# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_202105142
_database_code_depnum_ccdc_archive 'CCDC 2106532'
loop_
_audit_author_name
_audit_author_address
ketiwu
;ZhengZhou University
China
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_audit_creation_date             2021-05-26
_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         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O5N2
_chemical_oxdiff_usercomment     r
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           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                   16.3920(6)
_cell_length_b                   7.1332(4)
_cell_length_c                   20.1084(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.662(4)
_cell_angle_gamma                90
_cell_volume                     2339.77(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2314
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8070
_cell_measurement_theta_min      4.4000
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8634
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         3.322
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00 -22.00   1.00    1.50    --  -33.50 -77.00-180.00   27
  2  ω    -98.00 -33.00   1.00    1.50    --  -33.50 178.00-180.00   65
  3  ω      8.00  35.00   1.00    1.50    --  -33.50  37.00 150.00   27
  4  ω      4.00  33.00   1.00    1.50    --  -33.50  57.00  60.00   29
  5  ω    -55.00 -22.00   1.00    1.50    --  -33.50  37.00 150.00   33
  6  ω    -34.00  56.00   1.00    1.50    --   36.47 -37.00  90.00   90
  7  ω     25.00  50.00   1.00    1.50    --   36.47 -57.00-120.00   25
  8  ω     41.00  76.00   1.00    1.50    --   36.47 -99.00-180.00   35
  9  ω     29.00  70.00   1.00    1.50    --   36.47 -99.00 120.00   41
 10  ω     -3.00  23.00   1.00    1.50    --   36.47 -99.00 120.00   26
 11  ω    -27.00  13.00   1.00    1.50    --   36.47 -57.00-120.00   40
 12  ω    120.00 146.00   1.00    6.00    --  108.00 111.00-120.00   26
 13  ω    115.00 169.00   1.00    6.00    --  108.00 111.00   0.00   54
 14  ω     51.00 111.00   1.00    6.00    --  108.00-111.00 120.00   60
 15  ω    123.00 176.00   1.00    6.00    --  108.00  77.00-150.00   53
 16  ω     73.00 106.00   1.00    6.00    --  108.00 -94.00-180.00   33
 17  ω     92.00 149.00   1.00    6.00    --  108.00  61.00-150.00   57
 18  ω    109.00 168.00   1.00    6.00    --  108.00  61.00 120.00   59
 19  ω     91.00 160.00   1.00    6.00    --  108.00  45.00-180.00   69
 20  ω     41.00 128.00   1.00    6.00    --  108.00 -61.00  90.00   87
;
_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      -0.0422225000
_diffrn_orient_matrix_UB_12      0.1933813000
_diffrn_orient_matrix_UB_13      -0.0038562000
_diffrn_orient_matrix_UB_21      -0.0841647000
_diffrn_orient_matrix_UB_22      -0.0959885000
_diffrn_orient_matrix_UB_23      -0.0004316000
_diffrn_orient_matrix_UB_31      0.0067161000
_diffrn_orient_matrix_UB_32      0.0091763000
_diffrn_orient_matrix_UB_33      0.0768810000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3055
_reflns_number_total             4191
_reflns_odcompleteness_completeness 99.87
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.045
_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)+(0.0680P)²+0.0639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1434
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C1'(H1'), C2(H2), C2'(H2'), C3(H3), C3'(H3'), C4(H4), C4'(H4'),
 C10(H10), C10'(H10'), C11(H11), C11'(H11'), C12(H12), C12'(H12'), C13(H13),
 C13'(H13'), C14(H14), C14'(H14')
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15'(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.53444(9) 0.8452(3) 0.20081(8) 0.0697(5) Uani 1 1 d . . . . .
O1' O 0.62744(11) 0.3372(3) 0.09553(8) 0.0922(7) Uani 1 1 d . . . . .
N1 N 0.33170(9) 0.7231(3) 0.23209(7) 0.0481(4) Uani 1 1 d . . . . .
N1' N 0.54999(9) 0.3578(2) 0.25425(8) 0.0470(4) Uani 1 1 d . . . . .
N2 N 0.42178(10) 0.8170(2) 0.12686(8) 0.0491(4) Uani 1 1 d . . . . .
N2' N 0.69774(10) 0.3656(2) 0.19757(9) 0.0533(4) Uani 1 1 d . . . . .
C1 C 0.29801(15) 0.7787(3) 0.04883(10) 0.0597(5) Uani 1 1 d . . . . .
H1 H 0.3254 0.8161 0.0127 0.072 Uiso 1 1 calc R . . . .
C1' C 0.77142(13) 0.3789(3) 0.30982(13) 0.0646(6) Uani 1 1 d . . . . .
H1' H 0.8220 0.3797 0.2925 0.077 Uiso 1 1 calc R . . . .
C2 C 0.21705(15) 0.7271(4) 0.03943(11) 0.0676(6) Uani 1 1 d . . . . .
H2 H 0.1900 0.7303 -0.0034 0.081 Uiso 1 1 calc R . . . .
C2' C 0.76764(15) 0.3844(4) 0.37736(14) 0.0745(7) Uani 1 1 d . . . . .
H2' H 0.8161 0.3886 0.4056 0.089 Uiso 1 1 calc R . . . .
C3 C 0.17459(14) 0.6703(4) 0.09216(11) 0.0659(6) Uani 1 1 d . . . . .
H3 H 0.1202 0.6325 0.0846 0.079 Uiso 1 1 calc R . . . .
C3' C 0.69358(16) 0.3839(4) 0.40469(12) 0.0722(7) Uani 1 1 d . . . . .
H3' H 0.6922 0.3887 0.4508 0.087 Uiso 1 1 calc R . . . .
C4 C 0.21367(12) 0.6705(4) 0.15547(10) 0.0587(6) Uani 1 1 d . . . . .
H4 H 0.1852 0.6349 0.1912 0.070 Uiso 1 1 calc R . . . .
C4' C 0.62196(14) 0.3763(3) 0.36309(10) 0.0594(5) Uani 1 1 d . . . . .
H4' H 0.5719 0.3758 0.3813 0.071 Uiso 1 1 calc R . . . .
C5 C 0.29606(11) 0.7237(3) 0.16706(9) 0.0462(4) Uani 1 1 d . . . . .
C5' C 0.62346(12) 0.3693(3) 0.29395(10) 0.0480(4) Uani 1 1 d . . . . .
C6 C 0.33897(12) 0.7748(3) 0.11312(9) 0.0464(4) Uani 1 1 d . . . . .
C6' C 0.69896(12) 0.3722(3) 0.26687(11) 0.0505(5) Uani 1 1 d . . . . .
C7 C 0.46112(11) 0.8138(3) 0.19028(10) 0.0488(5) Uani 1 1 d . . . . .
C7' C 0.62646(13) 0.3500(3) 0.15587(10) 0.0562(5) Uani 1 1 d . . . . .
C8 C 0.40851(11) 0.7677(3) 0.24396(9) 0.0445(4) Uani 1 1 d . . . . .
C8' C 0.54954(12) 0.3476(3) 0.19007(9) 0.0460(4) Uani 1 1 d . . . . .
C9 C 0.44335(11) 0.7675(3) 0.31511(9) 0.0463(4) Uani 1 1 d . . . . .
C9' C 0.46851(12) 0.3277(3) 0.15063(10) 0.0473(4) Uani 1 1 d . . . . .
C10 C 0.41052(12) 0.6432(3) 0.35879(10) 0.0538(5) Uani 1 1 d . . . . .
H10 H 0.3703 0.5584 0.3426 0.065 Uiso 1 1 calc R . . . .
C10' C 0.40202(13) 0.2700(3) 0.18434(11) 0.0566(5) Uani 1 1 d . . . . .
H10' H 0.4100 0.2463 0.2300 0.068 Uiso 1 1 calc R . . . .
C11 C 0.43741(14) 0.6453(4) 0.42620(11) 0.0634(6) Uani 1 1 d . . . . .
H11 H 0.4149 0.5626 0.4552 0.076 Uiso 1 1 calc R . . . .
C11' C 0.32527(14) 0.2480(4) 0.15127(12) 0.0658(6) Uani 1 1 d . . . . .
H11' H 0.2820 0.2089 0.1745 0.079 Uiso 1 1 calc R . . . .
C12 C 0.49748(14) 0.7697(4) 0.45050(11) 0.0674(7) Uani 1 1 d . . . . .
H12 H 0.5158 0.7704 0.4958 0.081 Uiso 1 1 calc R . . . .
C12' C 0.31230(15) 0.2837(4) 0.08369(13) 0.0707(7) Uani 1 1 d . . . . .
H12' H 0.2605 0.2670 0.0612 0.085 Uiso 1 1 calc R . . . .
C13 C 0.53031(13) 0.8926(4) 0.40768(12) 0.0647(6) Uani 1 1 d . . . . .
H13 H 0.5706 0.9768 0.4243 0.078 Uiso 1 1 calc R . . . .
C13' C 0.37612(17) 0.3441(4) 0.04961(12) 0.0721(7) Uani 1 1 d . . . . .
H13' H 0.3669 0.3707 0.0042 0.087 Uiso 1 1 calc R . . . .
C14 C 0.50395(12) 0.8923(3) 0.34041(11) 0.0566(5) Uani 1 1 d . . . . .
H14 H 0.5267 0.9757 0.3119 0.068 Uiso 1 1 calc R . . . .
C14' C 0.45417(15) 0.3658(3) 0.08243(10) 0.0599(6) Uani 1 1 d . . . . .
H14' H 0.4970 0.4059 0.0589 0.072 Uiso 1 1 calc R . . . .
C15 C 0.47141(15) 0.8623(4) 0.07230(11) 0.0689(6) Uani 1 1 d . . . . .
H15A H 0.4684 0.7610 0.0407 0.103 Uiso 1 1 calc GR . . . .
H15B H 0.5274 0.8807 0.0900 0.103 Uiso 1 1 calc GR . . . .
H15C H 0.4510 0.9748 0.0504 0.103 Uiso 1 1 calc GR . . . .
C15' C 0.77512(14) 0.3725(4) 0.16632(13) 0.0713(7) Uani 1 1 d . . . . .
H15D H 0.8043 0.4851 0.1798 0.107 Uiso 1 1 calc GR . . . .
H15E H 0.7635 0.3715 0.1186 0.107 Uiso 1 1 calc GR . . . .
H15F H 0.8080 0.2655 0.1801 0.107 Uiso 1 1 calc GR . . . .


_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 C7 1.220(2) . ?
O1' C7' 1.218(3) . ?
N1 C5 1.379(2) . ?
N1 C8 1.298(2) . ?
N1' C5' 1.380(2) . ?
N1' C8' 1.292(2) . ?
N2 C6 1.391(3) . ?
N2 C7 1.371(3) . ?
N2 C15 1.465(3) . ?
N2' C6' 1.392(3) . ?
N2' C7' 1.374(3) . ?
N2' C15' 1.471(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(3) . ?
C1 C6 1.397(3) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.366(3) . ?
C1' C6' 1.399(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.381(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(3) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(3) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.394(3) . ?
C5 C6 1.398(3) . ?
C5' C6' 1.400(3) . ?
C7 C8 1.484(3) . ?
C7' C8' 1.495(3) . ?
C8 C9 1.487(2) . ?
C8' C9' 1.485(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.392(3) . ?
C9' C10' 1.401(3) . ?
C9' C14' 1.395(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(3) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.373(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(4) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.375(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.389(3) . ?
C14 H14 0.9300 . ?
C14' H14' 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 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
C8 N1 C5 119.10(17) . . ?
C8' N1' C5' 119.99(17) . . ?
C6 N2 C15 120.13(17) . . ?
C7 N2 C6 122.77(16) . . ?
C7 N2 C15 117.07(18) . . ?
C6' N2' C15' 119.91(19) . . ?
C7' N2' C6' 122.75(16) . . ?
C7' N2' C15' 117.34(19) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C6 119.5(2) . . ?
C6 C1 H1 120.3 . . ?
C2' C1' H1' 120.1 . . ?
C2' C1' C6' 119.7(2) . . ?
C6' C1' H1' 120.1 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.7(2) . . ?
C3 C2 H2 119.2 . . ?
C1' C2' H2' 119.2 . . ?
C1' C2' C3' 121.6(2) . . ?
C3' C2' H2' 119.2 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2' C3' H3' 120.3 . . ?
C4' C3' C2' 119.3(2) . . ?
C4' C3' H3' 120.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3' C4' H4' 119.6 . . ?
C3' C4' C5' 120.7(2) . . ?
C5' C4' H4' 119.6 . . ?
N1 C5 C4 117.95(18) . . ?
N1 C5 C6 122.55(17) . . ?
C6 C5 C4 119.50(17) . . ?
N1' C5' C4' 118.60(18) . . ?
N1' C5' C6' 122.01(19) . . ?
C4' C5' C6' 119.38(19) . . ?
N2 C6 C1 123.36(19) . . ?
N2 C6 C5 117.26(17) . . ?
C1 C6 C5 119.37(19) . . ?
N2' C6' C1' 123.13(19) . . ?
N2' C6' C5' 117.56(18) . . ?
C1' C6' C5' 119.3(2) . . ?
O1 C7 N2 121.54(19) . . ?
O1 C7 C8 123.21(19) . . ?
N2 C7 C8 115.24(17) . . ?
O1' C7' N2' 121.33(19) . . ?
O1' C7' C8' 123.5(2) . . ?
N2' C7' C8' 115.18(17) . . ?
N1 C8 C7 122.93(17) . . ?
N1 C8 C9 116.76(17) . . ?
C7 C8 C9 120.30(16) . . ?
N1' C8' C7' 122.48(18) . . ?
N1' C8' C9' 117.10(17) . . ?
C9' C8' C7' 120.40(17) . . ?
C10 C9 C8 118.14(18) . . ?
C14 C9 C8 122.91(19) . . ?
C14 C9 C10 118.86(18) . . ?
C10' C9' C8' 117.84(18) . . ?
C14' C9' C8' 124.15(19) . . ?
C14' C9' C10' 118.0(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9' C10' H10' 119.4 . . ?
C11' C10' C9' 121.2(2) . . ?
C11' C10' H10' 119.4 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C10' C11' H11' 120.0 . . ?
C10' C11' C12' 120.1(2) . . ?
C12' C11' H11' 120.0 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C11' C12' H12' 120.1 . . ?
C13' C12' C11' 119.9(2) . . ?
C13' C12' H12' 120.1 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12' C13' H13' 119.7 . . ?
C12' C13' C14' 120.6(2) . . ?
C14' C13' H13' 119.7 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C9' C14' H14' 119.9 . . ?
C13' C14' C9' 120.2(2) . . ?
C13' C14' H14' 119.9 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2' C15' H15D 109.5 . . ?
N2' C15' H15E 109.5 . . ?
N2' C15' H15F 109.5 . . ?
H15D C15' H15E 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?

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
O1 C7 C8 N1 -175.6(2) . . . . ?
O1 C7 C8 C9 3.2(3) . . . . ?
O1' C7' C8' N1' 178.7(2) . . . . ?
O1' C7' C8' C9' 0.4(4) . . . . ?
N1 C5 C6 N2 3.2(3) . . . . ?
N1 C5 C6 C1 -177.7(2) . . . . ?
N1 C8 C9 C10 30.2(3) . . . . ?
N1 C8 C9 C14 -146.3(2) . . . . ?
N1' C5' C6' N2' 0.8(3) . . . . ?
N1' C5' C6' C1' -178.30(19) . . . . ?
N1' C8' C9' C10' -17.3(3) . . . . ?
N1' C8' C9' C14' 161.6(2) . . . . ?
N2 C7 C8 N1 3.7(3) . . . . ?
N2 C7 C8 C9 -177.51(18) . . . . ?
N2' C7' C8' N1' -0.6(3) . . . . ?
N2' C7' C8' C9' -178.86(18) . . . . ?
C1 C2 C3 C4 1.8(4) . . . . ?
C1' C2' C3' C4' 0.5(4) . . . . ?
C2 C1 C6 N2 177.1(2) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C2' C1' C6' N2' -179.7(2) . . . . ?
C2' C1' C6' C5' -0.6(3) . . . . ?
C2' C3' C4' C5' -0.1(4) . . . . ?
C3 C4 C5 N1 179.3(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3' C4' C5' N1' 178.7(2) . . . . ?
C3' C4' C5' C6' -0.7(4) . . . . ?
C4 C5 C6 N2 -176.7(2) . . . . ?
C4 C5 C6 C1 2.4(3) . . . . ?
C4' C5' C6' N2' -179.79(19) . . . . ?
C4' C5' C6' C1' 1.1(3) . . . . ?
C5 N1 C8 C7 -2.1(3) . . . . ?
C5 N1 C8 C9 179.08(18) . . . . ?
C5' N1' C8' C7' -0.8(3) . . . . ?
C5' N1' C8' C9' 177.56(17) . . . . ?
C6 N2 C7 O1 177.5(2) . . . . ?
C6 N2 C7 C8 -1.8(3) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C6' N2' C7' O1' -177.1(2) . . . . ?
C6' N2' C7' C8' 2.2(3) . . . . ?
C6' C1' C2' C3' -0.2(4) . . . . ?
C7 N2 C6 C1 179.5(2) . . . . ?
C7 N2 C6 C5 -1.4(3) . . . . ?
C7 C8 C9 C10 -148.70(19) . . . . ?
C7 C8 C9 C14 34.8(3) . . . . ?
C7' N2' C6' C1' 176.8(2) . . . . ?
C7' N2' C6' C5' -2.3(3) . . . . ?
C7' C8' C9' C10' 161.1(2) . . . . ?
C7' C8' C9' C14' -20.0(3) . . . . ?
C8 N1 C5 C4 178.4(2) . . . . ?
C8 N1 C5 C6 -1.5(3) . . . . ?
C8 C9 C10 C11 -176.16(19) . . . . ?
C8 C9 C14 C13 176.1(2) . . . . ?
C8' N1' C5' C4' -178.7(2) . . . . ?
C8' N1' C5' C6' 0.7(3) . . . . ?
C8' C9' C10' C11' -179.8(2) . . . . ?
C8' C9' C14' C13' -179.7(2) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9' C10' C11' C12' -0.4(4) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C10' C9' C14' C13' -0.8(3) . . . . ?
C10' C11' C12' C13' -0.9(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C11' C12' C13' C14' 1.4(4) . . . . ?
C12 C13 C14 C9 0.3(4) . . . . ?
C12' C13' C14' C9' -0.5(4) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
C14' C9' C10' C11' 1.2(3) . . . . ?
C15 N2 C6 C1 -2.2(3) . . . . ?
C15 N2 C6 C5 176.9(2) . . . . ?
C15 N2 C7 O1 -0.8(3) . . . . ?
C15 N2 C7 C8 179.89(19) . . . . ?
C15' N2' C6' C1' -2.3(3) . . . . ?
C15' N2' C6' C5' 178.6(2) . . . . ?
C15' N2' C7' O1' 2.0(3) . . . . ?
C15' N2' C7' C8' -178.77(19) . . . . ?

_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 1.431
_oxdiff_exptl_absorpt_empirical_full_min 0.893
