Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2006


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'David Fox'
_publ_contact_author_address     
;
Department of Chemistry
University of Cambridge
University Chemical Laboratory
Lensfield Road
Cambridge
CB2 1EW
UNITED KINGDOM
;

_publ_contact_author_email       DJF34@CAM.AC.UK

_publ_section_title              
;
Asymmetric synthesis of orthogonally protected
trans-cyclopropane ?-amino acids via intramolecular ring closure
;
loop_
_publ_author_name
'David Fox'
'Daniel Sejer Pedersen'
'Stuart Warren'

data_sw0411
_database_code_depnum_ccdc_archive 'CCDC 600428'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H29 O4 P'
_chemical_formula_sum            'C23 H29 O4 P'
_chemical_formula_weight         400.43
_chemical_absolute_configuration 
;
The absolute structure was determined reliably (Flack parameter -0.08(8)).
;

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           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.8939(2)
_cell_length_b                   8.5144(3)
_cell_length_c                   11.3355(4)
_cell_angle_alpha                82.108(2)
_cell_angle_beta                 87.448(2)
_cell_angle_gamma                82.337(2)
_cell_volume                     558.23(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4748
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             214
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
No unusual features.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_reflns_number            5699
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         27.56
_reflns_number_total             3689
_reflns_number_gt                3581
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 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^)+(0.0497P)^2^+0.1145P] 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   -0.08(8)
_refine_ls_number_reflns         3689
_refine_ls_number_parameters     257
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.139
_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 0.27378(6) 0.25996(5) 0.74306(4) 0.02163(13) Uani 1 1 d . . .
O1 O 0.9852(3) 0.6434(3) 0.40524(19) 0.0617(7) Uani 1 1 d . . .
O2 O 0.7425(3) 0.7352(2) 0.25475(15) 0.0353(4) Uani 1 1 d . . .
O3 O 0.4797(2) 0.24963(19) 0.64827(13) 0.0274(3) Uani 1 1 d . . .
O4 O 0.0800(2) 0.38322(17) 0.70718(14) 0.0288(4) Uani 1 1 d . . .
C1 C 0.7985(4) 0.6600(3) 0.3641(2) 0.0374(6) Uani 1 1 d . . .
C2 C 0.5938(4) 0.6015(3) 0.4265(2) 0.0373(6) Uani 1 1 d . . .
H2 H 0.4513 0.6141 0.3795 0.045 Uiso 1 1 calc R . .
C3 C 0.6337(4) 0.4558(3) 0.5190(2) 0.0303(5) Uani 1 1 d . . .
H3 H 0.7977 0.4110 0.5318 0.036 Uiso 1 1 calc R . .
C4 C 0.4690(4) 0.3350(3) 0.52725(19) 0.0315(5) Uani 1 1 d . . .
H4 H 0.3102 0.3888 0.5103 0.038 Uiso 1 1 calc R . .
C5 C 0.5414(6) 0.2098(4) 0.4423(3) 0.0552(8) Uani 1 1 d . . .
H5A H 0.5527 0.2656 0.3601 0.066 Uiso 1 1 calc R . .
H5B H 0.6956 0.1547 0.4638 0.066 Uiso 1 1 calc R . .
C6 C 0.3784(8) 0.0855(5) 0.4446(4) 0.0835(13) Uani 1 1 d . . .
H6A H 0.4273 0.0159 0.3837 0.125 Uiso 1 1 calc R . .
H6B H 0.2232 0.1392 0.4285 0.125 Uiso 1 1 calc R . .
H6C H 0.3797 0.0211 0.5233 0.125 Uiso 1 1 calc R . .
C7 C 0.5636(6) 0.6123(4) 0.5585(3) 0.0556(8) Uani 1 1 d . . .
H7A H 0.6797 0.6611 0.5967 0.067 Uiso 1 1 calc R . .
H7B H 0.4055 0.6340 0.5910 0.067 Uiso 1 1 calc R . .
C8 C 0.9150(5) 0.8061(3) 0.1740(2) 0.0387(6) Uani 1 1 d . . .
C9 C 1.0044(8) 0.9363(4) 0.2288(3) 0.0733(12) Uani 1 1 d . . .
H9A H 1.0933 0.8890 0.2988 0.110 Uiso 1 1 calc R . .
H9B H 0.8756 1.0115 0.2527 0.110 Uiso 1 1 calc R . .
H9C H 1.1027 0.9931 0.1704 0.110 Uiso 1 1 calc R . .
C10 C 0.7788(5) 0.8729(4) 0.0636(3) 0.0525(7) Uani 1 1 d . . .
H10A H 0.6480 0.9484 0.0850 0.079 Uiso 1 1 calc R . .
H10B H 0.7234 0.7852 0.0302 0.079 Uiso 1 1 calc R . .
H10C H 0.8771 0.9282 0.0043 0.079 Uiso 1 1 calc R . .
C11 C 1.1038(5) 0.6771(4) 0.1446(3) 0.0580(8) Uani 1 1 d . . .
H11A H 1.1792 0.6260 0.2180 0.087 Uiso 1 1 calc R . .
H11B H 1.2162 0.7250 0.0895 0.087 Uiso 1 1 calc R . .
H11C H 1.0380 0.5969 0.1073 0.087 Uiso 1 1 calc R . .
C12 C 0.4118(3) 0.2900(3) 0.87553(19) 0.0242(4) Uani 1 1 d . . .
C13 C 0.3055(4) 0.2554(3) 0.9860(2) 0.0320(5) Uani 1 1 d . . .
H13 H 0.1703 0.2050 0.9921 0.038 Uiso 1 1 calc R . .
C14 C 0.3957(5) 0.2938(3) 1.0874(2) 0.0410(6) Uani 1 1 d . . .
H14 H 0.3229 0.2695 1.1630 0.049 Uiso 1 1 calc R . .
C15 C 0.5928(5) 0.3682(3) 1.0785(2) 0.0410(6) Uani 1 1 d . . .
H15 H 0.6537 0.3961 1.1478 0.049 Uiso 1 1 calc R . .
C16 C 0.7000(4) 0.4015(3) 0.9692(2) 0.0360(5) Uani 1 1 d . . .
H16 H 0.8357 0.4513 0.9637 0.043 Uiso 1 1 calc R . .
C17 C 0.6115(3) 0.3629(3) 0.8672(2) 0.0284(5) Uani 1 1 d . . .
H17 H 0.6863 0.3859 0.7921 0.034 Uiso 1 1 calc R . .
C18 C 0.1927(3) 0.0619(3) 0.76627(19) 0.0249(4) Uani 1 1 d . . .
C19 C 0.3389(4) -0.0682(3) 0.8192(2) 0.0324(5) Uani 1 1 d . . .
H19 H 0.4764 -0.0520 0.8538 0.039 Uiso 1 1 calc R . .
C20 C 0.2827(5) -0.2216(3) 0.8211(3) 0.0452(6) Uani 1 1 d . . .
H20 H 0.3828 -0.3106 0.8566 0.054 Uiso 1 1 calc R . .
C21 C 0.0821(5) -0.2460(3) 0.7718(3) 0.0485(7) Uani 1 1 d . . .
H21 H 0.0456 -0.3514 0.7723 0.058 Uiso 1 1 calc R . .
C22 C -0.0641(5) -0.1175(3) 0.7221(3) 0.0469(7) Uani 1 1 d . . .
H22 H -0.2031 -0.1345 0.6894 0.056 Uiso 1 1 calc R . .
C23 C -0.0109(4) 0.0375(3) 0.7191(2) 0.0334(5) Uani 1 1 d . . .
H23 H -0.1135 0.1260 0.6850 0.040 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 0.0203(2) 0.0217(3) 0.0226(3) 0.00031(19) -0.00147(18) -0.00493(17)
O1 0.0453(11) 0.0947(18) 0.0444(12) 0.0261(12) -0.0159(9) -0.0379(12)
O2 0.0368(9) 0.0389(10) 0.0278(9) 0.0095(7) -0.0035(7) -0.0091(7)
O3 0.0245(7) 0.0342(8) 0.0225(8) 0.0022(6) 0.0008(6) -0.0064(6)
O4 0.0257(7) 0.0242(8) 0.0355(9) 0.0006(7) -0.0063(6) -0.0017(6)
C1 0.0408(13) 0.0400(14) 0.0317(13) 0.0062(11) -0.0038(11) -0.0172(11)
C2 0.0352(12) 0.0421(14) 0.0324(13) 0.0088(11) -0.0017(10) -0.0107(10)
C3 0.0318(11) 0.0375(12) 0.0222(11) 0.0035(9) -0.0023(9) -0.0133(9)
C4 0.0344(11) 0.0438(14) 0.0176(10) 0.0044(9) -0.0039(9) -0.0168(10)
C5 0.071(2) 0.071(2) 0.0318(14) -0.0126(14) 0.0081(13) -0.0347(17)
C6 0.120(3) 0.091(3) 0.059(2) -0.039(2) 0.019(2) -0.064(3)
C7 0.079(2) 0.0470(17) 0.0445(17) -0.0084(14) 0.0210(15) -0.0276(16)
C8 0.0476(14) 0.0417(14) 0.0265(12) 0.0048(10) 0.0044(10) -0.0164(11)
C9 0.113(3) 0.063(2) 0.053(2) 0.0036(17) 0.005(2) -0.058(2)
C10 0.0585(17) 0.0578(19) 0.0345(15) 0.0122(13) 0.0022(13) -0.0034(14)
C11 0.0440(15) 0.078(2) 0.0464(17) -0.0017(16) 0.0014(13) 0.0050(15)
C12 0.0252(9) 0.0231(10) 0.0242(10) -0.0020(8) -0.0030(8) -0.0027(8)
C13 0.0335(11) 0.0332(12) 0.0292(12) -0.0018(10) 0.0007(9) -0.0069(9)
C14 0.0471(14) 0.0490(16) 0.0265(12) -0.0045(11) 0.0007(10) -0.0059(12)
C15 0.0482(14) 0.0461(15) 0.0313(13) -0.0117(11) -0.0118(11) -0.0044(11)
C16 0.0329(11) 0.0374(13) 0.0395(14) -0.0056(11) -0.0094(10) -0.0083(10)
C17 0.0250(10) 0.0291(11) 0.0305(12) -0.0018(9) -0.0003(8) -0.0039(8)
C18 0.0270(10) 0.0220(10) 0.0258(11) -0.0033(8) 0.0036(8) -0.0054(8)
C19 0.0367(11) 0.0277(12) 0.0307(12) 0.0001(9) 0.0010(9) -0.0009(9)
C20 0.0638(17) 0.0224(12) 0.0454(15) -0.0008(11) 0.0125(13) 0.0007(11)
C21 0.0651(18) 0.0266(13) 0.0584(18) -0.0172(13) 0.0231(14) -0.0185(12)
C22 0.0412(14) 0.0428(15) 0.0649(19) -0.0252(14) 0.0077(13) -0.0191(12)
C23 0.0269(10) 0.0326(13) 0.0430(14) -0.0092(10) 0.0003(9) -0.0078(9)

_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 O4 1.4750(14) . ?
P1 O3 1.5864(15) . ?
P1 C18 1.796(2) . ?
P1 C12 1.803(2) . ?
O1 C1 1.198(3) . ?
O2 C1 1.348(3) . ?
O2 C8 1.471(3) . ?
O3 C4 1.462(3) . ?
C1 C2 1.481(3) . ?
C2 C3 1.510(3) . ?
C2 C7 1.513(4) . ?
C2 H2 1.0000 . ?
C3 C7 1.465(4) . ?
C3 C4 1.497(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.539(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.518(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.505(4) . ?
C8 C11 1.516(4) . ?
C8 C10 1.519(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.388(3) . ?
C12 C17 1.395(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.387(3) . ?
C18 C19 1.393(3) . ?
C19 C20 1.387(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.371(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(3) . ?
C22 H22 0.9500 . ?
C23 H23 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
O4 P1 O3 114.64(9) . . ?
O4 P1 C18 112.50(9) . . ?
O3 P1 C18 104.21(9) . . ?
O4 P1 C12 114.08(9) . . ?
O3 P1 C12 102.73(9) . . ?
C18 P1 C12 107.72(10) . . ?
C1 O2 C8 120.92(19) . . ?
C4 O3 P1 123.80(14) . . ?
O1 C1 O2 125.4(2) . . ?
O1 C1 C2 124.8(2) . . ?
O2 C1 C2 109.7(2) . . ?
C1 C2 C3 117.1(2) . . ?
C1 C2 C7 117.8(2) . . ?
C3 C2 C7 57.99(17) . . ?
C1 C2 H2 117.0 . . ?
C3 C2 H2 117.0 . . ?
C7 C2 H2 117.0 . . ?
C7 C3 C4 120.4(2) . . ?
C7 C3 C2 61.13(19) . . ?
C4 C3 C2 118.12(19) . . ?
C7 C3 H3 115.4 . . ?
C4 C3 H3 115.4 . . ?
C2 C3 H3 115.4 . . ?
O3 C4 C3 106.96(16) . . ?
O3 C4 C5 106.8(2) . . ?
C3 C4 C5 111.3(2) . . ?
O3 C4 H4 110.6 . . ?
C3 C4 H4 110.6 . . ?
C5 C4 H4 110.6 . . ?
C6 C5 C4 113.9(3) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 C2 60.89(18) . . ?
C3 C7 H7A 117.7 . . ?
C2 C7 H7A 117.7 . . ?
C3 C7 H7B 117.7 . . ?
C2 C7 H7B 117.7 . . ?
H7A C7 H7B 114.8 . . ?
O2 C8 C9 109.8(2) . . ?
O2 C8 C11 110.0(2) . . ?
C9 C8 C11 112.5(3) . . ?
O2 C8 C10 102.6(2) . . ?
C9 C8 C10 111.6(3) . . ?
C11 C8 C10 110.0(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 119.6(2) . . ?
C13 C12 P1 119.41(16) . . ?
C17 C12 P1 120.62(17) . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
C23 C18 C19 119.8(2) . . ?
C23 C18 P1 118.28(17) . . ?
C19 C18 P1 121.57(17) . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 119.6(2) . . ?
C18 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?

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
O4 P1 O3 C4 -9.45(19) . . . . ?
C18 P1 O3 C4 113.95(17) . . . . ?
C12 P1 O3 C4 -133.77(17) . . . . ?
C8 O2 C1 O1 -0.2(4) . . . . ?
C8 O2 C1 C2 179.5(2) . . . . ?
O1 C1 C2 C3 -28.1(4) . . . . ?
O2 C1 C2 C3 152.2(2) . . . . ?
O1 C1 C2 C7 38.1(4) . . . . ?
O2 C1 C2 C7 -141.6(2) . . . . ?
C1 C2 C3 C7 107.3(3) . . . . ?
C1 C2 C3 C4 -141.5(2) . . . . ?
C7 C2 C3 C4 111.1(3) . . . . ?
P1 O3 C4 C3 113.62(18) . . . . ?
P1 O3 C4 C5 -127.14(18) . . . . ?
C7 C3 C4 O3 -84.5(3) . . . . ?
C2 C3 C4 O3 -155.7(2) . . . . ?
C7 C3 C4 C5 159.2(3) . . . . ?
C2 C3 C4 C5 88.0(3) . . . . ?
O3 C4 C5 C6 64.8(3) . . . . ?
C3 C4 C5 C6 -178.8(3) . . . . ?
C4 C3 C7 C2 -107.5(2) . . . . ?
C1 C2 C7 C3 -106.1(2) . . . . ?
C1 O2 C8 C9 -62.2(3) . . . . ?
C1 O2 C8 C11 62.0(3) . . . . ?
C1 O2 C8 C10 179.0(2) . . . . ?
O4 P1 C12 C13 75.5(2) . . . . ?
O3 P1 C12 C13 -159.84(18) . . . . ?
C18 P1 C12 C13 -50.2(2) . . . . ?
O4 P1 C12 C17 -97.87(18) . . . . ?
O3 P1 C12 C17 26.82(19) . . . . ?
C18 P1 C12 C17 136.47(17) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?
P1 C12 C13 C14 -172.90(19) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C12 0.2(4) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
P1 C12 C17 C16 172.59(18) . . . . ?
O4 P1 C18 C23 17.4(2) . . . . ?
O3 P1 C18 C23 -107.41(18) . . . . ?
C12 P1 C18 C23 143.96(18) . . . . ?
O4 P1 C18 C19 -169.16(17) . . . . ?
O3 P1 C18 C19 66.1(2) . . . . ?
C12 P1 C18 C19 -42.6(2) . . . . ?
C23 C18 C19 C20 1.9(4) . . . . ?
P1 C18 C19 C20 -171.5(2) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C20 C21 C22 C23 1.0(4) . . . . ?
C19 C18 C23 C22 -1.8(4) . . . . ?
P1 C18 C23 C22 171.7(2) . . . . ?
C21 C22 C23 C18 0.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.068