data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Jonathan White'
'Nathan Fifer'

_publ_contact_author_name        'Dr Jonathan White'
_publ_contact_author_address     
;
School of Chemistry and BIO-21 Institute
University of Melbourne
30 Flemington Road
Parkville
Melbourne
Vic
3150
AUSTRALIA
;

_publ_contact_author_email       WHITEJM@UNIMELB.EDU.AU

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Determining the s-Donor Ability of the Cyclopropane
C-C bond.
;

data_jmwnf3
_database_code_depnum_ccdc_archive 'CCDC 265209'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N O4'
_chemical_formula_weight         261.27

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'
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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n '

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

_cell_length_a                   6.9505(8)
_cell_length_b                   28.848(3)
_cell_length_c                   7.3706(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.961(2)
_cell_angle_gamma                90.00
_cell_volume                     1317.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2258
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.48
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_max          0.45
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6862
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2321
_reflns_number_gt                1886
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0464P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0010(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2321
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.5198(2) 0.09902(5) 0.8654(2) 0.0296(4) Uani 1 1 d . . .
H1 H 0.5437 0.1037 0.7427 0.036 Uiso 1 1 calc R . .
C2 C 0.7294(2) 0.08625(5) 1.0422(2) 0.0328(4) Uani 1 1 d . . .
H2 H 0.7302 0.0866 1.1782 0.039 Uiso 1 1 calc R . .
C3 C 0.8617(3) 0.04890(6) 1.0115(3) 0.0455(5) Uani 1 1 d . . .
H3A H 0.9369 0.0267 1.1242 0.055 Uiso 1 1 calc R . .
H3B H 0.8085 0.0356 0.8733 0.055 Uiso 1 1 calc R . .
C4 C 0.9404(3) 0.09792(6) 1.0428(3) 0.0452(5) Uani 1 1 d . . .
H4A H 0.9356 0.1148 0.9240 0.054 Uiso 1 1 calc R . .
H4B H 1.0640 0.1059 1.1749 0.054 Uiso 1 1 calc R . .
C5 C 0.3452(3) 0.06370(5) 0.8173(3) 0.0371(4) Uani 1 1 d . . .
H5 H 0.3277 0.0515 0.9360 0.045 Uiso 1 1 calc R . .
C6 C 0.3029(3) 0.02978(7) 0.6492(3) 0.0556(5) Uani 1 1 d . . .
H6A H 0.3902 0.0326 0.5745 0.067 Uiso 1 1 calc R . .
H6B H 0.2641 -0.0023 0.6667 0.067 Uiso 1 1 calc R . .
C7 C 0.1430(3) 0.06731(7) 0.6207(3) 0.0539(5) Uani 1 1 d . . .
H7A H 0.1315 0.0932 0.5284 0.065 Uiso 1 1 calc R . .
H7B H 0.0054 0.0583 0.6205 0.065 Uiso 1 1 calc R . .
C8 C 0.5072(2) 0.18247(5) 0.8728(2) 0.0257(4) Uani 1 1 d . . .
C9 C 0.3794(2) 0.22269(5) 0.88724(19) 0.0243(3) Uani 1 1 d . . .
C10 C 0.1929(2) 0.21705(5) 0.9115(2) 0.0264(4) Uani 1 1 d . . .
H10 H 0.1454 0.1868 0.9230 0.032 Uiso 1 1 calc R . .
C11 C 0.0769(2) 0.25542(5) 0.9190(2) 0.0280(4) Uani 1 1 d . . .
H11 H -0.0512 0.2519 0.9337 0.034 Uiso 1 1 calc R . .
C12 C 0.1520(2) 0.29884(5) 0.9044(2) 0.0251(3) Uani 1 1 d . . .
C13 C 0.3362(2) 0.30565(5) 0.8809(2) 0.0277(4) Uani 1 1 d . . .
H13 H 0.3840 0.3360 0.8719 0.033 Uiso 1 1 calc R . .
C14 C 0.4490(2) 0.26712(5) 0.8709(2) 0.0273(4) Uani 1 1 d . . .
H14 H 0.5750 0.2709 0.8526 0.033 Uiso 1 1 calc R . .
N1 N 0.0287(2) 0.33975(5) 0.91144(18) 0.0315(3) Uani 1 1 d . . .
O1 O 0.43325(15) 0.14225(3) 0.90706(16) 0.0307(3) Uani 1 1 d . . .
O2 O 0.65645(16) 0.18626(3) 0.83178(16) 0.0321(3) Uani 1 1 d . . .
O3 O 0.11526(18) 0.37795(4) 0.93646(18) 0.0423(3) Uani 1 1 d . . .
O4 O -0.15389(17) 0.33389(4) 0.89342(17) 0.0419(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 0.0380(9) 0.0219(8) 0.0351(9) -0.0009(7) 0.0219(7) 0.0007(7)
C2 0.0387(9) 0.0274(9) 0.0361(9) -0.0009(7) 0.0201(8) 0.0032(7)
C3 0.0474(10) 0.0351(10) 0.0581(12) -0.0017(8) 0.0277(9) 0.0077(8)
C4 0.0379(10) 0.0409(11) 0.0557(11) -0.0011(9) 0.0203(9) 0.0001(8)
C5 0.0426(9) 0.0296(9) 0.0413(9) -0.0006(7) 0.0208(8) -0.0067(7)
C6 0.0636(12) 0.0408(11) 0.0630(13) -0.0161(9) 0.0292(11) -0.0183(10)
C7 0.0441(11) 0.0548(13) 0.0554(12) -0.0041(10) 0.0161(10) -0.0122(9)
C8 0.0288(8) 0.0259(9) 0.0210(8) -0.0005(6) 0.0101(7) -0.0032(6)
C9 0.0257(8) 0.0264(8) 0.0177(7) 0.0005(6) 0.0071(6) 0.0000(6)
C10 0.0278(8) 0.0261(9) 0.0244(8) 0.0009(6) 0.0110(6) -0.0028(6)
C11 0.0254(8) 0.0316(9) 0.0268(8) 0.0018(7) 0.0118(7) -0.0001(6)
C12 0.0282(8) 0.0245(8) 0.0208(7) 0.0004(6) 0.0095(6) 0.0030(6)
C13 0.0320(8) 0.0225(8) 0.0282(8) 0.0008(6) 0.0132(7) -0.0029(6)
C14 0.0269(8) 0.0292(9) 0.0269(8) 0.0007(6) 0.0129(6) -0.0018(6)
N1 0.0370(8) 0.0318(8) 0.0268(7) 0.0025(6) 0.0154(6) 0.0028(6)
O1 0.0350(6) 0.0225(6) 0.0403(6) 0.0016(5) 0.0220(5) 0.0006(4)
O2 0.0366(6) 0.0282(6) 0.0393(7) -0.0011(5) 0.0241(5) -0.0013(5)
O3 0.0598(8) 0.0256(7) 0.0554(8) -0.0011(5) 0.0384(6) -0.0004(6)
O4 0.0308(6) 0.0425(8) 0.0524(8) 0.0002(6) 0.0188(6) 0.0068(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.
;

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 1.4762(17) . ?
C1 C2 1.495(2) . ?
C1 C5 1.499(2) . ?
C2 C3 1.499(2) . ?
C2 C4 1.503(2) . ?
C3 C4 1.496(2) . ?
C5 C7 1.496(2) . ?
C5 C6 1.500(2) . ?
C6 C7 1.497(3) . ?
C8 O2 1.2097(17) . ?
C8 O1 1.3386(16) . ?
C8 C9 1.494(2) . ?
C9 C14 1.3946(19) . ?
C9 C10 1.3959(19) . ?
C10 C11 1.385(2) . ?
C11 C12 1.380(2) . ?
C12 C13 1.381(2) . ?
C12 N1 1.4734(19) . ?
C13 C14 1.382(2) . ?
N1 O4 1.2261(16) . ?
N1 O3 1.2289(16) . ?

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 C2 110.79(12) . . ?
O1 C1 C5 105.12(11) . . ?
C2 C1 C5 113.77(13) . . ?
C1 C2 C3 117.90(13) . . ?
C1 C2 C4 120.76(14) . . ?
C3 C2 C4 59.77(11) . . ?
C4 C3 C2 60.24(11) . . ?
C3 C4 C2 59.98(11) . . ?
C7 C5 C1 119.09(15) . . ?
C7 C5 C6 59.96(12) . . ?
C1 C5 C6 118.25(14) . . ?
C7 C6 C5 59.90(11) . . ?
C5 C7 C6 60.14(11) . . ?
O2 C8 O1 124.86(13) . . ?
O2 C8 C9 123.55(13) . . ?
O1 C8 C9 111.58(12) . . ?
C14 C9 C10 119.82(13) . . ?
C14 C9 C8 117.79(13) . . ?
C10 C9 C8 122.37(13) . . ?
C11 C10 C9 120.19(14) . . ?
C12 C11 C10 118.35(13) . . ?
C11 C12 C13 122.94(14) . . ?
C11 C12 N1 118.52(13) . . ?
C13 C12 N1 118.53(13) . . ?
C12 C13 C14 118.24(14) . . ?
C13 C14 C9 120.45(13) . . ?
O4 N1 O3 123.51(13) . . ?
O4 N1 C12 118.43(13) . . ?
O3 N1 C12 118.05(12) . . ?
C8 O1 C1 117.73(11) . . ?

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
O1 C1 C2 C3 -168.08(13) . . . . ?
C5 C1 C2 C3 73.75(18) . . . . ?
O1 C1 C2 C4 -98.43(16) . . . . ?
C5 C1 C2 C4 143.40(15) . . . . ?
C1 C2 C3 C4 111.18(16) . . . . ?
C1 C2 C4 C3 -106.46(16) . . . . ?
O1 C1 C5 C7 70.85(18) . . . . ?
C2 C1 C5 C7 -167.77(15) . . . . ?
O1 C1 C5 C6 140.28(14) . . . . ?
C2 C1 C5 C6 -98.35(18) . . . . ?
C1 C5 C6 C7 -109.07(17) . . . . ?
C1 C5 C7 C6 107.69(17) . . . . ?
O2 C8 C9 C14 -6.1(2) . . . . ?
O1 C8 C9 C14 175.04(12) . . . . ?
O2 C8 C9 C10 172.44(13) . . . . ?
O1 C8 C9 C10 -6.45(18) . . . . ?
C14 C9 C10 C11 0.1(2) . . . . ?
C8 C9 C10 C11 -178.35(12) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C10 C11 C12 N1 179.77(12) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
N1 C12 C13 C14 -178.89(12) . . . . ?
C12 C13 C14 C9 -1.0(2) . . . . ?
C10 C9 C14 C13 0.8(2) . . . . ?
C8 C9 C14 C13 179.33(12) . . . . ?
C11 C12 N1 O4 -12.80(19) . . . . ?
C13 C12 N1 O4 166.39(13) . . . . ?
C11 C12 N1 O3 166.73(13) . . . . ?
C13 C12 N1 O3 -14.07(19) . . . . ?
O2 C8 O1 C1 -8.6(2) . . . . ?
C9 C8 O1 C1 170.27(10) . . . . ?
C2 C1 O1 C8 83.57(15) . . . . ?
C5 C1 O1 C8 -153.12(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037

data_jmwnf16
_database_code_depnum_ccdc_archive 'CCDC 265210'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N2 O5 S'
_chemical_formula_weight         270.26

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   5.1517(14)
_cell_length_b                   11.726(3)
_cell_length_c                   18.705(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.289(5)
_cell_angle_gamma                90.00
_cell_volume                     1126.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1017
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      23.93
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5769
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1981
_reflns_number_gt                1502
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0352P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0003(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1981
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
S1 S 0.78435(16) 0.99794(6) 0.91125(4) 0.0284(3) Uani 1 1 d . . .
O2 O 0.9972(4) 0.82104(18) 0.96103(12) 0.0361(6) Uani 1 1 d . . .
O3 O 0.9605(4) 0.64316(18) 0.93008(11) 0.0341(6) Uani 1 1 d . . .
N1 N 0.8865(5) 0.7422(2) 0.92679(13) 0.0262(6) Uani 1 1 d . . .
O5 O 0.2122(4) 0.52363(17) 0.78018(11) 0.0345(6) Uani 1 1 d . . .
O4 O -0.0674(4) 0.64904(18) 0.73891(12) 0.0364(6) Uani 1 1 d . . .
N2 N 0.1365(5) 0.6223(2) 0.77158(13) 0.0266(7) Uani 1 1 d . . .
C8 C 0.3020(6) 0.7132(2) 0.80400(15) 0.0219(7) Uani 1 1 d . . .
C7 C 0.5146(6) 0.6856(2) 0.84803(14) 0.0206(7) Uani 1 1 d . . .
H10 H 0.5609 0.6098 0.8560 0.025 Uiso 1 1 calc R . .
O1 O 0.6478(4) 1.11009(16) 0.87189(11) 0.0295(6) Uani 1 1 d . . .
C5 C 0.5963(6) 0.8890(2) 0.87007(16) 0.0233(7) Uani 1 1 d . . .
C10 C 0.3792(6) 0.9127(2) 0.82351(15) 0.0235(7) Uani 1 1 d . . .
H6 H 0.3336 0.9883 0.8141 0.028 Uiso 1 1 calc R . .
C9 C 0.2309(6) 0.8274(2) 0.79116(15) 0.0242(7) Uani 1 1 d . . .
H5 H 0.0846 0.8450 0.7610 0.029 Uiso 1 1 calc R . .
C6 C 0.6610(6) 0.7727(2) 0.88073(15) 0.0206(7) Uani 1 1 d . . .
C1 C 0.4759(6) 1.1752(2) 0.91568(17) 0.0295(8) Uani 1 1 d . . .
H1A H 0.5507 1.1800 0.9647 0.035 Uiso 1 1 calc R . .
H1B H 0.3076 1.1381 0.9157 0.035 Uiso 1 1 calc R . .
C2 C 0.4465(6) 1.2907(3) 0.88417(17) 0.0300(8) Uani 1 1 d . . .
H2A H 0.3369 1.2959 0.8392 0.036 Uiso 1 1 calc R . .
C4 C 0.6675(7) 1.3717(3) 0.89204(17) 0.0337(9) Uani 1 1 d . . .
H4A H 0.6930 1.4225 0.8522 0.040 Uiso 1 1 calc R . .
H4B H 0.8265 1.3461 0.9182 0.040 Uiso 1 1 calc R . .
C3 C 0.4367(7) 1.3914(3) 0.93340(18) 0.0346(9) Uani 1 1 d . . .
H3A H 0.3213 1.4538 0.9186 0.042 Uiso 1 1 calc R . .
H3B H 0.4549 1.3773 0.9846 0.042 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
S1 0.0339(5) 0.0159(4) 0.0349(5) -0.0028(4) 0.0002(4) -0.0022(3)
O2 0.0398(15) 0.0259(14) 0.0406(14) -0.0044(11) -0.0100(11) -0.0034(11)
O3 0.0388(15) 0.0197(13) 0.0429(14) 0.0065(10) -0.0028(11) 0.0080(11)
N1 0.0307(16) 0.0207(15) 0.0270(15) 0.0016(12) 0.0001(13) 0.0018(12)
O5 0.0484(16) 0.0136(12) 0.0404(14) -0.0029(10) -0.0045(12) -0.0014(10)
O4 0.0303(14) 0.0349(14) 0.0425(14) -0.0081(11) -0.0077(12) -0.0014(11)
N2 0.0313(17) 0.0242(16) 0.0245(14) -0.0032(12) 0.0038(13) -0.0030(13)
C8 0.0273(18) 0.0179(17) 0.0207(16) -0.0035(13) 0.0034(14) -0.0015(13)
C7 0.0303(18) 0.0117(15) 0.0207(15) -0.0004(13) 0.0086(14) 0.0024(13)
O1 0.0427(14) 0.0136(11) 0.0330(12) 0.0014(9) 0.0085(11) 0.0003(10)
C5 0.0259(18) 0.0196(16) 0.0253(16) 0.0024(13) 0.0069(14) -0.0004(13)
C10 0.0303(19) 0.0136(15) 0.0272(17) 0.0034(14) 0.0057(14) 0.0023(14)
C9 0.0277(19) 0.0225(18) 0.0224(16) 0.0027(13) 0.0015(14) 0.0034(14)
C6 0.0221(17) 0.0192(16) 0.0208(16) 0.0005(13) 0.0048(13) 0.0021(13)
C1 0.032(2) 0.0216(18) 0.0351(19) -0.0040(15) 0.0047(16) -0.0029(14)
C2 0.037(2) 0.0233(18) 0.0287(18) -0.0032(14) -0.0053(15) 0.0050(15)
C4 0.041(2) 0.0236(18) 0.037(2) 0.0005(15) 0.0083(17) 0.0016(15)
C3 0.048(2) 0.0210(18) 0.0359(19) -0.0029(15) 0.0082(17) -0.0005(16)

_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
S1 O1 1.640(2) . ?
S1 C5 1.747(3) . ?
O2 N1 1.239(3) . ?
O3 N1 1.223(3) . ?
N1 C6 1.439(4) . ?
O5 N2 1.227(3) . ?
O4 N2 1.216(3) . ?
N2 C8 1.467(4) . ?
C8 C7 1.359(4) . ?
C8 C9 1.404(4) . ?
C7 C6 1.385(4) . ?
C7 H10 0.9300 . ?
O1 C1 1.465(3) . ?
C5 C10 1.393(4) . ?
C5 C6 1.415(4) . ?
C10 C9 1.372(4) . ?
C10 H6 0.9300 . ?
C9 H5 0.9300 . ?
C1 C2 1.480(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.482(4) . ?
C2 C3 1.501(4) . ?
C2 H2A 0.9800 . ?
C4 C3 1.484(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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 S1 C5 100.55(13) . . ?
O3 N1 O2 123.6(3) . . ?
O3 N1 C6 120.1(3) . . ?
O2 N1 C6 116.4(2) . . ?
O4 N2 O5 124.2(3) . . ?
O4 N2 C8 118.3(3) . . ?
O5 N2 C8 117.5(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 N2 119.6(3) . . ?
C9 C8 N2 119.1(3) . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H10 120.7 . . ?
C6 C7 H10 120.7 . . ?
C1 O1 S1 115.08(18) . . ?
C10 C5 C6 116.8(3) . . ?
C10 C5 S1 121.5(2) . . ?
C6 C5 S1 121.7(2) . . ?
C9 C10 C5 121.6(3) . . ?
C9 C10 H6 119.2 . . ?
C5 C10 H6 119.2 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H5 120.3 . . ?
C8 C9 H5 120.3 . . ?
C7 C6 C5 122.3(3) . . ?
C7 C6 N1 118.0(3) . . ?
C5 C6 N1 119.7(3) . . ?
O1 C1 C2 107.6(2) . . ?
O1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C1 C2 C4 119.5(3) . . ?
C1 C2 C3 118.9(3) . . ?
C4 C2 C3 59.7(2) . . ?
C1 C2 H2A 115.7 . . ?
C4 C2 H2A 115.7 . . ?
C3 C2 H2A 115.7 . . ?
C2 C4 C3 60.8(2) . . ?
C2 C4 H4A 117.7 . . ?
C3 C4 H4A 117.7 . . ?
C2 C4 H4B 117.7 . . ?
C3 C4 H4B 117.7 . . ?
H4A C4 H4B 114.8 . . ?
C4 C3 C2 59.5(2) . . ?
C4 C3 H3A 117.8 . . ?
C2 C3 H3A 117.8 . . ?
C4 C3 H3B 117.8 . . ?
C2 C3 H3B 117.8 . . ?
H3A C3 H3B 115.0 . . ?

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
O4 N2 C8 C7 172.0(3) . . . . ?
O5 N2 C8 C7 -7.0(4) . . . . ?
O4 N2 C8 C9 -5.4(4) . . . . ?
O5 N2 C8 C9 175.6(3) . . . . ?
C9 C8 C7 C6 0.4(4) . . . . ?
N2 C8 C7 C6 -177.0(2) . . . . ?
C5 S1 O1 C1 103.7(2) . . . . ?
O1 S1 C5 C10 -5.8(3) . . . . ?
O1 S1 C5 C6 172.4(2) . . . . ?
C6 C5 C10 C9 1.8(4) . . . . ?
S1 C5 C10 C9 -179.9(2) . . . . ?
C5 C10 C9 C8 -1.3(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
N2 C8 C9 C10 177.5(3) . . . . ?
C8 C7 C6 C5 0.2(4) . . . . ?
C8 C7 C6 N1 -179.6(2) . . . . ?
C10 C5 C6 C7 -1.3(4) . . . . ?
S1 C5 C6 C7 -179.6(2) . . . . ?
C10 C5 C6 N1 178.5(2) . . . . ?
S1 C5 C6 N1 0.3(4) . . . . ?
O3 N1 C6 C7 8.0(4) . . . . ?
O2 N1 C6 C7 -172.7(3) . . . . ?
O3 N1 C6 C5 -171.9(3) . . . . ?
O2 N1 C6 C5 7.5(4) . . . . ?
S1 O1 C1 C2 160.2(2) . . . . ?
O1 C1 C2 C4 -72.4(3) . . . . ?
O1 C1 C2 C3 -141.9(3) . . . . ?
C1 C2 C4 C3 -108.2(3) . . . . ?
C1 C2 C3 C4 109.2(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         0.267
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.065

data_jmwnf18
_database_code_depnum_ccdc_archive 'CCDC 265211'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 N2 O6'
_chemical_formula_weight         266.21

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'
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   'Pna2(1) '

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'

_cell_length_a                   10.1620(8)
_cell_length_b                   21.4665(17)
_cell_length_c                   5.4350(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1185.60(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3397
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.37
_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.12
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_max          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multiscan
_exptl_absorpt_correction_T_min  0.9
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'Bruker SAINT'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7145
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2625
_reflns_number_gt                2532
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0548P)^2^+0.0122P] 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     SHELXL
_refine_ls_extinction_coef       0.0001(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(9)
_refine_ls_number_reflns         2625
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.93715(19) 0.28100(7) 0.1436(4) 0.0294(4) Uani 1 1 d . . .
H1A H 1.0291 0.2888 0.1071 0.035 Uiso 1 1 calc R . .
H1B H 0.8917 0.2725 -0.0097 0.035 Uiso 1 1 calc R . .
C2 C 0.92473(17) 0.22664(7) 0.3128(4) 0.0293(4) Uani 1 1 d . . .
H2 H 0.8352 0.2118 0.3456 0.035 Uiso 1 1 calc R . .
C3 C 1.03008(19) 0.17760(8) 0.2958(4) 0.0322(4) Uani 1 1 d . . .
H3A H 1.0038 0.1344 0.3151 0.039 Uiso 1 1 calc R . .
H3B H 1.1016 0.1845 0.1809 0.039 Uiso 1 1 calc R . .
C4 C 1.0222(2) 0.21890(8) 0.5162(4) 0.0351(4) Uani 1 1 d . . .
H4A H 1.0893 0.2507 0.5350 0.042 Uiso 1 1 calc R . .
H4B H 0.9915 0.2007 0.6691 0.042 Uiso 1 1 calc R . .
C5 C 0.89516(15) 0.38903(7) 0.1450(3) 0.0204(3) Uani 1 1 d . . .
C6 C 0.83562(15) 0.44289(7) 0.2806(3) 0.0192(3) Uani 1 1 d . . .
C7 C 0.85422(15) 0.50208(7) 0.1826(3) 0.0190(3) Uani 1 1 d . . .
H7 H 0.9052 0.5078 0.0423 0.023 Uiso 1 1 calc R . .
C8 C 0.79524(15) 0.55244(7) 0.2983(3) 0.0198(3) Uani 1 1 d . . .
C9 C 0.71908(15) 0.54647(7) 0.5065(3) 0.0187(3) Uani 1 1 d . . .
H9 H 0.6808 0.5808 0.5824 0.022 Uiso 1 1 calc R . .
C10 C 0.70241(15) 0.48659(7) 0.5970(3) 0.0185(3) Uani 1 1 d . . .
C11 C 0.75905(15) 0.43452(7) 0.4907(3) 0.0191(3) Uani 1 1 d . . .
H11 H 0.7464 0.3951 0.5575 0.023 Uiso 1 1 calc R . .
N1 N 0.80808(14) 0.61478(6) 0.1858(3) 0.0233(3) Uani 1 1 d . . .
N2 N 0.61706(13) 0.47803(6) 0.8132(2) 0.0203(3) Uani 1 1 d . . .
O1 O 0.87913(12) 0.33552(5) 0.2636(2) 0.0250(3) Uani 1 1 d . . .
O2 O 0.94919(12) 0.39482(5) -0.0520(2) 0.0287(3) Uani 1 1 d . . .
O3 O 0.85677(13) 0.61790(5) -0.0199(2) 0.0306(3) Uani 1 1 d . . .
O4 O 0.76687(13) 0.65935(5) 0.3022(2) 0.0324(3) Uani 1 1 d . . .
O5 O 0.58968(12) 0.42486(5) 0.8757(3) 0.0300(3) Uani 1 1 d . . .
O6 O 0.57882(12) 0.52496(5) 0.9209(2) 0.0252(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 0.0335(10) 0.0203(9) 0.0344(11) -0.0053(8) 0.0079(8) 0.0048(6)
C2 0.0259(9) 0.0195(8) 0.0425(11) -0.0055(8) 0.0051(8) -0.0003(6)
C3 0.0320(9) 0.0216(8) 0.0431(12) -0.0071(9) -0.0024(9) 0.0032(7)
C4 0.0462(12) 0.0230(9) 0.0362(10) -0.0054(8) 0.0001(9) -0.0017(8)
C5 0.0158(7) 0.0222(8) 0.0233(8) -0.0015(7) 0.0011(7) -0.0005(6)
C6 0.0161(7) 0.0195(8) 0.0220(8) -0.0008(6) -0.0032(7) -0.0009(6)
C7 0.0158(7) 0.0226(8) 0.0186(7) 0.0021(7) -0.0002(6) -0.0018(6)
C8 0.0172(7) 0.0190(8) 0.0232(8) 0.0038(7) -0.0047(7) -0.0020(5)
C9 0.0159(7) 0.0196(8) 0.0206(7) -0.0018(7) -0.0023(6) 0.0008(5)
C10 0.0159(8) 0.0229(8) 0.0166(7) 0.0007(7) -0.0020(6) -0.0015(6)
C11 0.0183(7) 0.0187(7) 0.0204(7) 0.0018(6) -0.0018(7) -0.0017(6)
N1 0.0213(7) 0.0206(7) 0.0278(8) 0.0062(6) -0.0037(6) -0.0019(5)
N2 0.0185(7) 0.0253(7) 0.0170(7) 0.0020(6) -0.0009(6) -0.0001(5)
O1 0.0280(6) 0.0188(6) 0.0281(6) -0.0005(5) 0.0064(5) 0.0026(4)
O2 0.0308(6) 0.0274(6) 0.0278(7) -0.0002(5) 0.0072(6) 0.0018(5)
O3 0.0364(7) 0.0285(6) 0.0270(6) 0.0088(6) 0.0028(6) -0.0040(5)
O4 0.0370(7) 0.0192(6) 0.0408(8) 0.0035(6) 0.0050(6) 0.0056(5)
O5 0.0348(7) 0.0253(6) 0.0300(7) 0.0067(5) 0.0094(6) -0.0015(5)
O6 0.0231(6) 0.0289(6) 0.0236(6) -0.0040(5) 0.0026(5) 0.0019(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 1.4640(19) . ?
C1 C2 1.491(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.494(3) . ?
C2 C3 1.504(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.492(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O2 1.209(2) . ?
C5 O1 1.3274(19) . ?
C5 C6 1.499(2) . ?
C6 C7 1.390(2) . ?
C6 C11 1.393(2) . ?
C7 C8 1.387(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(2) . ?
C8 N1 1.477(2) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(2) . ?
C10 N2 1.472(2) . ?
C11 H11 0.9300 . ?
N1 O4 1.2210(18) . ?
N1 O3 1.2245(19) . ?
N2 O5 1.2228(17) . ?
N2 O6 1.2282(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 C2 108.46(15) . . ?
O1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C1 C2 C4 119.16(15) . . ?
C1 C2 C3 116.72(16) . . ?
C4 C2 C3 59.71(12) . . ?
C1 C2 H2 116.4 . . ?
C4 C2 H2 116.4 . . ?
C3 C2 H2 116.4 . . ?
C4 C3 C2 59.80(13) . . ?
C4 C3 H3A 117.8 . . ?
C2 C3 H3A 117.8 . . ?
C4 C3 H3B 117.8 . . ?
C2 C3 H3B 117.8 . . ?
H3A C3 H3B 114.9 . . ?
C3 C4 C2 60.49(13) . . ?
C3 C4 H4A 117.7 . . ?
C2 C4 H4A 117.7 . . ?
C3 C4 H4B 117.7 . . ?
C2 C4 H4B 117.7 . . ?
H4A C4 H4B 114.8 . . ?
O2 C5 O1 125.08(15) . . ?
O2 C5 C6 122.63(15) . . ?
O1 C5 C6 112.28(14) . . ?
C7 C6 C11 120.49(15) . . ?
C7 C6 C5 117.50(15) . . ?
C11 C6 C5 121.94(14) . . ?
C8 C7 C6 118.69(15) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C9 C8 C7 122.88(14) . . ?
C9 C8 N1 118.29(14) . . ?
C7 C8 N1 118.73(15) . . ?
C8 C9 C10 116.52(14) . . ?
C8 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
C11 C10 C9 123.34(15) . . ?
C11 C10 N2 118.53(14) . . ?
C9 C10 N2 118.10(13) . . ?
C10 C11 C6 118.07(15) . . ?
C10 C11 H11 121.0 . . ?
C6 C11 H11 121.0 . . ?
O4 N1 O3 124.66(14) . . ?
O4 N1 C8 117.74(14) . . ?
O3 N1 C8 117.58(14) . . ?
O5 N2 O6 124.13(14) . . ?
O5 N2 C10 118.20(13) . . ?
O6 N2 C10 117.67(12) . . ?
C5 O1 C1 115.21(13) . . ?

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
O1 C1 C2 C4 -81.1(2) . . . . ?
O1 C1 C2 C3 -149.64(16) . . . . ?
C1 C2 C3 C4 109.74(18) . . . . ?
C1 C2 C4 C3 -105.68(19) . . . . ?
O2 C5 C6 C7 -5.6(2) . . . . ?
O1 C5 C6 C7 175.61(14) . . . . ?
O2 C5 C6 C11 171.49(16) . . . . ?
O1 C5 C6 C11 -7.4(2) . . . . ?
C11 C6 C7 C8 0.1(2) . . . . ?
C5 C6 C7 C8 177.15(14) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C6 C7 C8 N1 -176.26(13) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
N1 C8 C9 C10 175.87(14) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C8 C9 C10 N2 -177.46(13) . . . . ?
C9 C10 C11 C6 -0.6(2) . . . . ?
N2 C10 C11 C6 177.60(13) . . . . ?
C7 C6 C11 C10 0.2(2) . . . . ?
C5 C6 C11 C10 -176.77(14) . . . . ?
C9 C8 N1 O4 10.5(2) . . . . ?
C7 C8 N1 O4 -172.91(15) . . . . ?
C9 C8 N1 O3 -167.91(14) . . . . ?
C7 C8 N1 O3 8.6(2) . . . . ?
C11 C10 N2 O5 -6.8(2) . . . . ?
C9 C10 N2 O5 171.50(14) . . . . ?
C11 C10 N2 O6 172.50(15) . . . . ?
C9 C10 N2 O6 -9.2(2) . . . . ?
O2 C5 O1 C1 2.3(2) . . . . ?
C6 C5 O1 C1 -178.91(14) . . . . ?
C2 C1 O1 C5 173.33(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043

data_jmwnf23
_database_code_depnum_ccdc_archive 'CCDC 265212'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 N O4'
_chemical_formula_weight         221.21

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'
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           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                   11.503(2)
_cell_length_b                   7.7574(16)
_cell_length_c                   12.737(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.040(4)
_cell_angle_gamma                90.00
_cell_volume                     1060.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1037
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      25.08
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_max          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4383
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1833
_reflns_number_gt                1267
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0345P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0002(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1833
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_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 0.5526(2) 0.7370(3) 0.4411(2) 0.0406(6) Uani 1 1 d . . .
H1A H 0.5840 0.8409 0.4182 0.049 Uiso 1 1 calc R . .
H1B H 0.5273 0.7653 0.5040 0.049 Uiso 1 1 calc R . .
C2 C 0.44409(19) 0.6703(3) 0.34599(19) 0.0324(6) Uani 1 1 d . . .
H2 H 0.4066 0.5637 0.3603 0.039 Uiso 1 1 calc R . .
C3 C 0.3559(2) 0.7994(3) 0.2712(2) 0.0437(7) Uani 1 1 d . . .
H3A H 0.2678 0.7717 0.2430 0.052 Uiso 1 1 calc R . .
H3B H 0.3751 0.9207 0.2868 0.052 Uiso 1 1 calc R . .
C4 C 0.4388(2) 0.6965(3) 0.2283(2) 0.0431(6) Uani 1 1 d . . .
H4A H 0.5081 0.7553 0.2177 0.052 Uiso 1 1 calc R . .
H4B H 0.4009 0.6064 0.1740 0.052 Uiso 1 1 calc R . .
C5 C 0.76580(19) 0.6606(3) 0.53222(17) 0.0279(5) Uani 1 1 d . . .
C6 C 0.85695(19) 0.5158(2) 0.56864(16) 0.0252(5) Uani 1 1 d . . .
C7 C 0.98208(18) 0.5580(3) 0.62787(16) 0.0264(5) Uani 1 1 d . . .
H7 H 1.0052 0.6726 0.6443 0.032 Uiso 1 1 calc R . .
C8 C 1.07125(19) 0.4293(3) 0.66193(16) 0.0276(5) Uani 1 1 d . . .
H8 H 1.1543 0.4562 0.7016 0.033 Uiso 1 1 calc R . .
C9 C 1.03461(18) 0.2604(2) 0.63591(16) 0.0249(5) Uani 1 1 d . . .
C10 C 0.91133(19) 0.2140(3) 0.57933(16) 0.0281(5) Uani 1 1 d . . .
H10 H 0.8889 0.0989 0.5644 0.034 Uiso 1 1 calc R . .
C11 C 0.82279(19) 0.3428(2) 0.54573(17) 0.0269(5) Uani 1 1 d . . .
H11 H 0.7397 0.3143 0.5075 0.032 Uiso 1 1 calc R . .
N1 N 1.13093(17) 0.1238(2) 0.66939(14) 0.0314(5) Uani 1 1 d . . .
O1 O 0.64979(13) 0.60577(17) 0.47489(12) 0.0338(4) Uani 1 1 d . . .
O2 O 0.79309(14) 0.81055(19) 0.55219(14) 0.0435(5) Uani 1 1 d . . .
O3 O 1.09806(13) -0.02690(18) 0.64763(12) 0.0392(4) Uani 1 1 d . . .
O4 O 1.24012(14) 0.16803(19) 0.71821(14) 0.0449(5) 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 0.0355(14) 0.0341(13) 0.0472(15) 0.0022(11) 0.0087(12) 0.0106(11)
C2 0.0214(12) 0.0293(12) 0.0449(15) 0.0045(11) 0.0101(11) 0.0017(10)
C3 0.0240(13) 0.0321(13) 0.0641(18) 0.0057(12) 0.0024(12) 0.0034(11)
C4 0.0357(14) 0.0464(15) 0.0426(15) 0.0016(12) 0.0083(12) -0.0019(12)
C5 0.0289(13) 0.0311(13) 0.0229(12) -0.0019(10) 0.0085(10) -0.0055(10)
C6 0.0252(12) 0.0314(12) 0.0199(11) 0.0014(10) 0.0091(9) -0.0010(10)
C7 0.0269(13) 0.0284(12) 0.0239(12) -0.0031(9) 0.0093(10) -0.0067(10)
C8 0.0191(11) 0.0371(13) 0.0255(12) -0.0019(10) 0.0069(10) -0.0062(10)
C9 0.0231(12) 0.0306(12) 0.0224(12) 0.0031(10) 0.0098(10) 0.0006(10)
C10 0.0312(13) 0.0279(12) 0.0265(13) -0.0029(10) 0.0119(11) -0.0049(10)
C11 0.0211(12) 0.0320(12) 0.0268(13) 0.0002(10) 0.0078(10) -0.0050(9)
N1 0.0320(12) 0.0367(11) 0.0289(11) 0.0012(9) 0.0151(9) -0.0003(9)
O1 0.0248(9) 0.0293(8) 0.0416(9) 0.0005(7) 0.0051(8) 0.0017(7)
O2 0.0355(10) 0.0295(9) 0.0580(11) -0.0038(8) 0.0076(8) -0.0023(7)
O3 0.0415(10) 0.0300(9) 0.0468(10) 0.0014(8) 0.0166(8) 0.0021(8)
O4 0.0193(9) 0.0520(10) 0.0569(11) -0.0037(9) 0.0057(8) 0.0000(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
C1 O1 1.458(2) . ?
C1 C2 1.485(3) . ?
C2 C4 1.491(3) . ?
C2 C3 1.498(3) . ?
C3 C4 1.490(3) . ?
C5 O2 1.208(2) . ?
C5 O1 1.340(2) . ?
C5 C6 1.493(3) . ?
C6 C11 1.399(3) . ?
C6 C7 1.403(3) . ?
C7 C8 1.385(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.388(3) . ?
C9 N1 1.481(3) . ?
C10 C11 1.380(3) . ?
N1 O3 1.229(2) . ?
N1 O4 1.233(2) . ?

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 C2 109.18(17) . . ?
C1 C2 C4 119.4(2) . . ?
C1 C2 C3 117.66(18) . . ?
C4 C2 C3 59.78(14) . . ?
C4 C3 C2 59.88(14) . . ?
C3 C4 C2 60.33(15) . . ?
O2 C5 O1 123.60(19) . . ?
O2 C5 C6 124.00(19) . . ?
O1 C5 C6 112.40(17) . . ?
C11 C6 C7 119.55(19) . . ?
C11 C6 C5 122.95(19) . . ?
C7 C6 C5 117.50(18) . . ?
C8 C7 C6 120.11(19) . . ?
C9 C8 C7 118.77(19) . . ?
C8 C9 C10 122.54(19) . . ?
C8 C9 N1 118.55(18) . . ?
C10 C9 N1 118.92(18) . . ?
C11 C10 C9 118.43(18) . . ?
C10 C11 C6 120.58(19) . . ?
O3 N1 O4 123.61(18) . . ?
O3 N1 C9 118.53(18) . . ?
O4 N1 C9 117.86(17) . . ?
C5 O1 C1 116.57(16) . . ?

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
O1 C1 C2 C4 -88.6(2) . . . . ?
O1 C1 C2 C3 -157.74(19) . . . . ?
C1 C2 C3 C4 109.7(2) . . . . ?
C1 C2 C4 C3 -106.8(2) . . . . ?
O2 C5 C6 C11 179.2(2) . . . . ?
O1 C5 C6 C11 -0.7(3) . . . . ?
O2 C5 C6 C7 -1.2(3) . . . . ?
O1 C5 C6 C7 178.94(16) . . . . ?
C11 C6 C7 C8 0.9(3) . . . . ?
C5 C6 C7 C8 -178.75(18) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C7 C8 C9 N1 178.11(17) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
N1 C9 C10 C11 -178.21(17) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C7 C6 C11 C10 -1.0(3) . . . . ?
C5 C6 C11 C10 178.63(18) . . . . ?
C8 C9 N1 O3 178.98(17) . . . . ?
C10 C9 N1 O3 -1.3(3) . . . . ?
C8 C9 N1 O4 -0.7(3) . . . . ?
C10 C9 N1 O4 179.02(17) . . . . ?
O2 C5 O1 C1 -3.2(3) . . . . ?
C6 C5 O1 C1 176.64(17) . . . . ?
C2 C1 O1 C5 159.02(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.041

data_jmwnf33
_database_code_depnum_ccdc_archive 'CCDC 265213'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N O3'
_chemical_formula_weight         193.20

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'
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           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                   11.1796(17)
_cell_length_b                   7.2234(11)
_cell_length_c                   12.745(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.033(3)
_cell_angle_gamma                90.00
_cell_volume                     932.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1180
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      26.83
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.01
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5551
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.59
_reflns_number_total             2115
_reflns_number_gt                1392
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0381P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2115
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_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 0.20084(14) 0.0880(2) 0.01934(14) 0.0252(4) Uani 1 1 d . . .
H1A H 0.1828 0.2095 0.0418 0.030 Uiso 1 1 calc R . .
H1B H 0.1799 -0.0043 0.0643 0.030 Uiso 1 1 calc R . .
C2 C 0.11880(15) 0.0575(2) -0.10647(15) 0.0260(4) Uani 1 1 d . . .
H2 H 0.1147 -0.0698 -0.1344 0.031 Uiso 1 1 calc R . .
C3 C -0.00558(15) 0.1700(2) -0.16242(15) 0.0305(5) Uani 1 1 d . . .
H3A H -0.0826 0.1104 -0.2211 0.037 Uiso 1 1 calc R . .
H3B H -0.0245 0.2595 -0.1148 0.037 Uiso 1 1 calc R . .
C4 C 0.10880(15) 0.2075(3) -0.19058(15) 0.0295(4) Uani 1 1 d . . .
H4A H 0.1589 0.3200 -0.1601 0.035 Uiso 1 1 calc R . .
H4B H 0.1010 0.1709 -0.2665 0.035 Uiso 1 1 calc R . .
C5 C 0.43072(14) 0.0874(2) 0.15279(14) 0.0222(4) Uani 1 1 d . . .
C6 C 0.40207(15) 0.1017(2) 0.24835(15) 0.0258(4) Uani 1 1 d . . .
H6 H 0.3148 0.1052 0.2384 0.031 Uiso 1 1 calc R . .
C7 C 0.50304(15) 0.1106(2) 0.35767(14) 0.0263(4) Uani 1 1 d . . .
H7 H 0.4844 0.1213 0.4219 0.032 Uiso 1 1 calc R . .
C8 C 0.63220(14) 0.1035(2) 0.37157(14) 0.0215(4) Uani 1 1 d . . .
C9 C 0.66215(15) 0.0919(2) 0.27691(15) 0.0266(4) Uani 1 1 d . . .
H9 H 0.7497 0.0899 0.2874 0.032 Uiso 1 1 calc R . .
C10 C 0.56201(15) 0.0831(2) 0.16772(14) 0.0273(4) Uani 1 1 d . . .
H10 H 0.5813 0.0744 0.1037 0.033 Uiso 1 1 calc R . .
N N 0.73790(12) 0.10773(19) 0.48756(12) 0.0252(3) Uani 1 1 d . . .
O1 O 0.33846(10) 0.07437(17) 0.04117(9) 0.0281(3) Uani 1 1 d . . .
O2 O 0.70928(11) 0.11917(18) 0.57072(10) 0.0347(3) Uani 1 1 d . . .
O3 O 0.85313(10) 0.09686(18) 0.49938(11) 0.0362(4) 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 0.0199(8) 0.0322(10) 0.0232(9) 0.0007(8) 0.0089(7) 0.0013(7)
C2 0.0247(9) 0.0254(10) 0.0244(9) -0.0030(7) 0.0069(7) -0.0011(7)
C3 0.0212(9) 0.0402(12) 0.0254(10) -0.0038(8) 0.0053(8) 0.0021(8)
C4 0.0291(9) 0.0361(11) 0.0227(9) -0.0014(8) 0.0104(8) -0.0016(8)
C5 0.0221(8) 0.0221(9) 0.0217(9) -0.0007(7) 0.0087(7) -0.0010(7)
C6 0.0203(8) 0.0337(10) 0.0256(9) 0.0019(8) 0.0118(7) 0.0027(8)
C7 0.0246(8) 0.0365(11) 0.0210(9) 0.0015(8) 0.0128(7) 0.0016(8)
C8 0.0222(8) 0.0184(9) 0.0208(9) 0.0012(7) 0.0062(7) 0.0004(7)
C9 0.0206(8) 0.0305(10) 0.0311(10) -0.0035(8) 0.0131(8) -0.0027(8)
C10 0.0269(9) 0.0369(11) 0.0220(9) -0.0033(8) 0.0143(8) -0.0022(8)
N 0.0239(7) 0.0243(8) 0.0250(8) 0.0012(6) 0.0080(6) -0.0008(6)
O1 0.0191(6) 0.0445(8) 0.0200(7) -0.0026(5) 0.0075(5) 0.0016(5)
O2 0.0328(7) 0.0503(9) 0.0202(7) -0.0008(6) 0.0105(6) 0.0021(6)
O3 0.0193(6) 0.0530(9) 0.0325(8) 0.0030(6) 0.0074(6) -0.0011(6)

_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 1.4464(17) . ?
C1 C2 1.489(2) . ?
C2 C4 1.495(2) . ?
C2 C3 1.504(2) . ?
C3 C4 1.492(2) . ?
C5 O1 1.3618(18) . ?
C5 C6 1.388(2) . ?
C5 C10 1.398(2) . ?
C6 C7 1.374(2) . ?
C7 C8 1.379(2) . ?
C8 C9 1.384(2) . ?
C8 N 1.451(2) . ?
C9 C10 1.369(2) . ?
N O2 1.2326(17) . ?
N O3 1.2345(16) . ?

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 C2 108.51(13) . . ?
C1 C2 C4 119.36(15) . . ?
C1 C2 C3 117.08(15) . . ?
C4 C2 C3 59.67(11) . . ?
C4 C3 C2 59.84(11) . . ?
C3 C4 C2 60.49(11) . . ?
O1 C5 C6 124.59(14) . . ?
O1 C5 C10 115.34(14) . . ?
C6 C5 C10 120.06(15) . . ?
C7 C6 C5 119.84(14) . . ?
C6 C7 C8 119.65(15) . . ?
C7 C8 C9 121.09(15) . . ?
C7 C8 N 119.15(15) . . ?
C9 C8 N 119.76(14) . . ?
C10 C9 C8 119.55(14) . . ?
C9 C10 C5 119.80(15) . . ?
O2 N O3 122.44(14) . . ?
O2 N C8 118.80(13) . . ?
O3 N C8 118.75(14) . . ?
C5 O1 C1 118.03(13) . . ?

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
O1 C1 C2 C4 -74.74(18) . . . . ?
O1 C1 C2 C3 -143.44(14) . . . . ?
C1 C2 C3 C4 109.81(17) . . . . ?
C1 C2 C4 C3 -106.02(17) . . . . ?
O1 C5 C6 C7 178.76(16) . . . . ?
C10 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 1.5(3) . . . . ?
C6 C7 C8 N -178.26(15) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
N C8 C9 C10 178.33(15) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
O1 C5 C10 C9 -178.76(15) . . . . ?
C6 C5 C10 C9 0.4(3) . . . . ?
C7 C8 N O2 -0.6(2) . . . . ?
C9 C8 N O2 179.61(15) . . . . ?
C7 C8 N O3 178.28(14) . . . . ?
C9 C8 N O3 -1.5(2) . . . . ?
C6 C5 O1 C1 4.1(2) . . . . ?
C10 C5 O1 C1 -176.72(14) . . . . ?
C2 C1 O1 C5 -176.28(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047

data_jmwf5a
_database_code_depnum_ccdc_archive 'CCDC 265214'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O6'
_chemical_formula_weight         306.27

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'
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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n '

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

_cell_length_a                   14.0459(19)
_cell_length_b                   7.8502(11)
_cell_length_c                   14.279(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.424(2)
_cell_angle_gamma                90.00
_cell_volume                     1422.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4933
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.14
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9945
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2498
_reflns_number_gt                2155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0505P)^2^+0.2699P] 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     SHELXL
_refine_ls_extinction_coef       0.0017(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2498
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.1012
_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 0.57516(14) 0.24270(18) 0.68230(12) 0.0332(4) Uani 1 1 d . . .
C2 C 0.47633(13) 0.1932(2) 0.59258(12) 0.0372(4) Uani 1 1 d . . .
C3 C 0.40973(16) 0.3299(2) 0.52034(16) 0.0483(5) Uani 1 1 d . . .
C4 C 0.37249(17) 0.2383(3) 0.59028(17) 0.0514(5) Uani 1 1 d . . .
C5 C 0.67406(15) 0.2429(2) 0.66614(13) 0.0405(4) Uani 1 1 d . . .
C6 C 0.66869(16) 0.2437(2) 0.55918(15) 0.0451(5) Uani 1 1 d . . .
C7 C 0.70552(15) 0.0875(2) 0.62523(15) 0.0438(4) Uani 1 1 d . . .
C8 C 0.56566(12) 0.15587(18) 0.84055(11) 0.0286(3) Uani 1 1 d . . .
C9 C 0.58256(11) 0.00743(17) 0.91218(11) 0.0267(3) Uani 1 1 d . . .
C10 C 0.55482(11) -0.16108(17) 0.87933(11) 0.0265(3) Uani 1 1 d . . .
C11 C 0.57980(12) -0.29657(18) 0.94715(11) 0.0275(3) Uani 1 1 d . . .
C12 C 0.63193(11) -0.25889(17) 1.05141(11) 0.0272(3) Uani 1 1 d . . .
C13 C 0.65925(12) -0.09508(18) 1.08850(12) 0.0297(3) Uani 1 1 d . . .
C14 C 0.63470(12) 0.03714(18) 1.01821(11) 0.0293(3) Uani 1 1 d . . .
N1 N 0.49130(11) -0.19789(15) 0.76885(10) 0.0358(3) Uani 1 1 d . . .
N2 N 0.65891(10) -0.39940(16) 1.12676(10) 0.0329(3) Uani 1 1 d . . .
O1 O 0.59367(9) 0.11491(12) 0.76573(8) 0.0341(3) Uani 1 1 d . . .
O2 O 0.53681(10) 0.29364(13) 0.85491(8) 0.0390(3) Uani 1 1 d . . .
O3 O 0.41493(10) -0.10745(15) 0.72215(9) 0.0462(3) Uani 1 1 d . . .
O4 O 0.51825(14) -0.31770(16) 0.73122(10) 0.0665(5) Uani 1 1 d . . .
O5 O 0.63811(10) -0.54516(13) 1.09350(9) 0.0452(3) Uani 1 1 d . . .
O6 O 0.69972(10) -0.36253(15) 1.21866(8) 0.0450(3) Uani 1 1 d . . .
H1 H 0.5705(13) 0.352(2) 0.7121(13) 0.034(4) Uiso 1 1 d . . .
H2 H 0.4805(15) 0.075(2) 0.5604(13) 0.048(5) Uiso 1 1 d . . .
H3A H 0.3781(14) 0.306(2) 0.4480(15) 0.037(4) Uiso 1 1 d . . .
H3B H 0.4335(16) 0.446(3) 0.5394(14) 0.051(5) Uiso 1 1 d . . .
H4A H 0.3148(16) 0.151(2) 0.5515(14) 0.046(5) Uiso 1 1 d . . .
H4B H 0.3770(16) 0.305(2) 0.6509(15) 0.051(5) Uiso 1 1 d . . .
H5 H 0.7357(18) 0.298(3) 0.7198(16) 0.058(6) Uiso 1 1 d . . .
H6A H 0.7213(18) 0.312(3) 0.5483(16) 0.060(6) Uiso 1 1 d . . .
H6B H 0.5935(19) 0.237(2) 0.4983(16) 0.057(6) Uiso 1 1 d . . .
H7A H 0.7820(18) 0.061(2) 0.6602(15) 0.062(6) Uiso 1 1 d . . .
H7B H 0.6540(17) -0.012(3) 0.6084(14) 0.057(5) Uiso 1 1 d . . .
H11 H 0.5610(12) -0.403(2) 0.9238(11) 0.025(4) Uiso 1 1 d . . .
H13 H 0.6940(13) -0.0768(19) 1.1616(13) 0.032(4) Uiso 1 1 d . . .
H14 H 0.6525(14) 0.147(2) 1.0400(12) 0.033(4) Uiso 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 0.0448(10) 0.0257(8) 0.0357(8) 0.0033(6) 0.0235(8) 0.0015(6)
C2 0.0422(10) 0.0349(8) 0.0401(9) 0.0033(7) 0.0229(8) 0.0000(7)
C3 0.0527(12) 0.0401(10) 0.0495(12) 0.0094(8) 0.0195(9) 0.0057(8)
C4 0.0441(11) 0.0616(12) 0.0514(11) 0.0092(10) 0.0233(9) 0.0126(9)
C5 0.0415(10) 0.0415(9) 0.0404(9) 0.0002(7) 0.0195(8) -0.0076(7)
C6 0.0441(11) 0.0518(11) 0.0509(11) 0.0156(8) 0.0312(10) 0.0070(8)
C7 0.0406(10) 0.0476(10) 0.0492(10) 0.0098(8) 0.0252(9) 0.0075(8)
C8 0.0285(8) 0.0279(7) 0.0317(8) -0.0037(6) 0.0150(7) -0.0031(6)
C9 0.0251(7) 0.0266(7) 0.0335(8) -0.0015(6) 0.0173(6) 0.0010(6)
C10 0.0262(8) 0.0278(7) 0.0283(7) -0.0030(6) 0.0143(6) -0.0005(6)
C11 0.0277(8) 0.0232(7) 0.0359(8) -0.0043(6) 0.0179(7) -0.0016(6)
C12 0.0256(8) 0.0284(7) 0.0324(8) 0.0021(6) 0.0169(6) 0.0023(5)
C13 0.0287(8) 0.0328(8) 0.0295(8) -0.0046(6) 0.0143(7) -0.0009(6)
C14 0.0309(8) 0.0247(7) 0.0352(8) -0.0069(6) 0.0170(7) -0.0040(6)
N1 0.0448(9) 0.0292(7) 0.0309(7) -0.0026(6) 0.0139(6) -0.0032(6)
N2 0.0317(7) 0.0336(7) 0.0366(8) 0.0041(5) 0.0179(6) 0.0054(5)
O1 0.0455(7) 0.0288(5) 0.0369(6) 0.0035(4) 0.0262(5) 0.0046(4)
O2 0.0555(8) 0.0270(6) 0.0409(6) 0.0003(4) 0.0268(6) 0.0056(5)
O3 0.0391(7) 0.0515(7) 0.0384(6) 0.0022(5) 0.0074(5) 0.0017(6)
O4 0.1011(12) 0.0471(8) 0.0367(7) -0.0128(6) 0.0158(7) 0.0206(7)
O5 0.0587(8) 0.0267(6) 0.0516(7) 0.0055(5) 0.0250(6) 0.0032(5)
O6 0.0527(8) 0.0480(7) 0.0314(6) 0.0080(5) 0.0153(6) 0.0110(6)

_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 C2 1.481(2) . ?
C1 O1 1.4924(17) . ?
C1 C5 1.503(2) . ?
C1 H1 0.974(17) . ?
C2 C4 1.488(3) . ?
C2 C3 1.504(2) . ?
C2 H2 1.046(18) . ?
C3 C4 1.495(3) . ?
C3 H3A 0.951(18) . ?
C3 H3B 0.97(2) . ?
C4 H4A 1.03(2) . ?
C4 H4B 0.99(2) . ?
C5 C6 1.497(2) . ?
C5 C7 1.498(2) . ?
C5 H5 0.98(2) . ?
C6 C7 1.497(2) . ?
C6 H6A 0.98(2) . ?
C6 H6B 1.04(2) . ?
C7 H7A 0.99(2) . ?
C7 H7B 1.02(2) . ?
C8 O2 1.2031(17) . ?
C8 O1 1.3268(17) . ?
C8 C9 1.501(2) . ?
C9 C14 1.390(2) . ?
C9 C10 1.402(2) . ?
C10 C11 1.379(2) . ?
C10 N1 1.4695(19) . ?
C11 C12 1.380(2) . ?
C11 H11 0.899(15) . ?
C12 C13 1.381(2) . ?
C12 N2 1.4724(18) . ?
C13 C14 1.381(2) . ?
C13 H13 0.955(17) . ?
C14 H14 0.912(17) . ?
N1 O3 1.2187(17) . ?
N1 O4 1.2213(18) . ?
N2 O6 1.2200(17) . ?
N2 O5 1.2252(16) . ?

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
C2 C1 O1 106.95(12) . . ?
C2 C1 C5 116.90(13) . . ?
O1 C1 C5 105.51(13) . . ?
C2 C1 H1 113.4(10) . . ?
O1 C1 H1 105.4(10) . . ?
C5 C1 H1 107.8(10) . . ?
C1 C2 C4 120.16(16) . . ?
C1 C2 C3 118.82(15) . . ?
C4 C2 C3 59.97(12) . . ?
C1 C2 H2 113.8(10) . . ?
C4 C2 H2 116.1(10) . . ?
C3 C2 H2 117.7(10) . . ?
C4 C3 C2 59.48(11) . . ?
C4 C3 H3A 119.8(11) . . ?
C2 C3 H3A 117.9(10) . . ?
C4 C3 H3B 116.1(11) . . ?
C2 C3 H3B 116.1(12) . . ?
H3A C3 H3B 115.7(16) . . ?
C2 C4 C3 60.56(12) . . ?
C2 C4 H4A 113.1(11) . . ?
C3 C4 H4A 112.5(10) . . ?
C2 C4 H4B 114.4(12) . . ?
C3 C4 H4B 114.7(11) . . ?
H4A C4 H4B 124.6(16) . . ?
C6 C5 C7 59.97(12) . . ?
C6 C5 C1 120.79(16) . . ?
C7 C5 C1 120.39(15) . . ?
C6 C5 H5 115.9(12) . . ?
C7 C5 H5 111.0(12) . . ?
C1 C5 H5 116.5(12) . . ?
C5 C6 C7 60.07(11) . . ?
C5 C6 H6A 117.0(12) . . ?
C7 C6 H6A 118.1(12) . . ?
C5 C6 H6B 116.1(11) . . ?
C7 C6 H6B 116.1(10) . . ?
H6A C6 H6B 117.2(16) . . ?
C6 C7 C5 59.96(11) . . ?
C6 C7 H7A 119.6(12) . . ?
C5 C7 H7A 114.2(12) . . ?
C6 C7 H7B 117.4(11) . . ?
C5 C7 H7B 114.6(12) . . ?
H7A C7 H7B 117.6(16) . . ?
O2 C8 O1 126.38(13) . . ?
O2 C8 C9 123.24(13) . . ?
O1 C8 C9 110.23(11) . . ?
C14 C9 C10 117.63(13) . . ?
C14 C9 C8 117.87(12) . . ?
C10 C9 C8 124.39(13) . . ?
C11 C10 C9 122.87(13) . . ?
C11 C10 N1 117.16(12) . . ?
C9 C10 N1 119.88(12) . . ?
C10 C11 C12 116.72(13) . . ?
C10 C11 H11 120.9(9) . . ?
C12 C11 H11 122.3(9) . . ?
C11 C12 C13 123.01(13) . . ?
C11 C12 N2 118.60(12) . . ?
C13 C12 N2 118.39(13) . . ?
C14 C13 C12 118.67(14) . . ?
C14 C13 H13 122.2(9) . . ?
C12 C13 H13 119.1(9) . . ?
C13 C14 C9 121.07(13) . . ?
C13 C14 H14 120.9(10) . . ?
C9 C14 H14 118.0(10) . . ?
O3 N1 O4 125.04(13) . . ?
O3 N1 C10 117.32(12) . . ?
O4 N1 C10 117.63(13) . . ?
O6 N2 O5 124.22(13) . . ?
O6 N2 C12 117.58(12) . . ?
O5 N2 C12 118.20(13) . . ?
C8 O1 C1 118.01(11) . . ?

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
O1 C1 C2 C4 80.58(17) . . . . ?
C5 C1 C2 C4 -161.52(15) . . . . ?
O1 C1 C2 C3 150.64(14) . . . . ?
C5 C1 C2 C3 -91.45(19) . . . . ?
C1 C2 C3 C4 -110.14(18) . . . . ?
C1 C2 C4 C3 107.94(18) . . . . ?
C2 C1 C5 C6 17.3(2) . . . . ?
O1 C1 C5 C6 136.03(15) . . . . ?
C2 C1 C5 C7 -53.6(2) . . . . ?
O1 C1 C5 C7 65.05(19) . . . . ?
C1 C5 C6 C7 -109.62(18) . . . . ?
C1 C5 C7 C6 110.27(19) . . . . ?
O2 C8 C9 C14 -43.7(2) . . . . ?
O1 C8 C9 C14 132.14(13) . . . . ?
O2 C8 C9 C10 140.20(15) . . . . ?
O1 C8 C9 C10 -43.94(19) . . . . ?
C14 C9 C10 C11 -2.0(2) . . . . ?
C8 C9 C10 C11 174.12(13) . . . . ?
C14 C9 C10 N1 174.51(13) . . . . ?
C8 C9 C10 N1 -9.4(2) . . . . ?
C9 C10 C11 C12 1.7(2) . . . . ?
N1 C10 C11 C12 -174.82(13) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C10 C11 C12 N2 179.18(12) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
N2 C12 C13 C14 179.63(13) . . . . ?
C12 C13 C14 C9 0.7(2) . . . . ?
C10 C9 C14 C13 0.7(2) . . . . ?
C8 C9 C14 C13 -175.66(13) . . . . ?
C11 C10 N1 O3 131.43(14) . . . . ?
C9 C10 N1 O3 -45.2(2) . . . . ?
C11 C10 N1 O4 -47.7(2) . . . . ?
C9 C10 N1 O4 135.60(15) . . . . ?
C11 C12 N2 O6 -176.03(13) . . . . ?
C13 C12 N2 O6 3.4(2) . . . . ?
C11 C12 N2 O5 3.2(2) . . . . ?
C13 C12 N2 O5 -177.31(13) . . . . ?
O2 C8 O1 C1 -8.6(2) . . . . ?
C9 C8 O1 C1 175.66(12) . . . . ?
C2 C1 O1 C8 -98.96(15) . . . . ?
C5 C1 O1 C8 135.91(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.041

data_jmwnf20
_database_code_depnum_ccdc_archive 'CCDC 265215'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 N2 O5 S'
_chemical_formula_weight         310.32

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'
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'
S S 0.1246 0.1234 '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                   10.3778(8)
_cell_length_b                   12.0317(10)
_cell_length_c                   11.3503(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.395(2)
_cell_angle_gamma                90.00
_cell_volume                     1372.73(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2240
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.36
_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_max          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7185
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2422
_reflns_number_gt                1999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0449P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2422
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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 0.8056(2) 0.27345(15) 0.55508(18) 0.0235(5) Uani 1 1 d . . .
H1 H 0.8834 0.2838 0.6237 0.028 Uiso 1 1 calc R . .
C2 C 0.7354(2) 0.38217(15) 0.52563(19) 0.0261(5) Uani 1 1 d . . .
H2 H 0.6612 0.3822 0.4528 0.031 Uiso 1 1 calc R . .
C3 C 0.8157(2) 0.48706(15) 0.54703(19) 0.0308(5) Uani 1 1 d . . .
H3A H 0.9102 0.4807 0.5844 0.037 Uiso 1 1 calc R . .
H3B H 0.7915 0.5460 0.4873 0.037 Uiso 1 1 calc R . .
C4 C 0.7215(2) 0.46112(17) 0.6236(2) 0.0377(6) Uani 1 1 d . . .
H4A H 0.6404 0.5044 0.6102 0.045 Uiso 1 1 calc R . .
H4B H 0.7591 0.4392 0.7073 0.045 Uiso 1 1 calc R . .
C5 C 0.8501(2) 0.22642(15) 0.45019(18) 0.0239(5) Uani 1 1 d . . .
H2' H 0.7798 0.2166 0.3753 0.029 Uiso 1 1 calc R . .
C6 C 0.9824(2) 0.26393(16) 0.43243(19) 0.0265(5) Uani 1 1 d . . .
H6A H 0.9887 0.2783 0.3500 0.032 Uiso 1 1 calc R . .
H6B H 1.0363 0.3122 0.4937 0.032 Uiso 1 1 calc R . .
C7 C 0.9645(2) 0.14583(17) 0.4672(2) 0.0318(5) Uani 1 1 d . . .
H7A H 1.0076 0.1229 0.5495 0.038 Uiso 1 1 calc R . .
H7B H 0.9601 0.0890 0.4057 0.038 Uiso 1 1 calc R . .
C8 C 0.70913(19) -0.01615(15) 0.56499(16) 0.0196(4) Uani 1 1 d . . .
C9 C 0.72261(19) -0.12970(15) 0.59507(16) 0.0189(4) Uani 1 1 d . . .
C10 C 0.66794(19) -0.21348(15) 0.51544(18) 0.0208(4) Uani 1 1 d . . .
H10 H 0.6783 -0.2877 0.5387 0.025 Uiso 1 1 calc R . .
C11 C 0.59746(18) -0.18366(15) 0.40035(17) 0.0196(4) Uani 1 1 d . . .
C12 C 0.57966(19) -0.07242(15) 0.36566(17) 0.0209(4) Uani 1 1 d . . .
H12 H 0.5309 -0.0539 0.2878 0.025 Uiso 1 1 calc R . .
C13 C 0.63419(19) 0.00961(16) 0.44669(16) 0.0208(4) Uani 1 1 d . . .
H13 H 0.6215 0.0836 0.4231 0.025 Uiso 1 1 calc R . .
N1 N 0.79917(16) -0.16134(14) 0.71537(15) 0.0232(4) Uani 1 1 d . . .
N2 N 0.54220(16) -0.27114(14) 0.31297(16) 0.0255(4) Uani 1 1 d . . .
O1 O 0.70901(14) 0.19954(10) 0.59352(12) 0.0261(3) Uani 1 1 d . . .
O2 O 0.85821(14) -0.08532(11) 0.78107(12) 0.0308(4) Uani 1 1 d . . .
O3 O 0.80318(14) -0.25923(11) 0.74721(13) 0.0298(4) Uani 1 1 d . . .
O4 O 0.56551(15) -0.36875(11) 0.34369(13) 0.0347(4) Uani 1 1 d . . .
O5 O 0.47725(14) -0.24267(11) 0.21161(13) 0.0332(4) Uani 1 1 d . . .
S1 S 0.77318(5) 0.08814(4) 0.67059(4) 0.02457(16) 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 0.0230(11) 0.0206(11) 0.0265(11) -0.0005(8) 0.0053(9) -0.0056(9)
C2 0.0273(12) 0.0216(11) 0.0293(12) 0.0000(9) 0.0072(9) 0.0003(9)
C3 0.0302(13) 0.0220(11) 0.0397(13) 0.0038(10) 0.0079(10) -0.0013(10)
C4 0.0542(16) 0.0260(12) 0.0380(13) -0.0011(10) 0.0210(12) 0.0022(11)
C5 0.0223(11) 0.0205(11) 0.0281(12) -0.0027(8) 0.0050(9) -0.0032(9)
C6 0.0254(12) 0.0253(11) 0.0304(12) 0.0010(9) 0.0096(9) -0.0015(9)
C7 0.0336(14) 0.0258(12) 0.0380(14) 0.0014(9) 0.0127(11) 0.0028(10)
C8 0.0173(10) 0.0214(10) 0.0216(10) -0.0015(8) 0.0078(8) -0.0013(8)
C9 0.0168(11) 0.0231(11) 0.0170(10) 0.0010(8) 0.0047(8) -0.0005(8)
C10 0.0171(10) 0.0177(10) 0.0293(12) 0.0003(8) 0.0089(9) 0.0002(8)
C11 0.0164(10) 0.0219(11) 0.0207(11) -0.0052(8) 0.0053(8) -0.0021(8)
C12 0.0158(10) 0.0279(11) 0.0189(10) 0.0018(9) 0.0039(8) 0.0001(9)
C13 0.0219(11) 0.0191(10) 0.0225(11) 0.0014(8) 0.0073(9) -0.0003(8)
N1 0.0202(9) 0.0269(10) 0.0242(9) 0.0033(8) 0.0084(8) 0.0011(8)
N2 0.0184(9) 0.0294(10) 0.0292(11) -0.0056(8) 0.0066(8) -0.0007(8)
O1 0.0276(8) 0.0189(7) 0.0342(8) -0.0008(6) 0.0123(6) -0.0034(6)
O2 0.0333(9) 0.0335(9) 0.0219(8) -0.0034(6) -0.0003(6) -0.0083(7)
O3 0.0337(9) 0.0261(8) 0.0291(8) 0.0096(6) 0.0072(7) 0.0037(7)
O4 0.0373(10) 0.0195(8) 0.0431(10) -0.0061(7) 0.0020(7) 0.0006(7)
O5 0.0310(9) 0.0382(9) 0.0257(9) -0.0078(7) -0.0019(7) 0.0012(7)
S1 0.0291(3) 0.0217(3) 0.0228(3) -0.0027(2) 0.0062(2) -0.0062(2)

_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 1.485(2) . ?
C1 C5 1.491(3) . ?
C1 C2 1.494(3) . ?
C1 H1 0.9800 . ?
C2 C4 1.496(3) . ?
C2 C3 1.498(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.493(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.506(3) . ?
C5 C7 1.508(3) . ?
C5 H2 0.9800 . ?
C6 C7 1.499(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.407(3) . ?
C8 C13 1.409(3) . ?
C8 S1 1.7484(19) . ?
C9 C10 1.378(3) . ?
C9 N1 1.450(2) . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(3) . ?
C11 N2 1.462(2) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N1 O3 1.2296(19) . ?
N1 O2 1.241(2) . ?
N2 O5 1.229(2) . ?
N2 O4 1.232(2) . ?
O1 S1 1.6479(14) . ?

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 C5 111.90(15) . . ?
O1 C1 C2 105.24(15) . . ?
C5 C1 C2 112.58(16) . . ?
O1 C1 H1 109.0 . . ?
C5 C1 H1 109.0 . . ?
C2 C1 H1 109.0 . . ?
C1 C2 C4 121.42(19) . . ?
C1 C2 C3 118.73(18) . . ?
C4 C2 C3 59.82(13) . . ?
C1 C2 H2 115.2 . . ?
C4 C2 H2 115.2 . . ?
C3 C2 H2 115.2 . . ?
C4 C3 C2 60.02(13) . . ?
C4 C3 H3A 117.8 . . ?
C2 C3 H3A 117.8 . . ?
C4 C3 H3B 117.8 . . ?
C2 C3 H3B 117.8 . . ?
H3A C3 H3B 114.9 . . ?
C3 C4 C2 60.16(13) . . ?
C3 C4 H4A 117.8 . . ?
C2 C4 H4A 117.8 . . ?
C3 C4 H4B 117.8 . . ?
C2 C4 H4B 117.8 . . ?
H4A C4 H4B 114.9 . . ?
C1 C5 C6 117.81(17) . . ?
C1 C5 C7 122.12(18) . . ?
C6 C5 C7 59.63(13) . . ?
C1 C5 H2 115.3 . . ?
C6 C5 H2 115.3 . . ?
C7 C5 H2 115.3 . . ?
C7 C6 C5 60.27(12) . . ?
C7 C6 H6A 117.7 . . ?
C5 C6 H6A 117.7 . . ?
C7 C6 H6B 117.7 . . ?
C5 C6 H6B 117.7 . . ?
H6A C6 H6B 114.9 . . ?
C6 C7 C5 60.10(13) . . ?
C6 C7 H7A 117.8 . . ?
C5 C7 H7A 117.8 . . ?
C6 C7 H7B 117.8 . . ?
C5 C7 H7B 117.8 . . ?
H7A C7 H7B 114.9 . . ?
C9 C8 C13 116.30(17) . . ?
C9 C8 S1 122.19(14) . . ?
C13 C8 S1 121.41(14) . . ?
C10 C9 C8 123.45(18) . . ?
C10 C9 N1 117.74(17) . . ?
C8 C9 N1 118.81(16) . . ?
C11 C10 C9 117.82(17) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C10 C11 C12 121.33(17) . . ?
C10 C11 N2 118.84(17) . . ?
C12 C11 N2 119.83(17) . . ?
C13 C12 C11 119.85(18) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 121.24(18) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
O3 N1 O2 123.61(17) . . ?
O3 N1 C9 119.94(16) . . ?
O2 N1 C9 116.45(15) . . ?
O5 N2 O4 123.66(16) . . ?
O5 N2 C11 117.77(16) . . ?
O4 N2 C11 118.56(17) . . ?
C1 O1 S1 115.46(12) . . ?
O1 S1 C8 100.67(8) . . ?

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
O1 C1 C2 C4 77.9(2) . . . . ?
C5 C1 C2 C4 -159.93(19) . . . . ?
O1 C1 C2 C3 148.25(17) . . . . ?
C5 C1 C2 C3 -89.6(2) . . . . ?
C1 C2 C3 C4 -111.7(2) . . . . ?
C1 C2 C4 C3 107.2(2) . . . . ?
O1 C1 C5 C6 -156.02(16) . . . . ?
C2 C1 C5 C6 85.7(2) . . . . ?
O1 C1 C5 C7 -86.1(2) . . . . ?
C2 C1 C5 C7 155.58(18) . . . . ?
C1 C5 C6 C7 112.8(2) . . . . ?
C1 C5 C7 C6 -105.7(2) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
S1 C8 C9 C10 176.92(15) . . . . ?
C13 C8 C9 N1 179.71(15) . . . . ?
S1 C8 C9 N1 -3.9(2) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
N1 C9 C10 C11 -178.71(16) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C9 C10 C11 N2 178.03(16) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
N2 C11 C12 C13 -178.45(17) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C9 C8 C13 C12 -0.9(3) . . . . ?
S1 C8 C13 C12 -177.39(15) . . . . ?
C10 C9 N1 O3 -6.8(2) . . . . ?
C8 C9 N1 O3 173.98(16) . . . . ?
C10 C9 N1 O2 173.09(17) . . . . ?
C8 C9 N1 O2 -6.2(2) . . . . ?
C10 C11 N2 O5 178.48(17) . . . . ?
C12 C11 N2 O5 -2.4(2) . . . . ?
C10 C11 N2 O4 -3.1(3) . . . . ?
C12 C11 N2 O4 176.06(17) . . . . ?
C5 C1 O1 S1 75.52(18) . . . . ?
C2 C1 O1 S1 -161.91(12) . . . . ?
C1 O1 S1 C8 -111.02(13) . . . . ?
C9 C8 S1 O1 -171.62(15) . . . . ?
C13 C8 S1 O1 4.62(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048

data_jmwnf26
_database_code_depnum_ccdc_archive 'CCDC 265216'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 N3 O7'
_chemical_formula_weight         283.20

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'
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) '

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

_cell_length_a                   6.1596(6)
_cell_length_b                   7.9020(8)
_cell_length_c                   24.235(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1179.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2815
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.26
_exptl_crystal_description       slab
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_max          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7329
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2651
_reflns_number_gt                2383
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0411P)^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    mixed
_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   0.4(11)
_refine_ls_number_reflns         2651
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 1.1217(3) 0.8553(2) 0.17385(7) 0.0286(4) Uani 1 1 d . . .
H1A H 1.0506 0.9052 0.2056 0.034 Uiso 1 1 calc R . .
H1B H 1.0467 0.7514 0.1643 0.034 Uiso 1 1 calc R . .
C2 C 1.3520(3) 0.8197(2) 0.18655(8) 0.0340(4) Uani 1 1 d . . .
H2 H 1.4387 0.9159 0.1994 0.041 Uiso 1 1 calc R . .
C3 C 1.4050(4) 0.6523(3) 0.21140(8) 0.0418(5) Uani 1 1 d . . .
H3A H 1.5193 0.6481 0.2389 0.050 Uiso 1 1 calc R . .
H3B H 1.2869 0.5731 0.2172 0.050 Uiso 1 1 calc R . .
C4 C 1.4674(3) 0.6921(3) 0.15356(9) 0.0437(5) Uani 1 1 d . . .
H4A H 1.6199 0.7115 0.1459 0.052 Uiso 1 1 calc R . .
H4B H 1.3877 0.6365 0.1242 0.052 Uiso 1 1 calc R . .
C5 C 0.9195(3) 1.0372(2) 0.11399(6) 0.0211(3) Uani 1 1 d . . .
C6 C 0.8277(3) 1.1824(2) 0.13834(6) 0.0228(4) Uani 1 1 d . . .
C7 C 0.6295(2) 1.2469(2) 0.12131(6) 0.0228(4) Uani 1 1 d . . .
H7 H 0.5696 1.3414 0.1384 0.027 Uiso 1 1 calc R . .
C8 C 0.5237(3) 1.1677(2) 0.07848(6) 0.0230(4) Uani 1 1 d . . .
C9 C 0.6106(3) 1.0316(2) 0.05035(6) 0.0235(4) Uani 1 1 d . . .
H9 H 0.5409 0.9842 0.0200 0.028 Uiso 1 1 calc R . .
C10 C 0.8051(3) 0.9696(2) 0.06937(6) 0.0222(4) Uani 1 1 d . . .
N1 N 0.9015(2) 0.82553(19) 0.03931(6) 0.0278(3) Uani 1 1 d . . .
N2 N 0.3111(2) 1.23291(19) 0.06038(6) 0.0269(3) Uani 1 1 d . . .
N3 N 0.9457(2) 1.28188(19) 0.18049(5) 0.0272(3) Uani 1 1 d . . .
O1 O 1.11701(17) 0.97438(15) 0.12676(4) 0.0238(3) Uani 1 1 d . . .
O2 O 0.9402(2) 0.69691(17) 0.06486(5) 0.0402(4) Uani 1 1 d . . .
O3 O 0.9322(2) 0.84530(19) -0.01019(5) 0.0415(3) Uani 1 1 d . . .
O4 O 0.2241(2) 1.16151(17) 0.02117(5) 0.0354(3) Uani 1 1 d . . .
O5 O 0.2326(2) 1.35193(17) 0.08565(5) 0.0367(3) Uani 1 1 d . . .
O6 O 0.8913(2) 1.42856(16) 0.18663(5) 0.0384(3) Uani 1 1 d . . .
O7 O 1.0908(2) 1.21371(18) 0.20654(5) 0.0423(4) 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 0.0309(9) 0.0309(9) 0.0238(8) 0.0071(8) 0.0009(7) 0.0051(9)
C2 0.0319(10) 0.0317(10) 0.0383(10) 0.0044(9) -0.0117(8) -0.0013(8)
C3 0.0355(11) 0.0434(12) 0.0466(11) 0.0109(10) -0.0065(10) 0.0049(11)
C4 0.0339(11) 0.0443(13) 0.0529(12) 0.0104(10) 0.0048(9) 0.0077(10)
C5 0.0189(8) 0.0246(8) 0.0199(7) 0.0046(7) 0.0022(6) 0.0002(7)
C6 0.0240(8) 0.0258(9) 0.0186(7) 0.0020(7) 0.0000(6) -0.0011(7)
C7 0.0226(8) 0.0239(9) 0.0218(7) 0.0028(7) 0.0053(7) 0.0026(7)
C8 0.0184(8) 0.0253(9) 0.0251(8) 0.0092(7) 0.0003(6) -0.0015(7)
C9 0.0237(8) 0.0263(9) 0.0203(7) 0.0017(7) -0.0016(7) -0.0050(8)
C10 0.0223(8) 0.0239(9) 0.0202(8) 0.0008(7) 0.0042(6) -0.0004(7)
N1 0.0234(7) 0.0324(9) 0.0275(7) -0.0047(7) -0.0027(6) 0.0029(7)
N2 0.0186(7) 0.0298(8) 0.0325(8) 0.0104(7) 0.0004(6) 0.0008(7)
N3 0.0260(8) 0.0333(8) 0.0223(7) -0.0032(7) -0.0007(6) 0.0025(7)
O1 0.0199(6) 0.0301(7) 0.0215(5) 0.0042(5) -0.0013(5) 0.0041(5)
O2 0.0505(9) 0.0306(7) 0.0394(7) -0.0017(6) -0.0015(6) 0.0123(7)
O3 0.0507(8) 0.0492(8) 0.0246(6) -0.0085(6) 0.0054(6) 0.0094(7)
O4 0.0262(7) 0.0491(9) 0.0309(7) 0.0100(6) -0.0078(5) -0.0016(6)
O5 0.0243(7) 0.0313(7) 0.0543(8) 0.0048(7) 0.0014(6) 0.0064(6)
O6 0.0435(8) 0.0316(7) 0.0403(7) -0.0117(6) -0.0067(7) 0.0039(7)
O7 0.0427(8) 0.0485(9) 0.0356(7) -0.0106(6) -0.0185(7) 0.0104(7)

_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 C2 1.478(3) . ?
C1 O1 1.4792(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.470(3) . ?
C2 C3 1.490(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.487(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.350(2) . ?
C5 C10 1.397(2) . ?
C5 C6 1.409(2) . ?
C6 C7 1.385(2) . ?
C6 N3 1.480(2) . ?
C7 C8 1.376(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(2) . ?
C8 N2 1.474(2) . ?
C9 C10 1.374(2) . ?
C9 H9 0.9300 . ?
C10 N1 1.476(2) . ?
N1 O2 1.2137(19) . ?
N1 O3 1.2245(18) . ?
N2 O5 1.2219(19) . ?
N2 O4 1.2280(18) . ?
N3 O6 1.2156(19) . ?
N3 O7 1.2196(18) . ?

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
C2 C1 O1 107.49(14) . . ?
C2 C1 H1A 110.2 . . ?
O1 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
O1 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C4 C2 C1 118.77(17) . . ?
C4 C2 C3 60.32(14) . . ?
C1 C2 C3 117.63(17) . . ?
C4 C2 H2 116.2 . . ?
C1 C2 H2 116.2 . . ?
C3 C2 H2 116.2 . . ?
C4 C3 C2 59.17(13) . . ?
C4 C3 H3A 117.9 . . ?
C2 C3 H3A 117.9 . . ?
C4 C3 H3B 117.9 . . ?
C2 C3 H3B 117.9 . . ?
H3A C3 H3B 115.0 . . ?
C2 C4 C3 60.50(13) . . ?
C2 C4 H4A 117.7 . . ?
C3 C4 H4A 117.7 . . ?
C2 C4 H4B 117.7 . . ?
C3 C4 H4B 117.7 . . ?
H4A C4 H4B 114.8 . . ?
O1 C5 C10 119.42(15) . . ?
O1 C5 C6 124.45(15) . . ?
C10 C5 C6 115.67(15) . . ?
C7 C6 C5 121.92(15) . . ?
C7 C6 N3 116.29(15) . . ?
C5 C6 N3 121.63(15) . . ?
C8 C7 C6 118.33(16) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C7 C8 C9 122.86(16) . . ?
C7 C8 N2 119.09(15) . . ?
C9 C8 N2 118.02(15) . . ?
C10 C9 C8 116.76(15) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C9 C10 C5 124.26(15) . . ?
C9 C10 N1 117.41(14) . . ?
C5 C10 N1 118.29(14) . . ?
O2 N1 O3 125.20(15) . . ?
O2 N1 C10 118.21(13) . . ?
O3 N1 C10 116.57(14) . . ?
O5 N2 O4 124.70(15) . . ?
O5 N2 C8 118.11(15) . . ?
O4 N2 C8 117.19(14) . . ?
O6 N3 O7 124.03(15) . . ?
O6 N3 C6 117.10(14) . . ?
O7 N3 C6 118.87(14) . . ?
C5 O1 C1 115.37(12) . . ?

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
O1 C1 C2 C4 -81.8(2) . . . . ?
O1 C1 C2 C3 -151.35(16) . . . . ?
C1 C2 C3 C4 109.1(2) . . . . ?
C1 C2 C4 C3 -107.22(19) . . . . ?
O1 C5 C6 C7 176.15(14) . . . . ?
C10 C5 C6 C7 4.0(2) . . . . ?
O1 C5 C6 N3 1.0(2) . . . . ?
C10 C5 C6 N3 -171.13(14) . . . . ?
C5 C6 C7 C8 -1.5(2) . . . . ?
N3 C6 C7 C8 173.91(14) . . . . ?
C6 C7 C8 C9 -2.8(2) . . . . ?
C6 C7 C8 N2 179.05(14) . . . . ?
C7 C8 C9 C10 4.2(2) . . . . ?
N2 C8 C9 C10 -177.69(14) . . . . ?
C8 C9 C10 C5 -1.3(2) . . . . ?
C8 C9 C10 N1 -179.23(15) . . . . ?
O1 C5 C10 C9 -175.16(14) . . . . ?
C6 C5 C10 C9 -2.6(2) . . . . ?
O1 C5 C10 N1 2.7(2) . . . . ?
C6 C5 C10 N1 175.29(14) . . . . ?
C9 C10 N1 O2 -122.77(17) . . . . ?
C5 C10 N1 O2 59.2(2) . . . . ?
C9 C10 N1 O3 55.9(2) . . . . ?
C5 C10 N1 O3 -122.18(17) . . . . ?
C7 C8 N2 O5 -2.7(2) . . . . ?
C9 C8 N2 O5 179.10(15) . . . . ?
C7 C8 N2 O4 178.24(14) . . . . ?
C9 C8 N2 O4 0.0(2) . . . . ?
C7 C6 N3 O6 -18.1(2) . . . . ?
C5 C6 N3 O6 157.35(15) . . . . ?
C7 C6 N3 O7 162.38(14) . . . . ?
C5 C6 N3 O7 -22.2(2) . . . . ?
C10 C5 O1 C1 -101.21(17) . . . . ?
C6 C5 O1 C1 86.94(19) . . . . ?
C2 C1 O1 C5 -172.08(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045