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

#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O6'
_chemical_formula_weight         371.38

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.5637(11)
_cell_length_b                   12.141(2)
_cell_length_c                   13.461(3)
_cell_angle_alpha                71.91(3)
_cell_angle_beta                 87.24(3)
_cell_angle_gamma                82.88(3)
_cell_volume                     857.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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            8688
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_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         1.59
_diffrn_reflns_theta_max         27.92
_reflns_number_total             4045
_reflns_number_gt                2956
_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)+(0.0745P)²+0.0413P] 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         4045
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_restrained_S_all      0.902
_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
C1 C 0.9728(2) 0.42733(10) 0.65148(9) 0.0122(2) Uani 1 1 d . . .
C2 C 1.1186(2) 0.50566(10) 0.66500(9) 0.0149(2) Uani 1 1 d . . .
H2 H 1.0963 0.5856 0.6245 0.018 Uiso 1 1 calc R . .
C3 C 1.2986(2) 0.46377(11) 0.73957(9) 0.0177(3) Uani 1 1 d . . .
H3 H 1.4000 0.5161 0.7509 0.021 Uiso 1 1 calc R . .
C4 C 1.3332(2) 0.34657(11) 0.79798(9) 0.0168(3) Uani 1 1 d . . .
H4 H 1.4554 0.3200 0.8497 0.020 Uiso 1 1 calc R . .
C5 C 1.1897(2) 0.26787(10) 0.78122(9) 0.0151(2) Uani 1 1 d . . .
H5 H 1.2156 0.1874 0.8199 0.018 Uiso 1 1 calc R . .
C6 C 1.0090(2) 0.30888(10) 0.70733(8) 0.0123(2) Uani 1 1 d . . .
C7 C 0.82575(19) 0.24786(10) 0.67254(9) 0.0122(2) Uani 1 1 d . . .
H7 H 0.7139 0.2176 0.7326 0.015 Uiso 1 1 calc R . .
C8 C 0.6845(2) 0.34797(10) 0.58961(9) 0.0129(2) Uani 1 1 d . . .
C9 C 0.93394(19) 0.14525(10) 0.63356(9) 0.0125(2) Uani 1 1 d . . .
H9 H 1.0429 0.0897 0.6884 0.015 Uiso 1 1 calc R . .
C10 C 1.0769(2) 0.18293(10) 0.52985(9) 0.0140(2) Uani 1 1 d . . .
H10A H 1.1019 0.2663 0.5108 0.017 Uiso 1 1 calc R . .
H10B H 1.2366 0.1355 0.5348 0.017 Uiso 1 1 calc R . .
C11 C 0.9210(2) 0.16206(10) 0.45204(9) 0.0136(2) Uani 1 1 d . . .
C12 C 0.9334(2) 0.19274(10) 0.34814(9) 0.0163(2) Uani 1 1 d . . .
H12 H 0.8128 0.1735 0.3108 0.020 Uiso 1 1 calc R . .
C13 C 1.1307(2) 0.25582(10) 0.29062(9) 0.0165(3) Uani 1 1 d . . .
C14 C 1.2739(2) 0.35141(12) 0.12025(10) 0.0241(3) Uani 1 1 d . . .
H14A H 1.2775 0.3384 0.0511 0.029 Uiso 1 1 calc R . .
H14B H 1.4359 0.3231 0.1518 0.029 Uiso 1 1 calc R . .
C15 C 1.2185(2) 0.47984(12) 0.10621(10) 0.0235(3) Uani 1 1 d . . .
H15A H 1.0526 0.5064 0.0810 0.035 Uiso 1 1 calc R . .
H15B H 1.3322 0.5228 0.0552 0.035 Uiso 1 1 calc R . .
H15C H 1.2348 0.4939 0.1733 0.035 Uiso 1 1 calc R . .
C16 C 0.7432(2) 0.08094(10) 0.60872(9) 0.0126(2) Uani 1 1 d . . .
C17 C 0.5893(2) 0.01242(10) 0.67052(9) 0.0144(2) Uani 1 1 d . . .
H17 H 0.4837 -0.0232 0.6397 0.017 Uiso 1 1 calc R . .
C18 C 0.5782(2) -0.00931(10) 0.78307(9) 0.0153(2) Uani 1 1 d . . .
C19 C 0.3674(2) -0.09843(12) 0.93839(9) 0.0209(3) Uani 1 1 d . . .
H19A H 0.3237 -0.0246 0.9551 0.025 Uiso 1 1 calc R . .
H19B H 0.5199 -0.1377 0.9746 0.025 Uiso 1 1 calc R . .
C20 C 0.1687(2) -0.17573(12) 0.97353(10) 0.0238(3) Uani 1 1 d . . .
H20A H 0.0176 -0.1352 0.9387 0.036 Uiso 1 1 calc R . .
H20B H 0.1465 -0.1945 1.0494 0.036 Uiso 1 1 calc R . .
H20C H 0.2123 -0.2479 0.9554 0.036 Uiso 1 1 calc R . .
N1 N 0.77848(17) 0.44808(8) 0.58299(7) 0.0135(2) Uani 1 1 d . . .
H1A H 0.7243 0.5172 0.5410 0.016 Uiso 1 1 calc R . .
O1 O 0.51640(14) 0.33960(7) 0.53811(6) 0.01669(19) Uani 1 1 d . . .
O2 O 0.74001(14) 0.09669(7) 0.50312(6) 0.01509(19) Uani 1 1 d . . .
O3 O 1.30227(15) 0.27940(8) 0.32807(7) 0.0216(2) Uani 1 1 d . . .
O4 O 1.09466(17) 0.28589(8) 0.18650(7) 0.0236(2) Uani 1 1 d . . .
O5 O 0.70595(16) 0.02617(8) 0.83437(7) 0.0199(2) Uani 1 1 d . . .
O6 O 0.39876(15) -0.07484(8) 0.82618(6) 0.0182(2) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3815(16) . ?
C1 C6 1.3947(17) . ?
C1 N1 1.4023(15) . ?
C2 C3 1.3865(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3899(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3933(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3832(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5020(16) . ?
C7 C8 1.5317(16) . ?
C7 C9 1.5425(16) . ?
C7 H7 1.0000 . ?
C8 O1 1.2227(14) . ?
C8 N1 1.3582(15) . ?
C9 C16 1.4995(16) . ?
C9 C10 1.5420(16) . ?
C9 H9 1.0000 . ?
C10 C11 1.4902(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.3317(17) . ?
C11 O2 1.3815(14) . ?
C12 C13 1.4658(17) . ?
C12 H12 0.9500 . ?
C13 O3 1.2047(15) . ?
C13 O4 1.3524(15) . ?
C14 O4 1.4467(16) . ?
C14 C15 1.5051(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3401(16) . ?
C16 O2 1.3750(14) . ?
C17 C18 1.4545(17) . ?
C17 H17 0.9500 . ?
C18 O5 1.2148(15) . ?
C18 O6 1.3494(14) . ?
C19 O6 1.4533(15) . ?
C19 C20 1.5027(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 H1A 0.8800 . ?

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
C2 C1 C6 121.84(11) . . ?
C2 C1 N1 128.68(11) . . ?
C6 C1 N1 109.46(10) . . ?
C1 C2 C3 117.82(11) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C2 C3 C4 121.13(12) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.43(11) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 118.86(11) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 119.85(11) . . ?
C5 C6 C7 131.60(11) . . ?
C1 C6 C7 108.54(10) . . ?
C6 C7 C8 102.42(9) . . ?
C6 C7 C9 114.79(9) . . ?
C8 C7 C9 114.19(9) . . ?
C6 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C9 C7 H7 108.4 . . ?
O1 C8 N1 125.77(11) . . ?
O1 C8 C7 126.14(11) . . ?
N1 C8 C7 108.09(10) . . ?
C16 C9 C10 103.05(9) . . ?
C16 C9 C7 112.60(9) . . ?
C10 C9 C7 113.74(10) . . ?
C16 C9 H9 109.1 . . ?
C10 C9 H9 109.1 . . ?
C7 C9 H9 109.1 . . ?
C11 C10 C9 104.13(9) . . ?
C11 C10 H10A 110.9 . . ?
C9 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C12 C11 O2 118.79(11) . . ?
C12 C11 C10 131.38(11) . . ?
O2 C11 C10 109.81(10) . . ?
C11 C12 C13 120.92(11) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
O3 C13 O4 123.27(11) . . ?
O3 C13 C12 126.42(11) . . ?
O4 C13 C12 110.31(11) . . ?
O4 C14 C15 111.26(11) . . ?
O4 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
O4 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 O2 118.18(11) . . ?
C17 C16 C9 131.38(11) . . ?
O2 C16 C9 110.42(10) . . ?
C16 C17 C18 122.33(11) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
O5 C18 O6 122.52(11) . . ?
O5 C18 C17 126.79(11) . . ?
O6 C18 C17 110.68(10) . . ?
O6 C19 C20 107.84(11) . . ?
O6 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
O6 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N1 C1 111.47(10) . . ?
C8 N1 H1A 124.3 . . ?
C1 N1 H1A 124.3 . . ?
C16 O2 C11 110.77(9) . . ?
C13 O4 C14 116.07(10) . . ?
C18 O6 C19 115.01(10) . . ?

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
C6 C1 C2 C3 -2.51(16) . . . . ?
N1 C1 C2 C3 179.04(10) . . . . ?
C1 C2 C3 C4 0.74(16) . . . . ?
C2 C3 C4 C5 1.27(17) . . . . ?
C3 C4 C5 C6 -1.51(17) . . . . ?
C4 C5 C6 C1 -0.22(16) . . . . ?
C4 C5 C6 C7 -179.23(11) . . . . ?
C2 C1 C6 C5 2.29(16) . . . . ?
N1 C1 C6 C5 -179.00(9) . . . . ?
C2 C1 C6 C7 -178.49(10) . . . . ?
N1 C1 C6 C7 0.22(12) . . . . ?
C5 C6 C7 C8 179.43(11) . . . . ?
C1 C6 C7 C8 0.34(11) . . . . ?
C5 C6 C7 C9 -56.24(16) . . . . ?
C1 C6 C7 C9 124.67(10) . . . . ?
C6 C7 C8 O1 179.14(10) . . . . ?
C9 C7 C8 O1 54.41(15) . . . . ?
C6 C7 C8 N1 -0.80(11) . . . . ?
C9 C7 C8 N1 -125.52(10) . . . . ?
C6 C7 C9 C16 174.97(9) . . . . ?
C8 C7 C9 C16 -67.18(13) . . . . ?
C6 C7 C9 C10 -68.27(13) . . . . ?
C8 C7 C9 C10 49.58(13) . . . . ?
C16 C9 C10 C11 13.03(11) . . . . ?
C7 C9 C10 C11 -109.17(11) . . . . ?
C9 C10 C11 C12 169.49(12) . . . . ?
C9 C10 C11 O2 -12.22(12) . . . . ?
O2 C11 C12 C13 -176.19(10) . . . . ?
C10 C11 C12 C13 2.0(2) . . . . ?
C11 C12 C13 O3 4.80(19) . . . . ?
C11 C12 C13 O4 -174.93(11) . . . . ?
C10 C9 C16 C17 167.94(12) . . . . ?
C7 C9 C16 C17 -69.10(16) . . . . ?
C10 C9 C16 O2 -10.28(11) . . . . ?
C7 C9 C16 O2 112.68(10) . . . . ?
O2 C16 C17 C18 -179.77(10) . . . . ?
C9 C16 C17 C18 2.13(19) . . . . ?
C16 C17 C18 O5 -2.77(19) . . . . ?
C16 C17 C18 O6 176.12(10) . . . . ?
O1 C8 N1 C1 -178.94(10) . . . . ?
C7 C8 N1 C1 0.99(12) . . . . ?
C2 C1 N1 C8 177.81(11) . . . . ?
C6 C1 N1 C8 -0.79(12) . . . . ?
C17 C16 O2 C11 -175.48(10) . . . . ?
C9 C16 O2 C11 3.00(12) . . . . ?
C12 C11 O2 C16 -175.31(10) . . . . ?
C10 C11 O2 C16 6.15(12) . . . . ?
O3 C13 O4 C14 -1.18(18) . . . . ?
C12 C13 O4 C14 178.56(10) . . . . ?
C15 C14 O4 C13 -84.66(14) . . . . ?
O5 C18 O6 C19 0.83(16) . . . . ?
C17 C18 O6 C19 -178.12(10) . . . . ?
C20 C19 O6 C18 -177.75(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.92
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 1015270'
#######################################################################
#
#                 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_n140628a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N O6'
_chemical_formula_weight         433.44

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                   9.5427(19)
_cell_length_b                   9.677(2)
_cell_length_c                   11.933(2)
_cell_angle_alpha                93.455(4)
_cell_angle_beta                 99.378(4)
_cell_angle_gamma                97.885(4)
_cell_volume                     1073.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3055
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.17

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9829
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            5931
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3757
_reflns_number_gt                3232
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0455P)²+1.8208P] 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_number_reflns         3757
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.057
_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 0.2645(2) -0.08721(18) 0.86411(15) 0.0230(4) Uani 1 1 d . . .
O2 O 0.3585(2) -0.13161(19) 0.70704(16) 0.0256(4) Uani 1 1 d . . .
O3 O -0.09844(19) 0.33569(19) 0.51180(15) 0.0246(4) Uani 1 1 d . . .
O4 O -0.11876(18) 0.40918(18) 0.33491(14) 0.0205(4) Uani 1 1 d . . .
O5 O 0.45125(19) 0.31767(18) 0.53035(14) 0.0222(4) Uani 1 1 d . . .
O6 O 0.10302(18) 0.15134(18) 0.55293(14) 0.0199(4) Uani 1 1 d . . .
N1 N 0.4085(2) 0.4073(2) 0.35571(17) 0.0184(5) Uani 1 1 d . . .
H1 H 0.4413 0.4959 0.3777 0.022 Uiso 1 1 calc R . .
C1 C 0.3036(3) -0.2116(3) 1.0314(2) 0.0214(6) Uani 1 1 d . . .
C2 C 0.4062(3) -0.1795(3) 1.1297(2) 0.0279(6) Uani 1 1 d . . .
H2 H 0.5021 -0.1426 1.1242 0.033 Uiso 1 1 calc R . .
C3 C 0.3698(4) -0.2008(3) 1.2358(2) 0.0384(8) Uani 1 1 d . . .
H3 H 0.4407 -0.1791 1.3026 0.046 Uiso 1 1 calc R . .
C4 C 0.2313(4) -0.2533(3) 1.2441(3) 0.0440(9) Uani 1 1 d . . .
H4 H 0.2060 -0.2674 1.3167 0.053 Uiso 1 1 calc R . .
C5 C 0.1274(4) -0.2860(4) 1.1458(3) 0.0421(8) Uani 1 1 d . . .
H5 H 0.0315 -0.3224 1.1516 0.050 Uiso 1 1 calc R . .
C6 C 0.1641(3) -0.2653(3) 1.0401(2) 0.0289(6) Uani 1 1 d . . .
H6 H 0.0934 -0.2880 0.9732 0.035 Uiso 1 1 calc R . .
C7 C 0.3455(3) -0.1909(3) 0.9169(2) 0.0281(6) Uani 1 1 d . . .
H7A H 0.4499 -0.1577 0.9258 0.034 Uiso 1 1 calc R . .
H7B H 0.3233 -0.2805 0.8684 0.034 Uiso 1 1 calc R . .
C8 C 0.2814(3) -0.0686(3) 0.7557(2) 0.0194(5) Uani 1 1 d . . .
C9 C 0.1946(3) 0.0326(3) 0.7068(2) 0.0202(5) Uani 1 1 d . . .
H9 H 0.1388 0.0785 0.7521 0.024 Uiso 1 1 calc R . .
C10 C 0.1930(3) 0.0613(2) 0.5987(2) 0.0179(5) Uani 1 1 d . . .
C11 C 0.1169(3) 0.1710(2) 0.4414(2) 0.0175(5) Uani 1 1 d . . .
C12 C 0.2214(3) 0.0813(2) 0.4042(2) 0.0180(5) Uani 1 1 d . . .
H12 H 0.1676 0.0080 0.3441 0.022 Uiso 1 1 calc R . .
C13 C 0.2731(3) 0.0096(3) 0.5114(2) 0.0214(6) Uani 1 1 d . . .
H13A H 0.2506 -0.0935 0.4968 0.026 Uiso 1 1 calc R . .
H13B H 0.3780 0.0359 0.5366 0.026 Uiso 1 1 calc R . .
C14 C 0.0435(3) 0.2564(3) 0.3802(2) 0.0195(5) Uani 1 1 d . . .
H14 H 0.0614 0.2669 0.3049 0.023 Uiso 1 1 calc R . .
C15 C -0.0625(3) 0.3355(3) 0.4191(2) 0.0187(5) Uani 1 1 d . . .
C16 C -0.2293(3) 0.4878(3) 0.3635(2) 0.0222(6) Uani 1 1 d . . .
H16A H -0.1920 0.5508 0.4336 0.027 Uiso 1 1 calc R . .
H16B H -0.3137 0.4232 0.3766 0.027 Uiso 1 1 calc R . .
C17 C -0.2705(3) 0.5716(3) 0.2647(2) 0.0256(6) Uani 1 1 d . . .
H17A H -0.1847 0.6301 0.2491 0.038 Uiso 1 1 calc R . .
H17B H -0.3399 0.6313 0.2834 0.038 Uiso 1 1 calc R . .
H17C H -0.3138 0.5079 0.1973 0.038 Uiso 1 1 calc R . .
C18 C 0.3437(3) 0.1652(2) 0.3558(2) 0.0167(5) Uani 1 1 d . . .
H18 H 0.4219 0.1063 0.3547 0.020 Uiso 1 1 calc R . .
C19 C 0.3056(3) 0.2121(2) 0.2385(2) 0.0167(5) Uani 1 1 d . . .
C20 C 0.2419(3) 0.1372(3) 0.1361(2) 0.0225(6) Uani 1 1 d . . .
H20 H 0.2108 0.0393 0.1328 0.027 Uiso 1 1 calc R . .
C21 C 0.2246(3) 0.2086(3) 0.0383(2) 0.0288(6) Uani 1 1 d . . .
H21 H 0.1813 0.1590 -0.0328 0.035 Uiso 1 1 calc R . .
C22 C 0.2702(3) 0.3517(3) 0.0438(2) 0.0310(7) Uani 1 1 d . . .
H22 H 0.2571 0.3986 -0.0240 0.037 Uiso 1 1 calc R . .
C23 C 0.3347(3) 0.4286(3) 0.1462(2) 0.0253(6) Uani 1 1 d . . .
H23 H 0.3667 0.5264 0.1495 0.030 Uiso 1 1 calc R . .
C24 C 0.3501(3) 0.3562(3) 0.2425(2) 0.0175(5) Uani 1 1 d . . .
C25 C 0.4080(3) 0.3030(2) 0.4268(2) 0.0168(5) 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 C8 1.349(3) . ?
O1 C7 1.460(3) . ?
O2 C8 1.212(3) . ?
O3 C15 1.210(3) . ?
O4 C15 1.350(3) . ?
O4 C16 1.454(3) . ?
O5 C25 1.230(3) . ?
O6 C10 1.380(3) . ?
O6 C11 1.381(3) . ?
N1 C25 1.358(3) . ?
N1 C24 1.406(3) . ?
N1 H1 0.8800 . ?
C1 C6 1.384(4) . ?
C1 C2 1.389(4) . ?
C1 C7 1.502(4) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.457(4) . ?
C9 C10 1.334(4) . ?
C9 H9 0.9500 . ?
C10 C13 1.490(4) . ?
C11 C14 1.330(4) . ?
C11 C12 1.510(3) . ?
C12 C13 1.535(3) . ?
C12 C18 1.540(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.466(4) . ?
C14 H14 0.9500 . ?
C16 C17 1.501(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.501(3) . ?
C18 C25 1.530(3) . ?
C18 H18 1.0000 . ?
C19 C20 1.384(3) . ?
C19 C24 1.397(3) . ?
C20 C21 1.390(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.395(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C7 114.14(19) . . ?
C15 O4 C16 114.50(19) . . ?
C10 O6 C11 111.16(19) . . ?
C25 N1 C24 111.6(2) . . ?
C25 N1 H1 124.2 . . ?
C24 N1 H1 124.2 . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 C7 120.7(2) . . ?
C2 C1 C7 119.9(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 C1 108.0(2) . . ?
O1 C7 H7A 110.1 . . ?
C1 C7 H7A 110.1 . . ?
O1 C7 H7B 110.1 . . ?
C1 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O2 C8 O1 122.8(2) . . ?
O2 C8 C9 125.8(2) . . ?
O1 C8 C9 111.5(2) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 O6 118.9(2) . . ?
C9 C10 C13 130.8(2) . . ?
O6 C10 C13 110.3(2) . . ?
C14 C11 O6 122.2(2) . . ?
C14 C11 C12 127.9(2) . . ?
O6 C11 C12 109.9(2) . . ?
C11 C12 C13 103.9(2) . . ?
C11 C12 C18 113.14(19) . . ?
C13 C12 C18 113.8(2) . . ?
C11 C12 H12 108.6 . . ?
C13 C12 H12 108.6 . . ?
C18 C12 H12 108.6 . . ?
C10 C13 C12 104.7(2) . . ?
C10 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
C10 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
C11 C14 C15 125.5(2) . . ?
C11 C14 H14 117.2 . . ?
C15 C14 H14 117.2 . . ?
O3 C15 O4 123.4(2) . . ?
O3 C15 C14 126.5(2) . . ?
O4 C15 C14 110.1(2) . . ?
O4 C16 C17 107.2(2) . . ?
O4 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
O4 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C25 102.52(19) . . ?
C19 C18 C12 116.6(2) . . ?
C25 C18 C12 113.21(19) . . ?
C19 C18 H18 108.0 . . ?
C25 C18 H18 108.0 . . ?
C12 C18 H18 108.0 . . ?
C20 C19 C24 120.2(2) . . ?
C20 C19 C18 131.1(2) . . ?
C24 C19 C18 108.6(2) . . ?
C19 C20 C21 118.5(2) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 121.8(3) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C22 117.0(2) . . ?
C24 C23 H23 121.5 . . ?
C22 C23 H23 121.5 . . ?
C23 C24 C19 122.0(2) . . ?
C23 C24 N1 128.9(2) . . ?
C19 C24 N1 109.1(2) . . ?
O5 C25 N1 125.6(2) . . ?
O5 C25 C18 126.3(2) . . ?
N1 C25 C18 108.1(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
C6 C1 C2 C3 0.0(4) . . . . ?
C7 C1 C2 C3 -178.7(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C7 C1 C6 C5 179.0(3) . . . . ?
C8 O1 C7 C1 -173.8(2) . . . . ?
C6 C1 C7 O1 63.4(3) . . . . ?
C2 C1 C7 O1 -117.9(3) . . . . ?
C7 O1 C8 O2 -0.8(3) . . . . ?
C7 O1 C8 C9 178.2(2) . . . . ?
O2 C8 C9 C10 1.3(4) . . . . ?
O1 C8 C9 C10 -177.6(2) . . . . ?
C8 C9 C10 O6 176.2(2) . . . . ?
C8 C9 C10 C13 -2.6(4) . . . . ?
C11 O6 C10 C9 179.0(2) . . . . ?
C11 O6 C10 C13 -2.0(3) . . . . ?
C10 O6 C11 C14 -178.3(2) . . . . ?
C10 O6 C11 C12 2.8(3) . . . . ?
C14 C11 C12 C13 178.9(2) . . . . ?
O6 C11 C12 C13 -2.3(2) . . . . ?
C14 C11 C12 C18 55.0(3) . . . . ?
O6 C11 C12 C18 -126.2(2) . . . . ?
C9 C10 C13 C12 179.3(3) . . . . ?
O6 C10 C13 C12 0.5(3) . . . . ?
C11 C12 C13 C10 1.1(2) . . . . ?
C18 C12 C13 C10 124.5(2) . . . . ?
O6 C11 C14 C15 -2.1(4) . . . . ?
C12 C11 C14 C15 176.5(2) . . . . ?
C16 O4 C15 O3 -1.1(3) . . . . ?
C16 O4 C15 C14 177.9(2) . . . . ?
C11 C14 C15 O3 0.4(4) . . . . ?
C11 C14 C15 O4 -178.7(2) . . . . ?
C15 O4 C16 C17 175.5(2) . . . . ?
C11 C12 C18 C19 -74.5(3) . . . . ?
C13 C12 C18 C19 167.3(2) . . . . ?
C11 C12 C18 C25 44.1(3) . . . . ?
C13 C12 C18 C25 -74.2(3) . . . . ?
C25 C18 C19 C20 -179.2(3) . . . . ?
C12 C18 C19 C20 -54.9(4) . . . . ?
C25 C18 C19 C24 2.9(3) . . . . ?
C12 C18 C19 C24 127.1(2) . . . . ?
C24 C19 C20 C21 0.4(4) . . . . ?
C18 C19 C20 C21 -177.4(3) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C21 C22 C23 0.2(5) . . . . ?
C21 C22 C23 C24 -0.7(4) . . . . ?
C22 C23 C24 C19 1.0(4) . . . . ?
C22 C23 C24 N1 -178.9(3) . . . . ?
C20 C19 C24 C23 -0.9(4) . . . . ?
C18 C19 C24 C23 177.3(2) . . . . ?
C20 C19 C24 N1 179.0(2) . . . . ?
C18 C19 C24 N1 -2.8(3) . . . . ?
C25 N1 C24 C23 -178.6(3) . . . . ?
C25 N1 C24 C19 1.5(3) . . . . ?
C24 N1 C25 O5 -179.2(2) . . . . ?
C24 N1 C25 C18 0.4(3) . . . . ?
C19 C18 C25 O5 177.6(2) . . . . ?
C12 C18 C25 O5 51.2(3) . . . . ?
C19 C18 C25 N1 -2.0(2) . . . . ?
C12 C18 C25 N1 -128.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 1015271'
#######################################################################
#
#                 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_n140417a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N O6'
_chemical_formula_weight         447.47

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                   12.0466(11)
_cell_length_b                   11.5265(10)
_cell_length_c                   16.5292(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.315(2)
_cell_angle_gamma                90.00
_cell_volume                     2250.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4236
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.06

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9833
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            12738
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3949
_reflns_number_gt                3146
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0531P)²+0.2899P] 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_number_reflns         3949
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N1 N 0.01522(13) 0.95746(13) 0.15729(9) 0.0236(4) Uani 1 1 d . . .
O1 O 0.03105(11) 0.76730(11) 0.20175(7) 0.0284(3) Uani 1 1 d . . .
O2 O 0.26243(10) 0.62588(10) 0.23554(6) 0.0198(3) Uani 1 1 d . . .
O3 O 0.41667(11) 0.89548(11) 0.39269(7) 0.0252(3) Uani 1 1 d . . .
O4 O 0.43997(10) 0.75981(10) 0.49235(7) 0.0217(3) Uani 1 1 d . . .
O5 O 0.18060(11) 0.66650(11) -0.02684(7) 0.0255(3) Uani 1 1 d . . .
O6 O 0.13077(12) 0.47808(11) -0.02392(7) 0.0298(3) Uani 1 1 d . . .
C1 C 0.07155(16) 1.03074(16) 0.11064(10) 0.0235(4) Uani 1 1 d . . .
C2 C 0.15330(16) 0.96735(15) 0.08023(10) 0.0214(4) Uani 1 1 d . . .
C3 C 0.22091(17) 1.02166(17) 0.03367(10) 0.0280(5) Uani 1 1 d . . .
H3 H 0.2758 0.9803 0.0134 0.034 Uiso 1 1 calc R . .
C4 C 0.2055(2) 1.14024(18) 0.01744(12) 0.0368(5) Uani 1 1 d . . .
H4 H 0.2506 1.1783 -0.0138 0.044 Uiso 1 1 calc R . .
C5 C 0.1237(2) 1.20100(18) 0.04762(12) 0.0396(6) Uani 1 1 d . . .
H5 H 0.1143 1.2797 0.0358 0.048 Uiso 1 1 calc R . .
C6 C 0.05469(18) 1.14794(17) 0.09540(11) 0.0320(5) Uani 1 1 d . . .
H6 H 0.0000 1.1894 0.1160 0.038 Uiso 1 1 calc R . .
C7 C 0.05783(15) 0.84694(15) 0.16094(10) 0.0202(4) Uani 1 1 d . . .
C8 C 0.14346(15) 0.84241(14) 0.10387(10) 0.0180(4) Uani 1 1 d . . .
H8 H 0.1076 0.8005 0.0539 0.022 Uiso 1 1 calc R . .
C9 C -0.07917(17) 0.99254(18) 0.19429(12) 0.0320(5) Uani 1 1 d . . .
H9A H -0.1433 1.0100 0.1516 0.048 Uiso 1 1 calc R . .
H9B H -0.0585 1.0602 0.2277 0.048 Uiso 1 1 calc R . .
H9C H -0.0981 0.9307 0.2280 0.048 Uiso 1 1 calc R . .
C10 C 0.25405(14) 0.77914(14) 0.13973(10) 0.0171(4) Uani 1 1 d . . .
H10 H 0.3067 0.7880 0.1019 0.021 Uiso 1 1 calc R . .
C11 C 0.23571(15) 0.65192(15) 0.15294(9) 0.0173(4) Uani 1 1 d . . .
C12 C 0.30848(15) 0.72008(14) 0.28143(10) 0.0178(4) Uani 1 1 d . . .
C13 C 0.31191(15) 0.82186(15) 0.22612(10) 0.0182(4) Uani 1 1 d . . .
H13A H 0.3894 0.8452 0.2266 0.022 Uiso 1 1 calc R . .
H13B H 0.2712 0.8872 0.2432 0.022 Uiso 1 1 calc R . .
C14 C 0.34504(15) 0.70506(15) 0.36218(10) 0.0206(4) Uani 1 1 d . . .
H14 H 0.3342 0.6338 0.3858 0.025 Uiso 1 1 calc R . .
C15 C 0.40152(15) 0.79769(15) 0.41414(10) 0.0193(4) Uani 1 1 d . . .
C16 C 0.49625(16) 0.84772(16) 0.54797(10) 0.0233(4) Uani 1 1 d . . .
H16A H 0.4439 0.9102 0.5525 0.028 Uiso 1 1 calc R . .
H16B H 0.5594 0.8796 0.5268 0.028 Uiso 1 1 calc R . .
C17 C 0.53819(15) 0.79440(16) 0.63125(10) 0.0201(4) Uani 1 1 d . . .
C18 C 0.57360(16) 0.67957(17) 0.64033(11) 0.0264(4) Uani 1 1 d . . .
H18 H 0.5671 0.6320 0.5942 0.032 Uiso 1 1 calc R . .
C19 C 0.61867(17) 0.63566(18) 0.71815(12) 0.0323(5) Uani 1 1 d . . .
H19 H 0.6418 0.5586 0.7241 0.039 Uiso 1 1 calc R . .
C20 C 0.62912(17) 0.70638(19) 0.78685(12) 0.0323(5) Uani 1 1 d . . .
H20 H 0.6602 0.6771 0.8388 0.039 Uiso 1 1 calc R . .
C21 C 0.59365(17) 0.82010(18) 0.77846(11) 0.0293(5) Uani 1 1 d . . .
H21 H 0.6005 0.8675 0.8247 0.035 Uiso 1 1 calc R . .
C22 C 0.54768(16) 0.86370(16) 0.70091(10) 0.0235(4) Uani 1 1 d . . .
H22 H 0.5229 0.9403 0.6955 0.028 Uiso 1 1 calc R . .
C23 C 0.20107(15) 0.56447(15) 0.10092(10) 0.0202(4) Uani 1 1 d . . .
H23 H 0.1955 0.4909 0.1228 0.024 Uiso 1 1 calc R . .
C24 C 0.17143(15) 0.57860(15) 0.01122(10) 0.0192(4) Uani 1 1 d . . .
C25 C 0.09687(17) 0.47497(17) -0.11335(10) 0.0281(5) Uani 1 1 d . . .
H25A H 0.0845 0.5533 -0.1346 0.034 Uiso 1 1 calc R . .
H25B H 0.0265 0.4324 -0.1288 0.034 Uiso 1 1 calc R . .
C26 C 0.18682(17) 0.41786(18) -0.14975(11) 0.0306(5) Uani 1 1 d . . .
H26A H 0.2555 0.4622 -0.1364 0.046 Uiso 1 1 calc R . .
H26B H 0.1629 0.4138 -0.2086 0.046 Uiso 1 1 calc R . .
H26C H 0.2000 0.3409 -0.1277 0.046 Uiso 1 1 calc 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
N1 C7 1.370(2) . ?
N1 C1 1.405(2) . ?
N1 C9 1.450(2) . ?
O1 C7 1.219(2) . ?
O2 C11 1.3731(19) . ?
O2 C12 1.377(2) . ?
O3 C15 1.206(2) . ?
O4 C15 1.357(2) . ?
O4 C16 1.445(2) . ?
O5 C24 1.209(2) . ?
O6 C24 1.345(2) . ?
O6 C25 1.455(2) . ?
C1 C6 1.382(3) . ?
C1 C2 1.397(3) . ?
C2 C3 1.376(3) . ?
C2 C8 1.503(2) . ?
C3 C4 1.398(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.529(2) . ?
C8 C10 1.532(2) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.505(2) . ?
C10 C13 1.542(2) . ?
C10 H10 0.9800 . ?
C11 C23 1.337(2) . ?
C12 C14 1.332(2) . ?
C12 C13 1.493(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.453(2) . ?
C14 H14 0.9300 . ?
C16 C17 1.502(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.387(2) . ?
C17 C18 1.390(3) . ?
C18 C19 1.390(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.464(2) . ?
C23 H23 0.9300 . ?
C25 C26 1.492(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C7 N1 C1 111.47(15) . . ?
C7 N1 C9 123.95(16) . . ?
C1 N1 C9 124.53(15) . . ?
C11 O2 C12 111.46(13) . . ?
C15 O4 C16 114.23(13) . . ?
C24 O6 C25 117.78(14) . . ?
C6 C1 C2 122.33(18) . . ?
C6 C1 N1 128.18(18) . . ?
C2 C1 N1 109.48(15) . . ?
C3 C2 C1 119.98(17) . . ?
C3 C2 C8 131.82(17) . . ?
C1 C2 C8 108.10(15) . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.97(19) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 116.7(2) . . ?
C1 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
O1 C7 N1 125.93(16) . . ?
O1 C7 C8 126.81(16) . . ?
N1 C7 C8 107.26(14) . . ?
C2 C8 C7 102.99(14) . . ?
C2 C8 C10 116.72(15) . . ?
C7 C8 C10 114.72(13) . . ?
C2 C8 H8 107.3 . . ?
C7 C8 H8 107.3 . . ?
C10 C8 H8 107.3 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 112.24(14) . . ?
C11 C10 C13 103.25(13) . . ?
C8 C10 C13 114.01(14) . . ?
C11 C10 H10 109.0 . . ?
C8 C10 H10 109.0 . . ?
C13 C10 H10 109.0 . . ?
C23 C11 O2 117.21(15) . . ?
C23 C11 C10 132.61(15) . . ?
O2 C11 C10 110.17(13) . . ?
C14 C12 O2 117.87(15) . . ?
C14 C12 C13 132.24(16) . . ?
O2 C12 C13 109.81(13) . . ?
C12 C13 C10 104.74(13) . . ?
C12 C13 H13A 110.8 . . ?
C10 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
C10 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
C12 C14 C15 121.41(16) . . ?
C12 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
O3 C15 O4 122.53(16) . . ?
O3 C15 C14 126.38(16) . . ?
O4 C15 C14 111.06(15) . . ?
O4 C16 C17 109.13(14) . . ?
O4 C16 H16A 109.9 . . ?
C17 C16 H16A 109.9 . . ?
O4 C16 H16B 109.9 . . ?
C17 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C22 C17 C18 119.02(16) . . ?
C22 C17 C16 118.90(16) . . ?
C18 C17 C16 121.98(16) . . ?
C19 C18 C17 120.18(18) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.08(19) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.12(18) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.84(18) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C17 120.75(18) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C11 C23 C24 123.40(16) . . ?
C11 C23 H23 118.3 . . ?
C24 C23 H23 118.3 . . ?
O5 C24 O6 124.05(15) . . ?
O5 C24 C23 126.23(16) . . ?
O6 C24 C23 109.72(15) . . ?
O6 C25 C26 109.84(16) . . ?
O6 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
O6 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C7 N1 C1 C6 -177.87(18) . . . . ?
C9 N1 C1 C6 4.5(3) . . . . ?
C7 N1 C1 C2 1.3(2) . . . . ?
C9 N1 C1 C2 -176.38(16) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
N1 C1 C2 C3 -178.85(16) . . . . ?
C6 C1 C2 C8 -176.51(16) . . . . ?
N1 C1 C2 C8 4.27(19) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C8 C2 C3 C4 175.69(18) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
N1 C1 C6 C5 179.11(17) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C1 N1 C7 O1 174.46(17) . . . . ?
C9 N1 C7 O1 -7.8(3) . . . . ?
C1 N1 C7 C8 -6.17(19) . . . . ?
C9 N1 C7 C8 171.53(15) . . . . ?
C3 C2 C8 C7 176.14(18) . . . . ?
C1 C2 C8 C7 -7.49(18) . . . . ?
C3 C2 C8 C10 49.5(3) . . . . ?
C1 C2 C8 C10 -134.12(15) . . . . ?
O1 C7 C8 C2 -172.42(17) . . . . ?
N1 C7 C8 C2 8.21(17) . . . . ?
O1 C7 C8 C10 -44.5(2) . . . . ?
N1 C7 C8 C10 136.11(15) . . . . ?
C2 C8 C10 C11 -174.06(13) . . . . ?
C7 C8 C10 C11 65.36(18) . . . . ?
C2 C8 C10 C13 68.98(18) . . . . ?
C7 C8 C10 C13 -51.60(19) . . . . ?
C12 O2 C11 C23 173.34(15) . . . . ?
C12 O2 C11 C10 -5.92(18) . . . . ?
C8 C10 C11 C23 65.3(2) . . . . ?
C13 C10 C11 C23 -171.42(19) . . . . ?
C8 C10 C11 O2 -115.54(15) . . . . ?
C13 C10 C11 O2 7.69(17) . . . . ?
C11 O2 C12 C14 -175.84(15) . . . . ?
C11 O2 C12 C13 1.35(18) . . . . ?
C14 C12 C13 C10 -179.81(18) . . . . ?
O2 C12 C13 C10 3.54(18) . . . . ?
C11 C10 C13 C12 -6.51(17) . . . . ?
C8 C10 C13 C12 115.54(16) . . . . ?
O2 C12 C14 C15 175.85(15) . . . . ?
C13 C12 C14 C15 -0.6(3) . . . . ?
C16 O4 C15 O3 2.4(2) . . . . ?
C16 O4 C15 C14 -179.40(14) . . . . ?
C12 C14 C15 O3 3.6(3) . . . . ?
C12 C14 C15 O4 -174.61(16) . . . . ?
C15 O4 C16 C17 -178.05(14) . . . . ?
O4 C16 C17 C22 -151.29(16) . . . . ?
O4 C16 C17 C18 32.3(2) . . . . ?
C22 C17 C18 C19 -0.5(3) . . . . ?
C16 C17 C18 C19 175.84(17) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C21 C22 C17 -0.8(3) . . . . ?
C18 C17 C22 C21 1.2(3) . . . . ?
C16 C17 C22 C21 -175.34(17) . . . . ?
O2 C11 C23 C24 -179.00(15) . . . . ?
C10 C11 C23 C24 0.1(3) . . . . ?
C25 O6 C24 O5 0.6(3) . . . . ?
C25 O6 C24 C23 -179.82(15) . . . . ?
C11 C23 C24 O5 4.7(3) . . . . ?
C11 C23 C24 O6 -174.81(16) . . . . ?
C24 O6 C25 C26 101.40(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 1015272'
