data_04src0162
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C32 H21 O3 P'
_chemical_formula_sum
 'C32 H21 O3 P'
_chemical_formula_weight          484.46
 
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)
_symmetry_space_group_name_hall   'P 2ac 2ab'
 
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                    8.48080(10)
_cell_length_b                    11.6611(2)
_cell_length_c                    23.5264(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2326.65(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     20874
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.38
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1008
_exptl_absorpt_coefficient_mu     0.153
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9442
_exptl_absorpt_correction_T_max   0.9701
_exptl_absorpt_process_details    'SORTAV (R.H.Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             20592
_diffrn_reflns_av_R_equivalents   0.0682
_diffrn_reflns_av_sigmaI/netI     0.0504
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -30
_diffrn_reflns_limit_l_max        30
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          27.47
_reflns_number_total              5183
_reflns_number_gt                 4483
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Watkin, Pearce 1995)'
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0449P)²+0.4595P] where P=(Fo²+2Fc²)/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      SHELXL
_refine_ls_extinction_coef        0.0117(14)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.12(8)
_refine_ls_number_reflns          5183
_refine_ls_number_parameters      326
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0502
_refine_ls_R_factor_gt            0.0384
_refine_ls_wR_factor_ref          0.0910
_refine_ls_wR_factor_gt           0.0849
_refine_ls_goodness_of_fit_ref    1.016
_refine_ls_restrained_S_all       1.016
_refine_ls_shift/su_max           0.005
_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
C1 C 0.1362(2) 0.88087(16) 0.91877(7) 0.0218(4) Uani 1 1 d . . .
C2 C 0.0672(2) 0.79206(17) 0.94900(8) 0.0272(4) Uani 1 1 d . . .
H2 H 0.0845 0.7149 0.9377 0.033 Uiso 1 1 calc R . .
C3 C -0.0271(2) 0.81571(18) 0.99568(8) 0.0285(4) Uani 1 1 d . . .
H3 H -0.0727 0.7548 1.0168 0.034 Uiso 1 1 calc R . .
C4 C -0.0543(3) 0.92761(18) 1.01130(8) 0.0313(5) Uani 1 1 d . . .
H4 H -0.1201 0.9444 1.0429 0.038 Uiso 1 1 calc R . .
C5 C 0.0148(2) 1.01554(18) 0.98064(8) 0.0292(5) Uani 1 1 d . . .
H5 H -0.0049 1.0925 0.9919 0.035 Uiso 1 1 calc R . .
C6 C 0.1122(2) 0.99582(16) 0.93388(7) 0.0224(4) Uani 1 1 d . . .
C7 C 0.1860(2) 1.09412(16) 0.90390(8) 0.0221(4) Uani 1 1 d . . .
C8 C 0.2470(2) 1.18568(16) 0.93515(8) 0.0280(4) Uani 1 1 d . . .
H8 H 0.2459 1.1823 0.9755 0.034 Uiso 1 1 calc R . .
C9 C 0.3090(2) 1.28131(17) 0.90840(9) 0.0307(4) Uani 1 1 d . . .
H9 H 0.3493 1.3429 0.9305 0.037 Uiso 1 1 calc R . .
C10 C 0.3126(2) 1.28751(17) 0.84975(9) 0.0296(4) Uani 1 1 d . . .
H10 H 0.3550 1.3531 0.8313 0.036 Uiso 1 1 calc R . .
C11 C 0.2536(2) 1.19709(16) 0.81819(8) 0.0256(4) Uani 1 1 d . . .
H11 H 0.2557 1.2010 0.7779 0.031 Uiso 1 1 calc R . .
C12 C 0.1916(2) 1.10089(16) 0.84453(7) 0.0220(4) Uani 1 1 d . . .
H12 H 0.1526 1.0392 0.8222 0.026 Uiso 1 1 calc R . .
C13 C 0.3645(2) 0.83229(16) 0.75416(8) 0.0228(4) Uani 1 1 d . . .
C14 C 0.4227(2) 0.94448(16) 0.75138(9) 0.0280(4) Uani 1 1 d . . .
H14 H 0.4838 0.9749 0.7817 0.034 Uiso 1 1 calc R . .
C15 C 0.3906(2) 1.00957(17) 0.70457(9) 0.0313(5) Uani 1 1 d . . .
H15 H 0.4332 1.0847 0.7017 0.038 Uiso 1 1 calc R . .
C16 C 0.2944(2) 0.96633(15) 0.66020(8) 0.0263(4) Uani 1 1 d . . .
C17 C 0.2535(3) 1.03564(17) 0.61285(9) 0.0347(5) Uani 1 1 d . . .
H17 H 0.2967 1.1105 0.6096 0.042 Uiso 1 1 calc R . .
C18 C 0.1534(3) 0.99641(19) 0.57206(9) 0.0368(5) Uani 1 1 d . . .
H18 H 0.1281 1.0435 0.5404 0.044 Uiso 1 1 calc R . .
C19 C 0.0878(2) 0.88663(18) 0.57680(8) 0.0307(5) Uani 1 1 d . . .
H19 H 0.0157 0.8605 0.5487 0.037 Uiso 1 1 calc R . .
C20 C 0.1262(2) 0.81615(16) 0.62147(8) 0.0242(4) Uani 1 1 d . . .
H20 H 0.0806 0.7419 0.6238 0.029 Uiso 1 1 calc R . .
C21 C 0.2331(2) 0.85293(15) 0.66413(7) 0.0216(4) Uani 1 1 d . . .
C22 C 0.2745(2) 0.78268(15) 0.71211(7) 0.0195(4) Uani 1 1 d . . .
C23 C 0.2191(2) 0.66238(14) 0.71880(7) 0.0189(4) Uani 1 1 d . . .
C24 C 0.2485(2) 0.57494(15) 0.67739(7) 0.0193(4) Uani 1 1 d . . .
C25 C 0.3459(2) 0.59316(16) 0.62908(8) 0.0229(4) Uani 1 1 d . . .
H25 H 0.3888 0.6671 0.6222 0.028 Uiso 1 1 calc R . .
C26 C 0.3786(2) 0.50519(17) 0.59234(8) 0.0279(4) Uani 1 1 d . . .
H26 H 0.4449 0.5186 0.5605 0.034 Uiso 1 1 calc R . .
C27 C 0.3151(2) 0.39511(17) 0.60129(8) 0.0291(5) Uani 1 1 d . . .
H27 H 0.3375 0.3351 0.5752 0.035 Uiso 1 1 calc R . .
C28 C 0.2220(2) 0.37440(15) 0.64710(8) 0.0265(4) Uani 1 1 d . . .
H28 H 0.1787 0.3001 0.6525 0.032 Uiso 1 1 calc R . .
C29 C 0.1887(2) 0.46182(15) 0.68679(8) 0.0212(4) Uani 1 1 d . . .
C30 C 0.1018(2) 0.43836(16) 0.73699(8) 0.0243(4) Uani 1 1 d . . .
H30 H 0.0568 0.3645 0.7424 0.029 Uiso 1 1 calc R . .
C31 C 0.0820(2) 0.52066(16) 0.77763(8) 0.0229(4) Uani 1 1 d . . .
H31 H 0.0282 0.5034 0.8120 0.027 Uiso 1 1 calc R . .
C32 C 0.1421(2) 0.63074(15) 0.76805(7) 0.0201(4) Uani 1 1 d . . .
O1 O 0.23190(16) 0.86084(11) 0.87178(5) 0.0269(3) Uani 1 1 d . . .
O2 O 0.40682(14) 0.76790(11) 0.80207(5) 0.0255(3) Uani 1 1 d . . .
O3 O 0.12287(14) 0.71280(11) 0.81107(5) 0.0224(3) Uani 1 1 d . . .
P1 P 0.28078(6) 0.73297(4) 0.85041(2) 0.02495(13) Uani 1 1 d . . .
 
 
_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 1.386(3) . ?
C1 O1 1.391(2) . ?
C1 C6 1.402(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.395(3) . ?
C6 C7 1.484(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.400(2) . ?
C8 C9 1.384(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.385(3) . ?
C13 C22 1.377(2) . ?
C13 O2 1.401(2) . ?
C13 C14 1.400(3) . ?
C14 C15 1.365(3) . ?
C15 C16 1.418(3) . ?
C16 C17 1.419(3) . ?
C16 C21 1.424(2) . ?
C17 C18 1.360(3) . ?
C18 C19 1.400(3) . ?
C19 C20 1.373(3) . ?
C20 C21 1.419(3) . ?
C21 C22 1.438(2) . ?
C22 C23 1.488(2) . ?
C23 C32 1.380(3) . ?
C23 C24 1.432(2) . ?
C24 C25 1.421(3) . ?
C24 C29 1.431(2) . ?
C25 C26 1.370(3) . ?
C26 C27 1.408(3) . ?
C27 C28 1.358(3) . ?
C28 C29 1.411(3) . ?
C29 C30 1.419(3) . ?
C30 C31 1.365(3) . ?
C31 C32 1.399(3) . ?
C32 O3 1.402(2) . ?
O1 P1 1.6272(13) . ?
O2 P1 1.6130(14) . ?
O3 P1 1.6447(13) . ?
 
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 O1 121.91(16) . . ?
C2 C1 C6 121.56(17) . . ?
O1 C1 C6 116.53(16) . . ?
C1 C2 C3 120.09(18) . . ?
C4 C3 C2 119.83(18) . . ?
C3 C4 C5 119.52(19) . . ?
C4 C5 C6 122.66(19) . . ?
C5 C6 C1 116.32(17) . . ?
C5 C6 C7 119.82(17) . . ?
C1 C6 C7 123.84(16) . . ?
C8 C7 C12 118.04(17) . . ?
C8 C7 C6 119.78(16) . . ?
C12 C7 C6 122.13(16) . . ?
C9 C8 C7 121.17(17) . . ?
C10 C9 C8 120.28(18) . . ?
C9 C10 C11 119.22(19) . . ?
C12 C11 C10 120.97(18) . . ?
C11 C12 C7 120.31(17) . . ?
C22 C13 O2 119.65(16) . . ?
C22 C13 C14 123.69(18) . . ?
O2 C13 C14 116.62(17) . . ?
C15 C14 C13 119.14(19) . . ?
C14 C15 C16 120.74(18) . . ?
C15 C16 C17 121.06(18) . . ?
C15 C16 C21 119.51(18) . . ?
C17 C16 C21 119.39(18) . . ?
C18 C17 C16 120.97(19) . . ?
C17 C18 C19 120.0(2) . . ?
C20 C19 C18 120.9(2) . . ?
C19 C20 C21 120.79(18) . . ?
C20 C21 C16 117.90(17) . . ?
C20 C21 C22 122.62(16) . . ?
C16 C21 C22 119.39(16) . . ?
C13 C22 C21 117.38(16) . . ?
C13 C22 C23 119.69(16) . . ?
C21 C22 C23 122.88(15) . . ?
C32 C23 C24 117.59(15) . . ?
C32 C23 C22 119.36(15) . . ?
C24 C23 C22 122.97(15) . . ?
C25 C24 C29 117.89(16) . . ?
C25 C24 C23 122.61(16) . . ?
C29 C24 C23 119.31(16) . . ?
C26 C25 C24 120.70(18) . . ?
C25 C26 C27 120.73(18) . . ?
C28 C27 C26 120.22(17) . . ?
C27 C28 C29 120.89(18) . . ?
C28 C29 C30 121.05(16) . . ?
C28 C29 C24 119.51(17) . . ?
C30 C29 C24 119.39(16) . . ?
C31 C30 C29 120.74(17) . . ?
C30 C31 C32 119.19(17) . . ?
C23 C32 O3 118.59(15) . . ?
C23 C32 C31 123.55(16) . . ?
O3 C32 C31 117.87(16) . . ?
C1 O1 P1 123.23(12) . . ?
C13 O2 P1 122.20(11) . . ?
C32 O3 P1 114.13(11) . . ?
O2 P1 O1 98.94(7) . . ?
O2 P1 O3 100.31(7) . . ?
O1 P1 O3 95.60(7) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.47
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.340
_refine_diff_density_min   -0.225
_refine_diff_density_rms    0.048
