# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2007

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Gerhard Erker'
_publ_contact_author_address     
;
Organisch-Chemisches Institut
Universitaet Muenster
Corrensstr. 40
Muenster
NRW
48149
GERMANY
;

_publ_contact_author_email       ERKER@UNI-MUENSTER.DE

_publ_section_title              
;Rapid Intramolecular Heterolytic Dihydrogen Activation
by a Four-membered Heterocyclic Phosphane-Borane Adduct
;
loop_
_publ_author_name
G.Erker
'Roland Frohlich'
'Stefan Grimme'
'Gerald Kehr'
'Patrick Spies'
D.W.Stephan

# Attachment 'ERK4107.CIF'

data_erk4107
_database_code_depnum_ccdc_archive 'CCDC 650365'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H28 B F10 P'
_chemical_formula_weight         644.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   12.3680(3)
_cell_length_b                   18.5413(5)
_cell_length_c                   13.1716(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.361(2)
_cell_angle_gamma                90.00
_cell_volume                     3001.90(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5119
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_exptl_absorpt_coefficient_mu    1.572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_T_max  0.7984
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21035
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.77
_diffrn_reflns_theta_max         67.44
_reflns_number_total             5312
_reflns_number_gt                4566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0839P)^2^+1.3205P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'at P and B from difmap, other geom'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5312
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1355
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.83648(4) 0.03438(3) 0.18487(4) 0.03834(17) Uani 1 1 d . . .
H10P H 0.7965(17) 0.0043(12) 0.1062(15) 0.038(5) Uiso 1 1 d . . .
C1 C 0.97726(17) 0.04895(12) 0.16449(17) 0.0442(5) Uani 1 1 d . . .
H1A H 0.9807 0.0818 0.1066 0.053 Uiso 1 1 calc R . .
H1B H 1.0159 0.0716 0.2252 0.053 Uiso 1 1 calc R . .
C2 C 1.03277(17) -0.02229(12) 0.14297(17) 0.0439(5) Uani 1 1 d . . .
H2A H 0.9934 -0.0454 0.0829 0.053 Uiso 1 1 calc R . .
H2B H 1.0307 -0.0548 0.2014 0.053 Uiso 1 1 calc R . .
B1 B 1.1589(2) -0.00855(14) 0.12264(18) 0.0424(5) Uani 1 1 d . . .
H10B H 1.1583(18) 0.0326(12) 0.0564(17) 0.044(6) Uiso 1 1 d . . .
C11 C 0.75095(17) 0.11198(12) 0.19956(15) 0.0410(5) Uani 1 1 d . . .
C12 C 0.78688(18) 0.18410(12) 0.19788(15) 0.0446(5) Uani 1 1 d . . .
C121 C 0.9032(2) 0.20768(13) 0.1974(2) 0.0576(6) Uani 1 1 d . . .
H12A H 0.9078 0.2596 0.2055 0.086 Uiso 1 1 calc R . .
H12B H 0.9288 0.1941 0.1331 0.086 Uiso 1 1 calc R . .
H12C H 0.9479 0.1846 0.2533 0.086 Uiso 1 1 calc R . .
C13 C 0.7098(2) 0.23877(13) 0.19755(16) 0.0522(6) Uani 1 1 d . . .
H13 H 0.7333 0.2869 0.1960 0.063 Uiso 1 1 calc R . .
C14 C 0.6000(2) 0.22515(15) 0.19940(17) 0.0561(6) Uani 1 1 d . . .
C141 C 0.5187(3) 0.28661(18) 0.1947(2) 0.0761(9) Uani 1 1 d . . .
H14A H 0.4626 0.2788 0.1382 0.114 Uiso 1 1 calc R . .
H14B H 0.5557 0.3317 0.1846 0.114 Uiso 1 1 calc R . .
H14C H 0.4858 0.2887 0.2581 0.114 Uiso 1 1 calc R . .
C15 C 0.5676(2) 0.15451(15) 0.20423(18) 0.0556(6) Uani 1 1 d . . .
H15 H 0.4935 0.1446 0.2075 0.067 Uiso 1 1 calc R . .
C16 C 0.63961(18) 0.09722(13) 0.20448(17) 0.0482(5) Uani 1 1 d . . .
C161 C 0.5946(2) 0.02123(15) 0.2103(3) 0.0692(7) Uani 1 1 d . . .
H16A H 0.5161 0.0233 0.2088 0.104 Uiso 1 1 calc R . .
H16B H 0.6255 -0.0014 0.2733 0.104 Uiso 1 1 calc R . .
H16C H 0.6135 -0.0067 0.1526 0.104 Uiso 1 1 calc R . .
C21 C 0.83400(17) -0.03328(11) 0.28267(16) 0.0418(5) Uani 1 1 d . . .
C22 C 0.85645(18) -0.01342(13) 0.38629(16) 0.0462(5) Uani 1 1 d . . .
C221 C 0.8662(2) 0.06416(14) 0.41971(18) 0.0580(6) Uani 1 1 d . . .
H22A H 0.8930 0.0663 0.4917 0.087 Uiso 1 1 calc R . .
H22B H 0.7954 0.0871 0.4087 0.087 Uiso 1 1 calc R . .
H22C H 0.9165 0.0890 0.3803 0.087 Uiso 1 1 calc R . .
C23 C 0.8667(2) -0.06739(14) 0.45893(18) 0.0562(6) Uani 1 1 d . . .
H23 H 0.8821 -0.0546 0.5281 0.067 Uiso 1 1 calc R . .
C24 C 0.8552(2) -0.13969(14) 0.4336(2) 0.0622(7) Uani 1 1 d . . .
C241 C 0.8714(3) -0.19787(18) 0.5141(3) 0.0913(11) Uani 1 1 d . . .
H24A H 0.9432 -0.2188 0.5138 0.137 Uiso 1 1 calc R . .
H24B H 0.8167 -0.2351 0.4996 0.137 Uiso 1 1 calc R . .
H24C H 0.8647 -0.1771 0.5807 0.137 Uiso 1 1 calc R . .
C25 C 0.8294(2) -0.15763(13) 0.3319(2) 0.0603(7) Uani 1 1 d . . .
H25 H 0.8192 -0.2065 0.3145 0.072 Uiso 1 1 calc R . .
C26 C 0.8177(2) -0.10629(12) 0.25431(18) 0.0499(5) Uani 1 1 d . . .
C261 C 0.7881(3) -0.13194(14) 0.1463(2) 0.0653(7) Uani 1 1 d . . .
H26A H 0.7719 -0.1831 0.1467 0.098 Uiso 1 1 calc R . .
H26B H 0.8486 -0.1234 0.1069 0.098 Uiso 1 1 calc R . .
H26C H 0.7247 -0.1058 0.1159 0.098 Uiso 1 1 calc R . .
C31 C 1.22809(17) 0.02550(12) 0.22576(17) 0.0438(5) Uani 1 1 d . . .
C32 C 1.2561(2) 0.09787(13) 0.2364(2) 0.0557(6) Uani 1 1 d . . .
F32 F 1.22375(16) 0.14493(8) 0.16093(14) 0.0818(5) Uani 1 1 d . . .
C33 C 1.3155(2) 0.12639(15) 0.3205(2) 0.0669(7) Uani 1 1 d . . .
F33 F 1.33844(17) 0.19771(10) 0.32605(18) 0.1004(7) Uani 1 1 d . . .
C34 C 1.3526(2) 0.08307(18) 0.4003(2) 0.0721(8) Uani 1 1 d . . .
F34 F 1.41024(16) 0.10984(13) 0.48458(16) 0.1104(8) Uani 1 1 d . . .
C35 C 1.3273(2) 0.01071(17) 0.39581(19) 0.0647(7) Uani 1 1 d . . .
F35 F 1.36057(17) -0.03315(12) 0.47431(13) 0.0952(6) Uani 1 1 d . . .
C36 C 1.2649(2) -0.01560(13) 0.31016(17) 0.0503(5) Uani 1 1 d . . .
F36 F 1.23892(15) -0.08621(8) 0.31194(11) 0.0701(4) Uani 1 1 d . . .
C41 C 1.22252(18) -0.08142(12) 0.08990(15) 0.0435(5) Uani 1 1 d . . .
C42 C 1.33019(19) -0.07562(14) 0.06985(17) 0.0511(6) Uani 1 1 d . . .
F42 F 1.37609(11) -0.00928(9) 0.06799(12) 0.0690(4) Uani 1 1 d . . .
C43 C 1.3957(2) -0.13298(17) 0.05185(18) 0.0618(7) Uani 1 1 d . . .
F43 F 1.50090(12) -0.12312(12) 0.03740(13) 0.0895(6) Uani 1 1 d . . .
C44 C 1.3532(3) -0.20144(16) 0.04881(17) 0.0646(8) Uani 1 1 d . . .
F44 F 1.41554(17) -0.25897(10) 0.03396(12) 0.0923(6) Uani 1 1 d . . .
C45 C 1.2456(3) -0.21035(13) 0.06185(17) 0.0590(7) Uani 1 1 d . . .
F45 F 1.20114(18) -0.27649(8) 0.05544(13) 0.0857(6) Uani 1 1 d . . .
C46 C 1.1839(2) -0.15136(13) 0.08271(16) 0.0508(5) Uani 1 1 d . . .
F46 F 1.07917(13) -0.16621(8) 0.09734(12) 0.0697(4) Uani 1 1 d . . .

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 0.0415(3) 0.0379(3) 0.0356(3) -0.0014(2) 0.0040(2) -0.0007(2)
C1 0.0435(11) 0.0451(12) 0.0445(11) 0.0033(9) 0.0073(9) 0.0006(9)
C2 0.0439(11) 0.0437(12) 0.0441(11) 0.0001(9) 0.0046(9) 0.0014(9)
B1 0.0445(13) 0.0426(13) 0.0400(12) 0.0013(10) 0.0039(10) 0.0021(10)
C11 0.0434(11) 0.0446(12) 0.0340(10) -0.0020(8) -0.0003(8) 0.0016(9)
C12 0.0541(13) 0.0439(12) 0.0350(10) -0.0023(9) 0.0011(9) 0.0023(10)
C121 0.0601(15) 0.0385(12) 0.0738(16) -0.0008(11) 0.0052(12) -0.0044(10)
C13 0.0703(16) 0.0442(13) 0.0409(12) -0.0014(9) 0.0008(10) 0.0110(11)
C14 0.0672(16) 0.0623(16) 0.0376(11) -0.0025(10) 0.0013(10) 0.0210(12)
C141 0.082(2) 0.080(2) 0.0657(17) 0.0020(14) 0.0081(14) 0.0379(16)
C15 0.0463(12) 0.0696(17) 0.0507(13) -0.0051(12) 0.0040(10) 0.0128(11)
C16 0.0445(12) 0.0542(14) 0.0452(12) -0.0066(10) 0.0010(9) 0.0018(10)
C161 0.0474(14) 0.0651(17) 0.095(2) -0.0091(15) 0.0088(13) -0.0105(12)
C21 0.0466(11) 0.0377(11) 0.0420(11) 0.0021(9) 0.0091(9) 0.0004(9)
C22 0.0491(12) 0.0470(13) 0.0435(11) 0.0017(9) 0.0094(9) 0.0048(10)
C221 0.0770(17) 0.0540(14) 0.0408(12) -0.0046(10) -0.0034(11) 0.0012(12)
C23 0.0647(15) 0.0609(15) 0.0447(12) 0.0089(11) 0.0129(11) 0.0117(12)
C24 0.0724(17) 0.0532(15) 0.0651(16) 0.0175(12) 0.0265(13) 0.0122(12)
C241 0.128(3) 0.067(2) 0.084(2) 0.0331(17) 0.037(2) 0.0235(19)
C25 0.0732(17) 0.0396(13) 0.0728(17) 0.0074(11) 0.0287(13) 0.0018(11)
C26 0.0562(13) 0.0397(12) 0.0565(13) -0.0018(10) 0.0181(10) -0.0023(10)
C261 0.090(2) 0.0429(14) 0.0654(16) -0.0120(12) 0.0181(14) -0.0124(13)
C31 0.0409(11) 0.0416(12) 0.0494(12) -0.0041(9) 0.0068(9) 0.0032(9)
C32 0.0495(13) 0.0484(14) 0.0708(16) -0.0075(12) 0.0134(11) -0.0001(10)
F32 0.1017(13) 0.0431(8) 0.1011(12) 0.0109(8) 0.0137(10) -0.0027(8)
C33 0.0555(15) 0.0575(16) 0.090(2) -0.0261(15) 0.0175(14) -0.0105(13)
F33 0.0963(13) 0.0633(11) 0.1459(17) -0.0445(11) 0.0327(12) -0.0305(10)
C34 0.0507(14) 0.086(2) 0.0792(19) -0.0427(17) 0.0049(13) -0.0066(14)
F34 0.0789(12) 0.1458(19) 0.1013(14) -0.0665(13) -0.0132(10) -0.0146(12)
C35 0.0574(15) 0.084(2) 0.0504(14) -0.0093(13) -0.0025(11) 0.0160(14)
F35 0.1026(14) 0.1208(16) 0.0564(9) -0.0045(10) -0.0173(9) 0.0262(12)
C36 0.0568(13) 0.0457(13) 0.0481(12) -0.0094(10) 0.0043(10) 0.0052(10)
F36 0.1096(13) 0.0475(8) 0.0513(8) 0.0039(6) -0.0002(8) 0.0060(8)
C41 0.0492(12) 0.0477(12) 0.0329(10) -0.0001(9) 0.0015(8) 0.0047(10)
C42 0.0479(12) 0.0642(15) 0.0402(11) -0.0070(10) 0.0000(9) 0.0066(11)
F42 0.0468(8) 0.0784(11) 0.0829(10) -0.0145(8) 0.0116(7) -0.0102(7)
C43 0.0538(14) 0.087(2) 0.0428(12) -0.0095(12) -0.0023(10) 0.0211(14)
F43 0.0477(8) 0.1349(17) 0.0845(11) -0.0277(11) 0.0015(8) 0.0248(9)
C44 0.0836(19) 0.0729(19) 0.0356(12) -0.0018(11) -0.0007(11) 0.0381(15)
F44 0.1230(15) 0.0934(13) 0.0589(9) -0.0055(8) 0.0029(9) 0.0668(12)
C45 0.094(2) 0.0450(14) 0.0380(12) 0.0002(10) 0.0075(12) 0.0116(13)
F45 0.1436(17) 0.0424(8) 0.0743(11) -0.0021(7) 0.0256(10) 0.0070(9)
C46 0.0629(14) 0.0502(13) 0.0401(11) 0.0007(10) 0.0096(10) 0.0042(11)
F46 0.0790(10) 0.0479(8) 0.0872(11) -0.0068(7) 0.0314(8) -0.0112(7)

_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 C21 1.801(2) . ?
P1 C11 1.809(2) . ?
P1 C1 1.811(2) . ?
C1 C2 1.530(3) . ?
C2 B1 1.631(3) . ?
B1 C41 1.645(3) . ?
B1 C31 1.649(3) . ?
C11 C12 1.410(3) . ?
C11 C16 1.412(3) . ?
C12 C13 1.391(3) . ?
C12 C121 1.504(3) . ?
C13 C14 1.385(4) . ?
C14 C15 1.373(4) . ?
C14 C141 1.516(3) . ?
C15 C16 1.386(3) . ?
C16 C161 1.520(4) . ?
C21 C22 1.411(3) . ?
C21 C26 1.413(3) . ?
C22 C23 1.381(3) . ?
C22 C221 1.505(3) . ?
C23 C24 1.385(4) . ?
C24 C25 1.382(4) . ?
C24 C241 1.511(4) . ?
C25 C26 1.393(3) . ?
C26 C261 1.506(3) . ?
C31 C36 1.383(3) . ?
C31 C32 1.389(3) . ?
C32 F32 1.350(3) . ?
C32 C33 1.366(4) . ?
C33 F33 1.353(3) . ?
C33 C34 1.361(5) . ?
C34 F34 1.346(3) . ?
C34 C35 1.377(4) . ?
C35 F35 1.344(3) . ?
C35 C36 1.383(3) . ?
C36 F36 1.349(3) . ?
C41 C46 1.381(3) . ?
C41 C42 1.390(3) . ?
C42 F42 1.356(3) . ?
C42 C43 1.373(4) . ?
C43 F43 1.348(3) . ?
C43 C44 1.373(4) . ?
C44 F44 1.344(3) . ?
C44 C45 1.370(4) . ?
C45 F45 1.343(3) . ?
C45 C46 1.378(3) . ?
C46 F46 1.359(3) . ?

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
C21 P1 C11 114.90(10) . . ?
C21 P1 C1 107.63(10) . . ?
C11 P1 C1 118.71(10) . . ?
C2 C1 P1 110.93(15) . . ?
C1 C2 B1 110.64(18) . . ?
C2 B1 C41 114.13(19) . . ?
C2 B1 C31 110.07(18) . . ?
C41 B1 C31 108.09(17) . . ?
C12 C11 C16 119.7(2) . . ?
C12 C11 P1 124.30(16) . . ?
C16 C11 P1 115.81(16) . . ?
C13 C12 C11 118.3(2) . . ?
C13 C12 C121 116.3(2) . . ?
C11 C12 C121 125.4(2) . . ?
C14 C13 C12 122.7(2) . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 C141 121.6(3) . . ?
C13 C14 C141 120.6(3) . . ?
C14 C15 C16 122.7(2) . . ?
C15 C16 C11 118.7(2) . . ?
C15 C16 C161 118.1(2) . . ?
C11 C16 C161 123.1(2) . . ?
C22 C21 C26 120.8(2) . . ?
C22 C21 P1 119.53(16) . . ?
C26 C21 P1 119.45(16) . . ?
C23 C22 C21 118.3(2) . . ?
C23 C22 C221 119.5(2) . . ?
C21 C22 C221 122.21(19) . . ?
C22 C23 C24 122.4(2) . . ?
C25 C24 C23 118.2(2) . . ?
C25 C24 C241 120.5(3) . . ?
C23 C24 C241 121.3(3) . . ?
C24 C25 C26 122.7(2) . . ?
C25 C26 C21 117.4(2) . . ?
C25 C26 C261 118.2(2) . . ?
C21 C26 C261 124.4(2) . . ?
C36 C31 C32 113.3(2) . . ?
C36 C31 B1 123.1(2) . . ?
C32 C31 B1 123.6(2) . . ?
F32 C32 C33 115.8(2) . . ?
F32 C32 C31 120.0(2) . . ?
C33 C32 C31 124.2(3) . . ?
F33 C33 C34 119.0(3) . . ?
F33 C33 C32 120.9(3) . . ?
C34 C33 C32 120.2(3) . . ?
F34 C34 C33 121.4(3) . . ?
F34 C34 C35 119.4(3) . . ?
C33 C34 C35 119.1(2) . . ?
F35 C35 C34 120.5(2) . . ?
F35 C35 C36 120.6(3) . . ?
C34 C35 C36 118.8(3) . . ?
F36 C36 C31 119.4(2) . . ?
F36 C36 C35 116.1(2) . . ?
C31 C36 C35 124.4(2) . . ?
C46 C41 C42 113.0(2) . . ?
C46 C41 B1 128.1(2) . . ?
C42 C41 B1 118.9(2) . . ?
F42 C42 C43 116.3(2) . . ?
F42 C42 C41 119.0(2) . . ?
C43 C42 C41 124.7(3) . . ?
F43 C43 C44 119.6(2) . . ?
F43 C43 C42 121.1(3) . . ?
C44 C43 C42 119.3(3) . . ?
F44 C44 C45 120.3(3) . . ?
F44 C44 C43 120.9(3) . . ?
C45 C44 C43 118.8(2) . . ?
F45 C45 C44 119.9(2) . . ?
F45 C45 C46 120.4(3) . . ?
C44 C45 C46 119.7(3) . . ?
F46 C46 C45 115.1(2) . . ?
F46 C46 C41 120.5(2) . . ?
C45 C46 C41 124.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 P1 C1 C2 53.16(17) . . . . ?
C11 P1 C1 C2 -174.17(14) . . . . ?
P1 C1 C2 B1 178.96(14) . . . . ?
C1 C2 B1 C41 -175.45(17) . . . . ?
C1 C2 B1 C31 62.8(2) . . . . ?
C21 P1 C11 C12 128.36(18) . . . . ?
C1 P1 C11 C12 -1.1(2) . . . . ?
C21 P1 C11 C16 -56.97(19) . . . . ?
C1 P1 C11 C16 173.61(15) . . . . ?
C16 C11 C12 C13 -2.2(3) . . . . ?
P1 C11 C12 C13 172.27(16) . . . . ?
C16 C11 C12 C121 177.2(2) . . . . ?
P1 C11 C12 C121 -8.4(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C121 C12 C13 C14 -179.0(2) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C12 C13 C14 C141 -177.5(2) . . . . ?
C13 C14 C15 C16 -1.8(4) . . . . ?
C141 C14 C15 C16 177.3(2) . . . . ?
C14 C15 C16 C11 0.0(3) . . . . ?
C14 C15 C16 C161 179.8(2) . . . . ?
C12 C11 C16 C15 2.0(3) . . . . ?
P1 C11 C16 C15 -172.90(17) . . . . ?
C12 C11 C16 C161 -177.8(2) . . . . ?
P1 C11 C16 C161 7.3(3) . . . . ?
C11 P1 C21 C22 -54.0(2) . . . . ?
C1 P1 C21 C22 80.69(19) . . . . ?
C11 P1 C21 C26 130.75(18) . . . . ?
C1 P1 C21 C26 -94.6(2) . . . . ?
C26 C21 C22 C23 2.7(3) . . . . ?
P1 C21 C22 C23 -172.44(18) . . . . ?
C26 C21 C22 C221 -175.5(2) . . . . ?
P1 C21 C22 C221 9.3(3) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C221 C22 C23 C24 177.9(2) . . . . ?
C22 C23 C24 C25 -1.9(4) . . . . ?
C22 C23 C24 C241 177.5(3) . . . . ?
C23 C24 C25 C26 1.9(4) . . . . ?
C241 C24 C25 C26 -177.5(3) . . . . ?
C24 C25 C26 C21 0.3(4) . . . . ?
C24 C25 C26 C261 -179.3(3) . . . . ?
C22 C21 C26 C25 -2.7(3) . . . . ?
P1 C21 C26 C25 172.48(18) . . . . ?
C22 C21 C26 C261 176.9(2) . . . . ?
P1 C21 C26 C261 -7.9(3) . . . . ?
C2 B1 C31 C36 77.5(3) . . . . ?
C41 B1 C31 C36 -47.7(3) . . . . ?
C2 B1 C31 C32 -103.0(2) . . . . ?
C41 B1 C31 C32 131.7(2) . . . . ?
C36 C31 C32 F32 -178.6(2) . . . . ?
B1 C31 C32 F32 1.9(3) . . . . ?
C36 C31 C32 C33 1.0(3) . . . . ?
B1 C31 C32 C33 -178.5(2) . . . . ?
F32 C32 C33 F33 0.6(4) . . . . ?
C31 C32 C33 F33 -179.1(2) . . . . ?
F32 C32 C33 C34 -179.5(2) . . . . ?
C31 C32 C33 C34 0.9(4) . . . . ?
F33 C33 C34 F34 0.8(4) . . . . ?
C32 C33 C34 F34 -179.2(2) . . . . ?
F33 C33 C34 C35 178.6(2) . . . . ?
C32 C33 C34 C35 -1.4(4) . . . . ?
F34 C34 C35 F35 -0.6(4) . . . . ?
C33 C34 C35 F35 -178.5(2) . . . . ?
F34 C34 C35 C36 177.8(2) . . . . ?
C33 C34 C35 C36 0.0(4) . . . . ?
C32 C31 C36 F36 176.9(2) . . . . ?
B1 C31 C36 F36 -3.6(3) . . . . ?
C32 C31 C36 C35 -2.6(3) . . . . ?
B1 C31 C36 C35 176.9(2) . . . . ?
F35 C35 C36 F36 1.1(4) . . . . ?
C34 C35 C36 F36 -177.3(2) . . . . ?
F35 C35 C36 C31 -179.4(2) . . . . ?
C34 C35 C36 C31 2.2(4) . . . . ?
C2 B1 C41 C46 -3.3(3) . . . . ?
C31 B1 C41 C46 119.5(2) . . . . ?
C2 B1 C41 C42 179.41(19) . . . . ?
C31 B1 C41 C42 -57.8(2) . . . . ?
C46 C41 C42 F42 175.89(19) . . . . ?
B1 C41 C42 F42 -6.4(3) . . . . ?
C46 C41 C42 C43 -4.5(3) . . . . ?
B1 C41 C42 C43 173.2(2) . . . . ?
F42 C42 C43 F43 2.6(3) . . . . ?
C41 C42 C43 F43 -177.1(2) . . . . ?
F42 C42 C43 C44 -177.6(2) . . . . ?
C41 C42 C43 C44 2.8(4) . . . . ?
F43 C43 C44 F44 1.5(3) . . . . ?
C42 C43 C44 F44 -178.3(2) . . . . ?
F43 C43 C44 C45 -178.9(2) . . . . ?
C42 C43 C44 C45 1.3(3) . . . . ?
F44 C44 C45 F45 -2.8(3) . . . . ?
C43 C44 C45 F45 177.5(2) . . . . ?
F44 C44 C45 C46 176.4(2) . . . . ?
C43 C44 C45 C46 -3.2(3) . . . . ?
F45 C45 C46 F46 1.1(3) . . . . ?
C44 C45 C46 F46 -178.1(2) . . . . ?
F45 C45 C46 C41 -179.5(2) . . . . ?
C44 C45 C46 C41 1.3(4) . . . . ?
C42 C41 C46 F46 -178.23(19) . . . . ?
B1 C41 C46 F46 4.4(3) . . . . ?
C42 C41 C46 C45 2.4(3) . . . . ?
B1 C41 C46 C45 -175.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        67.44
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.046

# Attachment 'ERK4157B.CIF'

data_erk4157b
_database_code_depnum_ccdc_archive 'CCDC 650366'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H34 B F10 O P'
_chemical_formula_weight         750.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   12.1089(8)
_cell_length_b                   12.7662(10)
_cell_length_c                   12.8752(8)
_cell_angle_alpha                104.669(3)
_cell_angle_beta                 100.577(5)
_cell_angle_gamma                100.279(3)
_cell_volume                     1839.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5261
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    1.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7692
_exptl_absorpt_correction_T_max  0.9340
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20114
_diffrn_reflns_av_R_equivalents  0.078
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.36
_diffrn_reflns_theta_max         67.93
_reflns_number_total             6171
_reflns_number_gt                4081
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1997)'
_computing_cell_refinement       'Collect (Nonius B.V., 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinwoski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0947P)^2^+3.3191P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'at P from difmap, other geom'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6171
_refine_ls_number_parameters     479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2265
_refine_ls_wR_factor_gt          0.1923
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
P1 P -0.10142(10) 0.16743(11) 0.75688(10) 0.0452(3) Uani 1 1 d . . .
H1 H -0.171(3) 0.074(3) 0.761(3) 0.040(11) Uiso 1 1 d . . .
C2 C 0.0044(4) 0.1219(4) 0.6865(4) 0.0453(11) Uani 1 1 d . . .
H2A H -0.0326 0.0824 0.6085 0.054 Uiso 1 1 calc R . .
H2B H 0.0639 0.1866 0.6899 0.054 Uiso 1 1 calc R . .
C3 C 0.0609(4) 0.0432(4) 0.7421(4) 0.0457(11) Uani 1 1 d . . .
H3A H 0.0162 -0.0338 0.7066 0.055 Uiso 1 1 calc R . .
H3B H 0.0588 0.0628 0.8203 0.055 Uiso 1 1 calc R . .
B4 B 0.1954(4) 0.0522(5) 0.7325(4) 0.0420(12) Uani 1 1 d . . .
O5 O 0.1951(2) 0.0400(3) 0.6159(2) 0.0440(7) Uani 1 1 d . . .
C6 C 0.2996(4) 0.0407(4) 0.5834(4) 0.0497(12) Uani 1 1 d . . .
H6A H 0.3164 -0.0329 0.5742 0.060 Uiso 1 1 calc R . .
H6B H 0.3624 0.0951 0.6416 0.060 Uiso 1 1 calc R . .
C11 C -0.2055(4) 0.2333(4) 0.6948(4) 0.0504(12) Uani 1 1 d . . .
C12 C -0.2047(5) 0.2580(5) 0.5949(4) 0.0596(14) Uani 1 1 d . . .
C121 C -0.1113(5) 0.2460(6) 0.5339(5) 0.0759(18) Uani 1 1 d . . .
H12A H -0.0363 0.2760 0.5858 0.114 Uiso 1 1 calc R . .
H12B H -0.1178 0.2865 0.4795 0.114 Uiso 1 1 calc R . .
H12C H -0.1193 0.1678 0.4968 0.114 Uiso 1 1 calc R . .
C13 C -0.2968(5) 0.2982(5) 0.5495(5) 0.0693(16) Uani 1 1 d . . .
H13 H -0.2973 0.3154 0.4826 0.083 Uiso 1 1 calc R . .
C14 C -0.3869(5) 0.3133(5) 0.5994(6) 0.0701(16) Uani 1 1 d . . .
C141 C -0.4826(6) 0.3608(6) 0.5460(7) 0.105(3) Uani 1 1 d . . .
H14A H -0.4740 0.3629 0.4730 0.158 Uiso 1 1 calc R . .
H14B H -0.4769 0.4357 0.5916 0.158 Uiso 1 1 calc R . .
H14C H -0.5575 0.3140 0.5395 0.158 Uiso 1 1 calc R . .
C15 C -0.3850(4) 0.2909(5) 0.6975(5) 0.0660(15) Uani 1 1 d . . .
H15 H -0.4452 0.3030 0.7325 0.079 Uiso 1 1 calc R . .
C16 C -0.2968(4) 0.2504(4) 0.7477(5) 0.0567(13) Uani 1 1 d . . .
C161 C -0.3042(5) 0.2271(5) 0.8550(5) 0.0705(16) Uani 1 1 d . . .
H16A H -0.3712 0.2486 0.8774 0.106 Uiso 1 1 calc R . .
H16B H -0.2348 0.2693 0.9115 0.106 Uiso 1 1 calc R . .
H16C H -0.3115 0.1481 0.8457 0.106 Uiso 1 1 calc R . .
C21 C -0.0261(4) 0.2456(4) 0.8966(4) 0.0450(11) Uani 1 1 d . . .
C22 C 0.0415(4) 0.3546(4) 0.9179(4) 0.0457(11) Uani 1 1 d . . .
C221 C 0.0522(4) 0.4105(4) 0.8295(4) 0.0539(12) Uani 1 1 d . . .
H22A H 0.0969 0.4868 0.8632 0.081 Uiso 1 1 calc R . .
H22B H -0.0242 0.4103 0.7899 0.081 Uiso 1 1 calc R . .
H22C H 0.0908 0.3706 0.7783 0.081 Uiso 1 1 calc R . .
C23 C 0.1033(4) 0.4120(4) 1.0258(4) 0.0568(13) Uani 1 1 d . . .
H23 H 0.1481 0.4847 1.0408 0.068 Uiso 1 1 calc R . .
C24 C 0.1011(4) 0.3653(4) 1.1124(4) 0.0550(13) Uani 1 1 d . . .
C241 C 0.1698(5) 0.4295(5) 1.2293(5) 0.0760(17) Uani 1 1 d . . .
H24A H 0.1174 0.4394 1.2777 0.114 Uiso 1 1 calc R . .
H24B H 0.2124 0.5018 1.2301 0.114 Uiso 1 1 calc R . .
H24C H 0.2236 0.3882 1.2548 0.114 Uiso 1 1 calc R . .
C25 C 0.0360(5) 0.2583(5) 1.0885(4) 0.0557(13) Uani 1 1 d . . .
H25 H 0.0366 0.2252 1.1459 0.067 Uiso 1 1 calc R . .
C26 C -0.0304(4) 0.1971(4) 0.9837(4) 0.0487(12) Uani 1 1 d . . .
C261 C -0.1026(5) 0.0831(4) 0.9701(4) 0.0583(13) Uani 1 1 d . . .
H26A H -0.0807 0.0621 1.0369 0.087 Uiso 1 1 calc R . .
H26B H -0.0898 0.0294 0.9079 0.087 Uiso 1 1 calc R . .
H26C H -0.1837 0.0846 0.9568 0.087 Uiso 1 1 calc R . .
C41 C 0.2651(4) 0.1778(4) 0.8179(4) 0.0408(10) Uani 1 1 d . . .
C42 C 0.2962(4) 0.2737(4) 0.7887(4) 0.0492(12) Uani 1 1 d . . .
F42 F 0.2805(3) 0.2703(2) 0.6801(2) 0.0665(8) Uani 1 1 d . . .
C43 C 0.3419(4) 0.3794(4) 0.8615(5) 0.0583(14) Uani 1 1 d . . .
F43 F 0.3648(3) 0.4685(3) 0.8247(3) 0.0838(10) Uani 1 1 d . . .
C44 C 0.3587(4) 0.3930(4) 0.9723(5) 0.0594(14) Uani 1 1 d . . .
F44 F 0.3983(3) 0.4964(3) 1.0460(3) 0.0837(10) Uani 1 1 d . . .
C45 C 0.3331(4) 0.3005(4) 1.0082(4) 0.0518(12) Uani 1 1 d . . .
F45 F 0.3498(3) 0.3130(3) 1.1178(2) 0.0700(9) Uani 1 1 d . . .
C46 C 0.2858(4) 0.1993(4) 0.9323(4) 0.0437(11) Uani 1 1 d . . .
F46 F 0.2553(2) 0.1135(2) 0.9746(2) 0.0547(7) Uani 1 1 d . . .
C51 C 0.2512(4) -0.0467(4) 0.7736(4) 0.0424(11) Uani 1 1 d . . .
C52 C 0.3670(4) -0.0305(4) 0.8227(4) 0.0480(11) Uani 1 1 d . . .
F52 F 0.4426(2) 0.0674(2) 0.8375(3) 0.0618(8) Uani 1 1 d . . .
C53 C 0.4162(4) -0.1070(5) 0.8609(4) 0.0566(13) Uani 1 1 d . . .
F53 F 0.5296(3) -0.0833(3) 0.9091(3) 0.0754(10) Uani 1 1 d . . .
C54 C 0.3490(5) -0.2081(5) 0.8497(5) 0.0691(16) Uani 1 1 d . . .
F54 F 0.3937(3) -0.2854(3) 0.8870(4) 0.1027(14) Uani 1 1 d . . .
C55 C 0.2332(5) -0.2318(5) 0.7993(5) 0.0655(15) Uani 1 1 d . . .
F55 F 0.1647(3) -0.3328(3) 0.7847(4) 0.1061(14) Uani 1 1 d . . .
C56 C 0.1889(4) -0.1523(4) 0.7623(4) 0.0495(12) Uani 1 1 d . . .
F56 F 0.0737(2) -0.1848(2) 0.7122(3) 0.0626(8) Uani 1 1 d . . .
C61 C 0.2950(4) 0.0699(4) 0.4762(4) 0.0474(11) Uani 1 1 d . . .
C62 C 0.3722(4) 0.0409(5) 0.4130(4) 0.0588(14) Uani 1 1 d . . .
H62 H 0.4219 -0.0029 0.4337 0.071 Uiso 1 1 calc R . .
C63 C 0.3772(5) 0.0752(5) 0.3204(5) 0.0665(16) Uani 1 1 d . . .
H63 H 0.4320 0.0568 0.2802 0.080 Uiso 1 1 calc R . .
C64 C 0.3029(5) 0.1362(5) 0.2866(5) 0.0691(16) Uani 1 1 d . . .
H64 H 0.3064 0.1596 0.2234 0.083 Uiso 1 1 calc R . .
C65 C 0.2227(5) 0.1626(5) 0.3467(5) 0.0613(14) Uani 1 1 d . . .
H65 H 0.1702 0.2028 0.3231 0.074 Uiso 1 1 calc R . .
C66 C 0.2193(4) 0.1303(4) 0.4413(4) 0.0520(12) Uani 1 1 d . . .
H66 H 0.1652 0.1496 0.4821 0.062 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 0.0386(6) 0.0532(7) 0.0465(7) 0.0157(6) 0.0099(5) 0.0169(5)
C2 0.040(2) 0.050(3) 0.046(3) 0.012(2) 0.010(2) 0.016(2)
C3 0.039(2) 0.046(3) 0.057(3) 0.021(2) 0.012(2) 0.015(2)
B4 0.039(3) 0.049(3) 0.039(3) 0.012(2) 0.011(2) 0.013(2)
O5 0.0382(16) 0.056(2) 0.0439(18) 0.0191(15) 0.0142(14) 0.0173(14)
C6 0.048(3) 0.067(3) 0.047(3) 0.025(2) 0.020(2) 0.026(2)
C11 0.048(3) 0.055(3) 0.047(3) 0.015(2) 0.002(2) 0.019(2)
C12 0.061(3) 0.063(3) 0.052(3) 0.010(3) 0.003(3) 0.027(3)
C121 0.091(4) 0.100(5) 0.057(4) 0.041(3) 0.020(3) 0.045(4)
C13 0.076(4) 0.070(4) 0.055(3) 0.017(3) -0.006(3) 0.024(3)
C14 0.051(3) 0.062(4) 0.085(5) 0.011(3) -0.006(3) 0.020(3)
C141 0.072(4) 0.090(5) 0.141(7) 0.033(5) -0.021(4) 0.037(4)
C15 0.043(3) 0.062(4) 0.089(5) 0.018(3) 0.006(3) 0.019(3)
C16 0.039(3) 0.051(3) 0.074(4) 0.009(3) 0.009(2) 0.014(2)
C161 0.057(3) 0.083(4) 0.083(4) 0.029(3) 0.030(3) 0.027(3)
C21 0.039(2) 0.051(3) 0.049(3) 0.017(2) 0.013(2) 0.018(2)
C22 0.041(2) 0.051(3) 0.052(3) 0.020(2) 0.014(2) 0.019(2)
C221 0.055(3) 0.050(3) 0.061(3) 0.020(3) 0.017(3) 0.016(2)
C23 0.054(3) 0.050(3) 0.061(3) 0.007(3) 0.008(3) 0.019(2)
C24 0.057(3) 0.058(3) 0.049(3) 0.010(3) 0.010(2) 0.024(3)
C241 0.084(4) 0.081(4) 0.051(3) 0.005(3) -0.001(3) 0.029(3)
C25 0.066(3) 0.067(4) 0.040(3) 0.020(3) 0.012(2) 0.027(3)
C26 0.050(3) 0.058(3) 0.047(3) 0.020(2) 0.018(2) 0.021(2)
C261 0.065(3) 0.063(3) 0.054(3) 0.027(3) 0.019(3) 0.012(3)
C41 0.034(2) 0.048(3) 0.046(3) 0.016(2) 0.013(2) 0.014(2)
C42 0.046(3) 0.051(3) 0.052(3) 0.016(2) 0.012(2) 0.012(2)
F42 0.085(2) 0.0572(18) 0.060(2) 0.0272(15) 0.0167(16) 0.0096(16)
C43 0.055(3) 0.043(3) 0.077(4) 0.022(3) 0.019(3) 0.005(2)
F43 0.097(3) 0.0498(19) 0.101(3) 0.0255(18) 0.025(2) 0.0026(17)
C44 0.047(3) 0.053(3) 0.063(4) -0.003(3) 0.009(3) 0.005(2)
F44 0.078(2) 0.058(2) 0.088(3) -0.0122(18) 0.0176(19) -0.0003(17)
C45 0.046(3) 0.059(3) 0.044(3) 0.006(2) 0.011(2) 0.009(2)
F45 0.0657(19) 0.084(2) 0.0468(18) 0.0016(15) 0.0086(14) 0.0142(16)
C46 0.040(2) 0.043(3) 0.049(3) 0.015(2) 0.012(2) 0.012(2)
F46 0.0613(17) 0.0605(18) 0.0479(16) 0.0224(14) 0.0155(13) 0.0167(14)
C51 0.040(2) 0.052(3) 0.040(3) 0.015(2) 0.015(2) 0.019(2)
C52 0.050(3) 0.055(3) 0.046(3) 0.017(2) 0.015(2) 0.022(2)
F52 0.0410(15) 0.0648(19) 0.077(2) 0.0188(16) 0.0094(14) 0.0140(14)
C53 0.053(3) 0.075(4) 0.054(3) 0.025(3) 0.018(3) 0.032(3)
F53 0.0590(19) 0.113(3) 0.069(2) 0.0341(19) 0.0129(16) 0.0487(18)
C54 0.079(4) 0.081(4) 0.076(4) 0.043(3) 0.034(3) 0.050(4)
F54 0.111(3) 0.111(3) 0.142(4) 0.088(3) 0.052(3) 0.074(3)
C55 0.067(4) 0.058(3) 0.093(4) 0.040(3) 0.037(3) 0.023(3)
F55 0.095(3) 0.072(2) 0.190(5) 0.075(3) 0.064(3) 0.033(2)
C56 0.043(3) 0.053(3) 0.063(3) 0.025(3) 0.021(2) 0.017(2)
F56 0.0523(17) 0.0500(17) 0.087(2) 0.0217(15) 0.0212(15) 0.0102(13)
C61 0.042(3) 0.061(3) 0.039(3) 0.016(2) 0.007(2) 0.011(2)
C62 0.051(3) 0.085(4) 0.048(3) 0.026(3) 0.015(2) 0.023(3)
C63 0.051(3) 0.098(5) 0.052(3) 0.023(3) 0.021(3) 0.010(3)
C64 0.069(4) 0.084(4) 0.049(3) 0.027(3) 0.008(3) -0.002(3)
C65 0.059(3) 0.063(3) 0.059(3) 0.028(3) 0.002(3) 0.006(3)
C66 0.045(3) 0.068(3) 0.046(3) 0.020(3) 0.010(2) 0.015(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
P1 C21 1.797(5) . ?
P1 C2 1.796(5) . ?
P1 C11 1.812(5) . ?
C2 C3 1.556(6) . ?
C3 B4 1.642(6) . ?
B4 O5 1.469(6) . ?
B4 C41 1.667(7) . ?
B4 C51 1.686(7) . ?
O5 C6 1.403(5) . ?
C6 C61 1.512(6) . ?
C11 C12 1.402(7) . ?
C11 C16 1.421(7) . ?
C12 C13 1.402(7) . ?
C12 C121 1.499(8) . ?
C13 C14 1.382(8) . ?
C14 C15 1.362(8) . ?
C14 C141 1.534(7) . ?
C15 C16 1.392(7) . ?
C16 C161 1.501(8) . ?
C21 C22 1.414(7) . ?
C21 C26 1.416(6) . ?
C22 C23 1.391(7) . ?
C22 C221 1.502(7) . ?
C23 C24 1.393(7) . ?
C24 C25 1.377(7) . ?
C24 C241 1.517(7) . ?
C25 C26 1.386(7) . ?
C26 C261 1.508(7) . ?
C41 C42 1.380(6) . ?
C41 C46 1.393(6) . ?
C42 F42 1.365(6) . ?
C42 C43 1.381(7) . ?
C43 F43 1.343(6) . ?
C43 C44 1.365(8) . ?
C44 F44 1.358(6) . ?
C44 C45 1.379(7) . ?
C45 F45 1.352(6) . ?
C45 C46 1.358(7) . ?
C46 F46 1.366(5) . ?
C51 C56 1.380(7) . ?
C51 C52 1.384(6) . ?
C52 F52 1.358(6) . ?
C52 C53 1.375(7) . ?
C53 F53 1.345(6) . ?
C53 C54 1.355(8) . ?
C54 F54 1.353(6) . ?
C54 C55 1.377(8) . ?
C55 F55 1.350(6) . ?
C55 C56 1.375(7) . ?
C56 F56 1.364(5) . ?
C61 C66 1.383(7) . ?
C61 C62 1.387(7) . ?
C62 C63 1.379(7) . ?
C63 C64 1.372(8) . ?
C64 C65 1.384(8) . ?
C65 C66 1.387(7) . ?

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
C21 P1 C2 107.2(2) . . ?
C21 P1 C11 113.4(2) . . ?
C2 P1 C11 120.5(2) . . ?
C3 C2 P1 109.5(3) . . ?
C2 C3 B4 111.5(4) . . ?
O5 B4 C3 106.8(4) . . ?
O5 B4 C41 114.0(4) . . ?
C3 B4 C41 103.7(4) . . ?
O5 B4 C51 110.2(4) . . ?
C3 B4 C51 112.2(4) . . ?
C41 B4 C51 109.9(4) . . ?
C6 O5 B4 118.8(3) . . ?
O5 C6 C61 111.7(4) . . ?
C12 C11 C16 120.2(4) . . ?
C12 C11 P1 123.2(4) . . ?
C16 C11 P1 116.4(4) . . ?
C13 C12 C11 117.8(5) . . ?
C13 C12 C121 117.6(5) . . ?
C11 C12 C121 124.6(4) . . ?
C14 C13 C12 122.4(6) . . ?
C15 C14 C13 118.9(5) . . ?
C15 C14 C141 121.9(6) . . ?
C13 C14 C141 119.1(6) . . ?
C14 C15 C16 122.1(6) . . ?
C15 C16 C11 118.6(5) . . ?
C15 C16 C161 117.6(5) . . ?
C11 C16 C161 123.8(4) . . ?
C22 C21 C26 120.3(4) . . ?
C22 C21 P1 119.2(4) . . ?
C26 C21 P1 120.4(4) . . ?
C23 C22 C21 118.4(4) . . ?
C23 C22 C221 118.3(5) . . ?
C21 C22 C221 123.3(4) . . ?
C22 C23 C24 122.2(5) . . ?
C25 C24 C23 118.0(5) . . ?
C25 C24 C241 120.8(5) . . ?
C23 C24 C241 121.1(5) . . ?
C24 C25 C26 123.1(5) . . ?
C25 C26 C21 118.0(5) . . ?
C25 C26 C261 117.7(4) . . ?
C21 C26 C261 124.4(4) . . ?
C42 C41 C46 111.7(4) . . ?
C42 C41 B4 126.6(4) . . ?
C46 C41 B4 121.3(4) . . ?
F42 C42 C41 120.6(4) . . ?
F42 C42 C43 113.8(4) . . ?
C41 C42 C43 125.6(5) . . ?
F43 C43 C44 120.0(5) . . ?
F43 C43 C42 121.1(5) . . ?
C44 C43 C42 118.8(5) . . ?
F44 C44 C43 120.4(5) . . ?
F44 C44 C45 120.5(5) . . ?
C43 C44 C45 119.0(5) . . ?
F45 C45 C46 121.3(5) . . ?
F45 C45 C44 119.6(5) . . ?
C46 C45 C44 119.1(5) . . ?
C45 C46 F46 115.4(4) . . ?
C45 C46 C41 125.7(4) . . ?
F46 C46 C41 118.9(4) . . ?
C56 C51 C52 112.0(4) . . ?
C56 C51 B4 125.0(4) . . ?
C52 C51 B4 123.1(4) . . ?
F52 C52 C53 114.3(4) . . ?
F52 C52 C51 120.4(4) . . ?
C53 C52 C51 125.3(5) . . ?
F53 C53 C54 119.3(5) . . ?
F53 C53 C52 121.3(5) . . ?
C54 C53 C52 119.4(5) . . ?
F54 C54 C53 121.3(5) . . ?
F54 C54 C55 119.8(6) . . ?
C53 C54 C55 118.9(5) . . ?
F55 C55 C56 120.7(5) . . ?
F55 C55 C54 120.2(5) . . ?
C56 C55 C54 119.2(5) . . ?
F56 C56 C55 114.4(4) . . ?
F56 C56 C51 120.4(4) . . ?
C55 C56 C51 125.2(5) . . ?
C66 C61 C62 118.3(4) . . ?
C66 C61 C6 121.8(4) . . ?
C62 C61 C6 119.8(4) . . ?
C63 C62 C61 121.1(5) . . ?
C64 C63 C62 120.5(5) . . ?
C63 C64 C65 119.1(5) . . ?
C64 C65 C66 120.5(5) . . ?
C61 C66 C65 120.5(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
C21 P1 C2 C3 62.6(4) . . . . ?
C11 P1 C2 C3 -165.8(3) . . . . ?
P1 C2 C3 B4 -149.3(3) . . . . ?
C2 C3 B4 O5 -50.0(5) . . . . ?
C2 C3 B4 C41 70.7(5) . . . . ?
C2 C3 B4 C51 -170.8(4) . . . . ?
C3 B4 O5 C6 -177.9(4) . . . . ?
C41 B4 O5 C6 68.2(5) . . . . ?
C51 B4 O5 C6 -55.8(5) . . . . ?
B4 O5 C6 C61 -159.0(4) . . . . ?
C21 P1 C11 C12 124.8(4) . . . . ?
C2 P1 C11 C12 -4.1(6) . . . . ?
C21 P1 C11 C16 -60.8(5) . . . . ?
C2 P1 C11 C16 170.4(4) . . . . ?
C16 C11 C12 C13 -0.9(8) . . . . ?
P1 C11 C12 C13 173.4(4) . . . . ?
C16 C11 C12 C121 178.3(5) . . . . ?
P1 C11 C12 C121 -7.4(8) . . . . ?
C11 C12 C13 C14 -0.2(9) . . . . ?
C121 C12 C13 C14 -179.5(6) . . . . ?
C12 C13 C14 C15 1.5(9) . . . . ?
C12 C13 C14 C141 178.2(6) . . . . ?
C13 C14 C15 C16 -1.7(9) . . . . ?
C141 C14 C15 C16 -178.3(5) . . . . ?
C14 C15 C16 C11 0.6(8) . . . . ?
C14 C15 C16 C161 -179.2(5) . . . . ?
C12 C11 C16 C15 0.7(8) . . . . ?
P1 C11 C16 C15 -174.0(4) . . . . ?
C12 C11 C16 C161 -179.5(5) . . . . ?
P1 C11 C16 C161 5.8(7) . . . . ?
C2 P1 C21 C22 74.8(4) . . . . ?
C11 P1 C21 C22 -60.5(4) . . . . ?
C2 P1 C21 C26 -102.5(4) . . . . ?
C11 P1 C21 C26 122.1(4) . . . . ?
C26 C21 C22 C23 0.2(6) . . . . ?
P1 C21 C22 C23 -177.1(3) . . . . ?
C26 C21 C22 C221 178.6(4) . . . . ?
P1 C21 C22 C221 1.3(6) . . . . ?
C21 C22 C23 C24 0.4(7) . . . . ?
C221 C22 C23 C24 -178.1(4) . . . . ?
C22 C23 C24 C25 0.7(7) . . . . ?
C22 C23 C24 C241 179.7(5) . . . . ?
C23 C24 C25 C26 -2.5(8) . . . . ?
C241 C24 C25 C26 178.5(5) . . . . ?
C24 C25 C26 C21 3.1(7) . . . . ?
C24 C25 C26 C261 -176.8(5) . . . . ?
C22 C21 C26 C25 -1.9(6) . . . . ?
P1 C21 C26 C25 175.4(4) . . . . ?
C22 C21 C26 C261 178.0(4) . . . . ?
P1 C21 C26 C261 -4.7(6) . . . . ?
O5 B4 C41 C42 16.3(6) . . . . ?
C3 B4 C41 C42 -99.3(5) . . . . ?
C51 B4 C41 C42 140.6(4) . . . . ?
O5 B4 C41 C46 -172.1(4) . . . . ?
C3 B4 C41 C46 72.2(5) . . . . ?
C51 B4 C41 C46 -47.9(5) . . . . ?
C46 C41 C42 F42 -178.7(4) . . . . ?
B4 C41 C42 F42 -6.4(7) . . . . ?
C46 C41 C42 C43 -0.2(7) . . . . ?
B4 C41 C42 C43 172.0(5) . . . . ?
F42 C42 C43 F43 1.4(7) . . . . ?
C41 C42 C43 F43 -177.1(4) . . . . ?
F42 C42 C43 C44 178.4(4) . . . . ?
C41 C42 C43 C44 -0.1(8) . . . . ?
F43 C43 C44 F44 0.2(8) . . . . ?
C42 C43 C44 F44 -176.9(4) . . . . ?
F43 C43 C44 C45 179.1(5) . . . . ?
C42 C43 C44 C45 2.1(8) . . . . ?
F44 C44 C45 F45 -1.3(7) . . . . ?
C43 C44 C45 F45 179.7(4) . . . . ?
F44 C44 C45 C46 175.3(4) . . . . ?
C43 C44 C45 C46 -3.7(7) . . . . ?
F45 C45 C46 F46 1.1(6) . . . . ?
C44 C45 C46 F46 -175.4(4) . . . . ?
F45 C45 C46 C41 -179.9(4) . . . . ?
C44 C45 C46 C41 3.6(7) . . . . ?
C42 C41 C46 C45 -1.6(6) . . . . ?
B4 C41 C46 C45 -174.3(4) . . . . ?
C42 C41 C46 F46 177.4(4) . . . . ?
B4 C41 C46 F46 4.7(6) . . . . ?
O5 B4 C51 C56 -86.9(5) . . . . ?
C3 B4 C51 C56 31.9(6) . . . . ?
C41 B4 C51 C56 146.7(4) . . . . ?
O5 B4 C51 C52 92.6(5) . . . . ?
C3 B4 C51 C52 -148.5(4) . . . . ?
C41 B4 C51 C52 -33.7(6) . . . . ?
C56 C51 C52 F52 177.9(4) . . . . ?
B4 C51 C52 F52 -1.7(7) . . . . ?
C56 C51 C52 C53 -2.5(7) . . . . ?
B4 C51 C52 C53 177.9(5) . . . . ?
F52 C52 C53 F53 0.6(7) . . . . ?
C51 C52 C53 F53 -179.0(4) . . . . ?
F52 C52 C53 C54 -179.5(5) . . . . ?
C51 C52 C53 C54 1.0(8) . . . . ?
F53 C53 C54 F54 0.6(8) . . . . ?
C52 C53 C54 F54 -179.4(5) . . . . ?
F53 C53 C54 C55 -179.4(5) . . . . ?
C52 C53 C54 C55 0.6(8) . . . . ?
F54 C54 C55 F55 -1.6(9) . . . . ?
C53 C54 C55 F55 178.5(5) . . . . ?
F54 C54 C55 C56 179.6(5) . . . . ?
C53 C54 C55 C56 -0.3(9) . . . . ?
F55 C55 C56 F56 0.3(8) . . . . ?
C54 C55 C56 F56 179.0(5) . . . . ?
F55 C55 C56 C51 179.7(5) . . . . ?
C54 C55 C56 C51 -1.6(9) . . . . ?
C52 C51 C56 F56 -177.8(4) . . . . ?
B4 C51 C56 F56 1.8(7) . . . . ?
C52 C51 C56 C55 2.8(7) . . . . ?
B4 C51 C56 C55 -177.6(5) . . . . ?
O5 C6 C61 C66 24.1(7) . . . . ?
O5 C6 C61 C62 -159.3(5) . . . . ?
C66 C61 C62 C63 2.8(8) . . . . ?
C6 C61 C62 C63 -174.0(5) . . . . ?
C61 C62 C63 C64 -2.1(9) . . . . ?
C62 C63 C64 C65 -0.1(9) . . . . ?
C63 C64 C65 C66 1.5(9) . . . . ?
C62 C61 C66 C65 -1.3(8) . . . . ?
C6 C61 C66 C65 175.4(5) . . . . ?
C64 C65 C66 C61 -0.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.921
_diffrn_reflns_theta_full        67.93
_diffrn_measured_fraction_theta_full 0.921
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.077