# 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_cu_dm11239_0m
#TrackingRef 'cu_dm11239_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H32 O4'
_chemical_formula_weight         420.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.96350(10)
_cell_length_b                   13.7471(3)
_cell_length_c                   28.1129(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2304.72(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      70.53

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.499
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5818
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17561
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         64.98
_reflns_number_total             3887
_reflns_number_gt                3864
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0759P)²+0.6632P] 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   0.0(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_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 0.7496(3) 0.29925(10) 0.68760(5) 0.0349(3) Uani 1 1 d . . .
O2 O 0.9847(2) -0.03333(9) 0.80486(4) 0.0247(3) Uani 1 1 d . . .
H2 H 1.0533 -0.0852 0.8110 0.037 Uiso 1 1 calc R . .
O3 O 1.2081(3) -0.17523(10) 0.98041(5) 0.0320(3) Uani 1 1 d . . .
O4 O 1.3732(5) -0.0160(2) 1.11028(8) 0.0932(9) Uani 1 1 d . . .
C1 C 0.7027(3) 0.27373(13) 0.81331(7) 0.0240(4) Uani 1 1 d . . .
H1 H 0.7301 0.3124 0.8407 0.029 Uiso 1 1 calc R . .
C2 C 0.7437(3) 0.31309(13) 0.77075(7) 0.0280(4) Uani 1 1 d . . .
H2A H 0.8027 0.3772 0.7694 0.034 Uiso 1 1 calc R . .
C3 C 0.7013(3) 0.26122(13) 0.72565(7) 0.0260(4) Uani 1 1 d . . .
C4 C 0.5919(3) 0.16017(13) 0.72755(7) 0.0249(4) Uani 1 1 d . . .
C5 C 0.6688(3) 0.11285(12) 0.77480(6) 0.0202(4) Uani 1 1 d . . .
H5 H 0.8362 0.1140 0.7728 0.024 Uiso 1 1 calc R . .
C6 C 0.6117(3) 0.00417(12) 0.78022(6) 0.0219(4) Uani 1 1 d . . .
H6A H 0.4508 -0.0031 0.7881 0.026 Uiso 1 1 calc R . .
H6B H 0.6397 -0.0298 0.7497 0.026 Uiso 1 1 calc R . .
C7 C 0.7547(3) -0.04222(12) 0.81958(6) 0.0216(4) Uani 1 1 d . . .
H7 H 0.7146 -0.1125 0.8230 0.026 Uiso 1 1 calc R . .
C8 C 0.7128(3) 0.01095(12) 0.86686(6) 0.0201(4) Uani 1 1 d . . .
C9 C 0.7586(3) 0.12123(12) 0.85960(6) 0.0191(4) Uani 1 1 d . . .
H9 H 0.9150 0.1238 0.8468 0.023 Uiso 1 1 calc R . .
C10 C 0.6155(3) 0.17156(13) 0.82072(6) 0.0213(4) Uani 1 1 d . . .
C11 C 0.7796(3) 0.16118(13) 0.91031(6) 0.0232(4) Uani 1 1 d . . .
H11A H 0.8700 0.2215 0.9113 0.028 Uiso 1 1 calc R . .
H11B H 0.6309 0.1734 0.9248 0.028 Uiso 1 1 calc R . .
C12 C 0.8999(3) 0.07668(13) 0.93420(6) 0.0225(4) Uani 1 1 d . . .
C13 C 1.0222(3) 0.07636(13) 0.97655(6) 0.0234(4) Uani 1 1 d . . .
C14 C 0.8728(3) -0.00810(13) 0.90798(6) 0.0216(4) Uani 1 1 d . . .
C15 C 0.9673(3) -0.09525(13) 0.92232(6) 0.0230(4) Uani 1 1 d . . .
H15 H 0.9450 -0.1532 0.9045 0.028 Uiso 1 1 calc R . .
C16 C 1.0965(3) -0.09547(14) 0.96374(6) 0.0252(4) Uani 1 1 d . . .
C17 C 1.1238(3) -0.01055(14) 0.99098(6) 0.0247(4) Uani 1 1 d . . .
C18 C 1.0414(4) 0.16752(14) 1.00615(7) 0.0306(4) Uani 1 1 d . . .
H18A H 1.0278 0.2247 0.9855 0.046 Uiso 1 1 calc R . .
H18B H 1.1874 0.1686 1.0222 0.046 Uiso 1 1 calc R . .
H18C H 0.9216 0.1685 1.0300 0.046 Uiso 1 1 calc R . .
C19 C 0.3659(3) 0.18020(15) 0.83474(7) 0.0286(4) Uani 1 1 d . . .
H19A H 0.3539 0.1902 0.8692 0.043 Uiso 1 1 calc R . .
H19B H 0.2870 0.1203 0.8259 0.043 Uiso 1 1 calc R . .
H19C H 0.2984 0.2355 0.8181 0.043 Uiso 1 1 calc R . .
C20 C 1.2665(3) -0.01208(15) 1.03429(6) 0.0283(4) Uani 1 1 d . . .
C21 C 1.1983(5) -0.0258(3) 1.08059(8) 0.0676(10) Uani 1 1 d . . .
H21 H 1.0490 -0.0401 1.0901 0.081 Uiso 1 1 calc R . .
C22 C 1.4912(4) 0.00561(19) 1.03717(8) 0.0439(5) Uani 1 1 d . . .
H22 H 1.5862 0.0191 1.0108 0.053 Uiso 1 1 calc R . .
C23 C 1.5589(3) 0.00115(17) 1.08319(7) 0.0353(5) Uani 1 1 d . . .
H23 H 1.7080 0.0086 1.0945 0.042 Uiso 1 1 calc R . .
C24 C 1.1901(4) -0.26306(15) 0.95352(8) 0.0378(5) Uani 1 1 d . . .
H24A H 1.0334 -0.2845 0.9530 0.057 Uiso 1 1 calc R . .
H24B H 1.2831 -0.3136 0.9682 0.057 Uiso 1 1 calc R . .
H24C H 1.2416 -0.2514 0.9209 0.057 Uiso 1 1 calc R . .
C28 C 0.3366(3) 0.17450(16) 0.72203(8) 0.0346(5) Uani 1 1 d . . .
H28A H 0.2866 0.2269 0.7432 0.052 Uiso 1 1 calc R . .
H28B H 0.2591 0.1140 0.7304 0.052 Uiso 1 1 calc R . .
H28C H 0.3021 0.1917 0.6890 0.052 Uiso 1 1 calc R . .
C29 C 0.6779(4) 0.10139(15) 0.68488(7) 0.0336(5) Uani 1 1 d . . .
H29A H 0.6726 0.1419 0.6562 0.050 Uiso 1 1 calc R . .
H29B H 0.5831 0.0439 0.6804 0.050 Uiso 1 1 calc R . .
H29C H 0.8328 0.0809 0.6908 0.050 Uiso 1 1 calc R . .
C30 C 0.4791(3) -0.01767(13) 0.88557(6) 0.0249(4) Uani 1 1 d . . .
H30A H 0.4801 -0.0862 0.8951 0.037 Uiso 1 1 calc R . .
H30B H 0.3675 -0.0080 0.8604 0.037 Uiso 1 1 calc R . .
H30C H 0.4409 0.0230 0.9130 0.037 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
O1 C3 1.225(2) . ?
O2 C7 1.438(2) . ?
O2 H2 0.8400 . ?
O3 C16 1.366(2) . ?
O3 C24 1.429(2) . ?
O4 C21 1.343(3) . ?
O4 C23 1.364(3) . ?
C1 C2 1.336(3) . ?
C1 C10 1.512(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.476(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.536(3) . ?
C4 C29 1.535(3) . ?
C4 C28 1.543(3) . ?
C4 C5 1.548(2) . ?
C5 C6 1.540(2) . ?
C5 C10 1.555(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.536(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.537(2) . ?
C7 H7 1.0000 . ?
C8 C14 1.521(2) . ?
C8 C30 1.541(2) . ?
C8 C9 1.554(2) . ?
C9 C11 1.533(2) . ?
C9 C10 1.549(2) . ?
C9 H9 1.0000 . ?
C10 C19 1.545(3) . ?
C11 C12 1.522(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.389(3) . ?
C12 C13 1.396(3) . ?
C13 C17 1.400(3) . ?
C13 C18 1.509(2) . ?
C14 C15 1.384(3) . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.406(3) . ?
C17 C20 1.486(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C22 1.364(3) . ?
C20 C21 1.377(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.357(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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 O2 H2 109.5 . . ?
C16 O3 C24 117.42(15) . . ?
C21 O4 C23 107.50(19) . . ?
C2 C1 C10 124.24(16) . . ?
C2 C1 H1 117.9 . . ?
C10 C1 H1 117.9 . . ?
C1 C2 C3 122.84(17) . . ?
C1 C2 H2A 118.6 . . ?
C3 C2 H2A 118.6 . . ?
O1 C3 C2 120.23(17) . . ?
O1 C3 C4 121.09(17) . . ?
C2 C3 C4 118.67(16) . . ?
C29 C4 C3 107.90(16) . . ?
C29 C4 C28 108.55(17) . . ?
C3 C4 C28 107.47(16) . . ?
C29 C4 C5 110.51(15) . . ?
C3 C4 C5 106.51(14) . . ?
C28 C4 C5 115.60(16) . . ?
C6 C5 C4 115.28(14) . . ?
C6 C5 C10 112.09(14) . . ?
C4 C5 C10 115.69(14) . . ?
C6 C5 H5 104.0 . . ?
C4 C5 H5 104.0 . . ?
C10 C5 H5 104.0 . . ?
C7 C6 C5 110.58(14) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O2 C7 C6 106.68(13) . . ?
O2 C7 C8 111.32(14) . . ?
C6 C7 C8 109.58(14) . . ?
O2 C7 H7 109.7 . . ?
C6 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C14 C8 C7 118.23(14) . . ?
C14 C8 C30 105.31(13) . . ?
C7 C8 C30 108.71(14) . . ?
C14 C8 C9 99.07(13) . . ?
C7 C8 C9 108.76(13) . . ?
C30 C8 C9 116.93(14) . . ?
C11 C9 C10 122.75(14) . . ?
C11 C9 C8 103.99(13) . . ?
C10 C9 C8 115.58(14) . . ?
C11 C9 H9 104.2 . . ?
C10 C9 H9 104.2 . . ?
C8 C9 H9 104.2 . . ?
C1 C10 C19 107.16(15) . . ?
C1 C10 C9 108.83(14) . . ?
C19 C10 C9 112.63(15) . . ?
C1 C10 C5 107.30(14) . . ?
C19 C10 C5 116.65(15) . . ?
C9 C10 C5 103.97(14) . . ?
C12 C11 C9 100.11(14) . . ?
C12 C11 H11A 111.7 . . ?
C9 C11 H11A 111.7 . . ?
C12 C11 H11B 111.8 . . ?
C9 C11 H11B 111.7 . . ?
H11A C11 H11B 109.5 . . ?
C14 C12 C13 120.73(16) . . ?
C14 C12 C11 110.57(15) . . ?
C13 C12 C11 128.70(16) . . ?
C12 C13 C17 118.42(16) . . ?
C12 C13 C18 120.49(17) . . ?
C17 C13 C18 121.09(16) . . ?
C15 C14 C12 121.63(16) . . ?
C15 C14 C8 128.73(16) . . ?
C12 C14 C8 109.39(15) . . ?
C14 C15 C16 118.00(17) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
O3 C16 C15 123.84(17) . . ?
O3 C16 C17 115.05(16) . . ?
C15 C16 C17 121.10(17) . . ?
C13 C17 C16 120.05(16) . . ?
C13 C17 C20 119.84(17) . . ?
C16 C17 C20 120.08(17) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C21 104.99(19) . . ?
C22 C20 C17 127.50(19) . . ?
C21 C20 C17 127.4(2) . . ?
O4 C21 C20 110.1(2) . . ?
O4 C21 H21 124.9 . . ?
C20 C21 H21 124.9 . . ?
C23 C22 C20 109.9(2) . . ?
C23 C22 H22 125.0 . . ?
C20 C22 H22 125.0 . . ?
C22 C23 O4 107.4(2) . . ?
C22 C23 H23 126.3 . . ?
O4 C23 H23 126.3 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4 C28 H28A 109.5 . . ?
C4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C4 C29 H29A 109.5 . . ?
C4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C8 C30 H30A 109.5 . . ?
C8 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C8 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        64.98
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 875034'
#######################################################################
#
#                 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_cu_dm11242_0m
#TrackingRef 'cu_dm11242_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H36 O4'
_chemical_formula_weight         424.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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                   8.2016(5)
_cell_length_b                   10.1084(6)
_cell_length_c                   13.3847(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.338(3)
_cell_angle_gamma                90.00
_cell_volume                     1109.36(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5229
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      67.62

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9073
_exptl_absorpt_correction_T_max  0.9368
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6217
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0956
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         64.98
_reflns_number_total             3273
_reflns_number_gt                3122
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.1025P)²+0.8888P] 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   0.0(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3273
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1858
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.0689(5) 0.6604(4) 0.2417(3) 0.0392(8) Uani 1 1 d . . .
H1 H 0.0343 0.6885 0.1861 0.059 Uiso 1 1 calc R . .
O2 O 0.3525(4) 0.7153(3) 0.5628(2) 0.0255(6) Uani 1 1 d . . .
H2 H 0.3089 0.7391 0.6160 0.038 Uiso 1 1 calc R . .
O3 O 0.2272(3) 0.7090(3) 0.9611(2) 0.0262(6) Uani 1 1 d . . .
O4 O -0.2597(4) 0.6431(4) 1.0994(2) 0.0345(8) Uani 1 1 d . . .
C1 C -0.0301(5) 0.4555(5) 0.3867(3) 0.0271(9) Uani 1 1 d . . .
H1A H -0.1129 0.3931 0.4115 0.033 Uiso 1 1 calc R . .
H1B H -0.0696 0.5464 0.3993 0.033 Uiso 1 1 calc R . .
C2 C -0.0143(6) 0.4361(5) 0.2745(3) 0.0291(9) Uani 1 1 d . . .
H2A H -0.1199 0.4567 0.2407 0.035 Uiso 1 1 calc R . .
H2B H 0.0120 0.3424 0.2608 0.035 Uiso 1 1 calc R . .
C3 C 0.1184(6) 0.5244(5) 0.2320(3) 0.0290(10) Uani 1 1 d . . .
H3 H 0.1296 0.5036 0.1594 0.035 Uiso 1 1 calc R . .
C4 C 0.2844(6) 0.5060(5) 0.2848(3) 0.0280(10) Uani 1 1 d . . .
C5 C 0.2627(5) 0.5248(4) 0.3993(3) 0.0210(8) Uani 1 1 d . . .
H5 H 0.2170 0.6161 0.4053 0.025 Uiso 1 1 calc R . .
C6 C 0.4215(5) 0.5291(4) 0.4625(3) 0.0230(8) Uani 1 1 d . . .
H6A H 0.4694 0.4392 0.4651 0.028 Uiso 1 1 calc R . .
H6B H 0.5003 0.5879 0.4294 0.028 Uiso 1 1 calc R . .
C7 C 0.3973(5) 0.5782(4) 0.5698(3) 0.0220(8) Uani 1 1 d . . .
H7 H 0.5024 0.5699 0.6087 0.026 Uiso 1 1 calc R . .
C8 C 0.2651(5) 0.4944(4) 0.6203(3) 0.0199(8) Uani 1 1 d . . .
C9 C 0.1113(5) 0.4906(4) 0.5517(3) 0.0208(8) Uani 1 1 d . . .
H9 H 0.0856 0.5861 0.5398 0.025 Uiso 1 1 calc R . .
C10 C 0.1302(5) 0.4340(4) 0.4456(3) 0.0206(8) Uani 1 1 d . . .
C11 C -0.0261(5) 0.4436(5) 0.6193(3) 0.0244(9) Uani 1 1 d . . .
H11A H -0.1344 0.4740 0.5945 0.029 Uiso 1 1 calc R . .
H11B H -0.0269 0.3461 0.6265 0.029 Uiso 1 1 calc R . .
C12 C 0.0250(5) 0.5123(4) 0.7171(3) 0.0211(8) Uani 1 1 d . . .
C13 C -0.0702(5) 0.5395(4) 0.7996(3) 0.0227(8) Uani 1 1 d . . .
C14 C 0.1885(5) 0.5481(4) 0.7147(3) 0.0205(8) Uani 1 1 d . . .
C15 C 0.2623(5) 0.6133(4) 0.7961(3) 0.0227(8) Uani 1 1 d . . .
H15 H 0.3747 0.6360 0.7955 0.027 Uiso 1 1 calc R . .
C16 C 0.1683(5) 0.6442(4) 0.8777(3) 0.0217(8) Uani 1 1 d . . .
C17 C 0.0016(5) 0.6077(4) 0.8808(3) 0.0211(8) Uani 1 1 d . . .
C18 C -0.2454(5) 0.4963(5) 0.7988(3) 0.0288(9) Uani 1 1 d . . .
H18A H -0.2873 0.4922 0.7297 0.043 Uiso 1 1 calc R . .
H18B H -0.3098 0.5598 0.8366 0.043 Uiso 1 1 calc R . .
H18C H -0.2534 0.4086 0.8296 0.043 Uiso 1 1 calc R . .
C19 C 0.1737(6) 0.2853(4) 0.4479(3) 0.0284(9) Uani 1 1 d . . .
H19A H 0.1253 0.2439 0.5064 0.043 Uiso 1 1 calc R . .
H19B H 0.2925 0.2750 0.4518 0.043 Uiso 1 1 calc R . .
H19C H 0.1309 0.2427 0.3870 0.043 Uiso 1 1 calc R . .
C20 C -0.0953(5) 0.6472(4) 0.9688(3) 0.0224(8) Uani 1 1 d . . .
C21 C -0.1855(5) 0.5707(5) 1.0277(3) 0.0272(9) Uani 1 1 d . . .
H21 H -0.1963 0.4776 1.0204 0.033 Uiso 1 1 calc R . .
C22 C -0.1143(6) 0.7795(5) 1.0075(3) 0.0293(9) Uani 1 1 d . . .
H22 H -0.0655 0.8579 0.9829 0.035 Uiso 1 1 calc R . .
C23 C -0.2134(6) 0.7704(5) 1.0842(3) 0.0319(10) Uani 1 1 d . . .
H23 H -0.2476 0.8433 1.1233 0.038 Uiso 1 1 calc R . .
C24 C 0.3958(6) 0.7353(5) 0.9673(3) 0.0335(11) Uani 1 1 d . . .
H24A H 0.4565 0.6520 0.9627 0.050 Uiso 1 1 calc R . .
H24B H 0.4225 0.7784 1.0311 0.050 Uiso 1 1 calc R . .
H24C H 0.4258 0.7936 0.9122 0.050 Uiso 1 1 calc R . .
C28 C 0.3556(6) 0.3717(5) 0.2546(3) 0.0364(11) Uani 1 1 d . . .
H28A H 0.2784 0.3012 0.2705 0.055 Uiso 1 1 calc R . .
H28B H 0.4588 0.3567 0.2913 0.055 Uiso 1 1 calc R . .
H28C H 0.3752 0.3714 0.1826 0.055 Uiso 1 1 calc R . .
C29 C 0.3999(6) 0.6135(6) 0.2460(3) 0.0393(12) Uani 1 1 d . . .
H29A H 0.3866 0.6208 0.1732 0.059 Uiso 1 1 calc R . .
H29B H 0.5130 0.5896 0.2631 0.059 Uiso 1 1 calc R . .
H29C H 0.3737 0.6985 0.2769 0.059 Uiso 1 1 calc R . .
C30 C 0.3418(5) 0.3598(4) 0.6504(3) 0.0243(9) Uani 1 1 d . . .
H30A H 0.4186 0.3727 0.7067 0.037 Uiso 1 1 calc R . .
H30B H 0.3998 0.3230 0.5935 0.037 Uiso 1 1 calc R . .
H30C H 0.2556 0.2986 0.6699 0.037 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
O1 C3 1.439(6) . ?
O1 H1 0.8400 . ?
O2 C7 1.436(5) . ?
O2 H2 0.8400 . ?
O3 C16 1.373(5) . ?
O3 C24 1.409(5) . ?
O4 C23 1.358(7) . ?
O4 C21 1.362(6) . ?
C1 C2 1.523(6) . ?
C1 C10 1.533(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.528(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.531(7) . ?
C3 H3 1.0000 . ?
C4 C28 1.536(7) . ?
C4 C29 1.540(7) . ?
C4 C5 1.559(5) . ?
C5 C6 1.537(6) . ?
C5 C10 1.562(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.537(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.544(5) . ?
C7 H7 1.0000 . ?
C8 C14 1.525(5) . ?
C8 C9 1.543(6) . ?
C8 C30 1.548(6) . ?
C9 C11 1.537(5) . ?
C9 C10 1.541(5) . ?
C9 H9 1.0000 . ?
C10 C19 1.545(6) . ?
C11 C12 1.532(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.390(6) . ?
C12 C13 1.395(6) . ?
C13 C17 1.404(6) . ?
C13 C18 1.502(6) . ?
C14 C15 1.399(6) . ?
C15 C16 1.387(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.418(6) . ?
C17 C20 1.491(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.340(6) . ?
C20 C22 1.445(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.327(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.5 . . ?
C7 O2 H2 109.5 . . ?
C16 O3 C24 117.6(3) . . ?
C23 O4 C21 105.8(3) . . ?
C2 C1 C10 113.4(3) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 C3 111.7(4) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 C2 108.6(4) . . ?
O1 C3 C4 108.9(4) . . ?
C2 C3 C4 113.0(4) . . ?
O1 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
C3 C4 C28 109.0(4) . . ?
C3 C4 C29 107.8(4) . . ?
C28 C4 C29 107.1(4) . . ?
C3 C4 C5 108.6(3) . . ?
C28 C4 C5 114.8(4) . . ?
C29 C4 C5 109.3(4) . . ?
C6 C5 C4 115.5(3) . . ?
C6 C5 C10 112.7(3) . . ?
C4 C5 C10 114.5(3) . . ?
C6 C5 H5 104.1 . . ?
C4 C5 H5 104.1 . . ?
C10 C5 H5 104.1 . . ?
C7 C6 C5 113.4(3) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O2 C7 C6 106.8(3) . . ?
O2 C7 C8 112.2(3) . . ?
C6 C7 C8 109.8(3) . . ?
O2 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C14 C8 C9 98.9(3) . . ?
C14 C8 C7 118.3(3) . . ?
C9 C8 C7 109.0(3) . . ?
C14 C8 C30 105.7(3) . . ?
C9 C8 C30 117.0(3) . . ?
C7 C8 C30 108.1(3) . . ?
C11 C9 C10 121.2(3) . . ?
C11 C9 C8 104.9(3) . . ?
C10 C9 C8 117.3(3) . . ?
C11 C9 H9 103.7 . . ?
C10 C9 H9 103.7 . . ?
C8 C9 H9 103.7 . . ?
C1 C10 C9 108.5(3) . . ?
C1 C10 C19 110.1(3) . . ?
C9 C10 C19 111.8(3) . . ?
C1 C10 C5 108.0(3) . . ?
C9 C10 C5 103.5(3) . . ?
C19 C10 C5 114.6(3) . . ?
C12 C11 C9 100.0(3) . . ?
C12 C11 H11A 111.8 . . ?
C9 C11 H11A 111.8 . . ?
C12 C11 H11B 111.8 . . ?
C9 C11 H11B 111.8 . . ?
H11A C11 H11B 109.5 . . ?
C14 C12 C13 121.7(4) . . ?
C14 C12 C11 110.1(3) . . ?
C13 C12 C11 128.2(4) . . ?
C12 C13 C17 118.5(4) . . ?
C12 C13 C18 119.3(4) . . ?
C17 C13 C18 122.2(3) . . ?
C12 C14 C15 120.3(3) . . ?
C12 C14 C8 110.1(3) . . ?
C15 C14 C8 129.3(4) . . ?
C16 C15 C14 118.7(4) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
O3 C16 C15 123.8(4) . . ?
O3 C16 C17 114.9(3) . . ?
C15 C16 C17 121.2(4) . . ?
C13 C17 C16 119.5(3) . . ?
C13 C17 C20 121.4(4) . . ?
C16 C17 C20 119.0(4) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 104.9(4) . . ?
C21 C20 C17 128.5(4) . . ?
C22 C20 C17 126.5(4) . . ?
C20 C21 O4 111.5(4) . . ?
C20 C21 H21 124.2 . . ?
O4 C21 H21 124.2 . . ?
C23 C22 C20 106.6(4) . . ?
C23 C22 H22 126.7 . . ?
C20 C22 H22 126.7 . . ?
C22 C23 O4 111.1(4) . . ?
C22 C23 H23 124.4 . . ?
O4 C23 H23 124.4 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4 C28 H28A 109.5 . . ?
C4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C4 C29 H29A 109.5 . . ?
C4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C8 C30 H30A 109.5 . . ?
C8 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C8 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        64.98
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 875035'
