 
data_02src207
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C23 H23 O3 P' 
_chemical_formula_weight          378.38 
 
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    P212121
 
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                    5.788(5) 
_cell_length_b                    17.499(5) 
_cell_length_c                    19.463(5) 
_cell_angle_alpha                 90.000(5) 
_cell_angle_beta                  90.000(5) 
_cell_angle_gamma                 90.000(5) 
_cell_volume                      1971.3(19) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     5841	 
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.15 
_exptl_crystal_size_mid           0.04 
_exptl_crystal_size_min           0.03 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.275 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              800 
_exptl_absorpt_coefficient_mu     0.160 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9765 
_exptl_absorpt_correction_T_max   0.9952 
_exptl_absorpt_process_details    'Sortav (Blessing, 1997)'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       120(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD'
_diffrn_measurement_method        'Φ & ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10345 
_diffrn_reflns_av_R_equivalents   0.0956 
_diffrn_reflns_av_sigmaI/netI     0.1135 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        -19 
_diffrn_reflns_limit_k_max        20 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        23 
_diffrn_reflns_theta_min          3.13 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              3383 
_reflns_number_gt                 2169 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_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)+(0.0307P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0034(9) 
_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    0.66(17) 
_refine_ls_number_reflns          3383 
_refine_ls_number_parameters      246 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1106 
_refine_ls_R_factor_gt            0.0552 
_refine_ls_wR_factor_ref          0.1102 
_refine_ls_wR_factor_gt           0.0939 
_refine_ls_goodness_of_fit_ref    0.981 
_refine_ls_restrained_S_all       0.981 
_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 0.9902(2) 0.11836(6) 0.21625(5) 0.0347(3) Uani 1 1 d . . . 
O1 O 1.2440(4) 0.11104(16) 0.20773(13) 0.0391(7) Uani 1 1 d . . . 
O2 O 0.5024(6) -0.03389(15) 0.09192(14) 0.0497(8) Uani 1 1 d . . . 
O3 O 0.7370(6) -0.13387(17) 0.10814(17) 0.0577(9) Uani 1 1 d . . . 
C1 C 0.8976(7) 0.2168(2) 0.2158(2) 0.0346(10) Uani 1 1 d . . . 
C2 C 0.6833(8) 0.2403(2) 0.2406(2) 0.0430(12) Uani 1 1 d . . . 
H2 H 0.5751 0.2035 0.2564 0.052 Uiso 1 1 calc R . . 
C3 C 0.6279(8) 0.3172(2) 0.2421(2) 0.0443(12) Uani 1 1 d . . . 
H3 H 0.4821 0.3330 0.2595 0.053 Uiso 1 1 calc R . . 
C4 C 0.7824(7) 0.3709(2) 0.2187(2) 0.0437(11) Uani 1 1 d . . . 
H4 H 0.7441 0.4237 0.2207 0.052 Uiso 1 1 calc R . . 
C5 C 0.9934(9) 0.3484(2) 0.1922(2) 0.0447(11) Uani 1 1 d . . . 
H5 H 1.0987 0.3853 0.1748 0.054 Uiso 1 1 calc R . . 
C6 C 1.0499(7) 0.2710(2) 0.1913(2) 0.0416(11) Uani 1 1 d . . . 
H6 H 1.1953 0.2553 0.1735 0.050 Uiso 1 1 calc R . . 
C7 C 0.8936(7) 0.0793(2) 0.2975(2) 0.0348(10) Uani 1 1 d . . . 
C8 C 1.0583(7) 0.0783(2) 0.3501(2) 0.0381(11) Uani 1 1 d . . . 
H8 H 1.2087 0.0980 0.3419 0.046 Uiso 1 1 calc R . . 
C9 C 1.0034(8) 0.0486(2) 0.41434(19) 0.0379(10) Uani 1 1 d . . . 
H9 H 1.1150 0.0489 0.4501 0.045 Uiso 1 1 calc R . . 
C10 C 0.7873(8) 0.0188(2) 0.4259(2) 0.0384(11) Uani 1 1 d . . . 
H10 H 0.7497 -0.0019 0.4696 0.046 Uiso 1 1 calc R . . 
C11 C 0.6234(8) 0.0189(2) 0.3736(2) 0.0388(11) Uani 1 1 d . . . 
H11 H 0.4748 -0.0024 0.3816 0.047 Uiso 1 1 calc R . . 
C12 C 0.6754(7) 0.0497(2) 0.3098(2) 0.0360(10) Uani 1 1 d . . . 
H12 H 0.5616 0.0505 0.2746 0.043 Uiso 1 1 calc R . . 
C13 C 0.8206(7) 0.0706(2) 0.1506(2) 0.0352(11) Uani 1 1 d . . . 
H13 H 0.6538 0.0801 0.1609 0.042 Uiso 1 1 calc R . . 
C14 C 0.8719(7) 0.1046(2) 0.0802(2) 0.0340(10) Uani 1 1 d . . . 
C15 C 0.7096(8) 0.1499(2) 0.0480(2) 0.0356(10) Uani 1 1 d . . . 
H15 H 0.5673 0.1605 0.0704 0.043 Uiso 1 1 calc R . . 
C16 C 0.7517(7) 0.1801(2) -0.0166(2) 0.0371(10) Uani 1 1 d . . . 
H16 H 0.6375 0.2105 -0.0385 0.045 Uiso 1 1 calc R . . 
C17 C 0.9584(8) 0.1662(2) -0.0490(2) 0.0362(11) Uani 1 1 d . . . 
H17 H 0.9871 0.1869 -0.0933 0.043 Uiso 1 1 calc R . . 
C18 C 1.1245(7) 0.1220(2) -0.0169(2) 0.0385(10) Uani 1 1 d . . . 
H18 H 1.2680 0.1127 -0.0390 0.046 Uiso 1 1 calc R . . 
C19 C 1.0815(7) 0.0912(2) 0.0480(2) 0.0364(11) Uani 1 1 d . . . 
H19 H 1.1959 0.0610 0.0701 0.044 Uiso 1 1 calc R . . 
C20 C 0.8608(8) -0.0166(2) 0.1527(2) 0.0419(11) Uani 1 1 d . . . 
H20A H 1.0140 -0.0283 0.1327 0.050 Uiso 1 1 calc R . . 
H20B H 0.8612 -0.0340 0.2011 0.050 Uiso 1 1 calc R . . 
C21 C 0.6773(9) -0.0592(3) 0.1136(2) 0.0416(11) Uani 1 1 d . . . 
C22 C 0.5660(11) -0.1819(3) 0.0744(3) 0.074(2) Uani 1 1 d . . . 
H22A H 0.5557 -0.1689 0.0250 0.089 Uiso 1 1 calc R . . 
H22B H 0.4121 -0.1744 0.0955 0.089 Uiso 1 1 calc R . . 
C23 C 0.6421(13) -0.2623(3) 0.0830(3) 0.089(2) Uani 1 1 d . . . 
H23A H 0.7957 -0.2688 0.0627 0.134 Uiso 1 1 calc R . . 
H23B H 0.5322 -0.2965 0.0601 0.134 Uiso 1 1 calc R . . 
H23C H 0.6485 -0.2748 0.1321 0.134 Uiso 1 1 calc R . . 
 
 
_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 1.484(3) . ? 
P1 C1 1.805(4) . ? 
P1 C7 1.811(4) . ? 
P1 C13 1.815(4) . ? 
O2 C21 1.183(5) . ? 
O3 C21 1.356(5) . ? 
O3 C22 1.456(6) . ? 
C1 C6 1.379(5) . ? 
C1 C2 1.393(6) . ? 
C2 C3 1.383(6) . ? 
C3 C4 1.376(6) . ? 
C4 C5 1.383(6) . ? 
C5 C6 1.394(6) . ? 
C7 C12 1.386(6) . ? 
C7 C8 1.399(5) . ? 
C8 C9 1.391(5) . ? 
C9 C10 1.374(6) . ? 
C10 C11 1.391(6) . ? 
C11 C12 1.387(5) . ? 
C13 C14 1.523(5) . ? 
C13 C20 1.544(6) . ? 
C14 C15 1.379(6) . ? 
C14 C19 1.385(6) . ? 
C15 C16 1.386(6) . ? 
C16 C17 1.374(6) . ? 
C17 C18 1.383(6) . ? 
C18 C19 1.396(6) . ? 
C20 C21 1.504(6) . ? 
C22 C23 1.484(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 
O1 P1 C1 112.06(17) . . ? 
O1 P1 C7 111.75(17) . . ? 
C1 P1 C7 105.87(18) . . ? 
O1 P1 C13 114.64(18) . . ? 
C1 P1 C13 105.97(19) . . ? 
C7 P1 C13 105.92(19) . . ? 
C21 O3 C22 114.8(4) . . ? 
C6 C1 C2 119.1(4) . . ? 
C6 C1 P1 117.9(3) . . ? 
C2 C1 P1 123.0(3) . . ? 
C3 C2 C1 120.0(4) . . ? 
C4 C3 C2 120.5(4) . . ? 
C3 C4 C5 120.2(4) . . ? 
C4 C5 C6 119.3(4) . . ? 
C1 C6 C5 120.9(4) . . ? 
C12 C7 C8 119.3(4) . . ? 
C12 C7 P1 125.0(3) . . ? 
C8 C7 P1 115.7(3) . . ? 
C9 C8 C7 120.5(4) . . ? 
C10 C9 C8 119.8(4) . . ? 
C9 C10 C11 120.1(4) . . ? 
C12 C11 C10 120.5(4) . . ? 
C7 C12 C11 119.9(4) . . ? 
C14 C13 C20 112.4(3) . . ? 
C14 C13 P1 110.4(3) . . ? 
C20 C13 P1 110.8(3) . . ? 
C15 C14 C19 119.3(4) . . ? 
C15 C14 C13 120.0(4) . . ? 
C19 C14 C13 120.7(4) . . ? 
C14 C15 C16 120.7(4) . . ? 
C17 C16 C15 120.1(4) . . ? 
C16 C17 C18 119.8(4) . . ? 
C17 C18 C19 120.0(4) . . ? 
C14 C19 C18 120.0(4) . . ? 
C21 C20 C13 111.7(4) . . ? 
O2 C21 O3 123.4(4) . . ? 
O2 C21 C20 126.8(4) . . ? 
O3 C21 C20 109.7(4) . . ? 
O3 C22 C23 107.1(5) . . ? 
 
_diffrn_measured_fraction_theta_max    0.986 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.986 
_refine_diff_density_max    0.159 
_refine_diff_density_min   -0.225 
_refine_diff_density_rms    0.047 
