# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Samantha Callear'
_publ_contact_author_email       S.K.CALLEAR@SOTON.AC.UK

_publ_section_title              
;
Co-crystallisation of organic alpha,omega-dicarboxylic
acids with the cyclic amides 2-pyrrolidinone and 2-imidazolidinone.
;
loop_
_publ_author_name
'Samantha Callear'
'Michael B. Hursthouse'
'Terence L. Threlfall'

# Attachment '1.cif'

data_06skc0040p-1
_database_code_depnum_ccdc_archive 'CCDC 717663'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 N2 O6'
_chemical_formula_weight         288.30

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.749(3)
_cell_length_b                   6.541(3)
_cell_length_c                   9.903(5)
_cell_angle_alpha                80.40(2)
_cell_angle_beta                 78.70(2)
_cell_angle_gamma                71.71(3)
_cell_volume                     344.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1224
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             154
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5982
_diffrn_reflns_av_R_equivalents  0.1351
_diffrn_reflns_av_sigmaI/netI    0.1246
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1199
_reflns_number_gt                539
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1151P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1199
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1812
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2185
_refine_ls_wR_factor_gt          0.1665
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.002
_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 0.5761(9) 0.6667(8) 0.1187(5) 0.0553(14) Uani 1 1 d . . .
C2 C 0.5841(9) 0.5703(8) -0.0094(5) 0.0588(15) Uani 1 1 d . . .
H2A H 0.7563 0.4830 -0.0391 0.071 Uiso 1 1 calc R . .
H2B H 0.5371 0.6889 -0.0843 0.071 Uiso 1 1 calc R . .
O1A O 0.7327(6) 0.7864(6) 0.1005(3) 0.0655(11) Uani 1 1 d . . .
H1 H 0.7121 0.8478 0.1718 0.075(18) Uiso 1 1 calc R . .
O1B O 0.4461(7) 0.6409(6) 0.2266(4) 0.0651(11) Uani 1 1 d . . .
C22 C 0.7731(9) 0.0825(8) 0.3525(5) 0.0512(13) Uani 1 1 d . . .
C23 C 0.9746(9) 0.1546(8) 0.2567(5) 0.0566(14) Uani 1 1 d . . .
H23A H 0.9168 0.2298 0.1687 0.068 Uiso 1 1 calc R . .
H23B H 1.1210 0.0291 0.2358 0.068 Uiso 1 1 calc R . .
C24 C 1.0393(9) 0.3098(8) 0.3337(4) 0.0544(14) Uani 1 1 d . . .
H24A H 1.2075 0.2457 0.3592 0.065 Uiso 1 1 calc R . .
H24B H 1.0326 0.4495 0.2754 0.065 Uiso 1 1 calc R . .
C25 C 0.8428(9) 0.3425(7) 0.4636(5) 0.0517(13) Uani 1 1 d . . .
H25A H 0.9209 0.3166 0.5479 0.062 Uiso 1 1 calc R . .
H25B H 0.7273 0.4910 0.4574 0.062 Uiso 1 1 calc R . .
N21 N 0.7144(7) 0.1827(6) 0.4653(4) 0.0514(11) Uani 1 1 d . . .
H21 H 0.6057 0.1546 0.5362 0.021(10) Uiso 1 1 calc R . .
O22 O 0.6732(6) -0.0510(5) 0.3319(3) 0.0608(11) 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 0.066(3) 0.059(3) 0.054(3) -0.013(3) -0.013(3) -0.031(3)
C2 0.076(4) 0.062(3) 0.050(3) -0.018(2) -0.006(3) -0.033(3)
O1A 0.080(2) 0.086(3) 0.051(2) -0.024(2) 0.0011(18) -0.052(2)
O1B 0.077(2) 0.083(3) 0.050(2) -0.0216(18) 0.0044(19) -0.046(2)
C22 0.059(3) 0.056(3) 0.047(3) -0.014(3) -0.003(2) -0.028(3)
C23 0.067(3) 0.061(3) 0.051(3) -0.014(2) -0.003(3) -0.032(3)
C24 0.059(3) 0.065(3) 0.052(3) -0.012(2) -0.002(2) -0.039(3)
C25 0.059(3) 0.057(3) 0.054(3) -0.012(2) -0.006(2) -0.035(3)
N21 0.060(3) 0.058(3) 0.048(2) -0.009(2) 0.000(2) -0.037(2)
O22 0.070(2) 0.072(2) 0.058(2) -0.0242(17) -0.0030(17) -0.043(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 O1B 1.198(6) . ?
C1 O1A 1.337(6) . ?
C1 C2 1.495(6) . ?
C2 C2 1.499(9) 2_665 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O1A H1 0.8400 . ?
C22 O22 1.247(5) . ?
C22 N21 1.322(6) . ?
C22 C23 1.493(7) . ?
C23 C24 1.535(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.532(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.453(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?

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
O1B C1 O1A 122.9(4) . . ?
O1B C1 C2 124.7(4) . . ?
O1A C1 C2 112.5(5) . . ?
C1 C2 C2 113.6(5) . 2_665 ?
C1 C2 H2A 108.9 . . ?
C2 C2 H2A 108.9 2_665 . ?
C1 C2 H2B 108.9 . . ?
C2 C2 H2B 108.9 2_665 . ?
H2A C2 H2B 107.7 . . ?
C1 O1A H1 109.5 . . ?
O22 C22 N21 124.3(4) . . ?
O22 C22 C23 126.4(4) . . ?
N21 C22 C23 109.3(4) . . ?
C22 C23 C24 105.5(4) . . ?
C22 C23 H23A 110.6 . . ?
C24 C23 H23A 110.6 . . ?
C22 C23 H23B 110.6 . . ?
C24 C23 H23B 110.6 . . ?
H23A C23 H23B 108.8 . . ?
C25 C24 C23 105.1(3) . . ?
C25 C24 H24A 110.7 . . ?
C23 C24 H24A 110.7 . . ?
C25 C24 H24B 110.7 . . ?
C23 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?
N21 C25 C24 104.1(3) . . ?
N21 C25 H25A 110.9 . . ?
C24 C25 H25A 110.9 . . ?
N21 C25 H25B 110.9 . . ?
C24 C25 H25B 110.9 . . ?
H25A C25 H25B 109.0 . . ?
C22 N21 C25 115.1(4) . . ?
C22 N21 H21 122.5 . . ?
C25 N21 H21 122.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1A H1 O22 0.84 1.77 2.603(4) 173.8 1_565
N21 H21 O22 0.88 2.07 2.935(5) 165.8 2_656

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.064

# Attachment '10.cif'

data_ssg0306
_database_code_depnum_ccdc_archive 'CCDC 717664'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
10
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H12 N2 O7'
_chemical_formula_weight         236.19

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   P21/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                   5.1062(11)
_cell_length_b                   18.198(4)
_cell_length_c                   10.432(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.060(2)
_cell_angle_gamma                90.00
_cell_volume                     962.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    930
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      25.79

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker SADABS'
# absolute Tmin and Tmax unknown, but SADABS gives ratio as 0.731

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.6710
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        5
_diffrn_reflns_number            7832
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         24.79
_reflns_number_total             1961
_reflns_number_gt                1444
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0627P)²+0.2714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1961
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.6361(4) 0.56576(11) 0.1603(2) 0.0190(5) Uani 1 1 d . . .
C2 C 0.5051(4) 0.49324(11) 0.1877(2) 0.0198(5) Uani 1 1 d . . .
H2 H 0.6266 0.4528 0.1682 0.024 Uiso 1 1 calc R . .
C3 C 0.4862(4) 0.49157(11) 0.3338(2) 0.0210(5) Uani 1 1 d . . .
H3 H 0.6697 0.4908 0.3800 0.025 Uiso 1 1 calc R . .
C4 C 0.3463(4) 0.42246(12) 0.3705(2) 0.0207(5) Uani 1 1 d . . .
O1A O 0.8715(3) 0.57577(8) 0.19328(15) 0.0251(4) Uani 1 1 d . . .
O1B O 0.4758(3) 0.61499(8) 0.10315(15) 0.0234(4) Uani 1 1 d . . .
H1 H 0.5593 0.6540 0.0940 0.048(9) Uiso 1 1 calc R . .
O2 O 0.2592(3) 0.48121(8) 0.11204(14) 0.0229(4) Uani 1 1 d . . .
H2O H 0.1521 0.5140 0.1281 0.034 Uiso 1 1 calc R . .
O3 O 0.3586(3) 0.55493(8) 0.37335(14) 0.0224(4) Uani 1 1 d . . .
H3O H 0.1948 0.5506 0.3538 0.034 Uiso 1 1 calc R . .
O4A O 0.4812(3) 0.36240(8) 0.35347(15) 0.0233(4) Uani 1 1 d . . .
H4 H 0.3971 0.3256 0.3748 0.026(7) Uiso 1 1 calc R . .
O4B O 0.1318(3) 0.42434(8) 0.40880(15) 0.0251(4) Uani 1 1 d . . .
C22 C 0.1237(4) 0.23674(11) 0.5131(2) 0.0204(5) Uani 1 1 d . . .
C24 C -0.1703(4) 0.27754(12) 0.6500(2) 0.0239(5) Uani 1 1 d . . .
H24A H -0.3583 0.2920 0.6331 0.029 Uiso 1 1 calc R . .
H24B H -0.0870 0.3029 0.7286 0.029 Uiso 1 1 calc R . .
C25 C -0.1388(4) 0.19345(12) 0.6615(2) 0.0232(5) Uani 1 1 d . . .
H25A H -0.0980 0.1780 0.7528 0.028 Uiso 1 1 calc R . .
H25B H -0.2999 0.1677 0.6223 0.028 Uiso 1 1 calc R . .
N21 N 0.0843(4) 0.17953(11) 0.58874(18) 0.0250(4) Uani 1 1 d . . .
H21 H 0.1793 0.1390 0.5942 0.081(12) Uiso 1 1 calc R . .
N23 N -0.0299(4) 0.29248(10) 0.53861(19) 0.0263(5) Uani 1 1 d . . .
H23 H -0.0453 0.3336 0.4938 0.044(8) Uiso 1 1 calc R . .
O22 O 0.2864(3) 0.23810(8) 0.43048(15) 0.0232(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 0.0187(10) 0.0220(11) 0.0177(11) -0.0009(8) 0.0079(8) 0.0016(8)
C2 0.0165(10) 0.0222(11) 0.0213(11) -0.0004(8) 0.0047(8) 0.0002(8)
C3 0.0216(11) 0.0218(11) 0.0203(11) 0.0004(9) 0.0058(8) 0.0006(8)
C4 0.0214(10) 0.0236(11) 0.0178(11) 0.0002(9) 0.0050(8) 0.0009(9)
O1A 0.0196(8) 0.0267(8) 0.0298(9) 0.0015(7) 0.0057(6) -0.0013(6)
O1B 0.0216(8) 0.0221(8) 0.0274(9) 0.0042(7) 0.0064(6) 0.0001(6)
O2 0.0200(8) 0.0262(8) 0.0229(8) -0.0022(6) 0.0041(6) -0.0014(6)
O3 0.0222(8) 0.0237(8) 0.0223(8) -0.0020(6) 0.0067(6) 0.0005(6)
O4A 0.0243(8) 0.0210(8) 0.0264(9) 0.0018(7) 0.0106(6) -0.0005(6)
O4B 0.0215(8) 0.0251(8) 0.0306(9) 0.0026(7) 0.0104(6) 0.0006(6)
C22 0.0188(10) 0.0227(11) 0.0201(11) 0.0006(9) 0.0048(9) -0.0001(8)
C24 0.0229(11) 0.0269(12) 0.0233(12) 0.0003(9) 0.0087(9) 0.0002(9)
C25 0.0221(11) 0.0251(11) 0.0237(12) 0.0012(9) 0.0080(9) -0.0002(9)
N21 0.0253(10) 0.0248(10) 0.0274(11) 0.0045(8) 0.0130(8) 0.0025(8)
N23 0.0298(10) 0.0237(10) 0.0283(11) 0.0060(8) 0.0145(8) 0.0053(8)
O22 0.0237(8) 0.0233(8) 0.0244(8) 0.0006(6) 0.0096(6) -0.0002(6)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 O1A 1.222(2) . ?
C1 O1B 1.307(3) . ?
C1 C2 1.522(3) . ?
C2 O2 1.416(2) . ?
C2 C3 1.539(3) . ?
C2 H2 1.0000 . ?
C3 O3 1.411(2) . ?
C3 C4 1.518(3) . ?
C3 H3 1.0000 . ?
C4 O4B 1.212(3) . ?
C4 O4A 1.316(3) . ?
O1B H1 0.8400 . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
O4A H4 0.8400 . ?
C22 O22 1.269(2) . ?
C22 N23 1.329(3) . ?
C22 N21 1.337(3) . ?
C24 N23 1.464(3) . ?
C24 C25 1.542(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.466(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?

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
O1A C1 O1B 124.41(19) . . ?
O1A C1 C2 121.06(19) . . ?
O1B C1 C2 114.51(17) . . ?
O2 C2 C1 114.17(17) . . ?
O2 C2 C3 112.93(16) . . ?
C1 C2 C3 106.58(17) . . ?
O2 C2 H2 107.6 . . ?
C1 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
O3 C3 C4 110.77(17) . . ?
O3 C3 C2 111.18(17) . . ?
C4 C3 C2 110.79(17) . . ?
O3 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
O4B C4 O4A 125.3(2) . . ?
O4B C4 C3 122.15(19) . . ?
O4A C4 C3 112.56(17) . . ?
C1 O1B H1 109.5 . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
C4 O4A H4 109.5 . . ?
O22 C22 N23 125.0(2) . . ?
O22 C22 N21 125.09(19) . . ?
N23 C22 N21 109.93(18) . . ?
N23 C24 C25 100.91(17) . . ?
N23 C24 H24A 111.6 . . ?
C25 C24 H24A 111.6 . . ?
N23 C24 H24B 111.6 . . ?
C25 C24 H24B 111.6 . . ?
H24A C24 H24B 109.4 . . ?
N21 C25 C24 102.22(17) . . ?
N21 C25 H25A 111.3 . . ?
C24 C25 H25A 111.3 . . ?
N21 C25 H25B 111.3 . . ?
C24 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
C22 N21 C25 110.72(18) . . ?
C22 N21 H21 124.6 . . ?
C25 N21 H21 124.6 . . ?
C22 N23 C24 112.09(18) . . ?
C22 N23 H23 124.0 . . ?
C24 N23 H23 124.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4A H4 O22 0.84 1.81 2.636(2) 167.6 .
N23 H23 O4B 0.88 2.13 2.924(2) 150.0 .
O1B H1 O22 0.84 1.75 2.593(2) 176.1 2_655
O2 H2O O1A 0.84 2.00 2.830(2) 167.4 1_455
O3 H3O O1A 0.84 2.25 2.951(2) 141.2 1_455
N21 H21 O2 0.88 2.23 3.059(2) 157.0 4_566

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.79
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.063

# Attachment '11.cif'

data_07skc0026p21c
_database_code_depnum_ccdc_archive 'CCDC 717665'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
11
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 N2 O9'
_chemical_formula_weight         318.24

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   P21/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                   31.3779(13)
_cell_length_b                   12.3307(6)
_cell_length_c                   7.1600(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.968(2)
_cell_angle_gamma                90.00
_cell_volume                     2766.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5433
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21095
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_sigmaI/netI    0.1017
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6257
_reflns_number_gt                3383
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+19.7821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6257
_refine_ls_number_parameters     405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2044
_refine_ls_R_factor_gt           0.1184
_refine_ls_wR_factor_ref         0.2395
_refine_ls_wR_factor_gt          0.1928
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.37286(18) 0.1485(5) -0.0505(8) 0.0209(12) Uani 1 1 d . . .
C2 C 0.33654(17) 0.0985(5) 0.0392(8) 0.0215(12) Uani 1 1 d . . .
H2 H 0.3366 0.0215 0.0431 0.026 Uiso 1 1 calc R . .
C3 C 0.30357(18) 0.1467(5) 0.1160(8) 0.0212(12) Uani 1 1 d . . .
H3 H 0.2836 0.0980 0.1653 0.025 Uiso 1 1 calc R . .
C4 C 0.29265(16) 0.2637(4) 0.1379(8) 0.0191(12) Uani 1 1 d . . .
O1A O 0.39910(12) 0.0807(3) -0.1141(6) 0.0274(10) Uani 1 1 d . . .
H1 H 0.4193 0.1143 -0.1606 0.041 Uiso 1 1 calc R . .
O1B O 0.37735(12) 0.2504(3) -0.0634(6) 0.0259(9) Uani 1 1 d . . .
O4A O 0.31687(12) 0.3397(3) 0.0783(6) 0.0238(9) Uani 1 1 d . . .
H4 H 0.3380 0.3120 0.0294 0.036 Uiso 1 1 calc R . .
O4B O 0.25954(12) 0.2860(3) 0.2173(6) 0.0242(9) Uani 1 1 d . . .
C22 C 0.52104(17) 0.7721(5) 0.2593(8) 0.0217(12) Uani 1 1 d . . .
C24 C 0.47721(17) 0.6282(5) 0.3168(9) 0.0257(13) Uani 1 1 d . . .
H24A H 0.4520 0.6031 0.2402 0.031 Uiso 1 1 calc R . .
H24B H 0.4746 0.6043 0.4477 0.031 Uiso 1 1 calc R . .
C25 C 0.51901(18) 0.5865(5) 0.2374(9) 0.0267(14) Uani 1 1 d . . .
H25A H 0.5331 0.5321 0.3214 0.032 Uiso 1 1 calc R . .
H25B H 0.5137 0.5543 0.1117 0.032 Uiso 1 1 calc R . .
N21 N 0.54438(15) 0.6851(4) 0.2288(7) 0.0259(11) Uani 1 1 d . . .
H21 H 0.5717 0.6866 0.2061 0.031 Uiso 1 1 calc R . .
N23 N 0.48202(15) 0.7453(4) 0.3056(7) 0.0281(12) Uani 1 1 d . . .
H23 H 0.4617 0.7923 0.3268 0.034 Uiso 1 1 calc R . .
O22 O 0.53327(12) 0.8712(3) 0.2446(6) 0.0270(9) Uani 1 1 d . . .
C31 C 0.19862(18) 0.4919(5) 0.3576(8) 0.0232(13) Uani 1 1 d . . .
C32 C 0.18514(17) 0.6072(5) 0.3780(8) 0.0224(13) Uani 1 1 d . . .
H32 H 0.2035 0.6603 0.3296 0.027 Uiso 1 1 calc R . .
C33 C 0.15023(18) 0.6447(5) 0.4563(8) 0.0241(13) Uani 1 1 d . . .
H33 H 0.1478 0.7215 0.4524 0.029 Uiso 1 1 calc R . .
C34 C 0.11452(18) 0.5912(5) 0.5479(8) 0.0237(13) Uani 1 1 d . . .
O31A O 0.17860(12) 0.4129(3) 0.4064(6) 0.0251(9) Uani 1 1 d . . .
O31B O 0.23497(12) 0.4850(3) 0.2748(6) 0.0263(9) Uani 1 1 d . . .
H31 H 0.2444 0.4214 0.2846 0.039 Uiso 1 1 calc R . .
O34A O 0.11208(12) 0.4836(3) 0.5534(6) 0.0264(10) Uani 1 1 d . . .
H34 H 0.1337 0.4567 0.5069 0.040 Uiso 1 1 calc R . .
O34B O 0.08716(12) 0.6458(3) 0.6184(6) 0.0300(10) Uani 1 1 d . . .
C42 C 0.01648(17) 0.4877(5) 1.2179(7) 0.0196(12) Uani 1 1 d . . .
C44 C 0.01793(17) 0.6743(5) 1.2353(8) 0.0231(13) Uani 1 1 d . . .
H44A H 0.0128 0.7155 1.1177 0.028 Uiso 1 1 calc R . .
H44B H 0.0335 0.7208 1.3287 0.028 Uiso 1 1 calc R . .
C45 C -0.02449(18) 0.6320(5) 1.3100(8) 0.0237(13) Uani 1 1 d . . .
H45A H -0.0260 0.6461 1.4456 0.028 Uiso 1 1 calc R . .
H45B H -0.0495 0.6655 1.2425 0.028 Uiso 1 1 calc R . .
N41 N -0.02210(15) 0.5152(4) 1.2713(7) 0.0260(11) Uani 1 1 d . . .
H41 H -0.0434 0.4695 1.2820 0.031 Uiso 1 1 calc R . .
N43 N 0.04128(14) 0.5738(4) 1.2035(7) 0.0208(10) Uani 1 1 d . . .
H43 H 0.0684 0.5710 1.1781 0.025 Uiso 1 1 calc R . .
O42 O 0.02676(12) 0.3892(3) 1.1871(6) 0.0246(9) Uani 1 1 d . . .
C51 C 0.20537(18) 0.5169(5) 0.8443(8) 0.0215(12) Uani 1 1 d . . .
C52 C 0.19495(18) 0.4004(5) 0.8719(8) 0.0235(13) Uani 1 1 d . . .
H52 H 0.2156 0.3510 0.8295 0.028 Uiso 1 1 calc R . .
C53 C 0.16151(18) 0.3543(5) 0.9462(8) 0.0228(13) Uani 1 1 d . . .
H53 H 0.1623 0.2773 0.9493 0.027 Uiso 1 1 calc R . .
C54 C 0.12295(18) 0.4035(5) 1.0254(8) 0.0224(12) Uani 1 1 d . . .
O51A O 0.23826(12) 0.5396(3) 0.7674(6) 0.0257(9) Uani 1 1 d . . .
O51B O 0.17967(12) 0.5937(3) 0.8967(6) 0.0228(9) Uani 1 1 d . . .
H51 H 0.1579 0.5657 0.9401 0.034 Uiso 1 1 calc R . .
O54A O 0.11837(12) 0.5053(3) 1.0334(6) 0.0248(9) Uani 1 1 d . . .
O54B O 0.09609(13) 0.3365(3) 1.0819(6) 0.0303(10) Uani 1 1 d . . .
H54 H 0.0734 0.3692 1.1045 0.046 Uiso 1 1 calc R . .
C61 C 0.38550(17) 0.8446(5) 0.4558(8) 0.0236(13) Uani 1 1 d . . .
C62 C 0.34777(18) 0.8989(5) 0.5326(8) 0.0261(13) Uani 1 1 d . . .
H62 H 0.3492 0.9759 0.5309 0.031 Uiso 1 1 calc R . .
C63 C 0.31242(18) 0.8602(5) 0.6030(8) 0.0226(13) Uani 1 1 d . . .
H63 H 0.2926 0.9132 0.6408 0.027 Uiso 1 1 calc R . .
C64 C 0.29965(17) 0.7455(5) 0.6308(8) 0.0224(12) Uani 1 1 d . . .
O61A O 0.38853(13) 0.7383(3) 0.4492(7) 0.0338(11) Uani 1 1 d . . .
H61 H 0.3654 0.7104 0.4786 0.051 Uiso 1 1 calc R . .
O61B O 0.41395(14) 0.9014(4) 0.3985(7) 0.0368(11) Uani 1 1 d . . .
O64A O 0.32102(13) 0.6660(3) 0.5868(6) 0.0295(10) Uani 1 1 d . . .
O64B O 0.26277(12) 0.7367(3) 0.7055(6) 0.0257(9) Uani 1 1 d . . .
H64 H 0.2573 0.6709 0.7226 0.039 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
C1 0.023(3) 0.016(3) 0.025(3) 0.001(2) 0.003(2) 0.001(2)
C2 0.020(3) 0.017(3) 0.028(3) 0.002(2) 0.003(2) 0.001(2)
C3 0.023(3) 0.017(3) 0.024(3) 0.001(2) 0.004(2) -0.005(2)
C4 0.014(3) 0.019(3) 0.024(3) -0.002(2) 0.000(2) -0.002(2)
O1A 0.019(2) 0.022(2) 0.042(3) 0.0009(19) 0.0110(19) 0.0022(17)
O1B 0.020(2) 0.024(2) 0.034(2) 0.0024(18) 0.0075(17) 0.0025(18)
O4A 0.021(2) 0.016(2) 0.035(2) 0.0014(17) 0.0100(18) -0.0032(17)
O4B 0.025(2) 0.019(2) 0.029(2) 0.0012(17) 0.0062(17) 0.0022(18)
C22 0.017(3) 0.024(3) 0.025(3) 0.003(2) 0.004(2) 0.001(2)
C24 0.018(3) 0.024(3) 0.035(3) 0.000(3) 0.004(2) -0.008(2)
C25 0.026(3) 0.022(3) 0.033(3) -0.004(3) 0.006(3) -0.007(3)
N21 0.021(2) 0.015(3) 0.042(3) -0.003(2) 0.011(2) 0.001(2)
N23 0.022(3) 0.022(3) 0.041(3) -0.001(2) 0.013(2) 0.000(2)
O22 0.023(2) 0.018(2) 0.041(3) 0.0011(18) 0.0103(18) -0.0006(17)
C31 0.021(3) 0.024(3) 0.024(3) -0.001(2) 0.002(2) 0.001(3)
C32 0.021(3) 0.017(3) 0.030(3) 0.005(2) 0.004(2) -0.002(2)
C33 0.022(3) 0.013(3) 0.038(3) 0.002(2) 0.001(3) 0.000(2)
C34 0.019(3) 0.024(3) 0.028(3) -0.001(2) 0.001(2) 0.001(3)
O31A 0.024(2) 0.016(2) 0.036(2) -0.0017(18) 0.0113(18) -0.0024(17)
O31B 0.019(2) 0.022(2) 0.039(3) -0.0006(19) 0.0118(18) 0.0016(18)
O34A 0.021(2) 0.021(2) 0.038(3) 0.0019(18) 0.0118(19) -0.0007(17)
O34B 0.021(2) 0.027(2) 0.043(3) -0.002(2) 0.0114(19) 0.0044(19)
C42 0.020(3) 0.021(3) 0.018(3) 0.004(2) -0.002(2) -0.001(2)
C44 0.022(3) 0.020(3) 0.028(3) 0.002(2) 0.005(2) 0.002(2)
C45 0.023(3) 0.025(3) 0.024(3) -0.003(2) 0.004(2) 0.001(3)
N41 0.018(2) 0.026(3) 0.036(3) -0.001(2) 0.010(2) -0.004(2)
N43 0.015(2) 0.016(2) 0.033(3) 0.000(2) 0.0068(19) 0.0024(19)
O42 0.022(2) 0.018(2) 0.035(2) -0.0019(17) 0.0082(18) -0.0005(17)
C51 0.019(3) 0.026(3) 0.019(3) -0.001(2) 0.000(2) 0.005(2)
C52 0.024(3) 0.017(3) 0.030(3) 0.000(2) 0.010(2) 0.008(2)
C53 0.029(3) 0.013(3) 0.027(3) -0.002(2) 0.008(3) 0.007(2)
C54 0.021(3) 0.020(3) 0.025(3) -0.002(2) 0.000(2) 0.002(2)
O51A 0.017(2) 0.028(2) 0.032(2) 0.0012(19) 0.0097(17) 0.0018(18)
O51B 0.021(2) 0.014(2) 0.034(2) 0.0005(17) 0.0095(18) 0.0003(16)
O54A 0.021(2) 0.020(2) 0.035(2) -0.0004(17) 0.0087(18) 0.0036(17)
O54B 0.021(2) 0.020(2) 0.051(3) 0.002(2) 0.011(2) -0.0002(18)
C61 0.017(3) 0.026(3) 0.027(3) 0.002(3) -0.006(2) 0.002(3)
C62 0.024(3) 0.021(3) 0.034(3) 0.001(3) 0.012(3) 0.003(3)
C63 0.027(3) 0.018(3) 0.023(3) -0.006(2) 0.005(2) 0.009(2)
C64 0.015(3) 0.030(3) 0.023(3) 0.002(3) 0.005(2) -0.003(3)
O61A 0.025(2) 0.025(2) 0.053(3) -0.004(2) 0.016(2) 0.0020(19)
O61B 0.031(2) 0.031(3) 0.051(3) 0.000(2) 0.015(2) -0.008(2)
O64A 0.023(2) 0.023(2) 0.044(3) -0.0037(19) 0.013(2) 0.0015(18)
O64B 0.020(2) 0.018(2) 0.040(2) -0.0016(19) 0.0081(18) 0.0006(17)

_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 O1B 1.269(7) . ?
C1 O1A 1.274(7) . ?
C1 C2 1.472(8) . ?
C2 C3 1.336(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.492(8) . ?
C3 H3 0.9500 . ?
C4 O4B 1.241(6) . ?
C4 O4A 1.294(6) . ?
O1A H1 0.8400 . ?
O4A H4 0.8400 . ?
C22 O22 1.287(7) . ?
C22 N21 1.324(7) . ?
C22 N23 1.327(7) . ?
C24 N23 1.454(7) . ?
C24 C25 1.545(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.456(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C31 O31A 1.220(7) . ?
C31 O31B 1.315(7) . ?
C31 C32 1.492(8) . ?
C32 C33 1.339(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.482(8) . ?
C33 H33 0.9500 . ?
C34 O34B 1.221(7) . ?
C34 O34A 1.329(7) . ?
O31B H31 0.8400 . ?
O34A H34 0.8400 . ?
C42 O42 1.278(7) . ?
C42 N43 1.324(7) . ?
C42 N41 1.332(7) . ?
C44 N43 1.463(7) . ?
C44 C45 1.550(7) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 N41 1.468(7) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
N41 H41 0.8800 . ?
N43 H43 0.8800 . ?
C51 O51A 1.227(7) . ?
C51 O51B 1.311(6) . ?
C51 C52 1.489(8) . ?
C52 C53 1.328(8) . ?
C52 H52 0.9500 . ?
C53 C54 1.492(8) . ?
C53 H53 0.9500 . ?
C54 O54B 1.262(7) . ?
C54 O54A 1.265(7) . ?
O51B H51 0.8400 . ?
O54B H54 0.8400 . ?
C61 O61B 1.222(7) . ?
C61 O61A 1.316(7) . ?
C61 C62 1.490(8) . ?
C62 C63 1.331(8) . ?
C62 H62 0.9500 . ?
C63 C64 1.487(8) . ?
C63 H63 0.9500 . ?
C64 O64A 1.237(7) . ?
C64 O64B 1.304(6) . ?
O61A H61 0.8400 . ?
O64B H64 0.8400 . ?

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
O1B C1 O1A 123.2(5) . . ?
O1B C1 C2 122.6(5) . . ?
O1A C1 C2 114.2(5) . . ?
C3 C2 C1 128.8(5) . . ?
C3 C2 H2 115.6 . . ?
C1 C2 H2 115.6 . . ?
C2 C3 C4 131.3(5) . . ?
C2 C3 H3 114.3 . . ?
C4 C3 H3 114.3 . . ?
O4B C4 O4A 120.7(5) . . ?
O4B C4 C3 117.7(5) . . ?
O4A C4 C3 121.6(5) . . ?
C1 O1A H1 109.5 . . ?
C4 O4A H4 109.5 . . ?
O22 C22 N21 125.9(5) . . ?
O22 C22 N23 122.7(5) . . ?
N21 C22 N23 111.4(5) . . ?
N23 C24 C25 102.6(4) . . ?
N23 C24 H24A 111.3 . . ?
C25 C24 H24A 111.3 . . ?
N23 C24 H24B 111.3 . . ?
C25 C24 H24B 111.3 . . ?
H24A C24 H24B 109.2 . . ?
N21 C25 C24 102.4(5) . . ?
N21 C25 H25A 111.3 . . ?
C24 C25 H25A 111.3 . . ?
N21 C25 H25B 111.3 . . ?
C24 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
C22 N21 C25 111.2(5) . . ?
C22 N21 H21 124.4 . . ?
C25 N21 H21 124.4 . . ?
C22 N23 C24 111.2(5) . . ?
C22 N23 H23 124.4 . . ?
C24 N23 H23 124.4 . . ?
O31A C31 O31B 123.3(5) . . ?
O31A C31 C32 125.4(5) . . ?
O31B C31 C32 111.3(5) . . ?
C33 C32 C31 127.8(5) . . ?
C33 C32 H32 116.1 . . ?
C31 C32 H32 116.1 . . ?
C32 C33 C34 133.2(5) . . ?
C32 C33 H33 113.4 . . ?
C34 C33 H33 113.4 . . ?
O34B C34 O34A 119.7(5) . . ?
O34B C34 C33 120.0(5) . . ?
O34A C34 C33 120.3(5) . . ?
C31 O31B H31 109.5 . . ?
C34 O34A H34 109.5 . . ?
O42 C42 N43 126.4(5) . . ?
O42 C42 N41 122.2(5) . . ?
N43 C42 N41 111.3(5) . . ?
N43 C44 C45 102.4(4) . . ?
N43 C44 H44A 111.3 . . ?
C45 C44 H44A 111.3 . . ?
N43 C44 H44B 111.3 . . ?
C45 C44 H44B 111.3 . . ?
H44A C44 H44B 109.2 . . ?
N41 C45 C44 102.2(4) . . ?
N41 C45 H45A 111.3 . . ?
C44 C45 H45A 111.3 . . ?
N41 C45 H45B 111.3 . . ?
C44 C45 H45B 111.3 . . ?
H45A C45 H45B 109.2 . . ?
C42 N41 C45 111.1(5) . . ?
C42 N41 H41 124.4 . . ?
C45 N41 H41 124.4 . . ?
C42 N43 C44 111.5(4) . . ?
C42 N43 H43 124.3 . . ?
C44 N43 H43 124.3 . . ?
O51A C51 O51B 120.5(5) . . ?
O51A C51 C52 118.4(5) . . ?
O51B C51 C52 121.1(5) . . ?
C53 C52 C51 130.5(5) . . ?
C53 C52 H52 114.7 . . ?
C51 C52 H52 114.7 . . ?
C52 C53 C54 130.6(5) . . ?
C52 C53 H53 114.7 . . ?
C54 C53 H53 114.7 . . ?
O54B C54 O54A 123.7(5) . . ?
O54B C54 C53 115.1(5) . . ?
O54A C54 C53 121.2(5) . . ?
C51 O51B H51 109.5 . . ?
C54 O54B H54 109.5 . . ?
O61B C61 O61A 120.3(5) . . ?
O61B C61 C62 118.3(6) . . ?
O61A C61 C62 121.4(5) . . ?
C63 C62 C61 132.3(6) . . ?
C63 C62 H62 113.9 . . ?
C61 C62 H62 113.9 . . ?
C62 C63 C64 128.9(5) . . ?
C62 C63 H63 115.6 . . ?
C64 C63 H63 115.6 . . ?
O64A C64 O64B 122.9(5) . . ?
O64A C64 C63 124.5(5) . . ?
O64B C64 C63 112.6(5) . . ?
C61 O61A H61 109.5 . . ?
C64 O64B H64 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4A H4 O1B 0.84 1.62 2.458(5) 176.1 .
N23 H23 O61B 0.88 2.10 2.976(7) 175.7 .
N23 H23 O61A 0.88 2.59 3.160(6) 123.6 .
O31B H31 O4B 0.84 1.81 2.611(5) 159.4 .
O34A H34 O31A 0.84 1.70 2.540(5) 175.1 .
N43 H43 O54A 0.88 2.09 2.890(6) 151.3 .
O51B H51 O54A 0.84 1.62 2.458(5) 175.4 .
O54B H54 O42 0.84 1.63 2.427(5) 158.4 .
O61A H61 O64A 0.84 1.72 2.543(6) 167.1 .
O64B H64 O51A 0.84 1.76 2.594(6) 171.6 .
O1A H1 O22 0.84 1.64 2.436(5) 156.2 3_665
N21 H21 O1B 0.88 2.09 2.892(6) 150.9 3_665
N41 H41 O34B 0.88 2.13 2.984(6) 164.5 3_567
N41 H41 O34A 0.88 2.58 3.149(6) 123.5 3_567

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.097

# Attachment '2.cif'

data_06skc0081p21n
_database_code_depnum_ccdc_archive 'CCDC 717666'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 N2 O6'
_chemical_formula_weight         286.28

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   P21/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                   11.6287(3)
_cell_length_b                   5.1904(2)
_cell_length_c                   11.9417(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.971(2)
_cell_angle_gamma                90.00
_cell_volume                     681.62(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1678
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9822
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7393
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1553
_reflns_number_gt                1239
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0038P)²+0.7980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1553
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.35614(17) 0.1183(4) 0.02918(16) 0.0230(4) Uani 1 1 d . . .
C2 C 0.45781(17) -0.0467(4) 0.01940(16) 0.0234(4) Uani 1 1 d . . .
H2 H 0.4611 -0.2228 0.0418 0.028 Uiso 1 1 calc R . .
O1A O 0.33254(12) 0.3316(3) -0.01544(13) 0.0281(4) Uani 1 1 d . . .
O1B O 0.29561(13) 0.0038(3) 0.09037(12) 0.0276(3) Uani 1 1 d . . .
H1 H 0.2344 0.0927 0.0879 0.083(11) Uiso 1 1 calc R . .
C22 C 0.52925(17) 0.2932(4) -0.37828(16) 0.0213(4) Uani 1 1 d . . .
C23 C 0.54729(17) 0.4965(4) -0.28504(17) 0.0227(4) Uani 1 1 d . . .
H23A H 0.5719 0.6622 -0.3115 0.027 Uiso 1 1 calc R . .
H23B H 0.6097 0.4435 -0.2102 0.027 Uiso 1 1 calc R . .
C24 C 0.42126(17) 0.5179(4) -0.26975(17) 0.0233(4) Uani 1 1 d . . .
H24A H 0.4288 0.5433 -0.1855 0.028 Uiso 1 1 calc R . .
H24B H 0.3744 0.6631 -0.3167 0.028 Uiso 1 1 calc R . .
C25 C 0.36002(17) 0.2592(4) -0.31571(17) 0.0216(4) Uani 1 1 d . . .
H25A H 0.3695 0.1363 -0.2499 0.026 Uiso 1 1 calc R . .
H25B H 0.2724 0.2824 -0.3595 0.026 Uiso 1 1 calc R . .
N21 N 0.42544(14) 0.1715(3) -0.39402(14) 0.0222(4) Uani 1 1 d . . .
H21 H 0.3983 0.0488 -0.4469 0.026(6) Uiso 1 1 calc R . .
O22 O 0.60204(13) 0.2411(3) -0.43283(13) 0.0292(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 0.0200(9) 0.0276(10) 0.0186(9) -0.0033(8) 0.0023(7) 0.0026(8)
C2 0.0233(9) 0.0238(10) 0.0202(9) -0.0012(8) 0.0030(7) -0.0005(8)
O1A 0.0262(7) 0.0298(8) 0.0312(8) 0.0020(7) 0.0133(6) 0.0007(6)
O1B 0.0267(8) 0.0265(8) 0.0318(8) 0.0041(6) 0.0123(6) 0.0064(6)
C22 0.0242(9) 0.0200(9) 0.0208(9) 0.0001(8) 0.0087(8) -0.0002(8)
C23 0.0248(10) 0.0216(10) 0.0224(9) -0.0037(8) 0.0086(8) -0.0013(8)
C24 0.0279(10) 0.0203(10) 0.0221(9) -0.0012(8) 0.0087(8) 0.0024(8)
C25 0.0230(10) 0.0233(10) 0.0203(9) 0.0015(8) 0.0097(7) -0.0003(8)
N21 0.0238(8) 0.0218(8) 0.0224(8) -0.0046(7) 0.0092(7) -0.0054(7)
O22 0.0289(8) 0.0303(8) 0.0334(8) -0.0102(7) 0.0170(6) -0.0076(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 O1A 1.220(2) . ?
C1 O1B 1.310(2) . ?
C1 C2 1.495(3) . ?
C2 C2 1.307(4) 3_655 ?
C2 H2 0.9500 . ?
O1B H1 0.8400 . ?
C22 O22 1.254(2) . ?
C22 N21 1.321(2) . ?
C22 C23 1.499(3) . ?
C23 C24 1.539(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.535(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.457(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?

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
O1A C1 O1B 124.71(18) . . ?
O1A C1 C2 123.84(18) . . ?
O1B C1 C2 111.44(17) . . ?
C2 C2 C1 121.3(2) 3_655 . ?
C2 C2 H2 119.4 3_655 . ?
C1 C2 H2 119.4 . . ?
C1 O1B H1 109.5 . . ?
O22 C22 N21 124.27(18) . . ?
O22 C22 C23 125.64(17) . . ?
N21 C22 C23 110.08(16) . . ?
C22 C23 C24 103.31(15) . . ?
C22 C23 H23A 111.1 . . ?
C24 C23 H23A 111.1 . . ?
C22 C23 H23B 111.1 . . ?
C24 C23 H23B 111.1 . . ?
H23A C23 H23B 109.1 . . ?
C25 C24 C23 104.10(15) . . ?
C25 C24 H24A 110.9 . . ?
C23 C24 H24A 110.9 . . ?
C25 C24 H24B 110.9 . . ?
C23 C24 H24B 110.9 . . ?
H24A C24 H24B 109.0 . . ?
N21 C25 C24 102.97(14) . . ?
N21 C25 H25A 111.2 . . ?
C24 C25 H25A 111.2 . . ?
N21 C25 H25B 111.2 . . ?
C24 C25 H25B 111.2 . . ?
H25A C25 H25B 109.1 . . ?
C22 N21 C25 113.77(16) . . ?
C22 N21 H21 123.1 . . ?
C25 N21 H21 123.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1B H1 O22 0.84 1.71 2.5476(19) 173.5 4_566
N21 H21 O22 0.88 2.08 2.921(2) 159.9 3_654

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054

# Attachment '3.cif'

data_06skc0068p21c
_database_code_depnum_ccdc_archive 'CCDC 717667'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H14 N4 O6'
_chemical_formula_weight         262.23

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   P21/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                   8.322(4)
_cell_length_b                   11.203(5)
_cell_length_c                   11.915(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.79(3)
_cell_angle_gamma                90.00
_cell_volume                     1100.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2546
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9865
_exptl_absorpt_correction_T_max  0.9986
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15954
_diffrn_reflns_av_R_equivalents  0.1842
_diffrn_reflns_av_sigmaI/netI    0.1022
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1934
_reflns_number_gt                1265
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+9.0267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1934
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2012
_refine_ls_R_factor_gt           0.1421
_refine_ls_wR_factor_ref         0.2343
_refine_ls_wR_factor_gt          0.2116
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.243
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 -0.2026(9) -0.1130(7) 0.4687(6) 0.0186(12) Uani 1 1 d . . .
C2 C -0.2938(9) -0.1534(7) 0.5644(6) 0.0186(12) Uani 1 1 d . . .
O1A O -0.1413(6) -0.1852(5) 0.4105(4) 0.0223(13) Uani 1 1 d . . .
O1B O -0.2003(6) 0.0022(5) 0.4570(5) 0.0203(13) Uani 1 1 d . . .
H1 H -0.1438 0.0202 0.4062 0.030 Uiso 1 1 calc R . .
O2A O -0.2945(7) -0.2683(5) 0.5775(4) 0.0209(13) Uani 1 1 d . . .
H2 H -0.3415 -0.2854 0.6335 0.031 Uiso 1 1 calc R . .
O2B O -0.3593(6) -0.0840(5) 0.6199(4) 0.0214(13) Uani 1 1 d . . .
C22 C -0.0253(10) -0.0242(8) 0.7596(7) 0.024(2) Uani 1 1 d . . .
C24 C -0.0981(9) 0.1354(7) 0.8617(6) 0.0200(13) Uani 1 1 d . . .
H24A H -0.1758 0.2018 0.8439 0.024 Uiso 1 1 calc R . .
H24B H -0.0094 0.1615 0.9204 0.024 Uiso 1 1 calc R . .
C25 C -0.1828(10) 0.0220(7) 0.8983(7) 0.0200(13) Uani 1 1 d . . .
H25A H -0.1701 0.0139 0.9818 0.024 Uiso 1 1 calc R . .
H25B H -0.2995 0.0210 0.8679 0.024 Uiso 1 1 calc R . .
N21 N -0.0932(8) -0.0699(6) 0.8465(5) 0.0219(16) Uani 1 1 d . . .
H21 H -0.0847 -0.1447 0.8689 0.026 Uiso 1 1 calc R . .
N23 N -0.0357(8) 0.0918(6) 0.7603(6) 0.0268(18) Uani 1 1 d . . .
H23 H -0.0085 0.1383 0.7064 0.032 Uiso 1 1 calc R . .
O22 O 0.0395(7) -0.0884(5) 0.6900(4) 0.0231(14) Uani 1 1 d . . .
C32 C -0.5205(9) -0.2108(7) 0.2907(6) 0.0173(19) Uani 1 1 d . . .
C34 C -0.6098(10) -0.3733(8) 0.3830(6) 0.024(2) Uani 1 1 d . . .
H34A H -0.5251 -0.4121 0.4372 0.028 Uiso 1 1 calc R . .
H34B H -0.6995 -0.4304 0.3615 0.028 Uiso 1 1 calc R . .
C35 C -0.6704(10) -0.2591(7) 0.4315(7) 0.025(2) Uani 1 1 d . . .
H35A H -0.7889 -0.2500 0.4105 0.030 Uiso 1 1 calc R . .
H35B H -0.6443 -0.2574 0.5151 0.030 Uiso 1 1 calc R . .
N31 N -0.5828(8) -0.1674(6) 0.3796(5) 0.0196(15) Uani 1 1 d . . .
H31 H -0.5720 -0.0932 0.4035 0.024 Uiso 1 1 calc R . .
N33 N -0.5444(8) -0.3293(6) 0.2851(5) 0.0206(16) Uani 1 1 d . . .
H33 H -0.5229 -0.3745 0.2286 0.025 Uiso 1 1 calc R . .
O32 O -0.4552(6) -0.1510(5) 0.2210(4) 0.0226(13) 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 0.013(3) 0.023(3) 0.019(3) -0.007(3) -0.004(2) 0.001(2)
C2 0.013(3) 0.023(3) 0.019(3) -0.007(3) -0.004(2) 0.001(2)
O1A 0.027(3) 0.019(3) 0.024(3) -0.004(2) 0.013(2) 0.004(3)
O1B 0.021(3) 0.014(3) 0.029(3) -0.001(2) 0.016(3) -0.001(2)
O2A 0.022(3) 0.018(3) 0.023(3) -0.001(2) 0.004(2) -0.010(2)
O2B 0.023(3) 0.022(3) 0.021(3) -0.004(2) 0.011(3) -0.003(3)
C22 0.021(5) 0.025(5) 0.025(5) 0.006(4) 0.000(4) 0.000(4)
C24 0.021(3) 0.014(3) 0.025(3) -0.004(3) 0.002(3) 0.003(3)
C25 0.021(3) 0.014(3) 0.025(3) -0.004(3) 0.002(3) 0.003(3)
N21 0.025(4) 0.020(4) 0.022(4) 0.008(3) 0.008(3) 0.007(3)
N23 0.042(5) 0.019(4) 0.021(4) 0.004(3) 0.010(3) 0.000(3)
O22 0.034(3) 0.020(3) 0.017(3) -0.004(3) 0.009(3) 0.006(3)
C32 0.009(4) 0.017(5) 0.024(5) -0.010(4) -0.003(4) 0.004(3)
C34 0.018(4) 0.033(5) 0.021(4) -0.001(4) 0.006(4) 0.005(4)
C35 0.021(5) 0.029(5) 0.026(5) 0.003(4) 0.005(4) 0.001(4)
N31 0.023(4) 0.014(4) 0.022(4) 0.000(3) 0.005(3) 0.001(3)
N33 0.024(4) 0.020(4) 0.019(4) -0.007(3) 0.006(3) -0.005(3)
O32 0.025(3) 0.021(3) 0.021(3) 0.003(2) 0.000(3) -0.001(3)

_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 O1A 1.221(9) . ?
C1 O1B 1.298(9) . ?
C1 C2 1.522(10) . ?
C2 O2B 1.199(9) . ?
C2 O2A 1.297(9) . ?
O1B H1 0.8400 . ?
O2A H2 0.8400 . ?
C22 O22 1.272(10) . ?
C22 N23 1.303(11) . ?
C22 N21 1.346(10) . ?
C24 N23 1.462(9) . ?
C24 C25 1.544(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.457(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C32 O32 1.248(9) . ?
C32 N31 1.333(9) . ?
C32 N33 1.343(10) . ?
C34 N33 1.439(10) . ?
C34 C35 1.517(11) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 N31 1.446(10) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
N31 H31 0.8800 . ?
N33 H33 0.8800 . ?

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
O1A C1 O1B 125.8(7) . . ?
O1A C1 C2 121.1(7) . . ?
O1B C1 C2 113.1(7) . . ?
O2B C2 O2A 124.5(7) . . ?
O2B C2 C1 122.1(7) . . ?
O2A C2 C1 113.4(7) . . ?
C1 O1B H1 109.5 . . ?
C2 O2A H2 109.5 . . ?
O22 C22 N23 127.1(8) . . ?
O22 C22 N21 123.1(8) . . ?
N23 C22 N21 109.8(8) . . ?
N23 C24 C25 100.7(6) . . ?
N23 C24 H24A 111.6 . . ?
C25 C24 H24A 111.6 . . ?
N23 C24 H24B 111.6 . . ?
C25 C24 H24B 111.6 . . ?
H24A C24 H24B 109.4 . . ?
N21 C25 C24 100.5(6) . . ?
N21 C25 H25A 111.7 . . ?
C24 C25 H25A 111.7 . . ?
N21 C25 H25B 111.7 . . ?
C24 C25 H25B 111.7 . . ?
H25A C25 H25B 109.4 . . ?
C22 N21 C25 110.5(7) . . ?
C22 N21 H21 124.8 . . ?
C25 N21 H21 124.8 . . ?
C22 N23 C24 111.7(7) . . ?
C22 N23 H23 124.1 . . ?
C24 N23 H23 124.1 . . ?
O32 C32 N31 125.8(7) . . ?
O32 C32 N33 125.0(7) . . ?
N31 C32 N33 109.2(7) . . ?
N33 C34 C35 101.7(7) . . ?
N33 C34 H34A 111.4 . . ?
C35 C34 H34A 111.4 . . ?
N33 C34 H34B 111.4 . . ?
C35 C34 H34B 111.4 . . ?
H34A C34 H34B 109.3 . . ?
N31 C35 C34 102.9(6) . . ?
N31 C35 H35A 111.2 . . ?
C34 C35 H35A 111.2 . . ?
N31 C35 H35B 111.2 . . ?
C34 C35 H35B 111.2 . . ?
H35A C35 H35B 109.1 . . ?
C32 N31 C35 110.7(7) . . ?
C32 N31 H31 124.6 . . ?
C35 N31 H31 124.6 . . ?
C32 N33 C34 111.6(6) . . ?
C32 N33 H33 124.2 . . ?
C34 N33 H33 124.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1B H1 O22 0.84 1.71 2.535(8) 167.3 3_556
N23 H23 O1A 0.88 2.06 2.867(8) 152.1 3_556
O2A H2 O32 0.84 1.66 2.480(8) 164.4 4_556
N21 H21 O1A 0.88 2.04 2.890(8) 162.2 4_556
N31 H31 O2B 0.88 2.07 2.858(8) 147.9 3_456
N33 H33 O2B 0.88 2.06 2.831(8) 146.5 4

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.093

# Attachment '4.cif'

data_ssf1338
_database_code_depnum_ccdc_archive 'CCDC 717668'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H18 N4 O6'
_chemical_formula_weight         290.28

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5097(15)
_cell_length_b                   9.529(2)
_cell_length_c                   13.030(3)
_cell_angle_alpha                104.839(3)
_cell_angle_beta                 91.938(3)
_cell_angle_gamma                95.093(3)
_cell_volume                     657.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    913
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      29.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.6905
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        5
_diffrn_reflns_number            5694
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         26.64
_reflns_number_total             2909
_reflns_number_gt                2337
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0846P)²+0.3023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2909
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.0960(3) 0.32238(17) 0.90949(13) 0.0175(3) Uani 1 1 d . . .
C2 C -0.0540(3) 0.42133(17) 0.98461(13) 0.0184(4) Uani 1 1 d . . .
H2A H -0.0702 0.3868 1.0498 0.022 Uiso 1 1 calc R . .
H2B H -0.2197 0.4153 0.9510 0.022 Uiso 1 1 calc R . .
O1A O 0.0212(2) 0.18438(13) 0.89571(10) 0.0232(3) Uani 1 1 d . . .
H1 H 0.1091 0.1331 0.8529 0.035 Uiso 1 1 calc R . .
O1B O 0.2693(2) 0.36534(13) 0.86537(10) 0.0252(3) Uani 1 1 d . . .
C22 C 0.5970(3) -0.01663(18) 0.29276(13) 0.0190(3) Uani 1 1 d . . .
C24 C 0.2806(3) 0.04334(19) 0.40366(14) 0.0214(4) Uani 1 1 d . . .
H24A H 0.1433 0.0823 0.3727 0.026 Uiso 1 1 calc R . .
H24B H 0.2789 0.0735 0.4822 0.026 Uiso 1 1 calc R . .
C25 C 0.2681(3) -0.12373(19) 0.36197(14) 0.0225(4) Uani 1 1 d . . .
H25A H 0.3026 -0.1700 0.4201 0.027 Uiso 1 1 calc R . .
H25B H 0.1063 -0.1653 0.3266 0.027 Uiso 1 1 calc R . .
N21 N 0.4589(3) -0.14198(17) 0.28625(13) 0.0280(4) Uani 1 1 d . . .
H21 H 0.4809 -0.2256 0.2415 0.034 Uiso 1 1 calc R . .
N23 N 0.5132(3) 0.09167(16) 0.36767(12) 0.0225(3) Uani 1 1 d . . .
H23 H 0.5894 0.1799 0.3916 0.027 Uiso 1 1 calc R . .
O22 O 0.7753(2) 0.00200(13) 0.23943(10) 0.0236(3) Uani 1 1 d . . .
C31 C 0.2363(3) 0.50094(17) 0.59371(13) 0.0178(3) Uani 1 1 d . . .
C32 C 0.4099(3) 0.44165(17) 0.51072(13) 0.0185(3) Uani 1 1 d . . .
H32A H 0.3150 0.3904 0.4437 0.022 Uiso 1 1 calc R . .
H32B H 0.5009 0.3693 0.5343 0.022 Uiso 1 1 calc R . .
O31A O 0.0674(3) 0.40081(14) 0.60433(11) 0.0299(3) Uani 1 1 d . . .
H31 H -0.0205 0.4369 0.6538 0.045 Uiso 1 1 calc R . .
O31B O 0.2497(2) 0.62819(13) 0.64550(10) 0.0238(3) Uani 1 1 d . . .
C42 C -0.7204(3) 0.39826(18) 1.20842(13) 0.0182(3) Uani 1 1 d . . .
C44 C -0.5363(3) 0.21210(19) 1.09930(14) 0.0210(4) Uani 1 1 d . . .
H44A H -0.3892 0.1899 1.1355 0.025 Uiso 1 1 calc R . .
H44B H -0.5274 0.1751 1.0214 0.025 Uiso 1 1 calc R . .
C45 C -0.7712(3) 0.14809(18) 1.13788(13) 0.0212(4) Uani 1 1 d . . .
H45A H -0.9016 0.1175 1.0802 0.025 Uiso 1 1 calc R . .
H45B H -0.7416 0.0640 1.1665 0.025 Uiso 1 1 calc R . .
N41 N -0.8318(3) 0.27267(16) 1.22157(11) 0.0211(3) Uani 1 1 d . . .
H41 H -0.9275 0.2665 1.2733 0.025 Uiso 1 1 calc R . .
N43 N -0.5639(3) 0.36760(15) 1.12953(11) 0.0199(3) Uani 1 1 d . . .
H43 H -0.4897 0.4324 1.1007 0.024 Uiso 1 1 calc R . .
O42 O -0.7538(2) 0.52470(13) 1.25851(10) 0.0234(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 0.0190(8) 0.0155(8) 0.0178(7) 0.0033(6) 0.0051(6) 0.0020(6)
C2 0.0167(8) 0.0168(8) 0.0213(8) 0.0033(6) 0.0074(6) 0.0016(6)
O1A 0.0264(7) 0.0147(6) 0.0268(6) 0.0015(5) 0.0127(5) 0.0001(5)
O1B 0.0259(7) 0.0172(6) 0.0315(7) 0.0031(5) 0.0169(5) 0.0010(5)
C22 0.0198(8) 0.0158(7) 0.0212(8) 0.0040(6) 0.0021(6) 0.0033(6)
C24 0.0213(8) 0.0185(8) 0.0238(8) 0.0041(6) 0.0070(6) 0.0006(6)
C25 0.0240(9) 0.0192(8) 0.0243(8) 0.0054(7) 0.0054(7) 0.0006(7)
N21 0.0280(8) 0.0151(7) 0.0372(9) -0.0006(6) 0.0134(7) 0.0006(6)
N23 0.0244(8) 0.0146(7) 0.0262(7) 0.0014(6) 0.0104(6) -0.0012(6)
O22 0.0239(6) 0.0194(6) 0.0267(7) 0.0033(5) 0.0102(5) 0.0033(5)
C31 0.0171(8) 0.0170(8) 0.0191(8) 0.0038(6) 0.0058(6) 0.0010(6)
C32 0.0185(8) 0.0156(7) 0.0201(8) 0.0017(6) 0.0082(6) 0.0013(6)
O31A 0.0324(7) 0.0187(6) 0.0339(7) -0.0018(5) 0.0215(6) -0.0051(5)
O31B 0.0239(6) 0.0168(6) 0.0275(7) -0.0006(5) 0.0135(5) 0.0003(5)
C42 0.0162(8) 0.0199(8) 0.0185(8) 0.0048(6) 0.0050(6) 0.0011(6)
C44 0.0212(8) 0.0180(8) 0.0236(8) 0.0037(6) 0.0086(6) 0.0027(6)
C45 0.0222(8) 0.0188(8) 0.0222(8) 0.0042(6) 0.0060(6) 0.0015(7)
N41 0.0218(7) 0.0191(7) 0.0222(7) 0.0048(6) 0.0104(6) -0.0004(6)
N43 0.0215(7) 0.0162(7) 0.0230(7) 0.0054(5) 0.0105(6) 0.0025(5)
O42 0.0237(7) 0.0187(6) 0.0267(7) 0.0025(5) 0.0124(5) 0.0021(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 O1B 1.224(2) . ?
C1 O1A 1.307(2) . ?
C1 C2 1.500(2) . ?
C2 C2 1.510(3) 2_567 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O1A H1 0.8400 . ?
C22 O22 1.248(2) . ?
C22 N21 1.340(2) . ?
C22 N23 1.353(2) . ?
C24 N23 1.456(2) . ?
C24 C25 1.539(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.458(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C31 O31B 1.2218(19) . ?
C31 O31A 1.309(2) . ?
C31 C32 1.502(2) . ?
C32 C32 1.511(3) 2_666 ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
O31A H31 0.8400 . ?
C42 O42 1.248(2) . ?
C42 N41 1.349(2) . ?
C42 N43 1.355(2) . ?
C44 N43 1.456(2) . ?
C44 C45 1.536(2) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 N41 1.463(2) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
N41 H41 0.8800 . ?
N43 H43 0.8800 . ?

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
O1B C1 O1A 123.33(14) . . ?
O1B C1 C2 124.02(15) . . ?
O1A C1 C2 112.65(13) . . ?
C1 C2 C2 113.23(17) . 2_567 ?
C1 C2 H2A 108.9 . . ?
C2 C2 H2A 108.9 2_567 . ?
C1 C2 H2B 108.9 . . ?
C2 C2 H2B 108.9 2_567 . ?
H2A C2 H2B 107.7 . . ?
C1 O1A H1 109.5 . . ?
O22 C22 N21 127.08(16) . . ?
O22 C22 N23 123.64(16) . . ?
N21 C22 N23 109.28(15) . . ?
N23 C24 C25 102.56(13) . . ?
N23 C24 H24A 111.3 . . ?
C25 C24 H24A 111.3 . . ?
N23 C24 H24B 111.3 . . ?
C25 C24 H24B 111.3 . . ?
H24A C24 H24B 109.2 . . ?
N21 C25 C24 102.31(14) . . ?
N21 C25 H25A 111.3 . . ?
C24 C25 H25A 111.3 . . ?
N21 C25 H25B 111.3 . . ?
C24 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
C22 N21 C25 112.17(14) . . ?
C22 N21 H21 123.9 . . ?
C25 N21 H21 123.9 . . ?
C22 N23 C24 111.24(14) . . ?
C22 N23 H23 124.4 . . ?
C24 N23 H23 124.4 . . ?
O31B C31 O31A 123.53(15) . . ?
O31B C31 C32 124.09(15) . . ?
O31A C31 C32 112.38(13) . . ?
C31 C32 C32 113.14(17) . 2_666 ?
C31 C32 H32A 109.0 . . ?
C32 C32 H32A 109.0 2_666 . ?
C31 C32 H32B 109.0 . . ?
C32 C32 H32B 109.0 2_666 . ?
H32A C32 H32B 107.8 . . ?
C31 O31A H31 109.5 . . ?
O42 C42 N41 126.84(15) . . ?
O42 C42 N43 123.71(16) . . ?
N41 C42 N43 109.44(14) . . ?
N43 C44 C45 101.78(13) . . ?
N43 C44 H44A 111.4 . . ?
C45 C44 H44A 111.4 . . ?
N43 C44 H44B 111.4 . . ?
C45 C44 H44B 111.4 . . ?
H44A C44 H44B 109.3 . . ?
N41 C45 C44 101.42(13) . . ?
N41 C45 H45A 111.5 . . ?
C44 C45 H45A 111.5 . . ?
N41 C45 H45B 111.5 . . ?
C44 C45 H45B 111.5 . . ?
H45A C45 H45B 109.3 . . ?
C42 N41 C45 110.55(14) . . ?
C42 N41 H41 124.7 . . ?
C45 N41 H41 124.7 . . ?
C42 N43 C44 110.28(14) . . ?
C42 N43 H43 124.9 . . ?
C44 N43 H43 124.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1A H1 O22 0.84 1.71 2.5293(17) 165.6 2_656
N21 H21 O1B 0.88 2.26 3.047(2) 148.8 2_656
O31A H31 O42 0.84 1.72 2.5418(17) 166.6 2_467
N41 H41 O31B 0.88 2.28 3.0023(19) 139.9 2_467
N23 H23 O31B 0.88 2.13 2.914(2) 147.3 2_666
N43 H43 O1B 0.88 2.12 2.879(2) 144.0 2_567

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        26.64
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.058

# Attachment '5.cif'

data_07skc0011p21c
_database_code_depnum_ccdc_archive 'CCDC 717669'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H22 N4 O6'
_chemical_formula_weight         318.34

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   P21/c

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

_cell_length_a                   7.7814(3)
_cell_length_b                   22.3584(11)
_cell_length_c                   9.1957(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.329(3)
_cell_angle_gamma                90.00
_cell_volume                     1556.77(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3364
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9859
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14674
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_sigmaI/netI    0.0856
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3521
_reflns_number_gt                2194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0127P)²+4.5713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3521
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1552
_refine_ls_R_factor_gt           0.0934
_refine_ls_wR_factor_ref         0.1880
_refine_ls_wR_factor_gt          0.1574
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.003

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 0.9036(5) -0.02891(17) 1.2022(4) 0.0233(8) Uani 1 1 d . . .
C2 C 0.8931(5) 0.03736(16) 1.1668(4) 0.0225(8) Uani 1 1 d . . .
H2A H 1.0122 0.0520 1.1633 0.027 Uiso 1 1 calc R . .
H2B H 0.8556 0.0590 1.2482 0.027 Uiso 1 1 calc R . .
C3 C 0.7651(5) 0.05173(16) 1.0190(4) 0.0219(8) Uani 1 1 d . . .
H3A H 0.6452 0.0385 1.0238 0.026 Uiso 1 1 calc R . .
H3B H 0.8001 0.0290 0.9380 0.026 Uiso 1 1 calc R . .
C4 C 0.7598(5) 0.11830(15) 0.9811(4) 0.0191(8) Uani 1 1 d . . .
H4A H 0.7294 0.1413 1.0636 0.023 Uiso 1 1 calc R . .
H4B H 0.8782 0.1313 0.9713 0.023 Uiso 1 1 calc R . .
C5 C 0.6252(5) 0.13175(16) 0.8364(4) 0.0238(9) Uani 1 1 d . . .
H5A H 0.6606 0.1107 0.7533 0.029 Uiso 1 1 calc R . .
H5B H 0.5089 0.1158 0.8440 0.029 Uiso 1 1 calc R . .
C6 C 0.6066(5) 0.19715(17) 0.8003(4) 0.0220(8) Uani 1 1 d . . .
O1A O 1.0315(4) -0.04297(12) 1.3160(3) 0.0333(7) Uani 1 1 d . . .
H1 H 1.0327 -0.0802 1.3288 0.050 Uiso 1 1 calc R . .
O1B O 0.8027(4) -0.06541(11) 1.1299(3) 0.0321(7) Uani 1 1 d . . .
O6A O 0.6751(3) 0.23670(11) 0.8838(3) 0.0264(7) Uani 1 1 d . . .
O6B O 0.5035(4) 0.20743(12) 0.6662(3) 0.0293(7) Uani 1 1 d . . .
H6 H 0.4930 0.2445 0.6517 0.044 Uiso 1 1 calc R . .
C22 C 0.4539(5) 0.36287(16) 0.7029(4) 0.0227(8) Uani 1 1 d . . .
C24 C 0.5462(6) 0.41567(17) 0.9224(5) 0.0333(10) Uani 1 1 d . . .
H24A H 0.6609 0.4325 0.9762 0.040 Uiso 1 1 calc R . .
H24B H 0.4736 0.4065 0.9949 0.040 Uiso 1 1 calc R . .
C25 C 0.4493(6) 0.45812(17) 0.7992(5) 0.0304(10) Uani 1 1 d . . .
H25A H 0.3595 0.4823 0.8333 0.036 Uiso 1 1 calc R . .
H25B H 0.5328 0.4852 0.7650 0.036 Uiso 1 1 calc R . .
N21 N 0.3677(4) 0.41618(14) 0.6821(4) 0.0276(8) Uani 1 1 d . . .
H21 H 0.2760 0.4242 0.6088 0.033 Uiso 1 1 calc R . .
N23 N 0.5702(4) 0.36318(14) 0.8357(4) 0.0269(8) Uani 1 1 d . . .
H23 H 0.6503 0.3353 0.8664 0.032 Uiso 1 1 calc R . .
O22 O 0.4255(3) 0.32078(11) 0.6112(3) 0.0237(6) Uani 1 1 d . . .
C32 C 0.0063(5) 0.69651(17) 0.8064(4) 0.0231(8) Uani 1 1 d . . .
C34 C -0.0361(5) 0.79529(17) 0.7328(5) 0.0268(9) Uani 1 1 d . . .
H34A H 0.0504 0.8112 0.6788 0.032 Uiso 1 1 calc R . .
H34B H -0.0913 0.8290 0.7750 0.032 Uiso 1 1 calc R . .
C35 C -0.1757(5) 0.75594(16) 0.6307(5) 0.0244(9) Uani 1 1 d . . .
H35A H -0.2945 0.7626 0.6494 0.029 Uiso 1 1 calc R . .
H35B H -0.1797 0.7635 0.5239 0.029 Uiso 1 1 calc R . .
N31 N -0.1118(4) 0.69607(14) 0.6746(4) 0.0280(8) Uani 1 1 d . . .
H31 H -0.1461 0.6637 0.6215 0.034 Uiso 1 1 calc R . .
N33 N 0.0458(4) 0.75303(13) 0.8483(4) 0.0256(8) Uani 1 1 d . . .
H33 H 0.1132 0.7634 0.9352 0.031 Uiso 1 1 calc R . .
O32 O 0.0728(4) 0.65166(11) 0.8816(3) 0.0307(7) 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 0.024(2) 0.021(2) 0.022(2) 0.0011(16) 0.0008(16) 0.0001(16)
C2 0.029(2) 0.0144(18) 0.022(2) 0.0029(15) 0.0002(16) 0.0024(15)
C3 0.024(2) 0.0173(19) 0.023(2) 0.0021(15) 0.0019(15) -0.0003(15)
C4 0.0183(18) 0.0153(18) 0.022(2) -0.0003(14) 0.0011(15) 0.0007(14)
C5 0.026(2) 0.0147(18) 0.027(2) -0.0003(16) -0.0015(16) -0.0004(15)
C6 0.0199(19) 0.025(2) 0.020(2) 0.0021(16) 0.0021(15) 0.0032(16)
O1A 0.0394(17) 0.0165(14) 0.0323(18) 0.0032(12) -0.0157(13) -0.0002(12)
O1B 0.0372(16) 0.0168(14) 0.0330(17) 0.0047(12) -0.0108(13) -0.0058(12)
O6A 0.0296(15) 0.0166(14) 0.0276(16) -0.0008(11) -0.0044(12) 0.0009(11)
O6B 0.0379(17) 0.0176(14) 0.0267(16) 0.0005(12) -0.0042(12) 0.0030(12)
C22 0.023(2) 0.0179(19) 0.026(2) 0.0003(16) 0.0019(16) 0.0001(15)
C24 0.047(3) 0.022(2) 0.026(2) 0.0016(18) -0.0027(19) 0.0092(19)
C25 0.036(2) 0.022(2) 0.030(2) -0.0046(17) 0.0000(18) 0.0033(17)
N21 0.0280(18) 0.0217(17) 0.026(2) 0.0007(14) -0.0082(14) 0.0036(14)
N23 0.0303(18) 0.0201(17) 0.0248(19) -0.0024(14) -0.0053(14) 0.0094(14)
O22 0.0270(14) 0.0177(13) 0.0243(16) 0.0005(11) 0.0016(11) 0.0010(11)
C32 0.0232(19) 0.0202(19) 0.025(2) -0.0047(16) 0.0037(16) -0.0007(15)
C34 0.029(2) 0.0180(19) 0.029(2) -0.0022(17) -0.0027(17) -0.0008(16)
C35 0.024(2) 0.0197(19) 0.028(2) -0.0024(16) 0.0029(16) 0.0008(15)
N31 0.0306(18) 0.0183(16) 0.029(2) -0.0079(14) -0.0056(14) -0.0007(14)
N33 0.0350(19) 0.0167(16) 0.0205(18) -0.0045(13) -0.0027(14) -0.0032(14)
O32 0.0367(16) 0.0167(14) 0.0322(18) -0.0052(12) -0.0057(13) 0.0023(12)

_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 O1B 1.218(4) . ?
C1 O1A 1.305(4) . ?
C1 C2 1.515(5) . ?
C2 C3 1.523(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.527(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.521(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.499(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O6A 1.211(4) . ?
C6 O6B 1.328(4) . ?
O1A H1 0.8400 . ?
O6B H6 0.8400 . ?
C22 O22 1.249(4) . ?
C22 N23 1.342(5) . ?
C22 N21 1.360(5) . ?
C24 N23 1.454(5) . ?
C24 C25 1.536(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.458(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C32 O32 1.260(5) . ?
C32 N33 1.336(5) . ?
C32 N31 1.342(5) . ?
C34 N33 1.454(5) . ?
C34 C35 1.538(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 N31 1.452(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
N31 H31 0.8800 . ?
N33 H33 0.8800 . ?

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
O1B C1 O1A 123.5(3) . . ?
O1B C1 C2 122.8(3) . . ?
O1A C1 C2 113.6(3) . . ?
C1 C2 C3 112.9(3) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 112.8(3) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.7(3) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 113.5(3) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O6A C6 O6B 123.1(3) . . ?
O6A C6 C5 124.5(3) . . ?
O6B C6 C5 112.4(3) . . ?
C1 O1A H1 109.5 . . ?
C6 O6B H6 109.5 . . ?
O22 C22 N23 126.6(3) . . ?
O22 C22 N21 124.1(3) . . ?
N23 C22 N21 109.3(3) . . ?
N23 C24 C25 101.4(3) . . ?
N23 C24 H24A 111.5 . . ?
C25 C24 H24A 111.5 . . ?
N23 C24 H24B 111.5 . . ?
C25 C24 H24B 111.5 . . ?
H24A C24 H24B 109.3 . . ?
N21 C25 C24 101.7(3) . . ?
N21 C25 H25A 111.4 . . ?
C24 C25 H25A 111.4 . . ?
N21 C25 H25B 111.4 . . ?
C24 C25 H25B 111.4 . . ?
H25A C25 H25B 109.3 . . ?
C22 N21 C25 110.1(3) . . ?
C22 N21 H21 125.0 . . ?
C25 N21 H21 125.0 . . ?
C22 N23 C24 111.0(3) . . ?
C22 N23 H23 124.5 . . ?
C24 N23 H23 124.5 . . ?
O32 C32 N33 123.8(3) . . ?
O32 C32 N31 126.8(3) . . ?
N33 C32 N31 109.3(3) . . ?
N33 C34 C35 101.7(3) . . ?
N33 C34 H34A 111.4 . . ?
C35 C34 H34A 111.4 . . ?
N33 C34 H34B 111.4 . . ?
C35 C34 H34B 111.4 . . ?
H34A C34 H34B 109.3 . . ?
N31 C35 C34 102.1(3) . . ?
N31 C35 H35A 111.4 . . ?
C34 C35 H35A 111.4 . . ?
N31 C35 H35B 111.4 . . ?
C34 C35 H35B 111.4 . . ?
H35A C35 H35B 109.2 . . ?
C32 N31 C35 111.3(3) . . ?
C32 N31 H31 124.3 . . ?
C35 N31 H31 124.3 . . ?
C32 N33 C34 111.8(3) . . ?
C32 N33 H33 124.1 . . ?
C34 N33 H33 124.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6B H6 O22 0.84 1.80 2.628(4) 168.9 .
N23 H23 O6A 0.88 2.22 2.948(4) 140.4 .
O1A H1 O32 0.84 1.68 2.507(4) 168.2 4_666
N21 H21 O1B 0.88 2.15 2.900(4) 142.6 2_656
N31 H31 O1B 0.88 2.24 3.003(4) 145.4 4_465
N33 H33 O6A 0.88 2.05 2.894(4) 159.1 3_667

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.083

# Attachment '6.cif'

data_06skc0046c2c
_database_code_depnum_ccdc_archive 'CCDC 717670'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
6
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H22 N6 O7'
_chemical_formula_weight         362.36

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   C2/c

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

_cell_length_a                   16.6403(10)
_cell_length_b                   14.4382(5)
_cell_length_c                   7.6872(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.299(2)
_cell_angle_gamma                90.00
_cell_volume                     1641.20(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1896
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9785
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10932
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1868
_reflns_number_gt                1411
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Non-merohedral twin matrix (1 0 2, 0 -1 0, 0 0 -1) gave BASF parameter
0.1347.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0707P)²+0.8687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1868
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C2 C 0.0000 0.25717(19) 0.7500 0.0229(7) Uani 1 2 d S . .
H2A H -0.0189 0.2978 0.6340 0.028 Uiso 0.50 1 calc PR . .
H2B H 0.0189 0.2978 0.8660 0.028 Uiso 0.50 1 calc PR . .
C1 C 0.08090(14) 0.20172(14) 0.7720(3) 0.0227(5) Uani 1 1 d . . .
O1A O 0.09902(11) 0.12454(10) 0.8410(3) 0.0314(4) Uani 1 1 d . . .
O1B O 0.13161(11) 0.24960(10) 0.7127(3) 0.0286(4) Uani 1 1 d . . .
H1 H 0.1792 0.2200 0.7386 0.043 Uiso 1 1 calc R . .
C22 C 0.30067(14) 0.09879(14) 0.7980(3) 0.0237(5) Uani 1 1 d . . .
C24 C 0.27549(15) -0.05963(14) 0.8004(3) 0.0254(5) Uani 1 1 d . . .
H24A H 0.2379 -0.1009 0.6899 0.031 Uiso 1 1 calc R . .
H24B H 0.2812 -0.0868 0.9238 0.031 Uiso 1 1 calc R . .
C25 C 0.36896(15) -0.04279(14) 0.8104(3) 0.0250(5) Uani 1 1 d . . .
H25A H 0.4172 -0.0754 0.9235 0.030 Uiso 1 1 calc R . .
H25B H 0.3701 -0.0634 0.6888 0.030 Uiso 1 1 calc R . .
N21 N 0.37930(12) 0.05759(12) 0.8336(3) 0.0255(5) Uani 1 1 d . . .
H21 H 0.4304 0.0873 0.8667 0.031 Uiso 1 1 calc R . .
N23 N 0.23769(12) 0.03373(12) 0.7703(3) 0.0278(5) Uani 1 1 d . . .
H23 H 0.1808 0.0461 0.7381 0.033 Uiso 1 1 calc R . .
O22 O 0.28866(10) 0.18457(10) 0.7921(3) 0.0301(4) Uani 1 1 d . . .
C32 C 0.5000 0.2475(2) 0.7500 0.0219(6) Uani 1 2 d S . .
C35 C 0.45317(16) 0.39936(15) 0.7483(4) 0.0297(6) Uani 1 1 d . . .
H35A H 0.4532 0.4387 0.8539 0.036 Uiso 1 1 calc R . .
H35B H 0.4052 0.4209 0.6206 0.036 Uiso 1 1 calc R . .
N31 N 0.44173(13) 0.30174(12) 0.7809(3) 0.0256(5) Uani 1 1 d . . .
H31 H 0.4017 0.2808 0.8163 0.031 Uiso 1 1 calc R . .
O32 O 0.5000 0.16140(14) 0.7500 0.0256(5) Uani 1 2 d S . .

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
C2 0.0232(16) 0.0175(14) 0.0293(17) 0.000 0.0131(14) 0.000
C1 0.0206(11) 0.0219(11) 0.0259(11) -0.0012(8) 0.0110(9) -0.0009(8)
O1A 0.0295(9) 0.0228(8) 0.0492(11) 0.0094(7) 0.0243(8) 0.0058(6)
O1B 0.0214(8) 0.0229(8) 0.0464(10) 0.0058(7) 0.0198(8) 0.0027(6)
C22 0.0218(11) 0.0226(11) 0.0276(12) 0.0005(8) 0.0121(10) 0.0004(8)
C24 0.0256(12) 0.0199(10) 0.0312(12) -0.0008(9) 0.0134(10) -0.0016(8)
C25 0.0259(11) 0.0210(11) 0.0286(12) 0.0004(8) 0.0130(10) 0.0029(8)
N21 0.0207(10) 0.0203(9) 0.0380(12) -0.0017(7) 0.0155(9) -0.0008(7)
N23 0.0189(9) 0.0210(9) 0.0440(12) 0.0005(8) 0.0149(9) -0.0007(7)
O22 0.0248(8) 0.0197(8) 0.0500(11) 0.0004(7) 0.0208(8) 0.0006(6)
C32 0.0205(15) 0.0220(15) 0.0240(16) 0.000 0.0109(14) 0.000
C35 0.0321(13) 0.0181(10) 0.0399(14) 0.0004(9) 0.0174(11) 0.0031(9)
N31 0.0249(10) 0.0221(10) 0.0355(11) 0.0023(8) 0.0188(9) 0.0017(7)
O32 0.0252(11) 0.0198(11) 0.0372(13) 0.000 0.0190(11) 0.000

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C2 C1 1.508(3) . ?
C2 C1 1.508(3) 2_556 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 O1A 1.211(3) . ?
C1 O1B 1.323(3) . ?
O1B H1 0.8400 . ?
C22 O22 1.252(3) . ?
C22 N21 1.346(3) . ?
C22 N23 1.350(3) . ?
C24 N23 1.460(3) . ?
C24 C25 1.541(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.461(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?
C32 O32 1.244(3) . ?
C32 N31 1.349(2) 2_656 ?
C32 N31 1.349(2) . ?
C35 N31 1.459(3) . ?
C35 C35 1.547(5) 2_656 ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
N31 H31 0.8800 . ?

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
C1 C2 C1 115.8(2) . 2_556 ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2A 108.3 2_556 . ?
C1 C2 H2B 108.3 . . ?
C1 C2 H2B 108.3 2_556 . ?
H2A C2 H2B 107.4 . . ?
O1A C1 O1B 124.16(19) . . ?
O1A C1 C2 124.60(19) . . ?
O1B C1 C2 111.20(17) . . ?
C1 O1B H1 109.5 . . ?
O22 C22 N21 124.65(19) . . ?
O22 C22 N23 125.69(19) . . ?
N21 C22 N23 109.67(18) . . ?
N23 C24 C25 102.36(17) . . ?
N23 C24 H24A 111.3 . . ?
C25 C24 H24A 111.3 . . ?
N23 C24 H24B 111.3 . . ?
C25 C24 H24B 111.3 . . ?
H24A C24 H24B 109.2 . . ?
N21 C25 C24 102.84(16) . . ?
N21 C25 H25A 111.2 . . ?
C24 C25 H25A 111.2 . . ?
N21 C25 H25B 111.2 . . ?
C24 C25 H25B 111.2 . . ?
H25A C25 H25B 109.1 . . ?
C22 N21 C25 111.38(17) . . ?
C22 N21 H21 124.3 . . ?
C25 N21 H21 124.3 . . ?
C22 N23 C24 111.75(17) . . ?
C22 N23 H23 124.1 . . ?
C24 N23 H23 124.1 . . ?
O32 C32 N31 125.46(12) . 2_656 ?
O32 C32 N31 125.46(12) . . ?
N31 C32 N31 109.1(2) 2_656 . ?
N31 C35 C35 101.93(12) . 2_656 ?
N31 C35 H35A 111.4 . . ?
C35 C35 H35A 111.4 2_656 . ?
N31 C35 H35B 111.4 . . ?
C35 C35 H35B 111.4 2_656 . ?
H35A C35 H35B 109.2 . . ?
C32 N31 C35 111.68(18) . . ?
C32 N31 H31 124.2 . . ?
C35 N31 H31 124.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1B H1 O22 0.84 1.75 2.573(2) 166.3 .
N21 H21 O32 0.88 2.06 2.807(2) 142.1 .
N23 H23 O1A 0.88 2.18 2.914(2) 140.7 .
N31 H31 O22 0.88 2.28 3.092(2) 153.9 .

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.057

# Attachment '7.cif'

data_07skc0005cc
_database_code_depnum_ccdc_archive 'CCDC 717671'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
7
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H14 N2 O5'
_chemical_formula_weight         218.21

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc

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                   5.3007(4)
_cell_length_b                   19.374(2)
_cell_length_c                   10.0780(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.012(6)
_cell_angle_gamma                90.00
_cell_volume                     1032.43(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    20712
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9713
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8779
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         27.45
_reflns_number_total             1186
_reflns_number_gt                1005
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

MERG 4 was used as there are no heavy atoms present in the structure
(therefore the Flack parameter is meaningless).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.3364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_number_reflns         1186
_refine_ls_number_parameters     138
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.069
_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 -0.4059(6) 0.40824(15) 1.0002(3) 0.0252(7) Uani 1 1 d . . .
C2 C -0.3910(6) 0.44225(16) 0.8670(3) 0.0240(6) Uani 1 1 d . . .
H2A H -0.3661 0.4925 0.8798 0.029 Uiso 1 1 calc R . .
H2B H -0.5526 0.4352 0.8133 0.029 Uiso 1 1 calc R . .
C3 C -0.1740(6) 0.41304(17) 0.7918(3) 0.0264(6) Uani 1 1 d . . .
H3A H -0.0135 0.4190 0.8470 0.032 Uiso 1 1 calc R . .
H3B H -0.2013 0.3629 0.7780 0.032 Uiso 1 1 calc R . .
C4 C -0.1502(6) 0.44747(16) 0.6578(3) 0.0256(6) Uani 1 1 d . . .
H4A H -0.3158 0.4459 0.6060 0.031 Uiso 1 1 calc R . .
H4B H -0.1035 0.4965 0.6719 0.031 Uiso 1 1 calc R . .
C5 C 0.0457(5) 0.41278(15) 0.5797(3) 0.0226(6) Uani 1 1 d . . .
O1A O -0.2623(4) 0.36267(13) 1.0400(2) 0.0368(6) Uani 1 1 d . . .
O1B O -0.5930(4) 0.43159(12) 1.0691(2) 0.0291(5) Uani 1 1 d . . .
H1 H -0.5933 0.4102 1.1416 0.044 Uiso 1 1 calc R . .
O5A O 0.1942(4) 0.36998(13) 0.6275(2) 0.0337(6) Uani 1 1 d . . .
O5B O 0.0410(4) 0.43294(12) 0.4536(2) 0.0290(5) Uani 1 1 d . . .
H5 H 0.1670 0.4167 0.4182 0.044 Uiso 1 1 calc R . .
C22 C -0.4488(5) 0.33005(15) 0.3590(3) 0.0248(6) Uani 1 1 d . . .
C24 C -0.1278(6) 0.24876(17) 0.3686(3) 0.0275(7) Uani 1 1 d . . .
H24A H 0.0448 0.2680 0.3835 0.033 Uiso 1 1 calc R . .
H24B H -0.1177 0.2023 0.3282 0.033 Uiso 1 1 calc R . .
C25 C -0.2635(6) 0.24629(16) 0.4988(3) 0.0285(7) Uani 1 1 d . . .
H25A H -0.3640 0.2035 0.5049 0.034 Uiso 1 1 calc R . .
H25B H -0.1418 0.2498 0.5776 0.034 Uiso 1 1 calc R . .
N21 N -0.4268(5) 0.30739(14) 0.4856(3) 0.0303(6) Uani 1 1 d . . .
H21 H -0.5007 0.3267 0.5518 0.036 Uiso 1 1 calc R . .
N23 N -0.2917(5) 0.29463(14) 0.2855(3) 0.0299(6) Uani 1 1 d . . .
H23 H -0.2877 0.2985 0.1986 0.036 Uiso 1 1 calc R . .
O22 O -0.5974(4) 0.37721(11) 0.3150(2) 0.0287(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 0.0240(15) 0.0279(16) 0.0236(15) -0.0027(13) 0.0010(12) -0.0024(13)
C2 0.0267(16) 0.0262(15) 0.0191(14) -0.0001(11) 0.0017(12) -0.0003(12)
C3 0.0265(15) 0.0286(15) 0.0245(15) 0.0023(12) 0.0035(11) 0.0035(13)
C4 0.0262(16) 0.0277(15) 0.0233(14) 0.0006(12) 0.0040(12) 0.0027(13)
C5 0.0229(15) 0.0247(15) 0.0201(14) 0.0012(11) 0.0010(11) 0.0001(12)
O1A 0.0414(14) 0.0426(14) 0.0274(12) 0.0083(10) 0.0099(10) 0.0150(11)
O1B 0.0292(12) 0.0331(12) 0.0256(11) 0.0058(9) 0.0074(9) 0.0041(9)
O5A 0.0329(13) 0.0458(14) 0.0228(10) 0.0050(10) 0.0043(9) 0.0130(10)
O5B 0.0297(13) 0.0360(12) 0.0218(11) 0.0043(9) 0.0051(8) 0.0060(10)
C22 0.0254(15) 0.0254(15) 0.0236(15) -0.0007(12) 0.0012(11) -0.0006(12)
C24 0.0262(15) 0.0299(16) 0.0262(14) 0.0021(13) 0.0014(12) 0.0044(13)
C25 0.0282(16) 0.0285(16) 0.0286(15) 0.0032(13) 0.0004(12) 0.0048(14)
N21 0.0355(15) 0.0311(14) 0.0245(14) 0.0017(11) 0.0036(11) 0.0078(12)
N23 0.0347(15) 0.0322(14) 0.0229(14) 0.0002(10) 0.0035(11) 0.0087(12)
O22 0.0295(11) 0.0331(12) 0.0239(11) 0.0037(9) 0.0042(8) 0.0069(10)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 O1A 1.216(4) . ?
C1 O1B 1.330(4) . ?
C1 C2 1.502(4) . ?
C2 C3 1.529(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.519(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.505(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O5A 1.219(4) . ?
C5 O5B 1.328(4) . ?
O1B H1 0.8400 . ?
O5B H5 0.8400 . ?
C22 O22 1.266(4) . ?
C22 N23 1.342(4) . ?
C22 N21 1.346(4) . ?
C24 N23 1.464(4) . ?
C24 C25 1.541(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.467(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?

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
O1A C1 O1B 123.2(3) . . ?
O1A C1 C2 122.9(3) . . ?
O1B C1 C2 113.9(3) . . ?
C1 C2 C3 111.6(2) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 113.0(3) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.9(2) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O5A C5 O5B 123.1(3) . . ?
O5A C5 C4 123.2(3) . . ?
O5B C5 C4 113.7(2) . . ?
C1 O1B H1 109.5 . . ?
C5 O5B H5 109.5 . . ?
O22 C22 N23 124.8(3) . . ?
O22 C22 N21 125.3(3) . . ?
N23 C22 N21 109.9(3) . . ?
N23 C24 C25 102.3(2) . . ?
N23 C24 H24A 111.3 . . ?
C25 C24 H24A 111.3 . . ?
N23 C24 H24B 111.3 . . ?
C25 C24 H24B 111.3 . . ?
H24A C24 H24B 109.2 . . ?
N21 C25 C24 101.9(2) . . ?
N21 C25 H25A 111.4 . . ?
C24 C25 H25A 111.4 . . ?
N21 C25 H25B 111.4 . . ?
C24 C25 H25B 111.4 . . ?
H25A C25 H25B 109.3 . . ?
C22 N21 C25 111.1(3) . . ?
C22 N21 H21 124.4 . . ?
C25 N21 H21 124.4 . . ?
C22 N23 C24 111.1(3) . . ?
C22 N23 H23 124.4 . . ?
C24 N23 H23 124.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1B H1 O22 0.84 1.86 2.694(3) 170.5 1_556
O5B H5 O22 0.84 1.85 2.676(3) 169.6 1_655
N21 H21 O5A 0.88 2.02 2.820(3) 150.9 1_455
N23 H23 O1A 0.88 2.04 2.817(3) 147.1 1_554

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052

# Attachment '8.cif'

data_07skc0003cmcm
_database_code_depnum_ccdc_archive 'CCDC 717672'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
8
;
_chemical_name_common            8
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H18 N2 O5'
_chemical_formula_weight         246.26

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'
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   Cmcm

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

_cell_length_a                   6.8156(6)
_cell_length_b                   12.7537(12)
_cell_length_c                   14.1899(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1233.44(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    815
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9842
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4539
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         27.48
_reflns_number_total             800
_reflns_number_gt                578
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0213P)²+2.1920P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         800
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.171
_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 0.0000 0.3041(2) 0.48515(19) 0.0262(6) Uani 1 2 d S . .
C2 C 0.0000 0.3750(2) 0.56975(18) 0.0260(7) Uani 1 2 d S . .
H2A H -0.1174 0.4206 0.5675 0.031 Uiso 0.50 1 calc PR . .
H2B H 0.1174 0.4206 0.5675 0.031 Uiso 0.50 1 calc PR . .
C3 C 0.0000 0.3141(2) 0.66175(17) 0.0238(6) Uani 1 2 d S . .
H3A H 0.1172 0.2683 0.6633 0.029 Uiso 0.50 1 calc PR . .
H3B H -0.1172 0.2683 0.6633 0.029 Uiso 0.50 1 calc PR . .
C4 C 0.0000 0.3831(3) 0.7500 0.0249(9) Uani 1 4 d S . .
H4A H -0.1177 0.4286 0.7500 0.030 Uiso 0.50 2 calc SPR . .
H4B H 0.1177 0.4286 0.7500 0.030 Uiso 0.50 2 calc SPR . .
O1B O 0.0000 0.20910(16) 0.48986(14) 0.0362(6) Uani 1 2 d S . .
O1A O 0.0000 0.35654(16) 0.40422(13) 0.0322(6) Uani 1 2 d S . .
H1 H 0.0000 0.3139 0.3591 0.048 Uiso 1 2 calc SR . .
C22 C 0.0000 0.1399(3) 0.2500 0.0249(9) Uani 1 4 d S . .
C25 C 0.0000 -0.0315(2) 0.3045(2) 0.0339(7) Uani 1 2 d S . .
H25A H -0.1183 -0.0667 0.3297 0.041 Uiso 0.50 1 calc PR . .
H25B H 0.1183 -0.0667 0.3297 0.041 Uiso 0.50 1 calc PR . .
N21 N 0.0000 0.07981(19) 0.32741(16) 0.0289(6) Uani 1 2 d S . .
H21 H 0.0000 0.1046 0.3853 0.035 Uiso 1 2 calc SR . .
O22 O 0.0000 0.2392(2) 0.2500 0.0262(7) Uani 1 4 d S . .

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 0.0287(16) 0.0272(15) 0.0225(14) 0.0011(12) 0.000 0.000
C2 0.0313(16) 0.0243(15) 0.0223(13) 0.0013(11) 0.000 0.000
C3 0.0304(15) 0.0217(14) 0.0192(13) 0.0011(11) 0.000 0.000
C4 0.029(2) 0.025(2) 0.0209(18) 0.000 0.000 0.000
O1B 0.0610(16) 0.0236(11) 0.0239(11) -0.0005(8) 0.000 0.000
O1A 0.0532(14) 0.0247(11) 0.0188(10) -0.0005(8) 0.000 0.000
C22 0.028(2) 0.021(2) 0.026(2) 0.000 0.000 0.000
C25 0.046(2) 0.0222(15) 0.0336(17) 0.0006(13) 0.000 0.000
N21 0.0404(16) 0.0228(13) 0.0235(12) -0.0001(10) 0.000 0.000
O22 0.0375(18) 0.0209(15) 0.0202(13) 0.000 0.000 0.000

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 O1B 1.213(3) . ?
C1 O1A 1.329(3) . ?
C1 C2 1.503(4) . ?
C2 C3 1.519(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C3 1.530(3) 10_557 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O1A H1 0.8400 . ?
C22 O22 1.267(5) . ?
C22 N21 1.339(3) 10_556 ?
C22 N21 1.339(3) . ?
C25 N21 1.456(4) . ?
C25 C25 1.546(6) 10_556 ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?

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
O1B C1 O1A 123.4(3) . . ?
O1B C1 C2 123.8(2) . . ?
O1A C1 C2 112.8(2) . . ?
C1 C2 C3 112.2(2) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 114.1(2) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C3 109.8(3) . 10_557 ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 10_557 . ?
C3 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 10_557 . ?
H4A C4 H4B 108.2 . . ?
C1 O1A H1 109.5 . . ?
O22 C22 N21 124.90(17) . 10_556 ?
O22 C22 N21 124.90(17) . . ?
N21 C22 N21 110.2(3) 10_556 . ?
N21 C25 C25 102.93(15) . 10_556 ?
N21 C25 H25A 111.2 . . ?
C25 C25 H25A 111.2 10_556 . ?
N21 C25 H25B 111.2 . . ?
C25 C25 H25B 111.2 10_556 . ?
H25A C25 H25B 109.1 . . ?
C22 N21 C25 112.0(2) . . ?
C22 N21 H21 124.0 . . ?
C25 N21 H21 124.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1A H1 O22 0.84 1.82 2.651(2) 171.3 .
N21 H21 O1B 0.88 1.99 2.834(3) 159.2 .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.058


# Attachment '9.cif'

data_ssg0307
_database_code_depnum_ccdc_archive 'CCDC 717673'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
9
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H12 N2 O7'
_chemical_formula_weight         236.19

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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                   5.3880(13)
_cell_length_b                   9.921(3)
_cell_length_c                   18.265(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     976.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    969
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      29.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.6895
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        5
_diffrn_reflns_number            8329
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         26.59
_reflns_number_total             1290
_reflns_number_gt                1245
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0518P)²+0.2244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_number_reflns         1290
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 1.1160(3) 0.60651(18) -0.05341(9) 0.0173(4) Uani 1 1 d . . .
C2 C 1.1370(3) 0.52683(18) 0.01826(9) 0.0167(4) Uani 1 1 d . . .
H2 H 1.1056 0.5913 0.0593 0.020 Uiso 1 1 calc R . .
C3 C 1.4075(4) 0.48047(18) 0.02432(9) 0.0176(4) Uani 1 1 d . . .
H3 H 1.5194 0.5605 0.0287 0.021 Uiso 1 1 calc R . .
C4 C 1.4361(3) 0.39043(18) 0.09143(9) 0.0180(4) Uani 1 1 d . . .
O1A O 1.2387(3) 0.70661(13) -0.06446(7) 0.0235(3) Uani 1 1 d . . .
O1B O 0.9569(3) 0.55301(13) -0.10011(7) 0.0228(3) Uani 1 1 d . . .
H1 H 0.9611 0.5961 -0.1397 0.052(8) Uiso 1 1 calc R . .
O2 O 0.9673(2) 0.42009(12) 0.02580(7) 0.0189(3) Uani 1 1 d . . .
H2O H 1.0068 0.3573 -0.0028 0.028 Uiso 1 1 calc R . .
O3 O 1.4626(2) 0.40865(15) -0.04033(7) 0.0219(3) Uani 1 1 d . . .
H3O H 1.6172 0.4055 -0.0462 0.033 Uiso 1 1 calc R . .
O4A O 1.4162(3) 0.45956(13) 0.15306(7) 0.0227(3) Uani 1 1 d . . .
H4 H 1.4485 0.4090 0.1887 0.036(7) Uiso 1 1 calc R . .
O4B O 1.4731(3) 0.27019(12) 0.08848(7) 0.0221(3) Uani 1 1 d . . .
C22 C 0.7533(3) 0.24990(18) 0.26385(9) 0.0184(3) Uani 1 1 d . . .
C24 C 1.0941(4) 0.11550(19) 0.29050(10) 0.0230(4) Uani 1 1 d . . .
H24A H 1.0601 0.0342 0.3203 0.028 Uiso 1 1 calc R . .
H24B H 1.2722 0.1390 0.2945 0.028 Uiso 1 1 calc R . .
C25 C 1.0165(4) 0.0951(2) 0.21039(11) 0.0316(5) Uani 1 1 d . . .
H25A H 1.1395 0.1349 0.1764 0.038 Uiso 1 1 calc R . .
H25B H 0.9957 -0.0017 0.1988 0.038 Uiso 1 1 calc R . .
N21 N 0.7804(3) 0.16654(17) 0.20687(8) 0.0251(4) Uani 1 1 d . . .
H21 H 0.6700 0.1561 0.1718 0.073(11) Uiso 1 1 calc R . .
N23 N 0.9358(3) 0.22816(16) 0.31232(8) 0.0244(4) Uani 1 1 d . . .
H23 H 0.9577 0.2759 0.3524 0.039(7) Uiso 1 1 calc R . .
O22 O 0.5820(2) 0.33567(13) 0.27099(7) 0.0221(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 0.0142(8) 0.0218(8) 0.0160(7) 0.0004(6) 0.0019(6) 0.0038(7)
C2 0.0145(8) 0.0209(8) 0.0148(7) -0.0002(6) -0.0004(6) 0.0002(7)
C3 0.0149(8) 0.0218(8) 0.0161(8) 0.0000(7) -0.0010(6) 0.0000(7)
C4 0.0124(8) 0.0240(8) 0.0174(7) 0.0005(6) -0.0022(7) -0.0008(7)
O1A 0.0243(7) 0.0241(6) 0.0221(6) 0.0049(5) 0.0003(6) -0.0026(6)
O1B 0.0240(7) 0.0279(6) 0.0164(6) 0.0037(5) -0.0052(5) -0.0018(6)
O2 0.0155(6) 0.0202(6) 0.0209(6) 0.0002(5) 0.0012(5) -0.0012(5)
O3 0.0148(6) 0.0334(7) 0.0175(6) -0.0014(5) 0.0024(5) 0.0043(6)
O4A 0.0269(7) 0.0243(6) 0.0169(6) -0.0011(5) -0.0057(5) 0.0043(6)
O4B 0.0234(7) 0.0224(6) 0.0204(6) -0.0001(5) -0.0036(5) 0.0040(6)
C22 0.0192(8) 0.0205(8) 0.0156(7) 0.0022(6) 0.0005(7) -0.0019(7)
C24 0.0184(9) 0.0276(9) 0.0230(8) 0.0018(7) -0.0025(7) 0.0028(8)
C25 0.0331(11) 0.0380(11) 0.0238(9) -0.0052(8) -0.0053(8) 0.0173(10)
N21 0.0257(8) 0.0304(8) 0.0192(7) -0.0058(6) -0.0052(6) 0.0090(8)
N23 0.0265(8) 0.0266(7) 0.0200(7) -0.0036(6) -0.0066(7) 0.0043(7)
O22 0.0225(6) 0.0275(6) 0.0164(5) -0.0011(5) -0.0004(5) 0.0054(6)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 O1A 1.210(2) . ?
C1 O1B 1.321(2) . ?
C1 C2 1.533(2) . ?
C2 O2 1.406(2) . ?
C2 C3 1.533(2) . ?
C2 H2 1.0000 . ?
C3 O3 1.411(2) . ?
C3 C4 1.525(2) . ?
C3 H3 1.0000 . ?
C4 O4B 1.211(2) . ?
C4 O4A 1.323(2) . ?
O1B H1 0.8400 . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
O4A H4 0.8400 . ?
C22 O22 1.262(2) . ?
C22 N21 1.337(2) . ?
C22 N23 1.341(2) . ?
C24 N23 1.461(2) . ?
C24 C25 1.535(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.458(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N21 H21 0.8800 . ?
N23 H23 0.8800 . ?

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
O1A C1 O1B 125.23(16) . . ?
O1A C1 C2 121.69(16) . . ?
O1B C1 C2 113.08(15) . . ?
O2 C2 C3 112.67(14) . . ?
O2 C2 C1 115.09(15) . . ?
C3 C2 C1 106.65(14) . . ?
O2 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
O3 C3 C4 110.84(15) . . ?
O3 C3 C2 106.94(14) . . ?
C4 C3 C2 109.26(14) . . ?
O3 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
O4B C4 O4A 124.21(16) . . ?
O4B C4 C3 123.93(16) . . ?
O4A C4 C3 111.86(15) . . ?
C1 O1B H1 109.5 . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
C4 O4A H4 109.5 . . ?
O22 C22 N21 125.24(16) . . ?
O22 C22 N23 125.22(16) . . ?
N21 C22 N23 109.54(16) . . ?
N23 C24 C25 101.64(15) . . ?
N23 C24 H24A 111.4 . . ?
C25 C24 H24A 111.4 . . ?
N23 C24 H24B 111.4 . . ?
C25 C24 H24B 111.4 . . ?
H24A C24 H24B 109.3 . . ?
N21 C25 C24 102.46(15) . . ?
N21 C25 H25A 111.3 . . ?
C24 C25 H25A 111.3 . . ?
N21 C25 H25B 111.3 . . ?
C24 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
C22 N21 C25 111.18(15) . . ?
C22 N21 H21 124.4 . . ?
C25 N21 H21 124.4 . . ?
C22 N23 C24 111.78(15) . . ?
C22 N23 H23 124.1 . . ?
C24 N23 H23 124.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1B H1 O22 0.84 1.78 2.6090(18) 167.9 2_664
O2 H2O O4B 0.84 2.02 2.8145(18) 157.3 4_455
O3 H3O O2 0.84 2.30 2.977(2) 137.5 1_655
O3 H3O O1B 0.84 2.54 3.215(2) 137.9 1_655
O4A H4 O22 0.84 1.82 2.6359(18) 164.1 1_655
N21 H21 O4B 0.88 2.17 2.911(2) 141.1 1_455
N23 H23 O1A 0.88 2.24 2.926(2) 134.7 2_765

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        26.59
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.041


