##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_date_recd_electronic     2008-03-10
_journal_date_accepted     2008-04-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     11
_journal_page_first     m1375
_journal_page_last     m1375
_journal_paper_category     QM
_journal_coeditor_code     NC2095
_publ_contact_author_name     'K. Adil'
_publ_contact_author_address
;
Laboratoire des Oxydes et Fluorures
UMR 6010 CNRS
Faculté des Sciences
Université du Maine
Avenue Olivier Messiaen
72085 Le Mans Cedex 9
France
;
_publ_contact_author_email     karim.adil@univ-lemans.fr
_publ_contact_author_fax     '(33) 2 43 83 35 06'
_publ_contact_author_phone     '(33) 2 43 83 33 52'
_publ_section_title
;
Diethylenetriaminium hexafluoridotitanate(IV) fluoride
;
loop_
    _publ_author_name
    _publ_author_address
    'J. Lhoste'
;
Laboratoire des Oxydes et Fluorures
UMR 6010 CNRS
Faculté des Sciences et Techniques
Université du Maine
Avenue Olivier Messiaen
72085 Le Mans Cedex 9
France
;
    'K. Adil'
;
Laboratoire des Oxydes et Fluorures
UMR 6010 CNRS
Faculté des Sciences et Techniques
Université du Maine
Avenue Olivier Messiaen
72085 Le Mans Cedex 9
France
;
    'M. Leblanc'
;
Laboratoire des Oxydes et Fluorures
UMR 6010 CNRS
Faculté des Sciences et Techniques
Université du Maine
Avenue Olivier Messiaen
72085 Le Mans Cedex 9
France
;
    'V. Maisonneuve'
;
Laboratoire des Oxydes et Fluorures
UMR 6010 CNRS
Faculté des Sciences et Techniques
Université du Maine
Avenue Olivier Messiaen
72085 Le Mans Cedex 9
France
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Diethylenetriaminium hexafluoridotitanate(IV) fluoride
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H21 N4 3+ , F6 Ti 2- , F -'
_chemical_formula_sum     'C6 H21 F7 N4 Ti'
_chemical_formula_iupac     '(C6 H21 N4) [Ti F6] F'
_chemical_formula_weight     330.14
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     16.265(4)
_cell_length_b     8.089(3)
_cell_length_c     21.778(5)
_cell_angle_alpha     90.00
_cell_angle_beta     110.54(2)
_cell_angle_gamma     90.00
_cell_volume     2683.1(13)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     32
_cell_measurement_theta_min     29.1
_cell_measurement_theta_max     30.9
_cell_measurement_temperature     298(2)
_exptl_crystal_description     parallelepiped
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.635
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1360
_exptl_absorpt_coefficient_mu     0.710
_exptl_absorpt_correction_type     Gaussian
_exptl_absorpt_process_details     '(SHELX76; Sheldrick, 2008)'
_exptl_absorpt_correction_T_min     0.850
_exptl_absorpt_correction_T_max     0.929
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens AED2'
_diffrn_measurement_method     2θ/ω
_diffrn_reflns_number     6191
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0714
_diffrn_reflns_theta_min     1.98
_diffrn_reflns_theta_max     27.52
_diffrn_reflns_theta_full     27.52
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     28
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     15
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger.
;
_reflns_number_total     6133
_reflns_number_gt     3531
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1411
_refine_ls_R_factor_gt     0.0611
_refine_ls_wR_factor_gt     0.1313
_refine_ls_wR_factor_ref     0.1554
_refine_ls_goodness_of_fit_ref     1.122
_refine_ls_restrained_S_all     1.122
_refine_ls_number_reflns     6133
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0532P)²+2.5558P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.367
_refine_diff_density_min     -0.424
_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
    'Ti' 'Ti' 0.2776 0.4457
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0140 0.0100
                         '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'
    '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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'STADI4 (Stoe & Cie, 1998)'
_computing_cell_refinement     'STADI4 (Stoe & Cie, 1998)'
_computing_data_reduction     'X-RED (Stoe & Cie, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg, 2001)'
_computing_publication_material     'enCIFer (Allen et al.,  2004)'
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
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Ti Ti1 0.18135(5) 0.59284(10) 0.60307(4) 0.02406(18) Uani d . 1 . .
    Ti Ti2 0.70766(5) 0.58675(11) 0.64839(4) 0.0319(2) Uani d . 1 . .
    F F1 0.1489(3) 0.5816(4) 0.51539(14) 0.0687(10) Uani d . 1 . .
    F F2 0.07464(18) 0.5254(4) 0.60403(17) 0.0582(9) Uani d . 1 . .
    F F3 0.29513(18) 0.6604(4) 0.61299(17) 0.0539(8) Uani d . 1 . .
    F F4 0.14665(19) 0.8126(3) 0.59720(15) 0.0469(7) Uani d . 1 . .
    F F5 0.2192(2) 0.3737(3) 0.61004(16) 0.0492(8) Uani d . 1 . .
    F F6 0.2182(2) 0.6079(5) 0.69502(13) 0.0557(9) Uani d . 1 . .
    F F7 0.72742(19) 0.7113(4) 0.58528(14) 0.0518(8) Uani d . 1 . .
    F F8 0.6614(2) 0.4174(4) 0.59328(14) 0.0631(10) Uani d . 1 . .
    F F9 0.5986(2) 0.6765(4) 0.6291(2) 0.0817(13) Uani d . 1 . .
    F F10 0.81774(18) 0.4997(4) 0.66930(15) 0.0494(8) Uani d . 1 . .
    F F11 0.7527(2) 0.7485(4) 0.70991(15) 0.0533(8) Uani d . 1 . .
    F F12 0.6933(2) 0.4627(4) 0.71561(15) 0.0555(9) Uani d . 1 . .
    N N1 0.4459(2) 0.1509(5) 0.60450(17) 0.0276(8) Uani d . 1 . .
    C C1 0.5134(3) 0.0224(6) 0.6192(2) 0.0361(11) Uani d . 1 . .
    H H1A 0.5186 -0.0159 0.5785 0.044(2) Uiso calc R 1 . .
    H H1B 0.4952 -0.0708 0.6394 0.044(2) Uiso calc R 1 . .
    C C2 0.6020(3) 0.0814(6) 0.6642(2) 0.0342(10) Uani d . 1 . .
    H H2A 0.6448 -0.0063 0.6703 0.044(2) Uiso calc R 1 . .
    H H2B 0.6206 0.1748 0.6444 0.044(2) Uiso calc R 1 . .
    N N2 0.5983(2) 0.1311(5) 0.72899(18) 0.0333(9) Uani d . 1 . .
    H H2C 0.5635 0.2188 0.7239 0.044(2) Uiso calc R 1 . .
    H H2D 0.6521 0.1565 0.7560 0.044(2) Uiso calc R 1 . .
    H H2E 0.5773 0.0479 0.7458 0.044(2) Uiso calc R 1 . .
    C C3 0.4511(3) 0.2578(6) 0.5509(2) 0.0392(12) Uani d . 1 . .
    H H3A 0.4246 0.2012 0.5093 0.044(2) Uiso calc R 1 . .
    H H3B 0.5123 0.2784 0.5571 0.044(2) Uiso calc R 1 . .
    C C4 0.4048(3) 0.4209(7) 0.5489(2) 0.0418(12) Uani d . 1 . .
    H H4A 0.4078 0.4863 0.5124 0.044(2) Uiso calc R 1 . .
    H H4B 0.3434 0.4006 0.5419 0.044(2) Uiso calc R 1 . .
    N N3 0.4453(3) 0.5149(5) 0.61097(19) 0.0379(9) Uani d . 1 . .
    H H3C 0.4595 0.4455 0.6448 0.044(2) Uiso calc R 1 . .
    H H3D 0.4073 0.5894 0.6150 0.044(2) Uiso calc R 1 . .
    H H3E 0.4935 0.5660 0.6103 0.044(2) Uiso calc R 1 . .
    C C5 0.3582(3) 0.0778(7) 0.5890(2) 0.0394(11) Uani d . 1 . .
    H H5A 0.3532 -0.0187 0.5615 0.044(2) Uiso calc R 1 . .
    H H5B 0.3142 0.1572 0.5645 0.044(2) Uiso calc R 1 . .
    C C6 0.3406(3) 0.0281(6) 0.6498(3) 0.0399(12) Uani d . 1 . .
    H H6A 0.2837 -0.0253 0.6373 0.044(2) Uiso calc R 1 . .
    H H6B 0.3847 -0.0512 0.6743 0.044(2) Uiso calc R 1 . .
    N N4 0.3420(2) 0.1714(5) 0.69203(18) 0.0375(10) Uani d . 1 . .
    H H4C 0.3941 0.2208 0.7036 0.044(2) Uiso calc R 1 . .
    H H4D 0.3325 0.1373 0.7278 0.044(2) Uiso calc R 1 . .
    H H4E 0.3002 0.2425 0.6702 0.044(2) Uiso calc R 1 . .
    N N5 0.0735(2) 0.5437(4) 0.89540(17) 0.0257(8) Uani d . 1 . .
    C C7 -0.0032(3) 0.6180(6) 0.9046(2) 0.0303(10) Uani d . 1 . .
    H H7A 0.0129 0.7239 0.9263 0.044(2) Uiso calc R 1 . .
    H H7B -0.0232 0.5471 0.9324 0.044(2) Uiso calc R 1 . .
    C C8 -0.0768(3) 0.6422(6) 0.8393(2) 0.0371(11) Uani d . 1 . .
    H H8A -0.1257 0.6977 0.8462 0.044(2) Uiso calc R 1 . .
    H H8B -0.0566 0.7112 0.8111 0.044(2) Uiso calc R 1 . .
    N N6 -0.1063(2) 0.4800(5) 0.80724(18) 0.0396(10) Uani d . 1 . .
    H H6C -0.0602 0.4245 0.8049 0.044(2) Uiso calc R 1 . .
    H H6D -0.1447 0.4962 0.7670 0.044(2) Uiso calc R 1 . .
    H H6E -0.1316 0.4222 0.8305 0.044(2) Uiso calc R 1 . .
    C C9 0.1286(3) 0.4546(6) 0.9547(2) 0.0330(10) Uani d . 1 . .
    H H9A 0.1348 0.5216 0.9930 0.044(2) Uiso calc R 1 . .
    H H9B 0.1867 0.4386 0.9526 0.044(2) Uiso calc R 1 . .
    C C10 0.0905(3) 0.2884(6) 0.9620(2) 0.0324(10) Uani d . 1 . .
    H H10A 0.1238 0.2425 1.0047 0.044(2) Uiso calc R 1 . .
    H H10B 0.0304 0.3030 0.9598 0.044(2) Uiso calc R 1 . .
    N N7 0.0924(3) 0.1710(5) 0.91024(19) 0.0350(9) Uani d . 1 . .
    H H7C 0.0633 0.2141 0.8710 0.044(2) Uiso calc R 1 . .
    H H7D 0.0673 0.0763 0.9148 0.044(2) Uiso calc R 1 . .
    H H7E 0.1478 0.1522 0.9138 0.044(2) Uiso calc R 1 . .
    C C11 0.1253(3) 0.6685(5) 0.8757(2) 0.0309(10) Uani d . 1 . .
    H H11A 0.1671 0.7186 0.9147 0.044(2) Uiso calc R 1 . .
    H H11B 0.0864 0.7548 0.8508 0.044(2) Uiso calc R 1 . .
    C C12 0.1743(3) 0.5946(6) 0.8347(2) 0.0319(10) Uani d . 1 . .
    H H12A 0.2105 0.6789 0.8252 0.044(2) Uiso calc R 1 . .
    H H12B 0.2126 0.5069 0.8592 0.044(2) Uiso calc R 1 . .
    N N8 0.1116(2) 0.5266(5) 0.77194(18) 0.0329(9) Uani d . 1 . .
    H H8C 0.0850 0.4378 0.7804 0.044(2) Uiso calc R 1 . .
    H H8D 0.1408 0.4986 0.7458 0.044(2) Uiso calc R 1 . .
    H H8E 0.0716 0.6030 0.7523 0.044(2) Uiso calc R 1 . .
    F F13 0.48067(17) 0.3777(3) 0.73054(12) 0.0381(6) Uani d . 1 . .
    F F14 0.00692(17) 0.2652(3) 0.78508(13) 0.0362(6) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Ti1 F1 . 1.796(3) y
    Ti1 F2 . 1.826(3) y
    Ti1 F4 . 1.856(3) y
    Ti1 F5 . 1.865(3) y
    Ti1 F3 . 1.868(3) y
    Ti1 F6 . 1.882(3) y
    Ti2 F8 . 1.803(3) y
    Ti2 F7 . 1.821(3) y
    Ti2 F9 . 1.825(3) y
    Ti2 F10 . 1.827(3) y
    Ti2 F11 . 1.832(3) y
    Ti2 F12 . 1.856(3) y
    N1 C1 . 1.463(6) ?
    N1 C5 . 1.470(6) ?
    N1 C3 . 1.479(6) ?
    C1 C2 . 1.507(6) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 N2 . 1.487(6) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    N2 H2C . 0.8900 ?
    N2 H2D . 0.8900 ?
    N2 H2E . 0.8900 ?
    C3 C4 . 1.512(7) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 N3 . 1.489(6) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    N3 H3C . 0.8900 ?
    N3 H3D . 0.8900 ?
    N3 H3E . 0.8900 ?
    C5 C6 . 1.504(7) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 N4 . 1.475(6) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    N4 H4C . 0.8900 ?
    N4 H4D . 0.8900 ?
    N4 H4E . 0.8900 ?
    N5 C7 . 1.459(5) ?
    N5 C11 . 1.472(5) ?
    N5 C9 . 1.475(5) ?
    C7 C8 . 1.516(6) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 N6 . 1.484(6) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    N6 H6C . 0.8900 ?
    N6 H6D . 0.8900 ?
    N6 H6E . 0.8900 ?
    C9 C10 . 1.512(6) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 N7 . 1.483(6) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    N7 H7C . 0.8900 ?
    N7 H7D . 0.8900 ?
    N7 H7E . 0.8900 ?
    C11 C12 . 1.513(6) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 N8 . 1.494(6) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    N8 H8C . 0.8900 ?
    N8 H8D . 0.8900 ?
    N8 H8E . 0.8900 ?
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
    F1 Ti1 F2 . . 94.09(17) n
    F1 Ti1 F4 . . 90.38(15) n
    F2 Ti1 F4 . . 91.12(14) n
    F1 Ti1 F5 . . 90.21(15) n
    F2 Ti1 F5 . . 90.17(14) n
    F4 Ti1 F5 . . 178.55(14) n
    F1 Ti1 F3 . . 92.71(17) n
    F2 Ti1 F3 . . 173.16(16) n
    F4 Ti1 F3 . . 89.59(14) n
    F5 Ti1 F3 . . 89.06(14) n
    F1 Ti1 F6 . . 178.38(17) n
    F2 Ti1 F6 . . 87.50(15) n
    F4 Ti1 F6 . . 89.26(15) n
    F5 Ti1 F6 . . 90.11(15) n
    F3 Ti1 F6 . . 85.71(15) n
    F8 Ti2 F7 . . 93.49(14) n
    F8 Ti2 F9 . . 90.23(18) n
    F7 Ti2 F9 . . 91.21(16) n
    F8 Ti2 F10 . . 90.95(16) n
    F7 Ti2 F10 . . 89.10(15) n
    F9 Ti2 F10 . . 178.75(19) n
    F8 Ti2 F11 . . 175.05(15) n
    F7 Ti2 F11 . . 91.46(15) n
    F9 Ti2 F11 . . 89.50(18) n
    F10 Ti2 F11 . . 89.29(15) n
    F8 Ti2 F12 . . 88.59(14) n
    F7 Ti2 F12 . . 177.05(15) n
    F9 Ti2 F12 . . 90.86(17) n
    F10 Ti2 F12 . . 88.78(15) n
    F11 Ti2 F12 . . 86.47(14) n
    C1 N1 C5 . . 111.0(4) ?
    C1 N1 C3 . . 110.0(4) ?
    C5 N1 C3 . . 111.9(4) ?
    N1 C1 C2 . . 112.9(4) ?
    N1 C1 H1A . . 109.0 ?
    C2 C1 H1A . . 109.0 ?
    N1 C1 H1B . . 109.0 ?
    C2 C1 H1B . . 109.0 ?
    H1A C1 H1B . . 107.8 ?
    N2 C2 C1 . . 110.8(4) ?
    N2 C2 H2A . . 109.5 ?
    C1 C2 H2A . . 109.5 ?
    N2 C2 H2B . . 109.5 ?
    C1 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 108.1 ?
    C2 N2 H2C . . 109.5 ?
    C2 N2 H2D . . 109.5 ?
    H2C N2 H2D . . 109.5 ?
    C2 N2 H2E . . 109.5 ?
    H2C N2 H2E . . 109.5 ?
    H2D N2 H2E . . 109.5 ?
    N1 C3 C4 . . 111.6(4) ?
    N1 C3 H3A . . 109.3 ?
    C4 C3 H3A . . 109.3 ?
    N1 C3 H3B . . 109.3 ?
    C4 C3 H3B . . 109.3 ?
    H3A C3 H3B . . 108.0 ?
    N3 C4 C3 . . 111.2(4) ?
    N3 C4 H4A . . 109.4 ?
    C3 C4 H4A . . 109.4 ?
    N3 C4 H4B . . 109.4 ?
    C3 C4 H4B . . 109.4 ?
    H4A C4 H4B . . 108.0 ?
    C4 N3 H3C . . 109.5 ?
    C4 N3 H3D . . 109.5 ?
    H3C N3 H3D . . 109.5 ?
    C4 N3 H3E . . 109.5 ?
    H3C N3 H3E . . 109.5 ?
    H3D N3 H3E . . 109.5 ?
    N1 C5 C6 . . 112.0(4) ?
    N1 C5 H5A . . 109.2 ?
    C6 C5 H5A . . 109.2 ?
    N1 C5 H5B . . 109.2 ?
    C6 C5 H5B . . 109.2 ?
    H5A C5 H5B . . 107.9 ?
    N4 C6 C5 . . 111.9(4) ?
    N4 C6 H6A . . 109.2 ?
    C5 C6 H6A . . 109.2 ?
    N4 C6 H6B . . 109.2 ?
    C5 C6 H6B . . 109.2 ?
    H6A C6 H6B . . 107.9 ?
    C6 N4 H4C . . 109.5 ?
    C6 N4 H4D . . 109.5 ?
    H4C N4 H4D . . 109.5 ?
    C6 N4 H4E . . 109.5 ?
    H4C N4 H4E . . 109.5 ?
    H4D N4 H4E . . 109.5 ?
    C7 N5 C11 . . 111.2(3) ?
    C7 N5 C9 . . 111.6(3) ?
    C11 N5 C9 . . 110.8(3) ?
    N5 C7 C8 . . 110.9(4) ?
    N5 C7 H7A . . 109.5 ?
    C8 C7 H7A . . 109.5 ?
    N5 C7 H7B . . 109.5 ?
    C8 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 108.0 ?
    N6 C8 C7 . . 110.2(4) ?
    N6 C8 H8A . . 109.6 ?
    C7 C8 H8A . . 109.6 ?
    N6 C8 H8B . . 109.6 ?
    C7 C8 H8B . . 109.6 ?
    H8A C8 H8B . . 108.1 ?
    C8 N6 H6C . . 109.5 ?
    C8 N6 H6D . . 109.5 ?
    H6C N6 H6D . . 109.5 ?
    C8 N6 H6E . . 109.5 ?
    H6C N6 H6E . . 109.5 ?
    H6D N6 H6E . . 109.5 ?
    N5 C9 C10 . . 112.4(3) ?
    N5 C9 H9A . . 109.1 ?
    C10 C9 H9A . . 109.1 ?
    N5 C9 H9B . . 109.1 ?
    C10 C9 H9B . . 109.1 ?
    H9A C9 H9B . . 107.9 ?
    N7 C10 C9 . . 111.7(4) ?
    N7 C10 H10A . . 109.3 ?
    C9 C10 H10A . . 109.3 ?
    N7 C10 H10B . . 109.3 ?
    C9 C10 H10B . . 109.3 ?
    H10A C10 H10B . . 107.9 ?
    C10 N7 H7C . . 109.5 ?
    C10 N7 H7D . . 109.5 ?
    H7C N7 H7D . . 109.5 ?
    C10 N7 H7E . . 109.5 ?
    H7C N7 H7E . . 109.5 ?
    H7D N7 H7E . . 109.5 ?
    N5 C11 C12 . . 112.0(4) ?
    N5 C11 H11A . . 109.2 ?
    C12 C11 H11A . . 109.2 ?
    N5 C11 H11B . . 109.2 ?
    C12 C11 H11B . . 109.2 ?
    H11A C11 H11B . . 107.9 ?
    N8 C12 C11 . . 110.7(3) ?
    N8 C12 H12A . . 109.5 ?
    C11 C12 H12A . . 109.5 ?
    N8 C12 H12B . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    C12 N8 H8C . . 109.5 ?
    C12 N8 H8D . . 109.5 ?
    H8C N8 H8D . . 109.5 ?
    C12 N8 H8E . . 109.5 ?
    H8C N8 H8E . . 109.5 ?
    H8D N8 H8E . . 109.5 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N2 H2C F13 . 0.89 1.90 2.773(5) 165
    N2 H2D F6 2_646 0.89 2.04 2.865(5) 154
    N2 H2E F13 2_646 0.89 1.84 2.725(5) 172
    N3 H3C F13 . 0.89 1.86 2.700(5) 157
    N3 H3C N1 . 0.89 2.52 2.948(6) 110
    N3 H3D F3 . 0.89 1.90 2.726(5) 154
    N3 H3E F9 . 0.89 1.84 2.717(5) 167
    N4 H4C F13 . 0.89 1.83 2.692(5) 162
    N4 H4D F12 2_646 0.89 2.01 2.835(5) 153
    N4 H4E F5 . 0.89 1.84 2.712(5) 168
    N6 H6C F14 . 0.89 1.84 2.696(5) 162
    N6 H6D F10 1_455 0.89 2.00 2.823(5) 154
    N6 H6E F4 2_546 0.89 1.90 2.749(5) 160
    N7 H7C F14 . 0.89 1.82 2.699(5) 169
    N7 H7D F2 2_546 0.89 2.24 2.876(5) 129
    N7 H7E F7 2_646 0.89 2.08 2.916(5) 157
    N7 H7E F10 2_646 0.89 2.41 2.972(5) 121
    N8 H8C F14 . 0.89 1.91 2.791(5) 168
    N8 H8D F6 . 0.89 2.14 2.879(5) 140
    N8 H8E F14 2_556 0.89 1.81 2.702(5) 177
