#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/69/2226901.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226901
loop_
_publ_author_name
'Shahani, Tara'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Sarveswari, S.'
_publ_section_title
;
 3-Ethyl-4-phenoxy-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-ol
;
_journal_coeditor_code           HB5540
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1937
_journal_page_last               o1938
_journal_paper_doi               10.1107/S1600536810025948
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H13 F3 N2 O2'
_chemical_formula_moiety         'C13 H13 F3 N2 O2'
_chemical_formula_sum            'C13 H13 F3 N2 O2'
_chemical_formula_weight         286.25
_chemical_name_systematic
;
3-Ethyl-4-phenoxy-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-ol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 113.889(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.3490(18)
_cell_length_b                   14.712(3)
_cell_length_c                   20.319(4)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.08
_cell_measurement_theta_min      2.50
_cell_volume                     2555.3(9)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            35406
_diffrn_reflns_theta_full        33.10
_diffrn_reflns_theta_max         33.10
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.553
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         9653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0895P)²+0.5995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1563
_reflns_number_gt                7544
_reflns_number_total             9653
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5540.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226901
_cod_database_fobs_code          2226901
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'
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 F1A 0.31537(13) 0.95145(9) 0.55763(5) 0.0481(3) Uani d . 1 . .
F F2A 0.30166(11) 1.01373(6) 0.45960(6) 0.0391(2) Uani d . 1 . .
F F3A 0.39030(10) 0.87810(6) 0.48585(6) 0.0382(2) Uani d . 1 . .
O O1A -0.02252(9) 0.65761(6) 0.57549(4) 0.01824(16) Uani d . 1 . .
O O2A -0.02449(11) 0.86757(6) 0.54830(5) 0.01993(16) Uani d . 1 . .
H H1OA -0.0368 0.8517 0.5843 0.030 Uiso calc R 1 . .
N N1A 0.14431(11) 0.73591(6) 0.45565(5) 0.01659(17) Uani d . 1 . .
N N2A 0.09635(11) 0.81452(6) 0.47642(5) 0.01577(17) Uani d . 1 . .
C C1A 0.24276(14) 0.64218(8) 0.66821(6) 0.0199(2) Uani d . 1 . .
H H1AA 0.2857 0.6722 0.6402 0.024 Uiso calc R 1 . .
C C2A 0.33808(16) 0.61131(9) 0.73676(7) 0.0260(2) Uani d . 1 . .
H H2AA 0.4452 0.6223 0.7551 0.031 Uiso calc R 1 . .
C C3A 0.27568(18) 0.56449(9) 0.77815(7) 0.0292(3) Uani d . 1 . .
H H3AA 0.3405 0.5438 0.8238 0.035 Uiso calc R 1 . .
C C4A 0.11638(18) 0.54869(9) 0.75105(7) 0.0267(3) Uani d . 1 . .
H H4AA 0.0744 0.5166 0.7785 0.032 Uiso calc R 1 . .
C C5A 0.01825(15) 0.58036(8) 0.68319(6) 0.0212(2) Uani d . 1 . .
H H5AA -0.0890 0.5702 0.6654 0.025 Uiso calc R 1 . .
C C6A 0.08262(13) 0.62747(7) 0.64225(6) 0.01685(19) Uani d . 1 . .
C C7A 0.03786(12) 0.70534(7) 0.53426(6) 0.01559(18) Uani d . 1 . .
C C8A 0.10829(12) 0.66915(7) 0.49077(6) 0.01611(18) Uani d . 1 . .
C C9A 0.03091(12) 0.79864(7) 0.52395(5) 0.01559(18) Uani d . 1 . .
C C10A 0.11837(13) 0.90055(7) 0.44853(6) 0.01736(19) Uani d . 1 . .
H H10A 0.0446 0.9442 0.4525 0.021 Uiso calc R 1 . .
H H10B 0.0972 0.8940 0.3979 0.021 Uiso calc R 1 . .
C C11A 0.28240(15) 0.93581(9) 0.48839(7) 0.0248(2) Uani d . 1 . .
C C12A 0.13741(14) 0.57127(8) 0.48058(6) 0.0201(2) Uani d . 1 . .
H H12A 0.0530 0.5494 0.4372 0.024 Uiso calc R 1 . .
H H12B 0.1344 0.5368 0.5207 0.024 Uiso calc R 1 . .
C C13A 0.29193(16) 0.55208(9) 0.47496(9) 0.0284(3) Uani d . 1 . .
H H13A 0.3039 0.4877 0.4713 0.043 Uiso calc R 1 . .
H H13B 0.3765 0.5749 0.5171 0.043 Uiso calc R 1 . .
H H13C 0.2928 0.5816 0.4330 0.043 Uiso calc R 1 . .
F F1B 1.40543(10) 0.97140(6) 0.72206(5) 0.0347(2) Uani d . 1 . .
F F2B 1.29257(11) 0.98298(6) 0.79574(5) 0.0353(2) Uani d . 1 . .
F F3B 1.15899(10) 0.99932(6) 0.68199(5) 0.0337(2) Uani d . 1 . .
O O1B 0.86609(10) 0.71693(6) 0.80232(5) 0.01864(16) Uani d . 1 . .
O O2B 1.21261(10) 0.76971(6) 0.84486(4) 0.01944(16) Uani d . 1 . .
H H1OB 1.1880 0.7673 0.8792 0.029 Uiso calc R 1 . .
N N1B 0.96106(11) 0.83472(7) 0.67117(5) 0.01796(18) Uani d . 1 . .
N N2B 1.10254(11) 0.82572(7) 0.72879(5) 0.01590(17) Uani d . 1 . .
C C1B 0.75881(14) 0.85277(8) 0.83482(6) 0.0203(2) Uani d . 1 . .
H H1BA 0.8011 0.8909 0.8108 0.024 Uiso calc R 1 . .
C C2B 0.67177(15) 0.88829(9) 0.87052(7) 0.0243(2) Uani d . 1 . .
H H2BA 0.6560 0.9507 0.8703 0.029 Uiso calc R 1 . .
C C3B 0.60848(15) 0.83187(10) 0.90634(7) 0.0265(2) Uani d . 1 . .
H H3BA 0.5508 0.8563 0.9301 0.032 Uiso calc R 1 . .
C C4B 0.63163(15) 0.73870(10) 0.90657(7) 0.0250(2) Uani d . 1 . .
H H4BA 0.5890 0.7006 0.9304 0.030 Uiso calc R 1 . .
C C5B 0.71822(14) 0.70211(8) 0.87132(6) 0.0198(2) Uani d . 1 . .
H H5BA 0.7339 0.6397 0.8715 0.024 Uiso calc R 1 . .
C C6B 0.78125(12) 0.75984(8) 0.83571(6) 0.01636(19) Uani d . 1 . .
C C7B 0.92916(13) 0.76861(7) 0.76383(6) 0.01631(19) Uani d . 1 . .
C C8B 0.85532(13) 0.80022(8) 0.69294(6) 0.0185(2) Uani d . 1 . .
C C9B 1.08731(13) 0.78561(7) 0.78566(6) 0.01529(18) Uani d . 1 . .
C C10B 1.24605(13) 0.85110(7) 0.72379(6) 0.01700(19) Uani d . 1 . .
H H10C 1.2429 0.8313 0.6777 0.020 Uiso calc R 1 . .
H H10D 1.3323 0.8200 0.7612 0.020 Uiso calc R 1 . .
C C11B 1.27517(14) 0.95189(8) 0.73120(7) 0.0229(2) Uani d . 1 . .
C C12B 0.68516(15) 0.80124(9) 0.64426(7) 0.0249(2) Uani d . 1 . .
H H12C 0.6700 0.8390 0.6028 0.030 Uiso calc R 1 . .
H H12D 0.6277 0.8288 0.6696 0.030 Uiso calc R 1 . .
C C13B 0.6182(2) 0.70828(12) 0.61840(12) 0.0492(5) Uani d . 1 . .
H H13D 0.5089 0.7137 0.5879 0.074 Uiso calc R 1 . .
H H13E 0.6311 0.6707 0.6590 0.074 Uiso calc R 1 . .
H H13F 0.6720 0.6813 0.5918 0.074 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
C7A O1A C6A . . 117.08(9) ?
C9A O2A H1OA . . 109.5 ?
C8A N1A N2A . . 105.79(9) ?
C9A N2A N1A . . 111.89(9) ?
C9A N2A C10A . . 127.67(9) ?
N1A N2A C10A . . 120.44(9) ?
C6A C1A C2A . . 119.00(11) ?
C6A C1A H1AA . . 120.5 ?
C2A C1A H1AA . . 120.5 ?
C3A C2A C1A . . 120.90(13) ?
C3A C2A H2AA . . 119.5 ?
C1A C2A H2AA . . 119.5 ?
C4A C3A C2A . . 119.49(12) ?
C4A C3A H3AA . . 120.3 ?
C2A C3A H3AA . . 120.3 ?
C3A C4A C5A . . 120.68(12) ?
C3A C4A H4AA . . 119.7 ?
C5A C4A H4AA . . 119.7 ?
C4A C5A C6A . . 119.18(12) ?
C4A C5A H5AA . . 120.4 ?
C6A C5A H5AA . . 120.4 ?
O1A C6A C1A . . 123.38(10) ?
O1A C6A C5A . . 115.90(10) ?
C1A C6A C5A . . 120.72(11) ?
O1A C7A C9A . . 126.23(10) ?
O1A C7A C8A . . 127.02(10) ?
C9A C7A C8A . . 106.62(9) ?
N1A C8A C7A . . 109.98(10) ?
N1A C8A C12A . . 122.34(10) ?
C7A C8A C12A . . 127.65(10) ?
O2A C9A N2A . . 119.48(10) ?
O2A C9A C7A . . 134.79(10) ?
N2A C9A C7A . . 105.72(9) ?
N2A C10A C11A . . 111.64(10) ?
N2A C10A H10A . . 109.3 ?
C11A C10A H10A . . 109.3 ?
N2A C10A H10B . . 109.3 ?
C11A C10A H10B . . 109.3 ?
H10A C10A H10B . . 108.0 ?
F2A C11A F1A . . 107.48(11) ?
F2A C11A F3A . . 106.96(11) ?
F1A C11A F3A . . 107.17(12) ?
F2A C11A C10A . . 110.45(11) ?
F1A C11A C10A . . 112.14(11) ?
F3A C11A C10A . . 112.37(11) ?
C8A C12A C13A . . 114.89(10) ?
C8A C12A H12A . . 108.5 ?
C13A C12A H12A . . 108.5 ?
C8A C12A H12B . . 108.5 ?
C13A C12A H12B . . 108.5 ?
H12A C12A H12B . . 107.5 ?
C12A C13A H13A . . 109.5 ?
C12A C13A H13B . . 109.5 ?
H13A C13A H13B . . 109.5 ?
C12A C13A H13C . . 109.5 ?
H13A C13A H13C . . 109.5 ?
H13B C13A H13C . . 109.5 ?
C7B O1B C6B . . 119.07(9) ?
C9B O2B H1OB . . 109.5 ?
C8B N1B N2B . . 105.52(9) ?
C9B N2B N1B . . 111.82(9) ?
C9B N2B C10B . . 126.69(9) ?
N1B N2B C10B . . 121.34(9) ?
C6B C1B C2B . . 118.81(11) ?
C6B C1B H1BA . . 120.6 ?
C2B C1B H1BA . . 120.6 ?
C3B C2B C1B . . 120.87(12) ?
C3B C2B H2BA . . 119.6 ?
C1B C2B H2BA . . 119.6 ?
C2B C3B C4B . . 119.64(11) ?
C2B C3B H3BA . . 120.2 ?
C4B C3B H3BA . . 120.2 ?
C3B C4B C5B . . 120.27(11) ?
C3B C4B H4BA . . 119.9 ?
C5B C4B H4BA . . 119.9 ?
C4B C5B C6B . . 119.31(11) ?
C4B C5B H5BA . . 120.3 ?
C6B C5B H5BA . . 120.3 ?
C1B C6B O1B . . 123.89(10) ?
C1B C6B C5B . . 121.09(10) ?
O1B C6B C5B . . 115.02(10) ?
O1B C7B C9B . . 124.29(10) ?
O1B C7B C8B . . 128.23(10) ?
C9B C7B C8B . . 106.69(9) ?
N1B C8B C7B . . 110.12(10) ?
N1B C8B C12B . . 120.60(10) ?
C7B C8B C12B . . 129.26(10) ?
O2B C9B N2B . . 119.65(10) ?
O2B C9B C7B . . 134.49(10) ?
N2B C9B C7B . . 105.84(9) ?
N2B C10B C11B . . 112.69(9) ?
N2B C10B H10C . . 109.1 ?
C11B C10B H10C . . 109.1 ?
N2B C10B H10D . . 109.1 ?
C11B C10B H10D . . 109.1 ?
H10C C10B H10D . . 107.8 ?
F2B C11B F1B . . 107.93(11) ?
F2B C11B F3B . . 107.15(11) ?
F1B C11B F3B . . 107.11(10) ?
F2B C11B C10B . . 112.41(10) ?
F1B C11B C10B . . 109.64(10) ?
F3B C11B C10B . . 112.36(10) ?
C8B C12B C13B . . 113.70(12) ?
C8B C12B H12C . . 108.8 ?
C13B C12B H12C . . 108.8 ?
C8B C12B H12D . . 108.8 ?
C13B C12B H12D . . 108.8 ?
H12C C12B H12D . . 107.7 ?
C12B C13B H13D . . 109.5 ?
C12B C13B H13E . . 109.5 ?
H13D C13B H13E . . 109.5 ?
C12B C13B H13F . . 109.5 ?
H13D C13B H13F . . 109.5 ?
H13E C13B H13F . . 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
F1A C11A . 1.3326(17) ?
F2A C11A . 1.3319(16) ?
F3A C11A . 1.3354(16) ?
O1A C7A . 1.3773(13) ?
O1A C6A . 1.3866(13) ?
O2A C9A . 1.3224(13) ?
O2A H1OA . 0.8200 ?
N1A C8A . 1.3349(14) ?
N1A N2A . 1.3675(13) ?
N2A C9A . 1.3566(13) ?
N2A C10A . 1.4352(14) ?
C1A C6A . 1.3881(16) ?
C1A C2A . 1.3910(17) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.386(2) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.382(2) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.3911(17) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.3929(15) ?
C5A H5AA . 0.9300 ?
C7A C9A . 1.3861(15) ?
C7A C8A . 1.4032(15) ?
C8A C12A . 1.4954(16) ?
C10A C11A . 1.5070(17) ?
C10A H10A . 0.9700 ?
C10A H10B . 0.9700 ?
C12A C13A . 1.5209(18) ?
C12A H12A . 0.9700 ?
C12A H12B . 0.9700 ?
C13A H13A . 0.9600 ?
C13A H13B . 0.9600 ?
C13A H13C . 0.9600 ?
F1B C11B . 1.3354(15) ?
F2B C11B . 1.3351(16) ?
F3B C11B . 1.3367(15) ?
O1B C7B . 1.3822(13) ?
O1B C6B . 1.3871(13) ?
O2B C9B . 1.3162(13) ?
O2B H1OB . 0.8200 ?
N1B C8B . 1.3360(14) ?
N1B N2B . 1.3725(13) ?
N2B C9B . 1.3554(13) ?
N2B C10B . 1.4354(14) ?
C1B C6B . 1.3822(16) ?
C1B C2B . 1.3928(17) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.3848(19) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.387(2) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.3884(17) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.3919(15) ?
C5B H5BA . 0.9300 ?
C7B C9B . 1.3836(15) ?
C7B C8B . 1.4009(15) ?
C8B C12B . 1.4949(17) ?
C10B C11B . 1.5042(16) ?
C10B H10C . 0.9700 ?
C10B H10D . 0.9700 ?
C12B C13B . 1.507(2) ?
C12B H12C . 0.9700 ?
C12B H12D . 0.9700 ?
C13B H13D . 0.9600 ?
C13B H13E . 0.9600 ?
C13B H13F . 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
O2A H1OA N1B 1_455 0.82 1.79 2.5996(15) 169 yes
O2B H1OB N1A 4_676 0.82 1.76 2.5781(14) 177 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
C8A N1A N2A C9A . . . . 0.04(12) ?
C8A N1A N2A C10A . . . . 179.76(10) ?
C6A C1A C2A C3A . . . . 1.65(18) ?
C1A C2A C3A C4A . . . . -0.35(19) ?
C2A C3A C4A C5A . . . . -0.87(19) ?
C3A C4A C5A C6A . . . . 0.75(18) ?
C7A O1A C6A C1A . . . . -0.79(15) ?
C7A O1A C6A C5A . . . . 179.25(10) ?
C2A C1A C6A O1A . . . . 178.28(10) ?
C2A C1A C6A C5A . . . . -1.76(17) ?
C4A C5A C6A O1A . . . . -179.46(10) ?
C4A C5A C6A C1A . . . . 0.58(17) ?
C6A O1A C7A C9A . . . . -103.42(13) ?
C6A O1A C7A C8A . . . . 81.34(14) ?
N2A N1A C8A C7A . . . . -0.27(12) ?
N2A N1A C8A C12A . . . . 177.87(10) ?
O1A C7A C8A N1A . . . . 176.39(10) ?
C9A C7A C8A N1A . . . . 0.39(12) ?
O1A C7A C8A C12A . . . . -1.62(18) ?
C9A C7A C8A C12A . . . . -177.61(11) ?
N1A N2A C9A O2A . . . . -178.67(9) ?
C10A N2A C9A O2A . . . . 1.64(17) ?
N1A N2A C9A C7A . . . . 0.20(12) ?
C10A N2A C9A C7A . . . . -179.49(10) ?
O1A C7A C9A O2A . . . . 2.2(2) ?
C8A C7A C9A O2A . . . . 178.26(12) ?
O1A C7A C9A N2A . . . . -176.39(10) ?
C8A C7A C9A N2A . . . . -0.35(12) ?
C9A N2A C10A C11A . . . . 98.24(13) ?
N1A N2A C10A C11A . . . . -81.44(12) ?
N2A C10A C11A F2A . . . . 177.43(10) ?
N2A C10A C11A F1A . . . . -62.72(14) ?
N2A C10A C11A F3A . . . . 58.09(14) ?
N1A C8A C12A C13A . . . . 40.62(16) y
C7A C8A C12A C13A . . . . -141.59(12) ?
C8B N1B N2B C9B . . . . 0.58(12) ?
C8B N1B N2B C10B . . . . 176.38(10) ?
C6B C1B C2B C3B . . . . -0.03(18) ?
C1B C2B C3B C4B . . . . -0.16(19) ?
C2B C3B C4B C5B . . . . 0.2(2) ?
C3B C4B C5B C6B . . . . -0.10(19) ?
C2B C1B C6B O1B . . . . -179.77(11) ?
C2B C1B C6B C5B . . . . 0.16(17) ?
C7B O1B C6B C1B . . . . -1.95(16) ?
C7B O1B C6B C5B . . . . 178.11(10) ?
C4B C5B C6B C1B . . . . -0.10(17) ?
C4B C5B C6B O1B . . . . 179.84(10) ?
C6B O1B C7B C9B . . . . 109.05(12) ?
C6B O1B C7B C8B . . . . -82.47(14) ?
N2B N1B C8B C7B . . . . -0.54(13) ?
N2B N1B C8B C12B . . . . 178.04(10) ?
O1B C7B C8B N1B . . . . -169.75(10) ?
C9B C7B C8B N1B . . . . 0.33(13) ?
O1B C7B C8B C12B . . . . 11.8(2) ?
C9B C7B C8B C12B . . . . -178.10(12) ?
N1B N2B C9B O2B . . . . 178.28(9) ?
C10B N2B C9B O2B . . . . 2.75(16) ?
N1B N2B C9B C7B . . . . -0.37(12) ?
C10B N2B C9B C7B . . . . -175.90(10) ?
O1B C7B C9B O2B . . . . -7.8(2) ?
C8B C7B C9B O2B . . . . -178.33(12) ?
O1B C7B C9B N2B . . . . 170.60(10) ?
C8B C7B C9B N2B . . . . 0.03(12) ?
C9B N2B C10B C11B . . . . -104.92(13) ?
N1B N2B C10B C11B . . . . 79.95(13) ?
N2B C10B C11B F2B . . . . 63.40(13) ?
N2B C10B C11B F1B . . . . -176.55(10) ?
N2B C10B C11B F3B . . . . -57.56(14) ?
N1B C8B C12B C13B . . . . 111.06(16) y
C7B C8B C12B C13B . . . . -70.65(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079321
