# 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_NH4FDNTz
_chemical_name_systematic               ?
_chemical_name_common                   'NH4FDNTz'
_chemical_formula_moiety                'C2 F N6 O4, H4 N'
_chemical_formula_sum                   'C2 H4 F N7 O4'
_chemical_formula_iupac                 ?
_chemical_formula_weight                209.12

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'P 1 21/c 1'
_space_group_name_Hall                  '-P 2ybc'
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                          13.9642(7)
_cell_length_b                          8.9672(5)
_cell_length_c                          13.9957(7)
_cell_angle_alpha                       90
_cell_angle_beta                        115.47160(10)
_cell_angle_gamma                       90
_cell_volume                            1582.19(14)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           37464
_cell_measurement_theta_min             1.62
_cell_measurement_theta_max             30.49
_cell_measurement_temperature           101.(2)

_exptl_crystal_description              prism
_exptl_crystal_colour                   'clear yellow'
_exptl_crystal_size_max                 0.440
_exptl_crystal_size_mid                 0.420
_exptl_crystal_size_min                 0.120
_exptl_crystal_density_diffrn           1.756
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    848

_exptl_absorpt_coefficient_mu           0.174
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Bruker SADABS V2014/4'
_exptl_absorpt_correction_T_min         0.93
_exptl_absorpt_correction_T_max         0.98

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             101.(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                   37464
_diffrn_reflns_av_R_equivalents         0.0384
_diffrn_reflns_av_unetI/netI            0.0235
_diffrn_reflns_theta_min                1.62
_diffrn_reflns_theta_max                30.49
_diffrn_reflns_theta_full               30.49
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full    0.990
_diffrn_reflns_limit_h_min              -19
_diffrn_reflns_limit_h_max              19
_diffrn_reflns_limit_k_min              -12
_diffrn_reflns_limit_k_max              12
_diffrn_reflns_limit_l_min              -19
_diffrn_reflns_limit_l_max              19

_refine_special_details                 
;
;

_reflns_number_total                    4778
_reflns_number_gt                       3941
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0441
_refine_ls_R_factor_gt                  0.0329
_refine_ls_wR_factor_gt                 0.0786
_refine_ls_wR_factor_ref                0.0845
_refine_ls_goodness_of_fit_ref          1.026
_refine_ls_restrained_S_all             1.026
_refine_ls_number_reflns                4778
_refine_ls_number_parameters            277
_refine_ls_number_restraints            0
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           refxyz
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0393P)²+0.5930P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          difmap
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.395
_refine_diff_density_min                -0.270
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

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'
    F F 0.0171 0.0103 '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 0.01012(8) 0.84528(11) 0.26261(8) 0.01147(19) Uani d . . . 1 . .
    C C2 0.10443(8) 0.86925(12) 0.36478(8) 0.01166(19) Uani d . . . 1 . .
    C C3 0.45565(8) 0.59293(11) 0.24714(8) 0.01206(19) Uani d . . . 1 . .
    C C4 0.36164(8) 0.57596(12) 0.26877(8) 0.01285(19) Uani d . . . 1 . .
    F F1 0.18988(5) 0.91121(7) 0.35224(5) 0.01561(14) Uani d . . . 1 . .
    F F2 0.31081(5) 0.44813(8) 0.23409(6) 0.02102(15) Uani d . . . 1 . .
    N N1 -0.07605(7) 0.77053(11) 0.25228(7) 0.01367(18) Uani d . . . 1 . .
    N N2 -0.13932(7) 0.77843(11) 0.14802(7) 0.01404(18) Uani d . . . 1 . .
    N N3 -0.09135(7) 0.85491(10) 0.10034(7) 0.01406(18) Uani d . . . 1 . .
    N N4 0.00440(7) 0.89930(10) 0.17137(7) 0.01342(18) Uani d . . . 1 . .
    N N5 0.08778(7) 0.98996(10) 0.43512(7) 0.01314(17) Uani d . . . 1 . .
    N N6 0.13297(7) 0.72909(10) 0.43491(7) 0.01364(17) Uani d . . . 1 . .
    N N7 0.45149(7) 0.56501(11) 0.15162(7) 0.01559(18) Uani d . . . 1 . .
    N N8 0.55055(8) 0.59330(11) 0.16450(8) 0.01730(19) Uani d . . . 1 . .
    N N9 0.60932(7) 0.63596(11) 0.26293(7) 0.01656(19) Uani d . . . 1 . .
    N N10 0.55073(7) 0.63701(11) 0.31809(7) 0.01405(18) Uani d . . . 1 . .
    N N11 0.39102(7) 0.58794(12) 0.38782(7) 0.01641(19) Uani d . . . 1 . .
    N N12 0.27951(8) 0.70063(12) 0.21906(8) 0.0199(2) Uani d . . . 1 . .
    N N13 0.35928(8) 0.16647(11) 0.48813(8) 0.01345(17) Uani d . . . 1 . .
    H H1 0.3941(11) 0.1516(16) 0.4481(11) 0.016 Uiso d U . . 1 . .
    H H2 0.3633(11) 0.0849(17) 0.5238(12) 0.016 Uiso d U . . 1 . .
    H H3 0.2925(12) 0.1902(16) 0.4478(11) 0.016 Uiso d U . . 1 . .
    H H4 0.3886(11) 0.2390(17) 0.5362(11) 0.016 Uiso d U . . 1 . .
    N N14 0.15787(8) 0.40633(11) 0.62437(8) 0.01328(17) Uani d . . . 1 . .
    H H5 0.2283(12) 0.4053(16) 0.6585(11) 0.016 Uiso d U . . 1 . .
    H H6 0.1319(11) 0.4912(17) 0.6310(11) 0.016 Uiso d U . . 1 . .
    H H7 0.1369(11) 0.3855(16) 0.5556(12) 0.016 Uiso d U . . 1 . .
    H H8 0.1292(11) 0.3364(16) 0.6521(11) 0.016 Uiso d U . . 1 . .
    O O1 0.00095(6) 1.04607(9) 0.40338(7) 0.01803(17) Uani d . . . 1 . .
    O O2 0.16641(6) 1.01866(9) 0.51686(6) 0.01818(17) Uani d . . . 1 . .
    O O3 0.07301(6) 0.70054(9) 0.47503(6) 0.01679(16) Uani d . . . 1 . .
    O O4 0.21039(7) 0.65981(11) 0.44324(8) 0.0258(2) Uani d . . . 1 . .
    O O5 0.41499(7) 0.71214(10) 0.42587(7) 0.02151(18) Uani d . . . 1 . .
    O O6 0.38893(7) 0.47339(11) 0.43273(7) 0.0276(2) Uani d . . . 1 . .
    O O7 0.30835(9) 0.81132(12) 0.18964(9) 0.0373(3) Uani d . . . 1 . .
    O O8 0.19270(7) 0.67572(13) 0.21484(8) 0.0342(3) Uani d . . . 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 N1 . 1.3298(13) ?
    C1 N4 . 1.3357(13) ?
    C1 C2 . 1.4850(14) ?
    C2 F1 . 1.3328(11) ?
    C2 N6 . 1.5381(14) ?
    C2 N5 . 1.5466(14) ?
    C3 N10 . 1.3309(13) ?
    C3 N7 . 1.3366(14) ?
    C3 C4 . 1.4764(14) ?
    C4 F2 . 1.3256(12) ?
    C4 N12 . 1.5372(14) ?
    C4 N11 . 1.5389(14) ?
    N1 N2 . 1.3438(12) ?
    N2 N3 . 1.3224(13) ?
    N3 N4 . 1.3383(12) ?
    N5 O1 . 1.2072(12) ?
    N5 O2 . 1.2248(12) ?
    N6 O4 . 1.2083(12) ?
    N6 O3 . 1.2191(12) ?
    N7 N8 . 1.3401(13) ?
    N8 N9 . 1.3211(13) ?
    N9 N10 . 1.3449(13) ?
    N11 O6 . 1.2110(13) ?
    N11 O5 . 1.2177(13) ?
    N12 O7 . 1.2081(15) ?
    N12 O8 . 1.2088(14) ?
    N13 H1 . 0.896(15) ?
    N13 H2 . 0.873(15) ?
    N13 H3 . 0.883(15) ?
    N13 H4 . 0.898(15) ?
    N14 H5 . 0.890(15) ?
    N14 H6 . 0.865(16) ?
    N14 H7 . 0.897(15) ?
    N14 H8 . 0.916(15) ?

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
    N1 C1 N4 . . 113.55(9) ?
    N1 C1 C2 . . 124.33(9) ?
    N4 C1 C2 . . 122.12(9) ?
    F1 C2 C1 . . 112.81(8) ?
    F1 C2 N6 . . 108.29(8) ?
    C1 C2 N6 . . 112.04(8) ?
    F1 C2 N5 . . 105.93(8) ?
    C1 C2 N5 . . 113.60(8) ?
    N6 C2 N5 . . 103.55(8) ?
    N10 C3 N7 . . 113.71(9) ?
    N10 C3 C4 . . 124.57(9) ?
    N7 C3 C4 . . 121.72(9) ?
    F2 C4 C3 . . 113.41(9) ?
    F2 C4 N12 . . 106.58(8) ?
    C3 C4 N12 . . 112.85(9) ?
    F2 C4 N11 . . 107.95(9) ?
    C3 C4 N11 . . 111.61(8) ?
    N12 C4 N11 . . 103.82(8) ?
    C1 N1 N2 . . 103.48(8) ?
    N3 N2 N1 . . 109.64(8) ?
    N2 N3 N4 . . 109.91(8) ?
    C1 N4 N3 . . 103.42(8) ?
    O1 N5 O2 . . 127.67(10) ?
    O1 N5 C2 . . 117.37(8) ?
    O2 N5 C2 . . 114.95(9) ?
    O4 N6 O3 . . 127.66(10) ?
    O4 N6 C2 . . 117.20(9) ?
    O3 N6 C2 . . 115.14(8) ?
    C3 N7 N8 . . 103.40(9) ?
    N9 N8 N7 . . 109.72(9) ?
    N8 N9 N10 . . 110.01(9) ?
    C3 N10 N9 . . 103.16(9) ?
    O6 N11 O5 . . 127.76(10) ?
    O6 N11 C4 . . 116.61(10) ?
    O5 N11 C4 . . 115.62(9) ?
    O7 N12 O8 . . 127.55(11) ?
    O7 N12 C4 . . 117.30(10) ?
    O8 N12 C4 . . 115.15(11) ?
    H1 N13 H2 . . 108.3(13) ?
    H1 N13 H3 . . 110.0(13) ?
    H2 N13 H3 . . 111.0(13) ?
    H1 N13 H4 . . 112.5(13) ?
    H2 N13 H4 . . 106.4(13) ?
    H3 N13 H4 . . 108.7(13) ?
    H5 N14 H6 . . 111.6(13) ?
    H5 N14 H7 . . 110.4(13) ?
    H6 N14 H7 . . 109.9(13) ?
    H5 N14 H8 . . 110.4(13) ?
    H6 N14 H8 . . 106.1(13) ?
    H7 N14 H8 . . 108.2(12) ?





