# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_996724

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N6 O2, Cl'
_chemical_formula_sum            'C5 H9 Cl N6 O2'
_chemical_formula_weight         220.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   5.8923(5)
_cell_length_b                   11.4413(9)
_cell_length_c                   7.6951(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.239(3)
_cell_angle_gamma                90.00
_cell_volume                     480.18(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1804
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      24.72

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9066
_exptl_absorpt_correction_T_max  0.9236
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2670
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0739
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1648
_reflns_number_gt                1295
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'APEX2 (Bruker, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.1660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(12)
_refine_ls_number_reflns         1648
_refine_ls_number_parameters     128
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1909(8) 0.3967(4) 0.4897(6) 0.0258(11) Uani 1 1 d . . .
C2 C -0.2043(9) 0.4756(4) 0.3449(6) 0.0252(11) Uani 1 1 d . . .
C3 C -0.0511(10) 0.2880(4) 0.5612(7) 0.0313(12) Uani 1 1 d . . .
H3A H -0.0872 0.2587 0.6677 0.047 Uiso 1 1 calc R . .
H3B H 0.1248 0.3042 0.6022 0.047 Uiso 1 1 calc R . .
H3C H -0.0983 0.2291 0.4613 0.047 Uiso 1 1 calc R . .
C4 C -0.0793(8) 0.4712(4) 0.2156(6) 0.0272(11) Uani 1 1 d . . .
H4 H -0.0986 0.5329 0.1284 0.033 Uiso 1 1 calc R . .
C5 C 0.3210(8) 0.2993(4) 0.0931(6) 0.0217(11) Uani 1 1 d . . .
Cl1 Cl 0.8115(2) 0.08361(8) 0.16710(17) 0.0308(3) Uani 1 1 d . . .
N1 N -0.3382(8) 0.4378(4) 0.5671(6) 0.0326(10) Uani 1 1 d . . .
N2 N -0.3539(7) 0.5633(4) 0.3337(6) 0.0347(11) Uani 1 1 d . . .
N3 N 0.0573(7) 0.3838(3) 0.2195(5) 0.0226(9) Uani 1 1 d . . .
N4 N 0.1693(7) 0.3863(3) 0.0931(5) 0.0262(9) Uani 1 1 d . . .
H4A H 0.1420 0.4443 0.0128 0.031 Uiso 1 1 calc R . .
N5 N 0.3416(7) 0.2061(3) 0.1995(6) 0.0331(11) Uani 1 1 d . . .
H5A H 0.4435 0.1496 0.2005 0.040 Uiso 1 1 calc R . .
H5B H 0.2535 0.2005 0.2695 0.040 Uiso 1 1 calc R . .
N6 N 0.4507(7) 0.3099(3) -0.0128(6) 0.0282(11) Uani 1 1 d . . .
H6A H 0.5535 0.2542 -0.0136 0.034 Uiso 1 1 calc R . .
H6B H 0.4347 0.3725 -0.0827 0.034 Uiso 1 1 calc R . .
O1 O -0.4477(6) 0.5458(3) 0.4693(5) 0.0400(10) Uani 1 1 d . . .
O2 O -0.3952(8) 0.4101(4) 0.7006(6) 0.0529(11) Uani 1 1 d . . .


_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 N1 1.312(6) . ?
C1 C2 1.413(7) . ?
C1 C3 1.478(7) . ?
C2 N2 1.317(6) . ?
C2 C4 1.445(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N3 1.277(6) . ?
C4 H4 0.9500 . ?
C5 N6 1.317(6) . ?
C5 N5 1.322(6) . ?
C5 N4 1.337(6) . ?
N1 O2 1.237(5) . ?
N1 O1 1.464(5) . ?
N2 O1 1.368(5) . ?
N3 N4 1.367(5) . ?
N4 H4A 0.8800 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 106.3(4) . . ?
N1 C1 C3 120.2(4) . . ?
C2 C1 C3 133.5(4) . . ?
N2 C2 C1 112.0(4) . . ?
N2 C2 C4 119.0(4) . . ?
C1 C2 C4 129.0(4) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C4 C2 119.4(4) . . ?
N3 C4 H4 120.3 . . ?
C2 C4 H4 120.3 . . ?
N6 C5 N5 121.2(4) . . ?
N6 C5 N4 118.4(4) . . ?
N5 C5 N4 120.3(4) . . ?
O2 N1 C1 136.0(5) . . ?
O2 N1 O1 115.9(4) . . ?
C1 N1 O1 107.9(4) . . ?
C2 N2 O1 107.0(4) . . ?
C4 N3 N4 115.9(4) . . ?
C5 N4 N3 119.2(4) . . ?
C5 N4 H4A 120.4 . . ?
N3 N4 H4A 120.4 . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C5 N6 H6A 120.0 . . ?
C5 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
N2 O1 N1 106.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 996724'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N6 O2, C N5 O2'
_chemical_formula_sum            'C6 H9 N11 O4'
_chemical_formula_weight         299.24

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   10.9990(8)
_cell_length_b                   6.3838(4)
_cell_length_c                   18.1184(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.323(2)
_cell_angle_gamma                90.00
_cell_volume                     1232.65(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3048
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      25.69

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7739
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         26.02
_reflns_number_total             2380
_reflns_number_gt                1846
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0500P)²+0.3334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2380
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37027(15) 0.6375(3) 0.16162(9) 0.0209(4) Uani 1 1 d . . .
C2 C 0.93643(16) 1.0979(3) 0.10740(10) 0.0252(4) Uani 1 1 d . . .
C3 C 0.86316(15) 1.0199(3) 0.03733(9) 0.0216(4) Uani 1 1 d . . .
C4 C 0.9774(2) 1.0040(3) 0.18419(11) 0.0420(5) Uani 1 1 d . . .
H4A H 1.0561 1.0696 0.2119 0.063 Uiso 1 1 calc R . .
H4B H 0.9905 0.8532 0.1795 0.063 Uiso 1 1 calc R . .
H4C H 0.9128 1.0270 0.2121 0.063 Uiso 1 1 calc R . .
C5 C 0.79171(15) 0.8259(3) 0.02166(9) 0.0230(4) Uani 1 1 d . . .
H5 H 0.7647 0.7743 -0.0289 0.028 Uiso 1 1 calc R . .
C6 C 0.65921(15) 0.4390(2) 0.11105(9) 0.0201(4) Uani 1 1 d . . .
N1 N 0.40771(14) 0.8191(2) 0.19452(8) 0.0260(3) Uani 1 1 d . . .
N2 N 0.45050(14) 0.9221(2) 0.14146(8) 0.0277(3) Uani 1 1 d . . .
N3 N 0.43739(13) 0.8028(2) 0.08057(8) 0.0262(3) Uani 1 1 d . . .
N4 N 0.38634(13) 0.6185(2) 0.09211(7) 0.0241(3) Uani 1 1 d . . .
N5 N 0.31790(14) 0.4723(2) 0.19880(8) 0.0261(3) Uani 1 1 d . . .
N6 N 0.97551(14) 1.2843(2) 0.09252(9) 0.0301(4) Uani 1 1 d . . .
N7 N 0.86101(14) 1.1493(2) -0.01923(8) 0.0281(3) Uani 1 1 d . . .
N8 N 0.76590(13) 0.7262(2) 0.07695(8) 0.0214(3) Uani 1 1 d . . .
N9 N 0.69776(13) 0.5459(2) 0.05682(8) 0.0232(3) Uani 1 1 d . . .
H9 H 0.6796 0.5009 0.0094 0.028 Uiso 1 1 calc R . .
N10 N 0.59920(13) 0.2608(2) 0.09095(8) 0.0259(3) Uani 1 1 d . . .
H10A H 0.5733 0.1860 0.1249 0.031 Uiso 1 1 calc R . .
H10B H 0.5851 0.2167 0.0436 0.031 Uiso 1 1 calc R . .
N11 N 0.68324(14) 0.5134(2) 0.18084(8) 0.0259(3) Uani 1 1 d . . .
H11A H 0.6590 0.4437 0.2166 0.031 Uiso 1 1 calc R . .
H11B H 0.7235 0.6330 0.1918 0.031 Uiso 1 1 calc R . .
O1 O 0.29073(12) 0.5147(2) 0.25858(7) 0.0340(3) Uani 1 1 d . . .
O2 O 0.30553(14) 0.2992(2) 0.16904(8) 0.0404(4) Uani 1 1 d . . .
O3 O 0.92966(12) 1.32133(19) 0.01094(7) 0.0337(3) Uani 1 1 d . . .
O4 O 1.03841(14) 1.4251(2) 0.13082(8) 0.0485(4) Uani 1 1 d . . .


_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 N4 1.320(2) . ?
C1 N1 1.322(2) . ?
C1 N5 1.445(2) . ?
C2 N6 1.315(2) . ?
C2 C3 1.415(2) . ?
C2 C4 1.479(3) . ?
C3 N7 1.312(2) . ?
C3 C5 1.456(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N8 1.277(2) . ?
C5 H5 0.9500 . ?
C6 N11 1.315(2) . ?
C6 N10 1.321(2) . ?
C6 N9 1.348(2) . ?
N1 N2 1.3423(19) . ?
N2 N3 1.3186(19) . ?
N3 N4 1.343(2) . ?
N5 O2 1.2225(19) . ?
N5 O1 1.2232(18) . ?
N6 O4 1.2372(19) . ?
N6 O3 1.4583(19) . ?
N7 O3 1.3677(18) . ?
N8 N9 1.3731(18) . ?
N9 H9 0.8800 . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 114.24(14) . . ?
N4 C1 N5 122.71(15) . . ?
N1 C1 N5 123.05(13) . . ?
N6 C2 C3 106.07(15) . . ?
N6 C2 C4 121.35(16) . . ?
C3 C2 C4 132.43(17) . . ?
N7 C3 C2 112.04(15) . . ?
N7 C3 C5 118.59(15) . . ?
C2 C3 C5 129.35(15) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N8 C5 C3 119.00(15) . . ?
N8 C5 H5 120.5 . . ?
C3 C5 H5 120.5 . . ?
N11 C6 N10 122.98(15) . . ?
N11 C6 N9 119.57(15) . . ?
N10 C6 N9 117.44(14) . . ?
C1 N1 N2 103.41(13) . . ?
N3 N2 N1 109.35(14) . . ?
N2 N3 N4 109.83(13) . . ?
C1 N4 N3 103.17(13) . . ?
O2 N5 O1 124.45(15) . . ?
O2 N5 C1 117.89(13) . . ?
O1 N5 C1 117.64(14) . . ?
O4 N6 C2 135.08(16) . . ?
O4 N6 O3 117.11(14) . . ?
C2 N6 O3 107.82(13) . . ?
C3 N7 O3 106.98(13) . . ?
C5 N8 N9 114.98(14) . . ?
C6 N9 N8 118.71(13) . . ?
C6 N9 H9 120.6 . . ?
N8 N9 H9 120.6 . . ?
C6 N10 H10A 120.0 . . ?
C6 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C6 N11 H11A 120.0 . . ?
C6 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
N7 O3 N6 107.04(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N6 C2 C3 N7 2.4(2) . . . . ?
C4 C2 C3 N7 -172.98(19) . . . . ?
N6 C2 C3 C5 -176.24(16) . . . . ?
C4 C2 C3 C5 8.4(3) . . . . ?
N7 C3 C5 N8 -161.97(16) . . . . ?
C2 C3 C5 N8 16.6(3) . . . . ?
N4 C1 N1 N2 0.05(19) . . . . ?
N5 C1 N1 N2 179.18(15) . . . . ?
C1 N1 N2 N3 0.15(18) . . . . ?
N1 N2 N3 N4 -0.30(18) . . . . ?
N1 C1 N4 N3 -0.22(18) . . . . ?
N5 C1 N4 N3 -179.36(14) . . . . ?
N2 N3 N4 C1 0.31(17) . . . . ?
N4 C1 N5 O2 11.0(2) . . . . ?
N1 C1 N5 O2 -168.10(16) . . . . ?
N4 C1 N5 O1 -170.13(15) . . . . ?
N1 C1 N5 O1 10.8(2) . . . . ?
C3 C2 N6 O4 177.70(19) . . . . ?
C4 C2 N6 O4 -6.3(3) . . . . ?
C3 C2 N6 O3 -2.04(18) . . . . ?
C4 C2 N6 O3 173.97(16) . . . . ?
C2 C3 N7 O3 -1.65(19) . . . . ?
C5 C3 N7 O3 177.15(13) . . . . ?
C3 C5 N8 N9 179.68(13) . . . . ?
N11 C6 N9 N8 2.6(2) . . . . ?
N10 C6 N9 N8 -176.75(14) . . . . ?
C5 N8 N9 C6 -175.50(15) . . . . ?
C3 N7 O3 N6 0.34(17) . . . . ?
O4 N6 O3 N7 -178.65(15) . . . . ?
C2 N6 O3 N7 1.15(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 1017968'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N6 O2, C N5 O3'
_chemical_formula_sum            'C6 H9 N11 O5'
_chemical_formula_weight         315.24

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   11.3383(10)
_cell_length_b                   6.2879(5)
_cell_length_c                   18.1702(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.761(3)
_cell_angle_gamma                90.00
_cell_volume                     1252.67(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2129
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      25.03

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8397
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.44
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2294
_reflns_number_gt                1567
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2294
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1696(2) 0.6131(3) 0.18282(12) 0.0231(5) Uani 1 1 d . . .
C2 C 0.3284(2) 0.6088(3) 0.40033(13) 0.0263(5) Uani 1 1 d . . .
C3 C 0.32486(19) 0.5252(3) 0.47195(12) 0.0235(5) Uani 1 1 d . . .
C4 C 0.2953(2) 0.5206(4) 0.32227(13) 0.0421(7) Uani 1 1 d . . .
H4A H 0.2085 0.5462 0.2990 0.063 Uiso 1 1 calc R . .
H4B H 0.3113 0.3673 0.3243 0.063 Uiso 1 1 calc R . .
H4C H 0.3441 0.5900 0.2918 0.063 Uiso 1 1 calc R . .
C5 C 0.2709(2) 0.3275(3) 0.48930(12) 0.0253(5) Uani 1 1 d . . .
H5 H 0.2894 0.2741 0.5399 0.030 Uiso 1 1 calc R . .
C6 C 0.0683(2) -0.0629(3) 0.40068(12) 0.0249(5) Uani 1 1 d . . .
N1 N -0.26520(16) 0.5908(3) 0.12328(10) 0.0246(4) Uani 1 1 d . . .
N2 N -0.31441(17) 0.7837(3) 0.12272(10) 0.0267(5) Uani 1 1 d . . .
N3 N -0.25390(19) 0.9129(3) 0.17728(11) 0.0329(5) Uani 1 1 d . . .
N4 N -0.15906(18) 0.7994(3) 0.21656(10) 0.0310(5) Uani 1 1 d . . .
N5 N -0.08512(18) 0.4433(3) 0.21070(10) 0.0291(5) Uani 1 1 d . . .
N6 N 0.37727(18) 0.8003(3) 0.41382(11) 0.0321(5) Uani 1 1 d . . .
N7 N 0.37426(17) 0.6543(3) 0.52783(10) 0.0322(5) Uani 1 1 d . . .
N8 N 0.19821(16) 0.2272(3) 0.43536(9) 0.0220(4) Uani 1 1 d . . .
N9 N 0.14876(16) 0.0444(3) 0.45520(10) 0.0249(4) Uani 1 1 d . . .
H9 H 0.1691 -0.0019 0.5025 0.030 Uiso 1 1 calc R . .
N10 N 0.02383(18) -0.2425(3) 0.41980(11) 0.0341(5) Uani 1 1 d . . .
H10A H -0.0274 -0.3180 0.3851 0.041 Uiso 1 1 calc R . .
H10B H 0.0454 -0.2868 0.4673 0.041 Uiso 1 1 calc R . .
N11 N 0.03916(17) 0.0105(3) 0.33072(10) 0.0299(5) Uani 1 1 d . . .
H11A H -0.0118 -0.0608 0.2945 0.036 Uiso 1 1 calc R . .
H11B H 0.0706 0.1310 0.3200 0.036 Uiso 1 1 calc R . .
O1 O -0.41083(15) 0.8410(3) 0.07429(9) 0.0404(5) Uani 1 1 d . . .
O2 O -0.00411(15) 0.4778(3) 0.26880(9) 0.0385(4) Uani 1 1 d . . .
O3 O -0.09980(16) 0.2755(3) 0.17604(9) 0.0404(5) Uani 1 1 d . . .
O4 O 0.40983(15) 0.8325(2) 0.49586(9) 0.0375(4) Uani 1 1 d . . .
O5 O 0.39780(17) 0.9474(3) 0.37396(10) 0.0460(5) Uani 1 1 d . . .


_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 N4 1.314(3) . ?
C1 N1 1.329(3) . ?
C1 N5 1.438(3) . ?
C2 N6 1.322(3) . ?
C2 C3 1.414(3) . ?
C2 C4 1.479(3) . ?
C3 N7 1.309(3) . ?
C3 C5 1.455(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N8 1.275(3) . ?
C5 H5 0.9500 . ?
C6 N11 1.313(3) . ?
C6 N10 1.319(3) . ?
C6 N9 1.345(3) . ?
N1 N2 1.334(2) . ?
N2 O1 1.269(2) . ?
N2 N3 1.329(2) . ?
N3 N4 1.335(3) . ?
N5 O3 1.219(2) . ?
N5 O2 1.229(2) . ?
N6 O5 1.233(2) . ?
N6 O4 1.456(2) . ?
N7 O4 1.370(2) . ?
N8 N9 1.367(2) . ?
N9 H9 0.8800 . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 115.61(19) . . ?
N4 C1 N5 121.63(19) . . ?
N1 C1 N5 122.72(18) . . ?
N6 C2 C3 106.08(19) . . ?
N6 C2 C4 120.8(2) . . ?
C3 C2 C4 133.1(2) . . ?
N7 C3 C2 112.11(19) . . ?
N7 C3 C5 118.82(19) . . ?
C2 C3 C5 129.0(2) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N8 C5 C3 118.8(2) . . ?
N8 C5 H5 120.6 . . ?
C3 C5 H5 120.6 . . ?
N11 C6 N10 122.5(2) . . ?
N11 C6 N9 119.53(19) . . ?
N10 C6 N9 118.0(2) . . ?
C1 N1 N2 99.40(16) . . ?
O1 N2 N3 122.23(18) . . ?
O1 N2 N1 123.28(18) . . ?
N3 N2 N1 114.48(18) . . ?
N2 N3 N4 105.35(17) . . ?
C1 N4 N3 105.16(18) . . ?
O3 N5 O2 124.8(2) . . ?
O3 N5 C1 118.03(18) . . ?
O2 N5 C1 117.17(19) . . ?
O5 N6 C2 135.0(2) . . ?
O5 N6 O4 117.41(17) . . ?
C2 N6 O4 107.56(17) . . ?
C3 N7 O4 107.00(17) . . ?
C5 N8 N9 116.19(17) . . ?
C6 N9 N8 118.33(17) . . ?
C6 N9 H9 120.8 . . ?
N8 N9 H9 120.8 . . ?
C6 N10 H10A 120.0 . . ?
C6 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C6 N11 H11A 120.0 . . ?
C6 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
N7 O4 N6 107.17(14) . . ?

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
N6 C2 C3 N7 -2.8(3) . . . . ?
C4 C2 C3 N7 174.0(2) . . . . ?
N6 C2 C3 C5 174.4(2) . . . . ?
C4 C2 C3 C5 -8.8(4) . . . . ?
N7 C3 C5 N8 163.4(2) . . . . ?
C2 C3 C5 N8 -13.6(3) . . . . ?
N4 C1 N1 N2 0.0(2) . . . . ?
N5 C1 N1 N2 177.93(18) . . . . ?
C1 N1 N2 O1 179.92(19) . . . . ?
C1 N1 N2 N3 0.1(2) . . . . ?
O1 N2 N3 N4 -179.99(18) . . . . ?
N1 N2 N3 N4 -0.1(2) . . . . ?
N1 C1 N4 N3 -0.1(2) . . . . ?
N5 C1 N4 N3 -178.03(18) . . . . ?
N2 N3 N4 C1 0.1(2) . . . . ?
N4 C1 N5 O3 -179.22(19) . . . . ?
N1 C1 N5 O3 3.0(3) . . . . ?
N4 C1 N5 O2 1.9(3) . . . . ?
N1 C1 N5 O2 -175.88(19) . . . . ?
C3 C2 N6 O5 -176.3(2) . . . . ?
C4 C2 N6 O5 6.4(4) . . . . ?
C3 C2 N6 O4 2.6(2) . . . . ?
C4 C2 N6 O4 -174.7(2) . . . . ?
C2 C3 N7 O4 1.7(3) . . . . ?
C5 C3 N7 O4 -175.78(18) . . . . ?
C3 C5 N8 N9 -178.98(18) . . . . ?
N11 C6 N9 N8 -0.4(3) . . . . ?
N10 C6 N9 N8 177.96(18) . . . . ?
C5 N8 N9 C6 177.71(19) . . . . ?
C3 N7 O4 N6 -0.1(2) . . . . ?
O5 N6 O4 N7 177.40(18) . . . . ?
C2 N6 O4 N7 -1.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 1017969'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
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# 
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#  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.
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#  fide research purposes only. It may contain copyright material
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N6 O2, C3 H2 N7 O, H2 O'
_chemical_formula_sum            'C8 H13 N13 O4'
_chemical_formula_weight         355.31

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

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   9.3457(6)
_cell_length_b                   25.7804(17)
_cell_length_c                   13.4303(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.4145(19)
_cell_angle_gamma                90.00
_cell_volume                     3051.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3861
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      25.58

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18176
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         25.98
_reflns_number_total             5877
_reflns_number_gt                3640
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0405P)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         5877
_refine_ls_number_parameters     465
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7297(2) 0.43652(8) 0.52055(16) 0.0243(5) Uani 1 1 d . . .
C2 C 0.7728(2) 0.48099(8) 0.47218(15) 0.0218(5) Uani 1 1 d . . .
C3 C 0.8539(2) 0.48264(8) 0.39700(15) 0.0212(5) Uani 1 1 d . . .
C4 C 0.4435(2) 0.64754(8) 0.26997(17) 0.0283(5) Uani 1 1 d . . .
C5 C 0.4981(2) 0.68584(8) 0.21497(16) 0.0241(5) Uani 1 1 d . . .
C6 C 0.5718(2) 0.67677(8) 0.13579(16) 0.0232(5) Uani 1 1 d . . .
C7 C 0.3501(2) 0.58831(8) 0.85888(16) 0.0229(5) Uani 1 1 d . . .
C8 C 0.3746(2) 0.53414(8) 0.85953(15) 0.0208(5) Uani 1 1 d . . .
C9 C 0.2733(2) 0.62242(8) 0.91414(17) 0.0310(5) Uani 1 1 d . . .
H9A H 0.3094 0.6581 0.9141 0.046 Uiso 1 1 calc R . .
H9B H 0.2964 0.6105 0.9871 0.046 Uiso 1 1 calc R . .
H9C H 0.1635 0.6212 0.8778 0.046 Uiso 1 1 calc R . .
C10 C 0.3300(2) 0.49310(8) 0.91784(16) 0.0240(5) Uani 1 1 d . . .
H10 H 0.3497 0.4580 0.9052 0.029 Uiso 1 1 calc R . .
C11 C 1.0614(2) 0.72739(9) 0.16719(17) 0.0307(5) Uani 1 1 d . . .
C12 C 1.0375(2) 0.67337(9) 0.17493(17) 0.0291(5) Uani 1 1 d . . .
C13 C 1.0403(3) 0.77269(9) 0.2281(2) 0.0466(7) Uani 1 1 d . . .
H13A H 1.0900 0.8030 0.2100 0.070 Uiso 1 1 calc R . .
H13B H 1.0854 0.7654 0.3038 0.070 Uiso 1 1 calc R . .
H13C H 0.9317 0.7797 0.2109 0.070 Uiso 1 1 calc R . .
C14 C 0.9802(2) 0.64550(9) 0.24733(17) 0.0297(5) Uani 1 1 d . . .
H14 H 0.9831 0.6087 0.2490 0.036 Uiso 1 1 calc R . .
C15 C 0.8083(2) 0.66399(8) 0.43790(17) 0.0269(5) Uani 1 1 d . . .
C23 C 0.1625(2) 0.46769(8) 1.10775(16) 0.0221(5) Uani 1 1 d . . .
N1 N 0.6624(2) 0.45268(7) 0.58616(14) 0.0316(5) Uani 1 1 d . . .
N2 N 0.72935(19) 0.52281(7) 0.50850(14) 0.0296(4) Uani 1 1 d . . .
N3 N 0.7539(2) 0.38608(7) 0.50445(15) 0.0382(5) Uani 1 1 d . . .
H3A H 0.7239 0.3618 0.5391 0.046 Uiso 1 1 calc R . .
H3B H 0.7998 0.3775 0.4593 0.046 Uiso 1 1 calc R . .
N4 N 0.90237(18) 0.43993(7) 0.36192(13) 0.0249(4) Uani 1 1 d . . .
N5 N 0.97166(19) 0.45797(7) 0.29566(13) 0.0267(4) Uani 1 1 d . . .
N6 N 0.96478(19) 0.50940(7) 0.29192(13) 0.0264(4) Uani 1 1 d . . .
N7 N 0.89064(19) 0.52648(7) 0.35589(13) 0.0249(4) Uani 1 1 d . . .
N8 N 0.3877(2) 0.67050(7) 0.33609(15) 0.0339(5) Uani 1 1 d . . .
N9 N 0.4754(2) 0.73175(7) 0.24686(14) 0.0335(5) Uani 1 1 d . . .
N10 N 0.4443(2) 0.59583(7) 0.25501(17) 0.0535(6) Uani 1 1 d . . .
H10A H 0.4054 0.5749 0.2910 0.064 Uiso 1 1 calc R . .
H10B H 0.4838 0.5830 0.2092 0.064 Uiso 1 1 calc R . .
N11 N 0.60567(18) 0.62905(7) 0.11169(13) 0.0261(4) Uani 1 1 d . . .
N12 N 0.6691(2) 0.63683(7) 0.03629(14) 0.0287(4) Uani 1 1 d . . .
N13 N 0.6720(2) 0.68709(7) 0.01741(14) 0.0321(5) Uani 1 1 d . . .
N14 N 0.6109(2) 0.71343(7) 0.07943(14) 0.0305(4) Uani 1 1 d . . .
N15 N 0.4092(2) 0.60753(7) 0.79004(14) 0.0292(4) Uani 1 1 d . . .
N16 N 0.44759(19) 0.52023(7) 0.79522(13) 0.0264(4) Uani 1 1 d . . .
N17 N 0.26527(18) 0.50324(6) 0.98542(13) 0.0222(4) Uani 1 1 d . . .
N18 N 0.22953(18) 0.46050(6) 1.03395(12) 0.0233(4) Uani 1 1 d . . .
H18 H 0.2500 0.4290 1.0171 0.028 Uiso 1 1 calc R . .
N19 N 0.13076(19) 0.51518(6) 1.13088(13) 0.0282(4) Uani 1 1 d . . .
H19A H 0.0848 0.5200 1.1777 0.034 Uiso 1 1 calc R . .
H19B H 0.1556 0.5420 1.0995 0.034 Uiso 1 1 calc R . .
N20 N 0.12698(19) 0.42687(7) 1.15306(13) 0.0289(4) Uani 1 1 d . . .
H20A H 0.0809 0.4308 1.2001 0.035 Uiso 1 1 calc R . .
H20B H 0.1492 0.3956 1.1364 0.035 Uiso 1 1 calc R . .
N21 N 1.1156(2) 0.73321(8) 0.08859(15) 0.0380(5) Uani 1 1 d . . .
N22 N 1.0759(2) 0.64642(8) 0.10431(15) 0.0398(5) Uani 1 1 d . . .
N23 N 0.9254(2) 0.67023(7) 0.30920(14) 0.0274(4) Uani 1 1 d . . .
N24 N 0.87220(19) 0.64010(7) 0.37398(13) 0.0300(4) Uani 1 1 d . . .
H24 H 0.8798 0.6061 0.3736 0.036 Uiso 1 1 calc R . .
N25 N 0.7994(2) 0.71507(7) 0.43780(14) 0.0326(5) Uani 1 1 d . . .
H25A H 0.7580 0.7308 0.4796 0.039 Uiso 1 1 calc R . .
H25B H 0.8348 0.7334 0.3959 0.039 Uiso 1 1 calc R . .
N26 N 0.7567(2) 0.63556(7) 0.49923(14) 0.0362(5) Uani 1 1 d . . .
H26A H 0.7148 0.6505 0.5417 0.043 Uiso 1 1 calc R . .
H26B H 0.7638 0.6015 0.4980 0.043 Uiso 1 1 calc R . .
O1 O 0.66182(17) 0.50693(6) 0.57992(12) 0.0361(4) Uani 1 1 d . . .
O2 O 0.40734(17) 0.72383(6) 0.32198(12) 0.0358(4) Uani 1 1 d . . .
O3 O 0.47465(16) 0.56489(6) 0.74836(11) 0.0304(4) Uani 1 1 d . . .
O4 O 0.41745(19) 0.65146(6) 0.75513(13) 0.0440(5) Uani 1 1 d . . .
O5 O 1.12618(19) 0.68152(7) 0.04601(13) 0.0458(5) Uani 1 1 d . . .
O6 O 1.15684(19) 0.76996(7) 0.04585(14) 0.0533(5) Uani 1 1 d . . .
O7 O 0.3995(2) 0.31995(6) 0.37466(15) 0.0410(5) Uani 1 1 d D . .
H7A H 0.409(3) 0.2882(6) 0.3894(19) 0.049 Uiso 1 1 d D . .
H7B H 0.476(2) 0.3294(9) 0.362(2) 0.049 Uiso 1 1 d D . .
O8 O 0.2138(2) 0.32090(7) 0.15781(14) 0.0416(5) Uani 1 1 d D . .
H8A H 0.267(2) 0.3177(10) 0.1194(16) 0.050 Uiso 1 1 d D . .
H8B H 0.271(2) 0.3187(10) 0.2193(13) 0.050 Uiso 1 1 d D . .


_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 N1 1.309(3) . ?
C1 N3 1.350(3) . ?
C1 C2 1.440(3) . ?
C2 N2 1.303(3) . ?
C2 C3 1.450(3) . ?
C3 N4 1.335(3) . ?
C3 N7 1.351(2) . ?
C4 N8 1.311(3) . ?
C4 N10 1.349(3) . ?
C4 C5 1.425(3) . ?
C5 N9 1.300(3) . ?
C5 C6 1.465(3) . ?
C6 N14 1.335(3) . ?
C6 N11 1.337(3) . ?
C7 N15 1.321(3) . ?
C7 C8 1.415(3) . ?
C7 C9 1.481(3) . ?
C8 N16 1.316(2) . ?
C8 C10 1.457(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N17 1.274(3) . ?
C10 H10 0.9500 . ?
C11 N21 1.323(3) . ?
C11 C12 1.420(3) . ?
C11 C13 1.476(3) . ?
C12 N22 1.318(3) . ?
C12 C14 1.448(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N23 1.281(3) . ?
C14 H14 0.9500 . ?
C15 N26 1.309(3) . ?
C15 N25 1.319(3) . ?
C15 N24 1.347(3) . ?
C23 N20 1.312(3) . ?
C23 N19 1.321(3) . ?
C23 N18 1.350(3) . ?
N1 O1 1.401(2) . ?
N2 O1 1.374(2) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 N5 1.346(2) . ?
N5 N6 1.328(2) . ?
N6 N7 1.345(2) . ?
N8 O2 1.408(2) . ?
N9 O2 1.375(2) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N11 N12 1.348(2) . ?
N12 N13 1.322(2) . ?
N13 N14 1.341(2) . ?
N15 O4 1.238(2) . ?
N15 O3 1.457(2) . ?
N16 O3 1.376(2) . ?
N17 N18 1.377(2) . ?
N18 H18 0.8800 . ?
N19 H19A 0.8800 . ?
N19 H19B 0.8800 . ?
N20 H20A 0.8800 . ?
N20 H20B 0.8800 . ?
N21 O6 1.234(2) . ?
N21 O5 1.466(2) . ?
N22 O5 1.377(2) . ?
N23 N24 1.376(2) . ?
N24 H24 0.8800 . ?
N25 H25A 0.8800 . ?
N25 H25B 0.8800 . ?
N26 H26A 0.8800 . ?
N26 H26B 0.8800 . ?
O7 H7A 0.839(15) . ?
O7 H7B 0.824(15) . ?
O8 H8A 0.828(16) . ?
O8 H8B 0.822(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
N1 C1 N3 123.9(2) . . ?
N1 C1 C2 108.63(19) . . ?
N3 C1 C2 127.43(19) . . ?
N2 C2 C1 108.73(18) . . ?
N2 C2 C3 122.44(19) . . ?
C1 C2 C3 128.82(19) . . ?
N4 C3 N7 112.55(18) . . ?
N4 C3 C2 122.59(18) . . ?
N7 C3 C2 124.86(19) . . ?
N8 C4 N10 124.8(2) . . ?
N8 C4 C5 109.26(19) . . ?
N10 C4 C5 125.9(2) . . ?
N9 C5 C4 109.51(19) . . ?
N9 C5 C6 123.54(19) . . ?
C4 C5 C6 126.95(19) . . ?
N14 C6 N11 112.51(18) . . ?
N14 C6 C5 125.55(19) . . ?
N11 C6 C5 121.94(18) . . ?
N15 C7 C8 105.68(18) . . ?
N15 C7 C9 120.86(19) . . ?
C8 C7 C9 133.42(19) . . ?
N16 C8 C7 112.53(18) . . ?
N16 C8 C10 117.26(19) . . ?
C7 C8 C10 130.20(19) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N17 C10 C8 121.49(19) . . ?
N17 C10 H10 119.3 . . ?
C8 C10 H10 119.3 . . ?
N21 C11 C12 106.3(2) . . ?
N21 C11 C13 120.6(2) . . ?
C12 C11 C13 133.1(2) . . ?
N22 C12 C11 112.2(2) . . ?
N22 C12 C14 118.2(2) . . ?
C11 C12 C14 129.7(2) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N23 C14 C12 120.4(2) . . ?
N23 C14 H14 119.8 . . ?
C12 C14 H14 119.8 . . ?
N26 C15 N25 121.6(2) . . ?
N26 C15 N24 118.6(2) . . ?
N25 C15 N24 119.8(2) . . ?
N20 C23 N19 121.54(19) . . ?
N20 C23 N18 118.76(19) . . ?
N19 C23 N18 119.68(19) . . ?
C1 N1 O1 105.70(16) . . ?
C2 N2 O1 106.70(16) . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C3 N4 N5 104.05(16) . . ?
N6 N5 N4 110.02(16) . . ?
N5 N6 N7 109.37(16) . . ?
N6 N7 C3 104.02(17) . . ?
C4 N8 O2 104.51(17) . . ?
C5 N9 O2 105.83(17) . . ?
C4 N10 H10A 120.0 . . ?
C4 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C6 N11 N12 104.11(16) . . ?
N13 N12 N11 109.40(17) . . ?
N12 N13 N14 109.68(16) . . ?
C6 N14 N13 104.30(17) . . ?
O4 N15 C7 134.55(19) . . ?
O4 N15 O3 117.23(16) . . ?
C7 N15 O3 108.21(16) . . ?
C8 N16 O3 106.64(16) . . ?
C10 N17 N18 114.87(17) . . ?
C23 N18 N17 118.86(17) . . ?
C23 N18 H18 120.6 . . ?
N17 N18 H18 120.6 . . ?
C23 N19 H19A 120.0 . . ?
C23 N19 H19B 120.0 . . ?
H19A N19 H19B 120.0 . . ?
C23 N20 H20A 120.0 . . ?
C23 N20 H20B 120.0 . . ?
H20A N20 H20B 120.0 . . ?
O6 N21 C11 136.1(2) . . ?
O6 N21 O5 116.37(18) . . ?
C11 N21 O5 107.56(18) . . ?
C12 N22 O5 106.78(19) . . ?
C14 N23 N24 115.81(19) . . ?
C15 N24 N23 118.35(18) . . ?
C15 N24 H24 120.8 . . ?
N23 N24 H24 120.8 . . ?
C15 N25 H25A 120.0 . . ?
C15 N25 H25B 120.0 . . ?
H25A N25 H25B 120.0 . . ?
C15 N26 H26A 120.0 . . ?
C15 N26 H26B 120.0 . . ?
H26A N26 H26B 120.0 . . ?
N2 O1 N1 110.22(14) . . ?
N9 O2 N8 110.90(15) . . ?
N16 O3 N15 106.93(13) . . ?
N22 O5 N21 107.17(15) . . ?
H7A O7 H7B 108(2) . . ?
H8A O8 H8B 107(2) . . ?

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
N1 C1 C2 N2 -0.7(2) . . . . ?
N3 C1 C2 N2 -179.9(2) . . . . ?
N1 C1 C2 C3 177.98(19) . . . . ?
N3 C1 C2 C3 -1.2(4) . . . . ?
N2 C2 C3 N4 178.0(2) . . . . ?
C1 C2 C3 N4 -0.5(3) . . . . ?
N2 C2 C3 N7 -1.0(3) . . . . ?
C1 C2 C3 N7 -179.6(2) . . . . ?
N8 C4 C5 N9 -0.2(3) . . . . ?
N10 C4 C5 N9 178.0(2) . . . . ?
N8 C4 C5 C6 178.67(19) . . . . ?
N10 C4 C5 C6 -3.1(4) . . . . ?
N9 C5 C6 N14 -6.9(3) . . . . ?
C4 C5 C6 N14 174.3(2) . . . . ?
N9 C5 C6 N11 173.9(2) . . . . ?
C4 C5 C6 N11 -4.9(3) . . . . ?
N15 C7 C8 N16 0.9(2) . . . . ?
C9 C7 C8 N16 178.7(2) . . . . ?
N15 C7 C8 C10 -178.03(19) . . . . ?
C9 C7 C8 C10 -0.2(4) . . . . ?
N16 C8 C10 N17 176.70(18) . . . . ?
C7 C8 C10 N17 -4.4(3) . . . . ?
N21 C11 C12 N22 0.3(3) . . . . ?
C13 C11 C12 N22 -178.3(2) . . . . ?
N21 C11 C12 C14 179.9(2) . . . . ?
C13 C11 C12 C14 1.3(4) . . . . ?
N22 C12 C14 N23 -172.0(2) . . . . ?
C11 C12 C14 N23 8.4(4) . . . . ?
N3 C1 N1 O1 179.38(19) . . . . ?
C2 C1 N1 O1 0.2(2) . . . . ?
C1 C2 N2 O1 1.0(2) . . . . ?
C3 C2 N2 O1 -177.86(17) . . . . ?
N7 C3 N4 N5 -0.3(2) . . . . ?
C2 C3 N4 N5 -179.49(17) . . . . ?
C3 N4 N5 N6 0.2(2) . . . . ?
N4 N5 N6 N7 0.0(2) . . . . ?
N5 N6 N7 C3 -0.2(2) . . . . ?
N4 C3 N7 N6 0.3(2) . . . . ?
C2 C3 N7 N6 179.49(18) . . . . ?
N10 C4 N8 O2 -178.1(2) . . . . ?
C5 C4 N8 O2 0.1(2) . . . . ?
C4 C5 N9 O2 0.2(2) . . . . ?
C6 C5 N9 O2 -178.73(17) . . . . ?
N14 C6 N11 N12 0.0(2) . . . . ?
C5 C6 N11 N12 179.28(18) . . . . ?
C6 N11 N12 N13 0.0(2) . . . . ?
N11 N12 N13 N14 -0.1(2) . . . . ?
N11 C6 N14 N13 0.0(2) . . . . ?
C5 C6 N14 N13 -179.29(19) . . . . ?
N12 N13 N14 C6 0.1(2) . . . . ?
C8 C7 N15 O4 177.6(2) . . . . ?
C9 C7 N15 O4 -0.6(4) . . . . ?
C8 C7 N15 O3 -1.2(2) . . . . ?
C9 C7 N15 O3 -179.36(17) . . . . ?
C7 C8 N16 O3 -0.2(2) . . . . ?
C10 C8 N16 O3 178.90(16) . . . . ?
C8 C10 N17 N18 179.83(17) . . . . ?
N20 C23 N18 N17 179.25(17) . . . . ?
N19 C23 N18 N17 0.9(3) . . . . ?
C10 N17 N18 C23 179.11(18) . . . . ?
C12 C11 N21 O6 -179.9(2) . . . . ?
C13 C11 N21 O6 -1.1(4) . . . . ?
C12 C11 N21 O5 -0.1(2) . . . . ?
C13 C11 N21 O5 178.74(19) . . . . ?
C11 C12 N22 O5 -0.4(3) . . . . ?
C14 C12 N22 O5 180.00(18) . . . . ?
C12 C14 N23 N24 179.23(18) . . . . ?
N26 C15 N24 N23 179.60(18) . . . . ?
N25 C15 N24 N23 -0.6(3) . . . . ?
C14 N23 N24 C15 -177.59(19) . . . . ?
C2 N2 O1 N1 -0.9(2) . . . . ?
C1 N1 O1 N2 0.4(2) . . . . ?
C5 N9 O2 N8 -0.1(2) . . . . ?
C4 N8 O2 N9 0.0(2) . . . . ?
C8 N16 O3 N15 -0.55(19) . . . . ?
O4 N15 O3 N16 -177.90(17) . . . . ?
C7 N15 O3 N16 1.1(2) . . . . ?
C12 N22 O5 N21 0.3(2) . . . . ?
O6 N21 O5 N22 179.76(18) . . . . ?
C11 N21 O5 N22 -0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 1017970'
