##############################################################################
###                                                                        ###
###        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                                                              #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2007-11-03
_journal_date_accepted     2007-11-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     12
_journal_page_first     o4813
_journal_page_last     o4814
_journal_paper_category     QO
_journal_coeditor_code     IM2045
_publ_contact_author_name
;
A. Thiruvalluvar
;
_publ_contact_author_address
;
PG Research Department of Physics
Rajah Serfoji Government College (Autonomous)
Thanjavur-613 005
Tamil Nadu
India
;
_publ_contact_author_email     athiru@vsnl.net
_publ_contact_author_fax     'none'
_publ_contact_author_phone     '+91(4362)255490'
_publ_section_title
;\
1-{5-Methyl-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-1,2,3-triazol-4-yl}\
ethanone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'A. Thiruvalluvar'
;
?
;
;
PG Research Department of Physics
Rajah Serfoji Government College (Autonomous)
Thanjavur 613 005
Tamil Nadu
India
;
    'M. Subramanyam'
;
?
;
;
PG Research Department of Physics
Rajah Serfoji Government College (Autonomous)
Thanjavur 613 005
Tamil Nadu
India
;
    'R. J. Butcher'
;
?
;
;
Department of Chemistry,
Howard University,
525 College Street NW,
Washington, DC 20059,
USA
;
    'M. Mahalinga'
;
?
;
;
SeQuent Scientific Limited,
120 A&B Industrial area,
Baikampady,
New Mangalore 575 011,
India
;
data_I
_chemical_name_systematic
;
1-{5-Methyl-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-1,2,3-triazol-
4-yl}ethanone
;
_chemical_name_common     '1,2,3-triazole'
_chemical_formula_moiety     'C15 H11 F3 N4 O'
_chemical_formula_sum     'C15 H11 F3 N4 O'
_chemical_formula_structural     'C15 H11 F3 N4 O'
_chemical_formula_iupac     'C15 H11 F3 N4 O'
_chemical_formula_weight     320.28
_chemical_melting_point     459.0(10)
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,1/2+y,1/2-z
    3 -x,-y,-z
    4 1/2+x,1/2-y,1/2+z
_cell_length_a     11.7974(4)
_cell_length_b     8.2946(2)
_cell_length_c     14.6706(4)
_cell_angle_alpha     90
_cell_angle_beta     106.273(3)
_cell_angle_gamma     90
_cell_volume     1378.07(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5005
_cell_measurement_theta_min     4.6321
_cell_measurement_theta_max     32.5350
_cell_measurement_temperature     200(2)
_cell_special_details
;
?
;
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.44
_exptl_crystal_size_mid     0.37
_exptl_crystal_size_min     0.22
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.544
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.129
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_absorpt_correction_T_min     0.96234
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     200(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     10.5081
_diffrn_reflns_number     13863
_diffrn_reflns_av_R_equivalents     0.0265
_diffrn_reflns_av_sigmaI/netI     0.0499
_diffrn_reflns_theta_min     4.64
_diffrn_reflns_theta_max     32.60
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.917
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_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 > 2sigma(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     4615
_reflns_number_gt     2511
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0789
_refine_ls_R_factor_gt     0.0427
_refine_ls_wR_factor_gt     0.1161
_refine_ls_wR_factor_ref     0.1261
_refine_ls_goodness_of_fit_ref     0.963
_refine_ls_restrained_S_all     0.963
_refine_ls_number_reflns     4615
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0712P)²+0.0000P] 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     0.296
_refine_diff_density_min     -0.243
_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
    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     'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement     'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction     'CrysAlis RED  (Oxford Diffraction, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'PLATON (Spek, 2003)'
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 0.65453(7) 0.13558(11) 0.67581(5) 0.0531(3) Uani . . 1.000
    F F2 0.73949(7) -0.09155(11) 0.67264(5) 0.0470(3) Uani . . 1.000
    F F3 0.83628(7) 0.12893(9) 0.67695(5) 0.0445(3) Uani . . 1.000
    O O41 0.87328(10) 0.13080(14) -0.00685(7) 0.0567(4) Uani . . 1.000
    N N1 0.77553(9) -0.04634(13) 0.22873(7) 0.0309(3) Uani . . 1.000
    N N2 0.67283(10) -0.11480(14) 0.17371(7) 0.0410(4) Uani . . 1.000
    N N3 0.66767(9) -0.08334(14) 0.08593(7) 0.0380(3) Uani . . 1.000
    N N11 0.86194(9) -0.09327(13) 0.52759(7) 0.0303(3) Uani . . 1.000
    C C4 0.76499(10) 0.00397(14) 0.08307(8) 0.0296(3) Uani . . 1.000
    C C5 0.83557(10) 0.02833(14) 0.17441(8) 0.0281(3) Uani . . 1.000
    C C6 0.95054(10) 0.11275(16) 0.21160(9) 0.0343(4) Uani . . 1.000
    C C12 0.92664(11) -0.15856(14) 0.47733(8) 0.0308(3) Uani . . 1.000
    C C13 0.90248(10) -0.14431(15) 0.37815(8) 0.0317(4) Uani . . 1.000
    C C14 0.80417(10) -0.06296(15) 0.32991(8) 0.0279(3) Uani . . 1.000
    C C14A 0.72793(10) 0.00695(14) 0.37893(8) 0.0268(3) Uani . . 1.000
    C C15 0.62311(11) 0.09220(15) 0.33425(9) 0.0321(4) Uani . . 1.000
    C C16 0.55839(11) 0.16221(16) 0.38699(9) 0.0359(4) Uani . . 1.000
    C C17 0.59412(11) 0.15093(15) 0.48661(9) 0.0342(4) Uani . . 1.000
    C C18 0.69379(10) 0.06727(15) 0.53191(8) 0.0289(4) Uani . . 1.000
    C C18A 0.76407(10) -0.00955(14) 0.47940(8) 0.0267(3) Uani . . 1.000
    C C19 0.73096(11) 0.05847(17) 0.63863(9) 0.0350(4) Uani . . 1.000
    C C41 0.78389(12) 0.05745(16) -0.00728(9) 0.0370(4) Uani . . 1.000
    C C42 0.69031(14) 0.0203(2) -0.09740(9) 0.0514(5) Uani . . 1.000
    H H6A 0.97595 0.10527 0.28105 0.0515 Uiso . . 1.000
    H H6B 1.00988 0.06222 0.18563 0.0515 Uiso . . 1.000
    H H6C 0.94153 0.22637 0.19263 0.0515 Uiso . . 1.000
    H H12 0.99402 -0.21921 0.51019 0.0370 Uiso . . 1.000
    H H13 0.95383 -0.19059 0.34570 0.0380 Uiso . . 1.000
    H H15 0.59782 0.10056 0.26699 0.0385 Uiso . . 1.000
    H H16 0.48832 0.21932 0.35621 0.0431 Uiso . . 1.000
    H H17 0.54873 0.20176 0.52263 0.0410 Uiso . . 1.000
    H H42A 0.69885 0.09280 -0.14779 0.0771 Uiso . . 1.000
    H H42B 0.69863 -0.09168 -0.11590 0.0771 Uiso . . 1.000
    H H42C 0.61224 0.03535 -0.08746 0.0771 Uiso . . 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 C19 . . 1.3399(16) no
    F2 C19 . . 1.3339(17) no
    F3 C19 . . 1.3454(16) no
    O41 C41 . . 1.2160(19) no
    N1 N2 . . 1.3762(16) no
    N1 C5 . . 1.3553(16) no
    N1 C14 . . 1.4337(15) no
    N2 N3 . . 1.2986(14) no
    N3 C4 . . 1.3680(16) no
    N11 C12 . . 1.3172(16) no
    N11 C18A . . 1.3630(16) no
    C4 C5 . . 1.3800(16) no
    C4 C41 . . 1.4728(17) no
    C5 C6 . . 1.4876(17) no
    C12 C13 . . 1.4071(16) no
    C13 C14 . . 1.3570(17) no
    C14 C14A . . 1.4230(17) no
    C14A C15 . . 1.4158(18) no
    C14A C18A . . 1.4216(16) no
    C15 C16 . . 1.3601(19) no
    C16 C17 . . 1.4061(18) no
    C17 C18 . . 1.3667(18) no
    C18 C18A . . 1.4300(17) no
    C18 C19 . . 1.5047(17) no
    C41 C42 . . 1.4979(19) no
    C6 H6A . . 0.9800 no
    C6 H6B . . 0.9800 no
    C6 H6C . . 0.9800 no
    C12 H12 . . 0.9500 no
    C13 H13 . . 0.9500 no
    C15 H15 . . 0.9500 no
    C16 H16 . . 0.9500 no
    C17 H17 . . 0.9500 no
    C42 H42A . . 0.9800 no
    C42 H42B . . 0.9800 no
    C42 H42C . . 0.9800 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 C6 3.3366(15) . 4_455 no
    F2 N11 2.8876(13) . . no
    F3 N11 2.9431(13) . . no
    F3 C6 3.2730(15) . 3_756 no
    F1 H42A 2.5200 . 1_556 no
    F1 H6C 2.8300 . 4_455 no
    F1 H17 2.3100 . . no
    F2 H42A 2.7700 . 2_645 no
    F2 H16 2.8100 . 3_656 no
    F3 H42B 2.4800 . 2_655 no
    F3 H6B 2.8000 . 3_756 no
    F3 H13 2.6400 . 3_756 no
    O41 C6 3.0801(16) . . no
    O41 C17 3.1961(18) . 4_554 no
    O41 H6B 2.8900 . . no
    O41 H6C 2.9200 . . no
    O41 H17 2.4300 . 4_554 no
    N1 C15 3.4485(17) . 2_645 no
    N2 C15 3.1005(17) . . no
    N2 C6 3.3807(17) . 2_645 no
    N2 C15 3.4457(18) . 2_645 no
    N11 C41 3.3399(17) . 2_645 no
    N11 F3 2.9431(13) . . no
    N11 C13 3.3713(16) . 3_756 no
    N11 F2 2.8876(13) . . no
    N11 C12 3.2696(17) . 3_756 no
    N1 H15 2.6200 . . no
    N2 H15 2.5500 . . no
    N3 H12 2.6100 . 4_444 no
    N3 H42C 2.6300 . . no
    N11 H6A 2.9200 . 3_756 no
    C4 C12 3.5509(17) . 2_655 no
    C4 C16 3.4724(18) . 2_645 no
    C5 C16 3.4972(18) . 2_645 no
    C6 C13 3.4080(18) . . no
    C6 O41 3.0801(16) . . no
    C6 F1 3.3366(15) . 4_554 no
    C6 N2 3.3807(17) . 2_655 no
    C6 F3 3.2730(15) . 3_756 no
    C12 C4 3.5509(17) . 2_645 no
    C12 C12 3.1164(17) . 3_756 no
    C12 C41 3.5387(19) . 2_645 no
    C12 N11 3.2696(17) . 3_756 no
    C12 C13 3.5320(17) . 3_756 no
    C13 N11 3.3713(16) . 3_756 no
    C13 C6 3.4080(18) . . no
    C13 C12 3.5320(17) . 3_756 no
    C15 N2 3.4457(18) . 2_655 no
    C15 N1 3.4485(17) . 2_655 no
    C15 N2 3.1005(17) . . no
    C16 C4 3.4724(18) . 2_655 no
    C16 C5 3.4972(18) . 2_655 no
    C17 O41 3.1961(18) . 4_455 no
    C17 C17 3.4415(18) . 3_656 no
    C41 N11 3.3399(17) . 2_655 no
    C41 C12 3.5387(19) . 2_655 no
    C5 H13 3.1000 . . no
    C13 H15 3.0000 . 2_645 no
    C13 H6A 2.7900 . . no
    C14 H6A 2.7200 . . no
    C14A H6C 3.0600 . 2_645 no
    C19 H42B 3.0600 . 2_655 no
    H6A C13 2.7900 . . no
    H6A C14 2.7200 . . no
    H6A N11 2.9200 . 3_756 no
    H6B O41 2.8900 . . no
    H6B F3 2.8000 . 3_756 no
    H6C O41 2.9200 . . no
    H6C C14A 3.0600 . 2_655 no
    H6C F1 2.8300 . 4_554 no
    H12 N3 2.6100 . 4_545 no
    H13 C5 3.1000 . . no
    H13 H15 2.3500 . 2_645 no
    H13 F3 2.6400 . 3_756 no
    H15 N1 2.6200 . . no
    H15 N2 2.5500 . . no
    H15 C13 3.0000 . 2_655 no
    H15 H13 2.3500 . 2_655 no
    H16 F2 2.8100 . 3_656 no
    H17 F1 2.3100 . . no
    H17 O41 2.4300 . 4_455 no
    H42A F1 2.5200 . 1_554 no
    H42A F2 2.7700 . 2_655 no
    H42B F3 2.4800 . 2_645 no
    H42B C19 3.0600 . 2_645 no
    H42C N3 2.6300 . . 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 C5 . . . 111.28(9) no
    N2 N1 C14 . . . 118.75(10) no
    C5 N1 C14 . . . 129.97(11) no
    N1 N2 N3 . . . 106.72(10) no
    N2 N3 C4 . . . 109.29(10) no
    C12 N11 C18A . . . 117.30(10) no
    N3 C4 C5 . . . 109.33(10) no
    N3 C4 C41 . . . 121.81(11) no
    C5 C4 C41 . . . 128.87(11) no
    N1 C5 C4 . . . 103.39(10) no
    N1 C5 C6 . . . 124.93(10) no
    C4 C5 C6 . . . 131.69(11) no
    N11 C12 C13 . . . 124.27(11) no
    C12 C13 C14 . . . 118.49(11) no
    N1 C14 C13 . . . 120.45(11) no
    N1 C14 C14A . . . 119.02(10) no
    C13 C14 C14A . . . 120.53(11) no
    C14 C14A C15 . . . 124.28(11) no
    C14 C14A C18A . . . 115.87(11) no
    C15 C14A C18A . . . 119.83(11) no
    C14A C15 C16 . . . 120.44(12) no
    C15 C16 C17 . . . 120.68(12) no
    C16 C17 C18 . . . 120.38(12) no
    C17 C18 C18A . . . 120.93(11) no
    C17 C18 C19 . . . 119.39(11) no
    C18A C18 C19 . . . 119.67(11) no
    N11 C18A C14A . . . 123.45(11) no
    N11 C18A C18 . . . 118.84(10) no
    C14A C18A C18 . . . 117.71(11) no
    F1 C19 F2 . . . 106.37(10) no
    F1 C19 F3 . . . 105.70(10) no
    F1 C19 C18 . . . 111.55(11) no
    F2 C19 F3 . . . 106.55(10) no
    F2 C19 C18 . . . 113.82(11) no
    F3 C19 C18 . . . 112.30(11) no
    O41 C41 C4 . . . 119.73(12) no
    O41 C41 C42 . . . 122.08(12) no
    C4 C41 C42 . . . 118.19(12) no
    C5 C6 H6A . . . 109.00 no
    C5 C6 H6B . . . 109.00 no
    C5 C6 H6C . . . 109.00 no
    H6A C6 H6B . . . 109.00 no
    H6A C6 H6C . . . 109.00 no
    H6B C6 H6C . . . 109.00 no
    N11 C12 H12 . . . 118.00 no
    C13 C12 H12 . . . 118.00 no
    C12 C13 H13 . . . 121.00 no
    C14 C13 H13 . . . 121.00 no
    C14A C15 H15 . . . 120.00 no
    C16 C15 H15 . . . 120.00 no
    C15 C16 H16 . . . 120.00 no
    C17 C16 H16 . . . 120.00 no
    C16 C17 H17 . . . 120.00 no
    C18 C17 H17 . . . 120.00 no
    C41 C42 H42A . . . 109.00 no
    C41 C42 H42B . . . 109.00 no
    C41 C42 H42C . . . 109.00 no
    H42A C42 H42B . . . 109.00 no
    H42A C42 H42C . . . 109.00 no
    H42B C42 H42C . . . 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
    C5 N1 N2 N3 . . . . -0.27(14) no
    C14 N1 N2 N3 . . . . -179.85(11) no
    N2 N1 C5 C4 . . . . 0.37(13) no
    N2 N1 C5 C6 . . . . -179.34(11) no
    C14 N1 C5 C4 . . . . 179.89(12) no
    C14 N1 C5 C6 . . . . 0.2(2) no
    N2 N1 C14 C13 . . . . 116.76(13) no
    N2 N1 C14 C14A . . . . -63.17(15) no
    C5 N1 C14 C13 . . . . -62.72(18) no
    C5 N1 C14 C14A . . . . 117.34(14) no
    N1 N2 N3 C4 . . . . 0.04(13) no
    N2 N3 C4 C5 . . . . 0.19(14) no
    N2 N3 C4 C41 . . . . 179.89(12) no
    C18A N11 C12 C13 . . . . 1.42(18) no
    C12 N11 C18A C14A . . . . 1.48(18) no
    C12 N11 C18A C18 . . . . -178.05(11) no
    N3 C4 C5 N1 . . . . -0.34(13) no
    N3 C4 C5 C6 . . . . 179.35(12) no
    C41 C4 C5 N1 . . . . 179.97(12) no
    C41 C4 C5 C6 . . . . -0.3(2) no
    N3 C4 C41 O41 . . . . -177.86(13) no
    N3 C4 C41 C42 . . . . 2.76(19) no
    C5 C4 C41 O41 . . . . 1.8(2) no
    C5 C4 C41 C42 . . . . -177.60(13) no
    N11 C12 C13 C14 . . . . -2.36(19) no
    C12 C13 C14 N1 . . . . -179.56(11) no
    C12 C13 C14 C14A . . . . 0.38(18) no
    N1 C14 C14A C15 . . . . 0.63(18) no
    N1 C14 C14A C18A . . . . -177.90(11) no
    C13 C14 C14A C15 . . . . -179.30(12) no
    C13 C14 C14A C18A . . . . 2.17(17) no
    C14 C14A C15 C16 . . . . -176.69(12) no
    C18A C14A C15 C16 . . . . 1.79(19) no
    C14 C14A C18A N11 . . . . -3.21(17) no
    C14 C14A C18A C18 . . . . 176.32(11) no
    C15 C14A C18A N11 . . . . 178.19(11) no
    C15 C14A C18A C18 . . . . -2.28(17) no
    C14A C15 C16 C17 . . . . -0.2(2) no
    C15 C16 C17 C18 . . . . -0.9(2) no
    C16 C17 C18 C18A . . . . 0.36(19) no
    C16 C17 C18 C19 . . . . 179.32(12) no
    C17 C18 C18A N11 . . . . -179.22(12) no
    C17 C18 C18A C14A . . . . 1.23(18) no
    C19 C18 C18A N11 . . . . 1.82(17) no
    C19 C18 C18A C14A . . . . -177.73(11) no
    C17 C18 C19 F1 . . . . 1.58(17) no
    C17 C18 C19 F2 . . . . 121.95(13) no
    C17 C18 C19 F3 . . . . -116.87(13) no
    C18A C18 C19 F1 . . . . -179.45(11) no
    C18A C18 C19 F2 . . . . -59.08(16) no
    C18A C18 C19 F3 . . . . 62.10(16) 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
    C12 H12 N3 4_545 0.95 2.61 3.559(2) 173.00 yes
    C15 H15 N2 . 0.95 2.55 3.101(2) 117.00 yes
    C17 H17 F1 . 0.95 2.31 2.668(2) 102.00 yes
    C17 H17 O41 4_455 0.95 2.43 3.196(2) 138.00 yes
    C42 H42A F1 1_554 0.98 2.52 3.373(2) 146.00 yes
    C42 H42B F3 2_645 0.98 2.48 3.434(2) 165.00 yes
