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 ; Diphenylphosphinoyl chloride as a chlorinating agent - the selective double activation of 1,2-diols ; loop_ _publ_author_name 'David Fox' 'Daniel Sejer Pedersen' 'Asger B. Petersen' 'Stuart Warren' data_sw0410 _database_code_depnum_ccdc_archive 'CCDC 600429' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H30 Cl O4 P' _chemical_formula_sum 'C27 H30 Cl O4 P' _chemical_formula_weight 484.93 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 5.8203(10) _cell_length_b 11.4038(2) _cell_length_c 37.8022(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2509.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 45937 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.798 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _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_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 10165 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4316 _reflns_number_gt 3904 _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^)+(0.0489P)^2^+2.1385P] 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 0.02(10) _refine_ls_number_reflns 4316 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 Cl1 Cl 1.23027(18) -0.27105(9) 0.65448(3) 0.0450(3) Uani 1 1 d . . . P1 P 0.80731(14) 0.06234(8) 0.58716(2) 0.0267(2) Uani 1 1 d . . . O1 O 1.3644(8) 0.1120(3) 0.72462(11) 0.0855(14) Uani 1 1 d . . . O2 O 1.1870(4) 0.2797(2) 0.71026(7) 0.0384(6) Uani 1 1 d . . . O3 O 1.0411(4) 0.0244(2) 0.60592(6) 0.0271(5) Uani 1 1 d . . . O4 O 0.6063(4) -0.0132(2) 0.59364(7) 0.0338(6) Uani 1 1 d . . . C1 C 1.2294(8) 0.1668(4) 0.70712(10) 0.0417(10) Uani 1 1 d . . . C2 C 1.0879(7) 0.1114(4) 0.67826(10) 0.0356(9) Uani 1 1 d . . . H2A H 1.0732 0.1674 0.6584 0.043 Uiso 1 1 calc R . . H2B H 0.9317 0.0953 0.6874 0.043 Uiso 1 1 calc R . . C3 C 1.1906(6) -0.0015(3) 0.66465(9) 0.0337(8) Uani 1 1 d . . . H3A H 1.2034 -0.0576 0.6845 0.040 Uiso 1 1 calc R . . H3B H 1.3479 0.0146 0.6559 0.040 Uiso 1 1 calc R . . C4 C 1.0535(6) -0.0577(3) 0.63532(9) 0.0269(7) Uani 1 1 d . . . H4 H 0.8954 -0.0770 0.6439 0.032 Uiso 1 1 calc R . . C5 C 1.1665(6) -0.1670(3) 0.61949(9) 0.0303(8) Uani 1 1 d . . . H5 H 1.3151 -0.1427 0.6084 0.036 Uiso 1 1 calc R . . C6 C 1.0239(6) -0.2275(3) 0.59155(10) 0.0307(8) Uani 1 1 d . . . C7 C 0.8097(6) -0.2766(4) 0.60041(11) 0.0380(9) Uani 1 1 d . . . H7 H 0.7534 -0.2721 0.6240 0.046 Uiso 1 1 calc R . . C8 C 0.6830(7) -0.3313(4) 0.57447(12) 0.0444(10) Uani 1 1 d . . . H8 H 0.5378 -0.3640 0.5804 0.053 Uiso 1 1 calc R . . C9 C 0.7612(8) -0.3397(4) 0.54027(12) 0.0484(11) Uani 1 1 d . . . H9 H 0.6726 -0.3788 0.5228 0.058 Uiso 1 1 calc R . . C10 C 0.9727(8) -0.2900(4) 0.53168(11) 0.0472(11) Uani 1 1 d . . . H10 H 1.0291 -0.2947 0.5081 0.057 Uiso 1 1 calc R . . C11 C 1.1004(7) -0.2336(4) 0.55746(10) 0.0379(9) Uani 1 1 d . . . H11 H 1.2432 -0.1987 0.5514 0.046 Uiso 1 1 calc R . . C12 C 1.3018(7) 0.3536(4) 0.73719(11) 0.0448(10) Uani 1 1 d . . . C13 C 1.5622(7) 0.3477(5) 0.73273(13) 0.0570(13) Uani 1 1 d . . . H13A H 1.6019 0.3611 0.7079 0.086 Uiso 1 1 calc R . . H13B H 1.6172 0.2701 0.7400 0.086 Uiso 1 1 calc R . . H13C H 1.6345 0.4080 0.7474 0.086 Uiso 1 1 calc R . . C14 C 1.2127(10) 0.4733(4) 0.72863(16) 0.0712(16) Uani 1 1 d . . . H14A H 1.2539 0.4935 0.7042 0.107 Uiso 1 1 calc R . . H14B H 1.2807 0.5306 0.7449 0.107 Uiso 1 1 calc R . . H14C H 1.0452 0.4742 0.7312 0.107 Uiso 1 1 calc R . . C15 C 1.2307(10) 0.3134(6) 0.77348(12) 0.0759(17) Uani 1 1 d . . . H15A H 1.0628 0.3079 0.7746 0.114 Uiso 1 1 calc R . . H15B H 1.2848 0.3699 0.7911 0.114 Uiso 1 1 calc R . . H15C H 1.2982 0.2363 0.7783 0.114 Uiso 1 1 calc R . . C16 C 0.7577(6) 0.2090(3) 0.60273(9) 0.0299(8) Uani 1 1 d . . . C17 C 0.5468(6) 0.2335(4) 0.61887(10) 0.0335(8) Uani 1 1 d . . . H17 H 0.4315 0.1747 0.6202 0.040 Uiso 1 1 calc R . . C18 C 0.5065(7) 0.3434(4) 0.63292(11) 0.0402(9) Uani 1 1 d . . . H18 H 0.3635 0.3592 0.6441 0.048 Uiso 1 1 calc R . . C19 C 0.6705(7) 0.4307(4) 0.63107(10) 0.0421(10) Uani 1 1 d . . . H19 H 0.6410 0.5054 0.6412 0.051 Uiso 1 1 calc R . . C20 C 0.8790(7) 0.4090(4) 0.61429(11) 0.0410(10) Uani 1 1 d . . . H20 H 0.9911 0.4692 0.6124 0.049 Uiso 1 1 calc R . . C21 C 0.9212(6) 0.2993(3) 0.60045(10) 0.0339(9) Uani 1 1 d . . . H21 H 1.0640 0.2844 0.5891 0.041 Uiso 1 1 calc R . . C22 C 0.8873(6) 0.0736(3) 0.54154(9) 0.0285(8) Uani 1 1 d . . . C23 C 0.7262(6) 0.0433(3) 0.51603(9) 0.0338(8) Uani 1 1 d . . . H23 H 0.5828 0.0111 0.5231 0.041 Uiso 1 1 calc R . . C24 C 0.7715(7) 0.0593(4) 0.48067(10) 0.0375(9) Uani 1 1 d . . . H24 H 0.6609 0.0368 0.4635 0.045 Uiso 1 1 calc R . . C25 C 1.1010(6) 0.1192(3) 0.53053(10) 0.0308(8) Uani 1 1 d . . . H25 H 1.2156 0.1376 0.5475 0.037 Uiso 1 1 calc R . . C26 C 1.1430(7) 0.1371(3) 0.49531(10) 0.0352(9) Uani 1 1 d . . . H26 H 1.2858 0.1694 0.4880 0.042 Uiso 1 1 calc R . . C27 C 0.9788(6) 0.1083(3) 0.47005(10) 0.0349(9) Uani 1 1 d . . . H27 H 1.0082 0.1220 0.4457 0.042 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 Cl1 0.0486(6) 0.0338(5) 0.0525(6) 0.0107(4) -0.0064(5) 0.0069(5) P1 0.0168(4) 0.0272(5) 0.0361(5) 0.0031(4) -0.0001(4) -0.0009(4) O1 0.117(3) 0.057(2) 0.083(3) -0.002(2) -0.066(3) 0.011(2) O2 0.0305(13) 0.0397(16) 0.0452(15) -0.0103(12) -0.0060(12) -0.0014(13) O3 0.0164(11) 0.0254(13) 0.0395(13) 0.0076(10) -0.0024(10) 0.0019(10) O4 0.0186(11) 0.0315(14) 0.0512(16) 0.0054(12) 0.0033(11) -0.0062(10) C1 0.048(2) 0.040(2) 0.037(2) 0.0025(18) -0.0101(19) -0.004(2) C2 0.036(2) 0.033(2) 0.038(2) 0.0005(17) -0.0058(17) -0.0036(18) C3 0.0289(19) 0.034(2) 0.0380(19) 0.0030(16) -0.0036(16) -0.0019(18) C4 0.0248(16) 0.0184(17) 0.0375(19) 0.0070(15) -0.0008(14) -0.0017(15) C5 0.0268(18) 0.0207(18) 0.043(2) 0.0079(15) -0.0014(15) -0.0013(15) C6 0.0234(17) 0.0217(18) 0.047(2) 0.0026(17) -0.0002(15) 0.0015(15) C7 0.0285(18) 0.034(2) 0.052(2) 0.0023(18) 0.0052(17) -0.0025(18) C8 0.034(2) 0.030(2) 0.069(3) 0.0026(19) -0.008(2) -0.0001(19) C9 0.057(3) 0.031(2) 0.058(3) 0.0023(19) -0.019(2) -0.005(2) C10 0.063(3) 0.037(2) 0.042(2) -0.0016(19) -0.002(2) -0.002(2) C11 0.034(2) 0.032(2) 0.048(2) 0.0013(18) 0.0032(18) 0.0021(18) C12 0.034(2) 0.054(3) 0.046(2) -0.020(2) -0.0025(19) -0.004(2) C13 0.031(2) 0.073(4) 0.067(3) -0.023(3) -0.004(2) -0.006(2) C14 0.061(3) 0.047(3) 0.105(4) -0.033(3) -0.023(3) 0.003(3) C15 0.067(3) 0.114(5) 0.047(3) -0.029(3) 0.005(2) -0.020(3) C16 0.0247(18) 0.0314(19) 0.0336(18) 0.0043(15) -0.0015(14) 0.0002(16) C17 0.0255(18) 0.036(2) 0.039(2) 0.0020(18) 0.0035(15) 0.0023(17) C18 0.034(2) 0.043(2) 0.044(2) 0.0000(19) 0.0087(18) 0.0061(19) C19 0.049(2) 0.033(2) 0.044(2) -0.0029(18) 0.0034(19) 0.009(2) C20 0.037(2) 0.028(2) 0.058(3) 0.0008(18) -0.0031(19) -0.0040(17) C21 0.0222(17) 0.031(2) 0.048(2) 0.0004(17) 0.0009(16) -0.0006(16) C22 0.0198(16) 0.0248(19) 0.041(2) 0.0034(16) 0.0005(14) 0.0019(14) C23 0.0229(17) 0.035(2) 0.043(2) -0.0019(16) -0.0031(16) -0.0026(16) C24 0.033(2) 0.037(2) 0.042(2) -0.0031(17) -0.0073(17) -0.0001(19) C25 0.0230(17) 0.029(2) 0.041(2) -0.0037(16) -0.0029(15) -0.0035(15) C26 0.030(2) 0.032(2) 0.044(2) 0.0000(17) 0.0069(17) 0.0023(16) C27 0.036(2) 0.031(2) 0.037(2) 0.0013(17) 0.0040(17) 0.0067(17) _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 Cl1 C5 1.815(3) . ? P1 O4 1.473(2) . ? P1 O3 1.595(2) . ? P1 C22 1.791(4) . ? P1 C16 1.796(4) . ? O1 C1 1.203(5) . ? O2 C1 1.316(5) . ? O2 C12 1.481(5) . ? O3 C4 1.455(4) . ? C1 C2 1.506(5) . ? C2 C3 1.509(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.510(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.530(5) . ? C4 H4 1.0000 . ? C5 C6 1.510(5) . ? C5 H5 1.0000 . ? C6 C11 1.365(5) . ? C6 C7 1.407(5) . ? C7 C8 1.376(6) . ? C7 H7 0.9500 . ? C8 C9 1.374(6) . ? C8 H8 0.9500 . ? C9 C10 1.394(6) . ? C9 H9 0.9500 . ? C10 C11 1.384(6) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C14 1.496(7) . ? C12 C15 1.504(7) . ? C12 C13 1.526(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.399(5) . ? C16 C21 1.405(5) . ? C17 C18 1.381(6) . ? C17 H17 0.9500 . ? C18 C19 1.381(6) . ? C18 H18 0.9500 . ? C19 C20 1.391(6) . ? C19 H19 0.9500 . ? C20 C21 1.378(6) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.389(5) . ? C22 C25 1.411(5) . ? C23 C24 1.375(5) . ? C23 H23 0.9500 . ? C24 C27 1.389(6) . ? C24 H24 0.9500 . ? C25 C26 1.369(5) . ? C25 H25 0.9500 . ? C26 C27 1.390(6) . ? C26 H26 0.9500 . ? C27 H27 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 116.41(14) . . ? O4 P1 C22 114.11(16) . . ? O3 P1 C22 103.06(15) . . ? O4 P1 C16 111.24(16) . . ? O3 P1 C16 104.13(15) . . ? C22 P1 C16 106.90(16) . . ? C1 O2 C12 122.3(3) . . ? C4 O3 P1 123.8(2) . . ? O1 C1 O2 125.6(4) . . ? O1 C1 C2 122.5(4) . . ? O2 C1 C2 111.9(3) . . ? C1 C2 C3 112.9(3) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 113.8(3) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? O3 C4 C3 108.3(3) . . ? O3 C4 C5 104.3(3) . . ? C3 C4 C5 114.0(3) . . ? O3 C4 H4 110.0 . . ? C3 C4 H4 110.0 . . ? C5 C4 H4 110.0 . . ? C6 C5 C4 114.2(3) . . ? C6 C5 Cl1 108.9(2) . . ? C4 C5 Cl1 109.6(2) . . ? C6 C5 H5 108.0 . . ? C4 C5 H5 108.0 . . ? Cl1 C5 H5 108.0 . . ? C11 C6 C7 119.6(4) . . ? C11 C6 C5 120.3(3) . . ? C7 C6 C5 120.1(3) . . ? C8 C7 C6 119.0(4) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 C7 121.7(4) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 118.9(4) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 119.9(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C6 C11 C10 120.9(4) . . ? C6 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? O2 C12 C14 102.4(3) . . ? O2 C12 C15 109.3(4) . . ? C14 C12 C15 112.3(4) . . ? O2 C12 C13 110.3(3) . . ? C14 C12 C13 111.1(5) . . ? C15 C12 C13 111.1(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 118.3(3) . . ? C17 C16 P1 118.0(3) . . ? C21 C16 P1 123.6(3) . . ? C18 C17 C16 119.9(4) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 121.1(4) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C20 119.8(4) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C21 C20 C19 119.4(4) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C16 121.4(3) . . ? C20 C21 H21 119.3 . . ? C16 C21 H21 119.3 . . ? C23 C22 C25 118.8(3) . . ? C23 C22 P1 118.4(3) . . ? C25 C22 P1 122.7(3) . . ? C24 C23 C22 120.8(4) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C27 120.1(4) . . ? C23 C24 H24 120.0 . . ? C27 C24 H24 120.0 . . ? C26 C25 C22 119.9(3) . . ? C26 C25 H25 120.0 . . ? C22 C25 H25 120.0 . . ? C25 C26 C27 120.7(4) . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C24 C27 C26 119.6(4) . . ? C24 C27 H27 120.2 . . ? C26 C27 H27 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 -16.9(3) . . . . ? C22 P1 O3 C4 -142.6(3) . . . . ? C16 P1 O3 C4 105.9(3) . . . . ? C12 O2 C1 O1 -1.3(7) . . . . ? C12 O2 C1 C2 179.0(3) . . . . ? O1 C1 C2 C3 -21.4(6) . . . . ? O2 C1 C2 C3 158.2(3) . . . . ? C1 C2 C3 C4 -179.1(3) . . . . ? P1 O3 C4 C3 -128.2(3) . . . . ? P1 O3 C4 C5 110.1(3) . . . . ? C2 C3 C4 O3 60.0(4) . . . . ? C2 C3 C4 C5 175.5(3) . . . . ? O3 C4 C5 C6 -65.4(3) . . . . ? C3 C4 C5 C6 176.8(3) . . . . ? O3 C4 C5 Cl1 172.2(2) . . . . ? C3 C4 C5 Cl1 54.4(3) . . . . ? C4 C5 C6 C11 115.9(4) . . . . ? Cl1 C5 C6 C11 -121.3(3) . . . . ? C4 C5 C6 C7 -63.2(4) . . . . ? Cl1 C5 C6 C7 59.5(4) . . . . ? C11 C6 C7 C8 0.8(6) . . . . ? C5 C6 C7 C8 180.0(3) . . . . ? C6 C7 C8 C9 0.5(6) . . . . ? C7 C8 C9 C10 -1.0(6) . . . . ? C8 C9 C10 C11 0.2(6) . . . . ? C7 C6 C11 C10 -1.6(6) . . . . ? C5 C6 C11 C10 179.3(4) . . . . ? C9 C10 C11 C6 1.1(6) . . . . ? C1 O2 C12 C14 175.9(4) . . . . ? C1 O2 C12 C15 -64.8(5) . . . . ? C1 O2 C12 C13 57.6(5) . . . . ? O4 P1 C16 C17 0.9(3) . . . . ? O3 P1 C16 C17 -125.3(3) . . . . ? C22 P1 C16 C17 126.0(3) . . . . ? O4 P1 C16 C21 179.1(3) . . . . ? O3 P1 C16 C21 52.9(3) . . . . ? C22 P1 C16 C21 -55.8(3) . . . . ? C21 C16 C17 C18 -1.8(5) . . . . ? P1 C16 C17 C18 176.5(3) . . . . ? C16 C17 C18 C19 0.6(6) . . . . ? C17 C18 C19 C20 1.1(6) . . . . ? C18 C19 C20 C21 -1.6(6) . . . . ? C19 C20 C21 C16 0.4(6) . . . . ? C17 C16 C21 C20 1.3(5) . . . . ? P1 C16 C21 C20 -176.9(3) . . . . ? O4 P1 C22 C23 18.8(4) . . . . ? O3 P1 C22 C23 146.0(3) . . . . ? C16 P1 C22 C23 -104.6(3) . . . . ? O4 P1 C22 C25 -165.6(3) . . . . ? O3 P1 C22 C25 -38.4(3) . . . . ? C16 P1 C22 C25 71.0(3) . . . . ? C25 C22 C23 C24 -1.2(6) . . . . ? P1 C22 C23 C24 174.6(3) . . . . ? C22 C23 C24 C27 -1.2(6) . . . . ? C23 C22 C25 C26 2.5(6) . . . . ? P1 C22 C25 C26 -173.2(3) . . . . ? C22 C25 C26 C27 -1.4(6) . . . . ? C23 C24 C27 C26 2.3(6) . . . . ? C25 C26 C27 C24 -1.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.491 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.057