# 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_p
#TrackingRef '18736_web_deposit_cif_file_0_ZhenghuXu_1363854400.bifuran.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 O8'
_chemical_formula_weight         422.46

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           ?
_symmetry_space_group_name_H-M   ?

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'
'-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                   22.579(7)
_cell_length_b                   4.8945(14)
_cell_length_c                   22.195(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.560(4)
_cell_angle_gamma                90.00
_cell_volume                     2296.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9862
_exptl_absorpt_correction_T_max  0.9908
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5338
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2015
_reflns_number_gt                1350
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of 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^)+(0.0581P)^2^+0.5440P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2015
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.10951(9) 0.2801(4) -0.01775(10) 0.0475(5) Uani 1 1 d . . .
C2 C 0.06488(9) 0.1308(4) -0.06294(9) 0.0446(5) Uani 1 1 d . . .
C3 C 0.00456(9) 0.2192(4) -0.05989(9) 0.0417(5) Uani 1 1 d . . .
C4 C 0.01797(8) 0.4157(4) -0.01403(9) 0.0397(5) Uani 1 1 d . . .
C5 C 0.20716(11) 0.4767(6) 0.04705(13) 0.0878(9) Uani 1 1 d . . .
H5A H 0.1934 0.6570 0.0313 0.132 Uiso 1 1 calc R . .
H5B H 0.2515 0.4580 0.0543 0.132 Uiso 1 1 calc R . .
H5C H 0.2000 0.4474 0.0867 0.132 Uiso 1 1 calc R . .
C6 C 0.07769(11) -0.0710(4) -0.10532(10) 0.0563(6) Uani 1 1 d . . .
C7 C -0.05945(10) 0.1065(5) -0.09890(10) 0.0487(5) Uani 1 1 d . . .
H7A H -0.0877(10) 0.127(4) -0.0739(10) 0.058 Uiso 1 1 d . . .
H7B H -0.0543(9) -0.102(4) -0.1048(9) 0.058 Uiso 1 1 d . . .
C8 C -0.09016(11) 0.2368(5) -0.16479(11) 0.0611(6) Uani 1 1 d . . .
H8A H -0.0927(10) 0.439(5) -0.1608(10) 0.073 Uiso 1 1 d . . .
H8B H -0.0606(11) 0.228(4) -0.1895(10) 0.073 Uiso 1 1 d . . .
C9 C -0.15455(13) 0.1138(7) -0.20115(14) 0.0824(9) Uani 1 1 d . . .
H9A H -0.1471(13) -0.083(6) -0.2058(13) 0.099 Uiso 1 1 d . . .
H9B H -0.1823(13) 0.145(6) -0.1773(13) 0.099 Uiso 1 1 d . . .
C10 C -0.18551(14) 0.2263(7) -0.26776(14) 0.1176(13) Uani 1 1 d . . .
H10A H -0.1592 0.1903 -0.2928 0.176 Uiso 1 1 calc R . .
H10B H -0.1911 0.4199 -0.2654 0.176 Uiso 1 1 calc R . .
H10C H -0.2260 0.1407 -0.2877 0.176 Uiso 1 1 calc R . .
C11 C 0.0435(2) -0.3504(11) -0.1951(2) 0.0760(15) Uani 0.50 1 d P . .
H11A H 0.0047 -0.3899 -0.2296 0.114 Uiso 0.50 1 calc PR . .
H11B H 0.0618 -0.5173 -0.1740 0.114 Uiso 0.50 1 calc PR . .
H11C H 0.0725 -0.2632 -0.2120 0.114 Uiso 0.50 1 calc PR . .
C11A C 0.1455(3) -0.3415(11) -0.1361(3) 0.0834(16) Uani 0.50 1 d P . .
H11D H 0.1320 -0.2762 -0.1796 0.125 Uiso 0.50 1 calc PR . .
H11E H 0.1222 -0.5031 -0.1342 0.125 Uiso 0.50 1 calc PR . .
H11F H 0.1899 -0.3834 -0.1216 0.125 Uiso 0.50 1 calc PR . .
O1 O 0.08349(6) 0.4564(3) 0.01284(6) 0.0469(4) Uani 1 1 d . . .
O2 O 0.17218(6) 0.2783(3) 0.00035(7) 0.0673(5) Uani 1 1 d . . .
O5 O 0.03105(8) -0.1734(4) -0.15007(8) 0.0763(5) Uani 1 1 d . . .
O9 O 0.13448(8) -0.1367(4) -0.09590(8) 0.0821(6) 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 0.0364(12) 0.0564(13) 0.0514(12) 0.0005(10) 0.0173(10) 0.0062(9)
C2 0.0416(12) 0.0506(12) 0.0427(11) 0.0000(9) 0.0161(9) 0.0025(9)
C3 0.0374(11) 0.0465(11) 0.0399(10) 0.0026(9) 0.0118(8) 0.0003(8)
C4 0.0280(10) 0.0479(12) 0.0410(11) 0.0023(9) 0.0093(8) 0.0002(8)
C5 0.0395(14) 0.121(2) 0.094(2) -0.0400(18) 0.0119(13) -0.0075(14)
C6 0.0617(15) 0.0566(14) 0.0516(13) 0.0013(11) 0.0211(12) 0.0060(11)
C7 0.0415(12) 0.0527(13) 0.0508(13) -0.0052(10) 0.0147(10) -0.0052(10)
C8 0.0508(14) 0.0628(16) 0.0584(15) 0.0005(12) 0.0053(11) -0.0002(11)
C9 0.0589(17) 0.099(2) 0.0670(17) -0.0130(16) -0.0057(13) -0.0011(15)
C10 0.081(2) 0.154(3) 0.083(2) -0.012(2) -0.0148(17) 0.012(2)
C11 0.088(4) 0.083(4) 0.062(3) -0.021(3) 0.032(3) -0.004(3)
C11A 0.092(4) 0.077(3) 0.102(4) -0.025(3) 0.061(3) 0.005(3)
O1 0.0329(8) 0.0551(8) 0.0507(8) -0.0070(6) 0.0121(6) 0.0006(6)
O2 0.0346(9) 0.0865(12) 0.0781(11) -0.0226(9) 0.0164(7) 0.0030(7)
O5 0.0654(11) 0.0915(13) 0.0685(11) -0.0293(10) 0.0191(9) 0.0021(9)
O9 0.0573(11) 0.0953(13) 0.0962(13) -0.0344(10) 0.0301(9) 0.0104(9)

_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 O2 1.328(2) . ?
C1 O1 1.353(2) . ?
C1 C2 1.359(3) . ?
C2 C3 1.453(3) . ?
C2 C6 1.461(3) . ?
C3 C4 1.355(3) . ?
C3 C7 1.505(3) . ?
C4 O1 1.402(2) . ?
C4 C4 1.443(4) 5_565 ?
C5 O2 1.437(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O9 1.266(3) . ?
C6 O5 1.270(3) . ?
C7 C8 1.521(3) . ?
C7 H7A 0.99(2) . ?
C7 H7B 1.04(2) . ?
C8 C9 1.518(3) . ?
C8 H8A 1.00(2) . ?
C8 H8B 1.00(2) . ?
C9 C10 1.501(4) . ?
C9 H9A 0.99(3) . ?
C9 H9B 0.96(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O5 1.423(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11A O9 1.421(5) . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 117.16(17) . . ?
O2 C1 C2 130.91(19) . . ?
O1 C1 C2 111.92(17) . . ?
C1 C2 C3 105.65(17) . . ?
C1 C2 C6 125.15(19) . . ?
C3 C2 C6 129.19(18) . . ?
C4 C3 C2 106.29(16) . . ?
C4 C3 C7 127.48(18) . . ?
C2 C3 C7 126.20(18) . . ?
C3 C4 O1 110.16(15) . . ?
C3 C4 C4 136.0(2) . 5_565 ?
O1 C4 C4 113.85(19) . 5_565 ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O9 C6 O5 122.9(2) . . ?
O9 C6 C2 118.9(2) . . ?
O5 C6 C2 118.2(2) . . ?
C3 C7 C8 114.89(18) . . ?
C3 C7 H7A 108.6(12) . . ?
C8 C7 H7A 109.3(12) . . ?
C3 C7 H7B 107.7(11) . . ?
C8 C7 H7B 108.9(11) . . ?
H7A C7 H7B 107.1(16) . . ?
C9 C8 C7 111.9(2) . . ?
C9 C8 H8A 111.5(13) . . ?
C7 C8 H8A 110.6(13) . . ?
C9 C8 H8B 112.9(13) . . ?
C7 C8 H8B 110.0(13) . . ?
H8A C8 H8B 99.4(19) . . ?
C10 C9 C8 114.0(3) . . ?
C10 C9 H9A 107.0(16) . . ?
C8 C9 H9A 106.0(16) . . ?
C10 C9 H9B 108.4(17) . . ?
C8 C9 H9B 109.3(17) . . ?
H9A C9 H9B 112(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O9 C11A H11D 109.5 . . ?
O9 C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
O9 C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C1 O1 C4 105.97(14) . . ?
C1 O2 C5 118.09(17) . . ?
C6 O5 C11 118.4(3) . . ?
C6 O9 C11A 117.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034


_database_code_depnum_ccdc_archive 'CCDC 930435'