# Electronic Supplementary Material (ESI) for RSC Advances
# 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
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#  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.
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data_l0374a
#TrackingRef 'web_deposit_cif_file_0_MartinLutz_1351247259.deposit.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 O5'
_chemical_formula_sum            'C8 H8 O5'
_chemical_formula_weight         184.14

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   'C 2/c'
_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'
'-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                   15.2706(19)
_cell_length_b                   11.0750(13)
_cell_length_c                   11.6658(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.294(3)
_cell_angle_gamma                90.00
_cell_volume                     1667.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6857
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.40

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5846
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 Kappa ApexII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14085
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1563
_reflns_number_gt                1315
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       Apex2
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A, SADABS-2008/1'
_computing_structure_solution    'SIR-97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0671P)^2^+1.6627P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1563
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.015
_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
O1 O 0.39182(10) 0.24879(11) 0.01424(13) 0.0293(3) Uani 1 1 d . . .
O2 O 0.38484(11) 0.01836(12) 0.09882(13) 0.0355(4) Uani 1 1 d . . .
O3 O 0.35546(11) 0.09680(11) 0.25325(12) 0.0307(3) Uani 1 1 d . . .
O4 O 0.37398(11) 0.60397(12) 0.20246(14) 0.0359(4) Uani 1 1 d . . .
O5 O 0.38499(11) 0.62171(11) 0.01813(13) 0.0323(4) Uani 1 1 d . . .
C1 C 0.37316(13) 0.10329(15) 0.15327(17) 0.0256(4) Uani 1 1 d . . .
C2 C 0.37613(13) 0.23013(16) 0.11831(17) 0.0244(4) Uani 1 1 d . . .
C3 C 0.36740(13) 0.33666(15) 0.16791(17) 0.0250(4) Uani 1 1 d . . .
H3 H 0.3561 0.3483 0.2397 0.030 Uiso 1 1 calc R . .
C4 C 0.37867(13) 0.42807(16) 0.09059(17) 0.0252(4) Uani 1 1 d . . .
C5 C 0.39273(14) 0.37024(16) -0.00051(18) 0.0286(4) Uani 1 1 d . . .
H5 H 0.4020 0.4093 -0.0658 0.034 Uiso 1 1 calc R . .
C6 C 0.35321(18) -0.02495(17) 0.2981(2) 0.0370(5) Uani 1 1 d . . .
H6A H 0.3001 -0.0723 0.2212 0.055 Uiso 1 1 calc R . .
H6B H 0.3370 -0.0216 0.3688 0.055 Uiso 1 1 calc R . .
H6C H 0.4210 -0.0630 0.3347 0.055 Uiso 1 1 calc R . .
C7 C 0.37852(13) 0.55899(16) 0.11175(17) 0.0259(4) Uani 1 1 d . . .
C8 C 0.39205(17) 0.75194(16) 0.0357(2) 0.0384(5) Uani 1 1 d . . .
H8A H 0.3313 0.7816 0.0350 0.058 Uiso 1 1 calc R . .
H8B H 0.3946 0.7896 -0.0385 0.058 Uiso 1 1 calc R . .
H8C H 0.4550 0.7724 0.1225 0.058 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 0.0461(8) 0.0213(7) 0.0311(7) 0.0001(5) 0.0277(6) 0.0011(5)
O2 0.0594(9) 0.0223(7) 0.0361(7) -0.0014(5) 0.0330(7) 0.0024(6)
O3 0.0513(8) 0.0214(7) 0.0299(7) 0.0010(5) 0.0286(6) -0.0002(5)
O4 0.0584(9) 0.0249(7) 0.0375(8) -0.0032(5) 0.0343(7) -0.0010(6)
O5 0.0543(9) 0.0187(7) 0.0312(7) 0.0023(5) 0.0277(6) -0.0001(5)
C1 0.0317(9) 0.0235(9) 0.0239(8) -0.0001(7) 0.0164(8) 0.0002(7)
C2 0.0281(9) 0.0250(9) 0.0226(9) 0.0009(7) 0.0151(8) 0.0009(7)
C3 0.0311(9) 0.0227(9) 0.0247(8) 0.0003(7) 0.0173(7) 0.0011(7)
C4 0.0301(9) 0.0217(9) 0.0263(9) 0.0012(7) 0.0167(7) 0.0010(7)
C5 0.0402(10) 0.0224(9) 0.0302(9) 0.0027(7) 0.0235(8) 0.0002(7)
C6 0.0611(13) 0.0234(9) 0.0366(10) 0.0041(8) 0.0329(10) -0.0029(9)
C7 0.0308(9) 0.0222(9) 0.0262(9) 0.0011(7) 0.0162(8) 0.0004(7)
C8 0.0594(13) 0.0180(10) 0.0454(12) 0.0015(8) 0.0330(11) -0.0015(8)

_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 C5 1.357(2) . ?
O1 C2 1.373(2) . ?
O2 C1 1.200(2) . ?
O3 C1 1.332(2) . ?
O3 C6 1.454(2) . ?
O4 C7 1.205(2) . ?
O5 C7 1.342(2) . ?
O5 C8 1.453(2) . ?
C1 C2 1.470(2) . ?
C2 C3 1.352(2) . ?
C3 C4 1.426(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.353(2) . ?
C4 C7 1.471(2) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C5 O1 C2 106.24(13) . . ?
C1 O3 C6 114.85(14) . . ?
C7 O5 C8 115.54(14) . . ?
O2 C1 O3 125.30(16) . . ?
O2 C1 C2 124.51(16) . . ?
O3 C1 C2 110.19(14) . . ?
C3 C2 O1 110.55(15) . . ?
C3 C2 C1 133.67(16) . . ?
O1 C2 C1 115.78(15) . . ?
C2 C3 C4 106.02(15) . . ?
C2 C3 H3 127.0 . . ?
C4 C3 H3 127.0 . . ?
C5 C4 C3 106.51(15) . . ?
C5 C4 C7 127.86(16) . . ?
C3 C4 C7 125.59(15) . . ?
C4 C5 O1 110.67(15) . . ?
C4 C5 H5 124.7 . . ?
O1 C5 H5 124.7 . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 O5 124.39(17) . . ?
O4 C7 C4 124.13(16) . . ?
O5 C7 C4 111.48(14) . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C6 O3 C1 O2 1.4(3) . . . . ?
C6 O3 C1 C2 -178.71(15) . . . . ?
C5 O1 C2 C3 -0.01(19) . . . . ?
C5 O1 C2 C1 -179.52(15) . . . . ?
O2 C1 C2 C3 -178.25(19) . . . . ?
O3 C1 C2 C3 1.9(3) . . . . ?
O2 C1 C2 O1 1.1(3) . . . . ?
O3 C1 C2 O1 -178.73(14) . . . . ?
O1 C2 C3 C4 -0.22(19) . . . . ?
C1 C2 C3 C4 179.17(18) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C2 C3 C4 C7 -177.60(16) . . . . ?
C3 C4 C5 O1 -0.4(2) . . . . ?
C7 C4 C5 O1 177.52(16) . . . . ?
C2 O1 C5 C4 0.3(2) . . . . ?
C8 O5 C7 O4 3.2(3) . . . . ?
C8 O5 C7 C4 -176.23(16) . . . . ?
C5 C4 C7 O4 -173.59(18) . . . . ?
C3 C4 C7 O4 3.9(3) . . . . ?
C5 C4 C7 O5 5.9(3) . . . . ?
C3 C4 C7 O5 -176.61(16) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.054



#===END


_database_code_depnum_ccdc_archive 'CCDC 907968'