#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/18/2221800.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_2221800
loop_
_publ_author_name
'Shawkataly, Omar bin'
'Pankhi, Mohd. Aslam A.'
'Mohamed-Ibrahim, Mohamed Ismail'
'Hamdan, M. Razak'
'Fun, Hoong-Kun'
_publ_section_title
;
 Tris[3,5-bis(trifluoromethyl)phenyl]phosphine oxide
;
_journal_coeditor_code           SJ2588
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1080
_journal_paper_doi               10.1107/S1600536809013488
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C24 H9 F18 O P'
_chemical_formula_moiety         'C24 H9 F18 O P'
_chemical_formula_sum            'C24 H9 F18 O P'
_chemical_formula_weight         686.28
_chemical_name_systematic
;
Tris[3,5-bis(trifluoromethyl)phenyl]phosphine oxide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.065(10)
_cell_angle_beta                 103.645(10)
_cell_angle_gamma                106.562(10)
_cell_formula_units_Z            2
_cell_length_a                   10.7937(2)
_cell_length_b                   11.8786(10)
_cell_length_c                   12.5066(10)
_cell_measurement_reflns_used    5230
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      1.88
_cell_volume                     1327.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7134
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9473
_exptl_absorpt_correction_T_min  0.8899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.273
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         4535
_refine_ls_number_restraints     168
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.1383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                3611
_reflns_number_total             4535
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2588.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2221800
_cod_database_fobs_code          2221800
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
P P1 0.69584(5) 0.56123(5) 0.16458(4) 0.03853(15) Uani d . 1 . .
O O1 0.66832(14) 0.62576(14) 0.08623(14) 0.0516(4) Uani d . 1 . .
C C1 0.56380(18) 0.52657(18) 0.22911(18) 0.0408(4) Uani d . 1 . .
C C2 0.4957(2) 0.6106(2) 0.24927(19) 0.0473(5) Uani d . 1 . .
H H2A 0.5191 0.6809 0.2305 0.057 Uiso calc R 1 . .
C C3 0.3928(2) 0.5897(2) 0.2974(2) 0.0532(5) Uani d . 1 B .
C C4 0.3564(2) 0.4856(2) 0.3248(2) 0.0552(5) Uani d . 1 . .
H H4A 0.2866 0.4716 0.3562 0.066 Uiso calc R 1 . .
C C5 0.4241(2) 0.4021(2) 0.3053(2) 0.0506(5) Uani d . 1 A .
C C6 0.5283(2) 0.42242(19) 0.25787(19) 0.0460(5) Uani d . 1 . .
H H6A 0.5740 0.3661 0.2455 0.055 Uiso calc R 1 . .
C C7 0.3816(3) 0.2847(3) 0.3293(3) 0.0733(7) Uani d . 1 . .
C C8 0.3197(4) 0.6811(4) 0.3178(3) 0.0804(8) Uani d . 1 . .
C C9 0.70486(19) 0.40435(18) 0.08552(17) 0.0404(4) Uani d . 1 . .
C C10 0.5806(2) 0.29374(19) 0.00606(18) 0.0459(5) Uani d . 1 . .
H H10A 0.4954 0.3003 -0.0021 0.055 Uiso calc R 1 . .
C C11 0.5843(2) 0.1740(2) -0.0606(2) 0.0531(5) Uani d . 1 D .
C C12 0.7100(2) 0.1634(2) -0.0525(2) 0.0574(6) Uani d . 1 . .
H H12A 0.7117 0.0828 -0.0982 0.069 Uiso calc R 1 . .
C C13 0.8329(2) 0.2734(2) 0.02403(19) 0.0537(5) Uani d . 1 C .
C C14 0.8311(2) 0.3936(2) 0.09427(18) 0.0474(5) Uani d . 1 . .
H H14A 0.9146 0.4669 0.1472 0.057 Uiso calc R 1 . .
C C15 0.4488(3) 0.0560(3) -0.1458(3) 0.0801(8) Uani d . 1 . .
C C16 0.9705(3) 0.2659(3) 0.0296(3) 0.0809(9) Uani d . 1 . .
C C17 0.85895(18) 0.66656(17) 0.29756(17) 0.0378(4) Uani d . 1 . .
C C18 0.94351(19) 0.78052(18) 0.29999(18) 0.0422(4) Uani d . 1 . .
H H18A 0.9176 0.7986 0.2337 0.051 Uiso calc R 1 . .
C C19 1.0671(2) 0.86781(18) 0.40158(19) 0.0445(5) Uani d . 1 E .
C C20 1.1054(2) 0.84267(19) 0.50081(19) 0.0475(5) Uani d . 1 . .
H H20A 1.1879 0.9015 0.5688 0.057 Uiso calc R 1 . .
C C21 1.0203(2) 0.72894(19) 0.49895(18) 0.0436(4) Uani d . 1 F .
C C22 0.89764(19) 0.64089(18) 0.39795(18) 0.0417(4) Uani d . 1 . .
H H22A 0.8411 0.5647 0.3970 0.050 Uiso calc R 1 . .
C C23 1.1590(3) 0.9907(2) 0.4026(2) 0.0608(6) Uani d . 1 . .
C C24 1.0639(3) 0.7057(2) 0.6091(2) 0.0627(6) Uani d . 1 . .
F F1A 0.3107(17) 0.2938(11) 0.4026(13) 0.127(3) Uani d PU 0.64(3) A 1
F F2A 0.3053(13) 0.1725(6) 0.2330(7) 0.106(2) Uani d PU 0.64(3) A 1
F F3A 0.4911(12) 0.2685(12) 0.3845(8) 0.103(3) Uani d PU 0.64(3) A 1
F F1B 0.347(2) 0.3116(17) 0.4269(11) 0.101(4) Uani d PU 0.36(3) A 2
F F2B 0.265(3) 0.1929(19) 0.2265(17) 0.167(8) Uani d PU 0.36(3) A 2
F F3B 0.474(3) 0.238(3) 0.345(4) 0.143(8) Uani d PU 0.36(3) A 2
F F4A 0.2145(11) 0.6369(9) 0.3520(13) 0.132(3) Uani d PU 0.649(14) B 1
F F5A 0.4017(7) 0.7979(6) 0.3979(11) 0.149(4) Uani d PU 0.649(14) B 1
F F6A 0.2564(13) 0.6778(13) 0.2152(7) 0.149(4) Uani d PU 0.649(14) B 1
F F4B 0.3833(18) 0.7925(14) 0.307(2) 0.129(5) Uani d PU 0.351(14) B 2
F F5B 0.2026(13) 0.6458(12) 0.242(2) 0.153(9) Uani d PU 0.351(14) B 2
F F6B 0.319(2) 0.733(2) 0.4278(10) 0.134(7) Uani d PU 0.351(14) B 2
F F7A 1.0083(16) 0.289(3) -0.0448(13) 0.171(6) Uani d PU 0.52(2) C 1
F F8A 0.9558(9) 0.1390(8) 0.010(2) 0.166(6) Uani d PU 0.52(2) C 1
F F9A 1.0656(11) 0.3334(14) 0.1386(10) 0.123(5) Uani d PU 0.52(2) C 1
F F7B 1.0531(13) 0.3664(12) 0.009(2) 0.142(5) Uani d PU 0.48(2) C 2
F F8B 0.9664(8) 0.1631(12) -0.0554(10) 0.112(4) Uani d PU 0.48(2) C 2
F F9B 1.0478(16) 0.292(2) 0.1352(11) 0.141(6) Uani d PU 0.48(2) C 2
F F10A 0.3748(10) 0.0774(10) -0.2275(11) 0.124(4) Uani d PU 0.545(16) D 1
F F11A 0.3666(10) 0.0405(10) -0.0809(7) 0.124(3) Uani d PU 0.545(16) D 1
F F12A 0.4594(10) -0.0513(8) -0.1913(19) 0.174(6) Uani d PU 0.545(16) D 1
F F10B 0.4473(14) -0.0498(9) -0.1405(11) 0.125(5) Uani d PU 0.455(16) D 2
F F11B 0.4366(18) 0.0163(16) -0.2650(6) 0.151(6) Uani d PU 0.455(16) D 2
F F12B 0.3425(7) 0.0689(11) -0.140(3) 0.215(10) Uani d PU 0.455(16) D 2
F F13A 1.2266(7) 1.0906(3) 0.5147(3) 0.107(2) Uani d PU 0.774(9) E 1
F F14A 1.0835(3) 1.0359(4) 0.3402(5) 0.0925(13) Uani d PU 0.774(9) E 1
F F15A 1.2459(5) 0.9734(4) 0.3515(6) 0.102(2) Uani d PU 0.774(9) E 1
F F13B 1.2974(10) 1.030(2) 0.481(2) 0.119(7) Uani d PU 0.226(9) E 2
F F14B 1.136(3) 1.0800(13) 0.438(4) 0.163(11) Uani d PU 0.226(9) E 2
F F15B 1.184(3) 0.9613(17) 0.3041(18) 0.156(11) Uani d PU 0.226(9) E 2
F F16A 1.1855(12) 0.6770(8) 0.6200(8) 0.082(2) Uani d PU 0.63(5) F 2
F F17A 1.1071(13) 0.8101(11) 0.7152(10) 0.094(3) Uani d PU 0.63(5) F 2
F F18A 0.9620(17) 0.6078(13) 0.6047(10) 0.092(3) Uani d PU 0.63(5) F 2
F F16B 1.162(2) 0.689(2) 0.625(2) 0.132(7) Uani d PU 0.37(5) F 1
F F17B 1.068(5) 0.802(2) 0.7088(18) 0.117(6) Uani d PU 0.37(5) F 1
F F18B 0.978(2) 0.5964(15) 0.6035(17) 0.073(4) Uani d PU 0.37(5) F 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'
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'
P P 0.1023 0.0942 '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
O1 P1 C9 . . 114.30(9) ?
O1 P1 C17 . . 111.18(8) ?
C9 P1 C17 . . 107.20(8) ?
O1 P1 C1 . . 113.04(8) ?
C9 P1 C1 . . 105.36(9) ?
C17 P1 C1 . . 105.12(8) ?
C6 C1 C2 . . 119.39(18) ?
C6 C1 P1 . . 123.91(14) ?
C2 C1 P1 . . 116.70(15) ?
C3 C2 C1 . . 120.0(2) ?
C3 C2 H2A . . 120.0 ?
C1 C2 H2A . . 120.0 ?
C4 C3 C2 . . 120.7(2) ?
C4 C3 C8 . . 120.1(2) ?
C2 C3 C8 . . 119.2(2) ?
C3 C4 C5 . . 119.53(19) ?
C3 C4 H4A . . 120.2 ?
C5 C4 H4A . . 120.2 ?
C4 C5 C6 . . 120.4(2) ?
C4 C5 C7 . . 120.3(2) ?
C6 C5 C7 . . 119.3(2) ?
C1 C6 C5 . . 120.01(18) ?
C1 C6 H6A . . 120.0 ?
C5 C6 H6A . . 120.0 ?
F3B C7 F2A . . 86.2(14) ?
F3B C7 F1B . . 108.0(14) ?
F2A C7 F1B . . 118.1(8) ?
F3B C7 F1A . . 118.5(11) ?
F2A C7 F1A . . 104.9(7) ?
F2A C7 F3A . . 104.5(7) ?
F1B C7 F3A . . 92.2(9) ?
F1A C7 F3A . . 105.4(8) ?
F3B C7 F2B . . 110.3(12) ?
F1B C7 F2B . . 108.4(11) ?
F1A C7 F2B . . 92.6(10) ?
F3A C7 F2B . . 128.3(13) ?
F3B C7 C5 . . 114.7(9) ?
F2A C7 C5 . . 115.9(5) ?
F1B C7 C5 . . 111.4(7) ?
F1A C7 C5 . . 113.4(4) ?
F3A C7 C5 . . 111.8(6) ?
F2B C7 C5 . . 103.9(8) ?
F5B C8 F5A . . 126.4(6) ?
F5A C8 F6A . . 110.9(6) ?
F5B C8 F6B . . 108.5(8) ?
F5A C8 F6B . . 57.5(8) ?
F6A C8 F6B . . 133.5(5) ?
F5B C8 F4A . . 65.5(10) ?
F5A C8 F4A . . 109.6(5) ?
F6A C8 F4A . . 102.7(5) ?
F6B C8 F4A . . 54.4(8) ?
F5B C8 F4B . . 96.6(8) ?
F5A C8 F4B . . 48.0(6) ?
F6A C8 F4B . . 66.4(7) ?
F6B C8 F4B . . 101.1(9) ?
F4A C8 F4B . . 136.2(4) ?
F5B C8 C3 . . 119.3(6) ?
F5A C8 C3 . . 112.2(3) ?
F6A C8 C3 . . 110.6(4) ?
F6B C8 C3 . . 115.2(4) ?
F4A C8 C3 . . 110.3(3) ?
F4B C8 C3 . . 113.1(4) ?
C14 C9 C10 . . 119.36(18) ?
C14 C9 P1 . . 122.02(14) ?
C10 C9 P1 . . 118.42(14) ?
C11 C10 C9 . . 119.79(18) ?
C11 C10 H10A . . 120.1 ?
C9 C10 H10A . . 120.1 ?
C12 C11 C10 . . 120.84(18) ?
C12 C11 C15 . . 120.3(2) ?
C10 C11 C15 . . 118.9(2) ?
C13 C12 C11 . . 119.3(2) ?
C13 C12 H12A . . 120.3 ?
C11 C12 H12A . . 120.3 ?
C12 C13 C14 . . 120.58(19) ?
C12 C13 C16 . . 120.3(2) ?
C14 C13 C16 . . 119.1(2) ?
C9 C14 C13 . . 120.04(18) ?
C9 C14 H14A . . 120.0 ?
C13 C14 H14A . . 120.0 ?
F12B C15 F12A . . 125.6(6) ?
F12B C15 F10B . . 110.1(12) ?
F12B C15 F10A . . 59.9(12) ?
F12A C15 F10A . . 113.0(7) ?
F10B C15 F10A . . 132.8(6) ?
F12B C15 F11B . . 107.1(10) ?
F12A C15 F11B . . 67.5(6) ?
F10B C15 F11B . . 97.3(8) ?
F10A C15 F11B . . 52.6(6) ?
F12A C15 F11A . . 105.5(8) ?
F10B C15 F11A . . 77.7(7) ?
F10A C15 F11A . . 101.5(6) ?
F11B C15 F11A . . 139.0(6) ?
F12B C15 C11 . . 116.7(4) ?
F12A C15 C11 . . 115.2(5) ?
F10B C15 C11 . . 113.1(6) ?
F10A C15 C11 . . 111.6(4) ?
F11B C15 C11 . . 110.5(4) ?
F11A C15 C11 . . 108.7(4) ?
F7A C16 F9B . . 126.0(9) ?
F7A C16 F8B . . 67.9(8) ?
F9B C16 F8B . . 112.0(8) ?
F7A C16 F9A . . 112.2(10) ?
F8B C16 F9A . . 124.6(7) ?
F7A C16 F8A . . 109.7(7) ?
F9B C16 F8A . . 80.4(9) ?
F9A C16 F8A . . 100.0(9) ?
F9B C16 F7B . . 101.4(8) ?
F8B C16 F7B . . 100.6(6) ?
F9A C16 F7B . . 82.5(9) ?
F8A C16 F7B . . 136.6(8) ?
F7A C16 C13 . . 112.9(6) ?
F9B C16 C13 . . 113.6(7) ?
F8B C16 C13 . . 116.5(4) ?
F9A C16 C13 . . 113.4(6) ?
F8A C16 C13 . . 107.7(6) ?
F7B C16 C13 . . 110.8(5) ?
C18 C17 C22 . . 119.66(17) ?
C18 C17 P1 . . 117.27(15) ?
C22 C17 P1 . . 122.98(14) ?
C17 C18 C19 . . 119.98(19) ?
C17 C18 H18A . . 120.0 ?
C19 C18 H18A . . 120.0 ?
C20 C19 C18 . . 120.43(18) ?
C20 C19 C23 . . 120.03(18) ?
C18 C19 C23 . . 119.5(2) ?
C19 C20 C21 . . 119.68(18) ?
C19 C20 H20A . . 120.2 ?
C21 C20 H20A . . 120.2 ?
C22 C21 C20 . . 120.38(19) ?
C22 C21 C24 . . 121.32(18) ?
C20 C21 C24 . . 118.29(18) ?
C21 C22 C17 . . 119.86(17) ?
C21 C22 H22A . . 120.1 ?
C17 C22 H22A . . 120.1 ?
F14B C23 F15B . . 117.7(15) ?
F14B C23 F15A . . 128.5(7) ?
F14B C23 F13A . . 55(2) ?
F15B C23 F13A . . 133.0(8) ?
F15A C23 F13A . . 109.2(3) ?
F14B C23 F14A . . 50(2) ?
F15B C23 F14A . . 76.9(14) ?
F15A C23 F14A . . 105.2(3) ?
F13A C23 F14A . . 103.7(3) ?
F14B C23 F13B . . 104.7(14) ?
F15B C23 F13B . . 95.3(11) ?
F15A C23 F13B . . 62.9(10) ?
F13A C23 F13B . . 53.5(10) ?
F14A C23 F13B . . 139.5(5) ?
F14B C23 C19 . . 117.4(6) ?
F15B C23 C19 . . 110.3(7) ?
F15A C23 C19 . . 113.7(3) ?
F13A C23 C19 . . 112.7(2) ?
F14A C23 C19 . . 111.5(2) ?
F13B C23 C19 . . 108.5(5) ?
F16B C24 F17A . . 97.2(13) ?
F16B C24 F18A . . 110.4(12) ?
F17A C24 F18A . . 108.7(7) ?
F16B C24 F18B . . 99.9(13) ?
F17A C24 F18B . . 113.2(9) ?
F16B C24 F17B . . 112.9(19) ?
F18A C24 F17B . . 96.7(14) ?
F18B C24 F17B . . 103.4(16) ?
F17A C24 F16A . . 101.4(7) ?
F18A C24 F16A . . 109.1(9) ?
F18B C24 F16A . . 98.5(9) ?
F17B C24 F16A . . 117(2) ?
F16B C24 C21 . . 114.0(12) ?
F17A C24 C21 . . 114.0(7) ?
F18A C24 C21 . . 111.6(6) ?
F18B C24 C21 . . 116.0(8) ?
F17B C24 C21 . . 109.9(12) ?
F16A C24 C21 . . 111.6(4) ?
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
P1 O1 . 1.4726(15) ?
P1 C9 . 1.8122(19) ?
P1 C17 . 1.8160(19) ?
P1 C1 . 1.8163(19) ?
C1 C6 . 1.386(3) ?
C1 C2 . 1.387(3) ?
C2 C3 . 1.386(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.376(3) ?
C3 C8 . 1.500(3) ?
C4 C5 . 1.379(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.392(3) ?
C5 C7 . 1.498(3) ?
C6 H6A . 0.9300 ?
C7 F3B . 1.286(19) ?
C7 F2A . 1.287(7) ?
C7 F1B . 1.320(13) ?
C7 F1A . 1.321(8) ?
C7 F3A . 1.323(11) ?
C7 F2B . 1.368(15) ?
C8 F5B . 1.232(10) ?
C8 F5A . 1.263(6) ?
C8 F6A . 1.285(7) ?
C8 F6B . 1.293(8) ?
C8 F4A . 1.341(5) ?
C8 F4B . 1.374(10) ?
C9 C14 . 1.387(3) ?
C9 C10 . 1.393(3) ?
C10 C11 . 1.384(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.382(3) ?
C11 C15 . 1.504(3) ?
C12 C13 . 1.377(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.390(3) ?
C13 C16 . 1.500(3) ?
C14 H14A . 0.9300 ?
C15 F12B . 1.215(9) ?
C15 F12A . 1.246(7) ?
C15 F10B . 1.277(9) ?
C15 F10A . 1.290(7) ?
C15 F11B . 1.352(10) ?
C15 F11A . 1.354(8) ?
C16 F7A . 1.187(11) ?
C16 F9B . 1.256(11) ?
C16 F8B . 1.279(7) ?
C16 F9A . 1.280(10) ?
C16 F8A . 1.392(11) ?
C16 F7B . 1.417(9) ?
C17 C18 . 1.385(3) ?
C17 C22 . 1.394(3) ?
C18 C19 . 1.391(3) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.377(3) ?
C19 C23 . 1.506(3) ?
C20 C21 . 1.389(3) ?
C20 H20A . 0.9300 ?
C21 C22 . 1.383(3) ?
C21 C24 . 1.496(3) ?
C22 H22A . 0.9300 ?
C23 F14B . 1.117(9) ?
C23 F15B . 1.268(16) ?
C23 F15A . 1.277(4) ?
C23 F13A . 1.317(4) ?
C23 F14A . 1.346(4) ?
C23 F13B . 1.412(10) ?
C24 F16B . 1.11(3) ?
C24 F17A . 1.308(11) ?
C24 F18A . 1.327(11) ?
C24 F18B . 1.330(17) ?
C24 F17B . 1.33(2) ?
C24 F16A . 1.436(15) ?
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
C18 H18A O1 . 0.93 2.58 2.992(3) 108 y
C10 H10A O1 2_665 0.93 2.38 3.203(3) 147 y
C20 H20A F10A 1_666 0.93 2.50 3.418(12) 167 y
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
O1 P1 C1 C6 . . . . 150.78(16) ?
C9 P1 C1 C6 . . . . 25.28(19) ?
C17 P1 C1 C6 . . . . -87.79(17) ?
O1 P1 C1 C2 . . . . -28.91(18) ?
C9 P1 C1 C2 . . . . -154.40(15) ?
C17 P1 C1 C2 . . . . 92.53(16) ?
C6 C1 C2 C3 . . . . -0.2(3) ?
P1 C1 C2 C3 . . . . 179.48(16) ?
C1 C2 C3 C4 . . . . -0.5(3) ?
C1 C2 C3 C8 . . . . -179.6(2) ?
C2 C3 C4 C5 . . . . 0.7(3) ?
C8 C3 C4 C5 . . . . 179.8(2) ?
C3 C4 C5 C6 . . . . -0.3(3) ?
C3 C4 C5 C7 . . . . -177.3(2) ?
C2 C1 C6 C5 . . . . 0.7(3) ?
P1 C1 C6 C5 . . . . -179.01(15) ?
C4 C5 C6 C1 . . . . -0.4(3) ?
C7 C5 C6 C1 . . . . 176.6(2) ?
C4 C5 C7 F3B . . . . -160(2) ?
C6 C5 C7 F3B . . . . 23(2) ?
C4 C5 C7 F2A . . . . 101.8(7) ?
C6 C5 C7 F2A . . . . -75.3(7) ?
C4 C5 C7 F1B . . . . -37.0(9) ?
C6 C5 C7 F1B . . . . 145.9(9) ?
C4 C5 C7 F1A . . . . -19.6(9) ?
C6 C5 C7 F1A . . . . 163.3(9) ?
C4 C5 C7 F3A . . . . -138.6(5) ?
C6 C5 C7 F3A . . . . 44.3(6) ?
C4 C5 C7 F2B . . . . 79.5(15) ?
C6 C5 C7 F2B . . . . -97.6(15) ?
C4 C3 C8 F5B . . . . -78.3(16) ?
C2 C3 C8 F5B . . . . 100.9(16) ?
C4 C3 C8 F5A . . . . 116.9(9) ?
C2 C3 C8 F5A . . . . -64.0(9) ?
C4 C3 C8 F6A . . . . -118.7(8) ?
C2 C3 C8 F6A . . . . 60.5(8) ?
C4 C3 C8 F6B . . . . 53.5(15) ?
C2 C3 C8 F6B . . . . -127.4(15) ?
C4 C3 C8 F4A . . . . -5.7(8) ?
C2 C3 C8 F4A . . . . 173.4(7) ?
C4 C3 C8 F4B . . . . 169.1(12) ?
C2 C3 C8 F4B . . . . -11.7(13) ?
O1 P1 C9 C14 . . . . 98.19(17) ?
C17 P1 C9 C14 . . . . -25.50(19) ?
C1 P1 C9 C14 . . . . -137.10(17) ?
O1 P1 C9 C10 . . . . -76.64(17) ?
C17 P1 C9 C10 . . . . 159.67(16) ?
C1 P1 C9 C10 . . . . 48.06(18) ?
C14 C9 C10 C11 . . . . 1.7(3) ?
P1 C9 C10 C11 . . . . 176.64(16) ?
C9 C10 C11 C12 . . . . -2.1(3) ?
C9 C10 C11 C15 . . . . -180.0(2) ?
C10 C11 C12 C13 . . . . 0.7(4) ?
C15 C11 C12 C13 . . . . 178.5(2) ?
C11 C12 C13 C14 . . . . 1.1(4) ?
C11 C12 C13 C16 . . . . -177.0(3) ?
C10 C9 C14 C13 . . . . 0.1(3) ?
P1 C9 C14 C13 . . . . -174.68(17) ?
C12 C13 C14 C9 . . . . -1.5(3) ?
C16 C13 C14 C9 . . . . 176.6(2) ?
C12 C11 C15 F12B . . . . 173(2) ?
C10 C11 C15 F12B . . . . -9(2) ?
C12 C11 C15 F12A . . . . 10.3(14) ?
C10 C11 C15 F12A . . . . -171.8(13) ?
C12 C11 C15 F10B . . . . 44.2(9) ?
C10 C11 C15 F10B . . . . -137.9(8) ?
C12 C11 C15 F10A . . . . -120.4(10) ?
C10 C11 C15 F10A . . . . 57.5(10) ?
C12 C11 C15 F11B . . . . -63.8(13) ?
C10 C11 C15 F11B . . . . 114.2(13) ?
C12 C11 C15 F11A . . . . 128.4(6) ?
C10 C11 C15 F11A . . . . -53.6(7) ?
C12 C13 C16 F7A . . . . 88.9(15) ?
C14 C13 C16 F7A . . . . -89.2(15) ?
C12 C13 C16 F9B . . . . -119.3(12) ?
C14 C13 C16 F9B . . . . 62.5(12) ?
C12 C13 C16 F8B . . . . 13.2(11) ?
C14 C13 C16 F8B . . . . -165.0(10) ?
C12 C13 C16 F9A . . . . -142.0(9) ?
C14 C13 C16 F9A . . . . 39.9(9) ?
C12 C13 C16 F8A . . . . -32.3(13) ?
C14 C13 C16 F8A . . . . 149.6(13) ?
C12 C13 C16 F7B . . . . 127.3(10) ?
C14 C13 C16 F7B . . . . -50.9(10) ?
O1 P1 C17 C18 . . . . -8.74(17) ?
C9 P1 C17 C18 . . . . 116.84(15) ?
C1 P1 C17 C18 . . . . -131.39(14) ?
O1 P1 C17 C22 . . . . 167.85(15) ?
C9 P1 C17 C22 . . . . -66.56(17) ?
C1 P1 C17 C22 . . . . 45.21(17) ?
C22 C17 C18 C19 . . . . 0.8(3) ?
P1 C17 C18 C19 . . . . 177.48(14) ?
C17 C18 C19 C20 . . . . -0.8(3) ?
C17 C18 C19 C23 . . . . 179.34(18) ?
C18 C19 C20 C21 . . . . 0.3(3) ?
C23 C19 C20 C21 . . . . -179.81(19) ?
C19 C20 C21 C22 . . . . 0.2(3) ?
C19 C20 C21 C24 . . . . -179.0(2) ?
C20 C21 C22 C17 . . . . -0.2(3) ?
C24 C21 C22 C17 . . . . 178.99(19) ?
C18 C17 C22 C21 . . . . -0.3(3) ?
P1 C17 C22 C21 . . . . -176.79(14) ?
C20 C19 C23 F14B . . . . -93(3) ?
C18 C19 C23 F14B . . . . 87(3) ?
C20 C19 C23 F15B . . . . 128.5(17) ?
C18 C19 C23 F15B . . . . -51.6(17) ?
C20 C19 C23 F15A . . . . 93.1(4) ?
C18 C19 C23 F15A . . . . -87.0(4) ?
C20 C19 C23 F13A . . . . -31.9(5) ?
C18 C19 C23 F13A . . . . 148.0(4) ?
C20 C19 C23 F14A . . . . -148.1(3) ?
C18 C19 C23 F14A . . . . 31.8(4) ?
C20 C19 C23 F13B . . . . 25.4(14) ?
C18 C19 C23 F13B . . . . -154.8(14) ?
C22 C21 C24 F16B . . . . 115.3(11) ?
C20 C21 C24 F16B . . . . -65.5(12) ?
C22 C21 C24 F17A . . . . -134.3(7) ?
C20 C21 C24 F17A . . . . 44.9(7) ?
C22 C21 C24 F18A . . . . -10.7(9) ?
C20 C21 C24 F18A . . . . 168.5(8) ?
C22 C21 C24 F18B . . . . 0.0(9) ?
C20 C21 C24 F18B . . . . 179.2(9) ?
C22 C21 C24 F17B . . . . -117(2) ?
C20 C21 C24 F17B . . . . 62(2) ?
C22 C21 C24 F16A . . . . 111.6(3) ?
C20 C21 C24 F16A . . . . -69.2(4) ?
