# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Sullivan, A.' 'Gardner, S.' 'Motevalli, M.' 'Shastri, K.' 'Wyatt, P.B.' _publ_contact_author_name 'Prof A Sullivan' _publ_contact_author_address ; Department of Chemistry Queen Mary & Westfield College Mile End Road London E1 4NS UK ; _publ_contact_author_email 'A.C.SULLIVAN@QMUL.AC.UK' _publ_section_title ; Towards enantiomerically pure 1-phenyl-2-carboxyethylphosphonic acid and its esters: structural and synthetic chemistry ; data_asc0021 _database_code_CSD 177846 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H24 N O6 P' _chemical_formula_weight 369.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3857(2) _cell_length_b 25.4539(10) _cell_length_c 9.5109(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.872(3) _cell_angle_gamma 90.00 _cell_volume 1783.92(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9889 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7503 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.1440 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 26.03 _reflns_number_total 5690 _reflns_number_gt 3504 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.21(19) _refine_ls_number_reflns 5690 _refine_ls_number_parameters 472 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1234 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1166 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.973 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 -0.0106(3) -0.07297(8) 0.4350(2) 0.0196(5) Uani 1 1 d . . . P2 P 0.0048(3) 0.00304(8) 0.06397(18) 0.0178(5) Uani 1 1 d . . . O1 O -0.5436(7) -0.1010(2) 0.4493(5) 0.0243(15) Uani 1 1 d . . . H1 H -0.6377 -0.0865 0.4133 0.036 Uiso 1 1 calc R . . O2 O -0.4720(7) -0.1067(2) 0.2224(5) 0.0263(14) Uani 1 1 d . . . O3 O 0.0115(7) -0.0812(2) 0.5897(4) 0.0234(14) Uani 1 1 d . . . O4 O 0.1600(6) -0.0569(2) 0.3643(5) 0.0207(14) Uani 1 1 d . . . O5 O -0.1656(6) -0.0308(2) 0.4046(5) 0.0202(13) Uani 1 1 d . . . H5 H -0.1988 -0.0311 0.3183 0.030 Uiso 1 1 calc R . . O6 O 0.4595(7) 0.0320(2) 0.2670(5) 0.0240(14) Uani 1 1 d . . . O7 O 0.5334(7) 0.0306(2) 0.0439(5) 0.0256(15) Uani 1 1 d . . . H7 H 0.6303 0.0176 0.0799 0.038 Uiso 1 1 calc R . . O8 O -0.0161(6) 0.0131(2) -0.0914(4) 0.0183(13) Uani 1 1 d . . . O9 O -0.1651(6) -0.0128(2) 0.1320(5) 0.0198(14) Uani 1 1 d . . . O10 O 0.1580(7) -0.0394(2) 0.0937(5) 0.0211(13) Uani 1 1 d . . . H10 H 0.1514 -0.0516 0.1752 0.032 Uiso 1 1 calc R . . O11 O -0.2512(7) -0.0488(2) -0.2441(5) 0.0266(15) Uani 1 1 d DU . . O12 O -0.7516(7) -0.0175(2) -0.2593(5) 0.0221(14) Uani 1 1 d DU . . N1 N -0.5246(8) -0.0851(3) -0.0818(6) 0.0243(18) Uani 1 1 d . . . H1A H -0.6021 -0.0579 -0.1020 0.036 Uiso 1 1 calc R . . H1B H -0.4106 -0.0758 -0.1028 0.036 Uiso 1 1 calc R . . H1C H -0.5246 -0.0931 0.0115 0.036 Uiso 1 1 calc R . . N2 N 0.5145(8) 0.0159(3) 0.5667(5) 0.0213(17) Uani 1 1 d . . . H2A H 0.4276 0.0127 0.6295 0.032 Uiso 1 1 calc R . . H2B H 0.6086 -0.0060 0.5915 0.032 Uiso 1 1 calc R . . H2C H 0.4667 0.0074 0.4790 0.032 Uiso 1 1 calc R . . C1 C -0.7638(11) -0.1516(4) -0.1213(8) 0.032(2) Uani 1 1 d . . . H1A' H -0.8101 -0.1794 -0.1850 0.048 Uiso 1 1 calc R . . H1B' H -0.8508 -0.1224 -0.1236 0.048 Uiso 1 1 calc R . . H1C' H -0.7471 -0.1654 -0.0251 0.048 Uiso 1 1 calc R . . C2 C -0.5846(8) -0.1322(2) -0.1676(6) 0.0270(15) Uani 1 1 d . . . H2 H -0.6039 -0.1206 -0.2681 0.032 Uiso 1 1 calc R . . C3 C -0.4399(11) -0.1744(3) -0.1608(8) 0.026(2) Uani 1 1 d . . . C4 C -0.4282(12) -0.2047(4) -0.2795(8) 0.028(2) Uani 1 1 d . . . H4 H -0.5062 -0.1976 -0.3608 0.034 Uiso 1 1 calc R . . C5 C -0.3062(12) -0.2450(4) -0.2822(9) 0.034(2) Uani 1 1 d . . . H5' H -0.3007 -0.2661 -0.3641 0.041 Uiso 1 1 calc R . . C6 C -0.1892(12) -0.2548(4) -0.1629(9) 0.035(2) Uani 1 1 d . . . H6 H -0.1023 -0.2823 -0.1635 0.042 Uiso 1 1 calc R . . C7 C -0.2012(11) -0.2251(4) -0.0485(9) 0.029(2) Uani 1 1 d . . . H7' H -0.1232 -0.2325 0.0326 0.035 Uiso 1 1 calc R . . C8 C -0.3221(11) -0.1842(3) -0.0434(8) 0.030(2) Uani 1 1 d . . . H8 H -0.3251 -0.1630 0.0387 0.036 Uiso 1 1 calc R . . C9 C -0.4406(10) -0.1163(3) 0.3482(8) 0.021(2) Uani 1 1 d . . . C10 C -0.2770(11) -0.1484(3) 0.4058(7) 0.023(2) Uani 1 1 d . . . H10A H -0.2660 -0.1447 0.5096 0.028 Uiso 1 1 calc R . . H10B H -0.3002 -0.1859 0.3838 0.028 Uiso 1 1 calc R . . C11 C -0.0966(11) -0.1328(3) 0.3483(7) 0.018(2) Uani 1 1 d . . . H11 H -0.1176 -0.1256 0.2451 0.021 Uiso 1 1 calc R . . C12 C 0.0432(11) -0.1753(3) 0.3686(8) 0.023(2) Uani 1 1 d . . . C13 C 0.0622(12) -0.2059(4) 0.4882(9) 0.026(2) Uani 1 1 d . . . H13 H -0.0159 -0.2003 0.5622 0.032 Uiso 1 1 calc R . . C14 C 0.1932(11) -0.2447(4) 0.5023(9) 0.027(2) Uani 1 1 d . . . H14 H 0.2037 -0.2655 0.5853 0.032 Uiso 1 1 calc R . . C15 C 0.3097(12) -0.2533(4) 0.3959(9) 0.033(2) Uani 1 1 d . . . H15 H 0.3994 -0.2800 0.4067 0.039 Uiso 1 1 calc R . . C16 C 0.2963(12) -0.2238(4) 0.2761(9) 0.031(2) Uani 1 1 d . . . H16 H 0.3754 -0.2298 0.2030 0.038 Uiso 1 1 calc R . . C17 C 0.1636(11) -0.1843(4) 0.2627(8) 0.025(2) Uani 1 1 d . . . H17 H 0.1548 -0.1632 0.1802 0.030 Uiso 1 1 calc R . . C18 C 0.7630(11) 0.0761(3) 0.6521(8) 0.030(2) Uani 1 1 d . . . H18A H 0.7998 0.1131 0.6596 0.044 Uiso 1 1 calc R . . H18B H 0.8550 0.0562 0.6051 0.044 Uiso 1 1 calc R . . H18C H 0.7509 0.0618 0.7466 0.044 Uiso 1 1 calc R . . C19 C 0.5820(7) 0.0721(2) 0.5666(6) 0.0229(14) Uani 1 1 d . . . H19 H 0.6040 0.0813 0.4670 0.027 Uiso 1 1 calc R . . C20 C 0.4382(10) 0.1084(3) 0.6127(8) 0.0233(19) Uani 1 1 d . . . C21 C 0.4375(11) 0.1294(4) 0.7482(7) 0.027(2) Uani 1 1 d . . . H21 H 0.5278 0.1187 0.8182 0.033 Uiso 1 1 calc R . . C22 C 0.3096(11) 0.1650(4) 0.7820(8) 0.033(2) Uani 1 1 d . . . H22 H 0.3134 0.1790 0.8748 0.040 Uiso 1 1 calc R . . C23 C 0.1747(12) 0.1812(4) 0.6842(8) 0.025(2) Uani 1 1 d . . . H23 H 0.0876 0.2064 0.7094 0.030 Uiso 1 1 calc R . . C24 C 0.1663(11) 0.1603(4) 0.5469(9) 0.030(2) Uani 1 1 d . . . H24 H 0.0718 0.1700 0.4791 0.036 Uiso 1 1 calc R . . C25 C 0.3008(11) 0.1250(3) 0.5134(7) 0.030(2) Uani 1 1 d . . . H25 H 0.2996 0.1117 0.4200 0.036 Uiso 1 1 calc R . . C26 C 0.4279(11) 0.0437(3) 0.1445(8) 0.019(2) Uani 1 1 d . . . C27 C 0.2758(10) 0.0781(3) 0.0926(8) 0.023(2) Uani 1 1 d . . . H27A H 0.2636 0.0766 -0.0116 0.028 Uiso 1 1 calc R . . H27B H 0.3041 0.1148 0.1203 0.028 Uiso 1 1 calc R . . C28 C 0.0927(10) 0.0620(3) 0.1512(8) 0.020(2) Uani 1 1 d . . . H28 H 0.1157 0.0540 0.2538 0.024 Uiso 1 1 calc R . . C29 C -0.0495(10) 0.1053(3) 0.1362(7) 0.0159(19) Uani 1 1 d . . . C30 C -0.0757(11) 0.1340(4) 0.0106(8) 0.023(2) Uani 1 1 d . . . H30 H -0.0017 0.1272 -0.0653 0.027 Uiso 1 1 calc R . . C31 C -0.2103(11) 0.1727(4) -0.0034(9) 0.030(2) Uani 1 1 d . . . H31 H -0.2256 0.1923 -0.0883 0.036 Uiso 1 1 calc R . . C32 C -0.3205(11) 0.1825(4) 0.1038(9) 0.028(2) Uani 1 1 d . . . H32 H -0.4120 0.2088 0.0946 0.034 Uiso 1 1 calc R . . C33 C -0.2942(11) 0.1527(4) 0.2279(8) 0.028(2) Uani 1 1 d . . . H33 H -0.3706 0.1587 0.3028 0.034 Uiso 1 1 calc R . . C34 C -0.1621(11) 0.1156(3) 0.2431(8) 0.022(2) Uani 1 1 d . . . H34 H -0.1469 0.0965 0.3288 0.026 Uiso 1 1 calc R . . H0W1 H -0.167(8) -0.063(2) -0.311(6) 0.078(11) Uiso 1 1 d D . . H0W2 H -0.176(9) -0.029(3) -0.178(6) 0.078(11) Uiso 1 1 d D . . H0W3 H -0.822(9) 0.005(2) -0.219(7) 0.078(11) Uiso 1 1 d D . . H0W4 H -0.822(10) -0.041(3) -0.297(8) 0.078(11) 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 P1 0.0172(13) 0.0216(15) 0.0202(11) -0.0002(11) 0.0020(9) 0.0004(10) P2 0.0188(13) 0.0179(14) 0.0169(11) 0.0022(10) 0.0018(9) 0.0033(10) O1 0.019(3) 0.036(4) 0.017(3) -0.002(3) -0.003(2) 0.004(3) O2 0.025(3) 0.032(4) 0.021(3) 0.003(3) 0.001(2) -0.006(3) O3 0.022(4) 0.028(4) 0.020(3) 0.003(3) 0.003(2) 0.005(3) O4 0.012(3) 0.028(4) 0.023(3) 0.004(3) 0.005(2) 0.001(3) O5 0.017(3) 0.028(4) 0.016(3) 0.000(3) -0.001(2) 0.005(3) O6 0.021(3) 0.033(4) 0.018(3) -0.001(3) -0.001(2) 0.003(3) O7 0.013(3) 0.040(4) 0.024(3) 0.000(3) 0.002(2) 0.007(3) O8 0.015(3) 0.021(4) 0.019(3) -0.001(3) -0.003(2) 0.000(2) O9 0.019(3) 0.021(4) 0.019(3) 0.004(3) 0.004(2) -0.001(3) O10 0.027(3) 0.015(3) 0.022(3) 0.006(3) 0.006(2) 0.003(3) O11 0.032(4) 0.027(4) 0.021(3) -0.004(3) 0.002(2) 0.000(3) O12 0.017(3) 0.024(4) 0.025(3) -0.005(3) 0.003(2) -0.001(3) N1 0.022(4) 0.026(5) 0.025(3) 0.004(3) 0.008(3) 0.002(3) N2 0.021(4) 0.021(4) 0.021(3) -0.004(3) -0.002(3) 0.003(3) C1 0.022(5) 0.040(6) 0.036(4) 0.002(4) 0.010(3) 0.002(4) C2 0.031(4) 0.030(4) 0.021(3) -0.007(3) 0.001(3) 0.009(3) C3 0.025(4) 0.017(4) 0.036(5) -0.002(4) 0.002(3) 0.000(3) C4 0.026(5) 0.029(5) 0.029(4) 0.003(4) -0.001(3) -0.008(4) C5 0.033(6) 0.023(5) 0.048(5) -0.007(4) 0.017(4) 0.003(4) C6 0.026(5) 0.030(6) 0.050(5) 0.003(5) 0.003(4) 0.003(4) C7 0.030(5) 0.029(5) 0.028(4) 0.002(4) -0.006(3) 0.005(4) C8 0.037(5) 0.026(5) 0.025(4) -0.004(4) 0.002(3) 0.003(4) C9 0.013(5) 0.025(5) 0.026(5) -0.002(4) 0.001(3) -0.004(4) C10 0.040(6) 0.012(5) 0.018(4) 0.008(4) 0.008(4) 0.003(4) C11 0.025(5) 0.014(5) 0.014(4) 0.000(4) 0.002(3) 0.002(4) C12 0.018(5) 0.020(5) 0.029(5) -0.008(5) 0.001(4) -0.003(4) C13 0.027(5) 0.020(5) 0.032(5) -0.004(5) 0.002(4) 0.000(4) C14 0.030(5) 0.015(5) 0.035(5) 0.008(4) -0.001(4) 0.002(4) C15 0.023(6) 0.028(6) 0.046(6) -0.014(5) -0.008(4) 0.001(4) C16 0.030(6) 0.024(6) 0.041(6) -0.019(5) 0.005(4) 0.001(5) C17 0.023(5) 0.030(6) 0.022(4) -0.004(4) -0.004(4) -0.005(5) C18 0.034(5) 0.018(4) 0.036(4) -0.001(4) -0.001(3) -0.001(4) C19 0.028(4) 0.019(3) 0.021(3) 0.002(3) -0.001(3) 0.000(3) C20 0.016(4) 0.018(4) 0.036(4) -0.009(4) 0.002(3) -0.005(3) C21 0.021(4) 0.029(5) 0.031(4) 0.008(4) -0.002(3) -0.002(4) C22 0.039(6) 0.046(6) 0.015(4) -0.006(4) 0.004(4) -0.002(5) C23 0.036(5) 0.013(4) 0.028(4) 0.003(4) 0.017(4) 0.008(4) C24 0.022(4) 0.028(5) 0.040(5) 0.010(4) -0.006(3) 0.007(4) C25 0.036(5) 0.032(5) 0.022(4) -0.003(4) 0.002(3) -0.007(4) C26 0.022(5) 0.013(5) 0.021(5) 0.001(4) -0.005(3) -0.010(4) C27 0.008(5) 0.029(6) 0.033(5) -0.003(5) -0.003(3) -0.001(4) C28 0.015(5) 0.028(6) 0.017(4) 0.003(4) -0.002(3) -0.004(4) C29 0.015(5) 0.016(5) 0.016(4) 0.000(4) -0.001(3) -0.001(4) C30 0.022(5) 0.028(6) 0.019(4) -0.006(4) 0.003(3) -0.001(4) C31 0.029(5) 0.027(6) 0.032(5) 0.005(4) -0.014(4) 0.001(4) C32 0.022(5) 0.021(5) 0.043(5) 0.001(5) 0.007(4) 0.012(4) C33 0.018(5) 0.034(6) 0.033(5) -0.006(5) 0.002(4) -0.002(5) C34 0.024(5) 0.014(5) 0.027(4) 0.001(4) 0.002(4) 0.001(4) _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 O3 1.484(5) . ? P1 O4 1.524(5) . ? P1 O5 1.581(5) . ? P1 C11 1.825(8) . ? P2 O8 1.497(5) . ? P2 O9 1.504(5) . ? P2 O10 1.577(5) . ? P2 C28 1.813(9) . ? O1 C9 1.325(9) . ? O1 H1 0.8400 . ? O2 C9 1.228(8) . ? O5 H5 0.8400 . ? O6 C26 1.209(8) . ? O7 C26 1.317(9) . ? O7 H7 0.8400 . ? O10 H10 0.8400 . ? O11 H0W1 0.99(4) . ? O11 H0W2 0.96(4) . ? O12 H0W3 0.88(4) . ? O12 H0W4 0.86(4) . ? N1 C2 1.499(8) . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? N2 C19 1.513(8) . ? N2 H2A 0.9100 . ? N2 H2B 0.9100 . ? N2 H2C 0.9100 . ? C1 C2 1.506(9) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.513(10) . ? C2 H2 1.0000 . ? C3 C4 1.375(11) . ? C3 C8 1.391(10) . ? C4 C5 1.367(12) . ? C4 H4 0.9500 . ? C5 C6 1.401(11) . ? C5 H5 0.9500 . ? C6 C7 1.332(11) . ? C6 H6 0.9500 . ? C7 C8 1.375(11) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.528(11) . ? C10 C11 1.526(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.500(11) . ? C11 H11 1.0000 . ? C12 C13 1.378(11) . ? C12 C17 1.407(11) . ? C13 C14 1.382(12) . ? C13 H13 0.9500 . ? C14 C15 1.390(10) . ? C14 H14 0.9500 . ? C15 C16 1.363(12) . ? C15 H15 0.9500 . ? C16 C17 1.403(12) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.521(9) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.496(9) . ? C19 H19 1.0000 . ? C20 C21 1.395(10) . ? C20 C25 1.404(10) . ? C21 C22 1.363(12) . ? C21 H21 0.9500 . ? C22 C23 1.380(11) . ? C22 H22 0.9500 . ? C23 C24 1.408(11) . ? C23 H23 0.9500 . ? C24 C25 1.393(11) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.482(10) . ? C27 C28 1.552(9) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.523(11) . ? C28 H28 1.0000 . ? C29 C34 1.382(10) . ? C29 C30 1.403(10) . ? C30 C31 1.399(12) . ? C30 H30 0.9500 . ? C31 C32 1.370(10) . ? C31 H31 0.9500 . ? C32 C33 1.405(11) . ? C32 H32 0.9500 . ? C33 C34 1.359(11) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 P1 O4 115.9(3) . . ? O3 P1 O5 107.9(3) . . ? O4 P1 O5 110.3(3) . . ? O3 P1 C11 110.0(4) . . ? O4 P1 C11 107.3(3) . . ? O5 P1 C11 104.9(3) . . ? O8 P2 O9 115.9(3) . . ? O8 P2 O10 108.6(3) . . ? O9 P2 O10 110.4(3) . . ? O8 P2 C28 108.6(4) . . ? O9 P2 C28 107.9(3) . . ? O10 P2 C28 104.8(3) . . ? C9 O1 H1 109.5 . . ? P1 O5 H5 109.5 . . ? C26 O7 H7 109.5 . . ? P2 O10 H10 109.5 . . ? H0W1 O11 H0W2 105(5) . . ? H0W3 O12 H0W4 106(5) . . ? C2 N1 H1A 109.5 . . ? C2 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C2 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C19 N2 H2A 109.5 . . ? C19 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C19 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C1 109.6(5) . . ? N1 C2 C3 111.2(5) . . ? C1 C2 C3 112.7(6) . . ? N1 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C4 C3 C8 119.1(8) . . ? C4 C3 C2 116.6(7) . . ? C8 C3 C2 124.3(7) . . ? C5 C4 C3 121.0(8) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 119.4(9) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 119.2(9) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 122.5(8) . . ? C6 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? C7 C8 C3 118.7(8) . . ? C7 C8 H8 120.6 . . ? C3 C8 H8 120.6 . . ? O2 C9 O1 124.7(7) . . ? O2 C9 C10 123.2(7) . . ? O1 C9 C10 112.1(6) . . ? C11 C10 C9 114.9(6) . . ? C11 C10 H10A 108.5 . . ? C9 C10 H10A 108.5 . . ? C11 C10 H10B 108.5 . . ? C9 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C10 112.1(7) . . ? C12 C11 P1 109.2(6) . . ? C10 C11 P1 109.9(5) . . ? C12 C11 H11 108.5 . . ? C10 C11 H11 108.5 . . ? P1 C11 H11 108.5 . . ? C13 C12 C17 117.7(8) . . ? C13 C12 C11 123.0(7) . . ? C17 C12 C11 119.2(7) . . ? C12 C13 C14 121.0(8) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C15 120.4(8) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 120.5(9) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 118.8(8) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C16 C17 C12 121.5(8) . . ? C16 C17 H17 119.2 . . ? C12 C17 H17 119.2 . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C19 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 N2 110.1(5) . . ? C20 C19 C18 114.7(6) . . ? N2 C19 C18 110.0(5) . . ? C20 C19 H19 107.3 . . ? N2 C19 H19 107.3 . . ? C18 C19 H19 107.3 . . ? C21 C20 C25 117.3(8) . . ? C21 C20 C19 123.7(7) . . ? C25 C20 C19 118.9(7) . . ? C22 C21 C20 121.2(8) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 121.3(8) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C22 C23 C24 119.8(8) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C25 C24 C23 118.0(8) . . ? C25 C24 H24 121.0 . . ? C23 C24 H24 121.0 . . ? C24 C25 C20 122.3(8) . . ? C24 C25 H25 118.9 . . ? C20 C25 H25 118.9 . . ? O6 C26 O7 123.5(8) . . ? O6 C26 C27 124.0(7) . . ? O7 C26 C27 112.3(6) . . ? C26 C27 C28 112.6(7) . . ? C26 C27 H27A 109.1 . . ? C28 C27 H27A 109.1 . . ? C26 C27 H27B 109.1 . . ? C28 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C29 C28 C27 112.8(7) . . ? C29 C28 P2 109.5(5) . . ? C27 C28 P2 110.4(5) . . ? C29 C28 H28 108.0 . . ? C27 C28 H28 108.0 . . ? P2 C28 H28 108.0 . . ? C34 C29 C30 118.2(8) . . ? C34 C29 C28 121.0(7) . . ? C30 C29 C28 120.8(7) . . ? C31 C30 C29 120.2(8) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C32 C31 C30 120.8(8) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C33 118.1(8) . . ? C31 C32 H32 120.9 . . ? C33 C32 H32 120.9 . . ? C34 C33 C32 121.5(8) . . ? C34 C33 H33 119.3 . . ? C32 C33 H33 119.3 . . ? C33 C34 C29 121.2(8) . . ? C33 C34 H34 119.4 . . ? C29 C34 H34 119.4 . . ? 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 O1 H1 O4 0.84 1.71 2.543(7) 171.6 1_455 O5 H5 O9 0.84 1.87 2.633(6) 151.2 . O7 H7 O9 0.84 1.74 2.575(7) 172.3 1_655 O10 H10 O4 0.84 1.80 2.611(6) 161.7 . N1 H1A O12 0.91 2.07 2.870(8) 145.8 . N1 H1B O11 0.91 1.97 2.781(8) 147.7 . N1 H1C O2 0.91 2.05 2.945(8) 168.7 . N2 H2A O12 0.91 1.91 2.787(8) 161.1 1_656 N2 H2B O11 0.91 2.12 2.920(8) 146.5 1_656 N2 H2B O5 0.91 2.60 3.141(8) 119.1 1_655 N2 H2C O6 0.91 2.11 2.881(7) 142.0 . O11 H0W1 O3 0.99(4) 1.73(4) 2.713(7) 169(6) 1_554 O11 H0W2 O8 0.96(4) 1.75(4) 2.696(7) 167(7) . O12 H0W3 O8 0.88(4) 1.95(5) 2.719(7) 145(6) 1_455 O12 H0W4 O3 0.86(4) 1.88(4) 2.723(8) 167(9) 1_454 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.308 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.067 data_1140xx _database_code_CSD 177847 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H41 N2 O3 P' _chemical_formula_weight 544.65 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.716(2) _cell_length_b 10.737(2) _cell_length_c 26.151(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3008.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9453 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3082 _diffrn_reflns_av_R_equivalents 0.0052 _diffrn_reflns_av_sigmaI/netI 0.2018 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2996 _reflns_number_gt 1471 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0468P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(3) _refine_ls_number_reflns 2996 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2081 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1381 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 0.1402(2) 0.35878(17) 0.03821(8) 0.0270(5) Uani 1 1 d . . . N1 N 0.0242(6) 0.3050(5) 0.0742(2) 0.0238(15) Uani 1 1 d . . . N2 N 0.1927(5) 0.4554(5) 0.0828(2) 0.0288(16) Uani 1 1 d . . . O1 O 0.2335(4) 0.2700(4) 0.01744(16) 0.0292(13) Uani 1 1 d . . . O2 O 0.0880(5) 0.5178(5) -0.11962(19) 0.0418(16) Uani 1 1 d . . . O3 O -0.0344(5) 0.3575(5) -0.14359(16) 0.0372(14) Uani 1 1 d . . . C1 C -0.0446(7) 0.1916(6) 0.0616(3) 0.033(2) Uani 1 1 d . . . H1A H -0.0343 0.1743 0.0247 0.040 Uiso 1 1 calc R . . H1B H -0.1345 0.2064 0.0680 0.040 Uiso 1 1 calc R . . C2 C -0.0045(5) 0.0772(4) 0.09159(17) 0.0267(19) Uani 1 1 d G . . C3 C 0.1171(5) 0.0333(4) 0.08742(18) 0.040(2) Uani 1 1 d G . . H3 H 0.1755 0.0756 0.0663 0.048 Uiso 1 1 calc R . . C4 C 0.1534(4) -0.0726(5) 0.1142(2) 0.046(2) Uani 1 1 d G . . H4 H 0.2365 -0.1026 0.1113 0.055 Uiso 1 1 calc R . . C5 C 0.0680(6) -0.1345(4) 0.14506(18) 0.055(3) Uani 1 1 d G . . H5 H 0.0928 -0.2069 0.1633 0.066 Uiso 1 1 calc R . . C6 C -0.0535(6) -0.0906(5) 0.14924(17) 0.048(3) Uani 1 1 d G . . H6 H -0.1119 -0.1329 0.1704 0.058 Uiso 1 1 calc R . . C7 C -0.0898(4) 0.0153(5) 0.12250(19) 0.042(2) Uani 1 1 d G . . H7 H -0.1729 0.0453 0.1254 0.050 Uiso 1 1 calc R . . C8 C 0.2756(7) 0.5592(7) 0.0706(3) 0.035(2) Uani 1 1 d . . . H8A H 0.2304 0.6380 0.0771 0.043 Uiso 1 1 calc R . . H8B H 0.2954 0.5561 0.0337 0.043 Uiso 1 1 calc R . . C9 C 0.3973(3) 0.5613(4) 0.10053(16) 0.0268(19) Uani 1 1 d G . . C10 C 0.4549(4) 0.4511(3) 0.11536(17) 0.032(2) Uani 1 1 d G . . H10 H 0.4161 0.3733 0.1084 0.039 Uiso 1 1 calc R . . C11 C 0.5692(4) 0.4545(4) 0.14042(17) 0.0294(19) Uani 1 1 d G . . H11 H 0.6086 0.3792 0.1506 0.035 Uiso 1 1 calc R . . C12 C 0.6260(3) 0.5683(5) 0.15063(15) 0.0309(19) Uani 1 1 d G . . H12 H 0.7042 0.5706 0.1678 0.037 Uiso 1 1 calc R . . C13 C 0.5684(4) 0.6785(3) 0.13580(17) 0.030(2) Uani 1 1 d G . . H13 H 0.6072 0.7562 0.1428 0.036 Uiso 1 1 calc R . . C14 C 0.4541(4) 0.6750(3) 0.11074(17) 0.031(2) Uani 1 1 d G . . H14 H 0.4147 0.7503 0.1006 0.038 Uiso 1 1 calc R . . C15 C 0.0990(7) 0.4730(6) 0.1233(2) 0.0255(19) Uani 1 1 d . . . H15 H 0.0363 0.5354 0.1113 0.031 Uiso 1 1 calc R . . C16 C 0.1446(8) 0.5121(7) 0.1764(3) 0.040(2) Uani 1 1 d . . . H16A H 0.2026 0.4491 0.1904 0.048 Uiso 1 1 calc R . . H16B H 0.1886 0.5931 0.1746 0.048 Uiso 1 1 calc R . . C17 C 0.0287(8) 0.5229(7) 0.2100(3) 0.045(2) Uani 1 1 d . . . H17A H 0.0550 0.5430 0.2454 0.054 Uiso 1 1 calc R . . H17B H -0.0233 0.5926 0.1975 0.054 Uiso 1 1 calc R . . C18 C -0.0499(9) 0.4046(8) 0.2110(3) 0.053(3) Uani 1 1 d . . . H18A H -0.1276 0.4214 0.2302 0.063 Uiso 1 1 calc R . . H18B H -0.0034 0.3390 0.2295 0.063 Uiso 1 1 calc R . . C19 C -0.0843(7) 0.3556(8) 0.1576(3) 0.040(2) Uani 1 1 d . . . H19A H -0.1239 0.2725 0.1603 0.048 Uiso 1 1 calc R . . H19B H -0.1437 0.4130 0.1407 0.048 Uiso 1 1 calc R . . C20 C 0.0360(7) 0.3470(7) 0.1268(2) 0.0265(18) Uani 1 1 d . . . H20 H 0.0937 0.2888 0.1450 0.032 Uiso 1 1 calc R . . C21 C 0.0750(7) 0.4481(6) -0.0150(2) 0.0290(19) Uani 1 1 d . . . H21 H 0.1463 0.4965 -0.0296 0.035 Uiso 1 1 calc R . . C22 C -0.0207(4) 0.5443(3) 0.00196(16) 0.0242(18) Uani 1 1 d G . . C23 C -0.1418(5) 0.5094(3) 0.01450(17) 0.0271(18) Uani 1 1 d G . . H23 H -0.1685 0.4261 0.0091 0.033 Uiso 1 1 calc R . . C24 C -0.2238(4) 0.5965(4) 0.03494(18) 0.035(2) Uani 1 1 d G . . H24 H -0.3066 0.5726 0.0435 0.042 Uiso 1 1 calc R . . C25 C -0.1848(4) 0.7184(4) 0.04285(17) 0.035(2) Uani 1 1 d G . . H25 H -0.2408 0.7779 0.0568 0.042 Uiso 1 1 calc R . . C26 C -0.0637(5) 0.7533(3) 0.03032(17) 0.034(2) Uani 1 1 d G . . H26 H -0.0370 0.8366 0.0357 0.040 Uiso 1 1 calc R . . C27 C 0.0184(4) 0.6662(4) 0.00988(16) 0.0274(19) Uani 1 1 d G . . H27 H 0.1012 0.6901 0.0013 0.033 Uiso 1 1 calc R . . C28 C 0.0286(7) 0.3620(6) -0.0586(2) 0.0298(19) Uani 1 1 d . . . H28A H 0.0816 0.2865 -0.0597 0.036 Uiso 1 1 calc R . . H28B H -0.0578 0.3354 -0.0510 0.036 Uiso 1 1 calc R . . C29 C 0.0313(7) 0.4240(7) -0.1103(3) 0.0292(19) Uani 1 1 d . . . C30 C -0.0378(9) 0.3889(7) -0.1982(3) 0.039(2) Uani 1 1 d . . . C31 C 0.0876(8) 0.3789(8) -0.2218(3) 0.054(3) Uani 1 1 d . . . H31A H 0.1411 0.4459 -0.2089 0.081 Uiso 1 1 calc R . . H31B H 0.0801 0.3860 -0.2590 0.081 Uiso 1 1 calc R . . H31C H 0.1246 0.2981 -0.2131 0.081 Uiso 1 1 calc R . . C32 C -0.0958(8) 0.5141(7) -0.2072(3) 0.047(3) Uani 1 1 d . . . H32A H -0.1784 0.5168 -0.1912 0.070 Uiso 1 1 calc R . . H32B H -0.1041 0.5284 -0.2441 0.070 Uiso 1 1 calc R . . H32C H -0.0426 0.5789 -0.1923 0.070 Uiso 1 1 calc R . . C33 C -0.1245(9) 0.2870(7) -0.2187(3) 0.052(3) Uani 1 1 d . . . H33A H -0.0872 0.2051 -0.2123 0.078 Uiso 1 1 calc R . . H33B H -0.1363 0.2984 -0.2556 0.078 Uiso 1 1 calc R . . H33C H -0.2055 0.2923 -0.2014 0.078 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 0.0247(12) 0.0276(10) 0.0287(10) 0.0006(10) 0.0014(10) 0.0023(11) N1 0.017(4) 0.025(3) 0.029(3) 0.007(3) -0.001(3) -0.005(3) N2 0.032(4) 0.031(4) 0.023(3) 0.002(3) 0.000(3) -0.005(3) O1 0.029(3) 0.025(3) 0.034(3) -0.001(2) 0.011(3) 0.013(3) O2 0.056(4) 0.033(3) 0.037(3) 0.004(3) 0.004(3) -0.018(3) O3 0.052(4) 0.040(3) 0.020(2) 0.001(2) -0.003(3) -0.015(3) C1 0.027(5) 0.034(4) 0.038(5) 0.006(4) 0.000(4) -0.012(4) C2 0.031(5) 0.029(4) 0.020(4) -0.001(3) -0.006(4) -0.001(4) C3 0.037(6) 0.028(4) 0.054(5) 0.004(4) -0.004(5) -0.002(4) C4 0.047(6) 0.034(5) 0.057(6) -0.004(4) -0.017(5) 0.005(5) C5 0.090(8) 0.025(5) 0.050(6) 0.005(4) -0.023(6) 0.000(6) C6 0.074(8) 0.036(5) 0.035(5) 0.002(4) 0.001(6) -0.006(5) C7 0.056(6) 0.029(4) 0.041(5) -0.006(4) 0.007(5) -0.008(5) C8 0.033(5) 0.036(5) 0.038(5) 0.008(4) -0.008(4) -0.007(5) C9 0.023(5) 0.024(4) 0.033(4) 0.003(3) 0.001(4) 0.000(4) C10 0.031(5) 0.025(4) 0.042(5) 0.002(4) 0.000(4) 0.005(4) C11 0.028(5) 0.029(4) 0.032(4) 0.004(4) -0.004(4) 0.009(4) C12 0.023(5) 0.044(5) 0.026(4) -0.005(4) -0.004(4) 0.002(5) C13 0.028(5) 0.032(5) 0.029(4) -0.004(3) 0.003(4) -0.005(4) C14 0.028(5) 0.033(4) 0.033(4) 0.001(4) 0.006(4) -0.001(4) C15 0.031(5) 0.026(4) 0.020(4) 0.005(3) -0.002(4) 0.013(4) C16 0.048(6) 0.041(5) 0.030(4) -0.004(4) -0.014(5) 0.004(5) C17 0.065(7) 0.040(5) 0.030(4) 0.002(4) 0.006(5) -0.002(5) C18 0.065(7) 0.053(6) 0.041(5) -0.002(4) 0.018(5) 0.005(6) C19 0.035(5) 0.037(5) 0.049(5) 0.000(4) 0.018(4) 0.013(5) C20 0.019(4) 0.037(5) 0.023(4) -0.007(4) -0.003(4) 0.016(4) C21 0.030(5) 0.026(4) 0.031(4) 0.000(3) -0.003(4) -0.008(4) C22 0.023(5) 0.024(4) 0.026(4) 0.004(3) -0.006(4) 0.001(4) C23 0.031(5) 0.019(4) 0.031(4) 0.003(3) -0.003(4) 0.005(4) C24 0.015(4) 0.043(5) 0.047(5) -0.001(4) -0.002(4) 0.000(4) C25 0.032(5) 0.038(5) 0.036(5) 0.000(4) 0.000(4) 0.010(4) C26 0.034(6) 0.034(4) 0.033(5) -0.003(4) -0.015(4) 0.002(4) C27 0.023(5) 0.029(5) 0.030(4) 0.004(3) 0.001(4) -0.003(4) C28 0.038(5) 0.017(4) 0.035(4) 0.004(3) 0.001(4) -0.004(4) C29 0.029(5) 0.023(4) 0.036(5) 0.000(4) -0.006(4) 0.001(4) C30 0.053(6) 0.043(5) 0.023(4) 0.002(4) -0.001(4) -0.009(5) C31 0.066(7) 0.062(6) 0.034(5) 0.005(5) 0.003(5) 0.000(6) C32 0.049(7) 0.056(6) 0.035(5) 0.006(4) 0.001(5) 0.009(5) C33 0.074(8) 0.049(5) 0.033(5) 0.006(4) -0.010(5) -0.016(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 1.484(4) . ? P1 N2 1.658(6) . ? P1 N1 1.664(6) . ? P1 C21 1.828(7) . ? N1 C20 1.453(8) . ? N1 C1 1.461(8) . ? N2 C8 1.459(8) . ? N2 C15 1.473(8) . ? O2 C29 1.201(8) . ? O3 C29 1.329(8) . ? O3 C30 1.467(8) . ? C1 C2 1.519(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? 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 C9 1.521(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.3900 . ? C9 C14 1.3900 . ? C10 C11 1.3900 . ? C10 H10 0.9500 . ? C11 C12 1.3900 . ? C11 H11 0.9500 . ? C12 C13 1.3900 . ? C12 H12 0.9500 . ? C13 C14 1.3900 . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.515(9) . ? C15 C16 1.530(9) . ? C15 H15 1.0000 . ? C16 C17 1.526(10) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.524(11) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.538(10) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.522(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20 1.0000 . ? C21 C22 1.522(8) . ? C21 C28 1.550(8) . ? C21 H21 1.0000 . ? C22 C23 1.3900 . ? C22 C27 1.3900 . ? C23 C24 1.3900 . ? C23 H23 0.9500 . ? 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 H27 0.9500 . ? C28 C29 1.506(9) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C30 C31 1.484(11) . ? C30 C32 1.499(10) . ? C30 C33 1.532(10) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 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 P1 N2 115.5(3) . . ? O1 P1 N1 119.2(3) . . ? N2 P1 N1 94.2(3) . . ? O1 P1 C21 108.4(3) . . ? N2 P1 C21 109.6(3) . . ? N1 P1 C21 109.1(3) . . ? C20 N1 C1 121.0(6) . . ? C20 N1 P1 111.3(5) . . ? C1 N1 P1 122.6(5) . . ? C8 N2 C15 118.3(6) . . ? C8 N2 P1 122.1(5) . . ? C15 N2 P1 110.8(4) . . ? C29 O3 C30 121.9(6) . . ? N1 C1 C2 114.5(5) . . ? N1 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? N1 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C7 120.0 . . ? C3 C2 C1 120.0(4) . . ? C7 C2 C1 120.0(4) . . ? 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 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.0 . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C2 120.0 . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? N2 C8 C9 114.9(5) . . ? N2 C8 H8A 108.5 . . ? C9 C8 H8A 108.5 . . ? N2 C8 H8B 108.5 . . ? C9 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C10 C9 C14 120.0 . . ? C10 C9 C8 120.8(4) . . ? C14 C9 C8 119.2(4) . . ? C11 C10 C9 120.0 . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.0 . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 120.0 . . ? C13 C14 H14 120.0 . . ? C9 C14 H14 120.0 . . ? N2 C15 C20 103.5(5) . . ? N2 C15 C16 118.1(6) . . ? C20 C15 C16 109.5(6) . . ? N2 C15 H15 108.5 . . ? C20 C15 H15 108.5 . . ? C16 C15 H15 108.5 . . ? C17 C16 C15 106.5(6) . . ? C17 C16 H16A 110.4 . . ? C15 C16 H16A 110.4 . . ? C17 C16 H16B 110.4 . . ? C15 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? C18 C17 C16 113.3(6) . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 C19 113.8(7) . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18B 108.8 . . ? C19 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C18 107.3(7) . . ? C20 C19 H19A 110.2 . . ? C18 C19 H19A 110.2 . . ? C20 C19 H19B 110.2 . . ? C18 C19 H19B 110.2 . . ? H19A C19 H19B 108.5 . . ? N1 C20 C15 105.0(5) . . ? N1 C20 C19 116.5(6) . . ? C15 C20 C19 110.8(6) . . ? N1 C20 H20 108.1 . . ? C15 C20 H20 108.1 . . ? C19 C20 H20 108.1 . . ? C22 C21 C28 113.7(6) . . ? C22 C21 P1 113.1(4) . . ? C28 C21 P1 111.7(5) . . ? C22 C21 H21 105.8 . . ? C28 C21 H21 105.8 . . ? P1 C21 H21 105.8 . . ? C23 C22 C27 120.0 . . ? C23 C22 C21 121.0(4) . . ? C27 C22 C21 118.7(4) . . ? C24 C23 C22 120.0 . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.0 . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C26 C25 C24 120.0 . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 120.0 . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C26 C27 C22 120.0 . . ? C26 C27 H27 120.0 . . ? C22 C27 H27 120.0 . . ? C29 C28 C21 113.0(6) . . ? C29 C28 H28A 109.0 . . ? C21 C28 H28A 109.0 . . ? C29 C28 H28B 109.0 . . ? C21 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? O2 C29 O3 125.8(7) . . ? O2 C29 C28 124.3(7) . . ? O3 C29 C28 109.9(6) . . ? O3 C30 C31 111.4(7) . . ? O3 C30 C32 111.7(6) . . ? C31 C30 C32 112.0(7) . . ? O3 C30 C33 101.0(6) . . ? C31 C30 C33 110.6(7) . . ? C32 C30 C33 109.5(7) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 O1 P1 N1 C20 112.4(5) . . . . ? N2 P1 N1 C20 -10.0(5) . . . . ? C21 P1 N1 C20 -122.4(5) . . . . ? O1 P1 N1 C1 -42.6(6) . . . . ? N2 P1 N1 C1 -165.0(5) . . . . ? C21 P1 N1 C1 82.5(6) . . . . ? O1 P1 N2 C8 72.7(6) . . . . ? N1 P1 N2 C8 -162.1(5) . . . . ? C21 P1 N2 C8 -50.1(6) . . . . ? O1 P1 N2 C15 -140.6(4) . . . . ? N1 P1 N2 C15 -15.4(5) . . . . ? C21 P1 N2 C15 96.6(5) . . . . ? C20 N1 C1 C2 -52.4(8) . . . . ? P1 N1 C1 C2 100.3(6) . . . . ? N1 C1 C2 C3 -61.2(7) . . . . ? N1 C1 C2 C7 119.9(5) . . . . ? C7 C2 C3 C4 0.0 . . . . ? C1 C2 C3 C4 -178.9(5) . . . . ? 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 178.9(5) . . . . ? C15 N2 C8 C9 90.9(7) . . . . ? P1 N2 C8 C9 -124.7(6) . . . . ? N2 C8 C9 C10 32.7(7) . . . . ? N2 C8 C9 C14 -150.5(5) . . . . ? C14 C9 C10 C11 0.0 . . . . ? C8 C9 C10 C11 176.8(5) . . . . ? C9 C10 C11 C12 0.0 . . . . ? C10 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C9 0.0 . . . . ? C10 C9 C14 C13 0.0 . . . . ? C8 C9 C14 C13 -176.8(5) . . . . ? C8 N2 C15 C20 -177.5(6) . . . . ? P1 N2 C15 C20 34.4(6) . . . . ? C8 N2 C15 C16 -56.4(8) . . . . ? P1 N2 C15 C16 155.4(5) . . . . ? N2 C15 C16 C17 -179.9(6) . . . . ? C20 C15 C16 C17 -62.0(8) . . . . ? C15 C16 C17 C18 55.2(9) . . . . ? C16 C17 C18 C19 -52.3(10) . . . . ? C17 C18 C19 C20 51.3(9) . . . . ? C1 N1 C20 C15 -173.5(6) . . . . ? P1 N1 C20 C15 31.0(6) . . . . ? C1 N1 C20 C19 -50.5(9) . . . . ? P1 N1 C20 C19 154.0(5) . . . . ? N2 C15 C20 N1 -39.7(6) . . . . ? C16 C15 C20 N1 -166.4(6) . . . . ? N2 C15 C20 C19 -166.2(6) . . . . ? C16 C15 C20 C19 67.0(8) . . . . ? C18 C19 C20 N1 -178.6(6) . . . . ? C18 C19 C20 C15 -58.7(8) . . . . ? O1 P1 C21 C22 -179.0(4) . . . . ? N2 P1 C21 C22 -52.1(6) . . . . ? N1 P1 C21 C22 49.8(5) . . . . ? O1 P1 C21 C28 51.1(6) . . . . ? N2 P1 C21 C28 178.0(5) . . . . ? N1 P1 C21 C28 -80.1(6) . . . . ? C28 C21 C22 C23 51.0(6) . . . . ? P1 C21 C22 C23 -77.8(5) . . . . ? C28 C21 C22 C27 -135.7(5) . . . . ? P1 C21 C22 C27 95.5(4) . . . . ? C27 C22 C23 C24 0.0 . . . . ? C21 C22 C23 C24 173.3(5) . . . . ? C22 C23 C24 C25 0.0 . . . . ? C23 C24 C25 C26 0.0 . . . . ? C24 C25 C26 C27 0.0 . . . . ? C25 C26 C27 C22 0.0 . . . . ? C23 C22 C27 C26 0.0 . . . . ? C21 C22 C27 C26 -173.4(4) . . . . ? C22 C21 C28 C29 77.4(8) . . . . ? P1 C21 C28 C29 -153.0(5) . . . . ? C30 O3 C29 O2 4.2(12) . . . . ? C30 O3 C29 C28 -173.8(7) . . . . ? C21 C28 C29 O2 15.9(11) . . . . ? C21 C28 C29 O3 -166.1(6) . . . . ? C29 O3 C30 C31 62.8(9) . . . . ? C29 O3 C30 C32 -63.3(10) . . . . ? C29 O3 C30 C33 -179.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.401 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.075 # CIF produced by WinGX routine CIF_UPDATE # Created on 1999-10-25 at 17:38:49 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1beta3 # Request file : c:\wingx\files\archive.dat # CIF files read : acs99 dreduc struct psi_scan data_acs99 _database_code_CSD 177848 _audit_creation_date 1999-10-25T17:38:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1beta3 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core2.1beta.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H12 O5 P1' _chemical_formula_structural 'C9 H12 O5 P' _chemical_formula_sum 'C9 H11 O5 P' _chemical_formula_weight 230.15 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.6710(10) _cell_length_b 12.779(2) _cell_length_c 14.064(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1019.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 393(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour transparent _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.5 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_factor_muR 0.02 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 1 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.8889 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_correction_T_ave 0.915 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 393(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.1828E-2 _diffrn_orient_matrix_ub_12 -0.75183E-1 _diffrn_orient_matrix_ub_13 -0.19708E-1 _diffrn_orient_matrix_ub_21 -0.17008E-1 _diffrn_orient_matrix_ub_22 0.21666E-1 _diffrn_orient_matrix_ub_23 -0.67996E-1 _diffrn_orient_matrix_ub_31 0.175499 _diffrn_orient_matrix_ub_32 0.1314E-2 _diffrn_orient_matrix_ub_33 -0.6629E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 28 _diffrn_standards_decay_corr_max 1.395 _diffrn_standards_decay_corr_min 0.982 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 3 -6 -1 -5 -5 _diffrn_reflns_number 2053 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0955 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1788 _reflns_number_gt 1311 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1998)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 _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_number_reflns 1788 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1085 _refine_ls_R_factor_gt 0.056 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_diff_density_max 0.369 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.079 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 0.2234(2) 0.25817(10) 0.12671(9) 0.0209(4) Uani 1 1 d . . . O1 O 0.0408(6) 0.3314(3) 0.0869(2) 0.0258(9) Uani 1 1 d . . . O2 O 0.4536(7) 0.3190(3) 0.1516(3) 0.0294(10) Uani 1 1 d . . . O3 O 0.2899(9) 0.1659(3) 0.0617(4) 0.0371(13) Uani 1 1 d . . . O4 O -0.3566(8) 0.0052(3) 0.2843(3) 0.0374(12) Uani 1 1 d . . . O5 O 0.0164(8) 0.0176(4) 0.3349(3) 0.0329(11) Uani 1 1 d . . . C1 C 0.1195(10) 0.1918(4) 0.2326(4) 0.0234(13) Uani 1 1 d . . . C2 C -0.1035(11) 0.1317(4) 0.2115(4) 0.0255(13) Uani 1 1 d . . . C3 C -0.1603(10) 0.0455(4) 0.2821(4) 0.0243(14) Uani 1 1 d . . . C4 C 0.0992(9) 0.2685(4) 0.3157(3) 0.0246(13) Uani 1 1 d . . . C5 C -0.0924(12) 0.3337(5) 0.3255(4) 0.0280(14) Uani 1 1 d . . . C6 C -0.1071(13) 0.4035(5) 0.4005(4) 0.0340(16) Uani 1 1 d . . . C7 C 0.0682(13) 0.4087(5) 0.4672(4) 0.0361(16) Uani 1 1 d . . . C8 C 0.2602(15) 0.3442(5) 0.4579(4) 0.0420(17) Uani 1 1 d . . . C9 C 0.2763(11) 0.2752(5) 0.3819(4) 0.0313(13) Uani 1 1 d . . . H1 H 0.229(9) 0.138(4) 0.249(3) 0.012(12) Uiso 1 1 d . . . H2 H -0.110(9) 0.103(4) 0.148(4) 0.019(14) Uiso 1 1 d . . . H3 H -0.258(13) 0.184(5) 0.207(4) 0.040(17) Uiso 1 1 d . . . H4 H 0.404(9) 0.229(4) 0.375(4) 0.017(13) Uiso 1 1 d . . . H5 H 0.381(12) 0.346(5) 0.500(4) 0.033(18) Uiso 1 1 d . . . H6 H 0.058(11) 0.459(5) 0.521(4) 0.034(17) Uiso 1 1 d . . . H7 H -0.226(10) 0.438(4) 0.412(4) 0.017(15) Uiso 1 1 d . . . H8 H -0.197(12) 0.323(5) 0.293(4) 0.03(2) Uiso 1 1 d . . . H9 H 0.422(12) 0.386(6) 0.166(5) 0.040(19) Uiso 1 1 d . . . H10 H 0.339(10) 0.178(4) 0.023(4) 0.005(17) Uiso 1 1 d . . . H11 H -0.033(12) -0.028(5) 0.358(5) 0.03(2) 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 P1 0.0241(7) 0.0203(7) 0.0183(6) 0.0010(6) 0.0023(6) 0.0007(6) O1 0.030(2) 0.028(2) 0.0198(19) -0.0056(17) -0.0059(16) -0.0001(19) O2 0.022(2) 0.028(2) 0.038(3) 0.0033(19) 0.0041(17) 0.0034(18) O3 0.057(3) 0.024(2) 0.030(3) -0.0001(19) 0.023(3) -0.008(2) O4 0.025(3) 0.038(3) 0.049(3) 0.009(2) 0.006(2) -0.001(2) O5 0.040(3) 0.024(2) 0.035(2) 0.010(2) -0.006(2) -0.008(2) C1 0.029(3) 0.023(3) 0.019(3) 0.001(2) 0.001(2) 0.004(3) C2 0.031(4) 0.027(3) 0.019(3) 0.001(2) -0.006(2) 0.000(3) C3 0.031(4) 0.022(3) 0.020(3) -0.004(2) 0.000(2) 0.001(3) C4 0.029(3) 0.027(3) 0.018(3) 0.004(2) 0.003(2) -0.002(3) C5 0.034(4) 0.024(3) 0.026(3) 0.002(3) 0.001(3) -0.002(3) C6 0.040(4) 0.028(3) 0.034(4) -0.004(3) 0.017(3) 0.002(3) C7 0.057(5) 0.030(4) 0.021(3) -0.003(3) 0.000(3) -0.017(4) C8 0.057(5) 0.051(4) 0.018(3) 0.006(3) -0.009(3) -0.017(4) C9 0.025(3) 0.041(3) 0.028(3) 0.006(3) -0.004(3) -0.001(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.503(4) . ? P1 O3 1.539(5) . ? P1 O2 1.559(4) . ? P1 C1 1.811(5) . ? P1 H10 1.89(6) . ? O2 H9 0.90(7) . ? O3 H10 0.63(5) . ? O4 C3 1.227(7) . ? O5 C3 1.297(7) . ? O5 H11 0.72(7) . ? C1 C2 1.510(8) . ? C1 C4 1.530(8) . ? C1 H1 0.96(5) . ? C2 C3 1.518(8) . ? C2 H2 0.97(6) . ? C2 H3 1.10(7) . ? C4 C9 1.372(8) . ? C4 C5 1.376(8) . ? C5 C6 1.384(8) . ? C5 H8 0.76(6) . ? C6 C7 1.368(9) . ? C6 H7 0.83(6) . ? C7 C8 1.372(10) . ? C7 H6 0.99(6) . ? C8 C9 1.389(9) . ? C8 H5 0.91(6) . ? C9 H4 0.94(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 O1 P1 O3 115.1(2) . . ? O1 P1 O2 110.5(2) . . ? O3 P1 O2 108.1(3) . . ? O1 P1 C1 111.9(2) . . ? O3 P1 C1 102.1(3) . . ? O2 P1 C1 108.7(2) . . ? O1 P1 H10 106.7(16) . . ? O3 P1 H10 17.5(17) . . ? O2 P1 H10 98.7(17) . . ? C1 P1 H10 119.5(17) . . ? P1 O2 H9 111(4) . . ? P1 O3 H10 115(5) . . ? C3 O5 H11 100(5) . . ? C2 C1 C4 114.4(5) . . ? C2 C1 P1 110.4(4) . . ? C4 C1 P1 110.7(4) . . ? C2 C1 H1 103(3) . . ? C4 C1 H1 109(3) . . ? P1 C1 H1 109(3) . . ? C1 C2 C3 114.7(5) . . ? C1 C2 H2 114(3) . . ? C3 C2 H2 109(3) . . ? C1 C2 H3 112(3) . . ? C3 C2 H3 108(3) . . ? H2 C2 H3 99(4) . . ? O4 C3 O5 124.8(5) . . ? O4 C3 C2 120.9(5) . . ? O5 C3 C2 114.2(5) . . ? C9 C4 C5 118.1(5) . . ? C9 C4 C1 120.2(5) . . ? C5 C4 C1 121.6(5) . . ? C4 C5 C6 121.0(6) . . ? C4 C5 H8 117(5) . . ? C6 C5 H8 121(5) . . ? C7 C6 C5 120.6(7) . . ? C7 C6 H7 116(4) . . ? C5 C6 H7 123(4) . . ? C6 C7 C8 118.9(6) . . ? C6 C7 H6 121(4) . . ? C8 C7 H6 120(4) . . ? C7 C8 C9 120.4(6) . . ? C7 C8 H5 122(4) . . ? C9 C8 H5 118(4) . . ? C4 C9 C8 120.9(6) . . ? C4 C9 H4 117(3) . . ? C8 C9 H4 122(3) . . ?