# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_DE2_143K
_database_code_depnum_ccdc_archive 'CCDC 1811066'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H30 N6'
_chemical_formula_moiety         'C26 H30 N6'
_chemical_formula_weight         426.56
_chemical_melting_point          551

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.1533(4)
_cell_length_b                   11.0888(4)
_cell_length_c                   18.0746(7)
_cell_angle_alpha                100.192(3)
_cell_angle_beta                 103.814(4)
_cell_angle_gamma                90.080(3)
_cell_volume                     1751.55(13)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    2678
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      30.13
_cell_measurement_temperature    143
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684.00
_exptl_absorpt_coefficient_mu    0.075
_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_correction_T_min  0.830
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      143
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            11335
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6055
_reflns_number_gt                3665
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1855
_refine_ls_wR_factor_gt          0.1530
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6055
_refine_ls_number_parameters     433
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0809P)²+0.5680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.2355(3) 0.4857(3) 0.08883(16) 0.0503(8) Uani 1 1 d . . . . .
N2 N 0.1446(3) 0.4855(2) 0.08663(13) 0.0365(7) Uani 1 1 d . . . . .
N3 N 0.7198(3) 0.4096(2) 0.35484(14) 0.0402(7) Uani 1 1 d . U . . .
N4 N 0.0885(3) 0.2190(2) 0.46132(15) 0.0399(7) Uani 1 1 d . . . . .
N5 N 0.4516(2) 0.1497(2) 0.44396(13) 0.0272(6) Uani 1 1 d . . . . .
N6 N 1.0465(3) 0.1573(2) 0.71945(13) 0.0317(6) Uani 1 1 d . . . . .
N7 N 0.5063(3) 0.0834(3) 0.25391(16) 0.0496(8) Uani 1 1 d . . . . .
N8 N 0.1439(3) 0.1457(2) 0.27278(13) 0.0311(6) Uani 1 1 d . . . . .
N9 N -0.4283(3) 0.1784(3) -0.00933(16) 0.0661(10) Uani 1 1 d . U . . .
C1 C -0.1329(4) 0.4866(3) 0.06271(16) 0.0368(8) Uani 1 1 d . . . . .
C2 C 0.0052(3) 0.4916(3) 0.03726(16) 0.0350(8) Uani 1 1 d . . . . .
C3 C 0.1554(3) 0.4633(3) 0.15632(16) 0.0347(8) Uani 1 1 d . . . . .
H3 H 0.0664 0.4515 0.1730 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2997(3) 0.4566(3) 0.20811(15) 0.0313(7) Uani 1 1 d . . . . .
C5 C 0.3106(3) 0.4266(3) 0.28154(16) 0.0323(7) Uani 1 1 d . . . . .
H5 H 0.2212 0.4141 0.2977 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4485(3) 0.4152(3) 0.33066(16) 0.0292(7) Uani 1 1 d . . . . .
H6 H 0.4517 0.3959 0.3802 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5840(3) 0.4311(3) 0.30950(16) 0.0304(7) Uani 1 1 d . . . . .
C8 C 0.5730(3) 0.4676(3) 0.23660(16) 0.0362(8) Uani 1 1 d . . . . .
H8 H 0.6621 0.4848 0.2214 0.043 Uiso 1 1 calc R U . . .
C9 C 0.4353(3) 0.4780(3) 0.18846(16) 0.0352(8) Uani 1 1 d . . . . .
H9 H 0.4315 0.5006 0.1398 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7303(3) 0.3681(3) 0.42820(17) 0.0389(8) Uani 1 1 d . . . . .
H10A H 0.8253 0.3251 0.4408 0.047 Uiso 1 1 calc R U . . .
H10B H 0.6462 0.3076 0.4210 0.047 Uiso 1 1 calc R U . . .
C11 C 0.7263(4) 0.4675(3) 0.49664(18) 0.0480(9) Uani 1 1 d . . . . .
H11A H 0.7340 0.4307 0.5428 0.058 Uiso 1 1 calc R U . . .
H11B H 0.8110 0.5268 0.5057 0.058 Uiso 1 1 calc R U . . .
H11C H 0.6314 0.5093 0.4858 0.058 Uiso 1 1 calc R U . . .
C12 C 0.8636(3) 0.4320(3) 0.33419(19) 0.0417(8) Uani 1 1 d . U . . .
H12A H 0.8514 0.4024 0.2780 0.050 Uiso 1 1 calc R U . . .
H12B H 0.9429 0.3848 0.3624 0.050 Uiso 1 1 calc R U . . .
C13 C 0.9120(4) 0.5641(3) 0.3534(2) 0.0537(10) Uani 1 1 d . . . . .
H13A H 1.0071 0.5750 0.3389 0.064 Uiso 1 1 calc R U . . .
H13B H 0.8347 0.6111 0.3248 0.064 Uiso 1 1 calc R U . . .
H13C H 0.9262 0.5935 0.4092 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1831(3) 0.1914(3) 0.43065(16) 0.0284(7) Uani 1 1 d . . . . .
C15 C 0.3094(3) 0.1573(2) 0.39750(15) 0.0253(7) Uani 1 1 d . . . . .
C16 C 0.4797(3) 0.1886(3) 0.51803(15) 0.0273(7) Uani 1 1 d . . . . .
H16 H 0.4009 0.2233 0.5396 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6248(3) 0.1816(3) 0.56889(15) 0.0273(7) Uani 1 1 d . . . . .
C18 C 0.6553(3) 0.2369(3) 0.64663(15) 0.0302(7) Uani 1 1 d . . . . .
H18 H 0.5787 0.2803 0.6660 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7939(3) 0.2302(3) 0.69624(16) 0.0311(7) Uani 1 1 d . . . . .
H19 H 0.8115 0.2703 0.7488 0.037 Uiso 1 1 calc R U . . .
C20 C 0.9095(3) 0.1653(3) 0.67067(15) 0.0264(7) Uani 1 1 d . . . . .
C21 C 0.8781(3) 0.1094(3) 0.59135(15) 0.0273(7) Uani 1 1 d . . . . .
H21 H 0.9539 0.0652 0.5718 0.033 Uiso 1 1 calc R U . . .
C22 C 0.7406(3) 0.1179(3) 0.54263(15) 0.0278(7) Uani 1 1 d . . . . .
H22 H 0.7230 0.0798 0.4897 0.033 Uiso 1 1 calc R U . . .
C23 C 1.0909(3) 0.2348(3) 0.79625(15) 0.0342(8) Uani 1 1 d . . . . .
H23A H 1.0444 0.3150 0.7940 0.041 Uiso 1 1 calc R U . . .
H23B H 1.2016 0.2498 0.8104 0.041 Uiso 1 1 calc R U . . .
C24 C 1.0458(4) 0.1796(3) 0.85910(17) 0.0465(9) Uani 1 1 d . . . . .
H24A H 1.0787 0.2358 0.9089 0.056 Uiso 1 1 calc R U . . .
H24B H 0.9361 0.1663 0.8463 0.056 Uiso 1 1 calc R U . . .
H24C H 1.0934 0.1010 0.8627 0.056 Uiso 1 1 calc R U . . .
C25 C 1.1573(3) 0.0721(3) 0.69781(16) 0.0341(8) Uani 1 1 d . . . . .
H25A H 1.1035 -0.0017 0.6627 0.041 Uiso 1 1 calc R U . . .
H25B H 1.2173 0.0458 0.7450 0.041 Uiso 1 1 calc R U . . .
C26 C 1.2632(3) 0.1263(3) 0.65812(17) 0.0382(8) Uani 1 1 d . . . . .
H26A H 1.3344 0.0649 0.6452 0.046 Uiso 1 1 calc R U . . .
H26B H 1.2049 0.1507 0.6106 0.046 Uiso 1 1 calc R U . . .
H26C H 1.3188 0.1982 0.6930 0.046 Uiso 1 1 calc R U . . .
C27 C 0.4124(4) 0.1048(3) 0.28531(16) 0.0340(8) Uani 1 1 d . . . . .
C28 C 0.2854(3) 0.1347(3) 0.31870(15) 0.0285(7) Uani 1 1 d . . . . .
C29 C 0.1251(3) 0.1346(3) 0.19829(16) 0.0357(8) Uani 1 1 d . . . . .
H29 H 0.2096 0.1171 0.1768 0.043 Uiso 1 1 calc R U . . .
C30 C -0.0175(3) 0.1478(3) 0.14725(15) 0.0321(7) Uani 1 1 d . . . . .
C31 C -0.0300(4) 0.1300(3) 0.06698(17) 0.0436(9) Uani 1 1 d . . . . .
H31 H 0.0571 0.1115 0.0479 0.052 Uiso 1 1 calc R U . . .
C32 C -0.1645(4) 0.1385(3) 0.01560(17) 0.0462(9) Uani 1 1 d . . . . .
H32 H -0.1695 0.1239 -0.0384 0.055 Uiso 1 1 calc R U . . .
C33 C -0.2938(3) 0.1682(3) 0.04089(17) 0.0410(8) Uani 1 1 d . . . . .
C34 C -0.2817(4) 0.1858(3) 0.12188(17) 0.0403(8) Uani 1 1 d . . . . .
H34 H -0.3680 0.2063 0.1412 0.048 Uiso 1 1 calc R U . . .
C35 C -0.1482(3) 0.1737(3) 0.17215(16) 0.0319(7) Uani 1 1 d . . . . .
H35 H -0.1443 0.1832 0.2259 0.038 Uiso 1 1 calc R U . . .
C36 C -0.4517(4) 0.1335(4) -0.09374(18) 0.0537(10) Uani 1 1 d . . . . .
H36A H -0.5563 0.0993 -0.1151 0.064 Uiso 1 1 calc R U . . .
H36B H -0.3830 0.0663 -0.1022 0.064 Uiso 1 1 calc R U . . .
C37 C -0.4245(4) 0.2310(4) -0.1362(2) 0.0593(11) Uani 1 1 d . . . . .
H37A H -0.4415 0.1965 -0.1916 0.071 Uiso 1 1 calc R U . . .
H37B H -0.4937 0.2970 -0.1291 0.071 Uiso 1 1 calc R U . . .
H37C H -0.3204 0.2640 -0.1162 0.071 Uiso 1 1 calc R U . . .
C38 C -0.5496(5) 0.2612(4) 0.0187(2) 0.0645(11) Uani 1 1 d . U . . .
H38A H -0.5025 0.3240 0.0645 0.077 Uiso 1 1 calc R U . . .
H38B H -0.6052 0.3028 -0.0229 0.077 Uiso 1 1 calc R U . . .
C39 C -0.6454(6) 0.1800(5) 0.0377(3) 0.118(2) Uani 1 1 d . U . . .
H39A H -0.7256 0.2254 0.0561 0.141 Uiso 1 1 calc R U . . .
H39B H -0.6900 0.1183 -0.0082 0.141 Uiso 1 1 calc R U . . .
H39C H -0.5880 0.1393 0.0787 0.141 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.148(4) . ?
N2 C3 1.307(3) . ?
N2 C2 1.381(3) . ?
N3 C7 1.363(3) . ?
N3 C10 1.461(3) . ?
N3 C12 1.483(4) . ?
N4 C14 1.149(4) . ?
N5 C16 1.295(3) . ?
N5 C15 1.382(3) . ?
N6 C20 1.363(3) . ?
N6 C25 1.461(4) . ?
N6 C23 1.462(4) . ?
N7 C27 1.141(4) . ?
N8 C29 1.299(4) . ?
N8 C28 1.380(3) . ?
N9 C33 1.362(4) . ?
N9 C36 1.482(4) . ?
N9 C38 1.562(5) . ?
C1 C2 1.449(5) . ?
C2 C2 1.373(5) 2_565 ?
C3 C4 1.435(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.401(4) . ?
C4 C5 1.405(4) . ?
C5 C6 1.379(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.427(4) . ?
C8 C9 1.368(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.512(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.486(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.446(4) . ?
C15 C28 1.365(4) . ?
C16 C17 1.434(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(4) . ?
C17 C22 1.404(4) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.403(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.418(4) . ?
C21 C22 1.367(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.518(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.516(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.446(4) . ?
C29 C30 1.431(4) . ?
C29 H29 0.9500 . ?
C30 C35 1.389(4) . ?
C30 C31 1.406(4) . ?
C31 C32 1.369(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.387(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.420(4) . ?
C34 C35 1.360(4) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.486(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.396(6) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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
C3 N2 C2 120.5(3) . . ?
C7 N3 C10 121.0(3) . . ?
C7 N3 C12 122.1(2) . . ?
C10 N3 C12 116.9(2) . . ?
C16 N5 C15 120.6(3) . . ?
C20 N6 C25 122.1(2) . . ?
C20 N6 C23 121.6(2) . . ?
C25 N6 C23 116.4(2) . . ?
C29 N8 C28 119.6(3) . . ?
C33 N9 C36 121.2(3) . . ?
C33 N9 C38 119.8(3) . . ?
C36 N9 C38 117.8(2) . . ?
N1 C1 C2 174.5(3) . . ?
C2 C2 N2 120.1(4) 2_565 . ?
C2 C2 C1 118.0(3) 2_565 . ?
N2 C2 C1 121.8(2) . . ?
N2 C3 C4 121.0(3) . . ?
N2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C9 C4 C5 116.8(3) . . ?
C9 C4 C3 122.5(3) . . ?
C5 C4 C3 120.8(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
N3 C7 C6 122.1(2) . . ?
N3 C7 C8 121.1(3) . . ?
C6 C7 C8 116.7(2) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 122.6(3) . . ?
C8 C9 H9 118.7 . . ?
C4 C9 H9 118.7 . . ?
N3 C10 C11 115.6(3) . . ?
N3 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
N3 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 112.0(3) . . ?
N3 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N3 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C15 175.9(3) . . ?
C28 C15 N5 120.5(3) . . ?
C28 C15 C14 118.3(2) . . ?
N5 C15 C14 121.2(2) . . ?
N5 C16 C17 122.8(3) . . ?
N5 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C18 C17 C22 117.5(2) . . ?
C18 C17 C16 120.9(3) . . ?
C22 C17 C16 121.6(3) . . ?
C19 C18 C17 121.5(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
N6 C20 C19 121.7(3) . . ?
N6 C20 C21 121.3(3) . . ?
C19 C20 C21 117.0(2) . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C17 121.6(3) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
N6 C23 C24 113.6(3) . . ?
N6 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N6 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C25 C26 113.5(2) . . ?
N6 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
N6 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N7 C27 C28 174.8(3) . . ?
C15 C28 N8 120.1(3) . . ?
C15 C28 C27 118.5(2) . . ?
N8 C28 C27 121.3(2) . . ?
N8 C29 C30 122.7(3) . . ?
N8 C29 H29 118.6 . . ?
C30 C29 H29 118.6 . . ?
C35 C30 C31 117.0(3) . . ?
C35 C30 C29 123.6(3) . . ?
C31 C30 C29 119.4(3) . . ?
C32 C31 C30 121.6(3) . . ?
C32 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
C31 C32 C33 121.2(3) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
N9 C33 C32 122.0(3) . . ?
N9 C33 C34 120.7(3) . . ?
C32 C33 C34 117.3(3) . . ?
C35 C34 C33 120.9(3) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C34 C35 C30 121.9(3) . . ?
C34 C35 H35 119.0 . . ?
C30 C35 H35 119.0 . . ?
N9 C36 C37 112.9(3) . . ?
N9 C36 H36A 109.0 . . ?
C37 C36 H36A 109.0 . . ?
N9 C36 H36B 109.0 . . ?
C37 C36 H36B 109.0 . . ?
H36A C36 H36B 107.8 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 N9 104.5(4) . . ?
C39 C38 H38A 110.9 . . ?
N9 C38 H38A 110.9 . . ?
C39 C38 H38B 110.9 . . ?
N9 C38 H38B 110.9 . . ?
H38A C38 H38B 108.9 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
C3 N2 C2 C2 -176.5(4) . . . 2_565 ?
C3 N2 C2 C1 6.5(5) . . . . ?
C2 N2 C3 C4 179.9(3) . . . . ?
N2 C3 C4 C9 2.6(5) . . . . ?
N2 C3 C4 C5 -176.8(3) . . . . ?
C9 C4 C5 C6 -2.0(4) . . . . ?
C3 C4 C5 C6 177.4(3) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
C10 N3 C7 C6 0.2(5) . . . . ?
C12 N3 C7 C6 -177.1(3) . . . . ?
C10 N3 C7 C8 -177.8(3) . . . . ?
C12 N3 C7 C8 4.8(5) . . . . ?
C5 C6 C7 N3 -174.2(3) . . . . ?
C5 C6 C7 C8 3.9(4) . . . . ?
N3 C7 C8 C9 174.0(3) . . . . ?
C6 C7 C8 C9 -4.2(4) . . . . ?
C7 C8 C9 C4 1.5(5) . . . . ?
C5 C4 C9 C8 1.7(5) . . . . ?
C3 C4 C9 C8 -177.7(3) . . . . ?
C7 N3 C10 C11 -82.0(4) . . . . ?
C12 N3 C10 C11 95.5(3) . . . . ?
C7 N3 C12 C13 78.9(4) . . . . ?
C10 N3 C12 C13 -98.5(3) . . . . ?
C16 N5 C15 C28 169.5(3) . . . . ?
C16 N5 C15 C14 -9.3(4) . . . . ?
C15 N5 C16 C17 179.3(2) . . . . ?
N5 C16 C17 C18 172.6(3) . . . . ?
N5 C16 C17 C22 -8.1(4) . . . . ?
C22 C17 C18 C19 0.3(4) . . . . ?
C16 C17 C18 C19 179.6(3) . . . . ?
C17 C18 C19 C20 -1.2(4) . . . . ?
C25 N6 C20 C19 168.3(3) . . . . ?
C23 N6 C20 C19 -12.2(4) . . . . ?
C25 N6 C20 C21 -12.5(4) . . . . ?
C23 N6 C20 C21 167.0(3) . . . . ?
C18 C19 C20 N6 -179.5(3) . . . . ?
C18 C19 C20 C21 1.3(4) . . . . ?
N6 C20 C21 C22 -179.8(3) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C17 -0.3(4) . . . . ?
C18 C17 C22 C21 0.5(4) . . . . ?
C16 C17 C22 C21 -178.9(3) . . . . ?
C20 N6 C23 C24 88.8(3) . . . . ?
C25 N6 C23 C24 -91.8(3) . . . . ?
C20 N6 C25 C26 89.9(3) . . . . ?
C23 N6 C25 C26 -89.5(3) . . . . ?
N5 C15 C28 N8 -178.3(2) . . . . ?
C14 C15 C28 N8 0.6(4) . . . . ?
N5 C15 C28 C27 -1.0(4) . . . . ?
C14 C15 C28 C27 177.9(3) . . . . ?
C29 N8 C28 C15 174.0(3) . . . . ?
C29 N8 C28 C27 -3.3(4) . . . . ?
C28 N8 C29 C30 -178.5(3) . . . . ?
N8 C29 C30 C35 0.2(5) . . . . ?
N8 C29 C30 C31 -177.6(3) . . . . ?
C35 C30 C31 C32 0.4(5) . . . . ?
C29 C30 C31 C32 178.4(3) . . . . ?
C30 C31 C32 C33 1.6(6) . . . . ?
C36 N9 C33 C32 12.9(6) . . . . ?
C38 N9 C33 C32 -154.6(4) . . . . ?
C36 N9 C33 C34 -166.0(3) . . . . ?
C38 N9 C33 C34 26.5(5) . . . . ?
C31 C32 C33 N9 179.3(4) . . . . ?
C31 C32 C33 C34 -1.8(5) . . . . ?
N9 C33 C34 C35 178.9(3) . . . . ?
C32 C33 C34 C35 -0.1(5) . . . . ?
C33 C34 C35 C30 2.1(5) . . . . ?
C31 C30 C35 C34 -2.3(5) . . . . ?
C29 C30 C35 C34 179.8(3) . . . . ?
C33 N9 C36 C37 -94.5(4) . . . . ?
C38 N9 C36 C37 73.3(4) . . . . ?
C33 N9 C38 C39 -96.8(4) . . . . ?
C36 N9 C38 C39 95.3(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"N, N'-bis [(4-diethylaminophenyl) methylidene] diaminomaleonitrile"
_chemical_name_common            DE2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/diethyl ether'
####################################################################### 
# 
# 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_DE2_243K
_database_code_depnum_ccdc_archive 'CCDC 1811069'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H30 N6'
_chemical_formula_moiety         'C26 H30 N6'
_chemical_formula_weight         426.56
_chemical_melting_point          551

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.1764(4)
_cell_length_b                   11.1823(4)
_cell_length_c                   18.1079(7)
_cell_angle_alpha                79.869(3)
_cell_angle_beta                 76.150(3)
_cell_angle_gamma                89.880(3)
_cell_volume                     1774.40(12)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    2474
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      30.06
_cell_measurement_temperature    243
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684.00
_exptl_absorpt_coefficient_mu    0.074
_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_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      243
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            11551
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6158
_reflns_number_gt                3181
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1548
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2265
_refine_ls_wR_factor_gt          0.1777
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6158
_refine_ls_number_parameters     433
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0990P)²+0.2630P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.2326(4) 0.5127(3) 0.0897(2) 0.0735(11) Uani 1 1 d . . . . .
N2 N 0.8552(3) 0.5135(3) 0.08631(16) 0.0514(8) Uani 1 1 d . . . . .
N3 N 0.2809(3) 0.5865(3) 0.35425(17) 0.0653(10) Uani 1 1 d . U . . .
N4 N 0.9099(4) 0.7804(3) 0.46055(19) 0.0634(10) Uani 1 1 d . . . . .
N5 N 0.5484(3) 0.8498(2) 0.44325(15) 0.0414(7) Uani 1 1 d . . . . .
N6 N -0.0438(3) 0.8427(3) 0.71830(16) 0.0504(8) Uani 1 1 d . . . . .
N7 N 0.4944(4) 0.9160(4) 0.2543(2) 0.0788(12) Uani 1 1 d . . . . .
N8 N 0.8556(3) 0.8543(3) 0.27260(15) 0.0457(8) Uani 1 1 d . . . . .
N9 N 1.4248(4) 0.8215(5) -0.00849(19) 0.0999(15) Uani 1 1 d . U . . .
C1 C 1.1313(5) 0.5124(4) 0.0632(2) 0.0539(11) Uani 1 1 d . . . . .
C2 C 0.9947(4) 0.5084(3) 0.03731(18) 0.0479(9) Uani 1 1 d . . . . .
C3 C 0.8436(4) 0.5361(3) 0.15573(19) 0.0507(10) Uani 1 1 d . . . . .
H3 H 0.9310 0.5487 0.1723 0.061 Uiso 1 1 calc R U . . .
C4 C 0.6995(4) 0.5421(3) 0.20702(18) 0.0430(9) Uani 1 1 d . . . . .
C5 C 0.6888(4) 0.5742(3) 0.27959(19) 0.0487(9) Uani 1 1 d . . . . .
H5 H 0.7773 0.5889 0.2947 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5520(4) 0.5845(3) 0.32900(19) 0.0478(9) Uani 1 1 d . . . . .
H6 H 0.5490 0.6048 0.3775 0.057 Uiso 1 1 calc R U . . .
C7 C 0.4166(4) 0.5654(3) 0.30866(19) 0.0468(9) Uani 1 1 d . . . . .
C8 C 0.4289(4) 0.5300(4) 0.23659(19) 0.0581(11) Uani 1 1 d . . . . .
H8 H 0.3411 0.5130 0.2215 0.070 Uiso 1 1 calc R U . . .
C9 C 0.5656(4) 0.5197(3) 0.18809(19) 0.0528(10) Uani 1 1 d . . . . .
H9 H 0.5690 0.4967 0.1402 0.063 Uiso 1 1 calc R U . . .
C10 C 0.2695(4) 0.6295(4) 0.4275(2) 0.0616(12) Uani 1 1 d . . . . .
H10A H 0.1750 0.6711 0.4396 0.074 Uiso 1 1 calc R U . . .
H10B H 0.3516 0.6898 0.4198 0.074 Uiso 1 1 calc R U . . .
C11 C 0.2750(5) 0.5341(4) 0.4961(2) 0.0819(15) Uani 1 1 d . . . . .
H11A H 0.2666 0.5719 0.5411 0.098 Uiso 1 1 calc R U . . .
H11B H 0.1924 0.4749 0.5057 0.098 Uiso 1 1 calc R U . . .
H11C H 0.3694 0.4937 0.4859 0.098 Uiso 1 1 calc R U . . .
C12 C 0.1356(4) 0.5660(4) 0.3328(2) 0.0684(12) Uani 1 1 d . U . . .
H12A H 0.0568 0.6123 0.3606 0.082 Uiso 1 1 calc R U . . .
H12B H 0.1477 0.5940 0.2772 0.082 Uiso 1 1 calc R U . . .
C13 C 0.0940(6) 0.4403(4) 0.3525(3) 0.0952(17) Uani 1 1 d . . . . .
H13A H 0.0002 0.4266 0.3387 0.114 Uiso 1 1 calc R U . . .
H13B H 0.1719 0.3949 0.3244 0.114 Uiso 1 1 calc R U . . .
H13C H 0.0813 0.4132 0.4076 0.114 Uiso 1 1 calc R U . . .
C14 C 0.8159(4) 0.8077(3) 0.43000(19) 0.0446(9) Uani 1 1 d . . . . .
C15 C 0.6905(4) 0.8421(3) 0.39708(18) 0.0392(8) Uani 1 1 d . . . . .
C16 C 0.5214(4) 0.8105(3) 0.51703(18) 0.0417(9) Uani 1 1 d . . . . .
H16 H 0.5990 0.7752 0.5381 0.050 Uiso 1 1 calc R U . . .
C17 C 0.3762(4) 0.8192(3) 0.56779(18) 0.0393(8) Uani 1 1 d . . . . .
C18 C 0.3465(4) 0.7635(3) 0.64551(18) 0.0451(9) Uani 1 1 d . . . . .
H18 H 0.4223 0.7209 0.6644 0.054 Uiso 1 1 calc R U . . .
C19 C 0.2090(4) 0.7698(3) 0.69457(19) 0.0453(9) Uani 1 1 d . . . . .
H19 H 0.1916 0.7296 0.7462 0.054 Uiso 1 1 calc R U . . .
C20 C 0.0928(4) 0.8350(3) 0.66960(17) 0.0391(8) Uani 1 1 d . . . . .
C21 C 0.1231(4) 0.8896(3) 0.59053(18) 0.0425(9) Uani 1 1 d . . . . .
H21 H 0.0480 0.9325 0.5712 0.051 Uiso 1 1 calc R U . . .
C22 C 0.2606(4) 0.8808(3) 0.54173(18) 0.0421(9) Uani 1 1 d . . . . .
H22 H 0.2773 0.9172 0.4894 0.050 Uiso 1 1 calc R U . . .
C23 C -0.0859(4) 0.7662(3) 0.79487(19) 0.0509(10) Uani 1 1 d . . . . .
H23A H -0.0383 0.6880 0.7924 0.061 Uiso 1 1 calc R U . . .
H23B H -0.1949 0.7503 0.8091 0.061 Uiso 1 1 calc R U . . .
C24 C -0.0420(5) 0.8209(4) 0.8570(2) 0.0714(13) Uani 1 1 d . . . . .
H24A H -0.0732 0.7655 0.9060 0.086 Uiso 1 1 calc R U . . .
H24B H 0.0661 0.8350 0.8441 0.086 Uiso 1 1 calc R U . . .
H24C H -0.0907 0.8974 0.8608 0.086 Uiso 1 1 calc R U . . .
C25 C -0.1544(4) 0.9272(3) 0.6968(2) 0.0511(10) Uani 1 1 d . . . . .
H25A H -0.1016 0.9989 0.6614 0.061 Uiso 1 1 calc R U . . .
H25B H -0.2129 0.9541 0.7433 0.061 Uiso 1 1 calc R U . . .
C26 C -0.2602(4) 0.8728(4) 0.6585(2) 0.0606(11) Uani 1 1 d . . . . .
H26A H -0.3308 0.9329 0.6456 0.073 Uiso 1 1 calc R U . . .
H26B H -0.2034 0.8477 0.6117 0.073 Uiso 1 1 calc R U . . .
H26C H -0.3148 0.8028 0.6936 0.073 Uiso 1 1 calc R U . . .
C27 C 0.5872(5) 0.8944(4) 0.2856(2) 0.0530(10) Uani 1 1 d . . . . .
C28 C 0.7136(4) 0.8646(3) 0.31861(18) 0.0434(9) Uani 1 1 d . . . . .
C29 C 0.8740(4) 0.8648(3) 0.19859(19) 0.0513(10) Uani 1 1 d . . . . .
H29 H 0.7906 0.8818 0.1774 0.062 Uiso 1 1 calc R U . . .
C30 C 1.0160(4) 0.8516(3) 0.14773(18) 0.0475(9) Uani 1 1 d . . . . .
C31 C 1.0280(4) 0.8677(4) 0.0680(2) 0.0700(13) Uani 1 1 d . . . . .
H31 H 0.9417 0.8844 0.0492 0.084 Uiso 1 1 calc R U . . .
C32 C 1.1625(4) 0.8595(4) 0.0168(2) 0.0697(13) Uani 1 1 d . . . . .
H32 H 1.1676 0.8737 -0.0365 0.084 Uiso 1 1 calc R U . . .
C33 C 1.2911(4) 0.8306(4) 0.0421(2) 0.0612(12) Uani 1 1 d . . . . .
C34 C 1.2788(4) 0.8162(4) 0.12199(19) 0.0570(11) Uani 1 1 d . . . . .
H34 H 1.3644 0.7979 0.1411 0.068 Uiso 1 1 calc R U . . .
C35 C 1.1460(4) 0.8280(3) 0.17211(18) 0.0467(9) Uani 1 1 d . . . . .
H35 H 1.1426 0.8199 0.2251 0.056 Uiso 1 1 calc R U . . .
C36 C 1.4488(5) 0.8653(5) -0.0928(2) 0.0837(15) Uani 1 1 d . . . . .
H36A H 1.3809 0.9313 -0.1015 0.100 Uiso 1 1 calc R U . . .
H36B H 1.5520 0.8986 -0.1138 0.100 Uiso 1 1 calc R U . . .
C37 C 1.4233(6) 0.7715(5) -0.1339(3) 0.1033(19) Uani 1 1 d . . . . .
H37A H 1.4405 0.8052 -0.1886 0.124 Uiso 1 1 calc R U . . .
H37B H 1.4918 0.7067 -0.1266 0.124 Uiso 1 1 calc R U . . .
H37C H 1.3206 0.7394 -0.1143 0.124 Uiso 1 1 calc R U . . .
C38 C 1.5504(6) 0.7393(6) 0.0205(3) 0.0995(17) Uani 1 1 d D U . . .
H38A H 1.5074 0.6808 0.0678 0.119 Uiso 1 1 calc R U . . .
H38B H 1.6057 0.6961 -0.0195 0.119 Uiso 1 1 calc R U . . .
C39 C 1.6379(8) 0.8275(7) 0.0336(4) 0.189(4) Uani 1 1 d D . . . .
H39A H 1.7215 0.7908 0.0520 0.227 Uiso 1 1 calc R U . . .
H39B H 1.6759 0.8849 -0.0141 0.227 Uiso 1 1 calc R U . . .
H39C H 1.5786 0.8697 0.0723 0.227 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.144(5) . ?
N2 C3 1.305(4) . ?
N2 C2 1.380(4) . ?
N3 C7 1.365(4) . ?
N3 C10 1.468(4) . ?
N3 C12 1.504(5) . ?
N4 C14 1.145(5) . ?
N5 C16 1.294(4) . ?
N5 C15 1.382(4) . ?
N6 C20 1.361(4) . ?
N6 C25 1.459(4) . ?
N6 C23 1.460(4) . ?
N7 C27 1.134(5) . ?
N8 C29 1.294(4) . ?
N8 C28 1.385(4) . ?
N9 C33 1.360(4) . ?
N9 C36 1.482(6) . ?
N9 C38 1.601(6) . ?
C1 C2 1.443(6) . ?
C2 C2 1.377(6) 2_765 ?
C3 C4 1.431(4) . ?
C3 H3 0.9400 . ?
C4 C9 1.387(5) . ?
C4 C5 1.403(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.405(5) . ?
C6 H6 0.9400 . ?
C7 C8 1.408(4) . ?
C8 C9 1.366(4) . ?
C8 H8 0.9400 . ?
C9 H9 0.9400 . ?
C10 C11 1.499(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C13 1.418(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C15 1.440(5) . ?
C15 C28 1.363(4) . ?
C16 C17 1.441(4) . ?
C16 H16 0.9400 . ?
C17 C22 1.395(5) . ?
C17 C18 1.397(5) . ?
C18 C19 1.368(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.409(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.415(4) . ?
C21 C22 1.370(4) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
C23 C24 1.503(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 C26 1.505(5) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C27 C28 1.441(5) . ?
C29 C30 1.428(4) . ?
C29 H29 0.9400 . ?
C30 C35 1.377(5) . ?
C30 C31 1.401(5) . ?
C31 C32 1.369(5) . ?
C31 H31 0.9400 . ?
C32 C33 1.383(5) . ?
C32 H32 0.9400 . ?
C33 C34 1.403(5) . ?
C34 C35 1.356(4) . ?
C34 H34 0.9400 . ?
C35 H35 0.9400 . ?
C36 C37 1.437(6) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 H37C 0.9700 . ?
C38 C39 1.360(7) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 H39C 0.9700 . ?

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
C3 N2 C2 120.3(3) . . ?
C7 N3 C10 121.4(3) . . ?
C7 N3 C12 122.0(3) . . ?
C10 N3 C12 116.5(3) . . ?
C16 N5 C15 119.9(3) . . ?
C20 N6 C25 121.9(3) . . ?
C20 N6 C23 121.1(3) . . ?
C25 N6 C23 117.0(3) . . ?
C29 N8 C28 119.5(3) . . ?
C33 N9 C36 122.1(4) . . ?
C33 N9 C38 119.3(4) . . ?
C36 N9 C38 117.6(3) . . ?
N1 C1 C2 174.4(4) . . ?
C2 C2 N2 119.7(4) 2_765 . ?
C2 C2 C1 118.3(4) 2_765 . ?
N2 C2 C1 121.9(3) . . ?
N2 C3 C4 120.9(4) . . ?
N2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C9 C4 C5 116.8(3) . . ?
C9 C4 C3 123.0(3) . . ?
C5 C4 C3 120.2(3) . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
N3 C7 C6 121.8(3) . . ?
N3 C7 C8 121.7(4) . . ?
C6 C7 C8 116.3(3) . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C4 122.2(3) . . ?
C8 C9 H9 118.9 . . ?
C4 C9 H9 118.9 . . ?
N3 C10 C11 116.2(3) . . ?
N3 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
N3 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N3 109.2(4) . . ?
C13 C12 H12A 109.8 . . ?
N3 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
N3 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C15 175.8(3) . . ?
C28 C15 N5 120.0(3) . . ?
C28 C15 C14 118.6(3) . . ?
N5 C15 C14 121.4(3) . . ?
N5 C16 C17 122.0(3) . . ?
N5 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C22 C17 C18 117.8(3) . . ?
C22 C17 C16 122.0(3) . . ?
C18 C17 C16 120.2(3) . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 121.6(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
N6 C20 C19 122.0(3) . . ?
N6 C20 C21 121.3(3) . . ?
C19 C20 C21 116.7(3) . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C17 121.7(3) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
N6 C23 C24 113.9(3) . . ?
N6 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N6 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C25 C26 113.2(3) . . ?
N6 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
N6 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N7 C27 C28 174.6(4) . . ?
C15 C28 N8 119.8(3) . . ?
C15 C28 C27 118.6(3) . . ?
N8 C28 C27 121.5(3) . . ?
N8 C29 C30 122.7(4) . . ?
N8 C29 H29 118.7 . . ?
C30 C29 H29 118.7 . . ?
C35 C30 C31 116.9(3) . . ?
C35 C30 C29 123.7(3) . . ?
C31 C30 C29 119.3(3) . . ?
C32 C31 C30 121.4(4) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C31 C32 C33 121.1(3) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
N9 C33 C32 121.3(3) . . ?
N9 C33 C34 121.5(4) . . ?
C32 C33 C34 117.1(3) . . ?
C35 C34 C33 121.4(4) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C34 C35 C30 122.0(3) . . ?
C34 C35 H35 119.0 . . ?
C30 C35 H35 119.0 . . ?
C37 C36 N9 113.0(4) . . ?
C37 C36 H36A 109.0 . . ?
N9 C36 H36A 109.0 . . ?
C37 C36 H36B 109.0 . . ?
N9 C36 H36B 109.0 . . ?
H36A C36 H36B 107.8 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 N9 99.6(6) . . ?
C39 C38 H38A 111.9 . . ?
N9 C38 H38A 111.9 . . ?
C39 C38 H38B 111.9 . . ?
N9 C38 H38B 111.9 . . ?
H38A C38 H38B 109.6 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
C3 N2 C2 C2 -176.1(4) . . . 2_765 ?
C3 N2 C2 C1 7.9(5) . . . . ?
C2 N2 C3 C4 179.8(3) . . . . ?
N2 C3 C4 C9 2.7(6) . . . . ?
N2 C3 C4 C5 -175.9(3) . . . . ?
C9 C4 C5 C6 -0.9(5) . . . . ?
C3 C4 C5 C6 177.9(3) . . . . ?
C4 C5 C6 C7 -1.1(6) . . . . ?
C10 N3 C7 C6 -0.5(6) . . . . ?
C12 N3 C7 C6 -179.9(4) . . . . ?
C10 N3 C7 C8 -176.8(4) . . . . ?
C12 N3 C7 C8 3.8(6) . . . . ?
C5 C6 C7 N3 -173.8(4) . . . . ?
C5 C6 C7 C8 2.7(5) . . . . ?
N3 C7 C8 C9 174.0(4) . . . . ?
C6 C7 C8 C9 -2.6(6) . . . . ?
C7 C8 C9 C4 0.7(6) . . . . ?
C5 C4 C9 C8 1.1(6) . . . . ?
C3 C4 C9 C8 -177.7(4) . . . . ?
C7 N3 C10 C11 -81.9(5) . . . . ?
C12 N3 C10 C11 97.5(4) . . . . ?
C7 N3 C12 C13 80.0(5) . . . . ?
C10 N3 C12 C13 -99.4(4) . . . . ?
C16 N5 C15 C28 169.3(3) . . . . ?
C16 N5 C15 C14 -9.2(5) . . . . ?
C15 N5 C16 C17 178.5(3) . . . . ?
N5 C16 C17 C22 -6.3(5) . . . . ?
N5 C16 C17 C18 172.7(3) . . . . ?
C22 C17 C18 C19 -0.4(5) . . . . ?
C16 C17 C18 C19 -179.5(3) . . . . ?
C17 C18 C19 C20 -1.6(5) . . . . ?
C25 N6 C20 C19 168.8(3) . . . . ?
C23 N6 C20 C19 -11.2(5) . . . . ?
C25 N6 C20 C21 -13.1(5) . . . . ?
C23 N6 C20 C21 166.9(3) . . . . ?
C18 C19 C20 N6 -179.3(3) . . . . ?
C18 C19 C20 C21 2.5(5) . . . . ?
N6 C20 C21 C22 -179.6(3) . . . . ?
C19 C20 C21 C22 -1.4(5) . . . . ?
C20 C21 C22 C17 -0.6(5) . . . . ?
C18 C17 C22 C21 1.5(5) . . . . ?
C16 C17 C22 C21 -179.4(3) . . . . ?
C20 N6 C23 C24 88.9(4) . . . . ?
C25 N6 C23 C24 -91.0(4) . . . . ?
C20 N6 C25 C26 90.9(4) . . . . ?
C23 N6 C25 C26 -89.1(4) . . . . ?
N5 C15 C28 N8 -178.7(3) . . . . ?
C14 C15 C28 N8 -0.1(5) . . . . ?
N5 C15 C28 C27 -0.9(5) . . . . ?
C14 C15 C28 C27 177.6(3) . . . . ?
C29 N8 C28 C15 173.7(3) . . . . ?
C29 N8 C28 C27 -4.0(5) . . . . ?
C28 N8 C29 C30 -178.1(3) . . . . ?
N8 C29 C30 C35 -0.7(6) . . . . ?
N8 C29 C30 C31 -178.2(4) . . . . ?
C35 C30 C31 C32 0.4(6) . . . . ?
C29 C30 C31 C32 178.1(4) . . . . ?
C30 C31 C32 C33 2.3(7) . . . . ?
C36 N9 C33 C32 12.6(7) . . . . ?
C38 N9 C33 C32 -155.5(4) . . . . ?
C36 N9 C33 C34 -164.7(4) . . . . ?
C38 N9 C33 C34 27.1(7) . . . . ?
C31 C32 C33 N9 179.5(5) . . . . ?
C31 C32 C33 C34 -3.0(7) . . . . ?
N9 C33 C34 C35 178.5(4) . . . . ?
C32 C33 C34 C35 1.1(6) . . . . ?
C33 C34 C35 C30 1.7(6) . . . . ?
C31 C30 C35 C34 -2.4(6) . . . . ?
C29 C30 C35 C34 -180.0(3) . . . . ?
C33 N9 C36 C37 -94.1(6) . . . . ?
C38 N9 C36 C37 74.2(6) . . . . ?
C33 N9 C38 C39 -99.0(5) . . . . ?
C36 N9 C38 C39 92.4(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"N, N'-bis [(4-diethylaminophenyl) methylidene] diaminomaleonitrile"
_chemical_name_common            DE2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and diethyl ether'
####################################################################### 
# 
# 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_DE2_293K
_database_code_depnum_ccdc_archive 'CCDC 1811067'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H30 N6'
_chemical_formula_moiety         'C26 H30 N6'
_chemical_formula_weight         426.56
_chemical_melting_point          551

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.1906(5)
_cell_length_b                   11.2290(6)
_cell_length_c                   18.1200(9)
_cell_angle_alpha                79.943(4)
_cell_angle_beta                 76.137(4)
_cell_angle_gamma                89.745(4)
_cell_volume                     1786.27(17)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    2259
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      26.40
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684.00
_exptl_absorpt_coefficient_mu    0.073
_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_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            11413
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_theta_max         24.794
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_full        24.794
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6050
_reflns_number_gt                2773
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1783
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.2478
_refine_ls_wR_factor_gt          0.1859
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6050
_refine_ls_number_parameters     433
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1029P)²+0.1549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.2302(5) 0.4875(4) 0.9105(2) 0.0870(13) Uani 1 1 d . . . . .
N2 N 0.1446(3) 0.4868(3) 0.91402(18) 0.0629(10) Uani 1 1 d . . . . .
N3 N 0.7176(4) 0.4175(4) 0.6454(2) 0.0878(13) Uani 1 1 d . U . . .
N4 N 0.0917(4) 0.2200(4) 0.5402(2) 0.0788(12) Uani 1 1 d . . . . .
N5 N 0.4514(3) 0.1501(3) 0.55740(17) 0.0516(9) Uani 1 1 d . . . . .
N6 N 1.0422(3) 0.1579(3) 0.28260(18) 0.0628(10) Uani 1 1 d . . . . .
N7 N 0.5050(5) 0.0839(4) 0.7459(2) 0.0940(15) Uani 1 1 d . . . . .
N8 N 0.1453(3) 0.1464(3) 0.72768(18) 0.0546(9) Uani 1 1 d . . . . .
N9 N -0.4232(4) 0.1805(5) 1.0074(2) 0.1145(18) Uani 1 1 d . U . . .
C1 C -0.1298(5) 0.4892(4) 0.9364(2) 0.0630(12) Uani 1 1 d . . . . .
C2 C 0.0052(5) 0.4922(4) 0.9627(2) 0.0609(12) Uani 1 1 d . . . . .
C3 C 0.1574(5) 0.4641(4) 0.8452(2) 0.0613(12) Uani 1 1 d . . . . .
H3 H 0.0711 0.4511 0.8290 0.074 Uiso 1 1 calc R U . . .
C4 C 0.3010(4) 0.4583(3) 0.7934(2) 0.0525(10) Uani 1 1 d . . . . .
C5 C 0.3114(4) 0.4264(3) 0.7206(2) 0.0578(11) Uani 1 1 d . . . . .
H5 H 0.2242 0.4123 0.7055 0.069 Uiso 1 1 calc R U . . .
C6 C 0.4479(4) 0.4160(4) 0.6718(2) 0.0588(11) Uani 1 1 d . . . . .
H6 H 0.4509 0.3952 0.6240 0.071 Uiso 1 1 calc R U . . .
C7 C 0.5818(4) 0.4352(4) 0.6912(2) 0.0593(11) Uani 1 1 d . . . . .
C8 C 0.5707(5) 0.4720(4) 0.7636(2) 0.0717(13) Uani 1 1 d . . . . .
H8 H 0.6574 0.4897 0.7781 0.086 Uiso 1 1 calc R U . . .
C9 C 0.4338(5) 0.4814(4) 0.8117(2) 0.0661(12) Uani 1 1 d . . . . .
H9 H 0.4301 0.5044 0.8590 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7303(5) 0.3728(5) 0.5739(3) 0.0790(15) Uani 1 1 d . . . . .
H10A H 0.6504 0.3123 0.5821 0.095 Uiso 1 1 calc R U . . .
H10B H 0.8245 0.3325 0.5626 0.095 Uiso 1 1 calc R U . . .
C11 C 0.7240(6) 0.4639(5) 0.5052(3) 0.1041(19) Uani 1 1 d . . . . .
H11A H 0.7334 0.4247 0.4613 0.125 Uiso 1 1 calc R U . . .
H11B H 0.6298 0.5030 0.5146 0.125 Uiso 1 1 calc R U . . .
H11C H 0.8045 0.5232 0.4950 0.125 Uiso 1 1 calc R U . . .
C12 C 0.8656(5) 0.4344(5) 0.6683(3) 0.0906(16) Uani 1 1 d . U . . .
H12A H 0.8533 0.4075 0.7233 0.109 Uiso 1 1 calc R U . . .
H12B H 0.9437 0.3889 0.6407 0.109 Uiso 1 1 calc R U . . .
C13 C 0.9010(7) 0.5571(5) 0.6480(3) 0.133(3) Uani 1 1 d . . . . .
H13A H 0.9933 0.5738 0.6610 0.159 Uiso 1 1 calc R U . . .
H13B H 0.9121 0.5822 0.5935 0.159 Uiso 1 1 calc R U . . .
H13C H 0.8222 0.6006 0.6756 0.159 Uiso 1 1 calc R U . . .
C14 C 0.1855(5) 0.1929(4) 0.5707(2) 0.0557(11) Uani 1 1 d . . . . .
C15 C 0.3105(4) 0.1582(3) 0.6034(2) 0.0490(10) Uani 1 1 d . . . . .
C16 C 0.4784(4) 0.1885(3) 0.4835(2) 0.0528(11) Uani 1 1 d . . . . .
H16 H 0.4014 0.2224 0.4626 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6225(4) 0.1806(3) 0.4328(2) 0.0461(10) Uani 1 1 d . . . . .
C18 C 0.6528(4) 0.2338(4) 0.3557(2) 0.0567(11) Uani 1 1 d . . . . .
H18 H 0.5772 0.2746 0.3369 0.068 Uiso 1 1 calc R U . . .
C19 C 0.7891(4) 0.2288(4) 0.3063(2) 0.0582(11) Uani 1 1 d . . . . .
H19 H 0.8052 0.2682 0.2552 0.070 Uiso 1 1 calc R U . . .
C20 C 0.9059(4) 0.1653(3) 0.3311(2) 0.0509(10) Uani 1 1 d . . . . .
C21 C 0.8761(4) 0.1111(3) 0.4103(2) 0.0540(10) Uani 1 1 d . . . . .
H21 H 0.9508 0.0698 0.4296 0.065 Uiso 1 1 calc R U . . .
C22 C 0.7383(4) 0.1193(3) 0.4584(2) 0.0521(10) Uani 1 1 d . . . . .
H22 H 0.7213 0.0827 0.5100 0.063 Uiso 1 1 calc R U . . .
C23 C 1.0839(5) 0.2333(4) 0.2059(2) 0.0672(13) Uani 1 1 d . . . . .
H23A H 1.1916 0.2492 0.1917 0.081 Uiso 1 1 calc R U . . .
H23B H 1.0364 0.3103 0.2080 0.081 Uiso 1 1 calc R U . . .
C24 C 1.0413(6) 0.1785(5) 0.1450(2) 0.0918(17) Uani 1 1 d . . . . .
H24A H 1.0719 0.2326 0.0963 0.110 Uiso 1 1 calc R U . . .
H24B H 1.0899 0.1031 0.1414 0.110 Uiso 1 1 calc R U . . .
H24C H 0.9345 0.1643 0.1577 0.110 Uiso 1 1 calc R U . . .
C25 C 1.1521(4) 0.0724(4) 0.3042(2) 0.0660(13) Uani 1 1 d . . . . .
H25A H 1.2094 0.0449 0.2584 0.079 Uiso 1 1 calc R U . . .
H25B H 1.0995 0.0023 0.3396 0.079 Uiso 1 1 calc R U . . .
C26 C 1.2584(5) 0.1275(4) 0.3420(3) 0.0790(14) Uani 1 1 d . . . . .
H26A H 1.3280 0.0684 0.3551 0.095 Uiso 1 1 calc R U . . .
H26B H 1.3122 0.1959 0.3069 0.095 Uiso 1 1 calc R U . . .
H26C H 1.2024 0.1533 0.3880 0.095 Uiso 1 1 calc R U . . .
C27 C 0.4129(5) 0.1067(4) 0.7139(2) 0.0674(13) Uani 1 1 d . . . . .
C28 C 0.2865(4) 0.1366(3) 0.6812(2) 0.0534(11) Uani 1 1 d . . . . .
C29 C 0.1255(4) 0.1357(4) 0.8017(2) 0.0621(12) Uani 1 1 d . . . . .
H29 H 0.2080 0.1188 0.8226 0.075 Uiso 1 1 calc R U . . .
C30 C -0.0137(4) 0.1484(4) 0.8525(2) 0.0572(11) Uani 1 1 d . . . . .
C31 C -0.0276(5) 0.1345(5) 0.9313(2) 0.0859(16) Uani 1 1 d . . . . .
H31 H 0.0574 0.1180 0.9500 0.103 Uiso 1 1 calc R U . . .
C32 C -0.1598(5) 0.1438(5) 0.9822(2) 0.0908(18) Uani 1 1 d . . . . .
H32 H -0.1636 0.1322 1.0348 0.109 Uiso 1 1 calc R U . . .
C33 C -0.2897(5) 0.1705(4) 0.9573(2) 0.0714(14) Uani 1 1 d . . . . .
C34 C -0.2781(5) 0.1833(4) 0.8774(2) 0.0675(13) Uani 1 1 d . . . . .
H34 H -0.3626 0.1999 0.8582 0.081 Uiso 1 1 calc R U . . .
C35 C -0.1441(4) 0.1715(4) 0.8283(2) 0.0592(11) Uani 1 1 d . . . . .
H35 H -0.1400 0.1793 0.7758 0.071 Uiso 1 1 calc R U . . .
C36 C -0.4467(6) 0.1348(6) 1.0936(3) 0.108(2) Uani 1 1 d . U . . .
H36A H -0.5481 0.1011 1.1149 0.130 Uiso 1 1 calc R U . . .
H36B H -0.3777 0.0713 1.1023 0.130 Uiso 1 1 calc R U . . .
C37 C -0.4224(7) 0.2306(6) 1.1309(4) 0.139(3) Uani 1 1 d . . . . .
H37A H -0.4375 0.2008 1.1853 0.166 Uiso 1 1 calc R U . . .
H37B H -0.3216 0.2631 1.1101 0.166 Uiso 1 1 calc R U . . .
H37C H -0.4916 0.2929 1.1227 0.166 Uiso 1 1 calc R U . . .
C38 C -0.5479(7) 0.2581(7) 0.9792(3) 0.123(2) Uani 1 1 d D U . . .
H38A H -0.6025 0.3013 1.0185 0.148 Uiso 1 1 calc R U . . .
H38B H -0.5067 0.3152 0.9321 0.148 Uiso 1 1 calc R U . . .
C39 C -0.6355(8) 0.1699(8) 0.9670(5) 0.212(5) Uani 1 1 d D . . . .
H39A H -0.7187 0.2057 0.9490 0.255 Uiso 1 1 calc R U . . .
H39B H -0.5775 0.1278 0.9288 0.255 Uiso 1 1 calc R U . . .
H39C H -0.6723 0.1139 1.0144 0.255 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.132(5) . ?
N2 C3 1.293(5) . ?
N2 C2 1.378(4) . ?
N3 C7 1.358(4) . ?
N3 C10 1.448(5) . ?
N3 C12 1.535(6) . ?
N4 C14 1.143(5) . ?
N5 C16 1.297(4) . ?
N5 C15 1.374(4) . ?
N6 C20 1.359(4) . ?
N6 C23 1.461(5) . ?
N6 C25 1.464(5) . ?
N7 C27 1.140(5) . ?
N8 C29 1.294(5) . ?
N8 C28 1.383(4) . ?
N9 C33 1.358(5) . ?
N9 C36 1.519(7) . ?
N9 C38 1.565(7) . ?
C1 C2 1.434(6) . ?
C2 C2 1.375(7) 2_567 ?
C3 C4 1.434(5) . ?
C3 H3 0.9300 . ?
C4 C9 1.376(6) . ?
C4 C5 1.407(5) . ?
C5 C6 1.369(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.424(5) . ?
C8 C9 1.364(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.481(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.382(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.436(6) . ?
C15 C28 1.353(5) . ?
C16 C17 1.431(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(5) . ?
C17 C22 1.392(5) . ?
C18 C19 1.362(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.405(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.419(5) . ?
C21 C22 1.368(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.482(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.510(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.438(6) . ?
C29 C30 1.408(5) . ?
C29 H29 0.9300 . ?
C30 C35 1.381(5) . ?
C30 C31 1.384(5) . ?
C31 C32 1.354(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.388(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.407(5) . ?
C34 C35 1.356(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.412(7) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.360(8) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 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
C3 N2 C2 120.6(4) . . ?
C7 N3 C10 121.4(4) . . ?
C7 N3 C12 122.8(3) . . ?
C10 N3 C12 115.7(3) . . ?
C16 N5 C15 120.1(3) . . ?
C20 N6 C23 121.2(4) . . ?
C20 N6 C25 121.6(3) . . ?
C23 N6 C25 117.2(3) . . ?
C29 N8 C28 120.4(4) . . ?
C33 N9 C36 121.3(4) . . ?
C33 N9 C38 120.1(4) . . ?
C36 N9 C38 118.0(4) . . ?
N1 C1 C2 175.2(4) . . ?
C2 C2 N2 119.4(5) 2_567 . ?
C2 C2 C1 118.7(4) 2_567 . ?
N2 C2 C1 121.8(3) . . ?
N2 C3 C4 121.8(4) . . ?
N2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C9 C4 C5 116.9(3) . . ?
C9 C4 C3 122.7(4) . . ?
C5 C4 C3 120.4(4) . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 122.3(4) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
N3 C7 C6 122.8(3) . . ?
N3 C7 C8 120.7(4) . . ?
C6 C7 C8 116.5(3) . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 122.9(4) . . ?
C8 C9 H9 118.6 . . ?
C4 C9 H9 118.6 . . ?
N3 C10 C11 116.4(4) . . ?
N3 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
N3 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N3 105.4(5) . . ?
C13 C12 H12A 110.7 . . ?
N3 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
N3 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C15 175.7(4) . . ?
C28 C15 N5 120.6(4) . . ?
C28 C15 C14 118.0(3) . . ?
N5 C15 C14 121.4(3) . . ?
N5 C16 C17 122.4(4) . . ?
N5 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C18 C17 C22 116.8(3) . . ?
C18 C17 C16 121.1(4) . . ?
C22 C17 C16 122.0(3) . . ?
C19 C18 C17 122.5(4) . . ?
C19 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
C18 C19 C20 121.1(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
N6 C20 C19 122.2(4) . . ?
N6 C20 C21 121.1(4) . . ?
C19 C20 C21 116.7(3) . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 122.3(4) . . ?
C21 C22 H22 118.8 . . ?
C17 C22 H22 118.8 . . ?
N6 C23 C24 113.9(4) . . ?
N6 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N6 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C25 C26 112.4(3) . . ?
N6 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
N6 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N7 C27 C28 174.1(4) . . ?
C15 C28 N8 120.7(4) . . ?
C15 C28 C27 118.0(3) . . ?
N8 C28 C27 121.2(3) . . ?
N8 C29 C30 123.8(4) . . ?
N8 C29 H29 118.1 . . ?
C30 C29 H29 118.1 . . ?
C35 C30 C31 115.8(3) . . ?
C35 C30 C29 123.3(4) . . ?
C31 C30 C29 120.9(4) . . ?
C32 C31 C30 122.9(4) . . ?
C32 C31 H31 118.6 . . ?
C30 C31 H31 118.6 . . ?
C31 C32 C33 121.0(4) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
N9 C33 C32 121.9(4) . . ?
N9 C33 C34 121.1(4) . . ?
C32 C33 C34 117.0(3) . . ?
C35 C34 C33 120.3(4) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C30 123.1(4) . . ?
C34 C35 H35 118.5 . . ?
C30 C35 H35 118.5 . . ?
C37 C36 N9 110.1(6) . . ?
C37 C36 H36A 109.6 . . ?
N9 C36 H36A 109.6 . . ?
C37 C36 H36B 109.6 . . ?
N9 C36 H36B 109.6 . . ?
H36A C36 H36B 108.2 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 N9 100.5(7) . . ?
C39 C38 H38A 111.7 . . ?
N9 C38 H38A 111.7 . . ?
C39 C38 H38B 111.7 . . ?
N9 C38 H38B 111.7 . . ?
H38A C38 H38B 109.4 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
C3 N2 C2 C2 175.3(5) . . . 2_567 ?
C3 N2 C2 C1 -8.4(6) . . . . ?
C2 N2 C3 C4 179.8(4) . . . . ?
N2 C3 C4 C9 -2.8(6) . . . . ?
N2 C3 C4 C5 176.3(4) . . . . ?
C9 C4 C5 C6 1.8(6) . . . . ?
C3 C4 C5 C6 -177.4(4) . . . . ?
C4 C5 C6 C7 0.3(6) . . . . ?
C10 N3 C7 C6 -2.2(7) . . . . ?
C12 N3 C7 C6 -177.7(5) . . . . ?
C10 N3 C7 C8 176.0(5) . . . . ?
C12 N3 C7 C8 0.5(7) . . . . ?
C5 C6 C7 N3 175.6(4) . . . . ?
C5 C6 C7 C8 -2.7(7) . . . . ?
N3 C7 C8 C9 -175.4(4) . . . . ?
C6 C7 C8 C9 3.0(7) . . . . ?
C7 C8 C9 C4 -1.0(7) . . . . ?
C5 C4 C9 C8 -1.4(7) . . . . ?
C3 C4 C9 C8 177.7(4) . . . . ?
C7 N3 C10 C11 83.7(6) . . . . ?
C12 N3 C10 C11 -100.5(5) . . . . ?
C7 N3 C12 C13 -83.0(6) . . . . ?
C10 N3 C12 C13 101.3(5) . . . . ?
C16 N5 C15 C28 -169.5(3) . . . . ?
C16 N5 C15 C14 8.7(5) . . . . ?
C15 N5 C16 C17 -179.0(3) . . . . ?
N5 C16 C17 C18 -172.9(4) . . . . ?
N5 C16 C17 C22 7.1(6) . . . . ?
C22 C17 C18 C19 -0.7(6) . . . . ?
C16 C17 C18 C19 179.4(4) . . . . ?
C17 C18 C19 C20 1.9(6) . . . . ?
C23 N6 C20 C19 11.2(6) . . . . ?
C25 N6 C20 C19 -167.4(4) . . . . ?
C23 N6 C20 C21 -167.2(4) . . . . ?
C25 N6 C20 C21 14.1(6) . . . . ?
C18 C19 C20 N6 179.2(4) . . . . ?
C18 C19 C20 C21 -2.3(6) . . . . ?
N6 C20 C21 C22 -180.0(4) . . . . ?
C19 C20 C21 C22 1.5(6) . . . . ?
C20 C21 C22 C17 -0.4(6) . . . . ?
C18 C17 C22 C21 -0.1(6) . . . . ?
C16 C17 C22 C21 179.9(3) . . . . ?
C20 N6 C23 C24 -88.8(5) . . . . ?
C25 N6 C23 C24 89.9(5) . . . . ?
C20 N6 C25 C26 -92.1(5) . . . . ?
C23 N6 C25 C26 89.2(4) . . . . ?
N5 C15 C28 N8 179.0(3) . . . . ?
C14 C15 C28 N8 0.7(5) . . . . ?
N5 C15 C28 C27 0.8(6) . . . . ?
C14 C15 C28 C27 -177.5(4) . . . . ?
C29 N8 C28 C15 -174.1(4) . . . . ?
C29 N8 C28 C27 4.1(6) . . . . ?
C28 N8 C29 C30 177.9(4) . . . . ?
N8 C29 C30 C35 1.2(7) . . . . ?
N8 C29 C30 C31 179.2(4) . . . . ?
C35 C30 C31 C32 -0.6(7) . . . . ?
C29 C30 C31 C32 -178.8(5) . . . . ?
C30 C31 C32 C33 -1.2(9) . . . . ?
C36 N9 C33 C32 -14.6(8) . . . . ?
C38 N9 C33 C32 155.5(5) . . . . ?
C36 N9 C33 C34 163.5(5) . . . . ?
C38 N9 C33 C34 -26.4(8) . . . . ?
C31 C32 C33 N9 -179.9(5) . . . . ?
C31 C32 C33 C34 2.0(8) . . . . ?
N9 C33 C34 C35 -179.2(5) . . . . ?
C32 C33 C34 C35 -1.0(7) . . . . ?
C33 C34 C35 C30 -0.9(7) . . . . ?
C31 C30 C35 C34 1.7(7) . . . . ?
C29 C30 C35 C34 179.8(4) . . . . ?
C33 N9 C36 C37 95.5(6) . . . . ?
C38 N9 C36 C37 -74.8(6) . . . . ?
C33 N9 C38 C39 98.8(7) . . . . ?
C36 N9 C38 C39 -90.8(6) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"N, N'-bis [(4-diethylaminophenyl) methylidene] diaminomaleonitrile"
_chemical_name_common            DE2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and diethyl ether'
####################################################################### 
# 
# 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_DE2_393K
_database_code_depnum_ccdc_archive 'CCDC 1811068'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H30 N6'
_chemical_formula_moiety         'C26 H30 N6'
_chemical_formula_weight         426.56
_chemical_melting_point          551

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.2864(7)
_cell_length_b                   11.4128(7)
_cell_length_c                   18.2356(12)
_cell_angle_alpha                80.141(6)
_cell_angle_beta                 76.139(6)
_cell_angle_gamma                89.451(6)
_cell_volume                     1847.7(2)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    1666
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      28.25
_cell_measurement_temperature    393
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684.00
_exptl_absorpt_coefficient_mu    0.071
_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_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.993

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      393
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            11805
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_theta_max         24.790
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_full        24.790
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6260
_reflns_number_gt                1912
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2562
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.2965
_refine_ls_wR_factor_gt          0.1952
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6260
_refine_ls_number_parameters     433
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1165P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.2277(6) 0.5105(6) 0.0900(3) 0.134(2) Uani 1 1 d . . . . .
N2 N 0.8545(4) 0.5123(4) 0.0852(2) 0.0936(14) Uani 1 1 d . . . . .
N3 N 0.2849(5) 0.5746(5) 0.3543(3) 0.136(2) Uani 1 1 d . U . . .
N4 N 0.9051(6) 0.7780(5) 0.4580(3) 0.1220(19) Uani 1 1 d . . . . .
N5 N 0.5497(4) 0.8486(3) 0.4411(2) 0.0841(13) Uani 1 1 d . . . . .
N6 N -0.0351(5) 0.8443(5) 0.7140(2) 0.1095(16) Uani 1 1 d . U . . .
N7 N 0.4961(6) 0.9152(6) 0.2541(3) 0.151(3) Uani 1 1 d . . . . .
N8 N 0.8525(4) 0.8506(3) 0.2721(2) 0.0877(13) Uani 1 1 d . . . . .
N9 N 1.4164(6) 0.8135(6) -0.0058(3) 0.161(2) Uani 1 1 d . U . . .
C1 C 1.1290(7) 0.5092(6) 0.0642(3) 0.0962(19) Uani 1 1 d . . . . .
C2 C 0.9951(6) 0.5078(5) 0.0378(3) 0.0898(16) Uani 1 1 d . . . . .
C3 C 0.8421(5) 0.5352(4) 0.1536(3) 0.0899(16) Uani 1 1 d . . . . .
H3 H 0.9275 0.5486 0.1695 0.108 Uiso 1 1 calc R U . . .
C4 C 0.7000(6) 0.5404(5) 0.2052(3) 0.0810(15) Uani 1 1 d . . . . .
C5 C 0.6880(5) 0.5724(5) 0.2773(3) 0.0965(17) Uani 1 1 d . . . . .
H5 H 0.7740 0.5888 0.2919 0.116 Uiso 1 1 calc R U . . .
C6 C 0.5536(6) 0.5801(5) 0.3266(3) 0.0955(17) Uani 1 1 d . . . . .
H6 H 0.5504 0.5997 0.3744 0.115 Uiso 1 1 calc R U . . .
C7 C 0.4225(6) 0.5595(5) 0.3074(3) 0.0914(16) Uani 1 1 d . . . . .
C8 C 0.4323(6) 0.5239(5) 0.2355(3) 0.107(2) Uani 1 1 d . . . . .
H8 H 0.3467 0.5053 0.2213 0.128 Uiso 1 1 calc R U . . .
C9 C 0.5679(6) 0.5174(5) 0.1875(3) 0.0908(17) Uani 1 1 d . . . . .
H9 H 0.5718 0.4961 0.1401 0.109 Uiso 1 1 calc R U . . .
C10 C 0.2720(7) 0.6246(6) 0.4244(4) 0.138(3) Uani 1 1 d . . . . .
H10A H 0.3530 0.6822 0.4159 0.165 Uiso 1 1 calc R U . . .
H10B H 0.1801 0.6667 0.4342 0.165 Uiso 1 1 calc R U . . .
C11 C 0.2743(9) 0.5379(8) 0.4914(4) 0.179(4) Uani 1 1 d . . . . .
H11A H 0.2654 0.5772 0.5347 0.215 Uiso 1 1 calc R U . . .
H11B H 0.1929 0.4816 0.5012 0.215 Uiso 1 1 calc R U . . .
H11C H 0.3661 0.4971 0.4829 0.215 Uiso 1 1 calc R U . . .
C12 C 0.1332(7) 0.5634(8) 0.3288(4) 0.153(3) Uani 1 1 d D U . . .
H12A H 0.0559 0.6093 0.3557 0.184 Uiso 1 1 calc R U . . .
H12B H 0.1466 0.5880 0.2739 0.184 Uiso 1 1 calc R U . . .
C13 C 0.1031(10) 0.4433(8) 0.3510(5) 0.222(5) Uani 1 1 d D . . . .
H13A H 0.0123 0.4233 0.3388 0.266 Uiso 1 1 calc R U . . .
H13B H 0.1828 0.4007 0.3243 0.266 Uiso 1 1 calc R U . . .
H13C H 0.0931 0.4218 0.4052 0.266 Uiso 1 1 calc R U . . .
C14 C 0.8146(7) 0.8061(5) 0.4278(3) 0.0906(18) Uani 1 1 d . . . . .
C15 C 0.6898(5) 0.8398(4) 0.3954(3) 0.0774(14) Uani 1 1 d . . . . .
C16 C 0.5238(5) 0.8143(4) 0.5143(3) 0.0858(16) Uani 1 1 d . . . . .
H16 H 0.6009 0.7830 0.5352 0.103 Uiso 1 1 calc R U . . .
C17 C 0.3815(5) 0.8223(5) 0.5649(3) 0.0782(14) Uani 1 1 d . . . . .
C18 C 0.3539(5) 0.7727(5) 0.6425(3) 0.0974(17) Uani 1 1 d . . . . .
H18 H 0.4296 0.7353 0.6620 0.117 Uiso 1 1 calc R U . . .
C19 C 0.2166(6) 0.7783(5) 0.6904(3) 0.0985(17) Uani 1 1 d . . . . .
H19 H 0.2007 0.7414 0.7414 0.118 Uiso 1 1 calc R U . . .
C20 C 0.0999(6) 0.8370(5) 0.6659(3) 0.0878(16) Uani 1 1 d . . . . .
C21 C 0.1284(5) 0.8882(4) 0.5872(3) 0.0895(16) Uani 1 1 d . . . . .
H21 H 0.0540 0.9280 0.5678 0.107 Uiso 1 1 calc R U . . .
C22 C 0.2655(5) 0.8792(4) 0.5395(3) 0.0854(16) Uani 1 1 d . . . . .
H22 H 0.2811 0.9128 0.4879 0.102 Uiso 1 1 calc R U . . .
C23 C -0.0757(6) 0.7710(6) 0.7915(3) 0.123(2) Uani 1 1 d . U . . .
H23A H -0.1818 0.7537 0.8053 0.147 Uiso 1 1 calc R U . . .
H23B H -0.0262 0.6959 0.7901 0.147 Uiso 1 1 calc R U . . .
C24 C -0.0384(8) 0.8252(7) 0.8494(4) 0.163(3) Uani 1 1 d . . . . .
H24A H -0.0678 0.7728 0.8979 0.196 Uiso 1 1 calc R U . . .
H24B H 0.0669 0.8408 0.8370 0.196 Uiso 1 1 calc R U . . .
H24C H -0.0889 0.8987 0.8523 0.196 Uiso 1 1 calc R U . . .
C25 C -0.1462(6) 0.9302(6) 0.6926(3) 0.121(2) Uani 1 1 d . U . . .
H25A H -0.2019 0.9588 0.7379 0.146 Uiso 1 1 calc R U . . .
H25B H -0.0954 0.9980 0.6563 0.146 Uiso 1 1 calc R U . . .
C26 C -0.2488(7) 0.8728(6) 0.6580(4) 0.144(3) Uani 1 1 d . U . . .
H26A H -0.3196 0.9291 0.6445 0.172 Uiso 1 1 calc R U . . .
H26B H -0.1936 0.8455 0.6128 0.172 Uiso 1 1 calc R U . . .
H26C H -0.3000 0.8063 0.6942 0.172 Uiso 1 1 calc R U . . .
C27 C 0.5882(8) 0.8907(6) 0.2848(4) 0.111(2) Uani 1 1 d . . . . .
C28 C 0.7125(6) 0.8607(5) 0.3172(3) 0.0853(16) Uani 1 1 d . . . . .
C29 C 0.8724(6) 0.8617(4) 0.1990(3) 0.0951(17) Uani 1 1 d . . . . .
H29 H 0.7904 0.8787 0.1785 0.114 Uiso 1 1 calc R U . . .
C30 C 1.0115(6) 0.8499(5) 0.1471(3) 0.0871(16) Uani 1 1 d . . . . .
C31 C 1.0239(6) 0.8612(6) 0.0689(3) 0.122(2) Uani 1 1 d . . . . .
H31 H 0.9393 0.8758 0.0503 0.146 Uiso 1 1 calc R U . . .
C32 C 1.1554(6) 0.8518(6) 0.0187(3) 0.132(3) Uani 1 1 d . . . . .
H32 H 1.1591 0.8623 -0.0334 0.158 Uiso 1 1 calc R U . . .
C33 C 1.2826(6) 0.8273(6) 0.0425(3) 0.111(2) Uani 1 1 d . . . . .
C34 C 1.2737(6) 0.8144(5) 0.1222(3) 0.1053(19) Uani 1 1 d . . . . .
H34 H 1.3579 0.7969 0.1407 0.126 Uiso 1 1 calc R U . . .
C35 C 1.1403(6) 0.8278(4) 0.1722(3) 0.0909(16) Uani 1 1 d . . . . .
H35 H 1.1364 0.8218 0.2242 0.109 Uiso 1 1 calc R U . . .
C36 C 1.4404(8) 0.8658(7) -0.0943(4) 0.162(3) Uani 1 1 d D U . . .
H36A H 1.3702 0.9271 -0.1028 0.195 Uiso 1 1 calc R U . . .
H36B H 1.5404 0.8986 -0.1162 0.195 Uiso 1 1 calc R U . . .
C37 C 1.4152(9) 0.7663(9) -0.1252(5) 0.240(5) Uani 1 1 d D U . . .
H37A H 1.4272 0.7888 -0.1795 0.288 Uiso 1 1 calc R U . . .
H37B H 1.4850 0.7067 -0.1152 0.288 Uiso 1 1 calc R U . . .
H37C H 1.3161 0.7350 -0.1020 0.288 Uiso 1 1 calc R U . . .
C38 C 1.5421(10) 0.7387(8) 0.0228(5) 0.177(3) Uani 1 1 d D U . . .
H38A H 1.5039 0.6854 0.0710 0.213 Uiso 1 1 calc R U . . .
H38B H 1.5965 0.6941 -0.0152 0.213 Uiso 1 1 calc R U . . .
C39 C 1.6256(10) 0.8322(11) 0.0310(6) 0.271(7) Uani 1 1 d D U . . .
H39A H 1.7104 0.8024 0.0488 0.325 Uiso 1 1 calc R U . . .
H39B H 1.6579 0.8842 -0.0175 0.325 Uiso 1 1 calc R U . . .
H39C H 1.5665 0.8755 0.0676 0.325 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.127(7) . ?
N2 C3 1.296(5) . ?
N2 C2 1.388(6) . ?
N3 C7 1.385(6) . ?
N3 C10 1.466(7) . ?
N3 C12 1.598(8) . ?
N4 C14 1.126(7) . ?
N5 C16 1.290(6) . ?
N5 C15 1.379(5) . ?
N6 C20 1.358(5) . ?
N6 C23 1.478(7) . ?
N6 C25 1.490(7) . ?
N7 C27 1.138(7) . ?
N8 C29 1.285(6) . ?
N8 C28 1.377(5) . ?
N9 C33 1.365(6) . ?
N9 C38 1.576(9) . ?
N9 C36 1.584(8) . ?
C1 C2 1.439(8) . ?
C2 C2 1.400(9) 2_765 ?
C3 C4 1.433(6) . ?
C3 H3 0.9300 . ?
C4 C9 1.379(6) . ?
C4 C5 1.402(6) . ?
C5 C6 1.364(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.420(6) . ?
C8 C9 1.360(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.438(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.373(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.443(7) . ?
C15 C28 1.369(6) . ?
C16 C17 1.431(6) . ?
C16 H16 0.9300 . ?
C17 C22 1.385(6) . ?
C17 C18 1.396(6) . ?
C18 C19 1.370(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.416(7) . ?
C21 C22 1.373(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.421(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.475(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.431(8) . ?
C29 C30 1.427(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.386(7) . ?
C30 C35 1.387(6) . ?
C31 C32 1.356(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.364(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.417(7) . ?
C34 C35 1.376(6) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.396(9) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.375(10) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 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
C3 N2 C2 119.1(5) . . ?
C7 N3 C10 120.9(5) . . ?
C7 N3 C12 122.9(5) . . ?
C10 N3 C12 115.2(4) . . ?
C16 N5 C15 120.2(5) . . ?
C20 N6 C23 121.3(5) . . ?
C20 N6 C25 121.6(5) . . ?
C23 N6 C25 117.0(4) . . ?
C29 N8 C28 119.8(5) . . ?
C33 N9 C38 121.9(6) . . ?
C33 N9 C36 118.7(6) . . ?
C38 N9 C36 119.3(5) . . ?
N1 C1 C2 175.1(6) . . ?
N2 C2 C2 117.8(7) . 2_765 ?
N2 C2 C1 123.1(4) . . ?
C2 C2 C1 118.9(6) 2_765 . ?
N2 C3 C4 121.6(5) . . ?
N2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C9 C4 C5 115.9(4) . . ?
C9 C4 C3 123.1(5) . . ?
C5 C4 C3 120.9(5) . . ?
C6 C5 C4 121.8(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 121.7(5) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 N3 122.6(5) . . ?
C6 C7 C8 117.4(4) . . ?
N3 C7 C8 119.9(5) . . ?
C9 C8 C7 119.5(5) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C4 123.7(4) . . ?
C8 C9 H9 118.2 . . ?
C4 C9 H9 118.2 . . ?
C11 C10 N3 114.4(6) . . ?
C11 C10 H10A 108.7 . . ?
N3 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
N3 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N3 100.3(8) . . ?
C13 C12 H12A 111.7 . . ?
N3 C12 H12A 111.7 . . ?
C13 C12 H12B 111.7 . . ?
N3 C12 H12B 111.7 . . ?
H12A C12 H12B 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C15 175.1(6) . . ?
C28 C15 N5 120.0(5) . . ?
C28 C15 C14 118.3(4) . . ?
N5 C15 C14 121.7(5) . . ?
N5 C16 C17 122.9(5) . . ?
N5 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C22 C17 C18 117.0(4) . . ?
C22 C17 C16 122.0(5) . . ?
C18 C17 C16 121.0(5) . . ?
C19 C18 C17 120.8(5) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 122.7(5) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
N6 C20 C19 122.4(5) . . ?
N6 C20 C21 121.1(5) . . ?
C19 C20 C21 116.4(4) . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 122.9(5) . . ?
C21 C22 H22 118.6 . . ?
C17 C22 H22 118.6 . . ?
C24 C23 N6 114.1(6) . . ?
C24 C23 H23A 108.7 . . ?
N6 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
N6 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 N6 110.4(5) . . ?
C26 C25 H25A 109.6 . . ?
N6 C25 H25A 109.6 . . ?
C26 C25 H25B 109.6 . . ?
N6 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N7 C27 C28 175.2(6) . . ?
C15 C28 N8 119.6(5) . . ?
C15 C28 C27 118.5(5) . . ?
N8 C28 C27 121.9(5) . . ?
N8 C29 C30 124.6(5) . . ?
N8 C29 H29 117.7 . . ?
C30 C29 H29 117.7 . . ?
C31 C30 C35 116.9(4) . . ?
C31 C30 C29 121.3(6) . . ?
C35 C30 C29 121.8(5) . . ?
C32 C31 C30 122.1(6) . . ?
C32 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
C31 C32 C33 121.8(5) . . ?
C31 C32 H32 119.1 . . ?
C33 C32 H32 119.1 . . ?
C32 C33 N9 123.7(5) . . ?
C32 C33 C34 117.6(5) . . ?
N9 C33 C34 118.7(6) . . ?
C35 C34 C33 119.9(5) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C30 121.6(5) . . ?
C34 C35 H35 119.2 . . ?
C30 C35 H35 119.2 . . ?
C37 C36 N9 102.8(7) . . ?
C37 C36 H36A 111.2 . . ?
N9 C36 H36A 111.2 . . ?
C37 C36 H36B 111.2 . . ?
N9 C36 H36B 111.2 . . ?
H36A C36 H36B 109.1 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 N9 97.7(9) . . ?
C39 C38 H38A 112.2 . . ?
N9 C38 H38A 112.2 . . ?
C39 C38 H38B 112.2 . . ?
N9 C38 H38B 112.2 . . ?
H38A C38 H38B 109.8 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
C3 N2 C2 C2 -175.1(6) . . . 2_765 ?
C3 N2 C2 C1 9.9(8) . . . . ?
C2 N2 C3 C4 -179.7(5) . . . . ?
N2 C3 C4 C9 2.5(8) . . . . ?
N2 C3 C4 C5 -176.1(5) . . . . ?
C9 C4 C5 C6 0.0(8) . . . . ?
C3 C4 C5 C6 178.7(5) . . . . ?
C4 C5 C6 C7 -1.5(9) . . . . ?
C5 C6 C7 N3 -175.5(5) . . . . ?
C5 C6 C7 C8 3.1(9) . . . . ?
C10 N3 C7 C6 5.8(10) . . . . ?
C12 N3 C7 C6 173.7(6) . . . . ?
C10 N3 C7 C8 -172.7(6) . . . . ?
C12 N3 C7 C8 -4.8(9) . . . . ?
C6 C7 C8 C9 -3.2(8) . . . . ?
N3 C7 C8 C9 175.4(5) . . . . ?
C7 C8 C9 C4 1.8(9) . . . . ?
C5 C4 C9 C8 -0.1(8) . . . . ?
C3 C4 C9 C8 -178.9(5) . . . . ?
C7 N3 C10 C11 -88.5(8) . . . . ?
C12 N3 C10 C11 102.7(8) . . . . ?
C7 N3 C12 C13 87.3(8) . . . . ?
C10 N3 C12 C13 -104.1(7) . . . . ?
C16 N5 C15 C28 171.1(5) . . . . ?
C16 N5 C15 C14 -7.5(7) . . . . ?
C15 N5 C16 C17 179.3(4) . . . . ?
N5 C16 C17 C22 -7.0(7) . . . . ?
N5 C16 C17 C18 173.1(5) . . . . ?
C22 C17 C18 C19 1.5(8) . . . . ?
C16 C17 C18 C19 -178.6(5) . . . . ?
C17 C18 C19 C20 -2.7(8) . . . . ?
C23 N6 C20 C19 -12.0(8) . . . . ?
C25 N6 C20 C19 165.1(5) . . . . ?
C23 N6 C20 C21 167.1(5) . . . . ?
C25 N6 C20 C21 -15.7(8) . . . . ?
C18 C19 C20 N6 -178.7(5) . . . . ?
C18 C19 C20 C21 2.1(8) . . . . ?
N6 C20 C21 C22 -179.6(5) . . . . ?
C19 C20 C21 C22 -0.4(7) . . . . ?
C20 C21 C22 C17 -0.7(8) . . . . ?
C18 C17 C22 C21 0.2(8) . . . . ?
C16 C17 C22 C21 -179.7(5) . . . . ?
C20 N6 C23 C24 89.6(7) . . . . ?
C25 N6 C23 C24 -87.7(7) . . . . ?
C20 N6 C25 C26 93.9(6) . . . . ?
C23 N6 C25 C26 -88.8(6) . . . . ?
N5 C15 C28 N8 -179.4(4) . . . . ?
C14 C15 C28 N8 -0.7(7) . . . . ?
N5 C15 C28 C27 -0.5(7) . . . . ?
C14 C15 C28 C27 178.2(5) . . . . ?
C29 N8 C28 C15 175.0(5) . . . . ?
C29 N8 C28 C27 -3.9(8) . . . . ?
C28 N8 C29 C30 -178.3(4) . . . . ?
N8 C29 C30 C31 178.9(5) . . . . ?
N8 C29 C30 C35 -1.7(8) . . . . ?
C35 C30 C31 C32 -0.3(9) . . . . ?
C29 C30 C31 C32 179.2(6) . . . . ?
C30 C31 C32 C33 1.8(11) . . . . ?
C31 C32 C33 N9 178.0(6) . . . . ?
C31 C32 C33 C34 -1.4(11) . . . . ?
C38 N9 C33 C32 -155.5(7) . . . . ?
C36 N9 C33 C32 19.6(10) . . . . ?
C38 N9 C33 C34 23.8(10) . . . . ?
C36 N9 C33 C34 -161.1(6) . . . . ?
C32 C33 C34 C35 -0.6(9) . . . . ?
N9 C33 C34 C35 -180.0(6) . . . . ?
C33 C34 C35 C30 2.2(9) . . . . ?
C31 C30 C35 C34 -1.7(8) . . . . ?
C29 C30 C35 C34 178.9(5) . . . . ?
C33 N9 C36 C37 -98.4(8) . . . . ?
C38 N9 C36 C37 76.9(8) . . . . ?
C33 N9 C38 C39 -99.4(9) . . . . ?
C36 N9 C38 C39 85.6(8) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"N, N'-bis [(4-diethylaminophenyl) methylidene] diaminomaleonitrile"
_chemical_name_common            DE2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and diethyl ether'
####################################################################### 
# 
# 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_DE2_193K
_database_code_depnum_ccdc_archive 'CCDC 1811070'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H30 N6'
_chemical_formula_moiety         'C26 H30 N6'
_chemical_formula_weight         426.56
_chemical_melting_point          551

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.1682(4)
_cell_length_b                   11.1406(4)
_cell_length_c                   18.1008(7)
_cell_angle_alpha                79.815(3)
_cell_angle_beta                 76.166(4)
_cell_angle_gamma                89.991(3)
_cell_volume                     1765.17(13)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    2590
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      30.10
_cell_measurement_temperature    193
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684.00
_exptl_absorpt_coefficient_mu    0.074
_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_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      193
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            11451
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6120
_reflns_number_gt                3508
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1991
_refine_ls_wR_factor_gt          0.1601
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6120
_refine_ls_number_parameters     433
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0830P)²+0.5744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.2339(4) 0.5141(3) 0.08909(17) 0.0611(9) Uani 1 1 d . . . . .
N2 N 0.8556(3) 0.5140(2) 0.08651(14) 0.0432(7) Uani 1 1 d . . . . .
N3 N 0.2802(3) 0.5886(3) 0.35461(16) 0.0531(8) Uani 1 1 d . U . . .
N4 N 0.9108(3) 0.7809(3) 0.46087(16) 0.0514(8) Uani 1 1 d . . . . .
N5 N 0.5484(3) 0.8500(2) 0.44360(13) 0.0344(6) Uani 1 1 d . . . . .
N6 N -0.0450(3) 0.8427(2) 0.71903(14) 0.0384(7) Uani 1 1 d . . . . .
N7 N 0.4938(4) 0.9162(3) 0.25415(17) 0.0614(9) Uani 1 1 d . . . . .
N8 N 0.8561(3) 0.8540(2) 0.27286(14) 0.0368(7) Uani 1 1 d . . . . .
N9 N 1.4274(3) 0.8220(4) -0.00898(17) 0.0818(12) Uani 1 1 d . U . . .
C1 C 1.1321(4) 0.5137(3) 0.06283(18) 0.0443(9) Uani 1 1 d . . . . .
C2 C 0.9945(4) 0.5082(3) 0.03716(17) 0.0418(8) Uani 1 1 d . . . . .
C3 C 0.8447(4) 0.5363(3) 0.15587(17) 0.0428(9) Uani 1 1 d . . . . .
H3 H 0.9334 0.5483 0.1726 0.051 Uiso 1 1 calc R U . . .
C4 C 0.6992(3) 0.5431(3) 0.20761(16) 0.0367(8) Uani 1 1 d . . . . .
C5 C 0.6890(3) 0.5738(3) 0.28059(17) 0.0385(8) Uani 1 1 d . . . . .
H5 H 0.7786 0.5874 0.2961 0.046 Uiso 1 1 calc R U . . .
C6 C 0.5522(3) 0.5844(3) 0.33000(17) 0.0388(8) Uani 1 1 d . . . . .
H6 H 0.5492 0.6035 0.3794 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4166(3) 0.5678(3) 0.30908(17) 0.0392(8) Uani 1 1 d . . . . .
C8 C 0.4282(4) 0.5313(3) 0.23671(17) 0.0450(9) Uani 1 1 d . . . . .
H8 H 0.3392 0.5140 0.2217 0.054 Uiso 1 1 calc R U . . .
C9 C 0.5650(4) 0.5206(3) 0.18830(17) 0.0432(9) Uani 1 1 d . . . . .
H9 H 0.5685 0.4971 0.1400 0.052 Uiso 1 1 calc R U . . .
C10 C 0.2690(4) 0.6306(3) 0.42770(19) 0.0501(10) Uani 1 1 d . . . . .
H10A H 0.1734 0.6725 0.4403 0.060 Uiso 1 1 calc R U . . .
H10B H 0.3520 0.6917 0.4203 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2746(4) 0.5329(4) 0.4962(2) 0.0629(11) Uani 1 1 d . . . . .
H11A H 0.2663 0.5702 0.5421 0.075 Uiso 1 1 calc R U . . .
H11B H 0.1910 0.4729 0.5056 0.075 Uiso 1 1 calc R U . . .
H11C H 0.3701 0.4921 0.4855 0.075 Uiso 1 1 calc R U . . .
C12 C 0.1356(4) 0.5672(3) 0.3335(2) 0.0536(9) Uani 1 1 d . U . . .
H12A H 0.0562 0.6140 0.3618 0.064 Uiso 1 1 calc R U . . .
H12B H 0.1478 0.5966 0.2774 0.064 Uiso 1 1 calc R U . . .
C13 C 0.0904(5) 0.4375(4) 0.3528(2) 0.0734(13) Uani 1 1 d . . . . .
H13A H -0.0044 0.4254 0.3386 0.088 Uiso 1 1 calc R U . . .
H13B H 0.1685 0.3914 0.3242 0.088 Uiso 1 1 calc R U . . .
H13C H 0.0769 0.4088 0.4085 0.088 Uiso 1 1 calc R U . . .
C14 C 0.8163(4) 0.8086(3) 0.43043(17) 0.0365(8) Uani 1 1 d . . . . .
C15 C 0.6902(3) 0.8428(3) 0.39737(16) 0.0333(7) Uani 1 1 d . . . . .
C16 C 0.5205(3) 0.8108(3) 0.51769(16) 0.0338(7) Uani 1 1 d . . . . .
H16 H 0.5989 0.7755 0.5392 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3757(3) 0.8188(3) 0.56841(16) 0.0324(7) Uani 1 1 d . . . . .
C18 C 0.3454(3) 0.7632(3) 0.64608(16) 0.0373(8) Uani 1 1 d . . . . .
H18 H 0.4220 0.7201 0.6653 0.045 Uiso 1 1 calc R U . . .
C19 C 0.2068(3) 0.7693(3) 0.69557(17) 0.0369(8) Uani 1 1 d . . . . .
H19 H 0.1888 0.7285 0.7479 0.044 Uiso 1 1 calc R U . . .
C20 C 0.0914(3) 0.8349(3) 0.66995(16) 0.0313(7) Uani 1 1 d . . . . .
C21 C 0.1217(3) 0.8905(3) 0.59103(16) 0.0347(7) Uani 1 1 d . . . . .
H21 H 0.0459 0.9343 0.5715 0.042 Uiso 1 1 calc R U . . .
C22 C 0.2597(3) 0.8815(3) 0.54245(16) 0.0337(7) Uani 1 1 d . . . . .
H22 H 0.2771 0.9191 0.4896 0.040 Uiso 1 1 calc R U . . .
C23 C -0.0890(4) 0.7657(3) 0.79564(17) 0.0423(8) Uani 1 1 d . . . . .
H23A H -0.0421 0.6859 0.7933 0.051 Uiso 1 1 calc R U . . .
H23B H -0.1994 0.7505 0.8097 0.051 Uiso 1 1 calc R U . . .
C24 C -0.0448(4) 0.8200(4) 0.85810(18) 0.0585(11) Uani 1 1 d . . . . .
H24A H -0.0776 0.7639 0.9077 0.070 Uiso 1 1 calc R U . . .
H24B H 0.0647 0.8335 0.8454 0.070 Uiso 1 1 calc R U . . .
H24C H -0.0928 0.8980 0.8618 0.070 Uiso 1 1 calc R U . . .
C25 C -0.1557(3) 0.9272(3) 0.69737(18) 0.0408(8) Uani 1 1 d . . . . .
H25A H -0.1022 1.0003 0.6619 0.049 Uiso 1 1 calc R U . . .
H25B H -0.2152 0.9541 0.7444 0.049 Uiso 1 1 calc R U . . .
C26 C -0.2617(4) 0.8728(3) 0.65857(19) 0.0472(9) Uani 1 1 d . . . . .
H26A H -0.3329 0.9339 0.6455 0.057 Uiso 1 1 calc R U . . .
H26B H -0.2040 0.8478 0.6112 0.057 Uiso 1 1 calc R U . . .
H26C H -0.3170 0.8016 0.6938 0.057 Uiso 1 1 calc R U . . .
C27 C 0.5875(4) 0.8952(3) 0.28542(18) 0.0434(9) Uani 1 1 d . . . . .
C28 C 0.7143(3) 0.8646(3) 0.31881(16) 0.0344(7) Uani 1 1 d . . . . .
C29 C 0.8749(4) 0.8653(3) 0.19871(17) 0.0439(9) Uani 1 1 d . . . . .
H29 H 0.7904 0.8831 0.1774 0.053 Uiso 1 1 calc R U . . .
C30 C 1.0167(4) 0.8522(3) 0.14735(17) 0.0398(8) Uani 1 1 d . . . . .
C31 C 1.0292(4) 0.8686(4) 0.06752(18) 0.0564(11) Uani 1 1 d . . . . .
H31 H 0.9419 0.8853 0.0486 0.068 Uiso 1 1 calc R U . . .
C32 C 1.1638(4) 0.8614(4) 0.01600(19) 0.0567(11) Uani 1 1 d . . . . .
H32 H 1.1690 0.8768 -0.0379 0.068 Uiso 1 1 calc R U . . .
C33 C 1.2935(4) 0.8316(4) 0.04155(18) 0.0512(10) Uani 1 1 d . . . . .
C34 C 1.2811(4) 0.8154(3) 0.12181(18) 0.0464(9) Uani 1 1 d . . . . .
H34 H 1.3674 0.7959 0.1412 0.056 Uiso 1 1 calc R U . . .
C35 C 1.1476(4) 0.8273(3) 0.17205(17) 0.0387(8) Uani 1 1 d . . . . .
H35 H 1.1438 0.8183 0.2257 0.046 Uiso 1 1 calc R U . . .
C36 C 1.4500(4) 0.8656(4) -0.0931(2) 0.0651(12) Uani 1 1 d . . . . .
H36A H 1.3809 0.9320 -0.1018 0.078 Uiso 1 1 calc R U . . .
H36B H 1.5542 0.9000 -0.1148 0.078 Uiso 1 1 calc R U . . .
C37 C 1.4241(5) 0.7698(4) -0.1344(2) 0.0771(14) Uani 1 1 d . . . . .
H37A H 1.4406 0.8038 -0.1896 0.092 Uiso 1 1 calc R U . . .
H37B H 1.4938 0.7046 -0.1271 0.092 Uiso 1 1 calc R U . . .
H37C H 1.3204 0.7366 -0.1141 0.092 Uiso 1 1 calc R U . . .
C38 C 1.5510(5) 0.7397(5) 0.0195(2) 0.0758(12) Uani 1 1 d . U . . .
H38A H 1.5061 0.6791 0.0666 0.091 Uiso 1 1 calc R U . . .
H38B H 1.6066 0.6968 -0.0213 0.091 Uiso 1 1 calc R U . . .
C39 C 1.6399(7) 0.8236(6) 0.0345(4) 0.156(3) Uani 1 1 d . . . . .
H39A H 1.7228 0.7833 0.0531 0.188 Uiso 1 1 calc R U . . .
H39B H 1.6807 0.8831 -0.0129 0.188 Uiso 1 1 calc R U . . .
H39C H 1.5811 0.8656 0.0743 0.188 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.145(4) . ?
N2 C3 1.303(4) . ?
N2 C2 1.379(4) . ?
N3 C7 1.368(4) . ?
N3 C10 1.461(4) . ?
N3 C12 1.494(5) . ?
N4 C14 1.148(4) . ?
N5 C16 1.297(4) . ?
N5 C15 1.378(3) . ?
N6 C20 1.363(3) . ?
N6 C25 1.459(4) . ?
N6 C23 1.461(4) . ?
N7 C27 1.139(4) . ?
N8 C29 1.295(4) . ?
N8 C28 1.383(3) . ?
N9 C33 1.361(4) . ?
N9 C36 1.479(5) . ?
N9 C38 1.582(5) . ?
C1 C2 1.449(5) . ?
C2 C2 1.370(6) 2_765 ?
C3 C4 1.446(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.391(4) . ?
C4 C5 1.404(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.419(4) . ?
C8 C9 1.366(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.509(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.461(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.446(5) . ?
C15 C28 1.363(4) . ?
C16 C17 1.435(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(4) . ?
C17 C22 1.401(4) . ?
C18 C19 1.378(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.409(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.414(4) . ?
C21 C22 1.372(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.507(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.511(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.448(5) . ?
C29 C30 1.431(4) . ?
C29 H29 0.9500 . ?
C30 C35 1.389(4) . ?
C30 C31 1.401(4) . ?
C31 C32 1.370(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.395(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.409(4) . ?
C34 C35 1.361(4) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.455(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.345(7) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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
C3 N2 C2 120.6(3) . . ?
C7 N3 C10 121.1(3) . . ?
C7 N3 C12 122.2(3) . . ?
C10 N3 C12 116.6(2) . . ?
C16 N5 C15 120.5(3) . . ?
C20 N6 C25 121.7(3) . . ?
C20 N6 C23 121.8(3) . . ?
C25 N6 C23 116.5(2) . . ?
C29 N8 C28 119.5(3) . . ?
C33 N9 C36 121.6(3) . . ?
C33 N9 C38 119.5(3) . . ?
C36 N9 C38 117.9(3) . . ?
N1 C1 C2 174.4(3) . . ?
C2 C2 N2 120.3(4) 2_765 . ?
C2 C2 C1 118.1(3) 2_765 . ?
N2 C2 C1 121.5(3) . . ?
N2 C3 C4 120.7(3) . . ?
N2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C9 C4 C5 117.2(3) . . ?
C9 C4 C3 122.7(3) . . ?
C5 C4 C3 120.1(3) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
N3 C7 C6 122.2(3) . . ?
N3 C7 C8 121.2(3) . . ?
C6 C7 C8 116.5(3) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C4 122.0(3) . . ?
C8 C9 H9 119.0 . . ?
C4 C9 H9 119.0 . . ?
N3 C10 C11 115.8(3) . . ?
N3 C10 H10A 108.3 . . ?
C11 C10 H10A 108.3 . . ?
N3 C10 H10B 108.3 . . ?
C11 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N3 110.7(3) . . ?
C13 C12 H12A 109.5 . . ?
N3 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C15 176.0(3) . . ?
C28 C15 N5 120.6(3) . . ?
C28 C15 C14 118.1(3) . . ?
N5 C15 C14 121.3(3) . . ?
N5 C16 C17 122.5(3) . . ?
N5 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C18 C17 C22 117.4(3) . . ?
C18 C17 C16 120.6(3) . . ?
C22 C17 C16 122.0(3) . . ?
C19 C18 C17 121.5(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 121.1(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
N6 C20 C19 121.3(3) . . ?
N6 C20 C21 121.3(3) . . ?
C19 C20 C21 117.4(2) . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 122.1(3) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
N6 C23 C24 113.8(3) . . ?
N6 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N6 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C25 C26 113.5(3) . . ?
N6 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
N6 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N7 C27 C28 174.7(3) . . ?
C15 C28 N8 120.2(3) . . ?
C15 C28 C27 118.3(3) . . ?
N8 C28 C27 121.4(3) . . ?
N8 C29 C30 123.1(3) . . ?
N8 C29 H29 118.5 . . ?
C30 C29 H29 118.5 . . ?
C35 C30 C31 116.8(3) . . ?
C35 C30 C29 123.3(3) . . ?
C31 C30 C29 119.9(3) . . ?
C32 C31 C30 121.9(3) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C31 C32 C33 120.9(3) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
N9 C33 C32 121.5(3) . . ?
N9 C33 C34 121.3(3) . . ?
C32 C33 C34 117.2(3) . . ?
C35 C34 C33 121.1(3) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C34 C35 C30 122.0(3) . . ?
C34 C35 H35 119.0 . . ?
C30 C35 H35 119.0 . . ?
C37 C36 N9 113.0(4) . . ?
C37 C36 H36A 109.0 . . ?
N9 C36 H36A 109.0 . . ?
C37 C36 H36B 109.0 . . ?
N9 C36 H36B 109.0 . . ?
H36A C36 H36B 107.8 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 N9 101.5(5) . . ?
C39 C38 H38A 111.5 . . ?
N9 C38 H38A 111.5 . . ?
C39 C38 H38B 111.5 . . ?
N9 C38 H38B 111.5 . . ?
H38A C38 H38B 109.3 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
C3 N2 C2 C2 -176.2(4) . . . 2_765 ?
C3 N2 C2 C1 6.6(5) . . . . ?
C2 N2 C3 C4 179.7(3) . . . . ?
N2 C3 C4 C9 3.2(5) . . . . ?
N2 C3 C4 C5 -176.5(3) . . . . ?
C9 C4 C5 C6 -1.8(5) . . . . ?
C3 C4 C5 C6 178.0(3) . . . . ?
C4 C5 C6 C7 -1.4(5) . . . . ?
C10 N3 C7 C6 0.5(5) . . . . ?
C12 N3 C7 C6 -178.1(3) . . . . ?
C10 N3 C7 C8 -177.7(3) . . . . ?
C12 N3 C7 C8 3.7(5) . . . . ?
C5 C6 C7 N3 -174.1(3) . . . . ?
C5 C6 C7 C8 4.2(5) . . . . ?
N3 C7 C8 C9 174.4(3) . . . . ?
C6 C7 C8 C9 -3.9(5) . . . . ?
C7 C8 C9 C4 0.9(5) . . . . ?
C5 C4 C9 C8 2.0(5) . . . . ?
C3 C4 C9 C8 -177.8(3) . . . . ?
C7 N3 C10 C11 -81.8(4) . . . . ?
C12 N3 C10 C11 96.9(4) . . . . ?
C7 N3 C12 C13 79.5(4) . . . . ?
C10 N3 C12 C13 -99.2(4) . . . . ?
C16 N5 C15 C28 169.0(3) . . . . ?
C16 N5 C15 C14 -9.1(4) . . . . ?
C15 N5 C16 C17 178.6(3) . . . . ?
N5 C16 C17 C18 172.6(3) . . . . ?
N5 C16 C17 C22 -7.2(4) . . . . ?
C22 C17 C18 C19 0.1(4) . . . . ?
C16 C17 C18 C19 -179.7(3) . . . . ?
C17 C18 C19 C20 -1.7(5) . . . . ?
C25 N6 C20 C19 169.0(3) . . . . ?
C23 N6 C20 C19 -11.9(4) . . . . ?
C25 N6 C20 C21 -12.3(4) . . . . ?
C23 N6 C20 C21 166.8(3) . . . . ?
C18 C19 C20 N6 -179.0(3) . . . . ?
C18 C19 C20 C21 2.2(4) . . . . ?
N6 C20 C21 C22 -179.9(3) . . . . ?
C19 C20 C21 C22 -1.1(4) . . . . ?
C20 C21 C22 C17 -0.5(5) . . . . ?
C18 C17 C22 C21 1.0(4) . . . . ?
C16 C17 C22 C21 -179.2(3) . . . . ?
C20 N6 C23 C24 89.1(4) . . . . ?
C25 N6 C23 C24 -91.7(3) . . . . ?
C20 N6 C25 C26 90.2(3) . . . . ?
C23 N6 C25 C26 -88.9(3) . . . . ?
N5 C15 C28 N8 -178.3(3) . . . . ?
C14 C15 C28 N8 -0.1(4) . . . . ?
N5 C15 C28 C27 -0.1(4) . . . . ?
C14 C15 C28 C27 178.1(3) . . . . ?
C29 N8 C28 C15 174.4(3) . . . . ?
C29 N8 C28 C27 -3.7(4) . . . . ?
C28 N8 C29 C30 -178.2(3) . . . . ?
N8 C29 C30 C35 -0.6(5) . . . . ?
N8 C29 C30 C31 -178.5(3) . . . . ?
C35 C30 C31 C32 -0.4(6) . . . . ?
C29 C30 C31 C32 177.6(4) . . . . ?
C30 C31 C32 C33 3.0(6) . . . . ?
C36 N9 C33 C32 12.2(6) . . . . ?
C38 N9 C33 C32 -155.4(4) . . . . ?
C36 N9 C33 C34 -165.9(4) . . . . ?
C38 N9 C33 C34 26.5(6) . . . . ?
C31 C32 C33 N9 178.8(4) . . . . ?
C31 C32 C33 C34 -3.0(6) . . . . ?
N9 C33 C34 C35 178.8(4) . . . . ?
C32 C33 C34 C35 0.6(6) . . . . ?
C33 C34 C35 C30 1.9(5) . . . . ?
C31 C30 C35 C34 -2.0(5) . . . . ?
C29 C30 C35 C34 -180.0(3) . . . . ?
C33 N9 C36 C37 -94.4(5) . . . . ?
C38 N9 C36 C37 73.4(5) . . . . ?
C33 N9 C38 C39 -98.0(5) . . . . ?
C36 N9 C38 C39 93.9(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"N, N'-bis [(4-diethylaminophenyl) methylidene] diaminomaleonitrile"
_chemical_name_common            DE2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and diethyl ether'
####################################################################### 
# 
# 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_DE2_343K
_database_code_depnum_ccdc_archive 'CCDC 1811071'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H30 N6'
_chemical_formula_moiety         'C26 H30 N6'
_chemical_formula_weight         426.56
_chemical_melting_point          551

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.2410(5)
_cell_length_b                   11.3265(6)
_cell_length_c                   18.1906(10)
_cell_angle_alpha                80.038(5)
_cell_angle_beta                 76.141(5)
_cell_angle_gamma                89.607(5)
_cell_volume                     1819.49(18)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    1949
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      20.73
_cell_measurement_temperature    343
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684.00
_exptl_absorpt_coefficient_mu    0.072
_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_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.993

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      343
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            11703
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_theta_max         24.790
_diffrn_reflns_theta_min         2.272
_diffrn_reflns_theta_full        24.790
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6186
_reflns_number_gt                2404
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2086
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2665
_refine_ls_wR_factor_gt          0.1908
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6186
_refine_ls_number_parameters     433
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1059P)²+0.0528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.2289(5) 0.4885(5) 0.9103(3) 0.1104(17) Uani 1 1 d . . . . .
N2 N 0.1449(4) 0.4877(3) 0.91422(19) 0.0745(11) Uani 1 1 d . . . . .
N3 N 0.7165(4) 0.4212(4) 0.6456(2) 0.1102(16) Uani 1 1 d . U . . .
N4 N 0.0940(5) 0.2212(4) 0.5404(2) 0.0970(15) Uani 1 1 d . . . . .
N5 N 0.4508(3) 0.1510(3) 0.55784(19) 0.0656(10) Uani 1 1 d . . . . .
N6 N 1.0387(4) 0.1571(4) 0.2838(2) 0.0850(13) Uani 1 1 d . . . . .
N7 N 0.5045(6) 0.0836(5) 0.7458(3) 0.126(2) Uani 1 1 d . . . . .
N8 N 0.1466(4) 0.1478(3) 0.7274(2) 0.0699(10) Uani 1 1 d . . . . .
N9 N -0.4218(5) 0.1845(6) 1.0062(3) 0.139(2) Uani 1 1 d . U . . .
C1 C -0.1283(6) 0.4907(5) 0.9361(3) 0.0778(15) Uani 1 1 d . . . . .
C2 C 0.0062(5) 0.4927(4) 0.9630(2) 0.0732(13) Uani 1 1 d . . . . .
C3 C 0.1572(5) 0.4646(4) 0.8460(2) 0.0751(13) Uani 1 1 d . . . . .
H3 H 0.0710 0.4512 0.8302 0.090 Uiso 1 1 calc R U . . .
C4 C 0.2998(5) 0.4590(4) 0.7934(2) 0.0664(12) Uani 1 1 d . . . . .
C5 C 0.3119(5) 0.4270(4) 0.7217(2) 0.0742(13) Uani 1 1 d . . . . .
H5 H 0.2254 0.4116 0.7068 0.089 Uiso 1 1 calc R U . . .
C6 C 0.4478(5) 0.4175(4) 0.6725(2) 0.0728(13) Uani 1 1 d . . . . .
H6 H 0.4510 0.3974 0.6247 0.087 Uiso 1 1 calc R U . . .
C7 C 0.5803(5) 0.4371(4) 0.6921(2) 0.0737(13) Uani 1 1 d . . . . .
C8 C 0.5701(5) 0.4739(4) 0.7627(2) 0.0864(15) Uani 1 1 d . . . . .
H8 H 0.6568 0.4929 0.7764 0.104 Uiso 1 1 calc R U . . .
C9 C 0.4334(5) 0.4826(4) 0.8122(2) 0.0802(14) Uani 1 1 d . . . . .
H9 H 0.4301 0.5047 0.8595 0.096 Uiso 1 1 calc R U . . .
C10 C 0.7290(5) 0.3749(5) 0.5737(3) 0.106(2) Uani 1 1 d . . . . .
H10A H 0.8222 0.3341 0.5627 0.127 Uiso 1 1 calc R U . . .
H10B H 0.6488 0.3156 0.5820 0.127 Uiso 1 1 calc R U . . .
C11 C 0.7236(7) 0.4646(6) 0.5057(3) 0.136(2) Uani 1 1 d . . . . .
H11A H 0.7326 0.4255 0.4620 0.164 Uiso 1 1 calc R U . . .
H11B H 0.6304 0.5041 0.5149 0.164 Uiso 1 1 calc R U . . .
H11C H 0.8043 0.5226 0.4956 0.164 Uiso 1 1 calc R U . . .
C12 C 0.8675(6) 0.4363(6) 0.6696(3) 0.1132(19) Uani 1 1 d . U . . .
H12A H 0.8550 0.4111 0.7246 0.136 Uiso 1 1 calc R U . . .
H12B H 0.9454 0.3907 0.6425 0.136 Uiso 1 1 calc R U . . .
C13 C 0.8988(9) 0.5555(6) 0.6484(4) 0.182(4) Uani 1 1 d . . . . .
H13A H 0.9903 0.5745 0.6607 0.219 Uiso 1 1 calc R U . . .
H13B H 0.9090 0.5782 0.5940 0.219 Uiso 1 1 calc R U . . .
H13C H 0.8193 0.5984 0.6753 0.219 Uiso 1 1 calc R U . . .
C14 C 0.1847(6) 0.1932(4) 0.5711(3) 0.0714(14) Uani 1 1 d . . . . .
C15 C 0.3099(5) 0.1592(4) 0.6042(2) 0.0637(12) Uani 1 1 d . . . . .
C16 C 0.4775(5) 0.1874(4) 0.4846(2) 0.0697(13) Uani 1 1 d . . . . .
H16 H 0.4007 0.2201 0.4636 0.084 Uiso 1 1 calc R U . . .
C17 C 0.6218(4) 0.1793(4) 0.4341(2) 0.0609(11) Uani 1 1 d . . . . .
C18 C 0.6506(5) 0.2317(4) 0.3564(2) 0.0747(13) Uani 1 1 d . . . . .
H18 H 0.5750 0.2715 0.3376 0.090 Uiso 1 1 calc R U . . .
C19 C 0.7870(5) 0.2261(4) 0.3072(2) 0.0733(13) Uani 1 1 d . . . . .
H19 H 0.8030 0.2642 0.2563 0.088 Uiso 1 1 calc R U . . .
C20 C 0.9018(5) 0.1648(4) 0.3320(2) 0.0631(12) Uani 1 1 d . . . . .
C21 C 0.8747(5) 0.1115(4) 0.4106(2) 0.0715(13) Uani 1 1 d . . . . .
H21 H 0.9499 0.0708 0.4293 0.086 Uiso 1 1 calc R U . . .
C22 C 0.7378(5) 0.1195(4) 0.4596(2) 0.0677(12) Uani 1 1 d . . . . .
H22 H 0.7221 0.0843 0.5111 0.081 Uiso 1 1 calc R U . . .
C23 C 1.0801(5) 0.2323(5) 0.2066(3) 0.0889(16) Uani 1 1 d . . . . .
H23A H 1.0317 0.3084 0.2085 0.107 Uiso 1 1 calc R U . . .
H23B H 1.1870 0.2488 0.1926 0.107 Uiso 1 1 calc R U . . .
C24 C 1.0390(6) 0.1768(5) 0.1465(3) 0.119(2) Uani 1 1 d . . . . .
H24A H 1.0689 0.2300 0.0979 0.143 Uiso 1 1 calc R U . . .
H24B H 1.0885 0.1024 0.1433 0.143 Uiso 1 1 calc R U . . .
H24C H 0.9330 0.1620 0.1592 0.143 Uiso 1 1 calc R U . . .
C25 C 1.1494(5) 0.0713(5) 0.3053(3) 0.0894(16) Uani 1 1 d . . . . .
H25A H 1.2065 0.0440 0.2596 0.107 Uiso 1 1 calc R U . . .
H25B H 1.0977 0.0019 0.3406 0.107 Uiso 1 1 calc R U . . .
C26 C 1.2524(6) 0.1265(5) 0.3419(3) 0.1079(19) Uani 1 1 d . . . . .
H26A H 1.3226 0.0687 0.3551 0.129 Uiso 1 1 calc R U . . .
H26B H 1.3049 0.1943 0.3067 0.129 Uiso 1 1 calc R U . . .
H26C H 1.1963 0.1523 0.3877 0.129 Uiso 1 1 calc R U . . .
C27 C 0.4121(6) 0.1071(5) 0.7146(3) 0.0877(17) Uani 1 1 d . . . . .
C28 C 0.2865(5) 0.1365(4) 0.6817(3) 0.0695(13) Uani 1 1 d . . . . .
C29 C 0.1274(5) 0.1369(4) 0.8011(2) 0.0762(14) Uani 1 1 d . . . . .
H29 H 0.2096 0.1199 0.8218 0.091 Uiso 1 1 calc R U . . .
C30 C -0.0122(5) 0.1495(4) 0.8522(2) 0.0686(12) Uani 1 1 d . . . . .
C31 C -0.0251(5) 0.1366(5) 0.9309(2) 0.1002(18) Uani 1 1 d . . . . .
H31 H 0.0597 0.1210 0.9496 0.120 Uiso 1 1 calc R U . . .
C32 C -0.1586(6) 0.1463(6) 0.9818(3) 0.117(2) Uani 1 1 d . . . . .
H32 H -0.1628 0.1354 1.0342 0.140 Uiso 1 1 calc R U . . .
C33 C -0.2869(5) 0.1718(5) 0.9569(2) 0.0876(16) Uani 1 1 d . . . . .
C34 C -0.2757(5) 0.1848(4) 0.8768(2) 0.0851(15) Uani 1 1 d . . . . .
H34 H -0.3596 0.2020 0.8577 0.102 Uiso 1 1 calc R U . . .
C35 C -0.1414(5) 0.1721(4) 0.8279(2) 0.0716(13) Uani 1 1 d . . . . .
H35 H -0.1371 0.1790 0.7757 0.086 Uiso 1 1 calc R U . . .
C36 C -0.4450(7) 0.1355(6) 1.0941(3) 0.135(2) Uani 1 1 d . U . . .
H36A H -0.5456 0.1023 1.1161 0.162 Uiso 1 1 calc R U . . .
H36B H -0.3752 0.0732 1.1027 0.162 Uiso 1 1 calc R U . . .
C37 C -0.4200(8) 0.2326(7) 1.1275(4) 0.189(4) Uani 1 1 d . U . . .
H37A H -0.4330 0.2068 1.1819 0.227 Uiso 1 1 calc R U . . .
H37B H -0.3201 0.2645 1.1052 0.227 Uiso 1 1 calc R U . . .
H37C H -0.4896 0.2934 1.1185 0.227 Uiso 1 1 calc R U . . .
C38 C -0.5479(9) 0.2591(7) 0.9777(4) 0.150(3) Uani 1 1 d D U . . .
H38A H -0.6028 0.3032 1.0160 0.180 Uiso 1 1 calc R U . . .
H38B H -0.5091 0.3138 0.9297 0.180 Uiso 1 1 calc R U . . .
C39 C -0.6312(9) 0.1676(9) 0.9685(5) 0.234(6) Uani 1 1 d D . . . .
H39A H -0.7159 0.1990 0.9506 0.281 Uiso 1 1 calc R U . . .
H39B H -0.5722 0.1247 0.9314 0.281 Uiso 1 1 calc R U . . .
H39C H -0.6648 0.1143 1.0168 0.281 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.140(6) . ?
N2 C3 1.291(5) . ?
N2 C2 1.380(5) . ?
N3 C7 1.368(5) . ?
N3 C10 1.470(6) . ?
N3 C12 1.578(7) . ?
N4 C14 1.128(6) . ?
N5 C16 1.288(5) . ?
N5 C15 1.383(5) . ?
N6 C20 1.367(4) . ?
N6 C23 1.477(6) . ?
N6 C25 1.480(6) . ?
N7 C27 1.139(6) . ?
N8 C29 1.293(5) . ?
N8 C28 1.379(5) . ?
N9 C33 1.373(5) . ?
N9 C36 1.563(7) . ?
N9 C38 1.570(8) . ?
C1 C2 1.441(7) . ?
C2 C2 1.363(8) 2_567 ?
C3 C4 1.439(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(5) . ?
C4 C9 1.397(6) . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.400(5) . ?
C8 C9 1.379(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.470(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.352(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.449(7) . ?
C15 C28 1.351(6) . ?
C16 C17 1.439(5) . ?
C16 H16 0.9300 . ?
C17 C22 1.394(5) . ?
C17 C18 1.397(6) . ?
C18 C19 1.368(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.416(5) . ?
C21 C22 1.375(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.475(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.482(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.441(7) . ?
C29 C30 1.420(5) . ?
C29 H29 0.9300 . ?
C30 C35 1.378(6) . ?
C30 C31 1.389(6) . ?
C31 C32 1.371(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.379(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.417(6) . ?
C34 C35 1.366(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.390(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.352(9) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 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
C3 N2 C2 120.5(4) . . ?
C7 N3 C10 121.2(4) . . ?
C7 N3 C12 122.7(4) . . ?
C10 N3 C12 115.7(3) . . ?
C16 N5 C15 120.6(4) . . ?
C20 N6 C23 120.8(4) . . ?
C20 N6 C25 122.0(4) . . ?
C23 N6 C25 117.1(3) . . ?
C29 N8 C28 120.0(4) . . ?
C33 N9 C36 119.5(5) . . ?
C33 N9 C38 121.4(5) . . ?
C36 N9 C38 118.8(4) . . ?
N1 C1 C2 175.6(5) . . ?
C2 C2 N2 120.3(6) 2_567 . ?
C2 C2 C1 118.2(5) 2_567 . ?
N2 C2 C1 121.4(4) . . ?
N2 C3 C4 122.1(5) . . ?
N2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C9 116.5(4) . . ?
C5 C4 C3 121.6(4) . . ?
C9 C4 C3 121.9(4) . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 121.8(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
N3 C7 C6 122.4(4) . . ?
N3 C7 C8 120.5(5) . . ?
C6 C7 C8 117.1(4) . . ?
C9 C8 C7 120.9(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C4 121.9(4) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
C11 C10 N3 116.0(5) . . ?
C11 C10 H10A 108.3 . . ?
N3 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
N3 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N3 102.7(6) . . ?
C13 C12 H12A 111.2 . . ?
N3 C12 H12A 111.2 . . ?
C13 C12 H12B 111.2 . . ?
N3 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C15 175.2(5) . . ?
C28 C15 N5 120.6(4) . . ?
C28 C15 C14 118.5(4) . . ?
N5 C15 C14 120.9(4) . . ?
N5 C16 C17 122.5(4) . . ?
N5 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C22 C17 C18 117.2(3) . . ?
C22 C17 C16 122.2(4) . . ?
C18 C17 C16 120.6(4) . . ?
C19 C18 C17 121.8(4) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 121.3(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
N6 C20 C19 122.3(4) . . ?
N6 C20 C21 120.0(4) . . ?
C19 C20 C21 117.7(4) . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 121.7(4) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
C24 C23 N6 113.6(4) . . ?
C24 C23 H23A 108.9 . . ?
N6 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
N6 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C25 C26 111.5(4) . . ?
N6 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
N6 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N7 C27 C28 175.0(5) . . ?
C15 C28 N8 120.2(4) . . ?
C15 C28 C27 118.5(4) . . ?
N8 C28 C27 121.2(4) . . ?
N8 C29 C30 123.7(4) . . ?
N8 C29 H29 118.2 . . ?
C30 C29 H29 118.2 . . ?
C35 C30 C31 116.4(4) . . ?
C35 C30 C29 122.9(4) . . ?
C31 C30 C29 120.7(4) . . ?
C32 C31 C30 122.1(5) . . ?
C32 C31 H31 118.9 . . ?
C30 C31 H31 118.9 . . ?
C31 C32 C33 121.2(5) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
N9 C33 C32 122.7(4) . . ?
N9 C33 C34 120.0(5) . . ?
C32 C33 C34 117.3(4) . . ?
C35 C34 C33 119.9(4) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C30 123.0(4) . . ?
C34 C35 H35 118.5 . . ?
C30 C35 H35 118.5 . . ?
C37 C36 N9 106.4(6) . . ?
C37 C36 H36A 110.5 . . ?
N9 C36 H36A 110.5 . . ?
C37 C36 H36B 110.5 . . ?
N9 C36 H36B 110.5 . . ?
H36A C36 H36B 108.6 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 N9 98.8(7) . . ?
C39 C38 H38A 112.0 . . ?
N9 C38 H38A 112.0 . . ?
C39 C38 H38B 112.0 . . ?
N9 C38 H38B 112.0 . . ?
H38A C38 H38B 109.7 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
C3 N2 C2 C2 174.6(5) . . . 2_567 ?
C3 N2 C2 C1 -9.5(7) . . . . ?
C2 N2 C3 C4 179.8(4) . . . . ?
N2 C3 C4 C5 176.0(4) . . . . ?
N2 C3 C4 C9 -2.4(7) . . . . ?
C9 C4 C5 C6 0.8(7) . . . . ?
C3 C4 C5 C6 -177.7(4) . . . . ?
C4 C5 C6 C7 1.3(7) . . . . ?
C10 N3 C7 C6 -3.8(8) . . . . ?
C12 N3 C7 C6 -176.5(5) . . . . ?
C10 N3 C7 C8 175.9(5) . . . . ?
C12 N3 C7 C8 3.2(8) . . . . ?
C5 C6 C7 N3 176.1(4) . . . . ?
C5 C6 C7 C8 -3.7(7) . . . . ?
N3 C7 C8 C9 -175.7(5) . . . . ?
C6 C7 C8 C9 4.1(7) . . . . ?
C7 C8 C9 C4 -2.1(7) . . . . ?
C5 C4 C9 C8 -0.4(7) . . . . ?
C3 C4 C9 C8 178.1(4) . . . . ?
C7 N3 C10 C11 85.6(7) . . . . ?
C12 N3 C10 C11 -101.2(6) . . . . ?
C7 N3 C12 C13 -85.4(6) . . . . ?
C10 N3 C12 C13 101.6(6) . . . . ?
C16 N5 C15 C28 -171.0(4) . . . . ?
C16 N5 C15 C14 8.4(6) . . . . ?
C15 N5 C16 C17 -179.2(4) . . . . ?
N5 C16 C17 C22 7.3(6) . . . . ?
N5 C16 C17 C18 -172.8(4) . . . . ?
C22 C17 C18 C19 -0.6(6) . . . . ?
C16 C17 C18 C19 179.5(4) . . . . ?
C17 C18 C19 C20 2.0(7) . . . . ?
C23 N6 C20 C19 11.4(7) . . . . ?
C25 N6 C20 C19 -166.6(4) . . . . ?
C23 N6 C20 C21 -167.0(4) . . . . ?
C25 N6 C20 C21 15.0(6) . . . . ?
C18 C19 C20 N6 179.5(4) . . . . ?
C18 C19 C20 C21 -2.1(6) . . . . ?
N6 C20 C21 C22 179.5(4) . . . . ?
C19 C20 C21 C22 1.0(6) . . . . ?
C20 C21 C22 C17 0.3(7) . . . . ?
C18 C17 C22 C21 -0.5(6) . . . . ?
C16 C17 C22 C21 179.4(4) . . . . ?
C20 N6 C23 C24 -89.1(5) . . . . ?
C25 N6 C23 C24 89.0(5) . . . . ?
C20 N6 C25 C26 -92.6(5) . . . . ?
C23 N6 C25 C26 89.3(5) . . . . ?
N5 C15 C28 N8 178.4(4) . . . . ?
C14 C15 C28 N8 -1.1(6) . . . . ?
N5 C15 C28 C27 1.7(6) . . . . ?
C14 C15 C28 C27 -177.7(4) . . . . ?
C29 N8 C28 C15 -173.6(4) . . . . ?
C29 N8 C28 C27 2.9(7) . . . . ?
C28 N8 C29 C30 178.7(4) . . . . ?
N8 C29 C30 C35 1.4(7) . . . . ?
N8 C29 C30 C31 180.0(5) . . . . ?
C35 C30 C31 C32 -0.2(8) . . . . ?
C29 C30 C31 C32 -178.9(5) . . . . ?
C30 C31 C32 C33 -1.4(9) . . . . ?
C36 N9 C33 C32 -17.1(9) . . . . ?
C38 N9 C33 C32 156.3(6) . . . . ?
C36 N9 C33 C34 162.8(5) . . . . ?
C38 N9 C33 C34 -23.8(9) . . . . ?
C31 C32 C33 N9 -178.6(5) . . . . ?
C31 C32 C33 C34 1.5(9) . . . . ?
N9 C33 C34 C35 -179.9(5) . . . . ?
C32 C33 C34 C35 0.0(8) . . . . ?
C33 C34 C35 C30 -1.6(7) . . . . ?
C31 C30 C35 C34 1.7(7) . . . . ?
C29 C30 C35 C34 -179.7(4) . . . . ?
C33 N9 C36 C37 97.0(7) . . . . ?
C38 N9 C36 C37 -76.6(7) . . . . ?
C33 N9 C38 C39 98.8(7) . . . . ?
C36 N9 C38 C39 -87.7(7) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"N, N'-bis [(4-diethylaminophenyl) methylidene] diaminomaleonitrile"
_chemical_name_common            DE2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and diethyl ether'
####################################################################### 
# 
# 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_DE2-HT
_database_code_depnum_ccdc_archive 'CCDC 1811081'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H30 N6'
_chemical_formula_moiety         'C26 H30 N6'
_chemical_formula_weight         426.56
_chemical_melting_point          551

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.2349(9)
_cell_length_b                   9.5192(15)
_cell_length_c                   9.8308(18)
_cell_angle_alpha                87.588(14)
_cell_angle_beta                 84.227(12)
_cell_angle_gamma                70.714(13)
_cell_volume                     635.79(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2387
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      21.04
_cell_measurement_temperature    443
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.077
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228.00
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  0.995

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      443
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            10243
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2358
_reflns_number_gt                1016
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.3135
_refine_ls_wR_factor_gt          0.2415
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2358
_refine_ls_number_parameters     182
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1885P)²+0.0079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.016
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.12
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.8214(3) 0.4389(2) 0.4225(2) 0.1421(9) Uani 1 1 d . . . . .
N2 N 0.8405(5) 0.7926(4) 0.3613(4) 0.2168(15) Uani 1 1 d . . . . .
N3 N 0.2599(6) 0.1448(4) 0.1609(4) 0.2256(16) Uani 1 1 d . . . . .
C1 C 0.8845(5) 0.6769(5) 0.4073(3) 0.1652(11) Uani 1 1 d . . . . .
C2 C 0.9276(4) 0.5259(3) 0.4585(2) 0.1383(9) Uani 1 1 d . . . . .
C3 C 0.6854(4) 0.4884(3) 0.3430(3) 0.1457(10) Uani 1 1 d . . . . .
H3 H 0.6565 0.5860 0.3113 0.175 Uiso 1 1 calc R U . . .
C4 C 0.5738(4) 0.4002(3) 0.2998(3) 0.1388(9) Uani 1 1 d . . . . .
C5 C 0.4380(5) 0.4549(3) 0.2062(4) 0.1771(12) Uani 1 1 d . . . . .
H5 H 0.4160 0.5512 0.1723 0.213 Uiso 1 1 calc R U . . .
C6 C 0.3339(5) 0.3718(4) 0.1613(4) 0.1903(14) Uani 1 1 d . . . . .
H6 H 0.2431 0.4126 0.0978 0.228 Uiso 1 1 calc R U . . .
C7 C 0.3615(5) 0.2298(4) 0.2083(4) 0.1635(11) Uani 1 1 d . . . . .
C8 C 0.4967(5) 0.1749(3) 0.3019(3) 0.1677(12) Uani 1 1 d . . . . .
H8 H 0.5183 0.0786 0.3356 0.201 Uiso 1 1 calc R U . . .
C9 C 0.6005(4) 0.2570(3) 0.3469(3) 0.1517(10) Uani 1 1 d . . . . .
H9 H 0.6909 0.2158 0.4105 0.182 Uiso 1 1 calc R U . . .
C10 C 0.059(3) 0.2270(16) 0.108(2) 0.191(6) Uani 0.47(2) 1 d . . P A 1
H10A H -0.0342 0.1748 0.1326 0.229 Uiso 0.47(2) 1 calc R U P A 1
H10B H 0.0049 0.3280 0.1419 0.229 Uiso 0.47(2) 1 calc R U P A 1
C11 C 0.113(4) 0.225(3) -0.042(3) 0.277(9) Uani 0.47(2) 1 d . . P A 1
H11A H -0.0024 0.2738 -0.0884 0.416 Uiso 0.47(2) 1 calc R U P A 1
H11B H 0.2075 0.2752 -0.0631 0.416 Uiso 0.47(2) 1 calc R U P A 1
H11C H 0.1688 0.1234 -0.0723 0.416 Uiso 0.47(2) 1 calc R U P A 1
C12 C 0.315(3) -0.0128(18) 0.1903(18) 0.177(5) Uani 0.47(2) 1 d . . P A 1
H12A H 0.4565 -0.0533 0.1950 0.213 Uiso 0.47(2) 1 calc R U P A 1
H12B H 0.2818 -0.0627 0.1172 0.213 Uiso 0.47(2) 1 calc R U P A 1
C13 C 0.213(5) -0.041(4) 0.321(3) 0.291(16) Uani 0.47(2) 1 d . . P A 1
H13A H 0.2517 -0.1457 0.3394 0.436 Uiso 0.47(2) 1 calc R U P A 1
H13B H 0.2480 0.0077 0.3938 0.436 Uiso 0.47(2) 1 calc R U P A 1
H13C H 0.0736 -0.0017 0.3161 0.436 Uiso 0.47(2) 1 calc R U P A 1
C10A C 0.190(3) 0.1728(15) 0.0124(18) 0.188(5) Uani 0.53(2) 1 d . . P A 2
H10C H 0.2608 0.2290 -0.0422 0.225 Uiso 0.53(2) 1 calc R U P A 2
H10D H 0.2127 0.0789 -0.0324 0.225 Uiso 0.53(2) 1 calc R U P A 2
C11A C -0.020(3) 0.2568(17) 0.028(2) 0.239(5) Uani 0.53(2) 1 d . . P A 2
H11D H -0.0694 0.2764 -0.0604 0.359 Uiso 0.53(2) 1 calc R U P A 2
H11E H -0.0888 0.2000 0.0822 0.359 Uiso 0.53(2) 1 calc R U P A 2
H11F H -0.0409 0.3493 0.0725 0.359 Uiso 0.53(2) 1 calc R U P A 2
C12A C 0.189(3) 0.034(2) 0.271(3) 0.216(7) Uani 0.53(2) 1 d . . P A 2
H12C H 0.2049 0.0522 0.3649 0.259 Uiso 0.53(2) 1 calc R U P A 2
H12D H 0.0556 0.0363 0.2628 0.259 Uiso 0.53(2) 1 calc R U P A 2
C13A C 0.333(3) -0.096(3) 0.217(3) 0.277(10) Uani 0.53(2) 1 d . . P A 2
H13D H 0.3205 -0.1817 0.2675 0.415 Uiso 0.53(2) 1 calc R U P A 2
H13E H 0.3148 -0.1060 0.1225 0.415 Uiso 0.53(2) 1 calc R U P A 2
H13F H 0.4617 -0.0903 0.2230 0.415 Uiso 0.53(2) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.42t (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.42t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42t (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C3 1.272(3) . ?
N1 C2 1.379(3) . ?
N2 C1 1.128(4) . ?
N3 C7 1.380(4) . ?
N3 C12 1.444(16) . ?
N3 C10 1.54(2) . ?
N3 C10A 1.577(16) . ?
N3 C12A 1.64(3) . ?
C1 C2 1.447(5) . ?
C2 C2 1.343(5) 2_766 ?
C3 C4 1.443(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 C9 1.379(4) . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.367(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(4) . ?
C8 C9 1.362(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.49(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.48(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10A C11A 1.46(3) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C12A C13A 1.42(3) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 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
C3 N1 C2 121.2(3) . . ?
C7 N3 C12 120.8(6) . . ?
C7 N3 C10 117.7(4) . . ?
C12 N3 C10 119.9(7) . . ?
C7 N3 C10A 119.9(5) . . ?
C7 N3 C12A 117.5(6) . . ?
C10A N3 C12A 122.0(7) . . ?
N2 C1 C2 174.5(3) . . ?
C2 C2 N1 121.6(3) 2_766 . ?
C2 C2 C1 118.1(3) 2_766 . ?
N1 C2 C1 120.3(2) . . ?
N1 C3 C4 123.1(3) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C5 C4 C9 116.7(3) . . ?
C5 C4 C3 121.0(3) . . ?
C9 C4 C3 122.3(3) . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 117.2(3) . . ?
C6 C7 N3 121.1(3) . . ?
C8 C7 N3 121.7(3) . . ?
C9 C8 C7 122.0(3) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C4 121.1(3) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C11 C10 N3 101.2(19) . . ?
C11 C10 H10A 111.5 . . ?
N3 C10 H10A 111.5 . . ?
C11 C10 H10B 111.5 . . ?
N3 C10 H10B 111.5 . . ?
H10A C10 H10B 109.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 111(3) . . ?
N3 C12 H12A 109.5 . . ?
C13 C12 H12A 109.6 . . ?
N3 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11A C10A N3 106.7(17) . . ?
C11A C10A H10C 110.4 . . ?
N3 C10A H10C 110.4 . . ?
C11A C10A H10D 110.4 . . ?
N3 C10A H10D 110.4 . . ?
H10C C10A H10D 108.6 . . ?
C10A C11A H11D 109.5 . . ?
C10A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C10A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C13A C12A N3 94(3) . . ?
C13A C12A H12C 113.0 . . ?
N3 C12A H12C 113.0 . . ?
C13A C12A H12D 113.0 . . ?
N3 C12A H12D 113.0 . . ?
H12C C12A H12D 110.4 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 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
C3 N1 C2 C2 -179.5(3) . . . 2_766 ?
C3 N1 C2 C1 0.7(4) . . . . ?
C2 N1 C3 C4 178.4(2) . . . . ?
N1 C3 C4 C5 -175.3(2) . . . . ?
N1 C3 C4 C9 3.1(5) . . . . ?
C9 C4 C5 C6 -0.1(5) . . . . ?
C3 C4 C5 C6 178.4(3) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C5 C6 C7 N3 -178.6(3) . . . . ?
C12 N3 C7 C6 168.1(11) . . . . ?
C10 N3 C7 C6 -26.6(10) . . . . ?
C10A N3 C7 C6 28.2(10) . . . . ?
C12A N3 C7 C6 -143.1(9) . . . . ?
C12 N3 C7 C8 -10.5(13) . . . . ?
C10 N3 C7 C8 154.8(8) . . . . ?
C10A N3 C7 C8 -150.4(9) . . . . ?
C12A N3 C7 C8 38.3(10) . . . . ?
C6 C7 C8 C9 -0.1(6) . . . . ?
N3 C7 C8 C9 178.6(3) . . . . ?
C7 C8 C9 C4 0.0(5) . . . . ?
C5 C4 C9 C8 0.1(5) . . . . ?
C3 C4 C9 C8 -178.3(2) . . . . ?
C7 N3 C10 C11 98.9(10) . . . . ?
C12 N3 C10 C11 -95.6(14) . . . . ?
C7 N3 C12 C13 88.4(15) . . . . ?
C10 N3 C12 C13 -76.7(12) . . . . ?
C7 N3 C10A C11A -102.5(9) . . . . ?
C12A N3 C10A C11A 68.4(12) . . . . ?
C7 N3 C12A C13A -106.3(11) . . . . ?
C10A N3 C12A C13A 82.6(11) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"N, N'-bis [(4-diethylaminophenyl) methylidene] diaminomaleonitrile"
_chemical_name_common            DE2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and diethyl ether'
