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

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#
#                 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.
#
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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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# 
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#  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.
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data_ak399out

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ak_399
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H31 N3 O8'
_chemical_formula_sum            'C24 H31 N3 O8'
_chemical_formula_weight         489.52

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)   '

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

_cell_length_a                   12.154(2)
_cell_length_b                   7.8731(12)
_cell_length_c                   13.359(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.134(5)
_cell_angle_gamma                90.00
_cell_volume                     1262.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.097
_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      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  ?
_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            15118
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4301
_reflns_number_gt                2799
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0337P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0071(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_number_reflns         4301
_refine_ls_number_parameters     317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
C24 C 0.5277(3) 0.3134(6) -0.1512(3) 0.1284(17) Uani 1 1 d . . .
H24A H 0.5239 0.3225 -0.2234 0.193 Uiso 1 1 calc R . .
H24B H 0.4537 0.3028 -0.1352 0.193 Uiso 1 1 calc R . .
H24C H 0.5706 0.2150 -0.1272 0.193 Uiso 1 1 calc R . .
C1 C 0.7089(2) 0.1864(4) 0.4616(2) 0.0553(7) Uani 1 1 d . . .
H1 H 0.7152 0.1355 0.5292 0.066 Uiso 1 1 calc R . .
C2 C 0.6173(2) 0.4422(5) 0.4475(2) 0.0681(9) Uani 1 1 d . . .
C3 C 0.6018(3) 0.4905(5) 0.5540(2) 0.0897(11) Uani 1 1 d . . .
H3A H 0.6098 0.6111 0.5625 0.135 Uiso 1 1 calc R . .
H3B H 0.6569 0.4339 0.6020 0.135 Uiso 1 1 calc R . .
H3C H 0.5288 0.4569 0.5652 0.135 Uiso 1 1 calc R . .
C4 C 0.5402(3) 0.5345(6) 0.3671(3) 0.1125(14) Uani 1 1 d . . .
H4A H 0.5485 0.6547 0.3777 0.169 Uiso 1 1 calc R . .
H4B H 0.4647 0.5022 0.3703 0.169 Uiso 1 1 calc R . .
H4C H 0.5580 0.5057 0.3016 0.169 Uiso 1 1 calc R . .
C5 C 0.7933(2) 0.3291(3) 0.4595(2) 0.0504(7) Uani 1 1 d . . .
H5 H 0.8424 0.3419 0.5247 0.060 Uiso 1 1 calc R . .
C6 C 0.8574(2) 0.2793(3) 0.37469(19) 0.0469(7) Uani 1 1 d . . .
H6 H 0.8716 0.3779 0.3338 0.056 Uiso 1 1 calc R . .
C7 C 1.0485(2) 0.3029(4) 0.4523(2) 0.0610(8) Uani 1 1 d . . .
H7A H 1.1036 0.2387 0.4975 0.073 Uiso 1 1 calc R . .
H7B H 1.0209 0.3926 0.4915 0.073 Uiso 1 1 calc R . .
C8 C 1.1029(2) 0.3807(4) 0.3704(2) 0.0550(8) Uani 1 1 d . . .
C9 C 1.1744(3) 0.2851(6) 0.3242(3) 0.0945(12) Uani 1 1 d . . .
H9 H 1.1871 0.1720 0.3425 0.113 Uiso 1 1 calc R . .
C10 C 1.2275(4) 0.3559(11) 0.2508(4) 0.147(3) Uani 1 1 d . . .
H10 H 1.2768 0.2906 0.2204 0.176 Uiso 1 1 calc R . .
C11 C 1.2091(5) 0.5171(12) 0.2226(4) 0.146(3) Uani 1 1 d . . .
H11 H 1.2460 0.5638 0.1732 0.175 Uiso 1 1 calc R . .
C12 C 1.1360(4) 0.6140(6) 0.2661(3) 0.1088(16) Uani 1 1 d . . .
H12 H 1.1221 0.7259 0.2455 0.131 Uiso 1 1 calc R . .
C13 C 1.0831(3) 0.5456(5) 0.3404(2) 0.0728(9) Uani 1 1 d . . .
H13 H 1.0337 0.6115 0.3703 0.087 Uiso 1 1 calc R . .
C14 C 0.7766(2) 0.1543(3) 0.31360(19) 0.0457(7) Uani 1 1 d . . .
H14 H 0.7190 0.2179 0.2692 0.055 Uiso 1 1 calc R . .
C15 C 0.8233(2) 0.0213(3) 0.25349(19) 0.0454(7) Uani 1 1 d . . .
C16 C 0.8164(2) -0.1499(4) 0.2583(2) 0.0570(8) Uani 1 1 d . . .
H16 H 0.7812 -0.2100 0.3041 0.068 Uiso 1 1 calc R . .
C17 C 0.9166(2) 0.2060(3) 0.1329(2) 0.0522(8) Uani 1 1 d . . .
H17A H 0.9791 0.1805 0.0984 0.063 Uiso 1 1 calc R . .
H17B H 0.9423 0.2853 0.1871 0.063 Uiso 1 1 calc R . .
C18 C 0.8262(2) 0.2898(4) 0.0588(2) 0.0494(7) Uani 1 1 d . . .
H18 H 0.7895 0.2048 0.0112 0.059 Uiso 1 1 calc R . .
C19 C 0.8667(2) 0.4358(3) 0.00041(19) 0.0493(7) Uani 1 1 d . . .
H19 H 0.8911 0.3930 -0.0613 0.059 Uiso 1 1 calc R . .
C20 C 0.7608(2) 0.5392(4) -0.02723(19) 0.0522(7) Uani 1 1 d . . .
H20 H 0.7756 0.6607 -0.0336 0.063 Uiso 1 1 calc R . .
C21 C 0.6924(2) 0.5016(4) 0.0559(2) 0.0562(8) Uani 1 1 d . . .
H21 H 0.6878 0.6019 0.0985 0.067 Uiso 1 1 calc R . .
C22 C 0.5822(2) 0.4699(5) -0.1010(2) 0.0709(9) Uani 1 1 d . . .
C23 C 0.5234(3) 0.6321(5) -0.1367(3) 0.1071(14) Uani 1 1 d . . .
H23A H 0.5190 0.6418 -0.2088 0.161 Uiso 1 1 calc R . .
H23B H 0.5640 0.7270 -0.1043 0.161 Uiso 1 1 calc R . .
H23C H 0.4496 0.6311 -0.1197 0.161 Uiso 1 1 calc R . .
N1 N 0.88083(18) 0.0501(3) 0.17677(17) 0.0496(6) Uani 1 1 d . . .
N2 N 0.9091(2) -0.0978(3) 0.13603(19) 0.0648(7) Uani 1 1 d . . .
N3 N 0.8689(2) -0.2208(3) 0.1859(2) 0.0681(7) Uani 1 1 d . . .
O1 O 0.95720(14) 0.1919(2) 0.41273(13) 0.0541(5) Uani 1 1 d . . .
O2 O 0.72955(15) 0.4768(2) 0.43215(15) 0.0676(6) Uani 1 1 d . . .
O3 O 0.60453(15) 0.2663(3) 0.43334(16) 0.0710(6) Uani 1 1 d . . .
O4 O 0.72638(15) 0.0660(2) 0.38915(14) 0.0579(5) Uani 1 1 d . . .
O5 O 0.74575(15) 0.3656(2) 0.11367(13) 0.0622(6) Uani 1 1 d . . .
O6 O 0.58700(14) 0.4547(3) 0.00626(14) 0.0732(6) Uani 1 1 d . . .
O7 O 0.69587(15) 0.4708(3) -0.11572(13) 0.0649(6) Uani 1 1 d . . .
O8 O 0.95336(14) 0.5298(2) 0.05795(13) 0.0587(5) Uani 1 1 d . . .
H8 H 0.9331 0.5633 0.1102 0.088 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C24 C22 1.506(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C1 O4 1.395(3) . ?
C1 O3 1.412(3) . ?
C1 C5 1.525(4) . ?
C1 H1 0.9800 . ?
C2 O3 1.403(4) . ?
C2 O2 1.437(3) . ?
C2 C4 1.497(4) . ?
C2 C3 1.514(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 O2 1.413(3) . ?
C5 C6 1.524(3) . ?
C5 H5 0.9800 . ?
C6 O1 1.417(3) . ?
C6 C14 1.532(3) . ?
C6 H6 0.9800 . ?
C7 O1 1.444(3) . ?
C7 C8 1.496(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.369(4) . ?
C8 C9 1.369(4) . ?
C9 C10 1.375(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.332(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O4 1.438(3) . ?
C14 C15 1.486(3) . ?
C14 H14 0.9800 . ?
C15 N1 1.348(3) . ?
C15 C16 1.353(4) . ?
C16 N3 1.360(3) . ?
C16 H16 0.9300 . ?
C17 N1 1.456(3) . ?
C17 C18 1.509(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O5 1.441(3) . ?
C18 C19 1.515(4) . ?
C18 H18 0.9800 . ?
C19 O8 1.411(3) . ?
C19 C20 1.518(3) . ?
C19 H19 0.9800 . ?
C20 O7 1.419(3) . ?
C20 C21 1.519(3) . ?
C20 H20 0.9800 . ?
C21 O6 1.395(3) . ?
C21 O5 1.416(3) . ?
C21 H21 0.9800 . ?
C22 O7 1.425(3) . ?
C22 O6 1.430(3) . ?
C22 C23 1.504(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 N2 1.353(3) . ?
N2 N3 1.312(3) . ?
O8 H8 0.8200 . ?

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
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C1 O3 110.3(2) . . ?
O4 C1 C5 108.1(2) . . ?
O3 C1 C5 104.2(2) . . ?
O4 C1 H1 111.3 . . ?
O3 C1 H1 111.3 . . ?
C5 C1 H1 111.3 . . ?
O3 C2 O2 104.8(2) . . ?
O3 C2 C4 109.8(3) . . ?
O2 C2 C4 107.8(3) . . ?
O3 C2 C3 110.3(3) . . ?
O2 C2 C3 110.4(3) . . ?
C4 C2 C3 113.3(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 C6 110.1(2) . . ?
O2 C5 C1 105.5(2) . . ?
C6 C5 C1 104.4(2) . . ?
O2 C5 H5 112.1 . . ?
C6 C5 H5 112.1 . . ?
C1 C5 H5 112.1 . . ?
O1 C6 C5 111.6(2) . . ?
O1 C6 C14 108.6(2) . . ?
C5 C6 C14 101.6(2) . . ?
O1 C6 H6 111.5 . . ?
C5 C6 H6 111.5 . . ?
C14 C6 H6 111.5 . . ?
O1 C7 C8 112.5(2) . . ?
O1 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
O1 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C13 C8 C9 118.9(3) . . ?
C13 C8 C7 121.7(3) . . ?
C9 C8 C7 119.4(3) . . ?
C8 C9 C10 120.2(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.1(6) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.8(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 120.2(4) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O4 C14 C15 106.3(2) . . ?
O4 C14 C6 104.1(2) . . ?
C15 C14 C6 118.2(2) . . ?
O4 C14 H14 109.3 . . ?
C15 C14 H14 109.3 . . ?
C6 C14 H14 109.3 . . ?
N1 C15 C16 104.3(3) . . ?
N1 C15 C14 125.6(2) . . ?
C16 C15 C14 130.1(3) . . ?
C15 C16 N3 109.6(3) . . ?
C15 C16 H16 125.2 . . ?
N3 C16 H16 125.2 . . ?
N1 C17 C18 113.6(2) . . ?
N1 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N1 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
O5 C18 C17 109.2(2) . . ?
O5 C18 C19 104.4(2) . . ?
C17 C18 C19 114.1(2) . . ?
O5 C18 H18 109.6 . . ?
C17 C18 H18 109.6 . . ?
C19 C18 H18 109.6 . . ?
O8 C19 C18 113.1(2) . . ?
O8 C19 C20 112.5(2) . . ?
C18 C19 C20 101.6(2) . . ?
O8 C19 H19 109.8 . . ?
C18 C19 H19 109.8 . . ?
C20 C19 H19 109.8 . . ?
O7 C20 C21 103.8(2) . . ?
O7 C20 C19 109.7(2) . . ?
C21 C20 C19 105.0(2) . . ?
O7 C20 H20 112.6 . . ?
C21 C20 H20 112.6 . . ?
C19 C20 H20 112.6 . . ?
O6 C21 O5 111.5(2) . . ?
O6 C21 C20 105.8(2) . . ?
O5 C21 C20 106.8(2) . . ?
O6 C21 H21 110.9 . . ?
O5 C21 H21 110.9 . . ?
C20 C21 H21 110.9 . . ?
O7 C22 O6 104.6(2) . . ?
O7 C22 C23 112.0(3) . . ?
O6 C22 C23 109.2(3) . . ?
O7 C22 C24 108.1(3) . . ?
O6 C22 C24 108.9(3) . . ?
C23 C22 C24 113.6(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 N1 N2 110.9(2) . . ?
C15 N1 C17 132.2(2) . . ?
N2 N1 C17 116.9(2) . . ?
N3 N2 N1 107.0(2) . . ?
N2 N3 C16 108.2(2) . . ?
C6 O1 C7 113.67(19) . . ?
C5 O2 C2 107.5(2) . . ?
C2 O3 C1 109.2(2) . . ?
C1 O4 C14 106.7(2) . . ?
C21 O5 C18 108.98(19) . . ?
C21 O6 C22 110.0(2) . . ?
C20 O7 C22 108.1(2) . . ?
C19 O8 H8 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C1 C5 O2 118.3(2) . . . . ?
O3 C1 C5 O2 1.0(3) . . . . ?
O4 C1 C5 C6 2.3(3) . . . . ?
O3 C1 C5 C6 -115.1(2) . . . . ?
O2 C5 C6 O1 151.8(2) . . . . ?
C1 C5 C6 O1 -95.4(2) . . . . ?
O2 C5 C6 C14 -92.7(2) . . . . ?
C1 C5 C6 C14 20.2(3) . . . . ?
O1 C7 C8 C13 102.9(3) . . . . ?
O1 C7 C8 C9 -77.1(3) . . . . ?
C13 C8 C9 C10 1.8(5) . . . . ?
C7 C8 C9 C10 -178.2(4) . . . . ?
C8 C9 C10 C11 -0.9(8) . . . . ?
C9 C10 C11 C12 -0.6(10) . . . . ?
C10 C11 C12 C13 1.2(8) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
C7 C8 C13 C12 178.9(3) . . . . ?
C11 C12 C13 C8 -0.4(6) . . . . ?
O1 C6 C14 O4 81.9(2) . . . . ?
C5 C6 C14 O4 -35.8(2) . . . . ?
O1 C6 C14 C15 -35.7(3) . . . . ?
C5 C6 C14 C15 -153.4(2) . . . . ?
O4 C14 C15 N1 -177.8(2) . . . . ?
C6 C14 C15 N1 -61.4(3) . . . . ?
O4 C14 C15 C16 4.9(4) . . . . ?
C6 C14 C15 C16 121.3(3) . . . . ?
N1 C15 C16 N3 0.0(3) . . . . ?
C14 C15 C16 N3 177.8(2) . . . . ?
N1 C17 C18 O5 72.7(3) . . . . ?
N1 C17 C18 C19 -170.9(2) . . . . ?
O5 C18 C19 O8 84.6(2) . . . . ?
C17 C18 C19 O8 -34.6(3) . . . . ?
O5 C18 C19 C20 -36.2(2) . . . . ?
C17 C18 C19 C20 -155.4(2) . . . . ?
O8 C19 C20 O7 155.6(2) . . . . ?
C18 C19 C20 O7 -83.2(2) . . . . ?
O8 C19 C20 C21 -93.4(3) . . . . ?
C18 C19 C20 C21 27.9(3) . . . . ?
O7 C20 C21 O6 -13.6(3) . . . . ?
C19 C20 C21 O6 -128.8(2) . . . . ?
O7 C20 C21 O5 105.2(2) . . . . ?
C19 C20 C21 O5 -10.0(3) . . . . ?
C16 C15 N1 N2 -0.4(3) . . . . ?
C14 C15 N1 N2 -178.3(2) . . . . ?
C16 C15 N1 C17 -179.9(3) . . . . ?
C14 C15 N1 C17 2.2(4) . . . . ?
C18 C17 N1 C15 -80.9(3) . . . . ?
C18 C17 N1 N2 99.6(3) . . . . ?
C15 N1 N2 N3 0.6(3) . . . . ?
C17 N1 N2 N3 -179.8(2) . . . . ?
N1 N2 N3 C16 -0.5(3) . . . . ?
C15 C16 N3 N2 0.3(3) . . . . ?
C5 C6 O1 C7 -81.8(3) . . . . ?
C14 C6 O1 C7 167.0(2) . . . . ?
C8 C7 O1 C6 -79.0(3) . . . . ?
C6 C5 O2 C2 128.9(2) . . . . ?
C1 C5 O2 C2 16.7(3) . . . . ?
O3 C2 O2 C5 -28.5(3) . . . . ?
C4 C2 O2 C5 -145.5(3) . . . . ?
C3 C2 O2 C5 90.2(3) . . . . ?
O2 C2 O3 C1 29.7(3) . . . . ?
C4 C2 O3 C1 145.2(2) . . . . ?
C3 C2 O3 C1 -89.2(3) . . . . ?
O4 C1 O3 C2 -134.8(2) . . . . ?
C5 C1 O3 C2 -19.0(3) . . . . ?
O3 C1 O4 C14 87.5(2) . . . . ?
C5 C1 O4 C14 -25.9(3) . . . . ?
C15 C14 O4 C1 164.6(2) . . . . ?
C6 C14 O4 C1 39.1(2) . . . . ?
O6 C21 O5 C18 101.5(2) . . . . ?
C20 C21 O5 C18 -13.6(3) . . . . ?
C17 C18 O5 C21 154.2(2) . . . . ?
C19 C18 O5 C21 31.8(3) . . . . ?
O5 C21 O6 C22 -119.2(3) . . . . ?
C20 C21 O6 C22 -3.4(3) . . . . ?
O7 C22 O6 C21 19.2(3) . . . . ?
C23 C22 O6 C21 -100.9(3) . . . . ?
C24 C22 O6 C21 134.5(3) . . . . ?
C21 C20 O7 C22 25.9(3) . . . . ?
C19 C20 O7 C22 137.7(2) . . . . ?
O6 C22 O7 C20 -28.3(3) . . . . ?
C23 C22 O7 C20 89.9(3) . . . . ?
C24 C22 O7 C20 -144.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.027
_database_code_depnum_ccdc_archive 'CCDC 1026262'
#######################################################################
#
#                 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_ak685out

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ak_685
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H31 N3 O8'
_chemical_formula_sum            'C24 H31 N3 O8'
_chemical_formula_weight         489.52

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   'P1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.9472(7)
_cell_length_b                   8.8261(11)
_cell_length_c                   12.2179(15)
_cell_angle_alpha                87.740(4)
_cell_angle_beta                 87.485(4)
_cell_angle_gamma                77.734(4)
_cell_volume                     625.78(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.098
_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      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  ?
_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            7488
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0979
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3528
_reflns_number_gt                1903
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0521P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(17)
_refine_ls_number_reflns         3528
_refine_ls_number_parameters     316
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.005

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
C1 C 0.6215(9) 0.8445(7) 0.4481(5) 0.0596(17) Uani 1 1 d . . .
H1 H 0.7898 0.8210 0.4395 0.072 Uiso 1 1 calc R . .
C2 C 0.5295(9) 0.6950(6) 0.4641(5) 0.0505(14) Uani 1 1 d . . .
H2 H 0.6516 0.6012 0.4695 0.061 Uiso 1 1 calc R . .
C3 C 0.3802(8) 0.6986(6) 0.3654(4) 0.0468(14) Uani 1 1 d . . .
H3 H 0.4749 0.6461 0.3047 0.056 Uiso 1 1 calc R . .
C4 C 0.3099(8) 0.8703(6) 0.3367(4) 0.0461(14) Uani 1 1 d . . .
H4 H 0.1913 0.9183 0.3903 0.055 Uiso 1 1 calc R . .
C5 C 0.4595(11) 0.8351(7) 0.6206(5) 0.0627(16) Uani 1 1 d . . .
C6 C 0.2515(14) 0.9341(10) 0.6780(7) 0.121(3) Uani 1 1 d . . .
H6A H 0.1883 0.8718 0.7324 0.182 Uiso 1 1 calc R . .
H6B H 0.1374 0.9752 0.6254 0.182 Uiso 1 1 calc R . .
H6C H 0.2970 1.0180 0.7127 0.182 Uiso 1 1 calc R . .
C7 C 0.6469(12) 0.7643(8) 0.6976(5) 0.085(2) Uani 1 1 d . . .
H7A H 0.5877 0.7004 0.7523 0.128 Uiso 1 1 calc R . .
H7B H 0.6997 0.8452 0.7326 0.128 Uiso 1 1 calc R . .
H7C H 0.7729 0.7021 0.6571 0.128 Uiso 1 1 calc R . .
C8 C 0.2321(11) 0.4718(7) 0.3626(5) 0.0710(18) Uani 1 1 d . . .
H8A H 0.3889 0.4247 0.3812 0.085 Uiso 1 1 calc R . .
H8B H 0.2156 0.4573 0.2853 0.085 Uiso 1 1 calc R . .
C9 C 0.0669(9) 0.3954(6) 0.4297(5) 0.0498(14) Uani 1 1 d . . .
C10 C -0.0651(10) 0.3106(6) 0.3799(5) 0.0641(17) Uani 1 1 d . . .
H10 H -0.0555 0.3043 0.3039 0.077 Uiso 1 1 calc R . .
C11 C -0.2120(11) 0.2342(7) 0.4394(6) 0.0712(19) Uani 1 1 d . . .
H11 H -0.2978 0.1747 0.4048 0.085 Uiso 1 1 calc R . .
C12 C -0.2282(11) 0.2486(7) 0.5513(7) 0.077(2) Uani 1 1 d . . .
H12 H -0.3281 0.1995 0.5930 0.092 Uiso 1 1 calc R . .
C13 C -0.1010(11) 0.3326(7) 0.6014(5) 0.0744(19) Uani 1 1 d . . .
H13 H -0.1128 0.3400 0.6772 0.089 Uiso 1 1 calc R . .
C14 C 0.0470(10) 0.4083(6) 0.5412(5) 0.0606(16) Uani 1 1 d . . .
H14 H 0.1325 0.4675 0.5763 0.073 Uiso 1 1 calc R . .
C15 C 0.2273(9) 0.9171(6) 0.2249(4) 0.0437(13) Uani 1 1 d . . .
C16 C 0.0147(9) 0.9921(6) 0.1937(5) 0.0515(15) Uani 1 1 d . . .
H16 H -0.1102 1.0272 0.2413 0.062 Uiso 1 1 calc R . .
C17 C 0.5880(8) 0.8043(6) 0.1057(5) 0.0551(15) Uani 1 1 d . . .
H17A H 0.6636 0.7744 0.1744 0.066 Uiso 1 1 calc R . .
H17B H 0.6706 0.8735 0.0653 0.066 Uiso 1 1 calc R . .
C18 C 0.5961(8) 0.6630(6) 0.0409(4) 0.0497(14) Uani 1 1 d . . .
H18 H 0.5076 0.6902 -0.0255 0.060 Uiso 1 1 calc R . .
C19 C 0.8376(9) 0.5733(7) 0.0119(5) 0.0597(16) Uani 1 1 d . . .
H19 H 0.9014 0.6173 -0.0544 0.072 Uiso 1 1 calc R . .
C20 C 0.7969(9) 0.4129(7) -0.0073(5) 0.0564(16) Uani 1 1 d . . .
H20 H 0.9320 0.3300 0.0063 0.068 Uiso 1 1 calc R . .
C21 C 0.5878(9) 0.4019(7) 0.0698(4) 0.0538(16) Uani 1 1 d . . .
H21 H 0.6326 0.3263 0.1300 0.065 Uiso 1 1 calc R . .
C22 C 0.5226(10) 0.3303(7) -0.1051(5) 0.0551(15) Uani 1 1 d . . .
C23 C 0.3476(11) 0.4063(9) -0.1843(5) 0.082(2) Uani 1 1 d . . .
H23A H 0.2212 0.3542 -0.1808 0.123 Uiso 1 1 calc R . .
H23B H 0.4159 0.4009 -0.2570 0.123 Uiso 1 1 calc R . .
H23C H 0.2927 0.5130 -0.1661 0.123 Uiso 1 1 calc R . .
C24 C 0.6086(11) 0.1595(7) -0.1208(5) 0.080(2) Uani 1 1 d . . .
H24A H 0.4812 0.1083 -0.1149 0.120 Uiso 1 1 calc R . .
H24B H 0.7167 0.1178 -0.0656 0.120 Uiso 1 1 calc R . .
H24C H 0.6828 0.1434 -0.1920 0.120 Uiso 1 1 calc R . .
N1 N 0.0118(8) 1.0080(6) 0.0839(5) 0.0641(14) Uani 1 1 d . . .
N2 N 0.2208(9) 0.9437(6) 0.0429(4) 0.0617(13) Uani 1 1 d . . .
N3 N 0.3480(7) 0.8862(5) 0.1285(4) 0.0502(11) Uani 1 1 d . . .
O1 O 0.5197(5) 0.9249(4) 0.3537(3) 0.0529(10) Uani 1 1 d . . .
O2 O 0.5488(8) 0.9295(5) 0.5423(4) 0.0791(13) Uani 1 1 d . . .
O3 O 0.3868(6) 0.7220(4) 0.5609(3) 0.0623(11) Uani 1 1 d . . .
O4 O 0.1860(6) 0.6334(4) 0.3839(3) 0.0539(10) Uani 1 1 d . . .
O5 O 0.5004(6) 0.5507(4) 0.1100(3) 0.0562(10) Uani 1 1 d . . .
O6 O 0.9807(6) 0.5698(5) 0.1018(3) 0.0764(13) Uani 1 1 d . . .
H6 H 1.0013 0.6573 0.1110 0.115 Uiso 1 1 calc R . .
O7 O 0.7105(6) 0.4109(4) -0.1133(3) 0.0599(11) Uani 1 1 d . . .
O8 O 0.4302(6) 0.3563(5) 0.0049(3) 0.0684(12) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 1.401(6) . ?
C1 O1 1.420(6) . ?
C1 C2 1.535(7) . ?
C1 H1 0.9800 . ?
C2 O3 1.423(6) . ?
C2 C3 1.524(7) . ?
C2 H2 0.9800 . ?
C3 O4 1.401(5) . ?
C3 C4 1.516(7) . ?
C3 H3 0.9800 . ?
C4 O1 1.455(5) . ?
C4 C15 1.485(7) . ?
C4 H4 0.9800 . ?
C5 O2 1.404(7) . ?
C5 O3 1.408(6) . ?
C5 C7 1.506(8) . ?
C5 C6 1.516(8) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O4 1.426(6) . ?
C8 C9 1.503(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.370(7) . ?
C9 C10 1.369(7) . ?
C10 C11 1.379(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.346(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N3 1.358(6) . ?
C15 C16 1.360(7) . ?
C16 N1 1.344(6) . ?
C16 H16 0.9300 . ?
C17 N3 1.476(7) . ?
C17 C18 1.495(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O5 1.467(6) . ?
C18 C19 1.520(7) . ?
C18 H18 0.9800 . ?
C19 O6 1.414(6) . ?
C19 C20 1.514(8) . ?
C19 H19 0.9800 . ?
C20 O7 1.417(6) . ?
C20 C21 1.544(7) . ?
C20 H20 0.9800 . ?
C21 O8 1.386(6) . ?
C21 O5 1.405(6) . ?
C21 H21 0.9800 . ?
C22 O7 1.444(6) . ?
C22 O8 1.437(6) . ?
C22 C23 1.487(8) . ?
C22 C24 1.502(8) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 N2 1.336(6) . ?
N2 N3 1.337(6) . ?
O6 H6 0.8200 . ?

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
O2 C1 O1 110.8(5) . . ?
O2 C1 C2 105.7(4) . . ?
O1 C1 C2 107.5(4) . . ?
O2 C1 H1 110.9 . . ?
O1 C1 H1 110.9 . . ?
C2 C1 H1 110.9 . . ?
O3 C2 C1 103.1(4) . . ?
O3 C2 C3 109.6(4) . . ?
C1 C2 C3 103.3(5) . . ?
O3 C2 H2 113.3 . . ?
C1 C2 H2 113.3 . . ?
C3 C2 H2 113.3 . . ?
O4 C3 C4 110.8(4) . . ?
O4 C3 C2 115.4(4) . . ?
C4 C3 C2 102.9(4) . . ?
O4 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
O1 C4 C15 110.0(4) . . ?
O1 C4 C3 102.5(4) . . ?
C15 C4 C3 118.1(4) . . ?
O1 C4 H4 108.6 . . ?
C15 C4 H4 108.6 . . ?
C3 C4 H4 108.6 . . ?
O2 C5 O3 105.8(5) . . ?
O2 C5 C7 108.5(5) . . ?
O3 C5 C7 112.0(5) . . ?
O2 C5 C6 108.1(6) . . ?
O3 C5 C6 109.0(5) . . ?
C7 C5 C6 113.1(6) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 C9 109.6(5) . . ?
O4 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
O4 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C14 C9 C10 119.0(5) . . ?
C14 C9 C8 120.8(5) . . ?
C10 C9 C8 120.2(5) . . ?
C9 C10 C11 121.7(6) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 118.1(6) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C13 C12 C11 120.8(7) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.7(7) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 119.6(6) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
N3 C15 C16 103.7(5) . . ?
N3 C15 C4 127.0(5) . . ?
C16 C15 C4 129.2(5) . . ?
N1 C16 C15 109.9(5) . . ?
N1 C16 H16 125.0 . . ?
C15 C16 H16 125.0 . . ?
N3 C17 C18 111.0(4) . . ?
N3 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
N3 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
O5 C18 C17 108.4(4) . . ?
O5 C18 C19 102.7(4) . . ?
C17 C18 C19 114.5(4) . . ?
O5 C18 H18 110.3 . . ?
C17 C18 H18 110.3 . . ?
C19 C18 H18 110.3 . . ?
O6 C19 C20 110.6(5) . . ?
O6 C19 C18 109.8(4) . . ?
C20 C19 C18 102.1(4) . . ?
O6 C19 H19 111.3 . . ?
C20 C19 H19 111.3 . . ?
C18 C19 H19 111.3 . . ?
O7 C20 C19 109.0(5) . . ?
O7 C20 C21 103.5(4) . . ?
C19 C20 C21 103.6(4) . . ?
O7 C20 H20 113.3 . . ?
C19 C20 H20 113.3 . . ?
C21 C20 H20 113.3 . . ?
O8 C21 O5 111.0(4) . . ?
O8 C21 C20 105.7(4) . . ?
O5 C21 C20 107.2(4) . . ?
O8 C21 H21 110.9 . . ?
O5 C21 H21 110.9 . . ?
C20 C21 H21 110.9 . . ?
O7 C22 O8 104.3(4) . . ?
O7 C22 C23 107.9(5) . . ?
O8 C22 C23 109.5(5) . . ?
O7 C22 C24 110.9(5) . . ?
O8 C22 C24 109.8(5) . . ?
C23 C22 C24 114.1(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 N1 C16 108.3(5) . . ?
N3 N2 N1 106.5(4) . . ?
N2 N3 C15 111.5(4) . . ?
N2 N3 C17 117.7(5) . . ?
C15 N3 C17 130.8(4) . . ?
C1 O1 C4 107.2(4) . . ?
C5 O2 C1 109.1(4) . . ?
C5 O3 C2 108.2(4) . . ?
C3 O4 C8 112.7(4) . . ?
C21 O5 C18 108.3(4) . . ?
C19 O6 H6 109.5 . . ?
C20 O7 C22 108.1(4) . . ?
C21 O8 C22 110.7(4) . . ?

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 O3 7.5(6) . . . . ?
O1 C1 C2 O3 -110.9(5) . . . . ?
O2 C1 C2 C3 121.6(5) . . . . ?
O1 C1 C2 C3 3.3(6) . . . . ?
O3 C2 C3 O4 -37.4(6) . . . . ?
C1 C2 C3 O4 -146.7(4) . . . . ?
O3 C2 C3 C4 83.4(5) . . . . ?
C1 C2 C3 C4 -25.9(5) . . . . ?
O4 C3 C4 O1 163.3(4) . . . . ?
C2 C3 C4 O1 39.4(5) . . . . ?
O4 C3 C4 C15 -75.6(6) . . . . ?
C2 C3 C4 C15 160.5(4) . . . . ?
O4 C8 C9 C14 -55.2(8) . . . . ?
O4 C8 C9 C10 125.3(6) . . . . ?
C14 C9 C10 C11 -2.0(9) . . . . ?
C8 C9 C10 C11 177.6(6) . . . . ?
C9 C10 C11 C12 1.7(10) . . . . ?
C10 C11 C12 C13 -1.1(10) . . . . ?
C11 C12 C13 C14 0.8(10) . . . . ?
C10 C9 C14 C13 1.6(9) . . . . ?
C8 C9 C14 C13 -177.9(6) . . . . ?
C12 C13 C14 C9 -1.0(9) . . . . ?
O1 C4 C15 N3 55.3(6) . . . . ?
C3 C4 C15 N3 -61.9(7) . . . . ?
O1 C4 C15 C16 -128.5(5) . . . . ?
C3 C4 C15 C16 114.4(6) . . . . ?
N3 C15 C16 N1 -1.4(6) . . . . ?
C4 C15 C16 N1 -178.3(5) . . . . ?
N3 C17 C18 O5 -67.3(5) . . . . ?
N3 C17 C18 C19 178.8(5) . . . . ?
O5 C18 C19 O6 -77.5(5) . . . . ?
C17 C18 C19 O6 39.7(7) . . . . ?
O5 C18 C19 C20 39.9(5) . . . . ?
C17 C18 C19 C20 157.1(5) . . . . ?
O6 C19 C20 O7 -163.8(4) . . . . ?
C18 C19 C20 O7 79.5(5) . . . . ?
O6 C19 C20 C21 86.6(5) . . . . ?
C18 C19 C20 C21 -30.2(5) . . . . ?
O7 C20 C21 O8 14.6(6) . . . . ?
C19 C20 C21 O8 128.3(5) . . . . ?
O7 C20 C21 O5 -104.0(5) . . . . ?
C19 C20 C21 O5 9.8(6) . . . . ?
C15 C16 N1 N2 0.1(6) . . . . ?
C16 N1 N2 N3 1.3(5) . . . . ?
N1 N2 N3 C15 -2.3(5) . . . . ?
N1 N2 N3 C17 178.5(4) . . . . ?
C16 C15 N3 N2 2.2(6) . . . . ?
C4 C15 N3 N2 179.3(5) . . . . ?
C16 C15 N3 C17 -178.6(5) . . . . ?
C4 C15 N3 C17 -1.6(8) . . . . ?
C18 C17 N3 N2 -62.7(6) . . . . ?
C18 C17 N3 C15 118.2(6) . . . . ?
O2 C1 O1 C4 -92.8(5) . . . . ?
C2 C1 O1 C4 22.2(5) . . . . ?
C15 C4 O1 C1 -165.2(4) . . . . ?
C3 C4 O1 C1 -38.7(5) . . . . ?
O3 C5 O2 C1 -24.7(6) . . . . ?
C7 C5 O2 C1 95.7(6) . . . . ?
C6 C5 O2 C1 -141.3(5) . . . . ?
O1 C1 O2 C5 126.5(5) . . . . ?
C2 C1 O2 C5 10.4(6) . . . . ?
O2 C5 O3 C2 29.9(6) . . . . ?
C7 C5 O3 C2 -88.1(6) . . . . ?
C6 C5 O3 C2 146.0(5) . . . . ?
C1 C2 O3 C5 -22.7(5) . . . . ?
C3 C2 O3 C5 -132.2(5) . . . . ?
C4 C3 O4 C8 153.6(5) . . . . ?
C2 C3 O4 C8 -90.0(6) . . . . ?
C9 C8 O4 C3 153.9(5) . . . . ?
O8 C21 O5 C18 -99.0(4) . . . . ?
C20 C21 O5 C18 15.9(5) . . . . ?
C17 C18 O5 C21 -156.8(4) . . . . ?
C19 C18 O5 C21 -35.3(5) . . . . ?
C19 C20 O7 C22 -136.1(5) . . . . ?
C21 C20 O7 C22 -26.3(5) . . . . ?
O8 C22 O7 C20 28.3(5) . . . . ?
C23 C22 O7 C20 144.6(5) . . . . ?
C24 C22 O7 C20 -89.8(5) . . . . ?
O5 C21 O8 C22 118.6(5) . . . . ?
C20 C21 O8 C22 2.6(6) . . . . ?
O7 C22 O8 C21 -18.5(6) . . . . ?
C23 C22 O8 C21 -133.7(5) . . . . ?
C24 C22 O8 C21 100.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 1026264'
