#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/73/2227395.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227395
loop_
_publ_author_name
'Devarajegowda, H. C.'
'Jeyaseelan, S.'
'Sumangala, V.'
Bojapoojary
'Nayak, Suresh P.'
_publ_section_title
;
 1-{1-[2,8-Bis(trifluoromethyl)-4-quinolyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone
;
_journal_coeditor_code           DS2049
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2512
_journal_page_last               o2513
_journal_paper_doi               10.1107/S1600536810034926
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H10 F6 N4 O'
_chemical_formula_moiety         'C16 H10 F6 N4 O'
_chemical_formula_sum            'C16 H10 F6 N4 O'
_chemical_formula_weight         388.28
_chemical_melting_point          427
_chemical_name_systematic
;
1-{1-[2,8-Bis(trifluoromethyl)-4-quinolyl]-5-methyl-1H-1,2,3-triazol-
4-yl}ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.172(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.064(2)
_cell_length_b                   8.7275(13)
_cell_length_c                   27.468(4)
_cell_measurement_reflns_used    5923
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.49
_cell_volume                     3362.6(8)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23473
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         5923
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0690P)²+1.1626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                4754
_reflns_number_total             5923
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2049.cif
_cod_data_source_block           I
_cod_original_cell_volume        3362.6(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227395
_cod_database_fobs_code          2227395
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
F F1 0.62603(13) -0.2838(2) 0.18151(6) 0.0844(5) Uani d . 1 . .
F F2 0.75645(12) -0.3765(2) 0.16020(6) 0.0801(5) Uani d . 1 . .
F F3 0.62542(16) -0.4783(2) 0.13491(7) 0.1023(7) Uani d . 1 . .
F F4B 0.8238(11) 0.0406(9) 0.23119(18) 0.128(3) Uani d PD 0.77(3) A 2
F F4A 0.7910(14) 0.083(3) 0.2312(5) 0.078(5) Uani d PDU 0.23(3) A 1
F F5B 0.9284(8) 0.158(3) 0.1861(9) 0.094(6) Uani d PDU 0.23(4) A 2
F F5A 0.9304(3) 0.101(2) 0.1948(5) 0.135(3) Uani d PD 0.77(4) A 1
F F6 0.82879(16) 0.2748(2) 0.20693(7) 0.0989(6) Uani d D 1 A .
F F7B 0.2388(9) 0.1504(13) 0.27486(16) 0.134(5) Uani d PD 0.520(14) B 2
F F7A 0.1679(8) 0.0748(7) 0.2564(4) 0.121(4) Uani d PDU 0.480(14) B 1
F F8B 0.2743(9) 0.2284(13) 0.2066(6) 0.135(6) Uani d PDU 0.385(17) B 2
F F8A 0.2871(4) 0.2331(8) 0.2421(6) 0.150(4) Uani d PDU 0.615(17) B 1
F F9B 0.1555(9) 0.0653(10) 0.2269(7) 0.096(6) Uani d PDU 0.217(11) B 2
F F9A 0.1964(4) 0.1177(6) 0.19132(18) 0.128(2) Uani d PD 0.783(11) B 1
F F10 0.06252(14) 0.3249(2) 0.37351(6) 0.0909(6) Uani d . 1 . .
F F11 0.17217(12) 0.4920(3) 0.37357(6) 0.0939(6) Uani d . 1 . .
F F12 0.04672(15) 0.5362(3) 0.41025(6) 0.1034(7) Uani d . 1 . .
O O1B 0.8131(8) 0.499(5) -0.0850(17) 0.094(6) Uani d PD 0.40(13) C 2
O O1A 0.8059(15) 0.466(5) -0.0966(16) 0.088(6) Uani d PD 0.60(13) C 1
O O2 -0.05430(19) 0.9546(3) 0.05710(9) 0.0934(7) Uani d . 1 D 1
N N1 0.75116(13) -0.0489(2) 0.14556(6) 0.0459(4) Uani d . 1 . .
N N2 0.70539(13) 0.2637(2) 0.02946(7) 0.0448(4) Uani d . 1 . .
N N3 0.61525(14) 0.3219(2) 0.02063(8) 0.0568(5) Uani d . 1 . .
N N4 0.61674(15) 0.4042(2) -0.01854(8) 0.0576(5) Uani d . 1 . .
N N5 0.11417(13) 0.3718(2) 0.27600(7) 0.0504(5) Uani d . 1 . .
N N6 -0.00853(13) 0.5686(2) 0.14652(6) 0.0466(4) Uani d . 1 . .
N N7 -0.06553(16) 0.4771(2) 0.11648(7) 0.0602(6) Uani d . 1 . .
N N8 -0.09389(16) 0.5602(3) 0.07907(8) 0.0648(6) Uani d . 1 . .
C C1 0.6679(2) -0.3437(3) 0.14425(10) 0.0590(7) Uani d . 1 . .
C C2 0.66029(16) -0.2409(3) 0.10050(8) 0.0456(5) Uani d . 1 . .
C C3 0.61058(17) -0.2867(3) 0.05863(9) 0.0518(6) Uani d . 1 . .
H H3 0.5842 -0.3844 0.0568 0.062 Uiso calc R 1 . .
C C4 0.59872(17) -0.1888(3) 0.01827(8) 0.0527(6) Uani d . 1 . .
H H4 0.5662 -0.2234 -0.0103 0.063 Uiso calc R 1 . .
C C5 0.63381(16) -0.0448(3) 0.02028(8) 0.0469(5) Uani d . 1 . .
H H5 0.6243 0.0197 -0.0066 0.056 Uiso calc R 1 . .
C C6 0.68504(14) 0.0080(2) 0.06324(7) 0.0405(5) Uani d . 1 . .
C C7 0.70045(14) -0.0920(2) 0.10371(7) 0.0401(5) Uani d . 1 . .
C C8 0.72286(15) 0.1571(2) 0.06873(8) 0.0422(5) Uani d . 1 . .
C C9 0.77317(16) 0.1999(3) 0.11060(8) 0.0493(5) Uani d . 1 . .
H H9 0.7988 0.2978 0.1144 0.059 Uiso calc R 1 . .
C C10 0.78488(16) 0.0901(3) 0.14781(8) 0.0480(5) Uani d . 1 A .
C C11 0.8398(2) 0.1312(3) 0.19515(10) 0.0672(8) Uani d D 1 . .
C C12 0.76358(16) 0.3096(3) -0.00439(8) 0.0488(5) Uani d D 1 . .
C C13 0.70503(18) 0.4002(3) -0.03525(9) 0.0523(6) Uani d D 1 C .
C C14 0.7286(3) 0.4792(3) -0.07976(10) 0.0699(8) Uani d D 1 . .
C C15 0.6496(3) 0.5594(5) -0.10873(13) 0.1034(12) Uani d . 1 C .
H H15A 0.6740 0.6064 -0.1369 0.155 Uiso calc R 1 . .
H H15B 0.6230 0.6367 -0.0889 0.155 Uiso calc R 1 . .
H H15C 0.6010 0.4867 -0.1191 0.155 Uiso calc R 1 . .
C C16 0.86421(19) 0.2661(4) -0.00449(11) 0.0729(8) Uani d D 1 . .
H H16A 0.8809 0.2009 0.0230 0.109 Uiso calc R 1 . .
H H16B 0.9031 0.3566 -0.0023 0.109 Uiso calc R 1 . .
H H16C 0.8745 0.2124 -0.0341 0.109 Uiso calc R 1 . .
C C17 0.2014(2) 0.1926(3) 0.23226(11) 0.0745(8) Uani d D 1 . .
C C18 0.13305(17) 0.3238(3) 0.23277(9) 0.0523(6) Uani d . 1 B .
C C19 0.09522(17) 0.3874(3) 0.18863(9) 0.0514(6) Uani d . 1 . .
H H19 0.1123 0.3498 0.1588 0.062 Uiso calc R 1 B .
C C20 0.03335(15) 0.5047(2) 0.19089(8) 0.0431(5) Uani d . 1 B .
C C21 0.00741(15) 0.5608(3) 0.23647(8) 0.0443(5) Uani d . 1 . .
C C22 0.05239(15) 0.4897(3) 0.27825(8) 0.0442(5) Uani d . 1 B .
C C23 0.03100(17) 0.5448(3) 0.32524(8) 0.0526(6) Uani d . 1 . .
C C24 0.0786(2) 0.4748(4) 0.36993(10) 0.0670(7) Uani d . 1 B .
C C25 -0.03136(19) 0.6618(3) 0.32868(10) 0.0636(7) Uani d . 1 B .
H H25 -0.0440 0.6983 0.3593 0.076 Uiso calc R 1 . .
C C26 -0.07694(19) 0.7285(3) 0.28722(10) 0.0645(7) Uani d . 1 . .
H H26 -0.1201 0.8078 0.2906 0.077 Uiso calc R 1 B .
C C27 -0.05890(17) 0.6790(3) 0.24192(9) 0.0537(6) Uani d . 1 B .
H H27 -0.0904 0.7233 0.2145 0.064 Uiso calc R 1 . .
C C28 -0.00056(16) 0.7101(3) 0.12737(8) 0.0483(5) Uani d . 1 . .
C C29 -0.05686(17) 0.7031(3) 0.08470(8) 0.0521(6) Uani d . 1 D .
C C30 -0.07782(19) 0.8242(4) 0.04788(10) 0.0658(7) Uani d . 1 . .
C C31 -0.1272(2) 0.7785(5) 0.00060(11) 0.0913(11) Uani d . 1 D .
H H31A -0.1367 0.8671 -0.0199 0.137 Uiso calc R 1 . .
H H31B -0.1879 0.7340 0.0062 0.137 Uiso calc R 1 . .
H H31C -0.0891 0.7049 -0.0152 0.137 Uiso calc R 1 . .
C C32 0.0637(2) 0.8291(3) 0.14926(11) 0.0700(8) Uani d . 1 . .
H H32A 0.0917 0.7937 0.1801 0.105 Uiso calc R 1 . .
H H32B 0.0280 0.9210 0.1540 0.105 Uiso calc R 1 . .
H H32C 0.1131 0.8500 0.1279 0.105 Uiso calc R 1 . .
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'
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
C10 N1 C7 . . 117.63(19) ?
C12 N2 N3 . . 111.66(18) ?
C12 N2 C8 . . 129.43(18) ?
N3 N2 C8 . . 118.67(17) ?
N4 N3 N2 . . 106.37(18) ?
N3 N4 C13 . . 109.73(19) ?
C18 N5 C22 . . 117.40(19) ?
C28 N6 N7 . . 111.18(18) ?
C28 N6 C20 . . 130.48(19) ?
N7 N6 C20 . . 118.33(18) ?
N8 N7 N6 . . 106.56(19) ?
N7 N8 C29 . . 109.3(2) ?
F2 C1 F1 . . 106.9(2) ?
F2 C1 F3 . . 105.7(2) ?
F1 C1 F3 . . 106.1(2) ?
F2 C1 C2 . . 114.0(2) ?
F1 C1 C2 . . 111.9(2) ?
F3 C1 C2 . . 111.6(2) ?
C3 C2 C7 . . 120.0(2) ?
C3 C2 C1 . . 120.3(2) ?
C7 C2 C1 . . 119.6(2) ?
C2 C3 C4 . . 120.9(2) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C5 C4 C3 . . 120.9(2) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 120.0(2) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C8 C6 C5 . . 123.73(19) ?
C8 C6 C7 . . 116.70(18) ?
C5 C6 C7 . . 119.57(19) ?
N1 C7 C2 . . 119.19(19) ?
N1 C7 C6 . . 122.24(19) ?
C2 C7 C6 . . 118.56(19) ?
C9 C8 C6 . . 120.9(2) ?
C9 C8 N2 . . 120.6(2) ?
C6 C8 N2 . . 118.44(18) ?
C8 C9 C10 . . 117.1(2) ?
C8 C9 H9 . . 121.4 ?
C10 C9 H9 . . 121.4 ?
N1 C10 C9 . . 125.4(2) ?
N1 C10 C11 . . 115.1(2) ?
C9 C10 C11 . . 119.5(2) ?
F4B C11 F5A . . 96.2(11) ?
F4B C11 F6 . . 111.4(5) ?
F5A C11 F6 . . 109.1(8) ?
F4B C11 F5B . . 118.2(13) ?
F5A C11 F5B . . 24.2(9) ?
F6 C11 F5B . . 90.5(12) ?
F4B C11 F4A . . 26.3(8) ?
F5A C11 F4A . . 120.5(13) ?
F6 C11 F4A . . 92.3(11) ?
F5B C11 F4A . . 139.1(14) ?
F4B C11 C10 . . 114.0(4) ?
F5A C11 C10 . . 112.7(4) ?
F6 C11 C10 . . 112.3(2) ?
F5B C11 C10 . . 108.3(11) ?
F4A C11 C10 . . 108.2(8) ?
N2 C12 C13 . . 103.2(2) ?
N2 C12 C16 . . 124.1(2) ?
C13 C12 C16 . . 132.7(2) ?
N4 C13 C12 . . 109.0(2) ?
N4 C13 C14 . . 122.7(2) ?
C12 C13 C14 . . 128.3(2) ?
O1A C14 O1B . . 20.3(18) ?
O1A C14 C13 . . 122.5(9) ?
O1B C14 C13 . . 116.5(15) ?
O1A C14 C15 . . 119.4(12) ?
O1B C14 C15 . . 124.5(13) ?
C13 C14 C15 . . 117.5(3) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C12 C16 H16A . . 109.5 ?
C12 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C12 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
F8A C17 F9B . . 136.6(7) ?
F8A C17 F9A . . 108.5(6) ?
F9B C17 F9A . . 58.2(8) ?
F8A C17 F7B . . 64.5(8) ?
F9B C17 F7B . . 91.4(8) ?
F9A C17 F7B . . 129.0(4) ?
F8A C17 F8B . . 44.4(5) ?
F9B C17 F8B . . 123.0(11) ?
F9A C17 F8B . . 69.7(9) ?
F7B C17 F8B . . 105.5(9) ?
F8A C17 F7A . . 118.4(8) ?
F9B C17 F7A . . 36.5(8) ?
F9A C17 F7A . . 92.6(6) ?
F7B C17 F7A . . 57.8(5) ?
F8B C17 F7A . . 139.9(5) ?
F8A C17 C18 . . 112.7(3) ?
F9B C17 C18 . . 110.2(6) ?
F9A C17 C18 . . 113.5(3) ?
F7B C17 C18 . . 115.2(3) ?
F8B C17 C18 . . 110.4(4) ?
F7A C17 C18 . . 109.7(4) ?
N5 C18 C19 . . 124.8(2) ?
N5 C18 C17 . . 115.3(2) ?
C19 C18 C17 . . 119.9(2) ?
C20 C19 C18 . . 117.8(2) ?
C20 C19 H19 . . 121.1 ?
C18 C19 H19 . . 121.1 ?
C19 C20 C21 . . 120.8(2) ?
C19 C20 N6 . . 119.0(2) ?
C21 C20 N6 . . 120.17(19) ?
C27 C21 C22 . . 119.8(2) ?
C27 C21 C20 . . 124.3(2) ?
C22 C21 C20 . . 115.9(2) ?
N5 C22 C21 . . 123.3(2) ?
N5 C22 C23 . . 118.4(2) ?
C21 C22 C23 . . 118.3(2) ?
C25 C23 C22 . . 119.8(2) ?
C25 C23 C24 . . 120.5(2) ?
C22 C23 C24 . . 119.7(2) ?
F11 C24 F10 . . 106.2(3) ?
F11 C24 F12 . . 106.5(2) ?
F10 C24 F12 . . 105.3(2) ?
F11 C24 C23 . . 113.7(2) ?
F10 C24 C23 . . 113.3(2) ?
F12 C24 C23 . . 111.2(3) ?
C23 C25 C26 . . 121.3(2) ?
C23 C25 H25 . . 119.3 ?
C26 C25 H25 . . 119.3 ?
C27 C26 C25 . . 120.7(2) ?
C27 C26 H26 . . 119.7 ?
C25 C26 H26 . . 119.7 ?
C26 C27 C21 . . 120.0(2) ?
C26 C27 H27 . . 120.0 ?
C21 C27 H27 . . 120.0 ?
N6 C28 C29 . . 103.5(2) ?
N6 C28 C32 . . 123.4(2) ?
C29 C28 C32 . . 132.8(2) ?
N8 C29 C28 . . 109.4(2) ?
N8 C29 C30 . . 121.6(2) ?
C28 C29 C30 . . 129.0(3) ?
O2 C30 C29 . . 119.5(3) ?
O2 C30 C31 . . 122.8(3) ?
C29 C30 C31 . . 117.7(3) ?
C30 C31 H31A . . 109.5 ?
C30 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C30 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C28 C32 H32A . . 109.5 ?
C28 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C28 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
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
F1 C1 . 1.325(3) ?
F2 C1 . 1.321(3) ?
F3 C1 . 1.334(3) ?
F4B C11 . 1.300(4) ?
F4A C11 . 1.313(7) ?
F5B C11 . 1.309(8) ?
F5A C11 . 1.301(5) ?
F6 C11 . 1.306(3) ?
F7B C17 . 1.301(5) ?
F7A C17 . 1.328(5) ?
F8B C17 . 1.324(6) ?
F8A C17 . 1.267(5) ?
F9B C17 . 1.288(7) ?
F9A C17 . 1.298(4) ?
F10 C24 . 1.333(3) ?
F11 C24 . 1.321(3) ?
F12 C24 . 1.337(3) ?
O1B C14 . 1.220(9) ?
O1A C14 . 1.217(7) ?
O2 C30 . 1.207(4) ?
N1 C10 . 1.303(3) ?
N1 C7 . 1.361(3) ?
N2 C12 . 1.344(3) ?
N2 N3 . 1.371(3) ?
N2 C8 . 1.432(3) ?
N3 N4 . 1.295(3) ?
N4 C13 . 1.355(3) ?
N5 C18 . 1.304(3) ?
N5 C22 . 1.352(3) ?
N6 C28 . 1.350(3) ?
N6 N7 . 1.366(3) ?
N6 C20 . 1.428(3) ?
N7 N8 . 1.297(3) ?
N8 C29 . 1.356(3) ?
C1 C2 . 1.497(3) ?
C2 C3 . 1.362(3) ?
C2 C7 . 1.417(3) ?
C3 C4 . 1.400(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.350(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.414(3) ?
C5 H5 . 0.9300 ?
C6 C8 . 1.410(3) ?
C6 C7 . 1.418(3) ?
C8 C9 . 1.358(3) ?
C9 C10 . 1.402(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.507(3) ?
C12 C13 . 1.386(3) ?
C12 C16 . 1.465(3) ?
C13 C14 . 1.462(4) ?
C14 C15 . 1.493(4) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.496(4) ?
C18 C19 . 1.402(3) ?
C19 C20 . 1.348(3) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.417(3) ?
C21 C27 . 1.406(3) ?
C21 C22 . 1.413(3) ?
C22 C23 . 1.429(3) ?
C23 C25 . 1.354(4) ?
C23 C24 . 1.486(4) ?
C25 C26 . 1.393(4) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.358(3) ?
C26 H26 . 0.9300 ?
C27 H27 . 0.9300 ?
C28 C29 . 1.367(3) ?
C28 C32 . 1.475(4) ?
C29 C30 . 1.478(4) ?
C30 C31 . 1.482(4) ?
C31 H31A . 0.9600 ?
C31 H31B . 0.9600 ?
C31 H31C . 0.9600 ?
C32 H32A . 0.9600 ?
C32 H32B . 0.9600 ?
C32 H32C . 0.9600 ?
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
C3 H3 F3 . 0.93 2.33 2.677(3) 102 yes
C5 H5 F12 5_556 0.93 2.51 3.178(3) 129 yes
C9 H9 N7 1_655 0.93 2.47 3.312(4) 151 yes
C16 H16A O2 1_645 0.96 2.49 3.359(4) 150 yes
C25 H25 F12 . 0.93 2.31 2.659(3) 102 yes
C32 H32B F5A 1_465 0.96 2.41 3.324(14) 158 yes
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
C12 N2 N3 N4 . . . . -0.1(3) ?
C8 N2 N3 N4 . . . . -174.99(19) ?
N2 N3 N4 C13 . . . . 0.2(3) ?
C28 N6 N7 N8 . . . . -0.6(3) ?
C20 N6 N7 N8 . . . . -179.6(2) ?
N6 N7 N8 C29 . . . . -0.5(3) ?
F2 C1 C2 C3 . . . . 122.6(3) ?
F1 C1 C2 C3 . . . . -115.9(3) ?
F3 C1 C2 C3 . . . . 2.9(4) ?
F2 C1 C2 C7 . . . . -61.0(3) ?
F1 C1 C2 C7 . . . . 60.5(3) ?
F3 C1 C2 C7 . . . . 179.3(2) ?
C7 C2 C3 C4 . . . . 0.3(4) ?
C1 C2 C3 C4 . . . . 176.7(2) ?
C2 C3 C4 C5 . . . . -2.0(4) ?
C3 C4 C5 C6 . . . . 1.3(4) ?
C4 C5 C6 C8 . . . . -179.0(2) ?
C4 C5 C6 C7 . . . . 1.0(3) ?
C10 N1 C7 C2 . . . . -178.2(2) ?
C10 N1 C7 C6 . . . . 0.9(3) ?
C3 C2 C7 N1 . . . . -179.0(2) ?
C1 C2 C7 N1 . . . . 4.6(3) ?
C3 C2 C7 C6 . . . . 1.9(3) ?
C1 C2 C7 C6 . . . . -174.5(2) ?
C8 C6 C7 N1 . . . . -1.6(3) ?
C5 C6 C7 N1 . . . . 178.4(2) ?
C8 C6 C7 C2 . . . . 177.44(19) ?
C5 C6 C7 C2 . . . . -2.6(3) ?
C5 C6 C8 C9 . . . . -178.6(2) ?
C7 C6 C8 C9 . . . . 1.4(3) ?
C5 C6 C8 N2 . . . . 2.6(3) ?
C7 C6 C8 N2 . . . . -177.39(18) ?
C12 N2 C8 C9 . . . . 79.1(3) ?
N3 N2 C8 C9 . . . . -107.1(2) ?
C12 N2 C8 C6 . . . . -102.1(3) ?
N3 N2 C8 C6 . . . . 71.7(3) ?
C6 C8 C9 C10 . . . . -0.5(3) ?
N2 C8 C9 C10 . . . . 178.3(2) ?
C7 N1 C10 C9 . . . . 0.1(3) ?
C7 N1 C10 C11 . . . . 179.6(2) ?
C8 C9 C10 N1 . . . . -0.3(4) ?
C8 C9 C10 C11 . . . . -179.8(2) ?
N1 C10 C11 F4B . . . . -18.2(8) ?
C9 C10 C11 F4B . . . . 161.4(8) ?
N1 C10 C11 F5A . . . . 90.1(11) ?
C9 C10 C11 F5A . . . . -90.3(11) ?
N1 C10 C11 F6 . . . . -146.1(2) ?
C9 C10 C11 F6 . . . . 33.5(3) ?
N1 C10 C11 F5B . . . . 115.6(12) ?
C9 C10 C11 F5B . . . . -64.9(12) ?
N1 C10 C11 F4A . . . . -45.7(13) ?
C9 C10 C11 F4A . . . . 133.9(13) ?
N3 N2 C12 C13 . . . . 0.0(3) ?
C8 N2 C12 C13 . . . . 174.1(2) ?
N3 N2 C12 C16 . . . . 179.8(2) ?
C8 N2 C12 C16 . . . . -6.0(4) ?
N3 N4 C13 C12 . . . . -0.3(3) ?
N3 N4 C13 C14 . . . . 178.4(2) ?
N2 C12 C13 N4 . . . . 0.2(3) ?
C16 C12 C13 N4 . . . . -179.7(3) ?
N2 C12 C13 C14 . . . . -178.4(3) ?
C16 C12 C13 C14 . . . . 1.8(5) ?
N4 C13 C14 O1A . . . . -175(3) ?
C12 C13 C14 O1A . . . . 4(3) ?
N4 C13 C14 O1B . . . . 163(3) ?
C12 C13 C14 O1B . . . . -19(3) ?
N4 C13 C14 C15 . . . . -3.4(4) ?
C12 C13 C14 C15 . . . . 175.0(3) ?
C22 N5 C18 C19 . . . . 1.1(4) ?
C22 N5 C18 C17 . . . . -179.7(2) ?
F8A C17 C18 N5 . . . . -76.4(9) ?
F9B C17 C18 N5 . . . . 96.7(10) ?
F9A C17 C18 N5 . . . . 159.8(4) ?
F7B C17 C18 N5 . . . . -4.9(9) ?
F8B C17 C18 N5 . . . . -124.3(10) ?
F7A C17 C18 N5 . . . . 57.8(7) ?
F8A C17 C18 C19 . . . . 102.8(8) ?
F9B C17 C18 C19 . . . . -84.1(10) ?
F9A C17 C18 C19 . . . . -21.0(5) ?
F7B C17 C18 C19 . . . . 174.3(8) ?
F8B C17 C18 C19 . . . . 55.0(11) ?
F7A C17 C18 C19 . . . . -123.0(7) ?
N5 C18 C19 C20 . . . . -1.4(4) ?
C17 C18 C19 C20 . . . . 179.5(2) ?
C18 C19 C20 C21 . . . . -0.3(3) ?
C18 C19 C20 N6 . . . . -178.1(2) ?
C28 N6 C20 C19 . . . . -115.8(3) ?
N7 N6 C20 C19 . . . . 63.0(3) ?
C28 N6 C20 C21 . . . . 66.3(3) ?
N7 N6 C20 C21 . . . . -114.9(2) ?
C19 C20 C21 C27 . . . . -177.8(2) ?
N6 C20 C21 C27 . . . . 0.0(3) ?
C19 C20 C21 C22 . . . . 1.9(3) ?
N6 C20 C21 C22 . . . . 179.73(18) ?
C18 N5 C22 C21 . . . . 0.7(3) ?
C18 N5 C22 C23 . . . . -179.7(2) ?
C27 C21 C22 N5 . . . . 177.5(2) ?
C20 C21 C22 N5 . . . . -2.2(3) ?
C27 C21 C22 C23 . . . . -2.1(3) ?
C20 C21 C22 C23 . . . . 178.20(19) ?
N5 C22 C23 C25 . . . . -179.3(2) ?
C21 C22 C23 C25 . . . . 0.3(3) ?
N5 C22 C23 C24 . . . . 1.7(3) ?
C21 C22 C23 C24 . . . . -178.7(2) ?
C25 C23 C24 F11 . . . . -116.5(3) ?
C22 C23 C24 F11 . . . . 62.5(3) ?
C25 C23 C24 F10 . . . . 122.1(3) ?
C22 C23 C24 F10 . . . . -59.0(3) ?
C25 C23 C24 F12 . . . . 3.8(4) ?
C22 C23 C24 F12 . . . . -177.3(2) ?
C22 C23 C25 C26 . . . . 1.2(4) ?
C24 C23 C25 C26 . . . . -179.8(3) ?
C23 C25 C26 C27 . . . . -0.9(4) ?
C25 C26 C27 C21 . . . . -1.0(4) ?
C22 C21 C27 C26 . . . . 2.4(4) ?
C20 C21 C27 C26 . . . . -177.9(2) ?
N7 N6 C28 C29 . . . . 1.3(3) ?
C20 N6 C28 C29 . . . . -179.8(2) ?
N7 N6 C28 C32 . . . . -173.9(2) ?
C20 N6 C28 C32 . . . . 4.9(4) ?
N7 N8 C29 C28 . . . . 1.3(3) ?
N7 N8 C29 C30 . . . . -179.3(2) ?
N6 C28 C29 N8 . . . . -1.6(3) ?
C32 C28 C29 N8 . . . . 173.0(3) ?
N6 C28 C29 C30 . . . . 179.1(2) ?
C32 C28 C29 C30 . . . . -6.3(5) ?
N8 C29 C30 O2 . . . . 170.1(3) ?
C28 C29 C30 O2 . . . . -10.6(4) ?
N8 C29 C30 C31 . . . . -10.1(4) ?
C28 C29 C30 C31 . . . . 169.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079606
