# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


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#                 Cambridge Crystallographic Data Centre
#                                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 
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#  except for the purpose of generating routine backup copies 
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data_m:\101123n\work\101123nm
_database_code_depnum_ccdc_archive 'CCDC 814555'
#TrackingRef '- 101123nm.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H34 N2 O12'
_chemical_formula_weight         590.57

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   7.6651(6)
_cell_length_b                   13.1131(9)
_cell_length_c                   29.874(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3002.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8155
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      24.91

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.103
_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  '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            28176
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2797
_reflns_number_gt                2364
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0704P)^2^+0.4968P] where P=(Fo^2^+2Fc^2^)/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       0.0140(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2797
_refine_ls_number_parameters     215
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.0920(3) 0.88289(13) 0.53115(6) 0.0673(5) Uani 1 1 d . . .
H1A H 0.0129 0.8421 0.5485 0.101 Uiso 1 1 calc R . .
H1B H 0.0799 0.9532 0.5396 0.101 Uiso 1 1 calc R . .
H1C H 0.2095 0.8609 0.5366 0.101 Uiso 1 1 calc R . .
C2 C 0.06689(19) 0.77699(10) 0.46655(5) 0.0474(4) Uani 1 1 d . . .
C3 C 0.03016(19) 0.77070(11) 0.42105(5) 0.0471(3) Uani 1 1 d . . .
H3 H -0.0046 0.8288 0.4056 0.056 Uiso 1 1 calc R . .
C4 C 0.04480(17) 0.67862(11) 0.39834(4) 0.0432(3) Uani 1 1 d . . .
C5 C 0.09380(18) 0.59264(11) 0.42262(5) 0.0450(3) Uani 1 1 d . . .
C6 C 0.1296(2) 0.59833(12) 0.46761(5) 0.0523(4) Uani 1 1 d . . .
H6 H 0.1618 0.5399 0.4832 0.063 Uiso 1 1 calc R . .
C7 C 0.1178(2) 0.69060(11) 0.48976(5) 0.0523(4) Uani 1 1 d . . .
H7 H 0.1440 0.6946 0.5201 0.063 Uiso 1 1 calc R . .
C8 C -0.0237(2) 0.43481(11) 0.39930(5) 0.0522(4) Uani 1 1 d . . .
C9 C 0.0199(3) 0.33838(13) 0.37569(7) 0.0729(5) Uani 1 1 d . . .
H9A H -0.0842 0.2988 0.3716 0.109 Uiso 1 1 calc R . .
H9B H 0.1023 0.3002 0.3932 0.109 Uiso 1 1 calc R . .
H9C H 0.0699 0.3539 0.3470 0.109 Uiso 1 1 calc R . .
C10 C 0.01752(18) 0.67409(11) 0.34924(5) 0.0463(3) Uani 1 1 d . . .
C11 C 0.1184(2) 0.59632(12) 0.32215(5) 0.0515(4) Uani 1 1 d . A .
C12 C 0.4021(10) 0.5374(7) 0.3076(3) 0.0613(16) Uani 0.58 1 d PD A 1
H12A H 0.3873 0.5320 0.2754 0.074 Uiso 0.58 1 calc PR A 1
H12B H 0.3770 0.4716 0.3210 0.074 Uiso 0.58 1 calc PR A 1
C13 C 0.5822(6) 0.5708(5) 0.3188(2) 0.0903(16) Uani 0.58 1 d PD A 1
H13A H 0.5986 0.6401 0.3093 0.135 Uiso 0.58 1 calc PR A 1
H13B H 0.6648 0.5277 0.3038 0.135 Uiso 0.58 1 calc PR A 1
H13C H 0.5997 0.5662 0.3505 0.135 Uiso 0.58 1 calc PR A 1
C12' C 0.4225(16) 0.5559(11) 0.3044(5) 0.103(6) Uani 0.42 1 d PD A 2
H12C H 0.4712 0.5924 0.2790 0.123 Uiso 0.42 1 calc PR A 2
H12D H 0.3755 0.4915 0.2939 0.123 Uiso 0.42 1 calc PR A 2
C13' C 0.5576(9) 0.5387(7) 0.3391(3) 0.095(3) Uani 0.42 1 d PD A 2
H13D H 0.6098 0.6027 0.3471 0.143 Uiso 0.42 1 calc PR A 2
H13E H 0.6456 0.4938 0.3275 0.143 Uiso 0.42 1 calc PR A 2
H13F H 0.5048 0.5085 0.3650 0.143 Uiso 0.42 1 calc PR A 2
C14 C -0.1897(3) 0.80585(16) 0.26476(7) 0.0846(6) Uani 1 1 d . . .
H14A H -0.3039 0.8028 0.2779 0.127 Uiso 1 1 calc R . .
H14B H -0.1982 0.7942 0.2331 0.127 Uiso 1 1 calc R . .
H14C H -0.1398 0.8719 0.2701 0.127 Uiso 1 1 calc R . .
N1 N -0.08278(17) 0.73967(10) 0.33108(4) 0.0545(3) Uani 1 1 d . . .
O1 O 0.05281(16) 0.87179(8) 0.48489(4) 0.0610(3) Uani 1 1 d . . .
O2 O -0.15975(18) 0.45632(10) 0.41542(5) 0.0821(4) Uani 1 1 d . . .
O3 O 0.11628(14) 0.49862(7) 0.40061(3) 0.0519(3) Uani 1 1 d . . .
O4 O 0.28668(14) 0.61651(9) 0.32606(4) 0.0622(3) Uani 1 1 d D . .
O5 O 0.05510(17) 0.52771(10) 0.30132(4) 0.0696(4) Uani 1 1 d . . .
O6 O -0.08197(16) 0.72998(10) 0.28433(4) 0.0680(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0855(12) 0.0615(10) 0.0548(10) -0.0156(8) -0.0140(8) -0.0003(9)
C2 0.0514(8) 0.0443(8) 0.0464(8) -0.0047(6) -0.0004(6) -0.0032(6)
C3 0.0529(8) 0.0437(8) 0.0446(8) 0.0022(6) -0.0023(6) 0.0017(6)
C4 0.0419(7) 0.0457(8) 0.0419(7) -0.0015(5) 0.0010(5) 0.0010(6)
C5 0.0455(7) 0.0431(7) 0.0466(8) -0.0040(6) 0.0009(6) 0.0013(6)
C6 0.0599(9) 0.0482(8) 0.0489(8) 0.0046(6) -0.0062(6) 0.0046(7)
C7 0.0617(9) 0.0538(9) 0.0413(8) -0.0009(6) -0.0078(6) 0.0002(7)
C8 0.0619(9) 0.0452(8) 0.0496(8) 0.0005(6) -0.0019(7) 0.0001(7)
C9 0.0938(13) 0.0489(9) 0.0759(12) -0.0126(8) 0.0009(10) -0.0005(9)
C10 0.0472(7) 0.0488(8) 0.0429(7) -0.0018(6) -0.0008(6) 0.0001(6)
C11 0.0612(9) 0.0561(9) 0.0373(7) -0.0014(6) -0.0015(6) 0.0043(7)
C12 0.058(3) 0.062(2) 0.064(3) -0.020(2) 0.018(2) 0.004(2)
C13 0.058(2) 0.093(4) 0.120(5) -0.028(3) 0.010(3) 0.007(2)
C12' 0.093(9) 0.128(12) 0.086(7) -0.004(6) 0.024(5) 0.030(8)
C13' 0.090(5) 0.094(6) 0.102(6) -0.006(4) -0.005(4) 0.032(4)
C14 0.1112(16) 0.0810(13) 0.0616(11) 0.0074(9) -0.0292(11) 0.0177(12)
N1 0.0601(8) 0.0617(8) 0.0417(7) -0.0003(6) -0.0053(5) 0.0050(6)
O1 0.0870(8) 0.0465(6) 0.0497(6) -0.0088(4) -0.0072(5) 0.0007(5)
O2 0.0663(8) 0.0740(9) 0.1058(11) -0.0256(8) 0.0197(7) -0.0119(6)
O3 0.0562(6) 0.0439(6) 0.0554(6) -0.0068(4) 0.0024(4) 0.0049(4)
O4 0.0577(7) 0.0701(7) 0.0589(7) -0.0100(5) 0.0129(5) 0.0050(5)
O5 0.0854(9) 0.0654(7) 0.0581(7) -0.0169(6) -0.0112(6) 0.0063(6)
O6 0.0854(8) 0.0762(8) 0.0425(6) 0.0035(5) -0.0082(5) 0.0153(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.422(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.3627(17) . ?
C2 C7 1.384(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(2) . ?
C4 C10 1.483(2) . ?
C5 C6 1.374(2) . ?
C5 O3 1.4078(16) . ?
C6 C7 1.382(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O2 1.183(2) . ?
C8 O3 1.3613(19) . ?
C8 C9 1.486(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.2747(19) . ?
C10 C11 1.514(2) . ?
C11 O5 1.1967(19) . ?
C11 O4 1.3217(19) . ?
C12 O4 1.471(4) . ?
C12 C13 1.487(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12' O4 1.461(7) . ?
C12' C13' 1.483(14) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C14 O6 1.419(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 O6 1.4024(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 124.57(13) . . ?
O1 C2 C3 115.54(13) . . ?
C7 C2 C3 119.88(13) . . ?
C4 C3 C2 120.82(13) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.12(13) . . ?
C3 C4 C10 120.42(13) . . ?
C5 C4 C10 121.39(12) . . ?
C6 C5 C4 121.30(13) . . ?
C6 C5 O3 118.69(13) . . ?
C4 C5 O3 119.94(12) . . ?
C5 C6 C7 120.20(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 119.67(13) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
O2 C8 O3 122.47(14) . . ?
O2 C8 C9 126.49(16) . . ?
O3 C8 C9 111.04(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C4 118.62(13) . . ?
N1 C10 C11 122.35(13) . . ?
C4 C10 C11 118.92(12) . . ?
O5 C11 O4 126.33(15) . . ?
O5 C11 C10 125.23(15) . . ?
O4 C11 C10 108.43(12) . . ?
O4 C12 C13 105.4(5) . . ?
O4 C12 H12A 110.7 . . ?
C13 C12 H12A 110.7 . . ?
O4 C12 H12B 110.7 . . ?
C13 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
O4 C12' C13' 105.7(8) . . ?
O4 C12' H12C 110.6 . . ?
C13' C12' H12C 110.6 . . ?
O4 C12' H12D 110.6 . . ?
C13' C12' H12D 110.6 . . ?
H12C C12' H12D 108.7 . . ?
C12' C13' H13D 109.5 . . ?
C12' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 O6 111.10(12) . . ?
C2 O1 C1 117.88(12) . . ?
C8 O3 C5 117.07(11) . . ?
C11 O4 C12' 123.1(7) . . ?
C11 O4 C12 114.3(4) . . ?
C12' O4 C12 11.9(11) . . ?
N1 O6 C14 110.14(13) . . ?

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
O1 C2 C3 C4 178.19(13) . . . . ?
C7 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C10 -175.67(13) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C10 C4 C5 C6 175.89(13) . . . . ?
C3 C4 C5 O3 -177.71(12) . . . . ?
C10 C4 C5 O3 -0.8(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
O3 C5 C6 C7 176.57(13) . . . . ?
C5 C6 C7 C2 1.1(2) . . . . ?
O1 C2 C7 C6 -179.25(14) . . . . ?
C3 C2 C7 C6 -0.8(2) . . . . ?
C3 C4 C10 N1 -27.8(2) . . . . ?
C5 C4 C10 N1 155.38(14) . . . . ?
C3 C4 C10 C11 148.34(14) . . . . ?
C5 C4 C10 C11 -28.5(2) . . . . ?
N1 C10 C11 O5 -67.2(2) . . . . ?
C4 C10 C11 O5 116.82(17) . . . . ?
N1 C10 C11 O4 113.68(16) . . . . ?
C4 C10 C11 O4 -62.30(17) . . . . ?
C4 C10 N1 O6 174.87(12) . . . . ?
C11 C10 N1 O6 -1.1(2) . . . . ?
C7 C2 O1 C1 -0.4(2) . . . . ?
C3 C2 O1 C1 -178.89(14) . . . . ?
O2 C8 O3 C5 0.6(2) . . . . ?
C9 C8 O3 C5 -179.19(13) . . . . ?
C6 C5 O3 C8 90.01(16) . . . . ?
C4 C5 O3 C8 -93.20(16) . . . . ?
O5 C11 O4 C12' 0.5(8) . . . . ?
C10 C11 O4 C12' 179.6(8) . . . . ?
O5 C11 O4 C12 -8.6(5) . . . . ?
C10 C11 O4 C12 170.5(4) . . . . ?
C13' C12' O4 C11 -134.5(8) . . . . ?
C13' C12' O4 C12 -90(4) . . . . ?
C13 C12 O4 C11 -175.4(4) . . . . ?
C13 C12 O4 C12' 45(4) . . . . ?
C10 N1 O6 C14 -178.01(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041