# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_dd19020_0m
_database_code_depnum_ccdc_archive 'CCDC 1940020'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University 
China
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H32 N4'
_chemical_formula_weight         532.66

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.951(2)
_cell_length_b                   10.159(2)
_cell_length_c                   26.604(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.365(7)
_cell_angle_gamma                90
_cell_volume                     2920.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2594
_cell_measurement_theta_min      5.071
_cell_measurement_theta_max      52.958

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2992
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            12707
_diffrn_reflns_av_unetI/netI     0.1080
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.535
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             5102
_reflns_number_gt                2877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

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

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1288P)²+0.2553P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5102
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0831
_refine_ls_wR_factor_ref         0.2602
_refine_ls_wR_factor_gt          0.2060
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.1336(3) 0.0598(3) 0.41360(13) 0.0653(9) Uani 1 1 d . . . . .
N2 N 0.1885(3) 0.2584(3) 0.45407(11) 0.0528(8) Uani 1 1 d . . . . .
N3 N 0.7582(4) 0.2514(4) 0.51681(15) 0.0819(12) Uani 1 1 d . . . . .
N4 N 0.4762(3) 0.7034(3) 0.70183(11) 0.0552(8) Uani 1 1 d . . . . .
C1 C 0.1616(4) -0.0495(4) 0.38825(17) 0.0714(12) Uani 1 1 d . . . . .
C2 C 0.2779(4) -0.0732(4) 0.37865(14) 0.0656(12) Uani 1 1 d . . . . .
H2 H 0.2915 -0.1400 0.3563 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3774(4) 0.0033(4) 0.40253(13) 0.0534(10) Uani 1 1 d . . . . .
C4 C 0.5021(4) -0.0301(4) 0.40041(14) 0.0590(10) Uani 1 1 d . . . . .
H4 H 0.5177 -0.0976 0.3787 0.071 Uiso 1 1 calc R U . . .
C5 C 0.5997(4) 0.0317(4) 0.42851(14) 0.0584(11) Uani 1 1 d . . . . .
C6 C 0.5744(3) 0.1335(4) 0.46203(12) 0.0480(9) Uani 1 1 d . . . . .
C7 C 0.4536(3) 0.1726(3) 0.46521(11) 0.0450(9) Uani 1 1 d . . . . .
C8 C 0.3524(3) 0.1121(3) 0.43362(12) 0.0473(9) Uani 1 1 d . . . . .
C9 C 0.2231(3) 0.1432(4) 0.43251(13) 0.0499(9) Uani 1 1 d . . . . .
C10 C 0.0542(5) -0.1399(5) 0.3709(2) 0.1016(18) Uani 1 1 d . . . . .
H10A H 0.0268 -0.1785 0.4001 0.152 Uiso 1 1 calc R U . . .
H10B H 0.0796 -0.2082 0.3500 0.152 Uiso 1 1 calc R U . . .
H10C H -0.0124 -0.0907 0.3517 0.152 Uiso 1 1 calc R U . . .
C11 C 0.7317(4) -0.0101(5) 0.42715(17) 0.0815(14) Uani 1 1 d . . . . .
H11A H 0.7753 0.0605 0.4138 0.122 Uiso 1 1 calc R U . . .
H11B H 0.7319 -0.0861 0.4057 0.122 Uiso 1 1 calc R U . . .
H11C H 0.7719 -0.0311 0.4610 0.122 Uiso 1 1 calc R U . . .
C12 C 0.6749(4) 0.1987(4) 0.49268(14) 0.0579(10) Uani 1 1 d . . . . .
C13 C 0.2282(3) 0.3835(4) 0.43532(15) 0.0577(10) Uani 1 1 d . . . . .
H13A H 0.3063 0.3713 0.4232 0.069 Uiso 1 1 calc R U . . .
H13B H 0.2414 0.4465 0.4631 0.069 Uiso 1 1 calc R U . . .
C14 C 0.1329(4) 0.4381(5) 0.39230(17) 0.0733(12) Uani 1 1 d . . . . .
H14A H 0.1593 0.5242 0.3826 0.088 Uiso 1 1 calc R U . . .
H14B H 0.1274 0.3806 0.3629 0.088 Uiso 1 1 calc R U . . .
C15 C 0.0064(4) 0.4495(5) 0.4081(2) 0.0876(15) Uani 1 1 d . . . . .
H15A H 0.0091 0.5148 0.4349 0.105 Uiso 1 1 calc R U . . .
H15B H -0.0537 0.4780 0.3793 0.105 Uiso 1 1 calc R U . . .
C16 C -0.0321(4) 0.3179(5) 0.42708(19) 0.0820(14) Uani 1 1 d . . . . .
H16A H -0.1096 0.3277 0.4399 0.098 Uiso 1 1 calc R U . . .
H16B H -0.0451 0.2556 0.3991 0.098 Uiso 1 1 calc R U . . .
C17 C 0.0657(4) 0.2662(5) 0.46870(16) 0.0691(12) Uani 1 1 d . . . . .
H17A H 0.0699 0.3229 0.4983 0.083 Uiso 1 1 calc R U . . .
H17B H 0.0416 0.1791 0.4784 0.083 Uiso 1 1 calc R U . . .
C18 C 0.4401(3) 0.2675(4) 0.50364(13) 0.0492(9) Uani 1 1 d . . . . .
C19 C 0.4443(3) 0.3431(4) 0.53844(13) 0.0513(9) Uani 1 1 d . . . . .
C20 C 0.4502(3) 0.4334(3) 0.58010(12) 0.0452(9) Uani 1 1 d . . . . .
C21 C 0.5521(3) 0.4336(4) 0.61884(13) 0.0498(9) Uani 1 1 d . . . . .
H21 H 0.6159 0.3738 0.6176 0.060 Uiso 1 1 calc R U . . .
C22 C 0.5607(3) 0.5205(4) 0.65915(13) 0.0501(9) Uani 1 1 d . . . . .
H22 H 0.6286 0.5174 0.6851 0.060 Uiso 1 1 calc R U . . .
C23 C 0.4677(3) 0.6128(4) 0.66089(12) 0.0470(9) Uani 1 1 d . . . . .
C24 C 0.3660(3) 0.6134(4) 0.62286(13) 0.0542(10) Uani 1 1 d . . . . .
H24 H 0.3029 0.6740 0.6240 0.065 Uiso 1 1 calc R U . . .
C25 C 0.3570(3) 0.5244(4) 0.58297(13) 0.0530(9) Uani 1 1 d . . . . .
H25 H 0.2875 0.5256 0.5577 0.064 Uiso 1 1 calc R U . . .
C26 C 0.5906(3) 0.7483(3) 0.72807(12) 0.0472(9) Uani 1 1 d . . . . .
C27 C 0.6888(4) 0.7744(4) 0.70278(14) 0.0569(10) Uani 1 1 d . . . . .
H27 H 0.6791 0.7644 0.6676 0.068 Uiso 1 1 calc R U . . .
C28 C 0.8008(4) 0.8151(4) 0.72942(16) 0.0657(11) Uani 1 1 d . . . . .
H28 H 0.8666 0.8303 0.7120 0.079 Uiso 1 1 calc R U . . .
C29 C 0.8172(4) 0.8335(4) 0.78098(17) 0.0722(12) Uani 1 1 d . . . . .
H29 H 0.8935 0.8605 0.7986 0.087 Uiso 1 1 calc R U . . .
C30 C 0.7197(4) 0.8116(4) 0.80641(15) 0.0686(12) Uani 1 1 d . . . . .
H30 H 0.7299 0.8250 0.8414 0.082 Uiso 1 1 calc R U . . .
C31 C 0.6060(4) 0.7697(4) 0.78044(14) 0.0579(10) Uani 1 1 d . . . . .
H31 H 0.5403 0.7559 0.7980 0.069 Uiso 1 1 calc R U . . .
C32 C 0.3651(3) 0.7598(4) 0.71392(13) 0.0494(9) Uani 1 1 d . . . . .
C33 C 0.3447(3) 0.8929(4) 0.71010(14) 0.0565(10) Uani 1 1 d . . . . .
H33 H 0.4041 0.9471 0.6995 0.068 Uiso 1 1 calc R U . . .
C34 C 0.2374(4) 0.9475(5) 0.72170(17) 0.0715(12) Uani 1 1 d . . . . .
H34 H 0.2251 1.0381 0.7194 0.086 Uiso 1 1 calc R U . . .
C35 C 0.1500(4) 0.8688(6) 0.73654(19) 0.0878(15) Uani 1 1 d . . . . .
H35 H 0.0770 0.9052 0.7439 0.105 Uiso 1 1 calc R U . . .
C36 C 0.1690(5) 0.7346(6) 0.7407(2) 0.0968(17) Uani 1 1 d . . . . .
H36 H 0.1088 0.6811 0.7510 0.116 Uiso 1 1 calc R U . . .
C37 C 0.2771(4) 0.6792(5) 0.72960(18) 0.0791(13) Uani 1 1 d . . . . .
H37 H 0.2901 0.5889 0.7327 0.095 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 C9 1.331(5) . ?
N1 C1 1.360(5) . ?
N2 C9 1.383(4) . ?
N2 C13 1.457(5) . ?
N2 C17 1.463(5) . ?
N3 C12 1.158(5) . ?
N4 C26 1.408(4) . ?
N4 C23 1.417(4) . ?
N4 C32 1.428(4) . ?
C1 C2 1.361(6) . ?
C1 C10 1.504(6) . ?
C2 C3 1.403(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.418(5) . ?
C3 C8 1.433(5) . ?
C4 C5 1.354(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.422(5) . ?
C5 C11 1.512(5) . ?
C6 C7 1.397(5) . ?
C6 C12 1.422(5) . ?
C7 C8 1.418(5) . ?
C7 C18 1.430(5) . ?
C8 C9 1.446(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.523(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.516(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.513(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.505(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.198(5) . ?
C19 C20 1.432(5) . ?
C20 C25 1.388(5) . ?
C20 C21 1.390(5) . ?
C21 C22 1.381(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(4) . ?
C24 C25 1.385(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.384(5) . ?
C26 C31 1.393(5) . ?
C27 C28 1.376(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.367(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.389(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.371(5) . ?
C32 C37 1.380(5) . ?
C33 C34 1.379(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.355(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.381(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.385(7) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 119.7(4) . . ?
C9 N2 C13 118.6(3) . . ?
C9 N2 C17 118.8(3) . . ?
C13 N2 C17 112.5(3) . . ?
C26 N4 C23 122.2(3) . . ?
C26 N4 C32 118.7(3) . . ?
C23 N4 C32 118.9(3) . . ?
N1 C1 C2 122.1(4) . . ?
N1 C1 C10 115.0(4) . . ?
C2 C1 C10 122.9(4) . . ?
C1 C2 C3 119.9(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 122.1(4) . . ?
C2 C3 C8 118.8(4) . . ?
C4 C3 C8 118.9(4) . . ?
C5 C4 C3 123.1(3) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C4 C5 C6 117.8(3) . . ?
C4 C5 C11 121.9(4) . . ?
C6 C5 C11 120.2(4) . . ?
C7 C6 C5 121.9(3) . . ?
C7 C6 C12 119.0(3) . . ?
C5 C6 C12 119.1(3) . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 C18 116.4(3) . . ?
C8 C7 C18 123.6(3) . . ?
C7 C8 C3 118.1(3) . . ?
C7 C8 C9 125.9(3) . . ?
C3 C8 C9 115.8(3) . . ?
N1 C9 N2 117.5(3) . . ?
N1 C9 C8 121.8(3) . . ?
N2 C9 C8 120.6(3) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C6 178.6(4) . . ?
N2 C13 C14 111.6(3) . . ?
N2 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 111.4(4) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 110.0(4) . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 110.5(4) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N2 C17 C16 113.5(3) . . ?
N2 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
N2 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C7 171.5(4) . . ?
C18 C19 C20 179.6(4) . . ?
C25 C20 C21 117.8(3) . . ?
C25 C20 C19 121.9(3) . . ?
C21 C20 C19 120.3(3) . . ?
C22 C21 C20 121.4(3) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 N4 120.3(3) . . ?
C22 C23 N4 120.4(3) . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 121.0(3) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
C27 C26 C31 118.6(4) . . ?
C27 C26 N4 121.4(3) . . ?
C31 C26 N4 120.0(3) . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 121.2(4) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 119.2(4) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C29 C30 C31 120.7(4) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C30 C31 C26 119.9(4) . . ?
C30 C31 H31 120.0 . . ?
C26 C31 H31 120.0 . . ?
C33 C32 C37 119.6(4) . . ?
C33 C32 N4 120.9(3) . . ?
C37 C32 N4 119.4(4) . . ?
C32 C33 C34 121.0(4) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C35 C34 C33 119.7(4) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.1(4) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C37 120.5(4) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C32 C37 C36 119.1(5) . . ?
C32 C37 H37 120.5 . . ?
C36 C37 H37 120.5 . . ?

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
C9 N1 C1 C2 -4.1(6) . . . . ?
C9 N1 C1 C10 177.0(4) . . . . ?
N1 C1 C2 C3 11.2(6) . . . . ?
C10 C1 C2 C3 -170.0(4) . . . . ?
C1 C2 C3 C4 169.7(4) . . . . ?
C1 C2 C3 C8 -4.8(6) . . . . ?
C2 C3 C4 C5 -171.0(4) . . . . ?
C8 C3 C4 C5 3.6(6) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C3 C4 C5 C11 177.3(4) . . . . ?
C4 C5 C6 C7 -2.0(5) . . . . ?
C11 C5 C6 C7 -178.5(4) . . . . ?
C4 C5 C6 C12 179.0(3) . . . . ?
C11 C5 C6 C12 2.4(5) . . . . ?
C5 C6 C7 C8 -1.4(5) . . . . ?
C12 C6 C7 C8 177.7(3) . . . . ?
C5 C6 C7 C18 174.4(3) . . . . ?
C12 C6 C7 C18 -6.5(5) . . . . ?
C6 C7 C8 C3 5.7(5) . . . . ?
C18 C7 C8 C3 -169.8(3) . . . . ?
C6 C7 C8 C9 -179.5(3) . . . . ?
C18 C7 C8 C9 5.0(6) . . . . ?
C2 C3 C8 C7 168.0(3) . . . . ?
C4 C3 C8 C7 -6.7(5) . . . . ?
C2 C3 C8 C9 -7.4(5) . . . . ?
C4 C3 C8 C9 177.9(3) . . . . ?
C1 N1 C9 N2 174.5(3) . . . . ?
C1 N1 C9 C8 -9.3(6) . . . . ?
C13 N2 C9 N1 -125.1(4) . . . . ?
C17 N2 C9 N1 17.9(5) . . . . ?
C13 N2 C9 C8 58.7(4) . . . . ?
C17 N2 C9 C8 -158.4(3) . . . . ?
C7 C8 C9 N1 -160.2(3) . . . . ?
C3 C8 C9 N1 14.7(5) . . . . ?
C7 C8 C9 N2 15.8(5) . . . . ?
C3 C8 C9 N2 -169.2(3) . . . . ?
C9 N2 C13 C14 91.4(4) . . . . ?
C17 N2 C13 C14 -53.7(4) . . . . ?
N2 C13 C14 C15 54.7(5) . . . . ?
C13 C14 C15 C16 -55.0(5) . . . . ?
C14 C15 C16 C17 54.2(5) . . . . ?
C9 N2 C17 C16 -90.6(4) . . . . ?
C13 N2 C17 C16 54.4(5) . . . . ?
C15 C16 C17 N2 -54.5(5) . . . . ?
C25 C20 C21 C22 0.4(5) . . . . ?
C19 C20 C21 C22 179.3(3) . . . . ?
C20 C21 C22 C23 -1.7(5) . . . . ?
C21 C22 C23 C24 1.9(5) . . . . ?
C21 C22 C23 N4 -179.4(3) . . . . ?
C26 N4 C23 C24 -151.5(3) . . . . ?
C32 N4 C23 C24 22.8(5) . . . . ?
C26 N4 C23 C22 29.8(5) . . . . ?
C32 N4 C23 C22 -155.9(3) . . . . ?
C22 C23 C24 C25 -0.8(5) . . . . ?
N4 C23 C24 C25 -179.6(3) . . . . ?
C23 C24 C25 C20 -0.5(6) . . . . ?
C21 C20 C25 C24 0.7(5) . . . . ?
C19 C20 C25 C24 -178.2(3) . . . . ?
C23 N4 C26 C27 38.1(5) . . . . ?
C32 N4 C26 C27 -136.2(4) . . . . ?
C23 N4 C26 C31 -143.0(4) . . . . ?
C32 N4 C26 C31 42.7(5) . . . . ?
C31 C26 C27 C28 2.8(6) . . . . ?
N4 C26 C27 C28 -178.3(4) . . . . ?
C26 C27 C28 C29 -1.5(6) . . . . ?
C27 C28 C29 C30 -0.4(7) . . . . ?
C28 C29 C30 C31 0.8(6) . . . . ?
C29 C30 C31 C26 0.6(6) . . . . ?
C27 C26 C31 C30 -2.4(6) . . . . ?
N4 C26 C31 C30 178.7(3) . . . . ?
C26 N4 C32 C33 57.1(5) . . . . ?
C23 N4 C32 C33 -117.4(4) . . . . ?
C26 N4 C32 C37 -123.0(4) . . . . ?
C23 N4 C32 C37 62.5(5) . . . . ?
C37 C32 C33 C34 0.0(6) . . . . ?
N4 C32 C33 C34 179.9(3) . . . . ?
C32 C33 C34 C35 -0.8(6) . . . . ?
C33 C34 C35 C36 0.9(7) . . . . ?
C34 C35 C36 C37 -0.3(8) . . . . ?
C33 C32 C37 C36 0.6(7) . . . . ?
N4 C32 C37 C36 -179.3(4) . . . . ?
C35 C36 C37 C32 -0.5(8) . . . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dd19095
_database_code_depnum_ccdc_archive 'CCDC 1940023'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University 
China
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H30 N4'
_chemical_formula_weight         530.65

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.1632(4)
_cell_length_b                   33.999(2)
_cell_length_c                   10.2383(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2841.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5971
_cell_measurement_theta_min      4.792
_cell_measurement_theta_max      54.451

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6548
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            23645
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.566
_diffrn_reflns_theta_max         25.992
_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 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5532
_reflns_number_gt                4175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.989

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

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

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.0461P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0134(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1576 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5532
_refine_ls_number_parameters     373
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.2193(4) 0.73631(9) 0.7503(3) 0.0583(8) Uani 1 1 d . . . . .
N2 N 0.1163(4) 0.66437(9) 0.1427(4) 0.0757(10) Uani 1 1 d . . . . .
N3 N -0.2031(4) 0.67049(8) 0.6922(3) 0.0525(7) Uani 1 1 d . . . . .
N4 N 0.4448(3) 0.48804(7) 0.5605(3) 0.0442(7) Uani 1 1 d . . . . .
C1 C -0.2191(5) 0.77524(11) 0.7193(4) 0.0579(10) Uani 1 1 d . . . . .
C2 C -0.1913(4) 0.78782(11) 0.5958(4) 0.0550(9) Uani 1 1 d . . . . .
H2 H -0.2046 0.8143 0.5757 0.066 Uiso 1 1 calc R U . . .
C3 C -0.1424(4) 0.76141(9) 0.4977(3) 0.0459(8) Uani 1 1 d . . . . .
C4 C -0.1023(4) 0.77422(10) 0.3707(4) 0.0528(9) Uani 1 1 d . . . . .
H4 H -0.1157 0.8007 0.3505 0.063 Uiso 1 1 calc R U . . .
C5 C -0.0450(4) 0.74980(10) 0.2764(4) 0.0517(9) Uani 1 1 d . . . . .
C6 C -0.0179(4) 0.70989(10) 0.3130(4) 0.0463(8) Uani 1 1 d . . . . .
C7 C -0.0535(4) 0.69565(9) 0.4378(3) 0.0416(8) Uani 1 1 d . . . . .
C8 C -0.1288(4) 0.72101(9) 0.5308(3) 0.0431(8) Uani 1 1 d . . . . .
C9 C -0.1849(4) 0.71029(10) 0.6591(4) 0.0485(9) Uani 1 1 d . . . . .
C10 C -0.2572(6) 0.80297(12) 0.8293(5) 0.0861(14) Uani 1 1 d . . . . .
H10A H -0.1617 0.8062 0.8830 0.129 Uiso 1 1 calc R U . . .
H10B H -0.3450 0.7924 0.8810 0.129 Uiso 1 1 calc R U . . .
H10C H -0.2893 0.8280 0.7943 0.129 Uiso 1 1 calc R U . . .
C11 C -0.0034(5) 0.76381(11) 0.1415(4) 0.0722(12) Uani 1 1 d . . . . .
H11A H -0.0613 0.7482 0.0784 0.108 Uiso 1 1 calc R U . . .
H11B H 0.1124 0.7613 0.1274 0.108 Uiso 1 1 calc R U . . .
H11C H -0.0347 0.7909 0.1325 0.108 Uiso 1 1 calc R U . . .
C12 C 0.0571(4) 0.68403(11) 0.2197(4) 0.0523(9) Uani 1 1 d . . . . .
C13 C 0.0052(4) 0.65681(9) 0.4688(3) 0.0441(8) Uani 1 1 d . . . . .
C14 C 0.0764(4) 0.62648(9) 0.4826(3) 0.0452(8) Uani 1 1 d . . . . .
C15 C 0.1665(4) 0.59084(9) 0.5024(3) 0.0427(7) Uani 1 1 d . . . . .
C16 C 0.2366(4) 0.57131(10) 0.3976(3) 0.0494(8) Uani 1 1 d . . . . .
H16 H 0.2226 0.5811 0.3135 0.059 Uiso 1 1 calc R U . . .
C17 C 0.3272(4) 0.53740(10) 0.4170(3) 0.0491(8) Uani 1 1 d . . . . .
H17 H 0.3734 0.5245 0.3458 0.059 Uiso 1 1 calc R U . . .
C18 C 0.3493(4) 0.52261(9) 0.5407(3) 0.0418(7) Uani 1 1 d . . . . .
C19 C 0.2793(4) 0.54150(10) 0.6456(3) 0.0504(9) Uani 1 1 d . . . . .
H19 H 0.2935 0.5316 0.7294 0.060 Uiso 1 1 calc R U . . .
C20 C 0.1880(4) 0.57523(10) 0.6266(3) 0.0518(9) Uani 1 1 d . . . . .
H20 H 0.1403 0.5877 0.6980 0.062 Uiso 1 1 calc R U . . .
C21 C 0.6074(4) 0.48335(9) 0.5196(3) 0.0413(8) Uani 1 1 d . . . . .
C22 C 0.7135(4) 0.51104(10) 0.4692(3) 0.0490(8) Uani 1 1 d . . . . .
H22 H 0.6797 0.5367 0.4532 0.059 Uiso 1 1 calc R U . . .
C23 C 0.8706(4) 0.49923(11) 0.4437(3) 0.0537(9) Uani 1 1 d . . . . .
H23 H 0.9453 0.5175 0.4118 0.064 Uiso 1 1 calc R U . . .
C24 C 0.9213(4) 0.46090(11) 0.4640(4) 0.0554(9) Uani 1 1 d . . . . .
H24 H 1.0279 0.4537 0.4425 0.066 Uiso 1 1 calc R U . . .
C25 C 0.8162(4) 0.43317(11) 0.5155(4) 0.0529(9) Uani 1 1 d . . . . .
H25 H 0.8511 0.4075 0.5301 0.064 Uiso 1 1 calc R U . . .
C26 C 0.6570(4) 0.44446(9) 0.5451(3) 0.0425(8) Uani 1 1 d . . . . .
C27 C 0.5204(4) 0.42492(9) 0.6062(3) 0.0421(8) Uani 1 1 d . . . . .
C28 C 0.4957(4) 0.38721(9) 0.6564(4) 0.0558(10) Uani 1 1 d . . . . .
H28 H 0.5780 0.3684 0.6513 0.067 Uiso 1 1 calc R U . . .
C29 C 0.3482(5) 0.37835(11) 0.7132(4) 0.0647(11) Uani 1 1 d . . . . .
H29 H 0.3314 0.3534 0.7475 0.078 Uiso 1 1 calc R U . . .
C30 C 0.2234(5) 0.40596(11) 0.7205(4) 0.0581(10) Uani 1 1 d . . . . .
H30 H 0.1246 0.3991 0.7595 0.070 Uiso 1 1 calc R U . . .
C31 C 0.2431(4) 0.44321(10) 0.6713(3) 0.0477(8) Uani 1 1 d . . . . .
H31 H 0.1589 0.4616 0.6756 0.057 Uiso 1 1 calc R U . . .
C32 C 0.3921(4) 0.45250(8) 0.6150(3) 0.0398(7) Uani 1 1 d . . . . .
C33 C -0.3253(4) 0.64919(11) 0.6134(4) 0.0617(10) Uani 1 1 d . . . . .
H33A H -0.3072 0.6548 0.5217 0.074 Uiso 1 1 calc R U . . .
H33B H -0.4341 0.6584 0.6361 0.074 Uiso 1 1 calc R U . . .
C34 C -0.3162(5) 0.60571(11) 0.6349(5) 0.0756(12) Uani 1 1 d . . . . .
H34A H -0.2126 0.5959 0.6018 0.091 Uiso 1 1 calc R U . . .
H34B H -0.4035 0.5929 0.5866 0.091 Uiso 1 1 calc R U . . .
C35 C -0.3314(7) 0.59542(14) 0.7780(5) 0.0907(16) Uani 1 1 d . . . . .
H35A H -0.3119 0.5675 0.7901 0.109 Uiso 1 1 calc R U . . .
H35B H -0.4413 0.6013 0.8082 0.109 Uiso 1 1 calc R U . . .
C36 C -0.2080(6) 0.61884(13) 0.8562(5) 0.0806(14) Uani 1 1 d . . . . .
H36A H -0.2232 0.6135 0.9485 0.097 Uiso 1 1 calc R U . . .
H36B H -0.0982 0.6107 0.8324 0.097 Uiso 1 1 calc R U . . .
C37 C -0.2263(5) 0.66217(11) 0.8321(4) 0.0672(11) Uani 1 1 d . . . . .
H37A H -0.3344 0.6707 0.8592 0.081 Uiso 1 1 calc R U . . .
H37B H -0.1457 0.6765 0.8829 0.081 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 C9 1.316(4) . ?
N1 C1 1.361(5) . ?
N2 C12 1.141(4) . ?
N3 C9 1.403(4) . ?
N3 C37 1.472(5) . ?
N3 C33 1.473(5) . ?
N4 C32 1.399(4) . ?
N4 C21 1.401(4) . ?
N4 C18 1.425(4) . ?
C1 C2 1.354(5) . ?
C1 C10 1.501(5) . ?
C2 C3 1.405(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(5) . ?
C3 C8 1.419(4) . ?
C4 C5 1.356(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.425(5) . ?
C5 C11 1.500(5) . ?
C6 C7 1.397(5) . ?
C6 C12 1.436(5) . ?
C7 C8 1.424(4) . ?
C7 C13 1.440(4) . ?
C8 C9 1.438(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.192(4) . ?
C14 C15 1.432(4) . ?
C15 C16 1.385(5) . ?
C15 C20 1.389(5) . ?
C16 C17 1.384(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(4) . ?
C19 C20 1.381(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.379(4) . ?
C21 C26 1.407(4) . ?
C22 C23 1.369(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.388(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.441(4) . ?
C27 C28 1.396(4) . ?
C27 C32 1.409(4) . ?
C28 C29 1.371(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.387(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.382(4) . ?
C31 H31 0.9300 . ?
C33 C34 1.497(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.511(7) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.513(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.501(5) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 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
C9 N1 C1 119.2(3) . . ?
C9 N3 C37 115.7(3) . . ?
C9 N3 C33 114.4(3) . . ?
C37 N3 C33 110.6(3) . . ?
C32 N4 C21 108.2(2) . . ?
C32 N4 C18 126.9(2) . . ?
C21 N4 C18 124.7(3) . . ?
C2 C1 N1 121.7(3) . . ?
C2 C1 C10 122.5(4) . . ?
N1 C1 C10 115.8(4) . . ?
C1 C2 C3 120.9(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 C8 118.0(3) . . ?
C4 C3 C8 120.1(3) . . ?
C5 C4 C3 123.2(3) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C4 C5 C6 116.7(3) . . ?
C4 C5 C11 122.6(3) . . ?
C6 C5 C11 120.6(3) . . ?
C7 C6 C5 122.6(3) . . ?
C7 C6 C12 119.0(3) . . ?
C5 C6 C12 118.3(3) . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 C13 116.7(3) . . ?
C8 C7 C13 123.5(3) . . ?
C3 C8 C7 117.4(3) . . ?
C3 C8 C9 116.0(3) . . ?
C7 C8 C9 126.5(3) . . ?
N1 C9 N3 117.0(3) . . ?
N1 C9 C8 123.1(3) . . ?
N3 C9 C8 119.9(3) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 177.9(4) . . ?
C14 C13 C7 169.0(4) . . ?
C13 C14 C15 177.7(4) . . ?
C16 C15 C20 118.3(3) . . ?
C16 C15 C14 120.6(3) . . ?
C20 C15 C14 121.2(3) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 N4 120.1(3) . . ?
C17 C18 N4 120.3(3) . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C22 C21 N4 129.0(3) . . ?
C22 C21 C26 122.0(3) . . ?
N4 C21 C26 108.9(3) . . ?
C23 C22 C21 117.3(3) . . ?
C23 C22 H22 121.3 . . ?
C21 C22 H22 121.3 . . ?
C22 C23 C24 121.9(3) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C25 C24 C23 121.0(3) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 118.5(3) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C25 C26 C21 119.3(3) . . ?
C25 C26 C27 133.8(3) . . ?
C21 C26 C27 106.9(3) . . ?
C28 C27 C32 118.7(3) . . ?
C28 C27 C26 134.0(3) . . ?
C32 C27 C26 107.3(3) . . ?
C29 C28 C27 119.0(3) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C30 121.3(4) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C31 C30 C29 121.2(4) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 117.8(3) . . ?
C30 C31 H31 121.1 . . ?
C32 C31 H31 121.1 . . ?
C31 C32 N4 129.4(3) . . ?
C31 C32 C27 121.9(3) . . ?
N4 C32 C27 108.7(3) . . ?
N3 C33 C34 111.8(3) . . ?
N3 C33 H33A 109.3 . . ?
C34 C33 H33A 109.3 . . ?
N3 C33 H33B 109.3 . . ?
C34 C33 H33B 109.3 . . ?
H33A C33 H33B 107.9 . . ?
C33 C34 C35 111.6(4) . . ?
C33 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
C34 C35 C36 109.7(4) . . ?
C34 C35 H35A 109.7 . . ?
C36 C35 H35A 109.7 . . ?
C34 C35 H35B 109.7 . . ?
C36 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
C37 C36 C35 111.3(4) . . ?
C37 C36 H36A 109.4 . . ?
C35 C36 H36A 109.4 . . ?
C37 C36 H36B 109.4 . . ?
C35 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?
N3 C37 C36 109.6(3) . . ?
N3 C37 H37A 109.7 . . ?
C36 C37 H37A 109.7 . . ?
N3 C37 H37B 109.7 . . ?
C36 C37 H37B 109.7 . . ?
H37A C37 H37B 108.2 . . ?

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
C9 N1 C1 C2 2.8(5) . . . . ?
C9 N1 C1 C10 -179.1(4) . . . . ?
N1 C1 C2 C3 -7.5(5) . . . . ?
C10 C1 C2 C3 174.6(4) . . . . ?
C1 C2 C3 C4 -175.8(3) . . . . ?
C1 C2 C3 C8 2.2(5) . . . . ?
C2 C3 C4 C5 175.8(3) . . . . ?
C8 C3 C4 C5 -2.1(5) . . . . ?
C3 C4 C5 C6 -3.2(5) . . . . ?
C3 C4 C5 C11 179.8(3) . . . . ?
C4 C5 C6 C7 2.4(5) . . . . ?
C11 C5 C6 C7 179.4(3) . . . . ?
C4 C5 C6 C12 -174.2(3) . . . . ?
C11 C5 C6 C12 2.9(5) . . . . ?
C5 C6 C7 C8 3.8(5) . . . . ?
C12 C6 C7 C8 -179.7(3) . . . . ?
C5 C6 C7 C13 -169.7(3) . . . . ?
C12 C6 C7 C13 6.9(5) . . . . ?
C2 C3 C8 C7 -169.8(3) . . . . ?
C4 C3 C8 C7 8.2(4) . . . . ?
C2 C3 C8 C9 6.9(4) . . . . ?
C4 C3 C8 C9 -175.1(3) . . . . ?
C6 C7 C8 C3 -8.9(4) . . . . ?
C13 C7 C8 C3 164.1(3) . . . . ?
C6 C7 C8 C9 174.8(3) . . . . ?
C13 C7 C8 C9 -12.2(5) . . . . ?
C1 N1 C9 N3 -173.6(3) . . . . ?
C1 N1 C9 C8 7.2(5) . . . . ?
C37 N3 C9 N1 -11.9(5) . . . . ?
C33 N3 C9 N1 118.4(3) . . . . ?
C37 N3 C9 C8 167.3(3) . . . . ?
C33 N3 C9 C8 -62.4(4) . . . . ?
C3 C8 C9 N1 -12.0(5) . . . . ?
C7 C8 C9 N1 164.4(3) . . . . ?
C3 C8 C9 N3 168.9(3) . . . . ?
C7 C8 C9 N3 -14.8(5) . . . . ?
C6 C7 C13 C14 38(2) . . . . ?
C8 C7 C13 C14 -135.4(19) . . . . ?
C20 C15 C16 C17 -0.8(5) . . . . ?
C14 C15 C16 C17 178.4(3) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
C16 C17 C18 N4 -179.0(3) . . . . ?
C32 N4 C18 C19 60.8(5) . . . . ?
C21 N4 C18 C19 -123.7(3) . . . . ?
C32 N4 C18 C17 -119.5(4) . . . . ?
C21 N4 C18 C17 56.0(5) . . . . ?
C17 C18 C19 C20 -0.3(5) . . . . ?
N4 C18 C19 C20 179.4(3) . . . . ?
C18 C19 C20 C15 -0.6(5) . . . . ?
C16 C15 C20 C19 1.1(5) . . . . ?
C14 C15 C20 C19 -178.0(3) . . . . ?
C32 N4 C21 C22 -174.8(3) . . . . ?
C18 N4 C21 C22 9.0(5) . . . . ?
C32 N4 C21 C26 1.5(3) . . . . ?
C18 N4 C21 C26 -174.8(3) . . . . ?
N4 C21 C22 C23 176.3(3) . . . . ?
C26 C21 C22 C23 0.4(5) . . . . ?
C21 C22 C23 C24 1.6(5) . . . . ?
C22 C23 C24 C25 -2.3(6) . . . . ?
C23 C24 C25 C26 0.9(5) . . . . ?
C24 C25 C26 C21 1.1(5) . . . . ?
C24 C25 C26 C27 -175.2(4) . . . . ?
C22 C21 C26 C25 -1.8(5) . . . . ?
N4 C21 C26 C25 -178.4(3) . . . . ?
C22 C21 C26 C27 175.5(3) . . . . ?
N4 C21 C26 C27 -1.1(3) . . . . ?
C25 C26 C27 C28 -1.4(6) . . . . ?
C21 C26 C27 C28 -178.1(4) . . . . ?
C25 C26 C27 C32 177.0(4) . . . . ?
C21 C26 C27 C32 0.4(3) . . . . ?
C32 C27 C28 C29 -0.4(5) . . . . ?
C26 C27 C28 C29 177.9(4) . . . . ?
C27 C28 C29 C30 0.6(6) . . . . ?
C28 C29 C30 C31 -0.1(6) . . . . ?
C29 C30 C31 C32 -0.6(5) . . . . ?
C30 C31 C32 N4 -178.7(3) . . . . ?
C30 C31 C32 C27 0.8(5) . . . . ?
C21 N4 C32 C31 178.2(3) . . . . ?
C18 N4 C32 C31 -5.6(5) . . . . ?
C21 N4 C32 C27 -1.3(3) . . . . ?
C18 N4 C32 C27 174.9(3) . . . . ?
C28 C27 C32 C31 -0.3(5) . . . . ?
C26 C27 C32 C31 -179.0(3) . . . . ?
C28 C27 C32 N4 179.3(3) . . . . ?
C26 C27 C32 N4 0.6(3) . . . . ?
C9 N3 C33 C34 168.9(3) . . . . ?
C37 N3 C33 C34 -58.3(4) . . . . ?
N3 C33 C34 C35 54.8(5) . . . . ?
C33 C34 C35 C36 -52.5(5) . . . . ?
C34 C35 C36 C37 55.2(5) . . . . ?
C9 N3 C37 C36 -168.0(3) . . . . ?
C33 N3 C37 C36 59.8(4) . . . . ?
C35 C36 C37 N3 -59.1(5) . . . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dd19116
_database_code_depnum_ccdc_archive 'CCDC 1940021'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University 
China
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H30 N4'
_chemical_formula_weight         530.65

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.1615(2)
_cell_length_b                   33.9887(12)
_cell_length_c                   10.2333(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2838.71(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3931
_cell_measurement_theta_min      4.794
_cell_measurement_theta_max      48.979

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6487
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            12972
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.567
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             5168
_reflns_number_gt                3944
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.960

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

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

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0164(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1469 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5168
_refine_ls_number_parameters     373
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 -0.2198(4) 0.73621(9) 0.2495(3) 0.0578(8) Uani 1 1 d . . . . .
N2 N 0.1161(4) 0.66455(9) 0.8571(4) 0.0750(10) Uani 1 1 d . . . . .
N3 N -0.2034(4) 0.67040(8) 0.3079(3) 0.0522(8) Uani 1 1 d . . . . .
N4 N 0.4447(3) 0.48811(8) 0.4399(3) 0.0443(7) Uani 1 1 d . . . . .
C1 C -0.2188(5) 0.77521(11) 0.2807(4) 0.0560(10) Uani 1 1 d . . . . .
C2 C -0.1913(4) 0.78774(11) 0.4038(4) 0.0542(9) Uani 1 1 d . . . . .
H2 H -0.2049 0.8142 0.4240 0.065 Uiso 1 1 calc R U . . .
C3 C -0.1425(4) 0.76149(10) 0.5017(4) 0.0466(8) Uani 1 1 d . . . . .
C4 C -0.1026(4) 0.77429(10) 0.6290(4) 0.0537(9) Uani 1 1 d . . . . .
H4 H -0.1167 0.8007 0.6496 0.064 Uiso 1 1 calc R U . . .
C5 C -0.0444(4) 0.74966(11) 0.7232(4) 0.0513(9) Uani 1 1 d . . . . .
C6 C -0.0178(4) 0.70997(10) 0.6865(4) 0.0449(8) Uani 1 1 d . . . . .
C7 C -0.0536(4) 0.69567(9) 0.5616(3) 0.0425(8) Uani 1 1 d . . . . .
C8 C -0.1293(4) 0.72100(10) 0.4693(3) 0.0435(8) Uani 1 1 d . . . . .
C9 C -0.1852(4) 0.71008(10) 0.3407(4) 0.0487(9) Uani 1 1 d . . . . .
C10 C -0.2574(6) 0.80285(12) 0.1700(4) 0.0838(14) Uani 1 1 d . . . . .
H10A H -0.1640 0.8049 0.1135 0.126 Uiso 1 1 calc R U . . .
H10B H -0.2838 0.8283 0.2046 0.126 Uiso 1 1 calc R U . . .
H10C H -0.3492 0.7929 0.1215 0.126 Uiso 1 1 calc R U . . .
C11 C -0.0037(5) 0.76368(11) 0.8585(4) 0.0740(12) Uani 1 1 d . . . . .
H11A H -0.0609 0.7479 0.9214 0.111 Uiso 1 1 calc R U . . .
H11B H -0.0363 0.7907 0.8678 0.111 Uiso 1 1 calc R U . . .
H11C H 0.1122 0.7615 0.8728 0.111 Uiso 1 1 calc R U . . .
C12 C 0.0569(4) 0.68393(11) 0.7796(4) 0.0527(9) Uani 1 1 d . . . . .
C13 C -0.3254(4) 0.64902(10) 0.3863(4) 0.0620(10) Uani 1 1 d . . . . .
H13A H -0.4342 0.6582 0.3633 0.074 Uiso 1 1 calc R U . . .
H13B H -0.3077 0.6547 0.4781 0.074 Uiso 1 1 calc R U . . .
C14 C -0.3159(5) 0.60567(11) 0.3652(5) 0.0745(12) Uani 1 1 d . . . . .
H14A H -0.4028 0.5929 0.4140 0.089 Uiso 1 1 calc R U . . .
H14B H -0.2120 0.5960 0.3981 0.089 Uiso 1 1 calc R U . . .
C15 C -0.3317(6) 0.59519(15) 0.2218(5) 0.0905(15) Uani 1 1 d . . . . .
H15A H -0.3120 0.5673 0.2098 0.109 Uiso 1 1 calc R U . . .
H15B H -0.4417 0.6010 0.1916 0.109 Uiso 1 1 calc R U . . .
C16 C -0.2085(6) 0.61869(13) 0.1439(5) 0.0817(14) Uani 1 1 d . . . . .
H16A H -0.0986 0.6105 0.1675 0.098 Uiso 1 1 calc R U . . .
H16B H -0.2238 0.6134 0.0515 0.098 Uiso 1 1 calc R U . . .
C17 C -0.2266(5) 0.66200(11) 0.1685(4) 0.0674(11) Uani 1 1 d . . . . .
H17A H -0.1461 0.6764 0.1176 0.081 Uiso 1 1 calc R U . . .
H17B H -0.3348 0.6706 0.1414 0.081 Uiso 1 1 calc R U . . .
C18 C 0.0054(4) 0.65687(10) 0.5315(3) 0.0432(8) Uani 1 1 d . . . . .
C19 C 0.0760(4) 0.62657(10) 0.5171(3) 0.0437(8) Uani 1 1 d . . . . .
C20 C 0.1667(4) 0.59080(9) 0.4972(3) 0.0418(8) Uani 1 1 d . . . . .
C21 C 0.2368(4) 0.57135(10) 0.6020(3) 0.0487(9) Uani 1 1 d . . . . .
H21 H 0.2230 0.5812 0.6861 0.058 Uiso 1 1 calc R U . . .
C22 C 0.3270(4) 0.53750(10) 0.5830(3) 0.0496(9) Uani 1 1 d . . . . .
H22 H 0.3733 0.5247 0.6543 0.059 Uiso 1 1 calc R U . . .
C23 C 0.3488(4) 0.52260(9) 0.4590(3) 0.0408(8) Uani 1 1 d . . . . .
C24 C 0.2794(4) 0.54150(10) 0.3545(3) 0.0518(9) Uani 1 1 d . . . . .
H24 H 0.2938 0.5316 0.2706 0.062 Uiso 1 1 calc R U . . .
C25 C 0.1882(4) 0.57523(10) 0.3734(4) 0.0526(9) Uani 1 1 d . . . . .
H25 H 0.1405 0.5877 0.3020 0.063 Uiso 1 1 calc R U . . .
C26 C 0.6073(4) 0.48331(9) 0.4804(3) 0.0397(8) Uani 1 1 d . . . . .
C27 C 0.7135(4) 0.51097(10) 0.5312(3) 0.0479(9) Uani 1 1 d . . . . .
H27 H 0.6796 0.5366 0.5476 0.057 Uiso 1 1 calc R U . . .
C28 C 0.8708(4) 0.49917(11) 0.5566(3) 0.0528(9) Uani 1 1 d . . . . .
H28 H 0.9457 0.5174 0.5885 0.063 Uiso 1 1 calc R U . . .
C29 C 0.9213(4) 0.46074(11) 0.5359(4) 0.0548(9) Uani 1 1 d . . . . .
H29 H 1.0278 0.4535 0.5574 0.066 Uiso 1 1 calc R U . . .
C30 C 0.8167(4) 0.43331(11) 0.4843(4) 0.0530(9) Uani 1 1 d . . . . .
H30 H 0.8518 0.4077 0.4695 0.064 Uiso 1 1 calc R U . . .
C31 C 0.6564(4) 0.44457(9) 0.4542(3) 0.0420(8) Uani 1 1 d . . . . .
C32 C 0.5202(4) 0.42500(9) 0.3937(3) 0.0428(8) Uani 1 1 d . . . . .
C33 C 0.4961(4) 0.38733(10) 0.3432(4) 0.0555(10) Uani 1 1 d . . . . .
H33 H 0.5791 0.3686 0.3477 0.067 Uiso 1 1 calc R U . . .
C34 C 0.3484(5) 0.37824(11) 0.2868(4) 0.0635(11) Uani 1 1 d . . . . .
H34 H 0.3316 0.3532 0.2530 0.076 Uiso 1 1 calc R U . . .
C35 C 0.2231(5) 0.40599(11) 0.2795(4) 0.0594(10) Uani 1 1 d . . . . .
H35 H 0.1240 0.3991 0.2407 0.071 Uiso 1 1 calc R U . . .
C36 C 0.2432(4) 0.44317(10) 0.3283(3) 0.0483(9) Uani 1 1 d . . . . .
H36 H 0.1591 0.4616 0.3239 0.058 Uiso 1 1 calc R U . . .
C37 C 0.3923(4) 0.45258(9) 0.3845(3) 0.0404(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.319(4) . ?
N1 C1 1.363(4) . ?
N2 C12 1.139(4) . ?
N3 C9 1.398(4) . ?
N3 C17 1.467(5) . ?
N3 C13 1.471(4) . ?
N4 C26 1.400(4) . ?
N4 C37 1.401(4) . ?
N4 C23 1.423(4) . ?
C1 C2 1.350(5) . ?
C1 C10 1.504(5) . ?
C2 C3 1.399(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.412(5) . ?
C3 C8 1.420(4) . ?
C4 C5 1.362(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.417(5) . ?
C5 C11 1.502(5) . ?
C6 C7 1.398(5) . ?
C6 C12 1.437(5) . ?
C7 C8 1.420(4) . ?
C7 C18 1.437(4) . ?
C8 C9 1.441(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.491(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.515(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.512(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.501(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.189(4) . ?
C19 C20 1.438(4) . ?
C20 C25 1.384(5) . ?
C20 C21 1.384(4) . ?
C21 C22 1.379(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(4) . ?
C24 C25 1.380(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.381(4) . ?
C26 C31 1.402(4) . ?
C27 C28 1.370(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.386(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.370(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.398(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.436(4) . ?
C32 C33 1.394(4) . ?
C32 C37 1.406(4) . ?
C33 C34 1.372(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.394(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.369(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.383(4) . ?
C36 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 119.2(3) . . ?
C9 N3 C17 115.8(3) . . ?
C9 N3 C13 114.7(3) . . ?
C17 N3 C13 110.3(3) . . ?
C26 N4 C37 108.0(2) . . ?
C26 N4 C23 125.2(3) . . ?
C37 N4 C23 126.7(2) . . ?
C2 C1 N1 121.8(3) . . ?
C2 C1 C10 122.7(4) . . ?
N1 C1 C10 115.5(4) . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 C8 118.2(3) . . ?
C4 C3 C8 119.8(3) . . ?
C5 C4 C3 122.9(3) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 C5 C6 116.8(3) . . ?
C4 C5 C11 122.3(3) . . ?
C6 C5 C11 120.8(3) . . ?
C7 C6 C5 122.8(3) . . ?
C7 C6 C12 118.8(3) . . ?
C5 C6 C12 118.4(3) . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 C18 116.4(3) . . ?
C8 C7 C18 124.0(3) . . ?
C3 C8 C7 117.7(3) . . ?
C3 C8 C9 116.1(3) . . ?
C7 C8 C9 126.1(3) . . ?
N1 C9 N3 117.2(3) . . ?
N1 C9 C8 122.7(3) . . ?
N3 C9 C8 120.1(3) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 177.1(4) . . ?
N3 C13 C14 112.0(3) . . ?
N3 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 111.6(4) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 109.3(4) . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C17 C16 C15 111.3(4) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 110.0(4) . . ?
N3 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
N3 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C7 169.6(4) . . ?
C18 C19 C20 177.7(4) . . ?
C25 C20 C21 118.3(3) . . ?
C25 C20 C19 121.2(3) . . ?
C21 C20 C19 120.4(3) . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 119.6(3) . . ?
C24 C23 N4 120.4(3) . . ?
C22 C23 N4 120.0(3) . . ?
C23 C24 C25 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 121.0(3) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
C27 C26 N4 128.9(3) . . ?
C27 C26 C31 122.2(3) . . ?
N4 C26 C31 108.9(3) . . ?
C28 C27 C26 117.4(3) . . ?
C28 C27 H27 121.3 . . ?
C26 C27 H27 121.3 . . ?
C27 C28 C29 121.7(3) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 H28 119.1 . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 118.8(3) . . ?
C29 C30 H30 120.6 . . ?
C31 C30 H30 120.6 . . ?
C30 C31 C26 118.9(3) . . ?
C30 C31 C32 133.9(3) . . ?
C26 C31 C32 107.2(3) . . ?
C33 C32 C37 118.9(3) . . ?
C33 C32 C31 134.0(3) . . ?
C37 C32 C31 107.1(3) . . ?
C34 C33 C32 119.1(3) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C33 C34 C35 121.0(4) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C36 C35 C34 121.1(3) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C37 118.1(3) . . ?
C35 C36 H36 120.9 . . ?
C37 C36 H36 120.9 . . ?
C36 C37 N4 129.5(3) . . ?
C36 C37 C32 121.8(3) . . ?
N4 C37 C32 108.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 -3.3(5) . . . . ?
C9 N1 C1 C10 179.2(3) . . . . ?
N1 C1 C2 C3 8.0(6) . . . . ?
C10 C1 C2 C3 -174.7(3) . . . . ?
C1 C2 C3 C4 175.7(3) . . . . ?
C1 C2 C3 C8 -2.6(5) . . . . ?
C2 C3 C4 C5 -175.4(3) . . . . ?
C8 C3 C4 C5 2.8(5) . . . . ?
C3 C4 C5 C6 2.7(5) . . . . ?
C3 C4 C5 C11 -179.5(3) . . . . ?
C4 C5 C6 C7 -2.0(5) . . . . ?
C11 C5 C6 C7 -179.9(3) . . . . ?
C4 C5 C6 C12 174.7(3) . . . . ?
C11 C5 C6 C12 -3.2(5) . . . . ?
C5 C6 C7 C8 -4.1(5) . . . . ?
C12 C6 C7 C8 179.2(3) . . . . ?
C5 C6 C7 C18 169.6(3) . . . . ?
C12 C6 C7 C18 -7.0(4) . . . . ?
C2 C3 C8 C7 169.5(3) . . . . ?
C4 C3 C8 C7 -8.9(5) . . . . ?
C2 C3 C8 C9 -6.6(4) . . . . ?
C4 C3 C8 C9 175.1(3) . . . . ?
C6 C7 C8 C3 9.4(4) . . . . ?
C18 C7 C8 C3 -163.8(3) . . . . ?
C6 C7 C8 C9 -175.0(3) . . . . ?
C18 C7 C8 C9 11.8(5) . . . . ?
C1 N1 C9 N3 173.9(3) . . . . ?
C1 N1 C9 C8 -6.7(5) . . . . ?
C17 N3 C9 N1 12.0(5) . . . . ?
C13 N3 C9 N1 -118.3(3) . . . . ?
C17 N3 C9 C8 -167.5(3) . . . . ?
C13 N3 C9 C8 62.3(4) . . . . ?
C3 C8 C9 N1 11.5(5) . . . . ?
C7 C8 C9 N1 -164.2(3) . . . . ?
C3 C8 C9 N3 -169.0(3) . . . . ?
C7 C8 C9 N3 15.3(5) . . . . ?
C9 N3 C13 C14 -168.7(3) . . . . ?
C17 N3 C13 C14 58.4(4) . . . . ?
N3 C13 C14 C15 -55.2(5) . . . . ?
C13 C14 C15 C16 52.6(5) . . . . ?
C14 C15 C16 C17 -54.9(5) . . . . ?
C9 N3 C17 C16 168.0(3) . . . . ?
C13 N3 C17 C16 -59.7(4) . . . . ?
C15 C16 C17 N3 59.2(5) . . . . ?
C6 C7 C18 C19 -40(2) . . . . ?
C8 C7 C18 C19 133.3(19) . . . . ?
C25 C20 C21 C22 0.6(5) . . . . ?
C19 C20 C21 C22 -178.6(3) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C22 C23 C24 -0.4(5) . . . . ?
C21 C22 C23 N4 178.8(3) . . . . ?
C26 N4 C23 C24 123.2(3) . . . . ?
C37 N4 C23 C24 -60.5(5) . . . . ?
C26 N4 C23 C22 -56.0(4) . . . . ?
C37 N4 C23 C22 120.4(4) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
N4 C23 C24 C25 -179.2(3) . . . . ?
C23 C24 C25 C20 0.8(5) . . . . ?
C21 C20 C25 C24 -1.0(5) . . . . ?
C19 C20 C25 C24 178.1(3) . . . . ?
C37 N4 C26 C27 174.7(3) . . . . ?
C23 N4 C26 C27 -8.3(5) . . . . ?
C37 N4 C26 C31 -1.7(3) . . . . ?
C23 N4 C26 C31 175.2(3) . . . . ?
N4 C26 C27 C28 -176.4(3) . . . . ?
C31 C26 C27 C28 -0.4(5) . . . . ?
C26 C27 C28 C29 -1.8(5) . . . . ?
C27 C28 C29 C30 2.5(6) . . . . ?
C28 C29 C30 C31 -0.9(5) . . . . ?
C29 C30 C31 C26 -1.2(5) . . . . ?
C29 C30 C31 C32 175.7(4) . . . . ?
C27 C26 C31 C30 1.9(5) . . . . ?
N4 C26 C31 C30 178.6(3) . . . . ?
C27 C26 C31 C32 -175.8(3) . . . . ?
N4 C26 C31 C32 0.9(4) . . . . ?
C30 C31 C32 C33 0.7(6) . . . . ?
C26 C31 C32 C33 177.9(4) . . . . ?
C30 C31 C32 C37 -177.0(4) . . . . ?
C26 C31 C32 C37 0.2(4) . . . . ?
C37 C32 C33 C34 -0.3(5) . . . . ?
C31 C32 C33 C34 -177.9(4) . . . . ?
C32 C33 C34 C35 0.0(6) . . . . ?
C33 C34 C35 C36 -0.1(6) . . . . ?
C34 C35 C36 C37 0.5(5) . . . . ?
C35 C36 C37 N4 179.3(3) . . . . ?
C35 C36 C37 C32 -0.8(5) . . . . ?
C26 N4 C37 C36 -178.4(3) . . . . ?
C23 N4 C37 C36 4.8(5) . . . . ?
C26 N4 C37 C32 1.8(4) . . . . ?
C23 N4 C37 C32 -175.1(3) . . . . ?
C33 C32 C37 C36 0.8(5) . . . . ?
C31 C32 C37 C36 178.9(3) . . . . ?
C33 C32 C37 N4 -179.4(3) . . . . ?
C31 C32 C37 N4 -1.2(4) . . . . ?

_refine_diff_density_max         0.121
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_dd19045_0m
_database_code_depnum_ccdc_archive 'CCDC 1940022'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University 
China
;
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H32 N4'
_chemical_formula_weight         532.66

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.9558(3)
_cell_length_b                   10.1374(3)
_cell_length_c                   26.5962(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.3760(10)
_cell_angle_gamma                90
_cell_volume                     2914.40(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      5.078
_cell_measurement_theta_max      54.539

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            41504
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.629
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5723
_reflns_number_gt                4161
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

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

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.5828P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0146(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5723
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.13355(14) 0.93974(14) 0.41365(6) 0.0613(4) Uani 1 1 d . . . . .
N2 N 0.75769(17) 0.74824(18) 0.51680(7) 0.0787(5) Uani 1 1 d . . . . .
N3 N 0.18897(12) 0.74189(13) 0.45433(5) 0.0501(3) Uani 1 1 d . . . . .
N4 N 0.47619(12) 0.29637(14) 0.70172(5) 0.0533(4) Uani 1 1 d . . . . .
C1 C 0.1613(2) 1.04864(18) 0.38811(7) 0.0655(5) Uani 1 1 d . . . . .
C2 C 0.2771(2) 1.07302(16) 0.37868(6) 0.0625(5) Uani 1 1 d . . . . .
H2 H 0.2904 1.1402 0.3564 0.075 Uiso 1 1 calc R U . . .
C3 C 0.37748(17) 0.99644(15) 0.40267(6) 0.0499(4) Uani 1 1 d . . . . .
C4 C 0.50116(18) 1.03049(17) 0.40027(6) 0.0573(5) Uani 1 1 d . . . . .
H4 H 0.5162 1.0982 0.3785 0.069 Uiso 1 1 calc R U . . .
C5 C 0.59968(17) 0.96852(17) 0.42849(6) 0.0545(4) Uani 1 1 d . . . . .
C6 C 0.57391(15) 0.86646(15) 0.46174(6) 0.0476(4) Uani 1 1 d . . . . .
C7 C 0.45369(15) 0.82689(14) 0.46529(5) 0.0428(4) Uani 1 1 d . . . . .
C8 C 0.35208(15) 0.88819(14) 0.43331(5) 0.0439(4) Uani 1 1 d . . . . .
C9 C 0.22311(15) 0.85741(15) 0.43264(6) 0.0473(4) Uani 1 1 d . . . . .
C10 C 0.0540(2) 1.1398(2) 0.37127(10) 0.0996(8) Uani 1 1 d . . . . .
H10A H -0.0136 1.0905 0.3527 0.149 Uiso 1 1 calc R U . . .
H10B H 0.0787 1.2074 0.3498 0.149 Uiso 1 1 calc R U . . .
H10C H 0.0283 1.1794 0.4006 0.149 Uiso 1 1 calc R U . . .
C11 C 0.73094(19) 1.0100(2) 0.42701(8) 0.0773(6) Uani 1 1 d . . . . .
H11A H 0.7694 1.0373 0.4604 0.116 Uiso 1 1 calc R U . . .
H11B H 0.7312 1.0820 0.4036 0.116 Uiso 1 1 calc R U . . .
H11C H 0.7760 0.9371 0.4161 0.116 Uiso 1 1 calc R U . . .
C12 C 0.67544(17) 0.80136(18) 0.49297(7) 0.0557(4) Uani 1 1 d . . . . .
C13 C 0.22801(16) 0.61588(16) 0.43530(7) 0.0546(4) Uani 1 1 d . . . . .
H13A H 0.2406 0.5524 0.4630 0.066 Uiso 1 1 calc R U . . .
H13B H 0.3063 0.6277 0.4233 0.066 Uiso 1 1 calc R U . . .
C14 C 0.13272(18) 0.5622(2) 0.39214(8) 0.0692(5) Uani 1 1 d . . . . .
H14A H 0.1277 0.6202 0.3629 0.083 Uiso 1 1 calc R U . . .
H14B H 0.1589 0.4759 0.3822 0.083 Uiso 1 1 calc R U . . .
C15 C 0.0060(2) 0.5509(2) 0.40777(9) 0.0840(7) Uani 1 1 d . . . . .
H15A H -0.0539 0.5228 0.3788 0.101 Uiso 1 1 calc R U . . .
H15B H 0.0083 0.4851 0.4344 0.101 Uiso 1 1 calc R U . . .
C16 C -0.03259(18) 0.6823(2) 0.42687(9) 0.0811(6) Uani 1 1 d . . . . .
H16A H -0.1098 0.6721 0.4398 0.097 Uiso 1 1 calc R U . . .
H16B H -0.0460 0.7448 0.3989 0.097 Uiso 1 1 calc R U . . .
C17 C 0.06588(17) 0.7350(2) 0.46876(7) 0.0664(5) Uani 1 1 d . . . . .
H17A H 0.0420 0.8226 0.4782 0.080 Uiso 1 1 calc R U . . .
H17B H 0.0697 0.6788 0.4985 0.080 Uiso 1 1 calc R U . . .
C18 C 0.43994(15) 0.73248(15) 0.50373(6) 0.0459(4) Uani 1 1 d . . . . .
C19 C 0.44416(15) 0.65641(15) 0.53844(6) 0.0472(4) Uani 1 1 d . . . . .
C20 C 0.45017(15) 0.56664(14) 0.58002(5) 0.0441(4) Uani 1 1 d . . . . .
C21 C 0.55242(15) 0.56680(15) 0.61892(6) 0.0470(4) Uani 1 1 d . . . . .
H21 H 0.6159 0.6271 0.6178 0.056 Uiso 1 1 calc R U . . .
C22 C 0.56079(15) 0.47939(15) 0.65881(6) 0.0475(4) Uani 1 1 d . . . . .
H22 H 0.6293 0.4823 0.6846 0.057 Uiso 1 1 calc R U . . .
C23 C 0.46850(14) 0.38664(15) 0.66128(6) 0.0445(4) Uani 1 1 d . . . . .
C24 C 0.36577(15) 0.38681(16) 0.62263(6) 0.0512(4) Uani 1 1 d . . . . .
H24 H 0.3026 0.3261 0.6236 0.061 Uiso 1 1 calc R U . . .
C25 C 0.35690(16) 0.47566(16) 0.58320(6) 0.0513(4) Uani 1 1 d . . . . .
H25 H 0.2870 0.4749 0.5581 0.062 Uiso 1 1 calc R U . . .
C26 C 0.59163(15) 0.25112(14) 0.72821(6) 0.0451(4) Uani 1 1 d . . . . .
C27 C 0.68940(16) 0.22572(16) 0.70284(6) 0.0535(4) Uani 1 1 d . . . . .
H27 H 0.6793 0.2364 0.6677 0.064 Uiso 1 1 calc R U . . .
C28 C 0.80196(17) 0.18465(18) 0.72921(8) 0.0631(5) Uani 1 1 d . . . . .
H28 H 0.8677 0.1695 0.7118 0.076 Uiso 1 1 calc R U . . .
C29 C 0.81750(19) 0.16599(18) 0.78098(8) 0.0668(5) Uani 1 1 d . . . . .
H29 H 0.8937 0.1391 0.7987 0.080 Uiso 1 1 calc R U . . .
C30 C 0.7198(2) 0.18726(18) 0.80636(7) 0.0655(5) Uani 1 1 d . . . . .
H30 H 0.7296 0.1729 0.8413 0.079 Uiso 1 1 calc R U . . .
C31 C 0.60662(17) 0.22992(16) 0.78040(6) 0.0556(4) Uani 1 1 d . . . . .
H31 H 0.5409 0.2443 0.7979 0.067 Uiso 1 1 calc R U . . .
C32 C 0.36555(15) 0.23989(16) 0.71430(6) 0.0480(4) Uani 1 1 d . . . . .
C33 C 0.34520(16) 0.10619(17) 0.71026(6) 0.0542(4) Uani 1 1 d . . . . .
H33 H 0.4048 0.0517 0.7000 0.065 Uiso 1 1 calc R U . . .
C34 C 0.23747(17) 0.0525(2) 0.72133(7) 0.0673(5) Uani 1 1 d . . . . .
H34 H 0.2246 -0.0380 0.7185 0.081 Uiso 1 1 calc R U . . .
C35 C 0.14980(19) 0.1310(2) 0.73644(9) 0.0829(7) Uani 1 1 d . . . . .
H35 H 0.0771 0.0945 0.7440 0.099 Uiso 1 1 calc R U . . .
C36 C 0.1690(2) 0.2647(3) 0.74053(10) 0.0934(8) Uani 1 1 d . . . . .
H36 H 0.1086 0.3186 0.7505 0.112 Uiso 1 1 calc R U . . .
C37 C 0.2774(2) 0.3198(2) 0.72990(8) 0.0747(6) Uani 1 1 d . . . . .
H37 H 0.2906 0.4103 0.7333 0.090 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 C9 1.324(2) . ?
N1 C1 1.356(2) . ?
N2 C12 1.148(2) . ?
N3 C9 1.384(2) . ?
N3 C13 1.463(2) . ?
N3 C17 1.463(2) . ?
N4 C23 1.4042(19) . ?
N4 C26 1.420(2) . ?
N4 C32 1.429(2) . ?
C1 C2 1.356(3) . ?
C1 C10 1.505(3) . ?
C2 C3 1.411(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(2) . ?
C3 C8 1.421(2) . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.419(2) . ?
C5 C11 1.505(2) . ?
C6 C7 1.395(2) . ?
C6 C12 1.436(2) . ?
C7 C18 1.426(2) . ?
C7 C8 1.428(2) . ?
C8 C9 1.444(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.521(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.517(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.510(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.516(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.198(2) . ?
C19 C20 1.425(2) . ?
C20 C25 1.389(2) . ?
C20 C21 1.396(2) . ?
C21 C22 1.374(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.395(2) . ?
C24 C25 1.374(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.380(2) . ?
C26 C31 1.388(2) . ?
C27 C28 1.380(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.373(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.386(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.375(2) . ?
C32 C37 1.376(2) . ?
C33 C34 1.374(2) . ?
C33 H33 0.9300 . ?
C34 C35 1.358(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.373(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.382(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 119.45(16) . . ?
C9 N3 C13 118.72(13) . . ?
C9 N3 C17 118.24(14) . . ?
C13 N3 C17 112.52(13) . . ?
C23 N4 C26 121.87(13) . . ?
C23 N4 C32 119.55(13) . . ?
C26 N4 C32 118.40(12) . . ?
C2 C1 N1 122.26(17) . . ?
C2 C1 C10 122.86(19) . . ?
N1 C1 C10 114.9(2) . . ?
C1 C2 C3 120.01(16) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 121.93(16) . . ?
C2 C3 C8 118.24(17) . . ?
C4 C3 C8 119.64(15) . . ?
C5 C4 C3 122.88(15) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 117.32(16) . . ?
C4 C5 C11 122.08(17) . . ?
C6 C5 C11 120.53(17) . . ?
C7 C6 C5 122.53(15) . . ?
C7 C6 C12 118.68(14) . . ?
C5 C6 C12 118.79(15) . . ?
C6 C7 C18 116.92(14) . . ?
C6 C7 C8 119.18(14) . . ?
C18 C7 C8 123.76(14) . . ?
C3 C8 C7 118.09(15) . . ?
C3 C8 C9 116.25(14) . . ?
C7 C8 C9 125.41(14) . . ?
N1 C9 N3 117.31(15) . . ?
N1 C9 C8 122.09(15) . . ?
N3 C9 C8 120.53(14) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 178.21(19) . . ?
N3 C13 C14 111.73(14) . . ?
N3 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 111.49(16) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 110.17(17) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C17 110.68(18) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N3 C17 C16 113.59(15) . . ?
N3 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
N3 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C7 171.51(17) . . ?
C18 C19 C20 179.43(19) . . ?
C25 C20 C21 117.71(14) . . ?
C25 C20 C19 121.98(14) . . ?
C21 C20 C19 120.30(14) . . ?
C22 C21 C20 121.09(15) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 121.01(15) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C24 118.04(14) . . ?
C22 C23 N4 121.58(14) . . ?
C24 C23 N4 120.38(14) . . ?
C25 C24 C23 120.76(15) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C20 121.37(15) . . ?
C24 C25 H25 119.3 . . ?
C20 C25 H25 119.3 . . ?
C27 C26 C31 119.04(16) . . ?
C27 C26 N4 121.16(14) . . ?
C31 C26 N4 119.80(15) . . ?
C28 C27 C26 120.56(16) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 120.39(18) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 119.51(18) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C30 C31 120.66(17) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C30 C31 C26 119.80(18) . . ?
C30 C31 H31 120.1 . . ?
C26 C31 H31 120.1 . . ?
C33 C32 C37 119.43(17) . . ?
C33 C32 N4 120.64(15) . . ?
C37 C32 N4 119.92(16) . . ?
C34 C33 C32 120.50(17) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 120.32(19) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 119.7(2) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C35 C36 C37 120.6(2) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C32 C37 C36 119.5(2) . . ?
C32 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 3.8(3) . . . . ?
C9 N1 C1 C10 -176.09(17) . . . . ?
N1 C1 C2 C3 -10.7(3) . . . . ?
C10 C1 C2 C3 169.24(19) . . . . ?
C1 C2 C3 C4 -170.12(16) . . . . ?
C1 C2 C3 C8 4.8(2) . . . . ?
C2 C3 C4 C5 171.11(16) . . . . ?
C8 C3 C4 C5 -3.8(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C3 C4 C5 C11 -177.43(16) . . . . ?
C4 C5 C6 C7 1.5(2) . . . . ?
C11 C5 C6 C7 178.43(15) . . . . ?
C4 C5 C6 C12 -178.45(15) . . . . ?
C11 C5 C6 C12 -1.6(2) . . . . ?
C5 C6 C7 C18 -173.96(14) . . . . ?
C12 C6 C7 C18 6.0(2) . . . . ?
C5 C6 C7 C8 1.9(2) . . . . ?
C12 C6 C7 C8 -178.13(13) . . . . ?
C2 C3 C8 C7 -168.03(14) . . . . ?
C4 C3 C8 C7 7.0(2) . . . . ?
C2 C3 C8 C9 6.6(2) . . . . ?
C4 C3 C8 C9 -178.36(14) . . . . ?
C6 C7 C8 C3 -6.1(2) . . . . ?
C18 C7 C8 C3 169.43(14) . . . . ?
C6 C7 C8 C9 179.83(14) . . . . ?
C18 C7 C8 C9 -4.6(2) . . . . ?
C1 N1 C9 N3 -174.33(15) . . . . ?
C1 N1 C9 C8 8.7(2) . . . . ?
C13 N3 C9 N1 124.21(16) . . . . ?
C17 N3 C9 N1 -18.0(2) . . . . ?
C13 N3 C9 C8 -58.77(19) . . . . ?
C17 N3 C9 C8 159.05(14) . . . . ?
C3 C8 C9 N1 -13.7(2) . . . . ?
C7 C8 C9 N1 160.47(15) . . . . ?
C3 C8 C9 N3 169.44(13) . . . . ?
C7 C8 C9 N3 -16.4(2) . . . . ?
C9 N3 C13 C14 -90.66(18) . . . . ?
C17 N3 C13 C14 53.56(19) . . . . ?
N3 C13 C14 C15 -54.9(2) . . . . ?
C13 C14 C15 C16 55.1(2) . . . . ?
C14 C15 C16 C17 -53.7(2) . . . . ?
C9 N3 C17 C16 90.8(2) . . . . ?
C13 N3 C17 C16 -53.6(2) . . . . ?
C15 C16 C17 N3 53.6(2) . . . . ?
C25 C20 C21 C22 0.4(2) . . . . ?
C19 C20 C21 C22 -178.82(14) . . . . ?
C20 C21 C22 C23 1.0(2) . . . . ?
C21 C22 C23 C24 -1.4(2) . . . . ?
C21 C22 C23 N4 179.71(15) . . . . ?
C26 N4 C23 C22 -29.4(2) . . . . ?
C32 N4 C23 C22 155.67(15) . . . . ?
C26 N4 C23 C24 151.75(15) . . . . ?
C32 N4 C23 C24 -23.2(2) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
N4 C23 C24 C25 179.34(15) . . . . ?
C23 C24 C25 C20 1.0(3) . . . . ?
C21 C20 C25 C24 -1.4(2) . . . . ?
C19 C20 C25 C24 177.84(15) . . . . ?
C23 N4 C26 C27 -38.1(2) . . . . ?
C32 N4 C26 C27 136.87(16) . . . . ?
C23 N4 C26 C31 142.82(16) . . . . ?
C32 N4 C26 C31 -42.2(2) . . . . ?
C31 C26 C27 C28 -2.4(2) . . . . ?
N4 C26 C27 C28 178.52(15) . . . . ?
C26 C27 C28 C29 1.3(3) . . . . ?
C27 C28 C29 C30 0.6(3) . . . . ?
C28 C29 C30 C31 -1.3(3) . . . . ?
C29 C30 C31 C26 0.1(3) . . . . ?
C27 C26 C31 C30 1.7(2) . . . . ?
N4 C26 C31 C30 -179.22(15) . . . . ?
C23 N4 C32 C33 117.24(17) . . . . ?
C26 N4 C32 C33 -57.9(2) . . . . ?
C23 N4 C32 C37 -61.8(2) . . . . ?
C26 N4 C32 C37 123.06(18) . . . . ?
C37 C32 C33 C34 0.5(3) . . . . ?
N4 C32 C33 C34 -178.59(15) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C34 C35 C36 C37 -0.7(4) . . . . ?
C33 C32 C37 C36 -1.0(3) . . . . ?
N4 C32 C37 C36 178.09(19) . . . . ?
C35 C36 C37 C32 1.1(4) . . . . ?

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4

