# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1554405'
_audit_update_record             
;
2017-06-06 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2017-04-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H10 N Na O7 S'
_chemical_formula_sum            'C9 H10 N Na O7 S'
_chemical_formula_weight         299.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Na H C O S P N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0311 0.0180 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8364(2)
_cell_length_b                   11.9343(4)
_cell_length_c                   27.7283(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2262.29(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3067
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.3560
_cell_measurement_theta_min      6.3690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4359
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         6.385
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00   4.00   1.00    5.00    --  -42.45  38.00  90.00   69
  2  ω    -97.00 -39.00   1.00    5.00    --  -42.45   0.00-150.00   58
  3  ω      3.00  29.00   1.00    5.00    --  -42.45   0.00-150.00   26
  4  ω    118.00 178.00   1.00    5.00    --  106.62 125.00-180.00   60
  5  ω     21.00 138.00   1.00    5.00    --  106.62   0.00-180.00  117
  6  ω     27.00  65.00   1.00    5.00    --  106.62 -94.00 150.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0105843000
_diffrn_orient_matrix_UB_12      0.0458127000
_diffrn_orient_matrix_UB_13      0.0518780000
_diffrn_orient_matrix_UB_21      -0.0770075000
_diffrn_orient_matrix_UB_22      0.1126003000
_diffrn_orient_matrix_UB_23      -0.0193845000
_diffrn_orient_matrix_UB_31      -0.2115011000
_diffrn_orient_matrix_UB_32      -0.0433746000
_diffrn_orient_matrix_UB_33      0.0045779000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1869
_reflns_number_total             2002
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.039
_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)+(0.0514P)²+1.2020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0811
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
S1 S 0.92288(5) 0.68545(3) 0.32505(2) 0.01087(14) Uani 1 1 d . . . . .
Na1 Na 0.92987(8) 0.71990(5) 0.21256(2) 0.01281(17) Uani 1 1 d . . . . .
N1 N 0.71074(19) 0.71415(11) 0.42992(4) 0.0107(3) Uani 1 1 d . . . . .
C1 C 0.9737(2) 0.77809(13) 0.37346(6) 0.0124(3) Uani 1 1 d . . . . .
H1A H 1.071770 0.742795 0.394887 0.015 Uiso 1 1 calc R . . . .
H1B H 1.032274 0.847501 0.360290 0.015 Uiso 1 1 calc R . . . .
C2 C 0.7952(2) 0.80909(13) 0.40323(5) 0.0129(3) Uani 1 1 d . . . . .
H2A H 0.832207 0.868363 0.426482 0.015 Uiso 1 1 calc R . . . .
H2B H 0.694092 0.840468 0.381530 0.015 Uiso 1 1 calc R . . . .
C3 C 0.5339(2) 0.66964(13) 0.41402(6) 0.0115(3) Uani 1 1 d . . . . .
C4 C 0.4481(2) 0.57767(13) 0.44316(6) 0.0110(3) Uani 1 1 d . . . . .
C5 C 0.2737(2) 0.52995(13) 0.42936(5) 0.0128(3) Uani 1 1 d . . . . .
H5 H 0.211697 0.553585 0.400438 0.015 Uiso 1 1 calc R . . . .
C6 C 0.5433(2) 0.54187(13) 0.48572(5) 0.0102(3) Uani 1 1 d . . . . .
C7 C 0.7236(2) 0.58825(13) 0.49997(5) 0.0107(3) Uani 1 1 d . . . . .
C8 C 0.1873(2) 0.44633(13) 0.45793(6) 0.0131(3) Uani 1 1 d . . . . .
H8 H 0.066950 0.413465 0.448234 0.016 Uiso 1 1 calc R . . . .
C9 C 0.8135(2) 0.67789(13) 0.47057(5) 0.0117(3) Uani 1 1 d . . . . .
O1 O 1.10408(16) 0.67500(10) 0.29828(4) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.76982(16) 0.73797(10) 0.29646(4) 0.0154(3) Uani 1 1 d . . . . .
O3 O 0.86075(16) 0.57827(9) 0.34623(4) 0.0141(3) Uani 1 1 d . . . . .
O4 O 0.97075(17) 0.71930(10) 0.48064(4) 0.0162(3) Uani 1 1 d . . . . .
O5 O 0.45262(16) 0.70588(10) 0.37819(4) 0.0155(3) Uani 1 1 d . . . . .
O6 O 1.00183(17) 0.51191(11) 0.20455(5) 0.0164(3) Uani 1 1 d . . . . .
O7 O 0.8830(2) 0.91637(10) 0.20337(4) 0.0171(3) Uani 1 1 d . . . . .
H7A H 0.769(4) 0.947(2) 0.2012(9) 0.042(7) Uiso 1 1 d . . . . .
H7B H 0.952(4) 0.954(2) 0.1882(9) 0.028(6) Uiso 1 1 d . . . . .
H6A H 1.109(5) 0.522(3) 0.1882(11) 0.056(8) Uiso 1 1 d . . . . .
H6B H 1.043(4) 0.479(2) 0.2285(10) 0.036(7) 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
S1 Na1 3.1463(7) . ?
S1 C1 1.7734(16) . ?
S1 O1 1.4494(12) . ?
S1 O2 1.4547(12) . ?
S1 O3 1.4702(11) . ?
Na1 Na1 3.9992(7) 6_556 ?
Na1 Na1 3.9992(7) 6_656 ?
Na1 O1 2.7120(13) . ?
Na1 O1 2.3104(12) 6_556 ?
Na1 O2 2.5797(12) . ?
Na1 O2 2.3475(12) 6_656 ?
Na1 O5 2.5268(13) 6_656 ?
Na1 O6 2.5402(14) . ?
Na1 O7 2.3802(14) . ?
N1 C2 1.4715(19) . ?
N1 C3 1.392(2) . ?
N1 C9 1.397(2) . ?
C1 C2 1.519(2) . ?
C3 C4 1.484(2) . ?
C3 O5 1.218(2) . ?
C4 C5 1.375(2) . ?
C4 C6 1.414(2) . ?
C5 C8 1.405(2) . ?
C6 C6 1.406(3) 5_666 ?
C6 C7 1.408(2) . ?
C7 C8 1.380(2) 5_666 ?
C7 C9 1.479(2) . ?
C9 O4 1.216(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 Na1 131.75(5) . . ?
O1 S1 Na1 59.38(5) . . ?
O1 S1 C1 105.89(7) . . ?
O1 S1 O2 111.89(7) . . ?
O1 S1 O3 112.12(7) . . ?
O2 S1 Na1 54.15(5) . . ?
O2 S1 C1 106.54(7) . . ?
O2 S1 O3 112.63(7) . . ?
O3 S1 Na1 120.94(5) . . ?
O3 S1 C1 107.25(7) . . ?
S1 Na1 Na1 58.159(19) . 6_556 ?
S1 Na1 Na1 59.89(2) . 6_656 ?
Na1 Na1 Na1 117.46(3) 6_556 6_656 ?
O1 Na1 S1 27.38(3) . . ?
O1 Na1 S1 94.83(4) 6_556 . ?
O1 Na1 Na1 33.87(3) . 6_656 ?
O1 Na1 Na1 40.86(3) 6_556 6_556 ?
O1 Na1 Na1 153.06(4) 6_556 6_656 ?
O1 Na1 Na1 85.43(3) . 6_556 ?
O1 Na1 O1 119.45(4) 6_556 . ?
O1 Na1 O2 74.21(4) 6_556 . ?
O1 Na1 O2 164.12(5) 6_556 6_656 ?
O1 Na1 O5 85.09(4) 6_556 6_656 ?
O1 Na1 O6 87.06(5) 6_556 . ?
O1 Na1 O7 94.86(5) 6_556 . ?
O2 Na1 S1 97.63(3) 6_656 . ?
O2 Na1 S1 27.20(3) . . ?
O2 Na1 Na1 37.73(3) 6_656 6_656 ?
O2 Na1 Na1 154.36(4) 6_656 6_556 ?
O2 Na1 Na1 33.84(3) . 6_556 ?
O2 Na1 Na1 83.94(3) . 6_656 ?
O2 Na1 O1 54.02(4) . . ?
O2 Na1 O1 71.14(4) 6_656 . ?
O2 Na1 O2 120.55(4) 6_656 . ?
O2 Na1 O5 80.73(4) 6_656 6_656 ?
O2 Na1 O6 83.61(4) 6_656 . ?
O2 Na1 O7 91.79(5) 6_656 . ?
O5 Na1 S1 168.39(4) 6_656 . ?
O5 Na1 Na1 117.67(3) 6_656 6_656 ?
O5 Na1 Na1 124.72(3) 6_656 6_556 ?
O5 Na1 O1 146.38(4) 6_656 . ?
O5 Na1 O2 158.39(4) 6_656 . ?
O5 Na1 O6 80.57(4) 6_656 . ?
O6 Na1 S1 87.82(3) . . ?
O6 Na1 Na1 102.18(3) . 6_556 ?
O6 Na1 Na1 83.10(3) . 6_656 ?
O6 Na1 O1 78.38(4) . . ?
O6 Na1 O2 104.05(4) . . ?
O7 Na1 S1 103.47(4) . . ?
O7 Na1 Na1 86.60(4) . 6_556 ?
O7 Na1 Na1 99.82(4) . 6_656 ?
O7 Na1 O1 110.34(4) . . ?
O7 Na1 O2 87.55(5) . . ?
O7 Na1 O5 88.10(4) . 6_656 ?
O7 Na1 O6 168.31(5) . . ?
C3 N1 C2 118.38(12) . . ?
C3 N1 C9 125.03(13) . . ?
C9 N1 C2 116.56(13) . . ?
C2 C1 S1 113.95(11) . . ?
N1 C2 C1 113.64(12) . . ?
N1 C3 C4 116.94(13) . . ?
O5 C3 N1 121.27(14) . . ?
O5 C3 C4 121.79(15) . . ?
C5 C4 C3 119.82(14) . . ?
C5 C4 C6 120.42(15) . . ?
C6 C4 C3 119.73(14) . . ?
C4 C5 C8 120.13(14) . . ?
C6 C6 C4 119.40(18) 5_666 . ?
C6 C6 C7 119.36(18) 5_666 . ?
C7 C6 C4 121.24(15) . . ?
C6 C7 C9 119.57(14) . . ?
C8 C7 C6 120.43(14) 5_666 . ?
C8 C7 C9 119.95(14) 5_666 . ?
C7 C8 C5 120.24(14) 5_666 . ?
N1 C9 C7 117.40(13) . . ?
O4 C9 N1 120.27(14) . . ?
O4 C9 C7 122.33(14) . . ?
S1 O1 Na1 150.53(7) . 6_656 ?
S1 O1 Na1 93.23(6) . . ?
Na1 O1 Na1 105.27(4) 6_656 . ?
S1 O2 Na1 136.94(7) . 6_556 ?
S1 O2 Na1 98.64(6) . . ?
Na1 O2 Na1 108.43(4) 6_556 . ?
C3 O5 Na1 149.79(10) . 6_556 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.389
_oxdiff_exptl_absorpt_empirical_full_min 0.586
