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

data_global
_audit_creation_method                  'APEX2 v2014.9-0'

_publ_requested_journal                 ?

_publ_contact_author_name               'Ralf Haiges'
_publ_contact_author_address            
;
University of Southern California
Loker Hydrocarbon Research Institute and Department of Chemistry
Los Angeles, CA 90089
USA
;
_publ_contact_author_email              haiges@usc.edu
_publ_contact_author_fax                ?
_publ_contact_author_phone              '+1 (213) 740-3197'

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_C2H2N3NaO5
_chemical_name_systematic               'sodium dinitrocyanomethide'
_chemical_name_common                   'NaDinitrocyanomethide'
_chemical_formula_moiety                'C2 H2 N3 Na O5'
_chemical_formula_sum                   'C2 H2 N3 Na O5'
_chemical_formula_iupac                 ?
_chemical_formula_weight                171.06
_chemical_absolute_configuration        ?

_chemical_melting_point                 ?

_space_group_crystal_system             orthorhombic
_space_group_name_H-M_alt               'P 21 21 21'
_space_group_name_Hall                  'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x+1/2, -y, z+1/2'

_cell_length_a                          7.5138(6)
_cell_length_b                          8.1663(6)
_cell_length_c                          19.9151(14)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            1221.99(16)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           30172
_cell_measurement_theta_min             2.04
_cell_measurement_theta_max             30.50
_cell_measurement_temperature           100.(2)

_exptl_crystal_description              prism
_exptl_crystal_colour                   'clear yellow'
_exptl_crystal_size_max                 0.700
_exptl_crystal_size_mid                 0.185
_exptl_crystal_size_min                 0.148
_exptl_crystal_density_diffrn           1.860
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    688

_exptl_absorpt_coefficient_mu           0.237
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Bruker SADABS V2014/4'
_exptl_absorpt_correction_T_min         0.85
_exptl_absorpt_correction_T_max         0.97

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             100.(2)

_diffrn_source                          'fine-focus tube'
_diffrn_source_type                     ?

_diffrn_radiation_type                  'MoK\a '
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         'TRIUMPH curved-crystal'

_diffrn_measurement_device_type         'Bruker APEX II CCD'
_diffrn_measurement_method              'omega- and phi-scans'

_diffrn_detector_area_resol_mean        ?

_diffrn_reflns_number                   30172
_diffrn_reflns_av_R_equivalents         0.0355
_diffrn_reflns_av_unetI/netI            0.0194
_diffrn_reflns_theta_min                2.04
_diffrn_reflns_theta_max                30.50
_diffrn_reflns_theta_full               30.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full    0.999
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -11
_diffrn_reflns_limit_k_max              11
_diffrn_reflns_limit_l_min              -28
_diffrn_reflns_limit_l_max              27

_refine_special_details                 
;
;

_reflns_number_total                    3734
_reflns_number_gt                       3551
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0274
_refine_ls_R_factor_gt                  0.0253
_refine_ls_wR_factor_gt                 0.0651
_refine_ls_wR_factor_ref                0.0661
_refine_ls_goodness_of_fit_ref          1.060
_refine_ls_restrained_S_all             1.060
_refine_ls_number_reflns                3734
_refine_ls_number_parameters            201
_refine_ls_number_restraints            0
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0372P)²+0.2231P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          difmap
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.000
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.360
_refine_diff_density_min                -0.306
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?
_refine_ls_abs_structure_details        
;
Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack          0.07(10)

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'

_computing_data_collection              
    'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement              'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_reduction               'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution           'SHELXTL XT 2014/4 (Bruker AXS)'
_computing_structure_refinement         'SHELXTL XL 2014/6 (Bruker AXS)'
_computing_molecular_graphics           ?
_computing_publication_material         'SHELXTL XL 2014/6 (Bruker AXS)'

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.98170(19) 0.38640(17) 0.54451(7) 0.0111(2) Uani d . . . 1 . .
    C C2 0.9879(2) 0.23515(18) 0.57913(7) 0.0142(3) Uani d . . . 1 . .
    C C3 0.0280(2) 0.33654(19) 0.77799(7) 0.0135(3) Uani d . . . 1 . .
    C C4 -0.1286(2) 0.3679(2) 0.74112(8) 0.0169(3) Uani d . . . 1 . .
    N N1 0.81561(17) 0.45014(16) 0.52825(6) 0.0104(2) Uani d . . . 1 . .
    N N2 1.14153(17) 0.46024(16) 0.52758(6) 0.0106(2) Uani d . . . 1 . .
    N N3 0.9936(2) 0.11141(19) 0.60633(8) 0.0254(3) Uani d . . . 1 . .
    N N4 0.19101(18) 0.37860(17) 0.74918(6) 0.0133(2) Uani d . . . 1 . .
    N N5 0.01080(18) 0.28539(15) 0.84422(6) 0.0122(2) Uani d . . . 1 . .
    N N6 -0.2565(2) 0.3917(3) 0.71184(8) 0.0289(4) Uani d . . . 1 . .
    Na Na1 0.47850(9) 0.37895(8) 0.64290(3) 0.01413(13) Uani d . . . 1 . .
    Na Na2 0.47560(8) 0.65522(7) 0.49546(3) 0.01415(13) Uani d . . . 1 . .
    O O1 0.68419(14) 0.37207(15) 0.54956(6) 0.0152(2) Uani d . . . 1 . .
    O O2 0.79752(15) 0.57655(14) 0.49395(6) 0.0147(2) Uani d . . . 1 . .
    O O3 1.28019(14) 0.38769(15) 0.54531(6) 0.0150(2) Uani d . . . 1 . .
    O O4 1.14895(16) 0.59222(14) 0.49632(6) 0.0150(2) Uani d . . . 1 . .
    O O5 0.33501(15) 0.35773(17) 0.77811(6) 0.0197(2) Uani d . . . 1 . .
    O O6 0.18246(17) 0.43980(17) 0.69138(6) 0.0203(3) Uani d . . . 1 . .
    O O7 0.14091(17) 0.25245(17) 0.87974(6) 0.0186(2) Uani d . . . 1 . .
    O O8 -0.14389(16) 0.27725(16) 0.86673(6) 0.0183(2) Uani d . . . 1 . .
    O O1S 0.49294(15) 0.66061(13) 0.61653(5) 0.0151(2) Uani d . . . 1 . .
    H H1S 0.5868 0.7036 0.6369 0.023 Uiso d U . R 1 . .
    H H2S 0.4076 0.6942 0.6326 0.023 Uiso d U . R 1 . .
    O O2S 0.4228(2) 0.10316(17) 0.64656(8) 0.0302(3) Uani d . . . 1 . .
    H H3S 0.3084 0.0859 0.6521 0.045 Uiso d U . R 1 . .
    H H4S 0.4809 0.0589 0.6802 0.045 Uiso d U . R 1 . .


_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N2 . 1.3855(19) ?
    C1 N1 . 1.3904(19) ?
    C1 C2 . 1.415(2) ?
    C2 N3 . 1.147(2) ?
    C3 N5 . 1.3896(18) ?
    C3 N4 . 1.395(2) ?
    C3 C4 . 1.411(2) ?
    C4 N6 . 1.141(2) ?
    N1 O2 . 1.2452(17) ?
    N1 O1 . 1.2497(17) ?
    N2 O4 . 1.2459(17) ?
    N2 O3 . 1.2496(17) ?
    N2 Na2 1_655 3.0406(15) ?
    N3 Na2 2_556 2.9780(18) ?
    N4 O5 . 1.2377(18) ?
    N4 O6 . 1.2565(17) ?
    N4 Na1 . 3.0243(14) ?
    N5 O7 . 1.2362(18) ?
    N5 O8 . 1.2476(18) ?
    N5 Na2 4_565 3.0524(13) ?
    N6 Na1 1_455 2.4207(17) ?
    Na1 O2S . 2.2920(15) ?
    Na1 O1S . 2.3618(13) ?
    Na1 O1 . 2.4180(13) ?
    Na1 N6 1_655 2.4207(17) ?
    Na1 O3 1_455 2.4499(13) ?
    Na1 O6 . 2.4754(14) ?
    Na1 O5 . 2.9059(14) ?
    Na1 H2S . 2.6369 ?
    Na2 O1S . 2.4150(13) ?
    Na2 O4 2_466 2.4448(13) ?
    Na2 O2 . 2.5029(13) ?
    Na2 O4 1_455 2.5078(13) ?
    Na2 O2 2_466 2.5755(13) ?
    Na2 O7 4_564 2.5780(14) ?
    Na2 O3 1_455 2.8133(14) ?
    Na2 O8 4_564 2.9113(14) ?
    Na2 N3 2_456 2.9779(18) ?
    Na2 O1 . 2.9940(14) ?
    Na2 N2 1_455 3.0407(15) ?
    Na2 N5 4_564 3.0524(14) ?
    O2 Na2 2_566 2.5754(13) ?
    O3 Na1 1_655 2.4499(13) ?
    O3 Na2 1_655 2.8134(14) ?
    O4 Na2 2_566 2.4448(13) ?
    O4 Na2 1_655 2.5078(13) ?
    O7 Na2 4_565 2.5780(14) ?
    O8 Na2 4_565 2.9112(13) ?
    O1S H1S . 0.8866 ?
    O1S H2S . 0.7672 ?
    O2S H3S . 0.878 ?
    O2S H4S . 0.8777 ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 C1 N1 . . 123.94(12) ?
    N2 C1 C2 . . 118.02(13) ?
    N1 C1 C2 . . 118.02(13) ?
    N3 C2 C1 . . 178.99(17) ?
    N5 C3 N4 . . 123.10(13) ?
    N5 C3 C4 . . 118.09(14) ?
    N4 C3 C4 . . 118.26(13) ?
    N6 C4 C3 . . 179.0(2) ?
    O2 N1 O1 . . 121.53(13) ?
    O2 N1 C1 . . 122.42(13) ?
    O1 N1 C1 . . 116.05(12) ?
    O4 N2 O3 . . 120.94(13) ?
    O4 N2 C1 . . 122.48(13) ?
    O3 N2 C1 . . 116.59(13) ?
    O4 N2 Na2 . 1_655 53.48(7) ?
    O3 N2 Na2 . 1_655 67.63(8) ?
    C1 N2 Na2 . 1_655 174.10(10) ?
    C2 N3 Na2 . 2_556 108.72(12) ?
    O5 N4 O6 . . 121.73(13) ?
    O5 N4 C3 . . 122.81(13) ?
    O6 N4 C3 . . 115.45(13) ?
    O5 N4 Na1 . . 72.64(8) ?
    O6 N4 Na1 . . 52.77(8) ?
    C3 N4 Na1 . . 156.19(10) ?
    O7 N5 O8 . . 121.30(13) ?
    O7 N5 C3 . . 122.33(13) ?
    O8 N5 C3 . . 116.36(13) ?
    O7 N5 Na2 . 4_565 56.19(7) ?
    O8 N5 Na2 . 4_565 71.64(8) ?
    C3 N5 Na2 . 4_565 152.34(10) ?
    C4 N6 Na1 . 1_455 167.30(18) ?
    O2S Na1 O1S . . 166.52(5) ?
    O2S Na1 O1 . . 96.80(6) ?
    O1S Na1 O1 . . 79.77(4) ?
    O2S Na1 N6 . 1_655 100.04(7) ?
    O1S Na1 N6 . 1_655 92.67(6) ?
    O1 Na1 N6 . 1_655 84.91(5) ?
    O2S Na1 O3 . 1_455 86.72(5) ?
    O1S Na1 O3 . 1_455 79.82(4) ?
    O1 Na1 O3 . 1_455 77.27(4) ?
    N6 Na1 O3 1_655 1_455 161.61(6) ?
    O2S Na1 O6 . . 91.19(6) ?
    O1S Na1 O6 . . 86.13(5) ?
    O1 Na1 O6 . . 151.51(5) ?
    N6 Na1 O6 1_655 . 120.61(6) ?
    O3 Na1 O6 1_455 . 75.94(4) ?
    O2S Na1 O5 . . 81.03(5) ?
    O1S Na1 O5 . . 106.33(4) ?
    O1 Na1 O5 . . 161.47(5) ?
    N6 Na1 O5 1_655 . 77.41(5) ?
    O3 Na1 O5 1_455 . 120.74(4) ?
    O6 Na1 O5 . . 46.93(4) ?
    O2S Na1 N4 . . 81.16(5) ?
    O1S Na1 N4 . . 100.91(4) ?
    O1 Na1 N4 . . 174.00(5) ?
    N6 Na1 N4 1_655 . 100.98(5) ?
    O3 Na1 N4 1_455 . 96.94(4) ?
    O6 Na1 N4 . . 23.84(4) ?
    O5 Na1 N4 . . 23.99(3) ?
    O2S Na1 H2S . . 157.7 ?
    O1S Na1 H2S . . 16.5 ?
    O1 Na1 H2S . . 95.3 ?
    N6 Na1 H2S 1_655 . 99.7 ?
    O3 Na1 H2S 1_455 . 77.7 ?
    O6 Na1 H2S . . 69.7 ?
    O5 Na1 H2S . . 93.2 ?
    N4 Na1 H2S . . 84.9 ?
    O1S Na2 O4 . 2_466 83.63(4) ?
    O1S Na2 O2 . . 87.97(4) ?
    O4 Na2 O2 2_466 . 72.69(4) ?
    O1S Na2 O4 . 1_455 92.85(4) ?
    O4 Na2 O4 2_466 1_455 133.95(4) ?
    O2 Na2 O4 . 1_455 153.29(4) ?
    O1S Na2 O2 . 2_466 86.03(4) ?
    O4 Na2 O2 2_466 2_466 63.50(4) ?
    O2 Na2 O2 . 2_466 136.17(4) ?
    O4 Na2 O2 1_455 2_466 70.45(4) ?
    O1S Na2 O7 . 4_564 154.89(5) ?
    O4 Na2 O7 2_466 4_564 89.66(5) ?
    O2 Na2 O7 . 4_564 113.11(4) ?
    O4 Na2 O7 1_455 4_564 74.56(4) ?
    O2 Na2 O7 2_466 4_564 69.39(4) ?
    O1S Na2 O3 . 1_455 71.94(4) ?
    O4 Na2 O3 2_466 1_455 155.45(5) ?
    O2 Na2 O3 . 1_455 108.01(4) ?
    O4 Na2 O3 1_455 1_455 47.74(4) ?
    O2 Na2 O3 2_466 1_455 111.13(4) ?
    O7 Na2 O3 4_564 1_455 111.43(4) ?
    O1S Na2 O8 . 4_564 148.46(4) ?
    O4 Na2 O8 2_466 4_564 70.60(4) ?
    O2 Na2 O8 . 4_564 67.56(4) ?
    O4 Na2 O8 1_455 4_564 118.03(4) ?
    O2 Na2 O8 2_466 4_564 97.86(4) ?
    O7 Na2 O8 4_564 4_564 45.96(4) ?
    O3 Na2 O8 1_455 4_564 133.20(4) ?
    O1S Na2 N3 . 2_456 133.67(5) ?
    O4 Na2 N3 2_466 2_456 129.66(5) ?
    O2 Na2 N3 . 2_456 76.14(4) ?
    O4 Na2 N3 1_455 2_456 84.20(5) ?
    O2 Na2 N3 2_466 2_456 134.52(5) ?
    O7 Na2 N3 4_564 2_456 67.71(4) ?
    O3 Na2 N3 1_455 2_456 72.30(4) ?
    O8 Na2 N3 4_564 2_456 61.28(4) ?
    O1S Na2 O1 . . 68.07(4) ?
    O4 Na2 O1 2_466 . 110.40(4) ?
    O2 Na2 O1 . . 45.59(4) ?
    O4 Na2 O1 1_455 . 110.57(4) ?
    O2 Na2 O1 2_466 . 154.07(4) ?
    O7 Na2 O1 4_564 . 136.50(4) ?
    O3 Na2 O1 1_455 . 63.03(3) ?
    O8 Na2 O1 4_564 . 103.64(4) ?
    N3 Na2 O1 2_456 . 69.91(4) ?
    O1S Na2 N2 . 1_455 81.03(4) ?
    O4 Na2 N2 2_466 1_455 150.17(5) ?
    O2 Na2 N2 . 1_455 131.75(4) ?
    O4 Na2 N2 1_455 1_455 23.53(4) ?
    O2 Na2 N2 2_466 1_455 89.96(4) ?
    O7 Na2 N2 4_564 1_455 93.49(4) ?
    O3 Na2 N2 1_455 1_455 24.25(3) ?
    O8 Na2 N2 4_564 1_455 130.02(4) ?
    N3 Na2 N2 2_456 1_455 78.33(4) ?
    O1 Na2 N2 . 1_455 87.25(4) ?
    O1S Na2 N5 . 4_564 168.65(4) ?
    O4 Na2 N5 2_466 4_564 85.08(4) ?
    O2 Na2 N5 . 4_564 89.81(4) ?
    O4 Na2 N5 1_455 4_564 94.13(4) ?
    O2 Na2 N5 2_466 4_564 87.88(4) ?
    O7 Na2 N5 4_564 4_564 23.48(4) ?
    O3 Na2 N5 1_455 4_564 119.28(4) ?
    O8 Na2 N5 4_564 4_564 24.00(3) ?
    N3 Na2 N5 2_456 4_564 56.15(4) ?
    O1 Na2 N5 . 4_564 117.41(4) ?
    N2 Na2 N5 1_455 4_564 108.57(4) ?
    N1 O1 Na1 . . 138.96(10) ?
    N1 O1 Na2 . . 84.11(9) ?
    Na1 O1 Na2 . . 85.65(4) ?
    N1 O2 Na2 . . 108.16(9) ?
    N1 O2 Na2 . 2_566 127.11(9) ?
    Na2 O2 Na2 . 2_566 106.43(4) ?
    N2 O3 Na1 . 1_655 138.17(10) ?
    N2 O3 Na2 . 1_655 88.12(9) ?
    Na1 O3 Na2 1_655 1_655 89.15(4) ?
    N2 O4 Na2 . 2_566 132.26(10) ?
    N2 O4 Na2 . 1_655 102.99(9) ?
    Na2 O4 Na2 2_566 1_655 110.41(4) ?
    N4 O5 Na1 . . 83.38(9) ?
    N4 O6 Na1 . . 103.39(10) ?
    N5 O7 Na2 . 4_565 100.33(9) ?
    N5 O8 Na2 . 4_565 84.36(8) ?
    Na1 O1S Na2 . . 101.64(4) ?
    Na1 O1S H1S . . 108.7 ?
    Na2 O1S H1S . . 120.5 ?
    Na1 O1S H2S . . 102.5 ?
    Na2 O1S H2S . . 112.1 ?
    H1S O1S H2S . . 109.4 ?
    Na1 O2S H3S . . 109.9 ?
    Na1 O2S H4S . . 109.8 ?
    H3S O2S H4S . . 109.0 ?





