# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Vittorio Caprio' _publ_contact_author_email V.CAPRIO@AUCKLAND.AC.NZ _publ_section_title ; A Concise Approach to the Core Structures of Pinnaic Acid and Halichlorine ; loop_ _publ_author_name 'Vittorio Caprio' 'G. R. Clark' 'Sung-Hyun Yang.' #===END data_ys556 _database_code_depnum_ccdc_archive 'CCDC 725418' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H28 N O3. Cl' _chemical_formula_sum 'C17 H28 Cl N O3' _chemical_formula_weight 329.85 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' Cl Cl 0.1484 0.1585 '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 _symmetry_space_group_name_Hall -p_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3424(1) _cell_length_b 9.2501(1) _cell_length_c 11.6434(2) _cell_angle_alpha 98.854(1) _cell_angle_beta 97.190(1) _cell_angle_gamma 94.937(1) _cell_volume 875.71(2) _cell_formula_units_Z 2 _cell_measurement_temperature 285(2) _cell_measurement_reflns_used 4466 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 27.98 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Sheldrick, 1997' _exptl_absorpt_correction_T_min 0.9383 _exptl_absorpt_correction_T_max 0.9641 _exptl_special_details ; ? ; _diffrn_ambient_temperature 285(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 APEX II' _diffrn_measurement_method 'Area detector \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% <2 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_reflns_number 20945 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.98 _reflns_number_total 4189 _reflns_number_gt 2934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT (Bruker, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0473P)^2^+0.2311P] 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 4189 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.4341(2) 0.64479(15) 0.66257(15) 0.0716(5) Uani 1 1 d . . . HO1 H 0.387(4) 0.673(3) 0.598(3) 0.107(10) Uiso 1 1 d . . . O2 O 0.71775(19) 0.44145(16) 1.03189(12) 0.0722(5) Uani 1 1 d . . . O3 O 0.88952(17) 0.26980(15) 1.03734(12) 0.0637(4) Uani 1 1 d . . . N N 0.44207(16) 0.19862(13) 0.72486(11) 0.0360(3) Uani 1 1 d . . . HN H 0.5156 0.2235 0.6778 0.043 Uiso 1 1 calc R . . C1 C 0.27974(19) 0.24641(17) 0.67507(13) 0.0377(3) Uani 1 1 d . . . C2 C 0.28479(19) 0.41475(17) 0.68105(14) 0.0401(4) Uani 1 1 d . . . H2 H 0.2698 0.4617 0.7598 0.048 Uiso 1 1 calc R . . C3 C 0.1358(2) 0.4263(2) 0.59223(15) 0.0505(4) Uani 1 1 d . . . H3A H 0.0369 0.4186 0.6278 0.061 Uiso 1 1 calc R . . H3B H 0.1457 0.5191 0.5633 0.061 Uiso 1 1 calc R . . C4 C 0.1346(3) 0.2971(2) 0.49298(16) 0.0611(5) Uani 1 1 d . . . H4A H 0.1778 0.3307 0.4270 0.073 Uiso 1 1 calc R . . H4B H 0.0245 0.2510 0.4665 0.073 Uiso 1 1 calc R . . C5 C 0.2411(2) 0.1869(2) 0.54230(14) 0.0466(4) Uani 1 1 d . . . H5A H 0.3401 0.1832 0.5067 0.056 Uiso 1 1 calc R . . H5B H 0.1830 0.0890 0.5281 0.056 Uiso 1 1 calc R . . C6 C 0.4345(2) 0.48959(18) 0.64362(17) 0.0500(4) Uani 1 1 d . . . H6A H 0.5313 0.4639 0.6879 0.060 Uiso 1 1 calc R . . H6B H 0.4372 0.4546 0.5610 0.060 Uiso 1 1 calc R . . C7 C 0.7547(2) 0.3219(2) 0.99533(15) 0.0482(4) Uani 1 1 d . . . C8 C 0.9938(3) 0.3634(3) 1.13471(19) 0.0707(6) Uani 1 1 d . . . H8A H 0.9466 0.3627 1.2067 0.085 Uiso 1 1 calc R . . H8B H 1.0060 0.4639 1.1199 0.085 Uiso 1 1 calc R . . C9 C 1.1530(3) 0.3052(3) 1.1456(2) 0.0831(7) Uani 1 1 d . . . H9A H 1.1392 0.2053 1.1589 0.125 Uiso 1 1 calc R . . H9B H 1.2240 0.3639 1.2104 0.125 Uiso 1 1 calc R . . H9C H 1.1996 0.3084 1.0746 0.125 Uiso 1 1 calc R . . C1' C 0.3091(3) -0.0185(2) 0.7908(2) 0.0638(5) Uani 1 1 d . . . H1'1 H 0.3421 0.0251 0.8725 0.077 Uiso 1 1 calc R . . H1'2 H 0.3028 -0.1246 0.7851 0.077 Uiso 1 1 calc R . . C2' C 0.1421(3) 0.0256(2) 0.7485(2) 0.0721(6) Uani 1 1 d . . . H2'1 H 0.0668 0.0011 0.8014 0.087 Uiso 1 1 calc R . . H2'2 H 0.1021 -0.0301 0.6712 0.087 Uiso 1 1 calc R . . C3' C 0.1480(2) 0.1901(2) 0.74299(18) 0.0541(5) Uani 1 1 d . . . H3'1 H 0.1666 0.2446 0.8224 0.065 Uiso 1 1 calc R . . H3'2 H 0.0431 0.2101 0.7064 0.065 Uiso 1 1 calc R . . C6' C 0.5055(2) 0.27837(19) 0.84633(14) 0.0451(4) Uani 1 1 d . . . H6'1 H 0.5295 0.3823 0.8440 0.054 Uiso 1 1 calc R . . H6'2 H 0.4225 0.2682 0.8968 0.054 Uiso 1 1 calc R . . C7' C 0.6558(2) 0.21970(18) 0.89656(14) 0.0431(4) Uani 1 1 d . . . C8' C 0.6979(2) 0.08924(19) 0.85484(15) 0.0480(4) Uani 1 1 d . . . H8' H 0.7914 0.0585 0.8916 0.058 Uiso 1 1 calc R . . C9' C 0.6028(2) -0.01069(18) 0.75183(16) 0.0505(4) Uani 1 1 d . . . H9'1 H 0.5932 -0.1100 0.7694 0.061 Uiso 1 1 calc R . . H9'2 H 0.6621 -0.0111 0.6853 0.061 Uiso 1 1 calc R . . C9A' C 0.4338(2) 0.03217(17) 0.71797(15) 0.0446(4) Uani 1 1 d . . . H9A' H 0.3970 -0.0129 0.6360 0.054 Uiso 1 1 calc R . . Cl Cl 0.29078(6) 0.76714(5) 0.43580(4) 0.05719(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0911(12) 0.0365(7) 0.0785(10) 0.0067(7) -0.0145(9) 0.0020(7) O2 0.0830(10) 0.0638(9) 0.0569(8) -0.0179(7) -0.0211(7) 0.0302(8) O3 0.0578(8) 0.0610(8) 0.0608(8) -0.0082(6) -0.0209(7) 0.0179(7) N 0.0370(7) 0.0339(7) 0.0340(7) -0.0001(5) -0.0001(5) 0.0047(5) C1 0.0345(8) 0.0402(8) 0.0354(8) 0.0008(6) -0.0012(6) 0.0051(7) C2 0.0411(9) 0.0405(9) 0.0351(8) -0.0012(6) -0.0027(7) 0.0108(7) C3 0.0461(10) 0.0548(11) 0.0476(10) 0.0040(8) -0.0059(8) 0.0143(8) C4 0.0631(12) 0.0695(13) 0.0433(10) -0.0035(9) -0.0130(9) 0.0177(10) C5 0.0453(10) 0.0468(10) 0.0407(9) -0.0058(7) -0.0050(7) 0.0049(8) C6 0.0531(11) 0.0361(9) 0.0586(11) 0.0078(8) -0.0007(9) 0.0055(8) C7 0.0516(10) 0.0514(10) 0.0390(9) 0.0034(7) -0.0035(8) 0.0135(8) C8 0.0647(13) 0.0731(14) 0.0611(13) -0.0076(11) -0.0226(11) 0.0123(11) C9 0.0611(14) 0.0923(18) 0.0889(17) 0.0146(14) -0.0158(13) 0.0075(13) C1' 0.0709(14) 0.0473(11) 0.0776(14) 0.0217(10) 0.0156(11) 0.0034(10) C2' 0.0558(13) 0.0651(14) 0.0998(18) 0.0261(12) 0.0194(12) -0.0044(10) C3' 0.0429(10) 0.0610(12) 0.0600(11) 0.0125(9) 0.0097(9) 0.0067(9) C6' 0.0537(10) 0.0411(9) 0.0355(8) -0.0036(7) -0.0058(7) 0.0130(8) C7' 0.0480(10) 0.0423(9) 0.0364(8) 0.0027(7) -0.0031(7) 0.0103(7) C8' 0.0501(10) 0.0450(10) 0.0471(10) 0.0059(7) -0.0032(8) 0.0132(8) C9' 0.0592(11) 0.0358(9) 0.0533(10) 0.0002(7) -0.0007(9) 0.0132(8) C9A' 0.0515(10) 0.0321(8) 0.0467(9) 0.0005(7) 0.0003(8) 0.0045(7) Cl 0.0482(3) 0.0599(3) 0.0688(3) 0.0177(2) 0.0156(2) 0.0122(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 O1 C6 1.419(2) . ? O1 HO1 0.89(3) . ? O2 C7 1.202(2) . ? O3 C7 1.328(2) . ? O3 C8 1.454(2) . ? N C6' 1.4996(19) . ? N C9A' 1.5245(19) . ? N C1 1.5333(19) . ? N HN 0.9100 . ? C1 C3' 1.533(2) . ? C1 C5 1.542(2) . ? C1 C2 1.545(2) . ? C2 C6 1.519(2) . ? C2 C3 1.537(2) . ? C2 H2 0.9800 . ? C3 C4 1.528(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.538(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C7' 1.480(2) . ? C8 C9 1.474(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C1' C9A' 1.510(3) . ? C1' C2' 1.529(3) . ? C1' H1'1 0.9700 . ? C1' H1'2 0.9700 . ? C2' C3' 1.530(3) . ? C2' H2'1 0.9700 . ? C2' H2'2 0.9700 . ? C3' H3'1 0.9700 . ? C3' H3'2 0.9700 . ? C6' C7' 1.496(2) . ? C6' H6'1 0.9700 . ? C6' H6'2 0.9700 . ? C7' C8' 1.323(2) . ? C8' C9' 1.489(2) . ? C8' H8' 0.9300 . ? C9' C9A' 1.519(2) . ? C9' H9'1 0.9700 . ? C9' H9'2 0.9700 . ? C9A' H9A' 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 HO1 109.7(19) . . ? C7 O3 C8 116.90(15) . . ? C6' N C9A' 111.81(12) . . ? C6' N C1 112.96(11) . . ? C9A' N C1 111.80(12) . . ? C6' N HN 106.6 . . ? C9A' N HN 106.6 . . ? C1 N HN 106.6 . . ? N C1 C3' 108.20(13) . . ? N C1 C5 109.98(12) . . ? C3' C1 C5 112.01(14) . . ? N C1 C2 112.85(12) . . ? C3' C1 C2 110.57(13) . . ? C5 C1 C2 103.23(12) . . ? C6 C2 C3 108.84(14) . . ? C6 C2 C1 115.73(13) . . ? C3 C2 C1 101.44(13) . . ? C6 C2 H2 110.2 . . ? C3 C2 H2 110.2 . . ? C1 C2 H2 110.2 . . ? C4 C3 C2 104.81(13) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? C3 C4 C5 107.05(14) . . ? C3 C4 H4A 110.3 . . ? C5 C4 H4A 110.3 . . ? C3 C4 H4B 110.3 . . ? C5 C4 H4B 110.3 . . ? H4A C4 H4B 108.6 . . ? C4 C5 C1 104.61(13) . . ? C4 C5 H5A 110.8 . . ? C1 C5 H5A 110.8 . . ? C4 C5 H5B 110.8 . . ? C1 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? O1 C6 C2 111.15(15) . . ? O1 C6 H6A 109.4 . . ? C2 C6 H6A 109.4 . . ? O1 C6 H6B 109.4 . . ? C2 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? O2 C7 O3 123.60(16) . . ? O2 C7 C7' 123.03(16) . . ? O3 C7 C7' 113.36(14) . . ? O3 C8 C9 107.62(18) . . ? O3 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? O3 C8 H8B 110.2 . . ? C9 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C9A' C1' C2' 110.70(17) . . ? C9A' C1' H1'1 109.5 . . ? C2' C1' H1'1 109.5 . . ? C9A' C1' H1'2 109.5 . . ? C2' C1' H1'2 109.5 . . ? H1'1 C1' H1'2 108.1 . . ? C1' C2' C3' 112.00(17) . . ? C1' C2' H2'1 109.2 . . ? C3' C2' H2'1 109.2 . . ? C1' C2' H2'2 109.2 . . ? C3' C2' H2'2 109.2 . . ? H2'1 C2' H2'2 107.9 . . ? C2' C3' C1 114.05(16) . . ? C2' C3' H3'1 108.7 . . ? C1 C3' H3'1 108.7 . . ? C2' C3' H3'2 108.7 . . ? C1 C3' H3'2 108.7 . . ? H3'1 C3' H3'2 107.6 . . ? C7' C6' N 111.61(13) . . ? C7' C6' H6'1 109.3 . . ? N C6' H6'1 109.3 . . ? C7' C6' H6'2 109.3 . . ? N C6' H6'2 109.3 . . ? H6'1 C6' H6'2 108.0 . . ? C8' C7' C7 123.07(15) . . ? C8' C7' C6' 122.93(15) . . ? C7 C7' C6' 114.00(14) . . ? C7' C8' C9' 123.17(16) . . ? C7' C8' H8' 118.4 . . ? C9' C8' H8' 118.4 . . ? C8' C9' C9A' 113.62(14) . . ? C8' C9' H9'1 108.8 . . ? C9A' C9' H9'1 108.8 . . ? C8' C9' H9'2 108.8 . . ? C9A' C9' H9'2 108.8 . . ? H9'1 C9' H9'2 107.7 . . ? C1' C9A' C9' 114.30(15) . . ? C1' C9A' N 109.72(14) . . ? C9' C9A' N 109.47(13) . . ? C1' C9A' H9A' 107.7 . . ? C9' C9A' H9A' 107.7 . . ? N C9A' H9A' 107.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 HO1 Cl 0.89(3) 2.29(3) 3.1691(17) 173(3) . N HN Cl 0.91 2.22 3.1099(14) 167.0 2_666 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.445 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.037 #===END # Attachment 'Combined.cif' data_ysh01 _database_code_depnum_ccdc_archive 'CCDC 725419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H17 N O2' _chemical_formula_sum 'C10 H17 N O2' _chemical_formula_weight 183.25 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 P21/n _symmetry_space_group_name_Hall -p_2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5510(2) _cell_length_b 10.7255(2) _cell_length_c 10.3379(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.330(2) _cell_angle_gamma 90.00 _cell_volume 942.35(3) _cell_formula_units_Z 4 _cell_measurement_temperature 84(2) _cell_measurement_reflns_used 5151 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.10 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_min 0.9567 _exptl_absorpt_correction_T_max 0.9652 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Sheldrick, 1997' _diffrn_ambient_temperature 84(1) _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 SMART CCD' _diffrn_measurement_method 'Area detector \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% <2 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _reflns_threshold_expression I>2\s(I) _diffrn_reflns_number 5788 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.10 _reflns_number_total 2069 _reflns_number_gt 1805 _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT (Bruker, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0847P)^2^+0.6273P] 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 2069 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1626 _refine_ls_wR_factor_gt 0.1569 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 -0.10265(15) 0.37623(13) 0.15470(12) 0.0275(3) Uani 1 1 d . . . O2 O 0.04952(16) 0.54124(11) 0.35938(12) 0.0242(3) Uani 1 1 d . . . HO2 H 0.035(3) 0.572(3) 0.433(3) 0.050(8) Uiso 1 1 d . . . N N -0.00032(16) 0.41359(12) 0.38114(13) 0.0182(3) Uani 1 1 d . . . C1 C 0.16951(19) 0.31705(16) 0.22132(16) 0.0197(4) Uani 1 1 d . . . H1 H 0.1576 0.2307 0.1908 0.024 Uiso 1 1 calc R . . C2 C 0.3437(2) 0.35494(19) 0.22423(19) 0.0282(4) Uani 1 1 d . . . H2A H 0.4101 0.2817 0.2233 0.034 Uiso 1 1 calc R . . H2B H 0.3593 0.4063 0.1495 0.034 Uiso 1 1 calc R . . C3 C 0.3826(2) 0.4275(2) 0.3490(2) 0.0324(5) Uiso 1 1 d . . . H3A H 0.3541 0.5146 0.3369 0.039 Uiso 1 1 calc R . . H3B H 0.4939 0.4218 0.3791 0.039 Uiso 1 1 calc R . . C4 C 0.28325(19) 0.36471(16) 0.44570(17) 0.0213(4) Uani 1 1 d . . . H4A H 0.2611 0.4229 0.5132 0.026 Uiso 1 1 calc R . . H4B H 0.3382 0.2933 0.4863 0.026 Uiso 1 1 calc R . . C5 C 0.12963(18) 0.32350(15) 0.36512(15) 0.0167(4) Uani 1 1 d . . . C6 C 0.0582(2) 0.39965(17) 0.13357(17) 0.0247(4) Uani 1 1 d . . . H6B H 0.0833 0.4866 0.1515 0.030 Uiso 1 1 calc R . . H6C H 0.0719 0.3833 0.0432 0.030 Uiso 1 1 calc R . . C7 C -0.13635(19) 0.38662(17) 0.28774(17) 0.0234(4) Uani 1 1 d . . . H7 H -0.2141 0.4531 0.2929 0.028 Uiso 1 1 calc R . . C8 C -0.20720(19) 0.26430(18) 0.32960(18) 0.0268(4) Uani 1 1 d . . . H8A H -0.2965 0.2422 0.2678 0.032 Uiso 1 1 calc R . . H8B H -0.2447 0.2753 0.4141 0.032 Uiso 1 1 calc R . . C9 C -0.0865(2) 0.15873(17) 0.33730(18) 0.0237(4) Uani 1 1 d . . . H9A H -0.0678 0.1342 0.2500 0.028 Uiso 1 1 calc R . . H9B H -0.1279 0.0871 0.3795 0.028 Uiso 1 1 calc R . . C10 C 0.06932(18) 0.19911(15) 0.41350(16) 0.0189(4) Uani 1 1 d . . . H10A H 0.1479 0.1351 0.4056 0.023 Uiso 1 1 calc R . . H10B H 0.0548 0.2068 0.5049 0.023 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 0.0240(6) 0.0381(8) 0.0186(6) -0.0051(5) -0.0064(5) 0.0060(5) O2 0.0364(7) 0.0159(6) 0.0202(6) -0.0007(5) 0.0032(5) 0.0001(5) N 0.0191(7) 0.0159(7) 0.0187(7) -0.0017(5) -0.0020(5) 0.0014(5) C1 0.0198(8) 0.0213(8) 0.0178(8) -0.0007(6) 0.0014(6) 0.0008(6) C2 0.0219(9) 0.0329(10) 0.0306(10) 0.0032(7) 0.0069(7) -0.0016(7) C4 0.0177(8) 0.0228(8) 0.0220(8) 0.0014(6) -0.0049(6) -0.0022(6) C5 0.0157(7) 0.0179(8) 0.0159(7) -0.0002(6) -0.0013(6) 0.0006(6) C6 0.0297(9) 0.0279(9) 0.0156(8) 0.0001(6) -0.0008(6) 0.0040(7) C7 0.0179(8) 0.0298(9) 0.0210(8) -0.0051(7) -0.0039(6) 0.0072(7) C8 0.0141(7) 0.0354(10) 0.0299(9) -0.0086(7) -0.0012(6) -0.0014(7) C9 0.0194(8) 0.0227(8) 0.0286(9) -0.0048(7) 0.0015(6) -0.0052(6) C10 0.0168(7) 0.0182(8) 0.0213(8) 0.0007(6) 0.0005(6) -0.0001(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.438(2) . ? O1 C7 1.440(2) . ? O2 N 1.4587(18) . ? O2 HO2 0.85(3) . ? N C7 1.456(2) . ? N C5 1.495(2) . ? C1 C6 1.524(2) . ? C1 C2 1.541(2) . ? C1 C5 1.563(2) . ? C1 H1 0.9800 . ? C2 C3 1.512(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.537(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.541(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C10 1.534(2) . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C7 C8 1.528(3) . ? C7 H7 0.9800 . ? C8 C9 1.529(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.533(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? 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 C7 115.27(13) . . ? N O2 HO2 99(2) . . ? C7 N O2 108.04(12) . . ? C7 N C5 110.32(12) . . ? O2 N C5 110.86(12) . . ? C6 C1 C2 113.41(15) . . ? C6 C1 C5 110.66(13) . . ? C2 C1 C5 106.35(13) . . ? C6 C1 H1 108.8 . . ? C2 C1 H1 108.8 . . ? C5 C1 H1 108.8 . . ? C3 C2 C1 105.87(15) . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2B 110.6 . . ? C1 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? C2 C3 C4 104.15(16) . . ? C2 C3 H3A 110.9 . . ? C4 C3 H3A 110.9 . . ? C2 C3 H3B 110.9 . . ? C4 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? C3 C4 C5 105.87(14) . . ? C3 C4 H4A 110.6 . . ? C5 C4 H4A 110.6 . . ? C3 C4 H4B 110.6 . . ? C5 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? N C5 C10 104.19(12) . . ? N C5 C4 110.75(13) . . ? C10 C5 C4 111.75(13) . . ? N C5 C1 112.12(12) . . ? C10 C5 C1 112.84(13) . . ? C4 C5 C1 105.34(13) . . ? O1 C6 C1 110.67(14) . . ? O1 C6 H6B 109.5 . . ? C1 C6 H6B 109.5 . . ? O1 C6 H6C 109.5 . . ? C1 C6 H6C 109.5 . . ? H6B C6 H6C 108.1 . . ? O1 C7 N 114.78(14) . . ? O1 C7 C8 109.35(14) . . ? N C7 C8 107.18(14) . . ? O1 C7 H7 108.5 . . ? N C7 H7 108.5 . . ? C8 C7 H7 108.5 . . ? C7 C8 C9 111.36(14) . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C10 111.17(14) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C5 112.48(13) . . ? C9 C10 H10A 109.1 . . ? C5 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C5 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 HO2 N 0.85(3) 1.98(3) 2.8030(19) 162(3) 3_566 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.151 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.060 #===END data_ysh2 _database_code_depnum_ccdc_archive 'CCDC 725420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H25 N O2' _chemical_formula_sum 'C18 H25 N O2' _chemical_formula_weight 287.39 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 p_21 _symmetry_space_group_name_Hall p_2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.0336(1) _cell_length_b 20.6330(3) _cell_length_c 10.9160(1) _cell_angle_alpha 90.00 _cell_angle_beta 102.955(1) _cell_angle_gamma 90.00 _cell_volume 1543.85(3) _cell_formula_units_Z 4 _cell_measurement_temperature 84(2) _cell_measurement_reflns_used 6646 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 26.42 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Sheldrick, 1997' _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_T_max 0.9765 _exptl_special_details ; ? ; _diffrn_ambient_temperature 84(1) _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 SMART CCD' _diffrn_measurement_method 'Area detector \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% <2 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _reflns_threshold_expression I>2\s(I) _diffrn_reflns_number 7756 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.42 _reflns_number_total 4206 _reflns_number_gt 3972 _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT (Bruker, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0577P)^2^+0.3553P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(8) _refine_ls_number_reflns 4206 _refine_ls_number_parameters 387 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0872 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _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 O1A O 0.20275(18) 0.69442(7) 0.45762(11) 0.0163(3) Uani 1 1 d . . . O2A O -0.0832(2) 0.89681(7) 0.13006(13) 0.0236(3) Uani 1 1 d . . . HO2A H -0.202(4) 0.8964(13) 0.122(2) 0.020(6) Uiso 1 1 d . . . NA N 0.0688(2) 0.74193(8) 0.38048(14) 0.0141(3) Uani 1 1 d . . . C1A C 0.0569(3) 0.72420(10) 0.24761(16) 0.0151(4) Uani 1 1 d . . . C2A C -0.0480(3) 0.77913(10) 0.16107(17) 0.0168(4) Uani 1 1 d . . . H2A H -0.1893 0.7718 0.1422 0.020 Uiso 1 1 calc R . . C3A C 0.0293(3) 0.77101(11) 0.03966(17) 0.0219(4) Uani 1 1 d . . . H3A1 H -0.0572 0.7434 -0.0200 0.026 Uiso 1 1 calc R . . H3A2 H 0.0383 0.8128 0.0006 0.026 Uiso 1 1 calc R . . C4A C 0.2332(3) 0.73975(11) 0.08025(18) 0.0245(4) Uani 1 1 d . . . H4A1 H 0.2397 0.7003 0.0330 0.029 Uiso 1 1 calc R . . H4A2 H 0.3329 0.7694 0.0658 0.029 Uiso 1 1 calc R . . C5A C 0.2632(3) 0.72453(11) 0.22150(17) 0.0183(4) Uani 1 1 d . . . H5A1 H 0.3255 0.6827 0.2409 0.022 Uiso 1 1 calc R . . H5A2 H 0.3437 0.7574 0.2716 0.022 Uiso 1 1 calc R . . C6A C -0.0022(3) 0.84678(10) 0.21707(18) 0.0187(4) Uani 1 1 d . . . H6A1 H -0.0542 0.8508 0.2919 0.022 Uiso 1 1 calc R . . H6A2 H 0.1381 0.8523 0.2418 0.022 Uiso 1 1 calc R . . C7A C 0.3421(3) 0.75487(10) 0.64988(16) 0.0154(4) Uani 1 1 d . . . C8A C 0.3725(3) 0.76259(10) 0.77979(17) 0.0187(4) Uani 1 1 d . . . H8A H 0.2944 0.7401 0.8237 0.022 Uiso 1 1 calc R . . C9A C 0.5180(3) 0.80344(10) 0.84454(18) 0.0203(4) Uani 1 1 d . . . H9A H 0.5379 0.8076 0.9313 0.024 Uiso 1 1 calc R . . C10A C 0.6336(3) 0.83812(10) 0.77992(18) 0.0211(4) Uani 1 1 d . . . H10A H 0.7315 0.8653 0.8232 0.025 Uiso 1 1 calc R . . C11A C 0.6019(3) 0.83193(10) 0.64969(19) 0.0207(4) Uani 1 1 d . . . H11A H 0.6770 0.8557 0.6056 0.025 Uiso 1 1 calc R . . C12A C 0.4577(3) 0.79010(10) 0.58536(17) 0.0185(4) Uani 1 1 d . . . H12A H 0.4386 0.7857 0.4987 0.022 Uiso 1 1 calc R . . C3AA C -0.1107(3) 0.73096(10) 0.42819(17) 0.0164(4) Uani 1 1 d . . . H3AA H -0.2035 0.7663 0.4008 0.020 Uiso 1 1 calc R . . C2'A C 0.1848(3) 0.70866(10) 0.58308(17) 0.0165(4) Uani 1 1 d . . . H2'A H 0.1956 0.6681 0.6308 0.020 Uiso 1 1 calc R . . C3'A C -0.0246(3) 0.73626(10) 0.57012(16) 0.0181(4) Uani 1 1 d . . . H3'1 H -0.0986 0.7106 0.6176 0.022 Uiso 1 1 calc R . . H3'2 H -0.0211 0.7809 0.5982 0.022 Uiso 1 1 calc R . . C4'A C -0.2110(3) 0.66542(11) 0.39036(18) 0.0206(4) Uani 1 1 d . . . H4'1 H -0.1328 0.6310 0.4370 0.025 Uiso 1 1 calc R . . H4'2 H -0.3373 0.6651 0.4122 0.025 Uiso 1 1 calc R . . C5'A C -0.2382(3) 0.65272(11) 0.24996(18) 0.0214(4) Uani 1 1 d . . . H5'1 H -0.3292 0.6839 0.2029 0.026 Uiso 1 1 calc R . . H5'2 H -0.2918 0.6097 0.2301 0.026 Uiso 1 1 calc R . . C6'A C -0.0418(3) 0.65824(10) 0.21258(18) 0.0193(4) Uani 1 1 d . . . H6'1 H -0.0615 0.6518 0.1226 0.023 Uiso 1 1 calc R . . H6'2 H 0.0441 0.6242 0.2540 0.023 Uiso 1 1 calc R . . O1B O 0.64919(18) 0.05566(7) 0.34534(11) 0.0158(3) Uani 1 1 d . . . O2B O 0.5207(2) -0.10148(7) 0.14149(14) 0.0213(3) Uani 1 1 d . . . HO2B H 0.547(3) -0.0762(13) 0.201(2) 0.017(6) Uiso 1 1 d . . . NB N 0.5100(2) 0.01475(8) 0.25567(14) 0.0143(3) Uani 1 1 d . . . C1B C 0.4957(3) 0.04585(9) 0.13060(16) 0.0143(4) Uani 1 1 d . . . C2B C 0.4000(3) -0.00227(10) 0.02116(17) 0.0164(4) Uani 1 1 d . . . H2B H 0.2769 0.0170 -0.0241 0.020 Uiso 1 1 calc R . . C3B C 0.5413(3) -0.00338(10) -0.06935(17) 0.0192(4) Uani 1 1 d . . . H3B1 H 0.6145 -0.0436 -0.0603 0.023 Uiso 1 1 calc R . . H3B2 H 0.4692 0.0006 -0.1559 0.023 Uiso 1 1 calc R . . C4B C 0.6779(3) 0.05410(11) -0.03303(17) 0.0187(4) Uani 1 1 d . . . H4B1 H 0.6197 0.0938 -0.0722 0.022 Uiso 1 1 calc R . . H4B2 H 0.8015 0.0469 -0.0562 0.022 Uiso 1 1 calc R . . C5B C 0.7033(3) 0.05644(10) 0.10974(16) 0.0157(4) Uani 1 1 d . . . H5B1 H 0.7547 0.0981 0.1429 0.019 Uiso 1 1 calc R . . H5B2 H 0.7908 0.0225 0.1500 0.019 Uiso 1 1 calc R . . C6B C 0.3560(3) -0.07098(10) 0.05886(19) 0.0195(4) Uani 1 1 d . . . H6B1 H 0.2478 -0.0696 0.1004 0.023 Uiso 1 1 calc R . . H6B2 H 0.3162 -0.0971 -0.0164 0.023 Uiso 1 1 calc R . . C7B C 0.7948(3) -0.00255(10) 0.53928(17) 0.0163(4) Uani 1 1 d . . . C8B C 0.9074(3) -0.04071(10) 0.47705(18) 0.0190(4) Uani 1 1 d . . . H8B H 0.8829 -0.0401 0.3897 0.023 Uiso 1 1 calc R . . C9B C 1.0558(3) -0.07956(11) 0.54473(19) 0.0221(4) Uani 1 1 d . . . H9B H 1.1291 -0.1052 0.5024 0.026 Uiso 1 1 calc R . . C10B C 1.0955(3) -0.08036(11) 0.67548(19) 0.0234(4) Uani 1 1 d . . . H10B H 1.1961 -0.1059 0.7206 0.028 Uiso 1 1 calc R . . C11B C 0.9831(3) -0.04257(11) 0.73824(18) 0.0220(4) Uani 1 1 d . . . H11B H 1.0082 -0.0431 0.8256 0.026 Uiso 1 1 calc R . . C12B C 0.8336(3) -0.00414(10) 0.67044(17) 0.0190(4) Uani 1 1 d . . . H12B H 0.7586 0.0207 0.7128 0.023 Uiso 1 1 calc R . . C3AB C 0.3337(3) 0.01747(10) 0.31057(17) 0.0165(4) Uani 1 1 d . . . H3AB H 0.2434 -0.0174 0.2750 0.020 Uiso 1 1 calc R . . C2'B C 0.6254(3) 0.03819(10) 0.46917(16) 0.0163(4) Uani 1 1 d . . . H2'B H 0.6177 0.0779 0.5172 0.020 Uiso 1 1 calc R . . C3'B C 0.4277(3) 0.00224(11) 0.44819(17) 0.0190(4) Uani 1 1 d . . . H3'3 H 0.4465 -0.0440 0.4613 0.023 Uiso 1 1 calc R . . H3'4 H 0.3489 0.0186 0.5039 0.023 Uiso 1 1 calc R . . C4'B C 0.2262(3) 0.08238(10) 0.29410(18) 0.0190(4) Uani 1 1 d . . . H4'3 H 0.3037 0.1147 0.3478 0.023 Uiso 1 1 calc R . . H4'4 H 0.1029 0.0780 0.3191 0.023 Uiso 1 1 calc R . . C5'B C 0.1889(3) 0.10468(10) 0.15723(17) 0.0191(4) Uani 1 1 d . . . H5'3 H 0.1226 0.1462 0.1480 0.023 Uiso 1 1 calc R . . H5'4 H 0.1066 0.0735 0.1034 0.023 Uiso 1 1 calc R . . C6'B C 0.3849(3) 0.11075(10) 0.11910(17) 0.0166(4) Uani 1 1 d . . . H6'3 H 0.4647 0.1428 0.1722 0.020 Uiso 1 1 calc R . . H6'4 H 0.3624 0.1259 0.0329 0.020 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 O1A 0.0165(6) 0.0169(7) 0.0143(6) 0.0011(5) 0.0011(5) 0.0042(5) O2A 0.0207(7) 0.0201(8) 0.0309(8) 0.0083(6) 0.0076(6) 0.0044(6) NA 0.0130(7) 0.0153(8) 0.0139(7) 0.0017(6) 0.0028(5) 0.0029(6) C1A 0.0151(8) 0.0160(9) 0.0138(8) -0.0001(7) 0.0020(7) -0.0003(7) C2A 0.0153(8) 0.0180(9) 0.0166(8) 0.0025(8) 0.0026(6) 0.0019(7) C3A 0.0263(10) 0.0221(11) 0.0170(9) 0.0008(8) 0.0045(7) 0.0005(9) C4A 0.0264(10) 0.0298(12) 0.0202(9) 0.0038(9) 0.0113(7) 0.0064(9) C5A 0.0158(9) 0.0221(10) 0.0172(9) -0.0015(8) 0.0044(7) 0.0022(8) C6A 0.0189(9) 0.0173(10) 0.0203(9) 0.0033(8) 0.0054(7) 0.0013(8) C7A 0.0143(8) 0.0140(9) 0.0173(8) 0.0018(8) 0.0020(6) 0.0045(7) C8A 0.0204(9) 0.0181(10) 0.0175(9) 0.0026(8) 0.0043(7) 0.0039(8) C9A 0.0211(9) 0.0225(11) 0.0162(9) -0.0023(8) 0.0018(7) 0.0033(8) C10A 0.0159(9) 0.0200(10) 0.0252(10) -0.0052(8) 0.0002(7) 0.0014(8) C11A 0.0169(9) 0.0201(10) 0.0262(10) -0.0007(8) 0.0069(7) -0.0002(8) C12A 0.0194(9) 0.0207(10) 0.0155(8) 0.0005(8) 0.0039(7) 0.0019(8) C3AA 0.0135(8) 0.0188(10) 0.0179(9) 0.0012(8) 0.0059(6) -0.0004(7) C2'A 0.0200(9) 0.0158(10) 0.0139(8) 0.0009(7) 0.0043(7) 0.0004(8) C3'A 0.0175(9) 0.0206(10) 0.0170(9) -0.0008(8) 0.0058(7) -0.0016(7) C4'A 0.0185(9) 0.0241(11) 0.0187(9) 0.0017(8) 0.0033(7) -0.0061(8) C5'A 0.0202(9) 0.0206(10) 0.0223(10) -0.0009(8) 0.0024(7) -0.0064(8) C6'A 0.0217(9) 0.0177(10) 0.0174(9) -0.0008(8) 0.0024(7) -0.0001(8) O1B 0.0169(6) 0.0171(7) 0.0124(6) -0.0006(5) 0.0017(5) -0.0043(5) O2B 0.0230(7) 0.0163(7) 0.0239(7) -0.0018(6) 0.0041(5) -0.0002(6) NB 0.0115(7) 0.0157(8) 0.0150(7) -0.0017(6) 0.0015(5) -0.0026(6) C1B 0.0142(8) 0.0129(9) 0.0154(8) 0.0009(7) 0.0026(6) -0.0008(7) C2B 0.0135(7) 0.0187(10) 0.0157(8) -0.0019(8) 0.0006(6) 0.0002(7) C3B 0.0216(9) 0.0212(10) 0.0158(8) -0.0025(8) 0.0061(7) -0.0018(8) C4B 0.0164(8) 0.0230(10) 0.0172(9) 0.0017(8) 0.0046(7) -0.0015(8) C5B 0.0135(8) 0.0173(9) 0.0161(8) -0.0002(7) 0.0028(6) -0.0015(7) C6B 0.0160(8) 0.0191(10) 0.0231(9) -0.0042(8) 0.0040(7) -0.0042(8) C7B 0.0158(8) 0.0155(9) 0.0167(9) 0.0012(8) 0.0017(6) -0.0033(7) C8B 0.0176(8) 0.0195(10) 0.0200(9) 0.0009(8) 0.0046(7) -0.0011(8) C9B 0.0166(9) 0.0190(10) 0.0301(10) 0.0000(9) 0.0042(7) -0.0008(8) C10B 0.0177(9) 0.0205(10) 0.0279(10) 0.0061(9) -0.0037(7) -0.0006(8) C11B 0.0226(10) 0.0220(11) 0.0180(9) 0.0014(8) -0.0030(7) -0.0063(8) C12B 0.0194(8) 0.0196(10) 0.0171(9) -0.0026(8) 0.0024(7) -0.0033(8) C3AB 0.0133(8) 0.0192(10) 0.0178(8) 0.0002(8) 0.0050(6) -0.0006(8) C2'B 0.0186(9) 0.0171(10) 0.0136(8) 0.0014(7) 0.0042(7) 0.0007(7) C3'B 0.0165(8) 0.0219(11) 0.0189(9) 0.0023(8) 0.0049(7) 0.0009(8) C4'B 0.0153(8) 0.0214(10) 0.0212(9) 0.0014(8) 0.0060(7) 0.0034(8) C5'B 0.0176(9) 0.0190(10) 0.0208(9) 0.0011(8) 0.0047(7) 0.0042(8) C6'B 0.0181(9) 0.0149(9) 0.0165(8) 0.0008(7) 0.0029(7) 0.0007(7) _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 O1A C2'A 1.434(2) . ? O1A NA 1.4838(19) . ? O2A C6A 1.432(2) . ? O2A HO2A 0.82(3) . ? NA C1A 1.480(2) . ? NA C3AA 1.487(2) . ? C1A C6'A 1.536(3) . ? C1A C5A 1.540(2) . ? C1A C2A 1.552(3) . ? C2A C6A 1.529(3) . ? C2A C3A 1.550(3) . ? C2A H2A 0.9800 . ? C3A C4A 1.544(3) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A C5A 1.541(3) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C7A C12A 1.394(3) . ? C7A C8A 1.395(3) . ? C7A C2'A 1.517(3) . ? C8A C9A 1.390(3) . ? C8A H8A 0.9300 . ? C9A C10A 1.389(3) . ? C9A H9A 0.9300 . ? C10A C11A 1.395(3) . ? C10A H10A 0.9300 . ? C11A C12A 1.396(3) . ? C11A H11A 0.9300 . ? C12A H12A 0.9300 . ? C3AA C3'A 1.536(2) . ? C3AA C4'A 1.538(3) . ? C3AA H3AA 0.9800 . ? C2'A C3'A 1.556(3) . ? C2'A H2'A 0.9800 . ? C3'A H3'1 0.9700 . ? C3'A H3'2 0.9700 . ? C4'A C5'A 1.524(3) . ? C4'A H4'1 0.9700 . ? C4'A H4'2 0.9700 . ? C5'A C6'A 1.530(3) . ? C5'A H5'1 0.9700 . ? C5'A H5'2 0.9700 . ? C6'A H6'1 0.9700 . ? C6'A H6'2 0.9700 . ? O1B C2'B 1.444(2) . ? O1B NB 1.4830(19) . ? O2B C6B 1.444(2) . ? O2B HO2B 0.82(3) . ? NB C1B 1.491(2) . ? NB C3AB 1.494(2) . ? C1B C6'B 1.540(3) . ? C1B C5B 1.543(2) . ? C1B C2B 1.583(3) . ? C2B C6B 1.527(3) . ? C2B C3B 1.550(2) . ? C2B H2B 0.9800 . ? C3B C4B 1.522(3) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B C5B 1.529(2) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C7B C8B 1.396(3) . ? C7B C12B 1.397(2) . ? C7B C2'B 1.517(3) . ? C8B C9B 1.390(3) . ? C8B H8B 0.9300 . ? C9B C10B 1.392(3) . ? C9B H9B 0.9300 . ? C10B C11B 1.395(3) . ? C10B H10B 0.9300 . ? C11B C12B 1.391(3) . ? C11B H11B 0.9300 . ? C12B H12B 0.9300 . ? C3AB C4'B 1.529(3) . ? C3AB C3'B 1.532(2) . ? C3AB H3AB 0.9800 . ? C2'B C3'B 1.547(3) . ? C2'B H2'B 0.9800 . ? C3'B H3'3 0.9700 . ? C3'B H3'4 0.9700 . ? C4'B C5'B 1.529(3) . ? C4'B H4'3 0.9700 . ? C4'B H4'4 0.9700 . ? C5'B C6'B 1.532(2) . ? C5'B H5'3 0.9700 . ? C5'B H5'4 0.9700 . ? C6'B H6'3 0.9700 . ? C6'B H6'4 0.9700 . ? 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'A O1A NA 103.07(12) . . ? C6A O2A HO2A 108.1(17) . . ? C1A NA O1A 106.39(13) . . ? C1A NA C3AA 116.08(14) . . ? O1A NA C3AA 100.46(13) . . ? NA C1A C6'A 112.71(15) . . ? NA C1A C5A 109.36(14) . . ? C6'A C1A C5A 110.46(16) . . ? NA C1A C2A 109.32(15) . . ? C6'A C1A C2A 111.64(15) . . ? C5A C1A C2A 102.90(15) . . ? C6A C2A C3A 110.96(16) . . ? C6A C2A C1A 113.23(15) . . ? C3A C2A C1A 103.37(15) . . ? C6A C2A H2A 109.7 . . ? C3A C2A H2A 109.7 . . ? C1A C2A H2A 109.7 . . ? C4A C3A C2A 106.33(15) . . ? C4A C3A H3A1 110.5 . . ? C2A C3A H3A1 110.5 . . ? C4A C3A H3A2 110.5 . . ? C2A C3A H3A2 110.5 . . ? H3A1 C3A H3A2 108.7 . . ? C5A C4A C3A 106.41(15) . . ? C5A C4A H4A1 110.4 . . ? C3A C4A H4A1 110.4 . . ? C5A C4A H4A2 110.4 . . ? C3A C4A H4A2 110.4 . . ? H4A1 C4A H4A2 108.6 . . ? C1A C5A C4A 105.21(15) . . ? C1A C5A H5A1 110.7 . . ? C4A C5A H5A1 110.7 . . ? C1A C5A H5A2 110.7 . . ? C4A C5A H5A2 110.7 . . ? H5A1 C5A H5A2 108.8 . . ? O2A C6A C2A 112.10(15) . . ? O2A C6A H6A1 109.2 . . ? C2A C6A H6A1 109.2 . . ? O2A C6A H6A2 109.2 . . ? C2A C6A H6A2 109.2 . . ? H6A1 C6A H6A2 107.9 . . ? C12A C7A C8A 118.70(18) . . ? C12A C7A C2'A 122.00(16) . . ? C8A C7A C2'A 119.30(17) . . ? C9A C8A C7A 120.92(18) . . ? C9A C8A H8A 119.5 . . ? C7A C8A H8A 119.5 . . ? C10A C9A C8A 120.15(18) . . ? C10A C9A H9A 119.9 . . ? C8A C9A H9A 119.9 . . ? C9A C10A C11A 119.51(19) . . ? C9A C10A H10A 120.2 . . ? C11A C10A H10A 120.2 . . ? C10A C11A C12A 120.12(18) . . ? C10A C11A H11A 119.9 . . ? C12A C11A H11A 119.9 . . ? C7A C12A C11A 120.59(17) . . ? C7A C12A H12A 119.7 . . ? C11A C12A H12A 119.7 . . ? NA C3AA C3'A 99.70(14) . . ? NA C3AA C4'A 114.46(15) . . ? C3'A C3AA C4'A 112.76(16) . . ? NA C3AA H3AA 109.8 . . ? C3'A C3AA H3AA 109.8 . . ? C4'A C3AA H3AA 109.8 . . ? O1A C2'A C7A 112.15(15) . . ? O1A C2'A C3'A 105.80(14) . . ? C7A C2'A C3'A 112.76(16) . . ? O1A C2'A H2'A 108.7 . . ? C7A C2'A H2'A 108.7 . . ? C3'A C2'A H2'A 108.7 . . ? C3AA C3'A C2'A 102.53(14) . . ? C3AA C3'A H3'1 111.3 . . ? C2'A C3'A H3'1 111.3 . . ? C3AA C3'A H3'2 111.3 . . ? C2'A C3'A H3'2 111.3 . . ? H3'1 C3'A H3'2 109.2 . . ? C5'A C4'A C3AA 111.58(16) . . ? C5'A C4'A H4'1 109.3 . . ? C3AA C4'A H4'1 109.3 . . ? C5'A C4'A H4'2 109.3 . . ? C3AA C4'A H4'2 109.3 . . ? H4'1 C4'A H4'2 108.0 . . ? C4'A C5'A C6'A 109.75(15) . . ? C4'A C5'A H5'1 109.7 . . ? C6'A C5'A H5'1 109.7 . . ? C4'A C5'A H5'2 109.7 . . ? C6'A C5'A H5'2 109.7 . . ? H5'1 C5'A H5'2 108.2 . . ? C5'A C6'A C1A 112.58(16) . . ? C5'A C6'A H6'1 109.1 . . ? C1A C6'A H6'1 109.1 . . ? C5'A C6'A H6'2 109.1 . . ? C1A C6'A H6'2 109.1 . . ? H6'1 C6'A H6'2 107.8 . . ? C2'B O1B NB 106.13(12) . . ? C6B O2B HO2B 102.9(16) . . ? O1B NB C1B 104.96(13) . . ? O1B NB C3AB 101.43(12) . . ? C1B NB C3AB 117.34(14) . . ? NB C1B C6'B 112.19(15) . . ? NB C1B C5B 108.92(14) . . ? C6'B C1B C5B 110.07(15) . . ? NB C1B C2B 110.55(15) . . ? C6'B C1B C2B 111.21(14) . . ? C5B C1B C2B 103.53(14) . . ? C6B C2B C3B 110.82(16) . . ? C6B C2B C1B 117.16(15) . . ? C3B C2B C1B 105.38(14) . . ? C6B C2B H2B 107.7 . . ? C3B C2B H2B 107.7 . . ? C1B C2B H2B 107.7 . . ? C4B C3B C2B 106.25(15) . . ? C4B C3B H3B1 110.5 . . ? C2B C3B H3B1 110.5 . . ? C4B C3B H3B2 110.5 . . ? C2B C3B H3B2 110.5 . . ? H3B1 C3B H3B2 108.7 . . ? C3B C4B C5B 102.28(15) . . ? C3B C4B H4B1 111.3 . . ? C5B C4B H4B1 111.3 . . ? C3B C4B H4B2 111.3 . . ? C5B C4B H4B2 111.3 . . ? H4B1 C4B H4B2 109.2 . . ? C4B C5B C1B 104.35(14) . . ? C4B C5B H5B1 110.9 . . ? C1B C5B H5B1 110.9 . . ? C4B C5B H5B2 110.9 . . ? C1B C5B H5B2 110.9 . . ? H5B1 C5B H5B2 108.9 . . ? O2B C6B C2B 112.98(15) . . ? O2B C6B H6B1 109.0 . . ? C2B C6B H6B1 109.0 . . ? O2B C6B H6B2 109.0 . . ? C2B C6B H6B2 109.0 . . ? H6B1 C6B H6B2 107.8 . . ? C8B C7B C12B 118.93(17) . . ? C8B C7B C2'B 122.26(15) . . ? C12B C7B C2'B 118.74(16) . . ? C9B C8B C7B 120.46(17) . . ? C9B C8B H8B 119.8 . . ? C7B C8B H8B 119.8 . . ? C8B C9B C10B 120.39(19) . . ? C8B C9B H9B 119.8 . . ? C10B C9B H9B 119.8 . . ? C9B C10B C11B 119.46(19) . . ? C9B C10B H10B 120.3 . . ? C11B C10B H10B 120.3 . . ? C12B C11B C10B 120.12(18) . . ? C12B C11B H11B 119.9 . . ? C10B C11B H11B 119.9 . . ? C11B C12B C7B 120.64(19) . . ? C11B C12B H12B 119.7 . . ? C7B C12B H12B 119.7 . . ? NB C3AB C4'B 114.76(16) . . ? NB C3AB C3'B 99.86(14) . . ? C4'B C3AB C3'B 112.85(16) . . ? NB C3AB H3AB 109.7 . . ? C4'B C3AB H3AB 109.7 . . ? C3'B C3AB H3AB 109.7 . . ? O1B C2'B C7B 111.58(14) . . ? O1B C2'B C3'B 105.66(14) . . ? C7B C2'B C3'B 112.77(16) . . ? O1B C2'B H2'B 108.9 . . ? C7B C2'B H2'B 108.9 . . ? C3'B C2'B H2'B 108.9 . . ? C3AB C3'B C2'B 102.86(15) . . ? C3AB C3'B H3'3 111.2 . . ? C2'B C3'B H3'3 111.2 . . ? C3AB C3'B H3'4 111.2 . . ? C2'B C3'B H3'4 111.2 . . ? H3'3 C3'B H3'4 109.1 . . ? C3AB C4'B C5'B 110.53(16) . . ? C3AB C4'B H4'3 109.5 . . ? C5'B C4'B H4'3 109.5 . . ? C3AB C4'B H4'4 109.5 . . ? C5'B C4'B H4'4 109.5 . . ? H4'3 C4'B H4'4 108.1 . . ? C4'B C5'B C6'B 108.81(15) . . ? C4'B C5'B H5'3 109.9 . . ? C6'B C5'B H5'3 109.9 . . ? C4'B C5'B H5'4 109.9 . . ? C6'B C5'B H5'4 109.9 . . ? H5'3 C5'B H5'4 108.3 . . ? C5'B C6'B C1B 112.12(16) . . ? C5'B C6'B H6'3 109.2 . . ? C1B C6'B H6'3 109.2 . . ? C5'B C6'B H6'4 109.2 . . ? C1B C6'B H6'4 109.2 . . ? H6'3 C6'B H6'4 107.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2A HO2A O2B 0.82(3) 2.01(3) 2.817(2) 168(2) 1_465 O2B HO2B NB 0.82(3) 2.00(3) 2.712(2) 144(2) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.210 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.039 #===END data_yshr99 _database_code_depnum_ccdc_archive 'CCDC 725421' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H27 N O3' _chemical_formula_sum 'C18 H27 N O3' _chemical_formula_weight 305.41 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 _symmetry_space_group_name_Hall -p_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2552(1) _cell_length_b 10.5282(2) _cell_length_c 13.4329(2) _cell_angle_alpha 104.454(1) _cell_angle_beta 101.796(1) _cell_angle_gamma 97.250(1) _cell_volume 823.76(2) _cell_formula_units_Z 2 _cell_measurement_temperature 84(2) _cell_measurement_reflns_used 4948 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 26.30 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Sheldrick, 1997' _exptl_absorpt_correction_T_min 0.9661 _exptl_absorpt_correction_T_max 0.9853 _diffrn_ambient_temperature 84(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method 'Area detector \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% <2 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _reflns_threshold_expression I>2\s(I) _diffrn_reflns_number 7744 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 26.30 _reflns_number_total 3258 _reflns_number_gt 2529 _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT (Bruker, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0976P)^2^+0.1252P] 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 3258 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1440 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 -0.2952(2) 0.84613(13) 0.87510(10) 0.0239(3) Uani 1 1 d . . . HO1 H -0.2585 0.9240 0.9118 0.054(8) Uiso 1 1 calc R . . O2 O -0.1495(2) 0.61750(12) 0.89416(10) 0.0221(3) Uani 1 1 d . . . HO2 H -0.2218 0.6738 0.9153 0.063(9) Uiso 1 1 calc R . . O3 O 0.1924(2) 0.88216(12) 1.03140(10) 0.0232(3) Uani 1 1 d . . . HO3 H 0.1135 0.8480 0.9713 0.028(6) Uiso 1 1 calc R . . N N 0.0189(2) 0.67575(14) 0.84817(11) 0.0167(3) Uani 1 1 d . . . C1 C -0.2895(3) 0.69639(17) 0.70235(14) 0.0192(4) Uani 1 1 d . . . H1A H -0.4200 0.6375 0.7063 0.023 Uiso 1 1 calc R . . C2 C -0.3060(3) 0.69682(19) 0.58541(14) 0.0245(4) Uani 1 1 d . . . H2A H -0.4040 0.6168 0.5371 0.029 Uiso 1 1 calc R . . H2B H -0.3636 0.7740 0.5723 0.029 Uiso 1 1 calc R . . C3 C -0.0663(3) 0.70193(19) 0.56958(14) 0.0249(4) Uani 1 1 d . . . H3A H -0.0599 0.6246 0.5139 0.030 Uiso 1 1 calc R . . H3B H -0.0186 0.7818 0.5503 0.030 Uiso 1 1 calc R . . C4 C 0.0835(3) 0.70285(18) 0.67685(14) 0.0197(4) Uani 1 1 d . . . H4A H 0.1507 0.7934 0.7194 0.024 Uiso 1 1 calc R . . H4B H 0.2003 0.6524 0.6660 0.024 Uiso 1 1 calc R . . C5 C -0.0767(3) 0.63624(16) 0.73089(13) 0.0172(4) Uani 1 1 d . . . C7 C 0.2201(3) 0.61758(17) 0.87775(13) 0.0190(4) Uani 1 1 d . . . H7A H 0.3328 0.6534 0.8458 0.023 Uiso 1 1 calc R . . C8 C 0.1776(3) 0.46435(18) 0.83407(14) 0.0238(4) Uani 1 1 d . . . H8A H 0.3168 0.4331 0.8491 0.029 Uiso 1 1 calc R . . H8B H 0.0778 0.4250 0.8694 0.029 Uiso 1 1 calc R . . C9 C 0.0752(3) 0.41899(17) 0.71367(14) 0.0222(4) Uani 1 1 d . . . H9A H 0.0317 0.3225 0.6900 0.027 Uiso 1 1 calc R . . H9B H 0.1854 0.4444 0.6774 0.027 Uiso 1 1 calc R . . C10 C -0.1294(3) 0.48219(17) 0.68494(14) 0.0201(4) Uani 1 1 d . . . H10A H -0.2479 0.4457 0.7122 0.024 Uiso 1 1 calc R . . H10B H -0.1812 0.4592 0.6084 0.024 Uiso 1 1 calc R . . C11 C 0.4884(3) 0.85268(16) 1.16516(14) 0.0187(4) Uani 1 1 d . . . C12 C 0.3600(3) 0.83530(18) 1.23625(14) 0.0228(4) Uani 1 1 d . . . H12A H 0.2079 0.8028 1.2111 0.027 Uiso 1 1 calc R . . C13 C 0.4583(3) 0.86632(18) 1.34502(15) 0.0248(4) Uani 1 1 d . . . H13A H 0.3716 0.8545 1.3917 0.030 Uiso 1 1 calc R . . C14 C 0.6869(3) 0.91502(18) 1.38324(14) 0.0240(4) Uani 1 1 d . . . H14A H 0.7523 0.9367 1.4555 0.029 Uiso 1 1 calc R . . C15 C 0.8159(3) 0.93097(18) 1.31287(15) 0.0249(4) Uani 1 1 d . . . H15A H 0.9682 0.9625 1.3381 0.030 Uiso 1 1 calc R . . C16 C 0.7181(3) 0.89992(17) 1.20441(15) 0.0221(4) Uani 1 1 d . . . H16A H 0.8059 0.9106 1.1579 0.027 Uiso 1 1 calc R . . C1' C -0.2803(3) 0.83918(17) 0.76879(14) 0.0209(4) Uani 1 1 d . . . H1'A H -0.1421 0.8945 0.7711 0.025 Uiso 1 1 calc R . . H1'B H -0.4016 0.8748 0.7348 0.025 Uiso 1 1 calc R . . C2' C 0.3156(3) 0.66442(17) 0.99861(13) 0.0208(4) Uani 1 1 d . . . H2'A H 0.2057 0.6311 1.0320 0.025 Uiso 1 1 calc R . . H2'B H 0.4452 0.6247 1.0156 0.025 Uiso 1 1 calc R . . C3' C 0.3827(3) 0.81656(17) 1.04663(14) 0.0200(4) Uani 1 1 d . . . H3'A H 0.4913 0.8507 1.0118 0.024 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 0.0326(7) 0.0150(7) 0.0274(7) 0.0070(5) 0.0117(6) 0.0076(6) O2 0.0278(7) 0.0169(6) 0.0274(7) 0.0112(5) 0.0128(6) 0.0048(6) O3 0.0311(7) 0.0151(7) 0.0204(7) 0.0046(5) -0.0024(6) 0.0093(5) N 0.0182(7) 0.0146(7) 0.0200(8) 0.0085(6) 0.0058(6) 0.0041(6) C1 0.0183(9) 0.0142(9) 0.0246(9) 0.0068(7) 0.0021(7) 0.0033(7) C2 0.0300(10) 0.0201(9) 0.0221(9) 0.0073(7) -0.0009(8) 0.0089(8) C3 0.0335(11) 0.0234(10) 0.0205(9) 0.0111(7) 0.0046(8) 0.0088(8) C4 0.0220(9) 0.0173(9) 0.0205(9) 0.0072(7) 0.0039(7) 0.0052(7) C5 0.0197(9) 0.0123(9) 0.0201(9) 0.0060(7) 0.0030(7) 0.0048(7) C7 0.0243(9) 0.0161(9) 0.0182(9) 0.0072(7) 0.0030(7) 0.0083(7) C8 0.0339(10) 0.0154(9) 0.0221(9) 0.0062(7) 0.0014(8) 0.0117(8) C9 0.0303(10) 0.0133(9) 0.0232(9) 0.0051(7) 0.0043(8) 0.0083(7) C10 0.0235(9) 0.0134(9) 0.0221(9) 0.0052(7) 0.0021(7) 0.0045(7) C11 0.0267(9) 0.0089(8) 0.0210(9) 0.0058(6) 0.0035(7) 0.0063(7) C12 0.0252(9) 0.0176(9) 0.0255(10) 0.0074(7) 0.0029(8) 0.0065(7) C13 0.0359(11) 0.0180(9) 0.0238(10) 0.0098(7) 0.0087(8) 0.0075(8) C14 0.0358(11) 0.0146(9) 0.0194(9) 0.0064(7) -0.0012(8) 0.0064(8) C15 0.0263(10) 0.0160(9) 0.0284(10) 0.0067(7) -0.0023(8) 0.0031(7) C16 0.0275(10) 0.0137(9) 0.0263(10) 0.0073(7) 0.0066(8) 0.0049(7) C1' 0.0218(9) 0.0160(9) 0.0260(9) 0.0084(7) 0.0044(7) 0.0058(7) C2' 0.0274(9) 0.0153(9) 0.0198(9) 0.0061(7) 0.0011(7) 0.0099(7) C3' 0.0243(9) 0.0159(9) 0.0205(9) 0.0070(7) 0.0028(7) 0.0071(7) _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' 1.434(2) . ? O1 HO1 0.8200 . ? O2 N 1.4695(18) . ? O2 HO2 0.8200 . ? O3 C3' 1.454(2) . ? O3 HO3 0.8200 . ? N C7 1.493(2) . ? N C5 1.496(2) . ? C1 C1' 1.532(2) . ? C1 C2 1.554(2) . ? C1 C5 1.564(2) . ? C1 H1A 0.9800 . ? C2 C3 1.553(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.547(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.548(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C10 1.550(2) . ? C7 C2' 1.538(2) . ? C7 C8 1.540(2) . ? C7 H7A 0.9800 . ? C8 C9 1.539(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.540(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.398(3) . ? C11 C16 1.403(3) . ? C11 C3' 1.523(2) . ? C12 C13 1.401(3) . ? C12 H12A 0.9300 . ? C13 C14 1.398(3) . ? C13 H13A 0.9300 . ? C14 C15 1.389(3) . ? C14 H14A 0.9300 . ? C15 C16 1.397(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C1' H1'A 0.9700 . ? C1' H1'B 0.9700 . ? C2' C3' 1.537(2) . ? C2' H2'A 0.9700 . ? C2' H2'B 0.9700 . ? C3' H3'A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1' O1 HO1 109.5 . . ? N O2 HO2 109.5 . . ? C3' O3 HO3 109.5 . . ? O2 N C7 106.06(12) . . ? O2 N C5 106.68(12) . . ? C7 N C5 112.36(13) . . ? C1' C1 C2 108.50(14) . . ? C1' C1 C5 115.49(14) . . ? C2 C1 C5 103.43(14) . . ? C1' C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? C5 C1 H1A 109.7 . . ? C3 C2 C1 106.30(14) . . ? C3 C2 H2A 110.5 . . ? C1 C2 H2A 110.5 . . ? C3 C2 H2B 110.5 . . ? C1 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? C4 C3 C2 106.23(15) . . ? C4 C3 H3A 110.5 . . ? C2 C3 H3A 110.5 . . ? C4 C3 H3B 110.5 . . ? C2 C3 H3B 110.5 . . ? H3A C3 H3B 108.7 . . ? C3 C4 C5 104.29(14) . . ? C3 C4 H4A 110.9 . . ? C5 C4 H4A 110.9 . . ? C3 C4 H4B 110.9 . . ? C5 C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? N C5 C4 110.02(13) . . ? N C5 C10 110.74(13) . . ? C4 C5 C10 111.88(14) . . ? N C5 C1 111.25(13) . . ? C4 C5 C1 102.18(13) . . ? C10 C5 C1 110.50(13) . . ? N C7 C2' 110.28(14) . . ? N C7 C8 113.00(14) . . ? C2' C7 C8 111.88(14) . . ? N C7 H7A 107.1 . . ? C2' C7 H7A 107.1 . . ? C8 C7 H7A 107.1 . . ? C9 C8 C7 111.21(14) . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C10 111.08(14) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C5 112.01(14) . . ? C9 C10 H10A 109.2 . . ? C5 C10 H10A 109.2 . . ? C9 C10 H10B 109.2 . . ? C5 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C16 118.85(16) . . ? C12 C11 C3' 120.72(16) . . ? C16 C11 C3' 120.39(16) . . ? C11 C12 C13 120.60(17) . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C14 C13 C12 119.96(18) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C15 C14 C13 119.73(17) . . ? C15 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? C14 C15 C16 120.37(18) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C15 C16 C11 120.48(18) . . ? C15 C16 H16A 119.8 . . ? C11 C16 H16A 119.8 . . ? O1 C1' C1 112.60(14) . . ? O1 C1' H1'A 109.1 . . ? C1 C1' H1'A 109.1 . . ? O1 C1' H1'B 109.1 . . ? C1 C1' H1'B 109.1 . . ? H1'A C1' H1'B 107.8 . . ? C3' C2' C7 114.88(14) . . ? C3' C2' H2'A 108.5 . . ? C7 C2' H2'A 108.5 . . ? C3' C2' H2'B 108.5 . . ? C7 C2' H2'B 108.5 . . ? H2'A C2' H2'B 107.5 . . ? O3 C3' C11 108.16(13) . . ? O3 C3' C2' 111.62(14) . . ? C11 C3' C2' 110.98(14) . . ? O3 C3' H3'A 108.7 . . ? C11 C3' H3'A 108.7 . . ? C2' C3' H3'A 108.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 HO1 O3 0.82 1.95 2.7543(18) 167.0 2_577 O2 HO2 O1 0.82 2.10 2.7307(18) 134.1 . O3 HO3 N 0.82 2.05 2.7570(19) 144.0 . _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 26.30 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.424 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.070