# 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 2019

####################################################################### 
# 
# 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_20190416ZH_NLG_ZZW1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1912224'
loop_
_audit_author_name
_audit_author_address
'wangying Zhu'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-08-29 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H9 N11 O2'
_chemical_formula_weight         267.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.9841(4)
_cell_length_b                   10.3283(6)
_cell_length_c                   15.0301(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.578(2)
_cell_angle_gamma                90
_cell_volume                     1080.72(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    6768
_cell_measurement_theta_min      3.72
_cell_measurement_theta_max      53.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.719
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      253(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8035
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.137
_diffrn_reflns_theta_max         53.940
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             1911
_reflns_number_gt                1787
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.9463P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1911
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4552(3) 0.40247(17) 0.74196(12) 0.0263(4) Uani 1 1 d . . . . .
C2 C 0.3893(2) 0.45232(17) 0.65515(11) 0.0251(4) Uani 1 1 d . . . . .
C3 C 0.3285(2) 0.62923(17) 0.54967(11) 0.0244(4) Uani 1 1 d . . . . .
C4 C 0.2126(3) 0.75746(17) 0.40736(12) 0.0278(4) Uani 1 1 d . . . . .
C5 C 0.1087(3) 0.58578(18) 0.33377(12) 0.0275(4) Uani 1 1 d . . . . .
C6 C 0.1413(4) 0.1435(2) 0.44354(17) 0.0489(6) Uani 1 1 d . . . . .
H6A H 0.270928 0.136327 0.425241 0.073 Uiso 1 1 calc R U . . .
H6B H 0.052690 0.100849 0.400000 0.073 Uiso 1 1 calc R U . . .
H6C H 0.134605 0.102769 0.501351 0.073 Uiso 1 1 calc R U . . .
N1 N 0.4305(2) 0.27745(15) 0.74148(10) 0.0324(4) Uani 1 1 d . . . . .
N2 N 0.3267(2) 0.35738(15) 0.60422(10) 0.0320(4) Uani 1 1 d . . . . .
N3 N 0.5344(3) 0.46997(16) 0.81208(10) 0.0385(4) Uani 1 1 d . . . . .
H3A H 0.573095 0.430039 0.861235 0.046 Uiso 1 1 calc R U . . .
H3B H 0.547058 0.553541 0.808272 0.046 Uiso 1 1 calc R U . . .
N4 N 0.3961(2) 0.57969(14) 0.63043(10) 0.0272(4) Uani 1 1 d . . . . .
H4 H 0.448030 0.633864 0.669593 0.033 Uiso 1 1 calc R U . . .
N5 N 0.3555(2) 0.76381(15) 0.54683(10) 0.0291(4) Uani 1 1 d . . . . .
N6 N 0.2530(2) 0.55331(14) 0.48709(9) 0.0249(4) Uani 1 1 d . . . . .
N7 N 0.1935(2) 0.62465(14) 0.41296(9) 0.0247(3) Uani 1 1 d . . . . .
N8 N 0.2970(2) 0.82639(15) 0.47500(10) 0.0315(4) Uani 1 1 d . . . . .
N9 N 0.1424(3) 0.79807(16) 0.32812(11) 0.0359(4) Uani 1 1 d . . . . .
N10 N 0.0772(3) 0.69096(16) 0.28178(11) 0.0351(4) Uani 1 1 d . . . . .
N11 N 0.0679(3) 0.46364(16) 0.31233(11) 0.0388(4) Uani 1 1 d . . . . .
H11A H 0.014927 0.444920 0.259550 0.047 Uiso 1 1 calc R U . . .
H11B H 0.094226 0.402297 0.351061 0.047 Uiso 1 1 calc R U . . .
O1 O 0.3497(2) 0.24642(12) 0.65648(9) 0.0360(4) Uani 1 1 d . . . . .
O2 O 0.0912(2) 0.27550(14) 0.44942(10) 0.0461(4) Uani 1 1 d . . . . .
H2 H 0.165520 0.311658 0.487500 0.069 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.303(2) . ?
C1 N3 1.345(2) . ?
C1 C2 1.443(2) . ?
C2 N2 1.298(2) . ?
C2 N4 1.369(2) . ?
C3 N6 1.303(2) . ?
C3 N4 1.366(2) . ?
C3 N5 1.404(2) . ?
C4 N9 1.320(2) . ?
C4 N8 1.339(2) . ?
C4 N7 1.381(2) . ?
C5 N11 1.327(2) . ?
C5 N10 1.346(2) . ?
C5 N7 1.348(2) . ?
C6 O2 1.411(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
N1 O1 1.392(2) . ?
N2 O1 1.391(2) . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N4 H4 0.8700 . ?
N5 N8 1.296(2) . ?
N6 N7 1.372(2) . ?
N9 N10 1.366(2) . ?
N11 H11A 0.8700 . ?
N11 H11B 0.8700 . ?
O2 H2 0.8300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N3 124.33(16) . . ?
N1 C1 C2 108.43(16) . . ?
N3 C1 C2 127.22(16) . . ?
N2 C2 N4 125.67(16) . . ?
N2 C2 C1 109.37(16) . . ?
N4 C2 C1 124.94(16) . . ?
N6 C3 N4 120.47(16) . . ?
N6 C3 N5 128.42(16) . . ?
N4 C3 N5 111.10(14) . . ?
N9 C4 N8 128.73(17) . . ?
N9 C4 N7 109.87(16) . . ?
N8 C4 N7 121.37(16) . . ?
N11 C5 N10 127.18(17) . . ?
N11 C5 N7 124.62(17) . . ?
N10 C5 N7 108.19(16) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 N1 O1 106.08(14) . . ?
C2 N2 O1 105.72(14) . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C3 N4 C2 125.73(15) . . ?
C3 N4 H4 117.1 . . ?
C2 N4 H4 117.1 . . ?
N8 N5 C3 118.99(15) . . ?
C3 N6 N7 109.99(14) . . ?
C5 N7 N6 129.82(15) . . ?
C5 N7 C4 106.25(15) . . ?
N6 N7 C4 123.93(14) . . ?
N5 N8 C4 117.25(15) . . ?
C4 N9 N10 106.70(15) . . ?
C5 N10 N9 108.99(15) . . ?
C5 N11 H11A 120.0 . . ?
C5 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
N1 O1 N2 110.40(12) . . ?
C6 O2 H2 109.5 . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_20190425ZH_NLG_ZHU_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1915957'
loop_
_audit_author_name
_audit_author_address
'wangying Zhu'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-08-29 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H11 Cl0 N13 Na2 O10'
_chemical_formula_weight         459.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1104 0.0938 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.3798(4)
_cell_length_b                   9.9018(7)
_cell_length_c                   26.2299(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1657.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4221
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      54.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.236
_shelx_estimated_absorpt_T_min   0.799
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3072
_exptl_absorpt_correction_T_max  0.6407
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11470
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         54.138
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3022
_reflns_number_gt                2450
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.987

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0702P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3022
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.7138(3) 0.8025(2) 0.27104(7) 0.0259(5) Uani 1 1 d . . . . .
C1 C 0.6924(6) 0.1634(6) 0.56409(17) 0.0185(11) Uani 1 1 d . . . . .
C2 C 0.7174(6) 0.2496(5) 0.52044(17) 0.0173(11) Uani 1 1 d . . . . .
C3 C 0.6866(6) 0.4758(6) 0.48507(17) 0.0192(11) Uani 1 1 d . . . . .
C4 C 0.5934(6) 0.6704(6) 0.42292(17) 0.0183(11) Uani 1 1 d . . . . .
C5 C 0.6207(6) 0.5470(6) 0.35471(17) 0.0189(11) Uani 1 1 d . . . . .
N1 N 0.6433(6) 0.1425(5) 0.65051(15) 0.0218(10) Uani 1 1 d . . . . .
N2 N 0.6682(6) 0.2228(5) 0.61072(14) 0.0207(10) Uani 1 1 d . . . . .
N3 N 0.6921(5) 0.0376(5) 0.54842(15) 0.0203(9) Uani 1 1 d . . . . .
N4 N 0.7308(6) 0.1779(5) 0.47882(15) 0.0206(9) Uani 1 1 d . . . . .
N5 N 0.7205(6) 0.3876(4) 0.52399(16) 0.0202(9) Uani 1 1 d . . . . .
H5 H 0.756643 0.435552 0.556752 0.024 Uiso 1 1 d R U . . .
N6 N 0.6853(5) 0.4367(5) 0.43749(14) 0.0180(9) Uani 1 1 d . . . . .
N7 N 0.6520(6) 0.6075(5) 0.50397(15) 0.0217(10) Uani 1 1 d . . . . .
N8 N 0.6033(6) 0.7028(5) 0.47301(15) 0.0248(10) Uani 1 1 d . . . . .
N9 N 0.6365(5) 0.5422(5) 0.40641(14) 0.0177(9) Uani 1 1 d . . . . .
N10 N 0.5491(6) 0.7496(5) 0.38421(16) 0.0240(10) Uani 1 1 d . . . . .
N11 N 0.5674(6) 0.6735(5) 0.34124(15) 0.0236(10) Uani 1 1 d . . . . .
N12 N 0.6316(6) 0.4305(5) 0.32766(14) 0.0204(9) Uani 1 1 d . . . . .
N13 N 0.6693(5) 0.4424(5) 0.27887(15) 0.0214(9) Uani 1 1 d . . . . .
Na2 Na 0.5384(3) 0.4355(2) 0.67348(8) 0.0281(5) Uani 1 1 d . . . . .
O1 O 0.6423(5) 0.0174(4) 0.64773(13) 0.0272(8) Uani 1 1 d . . . . .
O2 O 0.6167(5) 0.2025(4) 0.69271(13) 0.0279(9) Uani 1 1 d . . . . .
O3 O 0.7165(5) 0.0437(4) 0.49561(12) 0.0237(8) Uani 1 1 d . . . . .
O4 O 0.7255(5) 0.5483(4) 0.25731(13) 0.0285(9) Uani 1 1 d . . . . .
O5 O 0.6454(5) 0.3334(4) 0.25281(12) 0.0238(8) Uani 1 1 d . . . . .
O1W O 0.2085(5) 0.3426(4) 0.63352(13) 0.0274(8) Uani 1 1 d . . . . .
H1WA H 0.194268 0.243865 0.645727 0.033 Uiso 1 1 d R U . . .
H1WB H 0.210668 0.323264 0.599427 0.033 Uiso 1 1 d R U . . .
O2W O 0.9629(5) 0.2175(4) 0.08996(14) 0.0308(9) Uani 1 1 d . . . . .
H2WA H 0.919888 0.260729 0.065651 0.037 Uiso 1 1 d R U . . .
H2WB H 0.901388 0.149329 0.083151 0.037 Uiso 1 1 d R U . . .
O3W O 0.2768(5) 0.4559(4) 0.74334(13) 0.0278(8) Uani 1 1 d . . . . .
H3WA H 0.314904 0.450834 0.775567 0.033 Uiso 1 1 d R U . . .
H3WB H 0.259105 0.373434 0.736467 0.033 Uiso 1 1 d R U . . .
O4W O 1.0183(5) 0.8247(4) 0.31694(13) 0.0277(9) Uani 1 1 d . . . . .
H4WA H 1.101271 0.819372 0.295004 0.033 Uiso 1 1 d R U . . .
H4WB H 1.054670 0.777272 0.347604 0.033 Uiso 1 1 d R U . . .
O5W O 0.8359(5) 0.4954(4) 0.61939(13) 0.0255(8) Uani 1 1 d . . . . .
H5WA H 0.880484 0.572138 0.612947 0.031 Uiso 1 1 d R U . . .
H5WB H 0.942184 0.435038 0.629547 0.031 Uiso 1 1 d R U . . .


_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 O4W 2.296(4) . ?
Na1 O2 2.322(4) 2_664 ?
Na1 O5 2.396(4) 3_655 ?
Na1 N11 2.428(5) . ?
Na1 O3W 2.455(5) 4_566 ?
Na1 O4 2.544(5) . ?
Na1 Na2 3.625(3) 4_566 ?
Na1 Na2 3.821(3) 2_664 ?
Na1 H4WA 2.5559 . ?
C1 N3 1.312(7) . ?
C1 N2 1.365(6) . ?
C1 C2 1.437(6) . ?
C2 N4 1.305(6) . ?
C2 N5 1.370(7) . ?
C3 N6 1.307(6) . ?
C3 N5 1.361(6) . ?
C3 N7 1.413(7) . ?
C4 N10 1.314(6) . ?
C4 N8 1.354(6) . ?
C4 N9 1.370(7) . ?
C5 N11 1.345(7) . ?
C5 N12 1.357(7) . ?
C5 N9 1.361(5) . ?
N1 O1 1.241(5) . ?
N1 O2 1.267(5) . ?
N1 N2 1.321(6) . ?
N1 Na2 3.037(5) . ?
N2 Na2 2.799(5) . ?
N3 O3 1.395(5) . ?
N4 O3 1.403(6) . ?
N5 H5 1.0086 . ?
N6 N9 1.361(6) . ?
N7 N8 1.283(6) . ?
N10 N11 1.361(6) . ?
N12 N13 1.307(5) . ?
N13 O4 1.243(6) . ?
N13 O5 1.287(6) . ?
Na2 O4W 2.391(5) 4_466 ?
Na2 O2 2.413(5) . ?
Na2 O5W 2.443(4) . ?
Na2 O3W 2.486(4) . ?
Na2 O1W 2.524(4) . ?
Na2 O4 2.671(4) 2_665 ?
Na2 H3WB 2.5061 . ?
O1W H1WA 1.0332 . ?
O1W H1WB 0.9147 . ?
O2W H2WA 0.8156 . ?
O2W H2WB 0.8011 . ?
O3W H3WA 0.8809 . ?
O3W H3WB 0.8435 . ?
O4W H4WA 0.7835 . ?
O4W H4WB 0.9601 . ?
O5W H5WA 0.8284 . ?
O5W H5WB 0.9426 . ?

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
O4W Na1 O2 94.14(13) . 2_664 ?
O4W Na1 O5 159.09(16) . 3_655 ?
O2 Na1 O5 102.54(13) 2_664 3_655 ?
O4W Na1 N11 88.75(14) . . ?
O2 Na1 N11 147.03(19) 2_664 . ?
O5 Na1 N11 84.10(13) 3_655 . ?
O4W Na1 O3W 81.29(14) . 4_566 ?
O2 Na1 O3W 78.97(14) 2_664 4_566 ?
O5 Na1 O3W 89.54(14) 3_655 4_566 ?
N11 Na1 O3W 133.80(17) . 4_566 ?
O4W Na1 O4 98.31(15) . . ?
O2 Na1 O4 80.80(15) 2_664 . ?
O5 Na1 O4 96.74(15) 3_655 . ?
N11 Na1 O4 66.30(14) . . ?
O3W Na1 O4 159.68(14) 4_566 . ?
O4W Na1 Na2 40.31(11) . 4_566 ?
O2 Na1 Na2 96.00(12) 2_664 4_566 ?
O5 Na1 Na2 124.05(13) 3_655 4_566 ?
N11 Na1 Na2 106.97(12) . 4_566 ?
O3W Na1 Na2 43.16(9) 4_566 4_566 ?
O4 Na1 Na2 138.47(11) . 4_566 ?
O4W Na1 Na2 93.46(11) . 2_664 ?
O2 Na1 Na2 37.03(11) 2_664 2_664 ?
O5 Na1 Na2 107.45(11) 3_655 2_664 ?
N11 Na1 Na2 110.05(14) . 2_664 ?
O3W Na1 Na2 115.49(10) 4_566 2_664 ?
O4 Na1 Na2 44.19(9) . 2_664 ?
Na2 Na1 Na2 118.30(5) 4_566 2_664 ?
O4W Na1 H4WA 17.6 . . ?
O2 Na1 H4WA 76.6 2_664 . ?
O5 Na1 H4WA 168.9 3_655 . ?
N11 Na1 H4WA 102.7 . . ?
O3W Na1 H4WA 79.4 4_566 . ?
O4 Na1 H4WA 94.1 . . ?
Na2 Na1 H4WA 45.7 4_566 . ?
Na2 Na1 H4WA 78.8 2_664 . ?
N3 C1 N2 133.5(5) . . ?
N3 C1 C2 108.3(4) . . ?
N2 C1 C2 118.1(5) . . ?
N4 C2 N5 126.8(4) . . ?
N4 C2 C1 110.6(5) . . ?
N5 C2 C1 122.7(4) . . ?
N6 C3 N5 121.8(5) . . ?
N6 C3 N7 127.4(5) . . ?
N5 C3 N7 110.7(4) . . ?
N10 C4 N8 128.2(5) . . ?
N10 C4 N9 110.6(4) . . ?
N8 C4 N9 121.1(5) . . ?
N11 C5 N12 131.9(4) . . ?
N11 C5 N9 108.3(5) . . ?
N12 C5 N9 119.2(5) . . ?
O1 N1 O2 121.2(4) . . ?
O1 N1 N2 123.7(4) . . ?
O2 N1 N2 115.1(4) . . ?
O1 N1 Na2 164.6(3) . . ?
O2 N1 Na2 49.4(2) . . ?
N2 N1 Na2 67.0(3) . . ?
N1 N2 C1 117.5(4) . . ?
N1 N2 Na2 87.3(3) . . ?
C1 N2 Na2 152.1(3) . . ?
C1 N3 O3 105.6(4) . . ?
C2 N4 O3 104.4(4) . . ?
C3 N5 C2 125.9(4) . . ?
C3 N5 H5 111.9 . . ?
C2 N5 H5 122.1 . . ?
C3 N6 N9 110.3(4) . . ?
N8 N7 C3 119.6(4) . . ?
N7 N8 C4 116.8(5) . . ?
C5 N9 N6 129.9(4) . . ?
C5 N9 C4 105.5(4) . . ?
N6 N9 C4 124.6(4) . . ?
C4 N10 N11 106.9(4) . . ?
C5 N11 N10 108.7(4) . . ?
C5 N11 Na1 126.3(3) . . ?
N10 N11 Na1 111.7(3) . . ?
N13 N12 C5 116.4(4) . . ?
O4 N13 O5 120.0(4) . . ?
O4 N13 N12 125.1(4) . . ?
O5 N13 N12 115.0(4) . . ?
O4W Na2 O2 159.75(15) 4_466 . ?
O4W Na2 O5W 82.02(14) 4_466 . ?
O2 Na2 O5W 101.12(14) . . ?
O4W Na2 O3W 78.81(14) 4_466 . ?
O2 Na2 O3W 93.59(14) . . ?
O5W Na2 O3W 158.37(16) . . ?
O4W Na2 O1W 111.13(15) 4_466 . ?
O2 Na2 O1W 84.92(14) . . ?
O5W Na2 O1W 119.68(13) . . ?
O3W Na2 O1W 77.06(12) . . ?
O4W Na2 O4 83.32(14) 4_466 2_665 ?
O2 Na2 O4 76.63(13) . 2_665 ?
O5W Na2 O4 91.44(13) . 2_665 ?
O3W Na2 O4 76.52(12) . 2_665 ?
O1W Na2 O4 146.54(14) . 2_665 ?
O4W Na2 N2 145.58(15) 4_466 . ?
O2 Na2 N2 48.88(12) . . ?
O5W Na2 N2 67.12(13) . . ?
O3W Na2 N2 133.90(15) . . ?
O1W Na2 N2 74.26(13) . . ?
O4 Na2 N2 111.27(14) 2_665 . ?
O4W Na2 N1 168.80(14) 4_466 . ?
O2 Na2 N1 23.52(11) . . ?
O5W Na2 N1 86.88(13) . . ?
O3W Na2 N1 111.83(14) . . ?
O1W Na2 N1 75.75(13) . . ?
O4 Na2 N1 95.54(13) 2_665 . ?
N2 Na2 N1 25.76(11) . . ?
O4W Na2 Na1 38.40(9) 4_466 4_466 ?
O2 Na2 Na1 135.94(11) . 4_466 ?
O5W Na2 Na1 120.19(12) . 4_466 ?
O3W Na2 Na1 42.49(10) . 4_466 ?
O1W Na2 Na1 87.19(11) . 4_466 ?
O4 Na2 Na1 87.05(10) 2_665 4_466 ?
N2 Na2 Na1 160.74(11) . 4_466 ?
N1 Na2 Na1 152.79(10) . 4_466 ?
O4W Na2 Na1 124.34(12) 4_466 2_665 ?
O2 Na2 Na1 35.41(9) . 2_665 ?
O5W Na2 Na1 102.56(10) . 2_665 ?
O3W Na2 Na1 80.46(10) . 2_665 ?
O1W Na2 Na1 113.49(12) . 2_665 ?
O4 Na2 Na1 41.61(10) 2_665 2_665 ?
N2 Na2 Na1 78.90(10) . 2_665 ?
N1 Na2 Na1 56.82(9) . 2_665 ?
Na1 Na2 Na1 114.14(5) 4_466 2_665 ?
O4W Na2 H3WB 97.8 4_466 . ?
O2 Na2 H3WB 77.0 . . ?
O5W Na2 H3WB 174.1 . . ?
O3W Na2 H3WB 19.4 . . ?
O1W Na2 H3WB 65.9 . . ?
O4 Na2 H3WB 82.7 2_665 . ?
N2 Na2 H3WB 114.4 . . ?
N1 Na2 H3WB 93.1 . . ?
Na1 Na2 H3WB 60.3 4_466 . ?
Na1 Na2 H3WB 72.6 2_665 . ?
N1 O2 Na1 134.4(3) . 2_665 ?
N1 O2 Na2 107.0(3) . . ?
Na1 O2 Na2 107.56(17) 2_665 . ?
N3 O3 N4 111.1(4) . . ?
N13 O4 Na1 139.6(3) . . ?
N13 O4 Na2 126.0(3) . 2_664 ?
Na1 O4 Na2 94.20(14) . 2_664 ?
N13 O5 Na1 111.0(3) . 3_645 ?
Na2 O1W H1WA 106.8 . . ?
Na2 O1W H1WB 118.0 . . ?
H1WA O1W H1WB 96.1 . . ?
H2WA O2W H2WB 95.9 . . ?
Na1 O3W Na2 94.35(15) 4_466 . ?
Na1 O3W H3WA 104.3 4_466 . ?
Na2 O3W H3WA 121.2 . . ?
Na1 O3W H3WB 152.6 4_466 . ?
Na2 O3W H3WB 81.6 . . ?
H3WA O3W H3WB 100.8 . . ?
Na1 O4W Na2 101.28(16) . 4_566 ?
Na1 O4W H4WA 100.4 . . ?
Na2 O4W H4WA 96.2 4_566 . ?
Na1 O4W H4WB 126.6 . . ?
Na2 O4W H4WB 112.7 4_566 . ?
H4WA O4W H4WB 114.8 . . ?
Na2 O5W H5WA 127.4 . . ?
Na2 O5W H5WB 103.9 . . ?
H5WA O5W H5WB 113.1 . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.086

