#######################################################################
#
#                 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.
# 
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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_xw10
_database_code_depnum_ccdc_archive 'CCDC 835399'
#TrackingRef 'xw10.cif'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C10 H14 N2 O6, 0.5(H2 O)'

_chemical_formula_sum            'C10 H15 N2 O6.50'

_chemical_formula_weight         267.24




_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'
N N 0.0061 0.0033 '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           Orthorhombic

_symmetry_space_group_name_H-M   P2(1)2(1)2(1)




_symmetry_equiv_pos_as_xyz




'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'



_cell_length_a                   13.9973(5)

_cell_length_b                   17.2440(6)

_cell_length_c                   4.8028(2)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1159.25(8)

_cell_formula_units_Z            4

_cell_measurement_temperature    100(2)

_cell_measurement_reflns_used    9892

_cell_measurement_theta_min      2.77

_cell_measurement_theta_max      30.46



_exptl_crystal_description       Block

_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.34

_exptl_crystal_size_mid          0.33

_exptl_crystal_size_min          0.26

_exptl_crystal_density_meas      .

_exptl_crystal_density_diffrn    1.531

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             564

_exptl_absorpt_coefficient_mu    0.129

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  0.9573

_exptl_absorpt_correction_T_max  0.9672

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

?

;



_diffrn_ambient_temperature      100(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 SMART 1000'

_diffrn_measurement_method       '\w scans at 9 \f settings'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            30650

_diffrn_reflns_av_R_equivalents  0.0432

_diffrn_reflns_av_sigmaI/netI    0.0184

_diffrn_reflns_limit_h_min       -19

_diffrn_reflns_limit_h_max       19

_diffrn_reflns_limit_k_min       -24

_diffrn_reflns_limit_k_max       24

_diffrn_reflns_limit_l_min       -6

_diffrn_reflns_limit_l_max       6

_diffrn_reflns_theta_min         1.87

_diffrn_reflns_theta_max         30.52

_reflns_number_total             3535

_reflns_number_gt                3342

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART v5.630'

_computing_cell_refinement       'Bruker SAINT-Plus v7.66A'

_computing_data_reduction        'Bruker SAINT-Plus v7.66A'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    'Bruker XP v5.1'

_computing_publication_material  'Bruker XCIF 2008'



_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 matrix'
_refine_ls_weighting_scheme      Sigma
_refine_ls_weighting_details     w=1/s^2^(Fo^2^)
_atom_sites_solution_primary     'Direct methods'
_atom_sites_solution_secondary   'Difference Fourier map'
_atom_sites_solution_hydrogens   'Difference Fourier map'
_refine_ls_hydrogen_treatment    Unrestrained
_chemical_absolute_configuration ?
_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   -0.3(6)

_refine_ls_number_reflns         3535

_refine_ls_number_parameters     228

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0343

_refine_ls_R_factor_gt           0.0318

_refine_ls_wR_factor_ref         0.0558

_refine_ls_wR_factor_gt          0.0554

_refine_ls_goodness_of_fit_ref   2.877

_refine_ls_restrained_S_all      2.877

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000




_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 0.79142(5) 0.34093(4) 0.71108(16) 0.01332(16) Uani 1 1 d . . .
O2 O 0.63185(6) 0.41169(5) 0.39154(18) 0.01589(17) Uani 1 1 d . . .
O3 O 0.87561(6) 0.50776(5) 0.32991(17) 0.01588(17) Uani 1 1 d . . .
O4 O 0.99160(6) 0.40749(5) 0.63228(18) 0.01758(18) Uani 1 1 d . . .
O5 O 0.99355(6) 0.19022(5) 0.45507(18) 0.01796(18) Uani 1 1 d . . .
O6 O 0.78819(6) 0.07838(5) -0.15967(18) 0.02026(19) Uani 1 1 d . . .
N1 N 0.84704(6) 0.24595(5) 0.3956(2) 0.01195(19) Uani 1 1 d . . .
N2 N 0.88821(7) 0.13549(5) 0.1479(2) 0.0138(2) Uani 1 1 d . . .
C1 C 0.78396(8) 0.42292(6) 0.6431(2) 0.0114(2) Uani 1 1 d . . .
C2 C 0.68002(8) 0.44567(7) 0.6257(3) 0.0152(2) Uani 1 1 d . . .
C3 C 0.84323(7) 0.43115(6) 0.3794(2) 0.0107(2) Uani 1 1 d . . .
C4 C 0.92648(8) 0.37609(6) 0.4383(2) 0.0125(2) Uani 1 1 d . . .
C5 C 0.87516(8) 0.30958(6) 0.5887(2) 0.0117(2) Uani 1 1 d . . .
C6 C 0.91484(7) 0.19005(6) 0.3415(2) 0.0126(2) Uani 1 1 d . . .
C7 C 0.80123(8) 0.13136(6) 0.0103(2) 0.0136(2) Uani 1 1 d . . .
C8 C 0.73327(7) 0.19118(6) 0.0782(2) 0.0122(2) Uani 1 1 d . . .
C9 C 0.63753(8) 0.19190(7) -0.0634(3) 0.0166(2) Uani 1 1 d . . .
C10 C 0.75927(8) 0.24572(7) 0.2641(2) 0.0122(2) Uani 1 1 d . . .
H1N H 0.9302(10) 0.1000(8) 0.109(3) 0.026(4) Uiso 1 1 d . . .
H1 H 0.8148(8) 0.4527(7) 0.793(3) 0.010(3) Uiso 1 1 d . . .
H2 H 0.5918(12) 0.3816(10) 0.454(4) 0.047(5) Uiso 1 1 d . . .
H3 H 0.8274(11) 0.5338(9) 0.275(3) 0.037(5) Uiso 1 1 d . . .
H4 H 1.0307(11) 0.4374(8) 0.537(4) 0.035(5) Uiso 1 1 d . . .
H5 H 0.9155(8) 0.2857(7) 0.734(3) 0.011(3) Uiso 1 1 d . . .
H10 H 0.7204(9) 0.2876(7) 0.322(3) 0.010(3) Uiso 1 1 d . . .
H2A H 0.6485(9) 0.4336(7) 0.799(3) 0.014(3) Uiso 1 1 d . . .
H3A H 0.8062(8) 0.4108(6) 0.223(2) 0.003(3) Uiso 1 1 d . . .
H4A H 0.9576(8) 0.3567(6) 0.270(3) 0.008(3) Uiso 1 1 d . . .
H9A H 0.5993(9) 0.1468(8) -0.009(3) 0.027(4) Uiso 1 1 d . . .
H2B H 0.6769(8) 0.5044(7) 0.602(2) 0.009(3) Uiso 1 1 d . . .
H9B H 0.6452(9) 0.1876(8) -0.260(3) 0.027(4) Uiso 1 1 d . . .
H9C H 0.6007(10) 0.2408(9) -0.015(3) 0.030(4) Uiso 1 1 d . . .
O11 O 0.5000 0.5000 0.0594(3) 0.0161(2) Uani 1 2 d S . .
H11 H 0.5453(10) 0.4811(9) 0.172(3) 0.045(5) Uiso 1 1 d . . .




_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 0.0155(4) 0.0095(4) 0.0150(4) 0.0018(3) 0.0038(3) 0.0003(3)
O2 0.0127(4) 0.0158(4) 0.0193(4) 0.0016(4) 0.0001(3) -0.0030(3)
O3 0.0140(4) 0.0116(4) 0.0221(4) 0.0060(3) -0.0008(3) -0.0017(3)
O4 0.0142(4) 0.0152(4) 0.0233(4) 0.0026(4) -0.0073(3) -0.0043(3)
O5 0.0130(4) 0.0154(4) 0.0255(4) -0.0019(4) -0.0044(3) 0.0025(3)
O6 0.0186(4) 0.0171(4) 0.0251(5) -0.0083(4) -0.0029(4) 0.0004(3)
N1 0.0116(4) 0.0087(4) 0.0155(5) -0.0010(4) -0.0015(4) 0.0004(3)
N2 0.0115(5) 0.0107(4) 0.0193(5) -0.0025(4) 0.0001(4) 0.0022(4)
C1 0.0149(5) 0.0080(5) 0.0112(5) 0.0003(4) 0.0014(4) -0.0005(4)
C2 0.0150(5) 0.0148(6) 0.0156(6) -0.0012(5) 0.0028(5) 0.0012(4)
C3 0.0104(5) 0.0094(5) 0.0123(5) 0.0005(4) 0.0006(4) -0.0017(4)
C4 0.0106(5) 0.0121(5) 0.0148(6) 0.0002(4) -0.0001(4) -0.0012(4)
C5 0.0123(5) 0.0102(5) 0.0125(5) -0.0006(4) -0.0021(4) 0.0007(4)
C6 0.0121(5) 0.0095(5) 0.0163(6) 0.0027(5) 0.0004(4) -0.0012(4)
C7 0.0136(5) 0.0127(5) 0.0147(5) 0.0022(4) 0.0005(4) -0.0025(4)
C8 0.0116(5) 0.0107(5) 0.0142(5) 0.0012(4) -0.0005(4) -0.0013(4)
C9 0.0139(6) 0.0176(6) 0.0183(6) -0.0023(5) -0.0034(5) 0.0000(5)
C10 0.0097(5) 0.0121(5) 0.0149(5) 0.0022(4) 0.0007(4) 0.0014(4)
O11 0.0124(6) 0.0173(6) 0.0185(6) 0.000 0.000 0.0022(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.

;




_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 1.4183(13) . ?
O1 C1 1.4550(13) . ?
O2 C2 1.4361(15) . ?
O2 H2 0.820(17) . ?
O3 C3 1.4167(13) . ?
O3 H3 0.853(15) . ?
O4 C4 1.4115(13) . ?
O4 H4 0.879(16) . ?
O5 C6 1.2293(13) . ?
O6 C7 1.2387(14) . ?
N1 C6 1.3775(14) . ?
N1 C10 1.3812(14) . ?
N1 C5 1.4897(14) . ?
N2 C6 1.3743(14) . ?
N2 C7 1.3871(14) . ?
N2 H1N 0.868(14) . ?
C1 C2 1.5093(16) . ?
C1 C3 1.5204(15) . ?
C1 H1 0.985(12) . ?
C2 H2A 0.964(13) . ?
C2 H2B 1.021(12) . ?
C3 C4 1.5294(15) . ?
C3 H3A 0.976(11) . ?
C4 C5 1.5343(15) . ?
C4 H4A 0.975(12) . ?
C5 H5 0.988(12) . ?
C7 C8 1.4406(15) . ?
C8 C10 1.3469(16) . ?
C8 C9 1.5029(15) . ?
C9 H9A 0.979(14) . ?
C9 H9B 0.953(15) . ?
C9 H9C 1.016(15) . ?
C10 H10 0.946(12) . ?
O11 H11 0.895(15) . ?




_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 C1 109.68(8) . . ?
C2 O2 H2 107.1(13) . . ?
C3 O3 H3 106.8(10) . . ?
C4 O4 H4 106.5(11) . . ?
C6 N1 C10 121.64(9) . . ?
C6 N1 C5 116.79(8) . . ?
C10 N1 C5 121.45(9) . . ?
C6 N2 C7 126.55(10) . . ?
C6 N2 H1N 116.3(10) . . ?
C7 N2 H1N 117.1(10) . . ?
O1 C1 C2 109.52(9) . . ?
O1 C1 C3 103.80(8) . . ?
C2 C1 C3 117.11(10) . . ?
O1 C1 H1 108.1(7) . . ?
C2 C1 H1 109.1(7) . . ?
C3 C1 H1 108.8(7) . . ?
O2 C2 C1 112.95(9) . . ?
O2 C2 H2A 111.8(7) . . ?
C1 C2 H2A 109.7(8) . . ?
O2 C2 H2B 107.2(6) . . ?
C1 C2 H2B 107.8(6) . . ?
H2A C2 H2B 107.0(10) . . ?
O3 C3 C1 113.67(9) . . ?
O3 C3 C4 111.47(9) . . ?
C1 C3 C4 101.77(9) . . ?
O3 C3 H3A 112.1(6) . . ?
C1 C3 H3A 108.4(6) . . ?
C4 C3 H3A 108.9(6) . . ?
O4 C4 C3 112.07(9) . . ?
O4 C4 C5 106.15(9) . . ?
C3 C4 C5 101.20(8) . . ?
O4 C4 H4A 112.9(7) . . ?
C3 C4 H4A 113.6(7) . . ?
C5 C4 H4A 110.0(7) . . ?
O1 C5 N1 108.68(8) . . ?
O1 C5 C4 107.29(9) . . ?
N1 C5 C4 112.40(9) . . ?
O1 C5 H5 109.8(7) . . ?
N1 C5 H5 106.5(7) . . ?
C4 C5 H5 112.2(7) . . ?
O5 C6 N2 123.02(10) . . ?
O5 C6 N1 122.15(10) . . ?
N2 C6 N1 114.82(9) . . ?
O6 C7 N2 118.76(10) . . ?
O6 C7 C8 125.45(10) . . ?
N2 C7 C8 115.79(10) . . ?
C10 C8 C7 118.14(10) . . ?
C10 C8 C9 122.36(10) . . ?
C7 C8 C9 119.49(10) . . ?
C8 C9 H9A 111.1(8) . . ?
C8 C9 H9B 110.3(8) . . ?
H9A C9 H9B 105.2(12) . . ?
C8 C9 H9C 110.8(8) . . ?
H9A C9 H9C 108.7(11) . . ?
H9B C9 H9C 110.5(12) . . ?
C8 C10 N1 123.05(10) . . ?
C8 C10 H10 124.9(7) . . ?
N1 C10 H10 112.0(7) . . ?




_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





N2 H1N O11 0.868(14) 2.142(14) 2.9830(10) 163.2(13) 3
O2 H2 O5 0.820(17) 1.902(17) 2.7163(11) 171.9(18) 3_456
O3 H3 O6 0.853(15) 1.875(16) 2.7219(12) 172.1(15) 4_655
O4 H4 O3 0.879(16) 1.899(16) 2.7748(11) 173.7(14) 2_765
O11 H11 O2 0.895(15) 2.003(15) 2.8756(10) 164.7(15) .



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        30.52

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.269

_refine_diff_density_min         -0.273

_refine_diff_density_rms         0.052