544 -0.0253 3.3281 -0.2831 -0.0868 0.9552
7.2420 0.0927 -3.3704 0.2998 0.0917 -0.9496
2.3556 -0.1209 7.1943 -0.0252 -0.9819 -0.1878
-1.8806 0.0463 -7.4456 0.0253 0.9925 0.1195

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8807
_diffrn_reflns_point_group_measured_fraction_full 0.891
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.263
_diffrn_reflns_theta_min         3.546
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      107.02(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  92.00   0.50    1.02    --  109.13 -95.00-180.00  114
  2  ω    109.00 178.00   0.50    1.02    --  109.13 104.00-132.00  138
  3  ω     35.00  79.00   0.50    1.02    --  109.13 -77.00 120.00   88
  4  ω     35.00  92.00   0.50    1.02    --  109.13-104.00 126.00  114
  5  ω      6.00  79.00   0.50    0.26    --   43.31-104.00 126.00  146
  6  ω     35.00  79.00   0.50    1.02    --  109.13 -77.00-180.00   88
  7  ω    -42.00  31.00   0.50    0.26    --  -43.31  57.00 -30.00  146
  8  ω    -15.00  34.00   0.50    0.26    --  -43.31  38.00  30.00   98
  9  ω    -15.00  34.00   0.50    0.26    --  -43.31  38.00 -60.00   98
 10  ω    -15.00  34.00   0.50    0.26    --  -43.31  38.00 -90.00   98
 11  ω    -15.00  34.00   0.50    0.26    --  -43.31  38.00-180.00   98
 12  ω   -120.00 -29.00   0.50    0.26    --  -43.31 -38.00-120.00  182
 13  ω   -120.00 -58.00   0.50    0.26    --  -43.31 -38.00 -60.00  124
 14  ω   -120.00 -29.00   0.50    0.26    --  -43.31 -38.00   0.00  182
 15  ω   -120.00 -29.00   0.50    0.26    --  -43.31 -38.00 150.00  182
 16  ω   -174.00-103.00   0.50    1.02    -- -104.50-104.00 126.00  142
 17  ω   -163.00 -90.00   0.50    1.02    -- -104.50 -30.00 150.00  146
 18  ω   -132.00 -89.00   0.50    1.02    -- -104.50 -15.00 -30.00   86
 19  ω   -132.00 -89.00   0.50    1.02    -- -104.50 -15.00  60.00   86
 20  ω   -132.00 -89.00   0.50    1.02    -- -104.50 -15.00  90.00   86
 21  ω   -174.00-103.00   0.50    1.02    -- -104.50 -77.00 -90.00  142
 22  ω   -174.00-103.00   0.50    1.02    -- -104.50 -77.00 -90.00  142
 23  ω   -132.00 -89.00   0.50    1.02    -- -104.50 -15.00-180.00   86
 24  ω    -72.00 -30.00   0.50    1.02    -- -104.50  77.00-150.00   84
 25  ω    -92.00 -30.00   0.50    1.02    -- -104.50 104.00-132.00  124
 26  ω    -79.00   0.00   0.50    0.26    --  -43.31 104.00-132.00  158
 27  ω    -72.00 -30.00   0.50    1.02    -- -104.50  77.00 -30.00   84
 28  ω    -72.00 -30.00   0.50    1.02    -- -104.50  77.00   0.00   84
 29  ω   -101.00 -33.00   0.50    1.02    -- -104.50 125.00 150.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0334379000
_diffrn_orient_matrix_UB_12      0.2466131000
_diffrn_orient_matrix_UB_13      -0.0103035000
_diffrn_orient_matrix_UB_21      -0.0440799000
_diffrn_orient_matrix_UB_22      -0.0116148000
_diffrn_orient_matrix_UB_23      -0.1222418000
_diffrn_orient_matrix_UB_31      -0.1246296000
_diffrn_orient_matrix_UB_32      0.0694426000
_diffrn_orient_matrix_UB_33      0.0158665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.585
_reflns_Friedel_fraction_full    0.758
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                2763
_reflns_number_total             2986
_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 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.144a 64-bit (release 23-01-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_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         0.216
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 975 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(2)
_refine_ls_extinction_coef       0.0029(8)
_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   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.109
_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)+(0.0421P)²+0.3402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.1009
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B), C17(H17A,H17B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C21(H21), C5(H5), C25(H25), C3(H3), C24(H24), C23(H23),
 C22(H22), C4(H4)
2.d Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
O19 O 0.22210(18) 0.2952(3) 0.30711(16) 0.0315(5) Uani 1 1 d . . . . .
H19 H 0.220790 0.349479 0.367975 0.047 Uiso 1 1 calc R U . . .
N10 N 0.38246(18) 0.7268(4) 0.37142(19) 0.0238(5) Uani 1 1 d . . . . .
N9 N 0.49626(19) 0.7904(4) 0.40375(19) 0.0270(5) Uani 1 1 d . . . . .
N8 N 0.56078(19) 0.6754(4) 0.34719(19) 0.0264(5) Uani 1 1 d . . . . .
N13 N 0.24221(19) 0.4657(4) 0.51042(19) 0.0254(5) Uani 1 1 d . . . . .
H13 H 0.293(3) 0.368(6) 0.550(3) 0.030 Uiso 1 1 d . U . . .
C11 C 0.3738(2) 0.5685(5) 0.2942(2) 0.0234(6) Uani 1 1 d . . . . .
C2 C 0.4919(2) 0.1725(5) 0.1823(2) 0.0291(6) Uani 1 1 d . . . . .
H2 H 0.426174 0.122731 0.211987 0.035 Uiso 1 1 calc R U . . .
C20 C 0.1620(2) 0.6275(5) 0.1971(2) 0.0231(6) Uani 1 1 d . . . . .
C7 C 0.4889(2) 0.5361(5) 0.2797(2) 0.0244(6) Uani 1 1 d . . . . .
C18 C 0.2592(2) 0.4593(5) 0.2409(2) 0.0250(6) Uani 1 1 d . . . . .
H18 H 0.277844 0.378467 0.176973 0.030 Uiso 1 1 calc R U . . .
C14 C 0.2831(2) 0.7003(5) 0.5299(2) 0.0245(6) Uani 1 1 d . . . . .
H14 H 0.361575 0.701506 0.579347 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2934(2) 0.8225(5) 0.4273(2) 0.0247(6) Uani 1 1 d . . . . .
H12A H 0.215554 0.819944 0.378591 0.030 Uiso 1 1 calc R U . . .
H12B H 0.313911 0.980067 0.444604 0.030 Uiso 1 1 calc R U . . .
C15 C 0.1907(2) 0.8167(5) 0.5848(2) 0.0263(6) Uani 1 1 d . . . . .
H15A H 0.229422 0.917202 0.642569 0.032 Uiso 1 1 calc R U . . .
H15B H 0.134402 0.904162 0.532289 0.032 Uiso 1 1 calc R U . . .
C1 C 0.5381(2) 0.3851(5) 0.2072(2) 0.0263(6) Uani 1 1 d . . . . .
C17 C 0.1258(2) 0.4506(5) 0.5441(3) 0.0314(7) Uani 1 1 d . . . . .
H17A H 0.114234 0.300646 0.572955 0.038 Uiso 1 1 calc R U . . .
H17B H 0.061060 0.480303 0.482775 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6366(2) 0.4538(6) 0.1645(2) 0.0288(6) Uani 1 1 d . . . . .
H6 H 0.668925 0.598202 0.180206 0.035 Uiso 1 1 calc R U . . .
C21 C 0.0461(2) 0.5911(5) 0.2094(2) 0.0293(6) Uani 1 1 d . . . . .
H21 H 0.026484 0.461712 0.245598 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6868(3) 0.3107(6) 0.0993(2) 0.0332(7) Uani 1 1 d . . . . .
H5 H 0.754931 0.356538 0.072233 0.040 Uiso 1 1 calc R U . . .
C25 C 0.1882(2) 0.8138(5) 0.1417(2) 0.0263(6) Uani 1 1 d . . . . .
H25 H 0.267228 0.837996 0.131746 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5409(3) 0.0336(6) 0.1148(2) 0.0339(7) Uani 1 1 d . . . . .
H3 H 0.507412 -0.109182 0.096892 0.041 Uiso 1 1 calc R U . . .
C16 C 0.1278(3) 0.6263(5) 0.6305(3) 0.0332(7) Uani 1 1 d . . . . .
H16A H 0.172735 0.575180 0.700401 0.040 Uiso 1 1 calc R U . . .
H16B H 0.046707 0.668970 0.638916 0.040 Uiso 1 1 calc R U . . .
C24 C 0.1005(3) 0.9665(6) 0.1004(2) 0.0346(7) Uani 1 1 d . . . . .
H24 H 0.119859 1.094334 0.062936 0.042 Uiso 1 1 calc R U . . .
C23 C -0.0150(3) 0.9313(6) 0.1141(3) 0.0389(8) Uani 1 1 d . . . . .
H23 H -0.075401 1.034642 0.086213 0.047 Uiso 1 1 calc R U . . .
C22 C -0.0415(3) 0.7444(6) 0.1689(3) 0.0392(8) Uani 1 1 d . . . . .
H22 H -0.120476 0.720207 0.178908 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6390(3) 0.1026(6) 0.0733(2) 0.0352(7) Uani 1 1 d . . . . .
H4 H 0.672877 0.007148 0.027307 0.042 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
O19 H19 0.8400 . ?
O19 C18 1.410(3) . ?
N10 N9 1.352(3) . ?
N10 C11 1.355(4) . ?
N10 C12 1.463(3) . ?
N9 N8 1.316(3) . ?
N8 C7 1.363(4) . ?
N13 H13 0.91(4) . ?
N13 C14 1.491(4) . ?
N13 C17 1.478(3) . ?
C11 C7 1.381(4) . ?
C11 C18 1.515(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.397(4) . ?
C2 C3 1.386(4) . ?
C20 C18 1.533(4) . ?
C20 C21 1.385(4) . ?
C20 C25 1.383(4) . ?
C7 C1 1.475(4) . ?
C18 H18 1.0000 . ?
C14 H14 1.0000 . ?
C14 C12 1.518(4) . ?
C14 C15 1.538(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.522(4) . ?
C1 C6 1.401(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.517(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.389(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(5) . ?
C25 H25 0.9500 . ?
C25 C24 1.392(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C24 H24 0.9500 . ?
C24 C23 1.385(5) . ?
C23 H23 0.9500 . ?
C23 C22 1.382(5) . ?
C22 H22 0.9500 . ?
C4 H4 0.9500 . ?

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
C18 O19 H19 109.5 . . ?
N9 N10 C11 110.9(2) . . ?
N9 N10 C12 117.7(2) . . ?
C11 N10 C12 131.2(2) . . ?
N8 N9 N10 107.2(2) . . ?
N9 N8 C7 109.1(2) . . ?
C14 N13 H13 111(2) . . ?
C17 N13 H13 109(2) . . ?
C17 N13 C14 106.5(2) . . ?
N10 C11 C7 104.4(2) . . ?
N10 C11 C18 124.7(2) . . ?
C7 C11 C18 130.9(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C21 C20 C18 120.5(3) . . ?
C25 C20 C18 120.4(2) . . ?
C25 C20 C21 119.1(3) . . ?
N8 C7 C11 108.4(2) . . ?
N8 C7 C1 120.8(2) . . ?
C11 C7 C1 130.8(3) . . ?
O19 C18 C11 111.7(2) . . ?
O19 C18 C20 113.4(2) . . ?
O19 C18 H18 106.0 . . ?
C11 C18 C20 113.1(2) . . ?
C11 C18 H18 106.0 . . ?
C20 C18 H18 106.0 . . ?
N13 C14 H14 109.4 . . ?
N13 C14 C12 112.7(2) . . ?
N13 C14 C15 106.4(2) . . ?
C12 C14 H14 109.4 . . ?
C12 C14 C15 109.6(2) . . ?
C15 C14 H14 109.4 . . ?
N10 C12 C14 113.3(2) . . ?
N10 C12 H12A 108.9 . . ?
N10 C12 H12B 108.9 . . ?
C14 C12 H12A 108.9 . . ?
C14 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C16 C15 C14 104.1(2) . . ?
C16 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
C2 C1 C7 122.0(3) . . ?
C2 C1 C6 118.9(3) . . ?
C6 C1 C7 119.1(3) . . ?
N13 C17 H17A 110.6 . . ?
N13 C17 H17B 110.6 . . ?
N13 C17 C16 105.7(2) . . ?
H17A C17 H17B 108.7 . . ?
C16 C17 H17A 110.6 . . ?
C16 C17 H17B 110.6 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.9(3) . . ?
C22 C21 H21 120.0 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C20 C25 H25 119.5 . . ?
C20 C25 C24 121.0(3) . . ?
C24 C25 H25 119.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C15 C16 H16A 111.5 . . ?
C15 C16 H16B 111.5 . . ?
C17 C16 C15 101.2(2) . . ?
C17 C16 H16A 111.5 . . ?
C17 C16 H16B 111.5 . . ?
H16A C16 H16B 109.4 . . ?
C25 C24 H24 120.1 . . ?
C23 C24 C25 119.7(3) . . ?
C23 C24 H24 120.1 . . ?
C24 C23 H23 120.3 . . ?
C22 C23 C24 119.3(3) . . ?
C22 C23 H23 120.3 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?

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
N10 N9 N8 C7 -0.8(3) . . . . ?
N10 C11 C7 N8 -0.5(3) . . . . ?
N10 C11 C7 C1 179.8(3) . . . . ?
N10 C11 C18 O19 -77.9(3) . . . . ?
N10 C11 C18 C20 51.4(4) . . . . ?
N9 N10 C11 C7 0.0(3) . . . . ?
N9 N10 C11 C18 179.5(3) . . . . ?
N9 N10 C12 C14 -84.0(3) . . . . ?
N9 N8 C7 C11 0.8(3) . . . . ?
N9 N8 C7 C1 -179.4(2) . . . . ?
N8 C7 C1 C2 144.6(3) . . . . ?
N8 C7 C1 C6 -33.3(4) . . . . ?
N13 C14 C12 N10 -63.5(3) . . . . ?
N13 C14 C15 C16 20.3(3) . . . . ?
N13 C17 C16 C15 39.9(3) . . . . ?
C11 N10 N9 N8 0.5(3) . . . . ?
C11 N10 C12 C14 91.1(3) . . . . ?
C11 C7 C1 C2 -35.7(5) . . . . ?
C11 C7 C1 C6 146.4(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C20 C21 C22 C23 1.3(5) . . . . ?
C20 C25 C24 C23 -0.4(4) . . . . ?
C7 C11 C18 O19 101.4(3) . . . . ?
C7 C11 C18 C20 -129.2(3) . . . . ?
C7 C1 C6 C5 177.6(3) . . . . ?
C18 C11 C7 N8 -179.9(3) . . . . ?
C18 C11 C7 C1 0.4(5) . . . . ?
C18 C20 C21 C22 -179.7(3) . . . . ?
C18 C20 C25 C24 179.2(3) . . . . ?
C14 N13 C17 C16 -27.9(3) . . . . ?
C14 C15 C16 C17 -36.1(3) . . . . ?
C12 N10 N9 N8 176.5(2) . . . . ?
C12 N10 C11 C7 -175.3(3) . . . . ?
C12 N10 C11 C18 4.2(5) . . . . ?
C12 C14 C15 C16 142.4(2) . . . . ?
C15 C14 C12 N10 178.2(2) . . . . ?
C1 C2 C3 C4 1.7(4) . . . . ?
C1 C6 C5 C4 1.8(4) . . . . ?
C17 N13 C14 C12 -115.7(2) . . . . ?
C17 N13 C14 C15 4.4(3) . . . . ?
C6 C5 C4 C3 -1.4(4) . . . . ?
C21 C20 C18 O19 -10.0(4) . . . . ?
C21 C20 C18 C11 -138.4(3) . . . . ?
C21 C20 C25 C24 1.3(4) . . . . ?
C25 C20 C18 O19 172.1(2) . . . . ?
C25 C20 C18 C11 43.6(3) . . . . ?
C25 C20 C21 C22 -1.7(4) . . . . ?
C25 C24 C23 C22 0.0(5) . . . . ?
C3 C2 C1 C7 -179.3(3) . . . . ?
C3 C2 C1 C6 -1.4(4) . . . . ?
C24 C23 C22 C21 -0.5(5) . . . . ?

_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 1.388
_oxdiff_exptl_absorpt_empirical_full_min 0.790
