# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010


data_global

_journal_coden_Cambridge         222

loop_
_publ_author_name
'Albrecht, Markus'
'Muller, Michael'
'Sackmann, Johannes'
'Hoffmann, Andreas'
'Dierkes, Fiete'
'Rissanen, Kari'
'Valkonen, Arto'

_publ_contact_author_name        'Albrecht, Markus'
_publ_contact_author_email       markus.albrecht@oc.rwth-aachen.de

_publ_section_title              
;
CH-Anion versus Anion-\/D Interactions in the Crystal and in
Solution of Pentafluorobenzyl Phosphonium Salts
;

# Attachment 'ah21.cif'

data_ah21
_database_code_depnum_ccdc_archive 'CCDC 795076'
#TrackingRef 'ah21.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H13 F5 P), H2 O, 2(Br)'
_chemical_formula_sum            'C30 H28 Br2 F10 O P2'
_chemical_formula_weight         816.28

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.8147(4)
_cell_length_b                   12.0612(3)
_cell_length_c                   14.5634(5)
_cell_angle_alpha                94.048(2)
_cell_angle_beta                 110.887(2)
_cell_angle_gamma                118.155(2)
_cell_volume                     1636.05(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6686
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    2.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6609
_exptl_absorpt_correction_T_max  0.8569
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19069
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5722
_reflns_number_gt                4115
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2006)'
_computing_publication_material  SHELXL-97

_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^ > 2\s(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^)+(0.0000P)^2^+3.0006P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5722
_refine_ls_number_parameters     415
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.30218(5) 0.01491(5) 0.25926(4) 0.03072(14) Uani 1 1 d D . .
P1 P 0.77614(12) 0.05416(11) 0.48040(9) 0.0229(3) Uani 1 1 d . . .
F1 F 0.8738(3) 0.2489(3) 0.3034(2) 0.0391(7) Uani 1 1 d . . .
F2 F 0.6930(3) 0.2771(3) 0.1462(2) 0.0483(8) Uani 1 1 d . . .
F3 F 0.4159(3) 0.0745(3) 0.0336(2) 0.0517(8) Uani 1 1 d . . .
F4 F 0.3295(3) -0.1618(3) 0.0719(2) 0.0454(8) Uani 1 1 d . . .
F5 F 0.5118(3) -0.1908(2) 0.22993(19) 0.0352(7) Uani 1 1 d . . .
C2 C 0.8029(5) 0.2135(4) 0.5052(3) 0.0213(10) Uani 1 1 d . . .
C3 C 0.6946(5) 0.2355(5) 0.4530(3) 0.0282(11) Uani 1 1 d . . .
H3 H 0.6030 0.1643 0.4042 0.034 Uiso 1 1 calc R . .
C4 C 0.7208(5) 0.3609(5) 0.4726(4) 0.0311(12) Uani 1 1 d . . .
H4 H 0.6472 0.3758 0.4363 0.037 Uiso 1 1 calc R . .
C5 C 0.8522(6) 0.4647(5) 0.5440(4) 0.0326(12) Uani 1 1 d . . .
H5 H 0.8688 0.5506 0.5572 0.039 Uiso 1 1 calc R . .
C6 C 0.9602(5) 0.4437(5) 0.5964(4) 0.0331(12) Uani 1 1 d . . .
H6 H 1.0507 0.5150 0.6465 0.040 Uiso 1 1 calc R . .
C7 C 0.9363(5) 0.3192(4) 0.5759(3) 0.0274(11) Uani 1 1 d . . .
H7 H 1.0117 0.3055 0.6104 0.033 Uiso 1 1 calc R . .
C8 C 0.7952(5) 0.0175(4) 0.3655(3) 0.0271(11) Uani 1 1 d . . .
H8A H 0.8955 0.0782 0.3782 0.032 Uiso 1 1 calc R . .
H8B H 0.7749 -0.0731 0.3510 0.032 Uiso 1 1 calc R . .
C9 C 0.6965(5) 0.0298(4) 0.2731(3) 0.0254(11) Uani 1 1 d . . .
C10 C 0.7377(5) 0.1464(4) 0.2474(4) 0.0287(11) Uani 1 1 d . . .
C11 C 0.6456(6) 0.1611(5) 0.1669(4) 0.0351(13) Uani 1 1 d . . .
C12 C 0.5078(6) 0.0586(5) 0.1095(4) 0.0370(13) Uani 1 1 d . . .
C13 C 0.4627(6) -0.0608(5) 0.1301(4) 0.0341(12) Uani 1 1 d . . .
C14 C 0.5579(5) -0.0730(4) 0.2112(4) 0.0279(11) Uani 1 1 d . . .
C15 C 0.6008(5) -0.0682(4) 0.4607(3) 0.0279(11) Uani 1 1 d . . .
H15A H 0.5881 -0.1551 0.4473 0.042 Uiso 1 1 calc R . .
H15B H 0.5294 -0.0657 0.4018 0.042 Uiso 1 1 calc R . .
H15C H 0.5886 -0.0511 0.5222 0.042 Uiso 1 1 calc R . .
C16 C 0.9073(5) 0.0472(4) 0.5843(4) 0.0298(11) Uani 1 1 d . . .
H16A H 0.8917 -0.0407 0.5698 0.045 Uiso 1 1 calc R . .
H16B H 0.8995 0.0663 0.6475 0.045 Uiso 1 1 calc R . .
H16C H 1.0031 0.1124 0.5927 0.045 Uiso 1 1 calc R . .
Br2 Br 0.74783(5) 0.70752(5) 0.43675(4) 0.03102(14) Uani 1 1 d . . .
P1A P 0.22922(13) 0.32383(12) 0.24236(9) 0.0271(3) Uani 1 1 d . . .
F1A F 0.2429(3) 0.4653(3) 0.0321(2) 0.0448(8) Uani 1 1 d . . .
F2A F 0.4653(4) 0.6816(3) 0.0324(2) 0.0552(9) Uani 1 1 d . . .
F3A F 0.7350(4) 0.7327(3) 0.1319(2) 0.0613(9) Uani 1 1 d . . .
F4A F 0.7793(3) 0.5627(3) 0.2281(2) 0.0496(8) Uani 1 1 d . . .
F5A F 0.5584(3) 0.3532(3) 0.2377(2) 0.0388(7) Uani 1 1 d . . .
C2A C 0.1705(5) 0.4350(4) 0.2174(3) 0.0248(10) Uani 1 1 d . . .
C3A C 0.0306(5) 0.3861(5) 0.1439(4) 0.0317(11) Uani 1 1 d . . .
H3A H -0.0331 0.2944 0.1107 0.038 Uiso 1 1 calc R . .
C4A C -0.0147(6) 0.4710(5) 0.1197(4) 0.0379(13) Uani 1 1 d . . .
H4A H -0.1097 0.4378 0.0696 0.045 Uiso 1 1 calc R . .
C5A C 0.0773(6) 0.6038(5) 0.1677(4) 0.0384(13) Uani 1 1 d . . .
H5A H 0.0452 0.6618 0.1507 0.046 Uiso 1 1 calc R . .
C6A C 0.2157(6) 0.6537(5) 0.2403(4) 0.0390(13) Uani 1 1 d . . .
H6A H 0.2786 0.7457 0.2725 0.047 Uiso 1 1 calc R . .
C7A C 0.2631(5) 0.5693(5) 0.2663(4) 0.0313(12) Uani 1 1 d . . .
H7A H 0.3579 0.6030 0.3170 0.038 Uiso 1 1 calc R . .
C8A C 0.2713(5) 0.2854(5) 0.1413(4) 0.0297(11) Uani 1 1 d . . .
H8A1 H 0.2952 0.2175 0.1520 0.036 Uiso 1 1 calc R . .
H8A2 H 0.1859 0.2486 0.0744 0.036 Uiso 1 1 calc R . .
C9A C 0.3956(5) 0.4048(4) 0.1381(3) 0.0253(11) Uani 1 1 d . . .
C10A C 0.3764(5) 0.4919(5) 0.0855(3) 0.0305(12) Uani 1 1 d . . .
C11A C 0.4881(6) 0.6000(5) 0.0838(4) 0.0365(13) Uani 1 1 d . . .
C12A C 0.6246(6) 0.6253(5) 0.1337(4) 0.0377(13) Uani 1 1 d . . .
C13A C 0.6477(5) 0.5413(5) 0.1834(3) 0.0337(12) Uani 1 1 d . . .
C14A C 0.5340(5) 0.4333(5) 0.1862(3) 0.0272(11) Uani 1 1 d . . .
C15A C 0.0906(5) 0.1748(5) 0.2442(4) 0.0392(13) Uani 1 1 d . . .
H15D H 0.1238 0.1143 0.2579 0.059 Uiso 1 1 calc R . .
H15E H 0.0061 0.1344 0.1775 0.059 Uiso 1 1 calc R . .
H15F H 0.0657 0.1937 0.2982 0.059 Uiso 1 1 calc R . .
C16A C 0.3826(5) 0.3907(5) 0.3622(4) 0.0356(12) Uani 1 1 d . . .
H16D H 0.4117 0.3271 0.3734 0.053 Uiso 1 1 calc R . .
H16E H 0.3598 0.4103 0.4174 0.053 Uiso 1 1 calc R . .
H16F H 0.4610 0.4718 0.3621 0.053 Uiso 1 1 calc R . .
O1 O 0.0724(6) -0.0725(5) 0.0137(4) 0.0972(18) Uani 1 1 d D . .
H1A H 0.119(6) -0.068(6) 0.076(2) 0.146 Uiso 1 1 d D . .
H1B H 0.023(12) -0.039(11) 0.019(8) 0.146 Uiso 0.50 1 d PD . .
H1C H 0.131(8) -0.023(10) -0.007(8) 0.146 Uiso 0.50 1 d PD . .

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
Br1 0.0324(3) 0.0328(3) 0.0325(3) 0.0098(2) 0.0150(2) 0.0208(2)
P1 0.0210(7) 0.0213(7) 0.0279(6) 0.0069(5) 0.0125(5) 0.0112(6)
F1 0.0431(19) 0.0282(16) 0.0582(19) 0.0172(14) 0.0338(16) 0.0188(15)
F2 0.076(2) 0.0468(19) 0.065(2) 0.0403(17) 0.0529(19) 0.0443(18)
F3 0.072(2) 0.071(2) 0.0373(17) 0.0271(16) 0.0266(17) 0.053(2)
F4 0.0425(19) 0.0453(19) 0.0313(16) -0.0008(14) 0.0093(15) 0.0180(17)
F5 0.0457(18) 0.0203(15) 0.0341(15) 0.0067(12) 0.0203(14) 0.0120(14)
C2 0.021(3) 0.024(3) 0.024(2) 0.008(2) 0.012(2) 0.014(2)
C3 0.022(3) 0.035(3) 0.028(3) 0.006(2) 0.012(2) 0.016(2)
C4 0.041(3) 0.047(3) 0.032(3) 0.018(3) 0.020(3) 0.037(3)
C5 0.046(3) 0.027(3) 0.038(3) 0.014(2) 0.024(3) 0.024(3)
C6 0.033(3) 0.025(3) 0.039(3) 0.008(2) 0.012(2) 0.017(3)
C7 0.027(3) 0.029(3) 0.031(3) 0.012(2) 0.011(2) 0.019(2)
C8 0.029(3) 0.024(3) 0.040(3) 0.012(2) 0.022(2) 0.017(2)
C9 0.040(3) 0.027(3) 0.029(3) 0.014(2) 0.026(2) 0.024(3)
C10 0.035(3) 0.021(3) 0.039(3) 0.009(2) 0.024(3) 0.016(3)
C11 0.062(4) 0.042(3) 0.037(3) 0.022(3) 0.038(3) 0.039(3)
C12 0.053(4) 0.049(4) 0.030(3) 0.017(3) 0.022(3) 0.038(3)
C13 0.041(3) 0.035(3) 0.032(3) 0.005(2) 0.020(3) 0.023(3)
C14 0.040(3) 0.021(3) 0.031(3) 0.009(2) 0.023(3) 0.017(3)
C15 0.027(3) 0.025(3) 0.027(2) 0.004(2) 0.013(2) 0.010(2)
C16 0.032(3) 0.025(3) 0.039(3) 0.016(2) 0.017(2) 0.018(2)
Br2 0.0392(3) 0.0249(3) 0.0395(3) 0.0133(2) 0.0238(2) 0.0195(2)
P1A 0.0237(7) 0.0320(7) 0.0325(7) 0.0135(6) 0.0142(6) 0.0181(6)
F1A 0.053(2) 0.071(2) 0.0360(16) 0.0250(15) 0.0198(15) 0.0496(19)
F2A 0.108(3) 0.052(2) 0.0489(19) 0.0360(16) 0.051(2) 0.059(2)
F3A 0.071(2) 0.0388(19) 0.059(2) 0.0119(16) 0.039(2) 0.0120(18)
F4A 0.0298(18) 0.068(2) 0.0386(17) 0.0048(15) 0.0110(14) 0.0216(17)
F5A 0.0432(18) 0.060(2) 0.0395(16) 0.0267(15) 0.0229(15) 0.0408(17)
C2A 0.027(3) 0.029(3) 0.027(2) 0.010(2) 0.016(2) 0.017(2)
C3A 0.026(3) 0.030(3) 0.038(3) 0.012(2) 0.012(2) 0.015(2)
C4A 0.031(3) 0.038(3) 0.049(3) 0.023(3) 0.018(3) 0.020(3)
C5A 0.045(4) 0.041(3) 0.049(3) 0.023(3) 0.028(3) 0.031(3)
C6A 0.040(3) 0.023(3) 0.054(3) 0.011(3) 0.024(3) 0.014(3)
C7A 0.029(3) 0.035(3) 0.032(3) 0.010(2) 0.014(2) 0.017(3)
C8A 0.034(3) 0.033(3) 0.033(3) 0.010(2) 0.015(2) 0.025(3)
C9A 0.032(3) 0.030(3) 0.025(2) 0.011(2) 0.016(2) 0.022(2)
C10A 0.035(3) 0.052(3) 0.019(2) 0.011(2) 0.013(2) 0.033(3)
C11A 0.064(4) 0.035(3) 0.028(3) 0.015(2) 0.029(3) 0.032(3)
C12A 0.048(4) 0.029(3) 0.029(3) 0.003(2) 0.023(3) 0.012(3)
C13A 0.032(3) 0.045(3) 0.020(2) 0.006(2) 0.011(2) 0.019(3)
C14A 0.033(3) 0.036(3) 0.022(2) 0.011(2) 0.011(2) 0.026(3)
C15A 0.037(3) 0.031(3) 0.065(4) 0.024(3) 0.028(3) 0.023(3)
C16A 0.035(3) 0.051(3) 0.032(3) 0.018(3) 0.018(2) 0.028(3)
O1 0.103(4) 0.092(4) 0.062(3) -0.012(3) -0.019(3) 0.072(4)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C16 1.779(4) . ?
P1 C2 1.781(4) . ?
P1 C15 1.784(4) . ?
P1 C8 1.818(4) . ?
F1 C10 1.351(5) . ?
F2 C11 1.342(5) . ?
F3 C12 1.345(5) . ?
F4 C13 1.331(6) . ?
F5 C14 1.350(5) . ?
C2 C7 1.389(6) . ?
C2 C3 1.393(6) . ?
C3 C4 1.378(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.506(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.380(7) . ?
C9 C10 1.383(6) . ?
C10 C11 1.375(7) . ?
C11 C12 1.365(7) . ?
C12 C13 1.378(7) . ?
C13 C14 1.384(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
P1A C16A 1.774(5) . ?
P1A C15A 1.782(5) . ?
P1A C2A 1.783(4) . ?
P1A C8A 1.809(4) . ?
F1A C10A 1.345(5) . ?
F2A C11A 1.346(5) . ?
F3A C12A 1.348(6) . ?
F4A C13A 1.336(5) . ?
F5A C14A 1.339(5) . ?
C2A C7A 1.391(6) . ?
C2A C3A 1.398(6) . ?
C3A C4A 1.376(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.376(7) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.379(7) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.391(6) . ?
C6A H6A 0.9500 . ?
C7A H7A 0.9500 . ?
C8A C9A 1.514(6) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C14A 1.379(6) . ?
C9A C10A 1.399(6) . ?
C10A C11A 1.359(7) . ?
C11A C12A 1.375(7) . ?
C12A C13A 1.359(7) . ?
C13A C14A 1.378(7) . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
O1 H1A 0.86(2) . ?
O1 H1B 0.87(2) . ?
O1 H1C 0.84(2) . ?

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
C16 P1 C2 110.1(2) . . ?
C16 P1 C15 110.1(2) . . ?
C2 P1 C15 110.7(2) . . ?
C16 P1 C8 107.5(2) . . ?
C2 P1 C8 110.3(2) . . ?
C15 P1 C8 108.1(2) . . ?
C7 C2 C3 119.2(4) . . ?
C7 C2 P1 119.3(3) . . ?
C3 C2 P1 121.5(3) . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 119.9(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.5(4) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C9 C8 P1 112.6(3) . . ?
C9 C8 H8A 109.1 . . ?
P1 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
P1 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C14 C9 C10 116.0(4) . . ?
C14 C9 C8 122.0(4) . . ?
C10 C9 C8 121.9(4) . . ?
F1 C10 C11 119.2(4) . . ?
F1 C10 C9 118.4(4) . . ?
C11 C10 C9 122.4(5) . . ?
F2 C11 C12 120.8(5) . . ?
F2 C11 C10 119.2(5) . . ?
C12 C11 C10 120.0(5) . . ?
F3 C12 C11 120.0(5) . . ?
F3 C12 C13 120.1(5) . . ?
C11 C12 C13 119.9(5) . . ?
F4 C13 C12 119.7(5) . . ?
F4 C13 C14 121.4(4) . . ?
C12 C13 C14 118.9(5) . . ?
F5 C14 C9 119.2(4) . . ?
F5 C14 C13 118.0(4) . . ?
C9 C14 C13 122.8(4) . . ?
P1 C15 H15A 109.5 . . ?
P1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
P1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
P1 C16 H16A 109.5 . . ?
P1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
P1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C16A P1A C15A 108.2(2) . . ?
C16A P1A C2A 111.7(2) . . ?
C15A P1A C2A 110.1(2) . . ?
C16A P1A C8A 109.2(2) . . ?
C15A P1A C8A 108.2(2) . . ?
C2A P1A C8A 109.4(2) . . ?
C7A C2A C3A 119.9(4) . . ?
C7A C2A P1A 121.1(3) . . ?
C3A C2A P1A 118.9(3) . . ?
C4A C3A C2A 119.9(5) . . ?
C4A C3A H3A 120.1 . . ?
C2A C3A H3A 120.1 . . ?
C3A C4A C5A 120.1(5) . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A H4A 119.9 . . ?
C4A C5A C6A 120.7(5) . . ?
C4A C5A H5A 119.6 . . ?
C6A C5A H5A 119.6 . . ?
C5A C6A C7A 120.0(5) . . ?
C5A C6A H6A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C6A C7A C2A 119.4(4) . . ?
C6A C7A H7A 120.3 . . ?
C2A C7A H7A 120.3 . . ?
C9A C8A P1A 112.3(3) . . ?
C9A C8A H8A1 109.1 . . ?
P1A C8A H8A1 109.1 . . ?
C9A C8A H8A2 109.1 . . ?
P1A C8A H8A2 109.1 . . ?
H8A1 C8A H8A2 107.9 . . ?
C14A C9A C10A 116.1(4) . . ?
C14A C9A C8A 121.9(4) . . ?
C10A C9A C8A 121.9(4) . . ?
F1A C10A C11A 119.1(4) . . ?
F1A C10A C9A 118.9(4) . . ?
C11A C10A C9A 122.0(4) . . ?
F2A C11A C10A 120.2(5) . . ?
F2A C11A C12A 119.9(5) . . ?
C10A C11A C12A 119.9(4) . . ?
F3A C12A C13A 120.2(5) . . ?
F3A C12A C11A 119.6(5) . . ?
C13A C12A C11A 120.2(5) . . ?
F4A C13A C12A 120.2(5) . . ?
F4A C13A C14A 120.4(4) . . ?
C12A C13A C14A 119.4(5) . . ?
F5A C14A C13A 118.9(4) . . ?
F5A C14A C9A 118.6(4) . . ?
C13A C14A C9A 122.4(4) . . ?
P1A C15A H15D 109.5 . . ?
P1A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
P1A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
P1A C16A H16D 109.5 . . ?
P1A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
P1A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
H1A O1 H1B 104(5) . . ?
H1A O1 H1C 109(5) . . ?
H1B O1 H1C 108(5) . . ?

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
C16 P1 C2 C7 21.0(4) . . . . ?
C15 P1 C2 C7 143.0(4) . . . . ?
C8 P1 C2 C7 -97.5(4) . . . . ?
C16 P1 C2 C3 -161.1(4) . . . . ?
C15 P1 C2 C3 -39.1(4) . . . . ?
C8 P1 C2 C3 80.5(4) . . . . ?
C7 C2 C3 C4 -0.4(6) . . . . ?
P1 C2 C3 C4 -178.3(3) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C4 C5 C6 C7 0.9(7) . . . . ?
C5 C6 C7 C2 -2.1(7) . . . . ?
C3 C2 C7 C6 1.8(7) . . . . ?
P1 C2 C7 C6 179.8(4) . . . . ?
C16 P1 C8 C9 -175.9(3) . . . . ?
C2 P1 C8 C9 -55.8(4) . . . . ?
C15 P1 C8 C9 65.3(4) . . . . ?
P1 C8 C9 C14 -86.7(5) . . . . ?
P1 C8 C9 C10 90.8(4) . . . . ?
C14 C9 C10 F1 -177.7(4) . . . . ?
C8 C9 C10 F1 4.6(6) . . . . ?
C14 C9 C10 C11 1.7(6) . . . . ?
C8 C9 C10 C11 -175.9(4) . . . . ?
F1 C10 C11 F2 -0.4(6) . . . . ?
C9 C10 C11 F2 -179.8(4) . . . . ?
F1 C10 C11 C12 180.0(4) . . . . ?
C9 C10 C11 C12 0.5(7) . . . . ?
F2 C11 C12 F3 -2.5(7) . . . . ?
C10 C11 C12 F3 177.2(4) . . . . ?
F2 C11 C12 C13 177.9(4) . . . . ?
C10 C11 C12 C13 -2.4(7) . . . . ?
F3 C12 C13 F4 2.6(6) . . . . ?
C11 C12 C13 F4 -177.9(4) . . . . ?
F3 C12 C13 C14 -177.6(4) . . . . ?
C11 C12 C13 C14 2.0(7) . . . . ?
C10 C9 C14 F5 178.1(4) . . . . ?
C8 C9 C14 F5 -4.2(6) . . . . ?
C10 C9 C14 C13 -2.2(6) . . . . ?
C8 C9 C14 C13 175.5(4) . . . . ?
F4 C13 C14 F5 -0.1(6) . . . . ?
C12 C13 C14 F5 -179.9(4) . . . . ?
F4 C13 C14 C9 -179.8(4) . . . . ?
C12 C13 C14 C9 0.4(7) . . . . ?
C16A P1A C2A C7A 21.8(4) . . . . ?
C15A P1A C2A C7A 142.0(4) . . . . ?
C8A P1A C2A C7A -99.2(4) . . . . ?
C16A P1A C2A C3A -161.1(3) . . . . ?
C15A P1A C2A C3A -40.8(4) . . . . ?
C8A P1A C2A C3A 78.0(4) . . . . ?
C7A C2A C3A C4A 0.5(7) . . . . ?
P1A C2A C3A C4A -176.7(4) . . . . ?
C2A C3A C4A C5A -0.1(7) . . . . ?
C3A C4A C5A C6A 0.2(8) . . . . ?
C4A C5A C6A C7A -0.6(7) . . . . ?
C5A C6A C7A C2A 0.9(7) . . . . ?
C3A C2A C7A C6A -0.9(7) . . . . ?
P1A C2A C7A C6A 176.3(3) . . . . ?
C16A P1A C8A C9A -58.5(4) . . . . ?
C15A P1A C8A C9A -176.1(3) . . . . ?
C2A P1A C8A C9A 64.0(4) . . . . ?
P1A C8A C9A C14A 95.6(4) . . . . ?
P1A C8A C9A C10A -84.9(5) . . . . ?
C14A C9A C10A F1A 176.3(4) . . . . ?
C8A C9A C10A F1A -3.3(6) . . . . ?
C14A C9A C10A C11A -1.4(6) . . . . ?
C8A C9A C10A C11A 179.0(4) . . . . ?
F1A C10A C11A F2A 2.4(6) . . . . ?
C9A C10A C11A F2A -179.9(4) . . . . ?
F1A C10A C11A C12A -176.8(4) . . . . ?
C9A C10A C11A C12A 0.9(7) . . . . ?
F2A C11A C12A F3A 0.8(7) . . . . ?
C10A C11A C12A F3A -179.9(4) . . . . ?
F2A C11A C12A C13A -178.2(4) . . . . ?
C10A C11A C12A C13A 1.1(7) . . . . ?
F3A C12A C13A F4A -1.9(7) . . . . ?
C11A C12A C13A F4A 177.0(4) . . . . ?
F3A C12A C13A C14A 178.7(4) . . . . ?
C11A C12A C13A C14A -2.3(7) . . . . ?
F4A C13A C14A F5A 2.5(6) . . . . ?
C12A C13A C14A F5A -178.2(4) . . . . ?
F4A C13A C14A C9A -177.7(4) . . . . ?
C12A C13A C14A C9A 1.7(7) . . . . ?
C10A C9A C14A F5A -180.0(4) . . . . ?
C8A C9A C14A F5A -0.4(6) . . . . ?
C10A C9A C14A C13A 0.2(6) . . . . ?
C8A C9A C14A C13A 179.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A Br1 0.86(2) 2.50(2) 3.334(4) 163(6) .
O1 H1B O1 0.87(2) 2.11(2) 2.929(9) 157(6) 2

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.098

# Attachment 'mm-ah52.cif'

data_mm-ah52
_database_code_depnum_ccdc_archive 'CCDC 795077'
#TrackingRef 'mm-ah52.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 F5 P, I'
_chemical_formula_sum            'C15 H13 F5 I P'
_chemical_formula_weight         446.12

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   12.6682(3)
_cell_length_b                   18.0617(4)
_cell_length_c                   14.3740(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.972(2)
_cell_angle_gamma                90.00
_cell_volume                     3288.43(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8213
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    2.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_T_max  0.9028
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41227
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5799
_reflns_number_gt                4832
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2006)'
_computing_publication_material  SHELXL-97

_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^ > 2\s(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^)+(0.0000P)^2^+6.4643P] 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         5799
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0635
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_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
I1 I 0.89353(2) 0.613473(15) 0.685546(18) 0.02653(8) Uani 1 1 d . . .
P1 P 0.55748(8) 0.63018(5) 0.66621(7) 0.0204(2) Uani 1 1 d . . .
F9 F 0.68576(19) 0.47774(13) 0.79791(16) 0.0347(6) Uani 1 1 d . . .
F10 F 0.5956(3) 0.36093(14) 0.88151(18) 0.0488(8) Uani 1 1 d . . .
F11 F 0.4004(3) 0.37395(15) 0.95531(18) 0.0521(8) Uani 1 1 d . . .
F12 F 0.3014(2) 0.50636(17) 0.95254(17) 0.0462(7) Uani 1 1 d . . .
F13 F 0.3951(2) 0.62542(14) 0.87696(17) 0.0386(6) Uani 1 1 d . . .
C1 C 0.4182(3) 0.6415(2) 0.6572(3) 0.0211(8) Uani 1 1 d . . .
C2 C 0.3522(3) 0.5872(2) 0.6187(3) 0.0280(10) Uani 1 1 d . . .
H2 H 0.3815 0.5423 0.5961 0.034 Uiso 1 1 calc R . .
C3 C 0.2450(4) 0.5985(2) 0.6135(3) 0.0355(11) Uani 1 1 d . . .
H3 H 0.2004 0.5615 0.5871 0.043 Uiso 1 1 calc R . .
C4 C 0.2017(3) 0.6632(2) 0.6465(3) 0.0296(10) Uani 1 1 d . . .
H4 H 0.1276 0.6708 0.6427 0.036 Uiso 1 1 calc R . .
C5 C 0.2669(3) 0.7170(2) 0.6850(3) 0.0300(10) Uani 1 1 d . . .
H5 H 0.2370 0.7616 0.7078 0.036 Uiso 1 1 calc R . .
C6 C 0.3738(3) 0.7069(2) 0.6907(3) 0.0299(10) Uani 1 1 d . . .
H6 H 0.4178 0.7441 0.7174 0.036 Uiso 1 1 calc R . .
C7 C 0.5945(3) 0.6206(2) 0.7882(3) 0.0244(9) Uani 1 1 d . . .
H7A H 0.6721 0.6151 0.7938 0.029 Uiso 1 1 calc R . .
H7B H 0.5744 0.6662 0.8218 0.029 Uiso 1 1 calc R . .
C8 C 0.5423(3) 0.5550(2) 0.8328(3) 0.0209(9) Uani 1 1 d . . .
C9 C 0.5904(3) 0.4859(2) 0.8363(3) 0.0256(10) Uani 1 1 d . . .
C10 C 0.5443(4) 0.4257(2) 0.8775(3) 0.0324(11) Uani 1 1 d . . .
C11 C 0.4472(4) 0.4328(2) 0.9152(3) 0.0338(11) Uani 1 1 d . . .
C12 C 0.3954(3) 0.4993(3) 0.9135(3) 0.0298(10) Uani 1 1 d . . .
C13 C 0.4445(3) 0.5595(2) 0.8731(3) 0.0268(10) Uani 1 1 d . . .
C14 C 0.5992(3) 0.5507(2) 0.6041(3) 0.0242(9) Uani 1 1 d . . .
H14A H 0.6761 0.5457 0.6101 0.036 Uiso 1 1 calc R . .
H14B H 0.5794 0.5560 0.5382 0.036 Uiso 1 1 calc R . .
H14C H 0.5653 0.5065 0.6296 0.036 Uiso 1 1 calc R . .
C15 C 0.6223(3) 0.7101(2) 0.6236(3) 0.0270(9) Uani 1 1 d . . .
H15A H 0.6989 0.7032 0.6288 0.040 Uiso 1 1 calc R . .
H15B H 0.6017 0.7533 0.6603 0.040 Uiso 1 1 calc R . .
H15C H 0.6021 0.7179 0.5582 0.040 Uiso 1 1 calc R . .
I1A I 0.42851(2) 0.352688(15) 0.652710(18) 0.02615(8) Uani 1 1 d . . .
P1A P 1.08653(9) 0.32958(6) 0.62965(7) 0.0236(2) Uani 1 1 d . . .
F9A F 1.21047(19) 0.47458(13) 0.77181(16) 0.0329(6) Uani 1 1 d . . .
F10A F 1.1093(2) 0.58557(13) 0.85785(18) 0.0490(8) Uani 1 1 d . . .
F11A F 0.9171(3) 0.56163(16) 0.93408(18) 0.0552(9) Uani 1 1 d . . .
F12A F 0.8341(2) 0.42280(17) 0.93305(18) 0.0517(8) Uani 1 1 d . . .
F13A F 0.9362(2) 0.31150(14) 0.84883(17) 0.0384(6) Uani 1 1 d . . .
C1A C 0.9477(3) 0.3171(2) 0.6156(3) 0.0235(9) Uani 1 1 d . . .
C2A C 0.9066(3) 0.2495(2) 0.5855(3) 0.0270(10) Uani 1 1 d . . .
H2A H 0.9530 0.2095 0.5732 0.032 Uiso 1 1 calc R . .
C3A C 0.7992(3) 0.2402(2) 0.5734(3) 0.0319(10) Uani 1 1 d . . .
H3A H 0.7720 0.1941 0.5521 0.038 Uiso 1 1 calc R . .
C4A C 0.7315(4) 0.2976(2) 0.5919(3) 0.0323(10) Uani 1 1 d . . .
H4A H 0.6575 0.2908 0.5841 0.039 Uiso 1 1 calc R . .
C5A C 0.7703(4) 0.3648(2) 0.6218(3) 0.0354(11) Uani 1 1 d . . .
H5A H 0.7228 0.4040 0.6347 0.042 Uiso 1 1 calc R . .
C6A C 0.8768(4) 0.3757(2) 0.6332(3) 0.0311(10) Uani 1 1 d . . .
H6A H 0.9029 0.4226 0.6529 0.037 Uiso 1 1 calc R . .
C7A C 1.1268(3) 0.3294(2) 0.7517(3) 0.0244(9) Uani 1 1 d . . .
H7C H 1.1088 0.2810 0.7796 0.029 Uiso 1 1 calc R . .
H7D H 1.2044 0.3356 0.7566 0.029 Uiso 1 1 calc R . .
C8A C 1.0744(3) 0.3900(2) 0.8052(3) 0.0236(9) Uani 1 1 d . . .
C9A C 1.1170(3) 0.4609(2) 0.8109(3) 0.0254(9) Uani 1 1 d . . .
C10A C 1.0652(4) 0.5183(2) 0.8540(3) 0.0337(11) Uani 1 1 d . . .
C11A C 0.9690(4) 0.5055(3) 0.8930(3) 0.0349(11) Uani 1 1 d . . .
C12A C 0.9262(4) 0.4362(3) 0.8912(3) 0.0369(12) Uani 1 1 d . . .
C13A C 0.9792(3) 0.3797(2) 0.8486(3) 0.0273(10) Uani 1 1 d . . .
C14A C 1.1235(4) 0.4165(2) 0.5809(3) 0.0320(10) Uani 1 1 d . . .
H14D H 1.1999 0.4234 0.5885 0.048 Uiso 1 1 calc R . .
H14E H 1.0865 0.4565 0.6129 0.048 Uiso 1 1 calc R . .
H14F H 1.1044 0.4173 0.5146 0.048 Uiso 1 1 calc R . .
C15A C 1.1564(3) 0.2566(2) 0.5750(3) 0.0330(10) Uani 1 1 d . . .
H15D H 1.2325 0.2644 0.5837 0.050 Uiso 1 1 calc R . .
H15E H 1.1387 0.2560 0.5084 0.050 Uiso 1 1 calc R . .
H15F H 1.1364 0.2092 0.6029 0.050 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
I1 0.02317(15) 0.03055(16) 0.02581(15) 0.00047(12) -0.00196(11) 0.00014(12)
P1 0.0225(6) 0.0182(5) 0.0204(5) 0.0004(4) -0.0012(4) 0.0016(4)
F9 0.0287(14) 0.0409(15) 0.0345(14) 0.0014(11) 0.0039(11) 0.0155(11)
F10 0.080(2) 0.0267(14) 0.0398(16) 0.0004(12) -0.0002(15) 0.0122(14)
F11 0.076(2) 0.0420(17) 0.0380(16) -0.0021(13) 0.0046(15) -0.0293(15)
F12 0.0301(15) 0.081(2) 0.0275(14) -0.0038(13) 0.0049(11) -0.0060(14)
F13 0.0385(16) 0.0453(16) 0.0324(14) 0.0009(12) 0.0059(12) 0.0196(12)
C1 0.024(2) 0.020(2) 0.020(2) 0.0004(16) -0.0016(16) 0.0001(17)
C2 0.031(2) 0.017(2) 0.035(2) 0.0017(18) -0.0019(19) 0.0007(18)
C3 0.033(3) 0.025(2) 0.049(3) 0.006(2) -0.005(2) -0.008(2)
C4 0.020(2) 0.037(3) 0.032(2) 0.010(2) -0.0012(18) -0.0004(19)
C5 0.025(2) 0.034(2) 0.032(2) -0.0033(19) -0.0023(19) 0.0082(19)
C6 0.031(3) 0.026(2) 0.032(2) -0.0067(19) -0.007(2) 0.0001(19)
C7 0.021(2) 0.028(2) 0.024(2) -0.0002(17) -0.0010(17) 0.0032(18)
C8 0.024(2) 0.023(2) 0.015(2) -0.0036(16) -0.0012(16) 0.0035(17)
C9 0.030(2) 0.032(2) 0.014(2) -0.0030(17) -0.0023(17) 0.0061(19)
C10 0.048(3) 0.024(2) 0.025(2) -0.0072(19) -0.004(2) 0.003(2)
C11 0.049(3) 0.030(3) 0.022(2) -0.0028(19) -0.004(2) -0.009(2)
C12 0.024(2) 0.050(3) 0.016(2) -0.0037(19) 0.0026(17) -0.007(2)
C13 0.028(2) 0.037(3) 0.015(2) -0.0078(18) -0.0038(17) 0.009(2)
C14 0.029(2) 0.025(2) 0.019(2) -0.0004(17) 0.0043(17) 0.0041(18)
C15 0.026(2) 0.022(2) 0.033(2) 0.0038(18) 0.0034(19) 0.0004(18)
I1A 0.02388(15) 0.02791(16) 0.02659(15) 0.00287(11) -0.00179(11) -0.00110(12)
P1A 0.0276(6) 0.0215(5) 0.0218(6) -0.0027(4) 0.0016(4) -0.0035(5)
F9A 0.0371(15) 0.0313(14) 0.0300(13) -0.0004(10) -0.0034(11) -0.0139(11)
F10A 0.081(2) 0.0223(14) 0.0429(16) -0.0087(12) -0.0219(15) 0.0013(14)
F11A 0.081(2) 0.0559(19) 0.0291(15) -0.0077(13) -0.0056(14) 0.0412(17)
F12A 0.0338(16) 0.089(2) 0.0322(15) 0.0079(14) 0.0085(12) 0.0194(15)
F13A 0.0359(15) 0.0409(16) 0.0385(15) 0.0043(12) 0.0029(12) -0.0139(12)
C1A 0.032(2) 0.024(2) 0.015(2) 0.0010(17) 0.0028(17) -0.0002(19)
C2A 0.030(2) 0.021(2) 0.031(2) -0.0005(18) 0.0046(19) 0.0016(18)
C3A 0.028(2) 0.030(2) 0.038(3) 0.002(2) 0.004(2) -0.004(2)
C4A 0.027(2) 0.041(3) 0.030(2) 0.003(2) 0.0029(19) 0.004(2)
C5A 0.036(3) 0.034(3) 0.036(3) -0.002(2) 0.002(2) 0.022(2)
C6A 0.040(3) 0.028(2) 0.025(2) -0.0035(18) -0.002(2) 0.006(2)
C7A 0.022(2) 0.025(2) 0.026(2) 0.0015(17) -0.0037(17) -0.0002(17)
C8A 0.029(2) 0.024(2) 0.018(2) -0.0037(17) -0.0084(17) 0.0001(18)
C9A 0.030(2) 0.028(2) 0.019(2) -0.0007(18) -0.0056(18) -0.0009(19)
C10A 0.056(3) 0.020(2) 0.024(2) -0.0007(18) -0.018(2) 0.002(2)
C11A 0.050(3) 0.035(3) 0.020(2) -0.0040(19) -0.008(2) 0.023(2)
C12A 0.034(3) 0.059(3) 0.018(2) 0.000(2) -0.002(2) 0.013(2)
C13A 0.029(2) 0.033(2) 0.020(2) 0.0014(18) -0.0036(18) -0.002(2)
C14A 0.042(3) 0.029(2) 0.025(2) 0.0039(19) 0.000(2) -0.012(2)
C15A 0.028(2) 0.033(3) 0.038(3) -0.011(2) 0.001(2) -0.004(2)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C15 1.775(4) . ?
P1 C14 1.776(4) . ?
P1 C1 1.779(4) . ?
P1 C7 1.816(4) . ?
F9 C9 1.344(5) . ?
F10 C10 1.338(5) . ?
F11 C11 1.351(5) . ?
F12 C12 1.331(5) . ?
F13 C13 1.346(5) . ?
C1 C2 1.397(6) . ?
C1 C6 1.397(6) . ?
C2 C3 1.375(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.368(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.506(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.380(6) . ?
C8 C9 1.389(6) . ?
C9 C10 1.373(6) . ?
C10 C11 1.359(7) . ?
C11 C12 1.369(6) . ?
C12 C13 1.384(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
P1A C15A 1.778(4) . ?
P1A C1A 1.781(4) . ?
P1A C14A 1.784(4) . ?
P1A C7A 1.819(4) . ?
F9A C9A 1.343(5) . ?
F10A C10A 1.338(5) . ?
F11A C11A 1.350(5) . ?
F12A C12A 1.344(5) . ?
F13A C13A 1.346(5) . ?
C1A C2A 1.393(6) . ?
C1A C6A 1.414(6) . ?
C2A C3A 1.379(6) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.374(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.376(6) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.370(6) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.499(6) . ?
C7A H7C 0.9900 . ?
C7A H7D 0.9900 . ?
C8A C13A 1.380(6) . ?
C8A C9A 1.392(6) . ?
C9A C10A 1.379(6) . ?
C10A C11A 1.369(7) . ?
C11A C12A 1.366(7) . ?
C12A C13A 1.371(6) . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?

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
C15 P1 C14 109.9(2) . . ?
C15 P1 C1 110.23(19) . . ?
C14 P1 C1 111.09(19) . . ?
C15 P1 C7 107.27(19) . . ?
C14 P1 C7 109.55(19) . . ?
C1 P1 C7 108.71(19) . . ?
C2 C1 C6 119.3(4) . . ?
C2 C1 P1 122.3(3) . . ?
C6 C1 P1 118.4(3) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 P1 112.2(3) . . ?
C8 C7 H7A 109.2 . . ?
P1 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
P1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C13 C8 C9 115.8(4) . . ?
C13 C8 C7 122.4(4) . . ?
C9 C8 C7 121.8(4) . . ?
F9 C9 C10 118.8(4) . . ?
F9 C9 C8 118.7(4) . . ?
C10 C9 C8 122.5(4) . . ?
F10 C10 C11 120.5(4) . . ?
F10 C10 C9 120.1(4) . . ?
C11 C10 C9 119.4(4) . . ?
F11 C11 C10 120.2(4) . . ?
F11 C11 C12 119.0(4) . . ?
C10 C11 C12 120.8(4) . . ?
F12 C12 C11 120.5(4) . . ?
F12 C12 C13 120.9(4) . . ?
C11 C12 C13 118.6(4) . . ?
F13 C13 C8 119.4(4) . . ?
F13 C13 C12 117.7(4) . . ?
C8 C13 C12 122.8(4) . . ?
P1 C14 H14A 109.5 . . ?
P1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
P1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P1 C15 H15A 109.5 . . ?
P1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
P1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C15A P1A C1A 110.74(19) . . ?
C15A P1A C14A 110.0(2) . . ?
C1A P1A C14A 109.4(2) . . ?
C15A P1A C7A 106.9(2) . . ?
C1A P1A C7A 111.68(19) . . ?
C14A P1A C7A 108.00(19) . . ?
C2A C1A C6A 118.5(4) . . ?
C2A C1A P1A 120.6(3) . . ?
C6A C1A P1A 120.9(3) . . ?
C3A C2A C1A 120.6(4) . . ?
C3A C2A H2A 119.7 . . ?
C1A C2A H2A 119.7 . . ?
C4A C3A C2A 120.1(4) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.3(4) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C6A C5A C4A 120.7(4) . . ?
C6A C5A H5A 119.7 . . ?
C4A C5A H5A 119.7 . . ?
C5A C6A C1A 119.9(4) . . ?
C5A C6A H6A 120.1 . . ?
C1A C6A H6A 120.1 . . ?
C8A C7A P1A 111.9(3) . . ?
C8A C7A H7C 109.2 . . ?
P1A C7A H7C 109.2 . . ?
C8A C7A H7D 109.2 . . ?
P1A C7A H7D 109.2 . . ?
H7C C7A H7D 107.9 . . ?
C13A C8A C9A 116.0(4) . . ?
C13A C8A C7A 122.2(4) . . ?
C9A C8A C7A 121.8(4) . . ?
F9A C9A C10A 118.6(4) . . ?
F9A C9A C8A 119.3(4) . . ?
C10A C9A C8A 122.1(4) . . ?
F10A C10A C11A 120.7(4) . . ?
F10A C10A C9A 120.0(5) . . ?
C11A C10A C9A 119.4(4) . . ?
F11A C11A C12A 120.0(5) . . ?
F11A C11A C10A 119.8(4) . . ?
C12A C11A C10A 120.2(4) . . ?
F12A C12A C11A 120.3(4) . . ?
F12A C12A C13A 120.1(4) . . ?
C11A C12A C13A 119.6(4) . . ?
F13A C13A C12A 118.6(4) . . ?
F13A C13A C8A 118.7(4) . . ?
C12A C13A C8A 122.7(4) . . ?
P1A C14A H14D 109.5 . . ?
P1A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
P1A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
P1A C15A H15D 109.5 . . ?
P1A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
P1A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?

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
C15 P1 C1 C2 131.6(3) . . . . ?
C14 P1 C1 C2 9.5(4) . . . . ?
C7 P1 C1 C2 -111.1(4) . . . . ?
C15 P1 C1 C6 -48.9(4) . . . . ?
C14 P1 C1 C6 -171.0(3) . . . . ?
C7 P1 C1 C6 68.4(4) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
P1 C1 C2 C3 179.9(3) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C2 C1 C6 C5 -0.3(6) . . . . ?
P1 C1 C6 C5 -179.8(3) . . . . ?
C15 P1 C7 C8 178.9(3) . . . . ?
C14 P1 C7 C8 -61.8(3) . . . . ?
C1 P1 C7 C8 59.7(3) . . . . ?
P1 C7 C8 C13 -88.4(4) . . . . ?
P1 C7 C8 C9 92.0(4) . . . . ?
C13 C8 C9 F9 179.8(3) . . . . ?
C7 C8 C9 F9 -0.6(5) . . . . ?
C13 C8 C9 C10 -0.3(6) . . . . ?
C7 C8 C9 C10 179.3(4) . . . . ?
F9 C9 C10 F10 2.0(6) . . . . ?
C8 C9 C10 F10 -177.8(4) . . . . ?
F9 C9 C10 C11 -178.9(4) . . . . ?
C8 C9 C10 C11 1.2(6) . . . . ?
F10 C10 C11 F11 -1.5(6) . . . . ?
C9 C10 C11 F11 179.5(4) . . . . ?
F10 C10 C11 C12 178.3(4) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
F11 C11 C12 F12 1.5(6) . . . . ?
C10 C11 C12 F12 -178.3(4) . . . . ?
F11 C11 C12 C13 179.3(3) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C9 C8 C13 F13 176.6(3) . . . . ?
C7 C8 C13 F13 -3.1(5) . . . . ?
C9 C8 C13 C12 -1.0(6) . . . . ?
C7 C8 C13 C12 179.4(4) . . . . ?
F12 C12 C13 F13 1.7(5) . . . . ?
C11 C12 C13 F13 -176.2(3) . . . . ?
F12 C12 C13 C8 179.2(3) . . . . ?
C11 C12 C13 C8 1.4(6) . . . . ?
C15A P1A C1A C2A 14.0(4) . . . . ?
C14A P1A C1A C2A 135.5(3) . . . . ?
C7A P1A C1A C2A -105.0(3) . . . . ?
C15A P1A C1A C6A -164.9(3) . . . . ?
C14A P1A C1A C6A -43.5(4) . . . . ?
C7A P1A C1A C6A 76.0(4) . . . . ?
C6A C1A C2A C3A -0.1(6) . . . . ?
P1A C1A C2A C3A -179.0(3) . . . . ?
C1A C2A C3A C4A -0.7(6) . . . . ?
C2A C3A C4A C5A 0.6(7) . . . . ?
C3A C4A C5A C6A 0.2(7) . . . . ?
C4A C5A C6A C1A -1.0(7) . . . . ?
C2A C1A C6A C5A 0.9(6) . . . . ?
P1A C1A C6A C5A 179.9(3) . . . . ?
C15A P1A C7A C8A 178.9(3) . . . . ?
C1A P1A C7A C8A -59.8(3) . . . . ?
C14A P1A C7A C8A 60.5(3) . . . . ?
P1A C7A C8A C13A 90.3(4) . . . . ?
P1A C7A C8A C9A -87.1(4) . . . . ?
C13A C8A C9A F9A 178.7(3) . . . . ?
C7A C8A C9A F9A -3.7(5) . . . . ?
C13A C8A C9A C10A -2.5(6) . . . . ?
C7A C8A C9A C10A 175.0(4) . . . . ?
F9A C9A C10A F10A -1.3(6) . . . . ?
C8A C9A C10A F10A 180.0(3) . . . . ?
F9A C9A C10A C11A 179.0(3) . . . . ?
C8A C9A C10A C11A 0.2(6) . . . . ?
F10A C10A C11A F11A 1.3(6) . . . . ?
C9A C10A C11A F11A -179.0(3) . . . . ?
F10A C10A C11A C12A -178.0(4) . . . . ?
C9A C10A C11A C12A 1.7(6) . . . . ?
F11A C11A C12A F12A -2.4(6) . . . . ?
C10A C11A C12A F12A 176.9(4) . . . . ?
F11A C11A C12A C13A 179.5(4) . . . . ?
C10A C11A C12A C13A -1.2(6) . . . . ?
F12A C12A C13A F13A 0.9(6) . . . . ?
C11A C12A C13A F13A 179.0(4) . . . . ?
F12A C12A C13A C8A -179.4(4) . . . . ?
C11A C12A C13A C8A -1.3(6) . . . . ?
C9A C8A C13A F13A -177.3(3) . . . . ?
C7A C8A C13A F13A 5.2(5) . . . . ?
C9A C8A C13A C12A 3.1(6) . . . . ?
C7A C8A C13A C12A -174.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.096

# Attachment 'o8h6.cif'

data_o8h6
_database_code_depnum_ccdc_archive 'CCDC 795078'
#TrackingRef 'o8h6.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 F5 P, C24 H20 B'
_chemical_formula_sum            'C49 H37 B F5 P'
_chemical_formula_weight         762.57

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           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   32.7210(7)
_cell_length_b                   14.0835(3)
_cell_length_c                   17.1709(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.5470(10)
_cell_angle_gamma                90.00
_cell_volume                     7723.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9746
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3168
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13235
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6792
_reflns_number_gt                4974
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2006)'
_computing_publication_material  SHELXL-97

_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^ > 2\s(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^)+(0.0244P)^2^+17.6940P] 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         6792
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
P1 P 0.132106(19) 0.31283(5) 0.56941(4) 0.02135(15) Uani 1 1 d . . .
F1 F 0.18350(5) 0.44378(12) 0.44477(10) 0.0468(4) Uani 1 1 d . . .
F2 F 0.16099(8) 0.49792(14) 0.29050(12) 0.0779(7) Uani 1 1 d . . .
F3 F 0.08057(9) 0.54959(14) 0.22709(10) 0.0855(8) Uani 1 1 d . . .
F4 F 0.02299(6) 0.54892(14) 0.32076(11) 0.0720(6) Uani 1 1 d . . .
F5 F 0.04549(5) 0.49800(12) 0.47332(9) 0.0429(4) Uani 1 1 d . . .
C1 C 0.16666(7) 0.30107(17) 0.66517(13) 0.0211(5) Uani 1 1 d . . .
C2 C 0.20636(7) 0.34306(18) 0.68003(14) 0.0249(5) Uani 1 1 d . . .
H2 H 0.2153 0.3773 0.6390 0.030 Uiso 1 1 calc R . .
C3 C 0.23258(8) 0.33457(18) 0.75469(15) 0.0291(6) Uani 1 1 d . . .
H3 H 0.2596 0.3629 0.7651 0.035 Uiso 1 1 calc R . .
C4 C 0.21922(8) 0.28444(18) 0.81439(14) 0.0279(6) Uani 1 1 d . . .
H4 H 0.2373 0.2784 0.8656 0.034 Uiso 1 1 calc R . .
C5 C 0.18016(8) 0.24364(19) 0.79994(14) 0.0291(6) Uani 1 1 d . . .
H5 H 0.1714 0.2098 0.8412 0.035 Uiso 1 1 calc R . .
C6 C 0.15354(8) 0.25151(18) 0.72566(13) 0.0255(6) Uani 1 1 d . . .
H6 H 0.1265 0.2234 0.7160 0.031 Uiso 1 1 calc R . .
C7 C 0.08232(7) 0.26081(18) 0.56858(13) 0.0239(5) Uani 1 1 d . . .
C8 C 0.04803(8) 0.31317(19) 0.57890(14) 0.0295(6) Uani 1 1 d . . .
H8 H 0.0503 0.3799 0.5865 0.035 Uiso 1 1 calc R . .
C9 C 0.01058(8) 0.2676(2) 0.57813(17) 0.0379(7) Uani 1 1 d . . .
H9 H -0.0130 0.3037 0.5847 0.046 Uiso 1 1 calc R . .
C10 C 0.00687(8) 0.1707(2) 0.56802(16) 0.0363(7) Uani 1 1 d . . .
H10 H -0.0190 0.1402 0.5677 0.044 Uiso 1 1 calc R . .
C11 C 0.04107(9) 0.1184(2) 0.55835(17) 0.0383(7) Uani 1 1 d . . .
H11 H 0.0386 0.0516 0.5514 0.046 Uiso 1 1 calc R . .
C12 C 0.07873(8) 0.16240(19) 0.55862(16) 0.0334(6) Uani 1 1 d . . .
H12 H 0.1022 0.1260 0.5521 0.040 Uiso 1 1 calc R . .
C13 C 0.15164(8) 0.25481(17) 0.49172(14) 0.0250(5) Uani 1 1 d . . .
C14 C 0.19148(8) 0.21611(19) 0.50523(15) 0.0310(6) Uani 1 1 d . . .
H14 H 0.2092 0.2182 0.5570 0.037 Uiso 1 1 calc R . .
C15 C 0.20524(9) 0.1742(2) 0.44238(18) 0.0452(8) Uani 1 1 d . . .
H15 H 0.2324 0.1469 0.4512 0.054 Uiso 1 1 calc R . .
C16 C 0.17970(10) 0.1719(2) 0.36731(18) 0.0480(8) Uani 1 1 d . . .
H16 H 0.1896 0.1437 0.3246 0.058 Uiso 1 1 calc R . .
C17 C 0.13987(9) 0.2100(2) 0.35335(16) 0.0394(7) Uani 1 1 d . . .
H17 H 0.1226 0.2087 0.3012 0.047 Uiso 1 1 calc R . .
C18 C 0.12534(9) 0.25034(19) 0.41581(14) 0.0314(6) Uani 1 1 d . . .
H18 H 0.0977 0.2748 0.4071 0.038 Uiso 1 1 calc R . .
C19 C 0.12830(8) 0.44066(17) 0.54967(13) 0.0243(5) Uani 1 1 d . . .
H19A H 0.1080 0.4679 0.5786 0.029 Uiso 1 1 calc R . .
H19B H 0.1559 0.4697 0.5722 0.029 Uiso 1 1 calc R . .
C20 C 0.11536(8) 0.46876(17) 0.46363(14) 0.0252(6) Uani 1 1 d . . .
C21 C 0.14369(9) 0.47023(19) 0.41489(16) 0.0343(6) Uani 1 1 d . . .
C22 C 0.13248(12) 0.4973(2) 0.33565(18) 0.0502(9) Uani 1 1 d . . .
C23 C 0.09138(13) 0.5226(2) 0.30414(16) 0.0543(10) Uani 1 1 d . . .
C24 C 0.06261(10) 0.5216(2) 0.35097(17) 0.0460(8) Uani 1 1 d . . .
C25 C 0.07474(9) 0.49524(18) 0.42900(15) 0.0332(6) Uani 1 1 d . . .
B1 B 0.12858(9) 0.8061(2) 0.56190(16) 0.0245(6) Uani 1 1 d . . .
C26 C 0.08731(8) 0.7780(2) 0.59766(14) 0.0283(6) Uani 1 1 d . . .
C27 C 0.05997(9) 0.8464(2) 0.61541(16) 0.0414(7) Uani 1 1 d . . .
H27 H 0.0662 0.9114 0.6091 0.050 Uiso 1 1 calc R . .
C28 C 0.02377(10) 0.8234(3) 0.64205(19) 0.0563(9) Uani 1 1 d . . .
H28 H 0.0064 0.8725 0.6547 0.068 Uiso 1 1 calc R . .
C29 C 0.01333(10) 0.7303(3) 0.65002(18) 0.0559(10) Uani 1 1 d . . .
H29 H -0.0112 0.7144 0.6682 0.067 Uiso 1 1 calc R . .
C30 C 0.03878(9) 0.6602(3) 0.63138(19) 0.0506(8) Uani 1 1 d . . .
H30 H 0.0316 0.5954 0.6357 0.061 Uiso 1 1 calc R . .
C31 C 0.07500(8) 0.6843(2) 0.60624(16) 0.0364(7) Uani 1 1 d . . .
H31 H 0.0923 0.6346 0.5943 0.044 Uiso 1 1 calc R . .
C32 C 0.16284(7) 0.71902(17) 0.57334(13) 0.0226(5) Uani 1 1 d . . .
C33 C 0.17488(8) 0.67033(18) 0.64624(14) 0.0265(6) Uani 1 1 d . . .
H33 H 0.1606 0.6841 0.6875 0.032 Uiso 1 1 calc R . .
C34 C 0.20668(8) 0.60316(18) 0.66075(15) 0.0307(6) Uani 1 1 d . . .
H34 H 0.2133 0.5713 0.7107 0.037 Uiso 1 1 calc R . .
C35 C 0.22888(8) 0.58243(18) 0.60255(16) 0.0313(6) Uani 1 1 d . . .
H35 H 0.2511 0.5375 0.6126 0.038 Uiso 1 1 calc R . .
C36 C 0.21822(8) 0.62794(18) 0.52995(15) 0.0301(6) Uani 1 1 d . . .
H36 H 0.2329 0.6140 0.4893 0.036 Uiso 1 1 calc R . .
C37 C 0.18579(8) 0.69462(18) 0.51611(14) 0.0270(6) Uani 1 1 d . . .
H37 H 0.1790 0.7249 0.4655 0.032 Uiso 1 1 calc R . .
C38 C 0.10989(7) 0.83220(18) 0.46699(14) 0.0236(5) Uani 1 1 d . . .
C39 C 0.09421(7) 0.76141(19) 0.41113(14) 0.0268(6) Uani 1 1 d . . .
H39 H 0.0969 0.6970 0.4278 0.032 Uiso 1 1 calc R . .
C40 C 0.07488(8) 0.7810(2) 0.33242(15) 0.0315(6) Uani 1 1 d . . .
H40 H 0.0646 0.7305 0.2968 0.038 Uiso 1 1 calc R . .
C41 C 0.07054(8) 0.8739(2) 0.30606(15) 0.0361(7) Uani 1 1 d . . .
H41 H 0.0572 0.8879 0.2525 0.043 Uiso 1 1 calc R . .
C42 C 0.08589(9) 0.9461(2) 0.35864(16) 0.0384(7) Uani 1 1 d . . .
H42 H 0.0834 1.0102 0.3410 0.046 Uiso 1 1 calc R . .
C43 C 0.10503(8) 0.92520(19) 0.43763(15) 0.0316(6) Uani 1 1 d . . .
H43 H 0.1152 0.9761 0.4729 0.038 Uiso 1 1 calc R . .
C44 C 0.15519(8) 0.89706(18) 0.60715(14) 0.0261(6) Uani 1 1 d . . .
C45 C 0.18802(8) 0.93464(18) 0.57631(15) 0.0297(6) Uani 1 1 d . . .
H45 H 0.1937 0.9072 0.5292 0.036 Uiso 1 1 calc R . .
C46 C 0.21264(8) 1.00994(19) 0.61111(17) 0.0371(7) Uani 1 1 d . . .
H46 H 0.2347 1.0327 0.5882 0.044 Uiso 1 1 calc R . .
C47 C 0.20489(9) 1.0519(2) 0.67970(17) 0.0407(7) Uani 1 1 d . . .
H47 H 0.2210 1.1047 0.7033 0.049 Uiso 1 1 calc R . .
C48 C 0.17349(10) 1.01559(19) 0.71295(16) 0.0391(7) Uani 1 1 d . . .
H48 H 0.1682 1.0429 0.7604 0.047 Uiso 1 1 calc R . .
C49 C 0.14953(9) 0.93943(18) 0.67768(14) 0.0322(6) Uani 1 1 d . . .
H49 H 0.1284 0.9151 0.7025 0.039 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 0.0218(3) 0.0231(3) 0.0181(3) -0.0016(3) 0.0019(2) 0.0008(3)
F1 0.0439(10) 0.0404(10) 0.0625(11) -0.0064(9) 0.0258(8) -0.0083(8)
F2 0.142(2) 0.0514(12) 0.0617(12) -0.0072(10) 0.0679(14) -0.0229(13)
F3 0.172(2) 0.0512(12) 0.0221(9) 0.0081(9) -0.0020(11) -0.0181(14)
F4 0.0745(14) 0.0567(13) 0.0601(12) 0.0124(10) -0.0395(10) 0.0005(11)
F5 0.0312(8) 0.0435(10) 0.0500(10) 0.0054(8) 0.0002(7) 0.0032(8)
C1 0.0220(12) 0.0216(13) 0.0182(11) -0.0026(10) 0.0009(9) 0.0047(10)
C2 0.0260(13) 0.0261(14) 0.0228(12) -0.0005(11) 0.0058(10) 0.0012(11)
C3 0.0240(13) 0.0312(15) 0.0308(14) -0.0044(12) 0.0029(11) 0.0020(11)
C4 0.0334(14) 0.0275(14) 0.0196(12) -0.0034(11) -0.0013(10) 0.0094(12)
C5 0.0371(15) 0.0293(15) 0.0212(12) 0.0012(11) 0.0067(11) 0.0044(12)
C6 0.0275(13) 0.0279(14) 0.0213(12) -0.0020(11) 0.0058(10) 0.0016(11)
C7 0.0225(12) 0.0289(14) 0.0191(12) -0.0015(11) 0.0019(10) 0.0016(11)
C8 0.0313(14) 0.0276(14) 0.0307(14) -0.0014(12) 0.0087(11) -0.0005(12)
C9 0.0296(15) 0.0414(17) 0.0455(17) 0.0046(14) 0.0141(13) 0.0036(13)
C10 0.0255(14) 0.0419(18) 0.0407(16) 0.0052(14) 0.0050(12) -0.0073(13)
C11 0.0362(16) 0.0274(15) 0.0487(17) -0.0014(13) 0.0033(13) -0.0051(13)
C12 0.0287(14) 0.0282(15) 0.0431(16) -0.0025(12) 0.0068(12) 0.0011(12)
C13 0.0313(14) 0.0225(13) 0.0220(12) -0.0037(10) 0.0078(10) -0.0037(11)
C14 0.0293(14) 0.0333(15) 0.0309(14) -0.0093(12) 0.0076(11) -0.0017(12)
C15 0.0361(16) 0.050(2) 0.0517(18) -0.0220(16) 0.0154(14) 0.0003(14)
C16 0.0484(19) 0.059(2) 0.0424(17) -0.0276(16) 0.0229(15) -0.0116(16)
C17 0.0500(18) 0.0438(18) 0.0244(14) -0.0126(13) 0.0083(13) -0.0111(15)
C18 0.0382(15) 0.0283(15) 0.0270(13) -0.0040(11) 0.0053(11) -0.0017(12)
C19 0.0269(13) 0.0217(13) 0.0227(13) -0.0017(10) 0.0023(10) -0.0002(11)
C20 0.0338(14) 0.0199(13) 0.0199(12) -0.0002(10) 0.0012(11) -0.0032(11)
C21 0.0429(17) 0.0262(15) 0.0353(15) -0.0035(12) 0.0118(13) -0.0072(13)
C22 0.096(3) 0.0298(17) 0.0349(17) -0.0029(14) 0.0355(18) -0.0162(18)
C23 0.103(3) 0.0321(17) 0.0180(15) 0.0004(13) -0.0077(17) -0.0099(19)
C24 0.060(2) 0.0327(17) 0.0335(17) 0.0020(13) -0.0159(15) -0.0039(15)
C25 0.0428(16) 0.0246(15) 0.0275(14) 0.0018(12) -0.0025(12) -0.0032(13)
B1 0.0270(15) 0.0249(15) 0.0204(13) -0.0011(12) 0.0027(11) 0.0013(13)
C26 0.0254(13) 0.0386(16) 0.0200(12) 0.0037(11) 0.0028(10) 0.0041(12)
C27 0.0394(16) 0.0476(19) 0.0391(16) 0.0060(14) 0.0128(13) 0.0159(14)
C28 0.0409(18) 0.085(3) 0.0472(19) 0.0046(19) 0.0189(15) 0.0216(19)
C29 0.0313(17) 0.098(3) 0.0417(18) 0.0190(19) 0.0141(14) 0.0001(19)
C30 0.0323(16) 0.062(2) 0.057(2) 0.0157(17) 0.0098(15) -0.0084(16)
C31 0.0272(14) 0.0399(17) 0.0415(16) 0.0020(14) 0.0061(12) -0.0026(13)
C32 0.0227(12) 0.0217(13) 0.0219(12) -0.0023(10) 0.0015(10) -0.0056(10)
C33 0.0268(13) 0.0267(14) 0.0251(13) -0.0003(11) 0.0034(10) -0.0026(11)
C34 0.0306(14) 0.0274(14) 0.0293(14) 0.0076(12) -0.0040(11) -0.0049(12)
C35 0.0252(13) 0.0234(14) 0.0424(16) 0.0010(12) 0.0010(12) 0.0004(11)
C36 0.0262(13) 0.0298(15) 0.0349(14) -0.0025(12) 0.0079(11) -0.0005(12)
C37 0.0287(13) 0.0274(14) 0.0240(13) 0.0023(11) 0.0040(10) 0.0006(11)
C38 0.0201(12) 0.0278(14) 0.0235(12) 0.0000(11) 0.0062(10) 0.0002(11)
C39 0.0224(13) 0.0321(15) 0.0258(13) 0.0020(11) 0.0046(10) -0.0016(11)
C40 0.0275(14) 0.0388(16) 0.0275(14) -0.0025(12) 0.0044(11) -0.0027(12)
C41 0.0308(15) 0.0507(19) 0.0239(14) 0.0073(13) -0.0005(11) 0.0019(14)
C42 0.0453(17) 0.0344(16) 0.0331(15) 0.0123(13) 0.0028(13) 0.0009(14)
C43 0.0324(15) 0.0294(15) 0.0303(14) 0.0013(12) 0.0011(11) -0.0005(12)
C44 0.0296(14) 0.0232(13) 0.0228(13) 0.0026(11) -0.0004(10) 0.0058(11)
C45 0.0269(13) 0.0270(14) 0.0318(14) -0.0035(12) -0.0011(11) 0.0018(12)
C46 0.0302(14) 0.0299(15) 0.0469(17) 0.0016(13) -0.0007(13) 0.0004(12)
C47 0.0448(17) 0.0259(15) 0.0407(16) -0.0048(13) -0.0143(14) 0.0012(14)
C48 0.062(2) 0.0243(15) 0.0247(14) -0.0014(12) -0.0036(13) 0.0047(14)
C49 0.0471(16) 0.0243(14) 0.0232(13) 0.0035(11) 0.0036(12) 0.0033(13)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 1.783(2) . ?
P1 C1 1.789(2) . ?
P1 C13 1.796(2) . ?
P1 C19 1.831(2) . ?
F1 C21 1.345(3) . ?
F2 C22 1.336(3) . ?
F3 C23 1.348(3) . ?
F4 C24 1.344(4) . ?
F5 C25 1.346(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.399(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C7 C12 1.398(4) . ?
C8 C9 1.381(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 C18 1.399(3) . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.499(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.377(4) . ?
C20 C25 1.384(4) . ?
C21 C22 1.384(4) . ?
C22 C23 1.383(5) . ?
C23 C24 1.364(5) . ?
C24 C25 1.364(4) . ?
B1 C32 1.644(4) . ?
B1 C44 1.646(4) . ?
B1 C26 1.648(4) . ?
B1 C38 1.653(3) . ?
C26 C27 1.393(4) . ?
C26 C31 1.396(4) . ?
C27 C28 1.397(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.369(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.374(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C37 1.403(3) . ?
C32 C33 1.406(3) . ?
C33 C34 1.388(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.377(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.398(4) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C43 1.400(3) . ?
C38 C39 1.401(3) . ?
C39 C40 1.390(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.382(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.380(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.396(4) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C49 1.398(3) . ?
C44 C45 1.401(4) . ?
C45 C46 1.386(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.389(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.377(4) . ?
C47 H47 0.9500 . ?
C48 C49 1.388(4) . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?

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
C7 P1 C1 111.29(11) . . ?
C7 P1 C13 106.20(11) . . ?
C1 P1 C13 112.62(11) . . ?
C7 P1 C19 112.16(12) . . ?
C1 P1 C19 105.37(11) . . ?
C13 P1 C19 109.31(11) . . ?
C6 C1 C2 120.0(2) . . ?
C6 C1 P1 119.71(18) . . ?
C2 C1 P1 120.31(18) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 119.6(2) . . ?
C8 C7 P1 123.0(2) . . ?
C12 C7 P1 117.43(19) . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C14 C13 C18 120.3(2) . . ?
C14 C13 P1 121.89(19) . . ?
C18 C13 P1 117.81(19) . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 119.6(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C20 C19 P1 115.80(17) . . ?
C20 C19 H19A 108.3 . . ?
P1 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
P1 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C21 C20 C25 116.4(2) . . ?
C21 C20 C19 121.3(2) . . ?
C25 C20 C19 122.3(2) . . ?
F1 C21 C20 119.2(2) . . ?
F1 C21 C22 118.6(3) . . ?
C20 C21 C22 122.1(3) . . ?
F2 C22 C23 120.9(3) . . ?
F2 C22 C21 120.2(3) . . ?
C23 C22 C21 118.9(3) . . ?
F3 C23 C24 120.9(3) . . ?
F3 C23 C22 118.8(3) . . ?
C24 C23 C22 120.3(3) . . ?
F4 C24 C25 120.5(3) . . ?
F4 C24 C23 120.1(3) . . ?
C25 C24 C23 119.4(3) . . ?
F5 C25 C24 117.2(3) . . ?
F5 C25 C20 119.9(2) . . ?
C24 C25 C20 122.9(3) . . ?
C32 B1 C44 104.30(19) . . ?
C32 B1 C26 111.7(2) . . ?
C44 B1 C26 113.8(2) . . ?
C32 B1 C38 112.4(2) . . ?
C44 B1 C38 109.7(2) . . ?
C26 B1 C38 105.26(19) . . ?
C27 C26 C31 114.6(2) . . ?
C27 C26 B1 122.2(2) . . ?
C31 C26 B1 123.0(2) . . ?
C26 C27 C28 122.8(3) . . ?
C26 C27 H27 118.6 . . ?
C28 C27 H27 118.6 . . ?
C29 C28 C27 120.2(3) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 119.2(3) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C29 C30 C31 119.9(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C26 123.3(3) . . ?
C30 C31 H31 118.3 . . ?
C26 C31 H31 118.3 . . ?
C37 C32 C33 114.5(2) . . ?
C37 C32 B1 123.6(2) . . ?
C33 C32 B1 121.5(2) . . ?
C34 C33 C32 123.1(2) . . ?
C34 C33 H33 118.4 . . ?
C32 C33 H33 118.4 . . ?
C33 C34 C35 120.2(2) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C36 C35 C34 119.0(2) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C35 C36 C37 120.0(2) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C32 123.2(2) . . ?
C36 C37 H37 118.4 . . ?
C32 C37 H37 118.4 . . ?
C43 C38 C39 115.0(2) . . ?
C43 C38 B1 123.5(2) . . ?
C39 C38 B1 121.2(2) . . ?
C40 C39 C38 123.1(2) . . ?
C40 C39 H39 118.4 . . ?
C38 C39 H39 118.4 . . ?
C41 C40 C39 119.9(3) . . ?
C41 C40 H40 120.0 . . ?
C39 C40 H40 120.0 . . ?
C42 C41 C40 119.1(2) . . ?
C42 C41 H41 120.4 . . ?
C40 C41 H41 120.4 . . ?
C41 C42 C43 120.2(3) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C42 C43 C38 122.6(2) . . ?
C42 C43 H43 118.7 . . ?
C38 C43 H43 118.7 . . ?
C49 C44 C45 115.0(2) . . ?
C49 C44 B1 125.8(2) . . ?
C45 C44 B1 119.1(2) . . ?
C46 C45 C44 123.2(3) . . ?
C46 C45 H45 118.4 . . ?
C44 C45 H45 118.4 . . ?
C45 C46 C47 119.6(3) . . ?
C45 C46 H46 120.2 . . ?
C47 C46 H46 120.2 . . ?
C48 C47 C46 118.9(3) . . ?
C48 C47 H47 120.5 . . ?
C46 C47 H47 120.5 . . ?
C47 C48 C49 120.5(3) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
C48 C49 C44 122.6(3) . . ?
C48 C49 H49 118.7 . . ?
C44 C49 H49 118.7 . . ?

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
C7 P1 C1 C6 3.1(2) . . . . ?
C13 P1 C1 C6 -116.0(2) . . . . ?
C19 P1 C1 C6 124.9(2) . . . . ?
C7 P1 C1 C2 -175.52(19) . . . . ?
C13 P1 C1 C2 65.4(2) . . . . ?
C19 P1 C1 C2 -53.7(2) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
P1 C1 C2 C3 179.11(19) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
P1 C1 C6 C5 -179.16(19) . . . . ?
C1 P1 C7 C8 97.5(2) . . . . ?
C13 P1 C7 C8 -139.6(2) . . . . ?
C19 P1 C7 C8 -20.3(2) . . . . ?
C1 P1 C7 C12 -81.2(2) . . . . ?
C13 P1 C7 C12 41.7(2) . . . . ?
C19 P1 C7 C12 161.07(19) . . . . ?
C12 C7 C8 C9 -0.9(4) . . . . ?
P1 C7 C8 C9 -179.5(2) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
C8 C7 C12 C11 0.6(4) . . . . ?
P1 C7 C12 C11 179.3(2) . . . . ?
C7 P1 C13 C14 -129.4(2) . . . . ?
C1 P1 C13 C14 -7.3(3) . . . . ?
C19 P1 C13 C14 109.4(2) . . . . ?
C7 P1 C13 C18 51.2(2) . . . . ?
C1 P1 C13 C18 173.26(19) . . . . ?
C19 P1 C13 C18 -70.0(2) . . . . ?
C18 C13 C14 C15 1.0(4) . . . . ?
P1 C13 C14 C15 -178.4(2) . . . . ?
C13 C14 C15 C16 0.6(5) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C16 C17 C18 C13 2.2(4) . . . . ?
C14 C13 C18 C17 -2.4(4) . . . . ?
P1 C13 C18 C17 177.1(2) . . . . ?
C7 P1 C19 C20 -81.3(2) . . . . ?
C1 P1 C19 C20 157.44(18) . . . . ?
C13 P1 C19 C20 36.2(2) . . . . ?
P1 C19 C20 C21 -80.5(3) . . . . ?
P1 C19 C20 C25 100.0(3) . . . . ?
C25 C20 C21 F1 -178.9(2) . . . . ?
C19 C20 C21 F1 1.6(4) . . . . ?
C25 C20 C21 C22 0.4(4) . . . . ?
C19 C20 C21 C22 -179.0(2) . . . . ?
F1 C21 C22 F2 -0.8(4) . . . . ?
C20 C21 C22 F2 179.8(2) . . . . ?
F1 C21 C22 C23 178.6(3) . . . . ?
C20 C21 C22 C23 -0.8(4) . . . . ?
F2 C22 C23 F3 -1.1(4) . . . . ?
C21 C22 C23 F3 179.5(3) . . . . ?
F2 C22 C23 C24 -180.0(3) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
F3 C23 C24 F4 -0.8(5) . . . . ?
C22 C23 C24 F4 178.0(3) . . . . ?
F3 C23 C24 C25 -179.0(3) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
F4 C24 C25 F5 0.0(4) . . . . ?
C23 C24 C25 F5 178.2(3) . . . . ?
F4 C24 C25 C20 -178.4(2) . . . . ?
C23 C24 C25 C20 -0.2(4) . . . . ?
C21 C20 C25 F5 -178.3(2) . . . . ?
C19 C20 C25 F5 1.2(4) . . . . ?
C21 C20 C25 C24 0.0(4) . . . . ?
C19 C20 C25 C24 179.5(3) . . . . ?
C32 B1 C26 C27 161.7(2) . . . . ?
C44 B1 C26 C27 44.0(3) . . . . ?
C38 B1 C26 C27 -76.1(3) . . . . ?
C32 B1 C26 C31 -23.8(3) . . . . ?
C44 B1 C26 C31 -141.6(2) . . . . ?
C38 B1 C26 C31 98.4(3) . . . . ?
C31 C26 C27 C28 1.9(4) . . . . ?
B1 C26 C27 C28 176.8(3) . . . . ?
C26 C27 C28 C29 -1.5(5) . . . . ?
C27 C28 C29 C30 -0.1(5) . . . . ?
C28 C29 C30 C31 1.2(5) . . . . ?
C29 C30 C31 C26 -0.7(5) . . . . ?
C27 C26 C31 C30 -0.8(4) . . . . ?
B1 C26 C31 C30 -175.6(2) . . . . ?
C44 B1 C32 C37 -95.4(3) . . . . ?
C26 B1 C32 C37 141.3(2) . . . . ?
C38 B1 C32 C37 23.3(3) . . . . ?
C44 B1 C32 C33 76.9(3) . . . . ?
C26 B1 C32 C33 -46.3(3) . . . . ?
C38 B1 C32 C33 -164.3(2) . . . . ?
C37 C32 C33 C34 -0.3(4) . . . . ?
B1 C32 C33 C34 -173.3(2) . . . . ?
C32 C33 C34 C35 1.2(4) . . . . ?
C33 C34 C35 C36 -1.4(4) . . . . ?
C34 C35 C36 C37 0.7(4) . . . . ?
C35 C36 C37 C32 0.2(4) . . . . ?
C33 C32 C37 C36 -0.4(4) . . . . ?
B1 C32 C37 C36 172.4(2) . . . . ?
C32 B1 C38 C43 -135.7(2) . . . . ?
C44 B1 C38 C43 -20.2(3) . . . . ?
C26 B1 C38 C43 102.6(3) . . . . ?
C32 B1 C38 C39 50.1(3) . . . . ?
C44 B1 C38 C39 165.6(2) . . . . ?
C26 B1 C38 C39 -71.6(3) . . . . ?
C43 C38 C39 C40 -0.5(3) . . . . ?
B1 C38 C39 C40 174.1(2) . . . . ?
C38 C39 C40 C41 0.2(4) . . . . ?
C39 C40 C41 C42 0.5(4) . . . . ?
C40 C41 C42 C43 -0.8(4) . . . . ?
C41 C42 C43 C38 0.5(4) . . . . ?
C39 C38 C43 C42 0.2(4) . . . . ?
B1 C38 C43 C42 -174.4(2) . . . . ?
C32 B1 C44 C49 -111.3(3) . . . . ?
C26 B1 C44 C49 10.6(3) . . . . ?
C38 B1 C44 C49 128.2(2) . . . . ?
C32 B1 C44 C45 65.4(3) . . . . ?
C26 B1 C44 C45 -172.7(2) . . . . ?
C38 B1 C44 C45 -55.1(3) . . . . ?
C49 C44 C45 C46 -1.7(4) . . . . ?
B1 C44 C45 C46 -178.8(2) . . . . ?
C44 C45 C46 C47 -0.4(4) . . . . ?
C45 C46 C47 C48 1.9(4) . . . . ?
C46 C47 C48 C49 -1.1(4) . . . . ?
C47 C48 C49 C44 -1.2(4) . . . . ?
C45 C44 C49 C48 2.5(4) . . . . ?
B1 C44 C49 C48 179.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.048