# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_cs046
_database_code_depnum_ccdc_archive 'CCDC 2226036'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2022-12-12 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-10-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N2'
_chemical_formula_sum            'C20 H18 N2'
_chemical_formula_weight         286.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H18 N2'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.54957(13)
_cell_length_b                   5.45668(4)
_cell_length_c                   21.5051(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.0457(10)
_cell_angle_gamma                90
_cell_volume                     1450.07(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21005
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.8430
_cell_measurement_theta_min      3.5330
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -1 -1 0.0985
-2 -1 14 0.0965
0 0 -14 0.0667
7 2 -5 0.0597
-1 3 6 0.0794
4 -3 1 0.1209
-2 -2 -10 0.0955
-5 1 -10 0.0815
3 2 11 0.0859
5 0 10 0.0982
2 -2 -12 0.1083
-8 1 -1 0.1062
-6 2 8 0.1197
8 -1 -2 0.1173
8 -1 1 0.1016
-6 -1 -7 0.0731
-2 -2 12 0.0886
-6 -2 -1 0.0827
-6 -1 -6 0.0726
3 3 -8 0.0763

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
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
-7.4588 -1.0981 -1.2917 -0.6683 0.2370 -0.7051
-2.4638 -0.6642 13.5826 -0.7260 0.2558 0.6383
-0.4334 0.2266 -13.5693 0.4478 -0.1572 -0.8802
6.7092 1.8704 -4.8490 0.9509 -0.1249 0.2833
-1.0356 3.2156 5.7952 0.3087 0.8721 0.3798
3.7268 -3.1030 0.9785 -0.3211 -0.9099 0.2624
-1.7839 -2.1720 -9.8971 -0.1874 -0.5267 -0.8291
-4.6174 0.5295 -9.7588 0.0887 0.2551 -0.9628
2.6092 1.6537 10.5493 0.1320 0.3697 0.9197
4.5990 -0.4918 9.8117 -0.0851 -0.2448 0.9658
2.3430 -1.5344 -12.4393 0.2928 -0.7079 -0.6428
-7.5407 1.0978 -0.7337 -0.3046 0.7316 -0.6099
-6.2753 1.6937 7.6707 -0.3830 0.9230 0.0366
7.5078 -1.3748 -2.2606 0.3500 -0.8419 0.4107
7.5447 -1.1050 0.6631 0.3058 -0.7347 0.6055
-6.0128 -0.7658 -6.9892 -0.3258 0.1138 -0.9386
-1.7484 -1.7884 12.0160 -0.8243 -0.0648 0.5624
-6.2788 -2.1277 -1.0401 -0.7764 -0.0624 -0.6271
-5.7163 -1.4043 -6.4287 -0.4360 -0.0357 -0.8992
2.5383 2.7161 -8.4725 0.9283 0.2760 -0.2490

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            38566
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.787
_diffrn_reflns_theta_min         3.814
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  90.00  101
  2  ω    -87.00  -6.00   1.00    1.00    --  -41.68 125.00 -60.00   81
  3  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-180.00  101
  4  ω      6.00  83.00   1.00    1.00    --   41.68 -99.00-120.00   77
  5  ω    -21.00  74.00   1.00    1.00    --   41.68 -77.00 -60.00   95
  6  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00-120.00   84
  7  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00 -30.00   84
  8  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00  30.00   84
  9  ω     34.00 135.00   1.00    2.00    --  106.01 -61.00   0.00  101
 10  ω    103.00 178.00   1.00    2.00    --  106.01  77.00   0.00   75
 11  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00-180.00   84
 12  ω     34.00 135.00   1.00    2.00    --  106.01 -61.00-180.00  101
 13  ω     33.00 112.00   1.00    2.00    --  106.01-125.00-180.00   79
 14  ω     78.00 178.00   1.00    2.00    --  106.01  30.00 -30.00  100
 15  ω     30.00 134.00   1.00    2.00    --  106.01 -30.00 150.00  104
 16  ω     24.00 159.00   1.00    2.00    --  106.01 -15.00 -60.00  135
 17  ω    -87.00  -6.00   1.00    1.00    --  -41.68 125.00  30.00   81
 18  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  30.00  101
 19  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -30.00  101
 20  ω   -115.00 -59.00   1.00    1.00    --  -41.68-152.00  29.00   56
 21  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -90.00  101
 22  ω     77.00 178.00   1.00    2.00    --  106.01  61.00-180.00  101
 23  ω     77.00 178.00   1.00    2.00    --  106.01  61.00  60.00  101
 24  ω     78.00 178.00   1.00    2.00    --  106.01  30.00 120.00  100
 25  ω     80.00 178.00   1.00    2.00    --  106.01  45.00 150.00   98
 26  ω     77.00 178.00   1.00    2.00    --  106.01  61.00   0.00  101
 27  ω     77.00 178.00   1.00    2.00    --  106.01  61.00-120.00  101
 28  ω     77.00 178.00   1.00    2.00    --  106.01  61.00 -90.00  101
 29  ω     77.00 178.00   1.00    2.00    --  106.01  61.00-150.00  101
 30  ω     77.00 178.00   1.00    2.00    --  106.01  61.00 -30.00  101
 31  ω     77.00 178.00   1.00    2.00    --  106.01  61.00  30.00  101
 32  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-150.00  101
 33  ω     14.00 115.00   1.00    1.00    --   41.68  57.00-120.00  101
 34  ω     17.00 116.00   1.00    1.00    --   41.68  40.00  48.00   99
 35  ω     17.00 116.00   1.00    1.00    --   41.68  38.00-180.00   99
 36  ω     17.00 116.00   1.00    1.00    --   41.68  38.00 150.00   99
 37  ω     77.00 178.00   1.00    2.00    --  106.01  61.00 150.00  101
 38  ω     80.00 178.00   1.00    2.00    --  106.01  45.00  60.00   98
 39  ω     80.00 178.00   1.00    2.00    --  106.01  45.00 120.00   98
 40  ω     80.00 178.00   1.00    2.00    --  106.01  45.00  30.00   98
 41  ω     77.00 178.00   1.00    2.00    --  106.01  61.00  90.00  101
 42  ω     77.00 178.00   1.00    2.00    --  106.01  61.00 120.00  101
 43  ω     80.00 178.00   1.00    2.00    --  106.01  45.00-180.00   98
 44  ω     80.00 178.00   1.00    2.00    --  106.01  45.00 -90.00   98
 45  ω     80.00 178.00   1.00    2.00    --  106.01  45.00-150.00   98
 46  ω     77.00 178.00   1.00    2.00    --  106.01  61.00 -60.00  101
 47  ω      1.00  52.00   1.00    1.00    --   41.68  19.00 -90.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0692146000
_diffrn_orient_matrix_UB_12      0.1764478000
_diffrn_orient_matrix_UB_13      -0.0322680000
_diffrn_orient_matrix_UB_21      -0.0669285000
_diffrn_orient_matrix_UB_22      0.2183392000
_diffrn_orient_matrix_UB_23      0.0173680000
_diffrn_orient_matrix_UB_31      0.0791813000
_diffrn_orient_matrix_UB_32      0.0303453000
_diffrn_orient_matrix_UB_33      0.0628439000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2686
_reflns_number_total             2917
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.040
_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)+(0.0535P)²+0.4333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_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
N1 N 0.70164(7) 0.51243(17) 0.54383(4) 0.0211(2) Uani 1 1 d . . . . .
N2 N 0.83115(7) 0.86464(16) 0.50316(4) 0.0191(2) Uani 1 1 d . . . . .
C1 C 0.72061(8) 0.49727(18) 0.47910(5) 0.0184(2) Uani 1 1 d . . . . .
H1A H 0.725911 0.319883 0.468366 0.022 Uiso 1 1 calc R U . . .
C2 C 0.75093(8) 0.68496(18) 0.58647(5) 0.0182(2) Uani 1 1 d . . . . .
C3 C 0.73548(8) 0.68392(19) 0.64927(5) 0.0207(2) Uani 1 1 d . . . . .
H3 H 0.693725 0.557391 0.663601 0.025 Uiso 1 1 calc R U . . .
C4 C 0.78041(8) 0.8656(2) 0.69101(5) 0.0219(2) Uani 1 1 d . . . . .
H4 H 0.769092 0.862541 0.733544 0.026 Uiso 1 1 calc R U . . .
C5 C 0.84191(8) 1.05193(19) 0.67081(5) 0.0216(2) Uani 1 1 d . . . . .
H5 H 0.870991 1.178687 0.699024 0.026 Uiso 1 1 calc R U . . .
C6 C 0.86041(8) 1.05080(19) 0.60885(5) 0.0201(2) Uani 1 1 d . . . . .
H6 H 0.903887 1.175443 0.595191 0.024 Uiso 1 1 calc R U . . .
C7 C 0.81610(8) 0.86968(18) 0.56670(5) 0.0179(2) Uani 1 1 d . . . . .
C8 C 0.83223(8) 0.61810(18) 0.47638(5) 0.0183(2) Uani 1 1 d . . . . .
H8 H 0.889551 0.520636 0.503798 0.022 Uiso 1 1 calc R U . . .
C9 C 0.85910(8) 0.62588(18) 0.41065(5) 0.0182(2) Uani 1 1 d . . . . .
C10 C 0.92076(8) 0.43825(19) 0.39083(5) 0.0201(2) Uani 1 1 d . . . . .
H10 H 0.947707 0.310955 0.419434 0.024 Uiso 1 1 calc R U . . .
C11 C 0.94337(9) 0.4348(2) 0.32984(5) 0.0231(2) Uani 1 1 d . . . . .
H11 H 0.985654 0.306148 0.316949 0.028 Uiso 1 1 calc R U . . .
H1 H 0.6691(11) 0.393(3) 0.5581(6) 0.028 Uiso 1 1 d . U . . .
H2 H 0.8863(11) 0.956(3) 0.4956(6) 0.028 Uiso 1 1 d . U . . .
C12 C 0.90399(8) 0.6198(2) 0.28785(5) 0.0229(2) Uani 1 1 d . . . . .
H12 H 0.918140 0.616492 0.245874 0.027 Uiso 1 1 calc R U . . .
C13 C 0.84384(8) 0.8101(2) 0.30718(5) 0.0223(2) Uani 1 1 d . . . . .
H13 H 0.817939 0.938264 0.278607 0.027 Uiso 1 1 calc R U . . .
C14 C 0.82148(8) 0.81343(19) 0.36818(5) 0.0203(2) Uani 1 1 d . . . . .
H14 H 0.780342 0.944058 0.381136 0.024 Uiso 1 1 calc R U . . .
C15 C 0.63016(8) 0.60866(18) 0.43152(5) 0.0180(2) Uani 1 1 d . . . . .
C16 C 0.60357(8) 0.50524(19) 0.37158(5) 0.0208(2) Uani 1 1 d . . . . .
H16 H 0.639040 0.359874 0.361937 0.025 Uiso 1 1 calc R U . . .
C17 C 0.52577(8) 0.6123(2) 0.32575(5) 0.0235(2) Uani 1 1 d . . . . .
H17 H 0.508487 0.540390 0.285005 0.028 Uiso 1 1 calc R U . . .
C18 C 0.47333(8) 0.8241(2) 0.33942(5) 0.0236(2) Uani 1 1 d . . . . .
H18 H 0.420626 0.898282 0.307986 0.028 Uiso 1 1 calc R U . . .
C19 C 0.49812(8) 0.9275(2) 0.39929(5) 0.0233(2) Uani 1 1 d . . . . .
H19 H 0.461796 1.071662 0.408912 0.028 Uiso 1 1 calc R U . . .
C20 C 0.57606(8) 0.82009(19) 0.44510(5) 0.0207(2) Uani 1 1 d . . . . .
H20 H 0.592576 0.891261 0.485965 0.025 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
N1 C1 1.4549(12) . ?
N1 C2 1.3827(13) . ?
N1 H1 0.855(15) . ?
N2 C7 1.4119(13) . ?
N2 C8 1.4644(13) . ?
N2 H2 0.893(15) . ?
C1 H1A 1.0000 . ?
C1 C8 1.5585(14) . ?
C1 C15 1.5164(14) . ?
C2 C3 1.3976(14) . ?
C2 C7 1.4096(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3891(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3912(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3919(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.3899(14) . ?
C8 H8 1.0000 . ?
C8 C9 1.5100(13) . ?
C9 C10 1.3942(14) . ?
C9 C14 1.3978(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3898(14) . ?
C11 H11 0.9500 . ?
C11 C12 1.3869(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3894(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3885(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.3934(14) . ?
C15 C20 1.3951(14) . ?
C16 H16 0.9500 . ?
C16 C17 1.3894(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.3864(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3903(16) . ?
C19 H19 0.9500 . ?
C19 C20 1.3909(15) . ?
C20 H20 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
C1 N1 H1 117.9(9) . . ?
C2 N1 C1 122.98(8) . . ?
C2 N1 H1 117.9(9) . . ?
C7 N2 C8 114.24(8) . . ?
C7 N2 H2 113.9(9) . . ?
C8 N2 H2 112.5(9) . . ?
N1 C1 H1A 107.7 . . ?
N1 C1 C8 108.05(8) . . ?
N1 C1 C15 113.24(8) . . ?
C8 C1 H1A 107.7 . . ?
C15 C1 H1A 107.7 . . ?
C15 C1 C8 112.15(8) . . ?
N1 C2 C3 121.11(9) . . ?
N1 C2 C7 120.19(9) . . ?
C3 C2 C7 118.68(9) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.83(9) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.31(9) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.34(10) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.86(9) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 N2 117.42(9) . . ?
C6 C7 N2 122.62(9) . . ?
C6 C7 C2 119.94(9) . . ?
N2 C8 C1 107.69(8) . . ?
N2 C8 H8 108.2 . . ?
N2 C8 C9 111.18(8) . . ?
C1 C8 H8 108.2 . . ?
C9 C8 C1 113.32(8) . . ?
C9 C8 H8 108.2 . . ?
C10 C9 C8 119.47(9) . . ?
C10 C9 C14 118.70(9) . . ?
C14 C9 C8 121.81(9) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.93(9) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.77(9) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.98(10) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.15(10) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.46(9) . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C1 119.48(9) . . ?
C16 C15 C20 118.80(9) . . ?
C20 C15 C1 121.64(9) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.74(10) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.06(10) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.79(10) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.07(10) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.53(10) . . ?
C19 C20 H20 119.7 . . ?

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
N1 C1 C8 N2 -53.64(10) . . . . ?
N1 C1 C8 C9 -177.04(8) . . . . ?
N1 C1 C15 C16 -145.76(9) . . . . ?
N1 C1 C15 C20 37.44(13) . . . . ?
N1 C2 C3 C4 -176.46(9) . . . . ?
N1 C2 C7 N2 -2.08(14) . . . . ?
N1 C2 C7 C6 176.34(9) . . . . ?
N2 C8 C9 C10 144.49(9) . . . . ?
N2 C8 C9 C14 -37.18(13) . . . . ?
C1 N1 C2 C3 -176.13(9) . . . . ?
C1 N1 C2 C7 5.36(15) . . . . ?
C1 C8 C9 C10 -94.05(11) . . . . ?
C1 C8 C9 C14 84.28(11) . . . . ?
C1 C15 C16 C17 -175.94(9) . . . . ?
C1 C15 C20 C19 175.89(9) . . . . ?
C2 N1 C1 C8 23.24(12) . . . . ?
C2 N1 C1 C15 -101.63(11) . . . . ?
C2 C3 C4 C5 -0.11(15) . . . . ?
C3 C2 C7 N2 179.37(8) . . . . ?
C3 C2 C7 C6 -2.21(14) . . . . ?
C3 C4 C5 C6 -1.74(15) . . . . ?
C4 C5 C6 C7 1.58(15) . . . . ?
C5 C6 C7 N2 178.73(9) . . . . ?
C5 C6 C7 C2 0.40(15) . . . . ?
C7 N2 C8 C1 60.66(10) . . . . ?
C7 N2 C8 C9 -174.64(8) . . . . ?
C7 C2 C3 C4 2.07(14) . . . . ?
C8 N2 C7 C2 -32.62(12) . . . . ?
C8 N2 C7 C6 149.01(10) . . . . ?
C8 C1 C15 C16 91.62(11) . . . . ?
C8 C1 C15 C20 -85.17(11) . . . . ?
C8 C9 C10 C11 177.47(9) . . . . ?
C8 C9 C14 C13 -177.33(9) . . . . ?
C9 C10 C11 C12 -0.17(15) . . . . ?
C10 C9 C14 C13 1.01(15) . . . . ?
C10 C11 C12 C13 1.17(16) . . . . ?
C11 C12 C13 C14 -1.07(16) . . . . ?
C12 C13 C14 C9 -0.03(15) . . . . ?
C14 C9 C10 C11 -0.91(15) . . . . ?
C15 C1 C8 N2 71.87(10) . . . . ?
C15 C1 C8 C9 -51.53(11) . . . . ?
C15 C16 C17 C18 -0.19(16) . . . . ?
C16 C15 C20 C19 -0.93(15) . . . . ?
C16 C17 C18 C19 -0.61(16) . . . . ?
C17 C18 C19 C20 0.63(16) . . . . ?
C18 C19 C20 C15 0.15(15) . . . . ?
C20 C15 C16 C17 0.95(15) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.315
_oxdiff_exptl_absorpt_empirical_full_min 0.754

