# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Miluykov Vasili'
_publ_contact_author_email       MILUYKOV@IOPC.KNC.RU

_publ_section_title              
;
Phosphonium ionic liquids based
on bulky phosphines: synthesis, structure and properties
;
loop_
_publ_author_name
'Miluykov Vasili'
'Vadim Ermolaev'
'Sergey A. Katsyuba'
'Dmitry B. Krivolapov'
'R. Schmutzler'
;
O.Sinyashin
;
'Elena E. Zvereva'

# Attachment 'm52-revised.cif'

data_m52
_database_code_depnum_ccdc_archive 'CCDC 738385'
#TrackingRef 'm52-revised.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"'Decyl(tricyclohexyl)phosphonium terafluoroborate '"
_chemical_name_common            
"'Decyl(tricyclohexyl)phosphonium terafluoroborate '"
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H54 B F4 P'
_chemical_melting_point          ?
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         508.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
B B 0.0013 0.0007 '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'
C C 0.0033 0.0016 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   10.106(5)
_cell_length_b                   28.737(9)
_cell_length_c                   10.433(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.89(4)
_cell_angle_gamma                90.00
_cell_volume                     3019(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      16
_cell_measurement_theta_max      18
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Enraf-Nonius CAD4'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       \w\2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  7200
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6376
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0847
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         26.29
_reflns_number_total             6050
_reflns_number_gt                2857
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CAD4_(Enraf-Nonius,_1977)
_computing_cell_refinement       CAD4_(Enraf-Nonius,_1977)
_computing_data_reduction        process_MolEN_(Fair,_1990)
_computing_structure_solution    Direct_methods_(SIR,_Burla_et_al.,_1989)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1116P)^2^+0.4181P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6050
_refine_ls_number_parameters     360
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1834
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.2290
_refine_ls_wR_factor_gt          0.1780
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.2516(6) 0.0321(2) 0.2095(7) 0.0856(15) Uani 1 1 d . . .
C13 C 0.7685(3) 0.10990(11) 0.0893(3) 0.0525(8) Uani 1 1 d . . .
H13 H 0.7568 0.1430 0.1082 0.063 Uiso 1 1 calc R . .
C1 C 0.8193(3) 0.01877(11) 0.2218(3) 0.0541(8) Uani 1 1 d . . .
H1 H 0.8703 0.0166 0.1462 0.065 Uiso 1 1 calc R . .
C7 C 0.6355(3) 0.08902(11) 0.3251(3) 0.0545(8) Uani 1 1 d . . .
H7 H 0.5660 0.0702 0.2790 0.065 Uiso 1 1 calc R . .
C14 C 0.6470(4) 0.09551(14) 0.0007(3) 0.0660(10) Uani 1 1 d . . .
H141 H 0.6566 0.0635 -0.0266 0.079 Uiso 1 1 calc R . .
H124 H 0.5677 0.0977 0.0466 0.079 Uiso 1 1 calc R . .
C6 C 0.9070(4) -0.00309(13) 0.3334(4) 0.0730(11) Uani 1 1 d . . .
H61 H 0.9890 0.0144 0.3480 0.088 Uiso 1 1 calc R . .
H62 H 0.8613 -0.0019 0.4114 0.088 Uiso 1 1 calc R . .
C2 C 0.6934(4) -0.00980(13) 0.1896(4) 0.0775(11) Uani 1 1 d . . .
H21 H 0.6386 -0.0089 0.2616 0.093 Uiso 1 1 calc R . .
H22 H 0.6428 0.0035 0.1153 0.093 Uiso 1 1 calc R . .
C18 C 0.8951(4) 0.10645(13) 0.0168(3) 0.0641(10) Uani 1 1 d . . .
H181 H 0.9717 0.1161 0.0729 0.077 Uiso 1 1 calc R . .
H182 H 0.9087 0.0745 -0.0088 0.077 Uiso 1 1 calc R . .
C19 C 0.9289(3) 0.10495(12) 0.3348(3) 0.0599(9) Uani 1 1 d . . .
H191 H 0.9325 0.0918 0.4207 0.072 Uiso 1 1 calc R . .
H192 H 1.0074 0.0942 0.2961 0.072 Uiso 1 1 calc R . .
C20 C 0.9399(4) 0.15724(14) 0.3487(4) 0.0804(12) Uani 1 1 d . . .
H201 H 0.9426 0.1711 0.2641 0.097 Uiso 1 1 calc R . .
H202 H 0.8616 0.1690 0.3856 0.097 Uiso 1 1 calc R . .
C12 C 0.5850(4) 0.13943(12) 0.3219(4) 0.0646(10) Uani 1 1 d . . .
H121 H 0.6521 0.1595 0.3647 0.078 Uiso 1 1 calc R . .
H122 H 0.5693 0.1496 0.2333 0.078 Uiso 1 1 calc R . .
C10 C 0.4738(5) 0.12528(15) 0.5238(4) 0.0833(13) Uani 1 1 d . . .
H102 H 0.5366 0.1447 0.5750 0.100 Uiso 1 1 calc R . .
H101 H 0.3892 0.1269 0.5611 0.100 Uiso 1 1 calc R . .
C9 C 0.5223(4) 0.07579(15) 0.5278(4) 0.0830(12) Uani 1 1 d . . .
H91 H 0.4551 0.0559 0.4843 0.100 Uiso 1 1 calc R . .
H92 H 0.5363 0.0656 0.6166 0.100 Uiso 1 1 calc R . .
C11 C 0.4577(4) 0.14347(14) 0.3876(4) 0.0736(11) Uani 1 1 d . . .
H111 H 0.4307 0.1759 0.3887 0.088 Uiso 1 1 calc R . .
H112 H 0.3881 0.1261 0.3390 0.088 Uiso 1 1 calc R . .
C16 C 0.7593(5) 0.12556(16) -0.1879(4) 0.0838(12) Uani 1 1 d . . .
H161 H 0.7693 0.0946 -0.2226 0.101 Uiso 1 1 calc R . .
H162 H 0.7504 0.1472 -0.2594 0.101 Uiso 1 1 calc R . .
C5 C 0.9379(4) -0.05314(14) 0.3018(4) 0.0807(12) Uani 1 1 d . . .
H51 H 0.9911 -0.0539 0.2287 0.097 Uiso 1 1 calc R . .
H52 H 0.9896 -0.0671 0.3744 0.097 Uiso 1 1 calc R . .
C17 C 0.8806(4) 0.13760(13) -0.1019(4) 0.0729(11) Uani 1 1 d . . .
H171 H 0.8753 0.1698 -0.0752 0.087 Uiso 1 1 calc R . .
H172 H 0.9586 0.1343 -0.1493 0.087 Uiso 1 1 calc R . .
C15 C 0.6340(4) 0.12729(16) -0.1160(4) 0.0818(12) Uani 1 1 d . . .
H151 H 0.6188 0.1590 -0.0887 0.098 Uiso 1 1 calc R . .
H152 H 0.5581 0.1177 -0.1732 0.098 Uiso 1 1 calc R . .
C8 C 0.6509(4) 0.07087(14) 0.4640(3) 0.0747(11) Uani 1 1 d . . .
H81 H 0.6769 0.0384 0.4639 0.090 Uiso 1 1 calc R . .
H82 H 0.7206 0.0882 0.5128 0.090 Uiso 1 1 calc R . .
C22 C 1.0753(5) 0.22264(16) 0.4545(6) 0.1151(18) Uani 1 1 d . B .
H221 H 1.0865 0.2377 0.3729 0.138 Uiso 1 1 calc R . .
H222 H 0.9934 0.2342 0.4847 0.138 Uiso 1 1 calc R . .
C4 C 0.8139(5) -0.08111(15) 0.2711(5) 0.0920(14) Uani 1 1 d . . .
H41 H 0.8375 -0.1127 0.2493 0.110 Uiso 1 1 calc R . .
H42 H 0.7638 -0.0824 0.3463 0.110 Uiso 1 1 calc R . .
C3 C 0.7294(5) -0.06011(15) 0.1612(5) 0.0973(15) Uani 1 1 d . . .
H32 H 0.6488 -0.0782 0.1451 0.117 Uiso 1 1 calc R . .
H31 H 0.7770 -0.0611 0.0843 0.117 Uiso 1 1 calc R . .
C21 C 1.0608(4) 0.17171(14) 0.4317(5) 0.0932(14) Uani 1 1 d . . .
H211 H 1.0596 0.1563 0.5143 0.112 Uiso 1 1 calc R . .
H212 H 1.1386 0.1607 0.3923 0.112 Uiso 1 1 calc R . .
P1 P 0.78609(8) 0.08042(3) 0.24345(8) 0.0504(3) Uani 1 1 d . . .
F3 F 0.1695(10) 0.0070(3) 0.1267(11) 0.127(4) Uani 0.629(13) 1 d P A 1
F4 F 0.2469(13) 0.0178(7) 0.3273(10) 0.189(7) Uani 0.629(13) 1 d P A 1
F1 F 0.3684(7) 0.0292(5) 0.1717(12) 0.150(5) Uani 0.629(13) 1 d P A 1
F2 F 0.2075(9) 0.0763(2) 0.1960(11) 0.138(3) Uani 0.629(13) 1 d P A 1
F1A F 0.317(3) -0.0057(8) 0.232(3) 0.296(15) Uani 0.371(13) 1 d P A 2
F2A F 0.1411(18) 0.0269(10) 0.1378(17) 0.183(12) Uani 0.371(13) 1 d P A 2
F4A F 0.348(3) 0.0594(11) 0.163(2) 0.211(15) Uani 0.371(13) 1 d P A 2
F5A F 0.2212(15) 0.0471(10) 0.325(2) 0.187(15) Uani 0.371(13) 1 d P A 2
C23 C 1.1858(7) 0.2369(2) 0.5469(8) 0.140(2) Uani 1 1 d D . .
H231 H 1.2674 0.2313 0.5067 0.168 Uiso 0.454(9) 1 calc PR B 1
H232 H 1.1788 0.2702 0.5584 0.168 Uiso 0.454(9) 1 calc PR B 1
H233 H 1.2675 0.2249 0.5170 0.168 Uiso 0.546(9) 1 d PR B 2
H234 H 1.1914 0.2705 0.5445 0.168 Uiso 0.546(9) 1 d PR B 2
C24 C 1.202(4) 0.2163(6) 0.6727(17) 0.164(8) Uani 0.454(9) 1 d PD B 1
H24A H 1.1199 0.1994 0.6824 0.196 Uiso 0.454(9) 1 calc PR B 1
H24B H 1.2706 0.1930 0.6692 0.196 Uiso 0.454(9) 1 calc PR B 1
C27 C 1.258(5) 0.2321(11) 1.024(3) 0.283(12) Uani 0.454(9) 1 d PD B 1
H27A H 1.3186 0.2569 1.0536 0.339 Uiso 0.454(9) 1 calc PR B 1
H27B H 1.1693 0.2449 1.0139 0.339 Uiso 0.454(9) 1 calc PR B 1
C25 C 1.230(4) 0.2402(5) 0.7886(19) 0.187(6) Uani 0.454(9) 1 d PD B 1
H25A H 1.1479 0.2522 0.8163 0.224 Uiso 0.454(9) 1 calc PR B 1
H25B H 1.2857 0.2667 0.7718 0.224 Uiso 0.454(9) 1 calc PR B 1
C26 C 1.2963(19) 0.2141(9) 0.894(2) 0.173(6) Uani 0.454(9) 1 d PD B 1
H26A H 1.3917 0.2166 0.8910 0.207 Uiso 0.454(9) 1 calc PR B 1
H26B H 1.2722 0.1816 0.8852 0.207 Uiso 0.454(9) 1 calc PR B 1
C28 C 1.263(4) 0.1957(9) 1.121(3) 0.264(10) Uani 0.454(9) 1 d PD B 1
H28A H 1.2582 0.2094 1.2042 0.396 Uiso 0.454(9) 1 calc PR B 1
H28B H 1.3450 0.1788 1.1194 0.396 Uiso 0.454(9) 1 calc PR B 1
H28C H 1.1897 0.1749 1.1028 0.396 Uiso 0.454(9) 1 calc PR B 1
C26A C 1.2123(16) 0.2192(8) 0.9223(17) 0.173(6) Uani 0.546(9) 1 d PD B 2
H26C H 1.1706 0.2484 0.9430 0.207 Uiso 0.546(9) 1 calc PR B 2
H26D H 1.1456 0.1950 0.9235 0.207 Uiso 0.546(9) 1 calc PR B 2
C24A C 1.157(3) 0.2315(6) 0.6832(15) 0.164(8) Uani 0.546(9) 1 d PD B 2
H24C H 1.1111 0.2597 0.7051 0.196 Uiso 0.546(9) 1 calc PR B 2
H24D H 1.0926 0.2065 0.6844 0.196 Uiso 0.546(9) 1 calc PR B 2
C25A C 1.255(3) 0.2226(4) 0.7897(19) 0.187(6) Uani 0.546(9) 1 d PD B 2
H25C H 1.3209 0.2471 0.7898 0.224 Uiso 0.546(9) 1 calc PR B 2
H25D H 1.2993 0.1937 0.7716 0.224 Uiso 0.546(9) 1 calc PR B 2
C27A C 1.318(3) 0.2092(11) 1.023(2) 0.283(12) Uani 0.546(9) 1 d PD B 2
H27C H 1.3285 0.1758 1.0328 0.339 Uiso 0.546(9) 1 calc PR B 2
H27D H 1.4015 0.2219 0.9985 0.339 Uiso 0.546(9) 1 calc PR B 2
C28A C 1.286(3) 0.2297(8) 1.143(2) 0.264(10) Uani 0.546(9) 1 d PD B 2
H28D H 1.3390 0.2153 1.2132 0.396 Uiso 0.546(9) 1 calc PR B 2
H28E H 1.1937 0.2248 1.1539 0.396 Uiso 0.546(9) 1 calc PR B 2
H28F H 1.3044 0.2624 1.1426 0.396 Uiso 0.546(9) 1 calc PR B 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.069(4) 0.086(4) 0.101(5) -0.007(4) -0.001(3) 0.004(3)
C13 0.055(2) 0.052(2) 0.0505(19) 0.0032(15) 0.0080(16) 0.0018(15)
C1 0.059(2) 0.053(2) 0.0502(19) -0.0031(16) 0.0052(16) 0.0042(16)
C7 0.0515(19) 0.062(2) 0.0501(19) -0.0014(16) 0.0021(15) 0.0022(16)
C14 0.061(2) 0.084(3) 0.052(2) 0.0053(19) 0.0001(18) -0.0069(19)
C6 0.085(3) 0.066(3) 0.067(2) 0.0020(19) 0.001(2) 0.015(2)
C2 0.069(3) 0.059(2) 0.103(3) -0.003(2) 0.002(2) -0.0090(19)
C18 0.068(2) 0.064(2) 0.061(2) 0.0012(18) 0.0119(18) 0.0015(18)
C19 0.058(2) 0.061(2) 0.059(2) -0.0002(17) -0.0004(17) -0.0018(17)
C20 0.071(3) 0.072(3) 0.096(3) -0.018(2) -0.007(2) -0.006(2)
C12 0.068(2) 0.063(2) 0.065(2) -0.0029(18) 0.0154(19) 0.0090(18)
C10 0.085(3) 0.092(3) 0.077(3) -0.009(2) 0.032(2) 0.008(2)
C9 0.089(3) 0.096(3) 0.068(3) 0.011(2) 0.032(2) 0.005(2)
C11 0.067(2) 0.070(3) 0.085(3) -0.009(2) 0.018(2) 0.0116(19)
C16 0.101(3) 0.093(3) 0.058(2) 0.018(2) 0.011(2) 0.003(3)
C5 0.096(3) 0.066(3) 0.080(3) 0.011(2) 0.007(2) 0.023(2)
C17 0.088(3) 0.068(2) 0.066(2) 0.011(2) 0.026(2) -0.006(2)
C15 0.079(3) 0.107(3) 0.058(2) 0.013(2) -0.005(2) 0.005(2)
C8 0.090(3) 0.084(3) 0.054(2) 0.0084(19) 0.024(2) 0.014(2)
C22 0.101(4) 0.072(3) 0.165(5) -0.004(3) -0.035(4) -0.013(3)
C4 0.099(3) 0.058(2) 0.125(4) 0.011(3) 0.040(3) 0.002(2)
C3 0.092(3) 0.063(3) 0.134(4) -0.009(3) -0.009(3) -0.018(2)
C21 0.083(3) 0.067(3) 0.124(4) -0.012(3) -0.022(3) -0.009(2)
P1 0.0512(5) 0.0542(5) 0.0456(5) -0.0024(4) 0.0040(3) 0.0011(4)
F3 0.122(9) 0.117(5) 0.140(6) -0.042(5) 0.003(5) -0.048(5)
F4 0.162(9) 0.298(17) 0.102(8) 0.078(9) -0.018(6) -0.010(9)
F1 0.052(4) 0.208(12) 0.192(9) -0.039(9) 0.022(4) 0.010(6)
F2 0.124(6) 0.113(5) 0.175(8) -0.041(4) 0.001(5) 0.023(4)
F1A 0.40(4) 0.174(17) 0.32(3) 0.078(16) 0.10(3) 0.151(19)
F2A 0.061(6) 0.37(3) 0.117(12) 0.105(17) -0.010(7) 0.003(14)
F4A 0.21(3) 0.28(3) 0.143(11) 0.004(16) 0.001(13) -0.17(2)
F5A 0.078(7) 0.30(3) 0.19(2) -0.14(2) 0.046(10) -0.020(11)
C23 0.146(5) 0.091(4) 0.179(7) -0.033(4) -0.003(5) -0.021(4)
C24 0.26(2) 0.041(10) 0.175(9) -0.013(7) -0.080(10) -0.005(11)
C27 0.41(4) 0.25(3) 0.199(15) 0.054(18) 0.08(2) 0.14(2)
C25 0.338(18) 0.035(9) 0.184(9) -0.045(8) 0.004(11) 0.018(12)
C26 0.122(12) 0.235(13) 0.153(11) 0.011(10) -0.031(12) -0.026(14)
C28 0.40(3) 0.20(2) 0.173(13) 0.053(17) -0.054(15) -0.08(2)
C26A 0.122(12) 0.235(13) 0.153(11) 0.011(10) -0.031(12) -0.026(14)
C24A 0.26(2) 0.041(10) 0.175(9) -0.013(7) -0.080(10) -0.005(11)
C25A 0.338(18) 0.035(9) 0.184(9) -0.045(8) 0.004(11) 0.018(12)
C27A 0.41(4) 0.25(3) 0.199(15) 0.054(18) 0.08(2) 0.14(2)
C28A 0.40(3) 0.20(2) 0.173(13) 0.053(17) -0.054(15) -0.08(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
B1 F1 1.280(10) . ?
B1 F1A 1.285(16) . ?
B1 F2A 1.299(17) . ?
B1 F4 1.301(10) . ?
B1 F5A 1.342(18) . ?
B1 F2 1.349(8) . ?
B1 F3 1.353(10) . ?
B1 F4A 1.366(18) . ?
C13 C14 1.529(5) . ?
C13 C18 1.544(5) . ?
C13 P1 1.813(3) . ?
C13 H13 0.9800 . ?
C1 C2 1.527(5) . ?
C1 C6 1.536(5) . ?
C1 P1 1.821(3) . ?
C1 H1 0.9800 . ?
C7 C8 1.535(5) . ?
C7 C12 1.535(5) . ?
C7 P1 1.823(3) . ?
C7 H7 0.9800 . ?
C14 C15 1.519(5) . ?
C14 H141 0.9700 . ?
C14 H124 0.9700 . ?
C6 C5 1.514(5) . ?
C6 H61 0.9700 . ?
C6 H62 0.9700 . ?
C2 C3 1.526(6) . ?
C2 H21 0.9700 . ?
C2 H22 0.9700 . ?
C18 C17 1.525(5) . ?
C18 H181 0.9700 . ?
C18 H182 0.9700 . ?
C19 C20 1.513(5) . ?
C19 P1 1.804(3) . ?
C19 H191 0.9700 . ?
C19 H192 0.9700 . ?
C20 C21 1.495(5) . ?
C20 H201 0.9700 . ?
C20 H202 0.9700 . ?
C12 C11 1.513(5) . ?
C12 H121 0.9700 . ?
C12 H122 0.9700 . ?
C10 C9 1.504(6) . ?
C10 C11 1.510(6) . ?
C10 H102 0.9700 . ?
C10 H101 0.9700 . ?
C9 C8 1.517(5) . ?
C9 H91 0.9700 . ?
C9 H92 0.9700 . ?
C11 H111 0.9700 . ?
C11 H112 0.9700 . ?
C16 C17 1.497(6) . ?
C16 C15 1.527(6) . ?
C16 H161 0.9700 . ?
C16 H162 0.9700 . ?
C5 C4 1.500(6) . ?
C5 H51 0.9700 . ?
C5 H52 0.9700 . ?
C17 H171 0.9700 . ?
C17 H172 0.9700 . ?
C15 H151 0.9700 . ?
C15 H152 0.9700 . ?
C8 H81 0.9700 . ?
C8 H82 0.9700 . ?
C22 C23 1.469(8) . ?
C22 C21 1.488(6) . ?
C22 H221 0.9700 . ?
C22 H222 0.9700 . ?
C4 C3 1.497(6) . ?
C4 H41 0.9700 . ?
C4 H42 0.9700 . ?
C3 H32 0.9700 . ?
C3 H31 0.9700 . ?
C21 H211 0.9700 . ?
C21 H212 0.9700 . ?
C23 C24 1.435(16) . ?
C23 C24A 1.484(16) . ?
C23 H231 0.9700 . ?
C23 H232 0.9700 . ?
C23 H233 0.9700 . ?
C23 H234 0.9700 . ?
C24 C25 1.399(17) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C27 C28 1.449(19) . ?
C27 C26 1.532(18) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C25 C26 1.446(18) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C26A C27A 1.462(18) . ?
C26A C25A 1.486(17) . ?
C26A H26C 0.9700 . ?
C26A H26D 0.9700 . ?
C24A C25A 1.446(17) . ?
C24A H24C 0.9700 . ?
C24A H24D 0.9700 . ?
C25A H25C 0.9700 . ?
C25A H25D 0.9700 . ?
C27A C28A 1.450(18) . ?
C27A H27C 0.9700 . ?
C27A H27D 0.9700 . ?
C28A H28D 0.9600 . ?
C28A H28E 0.9600 . ?
C28A H28F 0.9600 . ?

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
F1 B1 F1A 61.8(14) . . ?
F1 B1 F2A 125.8(13) . . ?
F1A B1 F2A 114.5(17) . . ?
F1 B1 F4 112.3(10) . . ?
F1A B1 F4 67.4(11) . . ?
F2A B1 F4 114.2(10) . . ?
F1 B1 F5A 125.9(10) . . ?
F1A B1 F5A 104.9(15) . . ?
F2A B1 F5A 107.7(13) . . ?
F4 B1 F5A 39.0(12) . . ?
F1 B1 F2 109.5(8) . . ?
F1A B1 F2 167.5(17) . . ?
F2A B1 F2 77.8(13) . . ?
F4 B1 F2 111.0(9) . . ?
F5A B1 F2 72.1(13) . . ?
F1 B1 F3 107.4(9) . . ?
F1A B1 F3 87.0(16) . . ?
F2A B1 F3 28.5(13) . . ?
F4 B1 F3 111.4(9) . . ?
F5A B1 F3 124.8(10) . . ?
F2 B1 F3 104.8(7) . . ?
F1 B1 F4A 39.4(12) . . ?
F1A B1 F4A 100.4(16) . . ?
F2A B1 F4A 117.7(14) . . ?
F4 B1 F4A 126.8(12) . . ?
F5A B1 F4A 110.9(14) . . ?
F2 B1 F4A 70.2(14) . . ?
F3 B1 F4A 119.7(11) . . ?
C14 C13 C18 110.0(3) . . ?
C14 C13 P1 115.0(2) . . ?
C18 C13 P1 112.5(2) . . ?
C14 C13 H13 106.2 . . ?
C18 C13 H13 106.2 . . ?
P1 C13 H13 106.2 . . ?
C2 C1 C6 111.3(3) . . ?
C2 C1 P1 113.1(2) . . ?
C6 C1 P1 113.8(2) . . ?
C2 C1 H1 106.0 . . ?
C6 C1 H1 106.0 . . ?
P1 C1 H1 106.0 . . ?
C8 C7 C12 110.4(3) . . ?
C8 C7 P1 111.9(2) . . ?
C12 C7 P1 114.0(2) . . ?
C8 C7 H7 106.7 . . ?
C12 C7 H7 106.7 . . ?
P1 C7 H7 106.7 . . ?
C15 C14 C13 109.4(3) . . ?
C15 C14 H141 109.8 . . ?
C13 C14 H141 109.8 . . ?
C15 C14 H124 109.8 . . ?
C13 C14 H124 109.8 . . ?
H141 C14 H124 108.2 . . ?
C5 C6 C1 109.9(3) . . ?
C5 C6 H61 109.7 . . ?
C1 C6 H61 109.7 . . ?
C5 C6 H62 109.7 . . ?
C1 C6 H62 109.7 . . ?
H61 C6 H62 108.2 . . ?
C3 C2 C1 110.1(3) . . ?
C3 C2 H21 109.6 . . ?
C1 C2 H21 109.6 . . ?
C3 C2 H22 109.6 . . ?
C1 C2 H22 109.6 . . ?
H21 C2 H22 108.2 . . ?
C17 C18 C13 109.5(3) . . ?
C17 C18 H181 109.8 . . ?
C13 C18 H181 109.8 . . ?
C17 C18 H182 109.8 . . ?
C13 C18 H182 109.8 . . ?
H181 C18 H182 108.2 . . ?
C20 C19 P1 119.2(3) . . ?
C20 C19 H191 107.5 . . ?
P1 C19 H191 107.5 . . ?
C20 C19 H192 107.5 . . ?
P1 C19 H192 107.5 . . ?
H191 C19 H192 107.0 . . ?
C21 C20 C19 112.4(3) . . ?
C21 C20 H201 109.1 . . ?
C19 C20 H201 109.1 . . ?
C21 C20 H202 109.1 . . ?
C19 C20 H202 109.1 . . ?
H201 C20 H202 107.9 . . ?
C11 C12 C7 110.9(3) . . ?
C11 C12 H121 109.5 . . ?
C7 C12 H121 109.5 . . ?
C11 C12 H122 109.5 . . ?
C7 C12 H122 109.5 . . ?
H121 C12 H122 108.1 . . ?
C9 C10 C11 111.2(3) . . ?
C9 C10 H102 109.4 . . ?
C11 C10 H102 109.4 . . ?
C9 C10 H101 109.4 . . ?
C11 C10 H101 109.4 . . ?
H102 C10 H101 108.0 . . ?
C10 C9 C8 111.4(3) . . ?
C10 C9 H91 109.3 . . ?
C8 C9 H91 109.3 . . ?
C10 C9 H92 109.3 . . ?
C8 C9 H92 109.3 . . ?
H91 C9 H92 108.0 . . ?
C10 C11 C12 111.9(3) . . ?
C10 C11 H111 109.2 . . ?
C12 C11 H111 109.2 . . ?
C10 C11 H112 109.2 . . ?
C12 C11 H112 109.2 . . ?
H111 C11 H112 107.9 . . ?
C17 C16 C15 111.7(3) . . ?
C17 C16 H161 109.3 . . ?
C15 C16 H161 109.3 . . ?
C17 C16 H162 109.3 . . ?
C15 C16 H162 109.3 . . ?
H161 C16 H162 107.9 . . ?
C4 C5 C6 111.8(4) . . ?
C4 C5 H51 109.3 . . ?
C6 C5 H51 109.3 . . ?
C4 C5 H52 109.3 . . ?
C6 C5 H52 109.3 . . ?
H51 C5 H52 107.9 . . ?
C16 C17 C18 111.6(3) . . ?
C16 C17 H171 109.3 . . ?
C18 C17 H171 109.3 . . ?
C16 C17 H172 109.3 . . ?
C18 C17 H172 109.3 . . ?
H171 C17 H172 108.0 . . ?
C14 C15 C16 110.8(3) . . ?
C14 C15 H151 109.5 . . ?
C16 C15 H151 109.5 . . ?
C14 C15 H152 109.5 . . ?
C16 C15 H152 109.5 . . ?
H151 C15 H152 108.1 . . ?
C9 C8 C7 111.2(3) . . ?
C9 C8 H81 109.4 . . ?
C7 C8 H81 109.4 . . ?
C9 C8 H82 109.4 . . ?
C7 C8 H82 109.4 . . ?
H81 C8 H82 108.0 . . ?
C23 C22 C21 116.0(4) . . ?
C23 C22 H221 108.3 . . ?
C21 C22 H221 108.3 . . ?
C23 C22 H222 108.3 . . ?
C21 C22 H222 108.3 . . ?
H221 C22 H222 107.4 . . ?
C3 C4 C5 111.0(4) . . ?
C3 C4 H41 109.4 . . ?
C5 C4 H41 109.4 . . ?
C3 C4 H42 109.4 . . ?
C5 C4 H42 109.4 . . ?
H41 C4 H42 108.0 . . ?
C4 C3 C2 111.3(4) . . ?
C4 C3 H32 109.4 . . ?
C2 C3 H32 109.4 . . ?
C4 C3 H31 109.4 . . ?
C2 C3 H31 109.4 . . ?
H32 C3 H31 108.0 . . ?
C22 C21 C20 115.5(4) . . ?
C22 C21 H211 108.4 . . ?
C20 C21 H211 108.4 . . ?
C22 C21 H212 108.4 . . ?
C20 C21 H212 108.4 . . ?
H211 C21 H212 107.5 . . ?
C19 P1 C13 107.41(16) . . ?
C19 P1 C1 107.35(16) . . ?
C13 P1 C1 110.48(16) . . ?
C19 P1 C7 111.25(16) . . ?
C13 P1 C7 109.19(15) . . ?
C1 P1 C7 111.09(15) . . ?
C24 C23 C22 120.3(17) . . ?
C24 C23 C24A 25.4(17) . . ?
C22 C23 C24A 113.5(13) . . ?
C24 C23 H231 107.3 . . ?
C22 C23 H231 107.3 . . ?
C24A C23 H231 129.9 . . ?
C24 C23 H232 107.3 . . ?
C22 C23 H232 107.3 . . ?
C24A C23 H232 87.8 . . ?
H231 C23 H232 106.9 . . ?
C24 C23 H233 96.8 . . ?
C22 C23 H233 108.1 . . ?
C24A C23 H233 120.9 . . ?
H231 C23 H233 12.6 . . ?
H232 C23 H233 117.6 . . ?
C24 C23 H234 115.6 . . ?
C22 C23 H234 107.6 . . ?
C24A C23 H234 98.4 . . ?
H231 C23 H234 95.7 . . ?
H232 C23 H234 11.9 . . ?
H233 C23 H234 107.0 . . ?
C25 C24 C23 126.0(17) . . ?
C25 C24 H24A 105.8 . . ?
C23 C24 H24A 105.8 . . ?
C25 C24 H24B 105.8 . . ?
C23 C24 H24B 105.8 . . ?
H24A C24 H24B 106.2 . . ?
C28 C27 C26 112(2) . . ?
C28 C27 H27A 109.2 . . ?
C26 C27 H27A 109.2 . . ?
C28 C27 H27B 109.2 . . ?
C26 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C24 C25 C26 117.0(17) . . ?
C24 C25 H25A 108.1 . . ?
C26 C25 H25A 108.1 . . ?
C24 C25 H25B 108.1 . . ?
C26 C25 H25B 108.1 . . ?
H25A C25 H25B 107.3 . . ?
C25 C26 C27 112(2) . . ?
C25 C26 H26A 109.3 . . ?
C27 C26 H26A 109.3 . . ?
C25 C26 H26B 109.3 . . ?
C27 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27A C26A C25A 115.4(19) . . ?
C27A C26A H26C 108.4 . . ?
C25A C26A H26C 108.4 . . ?
C27A C26A H26D 108.4 . . ?
C25A C26A H26D 108.4 . . ?
H26C C26A H26D 107.5 . . ?
C25A C24A C23 125(2) . . ?
C25A C24A H24C 106.0 . . ?
C23 C24A H24C 106.0 . . ?
C25A C24A H24D 106.0 . . ?
C23 C24A H24D 106.0 . . ?
H24C C24A H24D 106.3 . . ?
C24A C25A C26A 120(2) . . ?
C24A C25A H25C 107.4 . . ?
C26A C25A H25C 107.4 . . ?
C24A C25A H25D 107.4 . . ?
C26A C25A H25D 107.4 . . ?
H25C C25A H25D 107.0 . . ?
C28A C27A C26A 109.7(19) . . ?
C28A C27A H27C 109.7 . . ?
C26A C27A H27C 109.7 . . ?
C28A C27A H27D 109.7 . . ?
C26A C27A H27D 109.7 . . ?
H27C C27A H27D 108.2 . . ?
C27A C28A H28D 109.5 . . ?
C27A C28A H28E 109.5 . . ?
H28D C28A H28E 109.5 . . ?
C27A C28A H28F 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.29
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048


data_m58_fin
_database_code_depnum_ccdc_archive 'CCDC 738493'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'tri(tretbutyl)decylphosphonium tetrafluoroborate '
_chemical_name_common            
'tri(tretbutyl)decylphosphonium tetrafluoroborate'
_chemical_formula_moiety         'C22 H48 P, B F4'
_chemical_formula_sum            'C22 H48 B F4 P'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         430.38

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c c n'
_symmetry_int_tables_number      56
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   17.819(3)
_cell_length_b                   22.858(3)
_cell_length_c                   12.7497(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5193.3(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2053
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      16.56
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              SmartApex2
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37416
_diffrn_reflns_av_R_equivalents  0.1603
_diffrn_reflns_av_sigmaI/netI    0.1091
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5105
_reflns_number_gt                1836
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0137P)^2^+16.5315P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5105
_refine_ls_number_parameters     281
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.2376
_refine_ls_R_factor_gt           0.0974
_refine_ls_wR_factor_ref         0.2099
_refine_ls_wR_factor_gt          0.1567
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.010

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.58699(9) 0.60666(6) 0.72239(12) 0.0581(4) Uani 1 1 d . . .
B1 B 0.6234(5) 0.6233(5) 0.2232(8) 0.082(3) Uani 1 1 d . . .
C14 C 0.6694(4) 0.5271(3) 0.5829(5) 0.089(2) Uani 1 1 d . . .
H14A H 0.6240 0.5048 0.5697 0.106 Uiso 1 1 calc R . .
H14B H 0.6739 0.5564 0.5283 0.106 Uiso 1 1 calc R . .
C16 C 0.7393(4) 0.4522(3) 0.4783(5) 0.099(2) Uani 1 1 d . . .
H16A H 0.6949 0.4278 0.4738 0.118 Uiso 1 1 calc R . .
H16B H 0.7380 0.4791 0.4196 0.118 Uiso 1 1 calc R . .
F4 F 0.6669(3) 0.6565(3) 0.1652(4) 0.167(2) Uani 1 1 d . . .
C10 C 0.6201(4) 0.6438(3) 0.8439(5) 0.089(2) Uani 1 1 d . . .
C13 C 0.6630(3) 0.5575(3) 0.6898(4) 0.0718(18) Uani 1 1 d . . .
H13A H 0.7092 0.5793 0.6998 0.086 Uiso 1 1 calc R . .
H13B H 0.6627 0.5268 0.7424 0.086 Uiso 1 1 calc R . .
C1 C 0.5016(4) 0.5602(3) 0.7507(6) 0.096(2) Uani 1 1 d . . .
C12 C 0.6626(4) 0.6016(3) 0.9156(5) 0.108(3) Uani 1 1 d . . .
H12A H 0.6801 0.6222 0.9764 0.162 Uiso 1 1 calc R . .
H12B H 0.7046 0.5855 0.8784 0.162 Uiso 1 1 calc R . .
H12C H 0.6297 0.5705 0.9370 0.162 Uiso 1 1 calc R . .
C4 C 0.4287(4) 0.5976(3) 0.7524(6) 0.119(3) Uani 1 1 d . . .
H4A H 0.3867 0.5730 0.7695 0.179 Uiso 1 1 calc R . .
H4B H 0.4210 0.6148 0.6846 0.179 Uiso 1 1 calc R . .
H4C H 0.4333 0.6279 0.8041 0.179 Uiso 1 1 calc R . .
C15 C 0.7356(4) 0.4871(3) 0.5788(5) 0.085(2) Uani 1 1 d . . .
H15A H 0.7334 0.4604 0.6378 0.102 Uiso 1 1 calc R . .
H15B H 0.7811 0.5101 0.5856 0.102 Uiso 1 1 calc R . .
C3 C 0.5119(5) 0.5286(3) 0.8596(6) 0.134(3) Uani 1 1 d . . .
H3A H 0.4675 0.5065 0.8757 0.201 Uiso 1 1 calc R . .
H3B H 0.5202 0.5572 0.9134 0.201 Uiso 1 1 calc R . .
H3C H 0.5543 0.5027 0.8561 0.201 Uiso 1 1 calc R . .
C2 C 0.4922(4) 0.5121(3) 0.6686(6) 0.116(3) Uani 1 1 d . . .
H2A H 0.5334 0.4852 0.6735 0.175 Uiso 1 1 calc R . .
H2B H 0.4912 0.5292 0.5999 0.175 Uiso 1 1 calc R . .
H2C H 0.4460 0.4916 0.6809 0.175 Uiso 1 1 calc R . .
F3 F 0.5856(5) 0.6598(3) 0.2847(5) 0.253(4) Uani 1 1 d . . .
C5 C 0.5717(4) 0.6581(3) 0.6119(5) 0.089(2) Uani 1 1 d . . .
C9 C 0.5562(4) 0.6728(3) 0.9059(5) 0.097(2) Uani 1 1 d . . .
H9A H 0.5205 0.6436 0.9268 0.145 Uiso 1 1 calc R . .
H9B H 0.5319 0.7014 0.8626 0.145 Uiso 1 1 calc R . .
H9C H 0.5764 0.6915 0.9672 0.145 Uiso 1 1 calc R . .
F2 F 0.6536(3) 0.5869(3) 0.2804(6) 0.212(3) Uani 1 1 d . . .
C8 C 0.5270(4) 0.7131(3) 0.6473(6) 0.110(3) Uani 1 1 d . . .
H8A H 0.5195 0.7385 0.5883 0.165 Uiso 1 1 calc R . .
H8B H 0.5547 0.7334 0.7006 0.165 Uiso 1 1 calc R . .
H8C H 0.4792 0.7012 0.6748 0.165 Uiso 1 1 calc R . .
C17 C 0.8062(4) 0.4144(3) 0.4671(6) 0.111(3) Uani 1 1 d . . .
H17A H 0.8076 0.3868 0.5249 0.134 Uiso 1 1 calc R . .
H17B H 0.8510 0.4384 0.4711 0.134 Uiso 1 1 calc R . .
F1 F 0.5697(4) 0.6014(3) 0.1657(6) 0.237(4) Uani 1 1 d . . .
C6 C 0.5271(4) 0.6254(3) 0.5202(5) 0.116(3) Uani 1 1 d . . .
H6A H 0.4802 0.6109 0.5470 0.174 Uiso 1 1 calc R . .
H6B H 0.5565 0.5932 0.4947 0.174 Uiso 1 1 calc R . .
H6C H 0.5176 0.6523 0.4639 0.174 Uiso 1 1 calc R . .
C18 C 0.8064(5) 0.3798(4) 0.3606(7) 0.144(4) Uani 1 1 d . A .
H18A H 0.7645 0.3528 0.3609 0.172 Uiso 1 1 calc R . .
H18B H 0.7981 0.4074 0.3040 0.172 Uiso 1 1 calc R . .
C19 C 0.8707(6) 0.3488(5) 0.3391(8) 0.171(4) Uani 1 1 d D . .
H191 H 0.8879 0.3315 0.4043 0.256 Uiso 0.59(2) 1 calc PR A 1
H192 H 0.9088 0.3765 0.3172 0.256 Uiso 0.59(2) 1 calc PR A 1
H193 H 0.8708 0.3143 0.3834 0.256 Uiso 0.41(2) 1 d PR A 2
H194 H 0.9128 0.3728 0.3609 0.256 Uiso 0.41(2) 1 d PR A 2
C11 C 0.6787(4) 0.6940(3) 0.8107(7) 0.127(3) Uani 1 1 d . . .
H11A H 0.6960 0.7140 0.8723 0.190 Uiso 1 1 calc R . .
H11B H 0.6544 0.7214 0.7648 0.190 Uiso 1 1 calc R . .
H11C H 0.7206 0.6766 0.7752 0.190 Uiso 1 1 calc R . .
C20 C 0.8677(17) 0.3007(7) 0.2578(12) 0.152(11) Uani 0.59(2) 1 d PD A 1
H20A H 0.9163 0.2817 0.2543 0.183 Uiso 0.59(2) 1 calc PR A 1
H20B H 0.8313 0.2716 0.2797 0.183 Uiso 0.59(2) 1 calc PR A 1
C21 C 0.8474(17) 0.3218(7) 0.1524(11) 0.158(9) Uani 0.59(2) 1 d PDU A 1
H21A H 0.8790 0.3547 0.1336 0.190 Uiso 0.59(2) 1 calc PR A 1
H21B H 0.7956 0.3348 0.1522 0.190 Uiso 0.59(2) 1 calc PR A 1
C20A C 0.882(2) 0.3349(11) 0.213(2) 0.146(13) Uani 0.41(2) 1 d PD A 2
H20C H 0.8640 0.3675 0.1718 0.176 Uiso 0.41(2) 1 calc PR A 2
H20D H 0.9348 0.3291 0.1980 0.176 Uiso 0.41(2) 1 calc PR A 2
C21A C 0.839(2) 0.2814(14) 0.1880(13) 0.174(13) Uani 0.41(2) 1 d PDU A 2
H21C H 0.7856 0.2872 0.1986 0.209 Uiso 0.41(2) 1 calc PR A 2
H21D H 0.8557 0.2484 0.2298 0.209 Uiso 0.41(2) 1 calc PR A 2
C22 C 0.8575(5) 0.2729(4) 0.0731(8) 0.168(4) Uani 1 1 d D . .
H221 H 0.8458 0.2872 0.0043 0.253 Uiso 0.59(2) 1 calc PR A 1
H222 H 0.8247 0.2411 0.0903 0.253 Uiso 0.59(2) 1 calc PR A 1
H223 H 0.9086 0.2596 0.0746 0.253 Uiso 0.59(2) 1 calc PR A 1
H224 H 0.8284 0.2415 0.0441 0.253 Uiso 0.41(2) 1 d PR A 2
H225 H 0.9097 0.2625 0.0721 0.253 Uiso 0.41(2) 1 d PR A 2
H226 H 0.8500 0.3077 0.0322 0.253 Uiso 0.41(2) 1 d PR A 2
C7 C 0.6475(4) 0.6788(3) 0.5657(5) 0.098(2) Uani 1 1 d . . .
H7A H 0.6390 0.6976 0.4994 0.147 Uiso 1 1 calc R . .
H7B H 0.6800 0.6457 0.5560 0.147 Uiso 1 1 calc R . .
H7C H 0.6706 0.7061 0.6131 0.147 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0686(9) 0.0580(8) 0.0476(8) -0.0023(8) -0.0016(8) -0.0017(9)
B1 0.068(6) 0.110(8) 0.068(5) -0.012(6) 0.007(5) -0.040(5)
C14 0.108(6) 0.083(5) 0.075(5) -0.015(4) 0.006(4) 0.012(4)
C16 0.128(6) 0.084(5) 0.085(5) -0.012(4) 0.010(5) 0.016(5)
F4 0.161(4) 0.234(6) 0.105(4) -0.008(4) 0.018(3) -0.094(4)
C10 0.092(5) 0.105(5) 0.070(5) -0.031(4) -0.013(4) 0.025(5)
C13 0.087(5) 0.070(4) 0.058(4) -0.016(3) -0.005(3) 0.007(3)
C1 0.104(6) 0.100(5) 0.085(6) -0.010(4) 0.005(4) -0.035(5)
C12 0.127(6) 0.138(7) 0.059(4) -0.020(5) -0.029(4) 0.026(6)
C4 0.070(5) 0.158(7) 0.129(7) -0.010(6) 0.007(5) -0.019(5)
C15 0.101(5) 0.075(4) 0.079(5) -0.010(4) 0.011(4) 0.017(4)
C3 0.170(8) 0.122(7) 0.110(7) 0.046(6) 0.035(6) -0.026(6)
C2 0.138(7) 0.098(6) 0.113(6) -0.026(5) 0.000(5) -0.051(5)
F3 0.339(10) 0.263(8) 0.157(6) 0.032(6) 0.107(7) 0.092(8)
C5 0.104(6) 0.085(5) 0.079(5) 0.020(4) 0.017(4) 0.024(4)
C9 0.099(5) 0.115(6) 0.076(5) -0.035(4) -0.004(4) 0.013(5)
F2 0.110(4) 0.213(7) 0.313(9) 0.101(7) -0.003(5) 0.010(4)
C8 0.119(6) 0.093(5) 0.118(6) 0.031(5) 0.020(5) 0.042(5)
C17 0.131(7) 0.092(6) 0.110(6) -0.010(5) 0.030(5) 0.024(5)
F1 0.228(7) 0.265(8) 0.218(7) 0.051(6) -0.049(6) -0.148(6)
C6 0.128(7) 0.164(8) 0.056(4) 0.002(5) -0.025(4) 0.034(6)
C18 0.154(8) 0.147(8) 0.130(8) -0.042(6) 0.001(7) 0.061(7)
C19 0.181(11) 0.166(10) 0.165(11) -0.024(9) 0.034(9) 0.044(8)
C11 0.090(5) 0.103(6) 0.187(9) -0.057(6) -0.006(6) -0.032(5)
C20 0.22(3) 0.14(2) 0.097(15) -0.020(15) -0.008(17) 0.077(19)
C21 0.202(19) 0.136(19) 0.137(19) -0.049(16) -0.018(17) -0.023(19)
C20A 0.23(3) 0.13(2) 0.07(3) -0.025(19) 0.01(2) 0.02(3)
C21A 0.22(2) 0.18(3) 0.13(3) -0.01(2) -0.04(2) -0.04(3)
C22 0.136(8) 0.208(12) 0.161(10) -0.080(9) 0.024(7) 0.006(7)
C7 0.106(6) 0.086(5) 0.101(6) 0.029(4) 0.029(5) 0.000(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
P1 C13 1.808(6) . ?
P1 C10 1.863(6) . ?
P1 C5 1.855(6) . ?
P1 C1 1.890(7) . ?
B1 F2 1.230(10) . ?
B1 F1 1.305(9) . ?
B1 F4 1.313(9) . ?
B1 F3 1.329(10) . ?
C14 C15 1.493(8) . ?
C14 C13 1.535(7) . ?
C16 C17 1.479(8) . ?
C16 C15 1.512(8) . ?
C10 C12 1.530(8) . ?
C10 C9 1.535(8) . ?
C10 C11 1.609(9) . ?
C1 C2 1.528(8) . ?
C1 C4 1.555(9) . ?
C1 C3 1.576(9) . ?
C5 C7 1.547(8) . ?
C5 C8 1.555(8) . ?
C5 C6 1.601(9) . ?
C17 C18 1.572(10) . ?
C18 C19 1.374(10) . ?
C19 C20 1.513(10) . ?
C19 C20A 1.65(3) . ?
C20 C21 1.472(10) . ?
C21 C22 1.517(9) . ?
C20A C21A 1.479(10) . ?
C21A C22 1.514(10) . ?

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
C13 P1 C10 103.7(3) . . ?
C13 P1 C5 109.2(3) . . ?
C10 P1 C5 112.9(3) . . ?
C13 P1 C1 107.3(3) . . ?
C10 P1 C1 110.6(3) . . ?
C5 P1 C1 112.5(3) . . ?
F2 B1 F1 113.3(9) . . ?
F2 B1 F4 117.8(9) . . ?
F1 B1 F4 109.8(8) . . ?
F2 B1 F3 107.3(9) . . ?
F1 B1 F3 101.6(9) . . ?
F4 B1 F3 105.5(8) . . ?
C15 C14 C13 111.5(5) . . ?
C17 C16 C15 115.2(6) . . ?
C12 C10 C9 109.4(6) . . ?
C12 C10 C11 106.6(6) . . ?
C9 C10 C11 108.0(6) . . ?
C12 C10 P1 111.5(5) . . ?
C9 C10 P1 113.0(5) . . ?
C11 C10 P1 108.2(5) . . ?
C14 C13 P1 122.7(4) . . ?
C2 C1 C4 108.2(6) . . ?
C2 C1 C3 106.6(6) . . ?
C4 C1 C3 109.7(6) . . ?
C2 C1 P1 111.2(5) . . ?
C4 C1 P1 111.5(5) . . ?
C3 C1 P1 109.4(5) . . ?
C14 C15 C16 112.8(6) . . ?
C7 C5 C8 108.1(6) . . ?
C7 C5 C6 107.4(6) . . ?
C8 C5 C6 109.6(6) . . ?
C7 C5 P1 110.8(5) . . ?
C8 C5 P1 111.5(5) . . ?
C6 C5 P1 109.3(5) . . ?
C16 C17 C18 112.2(7) . . ?
C19 C18 C17 115.7(8) . . ?
C18 C19 C20 118.8(13) . . ?
C18 C19 C20A 113.3(17) . . ?
C20 C19 C20A 36.6(10) . . ?
C21 C20 C19 113.4(12) . . ?
C20 C21 C22 109.8(12) . . ?
C21A C20A C19 108.0(17) . . ?
C20A C21A C22 101.8(15) . . ?
C21A C22 C21 40.1(12) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.048