#------------------------------------------------------------------------------
#$Date: 2026-06-05 21:25:31 +0200 (Fri 05 de Jun de 2026) $
#$Revision: 306457 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064356.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_7064356
loop_
_publ_author_name
'Panova, Elizaveta V.'
'Ganiev, Bakhtiyor Sh.'
'Avezov, Kuvondik G.'
'Umarov, Bako B.'
'Voronina, Julia K.'
'Safin, Damir A.'
_publ_section_title
;
 Synthesis and structural elucidation of a trifluoromethylated
 cyclopentene hydrazone: a combined X-ray and computational study
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7490
_journal_page_last               7504
_journal_paper_doi               10.1039/D6NJ00632A
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C14 H13 F3 N2 O2'
_chemical_formula_sum            'C14 H13 F3 N2 O2'
_chemical_formula_weight         298.26
_chemical_name_common
N'-(2-trifluoroacetylcyclopent-1-enyl)benzohydrazide
_chemical_name_systematic
'bezoylhydrazone 2-trifluoroacetylsiklopentanone'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-09-01
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-10-07 deposited with the CCDC.	2026-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                97.863(5)
_cell_angle_beta                 105.578(6)
_cell_angle_gamma                97.842(5)
_cell_formula_units_Z            4
_cell_length_a                   9.3763(6)
_cell_length_b                   11.8162(7)
_cell_length_c                   13.2214(9)
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.4810
_cell_measurement_theta_min      3.8250
_cell_volume                     1374.54(16)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22830
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.546
_diffrn_reflns_theta_min         3.529
_exptl_absorpt_coefficient_mu    1.081
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5637
_refine_ls_number_restraints     182
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0924P)²+0.0155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.2008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3139
_reflns_number_total             5637
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6nj00632a2.cif
_cod_data_source_block           1586402
_cod_depositor_comments          'Adding full bibliography for 7064356.cif.'
_cod_original_cell_volume        1374.55(16)
_cod_database_code               7064356
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F1A"-F2A" \\sim F1A"-F3A" \\sim F2A"-F3A" \\sim F2A'-F1A' \\sim F2A'-F3A'
\\sim F1A'-F3A' \\sim F2A-
 F1A \\sim F2A-F3A \\sim F1A-F3A
 with sigma of 0.04
 C3A-F1A" \\sim C3A-F2A" \\sim C3A-C2A \\sim C3A-F3A" \\sim C3A-F2A' \\sim
C3A-F1A' \\sim C3A-F3A' ~
 C3A-F2A \\sim C3A-F1A
 with sigma of 0.02
 F1B'-F3B' \\sim F1B'-F2B' \\sim F2B"-F3B" \\sim F2B"-F1B" \\sim F3B-F2B \\sim
F3B-F1B \\sim F2B-F1B ~
 F3B'-F2B' \\sim F3B"-F1B"
 with sigma of 0.04
 C3B-F1B' \\sim C3B-F2B" \\sim C3B-F3B \\sim C3B-F2B \\sim C3B-F3B' \\sim
C3B-F3B" \\sim C3B-F1B" ~
 C3B-F1B \\sim C3B-C2B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F2A) \\sim Ueq, Uanis(F2A') \\sim Ueq, Uanis(F2A") \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2B) \\sim Ueq, Uanis(F2B') \\sim Ueq, Uanis(F2B") \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2A') = Uanis(F2A) = Uanis(F2A")
Uanis(F3A') = Uanis(F3A) = Uanis(F3A")
Uanis(F1A') = Uanis(F1A) = Uanis(F1A")
Uanis(F3B) = Uanis(F3B") = Uanis(F3B')
Uanis(F1B") = Uanis(F1B') = Uanis(F1B)
Uanis(F2B") = Uanis(F2B') = Uanis(F2B)
4. Others
 1*[Sof(F1A)+Sof(F2A)+Sof(F3A)]+1*[Sof(F1A')+Sof(F2A')+Sof(F3A')]+1*[Sof(F1A")+
 Sof(F2A")+Sof(F3A")]=1 with esd of 0.000001
 1*[Sof(F1B)+Sof(F2B)+Sof(F3B)]+1*[Sof(F1B')+Sof(F2B')+Sof(F3B')]+1*[Sof(F1B")+
 Sof(F2B")+Sof(F3B")]=1 with esd of 0.000001
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
 Sof(F1A')=Sof(F2A')=Sof(F3A')=FVAR(2)
 Sof(F1A")=Sof(F2A")=Sof(F3A")=FVAR(3)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(4)
 Sof(F1B')=Sof(F2B')=Sof(F3B')=FVAR(5)
 Sof(F1B")=Sof(F2B")=Sof(F3B")=FVAR(6)
5.a Secondary CH2 refined with riding coordinates:
 C12A(H8A,H9A), C13A(H10A,H11A), C14A(H12A,H13A), C12B(H8B,H9B), C13B(H10B,
 H11B), C14B(H12B,H13B)
5.b Aromatic/amide H refined with riding coordinates:
 C5A(H3A), C6A(H4A), C7A(H5A), C8A(H6A), C9A(H7A), C5B(H3B), C6B(H4B),
 C7B(H5B), C8B(H6B), C9B(H7B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.2635(5) -0.3271(5) -0.1294(4) 0.0950(14) Uani 0.647(3) 1 d D . P A 1
F1A' F 0.2232(16) -0.3268(17) -0.0986(13) 0.0950(14) Uani 0.220(3) 1 d D . P A 2
F1A" F 0.327(2) -0.352(2) -0.1411(12) 0.0950(14) Uani 0.133(3) 1 d D . P A 3
O1A O 0.4803(2) 0.01322(19) 0.33682(18) 0.0651(6) Uani 1 1 d . . . . .
N1A N 0.6787(3) 0.0270(2) 0.2731(2) 0.0585(7) Uani 1 1 d . . . . .
H1A H 0.770(4) 0.052(3) 0.277(3) 0.066(10) Uiso 1 1 d . . . . .
C1A C 0.6037(3) 0.0658(2) 0.3404(2) 0.0517(7) Uani 1 1 d . . . . .
F2A F 0.2302(5) -0.4358(4) -0.0174(4) 0.097(2) Uani 0.647(3) 1 d D U P A 1
F2A' F 0.2937(19) -0.4606(14) 0.0006(15) 0.097(2) Uani 0.220(3) 1 d D U P A 2
F2A" F 0.1930(18) -0.394(2) -0.040(2) 0.097(2) Uani 0.133(3) 1 d D U P A 3
O2A O 0.3987(3) -0.2673(2) 0.1333(2) 0.0848(8) Uani 1 1 d . . . . .
N2A N 0.6113(3) -0.0760(2) 0.2022(2) 0.0621(7) Uani 1 1 d . . . . .
H2A H 0.544(4) -0.126(3) 0.225(3) 0.062(9) Uiso 1 1 d . . . . .
C2A C 0.4306(4) -0.2723(3) 0.0468(3) 0.0630(8) Uani 1 1 d D . . . .
F3A F 0.4206(9) -0.4372(6) -0.0803(5) 0.095(2) Uani 0.647(3) 1 d D . P A 1
F3A' F 0.407(3) -0.412(2) -0.110(2) 0.095(2) Uani 0.220(3) 1 d D . P A 2
F3A" F 0.393(3) -0.4674(14) -0.0319(18) 0.095(2) Uani 0.133(3) 1 d D . P A 3
C3A C 0.3370(4) -0.3687(3) -0.0421(3) 0.0763(10) Uani 1 1 d D . . . .
C4A C 0.6783(3) 0.1752(2) 0.4180(2) 0.0529(7) Uani 1 1 d . . . . .
C5A C 0.7703(4) 0.2623(3) 0.3925(3) 0.0652(8) Uani 1 1 d . . . . .
H3A H 0.7936 0.2510 0.3282 0.078 Uiso 1 1 calc R U . . .
C6A C 0.8272(4) 0.3665(3) 0.4640(4) 0.0818(11) Uani 1 1 d . . . . .
H4A H 0.8897 0.4250 0.4478 0.098 Uiso 1 1 calc R U . . .
C7A C 0.7916(5) 0.3836(3) 0.5585(3) 0.0851(12) Uani 1 1 d . . . . .
H5A H 0.8287 0.4541 0.6055 0.102 Uiso 1 1 calc R U . . .
C8A C 0.7022(5) 0.2976(3) 0.5839(3) 0.0792(10) Uani 1 1 d . . . . .
H6A H 0.6805 0.3091 0.6488 0.095 Uiso 1 1 calc R U . . .
C9A C 0.6435(4) 0.1929(3) 0.5133(3) 0.0650(8) Uani 1 1 d . . . . .
H7A H 0.5810 0.1350 0.5302 0.078 Uiso 1 1 calc R U . . .
C10A C 0.6224(3) -0.0972(2) 0.1038(2) 0.0538(7) Uani 1 1 d . . . . .
C11A C 0.5417(3) -0.1927(3) 0.0272(2) 0.0573(7) Uani 1 1 d . . . . .
C12A C 0.5866(5) -0.1914(3) -0.0736(3) 0.0803(11) Uani 1 1 d . . . . .
H8A H 0.5007 -0.1894 -0.1333 0.096 Uiso 1 1 calc R U . . .
H9A H 0.6293 -0.2593 -0.0904 0.096 Uiso 1 1 calc R U . . .
C13A C 0.7030(5) -0.0815(4) -0.0492(3) 0.0870(12) Uani 1 1 d . . . . .
H10A H 0.7976 -0.1007 -0.0562 0.104 Uiso 1 1 calc R U . . .
H11A H 0.6697 -0.0312 -0.0995 0.104 Uiso 1 1 calc R U . . .
C14A C 0.7252(4) -0.0196(3) 0.0630(3) 0.0702(9) Uani 1 1 d . . . . .
H12A H 0.8290 -0.0109 0.1061 0.084 Uiso 1 1 calc R U . . .
H13A H 0.6976 0.0566 0.0630 0.084 Uiso 1 1 calc R U . . .
F1B F 0.8110(7) -0.3391(7) 0.4736(6) 0.0933(19) Uani 0.473(3) 1 d D . P B 1
F1B' F 0.7545(14) -0.3194(13) 0.4734(9) 0.0933(19) Uani 0.304(3) 1 d D . P B 2
F1B" F 0.6684(16) -0.2696(11) 0.4342(11) 0.0933(19) Uani 0.223(3) 1 d D . P B 3
O1B O 0.9721(2) 0.13512(19) 0.26802(19) 0.0664(6) Uani 1 1 d . . . . .
N1B N 1.1879(3) 0.0749(2) 0.3326(2) 0.0568(6) Uani 1 1 d . . . . .
H1B H 1.285(4) 0.076(3) 0.341(3) 0.067(10) Uiso 1 1 d . . . . .
C1B C 1.1094(3) 0.1525(2) 0.2915(2) 0.0506(7) Uani 1 1 d . . . . .
F2B F 0.7279(10) -0.3931(6) 0.3105(6) 0.108(2) Uani 0.473(3) 1 d D U P B 1
F2B' F 0.8089(13) -0.4168(10) 0.3431(10) 0.108(2) Uani 0.304(3) 1 d D U P B 2
F2B" F 0.8080(14) -0.3932(9) 0.3987(12) 0.108(2) Uani 0.223(3) 1 d D U P B 3
O2B O 0.9189(3) -0.1218(2) 0.4525(2) 0.0837(8) Uani 1 1 d . . . . .
N2B N 1.1109(3) -0.0224(2) 0.3578(2) 0.0585(7) Uani 1 1 d . . . . .
H2B H 1.074(5) -0.008(4) 0.417(4) 0.101(14) Uiso 1 1 d . . . . .
C2B C 0.8855(4) -0.2032(3) 0.3766(3) 0.0604(8) Uani 1 1 d D . . . .
F3B F 0.6387(5) -0.2541(6) 0.3839(7) 0.1055(19) Uani 0.473(3) 1 d D . P B 1
F3B' F 0.6377(8) -0.3153(11) 0.2998(10) 0.1055(19) Uani 0.304(3) 1 d D . P B 2
F3B" F 0.6745(12) -0.3387(15) 0.2727(9) 0.1055(19) Uani 0.223(3) 1 d D . P B 3
C3B C 0.7631(5) -0.2993(3) 0.3806(3) 0.0856(12) Uani 1 1 d D . . . .
C4B C 1.1959(3) 0.2591(2) 0.2732(2) 0.0495(7) Uani 1 1 d . . . . .
C5B C 1.3443(3) 0.3041(3) 0.3292(3) 0.0582(7) Uani 1 1 d . . . . .
H3B H 1.3961 0.2667 0.3811 0.070 Uiso 1 1 calc R U . . .
C6B C 1.4163(4) 0.4044(3) 0.3086(3) 0.0662(9) Uani 1 1 d . . . . .
H4B H 1.5166 0.4337 0.3462 0.079 Uiso 1 1 calc R U . . .
C7B C 1.3408(4) 0.4609(3) 0.2332(3) 0.0691(9) Uani 1 1 d . . . . .
H5B H 1.3897 0.5287 0.2198 0.083 Uiso 1 1 calc R U . . .
C8B C 1.1934(4) 0.4176(3) 0.1774(3) 0.0718(9) Uani 1 1 d . . . . .
H6B H 1.1425 0.4557 0.1257 0.086 Uiso 1 1 calc R U . . .
C9B C 1.1199(4) 0.3173(3) 0.1976(3) 0.0638(8) Uani 1 1 d . . . . .
H7B H 1.0193 0.2888 0.1603 0.077 Uiso 1 1 calc R U . . .
C10B C 1.0541(3) -0.1194(2) 0.2847(2) 0.0525(7) Uani 1 1 d . . . . .
C11B C 0.9507(3) -0.2109(2) 0.2924(3) 0.0555(7) Uani 1 1 d . . . . .
C12B C 0.9207(4) -0.3080(3) 0.1973(3) 0.0746(10) Uani 1 1 d . . . . .
H8B H 0.9480 -0.3786 0.2204 0.090 Uiso 1 1 calc R U . . .
H9B H 0.8153 -0.3239 0.1561 0.090 Uiso 1 1 calc R U . . .
C13B C 1.0185(6) -0.2633(4) 0.1324(4) 0.1038(16) Uani 1 1 d . . . . .
H10B H 0.9565 -0.2613 0.0612 0.125 Uiso 1 1 calc R U . . .
H11B H 1.0893 -0.3146 0.1261 0.125 Uiso 1 1 calc R U . . .
C14B C 1.1029(4) -0.1425(3) 0.1868(3) 0.0687(9) Uani 1 1 d . . . . .
H12B H 1.2108 -0.1396 0.2050 0.082 Uiso 1 1 calc R U . . .
H13B H 1.0761 -0.0862 0.1413 0.082 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A H1A 126(2) . . ?
C1A N1A N2A 116.9(2) . . ?
N2A N1A H1A 116(2) . . ?
O1A C1A N1A 121.0(3) . . ?
O1A C1A C4A 122.3(3) . . ?
N1A C1A C4A 116.7(2) . . ?
N1A N2A H2A 115(2) . . ?
C10A N2A N1A 123.4(2) . . ?
C10A N2A H2A 121.2(19) . . ?
O2A C2A C3A 116.0(3) . . ?
O2A C2A C11A 124.9(3) . . ?
C11A C2A C3A 119.1(3) . . ?
F1A C3A C2A 111.8(4) . . ?
F1A' C3A F2A' 113.8(10) . . ?
F1A' C3A C2A 107.4(9) . . ?
F1A' C3A F3A' 106.9(13) . . ?
F1A" C3A F2A" 104.7(13) . . ?
F1A" C3A C2A 116.6(12) . . ?
F1A" C3A F3A" 106.4(13) . . ?
F2A C3A F1A 105.4(4) . . ?
F2A C3A C2A 114.7(4) . . ?
F2A C3A F3A 108.2(5) . . ?
F2A' C3A C2A 108.9(9) . . ?
F2A" C3A C2A 112.8(12) . . ?
F2A" C3A F3A" 105.9(12) . . ?
F3A C3A F1A 103.4(4) . . ?
F3A C3A C2A 112.5(5) . . ?
F3A' C3A F2A' 103.9(12) . . ?
F3A' C3A C2A 116.1(14) . . ?
F3A" C3A C2A 109.7(10) . . ?
C5A C4A C1A 121.5(3) . . ?
C9A C4A C1A 118.3(3) . . ?
C9A C4A C5A 120.0(3) . . ?
C4A C5A H3A 120.3 . . ?
C6A C5A C4A 119.3(3) . . ?
C6A C5A H3A 120.3 . . ?
C5A C6A H4A 119.8 . . ?
C7A C6A C5A 120.3(4) . . ?
C7A C6A H4A 119.8 . . ?
C6A C7A H5A 119.8 . . ?
C8A C7A C6A 120.4(3) . . ?
C8A C7A H5A 119.8 . . ?
C7A C8A H6A 119.9 . . ?
C7A C8A C9A 120.2(4) . . ?
C9A C8A H6A 119.9 . . ?
C4A C9A C8A 119.8(3) . . ?
C4A C9A H7A 120.1 . . ?
C8A C9A H7A 120.1 . . ?
N2A C10A C11A 124.5(3) . . ?
N2A C10A C14A 123.3(3) . . ?
C11A C10A C14A 112.1(3) . . ?
C2A C11A C12A 128.5(3) . . ?
C10A C11A C2A 121.2(3) . . ?
C10A C11A C12A 110.3(3) . . ?
C11A C12A H8A 110.9 . . ?
C11A C12A H9A 110.9 . . ?
C11A C12A C13A 104.3(3) . . ?
H8A C12A H9A 108.9 . . ?
C13A C12A H8A 110.9 . . ?
C13A C12A H9A 110.9 . . ?
C12A C13A H10A 109.8 . . ?
C12A C13A H11A 109.8 . . ?
H10A C13A H11A 108.2 . . ?
C14A C13A C12A 109.5(3) . . ?
C14A C13A H10A 109.8 . . ?
C14A C13A H11A 109.8 . . ?
C10A C14A C13A 103.7(3) . . ?
C10A C14A H12A 111.0 . . ?
C10A C14A H13A 111.0 . . ?
C13A C14A H12A 111.0 . . ?
C13A C14A H13A 111.0 . . ?
H12A C14A H13A 109.0 . . ?
C1B N1B H1B 125(2) . . ?
C1B N1B N2B 118.6(2) . . ?
N2B N1B H1B 116(2) . . ?
O1B C1B N1B 121.1(3) . . ?
O1B C1B C4B 121.6(3) . . ?
N1B C1B C4B 117.2(2) . . ?
N1B N2B H2B 116(3) . . ?
C10B N2B N1B 120.3(3) . . ?
C10B N2B H2B 121(3) . . ?
O2B C2B C3B 113.5(3) . . ?
O2B C2B C11B 125.4(3) . . ?
C11B C2B C3B 121.1(3) . . ?
F1B C3B C2B 108.2(4) . . ?
F1B' C3B F2B' 97.0(8) . . ?
F1B' C3B C2B 118.7(7) . . ?
F1B' C3B F3B' 119.5(7) . . ?
F1B" C3B C2B 116.9(6) . . ?
F1B" C3B F3B" 106.0(9) . . ?
F2B C3B F1B 102.3(6) . . ?
F2B C3B C2B 119.0(4) . . ?
F2B C3B F3B 110.6(5) . . ?
F2B" C3B F1B" 113.7(8) . . ?
F2B" C3B C2B 114.3(6) . . ?
F2B" C3B F3B" 98.3(9) . . ?
C2B C3B F2B' 106.6(5) . . ?
F3B C3B F1B 106.9(5) . . ?
F3B C3B C2B 109.0(4) . . ?
F3B' C3B F2B' 94.8(7) . . ?
F3B' C3B C2B 113.9(5) . . ?
F3B" C3B C2B 105.0(6) . . ?
C5B C4B C1B 123.8(3) . . ?
C5B C4B C9B 119.0(3) . . ?
C9B C4B C1B 117.2(3) . . ?
C4B C5B H3B 119.8 . . ?
C6B C5B C4B 120.3(3) . . ?
C6B C5B H3B 119.8 . . ?
C5B C6B H4B 119.8 . . ?
C7B C6B C5B 120.4(3) . . ?
C7B C6B H4B 119.8 . . ?
C6B C7B H5B 120.0 . . ?
C8B C7B C6B 120.0(3) . . ?
C8B C7B H5B 120.0 . . ?
C7B C8B H6B 119.9 . . ?
C7B C8B C9B 120.2(4) . . ?
C9B C8B H6B 119.9 . . ?
C4B C9B H7B 119.9 . . ?
C8B C9B C4B 120.2(3) . . ?
C8B C9B H7B 119.9 . . ?
N2B C10B C11B 125.0(3) . . ?
N2B C10B C14B 122.4(3) . . ?
C11B C10B C14B 112.5(3) . . ?
C2B C11B C12B 129.5(3) . . ?
C10B C11B C2B 121.0(3) . . ?
C10B C11B C12B 109.5(3) . . ?
C11B C12B H8B 110.8 . . ?
C11B C12B H9B 110.8 . . ?
H8B C12B H9B 108.9 . . ?
C13B C12B C11B 104.7(3) . . ?
C13B C12B H8B 110.8 . . ?
C13B C12B H9B 110.8 . . ?
C12B C13B H10B 109.9 . . ?
C12B C13B H11B 109.9 . . ?
C12B C13B C14B 109.1(3) . . ?
H10B C13B H11B 108.3 . . ?
C14B C13B H10B 109.9 . . ?
C14B C13B H11B 109.9 . . ?
C10B C14B C13B 104.2(3) . . ?
C10B C14B H12B 110.9 . . ?
C10B C14B H13B 110.9 . . ?
C13B C14B H12B 110.9 . . ?
C13B C14B H13B 110.9 . . ?
H12B C14B H13B 108.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C3A 1.367(6) . ?
F1A' C3A 1.325(12) . ?
F1A" C3A 1.330(13) . ?
O1A C1A 1.222(3) . ?
N1A H1A 0.85(3) . ?
N1A C1A 1.345(4) . ?
N1A N2A 1.385(3) . ?
C1A C4A 1.489(4) . ?
F2A C3A 1.329(5) . ?
F2A' C3A 1.353(12) . ?
F2A" C3A 1.349(13) . ?
O2A C2A 1.253(4) . ?
N2A H2A 0.94(3) . ?
N2A C10A 1.326(4) . ?
C2A C3A 1.502(5) . ?
C2A C11A 1.407(4) . ?
F3A C3A 1.342(7) . ?
F3A' C3A 1.340(13) . ?
F3A" C3A 1.350(12) . ?
C4A C5A 1.388(4) . ?
C4A C9A 1.381(4) . ?
C5A H3A 0.9300 . ?
C5A C6A 1.387(5) . ?
C6A H4A 0.9300 . ?
C6A C7A 1.374(6) . ?
C7A H5A 0.9300 . ?
C7A C8A 1.364(6) . ?
C8A H6A 0.9300 . ?
C8A C9A 1.388(5) . ?
C9A H7A 0.9300 . ?
C10A C11A 1.384(4) . ?
C10A C14A 1.495(4) . ?
C11A C12A 1.503(4) . ?
C12A H8A 0.9700 . ?
C12A H9A 0.9700 . ?
C12A C13A 1.513(5) . ?
C13A H10A 0.9700 . ?
C13A H11A 0.9700 . ?
C13A C14A 1.508(5) . ?
C14A H12A 0.9700 . ?
C14A H13A 0.9700 . ?
F1B C3B 1.362(8) . ?
F1B' C3B 1.301(10) . ?
F1B" C3B 1.330(10) . ?
O1B C1B 1.222(3) . ?
N1B H1B 0.89(3) . ?
N1B C1B 1.335(4) . ?
N1B N2B 1.400(3) . ?
C1B C4B 1.488(4) . ?
F2B C3B 1.285(7) . ?
F2B' C3B 1.564(14) . ?
F2B" C3B 1.270(11) . ?
O2B C2B 1.231(4) . ?
N2B H2B 0.94(4) . ?
N2B C10B 1.336(4) . ?
C2B C3B 1.518(4) . ?
C2B C11B 1.404(4) . ?
F3B C3B 1.356(7) . ?
F3B' C3B 1.330(9) . ?
F3B" C3B 1.421(11) . ?
C4B C5B 1.380(4) . ?
C4B C9B 1.386(4) . ?
C5B H3B 0.9300 . ?
C5B C6B 1.379(4) . ?
C6B H4B 0.9300 . ?
C6B C7B 1.369(5) . ?
C7B H5B 0.9300 . ?
C7B C8B 1.368(5) . ?
C8B H6B 0.9300 . ?
C8B C9B 1.384(5) . ?
C9B H7B 0.9300 . ?
C10B C11B 1.384(4) . ?
C10B C14B 1.488(4) . ?
C11B C12B 1.518(4) . ?
C12B H8B 0.9700 . ?
C12B H9B 0.9700 . ?
C12B C13B 1.506(5) . ?
C13B H10B 0.9700 . ?
C13B H11B 0.9700 . ?
C13B C14B 1.513(5) . ?
C14B H12B 0.9700 . ?
C14B H13B 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O1B 0.85(3) 2.05(4) 2.892(3) 169(3) .
N2A H2A O1A 0.94(3) 2.31(3) 2.608(3) 98(2) .
N2A H2A O2A 0.94(3) 2.01(3) 2.672(3) 126(3) .
N1B H1B O1A 0.89(3) 2.08(4) 2.920(3) 158(3) 1_655
N2B H2B O2B 0.94(4) 2.13(4) 2.934(4) 143(4) 2_756
N2B H2B O2B 0.94(4) 2.04(4) 2.687(3) 125(4) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C4A C5A -147.3(3) . . . . ?
O1A C1A C4A C9A 27.1(5) . . . . ?
N1A C1A C4A C5A 32.5(4) . . . . ?
N1A C1A C4A C9A -153.2(3) . . . . ?
N1A N2A C10A C11A -171.7(3) . . . . ?
N1A N2A C10A C14A 8.5(5) . . . . ?
C1A N1A N2A C10A 145.2(3) . . . . ?
C1A C4A C5A C6A 174.7(3) . . . . ?
C1A C4A C9A C8A -175.2(3) . . . . ?
O2A C2A C3A F1A 120.7(4) . . . . ?
O2A C2A C3A F1A' 92.6(8) . . . . ?
O2A C2A C3A F1A" 155.3(13) . . . . ?
O2A C2A C3A F2A 0.9(6) . . . . ?
O2A C2A C3A F2A' -31.1(10) . . . . ?
O2A C2A C3A F2A" 34.1(13) . . . . ?
O2A C2A C3A F3A -123.4(4) . . . . ?
O2A C2A C3A F3A' -147.9(12) . . . . ?
O2A C2A C3A F3A" -83.6(12) . . . . ?
O2A C2A C11A C10A -2.7(6) . . . . ?
O2A C2A C11A C12A -179.6(4) . . . . ?
N2A N1A C1A O1A -1.5(5) . . . . ?
N2A N1A C1A C4A 178.7(3) . . . . ?
N2A C10A C11A C2A 4.8(5) . . . . ?
N2A C10A C11A C12A -177.8(3) . . . . ?
N2A C10A C14A C13A 177.7(3) . . . . ?
C2A C11A C12A C13A 176.1(4) . . . . ?
C3A C2A C11A C10A 174.8(3) . . . . ?
C3A C2A C11A C12A -2.1(6) . . . . ?
C4A C5A C6A C7A -0.6(6) . . . . ?
C5A C4A C9A C8A -0.7(5) . . . . ?
C5A C6A C7A C8A 1.1(6) . . . . ?
C6A C7A C8A C9A -1.5(6) . . . . ?
C7A C8A C9A C4A 1.3(6) . . . . ?
C9A C4A C5A C6A 0.4(5) . . . . ?
C10A C11A C12A C13A -1.0(4) . . . . ?
C11A C2A C3A F1A -56.9(5) . . . . ?
C11A C2A C3A F1A' -85.1(8) . . . . ?
C11A C2A C3A F1A" -22.3(13) . . . . ?
C11A C2A C3A F2A -176.8(4) . . . . ?
C11A C2A C3A F2A' 151.3(9) . . . . ?
C11A C2A C3A F2A" -143.6(12) . . . . ?
C11A C2A C3A F3A 59.0(5) . . . . ?
C11A C2A C3A F3A' 34.5(12) . . . . ?
C11A C2A C3A F3A" 98.7(12) . . . . ?
C11A C10A C14A C13A -2.1(4) . . . . ?
C11A C12A C13A C14A -0.3(5) . . . . ?
C12A C13A C14A C10A 1.4(5) . . . . ?
C14A C10A C11A C2A -175.4(3) . . . . ?
C14A C10A C11A C12A 2.0(4) . . . . ?
O1B C1B C4B C5B 156.2(3) . . . . ?
O1B C1B C4B C9B -21.8(4) . . . . ?
N1B C1B C4B C5B -25.3(4) . . . . ?
N1B C1B C4B C9B 156.8(3) . . . . ?
N1B N2B C10B C11B -165.7(3) . . . . ?
N1B N2B C10B C14B 17.2(5) . . . . ?
C1B N1B N2B C10B 89.3(3) . . . . ?
C1B C4B C5B C6B -179.1(3) . . . . ?
C1B C4B C9B C8B 179.4(3) . . . . ?
O2B C2B C3B F1B -58.1(6) . . . . ?
O2B C2B C3B F1B' -31.9(9) . . . . ?
O2B C2B C3B F1B" 25.7(9) . . . . ?
O2B C2B C3B F2B -174.2(6) . . . . ?
O2B C2B C3B F2B' -139.9(6) . . . . ?
O2B C2B C3B F2B" -110.6(9) . . . . ?
O2B C2B C3B F3B 57.8(6) . . . . ?
O2B C2B C3B F3B' 117.0(8) . . . . ?
O2B C2B C3B F3B" 142.8(8) . . . . ?
O2B C2B C11B C10B -4.8(6) . . . . ?
O2B C2B C11B C12B 178.2(4) . . . . ?
N2B N1B C1B O1B -5.9(4) . . . . ?
N2B N1B C1B C4B 175.6(2) . . . . ?
N2B C10B C11B C2B 5.9(5) . . . . ?
N2B C10B C11B C12B -176.6(3) . . . . ?
N2B C10B C14B C13B 176.3(3) . . . . ?
C2B C11B C12B C13B 177.2(4) . . . . ?
C3B C2B C11B C10B 175.1(3) . . . . ?
C3B C2B C11B C12B -1.8(6) . . . . ?
C4B C5B C6B C7B 0.7(5) . . . . ?
C5B C4B C9B C8B 1.4(5) . . . . ?
C5B C6B C7B C8B -0.3(5) . . . . ?
C6B C7B C8B C9B 0.5(5) . . . . ?
C7B C8B C9B C4B -1.1(5) . . . . ?
C9B C4B C5B C6B -1.2(5) . . . . ?
C10B C11B C12B C13B 0.0(4) . . . . ?
C11B C2B C3B F1B 121.9(5) . . . . ?
C11B C2B C3B F1B' 148.2(8) . . . . ?
C11B C2B C3B F1B" -154.3(8) . . . . ?
C11B C2B C3B F2B 5.8(8) . . . . ?
C11B C2B C3B F2B' 40.1(7) . . . . ?
C11B C2B C3B F2B" 69.4(9) . . . . ?
C11B C2B C3B F3B -122.2(5) . . . . ?
C11B C2B C3B F3B' -63.0(8) . . . . ?
C11B C2B C3B F3B" -37.1(9) . . . . ?
C11B C10B C14B C13B -1.0(4) . . . . ?
C11B C12B C13B C14B -0.6(5) . . . . ?
C12B C13B C14B C10B 1.0(5) . . . . ?
C14B C10B C11B C2B -176.8(3) . . . . ?
C14B C10B C11B C12B 0.7(4) . . . . ?
