data_11jo0022s _audit_creation_date 2011-11-17 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H17 N O3' _chemical_formula_sum 'C13 H17 N O3' _chemical_formula_weight 235.28 _chemical_melting_point ? _chemical_oxdiff_formula 'C13 H17 N O3' 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' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 12.3286(3) _cell_length_b 10.3522(2) _cell_length_c 10.2050(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.066(2) _cell_angle_gamma 90.00 _cell_volume 1295.16(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9276 _cell_measurement_temperature 250.01(11) _cell_measurement_theta_max 28.6041 _cell_measurement_theta_min 1.6577 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.512 _exptl_crystal_size_mid 0.4293 _exptl_crystal_size_min 0.3241 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_unetI/netI 0.0227 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 20601 _diffrn_reflns_theta_full 28.67 _diffrn_reflns_theta_max 28.67 _diffrn_reflns_theta_min 1.66 _diffrn_ambient_temperature 250.01(11) _diffrn_detector_area_resol_mean 10.3590 _diffrn_measured_fraction_theta_full 0.945 _diffrn_measured_fraction_theta_max 0.945 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -70.00 111.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.8337 -19.0000 0.0000 181 #__ type_ start__ end____ width___ exp.time_ 2 omega 35.00 68.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -19.6931 178.0000 150.0000 33 #__ type_ start__ end____ width___ exp.time_ 3 omega -75.00 113.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.8337 19.0000 150.0000 188 #__ type_ start__ end____ width___ exp.time_ 4 omega 34.00 118.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.8337 -178.0000 120.0000 84 #__ type_ start__ end____ width___ exp.time_ 5 omega -20.00 31.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -19.6931 -99.0000 -90.0000 51 #__ type_ start__ end____ width___ exp.time_ 6 omega -20.00 31.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -19.6931 -99.0000 -150.0000 51 #__ type_ start__ end____ width___ exp.time_ 7 omega 35.00 81.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -19.6931 178.0000 -30.0000 46 #__ type_ start__ end____ width___ exp.time_ 8 omega -61.00 72.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -19.6931 57.0000 -90.0000 133 #__ type_ start__ end____ width___ exp.time_ 9 omega -28.00 39.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.8337 38.0000 -90.0000 67 #__ type_ start__ end____ width___ exp.time_ 10 omega 34.00 118.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.8337 -178.0000 -90.0000 84 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_measurement_method '\w and \f scans' _diffrn_orient_matrix_UB_11 0.0084886000 _diffrn_orient_matrix_UB_12 0.0042135000 _diffrn_orient_matrix_UB_13 -0.0675378000 _diffrn_orient_matrix_UB_21 -0.0495866000 _diffrn_orient_matrix_UB_22 0.0346630000 _diffrn_orient_matrix_UB_23 -0.0129761000 _diffrn_orient_matrix_UB_31 0.0285076000 _diffrn_orient_matrix_UB_32 0.0590115000 _diffrn_orient_matrix_UB_33 0.0123638000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_source ' 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2453 _reflns_number_total 3161 _reflns_odcompleteness_completeness 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.158 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.028 _refine_ls_extinction_coef 0.056(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 159 _refine_ls_number_reflns 3161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0414 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.1986P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1017 _refine_ls_wR_factor_ref 0.1108 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.34410(8) 0.20581(9) 0.23111(8) 0.0414(2) Uani 1 1 d . . . H1 H 0.3245 0.2183 0.1487 0.050 Uiso 1 1 calc R . . O2 O 0.31494(7) 0.26987(10) 0.43765(7) 0.0568(3) Uani 1 1 d . . . C3 C 0.29356(9) 0.27330(11) 0.31734(11) 0.0429(3) Uani 1 1 d . . . C4 C 0.09800(10) 0.36117(11) 0.31507(11) 0.0453(3) Uani 1 1 d . . . C5 C 0.20230(11) 0.36234(12) 0.25661(11) 0.0487(3) Uani 1 1 d . . . C6 C 0.43186(9) 0.11042(10) 0.26721(10) 0.0398(3) Uani 1 1 d . . . C7 C 0.07271(10) 0.26813(12) 0.40515(12) 0.0495(3) Uani 1 1 d . . . H7 H 0.1237 0.2045 0.4314 0.059 Uiso 1 1 calc R . . O8 O 0.21991(9) 0.43208(11) 0.16515(10) 0.0759(3) Uani 1 1 d . . . O9 O -0.20075(8) 0.37528(11) 0.46652(12) 0.0772(3) Uani 1 1 d . . . C10 C -0.10194(10) 0.36411(13) 0.41979(14) 0.0556(3) Uani 1 1 d . . . C11 C 0.38910(11) 0.00443(12) 0.35202(12) 0.0524(3) Uani 1 1 d . . . H11A H 0.3670 0.0418 0.4311 0.079 Uiso 1 1 calc R . . H11B H 0.4457 -0.0579 0.3745 0.079 Uiso 1 1 calc R . . H11C H 0.3278 -0.0373 0.3038 0.079 Uiso 1 1 calc R . . C12 C -0.02670(11) 0.26804(13) 0.45665(14) 0.0544(3) Uani 1 1 d . . . H12 H -0.0428 0.2040 0.5155 0.065 Uiso 1 1 calc R . . C13 C 0.46174(12) 0.05163(13) 0.13944(12) 0.0536(3) Uani 1 1 d . . . H13A H 0.3984 0.0119 0.0934 0.080 Uiso 1 1 calc R . . H13B H 0.5176 -0.0123 0.1588 0.080 Uiso 1 1 calc R . . H13C H 0.4881 0.1181 0.0854 0.080 Uiso 1 1 calc R . . C14 C 0.53126(10) 0.17657(12) 0.33885(12) 0.0513(3) Uani 1 1 d . . . H14A H 0.5553 0.2444 0.2846 0.077 Uiso 1 1 calc R . . H14B H 0.5888 0.1146 0.3570 0.077 Uiso 1 1 calc R . . H14C H 0.5124 0.2125 0.4202 0.077 Uiso 1 1 calc R . . C15 C -0.07809(11) 0.45800(13) 0.32987(15) 0.0605(4) Uani 1 1 d . . . H15 H -0.1287 0.5224 0.3050 0.073 Uiso 1 1 calc R . . C16 C 0.02002(11) 0.45595(12) 0.27774(13) 0.0543(3) Uani 1 1 d . . . H16 H 0.0349 0.5185 0.2167 0.065 Uiso 1 1 calc R . . C2 C -0.22717(14) 0.2853(2) 0.5637(2) 0.0939(6) Uani 1 1 d . . . H2A H -0.2270 0.1995 0.5282 0.141 Uiso 1 1 calc R . . H2B H -0.2982 0.3047 0.5890 0.141 Uiso 1 1 calc R . . H2C H -0.1741 0.2912 0.6394 0.141 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 0.0540(6) 0.0436(5) 0.0262(4) 0.0013(4) 0.0032(4) 0.0068(4) O2 0.0579(5) 0.0807(6) 0.0310(4) -0.0125(4) 0.0003(4) 0.0096(4) C3 0.0470(6) 0.0463(6) 0.0350(6) -0.0045(4) 0.0029(4) 0.0004(5) C4 0.0501(7) 0.0406(6) 0.0439(6) -0.0053(5) -0.0010(5) 0.0031(5) C5 0.0591(7) 0.0454(6) 0.0412(6) -0.0023(5) 0.0033(5) 0.0055(5) C6 0.0523(7) 0.0364(5) 0.0308(5) 0.0030(4) 0.0046(4) 0.0029(5) C7 0.0518(7) 0.0436(6) 0.0517(7) -0.0001(5) -0.0010(5) 0.0059(5) O8 0.0819(7) 0.0783(7) 0.0710(7) 0.0278(6) 0.0246(5) 0.0225(6) O9 0.0461(6) 0.0861(8) 0.1005(8) 0.0111(6) 0.0127(5) 0.0051(5) C10 0.0433(7) 0.0569(8) 0.0652(8) -0.0040(6) -0.0004(6) -0.0019(6) C11 0.0642(8) 0.0469(7) 0.0460(7) 0.0099(5) 0.0053(6) -0.0035(6) C12 0.0527(7) 0.0513(7) 0.0583(8) 0.0042(6) 0.0019(6) -0.0015(6) C13 0.0723(9) 0.0498(7) 0.0398(6) 0.0000(5) 0.0112(6) 0.0141(6) C14 0.0532(7) 0.0463(7) 0.0539(7) 0.0025(5) 0.0026(6) -0.0001(5) C15 0.0496(8) 0.0531(8) 0.0765(9) 0.0049(7) -0.0038(6) 0.0097(6) C16 0.0558(8) 0.0462(7) 0.0592(8) 0.0066(6) -0.0016(6) 0.0048(6) C2 0.0585(10) 0.1216(16) 0.1046(14) 0.0235(12) 0.0225(9) -0.0052(10) _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 H1 0.8600 . ? N1 C3 1.3291(14) . ? N1 C6 1.4823(14) . ? O2 C3 1.2288(13) . ? C3 C5 1.5337(17) . ? C4 C5 1.4736(17) . ? C4 C7 1.3895(17) . ? C4 C16 1.3981(16) . ? C5 O8 1.2175(14) . ? C6 C11 1.5256(15) . ? C6 C13 1.5191(15) . ? C6 C14 1.5218(16) . ? C7 H7 0.9300 . ? C7 C12 1.3836(18) . ? O9 C10 1.3592(16) . ? O9 C2 1.423(2) . ? C10 C12 1.3846(18) . ? C10 C15 1.3894(19) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15 0.9300 . ? C15 C16 1.3720(19) . ? C16 H16 0.9300 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? 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 C3 N1 H1 117.7 . . ? C3 N1 C6 124.51(9) . . ? C6 N1 H1 117.7 . . ? N1 C3 C5 115.06(9) . . ? O2 C3 N1 125.47(11) . . ? O2 C3 C5 119.46(10) . . ? C7 C4 C5 122.68(11) . . ? C7 C4 C16 118.09(12) . . ? C16 C4 C5 119.23(11) . . ? C4 C5 C3 117.76(10) . . ? O8 C5 C3 118.91(11) . . ? O8 C5 C4 123.30(11) . . ? N1 C6 C11 109.46(9) . . ? N1 C6 C13 106.88(9) . . ? N1 C6 C14 110.43(9) . . ? C13 C6 C11 109.18(10) . . ? C13 C6 C14 109.67(10) . . ? C14 C6 C11 111.11(9) . . ? C4 C7 H7 119.3 . . ? C12 C7 C4 121.43(11) . . ? C12 C7 H7 119.3 . . ? C10 O9 C2 117.93(12) . . ? O9 C10 C12 124.43(13) . . ? O9 C10 C15 115.61(12) . . ? C12 C10 C15 119.96(12) . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C12 C10 119.43(12) . . ? C7 C12 H12 120.3 . . ? C10 C12 H12 120.3 . . ? C6 C13 H13A 109.5 . . ? C6 C13 H13B 109.5 . . ? C6 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 C14 H14A 109.5 . . ? C6 C14 H14B 109.5 . . ? C6 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C15 H15 119.9 . . ? C16 C15 C10 120.13(12) . . ? C16 C15 H15 119.9 . . ? C4 C16 H16 119.5 . . ? C15 C16 C4 120.95(12) . . ? C15 C16 H16 119.5 . . ? O9 C2 H2A 109.5 . . ? O9 C2 H2B 109.5 . . ? O9 C2 H2C 109.5 . . ? H2A C2 H2B 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 3 13 -7 0.1408 3.0000 13.0000 -7.0000 0.5530 0.3927 0.7661 -6 -13 3 0.2245 -6.0000 -13.0000 3.0000 -0.3083 -0.1920 -0.9011 6 1 13 0.1466 6.0000 1.0000 13.0000 -0.8228 -0.4315 0.3908 -7 -3 -12 0.1546 -7.0000 -3.0000 -12.0000 0.7384 0.3988 -0.5250 -16 6 1 0.1700 -16.0000 6.0000 1.0000 -0.1781 0.9884 -0.0897 17 -3 -1 0.1825 17.0000 -3.0000 -1.0000 0.1992 -0.9340 0.2952 12 -10 -2 0.1876 12.0000 -10.0000 -2.0000 0.1948 -0.9157 -0.2728