# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_No1

_audit_creation_method           SHELXTL
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 O4'
_chemical_formula_sum            'C28 H20 O4'
_chemical_formula_weight         420.44

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'
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   Cc
_symmetry_space_group_name_Hall  'C -2yc'

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

_cell_length_a                   23.832(2)
_cell_length_b                   11.4009(10)
_cell_length_c                   7.7827(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.137(2)
_cell_angle_gamma                90.00
_cell_volume                     2106.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2687
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      26.42

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.088
_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      200(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            7630
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_av_sigmaI/netI    0.0992
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         28.31
_reflns_number_total             3544
_reflns_number_gt                2153
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0729P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3544
_refine_ls_number_parameters     290
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1677
_refine_ls_wR_factor_gt          0.1256
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 0.43934(17) 1.0652(4) 0.2672(6) 0.0423(10) Uani 1 1 d . . .
O1 O 0.47699(14) 0.9947(3) 0.3176(5) 0.0623(10) Uani 1 1 d . . .
C2 C 0.45581(18) 1.1925(4) 0.2577(6) 0.0419(10) Uani 1 1 d . . .
C3 C 0.5007(2) 1.2223(4) 0.1650(6) 0.0515(12) Uani 1 1 d . . .
H3 H 0.5202 1.1632 0.1082 0.062 Uiso 1 1 calc R . .
C4 C 0.5170(2) 1.3380(5) 0.1555(8) 0.0715(17) Uani 1 1 d . . .
H4 H 0.5473 1.3588 0.0902 0.086 Uiso 1 1 calc R . .
C5 C 0.4895(2) 1.4230(4) 0.2401(8) 0.0670(16) Uani 1 1 d . . .
H5 H 0.5009 1.5025 0.2333 0.080 Uiso 1 1 calc R . .
C6 C 0.4453(2) 1.3937(4) 0.3350(7) 0.0586(14) Uani 1 1 d . . .
H6 H 0.4269 1.4527 0.3955 0.070 Uiso 1 1 calc R . .
C7 C 0.42797(19) 1.2791(4) 0.3415(6) 0.0484(11) Uani 1 1 d . . .
H7 H 0.3968 1.2592 0.4037 0.058 Uiso 1 1 calc R . .
C8 C 0.38205(17) 1.0269(4) 0.2143(5) 0.0357(9) Uani 1 1 d . . .
C9 C 0.36918(16) 0.9045(3) 0.2135(5) 0.0346(9) Uani 1 1 d . . .
O2 O 0.40793(13) 0.8237(2) 0.2673(4) 0.0487(8) Uani 1 1 d . . .
H2 H 0.4388 0.8570 0.2955 0.073 Uiso 1 1 calc R . .
C10 C 0.31607(16) 0.8654(3) 0.1546(5) 0.0334(9) Uani 1 1 d . . .
C11 C 0.27438(17) 0.9472(3) 0.1023(5) 0.0354(9) Uani 1 1 d . . .
C12 C 0.28607(18) 1.0664(3) 0.1001(6) 0.0406(10) Uani 1 1 d . . .
H12 H 0.2573 1.1211 0.0637 0.049 Uiso 1 1 calc R . .
C13 C 0.33957(17) 1.1044(4) 0.1510(5) 0.0381(10) Uani 1 1 d . . .
H13 H 0.3480 1.1856 0.1432 0.046 Uiso 1 1 calc R . .
C14 C 0.30148(17) 0.7361(3) 0.1376(5) 0.0351(9) Uani 1 1 d . . .
H14 H 0.3358 0.6903 0.1140 0.042 Uiso 1 1 calc R . .
C15 C 0.25695(17) 0.7238(3) -0.0123(5) 0.0357(9) Uani 1 1 d . . .
H15A H 0.2467 0.6402 -0.0299 0.043 Uiso 1 1 calc R . .
H15B H 0.2714 0.7538 -0.1192 0.043 Uiso 1 1 calc R . .
C16 C 0.20590(19) 0.7937(3) 0.0290(6) 0.0413(10) Uani 1 1 d . . .
O3 O 0.22058(11) 0.9155(2) 0.0512(4) 0.0450(8) Uani 1 1 d . . .
O4 O 0.18451(13) 0.7535(3) 0.1833(4) 0.0490(8) Uani 1 1 d . . .
C17 C 0.2197(2) 0.6972(3) 0.3086(5) 0.0395(10) Uani 1 1 d . . .
C18 C 0.2777(2) 0.6888(3) 0.2953(6) 0.0407(10) Uani 1 1 d . . .
C19 C 0.3103(2) 0.6331(4) 0.4295(5) 0.0455(11) Uani 1 1 d . . .
H19 H 0.3499 0.6266 0.4245 0.055 Uiso 1 1 calc R . .
C20 C 0.2860(3) 0.5875(4) 0.5683(6) 0.0545(14) Uani 1 1 d . . .
H20 H 0.3089 0.5515 0.6598 0.065 Uiso 1 1 calc R . .
C21 C 0.2283(3) 0.5939(4) 0.5752(6) 0.0588(14) Uani 1 1 d . . .
H21 H 0.2113 0.5602 0.6694 0.071 Uiso 1 1 calc R . .
C22 C 0.1957(2) 0.6493(4) 0.4450(6) 0.0501(11) Uani 1 1 d . . .
H22 H 0.1561 0.6543 0.4500 0.060 Uiso 1 1 calc R . .
C23 C 0.15727(18) 0.7889(4) -0.1105(6) 0.0405(10) Uani 1 1 d . . .
C24 C 0.14758(19) 0.8781(4) -0.2307(6) 0.0474(11) Uani 1 1 d . . .
H24 H 0.1705 0.9465 -0.2241 0.057 Uiso 1 1 calc R . .
C25 C 0.1044(2) 0.8667(5) -0.3600(7) 0.0634(14) Uani 1 1 d . . .
H25 H 0.0974 0.9282 -0.4415 0.076 Uiso 1 1 calc R . .
C26 C 0.0715(2) 0.7687(5) -0.3730(8) 0.0662(15) Uani 1 1 d . . .
H26 H 0.0419 0.7624 -0.4626 0.079 Uiso 1 1 calc R . .
C27 C 0.0814(2) 0.6796(5) -0.2565(8) 0.0650(15) Uani 1 1 d . . .
H27 H 0.0589 0.6106 -0.2666 0.078 Uiso 1 1 calc R . .
C28 C 0.1237(2) 0.6893(4) -0.1246(7) 0.0566(13) Uani 1 1 d . . .
H28 H 0.1300 0.6276 -0.0431 0.068 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
C1 O1 1.242(5) . ?
C1 C8 1.458(6) . ?
C1 C2 1.507(6) . ?
C2 C7 1.385(6) . ?
C2 C3 1.385(7) . ?
C3 C4 1.379(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.400(6) . ?
C8 C9 1.428(5) . ?
C9 O2 1.345(4) . ?
C9 C10 1.381(5) . ?
O2 H2 0.8400 . ?
C10 C11 1.396(5) . ?
C10 C14 1.518(6) . ?
C11 O3 1.357(5) . ?
C11 C12 1.389(5) . ?
C12 C13 1.371(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C18 1.497(6) . ?
C14 C15 1.512(6) . ?
C14 H14 1.0000 . ?
C15 C16 1.513(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O4 1.422(5) . ?
C16 O3 1.438(5) . ?
C16 C23 1.517(7) . ?
O4 C17 1.385(5) . ?
C17 C22 1.364(6) . ?
C17 C18 1.399(6) . ?
C18 C19 1.398(6) . ?
C19 C20 1.373(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.387(6) . ?
C23 C24 1.388(6) . ?
C24 C25 1.380(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.362(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.369(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(7) . ?
C27 H27 0.9500 . ?
C28 H28 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
O1 C1 C8 121.8(4) . . ?
O1 C1 C2 117.1(4) . . ?
C8 C1 C2 121.1(3) . . ?
C7 C2 C3 119.7(4) . . ?
C7 C2 C1 121.7(4) . . ?
C3 C2 C1 118.6(4) . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 120.2(5) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C13 C8 C9 117.8(4) . . ?
C13 C8 C1 122.6(4) . . ?
C9 C8 C1 119.3(3) . . ?
O2 C9 C10 117.7(3) . . ?
O2 C9 C8 121.8(4) . . ?
C10 C9 C8 120.5(3) . . ?
C9 O2 H2 109.5 . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 C14 122.6(3) . . ?
C11 C10 C14 118.1(3) . . ?
O3 C11 C12 116.3(3) . . ?
O3 C11 C10 122.5(3) . . ?
C12 C11 C10 121.3(3) . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 121.8(4) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
C18 C14 C15 107.9(3) . . ?
C18 C14 C10 112.2(3) . . ?
C15 C14 C10 107.3(3) . . ?
C18 C14 H14 109.8 . . ?
C15 C14 H14 109.8 . . ?
C10 C14 H14 109.8 . . ?
C14 C15 C16 108.0(3) . . ?
C14 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
C14 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
O4 C16 O3 108.1(3) . . ?
O4 C16 C15 111.4(3) . . ?
O3 C16 C15 110.1(3) . . ?
O4 C16 C23 106.5(3) . . ?
O3 C16 C23 106.5(3) . . ?
C15 C16 C23 114.0(3) . . ?
C11 O3 C16 120.3(3) . . ?
C17 O4 C16 120.3(3) . . ?
C22 C17 O4 117.7(4) . . ?
C22 C17 C18 121.1(4) . . ?
O4 C17 C18 121.2(4) . . ?
C19 C18 C17 117.6(4) . . ?
C19 C18 C14 123.3(4) . . ?
C17 C18 C14 119.1(4) . . ?
C20 C19 C18 120.9(5) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.1(5) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.6(5) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C17 C22 C21 120.6(5) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C28 C23 C24 119.1(4) . . ?
C28 C23 C16 119.0(4) . . ?
C24 C23 C16 121.7(4) . . ?
C25 C24 C23 119.4(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 121.2(5) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C27 119.8(5) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 120.3(5) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.2(5) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?

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 C1 C2 C7 -125.2(5) . . . . ?
C8 C1 C2 C7 56.6(6) . . . . ?
O1 C1 C2 C3 53.6(6) . . . . ?
C8 C1 C2 C3 -124.6(5) . . . . ?
C7 C2 C3 C4 -0.6(7) . . . . ?
C1 C2 C3 C4 -179.4(4) . . . . ?
C2 C3 C4 C5 1.2(8) . . . . ?
C3 C4 C5 C6 -0.1(9) . . . . ?
C4 C5 C6 C7 -1.5(8) . . . . ?
C5 C6 C7 C2 2.0(7) . . . . ?
C3 C2 C7 C6 -1.0(7) . . . . ?
C1 C2 C7 C6 177.8(4) . . . . ?
O1 C1 C8 C13 -177.5(4) . . . . ?
C2 C1 C8 C13 0.6(7) . . . . ?
O1 C1 C8 C9 -2.6(7) . . . . ?
C2 C1 C8 C9 175.5(4) . . . . ?
C13 C8 C9 O2 178.1(4) . . . . ?
C1 C8 C9 O2 2.9(6) . . . . ?
C13 C8 C9 C10 -1.1(6) . . . . ?
C1 C8 C9 C10 -176.3(4) . . . . ?
O2 C9 C10 C11 178.3(4) . . . . ?
C8 C9 C10 C11 -2.5(6) . . . . ?
O2 C9 C10 C14 -4.2(6) . . . . ?
C8 C9 C10 C14 175.0(4) . . . . ?
C9 C10 C11 O3 -176.6(4) . . . . ?
C14 C10 C11 O3 5.7(6) . . . . ?
C9 C10 C11 C12 3.3(6) . . . . ?
C14 C10 C11 C12 -174.4(4) . . . . ?
O3 C11 C12 C13 179.7(4) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C8 -3.6(6) . . . . ?
C9 C8 C13 C12 4.2(6) . . . . ?
C1 C8 C13 C12 179.2(4) . . . . ?
C9 C10 C14 C18 93.2(5) . . . . ?
C11 C10 C14 C18 -89.2(5) . . . . ?
C9 C10 C14 C15 -148.4(4) . . . . ?
C11 C10 C14 C15 29.1(5) . . . . ?
C18 C14 C15 C16 60.1(4) . . . . ?
C10 C14 C15 C16 -61.0(4) . . . . ?
C14 C15 C16 O4 -59.1(4) . . . . ?
C14 C15 C16 O3 60.9(4) . . . . ?
C14 C15 C16 C23 -179.6(3) . . . . ?
C12 C11 O3 C16 172.4(4) . . . . ?
C10 C11 O3 C16 -7.7(6) . . . . ?
O4 C16 O3 C11 95.7(4) . . . . ?
C15 C16 O3 C11 -26.2(5) . . . . ?
C23 C16 O3 C11 -150.1(4) . . . . ?
O3 C16 O4 C17 -95.7(4) . . . . ?
C15 C16 O4 C17 25.4(5) . . . . ?
C23 C16 O4 C17 150.3(3) . . . . ?
C16 O4 C17 C22 -173.0(4) . . . . ?
C16 O4 C17 C18 6.5(5) . . . . ?
C22 C17 C18 C19 -2.0(6) . . . . ?
O4 C17 C18 C19 178.4(3) . . . . ?
C22 C17 C18 C14 176.1(4) . . . . ?
O4 C17 C18 C14 -3.4(5) . . . . ?
C15 C14 C18 C19 147.5(4) . . . . ?
C10 C14 C18 C19 -94.5(4) . . . . ?
C15 C14 C18 C17 -30.5(5) . . . . ?
C10 C14 C18 C17 87.4(4) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C14 C18 C19 C20 -177.6(4) . . . . ?
C18 C19 C20 C21 1.5(6) . . . . ?
C19 C20 C21 C22 -2.0(6) . . . . ?
O4 C17 C22 C21 -178.9(4) . . . . ?
C18 C17 C22 C21 1.6(6) . . . . ?
C20 C21 C22 C17 0.5(6) . . . . ?
O4 C16 C23 C28 -46.0(5) . . . . ?
O3 C16 C23 C28 -161.2(4) . . . . ?
C15 C16 C23 C28 77.2(5) . . . . ?
O4 C16 C23 C24 138.0(4) . . . . ?
O3 C16 C23 C24 22.8(6) . . . . ?
C15 C16 C23 C24 -98.7(5) . . . . ?
C28 C23 C24 C25 0.9(7) . . . . ?
C16 C23 C24 C25 176.9(4) . . . . ?
C23 C24 C25 C26 -0.8(8) . . . . ?
C24 C25 C26 C27 -0.2(8) . . . . ?
C25 C26 C27 C28 1.1(9) . . . . ?
C26 C27 C28 C23 -1.0(8) . . . . ?
C24 C23 C28 C27 0.0(7) . . . . ?
C16 C23 C28 C27 -176.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 981010'
#######################################################################
#
#                 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_10a

_audit_creation_method           SHELXTL
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 O5'
_chemical_formula_sum            'C23 H18 O5'
_chemical_formula_weight         374.37

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'
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)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   16.2287(9)
_cell_length_b                   6.0601(4)
_cell_length_c                   18.4712(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6080(10)
_cell_angle_gamma                90.00
_cell_volume                     1815.88(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3343
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      27.63

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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            12824
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         28.31
_reflns_number_total             4498
_reflns_number_gt                2308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0623P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4498
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
C1 C 0.98703(14) 0.6646(4) 0.07647(12) 0.0391(6) Uani 1 1 d . . .
O1 O 1.05714(10) 0.7855(3) 0.07581(9) 0.0507(5) Uani 1 1 d . . .
H1 H 1.0961 0.7124 0.0947 0.076 Uiso 1 1 calc R . .
C2 C 0.98398(14) 0.4550(4) 0.10930(12) 0.0366(5) Uani 1 1 d . . .
C3 C 0.91051(14) 0.3358(4) 0.10389(12) 0.0383(5) Uani 1 1 d . . .
H3 H 0.9087 0.1922 0.1244 0.046 Uiso 1 1 calc R . .
C4 C 0.84031(14) 0.4188(4) 0.06974(12) 0.0360(5) Uani 1 1 d . . .
C5 C 0.84439(14) 0.6337(4) 0.04247(12) 0.0377(5) Uani 1 1 d . . .
C6 C 0.91684(14) 0.7544(4) 0.04430(12) 0.0391(6) Uani 1 1 d . . .
H6 H 0.9183 0.8978 0.0236 0.047 Uiso 1 1 calc R . .
C7 C 1.05734(15) 0.3677(4) 0.14664(12) 0.0423(6) Uani 1 1 d . . .
O2 O 1.12553(11) 0.4546(3) 0.14614(9) 0.0541(5) Uani 1 1 d . . .
O3 O 1.04326(10) 0.1829(3) 0.18353(9) 0.0532(5) Uani 1 1 d . . .
C8 C 1.11225(17) 0.0776(5) 0.22043(16) 0.0653(8) Uani 1 1 d . . .
H8A H 1.1503 0.0204 0.1847 0.098 Uiso 1 1 calc R . .
H8B H 1.0923 -0.0445 0.2500 0.098 Uiso 1 1 calc R . .
H8C H 1.1410 0.1852 0.2516 0.098 Uiso 1 1 calc R . .
C9 C 0.76106(14) 0.2885(4) 0.06066(12) 0.0391(6) Uani 1 1 d . . .
H9 H 0.7737 0.1290 0.0525 0.047 Uiso 1 1 calc R . .
C10 C 0.70803(14) 0.3141(4) 0.12598(12) 0.0387(5) Uani 1 1 d . . .
C11 C 0.70403(14) 0.1602(4) 0.18131(13) 0.0450(6) Uani 1 1 d . . .
H11 H 0.7359 0.0290 0.1791 0.054 Uiso 1 1 calc R . .
C12 C 0.65418(15) 0.1955(5) 0.23978(13) 0.0505(7) Uani 1 1 d . . .
H12 H 0.6522 0.0896 0.2776 0.061 Uiso 1 1 calc R . .
C13 C 0.60735(15) 0.3849(4) 0.24298(13) 0.0487(6) Uani 1 1 d . . .
H13 H 0.5731 0.4089 0.2831 0.058 Uiso 1 1 calc R . .
C14 C 0.60996(15) 0.5401(4) 0.18826(13) 0.0464(6) Uani 1 1 d . . .
H14 H 0.5778 0.6708 0.1906 0.056 Uiso 1 1 calc R . .
C15 C 0.65994(14) 0.5027(4) 0.13009(12) 0.0395(6) Uani 1 1 d . . .
C16 C 0.71192(14) 0.3816(4) -0.00395(12) 0.0408(6) Uani 1 1 d . . .
H16A H 0.7426 0.3603 -0.0490 0.049 Uiso 1 1 calc R . .
H16B H 0.6582 0.3051 -0.0093 0.049 Uiso 1 1 calc R . .
C17 C 0.69875(14) 0.6248(4) 0.00978(12) 0.0384(6) Uani 1 1 d . . .
O4 O 0.77709(10) 0.7377(2) 0.01213(8) 0.0434(4) Uani 1 1 d . . .
O5 O 0.65995(10) 0.6645(3) 0.07684(8) 0.0462(4) Uani 1 1 d . . .
C18 C 0.64825(14) 0.7395(4) -0.04877(12) 0.0388(6) Uani 1 1 d . . .
C19 C 0.56499(15) 0.7771(4) -0.04297(14) 0.0514(7) Uani 1 1 d . . .
H19 H 0.5383 0.7339 -0.0001 0.062 Uiso 1 1 calc R . .
C20 C 0.51962(16) 0.8766(5) -0.09846(15) 0.0570(7) Uani 1 1 d . . .
H20 H 0.4623 0.9020 -0.0936 0.068 Uiso 1 1 calc R . .
C21 C 0.55795(17) 0.9384(5) -0.16065(15) 0.0553(7) Uani 1 1 d . . .
H21 H 0.5272 1.0074 -0.1989 0.066 Uiso 1 1 calc R . .
C22 C 0.64061(17) 0.9005(5) -0.16750(14) 0.0575(7) Uani 1 1 d . . .
H22 H 0.6670 0.9429 -0.2106 0.069 Uiso 1 1 calc R . .
C23 C 0.68588(16) 0.8007(4) -0.11197(13) 0.0503(7) Uani 1 1 d . . .
H23 H 0.7431 0.7742 -0.1173 0.060 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
C1 O1 1.354(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.409(3) . ?
O1 H1 0.8400 . ?
C2 C3 1.395(3) . ?
C2 C7 1.458(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 C9 1.515(3) . ?
C5 O4 1.368(3) . ?
C5 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C7 O2 1.226(3) . ?
C7 O3 1.334(3) . ?
O3 C8 1.443(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.510(3) . ?
C9 C16 1.525(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.387(3) . ?
C10 C15 1.387(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 O5 1.389(3) . ?
C16 C17 1.511(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O5 1.426(3) . ?
C17 O4 1.444(3) . ?
C17 C18 1.508(3) . ?
C18 C19 1.377(3) . ?
C18 C23 1.383(3) . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.370(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
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
O1 C1 C6 117.8(2) . . ?
O1 C1 C2 122.1(2) . . ?
C6 C1 C2 120.1(2) . . ?
C1 O1 H1 109.5 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 C7 122.1(2) . . ?
C1 C2 C7 119.5(2) . . ?
C4 C3 C2 122.4(2) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 117.2(2) . . ?
C3 C4 C9 123.2(2) . . ?
C5 C4 C9 119.6(2) . . ?
O4 C5 C6 115.7(2) . . ?
O4 C5 C4 122.1(2) . . ?
C6 C5 C4 122.1(2) . . ?
C1 C6 C5 119.4(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O2 C7 O3 122.2(2) . . ?
O2 C7 C2 124.5(2) . . ?
O3 C7 C2 113.4(2) . . ?
C7 O3 C8 118.1(2) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C4 111.05(18) . . ?
C10 C9 C16 106.85(18) . . ?
C4 C9 C16 108.50(19) . . ?
C10 C9 H9 110.1 . . ?
C4 C9 H9 110.1 . . ?
C16 C9 H9 110.1 . . ?
C11 C10 C15 118.4(2) . . ?
C11 C10 C9 124.0(2) . . ?
C15 C10 C9 117.6(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 119.2(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 O5 116.5(2) . . ?
C10 C15 O5 122.1(2) . . ?
C17 C16 C9 107.64(18) . . ?
C17 C16 H16A 110.2 . . ?
C9 C16 H16A 110.2 . . ?
C17 C16 H16B 110.2 . . ?
C9 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
O5 C17 O4 107.68(17) . . ?
O5 C17 C18 107.51(18) . . ?
O4 C17 C18 105.26(18) . . ?
O5 C17 C16 112.24(18) . . ?
O4 C17 C16 109.80(18) . . ?
C18 C17 C16 113.94(19) . . ?
C5 O4 C17 119.09(17) . . ?
C15 O5 C17 120.32(17) . . ?
C19 C18 C23 118.6(2) . . ?
C19 C18 C17 122.3(2) . . ?
C23 C18 C17 119.0(2) . . ?
C18 C19 C20 121.1(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.3(2) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?

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 C1 C2 C3 -176.32(19) . . . . ?
C6 C1 C2 C3 4.5(3) . . . . ?
O1 C1 C2 C7 2.7(3) . . . . ?
C6 C1 C2 C7 -176.53(19) . . . . ?
C1 C2 C3 C4 -2.2(3) . . . . ?
C7 C2 C3 C4 178.8(2) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C2 C3 C4 C9 177.44(19) . . . . ?
C3 C4 C5 O4 -175.44(18) . . . . ?
C9 C4 C5 O4 4.8(3) . . . . ?
C3 C4 C5 C6 4.7(3) . . . . ?
C9 C4 C5 C6 -175.01(19) . . . . ?
O1 C1 C6 C5 178.58(19) . . . . ?
C2 C1 C6 C5 -2.2(3) . . . . ?
O4 C5 C6 C1 177.61(19) . . . . ?
C4 C5 C6 C1 -2.6(3) . . . . ?
C3 C2 C7 O2 171.6(2) . . . . ?
C1 C2 C7 O2 -7.3(3) . . . . ?
C3 C2 C7 O3 -9.7(3) . . . . ?
C1 C2 C7 O3 171.38(19) . . . . ?
O2 C7 O3 C8 -3.5(3) . . . . ?
C2 C7 O3 C8 177.8(2) . . . . ?
C3 C4 C9 C10 86.9(3) . . . . ?
C5 C4 C9 C10 -93.4(2) . . . . ?
C3 C4 C9 C16 -156.0(2) . . . . ?
C5 C4 C9 C16 23.7(3) . . . . ?
C4 C9 C10 C11 -99.3(3) . . . . ?
C16 C9 C10 C11 142.5(2) . . . . ?
C4 C9 C10 C15 81.3(3) . . . . ?
C16 C9 C10 C15 -36.8(3) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 179.7(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C10 -0.7(4) . . . . ?
C13 C14 C15 O5 180.0(2) . . . . ?
C11 C10 C15 C14 1.0(4) . . . . ?
C9 C10 C15 C14 -179.6(2) . . . . ?
C11 C10 C15 O5 -179.7(2) . . . . ?
C9 C10 C15 O5 -0.3(3) . . . . ?
C10 C9 C16 C17 63.4(2) . . . . ?
C4 C9 C16 C17 -56.4(2) . . . . ?
C9 C16 C17 O5 -55.6(2) . . . . ?
C9 C16 C17 O4 64.1(2) . . . . ?
C9 C16 C17 C18 -178.12(18) . . . . ?
C6 C5 O4 C17 -178.52(17) . . . . ?
C4 C5 O4 C17 1.6(3) . . . . ?
O5 C17 O4 C5 86.0(2) . . . . ?
C18 C17 O4 C5 -159.58(18) . . . . ?
C16 C17 O4 C5 -36.5(2) . . . . ?
C14 C15 O5 C17 -169.8(2) . . . . ?
C10 C15 O5 C17 10.9(3) . . . . ?
O4 C17 O5 C15 -102.5(2) . . . . ?
C18 C17 O5 C15 144.6(2) . . . . ?
C16 C17 O5 C15 18.5(3) . . . . ?
O5 C17 C18 C19 -27.5(3) . . . . ?
O4 C17 C18 C19 -142.1(2) . . . . ?
C16 C17 C18 C19 97.5(3) . . . . ?
O5 C17 C18 C23 155.4(2) . . . . ?
O4 C17 C18 C23 40.8(3) . . . . ?
C16 C17 C18 C23 -79.6(3) . . . . ?
C23 C18 C19 C20 -0.9(4) . . . . ?
C17 C18 C19 C20 -178.0(2) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C23 -0.2(4) . . . . ?
C19 C18 C23 C22 0.9(4) . . . . ?
C17 C18 C23 C22 178.1(2) . . . . ?
C21 C22 C23 C18 -0.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 991036'
