# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1406844'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-04-18 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 O10'
_chemical_formula_weight         393.26

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   P21/c

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

_cell_length_a                   15.483(3)
_cell_length_b                   5.4173(10)
_cell_length_c                   19.632(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.484(12)
_cell_angle_gamma                90.00
_cell_volume                     1498.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    244
_cell_measurement_theta_min      1.45
_cell_measurement_theta_max      29.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12773
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         29.47
_reflns_number_total             4102
_reflns_number_gt                2126
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0586P)²+0.3988P] 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         4102
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1514
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.49562(15) 0.9046(4) 0.12441(13) 0.0403(5) Uani 1 1 d . . .
C2 C 0.4335(2) 0.6044(5) 0.16277(17) 0.0629(8) Uani 1 1 d . . .
H1 H 0.3886 0.4954 0.1655 0.075 Uiso 1 1 calc R . .
C3 C 0.18464(14) 0.5277(4) 0.20664(12) 0.0367(5) Uani 1 1 d . . .
C4 C 0.12547(15) 0.7001(4) 0.22125(11) 0.0356(5) Uani 1 1 d . . .
C5 C 0.03165(15) 0.7385(4) 0.17798(12) 0.0364(5) Uani 1 1 d . . .
C6 C -0.01407(14) 0.5820(4) 0.11408(12) 0.0359(5) Uani 1 1 d . . .
C7 C 0.03845(15) 0.3908(4) 0.09861(12) 0.0367(5) Uani 1 1 d . . .
C8 C 0.13585(15) 0.3685(4) 0.14303(12) 0.0358(5) Uani 1 1 d . . .
N1 N 0.59409(14) 1.2064(4) 0.10301(12) 0.0555(6) Uani 1 1 d . . .
H3 H 0.6344 1.0815 0.0925 0.067 Uiso 1 1 d R . .
H4 H 0.6138 1.2613 0.1526 0.067 Uiso 1 1 d R . .
N2 N 0.50488(13) 1.0955(4) 0.08578(11) 0.0497(5) Uani 1 1 d . . .
H5 H 0.4517 1.1555 0.0452 0.060 Uiso 1 1 d R . .
N3 N 0.56066(14) 0.7933(4) 0.18360(11) 0.0470(5) Uani 1 1 d . . .
H2 H 0.6245 0.8521 0.2116 0.056 Uiso 1 1 d R . .
N4 N 0.52180(17) 0.6031(4) 0.20864(13) 0.0629(7) Uani 1 1 d . . .
N5 N 0.41335(13) 0.7854(4) 0.10940(12) 0.0477(5) Uani 1 1 d . . .
N6 N 0.32927(14) 0.8475(4) 0.04792(13) 0.0599(6) Uani 1 1 d . . .
H7 H 0.3018 0.7004 0.0243 0.072 Uiso 1 1 d R . .
H6 H 0.2932 0.9210 0.0649 0.072 Uiso 1 1 d R . .
N7 N -0.10944(13) 0.6190(4) 0.06773(11) 0.0435(5) Uani 1 1 d . . .
N8 N 0.18973(14) 0.1817(4) 0.12558(11) 0.0423(5) Uani 1 1 d . . .
N9 N 0.17188(14) 0.8465(4) 0.28908(11) 0.0423(5) Uani 1 1 d . . .
O1 O 0.2074(2) 1.0406(4) 0.28548(12) 0.1047(10) Uani 1 1 d . . .
O2 O 0.17876(16) 0.7597(4) 0.34790(10) 0.0703(6) Uani 1 1 d . . .
O3 O -0.01283(12) 0.9186(3) 0.19730(9) 0.0521(5) Uani 1 1 d . . .
H8 H -0.0795 0.9204 0.1536 0.078 Uiso 1 1 d R . .
O4 O -0.15516(12) 0.7914(4) 0.08003(10) 0.0607(5) Uani 1 1 d . . .
O5 O -0.15169(12) 0.4811(4) 0.01236(10) 0.0567(5) Uani 1 1 d . . .
O6 O -0.00300(12) 0.2393(3) 0.04129(9) 0.0516(5) Uani 1 1 d . . .
H9 H -0.0640 0.2888 0.0241 0.077 Uiso 1 1 d R . .
O7 O 0.15064(14) -0.0041(3) 0.09131(12) 0.0656(6) Uani 1 1 d . . .
O8 O 0.27459(13) 0.2107(4) 0.14545(14) 0.0817(7) Uani 1 1 d . . .
O9 O 0.27174(10) 0.5209(3) 0.24791(9) 0.0498(5) Uani 1 1 d . . .
O10 O 0.36542(13) 0.1541(4) 0.46485(12) 0.0753(7) Uani 1 1 d . . .
H10 H 0.3003 0.1796 0.4505 0.113 Uiso 1 1 d R . .
H11 H 0.3565 0.0176 0.4322 0.113 Uiso 1 1 d R . .


_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 N2 1.325(3) . ?
C1 N3 1.326(3) . ?
C1 N5 1.347(3) . ?
C2 N4 1.288(3) . ?
C2 N5 1.373(4) . ?
C2 H1 0.9300 . ?
C3 O9 1.253(2) . ?
C3 C4 1.418(3) . ?
C3 C8 1.447(3) . ?
C4 C5 1.361(3) . ?
C4 N9 1.458(3) . ?
C5 O3 1.337(3) . ?
C5 C6 1.435(3) . ?
C6 N7 1.391(3) . ?
C6 C7 1.425(3) . ?
C7 O6 1.324(2) . ?
C7 C8 1.400(3) . ?
C8 N8 1.440(3) . ?
N1 N2 1.413(3) . ?
N1 H3 0.9982 . ?
N1 H4 0.9400 . ?
N2 H5 0.9349 . ?
N3 N4 1.382(3) . ?
N3 H2 0.9647 . ?
N5 N6 1.401(3) . ?
N6 H7 0.9308 . ?
N6 H6 0.8579 . ?
N7 O4 1.255(3) . ?
N7 O5 1.256(2) . ?
N8 O8 1.216(3) . ?
N8 O7 1.223(2) . ?
N9 O1 1.203(3) . ?
N9 O2 1.210(3) . ?
O3 H8 1.0332 . ?
O6 H9 0.9026 . ?
O10 H10 0.9379 . ?
O10 H11 0.9502 . ?

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 C1 N3 129.3(2) . . ?
N2 C1 N5 124.4(2) . . ?
N3 C1 N5 106.2(2) . . ?
N4 C2 N5 112.1(2) . . ?
N4 C2 H1 123.9 . . ?
N5 C2 H1 123.9 . . ?
O9 C3 C4 120.06(19) . . ?
O9 C3 C8 125.3(2) . . ?
C4 C3 C8 114.66(18) . . ?
C5 C4 C3 125.89(19) . . ?
C5 C4 N9 118.8(2) . . ?
C3 C4 N9 115.32(18) . . ?
O3 C5 C4 118.5(2) . . ?
O3 C5 C6 123.66(19) . . ?
C4 C5 C6 117.9(2) . . ?
N7 C6 C7 120.66(19) . . ?
N7 C6 C5 119.5(2) . . ?
C7 C6 C5 119.85(19) . . ?
O6 C7 C8 119.6(2) . . ?
O6 C7 C6 120.88(19) . . ?
C8 C7 C6 119.51(19) . . ?
C7 C8 N8 119.55(19) . . ?
C7 C8 C3 121.9(2) . . ?
N8 C8 C3 118.53(18) . . ?
N2 N1 H3 107.2 . . ?
N2 N1 H4 104.4 . . ?
H3 N1 H4 117.8 . . ?
C1 N2 N1 121.46(19) . . ?
C1 N2 H5 119.6 . . ?
N1 N2 H5 119.0 . . ?
C1 N3 N4 111.48(19) . . ?
C1 N3 H2 125.2 . . ?
N4 N3 H2 122.5 . . ?
C2 N4 N3 103.9(2) . . ?
C1 N5 C2 106.3(2) . . ?
C1 N5 N6 122.0(2) . . ?
C2 N5 N6 131.7(2) . . ?
N5 N6 H7 107.0 . . ?
N5 N6 H6 107.4 . . ?
H7 N6 H6 110.8 . . ?
O4 N7 O5 118.44(19) . . ?
O4 N7 C6 120.80(19) . . ?
O5 N7 C6 120.8(2) . . ?
O8 N8 O7 120.4(2) . . ?
O8 N8 C8 119.22(19) . . ?
O7 N8 C8 120.40(19) . . ?
O1 N9 O2 122.3(2) . . ?
O1 N9 C4 119.1(2) . . ?
O2 N9 C4 118.4(2) . . ?
C5 O3 H8 103.0 . . ?
C7 O6 H9 101.4 . . ?
H10 O10 H11 94.2 . . ?

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
O9 C3 C4 C5 175.0(2) . . . . ?
C8 C3 C4 C5 -5.6(3) . . . . ?
O9 C3 C4 N9 -4.8(3) . . . . ?
C8 C3 C4 N9 174.63(19) . . . . ?
C3 C4 C5 O3 -176.1(2) . . . . ?
N9 C4 C5 O3 3.7(3) . . . . ?
C3 C4 C5 C6 4.1(3) . . . . ?
N9 C4 C5 C6 -176.13(19) . . . . ?
O3 C5 C6 N7 1.5(3) . . . . ?
C4 C5 C6 N7 -178.7(2) . . . . ?
O3 C5 C6 C7 -178.6(2) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
N7 C6 C7 O6 -2.2(3) . . . . ?
C5 C6 C7 O6 177.9(2) . . . . ?
N7 C6 C7 C8 175.5(2) . . . . ?
C5 C6 C7 C8 -4.4(3) . . . . ?
O6 C7 C8 N8 0.3(3) . . . . ?
C6 C7 C8 N8 -177.5(2) . . . . ?
O6 C7 C8 C3 -179.5(2) . . . . ?
C6 C7 C8 C3 2.7(3) . . . . ?
O9 C3 C8 C7 -178.7(2) . . . . ?
C4 C3 C8 C7 2.0(3) . . . . ?
O9 C3 C8 N8 1.5(3) . . . . ?
C4 C3 C8 N8 -177.83(19) . . . . ?
N3 C1 N2 N1 2.8(4) . . . . ?
N5 C1 N2 N1 -177.7(2) . . . . ?
N2 C1 N3 N4 178.7(2) . . . . ?
N5 C1 N3 N4 -0.8(3) . . . . ?
N5 C2 N4 N3 0.1(3) . . . . ?
C1 N3 N4 C2 0.5(3) . . . . ?
N2 C1 N5 C2 -178.7(2) . . . . ?
N3 C1 N5 C2 0.8(3) . . . . ?
N2 C1 N5 N6 3.1(4) . . . . ?
N3 C1 N5 N6 -177.3(2) . . . . ?
N4 C2 N5 C1 -0.6(3) . . . . ?
N4 C2 N5 N6 177.3(3) . . . . ?
C7 C6 N7 O4 -178.0(2) . . . . ?
C5 C6 N7 O4 1.9(3) . . . . ?
C7 C6 N7 O5 1.7(3) . . . . ?
C5 C6 N7 O5 -178.4(2) . . . . ?
C7 C8 N8 O8 155.3(2) . . . . ?
C3 C8 N8 O8 -24.9(3) . . . . ?
C7 C8 N8 O7 -24.8(3) . . . . ?
C3 C8 N8 O7 155.0(2) . . . . ?
C5 C4 N9 O1 -89.4(3) . . . . ?
C3 C4 N9 O1 90.4(3) . . . . ?
C5 C4 N9 O2 95.6(3) . . . . ?
C3 C4 N9 O2 -84.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        29.47
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_bn1886
_database_code_depnum_ccdc_archive 'CCDC 1406850'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-04-18 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 H14 N12 O15'
_chemical_formula_weight         590.37

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.0048(18)
_cell_length_b                   11.527(2)
_cell_length_c                   13.178(2)
_cell_angle_alpha                69.469(9)
_cell_angle_beta                 73.214(9)
_cell_angle_gamma                80.053(10)
_cell_volume                     1086.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4439
_cell_measurement_theta_min      2.666
_cell_measurement_theta_max      31.507

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.164
_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            15158
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         31.50
_reflns_number_total             6993
_reflns_number_gt                5108
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0695P)²+2.6600P] 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         6993
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.2111
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.0406(2) 0.19300(15) 0.46234(15) 0.0158(4) Uani 1 1 d . . .
O2 O 0.3947(3) 0.16199(16) 0.46241(18) 0.0211(4) Uani 1 1 d . . .
O3 O 0.4140(3) 0.28047(19) 0.55370(19) 0.0260(5) Uani 1 1 d . . .
O4 O 0.3018(3) 0.71518(18) 0.3443(2) 0.0283(5) Uani 1 1 d . . .
O5 O 0.0705(3) 0.77043(17) 0.2794(2) 0.0264(5) Uani 1 1 d . . .
O6 O -0.3281(3) 0.46371(19) 0.36793(19) 0.0254(4) Uani 1 1 d . . .
O7 O -0.2144(3) 0.28646(18) 0.3476(2) 0.0290(5) Uani 1 1 d . . .
O8 O 0.4801(3) 0.82877(16) 0.03421(16) 0.0193(4) Uani 1 1 d . . .
O9 O 0.1539(3) 0.87946(19) -0.0014(2) 0.0336(5) Uani 1 1 d . . .
O10 O 0.0945(3) 0.7421(2) -0.0599(2) 0.0342(5) Uani 1 1 d . . .
O11 O 0.1921(3) 0.31536(19) 0.1478(2) 0.0293(5) Uani 1 1 d . . .
O12 O 0.4311(3) 0.25361(18) 0.2040(2) 0.0282(5) Uani 1 1 d . . .
O13 O 0.8367(3) 0.55164(19) 0.12729(19) 0.0262(4) Uani 1 1 d . . .
O14 O 0.7258(3) 0.7277(2) 0.1520(2) 0.0332(5) Uani 1 1 d . . .
O15 O 0.7062(3) 0.08047(19) 0.28609(17) 0.0207(4) Uani 1 1 d . . .
N1 N 0.0834(3) 0.02079(18) 0.32338(17) 0.0150(4) Uani 1 1 d . . .
N2 N 0.0682(3) 0.05281(19) 0.21592(18) 0.0157(4) Uani 1 1 d . . .
N3 N 0.3370(3) -0.00520(18) 0.20671(17) 0.0141(4) Uani 1 1 d . . .
N4 N 0.5202(3) -0.0287(2) 0.17316(19) 0.0153(4) Uani 1 1 d . . .
N5 N 0.3372(3) -0.04709(18) 0.39752(17) 0.0130(4) Uani 1 1 d . . .
N6 N 0.2212(3) -0.04141(18) 0.50185(17) 0.0131(4) Uani 1 1 d . . .
N7 N 0.3507(3) 0.25717(18) 0.48890(18) 0.0155(4) Uani 1 1 d . . .
N8 N 0.1730(3) 0.69128(18) 0.32512(18) 0.0169(4) Uani 1 1 d . . .
N9 N -0.2041(3) 0.38354(19) 0.36368(19) 0.0167(4) Uani 1 1 d . . .
N10 N 0.1721(3) 0.7735(2) -0.0063(2) 0.0201(4) Uani 1 1 d . . .
N11 N 0.3265(3) 0.33663(19) 0.16376(18) 0.0164(4) Uani 1 1 d . . .
N12 N 0.7155(3) 0.6333(2) 0.1325(2) 0.0189(4) Uani 1 1 d . . .
C1 C 0.2493(3) -0.0136(2) 0.31441(19) 0.0117(4) Uani 1 1 d . . .
C2 C 0.2172(4) 0.0371(2) 0.1462(2) 0.0178(5) Uani 1 1 d . . .
H2 H 0.2368 0.0525 0.0681 0.021 Uiso 1 1 calc R . .
C3 C 0.0742(3) 0.3057(2) 0.42593(19) 0.0111(4) Uani 1 1 d . . .
C4 C 0.2241(3) 0.3483(2) 0.4385(2) 0.0130(4) Uani 1 1 d . . .
C5 C 0.2552(3) 0.4712(2) 0.4089(2) 0.0133(4) Uani 1 1 d . . .
H5 H 0.3544 0.4935 0.4217 0.016 Uiso 1 1 calc R . .
C6 C 0.1376(3) 0.5615(2) 0.3601(2) 0.0130(4) Uani 1 1 d . . .
C7 C -0.0112(3) 0.5315(2) 0.3442(2) 0.0134(4) Uani 1 1 d . . .
H7 H -0.0912 0.5949 0.3119 0.016 Uiso 1 1 calc R . .
C8 C -0.0410(3) 0.4080(2) 0.3762(2) 0.0125(4) Uani 1 1 d . . .
C9 C 0.4399(3) 0.7186(2) 0.0668(2) 0.0139(4) Uani 1 1 d . . .
C10 C 0.2897(3) 0.6800(2) 0.0514(2) 0.0152(4) Uani 1 1 d . . .
C11 C 0.2525(3) 0.5584(2) 0.0816(2) 0.0155(4) Uani 1 1 d . . .
H11 H 0.1518 0.5391 0.0681 0.019 Uiso 1 1 calc R . .
C12 C 0.3647(3) 0.4644(2) 0.1321(2) 0.0144(4) Uani 1 1 d . . .
C13 C 0.5153(3) 0.4906(2) 0.1484(2) 0.0142(4) Uani 1 1 d . . .
H13 H 0.5934 0.4251 0.1803 0.017 Uiso 1 1 calc R . .
C14 C 0.5510(3) 0.6126(2) 0.1180(2) 0.0142(4) Uani 1 1 d . . .
H2N H -0.018(5) 0.081(3) 0.201(3) 0.012(8) Uiso 1 1 d . . .
H4A H 0.554(4) 0.027(3) 0.112(3) 0.009(7) Uiso 1 1 d . . .
H4B H 0.539(4) -0.099(3) 0.160(3) 0.010(7) Uiso 1 1 d . . .
H5N H 0.402(5) -0.113(3) 0.403(3) 0.018(8) Uiso 1 1 d . . .
H6A H 0.143(4) -0.095(3) 0.522(2) 0.006(6) Uiso 1 1 d . . .
H6B H 0.291(5) -0.061(3) 0.564(3) 0.022(9) Uiso 1 1 d . . .
H6C H 0.160(5) 0.037(3) 0.492(3) 0.019(8) Uiso 1 1 d . . .
H15A H 0.653(5) 0.035(3) 0.274(3) 0.021(9) Uiso 1 1 d . . .
H15B H 0.657(6) 0.145(4) 0.275(4) 0.041(12) 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 C3 1.265(3) . ?
O2 N7 1.230(3) . ?
O3 N7 1.231(3) . ?
O4 N8 1.225(3) . ?
O5 N8 1.228(3) . ?
O6 N9 1.237(3) . ?
O7 N9 1.230(3) . ?
O8 C9 1.256(3) . ?
O9 N10 1.227(3) . ?
O10 N10 1.235(3) . ?
O11 N11 1.233(3) . ?
O12 N11 1.234(3) . ?
O13 N12 1.234(3) . ?
O14 N12 1.223(3) . ?
O15 H15A 0.81(4) . ?
O15 H15B 0.77(5) . ?
N1 C1 1.302(3) . ?
N1 N2 1.369(3) . ?
N2 C2 1.307(4) . ?
N2 H2N 0.75(3) . ?
N3 C2 1.342(4) . ?
N3 C1 1.367(3) . ?
N3 N4 1.411(3) . ?
N4 H4A 0.85(3) . ?
N4 H4B 0.86(3) . ?
N5 C1 1.378(3) . ?
N5 N6 1.436(3) . ?
N5 H5N 0.83(3) . ?
N6 H6A 0.88(3) . ?
N6 H6B 1.06(4) . ?
N6 H6C 0.93(3) . ?
N7 C4 1.450(3) . ?
N8 C6 1.455(3) . ?
N9 C8 1.448(3) . ?
N10 C10 1.454(3) . ?
N11 C12 1.445(3) . ?
N12 C14 1.454(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.443(3) . ?
C3 C8 1.450(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.440(4) . ?
C9 C14 1.460(3) . ?
C10 C11 1.378(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C13 C14 1.378(3) . ?
C13 H13 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
H15A O15 H15B 108(4) . . ?
C1 N1 N2 103.1(2) . . ?
C2 N2 N1 112.5(2) . . ?
C2 N2 H2N 127(3) . . ?
N1 N2 H2N 121(3) . . ?
C2 N3 C1 106.1(2) . . ?
C2 N3 N4 130.6(2) . . ?
C1 N3 N4 123.0(2) . . ?
N3 N4 H4A 106(2) . . ?
N3 N4 H4B 107(2) . . ?
H4A N4 H4B 108(3) . . ?
C1 N5 N6 111.41(19) . . ?
C1 N5 H5N 115(2) . . ?
N6 N5 H5N 114(2) . . ?
N5 N6 H6A 107.9(19) . . ?
N5 N6 H6B 111.0(19) . . ?
H6A N6 H6B 111(3) . . ?
N5 N6 H6C 110(2) . . ?
H6A N6 H6C 106(3) . . ?
H6B N6 H6C 111(3) . . ?
O2 N7 O3 122.8(2) . . ?
O2 N7 C4 118.8(2) . . ?
O3 N7 C4 118.4(2) . . ?
O4 N8 O5 123.9(2) . . ?
O4 N8 C6 118.1(2) . . ?
O5 N8 C6 118.0(2) . . ?
O7 N9 O6 122.5(2) . . ?
O7 N9 C8 119.8(2) . . ?
O6 N9 C8 117.7(2) . . ?
O9 N10 O10 122.4(2) . . ?
O9 N10 C10 120.0(2) . . ?
O10 N10 C10 117.7(2) . . ?
O11 N11 O12 122.9(2) . . ?
O11 N11 C12 118.5(2) . . ?
O12 N11 C12 118.6(2) . . ?
O14 N12 O13 123.5(2) . . ?
O14 N12 C14 119.1(2) . . ?
O13 N12 C14 117.4(2) . . ?
N1 C1 N3 111.8(2) . . ?
N1 C1 N5 127.1(2) . . ?
N3 C1 N5 121.0(2) . . ?
N2 C2 N3 106.4(2) . . ?
N2 C2 H2 126.8 . . ?
N3 C2 H2 126.8 . . ?
O1 C3 C4 123.7(2) . . ?
O1 C3 C8 124.0(2) . . ?
C4 C3 C8 112.08(19) . . ?
C5 C4 C3 124.8(2) . . ?
C5 C4 N7 116.2(2) . . ?
C3 C4 N7 118.90(19) . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 122.0(2) . . ?
C7 C6 N8 119.6(2) . . ?
C5 C6 N8 118.4(2) . . ?
C8 C7 C6 118.7(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 N9 115.8(2) . . ?
C7 C8 C3 124.2(2) . . ?
N9 C8 C3 119.93(19) . . ?
O8 C9 C10 125.3(2) . . ?
O8 C9 C14 122.7(2) . . ?
C10 C9 C14 111.8(2) . . ?
C11 C10 C9 124.8(2) . . ?
C11 C10 N10 116.0(2) . . ?
C9 C10 N10 119.0(2) . . ?
C10 C11 C12 118.8(2) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 N11 119.6(2) . . ?
C11 C12 N11 119.0(2) . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 N12 116.4(2) . . ?
C13 C14 C9 123.9(2) . . ?
N12 C14 C9 119.6(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
C1 N1 N2 C2 0.7(3) . . . . ?
N2 N1 C1 N3 -0.5(2) . . . . ?
N2 N1 C1 N5 175.2(2) . . . . ?
C2 N3 C1 N1 0.1(3) . . . . ?
N4 N3 C1 N1 175.44(19) . . . . ?
C2 N3 C1 N5 -175.9(2) . . . . ?
N4 N3 C1 N5 -0.5(3) . . . . ?
N6 N5 C1 N1 0.6(3) . . . . ?
N6 N5 C1 N3 175.92(19) . . . . ?
N1 N2 C2 N3 -0.7(3) . . . . ?
C1 N3 C2 N2 0.3(3) . . . . ?
N4 N3 C2 N2 -174.5(2) . . . . ?
O1 C3 C4 C5 -173.7(2) . . . . ?
C8 C3 C4 C5 1.0(3) . . . . ?
O1 C3 C4 N7 4.2(3) . . . . ?
C8 C3 C4 N7 178.9(2) . . . . ?
O2 N7 C4 C5 -139.9(2) . . . . ?
O3 N7 C4 C5 37.7(3) . . . . ?
O2 N7 C4 C3 42.0(3) . . . . ?
O3 N7 C4 C3 -140.4(2) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
N7 C4 C5 C6 179.8(2) . . . . ?
C4 C5 C6 C7 2.3(4) . . . . ?
C4 C5 C6 N8 -177.8(2) . . . . ?
O4 N8 C6 C7 177.1(2) . . . . ?
O5 N8 C6 C7 -1.9(3) . . . . ?
O4 N8 C6 C5 -2.7(3) . . . . ?
O5 N8 C6 C5 178.2(2) . . . . ?
C5 C6 C7 C8 -1.2(4) . . . . ?
N8 C6 C7 C8 178.9(2) . . . . ?
C6 C7 C8 N9 176.3(2) . . . . ?
C6 C7 C8 C3 -0.1(4) . . . . ?
O7 N9 C8 C7 151.9(2) . . . . ?
O6 N9 C8 C7 -26.9(3) . . . . ?
O7 N9 C8 C3 -31.6(3) . . . . ?
O6 N9 C8 C3 149.6(2) . . . . ?
O1 C3 C8 C7 174.8(2) . . . . ?
C4 C3 C8 C7 0.2(3) . . . . ?
O1 C3 C8 N9 -1.4(4) . . . . ?
C4 C3 C8 N9 -176.1(2) . . . . ?
O8 C9 C10 C11 175.9(2) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
O8 C9 C10 N10 0.0(4) . . . . ?
C14 C9 C10 N10 -175.4(2) . . . . ?
O9 N10 C10 C11 154.1(3) . . . . ?
O10 N10 C10 C11 -26.4(3) . . . . ?
O9 N10 C10 C9 -29.6(4) . . . . ?
O10 N10 C10 C9 149.9(3) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
N10 C10 C11 C12 176.9(2) . . . . ?
C10 C11 C12 C13 -2.5(4) . . . . ?
C10 C11 C12 N11 -179.9(2) . . . . ?
O11 N11 C12 C13 -179.5(2) . . . . ?
O12 N11 C12 C13 -0.6(4) . . . . ?
O11 N11 C12 C11 -2.1(3) . . . . ?
O12 N11 C12 C11 176.8(2) . . . . ?
C11 C12 C13 C14 2.6(4) . . . . ?
N11 C12 C13 C14 180.0(2) . . . . ?
C12 C13 C14 N12 -177.2(2) . . . . ?
C12 C13 C14 C9 -1.1(4) . . . . ?
O14 N12 C14 C13 -150.4(3) . . . . ?
O13 N12 C14 C13 27.8(3) . . . . ?
O14 N12 C14 C9 33.4(4) . . . . ?
O13 N12 C14 C9 -148.5(2) . . . . ?
O8 C9 C14 C13 -176.0(2) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
O8 C9 C14 N12 0.0(4) . . . . ?
C10 C9 C14 N12 175.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        31.50
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.161

####################################################################### 
# 
# 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_bn2551
_database_code_depnum_ccdc_archive 'CCDC 1406851'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-04-18 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 N8 O6'
_chemical_formula_weight         240.16

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                   7.9601(18)
_cell_length_b                   15.917(4)
_cell_length_c                   7.0960(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.398(3)
_cell_angle_gamma                90.00
_cell_volume                     862.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2943
_cell_measurement_theta_min      2.559
_cell_measurement_theta_max      29.131

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9393
_exptl_absorpt_correction_T_max  0.9623
_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            8609
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         29.13
_reflns_number_total             2316
_reflns_number_gt                2043
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0286P)²+0.5060P] 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     SHELXL
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2316
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0754
_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
N1 N 0.21159(14) 0.04354(7) 0.02272(15) 0.0162(2) Uani 1 1 d . . .
N2 N 0.32131(13) 0.04970(7) 0.21112(15) 0.0151(2) Uani 1 1 d . . .
N3 N 0.15553(13) 0.16293(6) 0.12367(14) 0.0126(2) Uani 1 1 d . . .
N4 N 0.07971(14) 0.24011(7) 0.15144(16) 0.0164(2) Uani 1 1 d . . .
N5 N 0.34551(13) 0.15853(7) 0.45117(15) 0.0133(2) Uani 1 1 d . . .
N8 N 0.84494(13) 0.07362(7) 0.42656(15) 0.0153(2) Uani 1 1 d . . .
C1 C 0.11412(16) 0.11027(8) -0.03041(18) 0.0153(2) Uani 1 1 d . . .
H1 H 0.0305 0.1197 -0.1537 0.018 Uiso 1 1 calc R . .
C2 C 0.28229(15) 0.12344(7) 0.26805(17) 0.0125(2) Uani 1 1 d . . .
N6 N 0.46735(14) 0.10571(7) 0.58746(16) 0.0152(2) Uani 1 1 d . . .
N7 N 0.63161(14) 0.17979(6) 1.03732(15) 0.0152(2) Uani 1 1 d . . .
O1 O 0.46896(11) 0.17783(6) 0.93968(13) 0.0174(2) Uani 1 1 d . . .
O2 O 0.73651(12) 0.13595(6) 0.97939(13) 0.0191(2) Uani 1 1 d . . .
O3 O 0.67947(14) 0.22541(7) 1.18264(15) 0.0302(3) Uani 1 1 d . . .
O4 O 0.81560(13) 0.10991(6) 0.57162(14) 0.0233(2) Uani 1 1 d . . .
O5 O 0.72635(12) 0.02775(6) 0.31969(13) 0.0213(2) Uani 1 1 d . . .
O6 O 0.98504(13) 0.08343(7) 0.38857(16) 0.0291(3) Uani 1 1 d . . .
H1N H 0.221(2) 0.0012(12) -0.053(3) 0.034(5) Uiso 1 1 d . . .
H4A H 0.087(2) 0.2741(11) 0.054(3) 0.025(4) Uiso 1 1 d . . .
H4B H -0.036(3) 0.2292(11) 0.131(3) 0.034(5) Uiso 1 1 d . . .
H5 H 0.384(2) 0.2099(11) 0.454(2) 0.022(4) Uiso 1 1 d . . .
H6A H 0.414(2) 0.0538(11) 0.593(2) 0.027(4) Uiso 1 1 d . . .
H6B H 0.578(3) 0.1004(11) 0.564(3) 0.037(5) Uiso 1 1 d . . .
H6C H 0.484(2) 0.1305(11) 0.714(3) 0.029(4) 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
N1 C1 1.3065(16) . ?
N1 N2 1.3785(15) . ?
N1 H1N 0.878(19) . ?
N2 C2 1.3071(16) . ?
N3 C1 1.3429(16) . ?
N3 C2 1.3708(15) . ?
N3 N4 1.4068(14) . ?
N4 H4A 0.894(18) . ?
N4 H4B 0.908(19) . ?
N5 C2 1.3728(15) . ?
N5 N6 1.4329(14) . ?
N5 H5 0.871(17) . ?
N8 O6 1.2290(14) . ?
N8 O4 1.2584(14) . ?
N8 O5 1.2629(13) . ?
C1 H1 0.9500 . ?
N6 H6A 0.936(18) . ?
N6 H6B 0.949(19) . ?
N6 H6C 0.954(18) . ?
N7 O3 1.2304(14) . ?
N7 O2 1.2438(14) . ?
N7 O1 1.2848(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 112.58(10) . . ?
C1 N1 H1N 126.3(12) . . ?
N2 N1 H1N 120.6(12) . . ?
C2 N2 N1 102.88(10) . . ?
C1 N3 C2 106.38(10) . . ?
C1 N3 N4 130.00(10) . . ?
C2 N3 N4 123.37(10) . . ?
N3 N4 H4A 107.1(11) . . ?
N3 N4 H4B 105.5(12) . . ?
H4A N4 H4B 106.3(15) . . ?
C2 N5 N6 113.42(10) . . ?
C2 N5 H5 115.7(11) . . ?
N6 N5 H5 111.8(11) . . ?
O6 N8 O4 120.70(11) . . ?
O6 N8 O5 120.83(11) . . ?
O4 N8 O5 118.47(10) . . ?
N1 C1 N3 106.46(11) . . ?
N1 C1 H1 126.8 . . ?
N3 C1 H1 126.8 . . ?
N2 C2 N3 111.70(10) . . ?
N2 C2 N5 127.04(11) . . ?
N3 C2 N5 121.11(11) . . ?
N5 N6 H6A 108.5(10) . . ?
N5 N6 H6B 114.8(11) . . ?
H6A N6 H6B 112.8(15) . . ?
N5 N6 H6C 106.3(10) . . ?
H6A N6 H6C 105.6(14) . . ?
H6B N6 H6C 108.2(15) . . ?
O3 N7 O2 122.02(11) . . ?
O3 N7 O1 119.52(11) . . ?
O2 N7 O1 118.45(10) . . ?

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 N1 N2 C2 0.70(13) . . . . ?
N2 N1 C1 N3 -0.61(14) . . . . ?
C2 N3 C1 N1 0.26(13) . . . . ?
N4 N3 C1 N1 -173.94(11) . . . . ?
N1 N2 C2 N3 -0.51(13) . . . . ?
N1 N2 C2 N5 175.05(11) . . . . ?
C1 N3 C2 N2 0.18(13) . . . . ?
N4 N3 C2 N2 174.87(10) . . . . ?
C1 N3 C2 N5 -175.69(10) . . . . ?
N4 N3 C2 N5 -1.00(17) . . . . ?
N6 N5 C2 N2 0.33(17) . . . . ?
N6 N5 C2 N3 175.51(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_bn1964
_database_code_depnum_ccdc_archive 'CCDC 1406854'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H8 N10 O3'
_chemical_formula_weight         244.20

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                   12.455(4)
_cell_length_b                   7.156(2)
_cell_length_c                   22.215(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.497(4)
_cell_angle_gamma                90.00
_cell_volume                     1925.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7079
_cell_measurement_theta_min      2.214
_cell_measurement_theta_max      31.502

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_T_max  0.9788
_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            18664
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         31.52
_reflns_number_total             6392
_reflns_number_gt                5124
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0859P)²+0.5630P] 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         6392
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1455
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.09536(11) -0.04821(18) 0.12509(6) 0.0219(3) Uani 1 1 d . . .
O2 O 0.13868(10) 0.46995(19) -0.05938(6) 0.0223(3) Uani 1 1 d . . .
O3 O 0.11335(11) 0.58342(17) 0.02708(6) 0.0225(3) Uani 1 1 d . . .
O4 O 0.40880(10) 0.58860(18) 0.39151(6) 0.0213(3) Uani 1 1 d . . .
O5 O 0.35380(11) 1.11813(19) 0.57029(6) 0.0242(3) Uani 1 1 d . . .
O6 O 0.37772(10) 1.22768(17) 0.48298(6) 0.0224(3) Uani 1 1 d . . .
N1 N 0.34331(12) 0.6003(2) 0.23365(7) 0.0230(3) Uani 1 1 d . . .
N2 N 0.28474(11) 0.6223(2) 0.27970(7) 0.0191(3) Uani 1 1 d . . .
N3 N 0.16375(11) 0.5836(2) 0.19418(6) 0.0171(3) Uani 1 1 d . . .
N4 N 0.05864(12) 0.5654(2) 0.15426(7) 0.0206(3) Uani 1 1 d . . .
N5 N 0.09427(13) 0.6234(2) 0.28372(7) 0.0242(3) Uani 1 1 d . . .
N6 N 0.12291(15) 0.6572(3) 0.34812(8) 0.0301(4) Uani 1 1 d . . .
N7 N 0.15562(13) 0.1212(2) 0.27342(7) 0.0242(3) Uani 1 1 d . . .
N8 N 0.21613(12) 0.0816(2) 0.22961(7) 0.0207(3) Uani 1 1 d . . .
N9 N 0.33361(11) 0.1602(2) 0.31305(7) 0.0179(3) Uani 1 1 d . . .
N10 N 0.43732(12) 0.1940(2) 0.35334(7) 0.0208(3) Uani 1 1 d . . .
N11 N 0.40643(12) 0.0812(2) 0.22624(7) 0.0243(3) Uani 1 1 d . . .
N12 N 0.37731(14) 0.0211(3) 0.16381(7) 0.0242(3) Uani 1 1 d . . .
N13 N 0.13032(12) -0.0181(2) 0.02653(7) 0.0202(3) Uani 1 1 d . . .
N14 N 0.13794(12) 0.1211(2) -0.01434(7) 0.0193(3) Uani 1 1 d . . .
N15 N 0.09930(11) 0.2398(2) 0.07424(6) 0.0174(3) Uani 1 1 d . . .
N16 N 0.12345(11) 0.4515(2) -0.00707(7) 0.0169(3) Uani 1 1 d . . .
N17 N 0.37269(13) 0.6251(2) 0.48927(7) 0.0202(3) Uani 1 1 d . . .
N18 N 0.36076(12) 0.7661(2) 0.52835(7) 0.0199(3) Uani 1 1 d . . .
N19 N 0.39197(11) 0.8810(2) 0.43756(6) 0.0172(3) Uani 1 1 d . . .
N20 N 0.36789(11) 1.0974(2) 0.51769(7) 0.0173(3) Uani 1 1 d . . .
C1 C 0.26767(14) 0.5808(3) 0.18286(8) 0.0218(3) Uani 1 1 d . . .
H1 H 0.2822 0.5665 0.1430 0.026 Uiso 1 1 calc R . .
C2 C 0.17671(14) 0.6105(2) 0.25560(8) 0.0175(3) Uani 1 1 d . . .
C3 C 0.22895(14) 0.1659(3) 0.32295(8) 0.0232(4) Uani 1 1 d . . .
H3 H 0.2124 0.1984 0.3612 0.028 Uiso 1 1 calc R . .
C4 C 0.32354(13) 0.1050(2) 0.25367(8) 0.0169(3) Uani 1 1 d . . .
C5 C 0.10675(13) 0.0512(2) 0.07977(8) 0.0180(3) Uani 1 1 d . . .
C6 C 0.11882(13) 0.2661(2) 0.01761(8) 0.0164(3) Uani 1 1 d . . .
C7 C 0.39188(13) 0.6912(2) 0.43473(8) 0.0168(3) Uani 1 1 d . . .
C8 C 0.37293(13) 0.9105(2) 0.49401(8) 0.0159(3) Uani 1 1 d . . .
H2 H 0.327(2) 0.623(4) 0.3242(11) 0.039(7) Uiso 1 1 d . . .
H5 H 0.024(2) 0.628(4) 0.2613(11) 0.035(7) Uiso 1 1 d . . .
H4A H 0.0643(17) 0.468(3) 0.1275(10) 0.021(5) Uiso 1 1 d . . .
H4B H 0.0475(19) 0.683(3) 0.1328(11) 0.030(6) Uiso 1 1 d . . .
H6A H 0.084(2) 0.579(4) 0.3655(13) 0.043(8) Uiso 1 1 d . . .
H6B H 0.104(2) 0.772(5) 0.3523(14) 0.055(9) Uiso 1 1 d . . .
H8 H 0.176(2) 0.042(4) 0.1883(12) 0.042(7) Uiso 1 1 d . . .
H10A H 0.441(2) 0.096(4) 0.3845(13) 0.043(7) Uiso 1 1 d . . .
H10B H 0.4331(19) 0.309(4) 0.3709(11) 0.033(6) Uiso 1 1 d . . .
H11 H 0.473(2) 0.100(4) 0.2471(12) 0.039(7) Uiso 1 1 d . . .
H12A H 0.409(2) 0.104(4) 0.1410(13) 0.044(8) Uiso 1 1 d . . .
H12B H 0.406(2) -0.100(4) 0.1643(12) 0.039(7) Uiso 1 1 d . . .
H13 H 0.145(2) -0.143(4) 0.0183(12) 0.040(7) Uiso 1 1 d . . .
H17 H 0.3686(18) 0.503(4) 0.4987(10) 0.027(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 C5 1.267(2) . ?
O2 N16 1.2275(18) . ?
O3 N16 1.2356(19) . ?
O4 C7 1.265(2) . ?
O5 N20 1.2304(19) . ?
O6 N20 1.2342(19) . ?
N1 C1 1.298(2) . ?
N1 N2 1.397(2) . ?
N2 C2 1.330(2) . ?
N2 H2 1.01(2) . ?
N3 C2 1.350(2) . ?
N3 C1 1.375(2) . ?
N3 N4 1.406(2) . ?
N4 H4A 0.93(2) . ?
N4 H4B 0.96(2) . ?
N5 C2 1.324(2) . ?
N5 N6 1.412(2) . ?
N5 H5 0.90(2) . ?
N6 H6A 0.88(3) . ?
N6 H6B 0.86(3) . ?
N7 C3 1.295(2) . ?
N7 N8 1.392(2) . ?
N8 C4 1.330(2) . ?
N8 H8 0.98(3) . ?
N9 C4 1.354(2) . ?
N9 C3 1.372(2) . ?
N9 N10 1.410(2) . ?
N10 H10A 0.98(3) . ?
N10 H10B 0.92(3) . ?
N11 C4 1.327(2) . ?
N11 N12 1.416(2) . ?
N11 H11 0.86(3) . ?
N12 H12A 0.93(3) . ?
N12 H12B 0.94(3) . ?
N13 N14 1.366(2) . ?
N13 C5 1.376(2) . ?
N13 H13 0.94(3) . ?
N14 C6 1.310(2) . ?
N15 C6 1.349(2) . ?
N15 C5 1.356(2) . ?
N16 C6 1.442(2) . ?
N17 N18 1.361(2) . ?
N17 C7 1.373(2) . ?
N17 H17 0.90(3) . ?
N18 C8 1.314(2) . ?
N19 C8 1.346(2) . ?
N19 C7 1.359(2) . ?
N20 C8 1.444(2) . ?
C1 H1 0.9500 . ?
C3 H3 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
C1 N1 N2 104.57(14) . . ?
C2 N2 N1 110.50(14) . . ?
C2 N2 H2 130.1(14) . . ?
N1 N2 H2 118.5(14) . . ?
C2 N3 C1 106.94(14) . . ?
C2 N3 N4 121.68(14) . . ?
C1 N3 N4 131.38(15) . . ?
N3 N4 H4A 106.0(13) . . ?
N3 N4 H4B 103.7(14) . . ?
H4A N4 H4B 111.3(19) . . ?
C2 N5 N6 116.72(15) . . ?
C2 N5 H5 120.0(16) . . ?
N6 N5 H5 122.5(16) . . ?
N5 N6 H6A 107.4(18) . . ?
N5 N6 H6B 105(2) . . ?
H6A N6 H6B 111(3) . . ?
C3 N7 N8 104.75(15) . . ?
C4 N8 N7 110.57(15) . . ?
C4 N8 H8 131.5(15) . . ?
N7 N8 H8 117.9(15) . . ?
C4 N9 C3 106.81(14) . . ?
C4 N9 N10 122.08(14) . . ?
C3 N9 N10 131.06(15) . . ?
N9 N10 H10A 102.3(16) . . ?
N9 N10 H10B 106.7(15) . . ?
H10A N10 H10B 110(2) . . ?
C4 N11 N12 116.10(15) . . ?
C4 N11 H11 119.0(18) . . ?
N12 N11 H11 124.9(18) . . ?
N11 N12 H12A 107.2(17) . . ?
N11 N12 H12B 105.1(16) . . ?
H12A N12 H12B 113(2) . . ?
N14 N13 C5 111.74(14) . . ?
N14 N13 H13 121.1(16) . . ?
C5 N13 H13 127.0(16) . . ?
C6 N14 N13 99.67(14) . . ?
C6 N15 C5 101.54(14) . . ?
O2 N16 O3 124.02(15) . . ?
O2 N16 C6 119.19(14) . . ?
O3 N16 C6 116.78(14) . . ?
N18 N17 C7 112.01(14) . . ?
N18 N17 H17 123.3(15) . . ?
C7 N17 H17 124.7(15) . . ?
C8 N18 N17 99.66(14) . . ?
C8 N19 C7 101.61(14) . . ?
O5 N20 O6 123.99(15) . . ?
O5 N20 C8 119.07(14) . . ?
O6 N20 C8 116.94(14) . . ?
N1 C1 N3 111.27(16) . . ?
N1 C1 H1 124.4 . . ?
N3 C1 H1 124.4 . . ?
N5 C2 N2 128.98(16) . . ?
N5 C2 N3 124.33(16) . . ?
N2 C2 N3 106.68(14) . . ?
N7 C3 N9 111.37(16) . . ?
N7 C3 H3 124.3 . . ?
N9 C3 H3 124.3 . . ?
N11 C4 N8 128.08(16) . . ?
N11 C4 N9 125.43(15) . . ?
N8 C4 N9 106.49(14) . . ?
O1 C5 N15 127.78(16) . . ?
O1 C5 N13 124.49(16) . . ?
N15 C5 N13 107.72(15) . . ?
N14 C6 N15 119.32(15) . . ?
N14 C6 N16 119.62(15) . . ?
N15 C6 N16 121.00(14) . . ?
O4 C7 N19 128.07(16) . . ?
O4 C7 N17 124.33(16) . . ?
N19 C7 N17 107.58(14) . . ?
N18 C8 N19 119.13(15) . . ?
N18 C8 N20 119.74(15) . . ?
N19 C8 N20 121.12(15) . . ?

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 N1 N2 C2 1.7(2) . . . . ?
C3 N7 N8 C4 -0.5(2) . . . . ?
C5 N13 N14 C6 0.32(18) . . . . ?
C7 N17 N18 C8 0.46(18) . . . . ?
N2 N1 C1 N3 -1.8(2) . . . . ?
C2 N3 C1 N1 1.4(2) . . . . ?
N4 N3 C1 N1 -179.07(17) . . . . ?
N6 N5 C2 N2 1.1(3) . . . . ?
N6 N5 C2 N3 -178.13(18) . . . . ?
N1 N2 C2 N5 179.81(18) . . . . ?
N1 N2 C2 N3 -0.88(19) . . . . ?
C1 N3 C2 N5 179.12(17) . . . . ?
N4 N3 C2 N5 -0.5(3) . . . . ?
C1 N3 C2 N2 -0.23(19) . . . . ?
N4 N3 C2 N2 -179.85(15) . . . . ?
N8 N7 C3 N9 1.0(2) . . . . ?
C4 N9 C3 N7 -1.1(2) . . . . ?
N10 N9 C3 N7 -178.58(17) . . . . ?
N12 N11 C4 N8 -0.9(3) . . . . ?
N12 N11 C4 N9 179.48(17) . . . . ?
N7 N8 C4 N11 -179.86(18) . . . . ?
N7 N8 C4 N9 -0.2(2) . . . . ?
C3 N9 C4 N11 -179.54(18) . . . . ?
N10 N9 C4 N11 -1.8(3) . . . . ?
C3 N9 C4 N8 0.75(19) . . . . ?
N10 N9 C4 N8 178.47(15) . . . . ?
C6 N15 C5 O1 179.81(16) . . . . ?
C6 N15 C5 N13 0.24(17) . . . . ?
N14 N13 C5 O1 -179.97(15) . . . . ?
N14 N13 C5 N15 -0.38(19) . . . . ?
N13 N14 C6 N15 -0.18(19) . . . . ?
N13 N14 C6 N16 177.26(14) . . . . ?
C5 N15 C6 N14 0.0(2) . . . . ?
C5 N15 C6 N16 -177.44(14) . . . . ?
O2 N16 C6 N14 4.4(2) . . . . ?
O3 N16 C6 N14 -174.46(15) . . . . ?
O2 N16 C6 N15 -178.21(14) . . . . ?
O3 N16 C6 N15 2.9(2) . . . . ?
C8 N19 C7 O4 -178.17(16) . . . . ?
C8 N19 C7 N17 0.14(17) . . . . ?
N18 N17 C7 O4 177.99(15) . . . . ?
N18 N17 C7 N19 -0.40(19) . . . . ?
N17 N18 C8 N19 -0.40(19) . . . . ?
N17 N18 C8 N20 -179.19(14) . . . . ?
C7 N19 C8 N18 0.2(2) . . . . ?
C7 N19 C8 N20 178.95(14) . . . . ?
O5 N20 C8 N18 1.1(2) . . . . ?
O6 N20 C8 N18 -178.63(15) . . . . ?
O5 N20 C8 N19 -177.71(15) . . . . ?
O6 N20 C8 N19 2.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        31.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_150619h
_database_code_depnum_ccdc_archive 'CCDC 1419320'
_audit_update_record             
;
2016-01-28 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H8 N16 O2'
_chemical_formula_weight         312.26

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.9720(6)
_cell_length_b                   8.1923(8)
_cell_length_c                   10.2690(9)
_cell_angle_alpha                90.3780(10)
_cell_angle_beta                 110.218(2)
_cell_angle_gamma                115.520(2)
_cell_volume                     558.28(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    605
_cell_measurement_theta_min      2.944
_cell_measurement_theta_max      22.661

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2784
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.1095
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1921
_reflns_number_gt                1095
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1788P)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     SHELXL
_refine_ls_extinction_coef       0.024(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1921
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.3041
_refine_ls_wR_factor_gt          0.2790
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
N1 N 0.4272(8) 0.2743(7) 0.7360(6) 0.0327(14) Uani 1 1 d . . .
N2 N 0.6197(8) 0.3428(8) 0.8073(6) 0.0366(14) Uani 1 1 d . . .
N3 N 0.6782(8) 0.5113(8) 0.8601(7) 0.0416(16) Uani 1 1 d . . .
N4 N 0.5246(8) 0.5485(8) 0.8268(6) 0.0379(15) Uani 1 1 d . . .
N5 N -0.0993(7) 0.5873(7) 0.6437(6) 0.0308(13) Uani 1 1 d . . .
N6 N -0.2879(8) 0.5264(8) 0.5644(6) 0.0389(15) Uani 1 1 d . . .
N7 N -0.3466(8) 0.3588(8) 0.5111(6) 0.0410(15) Uani 1 1 d . . .
N8 N -0.2000(8) 0.3142(8) 0.5520(6) 0.0393(16) Uani 1 1 d . . .
N9 N 0.1759(7) 0.3607(7) 0.6845(6) 0.0313(13) Uani 1 1 d . . .
N10 N 0.1464(8) 0.4932(7) 0.7052(6) 0.0322(14) Uani 1 1 d . . .
N11 N 0.9575(8) 0.1953(8) 0.9816(6) 0.0369(15) Uani 1 1 d . . .
H11 H 1.0610 0.2782 1.0493 0.044 Uiso 1 1 calc R . .
N12 N 0.9605(8) 0.1404(8) 0.8588(6) 0.0356(14) Uani 1 1 d . . .
N13 N 0.6660(7) -0.0059(7) 0.8660(5) 0.0268(13) Uani 1 1 d . . .
N14 N 0.4645(7) -0.1142(7) 0.8309(6) 0.0351(14) Uani 1 1 d . . .
H14A H 0.3963 -0.0861 0.7535 0.053 Uiso 1 1 d R . .
H14B H 0.4360 -0.2319 0.8141 0.053 Uiso 1 1 d R . .
N15 N 0.7058(8) -0.0661(7) 0.6619(5) 0.0346(15) Uani 1 1 d . . .
H15 H 0.5790 -0.1351 0.6154 0.042 Uiso 1 1 calc R . .
N16 N 0.8474(8) -0.0373(7) 0.6052(5) 0.0328(14) Uani 1 1 d . . .
H16A H 0.9391 0.0806 0.6307 0.049 Uiso 1 1 d R . .
H16B H 0.7866 -0.0659 0.5115 0.049 Uiso 1 1 d R . .
O1 O 0.3195(7) 0.1100(6) 0.6687(5) 0.0414(13) Uani 1 1 d . . .
O2 O 0.0082(7) 0.7488(7) 0.7169(5) 0.0468(14) Uani 1 1 d . . .
H2 H -0.0597 0.8037 0.7028 0.070 Uiso 1 1 calc R . .
C1 C 0.3690(9) 0.3973(9) 0.7474(7) 0.0295(15) Uani 1 1 d . . .
C2 C -0.0450(9) 0.4591(8) 0.6378(7) 0.0276(15) Uani 1 1 d . . .
C3 C 0.7787(9) 0.0195(9) 0.7918(7) 0.0294(15) Uani 1 1 d . . .
C4 C 0.7842(10) 0.1103(9) 0.9857(8) 0.0364(17) Uani 1 1 d . . .
H4 H 0.7479 0.1272 1.0597 0.044 Uiso 1 1 calc R . .


_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
N1 O1 1.268(7) . ?
N1 N2 1.297(7) . ?
N1 C1 1.298(8) . ?
N2 N3 1.296(8) . ?
N3 N4 1.319(7) . ?
N4 C1 1.304(9) . ?
N5 O2 1.271(7) . ?
N5 N6 1.294(7) . ?
N5 C2 1.305(8) . ?
N6 N7 1.290(8) . ?
N7 N8 1.306(7) . ?
N8 C2 1.297(8) . ?
N9 N10 1.237(7) . ?
N9 C1 1.338(7) . ?
N10 C2 1.336(8) . ?
N11 C4 1.268(8) . ?
N11 N12 1.348(7) . ?
N11 H11 0.8600 . ?
N12 C3 1.273(8) . ?
N13 C4 1.311(8) . ?
N13 C3 1.321(7) . ?
N13 N14 1.366(6) . ?
N14 H14A 0.8900 . ?
N14 H14B 0.8900 . ?
N15 C3 1.308(7) . ?
N15 N16 1.377(6) . ?
N15 H15 0.8600 . ?
N16 H16A 0.8900 . ?
N16 H16B 0.8900 . ?
O2 H2 0.8200 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 N2 122.7(5) . . ?
O1 N1 C1 127.7(6) . . ?
N2 N1 C1 109.6(5) . . ?
N3 N2 N1 105.4(5) . . ?
N2 N3 N4 111.2(6) . . ?
C1 N4 N3 104.7(6) . . ?
O2 N5 N6 122.3(5) . . ?
O2 N5 C2 127.6(5) . . ?
N6 N5 C2 110.1(5) . . ?
N7 N6 N5 104.5(5) . . ?
N6 N7 N8 112.1(6) . . ?
C2 N8 N7 105.1(6) . . ?
N10 N9 C1 113.3(5) . . ?
N9 N10 C2 113.3(5) . . ?
C4 N11 N12 112.1(6) . . ?
C4 N11 H11 124.0 . . ?
N12 N11 H11 124.0 . . ?
C3 N12 N11 102.5(5) . . ?
C4 N13 C3 105.9(6) . . ?
C4 N13 N14 122.9(6) . . ?
C3 N13 N14 130.9(5) . . ?
N13 N14 H14A 108.9 . . ?
N13 N14 H14B 109.2 . . ?
H14A N14 H14B 109.5 . . ?
C3 N15 N16 114.9(5) . . ?
C3 N15 H15 122.5 . . ?
N16 N15 H15 122.5 . . ?
N15 N16 H16A 109.3 . . ?
N15 N16 H16B 109.0 . . ?
H16A N16 H16B 109.5 . . ?
N5 O2 H2 109.5 . . ?
N1 C1 N4 109.0(6) . . ?
N1 C1 N9 121.6(6) . . ?
N4 C1 N9 129.4(6) . . ?
N8 C2 N5 108.1(5) . . ?
N8 C2 N10 130.7(6) . . ?
N5 C2 N10 121.0(6) . . ?
N12 C3 N15 124.8(6) . . ?
N12 C3 N13 112.5(6) . . ?
N15 C3 N13 122.6(6) . . ?
N11 C4 N13 107.0(6) . . ?
N11 C4 H4 126.5 . . ?
N13 C4 H4 126.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 N2 N3 179.6(5) . . . . ?
C1 N1 N2 N3 -1.2(7) . . . . ?
N1 N2 N3 N4 1.9(8) . . . . ?
N2 N3 N4 C1 -1.9(8) . . . . ?
O2 N5 N6 N7 -178.1(6) . . . . ?
C2 N5 N6 N7 0.3(7) . . . . ?
N5 N6 N7 N8 -1.4(8) . . . . ?
N6 N7 N8 C2 1.9(8) . . . . ?
C1 N9 N10 C2 177.4(5) . . . . ?
C4 N11 N12 C3 0.3(7) . . . . ?
O1 N1 C1 N4 179.3(6) . . . . ?
N2 N1 C1 N4 0.1(8) . . . . ?
O1 N1 C1 N9 -0.2(10) . . . . ?
N2 N1 C1 N9 -179.3(6) . . . . ?
N3 N4 C1 N1 1.0(8) . . . . ?
N3 N4 C1 N9 -179.6(6) . . . . ?
N10 N9 C1 N1 -179.5(6) . . . . ?
N10 N9 C1 N4 1.2(10) . . . . ?
N7 N8 C2 N5 -1.6(7) . . . . ?
N7 N8 C2 N10 -176.5(6) . . . . ?
O2 N5 C2 N8 179.2(6) . . . . ?
N6 N5 C2 N8 0.8(7) . . . . ?
O2 N5 C2 N10 -5.3(10) . . . . ?
N6 N5 C2 N10 176.3(6) . . . . ?
N9 N10 C2 N8 -2.7(10) . . . . ?
N9 N10 C2 N5 -177.0(6) . . . . ?
N11 N12 C3 N15 176.0(6) . . . . ?
N11 N12 C3 N13 -1.2(7) . . . . ?
N16 N15 C3 N12 9.2(9) . . . . ?
N16 N15 C3 N13 -173.8(5) . . . . ?
C4 N13 C3 N12 1.7(7) . . . . ?
N14 N13 C3 N12 176.3(6) . . . . ?
C4 N13 C3 N15 -175.6(6) . . . . ?
N14 N13 C3 N15 -1.0(10) . . . . ?
N12 N11 C4 N13 0.7(7) . . . . ?
C3 N13 C4 N11 -1.4(7) . . . . ?
N14 N13 C4 N11 -176.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.111
