# 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_exp_13843_auto
_database_code_depnum_ccdc_archive 'CCDC 2413982'
loop_
_audit_author_name
_audit_author_address
'Han Zhang'
;Huaqiao University
China
;
_audit_update_record             
;
2025-01-01 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;
_audit_creation_date             2024-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
3-(1-imino-2-methyl-3-oxo-9-phenyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-yl)-2,2-dimethylpropanenitrile
_chemical_formula_moiety         'C23 H21 N3 O'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.43
_chemical_melting_point          401.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   22.050(2)
_cell_length_b                   8.2245(13)
_cell_length_c                   21.735(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.182(11)
_cell_angle_gamma                90
_cell_volume                     3879.4(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2395
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2280
_cell_measurement_theta_min      3.1630
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9870
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.758
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  42.80   0.90    1.50    --   17.12 -30.00-165.00   92
  2  ω    -40.00   8.60   0.90    1.50    --  -17.59  30.00  -4.00   54
  3  ω     38.00  75.80   0.90    1.50    --   17.12-178.00-150.00   42
  4  ω    -38.00  -2.00   0.90    1.50    --  -17.59 -77.00  90.00   40
  5  ω    -32.00   6.70   0.90    1.50    --  -17.59 -77.00-180.00   43
  6  ω    -22.00  10.40   0.90    1.50    --  -17.59 -77.00   0.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0005486000
_diffrn_orient_matrix_UB_12      -0.0484856000
_diffrn_orient_matrix_UB_13      0.0270757000
_diffrn_orient_matrix_UB_21      -0.0126232000
_diffrn_orient_matrix_UB_22      0.0653077000
_diffrn_orient_matrix_UB_23      0.0149365000
_diffrn_orient_matrix_UB_31      -0.0301381000
_diffrn_orient_matrix_UB_32      -0.0282493000
_diffrn_orient_matrix_UB_33      -0.0121304000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2636
_reflns_number_total             3961
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1348
_refine_ls_R_factor_gt           0.0955
_refine_ls_restrained_S_all      1.092
_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)+(0.0715P)²+10.2807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2265
_refine_ls_wR_factor_ref         0.2472
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N3) = Uanis(N3A)
Uanis(C23) = Uanis(C23A)
Uanis(C22) = Uanis(C22A)
4. Others
 Sof(N3A)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C23A)=1-FVAR(1)
 Sof(N3)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C23)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C22A(H22D,H22E,
 H22F)
;
_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 0.40212(14) 0.4448(5) 0.46554(14) 0.0885(11) Uani 1 1 d . . . . .
N1 N 0.34078(13) 0.5249(4) 0.37330(14) 0.0552(9) Uani 1 1 d . . . . .
N2 N 0.42459(15) 0.4615(5) 0.24994(18) 0.0646(10) Uani 1 1 d D . . . .
N3 N 0.4324(4) 0.8643(12) 0.2864(4) 0.0873(18) Uani 0.511(6) 1 d . . P A 1
N3A N 0.4335(4) 0.8398(12) 0.4785(4) 0.0873(18) Uani 0.489(6) 1 d . . P A 2
C1 C 0.39492(18) 0.4711(6) 0.41001(19) 0.0611(11) Uani 1 1 d . . . . .
C2 C 0.44135(17) 0.4471(5) 0.36600(19) 0.0565(10) Uani 1 1 d . . . . .
C3 C 0.40369(15) 0.4805(5) 0.30062(18) 0.0493(9) Uani 1 1 d . . . . .
C4 C 0.34216(15) 0.5292(5) 0.30920(17) 0.0479(9) Uani 1 1 d . . . . .
C5 C 0.28568(15) 0.5731(4) 0.27666(17) 0.0469(9) Uani 1 1 d . . . . .
C6 C 0.24711(16) 0.6002(5) 0.32408(19) 0.0528(10) Uani 1 1 d . . . . .
C7 C 0.28224(17) 0.5684(5) 0.38331(19) 0.0576(10) Uani 1 1 d . . . . .
C8 C 0.2596(2) 0.5860(7) 0.4387(2) 0.0774(14) Uani 1 1 d . . . . .
H8 H 0.2839 0.5655 0.4774 0.093 Uiso 1 1 calc R . . . .
C9 C 0.1994(2) 0.6355(7) 0.4329(3) 0.0842(15) Uani 1 1 d . . . . .
H9 H 0.1821 0.6462 0.4687 0.101 Uiso 1 1 calc R . . . .
C10 C 0.1635(2) 0.6701(7) 0.3750(3) 0.0829(15) Uani 1 1 d . . . . .
H10 H 0.1233 0.7060 0.3732 0.099 Uiso 1 1 calc R . . . .
C11 C 0.18648(18) 0.6523(6) 0.3205(2) 0.0667(12) Uani 1 1 d . . . . .
H11 H 0.1620 0.6746 0.2820 0.080 Uiso 1 1 calc R . . . .
C12 C 0.26594(15) 0.5917(5) 0.20868(17) 0.0465(9) Uani 1 1 d . . . . .
C13 C 0.21055(18) 0.5282(6) 0.1787(2) 0.0665(12) Uani 1 1 d . . . . .
H13 H 0.1856 0.4707 0.2014 0.080 Uiso 1 1 calc R . . . .
C14 C 0.1922(2) 0.5498(7) 0.1151(2) 0.0761(14) Uani 1 1 d . . . . .
H14 H 0.1543 0.5087 0.0957 0.091 Uiso 1 1 calc R . . . .
C15 C 0.2281(2) 0.6298(7) 0.0803(2) 0.0792(15) Uani 1 1 d . . . . .
H15 H 0.2153 0.6419 0.0374 0.095 Uiso 1 1 calc R . . . .
C16 C 0.2833(2) 0.6924(8) 0.1090(2) 0.0874(17) Uani 1 1 d . . . . .
H16 H 0.3084 0.7468 0.0857 0.105 Uiso 1 1 calc R . . . .
C17 C 0.30175(18) 0.6747(6) 0.1730(2) 0.0707(13) Uani 1 1 d . . . . .
H17 H 0.3390 0.7196 0.1923 0.085 Uiso 1 1 calc R . . . .
C18 C 0.4633(2) 0.2691(6) 0.3693(2) 0.0861(15) Uani 1 1 d . . . . .
H18A H 0.4286 0.1984 0.3576 0.129 Uiso 1 1 calc GR . . . .
H18B H 0.4833 0.2444 0.4111 0.129 Uiso 1 1 calc GR . . . .
H18C H 0.4918 0.2536 0.3411 0.129 Uiso 1 1 calc GR . . . .
C19 C 0.49841(16) 0.5585(5) 0.38450(19) 0.0565(10) Uani 1 1 d . . . . .
H19A H 0.5198 0.5220 0.4250 0.068 Uiso 1 1 calc R . . . .
H19B H 0.5257 0.5379 0.3549 0.068 Uiso 1 1 calc R . . . .
C20 C 0.49112(16) 0.7432(5) 0.38852(19) 0.0572(10) Uani 1 1 d . . . . .
C21 C 0.5569(2) 0.8161(7) 0.4029(3) 0.0895(16) Uani 1 1 d . . . . .
H21A H 0.5794 0.7671 0.4401 0.134 Uiso 1 1 calc GR . . . .
H21B H 0.5543 0.9313 0.4089 0.134 Uiso 1 1 calc GR . . . .
H21C H 0.5777 0.7950 0.3685 0.134 Uiso 1 1 calc GR . . . .
C22 C 0.4554(9) 0.779(2) 0.4432(9) 0.090(6) Uani 0.511(6) 1 d . . P A 1
H22A H 0.4120 0.7635 0.4287 0.134 Uiso 0.511(6) 1 calc GR . P A 1
H22B H 0.4629 0.8888 0.4572 0.134 Uiso 0.511(6) 1 calc GR . P A 1
H22C H 0.4692 0.7056 0.4772 0.134 Uiso 0.511(6) 1 calc GR . P A 1
C22A C 0.4560(11) 0.828(3) 0.3307(11) 0.090(6) Uani 0.489(6) 1 d . . P A 2
H22D H 0.4722 0.7938 0.2946 0.134 Uiso 0.489(6) 1 calc GR . P A 2
H22E H 0.4605 0.9435 0.3356 0.134 Uiso 0.489(6) 1 calc GR . P A 2
H22F H 0.4131 0.7997 0.3255 0.134 Uiso 0.489(6) 1 calc GR . P A 2
C23 C 0.4586(6) 0.809(2) 0.3275(8) 0.050(3) Uani 0.511(6) 1 d . . P A 1
C23A C 0.4607(6) 0.802(2) 0.4393(8) 0.050(3) Uani 0.489(6) 1 d . . P A 2
H2 H 0.397(2) 0.499(7) 0.220(2) 0.12(2) Uiso 1 1 d 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 C1 1.209(5) . ?
N1 C1 1.386(5) . ?
N1 C4 1.399(5) . ?
N1 C7 1.393(5) . ?
N2 C3 1.277(5) . ?
N2 H2 0.86(2) . ?
N3 C23 1.075(19) . ?
N3A C23A 1.168(19) . ?
C1 C2 1.532(6) . ?
C2 C3 1.538(5) . ?
C2 C18 1.540(6) . ?
C2 C19 1.551(5) . ?
C3 C4 1.458(5) . ?
C4 C5 1.367(5) . ?
C5 C6 1.465(5) . ?
C5 C12 1.473(5) . ?
C6 C7 1.405(5) . ?
C6 C11 1.393(5) . ?
C7 C8 1.389(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(5) . ?
C12 C17 1.382(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.358(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(6) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.532(6) . ?
C20 C21 1.548(5) . ?
C20 C22 1.565(19) . ?
C20 C22A 1.52(2) . ?
C20 C23 1.495(18) . ?
C20 C23A 1.471(18) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 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
C1 N1 C4 114.4(3) . . ?
C1 N1 C7 136.0(3) . . ?
C7 N1 C4 109.4(3) . . ?
C3 N2 H2 107(4) . . ?
O1 C1 N1 125.4(4) . . ?
O1 C1 C2 128.0(4) . . ?
N1 C1 C2 106.5(3) . . ?
C1 C2 C3 104.0(3) . . ?
C1 C2 C18 109.5(4) . . ?
C1 C2 C19 111.3(3) . . ?
C3 C2 C18 109.1(4) . . ?
C3 C2 C19 114.5(3) . . ?
C18 C2 C19 108.4(3) . . ?
N2 C3 C2 123.8(3) . . ?
N2 C3 C4 129.1(3) . . ?
C4 C3 C2 107.1(3) . . ?
N1 C4 C3 107.7(3) . . ?
C5 C4 N1 110.1(3) . . ?
C5 C4 C3 142.1(4) . . ?
C4 C5 C6 105.4(3) . . ?
C4 C5 C12 128.8(3) . . ?
C6 C5 C12 125.8(3) . . ?
C7 C6 C5 108.8(3) . . ?
C11 C6 C5 132.7(4) . . ?
C11 C6 C7 118.5(4) . . ?
N1 C7 C6 106.3(3) . . ?
C8 C7 N1 130.3(4) . . ?
C8 C7 C6 123.4(4) . . ?
C7 C8 H8 121.9 . . ?
C9 C8 C7 116.2(5) . . ?
C9 C8 H8 121.9 . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 121.9(5) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.4(4) . . ?
C11 C10 H10 119.3 . . ?
C6 C11 H11 120.7 . . ?
C10 C11 C6 118.6(4) . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C5 120.9(3) . . ?
C13 C12 C17 117.9(4) . . ?
C17 C12 C5 121.2(3) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(4) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.5(4) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.2(4) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(5) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 121.3(4) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C19 H19A 107.1 . . ?
C2 C19 H19B 107.1 . . ?
H19A C19 H19B 106.8 . . ?
C20 C19 C2 120.8(3) . . ?
C20 C19 H19A 107.1 . . ?
C20 C19 H19B 107.1 . . ?
C19 C20 C21 106.9(3) . . ?
C19 C20 C22 107.5(8) . . ?
C21 C20 C22 110.7(8) . . ?
C22A C20 C19 116.7(9) . . ?
C22A C20 C21 108.1(10) . . ?
C23 C20 C19 110.4(7) . . ?
C23 C20 C21 108.9(7) . . ?
C23 C20 C22 112.3(10) . . ?
C23A C20 C19 115.8(7) . . ?
C23A C20 C21 104.8(7) . . ?
C23A C20 C22A 103.6(10) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C22A H22D 109.5 . . ?
C20 C22A H22E 109.5 . . ?
C20 C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
N3 C23 C20 173.9(15) . . ?
N3A C23A C20 175.0(15) . . ?

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
C14 H14 N3A 0.93 2.68 3.579(10) 163.2 4_545
C19 H19A O1 0.97 2.69 3.593(5) 154.5 5_666
C21 H21A O1 0.96 2.67 3.562(7) 155.3 5_666
C22 H22A N1 0.96 2.67 3.419(19) 135.8 .

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
O1 C1 C2 C3 173.3(5) . . . . ?
O1 C1 C2 C18 56.8(6) . . . . ?
O1 C1 C2 C19 -62.9(6) . . . . ?
N1 C1 C2 C3 -4.7(4) . . . . ?
N1 C1 C2 C18 -121.1(4) . . . . ?
N1 C1 C2 C19 119.1(4) . . . . ?
N1 C4 C5 C6 1.0(4) . . . . ?
N1 C4 C5 C12 -179.4(3) . . . . ?
N1 C7 C8 C9 178.2(5) . . . . ?
N2 C3 C4 N1 177.0(4) . . . . ?
N2 C3 C4 C5 -0.7(9) . . . . ?
C1 N1 C4 C3 -2.5(5) . . . . ?
C1 N1 C4 C5 175.9(3) . . . . ?
C1 N1 C7 C6 -175.5(4) . . . . ?
C1 N1 C7 C8 6.7(8) . . . . ?
C1 C2 C3 N2 -174.6(4) . . . . ?
C1 C2 C3 C4 3.3(4) . . . . ?
C1 C2 C19 C20 -56.9(5) . . . . ?
C2 C3 C4 N1 -0.7(4) . . . . ?
C2 C3 C4 C5 -178.4(5) . . . . ?
C2 C19 C20 C21 -175.7(4) . . . . ?
C2 C19 C20 C22 65.4(9) . . . . ?
C2 C19 C20 C22A -54.5(11) . . . . ?
C2 C19 C20 C23 -57.3(7) . . . . ?
C2 C19 C20 C23A 68.0(8) . . . . ?
C3 C2 C19 C20 60.7(5) . . . . ?
C3 C4 C5 C6 178.6(5) . . . . ?
C3 C4 C5 C12 -1.8(8) . . . . ?
C4 N1 C1 O1 -173.4(4) . . . . ?
C4 N1 C1 C2 4.7(5) . . . . ?
C4 N1 C7 C6 0.0(4) . . . . ?
C4 N1 C7 C8 -177.8(5) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C4 C5 C6 C11 177.2(4) . . . . ?
C4 C5 C12 C13 134.8(4) . . . . ?
C4 C5 C12 C17 -46.0(6) . . . . ?
C5 C6 C7 N1 0.6(4) . . . . ?
C5 C6 C7 C8 178.6(4) . . . . ?
C5 C6 C11 C10 -178.2(4) . . . . ?
C5 C12 C13 C14 178.6(4) . . . . ?
C5 C12 C17 C16 -180.0(4) . . . . ?
C6 C5 C12 C13 -45.7(6) . . . . ?
C6 C5 C12 C17 133.5(4) . . . . ?
C6 C7 C8 C9 0.8(7) . . . . ?
C7 N1 C1 O1 2.0(8) . . . . ?
C7 N1 C1 C2 180.0(4) . . . . ?
C7 N1 C4 C3 -179.1(3) . . . . ?
C7 N1 C4 C5 -0.6(4) . . . . ?
C7 C6 C11 C10 -0.1(6) . . . . ?
C7 C8 C9 C10 -1.6(8) . . . . ?
C8 C9 C10 C11 1.7(9) . . . . ?
C9 C10 C11 C6 -0.7(8) . . . . ?
C11 C6 C7 N1 -177.9(4) . . . . ?
C11 C6 C7 C8 0.1(6) . . . . ?
C12 C5 C6 C7 179.4(4) . . . . ?
C12 C5 C6 C11 -2.4(7) . . . . ?
C12 C13 C14 C15 1.5(8) . . . . ?
C13 C12 C17 C16 -0.8(7) . . . . ?
C13 C14 C15 C16 -1.0(8) . . . . ?
C14 C15 C16 C17 -0.4(9) . . . . ?
C15 C16 C17 C12 1.3(8) . . . . ?
C17 C12 C13 C14 -0.6(7) . . . . ?
C18 C2 C3 N2 -57.9(5) . . . . ?
C18 C2 C3 C4 120.0(4) . . . . ?
C18 C2 C19 C20 -177.3(4) . . . . ?
C19 C2 C3 N2 63.7(5) . . . . ?
C19 C2 C3 C4 -118.4(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 11.920
_oxdiff_exptl_absorpt_empirical_full_min 0.715
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/n-Hexane'
_chemical_properties_physical    Heat-sensitive,Oxygen-sensitive
