##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2006-12-09
_journal_date_accepted     2006-12-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      3
_journal_page_first     o1138
_journal_page_last     o1139
_journal_paper_category     EO
_journal_coeditor_code     CV2167
_publ_contact_author_name     'Luis Alvarez-Thon'
_publ_contact_author_address
;Departamento de Ciencias Químicas
Universidad Andrés Bello
República 275
Santiago de Chile
Chile
;
_publ_contact_author_email     quaternionic@gmail.com
_publ_section_title
;\
3,5-Dimethyl-1-(4-nitrophenyl)-4-[(E)-(2,3,4,5,6-pentafluorophenyl)\
diazenyl]- 1H-pyrazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Bustos, Carlos'
;Instituto de Química
Universidad Austral de Chile
Avda. Los Robles s/n
Campus Isla Teja
Casilla 567
Valdivia
Chile
;
    'Sánchez, Cristian'
;Instituto de Química
Universidad Austral de Chile
Avda. Los Robles s/n
Campus Isla Teja
Casilla 567
Valdivia
Chile
;
    'Schott, Eduardo'
;Instituto de Química
Universidad Austral de Chile
Avda. Los Robles s/n
Campus Isla Teja
Casilla 567
Valdivia
Chile
;
    'Alvarez-Thon, Luis'
;Departamento de Ciencias Químicas
Universidad Andrés Bello
República 275
Santiago de Chile
Chile
;
    'Fuentealba, Mauricio'
;CIMAT, Laboratorio de Cristalografía
Facultad de Ciencias Físicas y Matemáticas
Universidad de Chile
Casilla 487-3
Santiago de Chile
Chile
;
data_I
_chemical_name_systematic
;
3,5-Dimethyl-1-(4-nitrophenyl)-4-[(E)-(2,3,4,5,6-pentafluorophenyl)diazenyl]-
1H-pyrazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H10 F5 N5 O2'
_chemical_formula_sum     'C17 H10 F5 N5 O2'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C17 H10 F5 N5 O2'
_chemical_formula_weight     411.30
_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_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,1/2+y,1/2-z
    3 -x,-y,-z
    4 x,1/2-y,1/2+z
_cell_length_a     5.9868(16)
_cell_length_b     15.073(4)
_cell_length_c     19.010(5)
_cell_angle_alpha     90
_cell_angle_beta     92.557(4)
_cell_angle_gamma     90
_cell_volume     1713.7(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     999
_cell_measurement_theta_min     1.72
_cell_measurement_theta_max     27.88
_cell_measurement_temperature     298
_cell_special_details
;
;
_exptl_crystal_description     'block'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.18
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.594
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     832
_exptl_absorpt_coefficient_mu     0.145
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details
;
;
_exptl_special_details
;
;
_diffrn_ambient_temperature     298
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     ?
_diffrn_radiation_monochromator     ?
_diffrn_measurement_device_type     'Bruker CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11887
_diffrn_reflns_av_R_equivalents     0.0690
_diffrn_reflns_av_sigmaI/netI     0.0707
_diffrn_reflns_theta_min     1.72
_diffrn_reflns_theta_max     27.88
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.926
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_reflns_reduction_process
;
;
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     3777
_reflns_number_gt     1999
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1267
_refine_ls_R_factor_gt     0.0612
_refine_ls_wR_factor_gt     0.1289
_refine_ls_wR_factor_ref     0.1496
_refine_ls_goodness_of_fit_ref     0.98
_refine_ls_restrained_S_all     0.98
_refine_ls_number_reflns     3777
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     'constr'
_refine_ls_weighting_scheme     'calc'
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0618P)²] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.20
_refine_diff_density_min     -0.21
_refine_ls_extinction_method     'none'
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    F F 0.0171 0.0103 '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'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT  (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP in SHELXTL-PC (Sheldrick, 1994)'
_computing_publication_material
                  'PLATON (Spek, 2003) and MERCURY (Bruno et al.,  2002)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    F F1 0.1643(3) 0.71657(11) 0.10809(9) 0.0597(6) Uani . . 1.000
    F F2 0.0745(3) 0.70454(14) -0.03046(9) 0.0767(8) Uani . . 1.000
    F F3 0.3745(4) 0.62747(14) -0.11379(9) 0.0893(9) Uani . . 1.000
    F F4 0.7570(3) 0.55895(13) -0.05658(10) 0.0789(8) Uani . . 1.000
    F F5 0.8415(3) 0.56571(12) 0.08264(10) 0.0664(7) Uani . . 1.000
    O O1 0.1088(5) 0.5404(2) 0.67421(14) 0.1125(14) Uani . . 1.000
    O O2 0.4056(5) 0.5961(2) 0.72094(13) 0.1023(13) Uani . . 1.000
    N N1 0.5530(4) 0.64919(15) 0.17185(11) 0.0446(8) Uani . . 1.000
    N N2 0.7340(4) 0.70165(16) 0.19368(11) 0.0473(8) Uani . . 1.000
    N N3 0.4808(4) 0.62588(16) 0.35154(12) 0.0501(9) Uani . . 1.000
    N N4 0.5964(4) 0.65594(16) 0.40305(12) 0.0490(9) Uani . . 1.000
    N N5 0.2895(6) 0.5750(2) 0.67027(15) 0.0712(11) Uani . . 1.000
    C C1 0.5035(5) 0.64124(18) 0.09889(13) 0.0400(9) Uani . . 1.000
    C C2 0.3100(5) 0.67557(19) 0.06816(15) 0.0443(10) Uani . . 1.000
    C C3 0.2647(5) 0.6702(2) -0.00241(15) 0.0512(11) Uani . . 1.000
    C C4 0.4163(6) 0.6322(2) -0.04485(15) 0.0545(11) Uani . . 1.000
    C C5 0.6094(5) 0.5982(2) -0.01600(15) 0.0517(11) Uani . . 1.000
    C C6 0.6531(5) 0.60217(19) 0.05563(15) 0.0462(10) Uani . . 1.000
    C C7 0.4408(5) 0.61697(19) 0.22597(14) 0.0430(10) Uani . . 1.000
    C C8 0.5538(5) 0.64837(19) 0.28557(14) 0.0439(10) Uani . . 1.000
    C C9 0.7336(5) 0.7005(2) 0.26259(14) 0.0469(10) Uani . . 1.000
    C C10 0.5110(5) 0.63118(18) 0.46892(14) 0.0427(10) Uani . . 1.000
    C C11 0.3031(5) 0.59359(19) 0.47665(15) 0.0494(11) Uani . . 1.000
    C C12 0.2325(5) 0.5735(2) 0.54273(16) 0.0527(11) Uani . . 1.000
    C C13 0.3709(5) 0.59210(19) 0.60019(14) 0.0473(10) Uani . . 1.000
    C C14 0.5780(5) 0.62854(19) 0.59387(14) 0.0505(11) Uani . . 1.000
    C C15 0.6473(5) 0.64830(19) 0.52767(14) 0.0476(10) Uani . . 1.000
    C C16 0.2455(5) 0.5580(2) 0.21778(15) 0.0608(11) Uani . . 1.000
    C C17 0.9066(6) 0.7508(2) 0.30423(16) 0.0735(14) Uani . . 1.000
    H H11 0.21070 0.58180 0.43710 0.0590 Uiso calc R 1.000
    H H12 0.09330 0.54770 0.54830 0.0630 Uiso calc R 1.000
    H H14 0.67030 0.63970 0.63350 0.0610 Uiso calc R 1.000
    H H15 0.78740 0.67350 0.52250 0.0570 Uiso calc R 1.000
    H H16A 0.11840 0.59150 0.20030 0.0910 Uiso calc R 1.000
    H H16B 0.21410 0.53260 0.26260 0.0910 Uiso calc R 1.000
    H H16C 0.27660 0.51150 0.18510 0.0910 Uiso calc R 1.000
    H H17A 0.99480 0.71050 0.33300 0.1100 Uiso calc R 1.000
    H H17B 0.83550 0.79300 0.33380 0.1100 Uiso calc R 1.000
    H H17C 1.00140 0.78150 0.27290 0.1100 Uiso calc R 1.000
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    F1 C2 . . 1.333(3) n
    F2 C3 . . 1.340(4) no
    F3 C4 . . 1.325(3) no
    F4 C5 . . 1.337(4) no
    F5 C6 . . 1.337(3) no
    O1 N5 . . 1.206(5) n
    O2 N5 . . 1.205(4) n
    N1 N2 . . 1.390(3) n
    N1 C1 . . 1.410(3) n
    N1 C7 . . 1.344(4) n
    N2 C9 . . 1.310(3) n
    N3 N4 . . 1.258(3) n
    N3 C8 . . 1.388(4) n
    N4 C10 . . 1.423(4) n
    N5 C13 . . 1.462(4) n
    C1 C2 . . 1.375(4) no
    C1 C6 . . 1.375(4) no
    C2 C3 . . 1.359(4) no
    C3 C4 . . 1.367(4) no
    C4 C5 . . 1.358(5) no
    C5 C6 . . 1.376(4) no
    C7 C8 . . 1.377(4) n
    C7 C16 . . 1.471(4) no
    C8 C9 . . 1.417(4) n
    C9 C17 . . 1.484(4) no
    C10 C11 . . 1.381(4) no
    C10 C15 . . 1.378(4) no
    C11 C12 . . 1.377(4) no
    C12 C13 . . 1.370(4) no
    C13 C14 . . 1.366(4) no
    C14 C15 . . 1.375(4) no
    C11 H11 . . 0.9300 no
    C12 H12 . . 0.9300 no
    C14 H14 . . 0.9300 no
    C15 H15 . . 0.9300 no
    C16 H16A . . 0.9600 no
    C16 H16B . . 0.9600 no
    C16 H16C . . 0.9600 no
    C17 H17A . . 0.9600 no
    C17 H17B . . 0.9600 no
    C17 H17C . . 0.9600 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    F1 F2 2.671(3) . . no
    F1 F5 3.009(3) . 1_455 no
    F1 N1 2.768(3) . . no
    F1 N2 3.116(3) . 1_455 no
    F1 C7 3.112(3) . . no
    F1 C16 3.195(3) . . no
    F1 C13 3.144(3) . 4_564 no
    F2 C17 3.325(4) . 4_464 no
    F2 F1 2.671(3) . . no
    F2 F3 2.709(3) . . no
    F2 F4 2.931(3) . 1_455 no
    F2 C5 3.235(4) . 1_455 no
    F2 C11 3.337(4) . 4_564 no
    F3 F4 2.697(3) . . no
    F3 F2 2.709(3) . . no
    F4 F2 2.931(3) . 1_655 no
    F4 F5 3.108(3) . 3_765 no
    F4 F3 2.697(3) . . no
    F4 F5 2.674(3) . . no
    F5 F4 3.108(3) . 3_765 no
    F5 F4 2.674(3) . . no
    F5 N1 2.776(3) . . no
    F5 F1 3.009(3) . 1_655 no
    F5 C2 3.279(4) . 1_655 no
    F5 N2 3.032(3) . . no
    F1 H16A 2.6000 . . no
    F2 H15 2.7400 . 4_464 no
    F4 H16C 2.6600 . 3_665 no
    F5 H16A 2.7500 . 1_655 no
    O1 C16 3.362(4) . 3_566 no
    O2 C16 3.301(4) . 3_666 no
    O1 H12 2.3900 . . no
    O1 H16B 2.5700 . 3_566 no
    O2 H14 2.4400 . . no
    N1 F1 2.768(3) . . no
    N1 F5 2.776(3) . . no
    N2 F1 3.116(3) . 1_655 no
    N2 F5 3.032(3) . . no
    N2 C14 3.296(4) . 4_564 no
    N4 C17 3.055(4) . . no
    N2 H16A 2.8400 . 1_655 no
    N2 H14 2.6700 . 4_564 no
    N3 H11 2.4400 . . no
    N3 H16B 2.6700 . . no
    N4 H17A 2.9000 . . no
    N4 H17B 2.8700 . . no
    C1 C14 3.501(4) . 4_564 no
    C1 C15 3.570(4) . 4_564 no
    C2 C14 3.386(4) . 4_564 no
    C2 F5 3.279(4) . 1_455 no
    C2 C16 3.388(4) . . no
    C2 C15 3.443(4) . 4_564 no
    C2 C13 3.570(4) . 4_564 no
    C3 C11 3.591(4) . 4_564 no
    C3 C15 3.597(4) . 4_564 no
    C3 C10 3.392(4) . 4_564 no
    C4 C6 3.562(4) . 3_665 no
    C5 C6 3.472(4) . 3_665 no
    C5 F2 3.235(4) . 1_655 no
    C5 C5 3.305(4) . 3_665 no
    C6 C4 3.562(4) . 3_665 no
    C6 C5 3.472(4) . 3_665 no
    C7 F1 3.112(3) . . no
    C10 C3 3.392(4) . 4_565 no
    C10 C12 3.458(4) . 3_666 no
    C11 C3 3.591(4) . 4_565 no
    C11 F2 3.337(4) . 4_565 no
    C12 C10 3.458(4) . 3_666 no
    C13 C2 3.570(4) . 4_565 no
    C13 F1 3.144(3) . 4_565 no
    C14 N2 3.296(4) . 4_565 no
    C14 C2 3.386(4) . 4_565 no
    C14 C1 3.501(4) . 4_565 no
    C15 C1 3.570(4) . 4_565 no
    C15 C3 3.597(4) . 4_565 no
    C15 C2 3.443(4) . 4_565 no
    C16 O1 3.362(4) . 3_566 no
    C16 F1 3.195(3) . . no
    C16 O2 3.301(4) . 3_666 no
    C16 C2 3.388(4) . . no
    C17 N4 3.055(4) . . no
    C17 F2 3.325(4) . 4_665 no
    C1 H16C 2.9200 . . no
    C2 H16A 3.0800 . . no
    C12 H15 3.0700 . 1_455 no
    C15 H12 3.0800 . 1_655 no
    H11 N3 2.4400 . . no
    H12 O1 2.3900 . . no
    H12 C15 3.0800 . 1_455 no
    H12 H12 2.5500 . 3_566 no
    H14 O2 2.4400 . . no
    H14 N2 2.6700 . 4_565 no
    H15 C12 3.0700 . 1_655 no
    H15 F2 2.7400 . 4_665 no
    H16A F1 2.6000 . . no
    H16A F5 2.7500 . 1_455 no
    H16A N2 2.8400 . 1_455 no
    H16A C2 3.0800 . . no
    H16B N3 2.6700 . . no
    H16B O1 2.5700 . 3_566 no
    H16C C1 2.9200 . . no
    H16C F4 2.6600 . 3_665 no
    H17A N4 2.9000 . . no
    H17B N4 2.8700 . . no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 N1 C1 . . . 118.0(2) n
    N2 N1 C7 . . . 112.7(2) no
    C1 N1 C7 . . . 129.2(2) no
    N1 N2 C9 . . . 104.8(2) no
    N4 N3 C8 . . . 115.5(2) n
    N3 N4 C10 . . . 112.6(2) n
    O1 N5 O2 . . . 123.5(3) no
    O1 N5 C13 . . . 118.0(3) no
    O2 N5 C13 . . . 118.6(3) no
    N1 C1 C2 . . . 121.5(3) no
    N1 C1 C6 . . . 120.7(3) no
    C2 C1 C6 . . . 117.8(2) no
    F1 C2 C1 . . . 119.5(2) no
    F1 C2 C3 . . . 118.9(3) no
    C1 C2 C3 . . . 121.6(3) no
    F2 C3 C2 . . . 119.9(3) no
    F2 C3 C4 . . . 120.1(3) no
    C2 C3 C4 . . . 119.9(3) no
    F3 C4 C3 . . . 120.4(3) no
    F3 C4 C5 . . . 119.9(3) no
    C3 C4 C5 . . . 119.7(3) no
    F4 C5 C4 . . . 120.5(3) no
    F4 C5 C6 . . . 119.3(3) no
    C4 C5 C6 . . . 120.3(3) no
    F5 C6 C1 . . . 120.5(3) no
    F5 C6 C5 . . . 118.8(3) no
    C1 C6 C5 . . . 120.7(3) no
    N1 C7 C8 . . . 105.2(2) no
    N1 C7 C16 . . . 124.0(2) no
    C8 C7 C16 . . . 130.8(3) no
    N3 C8 C7 . . . 119.8(3) no
    N3 C8 C9 . . . 133.5(3) no
    C7 C8 C9 . . . 106.8(2) no
    N2 C9 C8 . . . 110.5(3) no
    N2 C9 C17 . . . 119.6(3) no
    C8 C9 C17 . . . 129.8(3) no
    N4 C10 C11 . . . 124.2(3) no
    N4 C10 C15 . . . 116.2(3) no
    C11 C10 C15 . . . 119.6(3) no
    C10 C11 C12 . . . 120.1(3) no
    C11 C12 C13 . . . 118.9(3) no
    N5 C13 C12 . . . 118.4(3) no
    N5 C13 C14 . . . 119.5(3) no
    C12 C13 C14 . . . 122.1(3) no
    C13 C14 C15 . . . 118.7(3) no
    C10 C15 C14 . . . 120.6(3) no
    C10 C11 H11 . . . 120.00 no
    C12 C11 H11 . . . 120.00 no
    C11 C12 H12 . . . 121.00 no
    C13 C12 H12 . . . 121.00 no
    C13 C14 H14 . . . 121.00 no
    C15 C14 H14 . . . 121.00 no
    C10 C15 H15 . . . 120.00 no
    C14 C15 H15 . . . 120.00 no
    C7 C16 H16A . . . 109.00 no
    C7 C16 H16B . . . 109.00 no
    C7 C16 H16C . . . 109.00 no
    H16A C16 H16B . . . 109.00 no
    H16A C16 H16C . . . 109.00 no
    H16B C16 H16C . . . 110.00 no
    C9 C17 H17A . . . 110.00 no
    C9 C17 H17B . . . 109.00 no
    C9 C17 H17C . . . 109.00 no
    H17A C17 H17B . . . 109.00 no
    H17A C17 H17C . . . 109.00 no
    H17B C17 H17C . . . 109.00 no
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 N1 N2 C9 . . . . 177.0(2) no
    C7 N1 N2 C9 . . . . 0.7(3) no
    N2 N1 C1 C2 . . . . -113.4(3) n
    N2 N1 C1 C6 . . . . 63.7(3) n
    C7 N1 C1 C2 . . . . 62.2(4) no
    C7 N1 C1 C6 . . . . -120.8(3) no
    N2 N1 C7 C8 . . . . -0.8(3) no
    N2 N1 C7 C16 . . . . -178.6(3) no
    C1 N1 C7 C8 . . . . -176.5(3) no
    C1 N1 C7 C16 . . . . 5.7(5) no
    N1 N2 C9 C8 . . . . -0.3(3) no
    N1 N2 C9 C17 . . . . -179.8(3) no
    C8 N3 N4 C10 . . . . 179.4(2) n
    N4 N3 C8 C7 . . . . 178.6(3) n
    N4 N3 C8 C9 . . . . -1.2(5) n
    N3 N4 C10 C11 . . . . -11.9(4) n
    N3 N4 C10 C15 . . . . 169.3(3) no
    O1 N5 C13 C12 . . . . 4.2(5) no
    O1 N5 C13 C14 . . . . -177.9(3) no
    O2 N5 C13 C12 . . . . -175.7(3) no
    O2 N5 C13 C14 . . . . 2.2(5) no
    N1 C1 C2 F1 . . . . -0.7(4) no
    N1 C1 C2 C3 . . . . 178.1(3) no
    C6 C1 C2 F1 . . . . -177.8(3) no
    C6 C1 C2 C3 . . . . 1.0(4) no
    N1 C1 C6 F5 . . . . 4.5(4) no
    N1 C1 C6 C5 . . . . -176.9(3) no
    C2 C1 C6 F5 . . . . -178.4(3) no
    C2 C1 C6 C5 . . . . 0.2(4) no
    F1 C2 C3 F2 . . . . -1.1(4) no
    F1 C2 C3 C4 . . . . 176.9(3) no
    C1 C2 C3 F2 . . . . -179.9(3) no
    C1 C2 C3 C4 . . . . -1.9(5) no
    F2 C3 C4 F3 . . . . -1.3(5) no
    F2 C3 C4 C5 . . . . 179.5(3) no
    C2 C3 C4 F3 . . . . -179.3(3) no
    C2 C3 C4 C5 . . . . 1.5(5) no
    F3 C4 C5 F4 . . . . -0.8(5) no
    F3 C4 C5 C6 . . . . -179.4(3) no
    C3 C4 C5 F4 . . . . 178.4(3) no
    C3 C4 C5 C6 . . . . -0.2(5) no
    F4 C5 C6 F5 . . . . -0.7(4) no
    F4 C5 C6 C1 . . . . -179.3(3) no
    C4 C5 C6 F5 . . . . 178.0(3) no
    C4 C5 C6 C1 . . . . -0.6(5) no
    N1 C7 C8 N3 . . . . -179.3(2) no
    N1 C7 C8 C9 . . . . 0.6(3) no
    C16 C7 C8 N3 . . . . -1.7(5) no
    C16 C7 C8 C9 . . . . 178.1(3) no
    N3 C8 C9 N2 . . . . 179.7(3) no
    N3 C8 C9 C17 . . . . -1.0(6) no
    C7 C8 C9 N2 . . . . -0.1(3) no
    C7 C8 C9 C17 . . . . 179.2(3) no
    N4 C10 C11 C12 . . . . -178.6(3) no
    C15 C10 C11 C12 . . . . 0.1(4) no
    N4 C10 C15 C14 . . . . 178.6(3) no
    C11 C10 C15 C14 . . . . -0.2(4) no
    C10 C11 C12 C13 . . . . 0.5(4) no
    C11 C12 C13 N5 . . . . 176.7(3) no
    C11 C12 C13 C14 . . . . -1.1(5) no
    N5 C13 C14 C15 . . . . -176.8(3) no
    C12 C13 C14 C15 . . . . 1.0(4) no
    C13 C14 C15 C10 . . . . -0.4(4) no
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
    _geom_hbond_publ_flag
    C16 H16B O1 3_566 0.96 2.57 3.362(4) 140 yes
    C16 H16C F4 3_665 0.96 2.66 3.535(4) 151 no
    C15 H15 F2 4_665 0.93 2.74 3.597(4) 154 no
