# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_18050301
_database_code_depnum_ccdc_archive 'CCDC 2091450'
loop_
_audit_author_name
_audit_author_address
'Tingting Liu'
;South China Normal University
China
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;
_audit_creation_date             2018-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H22 N2 O'
_chemical_formula_sum            'C29 H22 N2 O'
_chemical_formula_weight         414.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     TPAPLCHO
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7989(4)
_cell_length_b                   9.2736(4)
_cell_length_c                   15.9266(8)
_cell_angle_alpha                101.526(4)
_cell_angle_beta                 90.300(4)
_cell_angle_gamma                109.404(4)
_cell_volume                     1061.34(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4106
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.4480
_cell_measurement_theta_min      5.1530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6113
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.640
_diffrn_reflns_theta_min         5.176
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  74.00   1.00    1.90    --   40.84 -77.00 -90.00   98
  2  ω     49.00 138.00   1.00    7.60    --  108.22 -61.00-180.00   89
  3  ω     83.00 122.00   1.00    7.60    --  108.22-125.00-120.00   39
  4  ω     37.00 119.00   1.00    7.60    --  108.22-125.00  30.00   82
  5  ω     36.00  75.00   1.00    7.60    --  108.22-125.00-120.00   39
  6  ω     78.00 172.00   1.00    7.60    --  108.22  30.00 -90.00   94
  7  ω     99.00 143.00   1.00    7.60    --  108.22 125.00-180.00   44
  8  ω    106.00 176.00   1.00    7.60    --  108.22 125.00-150.00   70
  9  ω    101.00 177.00   1.00    7.60    --  108.22 125.00 -90.00   76
 10  ω     80.00 174.00   1.00    7.60    --  108.22  30.00   0.00   94
 11  ω    115.00 157.00   1.00    7.60    --  108.22 125.00 150.00   42
 12  ω   -113.00 -12.00   1.00    1.90    --  -40.84 -57.00  30.00  101
 13  ω   -112.00 -16.00   1.00    1.90    --  -40.84 -57.00 150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0993793000
_diffrn_orient_matrix_UB_12      0.0334030000
_diffrn_orient_matrix_UB_13      -0.0737912000
_diffrn_orient_matrix_UB_21      -0.0056075000
_diffrn_orient_matrix_UB_22      0.1513074000
_diffrn_orient_matrix_UB_23      0.0592499000
_diffrn_orient_matrix_UB_31      0.1849829000
_diffrn_orient_matrix_UB_32      0.0921718000
_diffrn_orient_matrix_UB_33      -0.0291332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                3687
_reflns_number_total             4066
_reflns_odcompleteness_completeness 98.47
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    ?
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4066
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.032
_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)+(0.0662P)²+0.2401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1164
_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:
 C25(H25), C24(H24), C2(H2), C22(H22), C5(H5), C3(H3), C6(H6), C9(H9),
 C19(H19), C21(H21), C11(H11), C10(H10), C13(H13), C15(H15), C12(H12), C31(H31),
  C27(H27), C18(H18), C29(H29), C17(H17), C28(H28), C16(H16)
;
_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
O32 O 0.24669(14) 0.23426(13) 0.35800(7) 0.0383(3) Uani 1 1 d . . . . .
N26 N -0.04185(15) 0.24831(12) 0.48385(7) 0.0244(2) Uani 1 1 d . . . . .
N7 N 1.01936(15) 0.27864(13) 0.84430(8) 0.0277(3) Uani 1 1 d . . . . .
C23 C 0.10618(17) 0.25598(15) 0.54014(8) 0.0230(3) Uani 1 1 d . . . . .
C4 C 0.55398(17) 0.27225(15) 0.70218(8) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.86433(17) 0.27459(15) 0.79741(8) 0.0240(3) Uani 1 1 d . . . . .
C20 C 0.39680(17) 0.26959(14) 0.64844(8) 0.0230(3) Uani 1 1 d . . . . .
C25 C 0.41327(18) 0.38672(15) 0.60251(8) 0.0246(3) Uani 1 1 d . . . . .
H25 H 0.5221 0.4705 0.6084 0.030 Uiso 1 1 calc R . . . .
C30 C -0.03812(19) 0.26117(14) 0.39845(8) 0.0261(3) Uani 1 1 d . . . . .
C8 C 1.04552(17) 0.14212(15) 0.86119(8) 0.0242(3) Uani 1 1 d . . . . .
C24 C 0.26999(18) 0.37961(15) 0.54838(8) 0.0248(3) Uani 1 1 d . . . . .
H24 H 0.2834 0.4575 0.5176 0.030 Uiso 1 1 calc R . . . .
C2 C 0.82538(18) 0.41252(15) 0.79908(8) 0.0256(3) Uani 1 1 d . . . . .
H2 H 0.9019 0.5065 0.8325 0.031 Uiso 1 1 calc R . . . .
C22 C 0.08379(17) 0.14157(14) 0.58759(8) 0.0238(3) Uani 1 1 d . . . . .
H22 H -0.0275 0.0611 0.5838 0.029 Uiso 1 1 calc R . . . .
C5 C 0.59224(18) 0.13487(15) 0.70162(8) 0.0253(3) Uani 1 1 d . . . . .
H5 H 0.5127 0.0404 0.6700 0.030 Uiso 1 1 calc R . . . .
C3 C 0.67496(17) 0.41093(15) 0.75177(8) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.6541 0.5044 0.7531 0.029 Uiso 1 1 calc R . . . .
C6 C 0.74466(18) 0.13531(15) 0.74659(8) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.7680 0.0424 0.7431 0.031 Uiso 1 1 calc R . . . .
C9 C 1.21845(18) 0.12891(16) 0.85604(8) 0.0269(3) Uani 1 1 d . . . . .
H9 H 1.3143 0.2087 0.8413 0.032 Uiso 1 1 calc R . . . .
C19 C 1.25747(18) 0.51006(16) 0.81507(9) 0.0285(3) Uani 1 1 d . . . . .
H19 H 1.2252 0.4734 0.7564 0.034 Uiso 1 1 calc R . . . .
C21 C 0.22901(18) 0.14832(14) 0.64071(8) 0.0241(3) Uani 1 1 d . . . . .
H21 H 0.2145 0.0707 0.6718 0.029 Uiso 1 1 calc R . . . .
C14 C 1.16449(17) 0.42477(15) 0.87320(9) 0.0258(3) Uani 1 1 d . . . . .
C11 C 1.10625(19) -0.12311(16) 0.89405(9) 0.0297(3) Uani 1 1 d . . . . .
H11 H 1.1260 -0.2117 0.9045 0.036 Uiso 1 1 calc R . . . .
C10 C 1.24844(18) -0.00253(17) 0.87275(9) 0.0293(3) Uani 1 1 d . . . . .
H10 H 1.3644 -0.0098 0.8696 0.035 Uiso 1 1 calc R . . . .
C13 C 0.90397(18) 0.02171(16) 0.88413(9) 0.0281(3) Uani 1 1 d . . . . .
H13 H 0.7886 0.0298 0.8891 0.034 Uiso 1 1 calc R . . . .
C15 C 1.21290(19) 0.48033(17) 0.96083(9) 0.0312(3) Uani 1 1 d . . . . .
H15 H 1.1505 0.4232 0.9998 0.037 Uiso 1 1 calc R . . . .
C12 C 0.93479(19) -0.11004(17) 0.89957(9) 0.0307(3) Uani 1 1 d . . . . .
H12 H 0.8391 -0.1905 0.9138 0.037 Uiso 1 1 calc R . . . .
C31 C 0.1039(2) 0.25378(16) 0.34219(9) 0.0314(3) Uani 1 1 d . . . . .
H31 H 0.0842 0.2654 0.2867 0.038 Uiso 1 1 calc R . . . .
C27 C -0.21250(19) 0.23450(16) 0.50867(10) 0.0307(3) Uani 1 1 d . . . . .
H27 H -0.2504 0.2245 0.5631 0.037 Uiso 1 1 calc R . . . .
C18 C 1.39914(19) 0.65065(17) 0.84497(10) 0.0323(3) Uani 1 1 d . . . . .
H18 H 1.4620 0.7077 0.8061 0.039 Uiso 1 1 calc R . . . .
C29 C -0.2109(2) 0.25489(15) 0.37199(10) 0.0318(3) Uani 1 1 d . . . . .
H29 H -0.2475 0.2612 0.3176 0.038 Uiso 1 1 calc R . . . .
C17 C 1.44725(18) 0.70628(17) 0.93252(11) 0.0339(3) Uani 1 1 d . . . . .
H17 H 1.5417 0.8005 0.9522 0.041 Uiso 1 1 calc R . . . .
C28 C -0.32014(19) 0.23757(16) 0.44086(10) 0.0331(3) Uani 1 1 d . . . . .
H28 H -0.4422 0.2296 0.4409 0.040 Uiso 1 1 calc R . . . .
C16 C 1.3543(2) 0.62105(18) 0.99035(10) 0.0356(3) Uani 1 1 d . . . . .
H16 H 1.3865 0.6579 1.0490 0.043 Uiso 1 1 calc R . . . .


_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
O32 C31 1.2190(19) . ?
N26 C23 1.4319(16) . ?
N26 C30 1.3885(17) . ?
N26 C27 1.3625(18) . ?
N7 C1 1.4036(16) . ?
N7 C8 1.4227(17) . ?
N7 C14 1.4337(17) . ?
C23 C24 1.3888(19) . ?
C23 C22 1.3878(18) . ?
C4 C20 1.4820(17) . ?
C4 C5 1.4001(18) . ?
C4 C3 1.3957(19) . ?
C1 C2 1.4049(18) . ?
C1 C6 1.4028(19) . ?
C20 C25 1.3991(18) . ?
C20 C21 1.3991(18) . ?
C25 H25 0.9300 . ?
C25 C24 1.3837(18) . ?
C30 C31 1.439(2) . ?
C30 C29 1.3889(19) . ?
C8 C9 1.3955(18) . ?
C8 C13 1.3955(19) . ?
C24 H24 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.3852(18) . ?
C22 H22 0.9300 . ?
C22 C21 1.3871(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.3830(18) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.3891(19) . ?
C19 H19 0.9300 . ?
C19 C14 1.388(2) . ?
C19 C18 1.392(2) . ?
C21 H21 0.9300 . ?
C14 C15 1.391(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.388(2) . ?
C11 C12 1.384(2) . ?
C10 H10 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.3876(19) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(2) . ?
C12 H12 0.9300 . ?
C31 H31 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.375(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.389(2) . ?
C29 H29 0.9300 . ?
C29 C28 1.394(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.384(2) . ?
C28 H28 0.9300 . ?
C16 H16 0.9300 . ?

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
C30 N26 C23 127.76(11) . . ?
C27 N26 C23 123.95(11) . . ?
C27 N26 C30 108.22(11) . . ?
C1 N7 C8 123.10(11) . . ?
C1 N7 C14 119.52(11) . . ?
C8 N7 C14 117.29(11) . . ?
C24 C23 N26 119.86(11) . . ?
C22 C23 N26 119.78(11) . . ?
C22 C23 C24 120.34(12) . . ?
C5 C4 C20 120.71(11) . . ?
C3 C4 C20 122.12(11) . . ?
C3 C4 C5 117.09(12) . . ?
N7 C1 C2 120.45(12) . . ?
C6 C1 N7 121.99(11) . . ?
C6 C1 C2 117.55(12) . . ?
C25 C20 C4 120.85(11) . . ?
C21 C20 C4 121.04(11) . . ?
C21 C20 C25 118.10(12) . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 120.94(12) . . ?
C24 C25 H25 119.5 . . ?
N26 C30 C31 127.29(12) . . ?
N26 C30 C29 107.06(12) . . ?
C29 C30 C31 124.78(13) . . ?
C9 C8 N7 119.18(12) . . ?
C13 C8 N7 121.99(12) . . ?
C13 C8 C9 118.83(12) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.87(11) . . ?
C25 C24 H24 120.1 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.13(12) . . ?
C3 C2 H2 119.4 . . ?
C23 C22 H22 120.3 . . ?
C21 C22 C23 119.38(12) . . ?
C21 C22 H22 120.3 . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.03(12) . . ?
C6 C5 H5 119.0 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.51(12) . . ?
C2 C3 H3 119.2 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.65(12) . . ?
C5 C6 H6 119.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.49(12) . . ?
C10 C9 H9 119.8 . . ?
C14 C19 H19 120.2 . . ?
C14 C19 C18 119.68(14) . . ?
C18 C19 H19 120.2 . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.30(11) . . ?
C22 C21 H21 119.4 . . ?
C19 C14 N7 120.97(13) . . ?
C19 C14 C15 119.92(13) . . ?
C15 C14 N7 119.11(12) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C12 C11 C10 119.27(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.37(12) . . ?
C11 C10 H10 119.8 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.23(12) . . ?
C12 C13 H13 119.9 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.15(14) . . ?
C16 C15 H15 119.9 . . ?
C11 C12 C13 120.80(13) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
O32 C31 C30 128.29(13) . . ?
O32 C31 H31 115.9 . . ?
C30 C31 H31 115.9 . . ?
N26 C27 H27 125.2 . . ?
N26 C27 C28 109.59(13) . . ?
C28 C27 H27 125.2 . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.39(13) . . ?
C17 C18 H18 119.8 . . ?
C30 C29 H29 125.8 . . ?
C30 C29 C28 108.42(13) . . ?
C28 C29 H29 125.8 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.82(13) . . ?
C16 C17 H17 120.1 . . ?
C27 C28 C29 106.72(12) . . ?
C27 C28 H28 126.6 . . ?
C29 C28 H28 126.6 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.04(14) . . ?
C17 C16 H16 120.0 . . ?

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
N26 C23 C24 C25 -179.75(11) . . . . ?
N26 C23 C22 C21 178.79(11) . . . . ?
N26 C30 C31 O32 0.4(2) . . . . ?
N26 C30 C29 C28 -0.25(15) . . . . ?
N26 C27 C28 C29 -0.36(16) . . . . ?
N7 C1 C2 C3 178.68(12) . . . . ?
N7 C1 C6 C5 179.52(12) . . . . ?
N7 C8 C9 C10 179.57(12) . . . . ?
N7 C8 C13 C12 179.60(12) . . . . ?
N7 C14 C15 C16 179.41(12) . . . . ?
C23 N26 C30 C31 13.5(2) . . . . ?
C23 N26 C30 C29 -176.86(11) . . . . ?
C23 N26 C27 C28 177.24(11) . . . . ?
C23 C22 C21 C20 1.02(19) . . . . ?
C4 C20 C25 C24 176.19(11) . . . . ?
C4 C20 C21 C22 -177.17(11) . . . . ?
C4 C5 C6 C1 2.3(2) . . . . ?
C1 N7 C8 C9 139.53(13) . . . . ?
C1 N7 C8 C13 -41.51(19) . . . . ?
C1 N7 C14 C19 -60.59(17) . . . . ?
C1 N7 C14 C15 119.95(14) . . . . ?
C1 C2 C3 C4 1.5(2) . . . . ?
C20 C4 C5 C6 175.62(12) . . . . ?
C20 C4 C3 C2 -177.43(11) . . . . ?
C20 C25 C24 C23 0.94(19) . . . . ?
C25 C20 C21 C22 1.49(19) . . . . ?
C30 N26 C23 C24 50.60(18) . . . . ?
C30 N26 C23 C22 -130.80(13) . . . . ?
C30 N26 C27 C28 0.21(15) . . . . ?
C30 C29 C28 C27 0.38(16) . . . . ?
C8 N7 C1 C2 165.45(12) . . . . ?
C8 N7 C1 C6 -15.48(19) . . . . ?
C8 N7 C14 C19 116.09(14) . . . . ?
C8 N7 C14 C15 -63.37(17) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C8 C13 C12 C11 1.2(2) . . . . ?
C24 C23 C22 C21 -2.62(18) . . . . ?
C2 C1 C6 C5 -1.39(19) . . . . ?
C22 C23 C24 C25 1.66(19) . . . . ?
C5 C4 C20 C25 -137.28(13) . . . . ?
C5 C4 C20 C21 41.34(17) . . . . ?
C5 C4 C3 C2 -0.63(19) . . . . ?
C3 C4 C20 C25 39.40(18) . . . . ?
C3 C4 C20 C21 -141.97(13) . . . . ?
C3 C4 C5 C6 -1.22(19) . . . . ?
C6 C1 C2 C3 -0.43(19) . . . . ?
C9 C8 C13 C12 -1.4(2) . . . . ?
C19 C14 C15 C16 -0.1(2) . . . . ?
C19 C18 C17 C16 0.3(2) . . . . ?
C21 C20 C25 C24 -2.48(19) . . . . ?
C14 N7 C1 C2 -18.07(18) . . . . ?
C14 N7 C1 C6 160.99(12) . . . . ?
C14 N7 C8 C9 -37.02(18) . . . . ?
C14 N7 C8 C13 141.94(13) . . . . ?
C14 C19 C18 C17 -0.3(2) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C13 C8 C9 C10 0.6(2) . . . . ?
C12 C11 C10 C9 -0.8(2) . . . . ?
C31 C30 C29 C28 169.71(13) . . . . ?
C27 N26 C23 C24 -125.83(14) . . . . ?
C27 N26 C23 C22 52.77(17) . . . . ?
C27 N26 C30 C31 -169.60(13) . . . . ?
C27 N26 C30 C29 0.03(14) . . . . ?
C18 C19 C14 N7 -179.27(12) . . . . ?
C18 C19 C14 C15 0.2(2) . . . . ?
C18 C17 C16 C15 -0.2(2) . . . . ?
C29 C30 C31 O32 -167.51(14) . . . . ?

_olex2_date_sample_data_collection 2018-05-03
_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 1.337
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# 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_mo_d8v17613_0m
_database_code_depnum_ccdc_archive 'CCDC 2091452'
loop_
_audit_author_name
_audit_author_address
'Tingting Liu'
;South China Normal University
China
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 N4'
_chemical_formula_weight         462.53

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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. 
;

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'
'-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                   16.9114(12)
_cell_length_b                   8.4024(6)
_cell_length_c                   35.811(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5088.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8908
_cell_measurement_theta_min      5.328
_cell_measurement_theta_max      49.699

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5619
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76672
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.1382
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.574
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             4465
_reflns_number_gt                2797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+1.4260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4465
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1627
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.50948(10) 0.2505(2) 0.52172(5) 0.0553(5) Uani 1 1 d . . . . .
N2 N 0.51185(12) 0.3017(3) 0.79857(5) 0.0674(6) Uani 1 1 d . . . . .
N3 N 0.25764(16) 0.3510(5) 0.44400(8) 0.1374(14) Uani 1 1 d . . . . .
N4 N 0.23752(17) 0.6516(4) 0.54199(8) 0.1136(11) Uani 1 1 d . . . . .
C1 C 0.32303(14) 0.4654(3) 0.50198(7) 0.0623(7) Uani 1 1 d . . . . .
C2 C 0.39392(14) 0.4201(3) 0.51519(6) 0.0568(6) Uani 1 1 d . . . . .
H2 H 0.4083 0.4646 0.5380 0.068 Uiso 1 1 calc R U . . .
C3 C 0.44978(13) 0.3144(3) 0.49940(6) 0.0534(6) Uani 1 1 d . . . . .
C4 C 0.46539(16) 0.2676(3) 0.46316(7) 0.0651(7) Uani 1 1 d . . . . .
H4 H 0.4352 0.2924 0.4423 0.078 Uiso 1 1 calc R U . . .
C5 C 0.53391(17) 0.1771(3) 0.46335(7) 0.0731(8) Uani 1 1 d . . . . .
H5 H 0.5581 0.1315 0.4426 0.088 Uiso 1 1 calc R U . . .
C6 C 0.55967(15) 0.1671(3) 0.49946(7) 0.0670(7) Uani 1 1 d . . . . .
H6 H 0.6043 0.1121 0.5075 0.080 Uiso 1 1 calc R U . . .
C7 C 0.51175(12) 0.2587(3) 0.56150(6) 0.0514(6) Uani 1 1 d . . . . .
C8 C 0.44467(13) 0.2210(3) 0.58201(6) 0.0568(6) Uani 1 1 d . . . . .
H8 H 0.3989 0.1881 0.5699 0.068 Uiso 1 1 calc R U . . .
C9 C 0.44591(13) 0.2324(3) 0.62029(6) 0.0569(6) Uani 1 1 d . . . . .
H9 H 0.4005 0.2078 0.6337 0.068 Uiso 1 1 calc R U . . .
C10 C 0.51371(13) 0.2800(3) 0.63949(6) 0.0532(6) Uani 1 1 d . . . . .
C11 C 0.57998(13) 0.3155(3) 0.61809(7) 0.0608(6) Uani 1 1 d . . . . .
H11 H 0.6262 0.3472 0.6301 0.073 Uiso 1 1 calc R U . . .
C12 C 0.57946(13) 0.3053(3) 0.57978(6) 0.0597(6) Uani 1 1 d . . . . .
H12 H 0.6248 0.3299 0.5662 0.072 Uiso 1 1 calc R U . . .
C13 C 0.51389(13) 0.2889(3) 0.68048(7) 0.0550(6) Uani 1 1 d . . . . .
C14 C 0.44887(14) 0.3433(3) 0.70043(6) 0.0593(6) Uani 1 1 d . . . . .
H14 H 0.4042 0.3763 0.6874 0.071 Uiso 1 1 calc R U . . .
C15 C 0.44848(15) 0.3502(3) 0.73864(6) 0.0623(7) Uani 1 1 d . . . . .
H15 H 0.4041 0.3890 0.7510 0.075 Uiso 1 1 calc R U . . .
C16 C 0.51359(14) 0.2997(3) 0.75913(6) 0.0583(6) Uani 1 1 d . . . . .
C17 C 0.57929(15) 0.2457(3) 0.73966(6) 0.0612(6) Uani 1 1 d . . . . .
H17 H 0.6238 0.2122 0.7527 0.073 Uiso 1 1 calc R U . . .
C18 C 0.57932(15) 0.2410(3) 0.70132(6) 0.0599(6) Uani 1 1 d . . . . .
H18 H 0.6242 0.2050 0.6889 0.072 Uiso 1 1 calc R U . . .
C19 C 0.43943(15) 0.2707(3) 0.81741(7) 0.0627(7) Uani 1 1 d . . . . .
C20 C 0.38954(16) 0.1516(3) 0.80519(7) 0.0713(7) Uani 1 1 d . . . . .
H20 H 0.4035 0.0907 0.7845 0.086 Uiso 1 1 calc R U . . .
C21 C 0.31890(18) 0.1219(4) 0.82344(9) 0.0860(9) Uani 1 1 d . . . . .
H21 H 0.2852 0.0428 0.8147 0.103 Uiso 1 1 calc R U . . .
C22 C 0.29862(19) 0.2081(5) 0.85412(10) 0.0926(10) Uani 1 1 d . . . . .
H22 H 0.2516 0.1866 0.8666 0.111 Uiso 1 1 calc R U . . .
C23 C 0.3474(2) 0.3261(4) 0.86663(8) 0.0897(9) Uani 1 1 d . . . . .
H23 H 0.3331 0.3850 0.8876 0.108 Uiso 1 1 calc R U . . .
C24 C 0.41799(18) 0.3592(3) 0.84846(7) 0.0773(8) Uani 1 1 d . . . . .
H24 H 0.4507 0.4403 0.8571 0.093 Uiso 1 1 calc R U . . .
C25 C 0.58146(17) 0.3287(3) 0.81950(7) 0.0685(7) Uani 1 1 d . . . . .
C26 C 0.5956(2) 0.2435(4) 0.85170(8) 0.0888(9) Uani 1 1 d . . . . .
H26 H 0.5601 0.1654 0.8594 0.107 Uiso 1 1 calc R U . . .
C27 C 0.6627(3) 0.2747(6) 0.87256(10) 0.1140(13) Uani 1 1 d . . . . .
H27 H 0.6714 0.2191 0.8946 0.137 Uiso 1 1 calc R U . . .
C28 C 0.7164(2) 0.3864(6) 0.86108(13) 0.1233(16) Uani 1 1 d . . . . .
H28 H 0.7616 0.4057 0.8752 0.148 Uiso 1 1 calc R U . . .
C29 C 0.70342(19) 0.4697(5) 0.82884(11) 0.1026(11) Uani 1 1 d . . . . .
H29 H 0.7402 0.5445 0.8208 0.123 Uiso 1 1 calc R U . . .
C30 C 0.63592(17) 0.4427(4) 0.80825(8) 0.0804(8) Uani 1 1 d . . . . .
H30 H 0.6268 0.5014 0.7867 0.097 Uiso 1 1 calc R U . . .
C31 C 0.28813(16) 0.4028(4) 0.46911(8) 0.0869(9) Uani 1 1 d . . . . .
C32 C 0.27518(17) 0.5700(4) 0.52377(8) 0.0772(8) 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
N1 C6 1.359(3) . ?
N1 C3 1.395(3) . ?
N1 C7 1.427(3) . ?
N2 C16 1.413(3) . ?
N2 C25 1.414(3) . ?
N2 C19 1.422(3) . ?
N3 C31 1.124(3) . ?
N4 C32 1.141(4) . ?
C1 C2 1.344(3) . ?
C1 C31 1.418(4) . ?
C1 C32 1.427(4) . ?
C2 C3 1.414(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.376(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.374(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(3) . ?
C10 C13 1.470(3) . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 C18 1.394(3) . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(3) . ?
C17 C18 1.373(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.380(3) . ?
C19 C24 1.386(3) . ?
C20 C21 1.384(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.360(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.388(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.378(4) . ?
C25 C30 1.389(4) . ?
C26 C27 1.384(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.368(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.377(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

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
C6 N1 C3 108.3(2) . . ?
C6 N1 C7 126.4(2) . . ?
C3 N1 C7 124.96(18) . . ?
C16 N2 C25 121.0(2) . . ?
C16 N2 C19 119.4(2) . . ?
C25 N2 C19 119.6(2) . . ?
C2 C1 C31 123.9(3) . . ?
C2 C1 C32 119.2(2) . . ?
C31 C1 C32 116.5(2) . . ?
C1 C2 C3 129.3(2) . . ?
C1 C2 H2 115.4 . . ?
C3 C2 H2 115.4 . . ?
C4 C3 N1 106.9(2) . . ?
C4 C3 C2 133.0(2) . . ?
N1 C3 C2 119.7(2) . . ?
C3 C4 C5 108.1(2) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
C6 C5 C4 107.8(2) . . ?
C6 C5 H5 126.1 . . ?
C4 C5 H5 126.1 . . ?
N1 C6 C5 108.9(2) . . ?
N1 C6 H6 125.5 . . ?
C5 C6 H6 125.5 . . ?
C12 C7 C8 119.5(2) . . ?
C12 C7 N1 120.74(19) . . ?
C8 C7 N1 119.71(19) . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.6(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 116.9(2) . . ?
C11 C10 C13 122.6(2) . . ?
C9 C10 C13 120.6(2) . . ?
C12 C11 C10 122.1(2) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C7 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C14 C13 C18 116.6(2) . . ?
C14 C13 C10 121.9(2) . . ?
C18 C13 C10 121.5(2) . . ?
C15 C14 C13 122.1(2) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.0(2) . . ?
C17 C16 N2 121.5(2) . . ?
C15 C16 N2 120.5(2) . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 121.8(2) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
C20 C19 C24 118.9(3) . . ?
C20 C19 N2 120.6(2) . . ?
C24 C19 N2 120.5(3) . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C19 C24 C23 119.6(3) . . ?
C19 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C26 C25 C30 119.1(3) . . ?
C26 C25 N2 120.3(3) . . ?
C30 C25 N2 120.6(2) . . ?
C25 C26 C27 119.7(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C28 C27 C26 120.8(4) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C29 C28 C27 119.8(4) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.1(4) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C25 120.5(3) . . ?
C29 C30 H30 119.7 . . ?
C25 C30 H30 119.7 . . ?
N3 C31 C1 176.9(3) . . ?
N4 C32 C1 178.3(3) . . ?

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
C31 C1 C2 C3 4.6(4) . . . . ?
C32 C1 C2 C3 177.6(2) . . . . ?
C6 N1 C3 C4 -0.1(3) . . . . ?
C7 N1 C3 C4 -174.1(2) . . . . ?
C6 N1 C3 C2 -173.7(2) . . . . ?
C7 N1 C3 C2 12.3(3) . . . . ?
C1 C2 C3 C4 25.5(4) . . . . ?
C1 C2 C3 N1 -162.9(2) . . . . ?
N1 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C5 172.1(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 N1 C6 C5 0.5(3) . . . . ?
C7 N1 C6 C5 174.4(2) . . . . ?
C4 C5 C6 N1 -0.7(3) . . . . ?
C6 N1 C7 C12 55.0(3) . . . . ?
C3 N1 C7 C12 -132.1(2) . . . . ?
C6 N1 C7 C8 -125.8(2) . . . . ?
C3 N1 C7 C8 47.1(3) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
N1 C7 C8 C9 -178.4(2) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C8 C9 C10 C13 -179.1(2) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C13 C10 C11 C12 179.3(2) . . . . ?
C10 C11 C12 C7 0.0(4) . . . . ?
C8 C7 C12 C11 -0.5(3) . . . . ?
N1 C7 C12 C11 178.7(2) . . . . ?
C11 C10 C13 C14 142.4(2) . . . . ?
C9 C10 C13 C14 -38.6(3) . . . . ?
C11 C10 C13 C18 -38.4(3) . . . . ?
C9 C10 C13 C18 140.7(2) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C10 C13 C14 C15 179.3(2) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C17 1.4(4) . . . . ?
C14 C15 C16 N2 -177.7(2) . . . . ?
C25 N2 C16 C17 32.5(3) . . . . ?
C19 N2 C16 C17 -145.4(2) . . . . ?
C25 N2 C16 C15 -148.4(2) . . . . ?
C19 N2 C16 C15 33.7(3) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
N2 C16 C17 C18 178.5(2) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
C10 C13 C18 C17 -178.5(2) . . . . ?
C16 N2 C19 C20 41.5(3) . . . . ?
C25 N2 C19 C20 -136.4(2) . . . . ?
C16 N2 C19 C24 -138.8(2) . . . . ?
C25 N2 C19 C24 43.3(3) . . . . ?
C24 C19 C20 C21 0.6(4) . . . . ?
N2 C19 C20 C21 -179.7(2) . . . . ?
C19 C20 C21 C22 -1.3(4) . . . . ?
C20 C21 C22 C23 1.1(5) . . . . ?
C21 C22 C23 C24 -0.3(5) . . . . ?
C20 C19 C24 C23 0.3(4) . . . . ?
N2 C19 C24 C23 -179.4(2) . . . . ?
C22 C23 C24 C19 -0.4(4) . . . . ?
C16 N2 C25 C26 -140.0(3) . . . . ?
C19 N2 C25 C26 37.9(3) . . . . ?
C16 N2 C25 C30 40.9(3) . . . . ?
C19 N2 C25 C30 -141.2(2) . . . . ?
C30 C25 C26 C27 1.1(4) . . . . ?
N2 C25 C26 C27 -178.0(3) . . . . ?
C25 C26 C27 C28 -1.7(5) . . . . ?
C26 C27 C28 C29 0.7(6) . . . . ?
C27 C28 C29 C30 0.9(5) . . . . ?
C28 C29 C30 C25 -1.5(5) . . . . ?
C26 C25 C30 C29 0.4(4) . . . . ?
N2 C25 C30 C29 179.5(2) . . . . ?

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
C8 H8 N4 0.93 2.53 3.448(4) 168.1 8_655

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

