# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/331 data_bminal _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H25 N O3' _chemical_formula_weight 291.38 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.0668(10) _cell_length_b 11.952(3) _cell_length_c 23.096(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1674.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method ? _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.628 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method 'omega-theta' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1488 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.2125 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 60.09 _reflns_number_total 1447 _reflns_number_observed 552 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 6 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1101P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _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 0.71(184) _refine_ls_number_reflns 1441 _refine_ls_number_parameters 190 _refine_ls_number_restraints 185 _refine_ls_R_factor_all 0.2362 _refine_ls_R_factor_obs 0.0997 _refine_ls_wR_factor_all 0.2847 _refine_ls_wR_factor_obs 0.2053 _refine_ls_goodness_of_fit_all 1.012 _refine_ls_goodness_of_fit_obs 1.335 _refine_ls_restrained_S_all 0.966 _refine_ls_restrained_S_obs 1.110 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.5309(25) 0.1301(11) 0.2360(6) 0.049(4) Uani 1 d U . H1A H 0.6758(25) 0.0956(11) 0.2417(6) 0.058 Uiso 1 calc R . H1B H 0.4192(25) 0.0805(11) 0.2527(6) 0.058 Uiso 1 calc R . C2 C 0.5241(23) 0.2390(12) 0.2648(6) 0.053(4) Uani 1 d U . H2A H 0.6418(23) 0.2865(12) 0.2493(6) 0.064 Uiso 1 calc R . H2B H 0.5517(23) 0.2287(12) 0.3063(6) 0.064 Uiso 1 calc R . C3 C 0.2986(23) 0.2989(11) 0.2565(6) 0.043(3) Uani 1 d U . H3 H 0.3183(23) 0.3794(11) 0.2653(6) 0.052 Uiso 1 calc R . C3M C 0.1270(22) 0.2506(12) 0.2988(5) 0.048(4) Uani 1 d U . H3M1 H -0.0128(22) 0.2885(12) 0.2933(5) 0.072 Uiso 1 calc R . H3M2 H 0.1771(22) 0.2617(12) 0.3383(5) 0.072 Uiso 1 calc R . H3M3 H 0.1087(22) 0.1713(12) 0.2915(5) 0.072 Uiso 1 calc R . C4 C 0.2746(24) 0.1881(10) 0.1606(6) 0.044(3) Uani 1 d U . H4 H 0.2737(24) 0.2100(10) 0.1193(6) 0.052 Uiso 1 calc R . C5 C 0.0984(22) 0.0962(11) 0.1706(6) 0.046(3) Uani 1 d U . H5A H 0.1235(22) 0.0607(11) 0.2083(6) 0.055 Uiso 1 calc R . H5B H -0.0483(22) 0.1305(11) 0.1712(6) 0.055 Uiso 1 calc R . C6 C 0.1063(23) 0.0090(10) 0.1241(5) 0.030(3) Uani 1 d U . C7 C 0.2836(24) -0.0668(11) 0.1193(6) 0.044(3) Uani 1 d U . H7 H 0.4046(24) -0.0612(11) 0.1446(6) 0.053 Uiso 1 calc R . C8 C 0.2790(27) -0.1475(12) 0.0784(5) 0.050(4) Uani 1 d U . H8 H 0.4007(27) -0.1959(12) 0.0760(5) 0.060 Uiso 1 calc R . C9 C 0.1084(29) -0.1639(13) 0.0398(6) 0.062(4) Uani 1 d U . H9 H 0.1120(29) -0.2206(13) 0.0116(6) 0.075 Uiso 1 calc R . C10 C -0.0736(28) -0.0894(13) 0.0455(6) 0.057(4) Uani 1 d U . H10 H -0.1969(28) -0.0972(13) 0.0212(6) 0.068 Uiso 1 calc R . C11 C -0.0687(28) -0.0069(13) 0.0861(6) 0.057(4) Uani 1 d U . H11 H -0.1900(28) 0.0418(13) 0.0886(6) 0.068 Uiso 1 calc R . N12 N 0.2292(18) 0.2883(9) 0.1966(5) 0.040(2) Uani 1 d U . O13 O 0.4898(14) 0.1447(7) 0.1753(4) 0.044(2) Uani 1 d U . C1B C 0.0945(22) 0.3704(11) 0.1732(6) 0.037(3) Uani 1 d U . O1B O 0.0403(16) 0.4524(7) 0.2023(4) 0.052(3) Uani 1 d U . O2B O 0.0321(15) 0.3444(7) 0.1207(4) 0.046(2) Uani 1 d U . C3B C -0.1036(25) 0.4205(13) 0.0864(6) 0.049(3) Uani 1 d U . C4B C -0.3328(23) 0.4384(16) 0.1161(7) 0.079(6) Uani 1 d U . H4B1 H -0.4051(23) 0.3666(16) 0.1211(7) 0.119 Uiso 1 calc R . H4B2 H -0.4235(23) 0.4863(16) 0.0920(7) 0.119 Uiso 1 calc R . H4B3 H -0.3118(23) 0.4732(16) 0.1537(7) 0.119 Uiso 1 calc R . C5B C -0.1235(33) 0.3616(16) 0.0286(6) 0.104(7) Uani 1 d U . H5B1 H -0.1956(33) 0.2899(16) 0.0340(6) 0.156 Uiso 1 calc R . H5B2 H 0.0223(33) 0.3498(16) 0.0125(6) 0.156 Uiso 1 calc R . H5B3 H -0.2098(33) 0.4072(16) 0.0023(6) 0.156 Uiso 1 calc R . C6B C 0.0063(28) 0.5302(12) 0.0789(7) 0.084(6) Uani 1 d U . H6B1 H 0.0182(28) 0.5672(12) 0.1161(7) 0.126 Uiso 1 calc R . H6B2 H -0.0798(28) 0.5763(12) 0.0528(7) 0.126 Uiso 1 calc R . H6B3 H 0.1524(28) 0.5189(12) 0.0629(7) 0.126 Uiso 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 0.030(8) 0.050(8) 0.066(7) 0.014(7) 0.009(7) 0.012(7) C2 0.028(7) 0.060(8) 0.071(8) 0.008(7) -0.006(7) -0.002(8) C3 0.040(7) 0.034(8) 0.056(7) 0.000(6) -0.015(6) 0.002(6) C3M 0.040(8) 0.066(10) 0.037(6) -0.023(8) -0.003(7) 0.015(8) C4 0.039(7) 0.030(6) 0.062(8) -0.003(6) -0.006(7) -0.001(5) C5 0.022(6) 0.043(7) 0.073(9) -0.009(6) 0.008(8) -0.004(6) C6 0.038(7) 0.019(6) 0.034(6) 0.009(5) 0.003(6) -0.002(5) C7 0.035(7) 0.042(8) 0.055(8) -0.007(6) -0.011(7) 0.008(6) C8 0.057(9) 0.057(9) 0.037(8) -0.013(7) 0.016(7) 0.021(8) C9 0.076(10) 0.059(9) 0.052(9) -0.018(8) 0.005(8) -0.014(8) C10 0.066(9) 0.065(10) 0.040(8) 0.003(7) -0.026(8) -0.011(8) C11 0.050(9) 0.064(9) 0.056(9) -0.002(7) -0.016(7) 0.015(8) N12 0.035(6) 0.035(5) 0.048(5) 0.002(5) -0.003(5) -0.001(5) O13 0.019(4) 0.041(5) 0.071(5) 0.006(5) 0.004(5) -0.002(4) C1B 0.028(7) 0.033(7) 0.050(7) -0.005(6) -0.009(6) -0.001(6) O1B 0.056(7) 0.040(5) 0.059(6) -0.009(5) -0.008(6) 0.008(5) O2B 0.042(5) 0.041(5) 0.055(5) 0.004(4) -0.016(5) 0.008(5) C3B 0.032(7) 0.062(8) 0.053(8) 0.013(7) -0.002(7) 0.011(7) C4B 0.030(7) 0.124(15) 0.084(12) 0.037(12) 0.013(8) 0.018(8) C5B 0.113(16) 0.132(14) 0.067(9) -0.019(10) -0.041(10) 0.071(14) C6B 0.046(9) 0.080(9) 0.127(14) 0.061(10) -0.019(12) -0.005(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 C1 O13 1.434(14) . ? C1 C2 1.46(2) . ? C2 C3 1.56(2) . ? C3 N12 1.452(15) . ? C3 C3M 1.54(2) . ? C4 O13 1.45(2) . ? C4 N12 1.483(15) . ? C4 C5 1.55(2) . ? C5 C6 1.50(2) . ? C6 C11 1.39(2) . ? C6 C7 1.41(2) . ? C7 C8 1.35(2) . ? C8 C9 1.38(2) . ? C9 C10 1.42(2) . ? C10 C11 1.36(2) . ? N12 C1B 1.39(2) . ? C1B O1B 1.233(14) . ? C1B O2B 1.307(14) . ? O2B C3B 1.46(2) . ? C3B C6B 1.48(2) . ? C3B C5B 1.51(2) . ? C3B C4B 1.57(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O13 C1 C2 109.4(11) . . ? C1 C2 C3 112.2(12) . . ? N12 C3 C3M 112.0(11) . . ? N12 C3 C2 109.4(12) . . ? C3M C3 C2 110.1(11) . . ? O13 C4 N12 109.0(11) . . ? O13 C4 C5 109.4(10) . . ? N12 C4 C5 111.2(11) . . ? C6 C5 C4 111.4(11) . . ? C11 C6 C7 116.4(12) . . ? C11 C6 C5 121.6(13) . . ? C7 C6 C5 121.8(13) . . ? C8 C7 C6 119.8(14) . . ? C7 C8 C9 124.7(15) . . ? C8 C9 C10 115.7(14) . . ? C11 C10 C9 119.9(15) . . ? C10 C11 C6 123.4(15) . . ? C1B N12 C3 118.7(11) . . ? C1B N12 C4 117.5(10) . . ? C3 N12 C4 123.5(11) . . ? C1 O13 C4 115.5(11) . . ? O1B C1B O2B 128.1(13) . . ? O1B C1B N12 120.5(12) . . ? O2B C1B N12 111.4(12) . . ? C1B O2B C3B 121.2(11) . . ? O2B C3B C6B 111.2(12) . . ? O2B C3B C5B 103.5(12) . . ? C6B C3B C5B 110.1(15) . . ? O2B C3B C4B 110.4(11) . . ? C6B C3B C4B 109.3(14) . . ? C5B C3B C4B 112.3(14) . . ? _refine_diff_density_max 0.257 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.080