# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Charlotte Williams'
_publ_contact_author_email       C.K.WILLIAMS@IMPERIAL.AC.UK

_publ_section_title              
;
Biomaterials from sugars: ring-opening polymerization
of a carbohydrate lactone
;
loop_
_publ_author_name
'Charlotte Williams'
'Molly Stevens'
'Min Tang.'
'Andrew J P White'

# Attachment 'tang_et_al_supporting_information2.cif'

data_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 680953'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 O6'
_chemical_formula_sum            'C10 H14 O6'
_chemical_formula_weight         230.21

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                   7.19184(19)
_cell_length_b                   14.5149(4)
_cell_length_c                   11.0204(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.824(3)
_cell_angle_gamma                90
_cell_volume                     1112.11(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6683
_cell_measurement_theta_min      3.8156
_cell_measurement_theta_max      32.3027

_exptl_crystal_description       plates
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 15.9863
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16882
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         32.36
_reflns_number_total             3718
_reflns_number_gt                2332
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_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 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^)+(0.0754P)^2^+0.0000P] 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         3718
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.64602(15) 0.67165(8) 0.81943(9) 0.0270(2) Uani 1 1 d . . .
C2 C 0.80770(15) 0.70632(8) 0.76719(9) 0.0274(2) Uani 1 1 d . . .
H2A H 0.8746 0.7585 0.8200 0.033 Uiso 1 1 calc R . .
C3 C 0.72617(17) 0.73966(9) 0.63292(10) 0.0349(3) Uani 1 1 d . . .
H3A H 0.6829 0.6863 0.5769 0.042 Uiso 1 1 calc R . .
H3B H 0.8272 0.7724 0.6035 0.042 Uiso 1 1 calc R . .
C4 C 0.55498(17) 0.80505(8) 0.62778(10) 0.0324(3) Uani 1 1 d . . .
H4A H 0.5779 0.8643 0.5896 0.039 Uiso 1 1 calc R . .
H4B H 0.4362 0.7775 0.5741 0.039 Uiso 1 1 calc R . .
C5 C 0.52768(16) 0.82258(7) 0.75798(10) 0.0293(2) Uani 1 1 d . . .
H5A H 0.6420 0.8562 0.8098 0.035 Uiso 1 1 calc R . .
C6 C 0.34777(18) 0.87508(9) 0.75787(10) 0.0354(3) Uani 1 1 d . . .
H6A H 0.3390 0.9317 0.7065 0.042 Uiso 1 1 calc R . .
H6B H 0.2326 0.8367 0.7231 0.042 Uiso 1 1 calc R . .
C7 C 0.19818(17) 0.90525(8) 0.92395(11) 0.0336(3) Uani 1 1 d . . .
C8 C 0.2358(2) 0.92668(12) 1.05986(12) 0.0541(4) Uani 1 1 d . . .
H8A H 0.1595 0.9804 1.0713 0.081 Uiso 1 1 calc R . .
H8B H 0.3728 0.9401 1.0939 0.081 Uiso 1 1 calc R . .
H8C H 0.1999 0.8737 1.1040 0.081 Uiso 1 1 calc R . .
C9 C 1.06089(16) 0.61504(9) 0.88452(10) 0.0317(3) Uani 1 1 d . . .
C10 C 1.18401(17) 0.53401(9) 0.88232(11) 0.0377(3) Uani 1 1 d . . .
H10A H 1.2976 0.5529 0.8549 0.057 Uiso 1 1 calc R . .
H10B H 1.1115 0.4880 0.8239 0.057 Uiso 1 1 calc R . .
H10C H 1.2246 0.5074 0.9667 0.057 Uiso 1 1 calc R . .
O1 O 0.63285(12) 0.59565(6) 0.85880(8) 0.0375(2) Uani 1 1 d . . .
O2 O 0.50757(11) 0.73416(5) 0.81708(7) 0.0298(2) Uani 1 1 d . . .
O3 O 0.36123(12) 0.89828(6) 0.88806(7) 0.0408(2) Uani 1 1 d . . .
O4 O 0.04130(13) 0.89530(7) 0.85327(8) 0.0430(2) Uani 1 1 d . . .
O5 O 0.94154(11) 0.63294(6) 0.76908(7) 0.0325(2) Uani 1 1 d . . .
O6 O 1.06155(13) 0.66179(7) 0.97489(8) 0.0462(3) 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 0.0292(5) 0.0335(6) 0.0169(5) 0.0003(4) 0.0033(4) 0.0009(4)
C2 0.0270(5) 0.0323(6) 0.0222(5) 0.0010(4) 0.0049(4) 0.0019(4)
C3 0.0358(6) 0.0468(7) 0.0243(5) 0.0080(5) 0.0116(4) 0.0065(5)
C4 0.0362(6) 0.0376(6) 0.0240(5) 0.0061(4) 0.0088(4) 0.0034(5)
C5 0.0338(6) 0.0284(6) 0.0249(5) 0.0016(4) 0.0059(4) 0.0016(4)
C6 0.0390(6) 0.0410(7) 0.0236(5) -0.0022(4) 0.0035(4) 0.0090(5)
C7 0.0361(6) 0.0302(6) 0.0332(6) 0.0000(4) 0.0063(5) 0.0073(5)
C8 0.0547(8) 0.0723(10) 0.0349(7) -0.0089(6) 0.0105(6) 0.0203(7)
C9 0.0257(5) 0.0429(7) 0.0251(5) 0.0027(4) 0.0039(4) -0.0007(4)
C10 0.0335(6) 0.0466(8) 0.0311(6) 0.0035(5) 0.0046(5) 0.0058(5)
O1 0.0405(5) 0.0357(5) 0.0369(4) 0.0100(3) 0.0110(4) 0.0007(4)
O2 0.0319(4) 0.0341(5) 0.0254(4) 0.0063(3) 0.0107(3) 0.0035(3)
O3 0.0339(5) 0.0581(6) 0.0283(4) -0.0118(4) 0.0038(3) 0.0094(4)
O4 0.0348(5) 0.0502(6) 0.0417(5) -0.0025(4) 0.0054(4) -0.0017(4)
O5 0.0302(4) 0.0425(5) 0.0234(4) 0.0001(3) 0.0045(3) 0.0082(3)
O6 0.0456(5) 0.0605(6) 0.0268(4) -0.0073(4) -0.0011(4) 0.0123(4)

_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 1.1979(13) . ?
C1 O2 1.3424(13) . ?
C1 C2 1.5097(15) . ?
C2 O5 1.4322(13) . ?
C2 C3 1.5243(14) . ?
C3 C4 1.5441(16) . ?
C4 C5 1.5186(15) . ?
C5 O2 1.4630(13) . ?
C5 C6 1.5013(16) . ?
C6 O3 1.4527(13) . ?
C7 O4 1.2045(14) . ?
C7 O3 1.3338(14) . ?
C7 C8 1.4852(17) . ?
C9 O6 1.2040(14) . ?
C9 O5 1.3653(13) . ?
C9 C10 1.4762(17) . ?

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 O2 120.16(10) . . ?
O1 C1 C2 125.81(10) . . ?
O2 C1 C2 114.03(9) . . ?
O5 C2 C1 109.08(9) . . ?
O5 C2 C3 109.90(8) . . ?
C1 C2 C3 109.48(8) . . ?
C2 C3 C4 109.62(9) . . ?
C5 C4 C3 111.28(9) . . ?
O2 C5 C6 105.20(9) . . ?
O2 C5 C4 108.97(9) . . ?
C6 C5 C4 113.83(9) . . ?
O3 C6 C5 106.10(9) . . ?
O4 C7 O3 123.25(11) . . ?
O4 C7 C8 125.17(12) . . ?
O3 C7 C8 111.58(11) . . ?
O6 C9 O5 122.14(11) . . ?
O6 C9 C10 125.96(10) . . ?
O5 C9 C10 111.90(9) . . ?
C1 O2 C5 116.37(8) . . ?
C7 O3 C6 117.97(9) . . ?
C9 O5 C2 114.52(8) . . ?

_diffrn_measured_fraction_theta_max 0.935
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046

#===END