# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_SIE00870
_database_code_depnum_ccdc_archive 'CCDC 1974804'
loop_
_audit_author_name
_audit_author_address
'Illia Serdiuk'
;University of Gdansk
Poland
;
_audit_update_record             
;
2019-12-31 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H32 N4'
_chemical_formula_weight         544.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1357(6)
_cell_length_b                   13.0621(10)
_cell_length_c                   14.4197(10)
_cell_angle_alpha                102.464(4)
_cell_angle_beta                 98.192(3)
_cell_angle_gamma                92.690(4)
_cell_volume                     1476.20(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5508
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.83

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.876
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25964
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.464
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7247
_reflns_number_gt                4381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0913P)²+0.1845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7247
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1905
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.18896(17) 0.79314(11) 0.55367(10) 0.0392(4) Uani 1 1 d . . . . .
N2 N 0.55459(19) 0.63384(11) 0.18639(10) 0.0429(4) Uani 1 1 d . . . . .
N3 N 0.49672(19) 0.47342(12) 0.23128(10) 0.0428(4) Uani 1 1 d . . . . .
N4 N 0.65102(19) 0.47657(12) 0.10432(10) 0.0440(4) Uani 1 1 d . . . . .
C1 C 0.2424(2) 0.89881(13) 0.59769(11) 0.0364(4) Uani 1 1 d . . . . .
C2 C 0.3915(2) 0.94458(15) 0.58378(13) 0.0445(4) Uani 1 1 d . . . . .
H2A H 0.4578 0.9051 0.5421 0.053 Uiso 1 1 calc R U . . .
C3 C 0.4440(3) 1.04707(16) 0.63000(14) 0.0546(5) Uani 1 1 d . . . . .
H3A H 0.5464 1.0778 0.6202 0.066 Uiso 1 1 calc R U . . .
C4 C 0.3494(3) 1.10473(17) 0.69001(15) 0.0619(6) Uani 1 1 d . . . . .
H4A H 0.3861 1.1752 0.7224 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2002(3) 1.05973(15) 0.70312(15) 0.0547(5) Uani 1 1 d . . . . .
H5A H 0.1347 1.1004 0.7445 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1428(2) 0.95731(14) 0.65786(12) 0.0406(4) Uani 1 1 d . . . . .
C7 C -0.0272(2) 0.90796(15) 0.66396(14) 0.0473(5) Uani 1 1 d . . . . .
C8 C -0.0142(2) 0.79155(14) 0.66036(12) 0.0397(4) Uani 1 1 d . . . . .
C9 C -0.1100(3) 0.73421(16) 0.70700(14) 0.0519(5) Uani 1 1 d . . . . .
H9A H -0.1790 0.7704 0.7489 0.062 Uiso 1 1 calc R U . . .
C10 C -0.1081(3) 0.62648(17) 0.69457(14) 0.0576(6) Uani 1 1 d . . . . .
H10A H -0.1754 0.5893 0.7272 0.069 Uiso 1 1 calc R U . . .
C11 C -0.0078(3) 0.57366(16) 0.63443(14) 0.0537(5) Uani 1 1 d . . . . .
H11A H -0.0056 0.4995 0.6254 0.064 Uiso 1 1 calc R U . . .
C12 C 0.0893(2) 0.62772(15) 0.58720(13) 0.0458(5) Uani 1 1 d . . . . .
H12A H 0.1578 0.5906 0.5455 0.055 Uiso 1 1 calc R U . . .
C13 C 0.0879(2) 0.73611(13) 0.60002(11) 0.0369(4) Uani 1 1 d . . . . .
C14 C -0.1471(3) 0.9176(2) 0.57324(19) 0.0738(7) Uani 1 1 d . . . . .
H14A H -0.1580 0.9921 0.5736 0.111 Uiso 1 1 calc R U . . .
H14B H -0.1026 0.8837 0.5156 0.111 Uiso 1 1 calc R U . . .
H14C H -0.2567 0.8830 0.5732 0.111 Uiso 1 1 calc R U . . .
C15 C -0.0941(3) 0.96434(19) 0.7542(2) 0.0837(9) Uani 1 1 d . . . . .
H15A H -0.1005 1.0390 0.7538 0.125 Uiso 1 1 calc R U . . .
H15B H -0.2054 0.9326 0.7547 0.125 Uiso 1 1 calc R U . . .
H15C H -0.0191 0.9575 0.8117 0.125 Uiso 1 1 calc R U . . .
C16 C 0.2663(2) 0.73833(13) 0.47570(12) 0.0371(4) Uani 1 1 d . . . . .
C17 C 0.1891(2) 0.73039(14) 0.38304(12) 0.0427(4) Uani 1 1 d . . . . .
H17A H 0.0860 0.7605 0.3720 0.051 Uiso 1 1 calc R U . . .
C18 C 0.2596(2) 0.67871(15) 0.30457(12) 0.0442(4) Uani 1 1 d . . . . .
C19 C 0.4097(2) 0.63434(13) 0.32226(12) 0.0374(4) Uani 1 1 d . . . . .
C20 C 0.4905(2) 0.64354(15) 0.41649(13) 0.0459(5) Uani 1 1 d . . . . .
C21 C 0.4162(2) 0.69586(15) 0.49228(13) 0.0467(5) Uani 1 1 d . . . . .
H21A H 0.4698 0.7024 0.5565 0.056 Uiso 1 1 calc R U . . .
C22 C 0.1699(3) 0.6707(2) 0.20356(15) 0.0871(9) Uani 1 1 d . . . . .
H22A H 0.0671 0.7067 0.2063 0.131 Uiso 1 1 calc R U . . .
H22B H 0.2419 0.7036 0.1674 0.131 Uiso 1 1 calc R U . . .
H22C H 0.1424 0.5965 0.1715 0.131 Uiso 1 1 calc R U . . .
C23 C 0.6572(3) 0.6007(2) 0.43658(17) 0.0872(9) Uani 1 1 d . . . . .
H23A H 0.6915 0.5664 0.3757 0.131 Uiso 1 1 calc R U . . .
H23B H 0.7399 0.6585 0.4705 0.131 Uiso 1 1 calc R U . . .
H23C H 0.6487 0.5494 0.4766 0.131 Uiso 1 1 calc R U . . .
C24 C 0.4902(2) 0.57700(14) 0.24113(12) 0.0388(4) Uani 1 1 d . . . . .
C25 C 0.6369(2) 0.57995(14) 0.11974(12) 0.0391(4) Uani 1 1 d . . . . .
C26 C 0.5780(2) 0.42632(14) 0.16080(12) 0.0400(4) Uani 1 1 d . . . . .
C27 C 0.7236(2) 0.63964(14) 0.06221(12) 0.0414(4) Uani 1 1 d . . . . .
C28 C 0.7121(3) 0.74703(16) 0.07229(14) 0.0516(5) Uani 1 1 d . . . . .
H28A H 0.6428 0.7828 0.1143 0.062 Uiso 1 1 calc R U . . .
C29 C 0.8007(3) 0.80195(18) 0.02164(15) 0.0606(6) Uani 1 1 d . . . . .
H29A H 0.7921 0.8755 0.0290 0.073 Uiso 1 1 calc R U . . .
C30 C 0.9009(3) 0.75174(19) -0.03907(15) 0.0603(6) Uani 1 1 d . . . . .
H30A H 0.9621 0.7903 -0.0735 0.072 Uiso 1 1 calc R U . . .
C31 C 0.9128(3) 0.64529(19) -0.05020(15) 0.0595(6) Uani 1 1 d . . . . .
H31A H 0.9823 0.6103 -0.0925 0.071 Uiso 1 1 calc R U . . .
C32 C 0.8247(2) 0.58913(16) -0.00048(13) 0.0483(5) Uani 1 1 d . . . . .
H32A H 0.8329 0.5155 -0.0090 0.058 Uiso 1 1 calc R U . . .
C33 C 0.5887(2) 0.31140(14) 0.14531(13) 0.0425(4) Uani 1 1 d . . . . .
C34 C 0.6549(3) 0.25725(16) 0.06720(15) 0.0561(5) Uani 1 1 d . . . . .
H34A H 0.6954 0.2943 0.0241 0.067 Uiso 1 1 calc R U . . .
C35 C 0.6623(3) 0.14955(17) 0.05186(18) 0.0691(7) Uani 1 1 d . . . . .
H35A H 0.7065 0.1127 -0.0022 0.083 Uiso 1 1 calc R U . . .
C36 C 0.6056(3) 0.09555(17) 0.11464(18) 0.0664(6) Uani 1 1 d . . . . .
H36A H 0.6112 0.0215 0.1041 0.080 Uiso 1 1 calc R U . . .
C37 C 0.5414(3) 0.14829(17) 0.19216(16) 0.0602(6) Uani 1 1 d . . . . .
H37A H 0.5028 0.1109 0.2356 0.072 Uiso 1 1 calc R U . . .
C38 C 0.5323(3) 0.25596(16) 0.20761(14) 0.0506(5) Uani 1 1 d . . . . .
H38A H 0.4869 0.2921 0.2615 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.409(2) . ?
N1 C13 1.411(2) . ?
N1 C16 1.438(2) . ?
N2 C24 1.335(2) . ?
N2 C25 1.343(2) . ?
N3 C24 1.334(2) . ?
N3 C26 1.345(2) . ?
N4 C25 1.334(2) . ?
N4 C26 1.334(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.402(2) . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.368(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.520(3) . ?
C7 C8 1.519(3) . ?
C7 C15 1.535(3) . ?
C7 C14 1.549(3) . ?
C8 C9 1.390(2) . ?
C8 C13 1.401(2) . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.375(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.377(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.373(2) . ?
C16 C21 1.375(2) . ?
C17 C18 1.399(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.391(3) . ?
C18 C22 1.513(3) . ?
C19 C20 1.400(2) . ?
C19 C24 1.498(2) . ?
C20 C21 1.390(2) . ?
C20 C23 1.505(3) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 C27 1.479(2) . ?
C26 C33 1.478(3) . ?
C27 C28 1.388(3) . ?
C27 C32 1.391(2) . ?
C28 C29 1.377(3) . ?
C28 H28A 0.9500 . ?
C29 C30 1.366(3) . ?
C29 H29A 0.9500 . ?
C30 C31 1.375(3) . ?
C30 H30A 0.9500 . ?
C31 C32 1.375(3) . ?
C31 H31A 0.9500 . ?
C32 H32A 0.9500 . ?
C33 C38 1.382(3) . ?
C33 C34 1.387(2) . ?
C34 C35 1.382(3) . ?
C34 H34A 0.9500 . ?
C35 C36 1.376(3) . ?
C35 H35A 0.9500 . ?
C36 C37 1.366(3) . ?
C36 H36A 0.9500 . ?
C37 C38 1.383(3) . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 118.78(13) . . ?
C1 N1 C16 119.86(13) . . ?
C13 N1 C16 119.85(14) . . ?
C24 N2 C25 115.14(15) . . ?
C24 N3 C26 115.10(15) . . ?
C25 N4 C26 115.87(14) . . ?
C2 C1 C6 120.02(16) . . ?
C2 C1 N1 121.32(15) . . ?
C6 C1 N1 118.65(15) . . ?
C3 C2 C1 120.38(17) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 120.28(19) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 119.43(19) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 C6 122.05(18) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 H5A 119.0 . . ?
C5 C6 C1 117.83(17) . . ?
C5 C6 C7 123.53(16) . . ?
C1 C6 C7 118.48(15) . . ?
C8 C7 C6 108.81(14) . . ?
C8 C7 C15 112.05(16) . . ?
C6 C7 C15 111.46(17) . . ?
C8 C7 C14 107.60(16) . . ?
C6 C7 C14 107.37(16) . . ?
C15 C7 C14 109.37(19) . . ?
C9 C8 C13 117.49(17) . . ?
C9 C8 C7 123.54(16) . . ?
C13 C8 C7 118.71(15) . . ?
C10 C9 C8 122.29(18) . . ?
C10 C9 H9A 118.9 . . ?
C8 C9 H9A 118.9 . . ?
C11 C10 C9 119.17(18) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C12 120.27(19) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C11 C12 C13 120.52(17) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C12 C13 C8 120.25(16) . . ?
C12 C13 N1 121.34(15) . . ?
C8 C13 N1 118.41(15) . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 119.86(15) . . ?
C17 C16 N1 118.76(15) . . ?
C21 C16 N1 121.37(15) . . ?
C16 C17 C18 121.08(16) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
C19 C18 C17 118.55(16) . . ?
C19 C18 C22 121.93(16) . . ?
C17 C18 C22 119.51(17) . . ?
C18 C19 C20 120.67(15) . . ?
C18 C19 C24 120.92(15) . . ?
C20 C19 C24 118.40(15) . . ?
C21 C20 C19 118.84(16) . . ?
C21 C20 C23 119.87(17) . . ?
C19 C20 C23 121.27(16) . . ?
C16 C21 C20 120.98(17) . . ?
C16 C21 H21A 119.5 . . ?
C20 C21 H21A 119.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 N2 125.11(15) . . ?
N3 C24 C19 117.26(15) . . ?
N2 C24 C19 117.60(15) . . ?
N4 C25 N2 124.36(16) . . ?
N4 C25 C27 117.63(15) . . ?
N2 C25 C27 117.96(16) . . ?
N4 C26 N3 124.35(16) . . ?
N4 C26 C33 117.66(15) . . ?
N3 C26 C33 117.99(16) . . ?
C28 C27 C32 118.67(17) . . ?
C28 C27 C25 121.24(16) . . ?
C32 C27 C25 120.04(17) . . ?
C29 C28 C27 120.24(18) . . ?
C29 C28 H28A 119.9 . . ?
C27 C28 H28A 119.9 . . ?
C30 C29 C28 120.6(2) . . ?
C30 C29 H29A 119.7 . . ?
C28 C29 H29A 119.7 . . ?
C29 C30 C31 119.79(19) . . ?
C29 C30 H30A 120.1 . . ?
C31 C30 H30A 120.1 . . ?
C30 C31 C32 120.37(19) . . ?
C30 C31 H31A 119.8 . . ?
C32 C31 H31A 119.8 . . ?
C31 C32 C27 120.31(19) . . ?
C31 C32 H32A 119.8 . . ?
C27 C32 H32A 119.8 . . ?
C38 C33 C34 118.87(18) . . ?
C38 C33 C26 120.85(16) . . ?
C34 C33 C26 120.28(17) . . ?
C35 C34 C33 120.2(2) . . ?
C35 C34 H34A 119.9 . . ?
C33 C34 H34A 119.9 . . ?
C36 C35 C34 120.2(2) . . ?
C36 C35 H35A 119.9 . . ?
C34 C35 H35A 119.9 . . ?
C37 C36 C35 120.0(2) . . ?
C37 C36 H36A 120.0 . . ?
C35 C36 H36A 120.0 . . ?
C36 C37 C38 120.2(2) . . ?
C36 C37 H37A 119.9 . . ?
C38 C37 H37A 119.9 . . ?
C33 C38 C37 120.52(19) . . ?
C33 C38 H38A 119.7 . . ?
C37 C38 H38A 119.7 . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_SIE00908
_database_code_depnum_ccdc_archive 'CCDC 1974805'
loop_
_audit_author_name
_audit_author_address
'Illia Serdiuk'
;University of Gdansk
Poland
;
_audit_update_record             
;
2019-12-31 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H40 N4'
_chemical_formula_weight         600.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   8.2564(4)
_cell_length_b                   15.5077(7)
_cell_length_c                   26.3790(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3377.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6869
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      26.35

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.181
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33248
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.523
_diffrn_reflns_theta_max         28.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4364
_reflns_number_gt                3283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1211P)²+1.3817P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4364
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.2135
_refine_ls_wR_factor_gt          0.1882
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4515(2) 0.2500 0.56400(7) 0.0288(4) Uani 1 2 d S T P . .
N2 N 0.96777(18) 0.32599(9) 0.38788(5) 0.0318(3) Uani 1 1 d . . . . .
N3 N 1.1370(2) 0.2500 0.33064(7) 0.0299(4) Uani 1 2 d S T P . .
C1 C 0.37497(19) 0.17189(10) 0.57707(6) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.3995(2) 0.09729(12) 0.54863(7) 0.0386(4) Uani 1 1 d . . . . .
H2A H 0.4714 0.0982 0.5205 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3199(3) 0.02235(13) 0.56114(9) 0.0506(5) Uani 1 1 d . . . . .
H3A H 0.3383 -0.0285 0.5419 0.061 Uiso 1 1 calc R U . . .
C4 C 0.2140(3) 0.02049(14) 0.60116(9) 0.0560(6) Uani 1 1 d . . . . .
H4A H 0.1567 -0.0309 0.6091 0.067 Uiso 1 1 calc R U . . .
C5 C 0.1914(3) 0.09414(13) 0.62978(8) 0.0435(5) Uani 1 1 d . . . . .
H5A H 0.1187 0.0924 0.6577 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2715(2) 0.17035(11) 0.61907(6) 0.0289(4) Uani 1 1 d . . . . .
C7 C 0.2610(3) 0.2500 0.65244(9) 0.0313(5) Uani 1 2 d S T P . .
C8 C 0.4096(4) 0.2500 0.68783(10) 0.0478(7) Uani 1 2 d S T P . .
H8A H 0.5068 0.2500 0.6679 0.072 Uiso 1 2 d R U P . .
H8B H 0.4073 0.3006 0.7088 0.072 Uiso 1 1 d R U . . .
C9 C 0.1073(4) 0.2500 0.68500(12) 0.0519(8) Uani 1 2 d S T P . .
H9A H 0.0143 0.2500 0.6632 0.078 Uiso 1 2 d R U P . .
H9B H 0.1055 0.1995 0.7060 0.078 Uiso 1 1 d R U . . .
C10 C 0.5672(3) 0.2500 0.52348(8) 0.0279(5) Uani 1 2 d S T P . .
C11 C 0.5185(3) 0.2500 0.47346(9) 0.0356(6) Uani 1 2 d S T P . .
H11A H 0.4061 0.2500 0.4657 0.043 Uiso 1 2 calc R U P . .
C12 C 0.6300(3) 0.2500 0.43442(9) 0.0340(6) Uani 1 2 d S T P . .
C13 C 0.7946(3) 0.2500 0.44658(8) 0.0267(5) Uani 1 2 d S T P . .
C14 C 0.8456(3) 0.2500 0.49664(10) 0.0396(6) Uani 1 2 d S T P . .
C15 C 0.7291(3) 0.2500 0.53487(9) 0.0385(6) Uani 1 2 d S T P . .
H15A H 0.7625 0.2500 0.5693 0.046 Uiso 1 2 calc R U P . .
C16 C 0.5751(4) 0.2500 0.38003(11) 0.0756(14) Uani 1 2 d S T P . .
H16A H 0.4589 0.2500 0.3790 0.113 Uiso 1 2 d R U P . .
H16B H 0.6154 0.3006 0.3632 0.113 Uiso 1 1 d R U . . .
C17 C 1.0232(4) 0.2500 0.50996(13) 0.0836(15) Uani 1 2 d S T P . .
H17A H 1.0869 0.2500 0.4795 0.125 Uiso 1 2 d R U P . .
H17B H 1.0477 0.3006 0.5295 0.125 Uiso 1 1 d R U . . .
C18 C 0.9177(3) 0.2500 0.40498(8) 0.0263(5) Uani 1 2 d S T P . .
C19 C 1.0780(2) 0.32275(11) 0.35054(6) 0.0277(4) Uani 1 1 d . . . . .
C20 C 1.1375(2) 0.40746(11) 0.33117(6) 0.0313(4) Uani 1 1 d . . . . .
C21 C 1.2169(3) 0.46387(13) 0.36420(7) 0.0416(5) Uani 1 1 d . . . . .
C22 C 1.2710(3) 0.54254(15) 0.34549(9) 0.0536(6) Uani 1 1 d . . . . .
H22A H 1.3283 0.5806 0.3673 0.064 Uiso 1 1 calc R U . . .
C23 C 1.2432(3) 0.56602(15) 0.29629(10) 0.0562(6) Uani 1 1 d . . . . .
H23A H 1.2805 0.6202 0.2842 0.067 Uiso 1 1 calc R U . . .
C24 C 1.1613(3) 0.51138(15) 0.26425(8) 0.0507(6) Uani 1 1 d . . . . .
H24A H 1.1401 0.5290 0.2304 0.061 Uiso 1 1 calc R U . . .
C25 C 1.1090(2) 0.43074(13) 0.28060(7) 0.0377(4) Uani 1 1 d . . . . .
C26 C 1.0237(3) 0.37155(16) 0.24444(8) 0.0550(6) Uani 1 1 d . . . . .
H26A H 0.9953 0.3179 0.2619 0.082 Uiso 1 1 calc R U . . .
H26B H 0.9249 0.3995 0.2320 0.082 Uiso 1 1 calc R U . . .
H26C H 1.0952 0.3586 0.2158 0.082 Uiso 1 1 calc R U . . .
C27 C 1.2480(3) 0.44191(18) 0.41895(9) 0.0648(7) Uani 1 1 d . . . . .
H27A H 1.2031 0.3848 0.4265 0.097 Uiso 1 1 calc R U . . .
H27B H 1.3650 0.4415 0.4253 0.097 Uiso 1 1 calc R U . . .
H27C H 1.1963 0.4851 0.4407 0.097 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4090(18) 7_565 ?
N1 C1 1.4090(18) . ?
N1 C10 1.434(3) . ?
N2 C18 1.3279(17) . ?
N2 C19 1.342(2) . ?
N3 C19 1.3363(19) 7_565 ?
N3 C19 1.3363(19) . ?
C1 C2 1.394(2) . ?
C1 C6 1.400(2) . ?
C2 C3 1.375(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.371(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.519(2) . ?
C7 C6 1.519(2) 7_565 ?
C7 C9 1.532(4) . ?
C7 C8 1.542(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9599 . ?
C9 H9A 0.9599 . ?
C9 H9B 0.9602 . ?
C10 C15 1.370(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.382(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.396(3) . ?
C12 C16 1.505(4) . ?
C13 C14 1.386(3) . ?
C13 C18 1.496(3) . ?
C14 C15 1.393(3) . ?
C14 C17 1.508(4) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C18 N2 1.3279(17) 7_565 ?
C19 C20 1.493(2) . ?
C20 C21 1.398(3) . ?
C20 C25 1.402(2) . ?
C21 C22 1.390(3) . ?
C21 C27 1.506(3) . ?
C22 C23 1.368(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.374(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.391(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.499(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 118.56(18) 7_565 . ?
C1 N1 C10 118.77(10) 7_565 . ?
C1 N1 C10 118.77(9) . . ?
C18 N2 C19 115.30(15) . . ?
C19 N3 C19 115.18(19) 7_565 . ?
C2 C1 C6 120.06(15) . . ?
C2 C1 N1 121.11(15) . . ?
C6 C1 N1 118.83(15) . . ?
C3 C2 C1 120.18(17) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C4 C3 C2 120.49(19) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 119.30(19) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C6 122.03(18) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 H5A 119.0 . . ?
C5 C6 C1 117.90(16) . . ?
C5 C6 C7 123.32(16) . . ?
C1 C6 C7 118.65(15) . . ?
C6 C7 C6 108.80(19) . 7_565 ?
C6 C7 C9 111.83(14) . . ?
C6 C7 C9 111.83(14) 7_565 . ?
C6 C7 C8 107.79(15) . . ?
C6 C7 C8 107.79(15) 7_565 . ?
C9 C7 C8 108.6(2) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C9 H9A 109.0 . . ?
C7 C9 H9B 109.7 . . ?
H9A C9 H9B 109.5 . . ?
C15 C10 C11 119.6(2) . . ?
C15 C10 N1 119.1(2) . . ?
C11 C10 N1 121.3(2) . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C11 C12 C13 118.5(2) . . ?
C11 C12 C16 120.7(2) . . ?
C13 C12 C16 120.8(2) . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 C18 119.5(2) . . ?
C12 C13 C18 119.5(2) . . ?
C13 C14 C15 118.7(2) . . ?
C13 C14 C17 121.2(2) . . ?
C15 C14 C17 120.2(2) . . ?
C10 C15 C14 121.0(2) . . ?
C10 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C12 C16 H16A 109.1 . . ?
C12 C16 H16B 109.6 . . ?
H16A C16 H16B 109.5 . . ?
C14 C17 H17A 109.8 . . ?
C14 C17 H17B 109.3 . . ?
H17A C17 H17B 109.5 . . ?
N2 C18 N2 125.1(2) 7_565 . ?
N2 C18 C13 117.45(10) 7_565 . ?
N2 C18 C13 117.45(10) . . ?
N3 C19 N2 124.56(15) . . ?
N3 C19 C20 119.24(14) . . ?
N2 C19 C20 116.20(14) . . ?
C21 C20 C25 120.71(17) . . ?
C21 C20 C19 119.45(16) . . ?
C25 C20 C19 119.82(16) . . ?
C22 C21 C20 118.60(19) . . ?
C22 C21 C27 119.0(2) . . ?
C20 C21 C27 122.43(18) . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22A 119.4 . . ?
C21 C22 H22A 119.4 . . ?
C22 C23 C24 120.1(2) . . ?
C22 C23 H23A 119.9 . . ?
C24 C23 H23A 119.9 . . ?
C23 C24 C25 121.07(19) . . ?
C23 C24 H24A 119.5 . . ?
C25 C24 H24A 119.5 . . ?
C24 C25 C20 118.31(18) . . ?
C24 C25 C26 119.92(18) . . ?
C20 C25 C26 121.77(17) . . ?
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 . . ?
C21 C27 H27A 109.5 . . ?
C21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.068

