# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_bn3425
_database_code_depnum_ccdc_archive 'CCDC 1483054'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H8 N6 O2'
_chemical_formula_weight         148.14

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   9.280(3)
_cell_length_b                   4.5988(16)
_cell_length_c                   14.376(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     613.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2427
_cell_measurement_theta_min      2.185
_cell_measurement_theta_max      31,461

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6776
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         31.50
_reflns_number_total             1923
_reflns_number_gt                1829
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.0980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.4(13)
_refine_ls_number_reflns         1923
_refine_ls_number_parameters     124
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.08554(10) 0.5203(2) 0.56585(7) 0.0198(2) Uani 1 1 d . . .
O2 O 0.62632(10) 0.5314(2) 0.74646(7) 0.0201(2) Uani 1 1 d . . .
N1 N 0.24030(15) 0.8960(3) 0.45393(9) 0.0271(3) Uani 1 1 d . . .
N2 N 0.29906(13) 0.7327(2) 0.52806(9) 0.0225(2) Uani 1 1 d . . .
N3 N 0.28178(12) 0.4144(2) 0.65210(8) 0.0175(2) Uani 1 1 d . . .
N4 N 0.43056(12) 0.4156(2) 0.66129(8) 0.0175(2) Uani 1 1 d . . .
N5 N 0.41399(12) 0.7576(2) 0.77839(9) 0.0199(2) Uani 1 1 d . . .
N6 N 0.47267(14) 0.9460(3) 0.84578(9) 0.0234(3) Uani 1 1 d . . .
C1 C 0.21665(13) 0.5567(3) 0.57989(9) 0.0161(2) Uani 1 1 d . . .
C2 C 0.49562(13) 0.5684(2) 0.73120(9) 0.0155(2) Uani 1 1 d . . .
H5 H 0.3247(18) 0.771(4) 0.7650(13) 0.019(4) Uiso 1 1 d . . .
H2 H 0.3871(19) 0.759(4) 0.5380(16) 0.023(5) Uiso 1 1 d . . .
H3 H 0.232(2) 0.280(4) 0.6825(13) 0.025(4) Uiso 1 1 d . . .
H1A H 0.1764(19) 1.022(4) 0.4778(15) 0.024(4) Uiso 1 1 d . . .
H1B H 0.194(2) 0.771(5) 0.4163(15) 0.037(5) Uiso 1 1 d . . .
H4 H 0.481(2) 0.272(4) 0.6391(14) 0.034(5) Uiso 1 1 d . . .
H6A H 0.506(2) 0.836(5) 0.8919(19) 0.052(6) Uiso 1 1 d . . .
H6B H 0.552(2) 1.025(5) 0.8246(17) 0.044(6) Uiso 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
O1 C1 1.2447(16) . ?
O2 C2 1.2442(16) . ?
N1 N2 1.4133(17) . ?
N1 H1A 0.897(18) . ?
N1 H1B 0.90(2) . ?
N2 C1 1.3397(17) . ?
N2 H2 0.838(18) . ?
N3 C1 1.3681(17) . ?
N3 N4 1.3870(14) . ?
N3 H3 0.89(2) . ?
N4 C2 1.3670(16) . ?
N4 H4 0.87(2) . ?
N5 C2 1.3384(17) . ?
N5 N6 1.4090(17) . ?
N5 H5 0.853(17) . ?
N6 H6A 0.89(3) . ?
N6 H6B 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1A 108.0(13) . . ?
N2 N1 H1B 107.3(14) . . ?
H1A N1 H1B 109.3(17) . . ?
C1 N2 N1 121.34(12) . . ?
C1 N2 H2 123.2(14) . . ?
N1 N2 H2 115.4(14) . . ?
C1 N3 N4 120.67(10) . . ?
C1 N3 H3 118.5(12) . . ?
N4 N3 H3 118.4(12) . . ?
C2 N4 N3 120.78(10) . . ?
C2 N4 H4 115.2(13) . . ?
N3 N4 H4 119.6(13) . . ?
C2 N5 N6 121.97(11) . . ?
C2 N5 H5 118.9(12) . . ?
N6 N5 H5 119.1(12) . . ?
N5 N6 H6A 107.3(15) . . ?
N5 N6 H6B 109.9(16) . . ?
H6A N6 H6B 101.7(18) . . ?
O1 C1 N2 123.31(12) . . ?
O1 C1 N3 119.37(11) . . ?
N2 C1 N3 117.32(11) . . ?
O2 C2 N5 123.46(12) . . ?
O2 C2 N4 119.33(11) . . ?
N5 C2 N4 117.19(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
C1 N3 N4 C2 109.44(12) . . . . ?
N1 N2 C1 O1 1.4(2) . . . . ?
N1 N2 C1 N3 -177.90(12) . . . . ?
N4 N3 C1 O1 170.32(11) . . . . ?
N4 N3 C1 N2 -10.33(17) . . . . ?
N6 N5 C2 O2 4.4(2) . . . . ?
N6 N5 C2 N4 -173.92(12) . . . . ?
N3 N4 C2 O2 169.26(11) . . . . ?
N3 N4 C2 N5 -12.39(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        31.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042


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

data_bn3426
_database_code_depnum_ccdc_archive 'CCDC 1483055'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 N9 O9'
_chemical_formula_weight         377.26

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   4.6017(14)
_cell_length_b                   25.268(8)
_cell_length_c                   11.950(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.11
_cell_angle_gamma                90.00
_cell_volume                     1378.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5081
_cell_measurement_theta_min      2.356
_cell_measurement_theta_max      31.502

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16876
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         31.54
_reflns_number_total             4588
_reflns_number_gt                3374
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0695P)²+0.1950P] 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         4588
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7711(3) 0.54996(5) 0.48238(10) 0.0197(3) Uani 1 1 d . . .
O2 O 0.9924(3) 0.52037(5) 0.15097(10) 0.0221(3) Uani 1 1 d . . .
O3 O 0.8041(3) 0.65585(5) 0.32646(11) 0.0202(3) Uani 1 1 d . . .
O4 O 0.4759(4) 0.70207(5) 0.46897(12) 0.0330(4) Uani 1 1 d . . .
O5 O 0.3678(3) 0.78429(6) 0.44854(13) 0.0338(4) Uani 1 1 d . . .
O6 O 0.8323(3) 0.89832(5) 0.21217(11) 0.0237(3) Uani 1 1 d . . .
O7 O 1.1598(3) 0.86638(5) 0.11480(12) 0.0268(3) Uani 1 1 d . . .
O8 O 0.9275(3) 0.65919(6) 0.03837(12) 0.0318(3) Uani 1 1 d . . .
O9 O 1.2675(4) 0.64476(6) 0.17507(13) 0.0396(4) Uani 1 1 d . . .
N1 N 0.3125(3) 0.59931(6) 0.39142(13) 0.0176(3) Uani 1 1 d . . .
N2 N 0.4048(3) 0.55303(6) 0.33841(13) 0.0186(3) Uani 1 1 d . . .
N3 N 0.7694(3) 0.48986(6) 0.34171(12) 0.0175(3) Uani 1 1 d . . .
N4 N 0.6537(3) 0.47266(6) 0.23577(12) 0.0168(3) Uani 1 1 d . . .
N5 N 0.7355(3) 0.45516(6) 0.05373(13) 0.0217(3) Uani 1 1 d . . .
N6 N 0.5286(4) 0.41375(7) 0.05360(15) 0.0260(3) Uani 1 1 d . . .
N7 N 0.5001(3) 0.74478(6) 0.42250(12) 0.0186(3) Uani 1 1 d . . .
N8 N 0.9638(3) 0.86073(5) 0.17579(12) 0.0181(3) Uani 1 1 d . . .
N9 N 1.0584(3) 0.66970(6) 0.13082(12) 0.0179(3) Uani 1 1 d . . .
C1 C 0.6555(3) 0.53158(6) 0.39194(13) 0.0141(3) Uani 1 1 d . . .
C2 C 0.8063(4) 0.48414(6) 0.14713(14) 0.0166(3) Uani 1 1 d . . .
C3 C 0.8124(3) 0.70261(6) 0.28939(14) 0.0158(3) Uani 1 1 d . . .
C4 C 0.6826(3) 0.74912(6) 0.33256(14) 0.0158(3) Uani 1 1 d . . .
C5 C 0.7268(4) 0.80031(6) 0.29443(14) 0.0163(3) Uani 1 1 d . . .
H5 H 0.6415 0.8298 0.3275 0.020 Uiso 1 1 calc R . .
C6 C 0.8951(4) 0.80761(6) 0.20836(14) 0.0164(3) Uani 1 1 d . . .
C7 C 1.0067(4) 0.76468(7) 0.15295(14) 0.0178(3) Uani 1 1 d . . .
H7 H 1.1125 0.7699 0.0904 0.021 Uiso 1 1 calc R . .
C8 C 0.9580(4) 0.71519(6) 0.19199(14) 0.0166(3) Uani 1 1 d . . .
H5 H 0.809(5) 0.4614(10) -0.008(2) 0.035(7) Uiso 1 1 d . . .
H3 H 0.919(5) 0.4722(9) 0.3778(19) 0.027(6) Uiso 1 1 d . . .
H1B H 0.133(5) 0.6114(9) 0.350(2) 0.032(6) Uiso 1 1 d . . .
H6B H 0.615(5) 0.3854(10) 0.027(2) 0.029(6) Uiso 1 1 d . . .
H2 H 0.295(6) 0.5421(10) 0.283(2) 0.040(7) Uiso 1 1 d . . .
H4 H 0.551(5) 0.4459(10) 0.2348(19) 0.029(6) Uiso 1 1 d . . .
H1C H 0.282(5) 0.5926(9) 0.469(2) 0.034(6) Uiso 1 1 d . . .
H6A H 0.373(6) 0.4221(11) 0.006(2) 0.045(8) Uiso 1 1 d . . .
H1A H 0.461(5) 0.6257(10) 0.397(2) 0.033(6) Uiso 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
O1 C1 1.235(2) . ?
O2 C2 1.250(2) . ?
O3 C3 1.264(2) . ?
O4 N7 1.2252(19) . ?
O5 N7 1.229(2) . ?
O6 N8 1.2338(18) . ?
O7 N8 1.2362(19) . ?
O8 N9 1.2203(19) . ?
O9 N9 1.215(2) . ?
N1 N2 1.4196(19) . ?
N1 H1B 0.96(2) . ?
N1 H1C 0.97(2) . ?
N1 H1A 0.95(2) . ?
N2 C1 1.361(2) . ?
N2 H2 0.83(3) . ?
N3 C1 1.351(2) . ?
N3 N4 1.3812(19) . ?
N3 H3 0.89(2) . ?
N4 C2 1.372(2) . ?
N4 H4 0.82(2) . ?
N5 C2 1.341(2) . ?
N5 N6 1.415(2) . ?
N5 H5 0.87(3) . ?
N6 H6B 0.90(2) . ?
N6 H6A 0.88(3) . ?
N7 C4 1.448(2) . ?
N8 C6 1.444(2) . ?
N9 C8 1.467(2) . ?
C3 C4 1.442(2) . ?
C3 C8 1.448(2) . ?
C4 C5 1.394(2) . ?
C5 C6 1.374(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(2) . ?
C7 C8 1.363(2) . ?
C7 H7 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
N2 N1 H1B 108.4(14) . . ?
N2 N1 H1C 111.7(14) . . ?
H1B N1 H1C 109.6(19) . . ?
N2 N1 H1A 110.8(15) . . ?
H1B N1 H1A 112(2) . . ?
H1C N1 H1A 104(2) . . ?
C1 N2 N1 113.66(14) . . ?
C1 N2 H2 129.7(18) . . ?
N1 N2 H2 116.5(18) . . ?
C1 N3 N4 121.76(14) . . ?
C1 N3 H3 119.8(14) . . ?
N4 N3 H3 118.4(14) . . ?
C2 N4 N3 117.70(14) . . ?
C2 N4 H4 120.7(16) . . ?
N3 N4 H4 115.2(16) . . ?
C2 N5 N6 119.93(15) . . ?
C2 N5 H5 122.1(16) . . ?
N6 N5 H5 118.0(16) . . ?
N5 N6 H6B 105.3(15) . . ?
N5 N6 H6A 108.4(18) . . ?
H6B N6 H6A 109(2) . . ?
O4 N7 O5 121.67(15) . . ?
O4 N7 C4 119.80(14) . . ?
O5 N7 C4 118.52(14) . . ?
O6 N8 O7 122.97(14) . . ?
O6 N8 C6 119.18(14) . . ?
O7 N8 C6 117.81(14) . . ?
O9 N9 O8 123.81(16) . . ?
O9 N9 C8 118.08(14) . . ?
O8 N9 C8 118.10(14) . . ?
O1 C1 N3 122.26(15) . . ?
O1 C1 N2 120.68(15) . . ?
N3 C1 N2 117.06(14) . . ?
O2 C2 N5 121.67(16) . . ?
O2 C2 N4 122.68(15) . . ?
N5 C2 N4 115.60(15) . . ?
O3 C3 C4 127.20(15) . . ?
O3 C3 C8 121.59(15) . . ?
C4 C3 C8 111.20(14) . . ?
C5 C4 C3 123.75(15) . . ?
C5 C4 N7 115.73(14) . . ?
C3 C4 N7 120.50(14) . . ?
C6 C5 C4 119.16(15) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 121.56(15) . . ?
C5 C6 N8 119.28(14) . . ?
C7 C6 N8 119.15(14) . . ?
C8 C7 C6 117.59(15) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C7 C8 C3 126.04(15) . . ?
C7 C8 N9 118.24(15) . . ?
C3 C8 N9 115.71(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
C1 N3 N4 C2 105.17(18) . . . . ?
N4 N3 C1 O1 -173.98(15) . . . . ?
N4 N3 C1 N2 6.0(2) . . . . ?
N1 N2 C1 O1 5.0(2) . . . . ?
N1 N2 C1 N3 -175.00(14) . . . . ?
N6 N5 C2 O2 178.61(17) . . . . ?
N6 N5 C2 N4 -3.7(2) . . . . ?
N3 N4 C2 O2 -20.2(2) . . . . ?
N3 N4 C2 N5 162.18(15) . . . . ?
O3 C3 C4 C5 173.10(16) . . . . ?
C8 C3 C4 C5 -8.0(2) . . . . ?
O3 C3 C4 N7 -5.3(3) . . . . ?
C8 C3 C4 N7 173.56(14) . . . . ?
O4 N7 C4 C5 -172.22(16) . . . . ?
O5 N7 C4 C5 9.3(2) . . . . ?
O4 N7 C4 C3 6.3(2) . . . . ?
O5 N7 C4 C3 -172.14(16) . . . . ?
C3 C4 C5 C6 2.2(3) . . . . ?
N7 C4 C5 C6 -179.32(15) . . . . ?
C4 C5 C6 C7 4.4(3) . . . . ?
C4 C5 C6 N8 -174.27(15) . . . . ?
O6 N8 C6 C5 -11.9(2) . . . . ?
O7 N8 C6 C5 165.97(16) . . . . ?
O6 N8 C6 C7 169.39(16) . . . . ?
O7 N8 C6 C7 -12.7(2) . . . . ?
C5 C6 C7 C8 -4.0(3) . . . . ?
N8 C6 C7 C8 174.68(15) . . . . ?
C6 C7 C8 C3 -3.1(3) . . . . ?
C6 C7 C8 N9 176.47(15) . . . . ?
O3 C3 C8 C7 -172.43(17) . . . . ?
C4 C3 C8 C7 8.6(2) . . . . ?
O3 C3 C8 N9 8.0(2) . . . . ?
C4 C3 C8 N9 -170.95(13) . . . . ?
O9 N9 C8 C7 108.5(2) . . . . ?
O8 N9 C8 C7 -71.3(2) . . . . ?
O9 N9 C8 C3 -71.9(2) . . . . ?
O8 N9 C8 C3 108.32(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        31.54
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.065


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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1483056'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 N12 O23'
_chemical_formula_weight         728.45

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.324(2)
_cell_length_b                   9.2938(19)
_cell_length_c                   29.738(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.37(3)
_cell_angle_gamma                90.00
_cell_volume                     2815.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    8450
_cell_measurement_theta_min      1.9993
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.7302
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20334
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         27.49
_reflns_number_total             6415
_reflns_number_gt                5704
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0950P)²+3.4378P] 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         6415
_refine_ls_number_parameters     464
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.2002
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.207
_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
O1 O -0.2378(3) 1.0769(3) 0.12257(9) 0.0365(6) Uani 1 1 d . . .
O2 O -0.1499(3) 0.8975(3) 0.09206(10) 0.0375(6) Uani 1 1 d . . .
O3 O 0.0252(2) 1.1925(2) 0.15252(8) 0.0259(5) Uani 1 1 d . . .
O4 O 0.1609(3) 1.4412(3) 0.15314(8) 0.0351(6) Uani 1 1 d . . .
O5 O 0.2570(3) 1.4721(3) 0.09454(8) 0.0376(6) Uani 1 1 d . . .
O6 O 0.0144(3) 1.3618(3) -0.05205(9) 0.0336(6) Uani 1 1 d . . .
O7 O -0.1195(3) 1.1807(3) -0.06120(8) 0.0362(6) Uani 1 1 d . . .
O8 O -0.1871(2) 1.0507(3) 0.00714(8) 0.0304(5) Uani 1 1 d . . .
H8B H -0.1853 1.0631 -0.0207 0.046 Uiso 1 1 calc R . .
O9 O -0.4219(2) 1.2175(3) 0.42590(8) 0.0319(6) Uani 1 1 d . . .
O10 O -0.5546(2) 1.3883(2) 0.43820(8) 0.0271(5) Uani 1 1 d . . .
O11 O -0.6951(3) 1.4401(3) 0.58134(9) 0.0392(7) Uani 1 1 d . A .
O12 O -0.5672(17) 1.375(2) 0.6418(3) 0.048(3) Uani 0.68(5) 1 d PU A 1
O13 O -0.4207(2) 1.1342(2) 0.63516(7) 0.0240(5) Uani 1 1 d . A .
O14 O -0.2866(3) 0.8756(3) 0.57066(9) 0.0338(6) Uani 1 1 d . . .
O15 O -0.1722(2) 1.0431(3) 0.60896(8) 0.0302(5) Uani 1 1 d . . .
O16 O -0.2975(2) 1.0675(3) 0.49209(8) 0.0287(5) Uani 1 1 d . A .
H16 H -0.3194 1.0878 0.4644 0.043 Uiso 1 1 calc R . .
O17 O -0.4363(2) 0.8861(2) 0.27483(8) 0.0278(5) Uani 1 1 d . . .
O18 O -0.1149(2) 1.1523(3) 0.24298(9) 0.0310(5) Uani 1 1 d . . .
O19 O -0.0246(3) 1.4164(3) 0.30359(8) 0.0326(6) Uani 1 1 d . . .
H19A H -0.0981 1.3854 0.3078 0.039 Uiso 1 1 d R . .
H19B H -0.0041 1.4982 0.3145 0.039 Uiso 1 1 d R . .
O20 O -0.3657(3) 0.7996(3) 0.15825(8) 0.0326(6) Uani 1 1 d . . .
H20A H -0.2872 0.7726 0.1647 0.039 Uiso 1 1 d R . .
H20B H -0.3740 0.8331 0.1317 0.039 Uiso 1 1 d R . .
O21 O 0.2507(3) 1.1669(3) 0.22487(11) 0.0497(8) Uani 1 1 d . . .
H21A H 0.3085 1.2302 0.2243 0.060 Uiso 1 1 d R . .
H21B H 0.1943 1.1918 0.2026 0.060 Uiso 1 1 d R . .
N1 N -0.1612(3) 1.0260(3) 0.09909(9) 0.0254(6) Uani 1 1 d . . .
N2 N 0.1719(3) 1.4142(3) 0.11334(9) 0.0254(6) Uani 1 1 d . . .
N3 N -0.0417(3) 1.2621(3) -0.03624(10) 0.0265(6) Uani 1 1 d . . .
N4 N -0.4825(3) 1.2864(3) 0.45210(9) 0.0231(5) Uani 1 1 d . . .
N5 N -0.6060(3) 1.3634(3) 0.60012(10) 0.0285(6) Uani 1 1 d . . .
N6 N -0.2666(3) 1.0006(3) 0.58180(9) 0.0227(5) Uani 1 1 d . . .
N7 N -0.4500(3) 1.0975(3) 0.33281(9) 0.0242(6) Uani 1 1 d . . .
H7A H -0.3666 1.1149 0.3446 0.029 Uiso 1 1 d R . .
H7B H -0.5035 1.1699 0.3367 0.029 Uiso 1 1 d R . .
H7C H -0.4773 1.0073 0.3348 0.029 Uiso 1 1 d R . .
N8 N -0.4266(3) 1.1262(3) 0.28811(9) 0.0248(6) Uani 1 1 d . . .
H8A H -0.3844 1.2063 0.2900 0.030 Uiso 1 1 d R . .
N9 N -0.3625(3) 1.0335(3) 0.22374(10) 0.0300(6) Uani 1 1 d . . .
H9 H -0.3479 0.9589 0.2082 0.036 Uiso 1 1 d R . .
N10 N -0.3332(3) 1.1716(3) 0.21186(9) 0.0251(6) Uani 1 1 d . . .
H10 H -0.3943 1.2281 0.1991 0.030 Uiso 1 1 d R . .
N11 N -0.1940(3) 1.3554(3) 0.20401(9) 0.0234(5) Uani 1 1 d . . .
H11 H -0.2374 1.3680 0.1771 0.028 Uiso 1 1 d R . .
N12 N -0.0630(3) 1.4065(3) 0.20819(9) 0.0249(6) Uani 1 1 d . . .
H12A H -0.0562 1.5008 0.2039 0.030 Uiso 1 1 d R . .
H12B H -0.0123 1.3533 0.1932 0.030 Uiso 1 1 d R . .
H12C H -0.0309 1.4146 0.2377 0.030 Uiso 1 1 d R . .
C1 C -0.0786(3) 1.1270(3) 0.07867(11) 0.0226(6) Uani 1 1 d . . .
C2 C 0.0109(3) 1.2115(3) 0.10997(11) 0.0228(6) Uani 1 1 d . . .
C3 C 0.0834(3) 1.3139(3) 0.08675(11) 0.0221(6) Uani 1 1 d . . .
C4 C 0.0687(3) 1.3244(3) 0.03992(11) 0.0227(6) Uani 1 1 d . . .
H4 H 0.1204 1.3917 0.0266 0.027 Uiso 1 1 calc R . .
C5 C -0.0203(3) 1.2384(3) 0.01209(11) 0.0223(6) Uani 1 1 d . . .
C6 C -0.0971(3) 1.1355(3) 0.03178(11) 0.0235(6) Uani 1 1 d . . .
C7 C -0.4674(3) 1.2450(3) 0.49877(10) 0.0216(6) Uani 1 1 d . A .
C8 C -0.5435(3) 1.3140(3) 0.52710(10) 0.0211(6) Uani 1 1 d . . .
H8 H -0.6063 1.3840 0.5147 0.025 Uiso 1 1 calc R A .
C9 C -0.5284(3) 1.2818(3) 0.57266(10) 0.0216(6) Uani 1 1 d . A .
C10 C -0.4362(3) 1.1739(3) 0.59402(10) 0.0207(6) Uani 1 1 d . . .
C11 C -0.3638(3) 1.1089(3) 0.56242(10) 0.0211(6) Uani 1 1 d . A .
C12 C -0.3751(3) 1.1382(3) 0.51652(10) 0.0208(6) Uani 1 1 d . . .
C13 C -0.4084(3) 1.0078(3) 0.26288(10) 0.0220(6) Uani 1 1 d . . .
C14 C -0.2059(3) 1.2176(3) 0.22059(10) 0.0235(6) Uani 1 1 d . . .
O12A O -0.609(4) 1.322(4) 0.6393(7) 0.043(5) Uani 0.32(5) 1 d PU A 2
O22 O -0.2899(4) 1.3961(4) 0.31640(16) 0.0744(13) Uani 1 1 d U B 1
H22A H -0.2469 1.3512 0.3384 0.089 Uiso 1 1 d R B 1
H22B H -0.3560 1.4318 0.3253 0.089 Uiso 1 1 d R B 1
O23 O 0.1519(4) 1.1832(5) 0.30417(16) 0.0291(13) Uani 0.538(7) 1 d PU C 1
H23A H 0.1587 1.1843 0.2764 0.035 Uiso 0.538(7) 1 d PR C 1
H23B H 0.1015 1.2546 0.3027 0.035 Uiso 0.538(7) 1 d PR C 1
O24 O 0.1022(6) 1.1780(6) 0.33294(19) 0.0332(16) Uani 0.462(7) 1 d PU C 2
H24A H 0.0627 1.2452 0.3175 0.040 Uiso 0.462(7) 1 d PR C 2
H24B H 0.0823 1.1948 0.3587 0.040 Uiso 0.462(7) 1 d PR C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.232(4) . ?
O2 N1 1.222(4) . ?
O3 C2 1.262(4) . ?
O4 N2 1.233(4) . ?
O5 N2 1.239(4) . ?
O6 N3 1.225(4) . ?
O7 N3 1.255(4) . ?
O8 C6 1.342(4) . ?
O8 H8B 0.8400 . ?
O9 N4 1.252(3) . ?
O10 N4 1.234(4) . ?
O11 N5 1.224(4) . ?
O12 N5 1.244(9) . ?
O13 C10 1.263(4) . ?
O14 N6 1.216(4) . ?
O15 N6 1.226(3) . ?
O16 C12 1.338(4) . ?
O16 H16 0.8400 . ?
O17 C13 1.233(4) . ?
O18 C14 1.221(4) . ?
O19 H19A 0.8399 . ?
O19 H19B 0.8399 . ?
O20 H20A 0.8399 . ?
O20 H20B 0.8404 . ?
O21 H21A 0.8399 . ?
O21 H21B 0.8399 . ?
N1 C1 1.465(4) . ?
N2 C3 1.447(4) . ?
N3 C5 1.435(4) . ?
N4 C7 1.424(4) . ?
N5 O12A 1.232(16) . ?
N5 C9 1.448(4) . ?
N6 C11 1.471(4) . ?
N7 N8 1.414(4) . ?
N7 H7A 0.8897 . ?
N7 H7B 0.8900 . ?
N7 H7C 0.8901 . ?
N8 C13 1.362(4) . ?
N8 H8A 0.8598 . ?
N9 C13 1.348(4) . ?
N9 N10 1.378(4) . ?
N9 H9 0.8601 . ?
N10 C14 1.366(4) . ?
N10 H10 0.8602 . ?
N11 C14 1.385(4) . ?
N11 N12 1.421(4) . ?
N11 H11 0.8599 . ?
N12 H12A 0.8898 . ?
N12 H12B 0.8900 . ?
N12 H12C 0.8899 . ?
C1 C6 1.379(5) . ?
C1 C2 1.434(4) . ?
C2 C3 1.453(4) . ?
C3 C4 1.380(4) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.428(4) . ?
C7 C8 1.398(4) . ?
C7 C12 1.417(4) . ?
C8 C9 1.371(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.456(4) . ?
C10 C11 1.427(4) . ?
C11 C12 1.378(4) . ?
O22 H22A 0.8401 . ?
O22 H22B 0.8399 . ?
O23 H23A 0.8400 . ?
O23 H23B 0.8400 . ?
O23 H24A 1.2065 . ?
O24 H23B 1.1467 . ?
O24 H24A 0.8401 . ?
O24 H24B 0.8397 . ?

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
C6 O8 H8B 109.5 . . ?
C12 O16 H16 109.5 . . ?
H19A O19 H19B 115.5 . . ?
H20A O20 H20B 105.7 . . ?
H21A O21 H21B 101.2 . . ?
O2 N1 O1 124.1(3) . . ?
O2 N1 C1 118.5(3) . . ?
O1 N1 C1 117.4(3) . . ?
O4 N2 O5 121.8(3) . . ?
O4 N2 C3 120.5(3) . . ?
O5 N2 C3 117.7(3) . . ?
O6 N3 O7 121.7(3) . . ?
O6 N3 C5 119.7(3) . . ?
O7 N3 C5 118.6(3) . . ?
O10 N4 O9 121.3(3) . . ?
O10 N4 C7 119.9(3) . . ?
O9 N4 C7 118.8(3) . . ?
O11 N5 O12A 118.5(10) . . ?
O11 N5 O12 120.1(5) . . ?
O12A N5 O12 30.3(12) . . ?
O11 N5 C9 119.4(3) . . ?
O12A N5 C9 118.3(8) . . ?
O12 N5 C9 119.3(4) . . ?
O14 N6 O15 124.7(3) . . ?
O14 N6 C11 118.2(3) . . ?
O15 N6 C11 117.1(3) . . ?
N8 N7 H7A 91.9 . . ?
N8 N7 H7B 100.6 . . ?
H7A N7 H7B 113.2 . . ?
N8 N7 H7C 110.2 . . ?
H7A N7 H7C 116.2 . . ?
H7B N7 H7C 119.5 . . ?
C13 N8 N7 115.2(3) . . ?
C13 N8 H8A 128.5 . . ?
N7 N8 H8A 105.3 . . ?
C13 N9 N10 120.6(3) . . ?
C13 N9 H9 116.1 . . ?
N10 N9 H9 123.2 . . ?
C14 N10 N9 119.2(3) . . ?
C14 N10 H10 120.4 . . ?
N9 N10 H10 120.4 . . ?
C14 N11 N12 114.6(3) . . ?
C14 N11 H11 113.2 . . ?
N12 N11 H11 112.3 . . ?
N11 N12 H12A 114.4 . . ?
N11 N12 H12B 113.5 . . ?
H12A N12 H12B 114.2 . . ?
N11 N12 H12C 108.1 . . ?
H12A N12 H12C 91.9 . . ?
H12B N12 H12C 112.7 . . ?
C6 C1 C2 126.4(3) . . ?
C6 C1 N1 117.5(3) . . ?
C2 C1 N1 116.0(3) . . ?
O3 C2 C1 122.2(3) . . ?
O3 C2 C3 125.6(3) . . ?
C1 C2 C3 112.2(3) . . ?
C4 C3 N2 117.5(3) . . ?
C4 C3 C2 123.1(3) . . ?
N2 C3 C2 119.4(3) . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 N3 119.3(3) . . ?
C6 C5 N3 120.6(3) . . ?
O8 C6 C1 119.2(3) . . ?
O8 C6 C5 123.5(3) . . ?
C1 C6 C5 117.3(3) . . ?
C8 C7 C12 120.4(3) . . ?
C8 C7 N4 118.7(3) . . ?
C12 C7 N4 120.8(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 N5 117.3(3) . . ?
C8 C9 C10 122.8(3) . . ?
N5 C9 C10 119.8(3) . . ?
O13 C10 C11 121.1(3) . . ?
O13 C10 C9 126.5(3) . . ?
C11 C10 C9 112.3(3) . . ?
C12 C11 C10 126.8(3) . . ?
C12 C11 N6 117.8(3) . . ?
C10 C11 N6 115.4(3) . . ?
O16 C12 C11 118.6(3) . . ?
O16 C12 C7 124.6(3) . . ?
C11 C12 C7 116.8(3) . . ?
O17 C13 N9 122.9(3) . . ?
O17 C13 N8 121.5(3) . . ?
N9 C13 N8 115.6(3) . . ?
O18 C14 N10 125.4(3) . . ?
O18 C14 N11 123.3(3) . . ?
N10 C14 N11 111.1(3) . . ?
H22A O22 H22B 107.6 . . ?
H23A O23 H23B 95.0 . . ?
H23A O23 H24A 120.4 . . ?
H23B O23 H24A 30.8 . . ?
H23B O24 H24A 33.8 . . ?
H23B O24 H24B 129.1 . . ?
H24A O24 H24B 101.1 . . ?

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
C13 N9 N10 C14 98.1(4) . . . . ?
O2 N1 C1 C6 64.4(4) . . . . ?
O1 N1 C1 C6 -115.9(3) . . . . ?
O2 N1 C1 C2 -117.7(3) . . . . ?
O1 N1 C1 C2 62.0(4) . . . . ?
C6 C1 C2 O3 -177.1(3) . . . . ?
N1 C1 C2 O3 5.3(4) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
N1 C1 C2 C3 -176.8(3) . . . . ?
O4 N2 C3 C4 157.8(3) . . . . ?
O5 N2 C3 C4 -21.3(4) . . . . ?
O4 N2 C3 C2 -19.8(5) . . . . ?
O5 N2 C3 C2 161.0(3) . . . . ?
O3 C2 C3 C4 176.3(3) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
O3 C2 C3 N2 -6.2(5) . . . . ?
C1 C2 C3 N2 176.0(3) . . . . ?
N2 C3 C4 C5 -175.9(3) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C3 C4 C5 N3 174.1(3) . . . . ?
O6 N3 C5 C4 -3.2(4) . . . . ?
O7 N3 C5 C4 177.9(3) . . . . ?
O6 N3 C5 C6 171.8(3) . . . . ?
O7 N3 C5 C6 -7.2(4) . . . . ?
C2 C1 C6 O8 -178.6(3) . . . . ?
N1 C1 C6 O8 -1.0(4) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
N1 C1 C6 C5 177.4(3) . . . . ?
C4 C5 C6 O8 178.5(3) . . . . ?
N3 C5 C6 O8 3.6(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
N3 C5 C6 C1 -174.7(3) . . . . ?
O10 N4 C7 C8 5.2(4) . . . . ?
O9 N4 C7 C8 -174.7(3) . . . . ?
O10 N4 C7 C12 -173.5(3) . . . . ?
O9 N4 C7 C12 6.6(4) . . . . ?
C12 C7 C8 C9 1.3(5) . . . . ?
N4 C7 C8 C9 -177.3(3) . . . . ?
C7 C8 C9 N5 176.9(3) . . . . ?
C7 C8 C9 C10 -1.3(5) . . . . ?
O11 N5 C9 C8 11.3(5) . . . . ?
O12A N5 C9 C8 169(3) . . . . ?
O12 N5 C9 C8 -156.0(15) . . . . ?
O11 N5 C9 C10 -170.5(3) . . . . ?
O12A N5 C9 C10 -13(3) . . . . ?
O12 N5 C9 C10 22.2(15) . . . . ?
C8 C9 C10 O13 -176.9(3) . . . . ?
N5 C9 C10 O13 5.0(5) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
N5 C9 C10 C11 -177.2(3) . . . . ?
O13 C10 C11 C12 177.3(3) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
O13 C10 C11 N6 -3.3(4) . . . . ?
C9 C10 C11 N6 178.8(3) . . . . ?
O14 N6 C11 C12 -68.6(4) . . . . ?
O15 N6 C11 C12 112.9(3) . . . . ?
O14 N6 C11 C10 111.9(3) . . . . ?
O15 N6 C11 C10 -66.5(4) . . . . ?
C10 C11 C12 O16 179.2(3) . . . . ?
N6 C11 C12 O16 -0.2(4) . . . . ?
C10 C11 C12 C7 0.7(5) . . . . ?
N6 C11 C12 C7 -178.7(3) . . . . ?
C8 C7 C12 O16 -179.4(3) . . . . ?
N4 C7 C12 O16 -0.7(5) . . . . ?
C8 C7 C12 C11 -1.0(4) . . . . ?
N4 C7 C12 C11 177.6(3) . . . . ?
N10 N9 C13 O17 179.7(3) . . . . ?
N10 N9 C13 N8 1.9(5) . . . . ?
N7 N8 C13 O17 13.9(5) . . . . ?
N7 N8 C13 N9 -168.2(3) . . . . ?
N9 N10 C14 O18 -8.8(5) . . . . ?
N9 N10 C14 N11 176.5(3) . . . . ?
N12 N11 C14 O18 10.3(4) . . . . ?
N12 N11 C14 N10 -174.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8B O7 0.84 1.84 2.558(4) 143.0 .
O8 H8B O11 0.84 2.31 2.901(4) 127.3 2_445
O8 H8B N3 0.84 2.46 2.900(4) 113.5 .
O16 H16 O9 0.84 1.87 2.577(3) 141.4 .
O16 H16 O5 0.84 2.24 2.819(3) 126.5 2_545
O16 H16 N4 0.84 2.48 2.909(4) 112.2 .
O19 H19A O22 0.84 2.04 2.833(5) 157.1 .
O19 H19B O3 0.84 2.08 2.879(3) 157.9 2
O20 H20A O23 0.84 1.75 2.547(5) 156.4 2_545
O20 H20A O24 0.84 2.09 2.918(7) 167.0 2_545
O20 H20B O10 0.84 2.15 2.969(3) 164.4 2_445
O21 H21A O17 0.84 1.96 2.796(4) 176.1 2
O21 H21B O3 0.84 2.10 2.911(4) 161.5 .
N7 H7A O5 0.89 2.38 2.932(4) 120.6 2_545
N7 H7A O4 0.89 2.66 3.284(4) 128.1 2_545
N7 H7B O20 0.89 1.83 2.717(4) 171.2 2_455
N7 H7C O13 0.89 1.99 2.783(4) 148.4 3_476
N8 H8A O22 0.86 2.10 2.934(4) 161.7 .
N9 H9 O20 0.86 2.08 2.915(4) 162.4 .
N10 H10 O13 0.86 2.27 2.934(4) 133.9 4_585
N10 H10 O12 0.86 2.45 2.954(10) 117.9 4_585
N10 H10 O17 0.86 2.50 3.178(4) 136.1 2_455
N10 H10 O12A 0.86 2.65 3.28(4) 131.4 4_585
N11 H11 O13 0.86 2.09 2.849(4) 146.9 4_585
N11 H11 O15 0.86 2.38 3.023(4) 131.5 4_585
N12 H12A O23 0.89 1.96 2.735(5) 145.1 2
N12 H12A O24 0.89 1.99 2.804(6) 151.1 2
N12 H12A O18 0.89 2.59 3.136(4) 120.7 2
N12 H12B O3 0.89 2.00 2.832(4) 154.9 .
N12 H12B O4 0.89 2.45 3.059(4) 126.4 .
N12 H12C O19 0.89 1.95 2.801(4) 159.8 .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.136
