# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2003

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Armin Borner'
'Jens Holz'
'Igor V. Komarov'
'Anke Spannenberg'

_publ_contact_author_name        'Prof Armin Borner'
_publ_contact_author_address     
;
IfOK
Buchbinderstr. 5-6
Rostock
18055
GERMANY
;

_publ_contact_author_email       ARMIN.BOERNER@IFOK.UNI-ROSTOCK.DE

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Highly stereoselective, thermodynamically
controlled and reversible formation of a new P-chiral phosphine 
;
#-------------------------------------------------------------------------

data_KS015
_database_code_CSD               202862

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
? 
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C16 H21 O P'
_chemical_formula_weight         260.30
_chemical_melting_point          ?
_chemical_compound_source        ?

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.7590(10)
_cell_length_b                   9.998(2)
_cell_length_c                   21.043(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1422.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2000
_cell_measurement_theta_min      4
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   no
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
; 
? 
;

_diffrn_ambient_temperature      293(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       STOE-IPDS
_diffrn_measurement_method       'laser scanned imaging plate'
_diffrn_standards_number         50-200
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  360
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5231
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         21.08
_reflns_number_total             1494
_reflns_number_observed          1230
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       STOE-EXPOSE
_computing_cell_refinement       STOE-CELL
_computing_data_reduction        STOE-INTEGRATE
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    XP
_computing_publication_material  SHELXL-93

_refine_special_details          
; 
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
or flagged by the user for potential systematic errors.  Weighted R-factors 
wR and all goodnesses 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 observed criterion 
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.0000P] 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    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(19)
_refine_ls_number_reflns         1494
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_obs          0.0336
_refine_ls_wR_factor_all         0.0786
_refine_ls_wR_factor_obs         0.0755
_refine_ls_goodness_of_fit_all   0.931
_refine_ls_goodness_of_fit_obs   0.999
_refine_ls_restrained_S_all      0.931
_refine_ls_restrained_S_obs      0.999
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
C1 C 0.5611(5) 0.1967(3) 0.1910(2) 0.0414(9) Uani 1 d . .
H1A H 0.5235(5) 0.1090(3) 0.1754(2) 0.050 Uiso 1 calc R .
H1B H 0.4443(5) 0.2407(3) 0.2077(2) 0.050 Uiso 1 calc R .
C2 C 0.6538(6) 0.2810(3) 0.1370(2) 0.0410(10) Uani 1 d . .
C3 C 0.8806(6) 0.2785(3) 0.1430(2) 0.0408(10) Uani 1 d . .
C4 C 0.8841(5) 0.3228(3) 0.2139(2) 0.0379(9) Uani 1 d . .
C5 C 0.7497(6) 0.4472(3) 0.21323(15) 0.0421(8) Uani 1 d . .
H5A H 0.6591(6) 0.4468(3) 0.24900(15) 0.050 Uiso 1 calc R .
H5B H 0.8271(6) 0.5289(3) 0.21425(15) 0.050 Uiso 1 calc R .
C6 C 0.6378(7) 0.4332(4) 0.1500(2) 0.0447(10) Uani 1 d . .
H6 H 0.5125(53) 0.4740(30) 0.1480(15) 0.037(10) Uiso 1 d . .
C7 C 0.7753(7) 0.4921(3) 0.0993(2) 0.0589(11) Uani 1 d . .
H7A H 0.7127(7) 0.4928(3) 0.0579(2) 0.071 Uiso 1 calc R .
H7B H 0.8160(7) 0.5822(3) 0.1103(2) 0.071 Uiso 1 calc R .
C8 C 0.9494(6) 0.3955(4) 0.1011(2) 0.0576(12) Uani 1 d . .
H8A H 1.0652(6) 0.4382(4) 0.1192(2) 0.069 Uiso 1 calc R .
H8B H 0.9816(6) 0.3646(4) 0.0586(2) 0.069 Uiso 1 calc R .
C9 C 0.6571(6) 0.2571(3) 0.3263(2) 0.0420(10) Uani 1 d . .
C10 C 0.4643(6) 0.2895(3) 0.3391(2) 0.0498(11) Uani 1 d . .
H10 H 0.3689(6) 0.2769(3) 0.3078(2) 0.060 Uiso 1 calc R .
C11 C 0.4078(7) 0.3408(4) 0.3977(2) 0.0608(11) Uani 1 d . .
H11 H 0.2759(7) 0.3621(4) 0.4054(2) 0.073 Uiso 1 calc R .
C12 C 0.5476(8) 0.3602(4) 0.4445(2) 0.0637(13) Uani 1 d . .
H12 H 0.5106(8) 0.3941(4) 0.4839(2) 0.076 Uiso 1 calc R .
C13 C 0.7411(9) 0.3290(4) 0.4326(2) 0.0753(13) Uani 1 d . .
H13 H 0.8364(9) 0.3430(4) 0.4638(2) 0.090 Uiso 1 calc R .
C14 C 0.7954(6) 0.2770(4) 0.3746(2) 0.0626(13) Uani 1 d . .
H14 H 0.9271(6) 0.2547(4) 0.3674(2) 0.075 Uiso 1 calc R .
C15 C 0.5694(6) 0.2383(4) 0.0725(2) 0.0657(13) Uani 1 d . .
H15A H 0.4276(6) 0.2433(4) 0.0737(2) 0.099 Uiso 1 calc R .
H15B H 0.6091(6) 0.1481(4) 0.0634(2) 0.099 Uiso 1 calc R .
H15C H 0.6186(6) 0.2967(4) 0.0399(2) 0.099 Uiso 1 calc R .
C16 C 0.9865(5) 0.1480(3) 0.1288(2) 0.0563(12) Uani 1 d . .
H16A H 0.9371(5) 0.0793(3) 0.1564(2) 0.084 Uiso 1 calc R .
H16B H 1.1259(5) 0.1592(3) 0.1357(2) 0.084 Uiso 1 calc R .
H16C H 0.9634(5) 0.1231(3) 0.0854(2) 0.084 Uiso 1 calc R .
O O 1.0751(4) 0.3433(2) 0.24083(13) 0.0561(7) Uani 1 d . .
H0 H 1.1084(27) 0.4214(11) 0.2357(18) 0.084 Uiso 1 calc R .
P P 0.7531(2) 0.18143(8) 0.25356(4) 0.0419(3) Uani 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
C1 0.042(2) 0.037(2) 0.045(2) -0.004(2) -0.003(2) -0.002(2)
C2 0.049(3) 0.041(2) 0.033(2) -0.003(2) 0.000(2) -0.004(2)
C3 0.038(3) 0.037(2) 0.047(2) -0.002(2) 0.008(2) 0.002(2)
C4 0.030(2) 0.037(2) 0.046(2) -0.007(2) -0.005(2) 0.005(2)
C5 0.045(2) 0.037(2) 0.044(2) -0.0008(15) 0.002(2) -0.005(2)
C6 0.047(3) 0.043(2) 0.044(2) 0.004(2) -0.001(2) 0.006(2)
C7 0.077(3) 0.047(2) 0.052(2) 0.006(2) 0.004(2) -0.001(3)
C8 0.066(3) 0.055(3) 0.052(3) -0.002(2) 0.010(2) -0.010(2)
C9 0.054(3) 0.031(2) 0.042(2) 0.002(2) -0.005(2) 0.003(2)
C10 0.054(3) 0.050(3) 0.046(3) 0.001(2) -0.005(2) 0.000(2)
C11 0.064(3) 0.060(3) 0.058(3) -0.005(2) 0.017(2) -0.001(2)
C12 0.095(4) 0.061(3) 0.036(3) -0.007(2) 0.007(3) 0.003(3)
C13 0.094(4) 0.086(3) 0.046(3) -0.009(2) -0.020(3) 0.016(4)
C14 0.056(3) 0.077(3) 0.054(3) -0.009(2) -0.013(2) 0.014(2)
C15 0.078(4) 0.078(3) 0.041(2) -0.004(2) -0.007(2) -0.015(3)
C16 0.054(3) 0.054(2) 0.061(3) -0.013(2) 0.012(2) 0.006(2)
O 0.042(2) 0.056(2) 0.070(2) -0.001(2) -0.0085(14) -0.0026(12)
P 0.0474(6) 0.0363(4) 0.0421(5) 0.0005(4) -0.0025(6) 0.0034(5)

_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
C1 C2 1.547(5) . ?
C1 P 1.855(3) . ?
C2 C15 1.533(5) . ?
C2 C3 1.538(5) . ?
C2 C6 1.550(5) . ?
C3 C16 1.517(5) . ?
C3 C8 1.537(5) . ?
C3 C4 1.557(5) . ?
C4 O 1.424(4) . ?
C4 C5 1.540(5) . ?
C4 P 1.865(3) . ?
C5 C6 1.537(5) . ?
C6 C7 1.531(5) . ?
C7 C8 1.522(5) . ?
C9 C10 1.370(5) . ?
C9 C14 1.395(5) . ?
C9 P 1.827(3) . ?
C10 C11 1.389(5) . ?
C11 C12 1.379(5) . ?
C12 C13 1.368(6) . ?
C13 C14 1.376(5) . ?

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
C2 C1 P 106.4(2) . . ?
C15 C2 C3 116.0(3) . . ?
C15 C2 C1 110.4(3) . . ?
C3 C2 C1 109.6(3) . . ?
C15 C2 C6 113.8(3) . . ?
C3 C2 C6 94.1(3) . . ?
C1 C2 C6 112.2(3) . . ?
C16 C3 C8 113.5(3) . . ?
C16 C3 C2 117.9(3) . . ?
C8 C3 C2 104.0(3) . . ?
C16 C3 C4 115.2(3) . . ?
C8 C3 C4 109.2(3) . . ?
C2 C3 C4 95.1(3) . . ?
O C4 C5 115.0(3) . . ?
O C4 C3 115.9(3) . . ?
C5 C4 C3 102.2(3) . . ?
O C4 P 111.1(2) . . ?
C5 C4 P 109.6(2) . . ?
C3 C4 P 101.9(2) . . ?
C6 C5 C4 103.0(3) . . ?
C7 C6 C5 105.6(3) . . ?
C7 C6 C2 102.3(3) . . ?
C5 C6 C2 102.0(3) . . ?
C8 C7 C6 102.0(3) . . ?
C7 C8 C3 105.2(3) . . ?
C10 C9 C14 117.4(3) . . ?
C10 C9 P 126.9(3) . . ?
C14 C9 P 115.6(3) . . ?
C9 C10 C11 121.6(4) . . ?
C12 C11 C10 119.9(4) . . ?
C13 C12 C11 119.5(4) . . ?
C12 C13 C14 120.3(4) . . ?
C13 C14 C9 121.4(4) . . ?
C9 P C1 108.2(2) . . ?
C9 P C4 103.3(2) . . ?
C1 P C4 87.3(2) . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036