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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may 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_bo3219
_audit_block_doi                 10.5517/cc13n5xv
_database_code_depnum_ccdc_archive 'CCDC 1032297'
_audit_update_record             
;
2014-11-03 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 N7 Na O7'
_chemical_formula_weight         275.14

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   17.882(5)
_cell_length_b                   6.0919(18)
_cell_length_c                   9.281(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1011.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    4077
_cell_measurement_theta_min      2.778
_cell_measurement_theta_max      31.492

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.8972
_exptl_absorpt_correction_T_max  0.9572
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(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            9667
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         31.50
_reflns_number_total             1816
_reflns_number_gt                1694
_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)+(0.0659P)²+0.2620P] 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       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1816
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Na1 Na 0.0000 0.5000 0.0000 0.02286(18) Uani 1 2 d S . .
O1 O 0.10430(6) 0.2500 0.00129(10) 0.0217(2) Uani 1 2 d S . .
O2 O 0.35392(6) 0.2500 0.03660(14) 0.0301(3) Uani 1 2 d S . .
O3 O 0.11796(8) 0.2500 0.67881(13) 0.0434(4) Uani 1 2 d S . .
O4 O 0.01780(7) 0.2500 0.54622(14) 0.0419(4) Uani 1 2 d S . .
O5 O 0.04796(6) 0.7500 -0.17047(12) 0.0256(3) Uani 1 2 d S . .
H3 H 0.0918(15) 0.7500 -0.202(3) 0.043(7) Uiso 1 2 d S . .
H4 H 0.0209(18) 0.7500 -0.244(3) 0.066(9) Uiso 1 2 d S . .
O6 O 0.05435(7) 0.7500 0.16555(12) 0.0242(2) Uani 1 2 d S . .
H1 H 0.1004(15) 0.7500 0.184(3) 0.040(7) Uiso 1 2 d S . .
H5 H 0.0347(17) 0.7500 0.243(3) 0.064(9) Uiso 1 2 d S . .
O7 O 0.29445(7) 0.2500 0.70922(14) 0.0300(3) Uani 1 2 d S . .
H2 H 0.2639(15) 0.2500 0.644(3) 0.044(7) Uiso 1 2 d S . .
H6 H 0.2722(15) 0.2500 0.785(3) 0.047(7) Uiso 1 2 d S . .
N1 N 0.23161(7) 0.2500 0.01114(13) 0.0201(3) Uani 1 2 d S . .
N2 N 0.29198(6) 0.2500 0.09821(14) 0.0209(3) Uani 1 2 d S . .
N3 N 0.29326(6) 0.2500 0.24223(14) 0.0218(3) Uani 1 2 d S . .
N4 N 0.20725(7) 0.2500 0.44177(13) 0.0211(3) Uani 1 2 d S . .
N5 N 0.09938(6) 0.2500 0.30699(13) 0.0195(2) Uani 1 2 d S . .
N6 N 0.16111(6) 0.2500 0.22129(12) 0.0173(2) Uani 1 2 d S . .
N7 N 0.08597(8) 0.2500 0.56345(13) 0.0262(3) Uani 1 2 d S . .
C1 C 0.16220(7) 0.2500 0.07100(14) 0.0173(3) Uani 1 2 d S . .
C2 C 0.22475(7) 0.2500 0.30167(15) 0.0179(3) Uani 1 2 d S . .
C3 C 0.13213(8) 0.2500 0.43400(14) 0.0199(3) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Na1 0.0180(3) 0.0213(3) 0.0292(3) 0.0005(2) -0.00208(19) -0.0005(2)
O1 0.0144(5) 0.0325(6) 0.0180(4) 0.000 -0.0034(3) 0.000
O2 0.0121(5) 0.0485(8) 0.0298(5) 0.000 0.0042(4) 0.000
O3 0.0339(7) 0.0802(11) 0.0161(5) 0.000 -0.0020(4) 0.000
O4 0.0198(6) 0.0793(11) 0.0265(6) 0.000 0.0044(4) 0.000
O5 0.0161(5) 0.0369(7) 0.0238(5) 0.000 0.0035(4) 0.000
O6 0.0194(5) 0.0319(6) 0.0214(5) 0.000 -0.0003(4) 0.000
O7 0.0194(5) 0.0473(8) 0.0233(5) 0.000 -0.0007(4) 0.000
N1 0.0134(5) 0.0281(6) 0.0187(5) 0.000 -0.0009(4) 0.000
N2 0.0130(5) 0.0278(6) 0.0219(6) 0.000 0.0003(4) 0.000
N3 0.0136(5) 0.0318(7) 0.0201(5) 0.000 -0.0022(4) 0.000
N4 0.0168(6) 0.0286(6) 0.0180(5) 0.000 -0.0028(4) 0.000
N5 0.0147(5) 0.0262(6) 0.0175(5) 0.000 0.0010(4) 0.000
N6 0.0120(5) 0.0235(6) 0.0164(5) 0.000 -0.0010(4) 0.000
N7 0.0233(6) 0.0374(7) 0.0178(5) 0.000 0.0022(4) 0.000
C1 0.0153(6) 0.0199(6) 0.0167(5) 0.000 -0.0003(4) 0.000
C2 0.0133(5) 0.0215(6) 0.0190(6) 0.000 -0.0028(4) 0.000
C3 0.0173(6) 0.0249(7) 0.0174(6) 0.000 0.0001(4) 0.000

_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
Na1 O5 2.3576(10) . ?
Na1 O5 2.3576(10) 5_565 ?
Na1 O6 2.3717(10) 5_565 ?
Na1 O6 2.3717(10) . ?
Na1 O1 2.4079(9) 5_565 ?
Na1 O1 2.4079(9) . ?
Na1 Na1 3.0459(9) 3_545 ?
Na1 Na1 3.0459(9) 3 ?
O1 C1 1.2209(16) . ?
O1 Na1 2.4079(9) 3_545 ?
O2 N2 1.2466(15) . ?
O3 N7 1.2139(17) . ?
O4 N7 1.2294(19) . ?
O5 Na1 2.3576(10) 3 ?
O5 H3 0.84(3) . ?
O5 H4 0.84(3) . ?
O6 Na1 2.3717(10) 3 ?
O6 H1 0.84(3) . ?
O6 H5 0.80(3) . ?
O7 H2 0.81(3) . ?
O7 H6 0.81(3) . ?
N1 N2 1.3484(17) . ?
N1 C1 1.3600(17) . ?
N2 N3 1.3370(18) . ?
N3 C2 1.3435(17) . ?
N4 C2 1.3374(18) . ?
N4 C3 1.3454(18) . ?
N5 C3 1.3163(18) . ?
N5 N6 1.3605(16) . ?
N6 C2 1.3608(16) . ?
N6 C1 1.3951(17) . ?
N7 C3 1.4577(19) . ?

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
O5 Na1 O5 180.0 . 5_565 ?
O5 Na1 O6 97.42(4) . 5_565 ?
O5 Na1 O6 82.58(4) 5_565 5_565 ?
O5 Na1 O6 82.58(4) . . ?
O5 Na1 O6 97.42(4) 5_565 . ?
O6 Na1 O6 180.0 5_565 . ?
O5 Na1 O1 82.52(3) . 5_565 ?
O5 Na1 O1 97.48(3) 5_565 5_565 ?
O6 Na1 O1 94.91(3) 5_565 5_565 ?
O6 Na1 O1 85.09(3) . 5_565 ?
O5 Na1 O1 97.48(3) . . ?
O5 Na1 O1 82.52(3) 5_565 . ?
O6 Na1 O1 85.09(3) 5_565 . ?
O6 Na1 O1 94.91(3) . . ?
O1 Na1 O1 180.0 5_565 . ?
O5 Na1 Na1 130.24(2) . 3_545 ?
O5 Na1 Na1 49.76(2) 5_565 3_545 ?
O6 Na1 Na1 50.05(2) 5_565 3_545 ?
O6 Na1 Na1 129.95(2) . 3_545 ?
O1 Na1 Na1 129.234(19) 5_565 3_545 ?
O1 Na1 Na1 50.766(19) . 3_545 ?
O5 Na1 Na1 49.76(2) . 3 ?
O5 Na1 Na1 130.24(2) 5_565 3 ?
O6 Na1 Na1 129.95(2) 5_565 3 ?
O6 Na1 Na1 50.05(2) . 3 ?
O1 Na1 Na1 50.766(19) 5_565 3 ?
O1 Na1 Na1 129.234(19) . 3 ?
Na1 Na1 Na1 180.0 3_545 3 ?
C1 O1 Na1 131.26(5) . 3_545 ?
C1 O1 Na1 131.26(5) . . ?
Na1 O1 Na1 78.47(4) 3_545 . ?
Na1 O5 Na1 80.48(4) 3 . ?
Na1 O5 H3 125.1(11) 3 . ?
Na1 O5 H3 125.1(11) . . ?
Na1 O5 H4 109.7(15) 3 . ?
Na1 O5 H4 109.7(15) . . ?
H3 O5 H4 105(3) . . ?
Na1 O6 Na1 79.90(4) . 3 ?
Na1 O6 H1 122.3(11) . . ?
Na1 O6 H1 122.3(11) 3 . ?
Na1 O6 H5 113.8(15) . . ?
Na1 O6 H5 113.8(15) 3 . ?
H1 O6 H5 104(3) . . ?
H2 O7 H6 108(2) . . ?
N2 N1 C1 119.07(12) . . ?
O2 N2 N3 116.32(12) . . ?
O2 N2 N1 115.88(12) . . ?
N3 N2 N1 127.80(12) . . ?
N2 N3 C2 113.26(11) . . ?
C2 N4 C3 100.46(11) . . ?
C3 N5 N6 99.36(11) . . ?
N5 N6 C2 110.98(11) . . ?
N5 N6 C1 126.58(11) . . ?
C2 N6 C1 122.44(11) . . ?
O3 N7 O4 125.59(14) . . ?
O3 N7 C3 117.40(14) . . ?
O4 N7 C3 117.02(13) . . ?
O1 C1 N1 123.89(12) . . ?
O1 C1 N6 121.20(12) . . ?
N1 C1 N6 114.91(11) . . ?
N4 C2 N3 127.78(12) . . ?
N4 C2 N6 109.71(12) . . ?
N3 C2 N6 122.51(13) . . ?
N5 C3 N4 119.49(13) . . ?
N5 C3 N7 119.10(13) . . ?
N4 C3 N7 121.42(13) . . ?

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
O5 Na1 O1 C1 87.02(10) . . . . ?
O5 Na1 O1 C1 -92.98(10) 5_565 . . . ?
O6 Na1 O1 C1 -176.12(10) 5_565 . . . ?
O6 Na1 O1 C1 3.88(10) . . . . ?
O1 Na1 O1 C1 84.3(3) 5_565 . . . ?
Na1 Na1 O1 C1 -135.76(11) 3_545 . . . ?
Na1 Na1 O1 C1 44.24(11) 3 . . . ?
O5 Na1 O1 Na1 -137.22(3) . . . 3_545 ?
O5 Na1 O1 Na1 42.78(3) 5_565 . . 3_545 ?
O6 Na1 O1 Na1 -40.36(3) 5_565 . . 3_545 ?
O6 Na1 O1 Na1 139.64(3) . . . 3_545 ?
O1 Na1 O1 Na1 -139.98(3) 5_565 . . 3_545 ?
Na1 Na1 O1 Na1 180.0 3 . . 3_545 ?
O5 Na1 O5 Na1 23(7) 5_565 . . 3 ?
O6 Na1 O5 Na1 137.58(4) 5_565 . . 3 ?
O6 Na1 O5 Na1 -42.43(4) . . . 3 ?
O1 Na1 O5 Na1 43.57(3) 5_565 . . 3 ?
O1 Na1 O5 Na1 -136.43(3) . . . 3 ?
Na1 Na1 O5 Na1 180.0 3_545 . . 3 ?
O5 Na1 O6 Na1 42.20(4) . . . 3 ?
O5 Na1 O6 Na1 -137.80(4) 5_565 . . 3 ?
O6 Na1 O6 Na1 108.10(8) 5_565 . . 3 ?
O1 Na1 O6 Na1 -40.87(3) 5_565 . . 3 ?
O1 Na1 O6 Na1 139.13(3) . . . 3 ?
Na1 Na1 O6 Na1 180.0 3_545 . . 3 ?
C1 N1 N2 O2 180.0 . . . . ?
C1 N1 N2 N3 0.0 . . . . ?
O2 N2 N3 C2 180.0 . . . . ?
N1 N2 N3 C2 0.0 . . . . ?
C3 N5 N6 C2 0.0 . . . . ?
C3 N5 N6 C1 180.0 . . . . ?
Na1 O1 C1 N1 122.71(7) 3_545 . . . ?
Na1 O1 C1 N1 -122.71(7) . . . . ?
Na1 O1 C1 N6 -57.29(7) 3_545 . . . ?
Na1 O1 C1 N6 57.29(7) . . . . ?
N2 N1 C1 O1 180.0 . . . . ?
N2 N1 C1 N6 0.0 . . . . ?
N5 N6 C1 O1 0.0 . . . . ?
C2 N6 C1 O1 180.0 . . . . ?
N5 N6 C1 N1 180.0 . . . . ?
C2 N6 C1 N1 0.0 . . . . ?
C3 N4 C2 N3 180.0 . . . . ?
C3 N4 C2 N6 0.0 . . . . ?
N2 N3 C2 N4 180.0 . . . . ?
N2 N3 C2 N6 0.0 . . . . ?
N5 N6 C2 N4 0.0 . . . . ?
C1 N6 C2 N4 180.0 . . . . ?
N5 N6 C2 N3 180.0 . . . . ?
C1 N6 C2 N3 0.0 . . . . ?
N6 N5 C3 N4 0.0 . . . . ?
N6 N5 C3 N7 180.0 . . . . ?
C2 N4 C3 N5 0.0 . . . . ?
C2 N4 C3 N7 180.0 . . . . ?
O3 N7 C3 N5 180.0 . . . . ?
O4 N7 C3 N5 0.0 . . . . ?
O3 N7 C3 N4 0.0 . . . . ?
O4 N7 C3 N4 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        31.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_bo3236
_audit_block_doi                 10.5517/cc13n5yw
_database_code_depnum_ccdc_archive 'CCDC 1032298'
_audit_update_record             
;
2014-11-03 deposited with the CCDC.
2014-12-01 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 H6 N10 O4'
_chemical_formula_weight         258.19

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                   10.426(4)
_cell_length_b                   5.185(2)
_cell_length_c                   17.876(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.238(5)
_cell_angle_gamma                90.00
_cell_volume                     960.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    3721
_cell_measurement_theta_min      1.965
_cell_measurement_theta_max      31.492

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9065
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(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            10973
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         31.49
_reflns_number_total             3161
_reflns_number_gt                2570
_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)+(0.0596P)²+0.2190P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3161
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.46147(9) 0.2409(2) 0.04142(6) 0.0256(2) Uani 1 1 d . . .
O2 O 0.16224(10) 0.8099(2) 0.09415(6) 0.0308(3) Uani 1 1 d . . .
O3 O 0.81285(11) 0.8604(2) 0.29049(6) 0.0331(3) Uani 1 1 d . . .
O4 O 0.87044(10) 0.5280(2) 0.22874(7) 0.0344(3) Uani 1 1 d . . .
N1 N 0.30492(11) 0.5247(2) 0.06631(6) 0.0226(2) Uani 1 1 d . . .
N2 N 0.27603(10) 0.7303(2) 0.10695(6) 0.0219(2) Uani 1 1 d . . .
N3 N 0.35178(11) 0.8584(2) 0.15819(6) 0.0224(2) Uani 1 1 d . . .
N4 N 0.57018(11) 0.8454(2) 0.21729(6) 0.0212(2) Uani 1 1 d . . .
N5 N 0.63668(10) 0.4960(2) 0.15192(6) 0.0199(2) Uani 1 1 d . . .
N6 N 0.51088(10) 0.5563(2) 0.12945(6) 0.0185(2) Uani 1 1 d . . .
N7 N 0.79150(11) 0.6893(2) 0.24405(6) 0.0232(2) Uani 1 1 d . . .
N8 N -0.27467(11) 0.0227(3) 0.06439(7) 0.0248(3) Uani 1 1 d . . .
H8A H -0.3286(19) -0.061(4) 0.0322(11) 0.033(5) Uiso 1 1 d . . .
H8B H -0.2972(19) 0.164(4) 0.0851(11) 0.037(5) Uiso 1 1 d . . .
N9 N -0.10767(12) -0.2447(3) 0.04108(7) 0.0287(3) Uani 1 1 d . . .
H9A H -0.018(2) -0.273(4) 0.0509(12) 0.042(5) Uiso 1 1 d . . .
H9B H -0.163(2) -0.330(4) 0.0057(12) 0.042(5) Uiso 1 1 d . . .
N10 N -0.07026(13) 0.1003(3) 0.12122(8) 0.0346(3) Uani 1 1 d . . .
H10A H 0.010(2) 0.059(4) 0.1294(12) 0.042(6) Uiso 1 1 d . . .
H10B H -0.100(2) 0.228(5) 0.1464(13) 0.054(6) Uiso 1 1 d . . .
C1 C 0.42678(12) 0.4265(3) 0.07610(7) 0.0198(2) Uani 1 1 d . . .
C2 C 0.47292(12) 0.7620(3) 0.16876(7) 0.0192(2) Uani 1 1 d . . .
C3 C 0.66224(12) 0.6761(3) 0.20348(7) 0.0196(3) Uani 1 1 d . . .
C4 C -0.15115(13) -0.0390(3) 0.07521(7) 0.0221(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0237(5) 0.0263(5) 0.0265(5) -0.0084(4) 0.0009(4) 0.0048(4)
O2 0.0210(5) 0.0378(6) 0.0333(5) -0.0013(5) 0.0009(4) 0.0128(4)
O3 0.0302(5) 0.0339(6) 0.0343(6) -0.0139(5) 0.0000(4) -0.0034(5)
O4 0.0230(5) 0.0419(7) 0.0371(6) -0.0129(5) -0.0022(4) 0.0098(4)
N1 0.0210(5) 0.0256(6) 0.0209(5) -0.0015(4) 0.0012(4) 0.0050(4)
N2 0.0200(5) 0.0246(6) 0.0212(5) 0.0017(4) 0.0033(4) 0.0065(4)
N3 0.0209(5) 0.0229(6) 0.0236(5) -0.0011(4) 0.0030(4) 0.0046(4)
N4 0.0222(5) 0.0201(5) 0.0215(5) -0.0016(4) 0.0041(4) 0.0019(4)
N5 0.0169(5) 0.0225(5) 0.0199(5) -0.0014(4) 0.0011(4) 0.0030(4)
N6 0.0177(5) 0.0202(5) 0.0175(5) -0.0011(4) 0.0018(4) 0.0042(4)
N7 0.0210(5) 0.0269(6) 0.0217(5) -0.0030(4) 0.0026(4) -0.0012(4)
N8 0.0209(5) 0.0259(6) 0.0278(6) -0.0026(5) 0.0027(4) 0.0063(5)
N9 0.0218(5) 0.0304(7) 0.0327(6) -0.0095(5) -0.0015(5) 0.0085(5)
N10 0.0264(6) 0.0370(8) 0.0385(7) -0.0161(6) -0.0058(5) 0.0087(6)
C1 0.0203(6) 0.0211(6) 0.0180(5) 0.0003(4) 0.0025(4) 0.0021(5)
C2 0.0216(6) 0.0175(6) 0.0190(5) 0.0014(4) 0.0046(4) 0.0033(5)
C3 0.0199(6) 0.0202(6) 0.0190(5) -0.0001(4) 0.0035(4) 0.0005(5)
C4 0.0219(6) 0.0235(6) 0.0208(6) 0.0005(5) 0.0014(4) 0.0045(5)

_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 1.2207(16) . ?
O2 N2 1.2535(15) . ?
O3 N7 1.2188(15) . ?
O4 N7 1.2250(16) . ?
N1 N2 1.3427(17) . ?
N1 C1 1.3624(17) . ?
N2 N3 1.3217(16) . ?
N3 C2 1.3525(17) . ?
N4 C2 1.3330(17) . ?
N4 C3 1.3432(17) . ?
N5 C3 1.3189(17) . ?
N5 N6 1.3656(15) . ?
N6 C2 1.3598(17) . ?
N6 C1 1.3962(16) . ?
N7 C3 1.4610(17) . ?
N8 C4 1.3208(18) . ?
N8 H8A 0.88(2) . ?
N8 H8B 0.86(2) . ?
N9 C4 1.3325(18) . ?
N9 H9A 0.95(2) . ?
N9 H9B 0.92(2) . ?
N10 C4 1.3263(19) . ?
N10 H10A 0.86(2) . ?
N10 H10B 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 C1 119.22(11) . . ?
O2 N2 N3 116.32(11) . . ?
O2 N2 N1 115.23(11) . . ?
N3 N2 N1 128.45(11) . . ?
N2 N3 C2 112.93(11) . . ?
C2 N4 C3 100.17(11) . . ?
C3 N5 N6 99.10(10) . . ?
C2 N6 N5 110.59(10) . . ?
C2 N6 C1 122.32(11) . . ?
N5 N6 C1 127.05(11) . . ?
O3 N7 O4 124.86(12) . . ?
O3 N7 C3 117.55(11) . . ?
O4 N7 C3 117.59(11) . . ?
C4 N8 H8A 121.5(13) . . ?
C4 N8 H8B 116.6(13) . . ?
H8A N8 H8B 121.2(18) . . ?
C4 N9 H9A 114.7(12) . . ?
C4 N9 H9B 118.6(13) . . ?
H9A N9 H9B 126.0(18) . . ?
C4 N10 H10A 120.7(14) . . ?
C4 N10 H10B 119.8(16) . . ?
H10A N10 H10B 119(2) . . ?
O1 C1 N1 123.58(12) . . ?
O1 C1 N6 121.88(12) . . ?
N1 C1 N6 114.54(11) . . ?
N4 C2 N3 127.15(12) . . ?
N4 C2 N6 110.32(11) . . ?
N3 C2 N6 122.53(12) . . ?
N5 C3 N4 119.81(12) . . ?
N5 C3 N7 119.04(11) . . ?
N4 C3 N7 121.15(12) . . ?
N8 C4 N10 120.19(13) . . ?
N8 C4 N9 120.12(13) . . ?
N10 C4 N9 119.67(13) . . ?

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 O2 179.46(12) . . . . ?
C1 N1 N2 N3 -0.4(2) . . . . ?
O2 N2 N3 C2 -179.81(12) . . . . ?
N1 N2 N3 C2 0.08(19) . . . . ?
C3 N5 N6 C2 -0.16(13) . . . . ?
C3 N5 N6 C1 -177.84(12) . . . . ?
N2 N1 C1 O1 -179.75(12) . . . . ?
N2 N1 C1 N6 0.02(18) . . . . ?
C2 N6 C1 O1 -179.53(13) . . . . ?
N5 N6 C1 O1 -2.1(2) . . . . ?
C2 N6 C1 N1 0.70(18) . . . . ?
N5 N6 C1 N1 178.13(12) . . . . ?
C3 N4 C2 N3 178.83(13) . . . . ?
C3 N4 C2 N6 -0.52(14) . . . . ?
N2 N3 C2 N4 -178.60(12) . . . . ?
N2 N3 C2 N6 0.68(18) . . . . ?
N5 N6 C2 N4 0.47(15) . . . . ?
C1 N6 C2 N4 178.27(11) . . . . ?
N5 N6 C2 N3 -178.92(12) . . . . ?
C1 N6 C2 N3 -1.12(19) . . . . ?
N6 N5 C3 N4 -0.20(15) . . . . ?
N6 N5 C3 N7 -179.51(11) . . . . ?
C2 N4 C3 N5 0.47(16) . . . . ?
C2 N4 C3 N7 179.76(12) . . . . ?
O3 N7 C3 N5 178.83(12) . . . . ?
O4 N7 C3 N5 -0.97(18) . . . . ?
O3 N7 C3 N4 -0.47(19) . . . . ?
O4 N7 C3 N4 179.73(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        31.49
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.051
