# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email vmereddy@d.umn.edu _publ_contact_author_name V.Mereddy loop_ _publ_author_name S.Tekkam M.Alam S.Jonnalagadda V.Mereddy data_09099c _database_code_depnum_ccdc_archive 'CCDC 805099' #TrackingRef '- 09099c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 09099c _chemical_melting_point ? _chemical_formula_moiety 'C10 H15 N O3' _chemical_formula_sum 'C10 H15 N O3' _chemical_formula_weight 197.23 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 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 6.157(3) _cell_length_b 19.220(8) _cell_length_c 9.096(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.386(6) _cell_angle_gamma 90.00 _cell_volume 1071.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2969 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.58 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9563 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2008)' _exptl_special_details 'Prof. V. Mereddy - UMD' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 3398 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.43 _reflns_number_total 2192 _reflns_number_gt 1832 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0727P)^2^+0.4394P] 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 2192 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1436 _refine_ls_wR_factor_gt 0.1340 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.003 _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 C1 C 0.3698(3) 0.64738(9) 0.63896(19) 0.0233(4) Uani 1 1 d . . . N1 N 0.3958(3) 0.57963(8) 0.57061(16) 0.0247(4) Uani 1 1 d . . . H1A H 0.512(4) 0.5532(12) 0.589(2) 0.030 Uiso 1 1 d . . . C2 C 0.2338(3) 0.56235(10) 0.46680(18) 0.0238(4) Uani 1 1 d . . . O1 O 0.2317(2) 0.50977(7) 0.38862(14) 0.0308(4) Uani 1 1 d . . . C3 C 0.0532(3) 0.61667(10) 0.4628(2) 0.0253(4) Uani 1 1 d . . . H3A H -0.0691 0.5963 0.5137 0.030 Uiso 1 1 calc R . . C4 C -0.0381(4) 0.63618(12) 0.3061(2) 0.0393(6) Uani 1 1 d . . . H4A H -0.1670 0.6658 0.3104 0.059 Uiso 1 1 calc R . . H4B H -0.0789 0.5938 0.2503 0.059 Uiso 1 1 calc R . . H4C H 0.0732 0.6615 0.2572 0.059 Uiso 1 1 calc R . . C5 C 0.1527(3) 0.67493(10) 0.5594(2) 0.0250(4) Uani 1 1 d . . . H5A H 0.0515 0.6965 0.6261 0.030 Uiso 1 1 calc R . . O2 O 0.2792(3) 0.72558(7) 0.47739(16) 0.0351(4) Uani 1 1 d . . . C6 C 0.4723(4) 0.70452(10) 0.5500(2) 0.0286(4) Uani 1 1 d . . . O3 O 0.6501(3) 0.72732(8) 0.53696(18) 0.0415(4) Uani 1 1 d . . . C7 C 0.4272(3) 0.64946(10) 0.8049(2) 0.0280(4) Uani 1 1 d . . . H7A H 0.3818 0.6952 0.8417 0.034 Uiso 1 1 calc R . . H7B H 0.5878 0.6465 0.8245 0.034 Uiso 1 1 calc R . . C8 C 0.3262(4) 0.59258(11) 0.8943(2) 0.0338(5) Uani 1 1 d . . . H8A H 0.3679 0.5464 0.8547 0.041 Uiso 1 1 calc R . . C9 C 0.0787(4) 0.59661(13) 0.8835(2) 0.0411(6) Uani 1 1 d . . . H9A H 0.0197 0.5892 0.7809 0.062 Uiso 1 1 calc R . . H9B H 0.0342 0.6426 0.9164 0.062 Uiso 1 1 calc R . . H9C H 0.0225 0.5607 0.9464 0.062 Uiso 1 1 calc R . . C10 C 0.4239(5) 0.59788(16) 1.0558(2) 0.0517(7) Uani 1 1 d . . . H10A H 0.5819 0.5905 1.0610 0.077 Uiso 1 1 calc R . . H10B H 0.3579 0.5624 1.1150 0.077 Uiso 1 1 calc R . . H10C H 0.3941 0.6442 1.0945 0.077 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 C1 0.0234(10) 0.0203(9) 0.0264(9) -0.0030(7) 0.0030(7) 0.0015(7) N1 0.0259(9) 0.0216(8) 0.0262(8) -0.0036(6) 0.0006(7) 0.0048(7) C2 0.0275(11) 0.0223(9) 0.0216(8) 0.0014(7) 0.0028(7) -0.0005(8) O1 0.0368(9) 0.0257(7) 0.0290(7) -0.0071(6) -0.0013(6) 0.0025(6) C3 0.0232(10) 0.0278(10) 0.0246(9) -0.0009(8) 0.0011(7) 0.0017(7) C4 0.0437(14) 0.0432(13) 0.0290(10) -0.0047(9) -0.0070(9) 0.0142(10) C5 0.0222(10) 0.0237(10) 0.0294(9) 0.0007(7) 0.0037(8) -0.0004(7) O2 0.0334(9) 0.0284(8) 0.0431(8) 0.0090(6) 0.0014(7) -0.0005(6) C6 0.0290(11) 0.0231(10) 0.0342(10) -0.0041(8) 0.0050(8) 0.0019(8) O3 0.0327(9) 0.0367(9) 0.0569(10) 0.0003(7) 0.0136(7) -0.0068(7) C7 0.0260(11) 0.0293(10) 0.0279(9) -0.0061(8) -0.0013(8) 0.0028(8) C8 0.0468(14) 0.0296(11) 0.0251(9) -0.0011(8) 0.0033(9) 0.0075(9) C9 0.0480(15) 0.0446(13) 0.0309(10) 0.0002(9) 0.0051(10) -0.0132(11) C10 0.0577(17) 0.0676(18) 0.0286(11) 0.0063(11) -0.0020(11) 0.0168(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 C1 N1 1.458(2) . ? C1 C7 1.518(3) . ? C1 C6 1.535(3) . ? C1 C5 1.552(3) . ? N1 C2 1.349(2) . ? N1 H1A 0.88(2) . ? C2 O1 1.235(2) . ? C2 C3 1.523(3) . ? C3 C5 1.517(3) . ? C3 C4 1.529(3) . ? C3 H3A 1.0000 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 O2 1.490(2) . ? C5 H5A 1.0000 . ? O2 C6 1.366(3) . ? C6 O3 1.195(3) . ? C7 C8 1.529(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.520(3) . ? C8 C10 1.538(3) . ? C8 H8A 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 N1 C1 C7 115.01(15) . . ? N1 C1 C6 110.31(15) . . ? C7 C1 C6 115.87(16) . . ? N1 C1 C5 103.30(15) . . ? C7 C1 C5 124.36(16) . . ? C6 C1 C5 83.63(14) . . ? C2 N1 C1 114.50(16) . . ? C2 N1 H1A 121.8(15) . . ? C1 N1 H1A 123.5(15) . . ? O1 C2 N1 124.86(18) . . ? O1 C2 C3 125.39(17) . . ? N1 C2 C3 109.75(16) . . ? C5 C3 C2 103.77(15) . . ? C5 C3 C4 116.88(17) . . ? C2 C3 C4 113.19(16) . . ? C5 C3 H3A 107.5 . . ? C2 C3 H3A 107.5 . . ? C4 C3 H3A 107.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C3 113.19(15) . . ? O2 C5 C1 89.35(14) . . ? C3 C5 C1 107.55(15) . . ? O2 C5 H5A 114.7 . . ? C3 C5 H5A 114.7 . . ? C1 C5 H5A 114.7 . . ? C6 O2 C5 92.09(14) . . ? O3 C6 O2 127.37(19) . . ? O3 C6 C1 137.8(2) . . ? O2 C6 C1 94.83(16) . . ? C1 C7 C8 116.18(16) . . ? C1 C7 H7A 108.2 . . ? C8 C7 H7A 108.2 . . ? C1 C7 H7B 108.2 . . ? C8 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? C9 C8 C7 112.64(17) . . ? C9 C8 C10 110.97(18) . . ? C7 C8 C10 108.6(2) . . ? C9 C8 H8A 108.2 . . ? C7 C8 H8A 108.2 . . ? C10 C8 H8A 108.2 . . ? 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 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C1 N1 C2 138.23(17) . . . . ? C6 C1 N1 C2 -88.5(2) . . . . ? C5 C1 N1 C2 -0.4(2) . . . . ? C1 N1 C2 O1 174.68(17) . . . . ? C1 N1 C2 C3 -6.3(2) . . . . ? O1 C2 C3 C5 -170.80(17) . . . . ? N1 C2 C3 C5 10.20(19) . . . . ? O1 C2 C3 C4 -43.1(3) . . . . ? N1 C2 C3 C4 137.90(18) . . . . ? C2 C3 C5 O2 86.87(18) . . . . ? C4 C3 C5 O2 -38.5(2) . . . . ? C2 C3 C5 C1 -10.16(18) . . . . ? C4 C3 C5 C1 -135.54(18) . . . . ? N1 C1 C5 O2 -107.28(14) . . . . ? C7 C1 C5 O2 119.25(18) . . . . ? C6 C1 C5 O2 2.15(13) . . . . ? N1 C1 C5 C3 6.89(18) . . . . ? C7 C1 C5 C3 -126.59(18) . . . . ? C6 C1 C5 C3 116.31(15) . . . . ? C3 C5 O2 C6 -111.25(17) . . . . ? C1 C5 O2 C6 -2.40(14) . . . . ? C5 O2 C6 O3 -178.1(2) . . . . ? C5 O2 C6 C1 2.43(15) . . . . ? N1 C1 C6 O3 -79.9(3) . . . . ? C7 C1 C6 O3 53.0(3) . . . . ? C5 C1 C6 O3 178.2(3) . . . . ? N1 C1 C6 O2 99.52(17) . . . . ? C7 C1 C6 O2 -127.59(17) . . . . ? C5 C1 C6 O2 -2.35(14) . . . . ? N1 C1 C7 C8 -49.1(2) . . . . ? C6 C1 C7 C8 -179.83(17) . . . . ? C5 C1 C7 C8 79.7(2) . . . . ? C1 C7 C8 C9 -63.4(2) . . . . ? C1 C7 C8 C10 173.30(18) . . . . ? 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 N1 H1A O1 0.88(2) 1.99(3) 2.862(2) 174(2) 3_666 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.291 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.056 # Attachment '- 10098A.cif' data_10098a _database_code_depnum_ccdc_archive 'CCDC 805100' #TrackingRef '- 10098A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 10098 _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 N O3' _chemical_formula_sum 'C17 H21 N O3' _chemical_formula_weight 287.35 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 7.5860(5) _cell_length_b 7.8370(6) _cell_length_c 13.2647(9) _cell_angle_alpha 82.232(1) _cell_angle_beta 86.577(1) _cell_angle_gamma 78.360(1) _cell_volume 764.87(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3666 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.36 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9651 _exptl_absorpt_correction_T_max 0.9848 _exptl_absorpt_process_details 'SADABS (g. sHELDRICK, 2008)' _exptl_special_details 'Prof. V. Mereddy - UMD' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker, SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9154 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3456 _reflns_number_gt 2812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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^)+(0.0516P)^2^+0.1753P] 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 3456 _refine_ls_number_parameters 196 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 N1 N 0.55671(14) 0.63477(13) 0.58866(8) 0.0244(2) Uani 1 1 d D . . H1A H 0.5098(18) 0.5400(11) 0.5926(11) 0.029 Uiso 1 1 d D . . O1 O 0.57258(13) 0.68790(12) 0.41401(6) 0.0333(2) Uani 1 1 d . . . O2 O 0.32455(12) 0.69959(13) 0.75093(7) 0.0324(2) Uani 1 1 d . . . O3 O 0.54120(12) 0.76086(11) 0.84141(6) 0.0269(2) Uani 1 1 d . . . C1 C 0.62811(16) 0.68457(15) 0.67773(9) 0.0221(3) Uani 1 1 d . . . C2 C 0.60359(17) 0.71922(16) 0.49916(9) 0.0246(3) Uani 1 1 d . . . C3 C 0.69801(16) 0.85878(16) 0.52170(9) 0.0235(3) Uani 1 1 d . . . C4 C 0.67767(16) 0.86685(15) 0.63492(9) 0.0234(3) Uani 1 1 d . . . H4A H 0.5677 0.9581 0.6457 0.028 Uiso 1 1 calc R . . C5 C 0.77760(17) 0.95500(18) 0.45089(10) 0.0299(3) Uani 1 1 d . . . H5A H 0.7766 0.9370 0.3815 0.045 Uiso 1 1 calc R . . H5B H 0.8359 1.0423 0.4692 0.045 Uiso 1 1 calc R . . C6 C 0.83078(19) 0.91983(19) 0.68471(10) 0.0315(3) Uani 1 1 d . . . H6A H 0.8455 1.0370 0.6535 0.047 Uiso 1 1 calc R . . H6B H 0.9426 0.8351 0.6749 0.047 Uiso 1 1 calc R . . H6C H 0.8028 0.9215 0.7577 0.047 Uiso 1 1 calc R . . C7 C 0.47728(17) 0.71393(15) 0.75878(9) 0.0233(3) Uani 1 1 d . . . C8 C 0.41549(18) 0.79393(17) 0.92609(9) 0.0284(3) Uani 1 1 d . . . H8A H 0.4802 0.7572 0.9905 0.034 Uiso 1 1 calc R . . H8B H 0.3222 0.7219 0.9262 0.034 Uiso 1 1 calc R . . C9 C 0.32513(16) 0.98489(17) 0.92191(9) 0.0254(3) Uani 1 1 d . . . C10 C 0.21420(18) 1.03609(18) 1.00433(10) 0.0313(3) Uani 1 1 d . . . H10A H 0.1969 0.9512 1.0604 0.038 Uiso 1 1 calc R . . C11 C 0.12888(19) 1.2096(2) 1.00533(11) 0.0367(3) Uani 1 1 d . . . H11A H 0.0534 1.2433 1.0619 0.044 Uiso 1 1 calc R . . C12 C 0.15347(19) 1.33403(19) 0.92390(11) 0.0374(3) Uani 1 1 d . . . H12A H 0.0944 1.4530 0.9244 0.045 Uiso 1 1 calc R . . C13 C 0.26415(19) 1.28465(18) 0.84196(11) 0.0350(3) Uani 1 1 d . . . H13A H 0.2821 1.3700 0.7863 0.042 Uiso 1 1 calc R . . C14 C 0.34918(18) 1.11059(18) 0.84089(10) 0.0304(3) Uani 1 1 d . . . H14A H 0.4245 1.0773 0.7842 0.036 Uiso 1 1 calc R . . C15 C 0.78854(17) 0.54171(16) 0.72080(9) 0.0261(3) Uani 1 1 d . . . H15A H 0.8476 0.5920 0.7721 0.031 Uiso 1 1 calc R . . C16 C 0.9295(2) 0.4890(2) 0.63732(11) 0.0382(3) Uani 1 1 d . . . H16A H 1.0341 0.4085 0.6681 0.057 Uiso 1 1 calc R . . H16B H 0.9673 0.5941 0.6015 0.057 Uiso 1 1 calc R . . H16C H 0.8774 0.4305 0.5890 0.057 Uiso 1 1 calc R . . C17 C 0.7241(2) 0.37888(18) 0.77442(11) 0.0354(3) Uani 1 1 d . . . H17A H 0.8281 0.2900 0.7987 0.053 Uiso 1 1 calc R . . H17B H 0.6591 0.3313 0.7265 0.053 Uiso 1 1 calc R . . H17C H 0.6436 0.4110 0.8324 0.053 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 N1 0.0330(6) 0.0218(5) 0.0201(5) -0.0035(4) -0.0026(4) -0.0086(4) O1 0.0497(6) 0.0334(5) 0.0199(5) -0.0038(4) -0.0032(4) -0.0148(4) O2 0.0280(5) 0.0392(5) 0.0321(5) -0.0071(4) 0.0004(4) -0.0100(4) O3 0.0303(5) 0.0305(5) 0.0217(4) -0.0088(4) 0.0031(3) -0.0074(4) C1 0.0271(6) 0.0206(6) 0.0190(6) -0.0039(4) -0.0017(5) -0.0046(5) C2 0.0293(6) 0.0227(6) 0.0214(6) -0.0033(5) -0.0015(5) -0.0031(5) C3 0.0238(6) 0.0228(6) 0.0230(6) -0.0030(5) -0.0023(5) -0.0016(5) C4 0.0275(6) 0.0208(6) 0.0220(6) -0.0029(5) 0.0005(5) -0.0052(5) C5 0.0304(7) 0.0327(7) 0.0266(6) -0.0010(5) -0.0008(5) -0.0080(5) C6 0.0376(7) 0.0350(7) 0.0266(7) -0.0060(5) -0.0005(5) -0.0164(6) C7 0.0297(6) 0.0178(6) 0.0221(6) -0.0022(4) -0.0014(5) -0.0038(5) C8 0.0357(7) 0.0288(7) 0.0206(6) -0.0052(5) 0.0060(5) -0.0068(5) C9 0.0259(6) 0.0281(6) 0.0237(6) -0.0055(5) -0.0023(5) -0.0071(5) C10 0.0330(7) 0.0330(7) 0.0270(7) -0.0037(5) 0.0030(5) -0.0058(6) C11 0.0348(7) 0.0380(8) 0.0355(8) -0.0111(6) 0.0050(6) -0.0002(6) C12 0.0369(8) 0.0298(7) 0.0430(8) -0.0071(6) -0.0056(6) 0.0026(6) C13 0.0403(8) 0.0318(7) 0.0320(7) 0.0011(6) -0.0058(6) -0.0073(6) C14 0.0360(7) 0.0320(7) 0.0236(6) -0.0051(5) 0.0013(5) -0.0076(6) C15 0.0292(6) 0.0249(6) 0.0223(6) -0.0029(5) -0.0022(5) -0.0005(5) C16 0.0377(8) 0.0388(8) 0.0310(7) -0.0043(6) 0.0014(6) 0.0082(6) C17 0.0460(8) 0.0244(7) 0.0322(7) 0.0021(5) -0.0042(6) -0.0013(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 N1 C2 1.3439(16) . ? N1 C1 1.4587(15) . ? N1 H1A 0.880(3) . ? O1 C2 1.2333(15) . ? O2 C7 1.1984(15) . ? O3 C7 1.3476(14) . ? O3 C8 1.4455(14) . ? C1 C7 1.5270(17) . ? C1 C15 1.5561(17) . ? C1 C4 1.5737(16) . ? C2 C3 1.4929(17) . ? C3 C5 1.3190(18) . ? C3 C4 1.5091(16) . ? C4 C6 1.5225(17) . ? C4 H4A 1.0000 . ? C5 H5A 0.9500 . ? C5 H5B 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 C9 1.5102(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.3862(18) . ? C9 C10 1.3918(18) . ? C10 C11 1.384(2) . ? C10 H10A 0.9500 . ? C11 C12 1.385(2) . ? C11 H11A 0.9500 . ? C12 C13 1.382(2) . ? C12 H12A 0.9500 . ? C13 C14 1.3879(19) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C17 1.5292(18) . ? C15 C16 1.5312(18) . ? C15 H15A 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 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 C2 N1 C1 114.78(10) . . ? C2 N1 H1A 122.2(10) . . ? C1 N1 H1A 121.4(9) . . ? C7 O3 C8 116.96(10) . . ? N1 C1 C7 108.93(10) . . ? N1 C1 C15 111.35(10) . . ? C7 C1 C15 110.36(9) . . ? N1 C1 C4 102.13(9) . . ? C7 C1 C4 108.73(9) . . ? C15 C1 C4 114.94(10) . . ? O1 C2 N1 126.11(12) . . ? O1 C2 C3 126.35(11) . . ? N1 C2 C3 107.54(10) . . ? C5 C3 C2 123.29(12) . . ? C5 C3 C4 129.42(12) . . ? C2 C3 C4 107.27(10) . . ? C3 C4 C6 116.60(10) . . ? C3 C4 C1 103.05(9) . . ? C6 C4 C1 117.12(10) . . ? C3 C4 H4A 106.4 . . ? C6 C4 H4A 106.4 . . ? C1 C4 H4A 106.4 . . ? C3 C5 H5A 120.0 . . ? C3 C5 H5B 120.0 . . ? H5A C5 H5B 120.0 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O2 C7 O3 124.51(11) . . ? O2 C7 C1 125.91(11) . . ? O3 C7 C1 109.58(10) . . ? O3 C8 C9 112.57(10) . . ? O3 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? O3 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 118.90(12) . . ? C14 C9 C8 123.20(11) . . ? C10 C9 C8 117.89(11) . . ? C11 C10 C9 120.58(13) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C12 120.05(13) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C13 C12 C11 119.79(13) . . ? C13 C12 H12A 120.1 . . ? C11 C12 H12A 120.1 . . ? C12 C13 C14 120.11(13) . . ? C12 C13 H13A 119.9 . . ? C14 C13 H13A 119.9 . . ? C9 C14 C13 120.56(12) . . ? C9 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C17 C15 C16 109.69(11) . . ? C17 C15 C1 111.34(11) . . ? C16 C15 C1 111.67(10) . . ? C17 C15 H15A 108.0 . . ? C16 C15 H15A 108.0 . . ? C1 C15 H15A 108.0 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 C7 134.03(11) . . . . ? C2 N1 C1 C15 -104.02(12) . . . . ? C2 N1 C1 C4 19.15(13) . . . . ? C1 N1 C2 O1 173.21(12) . . . . ? C1 N1 C2 C3 -7.41(14) . . . . ? O1 C2 C3 C5 -7.5(2) . . . . ? N1 C2 C3 C5 173.09(12) . . . . ? O1 C2 C3 C4 170.90(12) . . . . ? N1 C2 C3 C4 -8.48(13) . . . . ? C5 C3 C4 C6 -32.84(19) . . . . ? C2 C3 C4 C6 148.86(11) . . . . ? C5 C3 C4 C1 -162.58(13) . . . . ? C2 C3 C4 C1 19.12(12) . . . . ? N1 C1 C4 C3 -22.18(11) . . . . ? C7 C1 C4 C3 -137.22(10) . . . . ? C15 C1 C4 C3 98.53(11) . . . . ? N1 C1 C4 C6 -151.60(11) . . . . ? C7 C1 C4 C6 93.36(12) . . . . ? C15 C1 C4 C6 -30.89(15) . . . . ? C8 O3 C7 O2 0.66(17) . . . . ? C8 O3 C7 C1 -179.97(9) . . . . ? N1 C1 C7 O2 -0.36(17) . . . . ? C15 C1 C7 O2 -122.90(13) . . . . ? C4 C1 C7 O2 110.18(13) . . . . ? N1 C1 C7 O3 -179.72(9) . . . . ? C15 C1 C7 O3 57.74(12) . . . . ? C4 C1 C7 O3 -69.18(12) . . . . ? C7 O3 C8 C9 -92.43(13) . . . . ? O3 C8 C9 C14 5.30(18) . . . . ? O3 C8 C9 C10 -173.95(11) . . . . ? C14 C9 C10 C11 0.2(2) . . . . ? C8 C9 C10 C11 179.44(12) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? C10 C11 C12 C13 -0.3(2) . . . . ? C11 C12 C13 C14 0.5(2) . . . . ? C10 C9 C14 C13 0.0(2) . . . . ? C8 C9 C14 C13 -179.21(12) . . . . ? C12 C13 C14 C9 -0.4(2) . . . . ? N1 C1 C15 C17 -72.75(13) . . . . ? C7 C1 C15 C17 48.36(13) . . . . ? C4 C1 C15 C17 171.75(10) . . . . ? N1 C1 C15 C16 50.24(14) . . . . ? C7 C1 C15 C16 171.35(11) . . . . ? C4 C1 C15 C16 -65.26(14) . . . . ? 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 N1 H1A O1 0.880(3) 2.022(4) 2.8960(14) 172.0(14) 2_666 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.302 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.038 # Attachment '- 10102a.cif' data_10102a _database_code_depnum_ccdc_archive 'CCDC 805101' #TrackingRef '- 10102a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 10102a _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 N O3' _chemical_formula_sum 'C23 H25 N O3' _chemical_formula_weight 363.44 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 8.4398(11) _cell_length_b 10.1347(13) _cell_length_c 13.0478(17) _cell_angle_alpha 94.817(2) _cell_angle_beta 107.229(2) _cell_angle_gamma 109.137(2) _cell_volume 986.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4086 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 26.90 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9608 _exptl_absorpt_correction_T_max 0.9724 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details 'Prof. V. Mereddy' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10405 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3997 _reflns_number_gt 2776 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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^)+(0.0430P)^2^+0.2709P] 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 3997 _refine_ls_number_parameters 249 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 N1 N 0.57037(19) 0.14666(16) 0.43381(12) 0.0281(4) Uani 1 1 d D . . H1A H 0.4723(14) 0.0974(16) 0.4454(14) 0.034 Uiso 1 1 d D . . O1 O 0.74086(16) 0.03041(14) 0.52893(11) 0.0364(3) Uani 1 1 d . . . O2 O 0.40132(16) 0.33731(13) 0.42818(10) 0.0342(3) Uani 1 1 d . . . O3 O 0.50183(16) 0.42758(13) 0.29813(10) 0.0330(3) Uani 1 1 d . . . C1 C 0.5724(2) 0.23440(18) 0.35108(14) 0.0246(4) Uani 1 1 d . . . C2 C 0.7193(2) 0.11728(19) 0.47086(14) 0.0286(4) Uani 1 1 d . . . C3 C 0.8536(2) 0.21049(19) 0.42911(14) 0.0266(4) Uani 1 1 d . . . C4 C 0.7796(2) 0.31774(18) 0.38241(14) 0.0251(4) Uani 1 1 d . . . H4A H 0.8142 0.3967 0.4457 0.030 Uiso 1 1 calc R . . C5 C 1.0053(2) 0.1947(2) 0.43562(15) 0.0357(5) Uani 1 1 d . . . H5A H 1.0333 0.1210 0.4682 0.054 Uiso 1 1 calc R . . H5B H 1.0865 0.2570 0.4078 0.054 Uiso 1 1 calc R . . C6 C 0.8477(2) 0.38738(18) 0.29789(14) 0.0246(4) Uani 1 1 d . . . C7 C 0.8634(2) 0.31078(19) 0.21025(14) 0.0284(4) Uani 1 1 d . . . H7A H 0.8307 0.2104 0.2021 0.034 Uiso 1 1 calc R . . C8 C 0.9262(2) 0.3794(2) 0.13480(15) 0.0330(4) Uani 1 1 d . . . H8A H 0.9353 0.3257 0.0750 0.040 Uiso 1 1 calc R . . C9 C 0.9757(2) 0.5250(2) 0.14596(16) 0.0365(5) Uani 1 1 d . . . H9A H 1.0182 0.5718 0.0939 0.044 Uiso 1 1 calc R . . C10 C 0.9630(3) 0.6025(2) 0.23314(17) 0.0389(5) Uani 1 1 d . . . H10A H 0.9981 0.7031 0.2416 0.047 Uiso 1 1 calc R . . C11 C 0.8994(2) 0.53429(19) 0.30821(15) 0.0324(4) Uani 1 1 d . . . H11A H 0.8908 0.5887 0.3679 0.039 Uiso 1 1 calc R . . C12 C 0.4810(2) 0.33756(18) 0.36590(14) 0.0263(4) Uani 1 1 d . . . C13 C 0.4240(3) 0.5367(2) 0.30141(16) 0.0347(5) Uani 1 1 d . . . H13A H 0.4592 0.5872 0.3777 0.042 Uiso 1 1 calc R . . H13B H 0.2920 0.4933 0.2699 0.042 Uiso 1 1 calc R . . C14 C 0.4967(2) 0.63683(19) 0.23432(15) 0.0312(4) Uani 1 1 d . . . C15 C 0.6321(3) 0.7673(2) 0.28441(17) 0.0421(5) Uani 1 1 d . . . H15A H 0.6735 0.7970 0.3618 0.051 Uiso 1 1 calc R . . C16 C 0.7076(3) 0.8552(2) 0.2220(2) 0.0522(6) Uani 1 1 d . . . H16A H 0.8011 0.9448 0.2569 0.063 Uiso 1 1 calc R . . C17 C 0.6482(3) 0.8137(2) 0.1105(2) 0.0528(6) Uani 1 1 d . . . H17A H 0.7012 0.8743 0.0683 0.063 Uiso 1 1 calc R . . C18 C 0.5118(3) 0.6845(2) 0.05914(18) 0.0459(5) Uani 1 1 d . . . H18A H 0.4697 0.6559 -0.0183 0.055 Uiso 1 1 calc R . . C19 C 0.4366(3) 0.5967(2) 0.12153(16) 0.0364(5) Uani 1 1 d . . . H19A H 0.3425 0.5075 0.0863 0.044 Uiso 1 1 calc R . . C20 C 0.4835(2) 0.14020(18) 0.23570(14) 0.0270(4) Uani 1 1 d . . . H20A H 0.5517 0.0790 0.2286 0.032 Uiso 1 1 calc R . . H20B H 0.4933 0.2028 0.1817 0.032 Uiso 1 1 calc R . . C21 C 0.2859(2) 0.0439(2) 0.20535(15) 0.0338(5) Uani 1 1 d . . . H21A H 0.2675 0.0099 0.2722 0.041 Uiso 1 1 calc R . . C22 C 0.1597(3) 0.1222(2) 0.16418(19) 0.0508(6) Uani 1 1 d . . . H22A H 0.1847 0.2021 0.2219 0.076 Uiso 1 1 calc R . . H22B H 0.0358 0.0563 0.1447 0.076 Uiso 1 1 calc R . . H22C H 0.1779 0.1583 0.0995 0.076 Uiso 1 1 calc R . . C23 C 0.2398(3) -0.0854(2) 0.11829(18) 0.0436(5) Uani 1 1 d . . . H23A H 0.3122 -0.1410 0.1475 0.065 Uiso 1 1 calc R . . H23B H 0.2646 -0.0538 0.0538 0.065 Uiso 1 1 calc R . . H23C H 0.1129 -0.1447 0.0975 0.065 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 N1 0.0230(8) 0.0343(9) 0.0320(9) 0.0156(7) 0.0135(7) 0.0110(7) O1 0.0305(7) 0.0443(8) 0.0425(8) 0.0259(7) 0.0155(6) 0.0171(6) O2 0.0327(7) 0.0396(8) 0.0379(8) 0.0105(6) 0.0203(6) 0.0152(6) O3 0.0383(7) 0.0371(7) 0.0378(8) 0.0177(6) 0.0202(6) 0.0230(6) C1 0.0220(9) 0.0289(9) 0.0255(10) 0.0100(8) 0.0114(7) 0.0087(7) C2 0.0260(9) 0.0337(10) 0.0273(10) 0.0092(8) 0.0090(8) 0.0118(8) C3 0.0235(9) 0.0312(10) 0.0240(10) 0.0067(8) 0.0077(7) 0.0087(8) C4 0.0223(9) 0.0258(9) 0.0265(10) 0.0051(7) 0.0085(7) 0.0080(7) C5 0.0271(10) 0.0411(11) 0.0405(12) 0.0151(9) 0.0113(9) 0.0133(9) C6 0.0169(8) 0.0286(10) 0.0277(10) 0.0075(8) 0.0072(7) 0.0078(7) C7 0.0260(9) 0.0252(9) 0.0335(10) 0.0060(8) 0.0115(8) 0.0075(8) C8 0.0317(10) 0.0405(12) 0.0295(11) 0.0085(9) 0.0144(8) 0.0128(9) C9 0.0356(11) 0.0423(12) 0.0383(12) 0.0206(10) 0.0191(9) 0.0142(9) C10 0.0412(11) 0.0277(10) 0.0513(13) 0.0161(10) 0.0210(10) 0.0104(9) C11 0.0317(10) 0.0296(10) 0.0359(11) 0.0054(8) 0.0138(9) 0.0096(8) C12 0.0193(8) 0.0309(10) 0.0255(10) 0.0060(8) 0.0056(8) 0.0069(7) C13 0.0378(11) 0.0383(11) 0.0389(12) 0.0114(9) 0.0163(9) 0.0243(9) C14 0.0322(10) 0.0308(10) 0.0345(11) 0.0079(8) 0.0091(8) 0.0184(8) C15 0.0442(12) 0.0369(12) 0.0417(12) 0.0034(10) 0.0059(10) 0.0195(10) C16 0.0460(13) 0.0299(12) 0.0749(18) 0.0094(12) 0.0170(12) 0.0105(10) C17 0.0545(14) 0.0459(14) 0.0721(18) 0.0308(13) 0.0329(13) 0.0216(12) C18 0.0514(13) 0.0555(14) 0.0395(13) 0.0182(11) 0.0187(11) 0.0260(12) C19 0.0363(11) 0.0343(11) 0.0377(12) 0.0075(9) 0.0101(9) 0.0141(9) C20 0.0250(9) 0.0293(10) 0.0298(10) 0.0094(8) 0.0115(8) 0.0113(8) C21 0.0251(9) 0.0390(11) 0.0312(11) 0.0077(9) 0.0086(8) 0.0051(8) C22 0.0273(10) 0.0537(14) 0.0601(15) -0.0084(11) 0.0046(10) 0.0150(10) C23 0.0349(11) 0.0322(11) 0.0523(13) 0.0059(10) 0.0060(10) 0.0067(9) _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 N1 C2 1.346(2) . ? N1 C1 1.455(2) . ? N1 H1A 0.879(3) . ? O1 C2 1.232(2) . ? O2 C12 1.198(2) . ? O3 C12 1.329(2) . ? O3 C13 1.463(2) . ? C1 C12 1.520(2) . ? C1 C20 1.536(2) . ? C1 C4 1.578(2) . ? C2 C3 1.491(2) . ? C3 C5 1.321(2) . ? C3 C4 1.508(2) . ? C4 C6 1.512(2) . ? C4 H4A 1.0000 . ? C5 H5A 0.9500 . ? C5 H5B 0.9500 . ? C6 C11 1.390(2) . ? C6 C7 1.391(2) . ? C7 C8 1.384(2) . ? C7 H7A 0.9500 . ? C8 C9 1.378(3) . ? C8 H8A 0.9500 . ? C9 C10 1.378(3) . ? C9 H9A 0.9500 . ? C10 C11 1.381(3) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C13 C14 1.494(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.380(3) . ? C14 C19 1.382(3) . ? C15 C16 1.385(3) . ? C15 H15A 0.9500 . ? C16 C17 1.369(3) . ? C16 H16A 0.9500 . ? C17 C18 1.377(3) . ? C17 H17A 0.9500 . ? C18 C19 1.383(3) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C21 1.539(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C23 1.521(3) . ? C21 C22 1.529(3) . ? C21 H21A 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C2 N1 C1 113.89(14) . . ? C2 N1 H1A 120.9(12) . . ? C1 N1 H1A 123.1(12) . . ? C12 O3 C13 117.31(13) . . ? N1 C1 C12 110.09(14) . . ? N1 C1 C20 110.44(14) . . ? C12 C1 C20 111.31(14) . . ? N1 C1 C4 100.74(13) . . ? C12 C1 C4 110.24(13) . . ? C20 C1 C4 113.54(13) . . ? O1 C2 N1 126.39(16) . . ? O1 C2 C3 126.52(16) . . ? N1 C2 C3 107.09(14) . . ? C5 C3 C2 123.26(17) . . ? C5 C3 C4 130.12(16) . . ? C2 C3 C4 106.62(14) . . ? C3 C4 C6 117.62(14) . . ? C3 C4 C1 101.55(13) . . ? C6 C4 C1 118.62(13) . . ? C3 C4 H4A 106.0 . . ? C6 C4 H4A 106.0 . . ? C1 C4 H4A 106.0 . . ? C3 C5 H5A 120.0 . . ? C3 C5 H5B 120.0 . . ? H5A C5 H5B 120.0 . . ? C11 C6 C7 118.13(16) . . ? C11 C6 C4 119.08(16) . . ? C7 C6 C4 122.78(15) . . ? C8 C7 C6 120.64(17) . . ? C8 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C9 C8 C7 120.40(18) . . ? C9 C8 H8A 119.8 . . ? C7 C8 H8A 119.8 . . ? C8 C9 C10 119.58(17) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C9 C10 C11 120.18(18) . . ? C9 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C10 C11 C6 121.06(18) . . ? C10 C11 H11A 119.5 . . ? C6 C11 H11A 119.5 . . ? O2 C12 O3 125.23(16) . . ? O2 C12 C1 125.45(16) . . ? O3 C12 C1 109.32(14) . . ? O3 C13 C14 105.32(14) . . ? O3 C13 H13A 110.7 . . ? C14 C13 H13A 110.7 . . ? O3 C13 H13B 110.7 . . ? C14 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C19 119.02(18) . . ? C15 C14 C13 120.43(18) . . ? C19 C14 C13 120.44(17) . . ? C14 C15 C16 120.1(2) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C17 C16 C15 120.4(2) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 120.3(2) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C17 C18 C19 119.3(2) . . ? C17 C18 H18A 120.3 . . ? C19 C18 H18A 120.3 . . ? C14 C19 C18 120.94(19) . . ? C14 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? C1 C20 C21 115.82(14) . . ? C1 C20 H20A 108.3 . . ? C21 C20 H20A 108.3 . . ? C1 C20 H20B 108.3 . . ? C21 C20 H20B 108.3 . . ? H20A C20 H20B 107.4 . . ? C23 C21 C22 109.48(16) . . ? C23 C21 C20 109.80(15) . . ? C22 C21 C20 112.47(15) . . ? C23 C21 H21A 108.3 . . ? C22 C21 H21A 108.3 . . ? C20 C21 H21A 108.3 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 C12 -143.31(15) . . . . ? C2 N1 C1 C20 93.38(17) . . . . ? C2 N1 C1 C4 -26.92(19) . . . . ? C1 N1 C2 O1 -169.37(17) . . . . ? C1 N1 C2 C3 11.1(2) . . . . ? O1 C2 C3 C5 11.2(3) . . . . ? N1 C2 C3 C5 -169.30(18) . . . . ? O1 C2 C3 C4 -168.63(18) . . . . ? N1 C2 C3 C4 10.92(19) . . . . ? C5 C3 C4 C6 23.2(3) . . . . ? C2 C3 C4 C6 -157.07(15) . . . . ? C5 C3 C4 C1 154.38(19) . . . . ? C2 C3 C4 C1 -25.86(17) . . . . ? N1 C1 C4 C3 30.55(16) . . . . ? C12 C1 C4 C3 146.83(14) . . . . ? C20 C1 C4 C3 -87.50(16) . . . . ? N1 C1 C4 C6 161.14(15) . . . . ? C12 C1 C4 C6 -82.59(18) . . . . ? C20 C1 C4 C6 43.1(2) . . . . ? C3 C4 C6 C11 -133.12(17) . . . . ? C1 C4 C6 C11 103.99(19) . . . . ? C3 C4 C6 C7 46.0(2) . . . . ? C1 C4 C6 C7 -76.9(2) . . . . ? C11 C6 C7 C8 -1.0(2) . . . . ? C4 C6 C7 C8 179.88(15) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C7 C8 C9 C10 0.3(3) . . . . ? C8 C9 C10 C11 -0.7(3) . . . . ? C9 C10 C11 C6 0.2(3) . . . . ? C7 C6 C11 C10 0.6(3) . . . . ? C4 C6 C11 C10 179.77(16) . . . . ? C13 O3 C12 O2 1.2(2) . . . . ? C13 O3 C12 C1 -179.36(14) . . . . ? N1 C1 C12 O2 -7.6(2) . . . . ? C20 C1 C12 O2 115.18(18) . . . . ? C4 C1 C12 O2 -117.90(18) . . . . ? N1 C1 C12 O3 172.92(13) . . . . ? C20 C1 C12 O3 -64.27(17) . . . . ? C4 C1 C12 O3 62.65(17) . . . . ? C12 O3 C13 C14 169.55(14) . . . . ? O3 C13 C14 C15 -103.35(19) . . . . ? O3 C13 C14 C19 72.8(2) . . . . ? C19 C14 C15 C16 -0.9(3) . . . . ? C13 C14 C15 C16 175.32(17) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C16 C17 C18 C19 -0.6(3) . . . . ? C15 C14 C19 C18 0.8(3) . . . . ? C13 C14 C19 C18 -175.43(17) . . . . ? C17 C18 C19 C14 -0.1(3) . . . . ? N1 C1 C20 C21 61.27(19) . . . . ? C12 C1 C20 C21 -61.33(19) . . . . ? C4 C1 C20 C21 173.57(14) . . . . ? C1 C20 C21 C23 -154.19(15) . . . . ? C1 C20 C21 C22 83.6(2) . . . . ? 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 N1 H1A O1 0.879(3) 1.982(4) 2.8581(19) 174.2(17) 2_656 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.167 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.039