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

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 N2 O10'
_chemical_formula_weight         530.43

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   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   26.032(7)
_cell_length_b                   8.8150(15)
_cell_length_c                   21.444(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.25(3)
_cell_angle_gamma                90.00
_cell_volume                     4617(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3936
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2192
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16709
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3936
_reflns_number_gt                2922
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0753P)²+1.1972P] 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         3936
_refine_ls_number_parameters     368
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.078
_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 0.18916(7) 1.25066(19) 0.28417(7) 0.0564(4) Uani 1 1 d . . .
O2 O 0.22806(7) 1.09986(19) 0.37073(7) 0.0613(4) Uani 1 1 d . . .
O3 O 0.03612(6) 0.80025(16) 0.12260(6) 0.0497(4) Uani 1 1 d . . .
O4 O 0.01723(11) 0.60950(18) 0.17519(8) 0.0826(7) Uani 1 1 d D . .
O5 O 0.00840(11) 0.33995(19) 0.16784(8) 0.0838(7) Uani 1 1 d . . .
H3 H 0.0141(16) 0.505(2) 0.173(2) 0.120(13) Uiso 1 1 d D . .
O6 O 0.01485(7) 0.16271(16) 0.10118(7) 0.0544(4) Uani 1 1 d . . .
O7 O 0.28283(8) -0.03170(19) 0.12940(8) 0.0655(5) Uani 1 1 d . . .
O8 O 0.35270(8) -0.0443(2) 0.09423(9) 0.0760(5) Uani 1 1 d . . .
O9 O 0.37124(9) 0.0165(3) -0.00601(13) 0.0905(7) Uani 1 1 d D . .
H4 H 0.3698(14) -0.007(4) 0.0348(11) 0.098(11) Uiso 1 1 d D . .
O10 O 0.34070(8) 0.1673(2) -0.09063(10) 0.0788(6) Uani 1 1 d . . .
N1 N 0.06310(7) 1.0890(2) -0.25364(9) 0.0469(4) Uani 1 1 d . . .
H2 H 0.0527(12) 1.120(3) -0.2950(16) 0.082(9) Uiso 1 1 d . . .
N2 N 0.14493(6) 0.91287(17) 0.08162(7) 0.0360(4) Uani 1 1 d . . .
C1 C 0.06921(8) 0.9433(3) -0.23796(10) 0.0470(5) Uani 1 1 d . . .
H1A H 0.0619 0.8708 -0.2714 0.056 Uiso 1 1 calc R . .
C2 C 0.08643(8) 0.8980(2) -0.17206(9) 0.0435(5) Uani 1 1 d . . .
H2A H 0.0916 0.7958 -0.1608 0.052 Uiso 1 1 calc R . .
C3 C 0.07260(9) 1.1965(3) -0.20793(10) 0.0496(5) Uani 1 1 d . . .
H3A H 0.0682 1.2979 -0.2206 0.060 Uiso 1 1 calc R . .
C4 C 0.08884(9) 1.1588(2) -0.14203(10) 0.0469(5) Uani 1 1 d . . .
H4A H 0.0952 1.2343 -0.1100 0.056 Uiso 1 1 calc R . .
C5 C 0.09576(8) 1.0080(2) -0.12328(9) 0.0388(4) Uani 1 1 d . . .
C6 C 0.11246(8) 0.9685(2) -0.05184(9) 0.0376(4) Uani 1 1 d . . .
C7 C 0.08602(8) 1.0363(2) -0.01290(9) 0.0442(5) Uani 1 1 d . . .
H7A H 0.0569 1.1020 -0.0322 0.053 Uiso 1 1 calc R . .
C8 C 0.10267(8) 1.0070(2) 0.05342(9) 0.0421(5) Uani 1 1 d . . .
H8A H 0.0847 1.0523 0.0793 0.050 Uiso 1 1 calc R . .
C9 C 0.15462(8) 0.8687(2) -0.02215(9) 0.0424(5) Uani 1 1 d . . .
H9A H 0.1721 0.8195 -0.0476 0.051 Uiso 1 1 calc R . .
C10 C 0.17076(8) 0.8420(2) 0.04502(9) 0.0423(5) Uani 1 1 d . . .
H10A H 0.1994 0.7754 0.0652 0.051 Uiso 1 1 calc R . .
C11 C 0.16415(8) 0.8895(2) 0.15309(9) 0.0384(4) Uani 1 1 d . . .
C12 C 0.17026(8) 0.7425(2) 0.17707(10) 0.0444(5) Uani 1 1 d . . .
H12A H 0.1618 0.6602 0.1481 0.053 Uiso 1 1 calc R . .
C13 C 0.18921(9) 0.7207(3) 0.24502(10) 0.0509(5) Uani 1 1 d . . .
H13A H 0.1938 0.6229 0.2624 0.061 Uiso 1 1 calc R . .
C14 C 0.20133(9) 0.8439(3) 0.28711(10) 0.0494(5) Uani 1 1 d . . .
H14A H 0.2147 0.8280 0.3328 0.059 Uiso 1 1 calc R . .
C15 C 0.17510(8) 1.0143(2) 0.19439(9) 0.0394(4) Uani 1 1 d . . .
H15A H 0.1699 1.1121 0.1770 0.047 Uiso 1 1 calc R . .
C16 C 0.19413(8) 0.9903(2) 0.26295(9) 0.0419(5) Uani 1 1 d . . .
C17 C 0.20594(8) 1.1186(3) 0.31142(10) 0.0461(5) Uani 1 1 d . . .
C18 C 0.01088(9) 0.2961(2) 0.11152(9) 0.0432(5) Uani 1 1 d . . .
C19 C 0.00569(8) 0.4118(2) 0.05725(9) 0.0364(4) Uani 1 1 d . . .
C20 C 0.01255(8) 0.5702(2) 0.06258(9) 0.0364(4) Uani 1 1 d . . .
C21 C 0.00718(8) 0.6516(2) 0.00546(9) 0.0381(4) Uani 1 1 d . . .
H21A H 0.0126 0.7559 0.0094 0.046 Uiso 1 1 calc R . .
C22 C 0.02405(9) 0.6652(2) 0.12454(9) 0.0433(5) Uani 1 1 d . . .
C23 C 0.30684(10) 0.0074(2) 0.09140(10) 0.0492(5) Uani 1 1 d . . .
C24 C 0.27953(9) 0.1296(2) 0.04049(9) 0.0424(5) Uani 1 1 d . . .
C25 C 0.29444(8) 0.1805(2) -0.01348(9) 0.0429(5) Uani 1 1 d . . .
C26 C 0.26412(8) 0.2990(2) -0.05116(9) 0.0425(5) Uani 1 1 d . . .
H26A H 0.2739 0.3334 -0.0865 0.051 Uiso 1 1 calc R . .
C27 C 0.33771(10) 0.1190(3) -0.03928(12) 0.0548(6) Uani 1 1 d . . .
H1 H 0.1991(14) 1.330(4) 0.3188(17) 0.100(10) 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 C17 1.308(3) . ?
O1 H1 0.99(4) . ?
O2 C17 1.212(2) . ?
O3 C22 1.235(2) . ?
O4 C22 1.259(3) . ?
O4 H3 0.928(19) . ?
O5 C18 1.291(2) . ?
O6 C18 1.208(2) . ?
O7 C23 1.235(3) . ?
O8 C23 1.259(3) . ?
O9 C27 1.287(3) . ?
O9 H4 0.913(19) . ?
O10 C27 1.208(3) . ?
N1 C1 1.323(3) . ?
N1 C3 1.324(3) . ?
N1 H2 0.88(3) . ?
N2 C8 1.343(3) . ?
N2 C10 1.350(3) . ?
N2 C11 1.453(2) . ?
C1 C2 1.385(3) . ?
C1 H1A 0.9300 . ?
C2 C5 1.385(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.482(3) . ?
C6 C9 1.378(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.360(3) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C10 1.374(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C15 1.379(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.380(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13A 0.9300 . ?
C14 C16 1.379(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.396(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.494(3) . ?
C18 C19 1.518(3) . ?
C19 C21 1.386(3) 5_565 ?
C19 C20 1.407(3) . ?
C20 C21 1.384(3) . ?
C20 C22 1.511(3) . ?
C21 C19 1.386(3) 5_565 ?
C21 H21A 0.9300 . ?
C23 C24 1.523(3) . ?
C24 C26 1.385(3) 7 ?
C24 C25 1.415(3) . ?
C25 C26 1.388(3) . ?
C25 C27 1.516(3) . ?
C26 C24 1.385(3) 7 ?
C26 H26A 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
C17 O1 H1 110(2) . . ?
C22 O4 H3 113(2) . . ?
C27 O9 H4 117(2) . . ?
C1 N1 C3 122.12(18) . . ?
C1 N1 H2 122(2) . . ?
C3 N1 H2 116(2) . . ?
C8 N2 C10 121.27(16) . . ?
C8 N2 C11 119.47(15) . . ?
C10 N2 C11 119.25(16) . . ?
N1 C1 C2 120.47(19) . . ?
N1 C1 H1A 119.8 . . ?
C2 C1 H1A 119.8 . . ?
C5 C2 C1 118.61(19) . . ?
C5 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
N1 C3 C4 120.1(2) . . ?
N1 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C2 118.85(17) . . ?
C4 C5 C6 119.27(17) . . ?
C2 C5 C6 121.88(17) . . ?
C9 C6 C7 118.58(17) . . ?
C9 C6 C5 121.95(17) . . ?
C7 C6 C5 119.44(17) . . ?
C8 C7 C6 120.15(18) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
N2 C8 C7 120.20(18) . . ?
N2 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C10 C9 C6 119.94(18) . . ?
C10 C9 H9A 120.0 . . ?
C6 C9 H9A 120.0 . . ?
N2 C10 C9 119.81(18) . . ?
N2 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C15 C11 C12 122.50(17) . . ?
C15 C11 N2 118.92(17) . . ?
C12 C11 N2 118.58(17) . . ?
C13 C12 C11 118.40(19) . . ?
C13 C12 H12A 120.8 . . ?
C11 C12 H12A 120.8 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C16 121.41(18) . . ?
C13 C14 H14A 119.3 . . ?
C16 C14 H14A 119.3 . . ?
C11 C15 C16 118.33(18) . . ?
C11 C15 H15A 120.8 . . ?
C16 C15 H15A 120.8 . . ?
C14 C16 C15 119.36(19) . . ?
C14 C16 C17 118.59(18) . . ?
C15 C16 C17 122.03(19) . . ?
O2 C17 O1 123.7(2) . . ?
O2 C17 C16 122.4(2) . . ?
O1 C17 C16 113.97(17) . . ?
O6 C18 O5 119.89(18) . . ?
O6 C18 C19 120.25(17) . . ?
O5 C18 C19 119.77(17) . . ?
C21 C19 C20 117.38(16) 5_565 . ?
C21 C19 C18 113.64(16) 5_565 . ?
C20 C19 C18 128.97(16) . . ?
C21 C20 C19 118.12(16) . . ?
C21 C20 C22 114.78(16) . . ?
C19 C20 C22 127.09(16) . . ?
C20 C21 C19 124.49(18) . 5_565 ?
C20 C21 H21A 117.8 . . ?
C19 C21 H21A 117.8 5_565 . ?
O3 C22 O4 121.22(17) . . ?
O3 C22 C20 118.71(17) . . ?
O4 C22 C20 119.85(18) . . ?
O7 C23 O8 123.7(2) . . ?
O7 C23 C24 116.9(2) . . ?
O8 C23 C24 119.3(2) . . ?
C26 C24 C25 117.65(18) 7 . ?
C26 C24 C23 114.13(18) 7 . ?
C25 C24 C23 128.2(2) . . ?
C26 C25 C24 116.94(19) . . ?
C26 C25 C27 113.65(18) . . ?
C24 C25 C27 129.33(19) . . ?
C24 C26 C25 125.41(19) 7 . ?
C24 C26 H26A 117.3 7 . ?
C25 C26 H26A 117.3 . . ?
O10 C27 O9 120.5(2) . . ?
O10 C27 C25 119.8(2) . . ?
O9 C27 C25 119.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 -0.5(3) . . . . ?
N1 C1 C2 C5 1.6(3) . . . . ?
C1 N1 C3 C4 -0.6(3) . . . . ?
N1 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C2 0.5(3) . . . . ?
C3 C4 C5 C6 -178.98(19) . . . . ?
C1 C2 C5 C4 -1.6(3) . . . . ?
C1 C2 C5 C6 177.93(18) . . . . ?
C4 C5 C6 C9 -131.7(2) . . . . ?
C2 C5 C6 C9 48.8(3) . . . . ?
C4 C5 C6 C7 46.7(3) . . . . ?
C2 C5 C6 C7 -132.8(2) . . . . ?
C9 C6 C7 C8 1.6(3) . . . . ?
C5 C6 C7 C8 -176.73(19) . . . . ?
C10 N2 C8 C7 -1.9(3) . . . . ?
C11 N2 C8 C7 176.54(18) . . . . ?
C6 C7 C8 N2 0.3(3) . . . . ?
C7 C6 C9 C10 -2.0(3) . . . . ?
C5 C6 C9 C10 176.28(19) . . . . ?
C8 N2 C10 C9 1.5(3) . . . . ?
C11 N2 C10 C9 -176.96(18) . . . . ?
C6 C9 C10 N2 0.5(3) . . . . ?
C8 N2 C11 C15 -50.3(2) . . . . ?
C10 N2 C11 C15 128.2(2) . . . . ?
C8 N2 C11 C12 129.1(2) . . . . ?
C10 N2 C11 C12 -52.4(2) . . . . ?
C15 C11 C12 C13 -1.5(3) . . . . ?
N2 C11 C12 C13 179.18(18) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C16 1.1(3) . . . . ?
C12 C11 C15 C16 1.4(3) . . . . ?
N2 C11 C15 C16 -179.29(17) . . . . ?
C13 C14 C16 C15 -1.2(3) . . . . ?
C13 C14 C16 C17 177.5(2) . . . . ?
C11 C15 C16 C14 0.0(3) . . . . ?
C11 C15 C16 C17 -178.71(18) . . . . ?
C14 C16 C17 O2 9.6(3) . . . . ?
C15 C16 C17 O2 -171.7(2) . . . . ?
C14 C16 C17 O1 -168.88(18) . . . . ?
C15 C16 C17 O1 9.8(3) . . . . ?
O6 C18 C19 C21 14.8(3) . . . 5_565 ?
O5 C18 C19 C21 -161.9(2) . . . 5_565 ?
O6 C18 C19 C20 -164.7(2) . . . . ?
O5 C18 C19 C20 18.6(3) . . . . ?
C21 C19 C20 C21 -1.4(3) 5_565 . . . ?
C18 C19 C20 C21 178.08(19) . . . . ?
C21 C19 C20 C22 177.02(18) 5_565 . . . ?
C18 C19 C20 C22 -3.5(3) . . . . ?
C19 C20 C21 C19 1.5(3) . . . 5_565 ?
C22 C20 C21 C19 -177.12(18) . . . 5_565 ?
C21 C20 C22 O3 -11.1(3) . . . . ?
C19 C20 C22 O3 170.52(19) . . . . ?
C21 C20 C22 O4 163.6(2) . . . . ?
C19 C20 C22 O4 -14.8(3) . . . . ?
O7 C23 C24 C26 11.1(3) . . . 7 ?
O8 C23 C24 C26 -166.61(19) . . . 7 ?
O7 C23 C24 C25 -171.25(19) . . . . ?
O8 C23 C24 C25 11.1(3) . . . . ?
C26 C24 C25 C26 0.4(3) 7 . . . ?
C23 C24 C25 C26 -177.19(18) . . . . ?
C26 C24 C25 C27 -176.14(19) 7 . . . ?
C23 C24 C25 C27 6.2(3) . . . . ?
C24 C25 C26 C24 -0.5(3) . . . 7 ?
C27 C25 C26 C24 176.64(18) . . . 7 ?
C26 C25 C27 O10 -4.6(3) . . . . ?
C24 C25 C27 O10 172.0(2) . . . . ?
C26 C25 C27 O9 174.9(2) . . . . ?
C24 C25 C27 O9 -8.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 958696'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H40 N4 O17'
_chemical_formula_weight         896.80

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3700(15)
_cell_length_b                   9.5200(19)
_cell_length_c                   15.776(3)
_cell_angle_alpha                90.26(3)
_cell_angle_beta                 102.68(3)
_cell_angle_gamma                106.00(3)
_cell_volume                     1035.6(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3531
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7450
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3531
_reflns_number_gt                2241
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0666P)²+0.0000P] 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         3531
_refine_ls_number_parameters     305
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.041
_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 0.6508(3) 0.2665(2) -0.00523(10) 0.0589(5) Uani 1 1 d D . .
H1 H 0.5780 0.2424 -0.0559 0.088 Uiso 1 1 d RD . .
O2 O 0.5984(3) 0.06797(18) 0.06909(11) 0.0568(5) Uani 1 1 d . . .
O3 O 0.2345(3) 0.61236(18) 0.50380(13) 0.0518(5) Uani 1 1 d D . .
H2 H 0.221(5) 0.5291(15) 0.4890(17) 0.078 Uiso 1 1 d D . .
O4 O 0.5449(3) 0.63357(17) 0.51140(13) 0.0516(5) Uani 1 1 d . . .
O5 O 0.5923(3) 1.29309(18) 0.66767(11) 0.0523(5) Uani 1 1 d . . .
O6 O 0.3849(3) 1.09791(18) 0.70114(11) 0.0503(5) Uani 1 1 d . . .
O8 O -0.0449(7) 0.9457(5) 0.5629(3) 0.0791(13) Uani 0.50 1 d P . .
H6 H 0.0021 1.0307 0.5472 0.119 Uiso 0.50 1 d PR . .
H5 H -0.0188 0.8951 0.5251 0.119 Uiso 0.50 1 d PR . .
O9 O 0.4045(3) 1.2630(2) 0.83649(11) 0.0492(4) Uani 1 1 d D . .
H7 H 0.4093 1.2090 0.7945 0.074 Uiso 1 1 d RD . .
H8 H 0.461(5) 1.354(2) 0.834(2) 0.091(12) Uiso 1 1 d D . .
N1 N 1.3816(4) 1.4440(2) 0.17397(18) 0.0606(6) Uani 1 1 d . . .
N2 N 1.0206(3) 0.68819(19) 0.21277(11) 0.0338(4) Uani 1 1 d . . .
C1 C 1.3133(4) 1.3485(3) 0.1043(2) 0.0591(7) Uani 1 1 d . . .
H1A H 1.3162 1.3845 0.0498 0.071 Uiso 1 1 calc R . .
C2 C 1.2387(4) 1.1997(3) 0.10841(18) 0.0531(7) Uani 1 1 d . . .
H2A H 1.1942 1.1377 0.0579 0.064 Uiso 1 1 calc R . .
C3 C 1.3725(4) 1.3899(3) 0.2506(2) 0.0544(7) Uani 1 1 d . . .
H3A H 1.4188 1.4547 0.2999 0.065 Uiso 1 1 calc R . .
C4 C 1.2983(4) 1.2427(3) 0.26167(18) 0.0464(6) Uani 1 1 d . . .
H4A H 1.2935 1.2103 0.3169 0.056 Uiso 1 1 calc R . .
C5 C 1.2311(3) 1.1442(3) 0.18887(16) 0.0408(6) Uani 1 1 d . . .
C6 C 1.1574(3) 0.9851(2) 0.19846(15) 0.0377(5) Uani 1 1 d . . .
C7 C 1.1790(4) 0.8833(2) 0.14043(16) 0.0423(6) Uani 1 1 d . . .
H7A H 1.2398 0.9154 0.0954 0.051 Uiso 1 1 calc R . .
C8 C 1.1119(4) 0.7374(3) 0.14927(15) 0.0410(6) Uani 1 1 d . . .
H8A H 1.1294 0.6707 0.1108 0.049 Uiso 1 1 calc R . .
C9 C 1.0673(3) 0.9309(3) 0.26422(16) 0.0402(5) Uani 1 1 d . . .
H9A H 1.0530 0.9956 0.3049 0.048 Uiso 1 1 calc R . .
C10 C 0.9985(3) 0.7831(2) 0.27035(15) 0.0389(5) Uani 1 1 d . . .
H10A H 0.9363 0.7483 0.3145 0.047 Uiso 1 1 calc R . .
C11 C 0.9441(3) 0.5314(2) 0.21829(14) 0.0333(5) Uani 1 1 d . . .
C12 C 0.9695(3) 0.4717(3) 0.29802(14) 0.0401(6) Uani 1 1 d . . .
H12A H 1.0361 0.5308 0.3486 0.048 Uiso 1 1 calc R . .
C13 C 0.8940(4) 0.3224(3) 0.30123(15) 0.0433(6) Uani 1 1 d . . .
H13A H 0.9089 0.2804 0.3545 0.052 Uiso 1 1 calc R . .
C14 C 0.7966(4) 0.2349(3) 0.22580(15) 0.0406(6) Uani 1 1 d . . .
H14A H 0.7464 0.1345 0.2286 0.049 Uiso 1 1 calc R . .
C15 C 0.7734(3) 0.2958(2) 0.14646(14) 0.0346(5) Uani 1 1 d . . .
C16 C 0.8461(3) 0.4455(2) 0.14250(14) 0.0347(5) Uani 1 1 d . . .
H16A H 0.8290 0.4878 0.0894 0.042 Uiso 1 1 calc R . .
C17 C 0.6668(4) 0.2056(3) 0.06287(15) 0.0409(6) Uani 1 1 d . . .
C19 C 0.4937(3) 1.1694(2) 0.65026(14) 0.0322(5) Uani 1 1 d . . .
C18 C 0.3989(3) 0.6839(2) 0.50345(14) 0.0343(5) Uani 1 1 d . . .
C20 C 0.4466(3) 0.8477(2) 0.49891(13) 0.0300(5) Uani 1 1 d . . .
C22 C 0.4893(3) 1.0821(2) 0.57094(13) 0.0280(5) Uani 1 1 d . . .
C21 C 0.4358(3) 0.9300(2) 0.56856(14) 0.0301(5) Uani 1 1 d . . .
H21A H 0.3920 0.8831 0.6149 0.036 Uiso 1 1 calc R . .
O7 O 0.0848(4) 0.2755(3) 0.54143(16) 0.0932(8) Uani 1 1 d D . .
H3 H 0.2000 0.3153 0.5365 0.140 Uiso 1 1 d RD . .
H4 H -0.0076 0.3126 0.5222 0.140 Uiso 1 1 d R . .


_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 C17 1.221(3) . ?
O2 C17 1.281(3) . ?
O3 C18 1.217(3) . ?
O4 C18 1.276(3) . ?
O5 C19 1.195(3) . ?
O6 C19 1.318(3) . ?
N1 C3 1.324(4) . ?
N1 C1 1.335(4) . ?
N2 C8 1.342(3) . ?
N2 C10 1.344(3) . ?
N2 C11 1.453(3) . ?
C1 C2 1.378(4) . ?
C2 C5 1.384(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.388(3) . ?
C5 C6 1.483(3) . ?
C6 C9 1.379(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.358(3) . ?
C9 C10 1.369(3) . ?
C11 C12 1.379(3) . ?
C11 C16 1.381(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.378(3) . ?
C15 C16 1.385(3) . ?
C15 C17 1.502(3) . ?
C19 C22 1.489(3) . ?
C18 C20 1.507(3) . ?
C20 C21 1.376(3) . ?
C20 C22 1.395(3) 2_676 ?
C22 C21 1.389(3) . ?
C22 C20 1.395(3) 2_676 ?

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
C3 N1 C1 116.7(2) . . ?
C8 N2 C10 120.3(2) . . ?
C8 N2 C11 119.50(18) . . ?
C10 N2 C11 120.21(18) . . ?
N1 C1 C2 123.9(3) . . ?
C1 C2 C5 118.9(3) . . ?
N1 C3 C4 123.9(3) . . ?
C3 C4 C5 118.8(3) . . ?
C2 C5 C4 117.8(2) . . ?
C2 C5 C6 121.9(2) . . ?
C4 C5 C6 120.4(2) . . ?
C9 C6 C7 117.2(2) . . ?
C9 C6 C5 122.5(2) . . ?
C7 C6 C5 120.3(2) . . ?
C8 C7 C6 120.4(2) . . ?
N2 C8 C7 121.0(2) . . ?
C10 C9 C6 120.9(2) . . ?
N2 C10 C9 120.3(2) . . ?
C12 C11 C16 121.5(2) . . ?
C12 C11 N2 120.0(2) . . ?
C16 C11 N2 118.5(2) . . ?
C11 C12 C13 118.6(2) . . ?
C12 C13 C14 120.5(2) . . ?
C15 C14 C13 120.3(2) . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 C17 122.3(2) . . ?
C16 C15 C17 117.9(2) . . ?
C11 C16 C15 119.3(2) . . ?
O1 C17 O2 124.7(2) . . ?
O1 C17 C15 119.0(2) . . ?
O2 C17 C15 116.3(2) . . ?
O5 C19 O6 122.7(2) . . ?
O5 C19 C22 122.7(2) . . ?
O6 C19 C22 114.63(18) . . ?
O3 C18 O4 125.6(2) . . ?
O3 C18 C20 120.2(2) . . ?
O4 C18 C20 114.2(2) . . ?
C21 C20 C22 119.48(18) . 2_676 ?
C21 C20 C18 118.21(18) . . ?
C22 C20 C18 122.21(18) 2_676 . ?
C21 C22 C20 119.35(19) . 2_676 ?
C21 C22 C19 120.29(19) . . ?
C20 C22 C19 120.17(18) 2_676 . ?
C20 C21 C22 121.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 958697'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 N2 O6'
_chemical_formula_weight         403.36

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   P21/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                   8.9819(18)
_cell_length_b                   12.923(3)
_cell_length_c                   15.042(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.40(3)
_cell_angle_gamma                90.00
_cell_volume                     1731.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3060
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      25.03

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13377
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3060
_reflns_number_gt                1816
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0632P)²+0.0000P] 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         3060
_refine_ls_number_parameters     277
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.057
_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 0.2063(3) -0.30780(14) 0.21856(13) 0.0609(6) Uani 1 1 d D . .
H1 H 0.246(4) -0.3732(16) 0.219(2) 0.073 Uiso 1 1 d D . .
O2 O 0.3699(3) -0.27575(14) 0.33945(12) 0.0582(6) Uani 1 1 d . . .
O3 O 0.1206(2) 0.23881(12) -0.03261(11) 0.0486(5) Uani 1 1 d D . .
H2 H 0.144(3) 0.1749(15) -0.0182(17) 0.058 Uiso 1 1 d D . .
O4 O 0.0782(3) 0.24789(14) 0.10863(12) 0.0698(7) Uani 1 1 d . . .
O5 O 0.3156(2) 0.52224(13) 0.18598(12) 0.0527(5) Uani 1 1 d . . .
O6 O 0.3474(3) 0.38493(16) 0.10482(12) 0.0663(7) Uani 1 1 d . . .
N1 N 0.3274(3) 0.12655(14) 0.33330(12) 0.0368(5) Uani 1 1 d . . .
N2 N 0.7697(3) 0.55363(15) 0.48425(15) 0.0494(6) Uani 1 1 d . . .
C1 C 0.2701(3) -0.24881(18) 0.28299(16) 0.0406(7) Uani 1 1 d . . .
C2 C 0.2062(3) -0.14236(17) 0.27669(15) 0.0369(6) Uani 1 1 d . . .
C3 C 0.0629(3) -0.12410(18) 0.23375(17) 0.0432(7) Uani 1 1 d . . .
H3A H 0.0053 -0.1791 0.2086 0.052 Uiso 1 1 calc R . .
C4 C 0.0053(3) -0.02602(19) 0.22789(17) 0.0468(7) Uani 1 1 d . . .
H4A H -0.0927 -0.0150 0.2012 0.056 Uiso 1 1 calc R . .
C5 C 0.0923(3) 0.05651(19) 0.26153(17) 0.0456(7) Uani 1 1 d . . .
H5A H 0.0545 0.1236 0.2566 0.055 Uiso 1 1 calc R . .
C6 C 0.2944(3) -0.06038(17) 0.31256(15) 0.0375(6) Uani 1 1 d . . .
H6A H 0.3902 -0.0715 0.3426 0.045 Uiso 1 1 calc R . .
C7 C 0.2349(3) 0.03826(17) 0.30219(15) 0.0372(6) Uani 1 1 d . . .
C8 C 0.3288(3) 0.21128(18) 0.28006(16) 0.0433(7) Uani 1 1 d . . .
H8A H 0.2713 0.2119 0.2240 0.052 Uiso 1 1 calc R . .
C9 C 0.4084(3) 0.12568(18) 0.41456(16) 0.0418(7) Uani 1 1 d . . .
H9A H 0.4056 0.0678 0.4510 0.050 Uiso 1 1 calc R . .
C10 C 0.4134(3) 0.29512(18) 0.30789(16) 0.0419(7) Uani 1 1 d . . .
H10A H 0.4128 0.3528 0.2709 0.050 Uiso 1 1 calc R . .
C11 C 0.4948(3) 0.20829(18) 0.44465(16) 0.0429(7) Uani 1 1 d . . .
H11A H 0.5502 0.2065 0.5013 0.052 Uiso 1 1 calc R . .
C12 C 0.5004(3) 0.29558(17) 0.39068(15) 0.0376(6) Uani 1 1 d . . .
C13 C 0.5953(3) 0.38512(17) 0.42139(15) 0.0376(6) Uani 1 1 d . . .
C14 C 0.5567(3) 0.48486(17) 0.39317(16) 0.0437(7) Uani 1 1 d . . .
H14A H 0.4719 0.4967 0.3520 0.052 Uiso 1 1 calc R . .
C15 C 0.7258(3) 0.37275(18) 0.47977(17) 0.0445(7) Uani 1 1 d . . .
H15A H 0.7567 0.3070 0.4994 0.053 Uiso 1 1 calc R . .
C16 C 0.6453(4) 0.56569(19) 0.42685(17) 0.0469(7) Uani 1 1 d . . .
H16A H 0.6170 0.6324 0.4087 0.056 Uiso 1 1 calc R . .
C17 C 0.8095(4) 0.45751(19) 0.50871(18) 0.0493(7) Uani 1 1 d . . .
H17A H 0.8981 0.4476 0.5471 0.059 Uiso 1 1 calc R . .
C18 C 0.0871(3) 0.28843(18) 0.03784(16) 0.0407(7) Uani 1 1 d . . .
C19 C 0.0473(3) 0.39950(16) 0.01832(14) 0.0341(6) Uani 1 1 d . . .
C20 C 0.1298(3) 0.48075(17) 0.06092(14) 0.0341(6) Uani 1 1 d . . .
C21 C -0.0798(3) 0.41925(17) -0.04137(15) 0.0371(6) Uani 1 1 d . . .
H21A H -0.1333 0.3639 -0.0692 0.044 Uiso 1 1 calc R . .
C22 C 0.2747(3) 0.46172(18) 0.12155(16) 0.0397(6) 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
O1 C1 1.306(3) . ?
O1 H1 0.917(17) . ?
O2 C1 1.204(3) . ?
O3 C18 1.307(3) . ?
O3 H2 0.874(17) . ?
O4 C18 1.199(3) . ?
O5 C22 1.263(3) . ?
O6 C22 1.232(3) . ?
N1 C9 1.340(3) . ?
N1 C8 1.358(3) . ?
N1 C7 1.453(3) . ?
N2 C16 1.330(4) . ?
N2 C17 1.331(3) . ?
C1 C2 1.489(3) . ?
C2 C3 1.384(4) . ?
C2 C6 1.389(3) . ?
C3 C4 1.368(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(4) . ?
C4 H4A 0.9300 . ?
C5 C7 1.367(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.383(3) . ?
C6 H6A 0.9300 . ?
C8 C10 1.358(4) . ?
C8 H8A 0.9300 . ?
C9 C11 1.362(3) . ?
C9 H9A 0.9300 . ?
C10 C12 1.382(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.394(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.476(3) . ?
C13 C15 1.380(4) . ?
C13 C14 1.387(3) . ?
C14 C16 1.370(4) . ?
C14 H14A 0.9300 . ?
C15 C17 1.368(4) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.499(3) . ?
C19 C21 1.382(4) . ?
C19 C20 1.393(3) . ?
C20 C21 1.387(3) 3_565 ?
C20 C22 1.510(4) . ?
C21 C20 1.387(3) 3_565 ?
C21 H21A 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
C1 O1 H1 114(2) . . ?
C18 O3 H2 109.7(17) . . ?
C9 N1 C8 120.0(2) . . ?
C9 N1 C7 120.55(19) . . ?
C8 N1 C7 119.4(2) . . ?
C16 N2 C17 117.5(2) . . ?
O2 C1 O1 124.8(2) . . ?
O2 C1 C2 123.9(2) . . ?
O1 C1 C2 111.3(2) . . ?
C3 C2 C6 120.0(2) . . ?
C3 C2 C1 121.0(2) . . ?
C6 C2 C1 118.9(3) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C7 C5 C4 119.0(2) . . ?
C7 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
C7 C6 C2 117.8(3) . . ?
C7 C6 H6A 121.1 . . ?
C2 C6 H6A 121.1 . . ?
C5 C7 C6 122.4(2) . . ?
C5 C7 N1 118.2(2) . . ?
C6 C7 N1 119.4(2) . . ?
N1 C8 C10 120.6(2) . . ?
N1 C8 H8A 119.7 . . ?
C10 C8 H8A 119.7 . . ?
N1 C9 C11 121.0(2) . . ?
N1 C9 H9A 119.5 . . ?
C11 C9 H9A 119.5 . . ?
C8 C10 C12 120.7(2) . . ?
C8 C10 H10A 119.7 . . ?
C12 C10 H10A 119.7 . . ?
C9 C11 C12 120.1(2) . . ?
C9 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C10 C12 C11 117.5(2) . . ?
C10 C12 C13 121.5(2) . . ?
C11 C12 C13 121.0(2) . . ?
C15 C13 C14 117.4(2) . . ?
C15 C13 C12 121.2(2) . . ?
C14 C13 C12 121.4(3) . . ?
C16 C14 C13 119.0(3) . . ?
C16 C14 H14A 120.5 . . ?
C13 C14 H14A 120.5 . . ?
C17 C15 C13 119.8(2) . . ?
C17 C15 H15A 120.1 . . ?
C13 C15 H15A 120.1 . . ?
N2 C16 C14 123.4(2) . . ?
N2 C16 H16A 118.3 . . ?
C14 C16 H16A 118.3 . . ?
N2 C17 C15 122.8(3) . . ?
N2 C17 H17A 118.6 . . ?
C15 C17 H17A 118.6 . . ?
O4 C18 O3 123.7(2) . . ?
O4 C18 C19 123.4(2) . . ?
O3 C18 C19 112.7(2) . . ?
C21 C19 C20 120.4(2) . . ?
C21 C19 C18 117.4(2) . . ?
C20 C19 C18 122.1(2) . . ?
C21 C20 C19 117.8(2) 3_565 . ?
C21 C20 C22 120.7(2) 3_565 . ?
C19 C20 C22 121.4(2) . . ?
C19 C21 C20 121.8(2) . 3_565 ?
C19 C21 H21A 119.1 . . ?
C20 C21 H21A 119.1 3_565 . ?
O6 C22 O5 123.1(3) . . ?
O6 C22 C20 116.5(2) . . ?
O5 C22 C20 120.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 -156.8(3) . . . . ?
O1 C1 C2 C3 24.5(3) . . . . ?
O2 C1 C2 C6 24.9(4) . . . . ?
O1 C1 C2 C6 -153.7(2) . . . . ?
C6 C2 C3 C4 -1.5(4) . . . . ?
C1 C2 C3 C4 -179.7(2) . . . . ?
C2 C3 C4 C5 2.8(4) . . . . ?
C3 C4 C5 C7 -1.4(4) . . . . ?
C3 C2 C6 C7 -1.2(3) . . . . ?
C1 C2 C6 C7 177.1(2) . . . . ?
C4 C5 C7 C6 -1.4(4) . . . . ?
C4 C5 C7 N1 177.0(2) . . . . ?
C2 C6 C7 C5 2.6(3) . . . . ?
C2 C6 C7 N1 -175.8(2) . . . . ?
C9 N1 C7 C5 135.0(3) . . . . ?
C8 N1 C7 C5 -43.5(3) . . . . ?
C9 N1 C7 C6 -46.5(3) . . . . ?
C8 N1 C7 C6 134.9(2) . . . . ?
C9 N1 C8 C10 0.9(4) . . . . ?
C7 N1 C8 C10 179.5(2) . . . . ?
C8 N1 C9 C11 -1.0(4) . . . . ?
C7 N1 C9 C11 -179.6(2) . . . . ?
N1 C8 C10 C12 0.4(4) . . . . ?
N1 C9 C11 C12 -0.1(4) . . . . ?
C8 C10 C12 C11 -1.5(4) . . . . ?
C8 C10 C12 C13 178.8(2) . . . . ?
C9 C11 C12 C10 1.4(4) . . . . ?
C9 C11 C12 C13 -178.9(2) . . . . ?
C10 C12 C13 C15 -150.9(3) . . . . ?
C11 C12 C13 C15 29.4(4) . . . . ?
C10 C12 C13 C14 29.4(4) . . . . ?
C11 C12 C13 C14 -150.3(2) . . . . ?
C15 C13 C14 C16 -2.6(4) . . . . ?
C12 C13 C14 C16 177.1(2) . . . . ?
C14 C13 C15 C17 1.3(4) . . . . ?
C12 C13 C15 C17 -178.4(2) . . . . ?
C17 N2 C16 C14 0.8(4) . . . . ?
C13 C14 C16 N2 1.6(4) . . . . ?
C16 N2 C17 C15 -2.2(4) . . . . ?
C13 C15 C17 N2 1.2(4) . . . . ?
O4 C18 C19 C21 -110.6(3) . . . . ?
O3 C18 C19 C21 64.2(3) . . . . ?
O4 C18 C19 C20 66.7(4) . . . . ?
O3 C18 C19 C20 -118.5(3) . . . . ?
C21 C19 C20 C21 0.1(4) . . . 3_565 ?
C18 C19 C20 C21 -177.0(2) . . . 3_565 ?
C21 C19 C20 C22 -175.8(2) . . . . ?
C18 C19 C20 C22 7.0(3) . . . . ?
C20 C19 C21 C20 -0.1(4) . . . 3_565 ?
C18 C19 C21 C20 177.2(2) . . . 3_565 ?
C21 C20 C22 O6 -147.0(2) 3_565 . . . ?
C19 C20 C22 O6 28.8(3) . . . . ?
C21 C20 C22 O5 33.6(3) 3_565 . . . ?
C19 C20 C22 O5 -150.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 1009254'
