#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:54:10 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257700 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/87/1558787.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_1558787
loop_
_publ_author_name
'Reichel, Marco'
'Unger, Cornelia'
'Dubovnik, Sviatlana'
'Roidl, Andreas'
'Kornath, Andreas'
'Karaghiosoff, Konstantin'
_publ_section_title
;
 Synthesis, structural and toxicological investigations of quarternary
 phosphonium salts containing the P-bonded bioisosteric CH2F moiety
;
_journal_issue                   33
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14306
_journal_page_last               14315
_journal_paper_doi               10.1039/D0NJ02310H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C37 H30 F O P2, I, 0.284(H2 O)'
_chemical_formula_sum            'C37 H30.57 F I O1.28 P2'
_chemical_formula_weight         703.57
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-04-04 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                64.227(4)
_cell_angle_beta                 66.641(3)
_cell_angle_gamma                68.195(4)
_cell_formula_units_Z            2
_cell_length_a                   11.3894(4)
_cell_length_b                   13.0313(6)
_cell_length_c                   13.4302(4)
_cell_measurement_reflns_used    9356
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.0750
_cell_measurement_theta_min      4.4330
_cell_volume                     1599.41(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32102
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         4.110
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             710
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         2.846
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         9734
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²+1.4210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7866
_reflns_number_total             9734
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj02310h2.cif
_cod_data_source_block           test1_CCDC4
_cod_depositor_comments
;Adding full bibliography for 1558783--1558787.cif.

 Adding full bibliography for 1558783--1558787.cif.
;
_cod_original_cell_volume        1599.41(13)
_cod_database_code               1558787
_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.
;
_shelx_estimated_absorpt_t_min   0.764
_shelx_estimated_absorpt_t_max   0.915
_shelxl_version_number           2014-3
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
I1 I 0.28798(2) 0.12770(2) 0.75565(2) 0.03563(6) Uani 1 1 d . . . . .
P2 P 0.17338(6) 0.46822(5) 0.16748(5) 0.02383(12) Uani 1 1 d . . . . .
P1 P -0.00241(6) 0.22381(5) 0.55371(5) 0.02181(12) Uani 1 1 d . . . . .
O1 O 0.22289(16) 0.27838(14) 0.36446(15) 0.0280(4) Uani 1 1 d . . . . .
C14 C 0.1482(2) 0.11954(19) 0.51993(18) 0.0208(4) Uani 1 1 d . . . . .
C11 C -0.1911(3) 0.4119(3) 0.2589(3) 0.0451(7) Uani 1 1 d . . . . .
H11 H -0.2332(16) 0.4542(16) 0.193(2) 0.054 Uiso 1 1 calc R U . . .
C22 C 0.4499(3) 0.4127(2) 0.3733(2) 0.0324(5) Uani 1 1 d . . . . .
H22 H 0.5026(18) 0.4009(5) 0.4181(16) 0.039 Uiso 1 1 calc R U . . .
C2 C -0.1135(2) 0.1515(2) 0.6810(2) 0.0254(4) Uani 1 1 d . . . . .
C15 C 0.1655(2) -0.0001(2) 0.5834(2) 0.0250(4) Uani 1 1 d . . . . .
H15 H 0.095(2) -0.0289(9) 0.646(2) 0.030 Uiso 1 1 calc R U . . .
C13 C -0.0363(3) 0.2503(2) 0.3504(2) 0.0299(5) Uani 1 1 d . . . . .
H13 H 0.028(2) 0.182(2) 0.3514(2) 0.036 Uiso 1 1 calc R U . . .
C19 C 0.2527(2) 0.1602(2) 0.42808(19) 0.0230(4) Uani 1 1 d . . . . .
C25 C 0.2931(2) 0.45011(19) 0.23794(19) 0.0221(4) Uani 1 1 d . . . . .
C16 C 0.2861(3) -0.0769(2) 0.5546(2) 0.0285(5) Uani 1 1 d . . . . .
H16 H 0.2975(5) -0.151(3) 0.5937(15) 0.034 Uiso 1 1 calc R U . . .
C1 C 0.0365(3) 0.3308(2) 0.5824(2) 0.0305(5) Uani 1 1 d . . . . .
H1A H 0.0890(13) 0.2914(9) 0.6338(12) 0.037 Uiso 1 1 calc R U . . .
H1B H 0.0844(12) 0.3780(11) 0.5132(16) 0.037 Uiso 1 1 calc R U . . .
F1 F -0.07871(17) 0.40001(15) 0.62946(16) 0.0438(4) Uani 1 1 d . . . . .
C20 C 0.3039(2) 0.3509(2) 0.33571(19) 0.0233(4) Uani 1 1 d . . . . .
C17 C 0.3877(2) -0.0344(2) 0.4630(2) 0.0299(5) Uani 1 1 d . . . . .
H17 H 0.4696 -0.0876 0.4436 0.036 Uiso 1 1 calc R U . . .
C12 C -0.0962(3) 0.3085(3) 0.2612(2) 0.0378(6) Uani 1 1 d . . . . .
H12 H -0.0729(10) 0.2785(13) 0.205(2) 0.045 Uiso 1 1 calc R U . . .
C32 C 0.1813(2) 0.6105(2) 0.0530(2) 0.0260(5) Uani 1 1 d . . . . .
C23 C 0.4426(3) 0.5123(2) 0.2755(2) 0.0323(5) Uani 1 1 d . . . . .
H23 H 0.4904(17) 0.567(2) 0.2544(8) 0.039 Uiso 1 1 calc R U . . .
C24 C 0.3645(2) 0.5305(2) 0.2093(2) 0.0272(5) Uani 1 1 d . . . . .
H24 H 0.3597(3) 0.597(2) 0.145(2) 0.033 Uiso 1 1 calc R U . . .
C26 C 0.2672(2) 0.3690(2) 0.08427(19) 0.0242(4) Uani 1 1 d . . . . .
C18 C 0.3726(2) 0.0837(2) 0.3992(2) 0.0290(5) Uani 1 1 d . . . . .
H18 H 0.436(2) 0.1089(10) 0.343(2) 0.035 Uiso 1 1 calc R U . . .
C37 C 0.2869(3) 0.6317(2) -0.0448(2) 0.0328(5) Uani 1 1 d . . . . .
H37 H 0.361(3) 0.570(2) -0.0557(5) 0.039 Uiso 1 1 calc R U . . .
C3 C -0.1035(3) 0.1294(2) 0.7892(2) 0.0318(5) Uani 1 1 d . . . . .
H3 H -0.039(2) 0.1546(9) 0.7957(3) 0.038 Uiso 1 1 calc R U . . .
C31 C 0.2032(3) 0.3591(2) 0.0208(2) 0.0317(5) Uani 1 1 d . . . . .
H31 H 0.116(3) 0.3993(15) 0.0249(3) 0.038 Uiso 1 1 calc R U . . .
C28 C 0.4612(3) 0.2332(3) 0.0123(2) 0.0364(6) Uani 1 1 d . . . . .
H28 H 0.550(3) 0.1886(16) 0.0106(3) 0.044 Uiso 1 1 calc R U . . .
C7 C -0.2067(3) 0.1138(3) 0.6715(3) 0.0425(7) Uani 1 1 d . . . . .
H7 H -0.2135(4) 0.1292(7) 0.601(3) 0.051 Uiso 1 1 calc R U . . .
C8 C -0.0759(2) 0.2965(2) 0.4374(2) 0.0268(5) Uani 1 1 d . . . . .
C30 C 0.2690(3) 0.2893(2) -0.0488(2) 0.0371(6) Uani 1 1 d . . . . .
H30 H 0.2283(17) 0.2849(3) -0.0901(17) 0.045 Uiso 1 1 calc R U . . .
C27 C 0.3965(2) 0.3040(2) 0.0804(2) 0.0308(5) Uani 1 1 d . . . . .
H27 H 0.4383(15) 0.3079(3) 0.1224(15) 0.037 Uiso 1 1 calc R U . . .
C21 C 0.3797(2) 0.3311(2) 0.4048(2) 0.0278(5) Uani 1 1 d . . . . .
H21 H 0.3832(3) 0.266(2) 0.470(2) 0.033 Uiso 1 1 calc R U . . .
C29 C 0.3979(3) 0.2269(2) -0.0532(2) 0.0347(6) Uani 1 1 d . . . . .
H29 H 0.4431(17) 0.1797(17) -0.1012(18) 0.042 Uiso 1 1 calc R U . . .
C33 C 0.0698(3) 0.7026(2) 0.0663(2) 0.0361(6) Uani 1 1 d . . . . .
H33 H -0.011(3) 0.6873(6) 0.139(2) 0.043 Uiso 1 1 calc R U . . .
C4 C -0.1888(3) 0.0700(2) 0.8873(2) 0.0349(6) Uani 1 1 d . . . . .
H4 H -0.1851(3) 0.0575(6) 0.956(3) 0.042 Uiso 1 1 calc R U . . .
C9 C -0.1732(3) 0.4009(3) 0.4356(3) 0.0399(6) Uani 1 1 d . . . . .
H9 H -0.2003(11) 0.4318(12) 0.495(2) 0.048 Uiso 1 1 calc R U . . .
C36 C 0.2828(3) 0.7438(3) -0.1270(3) 0.0435(7) Uani 1 1 d . . . . .
H36 H 0.3557 0.7578 -0.1934 0.052 Uiso 1 1 calc R U . . .
C34 C 0.0658(4) 0.8134(3) -0.0155(3) 0.0480(8) Uani 1 1 d . . . . .
H34 H -0.014(3) 0.878(3) -0.0055(5) 0.058 Uiso 1 1 calc R U . . .
C35 C 0.1734(4) 0.8344(3) -0.1121(3) 0.0495(9) Uani 1 1 d . . . . .
H35 H 0.1714(4) 0.909(3) -0.167(2) 0.059 Uiso 1 1 calc R U . . .
C5 C -0.2789(3) 0.0308(3) 0.8773(3) 0.0408(7) Uani 1 1 d . . . . .
H5 H -0.333(2) -0.0107(17) 0.943(3) 0.049 Uiso 1 1 calc R U . . .
C10 C -0.2294(3) 0.4586(3) 0.3446(3) 0.0497(8) Uani 1 1 d . . . . .
H10 H -0.292(3) 0.528(3) 0.3416(3) 0.060 Uiso 1 1 calc R U . . .
C6 C -0.2892(4) 0.0526(3) 0.7703(3) 0.0527(9) Uani 1 1 d . . . . .
H6 H -0.352(3) 0.0262(12) 0.7645(4) 0.063 Uiso 1 1 calc R U . . .
O2 O 0.5096(10) 0.3023(9) 0.6254(9) 0.062(4) Uani 0.284(9) 1 d D . P . .
H210 H 0.575(9) 0.244(7) 0.650(13) 0.074 Uiso 0.284(9) 1 d D U P . .
H211 H 0.459(11) 0.265(9) 0.626(13) 0.074 Uiso 0.284(9) 1 d D U P . .
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'
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'
I I -0.4742 1.8119 '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'
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
C32 P2 C26 100.64(11) . . ?
C32 P2 C25 102.25(10) . . ?
C26 P2 C25 101.36(10) . . ?
C2 P1 C14 109.47(11) . . ?
C2 P1 C8 110.11(11) . . ?
C14 P1 C8 111.40(11) . . ?
C2 P1 C1 108.60(12) . . ?
C14 P1 C1 107.17(11) . . ?
C8 P1 C1 110.00(12) . . ?
C19 O1 C20 121.65(18) . . ?
C15 C14 C19 119.3(2) . . ?
C15 C14 P1 122.18(17) . . ?
C19 C14 P1 118.49(16) . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C7 C2 C3 120.4(2) . . ?
C7 C2 P1 119.50(19) . . ?
C3 C2 P1 120.02(19) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C8 C13 C12 119.2(3) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C18 C19 O1 123.6(2) . . ?
C18 C19 C14 121.1(2) . . ?
O1 C19 C14 115.1(2) . . ?
C24 C25 C20 117.0(2) . . ?
C24 C25 P2 126.39(17) . . ?
C20 C25 P2 116.31(17) . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
F1 C1 P1 109.29(17) . . ?
F1 C1 H1A 109.8 . . ?
P1 C1 H1A 109.8 . . ?
F1 C1 H1B 109.8 . . ?
P1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C21 C20 O1 122.5(2) . . ?
C21 C20 C25 123.1(2) . . ?
O1 C20 C25 114.22(19) . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C37 C32 C33 119.0(2) . . ?
C37 C32 P2 124.93(19) . . ?
C33 C32 P2 116.04(19) . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 121.2(2) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C31 C26 C27 118.6(2) . . ?
C31 C26 P2 116.71(18) . . ?
C27 C26 P2 124.68(19) . . ?
C17 C18 C19 118.7(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C32 C37 C36 120.3(3) . . ?
C32 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C26 C31 C30 120.5(2) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C29 C28 C27 120.2(3) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C6 C7 C2 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
C13 C8 C9 120.8(2) . . ?
C13 C8 P1 120.50(19) . . ?
C9 C8 P1 118.7(2) . . ?
C29 C30 C31 120.1(3) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C22 C21 C20 118.2(2) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C30 C29 C28 119.8(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C34 C33 C32 120.5(3) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C35 C36 C37 120.2(3) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C33 C34 C35 120.0(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 119.9(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
H210 O2 H211 103(3) . . ?
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
P2 C32 1.829(2) . ?
P2 C26 1.829(2) . ?
P2 C25 1.844(2) . ?
P1 C2 1.784(2) . ?
P1 C14 1.784(2) . ?
P1 C8 1.789(2) . ?
P1 C1 1.831(3) . ?
O1 C19 1.384(3) . ?
O1 C20 1.393(3) . ?
C14 C15 1.395(3) . ?
C14 C19 1.398(3) . ?
C11 C12 1.376(5) . ?
C11 C10 1.377(5) . ?
C11 H11 1.01(4) . ?
C22 C21 1.386(4) . ?
C22 C23 1.393(4) . ?
C22 H22 0.94(3) . ?
C2 C7 1.390(4) . ?
C2 C3 1.396(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.95(3) . ?
C13 C8 1.387(4) . ?
C13 C12 1.397(4) . ?
C13 H13 0.92(3) . ?
C19 C18 1.383(3) . ?
C25 C24 1.394(3) . ?
C25 C20 1.394(3) . ?
C16 C17 1.384(4) . ?
C16 H16 0.86(3) . ?
C1 F1 1.376(3) . ?
C1 H1A 0.94(2) . ?
C1 H1B 0.94(2) . ?
C20 C21 1.391(3) . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C12 H12 0.90(4) . ?
C32 C37 1.388(4) . ?
C32 C33 1.400(4) . ?
C23 C24 1.387(4) . ?
C23 H23 0.93(3) . ?
C24 H24 0.92(3) . ?
C26 C31 1.390(3) . ?
C26 C27 1.393(3) . ?
C18 H18 0.85(3) . ?
C37 C36 1.394(4) . ?
C37 H37 0.94(3) . ?
C3 C4 1.391(4) . ?
C3 H3 0.95(3) . ?
C31 C30 1.393(4) . ?
C31 H31 0.93(3) . ?
C28 C29 1.381(4) . ?
C28 C27 1.388(4) . ?
C28 H28 0.96(3) . ?
C7 C6 1.388(4) . ?
C7 H7 0.91(4) . ?
C8 C9 1.397(4) . ?
C30 C29 1.381(4) . ?
C30 H30 0.88(4) . ?
C27 H27 0.90(3) . ?
C21 H21 0.92(3) . ?
C29 H29 0.95(3) . ?
C33 C34 1.380(4) . ?
C33 H33 1.05(3) . ?
C4 C5 1.375(4) . ?
C4 H4 0.89(3) . ?
C9 C10 1.391(4) . ?
C9 H9 0.94(4) . ?
C36 C35 1.379(5) . ?
C36 H36 0.9500 . ?
C34 C35 1.393(5) . ?
C34 H34 0.99(4) . ?
C35 H35 0.93(4) . ?
C5 C6 1.383(5) . ?
C5 H5 0.92(4) . ?
C10 H10 0.92(4) . ?
C6 H6 0.94(4) . ?
O2 H210 0.89(2) . ?
O2 H211 0.88(2) . ?
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
C2 P1 C14 C15 3.8(2) . . . . ?
C8 P1 C14 C15 -118.2(2) . . . . ?
C1 P1 C14 C15 121.4(2) . . . . ?
C2 P1 C14 C19 -174.92(18) . . . . ?
C8 P1 C14 C19 63.1(2) . . . . ?
C1 P1 C14 C19 -57.3(2) . . . . ?
C14 P1 C2 C7 -95.3(2) . . . . ?
C8 P1 C2 C7 27.5(3) . . . . ?
C1 P1 C2 C7 148.0(2) . . . . ?
C14 P1 C2 C3 82.4(2) . . . . ?
C8 P1 C2 C3 -154.8(2) . . . . ?
C1 P1 C2 C3 -34.3(2) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?
P1 C14 C15 C16 -178.56(18) . . . . ?
C20 O1 C19 C18 -53.0(3) . . . . ?
C20 O1 C19 C14 132.3(2) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
P1 C14 C19 C18 178.82(18) . . . . ?
C15 C14 C19 O1 174.9(2) . . . . ?
P1 C14 C19 O1 -6.3(3) . . . . ?
C32 P2 C25 C24 2.2(2) . . . . ?
C26 P2 C25 C24 105.8(2) . . . . ?
C32 P2 C25 C20 176.02(18) . . . . ?
C26 P2 C25 C20 -80.30(19) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C2 P1 C1 F1 -50.7(2) . . . . ?
C14 P1 C1 F1 -168.89(17) . . . . ?
C8 P1 C1 F1 69.9(2) . . . . ?
C19 O1 C20 C21 -29.9(3) . . . . ?
C19 O1 C20 C25 155.6(2) . . . . ?
C24 C25 C20 C21 1.1(3) . . . . ?
P2 C25 C20 C21 -173.36(19) . . . . ?
C24 C25 C20 O1 175.6(2) . . . . ?
P2 C25 C20 O1 1.1(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C8 C13 C12 C11 1.6(4) . . . . ?
C26 P2 C32 C37 -33.2(2) . . . . ?
C25 P2 C32 C37 71.1(2) . . . . ?
C26 P2 C32 C33 145.4(2) . . . . ?
C25 P2 C32 C33 -110.4(2) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C20 C25 C24 C23 0.0(3) . . . . ?
P2 C25 C24 C23 173.8(2) . . . . ?
C32 P2 C26 C31 -76.5(2) . . . . ?
C25 P2 C26 C31 178.59(19) . . . . ?
C32 P2 C26 C27 103.5(2) . . . . ?
C25 P2 C26 C27 -1.4(2) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
O1 C19 C18 C17 -174.4(2) . . . . ?
C14 C19 C18 C17 0.0(4) . . . . ?
C33 C32 C37 C36 1.6(4) . . . . ?
P2 C32 C37 C36 -179.9(2) . . . . ?
C7 C2 C3 C4 -0.6(4) . . . . ?
P1 C2 C3 C4 -178.3(2) . . . . ?
C27 C26 C31 C30 -2.6(4) . . . . ?
P2 C26 C31 C30 177.3(2) . . . . ?
C3 C2 C7 C6 -0.7(5) . . . . ?
P1 C2 C7 C6 177.0(3) . . . . ?
C12 C13 C8 C9 -0.9(4) . . . . ?
C12 C13 C8 P1 179.46(19) . . . . ?
C2 P1 C8 C13 -105.1(2) . . . . ?
C14 P1 C8 C13 16.6(2) . . . . ?
C1 P1 C8 C13 135.2(2) . . . . ?
C2 P1 C8 C9 75.3(2) . . . . ?
C14 P1 C8 C9 -163.1(2) . . . . ?
C1 P1 C8 C9 -44.4(2) . . . . ?
C26 C31 C30 C29 1.6(4) . . . . ?
C29 C28 C27 C26 0.3(4) . . . . ?
C31 C26 C27 C28 1.7(4) . . . . ?
P2 C26 C27 C28 -178.3(2) . . . . ?
C23 C22 C21 C20 0.7(4) . . . . ?
O1 C20 C21 C22 -175.4(2) . . . . ?
C25 C20 C21 C22 -1.4(4) . . . . ?
C31 C30 C29 C28 0.5(4) . . . . ?
C27 C28 C29 C30 -1.4(4) . . . . ?
C37 C32 C33 C34 -1.2(4) . . . . ?
P2 C32 C33 C34 -179.8(2) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
P1 C8 C9 C10 179.2(2) . . . . ?
C32 C37 C36 C35 -0.5(4) . . . . ?
C32 C33 C34 C35 -0.2(5) . . . . ?
C37 C36 C35 C34 -0.9(4) . . . . ?
C33 C34 C35 C36 1.2(5) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
C12 C11 C10 C9 -0.6(5) . . . . ?
C8 C9 C10 C11 1.2(5) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C2 C7 C6 C5 0.7(5) . . . . ?
