# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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_global


data_dm12579
#TrackingRef 'dm12579.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 O8'
_chemical_formula_weight         440.43

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)/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                   14.0632(14)
_cell_length_b                   7.2591(7)
_cell_length_c                   11.4968(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.2380(10)
_cell_angle_gamma                90.00
_cell_volume                     1093.95(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    5496
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      30.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10346
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         30.67
_reflns_number_total             3382
_reflns_number_gt                2945
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0656P)^2^+0.3300P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3382
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001

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 0.40571(7) 1.16170(14) 0.70447(9) 0.0386(2) Uani 1 1 d . . .
O2 O 0.37061(6) 1.03144(11) 0.51547(7) 0.02812(18) Uani 1 1 d . . .
O3 O -0.15609(5) 0.62160(10) 0.63690(7) 0.02269(16) Uani 1 1 d . . .
O4 O -0.01918(6) 0.45178(11) 0.74756(7) 0.02435(16) Uani 1 1 d . . .
C1 C 0.07922(6) 0.52547(12) 0.56733(8) 0.01617(16) Uani 1 1 d . . .
H1 H 0.1083 0.4460 0.6431 0.019 Uiso 1 1 calc R . .
C2 C -0.02810(6) 0.59662(12) 0.55398(8) 0.01601(17) Uani 1 1 d . . .
H2 H -0.0358 0.7312 0.5344 0.019 Uiso 1 1 calc R . .
C5 C 0.15643(6) 0.66468(12) 0.56090(8) 0.01686(17) Uani 1 1 d . . .
C6 C 0.12643(7) 0.81903(13) 0.48330(9) 0.01962(18) Uani 1 1 d . . .
H6 H 0.0559 0.8404 0.4386 0.024 Uiso 1 1 calc R . .
C7 C 0.19783(7) 0.94176(14) 0.47037(9) 0.02156(19) Uani 1 1 d . . .
H7 H 0.1767 1.0460 0.4173 0.026 Uiso 1 1 calc R . .
C8 C 0.30021(7) 0.90932(14) 0.53623(9) 0.02202(19) Uani 1 1 d . . .
C9 C 0.33327(7) 0.75750(15) 0.61304(9) 0.0243(2) Uani 1 1 d . . .
H9 H 0.4040 0.7367 0.6567 0.029 Uiso 1 1 calc R . .
C10 C 0.26084(7) 0.63551(14) 0.62525(9) 0.02126(19) Uani 1 1 d . . .
H10 H 0.2827 0.5310 0.6780 0.026 Uiso 1 1 calc R . .
C11 C 0.48016(10) 1.28721(18) 0.56311(13) 0.0372(3) Uani 1 1 d . . .
H11A H 0.4932 1.3996 0.6137 0.056 Uiso 1 1 calc R . .
H11B H 0.4440 1.3187 0.4752 0.056 Uiso 1 1 calc R . .
H11C H 0.5452 1.2279 0.5727 0.056 Uiso 1 1 calc R . .
C12 C 0.41631(7) 1.15803(15) 0.60551(10) 0.0248(2) Uani 1 1 d . . .
C13 C -0.06366(7) 0.54800(13) 0.65889(8) 0.01772(17) Uani 1 1 d . . .
C14 C -0.20546(9) 0.56977(18) 0.72249(12) 0.0337(3) Uani 1 1 d . . .
H14A H -0.2201 0.4374 0.7150 0.051 Uiso 1 1 calc R . .
H14B H -0.2694 0.6386 0.7024 0.051 Uiso 1 1 calc R . .
H14C H -0.1604 0.5982 0.8081 0.051 Uiso 1 1 calc R . .

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
O1 0.0433(5) 0.0436(5) 0.0360(5) -0.0115(4) 0.0228(4) -0.0222(4)
O2 0.0288(4) 0.0299(4) 0.0308(4) -0.0047(3) 0.0170(3) -0.0139(3)
O3 0.0228(3) 0.0229(3) 0.0270(3) 0.0034(3) 0.0145(3) 0.0012(3)
O4 0.0263(4) 0.0273(4) 0.0187(3) 0.0031(3) 0.0072(3) -0.0010(3)
C1 0.0162(3) 0.0150(4) 0.0166(4) 0.0013(3) 0.0050(3) -0.0012(3)
C2 0.0167(4) 0.0142(4) 0.0178(4) 0.0005(3) 0.0070(3) -0.0016(3)
C5 0.0163(4) 0.0165(4) 0.0172(4) -0.0008(3) 0.0054(3) -0.0027(3)
C6 0.0181(4) 0.0184(4) 0.0213(4) 0.0021(3) 0.0059(3) -0.0020(3)
C7 0.0239(4) 0.0180(4) 0.0240(4) 0.0018(3) 0.0102(3) -0.0029(3)
C8 0.0217(4) 0.0222(4) 0.0251(4) -0.0034(3) 0.0119(3) -0.0079(3)
C9 0.0163(4) 0.0276(5) 0.0279(5) 0.0000(4) 0.0067(3) -0.0031(3)
C10 0.0175(4) 0.0212(4) 0.0235(4) 0.0028(3) 0.0056(3) -0.0002(3)
C11 0.0406(6) 0.0349(6) 0.0419(6) -0.0034(5) 0.0218(5) -0.0200(5)
C12 0.0211(4) 0.0235(5) 0.0318(5) -0.0012(4) 0.0120(4) -0.0063(3)
C13 0.0194(4) 0.0156(4) 0.0190(4) -0.0025(3) 0.0079(3) -0.0036(3)
C14 0.0346(5) 0.0379(6) 0.0394(6) 0.0057(5) 0.0263(5) 0.0007(5)

_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 C12 1.2002(14) . ?
O2 C12 1.3590(13) . ?
O2 C8 1.4122(11) . ?
O3 C13 1.3420(11) . ?
O3 C14 1.4446(12) . ?
O4 C13 1.2068(12) . ?
C1 C5 1.5046(12) . ?
C1 C2 1.5494(12) . ?
C1 C2 1.5877(12) 3_566 ?
C1 H1 1.0000 . ?
C2 C13 1.5054(12) . ?
C2 C1 1.5878(12) 3_566 ?
C2 H2 1.0000 . ?
C5 C6 1.3987(12) . ?
C5 C10 1.4004(12) . ?
C6 C7 1.3900(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.3827(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.3831(15) . ?
C9 C10 1.3947(13) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.4968(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C12 O2 C8 117.57(8) . . ?
C13 O3 C14 116.09(8) . . ?
C5 C1 C2 117.76(7) . . ?
C5 C1 C2 115.90(7) . 3_566 ?
C2 C1 C2 89.09(6) . 3_566 ?
C5 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
C2 C1 H1 110.8 3_566 . ?
C13 C2 C1 115.90(7) . . ?
C13 C2 C1 113.38(7) . 3_566 ?
C1 C2 C1 90.91(6) . 3_566 ?
C13 C2 H2 111.7 . . ?
C1 C2 H2 111.7 . . ?
C1 C2 H2 111.7 3_566 . ?
C6 C5 C10 118.32(8) . . ?
C6 C5 C1 120.87(8) . . ?
C10 C5 C1 120.64(8) . . ?
C7 C6 C5 121.26(8) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 118.78(9) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 121.86(9) . . ?
C7 C8 O2 117.08(9) . . ?
C9 C8 O2 120.93(9) . . ?
C8 C9 C10 118.77(9) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C5 121.00(9) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 O2 123.38(9) . . ?
O1 C12 C11 126.16(10) . . ?
O2 C12 C11 110.46(9) . . ?
O4 C13 O3 124.04(8) . . ?
O4 C13 C2 126.27(8) . . ?
O3 C13 C2 109.63(8) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C5 C1 C2 C13 -124.29(8) . . . . ?
C2 C1 C2 C13 116.67(9) 3_566 . . . ?
C5 C1 C2 C1 119.04(9) . . . 3_566 ?
C2 C1 C2 C1 0.0 3_566 . . 3_566 ?
C2 C1 C5 C6 -34.36(12) . . . . ?
C2 C1 C5 C6 69.28(11) 3_566 . . . ?
C2 C1 C5 C10 150.51(9) . . . . ?
C2 C1 C5 C10 -105.86(10) 3_566 . . . ?
C10 C5 C6 C7 -0.39(14) . . . . ?
C1 C5 C6 C7 -175.63(9) . . . . ?
C5 C6 C7 C8 -0.17(15) . . . . ?
C6 C7 C8 C9 0.81(15) . . . . ?
C6 C7 C8 O2 176.67(8) . . . . ?
C12 O2 C8 C7 104.87(11) . . . . ?
C12 O2 C8 C9 -79.23(13) . . . . ?
C7 C8 C9 C10 -0.85(16) . . . . ?
O2 C8 C9 C10 -176.56(9) . . . . ?
C8 C9 C10 C5 0.27(15) . . . . ?
C6 C5 C10 C9 0.33(14) . . . . ?
C1 C5 C10 C9 175.59(9) . . . . ?
C8 O2 C12 O1 5.84(16) . . . . ?
C8 O2 C12 C11 -174.40(10) . . . . ?
C14 O3 C13 O4 -3.99(14) . . . . ?
C14 O3 C13 C2 173.31(9) . . . . ?
C1 C2 C13 O4 -4.28(13) . . . . ?
C1 C2 C13 O4 98.97(11) 3_566 . . . ?
C1 C2 C13 O3 178.50(7) . . . . ?
C1 C2 C13 O3 -78.25(9) 3_566 . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.67
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.057


_database_code_depnum_ccdc_archive 'CCDC 907651'