# 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_111028_s1_mxf
#TrackingRef '16017_web_deposit_cif_file_0_XiaofengMa_1355064798.111028_s1_mxf.cif'

_audit_creation_date             2011-11-01
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.09.07 svn.r1971, GUI svn.r3853)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C12 H22 O5'
_chemical_formula_sum            'C12 H22 O5'
_chemical_formula_weight         246.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O5
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   6.2466(4)
_cell_length_b                   6.8285(6)
_cell_length_c                   16.0444(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.122(8)
_cell_angle_gamma                90.00
_cell_volume                     682.60(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    771
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1985
_cell_measurement_theta_min      3.2371
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
?
;
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2891
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.24
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega 13.00 50.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -17.0486 77.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
2 omega -47.00 -15.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -17.0486 77.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
3 omega -9.00 56.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 20.0174 77.0000 60.0000 65

#__ type_ start__ end____ width___ exp.time_
4 omega -4.00 82.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 20.0174 77.0000 -60.0000 86

#__ type_ start__ end____ width___ exp.time_
5 omega -52.00 -27.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 20.0174 -38.0000 -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0643024000
_diffrn_orient_matrix_UB_12      0.0443384000
_diffrn_orient_matrix_UB_13      -0.0330255000
_diffrn_orient_matrix_UB_21      0.0918427000
_diffrn_orient_matrix_UB_22      0.0111806000
_diffrn_orient_matrix_UB_23      -0.0230931000
_diffrn_orient_matrix_UB_31      -0.0195638000
_diffrn_orient_matrix_UB_32      -0.0933096000
_diffrn_orient_matrix_UB_33      -0.0184504000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1356
_reflns_number_total             2004
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2004
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0748
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          11.287
_refine_ls_shift/su_mean         0.057
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1299P)²+0.0869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1934
_refine_ls_wR_factor_ref         0.2271
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 -0.9621(5) -0.9593(6) -0.3437(2) 0.0725(12) Uani 1 1 d . . .
O2 O -0.7980(6) -1.0604(8) -0.2172(2) 0.0861(13) Uani 1 1 d . . .
O3 O -0.3535(5) -1.0647(7) -0.4156(2) 0.0747(11) Uani 1 1 d . . .
H3 H -0.2442 -0.9988 -0.4077 0.112 Uiso 1 1 calc R . .
O4 O -0.5302(5) -0.6776(6) -0.4280(3) 0.0763(12) Uani 1 1 d . . .
H4 H -0.582(10) -0.624(11) -0.486(5) 0.10(2) Uiso 1 1 d . . .
O5 O -1.1339(8) -0.5659(10) -0.3556(4) 0.128(2) Uani 1 1 d . . .
H5 H -1.2439 -0.6318 -0.3583 0.192 Uiso 1 1 calc R . .
C1 C -0.5139(7) -0.9932(8) -0.3644(3) 0.0563(13) Uani 1 1 d . . .
H1 H -0.439(7) -0.925(6) -0.310(3) 0.047(12) Uiso 1 1 d . . .
C2 C -0.6560(7) -0.8469(8) -0.4124(4) 0.0592(13) Uani 1 1 d . . .
H2 H -0.699(7) -0.902(7) -0.467(3) 0.045(11) Uiso 1 1 d . . .
C3 C -0.8395(7) -0.7888(8) -0.3594(4) 0.0650(15) Uani 1 1 d . . .
H3A H -0.784(8) -0.733(8) -0.300(3) 0.066(14) Uiso 1 1 d . . .
C4 C -0.8481(8) -1.1145(9) -0.3010(4) 0.0713(15) Uani 1 1 d . . .
H4A H -1.001(12) -1.228(12) -0.321(5) 0.12(2) Uiso 1 1 d . . .
C5 C -0.6390(7) -1.1685(9) -0.3358(4) 0.0623(14) Uani 1 1 d . . .
H5A H -0.666(8) -1.253(9) -0.387(3) 0.068(15) Uiso 1 1 d . . .
C6 C -0.5262(11) -1.2730(12) -0.2599(4) 0.0882(19) Uani 1 1 d . . .
H6A H -0.546(11) -1.432(10) -0.261(4) 0.093(19) Uiso 1 1 d . . .
H6B H -0.352(9) -1.246(8) -0.263(3) 0.067(14) Uiso 1 1 d . . .
C7 C -0.6219(11) -1.1825(14) -0.1834(4) 0.104(3) Uani 1 1 d . . .
C8 C -0.9904(8) -0.6464(9) -0.4047(4) 0.0773(18) Uani 1 1 d . . .
H8A H -1.089(4) -0.706(4) -0.4608(16) 0.000(6) Uiso 1 1 d . . .
H8B H -0.904(8) -0.521(9) -0.425(3) 0.062(14) Uiso 1 1 d . . .
C9 C -0.4672(16) -1.044(3) -0.1346(5) 0.164(5) Uani 1 1 d . . .
H9A H -0.4008 -0.9587 -0.1728 0.246 Uiso 1 1 calc R . .
H9B H -0.3588 -1.1184 -0.1034 0.246 Uiso 1 1 calc R . .
H9C H -0.5450 -0.9665 -0.0969 0.246 Uiso 1 1 calc R . .
C10 C -0.695(2) -1.311(3) -0.1167(7) 0.166(5) Uani 1 1 d . . .
H10A H -0.5755 -1.3887 -0.0935 0.200 Uiso 1 1 calc R . .
H10B H -0.7455 -1.2307 -0.0722 0.200 Uiso 1 1 calc R . .
C11 C -0.855(3) -1.431(2) -0.1457(9) 0.207(7) Uani 1 1 d . . .
H11A H -0.8042 -1.5075 -0.1914 0.248 Uiso 1 1 calc R . .
H11B H -0.9738 -1.3518 -0.1684 0.248 Uiso 1 1 calc R . .
C12 C -0.946(2) -1.586(3) -0.0753(7) 0.218(8) Uani 1 1 d . . .
H12A H -0.8494 -1.6948 -0.0674 0.327 Uiso 1 1 calc R . .
H12B H -1.0857 -1.6332 -0.0950 0.327 Uiso 1 1 calc R . .
H12C H -0.9562 -1.5191 -0.0231 0.327 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 0.0301(15) 0.080(3) 0.107(3) 0.008(2) -0.0027(16) -0.0057(18)
O2 0.074(2) 0.107(3) 0.078(2) 0.003(3) 0.0113(19) 0.013(3)
O3 0.0303(15) 0.100(3) 0.094(2) -0.016(2) 0.0054(15) -0.0001(18)
O4 0.0417(17) 0.092(3) 0.094(3) 0.012(2) -0.0051(18) -0.022(2)
O5 0.076(3) 0.134(5) 0.170(5) -0.036(5) -0.013(3) 0.006(4)
C1 0.031(2) 0.070(3) 0.066(3) -0.010(3) -0.004(2) -0.002(2)
C2 0.038(2) 0.068(3) 0.071(3) -0.005(3) -0.002(2) -0.013(3)
C3 0.031(2) 0.066(3) 0.097(4) -0.004(3) -0.005(2) -0.006(2)
C4 0.045(2) 0.080(4) 0.088(4) 0.007(3) 0.001(2) -0.006(3)
C5 0.043(2) 0.071(3) 0.072(3) 0.001(3) -0.002(2) -0.004(3)
C6 0.073(4) 0.096(5) 0.096(4) 0.014(4) 0.009(3) 0.019(4)
C7 0.086(4) 0.143(7) 0.082(4) 0.022(5) -0.002(4) 0.021(5)
C8 0.041(2) 0.067(4) 0.126(5) 0.005(4) 0.016(3) 0.005(3)
C9 0.145(8) 0.226(13) 0.114(6) -0.048(8) -0.043(6) 0.031(10)
C10 0.167(10) 0.201(12) 0.128(8) -0.008(9) -0.006(7) 0.054(11)
C11 0.269(17) 0.166(12) 0.169(11) 0.034(10) -0.086(12) -0.020(13)
C12 0.247(15) 0.27(2) 0.140(8) 0.062(12) 0.041(9) -0.054(15)

_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 1.426(7) . ?
O1 C4 1.424(7) . ?
O2 C4 1.407(7) . ?
O2 C7 1.454(8) . ?
O3 H3 0.8200 . ?
O3 C1 1.427(6) . ?
O4 H4 1.03(8) . ?
O4 C2 1.430(6) . ?
O5 H5 0.8200 . ?
O5 C8 1.352(8) . ?
C1 H1 1.06(4) . ?
C1 C2 1.511(7) . ?
C1 C5 1.518(8) . ?
C2 H2 0.98(4) . ?
C2 C3 1.529(7) . ?
C3 H3A 1.06(5) . ?
C3 C8 1.505(8) . ?
C4 H4A 1.26(8) . ?
C4 C5 1.503(7) . ?
C5 H5A 1.01(6) . ?
C5 C6 1.539(9) . ?
C6 H6A 1.09(7) . ?
C6 H6B 1.11(5) . ?
C6 C7 1.533(11) . ?
C7 C9 1.529(14) . ?
C7 C10 1.482(15) . ?
C8 H8A 1.13(3) . ?
C8 H8B 1.07(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.347(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.68(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C4 O1 C3 115.8(3) . . ?
C4 O2 C7 108.4(5) . . ?
C1 O3 H3 109.5 . . ?
C2 O4 H4 108(4) . . ?
C8 O5 H5 109.5 . . ?
O3 C1 H1 109(2) . . ?
O3 C1 C2 110.1(4) . . ?
O3 C1 C5 107.6(5) . . ?
C2 C1 H1 110(2) . . ?
C2 C1 C5 112.3(3) . . ?
C5 C1 H1 108(2) . . ?
O4 C2 C1 108.3(4) . . ?
O4 C2 H2 106(3) . . ?
O4 C2 C3 109.3(4) . . ?
C1 C2 H2 109(3) . . ?
C1 C2 C3 108.9(4) . . ?
C3 C2 H2 116(3) . . ?
O1 C3 C2 108.7(4) . . ?
O1 C3 H3A 106(3) . . ?
O1 C3 C8 106.7(4) . . ?
C2 C3 H3A 113(3) . . ?
C8 C3 C2 111.6(5) . . ?
C8 C3 H3A 111(3) . . ?
O1 C4 H4A 89(4) . . ?
O1 C4 C5 114.9(5) . . ?
O2 C4 O1 109.5(5) . . ?
O2 C4 H4A 122(3) . . ?
O2 C4 C5 106.3(4) . . ?
C5 C4 H4A 115(4) . . ?
C1 C5 H5A 105(3) . . ?
C1 C5 C6 112.8(5) . . ?
C4 C5 C1 113.5(5) . . ?
C4 C5 H5A 110(3) . . ?
C4 C5 C6 100.4(5) . . ?
C6 C5 H5A 115(3) . . ?
C5 C6 H6A 114(4) . . ?
C5 C6 H6B 106(3) . . ?
H6A C6 H6B 106(5) . . ?
C7 C6 C5 105.3(5) . . ?
C7 C6 H6A 111(4) . . ?
C7 C6 H6B 114(3) . . ?
O2 C7 C6 105.1(5) . . ?
O2 C7 C9 105.6(8) . . ?
O2 C7 C10 110.1(7) . . ?
C9 C7 C6 113.1(7) . . ?
C10 C7 C6 119.9(8) . . ?
C10 C7 C9 102.4(9) . . ?
O5 C8 C3 113.5(6) . . ?
O5 C8 H8A 105.2(14) . . ?
O5 C8 H8B 103(3) . . ?
C3 C8 H8A 116.2(15) . . ?
C3 C8 H8B 110(3) . . ?
H8A C8 H8B 108(3) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.3 . . ?
C7 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C7 111.7(10) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C10 C11 C12 115.5(11) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.82 1.99 2.725(4) 148.2 1_655
O4 H4 O3 1.03(8) 1.65(8) 2.676(6) 172(6) 2_454
O5 H5 O4 0.82 2.06 2.765(6) 143.4 1_455



_database_code_depnum_ccdc_archive 'CCDC 851788'
