# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_spnpd
_database_code_depnum_ccdc_archive 'CCDC 1403345'
#Added by publCIF



_audit_update_record             
;
2015-06-01 deposited with the CCDC.
2015-06-17 downloaded from the CCDC.
;
_publcif_datablock.id            {50313768-ab27-4455-9264-2f39138d3d66}
# publcif _publ_body_element loop end
_audit_creation_date             2015-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H8 N Na O5'
_chemical_formula_sum            'C6 H8 N Na O5'
_chemical_formula_weight         197.12
_chemical_absolute_configuration ?
_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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           46
_space_group_name_H-M_alt        'I m a 2'
_space_group_name_Hall           'I 2 -2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   6.8849(6)
_cell_length_b                   19.6618(16)
_cell_length_c                   6.4413(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     871.95(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2595
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.302
_diffrn_reflns_theta_min         3.328
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.794
_reflns_number_gt                1065
_reflns_number_total             1087
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 444 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(17)
_refine_ls_extinction_coef       0.46(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1087
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.1360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0727
_refine_special_details          ?
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.2500 -0.72843(5) -0.70789(15) 0.0272(3) Uani 1 2 d S T P . .
C5 C -0.2500 -0.52558(12) -0.3716(5) 0.0325(6) Uani 1 2 d S T P . .
O1 O -0.2500 -0.32175(8) -0.2456(2) 0.0262(4) Uani 1 2 d S T P . .
O2 O -0.2500 -0.61470(14) -0.5989(5) 0.0643(8) Uani 1 2 d S T P . .
N1 N -0.2500 -0.59717(11) -0.4151(5) 0.0419(6) Uani 1 2 d S T P . .
C3 C -0.2500 -0.43553(15) -0.1264(4) 0.0401(7) Uani 1 2 d S T P . .
H3 H -0.2500 -0.4209 0.0110 0.048 Uiso 1 2 calc RS T P . .
C2 C -0.2500 -0.38695(11) -0.2853(4) 0.0229(5) Uani 1 2 d S T P . .
O3 O -0.2500 -0.63814(10) -0.2730(5) 0.0563(8) Uani 1 2 d S T P . .
C1 C -0.2500 -0.41089(15) -0.4911(4) 0.0404(7) Uani 1 2 d S T P . .
H1 H -0.2500 -0.3800 -0.6004 0.048 Uiso 1 2 calc RS T P . .
C6 C -0.2500 -0.47980(16) -0.5326(5) 0.0462(8) Uani 1 2 d S T P . .
H6 H -0.2500 -0.4952 -0.6692 0.055 Uiso 1 2 calc RS T P . .
C4 C -0.2500 -0.50445(14) -0.1674(4) 0.0389(7) Uani 1 2 d S T P . .
H4 H -0.2500 -0.5360 -0.0597 0.047 Uiso 1 2 calc RS T P . .
O4 O -0.00692(18) -0.73635(7) -0.96268(19) 0.0301(3) Uani 1 1 d . . . . .
H4A H 0.057(4) -0.7114(14) -1.029(4) 0.034(6) Uiso 1 1 d . . . . .
H4B H 0.065(5) -0.7659(16) -0.915(5) 0.061(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 Na1 3.3305(5) 6_434 ?
Na1 Na1 3.3305(5) 6_435 ?
Na1 O2 2.344(3) . ?
Na1 O3 2.657(2) 6_434 ?
Na1 O4 2.3491(14) . ?
Na1 O4 2.4032(14) 6_435 ?
Na1 O4 2.4032(14) 8_435 ?
Na1 O4 2.3491(14) 3_455 ?
C5 N1 1.435(3) . ?
C5 C6 1.373(4) . ?
C5 C4 1.379(4) . ?
O1 C2 1.307(2) . ?
O2 N1 1.233(4) . ?
N1 O3 1.219(4) . ?
C3 C2 1.400(4) . ?
C3 C4 1.381(4) . ?
C2 C1 1.407(3) . ?
O3 Na1 2.657(2) 6_435 ?
C1 C6 1.381(4) . ?
O4 Na1 2.4032(14) 6_434 ?

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 150.49(6) 6_435 6_434 ?
O2 Na1 Na1 87.32(9) . 6_435 ?
O2 Na1 Na1 122.19(9) . 6_434 ?
O2 Na1 O3 171.64(12) . 6_434 ?
O2 Na1 O4 105.82(7) . 3_455 ?
O2 Na1 O4 105.82(7) . . ?
O2 Na1 O4 94.48(7) . 8_435 ?
O2 Na1 O4 94.48(7) . 6_435 ?
O3 Na1 Na1 84.32(8) 6_434 6_435 ?
O3 Na1 Na1 66.17(8) 6_434 6_434 ?
O4 Na1 Na1 124.21(4) 6_435 6_434 ?
O4 Na1 Na1 46.17(3) . 6_434 ?
O4 Na1 Na1 131.20(4) 3_455 6_435 ?
O4 Na1 Na1 131.20(4) . 6_435 ?
O4 Na1 Na1 124.21(4) 8_435 6_434 ?
O4 Na1 Na1 46.17(3) 3_455 6_434 ?
O4 Na1 Na1 44.85(3) 6_435 6_435 ?
O4 Na1 Na1 44.85(3) 8_435 6_435 ?
O4 Na1 O3 79.88(6) 3_455 6_434 ?
O4 Na1 O3 79.88(6) . 6_434 ?
O4 Na1 O3 79.58(7) 6_435 6_434 ?
O4 Na1 O3 79.58(7) 8_435 6_434 ?
O4 Na1 O4 86.79(4) 3_455 6_435 ?
O4 Na1 O4 88.28(7) 8_435 6_435 ?
O4 Na1 O4 159.42(4) . 6_435 ?
O4 Na1 O4 90.86(7) 3_455 . ?
O4 Na1 O4 86.79(4) . 8_435 ?
O4 Na1 O4 159.42(4) 3_455 8_435 ?
C6 C5 N1 119.7(3) . . ?
C6 C5 C4 121.5(2) . . ?
C4 C5 N1 118.8(3) . . ?
N1 O2 Na1 123.7(2) . . ?
O2 N1 C5 117.5(3) . . ?
O3 N1 C5 120.1(3) . . ?
O3 N1 O2 122.4(3) . . ?
C4 C3 C2 122.0(3) . . ?
O1 C2 C3 121.8(2) . . ?
O1 C2 C1 120.8(2) . . ?
C3 C2 C1 117.4(2) . . ?
N1 O3 Na1 140.4(2) . 6_435 ?
C6 C1 C2 120.7(2) . . ?
C5 C6 C1 119.8(2) . . ?
C5 C4 C3 118.6(2) . . ?
Na1 O4 Na1 88.98(4) . 6_434 ?


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
