# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/187 data_global _publ_contact_author_name 'Dr. Andres E. Goeta' _publ_contact_author_address ; Department of Chemistry Durham University Durham DH1 3LE UK ; _publ_contact_author_phone '+44 191 3744702' _publ_contact_author_fax '+44 191 3844737' _publ_contact_author_email A.E.Goeta@durham.ac.uk loop_ _publ_author_name 'Matthew G. Davidson' 'Andres E. Goeta' 'Judith A.K. Howard' 'Sarah Lamb' 'Sax A. Mason' _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; The Shortest C-H...O Hydrogen Bonds yet Determined by Single Crystal Neutron Diffraction: A Structural Study of two Phosphonium Aryloxides ; #============================================= data_1a _chemical_formula_sum 'C37 H31 O P' _chemical_formula_weight 522.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0000 0.0000 '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' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.430(1) _cell_length_b 13.748(1) _cell_length_c 18.444(1) _cell_angle_alpha 88.310(3) _cell_angle_beta 70.157(3) _cell_angle_gamma 62.542(3) _cell_volume 2809.2(1) _cell_formula_units_Z 4 _cell_measurement_temperature 20(2) _cell_measurement_reflns_used 5783 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 50.3 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour green _exptl_crystal_size_max 4.9 _exptl_crystal_size_mid 3.9 _exptl_crystal_size_min 1.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.234 _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.4607 _exptl_absorpt_correction_T_max 0.7844 _diffrn_ambient_temperature 20(2) _diffrn_radiation_wavelength 1.3137 _diffrn_radiation_type neutron _diffrn_source 'nuclear reactor' _diffrn_radiation_monochromator 'Ge 115' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_details ; D19 - ILL ; _diffrn_measurement_method 'omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 400 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12265 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 50.29 _reflns_number_total 8567 _reflns_number_observed 8018 _reflns_observed_criterion >2sigma(I) _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+25.6053P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00093(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 8567 _refine_ls_number_parameters 1262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_obs 0.0440 _refine_ls_wR_factor_all 0.1319 _refine_ls_wR_factor_obs 0.1264 _refine_ls_goodness_of_fit_all 1.133 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.853 _refine_diff_density_min -1.099 _refine_diff_density_rms 0.195 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 P11 P 0.4414(2) 0.5701(2) 0.69110(14) 0.0061(5) Uani 1 1 d . . . O11 O 0.7127(2) 0.43905(18) 0.45860(13) 0.0086(5) Uani 1 1 d . . . C11 C 0.46893(19) 0.58802(17) 0.59128(11) 0.0068(4) Uani 1 1 d . . . H111 H 0.3957(4) 0.5907(4) 0.5757(3) 0.0250(10) Uani 1 1 d . . . H112 H 0.5570(4) 0.5221(4) 0.5526(3) 0.0235(9) Uani 1 1 d . . . H113 H 0.4694(5) 0.6665(4) 0.5838(3) 0.0251(10) Uani 1 1 d . . . C121 C 0.30077(18) 0.68540(16) 0.74998(11) 0.0072(4) Uani 1 1 d . . . C122 C 0.23970(19) 0.67454(16) 0.82550(11) 0.0088(4) Uani 1 1 d . . . H122 H 0.2765(4) 0.5971(4) 0.8480(2) 0.0222(9) Uani 1 1 d . . . C123 C 0.12810(19) 0.76277(17) 0.87135(12) 0.0097(4) Uani 1 1 d . . . H123 H 0.0797(4) 0.7536(4) 0.9296(3) 0.0268(10) Uani 1 1 d . . . C124 C 0.0776(2) 0.86098(17) 0.84196(12) 0.0102(4) Uani 1 1 d . . . H124 H -0.0091(4) 0.9289(4) 0.8778(3) 0.0268(10) Uani 1 1 d . . . C125 C 0.13773(19) 0.87190(16) 0.76647(12) 0.0098(4) Uani 1 1 d . . . H125 H 0.0982(4) 0.9480(4) 0.7432(3) 0.0268(10) Uani 1 1 d . . . C126 C 0.24876(19) 0.78401(16) 0.72016(12) 0.0093(4) Uani 1 1 d . . . H126 H 0.2932(4) 0.7918(4) 0.6604(2) 0.0215(9) Uani 1 1 d . . . C131 C 0.56391(18) 0.55477(15) 0.71664(11) 0.0062(4) Uani 1 1 d . . . C132 C 0.54773(19) 0.59544(16) 0.79080(12) 0.0079(4) Uani 1 1 d . . . H132 H 0.4579(4) 0.6475(4) 0.8337(3) 0.0224(9) Uani 1 1 d . . . C133 C 0.64873(19) 0.56912(17) 0.80990(12) 0.0097(4) Uani 1 1 d . . . H133 H 0.6364(5) 0.6001(4) 0.8676(3) 0.0279(10) Uani 1 1 d . . . C134 C 0.76492(19) 0.50395(17) 0.75512(12) 0.0100(4) Uani 1 1 d . . . H134 H 0.8426(4) 0.4844(4) 0.7709(3) 0.0260(10) Uani 1 1 d . . . C135 C 0.78130(19) 0.46415(17) 0.68080(12) 0.0090(4) Uani 1 1 d . . . H135 H 0.8714(4) 0.4138(4) 0.6374(3) 0.0252(10) Uani 1 1 d . . . C136 C 0.68149(19) 0.48946(16) 0.66147(12) 0.0086(4) Uani 1 1 d . . . H136 H 0.6945(4) 0.4574(4) 0.6039(2) 0.0244(10) Uani 1 1 d . . . C141 C 0.43137(18) 0.44505(16) 0.70800(11) 0.0069(4) Uani 1 1 d . . . C142 C 0.36381(18) 0.42056(16) 0.67541(11) 0.0068(4) Uani 1 1 d . . . H142 H 0.3254(4) 0.4713(4) 0.6356(3) 0.0200(9) Uani 1 1 d . . . C143 C 0.34815(19) 0.32796(16) 0.69335(12) 0.0085(4) Uani 1 1 d . . . H143 H 0.2962(4) 0.3093(4) 0.6688(3) 0.0246(10) Uani 1 1 d . . . C144 C 0.40139(19) 0.25988(16) 0.74184(12) 0.0086(4) Uani 1 1 d . . . H144 H 0.3884(5) 0.1885(4) 0.7557(3) 0.0269(10) Uani 1 1 d . . . C145 C 0.47017(19) 0.28351(16) 0.77279(11) 0.0087(4) Uani 1 1 d . . . H145 H 0.5107(4) 0.2304(4) 0.8105(3) 0.0245(10) Uani 1 1 d . . . C146 C 0.48463(19) 0.37681(16) 0.75628(11) 0.0075(4) Uani 1 1 d . . . H146 H 0.5391(4) 0.3950(4) 0.7811(3) 0.0229(9) Uani 1 1 d . . . C151 C 0.82034(18) 0.38567(16) 0.45965(11) 0.0067(4) Uani 1 1 d . . . C152 C 0.89478(18) 0.43830(16) 0.44920(11) 0.0063(4) Uani 1 1 d . . . C153 C 1.01252(19) 0.37869(16) 0.44828(11) 0.0084(4) Uani 1 1 d . . . H153 H 1.0650(4) 0.4207(4) 0.4416(3) 0.0228(9) Uani 1 1 d . . . C154 C 1.0612(2) 0.26731(17) 0.45895(12) 0.0099(4) Uani 1 1 d . . . H154 H 1.1501(4) 0.2247(4) 0.4622(3) 0.0248(10) Uani 1 1 d . . . C155 C 0.99124(18) 0.21453(16) 0.46785(11) 0.0078(4) Uani 1 1 d . . . H155 H 1.0287(4) 0.1280(3) 0.4769(3) 0.0213(9) Uani 1 1 d . . . C156 C 0.87410(18) 0.26978(16) 0.46723(11) 0.0062(4) Uani 1 1 d . . . C161 C 0.80873(18) 0.20621(16) 0.47035(11) 0.0066(4) Uani 1 1 d . . . C162 C 0.87276(19) 0.09778(16) 0.43014(12) 0.0079(4) Uani 1 1 d . . . H162 H 0.9681(4) 0.0630(4) 0.3948(3) 0.0240(10) Uani 1 1 d . . . C163 C 0.81510(19) 0.03333(17) 0.43452(12) 0.0098(4) Uani 1 1 d . . . H163 H 0.8671(4) -0.0515(4) 0.4035(3) 0.0264(10) Uani 1 1 d . . . C164 C 0.69189(19) 0.07759(17) 0.47898(12) 0.0104(4) Uani 1 1 d . . . H164 H 0.6474(4) 0.0277(4) 0.4829(3) 0.0283(10) Uani 1 1 d . . . C165 C 0.6277(2) 0.18542(16) 0.51881(12) 0.0092(4) Uani 1 1 d . . . H165 H 0.5327(4) 0.2206(4) 0.5546(3) 0.0258(10) Uani 1 1 d . . . C166 C 0.68598(19) 0.24926(16) 0.51500(11) 0.0083(4) Uani 1 1 d . . . H166 H 0.6340(4) 0.3325(3) 0.5469(3) 0.0250(10) Uani 1 1 d . . . C171 C 0.84865(18) 0.55528(16) 0.43559(11) 0.0061(4) Uani 1 1 d . . . C172 C 0.73434(19) 0.64027(16) 0.48342(12) 0.0082(4) Uani 1 1 d . . . H172 H 0.6770(4) 0.6190(4) 0.5299(3) 0.0231(9) Uani 1 1 d . . . C173 C 0.69637(19) 0.75043(16) 0.47205(12) 0.0086(4) Uani 1 1 d . . . H173 H 0.6073(4) 0.8149(4) 0.5101(3) 0.0237(9) Uani 1 1 d . . . C174 C 0.7704(2) 0.77920(17) 0.41185(12) 0.0101(4) Uani 1 1 d . . . H174 H 0.7400(4) 0.8647(4) 0.4021(3) 0.0257(10) Uani 1 1 d . . . C175 C 0.8835(2) 0.69538(17) 0.36344(12) 0.0100(4) Uani 1 1 d . . . H175 H 0.9418(5) 0.7168(4) 0.3167(3) 0.0267(10) Uani 1 1 d . . . C176 C 0.92105(19) 0.58522(17) 0.37526(12) 0.0077(4) Uani 1 1 d . . . H176 H 1.0082(4) 0.5197(4) 0.3367(3) 0.0241(10) Uani 1 1 d . . . P21 P 0.7135(2) 0.9206(2) 0.81649(14) 0.0056(5) Uani 1 1 d . . . O21 O 0.3956(2) 1.17115(18) 0.95147(13) 0.0073(5) Uani 1 1 d . . . C21 C 0.64332(19) 0.97526(16) 0.91704(11) 0.0067(4) Uani 1 1 d . . . H211 H 0.6237(4) 0.9157(4) 0.9523(2) 0.0216(9) Uani 1 1 d . . . H212 H 0.5596(4) 1.0542(4) 0.9274(3) 0.0241(10) Uani 1 1 d . . . H213 H 0.7055(4) 0.9906(4) 0.9342(3) 0.0232(9) Uani 1 1 d . . . C221 C 0.84425(18) 0.78867(15) 0.80073(11) 0.0058(4) Uani 1 1 d . . . C222 C 0.95469(18) 0.76058(16) 0.74034(11) 0.0066(4) Uani 1 1 d . . . H222 H 0.9640(4) 0.8176(4) 0.7003(3) 0.0222(9) Uani 1 1 d . . . C223 C 1.05454(19) 0.65771(16) 0.73212(12) 0.0078(4) Uani 1 1 d . . . H223 H 1.1397(4) 0.6353(4) 0.6853(3) 0.0245(10) Uani 1 1 d . . . C224 C 1.04387(19) 0.58326(16) 0.78362(11) 0.0077(4) Uani 1 1 d . . . H224 H 1.1230(4) 0.5046(4) 0.7769(3) 0.0243(10) Uani 1 1 d . . . C225 C 0.93352(19) 0.61095(16) 0.84336(11) 0.0080(4) Uani 1 1 d . . . H225 H 0.9236(4) 0.5542(4) 0.8837(3) 0.0233(9) Uani 1 1 d . . . C226 C 0.83310(19) 0.71361(16) 0.85217(11) 0.0072(4) Uani 1 1 d . . . H226 H 0.7486(4) 0.7352(4) 0.8996(3) 0.0252(10) Uani 1 1 d . . . C231 C 0.75552(18) 1.01442(15) 0.76172(11) 0.0065(4) Uani 1 1 d . . . C232 C 0.76821(19) 1.01286(16) 0.68324(11) 0.0086(4) Uani 1 1 d . . . H232 H 0.7523(5) 0.9557(4) 0.6559(3) 0.0238(10) Uani 1 1 d . . . C233 C 0.80184(19) 1.08458(16) 0.63988(12) 0.0097(4) Uani 1 1 d . . . H233 H 0.8115(5) 1.0831(4) 0.5789(2) 0.0249(10) Uani 1 1 d . . . C234 C 0.82169(19) 1.15977(16) 0.67497(12) 0.0102(4) Uani 1 1 d . . . H234 H 0.8459(5) 1.2162(4) 0.6400(3) 0.0273(10) Uani 1 1 d . . . C235 C 0.8083(2) 1.16158(17) 0.75303(12) 0.0113(4) Uani 1 1 d . . . H235 H 0.8216(5) 1.2212(4) 0.7813(3) 0.0280(10) Uani 1 1 d . . . C236 C 0.77599(19) 1.08949(16) 0.79703(12) 0.0089(4) Uani 1 1 d . . . H236 H 0.7625(5) 1.0948(4) 0.8584(3) 0.0249(10) Uani 1 1 d . . . C241 C 0.61228(18) 0.90302(15) 0.78163(11) 0.0065(4) Uani 1 1 d . . . C242 C 0.65870(19) 0.81603(16) 0.72203(11) 0.0082(4) Uani 1 1 d . . . H242 H 0.7543(4) 0.7544(4) 0.7004(3) 0.0246(10) Uani 1 1 d . . . C243 C 0.58180(19) 0.80834(17) 0.68956(12) 0.0096(4) Uani 1 1 d . . . H243 H 0.6186(4) 0.7410(4) 0.6433(3) 0.0263(10) Uani 1 1 d . . . C244 C 0.4595(2) 0.88807(17) 0.71686(12) 0.0113(4) Uani 1 1 d . . . H244 H 0.4007(5) 0.8823(4) 0.6915(3) 0.0297(11) Uani 1 1 d . . . C245 C 0.41363(19) 0.97376(17) 0.77669(12) 0.0095(4) Uani 1 1 d . . . H245 H 0.3185(4) 1.0353(4) 0.7988(3) 0.0264(10) Uani 1 1 d . . . C246 C 0.48933(19) 0.98255(16) 0.80976(12) 0.0071(4) Uani 1 1 d . . . H246 H 0.4525(4) 1.0506(4) 0.8567(3) 0.0224(9) Uani 1 1 d . . . C251 C 0.33907(18) 1.27766(16) 0.95851(11) 0.0061(4) Uani 1 1 d . . . C252 C 0.22519(18) 1.33557(16) 0.94692(11) 0.0072(4) Uani 1 1 d . . . C253 C 0.16536(19) 1.45118(16) 0.95518(11) 0.0087(4) Uani 1 1 d . . . H253 H 0.0781(4) 1.4938(3) 0.9482(3) 0.0217(9) Uani 1 1 d . . . C254 C 0.21205(19) 1.51521(16) 0.97492(11) 0.0087(4) Uani 1 1 d . . . H254 H 0.1603(4) 1.6044(4) 0.9849(3) 0.0280(10) Uani 1 1 d . . . C255 C 0.32354(19) 1.46079(16) 0.98351(11) 0.0084(4) Uani 1 1 d . . . H255 H 0.3609(4) 1.5076(4) 0.9971(3) 0.0235(9) Uani 1 1 d . . . C256 C 0.38659(18) 1.34460(16) 0.97541(11) 0.0064(4) Uani 1 1 d . . . C261 C 0.50644(18) 1.29258(16) 0.98359(11) 0.0075(4) Uani 1 1 d . . . C262 C 0.59108(19) 1.32787(16) 0.94586(11) 0.0096(4) Uani 1 1 d . . . H262 H 0.5702(4) 1.3925(4) 0.9095(3) 0.0231(9) Uani 1 1 d . . . C263 C 0.70285(19) 1.28247(17) 0.95466(12) 0.0100(4) Uani 1 1 d . . . H263 H 0.7678(4) 1.3111(4) 0.9251(3) 0.0244(10) Uani 1 1 d . . . C264 C 0.7321(2) 1.20068(17) 1.00225(12) 0.0097(4) Uani 1 1 d . . . H264 H 0.8181(4) 1.1654(4) 1.0095(3) 0.0258(10) Uani 1 1 d . . . C265 C 0.64767(19) 1.16550(17) 1.04083(12) 0.0090(4) Uani 1 1 d . . . H265 H 0.6677(4) 1.1037(4) 1.0787(3) 0.0246(10) Uani 1 1 d . . . C266 C 0.53683(19) 1.21074(16) 1.03143(11) 0.0080(4) Uani 1 1 d . . . H266 H 0.4727(4) 1.1815(4) 1.0614(3) 0.0216(9) Uani 1 1 d . . . C271 C 0.17007(18) 1.27344(16) 0.92633(11) 0.0058(4) Uani 1 1 d . . . C272 C 0.17295(18) 1.17931(16) 0.95955(11) 0.0075(4) Uani 1 1 d . . . H272 H 0.2194(4) 1.1492(4) 0.9995(3) 0.0233(10) Uani 1 1 d . . . C273 C 0.11596(19) 1.12504(16) 0.94137(12) 0.0093(4) Uani 1 1 d . . . H273 H 0.1194(5) 1.0530(4) 0.9681(3) 0.0252(10) Uani 1 1 d . . . C274 C 0.0557(2) 1.16268(17) 0.88945(12) 0.0113(4) Uani 1 1 d . . . H274 H 0.0124(4) 1.1213(4) 0.8757(3) 0.0263(10) Uani 1 1 d . . . C275 C 0.05347(19) 1.25588(17) 0.85578(12) 0.0104(4) Uani 1 1 d . . . H275 H 0.0063(5) 1.2874(4) 0.8153(3) 0.0300(11) Uani 1 1 d . . . C276 C 0.11010(18) 1.30920(16) 0.87351(11) 0.0081(4) Uani 1 1 d . . . H276 H 0.1102(4) 1.3798(4) 0.8454(3) 0.0256(10) Uani 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 P11 0.0019(12) 0.0058(11) 0.0052(12) 0.0003(9) 0.0004(10) 0.0012(10) O11 0.0078(12) 0.0059(10) 0.0087(11) 0.0036(8) -0.0023(9) -0.0012(9) C11 0.0063(12) 0.0099(11) 0.0070(10) 0.0019(9) -0.0028(10) -0.0060(10) H111 0.022(3) 0.036(3) 0.020(2) 0.0089(18) -0.0143(19) -0.013(2) H112 0.016(3) 0.027(2) 0.018(2) 0.000(2) -0.004(2) -0.005(2) H113 0.034(3) 0.023(2) 0.023(2) 0.0094(18) -0.010(2) -0.019(2) C121 0.0038(10) 0.0060(9) 0.0041(9) 0.0013(7) 0.0015(8) 0.0015(8) C122 0.0074(10) 0.0076(10) 0.0041(9) 0.0010(8) 0.0018(8) -0.0006(8) H122 0.023(2) 0.017(2) 0.017(2) 0.0053(17) -0.0057(18) -0.0045(18) C123 0.0096(11) 0.0089(10) 0.0044(11) 0.0013(8) -0.0008(9) -0.0009(8) H123 0.022(2) 0.029(2) 0.014(2) 0.0044(18) 0.0015(19) -0.006(2) C124 0.0082(12) 0.0082(10) 0.0079(10) 0.0000(9) -0.0010(9) -0.0003(10) H124 0.020(3) 0.020(2) 0.023(2) 0.0003(19) 0.000(2) -0.001(2) C125 0.0076(10) 0.0051(10) 0.0083(10) 0.0022(8) -0.0005(8) 0.0017(8) H125 0.029(3) 0.014(2) 0.027(2) 0.0089(18) -0.011(2) -0.0026(19) C126 0.0073(10) 0.0055(9) 0.0071(11) 0.0021(8) 0.0002(8) 0.0012(8) H126 0.022(2) 0.028(2) 0.016(2) 0.0078(17) -0.0062(19) -0.0135(19) C131 0.0036(10) 0.0068(9) 0.0041(9) -0.0004(7) 0.0010(8) -0.0011(8) C132 0.0048(12) 0.0111(9) 0.0056(10) -0.0012(8) -0.0018(9) -0.0021(9) H132 0.010(2) 0.027(2) 0.018(2) -0.0053(19) 0.000(2) -0.002(2) C133 0.0062(11) 0.0123(10) 0.0086(11) -0.0003(8) -0.0025(8) -0.0029(8) H133 0.029(3) 0.034(2) 0.019(2) -0.0036(19) -0.009(2) -0.014(2) C134 0.0058(11) 0.0139(10) 0.0081(10) -0.0005(8) -0.0030(9) -0.0026(8) H134 0.014(2) 0.037(3) 0.026(2) -0.0014(19) -0.011(2) -0.008(2) C135 0.0060(12) 0.0133(10) 0.0091(10) -0.0002(8) -0.0041(10) -0.0047(9) H135 0.013(3) 0.032(2) 0.020(2) -0.006(2) 0.000(2) -0.006(2) C136 0.0068(10) 0.0102(9) 0.0052(10) 0.0002(8) -0.0012(8) -0.0018(8) H136 0.023(2) 0.029(2) 0.013(2) -0.0032(18) -0.0028(18) -0.0078(19) C141 0.0068(10) 0.0072(9) 0.0056(9) 0.0015(7) -0.0019(8) -0.0027(8) C142 0.0059(10) 0.0072(9) 0.0090(9) 0.0023(8) -0.0050(8) -0.0029(8) H142 0.025(2) 0.022(2) 0.026(2) 0.0133(19) -0.021(2) -0.0140(18) C143 0.0095(10) 0.0070(9) 0.0100(9) 0.0044(8) -0.0041(9) -0.0046(8) H143 0.029(3) 0.029(2) 0.031(2) 0.0094(19) -0.018(2) -0.020(2) C144 0.0103(11) 0.0085(10) 0.0098(10) 0.0036(8) -0.0042(8) -0.0064(8) H144 0.033(3) 0.019(2) 0.036(3) 0.0148(19) -0.015(2) -0.017(2) C145 0.0099(10) 0.0061(9) 0.0080(10) 0.0037(8) -0.0032(8) -0.0024(8) H145 0.029(3) 0.023(2) 0.025(2) 0.0145(19) -0.017(2) -0.0100(19) C146 0.0088(10) 0.0088(9) 0.0080(9) 0.0036(7) -0.0051(8) -0.0053(8) H146 0.029(3) 0.031(2) 0.027(2) 0.0093(18) -0.023(2) -0.021(2) C151 0.0063(10) 0.0058(9) 0.0048(9) 0.0019(7) -0.0004(8) -0.0016(8) C152 0.0059(10) 0.0055(9) 0.0059(9) 0.0014(7) -0.0007(8) -0.0026(8) C153 0.0062(10) 0.0069(9) 0.0094(10) 0.0013(7) -0.0019(8) -0.0017(9) H153 0.018(2) 0.021(2) 0.030(2) 0.0053(18) -0.0088(19) -0.011(2) C154 0.0085(12) 0.0078(10) 0.0102(10) 0.0020(8) -0.0029(8) -0.0019(9) H154 0.019(3) 0.024(2) 0.032(2) 0.0059(18) -0.013(2) -0.008(2) C155 0.0057(10) 0.0080(11) 0.0083(9) 0.0027(7) -0.0023(8) -0.0025(8) H155 0.019(2) 0.015(2) 0.033(2) 0.0078(17) -0.0156(19) -0.0077(18) C156 0.0058(10) 0.0050(9) 0.0056(9) 0.0007(7) 0.0000(8) -0.0021(8) C161 0.0066(10) 0.0069(9) 0.0051(9) 0.0022(7) -0.0015(8) -0.0030(8) C162 0.0056(12) 0.0070(9) 0.0091(10) 0.0023(8) -0.0012(9) -0.0026(8) H162 0.015(3) 0.022(2) 0.026(2) -0.0037(18) 0.000(2) -0.0060(19) C163 0.0115(11) 0.0076(11) 0.0103(10) 0.0005(8) -0.0024(9) -0.0056(9) H163 0.023(2) 0.015(2) 0.031(2) -0.006(2) -0.003(2) -0.006(2) C164 0.0084(11) 0.0094(10) 0.0127(10) 0.0009(8) -0.0019(8) -0.0050(9) H164 0.026(3) 0.022(2) 0.039(3) -0.0002(19) -0.007(2) -0.016(2) C165 0.0078(12) 0.0073(9) 0.0109(10) 0.0013(8) -0.0005(9) -0.0045(9) H165 0.012(3) 0.024(2) 0.033(3) -0.0014(19) 0.000(2) -0.0084(19) C166 0.0066(10) 0.0047(10) 0.0074(9) 0.0008(8) 0.0003(8) 0.0000(9) H166 0.022(2) 0.010(2) 0.023(2) -0.0024(18) 0.0023(19) 0.0008(19) C171 0.0059(10) 0.0055(9) 0.0069(9) 0.0013(7) -0.0012(8) -0.0037(8) C172 0.0092(11) 0.0066(9) 0.0083(10) 0.0015(8) -0.0021(9) -0.0042(8) H172 0.023(2) 0.023(2) 0.020(2) 0.0041(18) 0.0022(19) -0.015(2) C173 0.0082(12) 0.0051(9) 0.0099(10) 0.0010(8) -0.0017(9) -0.0022(9) H173 0.016(3) 0.018(2) 0.026(2) -0.0005(19) 0.001(2) -0.004(2) C174 0.0108(11) 0.0096(11) 0.0098(10) 0.0027(8) -0.0035(8) -0.0051(8) H174 0.031(3) 0.017(2) 0.030(2) 0.0086(18) -0.011(2) -0.0115(19) C175 0.0111(11) 0.0086(10) 0.0096(10) 0.0025(8) -0.0028(9) -0.0048(9) H175 0.029(3) 0.027(2) 0.024(2) 0.0080(19) -0.004(2) -0.018(2) C176 0.0057(12) 0.0090(10) 0.0082(10) 0.0001(9) -0.0015(9) -0.0040(10) H176 0.016(3) 0.019(2) 0.021(2) 0.0008(19) 0.006(2) -0.004(2) P21 0.0052(12) 0.0064(11) 0.0030(11) 0.0017(9) -0.0005(10) -0.0016(10) O21 0.0046(11) 0.0032(10) 0.0106(11) 0.0008(8) -0.0016(9) 0.0000(9) C21 0.0072(11) 0.0075(10) 0.0045(9) 0.0011(8) -0.0025(8) -0.0026(10) H211 0.028(2) 0.021(2) 0.016(2) 0.0062(18) -0.0038(18) -0.0152(19) H212 0.020(2) 0.017(2) 0.020(2) -0.0002(17) -0.0064(18) 0.002(2) H213 0.020(2) 0.034(2) 0.026(2) 0.0021(19) -0.013(2) -0.018(2) C221 0.0060(10) 0.0052(9) 0.0052(9) 0.0023(7) -0.0016(8) -0.0022(8) C222 0.0048(10) 0.0071(9) 0.0066(9) 0.0014(8) -0.0011(8) -0.0026(8) H222 0.019(2) 0.020(2) 0.020(2) 0.0075(19) -0.0033(17) -0.0065(18) C223 0.0062(12) 0.0057(9) 0.0062(10) 0.0021(7) -0.0002(10) -0.0001(8) H223 0.014(2) 0.024(2) 0.021(2) 0.0053(18) 0.003(2) -0.0040(18) C224 0.0068(11) 0.0068(10) 0.0066(9) 0.0026(7) -0.0016(8) -0.0017(9) H224 0.016(2) 0.018(2) 0.026(2) 0.0073(18) -0.0036(18) -0.001(2) C225 0.0061(10) 0.0063(9) 0.0075(9) 0.0034(8) -0.0002(8) -0.0016(8) H225 0.023(2) 0.019(2) 0.024(2) 0.0117(19) -0.0058(19) -0.0099(19) C226 0.0049(11) 0.0055(9) 0.0066(10) 0.0031(7) 0.0006(9) -0.0009(8) H226 0.017(2) 0.021(2) 0.023(2) 0.0077(18) 0.005(2) -0.0068(18) C231 0.0075(10) 0.0065(9) 0.0038(9) 0.0019(7) -0.0017(8) -0.0022(8) C232 0.0123(11) 0.0079(9) 0.0061(9) 0.0029(8) -0.0043(8) -0.0048(8) H232 0.037(3) 0.031(2) 0.021(2) 0.0054(19) -0.015(2) -0.027(2) C233 0.0124(11) 0.0098(10) 0.0059(11) 0.0039(8) -0.0026(8) -0.0052(8) H233 0.038(3) 0.028(2) 0.012(2) 0.0069(17) -0.0092(19) -0.019(2) C234 0.0127(11) 0.0081(9) 0.0082(10) 0.0029(8) -0.0012(8) -0.0056(9) H234 0.037(3) 0.024(2) 0.025(2) 0.013(2) -0.008(2) -0.021(2) C235 0.0172(12) 0.0101(10) 0.0089(10) 0.0037(8) -0.0035(9) -0.0094(9) H235 0.043(3) 0.034(3) 0.028(2) 0.006(2) -0.015(2) -0.033(2) C236 0.0128(11) 0.0086(9) 0.0082(11) 0.0017(8) -0.0039(8) -0.0073(8) H236 0.040(3) 0.032(2) 0.019(2) 0.0088(18) -0.014(2) -0.028(2) C241 0.0056(10) 0.0055(9) 0.0054(9) 0.0007(7) -0.0011(8) -0.0011(8) C242 0.0085(13) 0.0072(9) 0.0082(9) -0.0004(8) -0.0031(8) -0.0031(10) H242 0.016(3) 0.020(2) 0.025(2) -0.0059(18) -0.0052(19) 0.001(2) C243 0.0108(11) 0.0103(10) 0.0113(10) 0.0007(9) -0.0064(9) -0.0062(9) H243 0.027(3) 0.027(2) 0.026(2) -0.006(2) -0.011(2) -0.012(2) C244 0.0119(11) 0.0128(10) 0.0113(10) 0.0043(8) -0.0054(9) -0.0070(9) H244 0.029(3) 0.034(3) 0.033(3) 0.001(2) -0.017(2) -0.016(2) C245 0.0055(12) 0.0110(10) 0.0110(10) 0.0018(8) -0.0037(9) -0.0026(10) H245 0.015(3) 0.026(2) 0.030(2) -0.0020(19) -0.0069(19) -0.003(2) C246 0.0062(10) 0.0075(10) 0.0083(10) 0.0020(9) -0.0039(8) -0.0031(8) H246 0.019(2) 0.020(2) 0.019(2) -0.005(2) -0.0051(18) -0.0032(18) C251 0.0061(10) 0.0051(9) 0.0048(9) 0.0014(7) -0.0006(8) -0.0018(8) C252 0.0065(10) 0.0061(9) 0.0060(9) 0.0019(7) -0.0010(8) -0.0016(8) C253 0.0082(11) 0.0060(9) 0.0083(10) 0.0024(7) -0.0020(8) -0.0015(9) H253 0.015(2) 0.019(2) 0.032(2) 0.0071(18) -0.0127(19) -0.0062(18) C254 0.0092(11) 0.0052(11) 0.0094(10) 0.0021(7) -0.0030(8) -0.0019(9) H254 0.027(3) 0.012(2) 0.031(2) 0.0041(18) -0.009(2) 0.0000(19) C255 0.0086(10) 0.0056(9) 0.0083(9) 0.0017(7) -0.0025(8) -0.0018(8) H255 0.022(2) 0.020(2) 0.030(2) 0.0027(18) -0.011(2) -0.0099(19) C256 0.0072(10) 0.0050(9) 0.0060(9) 0.0015(7) -0.0021(8) -0.0024(8) C261 0.0062(10) 0.0057(9) 0.0058(9) 0.0001(7) -0.0012(8) 0.0001(8) C262 0.0095(11) 0.0072(9) 0.0079(10) 0.0025(8) 0.0001(8) -0.0031(8) H262 0.026(2) 0.024(2) 0.027(2) 0.017(2) -0.015(2) -0.0155(19) C263 0.0076(11) 0.0105(9) 0.0094(10) 0.0011(8) -0.0009(8) -0.0038(9) H263 0.019(2) 0.029(2) 0.034(2) 0.010(2) -0.011(2) -0.018(2) C264 0.0083(12) 0.0104(10) 0.0098(10) 0.0005(8) -0.0041(8) -0.0034(9) H264 0.018(3) 0.032(2) 0.031(2) 0.0077(19) -0.016(2) -0.010(2) C265 0.0076(10) 0.0111(10) 0.0102(10) 0.0030(9) -0.0048(8) -0.0048(8) H265 0.025(2) 0.026(2) 0.031(2) 0.015(2) -0.014(2) -0.017(2) C266 0.0080(10) 0.0085(9) 0.0070(9) 0.0030(8) -0.0020(8) -0.0041(8) H266 0.019(2) 0.027(2) 0.027(2) 0.0121(19) -0.0087(19) -0.017(2) C271 0.0048(10) 0.0083(9) 0.0068(9) 0.0027(7) -0.0036(8) -0.0042(8) C272 0.0067(10) 0.0086(9) 0.0088(10) 0.0051(8) -0.0045(9) -0.0039(8) H272 0.027(2) 0.029(2) 0.030(2) 0.0164(19) -0.024(2) -0.018(2) C273 0.0091(11) 0.0093(10) 0.0097(10) 0.0029(8) -0.0038(8) -0.0045(8) H273 0.033(3) 0.022(2) 0.036(3) 0.017(2) -0.023(2) -0.020(2) C274 0.0122(11) 0.0126(10) 0.0089(10) 0.0023(8) -0.0038(9) -0.0058(9) H274 0.028(3) 0.033(2) 0.030(2) 0.010(2) -0.015(2) -0.022(2) C275 0.0107(11) 0.0135(10) 0.0107(10) 0.0057(8) -0.0068(9) -0.0068(8) H275 0.035(3) 0.041(3) 0.030(2) 0.018(2) -0.026(2) -0.021(2) C276 0.0079(10) 0.0101(10) 0.0088(9) 0.0041(8) -0.0058(8) -0.0046(8) H276 0.033(3) 0.024(2) 0.031(2) 0.017(2) -0.019(2) -0.018(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 P11 C131 1.781(3) . ? P11 C11 1.784(3) . ? P11 C121 1.791(3) . ? P11 C141 1.796(3) . ? O11 C151 1.292(3) . ? C11 H111 1.100(5) . ? C11 H112 1.098(5) . ? C11 H113 1.086(5) . ? C121 C122 1.400(3) . ? C121 C126 1.404(3) . ? C122 C123 1.399(3) . ? C122 H122 1.086(4) . ? C123 C124 1.392(3) . ? C123 H123 1.089(5) . ? C124 C125 1.396(3) . ? C124 H124 1.085(5) . ? C125 C126 1.396(3) . ? C125 H125 1.085(4) . ? C126 H126 1.090(5) . ? C131 C132 1.401(3) . ? C131 C136 1.411(3) . ? C132 C133 1.400(3) . ? C132 H132 1.088(5) . ? C133 C134 1.397(3) . ? C133 H133 1.087(5) . ? C134 C135 1.398(3) . ? C134 H134 1.090(5) . ? C135 C136 1.390(3) . ? C135 H135 1.090(5) . ? C136 H136 1.088(5) . ? C141 C146 1.396(3) . ? C141 C142 1.401(3) . ? C142 C143 1.396(3) . ? C142 H142 1.090(4) . ? C143 C144 1.398(3) . ? C143 H143 1.070(5) . ? C144 C145 1.389(3) . ? C144 H144 1.083(5) . ? C145 C146 1.394(3) . ? C145 H145 1.083(4) . ? C146 H146 1.100(4) . ? C151 C156 1.440(3) . ? C151 C152 1.445(3) . ? C152 C153 1.400(3) . ? C152 C171 1.482(3) . ? C153 C154 1.399(3) . ? C153 H153 1.077(5) . ? C154 C155 1.397(3) . ? C154 H154 1.084(5) . ? C155 C156 1.401(3) . ? C155 H155 1.090(4) . ? C156 C161 1.486(3) . ? C161 C166 1.398(3) . ? C161 C162 1.401(3) . ? C162 C163 1.406(3) . ? C162 H162 1.087(5) . ? C163 C164 1.400(3) . ? C163 H163 1.091(5) . ? C164 C165 1.391(3) . ? C164 H164 1.085(5) . ? C165 C166 1.407(3) . ? C165 H165 1.084(5) . ? C166 H166 1.081(5) . ? C171 C176 1.400(3) . ? C171 C172 1.410(3) . ? C172 C173 1.392(3) . ? C172 H172 1.077(5) . ? C173 C174 1.402(3) . ? C173 H173 1.095(5) . ? C174 C175 1.399(3) . ? C174 H174 1.084(5) . ? C175 C176 1.395(3) . ? C175 H175 1.089(5) . ? C176 H176 1.090(5) . ? P21 C21 1.771(3) . ? P21 C221 1.790(3) . ? P21 C231 1.792(3) . ? P21 C241 1.796(3) . ? O21 C251 1.287(3) . ? C21 H211 1.102(4) . ? C21 H212 1.105(5) . ? C21 H213 1.090(5) . ? C221 C222 1.402(3) . ? C221 C226 1.406(3) . ? C222 C223 1.395(3) . ? C222 H222 1.081(4) . ? C223 C224 1.399(3) . ? C223 H223 1.082(5) . ? C224 C225 1.397(3) . ? C224 H224 1.083(5) . ? C225 C226 1.395(3) . ? C225 H225 1.085(4) . ? C226 H226 1.083(5) . ? C231 C232 1.398(3) . ? C231 C236 1.410(3) . ? C232 C233 1.391(3) . ? C232 H232 1.081(4) . ? C233 C234 1.403(3) . ? C233 H233 1.087(4) . ? C234 C235 1.389(3) . ? C234 H234 1.087(4) . ? C235 C236 1.393(3) . ? C235 H235 1.095(4) . ? C236 H236 1.084(5) . ? C241 C242 1.397(3) . ? C241 C246 1.406(3) . ? C242 C243 1.400(3) . ? C242 H242 1.092(5) . ? C243 C244 1.401(3) . ? C243 H243 1.080(5) . ? C244 C245 1.390(3) . ? C244 H244 1.076(5) . ? C245 C246 1.400(3) . ? C245 H245 1.089(5) . ? C246 H246 1.095(5) . ? C251 C256 1.430(3) . ? C251 C252 1.452(3) . ? C252 C253 1.396(3) . ? C252 C271 1.488(3) . ? C253 C254 1.408(3) . ? C253 H253 1.094(5) . ? C254 C255 1.396(3) . ? C254 H254 1.078(5) . ? C255 C256 1.404(3) . ? C255 H255 1.060(5) . ? C256 C261 1.491(3) . ? C261 C262 1.401(3) . ? C261 C266 1.405(3) . ? C262 C263 1.402(3) . ? C262 H262 1.087(4) . ? C263 C264 1.399(3) . ? C263 H263 1.092(5) . ? C264 C265 1.401(3) . ? C264 H264 1.083(5) . ? C265 C266 1.396(3) . ? C265 H265 1.079(5) . ? C266 H266 1.092(5) . ? C271 C272 1.405(3) . ? C271 C276 1.407(3) . ? C272 C273 1.404(3) . ? C272 H272 1.077(4) . ? C273 C274 1.397(3) . ? C273 H273 1.082(4) . ? C274 C275 1.399(3) . ? C274 H274 1.069(5) . ? C275 C276 1.386(3) . ? C275 H275 1.093(4) . ? C276 H276 1.087(4) . ? 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 C131 P11 C11 110.53(16) . . ? C131 P11 C121 112.56(16) . . ? C11 P11 C121 108.47(15) . . ? C131 P11 C141 105.93(15) . . ? C11 P11 C141 110.78(16) . . ? C121 P11 C141 108.55(16) . . ? P11 C11 H111 109.2(3) . . ? P11 C11 H112 111.6(3) . . ? H111 C11 H112 110.9(4) . . ? P11 C11 H113 108.9(3) . . ? H111 C11 H113 108.5(4) . . ? H112 C11 H113 107.7(4) . . ? C122 C121 C126 119.87(18) . . ? C122 C121 P11 119.13(16) . . ? C126 C121 P11 120.93(17) . . ? C123 C122 C121 119.78(18) . . ? C123 C122 H122 119.6(3) . . ? C121 C122 H122 120.6(3) . . ? C124 C123 C122 120.17(19) . . ? C124 C123 H123 120.1(3) . . ? C122 C123 H123 119.7(3) . . ? C123 C124 C125 120.3(2) . . ? C123 C124 H124 119.7(3) . . ? C125 C124 H124 120.0(3) . . ? C126 C125 C124 119.93(18) . . ? C126 C125 H125 119.6(3) . . ? C124 C125 H125 120.4(3) . . ? C125 C126 C121 119.97(18) . . ? C125 C126 H126 119.5(3) . . ? C121 C126 H126 120.5(3) . . ? C132 C131 C136 119.89(18) . . ? C132 C131 P11 122.55(17) . . ? C136 C131 P11 117.26(16) . . ? C133 C132 C131 119.51(19) . . ? C133 C132 H132 119.4(3) . . ? C131 C132 H132 121.1(3) . . ? C134 C133 C132 120.30(19) . . ? C134 C133 H133 120.0(3) . . ? C132 C133 H133 119.7(3) . . ? C133 C134 C135 120.28(19) . . ? C133 C134 H134 119.4(3) . . ? C135 C134 H134 120.4(3) . . ? C136 C135 C134 119.79(19) . . ? C136 C135 H135 119.2(3) . . ? C134 C135 H135 121.0(3) . . ? C135 C136 C131 120.22(18) . . ? C135 C136 H136 119.6(3) . . ? C131 C136 H136 120.2(3) . . ? C146 C141 C142 120.73(18) . . ? C146 C141 P11 120.34(17) . . ? C142 C141 P11 118.84(16) . . ? C143 C142 C141 118.94(18) . . ? C143 C142 H142 119.9(3) . . ? C141 C142 H142 121.1(3) . . ? C142 C143 C144 120.20(19) . . ? C142 C143 H143 119.1(3) . . ? C144 C143 H143 120.7(3) . . ? C145 C144 C143 120.54(18) . . ? C145 C144 H144 119.7(3) . . ? C143 C144 H144 119.7(3) . . ? C144 C145 C146 119.67(18) . . ? C144 C145 H145 119.9(3) . . ? C146 C145 H145 120.4(3) . . ? C145 C146 C141 119.90(18) . . ? C145 C146 H146 119.2(3) . . ? C141 C146 H146 120.9(3) . . ? O11 C151 C156 121.73(19) . . ? O11 C151 C152 121.37(18) . . ? C156 C151 C152 116.83(18) . . ? C153 C152 C151 120.81(17) . . ? C153 C152 C171 119.22(18) . . ? C151 C152 C171 119.92(17) . . ? C154 C153 C152 121.36(19) . . ? C154 C153 H153 119.6(3) . . ? C152 C153 H153 119.0(3) . . ? C155 C154 C153 118.62(19) . . ? C155 C154 H154 121.4(3) . . ? C153 C154 H154 119.9(3) . . ? C154 C155 C156 122.17(18) . . ? C154 C155 H155 118.6(3) . . ? C156 C155 H155 119.2(3) . . ? C155 C156 C151 120.14(18) . . ? C155 C156 C161 119.27(17) . . ? C151 C156 C161 120.52(17) . . ? C166 C161 C162 118.58(18) . . ? C166 C161 C156 122.13(18) . . ? C162 C161 C156 119.23(18) . . ? C161 C162 C163 120.86(19) . . ? C161 C162 H162 119.7(3) . . ? C163 C162 H162 119.4(3) . . ? C164 C163 C162 120.06(19) . . ? C164 C163 H163 120.3(3) . . ? C162 C163 H163 119.6(3) . . ? C165 C164 C163 119.33(19) . . ? C165 C164 H164 120.5(3) . . ? C163 C164 H164 120.2(3) . . ? C164 C165 C166 120.5(2) . . ? C164 C165 H165 120.5(3) . . ? C166 C165 H165 119.1(3) . . ? C161 C166 C165 120.70(18) . . ? C161 C166 H166 120.5(3) . . ? C165 C166 H166 118.8(3) . . ? C176 C171 C172 117.69(17) . . ? C176 C171 C152 120.01(18) . . ? C172 C171 C152 122.26(18) . . ? C173 C172 C171 120.94(19) . . ? C173 C172 H172 120.2(3) . . ? C171 C172 H172 118.9(3) . . ? C172 C173 C174 120.7(2) . . ? C172 C173 H173 119.5(3) . . ? C174 C173 H173 119.8(3) . . ? C175 C174 C173 118.89(18) . . ? C175 C174 H174 120.4(3) . . ? C173 C174 H174 120.7(3) . . ? C176 C175 C174 120.1(2) . . ? C176 C175 H175 120.3(3) . . ? C174 C175 H175 119.5(3) . . ? C175 C176 C171 121.6(2) . . ? C175 C176 H176 120.2(3) . . ? C171 C176 H176 118.2(3) . . ? C21 P21 C221 109.68(15) . . ? C21 P21 C231 109.77(16) . . ? C221 P21 C231 109.99(16) . . ? C21 P21 C241 110.95(16) . . ? C221 P21 C241 108.77(15) . . ? C231 P21 C241 107.64(15) . . ? P21 C21 H211 111.0(3) . . ? P21 C21 H212 109.8(3) . . ? H211 C21 H212 110.4(4) . . ? P21 C21 H213 108.1(3) . . ? H211 C21 H213 108.2(4) . . ? H212 C21 H213 109.3(4) . . ? C222 C221 C226 120.57(17) . . ? C222 C221 P21 121.96(16) . . ? C226 C221 P21 117.47(17) . . ? C223 C222 C221 119.49(18) . . ? C223 C222 H222 119.4(3) . . ? C221 C222 H222 121.1(3) . . ? C222 C223 C224 120.03(19) . . ? C222 C223 H223 119.8(3) . . ? C224 C223 H223 120.2(3) . . ? C225 C224 C223 120.43(18) . . ? C225 C224 H224 120.8(3) . . ? C223 C224 H224 118.7(3) . . ? C226 C225 C224 120.03(18) . . ? C226 C225 H225 118.5(3) . . ? C224 C225 H225 121.4(3) . . ? C225 C226 C221 119.45(19) . . ? C225 C226 H226 119.4(3) . . ? C221 C226 H226 121.1(3) . . ? C232 C231 C236 119.85(18) . . ? C232 C231 P21 119.55(17) . . ? C236 C231 P21 120.59(16) . . ? C233 C232 C231 120.14(19) . . ? C233 C232 H232 119.7(3) . . ? C231 C232 H232 120.2(3) . . ? C232 C233 C234 120.13(18) . . ? C232 C233 H233 119.9(3) . . ? C234 C233 H233 120.0(3) . . ? C235 C234 C233 119.59(18) . . ? C235 C234 H234 121.9(3) . . ? C233 C234 H234 118.5(3) . . ? C234 C235 C236 120.98(19) . . ? C234 C235 H235 120.2(3) . . ? C236 C235 H235 118.8(3) . . ? C235 C236 C231 119.29(18) . . ? C235 C236 H236 119.6(3) . . ? C231 C236 H236 121.0(3) . . ? C242 C241 C246 120.95(19) . . ? C242 C241 P21 119.35(17) . . ? C246 C241 P21 119.46(17) . . ? C241 C242 C243 119.49(19) . . ? C241 C242 H242 120.7(3) . . ? C243 C242 H242 119.9(3) . . ? C242 C243 C244 119.75(19) . . ? C242 C243 H243 119.0(3) . . ? C244 C243 H243 121.3(3) . . ? C245 C244 C243 120.5(2) . . ? C245 C244 H244 119.9(3) . . ? C243 C244 H244 119.6(3) . . ? C244 C245 C246 120.5(2) . . ? C244 C245 H245 120.8(3) . . ? C246 C245 H245 118.7(3) . . ? C245 C246 C241 118.88(19) . . ? C245 C246 H246 119.9(3) . . ? C241 C246 H246 121.2(3) . . ? O21 C251 C256 122.1(2) . . ? O21 C251 C252 121.26(19) . . ? C256 C251 C252 116.65(17) . . ? C253 C252 C251 120.18(18) . . ? C253 C252 C271 118.87(18) . . ? C251 C252 C271 120.95(17) . . ? C252 C253 C254 121.88(19) . . ? C252 C253 H253 119.4(3) . . ? C254 C253 H253 118.7(3) . . ? C255 C254 C253 118.71(18) . . ? C255 C254 H254 121.5(4) . . ? C253 C254 H254 119.8(3) . . ? C254 C255 C256 121.01(19) . . ? C254 C255 H255 119.7(3) . . ? C256 C255 H255 119.2(3) . . ? C255 C256 C251 121.48(18) . . ? C255 C256 C261 117.78(18) . . ? C251 C256 C261 120.73(17) . . ? C262 C261 C266 117.69(19) . . ? C262 C261 C256 120.43(17) . . ? C266 C261 C256 121.83(19) . . ? C261 C262 C263 121.37(18) . . ? C261 C262 H262 120.0(3) . . ? C263 C262 H262 118.6(3) . . ? C264 C263 C262 120.30(19) . . ? C264 C263 H263 119.2(3) . . ? C262 C263 H263 120.5(3) . . ? C263 C264 C265 118.8(2) . . ? C263 C264 H264 120.7(3) . . ? C265 C264 H264 120.4(3) . . ? C266 C265 C264 120.51(18) . . ? C266 C265 H265 119.5(3) . . ? C264 C265 H265 120.0(3) . . ? C265 C266 C261 121.31(19) . . ? C265 C266 H266 119.4(3) . . ? C261 C266 H266 119.3(3) . . ? C272 C271 C276 117.39(18) . . ? C272 C271 C252 122.08(17) . . ? C276 C271 C252 120.52(17) . . ? C273 C272 C271 120.78(18) . . ? C273 C272 H272 120.1(3) . . ? C271 C272 H272 119.1(3) . . ? C274 C273 C272 120.90(18) . . ? C274 C273 H273 120.0(3) . . ? C272 C273 H273 119.1(3) . . ? C273 C274 C275 118.5(2) . . ? C273 C274 H274 120.8(3) . . ? C275 C274 H274 120.7(3) . . ? C276 C275 C274 120.63(19) . . ? C276 C275 H275 119.5(3) . . ? C274 C275 H275 119.9(3) . . ? C275 C276 C271 121.82(18) . . ? C275 C276 H276 119.8(3) . . ? C271 C276 H276 118.4(3) . . ? #===END data_1b _chemical_formula_sum 'C35 H43 O P' _chemical_formula_weight 510.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0000 0.0000 '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' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pbca' 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' '-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 18.570(1) _cell_length_b 17.220(1) _cell_length_c 19.030(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6085.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 20(2) _cell_measurement_reflns_used 3298 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 50.2 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 3.5 _exptl_crystal_size_mid 3.5 _exptl_crystal_size_min 2.4 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.113 _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.3577 _exptl_absorpt_correction_T_max 0.5501 _diffrn_ambient_temperature 20(2) _diffrn_radiation_wavelength 1.3137 _diffrn_radiation_type neutron _diffrn_source 'nuclear reactor' _diffrn_radiation_monochromator 'Ge 115' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_details ; D19 - ILL ; _diffrn_measurement_method 'omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 400 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10445 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 50.63 _reflns_number_total 4995 _reflns_number_observed 4467 _reflns_observed_criterion >2sigma(I) _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+19.6161P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00027(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4995 _refine_ls_number_parameters 722 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_obs 0.0357 _refine_ls_wR_factor_all 0.0738 _refine_ls_wR_factor_obs 0.0713 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.439 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.106 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 -0.44206(8) 0.46805(8) 0.35257(8) 0.0055(3) Uani 1 1 d . . . C1 C -0.40628(7) 0.44739(7) 0.26639(7) 0.0084(3) Uani 1 1 d . . . H101 H -0.35352(15) 0.42014(17) 0.27629(15) 0.0248(6) Uani 1 1 d . . . H102 H -0.44201(17) 0.40346(16) 0.24421(16) 0.0247(6) Uani 1 1 d . . . C2 C -0.39872(8) 0.51705(8) 0.21722(7) 0.0140(3) Uani 1 1 d . . . H201 H -0.3804(2) 0.49704(19) 0.16595(16) 0.0360(8) Uani 1 1 d . . . H202 H -0.3589(2) 0.55793(18) 0.23644(18) 0.0368(8) Uani 1 1 d . . . H203 H -0.4496(2) 0.54794(19) 0.21006(19) 0.0377(8) Uani 1 1 d . . . C11 C -0.38772(7) 0.53820(7) 0.39771(7) 0.0063(2) Uani 1 1 d . . . C12 C -0.38443(7) 0.61494(7) 0.37242(7) 0.0080(3) Uani 1 1 d . . . H12 H -0.41334(16) 0.63217(15) 0.32553(16) 0.0245(6) Uani 1 1 d . . . C13 C -0.34466(7) 0.67049(7) 0.40886(7) 0.0086(3) Uani 1 1 d . . . H13 H -0.34239(16) 0.72971(15) 0.38897(16) 0.0241(6) Uani 1 1 d . . . C14 C -0.30923(7) 0.65033(7) 0.47103(7) 0.0082(3) Uani 1 1 d . . . H14 H -0.27959(16) 0.69380(16) 0.50053(16) 0.0249(6) Uani 1 1 d . . . C15 C -0.31251(7) 0.57393(7) 0.49595(7) 0.0082(3) Uani 1 1 d . . . H15 H -0.28474(16) 0.55795(16) 0.54400(16) 0.0247(6) Uani 1 1 d . . . C16 C -0.35126(7) 0.51791(7) 0.45921(7) 0.0074(3) Uani 1 1 d . . . H16 H -0.35304(16) 0.45890(15) 0.47835(15) 0.0212(6) Uani 1 1 d . . . C21 C -0.44272(7) 0.37732(7) 0.39917(6) 0.0063(2) Uani 1 1 d . . . C22 C -0.38082(7) 0.33072(7) 0.39686(7) 0.0076(3) Uani 1 1 d . . . H22 H -0.33253(15) 0.34876(15) 0.36846(15) 0.0210(6) Uani 1 1 d . . . C23 C -0.38113(7) 0.25898(7) 0.43152(7) 0.0094(3) Uani 1 1 d . . . H23 H -0.33350(16) 0.22249(16) 0.42883(17) 0.0262(6) Uani 1 1 d . . . C24 C -0.44213(7) 0.23491(7) 0.46824(7) 0.0100(3) Uani 1 1 d . . . H24 H -0.44213(16) 0.17898(16) 0.49478(17) 0.0264(6) Uani 1 1 d . . . C25 C -0.50348(7) 0.28138(7) 0.47053(7) 0.0093(3) Uani 1 1 d . . . H25 H -0.55102(15) 0.26209(16) 0.49925(17) 0.0263(6) Uani 1 1 d . . . C26 C -0.50435(7) 0.35275(7) 0.43575(7) 0.0081(3) Uani 1 1 d . . . H26 H -0.55252(15) 0.38841(16) 0.43683(16) 0.0235(6) Uani 1 1 d . . . C31 C -0.53176(7) 0.50587(7) 0.34790(7) 0.0066(2) Uani 1 1 d . . . C32 C -0.58079(7) 0.47273(7) 0.30061(7) 0.0082(3) Uani 1 1 d . . . H32 H -0.56484(15) 0.42653(16) 0.26483(16) 0.0241(6) Uani 1 1 d . . . C33 C -0.65208(7) 0.49838(7) 0.30009(7) 0.0085(3) Uani 1 1 d . . . H33 H -0.69023(15) 0.47277(16) 0.26341(15) 0.0232(6) Uani 1 1 d . . . C34 C -0.67417(7) 0.55644(7) 0.34657(7) 0.0082(3) Uani 1 1 d . . . H34 H -0.72973(14) 0.57623(16) 0.34599(16) 0.0230(6) Uani 1 1 d . . . C35 C -0.62493(7) 0.59022(7) 0.39294(7) 0.0082(3) Uani 1 1 d . . . H35 H -0.64176(16) 0.63663(16) 0.42775(16) 0.0238(6) Uani 1 1 d . . . C36 C -0.55367(7) 0.56479(7) 0.39402(7) 0.0077(3) Uani 1 1 d . . . H36 H -0.51561(15) 0.59096(16) 0.43024(15) 0.0232(6) Uani 1 1 d . . . O1 O -0.24417(8) 0.38047(8) 0.31590(7) 0.0068(3) Uani 1 1 d . . . C41 C -0.17962(7) 0.35270(7) 0.30964(6) 0.0056(2) Uani 1 1 d . . . C42 C -0.12266(7) 0.37473(7) 0.35729(7) 0.0063(2) Uani 1 1 d . . . C43 C -0.05379(7) 0.34283(7) 0.34941(7) 0.0072(3) Uani 1 1 d . . . H43 H -0.01106(15) 0.35869(16) 0.38593(15) 0.0223(6) Uani 1 1 d . . . C44 C -0.03639(7) 0.29046(7) 0.29581(7) 0.0074(2) Uani 1 1 d . . . C45 C -0.09135(7) 0.27014(7) 0.24889(7) 0.0074(3) Uani 1 1 d . . . H45 H -0.07735(15) 0.22969(15) 0.20679(15) 0.0211(6) Uani 1 1 d . . . C46 C -0.16116(7) 0.29848(7) 0.25413(6) 0.0060(2) Uani 1 1 d . . . C47 C 0.03753(7) 0.25464(7) 0.28959(7) 0.0103(3) Uani 1 1 d . . . H471 H 0.05963(18) 0.2604(2) 0.23712(18) 0.0367(8) Uani 1 1 d . . . H472 H 0.03745(18) 0.19301(17) 0.3010(2) 0.0386(8) Uani 1 1 d . . . H473 H 0.07571(17) 0.2815(2) 0.3253(2) 0.0381(8) Uani 1 1 d . . . C48 C -0.13838(7) 0.43169(7) 0.41768(7) 0.0073(3) Uani 1 1 d . . . C49 C -0.07133(7) 0.45009(8) 0.46173(7) 0.0124(3) Uani 1 1 d . . . H491 H -0.02876(16) 0.47712(19) 0.43003(18) 0.0303(7) Uani 1 1 d . . . H492 H -0.04936(17) 0.39878(18) 0.48772(17) 0.0298(7) Uani 1 1 d . . . H493 H -0.08576(17) 0.49135(18) 0.50310(17) 0.0305(7) Uani 1 1 d . . . C50 C -0.19413(7) 0.39509(7) 0.46793(7) 0.0102(3) Uani 1 1 d . . . H501 H -0.17245(17) 0.34224(17) 0.49182(17) 0.0291(7) Uani 1 1 d . . . H502 H -0.24348(16) 0.38070(19) 0.43979(16) 0.0279(6) Uani 1 1 d . . . H503 H -0.20697(17) 0.43492(17) 0.51094(16) 0.0281(7) Uani 1 1 d . . . C51 C -0.16633(7) 0.50967(7) 0.38878(7) 0.0093(3) Uani 1 1 d . . . H511 H -0.12621(17) 0.53565(17) 0.35362(17) 0.0294(7) Uani 1 1 d . . . H512 H -0.17636(18) 0.55040(16) 0.43183(16) 0.0281(7) Uani 1 1 d . . . H513 H -0.21642(16) 0.50190(16) 0.35987(17) 0.0272(6) Uani 1 1 d . . . C52 C -0.21998(6) 0.26912(7) 0.20395(6) 0.0057(2) Uani 1 1 d . . . C53 C -0.27532(7) 0.22223(7) 0.24690(7) 0.0086(3) Uani 1 1 d . . . H531 H -0.31940(16) 0.20176(17) 0.21354(16) 0.0252(6) Uani 1 1 d . . . H532 H -0.29773(16) 0.25819(16) 0.28850(16) 0.0259(6) Uani 1 1 d . . . H533 H -0.24995(16) 0.17140(17) 0.27092(16) 0.0275(6) Uani 1 1 d . . . C54 C -0.18977(7) 0.21625(7) 0.14592(7) 0.0086(3) Uani 1 1 d . . . H541 H -0.23376(16) 0.19915(17) 0.11061(16) 0.0258(6) Uani 1 1 d . . . H542 H -0.16569(17) 0.16296(16) 0.16649(16) 0.0264(6) Uani 1 1 d . . . H543 H -0.14891(16) 0.24587(17) 0.11391(15) 0.0249(6) Uani 1 1 d . . . C55 C -0.25778(7) 0.33669(7) 0.16579(7) 0.0090(3) Uani 1 1 d . . . H551 H -0.30022(17) 0.31423(17) 0.13101(17) 0.0282(7) Uani 1 1 d . . . H552 H -0.21904(17) 0.36825(17) 0.13332(16) 0.0276(6) Uani 1 1 d . . . H553 H -0.28136(18) 0.37702(16) 0.20284(16) 0.0273(6) Uani 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 P1 0.0055(7) 0.0031(7) 0.0080(8) 0.0002(5) 0.0008(6) 0.0005(6) C1 0.0103(7) 0.0069(6) 0.0081(6) 0.0000(5) 0.0015(5) -0.0003(6) H101 0.0209(16) 0.0301(14) 0.0233(14) 0.0029(11) 0.0032(12) 0.0074(12) H102 0.0307(15) 0.0191(13) 0.0243(14) -0.0032(11) 0.0012(12) -0.0094(12) C2 0.0206(8) 0.0110(6) 0.0104(8) 0.0028(6) 0.0040(6) -0.0008(7) H201 0.058(2) 0.0322(16) 0.0178(17) 0.0008(13) 0.0127(15) 0.0019(15) H202 0.052(2) 0.0246(15) 0.0334(18) 0.0053(13) 0.0016(16) -0.0193(16) H203 0.040(2) 0.0315(16) 0.0418(19) 0.0142(14) 0.0019(15) 0.0173(16) C11 0.0080(6) 0.0034(5) 0.0075(6) 0.0007(4) -0.0010(5) -0.0001(5) C12 0.0102(6) 0.0042(5) 0.0096(7) 0.0003(5) -0.0007(6) -0.0010(5) H12 0.0317(15) 0.0180(12) 0.0239(15) 0.0050(11) -0.0108(14) -0.0039(11) C13 0.0100(6) 0.0039(6) 0.0119(6) 0.0006(5) -0.0005(5) -0.0017(5) H13 0.0318(15) 0.0114(13) 0.0291(15) 0.0045(11) -0.0045(12) -0.0033(11) C14 0.0105(6) 0.0045(6) 0.0096(6) -0.0009(5) -0.0001(5) -0.0023(5) H14 0.0315(15) 0.0163(12) 0.0268(14) -0.0069(12) -0.0060(13) -0.0069(12) C15 0.0101(6) 0.0046(5) 0.0099(7) -0.0009(5) -0.0016(6) 0.0000(5) H15 0.0312(15) 0.0214(13) 0.0214(15) -0.0005(11) -0.0138(13) -0.0018(12) C16 0.0093(6) 0.0055(6) 0.0073(6) 0.0003(5) -0.0016(5) -0.0008(5) H16 0.0288(14) 0.0100(13) 0.0248(14) 0.0050(10) -0.0081(12) -0.0024(10) C21 0.0069(6) 0.0045(5) 0.0075(6) 0.0009(4) 0.0009(5) 0.0004(4) C22 0.0082(6) 0.0039(5) 0.0107(6) 0.0013(5) 0.0009(5) 0.0010(5) H22 0.0145(14) 0.0207(12) 0.0278(15) 0.0042(11) 0.0045(12) 0.0016(10) C23 0.0098(6) 0.0050(6) 0.0134(6) 0.0032(5) 0.0016(5) 0.0010(5) H23 0.0203(15) 0.0203(13) 0.0381(17) 0.0062(12) 0.0049(12) 0.0060(12) C24 0.0100(6) 0.0056(6) 0.0142(6) 0.0034(5) 0.0023(5) 0.0004(5) H24 0.0276(15) 0.0154(13) 0.0363(16) 0.0115(12) 0.0061(13) 0.0021(11) C25 0.0094(6) 0.0046(5) 0.0138(6) 0.0032(5) 0.0031(6) 0.0000(5) H25 0.0198(14) 0.0231(13) 0.0360(16) 0.0091(12) 0.0136(14) -0.0025(11) C26 0.0079(6) 0.0046(5) 0.0118(6) 0.0018(4) 0.0026(5) 0.0004(5) H26 0.0157(13) 0.0200(13) 0.0348(16) 0.0040(11) 0.0067(12) 0.0044(12) C31 0.0068(6) 0.0048(5) 0.0082(6) 0.0002(4) -0.0007(5) -0.0002(4) C32 0.0069(6) 0.0069(6) 0.0108(6) -0.0016(5) -0.0019(5) 0.0008(5) H32 0.0216(13) 0.0213(13) 0.0295(15) -0.0124(12) -0.0040(12) 0.0046(11) C33 0.0072(6) 0.0063(5) 0.0119(6) -0.0015(5) -0.0007(5) 0.0005(5) H33 0.0193(13) 0.0247(13) 0.0257(15) -0.0087(11) -0.0073(13) 0.0001(11) C34 0.0071(7) 0.0062(5) 0.0113(6) 0.0001(5) -0.0008(5) 0.0010(5) H34 0.0147(15) 0.0223(13) 0.0320(15) -0.0037(11) -0.0004(11) 0.0065(11) C35 0.0080(6) 0.0067(6) 0.0099(6) -0.0003(5) -0.0005(5) 0.0014(5) H35 0.0234(14) 0.0207(13) 0.0275(15) -0.0100(12) -0.0006(12) 0.0057(11) C36 0.0081(6) 0.0059(5) 0.0090(6) -0.0014(5) -0.0001(5) 0.0008(5) H36 0.0219(14) 0.0239(13) 0.0238(15) -0.0095(11) -0.0068(13) 0.0007(11) O1 0.0063(7) 0.0058(6) 0.0084(7) -0.0010(5) 0.0018(6) 0.0016(5) C41 0.0045(6) 0.0051(5) 0.0073(6) 0.0000(4) -0.0004(5) 0.0002(4) C42 0.0058(6) 0.0052(5) 0.0077(6) -0.0008(4) -0.0009(5) 0.0002(5) C43 0.0055(6) 0.0073(5) 0.0087(6) -0.0004(5) -0.0009(5) -0.0003(5) H43 0.0159(13) 0.0263(13) 0.0246(15) -0.0046(11) -0.0079(13) -0.0001(11) C44 0.0059(6) 0.0063(5) 0.0100(6) 0.0006(5) 0.0003(5) -0.0002(5) C45 0.0058(6) 0.0058(5) 0.0106(6) -0.0002(5) -0.0011(5) 0.0009(4) H45 0.0209(13) 0.0191(12) 0.0233(14) -0.0077(11) 0.0002(11) 0.0061(11) C46 0.0054(6) 0.0047(5) 0.0078(6) -0.0003(5) 0.0006(5) 0.0004(4) C47 0.0061(6) 0.0091(7) 0.0158(8) 0.0020(5) -0.0006(6) 0.0025(5) H471 0.0250(15) 0.053(2) 0.032(2) 0.0077(15) 0.0120(14) 0.0131(14) H472 0.0256(15) 0.0168(15) 0.073(2) 0.0123(15) 0.0061(16) 0.0034(12) H473 0.0190(15) 0.0476(19) 0.048(2) -0.0172(16) -0.0134(16) 0.0049(14) C48 0.0069(6) 0.0062(5) 0.0089(6) -0.0010(5) -0.0002(5) 0.0002(5) C49 0.0096(7) 0.0130(7) 0.0145(7) -0.0050(6) -0.0021(6) -0.0003(6) H491 0.0198(15) 0.0355(16) 0.0356(17) -0.0004(13) 0.0030(14) -0.0084(13) H492 0.0307(16) 0.0278(15) 0.0307(16) 0.0016(13) -0.0100(13) 0.0069(13) H493 0.0298(16) 0.0322(15) 0.0295(16) -0.0179(14) -0.0038(14) 0.0024(13) C50 0.0111(7) 0.0096(6) 0.0100(7) 0.0000(6) 0.0007(6) -0.0013(5) H501 0.0346(16) 0.0197(14) 0.0330(16) 0.0117(12) 0.0078(14) 0.0047(13) H502 0.0198(15) 0.0392(16) 0.0247(15) -0.0005(13) -0.0029(13) -0.0099(12) H503 0.0339(16) 0.0259(14) 0.0245(16) -0.0094(13) 0.0083(13) -0.0006(12) C51 0.0112(7) 0.0046(6) 0.0122(7) -0.0009(5) -0.0004(6) -0.0001(5) H511 0.0310(16) 0.0226(13) 0.0347(17) 0.0095(12) 0.0100(14) -0.0025(12) H512 0.0399(17) 0.0173(12) 0.0270(16) -0.0095(12) -0.0022(13) 0.0062(12) H513 0.0224(15) 0.0246(14) 0.0346(16) 0.0021(12) -0.0099(14) 0.0009(12) C52 0.0055(6) 0.0041(5) 0.0075(6) 0.0003(5) -0.0008(5) 0.0002(4) C53 0.0091(6) 0.0072(6) 0.0095(6) -0.0005(6) 0.0013(6) -0.0013(5) H531 0.0221(15) 0.0275(14) 0.0261(15) -0.0025(12) -0.0038(13) -0.0087(12) H532 0.0288(15) 0.0235(13) 0.0254(15) -0.0080(12) 0.0111(13) -0.0018(12) H533 0.0286(15) 0.0198(14) 0.0343(16) 0.0126(12) 0.0033(13) 0.0006(12) C54 0.0093(6) 0.0078(6) 0.0085(6) -0.0025(5) 0.0004(6) -0.0001(5) H541 0.0227(15) 0.0292(14) 0.0256(15) -0.0070(12) -0.0077(13) -0.0016(12) H542 0.0324(15) 0.0166(13) 0.0300(15) -0.0007(12) 0.0004(13) 0.0101(12) H543 0.0254(15) 0.0258(13) 0.0234(14) 0.0019(12) 0.0099(13) -0.0045(12) C55 0.0096(6) 0.0072(6) 0.0101(6) 0.0007(6) -0.0021(6) 0.0023(5) H551 0.0263(15) 0.0261(14) 0.0323(16) 0.0009(12) -0.0159(14) 0.0001(12) H552 0.0309(15) 0.0234(13) 0.0285(16) 0.0095(12) 0.0054(14) -0.0024(13) H553 0.0371(17) 0.0201(13) 0.0246(15) -0.0032(12) 0.0000(13) 0.0127(13) _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 C31 1.7909(19) . ? P1 C11 1.7932(19) . ? P1 C21 1.7965(18) . ? P1 C1 1.8048(19) . ? C1 C2 1.5278(18) . ? C1 H101 1.103(3) . ? C1 H102 1.091(3) . ? C2 H201 1.089(3) . ? C2 H202 1.085(4) . ? C2 H203 1.092(4) . ? C11 C16 1.3965(18) . ? C11 C12 1.4077(17) . ? C12 C13 1.3933(18) . ? C12 H12 1.083(3) . ? C13 C14 1.3976(19) . ? C13 H13 1.089(3) . ? C14 C15 1.4000(17) . ? C14 H14 1.086(3) . ? C15 C16 1.3919(18) . ? C15 H15 1.085(3) . ? C16 H16 1.080(3) . ? C21 C22 1.4026(18) . ? C21 C26 1.4048(18) . ? C22 C23 1.4005(17) . ? C22 H22 1.092(3) . ? C23 C24 1.3939(19) . ? C23 H23 1.086(3) . ? C24 C25 1.3928(19) . ? C24 H24 1.088(3) . ? C25 C26 1.3960(18) . ? C25 H25 1.090(3) . ? C26 H26 1.085(3) . ? C31 C32 1.4017(18) . ? C31 C36 1.4018(18) . ? C32 C33 1.3956(18) . ? C32 H32 1.088(3) . ? C33 C34 1.3964(18) . ? C33 H33 1.088(3) . ? C34 C35 1.3976(19) . ? C34 H34 1.087(3) . ? C35 C36 1.3940(18) . ? C35 H35 1.084(3) . ? C36 H36 1.085(3) . ? O1 C41 1.296(2) . ? C41 C42 1.4439(18) . ? C41 C46 1.4509(17) . ? C42 C43 1.4000(18) . ? C42 C48 1.5390(17) . ? C43 C44 1.3993(18) . ? C43 H43 1.090(3) . ? C44 C45 1.4005(18) . ? C44 C47 1.5095(17) . ? C45 C46 1.3888(18) . ? C45 H45 1.093(3) . ? C46 C52 1.5365(17) . ? C47 H471 1.084(4) . ? C47 H472 1.083(3) . ? C47 H473 1.086(4) . ? C48 C49 1.5340(18) . ? C48 C51 1.5412(17) . ? C48 C50 1.5438(18) . ? C49 H491 1.098(3) . ? C49 H492 1.092(3) . ? C49 H493 1.094(3) . ? C50 H501 1.094(3) . ? C50 H502 1.090(3) . ? C50 H503 1.094(3) . ? C51 H511 1.097(3) . ? C51 H512 1.094(3) . ? C51 H513 1.089(3) . ? C52 C54 1.5373(17) . ? C52 C55 1.5407(17) . ? C52 C53 1.5414(17) . ? C53 H531 1.094(3) . ? C53 H532 1.088(3) . ? C53 H533 1.094(3) . ? C54 H541 1.098(3) . ? C54 H542 1.093(3) . ? C54 H543 1.099(3) . ? C55 H551 1.099(3) . ? C55 H552 1.093(3) . ? C55 H553 1.082(3) . ? 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 C31 P1 C11 107.59(9) . . ? C31 P1 C21 109.53(10) . . ? C11 P1 C21 110.69(10) . . ? C31 P1 C1 111.66(10) . . ? C11 P1 C1 111.15(10) . . ? C21 P1 C1 106.24(9) . . ? C2 C1 P1 115.83(10) . . ? C2 C1 H101 110.93(19) . . ? P1 C1 H101 104.82(18) . . ? C2 C1 H102 111.30(19) . . ? P1 C1 H102 105.33(19) . . ? H101 C1 H102 108.1(3) . . ? C1 C2 H201 109.2(2) . . ? C1 C2 H202 111.4(2) . . ? H201 C2 H202 107.1(3) . . ? C1 C2 H203 112.3(2) . . ? H201 C2 H203 108.2(3) . . ? H202 C2 H203 108.4(3) . . ? C16 C11 C12 120.02(11) . . ? C16 C11 P1 120.38(10) . . ? C12 C11 P1 119.55(11) . . ? C13 C12 C11 119.83(12) . . ? C13 C12 H12 119.00(18) . . ? C11 C12 H12 121.16(18) . . ? C12 C13 C14 120.02(11) . . ? C12 C13 H13 119.4(2) . . ? C14 C13 H13 120.59(19) . . ? C13 C14 C15 119.99(12) . . ? C13 C14 H14 120.35(19) . . ? C15 C14 H14 119.7(2) . . ? C16 C15 C14 120.24(12) . . ? C16 C15 H15 119.56(18) . . ? C14 C15 H15 120.20(19) . . ? C15 C16 C11 119.89(11) . . ? C15 C16 H16 119.90(18) . . ? C11 C16 H16 120.22(19) . . ? C22 C21 C26 120.73(11) . . ? C22 C21 P1 118.45(10) . . ? C26 C21 P1 120.80(10) . . ? C23 C22 C21 119.11(12) . . ? C23 C22 H22 119.18(18) . . ? C21 C22 H22 121.72(18) . . ? C24 C23 C22 120.12(12) . . ? C24 C23 H23 120.89(19) . . ? C22 C23 H23 119.0(2) . . ? C25 C24 C23 120.63(11) . . ? C25 C24 H24 119.6(2) . . ? C23 C24 H24 119.7(2) . . ? C24 C25 C26 120.03(12) . . ? C24 C25 H25 120.20(19) . . ? C26 C25 H25 119.77(19) . . ? C25 C26 C21 119.38(12) . . ? C25 C26 H26 119.92(19) . . ? C21 C26 H26 120.70(19) . . ? C32 C31 C36 120.54(12) . . ? C32 C31 P1 119.21(10) . . ? C36 C31 P1 120.14(11) . . ? C33 C32 C31 119.46(11) . . ? C33 C32 H32 119.03(19) . . ? C31 C32 H32 121.50(19) . . ? C32 C33 C34 120.05(12) . . ? C32 C33 H33 119.60(19) . . ? C34 C33 H33 120.35(19) . . ? C33 C34 C35 120.38(12) . . ? C33 C34 H34 119.81(19) . . ? C35 C34 H34 119.80(19) . . ? C36 C35 C34 119.97(12) . . ? C36 C35 H35 119.75(19) . . ? C34 C35 H35 120.27(19) . . ? C35 C36 C31 119.58(12) . . ? C35 C36 H36 119.81(18) . . ? C31 C36 H36 120.62(19) . . ? O1 C41 C42 121.52(12) . . ? O1 C41 C46 121.53(12) . . ? C42 C41 C46 116.95(11) . . ? C43 C42 C41 119.93(11) . . ? C43 C42 C48 120.22(11) . . ? C41 C42 C48 119.84(11) . . ? C44 C43 C42 122.81(12) . . ? C44 C43 H43 117.27(19) . . ? C42 C43 H43 119.92(19) . . ? C43 C44 C45 117.22(11) . . ? C43 C44 C47 122.05(11) . . ? C45 C44 C47 120.70(11) . . ? C46 C45 C44 123.14(11) . . ? C46 C45 H45 119.90(19) . . ? C44 C45 H45 116.95(18) . . ? C45 C46 C41 119.93(11) . . ? C45 C46 C52 120.23(11) . . ? C41 C46 C52 119.75(11) . . ? C44 C47 H471 112.3(2) . . ? C44 C47 H472 112.6(2) . . ? H471 C47 H472 105.9(3) . . ? C44 C47 H473 111.7(2) . . ? H471 C47 H473 106.9(3) . . ? H472 C47 H473 107.1(3) . . ? C49 C48 C42 112.69(10) . . ? C49 C48 C51 106.76(10) . . ? C42 C48 C51 110.65(10) . . ? C49 C48 C50 106.87(10) . . ? C42 C48 C50 109.24(10) . . ? C51 C48 C50 110.54(10) . . ? C48 C49 H491 111.8(2) . . ? C48 C49 H492 112.6(2) . . ? H491 C49 H492 108.8(3) . . ? C48 C49 H493 109.2(2) . . ? H491 C49 H493 107.2(3) . . ? H492 C49 H493 106.9(3) . . ? C48 C50 H501 110.5(2) . . ? C48 C50 H502 110.64(19) . . ? H501 C50 H502 108.9(3) . . ? C48 C50 H503 110.70(19) . . ? H501 C50 H503 106.9(3) . . ? H502 C50 H503 109.1(3) . . ? C48 C51 H511 110.14(19) . . ? C48 C51 H512 110.39(19) . . ? H511 C51 H512 108.1(3) . . ? C48 C51 H513 111.16(18) . . ? H511 C51 H513 108.8(3) . . ? H512 C51 H513 108.2(3) . . ? C46 C52 C54 112.45(10) . . ? C46 C52 C55 111.62(10) . . ? C54 C52 C55 105.96(10) . . ? C46 C52 C53 108.46(10) . . ? C54 C52 C53 108.29(10) . . ? C55 C52 C53 109.99(10) . . ? C52 C53 H531 111.09(19) . . ? C52 C53 H532 110.05(18) . . ? H531 C53 H532 108.6(3) . . ? C52 C53 H533 110.71(19) . . ? H531 C53 H533 107.9(3) . . ? H532 C53 H533 108.4(3) . . ? C52 C54 H541 109.08(19) . . ? C52 C54 H542 112.90(19) . . ? H541 C54 H542 107.4(2) . . ? C52 C54 H543 112.04(18) . . ? H541 C54 H543 107.4(3) . . ? H542 C54 H543 107.8(3) . . ? C52 C55 H551 110.15(18) . . ? C52 C55 H552 110.00(19) . . ? H551 C55 H552 107.8(3) . . ? C52 C55 H553 111.21(19) . . ? H551 C55 H553 109.2(3) . . ? H552 C55 H553 108.4(3) . . ?