# 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_HFDNTz
_chemical_name_systematic               '5-(fluorodinitromethyl)-2H-tetrazole'
_chemical_name_common                   'HFDNTz'
_chemical_formula_moiety                'C2 H F N6 O4'
_chemical_formula_sum                   'C2 H F N6 O4'
_chemical_formula_iupac                 ?
_chemical_formula_weight                192.09

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'C 1 2/c 1'
_space_group_name_Hall                  '-C 2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'

_cell_length_a                          28.8030(7)
_cell_length_b                          5.37030(10)
_cell_length_c                          28.8969(10)
_cell_angle_alpha                       90
_cell_angle_beta                        119.723(2)
_cell_angle_gamma                       90
_cell_volume                            3881.71(19)
_cell_formula_units_Z                   24
_cell_measurement_reflns_used           7127
_cell_measurement_theta_min             2.8124
_cell_measurement_theta_max             28.9367
_cell_measurement_temperature           100.(2)

_exptl_crystal_description              needle
_exptl_crystal_colour                   'clear colourless'
_exptl_crystal_size_max                 0.435
_exptl_crystal_size_mid                 0.059
_exptl_crystal_size_min                 0.022
_exptl_crystal_density_diffrn           1.972
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    2304

_exptl_absorpt_coefficient_mu           0.200
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'Bruker SADABS V2014/4'
_exptl_absorpt_correction_T_min         0.80
_exptl_absorpt_correction_T_max         1.00

_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        8.3333

_diffrn_reflns_number                   46406
_diffrn_reflns_av_R_equivalents         0.0774
_diffrn_reflns_av_unetI/netI            0.0471
_diffrn_reflns_theta_min                1.62
_diffrn_reflns_theta_max                30.56
_diffrn_reflns_theta_full               30.56
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full    0.998
_diffrn_reflns_limit_h_min              -40
_diffrn_reflns_limit_h_max              40
_diffrn_reflns_limit_k_min              -7
_diffrn_reflns_limit_k_max              7
_diffrn_reflns_limit_l_min              -41
_diffrn_reflns_limit_l_max              41

_refine_special_details                 
;
;

_reflns_number_total                    5932
_reflns_number_gt                       4146
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0760
_refine_ls_R_factor_gt                  0.0414
_refine_ls_wR_factor_gt                 0.0830
_refine_ls_wR_factor_ref                0.0940
_refine_ls_goodness_of_fit_ref          1.035
_refine_ls_restrained_S_all             1.035
_refine_ls_number_reflns                5932
_refine_ls_number_parameters            361
_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)+(0.0348P)²+4.5858P] 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                0.456
_refine_diff_density_min                -0.324
_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 0.41234(6) 0.2864(3) 0.57465(7) 0.0121(3) Uani d . . . 1 . .
    C C2 0.41056(6) 0.2305(3) 0.52329(7) 0.0127(3) Uani d . . . 1 . .
    C C3 0.41128(6) 0.3749(3) 0.33780(6) 0.0122(3) Uani d . . . 1 . .
    C C4 0.36142(6) 0.4249(3) 0.33980(7) 0.0121(3) Uani d . . . 1 . .
    C C5 0.17640(6) 0.5410(3) 0.33778(7) 0.0127(3) Uani d . . . 1 . .
    C C6 0.22798(6) 0.5936(3) 0.38742(7) 0.0129(3) Uani d . . . 1 . .
    F F1 0.37321(4) 0.35649(19) 0.48278(4) 0.0170(2) Uani d . . . 1 . .
    F F2 0.35839(4) 0.29651(19) 0.37703(4) 0.0162(2) Uani d . . . 1 . .
    F F3 0.26858(4) 0.46927(19) 0.38982(4) 0.0159(2) Uani d . . . 1 . .
    N N1 0.38892(6) 0.4848(3) 0.58126(6) 0.0153(3) Uani d . . . 1 . .
    N N2 0.39901(6) 0.4479(3) 0.63070(6) 0.0146(3) Uani d . . . 1 . .
    H H2 0.3874(8) 0.551(4) 0.6467(8) 0.018 Uiso d U . . 1 . .
    N N3 0.42621(6) 0.2439(3) 0.65378(6) 0.0154(3) Uani d . . . 1 . .
    N N4 0.43524(5) 0.1361(3) 0.61775(6) 0.0134(3) Uani d . . . 1 . .
    N N5 0.39939(6) -0.0488(3) 0.51041(6) 0.0137(3) Uani d . . . 1 . .
    N N6 0.46433(6) 0.2767(3) 0.52542(6) 0.0147(3) Uani d . . . 1 . .
    N N7 0.44153(6) 0.1773(3) 0.36059(6) 0.0146(3) Uani d . . . 1 . .
    N N8 0.48099(6) 0.2183(3) 0.35030(6) 0.0145(3) Uani d . . . 1 . .
    H H8 0.5088(8) 0.118(4) 0.3612(8) 0.017 Uiso d U . . 1 . .
    N N9 0.47642(6) 0.4233(3) 0.32354(6) 0.0155(3) Uani d . . . 1 . .
    N N10 0.43111(5) 0.5276(3) 0.31476(6) 0.0136(3) Uani d . . . 1 . .
    N N11 0.31011(6) 0.3754(3) 0.28623(6) 0.0142(3) Uani d . . . 1 . .
    N N12 0.35918(5) 0.7041(3) 0.35128(6) 0.0138(3) Uani d . . . 1 . .
    N N13 0.16922(6) 0.3424(3) 0.30786(6) 0.0150(3) Uani d . . . 1 . .
    N N14 0.11986(6) 0.3833(3) 0.26850(6) 0.0150(3) Uani d . . . 1 . .
    H H14 0.1021(8) 0.280(4) 0.2400(8) 0.018 Uiso d U . . 1 . .
    N N15 0.09743(6) 0.5886(3) 0.27299(6) 0.0152(3) Uani d . . . 1 . .
    N N16 0.13361(5) 0.6936(3) 0.31795(6) 0.0138(3) Uani d . . . 1 . .
    N N17 0.24077(5) 0.8731(3) 0.38970(6) 0.0135(3) Uani d . . . 1 . .
    N N18 0.22574(6) 0.5375(3) 0.43854(6) 0.0138(3) Uani d . . . 1 . .
    O O1 0.35335(5) -0.1058(2) 0.48098(5) 0.0194(3) Uani d . . . 1 . .
    O O2 0.43838(5) -0.1857(2) 0.53273(5) 0.0187(3) Uani d . . . 1 . .
    O O3 0.46298(5) 0.2662(3) 0.48284(5) 0.0233(3) Uani d . . . 1 . .
    O O4 0.50279(5) 0.3148(2) 0.56923(5) 0.0193(3) Uani d . . . 1 . .
    O O5 0.31581(5) 0.3436(2) 0.24780(5) 0.0195(3) Uani d . . . 1 . .
    O O6 0.26907(5) 0.3743(3) 0.28804(5) 0.0232(3) Uani d . . . 1 . .
    O O7 0.34284(5) 0.8415(2) 0.31258(5) 0.0190(3) Uani d . . . 1 . .
    O O8 0.37553(5) 0.7585(2) 0.39735(5) 0.0193(3) Uani d . . . 1 . .
    O O9 0.26929(5) 0.9328(2) 0.37200(5) 0.0184(3) Uani d . . . 1 . .
    O O10 0.21908(5) 1.0077(2) 0.40771(5) 0.0185(3) Uani d . . . 1 . .
    O O11 0.18135(5) 0.5161(2) 0.43347(5) 0.0196(3) Uani d . . . 1 . .
    O O12 0.26855(5) 0.5227(3) 0.47907(5) 0.0224(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 . 1.325(2) ?
    C1 N4 . 1.350(2) ?
    C1 C2 . 1.490(2) ?
    C2 F1 . 1.3180(19) ?
    C2 N6 . 1.539(2) ?
    C2 N5 . 1.540(2) ?
    C3 N7 . 1.323(2) ?
    C3 N10 . 1.349(2) ?
    C3 C4 . 1.490(2) ?
    C4 F2 . 1.3168(18) ?
    C4 N12 . 1.543(2) ?
    C4 N11 . 1.544(2) ?
    C5 N13 . 1.323(2) ?
    C5 N16 . 1.349(2) ?
    C5 C6 . 1.494(2) ?
    C6 F3 . 1.3182(18) ?
    C6 N17 . 1.539(2) ?
    C6 N18 . 1.540(2) ?
    N1 N2 . 1.324(2) ?
    N2 N3 . 1.319(2) ?
    N2 H2 . 0.89(2) ?
    N3 N4 . 1.325(2) ?
    N5 O1 . 1.2071(18) ?
    N5 O2 . 1.2245(18) ?
    N6 O3 . 1.2129(18) ?
    N6 O4 . 1.2170(19) ?
    N7 N8 . 1.328(2) ?
    N8 N9 . 1.314(2) ?
    N8 H8 . 0.88(2) ?
    N9 N10 . 1.3244(19) ?
    N11 O6 . 1.2089(18) ?
    N11 O5 . 1.2124(18) ?
    N12 O8 . 1.2074(18) ?
    N12 O7 . 1.2226(18) ?
    N13 N14 . 1.326(2) ?
    N14 N15 . 1.316(2) ?
    N14 H14 . 0.91(2) ?
    N15 N16 . 1.323(2) ?
    N17 O9 . 1.2067(18) ?
    N17 O10 . 1.2274(18) ?
    N18 O12 . 1.2109(18) ?
    N18 O11 . 1.2181(18) ?

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 . . 113.51(15) ?
    N1 C1 C2 . . 122.49(15) ?
    N4 C1 C2 . . 123.92(15) ?
    F1 C2 C1 . . 113.02(13) ?
    F1 C2 N6 . . 108.34(13) ?
    C1 C2 N6 . . 113.00(13) ?
    F1 C2 N5 . . 107.74(13) ?
    C1 C2 N5 . . 109.68(13) ?
    N6 C2 N5 . . 104.60(12) ?
    N7 C3 N10 . . 113.46(14) ?
    N7 C3 C4 . . 122.34(15) ?
    N10 C3 C4 . . 124.15(15) ?
    F2 C4 C3 . . 113.12(14) ?
    F2 C4 N12 . . 107.84(13) ?
    C3 C4 N12 . . 109.11(13) ?
    F2 C4 N11 . . 108.10(13) ?
    C3 C4 N11 . . 113.08(13) ?
    N12 C4 N11 . . 105.18(12) ?
    N13 C5 N16 . . 113.48(15) ?
    N13 C5 C6 . . 122.60(15) ?
    N16 C5 C6 . . 123.87(15) ?
    F3 C6 C5 . . 112.88(14) ?
    F3 C6 N17 . . 107.73(12) ?
    C5 C6 N17 . . 109.19(14) ?
    F3 C6 N18 . . 107.95(13) ?
    C5 C6 N18 . . 112.91(13) ?
    N17 C6 N18 . . 105.83(13) ?
    N2 N1 C1 . . 100.36(14) ?
    N3 N2 N1 . . 115.32(14) ?
    N3 N2 H2 . . 122.7(14) ?
    N1 N2 H2 . . 122.0(14) ?
    N2 N3 N4 . . 105.32(13) ?
    N3 N4 C1 . . 105.48(14) ?
    O1 N5 O2 . . 128.25(15) ?
    O1 N5 C2 . . 116.23(14) ?
    O2 N5 C2 . . 115.48(13) ?
    O3 N6 O4 . . 128.16(15) ?
    O3 N6 C2 . . 115.24(14) ?
    O4 N6 C2 . . 116.59(13) ?
    C3 N7 N8 . . 100.41(13) ?
    N9 N8 N7 . . 115.09(14) ?
    N9 N8 H8 . . 121.8(13) ?
    N7 N8 H8 . . 123.1(13) ?
    N8 N9 N10 . . 105.59(13) ?
    N9 N10 C3 . . 105.45(14) ?
    O6 N11 O5 . . 128.20(15) ?
    O6 N11 C4 . . 115.33(14) ?
    O5 N11 C4 . . 116.47(13) ?
    O8 N12 O7 . . 128.69(15) ?
    O8 N12 C4 . . 115.92(14) ?
    O7 N12 C4 . . 115.33(13) ?
    C5 N13 N14 . . 100.41(14) ?
    N15 N14 N13 . . 115.09(14) ?
    N15 N14 H14 . . 121.1(13) ?
    N13 N14 H14 . . 123.8(13) ?
    N14 N15 N16 . . 105.51(13) ?
    N15 N16 C5 . . 105.51(14) ?
    O9 N17 O10 . . 128.31(15) ?
    O9 N17 C6 . . 116.08(13) ?
    O10 N17 C6 . . 115.56(13) ?
    O12 N18 O11 . . 127.95(15) ?
    O12 N18 C6 . . 115.71(13) ?
    O11 N18 C6 . . 116.33(14) ?





