# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_cd213323
_audit_block_doi                 10.5517/cc10s0rk
_database_code_depnum_ccdc_archive 'CCDC 946608'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/cplu.201300360 2014
_audit_update_record             
;
2013-06-22 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H26 N14 O15'
_chemical_formula_weight         654.51

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                   11.904(4)
_cell_length_b                   15.824(5)
_cell_length_c                   14.504(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.671(7)
_cell_angle_gamma                90.00
_cell_volume                     2713.6(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4147
_cell_measurement_theta_min      4.922
_cell_measurement_theta_max      45.973

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9707
_exptl_absorpt_correction_T_max  0.9828
_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            15886
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5314
_reflns_number_gt                3954
_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)+(0.0639P)²+0.5866P] 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     SHELXL
_refine_ls_extinction_coef       0.0164(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5314
_refine_ls_number_parameters     481
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

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
N1 N 1.03903(13) 0.23767(10) 0.77937(10) 0.0380(4) Uani 1 1 d . . .
N2 N 1.13784(15) 0.27847(11) 0.82361(13) 0.0481(4) Uani 1 1 d . . .
N3 N 0.88618(14) 0.30903(10) 0.80615(11) 0.0400(4) Uani 1 1 d . . .
N4 N 0.80070(17) 0.33655(12) 0.85266(13) 0.0535(5) Uani 1 1 d . . .
N5 N 0.92167(13) 0.10485(9) 0.73501(10) 0.0367(4) Uani 1 1 d . . .
N6 N 0.92296(15) 0.01611(10) 0.73791(13) 0.0464(4) Uani 1 1 d . . .
N7 N 0.76406(13) 0.17777(10) 0.76333(11) 0.0400(4) Uani 1 1 d . . .
N8 N 0.66516(16) 0.14209(12) 0.78861(14) 0.0544(5) Uani 1 1 d . . .
N9 N 0.96390(13) 0.20723(10) 0.62164(10) 0.0378(4) Uani 1 1 d . . .
N10 N 1.05675(17) 0.17126(12) 0.58352(12) 0.0512(5) Uani 1 1 d . . .
N11 N 0.78862(14) 0.28295(9) 0.65145(11) 0.0407(4) Uani 1 1 d . . .
N12 N 0.70355(15) 0.33048(11) 0.60436(13) 0.0507(5) Uani 1 1 d . . .
N13 N 0.29362(18) 0.09515(12) 0.87858(15) 0.0615(5) Uani 1 1 d . . .
O1 O 1.15312(15) 0.27385(12) 0.90717(12) 0.0674(5) Uani 1 1 d . . .
O2 O 1.20050(14) 0.30868(11) 0.77278(13) 0.0659(5) Uani 1 1 d . . .
O3 O 0.79402(16) 0.30544(12) 0.92894(12) 0.0720(5) Uani 1 1 d . . .
O4 O 0.73940(17) 0.39044(12) 0.81458(14) 0.0800(6) Uani 1 1 d . . .
O5 O 0.90360(15) -0.01700(9) 0.80969(11) 0.0612(4) Uani 1 1 d . . .
O6 O 0.94989(16) -0.01903(9) 0.67013(12) 0.0661(5) Uani 1 1 d . . .
O7 O 0.67307(15) 0.10192(13) 0.85998(13) 0.0758(5) Uani 1 1 d . . .
O8 O 0.57969(14) 0.15919(13) 0.73868(14) 0.0745(5) Uani 1 1 d . . .
O9 O 1.14576(15) 0.20848(13) 0.59791(12) 0.0689(5) Uani 1 1 d . . .
O10 O 1.03733(18) 0.10874(12) 0.53740(14) 0.0801(6) Uani 1 1 d . . .
O11 O 0.71739(15) 0.40592(9) 0.60235(13) 0.0664(5) Uani 1 1 d . . .
O12 O 0.62424(16) 0.29174(12) 0.56687(16) 0.0854(7) Uani 1 1 d . . .
O13 O 0.11369(14) 0.06623(13) 0.90501(12) 0.0694(5) Uani 1 1 d . . .
C1 C 0.94632(17) 0.23138(11) 0.83484(13) 0.0385(4) Uani 1 1 d . . .
H1 H 0.9733 0.2322 0.9013 0.046 Uiso 1 1 calc R . .
C2 C 0.99349(16) 0.27375(11) 0.68845(12) 0.0364(4) Uani 1 1 d . . .
H2 H 1.0482 0.3126 0.6658 0.044 Uiso 1 1 calc R . .
C3 C 0.88360(16) 0.32159(11) 0.70546(13) 0.0371(4) Uani 1 1 d . . .
H3 H 0.8890 0.3817 0.6903 0.045 Uiso 1 1 calc R . .
C4 C 0.87270(16) 0.14962(11) 0.80761(13) 0.0375(4) Uani 1 1 d . . .
H4 H 0.8653 0.1135 0.8615 0.045 Uiso 1 1 calc R . .
C5 C 0.88252(16) 0.14590(11) 0.64623(12) 0.0364(4) Uani 1 1 d . . .
H5 H 0.8659 0.1040 0.5968 0.044 Uiso 1 1 calc R . .
C6 C 0.77305(16) 0.19410(11) 0.66531(13) 0.0374(4) Uani 1 1 d . . .
H6 H 0.7066 0.1729 0.6258 0.045 Uiso 1 1 calc R . .
C7 C 0.2134(2) 0.08241(14) 0.93151(17) 0.0542(6) Uani 1 1 d . . .
C8 C 0.2646(2) 0.08925(18) 1.03116(18) 0.0677(7) Uani 1 1 d . . .
H8A H 0.2262 0.1324 1.0632 0.081 Uiso 1 1 calc R . .
H8B H 0.2584 0.0358 1.0630 0.081 Uiso 1 1 calc R . .
C9 C 0.3831(3) 0.1117(3) 1.0289(3) 0.1031(11) Uani 1 1 d . . .
H9A H 0.4319 0.0733 1.0673 0.124 Uiso 1 1 calc R . .
H9B H 0.3973 0.1689 1.0514 0.124 Uiso 1 1 calc R . .
C10 C 0.4047(2) 0.1046(2) 0.9279(2) 0.0828(9) Uani 1 1 d . . .
H10A H 0.4414 0.1551 0.9080 0.099 Uiso 1 1 calc R . .
H10B H 0.4515 0.0559 0.9185 0.099 Uiso 1 1 calc R . .
C11 C 0.2751(3) 0.0873(2) 0.7783(2) 0.0889(10) Uani 1 1 d . . .
H11A H 0.1965 0.0763 0.7592 0.133 Uiso 1 1 calc R . .
H11B H 0.3197 0.0416 0.7588 0.133 Uiso 1 1 calc R . .
H11C H 0.2967 0.1390 0.7503 0.133 Uiso 1 1 calc R . .
O14 O 0.703(3) 1.0232(19) 0.6305(16) 0.073(3) Uani 0.50 1 d PU A 1
N14 N 0.5819(3) 0.9141(2) 0.6213(3) 0.0508(8) Uani 0.70 1 d PDU A 1
C12 C 0.6556(4) 0.9688(3) 0.5950(4) 0.0423(10) Uani 0.70 1 d PDU A 1
C13 C 0.6758(10) 0.9482(6) 0.4980(7) 0.077(2) Uani 0.70 1 d PDU A 1
H13A H 0.7530 0.9293 0.4957 0.093 Uiso 0.70 1 calc PR A 1
H13B H 0.6618 0.9971 0.4579 0.093 Uiso 0.70 1 calc PR A 1
C14 C 0.5926(4) 0.8780(3) 0.4690(3) 0.0903(14) Uani 0.75 1 d PDU A 1
H14A H 0.6308 0.8311 0.4429 0.108 Uiso 0.75 1 calc PR A 1
H14B H 0.5335 0.8983 0.4226 0.108 Uiso 0.75 1 calc PR A 1
C15 C 0.5437(11) 0.8508(6) 0.5542(7) 0.102(7) Uani 0.65 1 d PDU A 1
H15A H 0.4617 0.8493 0.5436 0.122 Uiso 0.65 1 calc PR A 1
H15B H 0.5713 0.7954 0.5742 0.122 Uiso 0.65 1 calc PR A 1
C16 C 0.5571(9) 0.9085(5) 0.7173(6) 0.079(2) Uani 0.70 1 d PU A 1
H16A H 0.6047 0.9471 0.7551 0.119 Uiso 0.70 1 calc PR A 1
H16B H 0.5709 0.8520 0.7397 0.119 Uiso 0.70 1 calc PR A 1
H16C H 0.4792 0.9229 0.7204 0.119 Uiso 0.70 1 calc PR A 1
O14' O 0.698(3) 1.0274(16) 0.6539(15) 0.063(3) Uani 0.50 1 d PU B 2
N14' N 0.6201(9) 0.9285(7) 0.5540(8) 0.0818(18) Uani 0.30 1 d PDU B 2
C12' C 0.6406(19) 0.9665(14) 0.6331(10) 0.098(8) Uani 0.30 1 d PDU B 2
C13' C 0.564(2) 0.9257(14) 0.6934(19) 0.111(9) Uani 0.30 1 d PDU B 2
H13C H 0.6037 0.9167 0.7547 0.134 Uiso 0.30 1 calc PR B 2
H13D H 0.5000 0.9627 0.6996 0.134 Uiso 0.30 1 calc PR B 2
C14' C 0.5222(16) 0.8450(12) 0.6546(14) 0.150(7) Uani 0.25 1 d PDU B 2
H14C H 0.4418 0.8381 0.6576 0.180 Uiso 0.25 1 calc PR B 2
H14D H 0.5628 0.7976 0.6853 0.180 Uiso 0.25 1 calc PR B 2
C15' C 0.549(2) 0.8556(14) 0.5569(14) 0.113(13) Uani 0.35 1 d PDU B 2
H15G H 0.5871 0.8058 0.5373 0.135 Uiso 0.35 1 calc PR B 2
H15H H 0.4795 0.8633 0.5154 0.135 Uiso 0.35 1 calc PR B 2
C16' C 0.657(2) 0.948(2) 0.4719(19) 0.111(10) Uani 0.30 1 d PDU B 2
H16D H 0.6065 0.9884 0.4394 0.167 Uiso 0.30 1 calc PR B 2
H16E H 0.6602 0.8983 0.4350 0.167 Uiso 0.30 1 calc PR B 2
H16F H 0.7315 0.9727 0.4831 0.167 Uiso 0.30 1 calc PR B 2
O15 O 0.95022(16) 0.10452(11) 0.01990(11) 0.0572(4) Uani 1 1 d D . .
H15C H 1.003(2) 0.089(2) -0.009(2) 0.087(11) Uiso 1 1 d D . .
H15D H 0.932(3) 0.0593(14) 0.0451(19) 0.080(9) Uiso 1 1 d 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 N2 1.427(2) . ?
N1 C1 1.443(3) . ?
N1 C2 1.481(2) . ?
N2 O1 1.207(2) . ?
N2 O2 1.207(2) . ?
N3 N4 1.356(2) . ?
N3 C1 1.458(2) . ?
N3 C3 1.471(2) . ?
N4 O4 1.213(2) . ?
N4 O3 1.222(2) . ?
N5 N6 1.405(2) . ?
N5 C4 1.447(2) . ?
N5 C5 1.469(2) . ?
N6 O6 1.205(2) . ?
N6 O5 1.211(2) . ?
N7 N8 1.393(2) . ?
N7 C4 1.446(2) . ?
N7 C6 1.461(3) . ?
N8 O7 1.209(2) . ?
N8 O8 1.209(2) . ?
N9 N10 1.412(2) . ?
N9 C5 1.445(2) . ?
N9 C2 1.446(2) . ?
N10 O10 1.202(2) . ?
N10 O9 1.209(2) . ?
N11 N12 1.377(2) . ?
N11 C3 1.435(2) . ?
N11 C6 1.435(2) . ?
N12 O12 1.201(2) . ?
N12 O11 1.206(2) . ?
N13 C7 1.309(3) . ?
N13 C10 1.436(4) . ?
N13 C11 1.451(4) . ?
O13 C7 1.231(3) . ?
C1 C4 1.587(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.556(3) . ?
C2 H2 0.9800 . ?
C3 H3 0.9800 . ?
C4 H4 0.9800 . ?
C5 C6 1.562(3) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C7 C8 1.506(4) . ?
C8 C9 1.458(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.520(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O14 C12 1.12(3) . ?
N14 C12 1.319(6) . ?
N14 C15 1.434(7) . ?
N14 C16 1.460(9) . ?
C12 C13 1.492(11) . ?
C13 C14 1.515(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.489(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O14' C12' 1.20(4) . ?
N14' C12' 1.293(16) . ?
N14' C16' 1.36(2) . ?
N14' C15' 1.436(16) . ?
C12' C13' 1.485(18) . ?
C13' C14' 1.458(19) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C14' C15' 1.497(18) . ?
C14' H14C 0.9700 . ?
C14' H14D 0.9700 . ?
C15' H15G 0.9700 . ?
C15' H15H 0.9700 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
O15 H15C 0.829(18) . ?
O15 H15D 0.844(18) . ?

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
N2 N1 C1 115.11(15) . . ?
N2 N1 C2 115.04(15) . . ?
C1 N1 C2 107.38(14) . . ?
O1 N2 O2 127.29(19) . . ?
O1 N2 N1 116.38(18) . . ?
O2 N2 N1 116.12(17) . . ?
N4 N3 C1 120.04(16) . . ?
N4 N3 C3 121.35(16) . . ?
C1 N3 C3 110.49(14) . . ?
O4 N4 O3 126.6(2) . . ?
O4 N4 N3 116.47(19) . . ?
O3 N4 N3 116.90(18) . . ?
N6 N5 C4 118.15(15) . . ?
N6 N5 C5 118.00(14) . . ?
C4 N5 C5 107.92(14) . . ?
O6 N6 O5 126.65(18) . . ?
O6 N6 N5 116.10(17) . . ?
O5 N6 N5 117.09(17) . . ?
N8 N7 C4 119.87(16) . . ?
N8 N7 C6 119.19(16) . . ?
C4 N7 C6 108.90(15) . . ?
O7 N8 O8 127.4(2) . . ?
O7 N8 N7 117.03(19) . . ?
O8 N8 N7 115.45(19) . . ?
N10 N9 C5 113.80(15) . . ?
N10 N9 C2 114.53(15) . . ?
C5 N9 C2 116.20(15) . . ?
O10 N10 O9 127.2(2) . . ?
O10 N10 N9 116.19(19) . . ?
O9 N10 N9 116.50(18) . . ?
N12 N11 C3 121.69(15) . . ?
N12 N11 C6 120.32(16) . . ?
C3 N11 C6 116.56(14) . . ?
O12 N12 O11 126.62(18) . . ?
O12 N12 N11 116.08(17) . . ?
O11 N12 N11 117.25(17) . . ?
C7 N13 C10 114.6(2) . . ?
C7 N13 C11 122.6(3) . . ?
C10 N13 C11 122.2(2) . . ?
N1 C1 N3 99.48(14) . . ?
N1 C1 C4 110.71(15) . . ?
N3 C1 C4 112.17(15) . . ?
N1 C1 H1 111.3 . . ?
N3 C1 H1 111.3 . . ?
C4 C1 H1 111.3 . . ?
N9 C2 N1 110.58(14) . . ?
N9 C2 C3 108.46(14) . . ?
N1 C2 C3 105.90(15) . . ?
N9 C2 H2 110.6 . . ?
N1 C2 H2 110.6 . . ?
C3 C2 H2 110.6 . . ?
N11 C3 N3 114.12(15) . . ?
N11 C3 C2 109.25(15) . . ?
N3 C3 C2 99.84(14) . . ?
N11 C3 H3 111.0 . . ?
N3 C3 H3 111.0 . . ?
C2 C3 H3 111.0 . . ?
N7 C4 N5 104.05(15) . . ?
N7 C4 C1 107.40(14) . . ?
N5 C4 C1 108.84(15) . . ?
N7 C4 H4 112.0 . . ?
N5 C4 H4 112.0 . . ?
C1 C4 H4 112.0 . . ?
N9 C5 N5 111.10(14) . . ?
N9 C5 C6 108.23(14) . . ?
N5 C5 C6 104.29(15) . . ?
N9 C5 H5 111.0 . . ?
N5 C5 H5 111.0 . . ?
C6 C5 H5 111.0 . . ?
N11 C6 N7 109.56(15) . . ?
N11 C6 C5 109.23(15) . . ?
N7 C6 C5 104.06(14) . . ?
N11 C6 H6 111.2 . . ?
N7 C6 H6 111.2 . . ?
C5 C6 H6 111.2 . . ?
O13 C7 N13 126.3(2) . . ?
O13 C7 C8 125.6(2) . . ?
N13 C7 C8 108.1(2) . . ?
C9 C8 C7 106.3(2) . . ?
C9 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 C10 106.0(3) . . ?
C8 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
N13 C10 C9 103.8(2) . . ?
N13 C10 H10A 111.0 . . ?
C9 C10 H10A 111.0 . . ?
N13 C10 H10B 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N13 C11 H11A 109.5 . . ?
N13 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N13 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N14 C15 115.6(5) . . ?
C12 N14 C16 122.0(5) . . ?
C15 N14 C16 121.5(6) . . ?
O14 C12 N14 133.5(12) . . ?
O14 C12 C13 118.1(12) . . ?
N14 C12 C13 108.4(4) . . ?
C12 C13 C14 104.5(5) . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C13 C14 C15 106.7(5) . . ?
C13 C14 H14A 110.4 . . ?
C15 C14 H14A 110.4 . . ?
C13 C14 H14B 110.4 . . ?
C15 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
N14 C15 C14 103.7(5) . . ?
N14 C15 H15A 111.0 . . ?
C14 C15 H15A 111.0 . . ?
N14 C15 H15B 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C12' N14' C16' 128.6(19) . . ?
C12' N14' C15' 113.5(16) . . ?
C16' N14' C15' 117.9(16) . . ?
O14' C12' N14' 130(2) . . ?
O14' C12' C13' 124.9(18) . . ?
N14' C12' C13' 105(2) . . ?
C14' C13' C12' 111(2) . . ?
C14' C13' H13C 109.4 . . ?
C12' C13' H13C 109.4 . . ?
C14' C13' H13D 109.4 . . ?
C12' C13' H13D 109.4 . . ?
H13C C13' H13D 108.0 . . ?
C13' C14' C15' 99.6(15) . . ?
C13' C14' H14C 111.9 . . ?
C15' C14' H14C 111.8 . . ?
C13' C14' H14D 111.8 . . ?
C15' C14' H14D 111.8 . . ?
H14C C14' H14D 109.6 . . ?
N14' C15' C14' 107.9(14) . . ?
N14' C15' H15G 110.1 . . ?
C14' C15' H15G 110.1 . . ?
N14' C15' H15H 110.1 . . ?
C14' C15' H15H 110.1 . . ?
H15G C15' H15H 108.4 . . ?
N14' C16' H16D 109.5 . . ?
N14' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
N14' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
H15C O15 H15D 103(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
C1 N1 N2 O1 27.9(2) . . . . ?
C2 N1 N2 O1 153.54(18) . . . . ?
C1 N1 N2 O2 -157.00(17) . . . . ?
C2 N1 N2 O2 -31.3(2) . . . . ?
C1 N3 N4 O4 -165.06(19) . . . . ?
C3 N3 N4 O4 -19.4(3) . . . . ?
C1 N3 N4 O3 15.8(3) . . . . ?
C3 N3 N4 O3 161.47(18) . . . . ?
C4 N5 N6 O6 170.18(18) . . . . ?
C5 N5 N6 O6 37.4(2) . . . . ?
C4 N5 N6 O5 -14.0(2) . . . . ?
C5 N5 N6 O5 -146.86(18) . . . . ?
C4 N7 N8 O7 15.2(3) . . . . ?
C6 N7 N8 O7 153.71(19) . . . . ?
C4 N7 N8 O8 -168.80(19) . . . . ?
C6 N7 N8 O8 -30.3(3) . . . . ?
C5 N9 N10 O10 33.5(2) . . . . ?
C2 N9 N10 O10 170.50(18) . . . . ?
C5 N9 N10 O9 -149.26(18) . . . . ?
C2 N9 N10 O9 -12.2(2) . . . . ?
C3 N11 N12 O12 -174.8(2) . . . . ?
C6 N11 N12 O12 -9.0(3) . . . . ?
C3 N11 N12 O11 7.4(3) . . . . ?
C6 N11 N12 O11 173.29(19) . . . . ?
N2 N1 C1 N3 91.85(17) . . . . ?
C2 N1 C1 N3 -37.68(17) . . . . ?
N2 N1 C1 C4 -149.97(15) . . . . ?
C2 N1 C1 C4 80.50(17) . . . . ?
N4 N3 C1 N1 -169.43(15) . . . . ?
C3 N3 C1 N1 41.52(18) . . . . ?
N4 N3 C1 C4 73.5(2) . . . . ?
C3 N3 C1 C4 -75.56(19) . . . . ?
N10 N9 C2 N1 -78.15(19) . . . . ?
C5 N9 C2 N1 57.8(2) . . . . ?
N10 N9 C2 C3 166.14(14) . . . . ?
C5 N9 C2 C3 -57.89(19) . . . . ?
N2 N1 C2 N9 135.56(16) . . . . ?
C1 N1 C2 N9 -94.87(17) . . . . ?
N2 N1 C2 C3 -107.15(17) . . . . ?
C1 N1 C2 C3 22.42(18) . . . . ?
N12 N11 C3 N3 111.20(19) . . . . ?
C6 N11 C3 N3 -55.2(2) . . . . ?
N12 N11 C3 C2 -138.02(18) . . . . ?
C6 N11 C3 C2 55.6(2) . . . . ?
N4 N3 C3 N11 -59.7(2) . . . . ?
C1 N3 C3 N11 88.88(19) . . . . ?
N4 N3 C3 C2 -176.09(16) . . . . ?
C1 N3 C3 C2 -27.50(18) . . . . ?
N9 C2 C3 N11 1.49(19) . . . . ?
N1 C2 C3 N11 -117.21(15) . . . . ?
N9 C2 C3 N3 121.49(15) . . . . ?
N1 C2 C3 N3 2.78(16) . . . . ?
N8 N7 C4 N5 110.64(18) . . . . ?
C6 N7 C4 N5 -31.63(18) . . . . ?
N8 N7 C4 C1 -134.06(17) . . . . ?
C6 N7 C4 C1 83.67(17) . . . . ?
N6 N5 C4 N7 -104.40(17) . . . . ?
C5 N5 C4 N7 32.71(18) . . . . ?
N6 N5 C4 C1 141.32(15) . . . . ?
C5 N5 C4 C1 -81.57(17) . . . . ?
N1 C1 C4 N7 -111.56(16) . . . . ?
N3 C1 C4 N7 -1.4(2) . . . . ?
N1 C1 C4 N5 0.52(19) . . . . ?
N3 C1 C4 N5 110.66(17) . . . . ?
N10 N9 C5 N5 78.97(19) . . . . ?
C2 N9 C5 N5 -57.3(2) . . . . ?
N10 N9 C5 C6 -167.10(14) . . . . ?
C2 N9 C5 C6 56.62(19) . . . . ?
N6 N5 C5 N9 -127.76(17) . . . . ?
C4 N5 C5 N9 95.06(18) . . . . ?
N6 N5 C5 C6 115.86(17) . . . . ?
C4 N5 C5 C6 -21.32(17) . . . . ?
N12 N11 C6 N7 -109.93(19) . . . . ?
C3 N11 C6 N7 56.6(2) . . . . ?
N12 N11 C6 C5 136.67(17) . . . . ?
C3 N11 C6 C5 -56.7(2) . . . . ?
N8 N7 C6 N11 118.91(18) . . . . ?
C4 N7 C6 N11 -98.52(17) . . . . ?
N8 N7 C6 C5 -124.39(17) . . . . ?
C4 N7 C6 C5 18.18(18) . . . . ?
N9 C5 C6 N11 0.51(19) . . . . ?
N5 C5 C6 N11 118.86(15) . . . . ?
N9 C5 C6 N7 -116.42(15) . . . . ?
N5 C5 C6 N7 1.94(17) . . . . ?
C10 N13 C7 O13 -174.1(2) . . . . ?
C11 N13 C7 O13 -3.2(4) . . . . ?
C10 N13 C7 C8 4.8(3) . . . . ?
C11 N13 C7 C8 175.7(2) . . . . ?
O13 C7 C8 C9 -178.3(3) . . . . ?
N13 C7 C8 C9 2.8(3) . . . . ?
C7 C8 C9 C10 -8.5(4) . . . . ?
C7 N13 C10 C9 -9.9(3) . . . . ?
C11 N13 C10 C9 179.1(3) . . . . ?
C8 C9 C10 N13 10.8(4) . . . . ?
C15 N14 C12 O14 -177(3) . . . . ?
C16 N14 C12 O14 -8(2) . . . . ?
C15 N14 C12 C13 1.2(9) . . . . ?
C16 N14 C12 C13 170.3(7) . . . . ?
O14 C12 C13 C14 -176(2) . . . . ?
N14 C12 C13 C14 5.6(9) . . . . ?
C12 C13 C14 C15 -9.9(10) . . . . ?
C12 N14 C15 C14 -7.6(11) . . . . ?
C16 N14 C15 C14 -176.7(7) . . . . ?
C13 C14 C15 N14 10.4(11) . . . . ?
C16' N14' C12' O14' -1(4) . . . . ?
C15' N14' C12' O14' 179(3) . . . . ?
C16' N14' C12' C13' 171(2) . . . . ?
C15' N14' C12' C13' -9(2) . . . . ?
O14' C12' C13' C14' -170(2) . . . . ?
N14' C12' C13' C14' 18(3) . . . . ?
C12' C13' C14' C15' -17(3) . . . . ?
C12' N14' C15' C14' -2(2) . . . . ?
C16' N14' C15' C14' 178(2) . . . . ?
C13' C14' C15' N14' 12(2) . . . . ?

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
O15 H15D O13 0.844(18) 2.203(19) 3.043(3) 173(3) 3_656
O15 H15C O13 0.829(18) 1.953(19) 2.772(3) 170(3) 1_654

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.040
