# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 207/501 data_n151 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H21 F2 O3 P' _chemical_formula_weight 366.33 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' 'F' 'F' 0.0171 0.0103 '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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.96(2) _cell_length_b 30.20(6) _cell_length_c 15.10(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3631(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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_type Philips PW1100 _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 5 h _diffrn_standards_decay_% 0.92 _diffrn_reflns_number 2240 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1584 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 21.00 _reflns_number_total 2240 _reflns_number_gt 1398 _reflns_threshold_expression >2sigma(I) _computing_data_collection Philips control program _computing_cell_refinement Philips _computing_data_reduction Philips _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXtl _computing_publication_material Shelxtl _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^)+(0.1007P)^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 mixed _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 -1.4(4) _refine_ls_number_reflns 2244 _refine_ls_number_parameters 267 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.1266 _refine_ls_R_factor_gt 0.0806 _refine_ls_wR_factor_ref 0.2161 _refine_ls_wR_factor_gt 0.1887 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.491 _refine_ls_shift/su_mean 0.096 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 -0.0682(5) 0.29492(10) -0.2740(2) 0.0361(9) Uani 1 1 d D . . O1 O -0.1727(11) 0.3308(3) -0.3102(5) 0.044(2) Uani 1 1 d D . . O2 O 0.1083(10) 0.2037(3) -0.2004(6) 0.054(3) Uani 1 1 d D . . O3 O -0.3071(12) 0.1875(3) -0.2925(5) 0.056(3) Uani 1 1 d D . . F1 F -0.1889(11) 0.3431(2) -0.1261(5) 0.061(2) Uani 1 1 d D . . F2 F 0.0110(12) 0.3181(2) -0.4571(5) 0.071(3) Uani 1 1 d D . . C2A C 0.2775(16) 0.1967(5) -0.2191(11) 0.081(5) Uiso 1 1 d D . . H2A1 H 0.2993 0.1654 -0.2217 0.122 Uiso 1 1 calc R . . H2A2 H 0.3450 0.2098 -0.1734 0.122 Uiso 1 1 calc R . . H2A3 H 0.3048 0.2100 -0.2751 0.122 Uiso 1 1 calc R . . C3A C -0.3332(19) 0.1465(4) -0.3326(9) 0.065(4) Uiso 1 1 d D . . H3A1 H -0.2452 0.1409 -0.3746 0.097 Uiso 1 1 calc R . . H3A2 H -0.4396 0.1466 -0.3626 0.097 Uiso 1 1 calc R . . H3A3 H -0.3330 0.1237 -0.2883 0.097 Uiso 1 1 calc R . . C1 C -0.0115(15) 0.2563(3) -0.3608(6) 0.033(3) Uiso 1 1 d D . . C2 C 0.0186(18) 0.2733(4) -0.4467(8) 0.049(4) Uiso 1 1 d D . . C3 C 0.0648(18) 0.2487(4) -0.5182(8) 0.053(4) Uiso 1 1 d D . . H3 H 0.0841 0.2623 -0.5725 0.063 Uiso 1 1 calc R . . C4 C 0.0825(19) 0.2046(5) -0.5095(10) 0.069(5) Uiso 1 1 d D . . H4 H 0.1118 0.1872 -0.5579 0.082 Uiso 1 1 calc R . . C5 C 0.0555(18) 0.1852(4) -0.4255(8) 0.060(4) Uiso 1 1 d D . . H5 H 0.0655 0.1547 -0.4187 0.072 Uiso 1 1 calc R . . C6 C 0.0139(16) 0.2115(4) -0.3524(7) 0.044(3) Uiso 1 1 d D . . C7 C -0.0036(13) 0.1859(4) -0.2646(7) 0.041(3) Uiso 1 1 d D . . H7 H 0.0256 0.1548 -0.2750 0.050 Uiso 1 1 calc R . . C8 C -0.1796(13) 0.1881(4) -0.2261(7) 0.038(3) Uiso 1 1 d D . . H8 H -0.1942 0.1609 -0.1918 0.046 Uiso 1 1 calc R . . C9 C -0.2154(17) 0.2250(4) -0.1644(8) 0.046(4) Uiso 1 1 d D . . C10 C -0.2945(17) 0.2139(4) -0.0843(8) 0.053(4) Uiso 1 1 d D . . H10 H -0.3134 0.1841 -0.0718 0.064 Uiso 1 1 calc R . . C11 C -0.346(2) 0.2451(4) -0.0231(9) 0.067(5) Uiso 1 1 d D . . H11 H -0.4014 0.2366 0.0283 0.080 Uiso 1 1 calc R . . C12 C -0.3132(17) 0.2884(4) -0.0395(9) 0.055(4) Uiso 1 1 d D . . H12 H -0.3503 0.3103 -0.0008 0.066 Uiso 1 1 calc R . . C13 C -0.2222(16) 0.2995(4) -0.1160(8) 0.042(3) Uiso 1 1 d D . . C14 C -0.1748(15) 0.2684(3) -0.1811(7) 0.035(3) Uiso 1 1 d D . . C15 C 0.1302(15) 0.3118(4) -0.2247(9) 0.048(4) Uiso 1 1 d D . . H15A H 0.1066 0.3328 -0.1778 0.058 Uiso 1 1 calc R . . H15B H 0.1815 0.2860 -0.1976 0.058 Uiso 1 1 calc R . . C16 C 0.257(2) 0.3325(5) -0.2870(11) 0.081(5) Uiso 1 1 d . . . H16A H 0.2136 0.3606 -0.3079 0.098 Uiso 1 1 calc R . . H16B H 0.2715 0.3133 -0.3380 0.098 Uiso 1 1 calc R . . C17 C 0.423(2) 0.3397(5) -0.2432(11) 0.096(6) Uiso 1 1 d . . . H17A H 0.4085 0.3574 -0.1910 0.144 Uiso 1 1 calc R . . H17B H 0.4974 0.3547 -0.2835 0.144 Uiso 1 1 calc R . . H17C H 0.4711 0.3116 -0.2272 0.144 Uiso 1 1 calc R . . P1' P -0.0233(5) 0.04971(11) -0.1469(2) 0.0468(11) Uani 1 1 d D . . O1' O -0.1564(12) 0.0737(3) -0.1950(6) 0.069(3) Uani 1 1 d D . . O2' O -0.2314(12) -0.0420(3) -0.1651(6) 0.063(3) Uani 1 1 d D . . O3' O 0.1528(13) -0.0543(3) -0.0485(6) 0.066(3) Uani 1 1 d D . . F1' F 0.1232(15) 0.0659(3) -0.3145(6) 0.106(4) Uani 1 1 d D . . F2' F -0.1080(12) 0.1030(3) 0.0067(5) 0.082(3) Uani 1 1 d D . . C3A' C 0.239(2) -0.0899(4) -0.0139(10) 0.076(5) Uiso 1 1 d D . . H3A4 H 0.2984 -0.1048 -0.0605 0.115 Uiso 1 1 calc R . . H3A5 H 0.1613 -0.1100 0.0132 0.115 Uiso 1 1 calc R . . H3A6 H 0.3179 -0.0796 0.0297 0.115 Uiso 1 1 calc R . . C2A' C -0.4032(17) -0.0391(6) -0.1481(13) 0.117(7) Uiso 1 1 d D . . H2A4 H -0.4419 -0.0666 -0.1233 0.176 Uiso 1 1 calc R . . H2A5 H -0.4621 -0.0334 -0.2024 0.176 Uiso 1 1 calc R . . H2A6 H -0.4239 -0.0155 -0.1070 0.176 Uiso 1 1 calc R . . C1' C -0.1004(16) 0.0292(4) -0.0411(6) 0.045(4) Uiso 1 1 d D . . C2' C -0.1364(19) 0.0597(4) 0.0262(9) 0.060(4) Uiso 1 1 d D . . C3' C -0.200(2) 0.0492(5) 0.1079(10) 0.072(5) Uiso 1 1 d D . . H3' H -0.2183 0.0713 0.1498 0.086 Uiso 1 1 calc R . . C4' C -0.236(2) 0.0072(5) 0.1271(12) 0.093(6) Uiso 1 1 d D . . H4' H -0.2762 -0.0004 0.1829 0.111 Uiso 1 1 calc R . . C5' C -0.213(2) -0.0255(6) 0.0619(10) 0.086(6) Uiso 1 1 d D . . H5' H -0.2410 -0.0548 0.0739 0.104 Uiso 1 1 calc R . . C6' C -0.1483(18) -0.0139(4) -0.0213(8) 0.051(4) Uiso 1 1 d D . . C7' C -0.1367(15) -0.0525(4) -0.0883(8) 0.054(4) Uiso 1 1 d D . . H7' H -0.1848 -0.0791 -0.0610 0.065 Uiso 1 1 calc R . . C8' C 0.0401(13) -0.0630(4) -0.1190(7) 0.041(3) Uiso 1 1 d D . . H8' H 0.0456 -0.0948 -0.1324 0.049 Uiso 1 1 calc R . . C9' C 0.0967(17) -0.0383(4) -0.1990(8) 0.048(4) Uiso 1 1 d D . . C10' C 0.1798(19) -0.0652(5) -0.2607(9) 0.063(4) Uiso 1 1 d D . . H10' H 0.1911 -0.0954 -0.2502 0.076 Uiso 1 1 calc R . . C11' C 0.245(2) -0.0467(5) -0.3376(11) 0.079(5) Uiso 1 1 d D . . H11' H 0.3013 -0.0648 -0.3777 0.095 Uiso 1 1 calc R . . C12' C 0.229(2) -0.0025(5) -0.3558(11) 0.079(5) Uiso 1 1 d D . . H12' H 0.2767 0.0102 -0.4060 0.095 Uiso 1 1 calc R . . C13' C 0.1376(19) 0.0221(4) -0.2950(10) 0.065(4) Uiso 1 1 d D . . C14' C 0.0733(15) 0.0069(3) -0.2151(7) 0.040(3) Uiso 1 1 d D . . C15' C 0.1558(18) 0.0835(5) -0.1195(10) 0.074(5) Uiso 1 1 d D . . H15C H 0.1871 0.0999 -0.1722 0.089 Uiso 1 1 calc R . . H15D H 0.1198 0.1051 -0.0757 0.089 Uiso 1 1 calc R . . C16' C 0.306(2) 0.0622(5) -0.0858(12) 0.086(6) Uiso 1 1 d . . . H16C H 0.3419 0.0405 -0.1292 0.103 Uiso 1 1 calc R . . H16D H 0.2754 0.0461 -0.0325 0.103 Uiso 1 1 calc R . . C17' C 0.454(2) 0.0916(5) -0.0643(11) 0.099(6) Uiso 1 1 d . . . H17D H 0.5153 0.0977 -0.1176 0.148 Uiso 1 1 calc R . . H17E H 0.5255 0.0768 -0.0227 0.148 Uiso 1 1 calc R . . H17F H 0.4142 0.1188 -0.0391 0.148 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 0.049(2) 0.0323(18) 0.0275(17) 0.0021(17) 0.0009(19) 0.0029(19) O1 0.054(6) 0.047(5) 0.030(5) 0.003(4) 0.009(5) 0.013(5) O2 0.036(6) 0.058(6) 0.069(7) 0.022(5) -0.006(5) 0.014(5) O3 0.083(7) 0.044(5) 0.041(6) -0.003(5) -0.018(6) 0.000(5) F1 0.093(6) 0.046(4) 0.045(5) -0.010(4) 0.019(5) 0.002(5) F2 0.110(7) 0.057(5) 0.047(5) 0.025(4) 0.029(5) 0.008(5) P1' 0.062(3) 0.038(2) 0.040(2) -0.0007(19) 0.000(2) 0.008(2) O1' 0.083(8) 0.060(6) 0.063(7) 0.008(5) -0.009(7) 0.020(6) O2' 0.044(6) 0.095(8) 0.051(6) -0.014(6) 0.000(5) 0.005(6) O3' 0.107(8) 0.039(5) 0.052(6) -0.001(5) -0.053(6) 0.011(6) F1' 0.183(11) 0.059(5) 0.075(6) 0.024(5) 0.054(7) 0.022(6) F2' 0.097(7) 0.077(6) 0.073(6) -0.024(5) 0.009(6) 0.003(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 P1 O1 1.472(8) . ? P1 C1 1.812(8) . ? P1 C14 1.824(9) . ? P1 C15 1.819(12) . ? O2 C2A 1.393(11) . ? O2 C7 1.422(10) . ? O3 C3A 1.393(10) . ? O3 C8 1.427(10) . ? F1 C13 1.350(11) . ? F2 C2 1.365(11) . ? C1 C6 1.375(13) . ? C1 C2 1.415(14) . ? C2 C3 1.361(15) . ? C3 C4 1.347(15) . ? C4 C5 1.413(16) . ? C5 C6 1.398(15) . ? C6 C7 1.540(14) . ? C7 C8 1.519(14) . ? C8 C9 1.479(14) . ? C9 C14 1.375(13) . ? C9 C10 1.404(15) . ? C10 C11 1.382(15) . ? C11 C12 1.355(15) . ? C12 C13 1.405(15) . ? C13 C14 1.412(15) . ? C15 C16 1.512(19) . ? C16 C17 1.50(2) . ? P1' O1' 1.475(8) . ? P1' C15' 1.802(14) . ? P1' C14' 1.823(9) . ? P1' C1' 1.821(9) . ? O2' C7' 1.419(10) . ? O2' C2A' 1.394(11) . ? O3' C3A' 1.380(10) . ? O3' C8' 1.417(9) . ? F1' C13' 1.360(12) . ? F2' C2' 1.361(12) . ? C1' C2' 1.401(14) . ? C1' C6' 1.387(14) . ? C2' C3' 1.372(16) . ? C3' C4' 1.334(16) . ? C4' C5' 1.405(17) . ? C5' C6' 1.403(16) . ? C6' C7' 1.547(15) . ? C7' C8' 1.516(14) . ? C8' C9' 1.491(14) . ? C9' C14' 1.397(14) . ? C9' C10' 1.402(15) . ? C10' C11' 1.390(15) . ? C11' C12' 1.367(16) . ? C12' C13' 1.389(17) . ? C13' C14' 1.389(17) . ? C15' C16' 1.45(2) . ? C16' C17' 1.51(2) . ? 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 110.2(5) . . ? O1 P1 C14 110.2(5) . . ? C1 P1 C14 112.9(5) . . ? O1 P1 C15 115.9(6) . . ? C1 P1 C15 105.0(6) . . ? C14 P1 C15 102.3(6) . . ? C2A O2 C7 114.2(11) . . ? C3A O3 C8 115.1(10) . . ? C6 C1 C2 114.6(9) . . ? C6 C1 P1 127.2(8) . . ? C2 C1 P1 118.1(8) . . ? C3 C2 F2 117.5(11) . . ? C3 C2 C1 125.1(10) . . ? F2 C2 C1 117.3(10) . . ? C2 C3 C4 119.4(13) . . ? C5 C4 C3 118.8(14) . . ? C4 C5 C6 120.6(12) . . ? C1 C6 C5 121.4(11) . . ? C1 C6 C7 124.0(10) . . ? C5 C6 C7 114.6(10) . . ? O2 C7 C6 110.0(9) . . ? O2 C7 C8 107.5(9) . . ? C6 C7 C8 113.0(10) . . ? O3 C8 C9 108.4(9) . . ? O3 C8 C7 112.8(9) . . ? C9 C8 C7 116.9(10) . . ? C14 C9 C10 119.4(11) . . ? C14 C9 C8 123.8(11) . . ? C10 C9 C8 116.8(11) . . ? C11 C10 C9 123.1(13) . . ? C10 C11 C12 118.7(14) . . ? C11 C12 C13 118.7(13) . . ? F1 C13 C12 115.3(11) . . ? F1 C13 C14 121.2(10) . . ? C12 C13 C14 123.4(11) . . ? C9 C14 C13 116.4(9) . . ? C9 C14 P1 132.1(9) . . ? C13 C14 P1 111.5(8) . . ? C16 C15 P1 116.1(10) . . ? C15 C16 C17 112.1(14) . . ? O1' P1' C15' 113.8(6) . . ? O1' P1' C14' 111.9(6) . . ? C15' P1' C14' 101.4(7) . . ? O1' P1' C1' 110.9(6) . . ? C15' P1' C1' 105.0(7) . . ? C14' P1' C1' 113.3(6) . . ? C7' O2' C2A' 112.6(12) . . ? C3A' O3' C8' 117.0(10) . . ? C2' C1' C6' 113.9(10) . . ? C2' C1' P1' 118.8(9) . . ? C6' C1' P1' 126.9(9) . . ? C1' C2' C3' 125.2(12) . . ? C1' C2' F2' 116.2(11) . . ? C3' C2' F2' 118.6(12) . . ? C4' C3' C2' 119.6(16) . . ? C5' C4' C3' 119.2(18) . . ? C4' C5' C6' 120.0(15) . . ? C1' C6' C5' 121.9(12) . . ? C1' C6' C7' 123.4(11) . . ? C5' C6' C7' 114.8(11) . . ? O2' C7' C6' 109.5(10) . . ? O2' C7' C8' 106.9(9) . . ? C6' C7' C8' 114.4(11) . . ? C9' C8' O3' 108.8(9) . . ? C9' C8' C7' 115.0(11) . . ? O3' C8' C7' 108.6(9) . . ? C14' C9' C8' 126.2(11) . . ? C14' C9' C10' 120.8(11) . . ? C8' C9' C10' 113.0(11) . . ? C11' C10' C9' 120.0(14) . . ? C12' C11' C10' 121.6(16) . . ? C13' C12' C11' 116.0(16) . . ? C14' C13' C12' 126.2(12) . . ? C14' C13' F1' 118.6(11) . . ? C12' C13' F1' 115.0(13) . . ? C13' C14' C9' 115.2(10) . . ? C13' C14' P1' 114.2(8) . . ? C9' C14' P1' 130.6(9) . . ? C16' C15' P1' 118.7(11) . . ? C15' C16' C17' 117.2(14) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 21.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.359 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.069 data_m159 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 F2 O3 P' _chemical_formula_weight 400.34 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' 'F' 'F' 0.0171 0.0103 '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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 13.68(3) _cell_length_b 29.41(6) _cell_length_c 9.49(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3819(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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_type Philips PW1100 _diffrn_measurement_method _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 5 h _diffrn_standards_decay_% 0.93 _diffrn_reflns_number 2345 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.2092 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 20.99 _reflns_number_total 2345 _reflns_number_gt 1250 _reflns_threshold_expression >2sigma(I) _computing_data_collection Philips control program _computing_cell_refinement Philips control program _computing_data_reduction Philips control program _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0408P)^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 mixed _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 -0.2(4) _refine_ls_number_reflns 2345 _refine_ls_number_parameters 265 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.1442 _refine_ls_R_factor_gt 0.0840 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1517 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 0.320 _refine_ls_shift/su_mean 0.042 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 -0.4962(3) -0.02262(13) -0.6999(4) 0.0314(11) Uani 1 1 d D . . O1 O -0.4708(7) -0.0385(3) -0.5554(8) 0.050(3) Uani 1 1 d D . . O2 O -0.3097(7) -0.0795(3) -0.8328(10) 0.045(3) Uani 1 1 d D . . O3 O -0.4405(8) -0.0161(4) -1.0831(10) 0.065(4) Uani 1 1 d D . . F1 F -0.6420(6) -0.0871(3) -0.6337(9) 0.061(3) Uani 1 1 d D . . F2 F -0.4585(6) 0.0688(3) -0.6101(9) 0.065(3) Uani 1 1 d D . . C1 C -0.4003(8) 0.0142(4) -0.7719(13) 0.028(4) Uiso 1 1 d D . . C2 C -0.3911(10) 0.0571(5) -0.7118(14) 0.043(4) Uiso 1 1 d D . . C3 C -0.3209(11) 0.0884(5) -0.7496(17) 0.062(5) Uiso 1 1 d D . . H3 H -0.3199 0.1175 -0.7111 0.074 Uiso 1 1 calc R . . C4 C -0.2529(12) 0.0749(5) -0.8464(17) 0.065(6) Uiso 1 1 d D . . H4 H -0.2025 0.0945 -0.8714 0.078 Uiso 1 1 calc R . . C5 C -0.2580(11) 0.0324(5) -0.9071(16) 0.049(5) Uiso 1 1 d D . . H5 H -0.2128 0.0248 -0.9765 0.059 Uiso 1 1 calc R . . C6 C -0.3277(10) 0.0006(4) -0.8692(14) 0.033(4) Uiso 1 1 d D . . C7 C -0.3217(10) -0.0451(4) -0.9364(14) 0.041(4) Uiso 1 1 d D . . H7 H -0.2644 -0.0455 -0.9983 0.049 Uiso 1 1 calc R . . C8 C -0.4109(9) -0.0589(4) -1.0229(14) 0.032(4) Uiso 1 1 d D . . H8 H -0.3885 -0.0786 -1.0998 0.039 Uiso 1 1 calc R . . C9 C -0.4877(9) -0.0832(4) -0.9457(13) 0.030(4) Uiso 1 1 d D . . C10 C -0.5250(10) -0.1218(4) -1.0128(16) 0.048(5) Uiso 1 1 d D . . H10 H -0.5003 -0.1303 -1.1002 0.058 Uiso 1 1 calc R . . C11 C -0.5983(10) -0.1476(5) -0.9511(15) 0.047(5) Uiso 1 1 d D . . H11 H -0.6219 -0.1732 -0.9976 0.057 Uiso 1 1 calc R . . C12 C -0.6372(10) -0.1359(5) -0.8209(15) 0.049(5) Uiso 1 1 d D . . H12 H -0.6852 -0.1532 -0.7770 0.059 Uiso 1 1 calc R . . C13 C -0.6000(10) -0.0973(4) -0.7619(13) 0.035(4) Uiso 1 1 d D . . C14 C -0.5292(9) -0.0707(4) -0.8126(13) 0.032(4) Uiso 1 1 d D . . C15 C -0.6030(5) 0.0120(3) -0.7156(10) 0.031(4) Uiso 1 1 d GD . . C16 C -0.6220(6) 0.0361(3) -0.8386(8) 0.051(5) Uiso 1 1 d G . . H16 H -0.5804 0.0333 -0.9156 0.061 Uiso 1 1 calc R . . C17 C -0.7032(7) 0.0644(3) -0.8466(9) 0.059(5) Uiso 1 1 d G . . H17 H -0.7159 0.0805 -0.9289 0.071 Uiso 1 1 calc R . . C18 C -0.7654(6) 0.0686(3) -0.7315(12) 0.059(5) Uiso 1 1 d G . . H18 H -0.8197 0.0875 -0.7368 0.071 Uiso 1 1 calc R . . C19 C -0.7464(6) 0.0445(3) -0.6085(9) 0.063(5) Uiso 1 1 d G . . H19 H -0.7880 0.0473 -0.5315 0.075 Uiso 1 1 calc R . . C20 C -0.6652(7) 0.0162(3) -0.6006(8) 0.039(4) Uiso 1 1 d G . . H20 H -0.6525 0.0001 -0.5183 0.047 Uiso 1 1 calc R . . C2A C -0.2151(10) -0.0779(5) -0.7688(16) 0.063(6) Uiso 1 1 d D . . H2A1 H -0.1661 -0.0844 -0.8384 0.094 Uiso 1 1 calc R . . H2A2 H -0.2115 -0.1001 -0.6948 0.094 Uiso 1 1 calc R . . H2A3 H -0.2041 -0.0482 -0.7302 0.094 Uiso 1 1 calc R . . C3A C -0.4882(12) -0.0202(6) -1.2181(15) 0.074(6) Uiso 1 1 d D . . H3A1 H -0.4554 -0.0428 -1.2736 0.111 Uiso 1 1 calc R . . H3A2 H -0.4859 0.0085 -1.2662 0.111 Uiso 1 1 calc R . . H3A3 H -0.5551 -0.0290 -1.2043 0.111 Uiso 1 1 calc R . . P1' P -0.4196(3) -0.24578(13) -0.2559(4) 0.0326(11) Uani 1 1 d D . . O1' O -0.5086(6) -0.2285(3) -0.1839(9) 0.037(3) Uani 1 1 d D . . O2' O -0.5409(7) -0.2990(3) -0.5042(10) 0.039(3) Uani 1 1 d D . . O3' O -0.2850(8) -0.3140(3) -0.5188(11) 0.059(3) Uani 1 1 d D . . F1' F -0.4309(6) -0.1532(2) -0.3277(8) 0.046(2) Uani 1 1 d D . . F2' F -0.3801(6) -0.2949(3) 0.0006(8) 0.055(3) Uani 1 1 d D . . C1' C -0.4116(10) -0.3076(3) -0.2436(14) 0.034(4) Uiso 1 1 d D . . C2' C -0.3923(11) -0.3250(4) -0.1090(13) 0.040(4) Uiso 1 1 d D . . C3' C -0.3903(11) -0.3701(5) -0.0741(17) 0.053(5) Uiso 1 1 d D . . H3' H -0.3764 -0.3797 0.0171 0.063 Uiso 1 1 calc R . . C4' C -0.4097(11) -0.4003(6) -0.1795(16) 0.067(5) Uiso 1 1 d D . . H4' H -0.4096 -0.4313 -0.1605 0.080 Uiso 1 1 calc R . . C5' C -0.4298(11) -0.3849(5) -0.3160(18) 0.065(5) Uiso 1 1 d D . . H5' H -0.4434 -0.4060 -0.3864 0.078 Uiso 1 1 calc R . . C6' C -0.4299(11) -0.3397(5) -0.3481(14) 0.046(5) Uiso 1 1 d D . . C7' C -0.4547(10) -0.3268(5) -0.4958(14) 0.040(4) Uiso 1 1 d D . . H7' H -0.4663 -0.3547 -0.5498 0.048 Uiso 1 1 calc R . . C8' C -0.3766(10) -0.2983(4) -0.5738(17) 0.046(5) Uiso 1 1 d D . . H8' H -0.3791 -0.3066 -0.6737 0.055 Uiso 1 1 calc R . . C9' C -0.3882(10) -0.2481(4) -0.5647(13) 0.033(4) Uiso 1 1 d D . . C10' C -0.3830(11) -0.2234(5) -0.6896(16) 0.048(5) Uiso 1 1 d D . . H10' H -0.3691 -0.2386 -0.7733 0.057 Uiso 1 1 calc R . . C11' C -0.3981(10) -0.1767(5) -0.6924(16) 0.046(4) Uiso 1 1 d D . . H11' H -0.3980 -0.1614 -0.7782 0.055 Uiso 1 1 calc R . . C12' C -0.4134(11) -0.1525(5) -0.5685(14) 0.045(4) Uiso 1 1 d D . . H12' H -0.4214 -0.1211 -0.5671 0.054 Uiso 1 1 calc R . . C13' C -0.4159(11) -0.1787(4) -0.4471(13) 0.041(4) Uiso 1 1 d D . . C14' C -0.4068(10) -0.2235(4) -0.4358(10) 0.029(4) Uiso 1 1 d D . . C15' C -0.3074(5) -0.2270(3) -0.1792(10) 0.033(4) Uiso 1 1 d GD . . C16' C -0.2174(7) -0.2418(3) -0.2296(8) 0.055(5) Uiso 1 1 d G . . H16' H -0.2145 -0.2605 -0.3085 0.066 Uiso 1 1 calc R . . C17' C -0.1318(5) -0.2287(3) -0.1619(11) 0.054(5) Uiso 1 1 d G . . H17' H -0.0717 -0.2386 -0.1956 0.065 Uiso 1 1 calc R . . C18' C -0.1362(6) -0.2008(3) -0.0440(10) 0.060(5) Uiso 1 1 d G . . H18' H -0.0789 -0.1920 0.0013 0.072 Uiso 1 1 calc R . . C19' C -0.2261(8) -0.1859(3) 0.0064(8) 0.059(5) Uiso 1 1 d G . . H19' H -0.2290 -0.1673 0.0854 0.071 Uiso 1 1 calc R . . C20' C -0.3117(6) -0.1991(3) -0.0612(11) 0.059(5) Uiso 1 1 d G . . H20' H -0.3719 -0.1891 -0.0275 0.071 Uiso 1 1 calc R . . C2A' C -0.6255(10) -0.3233(5) -0.4588(17) 0.064(5) Uiso 1 1 d D . . H2A4 H -0.6292 -0.3518 -0.5079 0.096 Uiso 1 1 calc R . . H2A5 H -0.6829 -0.3057 -0.4787 0.096 Uiso 1 1 calc R . . H2A6 H -0.6213 -0.3288 -0.3593 0.096 Uiso 1 1 calc R . . C3A' C -0.2040(12) -0.3060(6) -0.6113(19) 0.095(7) Uiso 1 1 d D . . H3A4 H -0.2170 -0.3195 -0.7013 0.142 Uiso 1 1 calc R . . H3A5 H -0.1460 -0.3191 -0.5717 0.142 Uiso 1 1 calc R . . H3A6 H -0.1948 -0.2738 -0.6227 0.142 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 0.031(2) 0.035(2) 0.028(2) -0.002(2) -0.003(2) 0.000(2) O1 0.067(8) 0.054(7) 0.030(6) 0.000(6) -0.008(6) 0.004(6) O2 0.040(7) 0.058(7) 0.035(7) 0.014(6) -0.010(6) 0.004(6) O3 0.092(9) 0.081(9) 0.020(6) 0.002(6) -0.016(7) 0.018(8) F1 0.055(6) 0.072(6) 0.057(6) 0.005(5) 0.012(6) -0.014(5) F2 0.048(6) 0.078(7) 0.070(7) -0.029(6) 0.010(6) -0.012(5) P1' 0.039(3) 0.034(2) 0.024(2) 0.001(2) 0.000(2) 0.002(2) O1' 0.025(6) 0.052(6) 0.033(6) -0.002(6) 0.004(6) 0.009(5) O2' 0.040(6) 0.047(7) 0.031(6) 0.003(6) 0.008(6) -0.013(6) O3' 0.059(7) 0.060(8) 0.058(8) -0.004(7) 0.027(7) 0.007(6) F1' 0.078(7) 0.033(5) 0.027(5) -0.008(4) -0.001(5) 0.006(5) F2' 0.082(7) 0.057(6) 0.026(5) 0.014(5) 0.003(5) -0.010(6) _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 1.489(8) . ? P1 C15 1.787(7) . ? P1 C14 1.830(9) . ? P1 C1 1.834(9) . ? O2 C7 1.422(12) . ? O2 C2A 1.431(12) . ? O3 C8 1.442(12) . ? O3 C3A 1.443(13) . ? F1 C13 1.379(10) . ? F2 C2 1.379(10) . ? C1 C2 1.390(14) . ? C1 C6 1.413(14) . ? C2 C3 1.379(15) . ? C3 C4 1.367(16) . ? C4 C5 1.378(16) . ? C5 C6 1.384(14) . ? C6 C7 1.489(13) . ? C7 C8 1.527(15) . ? C8 C9 1.466(13) . ? C9 C10 1.399(14) . ? C9 C14 1.433(14) . ? C10 C11 1.388(15) . ? C11 C12 1.388(15) . ? C12 C13 1.365(15) . ? C13 C14 1.333(14) . ? C15 C16 1.3900 . ? C15 C20 1.3900 . ? C16 C17 1.3900 . ? C17 C18 1.3900 . ? C18 C19 1.3900 . ? C19 C20 1.3900 . ? P1' O1' 1.485(8) . ? P1' C15' 1.788(7) . ? P1' C1' 1.826(9) . ? P1' C14' 1.837(9) . ? O2' C7' 1.436(12) . ? O2' C2A' 1.428(12) . ? O3' C3A' 1.433(13) . ? O3' C8' 1.434(12) . ? F1' C13' 1.375(10) . ? F2' C2' 1.375(10) . ? C1' C6' 1.392(15) . ? C1' C2' 1.401(15) . ? C2' C3' 1.366(15) . ? C3' C4' 1.364(16) . ? C4' C5' 1.399(17) . ? C5' C6' 1.364(15) . ? C6' C7' 1.492(14) . ? C7' C8' 1.548(15) . ? C8' C9' 1.487(14) . ? C9' C10' 1.391(15) . ? C9' C14' 1.443(14) . ? C10' C11' 1.391(15) . ? C11' C12' 1.390(15) . ? C12' C13' 1.387(16) . ? C13' C14' 1.328(14) . ? C15' C16' 1.3900 . ? C15' C20' 1.3900 . ? C16' C17' 1.3900 . ? C17' C18' 1.3900 . ? C18' C19' 1.3900 . ? C19' C20' 1.3900 . ? 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 C15 116.5(6) . . ? O1 P1 C14 110.6(6) . . ? C15 P1 C14 101.0(5) . . ? O1 P1 C1 111.2(6) . . ? C15 P1 C1 102.5(5) . . ? C14 P1 C1 114.5(6) . . ? C7 O2 C2A 112.0(11) . . ? C8 O3 C3A 114.0(12) . . ? C2 C1 C6 117.5(10) . . ? C2 C1 P1 116.6(9) . . ? C6 C1 P1 125.4(9) . . ? F2 C2 C1 117.0(11) . . ? F2 C2 C3 118.7(13) . . ? C1 C2 C3 124.2(12) . . ? C4 C3 C2 117.1(15) . . ? C5 C4 C3 120.7(17) . . ? C4 C5 C6 122.6(15) . . ? C1 C6 C5 117.6(12) . . ? C1 C6 C7 125.0(13) . . ? C5 C6 C7 117.4(13) . . ? O2 C7 C6 110.7(11) . . ? O2 C7 C8 105.9(10) . . ? C6 C7 C8 115.2(12) . . ? O3 C8 C9 115.0(11) . . ? O3 C8 C7 101.8(10) . . ? C9 C8 C7 115.8(11) . . ? C10 C9 C14 117.7(11) . . ? C10 C9 C8 115.4(12) . . ? C14 C9 C8 126.8(12) . . ? C11 C10 C9 121.0(14) . . ? C12 C11 C10 121.1(15) . . ? C13 C12 C11 115.4(14) . . ? C12 C13 C14 127.6(12) . . ? C12 C13 F1 112.8(12) . . ? C14 C13 F1 119.6(11) . . ? C13 C14 C9 117.1(10) . . ? C13 C14 P1 114.9(9) . . ? C9 C14 P1 128.0(10) . . ? C16 C15 C20 120.0 . . ? C16 C15 P1 120.9(6) . . ? C20 C15 P1 119.0(6) . . ? C17 C16 C15 120.0 . . ? C16 C17 C18 120.0 . . ? C19 C18 C17 120.0 . . ? C20 C19 C18 120.0 . . ? C19 C20 C15 120.0 . . ? O1' P1' C15' 114.3(5) . . ? O1' P1' C1' 111.1(6) . . ? C15' P1' C1' 103.3(6) . . ? O1' P1' C14' 112.6(6) . . ? C15' P1' C14' 100.8(6) . . ? C1' P1' C14' 114.1(6) . . ? C7' O2' C2A' 111.3(10) . . ? C3A' O3' C8' 113.5(12) . . ? C6' C1' C2' 115.8(10) . . ? C6' C1' P1' 128.2(10) . . ? C2' C1' P1' 115.8(9) . . ? C3' C2' F2' 116.0(12) . . ? C3' C2' C1' 125.4(12) . . ? F2' C2' C1' 118.4(11) . . ? C4' C3' C2' 116.8(15) . . ? C3' C4' C5' 120.4(16) . . ? C6' C5' C4' 121.5(16) . . ? C5' C6' C1' 120.1(13) . . ? C5' C6' C7' 117.3(13) . . ? C1' C6' C7' 122.5(13) . . ? O2' C7' C6' 112.6(11) . . ? O2' C7' C8' 103.3(10) . . ? C6' C7' C8' 115.5(13) . . ? O3' C8' C9' 113.1(12) . . ? O3' C8' C7' 104.7(11) . . ? C9' C8' C7' 115.9(12) . . ? C10' C9' C14' 118.1(12) . . ? C10' C9' C8' 117.5(12) . . ? C14' C9' C8' 124.4(12) . . ? C11' C10' C9' 121.5(14) . . ? C10' C11' C12' 120.8(15) . . ? C13' C12' C11' 114.9(13) . . ? C14' C13' F1' 119.4(11) . . ? C14' C13' C12' 128.1(12) . . ? F1' C13' C12' 112.5(11) . . ? C13' C14' C9' 116.4(10) . . ? C13' C14' P1' 114.8(9) . . ? C9' C14' P1' 128.8(9) . . ? C16' C15' C20' 120.0 . . ? C16' C15' P1' 121.6(7) . . ? C20' C15' P1' 118.3(6) . . ? C15' C16' C17' 120.0 . . ? C18' C17' C16' 120.0 . . ? C19' C18' C17' 120.0 . . ? C20' C19' C18' 120.0 . . ? C19' C20' C15' 120.0 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 20.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.307 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.072 data_m145 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 Cl3 O3 P' _chemical_formula_weight 455.67 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' 'Cl' 'Cl' 0.1484 0.1585 '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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 12.60(2) _cell_length_b 17.44(4) _cell_length_c 9.36(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2057(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.543 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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_type Philips PW1100 _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 5 h _diffrn_standards_decay_% 1.21 _diffrn_reflns_number 1290 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1852 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 20.97 _reflns_number_total 1287 _reflns_number_gt 728 _reflns_threshold_expression >2sigma(I) _computing_data_collection Philips control program _computing_cell_refinement Philips control program _computing_data_reduction Philips control program _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0551P)^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 mixed _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 0.1(4) _refine_ls_number_reflns 1287 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1352 _refine_ls_R_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.1756 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.100 _refine_ls_shift/su_mean 0.010 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 P P -0.2136(3) -0.22055(18) -0.0319(4) 0.0314(9) Uani 1 1 d . . . O1 O -0.2876(6) -0.1549(4) -0.0083(9) 0.044(3) Uani 1 1 d . . . O2 O 0.0186(5) -0.4158(4) 0.0374(9) 0.036(2) Uani 1 1 d . . . O3 O -0.0800(7) -0.4351(5) -0.2078(10) 0.063(3) Uani 1 1 d . . . C1 C -0.2742(9) -0.2948(6) -0.1388(12) 0.026(3) Uiso 1 1 d . . . C2 C -0.3653(9) -0.2724(7) -0.2112(13) 0.042(4) Uiso 1 1 d . . . H2 H -0.3881 -0.2218 -0.2036 0.050 Uiso 1 1 calc R . . C3 C -0.4227(10) -0.3223(7) -0.2933(14) 0.045(4) Uiso 1 1 d . . . H3 H -0.4818 -0.3050 -0.3434 0.054 Uiso 1 1 calc R . . C4 C -0.3929(10) -0.3979(7) -0.3018(15) 0.052(4) Uiso 1 1 d . . . H4 H -0.4340 -0.4326 -0.3532 0.063 Uiso 1 1 calc R . . C5 C -0.3010(9) -0.4224(7) -0.2331(12) 0.039(4) Uiso 1 1 d . . . H5 H -0.2788 -0.4729 -0.2438 0.046 Uiso 1 1 calc R . . C6 C -0.2412(9) -0.3721(7) -0.1478(12) 0.030(3) Uiso 1 1 d . . . C7 C -0.1415(9) -0.4072(7) -0.0847(12) 0.037(4) Uiso 1 1 d . . . C8 C -0.0645(9) -0.3627(6) 0.0061(12) 0.027(3) Uiso 1 1 d . . . C9 C -0.1130(9) -0.3305(6) 0.1390(12) 0.029(3) Uiso 1 1 d . . . C10 C -0.0946(9) -0.3659(7) 0.2743(13) 0.035(4) Uiso 1 1 d . . . H10 H -0.0518 -0.4092 0.2814 0.042 Uiso 1 1 calc R . . C11 C -0.1407(10) -0.3353(7) 0.3921(15) 0.053(4) Uiso 1 1 d . . . H11 H -0.1308 -0.3599 0.4792 0.064 Uiso 1 1 calc R . . C12 C -0.2002(10) -0.2708(7) 0.3894(14) 0.051(4) Uiso 1 1 d . . . H12 H -0.2283 -0.2511 0.4736 0.061 Uiso 1 1 calc R . . C13 C -0.2195(10) -0.2336(7) 0.2580(12) 0.043(4) Uiso 1 1 d . . . H13 H -0.2604 -0.1893 0.2546 0.052 Uiso 1 1 calc R . . C14 C -0.1763(9) -0.2643(7) 0.1332(13) 0.034(3) Uiso 1 1 d . . . C15 C -0.0934(9) -0.1883(6) -0.1210(12) 0.026(3) Uiso 1 1 d . . . C16 C -0.0348(9) -0.1310(7) -0.0548(15) 0.040(4) Uiso 1 1 d . . . H16 H -0.0539 -0.1128 0.0350 0.049 Uiso 1 1 calc R . . C17 C 0.0512(10) -0.1020(7) -0.1242(15) 0.053(4) Uiso 1 1 d . . . H17 H 0.0885 -0.0618 -0.0825 0.063 Uiso 1 1 calc R . . C18 C 0.0845(10) -0.1295(7) -0.2516(14) 0.048(4) Uiso 1 1 d . . . H18 H 0.1446 -0.1093 -0.2954 0.058 Uiso 1 1 calc R . . C19 C 0.0283(11) -0.1878(7) -0.3156(16) 0.063(5) Uiso 1 1 d . . . H19 H 0.0502 -0.2071 -0.4034 0.075 Uiso 1 1 calc R . . C20 C -0.0604(10) -0.2176(7) -0.2496(13) 0.043(4) Uiso 1 1 d . . . H20 H -0.0978 -0.2575 -0.2921 0.051 Uiso 1 1 calc R . . Cl1 Cl -0.1189(3) -0.9248(3) -0.0543(5) 0.0829(15) Uani 1 1 d . . . Cl2 Cl -0.1563(3) -1.0010(3) 0.2110(4) 0.0786(14) Uani 1 1 d . . . Cl3 Cl -0.3291(3) -0.9272(2) 0.0656(5) 0.0789(14) Uani 1 1 d . . . C1C C -0.2118(10) -0.9752(7) 0.0444(15) 0.052(4) Uiso 1 1 d . . . HC H -0.2272 -1.0227 -0.0073 0.062 Uiso 1 1 calc R . . H2O H 0.1045 -0.4018 0.0595 0.062 Uiso 1 1 d . . . H3O H -0.1049 -0.4833 -0.1785 0.062 Uiso 1 1 d . . . H7 H -0.1639 -0.4592 -0.0157 0.062 Uiso 1 1 d . . . H8 H -0.0364 -0.3169 -0.0543 0.062 Uiso 1 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 P 0.038(2) 0.0293(18) 0.0266(18) -0.0016(19) -0.001(2) 0.004(2) O1 0.048(5) 0.034(5) 0.051(6) 0.007(5) -0.008(5) 0.015(5) O2 0.031(4) 0.029(5) 0.048(5) 0.013(5) 0.006(5) 0.006(4) O3 0.064(6) 0.063(6) 0.061(6) -0.026(6) 0.010(6) 0.017(6) Cl1 0.078(3) 0.094(3) 0.076(3) 0.013(3) 0.012(3) -0.008(3) Cl2 0.080(3) 0.114(3) 0.041(2) -0.009(3) -0.005(3) -0.002(3) Cl3 0.067(3) 0.071(3) 0.099(3) -0.015(3) -0.002(3) 0.012(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 P O1 1.493(8) . ? P C14 1.787(12) . ? P C15 1.818(12) . ? P C1 1.806(11) . ? O2 C8 1.429(12) . ? O3 C7 1.472(14) . ? C1 C2 1.389(15) . ? C1 C6 1.413(15) . ? C2 C3 1.367(15) . ? C3 C4 1.374(16) . ? C4 C5 1.391(16) . ? C5 C6 1.406(15) . ? C6 C7 1.517(15) . ? C7 C8 1.504(15) . ? C8 C9 1.496(15) . ? C9 C10 1.429(15) . ? C9 C14 1.403(15) . ? C10 C11 1.357(16) . ? C11 C12 1.351(16) . ? C12 C13 1.412(16) . ? C13 C14 1.396(16) . ? C15 C20 1.373(16) . ? C15 C16 1.390(15) . ? C16 C17 1.360(16) . ? C17 C18 1.353(17) . ? C18 C19 1.376(17) . ? C19 C20 1.379(16) . ? Cl1 C1C 1.730(13) . ? Cl2 C1C 1.768(14) . ? Cl3 C1C 1.710(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 O1 P C14 111.3(5) . . ? O1 P C15 110.6(5) . . ? C14 P C15 108.0(5) . . ? O1 P C1 111.6(5) . . ? C14 P C1 106.5(5) . . ? C15 P C1 108.6(5) . . ? C2 C1 C6 118.9(11) . . ? C2 C1 P 114.7(9) . . ? C6 C1 P 126.3(9) . . ? C1 C2 C3 122.1(12) . . ? C4 C3 C2 119.9(13) . . ? C5 C4 C3 119.7(13) . . ? C4 C5 C6 121.2(12) . . ? C1 C6 C5 118.1(11) . . ? C1 C6 C7 127.3(11) . . ? C5 C6 C7 114.5(10) . . ? O3 C7 C6 105.3(9) . . ? O3 C7 C8 105.9(9) . . ? C6 C7 C8 123.1(10) . . ? O2 C8 C9 111.8(9) . . ? O2 C8 C7 104.7(9) . . ? C9 C8 C7 113.6(9) . . ? C10 C9 C14 118.8(11) . . ? C10 C9 C8 120.6(10) . . ? C14 C9 C8 120.6(10) . . ? C9 C10 C11 118.8(11) . . ? C12 C11 C10 123.4(13) . . ? C11 C12 C13 119.6(13) . . ? C12 C13 C14 119.1(11) . . ? C13 C14 C9 120.3(11) . . ? C13 C14 P 117.2(9) . . ? C9 C14 P 122.3(9) . . ? C20 C15 C16 119.9(11) . . ? C20 C15 P 122.7(9) . . ? C16 C15 P 117.4(9) . . ? C15 C16 C17 118.5(13) . . ? C18 C17 C16 122.5(13) . . ? C19 C18 C17 119.1(13) . . ? C18 C19 C20 120.0(14) . . ? C15 C20 C19 119.9(12) . . ? Cl3 C1C Cl1 113.5(7) . . ? Cl3 C1C Cl2 111.3(8) . . ? Cl1 C1C Cl2 109.5(7) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 20.97 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.353 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.085