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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1b
#==============================================================================

# CHEMICAL DATA 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H13 N5, C4 O4, 2(H2 O)'
_chemical_formula_sum            'C8 H17 N5 O6'
_chemical_formula_weight         279.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca21
_symmetry_space_group_name_Hall  P2c-2ac

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

_cell_length_a                   12.809(2)
_cell_length_b                   13.372(2)
_cell_length_c                   7.3552(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1259.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1776
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      21.29

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#==============================================================================

# EXPERIMENTAL DATA  
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        'no decay'
_diffrn_reflns_number            14347
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_sigmaI/netI    0.0749
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         26.49
_reflns_number_total             2607
_reflns_number_gt                1985
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

#==============================================================================

# REFINEMENT DATA 

_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)+(0.0350P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(15)
_refine_ls_number_reflns         2607
_refine_ls_number_parameters     218
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.909
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 
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 1.04045(13) 0.26844(14) 0.3586(3) 0.0218(5) Uani 1 1 d . . .
O2 O 0.81594(14) 0.16428(14) 0.4198(3) 0.0224(5) Uani 1 1 d . . .
O3 O 0.70327(13) 0.36561(13) 0.2556(3) 0.0229(5) Uani 1 1 d . . .
O4 O 0.92958(13) 0.46222(14) 0.1869(3) 0.0183(5) Uani 1 1 d . . .
C1 C 0.9478(2) 0.2933(2) 0.3309(4) 0.0173(6) Uani 1 1 d . . .
C2 C 0.84537(19) 0.2467(2) 0.3594(4) 0.0153(6) Uani 1 1 d . . .
C3 C 0.7945(2) 0.33688(19) 0.2850(4) 0.0173(6) Uani 1 1 d . . .
C4 C 0.89685(19) 0.3810(2) 0.2546(4) 0.0159(6) Uani 1 1 d . . .
N1 N 0.53116(16) 0.81705(17) -0.0833(3) 0.0169(5) Uani 1 1 d . . .
N2 N 0.66565(17) 0.70542(17) -0.0323(3) 0.0163(5) Uani 1 1 d D . .
H20 H 0.7114(16) 0.7573(14) -0.018(4) 0.010(7) Uiso 1 1 d D . .
N3 N 0.64300(17) 0.54330(17) 0.0862(3) 0.0161(5) Uani 1 1 d D . .
H30 H 0.6743(19) 0.4870(16) 0.134(4) 0.024(8) Uiso 1 1 d D . .
H31 H 0.5746(14) 0.552(2) 0.104(4) 0.028(9) Uiso 1 1 d D . .
N4 N 0.51024(17) 0.65409(18) -0.1686(3) 0.0172(5) Uani 1 1 d D . .
H40 H 0.5374(19) 0.5956(14) -0.192(4) 0.018(8) Uiso 1 1 d D . .
H41 H 0.4410(14) 0.660(2) -0.178(4) 0.020(8) Uiso 1 1 d D . .
N5 N 0.80543(17) 0.60274(19) 0.0164(4) 0.0182(5) Uani 1 1 d D . .
H50 H 0.837(2) 0.5482(17) 0.064(4) 0.037(10) Uiso 1 1 d D . .
H51 H 0.843(2) 0.6489(19) -0.044(4) 0.039(10) Uiso 1 1 d D . .
C6 C 0.5796(2) 0.8950(2) 0.0279(4) 0.0254(7) Uani 1 1 d . . .
H6A H 0.6267 0.9351 -0.0477 0.038 Uiso 1 1 calc R . .
H6B H 0.6194 0.8640 0.1268 0.038 Uiso 1 1 calc R . .
H6C H 0.5252 0.9382 0.0791 0.038 Uiso 1 1 calc R . .
C5 C 0.4417(2) 0.8463(2) -0.1949(4) 0.0259(7) Uani 1 1 d . . .
H5A H 0.3772 0.8221 -0.1382 0.039 Uiso 1 1 calc R . .
H5B H 0.4487 0.8169 -0.3164 0.039 Uiso 1 1 calc R . .
H5C H 0.4392 0.9193 -0.2050 0.039 Uiso 1 1 calc R . .
C7 C 0.5671(2) 0.7252(2) -0.0935(4) 0.0157(6) Uani 1 1 d . . .
C8 C 0.70398(19) 0.6141(2) 0.0239(4) 0.0157(6) Uani 1 1 d . . .
O5 O 0.82000(16) 0.83818(17) 0.0445(4) 0.0352(6) Uani 1 1 d D . .
H150 H 0.817(3) 0.8986(16) 0.068(6) 0.086(17) Uiso 1 1 d D . .
H151 H 0.881(2) 0.825(3) 0.003(7) 0.108(19) Uiso 1 1 d D . .
O6 O 0.8039(2) 0.03392(17) 0.1283(4) 0.0382(6) Uani 1 1 d D . .
H160 H 0.766(3) 0.070(2) 0.057(5) 0.065(13) Uiso 1 1 d D . .
H161 H 0.812(3) 0.069(2) 0.224(4) 0.052(12) Uiso 1 1 d D . .


#==============================================================================

# MOLECULAR GEOMETRY 

_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 C1 1.249(3) . ?
O2 C2 1.247(3) . ?
O3 C3 1.248(3) . ?
O4 C4 1.266(3) . ?
C1 C4 1.455(4) . ?
C1 C2 1.467(4) . ?
C2 C3 1.476(4) . ?
C3 C4 1.456(4) . ?
N1 C7 1.313(3) . ?
N1 C5 1.463(3) . ?
N1 C6 1.463(3) . ?
N2 C7 1.366(3) . ?
N2 C8 1.379(3) . ?
N2 H20 0.914(16) . ?
N3 C8 1.310(3) . ?
N3 H30 0.923(17) . ?
N3 H31 0.894(17) . ?
N4 C7 1.319(3) . ?
N4 H40 0.873(17) . ?
N4 H41 0.893(17) . ?
N5 C8 1.309(3) . ?
N5 H50 0.905(17) . ?
N5 H51 0.903(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O5 H150 0.828(19) . ?
O5 H151 0.854(19) . ?
O6 H160 0.864(19) . ?
O6 H161 0.850(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 134.7(2) . . ?
O1 C1 C2 135.5(2) . . ?
C4 C1 C2 89.8(2) . . ?
O2 C2 C1 134.2(2) . . ?
O2 C2 C3 136.1(2) . . ?
C1 C2 C3 89.7(2) . . ?
O3 C3 C4 133.8(2) . . ?
O3 C3 C2 136.8(2) . . ?
C4 C3 C2 89.4(2) . . ?
O4 C4 C1 134.0(2) . . ?
O4 C4 C3 135.0(2) . . ?
C1 C4 C3 91.0(2) . . ?
C7 N1 C5 119.5(2) . . ?
C7 N1 C6 123.3(2) . . ?
C5 N1 C6 117.1(2) . . ?
C7 N2 C8 126.8(2) . . ?
C7 N2 H20 118.8(15) . . ?
C8 N2 H20 114.2(15) . . ?
C8 N3 H30 117.6(16) . . ?
C8 N3 H31 122.5(19) . . ?
H30 N3 H31 119(3) . . ?
C7 N4 H40 120.5(18) . . ?
C7 N4 H41 121.5(18) . . ?
H40 N4 H41 117(2) . . ?
C8 N5 H50 122(2) . . ?
C8 N5 H51 118(2) . . ?
H50 N5 H51 120(3) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C7 N4 120.3(2) . . ?
N1 C7 N2 119.1(2) . . ?
N4 C7 N2 120.5(2) . . ?
N5 C8 N3 121.5(3) . . ?
N5 C8 N2 116.3(3) . . ?
N3 C8 N2 122.2(2) . . ?
H150 O5 H151 108(4) . . ?
H160 O6 H161 106(3) . . ?

_diffrn_measured_fraction_theta_max .999
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full .999
_refine_diff_density_max         .230
_refine_diff_density_min         -.170
_refine_diff_density_rms         .045
_database_code_depnum_ccdc_archive 'CCDC 1018218'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1c
#==============================================================================
# CHEMICAL DATA 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H13 N5, C4 O4, H2O'
_chemical_formula_sum            'C8 H15 N5 O5'
_chemical_formula_weight         261.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA 

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_space_group_name_Hall  P2yb

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

_cell_length_a                   7.1418(9)
_cell_length_b                   10.6881(13)
_cell_length_c                   15.8359(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.827(2)
_cell_angle_gamma                90.00
_cell_volume                     1207.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4754
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.25

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#==============================================================================

# EXPERIMENTAL DATA 

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14473
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         26.38
_reflns_number_total             4898
_reflns_number_gt                4253
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (2001)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

#==============================================================================

# REFINEMENT DATA

_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)+(0.0301P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(9)
_refine_ls_number_reflns         4898
_refine_ls_number_parameters     401
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 
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 0.35462(18) 0.85400(14) 0.62627(8) 0.0207(3) Uani 1 1 d . . .
O2 O 0.27731(17) 0.77518(14) 0.82033(8) 0.0191(3) Uani 1 1 d . . .
O3 O 0.67300(18) 0.88961(14) 0.88187(8) 0.0206(3) Uani 1 1 d . . .
O4 O 0.75296(17) 0.96804(14) 0.68805(8) 0.0199(3) Uani 1 1 d . . .
C1 C 0.4412(3) 0.8640(2) 0.69660(11) 0.0156(4) Uani 1 1 d . . .
C2 C 0.4063(3) 0.82784(19) 0.78368(12) 0.0158(4) Uani 1 1 d . . .
C3 C 0.5858(3) 0.8810(2) 0.81136(12) 0.0174(5) Uani 1 1 d . . .
C4 C 0.6200(3) 0.91688(19) 0.72473(11) 0.0170(5) Uani 1 1 d . . .
O5 O 0.6922(2) 0.70396(14) 0.30389(8) 0.0277(4) Uani 1 1 d . . .
O6 O 0.43913(19) 0.76628(15) 0.13670(9) 0.0274(4) Uani 1 1 d . . .
O7 O 0.3459(2) 1.04129(15) 0.21370(8) 0.0267(4) Uani 1 1 d . . .
O8 O 0.5975(2) 0.97847(15) 0.38043(8) 0.0298(4) Uani 1 1 d . . .
C5 C 0.5961(3) 0.7978(2) 0.27912(12) 0.0218(5) Uani 1 1 d . . .
C6 C 0.4823(3) 0.8250(2) 0.20321(13) 0.0204(5) Uani 1 1 d . . .
C7 C 0.4409(3) 0.9491(2) 0.23769(12) 0.0189(5) Uani 1 1 d . . .
C8 C 0.5554(3) 0.9200(2) 0.31397(12) 0.0208(5) Uani 1 1 d . . .
N1 N -0.0743(2) 0.30605(17) 0.54030(10) 0.0196(4) Uani 1 1 d . . .
N2 N -0.0168(2) 0.26236(17) 0.40175(10) 0.0182(4) Uani 1 1 d D . .
H20 H -0.140(2) 0.287(2) 0.3836(13) 0.045(7) Uiso 1 1 d D . .
N3 N 0.2684(2) 0.16778(18) 0.37560(11) 0.0199(4) Uani 1 1 d D . .
H30 H 0.299(3) 0.156(2) 0.4317(10) 0.020(6) Uiso 1 1 d D . .
H31 H 0.348(3) 0.129(3) 0.3413(13) 0.046(8) Uiso 1 1 d D . .
N4 N 0.1943(2) 0.38305(18) 0.48295(11) 0.0199(4) Uani 1 1 d D . .
H40 H 0.239(3) 0.404(3) 0.4314(11) 0.048(8) Uiso 1 1 d D . .
H41 H 0.258(3) 0.410(2) 0.5326(10) 0.024(6) Uiso 1 1 d D . .
N5 N 0.0439(2) 0.19362(19) 0.26851(10) 0.0213(4) Uani 1 1 d D . .
H50 H 0.116(2) 0.1473(17) 0.2361(10) 0.011(5) Uiso 1 1 d D . .
H51 H -0.065(2) 0.232(2) 0.2459(13) 0.038(7) Uiso 1 1 d D . .
C9 C -0.0472(3) 0.3821(2) 0.61639(12) 0.0272(5) Uani 1 1 d . . .
H9A H 0.0224 0.3339 0.6602 0.041 Uiso 1 1 calc R . .
H9B H -0.1695 0.4060 0.6368 0.041 Uiso 1 1 calc R . .
H9C H 0.0237 0.4576 0.6033 0.041 Uiso 1 1 calc R . .
C10 C -0.2286(3) 0.2157(2) 0.54135(13) 0.0274(5) Uani 1 1 d . . .
H10A H -0.3485 0.2603 0.5376 0.041 Uiso 1 1 calc R . .
H10B H -0.2187 0.1675 0.5940 0.041 Uiso 1 1 calc R . .
H10C H -0.2216 0.1587 0.4931 0.041 Uiso 1 1 calc R . .
C11 C 0.0393(3) 0.31782(18) 0.47765(12) 0.0164(4) Uani 1 1 d . . .
C12 C 0.1031(3) 0.2085(2) 0.34820(12) 0.0174(5) Uani 1 1 d . . .
C13 C -0.0123(3) -0.1528(2) 1.12855(12) 0.0262(5) Uani 1 1 d . . .
H13A H 0.0496 -0.2314 1.1144 0.039 Uiso 1 1 calc R . .
H13B H -0.1333 -0.1712 1.1524 0.039 Uiso 1 1 calc R . .
H13C H 0.0669 -0.1066 1.1701 0.039 Uiso 1 1 calc R . .
C14 C -0.1955(3) 0.0138(2) 1.05467(13) 0.0267(5) Uani 1 1 d . . .
H14A H -0.1796 0.0773 1.0110 0.040 Uiso 1 1 calc R . .
H14B H -0.1932 0.0541 1.1103 0.040 Uiso 1 1 calc R . .
H14C H -0.3158 -0.0289 1.0441 0.040 Uiso 1 1 calc R . .
C15 C 0.0716(3) -0.08612(19) 0.98916(12) 0.0172(4) Uani 1 1 d . . .
C16 C 0.1320(3) 0.02905(19) 0.86128(12) 0.0160(5) Uani 1 1 d . . .
N6 N -0.0422(2) -0.07779(16) 1.05259(9) 0.0180(4) Uani 1 1 d . . .
N7 N 0.0143(2) -0.03059(17) 0.91406(10) 0.0180(4) Uani 1 1 d D . .
H70 H -0.106(2) -0.043(2) 0.8947(12) 0.033(7) Uiso 1 1 d D . .
N8 N 0.0763(2) 0.04461(18) 0.78211(11) 0.0203(4) Uani 1 1 d D . .
H80 H -0.027(2) 0.018(2) 0.7614(11) 0.017(6) Uiso 1 1 d D . .
H81 H 0.160(3) 0.088(2) 0.7484(14) 0.065(9) Uiso 1 1 d D . .
N9 N 0.2282(2) -0.15111(18) 0.99438(10) 0.0184(4) Uani 1 1 d D . .
H90 H 0.298(3) -0.172(2) 1.0440(11) 0.035(7) Uiso 1 1 d D . .
H91 H 0.287(3) -0.166(2) 0.9452(10) 0.024(6) Uiso 1 1 d D . .
N10 N 0.2927(2) 0.07204(18) 0.89187(11) 0.0192(4) Uani 1 1 d D . .
H100 H 0.316(3) 0.081(2) 0.9466(10) 0.032(7) Uiso 1 1 d D . .
H101 H 0.366(3) 0.110(2) 0.8576(11) 0.030(7) Uiso 1 1 d D . .
O9 O 0.7058(4) 0.6426(2) 0.94191(12) 0.0555(7) Uani 1 1 d D . .
H109 H 0.624(5) 0.601(4) 0.908(2) 0.18(2) Uiso 1 1 d D . .
H209 H 0.689(3) 0.7213(17) 0.9282(15) 0.046(8) Uiso 1 1 d D . .
O10 O 0.2879(3) 1.08970(19) 0.54221(11) 0.0428(5) Uani 1 1 d D . .
H110 H 0.336(4) 1.0214(19) 0.5527(16) 0.055(9) Uiso 1 1 d D . .
H210 H 0.292(3) 1.1314(19) 0.5917(10) 0.022(6) Uiso 1 1 d D . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.251(2) . ?
O2 C2 1.247(2) . ?
O3 C3 1.255(2) . ?
O4 C4 1.262(2) . ?
C1 C4 1.447(3) . ?
C1 C2 1.465(3) . ?
C2 C3 1.450(3) . ?
C3 C4 1.456(3) . ?
O5 C5 1.267(2) . ?
O6 C6 1.251(2) . ?
O7 C7 1.245(3) . ?
O8 C8 1.248(2) . ?
C5 C6 1.447(3) . ?
C5 C8 1.453(3) . ?
C6 C7 1.471(3) . ?
C7 C8 1.459(3) . ?
N1 C11 1.318(2) . ?
N1 C9 1.459(3) . ?
N1 C10 1.466(3) . ?
N2 C12 1.362(3) . ?
N2 C11 1.382(2) . ?
N2 H20 0.950(15) . ?
N3 C12 1.312(2) . ?
N3 H30 0.914(14) . ?
N3 H31 0.908(16) . ?
N4 C11 1.307(3) . ?
N4 H40 0.919(16) . ?
N4 H41 0.935(15) . ?
N5 C12 1.320(2) . ?
N5 H50 0.894(14) . ?
N5 H51 0.938(15) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 N6 1.453(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N6 1.470(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N9 1.316(3) . ?
C15 N6 1.326(2) . ?
C15 N7 1.373(2) . ?
C16 N10 1.307(2) . ?
C16 N8 1.307(2) . ?
C16 N7 1.372(3) . ?
N7 H70 0.907(15) . ?
N8 H80 0.839(14) . ?
N8 H81 0.938(17) . ?
N9 H90 0.935(15) . ?
N9 H91 0.917(14) . ?
N10 H100 0.880(15) . ?
N10 H101 0.875(15) . ?
O9 H109 0.887(19) . ?
O9 H209 0.877(17) . ?
O10 H110 0.820(17) . ?
O10 H210 0.900(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 134.21(19) . . ?
O1 C1 C2 135.71(19) . . ?
C4 C1 C2 90.09(14) . . ?
O2 C2 C3 134.31(18) . . ?
O2 C2 C1 136.11(17) . . ?
C3 C2 C1 89.57(17) . . ?
O3 C3 C2 133.63(19) . . ?
O3 C3 C4 136.06(19) . . ?
C2 C3 C4 90.30(14) . . ?
O4 C4 C1 134.46(17) . . ?
O4 C4 C3 135.44(17) . . ?
C1 C4 C3 90.04(17) . . ?
O5 C5 C6 133.6(2) . . ?
O5 C5 C8 135.21(18) . . ?
C6 C5 C8 91.19(17) . . ?
O6 C6 C5 134.7(2) . . ?
O6 C6 C7 135.97(19) . . ?
C5 C6 C7 89.29(16) . . ?
O7 C7 C8 134.16(19) . . ?
O7 C7 C6 135.84(19) . . ?
C8 C7 C6 89.99(17) . . ?
O8 C8 C5 136.58(19) . . ?
O8 C8 C7 133.9(2) . . ?
C5 C8 C7 89.53(15) . . ?
C11 N1 C9 120.47(18) . . ?
C11 N1 C10 124.21(17) . . ?
C9 N1 C10 115.28(16) . . ?
C12 N2 C11 123.96(16) . . ?
C12 N2 H20 121.9(14) . . ?
C11 N2 H20 111.8(14) . . ?
C12 N3 H30 122.6(13) . . ?
C12 N3 H31 122.4(15) . . ?
H30 N3 H31 113(2) . . ?
C11 N4 H40 113.7(15) . . ?
C11 N4 H41 126.4(13) . . ?
H40 N4 H41 120(2) . . ?
C12 N5 H50 116.7(11) . . ?
C12 N5 H51 122.3(14) . . ?
H50 N5 H51 120.9(17) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 N1 123.59(18) . . ?
N4 C11 N2 119.54(18) . . ?
N1 C11 N2 116.79(17) . . ?
N3 C12 N5 121.10(19) . . ?
N3 C12 N2 121.15(18) . . ?
N5 C12 N2 117.68(17) . . ?
N6 C13 H13A 109.5 . . ?
N6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N6 C14 H14A 109.5 . . ?
N6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N9 C15 N6 122.60(18) . . ?
N9 C15 N7 119.92(19) . . ?
N6 C15 N7 117.35(18) . . ?
N10 C16 N8 122.1(2) . . ?
N10 C16 N7 119.42(18) . . ?
N8 C16 N7 118.47(18) . . ?
C15 N6 C13 121.32(17) . . ?
C15 N6 C14 123.13(17) . . ?
C13 N6 C14 115.35(16) . . ?
C16 N7 C15 124.25(16) . . ?
C16 N7 H70 117.5(13) . . ?
C15 N7 H70 117.8(14) . . ?
C16 N8 H80 123.6(14) . . ?
C16 N8 H81 115.9(15) . . ?
H80 N8 H81 120.5(19) . . ?
C15 N9 H90 126.4(14) . . ?
C15 N9 H91 117.5(13) . . ?
H90 N9 H91 115.2(17) . . ?
C16 N10 H100 121.5(15) . . ?
C16 N10 H101 118.6(13) . . ?
H100 N10 H101 118(2) . . ?
H109 O9 H209 104(3) . . ?
H110 O10 H210 106(2) . . ?

_diffrn_measured_fraction_theta_max .997
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full .997
_refine_diff_density_max         .257
_refine_diff_density_min         -.204
_refine_diff_density_rms         .042
_database_code_depnum_ccdc_archive 'CCDC 1018219'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1d
#==============================================================================

# CHEMICAL DATA 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 N5, 0.5(C4 O4), H2 O'
_chemical_formula_sum            'C6 H14 N5 O3'
_chemical_formula_weight         204.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   7.5760(14)
_cell_length_b                   8.3143(15)
_cell_length_c                   8.5662(16)
_cell_angle_alpha                63.075(2)
_cell_angle_beta                 88.633(3)
_cell_angle_gamma                81.063(3)
_cell_volume                     474.58(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2492
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.52

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             218
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#==============================================================================

# EXPERIMENTAL DATA 

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        'no decay'
_diffrn_reflns_number            5853
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         26.66
_reflns_number_total             2003
_reflns_number_gt                1661
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

#==============================================================================

# REFINEMENT DATA 

_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)+(0.0560P)²+0.0354P] 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         2003
_refine_ls_number_parameters     161
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.14232(15) 0.49071(14) 0.23681(13) 0.0302(3) Uani 1 1 d . . .
O2 O -0.00731(13) 0.19278(12) 0.15276(12) 0.0203(2) Uani 1 1 d . . .
C1 C 0.06438(17) 0.49557(18) 0.10726(17) 0.0175(3) Uani 1 1 d . . .
C2 C -0.00282(17) 0.36074(18) 0.06852(17) 0.0159(3) Uani 1 1 d . . .
N1 N 0.47977(15) 0.74046(15) 0.11287(14) 0.0187(3) Uani 1 1 d . . .
N2 N 0.35547(14) 0.81048(15) 0.32734(14) 0.0178(3) Uani 1 1 d . . .
N3 N 0.20142(18) 0.86873(17) 0.53390(16) 0.0219(3) Uani 1 1 d D . .
H30 H 0.269(2) 0.951(2) 0.526(2) 0.042(5) Uiso 1 1 d D . .
H31 H 0.115(2) 0.856(3) 0.604(2) 0.038(5) Uiso 1 1 d D . .
N4 N 0.21287(16) 0.93718(16) 0.04758(16) 0.0195(3) Uani 1 1 d D . .
H40 H 0.133(2) 0.999(2) 0.086(2) 0.026(4) Uiso 1 1 d D . .
H41 H 0.178(2) 0.914(2) -0.036(2) 0.034(5) Uiso 1 1 d D . .
N5 N 0.07229(18) 0.72624(18) 0.40222(18) 0.0266(3) Uani 1 1 d D . .
H50 H 0.087(2) 0.666(2) 0.340(2) 0.029(4) Uiso 1 1 d D . .
H51 H -0.026(2) 0.733(3) 0.457(3) 0.054(6) Uiso 1 1 d D . .
C3 C 0.6171(2) 0.6019(2) 0.23749(19) 0.0272(4) Uani 1 1 d . . .
H3C H 0.7253 0.6549 0.2317 0.041 Uiso 1 1 calc R . .
H3D H 0.6447 0.4997 0.2086 0.041 Uiso 1 1 calc R . .
H3E H 0.5737 0.5577 0.3562 0.041 Uiso 1 1 calc R . .
C4 C 0.4909(2) 0.7746(2) -0.06924(18) 0.0243(3) Uani 1 1 d . . .
H4C H 0.4205 0.6963 -0.0903 0.036 Uiso 1 1 calc R . .
H4D H 0.6161 0.7474 -0.0934 0.036 Uiso 1 1 calc R . .
H4E H 0.4437 0.9032 -0.1465 0.036 Uiso 1 1 calc R . .
C5 C 0.34571(17) 0.82471(17) 0.16484(17) 0.0160(3) Uani 1 1 d . . .
C6 C 0.20656(18) 0.80547(18) 0.41674(18) 0.0187(3) Uani 1 1 d . . .
O3 O 0.32983(17) 0.18090(16) 0.50233(16) 0.0373(3) Uani 1 1 d D . .
H3A H 0.295(3) 0.279(2) 0.408(2) 0.047(6) Uiso 1 1 d D . .
H3B H 0.427(2) 0.195(3) 0.542(3) 0.059(7) Uiso 1 1 d D . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.2511(17) . ?
O2 C2 1.2542(16) . ?
C1 C2 1.4640(18) 2_565 ?
C1 C2 1.4657(18) . ?
C2 C1 1.4639(18) 2_565 ?
N1 C5 1.3267(17) . ?
N1 C3 1.4544(18) . ?
N1 C4 1.4564(17) . ?
N2 C6 1.3436(17) . ?
N2 C5 1.3454(17) . ?
N3 C6 1.3248(18) . ?
N3 H30 0.891(15) . ?
N3 H31 0.867(14) . ?
N4 C5 1.3422(17) . ?
N4 H40 0.885(14) . ?
N4 H41 0.874(14) . ?
N5 C6 1.3314(18) . ?
N5 H50 0.878(14) . ?
N5 H51 0.880(15) . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
O3 H3A 0.857(15) . ?
O3 H3B 0.867(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 134.68(13) . 2_565 ?
O1 C1 C2 135.09(13) . . ?
C2 C1 C2 90.23(11) 2_565 . ?
O2 C2 C1 135.45(13) . 2_565 ?
O2 C2 C1 134.78(13) . . ?
C1 C2 C1 89.77(11) 2_565 . ?
C5 N1 C3 121.27(12) . . ?
C5 N1 C4 121.71(12) . . ?
C3 N1 C4 116.93(11) . . ?
C6 N2 C5 120.02(11) . . ?
C6 N3 H30 121.4(12) . . ?
C6 N3 H31 121.5(12) . . ?
H30 N3 H31 115.1(18) . . ?
C5 N4 H40 115.0(10) . . ?
C5 N4 H41 121.0(12) . . ?
H40 N4 H41 117.8(16) . . ?
C6 N5 H50 118.0(11) . . ?
C6 N5 H51 119.4(14) . . ?
H50 N5 H51 122.5(18) . . ?
N1 C3 H3C 109.5 . . ?
N1 C3 H3D 109.5 . . ?
H3C C3 H3D 109.5 . . ?
N1 C3 H3E 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
N1 C4 H4C 109.5 . . ?
N1 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
N1 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
N1 C5 N4 118.75(12) . . ?
N1 C5 N2 119.29(12) . . ?
N4 C5 N2 121.59(12) . . ?
N3 C6 N5 119.33(13) . . ?
N3 C6 N2 117.96(13) . . ?
N5 C6 N2 122.47(12) . . ?
H3A O3 H3B 107.1(19) . . ?

_diffrn_measured_fraction_theta_max .997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         .420
_refine_diff_density_min         -.355
_refine_diff_density_rms         .046
_database_code_depnum_ccdc_archive 'CCDC 1018220'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2a
#==============================================================================
# CHEMICAL DATA 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         2(C8H13N5),2(C8H12N5),2(C4HO4),C2H6O,2(C4O4)
_chemical_formula_sum            'C50 H58 N20 O17'
_chemical_formula_weight         1211.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc


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                   13.1608(14)
_cell_length_b                   12.6922(14)
_cell_length_c                   19.7008(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.795(2)
_cell_angle_gamma                90.00
_cell_volume                     2826.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2191
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      21.21

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1268
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        'no decay'
_diffrn_reflns_number            33195
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_sigmaI/netI    0.0930
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         26.41
_reflns_number_total             5795
_reflns_number_gt                3000
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (2001)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

#==============================================================================

# REFINEMENT DATA

_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)+(0.0350P)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         5795
_refine_ls_number_parameters     455
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.929
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.6932(2) 0.89232(19) 0.34801(11) 0.0588(6) Uani 1 1 d D . .
H1 H 0.675(3) 0.9575(16) 0.3497(19) 0.094(15) Uiso 1 1 d D . .
O2 O 0.66810(14) 0.64834(14) 0.38282(9) 0.0368(5) Uani 1 1 d . . .
O3 O 0.62470(14) 0.71783(13) 0.52325(9) 0.0334(4) Uani 1 1 d . . .
O4 O 0.65870(14) 0.96227(14) 0.49364(9) 0.0364(5) Uani 1 1 d . . .
C1 C 0.6793(2) 0.8431(2) 0.40075(14) 0.0343(7) Uani 1 1 d . . .
C2 C 0.6686(2) 0.7350(2) 0.41392(13) 0.0304(6) Uani 1 1 d . . .
C3 C 0.6499(2) 0.7650(2) 0.47882(13) 0.0275(6) Uani 1 1 d . . .
C4 C 0.6630(2) 0.8767(2) 0.46411(13) 0.0294(6) Uani 1 1 d . . .
O5 O 0.38594(15) 0.82963(15) 0.20476(9) 0.0408(5) Uani 1 1 d . . .
O6 O 0.3329(2) 0.58621(15) 0.14610(11) 0.0776(8) Uani 1 1 d . . .
O7 O 0.34028(15) 0.52161(14) 0.30679(9) 0.0414(5) Uani 1 1 d . . .
O8 O 0.39598(14) 0.76149(13) 0.36606(9) 0.0345(4) Uani 1 1 d . . .
C5 C 0.3740(2) 0.7451(2) 0.23225(13) 0.0330(7) Uani 1 1 d . . .
C6 C 0.3507(2) 0.6370(2) 0.20743(15) 0.0439(8) Uani 1 1 d . . .
C7 C 0.3533(2) 0.6054(2) 0.27887(14) 0.0344(7) Uani 1 1 d . . .
C8 C 0.3778(2) 0.7143(2) 0.30534(14) 0.0319(6) Uani 1 1 d . . .
N1 N 0.23221(18) 0.3207(2) 0.28605(11) 0.0345(6) Uani 1 1 d D . .
H10 H 0.267(2) 0.3831(16) 0.2845(16) 0.068(10) Uiso 1 1 d D . .
N2 N 0.28194(17) 0.14577(17) 0.31666(11) 0.0310(5) Uani 1 1 d . . .
N3 N 0.3564(2) 0.0359(2) 0.25472(12) 0.0393(6) Uani 1 1 d D . .
H30 H 0.335(3) 0.0825(19) 0.2133(14) 0.083(11) Uiso 1 1 d D . .
H31 H 0.377(2) -0.0316(15) 0.2471(15) 0.059(10) Uiso 1 1 d D . .
N4 N 0.4038(2) 0.2638(2) 0.29833(13) 0.0381(6) Uani 1 1 d D . .
H40 H 0.399(2) 0.3235(16) 0.2722(14) 0.056(9) Uiso 1 1 d D . .
H41 H 0.456(2) 0.2133(16) 0.3091(15) 0.047(9) Uiso 1 1 d D . .
N5 N 0.35732(18) -0.01583(19) 0.36664(12) 0.0313(5) Uani 1 1 d D . .
H50 H 0.346(2) 0.0031(19) 0.4063(12) 0.050(8) Uiso 1 1 d D . .
H51 H 0.378(2) -0.0847(15) 0.3625(16) 0.061(10) Uiso 1 1 d D . .
C9 C 0.1211(2) 0.3230(2) 0.28230(13) 0.0345(7) Uani 1 1 d . . .
C10 C 0.0836(2) 0.2470(2) 0.31492(13) 0.0355(7) Uani 1 1 d . . .
H10A H 0.1321 0.1879 0.3415 0.043 Uiso 1 1 calc R . .
C11 C -0.0263(2) 0.2585(2) 0.30808(15) 0.0401(7) Uani 1 1 d . . .
H11 H -0.0535 0.2056 0.3291 0.048 Uiso 1 1 calc R . .
C12 C -0.0961(2) 0.3441(2) 0.27180(15) 0.0437(7) Uani 1 1 d . . .
H12 H -0.1706 0.3511 0.2681 0.052 Uiso 1 1 calc R . .
C13 C -0.0570(2) 0.4206(2) 0.24044(16) 0.0474(8) Uani 1 1 d . . .
H13 H -0.1048 0.4805 0.2150 0.057 Uiso 1 1 calc R . .
C14 C 0.0514(2) 0.4102(2) 0.24604(15) 0.0421(7) Uani 1 1 d . . .
H14 H 0.0782 0.4632 0.2248 0.051 Uiso 1 1 calc R . .
C15 C 0.3050(2) 0.2391(2) 0.29912(12) 0.0311(6) Uani 1 1 d . . .
C16 C 0.3342(2) 0.0574(2) 0.31219(13) 0.0309(6) Uani 1 1 d . . .
N6 N 0.26334(18) 0.77945(17) 0.52339(11) 0.0301(5) Uani 1 1 d D . .
H60 H 0.283(2) 0.8291(17) 0.5615(13) 0.058(9) Uiso 1 1 d D . .
N7 N 0.36407(18) 0.67311(17) 0.47882(11) 0.0301(5) Uani 1 1 d D . .
H70 H 0.386(2) 0.6839(19) 0.4454(12) 0.046(8) Uiso 1 1 d D . .
N8 N 0.35226(19) 0.55331(19) 0.56370(12) 0.0316(5) Uani 1 1 d D . .
H80 H 0.364(2) 0.6020(17) 0.6002(13) 0.052(9) Uiso 1 1 d D . .
H81 H 0.340(2) 0.4863(14) 0.5765(14) 0.055(9) Uiso 1 1 d D . .
N9 N 0.43148(19) 0.83748(18) 0.52835(11) 0.0273(5) Uani 1 1 d D . .
H90 H 0.407(2) 0.9040(15) 0.5319(15) 0.059(10) Uiso 1 1 d D . .
H91 H 0.4995(17) 0.8144(19) 0.5316(14) 0.051(9) Uiso 1 1 d D . .
N10 N 0.34715(19) 0.49783(18) 0.45090(12) 0.0317(5) Uani 1 1 d D . .
H100 H 0.3481(18) 0.5150(17) 0.4050(10) 0.039(7) Uiso 1 1 d D . .
H101 H 0.349(2) 0.4265(14) 0.4652(14) 0.053(9) Uiso 1 1 d D . .
C17 C 0.1546(2) 0.7226(2) 0.48859(14) 0.0326(6) Uani 1 1 d . . .
C18 C 0.1074(2) 0.6996(2) 0.53484(14) 0.0397(7) Uani 1 1 d . . .
H18 H 0.1479 0.7196 0.5889 0.048 Uiso 1 1 calc R . .
C19 C 0.0012(2) 0.6474(2) 0.50254(17) 0.0501(8) Uani 1 1 d . . .
H19 H -0.0319 0.6323 0.5344 0.060 Uiso 1 1 calc R . .
C20 C -0.0578(2) 0.6167(2) 0.42458(16) 0.0528(8) Uani 1 1 d . . .
H20 H -0.1302 0.5790 0.4029 0.063 Uiso 1 1 calc R . .
C21 C -0.0107(2) 0.6416(2) 0.37855(16) 0.0509(8) Uani 1 1 d . . .
H21 H -0.0515 0.6215 0.3245 0.061 Uiso 1 1 calc R . .
C22 C 0.0951(2) 0.6953(2) 0.40955(14) 0.0426(7) Uani 1 1 d . . .
H22 H 0.1266 0.7132 0.3771 0.051 Uiso 1 1 calc R . .
C24 C 0.3535(2) 0.5728(2) 0.49868(13) 0.0271(6) Uani 1 1 d . . .
C23 C 0.3519(2) 0.7644(2) 0.51104(12) 0.0256(6) Uani 1 1 d . . .
C30 C 0.0024(8) 0.0131(7) 0.4698(5) 0.050(2) Uiso 0.50 1 d PD A -1
H30A H 0.0674 0.0651 0.4892 0.061 Uiso 0.50 1 calc PR A -1
H30B H 0.0306 -0.0527 0.4580 0.061 Uiso 0.50 1 calc PR A -1
C31 C -0.0232(13) -0.0106(11) 0.5398(8) 0.142(6) Uiso 0.50 1 d PD A -1
H31A H 0.0519 -0.0225 0.5892 0.212 Uiso 0.50 1 calc PR A -1
H31B H -0.0730 -0.0734 0.5268 0.212 Uiso 0.50 1 calc PR A -1
H31C H -0.0639 0.0498 0.5462 0.212 Uiso 0.50 1 calc PR A -1
O30 O -0.0925(5) 0.0509(5) 0.4000(3) 0.120(2) Uiso 0.50 1 d P A -1
H30C H -0.1448 0.0041 0.3795 0.181 Uiso 0.50 1 calc PR A -1


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.303(3) . ?
O1 H1 0.867(18) . ?
O2 C2 1.257(3) . ?
O3 C3 1.238(2) . ?
O4 C4 1.247(3) . ?
C1 C2 1.417(3) . ?
C1 C4 1.436(3) . ?
C1 C3 2.027(3) . ?
C2 C3 1.471(3) . ?
C3 C4 1.474(3) . ?
O5 C5 1.247(3) . ?
O6 C6 1.281(3) . ?
O7 C7 1.249(3) . ?
O8 C8 1.247(3) . ?
C5 C6 1.435(4) . ?
C5 C8 1.468(3) . ?
C6 C7 1.447(3) . ?
C6 C8 2.026(4) . ?
C7 C8 1.454(4) . ?
N1 C15 1.343(3) . ?
N1 C9 1.426(3) . ?
N1 H10 0.924(17) . ?
N2 C15 1.312(3) . ?
N2 C16 1.342(3) . ?
N3 C16 1.335(3) . ?
N3 H30 0.927(17) . ?
N3 H31 0.935(16) . ?
N4 C15 1.346(3) . ?
N4 H40 0.899(16) . ?
N4 H41 0.882(16) . ?
N5 C16 1.331(3) . ?
N5 H50 0.903(16) . ?
N5 H51 0.932(16) . ?
C9 C14 1.380(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.391(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.365(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
N6 C23 1.321(3) . ?
N6 C17 1.426(3) . ?
N6 H60 0.911(16) . ?
N7 C24 1.360(3) . ?
N7 C23 1.369(3) . ?
N7 H70 0.858(16) . ?
N8 C24 1.313(3) . ?
N8 H80 0.898(16) . ?
N8 H81 0.925(16) . ?
N9 C23 1.306(3) . ?
N9 H90 0.918(16) . ?
N9 H91 0.913(16) . ?
N10 C24 1.311(3) . ?
N10 H100 0.937(15) . ?
N10 H101 0.945(16) . ?
C17 C18 1.372(3) . ?
C17 C22 1.382(3) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C30 O30 1.386(9) . ?
C30 C31 1.605(8) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O30 H30C 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
C1 O1 H1 106(2) . . ?
O1 C1 C2 132.7(2) . . ?
O1 C1 C4 134.1(3) . . ?
C2 C1 C4 93.2(2) . . ?
O1 C1 C3 177.4(2) . . ?
C2 C1 C3 46.52(13) . . ?
C4 C1 C3 46.64(14) . . ?
O2 C2 C1 137.2(2) . . ?
O2 C2 C3 133.6(2) . . ?
C1 C2 C3 89.13(19) . . ?
O3 C3 C2 135.6(2) . . ?
O3 C3 C4 134.8(2) . . ?
C2 C3 C4 89.43(19) . . ?
O3 C3 C1 176.1(2) . . ?
C2 C3 C1 44.35(13) . . ?
C4 C3 C1 45.08(13) . . ?
O4 C4 C1 136.6(2) . . ?
O4 C4 C3 135.1(2) . . ?
C1 C4 C3 88.3(2) . . ?
O5 C5 C6 136.6(2) . . ?
O5 C5 C8 134.9(3) . . ?
C6 C5 C8 88.5(2) . . ?
O6 C6 C5 135.0(2) . . ?
O6 C6 C7 132.8(3) . . ?
C5 C6 C7 92.2(2) . . ?
O6 C6 C8 178.6(3) . . ?
C5 C6 C8 46.40(14) . . ?
C7 C6 C8 45.84(14) . . ?
O7 C7 C6 136.4(3) . . ?
O7 C7 C8 135.0(2) . . ?
C6 C7 C8 88.6(2) . . ?
O8 C8 C7 134.3(2) . . ?
O8 C8 C5 135.0(3) . . ?
C7 C8 C5 90.7(2) . . ?
O8 C8 C6 179.2(2) . . ?
C7 C8 C6 45.56(14) . . ?
C5 C8 C6 45.10(14) . . ?
C15 N1 C9 129.6(2) . . ?
C15 N1 H10 110.5(18) . . ?
C9 N1 H10 119.6(18) . . ?
C15 N2 C16 122.8(2) . . ?
C16 N3 H30 120.8(18) . . ?
C16 N3 H31 122.2(16) . . ?
H30 N3 H31 115(2) . . ?
C15 N4 H40 114.7(17) . . ?
C15 N4 H41 117.7(17) . . ?
H40 N4 H41 125(2) . . ?
C16 N5 H50 116.2(16) . . ?
C16 N5 H51 122.8(17) . . ?
H50 N5 H51 121(2) . . ?
C14 C9 C10 119.9(2) . . ?
C14 C9 N1 115.9(2) . . ?
C10 C9 N1 124.2(2) . . ?
C9 C10 C11 118.9(2) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
N2 C15 N1 120.6(2) . . ?
N2 C15 N4 124.7(2) . . ?
N1 C15 N4 114.6(3) . . ?
N5 C16 N3 118.8(3) . . ?
N5 C16 N2 116.4(2) . . ?
N3 C16 N2 124.7(2) . . ?
C23 N6 C17 127.0(2) . . ?
C23 N6 H60 110.6(16) . . ?
C17 N6 H60 122.3(16) . . ?
C24 N7 C23 127.3(2) . . ?
C24 N7 H70 119.7(17) . . ?
C23 N7 H70 112.8(17) . . ?
C24 N8 H80 124.5(17) . . ?
C24 N8 H81 122.1(16) . . ?
H80 N8 H81 113(2) . . ?
C23 N9 H90 114.2(17) . . ?
C23 N9 H91 114.7(17) . . ?
H90 N9 H91 131(2) . . ?
C24 N10 H100 119.8(14) . . ?
C24 N10 H101 120.0(15) . . ?
H100 N10 H101 120(2) . . ?
C18 C17 C22 120.5(2) . . ?
C18 C17 N6 118.2(2) . . ?
C22 C17 N6 121.2(2) . . ?
C17 C18 C19 119.6(2) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 119.0(3) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C17 118.9(2) . . ?
C21 C22 H22 120.6 . . ?
C17 C22 H22 120.6 . . ?
N10 C24 N8 122.4(2) . . ?
N10 C24 N7 116.8(2) . . ?
N8 C24 N7 120.7(2) . . ?
N9 C23 N6 120.9(2) . . ?
N9 C23 N7 117.0(2) . . ?
N6 C23 N7 122.1(2) . . ?
O30 C30 C31 116.0(6) . . ?
O30 C30 H30A 108.3 . . ?
C31 C30 H30A 108.3 . . ?
O30 C30 H30B 108.3 . . ?
C31 C30 H30B 108.3 . . ?
H30A C30 H30B 107.4 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 O30 H30C 109.5 . . ?

_diffrn_measured_fraction_theta_max .998
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full .998
_refine_diff_density_max         .454
_refine_diff_density_min         -.294
_refine_diff_density_rms         .049
_database_code_depnum_ccdc_archive 'CCDC 1018221'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2b
#==============================================================================
# CHEMICAL DATA 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H12 N5), C4 O4'
_chemical_formula_sum            'C20 H24 N10 O4'
_chemical_formula_weight         468.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   8.9093(16)
_cell_length_b                   10.772(2)
_cell_length_c                   12.425(2)
_cell_angle_alpha                71.502(3)
_cell_angle_beta                 74.311(3)
_cell_angle_gamma                80.732(3)
_cell_volume                     1085.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1908
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      23.09

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        'no decay'
_diffrn_reflns_number            13257
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0787
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         26.44
_reflns_number_total             4464
_reflns_number_gt                3082
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

#==============================================================================

# REFINEMENT DATA

_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)+(0.0235P)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         4464
_refine_ls_number_parameters     363
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.924
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.08393(14) 0.72348(12) 0.86334(11) 0.0181(3) Uani 1 1 d . . .
O2 O 0.27268(14) 0.96656(12) 0.83388(11) 0.0208(3) Uani 1 1 d . . .
O3 O 0.57652(14) 0.76388(12) 0.88702(11) 0.0181(3) Uani 1 1 d . . .
O4 O 0.39990(14) 0.52593(12) 0.88792(11) 0.0181(3) Uani 1 1 d . . .
C1 C 0.2223(2) 0.73458(18) 0.86234(15) 0.0146(4) Uani 1 1 d . . .
C2 C 0.3066(2) 0.84448(18) 0.85242(16) 0.0157(4) Uani 1 1 d . . .
C3 C 0.4445(2) 0.75453(18) 0.87254(16) 0.0150(4) Uani 1 1 d . . .
C4 C 0.3632(2) 0.64562(18) 0.87613(15) 0.0144(4) Uani 1 1 d . . .
N1 N -0.24778(19) 0.61055(17) 0.26289(14) 0.0212(4) Uani 1 1 d D . .
H100 H -0.3333(19) 0.6124(19) 0.2377(16) 0.027(6) Uiso 1 1 d D . .
N2 N 0.02221(17) 0.61296(14) 0.20387(13) 0.0147(4) Uani 1 1 d . . .
N3 N 0.1556(2) 0.42250(16) 0.15694(14) 0.0164(4) Uani 1 1 d D . .
H130 H 0.0635(19) 0.3947(19) 0.1678(17) 0.029(6) Uiso 1 1 d D . .
H131 H 0.2495(19) 0.3778(18) 0.1373(17) 0.035(7) Uiso 1 1 d D . .
N4 N -0.1265(2) 0.58782(16) 0.08398(14) 0.0168(4) Uani 1 1 d D . .
H140 H -0.043(2) 0.600(2) 0.0225(16) 0.042(7) Uiso 1 1 d D . .
H141 H -0.2199(19) 0.5614(19) 0.0814(17) 0.032(6) Uiso 1 1 d D . .
N5 N 0.28898(19) 0.59123(17) 0.14691(14) 0.0164(4) Uani 1 1 d D . .
H150 H 0.3843(19) 0.5436(17) 0.1283(16) 0.028(6) Uiso 1 1 d D . .
H151 H 0.282(2) 0.6682(15) 0.1530(16) 0.023(6) Uiso 1 1 d D . .
C5 C -0.4313(2) 0.64851(19) 0.42969(17) 0.0235(5) Uani 1 1 d . . .
H5 H -0.5098 0.6589 0.3881 0.028 Uiso 1 1 calc R . .
C6 C -0.4728(3) 0.6615(2) 0.54104(18) 0.0296(5) Uani 1 1 d . . .
H6 H -0.5792 0.6816 0.5756 0.036 Uiso 1 1 calc R . .
C7 C -0.3598(3) 0.6452(2) 0.60211(18) 0.0296(5) Uani 1 1 d . . .
H7 H -0.3877 0.6534 0.6791 0.036 Uiso 1 1 calc R . .
C8 C -0.2067(3) 0.6171(2) 0.55081(18) 0.0312(6) Uani 1 1 d . . .
H8 H -0.1289 0.6056 0.5933 0.037 Uiso 1 1 calc R . .
C9 C -0.1626(2) 0.6051(2) 0.43906(18) 0.0287(5) Uani 1 1 d . . .
H9 H -0.0558 0.5865 0.4045 0.034 Uiso 1 1 calc R . .
C10 C -0.2769(2) 0.62061(19) 0.37794(16) 0.0193(5) Uani 1 1 d . . .
C11 C -0.1118(2) 0.59982(17) 0.18386(16) 0.0147(4) Uani 1 1 d . . .
C12 C 0.1544(2) 0.54305(18) 0.16598(15) 0.0139(4) Uani 1 1 d . . .
N6 N 0.56177(18) 1.06822(15) 0.75072(14) 0.0166(4) Uani 1 1 d D . .
H160 H 0.4611(19) 1.0420(19) 0.7641(17) 0.037(6) Uiso 1 1 d D . .
N7 N 0.71176(17) 1.13895(15) 0.84913(14) 0.0169(4) Uani 1 1 d . . .
N8 N 0.8341(2) 0.92642(16) 0.85300(15) 0.0184(4) Uani 1 1 d D . .
H180 H 0.925(2) 0.8696(18) 0.8544(18) 0.036(6) Uiso 1 1 d D . .
H181 H 0.747(2) 0.891(2) 0.8571(19) 0.043(7) Uiso 1 1 d D . .
N9 N 0.44534(19) 1.15272(17) 0.90253(15) 0.0194(4) Uani 1 1 d D . .
H190 H 0.448(3) 1.173(2) 0.9675(15) 0.050(8) Uiso 1 1 d D . .
H191 H 0.349(2) 1.140(2) 0.8979(18) 0.040(7) Uiso 1 1 d D . .
N10 N 0.9745(2) 1.09798(17) 0.82718(16) 0.0234(4) Uani 1 1 d D . .
H200 H 0.975(3) 1.1889(16) 0.815(2) 0.063(8) Uiso 1 1 d D . .
H201 H 1.0627(18) 1.0469(17) 0.8305(16) 0.018(5) Uiso 1 1 d D . .
C13 C 0.6467(2) 0.9821(2) 0.58712(18) 0.0257(5) Uani 1 1 d . . .
H13 H 0.5695 0.9209 0.6249 0.031 Uiso 1 1 calc R . .
C14 C 0.7364(3) 0.9851(2) 0.47668(18) 0.0328(6) Uani 1 1 d . . .
H14 H 0.7204 0.9264 0.4384 0.039 Uiso 1 1 calc R . .
C15 C 0.8485(3) 1.0727(2) 0.42231(19) 0.0336(6) Uani 1 1 d . . .
H15 H 0.9099 1.0750 0.3463 0.040 Uiso 1 1 calc R . .
C16 C 0.8720(2) 1.1573(2) 0.47804(18) 0.0320(6) Uani 1 1 d . . .
H16 H 0.9506 1.2171 0.4402 0.038 Uiso 1 1 calc R . .
C17 C 0.7829(2) 1.1566(2) 0.58807(17) 0.0242(5) Uani 1 1 d . . .
H17 H 0.7994 1.2157 0.6257 0.029 Uiso 1 1 calc R . .
C18 C 0.6690(2) 1.06816(19) 0.64291(16) 0.0178(4) Uani 1 1 d . . .
C19 C 0.5779(2) 1.11653(18) 0.83403(16) 0.0154(4) Uani 1 1 d . . .
C20 C 0.8388(2) 1.05349(18) 0.84084(16) 0.0168(4) Uani 1 1 d . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.254(2) . ?
O2 C2 1.261(2) . ?
O3 C3 1.261(2) . ?
O4 C4 1.249(2) . ?
C1 C2 1.458(2) . ?
C1 C4 1.466(3) . ?
C2 C3 1.463(2) . ?
C3 C4 1.458(2) . ?
N1 C11 1.352(2) . ?
N1 C10 1.418(2) . ?
N1 H100 0.894(14) . ?
N2 C11 1.321(2) . ?
N2 C12 1.347(2) . ?
N3 C12 1.337(2) . ?
N3 H130 0.880(14) . ?
N3 H131 0.908(15) . ?
N4 C11 1.330(2) . ?
N4 H140 0.902(15) . ?
N4 H141 0.934(14) . ?
N5 C12 1.316(2) . ?
N5 H150 0.930(14) . ?
N5 H151 0.847(14) . ?
C5 C6 1.378(3) . ?
C5 C10 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.371(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
N6 C19 1.345(2) . ?
N6 C18 1.419(2) . ?
N6 H160 0.940(14) . ?
N7 C19 1.326(2) . ?
N7 C20 1.342(2) . ?
N8 C20 1.335(2) . ?
N8 H180 0.932(15) . ?
N8 H181 0.896(15) . ?
N9 C19 1.338(2) . ?
N9 H190 0.909(15) . ?
N9 H191 0.915(15) . ?
N10 C20 1.321(2) . ?
N10 H200 0.944(16) . ?
N10 H201 0.886(14) . ?
C13 C14 1.382(3) . ?
C13 C18 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 133.82(17) . . ?
O1 C1 C4 136.28(17) . . ?
C2 C1 C4 89.84(14) . . ?
O2 C2 C1 134.34(17) . . ?
O2 C2 C3 135.57(17) . . ?
C1 C2 C3 90.09(15) . . ?
O3 C3 C4 134.23(17) . . ?
O3 C3 C2 135.73(17) . . ?
C4 C3 C2 89.96(15) . . ?
O4 C4 C3 134.37(17) . . ?
O4 C4 C1 135.66(17) . . ?
C3 C4 C1 89.96(15) . . ?
C11 N1 C10 130.81(17) . . ?
C11 N1 H100 114.2(13) . . ?
C10 N1 H100 115.0(13) . . ?
C11 N2 C12 120.81(16) . . ?
C12 N3 H130 116.0(13) . . ?
C12 N3 H131 118.4(13) . . ?
H130 N3 H131 125.5(18) . . ?
C11 N4 H140 118.5(14) . . ?
C11 N4 H141 119.0(12) . . ?
H140 N4 H141 122.3(18) . . ?
C12 N5 H150 122.0(12) . . ?
C12 N5 H151 115.0(13) . . ?
H150 N5 H151 123.0(18) . . ?
C6 C5 C10 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C5 C10 C9 119.51(19) . . ?
C5 C10 N1 115.81(18) . . ?
C9 C10 N1 124.68(18) . . ?
N2 C11 N4 124.13(18) . . ?
N2 C11 N1 120.35(17) . . ?
N4 C11 N1 115.24(17) . . ?
N5 C12 N3 118.60(18) . . ?
N5 C12 N2 118.17(17) . . ?
N3 C12 N2 122.96(17) . . ?
C19 N6 C18 127.99(17) . . ?
C19 N6 H160 113.1(12) . . ?
C18 N6 H160 118.4(13) . . ?
C19 N7 C20 121.76(17) . . ?
C20 N8 H180 120.4(13) . . ?
C20 N8 H181 123.4(14) . . ?
H180 N8 H181 116.2(18) . . ?
C19 N9 H190 120.0(15) . . ?
C19 N9 H191 122.8(13) . . ?
H190 N9 H191 115.6(19) . . ?
C20 N10 H200 117.1(15) . . ?
C20 N10 H201 123.5(12) . . ?
H200 N10 H201 119.4(19) . . ?
C14 C13 C18 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C18 C13 H13 119.9 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 119.1(2) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 119.82(19) . . ?
C13 C18 N6 116.70(17) . . ?
C17 C18 N6 123.23(18) . . ?
N7 C19 N9 117.64(18) . . ?
N7 C19 N6 126.02(18) . . ?
N9 C19 N6 116.20(18) . . ?
N10 C20 N8 118.95(18) . . ?
N10 C20 N7 116.88(18) . . ?
N8 C20 N7 124.02(18) . . ?

_diffrn_measured_fraction_theta_max .998
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full .998
_refine_diff_density_max         .206
_refine_diff_density_min         -.272
_refine_diff_density_rms         .055
_database_code_depnum_ccdc_archive 'CCDC 1018222'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3a
#==============================================================================
# CHEMICAL DATA 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H15 N5, C4 O4, H2 O'
_chemical_formula_sum            'C13 H17 N5 O5'
_chemical_formula_weight         323.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc

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                   8.2558(12)
_cell_length_b                   14.578(2)
_cell_length_c                   13.1414(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.833(2)
_cell_angle_gamma                90.00
_cell_volume                     1542.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2364
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      22.91

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        'no decay'
_diffrn_reflns_number            19615
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3538
_reflns_number_gt                2404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

#==============================================================================

# REFINEMENT DATA

_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)+(0.0394P)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         3538
_refine_ls_number_parameters     249
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.893
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.77264(13) 0.04240(8) 0.55531(9) 0.0183(3) Uani 1 1 d . . .
O2 O 0.42185(14) 0.09423(8) 0.62051(9) 0.0196(3) Uani 1 1 d . . .
C1 C 0.6220(2) 0.01922(11) 0.52549(12) 0.0152(4) Uani 1 1 d . . .
C2 C 0.4658(2) 0.04285(11) 0.55494(12) 0.0153(4) Uani 1 1 d . . .
O3 O 0.95848(16) 0.05798(8) 0.15377(9) 0.0250(3) Uani 1 1 d . . .
O4 O 1.04073(16) 0.14518(8) -0.05638(9) 0.0267(3) Uani 1 1 d . . .
C3 C 0.9811(2) 0.02653(11) 0.06920(13) 0.0189(4) Uani 1 1 d . . .
C4 C 1.0184(2) 0.06569(11) -0.02537(13) 0.0188(4) Uani 1 1 d . . .
N2 N 0.95859(17) 0.23568(10) 0.19288(11) 0.0165(3) Uani 1 1 d D . .
H120 H 0.974(2) 0.1763(10) 0.1770(15) 0.035(6) Uiso 1 1 d D . .
N1 N 0.75668(18) 0.18644(10) 0.27294(12) 0.0212(3) Uani 1 1 d D . .
H110 H 0.821(2) 0.1401(11) 0.2968(14) 0.033(6) Uiso 1 1 d D . .
N4 N 0.73861(19) 0.33271(10) 0.20455(12) 0.0227(4) Uani 1 1 d D . .
H140 H 0.634(2) 0.3399(13) 0.2200(15) 0.035(6) Uiso 1 1 d D . .
H141 H 0.775(2) 0.3727(12) 0.1627(14) 0.038(6) Uiso 1 1 d D . .
N3 N 1.13897(19) 0.28929(10) 0.09531(12) 0.0195(3) Uani 1 1 d D . .
H130 H 1.223(2) 0.3266(13) 0.0893(17) 0.047(7) Uiso 1 1 d D . .
H131 H 1.101(3) 0.2447(13) 0.0469(15) 0.053(7) Uiso 1 1 d D . .
N5 N 1.09636(18) 0.37332(10) 0.23523(12) 0.0186(3) Uani 1 1 d D . .
H150 H 1.065(2) 0.3750(13) 0.2971(13) 0.037(6) Uiso 1 1 d D . .
H151 H 1.137(2) 0.4239(11) 0.2132(14) 0.024(5) Uiso 1 1 d D . .
C12 C 0.8145(2) 0.25387(11) 0.22492(13) 0.0171(4) Uani 1 1 d . . .
C11 C 0.6006(2) 0.18951(12) 0.30403(14) 0.0204(4) Uani 1 1 d . . .
C6 C 0.4757(2) 0.12928(12) 0.25726(14) 0.0237(4) Uani 1 1 d . . .
C7 C 0.3278(2) 0.13234(14) 0.29194(15) 0.0302(5) Uani 1 1 d . . .
H7 H 0.2398 0.0918 0.2623 0.036 Uiso 1 1 calc R . .
C8 C 0.3070(2) 0.19276(14) 0.36788(16) 0.0324(5) Uani 1 1 d . . .
H8 H 0.2045 0.1940 0.3894 0.039 Uiso 1 1 calc R . .
C9 C 0.4322(2) 0.25150(14) 0.41338(16) 0.0334(5) Uani 1 1 d . . .
H9 H 0.4168 0.2931 0.4661 0.040 Uiso 1 1 calc R . .
C10 C 0.5806(2) 0.24950(13) 0.38177(15) 0.0288(5) Uani 1 1 d . . .
H10 H 0.6688 0.2892 0.4133 0.035 Uiso 1 1 calc R . .
C5 C 0.4971(3) 0.06301(14) 0.17432(16) 0.0394(5) Uani 1 1 d . . .
H5C H 0.5591 0.0926 0.1278 0.059 Uiso 1 1 calc R . .
H5D H 0.3878 0.0439 0.1340 0.059 Uiso 1 1 calc R . .
H5E H 0.5585 0.0091 0.2068 0.059 Uiso 1 1 calc R . .
C13 C 1.0666(2) 0.30190(11) 0.17351(13) 0.0159(4) Uani 1 1 d . . .
O5 O 0.91643(17) 0.04298(9) 0.38269(10) 0.0229(3) Uani 1 1 d D . .
H5A H 0.875(2) 0.0434(14) 0.4354(14) 0.043(7) Uiso 1 1 d D . .
H5B H 1.019(2) 0.0264(16) 0.3963(17) 0.060(8) Uiso 1 1 d D . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.2642(19) . ?
O2 C2 1.2547(19) . ?
C1 C2 1.456(2) 3_656 ?
C1 C2 1.467(2) . ?
C2 C1 1.456(2) 3_656 ?
O3 C3 1.2542(19) . ?
O4 C4 1.2554(19) . ?
C3 C4 1.461(2) . ?
C3 C4 1.463(2) 3_755 ?
C4 C3 1.463(2) 3_755 ?
N2 C12 1.373(2) . ?
N2 C13 1.376(2) . ?
N2 H120 0.906(14) . ?
N1 C12 1.314(2) . ?
N1 C11 1.437(2) . ?
N1 H110 0.873(14) . ?
N4 C12 1.308(2) . ?
N4 H140 0.933(14) . ?
N4 H141 0.898(14) . ?
N3 C13 1.311(2) . ?
N3 H130 0.901(15) . ?
N3 H131 0.915(15) . ?
N5 C13 1.309(2) . ?
N5 H150 0.906(15) . ?
N5 H151 0.885(14) . ?
C11 C10 1.382(3) . ?
C11 C6 1.389(2) . ?
C6 C7 1.396(2) . ?
C6 C5 1.496(3) . ?
C7 C8 1.370(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C5 H5C 0.9800 . ?
C5 H5D 0.9800 . ?
C5 H5E 0.9800 . ?
O5 H5A 0.839(15) . ?
O5 H5B 0.859(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 133.47(15) . 3_656 ?
O1 C1 C2 135.82(16) . . ?
C2 C1 C2 90.71(13) 3_656 . ?
O2 C2 C1 134.11(15) . 3_656 ?
O2 C2 C1 136.60(16) . . ?
C1 C2 C1 89.29(13) 3_656 . ?
O3 C3 C4 135.40(16) . . ?
O3 C3 C4 134.33(16) . 3_755 ?
C4 C3 C4 90.28(13) . 3_755 ?
O4 C4 C3 135.28(16) . . ?
O4 C4 C3 134.99(16) . 3_755 ?
C3 C4 C3 89.72(13) . 3_755 ?
C12 N2 C13 124.23(14) . . ?
C12 N2 H120 115.3(12) . . ?
C13 N2 H120 120.0(12) . . ?
C12 N1 C11 123.89(15) . . ?
C12 N1 H110 119.7(13) . . ?
C11 N1 H110 115.7(13) . . ?
C12 N4 H140 118.5(12) . . ?
C12 N4 H141 119.1(12) . . ?
H140 N4 H141 120.7(17) . . ?
C13 N3 H130 118.7(14) . . ?
C13 N3 H131 119.9(14) . . ?
H130 N3 H131 121.4(19) . . ?
C13 N5 H150 121.7(12) . . ?
C13 N5 H151 119.5(12) . . ?
H150 N5 H151 118.3(17) . . ?
N4 C12 N1 123.19(16) . . ?
N4 C12 N2 121.01(15) . . ?
N1 C12 N2 115.76(15) . . ?
C10 C11 C6 121.88(17) . . ?
C10 C11 N1 119.46(16) . . ?
C6 C11 N1 118.62(16) . . ?
C11 C6 C7 116.90(18) . . ?
C11 C6 C5 122.28(17) . . ?
C7 C6 C5 120.82(18) . . ?
C8 C7 C6 121.24(19) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.93(18) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 119.29(19) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 119.75(19) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C6 C5 H5C 109.5 . . ?
C6 C5 H5D 109.5 . . ?
H5C C5 H5D 109.5 . . ?
C6 C5 H5E 109.5 . . ?
H5C C5 H5E 109.5 . . ?
H5D C5 H5E 109.5 . . ?
N5 C13 N3 122.79(16) . . ?
N5 C13 N2 118.92(15) . . ?
N3 C13 N2 118.26(15) . . ?
H5A O5 H5B 113(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         .505
_refine_diff_density_min         -.254
_refine_diff_density_rms         .054
_database_code_depnum_ccdc_archive 'CCDC 1018223'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3b
#==============================================================================
# CHEMICAL DATA 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H15 N5, C4 O4, H2 O'
_chemical_formula_sum            'C13 H17 N5 O5'
_chemical_formula_weight         323.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   8.0245(7)
_cell_length_b                   13.0557(11)
_cell_length_c                   22.2369(19)
_cell_angle_alpha                87.683(2)
_cell_angle_beta                 82.848(2)
_cell_angle_gamma                73.025(2)
_cell_volume                     2210.8(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3853
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.22

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1020
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        'no decay'
_diffrn_reflns_number            26487
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_sigmaI/netI    0.0942
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         26.38
_reflns_number_total             9008
_reflns_number_gt                5975
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (2001)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

#==============================================================================

# REFINEMENT DATA

_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)+(0.0300P)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         9008
_refine_ls_number_parameters     745
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.4448(3) 0.99102(19) 0.11582(10) 0.0141(5) Uani 1 1 d . . .
C2 C 0.6030(3) 1.02591(18) 0.10044(11) 0.0137(5) Uani 1 1 d . . .
C3 C 0.6710(3) 0.97470(18) 0.15532(10) 0.0141(5) Uani 1 1 d . . .
C4 C 0.5154(3) 0.93742(18) 0.17002(10) 0.0140(5) Uani 1 1 d . . .
O1 O 0.3059(2) 1.00163(13) 0.09297(7) 0.0170(4) Uani 1 1 d . . .
O2 O 0.6608(2) 1.07533(13) 0.05695(7) 0.0188(4) Uani 1 1 d . . .
O3 O 0.8091(2) 0.96550(13) 0.17929(7) 0.0161(4) Uani 1 1 d . . .
O4 O 0.4611(2) 0.88057(13) 0.21005(7) 0.0182(4) Uani 1 1 d . . .
C5 C 0.6326(3) 0.47429(19) 0.48619(10) 0.0143(5) Uani 1 1 d . . .
C6 C 0.4802(3) 0.44278(18) 0.47302(10) 0.0141(5) Uani 1 1 d . . .
O5 O 0.7954(2) 0.44237(13) 0.46942(7) 0.0166(4) Uani 1 1 d . . .
O6 O 0.4551(2) 0.37346(13) 0.44088(7) 0.0186(4) Uani 1 1 d . . .
C7 C 0.0460(3) 0.54746(19) 0.23221(11) 0.0161(5) Uani 1 1 d . . .
C8 C 0.0310(3) 0.45469(19) 0.20069(11) 0.0156(5) Uani 1 1 d . . .
C9 C -0.0349(3) 0.52410(19) 0.15032(11) 0.0155(5) Uani 1 1 d . . .
C10 C -0.0178(3) 0.61518(19) 0.18093(11) 0.0150(5) Uani 1 1 d . . .
O7 O 0.0939(2) 0.56291(13) 0.28113(7) 0.0232(4) Uani 1 1 d . . .
O8 O 0.0673(2) 0.35584(13) 0.21165(7) 0.0194(4) Uani 1 1 d . . .
O9 O -0.0830(2) 0.51175(13) 0.09997(7) 0.0191(4) Uani 1 1 d . . .
O10 O -0.0397(2) 0.71257(13) 0.16763(7) 0.0185(4) Uani 1 1 d . . .
C11 C -0.0341(3) -0.05829(18) 0.47875(11) 0.0151(5) Uani 1 1 d . . .
C12 C 0.0516(3) 0.02386(18) 0.45868(11) 0.0145(5) Uani 1 1 d . . .
O11 O -0.0746(2) -0.12959(13) 0.45306(7) 0.0195(4) Uani 1 1 d . . .
O12 O 0.1146(2) 0.05183(13) 0.40850(7) 0.0201(4) Uani 1 1 d . . .
C13 C 0.4842(3) 0.6271(2) 0.14676(11) 0.0249(6) Uani 1 1 d . . .
H13A H 0.5875 0.5665 0.1522 0.037 Uiso 1 1 calc R . .
H13B H 0.3828 0.6179 0.1735 0.037 Uiso 1 1 calc R . .
H13C H 0.5067 0.6938 0.1569 0.037 Uiso 1 1 calc R . .
C14 C 0.4471(3) 0.63157(18) 0.08236(11) 0.0177(6) Uani 1 1 d . . .
C15 C 0.3107(3) 0.59734(19) 0.06635(12) 0.0226(6) Uani 1 1 d . . .
H15 H 0.2393 0.5720 0.0972 0.027 Uiso 1 1 calc R . .
C16 C 0.2752(3) 0.5989(2) 0.00731(13) 0.0250(6) Uani 1 1 d . . .
H16 H 0.1800 0.5755 -0.0021 0.030 Uiso 1 1 calc R . .
C17 C 0.3783(3) 0.63438(19) -0.03811(12) 0.0222(6) Uani 1 1 d . . .
H17 H 0.3533 0.6367 -0.0789 0.027 Uiso 1 1 calc R . .
C18 C 0.5182(3) 0.66661(19) -0.02416(11) 0.0190(6) Uani 1 1 d . . .
H18 H 0.5917 0.6893 -0.0554 0.023 Uiso 1 1 calc R . .
C19 C 0.5508(3) 0.66575(18) 0.03540(11) 0.0159(5) Uani 1 1 d . . .
C20 C 0.7471(3) 0.77810(19) 0.03280(10) 0.0136(5) Uani 1 1 d . . .
C21 C 1.0037(3) 0.84530(18) 0.03228(11) 0.0140(5) Uani 1 1 d . . .
N1 N 0.7025(3) 0.69106(16) 0.05008(9) 0.0154(5) Uani 1 1 d D . .
H101 H 0.781(3) 0.6408(16) 0.0678(10) 0.018(7) Uiso 1 1 d D . .
N2 N 0.8916(2) 0.78837(16) 0.05624(9) 0.0136(4) Uani 1 1 d D . .
H102 H 0.909(3) 0.7598(18) 0.0932(8) 0.017(7) Uiso 1 1 d D . .
N3 N 1.0778(3) 0.88358(17) 0.07239(10) 0.0181(5) Uani 1 1 d D . .
H103 H 1.027(3) 0.889(2) 0.1105(8) 0.035(9) Uiso 1 1 d D . .
H203 H 1.165(3) 0.9139(19) 0.0609(11) 0.030(8) Uiso 1 1 d D . .
N4 N 0.6554(3) 0.85383(16) 0.00002(9) 0.0142(5) Uani 1 1 d D . .
H104 H 0.692(3) 0.9102(17) -0.0141(11) 0.035(8) Uiso 1 1 d D . .
H204 H 0.555(3) 0.848(2) -0.0142(12) 0.045(9) Uiso 1 1 d D . .
N5 N 1.0359(3) 0.85695(16) -0.02613(9) 0.0156(5) Uani 1 1 d D . .
H105 H 1.119(3) 0.8890(19) -0.0402(11) 0.028(8) Uiso 1 1 d D . .
H205 H 1.009(4) 0.812(2) -0.0497(11) 0.047(10) Uiso 1 1 d D . .
C22 C -0.3686(4) 0.3031(2) 0.20733(13) 0.0395(8) Uani 1 1 d . . .
H22A H -0.3425 0.3603 0.2282 0.059 Uiso 1 1 calc R . .
H22B H -0.4732 0.3334 0.1867 0.059 Uiso 1 1 calc R . .
H22C H -0.2688 0.2694 0.1775 0.059 Uiso 1 1 calc R . .
C23 C -0.4008(3) 0.2217(2) 0.25221(12) 0.0239(6) Uani 1 1 d . . .
C24 C -0.5476(3) 0.1848(2) 0.25315(13) 0.0293(7) Uani 1 1 d . . .
H24 H -0.6269 0.2107 0.2239 0.035 Uiso 1 1 calc R . .
C25 C -0.5794(4) 0.1115(2) 0.29589(14) 0.0318(7) Uani 1 1 d . . .
H25 H -0.6805 0.0877 0.2957 0.038 Uiso 1 1 calc R . .
C26 C -0.4676(4) 0.0721(2) 0.33896(14) 0.0334(7) Uani 1 1 d . . .
H26 H -0.4920 0.0227 0.3688 0.040 Uiso 1 1 calc R . .
C27 C -0.3203(3) 0.1053(2) 0.33810(12) 0.0260(6) Uani 1 1 d . . .
H27 H -0.2401 0.0775 0.3669 0.031 Uiso 1 1 calc R . .
C28 C -0.2886(3) 0.1796(2) 0.29513(11) 0.0191(6) Uani 1 1 d . . .
C29 C -0.0957(3) 0.26234(19) 0.33830(11) 0.0158(5) Uani 1 1 d . . .
C30 C 0.1399(3) 0.31925(19) 0.37167(11) 0.0153(5) Uani 1 1 d . . .
N6 N -0.1315(3) 0.21173(16) 0.29364(9) 0.0168(5) Uani 1 1 d D . .
H106 H -0.055(3) 0.191(2) 0.2603(9) 0.039(9) Uiso 1 1 d D . .
N7 N 0.0525(3) 0.29561(16) 0.32720(9) 0.0159(5) Uani 1 1 d D . .
H107 H 0.067(4) 0.323(2) 0.2895(9) 0.053(10) Uiso 1 1 d D . .
N8 N 0.2042(3) 0.39973(17) 0.36309(10) 0.0199(5) Uani 1 1 d D . .
H108 H 0.279(3) 0.411(2) 0.3870(11) 0.044(9) Uiso 1 1 d D . .
H208 H 0.174(4) 0.4500(19) 0.3333(10) 0.046(9) Uiso 1 1 d D . .
N9 N -0.1968(3) 0.28559(17) 0.38939(10) 0.0204(5) Uani 1 1 d D . .
H109 H -0.302(3) 0.272(2) 0.3942(12) 0.043(9) Uiso 1 1 d D . .
H209 H -0.181(3) 0.3360(18) 0.4146(10) 0.036(8) Uiso 1 1 d D . .
N10 N 0.1610(3) 0.25671(17) 0.41959(10) 0.0171(5) Uani 1 1 d D . .
H110 H 0.200(3) 0.2817(19) 0.4517(9) 0.029(8) Uiso 1 1 d D . .
H210 H 0.143(3) 0.1928(15) 0.4189(12) 0.032(8) Uiso 1 1 d D . .
C31 C 0.4938(3) 0.8338(2) 0.46322(11) 0.0235(6) Uani 1 1 d . . .
H31A H 0.4128 0.9046 0.4567 0.035 Uiso 1 1 calc R . .
H31B H 0.6139 0.8391 0.4601 0.035 Uiso 1 1 calc R . .
H31C H 0.4621 0.8074 0.5036 0.035 Uiso 1 1 calc R . .
C32 C 0.4824(3) 0.75753(19) 0.41602(11) 0.0177(6) Uani 1 1 d . . .
C33 C 0.3366(3) 0.7205(2) 0.41741(12) 0.0219(6) Uani 1 1 d . . .
H33 H 0.2442 0.7427 0.4495 0.026 Uiso 1 1 calc R . .
C34 C 0.3212(3) 0.6526(2) 0.37389(12) 0.0238(6) Uani 1 1 d . . .
H34 H 0.2183 0.6301 0.3758 0.029 Uiso 1 1 calc R . .
C35 C 0.4548(3) 0.6176(2) 0.32772(12) 0.0250(6) Uani 1 1 d . . .
H35 H 0.4448 0.5708 0.2976 0.030 Uiso 1 1 calc R . .
C36 C 0.6039(3) 0.6510(2) 0.32553(11) 0.0226(6) Uani 1 1 d . . .
H36 H 0.6974 0.6265 0.2941 0.027 Uiso 1 1 calc R . .
C37 C 0.6171(3) 0.72028(19) 0.36926(11) 0.0169(6) Uani 1 1 d . . .
C38 C 0.8324(3) 0.80737(18) 0.32352(11) 0.0145(5) Uani 1 1 d . . .
C39 C 1.1026(3) 0.85758(18) 0.29263(11) 0.0133(5) Uani 1 1 d . . .
N11 N 0.7735(3) 0.75200(17) 0.36761(9) 0.0171(5) Uani 1 1 d D . .
H111 H 0.837(3) 0.731(2) 0.3981(9) 0.030(8) Uiso 1 1 d D . .
N12 N 0.9736(3) 0.84034(16) 0.33421(9) 0.0148(5) Uani 1 1 d D . .
H112 H 0.976(3) 0.8518(17) 0.3733(7) 0.010(6) Uiso 1 1 d D . .
N13 N 1.2010(3) 0.91176(17) 0.31075(10) 0.0170(5) Uani 1 1 d D . .
H113 H 1.294(3) 0.919(2) 0.2839(10) 0.030(8) Uiso 1 1 d D . .
H213 H 1.170(3) 0.9501(19) 0.3458(9) 0.034(8) Uiso 1 1 d D . .
N14 N 0.7600(3) 0.83480(17) 0.27382(9) 0.0167(5) Uani 1 1 d D . .
H114 H 0.662(3) 0.818(2) 0.2673(13) 0.052(10) Uiso 1 1 d D . .
H214 H 0.794(3) 0.8841(18) 0.2484(10) 0.034(8) Uiso 1 1 d D . .
N15 N 1.1337(3) 0.81910(17) 0.23768(9) 0.0159(5) Uani 1 1 d D . .
H115 H 1.073(3) 0.7799(17) 0.2233(10) 0.020(7) Uiso 1 1 d D . .
H215 H 1.224(3) 0.834(2) 0.2149(10) 0.030(8) Uiso 1 1 d D . .
O13 O 0.9167(2) 0.62555(14) 0.46256(8) 0.0211(4) Uani 1 1 d D . .
H13O H 0.884(4) 0.5663(17) 0.4619(13) 0.048(10) Uiso 1 1 d D . .
H23O H 1.015(3) 0.606(2) 0.4789(13) 0.053(10) Uiso 1 1 d D . .
O14 O 0.0504(3) 0.29210(15) 0.09143(8) 0.0248(4) Uani 1 1 d D . .
H14O H 0.062(3) 0.290(2) 0.1294(8) 0.029(8) Uiso 1 1 d D . .
H24O H 0.003(4) 0.3629(14) 0.0887(13) 0.048(10) Uiso 1 1 d D . .
O15 O 0.0265(3) 0.10013(16) 0.18605(9) 0.0279(5) Uani 1 1 d D . .
H15O H -0.046(3) 0.0635(19) 0.1863(12) 0.035(9) Uiso 1 1 d D . .
H25O H 0.112(4) 0.070(3) 0.1598(14) 0.093(15) Uiso 1 1 d D . .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.251(3) . ?
C1 C4 1.461(3) . ?
C1 C2 1.467(3) . ?
C2 O2 1.256(3) . ?
C2 C3 1.456(3) . ?
C3 O3 1.261(3) . ?
C3 C4 1.464(3) . ?
C4 O4 1.254(3) . ?
C5 O5 1.262(3) . ?
C5 C6 1.455(3) 2_666 ?
C5 C6 1.464(3) . ?
C6 O6 1.251(3) . ?
C6 C5 1.455(3) 2_666 ?
C7 O7 1.241(3) . ?
C7 C10 1.464(3) . ?
C7 C8 1.465(3) . ?
C8 O8 1.258(3) . ?
C8 C9 1.463(3) . ?
C9 O9 1.260(3) . ?
C9 C10 1.442(3) . ?
C10 O10 1.260(3) . ?
C11 O11 1.251(3) . ?
C11 C12 1.457(3) 2_556 ?
C11 C12 1.462(3) . ?
C12 O12 1.252(3) . ?
C12 C11 1.457(3) 2_556 ?
C13 C14 1.494(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.386(3) . ?
C14 C19 1.394(3) . ?
C15 C16 1.376(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 N1 1.429(3) . ?
C20 N4 1.304(3) . ?
C20 N1 1.317(3) . ?
C20 N2 1.372(3) . ?
C21 N5 1.304(3) . ?
C21 N3 1.319(3) . ?
C21 N2 1.373(3) . ?
N1 H101 0.885(16) . ?
N2 H102 0.898(16) . ?
N3 H103 0.891(16) . ?
N3 H203 0.910(16) . ?
N4 H104 0.901(16) . ?
N4 H204 0.926(17) . ?
N5 H105 0.904(16) . ?
N5 H205 0.889(17) . ?
C22 C23 1.484(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.381(3) . ?
C23 C24 1.395(3) . ?
C24 C25 1.376(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.370(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C28 N6 1.436(3) . ?
C29 N9 1.302(3) . ?
C29 N6 1.319(3) . ?
C29 N7 1.372(3) . ?
C30 N8 1.297(3) . ?
C30 N10 1.313(3) . ?
C30 N7 1.374(3) . ?
N6 H106 0.898(16) . ?
N7 H107 0.907(17) . ?
N8 H108 0.893(17) . ?
N8 H208 0.917(17) . ?
N9 H109 0.906(17) . ?
N9 H209 0.927(17) . ?
N10 H110 0.922(16) . ?
N10 H210 0.888(16) . ?
C31 C32 1.504(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.386(3) . ?
C32 C37 1.393(3) . ?
C33 C34 1.379(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.375(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.388(3) . ?
C36 H36 0.9500 . ?
C37 N11 1.428(3) . ?
C38 N14 1.301(3) . ?
C38 N11 1.317(3) . ?
C38 N12 1.373(3) . ?
C39 N15 1.307(3) . ?
C39 N13 1.309(3) . ?
C39 N12 1.363(3) . ?
N11 H111 0.883(16) . ?
N12 H112 0.892(15) . ?
N13 H113 0.920(16) . ?
N13 H213 0.911(16) . ?
N14 H114 0.905(17) . ?
N14 H214 0.920(16) . ?
N15 H115 0.892(16) . ?
N15 H215 0.893(16) . ?
O13 H13O 0.886(17) . ?
O13 H23O 0.873(17) . ?
O14 H14O 0.861(16) . ?
O14 H24O 0.893(17) . ?
O15 H15O 0.855(16) . ?
O15 H25O 0.855(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 134.1(2) . . ?
O1 C1 C2 135.9(2) . . ?
C4 C1 C2 89.94(18) . . ?
O2 C2 C3 134.6(2) . . ?
O2 C2 C1 135.5(2) . . ?
C3 C2 C1 89.90(18) . . ?
O3 C3 C2 134.4(2) . . ?
O3 C3 C4 135.4(2) . . ?
C2 C3 C4 90.25(18) . . ?
O4 C4 C1 133.0(2) . . ?
O4 C4 C3 137.1(2) . . ?
C1 C4 C3 89.87(18) . . ?
O5 C5 C6 134.7(2) . 2_666 ?
O5 C5 C6 134.9(2) . . ?
C6 C5 C6 90.40(19) 2_666 . ?
O6 C6 C5 134.5(2) . 2_666 ?
O6 C6 C5 135.9(2) . . ?
C5 C6 C5 89.6(2) 2_666 . ?
O7 C7 C10 135.0(2) . . ?
O7 C7 C8 135.9(2) . . ?
C10 C7 C8 89.14(19) . . ?
O8 C8 C9 135.4(2) . . ?
O8 C8 C7 134.6(2) . . ?
C9 C8 C7 89.95(19) . . ?
O9 C9 C10 133.8(2) . . ?
O9 C9 C8 136.1(2) . . ?
C10 C9 C8 90.07(19) . . ?
O10 C10 C9 134.7(2) . . ?
O10 C10 C7 134.4(2) . . ?
C9 C10 C7 90.83(19) . . ?
O11 C11 C12 134.7(2) . 2_556 ?
O11 C11 C12 135.1(2) . . ?
C12 C11 C12 90.3(2) 2_556 . ?
O12 C12 C11 135.5(2) . 2_556 ?
O12 C12 C11 134.8(2) . . ?
C11 C12 C11 89.7(2) 2_556 . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 116.8(2) . . ?
C15 C14 C13 120.9(2) . . ?
C19 C14 C13 122.3(2) . . ?
C16 C15 C14 122.2(2) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 119.7(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 121.7(2) . . ?
C18 C19 N1 120.4(2) . . ?
C14 C19 N1 117.7(2) . . ?
N4 C20 N1 123.7(2) . . ?
N4 C20 N2 121.3(2) . . ?
N1 C20 N2 114.7(2) . . ?
N5 C21 N3 123.7(2) . . ?
N5 C21 N2 121.2(2) . . ?
N3 C21 N2 115.1(2) . . ?
C20 N1 C19 125.4(2) . . ?
C20 N1 H101 116.3(15) . . ?
C19 N1 H101 117.7(15) . . ?
C20 N2 C21 127.5(2) . . ?
C20 N2 H102 115.9(15) . . ?
C21 N2 H102 116.3(15) . . ?
C21 N3 H103 117.3(17) . . ?
C21 N3 H203 121.5(16) . . ?
H103 N3 H203 120(2) . . ?
C20 N4 H104 122.8(17) . . ?
C20 N4 H204 120.8(17) . . ?
H104 N4 H204 116(2) . . ?
C21 N5 H105 118.4(16) . . ?
C21 N5 H205 117.1(19) . . ?
H105 N5 H205 120(2) . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 116.9(2) . . ?
C28 C23 C22 122.0(2) . . ?
C24 C23 C22 121.2(2) . . ?
C25 C24 C23 120.9(3) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C24 121.2(3) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C27 C26 C25 118.9(3) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C28 119.9(3) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C23 C28 C27 122.2(2) . . ?
C23 C28 N6 118.4(2) . . ?
C27 C28 N6 119.4(2) . . ?
N9 C29 N6 123.5(2) . . ?
N9 C29 N7 120.3(2) . . ?
N6 C29 N7 116.2(2) . . ?
N8 C30 N10 123.0(2) . . ?
N8 C30 N7 118.3(2) . . ?
N10 C30 N7 118.6(2) . . ?
C29 N6 C28 123.9(2) . . ?
C29 N6 H106 122.0(18) . . ?
C28 N6 H106 114.0(18) . . ?
C29 N7 C30 124.2(2) . . ?
C29 N7 H107 113.7(19) . . ?
C30 N7 H107 119.0(19) . . ?
C30 N8 H108 121.7(18) . . ?
C30 N8 H208 122.8(18) . . ?
H108 N8 H208 115(3) . . ?
C29 N9 H109 119.6(18) . . ?
C29 N9 H209 119.1(16) . . ?
H109 N9 H209 118(2) . . ?
C30 N10 H110 116.3(16) . . ?
C30 N10 H210 119.8(17) . . ?
H110 N10 H210 124(2) . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C37 116.9(2) . . ?
C33 C32 C31 121.2(2) . . ?
C37 C32 C31 121.9(2) . . ?
C34 C33 C32 122.3(2) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C35 C34 C33 119.9(2) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 119.4(3) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C35 C36 C37 120.1(2) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C36 C37 C32 121.3(2) . . ?
C36 C37 N11 119.7(2) . . ?
C32 C37 N11 118.9(2) . . ?
N14 C38 N11 123.8(2) . . ?
N14 C38 N12 120.6(2) . . ?
N11 C38 N12 115.5(2) . . ?
N15 C39 N13 120.4(2) . . ?
N15 C39 N12 122.7(2) . . ?
N13 C39 N12 116.9(2) . . ?
C38 N11 C37 125.0(2) . . ?
C38 N11 H111 117.7(17) . . ?
C37 N11 H111 117.3(17) . . ?
C39 N12 C38 127.6(2) . . ?
C39 N12 H112 119.1(14) . . ?
C38 N12 H112 113.4(14) . . ?
C39 N13 H113 117.3(16) . . ?
C39 N13 H213 121.9(17) . . ?
H113 N13 H213 120(2) . . ?
C38 N14 H114 121.7(19) . . ?
C38 N14 H214 119.0(16) . . ?
H114 N14 H214 118(2) . . ?
C39 N15 H115 124.2(16) . . ?
C39 N15 H215 114.7(17) . . ?
H115 N15 H215 121(2) . . ?
H13O O13 H23O 105(3) . . ?
H14O O14 H24O 97(2) . . ?
H15O O15 H25O 105(3) . . ?

_diffrn_measured_fraction_theta_max .996
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full .996
_refine_diff_density_max         .280
_refine_diff_density_min         -.304
_refine_diff_density_rms         .055
_database_code_depnum_ccdc_archive 'CCDC 1018224'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3c
#==============================================================================

# CHEMICAL DATA 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H15 N5, C9 H14 N5, C4 H O4, C4 O4'
_chemical_formula_sum            'C26 H30 N10 O8'
_chemical_formula_weight         610.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc

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

_cell_length_a                   11.7133(7)
_cell_length_b                   12.8357(7)
_cell_length_c                   19.3224(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3550(10)
_cell_angle_gamma                90.00
_cell_volume                     2905.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5765
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.60

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#==============================================================================

# EXPERIMENTAL DATA 

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Bruker APEXI CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        'no decay'
_diffrn_reflns_number            39601
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         28.39
_reflns_number_total             7265
_reflns_number_gt                6043
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

#==============================================================================

# REFINEMENT DATA 

_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)+(0.0379P)²+1.5690P] 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         7265
_refine_ls_number_parameters     488
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.69595(12) 0.83913(10) 0.36433(7) 0.0170(3) Uani 1 1 d . . .
C2 C 0.67139(12) 0.73113(11) 0.37817(7) 0.0178(3) Uani 1 1 d . . .
C3 C 0.62681(12) 0.76162(11) 0.44644(7) 0.0173(3) Uani 1 1 d . . .
C4 C 0.65308(12) 0.87290(10) 0.43085(7) 0.0169(3) Uani 1 1 d . . .
O1 O 0.74039(9) 0.88702(8) 0.31120(5) 0.0208(2) Uani 1 1 d D . .
H1 H 0.7347(19) 0.9569(12) 0.3168(11) 0.050(6) Uiso 1 1 d D . .
O2 O 0.68052(10) 0.64588(8) 0.34759(5) 0.0248(2) Uani 1 1 d . . .
O3 O 0.58459(9) 0.71372(8) 0.49566(5) 0.0213(2) Uani 1 1 d . . .
O4 O 0.64186(10) 0.95613(8) 0.46220(5) 0.0227(2) Uani 1 1 d . . .
C5 C 0.33646(12) 0.73734(10) 0.24661(7) 0.0156(3) Uani 1 1 d . . .
C6 C 0.30835(12) 0.62951(10) 0.23074(7) 0.0154(3) Uani 1 1 d . . .
C7 C 0.32123(12) 0.60083(11) 0.30330(7) 0.0179(3) Uani 1 1 d . . .
C8 C 0.35209(12) 0.70885(10) 0.31998(7) 0.0168(3) Uani 1 1 d . . .
O5 O 0.34404(9) 0.82028(7) 0.21271(5) 0.0187(2) Uani 1 1 d . . .
O6 O 0.28084(9) 0.58077(7) 0.17585(5) 0.0181(2) Uani 1 1 d . . .
O7 O 0.30908(10) 0.51948(8) 0.33788(5) 0.0241(2) Uani 1 1 d . . .
O8 O 0.37911(10) 0.75568(8) 0.37431(5) 0.0221(2) Uani 1 1 d . . .
N1 N 0.24053(11) 1.23359(10) 0.31403(7) 0.0199(3) Uani 1 1 d D . .
H10 H 0.2203(17) 1.2852(13) 0.2870(9) 0.036(5) Uiso 1 1 d D . .
N2 N 0.40884(10) 1.15151(9) 0.35661(6) 0.0183(2) Uani 1 1 d . . .
N3 N 0.35833(12) 1.02381(10) 0.27522(7) 0.0223(3) Uani 1 1 d D . .
H30 H 0.3479(16) 0.9570(12) 0.2636(9) 0.030(5) Uiso 1 1 d D . .
H30A H 0.3513(17) 1.0716(14) 0.2421(9) 0.035(5) Uiso 1 1 d D . .
N4 N 0.40945(12) 1.32125(10) 0.32115(7) 0.0223(3) Uani 1 1 d D . .
H40 H 0.4844(12) 1.3211(14) 0.3213(9) 0.026(5) Uiso 1 1 d D . .
H40A H 0.3694(16) 1.3805(13) 0.3159(10) 0.037(5) Uiso 1 1 d D . .
N5 N 0.39999(12) 0.98003(10) 0.38793(7) 0.0221(3) Uani 1 1 d D . .
H50 H 0.4058(17) 1.0004(15) 0.4315(8) 0.034(5) Uiso 1 1 d D . .
H50A H 0.3918(17) 0.9128(12) 0.3778(10) 0.041(6) Uiso 1 1 d D . .
C15 C 0.15757(12) 1.16170(11) 0.33760(8) 0.0209(3) Uani 1 1 d . . .
C14 C 0.16452(14) 1.12204(13) 0.40447(8) 0.0251(3) Uani 1 1 d . . .
H14C H 0.2238 1.1443 0.4348 0.030 Uiso 1 1 calc R . .
C13 C 0.08473(16) 1.04999(15) 0.42678(9) 0.0337(4) Uani 1 1 d . . .
H13 H 0.0904 1.0217 0.4721 0.040 Uiso 1 1 calc R . .
C12 C -0.00292(15) 1.01910(15) 0.38335(10) 0.0365(4) Uani 1 1 d . . .
H12 H -0.0573 0.9693 0.3985 0.044 Uiso 1 1 calc R . .
C11 C -0.01098(14) 1.06106(14) 0.31772(9) 0.0316(4) Uani 1 1 d . . .
H11 H -0.0722 1.0402 0.2883 0.038 Uiso 1 1 calc R . .
C10 C 0.06792(13) 1.13304(12) 0.29340(8) 0.0252(3) Uani 1 1 d . . .
C9 C 0.05625(15) 1.17834(15) 0.22194(9) 0.0344(4) Uani 1 1 d . . .
H9A H -0.0122 1.1499 0.1994 0.052 Uiso 1 1 calc R . .
H9B H 0.1237 1.1603 0.1947 0.052 Uiso 1 1 calc R . .
H9C H 0.0496 1.2543 0.2252 0.052 Uiso 1 1 calc R . .
C16 C 0.35371(12) 1.23190(10) 0.33022(7) 0.0170(3) Uani 1 1 d . . .
C17 C 0.38563(12) 1.05212(11) 0.33922(7) 0.0174(3) Uani 1 1 d . . .
N6 N 0.21306(10) 0.76971(9) 0.57653(6) 0.0176(2) Uani 1 1 d D . .
H60 H 0.2146(16) 0.8197(13) 0.6082(9) 0.030(5) Uiso 1 1 d D . .
N7 N 0.32733(11) 0.67086(9) 0.50059(6) 0.0166(2) Uani 1 1 d D . .
H70 H 0.3533(16) 0.6840(15) 0.4582(8) 0.036(5) Uiso 1 1 d D . .
N8 N 0.33669(11) 0.55237(9) 0.59203(6) 0.0179(2) Uani 1 1 d D . .
H80 H 0.3350(15) 0.4857(11) 0.6077(9) 0.024(4) Uiso 1 1 d D . .
H80A H 0.3297(15) 0.6041(12) 0.6221(8) 0.025(5) Uiso 1 1 d D . .
N9 N 0.38901(11) 0.82874(10) 0.54271(7) 0.0207(3) Uani 1 1 d D . .
H90 H 0.3766(16) 0.8900(12) 0.5623(9) 0.031(5) Uiso 1 1 d D . .
H90A H 0.4588(14) 0.8086(15) 0.5308(10) 0.038(5) Uiso 1 1 d D . .
N10 N 0.35656(11) 0.49777(9) 0.47903(6) 0.0182(2) Uani 1 1 d D . .
H100 H 0.3730(15) 0.4333(12) 0.4929(9) 0.027(5) Uiso 1 1 d D . .
H101 H 0.3471(17) 0.5121(15) 0.4336(8) 0.035(5) Uiso 1 1 d D . .
C24 C 0.11352(16) 0.70476(15) 0.57292(11) 0.0203(4) Uani 0.815(3) 1 d PD A 1
C23 C 0.08011(17) 0.65498(16) 0.63348(13) 0.0266(5) Uani 0.815(3) 1 d PD A 1
H23 H 0.1241 0.6629 0.6746 0.032 Uiso 0.815(3) 1 calc PR A 1
C22 C -0.01693(18) 0.59408(17) 0.63370(13) 0.0359(6) Uani 0.815(3) 1 d PD A 1
H22 H -0.0403 0.5602 0.6750 0.043 Uiso 0.815(3) 1 calc PR A 1
C21 C -0.0796(2) 0.5827(2) 0.57388(15) 0.0421(6) Uani 0.815(3) 1 d PD A 1
H21 H -0.1458 0.5400 0.5736 0.050 Uiso 0.815(3) 1 calc PR A 1
C20 C -0.0468(2) 0.63289(19) 0.51453(15) 0.0400(6) Uani 0.815(3) 1 d PD A 1
H20 H -0.0916 0.6245 0.4738 0.048 Uiso 0.815(3) 1 calc PR A 1
C19 C 0.05068(17) 0.69607(16) 0.51211(11) 0.0284(5) Uani 0.815(3) 1 d PD A 1
C18 C 0.0828(2) 0.7528(2) 0.44706(13) 0.0410(6) Uani 0.815(3) 1 d PD A 1
H18A H 0.1217 0.8180 0.4591 0.061 Uiso 0.815(3) 1 calc PR A 1
H18B H 0.0137 0.7684 0.4201 0.061 Uiso 0.815(3) 1 calc PR A 1
H18C H 0.1339 0.7090 0.4195 0.061 Uiso 0.815(3) 1 calc PR A 1
C24A C 0.1064(8) 0.7218(8) 0.5472(5) 0.0255(12) Uiso 0.185(3) 1 d PD A 2
C23A C 0.0410(7) 0.6604(6) 0.5908(4) 0.0255(12) Uiso 0.185(3) 1 d PD A 2
C22A C -0.0618(8) 0.6214(8) 0.5633(5) 0.0255(12) Uiso 0.185(3) 1 d PD A 2
H22A H -0.1104 0.5803 0.5915 0.031 Uiso 0.185(3) 1 calc PR A 2
C21A C -0.0927(8) 0.6419(7) 0.4960(4) 0.0255(12) Uiso 0.185(3) 1 d PD A 2
H21A H -0.1607 0.6119 0.4779 0.031 Uiso 0.185(3) 1 calc PR A 2
C20A C -0.0281(6) 0.7044(6) 0.4544(4) 0.0255(12) Uiso 0.185(3) 1 d PD A 2
H20A H -0.0519 0.7204 0.4085 0.031 Uiso 0.185(3) 1 calc PR A 2
C19A C 0.0734(7) 0.7438(7) 0.4813(5) 0.0255(12) Uiso 0.185(3) 1 d PD A 2
H19A H 0.1203 0.7866 0.4532 0.031 Uiso 0.185(3) 1 calc PR A 2
C18A C 0.0766(11) 0.6365(10) 0.6641(6) 0.037(3) Uiso 0.185(3) 1 d PD A 2
H18D H 0.1315 0.5789 0.6642 0.055 Uiso 0.185(3) 1 calc PR A 2
H18E H 0.0093 0.6167 0.6910 0.055 Uiso 0.185(3) 1 calc PR A 2
H18F H 0.1121 0.6983 0.6849 0.055 Uiso 0.185(3) 1 calc PR A 2
C25 C 0.30920(12) 0.75808(10) 0.54191(7) 0.0156(3) Uani 1 1 d . A .
C26 C 0.33964(11) 0.57169(10) 0.52506(7) 0.0153(3) Uani 1 1 d . A .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3074(17) . ?
C1 C2 1.4412(19) . ?
C1 C4 1.4492(19) . ?
C2 O2 1.2486(17) . ?
C2 C3 1.4746(19) . ?
C3 O3 1.2381(17) . ?
C3 C4 1.4921(19) . ?
C4 O4 1.2356(17) . ?
O1 H1 0.906(16) . ?
C5 O5 1.2534(16) . ?
C5 C6 1.4549(18) . ?
C5 C8 1.4743(19) . ?
C6 O6 1.2712(16) . ?
C6 C7 1.4564(19) . ?
C7 O7 1.2483(17) . ?
C7 C8 1.4682(19) . ?
C8 O8 1.2487(17) . ?
N1 C16 1.3604(19) . ?
N1 C15 1.4172(19) . ?
N1 H10 0.874(15) . ?
N2 C16 1.3183(18) . ?
N2 C17 1.3465(18) . ?
N3 C17 1.3260(19) . ?
N3 H30 0.895(14) . ?
N3 H30A 0.890(15) . ?
N4 C16 1.3318(18) . ?
N4 H40 0.878(14) . ?
N4 H40A 0.899(15) . ?
N5 C17 1.3298(18) . ?
N5 H50 0.883(15) . ?
N5 H50A 0.890(15) . ?
C15 C14 1.391(2) . ?
C15 C10 1.399(2) . ?
C14 C13 1.386(2) . ?
C14 H14C 0.9500 . ?
C13 C12 1.380(3) . ?
C13 H13 0.9500 . ?
C12 C11 1.381(3) . ?
C12 H12 0.9500 . ?
C11 C10 1.391(2) . ?
C11 H11 0.9500 . ?
C10 C9 1.503(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N6 C25 1.3219(18) . ?
N6 C24 1.435(2) . ?
N6 C24A 1.500(8) . ?
N6 H60 0.887(14) . ?
N7 C26 1.3652(17) . ?
N7 C25 1.3922(17) . ?
N7 H70 0.891(15) . ?
N8 C26 1.3182(18) . ?
N8 H80 0.907(14) . ?
N8 H80A 0.887(14) . ?
N9 C25 1.3025(19) . ?
N9 H90 0.885(14) . ?
N9 H90A 0.889(15) . ?
N10 C26 1.3163(18) . ?
N10 H100 0.890(14) . ?
N10 H101 0.902(15) . ?
C24 C19 1.387(3) . ?
C24 C23 1.392(3) . ?
C23 C22 1.379(3) . ?
C23 H23 0.9500 . ?
C22 C21 1.373(4) . ?
C22 H22 0.9500 . ?
C21 C20 1.372(4) . ?
C21 H21 0.9500 . ?
C20 C19 1.401(3) . ?
C20 H20 0.9500 . ?
C19 C18 1.502(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C24A C19A 1.358(10) . ?
C24A C23A 1.389(9) . ?
C23A C22A 1.406(10) . ?
C23A C18A 1.506(12) . ?
C22A C21A 1.372(10) . ?
C22A H22A 0.9500 . ?
C21A C20A 1.367(9) . ?
C21A H21A 0.9500 . ?
C20A C19A 1.390(9) . ?
C20A H20A 0.9500 . ?
C19A H19A 0.9500 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 132.76(13) . . ?
O1 C1 C4 134.23(13) . . ?
C2 C1 C4 93.00(11) . . ?
O2 C2 C1 137.51(13) . . ?
O2 C2 C3 133.46(13) . . ?
C1 C2 C3 89.02(11) . . ?
O3 C3 C2 134.47(13) . . ?
O3 C3 C4 135.59(13) . . ?
C2 C3 C4 89.94(11) . . ?
O4 C4 C1 137.05(13) . . ?
O4 C4 C3 134.91(13) . . ?
C1 C4 C3 88.04(11) . . ?
C1 O1 H1 110.0(14) . . ?
O5 C5 C6 135.60(13) . . ?
O5 C5 C8 134.78(13) . . ?
C6 C5 C8 89.62(11) . . ?
O6 C6 C5 134.42(12) . . ?
O6 C6 C7 134.67(12) . . ?
C5 C6 C7 90.89(11) . . ?
O7 C7 C6 135.67(13) . . ?
O7 C7 C8 134.52(13) . . ?
C6 C7 C8 89.80(11) . . ?
O8 C8 C7 134.42(13) . . ?
O8 C8 C5 135.91(13) . . ?
C7 C8 C5 89.67(11) . . ?
C16 N1 C15 125.79(12) . . ?
C16 N1 H10 114.1(13) . . ?
C15 N1 H10 120.1(13) . . ?
C16 N2 C17 123.19(13) . . ?
C17 N3 H30 121.9(12) . . ?
C17 N3 H30A 120.2(13) . . ?
H30 N3 H30A 117.9(18) . . ?
C16 N4 H40 119.3(12) . . ?
C16 N4 H40A 119.2(13) . . ?
H40 N4 H40A 121.5(17) . . ?
C17 N5 H50 118.5(13) . . ?
C17 N5 H50A 120.3(13) . . ?
H50 N5 H50A 120.3(18) . . ?
C14 C15 C10 120.70(14) . . ?
C14 C15 N1 120.04(14) . . ?
C10 C15 N1 119.25(14) . . ?
C13 C14 C15 119.85(15) . . ?
C13 C14 H14C 120.1 . . ?
C15 C14 H14C 120.1 . . ?
C12 C13 C14 120.21(16) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C12 C11 119.53(16) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C11 C10 121.86(16) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C10 C15 117.80(15) . . ?
C11 C10 C9 120.69(15) . . ?
C15 C10 C9 121.51(14) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C16 N4 119.05(13) . . ?
N2 C16 N1 125.15(13) . . ?
N4 C16 N1 115.71(13) . . ?
N3 C17 N5 119.87(13) . . ?
N3 C17 N2 122.65(13) . . ?
N5 C17 N2 117.26(13) . . ?
C25 N6 C24 127.19(13) . . ?
C25 N6 C24A 118.2(4) . . ?
C24 N6 C24A 21.4(3) . . ?
C25 N6 H60 114.7(12) . . ?
C24 N6 H60 117.8(12) . . ?
C24A N6 H60 124.8(13) . . ?
C26 N7 C25 124.57(12) . . ?
C26 N7 H70 117.3(13) . . ?
C25 N7 H70 115.4(13) . . ?
C26 N8 H80 120.3(11) . . ?
C26 N8 H80A 120.4(12) . . ?
H80 N8 H80A 119.0(16) . . ?
C25 N9 H90 120.3(12) . . ?
C25 N9 H90A 117.1(13) . . ?
H90 N9 H90A 121.5(18) . . ?
C26 N10 H100 120.0(12) . . ?
C26 N10 H101 119.5(13) . . ?
H100 N10 H101 120.5(17) . . ?
C19 C24 C23 121.66(18) . . ?
C19 C24 N6 120.98(18) . . ?
C23 C24 N6 117.30(17) . . ?
C22 C23 C24 119.9(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C21 C22 C23 119.6(2) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C20 C19 122.1(2) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C24 C19 C20 116.5(2) . . ?
C24 C19 C18 122.38(19) . . ?
C20 C19 C18 121.1(2) . . ?
C19A C24A C23A 122.2(7) . . ?
C19A C24A N6 120.1(7) . . ?
C23A C24A N6 117.6(6) . . ?
C24A C23A C22A 116.6(7) . . ?
C24A C23A C18A 122.5(8) . . ?
C22A C23A C18A 121.0(8) . . ?
C21A C22A C23A 120.6(7) . . ?
C21A C22A H22A 119.7 . . ?
C23A C22A H22A 119.7 . . ?
C20A C21A C22A 121.8(8) . . ?
C20A C21A H21A 119.1 . . ?
C22A C21A H21A 119.1 . . ?
C21A C20A C19A 117.9(7) . . ?
C21A C20A H20A 121.0 . . ?
C19A C20A H20A 121.0 . . ?
C24A C19A C20A 120.9(7) . . ?
C24A C19A H19A 119.6 . . ?
C20A C19A H19A 119.6 . . ?
C23A C18A H18D 109.5 . . ?
C23A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C23A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N9 C25 N6 121.94(13) . . ?
N9 C25 N7 117.05(13) . . ?
N6 C25 N7 120.96(13) . . ?
N10 C26 N8 122.18(13) . . ?
N10 C26 N7 117.01(12) . . ?
N8 C26 N7 120.80(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -0.8(3) . . . . ?
C4 C1 C2 O2 179.20(19) . . . . ?
O1 C1 C2 C3 179.99(16) . . . . ?
C4 C1 C2 C3 0.01(11) . . . . ?
O2 C2 C3 O3 0.3(3) . . . . ?
C1 C2 C3 O3 179.59(17) . . . . ?
O2 C2 C3 C4 -179.25(17) . . . . ?
C1 C2 C3 C4 -0.01(11) . . . . ?
O1 C1 C4 O4 0.1(3) . . . . ?
C2 C1 C4 O4 -179.88(18) . . . . ?
O1 C1 C4 C3 -179.99(17) . . . . ?
C2 C1 C4 C3 -0.01(11) . . . . ?
O3 C3 C4 O4 0.3(3) . . . . ?
C2 C3 C4 O4 179.88(17) . . . . ?
O3 C3 C4 C1 -179.58(18) . . . . ?
C2 C3 C4 C1 0.01(11) . . . . ?
O5 C5 C6 O6 -0.2(3) . . . . ?
C8 C5 C6 O6 179.56(16) . . . . ?
O5 C5 C6 C7 -178.65(17) . . . . ?
C8 C5 C6 C7 1.10(11) . . . . ?
O6 C6 C7 O7 -0.9(3) . . . . ?
C5 C6 C7 O7 177.55(18) . . . . ?
O6 C6 C7 C8 -179.56(16) . . . . ?
C5 C6 C7 C8 -1.10(11) . . . . ?
O7 C7 C8 O8 1.9(3) . . . . ?
C6 C7 C8 O8 -179.45(17) . . . . ?
O7 C7 C8 C5 -177.59(18) . . . . ?
C6 C7 C8 C5 1.09(11) . . . . ?
O5 C5 C8 O8 -0.8(3) . . . . ?
C6 C5 C8 O8 179.46(18) . . . . ?
O5 C5 C8 C7 178.66(17) . . . . ?
C6 C5 C8 C7 -1.09(11) . . . . ?
C16 N1 C15 C14 36.6(2) . . . . ?
C16 N1 C15 C10 -144.66(15) . . . . ?
C10 C15 C14 C13 2.8(2) . . . . ?
N1 C15 C14 C13 -178.54(15) . . . . ?
C15 C14 C13 C12 -1.3(3) . . . . ?
C14 C13 C12 C11 -0.5(3) . . . . ?
C13 C12 C11 C10 0.9(3) . . . . ?
C12 C11 C10 C15 0.5(3) . . . . ?
C12 C11 C10 C9 -179.31(17) . . . . ?
C14 C15 C10 C11 -2.3(2) . . . . ?
N1 C15 C10 C11 178.98(14) . . . . ?
C14 C15 C10 C9 177.50(15) . . . . ?
N1 C15 C10 C9 -1.2(2) . . . . ?
C17 N2 C16 N4 -147.29(14) . . . . ?
C17 N2 C16 N1 36.2(2) . . . . ?
C15 N1 C16 N2 16.6(2) . . . . ?
C15 N1 C16 N4 -160.03(14) . . . . ?
C16 N2 C17 N3 37.9(2) . . . . ?
C16 N2 C17 N5 -147.48(14) . . . . ?
C25 N6 C24 C19 -64.0(2) . . . . ?
C24A N6 C24 C19 7.9(12) . . . . ?
C25 N6 C24 C23 118.83(19) . . . . ?
C24A N6 C24 C23 -169.3(14) . . . . ?
C19 C24 C23 C22 0.8(3) . . . . ?
N6 C24 C23 C22 178.02(17) . . . . ?
C24 C23 C22 C21 0.3(3) . . . . ?
C23 C22 C21 C20 -1.0(3) . . . . ?
C22 C21 C20 C19 0.5(4) . . . . ?
C23 C24 C19 C20 -1.3(3) . . . . ?
N6 C24 C19 C20 -178.33(18) . . . . ?
C23 C24 C19 C18 177.4(2) . . . . ?
N6 C24 C19 C18 0.4(3) . . . . ?
C21 C20 C19 C24 0.6(3) . . . . ?
C21 C20 C19 C18 -178.1(2) . . . . ?
C25 N6 C24A C19A -53.9(11) . . . . ?
C24 N6 C24A C19A -175(2) . . . . ?
C25 N6 C24A C23A 129.8(8) . . . . ?
C24 N6 C24A C23A 9.0(6) . . . . ?
C19A C24A C23A C22A 0.2(15) . . . . ?
N6 C24A C23A C22A 176.5(8) . . . . ?
C19A C24A C23A C18A -179.5(10) . . . . ?
N6 C24A C23A C18A -3.2(15) . . . . ?
C24A C23A C22A C21A 1.5(15) . . . . ?
C18A C23A C22A C21A -178.8(10) . . . . ?
C23A C22A C21A C20A -3.0(15) . . . . ?
C22A C21A C20A C19A 2.6(14) . . . . ?
C23A C24A C19A C20A -0.5(16) . . . . ?
N6 C24A C19A C20A -176.7(8) . . . . ?
C21A C20A C19A C24A -0.9(14) . . . . ?
C24 N6 C25 N9 171.40(15) . . . . ?
C24A N6 C25 N9 148.2(4) . . . . ?
C24 N6 C25 N7 -6.0(2) . . . . ?
C24A N6 C25 N7 -29.2(5) . . . . ?
C26 N7 C25 N9 115.25(16) . . . . ?
C26 N7 C25 N6 -67.22(19) . . . . ?
C25 N7 C26 N10 -179.84(13) . . . . ?
C25 N7 C26 N8 -1.1(2) . . . . ?

_diffrn_measured_fraction_theta_max .998
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full .998
_refine_diff_density_max         .398
_refine_diff_density_min         -.289
_refine_diff_density_rms         .055
_database_code_depnum_ccdc_archive 'CCDC 1018225'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3d
#==============================================================================
# CHEMICAL DATA 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N5, 0.5(C4 O4)'
_chemical_formula_sum            'C11 H14 N5 O2'
_chemical_formula_weight         248.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn

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                   9.406(3)
_cell_length_b                   11.576(3)
_cell_length_c                   11.779(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.623(4)
_cell_angle_gamma                90.00
_cell_volume                     1222.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5511
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.31

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        'no decay'
_diffrn_reflns_number            14215
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         26.38
_reflns_number_total             2498
_reflns_number_gt                2075
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

#==============================================================================

# REFINEMENT DATA

_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)+(0.0620P)²+0.0254P] 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         2498
_refine_ls_number_parameters     192
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.09172(12) 0.45752(10) 0.05346(10) 0.0181(3) Uani 1 1 d . . .
C2 C 0.04085(12) 0.57691(9) 0.04214(10) 0.0179(3) Uani 1 1 d . . .
O1 O 0.20480(8) 0.40620(7) 0.11900(7) 0.0229(2) Uani 1 1 d . . .
O2 O 0.09107(9) 0.66953(7) 0.09373(7) 0.0216(2) Uani 1 1 d . . .
N1 N -0.18463(10) 0.95262(8) 0.12192(9) 0.0213(2) Uani 1 1 d . . .
N2 N 0.06160(11) 1.00897(8) 0.21005(8) 0.0193(2) Uani 1 1 d D . .
H20 H 0.1458(15) 0.9903(13) 0.2638(13) 0.037(4) Uiso 1 1 d D . .
N3 N 0.18714(11) 1.16681(9) 0.17356(9) 0.0203(2) Uani 1 1 d D . .
H30 H 0.1849(16) 1.2372(12) 0.1422(13) 0.039(4) Uiso 1 1 d D . .
H31 H 0.2574(15) 1.1574(12) 0.2453(12) 0.032(4) Uiso 1 1 d D . .
N4 N -0.05512(11) 1.13367(9) 0.05629(9) 0.0229(2) Uani 1 1 d D . .
H40 H -0.0551(15) 1.1987(11) 0.0139(12) 0.030(4) Uiso 1 1 d D . .
H41 H -0.1381(14) 1.0861(12) 0.0426(13) 0.035(4) Uiso 1 1 d D . .
N5 N -0.02976(13) 0.85908(10) 0.29195(10) 0.0287(3) Uani 1 1 d D . .
H50 H 0.0592(15) 0.8521(13) 0.3427(12) 0.036(4) Uiso 1 1 d D . .
H51 H -0.0965(16) 0.8076(12) 0.2886(13) 0.036(4) Uiso 1 1 d D . .
C3 C -0.43530(16) 1.04782(13) 0.17773(13) 0.0352(3) Uani 1 1 d . . .
H3A H -0.5353 1.0670 0.1813 0.053 Uiso 1 1 calc R . .
H3B H -0.4104 1.0976 0.1192 0.053 Uiso 1 1 calc R . .
H3C H -0.3625 1.0598 0.2563 0.053 Uiso 1 1 calc R . .
C4 C -0.43171(14) 0.92375(11) 0.14170(11) 0.0256(3) Uani 1 1 d . . .
C5 C -0.55225(14) 0.85099(13) 0.13001(11) 0.0324(3) Uani 1 1 d . . .
H5 H -0.6394 0.8807 0.1444 0.039 Uiso 1 1 calc R . .
C6 C -0.54924(15) 0.73640(13) 0.09809(11) 0.0346(3) Uani 1 1 d . . .
H6 H -0.6342 0.6888 0.0891 0.042 Uiso 1 1 calc R . .
C7 C -0.42262(15) 0.69139(12) 0.07929(11) 0.0304(3) Uani 1 1 d . . .
H7 H -0.4188 0.6121 0.0596 0.036 Uiso 1 1 calc R . .
C8 C -0.30106(14) 0.76230(11) 0.08919(11) 0.0242(3) Uani 1 1 d . . .
H8 H -0.2142 0.7316 0.0752 0.029 Uiso 1 1 calc R . .
C9 C -0.30495(12) 0.87821(11) 0.11939(10) 0.0206(3) Uani 1 1 d . . .
C10 C -0.06052(12) 0.93777(10) 0.20305(10) 0.0190(3) Uani 1 1 d . . .
C11 C 0.06260(13) 1.10548(9) 0.14486(10) 0.0180(3) Uani 1 1 d . . .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2582(13) . ?
C1 C2 1.4553(16) . ?
C1 C2 1.4600(15) 3_565 ?
C2 O2 1.2523(14) . ?
C2 C1 1.4600(15) 3_565 ?
N1 C10 1.2767(15) . ?
N1 C9 1.4154(15) . ?
N2 C11 1.3574(15) . ?
N2 C10 1.3958(15) . ?
N2 H20 0.879(13) . ?
N3 C11 1.3231(15) . ?
N3 H30 0.892(13) . ?
N3 H31 0.908(13) . ?
N4 C11 1.3120(15) . ?
N4 H40 0.904(12) . ?
N4 H41 0.929(12) . ?
N5 C10 1.3515(16) . ?
N5 H50 0.872(12) . ?
N5 H51 0.858(13) . ?
C3 C4 1.5010(19) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.3854(18) . ?
C4 C9 1.3995(17) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3835(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3914(18) . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 134.27(11) . . ?
O1 C1 C2 135.26(11) . 3_565 ?
C2 C1 C2 90.47(9) . 3_565 ?
O2 C2 C1 134.69(11) . . ?
O2 C2 C1 135.78(10) . 3_565 ?
C1 C2 C1 89.53(9) . 3_565 ?
C10 N1 C9 118.55(10) . . ?
C11 N2 C10 126.81(10) . . ?
C11 N2 H20 116.8(10) . . ?
C10 N2 H20 116.3(10) . . ?
C11 N3 H30 118.4(10) . . ?
C11 N3 H31 120.8(9) . . ?
H30 N3 H31 114.5(13) . . ?
C11 N4 H40 120.3(9) . . ?
C11 N4 H41 117.0(9) . . ?
H40 N4 H41 122.6(13) . . ?
C10 N5 H50 121.9(10) . . ?
C10 N5 H51 116.8(10) . . ?
H50 N5 H51 120.3(14) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 118.07(12) . . ?
C5 C4 C3 121.47(12) . . ?
C9 C4 C3 120.46(12) . . ?
C6 C5 C4 121.82(12) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C7 C6 C5 119.79(12) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 119.64(13) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.58(12) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 120.07(11) . . ?
C8 C9 N1 120.63(10) . . ?
C4 C9 N1 119.21(11) . . ?
N1 C10 N5 127.12(11) . . ?
N1 C10 N2 120.95(10) . . ?
N5 C10 N2 111.89(10) . . ?
N4 C11 N3 122.58(11) . . ?
N4 C11 N2 120.38(11) . . ?
N3 C11 N2 117.02(10) . . ?

_diffrn_measured_fraction_theta_max .997
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full .997
_refine_diff_density_max         .287
_refine_diff_density_min         -.184
_refine_diff_density_rms         .045
_database_code_depnum_ccdc_archive 'CCDC 1018226'
