# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr B Rawlings' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester LE1 7RH UNITED KINGDOM ; _publ_contact_author_email BJR2@LE.AC.UK _publ_section_title ; Triol protection with 6-benzoyl-3,4-dihydro-(2H)-pyran ; loop_ _publ_author_name 'B. Rawlings' 'Caroline D. L. Baker' 'John Fawcett' 'Christopher D. Insley' 'Derek S. Messenger' ; C.L.Newland ; 'Helen L. Overend' 'Anup K. B. Patel' 'Mufakhrul Shah' 'Bhavna Vara' 'Davinder Virdee' data_9994=5' _database_code_depnum_ccdc_archive 'CCDC 257569' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H28 N2 O12' _chemical_formula_sum 'C31 H28 N2 O12' _chemical_formula_weight 620.55 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' _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 10.110(2) _cell_length_b 11.449(2) _cell_length_c 14.007(3) _cell_angle_alpha 79.04(2) _cell_angle_beta 79.75(1) _cell_angle_gamma 70.44(1) _cell_volume 1488.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 5.35 _cell_measurement_theta_max 12.71 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(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 'Siemens P4 diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 6201 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5850 _reflns_number_gt 3968 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0668P)^2^+0.0374P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5850 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.002 _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 O3 O 0.15989(14) 0.71583(12) 0.22110(10) 0.0299(3) Uani 1 1 d . . . O1 O 0.33441(15) 0.49786(12) 0.30511(10) 0.0351(4) Uani 1 1 d . . . O2 O 0.45485(15) 0.60706(13) 0.18239(10) 0.0343(4) Uani 1 1 d . . . O4 O 0.29360(14) 0.82593(12) 0.25080(9) 0.0276(3) Uani 1 1 d . . . O5 O 0.04607(13) 0.98279(12) 0.18183(10) 0.0292(3) Uani 1 1 d . . . O6 O -0.08333(15) 1.10834(13) 0.06402(10) 0.0373(4) Uani 1 1 d . . . O7 O -0.66848(16) 1.04931(17) 0.38958(13) 0.0551(5) Uani 1 1 d . . . O8 O -0.53219(17) 0.88600(17) 0.46969(14) 0.0576(5) Uani 1 1 d . . . O9 O 0.12138(15) 1.19958(12) 0.13286(11) 0.0343(3) Uani 1 1 d . . . O10 O 0.23347(16) 1.29197(14) 0.20430(12) 0.0467(4) Uani 1 1 d . . . O11 O -0.38421(17) 1.75300(15) 0.01859(12) 0.0481(4) Uani 1 1 d . . . O12 O -0.3283(3) 1.83598(18) 0.1236(2) 0.1003(9) Uani 1 1 d . . . N1 N -0.55162(19) 0.97368(19) 0.40295(15) 0.0433(5) Uani 1 1 d . . . N2 N -0.3126(2) 1.74841(18) 0.08158(16) 0.0484(5) Uani 1 1 d . . . C1 C 0.4439(2) 0.37818(19) 0.30566(17) 0.0431(6) Uani 1 1 d . . . H1A H 0.4925 0.3701 0.2399 0.052 Uiso 1 1 calc R . . H1B H 0.4012 0.3117 0.3258 0.052 Uiso 1 1 calc R . . C2 C 0.5493(3) 0.3642(2) 0.37412(18) 0.0464(6) Uani 1 1 d . . . H2A H 0.6246 0.2855 0.3696 0.056 Uiso 1 1 calc R . . H2B H 0.5030 0.3627 0.4410 0.056 Uiso 1 1 calc R . . C3 C 0.6120(2) 0.4715(2) 0.34889(17) 0.0430(6) Uani 1 1 d . . . H3A H 0.6697 0.4663 0.2857 0.052 Uiso 1 1 calc R . . H3B H 0.6717 0.4658 0.3977 0.052 Uiso 1 1 calc R . . C4 C 0.4925(2) 0.59634(19) 0.34578(16) 0.0346(5) Uani 1 1 d . . . H4A H 0.4456 0.6075 0.4116 0.041 Uiso 1 1 calc R . . H4B H 0.5321 0.6643 0.3212 0.041 Uiso 1 1 calc R . . C5 C 0.3850(2) 0.60142(17) 0.28067(14) 0.0287(4) Uani 1 1 d . . . C6 C 0.2502(2) 0.71736(17) 0.28768(14) 0.0273(4) Uani 1 1 d . . . C7 C 0.3623(2) 0.63174(19) 0.10940(15) 0.0365(5) Uani 1 1 d . . . H7A H 0.3302 0.5601 0.1121 0.044 Uiso 1 1 calc R . . H7B H 0.4123 0.6464 0.0447 0.044 Uiso 1 1 calc R . . C8 C 0.2364(2) 0.74612(18) 0.12810(15) 0.0325(5) Uani 1 1 d . . . H8A H 0.1763 0.7729 0.0752 0.039 Uiso 1 1 calc R . . C9 C 0.2831(2) 0.85288(17) 0.14718(14) 0.0276(4) Uani 1 1 d . . . H9A H 0.3763 0.8488 0.1105 0.033 Uiso 1 1 calc R . . C10 C 0.1797(2) 0.98338(17) 0.12479(14) 0.0266(4) Uani 1 1 d . . . H10A H 0.1693 1.0025 0.0548 0.032 Uiso 1 1 calc R . . C11 C -0.0748(2) 1.04557(17) 0.14364(15) 0.0283(4) Uani 1 1 d . . . C12 C -0.1976(2) 1.02543(18) 0.21269(15) 0.0297(5) Uani 1 1 d . . . C13 C -0.1794(2) 0.9391(2) 0.29779(17) 0.0398(5) Uani 1 1 d . . . H13A H -0.0887 0.8938 0.3130 0.048 Uiso 1 1 calc R . . C14 C -0.2950(2) 0.9206(2) 0.35950(17) 0.0440(6) Uani 1 1 d . . . H14A H -0.2838 0.8619 0.4158 0.053 Uiso 1 1 calc R . . C15 C -0.4282(2) 0.99156(19) 0.33556(16) 0.0359(5) Uani 1 1 d . . . C16 C -0.4501(2) 1.07871(19) 0.25256(16) 0.0349(5) Uani 1 1 d . . . H16A H -0.5411 1.1255 0.2387 0.042 Uiso 1 1 calc R . . C17 C -0.3335(2) 1.09435(18) 0.19094(16) 0.0328(5) Uani 1 1 d . . . H17A H -0.3456 1.1517 0.1340 0.039 Uiso 1 1 calc R . . C18 C 0.2279(2) 1.07982(17) 0.15469(15) 0.0308(5) Uani 1 1 d . . . H18A H 0.2372 1.0618 0.2241 0.037 Uiso 1 1 calc R . . H18B H 0.3188 1.0806 0.1185 0.037 Uiso 1 1 calc R . . C19 C 0.1349(2) 1.29741(18) 0.16511(15) 0.0298(5) Uani 1 1 d . . . C20 C 0.0132(2) 1.41275(18) 0.14557(14) 0.0289(4) Uani 1 1 d . . . C21 C -0.0944(2) 1.41377(18) 0.09554(15) 0.0319(5) Uani 1 1 d . . . H21A H -0.0939 1.3406 0.0757 0.038 Uiso 1 1 calc R . . C22 C -0.2021(2) 1.52406(19) 0.07533(15) 0.0336(5) Uani 1 1 d . . . H22A H -0.2742 1.5265 0.0412 0.040 Uiso 1 1 calc R . . C23 C -0.2002(2) 1.62999(19) 0.10687(16) 0.0362(5) Uani 1 1 d . . . C24 C -0.0971(2) 1.6309(2) 0.15888(17) 0.0426(6) Uani 1 1 d . . . H24A H -0.1003 1.7037 0.1807 0.051 Uiso 1 1 calc R . . C25 C 0.0111(2) 1.52099(19) 0.17771(16) 0.0370(5) Uani 1 1 d . . . H25A H 0.0827 1.5194 0.2119 0.044 Uiso 1 1 calc R . . C26 C 0.1656(2) 0.72854(18) 0.38795(15) 0.0307(5) Uani 1 1 d . . . C27 C 0.0759(3) 0.6565(2) 0.42242(18) 0.0480(6) Uani 1 1 d . . . H27A H 0.0724 0.5983 0.3856 0.058 Uiso 1 1 calc R . . C28 C -0.0084(3) 0.6714(3) 0.5115(2) 0.0623(8) Uani 1 1 d . . . H28A H -0.0685 0.6231 0.5342 0.075 Uiso 1 1 calc R . . C29 C -0.0039(3) 0.7569(3) 0.5666(2) 0.0620(8) Uani 1 1 d . . . H29A H -0.0613 0.7671 0.6261 0.074 Uiso 1 1 calc R . . C30 C 0.0856(3) 0.8273(3) 0.53341(18) 0.0567(7) Uani 1 1 d . . . H30A H 0.0901 0.8842 0.5712 0.068 Uiso 1 1 calc R . . C31 C 0.1696(2) 0.8141(2) 0.44389(16) 0.0419(6) Uani 1 1 d . . . H31A H 0.2290 0.8631 0.4215 0.050 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 O3 0.0340(8) 0.0254(7) 0.0306(8) 0.0007(6) -0.0152(6) -0.0066(6) O1 0.0419(8) 0.0191(7) 0.0426(9) -0.0013(6) -0.0168(7) -0.0028(6) O2 0.0364(8) 0.0300(8) 0.0276(8) -0.0025(6) -0.0107(6) 0.0039(6) O4 0.0340(7) 0.0215(7) 0.0269(7) 0.0018(5) -0.0120(6) -0.0069(6) O5 0.0248(7) 0.0258(7) 0.0328(8) 0.0035(6) -0.0105(6) -0.0029(6) O6 0.0367(8) 0.0358(8) 0.0340(8) 0.0030(7) -0.0161(7) -0.0027(7) O7 0.0260(8) 0.0638(12) 0.0665(12) -0.0030(9) -0.0084(8) -0.0043(8) O8 0.0450(10) 0.0569(11) 0.0658(12) 0.0137(9) -0.0095(9) -0.0201(9) O9 0.0345(8) 0.0214(7) 0.0457(9) -0.0013(6) -0.0178(7) -0.0024(6) O10 0.0405(9) 0.0378(9) 0.0655(11) -0.0138(8) -0.0249(8) -0.0039(7) O11 0.0414(9) 0.0394(9) 0.0489(10) 0.0052(8) -0.0034(8) -0.0010(7) O12 0.1006(17) 0.0427(12) 0.156(2) -0.0514(14) -0.0593(17) 0.0227(11) N1 0.0329(11) 0.0454(12) 0.0525(12) -0.0053(10) -0.0095(9) -0.0122(9) N2 0.0466(12) 0.0290(11) 0.0601(14) -0.0071(10) -0.0060(11) 0.0005(9) C1 0.0562(15) 0.0202(10) 0.0462(14) -0.0012(9) -0.0213(11) 0.0027(10) C2 0.0541(15) 0.0288(12) 0.0460(14) 0.0027(10) -0.0224(12) 0.0045(11) C3 0.0395(13) 0.0409(13) 0.0400(13) -0.0008(10) -0.0173(10) 0.0024(10) C4 0.0357(12) 0.0313(11) 0.0349(11) -0.0022(9) -0.0153(9) -0.0040(9) C5 0.0334(11) 0.0217(10) 0.0275(10) -0.0011(8) -0.0093(9) -0.0025(8) C6 0.0316(11) 0.0210(9) 0.0307(11) -0.0002(8) -0.0144(9) -0.0067(8) C7 0.0476(13) 0.0303(11) 0.0271(11) -0.0053(9) -0.0142(10) -0.0006(10) C8 0.0407(12) 0.0278(11) 0.0269(11) 0.0002(8) -0.0161(9) -0.0039(9) C9 0.0270(10) 0.0258(10) 0.0259(10) 0.0002(8) -0.0084(8) -0.0025(8) C10 0.0259(10) 0.0245(10) 0.0261(10) 0.0021(8) -0.0073(8) -0.0043(8) C11 0.0308(11) 0.0187(9) 0.0337(11) -0.0038(8) -0.0148(9) 0.0000(8) C12 0.0292(11) 0.0230(10) 0.0363(11) -0.0048(8) -0.0108(9) -0.0034(8) C13 0.0281(11) 0.0379(13) 0.0466(13) 0.0071(10) -0.0144(10) -0.0037(10) C14 0.0331(12) 0.0430(13) 0.0465(14) 0.0107(11) -0.0108(11) -0.0057(10) C15 0.0266(11) 0.0328(12) 0.0472(13) -0.0042(10) -0.0083(10) -0.0069(9) C16 0.0267(11) 0.0272(11) 0.0504(14) -0.0078(10) -0.0151(10) -0.0013(9) C17 0.0325(11) 0.0241(10) 0.0396(12) -0.0009(9) -0.0154(10) -0.0022(9) C18 0.0270(10) 0.0220(10) 0.0384(12) 0.0038(8) -0.0124(9) -0.0012(8) C19 0.0302(11) 0.0290(11) 0.0305(11) -0.0033(8) -0.0047(9) -0.0095(9) C20 0.0316(11) 0.0255(10) 0.0277(10) -0.0030(8) -0.0020(9) -0.0076(9) C21 0.0337(11) 0.0257(11) 0.0363(12) -0.0062(9) -0.0052(9) -0.0079(9) C22 0.0307(11) 0.0302(11) 0.0378(12) -0.0036(9) -0.0067(9) -0.0063(9) C23 0.0363(12) 0.0275(11) 0.0390(12) -0.0050(9) -0.0028(10) -0.0030(9) C24 0.0491(14) 0.0275(11) 0.0529(15) -0.0153(10) -0.0085(11) -0.0079(10) C25 0.0406(13) 0.0348(12) 0.0384(12) -0.0074(10) -0.0096(10) -0.0116(10) C26 0.0288(11) 0.0236(10) 0.0328(11) 0.0020(8) -0.0097(9) 0.0006(8) C27 0.0540(15) 0.0364(13) 0.0485(15) 0.0014(11) -0.0033(12) -0.0131(11) C28 0.0578(17) 0.0529(17) 0.0565(17) 0.0129(14) 0.0099(14) -0.0115(14) C29 0.0527(17) 0.0637(18) 0.0405(15) 0.0031(13) 0.0074(13) 0.0073(14) C30 0.0606(17) 0.0575(17) 0.0401(14) -0.0172(12) -0.0046(13) 0.0018(14) C31 0.0429(13) 0.0403(13) 0.0406(13) -0.0102(10) -0.0068(11) -0.0071(11) _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 O3 C6 1.422(2) . ? O3 C8 1.437(2) . ? O1 C5 1.405(2) . ? O1 C1 1.444(2) . ? O2 C5 1.431(2) . ? O2 C7 1.434(2) . ? O4 C6 1.430(2) . ? O4 C9 1.441(2) . ? O5 C11 1.339(2) . ? O5 C10 1.444(2) . ? O6 C11 1.207(2) . ? O7 N1 1.230(2) . ? O8 N1 1.223(2) . ? O9 C19 1.340(2) . ? O9 C18 1.450(2) . ? O10 C19 1.199(2) . ? O11 N2 1.220(3) . ? O12 N2 1.209(3) . ? N1 C15 1.472(3) . ? N2 C23 1.478(3) . ? C1 C2 1.508(3) . ? C2 C3 1.520(3) . ? C3 C4 1.531(3) . ? C4 C5 1.519(3) . ? C5 C6 1.556(3) . ? C6 C26 1.512(3) . ? C7 C8 1.516(3) . ? C8 C9 1.531(3) . ? C9 C10 1.522(3) . ? C10 C18 1.497(3) . ? C11 C12 1.486(3) . ? C12 C17 1.391(3) . ? C12 C13 1.393(3) . ? C13 C14 1.377(3) . ? C14 C15 1.382(3) . ? C15 C16 1.378(3) . ? C16 C17 1.374(3) . ? C19 C20 1.493(3) . ? C20 C25 1.389(3) . ? C20 C21 1.391(3) . ? C21 C22 1.383(3) . ? C22 C23 1.374(3) . ? C23 C24 1.378(3) . ? C24 C25 1.380(3) . ? C26 C31 1.380(3) . ? C26 C27 1.389(3) . ? C27 C28 1.385(4) . ? C28 C29 1.373(4) . ? C29 C30 1.371(4) . ? C30 C31 1.387(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 C6 O3 C8 101.82(14) . . ? C5 O1 C1 114.22(16) . . ? C5 O2 C7 113.72(15) . . ? C6 O4 C9 107.25(14) . . ? C11 O5 C10 119.80(15) . . ? C19 O9 C18 116.55(15) . . ? O8 N1 O7 123.7(2) . . ? O8 N1 C15 118.44(18) . . ? O7 N1 C15 117.81(19) . . ? O12 N2 O11 123.3(2) . . ? O12 N2 C23 118.5(2) . . ? O11 N2 C23 118.16(19) . . ? O1 C1 C2 111.51(18) . . ? C1 C2 C3 110.97(18) . . ? C2 C3 C4 109.53(19) . . ? C5 C4 C3 111.39(17) . . ? O1 C5 O2 110.91(15) . . ? O1 C5 C4 112.67(16) . . ? O2 C5 C4 106.21(16) . . ? O1 C5 C6 104.76(16) . . ? O2 C5 C6 109.08(15) . . ? C4 C5 C6 113.25(16) . . ? O3 C6 O4 105.13(14) . . ? O3 C6 C26 108.43(16) . . ? O4 C6 C26 110.88(16) . . ? O3 C6 C5 108.61(15) . . ? O4 C6 C5 107.10(16) . . ? C26 C6 C5 116.12(15) . . ? O2 C7 C8 109.07(16) . . ? O3 C8 C7 107.52(16) . . ? O3 C8 C9 101.92(15) . . ? C7 C8 C9 111.34(17) . . ? O4 C9 C10 108.93(15) . . ? O4 C9 C8 103.21(15) . . ? C10 C9 C8 114.97(16) . . ? O5 C10 C18 108.78(16) . . ? O5 C10 C9 106.73(15) . . ? C18 C10 C9 110.94(15) . . ? O6 C11 O5 125.10(19) . . ? O6 C11 C12 124.53(17) . . ? O5 C11 C12 110.36(16) . . ? C17 C12 C13 119.6(2) . . ? C17 C12 C11 118.82(18) . . ? C13 C12 C11 121.56(18) . . ? C14 C13 C12 120.35(19) . . ? C13 C14 C15 118.2(2) . . ? C16 C15 C14 123.0(2) . . ? C16 C15 N1 118.95(18) . . ? C14 C15 N1 118.0(2) . . ? C17 C16 C15 117.99(19) . . ? C16 C17 C12 120.83(19) . . ? O9 C18 C10 106.74(15) . . ? O10 C19 O9 123.65(19) . . ? O10 C19 C20 124.76(19) . . ? O9 C19 C20 111.58(17) . . ? C25 C20 C21 120.41(19) . . ? C25 C20 C19 117.89(18) . . ? C21 C20 C19 121.69(18) . . ? C22 C21 C20 119.77(19) . . ? C23 C22 C21 118.4(2) . . ? C22 C23 C24 123.0(2) . . ? C22 C23 N2 118.0(2) . . ? C24 C23 N2 118.9(2) . . ? C23 C24 C25 118.3(2) . . ? C24 C25 C20 120.1(2) . . ? C31 C26 C27 119.0(2) . . ? C31 C26 C6 121.31(19) . . ? C27 C26 C6 119.6(2) . . ? C28 C27 C26 120.1(3) . . ? C29 C28 C27 120.4(3) . . ? C30 C29 C28 119.7(3) . . ? C29 C30 C31 120.4(3) . . ? C26 C31 C30 120.3(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.215 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.045 data_04182=2 _database_code_depnum_ccdc_archive 'CCDC 257570' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 O4' _chemical_formula_weight 262.29 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' _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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5600(16) _cell_length_b 12.140(2) _cell_length_c 25.374(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2636.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 724 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 24.42 _exptl_crystal_description colourless _exptl_crystal_colour block _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.095 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18818 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0785 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4634 _reflns_number_gt 3234 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 ; All crystals examined had twin components and the unit cell was derived using the program GEMINI. The orthorhombic space group P2(1) 2(1) 2(1) was used and the data refined as a racemic twin. 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^)+(0.0629P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(16) _refine_ls_number_reflns 4634 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1375 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.012 _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 O3 O 0.6468(3) 0.3202(2) 0.14640(10) 0.0352(7) Uani 1 1 d . . . O6 O 0.3949(3) 0.2237(2) 0.09048(9) 0.0334(6) Uani 1 1 d . . . O8 O 0.5266(3) 0.3593(2) 0.04820(9) 0.0360(7) Uani 1 1 d . . . O1' O 0.3994(3) 0.3406(2) 0.18328(9) 0.0326(7) Uani 1 1 d . . . C1 C 0.5550(5) 0.1850(3) 0.08517(16) 0.0435(11) Uani 1 1 d . . . H1 H 0.5588 0.1056 0.0747 0.052 Uiso 1 1 calc R . . C2 C 0.6390(5) 0.2048(3) 0.13595(17) 0.0450(11) Uani 1 1 d . . . H2A H 0.5834 0.1672 0.1650 0.054 Uiso 1 1 calc R . . H2B H 0.7459 0.1741 0.1338 0.054 Uiso 1 1 calc R . . C4 C 0.4996(4) 0.3750(3) 0.14255(14) 0.0285(9) Uani 1 1 d . . . C5 C 0.4192(4) 0.3396(3) 0.08989(13) 0.0284(9) Uani 1 1 d . . . C7 C 0.6158(5) 0.2604(3) 0.04078(15) 0.0411(11) Uani 1 1 d . . . H7A H 0.7291 0.2746 0.0447 0.049 Uiso 1 1 calc R . . H7B H 0.5959 0.2277 0.0057 0.049 Uiso 1 1 calc R . . C3' C 0.5336(5) 0.4968(3) 0.14473(16) 0.0384(10) Uani 1 1 d . . . H3'1 H 0.4375 0.5386 0.1363 0.046 Uiso 1 1 calc R . . H3'2 H 0.6138 0.5156 0.1181 0.046 Uiso 1 1 calc R . . C4' C 0.5921(5) 0.5296(4) 0.19973(18) 0.0513(13) Uani 1 1 d . . . H4'1 H 0.6982 0.4994 0.2053 0.062 Uiso 1 1 calc R . . H4'2 H 0.5983 0.6108 0.2022 0.062 Uiso 1 1 calc R . . C5' C 0.4833(6) 0.4862(4) 0.24204(18) 0.0533(12) Uani 1 1 d . . . H5'1 H 0.5291 0.5005 0.2772 0.064 Uiso 1 1 calc R . . H5'2 H 0.3820 0.5253 0.2400 0.064 Uiso 1 1 calc R . . C6' C 0.4571(5) 0.3657(4) 0.23541(15) 0.0467(12) Uani 1 1 d . . . H6'1 H 0.5566 0.3260 0.2414 0.056 Uiso 1 1 calc R . . H6'2 H 0.3808 0.3400 0.2620 0.056 Uiso 1 1 calc R . . C9 C 0.2641(4) 0.3960(3) 0.07871(14) 0.0267(9) Uani 1 1 d . . . C10 C 0.2478(5) 0.4716(3) 0.03828(14) 0.0319(10) Uani 1 1 d . . . H10 H 0.3359 0.4907 0.0174 0.038 Uiso 1 1 calc R . . C11 C 0.1044(5) 0.5198(3) 0.02792(16) 0.0391(11) Uani 1 1 d . . . H11 H 0.0945 0.5717 0.0001 0.047 Uiso 1 1 calc R . . C12 C -0.0243(5) 0.4924(3) 0.05808(16) 0.0396(10) Uani 1 1 d . . . H12 H -0.1229 0.5249 0.0507 0.048 Uiso 1 1 calc R . . C13 C -0.0095(5) 0.4170(3) 0.09934(15) 0.0370(10) Uani 1 1 d . . . H13 H -0.0975 0.3980 0.1203 0.044 Uiso 1 1 calc R . . C14 C 0.1347(4) 0.3702(3) 0.10936(14) 0.0302(9) Uani 1 1 d . . . H14 H 0.1455 0.3196 0.1377 0.036 Uiso 1 1 calc R . . O1'A O 0.9301(3) 0.8986(3) 0.19848(10) 0.0606(10) Uani 1 1 d . . . O3A O 1.1782(3) 0.9232(2) 0.16223(10) 0.0380(7) Uani 1 1 d . . . O6A O 0.9261(3) 1.0274(2) 0.11020(12) 0.0439(7) Uani 1 1 d . . . O8A O 1.0512(3) 0.8982(2) 0.06358(10) 0.0421(7) Uani 1 1 d . . . C1A C 1.0858(5) 1.0656(4) 0.10510(19) 0.0526(13) Uani 1 1 d . . . H1A H 1.0903 1.1458 0.0963 0.063 Uiso 1 1 calc R . . C2A C 1.1701(5) 1.0407(4) 0.15569(18) 0.0527(13) Uani 1 1 d . . . H2A1 H 1.2768 1.0721 0.1546 0.063 Uiso 1 1 calc R . . H2A2 H 1.1136 1.0741 0.1858 0.063 Uiso 1 1 calc R . . C4A C 1.0295(4) 0.8694(3) 0.15658(14) 0.0330(9) Uani 1 1 d . . . C5A C 0.9481(4) 0.9120(3) 0.10638(13) 0.0276(9) Uani 1 1 d . . . C7A C 1.1461(5) 0.9953(4) 0.06027(17) 0.0527(13) Uani 1 1 d . . . H7A1 H 1.1321 1.0328 0.0259 0.063 Uiso 1 1 calc R . . H7A2 H 1.2580 0.9774 0.0651 0.063 Uiso 1 1 calc R . . C3'A C 1.0641(5) 0.7487(4) 0.1546(2) 0.0613(15) Uani 1 1 d . . . H3'3 H 1.1465 0.7344 0.1281 0.074 Uiso 1 1 calc R . . H3'4 H 0.9691 0.7080 0.1438 0.074 Uiso 1 1 calc R . . C4'A C 1.1196(7) 0.7069(5) 0.2099(3) 0.108(3) Uani 1 1 d . . . H4'3 H 1.1151 0.6255 0.2112 0.130 Uiso 1 1 calc R . . H4'4 H 1.2289 0.7300 0.2163 0.130 Uiso 1 1 calc R . . C5'A C 1.0110(7) 0.7567(7) 0.2530(2) 0.102(3) Uani 1 1 d . . . H5'3 H 0.9087 0.7189 0.2513 0.123 Uiso 1 1 calc R . . H5'4 H 1.0569 0.7408 0.2880 0.123 Uiso 1 1 calc R . . C6'A C 0.9851(8) 0.8734(7) 0.2490(2) 0.099(2) Uani 1 1 d . . . H6'3 H 0.9076 0.8968 0.2757 0.119 Uiso 1 1 calc R . . H6'4 H 1.0839 0.9133 0.2557 0.119 Uiso 1 1 calc R . . C9A C 0.7925(4) 0.8575(3) 0.09589(13) 0.0275(9) Uani 1 1 d . . . C10A C 0.6599(4) 0.8889(3) 0.12354(15) 0.0341(10) Uani 1 1 d . . . H10A H 0.6671 0.9458 0.1492 0.041 Uiso 1 1 calc R . . C11A C 0.5178(5) 0.8389(3) 0.11438(15) 0.0410(11) Uani 1 1 d . . . H11A H 0.4278 0.8616 0.1334 0.049 Uiso 1 1 calc R . . C12A C 0.5069(5) 0.7555(3) 0.07727(15) 0.0426(11) Uani 1 1 d . . . H12A H 0.4094 0.7206 0.0709 0.051 Uiso 1 1 calc R . . C13A C 0.6361(5) 0.7237(3) 0.04992(16) 0.0437(11) Uani 1 1 d . . . H13A H 0.6278 0.6662 0.0246 0.052 Uiso 1 1 calc R . . C14A C 0.7791(5) 0.7736(3) 0.05836(14) 0.0340(9) Uani 1 1 d . . . H14A H 0.8680 0.7509 0.0387 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 O3 0.0317(16) 0.0294(15) 0.0446(16) 0.0026(12) -0.0021(13) 0.0039(12) O6 0.0411(16) 0.0226(15) 0.0365(16) 0.0005(12) 0.0075(13) 0.0026(12) O8 0.0408(16) 0.0345(16) 0.0327(15) 0.0070(12) 0.0175(13) 0.0041(13) O1' 0.0312(15) 0.0445(17) 0.0223(14) 0.0009(12) -0.0010(12) -0.0017(13) C1 0.048(3) 0.035(3) 0.048(3) 0.000(2) 0.003(2) 0.012(2) C2 0.045(3) 0.035(3) 0.055(3) 0.005(2) 0.007(2) 0.015(2) C4 0.0207(19) 0.031(2) 0.034(2) 0.0032(17) 0.0057(18) 0.0022(17) C5 0.032(2) 0.024(2) 0.028(2) 0.0017(16) 0.0107(18) -0.0015(17) C7 0.044(3) 0.038(3) 0.041(3) -0.003(2) 0.013(2) 0.008(2) C3' 0.034(2) 0.030(2) 0.051(3) -0.0015(19) -0.010(2) -0.0010(19) C4' 0.047(3) 0.040(3) 0.067(3) -0.011(2) -0.027(3) -0.005(2) C5' 0.048(3) 0.064(3) 0.048(3) -0.015(2) -0.009(2) 0.004(3) C6' 0.041(3) 0.070(3) 0.029(2) -0.002(2) -0.006(2) 0.007(3) C9 0.031(2) 0.023(2) 0.026(2) -0.0060(16) -0.0014(17) -0.0032(17) C10 0.034(2) 0.032(2) 0.029(2) 0.0031(18) 0.0023(18) -0.0049(19) C11 0.043(3) 0.034(2) 0.040(3) 0.009(2) -0.006(2) 0.005(2) C12 0.038(2) 0.032(2) 0.049(3) 0.001(2) -0.008(2) 0.004(2) C13 0.037(2) 0.038(2) 0.037(2) -0.0028(19) 0.006(2) -0.003(2) C14 0.032(2) 0.029(2) 0.029(2) -0.0004(17) -0.0025(18) -0.0060(18) O1'A 0.0412(18) 0.120(3) 0.0205(15) 0.0030(16) -0.0002(14) -0.0224(19) O3A 0.0333(16) 0.0452(18) 0.0355(16) 0.0049(13) 0.0016(13) -0.0053(13) O6A 0.0357(16) 0.0255(16) 0.070(2) -0.0077(14) -0.0055(15) 0.0012(13) O8A 0.0433(17) 0.0537(19) 0.0294(16) -0.0031(13) 0.0130(14) -0.0110(15) C1A 0.044(3) 0.032(3) 0.082(4) 0.014(2) -0.022(3) -0.014(2) C2A 0.046(3) 0.053(3) 0.060(3) -0.009(2) -0.007(3) -0.007(2) C4A 0.028(2) 0.041(3) 0.030(2) 0.0026(18) -0.0006(18) -0.0090(19) C5A 0.034(2) 0.024(2) 0.025(2) -0.0029(16) 0.0053(19) 0.0058(17) C7A 0.048(3) 0.070(4) 0.040(3) 0.017(2) -0.006(2) -0.016(3) C3'A 0.044(3) 0.038(3) 0.102(4) 0.027(3) -0.032(3) -0.014(2) C4'A 0.073(4) 0.085(5) 0.166(7) 0.052(5) -0.089(5) -0.014(4) C5'A 0.058(4) 0.168(8) 0.081(4) 0.063(5) -0.039(3) -0.037(5) C6'A 0.083(4) 0.170(8) 0.044(3) 0.040(4) -0.018(3) -0.047(5) C9A 0.037(2) 0.022(2) 0.024(2) 0.0038(16) -0.0025(17) 0.0029(17) C10A 0.038(2) 0.033(2) 0.031(2) 0.0001(18) 0.000(2) -0.001(2) C11A 0.038(3) 0.050(3) 0.036(2) 0.011(2) 0.000(2) 0.003(2) C12A 0.040(3) 0.043(3) 0.045(2) 0.011(2) -0.013(2) -0.011(2) C13A 0.059(3) 0.033(2) 0.039(3) -0.005(2) -0.013(2) 0.000(2) C14A 0.043(2) 0.032(2) 0.027(2) 0.0031(18) -0.0055(19) 0.005(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 O3 C2 1.427(4) . ? O3 C4 1.428(4) . ? O6 C5 1.421(4) . ? O6 C1 1.455(5) . ? O8 C5 1.422(4) . ? O8 C7 1.435(4) . ? O1' C4 1.406(4) . ? O1' C6' 1.444(4) . ? C1 C2 1.495(5) . ? C1 C7 1.542(5) . ? C4 C3' 1.508(5) . ? C4 C5 1.564(5) . ? C5 C9 1.520(5) . ? C3' C4' 1.535(5) . ? C4' C5' 1.516(6) . ? C5' C6' 1.489(6) . ? C9 C10 1.384(5) . ? C9 C14 1.389(5) . ? C10 C11 1.385(5) . ? C11 C12 1.382(6) . ? C12 C13 1.397(5) . ? C13 C14 1.382(5) . ? O1'A C6'A 1.400(6) . ? O1'A C4A 1.407(4) . ? O3A C4A 1.438(4) . ? O3A C2A 1.438(5) . ? O6A C5A 1.417(4) . ? O6A C1A 1.449(5) . ? O8A C5A 1.409(4) . ? O8A C7A 1.434(5) . ? C1A C2A 1.503(6) . ? C1A C7A 1.513(6) . ? C4A C3'A 1.496(6) . ? C4A C5A 1.541(5) . ? C5A C9A 1.511(5) . ? C3'A C4'A 1.566(7) . ? C4'A C5'A 1.557(9) . ? C5'A C6'A 1.437(9) . ? C9A C10A 1.388(5) . ? C9A C14A 1.399(5) . ? C10A C11A 1.379(5) . ? C11A C12A 1.386(6) . ? C12A C13A 1.362(6) . ? C13A C14A 1.382(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 O3 C4 113.8(3) . . ? C5 O6 C1 100.5(3) . . ? C5 O8 C7 107.5(3) . . ? C4 O1' C6' 113.7(3) . . ? O6 C1 C2 108.7(3) . . ? O6 C1 C7 101.2(3) . . ? C2 C1 C7 111.8(4) . . ? O3 C2 C1 109.9(3) . . ? O1' C4 O3 110.4(3) . . ? O1' C4 C3' 112.4(3) . . ? O3 C4 C3' 106.5(3) . . ? O1' C4 C5 106.1(3) . . ? O3 C4 C5 108.6(3) . . ? C3' C4 C5 112.7(3) . . ? O6 C5 O8 105.6(3) . . ? O6 C5 C9 108.7(3) . . ? O8 C5 C9 110.5(3) . . ? O6 C5 C4 109.1(3) . . ? O8 C5 C4 107.7(3) . . ? C9 C5 C4 114.8(3) . . ? O8 C7 C1 102.8(3) . . ? C4 C3' C4' 110.5(3) . . ? C5' C4' C3' 110.7(3) . . ? C6' C5' C4' 110.7(4) . . ? O1' C6' C5' 111.2(3) . . ? C10 C9 C14 119.0(3) . . ? C10 C9 C5 121.7(3) . . ? C14 C9 C5 119.4(3) . . ? C9 C10 C11 120.7(4) . . ? C12 C11 C10 120.0(4) . . ? C11 C12 C13 120.0(4) . . ? C14 C13 C12 119.2(4) . . ? C13 C14 C9 121.1(4) . . ? C6'A O1'A C4A 115.7(4) . . ? C4A O3A C2A 113.4(3) . . ? C5A O6A C1A 100.6(3) . . ? C5A O8A C7A 107.6(3) . . ? O6A C1A C2A 108.2(4) . . ? O6A C1A C7A 102.0(3) . . ? C2A C1A C7A 111.4(4) . . ? O3A C2A C1A 108.7(3) . . ? O1'A C4A O3A 110.2(3) . . ? O1'A C4A C3'A 113.0(4) . . ? O3A C4A C3'A 105.9(3) . . ? O1'A C4A C5A 105.5(3) . . ? O3A C4A C5A 109.3(3) . . ? C3'A C4A C5A 113.0(3) . . ? O8A C5A O6A 104.7(3) . . ? O8A C5A C9A 111.4(3) . . ? O6A C5A C9A 109.1(3) . . ? O8A C5A C4A 108.3(3) . . ? O6A C5A C4A 109.6(3) . . ? C9A C5A C4A 113.4(3) . . ? O8A C7A C1A 103.1(3) . . ? C4A C3'A C4'A 110.3(4) . . ? C5'A C4'A C3'A 108.8(4) . . ? C6'A C5'A C4'A 115.1(6) . . ? O1'A C6'A C5'A 109.4(6) . . ? C10A C9A C14A 118.5(3) . . ? C10A C9A C5A 120.8(3) . . ? C14A C9A C5A 120.7(3) . . ? C11A C10A C9A 121.0(4) . . ? C10A C11A C12A 119.7(4) . . ? C13A C12A C11A 119.9(4) . . ? C12A C13A C14A 121.0(4) . . ? C13A C14A C9A 119.8(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.361 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.049 data_2054=7' _database_code_depnum_ccdc_archive 'CCDC 257571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H30 N2 O14' _chemical_formula_weight 678.59 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' _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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.6293(16) _cell_length_b 12.9407(17) _cell_length_c 19.247(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3145.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2404 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.42 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.113 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23021 _diffrn_reflns_av_R_equivalents 0.0815 _diffrn_reflns_av_sigmaI/netI 0.0809 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5554 _reflns_number_gt 4259 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0418P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(12) _refine_ls_number_reflns 5554 _refine_ls_number_parameters 444 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 O1 O 0.61768(18) 0.27097(19) 0.70672(12) 0.0277(6) Uani 1 1 d . . . O2 O 0.73259(18) 0.13008(18) 0.71754(11) 0.0240(6) Uani 1 1 d . . . O3 O 0.77723(18) 0.30110(19) 0.80010(12) 0.0274(6) Uani 1 1 d . . . O4 O 0.90004(18) 0.25967(19) 0.71987(12) 0.0289(6) Uani 1 1 d . . . O5 O 0.69142(19) -0.05258(18) 0.76586(12) 0.0249(6) Uani 1 1 d . . . O6 O 0.8257(2) -0.0907(2) 0.69268(13) 0.0342(7) Uani 1 1 d . . . O7 O 0.4446(2) -0.2489(2) 0.45971(14) 0.0407(7) Uani 1 1 d . . . O8 O 0.3294(2) -0.2526(2) 0.54195(15) 0.0508(9) Uani 1 1 d . . . O9 O 0.64013(18) 0.00431(19) 0.90336(12) 0.0282(6) Uani 1 1 d . . . O10 O 0.6982(2) -0.0012(2) 1.01336(12) 0.0342(7) Uani 1 1 d . . . O11 O 0.1272(2) 0.0060(2) 1.01696(15) 0.0474(8) Uani 1 1 d . . . O12 O 0.1824(2) -0.0284(2) 1.12097(14) 0.0435(8) Uani 1 1 d . . . O13 O 0.6987(2) -0.1933(2) 0.91183(14) 0.0373(7) Uani 1 1 d . . . O14 O 0.8636(2) -0.15735(19) 0.87630(14) 0.0357(7) Uani 1 1 d . . . N1 N 0.4192(3) -0.2377(3) 0.52051(18) 0.0370(9) Uani 1 1 d . . . N2 N 0.1976(3) -0.0073(2) 1.05942(17) 0.0339(8) Uani 1 1 d . . . C1 C 0.5315(3) 0.2123(3) 0.6759(2) 0.0327(10) Uani 1 1 d . . . H1A H 0.4632 0.2449 0.6883 0.039 Uiso 1 1 calc R . . H1B H 0.5317 0.1413 0.6950 0.039 Uiso 1 1 calc R . . C2 C 0.5418(3) 0.2075(3) 0.59812(19) 0.0342(10) Uani 1 1 d . . . H2A H 0.5360 0.2779 0.5784 0.041 Uiso 1 1 calc R . . H2B H 0.4839 0.1649 0.5786 0.041 Uiso 1 1 calc R . . C3 C 0.6474(3) 0.1611(3) 0.57893(19) 0.0319(10) Uani 1 1 d . . . H3A H 0.6562 0.1620 0.5278 0.038 Uiso 1 1 calc R . . H3B H 0.6504 0.0883 0.5947 0.038 Uiso 1 1 calc R . . C4 C 0.7367(3) 0.2228(3) 0.61303(18) 0.0271(9) Uani 1 1 d . . . H4A H 0.8051 0.1878 0.6044 0.032 Uiso 1 1 calc R . . H4B H 0.7401 0.2925 0.5920 0.032 Uiso 1 1 calc R . . C5 C 0.7187(3) 0.2326(3) 0.69050(18) 0.0238(9) Uani 1 1 d . . . C6 C 0.7981(3) 0.3040(3) 0.72753(18) 0.0251(9) Uani 1 1 d . . . C7 C 0.9191(3) 0.1959(3) 0.7792(2) 0.0321(10) Uani 1 1 d . . . H7A H 0.9778 0.2237 0.8077 0.039 Uiso 1 1 calc R . . H7B H 0.9365 0.1243 0.7651 0.039 Uiso 1 1 calc R . . C8 C 0.8156(3) 0.1998(3) 0.81837(19) 0.0270(9) Uani 1 1 d . . . H8A H 0.8265 0.1927 0.8696 0.032 Uiso 1 1 calc R . . C9 C 0.7336(3) 0.1234(3) 0.79134(17) 0.0235(8) Uani 1 1 d . . . H9 H 0.6621 0.1407 0.8104 0.028 Uiso 1 1 calc R . . C10 C 0.7611(3) 0.0107(3) 0.80755(18) 0.0255(8) Uani 1 1 d . . . H10 H 0.8362 -0.0030 0.7938 0.031 Uiso 1 1 calc R . . C11 C 0.7331(3) -0.0903(3) 0.70560(19) 0.0248(9) Uani 1 1 d . . . C12 C 0.6498(3) -0.1315(3) 0.65983(18) 0.0240(9) Uani 1 1 d . . . C13 C 0.6796(3) -0.1665(3) 0.59521(19) 0.0276(9) Uani 1 1 d . . . H13 H 0.7523 -0.1663 0.5825 0.033 Uiso 1 1 calc R . . C14 C 0.6051(3) -0.2018(3) 0.5489(2) 0.0319(10) Uani 1 1 d . . . H14 H 0.6252 -0.2247 0.5039 0.038 Uiso 1 1 calc R . . C15 C 0.5007(3) -0.2032(3) 0.56943(19) 0.0261(9) Uani 1 1 d . . . C16 C 0.4676(3) -0.1714(3) 0.63451(19) 0.0293(9) Uani 1 1 d . . . H16 H 0.3952 -0.1747 0.6477 0.035 Uiso 1 1 calc R . . C17 C 0.5443(3) -0.1346(3) 0.6798(2) 0.0285(9) Uani 1 1 d . . . H17 H 0.5244 -0.1113 0.7248 0.034 Uiso 1 1 calc R . . C18 C 0.7458(3) -0.0190(3) 0.88211(18) 0.0254(9) Uani 1 1 d . . . H18 H 0.7967 0.0208 0.9116 0.030 Uiso 1 1 calc R . . C19 C 0.6256(3) 0.0038(3) 0.97319(19) 0.0276(9) Uani 1 1 d . . . C20 C 0.5136(3) 0.0085(3) 0.99328(18) 0.0255(9) Uani 1 1 d . . . C21 C 0.4326(3) -0.0008(3) 0.94489(19) 0.0292(9) Uani 1 1 d . . . H21 H 0.4491 -0.0061 0.8969 0.035 Uiso 1 1 calc R . . C22 C 0.3278(3) -0.0023(3) 0.96624(19) 0.0324(9) Uani 1 1 d . . . H22 H 0.2719 -0.0078 0.9335 0.039 Uiso 1 1 calc R . . C23 C 0.3071(3) 0.0044(3) 1.03645(19) 0.0273(9) Uani 1 1 d . . . C24 C 0.3858(3) 0.0169(3) 1.0856(2) 0.0303(9) Uani 1 1 d . . . H24 H 0.3687 0.0231 1.1335 0.036 Uiso 1 1 calc R . . C25 C 0.4900(3) 0.0201(3) 1.06374(19) 0.0282(9) Uani 1 1 d . . . H25 H 0.5453 0.0302 1.0965 0.034 Uiso 1 1 calc R . . C26 C 0.7641(3) -0.1337(3) 0.89266(19) 0.0280(9) Uani 1 1 d . . . C27 C 0.8907(4) -0.2667(3) 0.8825(2) 0.0491(13) Uani 1 1 d . . . H27A H 0.8450 -0.3075 0.8519 0.074 Uiso 1 1 calc R . . H27B H 0.8805 -0.2891 0.9307 0.074 Uiso 1 1 calc R . . H27C H 0.9649 -0.2770 0.8693 0.074 Uiso 1 1 calc R . . C28 C 0.8007(3) 0.4150(3) 0.70477(18) 0.0255(9) Uani 1 1 d . . . C29 C 0.7224(3) 0.4829(3) 0.72542(19) 0.0306(9) Uani 1 1 d . . . H29 H 0.6637 0.4586 0.7516 0.037 Uiso 1 1 calc R . . C30 C 0.7299(3) 0.5866(3) 0.7078(2) 0.0351(10) Uani 1 1 d . . . H30 H 0.6768 0.6338 0.7226 0.042 Uiso 1 1 calc R . . C31 C 0.8149(3) 0.6215(3) 0.6685(2) 0.0336(10) Uani 1 1 d . . . H31 H 0.8206 0.6927 0.6570 0.040 Uiso 1 1 calc R . . C32 C 0.8901(3) 0.5535(3) 0.6464(2) 0.0315(10) Uani 1 1 d . . . H32 H 0.9468 0.5773 0.6182 0.038 Uiso 1 1 calc R . . C33 C 0.8850(3) 0.4502(3) 0.66456(19) 0.0273(9) Uani 1 1 d . . . H33 H 0.9386 0.4036 0.6497 0.033 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 O1 0.0202(13) 0.0317(15) 0.0311(14) -0.0038(12) -0.0039(11) 0.0008(12) O2 0.0299(15) 0.0246(14) 0.0174(13) 0.0004(11) -0.0035(11) 0.0003(12) O3 0.0296(15) 0.0267(14) 0.0258(14) 0.0007(12) -0.0012(12) -0.0009(12) O4 0.0231(14) 0.0288(15) 0.0347(16) 0.0097(12) 0.0010(12) 0.0050(12) O5 0.0252(14) 0.0285(15) 0.0211(13) -0.0037(11) 0.0002(11) -0.0060(12) O6 0.0231(16) 0.0441(17) 0.0355(16) -0.0042(14) 0.0049(12) 0.0009(13) O7 0.057(2) 0.0390(18) 0.0261(16) -0.0049(14) -0.0095(14) 0.0079(15) O8 0.0364(18) 0.067(2) 0.0493(19) -0.0026(17) -0.0057(15) -0.0199(17) O9 0.0241(14) 0.0361(15) 0.0243(14) 0.0017(13) 0.0003(11) 0.0017(12) O10 0.0317(15) 0.0455(18) 0.0253(15) -0.0030(13) -0.0048(12) -0.0003(14) O11 0.0331(17) 0.065(2) 0.0442(18) 0.0057(17) 0.0023(15) 0.0040(17) O12 0.0451(18) 0.056(2) 0.0295(17) -0.0031(14) 0.0099(14) -0.0024(16) O13 0.0353(17) 0.0313(16) 0.0454(17) 0.0044(14) 0.0033(14) -0.0061(14) O14 0.0300(16) 0.0244(15) 0.0527(18) 0.0119(13) 0.0135(14) 0.0086(13) N1 0.054(2) 0.027(2) 0.030(2) -0.0026(17) -0.0128(18) -0.0008(18) N2 0.041(2) 0.0260(19) 0.035(2) -0.0029(17) 0.0020(17) 0.0035(17) C1 0.020(2) 0.038(3) 0.040(2) -0.011(2) -0.0024(18) 0.0000(18) C2 0.037(2) 0.038(3) 0.028(2) -0.006(2) -0.0073(19) 0.000(2) C3 0.039(2) 0.032(2) 0.025(2) -0.0027(18) -0.0023(19) 0.003(2) C4 0.028(2) 0.029(2) 0.024(2) 0.0037(17) 0.0027(17) 0.0029(18) C5 0.023(2) 0.023(2) 0.025(2) 0.0070(17) 0.0028(16) 0.0018(16) C6 0.022(2) 0.032(2) 0.022(2) 0.0064(17) 0.0021(16) 0.0038(17) C7 0.026(2) 0.027(2) 0.043(3) 0.0167(19) -0.0089(19) 0.0001(18) C8 0.028(2) 0.022(2) 0.030(2) 0.0028(17) -0.0053(17) 0.0005(18) C9 0.029(2) 0.024(2) 0.0182(19) 0.0014(16) 0.0016(16) -0.0006(16) C10 0.0228(19) 0.022(2) 0.031(2) -0.0003(17) -0.0023(16) -0.0019(17) C11 0.026(2) 0.024(2) 0.024(2) 0.0016(17) -0.0006(17) 0.0024(17) C12 0.027(2) 0.019(2) 0.026(2) 0.0024(16) -0.0011(17) 0.0036(17) C13 0.030(2) 0.028(2) 0.025(2) 0.0006(18) 0.0051(18) 0.0035(18) C14 0.039(3) 0.029(2) 0.027(2) 0.0017(18) -0.0014(18) 0.002(2) C15 0.034(2) 0.021(2) 0.024(2) 0.0039(17) -0.0060(17) 0.0010(18) C16 0.029(2) 0.028(2) 0.030(2) 0.0008(18) 0.0017(18) -0.0021(18) C17 0.032(2) 0.025(2) 0.029(2) -0.0003(18) 0.0028(18) 0.0039(18) C18 0.020(2) 0.028(2) 0.029(2) 0.0019(17) -0.0010(16) -0.0024(17) C19 0.038(2) 0.019(2) 0.026(2) -0.0032(18) -0.0037(18) 0.0028(19) C20 0.029(2) 0.021(2) 0.027(2) 0.0006(18) 0.0011(16) -0.0014(18) C21 0.032(2) 0.030(2) 0.025(2) -0.0058(19) 0.0006(17) 0.0026(19) C22 0.033(2) 0.034(2) 0.030(2) 0.001(2) -0.0003(18) 0.007(2) C23 0.027(2) 0.023(2) 0.032(2) 0.0007(18) 0.0057(17) 0.0055(18) C24 0.038(2) 0.028(2) 0.025(2) -0.0036(18) 0.0011(18) -0.003(2) C25 0.035(2) 0.026(2) 0.023(2) -0.0024(18) -0.0052(17) -0.0002(19) C26 0.025(2) 0.030(2) 0.028(2) 0.0020(18) -0.0013(18) -0.0005(19) C27 0.055(3) 0.025(2) 0.067(3) 0.012(2) 0.021(3) 0.012(2) C28 0.027(2) 0.023(2) 0.026(2) 0.0021(17) -0.0048(17) -0.0032(17) C29 0.030(2) 0.028(2) 0.034(2) 0.0032(18) -0.0019(18) -0.0016(18) C30 0.041(3) 0.026(2) 0.038(2) -0.0017(19) -0.004(2) 0.0016(19) C31 0.039(2) 0.022(2) 0.040(3) 0.0035(18) -0.010(2) -0.002(2) C32 0.031(2) 0.030(2) 0.033(2) 0.0007(19) -0.0063(19) -0.0043(19) C33 0.024(2) 0.028(2) 0.030(2) -0.0011(17) -0.0013(17) -0.0012(18) _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 O1 C5 1.405(4) . ? O1 C1 1.453(4) . ? O2 C9 1.423(4) . ? O2 C5 1.436(4) . ? O3 C6 1.422(4) . ? O3 C8 1.441(4) . ? O4 C6 1.417(4) . ? O4 C7 1.429(4) . ? O5 C11 1.364(4) . ? O5 C10 1.445(4) . ? O6 C11 1.195(4) . ? O7 N1 1.222(4) . ? O8 N1 1.222(4) . ? O9 C19 1.357(4) . ? O9 C18 1.428(4) . ? O10 C19 1.201(4) . ? O11 N2 1.220(4) . ? O12 N2 1.231(4) . ? O13 C26 1.188(4) . ? O14 C26 1.332(4) . ? O14 C27 1.461(4) . ? N1 C15 1.465(5) . ? N2 C23 1.460(5) . ? C1 C2 1.504(5) . ? C2 C3 1.509(5) . ? C3 C4 1.530(5) . ? C4 C5 1.514(5) . ? C5 C6 1.538(5) . ? C6 C28 1.503(5) . ? C7 C8 1.510(5) . ? C8 C9 1.524(5) . ? C9 C10 1.531(5) . ? C10 C18 1.498(5) . ? C11 C12 1.472(5) . ? C12 C13 1.376(5) . ? C12 C17 1.388(5) . ? C13 C14 1.374(5) . ? C14 C15 1.377(5) . ? C15 C16 1.383(5) . ? C16 C17 1.387(5) . ? C18 C26 1.516(5) . ? C19 C20 1.468(5) . ? C20 C21 1.389(5) . ? C20 C25 1.397(5) . ? C21 C22 1.385(5) . ? C22 C23 1.379(5) . ? C23 C24 1.382(5) . ? C24 C25 1.382(5) . ? C28 C29 1.381(5) . ? C28 C33 1.392(5) . ? C29 C30 1.388(5) . ? C30 C31 1.389(5) . ? C31 C32 1.363(5) . ? C32 C33 1.383(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 C5 O1 C1 113.9(3) . . ? C9 O2 C5 114.8(3) . . ? C6 O3 C8 101.6(3) . . ? C6 O4 C7 107.7(3) . . ? C11 O5 C10 116.1(3) . . ? C19 O9 C18 114.2(3) . . ? C26 O14 C27 115.1(3) . . ? O8 N1 O7 123.3(3) . . ? O8 N1 C15 118.9(3) . . ? O7 N1 C15 117.8(4) . . ? O11 N2 O12 124.2(4) . . ? O11 N2 C23 118.2(3) . . ? O12 N2 C23 117.5(3) . . ? O1 C1 C2 111.3(3) . . ? C1 C2 C3 109.6(3) . . ? C2 C3 C4 109.8(3) . . ? C5 C4 C3 110.9(3) . . ? O1 C5 O2 110.9(3) . . ? O1 C5 C4 112.6(3) . . ? O2 C5 C4 105.2(3) . . ? O1 C5 C6 106.1(3) . . ? O2 C5 C6 107.9(3) . . ? C4 C5 C6 114.2(3) . . ? O4 C6 O3 105.1(3) . . ? O4 C6 C28 109.7(3) . . ? O3 C6 C28 108.4(3) . . ? O4 C6 C5 107.5(3) . . ? O3 C6 C5 108.6(3) . . ? C28 C6 C5 117.0(3) . . ? O4 C7 C8 103.5(3) . . ? O3 C8 C7 101.5(3) . . ? O3 C8 C9 106.1(3) . . ? C7 C8 C9 113.4(3) . . ? O2 C9 C8 107.9(3) . . ? O2 C9 C10 105.3(3) . . ? C8 C9 C10 113.2(3) . . ? O5 C10 C18 107.9(3) . . ? O5 C10 C9 106.8(3) . . ? C18 C10 C9 114.2(3) . . ? O6 C11 O5 123.8(3) . . ? O6 C11 C12 124.9(3) . . ? O5 C11 C12 111.2(3) . . ? C13 C12 C17 120.2(3) . . ? C13 C12 C11 117.7(3) . . ? C17 C12 C11 122.1(3) . . ? C12 C13 C14 120.6(4) . . ? C13 C14 C15 118.3(4) . . ? C14 C15 C16 123.1(4) . . ? C14 C15 N1 119.5(4) . . ? C16 C15 N1 117.4(3) . . ? C15 C16 C17 117.4(4) . . ? C16 C17 C12 120.4(4) . . ? O9 C18 C10 109.9(3) . . ? O9 C18 C26 108.1(3) . . ? C10 C18 C26 111.1(3) . . ? O10 C19 O9 122.3(4) . . ? O10 C19 C20 124.6(3) . . ? O9 C19 C20 113.0(3) . . ? C21 C20 C25 120.2(3) . . ? C21 C20 C19 122.0(3) . . ? C25 C20 C19 117.8(3) . . ? C22 C21 C20 120.4(3) . . ? C23 C22 C21 118.1(4) . . ? C22 C23 C24 122.8(4) . . ? C22 C23 N2 118.0(3) . . ? C24 C23 N2 119.1(3) . . ? C25 C24 C23 118.6(4) . . ? C24 C25 C20 119.7(4) . . ? O13 C26 O14 125.4(4) . . ? O13 C26 C18 124.9(3) . . ? O14 C26 C18 109.7(3) . . ? C29 C28 C33 120.0(3) . . ? C29 C28 C6 120.5(3) . . ? C33 C28 C6 119.4(3) . . ? C28 C29 C30 119.7(4) . . ? C29 C30 C31 120.0(4) . . ? C32 C31 C30 119.9(4) . . ? C31 C32 C33 120.8(4) . . ? C32 C33 C28 119.5(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.204 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.051 data_9939=8 _database_code_depnum_ccdc_archive 'CCDC 257572' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 O4' _chemical_formula_weight 261.29 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 15.354(4) _cell_length_b 6.0880(9) _cell_length_c 14.926(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.236(17) _cell_angle_gamma 90.00 _cell_volume 1282.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 5.02 _cell_measurement_theta_max 12.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Siemens P4 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 1630 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1464 _reflns_number_gt 1341 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0386P)^2^+0.6617P] 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 SHELXL _refine_ls_extinction_coef 0.0086(11) _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 -0.1(14) _refine_ls_number_reflns 1464 _refine_ls_number_parameters 173 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.002 _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 O1 O 0.01813(10) 0.2468(3) 0.59656(10) 0.0293(4) Uani 1 1 d . . . O2 O 0.18276(11) 0.5018(3) 0.68304(11) 0.0333(5) Uani 1 1 d . . . O3 O 0.20948(12) 0.1497(4) 0.65301(11) 0.0406(5) Uani 1 1 d . . . O4 O 0.05039(10) 0.3709(3) 0.75487(11) 0.0280(4) Uani 1 1 d . . . C1 C 0.03164(15) 0.4488(5) 0.55449(15) 0.0300(6) Uani 1 1 d . . . H1A H 0.0114 0.5696 0.5852 0.036 Uiso 1 1 calc R . . C2 C 0.13701(16) 0.4761(6) 0.57850(16) 0.0375(7) Uani 1 1 d . . . H2A H 0.1492 0.6022 0.5443 0.045 Uiso 1 1 calc R . . C3 C 0.18500(17) 0.2699(7) 0.56327(16) 0.0466(9) Uani 1 1 d . . . H3A H 0.1422 0.1855 0.5084 0.056 Uiso 1 1 calc R . . H3B H 0.2412 0.3062 0.5517 0.056 Uiso 1 1 calc R . . C4 C 0.18112(16) 0.2835(5) 0.71515(16) 0.0298(6) Uani 1 1 d . . . C5 C 0.07739(15) 0.2217(5) 0.69846(15) 0.0264(6) Uani 1 1 d . . . C6 C -0.04464(16) 0.3370(5) 0.74873(19) 0.0347(7) Uani 1 1 d . . . H6A H -0.0891 0.3682 0.6828 0.042 Uiso 1 1 calc R . . H6B H -0.0571 0.4396 0.7920 0.042 Uiso 1 1 calc R . . C7 C -0.06100(18) 0.1077(5) 0.7753(2) 0.0424(7) Uani 1 1 d . . . H7A H -0.1271 0.0899 0.7648 0.051 Uiso 1 1 calc R . . H7B H -0.0228 0.0817 0.8437 0.051 Uiso 1 1 calc R . . C8 C -0.03508(17) -0.0584(5) 0.7136(2) 0.0402(7) Uani 1 1 d . . . H8A H -0.0788 -0.0460 0.6459 0.048 Uiso 1 1 calc R . . H8B H -0.0395 -0.2062 0.7357 0.048 Uiso 1 1 calc R . . C9 C 0.06575(16) -0.0141(5) 0.72263(18) 0.0340(6) Uani 1 1 d . . . H9A H 0.1099 -0.0460 0.7887 0.041 Uiso 1 1 calc R . . H9B H 0.0805 -0.1104 0.6788 0.041 Uiso 1 1 calc R . . C10 C 0.25080(15) 0.2611(5) 0.82024(16) 0.0295(6) Uani 1 1 d . . . C11 C 0.30135(16) 0.0672(5) 0.85170(18) 0.0362(7) Uani 1 1 d . . . H11A H 0.2922 -0.0495 0.8087 0.043 Uiso 1 1 calc R . . C12 C 0.36595(18) 0.0488(6) 0.94840(19) 0.0444(8) Uani 1 1 d . . . H12A H 0.4002 -0.0805 0.9697 0.053 Uiso 1 1 calc R . . C13 C 0.37925(17) 0.2198(6) 1.01225(18) 0.0448(8) Uani 1 1 d . . . H13A H 0.4228 0.2065 1.0764 0.054 Uiso 1 1 calc R . . C14 C 0.32806(18) 0.4122(6) 0.98158(18) 0.0413(7) Uani 1 1 d . . . H14A H 0.3365 0.5273 1.0252 0.050 Uiso 1 1 calc R . . C15 C 0.26377(16) 0.4328(5) 0.88510(17) 0.0344(6) Uani 1 1 d . . . H15A H 0.2295 0.5621 0.8642 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 O1 0.0264(8) 0.0352(10) 0.0233(8) -0.0011(8) 0.0066(6) -0.0037(8) O2 0.0285(8) 0.0431(13) 0.0257(8) 0.0015(9) 0.0080(7) -0.0085(9) O3 0.0337(9) 0.0602(15) 0.0293(9) -0.0061(10) 0.0139(7) 0.0076(10) O4 0.0262(8) 0.0303(10) 0.0304(8) -0.0047(8) 0.0142(7) -0.0018(8) C1 0.0293(11) 0.0359(16) 0.0252(12) -0.0001(12) 0.0113(10) -0.0004(12) C2 0.0319(12) 0.057(2) 0.0236(11) 0.0052(14) 0.0105(10) -0.0069(14) C3 0.0311(12) 0.085(3) 0.0275(12) -0.0034(16) 0.0152(10) 0.0021(17) C4 0.0269(11) 0.0379(17) 0.0268(11) -0.0047(12) 0.0129(9) 0.0006(12) C5 0.0251(11) 0.0315(15) 0.0207(10) 0.0000(11) 0.0069(8) 0.0023(11) C6 0.0278(12) 0.0413(18) 0.0402(14) 0.0003(13) 0.0189(10) 0.0005(12) C7 0.0330(14) 0.0480(19) 0.0509(16) 0.0076(16) 0.0215(12) -0.0069(14) C8 0.0394(13) 0.0267(15) 0.0480(15) 0.0058(13) 0.0103(12) -0.0057(13) C9 0.0328(12) 0.0312(15) 0.0319(13) -0.0012(13) 0.0063(10) 0.0029(13) C10 0.0210(11) 0.0416(16) 0.0269(11) -0.0004(13) 0.0104(9) 0.0001(13) C11 0.0265(12) 0.0464(19) 0.0359(13) -0.0038(14) 0.0125(10) 0.0017(13) C12 0.0306(13) 0.054(2) 0.0428(15) 0.0080(16) 0.0088(11) 0.0075(14) C13 0.0321(13) 0.065(2) 0.0300(13) 0.0052(16) 0.0043(10) -0.0008(15) C14 0.0405(13) 0.051(2) 0.0290(12) -0.0071(14) 0.0107(11) -0.0055(15) C15 0.0314(12) 0.0409(17) 0.0303(12) -0.0016(13) 0.0114(10) 0.0018(13) _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 O1 C1 1.432(3) . ? O1 C5 1.440(2) . ? O2 C4 1.416(4) . ? O2 C2 1.445(3) . ? O3 C4 1.425(3) . ? O3 C3 1.440(3) . ? O4 C5 1.408(3) . ? O4 C6 1.440(3) . ? C1 C2 1.522(3) . ? C1 C1 1.531(4) 2_556 ? C2 C3 1.517(5) . ? C4 C10 1.516(3) . ? C4 C5 1.558(3) . ? C5 C9 1.508(4) . ? C6 C7 1.499(4) . ? C7 C8 1.522(4) . ? C8 C9 1.524(3) . ? C10 C15 1.385(4) . ? C10 C11 1.389(4) . ? C11 C12 1.396(3) . ? C12 C13 1.371(4) . ? C13 C14 1.384(5) . ? C14 C15 1.394(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 C1 O1 C5 114.45(18) . . ? C4 O2 C2 101.4(2) . . ? C4 O3 C3 106.3(2) . . ? C5 O4 C6 113.56(19) . . ? O1 C1 C2 108.4(2) . . ? O1 C1 C1 108.96(14) . 2_556 ? C2 C1 C1 114.9(2) . 2_556 ? O2 C2 C3 101.2(2) . . ? O2 C2 C1 106.55(17) . . ? C3 C2 C1 114.1(3) . . ? O3 C3 C2 104.17(18) . . ? O2 C4 O3 105.38(18) . . ? O2 C4 C10 109.6(2) . . ? O3 C4 C10 110.5(2) . . ? O2 C4 C5 109.0(2) . . ? O3 C4 C5 108.26(19) . . ? C10 C4 C5 113.78(17) . . ? O4 C5 O1 110.54(19) . . ? O4 C5 C9 112.36(19) . . ? O1 C5 C9 105.6(2) . . ? O4 C5 C4 105.80(19) . . ? O1 C5 C4 108.87(16) . . ? C9 C5 C4 113.7(2) . . ? O4 C6 C7 112.8(2) . . ? C6 C7 C8 110.4(2) . . ? C7 C8 C9 109.1(2) . . ? C5 C9 C8 111.1(2) . . ? C15 C10 C11 119.9(2) . . ? C15 C10 C4 120.2(3) . . ? C11 C10 C4 119.9(2) . . ? C10 C11 C12 119.5(3) . . ? C13 C12 C11 120.5(3) . . ? C12 C13 C14 120.2(2) . . ? C13 C14 C15 119.8(3) . . ? C10 C15 C14 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.151 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.037 data_9964=3 _database_code_depnum_ccdc_archive 'CCDC 257573' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 O4' _chemical_formula_weight 276.32 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' _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 6.320(6) _cell_length_b 23.154(16) _cell_length_c 9.673(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.89(6) _cell_angle_gamma 90.00 _cell_volume 1361.4(18) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.57 _cell_measurement_theta_max 11.58 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(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 'Siemens P4 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <5 _diffrn_reflns_number 4587 _diffrn_reflns_av_R_equivalents 0.0723 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 24.01 _reflns_number_total 2143 _reflns_number_gt 1435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Fait, 1991)' _computing_cell_refinement 'XSCANS (Fait, 1991)' _computing_data_reduction 'XSCANS (Fait, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '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^)+(0.0802P)^2^+0.5128P] 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 0.022(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2143 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0946 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1657 _refine_ls_wR_factor_gt 0.1450 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 O1 O 0.2938(3) 0.17060(11) 0.3537(2) 0.0329(6) Uani 1 1 d . . . O2 O 0.6390(3) 0.19158(10) 0.6026(2) 0.0308(6) Uani 1 1 d . . . O3 O 0.3011(4) 0.21764(10) 0.6381(2) 0.0333(6) Uani 1 1 d . . . O4 O 0.4458(3) 0.08699(10) 0.4763(2) 0.0279(6) Uani 1 1 d . . . C1 C 0.4994(5) 0.19561(18) 0.3453(4) 0.0376(9) Uani 1 1 d . . . H1A H 0.4727 0.2209 0.2623 0.045 Uiso 1 1 calc R . . H1B H 0.5980 0.1651 0.3331 0.045 Uiso 1 1 calc R . . C2 C 0.6071(5) 0.22981(16) 0.4802(4) 0.0360(9) Uani 1 1 d . . . H2A H 0.7519 0.2428 0.4740 0.043 Uiso 1 1 calc R . . C3 C 0.4797(6) 0.28176(18) 0.5054(4) 0.0443(10) Uani 1 1 d . . . H3A H 0.4474 0.3064 0.4211 0.053 Uiso 1 1 calc R . . H3B H 0.5684 0.3037 0.5860 0.053 Uiso 1 1 calc R . . C4 C 0.4329(5) 0.17120(14) 0.6155(3) 0.0259(7) Uani 1 1 d . . . C5 C 0.2667(6) 0.26396(18) 0.5365(4) 0.0425(10) Uani 1 1 d . . . H5A H 0.2050 0.2968 0.5740 0.051 Uiso 1 1 calc R . . H5B H 0.1619 0.2519 0.4478 0.051 Uiso 1 1 calc R . . C6 C 0.3130(5) 0.13667(15) 0.4784(3) 0.0263(8) Uani 1 1 d . . . C7 C 0.3575(5) 0.04984(16) 0.3554(3) 0.0320(8) Uani 1 1 d . . . H7A H 0.4537 0.0168 0.3611 0.038 Uiso 1 1 calc R . . H7B H 0.3532 0.0706 0.2675 0.038 Uiso 1 1 calc R . . C8 C 0.1277(5) 0.02896(17) 0.3497(4) 0.0370(9) Uani 1 1 d . . . H8A H 0.1332 0.0045 0.4321 0.044 Uiso 1 1 calc R . . H8B H 0.0693 0.0063 0.2633 0.044 Uiso 1 1 calc R . . C9 C -0.0218(5) 0.08087(18) 0.3503(4) 0.0386(9) Uani 1 1 d . . . H9A H -0.0434 0.1024 0.2615 0.046 Uiso 1 1 calc R . . H9B H -0.1644 0.0676 0.3568 0.046 Uiso 1 1 calc R . . C10 C 0.0811(5) 0.11952(16) 0.4766(3) 0.0299(8) Uani 1 1 d . . . H10A H 0.0840 0.0995 0.5652 0.036 Uiso 1 1 calc R . . H10B H -0.0079 0.1540 0.4715 0.036 Uiso 1 1 calc R . . C11 C 0.4814(5) 0.13438(15) 0.7505(3) 0.0288(8) Uani 1 1 d . . . C12 C 0.3336(6) 0.13374(17) 0.8330(3) 0.0357(9) Uani 1 1 d . . . H12A H 0.2047 0.1553 0.8049 0.043 Uiso 1 1 calc R . . C13 C 0.3782(6) 0.10082(18) 0.9579(4) 0.0428(10) Uani 1 1 d . . . H13A H 0.2772 0.0998 1.0120 0.051 Uiso 1 1 calc R . . C14 C 0.5700(6) 0.06985(17) 1.0020(4) 0.0425(10) Uani 1 1 d . . . H14A H 0.6005 0.0487 1.0868 0.051 Uiso 1 1 calc R . . C15 C 0.7177(6) 0.07027(17) 0.9199(4) 0.0408(9) Uani 1 1 d . . . H15A H 0.8468 0.0489 0.9488 0.049 Uiso 1 1 calc R . . C16 C 0.6738(5) 0.10255(15) 0.7943(3) 0.0316(8) Uani 1 1 d . . . H16A H 0.7739 0.1028 0.7395 0.038 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 O1 0.0258(11) 0.0457(16) 0.0270(12) 0.0108(11) 0.0068(9) 0.0033(11) O2 0.0238(11) 0.0389(15) 0.0309(12) 0.0081(10) 0.0094(9) -0.0008(10) O3 0.0360(12) 0.0314(14) 0.0376(13) 0.0052(11) 0.0187(10) 0.0057(11) O4 0.0236(11) 0.0384(15) 0.0224(11) 0.0003(10) 0.0073(9) 0.0035(10) C1 0.0309(18) 0.054(3) 0.0336(19) 0.0176(17) 0.0190(15) 0.0062(16) C2 0.0288(17) 0.037(2) 0.044(2) 0.0123(17) 0.0140(15) 0.0010(15) C3 0.038(2) 0.048(3) 0.049(2) 0.011(2) 0.0148(17) 0.0001(18) C4 0.0233(15) 0.0287(19) 0.0278(16) 0.0004(14) 0.0106(13) 0.0007(14) C5 0.042(2) 0.041(2) 0.050(2) 0.0085(18) 0.0223(18) 0.0061(18) C6 0.0241(16) 0.034(2) 0.0225(16) 0.0055(14) 0.0094(13) 0.0060(14) C7 0.0326(17) 0.040(2) 0.0254(16) -0.0028(15) 0.0115(14) 0.0016(16) C8 0.0352(18) 0.042(2) 0.0326(19) -0.0089(17) 0.0082(15) -0.0030(16) C9 0.0232(16) 0.058(3) 0.0347(19) 0.0020(18) 0.0075(14) -0.0034(17) C10 0.0218(15) 0.038(2) 0.0314(18) 0.0006(15) 0.0097(13) 0.0010(14) C11 0.0314(17) 0.033(2) 0.0211(16) -0.0017(14) 0.0058(13) -0.0035(15) C12 0.0395(19) 0.041(2) 0.0300(18) -0.0016(16) 0.0147(15) 0.0009(17) C13 0.051(2) 0.053(3) 0.0277(18) 0.0020(18) 0.0157(17) -0.008(2) C14 0.061(2) 0.042(2) 0.0209(17) 0.0027(16) 0.0059(17) -0.013(2) C15 0.044(2) 0.041(2) 0.0301(18) 0.0020(17) -0.0012(15) -0.0014(18) C16 0.0332(17) 0.032(2) 0.0275(17) 0.0003(15) 0.0048(14) -0.0014(15) _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 O1 C6 1.417(4) . ? O1 C1 1.445(4) . ? O2 C4 1.423(4) . ? O2 C2 1.448(4) . ? O3 C4 1.413(4) . ? O3 C5 1.431(4) . ? O4 C6 1.428(4) . ? O4 C7 1.436(4) . ? C1 C2 1.518(5) . ? C2 C3 1.504(5) . ? C3 C5 1.515(5) . ? C4 C11 1.519(4) . ? C4 C6 1.556(4) . ? C6 C10 1.514(4) . ? C7 C8 1.517(5) . ? C8 C9 1.530(5) . ? C9 C10 1.510(5) . ? C11 C12 1.385(5) . ? C11 C16 1.386(5) . ? C12 C13 1.391(5) . ? C13 C14 1.372(6) . ? C14 C15 1.381(5) . ? C15 C16 1.388(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 C6 O1 C1 113.7(2) . . ? C4 O2 C2 110.4(2) . . ? C4 O3 C5 116.7(2) . . ? C6 O4 C7 113.3(2) . . ? O1 C1 C2 111.0(3) . . ? O2 C2 C3 108.5(3) . . ? O2 C2 C1 108.3(3) . . ? C3 C2 C1 115.0(3) . . ? C2 C3 C5 111.0(3) . . ? O3 C4 O2 110.7(3) . . ? O3 C4 C11 106.4(2) . . ? O2 C4 C11 106.7(2) . . ? O3 C4 C6 110.7(2) . . ? O2 C4 C6 109.9(2) . . ? C11 C4 C6 112.4(3) . . ? O3 C5 C3 111.4(3) . . ? O1 C6 O4 110.4(2) . . ? O1 C6 C10 106.2(3) . . ? O4 C6 C10 111.1(3) . . ? O1 C6 C4 110.4(3) . . ? O4 C6 C4 106.0(2) . . ? C10 C6 C4 112.9(3) . . ? O4 C7 C8 112.0(3) . . ? C7 C8 C9 109.6(3) . . ? C10 C9 C8 109.8(3) . . ? C9 C10 C6 111.5(3) . . ? C12 C11 C16 119.5(3) . . ? C12 C11 C4 119.5(3) . . ? C16 C11 C4 121.0(3) . . ? C11 C12 C13 119.9(3) . . ? C14 C13 C12 120.5(3) . . ? C13 C14 C15 119.8(3) . . ? C14 C15 C16 120.2(4) . . ? C11 C16 C15 120.2(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.275 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.061 data_02013=4' _database_code_depnum_ccdc_archive 'CCDC 257574' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H23 N O8' _chemical_formula_weight 441.42 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' _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 34.238(8) _cell_length_b 6.778(2) _cell_length_c 18.623(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.64(2) _cell_angle_gamma 90.00 _cell_volume 4070(3) _cell_formula_units_Z 8 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 10.70 _cell_measurement_theta_max 24.69 _exptl_crystal_description needle _exptl_crystal_colour biege _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.110 _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 140(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 'siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 4409 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3571 _reflns_number_gt 2530 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0690P)^2^+2.6931P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3571 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1377 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 O1 O 0.09269(5) 0.2111(2) 0.11517(9) 0.0239(4) Uani 1 1 d . . . O2 O 0.14808(5) 0.2822(3) 0.26332(9) 0.0275(4) Uani 1 1 d . . . O3 O 0.16042(5) 0.1385(2) 0.04893(9) 0.0276(4) Uani 1 1 d . . . O4 O 0.06388(5) 0.1596(2) 0.21080(9) 0.0246(4) Uani 1 1 d . . . O5 O 0.13056(5) 0.5550(2) 0.19055(9) 0.0263(4) Uani 1 1 d . . . O7 O 0.16596(7) -0.1094(3) -0.02551(11) 0.0416(5) Uani 1 1 d . . . O9 O 0.25652(6) 0.5411(3) -0.20905(11) 0.0418(5) Uani 1 1 d . . . O15 O 0.25494(7) 0.7688(3) -0.12875(12) 0.0510(6) Uani 1 1 d . . . N1 N 0.24710(7) 0.6001(4) -0.15467(13) 0.0333(6) Uani 1 1 d . . . C6 C 0.07811(7) 0.3037(4) 0.17047(13) 0.0222(5) Uani 1 1 d . . . C8 C 0.19752(8) 0.4013(4) -0.02146(15) 0.0297(6) Uani 1 1 d . . . H8A H 0.1905 0.4439 0.0201 0.036 Uiso 1 1 calc R . . C10 C 0.18927(8) 0.2077(4) -0.04715(14) 0.0249(6) Uani 1 1 d . . . C12 C 0.16197(8) 0.2445(4) 0.19978(14) 0.0271(6) Uani 1 1 d . . . H12A H 0.1901 0.1896 0.2162 0.033 Uiso 1 1 calc R . . C16 C 0.17077(8) 0.0621(4) -0.00861(14) 0.0263(6) Uani 1 1 d . . . C17 C 0.02947(8) 0.0451(4) 0.16317(15) 0.0306(6) Uani 1 1 d . . . H17A H 0.0209 -0.0477 0.1946 0.037 Uiso 1 1 calc R . . H17B H 0.0383 -0.0300 0.1270 0.037 Uiso 1 1 calc R . . C19 C 0.14195(8) 0.0007(4) 0.08718(15) 0.0280(6) Uani 1 1 d . . . H19A H 0.1615 -0.1047 0.1093 0.034 Uiso 1 1 calc R . . H19B H 0.1174 -0.0573 0.0505 0.034 Uiso 1 1 calc R . . C20 C 0.13028(8) 0.1017(4) 0.14874(14) 0.0247(6) Uani 1 1 d . . . H20A H 0.1248 -0.0006 0.1814 0.030 Uiso 1 1 calc R . . C11A C 0.10327(5) 0.5121(2) 0.29429(7) 0.0239(6) Uani 1 1 d G . . C12A C 0.10386(5) 0.40265(17) 0.35777(9) 0.0274(6) Uani 1 1 d G . . H12B H 0.1117 0.2706 0.3616 0.033 Uiso 1 1 calc R . . C13A C 0.09275(5) 0.4905(2) 0.41554(7) 0.0303(6) Uani 1 1 d G . . H13A H 0.0931 0.4173 0.4580 0.036 Uiso 1 1 calc R . . C14A C 0.08105(6) 0.6879(2) 0.40983(8) 0.0305(6) Uani 1 1 d G . . H14A H 0.0736 0.7467 0.4485 0.037 Uiso 1 1 calc R . . C15A C 0.08046(6) 0.79731(17) 0.34635(9) 0.0307(6) Uani 1 1 d G . . H15A H 0.0726 0.9293 0.3425 0.037 Uiso 1 1 calc R . . C16A C 0.09157(5) 0.7094(2) 0.28858(7) 0.0273(6) Uani 1 1 d G . . H16A H 0.0912 0.7826 0.2461 0.033 Uiso 1 1 calc R . . C22 C 0.22608(8) 0.4649(4) -0.11812(14) 0.0284(6) Uani 1 1 d . . . C23 C 0.19882(9) 0.1469(4) -0.11083(15) 0.0334(7) Uani 1 1 d . . . H23A H 0.1926 0.0189 -0.1291 0.040 Uiso 1 1 calc R . . C24 C -0.00690(8) 0.1735(4) 0.12031(16) 0.0342(7) Uani 1 1 d . . . H24A H -0.0176 0.2392 0.1561 0.041 Uiso 1 1 calc R . . H24B H -0.0288 0.0925 0.0867 0.041 Uiso 1 1 calc R . . C25 C 0.21604(8) 0.5298(4) -0.05743(15) 0.0323(6) Uani 1 1 d . . . H25A H 0.2216 0.6592 -0.0405 0.039 Uiso 1 1 calc R . . C26 C 0.00671(8) 0.3270(4) 0.07358(15) 0.0310(6) Uani 1 1 d . . . H26A H 0.0144 0.2622 0.0339 0.037 Uiso 1 1 calc R . . H26B H -0.0160 0.4167 0.0495 0.037 Uiso 1 1 calc R . . C27 C 0.21742(9) 0.2744(4) -0.14689(15) 0.0339(7) Uani 1 1 d . . . H27A H 0.2240 0.2344 -0.1892 0.041 Uiso 1 1 calc R . . C28 C 0.04350(8) 0.4415(4) 0.12574(14) 0.0266(6) Uani 1 1 d . . . H28A H 0.0538 0.5305 0.0955 0.032 Uiso 1 1 calc R . . H28B H 0.0346 0.5202 0.1609 0.032 Uiso 1 1 calc R . . C29 C 0.11484(8) 0.4140(4) 0.23109(13) 0.0239(6) Uani 1 1 d . . . C1A C 0.16021(8) 0.4512(4) 0.16451(15) 0.0300(6) Uani 1 1 d . . . H1AC H 0.1871 0.5148 0.1826 0.036 Uiso 1 1 calc R . . H1B H 0.1508 0.4443 0.1093 0.036 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 O1 0.0227(9) 0.0247(9) 0.0247(9) -0.0021(7) 0.0085(7) -0.0010(8) O2 0.0246(9) 0.0292(10) 0.0277(9) -0.0015(8) 0.0076(8) 0.0078(8) O3 0.0323(10) 0.0249(9) 0.0309(9) -0.0047(8) 0.0178(8) -0.0040(8) O4 0.0249(9) 0.0220(9) 0.0273(9) 0.0059(7) 0.0091(8) -0.0009(8) O5 0.0284(10) 0.0227(9) 0.0335(9) -0.0027(8) 0.0177(8) -0.0032(8) O7 0.0614(14) 0.0245(11) 0.0473(12) -0.0102(9) 0.0293(11) -0.0049(10) O9 0.0450(12) 0.0482(13) 0.0404(11) 0.0073(10) 0.0253(10) 0.0097(11) O15 0.0628(16) 0.0405(13) 0.0573(13) -0.0083(11) 0.0302(12) -0.0160(12) N1 0.0274(12) 0.0401(15) 0.0341(12) 0.0044(11) 0.0126(11) 0.0054(11) C6 0.0225(13) 0.0214(13) 0.0241(12) 0.0030(10) 0.0096(11) 0.0000(11) C8 0.0280(14) 0.0300(14) 0.0344(14) -0.0071(12) 0.0150(12) -0.0020(13) C10 0.0185(13) 0.0272(13) 0.0270(13) -0.0018(11) 0.0051(11) 0.0026(11) C12 0.0205(13) 0.0321(14) 0.0302(14) -0.0047(12) 0.0105(11) 0.0011(12) C16 0.0254(14) 0.0274(14) 0.0254(13) -0.0037(12) 0.0078(11) 0.0017(12) C17 0.0294(15) 0.0265(14) 0.0353(14) 0.0047(12) 0.0103(12) -0.0058(13) C19 0.0303(14) 0.0235(13) 0.0343(14) -0.0028(12) 0.0163(12) -0.0060(12) C20 0.0262(14) 0.0210(13) 0.0289(13) -0.0009(11) 0.0118(11) -0.0001(11) C11A 0.0175(12) 0.0271(14) 0.0249(13) -0.0018(11) 0.0044(10) 0.0010(11) C12A 0.0252(14) 0.0233(13) 0.0317(14) 0.0014(12) 0.0070(11) 0.0005(12) C13A 0.0290(14) 0.0361(15) 0.0253(13) 0.0026(12) 0.0086(12) -0.0040(13) C14A 0.0274(15) 0.0339(15) 0.0321(14) -0.0098(12) 0.0124(12) -0.0022(13) C15A 0.0286(15) 0.0256(14) 0.0399(15) -0.0023(12) 0.0142(12) 0.0045(12) C16A 0.0267(14) 0.0265(14) 0.0303(13) 0.0024(11) 0.0118(11) 0.0015(12) C22 0.0229(14) 0.0332(15) 0.0277(13) 0.0036(12) 0.0068(11) 0.0066(12) C23 0.0414(16) 0.0296(14) 0.0322(14) -0.0005(12) 0.0163(13) 0.0055(14) C24 0.0212(14) 0.0399(16) 0.0400(15) 0.0092(13) 0.0083(12) -0.0024(13) C25 0.0294(15) 0.0309(15) 0.0392(15) -0.0056(13) 0.0153(13) -0.0020(13) C26 0.0224(14) 0.0351(15) 0.0336(14) 0.0084(12) 0.0070(12) 0.0004(13) C27 0.0399(17) 0.0382(16) 0.0280(14) -0.0024(13) 0.0171(13) 0.0067(14) C28 0.0266(14) 0.0254(13) 0.0295(13) 0.0067(11) 0.0116(11) 0.0006(12) C29 0.0233(13) 0.0217(13) 0.0269(13) 0.0023(11) 0.0089(11) 0.0046(11) C1A 0.0274(14) 0.0301(14) 0.0348(14) -0.0072(12) 0.0136(12) -0.0047(13) _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 O1 C6 1.431(3) . ? O1 C20 1.434(3) . ? O2 C29 1.412(3) . ? O2 C12 1.439(3) . ? O3 C16 1.341(3) . ? O3 C19 1.443(3) . ? O4 C6 1.415(3) . ? O4 C17 1.441(3) . ? O5 C29 1.431(3) . ? O5 C1A 1.446(3) . ? O7 C16 1.201(3) . ? O9 N1 1.228(3) . ? O15 N1 1.235(3) . ? N1 C22 1.466(3) . ? C6 C28 1.519(3) . ? C6 C29 1.568(3) . ? C8 C25 1.376(4) . ? C8 C10 1.393(4) . ? C10 C23 1.394(4) . ? C10 C16 1.482(4) . ? C12 C20 1.525(3) . ? C12 C1A 1.540(4) . ? C17 C24 1.509(4) . ? C19 C20 1.500(3) . ? C11A C12A 1.3900 . ? C11A C16A 1.3900 . ? C11A C29 1.516(3) . ? C12A C13A 1.3900 . ? C13A C14A 1.3900 . ? C14A C15A 1.3900 . ? C15A C16A 1.3900 . ? C22 C25 1.360(4) . ? C22 C27 1.392(4) . ? C23 C27 1.375(4) . ? C24 C26 1.526(4) . ? C26 C28 1.520(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 C6 O1 C20 113.07(17) . . ? C29 O2 C12 101.83(18) . . ? C16 O3 C19 114.95(19) . . ? C6 O4 C17 113.67(18) . . ? C29 O5 C1A 106.44(19) . . ? O9 N1 O15 122.7(2) . . ? O9 N1 C22 119.0(2) . . ? O15 N1 C22 118.2(2) . . ? O4 C6 O1 110.17(19) . . ? O4 C6 C28 111.8(2) . . ? O1 C6 C28 105.75(19) . . ? O4 C6 C29 106.42(18) . . ? O1 C6 C29 109.75(19) . . ? C28 C6 C29 113.0(2) . . ? C25 C8 C10 120.2(2) . . ? C8 C10 C23 119.5(2) . . ? C8 C10 C16 122.1(2) . . ? C23 C10 C16 118.4(2) . . ? O2 C12 C20 105.2(2) . . ? O2 C12 C1A 102.26(19) . . ? C20 C12 C1A 113.2(2) . . ? O7 C16 O3 122.2(2) . . ? O7 C16 C10 124.1(2) . . ? O3 C16 C10 113.6(2) . . ? O4 C17 C24 111.9(2) . . ? O3 C19 C20 110.8(2) . . ? O1 C20 C19 109.5(2) . . ? O1 C20 C12 106.9(2) . . ? C19 C20 C12 116.7(2) . . ? C12A C11A C16A 120.0 . . ? C12A C11A C29 119.57(13) . . ? C16A C11A C29 120.43(13) . . ? C13A C12A C11A 120.0 . . ? C12A C13A C14A 120.0 . . ? C13A C14A C15A 120.0 . . ? C16A C15A C14A 120.0 . . ? C15A C16A C11A 120.0 . . ? C25 C22 C27 122.6(3) . . ? C25 C22 N1 119.0(2) . . ? C27 C22 N1 118.4(2) . . ? C27 C23 C10 120.6(3) . . ? C17 C24 C26 109.8(2) . . ? C22 C25 C8 119.1(3) . . ? C28 C26 C24 109.3(2) . . ? C23 C27 C22 118.0(2) . . ? C6 C28 C26 111.3(2) . . ? O2 C29 O5 104.73(19) . . ? O2 C29 C11A 109.33(18) . . ? O5 C29 C11A 111.08(19) . . ? O2 C29 C6 109.94(19) . . ? O5 C29 C6 106.94(18) . . ? C11A C29 C6 114.37(19) . . ? O5 C1A C12 103.36(19) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.321 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.052