# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'Maryse Gouygou'
_publ_contact_author_email       MARYSEGOUYGOU@LCC-TOULOUSE.FR

_publ_section_title              
;
Chiral diphosphinites derived from 2,2-biphosphole
as a new class of stereodynamic ligands for enantioselective
hydrogenation
;
loop_
_publ_author_name
'Maryse Gouygou'
'Jozsef Bakos'
'Jean-Claude Daran'
'Csaba Hegedus'
'Emmanuel Robe'

data_3a
_database_code_depnum_ccdc_archive 'CCDC 613282'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 O2 P2'
_chemical_formula_sum            'C28 H30 O2 P2'
_chemical_compound_source        'synthesis as described'
_chemical_formula_weight         460.46
_chemical_absolute_configuration ad

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   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   9.4358(8)
_cell_length_b                   11.4428(10)
_cell_length_c                   23.1598(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2500.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4811
_cell_measurement_theta_max      32.2
_cell_measurement_theta_min      2.8

_exptl_crystal_description       flattened
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.984

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      180(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  'Oxford-Diffraction XCALIBUR'
_diffrn_measurement_method       '\w and \f'
_diffrn_detector_area_resol_mean 8.2632
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17138
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         24.96
_reflns_number_total             4417
_reflns_number_gt                3672
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       
;
CrysAlis CCD, Version 1.170.32 (Oxford Diffraction, 2003)
;
_computing_cell_refinement       
;
CrysAlis RED, Version 1.170.32 (Oxford Diffraction, 2003)

;
_computing_data_reduction        'CrysAlis RED'
_computing_structure_solution    'SIR-97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0857P)^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    constr
_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   0.06(14)
_refine_ls_number_reflns         4417
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.42655(11) 1.07148(9) 0.37940(5) 0.0429(3) Uani 1 1 d . . .
P2 P 0.40316(10) 0.95439(8) 0.55486(4) 0.0338(2) Uani 1 1 d . . .
O1 O 0.5790(3) 1.0073(2) 0.38842(11) 0.0441(7) Uani 1 1 d . . .
O2 O 0.5263(3) 0.8691(2) 0.52905(12) 0.0404(7) Uani 1 1 d . . .
C1 C 0.5857(4) 0.8837(4) 0.40227(18) 0.0462(10) Uani 1 1 d . . .
H1A H 0.6130 0.8390 0.3674 0.055 Uiso 1 1 calc R . .
H1B H 0.4910 0.8563 0.4148 0.055 Uiso 1 1 calc R . .
C2 C 0.6596(4) 0.9158(4) 0.50779(17) 0.0436(10) Uani 1 1 d . . .
H2 H 0.6523 1.0026 0.5038 0.052 Uiso 1 1 calc R . .
C3 C 0.6915(4) 0.8615(4) 0.44945(18) 0.0475(10) Uani 1 1 d . . .
H3A H 0.7849 0.8907 0.4363 0.057 Uiso 1 1 calc R . .
H3B H 0.7002 0.7759 0.4547 0.057 Uiso 1 1 calc R . .
C4 C 0.7731(4) 0.8854(4) 0.5518(2) 0.0580(12) Uani 1 1 d . . .
H4A H 0.7470 0.9179 0.5894 0.087 Uiso 1 1 calc R . .
H4B H 0.8640 0.9184 0.5394 0.087 Uiso 1 1 calc R . .
H4C H 0.7815 0.8002 0.5548 0.087 Uiso 1 1 calc R . .
C11 C 0.3226(4) 1.0301(3) 0.44209(16) 0.0353(8) Uani 1 1 d . . .
C12 C 0.2083(4) 0.9662(3) 0.42533(16) 0.0365(9) Uani 1 1 d . . .
C13 C 0.2060(4) 0.9392(3) 0.36338(17) 0.0394(9) Uani 1 1 d . . .
C14 C 0.3193(4) 0.9785(3) 0.33334(17) 0.0407(9) Uani 1 1 d . . .
C21 C 0.3685(3) 1.0630(3) 0.50013(15) 0.0328(8) Uani 1 1 d . . .
C22 C 0.3903(4) 1.1712(3) 0.52228(17) 0.0417(9) Uani 1 1 d . . .
C23 C 0.4518(4) 1.1719(3) 0.57969(17) 0.0396(9) Uani 1 1 d . . .
C24 C 0.4841(4) 1.0651(3) 0.60130(16) 0.0368(9) Uani 1 1 d . . .
C121 C 0.0909(4) 0.9319(3) 0.46421(17) 0.0423(9) Uani 1 1 d . . .
H12A H 0.1177 0.9480 0.5043 0.064 Uiso 1 1 calc R . .
H12B H 0.0715 0.8483 0.4597 0.064 Uiso 1 1 calc R . .
H12C H 0.0058 0.9768 0.4544 0.064 Uiso 1 1 calc R . .
C131 C 0.0800(4) 0.8738(4) 0.33804(19) 0.0511(11) Uani 1 1 d . . .
H13A H 0.0857 0.8754 0.2958 0.077 Uiso 1 1 calc R . .
H13B H -0.0081 0.9114 0.3505 0.077 Uiso 1 1 calc R . .
H13C H 0.0814 0.7926 0.3515 0.077 Uiso 1 1 calc R . .
C141 C 0.3504(4) 0.9645(4) 0.27088(17) 0.0453(10) Uani 1 1 d . . .
C142 C 0.3947(5) 1.0599(5) 0.2377(2) 0.0620(12) Uani 1 1 d . . .
H142 H 0.4059 1.1344 0.2553 0.074 Uiso 1 1 calc R . .
C143 C 0.4227(6) 1.0460(6) 0.1788(2) 0.0790(16) Uani 1 1 d . . .
H143 H 0.4538 1.1111 0.1567 0.095 Uiso 1 1 calc R . .
C144 C 0.4061(6) 0.9406(7) 0.1528(2) 0.0818(18) Uani 1 1 d . . .
H144 H 0.4212 0.9328 0.1124 0.098 Uiso 1 1 calc R . .
C145 C 0.3672(5) 0.8454(6) 0.1852(2) 0.0754(16) Uani 1 1 d . . .
H145 H 0.3604 0.7707 0.1676 0.091 Uiso 1 1 calc R . .
C146 C 0.3378(5) 0.8577(5) 0.2437(2) 0.0597(13) Uani 1 1 d . . .
H146 H 0.3085 0.7914 0.2654 0.072 Uiso 1 1 calc R . .
C221 C 0.3473(6) 1.2832(3) 0.4925(2) 0.0648(14) Uani 1 1 d . . .
H22A H 0.3008 1.2647 0.4558 0.097 Uiso 1 1 calc R . .
H22B H 0.4317 1.3309 0.4851 0.097 Uiso 1 1 calc R . .
H22C H 0.2816 1.3267 0.5172 0.097 Uiso 1 1 calc R . .
C231 C 0.4706(6) 1.2865(4) 0.6120(2) 0.0613(13) Uani 1 1 d . . .
H23A H 0.4889 1.2704 0.6529 0.092 Uiso 1 1 calc R . .
H23B H 0.3842 1.3335 0.6084 0.092 Uiso 1 1 calc R . .
H23C H 0.5508 1.3297 0.5956 0.092 Uiso 1 1 calc R . .
C241 C 0.5509(4) 1.0349(4) 0.65686(15) 0.0400(9) Uani 1 1 d . . .
C242 C 0.4985(5) 0.9439(4) 0.68983(17) 0.0495(11) Uani 1 1 d . . .
H242 H 0.4149 0.9038 0.6784 0.059 Uiso 1 1 calc R . .
C243 C 0.5695(6) 0.9121(4) 0.7399(2) 0.0704(15) Uani 1 1 d . . .
H243 H 0.5343 0.8484 0.7619 0.084 Uiso 1 1 calc R . .
C244 C 0.6882(6) 0.9691(5) 0.7586(2) 0.0706(14) Uani 1 1 d . . .
H244 H 0.7339 0.9461 0.7933 0.085 Uiso 1 1 calc R . .
C245 C 0.7407(5) 1.0608(5) 0.7260(2) 0.0659(14) Uani 1 1 d . . .
H245 H 0.8226 1.1021 0.7384 0.079 Uiso 1 1 calc R . .
C246 C 0.6730(5) 1.0923(4) 0.67504(19) 0.0549(11) Uani 1 1 d . . .
H246 H 0.7106 1.1540 0.6523 0.066 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 0.0438(6) 0.0417(6) 0.0431(6) 0.0045(5) 0.0001(5) -0.0106(5)
P2 0.0318(4) 0.0279(5) 0.0418(5) 0.0022(4) 0.0061(4) -0.0017(4)
O1 0.0360(14) 0.0485(16) 0.0478(16) 0.0023(12) 0.0030(12) -0.0110(12)
O2 0.0317(13) 0.0303(14) 0.0593(18) 0.0042(12) 0.0093(12) 0.0022(11)
C1 0.032(2) 0.054(2) 0.053(2) -0.0063(19) 0.0069(18) -0.0045(19)
C2 0.0289(19) 0.048(2) 0.054(3) 0.001(2) 0.0070(17) -0.0085(17)
C3 0.031(2) 0.053(2) 0.058(3) -0.003(2) 0.0057(19) 0.0026(18)
C4 0.039(2) 0.068(3) 0.067(3) 0.002(2) 0.005(2) 0.001(2)
C11 0.0321(18) 0.0278(18) 0.046(2) 0.0003(17) 0.0002(16) 0.0016(15)
C12 0.0314(18) 0.0249(18) 0.053(2) 0.0017(17) -0.0017(16) 0.0033(16)
C13 0.0346(19) 0.037(2) 0.047(2) 0.0003(17) -0.0059(17) -0.0013(17)
C14 0.043(2) 0.034(2) 0.045(2) 0.0017(18) -0.0012(18) -0.0005(17)
C21 0.0292(18) 0.0276(18) 0.042(2) -0.0005(16) 0.0056(15) 0.0015(15)
C22 0.050(2) 0.031(2) 0.044(2) 0.0023(16) -0.0015(19) -0.0034(18)
C23 0.046(2) 0.0298(19) 0.043(2) -0.0068(17) 0.0063(18) -0.0042(17)
C24 0.0356(19) 0.036(2) 0.038(2) 0.0038(17) 0.0035(15) -0.0074(17)
C121 0.0307(18) 0.042(2) 0.054(2) 0.0011(18) 0.0020(17) 0.0040(19)
C131 0.039(2) 0.058(3) 0.056(3) -0.001(2) -0.007(2) -0.004(2)
C141 0.039(2) 0.058(3) 0.039(2) 0.004(2) -0.0071(17) 0.003(2)
C142 0.058(3) 0.075(3) 0.053(3) 0.007(2) -0.001(2) 0.005(3)
C143 0.073(3) 0.110(5) 0.054(3) 0.025(3) 0.010(3) 0.020(4)
C144 0.064(3) 0.135(6) 0.046(3) -0.005(4) 0.001(2) 0.022(4)
C145 0.052(3) 0.117(5) 0.058(3) -0.024(3) -0.005(2) 0.013(3)
C146 0.046(3) 0.074(3) 0.059(3) -0.007(2) -0.004(2) 0.003(2)
C221 0.095(4) 0.026(2) 0.073(3) 0.000(2) -0.017(3) 0.009(2)
C231 0.095(3) 0.036(2) 0.053(3) -0.007(2) -0.007(3) -0.003(2)
C241 0.045(2) 0.042(2) 0.033(2) -0.0022(17) 0.0044(16) 0.0020(19)
C242 0.064(3) 0.046(2) 0.038(2) 0.004(2) 0.0067(19) 0.008(2)
C243 0.102(4) 0.060(3) 0.050(3) 0.010(2) 0.012(3) 0.015(3)
C244 0.079(4) 0.087(4) 0.046(3) 0.000(3) -0.006(3) 0.022(3)
C245 0.051(3) 0.100(4) 0.047(3) -0.019(3) -0.005(2) 0.014(3)
C246 0.052(3) 0.072(3) 0.041(2) -0.002(2) 0.002(2) -0.010(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 O1 1.629(3) . ?
P1 C14 1.815(4) . ?
P1 C11 1.815(4) . ?
P2 O2 1.631(3) . ?
P2 C21 1.805(4) . ?
P2 C24 1.829(4) . ?
O1 C1 1.451(5) . ?
O2 C2 1.452(4) . ?
C1 C3 1.502(6) . ?
C2 C4 1.518(6) . ?
C2 C3 1.517(6) . ?
C11 C12 1.360(5) . ?
C11 C21 1.462(5) . ?
C12 C13 1.468(5) . ?
C12 C121 1.481(5) . ?
C13 C14 1.352(5) . ?
C13 C131 1.522(5) . ?
C14 C141 1.485(6) . ?
C21 C22 1.355(5) . ?
C22 C23 1.451(6) . ?
C22 C221 1.512(5) . ?
C23 C24 1.356(5) . ?
C23 C231 1.521(5) . ?
C24 C241 1.474(5) . ?
C141 C146 1.380(6) . ?
C141 C142 1.398(6) . ?
C142 C143 1.400(7) . ?
C143 C144 1.356(9) . ?
C144 C145 1.373(8) . ?
C145 C146 1.390(7) . ?
C241 C242 1.383(6) . ?
C241 C246 1.391(6) . ?
C242 C243 1.388(7) . ?
C243 C244 1.367(7) . ?
C244 C245 1.385(8) . ?
C245 C246 1.389(6) . ?

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
O1 P1 C14 107.66(16) . . ?
O1 P1 C11 104.88(15) . . ?
C14 P1 C11 90.92(17) . . ?
O2 P2 C21 106.48(15) . . ?
O2 P2 C24 109.42(16) . . ?
C21 P2 C24 90.67(17) . . ?
C1 O1 P1 120.4(2) . . ?
C2 O2 P2 121.4(2) . . ?
O1 C1 C3 110.8(3) . . ?
O2 C2 C4 107.4(3) . . ?
O2 C2 C3 108.9(3) . . ?
C4 C2 C3 111.3(3) . . ?
C1 C3 C2 116.5(3) . . ?
C12 C11 C21 129.5(3) . . ?
C12 C11 P1 109.9(3) . . ?
C21 C11 P1 120.6(3) . . ?
C11 C12 C13 113.8(3) . . ?
C11 C12 C121 124.2(3) . . ?
C13 C12 C121 121.8(3) . . ?
C14 C13 C12 114.9(3) . . ?
C14 C13 C131 125.6(4) . . ?
C12 C13 C131 119.5(3) . . ?
C13 C14 C141 128.4(4) . . ?
C13 C14 P1 109.5(3) . . ?
C141 C14 P1 121.7(3) . . ?
C22 C21 C11 128.9(3) . . ?
C22 C21 P2 109.6(3) . . ?
C11 C21 P2 121.5(3) . . ?
C21 C22 C23 114.4(3) . . ?
C21 C22 C221 124.1(4) . . ?
C23 C22 C221 121.4(3) . . ?
C24 C23 C22 115.0(3) . . ?
C24 C23 C231 124.8(4) . . ?
C22 C23 C231 120.2(3) . . ?
C23 C24 C241 129.0(3) . . ?
C23 C24 P2 108.3(3) . . ?
C241 C24 P2 122.0(3) . . ?
C146 C141 C142 117.8(4) . . ?
C146 C141 C14 121.5(4) . . ?
C142 C141 C14 120.7(4) . . ?
C143 C142 C141 120.2(5) . . ?
C144 C143 C142 120.8(6) . . ?
C143 C144 C145 119.6(5) . . ?
C144 C145 C146 120.4(6) . . ?
C141 C146 C145 121.1(5) . . ?
C242 C241 C246 119.0(4) . . ?
C242 C241 C24 120.4(4) . . ?
C246 C241 C24 120.5(4) . . ?
C241 C242 C243 119.1(4) . . ?
C244 C243 C242 122.4(5) . . ?
C243 C244 C245 118.8(5) . . ?
C244 C245 C246 119.7(5) . . ?
C245 C246 C241 121.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.96
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.052

#====END
#=====================================================
data_3b
_database_code_depnum_ccdc_archive 'CCDC 613283'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H32 O2 P2'
_chemical_formula_sum            'C29 H32 O2 P2'
_chemical_compound_source        'synthesis as described'
_chemical_formula_weight         474.49
_chemical_absolute_configuration ad

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   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   9.4289(7)
_cell_length_b                   11.4294(12)
_cell_length_c                   23.7723(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2561.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      26.1

_exptl_crystal_description       box
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.8893
_exptl_absorpt_correction_T_max  0.9477

_exptl_special_details           
;
The data were collected on a Stoe Imaging Plate Diffraction
System (IPDS). The crystal-to-detector distance was 70 mm. 135 frames
(2 min per frame) were obtained with 0 < \f < 250.5\% and with the crystals
rotated through 1.5\% in \f. Coverage of the unique set was over 99.0%
complete to at least 26.12\%. Crystal decay was monitored by measuring 200
reflexions per frame.
;

_diffrn_ambient_temperature      180(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  'Stoe IPDS'
_diffrn_measurement_method       \f
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.1
_diffrn_reflns_number            25265
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         26.12
_reflns_number_total             5044
_reflns_number_gt                4487
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'IPDS software, 2.93 (Stoe, 2000)'
_computing_cell_refinement       'IPDS software, 2.93 (Stoe, 2000)'
_computing_data_reduction        'Stoe, Xred-1.07, 1996'
_computing_structure_solution    'SIR-97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0459P)^2^+0.1917P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_number_reflns         5044
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.56850(5) 0.05274(4) 0.885881(19) 0.03154(11) Uani 1 1 d . . .
P2 P 0.60863(4) -0.04138(4) 1.060056(18) 0.02793(11) Uani 1 1 d . . .
O1 O 0.41632(12) -0.00956(10) 0.89881(5) 0.0332(3) Uani 1 1 d . . .
O2 O 0.47888(12) -0.12683(10) 1.04047(5) 0.0293(3) Uani 1 1 d . . .
C1 C 0.40921(18) -0.13152(15) 0.91711(7) 0.0312(4) Uani 1 1 d . . .
H1 H 0.5052 -0.1576 0.9299 0.037 Uiso 1 1 calc R . .
C2 C 0.34486(17) -0.07800(15) 1.02004(7) 0.0298(4) Uani 1 1 d . . .
H2 H 0.3570 0.0075 1.0126 0.036 Uiso 1 1 calc R . .
C3 C 0.30550(18) -0.13966(16) 0.96584(8) 0.0333(4) Uani 1 1 d . . .
H3A H 0.2133 -0.1080 0.9530 0.040 Uiso 1 1 calc R . .
H3B H 0.2909 -0.2235 0.9745 0.040 Uiso 1 1 calc R . .
C4 C 0.3618(2) -0.20618(18) 0.86818(8) 0.0432(5) Uani 1 1 d . . .
H4A H 0.2674 -0.1811 0.8559 0.065 Uiso 1 1 calc R . .
H4B H 0.3581 -0.2883 0.8799 0.065 Uiso 1 1 calc R . .
H4C H 0.4291 -0.1976 0.8370 0.065 Uiso 1 1 calc R . .
C5 C 0.2334(2) -0.09542(18) 1.06500(8) 0.0398(4) Uani 1 1 d . . .
H5A H 0.2211 -0.1793 1.0722 0.060 Uiso 1 1 calc R . .
H5B H 0.1433 -0.0619 1.0523 0.060 Uiso 1 1 calc R . .
H5C H 0.2636 -0.0564 1.0997 0.060 Uiso 1 1 calc R . .
C11 C 0.67810(17) 0.02078(13) 0.94673(7) 0.0286(4) Uani 1 1 d . . .
C12 C 0.79375(17) -0.04118(15) 0.93131(7) 0.0312(4) Uani 1 1 d . . .
C13 C 0.79362(19) -0.07729(15) 0.87152(8) 0.0328(4) Uani 1 1 d . . .
C14 C 0.67512(18) -0.04543(16) 0.84273(7) 0.0331(4) Uani 1 1 d . . .
C21 C 0.63815(17) 0.06109(14) 1.00297(7) 0.0280(3) Uani 1 1 d . . .
C22 C 0.6242(2) 0.17225(14) 1.02227(8) 0.0337(4) Uani 1 1 d . . .
C23 C 0.5694(2) 0.17994(15) 1.08048(8) 0.0348(4) Uani 1 1 d . . .
C24 C 0.53813(19) 0.07517(15) 1.10399(7) 0.0318(4) Uani 1 1 d . . .
C121 C 0.91728(18) -0.06780(16) 0.96880(8) 0.0387(4) Uani 1 1 d . . .
H12A H 0.8940 -0.0458 1.0076 0.058 Uiso 1 1 calc R . .
H12B H 1.0002 -0.0233 0.9562 0.058 Uiso 1 1 calc R . .
H12C H 0.9384 -0.1517 0.9672 0.058 Uiso 1 1 calc R . .
C131 C 0.9223(2) -0.13911(18) 0.84809(9) 0.0457(5) Uani 1 1 d . . .
H13A H 0.9163 -0.1413 0.8070 0.069 Uiso 1 1 calc R . .
H13B H 0.9259 -0.2192 0.8628 0.069 Uiso 1 1 calc R . .
H13C H 1.0083 -0.0969 0.8594 0.069 Uiso 1 1 calc R . .
C141 C 0.64403(19) -0.06752(17) 0.78265(8) 0.0362(4) Uani 1 1 d . . .
C142 C 0.5864(2) 0.02055(19) 0.74881(8) 0.0445(5) Uani 1 1 d . . .
H142 H 0.5691 0.0957 0.7644 0.053 Uiso 1 1 calc R . .
C143 C 0.5540(3) -0.0006(2) 0.69260(10) 0.0575(6) Uani 1 1 d . . .
H143 H 0.5153 0.0600 0.6700 0.069 Uiso 1 1 calc R . .
C144 C 0.5785(3) -0.1106(3) 0.66966(10) 0.0609(6) Uani 1 1 d . . .
H144 H 0.5570 -0.1253 0.6313 0.073 Uiso 1 1 calc R . .
C145 C 0.6337(3) -0.1978(2) 0.70256(10) 0.0561(6) Uani 1 1 d . . .
H145 H 0.6504 -0.2729 0.6868 0.067 Uiso 1 1 calc R . .
C146 C 0.6655(2) -0.17737(19) 0.75874(9) 0.0454(5) Uani 1 1 d . . .
H146 H 0.7023 -0.2391 0.7812 0.054 Uiso 1 1 calc R . .
C221 C 0.6656(3) 0.28029(17) 0.99010(9) 0.0555(6) Uani 1 1 d . . .
H22A H 0.7430 0.3203 1.0098 0.083 Uiso 1 1 calc R . .
H22B H 0.5838 0.3328 0.9872 0.083 Uiso 1 1 calc R . .
H22C H 0.6972 0.2582 0.9523 0.083 Uiso 1 1 calc R . .
C231 C 0.5588(3) 0.29750(17) 1.10933(9) 0.0507(5) Uani 1 1 d . . .
H23A H 0.4758 0.3397 1.0950 0.076 Uiso 1 1 calc R . .
H23B H 0.6447 0.3431 1.1017 0.076 Uiso 1 1 calc R . .
H23C H 0.5489 0.2859 1.1500 0.076 Uiso 1 1 calc R . .
C241 C 0.47502(19) 0.05108(17) 1.15932(7) 0.0347(4) Uani 1 1 d . . .
C242 C 0.3589(2) 0.1149(2) 1.17871(8) 0.0462(5) Uani 1 1 d . . .
H242 H 0.3252 0.1796 1.1574 0.055 Uiso 1 1 calc R . .
C243 C 0.2916(3) 0.0851(2) 1.22895(9) 0.0552(6) Uani 1 1 d . . .
H243 H 0.2127 0.1294 1.2417 0.066 Uiso 1 1 calc R . .
C244 C 0.3392(3) -0.0082(2) 1.25993(9) 0.0594(7) Uani 1 1 d . . .
H244 H 0.2934 -0.0285 1.2941 0.071 Uiso 1 1 calc R . .
C245 C 0.4532(3) -0.0722(2) 1.24145(9) 0.0586(6) Uani 1 1 d . . .
H245 H 0.4854 -0.1371 1.2629 0.070 Uiso 1 1 calc R . .
C246 C 0.5220(2) -0.04309(18) 1.19166(8) 0.0432(4) Uani 1 1 d . . .
H246 H 0.6015 -0.0876 1.1796 0.052 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 0.0335(2) 0.0264(2) 0.0347(2) 0.00428(19) 0.00301(19) 0.00500(19)
P2 0.0276(2) 0.0222(2) 0.0339(2) 0.00322(18) -0.00479(17) 0.00155(18)
O1 0.0284(6) 0.0334(6) 0.0377(7) 0.0050(5) -0.0009(5) 0.0074(5)
O2 0.0274(6) 0.0217(6) 0.0389(7) 0.0048(5) -0.0052(5) 0.0006(5)
C1 0.0265(9) 0.0298(8) 0.0374(9) 0.0022(7) -0.0019(7) 0.0027(7)
C2 0.0245(8) 0.0287(8) 0.0363(9) 0.0039(7) -0.0029(7) 0.0040(6)
C3 0.0257(8) 0.0363(9) 0.0379(10) 0.0025(8) -0.0012(8) -0.0012(7)
C4 0.0410(11) 0.0461(11) 0.0427(11) -0.0072(9) 0.0047(9) -0.0067(9)
C5 0.0319(9) 0.0503(11) 0.0372(10) -0.0006(9) -0.0001(8) -0.0009(8)
C11 0.0280(8) 0.0209(8) 0.0370(9) 0.0026(7) 0.0054(7) -0.0017(6)
C12 0.0274(8) 0.0231(8) 0.0431(10) 0.0045(8) 0.0028(7) -0.0043(7)
C13 0.0289(9) 0.0262(9) 0.0433(10) 0.0042(7) 0.0093(7) 0.0001(7)
C14 0.0353(9) 0.0283(9) 0.0358(9) 0.0054(8) 0.0070(7) -0.0019(8)
C21 0.0245(8) 0.0242(8) 0.0352(9) 0.0023(7) -0.0016(7) 0.0003(7)
C22 0.0412(10) 0.0230(8) 0.0369(10) 0.0025(7) 0.0008(8) -0.0021(7)
C23 0.0432(10) 0.0254(8) 0.0358(9) -0.0021(7) -0.0020(8) 0.0024(8)
C24 0.0331(9) 0.0304(9) 0.0319(9) 0.0016(7) -0.0068(7) 0.0017(7)
C121 0.0267(8) 0.0369(10) 0.0526(11) 0.0033(8) 0.0015(8) 0.0014(7)
C131 0.0375(10) 0.0438(11) 0.0558(13) 0.0015(9) 0.0164(10) 0.0067(9)
C141 0.0333(9) 0.0391(10) 0.0361(9) 0.0035(8) 0.0106(8) -0.0044(8)
C142 0.0460(11) 0.0445(12) 0.0432(11) 0.0066(8) 0.0038(9) -0.0060(9)
C143 0.0628(14) 0.0667(15) 0.0429(12) 0.0141(11) -0.0017(11) -0.0154(12)
C144 0.0599(15) 0.0845(18) 0.0384(11) -0.0055(12) 0.0050(11) -0.0162(13)
C145 0.0580(14) 0.0637(15) 0.0467(13) -0.0143(11) 0.0128(11) -0.0104(12)
C146 0.0450(11) 0.0456(12) 0.0454(12) -0.0030(9) 0.0108(10) -0.0007(9)
C221 0.0932(18) 0.0235(10) 0.0497(13) 0.0014(9) 0.0153(12) -0.0102(10)
C231 0.0818(16) 0.0296(10) 0.0408(11) -0.0060(8) 0.0021(11) -0.0015(10)
C241 0.0396(9) 0.0358(9) 0.0287(8) -0.0022(8) -0.0052(7) -0.0067(8)
C242 0.0477(12) 0.0552(13) 0.0357(11) -0.0034(9) -0.0043(9) 0.0025(10)
C243 0.0482(12) 0.0755(16) 0.0419(12) -0.0152(12) 0.0029(10) -0.0103(11)
C244 0.0735(16) 0.0700(16) 0.0348(12) -0.0041(11) 0.0067(11) -0.0308(13)
C245 0.0903(18) 0.0504(13) 0.0351(11) 0.0083(9) -0.0031(12) -0.0146(13)
C246 0.0570(12) 0.0372(10) 0.0354(9) 0.0037(9) -0.0051(9) -0.0050(10)

_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 O1 1.6311(13) . ?
P1 C11 1.8148(18) . ?
P1 C14 1.8226(19) . ?
P2 O2 1.6332(12) . ?
P2 C21 1.8140(17) . ?
P2 C24 1.8186(18) . ?
O1 C1 1.462(2) . ?
O2 C2 1.4644(19) . ?
C1 C4 1.510(3) . ?
C1 C3 1.519(2) . ?
C2 C5 1.512(3) . ?
C2 C3 1.515(3) . ?
C11 C12 1.351(2) . ?
C11 C21 1.464(2) . ?
C12 C13 1.480(3) . ?
C12 C121 1.498(2) . ?
C13 C14 1.360(3) . ?
C13 C131 1.511(2) . ?
C14 C141 1.480(3) . ?
C21 C22 1.357(2) . ?
C22 C23 1.480(3) . ?
C22 C221 1.504(3) . ?
C23 C24 1.354(2) . ?
C23 C231 1.512(2) . ?
C24 C241 1.470(2) . ?
C141 C146 1.393(3) . ?
C141 C142 1.398(3) . ?
C142 C143 1.392(3) . ?
C143 C144 1.390(4) . ?
C144 C145 1.369(4) . ?
C145 C146 1.388(3) . ?
C241 C242 1.394(3) . ?
C241 C246 1.395(3) . ?
C242 C243 1.394(3) . ?
C243 C244 1.371(4) . ?
C244 C245 1.372(4) . ?
C245 C246 1.390(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
O1 P1 C11 105.24(7) . . ?
O1 P1 C14 108.82(7) . . ?
C11 P1 C14 90.61(8) . . ?
O2 P2 C21 106.72(7) . . ?
O2 P2 C24 109.14(7) . . ?
C21 P2 C24 90.73(8) . . ?
C1 O1 P1 120.84(10) . . ?
C2 O2 P2 120.87(10) . . ?
O1 C1 C4 108.86(14) . . ?
O1 C1 C3 108.36(14) . . ?
C4 C1 C3 111.24(15) . . ?
O2 C2 C5 108.36(14) . . ?
O2 C2 C3 108.44(14) . . ?
C5 C2 C3 111.70(14) . . ?
C2 C3 C1 117.55(14) . . ?
C12 C11 C21 128.37(16) . . ?
C12 C11 P1 110.42(13) . . ?
C21 C11 P1 121.21(12) . . ?
C11 C12 C13 113.96(15) . . ?
C11 C12 C121 124.94(17) . . ?
C13 C12 C121 121.03(15) . . ?
C14 C13 C12 114.16(16) . . ?
C14 C13 C131 126.85(18) . . ?
C12 C13 C131 118.93(17) . . ?
C13 C14 C141 127.07(17) . . ?
C13 C14 P1 109.56(14) . . ?
C141 C14 P1 122.62(13) . . ?
C22 C21 C11 128.94(15) . . ?
C22 C21 P2 109.67(13) . . ?
C11 C21 P2 121.31(12) . . ?
C21 C22 C23 113.93(15) . . ?
C21 C22 C221 124.84(17) . . ?
C23 C22 C221 121.16(16) . . ?
C24 C23 C22 114.18(15) . . ?
C24 C23 C231 125.75(17) . . ?
C22 C23 C231 120.01(16) . . ?
C23 C24 C241 128.56(17) . . ?
C23 C24 P2 109.33(13) . . ?
C241 C24 P2 121.66(13) . . ?
C146 C141 C142 118.06(18) . . ?
C146 C141 C14 121.26(18) . . ?
C142 C141 C14 120.62(17) . . ?
C143 C142 C141 120.8(2) . . ?
C144 C143 C142 119.8(2) . . ?
C145 C144 C143 119.8(2) . . ?
C144 C145 C146 120.6(2) . . ?
C145 C146 C141 120.8(2) . . ?
C242 C241 C246 118.10(18) . . ?
C242 C241 C24 121.06(17) . . ?
C246 C241 C24 120.61(18) . . ?
C243 C242 C241 120.8(2) . . ?
C244 C243 C242 120.1(2) . . ?
C243 C244 C245 119.9(2) . . ?
C244 C245 C246 120.7(2) . . ?
C245 C246 C241 120.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.12
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035