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

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

data_m20160506c1
_database_code_depnum_ccdc_archive 'CCDC 1862113'
_audit_update_record             
;
2018-08-15 deposited with the CCDC.
2018-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   34.80(3)
_cell_length_b                   7.324(6)
_cell_length_c                   12.467(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.174(14)
_cell_angle_gamma                90.00
_cell_volume                     3159(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    1648
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.3

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18364
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5341
_reflns_number_gt                2846
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0898P)²+4.2343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5341
_refine_ls_number_parameters     435
_refine_ls_number_restraints     164
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0802
_refine_ls_wR_factor_ref         0.2635
_refine_ls_wR_factor_gt          0.2096
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36948(11) 0.9052(4) 0.2470(2) 0.0757(10) Uani 1 1 d . . .
O2 O 0.13096(14) 0.1647(4) 0.2655(3) 0.0936(12) Uani 1 1 d . . .
N1 N 0.09113(15) 0.8260(6) 0.8568(4) 0.0932(15) Uani 1 1 d . . .
N2 N 0.22554(13) 0.8913(4) 0.5021(2) 0.0595(11) Uani 1 1 d . . .
N3 N 0.26014(13) 0.8578(4) 0.5392(2) 0.0594(11) Uani 1 1 d . . .
N4 N 0.41153(12) 0.1231(5) -0.3368(3) 0.0706(11) Uani 1 1 d . . .
N5 N 0.27470(12) 0.1352(4) 0.0140(2) 0.0539(9) Uani 1 1 d . . .
N6 N 0.24026(12) 0.1108(4) -0.0253(2) 0.0540(9) Uani 1 1 d . . .
C1 C 0.11342(18) 0.8359(6) 0.7945(4) 0.0753(15) Uani 1 1 d . . .
C2 C 0.14248(17) 0.8469(5) 0.7208(3) 0.0664(14) Uani 1 1 d . . .
C3 C 0.13277(15) 0.9142(5) 0.6165(3) 0.0639(13) Uani 1 1 d . . .
H3A H 0.1070 0.9513 0.5940 0.077 Uiso 1 1 calc R . .
C4 C 0.16080(16) 0.9267(5) 0.5462(3) 0.0628(13) Uani 1 1 d . . .
H4A H 0.1543 0.9716 0.4751 0.075 Uiso 1 1 calc R . .
C5 C 0.19861(15) 0.8733(4) 0.5798(3) 0.0565(12) Uani 1 1 d . . .
C6 C 0.20814(15) 0.8036(4) 0.6842(3) 0.0575(12) Uani 1 1 d . . .
H6A H 0.2338 0.7654 0.7064 0.069 Uiso 1 1 calc R . .
C7 C 0.18036(17) 0.7907(5) 0.7541(3) 0.0663(14) Uani 1 1 d . . .
H7A H 0.1868 0.7438 0.8248 0.080 Uiso 1 1 calc R . .
C8 C 0.28752(15) 0.8734(4) 0.4631(3) 0.0574(13) Uani 1 1 d . . .
C9 C 0.27870(14) 0.9410(4) 0.3574(3) 0.0571(12) Uani 1 1 d . . .
H9A H 0.2532 0.9817 0.3341 0.069 Uiso 1 1 calc R . .
C10 C 0.30660(15) 0.9483(4) 0.2885(3) 0.0615(13) Uani 1 1 d . . .
H10A H 0.3004 0.9920 0.2170 0.074 Uiso 1 1 calc R . .
C11 C 0.34427(16) 0.8919(5) 0.3225(3) 0.0648(14) Uani 1 1 d . . .
C12 C 0.35355(16) 0.8277(5) 0.4274(3) 0.0650(13) Uani 1 1 d . . .
H12A H 0.3792 0.7906 0.4513 0.078 Uiso 1 1 calc R . .
C13 C 0.32507(16) 0.8185(4) 0.4963(3) 0.0643(14) Uani 1 1 d . . .
H13A H 0.3313 0.7738 0.5676 0.077 Uiso 1 1 calc R . .
C14 C 0.40903(18) 0.8551(6) 0.2763(4) 0.0837(16) Uani 1 1 d . B .
H14A H 0.4104 0.7303 0.3069 0.100 Uiso 1 1 calc R . .
H14B H 0.4211 0.9404 0.3315 0.100 Uiso 1 1 calc R . .
C15 C 0.4300(2) 0.8622(6) 0.1777(5) 0.110(2) Uani 1 1 d . . .
H15A H 0.4298 0.9898 0.1514 0.132 Uiso 1 1 calc R A 1
H15B H 0.4157 0.7871 0.1206 0.132 Uiso 1 1 calc R A 1
C16 C 0.47136(19) 0.7964(7) 0.1939(5) 0.1067(18) Uani 0.499(9) 1 d PDU B 1
H16A H 0.4734 0.6763 0.2305 0.128 Uiso 0.499(9) 1 calc PR B 1
H16B H 0.4883 0.8853 0.2360 0.128 Uiso 0.499(9) 1 calc PR B 1
C17 C 0.4814(3) 0.7824(17) 0.0754(8) 0.084(3) Uani 0.499(9) 1 d PDU B 1
H17A H 0.4669 0.6806 0.0377 0.101 Uiso 0.499(9) 1 calc PR B 1
H17B H 0.4743 0.8970 0.0360 0.101 Uiso 0.499(9) 1 calc PR B 1
C18 C 0.5249(3) 0.7485(16) 0.0791(11) 0.094(4) Uani 0.499(9) 1 d PDU B 1
H18A H 0.5321 0.7397 0.0054 0.141 Uiso 0.499(9) 1 calc PR B 1
H18B H 0.5315 0.6342 0.1176 0.141 Uiso 0.499(9) 1 calc PR B 1
H18C H 0.5390 0.8498 0.1167 0.141 Uiso 0.499(9) 1 calc PR B 1
C16' C 0.47136(19) 0.7964(7) 0.1939(5) 0.1067(18) Uani 0.501(9) 1 d P B 2
H16C H 0.4688 0.6645 0.2089 0.128 Uiso 0.501(9) 1 calc PR B 2
H16D H 0.4815 0.8516 0.2637 0.128 Uiso 0.501(9) 1 calc PR B 2
C17' C 0.5061(3) 0.8051(15) 0.1267(8) 0.091(3) Uani 0.501(9) 1 d PDU B 2
H17C H 0.5158 0.9313 0.1204 0.109 Uiso 0.501(9) 1 calc PR B 2
H17D H 0.5275 0.7249 0.1567 0.109 Uiso 0.501(9) 1 calc PR B 2
C18' C 0.4865(4) 0.7333(16) 0.0189(9) 0.092(4) Uani 0.501(9) 1 d PDU B 2
H18D H 0.5053 0.7305 -0.0342 0.138 Uiso 0.501(9) 1 calc PR B 2
H18E H 0.4650 0.8137 -0.0069 0.138 Uiso 0.501(9) 1 calc PR B 2
H18F H 0.4767 0.6096 0.0289 0.138 Uiso 0.501(9) 1 calc PR B 2
C19 C 0.38868(15) 0.1225(5) -0.2761(4) 0.0591(12) Uani 1 1 d . . .
C20 C 0.35949(14) 0.1202(4) -0.2023(3) 0.0556(11) Uani 1 1 d . . .
C21 C 0.36869(15) 0.1745(5) -0.0951(3) 0.0598(12) Uani 1 1 d . . .
H21A H 0.3942 0.2112 -0.0694 0.072 Uiso 1 1 calc R . .
C22 C 0.33967(15) 0.1735(5) -0.0270(3) 0.0590(12) Uani 1 1 d . . .
H22A H 0.3456 0.2088 0.0463 0.071 Uiso 1 1 calc R . .
C23 C 0.30238(13) 0.1225(4) -0.0630(3) 0.0497(11) Uani 1 1 d . . .
C24 C 0.29344(13) 0.0641(4) -0.1697(3) 0.0510(11) Uani 1 1 d . . .
H24A H 0.2680 0.0254 -0.1944 0.061 Uiso 1 1 calc R . .
C25 C 0.32197(13) 0.0633(4) -0.2389(3) 0.0526(11) Uani 1 1 d . . .
H25A H 0.3161 0.0240 -0.3114 0.063 Uiso 1 1 calc R . .
C26 C 0.21263(14) 0.1266(4) 0.0501(3) 0.0515(11) Uani 1 1 d . . .
C27 C 0.17493(15) 0.0817(5) 0.0143(3) 0.0610(12) Uani 1 1 d . . .
H27A H 0.1686 0.0437 -0.0583 0.073 Uiso 1 1 calc R . .
C28 C 0.14597(15) 0.0912(5) 0.0834(4) 0.0675(13) Uani 1 1 d . . .
H28A H 0.1201 0.0586 0.0589 0.081 Uiso 1 1 calc R . .
C29 C 0.15596(19) 0.1498(5) 0.1892(4) 0.0722(15) Uani 1 1 d . . .
C30 C 0.19373(18) 0.1974(5) 0.2255(3) 0.0673(14) Uani 1 1 d . . .
H30A H 0.2002 0.2365 0.2978 0.081 Uiso 1 1 calc R . .
C31 C 0.22144(14) 0.1876(4) 0.1565(3) 0.0556(12) Uani 1 1 d . . .
H31A H 0.2472 0.2227 0.1809 0.067 Uiso 1 1 calc R . .
C32 C 0.0914(2) 0.1451(6) 0.2333(5) 0.101(2) Uani 1 1 d . D .
H32A H 0.0857 0.0215 0.2035 0.121 Uiso 1 1 calc R . .
H32B H 0.0827 0.2366 0.1775 0.121 Uiso 1 1 calc R . .
C33 C 0.0704(2) 0.1764(8) 0.3394(5) 0.117(2) Uani 1 1 d . . .
H33A H 0.0777 0.0775 0.3918 0.140 Uiso 1 1 calc R C 3
H33B H 0.0790 0.2938 0.3732 0.140 Uiso 1 1 calc R C 3
C34 C 0.0298(2) 0.1785(8) 0.3143(6) 0.117(2) Uani 0.706(9) 1 d PDU D 3
H34A H 0.0198 0.0554 0.2940 0.141 Uiso 0.706(9) 1 calc PR D 3
H34B H 0.0219 0.2649 0.2550 0.141 Uiso 0.706(9) 1 calc PR D 3
C35 C 0.0156(2) 0.2430(11) 0.4222(7) 0.097(2) Uani 0.706(9) 1 d PDU D 3
H35A H 0.0271 0.1682 0.4837 0.117 Uiso 0.706(9) 1 calc PR D 3
H35B H 0.0220 0.3730 0.4366 0.117 Uiso 0.706(9) 1 calc PR D 3
C36 C -0.0279(2) 0.2142(12) 0.4016(8) 0.103(3) Uani 0.706(9) 1 d PDU D 3
H36A H -0.0401 0.2529 0.4652 0.155 Uiso 0.706(9) 1 calc PR D 3
H36B H -0.0334 0.0847 0.3875 0.155 Uiso 0.706(9) 1 calc PR D 3
H36C H -0.0383 0.2866 0.3390 0.155 Uiso 0.706(9) 1 calc PR D 3
C34' C 0.0298(2) 0.1785(8) 0.3143(6) 0.117(2) Uani 0.294(9) 1 d P D 4
H34C H 0.0248 0.0752 0.2636 0.141 Uiso 0.294(9) 1 calc PR D 4
H34D H 0.0250 0.2899 0.2699 0.141 Uiso 0.294(9) 1 calc PR D 4
C35' C -0.0052(5) 0.173(3) 0.3837(16) 0.093(4) Uani 0.294(9) 1 d PDU D 4
H35C H -0.0293 0.2089 0.3395 0.112 Uiso 0.294(9) 1 calc PR D 4
H35D H -0.0086 0.0476 0.4116 0.112 Uiso 0.294(9) 1 calc PR D 4
C36' C 0.0039(6) 0.306(2) 0.4768(14) 0.085(5) Uani 0.294(9) 1 d PDU D 4
H36D H -0.0174 0.3060 0.5223 0.127 Uiso 0.294(9) 1 calc PR D 4
H36E H 0.0072 0.4287 0.4481 0.127 Uiso 0.294(9) 1 calc PR D 4
H36F H 0.0278 0.2682 0.5199 0.127 Uiso 0.294(9) 1 calc PR D 4


_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
O1 C11 1.358(5) . ?
O1 C14 1.433(6) . ?
O2 C29 1.361(6) . ?
O2 C32 1.399(7) . ?
N1 C1 1.157(6) . ?
N2 N3 1.267(5) . ?
N2 C5 1.425(6) . ?
N3 C8 1.420(6) . ?
N4 C19 1.155(6) . ?
N5 N6 1.258(5) . ?
N5 C23 1.434(5) . ?
N6 C26 1.420(5) . ?
C1 C2 1.440(7) . ?
C2 C3 1.397(6) . ?
C2 C7 1.401(7) . ?
C3 C4 1.383(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.393(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.403(5) . ?
C6 C7 1.373(6) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C13 1.387(6) . ?
C8 C9 1.410(5) . ?
C9 C10 1.365(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.396(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.395(5) . ?
C12 C13 1.381(6) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.497(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.510(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.558(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.529(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C17' C18' 1.533(9) . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 0.9800 . ?
C19 C20 1.442(7) . ?
C20 C21 1.398(6) . ?
C20 C25 1.400(6) . ?
C21 C22 1.388(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.378(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.401(5) . ?
C24 C25 1.384(6) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 C27 1.380(6) . ?
C26 C31 1.402(5) . ?
C27 C28 1.396(6) . ?
C27 H27A 0.9500 . ?
C28 C29 1.395(6) . ?
C28 H28A 0.9500 . ?
C29 C30 1.388(7) . ?
C30 C31 1.361(6) . ?
C30 H30A 0.9500 . ?
C31 H31A 0.9500 . ?
C32 C33 1.595(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.414(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.555(8) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.524(8) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C35' C36' 1.523(10) . ?
C35' H35C 0.9900 . ?
C35' H35D 0.9900 . ?
C36' H36D 0.9800 . ?
C36' H36E 0.9800 . ?
C36' H36F 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
C11 O1 C14 118.6(4) . . ?
C29 O2 C32 118.3(5) . . ?
N3 N2 C5 113.7(3) . . ?
N2 N3 C8 114.8(3) . . ?
N6 N5 C23 114.3(3) . . ?
N5 N6 C26 114.5(3) . . ?
N1 C1 C2 177.5(6) . . ?
C3 C2 C7 120.4(5) . . ?
C3 C2 C1 119.8(5) . . ?
C7 C2 C1 119.8(4) . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 N2 116.0(3) . . ?
C6 C5 N2 123.8(5) . . ?
C7 C6 C5 120.1(5) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C6 C7 C2 119.7(4) . . ?
C6 C7 H7A 120.1 . . ?
C2 C7 H7A 120.1 . . ?
C13 C8 C9 118.9(4) . . ?
C13 C8 N3 117.1(3) . . ?
C9 C8 N3 123.9(4) . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 120.3(4) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
O1 C11 C12 125.0(5) . . ?
O1 C11 C10 115.0(4) . . ?
C12 C11 C10 120.0(5) . . ?
C13 C12 C11 119.4(5) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C8 121.1(4) . . ?
C12 C13 H13A 119.4 . . ?
C8 C13 H13A 119.4 . . ?
O1 C14 C15 108.8(5) . . ?
O1 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
O1 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C14 C15 C16 114.9(6) . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 C17 101.6(6) . . ?
C15 C16 H16A 111.4 . . ?
C17 C16 H16A 111.4 . . ?
C15 C16 H16B 111.4 . . ?
C17 C16 H16B 111.4 . . ?
H16A C16 H16B 109.3 . . ?
C18 C17 C16 107.7(9) . . ?
C18 C17 H17A 110.2 . . ?
C16 C17 H17A 110.2 . . ?
C18 C17 H17B 110.2 . . ?
C16 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C18' C17' H17C 111.9 . . ?
C18' C17' H17D 111.9 . . ?
H17C C17' H17D 109.6 . . ?
C17' C18' H18D 109.5 . . ?
C17' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C17' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
N4 C19 C20 178.7(5) . . ?
C21 C20 C25 120.4(4) . . ?
C21 C20 C19 120.1(4) . . ?
C25 C20 C19 119.4(4) . . ?
C22 C21 C20 118.5(4) . . ?
C22 C21 H21A 120.8 . . ?
C20 C21 H21A 120.8 . . ?
C23 C22 C21 121.6(4) . . ?
C23 C22 H22A 119.2 . . ?
C21 C22 H22A 119.2 . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 N5 116.2(3) . . ?
C24 C23 N5 124.0(4) . . ?
C25 C24 C23 119.5(4) . . ?
C25 C24 H24A 120.2 . . ?
C23 C24 H24A 120.2 . . ?
C24 C25 C20 120.1(3) . . ?
C24 C25 H25A 119.9 . . ?
C20 C25 H25A 119.9 . . ?
C27 C26 C31 119.1(4) . . ?
C27 C26 N6 117.0(3) . . ?
C31 C26 N6 123.9(4) . . ?
C26 C27 C28 120.9(4) . . ?
C26 C27 H27A 119.6 . . ?
C28 C27 H27A 119.6 . . ?
C29 C28 C27 118.4(5) . . ?
C29 C28 H28A 120.8 . . ?
C27 C28 H28A 120.8 . . ?
O2 C29 C30 113.9(5) . . ?
O2 C29 C28 124.9(6) . . ?
C30 C29 C28 121.1(5) . . ?
C31 C30 C29 119.4(4) . . ?
C31 C30 H30A 120.3 . . ?
C29 C30 H30A 120.3 . . ?
C30 C31 C26 121.1(5) . . ?
C30 C31 H31A 119.4 . . ?
C26 C31 H31A 119.4 . . ?
O2 C32 C33 105.7(5) . . ?
O2 C32 H32A 110.6 . . ?
C33 C32 H32A 110.6 . . ?
O2 C32 H32B 110.6 . . ?
C33 C32 H32B 110.6 . . ?
H32A C32 H32B 108.7 . . ?
C34 C33 C32 110.8(6) . . ?
C34 C33 H33A 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
C33 C34 C35 102.4(6) . . ?
C33 C34 H34A 111.3 . . ?
C35 C34 H34A 111.3 . . ?
C33 C34 H34B 111.3 . . ?
C35 C34 H34B 111.3 . . ?
H34A C34 H34B 109.2 . . ?
C36 C35 C34 102.4(7) . . ?
C36 C35 H35A 111.3 . . ?
C34 C35 H35A 111.3 . . ?
C36 C35 H35B 111.3 . . ?
C34 C35 H35B 111.3 . . ?
H35A C35 H35B 109.2 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C36' C35' H35C 110.3 . . ?
C36' C35' H35D 110.3 . . ?
H35C C35' H35D 108.6 . . ?
C35' C36' H36D 109.5 . . ?
C35' C36' H36E 109.5 . . ?
H36D C36' H36E 109.5 . . ?
C35' C36' H36F 109.5 . . ?
H36D C36' H36F 109.5 . . ?
H36E C36' H36F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 N3 C8 179.5(2) . . . . ?
C23 N5 N6 C26 -178.9(2) . . . . ?
N1 C1 C2 C3 -167(10) . . . . ?
N1 C1 C2 C7 13(10) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C1 C2 C3 C4 179.3(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C3 C4 C5 N2 -179.9(3) . . . . ?
N3 N2 C5 C4 173.6(3) . . . . ?
N3 N2 C5 C6 -7.5(4) . . . . ?
C4 C5 C6 C7 -1.1(5) . . . . ?
N2 C5 C6 C7 -179.9(3) . . . . ?
C5 C6 C7 C2 0.1(5) . . . . ?
C3 C2 C7 C6 0.7(5) . . . . ?
C1 C2 C7 C6 -179.1(3) . . . . ?
N2 N3 C8 C13 -172.9(3) . . . . ?
N2 N3 C8 C9 7.2(5) . . . . ?
C13 C8 C9 C10 1.4(5) . . . . ?
N3 C8 C9 C10 -178.8(3) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?
C14 O1 C11 C12 -1.8(5) . . . . ?
C14 O1 C11 C10 178.2(3) . . . . ?
C9 C10 C11 O1 180.0(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
O1 C11 C12 C13 -179.1(3) . . . . ?
C10 C11 C12 C13 0.8(5) . . . . ?
C11 C12 C13 C8 -0.5(5) . . . . ?
C9 C8 C13 C12 -0.6(5) . . . . ?
N3 C8 C13 C12 179.6(3) . . . . ?
C11 O1 C14 C15 174.1(3) . . . . ?
O1 C14 C15 C16 -174.8(4) . . . . ?
C14 C15 C16 C17 168.6(6) . . . . ?
C15 C16 C17 C18 170.4(8) . . . . ?
N4 C19 C20 C21 -179(100) . . . . ?
N4 C19 C20 C25 1(18) . . . . ?
C25 C20 C21 C22 -1.1(5) . . . . ?
C19 C20 C21 C22 178.9(3) . . . . ?
C20 C21 C22 C23 -0.7(5) . . . . ?
C21 C22 C23 C24 2.2(5) . . . . ?
C21 C22 C23 N5 -177.3(3) . . . . ?
N6 N5 C23 C22 171.1(3) . . . . ?
N6 N5 C23 C24 -8.3(4) . . . . ?
C22 C23 C24 C25 -1.9(5) . . . . ?
N5 C23 C24 C25 177.6(3) . . . . ?
C23 C24 C25 C20 0.1(5) . . . . ?
C21 C20 C25 C24 1.4(5) . . . . ?
C19 C20 C25 C24 -178.6(3) . . . . ?
N5 N6 C26 C27 -173.1(3) . . . . ?
N5 N6 C26 C31 8.1(4) . . . . ?
C31 C26 C27 C28 -1.9(5) . . . . ?
N6 C26 C27 C28 179.3(3) . . . . ?
C26 C27 C28 C29 0.9(5) . . . . ?
C32 O2 C29 C30 171.1(4) . . . . ?
C32 O2 C29 C28 -9.5(6) . . . . ?
C27 C28 C29 O2 -179.5(3) . . . . ?
C27 C28 C29 C30 -0.1(5) . . . . ?
O2 C29 C30 C31 179.8(3) . . . . ?
C28 C29 C30 C31 0.3(6) . . . . ?
C29 C30 C31 C26 -1.4(5) . . . . ?
C27 C26 C31 C30 2.1(5) . . . . ?
N6 C26 C31 C30 -179.1(3) . . . . ?
C29 O2 C32 C33 -178.1(4) . . . . ?
O2 C32 C33 C34 173.9(5) . . . . ?
C32 C33 C34 C35 -170.6(5) . . . . ?
C33 C34 C35 C36 -170.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.044
