# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_cd213238
_database_code_depnum_ccdc_archive 'CCDC 949993'
_audit_update_record             
;
2013-07-12 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N6 O'
_chemical_formula_weight         358.40

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                   20.5231(17)
_cell_length_b                   9.5667(8)
_cell_length_c                   20.3255(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.091(2)
_cell_angle_gamma                90.00
_cell_volume                     3614.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1892
_cell_measurement_theta_min      4.426
_cell_measurement_theta_max      42.860

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0893
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19720
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.05
_reflns_number_total             6402
_reflns_number_gt                4107
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0466P)²+4.1895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6402
_refine_ls_number_parameters     497
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.1857
_refine_ls_wR_factor_gt          0.1656
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.42533(14) -0.2229(3) 0.36115(14) 0.0515(7) Uani 1 1 d . . .
O2 O 0.90889(17) 1.1897(3) 0.07508(17) 0.0728(9) Uani 1 1 d . . .
N1 N 0.40953(16) -0.0535(3) 0.43252(16) 0.0466(8) Uani 1 1 d . . .
N2 N 0.3163(2) 0.2464(4) 0.10637(19) 0.0688(10) Uani 1 1 d . . .
N3 N 0.38571(19) 0.2246(4) 0.13919(17) 0.0561(9) Uani 1 1 d . . .
N4 N 0.39600(16) 0.1408(3) 0.19641(15) 0.0416(7) Uani 1 1 d . . .
N5 N 0.47117(15) 0.0282(3) 0.30528(15) 0.0367(7) Uani 1 1 d . . .
N6 N 0.51753(17) 0.1089(4) 0.22653(18) 0.0442(8) Uani 1 1 d . . .
N7 N 0.90661(19) 1.0299(5) -0.00880(19) 0.0682(11) Uani 1 1 d . . .
N8 N 0.8227(2) 0.6876(4) 0.2364(2) 0.0704(11) Uani 1 1 d . . .
N9 N 0.8900(2) 0.7202(4) 0.26250(19) 0.0615(10) Uani 1 1 d . . .
N10 N 0.89752(17) 0.8071(3) 0.21314(16) 0.0502(8) Uani 1 1 d . . .
N11 N 0.96803(16) 0.9343(3) 0.16806(16) 0.0504(8) Uani 1 1 d . . .
N12 N 1.0183(2) 0.8493(4) 0.28577(19) 0.0607(10) Uani 1 1 d . . .
C1 C 0.40646(19) 0.0938(4) 0.43274(19) 0.0458(9) Uani 1 1 d . . .
C2 C 0.4054(2) 0.1800(5) 0.4866(2) 0.0628(12) Uani 1 1 d . . .
H2 H 0.4034 0.1444 0.5283 0.075 Uiso 1 1 calc R . .
C3 C 0.4075(3) 0.3224(6) 0.4755(3) 0.0770(15) Uani 1 1 d . . .
H3 H 0.4064 0.3837 0.5105 0.092 Uiso 1 1 calc R . .
C4 C 0.4110(3) 0.3758(5) 0.4147(3) 0.0730(14) Uani 1 1 d . . .
H4 H 0.4133 0.4721 0.4095 0.088 Uiso 1 1 calc R . .
C5 C 0.4111(2) 0.2872(4) 0.3605(2) 0.0558(11) Uani 1 1 d . . .
H5 H 0.4133 0.3231 0.3189 0.067 Uiso 1 1 calc R . .
C6 C 0.40808(18) 0.1458(4) 0.36971(19) 0.0404(9) Uani 1 1 d . . .
C7 C 0.40928(18) 0.0239(4) 0.32300(18) 0.0376(8) Uani 1 1 d . . .
C8 C 0.41737(18) -0.1021(4) 0.37329(19) 0.0402(8) Uani 1 1 d . . .
C9 C 0.4094(2) -0.1430(5) 0.4908(2) 0.0637(12) Uani 1 1 d . . .
H9A H 0.3616 -0.1477 0.4880 0.096 Uiso 1 1 calc R . .
H9B H 0.4414 -0.1048 0.5369 0.096 Uiso 1 1 calc R . .
H9C H 0.4251 -0.2352 0.4857 0.096 Uiso 1 1 calc R . .
C10 C 0.33615(18) 0.0057(4) 0.25607(19) 0.0435(9) Uani 1 1 d . . .
H10A H 0.3316 -0.0891 0.2377 0.052 Uiso 1 1 calc R . .
H10B H 0.2969 0.0232 0.2697 0.052 Uiso 1 1 calc R . .
C11 C 0.33291(19) 0.1067(4) 0.19908(19) 0.0433(9) Uani 1 1 d . . .
C12 C 0.2832(2) 0.1757(5) 0.1414(2) 0.0603(11) Uani 1 1 d . . .
H12 H 0.2338 0.1747 0.1278 0.072 Uiso 1 1 calc R . .
C13 C 0.46372(18) 0.0894(4) 0.24700(17) 0.0357(8) Uani 1 1 d . . .
C14 C 0.58956(19) 0.0680(4) 0.2740(2) 0.0448(9) Uani 1 1 d . . .
H14A H 0.6170 0.0616 0.2452 0.054 Uiso 1 1 calc R . .
H14B H 0.5876 -0.0251 0.2920 0.054 Uiso 1 1 calc R . .
C15 C 0.6303(2) 0.1600(4) 0.3380(2) 0.0494(10) Uani 1 1 d . . .
C16 C 0.6994(3) 0.1193(6) 0.3854(3) 0.0845(16) Uani 1 1 d . . .
H16 H 0.7186 0.0370 0.3767 0.101 Uiso 1 1 calc R . .
C17 C 0.7393(4) 0.1983(11) 0.4443(4) 0.132(3) Uani 1 1 d . . .
H17 H 0.7852 0.1695 0.4761 0.159 Uiso 1 1 calc R . .
C18 C 0.7120(5) 0.3191(9) 0.4566(4) 0.132(4) Uani 1 1 d . . .
H18 H 0.7396 0.3735 0.4967 0.159 Uiso 1 1 calc R . .
C19 C 0.6439(5) 0.3624(6) 0.4105(3) 0.109(2) Uani 1 1 d . . .
H19 H 0.6257 0.4457 0.4195 0.131 Uiso 1 1 calc R . .
C20 C 0.6022(3) 0.2813(4) 0.3504(2) 0.0668(13) Uani 1 1 d . . .
H20 H 0.5560 0.3093 0.3192 0.080 Uiso 1 1 calc R . .
C21 C 0.9109(2) 0.8863(6) -0.0138(2) 0.0639(13) Uani 1 1 d . . .
C22 C 0.9177(3) 0.8102(9) -0.0663(3) 0.102(2) Uani 1 1 d . . .
H22 H 0.9188 0.8529 -0.1070 0.123 Uiso 1 1 calc R . .
C23 C 0.9230(3) 0.6700(9) -0.0580(4) 0.111(2) Uani 1 1 d . . .
H23 H 0.9259 0.6161 -0.0948 0.133 Uiso 1 1 calc R . .
C24 C 0.9242(3) 0.6022(7) 0.0037(5) 0.115(2) Uani 1 1 d . . .
H24 H 0.9291 0.5055 0.0077 0.138 Uiso 1 1 calc R . .
C25 C 0.9180(2) 0.6800(6) 0.0597(3) 0.0797(15) Uani 1 1 d . . .
H25 H 0.9180 0.6377 0.1009 0.096 Uiso 1 1 calc R . .
C26 C 0.9120(2) 0.8221(5) 0.0495(2) 0.0594(11) Uani 1 1 d . . .
C27 C 0.9057(2) 0.9344(4) 0.09711(19) 0.0493(10) Uani 1 1 d . . .
C28 C 0.9085(2) 1.0694(5) 0.0549(2) 0.0539(11) Uani 1 1 d . . .
C29 C 0.9020(2) 1.1274(7) -0.0670(2) 0.096(2) Uani 1 1 d . . .
H29A H 0.8564 1.1162 -0.1081 0.145 Uiso 1 1 calc R . .
H36B H 0.9400 1.1077 -0.0813 0.145 Uiso 1 1 calc R . .
H29C H 0.9065 1.2218 -0.0495 0.145 Uiso 1 1 calc R . .
C30 C 0.8323(2) 0.9327(5) 0.1009(2) 0.0554(11) Uani 1 1 d . . .
H30A H 0.8218 1.0249 0.1139 0.066 Uiso 1 1 calc R . .
H30B H 0.7947 0.9082 0.0538 0.066 Uiso 1 1 calc R . .
C31 C 0.8338(2) 0.8296(4) 0.1559(2) 0.0517(10) Uani 1 1 d . . .
C32 C 0.7866(2) 0.7519(5) 0.1712(3) 0.0644(12) Uani 1 1 d . . .
H32 H 0.7375 0.7440 0.1418 0.077 Uiso 1 1 calc R . .
C33 C 0.9632(2) 0.8680(4) 0.2197(2) 0.0487(10) Uani 1 1 d . . .
C34 C 1.0907(2) 0.8934(5) 0.3009(2) 0.0612(12) Uani 1 1 d . . .
H34A H 1.1147 0.9202 0.3516 0.073 Uiso 1 1 calc R . .
H34B H 1.0878 0.9760 0.2720 0.073 Uiso 1 1 calc R . .
C35 C 1.1361(2) 0.7870(4) 0.2860(2) 0.0534(10) Uani 1 1 d . . .
C36 C 1.2092(3) 0.7857(5) 0.3273(3) 0.0828(16) Uani 1 1 d . . .
H36 H 1.2294 0.8509 0.3644 0.099 Uiso 1 1 calc R . .
C37 C 1.2530(3) 0.6919(7) 0.3154(4) 0.108(2) Uani 1 1 d . . .
H37 H 1.3022 0.6935 0.3446 0.130 Uiso 1 1 calc R . .
C38 C 1.2250(4) 0.5956(7) 0.2610(4) 0.106(2) Uani 1 1 d . . .
H38 H 1.2548 0.5326 0.2521 0.128 Uiso 1 1 calc R . .
C39 C 1.1546(4) 0.5937(7) 0.2213(3) 0.1024(19) Uani 1 1 d . . .
H39 H 1.1351 0.5276 0.1846 0.123 Uiso 1 1 calc R . .
C40 C 1.1089(3) 0.6882(6) 0.2331(3) 0.0814(15) Uani 1 1 d . . .
H40 H 1.0595 0.6837 0.2046 0.098 Uiso 1 1 calc R . .
H12A H 1.003(3) 0.795(5) 0.314(3) 0.097(18) Uiso 1 1 d . . .
H6A H 0.511(2) 0.169(4) 0.197(2) 0.068(16) Uiso 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
O1 C8 1.207(4) . ?
O2 C28 1.221(5) . ?
N1 C8 1.362(4) . ?
N1 C1 1.411(5) . ?
N1 C9 1.462(5) . ?
N2 N3 1.307(4) . ?
N2 C12 1.356(5) . ?
N3 N4 1.354(4) . ?
N4 C11 1.359(4) . ?
N4 C13 1.421(4) . ?
N5 C13 1.271(4) . ?
N5 C7 1.460(4) . ?
N6 C13 1.348(4) . ?
N6 C14 1.435(5) . ?
N6 H6A 0.79(4) . ?
N7 C28 1.334(5) . ?
N7 C21 1.383(6) . ?
N7 C29 1.478(6) . ?
N8 N9 1.291(5) . ?
N8 C32 1.362(5) . ?
N9 N10 1.361(4) . ?
N10 C31 1.349(5) . ?
N10 C33 1.422(5) . ?
N11 C33 1.265(5) . ?
N11 C27 1.467(4) . ?
N12 C33 1.352(5) . ?
N12 C34 1.447(5) . ?
N12 H12A 0.93(5) . ?
C1 C2 1.378(5) . ?
C1 C6 1.388(5) . ?
C2 C3 1.385(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.511(5) . ?
C7 C8 1.543(5) . ?
C7 C10 1.550(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.488(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.356(5) . ?
C12 H12 0.9300 . ?
C14 C15 1.498(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.366(6) . ?
C15 C16 1.390(6) . ?
C16 C17 1.358(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.354(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.348(7) . ?
C21 C26 1.417(6) . ?
C22 C23 1.351(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.403(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.409(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.487(6) . ?
C27 C30 1.542(5) . ?
C27 C28 1.565(6) . ?
C29 H29A 0.9600 . ?
C29 H36B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.480(5) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.358(6) . ?
C32 H32 0.9300 . ?
C34 C35 1.495(6) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C40 1.361(6) . ?
C35 C36 1.375(6) . ?
C36 C37 1.362(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.365(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.323(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.395(7) . ?
C39 H39 0.9300 . ?
C40 H40 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
C8 N1 C1 111.4(3) . . ?
C8 N1 C9 123.9(3) . . ?
C1 N1 C9 124.5(3) . . ?
N3 N2 C12 109.5(3) . . ?
N2 N3 N4 105.8(3) . . ?
N3 N4 C11 111.9(3) . . ?
N3 N4 C13 125.1(3) . . ?
C11 N4 C13 123.0(3) . . ?
C13 N5 C7 118.0(3) . . ?
C13 N6 C14 120.0(3) . . ?
C13 N6 H6A 115(3) . . ?
C14 N6 H6A 121(3) . . ?
C28 N7 C21 112.0(4) . . ?
C28 N7 C29 124.4(5) . . ?
C21 N7 C29 123.6(4) . . ?
N9 N8 C32 109.7(4) . . ?
N8 N9 N10 106.3(3) . . ?
C31 N10 N9 111.3(3) . . ?
C31 N10 C33 123.3(3) . . ?
N9 N10 C33 125.5(3) . . ?
C33 N11 C27 118.3(3) . . ?
C33 N12 C34 121.5(4) . . ?
C33 N12 H12A 109(3) . . ?
C34 N12 H12A 128(3) . . ?
C2 C1 C6 122.3(4) . . ?
C2 C1 N1 128.0(4) . . ?
C6 C1 N1 109.7(3) . . ?
C1 C2 C3 116.5(4) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 122.2(4) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.5(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 131.5(3) . . ?
C1 C6 C7 108.4(3) . . ?
N5 C7 C6 112.4(3) . . ?
N5 C7 C8 109.0(3) . . ?
C6 C7 C8 102.3(3) . . ?
N5 C7 C10 114.0(3) . . ?
C6 C7 C10 111.7(3) . . ?
C8 C7 C10 106.6(3) . . ?
O1 C8 N1 125.8(3) . . ?
O1 C8 C7 126.7(3) . . ?
N1 C8 C7 107.4(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 108.5(3) . . ?
C11 C10 H10A 110.0 . . ?
C7 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C7 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C12 C11 N4 103.2(4) . . ?
C12 C11 C10 139.3(4) . . ?
N4 C11 C10 117.3(3) . . ?
N2 C12 C11 109.6(4) . . ?
N2 C12 H12 125.2 . . ?
C11 C12 H12 125.2 . . ?
N5 C13 N6 124.1(3) . . ?
N5 C13 N4 121.9(3) . . ?
N6 C13 N4 114.0(3) . . ?
N6 C14 C15 117.4(3) . . ?
N6 C14 H14A 107.9 . . ?
C15 C14 H14A 107.9 . . ?
N6 C14 H14B 107.9 . . ?
C15 C14 H14B 107.9 . . ?
H14A C14 H14B 107.2 . . ?
C20 C15 C16 119.8(4) . . ?
C20 C15 C14 122.4(4) . . ?
C16 C15 C14 117.8(4) . . ?
C17 C16 C15 120.7(6) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.8(7) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.8(6) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 119.9(7) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 119.0(5) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C22 C21 N7 128.7(6) . . ?
C22 C21 C26 121.2(6) . . ?
N7 C21 C26 109.9(4) . . ?
C21 C22 C23 117.8(7) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C22 C23 C24 122.8(6) . . ?
C22 C23 H23 118.6 . . ?
C24 C23 H23 118.6 . . ?
C23 C24 C25 120.3(6) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 115.8(6) . . ?
C26 C25 H25 122.1 . . ?
C24 C25 H25 122.1 . . ?
C25 C26 C21 122.1(5) . . ?
C25 C26 C27 130.2(5) . . ?
C21 C26 C27 107.8(4) . . ?
N11 C27 C26 111.0(3) . . ?
N11 C27 C30 114.4(3) . . ?
C26 C27 C30 112.5(3) . . ?
N11 C27 C28 108.7(3) . . ?
C26 C27 C28 101.9(3) . . ?
C30 C27 C28 107.4(3) . . ?
O2 C28 N7 125.9(4) . . ?
O2 C28 C27 126.2(4) . . ?
N7 C28 C27 107.8(4) . . ?
N7 C29 H29A 109.5 . . ?
N7 C29 H36B 109.5 . . ?
H29A C29 H36B 109.5 . . ?
N7 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H36B C29 H29C 109.5 . . ?
C31 C30 C27 109.7(3) . . ?
C31 C30 H30A 109.7 . . ?
C27 C30 H30A 109.7 . . ?
C31 C30 H30B 109.7 . . ?
C27 C30 H30B 109.7 . . ?
H30A C30 H30B 108.2 . . ?
N10 C31 C32 103.9(4) . . ?
N10 C31 C30 117.4(4) . . ?
C32 C31 C30 138.5(4) . . ?
C31 C32 N8 108.9(4) . . ?
C31 C32 H32 125.6 . . ?
N8 C32 H32 125.6 . . ?
N11 C33 N12 124.3(4) . . ?
N11 C33 N10 122.2(3) . . ?
N12 C33 N10 113.5(4) . . ?
N12 C34 C35 115.5(4) . . ?
N12 C34 H34A 108.4 . . ?
C35 C34 H34A 108.4 . . ?
N12 C34 H34B 108.4 . . ?
C35 C34 H34B 108.4 . . ?
H34A C34 H34B 107.5 . . ?
C40 C35 C36 116.9(5) . . ?
C40 C35 C34 123.4(4) . . ?
C36 C35 C34 119.7(4) . . ?
C37 C36 C35 122.0(5) . . ?
C37 C36 H36 119.0 . . ?
C35 C36 H36 119.0 . . ?
C36 C37 C38 120.4(6) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C39 C38 C37 118.6(6) . . ?
C39 C38 H38 120.7 . . ?
C37 C38 H38 120.7 . . ?
C38 C39 C40 121.8(6) . . ?
C38 C39 H39 119.1 . . ?
C40 C39 H39 119.1 . . ?
C35 C40 C39 120.3(5) . . ?
C35 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?

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
C12 N2 N3 N4 -1.0(4) . . . . ?
N2 N3 N4 C11 1.3(4) . . . . ?
N2 N3 N4 C13 179.4(3) . . . . ?
C32 N8 N9 N10 0.0(5) . . . . ?
N8 N9 N10 C31 0.4(4) . . . . ?
N8 N9 N10 C33 -179.6(4) . . . . ?
C8 N1 C1 C2 -173.5(4) . . . . ?
C9 N1 C1 C2 2.5(6) . . . . ?
C8 N1 C1 C6 3.5(4) . . . . ?
C9 N1 C1 C6 179.6(3) . . . . ?
C6 C1 C2 C3 -1.2(6) . . . . ?
N1 C1 C2 C3 175.5(4) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
C2 C3 C4 C5 1.3(8) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C1 -1.4(6) . . . . ?
C4 C5 C6 C7 -178.2(4) . . . . ?
C2 C1 C6 C5 2.2(6) . . . . ?
N1 C1 C6 C5 -175.1(3) . . . . ?
C2 C1 C6 C7 179.7(3) . . . . ?
N1 C1 C6 C7 2.4(4) . . . . ?
C13 N5 C7 C6 -91.7(4) . . . . ?
C13 N5 C7 C8 155.7(3) . . . . ?
C13 N5 C7 C10 36.8(4) . . . . ?
C5 C6 C7 N5 53.8(5) . . . . ?
C1 C6 C7 N5 -123.3(3) . . . . ?
C5 C6 C7 C8 170.5(4) . . . . ?
C1 C6 C7 C8 -6.6(4) . . . . ?
C5 C6 C7 C10 -75.8(5) . . . . ?
C1 C6 C7 C10 107.1(3) . . . . ?
C1 N1 C8 O1 175.8(3) . . . . ?
C9 N1 C8 O1 -0.3(6) . . . . ?
C1 N1 C8 C7 -7.8(4) . . . . ?
C9 N1 C8 C7 176.2(3) . . . . ?
N5 C7 C8 O1 -55.9(5) . . . . ?
C6 C7 C8 O1 -175.0(3) . . . . ?
C10 C7 C8 O1 67.6(4) . . . . ?
N5 C7 C8 N1 127.7(3) . . . . ?
C6 C7 C8 N1 8.6(3) . . . . ?
C10 C7 C8 N1 -108.8(3) . . . . ?
N5 C7 C10 C11 -47.7(4) . . . . ?
C6 C7 C10 C11 81.1(3) . . . . ?
C8 C7 C10 C11 -168.0(3) . . . . ?
N3 N4 C11 C12 -1.1(4) . . . . ?
C13 N4 C11 C12 -179.2(3) . . . . ?
N3 N4 C11 C10 175.3(3) . . . . ?
C13 N4 C11 C10 -2.8(5) . . . . ?
C7 C10 C11 C12 -154.4(5) . . . . ?
C7 C10 C11 N4 31.0(4) . . . . ?
N3 N2 C12 C11 0.4(5) . . . . ?
N4 C11 C12 N2 0.4(4) . . . . ?
C10 C11 C12 N2 -174.6(4) . . . . ?
C7 N5 C13 N6 175.5(3) . . . . ?
C7 N5 C13 N4 -6.0(5) . . . . ?
C14 N6 C13 N5 -4.4(5) . . . . ?
C14 N6 C13 N4 177.1(3) . . . . ?
N3 N4 C13 N5 169.6(3) . . . . ?
C11 N4 C13 N5 -12.6(5) . . . . ?
N3 N4 C13 N6 -11.8(5) . . . . ?
C11 N4 C13 N6 166.0(3) . . . . ?
C13 N6 C14 C15 -75.7(4) . . . . ?
N6 C14 C15 C20 -2.5(5) . . . . ?
N6 C14 C15 C16 178.3(4) . . . . ?
C20 C15 C16 C17 0.5(7) . . . . ?
C14 C15 C16 C17 179.7(5) . . . . ?
C15 C16 C17 C18 -0.9(10) . . . . ?
C16 C17 C18 C19 0.6(11) . . . . ?
C17 C18 C19 C20 0.1(10) . . . . ?
C16 C15 C20 C19 0.3(6) . . . . ?
C14 C15 C20 C19 -178.9(4) . . . . ?
C18 C19 C20 C15 -0.6(8) . . . . ?
C28 N7 C21 C22 -172.8(4) . . . . ?
C29 N7 C21 C22 6.1(7) . . . . ?
C28 N7 C21 C26 3.3(5) . . . . ?
C29 N7 C21 C26 -177.9(4) . . . . ?
N7 C21 C22 C23 178.1(5) . . . . ?
C26 C21 C22 C23 2.5(8) . . . . ?
C21 C22 C23 C24 -2.4(10) . . . . ?
C22 C23 C24 C25 1.6(10) . . . . ?
C23 C24 C25 C26 -0.9(8) . . . . ?
C24 C25 C26 C21 1.0(7) . . . . ?
C24 C25 C26 C27 -179.1(4) . . . . ?
C22 C21 C26 C25 -1.9(7) . . . . ?
N7 C21 C26 C25 -178.2(4) . . . . ?
C22 C21 C26 C27 178.2(4) . . . . ?
N7 C21 C26 C27 1.8(5) . . . . ?
C33 N11 C27 C26 -94.6(4) . . . . ?
C33 N11 C27 C30 34.0(5) . . . . ?
C33 N11 C27 C28 154.1(4) . . . . ?
C25 C26 C27 N11 59.3(6) . . . . ?
C21 C26 C27 N11 -120.8(4) . . . . ?
C25 C26 C27 C30 -70.4(6) . . . . ?
C21 C26 C27 C30 109.5(4) . . . . ?
C25 C26 C27 C28 174.8(4) . . . . ?
C21 C26 C27 C28 -5.2(4) . . . . ?
C21 N7 C28 O2 176.5(4) . . . . ?
C29 N7 C28 O2 -2.4(7) . . . . ?
C21 N7 C28 C27 -6.6(5) . . . . ?
C29 N7 C28 C27 174.5(3) . . . . ?
N11 C27 C28 O2 -58.6(5) . . . . ?
C26 C27 C28 O2 -175.9(4) . . . . ?
C30 C27 C28 O2 65.7(5) . . . . ?
N11 C27 C28 N7 124.5(3) . . . . ?
C26 C27 C28 N7 7.2(4) . . . . ?
C30 C27 C28 N7 -111.2(4) . . . . ?
N11 C27 C30 C31 -44.5(5) . . . . ?
C26 C27 C30 C31 83.4(4) . . . . ?
C28 C27 C30 C31 -165.2(3) . . . . ?
N9 N10 C31 C32 -0.7(4) . . . . ?
C33 N10 C31 C32 179.4(4) . . . . ?
N9 N10 C31 C30 174.4(3) . . . . ?
C33 N10 C31 C30 -5.6(6) . . . . ?
C27 C30 C31 N10 30.6(5) . . . . ?
C27 C30 C31 C32 -156.7(5) . . . . ?
N10 C31 C32 N8 0.7(5) . . . . ?
C30 C31 C32 N8 -172.7(5) . . . . ?
N9 N8 C32 C31 -0.4(5) . . . . ?
C27 N11 C33 N12 174.0(4) . . . . ?
C27 N11 C33 N10 -6.9(6) . . . . ?
C34 N12 C33 N11 -6.1(6) . . . . ?
C34 N12 C33 N10 174.7(3) . . . . ?
C31 N10 C33 N11 -8.7(6) . . . . ?
N9 N10 C33 N11 171.4(4) . . . . ?
C31 N10 C33 N12 170.4(4) . . . . ?
N9 N10 C33 N12 -9.5(5) . . . . ?
C33 N12 C34 C35 -89.6(5) . . . . ?
N12 C34 C35 C40 30.8(6) . . . . ?
N12 C34 C35 C36 -148.9(4) . . . . ?
C40 C35 C36 C37 1.0(8) . . . . ?
C34 C35 C36 C37 -179.3(5) . . . . ?
C35 C36 C37 C38 0.5(9) . . . . ?
C36 C37 C38 C39 -1.4(10) . . . . ?
C37 C38 C39 C40 0.8(10) . . . . ?
C36 C35 C40 C39 -1.6(7) . . . . ?
C34 C35 C40 C39 178.8(5) . . . . ?
C38 C39 C40 C35 0.7(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A N3 0.79(4) 2.38(4) 2.761(5) 110(4) .
N6 H6A O1 0.79(4) 2.36(4) 2.986(4) 137(4) 2_655
N12 H12A O2 0.93(5) 2.42(5) 2.996(5) 120(4) 2_745
N12 H12A N9 0.93(5) 2.22(5) 2.761(6) 116(4) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
