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

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

data_scd-gsy2023-0706_auto
_database_code_depnum_ccdc_archive 'CCDC 2335999'
loop_
_audit_author_name
_audit_author_address
'Siyu  Gao'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2024-02-28 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2023-09-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H24 N4 O3'
_chemical_formula_sum            'C23 H24 N4 O3'
_chemical_formula_weight         404.46
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O2
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.99824(7)
_cell_length_b                   13.13119(9)
_cell_length_c                   17.79770(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2102.93(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13066
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9810
_cell_measurement_theta_min      4.1590
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15262
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.906
_diffrn_reflns_theta_min         4.184
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00  -1.00   1.00    2.00    --  -41.76 -19.00  30.00  121
  2  ω    -87.00  -6.00   1.00    2.00    --  -41.76 125.00-180.00   81
  3  ω   -116.00 -17.00   1.00    2.00    --  -41.76 -38.00 -60.00   99
  4  ω     80.00 178.00   1.00    4.00    --  106.05  45.00   0.00   98
  5  ω    103.00 178.00   1.00    4.00    --  106.05  77.00  60.00   75
  6  ω     30.00 139.00   1.00    4.00    --  106.05 -77.00-150.00  109
  7  ω     97.00 178.00   1.00    4.00    --  106.05 125.00 -60.00   81
  8  ω    103.00 178.00   1.00    4.00    --  106.05  77.00-160.00   75
  9  ω    103.00 178.00   1.00    4.00    --  106.05  77.00  30.00   75
 10  ω    103.00 178.00   1.00    4.00    --  106.05  77.00 -90.00   75
 11  ω   -116.00 -17.00   1.00    2.00    --  -41.76 -38.00-180.00   99
 12  ω     14.00 115.00   1.00    2.00    --   41.76  57.00 150.00  101
 13  ω      6.00  83.00   1.00    2.00    --   41.76 -99.00  60.00   77
 14  ω     80.00 178.00   1.00    4.00    --  106.05  45.00 150.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1029699000
_diffrn_orient_matrix_UB_12      0.0714421000
_diffrn_orient_matrix_UB_13      0.0447856000
_diffrn_orient_matrix_UB_21      0.0184975000
_diffrn_orient_matrix_UB_22      -0.0680329000
_diffrn_orient_matrix_UB_23      0.0698888000
_diffrn_orient_matrix_UB_31      0.1354975000
_diffrn_orient_matrix_UB_32      0.0635666000
_diffrn_orient_matrix_UB_33      0.0244816000
_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         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4059
_reflns_number_total             4132
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_coef       0.0338(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.079
_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)+(0.0688P)²+0.3457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C13(H13)
1.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
1.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C23(H23), C19(H19), C12(H12), C20(H20), C10(H10), C11(H11), C22(H22),
 C9(H9), C8(H8), C21(H21)
1.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
1.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5770(3) 0.72902(13) 0.16004(10) 0.0561(5) Uani 1 1 d . . . . .
O1 O 0.4129(2) 0.45121(13) 0.22656(11) 0.0577(5) Uani 1 1 d . . . . .
H1 H 0.3835 0.3981 0.2457 0.087 Uiso 1 1 calc R U . . .
O2 O 0.3099(2) 0.57105(19) 0.35869(13) 0.0707(6) Uani 1 1 d . . . . .
N2 N 0.6339(2) 0.42872(13) 0.37836(10) 0.0389(4) Uani 1 1 d . . . . .
N1 N 0.5069(2) 0.47912(14) 0.40708(11) 0.0404(4) Uani 1 1 d . . . . .
N3 N 0.6718(3) 0.75203(15) 0.22228(12) 0.0497(5) Uani 1 1 d . . . . .
C4 C 0.5569(3) 0.60048(16) 0.24110(12) 0.0402(5) Uani 1 1 d . . . . .
C18 C 0.7403(2) 0.67288(15) 0.33999(13) 0.0384(5) Uani 1 1 d . . . . .
N4 N 0.4129(4) 0.6063(2) 0.12169(15) 0.0778(9) Uani 1 1 d . . . . .
H4 H 0.3788 0.5456 0.1272 0.093 Uiso 1 1 calc R U . . .
C13 C 0.7619(3) 0.40015(18) 0.25946(13) 0.0466(5) Uani 1 1 d . . . . .
H13 H 0.8046 0.4595 0.2340 0.056 Uiso 1 1 calc R U . . .
C23 C 0.8910(3) 0.6524(2) 0.34022(15) 0.0499(6) Uani 1 1 d . . . . .
H23 H 0.9414 0.6439 0.2950 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6560(3) 0.67454(16) 0.26803(12) 0.0389(5) Uani 1 1 d . . . . .
C19 C 0.6680(3) 0.68811(19) 0.40778(14) 0.0476(5) Uani 1 1 d . . . . .
H19 H 0.5673 0.7039 0.4081 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5091(3) 0.63948(18) 0.17316(14) 0.0495(6) Uani 1 1 d . . . . .
C3 C 0.5076(3) 0.50270(16) 0.27762(13) 0.0407(5) Uani 1 1 d . . . . .
C7 C 0.4881(3) 0.48392(17) 0.48599(13) 0.0400(5) Uani 1 1 d . . . . .
C12 C 0.5709(3) 0.4203(2) 0.53142(14) 0.0497(6) Uani 1 1 d . . . . .
H12 H 0.6404 0.3762 0.5104 0.060 Uiso 1 1 calc R U . . .
C2 C 0.4245(3) 0.52466(19) 0.35188(14) 0.0449(5) Uani 1 1 d . . . . .
C20 C 0.7441(3) 0.6801(2) 0.47467(15) 0.0572(7) Uani 1 1 d . . . . .
H20 H 0.6946 0.6899 0.5200 0.069 Uiso 1 1 calc R U . . .
C10 C 0.4505(4) 0.4900(3) 0.64077(16) 0.0633(7) Uani 1 1 d . . . . .
H10 H 0.4359 0.4908 0.6925 0.076 Uiso 1 1 calc R U . . .
C11 C 0.5497(4) 0.4228(3) 0.60921(14) 0.0644(8) Uani 1 1 d . . . . .
H11 H 0.6030 0.3786 0.6399 0.077 Uiso 1 1 calc R U . . .
C22 C 0.9670(3) 0.6445(2) 0.40755(19) 0.0635(7) Uani 1 1 d . . . . .
H22 H 1.0683 0.6304 0.4076 0.076 Uiso 1 1 calc R U . . .
C9 C 0.3736(3) 0.5558(2) 0.59546(17) 0.0578(7) Uani 1 1 d . . . . .
H9 H 0.3097 0.6032 0.6169 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3897(3) 0.55269(19) 0.51793(16) 0.0516(6) Uani 1 1 d . . . . .
H8 H 0.3348 0.5964 0.4876 0.062 Uiso 1 1 calc R U . . .
C21 C 0.8931(3) 0.6574(2) 0.47435(18) 0.0625(7) Uani 1 1 d . . . . .
H21 H 0.9441 0.6508 0.5195 0.075 Uiso 1 1 calc R U . . .
C15 C 0.8845(5) 0.3541(4) 0.30440(19) 0.0891(13) Uani 1 1 d . . . . .
H15A H 0.9109 0.3993 0.3447 0.134 Uiso 1 1 calc R U . . .
H15B H 0.9694 0.3433 0.2727 0.134 Uiso 1 1 calc R U . . .
H15C H 0.8522 0.2902 0.3248 0.134 Uiso 1 1 calc R U . . .
C16 C 0.3606(5) 0.6641(2) 0.05691(16) 0.0705(9) Uani 1 1 d . . . . .
H16A H 0.2552 0.6517 0.0501 0.085 Uiso 1 1 calc R U . . .
H16B H 0.3738 0.7362 0.0667 0.085 Uiso 1 1 calc R U . . .
C14 C 0.7096(5) 0.3288(4) 0.1979(2) 0.1029(16) Uani 1 1 d . . . . .
H14A H 0.6739 0.2668 0.2200 0.154 Uiso 1 1 calc R U . . .
H14B H 0.7909 0.3140 0.1648 0.154 Uiso 1 1 calc R U . . .
H14C H 0.6308 0.3606 0.1701 0.154 Uiso 1 1 calc R U . . .
C17 C 0.4371(10) 0.6380(5) -0.0106(3) 0.146(3) Uani 1 1 d . . . . .
H17A H 0.3936 0.6739 -0.0521 0.218 Uiso 1 1 calc R U . . .
H17B H 0.4293 0.5660 -0.0191 0.218 Uiso 1 1 calc R U . . .
H17C H 0.5399 0.6565 -0.0061 0.218 Uiso 1 1 calc R U . . .
C1 C 0.6368(3) 0.43962(15) 0.30691(12) 0.0379(5) Uani 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
O3 N3 1.431(3) . ?
O3 C5 1.345(3) . ?
O1 H1 0.8200 . ?
O1 C3 1.417(3) . ?
O2 C2 1.204(3) . ?
N2 N1 1.416(3) . ?
N2 C1 1.280(3) . ?
N1 C7 1.416(3) . ?
N1 C2 1.369(3) . ?
N3 C6 1.311(3) . ?
C4 C6 1.403(3) . ?
C4 C5 1.382(3) . ?
C4 C3 1.506(3) . ?
C18 C23 1.382(3) . ?
C18 C6 1.489(3) . ?
C18 C19 1.385(3) . ?
N4 H4 0.8600 . ?
N4 C5 1.333(3) . ?
N4 C16 1.458(3) . ?
C13 H13 0.9800 . ?
C13 C15 1.491(4) . ?
C13 C14 1.516(4) . ?
C13 C1 1.500(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.384(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(4) . ?
C3 C2 1.546(3) . ?
C3 C1 1.520(3) . ?
C7 C12 1.381(4) . ?
C7 C8 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.398(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(5) . ?
C10 C9 1.369(5) . ?
C11 H11 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.373(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.388(4) . ?
C8 H8 0.9300 . ?
C21 H21 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.427(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 N3 108.72(17) . . ?
C3 O1 H1 109.5 . . ?
C1 N2 N1 108.83(18) . . ?
N2 N1 C7 118.40(17) . . ?
C2 N1 N2 112.51(18) . . ?
C2 N1 C7 128.8(2) . . ?
C6 N3 O3 104.60(18) . . ?
C6 C4 C3 129.1(2) . . ?
C5 C4 C6 103.9(2) . . ?
C5 C4 C3 127.0(2) . . ?
C23 C18 C6 120.3(2) . . ?
C23 C18 C19 119.1(2) . . ?
C19 C18 C6 120.5(2) . . ?
C5 N4 H4 117.2 . . ?
C5 N4 C16 125.7(3) . . ?
C16 N4 H4 117.2 . . ?
C15 C13 H13 106.2 . . ?
C15 C13 C14 111.5(3) . . ?
C15 C13 C1 113.2(2) . . ?
C14 C13 H13 106.2 . . ?
C1 C13 H13 106.2 . . ?
C1 C13 C14 112.8(3) . . ?
C18 C23 H23 119.9 . . ?
C18 C23 C22 120.1(2) . . ?
C22 C23 H23 119.9 . . ?
N3 C6 C4 113.2(2) . . ?
N3 C6 C18 119.4(2) . . ?
C4 C6 C18 127.39(19) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
O3 C5 C4 109.5(2) . . ?
N4 C5 O3 117.4(2) . . ?
N4 C5 C4 133.0(2) . . ?
O1 C3 C4 107.89(17) . . ?
O1 C3 C2 110.3(2) . . ?
O1 C3 C1 114.82(18) . . ?
C4 C3 C2 110.64(18) . . ?
C4 C3 C1 112.78(19) . . ?
C1 C3 C2 100.29(17) . . ?
C12 C7 N1 119.3(2) . . ?
C12 C7 C8 119.9(2) . . ?
C8 C7 N1 120.8(2) . . ?
C7 C12 H12 120.3 . . ?
C7 C12 C11 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
O2 C2 N1 127.8(2) . . ?
O2 C2 C3 126.5(2) . . ?
N1 C2 C3 105.64(19) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 120.0 . . ?
C10 C9 H9 119.5 . . ?
C10 C9 C8 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.1 . . ?
N4 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 N4 112.7(4) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C1 C13 122.4(2) . . ?
N2 C1 C3 112.7(2) . . ?
C13 C1 C3 124.71(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 0.82 2.06 2.872(3) 169.7 3_645

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
O3 N3 C6 C4 0.0(3) . . . . ?
O3 N3 C6 C18 179.93(19) . . . . ?
O1 C3 C2 O2 -56.6(3) . . . . ?
O1 C3 C2 N1 122.4(2) . . . . ?
O1 C3 C1 N2 -119.3(2) . . . . ?
O1 C3 C1 C13 65.1(3) . . . . ?
N2 N1 C7 C12 -15.4(3) . . . . ?
N2 N1 C7 C8 163.4(2) . . . . ?
N2 N1 C2 O2 178.4(3) . . . . ?
N2 N1 C2 C3 -0.6(2) . . . . ?
N1 N2 C1 C13 176.55(19) . . . . ?
N1 N2 C1 C3 0.8(2) . . . . ?
N1 C7 C12 C11 -178.2(3) . . . . ?
N1 C7 C8 C9 -179.9(2) . . . . ?
N3 O3 C5 C4 -1.2(3) . . . . ?
N3 O3 C5 N4 178.5(3) . . . . ?
C4 C3 C2 O2 62.7(3) . . . . ?
C4 C3 C2 N1 -118.3(2) . . . . ?
C4 C3 C1 N2 116.6(2) . . . . ?
C4 C3 C1 C13 -59.0(3) . . . . ?
C18 C23 C22 C21 -0.3(4) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C23 C18 C6 N3 -74.5(3) . . . . ?
C23 C18 C6 C4 105.4(3) . . . . ?
C23 C18 C19 C20 -1.9(4) . . . . ?
C23 C22 C21 C20 -1.2(5) . . . . ?
C6 C4 C5 O3 1.1(3) . . . . ?
C6 C4 C5 N4 -178.5(3) . . . . ?
C6 C4 C3 O1 -176.9(2) . . . . ?
C6 C4 C3 C2 62.4(3) . . . . ?
C6 C4 C3 C1 -49.0(3) . . . . ?
C6 C18 C23 C22 -175.9(2) . . . . ?
C6 C18 C19 C20 175.8(2) . . . . ?
C19 C18 C23 C22 1.8(4) . . . . ?
C19 C18 C6 N3 107.9(3) . . . . ?
C19 C18 C6 C4 -72.2(3) . . . . ?
C19 C20 C21 C22 1.1(5) . . . . ?
C5 O3 N3 C6 0.7(3) . . . . ?
C5 C4 C6 N3 -0.7(3) . . . . ?
C5 C4 C6 C18 179.4(2) . . . . ?
C5 C4 C3 O1 5.7(3) . . . . ?
C5 C4 C3 C2 -115.0(3) . . . . ?
C5 C4 C3 C1 133.5(3) . . . . ?
C5 N4 C16 C17 99.2(5) . . . . ?
C3 C4 C6 N3 -178.6(2) . . . . ?
C3 C4 C6 C18 1.5(4) . . . . ?
C3 C4 C5 O3 179.1(2) . . . . ?
C3 C4 C5 N4 -0.5(5) . . . . ?
C7 N1 C2 O2 -7.5(4) . . . . ?
C7 N1 C2 C3 173.5(2) . . . . ?
C7 C12 C11 C10 -2.0(5) . . . . ?
C12 C7 C8 C9 -1.1(4) . . . . ?
C2 N1 C7 C12 170.7(2) . . . . ?
C2 N1 C7 C8 -10.4(4) . . . . ?
C2 C3 C1 N2 -1.1(2) . . . . ?
C2 C3 C1 C13 -176.7(2) . . . . ?
C10 C9 C8 C7 -1.8(4) . . . . ?
C11 C10 C9 C8 2.7(5) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C8 C7 C12 C11 2.9(4) . . . . ?
C15 C13 C1 N2 -3.9(4) . . . . ?
C15 C13 C1 C3 171.4(3) . . . . ?
C16 N4 C5 O3 -8.1(5) . . . . ?
C16 N4 C5 C4 171.5(3) . . . . ?
C14 C13 C1 N2 124.0(3) . . . . ?
C14 C13 C1 C3 -60.8(4) . . . . ?
C1 N2 N1 C7 -174.9(2) . . . . ?
C1 N2 N1 C2 -0.1(3) . . . . ?
C1 C3 C2 O2 -178.1(3) . . . . ?
C1 C3 C2 N1 1.0(2) . . . . ?

_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 1.470
_oxdiff_exptl_absorpt_empirical_full_min 0.674
