# Electronic Supplementary Material (ESI) for Materials Advances.
# 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_mo_ccAV_20Jun2018_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2151982'
loop_
_audit_author_name
_audit_author_address
'Alex Veinot'
;Queens University
Canada
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-06-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_mo_ccAV_20Jun2018_0m_a 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0043 Ang.
RESPONSE: Crystal was grown by sublimation, so the data are not perfect. We are confident that the model of electron density represents the structure given.
;
_vrf_PLAT911_mo_ccAV_20Jun2018_0m_a 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: Crystal was grown by sublimation, so the data are not perfect. We are confident that the model of electron density represents the structure given.
;
# Added during the CSD deposition process: Monday 14 February 2022 03:18 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 N2'
_chemical_formula_weight         202.29

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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   8.7704(8)
_cell_length_b                   16.1245(16)
_cell_length_c                   8.6071(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.294(3)
_cell_angle_gamma                90
_cell_volume                     1216.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6233
_cell_measurement_theta_min      2.526
_cell_measurement_theta_max      25.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.107
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS v2016/2 (Apex3, Bruker AXS)'
_exptl_absorpt_special_details   
;The ratio of minimum to maximum transmission is 0.955.
;
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;high brilliance Incoatec I\ms microfocus tube
;
_diffrn_radiation_monochromator  'HELIOS multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker AXS D8 Venture Duo'
_diffrn_detector                 
;Bruker AXS PHOTON II Charge-Integrating Pixel Array Detector (CPAD)
;
_diffrn_measurement_method       'shutterless rotation images,φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18978
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.464
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2491
_reflns_number_gt                2203
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.991
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997

_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       
;APEX3 software package v2018.7-2(Bruker AXS).
;
_computing_cell_refinement       
;Saint V8.38A and SADABS V2016/2 (Apex3 v2018.7-2; Bruker AXS).
 Ref. for SADABS: Krause, L.; Herbst-Irmer, R.; Sheldrick G.M.; 
 Stalke D., J. Appl. Cryst., 48 (2015), 3-10.
;
_computing_data_reduction        
;Saint V8.38A and SADABS V2016/2 (Apex3 v2018.7-2; Bruker AXS).
 Ref. for SADABS: Krause, L.; Herbst-Irmer, R.; Sheldrick G.M.; 
 Stalke D., J. Appl. Cryst., 48 (2015), 3-10. 
;
_computing_structure_solution    
; SHELXT-2014/5 (Sheldrick, 2014). G. M. Sheldrick, Acta Cryst. 2015, A71,
  3-8.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0484P)²+0.3325P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2491
_refine_ls_number_parameters     140
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_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 0.5999(2) 0.59304(12) 0.5385(2) 0.0392(5) Uani 1 1 d . . . . .
N2 N 0.5964(3) 0.68192(14) 0.3527(3) 0.0470(6) Uani 1 1 d . . . . .
C1 C 0.6897(3) 0.65067(19) 0.4689(4) 0.0499(7) Uani 1 1 d . . . . .
C2 C 0.4536(3) 0.59003(14) 0.4705(3) 0.0353(5) Uani 1 1 d . . . . .
C3 C 0.3253(3) 0.54360(16) 0.5026(3) 0.0425(6) Uani 1 1 d . . . . .
H3 H 0.3272 0.5030 0.5826 0.051 Uiso 1 1 calc R U . . .
C4 C 0.1940(3) 0.5593(2) 0.4119(4) 0.0538(8) Uani 1 1 d . . . . .
H4 H 0.1036 0.5293 0.4316 0.065 Uiso 1 1 calc R U . . .
C5 C 0.1910(3) 0.6174(2) 0.2941(4) 0.0573(8) Uani 1 1 d . . . . .
H5 H 0.0987 0.6261 0.2348 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3181(3) 0.66317(17) 0.2598(3) 0.0484(7) Uani 1 1 d . . . . .
H6 H 0.3156 0.7030 0.1785 0.058 Uiso 1 1 calc R U . . .
C7 C 0.4510(3) 0.64799(15) 0.3507(3) 0.0377(6) Uani 1 1 d . . . . .
C8 C 0.6450(3) 0.54931(17) 0.6827(3) 0.0445(7) Uani 1 1 d . . . . .
H8 H 0.5819 0.4978 0.6881 0.053 Uiso 1 1 calc R U . . .
C9 C 0.6096(4) 0.6030(2) 0.8214(4) 0.0593(8) Uani 1 1 d . . . . .
H9A H 0.6678 0.6548 0.8172 0.089 Uiso 1 1 calc R U . . .
H9B H 0.6378 0.5733 0.9177 0.089 Uiso 1 1 calc R U . . .
H9C H 0.5002 0.6157 0.8190 0.089 Uiso 1 1 calc R U . . .
C10 C 0.8112(4) 0.5235(2) 0.6827(4) 0.0588(8) Uani 1 1 d . . . . .
H10A H 0.8300 0.4927 0.5872 0.088 Uiso 1 1 calc R U . . .
H10B H 0.8349 0.4882 0.7731 0.088 Uiso 1 1 calc R U . . .
H10C H 0.8761 0.5730 0.6878 0.088 Uiso 1 1 calc R U . . .
C11 C 0.6416(4) 0.74902(19) 0.2470(4) 0.0563(8) Uani 1 1 d . . . . .
H11 H 0.5637 0.7518 0.1591 0.068 Uiso 1 1 calc R U . . .
C12 C 0.7927(5) 0.7299(2) 0.1800(5) 0.0785(12) Uani 1 1 d . . . . .
H12A H 0.7869 0.6764 0.1262 0.118 Uiso 1 1 calc R U . . .
H12B H 0.8714 0.7274 0.2639 0.118 Uiso 1 1 calc R U . . .
H12C H 0.8186 0.7735 0.1062 0.118 Uiso 1 1 calc R U . . .
C13 C 0.6400(4) 0.83133(18) 0.3315(4) 0.0610(9) Uani 1 1 d . . . . .
H13A H 0.6617 0.8761 0.2587 0.092 Uiso 1 1 calc R U . . .
H13B H 0.7180 0.8310 0.4163 0.092 Uiso 1 1 calc R U . . .
H13C H 0.5394 0.8402 0.3743 0.092 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 1.372(3) . ?
N1 C2 1.390(3) . ?
N1 C8 1.468(3) . ?
N2 C1 1.363(4) . ?
N2 C7 1.387(3) . ?
N2 C11 1.478(3) . ?
C2 C3 1.388(4) . ?
C2 C7 1.391(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(4) . ?
C6 H6 0.9500 . ?
C8 C10 1.515(4) . ?
C8 C9 1.517(4) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.498(5) . ?
C11 C13 1.514(5) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 C2 112.1(2) . . ?
C1 N1 C8 123.7(2) . . ?
C2 N1 C8 123.5(2) . . ?
C1 N2 C7 112.8(2) . . ?
C1 N2 C11 123.7(2) . . ?
C7 N2 C11 123.4(2) . . ?
N2 C1 N1 103.5(2) . . ?
C3 C2 N1 132.6(2) . . ?
C3 C2 C7 121.4(2) . . ?
N1 C2 C7 106.0(2) . . ?
C4 C3 C2 116.8(3) . . ?
C4 C3 H3 121.6 . . ?
C2 C3 H3 121.6 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 116.7(3) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
N2 C7 C2 105.6(2) . . ?
N2 C7 C6 133.0(2) . . ?
C2 C7 C6 121.3(2) . . ?
N1 C8 C10 111.0(2) . . ?
N1 C8 C9 109.5(2) . . ?
C10 C8 C9 112.6(3) . . ?
N1 C8 H8 107.8 . . ?
C10 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 110.5(3) . . ?
N2 C11 C13 109.8(3) . . ?
C12 C11 C13 113.0(3) . . ?
N2 C11 H11 107.8 . . ?
C12 C11 H11 107.8 . . ?
C13 C11 H11 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C7 N2 C1 N1 2.0(3) . . . . ?
C11 N2 C1 N1 177.9(3) . . . . ?
C2 N1 C1 N2 -1.6(3) . . . . ?
C8 N1 C1 N2 -172.6(2) . . . . ?
C1 N1 C2 C3 -178.7(3) . . . . ?
C8 N1 C2 C3 -7.7(4) . . . . ?
C1 N1 C2 C7 0.7(3) . . . . ?
C8 N1 C2 C7 171.7(2) . . . . ?
N1 C2 C3 C4 177.7(3) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C1 N2 C7 C2 -1.6(3) . . . . ?
C11 N2 C7 C2 -177.6(3) . . . . ?
C1 N2 C7 C6 176.7(3) . . . . ?
C11 N2 C7 C6 0.7(5) . . . . ?
C3 C2 C7 N2 180.0(2) . . . . ?
N1 C2 C7 N2 0.6(3) . . . . ?
C3 C2 C7 C6 1.4(4) . . . . ?
N1 C2 C7 C6 -178.0(2) . . . . ?
C5 C6 C7 N2 -178.7(3) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C1 N1 C8 C10 -41.5(4) . . . . ?
C2 N1 C8 C10 148.6(3) . . . . ?
C1 N1 C8 C9 83.5(3) . . . . ?
C2 N1 C8 C9 -86.5(3) . . . . ?
C1 N2 C11 C12 49.9(4) . . . . ?
C7 N2 C11 C12 -134.6(3) . . . . ?
C1 N2 C11 C13 -75.3(4) . . . . ?
C7 N2 C11 C13 100.3(3) . . . . ?

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
C12 H12C C2 0.98 2.78 3.725(4) 162.5 4_564
C12 H12C C7 0.98 2.83 3.762(4) 159.8 4_564

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method Sublimation
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Heat-sensitive
####################################################################### 
# 
# 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_ccAV_125_15Jun2018_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2151983'
loop_
_audit_author_name
_audit_author_address
'Alex Veinot'
;Queens University
Canada
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-06-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT911_mo_ccAV_125_15Jun2018_0m_a 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         63 Report
RESPONSE: Crystal was grown by sublimation, so the data are not perfect. We are confident that the model of electron density represents the structure given.
;
_vrf_PLAT913_mo_ccAV_125_15Jun2018_0m_a 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         25 Note
RESPONSE: Crystal was grown by sublimation, so the data are not perfect. We are confident that the model of electron density represents the structure given.
;
# Added during the CSD deposition process: Monday 14 February 2022 03:18 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 N2'
_chemical_formula_weight         202.29

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   10.5854(3)
_cell_length_b                   10.8595(3)
_cell_length_c                   12.3706(4)
_cell_angle_alpha                100.0740(10)
_cell_angle_beta                 114.9300(10)
_cell_angle_gamma                106.0110(10)
_cell_volume                     1168.30(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      35.91

_exptl_crystal_description       block-like
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.416
_exptl_crystal_size_min          0.403
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   '(SADABS, Bruker, 2008)'
_exptl_absorpt_special_details   
;The ratio of minimum to maximum transmission is 0.942.
;
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;high brilliance Incoatec I\ms microfocus tube
;
_diffrn_radiation_monochromator  'HELIOS multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker AXS D8 Venture Duo'
_diffrn_detector                 
;Bruker AXS PHOTON II Charge-Integrating Pixel Array Detector (CPAD)
;
_diffrn_measurement_method       'shutterless rotation images,φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            66668
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         36.334
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             10264
_reflns_number_gt                8462
_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       
;APEX3 software package v2018.7-2(Bruker AXS).
;
_computing_cell_refinement       
;Saint V8.38A and SADABS V2016/2 (Apex3 v2018.7-2; Bruker AXS).
 Ref. for SADABS: Krause, L.; Herbst-Irmer, R.; Sheldrick G.M.; 
 Stalke D., J. Appl. Cryst., 48 (2015), 3-10.
;
_computing_data_reduction        
;Saint V8.38A and SADABS V2016/2 (Apex3 v2018.7-2; Bruker AXS).
 Ref. for SADABS: Krause, L.; Herbst-Irmer, R.; Sheldrick G.M.; 
 Stalke D., J. Appl. Cryst., 48 (2015), 3-10. 
;
_computing_structure_solution    
; SHELXT-2014/5 (Sheldrick, 2014). G. M. Sheldrick, Acta Cryst. 2015, A71,
  3-8.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0656P)²+0.1936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10264
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.63779(8) 0.71752(6) 0.30173(6) 0.02569(12) Uani 1 1 d . . . . .
N2 N 0.77145(7) 0.86223(6) 0.50222(6) 0.02356(11) Uani 1 1 d . . . . .
N3 N 0.10685(7) 0.21382(6) 0.04381(6) 0.02429(11) Uani 1 1 d . . . . .
N4 N 0.17225(7) 0.42825(6) 0.16031(6) 0.02325(11) Uani 1 1 d . . . . .
C1 C 0.73293(8) 0.73742(7) 0.42041(6) 0.02297(12) Uani 1 1 d . . . . .
C2 C 0.79986(9) 0.63770(7) 0.46220(7) 0.02703(14) Uani 1 1 d . . . . .
H2 H 0.8109 0.6407 0.5471 0.032 Uiso 1 1 calc R U . . .
C3 C 0.95718(11) 0.67819(10) 0.47454(10) 0.03794(19) Uani 1 1 d . . . . .
H3A H 0.9481 0.6743 0.3917 0.057 Uiso 1 1 calc R U . . .
H3B H 1.0024 0.6153 0.5055 0.057 Uiso 1 1 calc R U . . .
H3C H 1.0217 0.7708 0.5343 0.057 Uiso 1 1 calc R U . . .
C4 C 0.69721(12) 0.49359(8) 0.37010(8) 0.03640(18) Uani 1 1 d . . . . .
H4A H 0.6867 0.4886 0.2867 0.055 Uiso 1 1 calc R U . . .
H4B H 0.5973 0.4694 0.3636 0.055 Uiso 1 1 calc R U . . .
H4C H 0.7416 0.4301 0.4009 0.055 Uiso 1 1 calc R U . . .
C5 C 0.61151(8) 0.83596(7) 0.30429(6) 0.02324(12) Uani 1 1 d . . . . .
C6 C 0.51877(9) 0.86974(8) 0.20466(7) 0.02853(14) Uani 1 1 d . . . . .
H6 H 0.4625 0.8081 0.1204 0.034 Uiso 1 1 calc R U . . .
C7 C 0.51141(10) 0.99591(9) 0.23260(8) 0.03152(15) Uani 1 1 d . . . . .
H7 H 0.4497 1.0214 0.1663 0.038 Uiso 1 1 calc R U . . .
C8 C 0.59340(10) 1.08647(9) 0.35680(9) 0.03332(16) Uani 1 1 d . . . . .
H8 H 0.5864 1.1724 0.3728 0.040 Uiso 1 1 calc R U . . .
C9 C 0.68462(9) 1.05427(8) 0.45716(8) 0.03020(15) Uani 1 1 d . . . . .
H9 H 0.7389 1.1157 0.5414 0.036 Uiso 1 1 calc R U . . .
C10 C 0.69315(8) 0.92755(7) 0.42890(7) 0.02307(12) Uani 1 1 d . . . . .
C11 C 0.87063(9) 0.91411(8) 0.64077(7) 0.02697(14) Uani 1 1 d . . . . .
H11 H 0.9130 0.8451 0.6645 0.032 Uiso 1 1 calc R U . . .
C12 C 1.00339(11) 1.04576(10) 0.68236(10) 0.0453(2) Uani 1 1 d . . . . .
H12A H 1.0579 1.0317 0.6371 0.068 Uiso 1 1 calc R U . . .
H12B H 1.0720 1.0738 0.7736 0.068 Uiso 1 1 calc R U . . .
H12C H 0.9659 1.1167 0.6632 0.068 Uiso 1 1 calc R U . . .
C13 C 0.77955(14) 0.92738(13) 0.70634(9) 0.0449(2) Uani 1 1 d . . . . .
H13A H 0.7288 0.9882 0.6789 0.067 Uiso 1 1 calc R U . . .
H13B H 0.8474 0.9648 0.7981 0.067 Uiso 1 1 calc R U . . .
H13C H 0.7036 0.8377 0.6843 0.067 Uiso 1 1 calc R U . . .
C14 C 0.20394(8) 0.34069(7) 0.08975(6) 0.02196(12) Uani 1 1 d . . . . .
C15 C 0.33200(8) 0.38602(7) 0.06326(7) 0.02441(13) Uani 1 1 d . . . . .
H15 H 0.4168 0.4669 0.1366 0.029 Uiso 1 1 calc R U . . .
C16 C 0.27940(10) 0.42774(10) -0.05528(9) 0.03584(18) Uani 1 1 d . . . . .
H16A H 0.3610 0.4516 -0.0757 0.054 Uiso 1 1 calc R U . . .
H16B H 0.2534 0.5064 -0.0396 0.054 Uiso 1 1 calc R U . . .
H16C H 0.1902 0.3519 -0.1263 0.054 Uiso 1 1 calc R U . . .
C17 C 0.38920(10) 0.27319(8) 0.04752(9) 0.03450(17) Uani 1 1 d . . . . .
H17A H 0.3096 0.1957 -0.0279 0.052 Uiso 1 1 calc R U . . .
H17B H 0.4161 0.2444 0.1222 0.052 Uiso 1 1 calc R U . . .
H17C H 0.4786 0.3070 0.0381 0.052 Uiso 1 1 calc R U . . .
C18 C 0.00452(8) 0.21591(7) 0.08550(6) 0.02252(12) Uani 1 1 d . . . . .
C19 C -0.12124(9) 0.10790(8) 0.06399(7) 0.02706(14) Uani 1 1 d . . . . .
H19 H -0.1473 0.0179 0.0149 0.032 Uiso 1 1 calc R U . . .
C20 C -0.20663(9) 0.13652(9) 0.11666(8) 0.03053(15) Uani 1 1 d . . . . .
H20 H -0.2929 0.0649 0.1033 0.037 Uiso 1 1 calc R U . . .
C21 C -0.16795(10) 0.26926(9) 0.18932(8) 0.03203(16) Uani 1 1 d . . . . .
H21 H -0.2291 0.2856 0.2238 0.038 Uiso 1 1 calc R U . . .
C22 C -0.04259(9) 0.37765(8) 0.21231(8) 0.02928(14) Uani 1 1 d . . . . .
H22 H -0.0165 0.4673 0.2621 0.035 Uiso 1 1 calc R U . . .
C23 C 0.04342(8) 0.34895(7) 0.15893(6) 0.02268(12) Uani 1 1 d . . . . .
C24 C 0.25804(9) 0.57578(7) 0.22269(7) 0.02632(13) Uani 1 1 d . . . . .
H24 H 0.3411 0.6014 0.2017 0.032 Uiso 1 1 calc R U . . .
C25 C 0.16014(12) 0.65428(9) 0.17187(10) 0.0410(2) Uani 1 1 d . . . . .
H25A H 0.1148 0.6267 0.0797 0.061 Uiso 1 1 calc R U . . .
H25B H 0.2229 0.7519 0.2093 0.061 Uiso 1 1 calc R U . . .
H25C H 0.0798 0.6347 0.1940 0.061 Uiso 1 1 calc R U . . .
C26 C 0.33252(12) 0.61379(10) 0.36585(8) 0.03872(19) Uani 1 1 d . . . . .
H26A H 0.2543 0.5967 0.3905 0.058 Uiso 1 1 calc R U . . .
H26B H 0.3998 0.7103 0.4054 0.058 Uiso 1 1 calc R U . . .
H26C H 0.3914 0.5588 0.3939 0.058 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 1.3187(9) . ?
N1 C5 1.3868(9) . ?
N2 C1 1.3766(9) . ?
N2 C10 1.3887(9) . ?
N2 C11 1.4751(9) . ?
N3 C14 1.3153(9) . ?
N3 C18 1.3857(9) . ?
N4 C14 1.3824(9) . ?
N4 C23 1.3889(9) . ?
N4 C24 1.4701(9) . ?
C1 C2 1.5007(10) . ?
C2 C4 1.5240(11) . ?
C2 C3 1.5323(12) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.3979(10) . ?
C5 C10 1.4067(10) . ?
C6 C7 1.3851(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.3991(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.3869(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.3967(10) . ?
C9 H9 0.9500 . ?
C11 C13 1.5177(12) . ?
C11 C12 1.5193(13) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5001(10) . ?
C15 C17 1.5267(11) . ?
C15 C16 1.5327(11) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.3963(10) . ?
C18 C23 1.4069(9) . ?
C19 C20 1.3852(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.4015(12) . ?
C20 H20 0.9500 . ?
C21 C22 1.3894(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.3976(10) . ?
C22 H22 0.9500 . ?
C24 C26 1.5218(12) . ?
C24 C25 1.5237(12) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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 C5 104.87(6) . . ?
C1 N2 C10 106.24(6) . . ?
C1 N2 C11 126.99(6) . . ?
C10 N2 C11 126.72(6) . . ?
C14 N3 C18 105.08(6) . . ?
C14 N4 C23 106.19(6) . . ?
C14 N4 C24 126.35(6) . . ?
C23 N4 C24 127.46(6) . . ?
N1 C1 N2 113.37(6) . . ?
N1 C1 C2 123.69(6) . . ?
N2 C1 C2 122.86(6) . . ?
C1 C2 C4 111.01(6) . . ?
C1 C2 C3 109.69(7) . . ?
C4 C2 C3 110.61(7) . . ?
C1 C2 H2 108.5 . . ?
C4 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 129.24(7) . . ?
N1 C5 C10 110.22(6) . . ?
C6 C5 C10 120.54(7) . . ?
C7 C6 C5 117.96(7) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C8 121.07(7) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 121.86(7) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 117.09(7) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 H9 121.5 . . ?
N2 C10 C9 133.24(7) . . ?
N2 C10 C5 105.29(6) . . ?
C9 C10 C5 121.47(7) . . ?
N2 C11 C13 110.43(7) . . ?
N2 C11 C12 111.14(7) . . ?
C13 C11 C12 112.83(8) . . ?
N2 C11 H11 107.4 . . ?
C13 C11 H11 107.4 . . ?
C12 C11 H11 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 N4 113.21(6) . . ?
N3 C14 C15 123.11(6) . . ?
N4 C14 C15 123.63(6) . . ?
C14 C15 C17 110.41(6) . . ?
C14 C15 C16 109.52(6) . . ?
C17 C15 C16 111.06(7) . . ?
C14 C15 H15 108.6 . . ?
C17 C15 H15 108.6 . . ?
C16 C15 H15 108.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C19 128.74(6) . . ?
N3 C18 C23 110.28(6) . . ?
C19 C18 C23 120.98(7) . . ?
C20 C19 C18 117.71(7) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C19 C20 C21 121.17(7) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 121.81(7) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 117.07(7) . . ?
C21 C22 H22 121.5 . . ?
C23 C22 H22 121.5 . . ?
N4 C23 C22 133.51(7) . . ?
N4 C23 C18 105.24(6) . . ?
C22 C23 C18 121.25(7) . . ?
N4 C24 C26 111.11(7) . . ?
N4 C24 C25 111.55(7) . . ?
C26 C24 C25 112.36(7) . . ?
N4 C24 H24 107.2 . . ?
C26 C24 H24 107.2 . . ?
C25 C24 H24 107.2 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C5 N1 C1 N2 0.17(9) . . . . ?
C5 N1 C1 C2 -176.68(7) . . . . ?
C10 N2 C1 N1 0.24(9) . . . . ?
C11 N2 C1 N1 177.80(7) . . . . ?
C10 N2 C1 C2 177.12(7) . . . . ?
C11 N2 C1 C2 -5.32(12) . . . . ?
N1 C1 C2 C4 -25.90(11) . . . . ?
N2 C1 C2 C4 157.55(7) . . . . ?
N1 C1 C2 C3 96.64(9) . . . . ?
N2 C1 C2 C3 -79.91(9) . . . . ?
C1 N1 C5 C6 -179.63(8) . . . . ?
C1 N1 C5 C10 -0.51(8) . . . . ?
N1 C5 C6 C7 179.67(8) . . . . ?
C10 C5 C6 C7 0.63(12) . . . . ?
C5 C6 C7 C8 -0.45(13) . . . . ?
C6 C7 C8 C9 -0.32(14) . . . . ?
C7 C8 C9 C10 0.87(13) . . . . ?
C1 N2 C10 C9 179.39(8) . . . . ?
C11 N2 C10 C9 1.82(13) . . . . ?
C1 N2 C10 C5 -0.53(8) . . . . ?
C11 N2 C10 C5 -178.10(7) . . . . ?
C8 C9 C10 N2 179.42(8) . . . . ?
C8 C9 C10 C5 -0.67(12) . . . . ?
N1 C5 C10 N2 0.66(8) . . . . ?
C6 C5 C10 N2 179.86(7) . . . . ?
N1 C5 C10 C9 -179.27(7) . . . . ?
C6 C5 C10 C9 -0.07(11) . . . . ?
C1 N2 C11 C13 -111.87(9) . . . . ?
C10 N2 C11 C13 65.20(10) . . . . ?
C1 N2 C11 C12 122.12(9) . . . . ?
C10 N2 C11 C12 -60.80(10) . . . . ?
C18 N3 C14 N4 -0.01(8) . . . . ?
C18 N3 C14 C15 -177.55(6) . . . . ?
C23 N4 C14 N3 0.19(8) . . . . ?
C24 N4 C14 N3 -179.27(7) . . . . ?
C23 N4 C14 C15 177.72(6) . . . . ?
C24 N4 C14 C15 -1.74(11) . . . . ?
N3 C14 C15 C17 -32.21(10) . . . . ?
N4 C14 C15 C17 150.50(7) . . . . ?
N3 C14 C15 C16 90.39(9) . . . . ?
N4 C14 C15 C16 -86.90(8) . . . . ?
C14 N3 C18 C19 -179.71(7) . . . . ?
C14 N3 C18 C23 -0.19(8) . . . . ?
N3 C18 C19 C20 179.91(7) . . . . ?
C23 C18 C19 C20 0.43(11) . . . . ?
C18 C19 C20 C21 -0.16(12) . . . . ?
C19 C20 C21 C22 -0.28(13) . . . . ?
C20 C21 C22 C23 0.44(12) . . . . ?
C14 N4 C23 C22 179.88(8) . . . . ?
C24 N4 C23 C22 -0.66(13) . . . . ?
C14 N4 C23 C18 -0.29(7) . . . . ?
C24 N4 C23 C18 179.17(7) . . . . ?
C21 C22 C23 N4 179.65(8) . . . . ?
C21 C22 C23 C18 -0.16(11) . . . . ?
N3 C18 C23 N4 0.30(8) . . . . ?
C19 C18 C23 N4 179.87(7) . . . . ?
N3 C18 C23 C22 -179.84(7) . . . . ?
C19 C18 C23 C22 -0.28(11) . . . . ?
C14 N4 C24 C26 -114.64(8) . . . . ?
C23 N4 C24 C26 66.01(10) . . . . ?
C14 N4 C24 C25 119.14(8) . . . . ?
C23 N4 C24 C25 -60.21(10) . . . . ?

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
C24 H24 C5 1.00 2.84 3.6039(10) 133.5 .
C24 H24 N1 1.00 2.64 3.4972(10) 143.6 .
C19 H19 N3 0.95 2.69 3.5837(10) 156.1 2
C25 H25A C23 0.98 2.82 3.7235(13) 154.1 2_565

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040


_exptl_crystal_recrystallization_method Sublimation
