# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Vadapalli Chandrasekhar' _publ_contact_author_email VC@IITK.AC.IN _publ_section_title ; First Example of a Molecular Ce(III) Phosphonate. Synthesis, Structural Characterization and Catalytic activity of [Ce2{Ph3CPO2(OEt)}4(NO3)2(H2O)4]. Structural Diversity of Ph3CPO3H2 ; loop_ _publ_author_name 'Vadapalli Chandrasekhar' 'Palani Sasikumar' #===END data_Ce _database_code_depnum_ccdc_archive 'CCDC 680989' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'metal phosphonate' _chemical_melting_point ? _chemical_formula_moiety 'C84 H88 Ce2 N2 O22 P4' _chemical_formula_sum 'C84 H88 Ce2 N2 O22 P4' _chemical_formula_weight 1881.68 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' N N 0.0061 0.0033 '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' Ce Ce -0.2486 2.6331 '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' _symmetry_space_group_name_HALL '-P 1' _symmetry_Int_Tables_Number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7466(12) _cell_length_b 13.8798(14) _cell_length_c 15.5788(16) _cell_angle_alpha 64.601(17) _cell_angle_beta 68.103(16) _cell_angle_gamma 89.089(18) _cell_volume 2097.3(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3505 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 23.26 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 958 _exptl_absorpt_coefficient_mu 1.221 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8876 _exptl_absorpt_correction_T_max 0.9643 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11820 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.00 _reflns_number_total 8067 _reflns_number_gt 6686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Atom O9 refined isotropically due to their high thermal parameter. The electron density peak near to Ce1 atom could not be fixed. We have tried various possibilities including twinning, the possibility that P2 is disordered etc. We believe that this electron density is due to the diffraction ripple from the heavy Cerium atom. The hydrogen positions of the water molecule improved more reasonably by applying the restrains DFIX and DANG instructions. Large Non-Solvent C Ueq(max)/Ueq(min) is 3.69 ratio, since the carbon atoms present in one of the phenyl ring having the high thermal parameters 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^)+(0.1054P)^2^+5.0708P] 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_number_reflns 8067 _refine_ls_number_parameters 431 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1878 _refine_ls_wR_factor_gt 0.1731 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _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 Ce1 Ce 0.32741(3) 0.00148(3) 0.99383(3) 0.03133(15) Uani 1 1 d . . . P1 P 0.15677(16) -0.12720(15) 0.90917(15) 0.0381(4) Uani 1 1 d . . . P2 P 0.61883(19) 0.1146(2) 0.76772(15) 0.0529(5) Uani 1 1 d . . . O1 O 0.2503(4) -0.1248(4) 0.9526(4) 0.0395(11) Uani 1 1 d . . . O2 O 0.2333(5) -0.0820(4) 0.7877(4) 0.0470(12) Uani 1 1 d . . . O3 O 0.0534(5) -0.0662(5) 0.9323(4) 0.0514(13) Uani 1 1 d . . . O4 O 0.4825(4) 0.1095(4) 0.8210(3) 0.0393(11) Uani 1 1 d . . . O5 O 0.3032(4) -0.0922(4) 1.1715(4) 0.0448(12) Uani 1 1 d . . . O6 O 0.6391(6) 0.0256(5) 0.7221(5) 0.0674(16) Uani 1 1 d . . . O7 O 0.5019(4) 0.1000(4) 1.0129(4) 0.0351(10) Uani 1 1 d . . . O8 O 0.3336(5) 0.1727(4) 1.0136(4) 0.0503(13) Uani 1 1 d . A . O9 O 0.4822(15) 0.2608(13) 1.0332(12) 0.201(6) Uiso 1 1 d . A 1 O10 O 0.2005(4) 0.1207(4) 0.9020(4) 0.0372(10) Uani 1 1 d D . . O11 O 0.1033(4) -0.0515(4) 1.1246(4) 0.0422(11) Uani 1 1 d D . . N1 N 0.4368(7) 0.1728(5) 1.0182(6) 0.0550(17) Uani 1 1 d . . . C1 C 0.0912(5) -0.2696(5) 0.9519(5) 0.0344(14) Uani 1 1 d . . . C2 C 0.0349(2) -0.26583(19) 0.87317(15) 0.0402(16) Uani 1 1 d G . . C3 C -0.0551(2) -0.2017(2) 0.85910(18) 0.0459(17) Uani 1 1 d G . . H3 H -0.0850 -0.1638 0.8992 0.055 Uiso 1 1 calc R . . C4 C -0.1013(3) -0.1931(3) 0.7864(2) 0.066(3) Uani 1 1 d G . . H4 H -0.1628 -0.1493 0.7768 0.080 Uiso 1 1 calc R . . C5 C -0.0576(3) -0.2486(3) 0.7278(2) 0.078(3) Uani 1 1 d G . . H5 H -0.0893 -0.2428 0.6782 0.094 Uiso 1 1 calc R . . C6 C 0.0323(3) -0.3127(3) 0.74189(18) 0.079(3) Uani 1 1 d G . . H6 H 0.0622 -0.3507 0.7018 0.095 Uiso 1 1 calc R . . C7 C 0.0786(2) -0.3213(2) 0.81456(16) 0.055(2) Uani 1 1 d G . . H7 H 0.1401 -0.3652 0.8242 0.065 Uiso 1 1 calc R . . C8 C -0.01202(19) -0.31176(19) 1.06314(16) 0.0376(15) Uani 1 1 d G . . C9 C -0.12873(18) -0.3660(2) 1.09123(16) 0.0440(16) Uani 1 1 d G . . H9 H -0.1483 -0.3729 1.0400 0.053 Uiso 1 1 calc R . . C10 C -0.2181(2) -0.4107(3) 1.19479(17) 0.0517(19) Uani 1 1 d G . . H10 H -0.2970 -0.4481 1.2129 0.062 Uiso 1 1 calc R . . C11 C -0.1914(3) -0.4006(3) 1.27058(16) 0.054(2) Uani 1 1 d G . . H11 H -0.2514 -0.4311 1.3404 0.065 Uiso 1 1 calc R . . C12 C -0.0738(3) -0.3443(3) 1.24223(18) 0.058(2) Uani 1 1 d G . . H12 H -0.0546 -0.3355 1.2928 0.069 Uiso 1 1 calc R . . C13 C 0.0148(3) -0.3014(2) 1.13882(19) 0.0480(18) Uani 1 1 d G . . H13 H 0.0943 -0.2647 1.1204 0.058 Uiso 1 1 calc R . . C14 C 0.19240(17) -0.3407(2) 0.95269(18) 0.0369(15) Uani 1 1 d G . . C15 C 0.1670(2) -0.4463(2) 1.03197(19) 0.0431(16) Uani 1 1 d G . . H15 H 0.0875 -0.4730 1.0886 0.052 Uiso 1 1 calc R . . C16 C 0.2578(3) -0.5135(3) 1.0290(3) 0.0530(19) Uani 1 1 d G . . H16 H 0.2400 -0.5845 1.0844 0.064 Uiso 1 1 calc R . . C17 C 0.3725(3) -0.4768(3) 0.9461(3) 0.068(3) Uani 1 1 d G . . H17 H 0.4335 -0.5225 0.9440 0.082 Uiso 1 1 calc R . . C18 C 0.39838(19) -0.3713(3) 0.8648(3) 0.076(3) Uani 1 1 d G . . H18 H 0.4768 -0.3455 0.8071 0.091 Uiso 1 1 calc R . . C19 C 0.30962(17) -0.3054(3) 0.8691(2) 0.062(2) Uani 1 1 d G . . H19 H 0.3283 -0.2341 0.8140 0.074 Uiso 1 1 calc R . . C20 C 0.2020(12) 0.0024(9) 0.7130(8) 0.086(3) Uani 1 1 d . . . H20A H 0.2279 0.0731 0.7074 0.103 Uiso 1 1 calc R . . H20B H 0.1109 -0.0086 0.7331 0.103 Uiso 1 1 calc R . . C21 C 0.2689(16) -0.0003(13) 0.6122(9) 0.129(6) Uani 1 1 d . . . H21A H 0.3578 0.0016 0.5975 0.194 Uiso 1 1 calc R . . H21B H 0.2580 0.0627 0.5565 0.194 Uiso 1 1 calc R . . H21C H 0.2350 -0.0668 0.6161 0.194 Uiso 1 1 calc R . . C22 C 0.6879(8) 0.2444(7) 0.6525(6) 0.055(2) Uani 1 1 d . . . C23 C 0.8305(2) 0.2581(2) 0.5902(2) 0.0433(16) Uani 1 1 d G . . C24 C 0.8949(3) 0.1717(3) 0.6089(3) 0.067(2) Uani 1 1 d G . . H24 H 0.8509 0.1002 0.6570 0.081 Uiso 1 1 calc R . . C25 C 1.0238(3) 0.1898(4) 0.5571(4) 0.087(3) Uani 1 1 d G . . H25 H 1.0678 0.1308 0.5699 0.104 Uiso 1 1 calc R . . C26 C 1.0882(2) 0.2944(4) 0.4867(3) 0.093(4) Uani 1 1 d G . . H26 H 1.1763 0.3068 0.4513 0.112 Uiso 1 1 calc R . . C27 C 1.0238(2) 0.3808(4) 0.4680(3) 0.096(4) Uani 1 1 d G . . H27 H 1.0678 0.4522 0.4198 0.115 Uiso 1 1 calc R . . C28 C 0.8949(2) 0.3626(3) 0.5198(2) 0.077(3) Uani 1 1 d G . . H28 H 0.8509 0.4217 0.5070 0.092 Uiso 1 1 calc R . . C29 C 0.6628(2) 0.3248(2) 0.70185(19) 0.060(2) Uani 1 1 d G . . C30 C 0.7264(3) 0.3328(3) 0.7574(2) 0.0502(18) Uani 1 1 d G . . H30 H 0.7778 0.2805 0.7743 0.060 Uiso 1 1 calc R . . C31 C 0.7217(3) 0.4089(4) 0.7897(3) 0.072(3) Uani 1 1 d G . . H31 H 0.7646 0.4063 0.8315 0.087 Uiso 1 1 calc R . . C32 C 0.6565(4) 0.4886(4) 0.7631(3) 0.071(3) Uani 1 1 d G . . H32 H 0.6511 0.5408 0.7881 0.086 Uiso 1 1 calc R . . C33 C 0.5966(3) 0.4952(3) 0.6989(3) 0.083(3) Uani 1 1 d G . . H33 H 0.5518 0.5525 0.6791 0.100 Uiso 1 1 calc R . . C34 C 0.6032(3) 0.4160(2) 0.6636(3) 0.076(3) Uani 1 1 d G . . H34 H 0.5687 0.4227 0.6154 0.091 Uiso 1 1 calc R . . C35 C 0.6204(2) 0.2526(2) 0.5789(2) 0.0516(19) Uani 1 1 d G . . C36 C 0.6784(3) 0.2500(3) 0.4873(2) 0.064(2) Uani 1 1 d G . . H36 H 0.7640 0.2436 0.4643 0.076 Uiso 1 1 calc R . . C37 C 0.6151(4) 0.2564(3) 0.4259(3) 0.080(3) Uani 1 1 d G . . H37 H 0.6572 0.2565 0.3606 0.096 Uiso 1 1 calc R . . C38 C 0.4917(4) 0.2627(4) 0.4607(3) 0.096(4) Uani 1 1 d G . . H38 H 0.4485 0.2666 0.4187 0.115 Uiso 1 1 calc R . . C39 C 0.4275(3) 0.2636(4) 0.5536(3) 0.080(3) Uani 1 1 d G . . H39 H 0.3406 0.2647 0.5774 0.096 Uiso 1 1 calc R . . C40 C 0.4934(2) 0.2630(3) 0.6139(3) 0.057(2) Uani 1 1 d G . . H40 H 0.4532 0.2693 0.6762 0.068 Uiso 1 1 calc R . . C41 C 0.5476(11) -0.0186(7) 0.7060(8) 0.073(3) Uani 1 1 d . . . H41A H 0.5258 0.0386 0.6523 0.088 Uiso 1 1 calc R . . H41B H 0.4715 -0.0533 0.7712 0.088 Uiso 1 1 calc R . . C42 C 0.5993(11) -0.0990(10) 0.6719(9) 0.103(5) Uani 1 1 d . . . H42A H 0.6802 -0.0658 0.6129 0.154 Uiso 1 1 calc R . . H42B H 0.5423 -0.1250 0.6508 0.154 Uiso 1 1 calc R . . H42C H 0.6099 -0.1600 0.7292 0.154 Uiso 1 1 calc R . . H101 H 0.130(5) 0.084(8) 0.911(8) 0.10(4) Uiso 1 1 d D . . H102 H 0.182(9) 0.149(10) 0.948(8) 0.14(6) Uiso 1 1 d D . . H103 H 0.046(5) -0.008(5) 1.113(5) 0.06(3) Uiso 1 1 d D . . H104 H 0.070(6) -0.096(5) 1.1956(19) 0.05(2) Uiso 1 1 d 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 Ce1 0.0342(2) 0.0322(2) 0.0352(2) -0.01638(17) -0.02069(16) 0.00835(15) P1 0.0360(9) 0.0435(10) 0.0527(11) -0.0306(9) -0.0260(8) 0.0127(7) P2 0.0419(11) 0.0744(15) 0.0350(10) -0.0139(10) -0.0211(8) 0.0058(10) O1 0.037(2) 0.043(3) 0.057(3) -0.032(2) -0.028(2) 0.016(2) O2 0.047(3) 0.048(3) 0.045(3) -0.020(2) -0.019(2) 0.006(2) O3 0.046(3) 0.072(4) 0.077(4) -0.055(3) -0.042(3) 0.032(3) O4 0.037(2) 0.047(3) 0.032(2) -0.011(2) -0.021(2) 0.003(2) O5 0.036(2) 0.062(3) 0.033(2) -0.014(2) -0.018(2) 0.006(2) O6 0.077(4) 0.059(4) 0.074(4) -0.028(3) -0.041(3) 0.011(3) O7 0.037(2) 0.036(2) 0.046(3) -0.024(2) -0.025(2) 0.0132(19) O8 0.044(3) 0.055(3) 0.076(4) -0.038(3) -0.039(3) 0.024(2) O10 0.035(2) 0.036(3) 0.038(3) -0.011(2) -0.018(2) 0.004(2) O11 0.041(3) 0.052(3) 0.033(3) -0.017(2) -0.018(2) 0.017(2) N1 0.071(5) 0.049(4) 0.068(5) -0.036(4) -0.040(4) 0.021(3) C1 0.025(3) 0.042(4) 0.040(4) -0.024(3) -0.011(3) 0.000(3) C2 0.032(3) 0.053(4) 0.033(3) -0.025(3) -0.004(3) -0.008(3) C3 0.038(4) 0.060(5) 0.041(4) -0.022(4) -0.018(3) -0.004(3) C4 0.048(5) 0.097(7) 0.046(5) -0.023(5) -0.021(4) -0.018(5) C5 0.070(6) 0.116(9) 0.044(5) -0.031(5) -0.024(5) -0.023(6) C6 0.066(6) 0.121(9) 0.046(5) -0.054(6) 0.002(4) -0.031(6) C7 0.042(4) 0.073(5) 0.047(4) -0.035(4) -0.006(3) -0.011(4) C8 0.034(3) 0.050(4) 0.038(4) -0.026(3) -0.017(3) 0.015(3) C9 0.037(4) 0.058(4) 0.040(4) -0.026(3) -0.014(3) 0.011(3) C10 0.037(4) 0.058(5) 0.052(5) -0.022(4) -0.013(3) 0.005(3) C11 0.058(5) 0.066(5) 0.035(4) -0.024(4) -0.013(3) 0.017(4) C12 0.059(5) 0.086(6) 0.043(4) -0.038(4) -0.025(4) 0.018(4) C13 0.041(4) 0.068(5) 0.048(4) -0.037(4) -0.019(3) 0.018(4) C14 0.032(3) 0.038(4) 0.048(4) -0.028(3) -0.013(3) 0.003(3) C15 0.044(4) 0.050(4) 0.045(4) -0.030(4) -0.018(3) 0.006(3) C16 0.065(5) 0.051(5) 0.061(5) -0.034(4) -0.035(4) 0.023(4) C17 0.053(5) 0.067(6) 0.100(7) -0.053(6) -0.029(5) 0.023(4) C18 0.047(5) 0.065(6) 0.102(8) -0.039(6) -0.016(5) 0.019(4) C19 0.038(4) 0.036(4) 0.085(6) -0.025(4) -0.001(4) 0.004(3) C20 0.109(9) 0.070(7) 0.059(6) -0.015(5) -0.031(6) 0.027(6) C21 0.201(16) 0.139(12) 0.058(7) -0.046(8) -0.062(9) 0.072(12) C22 0.054(5) 0.060(5) 0.041(4) -0.010(4) -0.025(4) 0.005(4) C23 0.036(4) 0.053(4) 0.037(4) -0.018(3) -0.014(3) 0.004(3) C24 0.061(5) 0.078(6) 0.042(5) -0.016(4) -0.013(4) 0.021(5) C25 0.072(7) 0.110(9) 0.057(6) -0.029(6) -0.017(5) 0.031(6) C26 0.051(6) 0.145(12) 0.086(8) -0.064(8) -0.017(5) 0.000(7) C27 0.087(7) 0.081(7) 0.074(7) -0.051(6) 0.034(6) -0.039(6) C28 0.075(6) 0.053(5) 0.065(6) -0.026(5) 0.008(5) 0.002(4) C29 0.061(5) 0.072(6) 0.093(7) -0.059(5) -0.053(5) 0.033(4) C30 0.052(4) 0.056(5) 0.047(4) -0.023(4) -0.025(4) 0.011(4) C31 0.066(6) 0.101(8) 0.069(6) -0.056(6) -0.026(5) 0.016(5) C32 0.063(6) 0.080(7) 0.086(7) -0.046(6) -0.037(5) 0.012(5) C33 0.078(7) 0.071(7) 0.100(8) -0.043(6) -0.032(6) 0.021(5) C34 0.073(6) 0.084(7) 0.087(7) -0.046(6) -0.042(6) 0.020(5) C35 0.043(4) 0.054(5) 0.035(4) 0.002(3) -0.019(3) -0.003(3) C36 0.068(6) 0.051(5) 0.048(5) -0.008(4) -0.015(4) 0.007(4) C37 0.082(7) 0.094(8) 0.060(6) -0.045(6) -0.012(5) -0.018(6) C38 0.106(9) 0.125(10) 0.072(7) -0.038(7) -0.061(7) 0.005(8) C39 0.079(7) 0.099(8) 0.055(6) -0.020(5) -0.038(5) 0.002(6) C40 0.062(5) 0.066(5) 0.057(5) -0.028(4) -0.040(4) 0.020(4) C41 0.124(9) 0.046(5) 0.066(6) -0.021(4) -0.062(6) 0.006(5) C42 0.104(9) 0.099(9) 0.092(8) -0.064(7) -0.001(7) -0.035(7) _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 Ce1 O1 2.399(4) . ? Ce1 O5 2.402(5) . ? Ce1 O4 2.405(5) . ? Ce1 O7 2.427(4) 2_657 ? Ce1 O8 2.529(5) . ? Ce1 O11 2.529(5) . ? Ce1 O10 2.547(5) . ? Ce1 O7 2.656(4) . ? Ce1 N1 2.947(6) . ? Ce1 Ce1 4.1291(8) 2_657 ? P1 O3 1.492(5) . ? P1 O1 1.497(5) . ? P1 O2 1.585(5) . ? P1 C1 1.865(6) . ? P2 O5 1.489(5) 2_657 ? P2 O4 1.490(5) . ? P2 O6 1.645(7) . ? P2 C22 1.820(8) . ? O2 C20 1.414(11) . ? O5 P2 1.489(5) 2_657 ? O6 C41 1.396(11) . ? O7 N1 1.270(8) . ? O7 Ce1 2.427(4) 2_657 ? O8 N1 1.242(8) . ? O9 N1 1.479(17) . ? O10 H101 0.91(2) . ? O10 H102 0.91(2) . ? O11 H103 0.92(2) . ? O11 H104 0.93(2) . ? C1 C14 1.533(7) . ? C1 C8 1.549(6) . ? C1 C2 1.580(7) . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C3 H3 0.9500 . ? C4 C5 1.3900 . ? C4 H4 0.9500 . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 C7 1.3900 . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.3913 . ? C8 C9 1.3928 . ? C9 C10 1.4102 . ? C9 H9 0.9500 . ? C10 C11 1.3900 . ? C10 H10 0.9500 . ? C11 C12 1.4139 . ? C11 H11 0.9500 . ? C12 C13 1.4069 . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.3957 . ? C14 C19 1.4027 . ? C15 C16 1.4065 . ? C15 H15 0.9500 . ? C16 C17 1.3791 . ? C16 H16 0.9500 . ? C17 C18 1.4069 . ? C17 H17 0.9500 . ? C18 C19 1.3777 . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.488(15) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.557(9) . ? C22 C29 1.575(9) . ? C22 C35 1.587(8) . ? C23 C24 1.3900 . ? C23 C28 1.3900 . ? C24 C25 1.3900 . ? C24 H24 0.9500 . ? C25 C26 1.3900 . ? C25 H25 0.9500 . ? C26 C27 1.3900 . ? C26 H26 0.9500 . ? C27 C28 1.3900 . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.3742 . ? C29 C34 1.4436 . ? C30 C31 1.3435 . ? C30 H30 0.9500 . ? C31 C32 1.3402 . ? C31 H31 0.9500 . ? C32 C33 1.3944 . ? C32 H32 0.9500 . ? C33 C34 1.4157 . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C36 1.3499 . ? C35 C40 1.4125 . ? C36 C37 1.3898 . ? C36 H36 0.9500 . ? C37 C38 1.3610 . ? C37 H37 0.9500 . ? C38 C39 1.3662 . ? C38 H38 0.9500 . ? C39 C40 1.4197 . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C42 1.463(14) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? 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 Ce1 O5 108.23(17) . . ? O1 Ce1 O4 95.35(16) . . ? O5 Ce1 O4 141.45(15) . . ? O1 Ce1 O7 83.03(15) . 2_657 ? O5 Ce1 O7 76.08(16) . 2_657 ? O4 Ce1 O7 77.08(16) . 2_657 ? O1 Ce1 O8 154.42(16) . . ? O5 Ce1 O8 86.04(18) . . ? O4 Ce1 O8 85.02(17) . . ? O7 Ce1 O8 121.68(15) 2_657 . ? O1 Ce1 O11 79.93(16) . . ? O5 Ce1 O11 66.14(16) . . ? O4 Ce1 O11 150.25(16) . . ? O7 Ce1 O11 130.56(16) 2_657 . ? O8 Ce1 O11 87.12(17) . . ? O1 Ce1 O10 82.05(16) . . ? O5 Ce1 O10 134.51(16) . . ? O4 Ce1 O10 77.52(15) . . ? O7 Ce1 O10 149.06(15) 2_657 . ? O8 Ce1 O10 73.03(16) . . ? O11 Ce1 O10 72.75(15) . . ? O1 Ce1 O7 153.71(14) . . ? O5 Ce1 O7 72.14(15) . . ? O4 Ce1 O7 73.36(15) . . ? O7 Ce1 O7 71.43(15) 2_657 . ? O8 Ce1 O7 50.25(14) . . ? O11 Ce1 O7 121.51(15) . . ? O10 Ce1 O7 117.13(14) . . ? O1 Ce1 N1 173.35(18) . . ? O5 Ce1 N1 78.14(19) . . ? O4 Ce1 N1 78.20(18) . . ? O7 Ce1 N1 96.96(17) 2_657 . ? O8 Ce1 N1 24.73(17) . . ? O11 Ce1 N1 104.85(19) . . ? O10 Ce1 N1 94.85(17) . . ? O7 Ce1 N1 25.53(16) . . ? O1 Ce1 Ce1 120.35(11) . 2_657 ? O5 Ce1 Ce1 70.21(11) . 2_657 ? O4 Ce1 Ce1 71.61(11) . 2_657 ? O7 Ce1 Ce1 37.57(10) 2_657 2_657 ? O8 Ce1 Ce1 84.12(11) . 2_657 ? O11 Ce1 Ce1 135.92(11) . 2_657 ? O10 Ce1 Ce1 142.89(10) . 2_657 ? O7 Ce1 Ce1 33.87(9) . 2_657 ? N1 Ce1 Ce1 59.39(14) . 2_657 ? O3 P1 O1 115.4(3) . . ? O3 P1 O2 111.2(3) . . ? O1 P1 O2 106.0(3) . . ? O3 P1 C1 109.8(3) . . ? O1 P1 C1 110.5(3) . . ? O2 P1 C1 103.3(3) . . ? O5 P2 O4 118.9(3) 2_657 . ? O5 P2 O6 105.5(3) 2_657 . ? O4 P2 O6 108.4(3) . . ? O5 P2 C22 108.3(3) 2_657 . ? O4 P2 C22 110.4(4) . . ? O6 P2 C22 104.2(4) . . ? P1 O1 Ce1 134.7(3) . . ? C20 O2 P1 123.2(6) . . ? P2 O4 Ce1 134.5(3) . . ? P2 O5 Ce1 138.9(3) 2_657 . ? C41 O6 P2 123.9(6) . . ? N1 O7 Ce1 161.2(4) . 2_657 ? N1 O7 Ce1 90.2(4) . . ? Ce1 O7 Ce1 108.57(15) 2_657 . ? N1 O8 Ce1 96.8(4) . . ? Ce1 O10 H101 114(7) . . ? Ce1 O10 H102 88(9) . . ? H101 O10 H102 110(5) . . ? Ce1 O11 H103 121(4) . . ? Ce1 O11 H104 130(4) . . ? H103 O11 H104 106(4) . . ? O8 N1 O7 122.7(6) . . ? O8 N1 O9 117.4(8) . . ? O7 N1 O9 119.8(9) . . ? O8 N1 Ce1 58.4(3) . . ? O7 N1 Ce1 64.3(3) . . ? O9 N1 Ce1 175.6(8) . . ? C14 C1 C8 109.9(4) . . ? C14 C1 C2 111.0(4) . . ? C8 C1 C2 110.9(4) . . ? C14 C1 P1 110.9(3) . . ? C8 C1 P1 107.2(3) . . ? C2 C1 P1 106.8(4) . . ? C3 C2 C7 120.0 . . ? C3 C2 C1 119.1(2) . . ? C7 C2 C1 120.8(2) . . ? C2 C3 C4 120.0 . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.0 . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.0 . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C2 120.0 . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? C13 C8 C9 118.9 . . ? C13 C8 C1 119.2(2) . . ? C9 C8 C1 121.8(2) . . ? C8 C9 C10 120.8 . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 120.4 . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.1 . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C13 C12 C11 119.7 . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C8 C13 C12 121.1 . . ? C8 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C19 117.8 . . ? C15 C14 C1 120.9(2) . . ? C19 C14 C1 121.0(3) . . ? C14 C15 C16 120.7 . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 120.4 . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.4 . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 119.8 . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C14 121.8 . . ? C18 C19 H19 119.1 . . ? C14 C19 H19 119.1 . . ? O2 C20 C21 107.0(9) . . ? O2 C20 H20A 110.3 . . ? C21 C20 H20A 110.3 . . ? O2 C20 H20B 110.3 . . ? C21 C20 H20B 110.3 . . ? H20A C20 H20B 108.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C29 109.3(5) . . ? C23 C22 C35 108.0(5) . . ? C29 C22 C35 117.3(6) . . ? C23 C22 P2 114.7(5) . . ? C29 C22 P2 101.3(4) . . ? C35 C22 P2 106.3(5) . . ? C24 C23 C28 120.0 . . ? C24 C23 C22 122.4(3) . . ? C28 C23 C22 117.4(3) . . ? C25 C24 C23 120.0 . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.0 . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 120.0 . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 120.0 . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C27 C28 C23 120.0 . . ? C27 C28 H28 120.0 . . ? C23 C28 H28 120.0 . . ? C30 C29 C34 114.9 . . ? C30 C29 C22 122.2(3) . . ? C34 C29 C22 120.1(3) . . ? C31 C30 C29 125.2 . . ? C31 C30 H30 117.4 . . ? C29 C30 H30 117.4 . . ? C32 C31 C30 120.1 . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C31 C32 C33 120.4 . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C32 C33 C34 119.5 . . ? C32 C33 H33 120.3 . . ? C34 C33 H33 120.3 . . ? C33 C34 C29 119.2 . . ? C33 C34 H34 120.4 . . ? C29 C34 H34 120.4 . . ? C36 C35 C40 120.3 . . ? C36 C35 C22 123.2(3) . . ? C40 C35 C22 116.6(3) . . ? C35 C36 C37 121.1 . . ? C35 C36 H36 119.5 . . ? C37 C36 H36 119.5 . . ? C38 C37 C36 119.0 . . ? C38 C37 H37 120.5 . . ? C36 C37 H37 120.5 . . ? C37 C38 C39 122.5 . . ? C37 C38 H38 118.7 . . ? C39 C38 H38 118.7 . . ? C38 C39 C40 118.6 . . ? C38 C39 H39 120.7 . . ? C40 C39 H39 120.7 . . ? C35 C40 C39 118.3 . . ? C35 C40 H40 120.8 . . ? C39 C40 H40 120.8 . . ? O6 C41 C42 106.9(10) . . ? O6 C41 H41A 110.3 . . ? C42 C41 H41A 110.3 . . ? O6 C41 H41B 110.3 . . ? C42 C41 H41B 110.3 . . ? H41A C41 H41B 108.6 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? 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 O3 P1 O1 Ce1 -29.0(5) . . . . ? O2 P1 O1 Ce1 94.5(4) . . . . ? C1 P1 O1 Ce1 -154.3(4) . . . . ? O5 Ce1 O1 P1 126.0(4) . . . . ? O4 Ce1 O1 P1 -84.9(4) . . . . ? O7 Ce1 O1 P1 -161.1(4) 2_657 . . . ? O8 Ce1 O1 P1 4.8(7) . . . . ? O11 Ce1 O1 P1 65.5(4) . . . . ? O10 Ce1 O1 P1 -8.3(4) . . . . ? O7 Ce1 O1 P1 -147.5(3) . . . . ? N1 Ce1 O1 P1 -70.9(16) . . . . ? Ce1 Ce1 O1 P1 -156.7(3) 2_657 . . . ? O3 P1 O2 C20 -2.4(8) . . . . ? O1 P1 O2 C20 -128.5(8) . . . . ? C1 P1 O2 C20 115.2(8) . . . . ? O5 P2 O4 Ce1 -33.8(5) 2_657 . . . ? O6 P2 O4 Ce1 86.6(4) . . . . ? C22 P2 O4 Ce1 -159.9(4) . . . . ? O1 Ce1 O4 P2 -98.0(4) . . . . ? O5 Ce1 O4 P2 30.5(6) . . . . ? O7 Ce1 O4 P2 -16.4(4) 2_657 . . . ? O8 Ce1 O4 P2 107.7(4) . . . . ? O11 Ce1 O4 P2 -177.0(3) . . . . ? O10 Ce1 O4 P2 -178.6(4) . . . . ? O7 Ce1 O4 P2 57.8(4) . . . . ? N1 Ce1 O4 P2 83.7(4) . . . . ? Ce1 Ce1 O4 P2 22.3(3) 2_657 . . . ? O1 Ce1 O5 P2 123.7(5) . . . 2_657 ? O4 Ce1 O5 P2 -1.1(7) . . . 2_657 ? O7 Ce1 O5 P2 46.0(5) 2_657 . . 2_657 ? O8 Ce1 O5 P2 -78.0(5) . . . 2_657 ? O11 Ce1 O5 P2 -166.6(6) . . . 2_657 ? O10 Ce1 O5 P2 -139.5(4) . . . 2_657 ? O7 Ce1 O5 P2 -28.7(5) . . . 2_657 ? N1 Ce1 O5 P2 -54.4(5) . . . 2_657 ? Ce1 Ce1 O5 P2 7.1(4) 2_657 . . 2_657 ? O5 P2 O6 C41 147.7(7) 2_657 . . . ? O4 P2 O6 C41 19.2(8) . . . . ? C22 P2 O6 C41 -98.3(7) . . . . ? O1 Ce1 O7 N1 164.8(4) . . . . ? O5 Ce1 O7 N1 -100.0(4) . . . . ? O4 Ce1 O7 N1 97.5(4) . . . . ? O7 Ce1 O7 N1 179.1(5) 2_657 . . . ? O8 Ce1 O7 N1 0.0(4) . . . . ? O11 Ce1 O7 N1 -54.1(4) . . . . ? O10 Ce1 O7 N1 31.5(4) . . . . ? Ce1 Ce1 O7 N1 179.1(5) 2_657 . . . ? O1 Ce1 O7 Ce1 -14.3(4) . . . 2_657 ? O5 Ce1 O7 Ce1 80.9(2) . . . 2_657 ? O4 Ce1 O7 Ce1 -81.62(19) . . . 2_657 ? O7 Ce1 O7 Ce1 0.0 2_657 . . 2_657 ? O8 Ce1 O7 Ce1 -179.1(3) . . . 2_657 ? O11 Ce1 O7 Ce1 126.78(18) . . . 2_657 ? O10 Ce1 O7 Ce1 -147.62(16) . . . 2_657 ? N1 Ce1 O7 Ce1 -179.1(5) . . . 2_657 ? O1 Ce1 O8 N1 -164.4(4) . . . . ? O5 Ce1 O8 N1 70.0(5) . . . . ? O4 Ce1 O8 N1 -72.4(5) . . . . ? O7 Ce1 O8 N1 -1.0(5) 2_657 . . . ? O11 Ce1 O8 N1 136.3(5) . . . . ? O10 Ce1 O8 N1 -150.9(5) . . . . ? O7 Ce1 O8 N1 0.0(4) . . . . ? Ce1 Ce1 O8 N1 -0.5(4) 2_657 . . . ? Ce1 O8 N1 O7 0.0(8) . . . . ? Ce1 O8 N1 O9 -178.5(8) . . . . ? Ce1 O7 N1 O8 177.4(9) 2_657 . . . ? Ce1 O7 N1 O8 0.0(7) . . . . ? Ce1 O7 N1 O9 -4(2) 2_657 . . . ? Ce1 O7 N1 O9 178.4(9) . . . . ? Ce1 O7 N1 Ce1 177.4(14) 2_657 . . . ? O1 Ce1 N1 O8 89.7(15) . . . . ? O5 Ce1 N1 O8 -106.7(5) . . . . ? O4 Ce1 N1 O8 104.0(5) . . . . ? O7 Ce1 N1 O8 179.2(4) 2_657 . . . ? O11 Ce1 N1 O8 -45.6(5) . . . . ? O10 Ce1 N1 O8 27.8(5) . . . . ? O7 Ce1 N1 O8 -180.0(7) . . . . ? Ce1 Ce1 N1 O8 179.5(5) 2_657 . . . ? O1 Ce1 N1 O7 -90.3(15) . . . . ? O5 Ce1 N1 O7 73.3(4) . . . . ? O4 Ce1 N1 O7 -76.0(4) . . . . ? O7 Ce1 N1 O7 -0.8(5) 2_657 . . . ? O8 Ce1 N1 O7 180.0(7) . . . . ? O11 Ce1 N1 O7 134.4(4) . . . . ? O10 Ce1 N1 O7 -152.2(4) . . . . ? Ce1 Ce1 N1 O7 -0.6(3) 2_657 . . . ? O1 Ce1 N1 O9 108(10) . . . . ? O5 Ce1 N1 O9 -89(10) . . . . ? O4 Ce1 N1 O9 122(10) . . . . ? O7 Ce1 N1 O9 -163(10) 2_657 . . . ? O8 Ce1 N1 O9 18(10) . . . . ? O11 Ce1 N1 O9 -28(10) . . . . ? O10 Ce1 N1 O9 46(10) . . . . ? O7 Ce1 N1 O9 -162(10) . . . . ? Ce1 Ce1 N1 O9 -163(10) 2_657 . . . ? O3 P1 C1 C14 -166.9(4) . . . . ? O1 P1 C1 C14 -38.6(5) . . . . ? O2 P1 C1 C14 74.4(4) . . . . ? O3 P1 C1 C8 -46.9(5) . . . . ? O1 P1 C1 C8 81.4(4) . . . . ? O2 P1 C1 C8 -165.5(3) . . . . ? O3 P1 C1 C2 72.0(4) . . . . ? O1 P1 C1 C2 -159.6(3) . . . . ? O2 P1 C1 C2 -46.6(4) . . . . ? C14 C1 C2 C3 -177.6(2) . . . . ? C8 C1 C2 C3 59.9(5) . . . . ? P1 C1 C2 C3 -56.6(3) . . . . ? C14 C1 C2 C7 -0.8(5) . . . . ? C8 C1 C2 C7 -123.3(3) . . . . ? P1 C1 C2 C7 120.2(3) . . . . ? C7 C2 C3 C4 0.0 . . . . ? C1 C2 C3 C4 176.8(3) . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C7 0.0 . . . . ? C5 C6 C7 C2 0.0 . . . . ? C3 C2 C7 C6 0.0 . . . . ? C1 C2 C7 C6 -176.8(3) . . . . ? C14 C1 C8 C13 69.1(4) . . . . ? C2 C1 C8 C13 -167.8(2) . . . . ? P1 C1 C8 C13 -51.5(4) . . . . ? C14 C1 C8 C9 -106.7(3) . . . . ? C2 C1 C8 C9 16.4(5) . . . . ? P1 C1 C8 C9 132.6(2) . . . . ? C13 C8 C9 C10 -0.7 . . . . ? C1 C8 C9 C10 175.2(3) . . . . ? C8 C9 C10 C11 0.6 . . . . ? C9 C10 C11 C12 0.4 . . . . ? C10 C11 C12 C13 -1.2 . . . . ? C9 C8 C13 C12 -0.2 . . . . ? C1 C8 C13 C12 -176.2(3) . . . . ? C11 C12 C13 C8 1.1 . . . . ? C8 C1 C14 C15 21.9(5) . . . . ? C2 C1 C14 C15 -101.2(4) . . . . ? P1 C1 C14 C15 140.3(2) . . . . ? C8 C1 C14 C19 -164.0(2) . . . . ? C2 C1 C14 C19 72.9(4) . . . . ? P1 C1 C14 C19 -45.6(4) . . . . ? C19 C14 C15 C16 1.7 . . . . ? C1 C14 C15 C16 176.0(3) . . . . ? C14 C15 C16 C17 -1.6 . . . . ? C15 C16 C17 C18 0.4 . . . . ? C16 C17 C18 C19 0.6 . . . . ? C17 C18 C19 C14 -0.4 . . . . ? C15 C14 C19 C18 -0.7 . . . . ? C1 C14 C19 C18 -175.0(3) . . . . ? P1 O2 C20 C21 -163.6(9) . . . . ? O5 P2 C22 C23 48.6(6) 2_657 . . . ? O4 P2 C22 C23 -179.6(4) . . . . ? O6 P2 C22 C23 -63.4(6) . . . . ? O5 P2 C22 C29 -69.0(5) 2_657 . . . ? O4 P2 C22 C29 62.8(5) . . . . ? O6 P2 C22 C29 179.0(4) . . . . ? O5 P2 C22 C35 167.9(4) 2_657 . . . ? O4 P2 C22 C35 -60.3(5) . . . . ? O6 P2 C22 C35 55.9(5) . . . . ? C29 C22 C23 C24 125.0(4) . . . . ? C35 C22 C23 C24 -106.2(4) . . . . ? P2 C22 C23 C24 12.1(6) . . . . ? C29 C22 C23 C28 -49.8(5) . . . . ? C35 C22 C23 C28 79.0(5) . . . . ? P2 C22 C23 C28 -162.7(3) . . . . ? C28 C23 C24 C25 0.0 . . . . ? C22 C23 C24 C25 -174.7(4) . . . . ? C23 C24 C25 C26 0.0 . . . . ? C24 C25 C26 C27 0.0 . . . . ? C25 C26 C27 C28 0.0 . . . . ? C26 C27 C28 C23 0.0 . . . . ? C24 C23 C28 C27 0.0 . . . . ? C22 C23 C28 C27 174.9(3) . . . . ? C23 C22 C29 C30 -49.4(6) . . . . ? C35 C22 C29 C30 -172.8(3) . . . . ? P2 C22 C29 C30 72.0(4) . . . . ? C23 C22 C29 C34 110.6(4) . . . . ? C35 C22 C29 C34 -12.9(7) . . . . ? P2 C22 C29 C34 -128.0(3) . . . . ? C34 C29 C30 C31 9.9 . . . . ? C22 C29 C30 C31 170.7(4) . . . . ? C29 C30 C31 C32 -3.8 . . . . ? C30 C31 C32 C33 -2.2 . . . . ? C31 C32 C33 C34 1.2 . . . . ? C32 C33 C34 C29 5.2 . . . . ? C30 C29 C34 C33 -10.2 . . . . ? C22 C29 C34 C33 -171.5(4) . . . . ? C23 C22 C35 C36 11.9(7) . . . . ? C29 C22 C35 C36 136.0(4) . . . . ? P2 C22 C35 C36 -111.7(4) . . . . ? C23 C22 C35 C40 -168.2(3) . . . . ? C29 C22 C35 C40 -44.2(6) . . . . ? P2 C22 C35 C40 68.2(5) . . . . ? C40 C35 C36 C37 -0.5 . . . . ? C22 C35 C36 C37 179.4(4) . . . . ? C35 C36 C37 C38 -1.7 . . . . ? C36 C37 C38 C39 0.4 . . . . ? C37 C38 C39 C40 2.9 . . . . ? C36 C35 C40 C39 3.8 . . . . ? C22 C35 C40 C39 -176.0(4) . . . . ? C38 C39 C40 C35 -5.0 . . . . ? P2 O6 C41 C42 -176.2(7) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 3.626 _refine_diff_density_min -1.518 _refine_diff_density_rms 0.153 #===END # Attachment 'Ce2_VC.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 688586' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'phosphonic acid' _chemical_melting_point ? _chemical_formula_moiety '3(C19 H17 O3 P1), C H2 Cl2' _chemical_formula_sum 'C19.33 H17.67 Cl0.67 O3 P' _chemical_formula_weight 352.60 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_HALL '-P 1' _symmetry_Int_Tables_Number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.2208(10) _cell_length_b 15.0596(10) _cell_length_c 15.4041(10) _cell_angle_alpha 113.7143(12) _cell_angle_beta 95.8743(11) _cell_angle_gamma 115.6880(10) _cell_volume 2564.3(3) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4202 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.17 _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9593 _exptl_absorpt_correction_T_max 0.9753 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14501 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 26.00 _reflns_number_total 9856 _reflns_number_gt 8005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0708P)^2^+1.0736P] 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_number_reflns 9856 _refine_ls_number_parameters 658 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.88865(5) 0.36261(5) 0.61066(4) 0.01399(15) Uani 1 1 d . . . P2 P 0.76595(5) 0.35594(5) 0.31344(4) 0.01266(14) Uani 1 1 d . . . P3 P 0.09788(5) 0.32747(5) 0.39334(5) 0.01560(15) Uani 1 1 d . . . O1 O 1.00001(13) 0.37798(13) 0.60810(12) 0.0172(4) Uani 1 1 d . . . O2 O 0.80258(13) 0.29410(14) 0.50378(12) 0.0188(4) Uani 1 1 d . . . H2 H 0.8244 0.3277 0.4726 0.028 Uiso 1 1 calc R . . O3 O 0.89785(14) 0.47838(13) 0.66981(12) 0.0196(4) Uani 1 1 d . . . H3 H 0.9224 0.5164 0.6427 0.029 Uiso 1 1 calc R . . O4 O 0.85857(13) 0.35501(13) 0.36962(12) 0.0158(3) Uani 1 1 d . . . O5 O 0.80775(13) 0.44933(13) 0.28367(12) 0.0170(4) Uani 1 1 d . . . H5 H 0.8461 0.5119 0.3346 0.026 Uiso 1 1 calc R . . O6 O 0.69386(13) 0.37381(14) 0.38071(12) 0.0175(4) Uani 1 1 d . . . H6 H 0.7323 0.4346 0.4333 0.026 Uiso 1 1 calc R . . O7 O 0.17460(13) 0.45320(14) 0.43576(12) 0.0189(4) Uani 1 1 d . . . O8 O -0.01220(14) 0.28495(14) 0.31762(13) 0.0239(4) Uani 1 1 d . . . H8 H -0.0419 0.3185 0.3462 0.036 Uiso 1 1 calc R . . O9 O 0.07888(15) 0.29559(15) 0.47630(13) 0.0247(4) Uani 1 1 d . . . H9 H 0.0514 0.3285 0.5102 0.037 Uiso 1 1 calc R . . C1 C 0.83026(18) 0.28111(19) 0.67447(17) 0.0146(5) Uani 1 1 d . . . C2 C 0.92627(18) 0.3232(2) 0.76598(17) 0.0144(5) Uani 1 1 d . . . C3 C 0.9388(2) 0.2474(2) 0.78820(19) 0.0195(5) Uani 1 1 d . . . H92 H 0.8929 0.1697 0.7441 0.023 Uiso 1 1 calc R . . C4 C 1.0190(2) 0.2864(2) 0.87556(19) 0.0227(6) Uani 1 1 d . . . H4 H 1.0263 0.2347 0.8896 0.027 Uiso 1 1 calc R . . C5 C 1.0881(2) 0.4016(2) 0.94176(19) 0.0227(6) Uani 1 1 d . . . H93 H 1.1417 0.4277 1.0004 0.027 Uiso 1 1 calc R . . C6 C 1.0768(2) 0.4780(2) 0.92004(18) 0.0211(5) Uani 1 1 d . . . H61 H 1.1235 0.5557 0.9638 0.025 Uiso 1 1 calc R . . C7 C 0.99609(19) 0.4387(2) 0.83318(18) 0.0173(5) Uani 1 1 d . . . H7 H 0.9885 0.4906 0.8197 0.021 Uiso 1 1 calc R . . C8 C 0.74183(19) 0.30358(19) 0.71292(18) 0.0156(5) Uani 1 1 d . . . C9 C 0.73989(19) 0.3229(2) 0.80913(19) 0.0193(5) Uani 1 1 d . . . H91 H 0.7924 0.3227 0.8502 0.023 Uiso 1 1 calc R . . C10 C 0.6608(2) 0.3426(2) 0.8447(2) 0.0227(6) Uani 1 1 d . . . H10 H 0.6614 0.3560 0.9093 0.027 Uiso 1 1 calc R . . C11 C 0.5816(2) 0.3422(2) 0.7848(2) 0.0231(6) Uani 1 1 d . . . H11 H 0.5290 0.3558 0.8086 0.028 Uiso 1 1 calc R . . C12 C 0.5813(2) 0.3215(2) 0.6885(2) 0.0234(6) Uani 1 1 d . . . H12 H 0.5278 0.3205 0.6474 0.028 Uiso 1 1 calc R . . C13 C 0.6605(2) 0.3020(2) 0.65283(19) 0.0209(5) Uani 1 1 d . . . H13 H 0.6590 0.2878 0.5879 0.025 Uiso 1 1 calc R . . C14 C 0.78133(19) 0.15401(19) 0.59807(17) 0.0151(5) Uani 1 1 d . . . C15 C 0.6740(2) 0.0716(2) 0.57852(19) 0.0212(5) Uani 1 1 d . . . H15 H 0.6282 0.0934 0.6081 0.025 Uiso 1 1 calc R . . C16 C 0.6340(2) -0.0427(2) 0.5156(2) 0.0280(6) Uani 1 1 d . . . H16 H 0.5622 -0.0968 0.5043 0.034 Uiso 1 1 calc R . . C17 C 0.7000(2) -0.0767(2) 0.4695(2) 0.0262(6) Uani 1 1 d . . . H17 H 0.6733 -0.1534 0.4277 0.031 Uiso 1 1 calc R . . C18 C 0.8062(2) 0.0047(2) 0.48638(19) 0.0227(6) Uani 1 1 d . . . H18 H 0.8509 -0.0171 0.4548 0.027 Uiso 1 1 calc R . . C19 C 0.8465(2) 0.1191(2) 0.55042(19) 0.0197(5) Uani 1 1 d . . . H19 H 0.9182 0.1731 0.5615 0.024 Uiso 1 1 calc R . . C20 C 0.67151(18) 0.22185(19) 0.19455(17) 0.0139(5) Uani 1 1 d . . . C21 C 0.59081(18) 0.23941(19) 0.13774(18) 0.0161(5) Uani 1 1 d . . . C22 C 0.52801(19) 0.2803(2) 0.18434(19) 0.0215(5) Uani 1 1 d . . . H22 H 0.5363 0.2992 0.2512 0.026 Uiso 1 1 calc R . . C23 C 0.4537(2) 0.2934(2) 0.1333(2) 0.0259(6) Uani 1 1 d . . . H23 H 0.4127 0.3207 0.1661 0.031 Uiso 1 1 calc R . . C24 C 0.4398(2) 0.2662(2) 0.0337(2) 0.0250(6) Uani 1 1 d . . . H24 H 0.3906 0.2760 -0.0005 0.030 Uiso 1 1 calc R . . C25 C 0.5005(2) 0.2242(2) -0.01398(19) 0.0224(6) Uani 1 1 d . . . H25 H 0.4909 0.2043 -0.0811 0.027 Uiso 1 1 calc R . . C26 C 0.57573(19) 0.2114(2) 0.03755(18) 0.0184(5) Uani 1 1 d . . . H26 H 0.6164 0.1839 0.0046 0.022 Uiso 1 1 calc R . . C27 C 0.74001(18) 0.1882(2) 0.12975(17) 0.0146(5) Uani 1 1 d . . . C28 C 0.8369(2) 0.2670(2) 0.1279(2) 0.0255(6) Uani 1 1 d . . . H28 H 0.8649 0.3441 0.1689 0.031 Uiso 1 1 calc R . . C29 C 0.8928(2) 0.2322(2) 0.0655(2) 0.0309(7) Uani 1 1 d . . . H29 H 0.9581 0.2864 0.0660 0.037 Uiso 1 1 calc R . . C30 C 0.8524(2) 0.1188(2) 0.0032(2) 0.0251(6) Uani 1 1 d . . . H30 H 0.8896 0.0959 -0.0387 0.030 Uiso 1 1 calc R . . C31 C 0.7558(2) 0.0394(2) 0.0038(2) 0.0231(6) Uani 1 1 d . . . H31 H 0.7274 -0.0377 -0.0383 0.028 Uiso 1 1 calc R . . C32 C 0.7006(2) 0.0737(2) 0.06691(19) 0.0191(5) Uani 1 1 d . . . H32 H 0.6362 0.0192 0.0671 0.023 Uiso 1 1 calc R . . C33 C 0.6123(2) 0.12883(19) 0.22301(18) 0.0172(5) Uani 1 1 d . . . C34 C 0.6765(2) 0.1027(2) 0.27257(19) 0.0221(6) Uani 1 1 d . . . H34 H 0.7530 0.1420 0.2884 0.027 Uiso 1 1 calc R . . C35 C 0.6274(2) 0.0195(2) 0.2978(2) 0.0289(6) Uani 1 1 d . . . H35 H 0.6711 0.0041 0.3316 0.035 Uiso 1 1 calc R . . C36 C 0.5142(3) -0.0409(2) 0.2735(2) 0.0308(7) Uani 1 1 d . . . H36 H 0.4815 -0.0964 0.2914 0.037 Uiso 1 1 calc R . . C37 C 0.4495(2) -0.0193(2) 0.2227(2) 0.0296(7) Uani 1 1 d . . . H37 H 0.3729 -0.0613 0.2051 0.036 Uiso 1 1 calc R . . C38 C 0.4979(2) 0.0657(2) 0.19727(19) 0.0223(6) Uani 1 1 d . . . H38 H 0.4534 0.0799 0.1630 0.027 Uiso 1 1 calc R . . C39 C 0.14511(19) 0.2345(2) 0.31941(17) 0.0146(5) Uani 1 1 d . . . C40 C 0.2609(2) 0.2689(2) 0.37895(19) 0.0181(5) Uani 1 1 d . . . C41 C 0.3225(2) 0.3583(2) 0.4775(2) 0.0234(6) Uani 1 1 d . . . H41 H 0.2917 0.3979 0.5133 0.028 Uiso 1 1 calc R . . C42 C 0.4290(2) 0.3887(2) 0.5226(2) 0.0295(6) Uani 1 1 d . . . H42 H 0.4696 0.4498 0.5877 0.035 Uiso 1 1 calc R . . C43 C 0.4757(2) 0.3299(3) 0.4725(2) 0.0313(7) Uani 1 1 d . . . H43 H 0.5479 0.3517 0.5028 0.038 Uiso 1 1 calc R . . C44 C 0.4147(2) 0.2384(3) 0.3771(2) 0.0315(7) Uani 1 1 d . . . H44 H 0.4447 0.1964 0.3437 0.038 Uiso 1 1 calc R . . C45 C 0.3090(2) 0.2083(3) 0.3302(2) 0.0273(6) Uani 1 1 d . . . H45 H 0.2692 0.1467 0.2652 0.033 Uiso 1 1 calc R . . C46 C 0.15625(18) 0.2451(2) 0.22423(17) 0.0147(5) Uani 1 1 d . . . C47 C 0.2119(2) 0.3512(2) 0.23131(19) 0.0188(5) Uani 1 1 d . . . H47 H 0.2405 0.4166 0.2934 0.023 Uiso 1 1 calc R . . C48 C 0.2251(2) 0.3605(2) 0.14672(19) 0.0206(5) Uani 1 1 d . . . H48 H 0.2597 0.4319 0.1522 0.025 Uiso 1 1 calc R . . C49 C 0.1875(2) 0.2649(2) 0.05453(19) 0.0205(5) Uani 1 1 d . . . H49 H 0.1969 0.2715 -0.0019 0.025 Uiso 1 1 calc R . . C50 C 0.1355(2) 0.1591(2) 0.04719(19) 0.0213(5) Uani 1 1 d . . . H50 H 0.1112 0.0942 -0.0141 0.026 Uiso 1 1 calc R . . C51 C 0.1197(2) 0.1498(2) 0.13142(18) 0.0182(5) Uani 1 1 d . . . H51 H 0.0839 0.0782 0.1254 0.022 Uiso 1 1 calc R . . C52 C 0.0532(2) 0.1143(2) 0.29367(18) 0.0179(5) Uani 1 1 d . . . C53 C -0.0519(2) 0.0610(2) 0.22466(19) 0.0213(5) Uani 1 1 d . . . H53 H -0.0645 0.0957 0.1904 0.026 Uiso 1 1 calc R . . C54 C -0.1376(2) -0.0424(2) 0.20636(19) 0.0238(6) Uani 1 1 d . . . H54 H -0.2071 -0.0761 0.1607 0.029 Uiso 1 1 calc R . . C55 C -0.1199(2) -0.0955(2) 0.2559(2) 0.0274(6) Uani 1 1 d . . . H55 H -0.1770 -0.1652 0.2433 0.033 Uiso 1 1 calc R . . C56 C -0.0168(2) -0.0440(2) 0.3240(2) 0.0282(6) Uani 1 1 d . . . H56 H -0.0046 -0.0794 0.3576 0.034 Uiso 1 1 calc R . . C57 C 0.0692(2) 0.0600(2) 0.3432(2) 0.0225(6) Uani 1 1 d . . . H57 H 0.1382 0.0937 0.3898 0.027 Uiso 1 1 calc R . . C101 C 0.7071(3) 0.5551(3) 0.1802(2) 0.0329(7) Uani 1 1 d . . . H10A H 0.6738 0.4760 0.1626 0.039 Uiso 1 1 calc R A 1 H10B H 0.7846 0.5850 0.1862 0.039 Uiso 1 1 calc R A 1 Cl2 Cl 0.63949(6) 0.56515(7) 0.08466(6) 0.0407(2) Uani 1 1 d . B . Cl1A Cl 0.6961(4) 0.6314(5) 0.2942(4) 0.0472(7) Uani 0.60 1 d P B 1 Cl1B Cl 0.7316(7) 0.6526(8) 0.3046(7) 0.090(3) Uani 0.40 1 d P B 2 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 0.0141(3) 0.0130(3) 0.0114(3) 0.0051(3) 0.0036(2) 0.0055(3) P2 0.0115(3) 0.0115(3) 0.0106(3) 0.0028(2) 0.0022(2) 0.0055(2) P3 0.0167(3) 0.0168(3) 0.0133(3) 0.0048(3) 0.0055(2) 0.0112(3) O1 0.0174(8) 0.0156(8) 0.0135(9) 0.0052(7) 0.0054(7) 0.0065(7) O2 0.0206(9) 0.0197(9) 0.0129(9) 0.0092(8) 0.0031(7) 0.0075(8) O3 0.0249(9) 0.0152(9) 0.0162(9) 0.0074(8) 0.0063(7) 0.0091(8) O4 0.0147(8) 0.0167(8) 0.0127(8) 0.0052(7) 0.0031(7) 0.0079(7) O5 0.0193(8) 0.0110(8) 0.0138(9) 0.0029(7) 0.0017(7) 0.0064(7) O6 0.0145(8) 0.0163(8) 0.0110(8) 0.0000(7) 0.0024(7) 0.0063(7) O7 0.0217(9) 0.0184(9) 0.0137(9) 0.0039(7) 0.0040(7) 0.0124(8) O8 0.0202(9) 0.0221(9) 0.0253(10) 0.0037(8) 0.0047(8) 0.0158(8) O9 0.0356(10) 0.0255(10) 0.0225(10) 0.0121(9) 0.0181(9) 0.0211(9) C1 0.0143(11) 0.0144(12) 0.0129(12) 0.0063(10) 0.0044(10) 0.0063(10) C2 0.0146(11) 0.0178(12) 0.0130(12) 0.0077(10) 0.0074(10) 0.0094(10) C3 0.0218(12) 0.0193(13) 0.0162(13) 0.0077(11) 0.0061(10) 0.0108(11) C4 0.0288(14) 0.0279(14) 0.0185(13) 0.0139(12) 0.0077(11) 0.0181(12) C5 0.0196(13) 0.0313(15) 0.0132(13) 0.0098(12) 0.0020(10) 0.0122(12) C6 0.0181(12) 0.0216(13) 0.0128(12) 0.0043(11) 0.0018(10) 0.0066(11) C7 0.0172(12) 0.0182(12) 0.0141(12) 0.0071(10) 0.0049(10) 0.0085(10) C8 0.0148(11) 0.0102(11) 0.0173(12) 0.0045(10) 0.0067(10) 0.0049(10) C9 0.0149(12) 0.0164(12) 0.0172(13) 0.0051(11) 0.0037(10) 0.0044(10) C10 0.0211(13) 0.0172(13) 0.0202(14) 0.0042(11) 0.0093(11) 0.0067(11) C11 0.0189(12) 0.0163(13) 0.0295(15) 0.0081(12) 0.0125(11) 0.0079(11) C12 0.0192(13) 0.0232(14) 0.0283(15) 0.0128(12) 0.0061(11) 0.0119(11) C13 0.0190(12) 0.0222(13) 0.0184(13) 0.0088(11) 0.0061(10) 0.0094(11) C14 0.0194(12) 0.0142(12) 0.0108(12) 0.0055(10) 0.0035(10) 0.0090(10) C15 0.0206(13) 0.0177(13) 0.0202(13) 0.0067(11) 0.0074(11) 0.0086(11) C16 0.0237(14) 0.0175(13) 0.0313(16) 0.0100(12) 0.0073(12) 0.0042(11) C17 0.0324(15) 0.0128(12) 0.0236(14) 0.0039(11) 0.0024(12) 0.0103(12) C18 0.0314(14) 0.0218(13) 0.0188(13) 0.0076(11) 0.0099(11) 0.0190(12) C19 0.0185(12) 0.0190(13) 0.0186(13) 0.0090(11) 0.0050(10) 0.0081(11) C20 0.0135(11) 0.0100(11) 0.0106(11) 0.0024(10) 0.0029(9) 0.0030(9) C21 0.0100(11) 0.0127(11) 0.0179(13) 0.0054(10) 0.0023(10) 0.0024(9) C22 0.0177(12) 0.0248(14) 0.0153(13) 0.0054(11) 0.0028(10) 0.0108(11) C23 0.0178(13) 0.0301(15) 0.0262(15) 0.0088(13) 0.0044(11) 0.0151(12) C24 0.0190(13) 0.0245(14) 0.0265(15) 0.0118(12) 0.0011(11) 0.0099(11) C25 0.0238(13) 0.0225(13) 0.0160(13) 0.0099(11) 0.0052(11) 0.0082(11) C26 0.0178(12) 0.0156(12) 0.0176(13) 0.0066(11) 0.0063(10) 0.0069(10) C27 0.0139(11) 0.0162(12) 0.0106(12) 0.0049(10) 0.0024(9) 0.0075(10) C28 0.0260(14) 0.0161(13) 0.0245(15) 0.0055(12) 0.0128(12) 0.0067(11) C29 0.0274(15) 0.0261(15) 0.0294(16) 0.0093(13) 0.0178(13) 0.0087(12) C30 0.0250(14) 0.0273(14) 0.0203(14) 0.0057(12) 0.0108(11) 0.0165(12) C31 0.0262(13) 0.0175(13) 0.0208(14) 0.0031(11) 0.0078(11) 0.0137(11) C32 0.0169(12) 0.0156(12) 0.0193(13) 0.0066(11) 0.0051(10) 0.0064(10) C33 0.0207(12) 0.0115(11) 0.0102(12) 0.0014(10) 0.0059(10) 0.0047(10) C34 0.0233(13) 0.0132(12) 0.0160(13) 0.0030(11) 0.0004(11) 0.0041(11) C35 0.0410(16) 0.0193(14) 0.0172(14) 0.0065(12) 0.0060(12) 0.0119(13) C36 0.0491(18) 0.0192(14) 0.0226(15) 0.0109(12) 0.0216(14) 0.0143(13) C37 0.0266(14) 0.0168(13) 0.0301(16) 0.0043(12) 0.0173(13) 0.0046(12) C38 0.0224(13) 0.0186(13) 0.0193(13) 0.0051(11) 0.0099(11) 0.0091(11) C39 0.0180(12) 0.0168(12) 0.0119(12) 0.0063(10) 0.0061(10) 0.0118(10) C40 0.0205(12) 0.0217(13) 0.0190(13) 0.0125(11) 0.0100(11) 0.0135(11) C41 0.0250(13) 0.0248(14) 0.0231(14) 0.0122(12) 0.0080(11) 0.0150(12) C42 0.0270(14) 0.0329(16) 0.0252(15) 0.0152(13) 0.0022(12) 0.0138(13) C43 0.0205(13) 0.0538(19) 0.0364(17) 0.0325(16) 0.0132(13) 0.0223(14) C44 0.0357(16) 0.057(2) 0.0299(16) 0.0272(16) 0.0225(14) 0.0379(16) C45 0.0344(15) 0.0406(17) 0.0203(14) 0.0155(13) 0.0157(12) 0.0282(14) C46 0.0137(11) 0.0185(12) 0.0123(12) 0.0061(10) 0.0045(9) 0.0101(10) C47 0.0209(12) 0.0189(13) 0.0169(13) 0.0062(11) 0.0074(10) 0.0128(11) C48 0.0211(13) 0.0213(13) 0.0256(14) 0.0147(12) 0.0087(11) 0.0127(11) C49 0.0202(12) 0.0327(15) 0.0183(13) 0.0166(12) 0.0094(11) 0.0170(12) C50 0.0182(12) 0.0243(14) 0.0129(12) 0.0021(11) 0.0026(10) 0.0116(11) C51 0.0200(12) 0.0162(12) 0.0186(13) 0.0068(11) 0.0078(10) 0.0111(11) C52 0.0243(13) 0.0170(12) 0.0141(12) 0.0058(10) 0.0107(10) 0.0130(11) C53 0.0256(13) 0.0221(13) 0.0166(13) 0.0074(11) 0.0099(11) 0.0143(11) C54 0.0230(13) 0.0190(13) 0.0169(13) 0.0015(11) 0.0068(11) 0.0080(11) C55 0.0318(15) 0.0173(13) 0.0298(16) 0.0095(12) 0.0168(13) 0.0110(12) C56 0.0399(16) 0.0257(14) 0.0336(16) 0.0194(13) 0.0209(14) 0.0223(13) C57 0.0267(14) 0.0223(13) 0.0223(14) 0.0100(12) 0.0100(11) 0.0163(12) C101 0.0390(17) 0.0368(17) 0.0302(16) 0.0168(14) 0.0151(14) 0.0245(15) Cl2 0.0415(4) 0.0445(5) 0.0420(5) 0.0258(4) 0.0106(4) 0.0237(4) Cl1A 0.0779(15) 0.0580(17) 0.0274(13) 0.0197(12) 0.0312(12) 0.0506(14) Cl1B 0.179(8) 0.078(4) 0.045(3) 0.038(3) 0.036(5) 0.087(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 1.5050(17) . ? P1 O3 1.5450(17) . ? P1 O2 1.5490(17) . ? P1 C1 1.848(2) . ? P2 O4 1.5088(17) . ? P2 O5 1.5464(16) . ? P2 O6 1.5587(16) . ? P2 C20 1.846(2) . ? P3 O7 1.5068(18) . ? P3 O8 1.5419(18) . ? P3 O9 1.5454(18) . ? P3 C39 1.843(2) . ? O2 H2 0.8200 . ? O3 H3 0.8200 . ? O5 H5 0.8200 . ? O6 H6 0.8200 . ? O8 H8 0.8200 . ? O9 H9 0.8200 . ? C1 C2 1.546(3) . ? C1 C14 1.549(3) . ? C1 C8 1.552(3) . ? C2 C7 1.388(3) . ? C2 C3 1.390(3) . ? C3 C4 1.388(3) . ? C3 H92 0.9300 . ? C4 C5 1.382(4) . ? C4 H4 0.9300 . ? C5 C6 1.384(4) . ? C5 H93 0.9300 . ? C6 C7 1.385(3) . ? C6 H61 0.9300 . ? C7 H7 0.9300 . ? C8 C13 1.391(3) . ? C8 C9 1.396(3) . ? C9 C10 1.392(3) . ? C9 H91 0.9300 . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 C12 1.386(4) . ? C11 H11 0.9300 . ? C12 C13 1.392(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.386(3) . ? C14 C19 1.387(3) . ? C15 C16 1.387(4) . ? C15 H15 0.9300 . ? C16 C17 1.381(4) . ? C16 H16 0.9300 . ? C17 C18 1.382(4) . ? C17 H17 0.9300 . ? C18 C19 1.389(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.548(3) . ? C20 C33 1.553(3) . ? C20 C27 1.556(3) . ? C21 C26 1.392(3) . ? C21 C22 1.395(3) . ? C22 C23 1.381(4) . ? C22 H22 0.9300 . ? C23 C24 1.388(4) . ? C23 H23 0.9300 . ? C24 C25 1.383(4) . ? C24 H24 0.9300 . ? C25 C26 1.393(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.387(3) . ? C27 C32 1.390(3) . ? C28 C29 1.394(4) . ? C28 H28 0.9300 . ? C29 C30 1.374(4) . ? C29 H29 0.9300 . ? C30 C31 1.381(4) . ? C30 H30 0.9300 . ? C31 C32 1.390(3) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 C38 1.390(3) . ? C33 C34 1.408(4) . ? C34 C35 1.377(4) . ? C34 H34 0.9300 . ? C35 C36 1.376(4) . ? C35 H35 0.9300 . ? C36 C37 1.372(4) . ? C36 H36 0.9300 . ? C37 C38 1.400(4) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 C40 1.546(3) . ? C39 C52 1.552(3) . ? C39 C46 1.553(3) . ? C40 C41 1.395(4) . ? C40 C45 1.400(3) . ? C41 C42 1.383(4) . ? C41 H41 0.9300 . ? C42 C43 1.374(4) . ? C42 H42 0.9300 . ? C43 C44 1.373(4) . ? C43 H43 0.9300 . ? C44 C45 1.381(4) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 C51 1.387(3) . ? C46 C47 1.392(3) . ? C47 C48 1.388(3) . ? C47 H47 0.9300 . ? C48 C49 1.381(4) . ? C48 H48 0.9300 . ? C49 C50 1.383(4) . ? C49 H49 0.9300 . ? C50 C51 1.390(3) . ? C50 H50 0.9300 . ? C51 H51 0.9300 . ? C52 C57 1.389(3) . ? C52 C53 1.399(3) . ? C53 C54 1.386(4) . ? C53 H53 0.9300 . ? C54 C55 1.383(4) . ? C54 H54 0.9300 . ? C55 C56 1.377(4) . ? C55 H55 0.9300 . ? C56 C57 1.389(4) . ? C56 H56 0.9300 . ? C57 H57 0.9300 . ? C101 Cl1A 1.738(5) . ? C101 Cl1B 1.763(9) . ? C101 Cl2 1.769(3) . ? C101 H10A 0.9700 . ? C101 H10B 0.9700 . ? 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 O3 111.16(9) . . ? O1 P1 O2 112.25(9) . . ? O3 P1 O2 109.70(10) . . ? O1 P1 C1 110.75(10) . . ? O3 P1 C1 106.92(10) . . ? O2 P1 C1 105.80(10) . . ? O4 P2 O5 113.11(9) . . ? O4 P2 O6 108.70(9) . . ? O5 P2 O6 109.34(9) . . ? O4 P2 C20 113.77(10) . . ? O5 P2 C20 105.19(10) . . ? O6 P2 C20 106.46(10) . . ? O7 P3 O8 110.23(10) . . ? O7 P3 O9 112.51(10) . . ? O8 P3 O9 111.80(10) . . ? O7 P3 C39 116.37(10) . . ? O8 P3 C39 103.06(10) . . ? O9 P3 C39 102.34(10) . . ? P1 O2 H2 109.5 . . ? P1 O3 H3 109.5 . . ? P2 O5 H5 109.5 . . ? P2 O6 H6 109.5 . . ? P3 O8 H8 109.5 . . ? P3 O9 H9 109.5 . . ? C2 C1 C14 110.75(19) . . ? C2 C1 C8 108.63(18) . . ? C14 C1 C8 112.10(18) . . ? C2 C1 P1 107.44(15) . . ? C14 C1 P1 107.42(15) . . ? C8 C1 P1 110.40(15) . . ? C7 C2 C3 118.3(2) . . ? C7 C2 C1 120.1(2) . . ? C3 C2 C1 121.3(2) . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H92 119.7 . . ? C2 C3 H92 119.7 . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.4(2) . . ? C4 C5 H93 120.3 . . ? C6 C5 H93 120.3 . . ? C5 C6 C7 120.0(2) . . ? C5 C6 H61 120.0 . . ? C7 C6 H61 120.0 . . ? C6 C7 C2 121.2(2) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? C13 C8 C9 117.8(2) . . ? C13 C8 C1 121.8(2) . . ? C9 C8 C1 120.4(2) . . ? C10 C9 C8 121.2(2) . . ? C10 C9 H91 119.4 . . ? C8 C9 H91 119.4 . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.2(2) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C11 C12 C13 120.6(2) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C8 C13 C12 120.9(2) . . ? C8 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C19 118.1(2) . . ? C15 C14 C1 121.6(2) . . ? C19 C14 C1 120.2(2) . . ? C14 C15 C16 121.0(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 120.4(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.2(2) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 120.2(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C14 C19 C18 121.1(2) . . ? C14 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C21 C20 C33 113.31(18) . . ? C21 C20 C27 110.51(18) . . ? C33 C20 C27 107.95(18) . . ? C21 C20 P2 108.53(15) . . ? C33 C20 P2 106.86(15) . . ? C27 C20 P2 109.58(15) . . ? C26 C21 C22 117.7(2) . . ? C26 C21 C20 121.2(2) . . ? C22 C21 C20 121.1(2) . . ? C23 C22 C21 121.4(2) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 120.5(2) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 118.8(2) . . ? C25 C24 H24 120.6 . . ? C23 C24 H24 120.6 . . ? C24 C25 C26 120.7(2) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C21 C26 C25 120.9(2) . . ? C21 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C28 C27 C32 117.6(2) . . ? C28 C27 C20 123.3(2) . . ? C32 C27 C20 119.0(2) . . ? C27 C28 C29 121.0(2) . . ? C27 C28 H28 119.5 . . ? C29 C28 H28 119.5 . . ? C30 C29 C28 120.7(2) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C29 C30 C31 119.0(2) . . ? C29 C30 H30 120.5 . . ? C31 C30 H30 120.5 . . ? C30 C31 C32 120.5(2) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? C31 C32 C27 121.2(2) . . ? C31 C32 H32 119.4 . . ? C27 C32 H32 119.4 . . ? C38 C33 C34 118.1(2) . . ? C38 C33 C20 123.0(2) . . ? C34 C33 C20 118.8(2) . . ? C35 C34 C33 120.9(2) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C36 C35 C34 120.4(3) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C37 C36 C35 119.9(2) . . ? C37 C36 H36 120.0 . . ? C35 C36 H36 120.0 . . ? C36 C37 C38 120.5(2) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C33 C38 C37 120.2(3) . . ? C33 C38 H38 119.9 . . ? C37 C38 H38 119.9 . . ? C40 C39 C52 112.72(19) . . ? C40 C39 C46 106.26(18) . . ? C52 C39 C46 112.73(19) . . ? C40 C39 P3 112.01(16) . . ? C52 C39 P3 103.43(15) . . ? C46 C39 P3 109.79(15) . . ? C41 C40 C45 117.3(2) . . ? C41 C40 C39 124.6(2) . . ? C45 C40 C39 118.1(2) . . ? C42 C41 C40 120.8(3) . . ? C42 C41 H41 119.6 . . ? C40 C41 H41 119.6 . . ? C43 C42 C41 120.9(3) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C44 C43 C42 119.2(2) . . ? C44 C43 H43 120.4 . . ? C42 C43 H43 120.4 . . ? C43 C44 C45 120.6(3) . . ? C43 C44 H44 119.7 . . ? C45 C44 H44 119.7 . . ? C44 C45 C40 121.1(3) . . ? C44 C45 H45 119.5 . . ? C40 C45 H45 119.5 . . ? C51 C46 C47 117.9(2) . . ? C51 C46 C39 121.0(2) . . ? C47 C46 C39 120.8(2) . . ? C48 C47 C46 120.7(2) . . ? C48 C47 H47 119.7 . . ? C46 C47 H47 119.7 . . ? C49 C48 C47 120.7(2) . . ? C49 C48 H48 119.6 . . ? C47 C48 H48 119.6 . . ? C48 C49 C50 119.1(2) . . ? C48 C49 H49 120.4 . . ? C50 C49 H49 120.4 . . ? C49 C50 C51 120.0(2) . . ? C49 C50 H50 120.0 . . ? C51 C50 H50 120.0 . . ? C46 C51 C50 121.4(2) . . ? C46 C51 H51 119.3 . . ? C50 C51 H51 119.3 . . ? C57 C52 C53 117.9(2) . . ? C57 C52 C39 121.7(2) . . ? C53 C52 C39 120.3(2) . . ? C54 C53 C52 121.2(2) . . ? C54 C53 H53 119.4 . . ? C52 C53 H53 119.4 . . ? C55 C54 C53 120.1(3) . . ? C55 C54 H54 120.0 . . ? C53 C54 H54 120.0 . . ? C56 C55 C54 119.3(2) . . ? C56 C55 H55 120.4 . . ? C54 C55 H55 120.4 . . ? C55 C56 C57 120.9(3) . . ? C55 C56 H56 119.6 . . ? C57 C56 H56 119.6 . . ? C52 C57 C56 120.6(3) . . ? C52 C57 H57 119.7 . . ? C56 C57 H57 119.7 . . ? Cl1A C101 Cl1B 14.1(4) . . ? Cl1A C101 Cl2 109.9(2) . . ? Cl1B C101 Cl2 115.6(3) . . ? Cl1A C101 H10A 109.7 . . ? Cl1B C101 H10A 116.8 . . ? Cl2 C101 H10A 109.7 . . ? Cl1A C101 H10B 109.7 . . ? Cl1B C101 H10B 95.6 . . ? Cl2 C101 H10B 109.7 . . ? H10A C101 H10B 108.2 . . ? 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 O1 P1 C1 C2 40.26(18) . . . . ? O3 P1 C1 C2 -80.98(16) . . . . ? O2 P1 C1 C2 162.13(15) . . . . ? O1 P1 C1 C14 -78.93(17) . . . . ? O3 P1 C1 C14 159.82(15) . . . . ? O2 P1 C1 C14 42.94(17) . . . . ? O1 P1 C1 C8 158.56(15) . . . . ? O3 P1 C1 C8 37.32(18) . . . . ? O2 P1 C1 C8 -79.57(17) . . . . ? C14 C1 C2 C7 167.0(2) . . . . ? C8 C1 C2 C7 -69.5(3) . . . . ? P1 C1 C2 C7 50.0(2) . . . . ? C14 C1 C2 C3 -18.9(3) . . . . ? C8 C1 C2 C3 104.6(2) . . . . ? P1 C1 C2 C3 -135.97(19) . . . . ? C7 C2 C3 C4 0.1(3) . . . . ? C1 C2 C3 C4 -174.0(2) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C7 0.7(4) . . . . ? C5 C6 C7 C2 -0.8(4) . . . . ? C3 C2 C7 C6 0.4(3) . . . . ? C1 C2 C7 C6 174.6(2) . . . . ? C2 C1 C8 C13 163.4(2) . . . . ? C14 C1 C8 C13 -73.9(3) . . . . ? P1 C1 C8 C13 45.8(3) . . . . ? C2 C1 C8 C9 -18.5(3) . . . . ? C14 C1 C8 C9 104.2(2) . . . . ? P1 C1 C8 C9 -136.05(19) . . . . ? C13 C8 C9 C10 -1.4(3) . . . . ? C1 C8 C9 C10 -179.6(2) . . . . ? C8 C9 C10 C11 0.6(4) . . . . ? C9 C10 C11 C12 0.4(4) . . . . ? C10 C11 C12 C13 -0.5(4) . . . . ? C9 C8 C13 C12 1.3(3) . . . . ? C1 C8 C13 C12 179.5(2) . . . . ? C11 C12 C13 C8 -0.3(4) . . . . ? C2 C1 C14 C15 114.2(2) . . . . ? C8 C1 C14 C15 -7.3(3) . . . . ? P1 C1 C14 C15 -128.7(2) . . . . ? C2 C1 C14 C19 -62.9(3) . . . . ? C8 C1 C14 C19 175.6(2) . . . . ? P1 C1 C14 C19 54.2(2) . . . . ? C19 C14 C15 C16 1.9(4) . . . . ? C1 C14 C15 C16 -175.2(2) . . . . ? C14 C15 C16 C17 -1.1(4) . . . . ? C15 C16 C17 C18 -0.5(4) . . . . ? C16 C17 C18 C19 1.2(4) . . . . ? C15 C14 C19 C18 -1.1(4) . . . . ? C1 C14 C19 C18 176.0(2) . . . . ? C17 C18 C19 C14 -0.4(4) . . . . ? O4 P2 C20 C21 -172.36(14) . . . . ? O5 P2 C20 C21 -48.03(16) . . . . ? O6 P2 C20 C21 67.94(16) . . . . ? O4 P2 C20 C33 65.12(17) . . . . ? O5 P2 C20 C33 -170.55(14) . . . . ? O6 P2 C20 C33 -54.58(17) . . . . ? O4 P2 C20 C27 -51.60(18) . . . . ? O5 P2 C20 C27 72.73(17) . . . . ? O6 P2 C20 C27 -171.30(14) . . . . ? C33 C20 C21 C26 -113.1(2) . . . . ? C27 C20 C21 C26 8.2(3) . . . . ? P2 C20 C21 C26 128.4(2) . . . . ? C33 C20 C21 C22 64.8(3) . . . . ? C27 C20 C21 C22 -173.9(2) . . . . ? P2 C20 C21 C22 -53.7(2) . . . . ? C26 C21 C22 C23 -0.3(4) . . . . ? C20 C21 C22 C23 -178.3(2) . . . . ? C21 C22 C23 C24 -0.2(4) . . . . ? C22 C23 C24 C25 0.9(4) . . . . ? C23 C24 C25 C26 -1.2(4) . . . . ? C22 C21 C26 C25 0.1(3) . . . . ? C20 C21 C26 C25 178.0(2) . . . . ? C24 C25 C26 C21 0.7(4) . . . . ? C21 C20 C27 C28 85.1(3) . . . . ? C33 C20 C27 C28 -150.5(2) . . . . ? P2 C20 C27 C28 -34.5(3) . . . . ? C21 C20 C27 C32 -92.0(2) . . . . ? C33 C20 C27 C32 32.4(3) . . . . ? P2 C20 C27 C32 148.46(19) . . . . ? C32 C27 C28 C29 -0.3(4) . . . . ? C20 C27 C28 C29 -177.4(2) . . . . ? C27 C28 C29 C30 0.8(4) . . . . ? C28 C29 C30 C31 -0.4(4) . . . . ? C29 C30 C31 C32 -0.4(4) . . . . ? C30 C31 C32 C27 0.9(4) . . . . ? C28 C27 C32 C31 -0.5(4) . . . . ? C20 C27 C32 C31 176.7(2) . . . . ? C21 C20 C33 C38 1.7(3) . . . . ? C27 C20 C33 C38 -121.0(2) . . . . ? P2 C20 C33 C38 121.2(2) . . . . ? C21 C20 C33 C34 178.3(2) . . . . ? C27 C20 C33 C34 55.6(3) . . . . ? P2 C20 C33 C34 -62.2(2) . . . . ? C38 C33 C34 C35 -2.2(4) . . . . ? C20 C33 C34 C35 -178.9(2) . . . . ? C33 C34 C35 C36 1.1(4) . . . . ? C34 C35 C36 C37 0.7(4) . . . . ? C35 C36 C37 C38 -1.4(4) . . . . ? C34 C33 C38 C37 1.6(4) . . . . ? C20 C33 C38 C37 178.2(2) . . . . ? C36 C37 C38 C33 0.2(4) . . . . ? O7 P3 C39 C40 54.63(19) . . . . ? O8 P3 C39 C40 175.38(16) . . . . ? O9 P3 C39 C40 -68.45(17) . . . . ? O7 P3 C39 C52 176.29(14) . . . . ? O8 P3 C39 C52 -62.96(17) . . . . ? O9 P3 C39 C52 53.21(17) . . . . ? O7 P3 C39 C46 -63.17(18) . . . . ? O8 P3 C39 C46 57.58(17) . . . . ? O9 P3 C39 C46 173.75(15) . . . . ? C52 C39 C40 C41 -115.2(3) . . . . ? C46 C39 C40 C41 120.8(2) . . . . ? P3 C39 C40 C41 0.9(3) . . . . ? C52 C39 C40 C45 66.5(3) . . . . ? C46 C39 C40 C45 -57.5(3) . . . . ? P3 C39 C40 C45 -177.35(19) . . . . ? C45 C40 C41 C42 3.2(4) . . . . ? C39 C40 C41 C42 -175.1(2) . . . . ? C40 C41 C42 C43 -1.7(4) . . . . ? C41 C42 C43 C44 -1.2(4) . . . . ? C42 C43 C44 C45 2.5(4) . . . . ? C43 C44 C45 C40 -0.9(4) . . . . ? C41 C40 C45 C44 -1.9(4) . . . . ? C39 C40 C45 C44 176.5(2) . . . . ? C40 C39 C46 C51 101.2(2) . . . . ? C52 C39 C46 C51 -22.7(3) . . . . ? P3 C39 C46 C51 -137.5(2) . . . . ? C40 C39 C46 C47 -73.1(3) . . . . ? C52 C39 C46 C47 162.9(2) . . . . ? P3 C39 C46 C47 48.2(3) . . . . ? C51 C46 C47 C48 3.2(3) . . . . ? C39 C46 C47 C48 177.7(2) . . . . ? C46 C47 C48 C49 -2.7(4) . . . . ? C47 C48 C49 C50 0.4(4) . . . . ? C48 C49 C50 C51 1.3(4) . . . . ? C47 C46 C51 C50 -1.5(3) . . . . ? C39 C46 C51 C50 -176.0(2) . . . . ? C49 C50 C51 C46 -0.8(4) . . . . ? C40 C39 C52 C57 17.0(3) . . . . ? C46 C39 C52 C57 137.3(2) . . . . ? P3 C39 C52 C57 -104.2(2) . . . . ? C40 C39 C52 C53 -168.0(2) . . . . ? C46 C39 C52 C53 -47.7(3) . . . . ? P3 C39 C52 C53 70.8(2) . . . . ? C57 C52 C53 C54 0.2(4) . . . . ? C39 C52 C53 C54 -175.0(2) . . . . ? C52 C53 C54 C55 -0.7(4) . . . . ? C53 C54 C55 C56 0.6(4) . . . . ? C54 C55 C56 C57 -0.2(4) . . . . ? C53 C52 C57 C56 0.3(4) . . . . ? C39 C52 C57 C56 175.4(2) . . . . ? C55 C56 C57 C52 -0.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O7 0.82 2.06 2.587(2) 122.1 2_666 O3 H3 O8 0.82 2.45 3.121(2) 139.4 2_666 O5 H5 O1 0.82 1.90 2.536(2) 134.0 2_766 O6 H6 O7 0.82 1.86 2.655(2) 164.0 2_666 O8 H8 O4 0.82 1.75 2.537(2) 161.0 1_455 O9 H9 O1 0.82 1.78 2.562(2) 159.8 1_455 O2 H2 O4 0.82 1.85 2.641(2) 160.8 . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.560 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.072 #===END data_1b _database_code_depnum_ccdc_archive 'CCDC 688587' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'phosphonic acid' _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 O3 P1, H2 O' _chemical_formula_sum 'C19 H19 O4 P' _chemical_formula_weight 342.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_HALL '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4867(10) _cell_length_b 11.5664(11) _cell_length_c 14.9036(14) _cell_angle_alpha 74.052(2) _cell_angle_beta 79.399(2) _cell_angle_gamma 89.753(2) _cell_volume 1706.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1874 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.45 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9857 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10420 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7228 _reflns_number_gt 4761 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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. Hydrogen atoms attached to hydroxyl and water molecules were included by the detection of electron density from Fourier map and refined them isotropically completeness has been improved to 0.97 by refining the structure with 2 theta range 2 to 54 ; _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^)+(0.0625P)^2^+1.6538P] 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_number_reflns 7228 _refine_ls_number_parameters 465 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1664 _refine_ls_wR_factor_gt 0.1282 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _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 C1 C 0.1017(3) 0.5053(3) 0.2658(2) 0.0203(6) Uani 1 1 d . . . C2 C 0.2245(3) 0.4812(3) 0.3105(2) 0.0191(6) Uani 1 1 d . . . C3 C 0.2553(3) 0.5514(3) 0.3674(2) 0.0229(7) Uani 1 1 d . . . H3A H 0.2003 0.6139 0.3776 0.027 Uiso 1 1 calc R . . C4 C 0.3634(3) 0.5317(3) 0.4086(2) 0.0291(8) Uani 1 1 d . . . H4 H 0.3807 0.5792 0.4482 0.035 Uiso 1 1 calc R . . C5 C 0.4472(3) 0.4434(3) 0.3930(2) 0.0315(8) Uani 1 1 d . . . H5A H 0.5222 0.4304 0.4212 0.038 Uiso 1 1 calc R . . C6 C 0.4197(3) 0.3744(3) 0.3354(3) 0.0307(8) Uani 1 1 d . . . H6A H 0.4767 0.3140 0.3234 0.037 Uiso 1 1 calc R . . C7 C 0.3096(3) 0.3930(3) 0.2953(2) 0.0261(7) Uani 1 1 d . . . H7 H 0.2919 0.3445 0.2565 0.031 Uiso 1 1 calc R . . C8 C 0.0826(3) 0.4148(3) 0.2094(2) 0.0223(7) Uani 1 1 d . . . C9 C 0.0495(3) 0.2933(3) 0.2560(2) 0.0276(7) Uani 1 1 d . . . H9 H 0.0359 0.2666 0.3234 0.033 Uiso 1 1 calc R . . C10 C 0.0362(4) 0.2113(3) 0.2054(3) 0.0339(8) Uani 1 1 d . . . H10 H 0.0135 0.1292 0.2383 0.041 Uiso 1 1 calc R . . C11 C 0.0561(4) 0.2489(3) 0.1066(3) 0.0329(8) Uani 1 1 d . . . H11 H 0.0478 0.1930 0.0715 0.039 Uiso 1 1 calc R . . C12 C 0.0881(3) 0.3683(3) 0.0605(2) 0.0303(8) Uani 1 1 d . . . H12 H 0.1009 0.3949 -0.0069 0.036 Uiso 1 1 calc R . . C13 C 0.1019(3) 0.4506(3) 0.1108(2) 0.0259(7) Uani 1 1 d . . . H13 H 0.1249 0.5326 0.0774 0.031 Uiso 1 1 calc R . . C14 C 0.1080(3) 0.6362(3) 0.2016(2) 0.0214(7) Uani 1 1 d . . . C15 C 0.2282(3) 0.6957(3) 0.1561(2) 0.0277(7) Uani 1 1 d . . . H15 H 0.3059 0.6568 0.1675 0.033 Uiso 1 1 calc R . . C16 C 0.2352(4) 0.8102(3) 0.0948(2) 0.0342(9) Uani 1 1 d . . . H16 H 0.3175 0.8488 0.0637 0.041 Uiso 1 1 calc R . . C17 C 0.1230(4) 0.8691(3) 0.0782(3) 0.0372(9) Uani 1 1 d . . . H17 H 0.1284 0.9484 0.0368 0.045 Uiso 1 1 calc R . . C18 C 0.0025(4) 0.8117(3) 0.1226(2) 0.0336(8) Uani 1 1 d . . . H18 H -0.0749 0.8518 0.1119 0.040 Uiso 1 1 calc R . . C19 C -0.0040(3) 0.6952(3) 0.1826(2) 0.0263(7) Uani 1 1 d . . . H19 H -0.0865 0.6553 0.2113 0.032 Uiso 1 1 calc R . . C20 C 0.4811(3) -0.0022(3) 0.7322(2) 0.0188(6) Uani 1 1 d . . . C21 C 0.4324(3) 0.0907(3) 0.7865(2) 0.0208(6) Uani 1 1 d . . . C22 C 0.4184(3) 0.2104(3) 0.7387(2) 0.0264(7) Uani 1 1 d . . . H22 H 0.4366 0.2356 0.6712 0.032 Uiso 1 1 calc R . . C23 C 0.3779(3) 0.2935(3) 0.7889(3) 0.0318(8) Uani 1 1 d . . . H23 H 0.3675 0.3745 0.7552 0.038 Uiso 1 1 calc R . . C24 C 0.3530(3) 0.2595(3) 0.8865(3) 0.0330(8) Uani 1 1 d . . . H24 H 0.3259 0.3168 0.9204 0.040 Uiso 1 1 calc R . . C25 C 0.3675(4) 0.1421(3) 0.9348(3) 0.0331(8) Uani 1 1 d . . . H25 H 0.3507 0.1181 1.0023 0.040 Uiso 1 1 calc R . . C26 C 0.4066(3) 0.0581(3) 0.8852(2) 0.0268(7) Uani 1 1 d . . . H26 H 0.4159 -0.0229 0.9195 0.032 Uiso 1 1 calc R . . C27 C 0.4540(3) -0.1318(3) 0.7984(2) 0.0205(6) Uani 1 1 d . . . C28 C 0.3301(3) -0.1876(3) 0.8210(2) 0.0267(7) Uani 1 1 d . . . H28 H 0.2620 -0.1463 0.7936 0.032 Uiso 1 1 calc R . . C29 C 0.3047(4) -0.3030(3) 0.8831(3) 0.0329(8) Uani 1 1 d . . . H29 H 0.2198 -0.3397 0.8979 0.040 Uiso 1 1 calc R . . C30 C 0.4034(4) -0.3641(3) 0.9235(3) 0.0340(8) Uani 1 1 d . . . H30 H 0.3869 -0.4431 0.9653 0.041 Uiso 1 1 calc R . . C31 C 0.5266(4) -0.3086(3) 0.9020(2) 0.0316(8) Uani 1 1 d . . . H31 H 0.5944 -0.3495 0.9301 0.038 Uiso 1 1 calc R . . C32 C 0.5516(3) -0.1945(3) 0.8403(2) 0.0240(7) Uani 1 1 d . . . H32 H 0.6366 -0.1581 0.8262 0.029 Uiso 1 1 calc R . . C33 C 0.6268(3) 0.0205(3) 0.6880(2) 0.0188(6) Uani 1 1 d . . . C34 C 0.7037(3) 0.1090(3) 0.7038(2) 0.0246(7) Uani 1 1 d . . . H34 H 0.6649 0.1587 0.7415 0.029 Uiso 1 1 calc R . . C35 C 0.8354(3) 0.1252(3) 0.6654(3) 0.0304(8) Uani 1 1 d . . . H35 H 0.8861 0.1846 0.6781 0.037 Uiso 1 1 calc R . . C36 C 0.8934(3) 0.0555(3) 0.6087(2) 0.0302(8) Uani 1 1 d . . . H36 H 0.9834 0.0672 0.5819 0.036 Uiso 1 1 calc R . . C37 C 0.8185(3) -0.0315(3) 0.5915(2) 0.0290(8) Uani 1 1 d . . . H37 H 0.8574 -0.0789 0.5520 0.035 Uiso 1 1 calc R . . C38 C 0.6877(3) -0.0500(3) 0.6312(2) 0.0243(7) Uani 1 1 d . . . H38 H 0.6384 -0.1114 0.6197 0.029 Uiso 1 1 calc R . . O1 O -0.0412(2) 0.59703(18) 0.40327(14) 0.0216(5) Uani 1 1 d . . . O2 O -0.1618(2) 0.4651(2) 0.33252(16) 0.0259(5) Uani 1 1 d . . . O3 O -0.0194(2) 0.37137(19) 0.44479(16) 0.0233(5) Uani 1 1 d . . . O4 O 0.4092(2) -0.09849(18) 0.59807(15) 0.0216(5) Uani 1 1 d . . . O5 O 0.4513(2) 0.1283(2) 0.55286(17) 0.0248(5) Uani 1 1 d . . . O6 O 0.2509(2) 0.0357(2) 0.66662(16) 0.0266(5) Uani 1 1 d . . . O1W O 0.1982(3) 0.2336(2) 0.5618(2) 0.0369(6) Uani 1 1 d . . . O2W O -0.2675(3) 0.2657(2) 0.4354(2) 0.0393(7) Uani 1 1 d . . . P1 P -0.03641(8) 0.48849(7) 0.36704(6) 0.0197(2) Uani 1 1 d . . . P2 P 0.39482(8) 0.01233(7) 0.63195(6) 0.0202(2) Uani 1 1 d . . . H1W H 0.169(5) 0.290(4) 0.580(3) 0.057(15) Uiso 1 1 d . . . H5 H 0.481(4) 0.106(4) 0.510(3) 0.056(15) Uiso 1 1 d . . . H6 H 0.216(4) 0.103(4) 0.634(3) 0.058(14) Uiso 1 1 d . . . H3 H 0.001(4) 0.384(4) 0.496(3) 0.049(12) Uiso 1 1 d . . . H2 H -0.213(5) 0.383(5) 0.366(4) 0.081(16) Uiso 1 1 d . . . H2W H 0.262(5) 0.260(4) 0.520(3) 0.048(14) Uiso 1 1 d . . . H3W H -0.314(7) 0.190(6) 0.428(5) 0.14(3) Uiso 1 1 d . . . H4W H -0.211(5) 0.238(5) 0.469(4) 0.079(18) 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 C1 0.0233(17) 0.0186(15) 0.0174(15) -0.0049(12) -0.0002(12) 0.0009(12) C2 0.0173(16) 0.0192(15) 0.0194(15) -0.0039(12) -0.0022(12) 0.0007(12) C3 0.0228(17) 0.0214(16) 0.0235(17) -0.0058(13) -0.0027(13) 0.0018(13) C4 0.0263(19) 0.0335(19) 0.0317(19) -0.0127(15) -0.0107(14) 0.0011(15) C5 0.0249(19) 0.038(2) 0.0321(19) -0.0061(16) -0.0129(15) 0.0038(15) C6 0.0242(18) 0.0240(18) 0.044(2) -0.0090(16) -0.0062(15) 0.0049(14) C7 0.0257(18) 0.0230(17) 0.0315(19) -0.0101(14) -0.0063(14) 0.0009(14) C8 0.0183(16) 0.0278(17) 0.0237(17) -0.0114(14) -0.0047(13) 0.0054(13) C9 0.0280(19) 0.0248(17) 0.0315(19) -0.0095(15) -0.0070(14) 0.0014(14) C10 0.045(2) 0.0242(18) 0.040(2) -0.0154(16) -0.0169(17) 0.0045(16) C11 0.036(2) 0.036(2) 0.038(2) -0.0225(17) -0.0180(16) 0.0125(16) C12 0.034(2) 0.036(2) 0.0288(19) -0.0181(16) -0.0133(15) 0.0126(16) C13 0.0277(18) 0.0266(18) 0.0251(18) -0.0087(14) -0.0068(14) 0.0050(14) C14 0.0279(18) 0.0193(16) 0.0175(15) -0.0052(13) -0.0057(13) 0.0007(13) C15 0.0297(19) 0.0285(18) 0.0246(17) -0.0051(14) -0.0079(14) -0.0006(14) C16 0.043(2) 0.033(2) 0.0203(17) 0.0020(15) -0.0046(15) -0.0120(17) C17 0.055(3) 0.0238(18) 0.030(2) 0.0026(15) -0.0158(18) -0.0052(17) C18 0.048(2) 0.0249(18) 0.0279(19) -0.0014(15) -0.0164(17) 0.0075(16) C19 0.0282(19) 0.0274(18) 0.0240(17) -0.0075(14) -0.0063(14) 0.0000(14) C20 0.0208(16) 0.0172(15) 0.0191(15) -0.0059(12) -0.0045(12) 0.0037(12) C21 0.0192(16) 0.0208(16) 0.0221(16) -0.0070(13) -0.0016(12) 0.0019(12) C22 0.0318(19) 0.0208(16) 0.0260(17) -0.0078(14) -0.0022(14) 0.0018(14) C23 0.034(2) 0.0228(18) 0.040(2) -0.0138(16) -0.0029(16) 0.0040(15) C24 0.032(2) 0.035(2) 0.038(2) -0.0235(17) 0.0003(16) 0.0045(16) C25 0.039(2) 0.036(2) 0.0278(19) -0.0164(16) -0.0015(15) 0.0004(16) C26 0.0316(19) 0.0231(17) 0.0247(17) -0.0073(14) -0.0017(14) 0.0012(14) C27 0.0236(17) 0.0174(15) 0.0198(16) -0.0055(12) -0.0017(12) 0.0027(12) C28 0.0280(18) 0.0250(17) 0.0263(18) -0.0071(14) -0.0033(14) 0.0037(14) C29 0.032(2) 0.0241(18) 0.036(2) -0.0022(15) 0.0023(15) -0.0071(15) C30 0.045(2) 0.0207(17) 0.0294(19) -0.0009(15) -0.0004(16) 0.0042(16) C31 0.040(2) 0.0273(18) 0.0255(18) -0.0035(15) -0.0062(15) 0.0104(16) C32 0.0276(18) 0.0222(17) 0.0211(16) -0.0058(13) -0.0020(13) 0.0023(13) C33 0.0214(16) 0.0188(15) 0.0143(14) -0.0026(12) -0.0016(12) 0.0000(12) C34 0.0266(18) 0.0183(16) 0.0285(18) -0.0070(13) -0.0036(14) 0.0001(13) C35 0.0268(19) 0.0237(17) 0.039(2) -0.0053(15) -0.0071(15) -0.0035(14) C36 0.0171(17) 0.037(2) 0.0322(19) -0.0073(16) 0.0010(14) 0.0005(14) C37 0.0275(19) 0.036(2) 0.0257(18) -0.0137(15) -0.0025(14) 0.0046(15) C38 0.0277(18) 0.0228(17) 0.0242(17) -0.0076(13) -0.0083(14) 0.0015(13) O1 0.0250(12) 0.0191(11) 0.0208(11) -0.0059(9) -0.0039(9) 0.0034(9) O2 0.0219(12) 0.0247(12) 0.0320(13) -0.0070(10) -0.0089(10) 0.0014(10) O3 0.0301(13) 0.0206(12) 0.0181(12) -0.0047(9) -0.0027(10) -0.0010(9) O4 0.0241(12) 0.0165(11) 0.0251(12) -0.0062(9) -0.0067(9) 0.0005(9) O5 0.0327(14) 0.0198(12) 0.0224(13) -0.0060(10) -0.0064(10) 0.0040(10) O6 0.0200(12) 0.0267(13) 0.0321(13) -0.0056(11) -0.0066(10) 0.0059(10) O1W 0.0373(17) 0.0288(15) 0.0407(17) -0.0069(13) -0.0023(13) 0.0112(13) O2W 0.0401(17) 0.0301(15) 0.0476(17) -0.0057(13) -0.0154(14) -0.0097(12) P1 0.0205(4) 0.0183(4) 0.0199(4) -0.0049(3) -0.0034(3) 0.0014(3) P2 0.0218(4) 0.0182(4) 0.0202(4) -0.0047(3) -0.0038(3) 0.0018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.546(4) . ? C1 C8 1.547(4) . ? C1 C14 1.547(4) . ? C1 P1 1.857(3) . ? C2 C7 1.390(4) . ? C2 C3 1.401(4) . ? C3 C4 1.376(4) . ? C3 H3A 0.9500 . ? C4 C5 1.384(5) . ? C4 H4 0.9500 . ? C5 C6 1.389(5) . ? C5 H5A 0.9500 . ? C6 C7 1.385(5) . ? C6 H6A 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.388(4) . ? C8 C9 1.399(4) . ? C9 C10 1.386(4) . ? C9 H9 0.9500 . ? C10 C11 1.393(5) . ? C10 H10 0.9500 . ? C11 C12 1.375(5) . ? C11 H11 0.9500 . ? C12 C13 1.386(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.392(4) . ? C14 C15 1.399(5) . ? C15 C16 1.380(5) . ? C15 H15 0.9500 . ? C16 C17 1.384(5) . ? C16 H16 0.9500 . ? C17 C18 1.391(5) . ? C17 H17 0.9500 . ? C18 C19 1.392(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C33 1.542(4) . ? C20 C27 1.546(4) . ? C20 C21 1.546(4) . ? C20 P2 1.854(3) . ? C21 C26 1.388(4) . ? C21 C22 1.394(4) . ? C22 C23 1.392(4) . ? C22 H22 0.9500 . ? C23 C24 1.374(5) . ? C23 H23 0.9500 . ? C24 C25 1.374(5) . ? C24 H24 0.9500 . ? C25 C26 1.392(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.394(4) . ? C27 C28 1.395(4) . ? C28 C29 1.394(5) . ? C28 H28 0.9500 . ? C29 C30 1.386(5) . ? C29 H29 0.9500 . ? C30 C31 1.388(5) . ? C30 H30 0.9500 . ? C31 C32 1.380(4) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.401(4) . ? C33 C38 1.403(4) . ? C34 C35 1.386(5) . ? C34 H34 0.9500 . ? C35 C36 1.384(5) . ? C35 H35 0.9500 . ? C36 C37 1.385(5) . ? C36 H36 0.9500 . ? C37 C38 1.382(5) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? O1 P1 1.494(2) . ? O2 P1 1.548(2) . ? O2 H2 1.04(5) . ? O3 P1 1.556(2) . ? O3 H3 0.87(4) . ? O4 P2 1.499(2) . ? O5 P2 1.556(2) . ? O5 H5 0.76(4) . ? O6 P2 1.551(2) . ? O6 H6 0.91(5) . ? O1W H1W 0.81(5) . ? O1W H2W 0.82(5) . ? O2W H3W 1.04(8) . ? O2W H4W 0.85(6) . ? P2 H5 1.89(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8 111.7(2) . . ? C2 C1 C14 110.4(2) . . ? C8 C1 C14 110.6(2) . . ? C2 C1 P1 105.7(2) . . ? C8 C1 P1 110.1(2) . . ? C14 C1 P1 108.1(2) . . ? C7 C2 C3 117.3(3) . . ? C7 C2 C1 122.7(3) . . ? C3 C2 C1 119.9(3) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C5 120.8(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 118.8(3) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C6 C7 C2 121.5(3) . . ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 . . ? C13 C8 C9 117.9(3) . . ? C13 C8 C1 121.1(3) . . ? C9 C8 C1 120.9(3) . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.2(3) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 118.9(3) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 121.1(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C8 120.8(3) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C19 C14 C15 118.2(3) . . ? C19 C14 C1 121.5(3) . . ? C15 C14 C1 120.2(3) . . ? C16 C15 C14 120.9(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 120.5(3) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C18 119.7(3) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C19 119.6(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C14 C19 C18 121.2(3) . . ? C14 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C33 C20 C27 110.4(2) . . ? C33 C20 C21 111.5(2) . . ? C27 C20 C21 110.6(2) . . ? C33 C20 P2 106.3(2) . . ? C27 C20 P2 108.1(2) . . ? C21 C20 P2 109.8(2) . . ? C26 C21 C22 117.8(3) . . ? C26 C21 C20 120.7(3) . . ? C22 C21 C20 121.4(3) . . ? C23 C22 C21 120.6(3) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 120.7(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 119.4(3) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 120.4(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 121.1(3) . . ? C21 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C32 C27 C28 118.0(3) . . ? C32 C27 C20 120.9(3) . . ? C28 C27 C20 121.0(3) . . ? C29 C28 C27 121.0(3) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C30 C29 C28 120.0(3) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 119.3(3) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? C32 C31 C30 120.6(3) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C31 C32 C27 121.0(3) . . ? C31 C32 H32 119.5 . . ? C27 C32 H32 119.5 . . ? C34 C33 C38 117.6(3) . . ? C34 C33 C20 122.3(3) . . ? C38 C33 C20 120.2(3) . . ? C35 C34 C33 121.1(3) . . ? C35 C34 H34 119.5 . . ? C33 C34 H34 119.5 . . ? C36 C35 C34 120.4(3) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C37 119.2(3) . . ? C35 C36 H36 120.4 . . ? C37 C36 H36 120.4 . . ? C38 C37 C36 120.8(3) . . ? C38 C37 H37 119.6 . . ? C36 C37 H37 119.6 . . ? C37 C38 C33 120.9(3) . . ? C37 C38 H38 119.5 . . ? C33 C38 H38 119.5 . . ? P1 O2 H2 118(3) . . ? P1 O3 H3 114(3) . . ? P2 O5 H5 104(3) . . ? P2 O6 H6 119(3) . . ? H1W O1W H2W 107(4) . . ? H3W O2W H4W 106(5) . . ? O1 P1 O2 112.97(13) . . ? O1 P1 O3 112.16(12) . . ? O2 P1 O3 105.62(13) . . ? O1 P1 C1 110.42(13) . . ? O2 P1 C1 107.66(14) . . ? O3 P1 C1 107.71(13) . . ? O4 P2 O6 112.55(13) . . ? O4 P2 O5 112.60(13) . . ? O6 P2 O5 105.91(13) . . ? O4 P2 C20 110.08(13) . . ? O6 P2 C20 107.79(13) . . ? O5 P2 C20 107.64(13) . . ? O4 P2 H5 89.6(14) . . ? O6 P2 H5 118.5(14) . . ? O5 P2 H5 23.0(14) . . ? C20 P2 H5 117.0(14) . . ? 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 C8 C1 C2 C7 3.8(4) . . . . ? C14 C1 C2 C7 -119.8(3) . . . . ? P1 C1 C2 C7 123.5(3) . . . . ? C8 C1 C2 C3 -177.6(3) . . . . ? C14 C1 C2 C3 58.8(4) . . . . ? P1 C1 C2 C3 -57.9(3) . . . . ? C7 C2 C3 C4 -1.8(5) . . . . ? C1 C2 C3 C4 179.6(3) . . . . ? C2 C3 C4 C5 1.7(5) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? C5 C6 C7 C2 0.5(5) . . . . ? C3 C2 C7 C6 0.6(5) . . . . ? C1 C2 C7 C6 179.3(3) . . . . ? C2 C1 C8 C13 -109.0(3) . . . . ? C14 C1 C8 C13 14.4(4) . . . . ? P1 C1 C8 C13 133.9(3) . . . . ? C2 C1 C8 C9 68.8(4) . . . . ? C14 C1 C8 C9 -167.7(3) . . . . ? P1 C1 C8 C9 -48.3(3) . . . . ? C13 C8 C9 C10 -0.1(5) . . . . ? C1 C8 C9 C10 -178.0(3) . . . . ? C8 C9 C10 C11 0.2(5) . . . . ? C9 C10 C11 C12 -0.5(5) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C11 C12 C13 C8 -0.6(5) . . . . ? C9 C8 C13 C12 0.3(5) . . . . ? C1 C8 C13 C12 178.2(3) . . . . ? C2 C1 C14 C19 -155.0(3) . . . . ? C8 C1 C14 C19 80.8(3) . . . . ? P1 C1 C14 C19 -39.8(3) . . . . ? C2 C1 C14 C15 28.9(4) . . . . ? C8 C1 C14 C15 -95.2(3) . . . . ? P1 C1 C14 C15 144.1(3) . . . . ? C19 C14 C15 C16 0.5(5) . . . . ? C1 C14 C15 C16 176.7(3) . . . . ? C14 C15 C16 C17 1.0(5) . . . . ? C15 C16 C17 C18 -1.1(5) . . . . ? C16 C17 C18 C19 -0.4(5) . . . . ? C15 C14 C19 C18 -2.0(5) . . . . ? C1 C14 C19 C18 -178.1(3) . . . . ? C17 C18 C19 C14 2.0(5) . . . . ? C33 C20 C21 C26 -105.7(3) . . . . ? C27 C20 C21 C26 17.6(4) . . . . ? P2 C20 C21 C26 136.8(3) . . . . ? C33 C20 C21 C22 71.5(4) . . . . ? C27 C20 C21 C22 -165.2(3) . . . . ? P2 C20 C21 C22 -46.0(4) . . . . ? C26 C21 C22 C23 -0.9(5) . . . . ? C20 C21 C22 C23 -178.2(3) . . . . ? C21 C22 C23 C24 1.0(5) . . . . ? C22 C23 C24 C25 -0.4(5) . . . . ? C23 C24 C25 C26 -0.2(5) . . . . ? C22 C21 C26 C25 0.3(5) . . . . ? C20 C21 C26 C25 177.6(3) . . . . ? C24 C25 C26 C21 0.3(5) . . . . ? C33 C20 C27 C32 24.4(4) . . . . ? C21 C20 C27 C32 -99.4(3) . . . . ? P2 C20 C27 C32 140.4(3) . . . . ? C33 C20 C27 C28 -158.1(3) . . . . ? C21 C20 C27 C28 78.1(3) . . . . ? P2 C20 C27 C28 -42.2(3) . . . . ? C32 C27 C28 C29 -0.4(5) . . . . ? C20 C27 C28 C29 -177.9(3) . . . . ? C27 C28 C29 C30 -0.1(5) . . . . ? C28 C29 C30 C31 0.7(5) . . . . ? C29 C30 C31 C32 -0.9(5) . . . . ? C30 C31 C32 C27 0.4(5) . . . . ? C28 C27 C32 C31 0.2(5) . . . . ? C20 C27 C32 C31 177.8(3) . . . . ? C27 C20 C33 C34 -118.5(3) . . . . ? C21 C20 C33 C34 4.8(4) . . . . ? P2 C20 C33 C34 124.5(3) . . . . ? C27 C20 C33 C38 60.3(4) . . . . ? C21 C20 C33 C38 -176.4(3) . . . . ? P2 C20 C33 C38 -56.7(3) . . . . ? C38 C33 C34 C35 -0.7(5) . . . . ? C20 C33 C34 C35 178.2(3) . . . . ? C33 C34 C35 C36 1.3(5) . . . . ? C34 C35 C36 C37 -0.6(5) . . . . ? C35 C36 C37 C38 -0.8(5) . . . . ? C36 C37 C38 C33 1.5(5) . . . . ? C34 C33 C38 C37 -0.7(5) . . . . ? C20 C33 C38 C37 -179.6(3) . . . . ? C2 C1 P1 O1 76.7(2) . . . . ? C8 C1 P1 O1 -162.54(19) . . . . ? C14 C1 P1 O1 -41.6(2) . . . . ? C2 C1 P1 O2 -159.58(19) . . . . ? C8 C1 P1 O2 -38.8(2) . . . . ? C14 C1 P1 O2 82.1(2) . . . . ? C2 C1 P1 O3 -46.1(2) . . . . ? C8 C1 P1 O3 74.7(2) . . . . ? C14 C1 P1 O3 -164.38(19) . . . . ? C33 C20 P2 O4 76.8(2) . . . . ? C27 C20 P2 O4 -41.8(2) . . . . ? C21 C20 P2 O4 -162.5(2) . . . . ? C33 C20 P2 O6 -160.13(19) . . . . ? C27 C20 P2 O6 81.3(2) . . . . ? C21 C20 P2 O6 -39.4(2) . . . . ? C33 C20 P2 O5 -46.3(2) . . . . ? C27 C20 P2 O5 -164.88(19) . . . . ? C21 C20 P2 O5 74.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W O1 0.81(5) 1.90(5) 2.653(4) 153(5) 2_566 O5 H5 O4 0.76(4) 1.83(5) 2.556(3) 159(5) 2_656 O3 H3 O1 0.87(4) 1.71(4) 2.579(3) 178(4) 2_566 O2W H3W O4 1.04(8) 1.63(8) 2.651(3) 166(6) 2_556 O6 H6 O1W 0.91(5) 1.63(5) 2.515(4) 163(4) . O2 H2 O2W 1.04(5) 1.50(5) 2.521(3) 164(5) . O2W H4W O3 0.85(6) 2.45(5) 2.922(4) 116(4) . _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.612 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.085 #===END data_1c _database_code_depnum_ccdc_archive 'CCDC 688588' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'phosphonic acid' _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 O3 P, C2 H6 O' _chemical_formula_sum 'C21 H23 O4 P' _chemical_formula_weight 370.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_HALL '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7303(10) _cell_length_b 9.7126(11) _cell_length_c 12.1186(14) _cell_angle_alpha 84.159(2) _cell_angle_beta 89.344(2) _cell_angle_gamma 68.104(2) _cell_volume 948.11(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2259 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 28.26 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9328 _exptl_absorpt_correction_T_max 0.9736 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5346 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3644 _reflns_number_gt 3131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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. We did not consider H4a for any hydrogen bonding interactions beacuse of disorder in ethanol molecule. The highest electron density is near to disordered ethanol molecule. The presence of relatively high electron density peaks or holes close to the disordered atoms are common. [P. Muller, R. Herbst-Irmer, A. L. Spek, T. R. Schneider and M. R. Sawaya. Crystal Structure Re?nement. A Crystallographer?s Guide to SHELXL, 2006, chapter 5, pp75.] ; _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^)+(0.0800P)^2^+1.6274P] 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_number_reflns 3644 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1724 _refine_ls_wR_factor_gt 0.1633 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _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 C1 C 0.6362(3) 0.5053(3) 0.2545(2) 0.0147(5) Uani 1 1 d . . . C2 C 0.7740(3) 0.3898(3) 0.3313(2) 0.0146(5) Uani 1 1 d . . . C3 C 0.8551(3) 0.2440(3) 0.3051(2) 0.0180(6) Uani 1 1 d . . . H3' H 0.8249 0.2149 0.2388 0.022 Uiso 1 1 calc R . . C4 C 0.9799(3) 0.1405(3) 0.3749(2) 0.0214(6) Uani 1 1 d . . . H4 H 1.0354 0.0423 0.3549 0.026 Uiso 1 1 calc R . . C5 C 1.0233(3) 0.1799(3) 0.4731(2) 0.0218(6) Uani 1 1 d . . . H5 H 1.1088 0.1095 0.5204 0.026 Uiso 1 1 calc R . . C6 C 0.9404(4) 0.3235(3) 0.5014(2) 0.0212(6) Uani 1 1 d . . . H6 H 0.9678 0.3511 0.5693 0.025 Uiso 1 1 calc R . . C7 C 0.8177(3) 0.4270(3) 0.4311(2) 0.0183(6) Uani 1 1 d . . . H7 H 0.7625 0.5250 0.4515 0.022 Uiso 1 1 calc R . . C8 C 0.6113(3) 0.6650(3) 0.2792(2) 0.0162(6) Uani 1 1 d . . . C9 C 0.7267(4) 0.7275(3) 0.2449(2) 0.0209(6) Uani 1 1 d . . . H9 H 0.8178 0.6730 0.2029 0.025 Uiso 1 1 calc R . . C10 C 0.7105(4) 0.8678(3) 0.2711(3) 0.0288(7) Uani 1 1 d . . . H10 H 0.7891 0.9093 0.2460 0.035 Uiso 1 1 calc R . . C11 C 0.5804(4) 0.9472(3) 0.3337(3) 0.0320(8) Uani 1 1 d . . . H11 H 0.5694 1.0431 0.3522 0.038 Uiso 1 1 calc R . . C12 C 0.4669(4) 0.8864(4) 0.3691(3) 0.0321(8) Uani 1 1 d . . . H12 H 0.3772 0.9413 0.4120 0.039 Uiso 1 1 calc R . . C13 C 0.4811(4) 0.7459(3) 0.3432(2) 0.0224(6) Uani 1 1 d . . . H13 H 0.4023 0.7051 0.3690 0.027 Uiso 1 1 calc R . . C14 C 0.4737(3) 0.4774(3) 0.2667(2) 0.0161(6) Uani 1 1 d . . . C15 C 0.4598(3) 0.3652(3) 0.3421(2) 0.0201(6) Uani 1 1 d . . . H15 H 0.5511 0.3054 0.3897 0.024 Uiso 1 1 calc R . . C16 C 0.3126(4) 0.3401(3) 0.3484(3) 0.0247(6) Uani 1 1 d . . . H16 H 0.3042 0.2636 0.4007 0.030 Uiso 1 1 calc R . . C17 C 0.1787(4) 0.4253(4) 0.2793(3) 0.0269(7) Uani 1 1 d . . . H17 H 0.0797 0.4060 0.2823 0.032 Uiso 1 1 calc R . . C18 C 0.1909(4) 0.5394(4) 0.2056(3) 0.0258(7) Uani 1 1 d . . . H18 H 0.0992 0.5994 0.1584 0.031 Uiso 1 1 calc R . . C19 C 0.3360(3) 0.5665(3) 0.2003(2) 0.0214(6) Uani 1 1 d . . . H19 H 0.3417 0.6468 0.1509 0.026 Uiso 1 1 calc R . . C20 C 1.2202(6) 0.1252(4) 0.1065(4) 0.0509(10) Uani 1 1 d . . . H20A H 1.1403 0.0792 0.1318 0.061 Uiso 0.50 1 calc PR A 1 H20B H 1.2674 0.1483 0.1729 0.061 Uiso 0.50 1 calc PR A 1 H20C H 1.2074 0.1446 0.1854 0.061 Uiso 0.50 1 d PR A 2 H20D H 1.3395 0.0873 0.0909 0.061 Uiso 0.50 1 d PR A 2 C21 C 1.3555(12) 0.0171(11) 0.0468(7) 0.062(3) Uani 0.50 1 d P B 1 H21A H 1.4106 -0.0741 0.0965 0.093 Uiso 0.50 1 calc PR B 1 H21B H 1.4357 0.0617 0.0227 0.093 Uiso 0.50 1 calc PR B 1 H21C H 1.3087 -0.0073 -0.0182 0.093 Uiso 0.50 1 calc PR B 1 C21' C 1.146(2) 0.0066(13) 0.0845(10) 0.112(6) Uani 0.50 1 d P B 2 H21D H 1.2032 -0.0859 0.1326 0.169 Uiso 0.50 1 calc PR B 2 H21E H 1.1605 -0.0134 0.0067 0.169 Uiso 0.50 1 calc PR B 2 H21F H 1.0282 0.0447 0.1006 0.169 Uiso 0.50 1 calc PR B 2 O1 O 0.5941(3) 0.6227(2) 0.03314(16) 0.0228(5) Uani 1 1 d . . . O2 O 0.6708(3) 0.3419(2) 0.07534(16) 0.0217(5) Uani 1 1 d . . . H2 H 0.5710 0.3528 0.0799 0.032 Uiso 1 1 calc R . . O3 O 0.8784(2) 0.4570(2) 0.10257(17) 0.0249(5) Uani 1 1 d . . . H3 H 0.9100 0.4464 0.0372 0.037 Uiso 1 1 calc R . . O4 O 1.1360(3) 0.2607(3) 0.0368(2) 0.0402(6) Uani 1 1 d . B . H4A H 1.0437 0.2624 0.0161 0.060 Uiso 1 1 calc R . . P1 P 0.69270(9) 0.48448(8) 0.10657(6) 0.0165(2) 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 C1 0.0147(13) 0.0182(13) 0.0126(12) -0.0041(10) -0.0002(10) -0.0069(11) C2 0.0125(12) 0.0161(13) 0.0162(13) 0.0013(10) 0.0000(10) -0.0071(10) C3 0.0173(13) 0.0204(14) 0.0167(13) -0.0024(11) -0.0006(11) -0.0073(11) C4 0.0195(14) 0.0172(13) 0.0261(15) -0.0011(11) 0.0025(12) -0.0055(11) C5 0.0165(13) 0.0236(14) 0.0226(14) 0.0074(11) -0.0071(11) -0.0068(11) C6 0.0221(14) 0.0276(15) 0.0164(13) 0.0002(11) -0.0029(11) -0.0126(12) C7 0.0166(13) 0.0209(14) 0.0175(13) -0.0028(11) 0.0006(11) -0.0071(11) C8 0.0167(13) 0.0163(13) 0.0135(12) -0.0011(10) -0.0054(10) -0.0037(11) C9 0.0224(14) 0.0198(14) 0.0208(14) -0.0025(11) -0.0038(11) -0.0078(12) C10 0.0337(17) 0.0215(15) 0.0335(17) -0.0008(13) -0.0091(14) -0.0130(13) C11 0.0372(18) 0.0164(14) 0.0398(19) -0.0070(13) -0.0143(15) -0.0054(13) C12 0.0288(17) 0.0255(16) 0.0339(18) -0.0149(14) -0.0057(14) 0.0025(13) C13 0.0189(14) 0.0226(14) 0.0223(14) -0.0051(12) -0.0034(11) -0.0031(12) C14 0.0138(13) 0.0185(13) 0.0167(13) -0.0075(10) 0.0013(10) -0.0053(11) C15 0.0181(14) 0.0206(14) 0.0224(14) -0.0069(11) 0.0020(11) -0.0069(11) C16 0.0200(14) 0.0254(15) 0.0320(16) -0.0090(13) 0.0071(12) -0.0109(12) C17 0.0178(14) 0.0411(18) 0.0283(16) -0.0151(14) 0.0048(12) -0.0154(13) C18 0.0142(13) 0.0381(17) 0.0227(15) -0.0093(13) -0.0026(11) -0.0055(12) C19 0.0180(14) 0.0271(15) 0.0170(13) -0.0035(11) -0.0018(11) -0.0059(12) C20 0.053(2) 0.038(2) 0.046(2) -0.0001(18) 0.0074(19) -0.0012(19) C21 0.058(6) 0.058(6) 0.041(5) 0.001(4) 0.004(4) 0.010(4) C21' 0.195(16) 0.052(6) 0.052(6) -0.013(5) 0.008(8) -0.002(8) O1 0.0325(11) 0.0199(10) 0.0171(10) 0.0007(8) -0.0066(9) -0.0115(9) O2 0.0257(11) 0.0200(10) 0.0185(10) -0.0041(8) -0.0024(8) -0.0070(8) O3 0.0261(11) 0.0318(12) 0.0194(10) -0.0075(9) 0.0078(8) -0.0128(9) O4 0.0333(13) 0.0389(14) 0.0388(14) -0.0019(11) 0.0046(11) -0.0033(11) P1 0.0200(4) 0.0172(4) 0.0123(3) -0.0024(3) -0.0013(3) -0.0068(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.542(3) . ? C1 C14 1.544(4) . ? C1 C8 1.545(4) . ? C1 P1 1.865(3) . ? C2 C7 1.394(4) . ? C2 C3 1.394(4) . ? C3 C4 1.394(4) . ? C3 H3' 0.9500 . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 C6 1.388(4) . ? C5 H5 0.9500 . ? C6 C7 1.388(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.396(4) . ? C8 C9 1.397(4) . ? C9 C10 1.386(4) . ? C9 H9 0.9500 . ? C10 C11 1.381(5) . ? C10 H10 0.9500 . ? C11 C12 1.375(5) . ? C11 H11 0.9500 . ? C12 C13 1.392(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.390(4) . ? C14 C19 1.395(4) . ? C15 C16 1.395(4) . ? C15 H15 0.9500 . ? C16 C17 1.383(4) . ? C16 H16 0.9500 . ? C17 C18 1.386(5) . ? C17 H17 0.9500 . ? C18 C19 1.386(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 O4 1.433(5) . ? C20 C21 1.494(9) . ? C20 C21' 1.562(16) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 H20C 0.9900 . ? C20 H20D 0.9900 . ? C21 H20D 0.8791 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C21' H21D 0.9800 . ? C21' H21E 0.9800 . ? C21' H21F 0.9800 . ? O1 P1 1.499(2) . ? O2 P1 1.550(2) . ? O2 H2 0.8400 . ? O3 P1 1.542(2) . ? O3 H3 0.8400 . ? O4 H4A 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C14 110.9(2) . . ? C2 C1 C8 110.2(2) . . ? C14 C1 C8 111.1(2) . . ? C2 C1 P1 109.90(17) . . ? C14 C1 P1 105.62(16) . . ? C8 C1 P1 109.04(18) . . ? C7 C2 C3 117.9(2) . . ? C7 C2 C1 120.7(2) . . ? C3 C2 C1 121.4(2) . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3' 119.5 . . ? C4 C3 H3' 119.5 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.1(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C7 120.4(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 121.2(3) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? C13 C8 C9 118.3(3) . . ? C13 C8 C1 121.2(2) . . ? C9 C8 C1 120.3(2) . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 120.1(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 119.5(3) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 121.1(3) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 119.9(3) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? C15 C14 C19 118.5(3) . . ? C15 C14 C1 121.9(2) . . ? C19 C14 C1 119.6(2) . . ? C14 C15 C16 120.4(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 120.7(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.1(3) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C14 120.8(3) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? O4 C20 C21 111.4(5) . . ? O4 C20 C21' 109.4(6) . . ? C21 C20 C21' 77.6(7) . . ? O4 C20 H20A 109.3 . . ? C21 C20 H20A 109.3 . . ? C21' C20 H20A 34.9 . . ? O4 C20 H20B 109.3 . . ? C21 C20 H20B 109.3 . . ? C21' C20 H20B 134.2 . . ? H20A C20 H20B 108.0 . . ? O4 C20 H20C 109.8 . . ? C21 C20 H20C 132.4 . . ? C21' C20 H20C 109.7 . . ? H20A C20 H20C 77.6 . . ? H20B C20 H20C 32.6 . . ? O4 C20 H20D 109.8 . . ? C21 C20 H20D 34.4 . . ? C21' C20 H20D 109.9 . . ? H20A C20 H20D 135.2 . . ? H20B C20 H20D 78.3 . . ? H20C C20 H20D 108.2 . . ? C20 C21 H20D 39.6 . . ? C20 C21 H21A 109.5 . . ? H20D C21 H21A 102.4 . . ? C20 C21 H21B 109.5 . . ? H20D C21 H21B 76.1 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H20D C21 H21C 142.8 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C21' H21D 109.5 . . ? C20 C21' H21E 109.5 . . ? H21D C21' H21E 109.5 . . ? C20 C21' H21F 109.5 . . ? H21D C21' H21F 109.5 . . ? H21E C21' H21F 109.5 . . ? P1 O2 H2 109.5 . . ? P1 O3 H3 109.5 . . ? C20 O4 H4A 109.5 . . ? O1 P1 O3 110.54(12) . . ? O1 P1 O2 113.58(11) . . ? O3 P1 O2 107.77(11) . . ? O1 P1 C1 110.90(12) . . ? O3 P1 C1 105.83(11) . . ? O2 P1 C1 107.86(12) . . ? 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 C14 C1 C2 C7 -101.5(3) . . . . ? C8 C1 C2 C7 21.9(3) . . . . ? P1 C1 C2 C7 142.1(2) . . . . ? C14 C1 C2 C3 76.4(3) . . . . ? C8 C1 C2 C3 -160.2(2) . . . . ? P1 C1 C2 C3 -40.0(3) . . . . ? C7 C2 C3 C4 -2.2(4) . . . . ? C1 C2 C3 C4 179.8(2) . . . . ? C2 C3 C4 C5 1.4(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C7 -1.2(4) . . . . ? C5 C6 C7 C2 0.3(4) . . . . ? C3 C2 C7 C6 1.4(4) . . . . ? C1 C2 C7 C6 179.3(2) . . . . ? C2 C1 C8 C13 -101.0(3) . . . . ? C14 C1 C8 C13 22.3(3) . . . . ? P1 C1 C8 C13 138.3(2) . . . . ? C2 C1 C8 C9 74.0(3) . . . . ? C14 C1 C8 C9 -162.6(2) . . . . ? P1 C1 C8 C9 -46.7(3) . . . . ? C13 C8 C9 C10 -1.6(4) . . . . ? C1 C8 C9 C10 -176.8(2) . . . . ? C8 C9 C10 C11 1.1(4) . . . . ? C9 C10 C11 C12 -0.4(5) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C11 C12 C13 C8 -0.7(5) . . . . ? C9 C8 C13 C12 1.4(4) . . . . ? C1 C8 C13 C12 176.5(3) . . . . ? C2 C1 C14 C15 2.7(3) . . . . ? C8 C1 C14 C15 -120.2(3) . . . . ? P1 C1 C14 C15 121.7(2) . . . . ? C2 C1 C14 C19 -177.2(2) . . . . ? C8 C1 C14 C19 59.9(3) . . . . ? P1 C1 C14 C19 -58.2(3) . . . . ? C19 C14 C15 C16 2.0(4) . . . . ? C1 C14 C15 C16 -177.9(2) . . . . ? C14 C15 C16 C17 0.5(4) . . . . ? C15 C16 C17 C18 -1.8(4) . . . . ? C16 C17 C18 C19 0.8(4) . . . . ? C17 C18 C19 C14 1.7(4) . . . . ? C15 C14 C19 C18 -3.1(4) . . . . ? C1 C14 C19 C18 176.8(2) . . . . ? C2 C1 P1 O1 -160.92(16) . . . . ? C14 C1 P1 O1 79.39(19) . . . . ? C8 C1 P1 O1 -40.0(2) . . . . ? C2 C1 P1 O3 -41.0(2) . . . . ? C14 C1 P1 O3 -160.69(17) . . . . ? C8 C1 P1 O3 79.89(19) . . . . ? C2 C1 P1 O2 74.13(19) . . . . ? C14 C1 P1 O2 -45.6(2) . . . . ? C8 C1 P1 O2 -164.98(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1 0.84 1.93 2.565(3) 131.3 2_665 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.230 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.086