data_fleu _audit_creation_method SHELXL-97 _chemical_name_systematic ; ((R,S)-5-hydroxy-2-morpholino-3-spiro-1'-cyclohexyl-2,3- dihydro-1,4-benzodioxin-6-yl)carboxylic methyl ester :[3h] ; _chemical_name_common 'Fly051' _chemical_melting_point 468(2) _chemical_formula_moiety 'C19 H25 N O6' _chemical_formula_sum 'C19 H25 N O6' _chemical_formula_weight 363.40 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' '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' 'H' 'H' 0.0000 0.0000 '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 11.468(3) _cell_length_b 12.662(4) _cell_length_c 13.310(4) _cell_angle_alpha 76.23(2) _cell_angle_beta 80.61(2) _cell_angle_gamma 89.87(2) _cell_volume 1850.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7821 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 28529/13476 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8462 _reflns_number_gt 5713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'R3M (Riche, 1983) ORTEP (Johnson, 1965)' _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^)+(0.0490P)^2^+0.2869P] 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 0.014(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 8462 _refine_ls_number_parameters 478 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.60905(8) 0.11267(8) 0.31787(8) 0.0477(3) Uani 1 1 d . . . C2 C 0.62946(12) 0.22029(12) 0.24323(11) 0.0424(3) Uani 1 1 d . . . H2 H 0.5507 0.2476 0.2350 0.049 Uiso 1 1 calc R . . C3 C 0.68685(12) 0.20690(12) 0.13471(11) 0.0435(3) Uani 1 1 d . . . O4 O 0.79501(8) 0.14704(8) 0.14331(7) 0.0433(2) Uani 1 1 d . . . C4a C 0.78150(12) 0.05294(11) 0.22105(11) 0.0386(3) Uani 1 1 d . . . C5 C 0.86378(11) -0.02690(11) 0.21286(11) 0.0389(3) Uani 1 1 d . . . C6 C 0.85618(12) -0.12319(11) 0.29254(11) 0.0409(3) Uani 1 1 d . . . C7 C 0.76425(13) -0.13742(12) 0.37848(11) 0.0466(4) Uani 1 1 d . . . H7 H 0.7581 -0.2012 0.4312 0.054 Uiso 1 1 calc R . . C8 C 0.68304(13) -0.05875(12) 0.38610(12) 0.0464(3) Uani 1 1 d . . . H8 H 0.6223 -0.0694 0.4435 0.053 Uiso 1 1 calc R . . C8a C 0.69215(12) 0.03696(11) 0.30757(11) 0.0404(3) Uani 1 1 d . . . O9 O 0.94805(9) -0.00544(9) 0.12618(9) 0.0521(3) Uani 1 1 d . . . HOH H 0.9938(15) -0.0620(15) 0.1339(13) 0.063 Uiso 1 1 d . . . C10 C 0.94596(14) -0.20411(12) 0.28279(12) 0.0464(4) Uani 1 1 d . . . O11 O 1.03036(10) -0.19141(9) 0.21197(9) 0.0573(3) Uani 1 1 d . . . O12 O 0.92830(11) -0.29459(9) 0.35974(9) 0.0668(3) Uani 1 1 d . . . C13 C 1.0148(2) -0.37733(15) 0.35451(17) 0.0820(6) Uani 1 1 d . . . H13a H 1.0291 -0.3891 0.2850 0.098 Uiso 1 1 calc R . . H13B H 0.9855 -0.4439 0.4039 0.098 Uiso 1 1 calc R . . H13C H 1.0873 -0.3539 0.3712 0.098 Uiso 1 1 calc R . . N14 N 0.68564(10) 0.29728(10) 0.28351(9) 0.0444(3) Uani 1 1 d . . . C15 C 0.80550(13) 0.27624(14) 0.30628(14) 0.0543(4) Uani 1 1 d . . . H15A H 0.8556 0.2603 0.2460 0.062 Uiso 1 1 calc R . . H15B H 0.8036 0.2138 0.3653 0.062 Uiso 1 1 calc R . . C16 C 0.85451(16) 0.37514(16) 0.33163(16) 0.0701(5) Uani 1 1 d . . . H16A H 0.9339 0.3614 0.3466 0.081 Uiso 1 1 calc R . . H16B H 0.8598 0.4360 0.2708 0.081 Uiso 1 1 calc R . . O17 O 0.78441(11) 0.40342(11) 0.41838(10) 0.0724(4) Uani 1 1 d . . . C18 C 0.66815(16) 0.42253(15) 0.39656(15) 0.0660(5) Uani 1 1 d . . . H18A H 0.6705 0.4835 0.3362 0.076 Uiso 1 1 calc R . . H18B H 0.6195 0.4415 0.4560 0.076 Uiso 1 1 calc R . . C19 C 0.61356(14) 0.32406(14) 0.37484(12) 0.0540(4) Uani 1 1 d . . . H19A H 0.6094 0.2630 0.4354 0.062 Uiso 1 1 calc R . . H19B H 0.5338 0.3389 0.3613 0.062 Uiso 1 1 calc R . . C20 C 0.72497(15) 0.31551(13) 0.05874(12) 0.0542(4) Uani 1 1 d . . . H20A H 0.7842 0.3510 0.0851 0.062 Uiso 1 1 calc R . . H20B H 0.6574 0.3617 0.0548 0.062 Uiso 1 1 calc R . . C21 C 0.77555(17) 0.30328(16) -0.05085(13) 0.0677(5) Uani 1 1 d . . . H21A H 0.7920 0.3749 -0.0979 0.078 Uiso 1 1 calc R . . H21B H 0.8496 0.2663 -0.0489 0.078 Uiso 1 1 calc R . . C22 C 0.69117(19) 0.2397(2) -0.09273(14) 0.0814(6) Uani 1 1 d . . . H22A H 0.6209 0.2810 -0.1030 0.094 Uiso 1 1 calc R . . H22B H 0.7285 0.2291 -0.1603 0.094 Uiso 1 1 calc R . . C23 C 0.65614(17) 0.13030(18) -0.01816(14) 0.0715(5) Uani 1 1 d . . . H23A H 0.7253 0.0863 -0.0132 0.082 Uiso 1 1 calc R . . H23B H 0.5991 0.0929 -0.0452 0.082 Uiso 1 1 calc R . . C24 C 0.60247(14) 0.14337(14) 0.09052(13) 0.0550(4) Uani 1 1 d . . . H24A H 0.5842 0.0720 0.1376 0.063 Uiso 1 1 calc R . . H24B H 0.5292 0.1813 0.0865 0.063 Uiso 1 1 calc R . . O1' O 0.11139(8) 0.23468(9) 0.31469(8) 0.0501(3) Uani 1 1 d . . . C2' C 0.12879(12) 0.16087(12) 0.24330(11) 0.0440(3) Uani 1 1 d . . . H2' H 0.0492 0.1373 0.2379 0.051 Uiso 1 1 calc R . . C3' C 0.18329(12) 0.22440(12) 0.13267(11) 0.0434(3) Uani 1 1 d . . . O4' O 0.29344(8) 0.27991(8) 0.13656(7) 0.0417(2) Uani 1 1 d . . . C4a' C 0.28288(11) 0.33899(11) 0.21124(10) 0.0368(3) Uani 1 1 d . . . C5' C 0.36638(11) 0.42319(11) 0.19822(10) 0.0368(3) Uani 1 1 d . . . C6' C 0.36149(12) 0.48333(11) 0.27487(11) 0.0390(3) Uani 1 1 d . . . C7' C 0.27142(13) 0.45837(12) 0.36236(11) 0.0446(3) Uani 1 1 d . . . H7' H 0.2672 0.4984 0.4130 0.051 Uiso 1 1 calc R . . C8' C 0.18934(13) 0.37597(12) 0.37460(11) 0.0453(3) Uani 1 1 d . . . H8' H 0.1297 0.3605 0.4330 0.052 Uiso 1 1 calc R . . C8a' C 0.19548(12) 0.31541(11) 0.29916(11) 0.0400(3) Uani 1 1 d . . . O9' O 0.44882(9) 0.44117(9) 0.11051(8) 0.0491(3) Uani 1 1 d . . . HOH' H 0.4936(15) 0.4950(14) 0.1168(13) 0.059 Uiso 1 1 d . . . C10' C 0.45242(13) 0.56888(12) 0.26049(12) 0.0448(3) Uani 1 1 d . . . O11' O 0.53530(10) 0.58915(9) 0.18810(9) 0.0574(3) Uani 1 1 d . . . O12' O 0.43751(10) 0.62350(9) 0.33535(9) 0.0638(3) Uani 1 1 d . . . C13' C 0.52368(19) 0.71010(16) 0.32531(17) 0.0803(6) Uani 1 1 d . . . H13D H 0.5990 0.6797 0.3347 0.096 Uiso 1 1 calc R . . H13E H 0.4989 0.7498 0.3777 0.096 Uiso 1 1 calc R . . H13F H 0.5304 0.7583 0.2568 0.096 Uiso 1 1 calc R . . N14' N 0.18504(10) 0.06434(10) 0.28602(9) 0.0463(3) Uani 1 1 d . . . C15' C 0.30615(14) 0.07461(13) 0.30538(14) 0.0569(4) Uani 1 1 d . . . H15C H 0.3064 0.1100 0.3625 0.065 Uiso 1 1 calc R . . H15D H 0.3550 0.1187 0.2432 0.065 Uiso 1 1 calc R . . C16' C 0.35508(18) -0.03664(15) 0.33311(18) 0.0784(6) Uani 1 1 d . . . H16C H 0.3585 -0.0696 0.2740 0.090 Uiso 1 1 calc R . . H16D H 0.4351 -0.0299 0.3463 0.090 Uiso 1 1 calc R . . O17' O 0.28619(13) -0.10524(11) 0.42239(12) 0.0891(5) Uani 1 1 d . . . C18' C 0.16925(19) -0.11492(17) 0.40362(17) 0.0849(7) Uani 1 1 d . . . H18C H 0.1217 -0.1616 0.4650 0.098 Uiso 1 1 calc R . . H18D H 0.1699 -0.1485 0.3452 0.098 Uiso 1 1 calc R . . C19' C 0.11491(15) -0.00574(15) 0.37918(13) 0.0638(5) Uani 1 1 d . . . H19C H 0.0347 -0.0144 0.3672 0.073 Uiso 1 1 calc R . . H19D H 0.1119 0.0273 0.4382 0.073 Uiso 1 1 calc R . . C20' C 0.21794(15) 0.14923(13) 0.06007(12) 0.0535(4) Uani 1 1 d . . . H20C H 0.1494 0.1047 0.0597 0.062 Uiso 1 1 calc R . . H20D H 0.2777 0.1011 0.0866 0.062 Uiso 1 1 calc R . . C21' C 0.26590(17) 0.21230(15) -0.05193(13) 0.0654(5) Uani 1 1 d . . . H21C H 0.3409 0.2482 -0.0532 0.075 Uiso 1 1 calc R . . H21D H 0.2799 0.1618 -0.0968 0.075 Uiso 1 1 calc R . . C22' C 0.18126(19) 0.29626(19) -0.09427(14) 0.0796(6) Uani 1 1 d . . . H22C H 0.1097 0.2598 -0.1012 0.092 Uiso 1 1 calc R . . H22D H 0.2171 0.3379 -0.1634 0.092 Uiso 1 1 calc R . . C23' C 0.14979(17) 0.37257(16) -0.02304(14) 0.0702(5) Uani 1 1 d . . . H23C H 0.0924 0.4231 -0.0504 0.081 Uiso 1 1 calc R . . H23D H 0.2200 0.4143 -0.0214 0.081 Uiso 1 1 calc R . . C24' C 0.09855(14) 0.30926(14) 0.08791(12) 0.0556(4) Uani 1 1 d . . . H24C H 0.0243 0.2733 0.0871 0.064 Uiso 1 1 calc R . . H24D H 0.0825 0.3595 0.1329 0.064 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 0.0435(6) 0.0461(6) 0.0492(6) -0.0084(5) -0.0001(4) 0.0091(5) C2 0.0398(8) 0.0436(8) 0.0440(8) -0.0095(6) -0.0094(6) 0.0105(6) C3 0.0405(8) 0.0459(8) 0.0440(8) -0.0103(7) -0.0078(6) 0.0132(6) O4 0.0395(5) 0.0414(6) 0.0452(6) -0.0051(4) -0.0035(4) 0.0085(4) C4a 0.0381(7) 0.0378(7) 0.0406(8) -0.0090(6) -0.0090(6) 0.0029(6) C5 0.0352(7) 0.0406(8) 0.0436(8) -0.0140(6) -0.0082(6) -0.0002(6) C6 0.0419(8) 0.0391(8) 0.0456(8) -0.0135(6) -0.0137(6) 0.0038(6) C7 0.0535(9) 0.0420(8) 0.0437(8) -0.0064(7) -0.0125(7) 0.0008(7) C8 0.0450(8) 0.0494(9) 0.0420(8) -0.0080(7) -0.0036(6) 0.0016(7) C8a 0.0381(7) 0.0421(8) 0.0424(8) -0.0121(6) -0.0083(6) 0.0040(6) O9 0.0456(6) 0.0468(6) 0.0580(7) -0.0096(5) 0.0039(5) 0.0076(5) C10 0.0523(9) 0.0413(8) 0.0520(9) -0.0170(7) -0.0188(8) 0.0065(7) O11 0.0526(7) 0.0521(7) 0.0672(7) -0.0162(6) -0.0075(6) 0.0134(5) O12 0.0855(9) 0.0472(7) 0.0624(7) -0.0063(6) -0.0076(6) 0.0252(6) C13 0.1041(16) 0.0501(11) 0.0880(14) -0.0117(10) -0.0127(12) 0.0358(11) N14 0.0438(7) 0.0471(7) 0.0453(7) -0.0153(6) -0.0099(5) 0.0113(5) C15 0.0445(9) 0.0578(10) 0.0666(10) -0.0226(8) -0.0154(8) 0.0103(7) C16 0.0590(11) 0.0725(12) 0.0911(14) -0.0379(11) -0.0216(10) 0.0071(9) O17 0.0744(8) 0.0816(9) 0.0782(9) -0.0403(7) -0.0306(7) 0.0157(7) C18 0.0753(12) 0.0702(12) 0.0637(11) -0.0330(9) -0.0195(9) 0.0231(9) C19 0.0526(9) 0.0640(10) 0.0495(9) -0.0209(8) -0.0102(7) 0.0175(8) C20 0.0607(10) 0.0495(9) 0.0477(9) -0.0060(7) -0.0043(7) 0.0174(8) C21 0.0790(13) 0.0700(12) 0.0449(9) -0.0032(8) 0.0000(9) 0.0216(10) C22 0.0837(14) 0.1178(18) 0.0444(10) -0.0202(11) -0.0151(9) 0.0336(13) C23 0.0700(12) 0.0978(15) 0.0612(11) -0.0399(11) -0.0223(9) 0.0175(10) C24 0.0499(9) 0.0672(11) 0.0534(9) -0.0209(8) -0.0152(7) 0.0107(8) O1' 0.0435(6) 0.0572(7) 0.0475(6) -0.0184(5) 0.0066(4) -0.0110(5) C2' 0.0380(8) 0.0511(9) 0.0426(8) -0.0132(7) -0.0029(6) -0.0084(6) C3' 0.0395(8) 0.0483(8) 0.0419(8) -0.0118(7) -0.0037(6) -0.0089(6) O4' 0.0384(5) 0.0459(6) 0.0416(5) -0.0170(4) 0.0011(4) -0.0074(4) C4a' 0.0357(7) 0.0392(7) 0.0356(7) -0.0106(6) -0.0042(6) 0.0023(6) C5' 0.0337(7) 0.0374(7) 0.0378(7) -0.0069(6) -0.0048(6) 0.0045(6) C6' 0.0388(7) 0.0379(7) 0.0416(8) -0.0097(6) -0.0106(6) 0.0048(6) C7' 0.0479(8) 0.0491(9) 0.0413(8) -0.0180(7) -0.0097(6) 0.0072(7) C8' 0.0428(8) 0.0546(9) 0.0368(8) -0.0127(7) 0.0008(6) 0.0022(7) C8a' 0.0355(7) 0.0423(8) 0.0407(8) -0.0091(6) -0.0034(6) -0.0001(6) O9' 0.0455(6) 0.0492(6) 0.0496(6) -0.0163(5) 0.0069(5) -0.0102(5) C10' 0.0486(9) 0.0387(8) 0.0500(9) -0.0125(7) -0.0138(7) 0.0047(7) O11' 0.0534(7) 0.0531(7) 0.0653(7) -0.0191(6) -0.0018(6) -0.0101(5) O12' 0.0738(8) 0.0575(7) 0.0647(7) -0.0287(6) -0.0040(6) -0.0150(6) C13' 0.0932(14) 0.0610(12) 0.0938(15) -0.0397(11) -0.0048(12) -0.0221(10) N14' 0.0451(7) 0.0471(7) 0.0433(7) -0.0048(6) -0.0058(5) -0.0108(6) C15' 0.0492(9) 0.0520(10) 0.0667(11) -0.0066(8) -0.0130(8) -0.0063(7) C16' 0.0714(12) 0.0579(12) 0.1034(16) -0.0021(11) -0.0333(11) -0.0001(10) O17' 0.1015(10) 0.0662(8) 0.0955(10) 0.0153(8) -0.0558(9) -0.0209(8) C18' 0.0980(15) 0.0698(13) 0.0781(13) 0.0173(10) -0.0406(12) -0.0342(11) C19' 0.0617(10) 0.0733(12) 0.0490(9) 0.0008(8) -0.0100(8) -0.0275(9) C20' 0.0603(10) 0.0544(10) 0.0459(9) -0.0185(7) 0.0006(7) -0.0165(8) C21' 0.0781(12) 0.0722(12) 0.0452(9) -0.0220(9) 0.0035(8) -0.0231(10) C22' 0.0865(14) 0.1051(16) 0.0421(10) -0.0068(10) -0.0118(9) -0.0270(12) C23' 0.0719(12) 0.0732(12) 0.0587(11) 0.0039(9) -0.0202(9) -0.0057(10) C24' 0.0492(9) 0.0634(10) 0.0534(9) -0.0095(8) -0.0131(7) -0.0029(8) _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 C8a 1.3646(17) . ? O1 C2 1.4764(18) . ? C2 N14 1.4203(19) . ? C2 C3 1.534(2) . ? C3 O4 1.4584(16) . ? C3 C20 1.517(2) . ? C3 C24 1.531(2) . ? O4 C4a 1.3697(17) . ? C4a C8a 1.386(2) . ? C4a C5 1.3925(19) . ? C5 O9 1.3516(17) . ? C5 C6 1.405(2) . ? C6 C7 1.401(2) . ? C6 C10 1.463(2) . ? C7 C8 1.372(2) . ? C8 C8a 1.391(2) . ? C10 O11 1.2174(18) . ? C10 O12 1.3331(19) . ? O12 C13 1.447(2) . ? N14 C19 1.4638(19) . ? N14 C15 1.4656(19) . ? C15 C16 1.505(2) . ? C16 O17 1.414(2) . ? O17 C18 1.418(2) . ? C18 C19 1.505(2) . ? C20 C21 1.523(2) . ? C21 C22 1.513(3) . ? C22 C23 1.511(3) . ? C23 C24 1.524(2) . ? O1' C8a' 1.3625(17) . ? O1' C2' 1.4753(17) . ? C2' N14' 1.421(2) . ? C2' C3' 1.531(2) . ? C3' O4' 1.4612(16) . ? C3' C20' 1.519(2) . ? C3' C24' 1.528(2) . ? O4' C4a' 1.3698(16) . ? C4a' C8a' 1.3840(19) . ? C4a' C5' 1.3951(19) . ? C5' O9' 1.3501(16) . ? C5' C6' 1.4054(19) . ? C6' C7' 1.399(2) . ? C6' C10' 1.462(2) . ? C7' C8' 1.369(2) . ? C8' C8a' 1.394(2) . ? C10' O11' 1.2174(18) . ? C10' O12' 1.3312(18) . ? O12' C13' 1.445(2) . ? N14' C19' 1.458(2) . ? N14' C15' 1.4650(19) . ? C15' C16' 1.501(3) . ? C16' O17' 1.413(2) . ? O17' C18' 1.415(2) . ? C18' C19' 1.501(3) . ? C20' C21' 1.526(2) . ? C21' C22' 1.510(3) . ? C22' C23' 1.512(3) . ? C23' C24' 1.524(2) . ? 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 C8a O1 C2 117.24(11) . . ? N14 C2 O1 112.68(11) . . ? N14 C2 C3 116.30(12) . . ? O1 C2 C3 109.86(11) . . ? O4 C3 C20 105.45(11) . . ? O4 C3 C24 108.58(12) . . ? C20 C3 C24 110.67(13) . . ? O4 C3 C2 109.69(11) . . ? C20 C3 C2 112.04(12) . . ? C24 C3 C2 110.26(12) . . ? C4a O4 C3 114.04(10) . . ? O4 C4a C8a 122.34(12) . . ? O4 C4a C5 117.73(12) . . ? C8a C4a C5 119.90(13) . . ? O9 C5 C4a 116.41(13) . . ? O9 C5 C6 123.75(13) . . ? C4a C5 C6 119.85(13) . . ? C7 C6 C5 118.92(13) . . ? C7 C6 C10 122.66(14) . . ? C5 C6 C10 118.41(13) . . ? C8 C7 C6 121.08(14) . . ? C7 C8 C8a 119.63(14) . . ? O1 C8a C4a 121.65(13) . . ? O1 C8a C8 117.71(13) . . ? C4a C8a C8 120.62(13) . . ? O11 C10 O12 121.96(14) . . ? O11 C10 C6 124.08(14) . . ? O12 C10 C6 113.96(14) . . ? C10 O12 C13 116.39(14) . . ? C2 N14 C19 113.50(12) . . ? C2 N14 C15 118.07(12) . . ? C19 N14 C15 108.41(12) . . ? N14 C15 C16 108.98(13) . . ? O17 C16 C15 112.63(15) . . ? C16 O17 C18 108.92(13) . . ? O17 C18 C19 111.50(14) . . ? N14 C19 C18 109.19(14) . . ? C3 C20 C21 112.31(14) . . ? C22 C21 C20 111.74(16) . . ? C23 C22 C21 111.23(15) . . ? C22 C23 C24 110.95(16) . . ? C23 C24 C3 111.55(14) . . ? C8a' O1' C2' 116.90(10) . . ? N14' C2' O1' 112.36(11) . . ? N14' C2' C3' 116.71(12) . . ? O1' C2' C3' 109.99(11) . . ? O4' C3' C20' 105.37(11) . . ? O4' C3' C24' 108.79(12) . . ? C20' C3' C24' 110.89(13) . . ? O4' C3' C2' 109.52(11) . . ? C20' C3' C2' 111.69(12) . . ? C24' C3' C2' 110.42(12) . . ? C4a' O4' C3' 113.73(10) . . ? O4' C4a' C8a' 122.25(12) . . ? O4' C4a' C5' 117.78(11) . . ? C8a' C4a' C5' 119.93(12) . . ? O9' C5' C4a' 116.43(12) . . ? O9' C5' C6' 123.86(12) . . ? C4a' C5' C6' 119.70(12) . . ? C7' C6' C5' 119.08(13) . . ? C7' C6' C10' 122.55(13) . . ? C5' C6' C10' 118.37(13) . . ? C8' C7' C6' 121.02(13) . . ? C7' C8' C8a' 119.75(13) . . ? O1' C8a' C4a' 122.00(12) . . ? O1' C8a' C8' 117.48(12) . . ? C4a' C8a' C8' 120.50(13) . . ? O11' C10' O12' 122.05(13) . . ? O11' C10' C6' 124.28(13) . . ? O12' C10' C6' 113.67(13) . . ? C10' O12' C13' 116.54(13) . . ? C2' N14' C19' 114.13(13) . . ? C2' N14' C15' 118.04(12) . . ? C19' N14' C15' 108.70(12) . . ? N14' C15' C16' 109.10(13) . . ? O17' C16' C15' 112.36(18) . . ? C16' O17' C18' 109.32(14) . . ? O17' C18' C19' 111.18(15) . . ? N14' C19' C18' 109.68(16) . . ? C3' C20' C21' 112.01(14) . . ? C22' C21' C20' 111.80(15) . . ? C21' C22' C23' 111.42(15) . . ? C22' C23' C24' 110.79(16) . . ? C23' C24' C3' 111.55(14) . . ? 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_publ_flag C8a O1 C2 C3 36.5(1) yes O1 C2 C3 O4 -55.5(1) yes C2 C3 O4 C4a 49.7(1) yes C3 O4 C4a C8a -24.1(1) yes O4 C4a C8a O1 3.0(1) yes C4a C8a O1 C2 -10.5(1) yes C8 C8a C4a C5 -0.6(1) yes C8a C4a C5 C6 -0.2(1) yes C4a C5 C6 C7 0.9(1) yes C5 C6 C7 C8 -0.6(1) yes C6 C7 C8 C8a -0.3(1) yes C7 C8 C8a C4a 0.9(1) yes O9 C5 C6 C10 1.5(1) yes C5 C6 C10 O11 3.4(1) yes C5 C6 C10 O12 -177.2(2) yes C6 C10 O12 C13 -179.6(2) yes O11 C10 O12 C13 -0.2(2) yes O1 C2 N14 C15 63.7(1) yes C19 N14 C15 C16 -57.9(2) yes N14 C15 C16 O17 58.8(2) yes C15 C16 O17 C18 -58.2(2) yes C16 O17 C18 C19 58.6(2) yes O17 C18 C19 N14 -60.4(2) yes C18 C19 N14 C15 59.1(2) yes C24 C3 C20 C21 -53.2(1) yes C3 C20 C21 C22 53.9(2) yes C20 C21 C22 C23 -55.0(2) yes C21 C22 C23 C24 56.3(2) yes C22 C23 C24 C3 -56.4(2) yes C23 C24 C3 C20 54.5(2) yes C8a' O1' C2' C3' -36.5(1) yes O1' C2' C3' O4' 56.0(1) yes C2' C3' O4' C4a' -50.1(1) yes C3' O4' C4a' C8a' 24.3(1) yes O4' C4a' C8a' O1' -2.8(1) yes C4a' C8a' O1' C2' 10.2(1) yes C8' C8a' C4a' C5' 0.7(1) yes C8a' C4a' C5' C6' 0.3(1) yes C4a' C5' C6' C7' -0.9(1) yes C5' C6' C7' C8' 0.7(1) yes C6' C7' C8' C8a' 0.3(1) yes C7' C8' C8a' C4a' -0.9(1) yes O9' C5' C6' C10' -1.5(1) yes C5' C6' C10' O11' -2.9(1) yes C5' C6' C10' O12' 177.7(2) yes C6' C10' O12' C13' -179.4(2) yes O11' C10' O12' C13' 1.2(2) yes O1' C2' N14' C15' -64.0(1) yes C19' N14' C15' C16' 57.3(2) yes N14' C15' C16' O17' -58.5(2) yes C15' C16' O17' C18' 58.6(2) yes C16' O17' C18' C19' -58.7(2) yes O17' C18' C19' N14' 59.9(2) yes C18' C19' N14' C15' -58.4(2) yes C24' C3' C20' C21' 53.2(1) yes C3' C20' C21' C22' -53.7(2) yes C20' C21' C22' C23' 55.1(2) yes C21' C22' C23' C24' -56.3(2) yes C22' C23' C24' C3' 56.4(2) yes C23' C24' C3' C20' -54.7(2) yes _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.174 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.031