data_091130_hongd_3ome_mo _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O3' _chemical_formula_sum 'C18 H17 N O3' _chemical_formula_weight 295.33 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' 'O' 'O' 0.0106 0.0060 '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' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 21/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 6.7647(3) _cell_length_b 17.5609(8) _cell_length_c 13.1322(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.811(4) _cell_angle_gamma 90.00 _cell_volume 1559.87(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2830 _cell_measurement_theta_min 3.2208 _cell_measurement_theta_max 28.4240 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET) (compiled Nov 17 2009,16:58:22) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6696 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2610 _reflns_number_gt 1667 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _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^)+(0.0557P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2610 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0913 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _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 -0.04724(16) -0.23712(6) 1.00548(9) 0.0653(4) Uani 1 1 d . . . O2 O 0.15647(17) 0.05084(6) 0.94525(11) 0.0825(5) Uani 1 1 d . . . O3 O 0.44444(14) 0.05784(5) 0.86738(8) 0.0567(3) Uani 1 1 d . . . N1 N 0.16668(16) -0.10744(6) 0.93324(9) 0.0463(3) Uani 1 1 d . . . H1 H 0.0727 -0.0916 0.9713 0.056 Uiso 1 1 calc R . . C1 C -0.1572(3) -0.30297(9) 1.03383(17) 0.0834(6) Uani 1 1 d . . . H1A H -0.2098 -0.3272 0.9738 0.125 Uiso 1 1 calc R . . H1B H -0.2637 -0.2882 1.0771 0.125 Uiso 1 1 calc R . . H1C H -0.0719 -0.3378 1.0697 0.125 Uiso 1 1 calc R . . C2 C 0.1120(2) -0.24837(8) 0.94455(12) 0.0500(4) Uani 1 1 d . . . C3 C 0.1878(2) -0.31645(9) 0.91356(13) 0.0603(5) Uani 1 1 d . . . H3 H 0.1307 -0.3616 0.9358 0.072 Uiso 1 1 calc R . . C4 C 0.3511(2) -0.31935(9) 0.84829(14) 0.0657(5) Uani 1 1 d . . . H4 H 0.3986 -0.3666 0.8280 0.079 Uiso 1 1 calc R . . C5 C 0.4419(2) -0.25528(9) 0.81386(13) 0.0568(4) Uani 1 1 d . . . H5 H 0.5480 -0.2585 0.7698 0.068 Uiso 1 1 calc R . . C6 C 0.37099(19) -0.18388(8) 0.84676(11) 0.0453(4) Uani 1 1 d . . . C7 C 0.20737(19) -0.18166(8) 0.91174(11) 0.0436(4) Uani 1 1 d . . . C8 C 0.30093(19) -0.06184(8) 0.88395(11) 0.0437(4) Uani 1 1 d . . . C9 C 0.42848(19) -0.10654(8) 0.82874(11) 0.0431(4) Uani 1 1 d . . . C10 C 0.5901(2) -0.08319(8) 0.76022(11) 0.0443(4) Uani 1 1 d . . . C11 C 0.7751(2) -0.11712(9) 0.76946(12) 0.0542(4) Uani 1 1 d . . . H11 H 0.7980 -0.1528 0.8206 0.065 Uiso 1 1 calc R . . C12 C 0.9252(2) -0.09871(11) 0.70391(14) 0.0657(5) Uani 1 1 d . . . H12 H 1.0483 -0.1218 0.7113 0.079 Uiso 1 1 calc R . . C13 C 0.8933(3) -0.04639(11) 0.62790(14) 0.0724(6) Uani 1 1 d . . . H13 H 0.9947 -0.0339 0.5838 0.087 Uiso 1 1 calc R . . C14 C 0.7114(3) -0.01240(10) 0.61695(13) 0.0683(5) Uani 1 1 d . . . H14 H 0.6897 0.0230 0.5653 0.082 Uiso 1 1 calc R . . C15 C 0.5608(2) -0.03066(9) 0.68236(12) 0.0557(4) Uani 1 1 d . . . H15 H 0.4379 -0.0075 0.6742 0.067 Uiso 1 1 calc R . . C16 C 0.2896(2) 0.02058(8) 0.90193(11) 0.0483(4) Uani 1 1 d . . . C17 C 0.4474(2) 0.13941(8) 0.88298(13) 0.0574(4) Uani 1 1 d . . . H17B H 0.4568 0.1510 0.9551 0.069 Uiso 1 1 calc R . . H17A H 0.3274 0.1622 0.8556 0.069 Uiso 1 1 calc R . . C18 C 0.6244(3) 0.16981(10) 0.82879(14) 0.0794(6) Uani 1 1 d . . . H18A H 0.6085 0.1614 0.7569 0.119 Uiso 1 1 calc R . . H18C H 0.7411 0.1440 0.8530 0.119 Uiso 1 1 calc R . . H18B H 0.6369 0.2234 0.8418 0.119 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 0.0701(7) 0.0425(6) 0.0839(9) 0.0029(6) 0.0247(7) -0.0107(5) O2 0.0767(8) 0.0462(7) 0.1261(12) -0.0072(7) 0.0573(8) -0.0018(6) O3 0.0543(6) 0.0423(7) 0.0739(8) -0.0059(5) 0.0200(6) -0.0097(5) N1 0.0450(7) 0.0387(7) 0.0554(8) -0.0006(6) 0.0125(6) -0.0007(6) C1 0.0976(14) 0.0519(11) 0.1015(16) 0.0079(11) 0.0343(12) -0.0178(10) C2 0.0528(9) 0.0414(9) 0.0557(10) 0.0027(8) 0.0009(8) -0.0017(7) C3 0.0703(10) 0.0378(9) 0.0726(12) 0.0027(9) 0.0004(9) -0.0015(8) C4 0.0735(11) 0.0419(10) 0.0816(13) -0.0066(9) 0.0017(10) 0.0106(9) C5 0.0562(9) 0.0499(10) 0.0646(11) -0.0038(9) 0.0054(8) 0.0097(8) C6 0.0447(8) 0.0425(9) 0.0487(9) -0.0011(7) -0.0012(7) 0.0040(7) C7 0.0456(8) 0.0381(9) 0.0470(9) -0.0014(7) -0.0017(7) 0.0007(7) C8 0.0400(8) 0.0403(9) 0.0511(9) 0.0023(7) 0.0071(7) -0.0007(6) C9 0.0388(7) 0.0444(9) 0.0461(9) 0.0013(7) 0.0012(7) 0.0023(7) C10 0.0455(8) 0.0438(9) 0.0435(9) -0.0032(7) 0.0034(7) 0.0010(7) C11 0.0452(8) 0.0633(10) 0.0543(10) 0.0056(8) 0.0044(8) 0.0054(7) C12 0.0478(9) 0.0829(13) 0.0666(11) 0.0016(11) 0.0108(9) 0.0070(8) C13 0.0650(11) 0.0873(14) 0.0654(13) 0.0045(11) 0.0247(10) -0.0056(10) C14 0.0826(13) 0.0655(12) 0.0573(11) 0.0140(9) 0.0176(10) 0.0032(9) C15 0.0581(9) 0.0520(10) 0.0571(10) 0.0033(8) 0.0059(8) 0.0094(8) C16 0.0475(8) 0.0427(9) 0.0550(10) 0.0008(8) 0.0134(8) -0.0019(7) C17 0.0691(10) 0.0399(10) 0.0633(11) -0.0009(8) 0.0045(9) -0.0121(7) C18 0.0930(13) 0.0722(12) 0.0730(13) 0.0087(10) 0.0072(10) -0.0370(11) _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 C2 1.3651(17) . ? O1 C1 1.4271(18) . ? O2 C16 1.1966(16) . ? O3 C16 1.3207(15) . ? O3 C17 1.4471(17) . ? N1 C7 1.3626(17) . ? N1 C8 1.3789(16) . ? N1 H1 0.8600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.365(2) . ? C2 C7 1.408(2) . ? C3 C4 1.409(2) . ? C3 H3 0.9300 . ? C4 C5 1.362(2) . ? C4 H4 0.9300 . ? C5 C6 1.412(2) . ? C5 H5 0.9300 . ? C6 C7 1.4076(18) . ? C6 C9 1.4334(19) . ? C8 C9 1.3799(18) . ? C8 C16 1.469(2) . ? C9 C10 1.4833(18) . ? C10 C15 1.389(2) . ? C10 C11 1.390(2) . ? C11 C12 1.379(2) . ? C11 H11 0.9300 . ? C12 C13 1.371(2) . ? C12 H12 0.9300 . ? C13 C14 1.374(2) . ? C13 H13 0.9300 . ? C14 C15 1.380(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.4997(19) . ? C17 H17B 0.9700 . ? C17 H17A 0.9700 . ? C18 H18A 0.9600 . ? C18 H18C 0.9600 . ? C18 H18B 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 C2 O1 C1 117.00(12) . . ? C16 O3 C17 116.83(10) . . ? C7 N1 C8 108.78(10) . . ? C7 N1 H1 125.6 . . ? C8 N1 H1 125.6 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 127.17(13) . . ? O1 C2 C7 115.33(12) . . ? C3 C2 C7 117.50(14) . . ? C2 C3 C4 120.94(14) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 122.22(14) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 C6 118.37(14) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C7 C6 C5 118.91(13) . . ? C7 C6 C9 106.94(11) . . ? C5 C6 C9 134.15(13) . . ? N1 C7 C6 108.36(12) . . ? N1 C7 C2 129.62(13) . . ? C6 C7 C2 122.02(13) . . ? N1 C8 C9 109.70(12) . . ? N1 C8 C16 117.43(11) . . ? C9 C8 C16 132.80(12) . . ? C8 C9 C6 106.21(11) . . ? C8 C9 C10 129.27(13) . . ? C6 C9 C10 124.48(12) . . ? C15 C10 C11 117.89(13) . . ? C15 C10 C9 122.10(13) . . ? C11 C10 C9 119.92(13) . . ? C12 C11 C10 121.01(16) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 120.11(16) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.93(15) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 120.16(16) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C10 120.90(15) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? O2 C16 O3 123.31(13) . . ? O2 C16 C8 123.72(12) . . ? O3 C16 C8 112.94(11) . . ? O3 C17 C18 107.14(12) . . ? O3 C17 H17B 110.3 . . ? C18 C17 H17B 110.3 . . ? O3 C17 H17A 110.3 . . ? C18 C17 H17A 110.3 . . ? H17B C17 H17A 108.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? H18C C18 H18B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.129 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.027