Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'David Fox' _publ_contact_author_address ; Department of Chemistry University of Cambridge University Chemical Laboratory Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email DJF34@CAM.AC.UK _publ_section_title ; Asymmetric synthesis of cyclopropanes and dihydrofurans based on phosphine oxide chemistry ; loop_ _publ_author_name 'David Fox' 'Sean Parris' 'Daniel Sejer Pedersen' 'Charles R. Tyzack' 'Stuart Warren' data_sw0301 _database_code_depnum_ccdc_archive 'CCDC 297304' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H25 O3 P' _chemical_formula_sum 'C29 H25 O3 P' _chemical_formula_weight 452.46 _chemical_absolute_configuration ; Flack parameter -0.02(17). ; 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 Hexagonal _symmetry_space_group_name_H-M P6(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 11.1634(1) _cell_length_b 11.1634(1) _cell_length_c 33.8352(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3651.68(7) _cell_formula_units_Z 6 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 30444 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 22.46 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1428 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Poor (weakly diffracting) crystal: theta(max)=22.5 degrees. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 16946 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 22.47 _reflns_number_total 3114 _reflns_number_gt 2678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0792P)^2^+1.9286P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(17) _refine_ls_number_reflns 3114 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1514 _refine_ls_wR_factor_gt 0.1422 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.010 _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 0.91648(14) 0.51850(13) 0.09638(4) 0.0664(4) Uani 1 1 d . . . O1 O 0.6298(4) 0.2248(4) 0.02832(12) 0.0920(11) Uani 1 1 d . . . C1 C 0.7593(6) 0.3272(5) 0.03811(16) 0.0760(14) Uani 1 1 d . . . O2 O 0.9899(4) 0.4636(4) 0.11993(11) 0.0931(12) Uani 1 1 d . . . C2 C 0.7663(5) 0.3903(5) 0.07294(14) 0.0691(13) Uani 1 1 d . . . O3 O 0.5385(5) 0.4128(4) 0.02192(13) 0.1096(14) Uani 1 1 d . . . H3 H 0.5123 0.4286 0.0003 0.164 Uiso 1 1 calc R . . C3 C 0.6210(5) 0.3262(6) 0.08996(15) 0.0779(15) Uani 1 1 d . . . H3A H 0.5955 0.3976 0.0956 0.094 Uiso 1 1 calc R . . H3B H 0.6123 0.2741 0.1145 0.094 Uiso 1 1 calc R . . C4 C 0.5313(5) 0.2289(5) 0.05663(17) 0.0769(14) Uani 1 1 d . . . H4 H 0.4705 0.1341 0.0676 0.092 Uiso 1 1 calc R . . C6 C 0.8650(6) 0.3458(5) 0.00908(17) 0.0796(16) Uani 1 1 d . . . C7 C 0.9878(6) 0.3561(5) 0.0214(2) 0.0892(17) Uani 1 1 d . . . H7 H 1.0062 0.3527 0.0486 0.107 Uiso 1 1 calc R . . C8 C 1.0840(7) 0.3715(6) -0.0074(3) 0.105(2) Uani 1 1 d . . . H8 H 1.1679 0.3767 0.0008 0.126 Uiso 1 1 calc R . . C9 C 1.0630(10) 0.3793(6) -0.0461(3) 0.122(3) Uani 1 1 d . . . H9 H 1.1295 0.3882 -0.0651 0.147 Uiso 1 1 calc R . . C10 C 0.9461(9) 0.3743(7) -0.0570(2) 0.116(2) Uani 1 1 d . . . H10 H 0.9316 0.3835 -0.0842 0.139 Uiso 1 1 calc R . . C11 C 0.8457(7) 0.3564(7) -0.03052(19) 0.1019(19) Uani 1 1 d . . . H11 H 0.7628 0.3514 -0.0396 0.122 Uiso 1 1 calc R . . C12 C 1.0253(6) 0.6395(5) 0.05849(18) 0.0825(16) Uani 1 1 d . . . C13 C 1.1637(7) 0.6966(8) 0.0601(3) 0.128(3) Uani 1 1 d . . . H13 H 1.2070 0.6741 0.0807 0.153 Uiso 1 1 calc R . . C14 C 1.2487(9) 0.7991(9) 0.0274(4) 0.139(3) Uani 1 1 d . . . H14 H 1.3468 0.8460 0.0265 0.167 Uiso 1 1 calc R . . C15 C 1.1704(14) 0.8164(9) 0.0001(3) 0.135(3) Uani 1 1 d . . . H15 H 1.2215 0.8774 -0.0208 0.162 Uiso 1 1 calc R . . C16 C 1.0402(12) 0.7651(8) -0.0024(3) 0.133(3) Uani 1 1 d . . . H16 H 0.9975 0.7871 -0.0232 0.159 Uiso 1 1 calc R . . C17 C 0.9672(8) 0.6757(6) 0.02734(18) 0.099(2) Uani 1 1 d . . . H17 H 0.8694 0.6349 0.0269 0.119 Uiso 1 1 calc R . . C18 C 0.8642(5) 0.6169(5) 0.12709(15) 0.0682(13) Uani 1 1 d . . . C19 C 0.7877(11) 0.6732(10) 0.1121(2) 0.141(4) Uani 1 1 d . . . H19 H 0.7582 0.6575 0.0853 0.169 Uiso 1 1 calc R . . C20 C 0.7541(12) 0.7532(12) 0.1364(3) 0.170(4) Uani 1 1 d . . . H20 H 0.6985 0.7888 0.1264 0.204 Uiso 1 1 calc R . . C21 C 0.7999(10) 0.7797(10) 0.1734(3) 0.134(3) Uani 1 1 d . . . H21 H 0.7856 0.8424 0.1890 0.161 Uiso 1 1 calc R . . C22 C 0.8660(10) 0.7183(12) 0.1890(3) 0.163(4) Uani 1 1 d . . . H22 H 0.8898 0.7297 0.2163 0.196 Uiso 1 1 calc R . . C23 C 0.8995(8) 0.6385(9) 0.1653(2) 0.120(3) Uani 1 1 d . . . H23 H 0.9489 0.5978 0.1765 0.144 Uiso 1 1 calc R . . C24 C 0.4440(6) 0.2741(5) 0.03412(16) 0.0773(14) Uani 1 1 d . . . H24 H 0.4069 0.2151 0.0100 0.093 Uiso 1 1 calc R . . C25 C 0.3273(6) 0.2599(6) 0.05743(16) 0.0772(14) Uani 1 1 d . . . C26 C 0.3311(8) 0.3756(7) 0.07462(18) 0.0987(18) Uani 1 1 d . . . H26 H 0.4101 0.4646 0.0711 0.118 Uiso 1 1 calc R . . C27 C 0.2247(9) 0.3619(11) 0.0959(3) 0.128(3) Uani 1 1 d . . . H27 H 0.2288 0.4427 0.1064 0.153 Uiso 1 1 calc R . . C28 C 0.1158(8) 0.2433(10) 0.1028(2) 0.107(2) Uani 1 1 d . . . H28 H 0.0459 0.2388 0.1198 0.129 Uiso 1 1 calc R . . C29 C 0.0985(8) 0.1179(11) 0.0854(3) 0.142(3) Uani 1 1 d . . . H29 H 0.0162 0.0314 0.0887 0.170 Uiso 1 1 calc R . . C30 C 0.2137(6) 0.1321(9) 0.06252(19) 0.103(2) Uani 1 1 d . . . H30 H 0.2107 0.0529 0.0511 0.124 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 0.0818(9) 0.0760(8) 0.0610(7) 0.0033(6) 0.0078(6) 0.0541(7) O1 0.087(3) 0.091(3) 0.090(2) -0.013(2) 0.025(2) 0.039(2) C1 0.080(4) 0.077(3) 0.077(4) 0.003(3) 0.014(3) 0.044(3) O2 0.128(3) 0.115(3) 0.086(2) -0.013(2) -0.017(2) 0.098(3) C2 0.083(3) 0.084(3) 0.053(3) 0.011(3) 0.017(2) 0.051(3) O3 0.143(4) 0.078(3) 0.093(3) 0.006(2) -0.019(3) 0.043(2) C3 0.085(4) 0.098(4) 0.060(3) 0.008(3) 0.018(3) 0.053(3) C4 0.077(3) 0.073(3) 0.081(3) 0.007(3) 0.028(3) 0.038(3) C6 0.089(4) 0.067(3) 0.086(4) -0.002(3) 0.033(3) 0.041(3) C7 0.090(4) 0.068(3) 0.110(5) -0.017(3) 0.022(4) 0.041(3) C8 0.085(4) 0.087(4) 0.141(7) -0.027(4) 0.024(4) 0.041(3) C9 0.125(6) 0.075(4) 0.148(8) 0.000(4) 0.082(6) 0.036(4) C10 0.141(6) 0.110(5) 0.090(5) 0.011(4) 0.058(5) 0.057(5) C11 0.116(5) 0.111(5) 0.084(5) 0.005(4) 0.027(4) 0.062(4) C12 0.088(4) 0.069(3) 0.089(4) -0.015(3) 0.023(3) 0.038(3) C13 0.092(5) 0.129(6) 0.147(7) -0.031(5) 0.030(5) 0.044(4) C14 0.081(5) 0.126(6) 0.176(9) -0.061(6) 0.035(6) 0.025(4) C15 0.140(8) 0.103(6) 0.157(9) -0.020(6) 0.033(7) 0.057(6) C16 0.162(8) 0.115(6) 0.125(7) 0.020(5) 0.049(6) 0.072(6) C17 0.145(6) 0.094(4) 0.070(4) 0.025(3) 0.041(4) 0.068(4) C18 0.082(3) 0.080(3) 0.060(3) 0.003(2) 0.012(2) 0.054(3) C19 0.257(10) 0.212(9) 0.073(4) 0.033(5) 0.041(5) 0.206(9) C20 0.287(12) 0.252(11) 0.108(7) 0.029(7) 0.052(8) 0.237(11) C21 0.161(7) 0.168(7) 0.127(7) -0.037(6) 0.013(6) 0.123(7) C22 0.184(8) 0.290(12) 0.115(6) -0.071(7) -0.040(6) 0.193(10) C23 0.146(6) 0.200(8) 0.089(5) -0.037(5) -0.015(4) 0.145(6) C24 0.104(4) 0.062(3) 0.071(3) 0.001(2) 0.001(3) 0.046(3) C25 0.083(4) 0.087(4) 0.078(4) -0.015(3) -0.006(3) 0.054(3) C26 0.127(5) 0.109(5) 0.088(4) -0.004(4) 0.005(4) 0.080(4) C27 0.121(6) 0.171(8) 0.109(6) 0.036(6) 0.031(5) 0.087(6) C28 0.106(5) 0.150(6) 0.099(5) -0.021(5) 0.019(4) 0.089(5) C29 0.086(5) 0.196(9) 0.126(6) 0.000(6) -0.012(4) 0.057(5) C30 0.081(4) 0.165(7) 0.088(4) -0.018(4) 0.005(3) 0.079(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O2 1.478(4) . ? P1 C2 1.758(5) . ? P1 C18 1.807(5) . ? P1 C12 1.817(6) . ? O1 C1 1.362(6) . ? O1 C4 1.476(6) . ? C1 C2 1.355(7) . ? C1 C6 1.468(7) . ? C2 C3 1.521(7) . ? O3 C24 1.431(7) . ? C3 C4 1.538(8) . ? C4 C24 1.509(8) . ? C6 C11 1.372(8) . ? C6 C7 1.381(8) . ? C7 C8 1.393(9) . ? C8 C9 1.342(12) . ? C9 C10 1.330(11) . ? C10 C11 1.368(9) . ? C12 C13 1.346(9) . ? C12 C17 1.399(9) . ? C13 C14 1.531(13) . ? C14 C15 1.351(14) . ? C15 C16 1.271(12) . ? C16 C17 1.364(9) . ? C18 C23 1.339(8) . ? C18 C19 1.385(8) . ? C19 C20 1.395(10) . ? C20 C21 1.331(12) . ? C21 C22 1.341(12) . ? C22 C23 1.381(9) . ? C24 C25 1.463(8) . ? C25 C30 1.365(9) . ? C25 C26 1.398(8) . ? C26 C27 1.330(9) . ? C27 C28 1.295(10) . ? C28 C29 1.440(11) . ? C29 C30 1.440(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 P1 C2 114.0(2) . . ? O2 P1 C18 110.9(2) . . ? C2 P1 C18 106.7(2) . . ? O2 P1 C12 112.7(3) . . ? C2 P1 C12 107.3(3) . . ? C18 P1 C12 104.6(2) . . ? C1 O1 C4 108.1(4) . . ? C2 C1 O1 114.1(5) . . ? C2 C1 C6 132.5(5) . . ? O1 C1 C6 113.4(5) . . ? C1 C2 C3 108.3(5) . . ? C1 C2 P1 126.8(4) . . ? C3 C2 P1 124.8(4) . . ? C2 C3 C4 102.7(4) . . ? O1 C4 C24 107.4(4) . . ? O1 C4 C3 105.4(4) . . ? C24 C4 C3 115.8(4) . . ? C11 C6 C7 118.6(6) . . ? C11 C6 C1 121.1(6) . . ? C7 C6 C1 120.3(6) . . ? C6 C7 C8 118.1(7) . . ? C9 C8 C7 122.7(7) . . ? C10 C9 C8 117.8(6) . . ? C9 C10 C11 122.7(8) . . ? C10 C11 C6 119.9(7) . . ? C13 C12 C17 118.8(7) . . ? C13 C12 P1 120.4(6) . . ? C17 C12 P1 120.8(5) . . ? C12 C13 C14 117.4(9) . . ? C15 C14 C13 113.4(8) . . ? C16 C15 C14 131.1(11) . . ? C15 C16 C17 114.2(10) . . ? C16 C17 C12 125.0(8) . . ? C23 C18 C19 117.7(5) . . ? C23 C18 P1 120.7(4) . . ? C19 C18 P1 121.7(4) . . ? C18 C19 C20 120.0(7) . . ? C21 C20 C19 120.0(8) . . ? C20 C21 C22 120.4(7) . . ? C21 C22 C23 119.8(8) . . ? C18 C23 C22 121.8(6) . . ? O3 C24 C25 114.1(4) . . ? O3 C24 C4 104.9(4) . . ? C25 C24 C4 112.4(4) . . ? C30 C25 C26 119.8(6) . . ? C30 C25 C24 119.5(5) . . ? C26 C25 C24 120.7(5) . . ? C27 C26 C25 120.4(8) . . ? C28 C27 C26 122.9(9) . . ? C27 C28 C29 121.4(7) . . ? C30 C29 C28 115.8(7) . . ? C25 C30 C29 119.6(7) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 22.47 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.278 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.038 # Attachment 'paper 2 compound 39.cif' data_sw0302 _database_code_depnum_ccdc_archive 'CCDC 297305' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H27 O3 P' _chemical_formula_sum 'C29 H27 O3 P' _chemical_formula_weight 454.48 _chemical_absolute_configuration ; Flack parameter -0.02(13). ; 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 5.9419(1) _cell_length_b 14.3610(3) _cell_length_c 26.6529(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2274.34(9) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 75668 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 22.46 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.710 _exptl_absorpt_correction_T_max 1.005 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Poor (weakly diffracting) crystal. Theta(max) = 22.5 degrees. The -OH hydrogen atom on O3 was not located reliably but placed in a reasonable position with SHELX. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 14297 _diffrn_reflns_av_R_equivalents 0.0953 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 22.49 _reflns_number_total 2966 _reflns_number_gt 2628 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0621P)^2^+0.3683P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(13) _refine_ls_number_reflns 2966 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.59658(13) 0.64320(5) 0.34358(3) 0.0323(3) Uani 1 1 d . . . O1 O 0.6816(4) 0.41314(14) 0.35902(8) 0.0385(6) Uani 1 1 d . . . C1 C 0.8405(5) 0.4732(2) 0.33507(12) 0.0324(8) Uani 1 1 d . . . H1 H 0.9943 0.4474 0.3414 0.039 Uiso 1 1 calc R . . O2 O 0.3699(3) 0.59908(14) 0.34268(9) 0.0375(6) Uani 1 1 d . . . C2 C 0.8199(5) 0.5662(2) 0.36440(12) 0.0320(8) Uani 1 1 d . . . H2 H 0.9670 0.6000 0.3633 0.038 Uiso 1 1 calc R . . O3 O 0.3004(4) 0.47905(19) 0.42214(10) 0.0566(8) Uani 1 1 d . . . H3C H 0.3424 0.5101 0.3971 0.085 Uiso 1 1 calc R . . C3 C 0.7755(6) 0.5307(2) 0.41878(13) 0.0348(8) Uani 1 1 d . . . H3A H 0.9152 0.5328 0.4390 0.042 Uiso 1 1 calc R . . H3B H 0.6594 0.5693 0.4355 0.042 Uiso 1 1 calc R . . C4 C 0.6927(6) 0.4290(2) 0.41246(13) 0.0348(8) Uani 1 1 d . . . H4 H 0.8044 0.3854 0.4278 0.042 Uiso 1 1 calc R . . C6 C 0.7994(6) 0.4708(2) 0.27911(12) 0.0322(8) Uani 1 1 d . . . C7 C 0.5984(6) 0.4405(2) 0.25957(13) 0.0379(8) Uani 1 1 d . . . H7 H 0.4780 0.4254 0.2816 0.045 Uiso 1 1 calc R . . C8 C 0.5687(7) 0.4315(2) 0.20811(14) 0.0455(10) Uani 1 1 d . . . H8 H 0.4298 0.4095 0.1951 0.055 Uiso 1 1 calc R . . C9 C 0.7426(7) 0.4548(2) 0.17590(15) 0.0518(11) Uani 1 1 d . . . H9 H 0.7238 0.4489 0.1407 0.062 Uiso 1 1 calc R . . C10 C 0.9432(7) 0.4867(3) 0.19535(14) 0.0484(10) Uani 1 1 d . . . H10 H 1.0624 0.5033 0.1734 0.058 Uiso 1 1 calc R . . C11 C 0.9724(6) 0.4946(2) 0.24693(14) 0.0407(9) Uani 1 1 d . . . H11 H 1.1114 0.5163 0.2601 0.049 Uiso 1 1 calc R . . C12 C 0.6769(5) 0.6884(2) 0.28286(12) 0.0316(8) Uani 1 1 d . . . C13 C 0.5191(6) 0.6852(2) 0.24514(13) 0.0377(8) Uani 1 1 d . . . H13 H 0.3745 0.6595 0.2514 0.045 Uiso 1 1 calc R . . C14 C 0.5715(6) 0.7198(2) 0.19760(13) 0.0431(9) Uani 1 1 d . . . H14 H 0.4620 0.7178 0.1716 0.052 Uiso 1 1 calc R . . C15 C 0.7789(6) 0.7563(2) 0.18829(14) 0.0417(9) Uani 1 1 d . . . H15 H 0.8124 0.7805 0.1560 0.050 Uiso 1 1 calc R . . C16 C 0.9408(6) 0.7585(2) 0.22544(14) 0.0396(9) Uani 1 1 d . . . H16 H 1.0856 0.7835 0.2186 0.048 Uiso 1 1 calc R . . C17 C 0.8910(6) 0.7240(2) 0.27273(13) 0.0361(8) Uani 1 1 d . . . H17 H 1.0025 0.7245 0.2983 0.043 Uiso 1 1 calc R . . C18 C 0.6043(5) 0.7383(2) 0.38860(13) 0.0356(8) Uani 1 1 d . . . C19 C 0.4287(6) 0.7466(3) 0.42195(15) 0.0520(10) Uani 1 1 d . . . H19 H 0.3055 0.7045 0.4201 0.062 Uiso 1 1 calc R . . C20 C 0.4303(8) 0.8160(3) 0.45834(17) 0.0667(13) Uani 1 1 d . . . H20 H 0.3075 0.8217 0.4810 0.080 Uiso 1 1 calc R . . C21 C 0.6094(8) 0.8768(3) 0.46172(16) 0.0594(11) Uani 1 1 d . . . H21 H 0.6113 0.9236 0.4869 0.071 Uiso 1 1 calc R . . C22 C 0.7840(7) 0.8692(3) 0.42871(16) 0.0580(11) Uani 1 1 d . . . H22 H 0.9066 0.9115 0.4306 0.070 Uiso 1 1 calc R . . C23 C 0.7826(6) 0.7998(2) 0.39241(15) 0.0514(10) Uani 1 1 d . . . H23 H 0.9058 0.7945 0.3699 0.062 Uiso 1 1 calc R . . C24 C 0.4601(6) 0.4071(2) 0.43208(13) 0.0394(9) Uani 1 1 d . . . H24 H 0.4068 0.3497 0.4144 0.047 Uiso 1 1 calc R . . C25 C 0.4470(5) 0.3881(2) 0.48815(13) 0.0358(8) Uani 1 1 d . . . C26 C 0.2517(6) 0.3480(2) 0.50644(14) 0.0428(9) Uani 1 1 d . . . H26 H 0.1338 0.3325 0.4839 0.051 Uiso 1 1 calc R . . C27 C 0.2258(7) 0.3301(3) 0.55765(15) 0.0511(10) Uani 1 1 d . . . H27 H 0.0892 0.3044 0.5700 0.061 Uiso 1 1 calc R . . C28 C 0.3989(7) 0.3499(3) 0.59004(14) 0.0502(9) Uani 1 1 d . . . H28 H 0.3823 0.3374 0.6248 0.060 Uiso 1 1 calc R . . C29 C 0.5954(7) 0.3874(2) 0.57243(14) 0.0487(10) Uani 1 1 d . . . H29 H 0.7156 0.4001 0.5949 0.058 Uiso 1 1 calc R . . C30 C 0.6191(6) 0.4072(2) 0.52102(14) 0.0422(9) Uani 1 1 d . . . H30 H 0.7549 0.4340 0.5089 0.051 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 0.0343(5) 0.0294(5) 0.0331(5) 0.0011(4) -0.0008(4) 0.0006(4) O1 0.0547(14) 0.0314(11) 0.0294(15) -0.0022(10) -0.0013(11) -0.0043(11) C1 0.0343(17) 0.0320(17) 0.031(2) 0.0008(15) -0.0006(16) 0.0011(14) O2 0.0340(12) 0.0391(12) 0.0395(14) 0.0056(11) -0.0024(12) 0.0023(9) C2 0.0336(17) 0.0285(16) 0.0339(19) -0.0012(15) -0.0037(15) 0.0005(14) O3 0.0447(14) 0.0733(18) 0.0517(18) 0.0255(14) -0.0007(13) 0.0059(13) C3 0.0381(19) 0.0350(18) 0.031(2) -0.0015(15) -0.0043(16) 0.0043(15) C4 0.044(2) 0.0294(17) 0.031(2) 0.0014(15) -0.0071(16) 0.0032(15) C6 0.043(2) 0.0221(16) 0.032(2) -0.0001(14) 0.0003(18) 0.0025(14) C7 0.045(2) 0.0302(17) 0.038(2) 0.0016(16) -0.0017(17) 0.0006(17) C8 0.059(2) 0.035(2) 0.043(2) -0.0044(17) -0.010(2) -0.0050(18) C9 0.081(3) 0.040(2) 0.034(2) -0.0035(17) -0.003(2) 0.002(2) C10 0.065(3) 0.040(2) 0.041(3) 0.0039(17) 0.014(2) 0.0042(19) C11 0.049(2) 0.0290(19) 0.044(2) -0.0016(17) 0.0043(18) 0.0023(15) C12 0.0377(19) 0.0237(16) 0.033(2) -0.0025(14) 0.0002(17) 0.0029(14) C13 0.0394(19) 0.0334(18) 0.040(2) 0.0018(16) 0.0003(17) 0.0012(15) C14 0.047(2) 0.046(2) 0.037(2) -0.0004(17) -0.0035(17) 0.0031(17) C15 0.052(2) 0.037(2) 0.036(2) 0.0053(16) 0.0060(18) 0.0067(18) C16 0.047(2) 0.0257(17) 0.046(2) 0.0001(16) 0.0091(19) -0.0010(15) C17 0.0396(19) 0.0324(17) 0.036(2) -0.0023(16) 0.0029(17) 0.0028(15) C18 0.0422(18) 0.0284(17) 0.036(2) 0.0033(15) 0.0018(18) 0.0050(16) C19 0.050(2) 0.048(2) 0.058(3) -0.010(2) 0.007(2) 0.0000(19) C20 0.074(3) 0.068(3) 0.059(3) -0.022(2) 0.025(2) 0.009(3) C21 0.085(3) 0.044(2) 0.049(3) -0.0139(18) 0.012(2) 0.002(2) C22 0.078(3) 0.042(2) 0.054(3) -0.009(2) 0.008(2) -0.013(2) C23 0.062(2) 0.046(2) 0.047(3) -0.0104(19) 0.010(2) -0.0108(19) C24 0.047(2) 0.039(2) 0.032(2) 0.0042(16) -0.0049(17) -0.0010(16) C25 0.044(2) 0.0316(17) 0.032(2) 0.0024(15) -0.0035(17) 0.0048(15) C26 0.044(2) 0.046(2) 0.039(2) 0.0038(18) -0.0037(16) -0.0019(17) C27 0.054(2) 0.051(2) 0.048(3) 0.0101(19) 0.005(2) 0.0014(18) C28 0.063(2) 0.054(2) 0.034(2) 0.0063(18) 0.003(2) 0.005(2) C29 0.061(2) 0.050(2) 0.035(2) -0.0017(17) -0.007(2) -0.001(2) C30 0.046(2) 0.0408(19) 0.040(2) 0.0001(16) -0.0005(18) -0.0015(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O2 1.489(2) . ? P1 C12 1.808(3) . ? P1 C2 1.815(3) . ? P1 C18 1.819(3) . ? O1 C1 1.429(4) . ? O1 C4 1.444(4) . ? C1 C6 1.512(5) . ? C1 C2 1.552(4) . ? C1 H1 1.0000 . ? C2 C3 1.558(5) . ? C2 H2 1.0000 . ? O3 C24 1.428(4) . ? O3 H3C 0.8400 . ? C3 C4 1.550(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C24 1.511(5) . ? C4 H4 1.0000 . ? C6 C7 1.374(5) . ? C6 C11 1.381(5) . ? C7 C8 1.389(5) . ? C7 H7 0.9500 . ? C8 C9 1.384(5) . ? C8 H8 0.9500 . ? C9 C10 1.378(5) . ? C9 H9 0.9500 . ? C10 C11 1.390(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.376(5) . ? C12 C17 1.397(5) . ? C13 C14 1.396(5) . ? C13 H13 0.9500 . ? C14 C15 1.363(5) . ? C14 H14 0.9500 . ? C15 C16 1.381(5) . ? C15 H15 0.9500 . ? C16 C17 1.387(5) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.376(5) . ? C18 C23 1.383(5) . ? C19 C20 1.391(6) . ? C19 H19 0.9500 . ? C20 C21 1.379(6) . ? C20 H20 0.9500 . ? C21 C22 1.364(6) . ? C21 H21 0.9500 . ? C22 C23 1.389(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.521(5) . ? C24 H24 1.0000 . ? C25 C30 1.374(5) . ? C25 C26 1.384(5) . ? C26 C27 1.398(5) . ? C26 H26 0.9500 . ? C27 C28 1.372(5) . ? C27 H27 0.9500 . ? C28 C29 1.369(5) . ? C28 H28 0.9500 . ? C29 C30 1.406(5) . ? C29 H29 0.9500 . ? C30 H30 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 O2 P1 C12 112.16(15) . . ? O2 P1 C2 114.02(13) . . ? C12 P1 C2 107.44(15) . . ? O2 P1 C18 110.67(14) . . ? C12 P1 C18 108.33(15) . . ? C2 P1 C18 103.75(15) . . ? C1 O1 C4 108.4(2) . . ? O1 C1 C6 108.7(2) . . ? O1 C1 C2 104.0(2) . . ? C6 C1 C2 120.2(3) . . ? O1 C1 H1 107.8 . . ? C6 C1 H1 107.8 . . ? C2 C1 H1 107.8 . . ? C1 C2 C3 101.6(2) . . ? C1 C2 P1 115.3(2) . . ? C3 C2 P1 111.1(2) . . ? C1 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? P1 C2 H2 109.5 . . ? C24 O3 H3C 109.5 . . ? C4 C3 C2 105.1(3) . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3B 110.7 . . ? C2 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? O1 C4 C24 105.5(3) . . ? O1 C4 C3 105.7(3) . . ? C24 C4 C3 116.7(3) . . ? O1 C4 H4 109.6 . . ? C24 C4 H4 109.6 . . ? C3 C4 H4 109.6 . . ? C7 C6 C11 119.3(3) . . ? C7 C6 C1 121.4(3) . . ? C11 C6 C1 119.1(3) . . ? C6 C7 C8 120.9(3) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 119.7(4) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 119.5(4) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.5(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C6 C11 C10 120.1(4) . . ? C6 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C17 119.4(3) . . ? C13 C12 P1 117.5(2) . . ? C17 C12 P1 123.0(3) . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C17 119.7(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C12 120.1(3) . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? C19 C18 C23 118.6(3) . . ? C19 C18 P1 118.2(3) . . ? C23 C18 P1 123.2(3) . . ? C18 C19 C20 120.5(3) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C21 C20 C19 120.3(4) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 119.6(4) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C23 120.1(4) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C18 C23 C22 120.9(4) . . ? C18 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? O3 C24 C4 113.1(3) . . ? O3 C24 C25 106.2(3) . . ? C4 C24 C25 115.1(3) . . ? O3 C24 H24 107.4 . . ? C4 C24 H24 107.4 . . ? C25 C24 H24 107.4 . . ? C30 C25 C26 118.8(3) . . ? C30 C25 C24 123.5(3) . . ? C26 C25 C24 117.6(3) . . ? C25 C26 C27 120.9(3) . . ? C25 C26 H26 119.6 . . ? C27 C26 H26 119.6 . . ? C28 C27 C26 119.6(4) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C29 C28 C27 120.3(4) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C28 C29 C30 119.9(4) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C25 C30 C29 120.4(3) . . ? C25 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? 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 C4 O1 C1 C6 -169.2(2) . . . . ? C4 O1 C1 C2 -40.0(3) . . . . ? O1 C1 C2 C3 35.6(3) . . . . ? C6 C1 C2 C3 157.5(3) . . . . ? O1 C1 C2 P1 -84.6(3) . . . . ? C6 C1 C2 P1 37.2(4) . . . . ? O2 P1 C2 C1 54.7(3) . . . . ? C12 P1 C2 C1 -70.3(2) . . . . ? C18 P1 C2 C1 175.1(2) . . . . ? O2 P1 C2 C3 -60.2(2) . . . . ? C12 P1 C2 C3 174.8(2) . . . . ? C18 P1 C2 C3 60.3(2) . . . . ? C1 C2 C3 C4 -19.4(3) . . . . ? P1 C2 C3 C4 103.8(2) . . . . ? C1 O1 C4 C24 151.1(2) . . . . ? C1 O1 C4 C3 26.9(3) . . . . ? C2 C3 C4 O1 -2.9(3) . . . . ? C2 C3 C4 C24 -119.7(3) . . . . ? O1 C1 C6 C7 19.1(4) . . . . ? C2 C1 C6 C7 -100.4(3) . . . . ? O1 C1 C6 C11 -157.0(3) . . . . ? C2 C1 C6 C11 83.5(4) . . . . ? C11 C6 C7 C8 1.3(5) . . . . ? C1 C6 C7 C8 -174.8(3) . . . . ? C6 C7 C8 C9 -1.0(5) . . . . ? C7 C8 C9 C10 0.0(5) . . . . ? C8 C9 C10 C11 0.7(5) . . . . ? C7 C6 C11 C10 -0.7(5) . . . . ? C1 C6 C11 C10 175.5(3) . . . . ? C9 C10 C11 C6 -0.3(5) . . . . ? O2 P1 C12 C13 5.7(3) . . . . ? C2 P1 C12 C13 131.7(2) . . . . ? C18 P1 C12 C13 -116.8(2) . . . . ? O2 P1 C12 C17 -172.9(2) . . . . ? C2 P1 C12 C17 -46.9(3) . . . . ? C18 P1 C12 C17 64.6(3) . . . . ? C17 C12 C13 C14 -1.8(5) . . . . ? P1 C12 C13 C14 179.5(3) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C13 C14 C15 C16 0.9(5) . . . . ? C14 C15 C16 C17 -0.6(5) . . . . ? C15 C16 C17 C12 -0.9(5) . . . . ? C13 C12 C17 C16 2.1(4) . . . . ? P1 C12 C17 C16 -179.3(2) . . . . ? O2 P1 C18 C19 12.4(3) . . . . ? C12 P1 C18 C19 135.7(3) . . . . ? C2 P1 C18 C19 -110.3(3) . . . . ? O2 P1 C18 C23 -170.7(3) . . . . ? C12 P1 C18 C23 -47.4(3) . . . . ? C2 P1 C18 C23 66.6(3) . . . . ? C23 C18 C19 C20 0.6(6) . . . . ? P1 C18 C19 C20 177.7(3) . . . . ? C18 C19 C20 C21 -0.7(6) . . . . ? C19 C20 C21 C22 0.9(7) . . . . ? C20 C21 C22 C23 -1.0(7) . . . . ? C19 C18 C23 C22 -0.7(5) . . . . ? P1 C18 C23 C22 -177.6(3) . . . . ? C21 C22 C23 C18 0.9(6) . . . . ? O1 C4 C24 O3 -76.7(3) . . . . ? C3 C4 C24 O3 40.2(4) . . . . ? O1 C4 C24 C25 161.0(3) . . . . ? C3 C4 C24 C25 -82.0(4) . . . . ? O3 C24 C25 C30 -113.1(3) . . . . ? C4 C24 C25 C30 12.8(5) . . . . ? O3 C24 C25 C26 67.9(4) . . . . ? C4 C24 C25 C26 -166.1(3) . . . . ? C30 C25 C26 C27 2.2(5) . . . . ? C24 C25 C26 C27 -178.8(3) . . . . ? C25 C26 C27 C28 -2.0(6) . . . . ? C26 C27 C28 C29 0.4(6) . . . . ? C27 C28 C29 C30 1.0(6) . . . . ? C26 C25 C30 C29 -0.8(5) . . . . ? C24 C25 C30 C29 -179.8(3) . . . . ? C28 C29 C30 C25 -0.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.328 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.086 # Attachment 'paper 2 compound 25.cif' data_sw0501 _database_code_depnum_ccdc_archive 'CCDC 297306' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H24 N3 O2 P' _chemical_formula_sum 'C29 H24 N3 O2 P' _chemical_formula_weight 477.48 _chemical_absolute_configuration ; Flack parameter 0.01(13) ; 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.4713(3) _cell_length_b 8.5479(3) _cell_length_c 17.4621(6) _cell_angle_alpha 83.267(2) _cell_angle_beta 83.693(2) _cell_angle_gamma 74.518(2) _cell_volume 1206.09(7) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 14018 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_T_max 1.003 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 12870 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0950 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.55 _reflns_number_total 8246 _reflns_number_gt 6485 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0783P)^2^+1.0712P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(13) _refine_ls_number_reflns 8246 _refine_ls_number_parameters 631 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1860 _refine_ls_wR_factor_gt 0.1647 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1_1 P -0.02607(14) 0.46372(15) 0.16577(7) 0.0266(3) Uani 1 1 d . . . O1_1 O 0.1103(5) 0.3454(4) 0.3833(2) 0.0372(9) Uani 1 1 d . . . O2_1 O 0.0959(5) 0.3573(5) 0.1133(2) 0.0339(8) Uani 1 1 d . . . N1_1 N 0.2067(6) 0.6359(6) 0.3985(3) 0.0455(13) Uani 1 1 d . . . N2_1 N 0.3404(7) 0.5401(7) 0.4113(3) 0.0460(13) Uani 1 1 d . . . N3_1 N 0.4684(8) 0.4636(9) 0.4159(4) 0.0718(19) Uani 1 1 d . . . C1_1 C 0.1086(6) 0.3135(6) 0.3076(3) 0.0283(11) Uani 1 1 d . . . C2_1 C 0.0123(6) 0.4381(6) 0.2658(3) 0.0292(11) Uani 1 1 d . . . C3_1 C -0.0614(8) 0.5761(7) 0.3170(3) 0.0382(13) Uani 1 1 d . . . H3A_1 H -0.1823 0.6127 0.3159 0.046 Uiso 1 1 calc R . . H3B_1 H -0.0140 0.6702 0.3011 0.046 Uiso 1 1 calc R . . C4_1 C -0.0123(7) 0.4964(7) 0.3969(3) 0.0348(12) Uani 1 1 d . . . H4_1 H -0.1104 0.4708 0.4277 0.042 Uiso 1 1 calc R . . C5_1 C 0.0591(7) 0.6003(7) 0.4425(3) 0.0345(12) Uani 1 1 d . . . H5_1 H 0.0878 0.5419 0.4942 0.041 Uiso 1 1 calc R . . C6_1 C -0.0694(7) 0.7609(6) 0.4527(3) 0.0312(12) Uani 1 1 d . . . C7_1 C -0.0551(8) 0.9048(7) 0.4102(3) 0.0395(13) Uani 1 1 d . . . H7_1 H 0.0396 0.9072 0.3759 0.047 Uiso 1 1 calc R . . C8_1 C -0.1831(9) 1.0469(8) 0.4186(4) 0.0490(16) Uani 1 1 d . . . H8_1 H -0.1744 1.1461 0.3897 0.059 Uiso 1 1 calc R . . C9_1 C -0.3198(8) 1.0445(8) 0.4677(4) 0.0453(15) Uani 1 1 d . . . H9_1 H -0.4058 1.1412 0.4727 0.054 Uiso 1 1 calc R . . C10_1 C -0.3325(8) 0.9001(8) 0.5103(4) 0.0446(14) Uani 1 1 d . . . H10_1 H -0.4281 0.8984 0.5440 0.054 Uiso 1 1 calc R . . C11_1 C -0.2083(7) 0.7591(7) 0.5041(3) 0.0375(13) Uani 1 1 d . . . H11_1 H -0.2167 0.6614 0.5345 0.045 Uiso 1 1 calc R . . C12_1 C 0.2109(6) 0.1505(6) 0.2914(3) 0.0275(11) Uani 1 1 d . . . C13_1 C 0.3428(7) 0.0750(7) 0.3360(3) 0.0342(12) Uani 1 1 d . . . H13_1 H 0.3654 0.1293 0.3764 0.041 Uiso 1 1 calc R . . C14_1 C 0.4401(8) -0.0779(8) 0.3218(4) 0.0435(14) Uani 1 1 d . . . H14_1 H 0.5321 -0.1262 0.3510 0.052 Uiso 1 1 calc R . . C15_1 C 0.4045(8) -0.1609(7) 0.2654(4) 0.0446(15) Uani 1 1 d . . . H15_1 H 0.4706 -0.2668 0.2562 0.054 Uiso 1 1 calc R . . C16_1 C 0.2719(8) -0.0889(7) 0.2225(3) 0.0448(15) Uani 1 1 d . . . H16_1 H 0.2465 -0.1462 0.1840 0.054 Uiso 1 1 calc R . . C17_1 C 0.1758(8) 0.0656(7) 0.2351(3) 0.0383(13) Uani 1 1 d . . . H17_1 H 0.0853 0.1139 0.2050 0.046 Uiso 1 1 calc R . . C18_1 C -0.0436(6) 0.6775(6) 0.1337(3) 0.0280(11) Uani 1 1 d . . . C19_1 C 0.0747(7) 0.7130(7) 0.0791(3) 0.0372(13) Uani 1 1 d . . . H19_1 H 0.1610 0.6274 0.0597 0.045 Uiso 1 1 calc R . . C20_1 C 0.0680(9) 0.8747(9) 0.0520(4) 0.0514(17) Uani 1 1 d . . . H20_1 H 0.1498 0.8990 0.0143 0.062 Uiso 1 1 calc R . . C21_1 C -0.0546(9) 0.9971(8) 0.0795(4) 0.0506(17) Uani 1 1 d . . . H21_1 H -0.0577 1.1068 0.0609 0.061 Uiso 1 1 calc R . . C22_1 C -0.1746(9) 0.9649(8) 0.1339(4) 0.0479(16) Uani 1 1 d . . . H22_1 H -0.2600 1.0518 0.1529 0.057 Uiso 1 1 calc R . . C23_1 C -0.1701(8) 0.8041(7) 0.1610(3) 0.0394(13) Uani 1 1 d . . . H23_1 H -0.2534 0.7807 0.1981 0.047 Uiso 1 1 calc R . . C24_1 C -0.2325(6) 0.4404(6) 0.1648(3) 0.0283(11) Uani 1 1 d . . . C25_1 C -0.3198(7) 0.3902(8) 0.2297(3) 0.0392(13) Uani 1 1 d . . . H25_1 H -0.2753 0.3728 0.2785 0.047 Uiso 1 1 calc R . . C26_1 C -0.4735(8) 0.3646(8) 0.2240(4) 0.0503(16) Uani 1 1 d . . . H26_1 H -0.5344 0.3310 0.2689 0.060 Uiso 1 1 calc R . . C27_1 C -0.5375(8) 0.3883(9) 0.1524(4) 0.0529(17) Uani 1 1 d . . . H27_1 H -0.6423 0.3708 0.1484 0.063 Uiso 1 1 calc R . . C28_1 C -0.4499(9) 0.4368(10) 0.0876(4) 0.061(2) Uani 1 1 d . . . H28_1 H -0.4931 0.4515 0.0385 0.073 Uiso 1 1 calc R . . C29_1 C -0.2988(8) 0.4642(9) 0.0936(4) 0.0493(16) Uani 1 1 d . . . H29_1 H -0.2392 0.4998 0.0486 0.059 Uiso 1 1 calc R . . P1_2 P 0.30920(15) 0.60181(14) 0.66414(7) 0.0280(3) Uani 1 1 d . . . O1_2 O 0.1133(5) 0.5936(5) 0.8855(2) 0.0399(9) Uani 1 1 d . . . N1_2 N 0.0369(6) 0.2987(6) 0.8697(3) 0.0431(12) Uani 1 1 d . . . C1_2 C 0.1219(7) 0.6572(6) 0.8087(3) 0.0309(11) Uani 1 1 d . . . O2_2 O 0.2262(5) 0.5279(4) 0.6131(2) 0.0348(9) Uani 1 1 d . . . N2_2 N -0.1059(7) 0.3765(6) 0.8849(3) 0.0437(12) Uani 1 1 d . . . C2_2 C 0.2495(6) 0.5724(6) 0.7650(3) 0.0302(11) Uani 1 1 d . . . N3_2 N -0.2409(7) 0.4416(9) 0.8922(4) 0.0672(18) Uani 1 1 d . . . C3_2 C 0.3352(7) 0.4209(7) 0.8141(3) 0.0374(13) Uani 1 1 d . . . H3A_2 H 0.4527 0.4161 0.8164 0.045 Uiso 1 1 calc R . . H3B_2 H 0.3265 0.3205 0.7938 0.045 Uiso 1 1 calc R . . C4_2 C 0.2405(7) 0.4435(6) 0.8936(3) 0.0341(12) Uani 1 1 d . . . H4_2 H 0.3166 0.4532 0.9316 0.041 Uiso 1 1 calc R . . C5_2 C 0.1563(7) 0.3068(6) 0.9249(3) 0.0322(12) Uani 1 1 d . . . H5_2 H 0.0950 0.3339 0.9759 0.039 Uiso 1 1 calc R . . C6_2 C 0.2780(7) 0.1423(6) 0.9357(3) 0.0330(12) Uani 1 1 d . . . C7_2 C 0.3028(8) 0.0249(7) 0.8833(3) 0.0430(14) Uani 1 1 d . . . H7_2 H 0.2409 0.0467 0.8393 0.052 Uiso 1 1 calc R . . C8_2 C 0.4171(9) -0.1225(8) 0.8952(4) 0.0504(16) Uani 1 1 d . . . H8_2 H 0.4318 -0.2033 0.8602 0.061 Uiso 1 1 calc R . . C9_2 C 0.5103(9) -0.1527(8) 0.9581(4) 0.0518(17) Uani 1 1 d . . . H9_2 H 0.5907 -0.2534 0.9654 0.062 Uiso 1 1 calc R . . C10_2 C 0.4875(9) -0.0385(8) 1.0098(4) 0.0523(17) Uani 1 1 d . . . H10_2 H 0.5514 -0.0607 1.0531 0.063 Uiso 1 1 calc R . . C11_2 C 0.3720(8) 0.1088(7) 0.9991(3) 0.0410(14) Uani 1 1 d . . . H11_2 H 0.3565 0.1876 1.0352 0.049 Uiso 1 1 calc R . . C12_2 C -0.0139(7) 0.8026(6) 0.7920(3) 0.0322(12) Uani 1 1 d . . . C13_2 C -0.0860(7) 0.9036(7) 0.8501(4) 0.0396(14) Uani 1 1 d . . . H13_2 H -0.0459 0.8813 0.9000 0.047 Uiso 1 1 calc R . . C14_2 C -0.2169(8) 1.0374(8) 0.8345(4) 0.0477(16) Uani 1 1 d . . . H14_2 H -0.2658 1.1076 0.8738 0.057 Uiso 1 1 calc R . . C15_2 C -0.2760(8) 1.0688(8) 0.7625(4) 0.0490(16) Uani 1 1 d . . . H15_2 H -0.3651 1.1610 0.7521 0.059 Uiso 1 1 calc R . . C16_2 C -0.2070(7) 0.9673(7) 0.7054(4) 0.0399(13) Uani 1 1 d . . . H16_2 H -0.2489 0.9891 0.6559 0.048 Uiso 1 1 calc R . . C17_2 C -0.0772(7) 0.8342(7) 0.7200(3) 0.0347(12) Uani 1 1 d . . . H17_2 H -0.0306 0.7636 0.6806 0.042 Uiso 1 1 calc R . . C18_2 C 0.2849(6) 0.8176(6) 0.6363(3) 0.0275(11) Uani 1 1 d . . . C19_2 C 0.2195(7) 0.8793(7) 0.5655(3) 0.0327(12) Uani 1 1 d . . . H19_2 H 0.1842 0.8102 0.5360 0.039 Uiso 1 1 calc R . . C20_2 C 0.2059(7) 1.0408(7) 0.5383(3) 0.0373(13) Uani 1 1 d . . . H20_2 H 0.1596 1.0828 0.4906 0.045 Uiso 1 1 calc R . . C21_2 C 0.2596(7) 1.1404(7) 0.5803(3) 0.0376(13) Uani 1 1 d . . . H21_2 H 0.2523 1.2506 0.5611 0.045 Uiso 1 1 calc R . . C22_2 C 0.3239(7) 1.0803(7) 0.6505(3) 0.0389(13) Uani 1 1 d . . . H22_2 H 0.3613 1.1491 0.6792 0.047 Uiso 1 1 calc R . . C23_2 C 0.3339(7) 0.9211(7) 0.6786(3) 0.0338(12) Uani 1 1 d . . . H23_2 H 0.3748 0.8817 0.7277 0.041 Uiso 1 1 calc R . . C24_2 C 0.5294(6) 0.5127(6) 0.6575(3) 0.0303(11) Uani 1 1 d . . . C25_2 C 0.6357(7) 0.5521(7) 0.7040(3) 0.0345(12) Uani 1 1 d . . . H25_2 H 0.5922 0.6273 0.7417 0.041 Uiso 1 1 calc R . . C26_2 C 0.8021(7) 0.4828(7) 0.6955(3) 0.0384(13) Uani 1 1 d . . . H26_2 H 0.8729 0.5105 0.7273 0.046 Uiso 1 1 calc R . . C27_2 C 0.8665(7) 0.3740(8) 0.6413(4) 0.0447(15) Uani 1 1 d . . . H27_2 H 0.9817 0.3271 0.6357 0.054 Uiso 1 1 calc R . . C28_2 C 0.7650(8) 0.3318(7) 0.5948(4) 0.0431(14) Uani 1 1 d . . . H28_2 H 0.8104 0.2548 0.5580 0.052 Uiso 1 1 calc R . . C29_2 C 0.5959(7) 0.4026(6) 0.6020(3) 0.0345(12) Uani 1 1 d . . . H29_2 H 0.5262 0.3761 0.5692 0.041 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_1 0.0248(7) 0.0290(7) 0.0255(6) -0.0010(5) -0.0030(5) -0.0063(6) O1_1 0.053(2) 0.026(2) 0.0278(18) -0.0038(14) -0.0083(17) 0.0010(18) O2_1 0.032(2) 0.036(2) 0.0310(19) -0.0047(15) 0.0010(15) -0.0039(17) N1_1 0.037(3) 0.039(3) 0.055(3) 0.004(2) 0.001(2) -0.005(2) N2_1 0.040(3) 0.053(3) 0.041(3) -0.006(2) -0.002(2) -0.005(3) N3_1 0.043(4) 0.092(5) 0.060(4) -0.003(3) -0.002(3) 0.014(3) C1_1 0.030(3) 0.028(3) 0.028(2) -0.002(2) -0.004(2) -0.009(2) C2_1 0.030(3) 0.029(3) 0.028(3) -0.002(2) -0.007(2) -0.005(2) C3_1 0.044(3) 0.038(3) 0.031(3) -0.008(2) -0.011(2) -0.002(3) C4_1 0.038(3) 0.030(3) 0.033(3) -0.001(2) 0.000(2) -0.004(2) C5_1 0.036(3) 0.038(3) 0.028(3) 0.000(2) -0.003(2) -0.008(2) C6_1 0.037(3) 0.028(3) 0.029(3) -0.005(2) -0.006(2) -0.007(2) C7_1 0.041(3) 0.033(3) 0.044(3) -0.003(2) 0.000(3) -0.010(3) C8_1 0.055(4) 0.031(3) 0.058(4) 0.001(3) -0.011(3) -0.005(3) C9_1 0.042(3) 0.038(4) 0.050(4) -0.011(3) -0.011(3) 0.005(3) C10_1 0.041(3) 0.045(4) 0.042(3) -0.006(3) 0.002(3) -0.004(3) C11_1 0.044(3) 0.032(3) 0.034(3) 0.002(2) 0.002(2) -0.009(3) C12_1 0.033(3) 0.022(3) 0.027(2) 0.0017(19) 0.001(2) -0.009(2) C13_1 0.037(3) 0.036(3) 0.030(3) -0.003(2) -0.002(2) -0.009(2) C14_1 0.035(3) 0.043(4) 0.048(3) 0.002(3) -0.006(3) -0.004(3) C15_1 0.044(3) 0.029(3) 0.050(3) -0.006(3) 0.009(3) 0.005(3) C16_1 0.063(4) 0.028(3) 0.043(3) -0.009(2) -0.002(3) -0.010(3) C17_1 0.047(3) 0.029(3) 0.039(3) 0.001(2) -0.010(3) -0.009(3) C18_1 0.028(3) 0.029(3) 0.028(2) 0.001(2) -0.004(2) -0.009(2) C19_1 0.040(3) 0.037(3) 0.035(3) 0.002(2) -0.005(2) -0.013(3) C20_1 0.062(4) 0.054(4) 0.046(3) 0.011(3) -0.003(3) -0.035(4) C21_1 0.071(5) 0.032(4) 0.053(4) 0.005(3) -0.014(3) -0.020(3) C22_1 0.063(4) 0.030(3) 0.049(3) -0.005(3) -0.017(3) -0.004(3) C23_1 0.046(3) 0.030(3) 0.040(3) -0.003(2) -0.007(3) -0.006(3) C24_1 0.021(2) 0.027(3) 0.037(3) -0.004(2) -0.004(2) -0.003(2) C25_1 0.035(3) 0.044(3) 0.039(3) -0.004(2) -0.004(2) -0.010(3) C26_1 0.042(4) 0.053(4) 0.060(4) -0.003(3) 0.004(3) -0.023(3) C27_1 0.031(3) 0.056(4) 0.078(5) -0.008(3) -0.008(3) -0.020(3) C28_1 0.043(4) 0.091(6) 0.055(4) 0.007(4) -0.020(3) -0.029(4) C29_1 0.043(4) 0.069(5) 0.041(3) 0.010(3) -0.012(3) -0.026(3) P1_2 0.0307(7) 0.0216(7) 0.0290(6) 0.0000(5) -0.0025(6) -0.0033(6) O1_2 0.045(2) 0.034(2) 0.0299(19) 0.0016(15) 0.0050(17) 0.0041(18) N1_2 0.037(3) 0.044(3) 0.044(3) -0.006(2) -0.004(2) -0.003(2) C1_2 0.035(3) 0.025(3) 0.031(3) 0.000(2) -0.001(2) -0.006(2) O2_2 0.035(2) 0.027(2) 0.040(2) -0.0030(15) -0.0044(17) -0.0040(17) N2_2 0.047(3) 0.048(3) 0.035(3) -0.001(2) -0.007(2) -0.010(3) C2_2 0.034(3) 0.028(3) 0.026(2) 0.003(2) -0.002(2) -0.005(2) N3_2 0.036(3) 0.091(5) 0.065(4) -0.026(3) -0.005(3) 0.008(3) C3_2 0.034(3) 0.034(3) 0.034(3) 0.004(2) 0.004(2) 0.003(2) C4_2 0.038(3) 0.025(3) 0.031(3) 0.003(2) -0.002(2) 0.002(2) C5_2 0.034(3) 0.033(3) 0.024(2) 0.001(2) -0.003(2) -0.001(2) C6_2 0.041(3) 0.028(3) 0.028(3) 0.005(2) -0.001(2) -0.010(2) C7_2 0.061(4) 0.037(3) 0.030(3) 0.003(2) -0.003(3) -0.012(3) C8_2 0.067(4) 0.035(4) 0.041(3) -0.001(3) 0.000(3) -0.002(3) C9_2 0.057(4) 0.032(3) 0.054(4) 0.008(3) 0.002(3) 0.002(3) C10_2 0.057(4) 0.046(4) 0.051(4) 0.007(3) -0.022(3) -0.007(3) C11_2 0.050(4) 0.033(3) 0.040(3) -0.002(2) -0.008(3) -0.009(3) C12_2 0.032(3) 0.024(3) 0.038(3) -0.002(2) 0.001(2) -0.005(2) C13_2 0.039(3) 0.033(3) 0.044(3) -0.006(2) -0.001(3) -0.004(3) C14_2 0.048(4) 0.033(3) 0.054(4) -0.011(3) 0.010(3) 0.003(3) C15_2 0.041(3) 0.034(4) 0.061(4) 0.008(3) -0.003(3) 0.002(3) C16_2 0.031(3) 0.034(3) 0.050(3) 0.002(3) -0.008(3) -0.002(2) C17_2 0.036(3) 0.029(3) 0.038(3) -0.001(2) -0.002(2) -0.006(2) C18_2 0.032(3) 0.020(3) 0.029(2) 0.0034(19) -0.002(2) -0.007(2) C19_2 0.038(3) 0.030(3) 0.030(3) -0.002(2) -0.008(2) -0.005(2) C20_2 0.037(3) 0.032(3) 0.036(3) 0.006(2) -0.003(2) -0.001(3) C21_2 0.035(3) 0.021(3) 0.050(3) 0.003(2) 0.006(3) -0.002(2) C22_2 0.046(3) 0.030(3) 0.043(3) -0.006(2) -0.001(3) -0.012(3) C23_2 0.039(3) 0.030(3) 0.032(3) -0.001(2) -0.007(2) -0.007(2) C24_2 0.031(3) 0.024(3) 0.034(3) 0.000(2) -0.001(2) -0.005(2) C25_2 0.037(3) 0.031(3) 0.035(3) -0.002(2) -0.004(2) -0.008(2) C26_2 0.033(3) 0.035(3) 0.046(3) 0.001(2) -0.007(3) -0.007(3) C27_2 0.029(3) 0.040(4) 0.057(4) 0.002(3) 0.004(3) -0.001(3) C28_2 0.043(3) 0.032(3) 0.045(3) -0.007(2) 0.010(3) 0.002(3) C29_2 0.042(3) 0.025(3) 0.033(3) -0.001(2) -0.005(2) -0.003(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_1 O2_1 1.490(4) . ? P1_1 C2_1 1.789(5) . ? P1_1 C24_1 1.814(5) . ? P1_1 C18_1 1.819(5) . ? O1_1 C1_1 1.383(6) . ? O1_1 C4_1 1.450(6) . ? N1_1 N2_1 1.233(7) . ? N1_1 C5_1 1.479(8) . ? N2_1 N3_1 1.113(7) . ? C1_1 C2_1 1.348(7) . ? C1_1 C12_1 1.472(7) . ? C2_1 C3_1 1.521(7) . ? C3_1 C4_1 1.528(7) . ? C3_1 H3A_1 0.9900 . ? C3_1 H3B_1 0.9900 . ? C4_1 C5_1 1.533(8) . ? C4_1 H4_1 1.0000 . ? C5_1 C6_1 1.522(8) . ? C5_1 H5_1 1.0000 . ? C6_1 C7_1 1.388(8) . ? C6_1 C11_1 1.402(8) . ? C7_1 C8_1 1.406(8) . ? C7_1 H7_1 0.9500 . ? C8_1 C9_1 1.367(10) . ? C8_1 H8_1 0.9500 . ? C9_1 C10_1 1.387(9) . ? C9_1 H9_1 0.9500 . ? C10_1 C11_1 1.379(8) . ? C10_1 H10_1 0.9500 . ? C11_1 H11_1 0.9500 . ? C12_1 C17_1 1.390(7) . ? C12_1 C13_1 1.400(7) . ? C13_1 C14_1 1.380(8) . ? C13_1 H13_1 0.9500 . ? C14_1 C15_1 1.382(9) . ? C14_1 H14_1 0.9500 . ? C15_1 C16_1 1.382(9) . ? C15_1 H15_1 0.9500 . ? C16_1 C17_1 1.381(8) . ? C16_1 H16_1 0.9500 . ? C17_1 H17_1 0.9500 . ? C18_1 C19_1 1.375(8) . ? C18_1 C23_1 1.391(8) . ? C19_1 C20_1 1.396(9) . ? C19_1 H19_1 0.9500 . ? C20_1 C21_1 1.353(10) . ? C20_1 H20_1 0.9500 . ? C21_1 C22_1 1.374(10) . ? C21_1 H21_1 0.9500 . ? C22_1 C23_1 1.393(8) . ? C22_1 H22_1 0.9500 . ? C23_1 H23_1 0.9500 . ? C24_1 C25_1 1.374(8) . ? C24_1 C29_1 1.391(8) . ? C25_1 C26_1 1.392(9) . ? C25_1 H25_1 0.9500 . ? C26_1 C27_1 1.389(10) . ? C26_1 H26_1 0.9500 . ? C27_1 C28_1 1.369(10) . ? C27_1 H27_1 0.9500 . ? C28_1 C29_1 1.378(9) . ? C28_1 H28_1 0.9500 . ? C29_1 H29_1 0.9500 . ? P1_2 O2_2 1.482(4) . ? P1_2 C2_2 1.786(5) . ? P1_2 C24_2 1.813(5) . ? P1_2 C18_2 1.814(5) . ? O1_2 C1_2 1.387(6) . ? O1_2 C4_2 1.442(6) . ? N1_2 N2_2 1.232(7) . ? N1_2 C5_2 1.492(7) . ? C1_2 C2_2 1.344(8) . ? C1_2 C12_2 1.476(7) . ? N2_2 N3_2 1.131(7) . ? C2_2 C3_2 1.521(7) . ? C3_2 C4_2 1.530(7) . ? C3_2 H3A_2 0.9900 . ? C3_2 H3B_2 0.9900 . ? C4_2 C5_2 1.544(8) . ? C4_2 H4_2 1.0000 . ? C5_2 C6_2 1.510(7) . ? C5_2 H5_2 1.0000 . ? C6_2 C11_2 1.394(8) . ? C6_2 C7_2 1.396(8) . ? C7_2 C8_2 1.378(9) . ? C7_2 H7_2 0.9500 . ? C8_2 C9_2 1.383(9) . ? C8_2 H8_2 0.9500 . ? C9_2 C10_2 1.368(10) . ? C9_2 H9_2 0.9500 . ? C10_2 C11_2 1.380(9) . ? C10_2 H10_2 0.9500 . ? C11_2 H11_2 0.9500 . ? C12_2 C13_2 1.391(8) . ? C12_2 C17_2 1.391(8) . ? C13_2 C14_2 1.389(8) . ? C13_2 H13_2 0.9500 . ? C14_2 C15_2 1.376(9) . ? C14_2 H14_2 0.9500 . ? C15_2 C16_2 1.375(9) . ? C15_2 H15_2 0.9500 . ? C16_2 C17_2 1.376(8) . ? C16_2 H16_2 0.9500 . ? C17_2 H17_2 0.9500 . ? C18_2 C23_2 1.384(7) . ? C18_2 C19_2 1.398(7) . ? C19_2 C20_2 1.385(8) . ? C19_2 H19_2 0.9500 . ? C20_2 C21_2 1.378(8) . ? C20_2 H20_2 0.9500 . ? C21_2 C22_2 1.382(8) . ? C21_2 H21_2 0.9500 . ? C22_2 C23_2 1.376(8) . ? C22_2 H22_2 0.9500 . ? C23_2 H23_2 0.9500 . ? C24_2 C29_2 1.398(7) . ? C24_2 C25_2 1.402(7) . ? C25_2 C26_2 1.375(8) . ? C25_2 H25_2 0.9500 . ? C26_2 C27_2 1.371(9) . ? C26_2 H26_2 0.9500 . ? C27_2 C28_2 1.385(9) . ? C27_2 H27_2 0.9500 . ? C28_2 C29_2 1.397(8) . ? C28_2 H28_2 0.9500 . ? C29_2 H29_2 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 O2_1 P1_1 C2_1 116.8(2) . . ? O2_1 P1_1 C24_1 112.7(2) . . ? C2_1 P1_1 C24_1 105.1(2) . . ? O2_1 P1_1 C18_1 110.5(2) . . ? C2_1 P1_1 C18_1 106.4(2) . . ? C24_1 P1_1 C18_1 104.4(2) . . ? C1_1 O1_1 C4_1 108.5(4) . . ? N2_1 N1_1 C5_1 117.1(5) . . ? N3_1 N2_1 N1_1 171.9(7) . . ? C2_1 C1_1 O1_1 112.7(4) . . ? C2_1 C1_1 C12_1 134.6(5) . . ? O1_1 C1_1 C12_1 112.7(4) . . ? C1_1 C2_1 C3_1 108.7(4) . . ? C1_1 C2_1 P1_1 130.9(4) . . ? C3_1 C2_1 P1_1 120.2(4) . . ? C2_1 C3_1 C4_1 102.3(4) . . ? C2_1 C3_1 H3A_1 111.3 . . ? C4_1 C3_1 H3A_1 111.3 . . ? C2_1 C3_1 H3B_1 111.3 . . ? C4_1 C3_1 H3B_1 111.3 . . ? H3A_1 C3_1 H3B_1 109.2 . . ? O1_1 C4_1 C3_1 105.8(4) . . ? O1_1 C4_1 C5_1 109.4(4) . . ? C3_1 C4_1 C5_1 114.1(5) . . ? O1_1 C4_1 H4_1 109.1 . . ? C3_1 C4_1 H4_1 109.1 . . ? C5_1 C4_1 H4_1 109.1 . . ? N1_1 C5_1 C6_1 108.4(5) . . ? N1_1 C5_1 C4_1 109.7(5) . . ? C6_1 C5_1 C4_1 108.2(4) . . ? N1_1 C5_1 H5_1 110.1 . . ? C6_1 C5_1 H5_1 110.1 . . ? C4_1 C5_1 H5_1 110.1 . . ? C7_1 C6_1 C11_1 120.2(5) . . ? C7_1 C6_1 C5_1 121.7(5) . . ? C11_1 C6_1 C5_1 118.1(5) . . ? C6_1 C7_1 C8_1 118.9(5) . . ? C6_1 C7_1 H7_1 120.5 . . ? C8_1 C7_1 H7_1 120.5 . . ? C9_1 C8_1 C7_1 120.9(6) . . ? C9_1 C8_1 H8_1 119.5 . . ? C7_1 C8_1 H8_1 119.5 . . ? C8_1 C9_1 C10_1 119.7(6) . . ? C8_1 C9_1 H9_1 120.2 . . ? C10_1 C9_1 H9_1 120.2 . . ? C11_1 C10_1 C9_1 120.9(6) . . ? C11_1 C10_1 H10_1 119.6 . . ? C9_1 C10_1 H10_1 119.6 . . ? C10_1 C11_1 C6_1 119.5(5) . . ? C10_1 C11_1 H11_1 120.3 . . ? C6_1 C11_1 H11_1 120.3 . . ? C17_1 C12_1 C13_1 118.7(5) . . ? C17_1 C12_1 C1_1 121.7(5) . . ? C13_1 C12_1 C1_1 119.5(5) . . ? C14_1 C13_1 C12_1 120.5(5) . . ? C14_1 C13_1 H13_1 119.8 . . ? C12_1 C13_1 H13_1 119.8 . . ? C13_1 C14_1 C15_1 120.3(5) . . ? C13_1 C14_1 H14_1 119.9 . . ? C15_1 C14_1 H14_1 119.9 . . ? C14_1 C15_1 C16_1 119.5(6) . . ? C14_1 C15_1 H15_1 120.2 . . ? C16_1 C15_1 H15_1 120.2 . . ? C17_1 C16_1 C15_1 120.7(5) . . ? C17_1 C16_1 H16_1 119.7 . . ? C15_1 C16_1 H16_1 119.7 . . ? C16_1 C17_1 C12_1 120.3(5) . . ? C16_1 C17_1 H17_1 119.8 . . ? C12_1 C17_1 H17_1 119.8 . . ? C19_1 C18_1 C23_1 119.3(5) . . ? C19_1 C18_1 P1_1 117.3(4) . . ? C23_1 C18_1 P1_1 123.4(4) . . ? C18_1 C19_1 C20_1 120.0(6) . . ? C18_1 C19_1 H19_1 120.0 . . ? C20_1 C19_1 H19_1 120.0 . . ? C21_1 C20_1 C19_1 120.2(6) . . ? C21_1 C20_1 H20_1 119.9 . . ? C19_1 C20_1 H20_1 119.9 . . ? C20_1 C21_1 C22_1 121.0(6) . . ? C20_1 C21_1 H21_1 119.5 . . ? C22_1 C21_1 H21_1 119.5 . . ? C21_1 C22_1 C23_1 119.5(6) . . ? C21_1 C22_1 H22_1 120.3 . . ? C23_1 C22_1 H22_1 120.3 . . ? C18_1 C23_1 C22_1 120.1(6) . . ? C18_1 C23_1 H23_1 120.0 . . ? C22_1 C23_1 H23_1 120.0 . . ? C25_1 C24_1 C29_1 119.4(5) . . ? C25_1 C24_1 P1_1 123.0(4) . . ? C29_1 C24_1 P1_1 117.5(4) . . ? C24_1 C25_1 C26_1 120.0(6) . . ? C24_1 C25_1 H25_1 120.0 . . ? C26_1 C25_1 H25_1 120.0 . . ? C27_1 C26_1 C25_1 119.9(6) . . ? C27_1 C26_1 H26_1 120.1 . . ? C25_1 C26_1 H26_1 120.1 . . ? C28_1 C27_1 C26_1 120.1(6) . . ? C28_1 C27_1 H27_1 119.9 . . ? C26_1 C27_1 H27_1 119.9 . . ? C27_1 C28_1 C29_1 119.9(6) . . ? C27_1 C28_1 H28_1 120.1 . . ? C29_1 C28_1 H28_1 120.1 . . ? C28_1 C29_1 C24_1 120.7(6) . . ? C28_1 C29_1 H29_1 119.6 . . ? C24_1 C29_1 H29_1 119.6 . . ? O2_2 P1_2 C2_2 114.9(2) . . ? O2_2 P1_2 C24_2 111.5(2) . . ? C2_2 P1_2 C24_2 103.6(2) . . ? O2_2 P1_2 C18_2 111.8(2) . . ? C2_2 P1_2 C18_2 109.3(2) . . ? C24_2 P1_2 C18_2 105.0(2) . . ? C1_2 O1_2 C4_2 108.2(4) . . ? N2_2 N1_2 C5_2 115.3(5) . . ? C2_2 C1_2 O1_2 113.7(4) . . ? C2_2 C1_2 C12_2 133.5(5) . . ? O1_2 C1_2 C12_2 112.8(4) . . ? N3_2 N2_2 N1_2 172.6(6) . . ? C1_2 C2_2 C3_2 108.2(4) . . ? C1_2 C2_2 P1_2 130.5(4) . . ? C3_2 C2_2 P1_2 120.9(4) . . ? C2_2 C3_2 C4_2 102.8(4) . . ? C2_2 C3_2 H3A_2 111.2 . . ? C4_2 C3_2 H3A_2 111.2 . . ? C2_2 C3_2 H3B_2 111.2 . . ? C4_2 C3_2 H3B_2 111.2 . . ? H3A_2 C3_2 H3B_2 109.1 . . ? O1_2 C4_2 C3_2 106.9(4) . . ? O1_2 C4_2 C5_2 107.5(4) . . ? C3_2 C4_2 C5_2 114.6(5) . . ? O1_2 C4_2 H4_2 109.3 . . ? C3_2 C4_2 H4_2 109.3 . . ? C5_2 C4_2 H4_2 109.3 . . ? N1_2 C5_2 C6_2 109.2(4) . . ? N1_2 C5_2 C4_2 108.9(4) . . ? C6_2 C5_2 C4_2 112.4(4) . . ? N1_2 C5_2 H5_2 108.8 . . ? C6_2 C5_2 H5_2 108.8 . . ? C4_2 C5_2 H5_2 108.8 . . ? C11_2 C6_2 C7_2 119.0(5) . . ? C11_2 C6_2 C5_2 118.6(5) . . ? C7_2 C6_2 C5_2 122.4(5) . . ? C8_2 C7_2 C6_2 120.2(6) . . ? C8_2 C7_2 H7_2 119.9 . . ? C6_2 C7_2 H7_2 119.9 . . ? C7_2 C8_2 C9_2 120.0(6) . . ? C7_2 C8_2 H8_2 120.0 . . ? C9_2 C8_2 H8_2 120.0 . . ? C10_2 C9_2 C8_2 120.5(6) . . ? C10_2 C9_2 H9_2 119.8 . . ? C8_2 C9_2 H9_2 119.8 . . ? C9_2 C10_2 C11_2 120.2(6) . . ? C9_2 C10_2 H10_2 119.9 . . ? C11_2 C10_2 H10_2 119.9 . . ? C10_2 C11_2 C6_2 120.2(6) . . ? C10_2 C11_2 H11_2 119.9 . . ? C6_2 C11_2 H11_2 119.9 . . ? C13_2 C12_2 C17_2 119.6(5) . . ? C13_2 C12_2 C1_2 119.8(5) . . ? C17_2 C12_2 C1_2 120.5(5) . . ? C14_2 C13_2 C12_2 119.5(6) . . ? C14_2 C13_2 H13_2 120.3 . . ? C12_2 C13_2 H13_2 120.3 . . ? C15_2 C14_2 C13_2 120.2(6) . . ? C15_2 C14_2 H14_2 119.9 . . ? C13_2 C14_2 H14_2 119.9 . . ? C16_2 C15_2 C14_2 120.4(6) . . ? C16_2 C15_2 H15_2 119.8 . . ? C14_2 C15_2 H15_2 119.8 . . ? C15_2 C16_2 C17_2 120.1(6) . . ? C15_2 C16_2 H16_2 120.0 . . ? C17_2 C16_2 H16_2 120.0 . . ? C16_2 C17_2 C12_2 120.3(5) . . ? C16_2 C17_2 H17_2 119.9 . . ? C12_2 C17_2 H17_2 119.9 . . ? C23_2 C18_2 C19_2 118.8(5) . . ? C23_2 C18_2 P1_2 124.2(4) . . ? C19_2 C18_2 P1_2 116.8(4) . . ? C20_2 C19_2 C18_2 120.2(5) . . ? C20_2 C19_2 H19_2 119.9 . . ? C18_2 C19_2 H19_2 119.9 . . ? C21_2 C20_2 C19_2 120.0(5) . . ? C21_2 C20_2 H20_2 120.0 . . ? C19_2 C20_2 H20_2 120.0 . . ? C20_2 C21_2 C22_2 120.1(5) . . ? C20_2 C21_2 H21_2 120.0 . . ? C22_2 C21_2 H21_2 120.0 . . ? C23_2 C22_2 C21_2 120.1(5) . . ? C23_2 C22_2 H22_2 119.9 . . ? C21_2 C22_2 H22_2 119.9 . . ? C22_2 C23_2 C18_2 120.7(5) . . ? C22_2 C23_2 H23_2 119.6 . . ? C18_2 C23_2 H23_2 119.6 . . ? C29_2 C24_2 C25_2 118.8(5) . . ? C29_2 C24_2 P1_2 118.0(4) . . ? C25_2 C24_2 P1_2 123.2(4) . . ? C26_2 C25_2 C24_2 120.7(5) . . ? C26_2 C25_2 H25_2 119.7 . . ? C24_2 C25_2 H25_2 119.7 . . ? C27_2 C26_2 C25_2 120.3(5) . . ? C27_2 C26_2 H26_2 119.9 . . ? C25_2 C26_2 H26_2 119.9 . . ? C26_2 C27_2 C28_2 120.6(5) . . ? C26_2 C27_2 H27_2 119.7 . . ? C28_2 C27_2 H27_2 119.7 . . ? C27_2 C28_2 C29_2 119.9(5) . . ? C27_2 C28_2 H28_2 120.1 . . ? C29_2 C28_2 H28_2 120.1 . . ? C28_2 C29_2 C24_2 119.8(5) . . ? C28_2 C29_2 H29_2 120.1 . . ? C24_2 C29_2 H29_2 120.1 . . ? 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 C5_1 N1_1 N2_1 N3_1 173(5) . . . . ? C4_1 O1_1 C1_1 C2_1 8.0(6) . . . . ? C4_1 O1_1 C1_1 C12_1 -171.3(4) . . . . ? O1_1 C1_1 C2_1 C3_1 1.0(6) . . . . ? C12_1 C1_1 C2_1 C3_1 -179.8(6) . . . . ? O1_1 C1_1 C2_1 P1_1 177.0(4) . . . . ? C12_1 C1_1 C2_1 P1_1 -3.8(10) . . . . ? O2_1 P1_1 C2_1 C1_1 -19.1(6) . . . . ? C24_1 P1_1 C2_1 C1_1 106.7(5) . . . . ? C18_1 P1_1 C2_1 C1_1 -142.9(5) . . . . ? O2_1 P1_1 C2_1 C3_1 156.6(4) . . . . ? C24_1 P1_1 C2_1 C3_1 -77.7(5) . . . . ? C18_1 P1_1 C2_1 C3_1 32.7(5) . . . . ? C1_1 C2_1 C3_1 C4_1 -8.9(6) . . . . ? P1_1 C2_1 C3_1 C4_1 174.6(4) . . . . ? C1_1 O1_1 C4_1 C3_1 -13.3(6) . . . . ? C1_1 O1_1 C4_1 C5_1 -136.7(4) . . . . ? C2_1 C3_1 C4_1 O1_1 13.1(6) . . . . ? C2_1 C3_1 C4_1 C5_1 133.5(5) . . . . ? N2_1 N1_1 C5_1 C6_1 150.4(5) . . . . ? N2_1 N1_1 C5_1 C4_1 -91.5(6) . . . . ? O1_1 C4_1 C5_1 N1_1 59.3(5) . . . . ? C3_1 C4_1 C5_1 N1_1 -59.0(6) . . . . ? O1_1 C4_1 C5_1 C6_1 177.5(4) . . . . ? C3_1 C4_1 C5_1 C6_1 59.1(6) . . . . ? N1_1 C5_1 C6_1 C7_1 13.8(7) . . . . ? C4_1 C5_1 C6_1 C7_1 -105.1(6) . . . . ? N1_1 C5_1 C6_1 C11_1 -169.2(5) . . . . ? C4_1 C5_1 C6_1 C11_1 71.9(6) . . . . ? C11_1 C6_1 C7_1 C8_1 -1.0(8) . . . . ? C5_1 C6_1 C7_1 C8_1 175.9(5) . . . . ? C6_1 C7_1 C8_1 C9_1 -0.1(9) . . . . ? C7_1 C8_1 C9_1 C10_1 0.3(9) . . . . ? C8_1 C9_1 C10_1 C11_1 0.6(9) . . . . ? C9_1 C10_1 C11_1 C6_1 -1.7(9) . . . . ? C7_1 C6_1 C11_1 C10_1 1.9(8) . . . . ? C5_1 C6_1 C11_1 C10_1 -175.2(5) . . . . ? C2_1 C1_1 C12_1 C17_1 -27.6(9) . . . . ? O1_1 C1_1 C12_1 C17_1 151.6(5) . . . . ? C2_1 C1_1 C12_1 C13_1 155.5(6) . . . . ? O1_1 C1_1 C12_1 C13_1 -25.3(7) . . . . ? C17_1 C12_1 C13_1 C14_1 2.9(8) . . . . ? C1_1 C12_1 C13_1 C14_1 179.9(5) . . . . ? C12_1 C13_1 C14_1 C15_1 -2.7(9) . . . . ? C13_1 C14_1 C15_1 C16_1 0.9(10) . . . . ? C14_1 C15_1 C16_1 C17_1 0.6(10) . . . . ? C15_1 C16_1 C17_1 C12_1 -0.3(9) . . . . ? C13_1 C12_1 C17_1 C16_1 -1.4(8) . . . . ? C1_1 C12_1 C17_1 C16_1 -178.4(5) . . . . ? O2_1 P1_1 C18_1 C19_1 -13.0(5) . . . . ? C2_1 P1_1 C18_1 C19_1 114.7(4) . . . . ? C24_1 P1_1 C18_1 C19_1 -134.4(4) . . . . ? O2_1 P1_1 C18_1 C23_1 166.3(4) . . . . ? C2_1 P1_1 C18_1 C23_1 -66.1(5) . . . . ? C24_1 P1_1 C18_1 C23_1 44.8(5) . . . . ? C23_1 C18_1 C19_1 C20_1 0.6(8) . . . . ? P1_1 C18_1 C19_1 C20_1 179.9(5) . . . . ? C18_1 C19_1 C20_1 C21_1 0.1(9) . . . . ? C19_1 C20_1 C21_1 C22_1 -0.3(10) . . . . ? C20_1 C21_1 C22_1 C23_1 -0.1(10) . . . . ? C19_1 C18_1 C23_1 C22_1 -1.1(8) . . . . ? P1_1 C18_1 C23_1 C22_1 179.7(4) . . . . ? C21_1 C22_1 C23_1 C18_1 0.8(9) . . . . ? O2_1 P1_1 C24_1 C25_1 120.0(5) . . . . ? C2_1 P1_1 C24_1 C25_1 -8.2(5) . . . . ? C18_1 P1_1 C24_1 C25_1 -120.0(5) . . . . ? O2_1 P1_1 C24_1 C29_1 -55.4(5) . . . . ? C2_1 P1_1 C24_1 C29_1 176.3(5) . . . . ? C18_1 P1_1 C24_1 C29_1 64.5(5) . . . . ? C29_1 C24_1 C25_1 C26_1 -0.4(9) . . . . ? P1_1 C24_1 C25_1 C26_1 -175.8(5) . . . . ? C24_1 C25_1 C26_1 C27_1 0.7(10) . . . . ? C25_1 C26_1 C27_1 C28_1 -0.1(11) . . . . ? C26_1 C27_1 C28_1 C29_1 -0.9(12) . . . . ? C27_1 C28_1 C29_1 C24_1 1.2(12) . . . . ? C25_1 C24_1 C29_1 C28_1 -0.5(10) . . . . ? P1_1 C24_1 C29_1 C28_1 175.1(6) . . . . ? C4_2 O1_2 C1_2 C2_2 -4.7(6) . . . . ? C4_2 O1_2 C1_2 C12_2 174.1(5) . . . . ? C5_2 N1_2 N2_2 N3_2 -178(5) . . . . ? O1_2 C1_2 C2_2 C3_2 5.5(6) . . . . ? C12_2 C1_2 C2_2 C3_2 -173.0(6) . . . . ? O1_2 C1_2 C2_2 P1_2 178.2(4) . . . . ? C12_2 C1_2 C2_2 P1_2 -0.3(10) . . . . ? O2_2 P1_2 C2_2 C1_2 -84.7(6) . . . . ? C24_2 P1_2 C2_2 C1_2 153.4(5) . . . . ? C18_2 P1_2 C2_2 C1_2 41.9(6) . . . . ? O2_2 P1_2 C2_2 C3_2 87.2(5) . . . . ? C24_2 P1_2 C2_2 C3_2 -34.7(5) . . . . ? C18_2 P1_2 C2_2 C3_2 -146.2(4) . . . . ? C1_2 C2_2 C3_2 C4_2 -3.9(6) . . . . ? P1_2 C2_2 C3_2 C4_2 -177.4(4) . . . . ? C1_2 O1_2 C4_2 C3_2 1.8(6) . . . . ? C1_2 O1_2 C4_2 C5_2 -121.6(4) . . . . ? C2_2 C3_2 C4_2 O1_2 1.2(6) . . . . ? C2_2 C3_2 C4_2 C5_2 120.1(5) . . . . ? N2_2 N1_2 C5_2 C6_2 142.3(5) . . . . ? N2_2 N1_2 C5_2 C4_2 -94.7(6) . . . . ? O1_2 C4_2 C5_2 N1_2 58.8(5) . . . . ? C3_2 C4_2 C5_2 N1_2 -59.8(6) . . . . ? O1_2 C4_2 C5_2 C6_2 179.8(4) . . . . ? C3_2 C4_2 C5_2 C6_2 61.2(6) . . . . ? N1_2 C5_2 C6_2 C11_2 -163.1(5) . . . . ? C4_2 C5_2 C6_2 C11_2 76.0(6) . . . . ? N1_2 C5_2 C6_2 C7_2 18.8(7) . . . . ? C4_2 C5_2 C6_2 C7_2 -102.1(6) . . . . ? C11_2 C6_2 C7_2 C8_2 0.9(9) . . . . ? C5_2 C6_2 C7_2 C8_2 179.1(6) . . . . ? C6_2 C7_2 C8_2 C9_2 -1.6(10) . . . . ? C7_2 C8_2 C9_2 C10_2 1.5(11) . . . . ? C8_2 C9_2 C10_2 C11_2 -0.6(11) . . . . ? C9_2 C10_2 C11_2 C6_2 -0.1(10) . . . . ? C7_2 C6_2 C11_2 C10_2 -0.1(9) . . . . ? C5_2 C6_2 C11_2 C10_2 -178.3(6) . . . . ? C2_2 C1_2 C12_2 C13_2 -152.5(6) . . . . ? O1_2 C1_2 C12_2 C13_2 29.0(7) . . . . ? C2_2 C1_2 C12_2 C17_2 31.3(9) . . . . ? O1_2 C1_2 C12_2 C17_2 -147.1(5) . . . . ? C17_2 C12_2 C13_2 C14_2 -1.9(8) . . . . ? C1_2 C12_2 C13_2 C14_2 -178.1(6) . . . . ? C12_2 C13_2 C14_2 C15_2 0.7(9) . . . . ? C13_2 C14_2 C15_2 C16_2 0.5(10) . . . . ? C14_2 C15_2 C16_2 C17_2 -0.5(10) . . . . ? C15_2 C16_2 C17_2 C12_2 -0.8(9) . . . . ? C13_2 C12_2 C17_2 C16_2 2.0(8) . . . . ? C1_2 C12_2 C17_2 C16_2 178.1(5) . . . . ? O2_2 P1_2 C18_2 C23_2 172.6(4) . . . . ? C2_2 P1_2 C18_2 C23_2 44.3(5) . . . . ? C24_2 P1_2 C18_2 C23_2 -66.4(5) . . . . ? O2_2 P1_2 C18_2 C19_2 -10.5(5) . . . . ? C2_2 P1_2 C18_2 C19_2 -138.9(4) . . . . ? C24_2 P1_2 C18_2 C19_2 110.5(4) . . . . ? C23_2 C18_2 C19_2 C20_2 0.7(8) . . . . ? P1_2 C18_2 C19_2 C20_2 -176.4(4) . . . . ? C18_2 C19_2 C20_2 C21_2 1.1(9) . . . . ? C19_2 C20_2 C21_2 C22_2 -1.3(9) . . . . ? C20_2 C21_2 C22_2 C23_2 -0.3(9) . . . . ? C21_2 C22_2 C23_2 C18_2 2.1(9) . . . . ? C19_2 C18_2 C23_2 C22_2 -2.3(8) . . . . ? P1_2 C18_2 C23_2 C22_2 174.5(5) . . . . ? O2_2 P1_2 C24_2 C29_2 6.4(5) . . . . ? C2_2 P1_2 C24_2 C29_2 130.6(4) . . . . ? C18_2 P1_2 C24_2 C29_2 -114.8(4) . . . . ? O2_2 P1_2 C24_2 C25_2 -175.2(4) . . . . ? C2_2 P1_2 C24_2 C25_2 -51.0(5) . . . . ? C18_2 P1_2 C24_2 C25_2 63.6(5) . . . . ? C29_2 C24_2 C25_2 C26_2 -0.5(8) . . . . ? P1_2 C24_2 C25_2 C26_2 -178.8(4) . . . . ? C24_2 C25_2 C26_2 C27_2 0.0(8) . . . . ? C25_2 C26_2 C27_2 C28_2 -0.3(9) . . . . ? C26_2 C27_2 C28_2 C29_2 1.1(9) . . . . ? C27_2 C28_2 C29_2 C24_2 -1.6(8) . . . . ? C25_2 C24_2 C29_2 C28_2 1.3(7) . . . . ? P1_2 C24_2 C29_2 C28_2 179.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.601 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.098