# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20240387a_auto
_database_code_depnum_ccdc_archive 'CCDC 2341296'
loop_
_audit_author_name
_audit_author_address
yuwang
;Zhengzhou University
China
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-05-17 downloaded from the CCDC.
;
_audit_creation_date             2024-03-18
_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        ?
_chemical_formula_moiety         'C21 H14 N2'
_chemical_formula_sum            'C21 H14 N2'
_chemical_formula_weight         294.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4
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'

_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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   10.0458(2)
_cell_length_b                   10.0442(3)
_cell_length_c                   29.4099(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.558(3)
_cell_angle_gamma                90
_cell_volume                     2934.49(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8482
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9540
_cell_measurement_theta_min      6.0510
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (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    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20404
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.540
_diffrn_reflns_theta_min         6.087
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  37.00   1.00    1.00    --  -33.50  37.00 150.00   93
  2  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  30.00   73
  3  ω    -88.00  -2.00   1.00    1.00    --  -33.50 127.00-147.00   86
  4  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  90.00   73
  5  ω   -106.00  -2.00   1.00    1.00    --  -33.50 -23.00-156.88  104
  6  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 -30.00   93
  7  ω      0.00  29.00   1.00    1.00    --   36.47  91.00  81.13   29
  8  ω     18.00 105.00   1.00    1.00    --   36.47  57.00  30.00   87
  9  ω     -2.00  25.00   1.00    1.00    --   36.47  95.00  -4.12   27
 10  ω     38.00 107.00   1.00    5.00    --  108.00 -94.00  60.00   69
 11  ω    104.00 176.00   1.00    5.00    --  108.00 111.00-120.00   72
 12  ω     38.00 107.00   1.00    5.00    --  108.00 -94.00-150.00   69
 13  ω     64.00 111.00   1.00    5.00    --  108.00 -77.00 120.00   47
 14  ω    118.00 178.00   1.00    5.00    --  108.00  45.00-180.00   60
 15  ω     38.00 122.00   1.00    5.00    --  108.00 -30.00 150.00   84
 16  ω     89.00 116.00   1.00    5.00    --  108.00  45.00-180.00   27
 17  ω     44.00 128.00   1.00    5.00    --  108.00 -45.00  60.00   84
 18  ω    -17.00  22.00   1.00    1.00    --    0.00 -77.00   0.00   39
 19  ω    -56.00  35.00   1.00    1.00    --  -33.50  37.00  30.00   91
 20  ω     62.00 104.00   1.00    1.00    --   36.47 178.00 120.00   42
 21  ω     41.00  81.00   1.00    1.00    --   36.47-127.00 136.00   40
 22  ω      9.00  34.00   1.00    1.00    --   44.00  88.00-107.91   25
 23  ω      9.00  34.00   1.00    1.00    --   44.00  89.00 -13.57   25
 24  ω      8.00  33.00   1.00    1.00    --   44.00  90.00 132.41   25
 25  ω      9.00  34.00   1.00    1.00    --   44.00  88.00-150.34   25
 26  ω     16.00  41.00   1.00    1.00    --   48.00  84.00 100.12   25
 27  ω     17.00  43.00   1.00    1.00    --   48.00  82.00 -63.76   26
 28  ω     16.00  41.00   1.00    1.00    --   48.00  83.00 166.39   25
 29  ω     28.00  54.00   1.00    1.00    --   52.00  73.00  71.20   26
 30  ω     31.00  61.00   1.00    1.00    --   56.00  73.00 159.85   30
 31  ω     30.00  75.00   1.00    1.00    --   56.00  72.00  35.11   45
 32  ω     30.00  64.00   1.00    1.00    --   56.00  72.00-124.02   34
 33  ω     93.00 122.00   1.00    1.00    --   56.00  72.00  35.11   29
 34  ω     40.00  72.00   1.00    1.00    --   60.00  71.00-138.64   32
 35  ω     41.00  67.00   1.00    1.00    --   60.00  61.00  95.25   26
 36  ω     36.00  70.00   1.00    1.00    --   60.00  69.00-169.94   34
 37  ω     36.00  78.00   1.00    1.00    --   60.00  69.00 -19.80   42
 38  ω     91.00 117.00   1.00    1.00    --   60.00  71.00-138.64   26
 39  ω     38.00  77.00   1.00    1.00    --   60.00  65.00 -77.08   39
 40  ω     47.00 127.00   1.00    1.00    --   72.00  71.00  90.81   80
 41  ω     88.00 113.00   1.00    5.00    --  108.00  45.00-150.00   25
 42  ω     54.00 120.00   1.00    5.00    --  108.00 -61.00-150.00   66
 43  ω    152.00 178.00   1.00    5.00    --  108.00  45.00  60.00   26
 44  ω     88.00 121.00   1.00    5.00    --  108.00  61.00-120.00   33
 45  ω     38.00  99.00   1.00    5.00    --  108.00 -94.00 -30.00   61
 46  ω     88.00 113.00   1.00    5.00    --  108.00  45.00 -60.00   25
 47  ω    127.00 153.00   1.00    5.00    --  108.00  45.00 -60.00   26
 48  ω     98.00 138.00   1.00    5.00    --  108.00  45.00  60.00   40
 49  ω     88.00 159.00   1.00    5.00    --  108.00  61.00   0.00   71
 50  ω     88.00 122.00   1.00    5.00    --  108.00  45.00 120.00   34
 51  ω    139.00 176.00   1.00    5.00    --  108.00  45.00 150.00   37
 52  ω     88.00 114.00   1.00    5.00    --  108.00  45.00 150.00   26
 53  ω     88.00 116.00   1.00    5.00    --  108.00  61.00  90.00   28
 54  ω     88.00 164.00   1.00    5.00    --  108.00  61.00 -30.00   76
 55  ω     89.00 127.00   1.00    5.00    --  108.00  45.00 -30.00   38
 56  ω     88.00 119.00   1.00    5.00    --  108.00  45.00   0.00   31
 57  ω     89.00 158.00   1.00    5.00    --  108.00  61.00 -60.00   69
 58  ω     88.00 120.00   1.00    5.00    --  108.00  61.00 120.00   32
 59  ω    126.00 176.00   1.00    5.00    --  108.00  61.00 120.00   50
 60  ω     89.00 115.00   1.00    5.00    --  108.00  61.00 150.00   26
 61  ω     88.00 114.00   1.00    5.00    --  108.00  61.00-180.00   26
 62  ω     89.00 122.00   1.00    5.00    --  108.00  61.00 -90.00   33
 63  ω     89.00 115.00   1.00    5.00    --  108.00  45.00 -90.00   26
 64  ω     89.00 117.00   1.00    5.00    --  108.00  45.00-120.00   28
 65  ω    145.00 175.00   1.00    5.00    --  108.00  45.00  90.00   30
 66  ω     38.00  67.00   1.00    5.00    --  108.00 -94.00  30.00   29
 67  ω    122.00 175.00   1.00    5.00    --  108.00  77.00-150.00   53
 68  ω     88.00 114.00   1.00    5.00    --  108.00  45.00  90.00   26
 69  ω     88.00 114.00   1.00    5.00    --  108.00  61.00  30.00   26
 70  ω     82.00 110.00   1.00    5.00    --  108.00  30.00  60.00   28
 71  ω     88.00 113.00   1.00    5.00    --  108.00  61.00-150.00   25
 72  ω     46.00  84.00   1.00    1.00    --   72.00  73.00-178.87   38
;
_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      -0.0091633000
_diffrn_orient_matrix_UB_12      0.0082395000
_diffrn_orient_matrix_UB_13      -0.0526798000
_diffrn_orient_matrix_UB_21      0.1546336500
_diffrn_orient_matrix_UB_22      -0.0066999500
_diffrn_orient_matrix_UB_23      0.0046410000
_diffrn_orient_matrix_UB_31      -0.0072825500
_diffrn_orient_matrix_UB_32      -0.1530143500
_diffrn_orient_matrix_UB_33      -0.0030364000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.972
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                4992
_reflns_number_total             5491
_reflns_odcompleteness_completeness 99.86
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 2094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5491
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.025
_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)+(0.1203P)²+3.1277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2079
_refine_ls_wR_factor_ref         0.2126
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C1'(H1'), C2'(H2'), C3'(H3'),
  C4'(H4'), C7'(H7'), C8'(H8'), C11'(H11'), C12'(H12'), C14'(H14'), C15'(H15'),
 C18'(H18'), C19'(H19'), C20'(H20'), C21'(H21')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.4667(7) 0.5713(7) 0.5765(2) 0.0644(16) Uani 1 1 d . . . . .
H1 H 0.5486 0.5319 0.5735 0.077 Uiso 1 1 calc R . . . .
C2 C 0.3777(8) 0.5993(8) 0.5377(3) 0.0748(19) Uani 1 1 d . . . . .
H2 H 0.3990 0.5779 0.5088 0.090 Uiso 1 1 calc R . . . .
C3 C 0.2549(8) 0.6602(8) 0.5416(2) 0.075(2) Uani 1 1 d . . . . .
H3 H 0.1944 0.6800 0.5154 0.090 Uiso 1 1 calc R . . . .
C4 C 0.2238(7) 0.6906(7) 0.5840(2) 0.0642(16) Uani 1 1 d . . . . .
H4 H 0.1413 0.7298 0.5863 0.077 Uiso 1 1 calc R . . . .
C5 C 0.3122(6) 0.6642(6) 0.6232(2) 0.0528(13) Uani 1 1 d . . . . .
C6 C 0.4381(6) 0.6002(6) 0.6203(2) 0.0565(14) Uani 1 1 d . . . . .
C7 C 0.5251(6) 0.5710(6) 0.6618(2) 0.0543(13) Uani 1 1 d . . . . .
H7 H 0.6061 0.5278 0.6599 0.065 Uiso 1 1 calc R . . . .
C8 C 0.4962(6) 0.6024(6) 0.7029(2) 0.0571(14) Uani 1 1 d . . . . .
H8 H 0.5566 0.5825 0.7292 0.069 Uiso 1 1 calc R . . . .
C9 C 0.3723(5) 0.6666(5) 0.7068(2) 0.0491(12) Uani 1 1 d . . . . .
C10 C 0.3104(6) 0.7178(5) 0.7431(2) 0.0514(13) Uani 1 1 d . . . . .
C11 C 0.1914(6) 0.7743(6) 0.7201(2) 0.0582(15) Uani 1 1 d . . . . .
H11 H 0.1288 0.8168 0.7355 0.070 Uiso 1 1 calc R . . . .
C12 C 0.4264(6) 0.6023(6) 0.8127(2) 0.0516(13) Uani 1 1 d . . . . .
H12 H 0.4433 0.5306 0.7944 0.062 Uiso 1 1 calc R . . . .
C13 C 0.3561(6) 0.7117(5) 0.7923(2) 0.0515(13) Uani 1 1 d . . . . .
C14 C 0.3305(6) 0.8178(6) 0.8212(2) 0.0583(15) Uani 1 1 d . . . . .
H14 H 0.2833 0.8917 0.8084 0.070 Uiso 1 1 calc R . . . .
C15 C 0.3728(7) 0.8150(6) 0.8672(2) 0.0607(15) Uani 1 1 d . . . . .
H15 H 0.3532 0.8865 0.8851 0.073 Uiso 1 1 calc R . . . .
C16 C 0.4467(6) 0.7048(6) 0.8886(2) 0.0547(14) Uani 1 1 d . . . . .
C17 C 0.4726(6) 0.5972(6) 0.8603(2) 0.0518(13) Uani 1 1 d . . . . .
C18 C 0.5456(6) 0.4854(6) 0.8810(2) 0.0582(15) Uani 1 1 d . . . . .
H18 H 0.5658 0.4145 0.8629 0.070 Uiso 1 1 calc R . . . .
C19 C 0.5852(7) 0.4831(8) 0.9270(2) 0.0684(17) Uani 1 1 d . . . . .
H19 H 0.6309 0.4090 0.9403 0.082 Uiso 1 1 calc R . . . .
C20 C 0.5591(8) 0.5898(9) 0.9550(2) 0.074(2) Uani 1 1 d . . . . .
H20 H 0.5884 0.5869 0.9865 0.088 Uiso 1 1 calc R . . . .
C21 C 0.4905(7) 0.6980(8) 0.9358(2) 0.0651(17) Uani 1 1 d . . . . .
H21 H 0.4726 0.7684 0.9546 0.078 Uiso 1 1 calc R . . . .
N1 N 0.2877(5) 0.6955(5) 0.66688(18) 0.0523(11) Uani 1 1 d . . . . .
N2 N 0.1754(5) 0.7624(6) 0.6749(2) 0.0621(13) Uani 1 1 d . . . . .
C1' C 0.4031(7) 0.9861(8) 0.0751(2) 0.0646(16) Uani 1 1 d . . . . .
H1' H 0.4439 1.0680 0.0719 0.077 Uiso 1 1 calc R . . . .
C2' C 0.3546(8) 0.9150(9) 0.0369(2) 0.0739(19) Uani 1 1 d . . . . .
H2' H 0.3596 0.9497 0.0079 0.089 Uiso 1 1 calc R . . . .
C3' C 0.2970(8) 0.7893(9) 0.0413(2) 0.078(2) Uani 1 1 d . . . . .
H3' H 0.2660 0.7396 0.0152 0.093 Uiso 1 1 calc R . . . .
C4' C 0.2864(7) 0.7403(7) 0.0836(2) 0.0639(16) Uani 1 1 d . . . . .
H4' H 0.2476 0.6571 0.0862 0.077 Uiso 1 1 calc R . . . .
C5' C 0.3319(5) 0.8114(6) 0.1227(2) 0.0506(12) Uani 1 1 d . . . . .
C6' C 0.3929(6) 0.9381(6) 0.1196(2) 0.0548(14) Uani 1 1 d . . . . .
C7' C 0.4420(6) 1.0096(6) 0.1608(2) 0.0576(14) Uani 1 1 d . . . . .
H7' H 0.4847 1.0911 0.1588 0.069 Uiso 1 1 calc R . . . .
C8' C 0.4273(6) 0.9605(6) 0.2022(2) 0.0572(14) Uani 1 1 d . . . . .
H8' H 0.4585 1.0091 0.2285 0.069 Uiso 1 1 calc R . . . .
C9' C 0.3653(5) 0.8361(6) 0.2062(2) 0.0524(13) Uani 1 1 d . . . . .
C10' C 0.3310(5) 0.7604(6) 0.2427(2) 0.0545(14) Uani 1 1 d . . . . .
C11' C 0.2645(6) 0.6499(6) 0.2198(2) 0.0573(14) Uani 1 1 d . . . . .
H11' H 0.2294 0.5806 0.2353 0.069 Uiso 1 1 calc R . . . .
C12' C 0.4776(6) 0.8444(6) 0.3122(2) 0.0522(13) Uani 1 1 d . . . . .
H12' H 0.5415 0.8695 0.2940 0.063 Uiso 1 1 calc R . . . .
C13' C 0.3601(5) 0.7847(6) 0.2917(2) 0.0513(13) Uani 1 1 d . . . . .
C14' C 0.2655(6) 0.7444(7) 0.3209(2) 0.0591(15) Uani 1 1 d . . . . .
H14' H 0.1856 0.7038 0.3080 0.071 Uiso 1 1 calc R . . . .
C15' C 0.2895(6) 0.7637(7) 0.3669(2) 0.0623(16) Uani 1 1 d . . . . .
H15' H 0.2270 0.7340 0.3849 0.075 Uiso 1 1 calc R . . . .
C16' C 0.4089(6) 0.8289(6) 0.3882(2) 0.0553(14) Uani 1 1 d . . . . .
C17' C 0.5032(5) 0.8682(6) 0.3597(2) 0.0525(13) Uani 1 1 d . . . . .
C18' C 0.6232(6) 0.9318(7) 0.3806(2) 0.0612(15) Uani 1 1 d . . . . .
H18' H 0.6863 0.9606 0.3626 0.073 Uiso 1 1 calc R . . . .
C19' C 0.6455(7) 0.9502(8) 0.4266(2) 0.0691(18) Uani 1 1 d . . . . .
H19' H 0.7258 0.9899 0.4398 0.083 Uiso 1 1 calc R . . . .
C20' C 0.5546(8) 0.9127(9) 0.4548(2) 0.076(2) Uani 1 1 d . . . . .
H20' H 0.5725 0.9286 0.4863 0.091 Uiso 1 1 calc R . . . .
C21' C 0.4360(7) 0.8511(7) 0.4359(2) 0.0658(17) Uani 1 1 d . . . . .
H21' H 0.3743 0.8244 0.4547 0.079 Uiso 1 1 calc R . . . .
N1' N 0.3201(4) 0.7681(5) 0.16659(17) 0.0512(11) Uani 1 1 d . . . . .
N2' N 0.2565(5) 0.6534(5) 0.17475(19) 0.0596(13) 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
C1 C2 1.370(10) . ?
C1 C6 1.393(9) . ?
C2 C3 1.397(12) . ?
C3 C4 1.363(10) . ?
C4 C5 1.373(9) . ?
C5 C6 1.432(9) . ?
C5 N1 1.381(8) . ?
C6 C7 1.420(8) . ?
C7 C8 1.325(9) . ?
C8 C9 1.421(9) . ?
C9 C10 1.411(8) . ?
C9 N1 1.374(7) . ?
C10 C11 1.404(9) . ?
C10 C13 1.452(8) . ?
C11 N2 1.321(8) . ?
C12 C13 1.393(8) . ?
C12 C17 1.410(9) . ?
C13 C14 1.411(9) . ?
C14 C15 1.355(9) . ?
C15 C16 1.426(10) . ?
C16 C17 1.411(8) . ?
C16 C21 1.395(9) . ?
C17 C18 1.427(9) . ?
C18 C19 1.353(9) . ?
C19 C20 1.400(11) . ?
C20 C21 1.363(11) . ?
N1 N2 1.364(7) . ?
C1' C2' 1.359(10) . ?
C1' C6' 1.412(9) . ?
C2' C3' 1.403(12) . ?
C3' C4' 1.358(10) . ?
C4' C5' 1.372(9) . ?
C5' C6' 1.421(9) . ?
C5' N1' 1.384(8) . ?
C6' C7' 1.432(9) . ?
C7' C8' 1.342(9) . ?
C8' C9' 1.409(9) . ?
C9' C10' 1.400(9) . ?
C9' N1' 1.368(8) . ?
C10' C11' 1.413(9) . ?
C10' C13' 1.450(9) . ?
C11' N2' 1.317(8) . ?
C12' C13' 1.379(8) . ?
C12' C17' 1.404(8) . ?
C13' C14' 1.430(8) . ?
C14' C15' 1.350(9) . ?
C15' C16' 1.427(10) . ?
C16' C17' 1.410(8) . ?
C16' C21' 1.408(9) . ?
C17' C18' 1.420(9) . ?
C18' C19' 1.352(9) . ?
C19' C20' 1.374(12) . ?
C20' C21' 1.383(11) . ?
N1' N2' 1.357(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.0(7) . . ?
C1 C2 C3 119.7(7) . . ?
C4 C3 C2 120.0(7) . . ?
C3 C4 C5 121.1(7) . . ?
C4 C5 C6 120.3(6) . . ?
C4 C5 N1 123.8(6) . . ?
N1 C5 C6 115.9(5) . . ?
C1 C6 C5 116.9(6) . . ?
C1 C6 C7 124.4(6) . . ?
C7 C6 C5 118.7(6) . . ?
C8 C7 C6 122.9(6) . . ?
C7 C8 C9 119.7(6) . . ?
C10 C9 C8 135.7(6) . . ?
N1 C9 C8 117.7(5) . . ?
N1 C9 C10 106.5(5) . . ?
C9 C10 C13 129.0(5) . . ?
C11 C10 C9 102.8(5) . . ?
C11 C10 C13 128.1(6) . . ?
N2 C11 C10 114.5(5) . . ?
C13 C12 C17 121.9(5) . . ?
C12 C13 C10 121.8(5) . . ?
C12 C13 C14 117.5(6) . . ?
C14 C13 C10 120.7(5) . . ?
C15 C14 C13 121.9(6) . . ?
C14 C15 C16 121.5(6) . . ?
C17 C16 C15 117.6(5) . . ?
C21 C16 C15 123.0(6) . . ?
C21 C16 C17 119.4(6) . . ?
C12 C17 C16 119.7(6) . . ?
C12 C17 C18 121.6(5) . . ?
C16 C17 C18 118.7(6) . . ?
C19 C18 C17 119.7(6) . . ?
C18 C19 C20 121.4(7) . . ?
C21 C20 C19 119.7(7) . . ?
C20 C21 C16 121.0(7) . . ?
C9 N1 C5 125.1(5) . . ?
N2 N1 C5 122.7(5) . . ?
N2 N1 C9 112.2(5) . . ?
C11 N2 N1 103.9(5) . . ?
C2' C1' C6' 121.3(7) . . ?
C1' C2' C3' 119.9(7) . . ?
C4' C3' C2' 120.0(7) . . ?
C3' C4' C5' 121.1(7) . . ?
C4' C5' C6' 120.4(6) . . ?
C4' C5' N1' 123.6(6) . . ?
N1' C5' C6' 116.0(5) . . ?
C1' C6' C5' 117.2(6) . . ?
C1' C6' C7' 123.3(6) . . ?
C5' C6' C7' 119.5(6) . . ?
C8' C7' C6' 120.8(6) . . ?
C7' C8' C9' 120.8(6) . . ?
C10' C9' C8' 135.1(6) . . ?
N1' C9' C8' 117.8(5) . . ?
N1' C9' C10' 107.1(5) . . ?
C9' C10' C11' 102.4(5) . . ?
C9' C10' C13' 129.5(6) . . ?
C11' C10' C13' 128.1(6) . . ?
N2' C11' C10' 114.3(5) . . ?
C13' C12' C17' 121.8(5) . . ?
C12' C13' C10' 122.6(5) . . ?
C12' C13' C14' 117.6(6) . . ?
C14' C13' C10' 119.8(5) . . ?
C15' C14' C13' 121.6(6) . . ?
C14' C15' C16' 121.2(6) . . ?
C17' C16' C15' 117.6(6) . . ?
C21' C16' C15' 122.4(6) . . ?
C21' C16' C17' 120.0(6) . . ?
C12' C17' C16' 120.2(5) . . ?
C12' C17' C18' 121.7(5) . . ?
C16' C17' C18' 118.1(6) . . ?
C19' C18' C17' 119.9(6) . . ?
C18' C19' C20' 122.7(7) . . ?
C19' C20' C21' 119.4(7) . . ?
C20' C21' C16' 119.9(7) . . ?
C9' N1' C5' 125.0(5) . . ?
N2' N1' C5' 122.7(5) . . ?
N2' N1' C9' 112.3(5) . . ?
C11' N2' N1' 103.9(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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.839
