# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_bwn16030
_database_code_depnum_ccdc_archive 'CCDC 1479505'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2016-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H6 N9 Na O3, 2(H2 O)'
_chemical_formula_sum            'C3 H10 N9 Na O5'
_chemical_formula_weight         275.19
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x+1/2, -y, z+1/2'

_cell_length_a                   11.797(2)
_cell_length_b                   3.5480(7)
_cell_length_c                   13.404(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.25(3)
_cell_angle_gamma                90.00
_cell_volume                     538.65(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1933
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.5824
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9384
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5918
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.71
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.7937
	          2theta: -20.1783
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.7937
	          2theta: -20.1783
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.7937
	          2theta: -20.1783
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             1436
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0025
_diffrn_orient_matrix_UB_12      0.0835
_diffrn_orient_matrix_UB_13      -0.0287
_diffrn_orient_matrix_UB_21      0.2808
_diffrn_orient_matrix_UB_22      0.0149
_diffrn_orient_matrix_UB_23      0.0186
_diffrn_orient_matrix_UB_31      0.0053
_diffrn_orient_matrix_UB_32      -0.0034
_diffrn_orient_matrix_UB_33      -0.0774
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2393
_reflns_number_total             2434
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.164
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.229
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0770P)²+0.0550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1223
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1(H1A,H1B), O2(H2A,H2B), O3(H3A,H3B), O4(H4A,H4B), O5(H5), N8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Na1 Na 0.58192(8) 0.4608(3) 0.58902(7) 0.0162(2) Uani 1 d . . .
O1 O 0.71738(15) 0.9427(5) 0.64851(14) 0.0181(4) Uani 1 d . . .
H1A H 0.7528 1.0027 0.7099 0.022 Uiso 1 d . . R
H1B H 0.7544 0.9819 0.6043 0.022 Uiso 1 d . . R
O2 O 0.44021(15) -0.0256(5) 0.54130(14) 0.0189(4) Uani 1 d . . .
H2A H 0.3907 0.0064 0.5750 0.023 Uiso 1 d . . R
H2B H 0.4058 -0.0307 0.4773 0.023 Uiso 1 d . . R
O3 O 0.33757(16) 0.7527(5) 0.34014(15) 0.0187(4) Uani 1 d . . .
H3A H 0.2829 0.6077 0.3445 0.022 Uiso 1 d . . R
H3B H 0.3936 0.6167 0.3341 0.022 Uiso 1 d . . R
O4 O 0.24193(15) 0.2078(5) 0.60970(13) 0.0182(4) Uani 1 d . . .
H4A H 0.2248 0.0602 0.6523 0.022 Uiso 1 d . . R
H4B H 0.2342 0.4269 0.6306 0.022 Uiso 1 d . . R
O5 O 0.49286(15) 1.0166(6) 1.06604(14) 0.0205(4) Uani 1 d . . .
H5 H 0.5026 1.0954 1.1270 0.025 Uiso 1 d . . R
N1 N 0.64839(17) 0.3823(6) 0.41976(15) 0.0145(4) Uani 1 d . . .
N2 N 0.54745(17) 0.3821(6) 0.34300(17) 0.0152(4) Uani 1 d . . .
N3 N 0.56654(18) 0.2619(6) 0.25649(17) 0.0158(4) Uani 1 d . . .
N4 N 0.68171(17) 0.1793(6) 0.27313(16) 0.0153(4) Uani 1 d . . .
N5 N 0.42543(17) 0.5963(6) 0.77991(16) 0.0153(4) Uani 1 d . . .
N6 N 0.53277(18) 0.5200(6) 0.76634(16) 0.0173(4) Uani 1 d . . .
N7 N 0.61568(18) 0.5769(6) 0.85130(17) 0.0168(4) Uani 1 d . . .
N8 N 0.56398(17) 0.6957(6) 0.92305(16) 0.0146(4) Uani 1 d . . .
H8 H 0.5936 0.7760 0.9881 0.017 Uiso 1 d . . R
N9 N 0.37482(17) 0.9609(6) 1.01969(15) 0.0144(4) Uani 1 d . . .
C1 C 0.72878(19) 0.2536(6) 0.37349(17) 0.0124(4) Uani 1 d . . .
C2 C 0.4463(2) 0.7046(6) 0.87885(18) 0.0120(4) Uani 1 d . . .
C3 C 0.3546(2) 0.8097(6) 0.92876(17) 0.0129(4) Uani 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
Na1 Na1 3.5480(7) 1_565 ?
Na1 Na1 3.5480(7) 1_545 ?
Na1 O1 2.420(2) 1_545 ?
Na1 O1 2.324(2) . ?
Na1 O2 2.435(2) 1_565 ?
Na1 O2 2.363(2) . ?
Na1 N1 2.614(2) . ?
Na1 N6 2.608(2) . ?
O1 Na1 2.420(2) 1_565 ?
O1 H1A 0.8400 . ?
O1 H1B 0.8398 . ?
O2 Na1 2.435(2) 1_545 ?
O2 H2A 0.8402 . ?
O2 H2B 0.8400 . ?
O3 H3A 0.8399 . ?
O3 H3B 0.8400 . ?
O4 H4A 0.8401 . ?
O4 H4B 0.8400 . ?
O4 H4B 0.8400 . ?
O5 H5 0.8401 . ?
O5 N9 1.371(2) . ?
N1 N2 1.338(3) . ?
N1 C1 1.350(3) . ?
N2 N3 1.313(3) . ?
N3 N4 1.346(3) . ?
N4 C1 1.330(3) . ?
N5 N6 1.356(3) . ?
N5 C2 1.336(3) . ?
N6 N7 1.293(3) . ?
N7 N8 1.343(3) . ?
N8 H8 0.8901 . ?
N8 C2 1.349(3) . ?
N9 C3 1.291(3) . ?
C1 C3 1.479(3) 2_564 ?
C2 C3 1.470(3) . ?
C3 C1 1.479(3) 2_465 ?

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
Na1 Na1 Na1 180.00(3) 1_565 1_545 ?
O1 Na1 Na1 137.38(5) . 1_545 ?
O1 Na1 Na1 40.57(5) 1_545 1_545 ?
O1 Na1 Na1 139.43(5) 1_545 1_565 ?
O1 Na1 Na1 42.63(5) . 1_565 ?
O1 Na1 O1 96.81(7) . 1_545 ?
O1 Na1 O2 83.97(7) . 1_565 ?
O1 Na1 O2 175.46(7) 1_545 1_565 ?
O1 Na1 O2 175.39(8) . . ?
O1 Na1 N1 91.81(7) . . ?
O1 Na1 N1 82.78(7) 1_545 . ?
O1 Na1 N6 86.26(7) . . ?
O1 Na1 N6 93.19(7) 1_545 . ?
O2 Na1 Na1 41.53(5) 1_565 1_565 ?
O2 Na1 Na1 138.47(5) 1_565 1_545 ?
O2 Na1 Na1 43.09(5) . 1_545 ?
O2 Na1 Na1 136.91(5) . 1_565 ?
O2 Na1 O1 83.48(7) . 1_545 ?
O2 Na1 O2 95.38(7) . 1_565 ?
O2 Na1 N1 92.79(7) . . ?
O2 Na1 N1 101.67(7) 1_565 . ?
O2 Na1 N6 89.13(7) . . ?
O2 Na1 N6 82.39(7) 1_565 . ?
N1 Na1 Na1 96.11(5) . 1_565 ?
N1 Na1 Na1 83.89(5) . 1_545 ?
N6 Na1 Na1 94.63(5) . 1_545 ?
N6 Na1 Na1 85.37(5) . 1_565 ?
N6 Na1 N1 175.31(7) . . ?
Na1 O1 Na1 96.80(7) . 1_565 ?
Na1 O1 H1A 129.0 . . ?
Na1 O1 H1A 103.4 1_565 . ?
Na1 O1 H1B 108.8 . . ?
Na1 O1 H1B 93.9 1_565 . ?
H1A O1 H1B 115.8 . . ?
Na1 O2 Na1 95.38(7) . 1_545 ?
Na1 O2 H2A 107.6 . . ?
Na1 O2 H2A 119.3 1_545 . ?
Na1 O2 H2B 113.3 . . ?
Na1 O2 H2B 110.6 1_545 . ?
H2A O2 H2B 109.9 . . ?
H3A O3 H3B 107.2 . . ?
H4A O4 H4B 106.3 . . ?
H4B O4 H4A 106.3 . . ?
H4B O4 H4B 0.0 . . ?
N9 O5 H5 109.5 . . ?
N2 N1 Na1 104.41(14) . . ?
N2 N1 C1 103.59(18) . . ?
C1 N1 Na1 148.72(15) . . ?
N3 N2 N1 110.10(18) . . ?
N2 N3 N4 109.81(19) . . ?
C1 N4 N3 103.9(2) . . ?
C2 N5 N6 105.74(19) . . ?
N5 N6 Na1 126.33(16) . . ?
N7 N6 Na1 120.61(15) . . ?
N7 N6 N5 110.82(19) . . ?
N6 N7 N8 107.26(19) . . ?
N7 N8 H8 132.0 . . ?
N7 N8 C2 108.10(19) . . ?
C2 N8 H8 119.7 . . ?
C3 N9 O5 112.57(19) . . ?
N1 C1 C3 123.8(2) . 2_564 ?
N4 C1 N1 112.6(2) . . ?
N4 C1 C3 123.6(2) . 2_564 ?
N5 C2 N8 108.1(2) . . ?
N5 C2 C3 124.8(2) . . ?
N8 C2 C3 127.2(2) . . ?
N9 C3 C1 115.52(19) . 2_465 ?
N9 C3 C2 124.7(2) . . ?
C2 C3 C1 119.8(2) . 2_465 ?

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
Na1 Na1 O1 Na1 180.0 1_545 . . 1_565 ?
Na1 Na1 O2 Na1 179.999(2) 1_565 . . 1_545 ?
Na1 Na1 N1 N2 -88.47(13) 1_565 . . . ?
Na1 Na1 N1 N2 91.53(13) 1_545 . . . ?
Na1 Na1 N1 C1 118.6(3) 1_565 . . . ?
Na1 Na1 N1 C1 -61.4(3) 1_545 . . . ?
Na1 Na1 N6 N5 79.11(19) 1_565 . . . ?
Na1 Na1 N6 N5 -100.89(19) 1_545 . . . ?
Na1 Na1 N6 N7 -82.30(18) 1_565 . . . ?
Na1 Na1 N6 N7 97.71(18) 1_545 . . . ?
Na1 N1 N2 N3 -166.07(15) . . . . ?
Na1 N1 C1 N4 153.5(2) . . . . ?
Na1 N1 C1 C3 -24.6(4) . . . 2_564 ?
Na1 N6 N7 N8 163.60(14) . . . . ?
O1 Na1 O1 Na1 180.0 1_545 . . 1_565 ?
O1 Na1 O2 Na1 -4.42(7) 1_545 . . 1_545 ?
O1 Na1 O2 Na1 -98.3(10) . . . 1_545 ?
O1 Na1 N1 N2 132.38(14) 1_545 . . . ?
O1 Na1 N1 N2 -130.99(14) . . . . ?
O1 Na1 N1 C1 -20.5(3) 1_545 . . . ?
O1 Na1 N1 C1 76.1(3) . . . . ?
O1 Na1 N6 N5 -141.54(19) 1_545 . . . ?
O1 Na1 N6 N5 121.8(2) . . . . ?
O1 Na1 N6 N7 -39.56(19) . . . . ?
O1 Na1 N6 N7 57.06(19) 1_545 . . . ?
O2 Na1 O1 Na1 -86.7(10) . . . 1_565 ?
O2 Na1 O1 Na1 -4.50(7) 1_565 . . 1_565 ?
O2 Na1 O2 Na1 180.0 1_565 . . 1_545 ?
O2 Na1 N1 N2 -46.77(15) 1_565 . . . ?
O2 Na1 N1 N2 49.31(14) . . . . ?
O2 Na1 N1 C1 160.3(3) 1_565 . . . ?
O2 Na1 N1 C1 -103.6(3) . . . . ?
O2 Na1 N6 N5 37.43(19) 1_565 . . . ?
O2 Na1 N6 N5 -58.11(19) . . . . ?
O2 Na1 N6 N7 140.49(19) . . . . ?
O2 Na1 N6 N7 -123.97(19) 1_565 . . . ?
O5 N9 C3 C1 -179.16(19) . . . 2_465 ?
O5 N9 C3 C2 0.2(3) . . . . ?
N1 Na1 O1 Na1 97.05(7) . . . 1_565 ?
N1 Na1 O2 Na1 77.99(7) . . . 1_545 ?
N1 Na1 N6 N5 -172.3(9) . . . . ?
N1 Na1 N6 N7 26.3(11) . . . . ?
N1 N2 N3 N4 -0.2(3) . . . . ?
N2 N1 C1 N4 0.5(2) . . . . ?
N2 N1 C1 C3 -177.6(2) . . . 2_564 ?
N2 N3 N4 C1 0.5(3) . . . . ?
N3 N4 C1 N1 -0.6(3) . . . . ?
N3 N4 C1 C3 177.5(2) . . . 2_564 ?
N5 N6 N7 N8 -0.4(3) . . . . ?
N5 C2 C3 N9 -170.4(2) . . . . ?
N5 C2 C3 C1 8.9(3) . . . 2_465 ?
N6 Na1 O1 Na1 -87.23(8) . . . 1_565 ?
N6 Na1 O2 Na1 -97.72(7) . . . 1_545 ?
N6 Na1 N1 N2 163.4(9) . . . . ?
N6 Na1 N1 C1 10.5(11) . . . . ?
N6 N5 C2 N8 0.5(3) . . . . ?
N6 N5 C2 C3 -179.0(2) . . . . ?
N6 N7 N8 C2 0.7(3) . . . . ?
N7 N8 C2 N5 -0.7(3) . . . . ?
N7 N8 C2 C3 178.7(2) . . . . ?
N8 C2 C3 N9 10.3(4) . . . . ?
N8 C2 C3 C1 -170.4(2) . . . 2_465 ?
C1 N1 N2 N3 -0.2(2) . . . . ?
C2 N5 N6 Na1 -162.93(15) . . . . ?
C2 N5 N6 N7 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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. 
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#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1479506'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2016-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C3 H5 N9 Na O3), 2(H4 N O), H2 O'
_chemical_formula_sum            'C6 H20 N20 Na2 O9'
_chemical_formula_weight         562.40
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
Na Na 0.0362 0.0249 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'

_cell_length_a                   14.431(3)
_cell_length_b                   3.5670(7)
_cell_length_c                   22.642(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.56(2)
_cell_angle_gamma                90.00
_cell_volume                     1084.0(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3330
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.9343
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7123
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7962
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.52
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.8067
	          2theta: -20.1860
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.8067
	          2theta: -20.1860
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             2881
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0243
_diffrn_orient_matrix_UB_12      -0.0253
_diffrn_orient_matrix_UB_13      -0.0630
_diffrn_orient_matrix_UB_21      0.0075
_diffrn_orient_matrix_UB_22      0.2610
_diffrn_orient_matrix_UB_23      -0.1020
_diffrn_orient_matrix_UB_31      0.0474
_diffrn_orient_matrix_UB_32      -0.0001
_diffrn_orient_matrix_UB_33      0.0032
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2232
_reflns_number_total             2480
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.878
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.271
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         2480
_refine_ls_number_restraints     392
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1052P)²+1.0775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1903
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.01
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.01
3.a Riding coordinates:
 O6(H6A,H6B), N13(H13), O7(H7A,H7B), O3(H3A,H3B), O4(H4A,H4B), N3(H3), O1(H1),
 N21(H21A,H21B,H21C), O2(H2), N22(H22A,H22B,H22C), O5(H5A,H5B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Na1 Na 0.19990(18) -0.5803(7) 0.02254(13) 0.0236(6) Uani 1 d . . . U
O6 O 0.3115(3) -1.0867(13) 0.0698(2) 0.0221(9) Uani 1 d . . . U
H6A H 0.3347 -1.0213 0.1071 0.027 Uiso 1 d . . R .
H6B H 0.3507 -1.1762 0.0550 0.027 Uiso 1 d . . R .
O9 O 0.2136(3) -0.9824(13) -0.06420(16) 0.0151(8) Uani 1 d . . . U
N11 N 0.0532(3) -0.2115(14) -0.0433(2) 0.0127(9) Uani 1 d . . . U
N12 N -0.0220(3) -0.2311(14) -0.0216(2) 0.0142(9) Uani 1 d . . . U
N13 N -0.1015(3) -0.0792(13) -0.0637(2) 0.0129(9) Uani 1 d . . . U
H13 H -0.1583 -0.0607 -0.0595 0.015 Uiso 1 d . . R .
N14 N -0.0831(3) 0.0425(13) -0.1141(2) 0.0120(9) Uani 1 d . . . U
N15 N -0.0905(3) -0.9955(14) -0.2411(2) 0.0132(9) Uani 1 d . . . U
N16 N -0.1139(3) -0.8876(14) -0.3022(2) 0.0142(9) Uani 1 d . . . U
N17 N -0.0364(3) -0.7264(14) -0.3091(2) 0.0147(9) Uani 1 d . . . U
N18 N 0.0396(3) -0.7273(14) -0.2529(2) 0.0135(9) Uani 1 d . . . U
N19 N 0.1606(3) -0.9301(13) -0.1291(2) 0.0125(9) Uani 1 d . . . U
C4 C 0.0138(3) -0.0409(15) -0.1001(2) 0.0101(9) Uani 1 d . . . U
C5 C 0.0653(4) -0.9562(15) -0.1445(2) 0.0099(9) Uani 1 d . . . U
C6 C 0.0060(4) -0.8909(15) -0.2119(2) 0.0095(9) Uani 1 d . . . U
O7 O 0.1414(5) -0.730(3) 0.1051(3) 0.0582(19) Uani 1 d . . . U
H7A H 0.0943 -0.8839 0.0915 0.070 Uiso 1 d . . R .
H7B H 0.1210 -0.5333 0.1169 0.070 Uiso 1 d . . R .
Na2 Na 0.71820(18) -1.6232(7) 0.02696(12) 0.0205(5) Uani 1 d . . . U
O3 O 0.8918(4) -1.5980(14) 0.0632(2) 0.0267(10) Uani 1 d . . . U
H3A H 0.9161 -1.4934 0.0389 0.032 Uiso 1 d . . R .
H3B H 0.9122 -1.5044 0.0998 0.032 Uiso 1 d . . R .
O4 O 0.7010(3) -1.1252(12) 0.09156(19) 0.0198(9) Uani 1 d . . . U
H4A H 0.7553 -1.1213 0.1227 0.024 Uiso 1 d . . R .
H4B H 0.6446 -1.1889 0.0910 0.024 Uiso 1 d . . R .
O8 O 0.7164(3) -1.0780(13) -0.05887(18) 0.0165(8) Uani 1 d . . . U
N1 N 0.5515(3) -1.8119(13) -0.0430(2) 0.0115(8) Uani 1 d . . . U
N2 N 0.4763(3) -1.7779(13) -0.0217(2) 0.0131(8) Uani 1 d . . . U
N3 N 0.3970(3) -1.9418(13) -0.0632(2) 0.0121(8) Uani 1 d . . . U
H3 H 0.3402 -1.9571 -0.0591 0.014 Uiso 1 d . . R .
N4 N 0.4161(3) -2.0780(13) -0.1130(2) 0.0114(8) Uani 1 d . . . U
N5 N 0.4140(3) -1.0412(13) -0.2395(2) 0.0128(9) Uani 1 d . . . U
N6 N 0.3930(3) -1.1396(14) -0.3000(2) 0.0144(9) Uani 1 d . . . U
N7 N 0.4717(3) -1.3037(14) -0.3053(2) 0.0142(9) Uani 1 d . . . U
N8 N 0.5456(3) -1.3149(13) -0.2482(2) 0.0132(9) Uani 1 d . . . U
N9 N 0.6629(3) -1.1278(13) -0.1238(2) 0.0133(9) Uani 1 d . . . U
C1 C 0.5126(3) -1.9935(15) -0.0989(2) 0.0099(9) Uani 1 d . . . U
C2 C 0.5671(4) -1.0928(15) -0.1407(2) 0.0105(9) Uani 1 d . . . U
C3 C 0.5087(4) -1.1508(15) -0.2086(2) 0.0097(9) Uani 1 d . . . U
O1 O 0.2032(3) -1.3823(11) -0.25217(19) 0.0173(8) Uani 1 d . . . U
H1 H 0.1674 -1.5620 -0.2717 0.021 Uiso 1 d . . R .
N21 N 0.2755(3) -1.5952(13) -0.2043(2) 0.0124(9) Uani 1 d . . . U
H21A H 0.3160 -1.4461 -0.1781 0.015 Uiso 1 d . . R .
H21B H 0.3161 -1.7267 -0.2148 0.015 Uiso 1 d . . R .
H21C H 0.2430 -1.6894 -0.1833 0.015 Uiso 1 d . . R .
O2 O 0.7065(3) -0.6761(12) -0.2506(2) 0.0187(9) Uani 1 d . . . U
H2 H 0.6724 -0.4981 -0.2720 0.022 Uiso 1 d . . R .
N22 N 0.7754(3) -0.4499(13) -0.2035(2) 0.0138(9) Uani 1 d . . . U
H22A H 0.7438 -0.3601 -0.1816 0.017 Uiso 1 d . . R .
H22B H 0.8166 -0.5983 -0.1775 0.017 Uiso 1 d . . R .
H22C H 0.8147 -0.3155 -0.2147 0.017 Uiso 1 d . . R .
O5 O 0.5064(3) -0.6566(12) -0.4102(2) 0.0200(9) Uani 1 d . . . U
H5A H 0.4966 -0.5570 -0.3804 0.024 Uiso 1 d . . R .
H5B H 0.4978 -0.5324 -0.4423 0.024 Uiso 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
Na1 Na1 3.5670(7) 1_545 ?
Na1 Na1 3.5670(7) 1_565 ?
Na1 O6 2.394(5) . ?
Na1 O6 2.360(5) 1_565 ?
Na1 O9 2.955(5) 1_565 ?
Na1 O9 2.497(5) . ?
Na1 N11 2.473(5) . ?
Na1 O7 2.378(6) . ?
O6 Na1 2.360(5) 1_545 ?
O6 H6A 0.8201 . ?
O6 H6B 0.8199 . ?
O9 Na1 2.955(5) 1_545 ?
O9 N19 1.397(5) . ?
N11 N12 1.348(6) . ?
N11 C4 1.347(7) . ?
N12 N13 1.310(6) . ?
N13 H13 0.8599 . ?
N13 N14 1.336(6) . ?
N14 C4 1.349(6) . ?
N15 N16 1.354(6) . ?
N15 C6 1.356(6) . ?
N16 N17 1.318(7) . ?
N17 N18 1.339(6) . ?
N18 C6 1.330(7) . ?
N19 C5 1.292(6) . ?
C4 C5 1.484(7) 1_565 ?
C5 C4 1.484(7) 1_545 ?
C5 C6 1.469(7) . ?
O7 H7A 0.8401 . ?
O7 H7B 0.8401 . ?
Na2 Na2 3.5670(7) 1_545 ?
Na2 Na2 3.5670(7) 1_565 ?
Na2 O3 2.334(5) . ?
Na2 O4 2.382(5) 1_545 ?
Na2 O4 2.371(5) . ?
Na2 H4B 2.6000 . ?
Na2 O8 2.524(5) 1_545 ?
Na2 O8 2.743(5) . ?
Na2 N1 2.439(5) . ?
O3 H3A 0.8400 . ?
O3 H3B 0.8401 . ?
O4 Na2 2.382(5) 1_565 ?
O4 H4A 0.8401 . ?
O4 H4B 0.8399 . ?
O8 Na2 2.524(5) 1_565 ?
O8 N9 1.398(6) . ?
N1 N2 1.345(6) . ?
N1 C1 1.347(7) . ?
N2 N3 1.320(6) . ?
N3 H3 0.8600 . ?
N3 N4 1.345(6) . ?
N4 C1 1.345(6) . ?
N5 N6 1.338(7) . ?
N5 C3 1.345(6) . ?
N6 N7 1.321(6) . ?
N7 N8 1.340(6) . ?
N8 C3 1.334(7) . ?
N9 C2 1.299(6) . ?
C1 C2 1.478(7) 1_545 ?
C2 C1 1.478(7) 1_565 ?
C2 C3 1.472(7) . ?
O1 H1 0.8400 . ?
O1 N21 1.417(6) . ?
N21 H21A 0.8501 . ?
N21 H21B 0.8500 . ?
N21 H21C 0.8502 . ?
O2 H2 0.8399 . ?
O2 N22 1.414(6) . ?
N22 H22A 0.8501 . ?
N22 H22B 0.8500 . ?
N22 H22C 0.8499 . ?
O5 H5A 0.8201 . ?
O5 H5B 0.8199 . ?

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
Na1 Na1 Na1 179.997(1) 1_545 1_565 ?
O6 Na1 Na1 41.75(12) 1_565 1_565 ?
O6 Na1 Na1 41.03(12) . 1_545 ?
O6 Na1 Na1 138.25(12) 1_565 1_545 ?
O6 Na1 Na1 138.97(12) . 1_565 ?
O6 Na1 O6 97.22(16) 1_565 . ?
O6 Na1 O9 123.15(18) 1_565 . ?
O6 Na1 O9 71.55(15) . . ?
O6 Na1 O9 63.99(15) 1_565 1_565 ?
O6 Na1 O9 130.03(16) . 1_565 ?
O6 Na1 N11 163.10(19) . . ?
O6 Na1 N11 99.58(18) 1_565 . ?
O6 Na1 O7 101.0(2) 1_565 . ?
O9 Na1 Na1 43.79(9) 1_565 1_565 ?
O9 Na1 Na1 136.21(9) 1_565 1_545 ?
O9 Na1 Na1 125.05(12) . 1_565 ?
O9 Na1 Na1 54.95(12) . 1_545 ?
O9 Na1 O9 81.26(13) . 1_565 ?
N11 Na1 Na1 57.85(13) . 1_565 ?
N11 Na1 Na1 122.15(13) . 1_545 ?
N11 Na1 O9 97.43(17) . . ?
N11 Na1 O9 57.78(14) . 1_565 ?
O7 Na1 Na1 77.1(2) . 1_545 ?
O7 Na1 Na1 102.9(2) . 1_565 ?
O7 Na1 O6 81.7(2) . . ?
O7 Na1 O9 144.5(3) . 1_565 ?
O7 Na1 O9 130.0(3) . . ?
O7 Na1 N11 96.9(2) . . ?
Na1 O6 Na1 97.22(16) 1_545 . ?
Na1 O6 H6A 101.5 . . ?
Na1 O6 H6A 129.1 1_545 . ?
Na1 O6 H6B 89.0 1_545 . ?
Na1 O6 H6B 124.3 . . ?
H6A O6 H6B 116.6 . . ?
Na1 O9 Na1 81.26(13) . 1_545 ?
N19 O9 Na1 130.6(3) . 1_545 ?
N19 O9 Na1 125.4(3) . . ?
N12 N11 Na1 112.3(3) . . ?
C4 N11 Na1 141.6(3) . . ?
C4 N11 N12 105.0(4) . . ?
N13 N12 N11 108.7(4) . . ?
N12 N13 H13 124.6 . . ?
N12 N13 N14 111.1(4) . . ?
N14 N13 H13 124.4 . . ?
N13 N14 C4 104.1(4) . . ?
N16 N15 C6 104.2(4) . . ?
N17 N16 N15 109.9(4) . . ?
N16 N17 N18 108.7(4) . . ?
C6 N18 N17 106.4(4) . . ?
C5 N19 O9 113.0(4) . . ?
N11 C4 N14 111.1(4) . . ?
N11 C4 C5 126.8(4) . 1_565 ?
N14 C4 C5 122.0(5) . 1_565 ?
N19 C5 C4 125.4(5) . 1_545 ?
N19 C5 C6 115.2(4) . . ?
C6 C5 C4 119.4(4) . 1_545 ?
N15 C6 C5 124.4(5) . . ?
N18 C6 N15 110.7(4) . . ?
N18 C6 C5 124.9(5) . . ?
Na1 O7 H7A 109.4 . . ?
Na1 O7 H7B 109.3 . . ?
H7A O7 H7B 109.4 . . ?
Na2 Na2 Na2 179.998(1) 1_565 1_545 ?
Na2 Na2 H4B 53.4 1_565 . ?
Na2 Na2 H4B 126.6 1_545 . ?
O3 Na2 Na2 92.20(14) . 1_545 ?
O3 Na2 Na2 87.79(14) . 1_565 ?
O3 Na2 O4 98.85(18) . 1_545 ?
O3 Na2 O4 95.54(17) . . ?
O3 Na2 H4B 112.7 . . ?
O3 Na2 O8 90.07(16) . 1_545 ?
O3 Na2 O8 87.20(16) . . ?
O3 Na2 N1 156.09(19) . . ?
O4 Na2 Na2 138.74(12) 1_545 1_565 ?
O4 Na2 Na2 138.51(12) . 1_545 ?
O4 Na2 Na2 41.49(12) . 1_565 ?
O4 Na2 Na2 41.26(12) 1_545 1_545 ?
O4 Na2 O4 97.25(17) . 1_545 ?
O4 Na2 H4B 87.1 1_545 . ?
O4 Na2 H4B 18.7 . . ?
O4 Na2 O8 172.80(16) 1_545 . ?
O4 Na2 O8 85.99(16) . . ?
O4 Na2 O8 169.26(17) . 1_545 ?
O4 Na2 O8 90.90(17) 1_545 1_545 ?
O4 Na2 N1 107.77(17) . . ?
O4 Na2 N1 83.71(17) 1_545 . ?
O8 Na2 Na2 50.01(12) 1_545 1_545 ?
O8 Na2 Na2 135.16(10) . 1_545 ?
O8 Na2 Na2 129.99(12) 1_545 1_565 ?
O8 Na2 Na2 44.84(10) . 1_565 ?
O8 Na2 H4B 94.2 . . ?
O8 Na2 H4B 157.1 1_545 . ?
O8 Na2 O8 85.15(14) 1_545 . ?
N1 Na2 Na2 106.03(13) . 1_565 ?
N1 Na2 Na2 73.97(13) . 1_545 ?
N1 Na2 H4B 91.1 . . ?
N1 Na2 O8 89.18(16) . . ?
N1 Na2 O8 66.06(15) . 1_545 ?
Na2 O3 H3A 116.1 . . ?
Na2 O3 H3B 107.7 . . ?
H3A O3 H3B 113.0 . . ?
Na2 O4 Na2 97.25(17) . 1_565 ?
Na2 O4 H4A 103.1 1_565 . ?
Na2 O4 H4A 104.7 . . ?
Na2 O4 H4B 96.2 . . ?
Na2 O4 H4B 120.9 1_565 . ?
H4A O4 H4B 128.1 . . ?
Na2 O8 Na2 85.15(14) 1_565 . ?
N9 O8 Na2 120.8(3) . . ?
N9 O8 Na2 137.4(3) . 1_565 ?
N2 N1 Na2 118.4(3) . . ?
N2 N1 C1 105.5(4) . . ?
C1 N1 Na2 135.5(3) . . ?
N3 N2 N1 107.9(4) . . ?
N2 N3 H3 124.2 . . ?
N2 N3 N4 111.4(4) . . ?
N4 N3 H3 124.4 . . ?
C1 N4 N3 103.5(4) . . ?
N6 N5 C3 105.1(4) . . ?
N7 N6 N5 109.3(4) . . ?
N6 N7 N8 109.4(4) . . ?
C3 N8 N7 105.2(4) . . ?
C2 N9 O8 114.5(4) . . ?
N1 C1 C2 125.5(4) . 1_545 ?
N4 C1 N1 111.6(4) . . ?
N4 C1 C2 122.8(5) . 1_545 ?
N9 C2 C1 126.4(5) . 1_565 ?
N9 C2 C3 115.6(4) . . ?
C3 C2 C1 118.0(4) . 1_565 ?
N5 C3 C2 125.7(5) . . ?
N8 C3 N5 111.0(5) . . ?
N8 C3 C2 123.3(4) . . ?
N21 O1 H1 97.5 . . ?
O1 N21 H21A 108.9 . . ?
O1 N21 H21B 118.1 . . ?
O1 N21 H21C 103.7 . . ?
H21A N21 H21B 99.9 . . ?
H21A N21 H21C 103.6 . . ?
H21B N21 H21C 121.2 . . ?
N22 O2 H2 96.0 . . ?
O2 N22 H22A 106.0 . . ?
O2 N22 H22B 106.6 . . ?
O2 N22 H22C 117.2 . . ?
H22A N22 H22B 102.6 . . ?
H22A N22 H22C 121.5 . . ?
H22B N22 H22C 100.7 . . ?
H5A O5 H5B 118.6 . . ?

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
Na1 Na1 O6 Na1 180.0 1_565 . . 1_545 ?
Na1 Na1 O9 Na1 180.0 1_565 . . 1_545 ?
Na1 Na1 O9 N19 -45.6(4) 1_565 . . . ?
Na1 Na1 O9 N19 134.4(4) 1_545 . . . ?
Na1 Na1 N11 N12 -108.9(4) 1_565 . . . ?
Na1 Na1 N11 N12 71.1(4) 1_545 . . . ?
Na1 Na1 N11 C4 86.2(6) 1_565 . . . ?
Na1 Na1 N11 C4 -93.8(6) 1_545 . . . ?
Na1 O9 N19 C5 -61.6(6) . . . . ?
Na1 O9 N19 C5 49.8(6) 1_545 . . . ?
Na1 N11 N12 N13 -170.4(3) . . . . ?
Na1 N11 C4 N14 165.3(4) . . . . ?
Na1 N11 C4 C5 -13.4(9) . . . 1_565 ?
O6 Na1 O6 Na1 180.0 1_565 . . 1_545 ?
O6 Na1 O9 Na1 129.07(17) 1_565 . . 1_545 ?
O6 Na1 O9 Na1 42.50(14) . . . 1_545 ?
O6 Na1 O9 N19 -96.6(4) 1_565 . . . ?
O6 Na1 O9 N19 176.9(4) . . . . ?
O6 Na1 N11 N12 76.1(8) . . . . ?
O6 Na1 N11 N12 -110.3(4) 1_565 . . . ?
O6 Na1 N11 C4 -88.9(9) . . . . ?
O6 Na1 N11 C4 84.7(6) 1_565 . . . ?
O9 Na1 O6 Na1 -118.09(18) 1_565 . . 1_545 ?
O9 Na1 O6 Na1 -57.40(18) . . . 1_545 ?
O9 Na1 O9 Na1 180.0 1_565 . . 1_545 ?
O9 Na1 O9 N19 -45.6(4) 1_565 . . . ?
O9 Na1 N11 N12 124.1(4) . . . . ?
O9 Na1 N11 N12 -161.2(4) 1_565 . . . ?
O9 Na1 N11 C4 33.9(6) 1_565 . . . ?
O9 Na1 N11 C4 -40.8(6) . . . . ?
O9 N19 C5 C4 -1.3(8) . . . 1_545 ?
O9 N19 C5 C6 178.1(4) . . . . ?
N11 Na1 O6 Na1 -6.4(8) . . . 1_545 ?
N11 Na1 O9 Na1 -124.33(14) . . . 1_545 ?
N11 Na1 O9 N19 10.0(4) . . . . ?
N11 N12 N13 N14 0.4(6) . . . . ?
N12 N11 C4 N14 -0.3(6) . . . . ?
N12 N11 C4 C5 -178.9(5) . . . 1_565 ?
N12 N13 N14 C4 -0.6(6) . . . . ?
N13 N14 C4 N11 0.6(6) . . . . ?
N13 N14 C4 C5 179.2(5) . . . 1_565 ?
N15 N16 N17 N18 0.4(6) . . . . ?
N16 N15 C6 N18 0.2(6) . . . . ?
N16 N15 C6 C5 -178.9(5) . . . . ?
N16 N17 N18 C6 -0.3(6) . . . . ?
N17 N18 C6 N15 0.1(6) . . . . ?
N17 N18 C6 C5 179.1(5) . . . . ?
N19 C5 C6 N15 162.4(5) . . . . ?
N19 C5 C6 N18 -16.5(8) . . . . ?
C4 N11 N12 N13 0.0(6) . . . . ?
C4 C5 C6 N15 -18.1(8) 1_545 . . . ?
C4 C5 C6 N18 162.9(5) 1_545 . . . ?
C6 N15 N16 N17 -0.3(6) . . . . ?
O7 Na1 O6 Na1 79.9(3) . . . 1_545 ?
O7 Na1 O9 Na1 -18.8(3) . . . 1_545 ?
O7 Na1 O9 N19 115.5(4) . . . . ?
O7 Na1 N11 N12 -7.9(4) . . . . ?
O7 Na1 N11 C4 -172.8(6) . . . . ?
Na2 Na2 O4 Na2 179.997(1) 1_545 . . 1_565 ?
Na2 Na2 O8 Na2 180.0 1_545 . . 1_565 ?
Na2 Na2 O8 N9 -144.1(4) 1_565 . . . ?
Na2 Na2 O8 N9 35.9(4) 1_545 . . . ?
Na2 Na2 N1 N2 -74.8(4) 1_565 . . . ?
Na2 Na2 N1 N2 105.2(4) 1_545 . . . ?
Na2 Na2 N1 C1 114.9(5) 1_565 . . . ?
Na2 Na2 N1 C1 -65.1(5) 1_545 . . . ?
Na2 O8 N9 C2 -45.4(7) 1_565 . . . ?
Na2 O8 N9 C2 74.9(5) . . . . ?
Na2 N1 N2 N3 -171.6(3) . . . . ?
Na2 N1 C1 N4 170.4(4) . . . . ?
Na2 N1 C1 C2 -9.5(9) . . . 1_545 ?
O3 Na2 O4 Na2 80.32(19) . . . 1_565 ?
O3 Na2 O8 Na2 -89.69(16) . . . 1_565 ?
O3 Na2 O8 N9 126.2(4) . . . . ?
O3 Na2 N1 N2 161.9(5) . . . . ?
O3 Na2 N1 C1 -8.4(9) . . . . ?
O4 Na2 O4 Na2 180.0 1_545 . . 1_565 ?
O4 Na2 O8 Na2 6.07(15) . . . 1_565 ?
O4 Na2 O8 Na2 123.1(13) 1_545 . . 1_565 ?
O4 Na2 O8 N9 -138.0(3) . . . . ?
O4 Na2 O8 N9 -21.0(15) 1_545 . . . ?
O4 Na2 N1 N2 -31.4(4) . . . . ?
O4 Na2 N1 N2 64.3(4) 1_545 . . . ?
O4 Na2 N1 C1 158.4(5) . . . . ?
O4 Na2 N1 C1 -106.0(5) 1_545 . . . ?
O8 Na2 O4 Na2 -40.9(10) 1_545 . . 1_565 ?
O8 Na2 O4 Na2 -6.47(16) . . . 1_565 ?
O8 Na2 O8 Na2 180.0 1_545 . . 1_565 ?
O8 Na2 O8 N9 35.9(4) 1_545 . . . ?
O8 Na2 N1 N2 158.1(4) 1_545 . . . ?
O8 Na2 N1 N2 -116.9(4) . . . . ?
O8 Na2 N1 C1 72.8(5) . . . . ?
O8 Na2 N1 C1 -12.2(5) 1_545 . . . ?
O8 N9 C2 C1 2.5(8) . . . 1_565 ?
O8 N9 C2 C3 -178.9(4) . . . . ?
N1 Na2 O4 Na2 -94.31(19) . . . 1_565 ?
N1 Na2 O8 Na2 113.96(14) . . . 1_565 ?
N1 Na2 O8 N9 -30.2(4) . . . . ?
N1 N2 N3 N4 -1.6(6) . . . . ?
N2 N1 C1 N4 -0.7(6) . . . . ?
N2 N1 C1 C2 179.4(5) . . . 1_545 ?
N2 N3 N4 C1 1.1(6) . . . . ?
N3 N4 C1 N1 -0.2(6) . . . . ?
N3 N4 C1 C2 179.7(5) . . . 1_545 ?
N5 N6 N7 N8 -0.1(6) . . . . ?
N6 N5 C3 N8 -0.6(6) . . . . ?
N6 N5 C3 C2 177.9(5) . . . . ?
N6 N7 N8 C3 -0.2(6) . . . . ?
N7 N8 C3 N5 0.5(6) . . . . ?
N7 N8 C3 C2 -178.0(5) . . . . ?
N9 C2 C3 N5 -162.5(5) . . . . ?
N9 C2 C3 N8 15.8(8) . . . . ?
C1 N1 N2 N3 1.4(6) . . . . ?
C1 C2 C3 N5 16.1(8) 1_565 . . . ?
C1 C2 C3 N8 -165.5(5) 1_565 . . . ?
C3 N5 N6 N7 0.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bwn16178a
_database_code_depnum_ccdc_archive 'CCDC 1483891'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-15 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 H9 N10 Na O4'
_chemical_formula_weight         272.19

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'
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   Pca2(1)

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

_cell_length_a                   14.507(3)
_cell_length_b                   3.5938(7)
_cell_length_c                   20.191(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1052.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3234
_cell_measurement_theta_min      1.4037
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7173
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3810
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1232
_reflns_number_gt                1205
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0350P)²+0.4450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(5)
_refine_ls_number_reflns         1232
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
Na1 Na 0.59606(8) 0.0597(3) 0.64975(6) 0.0197(3) Uani 1 1 d . . .
O1 O 0.54272(14) 0.5429(6) 0.56415(10) 0.0178(4) Uani 1 1 d . . .
H1 H 0.4852 0.5153 0.5633 0.021 Uiso 1 1 d R . .
O2 O 0.44884(16) 0.0065(8) 0.68817(13) 0.0298(6) Uani 1 1 d . . .
H2A H 0.4249 0.1255 0.7195 0.036 Uiso 1 1 d R . .
H2B H 0.4018 -0.0745 0.6686 0.036 Uiso 1 1 d R . .
O3 O 0.62521(15) 0.5583(6) 0.72409(11) 0.0223(5) Uani 1 1 d . . .
H3A H 0.6745 0.5280 0.7452 0.027 Uiso 1 1 d R . .
H3B H 0.5833 0.6475 0.7480 0.027 Uiso 1 1 d R . .
N1 N 0.71821(15) 0.3170(7) 0.58267(12) 0.0157(5) Uani 1 1 d . . .
N2 N 0.80567(16) 0.3055(7) 0.60377(12) 0.0168(5) Uani 1 1 d . . .
N3 N 0.85937(16) 0.4627(7) 0.55952(13) 0.0157(5) Uani 1 1 d . . .
N4 N 0.80985(15) 0.5810(7) 0.50767(13) 0.0136(5) Uani 1 1 d . . .
N5 N 0.73777(16) 0.4998(7) 0.37641(12) 0.0157(5) Uani 1 1 d . . .
N6 N 0.72231(17) 0.5812(7) 0.31180(13) 0.0180(5) Uani 1 1 d . . .
N7 N 0.64029(16) 0.7330(7) 0.30539(13) 0.0170(5) Uani 1 1 d . . .
N8 N 0.60036(15) 0.7565(7) 0.36537(13) 0.0161(5) Uani 1 1 d . . .
N9 N 0.55822(16) 0.5828(7) 0.49647(11) 0.0142(5) Uani 1 1 d . . .
C1 C 0.72240(17) 0.4876(8) 0.52315(14) 0.0119(5) Uani 1 1 d . . .
C2 C 0.64385(19) 0.5612(8) 0.47957(15) 0.0134(5) Uani 1 1 d . . .
C3 C 0.66124(18) 0.6103(8) 0.40758(14) 0.0133(5) Uani 1 1 d . . .
O4 O 0.44238(14) 0.1296(6) 0.36647(11) 0.0196(4) Uani 1 1 d . . .
H4 H 0.4939 0.0244 0.3698 0.024 Uiso 1 1 d R . .
N10 N 0.39808(16) -0.0839(7) 0.41553(12) 0.0147(5) Uani 1 1 d . . .
H10A H 0.4400 -0.2215 0.4354 0.018 Uiso 1 1 d R . .
H10B H 0.3728 0.0777 0.4428 0.018 Uiso 1 1 d R . .
H10C H 0.3521 -0.2323 0.4051 0.018 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
Na1 O2 2.280(3) . ?
Na1 O3 2.375(3) . ?
Na1 O3 2.383(2) 1_545 ?
Na1 N1 2.415(3) . ?
Na1 O1 2.570(2) . ?
Na1 O1 2.652(3) 1_545 ?
Na1 Na1 3.5938(7) 1_545 ?
Na1 Na1 3.5938(7) 1_565 ?
O1 N9 1.392(3) . ?
O1 Na1 2.652(2) 1_565 ?
O1 H1 0.8401 . ?
O2 H2A 0.8399 . ?
O2 H2B 0.8399 . ?
O3 Na1 2.383(2) 1_565 ?
O3 H3A 0.8401 . ?
O3 H3B 0.8401 . ?
N1 N2 1.339(3) . ?
N1 C1 1.350(4) . ?
N2 N3 1.313(3) . ?
N3 N4 1.339(4) . ?
N4 C1 1.349(3) . ?
N5 C3 1.337(4) . ?
N5 N6 1.356(4) . ?
N6 N7 1.315(3) . ?
N7 N8 1.345(3) . ?
N8 C3 1.335(4) . ?
N9 C2 1.291(4) . ?
C1 C2 1.464(4) . ?
C2 C3 1.486(4) . ?
O4 N10 1.408(3) . ?
O4 H4 0.8401 . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 H10C 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Na1 O3 90.86(9) . . ?
O2 Na1 O3 83.60(10) . 1_545 ?
O3 Na1 O3 98.09(9) . 1_545 ?
O2 Na1 N1 155.55(11) . . ?
O3 Na1 N1 86.26(9) . . ?
O3 Na1 N1 120.84(9) 1_545 . ?
O2 Na1 O1 90.20(9) . . ?
O3 Na1 O1 88.21(8) . . ?
O3 Na1 O1 171.20(9) 1_545 . ?
N1 Na1 O1 65.47(8) . . ?
O2 Na1 O1 83.67(8) . 1_545 ?
O3 Na1 O1 172.69(9) . 1_545 ?
O3 Na1 O1 86.15(8) 1_545 1_545 ?
N1 Na1 O1 96.71(9) . 1_545 ?
O1 Na1 O1 86.96(7) . 1_545 ?
O2 Na1 Na1 85.19(7) . 1_545 ?
O3 Na1 Na1 138.97(6) . 1_545 ?
O3 Na1 Na1 40.87(6) 1_545 1_545 ?
N1 Na1 Na1 112.52(7) . 1_545 ?
O1 Na1 Na1 132.52(6) . 1_545 ?
O1 Na1 Na1 45.56(5) 1_545 1_545 ?
O2 Na1 Na1 94.81(7) . 1_565 ?
O3 Na1 Na1 41.03(6) . 1_565 ?
O3 Na1 Na1 139.13(6) 1_545 1_565 ?
N1 Na1 Na1 67.48(7) . 1_565 ?
O1 Na1 Na1 47.48(6) . 1_565 ?
O1 Na1 Na1 134.44(5) 1_545 1_565 ?
Na1 Na1 Na1 180.0 1_545 1_565 ?
N9 O1 Na1 132.94(16) . . ?
N9 O1 Na1 121.36(17) . 1_565 ?
Na1 O1 Na1 86.96(7) . 1_565 ?
N9 O1 H1 98.8 . . ?
Na1 O1 H1 103.5 . . ?
Na1 O1 H1 112.7 1_565 . ?
Na1 O2 H2A 127.0 . . ?
Na1 O2 H2B 129.0 . . ?
H2A O2 H2B 101.2 . . ?
Na1 O3 Na1 98.09(9) . 1_565 ?
Na1 O3 H3A 112.0 . . ?
Na1 O3 H3A 124.7 1_565 . ?
Na1 O3 H3B 121.5 . . ?
Na1 O3 H3B 86.9 1_565 . ?
H3A O3 H3B 111.9 . . ?
N2 N1 C1 104.7(2) . . ?
N2 N1 Na1 120.34(18) . . ?
C1 N1 Na1 134.91(18) . . ?
N3 N2 N1 109.4(2) . . ?
N2 N3 N4 110.5(2) . . ?
N3 N4 C1 104.1(2) . . ?
C3 N5 N6 104.6(2) . . ?
N7 N6 N5 109.5(2) . . ?
N6 N7 N8 109.1(2) . . ?
C3 N8 N7 105.4(2) . . ?
C2 N9 O1 114.1(2) . . ?
N4 C1 N1 111.2(2) . . ?
N4 C1 C2 123.2(3) . . ?
N1 C1 C2 125.6(2) . . ?
N9 C2 C1 127.0(3) . . ?
N9 C2 C3 114.5(3) . . ?
C1 C2 C3 118.5(2) . . ?
N8 C3 N5 111.5(2) . . ?
N8 C3 C2 124.0(2) . . ?
N5 C3 C2 124.5(3) . . ?
N10 O4 H4 96.0 . . ?
O4 N10 H10A 108.1 . . ?
O4 N10 H10B 105.7 . . ?
H10A N10 H10B 112.0 . . ?
O4 N10 H10C 120.6 . . ?
H10A N10 H10C 107.0 . . ?
H10B N10 H10C 103.5 . . ?

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
O2 Na1 O1 N9 -132.2(2) . . . . ?
O3 Na1 O1 N9 137.0(2) . . . . ?
O3 Na1 O1 N9 -87.1(6) 1_545 . . . ?
N1 Na1 O1 N9 50.3(2) . . . . ?
O1 Na1 O1 N9 -48.5(2) 1_545 . . . ?
Na1 Na1 O1 N9 -48.5(2) 1_545 . . . ?
Na1 Na1 O1 N9 131.5(2) 1_565 . . . ?
O2 Na1 O1 Na1 96.35(8) . . . 1_565 ?
O3 Na1 O1 Na1 5.49(8) . . . 1_565 ?
O3 Na1 O1 Na1 141.4(6) 1_545 . . 1_565 ?
N1 Na1 O1 Na1 -81.21(9) . . . 1_565 ?
O1 Na1 O1 Na1 180.0 1_545 . . 1_565 ?
Na1 Na1 O1 Na1 180.0 1_545 . . 1_565 ?
O2 Na1 O3 Na1 -96.34(11) . . . 1_565 ?
O3 Na1 O3 Na1 180.0 1_545 . . 1_565 ?
N1 Na1 O3 Na1 59.36(9) . . . 1_565 ?
O1 Na1 O3 Na1 -6.17(10) . . . 1_565 ?
O1 Na1 O3 Na1 -54.9(7) 1_545 . . 1_565 ?
Na1 Na1 O3 Na1 180.000(1) 1_545 . . 1_565 ?
O2 Na1 N1 N2 152.5(2) . . . . ?
O3 Na1 N1 N2 68.6(2) . . . . ?
O3 Na1 N1 N2 -28.6(3) 1_545 . . . ?
O1 Na1 N1 N2 158.4(2) . . . . ?
O1 Na1 N1 N2 -118.1(2) 1_545 . . . ?
Na1 Na1 N1 N2 -73.7(2) 1_545 . . . ?
Na1 Na1 N1 N2 106.3(2) 1_565 . . . ?
O2 Na1 N1 C1 -27.6(4) . . . . ?
O3 Na1 N1 C1 -111.4(3) . . . . ?
O3 Na1 N1 C1 151.4(3) 1_545 . . . ?
O1 Na1 N1 C1 -21.7(3) . . . . ?
O1 Na1 N1 C1 61.9(3) 1_545 . . . ?
Na1 Na1 N1 C1 106.3(3) 1_545 . . . ?
Na1 Na1 N1 C1 -73.7(3) 1_565 . . . ?
C1 N1 N2 N3 0.4(3) . . . . ?
Na1 N1 N2 N3 -179.68(19) . . . . ?
N1 N2 N3 N4 -0.4(3) . . . . ?
N2 N3 N4 C1 0.2(3) . . . . ?
C3 N5 N6 N7 0.0(3) . . . . ?
N5 N6 N7 N8 0.3(3) . . . . ?
N6 N7 N8 C3 -0.5(3) . . . . ?
Na1 O1 N9 C2 -49.8(3) . . . . ?
Na1 O1 N9 C2 69.0(3) 1_565 . . . ?
N3 N4 C1 N1 0.0(3) . . . . ?
N3 N4 C1 C2 -179.3(3) . . . . ?
N2 N1 C1 N4 -0.2(3) . . . . ?
Na1 N1 C1 N4 179.8(2) . . . . ?
N2 N1 C1 C2 179.0(3) . . . . ?
Na1 N1 C1 C2 -0.9(4) . . . . ?
O1 N9 C2 C1 2.4(4) . . . . ?
O1 N9 C2 C3 -178.9(2) . . . . ?
N4 C1 C2 N9 -158.5(3) . . . . ?
N1 C1 C2 N9 22.3(5) . . . . ?
N4 C1 C2 C3 22.9(4) . . . . ?
N1 C1 C2 C3 -156.3(3) . . . . ?
N7 N8 C3 N5 0.5(3) . . . . ?
N7 N8 C3 C2 -176.8(3) . . . . ?
N6 N5 C3 N8 -0.4(3) . . . . ?
N6 N5 C3 C2 176.9(3) . . . . ?
N9 C2 C3 N8 16.5(4) . . . . ?
C1 C2 C3 N8 -164.8(3) . . . . ?
N9 C2 C3 N5 -160.5(3) . . . . ?
C1 C2 C3 N5 18.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 0.84 1.83 2.662(3) 170.7 4_465
O2 H2A N7 0.84 2.04 2.855(4) 163.8 2_665
O2 H2B N2 0.84 2.09 2.911(3) 167.4 4_455
O2 H2B N3 0.84 2.68 3.358(3) 138.9 4_455
O3 H3A N6 0.84 2.02 2.835(3) 163.0 3_655
O3 H3B O4 0.84 2.55 3.238(3) 139.9 2_665
O3 H3B O2 0.84 2.63 3.109(3) 117.3 1_565
O4 H4 N8 0.84 1.82 2.655(3) 171.0 1_545
N10 H10A N9 0.88 2.23 3.083(3) 164.1 1_545
N10 H10B N4 0.88 2.01 2.892(3) 176.1 4_465
N10 H10C N5 0.88 2.00 2.875(3) 171.2 4_455

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.052
