# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_Y
_database_code_depnum_ccdc_archive 'CCDC 1955922'
loop_
_audit_author_name
_audit_author_address
ethenoadenine
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2019-09-26 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H34 N10 O4'
_chemical_formula_weight         766.81

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'

_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                   20.554(2)
_cell_length_b                   7.7056(8)
_cell_length_c                   23.283(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3687.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3548
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      25.39

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17676
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.982
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6451
_reflns_number_gt                4559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0870P)²+0.4818P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1670 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6451
_refine_ls_number_parameters     523
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1730
_refine_ls_wR_factor_gt          0.1531
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002

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
C1 C 0.7407(6) 0.2644(14) 0.6648(7) 0.089(4) Uani 1 1 d . . . . .
H1A H 0.767216 0.228148 0.696620 0.133 Uiso 1 1 calc R U . . .
H1B H 0.716066 0.365038 0.675598 0.133 Uiso 1 1 calc R U . . .
H1C H 0.711587 0.172275 0.654432 0.133 Uiso 1 1 calc R U . . .
C2 C 0.7506(4) 0.3587(12) 0.5691(4) 0.057(2) Uani 1 1 d . . . . .
C3 C 0.6846(3) 0.3564(9) 0.5589(3) 0.0430(18) Uani 1 1 d . . . . .
H3A H 0.656174 0.318758 0.587409 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6604(3) 0.4104(9) 0.5061(3) 0.0392(17) Uani 1 1 d . . . . .
C5 C 0.7023(4) 0.4768(12) 0.4650(4) 0.060(2) Uani 1 1 d . . . . .
H5A H 0.686048 0.521228 0.430732 0.072 Uiso 1 1 calc R U . . .
C6 C 0.7683(4) 0.4764(16) 0.4755(4) 0.085(3) Uani 1 1 d . . . . .
H6A H 0.796912 0.515545 0.447402 0.102 Uiso 1 1 calc R U . . .
C7 C 0.7921(4) 0.4180(16) 0.5274(4) 0.087(3) Uani 1 1 d . . . . .
H7A H 0.836644 0.419021 0.534207 0.104 Uiso 1 1 calc R U . . .
C8 C 0.5887(3) 0.4060(9) 0.4973(3) 0.0402(17) Uani 1 1 d . . . . .
C9 C 0.5654(3) 0.3520(9) 0.4416(3) 0.0365(17) Uani 1 1 d . . . . .
C10 C 0.4980(4) 0.2970(9) 0.3675(3) 0.0339(18) Uani 1 1 d . . . . .
C11 C 0.5955(5) 0.2811(10) 0.3949(4) 0.045(2) Uani 1 1 d . . . . .
H11A H 0.639854 0.257472 0.394077 0.054 Uiso 1 1 calc R U . . .
C12 C 0.4445(3) 0.4142(9) 0.4532(3) 0.0373(17) Uani 1 1 d . . . . .
H12A H 0.448719 0.449583 0.491222 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4379(3) 0.3072(9) 0.3417(3) 0.0327(16) Uani 1 1 d . . . . .
C14 C 0.3860(3) 0.3654(8) 0.3736(3) 0.0324(16) Uani 1 1 d . . . . .
C15 C 0.3561(4) 0.3178(7) 0.2848(3) 0.0362(17) Uani 1 1 d . . . . .
H15A H 0.330703 0.315830 0.251763 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2676(3) 0.4308(8) 0.3510(3) 0.0371(17) Uani 1 1 d . . . . .
H16A H 0.259494 0.417679 0.391803 0.045 Uiso 1 1 calc R U . . .
H16B H 0.236135 0.360112 0.330616 0.045 Uiso 1 1 calc R U . . .
C17 C 0.3069(5) 0.7383(8) 0.3399(5) 0.052(3) Uani 1 1 d . . . . .
H17A H 0.347195 0.705713 0.354575 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2967(5) 0.9077(9) 0.3236(4) 0.073(3) Uani 1 1 d . . . . .
H18A H 0.330805 0.986833 0.325746 0.088 Uiso 1 1 calc R U . . .
C19 C 0.2377(5) 0.9611(9) 0.3045(3) 0.060(3) Uani 1 1 d . . . . .
H19A H 0.230578 1.075502 0.293448 0.072 Uiso 1 1 calc R U . . .
C20 C 0.1895(5) 0.8416(11) 0.3023(4) 0.053(2) Uani 1 1 d . . . . .
H20A H 0.148206 0.878002 0.291154 0.064 Uiso 1 1 calc R U . . .
C21 C 0.1980(4) 0.6730(9) 0.3152(3) 0.038(2) Uani 1 1 d . . . . .
H21A H 0.163826 0.595012 0.310987 0.046 Uiso 1 1 calc R U . . .
C22 C 0.2581(3) 0.6160(8) 0.3348(3) 0.0329(16) Uani 1 1 d . . . . .
C23 C 0.0162(6) 0.7554(12) 0.3368(4) 0.069(3) Uani 1 1 d . . . . .
H23A H -0.008528 0.799237 0.304946 0.103 Uiso 1 1 calc R U . . .
H23B H 0.046888 0.841597 0.349033 0.103 Uiso 1 1 calc R U . . .
H23C H 0.038976 0.652405 0.325279 0.103 Uiso 1 1 calc R U . . .
C24 C -0.0002(4) 0.6503(11) 0.4327(4) 0.055(2) Uani 1 1 d . . . . .
C25 C -0.0434(4) 0.5937(15) 0.4741(5) 0.082(3) Uani 1 1 d . . . . .
H25A H -0.087936 0.598019 0.467192 0.099 Uiso 1 1 calc R U . . .
C26 C -0.0205(4) 0.5311(15) 0.5255(5) 0.083(3) Uani 1 1 d . . . . .
H26A H -0.049705 0.491862 0.553085 0.100 Uiso 1 1 calc R U . . .
C27 C 0.0461(4) 0.5257(12) 0.5368(4) 0.052(2) Uani 1 1 d . . . . .
H27A H 0.061529 0.481188 0.571296 0.063 Uiso 1 1 calc R U . . .
C28 C 0.0884(3) 0.5872(9) 0.4961(3) 0.0393(17) Uani 1 1 d . . . . .
C29 C 0.0662(3) 0.6475(10) 0.4437(3) 0.0441(19) Uani 1 1 d . . . . .
H29A H 0.095556 0.685795 0.416090 0.053 Uiso 1 1 calc R U . . .
C30 C 0.1610(3) 0.5901(9) 0.5055(3) 0.0405(17) Uani 1 1 d . . . . .
C31 C 0.1844(3) 0.6442(9) 0.5611(3) 0.0385(17) Uani 1 1 d . . . . .
C32 C 0.1514(5) 0.7210(9) 0.6062(4) 0.042(2) Uani 1 1 d . . . . .
H32A H 0.107034 0.744922 0.605676 0.050 Uiso 1 1 calc R U . . .
C33 C 0.2507(4) 0.7086(9) 0.6339(3) 0.0337(18) Uani 1 1 d . . . . .
C34 C 0.3128(3) 0.7087(8) 0.6608(3) 0.0297(16) Uani 1 1 d . . . . .
C35 C 0.3641(3) 0.6426(7) 0.6278(3) 0.0296(15) Uani 1 1 d . . . . .
C36 C 0.3051(3) 0.5816(9) 0.5503(3) 0.0410(18) Uani 1 1 d . . . . .
H36A H 0.300885 0.539743 0.513013 0.049 Uiso 1 1 calc R U . . .
C37 C 0.3947(4) 0.7178(7) 0.7140(3) 0.0301(16) Uani 1 1 d . . . . .
H37A H 0.421939 0.737914 0.745239 0.036 Uiso 1 1 calc R U . . .
C38 C 0.4824(3) 0.5861(8) 0.6503(3) 0.0371(17) Uani 1 1 d . . . . .
H38A H 0.514093 0.659297 0.669415 0.045 Uiso 1 1 calc R U . . .
H38B H 0.489694 0.595093 0.609296 0.045 Uiso 1 1 calc R U . . .
C39 C 0.4430(5) 0.2806(10) 0.6677(5) 0.055(3) Uani 1 1 d . . . . .
H39A H 0.401230 0.315128 0.657356 0.066 Uiso 1 1 calc R U . . .
C40 C 0.4544(5) 0.1140(11) 0.6815(5) 0.073(3) Uani 1 1 d . . . . .
H40A H 0.420758 0.033733 0.678701 0.087 Uiso 1 1 calc R U . . .
C41 C 0.5142(5) 0.0602(9) 0.6996(4) 0.062(2) Uani 1 1 d . . . . .
H41A H 0.520355 -0.054849 0.710328 0.074 Uiso 1 1 calc R U . . .
C42 C 0.5648(5) 0.1738(13) 0.7020(4) 0.067(3) Uani 1 1 d . . . . .
H42A H 0.605698 0.136773 0.714001 0.080 Uiso 1 1 calc R U . . .
C43 C 0.5546(4) 0.3486(11) 0.6859(4) 0.054(2) Uani 1 1 d . . . . .
H43 H 0.588820 0.427587 0.686957 0.065 Uiso 1 1 calc R U . . .
C44 C 0.4929(3) 0.4013(8) 0.6686(3) 0.0344(17) Uani 1 1 d . . . . .
N1 N 0.5555(4) 0.2476(7) 0.3497(4) 0.039(2) Uani 1 1 d . . . . .
N2 N 0.4996(3) 0.3590(7) 0.4242(2) 0.0340(13) Uani 1 1 d . . . . .
N3 N 0.3866(3) 0.4185(7) 0.4293(2) 0.0376(14) Uani 1 1 d . . . . .
N4 N 0.4188(3) 0.2731(7) 0.2858(3) 0.0346(18) Uani 1 1 d . . . . .
N5 N 0.3330(3) 0.3674(6) 0.3381(2) 0.0303(12) Uani 1 1 d . . . . .
N6 N 0.1907(4) 0.7571(7) 0.6508(3) 0.041(2) Uani 1 1 d . . . . .
N7 N 0.2500(2) 0.6384(7) 0.5781(2) 0.0319(13) Uani 1 1 d . . . . .
N8 N 0.3628(3) 0.5835(6) 0.5734(2) 0.0346(13) Uani 1 1 d . . . . .
N9 N 0.3329(4) 0.7519(6) 0.7155(3) 0.0354(18) Uani 1 1 d . . . . .
N10 N 0.4171(3) 0.6503(6) 0.6635(2) 0.0309(12) Uani 1 1 d . . . . .
O1 O 0.7789(4) 0.3030(11) 0.6200(4) 0.085(2) Uani 1 1 d . . . . .
O2 O 0.5512(3) 0.4439(8) 0.5369(2) 0.0584(17) Uani 1 1 d . . . . .
O3 O -0.0278(3) 0.7141(10) 0.3842(4) 0.075(2) Uani 1 1 d . . . . .
O4 O 0.1978(3) 0.5485(7) 0.4663(2) 0.0574(17) 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
C1 O1 1.338(15) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.370(12) . ?
C2 C3 1.378(10) . ?
C2 O1 1.388(11) . ?
C3 C4 1.392(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(11) . ?
C4 C8 1.487(9) . ?
C5 C6 1.379(11) . ?
C5 H5A 0.9300 . ?
C6 C7 1.380(13) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 O2 1.237(8) . ?
C8 C9 1.444(9) . ?
C9 C11 1.365(11) . ?
C9 N2 1.414(8) . ?
C10 N1 1.308(10) . ?
C10 C13 1.377(10) . ?
C10 N2 1.403(9) . ?
C11 N1 1.361(12) . ?
C11 H11A 0.9300 . ?
C12 N3 1.315(8) . ?
C12 N2 1.385(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(9) . ?
C13 N4 1.385(10) . ?
C14 N3 1.360(8) . ?
C14 N5 1.367(8) . ?
C15 N4 1.333(9) . ?
C15 N5 1.382(8) . ?
C15 H15A 0.9300 . ?
C16 N5 1.461(8) . ?
C16 C22 1.489(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.375(10) . ?
C17 C22 1.383(11) . ?
C17 H17A 0.9300 . ?
C18 C19 1.356(12) . ?
C18 H18A 0.9300 . ?
C19 C20 1.354(12) . ?
C19 H19A 0.9300 . ?
C20 C21 1.345(11) . ?
C20 H20A 0.9300 . ?
C21 C22 1.388(10) . ?
C21 H21A 0.9300 . ?
C23 O3 1.463(14) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O3 1.355(11) . ?
C24 C25 1.381(12) . ?
C24 C29 1.391(10) . ?
C25 C26 1.374(14) . ?
C25 H25A 0.9300 . ?
C26 C27 1.394(11) . ?
C26 H26A 0.9300 . ?
C27 C28 1.370(11) . ?
C27 H27A 0.9300 . ?
C28 C29 1.382(10) . ?
C28 C30 1.509(9) . ?
C29 H29A 0.9300 . ?
C30 O4 1.228(8) . ?
C30 C31 1.442(9) . ?
C31 C32 1.382(11) . ?
C31 N7 1.405(8) . ?
C32 N6 1.346(12) . ?
C32 H32A 0.9300 . ?
C33 N6 1.346(10) . ?
C33 N7 1.409(9) . ?
C33 C34 1.421(10) . ?
C34 N9 1.381(10) . ?
C34 C35 1.400(9) . ?
C35 N8 1.345(8) . ?
C35 N10 1.372(8) . ?
C36 N8 1.303(8) . ?
C36 N7 1.376(8) . ?
C36 H36A 0.9300 . ?
C37 N9 1.299(9) . ?
C37 N10 1.367(8) . ?
C37 H37A 0.9300 . ?
C38 N10 1.462(8) . ?
C38 C44 1.502(9) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.344(11) . ?
C39 C44 1.385(11) . ?
C39 H39A 0.9300 . ?
C40 C41 1.363(12) . ?
C40 H40A 0.9300 . ?
C41 C42 1.362(12) . ?
C41 H41A 0.9300 . ?
C42 C43 1.413(12) . ?
C42 H42A 0.9300 . ?
C43 C44 1.392(10) . ?
C43 H43 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 119.6(7) . . ?
C7 C2 O1 116.6(8) . . ?
C3 C2 O1 123.7(8) . . ?
C2 C3 C4 120.0(7) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 119.9(7) . . ?
C3 C4 C8 117.9(6) . . ?
C5 C4 C8 122.0(7) . . ?
C6 C5 C4 119.3(9) . . ?
C6 C5 H5A 120.4 . . ?
C4 C5 H5A 120.4 . . ?
C5 C6 C7 120.3(9) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.9 . . ?
C2 C7 C6 120.6(8) . . ?
C2 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
O2 C8 C9 122.1(6) . . ?
O2 C8 C4 120.7(6) . . ?
C9 C8 C4 117.2(6) . . ?
C11 C9 N2 102.7(6) . . ?
C11 C9 C8 132.9(7) . . ?
N2 C9 C8 124.4(6) . . ?
N1 C10 C13 133.5(7) . . ?
N1 C10 N2 112.1(7) . . ?
C13 C10 N2 114.3(6) . . ?
N1 C11 C9 114.7(8) . . ?
N1 C11 H11A 122.6 . . ?
C9 C11 H11A 122.6 . . ?
N3 C12 N2 122.8(6) . . ?
N3 C12 H12A 118.6 . . ?
N2 C12 H12A 118.6 . . ?
C14 C13 C10 118.6(6) . . ?
C14 C13 N4 110.5(6) . . ?
C10 C13 N4 130.8(7) . . ?
N3 C14 N5 125.6(6) . . ?
N3 C14 C13 127.3(6) . . ?
N5 C14 C13 107.1(6) . . ?
N4 C15 N5 112.8(7) . . ?
N4 C15 H15A 123.6 . . ?
N5 C15 H15A 123.6 . . ?
N5 C16 C22 112.9(5) . . ?
N5 C16 H16A 109.0 . . ?
C22 C16 H16A 109.0 . . ?
N5 C16 H16B 109.0 . . ?
C22 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C22 120.8(9) . . ?
C18 C17 H17A 119.6 . . ?
C22 C17 H17A 119.6 . . ?
C19 C18 C17 121.0(9) . . ?
C19 C18 H18A 119.5 . . ?
C17 C18 H18A 119.5 . . ?
C18 C19 C20 117.5(7) . . ?
C18 C19 H19A 121.3 . . ?
C20 C19 H19A 121.3 . . ?
C21 C20 C19 123.5(8) . . ?
C21 C20 H20A 118.2 . . ?
C19 C20 H20A 118.2 . . ?
C20 C21 C22 119.7(7) . . ?
C20 C21 H21A 120.1 . . ?
C22 C21 H21A 120.1 . . ?
C17 C22 C21 117.3(7) . . ?
C17 C22 C16 122.4(7) . . ?
C21 C22 C16 120.3(6) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 C25 115.3(8) . . ?
O3 C24 C29 124.8(8) . . ?
C25 C24 C29 119.8(8) . . ?
C26 C25 C24 119.9(9) . . ?
C26 C25 H25A 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C25 C26 C27 120.7(9) . . ?
C25 C26 H26A 119.6 . . ?
C27 C26 H26A 119.6 . . ?
C28 C27 C26 118.9(8) . . ?
C28 C27 H27A 120.6 . . ?
C26 C27 H27A 120.6 . . ?
C27 C28 C29 121.1(7) . . ?
C27 C28 C30 122.2(7) . . ?
C29 C28 C30 116.7(7) . . ?
C28 C29 C24 119.5(7) . . ?
C28 C29 H29A 120.2 . . ?
C24 C29 H29A 120.2 . . ?
O4 C30 C31 122.5(6) . . ?
O4 C30 C28 119.8(6) . . ?
C31 C30 C28 117.7(6) . . ?
C32 C31 N7 105.7(6) . . ?
C32 C31 C30 129.9(7) . . ?
N7 C31 C30 124.2(6) . . ?
N6 C32 C31 112.3(8) . . ?
N6 C32 H32A 123.9 . . ?
C31 C32 H32A 123.9 . . ?
N6 C33 N7 111.5(7) . . ?
N6 C33 C34 134.0(7) . . ?
N7 C33 C34 114.5(6) . . ?
N9 C34 C35 111.7(6) . . ?
N9 C34 C33 132.4(7) . . ?
C35 C34 C33 115.8(6) . . ?
N8 C35 N10 126.9(6) . . ?
N8 C35 C34 128.6(6) . . ?
N10 C35 C34 104.5(6) . . ?
N8 C36 N7 123.5(6) . . ?
N8 C36 H36A 118.3 . . ?
N7 C36 H36A 118.3 . . ?
N9 C37 N10 115.5(7) . . ?
N9 C37 H37A 122.3 . . ?
N10 C37 H37A 122.3 . . ?
N10 C38 C44 113.2(6) . . ?
N10 C38 H38A 108.9 . . ?
C44 C38 H38A 108.9 . . ?
N10 C38 H38B 108.9 . . ?
C44 C38 H38B 108.9 . . ?
H38A C38 H38B 107.7 . . ?
C40 C39 C44 120.5(9) . . ?
C40 C39 H39A 119.7 . . ?
C44 C39 H39A 119.7 . . ?
C39 C40 C41 121.5(9) . . ?
C39 C40 H40A 119.3 . . ?
C41 C40 H40A 119.3 . . ?
C40 C41 C42 120.4(8) . . ?
C40 C41 H41A 119.8 . . ?
C42 C41 H41A 119.8 . . ?
C41 C42 C43 119.2(8) . . ?
C41 C42 H42A 120.4 . . ?
C43 C42 H42A 120.4 . . ?
C44 C43 C42 119.3(8) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C39 C44 C43 119.0(7) . . ?
C39 C44 C38 121.7(7) . . ?
C43 C44 C38 119.4(6) . . ?
C10 N1 C11 104.2(8) . . ?
C12 N2 C10 123.0(6) . . ?
C12 N2 C9 130.8(5) . . ?
C10 N2 C9 106.2(5) . . ?
C12 N3 C14 113.9(6) . . ?
C15 N4 C13 104.0(6) . . ?
C14 N5 C15 105.5(5) . . ?
C14 N5 C16 127.7(6) . . ?
C15 N5 C16 126.4(6) . . ?
C33 N6 C32 105.6(7) . . ?
C36 N7 C31 131.9(5) . . ?
C36 N7 C33 123.2(6) . . ?
C31 N7 C33 104.9(5) . . ?
C36 N8 C35 114.3(6) . . ?
C37 N9 C34 102.6(7) . . ?
C35 N10 C37 105.7(5) . . ?
C35 N10 C38 126.0(6) . . ?
C37 N10 C38 128.1(6) . . ?
C1 O1 C2 119.3(9) . . ?
C24 O3 C23 116.7(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
C7 C2 C3 C4 1.5(13) . . . . ?
O1 C2 C3 C4 -178.3(8) . . . . ?
C2 C3 C4 C5 -4.1(11) . . . . ?
C2 C3 C4 C8 -179.8(7) . . . . ?
C3 C4 C5 C6 4.9(13) . . . . ?
C8 C4 C5 C6 -179.6(8) . . . . ?
C4 C5 C6 C7 -3.1(16) . . . . ?
C3 C2 C7 C6 0.3(17) . . . . ?
O1 C2 C7 C6 -179.9(10) . . . . ?
C5 C6 C7 C2 0.5(18) . . . . ?
C3 C4 C8 O2 37.3(10) . . . . ?
C5 C4 C8 O2 -138.3(8) . . . . ?
C3 C4 C8 C9 -141.3(7) . . . . ?
C5 C4 C8 C9 43.1(10) . . . . ?
O2 C8 C9 C11 -169.0(8) . . . . ?
C4 C8 C9 C11 9.6(12) . . . . ?
O2 C8 C9 N2 8.8(11) . . . . ?
C4 C8 C9 N2 -172.6(6) . . . . ?
N2 C9 C11 N1 1.7(9) . . . . ?
C8 C9 C11 N1 179.8(7) . . . . ?
N1 C10 C13 C14 179.6(8) . . . . ?
N2 C10 C13 C14 -3.7(10) . . . . ?
N1 C10 C13 N4 -2.8(14) . . . . ?
N2 C10 C13 N4 173.9(7) . . . . ?
C10 C13 C14 N3 1.1(11) . . . . ?
N4 C13 C14 N3 -177.0(6) . . . . ?
C10 C13 C14 N5 178.5(6) . . . . ?
N4 C13 C14 N5 0.4(8) . . . . ?
C22 C17 C18 C19 3.0(16) . . . . ?
C17 C18 C19 C20 0.1(14) . . . . ?
C18 C19 C20 C21 -3.3(13) . . . . ?
C19 C20 C21 C22 3.3(12) . . . . ?
C18 C17 C22 C21 -2.9(15) . . . . ?
C18 C17 C22 C16 179.0(8) . . . . ?
C20 C21 C22 C17 -0.1(12) . . . . ?
C20 C21 C22 C16 178.0(7) . . . . ?
N5 C16 C22 C17 -35.8(10) . . . . ?
N5 C16 C22 C21 146.1(7) . . . . ?
O3 C24 C25 C26 -178.2(10) . . . . ?
C29 C24 C25 C26 -1.5(15) . . . . ?
C24 C25 C26 C27 0.8(17) . . . . ?
C25 C26 C27 C28 1.3(15) . . . . ?
C26 C27 C28 C29 -2.6(12) . . . . ?
C26 C27 C28 C30 178.5(8) . . . . ?
C27 C28 C29 C24 1.8(11) . . . . ?
C30 C28 C29 C24 -179.1(6) . . . . ?
O3 C24 C29 C28 176.6(8) . . . . ?
C25 C24 C29 C28 0.2(12) . . . . ?
C27 C28 C30 O4 138.4(7) . . . . ?
C29 C28 C30 O4 -40.6(10) . . . . ?
C27 C28 C30 C31 -42.1(10) . . . . ?
C29 C28 C30 C31 138.9(7) . . . . ?
O4 C30 C31 C32 168.2(8) . . . . ?
C28 C30 C31 C32 -11.2(12) . . . . ?
O4 C30 C31 N7 -6.7(11) . . . . ?
C28 C30 C31 N7 173.9(6) . . . . ?
N7 C31 C32 N6 -2.5(9) . . . . ?
C30 C31 C32 N6 -178.1(7) . . . . ?
N6 C33 C34 N9 3.6(14) . . . . ?
N7 C33 C34 N9 -174.1(7) . . . . ?
N6 C33 C34 C35 178.9(7) . . . . ?
N7 C33 C34 C35 1.1(9) . . . . ?
N9 C34 C35 N8 178.3(6) . . . . ?
C33 C34 C35 N8 2.1(10) . . . . ?
N9 C34 C35 N10 -1.5(7) . . . . ?
C33 C34 C35 N10 -177.7(5) . . . . ?
C44 C39 C40 C41 3.3(17) . . . . ?
C39 C40 C41 C42 -2.5(16) . . . . ?
C40 C41 C42 C43 0.5(14) . . . . ?
C41 C42 C43 C44 0.6(13) . . . . ?
C40 C39 C44 C43 -2.1(15) . . . . ?
C40 C39 C44 C38 176.7(9) . . . . ?
C42 C43 C44 C39 0.1(13) . . . . ?
C42 C43 C44 C38 -178.7(7) . . . . ?
N10 C38 C44 C39 33.0(11) . . . . ?
N10 C38 C44 C43 -148.3(7) . . . . ?
C13 C10 N1 C11 175.6(8) . . . . ?
N2 C10 N1 C11 -1.2(8) . . . . ?
C9 C11 N1 C10 -0.3(9) . . . . ?
N3 C12 N2 C10 -2.5(10) . . . . ?
N3 C12 N2 C9 177.1(6) . . . . ?
N1 C10 N2 C12 -178.1(6) . . . . ?
C13 C10 N2 C12 4.5(10) . . . . ?
N1 C10 N2 C9 2.3(8) . . . . ?
C13 C10 N2 C9 -175.2(6) . . . . ?
C11 C9 N2 C12 178.1(7) . . . . ?
C8 C9 N2 C12 -0.2(11) . . . . ?
C11 C9 N2 C10 -2.2(7) . . . . ?
C8 C9 N2 C10 179.4(7) . . . . ?
N2 C12 N3 C14 -0.5(9) . . . . ?
N5 C14 N3 C12 -175.8(6) . . . . ?
C13 C14 N3 C12 1.2(10) . . . . ?
N5 C15 N4 C13 -4.2(7) . . . . ?
C14 C13 N4 C15 2.3(7) . . . . ?
C10 C13 N4 C15 -175.5(7) . . . . ?
N3 C14 N5 C15 174.7(6) . . . . ?
C13 C14 N5 C15 -2.9(7) . . . . ?
N3 C14 N5 C16 2.2(10) . . . . ?
C13 C14 N5 C16 -175.3(6) . . . . ?
N4 C15 N5 C14 4.6(7) . . . . ?
N4 C15 N5 C16 177.1(5) . . . . ?
C22 C16 N5 C14 92.5(8) . . . . ?
C22 C16 N5 C15 -78.5(8) . . . . ?
N7 C33 N6 C32 -0.7(8) . . . . ?
C34 C33 N6 C32 -178.5(8) . . . . ?
C31 C32 N6 C33 2.0(9) . . . . ?
N8 C36 N7 C31 -178.8(7) . . . . ?
N8 C36 N7 C33 1.7(11) . . . . ?
C32 C31 N7 C36 -177.6(7) . . . . ?
C30 C31 N7 C36 -1.7(11) . . . . ?
C32 C31 N7 C33 1.9(8) . . . . ?
C30 C31 N7 C33 177.8(7) . . . . ?
N6 C33 N7 C36 178.8(6) . . . . ?
C34 C33 N7 C36 -2.9(10) . . . . ?
N6 C33 N7 C31 -0.7(8) . . . . ?
C34 C33 N7 C31 177.5(6) . . . . ?
N7 C36 N8 C35 1.4(9) . . . . ?
N10 C35 N8 C36 176.3(6) . . . . ?
C34 C35 N8 C36 -3.4(9) . . . . ?
N10 C37 N9 C34 -2.0(7) . . . . ?
C35 C34 N9 C37 2.1(7) . . . . ?
C33 C34 N9 C37 177.5(7) . . . . ?
N8 C35 N10 C37 -179.5(6) . . . . ?
C34 C35 N10 C37 0.2(6) . . . . ?
N8 C35 N10 C38 -3.7(9) . . . . ?
C34 C35 N10 C38 176.0(5) . . . . ?
N9 C37 N10 C35 1.2(7) . . . . ?
N9 C37 N10 C38 -174.5(6) . . . . ?
C44 C38 N10 C35 -91.1(7) . . . . ?
C44 C38 N10 C37 83.8(8) . . . . ?
C7 C2 O1 C1 171.6(10) . . . . ?
C3 C2 O1 C1 -8.6(15) . . . . ?
C25 C24 O3 C23 -172.8(8) . . . . ?
C29 C24 O3 C23 10.7(13) . . . . ?

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
C38 H38B O2 0.97 2.41 3.190(9) 137.4 .
C37 H37A N1 0.93 2.48 3.332(10) 152.5 2_665
C36 H36A O4 0.93 2.38 2.957(9) 119.9 .
C16 H16A O4 0.97 2.37 3.177(9) 139.8 .
C15 H15A N6 0.93 2.43 3.299(11) 154.6 4_544
C12 H12A O2 0.93 2.36 2.943(9) 120.4 .
C12 H12A O2 0.93 2.36 2.943(9) 120.4 .
C15 H15A N6 0.93 2.43 3.299(11) 154.6 4_544
C16 H16A O4 0.97 2.37 3.177(9) 139.8 .
C36 H36A O4 0.93 2.38 2.957(9) 119.9 .
C37 H37A N1 0.93 2.48 3.332(10) 152.5 2_665
C38 H38B O2 0.97 2.41 3.190(9) 137.4 .

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.058

