# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb1
_database_code_depnum_ccdc_archive 'CCDC 918259'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O6, H2 O'
_chemical_formula_sum            'C20 H24 N4 O7'
_chemical_formula_weight         432.43
_chemical_absolute_configuration syn

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

_cell_length_a                   27.963(13)
_cell_length_b                   5.091(2)
_cell_length_c                   16.890(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.873(7)
_cell_angle_gamma                90.00
_cell_volume                     2105.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3166
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.43

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.175
_exptl_crystal_density_meas      1.364
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_crystal_F_000'            912.49
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9268
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.88
_reflns_number_total             2275
_reflns_number_gt                1630
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of 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)+(0.1114P)²+0.9064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2275
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_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
O1S O 0.0000 0.0285(5) 0.2500 0.0663(6) Uani 1 2 d S . .
O1 O 0.15588(6) 0.6535(3) 0.46291(10) 0.0585(4) Uani 1 1 d . . .
O2 O 0.08078(6) 0.4123(3) 0.38341(11) 0.0674(5) Uani 1 1 d . . .
O3 O 0.15205(6) -0.3371(3) 0.17131(10) 0.0602(4) Uani 1 1 d . . .
N1 N 0.13306(6) 0.1352(3) 0.30857(9) 0.0413(4) Uani 1 1 d . . .
N2 N 0.07833(6) -0.2541(3) 0.19003(10) 0.0466(4) Uani 1 1 d . . .
H2 H 0.0649 -0.1555 0.2157 0.056 Uiso 1 1 calc R . .
C1 C 0.12746(11) 0.7947(4) 0.50228(18) 0.0715(7) Uani 1 1 d . . .
H1A H 0.0942 0.8670 0.4549 0.107 Uiso 1 1 calc R . .
H1B H 0.1502 0.9342 0.5398 0.107 Uiso 1 1 calc R . .
H1C H 0.1191 0.6765 0.5382 0.107 Uiso 1 1 calc R . .
C2 C 0.12722(8) 0.4650(3) 0.40420(12) 0.0455(4) Uani 1 1 d . . .
C3 C 0.16008(7) 0.3253(3) 0.36860(11) 0.0406(4) Uani 1 1 d . . .
C4 C 0.16030(7) 0.0015(3) 0.27487(11) 0.0406(4) Uani 1 1 d . . .
C5 C 0.12943(7) -0.2117(3) 0.20662(12) 0.0436(4) Uani 1 1 d . . .
C6 C 0.04459(8) -0.4626(4) 0.12964(12) 0.0490(4) Uani 1 1 d . . .
H6A H 0.0170 -0.5117 0.1460 0.059 Uiso 1 1 calc R . .
H6B H 0.0673 -0.6155 0.1383 0.059 Uiso 1 1 calc R . .
C30 C 0.01652(7) -0.3865(3) 0.03033(12) 0.0444(4) Uani 1 1 d . . .
H7A H 0.0438 -0.3320 0.0139 0.053 Uiso 1 1 calc R . .
H7B H -0.0075 -0.2385 0.0207 0.053 Uiso 1 1 calc R . .
C8 C 0.21502(7) 0.0462(4) 0.30026(12) 0.0483(4) Uani 1 1 d . . .
H8 H 0.2326 -0.0527 0.2757 0.058 Uiso 1 1 calc R . .
C9 C 0.24242(7) 0.2415(4) 0.36281(12) 0.0513(5) Uani 1 1 d . . .
H9 H 0.2790 0.2750 0.3817 0.062 Uiso 1 1 calc R . .
C10 C 0.21468(7) 0.3864(4) 0.39706(12) 0.0473(4) Uani 1 1 d . . .
H10 H 0.2320 0.5215 0.4381 0.057 Uiso 1 1 calc R . .
H40 H 0.0256(12) 0.130(6) 0.285(2) 0.106(11) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1S 0.0565(14) 0.0674(13) 0.0768(15) 0.000 0.0335(12) 0.000
O1 0.0581(9) 0.0588(8) 0.0673(9) -0.0165(6) 0.0372(7) -0.0119(6)
O2 0.0462(8) 0.0831(10) 0.0817(11) -0.0248(8) 0.0377(8) -0.0089(7)
O3 0.0504(8) 0.0710(9) 0.0701(9) -0.0196(7) 0.0376(7) -0.0071(6)
N1 0.0358(8) 0.0490(8) 0.0397(7) 0.0034(6) 0.0188(6) -0.0003(6)
N2 0.0393(8) 0.0550(9) 0.0488(8) -0.0076(6) 0.0239(7) -0.0052(6)
C1 0.0867(17) 0.0590(12) 0.0900(17) -0.0207(11) 0.0594(15) -0.0105(11)
C2 0.0436(10) 0.0490(9) 0.0471(9) 0.0020(7) 0.0246(8) -0.0005(7)
C3 0.0366(9) 0.0457(9) 0.0394(9) 0.0053(6) 0.0182(7) -0.0005(7)
C4 0.0351(9) 0.0482(9) 0.0405(9) 0.0034(7) 0.0198(7) 0.0004(7)
C5 0.0404(10) 0.0497(9) 0.0441(9) 0.0024(7) 0.0231(8) -0.0004(7)
C6 0.0458(10) 0.0500(9) 0.0516(11) -0.0012(7) 0.0237(9) -0.0092(8)
C30 0.0406(10) 0.0410(9) 0.0513(10) 0.0016(7) 0.0220(8) -0.0030(7)
C8 0.0395(10) 0.0605(10) 0.0503(10) -0.0010(8) 0.0259(8) 0.0003(8)
C9 0.0360(9) 0.0672(11) 0.0521(10) -0.0016(8) 0.0225(8) -0.0083(8)
C10 0.0406(10) 0.0558(10) 0.0432(9) -0.0025(7) 0.0183(8) -0.0086(7)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1S H40 0.85(3) . ?
O1 C2 1.334(2) . ?
O1 C1 1.450(2) . ?
O2 C2 1.201(2) . ?
O3 C5 1.236(2) . ?
N1 C4 1.337(2) . ?
N1 C3 1.340(2) . ?
N2 C5 1.334(2) . ?
N2 C6 1.459(2) . ?
N2 H2 0.8600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.498(2) . ?
C3 C10 1.396(2) . ?
C4 C8 1.394(2) . ?
C4 C5 1.514(2) . ?
C6 C30 1.519(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C30 C30 1.525(3) 5_545 ?
C30 H7A 0.9700 . ?
C30 H7B 0.9700 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 115.61(16) . . ?
C4 N1 C3 117.45(15) . . ?
C5 N2 C6 122.00(15) . . ?
C5 N2 H2 119.0 . . ?
C6 N2 H2 119.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.72(17) . . ?
O2 C2 C3 124.25(17) . . ?
O1 C2 C3 112.03(15) . . ?
N1 C3 C10 123.00(16) . . ?
N1 C3 C2 114.55(15) . . ?
C10 C3 C2 122.45(16) . . ?
N1 C4 C8 123.52(16) . . ?
N1 C4 C5 117.19(14) . . ?
C8 C4 C5 119.28(15) . . ?
O3 C5 N2 124.12(17) . . ?
O3 C5 C4 120.08(15) . . ?
N2 C5 C4 115.79(14) . . ?
N2 C6 C30 113.65(14) . . ?
N2 C6 H6A 108.8 . . ?
C30 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C30 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C30 C30 111.75(17) . 5_545 ?
C6 C30 H7A 109.3 . . ?
C30 C30 H7A 109.3 5_545 . ?
C6 C30 H7B 109.3 . . ?
C30 C30 H7B 109.3 5_545 . ?
H7A C30 H7B 107.9 . . ?
C9 C8 C4 118.27(16) . . ?
C9 C8 H8 120.9 . . ?
C4 C8 H8 120.9 . . ?
C8 C9 C10 119.18(17) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C3 118.55(17) . . ?
C9 C10 H10 120.7 . . ?
C3 C10 H10 120.7 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.090
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb6
_database_code_depnum_ccdc_archive 'CCDC 918261'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 N4 O6, 2(H2 O)'
_chemical_formula_sum            'C21 H28 N4 O8'
_chemical_formula_weight         464.47
_chemical_absolute_configuration syn

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   '
_symmetry_space_group_name_Hall  'C 2y'

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

_cell_length_a                   18.863(16)
_cell_length_b                   4.534(4)
_cell_length_c                   14.980(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.37(2)
_cell_angle_gamma                90.00
_cell_volume                     1176.1(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1461
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.07

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.174
_exptl_crystal_density_meas      1.312
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_crystal_F_000'            492.27
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3543
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         24.91
_reflns_number_total             2066
_reflns_number_gt                1340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of 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)+(0.0845P)²+0.2503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(18)
_refine_ls_number_reflns         1608
_refine_ls_number_parameters     140
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_restrained_S_all      0.845
_refine_ls_shift/su_max          0.006
_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
O1S O 0.77208(14) -0.0124(6) 0.05771(15) 0.0656(6) Uani 1 1 d . . .
O1 O 0.97716(10) 0.5761(5) 0.32651(13) 0.0603(6) Uani 1 1 d . . .
O2 O 0.67822(11) -0.3470(5) 0.32496(13) 0.0655(6) Uani 1 1 d . . .
O3 O 0.90444(11) 0.3317(6) 0.19070(13) 0.0753(8) Uani 1 1 d . . .
N1 N 0.82091(10) 0.0851(4) 0.28638(12) 0.0386(5) Uani 1 1 d . . .
N2 N 0.70248(10) -0.2905(5) 0.18954(12) 0.0434(5) Uani 1 1 d . . .
H2 H 0.7325 -0.2115 0.1655 0.052 Uiso 1 1 calc R . .
C1 C 1.02331(17) 0.6977(9) 0.2776(2) 0.0746(9) Uani 1 1 d . . .
H1A H 1.0504 0.5413 0.2614 0.112 Uiso 1 1 calc R . .
H1B H 1.0598 0.8360 0.3197 0.112 Uiso 1 1 calc R . .
H1C H 0.9902 0.7962 0.2192 0.112 Uiso 1 1 calc R . .
C2 C 0.91956(13) 0.3956(7) 0.27416(18) 0.0483(6) Uani 1 1 d . . .
C3 C 0.87724(12) 0.2782(6) 0.33266(14) 0.0412(6) Uani 1 1 d . . .
C4 C 0.78137(12) -0.0271(6) 0.33551(15) 0.0387(5) Uani 1 1 d . . .
C5 C 0.71595(12) -0.2374(6) 0.28244(16) 0.0425(6) Uani 1 1 d . . .
C6 C 0.63905(12) -0.4769(6) 0.12675(17) 0.0450(6) Uani 1 1 d . . .
H6A H 0.6242 -0.6110 0.1668 0.054 Uiso 1 1 calc R . .
H6B H 0.6567 -0.5944 0.0854 0.054 Uiso 1 1 calc R . .
C7 C 0.56903(12) -0.2989(6) 0.06343(18) 0.0501(6) Uani 1 1 d . . .
H7A H 0.5838 -0.1711 0.0217 0.060 Uiso 1 1 calc R . .
H7B H 0.5534 -0.1741 0.1050 0.060 Uiso 1 1 calc R . .
C8 C 0.5000 -0.4841(9) 0.0000 0.0462(8) Uani 1 2 d S . .
H8A H 0.4846 -0.6102 0.0415 0.055 Uiso 0.50 1 calc PR . .
H8B H 0.5154 -0.6102 -0.0415 0.055 Uiso 0.50 1 calc PR . .
C9 C 0.89608(13) 0.3655(7) 0.42835(16) 0.0493(6) Uani 1 1 d . . .
H9 H 0.9347 0.5043 0.4576 0.059 Uiso 1 1 calc R . .
C10 C 0.85628(13) 0.2416(8) 0.47886(16) 0.0535(7) Uani 1 1 d . . .
H10 H 0.8686 0.2910 0.5436 0.064 Uiso 1 1 calc R . .
C11 C 0.79830(13) 0.0445(6) 0.43206(16) 0.0473(6) Uani 1 1 d . . .
H11 H 0.7705 -0.0407 0.4646 0.057 Uiso 1 1 calc R . .
H40 H 0.815(2) 0.035(15) 0.106(3) 0.138(18) Uiso 1 1 d . . .
H41 H 0.749(3) 0.141(14) 0.013(4) 0.130(17) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1S 0.0838(14) 0.0610(13) 0.0474(11) -0.0001(11) 0.0211(11) -0.0102(12)
O1 0.0516(9) 0.0694(14) 0.0640(11) -0.0050(11) 0.0274(9) -0.0192(11)
O2 0.0678(11) 0.0799(15) 0.0599(10) -0.0059(10) 0.0372(9) -0.0252(11)
O3 0.0798(13) 0.104(2) 0.0506(10) -0.0136(12) 0.0350(10) -0.0349(14)
N1 0.0333(9) 0.0444(12) 0.0362(9) 0.0013(9) 0.0119(8) 0.0006(9)
N2 0.0389(10) 0.0469(13) 0.0423(10) 0.0020(10) 0.0137(8) -0.0056(10)
C1 0.0668(17) 0.077(2) 0.090(2) 0.0063(19) 0.0418(17) -0.0232(18)
C2 0.0417(12) 0.0548(16) 0.0485(13) 0.0002(12) 0.0180(10) -0.0043(13)
C3 0.0322(11) 0.0509(15) 0.0387(11) -0.0023(12) 0.0121(9) -0.0006(11)
C4 0.0353(10) 0.0436(13) 0.0375(10) 0.0033(11) 0.0147(9) 0.0047(11)
C5 0.0408(12) 0.0442(14) 0.0444(11) 0.0052(12) 0.0189(10) 0.0017(11)
C6 0.0409(12) 0.0428(15) 0.0478(12) -0.0027(12) 0.0137(10) -0.0040(12)
C7 0.0481(13) 0.0390(14) 0.0527(13) -0.0021(12) 0.0089(11) -0.0034(13)
C8 0.0463(17) 0.040(2) 0.0469(17) 0.000 0.0123(15) 0.000
C9 0.0367(11) 0.0626(17) 0.0447(12) -0.0108(13) 0.0121(10) -0.0055(12)
C10 0.0466(13) 0.078(2) 0.0365(11) -0.0103(15) 0.0171(10) -0.0028(15)
C11 0.0448(12) 0.0605(17) 0.0412(11) 0.0012(13) 0.0221(10) 0.0005(13)

_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
O1S H40 0.87(4) . ?
O1S H41 0.94(6) . ?
O1 C2 1.337(3) . ?
O1 C1 1.451(3) . ?
O2 C5 1.232(3) . ?
O3 C2 1.202(3) . ?
N1 C3 1.339(3) . ?
N1 C4 1.339(3) . ?
N2 C5 1.334(3) . ?
N2 C6 1.462(3) . ?
N2 H2 0.8600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.498(3) . ?
C3 C9 1.390(3) . ?
C4 C11 1.390(3) . ?
C4 C5 1.512(3) . ?
C6 C7 1.517(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.524(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C7 1.524(3) 2_655 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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
H40 O1S H41 115(5) . . ?
C2 O1 C1 116.5(2) . . ?
C3 N1 C4 117.70(19) . . ?
C5 N2 C6 122.97(19) . . ?
C5 N2 H2 118.5 . . ?
C6 N2 H2 118.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 O1 124.0(2) . . ?
O3 C2 C3 124.1(2) . . ?
O1 C2 C3 111.8(2) . . ?
N1 C3 C9 123.1(2) . . ?
N1 C3 C2 115.29(19) . . ?
C9 C3 C2 121.6(2) . . ?
N1 C4 C11 122.3(2) . . ?
N1 C4 C5 117.85(19) . . ?
C11 C4 C5 119.81(19) . . ?
O2 C5 N2 123.8(2) . . ?
O2 C5 C4 120.0(2) . . ?
N2 C5 C4 116.13(18) . . ?
N2 C6 C7 112.5(2) . . ?
N2 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C8 114.4(2) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C7 113.1(3) . 2_655 ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 2_655 . ?
C7 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 2_655 . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C3 118.5(2) . . ?
C10 C9 H9 120.7 . . ?
C3 C9 H9 120.7 . . ?
C11 C10 C9 118.9(2) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C4 119.5(2) . . ?
C10 C11 H11 120.3 . . ?
C4 C11 H11 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        24.91
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.031
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb1
_database_code_depnum_ccdc_archive 'CCDC 918262'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N4 O6, H2 O'
_chemical_formula_sum            'C19 H22 N4 O7'
_chemical_formula_weight         418.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2 '
_symmetry_space_group_name_Hall  'P 2 2ab'

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

_cell_length_a                   21.196(11)
_cell_length_b                   4.605(3)
_cell_length_c                   10.551(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1029.9(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3102
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      20.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.172
_exptl_crystal_density_meas      1.349
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_crystal_F_000'            440.24
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14229
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.04
_reflns_number_total             1846
_reflns_number_gt                1406
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0918P)²+0.1440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(1)
_refine_ls_number_reflns         1846(1122)
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_restrained_S_all      0.833
_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
O1 O 0.85755(9) 0.2779(5) 0.40321(18) 0.0809(7) Uani 1 1 d . . .
O2 O 0.92639(10) 0.6085(5) 0.46960(18) 0.0859(7) Uani 1 1 d . . .
O3 O 0.84655(7) 0.8029(4) 1.02480(16) 0.0587(5) Uani 1 1 d . . .
N1 N 0.86893(8) 0.6138(4) 0.70298(16) 0.0442(5) Uani 1 1 d . . .
N2 N 0.91669(8) 0.9616(4) 0.87857(17) 0.0460(5) Uani 1 1 d . . .
H2 H 0.9289 0.9490 0.8010 0.055 Uiso 1 1 calc R . .
C1 C 0.89153(18) 0.2576(9) 0.2844(3) 0.0996(12) Uani 1 1 d . . .
H1A H 0.8922 0.4443 0.2440 0.149 Uiso 1 1 calc R . .
H1B H 0.8709 0.1199 0.2300 0.149 Uiso 1 1 calc R . .
H1C H 0.9340 0.1950 0.3004 0.149 Uiso 1 1 calc R . .
C2 C 0.88185(12) 0.4564(6) 0.4895(2) 0.0593(7) Uani 1 1 d . . .
C3 C 0.84557(10) 0.4447(5) 0.6113(2) 0.0486(6) Uani 1 1 d . . .
C4 C 0.83929(10) 0.6149(5) 0.8150(2) 0.0414(5) Uani 1 1 d . . .
C5 C 0.86766(9) 0.8034(5) 0.9160(2) 0.0422(5) Uani 1 1 d . . .
C6 C 0.95055(10) 1.1551(5) 0.9635(2) 0.0491(6) Uani 1 1 d . . .
H6A H 0.9206 1.2482 1.0198 0.059 Uiso 1 1 calc R . .
H6B H 0.9709 1.3058 0.9138 0.059 Uiso 1 1 calc R . .
C7 C 1.0000 1.0000 1.0421(3) 0.0496(8) Uani 1 2 d S . .
C8 C 0.78526(10) 0.4539(5) 0.8389(2) 0.0516(6) Uani 1 1 d . . .
H8 H 0.7654 0.4627 0.9174 0.062 Uiso 1 1 calc R . .
C9 C 0.76183(12) 0.2814(6) 0.7441(3) 0.0612(7) Uani 1 1 d . . .
H9 H 0.7258 0.1700 0.7574 0.073 Uiso 1 1 calc R . .
C10 C 0.79244(11) 0.2752(6) 0.6279(3) 0.0577(7) Uani 1 1 d . . .
H10 H 0.7775 0.1590 0.5624 0.069 Uiso 1 1 calc R . .
O1SA O 1.0000 1.0000 0.6443(3) 0.0824(9) Uani 1 2 d S . .
H40A H 1.0243(16) 1.120(8) 0.592(3) 0.106(12) Uiso 1 1 d . . .
H7A H 1.0206(11) 1.149(6) 1.097(2) 0.059(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0906(14) 0.0982(15) 0.0540(11) -0.0290(11) 0.0077(10) -0.0116(12)
O2 0.0809(12) 0.1203(17) 0.0564(12) -0.0175(12) 0.0173(10) -0.0254(14)
O3 0.0548(9) 0.0733(11) 0.0480(10) -0.0096(9) 0.0129(8) -0.0065(8)
N1 0.0409(9) 0.0509(10) 0.0408(10) -0.0013(9) 0.0007(8) 0.0014(9)
N2 0.0443(10) 0.0537(11) 0.0399(10) -0.0034(9) 0.0032(8) -0.0028(9)
C1 0.119(3) 0.122(3) 0.0576(19) -0.032(2) 0.0207(18) -0.004(2)
C2 0.0583(15) 0.0719(16) 0.0479(15) -0.0077(13) -0.0006(12) 0.0019(13)
C3 0.0460(11) 0.0541(13) 0.0458(13) -0.0028(11) -0.0036(10) 0.0075(11)
C4 0.0363(10) 0.0449(11) 0.0430(12) -0.0006(9) 0.0020(9) 0.0060(9)
C5 0.0366(10) 0.0483(12) 0.0418(13) 0.0011(10) 0.0059(9) 0.0053(10)
C6 0.0478(12) 0.0464(12) 0.0532(14) -0.0071(12) 0.0026(10) -0.0022(10)
C7 0.0511(18) 0.0503(18) 0.0475(19) 0.000 0.000 -0.0066(15)
C8 0.0439(12) 0.0588(14) 0.0520(14) 0.0025(12) 0.0045(10) -0.0021(11)
C9 0.0447(12) 0.0681(17) 0.0709(17) -0.0032(14) -0.0012(12) -0.0102(12)
C10 0.0550(13) 0.0585(15) 0.0597(16) -0.0098(12) -0.0099(12) -0.0042(12)
O1SA 0.087(2) 0.105(2) 0.0555(18) 0.000 0.000 -0.0323(19)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.330(3) . ?
O1 C1 1.449(3) . ?
O2 C2 1.194(3) . ?
O3 C5 1.232(3) . ?
N1 C3 1.337(3) . ?
N1 C4 1.338(3) . ?
N2 C5 1.329(3) . ?
N2 C6 1.453(3) . ?
N2 H2 0.8600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.499(4) . ?
C3 C10 1.381(3) . ?
C4 C8 1.387(3) . ?
C4 C5 1.500(3) . ?
C6 C7 1.516(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C6 1.516(3) 4_775 ?
C7 H7A 1.00(2) . ?
C8 C9 1.371(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
O1SA H40A 0.93(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 116.1(2) . . ?
C3 N1 C4 117.86(19) . . ?
C5 N2 C6 122.64(19) . . ?
C5 N2 H2 118.7 . . ?
C6 N2 H2 118.7 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.3(2) . . ?
O2 C2 C3 125.2(2) . . ?
O1 C2 C3 111.5(2) . . ?
N1 C3 C10 122.6(2) . . ?
N1 C3 C2 114.2(2) . . ?
C10 C3 C2 123.2(2) . . ?
N1 C4 C8 123.1(2) . . ?
N1 C4 C5 116.18(18) . . ?
C8 C4 C5 120.7(2) . . ?
O3 C5 N2 124.2(2) . . ?
O3 C5 C4 121.02(19) . . ?
N2 C5 C4 114.81(19) . . ?
N2 C6 C7 112.96(17) . . ?
N2 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C6 113.6(3) . 4_775 ?
C6 C7 H7A 107.1(14) . . ?
C6 C7 H7A 109.8(13) 4_775 . ?
C9 C8 C4 118.4(2) . . ?
C9 C8 H8 120.8 . . ?
C4 C8 H8 120.8 . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C3 C10 C9 118.8(2) . . ?
C3 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.035
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1000665'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4 O6, 4(H2 O)'
_chemical_formula_sum            'C18 H26 N4 O10'
_chemical_formula_weight         458.43

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  '
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   6.886(7)
_cell_length_b                   19.68(2)
_cell_length_c                   16.336(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.08(2)
_cell_angle_gamma                90.00
_cell_volume                     2180(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1999
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.97

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.072
_exptl_crystal_density_meas      1.397
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_crystal_F_000'            968.59
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8156
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.57
_reflns_number_total             2051
_reflns_number_gt                1376
_reflns_threshold_expression     >2sigma(I)

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

_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. 
 Three bond distances and angles H1S H1S_$1, H1S H3S,  O1S H1S were 
 restrined using DFIX command.
;

_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)+(0.1000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2051
_refine_ls_number_parameters     196
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.2005
_refine_ls_wR_factor_gt          0.1755
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_restrained_S_all      1.295
_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
N2 N 0.0767(4) 0.09055(11) -0.00316(14) 0.0283(7) Uani 1 1 d . . .
O2 O -0.1461(4) 0.28203(9) -0.14909(12) 0.0344(6) Uani 1 1 d . . .
O1 O -0.1359(4) 0.38364(9) -0.08664(12) 0.0328(6) Uani 1 1 d . . .
N1 N 0.0114(4) 0.22311(11) -0.00102(13) 0.0251(6) Uani 1 1 d . . .
C8 C -0.1087(5) 0.31647(13) -0.08706(17) 0.0267(7) Uani 1 1 d . . .
C9 C -0.0241(4) 0.29007(13) -0.00231(16) 0.0243(7) Uani 1 1 d . . .
C10 C 0.0140(5) 0.33060(14) 0.06766(17) 0.0291(8) Uani 1 1 d . . .
C11 C 0.0915(5) 0.19542(13) 0.07215(16) 0.0252(7) Uani 1 1 d . . .
C12 C 0.1386(5) 0.23218(14) 0.14560(17) 0.0292(8) Uani 1 1 d . . .
C13 C 0.0981(5) 0.30120(14) 0.14276(17) 0.0312(8) Uani 1 1 d . . .
C14 C 0.1264(5) 0.11971(14) 0.07125(16) 0.0269(7) Uani 1 1 d . . .
C15 C -0.2042(6) 0.41352(16) -0.16817(19) 0.0374(10) Uani 1 1 d . . .
C16 C 0.0868(5) 0.01763(13) -0.01428(18) 0.0303(8) Uani 1 1 d . . .
O3 O 0.1938(4) 0.08907(9) 0.13612(12) 0.0327(6) Uani 1 1 d . . .
H12 H 0.211(5) 0.2093(15) 0.198(2) 0.038(9) Uiso 1 1 d . . .
H10 H -0.014(5) 0.3749(18) 0.0665(19) 0.038(9) Uiso 1 1 d . . .
H13 H 0.133(5) 0.3290(15) 0.1935(18) 0.032(8) Uiso 1 1 d . . .
H15C H -0.201(6) 0.461(2) -0.160(2) 0.046(10) Uiso 1 1 d . . .
H15B H -0.119(5) 0.3966(15) -0.208(2) 0.036(9) Uiso 1 1 d . . .
H15A H -0.344(7) 0.4013(19) -0.188(3) 0.067(14) Uiso 1 1 d . . .
H16A H 0.074(5) 0.0111(14) -0.072(2) 0.031(8) Uiso 1 1 d . . .
H16B H 0.223(5) -0.0023(15) 0.014(2) 0.035(9) Uiso 1 1 d . . .
H22 H 0.030(5) 0.1148(18) -0.047(2) 0.046(10) Uiso 1 1 d . . .
O2S O -0.0740(4) 0.14022(11) -0.17590(13) 0.0377(7) Uani 1 1 d . . .
H3S H -0.175(9) 0.114(2) -0.183(4) 0.14(3) Uiso 1 1 d D . .
H4S H -0.098(6) 0.179(2) -0.163(2) 0.051(12) Uiso 1 1 d . . .
O1S O -0.3573(4) 0.04134(11) -0.17921(14) 0.0427(7) Uani 1 1 d D . .
H2S H -0.298(6) 0.003(2) -0.164(3) 0.059(12) Uiso 1 1 d . . .
H1S H -0.3399(16) 0.024(2) -0.2300(15) 0.089 Uiso 1 1 d 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
N2 0.0464(19) 0.0180(12) 0.0189(12) -0.0015(9) 0.0008(11) 0.0005(11)
O2 0.0521(16) 0.0243(10) 0.0241(11) -0.0028(8) -0.0004(10) 0.0008(9)
O1 0.0560(16) 0.0183(10) 0.0238(11) 0.0025(8) 0.0063(10) 0.0034(9)
N1 0.0324(16) 0.0193(12) 0.0232(13) -0.0018(8) 0.0043(11) -0.0016(10)
C8 0.0321(19) 0.0207(13) 0.0269(15) -0.0015(11) 0.0039(13) -0.0018(12)
C9 0.0289(19) 0.0197(14) 0.0241(15) -0.0016(10) 0.0038(12) -0.0024(12)
C10 0.041(2) 0.0169(14) 0.0294(16) -0.0043(11) 0.0063(14) -0.0027(13)
C11 0.0316(19) 0.0209(14) 0.0226(14) -0.0004(11) 0.0032(13) -0.0027(12)
C12 0.040(2) 0.0251(15) 0.0215(15) -0.0026(11) 0.0034(14) -0.0027(13)
C13 0.046(2) 0.0242(15) 0.0230(15) -0.0058(12) 0.0037(13) -0.0049(13)
C14 0.035(2) 0.0222(14) 0.0236(15) -0.0019(11) 0.0046(13) -0.0011(13)
C15 0.063(3) 0.0242(16) 0.0247(16) 0.0061(12) 0.0083(17) 0.0027(16)
C16 0.049(2) 0.0159(13) 0.0241(15) -0.0040(11) 0.0019(15) 0.0027(13)
O3 0.0506(17) 0.0219(10) 0.0229(11) 0.0014(8) -0.0015(10) 0.0018(9)
O2S 0.0619(19) 0.0205(11) 0.0280(12) -0.0024(9) 0.0008(11) -0.0033(11)
O1S 0.0650(19) 0.0219(11) 0.0364(13) -0.0021(9) -0.0044(11) 0.0048(11)

_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
N2 C14 1.334(4) . ?
N2 C16 1.450(4) . ?
N2 H22 0.87(4) . ?
O2 C8 1.209(3) . ?
O1 C8 1.335(4) . ?
O1 C15 1.457(4) . ?
N1 C9 1.340(4) . ?
N1 C11 1.342(4) . ?
C8 C9 1.498(4) . ?
C9 C10 1.381(4) . ?
C10 C13 1.388(4) . ?
C10 H10 0.89(4) . ?
C11 C12 1.390(4) . ?
C11 C14 1.510(4) . ?
C12 C13 1.386(4) . ?
C12 H12 1.02(3) . ?
C13 H13 0.99(3) . ?
C14 O3 1.237(3) . ?
C15 H15C 0.95(4) . ?
C15 H15B 1.01(3) . ?
C15 H15A 0.99(5) . ?
C16 C16 1.524(7) 5 ?
C16 H16A 0.95(3) . ?
C16 H16B 1.05(3) . ?
O2S H3S 0.85(4) . ?
O2S H4S 0.82(4) . ?
O1S H2S 0.87(4) . ?
O1S H1S 0.93(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N2 C16 122.0(2) . . ?
C14 N2 H22 121(2) . . ?
C16 N2 H22 117(2) . . ?
C8 O1 C15 114.7(2) . . ?
C9 N1 C11 117.3(2) . . ?
O2 C8 O1 123.4(2) . . ?
O2 C8 C9 124.9(3) . . ?
O1 C8 C9 111.8(2) . . ?
N1 C9 C10 123.2(2) . . ?
N1 C9 C8 113.3(2) . . ?
C10 C9 C8 123.5(3) . . ?
C9 C10 C13 118.7(3) . . ?
C9 C10 H10 123(2) . . ?
C13 C10 H10 119(2) . . ?
N1 C11 C12 123.7(3) . . ?
N1 C11 C14 115.7(2) . . ?
C12 C11 C14 120.6(2) . . ?
C13 C12 C11 117.8(3) . . ?
C13 C12 H12 121.9(17) . . ?
C11 C12 H12 120.1(17) . . ?
C12 C13 C10 119.2(3) . . ?
C12 C13 H13 119.8(17) . . ?
C10 C13 H13 120.9(17) . . ?
O3 C14 N2 124.7(3) . . ?
O3 C14 C11 120.6(2) . . ?
N2 C14 C11 114.7(2) . . ?
O1 C15 H15C 106(2) . . ?
O1 C15 H15B 109.0(19) . . ?
H15C C15 H15B 115(3) . . ?
O1 C15 H15A 110(2) . . ?
H15C C15 H15A 106(3) . . ?
H15B C15 H15A 110(3) . . ?
N2 C16 C16 110.8(3) . 5 ?
N2 C16 H16A 105.2(17) . . ?
C16 C16 H16A 108(2) 5 . ?
N2 C16 H16B 112.0(16) . . ?
C16 C16 H16B 112.7(18) 5 . ?
H16A C16 H16B 108(3) . . ?
H3S O2S H4S 114(5) . . ?
H2S O1S H1S 79(3) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.57
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.094
