# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Wei Zhang' _publ_contact_author_email WEI2.ZHANG@UMB.EDU _publ_section_title ; Manganese(III)-Mediated Direct Phosphonation of Arylalkenes and Arylalkynes ; loop_ _publ_author_name 'Wei Zhang' 'Xiang-Qiang Pan' 'Guang-Liang Zhang' 'Jian-Ping Zou' # Attachment 'Compound_A.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 743887' #TrackingRef 'Compound_A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 N O4 P' _chemical_formula_sum 'C11 H14 N O4 P' _chemical_formula_weight 255.20 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' N N 0.0061 0.0033 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.732(4) _cell_length_b 9.2832(11) _cell_length_c 18.052(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.924(4) _cell_angle_gamma 90.00 _cell_volume 3985.5(9) _cell_formula_units_Z 12 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11409 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37451 _diffrn_reflns_av_R_equivalents 0.0649 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 25.35 _reflns_number_total 7277 _reflns_number_gt 5067 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of 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^)+(0.0460P)^2^+2.8253P] 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 7277 _refine_ls_number_parameters 466 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.1667 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.170 _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 P1 P 0.49431(5) 0.36683(11) 0.32257(6) 0.0508(3) Uani 1 1 d . . . P2 P 0.08218(4) 0.35293(12) 0.47825(6) 0.0511(3) Uani 1 1 d . . . P3 P 0.09839(5) 0.84863(12) 0.34450(6) 0.0561(3) Uani 1 1 d . . . O1 O 0.45732(11) 0.1618(3) 0.46073(13) 0.0560(7) Uani 1 1 d . . . O2 O 0.47852(11) 0.4373(3) 0.24747(14) 0.0582(7) Uani 1 1 d . . . O3 O 0.49083(17) 0.4634(3) 0.39189(17) 0.0936(12) Uani 1 1 d . . . O4 O 0.55634(12) 0.3141(4) 0.34828(19) 0.0836(10) Uani 1 1 d . . . O5 O 0.13276(12) 0.1934(3) 0.65189(14) 0.0604(7) Uani 1 1 d . . . O6 O 0.09363(12) 0.4262(3) 0.41299(15) 0.0730(9) Uani 1 1 d . . . O7 O 0.02740(11) 0.2599(3) 0.46047(17) 0.0730(8) Uani 1 1 d . . . O8 O 0.06923(13) 0.4518(3) 0.54151(16) 0.0708(8) Uani 1 1 d . . . O9 O 0.03932(12) 0.7815(4) 0.30814(17) 0.0852(10) Uani 1 1 d . . . O10 O 0.14476(12) 0.6767(3) 0.20657(14) 0.0583(7) Uani 1 1 d . . . O11 O 0.10888(13) 0.9053(3) 0.42237(15) 0.0792(9) Uani 1 1 d . . . O12 O 0.09756(14) 0.9640(3) 0.28099(16) 0.0734(9) Uani 1 1 d . . . N1 N 0.49763(13) 0.0087(3) 0.39486(17) 0.0536(8) Uani 1 1 d . . . H1A H 0.5096 -0.0474 0.4338 0.064 Uiso 1 1 calc R . . H1B H 0.5044 -0.0112 0.3518 0.064 Uiso 1 1 calc R . . N2 N 0.12073(14) 0.0053(3) 0.57116(17) 0.0565(9) Uani 1 1 d . . . H2A H 0.1151 -0.0537 0.6050 0.068 Uiso 1 1 calc R . . H2B H 0.1198 -0.0252 0.5258 0.068 Uiso 1 1 calc R . . N3 N 0.11578(14) 0.4993(3) 0.27140(17) 0.0613(9) Uani 1 1 d . . . H3A H 0.1074 0.4431 0.2320 0.074 Uiso 1 1 calc R . . H3B H 0.1107 0.4711 0.3144 0.074 Uiso 1 1 calc R . . C1 C 0.45071(15) 0.2185(4) 0.32981(19) 0.0408(8) Uani 1 1 d . . . C2 C 0.46875(15) 0.1259(4) 0.4012(2) 0.0432(8) Uani 1 1 d . . . C3 C 0.5137(3) 0.6029(5) 0.4052(3) 0.124(2) Uani 1 1 d . . . H3C H 0.5066 0.6418 0.4509 0.186 Uiso 1 1 calc R . . H3D H 0.4965 0.6635 0.3620 0.186 Uiso 1 1 calc R . . H3E H 0.5535 0.5986 0.4117 0.186 Uiso 1 1 calc R . . C4 C 0.5843(2) 0.2640(6) 0.2929(4) 0.107(2) Uani 1 1 d . . . H4A H 0.5734 0.1663 0.2789 0.160 Uiso 1 1 calc R . . H4B H 0.6242 0.2685 0.3149 0.160 Uiso 1 1 calc R . . H4C H 0.5738 0.3237 0.2478 0.160 Uiso 1 1 calc R . . C5 C 0.40431(15) 0.1999(4) 0.2716(2) 0.0477(9) Uani 1 1 d . . . H5 H 0.4002 0.2656 0.2315 0.057 Uiso 1 1 calc R . . C6 C 0.35875(16) 0.0935(4) 0.2602(2) 0.0542(10) Uani 1 1 d . . . C7 C 0.32247(19) 0.0798(5) 0.1868(3) 0.0813(14) Uani 1 1 d . . . H7 H 0.3274 0.1379 0.1472 0.098 Uiso 1 1 calc R . . C8 C 0.2788(2) -0.0193(7) 0.1718(4) 0.0996(18) Uani 1 1 d . . . H8 H 0.2549 -0.0274 0.1223 0.120 Uiso 1 1 calc R . . C9 C 0.2709(2) -0.1040(7) 0.2286(4) 0.0993(18) Uani 1 1 d . . . H9 H 0.2417 -0.1704 0.2183 0.119 Uiso 1 1 calc R . . C10 C 0.3060(2) -0.0917(6) 0.3007(4) 0.1021(19) Uani 1 1 d . . . H10 H 0.3002 -0.1496 0.3399 0.123 Uiso 1 1 calc R . . C11 C 0.35006(19) 0.0051(5) 0.3171(3) 0.0758(14) Uani 1 1 d . . . H11 H 0.3740 0.0107 0.3668 0.091 Uiso 1 1 calc R . . C12 C 0.13898(14) 0.2374(4) 0.52551(18) 0.0411(8) Uani 1 1 d . . . C13 C 0.13073(15) 0.1419(4) 0.58865(19) 0.0423(8) Uani 1 1 d . . . C14 C 0.0085(2) 0.1823(7) 0.3895(4) 0.118(2) Uani 1 1 d . . . H14A H -0.0116 0.2464 0.3497 0.176 Uiso 1 1 calc R . . H14B H -0.0159 0.1054 0.3956 0.176 Uiso 1 1 calc R . . H14C H 0.0403 0.1432 0.3757 0.176 Uiso 1 1 calc R . . C15 C 0.1074(3) 0.5633(6) 0.5755(3) 0.114(2) Uani 1 1 d . . . H15A H 0.1446 0.5242 0.5939 0.171 Uiso 1 1 calc R . . H15B H 0.0963 0.6047 0.6178 0.171 Uiso 1 1 calc R . . H15C H 0.1071 0.6365 0.5378 0.171 Uiso 1 1 calc R . . C16 C 0.18678(15) 0.2442(4) 0.5051(2) 0.0500(9) Uani 1 1 d . . . H16 H 0.1862 0.3087 0.4655 0.060 Uiso 1 1 calc R . . C17 C 0.24022(16) 0.1671(5) 0.5346(2) 0.0552(10) Uani 1 1 d . . . C18 C 0.28011(19) 0.1841(6) 0.4946(3) 0.0863(16) Uani 1 1 d . . . H18 H 0.2721 0.2414 0.4507 0.104 Uiso 1 1 calc R . . C19 C 0.3321(2) 0.1167(8) 0.5195(3) 0.110(2) Uani 1 1 d . . . H19 H 0.3583 0.1282 0.4915 0.132 Uiso 1 1 calc R . . C20 C 0.3451(2) 0.0345(7) 0.5837(4) 0.1030(19) Uani 1 1 d . . . H20 H 0.3798 -0.0113 0.5997 0.124 Uiso 1 1 calc R . . C21 C 0.3065(2) 0.0193(6) 0.6252(3) 0.0970(17) Uani 1 1 d . . . H21 H 0.3152 -0.0367 0.6696 0.116 Uiso 1 1 calc R . . C22 C 0.25548(19) 0.0858(6) 0.6017(3) 0.0801(14) Uani 1 1 d . . . H22 H 0.2303 0.0765 0.6314 0.096 Uiso 1 1 calc R . . C23 C 0.14935(15) 0.7173(4) 0.33764(19) 0.0436(9) Uani 1 1 d . . . C24 C 0.13624(15) 0.6280(4) 0.26595(19) 0.0449(9) Uani 1 1 d . . . C25 C 0.0061(2) 0.7149(7) 0.3513(4) 0.109(2) Uani 1 1 d . . . H25A H 0.0191 0.6180 0.3639 0.163 Uiso 1 1 calc R . . H25B H -0.0325 0.7132 0.3214 0.163 Uiso 1 1 calc R . . H25C H 0.0094 0.7683 0.3979 0.163 Uiso 1 1 calc R . . C26 C 0.1439(3) 1.0621(6) 0.2922(3) 0.111(2) Uani 1 1 d . . . H26A H 0.1460 1.1203 0.3369 0.166 Uiso 1 1 calc R . . H26B H 0.1385 1.1231 0.2478 0.166 Uiso 1 1 calc R . . H26C H 0.1782 1.0088 0.2995 0.166 Uiso 1 1 calc R . . C27 C 0.19770(16) 0.7100(4) 0.3937(2) 0.0525(10) Uani 1 1 d . . . H27 H 0.1993 0.7696 0.4356 0.063 Uiso 1 1 calc R . . C28 C 0.24862(17) 0.6242(5) 0.4003(2) 0.0599(11) Uani 1 1 d . . . C29 C 0.2930(2) 0.6445(7) 0.4653(3) 0.0988(18) Uani 1 1 d . . . H29 H 0.2888 0.7066 0.5038 0.119 Uiso 1 1 calc R . . C30 C 0.3434(3) 0.5731(10) 0.4737(4) 0.147(3) Uani 1 1 d . . . H30 H 0.3729 0.5887 0.5176 0.176 Uiso 1 1 calc R . . C31 C 0.3504(3) 0.4803(9) 0.4186(4) 0.130(3) Uani 1 1 d . . . H31 H 0.3843 0.4318 0.4252 0.155 Uiso 1 1 calc R . . C32 C 0.3080(2) 0.4595(7) 0.3547(3) 0.1019(19) Uani 1 1 d . . . H32 H 0.3128 0.3976 0.3166 0.122 Uiso 1 1 calc R . . C33 C 0.2569(2) 0.5299(5) 0.3452(3) 0.0777(14) Uani 1 1 d . . . H33 H 0.2278 0.5132 0.3009 0.093 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0656(7) 0.0465(6) 0.0405(5) 0.0045(5) 0.0149(5) -0.0078(5) P2 0.0581(6) 0.0552(6) 0.0420(6) 0.0108(5) 0.0174(5) 0.0052(5) P3 0.0701(7) 0.0605(7) 0.0394(6) -0.0073(5) 0.0178(5) 0.0080(6) O1 0.0829(19) 0.0547(16) 0.0377(14) 0.0033(13) 0.0288(13) 0.0116(14) O2 0.0736(18) 0.0565(17) 0.0477(15) 0.0166(13) 0.0218(14) -0.0042(14) O3 0.174(4) 0.0577(19) 0.0582(19) -0.0158(16) 0.048(2) -0.036(2) O4 0.0522(18) 0.093(2) 0.095(2) 0.023(2) 0.0023(17) -0.0134(17) O5 0.102(2) 0.0491(16) 0.0362(14) -0.0016(12) 0.0295(14) 0.0013(15) O6 0.083(2) 0.088(2) 0.0547(17) 0.0343(16) 0.0315(15) 0.0149(17) O7 0.0538(17) 0.088(2) 0.075(2) 0.0048(18) 0.0150(15) -0.0084(16) O8 0.084(2) 0.074(2) 0.0591(18) 0.0001(16) 0.0285(16) 0.0241(18) O9 0.0606(19) 0.127(3) 0.068(2) -0.016(2) 0.0166(16) -0.010(2) O10 0.092(2) 0.0539(16) 0.0344(14) -0.0024(12) 0.0270(13) -0.0120(15) O11 0.109(2) 0.088(2) 0.0452(16) -0.0214(16) 0.0279(16) 0.0176(19) O12 0.099(2) 0.0618(19) 0.0618(19) 0.0089(15) 0.0254(17) 0.0187(18) N1 0.083(2) 0.0437(18) 0.0390(17) 0.0055(14) 0.0256(16) 0.0167(17) N2 0.095(3) 0.0447(19) 0.0344(17) -0.0013(15) 0.0256(17) -0.0108(18) N3 0.099(3) 0.052(2) 0.0397(18) -0.0125(16) 0.0306(18) -0.0205(19) C1 0.057(2) 0.038(2) 0.0342(19) 0.0030(15) 0.0224(17) 0.0037(17) C2 0.054(2) 0.041(2) 0.038(2) 0.0022(17) 0.0188(17) -0.0031(18) C3 0.207(7) 0.063(3) 0.088(4) -0.020(3) 0.015(4) -0.032(4) C4 0.073(3) 0.075(4) 0.174(6) 0.010(4) 0.038(4) 0.013(3) C5 0.057(2) 0.044(2) 0.045(2) 0.0078(18) 0.0189(19) 0.0044(19) C6 0.051(2) 0.052(2) 0.060(3) 0.000(2) 0.015(2) -0.0015(19) C7 0.064(3) 0.087(4) 0.080(3) 0.014(3) -0.002(3) -0.012(3) C8 0.064(3) 0.111(5) 0.106(4) 0.005(4) -0.007(3) -0.020(3) C9 0.071(4) 0.101(4) 0.125(5) -0.009(4) 0.027(4) -0.035(3) C10 0.099(4) 0.112(5) 0.105(4) 0.011(4) 0.044(4) -0.045(4) C11 0.075(3) 0.089(3) 0.068(3) 0.006(3) 0.027(2) -0.025(3) C12 0.049(2) 0.044(2) 0.0325(18) 0.0006(16) 0.0162(16) -0.0010(17) C13 0.052(2) 0.045(2) 0.0335(19) 0.0029(17) 0.0182(16) 0.0056(18) C14 0.086(4) 0.123(5) 0.137(5) -0.062(4) 0.018(4) -0.010(4) C15 0.118(5) 0.096(4) 0.111(5) -0.044(4) 0.003(4) -0.002(4) C16 0.059(2) 0.052(2) 0.041(2) 0.0058(18) 0.0171(18) -0.002(2) C17 0.053(2) 0.066(3) 0.051(2) -0.005(2) 0.0203(19) 0.001(2) C18 0.066(3) 0.129(5) 0.071(3) 0.010(3) 0.031(3) 0.007(3) C19 0.068(4) 0.182(7) 0.093(4) -0.002(4) 0.044(3) 0.018(4) C20 0.071(4) 0.135(5) 0.101(5) -0.004(4) 0.022(3) 0.030(4) C21 0.076(4) 0.118(5) 0.092(4) 0.025(3) 0.015(3) 0.033(3) C22 0.067(3) 0.100(4) 0.075(3) 0.023(3) 0.022(2) 0.026(3) C23 0.058(2) 0.043(2) 0.0311(18) 0.0024(16) 0.0146(17) 0.0006(18) C24 0.056(2) 0.045(2) 0.036(2) -0.0008(17) 0.0155(17) -0.0002(18) C25 0.080(4) 0.119(5) 0.137(5) 0.019(4) 0.046(4) -0.005(4) C26 0.138(5) 0.091(4) 0.114(5) 0.029(4) 0.052(4) 0.003(4) C27 0.070(3) 0.052(2) 0.036(2) 0.0007(18) 0.0156(19) -0.001(2) C28 0.059(3) 0.069(3) 0.050(2) 0.013(2) 0.012(2) 0.001(2) C29 0.075(3) 0.136(5) 0.071(3) -0.005(3) -0.006(3) 0.018(4) C30 0.076(4) 0.226(9) 0.115(6) -0.011(6) -0.013(4) 0.043(5) C31 0.081(4) 0.188(8) 0.119(6) 0.031(5) 0.026(4) 0.054(5) C32 0.091(4) 0.126(5) 0.094(4) 0.022(4) 0.034(3) 0.044(4) C33 0.077(3) 0.092(4) 0.064(3) 0.005(3) 0.020(2) 0.021(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 P1 O2 1.459(2) . ? P1 O4 1.555(3) . ? P1 O3 1.561(3) . ? P1 C1 1.776(4) . ? P2 O6 1.454(3) . ? P2 O7 1.564(3) . ? P2 O8 1.565(3) . ? P2 C12 1.787(4) . ? P3 O11 1.456(3) . ? P3 O9 1.558(3) . ? P3 O12 1.565(3) . ? P3 C23 1.782(4) . ? O1 C2 1.229(4) . ? O3 C3 1.407(5) . ? O4 C4 1.440(6) . ? O5 C13 1.226(4) . ? O7 C14 1.431(6) . ? O8 C15 1.422(6) . ? O9 C25 1.419(5) . ? O10 C24 1.233(4) . ? O12 C26 1.434(6) . ? N1 C2 1.324(4) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C13 1.314(4) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? N3 C24 1.312(4) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? C1 C5 1.337(5) . ? C1 C2 1.511(5) . ? C3 H3C 0.9600 . ? C3 H3D 0.9600 . ? C3 H3E 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.470(5) . ? C5 H5 0.9300 . ? C6 C11 1.378(5) . ? C6 C7 1.387(6) . ? C7 C8 1.387(7) . ? C7 H7 0.9300 . ? C8 C9 1.348(7) . ? C8 H8 0.9300 . ? C9 C10 1.357(7) . ? C9 H9 0.9300 . ? C10 C11 1.381(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C16 1.333(5) . ? C12 C13 1.501(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.468(5) . ? C16 H16 0.9300 . ? C17 C18 1.382(6) . ? C17 C22 1.389(6) . ? C18 C19 1.389(7) . ? C18 H18 0.9300 . ? C19 C20 1.352(7) . ? C19 H19 0.9300 . ? C20 C21 1.371(7) . ? C20 H20 0.9300 . ? C21 C22 1.364(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C27 1.339(5) . ? C23 C24 1.495(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.467(5) . ? C27 H27 0.9300 . ? C28 C29 1.382(6) . ? C28 C33 1.382(6) . ? C29 C30 1.383(8) . ? C29 H29 0.9300 . ? C30 C31 1.363(9) . ? C30 H30 0.9300 . ? C31 C32 1.343(8) . ? C31 H31 0.9300 . ? C32 C33 1.391(6) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? 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 O2 P1 O4 114.15(17) . . ? O2 P1 O3 115.34(17) . . ? O4 P1 O3 102.0(2) . . ? O2 P1 C1 113.77(16) . . ? O4 P1 C1 107.64(17) . . ? O3 P1 C1 102.62(16) . . ? O6 P2 O7 116.26(18) . . ? O6 P2 O8 116.18(18) . . ? O7 P2 O8 97.73(17) . . ? O6 P2 C12 111.43(16) . . ? O7 P2 C12 106.83(17) . . ? O8 P2 C12 107.16(15) . . ? O11 P3 O9 116.70(19) . . ? O11 P3 O12 115.01(18) . . ? O9 P3 O12 98.21(19) . . ? O11 P3 C23 111.86(17) . . ? O9 P3 C23 107.25(18) . . ? O12 P3 C23 106.54(16) . . ? C3 O3 P1 123.9(3) . . ? C4 O4 P1 121.1(3) . . ? C14 O7 P2 120.9(3) . . ? C15 O8 P2 119.8(3) . . ? C25 O9 P3 124.0(3) . . ? C26 O12 P3 118.8(3) . . ? C2 N1 H1A 120.0 . . ? C2 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C13 N2 H2A 120.0 . . ? C13 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C24 N3 H3A 120.0 . . ? C24 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C5 C1 C2 125.9(3) . . ? C5 C1 P1 116.7(3) . . ? C2 C1 P1 117.4(3) . . ? O1 C2 N1 123.9(3) . . ? O1 C2 C1 120.4(3) . . ? N1 C2 C1 115.7(3) . . ? O3 C3 H3C 109.5 . . ? O3 C3 H3D 109.5 . . ? H3C C3 H3D 109.5 . . ? O3 C3 H3E 109.5 . . ? H3C C3 H3E 109.5 . . ? H3D C3 H3E 109.5 . . ? O4 C4 H4A 109.5 . . ? O4 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O4 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C1 C5 C6 131.0(3) . . ? C1 C5 H5 114.5 . . ? C6 C5 H5 114.5 . . ? C11 C6 C7 117.8(4) . . ? C11 C6 C5 124.5(4) . . ? C7 C6 C5 117.8(4) . . ? C6 C7 C8 120.8(5) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 120.4(5) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.5(5) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C11 121.3(5) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C6 C11 C10 120.2(5) . . ? C6 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C16 C12 C13 123.6(3) . . ? C16 C12 P2 118.7(3) . . ? C13 C12 P2 117.6(2) . . ? O5 C13 N2 123.9(3) . . ? O5 C13 C12 119.8(3) . . ? N2 C13 C12 116.3(3) . . ? O7 C14 H14A 109.5 . . ? O7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O8 C15 H15A 109.5 . . ? O8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 C17 130.9(4) . . ? C12 C16 H16 114.5 . . ? C17 C16 H16 114.5 . . ? C18 C17 C22 117.1(4) . . ? C18 C17 C16 117.1(4) . . ? C22 C17 C16 125.7(4) . . ? C17 C18 C19 120.7(5) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.8(5) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 119.3(5) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C22 C21 C20 120.5(5) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C17 121.6(5) . . ? C21 C22 H22 119.2 . . ? C17 C22 H22 119.2 . . ? C27 C23 C24 124.2(3) . . ? C27 C23 P3 119.0(3) . . ? C24 C23 P3 116.7(3) . . ? O10 C24 N3 124.1(3) . . ? O10 C24 C23 120.1(3) . . ? N3 C24 C23 115.9(3) . . ? O9 C25 H25A 109.5 . . ? O9 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O9 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O12 C26 H26A 109.5 . . ? O12 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O12 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 C28 131.1(4) . . ? C23 C27 H27 114.4 . . ? C28 C27 H27 114.4 . . ? C29 C28 C33 117.3(4) . . ? C29 C28 C27 117.3(4) . . ? C33 C28 C27 125.4(4) . . ? C28 C29 C30 120.6(6) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C31 C30 C29 121.0(6) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C32 C31 C30 119.4(6) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? C31 C32 C33 120.6(6) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C28 C33 C32 121.1(5) . . ? C28 C33 H33 119.4 . . ? C32 C33 H33 119.4 . . ? 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 O2 P1 O3 C3 -48.2(5) . . . . ? O4 P1 O3 C3 76.1(5) . . . . ? C1 P1 O3 C3 -172.4(4) . . . . ? O2 P1 O4 C4 -33.0(4) . . . . ? O3 P1 O4 C4 -158.1(4) . . . . ? C1 P1 O4 C4 94.3(4) . . . . ? O6 P2 O7 C14 35.2(4) . . . . ? O8 P2 O7 C14 159.5(4) . . . . ? C12 P2 O7 C14 -89.8(4) . . . . ? O6 P2 O8 C15 -53.4(4) . . . . ? O7 P2 O8 C15 -177.8(4) . . . . ? C12 P2 O8 C15 71.9(4) . . . . ? O11 P3 O9 C25 -29.0(5) . . . . ? O12 P3 O9 C25 -152.5(4) . . . . ? C23 P3 O9 C25 97.3(4) . . . . ? O11 P3 O12 C26 51.6(4) . . . . ? O9 P3 O12 C26 176.2(4) . . . . ? C23 P3 O12 C26 -73.0(4) . . . . ? O2 P1 C1 C5 -9.3(3) . . . . ? O4 P1 C1 C5 -136.9(3) . . . . ? O3 P1 C1 C5 116.0(3) . . . . ? O2 P1 C1 C2 171.4(2) . . . . ? O4 P1 C1 C2 43.9(3) . . . . ? O3 P1 C1 C2 -63.3(3) . . . . ? C5 C1 C2 O1 -95.8(5) . . . . ? P1 C1 C2 O1 83.3(4) . . . . ? C5 C1 C2 N1 85.2(5) . . . . ? P1 C1 C2 N1 -95.6(3) . . . . ? C2 C1 C5 C6 1.5(6) . . . . ? P1 C1 C5 C6 -177.7(3) . . . . ? C1 C5 C6 C11 13.4(7) . . . . ? C1 C5 C6 C7 -165.8(4) . . . . ? C11 C6 C7 C8 0.3(7) . . . . ? C5 C6 C7 C8 179.5(5) . . . . ? C6 C7 C8 C9 0.2(9) . . . . ? C7 C8 C9 C10 0.0(9) . . . . ? C8 C9 C10 C11 -0.6(10) . . . . ? C7 C6 C11 C10 -0.9(7) . . . . ? C5 C6 C11 C10 180.0(4) . . . . ? C9 C10 C11 C6 1.1(9) . . . . ? O6 P2 C12 C16 9.1(4) . . . . ? O7 P2 C12 C16 137.0(3) . . . . ? O8 P2 C12 C16 -119.0(3) . . . . ? O6 P2 C12 C13 -173.4(3) . . . . ? O7 P2 C12 C13 -45.4(3) . . . . ? O8 P2 C12 C13 58.5(3) . . . . ? C16 C12 C13 O5 102.1(4) . . . . ? P2 C12 C13 O5 -75.4(4) . . . . ? C16 C12 C13 N2 -78.9(5) . . . . ? P2 C12 C13 N2 103.7(3) . . . . ? C13 C12 C16 C17 0.7(6) . . . . ? P2 C12 C16 C17 178.1(3) . . . . ? C12 C16 C17 C18 171.9(4) . . . . ? C12 C16 C17 C22 -12.3(7) . . . . ? C22 C17 C18 C19 2.8(8) . . . . ? C16 C17 C18 C19 179.0(5) . . . . ? C17 C18 C19 C20 -0.9(9) . . . . ? C18 C19 C20 C21 -0.8(10) . . . . ? C19 C20 C21 C22 0.3(10) . . . . ? C20 C21 C22 C17 1.8(9) . . . . ? C18 C17 C22 C21 -3.3(8) . . . . ? C16 C17 C22 C21 -179.1(5) . . . . ? O11 P3 C23 C27 -17.0(4) . . . . ? O9 P3 C23 C27 -146.2(3) . . . . ? O12 P3 C23 C27 109.5(3) . . . . ? O11 P3 C23 C24 166.8(3) . . . . ? O9 P3 C23 C24 37.7(3) . . . . ? O12 P3 C23 C24 -66.7(3) . . . . ? C27 C23 C24 O10 -95.0(5) . . . . ? P3 C23 C24 O10 80.9(4) . . . . ? C27 C23 C24 N3 85.0(5) . . . . ? P3 C23 C24 N3 -99.1(4) . . . . ? C24 C23 C27 C28 2.2(6) . . . . ? P3 C23 C27 C28 -173.6(3) . . . . ? C23 C27 C28 C29 177.9(4) . . . . ? C23 C27 C28 C33 1.2(7) . . . . ? C33 C28 C29 C30 0.4(8) . . . . ? C27 C28 C29 C30 -176.6(6) . . . . ? C28 C29 C30 C31 -0.6(12) . . . . ? C29 C30 C31 C32 1.0(13) . . . . ? C30 C31 C32 C33 -1.1(11) . . . . ? C29 C28 C33 C32 -0.6(7) . . . . ? C27 C28 C33 C32 176.1(4) . . . . ? C31 C32 C33 C28 0.9(9) . . . . ? 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 N1 H1A O1 0.86 2.14 2.992(4) 172.4 3_656 N1 H1B O2 0.86 2.01 2.867(4) 178.4 2_645 N2 H2A O10 0.86 2.11 2.896(4) 151.2 4_566 N2 H2B O11 0.86 1.92 2.780(4) 173.7 1_545 N3 H3A O5 0.86 2.14 2.920(4) 150.3 4_565 N3 H3B O6 0.86 1.98 2.839(4) 173.4 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.181 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.052 # Attachment 'Compound_B.cif' data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 743888' #TrackingRef 'Compound_B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 O4 P, H2 O' _chemical_formula_sum 'C17 H17 O5 P' _chemical_formula_weight 332.28 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 monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.723(4) _cell_length_b 7.421(2) _cell_length_c 10.609(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.992(8) _cell_angle_gamma 90.00 _cell_volume 819.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3174 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.3 #_cell_measurement_temperature 293.1 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.728 _exptl_absorpt_correction_T_max 0.910 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7874 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2904 _reflns_number_gt 2501 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? _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^)+(0.0395P)^2^+0.1491P] 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 SHELXL _refine_ls_extinction_coef 0.019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.16(12) _refine_ls_number_reflns 2904 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 P1 P 0.77031(6) 0.33946(11) 0.07678(6) 0.0400(2) Uani 1 1 d . . . O1 O 0.64200(18) 0.2593(3) 0.04007(19) 0.0487(5) Uani 1 1 d . . . O2 O 0.7782(2) 0.5432(3) 0.04466(19) 0.0550(6) Uani 1 1 d . . . O3 O 0.86744(19) 0.2556(3) 0.00446(19) 0.0523(6) Uani 1 1 d . . . O4 O 1.06983(17) 0.3095(4) 0.24931(19) 0.0626(7) Uani 1 1 d . . . O5 O 0.5973(3) 0.8986(5) 0.1212(4) 0.0927(11) Uani 1 1 d . . . H5A H 0.607(4) 1.003(8) 0.102(5) 0.11(2) Uiso 1 1 d . . . H5B H 0.537(4) 0.855(7) 0.068(4) 0.111(17) Uiso 1 1 d . . . C1 C 0.7221(4) 0.6102(5) -0.0842(3) 0.0691(11) Uani 1 1 d . . . H1A H 0.6479 0.5394 -0.1234 0.104 Uiso 1 1 calc R . . H1B H 0.7840 0.6023 -0.1360 0.104 Uiso 1 1 calc R . . H1C H 0.6970 0.7337 -0.0790 0.104 Uiso 1 1 calc R . . C2 C 0.8784(4) 0.0627(5) -0.0040(4) 0.0748(11) Uani 1 1 d . . . H2A H 0.8354 0.0063 0.0551 0.112 Uiso 1 1 calc R . . H2B H 0.9675 0.0292 0.0181 0.112 Uiso 1 1 calc R . . H2C H 0.8395 0.0242 -0.0910 0.112 Uiso 1 1 calc R . . C3 C 0.8428(2) 0.3294(4) 0.2466(2) 0.0377(6) Uani 1 1 d . . . C4 C 0.9843(2) 0.3142(4) 0.3051(3) 0.0433(7) Uani 1 1 d . . . C5 C 0.9993(2) 0.3057(4) 0.4489(2) 0.0429(7) Uani 1 1 d . . . C6 C 1.1071(3) 0.2983(4) 0.5481(3) 0.0518(8) Uani 1 1 d . . . H6 H 1.1882 0.2936 0.5313 0.062 Uiso 1 1 calc R . . C7 C 1.0931(3) 0.2980(5) 0.6752(3) 0.0579(9) Uani 1 1 d . . . H7 H 1.1653 0.2941 0.7444 0.069 Uiso 1 1 calc R . . C8 C 0.9724(3) 0.3034(5) 0.6981(3) 0.0599(9) Uani 1 1 d . . . H8 H 0.9640 0.3006 0.7832 0.072 Uiso 1 1 calc R . . C9 C 0.8619(3) 0.3129(5) 0.5961(3) 0.0528(8) Uani 1 1 d . . . H9 H 0.7806 0.3187 0.6125 0.063 Uiso 1 1 calc R . . C10 C 0.8768(2) 0.3134(4) 0.4713(2) 0.0406(7) Uani 1 1 d . . . C11 C 0.7812(2) 0.3296(4) 0.3438(2) 0.0370(6) Uani 1 1 d . . . C12 C 0.6433(2) 0.3523(5) 0.3366(2) 0.0412(6) Uani 1 1 d . . . C13 C 0.5788(3) 0.5025(4) 0.2738(3) 0.0482(8) Uani 1 1 d . . . H13 H 0.6218 0.5849 0.2334 0.058 Uiso 1 1 calc R . . C14 C 0.4508(3) 0.5283(5) 0.2719(3) 0.0596(9) Uani 1 1 d . . . H14 H 0.4075 0.6283 0.2298 0.072 Uiso 1 1 calc R . . C15 C 0.3873(3) 0.4083(6) 0.3312(3) 0.0656(11) Uani 1 1 d . . . H15 H 0.3011 0.4267 0.3295 0.079 Uiso 1 1 calc R . . C16 C 0.4497(3) 0.2619(6) 0.3928(3) 0.0658(10) Uani 1 1 d . . . H16 H 0.4055 0.1800 0.4322 0.079 Uiso 1 1 calc R . . C17 C 0.5793(3) 0.2331(5) 0.3976(3) 0.0579(9) Uani 1 1 d . . . H17 H 0.6220 0.1341 0.4417 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0450(4) 0.0415(4) 0.0345(3) 0.0002(4) 0.0113(3) -0.0017(4) O1 0.0423(11) 0.0537(12) 0.0477(12) -0.0015(10) 0.0064(9) -0.0064(9) O2 0.0790(15) 0.0398(12) 0.0421(11) 0.0077(9) 0.0067(10) -0.0058(11) O3 0.0580(13) 0.0574(13) 0.0478(12) -0.0038(10) 0.0249(10) 0.0022(10) O4 0.0403(10) 0.096(2) 0.0554(12) -0.0008(14) 0.0192(9) -0.0007(13) O5 0.0691(18) 0.065(2) 0.126(3) 0.0185(18) -0.0115(18) -0.0094(14) C1 0.097(3) 0.062(2) 0.045(2) 0.0185(17) 0.0108(19) -0.0042(19) C2 0.088(3) 0.063(2) 0.079(3) -0.003(2) 0.032(2) 0.019(2) C3 0.0382(13) 0.0396(14) 0.0363(13) 0.0030(15) 0.0107(10) 0.0015(16) C4 0.0390(14) 0.0487(19) 0.0436(14) 0.0032(15) 0.0126(12) 0.0016(15) C5 0.0432(14) 0.043(2) 0.0425(15) 0.0028(14) 0.0103(12) 0.0014(14) C6 0.0423(15) 0.056(2) 0.0543(18) 0.0027(16) 0.0072(13) 0.0053(15) C7 0.0589(19) 0.061(2) 0.0456(17) 0.0031(16) -0.0031(14) 0.0021(17) C8 0.076(2) 0.065(3) 0.0348(15) 0.0024(16) 0.0055(14) -0.0016(19) C9 0.0541(16) 0.067(2) 0.0400(15) 0.0042(17) 0.0155(13) 0.0021(18) C10 0.0396(13) 0.0424(19) 0.0388(14) 0.0070(14) 0.0073(11) 0.0006(14) C11 0.0370(12) 0.0353(14) 0.0394(13) 0.0026(15) 0.0107(10) 0.0007(15) C12 0.0396(13) 0.0517(17) 0.0342(13) -0.0022(15) 0.0129(11) -0.0024(16) C13 0.0417(16) 0.057(2) 0.0468(17) 0.0006(15) 0.0122(13) 0.0025(15) C14 0.0430(17) 0.076(2) 0.058(2) -0.0035(18) 0.0083(15) 0.0158(18) C15 0.0367(16) 0.110(3) 0.050(2) -0.018(2) 0.0107(15) -0.0017(19) C16 0.049(2) 0.098(3) 0.056(2) 0.000(2) 0.0255(16) -0.020(2) C17 0.053(2) 0.070(2) 0.0537(19) 0.0104(17) 0.0194(15) -0.0063(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.463(2) . ? P1 O2 1.557(2) . ? P1 O3 1.564(2) . ? P1 C3 1.783(2) . ? O2 C1 1.443(4) . ? O3 C2 1.440(4) . ? O4 C4 1.206(3) . ? O5 H5A 0.81(6) . ? O5 H5B 0.82(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C11 1.353(3) . ? C3 C4 1.498(3) . ? C4 C5 1.496(4) . ? C5 C6 1.364(4) . ? C5 C10 1.392(4) . ? C6 C7 1.392(4) . ? C6 H6 0.9300 . ? C7 C8 1.374(4) . ? C7 H7 0.9300 . ? C8 C9 1.400(4) . ? C8 H8 0.9300 . ? C9 C10 1.372(4) . ? C9 H9 0.9300 . ? C10 C11 1.491(3) . ? C11 C12 1.471(3) . ? C12 C17 1.373(4) . ? C12 C13 1.393(4) . ? C13 C14 1.382(4) . ? C13 H13 0.9300 . ? C14 C15 1.364(5) . ? C14 H14 0.9300 . ? C15 C16 1.357(5) . ? C15 H15 0.9300 . ? C16 C17 1.395(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? 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 O2 115.72(12) . . ? O1 P1 O3 113.73(13) . . ? O2 P1 O3 101.62(13) . . ? O1 P1 C3 113.85(12) . . ? O2 P1 C3 103.20(13) . . ? O3 P1 C3 107.44(12) . . ? C1 O2 P1 120.7(2) . . ? C2 O3 P1 120.0(2) . . ? H5A O5 H5B 109(5) . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O3 C2 H2A 109.5 . . ? O3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? O3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C11 C3 C4 108.4(2) . . ? C11 C3 P1 126.64(18) . . ? C4 C3 P1 124.90(18) . . ? O4 C4 C5 126.3(2) . . ? O4 C4 C3 127.8(2) . . ? C5 C4 C3 105.9(2) . . ? C6 C5 C10 121.9(2) . . ? C6 C5 C4 130.6(3) . . ? C10 C5 C4 107.4(2) . . ? C5 C6 C7 118.5(3) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C8 C7 C6 119.9(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 121.5(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 118.1(3) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? C9 C10 C5 120.0(2) . . ? C9 C10 C11 131.4(2) . . ? C5 C10 C11 108.6(2) . . ? C3 C11 C12 129.1(2) . . ? C3 C11 C10 109.6(2) . . ? C12 C11 C10 121.2(2) . . ? C17 C12 C13 119.6(3) . . ? C17 C12 C11 120.8(3) . . ? C13 C12 C11 119.5(3) . . ? C14 C13 C12 119.6(3) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.7(3) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 119.4(3) . . ? C12 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? 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 O2 C1 -51.4(3) . . . . ? O3 P1 O2 C1 72.3(3) . . . . ? C3 P1 O2 C1 -176.4(2) . . . . ? O1 P1 O3 C2 -47.4(3) . . . . ? O2 P1 O3 C2 -172.5(2) . . . . ? C3 P1 O3 C2 79.5(3) . . . . ? O1 P1 C3 C11 -29.5(3) . . . . ? O2 P1 C3 C11 96.8(3) . . . . ? O3 P1 C3 C11 -156.4(3) . . . . ? O1 P1 C3 C4 148.8(3) . . . . ? O2 P1 C3 C4 -85.0(3) . . . . ? O3 P1 C3 C4 21.9(3) . . . . ? C11 C3 C4 O4 179.9(4) . . . . ? P1 C3 C4 O4 1.4(5) . . . . ? C11 C3 C4 C5 -0.1(3) . . . . ? P1 C3 C4 C5 -178.6(2) . . . . ? O4 C4 C5 C6 2.8(6) . . . . ? C3 C4 C5 C6 -177.2(3) . . . . ? O4 C4 C5 C10 -179.4(3) . . . . ? C3 C4 C5 C10 0.6(3) . . . . ? C10 C5 C6 C7 0.2(5) . . . . ? C4 C5 C6 C7 177.7(3) . . . . ? C5 C6 C7 C8 0.6(5) . . . . ? C6 C7 C8 C9 -1.3(5) . . . . ? C7 C8 C9 C10 1.2(5) . . . . ? C8 C9 C10 C5 -0.4(5) . . . . ? C8 C9 C10 C11 -177.1(3) . . . . ? C6 C5 C10 C9 -0.2(5) . . . . ? C4 C5 C10 C9 -178.3(3) . . . . ? C6 C5 C10 C11 177.2(3) . . . . ? C4 C5 C10 C11 -0.9(3) . . . . ? C4 C3 C11 C12 176.2(3) . . . . ? P1 C3 C11 C12 -5.4(5) . . . . ? C4 C3 C11 C10 -0.4(3) . . . . ? P1 C3 C11 C10 178.1(2) . . . . ? C9 C10 C11 C3 177.8(3) . . . . ? C5 C10 C11 C3 0.8(4) . . . . ? C9 C10 C11 C12 1.0(6) . . . . ? C5 C10 C11 C12 -176.0(3) . . . . ? C3 C11 C12 C17 129.9(4) . . . . ? C10 C11 C12 C17 -53.9(4) . . . . ? C3 C11 C12 C13 -54.0(5) . . . . ? C10 C11 C12 C13 122.1(3) . . . . ? C17 C12 C13 C14 -1.0(4) . . . . ? C11 C12 C13 C14 -177.1(3) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C13 C14 C15 C16 0.0(5) . . . . ? C14 C15 C16 C17 0.7(5) . . . . ? C13 C12 C17 C16 1.7(4) . . . . ? C11 C12 C17 C16 177.7(3) . . . . ? C15 C16 C17 C12 -1.5(5) . . . . ? 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 O5 H5A O1 0.81(6) 2.08(6) 2.887(4) 174(5) 1_565 O5 H5B O1 0.82(5) 2.11(5) 2.908(4) 167(4) 2_655 C15 H15 O4 0.93 2.57 3.384(4) 146.2 1_455 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.165 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.035