# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/425 data_9b _publ_requested_journal 'JCS Perkin Trans. 1' _publ_contact_author ; Prof. Rainer Schobert School of Chemistry, The Queen's University of Belfast Belfast BT9 5AG Northern Ireland ; _publ_contact_letter ; Please consider this CIF submission for publication as a Paper in JCS Perkin Trans 1. ; _publ_contact_author_phone '(44) 1232 382117' _publ_contact_author_fax '(44) 1232 274425' _publ_contact_author_email 'r.schobert@qub.ac.uk' loop_ _publ_author_name _publ_author_address 'Schobert, Rainer' ; School of Chemistry, The Queen's University of Belfast Belfast BT9 5AG Northern ; 'Siegfried, Sven' ; School of Chemistry, The Queen's University of Belfast Belfast BT9 5AG Northern ; 'Nieuwenhuyzen, Mark' ; School of Chemistry, The Queen's University of Belfast Belfast BT9 5AG Northern ; 'Milius, Wolfgang' ; Laboratorium fuerr Anorganische Chemie Universitaetsstr. 30 95440 Bayreuth Germany ; 'Hampel, Frank' ; Institut fuer Organische Chemie der Universitaet Henkestrasse 42 91054 Erlangen Germany ; _publ_section_title ; Selective C-acylation of CH-active dicarbonyl compounds with keteneylidenetriphenylphosphorane: syntheses and structures of 3-acylylidene-tetronic acids, 3-acylylidene-4-hydroxy-coumarins, and 4-acylylidene-pyrazol-5-ones ; data_schob1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H25 O4 P' _chemical_formula_weight 432.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0470(11) _cell_length_b 13.6137(12) _cell_length_c 18.555(2) _cell_angle_alpha 97.040(8) _cell_angle_beta 104.117(9) _cell_angle_gamma 106.888(8) _cell_volume 2303.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min 5.93 _cell_measurement_theta_max 13.99 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9558 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8050 _reflns_number_gt 5866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+1.8823P] 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 0.0147(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 8050 _refine_ls_number_parameters 561 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1719 _refine_ls_wR_factor_gt 0.1504 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 -0.20506(8) 0.51868(6) 0.31319(4) 0.0433(2) Uani 1 1 d . . . O1 O -0.4101(2) 0.62614(19) 0.32490(13) 0.0636(6) Uani 1 1 d . . . H'1 H -0.4741 0.6766 0.3316 0.080 Uiso 1 1 d R . . O2 O -0.5184(3) 0.7454(2) 0.37038(17) 0.0799(8) Uani 1 1 d . . . O3 O -0.1759(4) 0.8362(4) 0.5706(2) 0.1409(17) Uani 1 1 d . . . O4 O -0.0391(3) 0.7955(3) 0.50481(15) 0.0892(9) Uani 1 1 d . . . C1 C -0.3384(3) 0.3956(2) 0.31184(17) 0.0481(7) Uani 1 1 d . . . C2 C -0.4417(4) 0.3946(3) 0.3500(2) 0.0730(11) Uani 1 1 d . . . H2A H -0.4430 0.4593 0.3765 0.080 Uiso 1 1 d R . . C3 C -0.5427(5) 0.3000(4) 0.3496(3) 0.0938(14) Uani 1 1 d . . . H3A H -0.6135 0.2995 0.3763 0.080 Uiso 1 1 d R . . C4 C -0.5426(5) 0.2078(3) 0.3119(3) 0.0852(13) Uani 1 1 d . . . H4A H -0.6140 0.1428 0.3113 0.080 Uiso 1 1 d R . . C5 C -0.4400(5) 0.2076(3) 0.2745(2) 0.0755(11) Uani 1 1 d . . . H5A H -0.4400 0.1426 0.2477 0.080 Uiso 1 1 d R . . C6 C -0.3370(4) 0.3010(3) 0.27534(19) 0.0610(9) Uani 1 1 d . . . H6A H -0.2636 0.3003 0.2507 0.080 Uiso 1 1 d R . . C7 C -0.0312(3) 0.4983(2) 0.33583(16) 0.0438(7) Uani 1 1 d . . . C8 C 0.0620(3) 0.5217(2) 0.29165(18) 0.0505(7) Uani 1 1 d . . . H8A H 0.0300 0.5410 0.2440 0.080 Uiso 1 1 d R . . C9 C 0.2013(4) 0.5177(3) 0.3163(2) 0.0600(9) Uani 1 1 d . . . H9A H 0.2658 0.5342 0.2856 0.080 Uiso 1 1 d R . . C10 C 0.2476(4) 0.4908(3) 0.3840(2) 0.0673(10) Uani 1 1 d . . . H10A H 0.3457 0.4908 0.4016 0.080 Uiso 1 1 d R . . C11 C 0.1543(4) 0.4632(4) 0.4272(2) 0.0780(12) Uani 1 1 d . . . H11A H 0.1862 0.4422 0.4741 0.080 Uiso 1 1 d R . . C12 C 0.0142(4) 0.4656(3) 0.4024(2) 0.0676(10) Uani 1 1 d . . . H12A H -0.0518 0.4447 0.4317 0.080 Uiso 1 1 d R . . C13 C -0.2404(3) 0.5488(2) 0.21942(16) 0.0461(7) Uani 1 1 d . . . C14 C -0.2870(4) 0.4705(3) 0.15408(17) 0.0544(8) Uani 1 1 d . . . H14A H -0.3072 0.3982 0.1578 0.080 Uiso 1 1 d R . . C15 C -0.3037(4) 0.4977(3) 0.08373(19) 0.0663(10) Uani 1 1 d . . . H15A H -0.3340 0.4439 0.0388 0.080 Uiso 1 1 d R . . C16 C -0.2771(4) 0.6005(3) 0.0778(2) 0.0687(10) Uani 1 1 d . . . H16A H -0.2909 0.6183 0.0287 0.080 Uiso 1 1 d R . . C17 C -0.2318(4) 0.6779(3) 0.1421(2) 0.0694(10) Uani 1 1 d . . . H17A H -0.2122 0.7500 0.1379 0.080 Uiso 1 1 d R . . C18 C -0.2131(4) 0.6526(3) 0.21274(19) 0.0580(8) Uani 1 1 d . . . H18A H -0.1816 0.7069 0.2575 0.080 Uiso 1 1 d R . . C19 C -0.1848(3) 0.6211(2) 0.38415(16) 0.0481(7) Uani 1 1 d . . . H19A H -0.0969 0.6470 0.4259 0.080 Uiso 1 1 d R . . C20 C -0.2905(3) 0.6669(2) 0.38279(17) 0.0490(7) Uani 1 1 d . . . C21 C -0.2873(4) 0.7523(3) 0.44000(19) 0.0543(8) Uani 1 1 d . . . C22 C -0.4075(4) 0.7862(3) 0.4293(2) 0.0672(10) Uani 1 1 d . . . C23 C -0.4220(6) 0.8720(4) 0.4831(3) 0.1061(16) Uani 1 1 d . . . H23A H -0.5145 0.8807 0.4633 0.080 Uiso 1 1 d R . . H23B H -0.4155 0.8533 0.5318 0.080 Uiso 1 1 d R . . H23C H -0.3454 0.9365 0.4885 0.080 Uiso 1 1 d R . . C24 C -0.1654(5) 0.8000(3) 0.5087(2) 0.0770(11) Uani 1 1 d . . . C25 C 0.0850(5) 0.8386(5) 0.5726(3) 0.119(2) Uani 1 1 d . . . H25A H 0.0964 0.9109 0.5921 0.143 Uiso 1 1 calc R . . H25B H 0.0692 0.7989 0.6115 0.143 Uiso 1 1 calc R . . C26 C 0.2092(6) 0.8336(7) 0.5548(3) 0.164(3) Uani 1 1 d . . . H26A H 0.2915 0.8626 0.5994 0.246 Uiso 1 1 calc R . . H26B H 0.2243 0.8731 0.5163 0.246 Uiso 1 1 calc R . . H26C H 0.1980 0.7618 0.5364 0.246 Uiso 1 1 calc R . . P2 P 0.25538(7) 0.81042(5) 0.13922(4) 0.0379(2) Uani 1 1 d . . . O5 O 0.2405(2) 0.75437(17) -0.01956(12) 0.0501(5) Uani 1 1 d . . . H'2 H 0.2232 0.7365 -0.0804 0.080 Uiso 1 1 d R . . O6 O 0.1501(3) 0.7236(2) -0.15573(13) 0.0658(6) Uani 1 1 d . . . O7 O -0.0938(5) 0.9159(3) -0.1143(2) 0.1250(14) Uani 1 1 d . . . O8 O -0.1448(3) 0.8221(2) -0.03033(16) 0.0719(7) Uani 1 1 d . . . C27 C 0.4453(3) 0.8884(2) 0.16174(17) 0.0458(7) Uani 1 1 d . . . C28 C 0.4932(4) 0.9454(3) 0.1104(2) 0.0572(8) Uani 1 1 d . . . H28A H 0.4250 0.9463 0.0644 0.080 Uiso 1 1 d R . . C29 C 0.6397(4) 1.0012(3) 0.1260(3) 0.0789(12) Uani 1 1 d . . . H29A H 0.6728 1.0421 0.0912 0.080 Uiso 1 1 d R . . C30 C 0.7367(4) 0.9980(3) 0.1905(3) 0.0877(13) Uani 1 1 d . . . H30A H 0.8386 1.0345 0.1999 0.080 Uiso 1 1 d R . . C31 C 0.6911(4) 0.9438(3) 0.2418(3) 0.0838(13) Uani 1 1 d . . . H31A H 0.7608 0.9433 0.2874 0.080 Uiso 1 1 d R . . C32 C 0.5434(4) 0.8890(3) 0.2285(2) 0.0629(9) Uani 1 1 d . . . H32A H 0.5107 0.8522 0.2653 0.080 Uiso 1 1 d R . . C33 C 0.1968(3) 0.8437(2) 0.22067(15) 0.0399(6) Uani 1 1 d . . . C34 C 0.1975(4) 0.7841(3) 0.27576(17) 0.0514(7) Uani 1 1 d . . . H34A H 0.2283 0.7238 0.2704 0.080 Uiso 1 1 d R . . C35 C 0.1540(4) 0.8108(3) 0.33854(19) 0.0646(9) Uani 1 1 d . . . H35A H 0.1550 0.7691 0.3767 0.080 Uiso 1 1 d R . . C36 C 0.1099(4) 0.8967(3) 0.34630(19) 0.0637(9) Uani 1 1 d . . . H36A H 0.0781 0.9146 0.3894 0.080 Uiso 1 1 d R . . C37 C 0.1112(4) 0.9571(3) 0.29249(19) 0.0650(9) Uani 1 1 d . . . H37A H 0.0822 1.0181 0.2988 0.080 Uiso 1 1 d R . . C38 C 0.1540(4) 0.9317(3) 0.22903(18) 0.0555(8) Uani 1 1 d . . . H38A H 0.1538 0.9742 0.1914 0.080 Uiso 1 1 d R . . C39 C 0.2460(3) 0.6746(2) 0.12914(15) 0.0383(6) Uani 1 1 d . . . C40 C 0.3676(3) 0.6425(2) 0.14396(19) 0.0536(8) Uani 1 1 d . . . H40A H 0.4632 0.6941 0.1601 0.080 Uiso 1 1 d R . . C41 C 0.3516(4) 0.5379(3) 0.1356(2) 0.0619(9) Uani 1 1 d . . . H41A H 0.4364 0.5168 0.1469 0.080 Uiso 1 1 d R . . C42 C 0.2160(4) 0.4630(3) 0.11140(19) 0.0574(8) Uani 1 1 d . . . H42A H 0.2055 0.3898 0.1047 0.080 Uiso 1 1 d R . . C43 C 0.0941(4) 0.4941(2) 0.0963(2) 0.0576(8) Uani 1 1 d . . . H43A H -0.0012 0.4422 0.0798 0.080 Uiso 1 1 d R . . C44 C 0.1090(3) 0.5982(2) 0.10507(18) 0.0508(7) Uani 1 1 d . . . H44A H 0.0238 0.6188 0.0945 0.080 Uiso 1 1 d R . . C45 C 0.1413(3) 0.8326(2) 0.06199(16) 0.0427(6) Uani 1 1 d . . . H45A H 0.0769 0.8702 0.0698 0.080 Uiso 1 1 d R . . C46 C 0.1413(3) 0.7975(2) -0.01112(16) 0.0396(6) Uani 1 1 d . . . C47 C 0.0427(3) 0.8051(2) -0.07993(16) 0.0416(6) Uani 1 1 d . . . C48 C 0.0523(4) 0.7649(2) -0.15033(17) 0.0507(7) Uani 1 1 d . . . C49 C -0.0532(5) 0.7606(3) -0.2246(2) 0.0737(11) Uani 1 1 d . . . H49A H -0.0260 0.7302 -0.2658 0.080 Uiso 1 1 d R . . H49B H -0.1495 0.7187 -0.2264 0.080 Uiso 1 1 d R . . H49C H -0.0516 0.8304 -0.2290 0.080 Uiso 1 1 d R . . C50 C -0.0687(4) 0.8546(2) -0.07755(18) 0.0523(8) Uani 1 1 d . . . C51 C -0.2539(5) 0.8688(4) -0.0213(3) 0.0990(15) Uani 1 1 d . . . H51A H -0.2406 0.9302 -0.0431 0.080 Uiso 1 1 d R . . H51B H -0.2415 0.8904 0.0318 0.080 Uiso 1 1 d R . . C52 C -0.3976(5) 0.7976(4) -0.0577(4) 0.1163(19) Uani 1 1 d . . . H52A H -0.4671 0.8308 -0.0507 0.080 Uiso 1 1 d R . . H52B H -0.4107 0.7769 -0.1110 0.080 Uiso 1 1 d R . . H52C H -0.4116 0.7367 -0.0354 0.080 Uiso 1 1 d 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 0.0376(4) 0.0561(5) 0.0386(4) 0.0072(3) 0.0128(3) 0.0188(3) O1 0.0488(13) 0.0739(16) 0.0598(14) -0.0032(12) 0.0019(11) 0.0271(12) O2 0.0627(16) 0.0874(19) 0.097(2) 0.0147(16) 0.0154(15) 0.0438(15) O3 0.114(3) 0.199(4) 0.088(2) -0.047(3) 0.021(2) 0.059(3) O4 0.0573(16) 0.118(2) 0.0649(17) -0.0242(15) 0.0025(13) 0.0186(15) C1 0.0397(16) 0.0570(18) 0.0489(17) 0.0106(14) 0.0159(13) 0.0158(14) C2 0.062(2) 0.068(2) 0.102(3) 0.015(2) 0.046(2) 0.0232(19) C3 0.069(3) 0.091(3) 0.140(4) 0.033(3) 0.065(3) 0.023(2) C4 0.063(2) 0.068(3) 0.112(4) 0.020(2) 0.026(2) 0.001(2) C5 0.087(3) 0.058(2) 0.071(2) 0.0049(18) 0.020(2) 0.016(2) C6 0.071(2) 0.064(2) 0.0516(19) 0.0083(16) 0.0252(17) 0.0233(18) C7 0.0400(15) 0.0554(17) 0.0408(15) 0.0095(13) 0.0151(12) 0.0203(13) C8 0.0484(17) 0.0585(19) 0.0498(17) 0.0141(14) 0.0200(14) 0.0198(15) C9 0.0452(18) 0.072(2) 0.072(2) 0.0179(18) 0.0295(17) 0.0202(16) C10 0.0452(19) 0.089(3) 0.074(2) 0.016(2) 0.0162(17) 0.0342(19) C11 0.069(2) 0.125(4) 0.062(2) 0.039(2) 0.0201(19) 0.055(2) C12 0.057(2) 0.114(3) 0.055(2) 0.036(2) 0.0297(17) 0.044(2) C13 0.0389(15) 0.0610(19) 0.0418(16) 0.0094(14) 0.0119(12) 0.0221(14) C14 0.0566(19) 0.069(2) 0.0425(17) 0.0088(15) 0.0136(14) 0.0294(17) C15 0.072(2) 0.089(3) 0.0432(18) 0.0100(18) 0.0146(17) 0.040(2) C16 0.071(2) 0.101(3) 0.051(2) 0.029(2) 0.0211(18) 0.045(2) C17 0.076(2) 0.074(2) 0.068(2) 0.030(2) 0.0222(19) 0.032(2) C18 0.057(2) 0.063(2) 0.0527(19) 0.0107(16) 0.0136(16) 0.0214(17) C19 0.0433(16) 0.0620(19) 0.0386(15) 0.0046(14) 0.0099(13) 0.0214(14) C20 0.0433(16) 0.0577(18) 0.0445(16) 0.0073(14) 0.0122(13) 0.0164(14) C21 0.0515(18) 0.0570(19) 0.0556(19) 0.0042(15) 0.0193(15) 0.0200(15) C22 0.066(2) 0.064(2) 0.083(3) 0.0139(19) 0.030(2) 0.0312(19) C23 0.107(4) 0.099(3) 0.125(4) -0.004(3) 0.040(3) 0.059(3) C24 0.073(3) 0.088(3) 0.064(2) -0.016(2) 0.020(2) 0.031(2) C25 0.071(3) 0.165(5) 0.071(3) -0.027(3) -0.013(2) 0.015(3) C26 0.074(4) 0.294(10) 0.093(4) 0.046(5) 0.000(3) 0.033(5) P2 0.0344(4) 0.0392(4) 0.0405(4) 0.0071(3) 0.0117(3) 0.0129(3) O5 0.0463(11) 0.0616(13) 0.0516(12) 0.0097(10) 0.0194(10) 0.0282(10) O6 0.0795(17) 0.0757(16) 0.0546(14) 0.0109(12) 0.0335(12) 0.0340(14) O7 0.172(4) 0.147(3) 0.145(3) 0.100(3) 0.085(3) 0.124(3) O8 0.0593(15) 0.0735(16) 0.105(2) 0.0280(15) 0.0382(14) 0.0394(13) C27 0.0396(15) 0.0402(15) 0.0542(18) 0.0033(13) 0.0145(14) 0.0101(13) C28 0.0517(19) 0.0517(19) 0.064(2) 0.0083(16) 0.0235(16) 0.0078(15) C29 0.061(2) 0.065(2) 0.101(3) 0.013(2) 0.038(2) -0.0032(19) C30 0.047(2) 0.073(3) 0.121(4) 0.011(3) 0.021(2) -0.0044(19) C31 0.048(2) 0.077(3) 0.096(3) 0.007(2) -0.011(2) 0.0058(19) C32 0.0490(19) 0.058(2) 0.064(2) 0.0089(16) 0.0011(16) 0.0053(16) C33 0.0372(14) 0.0411(15) 0.0396(15) 0.0041(12) 0.0108(12) 0.0127(12) C34 0.0580(19) 0.0533(18) 0.0476(17) 0.0135(14) 0.0183(15) 0.0220(15) C35 0.081(2) 0.068(2) 0.0505(19) 0.0163(17) 0.0283(18) 0.0236(19) C36 0.070(2) 0.077(2) 0.0468(18) 0.0016(17) 0.0254(17) 0.0253(19) C37 0.081(2) 0.069(2) 0.053(2) 0.0006(17) 0.0205(18) 0.042(2) C38 0.072(2) 0.0531(19) 0.0487(18) 0.0104(14) 0.0194(16) 0.0305(17) C39 0.0377(14) 0.0409(15) 0.0384(14) 0.0079(11) 0.0134(12) 0.0147(12) C40 0.0383(16) 0.0502(18) 0.072(2) 0.0081(15) 0.0153(15) 0.0171(14) C41 0.063(2) 0.053(2) 0.082(2) 0.0145(17) 0.0257(19) 0.0336(17) C42 0.074(2) 0.0428(17) 0.064(2) 0.0126(15) 0.0311(18) 0.0225(17) C43 0.0551(19) 0.0439(17) 0.066(2) 0.0078(15) 0.0196(16) 0.0052(15) C44 0.0388(16) 0.0482(18) 0.0616(19) 0.0073(15) 0.0127(14) 0.0121(14) C45 0.0446(16) 0.0460(16) 0.0426(15) 0.0089(12) 0.0138(13) 0.0220(13) C46 0.0367(14) 0.0379(14) 0.0468(16) 0.0101(12) 0.0139(12) 0.0143(12) C47 0.0434(15) 0.0363(14) 0.0449(15) 0.0117(12) 0.0134(13) 0.0115(12) C48 0.061(2) 0.0432(16) 0.0457(17) 0.0121(13) 0.0166(15) 0.0126(15) C49 0.090(3) 0.068(2) 0.0475(19) 0.0074(17) 0.0062(19) 0.015(2) C50 0.0569(19) 0.0481(17) 0.0546(18) 0.0140(15) 0.0111(15) 0.0246(15) C51 0.072(3) 0.102(3) 0.145(4) 0.017(3) 0.042(3) 0.056(3) C52 0.061(3) 0.125(4) 0.166(6) 0.024(4) 0.023(3) 0.047(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 C19 1.724(3) . ? P1 C7 1.804(3) . ? P1 C1 1.809(3) . ? P1 C13 1.811(3) . ? O1 C20 1.320(4) . ? O2 C22 1.282(5) . ? O3 C24 1.233(5) . ? O4 C24 1.307(5) . ? O4 C25 1.452(5) . ? C1 C6 1.385(4) . ? C1 C2 1.389(4) . ? C2 C3 1.388(6) . ? C3 C4 1.360(6) . ? C4 C5 1.377(6) . ? C5 C6 1.382(5) . ? C7 C12 1.382(4) . ? C7 C8 1.385(4) . ? C8 C9 1.381(4) . ? C9 C10 1.362(5) . ? C10 C11 1.377(5) . ? C11 C12 1.382(5) . ? C13 C18 1.387(4) . ? C13 C14 1.393(4) . ? C14 C15 1.384(5) . ? C15 C16 1.369(5) . ? C16 C17 1.374(5) . ? C17 C18 1.378(5) . ? C19 C20 1.376(4) . ? C20 C21 1.463(4) . ? C21 C22 1.393(5) . ? C21 C24 1.457(5) . ? C22 C23 1.505(5) . ? C25 C26 1.384(8) . ? P2 C45 1.721(3) . ? P2 C33 1.804(3) . ? P2 C27 1.808(3) . ? P2 C39 1.808(3) . ? O5 C46 1.326(3) . ? O6 C48 1.283(4) . ? O7 C50 1.185(4) . ? O8 C50 1.331(4) . ? O8 C51 1.450(4) . ? C27 C32 1.379(4) . ? C27 C28 1.388(4) . ? C28 C29 1.383(5) . ? C29 C30 1.362(6) . ? C30 C31 1.359(6) . ? C31 C32 1.398(5) . ? C33 C34 1.381(4) . ? C33 C38 1.389(4) . ? C34 C35 1.385(4) . ? C35 C36 1.370(5) . ? C36 C37 1.369(5) . ? C37 C38 1.387(5) . ? C39 C44 1.390(4) . ? C39 C40 1.390(4) . ? C40 C41 1.371(4) . ? C41 C42 1.371(5) . ? C42 C43 1.385(5) . ? C43 C44 1.366(4) . ? C45 C46 1.382(4) . ? C46 C47 1.448(4) . ? C47 C48 1.390(4) . ? C47 C50 1.471(4) . ? C48 C49 1.503(5) . ? C51 C52 1.425(6) . ? 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 C19 P1 C7 104.48(14) . . ? C19 P1 C1 114.52(15) . . ? C7 P1 C1 106.17(14) . . ? C19 P1 C13 113.43(15) . . ? C7 P1 C13 107.90(13) . . ? C1 P1 C13 109.76(14) . . ? C24 O4 C25 118.6(3) . . ? C6 C1 C2 118.9(3) . . ? C6 C1 P1 121.2(2) . . ? C2 C1 P1 119.9(3) . . ? C3 C2 C1 119.8(4) . . ? C4 C3 C2 120.8(4) . . ? C3 C4 C5 119.9(4) . . ? C4 C5 C6 120.0(4) . . ? C5 C6 C1 120.5(3) . . ? C12 C7 C8 119.1(3) . . ? C12 C7 P1 118.6(2) . . ? C8 C7 P1 122.1(2) . . ? C9 C8 C7 120.0(3) . . ? C10 C9 C8 120.3(3) . . ? C9 C10 C11 120.4(3) . . ? C10 C11 C12 119.5(3) . . ? C7 C12 C11 120.4(3) . . ? C18 C13 C14 119.3(3) . . ? C18 C13 P1 119.2(2) . . ? C14 C13 P1 121.4(2) . . ? C15 C14 C13 119.5(3) . . ? C16 C15 C14 120.6(3) . . ? C15 C16 C17 120.1(3) . . ? C16 C17 C18 120.2(4) . . ? C17 C18 C13 120.2(3) . . ? C20 C19 P1 122.0(2) . . ? O1 C20 C19 116.1(3) . . ? O1 C20 C21 116.7(3) . . ? C19 C20 C21 127.1(3) . . ? C22 C21 C24 119.2(3) . . ? C22 C21 C20 118.5(3) . . ? C24 C21 C20 122.2(3) . . ? O2 C22 C21 121.5(3) . . ? O2 C22 C23 113.4(3) . . ? C21 C22 C23 125.1(4) . . ? O3 C24 O4 118.8(4) . . ? O3 C24 C21 124.6(4) . . ? O4 C24 C21 116.4(3) . . ? C26 C25 O4 109.3(4) . . ? C45 P2 C33 107.07(13) . . ? C45 P2 C27 115.18(14) . . ? C33 P2 C27 106.81(13) . . ? C45 P2 C39 112.53(13) . . ? C33 P2 C39 108.00(13) . . ? C27 P2 C39 106.92(13) . . ? C50 O8 C51 118.1(3) . . ? C32 C27 C28 119.9(3) . . ? C32 C27 P2 120.3(2) . . ? C28 C27 P2 119.7(2) . . ? C29 C28 C27 119.8(4) . . ? C30 C29 C28 120.0(4) . . ? C31 C30 C29 120.8(4) . . ? C30 C31 C32 120.4(4) . . ? C27 C32 C31 119.0(4) . . ? C34 C33 C38 119.6(3) . . ? C34 C33 P2 120.7(2) . . ? C38 C33 P2 119.7(2) . . ? C33 C34 C35 120.3(3) . . ? C36 C35 C34 120.1(3) . . ? C37 C36 C35 119.9(3) . . ? C36 C37 C38 121.0(3) . . ? C37 C38 C33 119.1(3) . . ? C44 C39 C40 118.4(3) . . ? C44 C39 P2 117.8(2) . . ? C40 C39 P2 123.8(2) . . ? C41 C40 C39 120.4(3) . . ? C42 C41 C40 120.7(3) . . ? C41 C42 C43 119.3(3) . . ? C44 C43 C42 120.3(3) . . ? C43 C44 C39 120.8(3) . . ? C46 C45 P2 121.1(2) . . ? O5 C46 C45 117.8(2) . . ? O5 C46 C47 116.8(2) . . ? C45 C46 C47 125.5(2) . . ? C48 C47 C46 119.8(3) . . ? C48 C47 C50 118.6(3) . . ? C46 C47 C50 121.6(3) . . ? O6 C48 C47 121.2(3) . . ? O6 C48 C49 115.1(3) . . ? C47 C48 C49 123.6(3) . . ? O7 C50 O8 121.4(3) . . ? O7 C50 C47 125.2(3) . . ? O8 C50 C47 113.4(3) . . ? C52 C51 O8 111.6(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 C19 P1 C1 C6 -160.1(3) . . . . ? C7 P1 C1 C6 -45.4(3) . . . . ? C13 P1 C1 C6 71.0(3) . . . . ? C19 P1 C1 C2 17.8(3) . . . . ? C7 P1 C1 C2 132.5(3) . . . . ? C13 P1 C1 C2 -111.1(3) . . . . ? C6 C1 C2 C3 -1.3(6) . . . . ? P1 C1 C2 C3 -179.2(3) . . . . ? C1 C2 C3 C4 -0.4(7) . . . . ? C2 C3 C4 C5 1.0(8) . . . . ? C3 C4 C5 C6 0.2(7) . . . . ? C4 C5 C6 C1 -1.9(6) . . . . ? C2 C1 C6 C5 2.4(5) . . . . ? P1 C1 C6 C5 -179.7(3) . . . . ? C19 P1 C7 C12 64.3(3) . . . . ? C1 P1 C7 C12 -57.1(3) . . . . ? C13 P1 C7 C12 -174.7(3) . . . . ? C19 P1 C7 C8 -110.8(3) . . . . ? C1 P1 C7 C8 127.8(3) . . . . ? C13 P1 C7 C8 10.2(3) . . . . ? C12 C7 C8 C9 -3.5(5) . . . . ? P1 C7 C8 C9 171.6(3) . . . . ? C7 C8 C9 C10 0.0(5) . . . . ? C8 C9 C10 C11 2.7(6) . . . . ? C9 C10 C11 C12 -1.8(7) . . . . ? C8 C7 C12 C11 4.4(6) . . . . ? P1 C7 C12 C11 -170.9(3) . . . . ? C10 C11 C12 C7 -1.8(7) . . . . ? C19 P1 C13 C18 15.9(3) . . . . ? C7 P1 C13 C18 -99.4(3) . . . . ? C1 P1 C13 C18 145.4(2) . . . . ? C19 P1 C13 C14 -167.6(2) . . . . ? C7 P1 C13 C14 77.2(3) . . . . ? C1 P1 C13 C14 -38.1(3) . . . . ? C18 C13 C14 C15 0.7(5) . . . . ? P1 C13 C14 C15 -175.9(2) . . . . ? C13 C14 C15 C16 -1.0(5) . . . . ? C14 C15 C16 C17 0.8(6) . . . . ? C15 C16 C17 C18 -0.1(6) . . . . ? C16 C17 C18 C13 -0.2(5) . . . . ? C14 C13 C18 C17 -0.1(5) . . . . ? P1 C13 C18 C17 176.5(3) . . . . ? C7 P1 C19 C20 173.6(3) . . . . ? C1 P1 C19 C20 -70.7(3) . . . . ? C13 P1 C19 C20 56.3(3) . . . . ? P1 C19 C20 O1 1.6(4) . . . . ? P1 C19 C20 C21 178.7(3) . . . . ? O1 C20 C21 C22 -1.2(5) . . . . ? C19 C20 C21 C22 -178.3(3) . . . . ? O1 C20 C21 C24 176.4(3) . . . . ? C19 C20 C21 C24 -0.6(6) . . . . ? C24 C21 C22 O2 -178.8(4) . . . . ? C20 C21 C22 O2 -1.1(5) . . . . ? C24 C21 C22 C23 1.5(6) . . . . ? C20 C21 C22 C23 179.2(4) . . . . ? C25 O4 C24 O3 -3.4(7) . . . . ? C25 O4 C24 C21 -177.9(4) . . . . ? C22 C21 C24 O3 29.8(7) . . . . ? C20 C21 C24 O3 -147.8(5) . . . . ? C22 C21 C24 O4 -156.0(4) . . . . ? C20 C21 C24 O4 26.3(6) . . . . ? C24 O4 C25 C26 -175.2(6) . . . . ? C45 P2 C27 C32 170.4(2) . . . . ? C33 P2 C27 C32 51.7(3) . . . . ? C39 P2 C27 C32 -63.7(3) . . . . ? C45 P2 C27 C28 -11.5(3) . . . . ? C33 P2 C27 C28 -130.3(3) . . . . ? C39 P2 C27 C28 114.3(3) . . . . ? C32 C27 C28 C29 1.1(5) . . . . ? P2 C27 C28 C29 -176.9(3) . . . . ? C27 C28 C29 C30 1.6(6) . . . . ? C28 C29 C30 C31 -2.6(7) . . . . ? C29 C30 C31 C32 1.0(7) . . . . ? C28 C27 C32 C31 -2.7(5) . . . . ? P2 C27 C32 C31 175.3(3) . . . . ? C30 C31 C32 C27 1.7(6) . . . . ? C45 P2 C33 C34 141.3(2) . . . . ? C27 P2 C33 C34 -94.8(3) . . . . ? C39 P2 C33 C34 19.9(3) . . . . ? C45 P2 C33 C38 -40.3(3) . . . . ? C27 P2 C33 C38 83.6(3) . . . . ? C39 P2 C33 C38 -161.8(2) . . . . ? C38 C33 C34 C35 0.9(5) . . . . ? P2 C33 C34 C35 179.3(3) . . . . ? C33 C34 C35 C36 0.0(5) . . . . ? C34 C35 C36 C37 -1.1(6) . . . . ? C35 C36 C37 C38 1.3(6) . . . . ? C36 C37 C38 C33 -0.4(6) . . . . ? C34 C33 C38 C37 -0.7(5) . . . . ? P2 C33 C38 C37 -179.1(3) . . . . ? C45 P2 C39 C44 -47.0(3) . . . . ? C33 P2 C39 C44 70.9(3) . . . . ? C27 P2 C39 C44 -174.4(2) . . . . ? C45 P2 C39 C40 132.9(3) . . . . ? C33 P2 C39 C40 -109.1(3) . . . . ? C27 P2 C39 C40 5.5(3) . . . . ? C44 C39 C40 C41 -0.6(5) . . . . ? P2 C39 C40 C41 179.4(3) . . . . ? C39 C40 C41 C42 1.0(5) . . . . ? C40 C41 C42 C43 -0.9(5) . . . . ? C41 C42 C43 C44 0.4(5) . . . . ? C42 C43 C44 C39 0.0(5) . . . . ? C40 C39 C44 C43 0.1(5) . . . . ? P2 C39 C44 C43 -180.0(3) . . . . ? C33 P2 C45 C46 -168.6(2) . . . . ? C27 P2 C45 C46 72.8(3) . . . . ? C39 P2 C45 C46 -50.1(3) . . . . ? P2 C45 C46 O5 -5.7(4) . . . . ? P2 C45 C46 C47 175.1(2) . . . . ? O5 C46 C47 C48 2.0(4) . . . . ? C45 C46 C47 C48 -178.8(3) . . . . ? O5 C46 C47 C50 -178.0(3) . . . . ? C45 C46 C47 C50 1.2(4) . . . . ? C46 C47 C48 O6 -2.0(4) . . . . ? C50 C47 C48 O6 178.0(3) . . . . ? C46 C47 C48 C49 174.5(3) . . . . ? C50 C47 C48 C49 -5.5(5) . . . . ? C51 O8 C50 O7 -3.8(6) . . . . ? C51 O8 C50 C47 177.7(3) . . . . ? C48 C47 C50 O7 -45.8(5) . . . . ? C46 C47 C50 O7 134.2(4) . . . . ? C48 C47 C50 O8 132.6(3) . . . . ? C46 C47 C50 O8 -47.4(4) . . . . ? C50 O8 C51 C52 107.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.707 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.052 data_sso3 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C31 H30 O4 P' _chemical_formula_weight 497.52 _chemical_melting_point ? _chemical_compound_source ? 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.351(3) _cell_length_b 12.9583(12) _cell_length_c 16.409(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.679(8) _cell_angle_gamma 90.00 _cell_volume 5237.7(10) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5 _cell_measurement_theta_max 12.5 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method none _exptl_crystal_F_000 2104 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type 'Psi Scans' _exptl_absorpt_correction_T_min 0.762 _exptl_absorpt_correction_T_max 0.779 _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Siemens P4' _diffrn_measurement_method 'Omega Scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1% _diffrn_reflns_number 4728 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0947 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4618 _reflns_number_observed 2810 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1993)' _computing_cell_refinement 'XSCANS (Fait, 1993)' _computing_data_reduction 'XSCANS (Fait, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL-PC (Sheldrick, 1995)' _computing_publication_material 'SHELXTL-PC (Sheldrick, 1995)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+6.7072P] 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 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4618 _refine_ls_number_parameters 330 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1227 _refine_ls_R_factor_obs 0.0611 _refine_ls_wR_factor_all 0.1310 _refine_ls_wR_factor_obs 0.1073 _refine_ls_goodness_of_fit_all 1.029 _refine_ls_goodness_of_fit_obs 1.105 _refine_ls_restrained_S_all 1.029 _refine_ls_restrained_S_obs 1.105 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.17356(4) 0.05021(7) 0.51638(6) 0.0197(2) Uani 1 d . . C1S C 0.0000 0.5247(5) 0.2500 0.048(2) Uani 1 d S . H1S H 0.0000 0.5980(5) 0.2500 0.058 Uiso 1 calc SR . C2S C -0.0036(2) 0.4740(4) 0.3208(3) 0.0628(14) Uani 1 d . . H2S H -0.0060(2) 0.5116(4) 0.3695(3) 0.075 Uiso 1 calc R . C3S C -0.0036(3) 0.3701(5) 0.3215(5) 0.114(3) Uani 1 d . . H3S H -0.0062(3) 0.3337(5) 0.3707(5) 0.137 Uiso 1 calc R . C4S C 0.0000 0.3167(7) 0.2500 0.155(7) Uani 1 d S . H4S H 0.0000 0.2434(7) 0.2500 0.186 Uiso 1 calc SR . C2 C 0.12712(13) -0.0458(3) 0.5206(2) 0.0208(8) Uani 1 d . . H2 H 0.11076(13) -0.0409(3) 0.5694(2) 0.025 Uiso 1 d R . C3 C 0.12265(13) -0.1309(3) 0.4678(2) 0.0202(8) Uani 1 d . . O3 O 0.15128(9) -0.1476(2) 0.41687(15) 0.0277(6) Uani 1 d . . C4 C 0.07724(14) -0.2115(3) 0.4704(2) 0.0231(8) Uani 1 d . . O5 O 0.03383(11) -0.1594(2) 0.5816(2) 0.0393(7) Uani 1 d . . C5 C 0.03288(14) -0.1645(3) 0.5078(2) 0.0268(9) Uani 1 d . . C6 C -0.0123(2) -0.1253(3) 0.4374(2) 0.0422(11) Uani 1 d . . H6A H -0.0192(2) -0.0595(3) 0.4491(2) 0.051 Uiso 1 d R . H6B H -0.0425(2) -0.1793(3) 0.4392(2) 0.051 Uiso 1 d R . C7 C 0.00614(15) -0.1454(3) 0.3574(2) 0.0377(10) Uani 1 d . . H7A H -0.02193(15) -0.1585(3) 0.3023(2) 0.045 Uiso 1 d R . H7B H 0.02887(15) -0.0790(3) 0.3430(2) 0.045 Uiso 1 d R . C8 C 0.04594(15) -0.2353(3) 0.3800(2) 0.0310(9) Uani 1 d . . H8A H 0.06813(15) -0.2561(3) 0.3409(2) 0.037 Uiso 1 d R . H8B H 0.02323(15) -0.2964(3) 0.3781(2) 0.037 Uiso 1 d R . C11 C 0.17201(14) 0.0870(3) 0.4098(2) 0.0230(8) Uani 1 d . . C12 C 0.2188(2) 0.1063(3) 0.3833(2) 0.0273(9) Uani 1 d . . H12 H 0.2527(14) 0.0993(27) 0.4228(22) 0.033 Uiso 1 d . . C13 C 0.2161(2) 0.1305(3) 0.3000(2) 0.0345(10) Uani 1 d . . H13 H 0.2520(2) 0.1624(3) 0.2800(2) 0.041 Uiso 1 d R . C14 C 0.1664(2) 0.1385(3) 0.2438(2) 0.0387(11) Uani 1 d . . H14 H 0.1635(2) 0.1619(3) 0.1777(2) 0.046 Uiso 1 d R . C15 C 0.1195(2) 0.1192(3) 0.2695(2) 0.0443(11) Uani 1 d . . H15 H 0.0804(2) 0.1423(3) 0.2333(2) 0.053 Uiso 1 d R . C16 C 0.1215(2) 0.0943(3) 0.3525(2) 0.0351(10) Uani 1 d . . H16 H 0.0916(2) 0.0826(3) 0.3756(2) 0.042 Uiso 1 d R . C21 C 0.15565(13) 0.1614(3) 0.5711(2) 0.0217(8) Uani 1 d . . C22 C 0.15660(14) 0.1503(3) 0.6561(2) 0.0272(9) Uani 1 d . . H22 H 0.17171(14) 0.0780(3) 0.6856(2) 0.033 Uiso 1 d R . C23 C 0.14087(15) 0.2323(3) 0.6994(2) 0.0350(10) Uani 1 d . . H23 H 0.14052(15) 0.2174(3) 0.7617(2) 0.042 Uiso 1 d R . C24 C 0.1236(2) 0.3232(3) 0.6580(3) 0.0429(11) Uani 1 d . . H24 H 0.1125(2) 0.3774(3) 0.6901(3) 0.051 Uiso 1 d R . C25 C 0.1220(2) 0.3343(3) 0.5738(3) 0.0405(11) Uani 1 d . . H25 H 0.1087(2) 0.3985(3) 0.5433(3) 0.049 Uiso 1 d R . C26 C 0.13834(14) 0.2533(3) 0.5300(2) 0.0304(9) Uani 1 d . . H26 H 0.13820(14) 0.2607(3) 0.4685(2) 0.036 Uiso 1 d R . C31 C 0.24290(13) 0.0194(3) 0.5670(2) 0.0204(8) Uani 1 d . . C32 C 0.35020(15) -0.0308(3) 0.6378(2) 0.0360(10) Uani 1 d . . H32 H 0.38657(15) -0.0615(3) 0.6631(2) 0.043 Uiso 1 d R . C33 C 0.27996(14) 0.0961(3) 0.6011(2) 0.0299(9) Uani 1 d . . H33 H 0.26713(14) 0.1768(3) 0.6029(2) 0.036 Uiso 1 d R . C34 C 0.33355(15) 0.0706(3) 0.6371(2) 0.0336(10) Uani 1 d . . H34 H 0.35920(15) 0.1172(3) 0.6546(2) 0.040 Uiso 1 d R . C35 C 0.31377(15) -0.1085(3) 0.6045(2) 0.0322(9) Uani 1 d . . H35 H 0.32012(15) -0.2008(3) 0.6045(2) 0.039 Uiso 1 d R . C36 C 0.25979(14) -0.0832(3) 0.5695(2) 0.0250(8) Uani 1 d . . H36 H 0.23165(14) -0.1400(3) 0.5418(2) 0.030 Uiso 1 d R . C41 C 0.0991(2) -0.3094(3) 0.5177(2) 0.0285(9) Uani 1 d . . O41 O 0.07471(11) -0.3888(2) 0.5115(2) 0.0453(8) Uani 1 d . . O42 O 0.14869(10) -0.2958(2) 0.5682(2) 0.0300(6) Uani 1 d . . C43 C 0.1717(2) -0.3867(3) 0.6164(3) 0.0398(11) Uani 1 d . . H43A H 0.1507(2) -0.4008(3) 0.6624(3) 0.048 Uiso 1 d R . H43B H 0.1718(2) -0.4400(3) 0.5745(3) 0.048 Uiso 1 d R . C44 C 0.2292(2) -0.3619(3) 0.6599(3) 0.0438(11) Uani 1 d . . H44A H 0.2445(4) -0.4189(10) 0.6973(13) 0.066 Uiso 1 calc R . H44B H 0.2300(2) -0.2986(12) 0.6927(13) 0.066 Uiso 1 calc R . H44C H 0.2507(3) -0.3521(20) 0.6181(3) 0.066 Uiso 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 0.0193(4) 0.0183(5) 0.0207(5) -0.0004(4) 0.0035(4) 0.0006(4) C1S 0.053(4) 0.033(4) 0.050(4) 0.000 -0.006(3) 0.000 C2S 0.062(3) 0.059(4) 0.068(4) 0.009(3) 0.018(3) 0.000(3) C3S 0.121(6) 0.064(5) 0.191(9) 0.055(5) 0.104(6) 0.018(4) C4S 0.179(12) 0.026(5) 0.322(20) 0.000 0.181(14) 0.000 C2 0.022(2) 0.020(2) 0.021(2) 0.000(2) 0.0074(15) -0.002(2) C3 0.019(2) 0.019(2) 0.021(2) 0.006(2) 0.002(2) 0.0037(15) O3 0.0289(14) 0.0262(14) 0.0319(14) -0.0037(12) 0.0147(12) -0.0025(12) C4 0.022(2) 0.024(2) 0.024(2) -0.005(2) 0.006(2) -0.004(2) O5 0.048(2) 0.040(2) 0.035(2) -0.0051(14) 0.0195(14) -0.0106(14) C5 0.027(2) 0.025(2) 0.031(2) -0.006(2) 0.011(2) -0.012(2) C6 0.027(2) 0.051(3) 0.044(3) -0.015(2) 0.000(2) 0.002(2) C7 0.025(2) 0.052(3) 0.030(2) -0.003(2) -0.004(2) 0.000(2) C8 0.031(2) 0.035(2) 0.026(2) -0.008(2) 0.004(2) -0.012(2) C11 0.028(2) 0.019(2) 0.021(2) 0.002(2) 0.003(2) 0.001(2) C12 0.032(2) 0.026(2) 0.025(2) 0.002(2) 0.008(2) 0.003(2) C13 0.049(3) 0.024(2) 0.033(2) 0.002(2) 0.016(2) -0.002(2) C14 0.064(3) 0.025(2) 0.026(2) 0.004(2) 0.008(2) -0.011(2) C15 0.047(3) 0.049(3) 0.029(2) 0.012(2) -0.007(2) -0.008(2) C16 0.032(2) 0.038(2) 0.034(2) 0.007(2) 0.005(2) -0.005(2) C21 0.017(2) 0.022(2) 0.026(2) -0.007(2) 0.003(2) -0.002(2) C22 0.022(2) 0.030(2) 0.029(2) -0.009(2) 0.005(2) -0.002(2) C23 0.029(2) 0.044(3) 0.031(2) -0.017(2) 0.006(2) -0.001(2) C24 0.034(2) 0.039(3) 0.057(3) -0.024(2) 0.013(2) 0.003(2) C25 0.041(3) 0.021(2) 0.058(3) -0.005(2) 0.010(2) 0.002(2) C26 0.030(2) 0.026(2) 0.037(2) -0.003(2) 0.011(2) -0.001(2) C31 0.020(2) 0.025(2) 0.017(2) 0.001(2) 0.0055(15) 0.000(2) C32 0.021(2) 0.052(3) 0.033(2) 0.010(2) 0.003(2) 0.009(2) C33 0.024(2) 0.027(2) 0.036(2) 0.003(2) 0.001(2) -0.003(2) C34 0.025(2) 0.041(3) 0.031(2) 0.002(2) 0.001(2) -0.008(2) C35 0.028(2) 0.039(2) 0.029(2) 0.005(2) 0.005(2) 0.006(2) C36 0.028(2) 0.024(2) 0.022(2) 0.001(2) 0.002(2) 0.001(2) C41 0.032(2) 0.024(2) 0.030(2) -0.006(2) 0.008(2) -0.004(2) O41 0.044(2) 0.024(2) 0.063(2) 0.0022(14) 0.0022(15) -0.0110(14) O42 0.034(2) 0.0202(14) 0.0310(15) 0.0035(12) -0.0011(12) -0.0008(12) C43 0.049(3) 0.033(2) 0.036(2) 0.007(2) 0.006(2) 0.004(2) C44 0.048(3) 0.035(3) 0.041(3) -0.006(2) -0.004(2) 0.015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C2 1.726(3) . ? P1 C31 1.802(3) . ? P1 C11 1.804(3) . ? P1 C21 1.811(3) . ? C1S C2S 1.355(5) 2 ? C1S C2S 1.355(5) . ? C2S C3S 1.347(7) . ? C3S C4S 1.384(8) . ? C4S C3S 1.384(8) 2 ? C2 C3 1.391(5) . ? C3 O3 1.248(4) . ? C3 C4 1.562(5) . ? C4 C41 1.522(5) . ? C4 C5 1.529(5) . ? C4 C8 1.539(5) . ? O5 C5 1.207(4) . ? C5 C6 1.509(5) . ? C6 C7 1.516(5) . ? C7 C8 1.528(5) . ? C11 C12 1.380(5) . ? C11 C16 1.402(5) . ? C12 C13 1.389(5) . ? C13 C14 1.378(5) . ? C14 C15 1.374(6) . ? C15 C16 1.390(5) . ? C21 C26 1.389(5) . ? C21 C22 1.395(5) . ? C22 C23 1.388(5) . ? C23 C24 1.380(6) . ? C24 C25 1.379(6) . ? C25 C26 1.390(5) . ? C31 C33 1.391(5) . ? C31 C36 1.394(5) . ? C32 C34 1.379(5) . ? C32 C35 1.388(5) . ? C33 C34 1.387(5) . ? C35 C36 1.392(5) . ? C41 O41 1.193(4) . ? C41 O42 1.343(4) . ? O42 C43 1.461(4) . ? C43 C44 1.500(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 P1 C31 114.9(2) . . ? C2 P1 C11 111.8(2) . . ? C31 P1 C11 107.5(2) . . ? C2 P1 C21 107.5(2) . . ? C31 P1 C21 106.2(2) . . ? C11 P1 C21 108.7(2) . . ? C2S C1S C2S 122.1(7) 2 . ? C3S C2S C1S 119.5(6) . . ? C2S C3S C4S 119.5(7) . . ? C3S C4S C3S 120.0(8) . 2 ? C3 C2 P1 120.2(3) . . ? O3 C3 C2 125.4(3) . . ? O3 C3 C4 116.9(3) . . ? C2 C3 C4 117.7(3) . . ? C41 C4 C5 110.0(3) . . ? C41 C4 C8 111.5(3) . . ? C5 C4 C8 101.9(3) . . ? C41 C4 C3 112.9(3) . . ? C5 C4 C3 111.2(3) . . ? C8 C4 C3 108.8(3) . . ? O5 C5 C6 125.5(4) . . ? O5 C5 C4 125.6(4) . . ? C6 C5 C4 108.9(3) . . ? C5 C6 C7 105.8(3) . . ? C6 C7 C8 104.0(3) . . ? C7 C8 C4 104.0(3) . . ? C12 C11 C16 119.6(3) . . ? C12 C11 P1 122.0(3) . . ? C16 C11 P1 118.4(3) . . ? C11 C12 C13 120.3(4) . . ? C14 C13 C12 120.0(4) . . ? C15 C14 C13 120.1(4) . . ? C14 C15 C16 120.7(4) . . ? C15 C16 C11 119.2(4) . . ? C26 C21 C22 120.2(3) . . ? C26 C21 P1 121.9(3) . . ? C22 C21 P1 117.8(3) . . ? C23 C22 C21 119.6(4) . . ? C24 C23 C22 119.8(4) . . ? C25 C24 C23 120.9(4) . . ? C24 C25 C26 119.9(4) . . ? C21 C26 C25 119.6(4) . . ? C33 C31 C36 119.7(3) . . ? C33 C31 P1 121.3(3) . . ? C36 C31 P1 118.9(3) . . ? C34 C32 C35 120.9(3) . . ? C34 C33 C31 120.1(4) . . ? C32 C34 C33 119.8(4) . . ? C32 C35 C36 119.3(4) . . ? C35 C36 C31 120.1(3) . . ? O41 C41 O42 123.8(4) . . ? O41 C41 C4 123.8(3) . . ? O42 C41 C4 112.3(3) . . ? C41 O42 C43 115.0(3) . . ? O42 C43 C44 107.6(3) . . ? _refine_diff_density_max 0.237 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.058 data_ss01 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C29 H21 O4 P' _chemical_formula_weight 464.43 _chemical_melting_point ? _chemical_compound_source ? 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.938(2) _cell_length_b 22.265(5) _cell_length_c 11.629(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.56(3) _cell_angle_gamma 90.00 _cell_volume 2303.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method ? _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.154 _exptl_absorpt_correction_type 'psi scans' _exptl_absorpt_correction_T_min 2.7 _exptl_absorpt_correction_T_max 11.0 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius Mach3 ' _diffrn_measurement_method 'theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 3 _diffrn_reflns_number 4312 _diffrn_reflns_av_R_equivalents 0.0697 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 24.98 _reflns_number_total 4043 _reflns_number_observed 2776 _reflns_observed_criterion >2sigma(I) _computing_data_collection Express _computing_cell_refinement Express _computing_data_reduction MoleN _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.8898P] 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 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4043 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_obs 0.0469 _refine_ls_wR_factor_all 0.1303 _refine_ls_wR_factor_obs 0.1086 _refine_ls_goodness_of_fit_all 1.053 _refine_ls_goodness_of_fit_obs 1.084 _refine_ls_restrained_S_all 1.053 _refine_ls_restrained_S_obs 1.084 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.05162(8) 0.87789(3) 0.94311(6) 0.0238(2) Uani 1 d . . O1 O 0.3836(2) 0.97065(9) 1.2032(2) 0.0324(5) Uani 1 d . . O2 O 0.4672(2) 0.93861(9) 1.3758(2) 0.0339(5) Uani 1 d . . O3 O 0.1568(2) 0.80416(10) 1.3690(2) 0.0436(6) Uani 1 d . . H3A H 0.1027(2) 0.80329(10) 1.3058(2) 0.065 Uiso 1 calc R . O4 O 0.0676(2) 0.82768(9) 1.1690(2) 0.0359(5) Uani 1 d . . C10 C 0.3694(3) 0.93259(12) 1.2757(2) 0.0274(6) Uani 1 d . . C11 C 0.4639(3) 0.90050(13) 1.4681(2) 0.0310(7) Uani 1 d . . C12 C 0.5691(4) 0.9109(2) 1.5614(3) 0.0400(8) Uani 1 d . . C13 C 0.5692(4) 0.8742(2) 1.6572(3) 0.0479(9) Uani 1 d . . C14 C 0.4673(4) 0.8273(2) 1.6588(3) 0.0496(9) Uani 1 d . . C15 C 0.3626(4) 0.81776(15) 1.5661(3) 0.0432(8) Uani 1 d . . C16 C 0.3598(3) 0.85480(12) 1.4683(2) 0.0305(7) Uani 1 d . . C17 C 0.2536(3) 0.84598(13) 1.3667(2) 0.0310(7) Uani 1 d . . C18 C 0.2628(3) 0.88371(12) 1.2703(2) 0.0259(6) Uani 1 d . . C19 C 0.1655(3) 0.87272(12) 1.1655(2) 0.0273(6) Uani 1 d . . C20 C 0.1672(3) 0.90240(12) 1.0624(2) 0.0255(6) Uani 1 d . . H20A H 0.2310(3) 0.93612(12) 1.0563(2) 0.031 Uiso 1 calc R . C30 C 0.0761(3) 0.92904(12) 0.8264(2) 0.0254(6) Uani 1 d . . C31 C -0.0426(3) 0.96103(14) 0.7698(2) 0.0335(7) Uani 1 d . . C32 C -0.0159(4) 0.99920(15) 0.6799(3) 0.0429(8) Uani 1 d . . C33 C 0.1279(4) 1.00589(15) 0.6474(3) 0.0437(8) Uani 1 d . . C34 C 0.2458(4) 0.9742(2) 0.7033(3) 0.0424(8) Uani 1 d . . C35 C 0.2203(3) 0.93542(14) 0.7919(3) 0.0342(7) Uani 1 d . . C40 C 0.1030(3) 0.80513(12) 0.8903(2) 0.0276(6) Uani 1 d . . C41 C 0.0406(4) 0.7864(2) 0.7814(3) 0.0412(8) Uani 1 d . . C42 C 0.0820(4) 0.7323(2) 0.7371(3) 0.0523(9) Uani 1 d . . H42A H 0.0375(4) 0.7193(2) 0.6639(3) 0.063 Uiso 1 calc R . C43 C 0.1878(5) 0.6970(2) 0.7986(4) 0.0568(10) Uani 1 d . . C44 C 0.2513(4) 0.7152(2) 0.9052(4) 0.0554(10) Uani 1 d . . C45 C 0.2082(4) 0.76931(14) 0.9519(3) 0.0398(8) Uani 1 d . . C50 C -0.1439(3) 0.87727(12) 0.9687(2) 0.0235(6) Uani 1 d . . C51 C -0.1995(3) 0.92688(13) 1.0222(3) 0.0325(7) Uani 1 d . . C52 C -0.3487(3) 0.92900(14) 1.0436(3) 0.0347(7) Uani 1 d . . C53 C -0.4411(3) 0.88069(14) 1.0117(2) 0.0314(7) Uani 1 d . . C54 C -0.3856(3) 0.83119(14) 0.9597(2) 0.0296(6) Uani 1 d . . C55 C -0.2367(3) 0.82904(13) 0.9372(2) 0.0266(6) Uani 1 d . . H53 H -0.5418(32) 0.8802(12) 1.0278(22) 0.025(7) Uiso 1 d . . H55 H -0.1935(30) 0.7929(12) 0.9034(22) 0.026(7) Uiso 1 d . . H52 H -0.3883(31) 0.9624(13) 1.0788(25) 0.031(8) Uiso 1 d . . H45 H 0.2514(32) 0.7814(13) 1.0291(26) 0.033(8) Uiso 1 d . . H51 H -0.1378(31) 0.9587(13) 1.0406(24) 0.028(8) Uiso 1 d . . H34 H 0.3437(36) 0.9773(14) 0.6791(27) 0.042(9) Uiso 1 d . . H41 H -0.0249(34) 0.8118(14) 0.7399(26) 0.035(9) Uiso 1 d . . H54 H -0.4453(35) 0.7958(15) 0.9410(26) 0.043(9) Uiso 1 d . . H31 H -0.1441(35) 0.9560(13) 0.7938(25) 0.036(8) Uiso 1 d . . H35 H 0.3072(40) 0.9122(16) 0.8288(30) 0.059(11) Uiso 1 d . . H15 H 0.2809(38) 0.7848(16) 1.5636(28) 0.053(10) Uiso 1 d . . H12 H 0.6351(37) 0.9441(15) 1.5535(28) 0.047(10) Uiso 1 d . . H32 H -0.0999(39) 1.0224(16) 0.6370(31) 0.060(11) Uiso 1 d . . H43 H 0.2156(39) 0.6619(17) 0.7657(32) 0.057(11) Uiso 1 d . . H33 H 0.1451(38) 1.0330(16) 0.5841(31) 0.059(11) Uiso 1 d . . H44 H 0.3265(43) 0.6937(18) 0.9508(34) 0.070(12) Uiso 1 d . . H13 H 0.6401(37) 0.8798(15) 1.7245(30) 0.049(9) Uiso 1 d . . H14 H 0.4639(36) 0.8015(15) 1.7223(30) 0.049(10) Uiso 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 0.0216(4) 0.0231(4) 0.0264(4) -0.0009(3) 0.0009(3) 0.0000(3) O1 0.0338(11) 0.0305(11) 0.0315(11) 0.0057(9) -0.0032(9) -0.0080(9) O2 0.0357(11) 0.0355(11) 0.0286(11) 0.0031(9) -0.0069(8) -0.0069(9) O3 0.0516(14) 0.0400(12) 0.0360(12) 0.0129(10) -0.0110(10) -0.0165(11) O4 0.0346(12) 0.0325(11) 0.0391(12) 0.0057(9) -0.0046(9) -0.0106(9) C10 0.0269(15) 0.028(2) 0.0272(15) -0.0010(12) 0.0008(12) 0.0034(12) C11 0.036(2) 0.031(2) 0.0249(15) -0.0007(12) -0.0020(12) 0.0059(13) C12 0.041(2) 0.042(2) 0.035(2) -0.0017(15) -0.0053(14) -0.001(2) C13 0.064(2) 0.048(2) 0.029(2) 0.000(2) -0.014(2) 0.003(2) C14 0.078(3) 0.042(2) 0.025(2) 0.004(2) -0.012(2) 0.004(2) C15 0.060(2) 0.036(2) 0.032(2) 0.0030(14) -0.002(2) -0.003(2) C16 0.035(2) 0.0279(15) 0.027(2) 0.0003(12) -0.0002(12) 0.0024(13) C17 0.030(2) 0.028(2) 0.034(2) -0.0014(13) -0.0006(12) -0.0013(13) C18 0.0246(14) 0.0251(14) 0.0274(15) 0.0020(12) 0.0000(11) 0.0023(12) C19 0.0237(14) 0.0243(14) 0.034(2) -0.0003(12) 0.0011(11) 0.0008(12) C20 0.0216(14) 0.0242(14) 0.0299(15) 0.0008(12) -0.0018(11) -0.0005(11) C30 0.0262(15) 0.0245(14) 0.0251(14) -0.0026(11) 0.0001(11) -0.0021(11) C31 0.032(2) 0.038(2) 0.030(2) 0.0014(13) 0.0022(13) 0.0039(14) C32 0.052(2) 0.042(2) 0.036(2) 0.0070(15) 0.006(2) 0.014(2) C33 0.059(2) 0.038(2) 0.035(2) 0.0090(15) 0.013(2) 0.004(2) C34 0.040(2) 0.047(2) 0.042(2) 0.003(2) 0.014(2) -0.006(2) C35 0.031(2) 0.037(2) 0.034(2) 0.0014(14) 0.0023(13) 0.0006(14) C40 0.0246(14) 0.0241(14) 0.035(2) -0.0029(12) 0.0090(12) -0.0023(12) C41 0.048(2) 0.039(2) 0.037(2) -0.008(2) 0.006(2) 0.003(2) C42 0.065(2) 0.045(2) 0.049(2) -0.017(2) 0.016(2) -0.005(2) C43 0.063(3) 0.038(2) 0.073(3) -0.018(2) 0.026(2) 0.000(2) C44 0.049(2) 0.036(2) 0.082(3) 0.002(2) 0.011(2) 0.012(2) C45 0.036(2) 0.030(2) 0.054(2) -0.0044(15) 0.002(2) 0.0053(14) C50 0.0241(13) 0.0274(14) 0.0188(13) 0.0034(11) 0.0005(10) 0.0017(12) C51 0.031(2) 0.027(2) 0.040(2) -0.0023(13) 0.0028(13) -0.0039(13) C52 0.033(2) 0.035(2) 0.037(2) -0.0003(14) 0.0063(13) 0.0044(14) C53 0.0208(15) 0.042(2) 0.031(2) 0.0077(13) 0.0008(12) 0.0026(14) C54 0.027(2) 0.036(2) 0.0251(15) 0.0038(13) -0.0044(12) -0.0049(13) C55 0.029(2) 0.029(2) 0.0210(14) -0.0018(12) -0.0001(11) -0.0013(12) _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 C20 1.735(3) . ? P1 C50 1.801(3) . ? P1 C30 1.801(3) . ? P1 C40 1.807(3) . ? O1 C10 1.211(3) . ? O2 C11 1.371(3) . ? O2 C10 1.393(3) . ? O3 C17 1.273(3) . ? O4 C19 1.334(3) . ? C10 C18 1.444(4) . ? C11 C16 1.379(4) . ? C11 C12 1.385(4) . ? C12 C13 1.382(5) . ? C13 C14 1.388(5) . ? C14 C15 1.374(5) . ? C15 C16 1.402(4) . ? C16 C17 1.456(4) . ? C17 C18 1.409(4) . ? C18 C19 1.448(4) . ? C19 C20 1.370(4) . ? C30 C31 1.389(4) . ? C30 C35 1.394(4) . ? C31 C32 1.386(4) . ? C32 C33 1.382(5) . ? C33 C34 1.378(5) . ? C34 C35 1.380(4) . ? C40 C45 1.380(4) . ? C40 C41 1.397(4) . ? C41 C42 1.374(5) . ? C42 C43 1.376(5) . ? C43 C44 1.374(6) . ? C44 C45 1.391(5) . ? C50 C51 1.384(4) . ? C50 C55 1.385(4) . ? C51 C52 1.381(4) . ? C52 C53 1.385(4) . ? C53 C54 1.372(4) . ? C54 C55 1.382(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 P1 C50 112.48(12) . . ? C20 P1 C30 107.29(13) . . ? C50 P1 C30 108.66(12) . . ? C20 P1 C40 113.74(13) . . ? C50 P1 C40 109.37(13) . . ? C30 P1 C40 104.90(13) . . ? C11 O2 C10 122.4(2) . . ? O1 C10 O2 114.5(2) . . ? O1 C10 C18 127.6(3) . . ? O2 C10 C18 117.8(2) . . ? O2 C11 C16 121.6(2) . . ? O2 C11 C12 116.4(3) . . ? C16 C11 C12 121.9(3) . . ? C13 C12 C11 118.7(3) . . ? C12 C13 C14 120.5(3) . . ? C15 C14 C13 120.2(3) . . ? C14 C15 C16 120.2(3) . . ? C11 C16 C15 118.4(3) . . ? C11 C16 C17 119.0(2) . . ? C15 C16 C17 122.6(3) . . ? O3 C17 C18 123.0(3) . . ? O3 C17 C16 118.2(3) . . ? C18 C17 C16 118.8(3) . . ? C17 C18 C10 120.3(2) . . ? C17 C18 C19 119.5(2) . . ? C10 C18 C19 120.3(2) . . ? O4 C19 C20 116.9(2) . . ? O4 C19 C18 116.3(2) . . ? C20 C19 C18 126.8(2) . . ? C19 C20 P1 119.5(2) . . ? C31 C30 C35 119.8(3) . . ? C31 C30 P1 122.5(2) . . ? C35 C30 P1 117.7(2) . . ? C32 C31 C30 119.5(3) . . ? C33 C32 C31 120.3(3) . . ? C34 C33 C32 120.3(3) . . ? C33 C34 C35 119.9(3) . . ? C34 C35 C30 120.2(3) . . ? C45 C40 C41 119.4(3) . . ? C45 C40 P1 121.6(2) . . ? C41 C40 P1 118.9(2) . . ? C42 C41 C40 120.1(3) . . ? C43 C42 C41 120.2(4) . . ? C42 C43 C44 120.2(3) . . ? C43 C44 C45 120.2(4) . . ? C40 C45 C44 119.9(3) . . ? C51 C50 C55 120.4(3) . . ? C51 C50 P1 117.7(2) . . ? C55 C50 P1 121.9(2) . . ? C52 C51 C50 120.2(3) . . ? C51 C52 C53 119.1(3) . . ? C54 C53 C52 120.6(3) . . ? C53 C54 C55 120.5(3) . . ? C54 C55 C50 119.1(3) . . ? _refine_diff_density_max 0.366 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.059 data_sso4 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H25 N2 O4 P' _chemical_formula_weight 472.46 _chemical_melting_point ? _chemical_compound_source ? 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2630(10) _cell_length_b 11.2170(10) _cell_length_c 11.8390(10) _cell_angle_alpha 77.810(10) _cell_angle_beta 89.500(10) _cell_angle_gamma 82.390(10) _cell_volume 1191.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 5 _cell_measurement_theta_max 12.5 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method ? _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Siemens P4' _diffrn_measurement_method 'Omega Scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1% _diffrn_reflns_number 4434 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4152 _reflns_number_observed 3176 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1993)' _computing_cell_refinement 'XSCANS (Fait, 1993)' _computing_data_reduction 'XSCANS (Fait, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL-PC (Sheldrick, 1995)' _computing_publication_material 'SHELXTL-PC (Sheldrick, 1995)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.6831P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4152 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_obs 0.0393 _refine_ls_wR_factor_all 0.0932 _refine_ls_wR_factor_obs 0.0835 _refine_ls_goodness_of_fit_all 1.036 _refine_ls_goodness_of_fit_obs 1.078 _refine_ls_restrained_S_all 1.036 _refine_ls_restrained_S_obs 1.078 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.21390(6) 0.72605(5) 0.87653(4) 0.01735(14) Uani 1 d . . C2 C 0.3455(3) 0.6313(2) 0.9794(2) 0.0206(5) Uani 1 d . . H2A H 0.4397(26) 0.6383(20) 0.9449(19) 0.026(6) Uiso 1 d . . H2B H 0.3233(25) 0.5492(23) 0.9840(20) 0.030(6) Uiso 1 d . . O3 O 0.3447(2) 0.77329(13) 1.10464(13) 0.0280(4) Uani 1 d . . C3 C 0.3446(2) 0.6641(2) 1.0985(2) 0.0199(5) Uani 1 d . . C4 C 0.3473(2) 0.5640(2) 1.1940(2) 0.0173(4) Uani 1 d . . O5 O 0.3190(2) 0.38144(13) 1.11331(12) 0.0251(4) Uani 1 d . . N5 N 0.3495(2) 0.3785(2) 1.30736(14) 0.0192(4) Uani 1 d . . C5 C 0.3363(2) 0.4368(2) 1.1928(2) 0.0185(4) Uani 1 d . . N6 N 0.3671(2) 0.4570(2) 1.38123(14) 0.0202(4) Uani 1 d . . C7 C 0.3645(2) 0.5662(2) 1.3131(2) 0.0183(4) Uani 1 d . . C11 C 0.0492(2) 0.7715(2) 0.9449(2) 0.0207(5) Uani 1 d . . C12 C -0.0283(3) 0.8879(2) 0.9090(2) 0.0342(6) Uani 1 d . . H12 H 0.0098(29) 0.9477(24) 0.8510(23) 0.043(8) Uiso 1 d . . C13 C -0.1633(3) 0.9165(3) 0.9557(3) 0.0443(7) Uani 1 d . . H13 H -0.2178(30) 0.9957(26) 0.9289(23) 0.048(8) Uiso 1 d . . C14 C -0.2204(3) 0.8287(3) 1.0363(2) 0.0381(6) Uani 1 d . . H14 H -0.3135(31) 0.8491(25) 1.0653(23) 0.046(8) Uiso 1 d . . C15 C -0.1430(3) 0.7132(2) 1.0735(2) 0.0333(6) Uani 1 d . . H15 H -0.1833(27) 0.6505(24) 1.1338(22) 0.039(7) Uiso 1 d . . C16 C -0.0082(3) 0.6843(2) 1.0290(2) 0.0259(5) Uani 1 d . . H16 H 0.0522(26) 0.6000(23) 1.0529(20) 0.033(7) Uiso 1 d . . C21 C 0.2892(2) 0.8551(2) 0.7924(2) 0.0201(5) Uani 1 d . . C22 C 0.3929(3) 0.9104(2) 0.8407(2) 0.0265(5) Uani 1 d . . H22 H 0.4215(25) 0.8776(21) 0.9219(21) 0.027(6) Uiso 1 d . . C23 C 0.4550(3) 1.0059(2) 0.7719(2) 0.0318(6) Uani 1 d . . H23 H 0.5342(29) 1.0414(24) 0.8038(22) 0.043(7) Uiso 1 d . . C24 C 0.4160(3) 1.0452(2) 0.6562(2) 0.0301(6) Uani 1 d . . H24 H 0.4639(29) 1.1072(25) 0.6062(23) 0.046(8) Uiso 1 d . . C25 C 0.3134(3) 0.9909(2) 0.6085(2) 0.0302(6) Uani 1 d . . H25 H 0.2853(28) 1.0167(23) 0.5303(24) 0.040(7) Uiso 1 d . . C26 C 0.2495(3) 0.8963(2) 0.6757(2) 0.0258(5) Uani 1 d . . H26 H 0.1780(25) 0.8557(21) 0.6399(19) 0.029(6) Uiso 1 d . . C31 C 0.1718(2) 0.6336(2) 0.7773(2) 0.0176(4) Uani 1 d . . C32 C 0.0309(2) 0.6101(2) 0.7597(2) 0.0229(5) Uani 1 d . . H32 H -0.0500(25) 0.6418(20) 0.8020(20) 0.026(6) Uiso 1 d . . C33 C 0.0070(3) 0.5380(2) 0.6815(2) 0.0291(5) Uani 1 d . . H33 H -0.0886(31) 0.5205(24) 0.6707(23) 0.047(8) Uiso 1 d . . C35 C 0.2610(2) 0.5152(2) 0.6381(2) 0.0229(5) Uani 1 d . . H35 H 0.3336(26) 0.4845(21) 0.5959(20) 0.027(6) Uiso 1 d . . C36 C 0.1212(3) 0.4922(2) 0.6207(2) 0.0248(5) Uani 1 d . . H36 H 0.1036(25) 0.4458(21) 0.5655(20) 0.028(6) Uiso 1 d . . C36 C 0.2870(2) 0.5858(2) 0.7161(2) 0.0221(5) Uani 1 d . . H36 H 0.3858(26) 0.6007(21) 0.7288(19) 0.028(6) Uiso 1 d . . C51 C 0.3422(3) 0.2500(2) 1.3535(2) 0.0301(6) Uani 1 d . . H51A H 0.4325(31) 0.2078(24) 1.3922(23) 0.043(8) Uiso 1 d . . H51B H 0.2607(33) 0.2386(26) 1.4073(25) 0.057(9) Uiso 1 d . . H51C H 0.3269(30) 0.2100(25) 1.2907(25) 0.049(8) Uiso 1 d . . C71 C 0.3843(3) 0.6748(2) 1.3626(2) 0.0229(5) Uani 1 d . . H71A H 0.4534(25) 0.7170(20) 1.3208(19) 0.022(6) Uiso 1 d . . H71B H 0.4217(25) 0.6480(21) 1.4391(21) 0.027(6) Uiso 1 d . . O71 O 0.2543(2) 0.8639(2) 1.3902(2) 0.0762(8) Uani 1 d . . O72 O 0.1271(2) 0.72519(15) 1.34620(15) 0.0348(4) Uani 1 d . . C72 C 0.2511(3) 0.7654(2) 1.3674(2) 0.0311(6) Uani 1 d . . C73 C -0.0044(4) 0.8084(3) 1.3516(4) 0.0531(9) Uani 1 d . . H73A H -0.0793(42) 0.7770(35) 1.3220(32) 0.088(13) Uiso 1 d . . H73B H -0.0208(40) 0.8121(33) 1.4420(35) 0.094(13) Uiso 1 d . . H73C H 0.0071(44) 0.8870(41) 1.3215(36) 0.106(15) Uiso 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 0.0201(3) 0.0174(3) 0.0146(3) -0.0028(2) 0.0010(2) -0.0034(2) C2 0.0249(13) 0.0194(11) 0.0165(11) -0.0026(9) -0.0009(9) -0.0010(9) O3 0.0419(10) 0.0182(8) 0.0233(8) -0.0032(6) -0.0001(7) -0.0034(7) C3 0.0187(11) 0.0222(12) 0.0187(11) -0.0046(9) -0.0011(9) -0.0015(9) C4 0.0168(11) 0.0201(11) 0.0157(10) -0.0050(8) -0.0001(8) -0.0029(8) O5 0.0341(9) 0.0233(8) 0.0212(8) -0.0097(6) 0.0018(7) -0.0083(7) N5 0.0215(10) 0.0176(9) 0.0186(9) -0.0032(7) 0.0023(7) -0.0038(7) C5 0.0134(11) 0.0228(11) 0.0190(11) -0.0039(9) 0.0012(8) -0.0021(9) N6 0.0212(10) 0.0232(10) 0.0167(9) -0.0053(7) 0.0014(7) -0.0032(8) C7 0.0156(11) 0.0233(11) 0.0164(10) -0.0049(9) -0.0006(8) -0.0029(9) C11 0.0228(12) 0.0223(11) 0.0184(11) -0.0084(9) 0.0003(9) -0.0016(9) C12 0.0350(15) 0.0254(13) 0.0399(15) -0.0048(11) 0.0071(12) 0.0005(11) C13 0.036(2) 0.034(2) 0.061(2) -0.0138(13) 0.0052(14) 0.0094(13) C14 0.0250(14) 0.048(2) 0.046(2) -0.0218(13) 0.0095(12) -0.0019(12) C15 0.0312(14) 0.043(2) 0.0277(13) -0.0108(11) 0.0062(11) -0.0094(12) C16 0.0262(13) 0.0275(13) 0.0236(12) -0.0054(10) 0.0034(10) -0.0025(10) C21 0.0221(12) 0.0167(10) 0.0216(11) -0.0037(8) 0.0039(9) -0.0042(9) C22 0.0330(14) 0.0260(12) 0.0213(12) -0.0047(10) 0.0002(10) -0.0072(10) C23 0.0346(14) 0.0300(13) 0.0342(14) -0.0077(11) 0.0046(11) -0.0152(11) C24 0.0383(15) 0.0204(12) 0.0311(13) -0.0023(10) 0.0088(11) -0.0075(11) C25 0.040(2) 0.0247(12) 0.0232(13) 0.0008(10) 0.0005(11) -0.0055(11) C26 0.0288(13) 0.0230(12) 0.0236(12) 0.0002(9) -0.0026(10) -0.0051(10) C31 0.0212(11) 0.0169(10) 0.0137(10) -0.0012(8) -0.0001(8) -0.0025(9) C32 0.0178(12) 0.0279(12) 0.0239(12) -0.0076(9) 0.0024(9) -0.0033(9) C33 0.0200(13) 0.0396(14) 0.0324(13) -0.0153(11) -0.0006(10) -0.0081(11) C35 0.0201(12) 0.0303(12) 0.0190(11) -0.0084(9) 0.0050(9) -0.0006(10) C36 0.0282(13) 0.0274(12) 0.0211(12) -0.0103(10) -0.0034(10) -0.0042(10) C36 0.0175(12) 0.0297(12) 0.0203(11) -0.0058(9) 0.0005(9) -0.0063(9) C51 0.038(2) 0.0196(12) 0.0294(13) 0.0009(10) 0.0064(12) -0.0038(11) C71 0.0262(13) 0.0268(12) 0.0176(11) -0.0063(9) -0.0007(10) -0.0080(10) O71 0.0499(14) 0.0504(14) 0.149(2) -0.067(2) 0.0082(14) -0.0100(11) O72 0.0283(10) 0.0271(9) 0.0499(11) -0.0125(8) -0.0002(8) 0.0003(7) C72 0.0353(14) 0.0294(13) 0.0321(13) -0.0121(10) 0.0052(11) -0.0085(11) C73 0.033(2) 0.037(2) 0.088(3) -0.017(2) 0.002(2) 0.0049(14) _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 C11 1.786(2) . ? P1 C21 1.795(2) . ? P1 C2 1.799(2) . ? P1 C31 1.799(2) . ? C2 C3 1.531(3) . ? O3 C3 1.242(2) . ? C3 C4 1.413(3) . ? C4 C7 1.426(3) . ? C4 C5 1.446(3) . ? O5 C5 1.255(2) . ? N5 C5 1.374(3) . ? N5 N6 1.390(2) . ? N5 C51 1.439(3) . ? N6 C7 1.314(3) . ? C7 C71 1.491(3) . ? C11 C12 1.387(3) . ? C11 C16 1.395(3) . ? C12 C13 1.389(4) . ? C13 C14 1.376(4) . ? C14 C15 1.381(4) . ? C15 C16 1.377(3) . ? C21 C22 1.397(3) . ? C21 C26 1.397(3) . ? C22 C23 1.389(3) . ? C23 C24 1.383(3) . ? C24 C25 1.379(3) . ? C25 C26 1.382(3) . ? C31 C32 1.392(3) . ? C31 C36 1.396(3) . ? C32 C33 1.388(3) . ? C33 C36 1.379(3) . ? C35 C36 1.379(3) . ? C35 C36 1.379(3) . ? C71 C72 1.500(3) . ? O71 C72 1.195(3) . ? O72 C72 1.333(3) . ? O72 C73 1.443(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 P1 C21 112.37(10) . . ? C11 P1 C2 111.48(10) . . ? C21 P1 C2 111.33(11) . . ? C11 P1 C31 107.99(10) . . ? C21 P1 C31 106.50(9) . . ? C2 P1 C31 106.81(10) . . ? C3 C2 P1 115.15(15) . . ? O3 C3 C4 125.3(2) . . ? O3 C3 C2 119.0(2) . . ? C4 C3 C2 115.7(2) . . ? C3 C4 C7 127.2(2) . . ? C3 C4 C5 127.9(2) . . ? C7 C4 C5 104.8(2) . . ? C5 N5 N6 113.5(2) . . ? C5 N5 C51 126.2(2) . . ? N6 N5 C51 120.2(2) . . ? O5 C5 N5 122.9(2) . . ? O5 C5 C4 133.1(2) . . ? N5 C5 C4 104.0(2) . . ? C7 N6 N5 104.9(2) . . ? N6 C7 C4 112.8(2) . . ? N6 C7 C71 120.2(2) . . ? C4 C7 C71 127.0(2) . . ? C12 C11 C16 119.8(2) . . ? C12 C11 P1 121.1(2) . . ? C16 C11 P1 118.9(2) . . ? C11 C12 C13 119.9(2) . . ? C14 C13 C12 119.8(3) . . ? C13 C14 C15 120.5(2) . . ? C16 C15 C14 120.1(2) . . ? C15 C16 C11 119.8(2) . . ? C22 C21 C26 119.7(2) . . ? C22 C21 P1 120.6(2) . . ? C26 C21 P1 119.5(2) . . ? C23 C22 C21 119.4(2) . . ? C24 C23 C22 120.4(2) . . ? C25 C24 C23 120.2(2) . . ? C24 C25 C26 120.3(2) . . ? C25 C26 C21 119.9(2) . . ? C32 C31 C36 120.1(2) . . ? C32 C31 P1 122.5(2) . . ? C36 C31 P1 117.4(2) . . ? C33 C32 C31 119.2(2) . . ? C36 C33 C32 120.3(2) . . ? C36 C35 C36 119.8(2) . . ? C33 C36 C35 120.7(2) . . ? C35 C36 C31 119.9(2) . . ? C7 C71 C72 116.7(2) . . ? C72 O72 C73 115.9(2) . . ? O71 C72 O72 122.6(2) . . ? O71 C72 C71 123.6(2) . . ? O72 C72 C71 113.8(2) . . ? _refine_diff_density_max 0.278 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.044