# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_email rmarvaz@unex.es _publ_contact_author_name 'R. Fernando Martinez' loop_ _publ_author_name 'R. Fernando Martinez' 'Martin Avalos' 'Reyes Babiano' 'Pedro Cintas' 'Jose L. Jimenez' ; M.E.Light ; 'Juan C. Palacios' data_2010acc0500 _database_code_depnum_ccdc_archive 'CCDC 805572' #TrackingRef 'web_deposit_cif_file_0_R.FernandoMartinez_1293020808.cif' _chemical_compound_source 'Pedro Cintas' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O' _chemical_formula_weight 303.39 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 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 8.0440(2) _cell_length_b 18.8305(8) _cell_length_c 11.1262(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.736(2) _cell_angle_gamma 90.00 _cell_volume 1650.08(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12509 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour Orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9853 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24247 _diffrn_reflns_av_R_equivalents 0.0866 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3779 _reflns_number_gt 2327 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. Long O-H Bond (0.82A) O1 - H901 ... 1.04 Ang. This was refined and indicates a degree of migration between O1 and N1 ; _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^)+(0.0864P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3779 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1634 _refine_ls_wR_factor_gt 0.1378 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.41283(16) 0.08827(8) 0.70801(13) 0.0366(4) Uani 1 1 d . . . H901 H 0.404(4) 0.1227(17) 0.780(3) 0.100(10) Uiso 1 1 d . . . N1 N 0.31439(17) 0.15050(8) 0.88560(13) 0.0258(4) Uani 1 1 d . . . C1 C 0.0213(2) 0.00344(9) 0.76519(17) 0.0281(4) Uani 1 1 d . . . C2 C -0.1046(2) 0.00670(10) 0.83710(18) 0.0330(5) Uani 1 1 d . . . H2 H -0.0963 0.0418 0.8993 0.040 Uiso 1 1 calc R . . C3 C -0.2387(3) -0.03981(11) 0.8189(2) 0.0413(5) Uani 1 1 d . . . H3 H -0.3215 -0.0364 0.8685 0.050 Uiso 1 1 calc R . . C4 C -0.2549(3) -0.09221(12) 0.7283(2) 0.0473(6) Uani 1 1 d . . . H4 H -0.3480 -0.1243 0.7162 0.057 Uiso 1 1 calc R . . C5 C -0.1358(3) -0.09670(12) 0.6576(2) 0.0442(6) Uani 1 1 d . . . H5 H -0.1472 -0.1322 0.5959 0.053 Uiso 1 1 calc R . . C6 C 0.0040(2) -0.05014(10) 0.67345(19) 0.0350(5) Uani 1 1 d . . . C7 C 0.1271(3) -0.05522(11) 0.5999(2) 0.0409(5) Uani 1 1 d . . . H7 H 0.1162 -0.0916 0.5396 0.049 Uiso 1 1 calc R . . C8 C 0.2599(3) -0.01018(11) 0.61219(18) 0.0379(5) Uani 1 1 d . . . H8 H 0.3404 -0.0149 0.5610 0.045 Uiso 1 1 calc R . . C9 C 0.2785(2) 0.04400(10) 0.70156(17) 0.0300(4) Uani 1 1 d . . . C10 C 0.1637(2) 0.05153(9) 0.77917(16) 0.0254(4) Uani 1 1 d . . . C11 C 0.1888(2) 0.10655(9) 0.87180(16) 0.0263(4) Uani 1 1 d . . . H11 H 0.1099 0.1105 0.9244 0.032 Uiso 1 1 calc R . . C12 C 0.3256(2) 0.20613(9) 0.97376(16) 0.0253(4) Uani 1 1 d . . . C13 C 0.1788(2) 0.24460(10) 0.97900(17) 0.0296(4) Uani 1 1 d . . . H13 H 0.0752 0.2326 0.9250 0.035 Uiso 1 1 calc R . . C14 C 0.1815(2) 0.29981(10) 1.06147(19) 0.0327(5) Uani 1 1 d . . . H14 H 0.0806 0.3252 1.0650 0.039 Uiso 1 1 calc R . . C15 C 0.3329(2) 0.31745(10) 1.13843(18) 0.0334(5) Uani 1 1 d . . . H15 H 0.3370 0.3552 1.1956 0.040 Uiso 1 1 calc R . . C16 C 0.4792(2) 0.27981(10) 1.13208(17) 0.0306(4) Uani 1 1 d . . . H16 H 0.5821 0.2928 1.1859 0.037 Uiso 1 1 calc R . . C17 C 0.4823(2) 0.22378(10) 1.05050(16) 0.0260(4) Uani 1 1 d . . . C18 C 0.6489(2) 0.18480(10) 1.04586(17) 0.0290(4) Uani 1 1 d . . . C19 C 0.6988(2) 0.19870(10) 0.92172(18) 0.0324(5) Uani 1 1 d . . . H19A H 0.7977 0.1697 0.9154 0.049 Uiso 1 1 calc R . . H19B H 0.7267 0.2490 0.9155 0.049 Uiso 1 1 calc R . . H19C H 0.6036 0.1862 0.8550 0.049 Uiso 1 1 calc R . . C20 C 0.6319(2) 0.10446(10) 1.06543(19) 0.0341(5) Uani 1 1 d . . . H20A H 0.5957 0.0961 1.1432 0.051 Uiso 1 1 calc R . . H20B H 0.7419 0.0814 1.0678 0.051 Uiso 1 1 calc R . . H20C H 0.5475 0.0846 0.9977 0.051 Uiso 1 1 calc R . . C21 C 0.7966(2) 0.21070(12) 1.14611(19) 0.0398(5) Uani 1 1 d . . . H21A H 0.7690 0.2029 1.2269 0.060 Uiso 1 1 calc R . . H21B H 0.8154 0.2615 1.1348 0.060 Uiso 1 1 calc R . . H21C H 0.8997 0.1842 1.1406 0.060 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 0.0354(7) 0.0395(8) 0.0376(8) -0.0035(7) 0.0141(6) -0.0036(6) N1 0.0266(7) 0.0249(8) 0.0252(8) -0.0005(6) 0.0034(6) 0.0012(6) C1 0.0297(9) 0.0240(10) 0.0280(10) 0.0022(8) -0.0004(7) 0.0032(7) C2 0.0325(10) 0.0317(11) 0.0337(11) 0.0011(9) 0.0045(8) -0.0010(8) C3 0.0380(11) 0.0386(12) 0.0469(13) 0.0027(10) 0.0075(9) -0.0089(9) C4 0.0463(12) 0.0387(12) 0.0530(15) -0.0015(11) 0.0010(11) -0.0156(10) C5 0.0524(13) 0.0348(12) 0.0420(13) -0.0079(10) 0.0013(10) -0.0099(10) C6 0.0388(11) 0.0280(11) 0.0351(12) -0.0007(9) 0.0002(9) 0.0003(8) C7 0.0516(12) 0.0340(12) 0.0358(12) -0.0089(9) 0.0058(10) -0.0009(10) C8 0.0456(12) 0.0386(12) 0.0306(11) -0.0054(9) 0.0105(9) 0.0055(9) C9 0.0314(10) 0.0285(10) 0.0292(11) 0.0028(8) 0.0043(8) 0.0031(8) C10 0.0282(9) 0.0231(10) 0.0235(10) 0.0037(7) 0.0022(7) 0.0051(7) C11 0.0242(9) 0.0273(10) 0.0270(10) 0.0039(8) 0.0040(7) 0.0040(7) C12 0.0296(9) 0.0241(9) 0.0234(10) 0.0011(7) 0.0080(7) -0.0029(7) C13 0.0267(9) 0.0296(10) 0.0336(11) -0.0014(8) 0.0089(8) -0.0024(7) C14 0.0335(10) 0.0314(11) 0.0378(12) -0.0005(9) 0.0179(8) -0.0002(8) C15 0.0403(11) 0.0321(11) 0.0314(11) -0.0062(8) 0.0157(9) -0.0069(8) C16 0.0332(9) 0.0327(11) 0.0263(10) -0.0016(8) 0.0066(8) -0.0080(8) C17 0.0279(9) 0.0276(10) 0.0233(10) 0.0024(8) 0.0070(7) -0.0040(7) C18 0.0264(9) 0.0319(10) 0.0283(11) 0.0013(8) 0.0044(8) 0.0009(7) C19 0.0270(9) 0.0348(11) 0.0371(12) -0.0009(9) 0.0103(8) -0.0009(8) C20 0.0294(10) 0.0336(11) 0.0382(12) 0.0071(9) 0.0045(8) 0.0020(8) C21 0.0294(10) 0.0464(13) 0.0407(13) -0.0006(10) 0.0001(9) -0.0033(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.355(2) . ? N1 C11 1.291(2) . ? N1 C12 1.425(2) . ? C1 C2 1.414(3) . ? C1 C6 1.422(3) . ? C1 C10 1.444(2) . ? C2 C3 1.372(3) . ? C3 C4 1.398(3) . ? C4 C5 1.360(3) . ? C5 C6 1.409(3) . ? C6 C7 1.411(3) . ? C7 C8 1.349(3) . ? C8 C9 1.411(3) . ? C9 C10 1.394(3) . ? C10 C11 1.446(3) . ? C12 C13 1.397(2) . ? C12 C17 1.411(2) . ? C13 C14 1.384(3) . ? C14 C15 1.379(3) . ? C15 C16 1.388(3) . ? C16 C17 1.395(3) . ? C17 C18 1.538(2) . ? C18 C21 1.534(3) . ? C18 C19 1.537(3) . ? C18 C20 1.539(3) . ? 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 C11 N1 C12 119.44(15) . . ? C2 C1 C6 117.41(17) . . ? C2 C1 C10 123.77(17) . . ? C6 C1 C10 118.82(18) . . ? C3 C2 C1 121.36(19) . . ? C2 C3 C4 120.9(2) . . ? C5 C4 C3 119.1(2) . . ? C4 C5 C6 121.9(2) . . ? C5 C6 C7 121.49(19) . . ? C5 C6 C1 119.4(2) . . ? C7 C6 C1 119.14(18) . . ? C8 C7 C6 122.23(19) . . ? C7 C8 C9 119.64(19) . . ? O1 C9 C10 121.75(17) . . ? O1 C9 C8 116.83(18) . . ? C10 C9 C8 121.42(18) . . ? C9 C10 C1 118.73(17) . . ? C9 C10 C11 120.02(16) . . ? C1 C10 C11 121.26(16) . . ? N1 C11 C10 122.44(17) . . ? C13 C12 C17 120.77(16) . . ? C13 C12 N1 118.30(15) . . ? C17 C12 N1 120.89(15) . . ? C14 C13 C12 121.18(16) . . ? C15 C14 C13 119.05(17) . . ? C14 C15 C16 119.74(18) . . ? C15 C16 C17 123.18(17) . . ? C16 C17 C12 116.07(16) . . ? C16 C17 C18 120.94(15) . . ? C12 C17 C18 123.00(16) . . ? C21 C18 C19 107.10(15) . . ? C21 C18 C17 112.03(16) . . ? C19 C18 C17 109.72(15) . . ? C21 C18 C20 106.70(15) . . ? C19 C18 C20 109.96(16) . . ? C17 C18 C20 111.21(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 O1 H901 N1 1.04(3) 1.59(3) 2.557(2) 152(3) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.198 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.056 # Attachment 'web_deposit_cif_file_1_R.FernandoMartinez_1293020808.cif' data_2010acc1162 _database_code_depnum_ccdc_archive 'CCDC 805573' #TrackingRef 'web_deposit_cif_file_1_R.FernandoMartinez_1293020808.cif' _chemical_compound_source 'Pedro Cintas' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 N O' _chemical_formula_weight 275.34 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 7.6826(2) _cell_length_b 12.2144(4) _cell_length_c 15.2964(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1435.39(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7390 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9754 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12111 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1470 _reflns_number_gt 1374 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0379P)^2^+0.2397P] 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 1470 _refine_ls_number_parameters 196 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 1.189 _refine_ls_restrained_S_all 1.193 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.002 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 0.0662(2) 0.01812(11) 0.16606(9) 0.0272(4) Uani 1 1 d D . . H901 H 0.030(4) -0.017(2) 0.1173(14) 0.056(9) Uiso 1 1 d D . . N1 N -0.0403(2) -0.01345(14) 0.01037(10) 0.0216(4) Uani 1 1 d . . . C1 C -0.0202(3) 0.28293(16) 0.05700(13) 0.0205(5) Uani 1 1 d . . . C2 C -0.0748(3) 0.33189(17) -0.02268(14) 0.0257(5) Uani 1 1 d . . . H2 H -0.1088 0.2864 -0.0701 0.031 Uiso 1 1 calc R . . C3 C -0.0796(3) 0.44329(17) -0.03249(15) 0.0275(5) Uani 1 1 d . . . H3 H -0.1172 0.4739 -0.0864 0.033 Uiso 1 1 calc R . . C4 C -0.0295(3) 0.51272(18) 0.03625(14) 0.0265(5) Uani 1 1 d . . . H4 H -0.0349 0.5899 0.0291 0.032 Uiso 1 1 calc R . . C5 C 0.0270(3) 0.46910(17) 0.11324(14) 0.0247(5) Uani 1 1 d . . . H5 H 0.0619 0.5163 0.1594 0.030 Uiso 1 1 calc R . . C6 C 0.0341(3) 0.35439(16) 0.12530(13) 0.0217(4) Uani 1 1 d . . . C7 C 0.0987(3) 0.30845(17) 0.20435(13) 0.0244(5) Uani 1 1 d . . . H7 H 0.1360 0.3559 0.2499 0.029 Uiso 1 1 calc R . . C8 C 0.1085(3) 0.19802(17) 0.21647(13) 0.0252(5) Uani 1 1 d . . . H8 H 0.1530 0.1693 0.2697 0.030 Uiso 1 1 calc R . . C9 C 0.0524(3) 0.12649(16) 0.14981(13) 0.0215(4) Uani 1 1 d . . . C10 C -0.0133(3) 0.16605(16) 0.07075(13) 0.0201(4) Uani 1 1 d . . . C11 C -0.0672(2) 0.09045(16) 0.00346(13) 0.0209(4) Uani 1 1 d . . . H11 H -0.1240 0.1179 -0.0472 0.025 Uiso 1 1 calc R . . C12 C -0.0896(3) -0.08673(16) -0.05756(13) 0.0208(4) Uani 1 1 d . . . C13 C -0.0447(3) -0.06948(17) -0.14548(13) 0.0247(5) Uani 1 1 d . . . C14 C -0.0964(3) -0.14831(18) -0.20627(14) 0.0299(5) Uani 1 1 d . . . H14 H -0.0677 -0.1385 -0.2662 0.036 Uiso 1 1 calc R . . C15 C -0.1887(3) -0.24050(19) -0.18127(15) 0.0316(5) Uani 1 1 d . . . H15 H -0.2243 -0.2924 -0.2239 0.038 Uiso 1 1 calc R . . C16 C -0.2288(3) -0.25697(17) -0.09418(15) 0.0281(5) Uani 1 1 d . . . H16 H -0.2913 -0.3207 -0.0773 0.034 Uiso 1 1 calc R . . C17 C -0.1791(3) -0.18172(17) -0.03110(14) 0.0229(5) Uani 1 1 d . . . C18 C 0.0579(3) 0.02826(18) -0.17714(14) 0.0309(5) Uani 1 1 d . . . H18A H 0.1256 0.0077 -0.2289 0.046 Uiso 1 1 calc R . . H18B H 0.1369 0.0528 -0.1308 0.046 Uiso 1 1 calc R . . H18C H -0.0223 0.0877 -0.1923 0.046 Uiso 1 1 calc R . . C19 C -0.2234(3) -0.19892(18) 0.06367(14) 0.0284(5) Uani 1 1 d . . . H19A H -0.2948 -0.2650 0.0698 0.043 Uiso 1 1 calc R . . H19B H -0.2882 -0.1355 0.0855 0.043 Uiso 1 1 calc R . . H19C H -0.1159 -0.2075 0.0975 0.043 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 0.0378(9) 0.0186(7) 0.0252(7) 0.0011(6) -0.0013(7) 0.0007(7) N1 0.0215(9) 0.0169(9) 0.0263(9) -0.0023(7) 0.0000(8) -0.0012(8) C1 0.0157(10) 0.0189(10) 0.0269(10) -0.0002(8) 0.0024(9) -0.0005(8) C2 0.0256(11) 0.0211(11) 0.0306(11) -0.0019(9) -0.0050(10) -0.0016(10) C3 0.0274(11) 0.0232(11) 0.0318(11) 0.0039(9) -0.0023(10) 0.0008(10) C4 0.0219(11) 0.0176(11) 0.0399(12) -0.0005(9) 0.0034(10) -0.0016(9) C5 0.0212(10) 0.0196(11) 0.0334(11) -0.0062(9) 0.0047(10) -0.0018(9) C6 0.0170(10) 0.0221(10) 0.0260(10) -0.0028(8) 0.0049(9) -0.0013(9) C7 0.0237(11) 0.0264(11) 0.0229(10) -0.0049(9) 0.0030(9) -0.0019(9) C8 0.0292(11) 0.0275(11) 0.0191(10) -0.0007(8) 0.0000(9) 0.0016(10) C9 0.0221(10) 0.0187(10) 0.0236(10) 0.0005(8) 0.0038(9) 0.0006(9) C10 0.0173(10) 0.0187(10) 0.0242(10) -0.0007(8) 0.0013(9) -0.0001(8) C11 0.0181(10) 0.0207(10) 0.0238(10) 0.0007(8) -0.0001(9) -0.0009(9) C12 0.0189(9) 0.0172(10) 0.0264(10) -0.0010(8) -0.0039(9) 0.0029(8) C13 0.0221(10) 0.0235(11) 0.0285(10) 0.0013(9) -0.0015(9) 0.0057(9) C14 0.0292(11) 0.0342(12) 0.0263(10) -0.0049(9) -0.0015(10) 0.0087(11) C15 0.0281(11) 0.0297(12) 0.0369(12) -0.0148(10) -0.0055(10) 0.0045(11) C16 0.0225(11) 0.0199(10) 0.0419(12) -0.0061(10) -0.0038(10) 0.0011(9) C17 0.0186(10) 0.0197(10) 0.0304(11) -0.0007(9) -0.0020(9) 0.0024(9) C18 0.0330(13) 0.0306(12) 0.0291(11) 0.0047(9) 0.0043(10) 0.0028(11) C19 0.0264(11) 0.0250(11) 0.0338(11) 0.0034(9) -0.0011(10) -0.0031(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.351(2) . ? N1 C11 1.290(3) . ? N1 C12 1.423(2) . ? C1 C2 1.421(3) . ? C1 C6 1.424(3) . ? C1 C10 1.444(3) . ? C2 C3 1.369(3) . ? C3 C4 1.405(3) . ? C4 C5 1.363(3) . ? C5 C6 1.414(3) . ? C6 C7 1.422(3) . ? C7 C8 1.364(3) . ? C8 C9 1.410(3) . ? C9 C10 1.397(3) . ? C10 C11 1.444(3) . ? C12 C13 1.404(3) . ? C12 C17 1.408(3) . ? C13 C14 1.397(3) . ? C13 C18 1.510(3) . ? C14 C15 1.384(3) . ? C15 C16 1.382(3) . ? C16 C17 1.386(3) . ? C17 C19 1.504(3) . ? 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 C11 N1 C12 121.10(17) . . ? C2 C1 C6 117.26(18) . . ? C2 C1 C10 123.49(18) . . ? C6 C1 C10 119.24(18) . . ? C3 C2 C1 121.3(2) . . ? C2 C3 C4 120.7(2) . . ? C5 C4 C3 119.9(2) . . ? C4 C5 C6 120.8(2) . . ? C5 C6 C7 121.02(19) . . ? C5 C6 C1 120.01(18) . . ? C7 C6 C1 118.96(18) . . ? C8 C7 C6 121.66(19) . . ? C7 C8 C9 119.9(2) . . ? O1 C9 C10 121.78(18) . . ? O1 C9 C8 116.74(18) . . ? C10 C9 C8 121.47(19) . . ? C9 C10 C11 119.99(18) . . ? C9 C10 C1 118.78(17) . . ? C11 C10 C1 121.20(18) . . ? N1 C11 C10 121.67(18) . . ? C13 C12 C17 121.26(18) . . ? C13 C12 N1 122.66(18) . . ? C17 C12 N1 116.00(17) . . ? C14 C13 C12 117.7(2) . . ? C14 C13 C18 118.69(19) . . ? C12 C13 C18 123.64(19) . . ? C15 C14 C13 121.5(2) . . ? C16 C15 C14 119.9(2) . . ? C15 C16 C17 120.9(2) . . ? C16 C17 C12 118.7(2) . . ? C16 C17 C19 121.07(19) . . ? C12 C17 C19 120.17(18) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.162 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.039 _iucr_refine_instruction_details ; TITL 2010acc1162 in P2(1)2(1)2(1) CELL 0.71073 7.6826 12.2144 15.2964 90.000 90.000 90.000 ZERR 4.00 0.0002 0.0004 0.0004 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O UNIT 76 68 4 4 MERG 4 OMIT 2 0 0 OMIT 2 2 0 OMIT 1 0 1 SHEL 7 0.84 FMAP 2 PLAN 40 SIZE 0.22 0.28 0.32 ACTA 55.00 BOND L.S. 4 HTAB rem DFIX 0.84 O1 H901 TEMP -153.00 WGHT 0.037900 0.239700 FVAR 0.29897 O1 4 0.066117 0.018024 0.165904 11.00000 0.03734 0.01846 = 0.02565 0.00175 -0.00084 0.00083 H901 2 0.022002 -0.021723 0.109185 11.00000 0.06304 N1 3 -0.040307 -0.013433 0.010341 11.00000 0.02171 0.01718 = 0.02628 -0.00225 0.00008 -0.00110 C1 1 -0.020233 0.282926 0.056987 11.00000 0.01581 0.01900 = 0.02689 -0.00018 0.00232 -0.00044 C2 1 -0.074846 0.331900 -0.022669 11.00000 0.02560 0.02121 = 0.03078 -0.00195 -0.00494 -0.00168 AFIX 43 H2 2 -0.108761 0.286420 -0.070083 11.00000 -1.20000 AFIX 0 C3 1 -0.079621 0.443280 -0.032529 11.00000 0.02733 0.02337 = 0.03192 0.00381 -0.00235 0.00080 AFIX 43 H3 2 -0.117171 0.473913 -0.086409 11.00000 -1.20000 AFIX 0 C4 1 -0.029519 0.512736 0.036271 11.00000 0.02193 0.01779 = 0.03985 -0.00051 0.00338 -0.00148 AFIX 43 H4 2 -0.034992 0.589924 0.029153 11.00000 -1.20000 AFIX 0 C5 1 0.026942 0.469103 0.113232 11.00000 0.02130 0.01966 = 0.03331 -0.00627 0.00465 -0.00175 AFIX 43 H5 2 0.061914 0.516337 0.159342 11.00000 -1.20000 AFIX 0 C6 1 0.034113 0.354400 0.125297 11.00000 0.01718 0.02234 = 0.02589 -0.00278 0.00476 -0.00130 C7 1 0.098726 0.308447 0.204334 11.00000 0.02386 0.02654 = 0.02309 -0.00485 0.00315 -0.00194 AFIX 43 H7 2 0.136010 0.355893 0.249843 11.00000 -1.20000 AFIX 0 C8 1 0.108507 0.198028 0.216436 11.00000 0.02930 0.02740 = 0.01931 -0.00068 -0.00008 0.00168 AFIX 43 H8 2 0.153031 0.169342 0.269656 11.00000 -1.20000 AFIX 0 C9 1 0.052389 0.126483 0.149782 11.00000 0.02206 0.01895 = 0.02352 0.00045 0.00374 0.00072 C10 1 -0.013301 0.166059 0.070712 11.00000 0.01736 0.01883 = 0.02458 -0.00073 0.00135 -0.00015 C11 1 -0.067221 0.090464 0.003437 11.00000 0.01805 0.02072 = 0.02393 0.00061 -0.00016 -0.00086 AFIX 43 H11 2 -0.123964 0.117907 -0.047206 11.00000 -1.20000 AFIX 0 C12 1 -0.089596 -0.086734 -0.057581 11.00000 0.01893 0.01734 = 0.02613 -0.00112 -0.00392 0.00277 C13 1 -0.044703 -0.069495 -0.145424 11.00000 0.02226 0.02349 = 0.02881 0.00123 -0.00157 0.00569 C14 1 -0.096416 -0.148339 -0.206267 11.00000 0.02931 0.03425 = 0.02635 -0.00508 -0.00158 0.00862 AFIX 43 H14 2 -0.067643 -0.138480 -0.266153 11.00000 -1.20000 AFIX 0 C15 1 -0.188643 -0.240502 -0.181244 11.00000 0.02822 0.02979 = 0.03695 -0.01473 -0.00550 0.00453 AFIX 43 H15 2 -0.224281 -0.292409 -0.223892 11.00000 -1.20000 AFIX 0 C16 1 -0.228833 -0.256947 -0.094181 11.00000 0.02249 0.01979 = 0.04216 -0.00621 -0.00382 0.00118 AFIX 43 H16 2 -0.291345 -0.320648 -0.077326 11.00000 -1.20000 AFIX 0 C17 1 -0.179114 -0.181697 -0.031123 11.00000 0.01869 0.01972 = 0.03035 -0.00071 -0.00213 0.00244 C18 1 0.057918 0.028246 -0.177159 11.00000 0.03301 0.03046 = 0.02937 0.00485 0.00441 0.00273 AFIX 137 H18A 2 0.125744 0.007595 -0.228852 11.00000 -1.50000 H18B 2 0.136860 0.052886 -0.130839 11.00000 -1.50000 H18C 2 -0.022284 0.087658 -0.192370 11.00000 -1.50000 AFIX 0 C19 1 -0.223331 -0.198907 0.063678 11.00000 0.02645 0.02512 = 0.03381 0.00337 -0.00110 -0.00307 AFIX 137 H19A 2 -0.294404 -0.265089 0.069807 11.00000 -1.50000 H19B 2 -0.288574 -0.135600 0.085482 11.00000 -1.50000 H19C 2 -0.115824 -0.207245 0.097513 11.00000 -1.50000 HKLF 4 REM 2010acc1162 in P2(1)2(1)2(1) REM R1 = 0.0330 for 1374 Fo > 4sig(Fo) and 0.0363 for all 1470 data REM 196 parameters refined using 0 restraints END WGHT 0.0386 0.3016 REM Highest difference peak 0.131, deepest hole -0.205, 1-sigma level 0.039 Q1 1 -0.0261 -0.0414 0.0626 11.00000 0.05 0.13 Q2 1 -0.0247 0.4811 0.1941 11.00000 0.05 0.12 Q3 1 -0.0285 0.3223 0.0995 11.00000 0.05 0.11 Q4 1 0.0004 0.1314 -0.1606 11.00000 0.05 0.11 Q5 1 -0.0130 0.2569 -0.0820 11.00000 0.05 0.11 Q6 1 -0.2091 -0.3180 0.0566 11.00000 0.05 0.11 Q7 1 0.0448 0.3511 0.2944 11.00000 0.05 0.11 Q8 1 -0.2738 -0.4000 -0.2171 11.00000 0.05 0.11 Q9 1 0.0112 0.4304 0.2605 11.00000 0.05 0.10 Q10 1 -0.0229 0.1729 -0.1027 11.00000 0.05 0.10 Q11 1 0.0822 -0.1050 0.1777 11.00000 0.05 0.10 Q12 1 -0.1068 -0.1542 0.1220 11.00000 0.05 0.10 Q13 1 -0.0242 0.2982 -0.1146 11.00000 0.05 0.10 Q14 1 0.1864 0.1658 -0.1368 11.00000 0.05 0.10 Q15 1 -0.3959 -0.3918 -0.0385 11.00000 0.05 0.10 Q16 1 0.0670 -0.0174 0.1225 11.00000 0.05 0.10 Q17 1 -0.1397 -0.0757 0.0746 11.00000 0.05 0.10 Q18 1 -0.1664 -0.0158 0.1245 11.00000 0.05 0.10 Q19 1 -0.2522 -0.4275 -0.0440 11.00000 0.05 0.10 Q20 1 -0.4074 -0.0475 0.1021 11.00000 0.05 0.10 Q21 1 0.1178 0.4179 0.3330 11.00000 0.05 0.10 Q22 1 0.0866 0.1780 -0.0817 11.00000 0.05 0.10 Q23 1 0.1159 0.0976 -0.1028 11.00000 0.05 0.10 Q24 1 0.2754 0.3802 0.1987 11.00000 0.05 0.09 Q25 1 0.0067 0.3974 0.1248 11.00000 0.05 0.09 Q26 1 -0.2840 -0.1286 0.1509 11.00000 0.05 0.09 Q27 1 -0.3679 -0.3828 -0.2728 11.00000 0.05 0.09 Q28 1 -0.0322 0.4768 -0.1780 11.00000 0.05 0.09 Q29 1 -0.0801 0.1592 -0.1601 11.00000 0.05 0.09 Q30 1 0.1749 0.3052 0.0244 11.00000 0.05 0.09 Q31 1 -0.0376 -0.1506 0.1473 11.00000 0.05 0.09 Q32 1 0.1765 0.3435 0.3007 11.00000 0.05 0.09 Q33 1 -0.0359 0.2412 -0.1738 11.00000 0.05 0.09 Q34 1 -0.2247 -0.3652 -0.0971 11.00000 0.05 0.09 Q35 1 -0.1446 -0.1458 0.1417 11.00000 0.05 0.09 Q36 1 -0.0242 0.2834 0.2923 11.00000 0.05 0.09 Q37 1 0.0900 -0.0396 0.2364 11.00000 0.05 0.09 Q38 1 -0.2793 -0.3461 -0.0155 11.00000 0.05 0.09 Q39 1 0.0008 0.0425 0.0012 11.00000 0.05 0.09 Q40 1 -0.3110 -0.3296 -0.1680 11.00000 0.05 0.08 ; # Attachment 'web_deposit_cif_file_2_R.FernandoMartinez_1293020808.cif' data_2010acc0501 _database_code_depnum_ccdc_archive 'CCDC 805574' #TrackingRef 'web_deposit_cif_file_2_R.FernandoMartinez_1293020808.cif' _chemical_compound_source 'Pedro Cintas' _database_code_CSD 10AC0501 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 N O' _chemical_formula_weight 275.34 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4367(3) _cell_length_b 7.7374(3) _cell_length_c 11.1697(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.964(3) _cell_angle_gamma 90.00 _cell_volume 729.03(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8909 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9847 _exptl_absorpt_correction_T_max 0.9985 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 7946 reflections reduced R(int) from 0.0830 to 0.0447 Ratio of minimum to maximum apparent transmission: 0.826137 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8693 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1772 _reflns_number_gt 1448 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0319P)^2^+0.2795P] 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 1772 _refine_ls_number_parameters 196 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1174 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_restrained_S_all 1.206 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.002 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 0.7443(2) 0.2043(3) 0.34083(18) 0.0307(5) Uani 1 1 d . . . H1 H 0.649(5) 0.239(7) 0.281(4) 0.082(15) Uiso 1 1 d . . . N1 N 0.4771(3) 0.3111(4) 0.2590(2) 0.0261(6) Uani 1 1 d . . . C1 C 0.6910(4) 0.2389(4) 0.4503(3) 0.0269(7) Uani 1 1 d . . . C2 C 0.7969(4) 0.2108(4) 0.5504(3) 0.0269(7) Uani 1 1 d . . . C3 C 0.9513(4) 0.1461(5) 0.5347(3) 0.0339(8) Uani 1 1 d . . . H3 H 0.9864 0.1184 0.4567 0.041 Uiso 1 1 calc R . . C4 C 1.0515(4) 0.1230(5) 0.6315(3) 0.0397(9) Uani 1 1 d . . . H4 H 1.1559 0.0805 0.6204 0.048 Uiso 1 1 calc R . . C5 C 0.9992(4) 0.1624(5) 0.7471(3) 0.0393(9) Uani 1 1 d . . . H5 H 1.0692 0.1468 0.8137 0.047 Uiso 1 1 calc R . . C6 C 0.8497(4) 0.2224(5) 0.7652(3) 0.0367(8) Uani 1 1 d . . . H6 H 0.8164 0.2473 0.8442 0.044 Uiso 1 1 calc R . . C7 C 0.7435(4) 0.2481(4) 0.6674(3) 0.0301(7) Uani 1 1 d . . . C8 C 0.5859(4) 0.3091(5) 0.6832(3) 0.0344(8) Uani 1 1 d . . . H8 H 0.5491 0.3317 0.7615 0.041 Uiso 1 1 calc R . . C9 C 0.4878(4) 0.3351(5) 0.5872(3) 0.0320(8) Uani 1 1 d . . . H9 H 0.3832 0.3762 0.5997 0.038 Uiso 1 1 calc R . . C10 C 0.5383(4) 0.3021(4) 0.4683(3) 0.0270(7) Uani 1 1 d . . . C11 C 0.4345(4) 0.3399(4) 0.3674(3) 0.0276(7) Uani 1 1 d . . . H11 H 0.3326 0.3871 0.3814 0.033 Uiso 1 1 calc R . . C12 C 0.3820(3) 0.3571(4) 0.1580(3) 0.0250(7) Uani 1 1 d . . . C13 C 0.4610(4) 0.4462(4) 0.0669(3) 0.0293(7) Uani 1 1 d . . . C14 C 0.3767(4) 0.4935(5) -0.0358(3) 0.0338(8) Uani 1 1 d . . . H14 H 0.4285 0.5556 -0.0973 0.041 Uiso 1 1 calc R . . C15 C 0.2181(4) 0.4509(5) -0.0496(3) 0.0361(8) Uani 1 1 d . . . H15 H 0.1611 0.4843 -0.1199 0.043 Uiso 1 1 calc R . . C16 C 0.1431(4) 0.3595(5) 0.0394(3) 0.0344(8) Uani 1 1 d . . . H16 H 0.0347 0.3292 0.0286 0.041 Uiso 1 1 calc R . . C17 C 0.2225(3) 0.3107(4) 0.1447(3) 0.0286(7) Uani 1 1 d . . . C18 C 0.6343(4) 0.4904(5) 0.0815(3) 0.0379(8) Uani 1 1 d . . . H18A H 0.6500 0.5613 0.1534 0.057 Uiso 1 1 calc R . . H18B H 0.6692 0.5548 0.0111 0.057 Uiso 1 1 calc R . . H18C H 0.6962 0.3837 0.0893 0.057 Uiso 1 1 calc R . . C19 C 0.1350(4) 0.2094(5) 0.2375(3) 0.0402(9) Uani 1 1 d . . . H19A H 0.0877 0.2892 0.2950 0.060 Uiso 1 1 calc R . . H19B H 0.2090 0.1321 0.2797 0.060 Uiso 1 1 calc R . . H19C H 0.0512 0.1410 0.1984 0.060 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 0.0290(11) 0.0406(14) 0.0225(11) 0.0029(11) 0.0021(9) 0.0004(11) N1 0.0269(12) 0.0256(14) 0.0257(13) 0.0007(12) -0.0005(10) -0.0020(12) C1 0.0318(16) 0.0256(17) 0.0233(15) 0.0026(14) 0.0039(12) -0.0043(14) C2 0.0318(15) 0.0222(17) 0.0266(15) 0.0027(14) -0.0011(12) -0.0064(14) C3 0.0339(17) 0.035(2) 0.0329(18) 0.0056(15) 0.0004(14) -0.0001(15) C4 0.0379(18) 0.037(2) 0.043(2) 0.0073(18) -0.0057(15) 0.0000(17) C5 0.047(2) 0.034(2) 0.0366(19) 0.0049(16) -0.0147(16) -0.0052(17) C6 0.055(2) 0.0286(19) 0.0263(17) 0.0016(15) -0.0088(15) -0.0058(17) C7 0.0400(17) 0.0229(18) 0.0273(16) 0.0022(13) -0.0010(13) -0.0038(14) C8 0.049(2) 0.0311(19) 0.0232(15) -0.0008(15) 0.0040(14) 0.0005(17) C9 0.0369(17) 0.0278(19) 0.0316(16) -0.0010(15) 0.0051(13) 0.0032(15) C10 0.0346(16) 0.0215(16) 0.0249(15) 0.0003(14) 0.0009(12) 0.0002(14) C11 0.0270(15) 0.0225(17) 0.0334(17) 0.0042(14) 0.0033(12) 0.0006(13) C12 0.0266(14) 0.0221(16) 0.0262(15) -0.0009(13) -0.0012(12) 0.0041(13) C13 0.0310(15) 0.0278(18) 0.0291(16) -0.0005(14) 0.0021(13) 0.0013(14) C14 0.0418(18) 0.0321(19) 0.0276(15) 0.0014(15) 0.0026(13) 0.0028(15) C15 0.0409(18) 0.036(2) 0.0314(16) -0.0031(16) -0.0084(13) 0.0095(17) C16 0.0282(15) 0.034(2) 0.0410(19) -0.0089(16) -0.0035(14) 0.0048(15) C17 0.0292(15) 0.0248(17) 0.0318(16) -0.0046(14) 0.0014(13) 0.0025(14) C18 0.0337(17) 0.040(2) 0.0403(18) 0.0106(18) 0.0026(14) -0.0064(16) C19 0.0295(17) 0.042(2) 0.050(2) 0.0029(19) 0.0038(15) -0.0016(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.337(3) . ? N1 C11 1.289(4) . ? N1 C12 1.418(4) . ? C1 C10 1.395(4) . ? C1 C2 1.436(4) . ? C2 C3 1.409(4) . ? C2 C7 1.419(4) . ? C3 C4 1.373(5) . ? C4 C5 1.405(5) . ? C5 C6 1.363(5) . ? C6 C7 1.415(4) . ? C7 C8 1.424(5) . ? C8 C9 1.358(4) . ? C9 C10 1.425(4) . ? C10 C11 1.445(4) . ? C12 C17 1.399(4) . ? C12 C13 1.406(4) . ? C13 C14 1.389(4) . ? C13 C18 1.507(4) . ? C14 C15 1.384(5) . ? C15 C16 1.382(5) . ? C16 C17 1.396(4) . ? C17 C19 1.503(5) . ? 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 C11 N1 C12 122.8(3) . . ? O1 C1 C10 121.8(3) . . ? O1 C1 C2 117.8(2) . . ? C10 C1 C2 120.3(3) . . ? C3 C2 C7 119.7(3) . . ? C3 C2 C1 121.4(3) . . ? C7 C2 C1 118.9(3) . . ? C4 C3 C2 120.4(3) . . ? C3 C4 C5 119.8(3) . . ? C6 C5 C4 121.1(3) . . ? C5 C6 C7 120.6(3) . . ? C6 C7 C2 118.4(3) . . ? C6 C7 C8 122.1(3) . . ? C2 C7 C8 119.5(3) . . ? C9 C8 C7 120.6(3) . . ? C8 C9 C10 121.4(3) . . ? C1 C10 C9 119.2(3) . . ? C1 C10 C11 120.5(3) . . ? C9 C10 C11 120.2(3) . . ? N1 C11 C10 121.5(3) . . ? C17 C12 C13 121.1(3) . . ? C17 C12 N1 123.4(3) . . ? C13 C12 N1 115.5(3) . . ? C14 C13 C12 119.0(3) . . ? C14 C13 C18 120.8(3) . . ? C12 C13 C18 120.3(3) . . ? C15 C14 C13 120.6(3) . . ? C16 C15 C14 119.7(3) . . ? C15 C16 C17 121.7(3) . . ? C16 C17 C12 117.8(3) . . ? C16 C17 C19 119.2(3) . . ? C12 C17 C19 122.9(3) . . ? 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 H1 N1 1.07(5) 1.57(5) 2.556(3) 151(4) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.186 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.046 _iucr_refine_instruction_details ; TITL 2010acc0501 in P2(1) CELL 0.71073 8.4367 7.7374 11.1697 90.000 90.964 90.000 ZERR 2.00 0.0003 0.0003 0.0005 0.000 0.003 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O UNIT 38 34 2 2 MERG 4 SHEL 7 0.77 FMAP 2 PLAN 20 SIZE 0.02 0.08 0.20 ACTA 55.00 HTAB O1 N1 BOND L.S. 4 TEMP -153.00 WGHT 0.031900 0.279500 FVAR 1.28779 O1 4 0.744280 0.204300 0.340832 11.00000 0.02901 0.04063 = 0.02249 0.00292 0.00211 0.00044 H1 2 0.649061 0.238946 0.281428 11.00000 0.08155 N1 3 0.477075 0.311054 0.258977 11.00000 0.02688 0.02557 = 0.02572 0.00070 -0.00052 -0.00198 C1 1 0.690969 0.238885 0.450330 11.00000 0.03180 0.02563 = 0.02329 0.00265 0.00393 -0.00435 C2 1 0.796933 0.210784 0.550406 11.00000 0.03182 0.02216 = 0.02665 0.00272 -0.00107 -0.00639 C3 1 0.951342 0.146142 0.534731 11.00000 0.03393 0.03483 = 0.03291 0.00560 0.00045 -0.00012 AFIX 43 H3 2 0.986351 0.118398 0.456656 11.00000 -1.20000 AFIX 0 C4 1 1.051516 0.122987 0.631513 11.00000 0.03794 0.03749 = 0.04338 0.00734 -0.00570 -0.00003 AFIX 43 H4 2 1.155876 0.080489 0.620372 11.00000 -1.20000 AFIX 0 C5 1 0.999184 0.162350 0.747094 11.00000 0.04712 0.03355 = 0.03665 0.00492 -0.01468 -0.00524 AFIX 43 H5 2 1.069210 0.146831 0.813721 11.00000 -1.20000 AFIX 0 C6 1 0.849688 0.222410 0.765243 11.00000 0.05500 0.02858 = 0.02634 0.00160 -0.00883 -0.00579 AFIX 43 H6 2 0.816446 0.247270 0.844237 11.00000 -1.20000 AFIX 0 C7 1 0.743500 0.248077 0.667419 11.00000 0.04000 0.02294 = 0.02732 0.00220 -0.00100 -0.00381 C8 1 0.585924 0.309050 0.683171 11.00000 0.04903 0.03108 = 0.02317 -0.00084 0.00400 0.00045 AFIX 43 H8 2 0.549116 0.331725 0.761535 11.00000 -1.20000 AFIX 0 C9 1 0.487781 0.335084 0.587219 11.00000 0.03689 0.02775 = 0.03159 -0.00102 0.00510 0.00316 AFIX 43 H9 2 0.383230 0.376166 0.599654 11.00000 -1.20000 AFIX 0 C10 1 0.538329 0.302079 0.468297 11.00000 0.03457 0.02149 = 0.02488 0.00034 0.00089 0.00022 C11 1 0.434544 0.339867 0.367441 11.00000 0.02704 0.02247 = 0.03337 0.00418 0.00329 0.00056 AFIX 43 H11 2 0.332561 0.387058 0.381419 11.00000 -1.20000 AFIX 0 C12 1 0.382028 0.357112 0.158022 11.00000 0.02658 0.02212 = 0.02619 -0.00087 -0.00121 0.00412 C13 1 0.461017 0.446236 0.066945 11.00000 0.03104 0.02777 = 0.02909 -0.00048 0.00211 0.00126 C14 1 0.376741 0.493458 -0.035833 11.00000 0.04177 0.03209 = 0.02762 0.00135 0.00264 0.00280 AFIX 43 H14 2 0.428455 0.555568 -0.097283 11.00000 -1.20000 AFIX 0 C15 1 0.218141 0.450879 -0.049561 11.00000 0.04091 0.03581 = 0.03136 -0.00305 -0.00843 0.00947 AFIX 43 H15 2 0.161101 0.484325 -0.119865 11.00000 -1.20000 AFIX 0 C16 1 0.143119 0.359529 0.039408 11.00000 0.02823 0.03402 = 0.04095 -0.00887 -0.00346 0.00484 AFIX 43 H16 2 0.034714 0.329158 0.028616 11.00000 -1.20000 AFIX 0 C17 1 0.222457 0.310706 0.144732 11.00000 0.02922 0.02479 = 0.03181 -0.00456 0.00137 0.00255 C18 1 0.634258 0.490382 0.081468 11.00000 0.03373 0.03968 = 0.04026 0.01063 0.00261 -0.00642 AFIX 137 H18A 2 0.650046 0.561306 0.153376 11.00000 -1.50000 H18B 2 0.669198 0.554842 0.011147 11.00000 -1.50000 H18C 2 0.696183 0.383704 0.089325 11.00000 -1.50000 AFIX 0 C19 1 0.134959 0.209444 0.237532 11.00000 0.02950 0.04163 = 0.04969 0.00287 0.00377 -0.00157 AFIX 137 H19A 2 0.087662 0.289210 0.294974 11.00000 -1.50000 H19B 2 0.208999 0.132079 0.279694 11.00000 -1.50000 H19C 2 0.051162 0.141018 0.198438 11.00000 -1.50000 HKLF 4 REM 2010acc0501 in P2(1) REM R1 = 0.0538 for 1448 Fo > 4sig(Fo) and 0.0739 for all 1772 data REM 196 parameters refined using 1 restraints END WGHT 0.0258 0.4221 REM Highest difference peak 0.186, deepest hole -0.196, 1-sigma level 0.046 Q1 1 0.7545 0.2939 0.3751 11.00000 0.05 0.19 Q2 1 0.8839 0.2344 0.5381 11.00000 0.05 0.18 Q3 1 0.5654 0.2420 0.2400 11.00000 0.05 0.18 Q4 1 0.6419 0.5066 0.6363 11.00000 0.05 0.18 Q5 1 1.1129 0.2946 0.6191 11.00000 0.05 0.17 Q6 1 0.0048 0.2393 -0.0304 11.00000 0.05 0.16 Q7 1 0.8872 0.1292 0.3447 11.00000 0.05 0.16 Q8 1 0.6043 0.4976 -0.1159 11.00000 0.05 0.16 Q9 1 0.5569 0.6866 0.2174 11.00000 0.05 0.16 Q10 1 0.5073 0.0959 0.2756 11.00000 0.05 0.16 Q11 1 0.4077 0.6940 0.0807 11.00000 0.05 0.16 Q12 1 0.4769 0.5502 0.3364 11.00000 0.05 0.15 Q13 1 0.5605 0.4603 0.2590 11.00000 0.05 0.15 Q14 1 0.3791 0.1081 0.5268 11.00000 0.05 0.15 Q15 1 0.8043 0.0477 0.8597 11.00000 0.05 0.15 Q16 1 0.1938 0.3463 -0.0259 11.00000 0.05 0.15 Q17 1 0.5842 0.4739 0.4785 11.00000 0.05 0.15 Q18 1 0.5765 0.5815 0.2961 11.00000 0.05 0.15 Q19 1 0.4146 0.7339 0.0015 11.00000 0.05 0.14 Q20 1 0.1594 0.6427 -0.1635 11.00000 0.05 0.14 ; data_2010acc0779 _database_code_depnum_ccdc_archive 'CCDC 810937' #TrackingRef 'web_deposit_cif_file_0_R.FernandoMartinez_1296555467.cif' _chemical_compound_source 'Pedro Cintas' _database_code_CSD 10AC0779 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NAFTBU _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O' _chemical_formula_weight 303.39 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 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 8.5131(2) _cell_length_b 12.4731(4) _cell_length_c 15.8417(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.012(2) _cell_angle_gamma 90.00 _cell_volume 1638.95(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17297 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9779 _exptl_absorpt_correction_T_max 0.9955 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20079 _diffrn_reflns_av_R_equivalents 0.0727 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3746 _reflns_number_gt 2486 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. The hydrogen H901/H902 is modelled as disordered (50:50) between the oxygen O1 and the nitrogen N1. The evidence for this can be seen in the elongated bond lengths of C1-O1, and examination of the difference map. Whilst the electron density is somewhat smeared along a line between N1 and O1 2 distinct maxima can be seen corresponding to localised positions on N1 and O1 respectively, i.e. it does not appear to be located half way between the two atoms. ; _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^)+(0.0830P)^2^+0.0946P] 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 3746 _refine_ls_number_parameters 212 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1604 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _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 C1 C 0.4309(2) 0.24450(13) 0.05201(11) 0.0262(4) Uani 1 1 d . . . C2 C 0.5448(2) 0.17770(14) 0.02176(11) 0.0276(4) Uani 1 1 d . . . C3 C 0.7052(2) 0.16865(15) 0.07007(12) 0.0318(4) Uani 1 1 d . . . H3 H 0.7365 0.2033 0.1247 0.038 Uiso 1 1 calc R . . C4 C 0.8156(2) 0.11056(17) 0.03886(13) 0.0417(5) Uani 1 1 d . . . H4 H 0.9239 0.1062 0.0710 0.050 Uiso 1 1 calc R . . C5 C 0.7687(3) 0.05738(18) -0.04073(14) 0.0470(6) Uani 1 1 d . . . H5 H 0.8457 0.0163 -0.0618 0.056 Uiso 1 1 calc R . . C6 C 0.6137(3) 0.06362(16) -0.08861(13) 0.0410(5) Uani 1 1 d . . . H6 H 0.5843 0.0266 -0.1422 0.049 Uiso 1 1 calc R . . C7 C 0.4970(2) 0.12471(14) -0.05901(12) 0.0327(4) Uani 1 1 d . . . C8 C 0.3354(2) 0.13578(15) -0.10852(12) 0.0361(5) Uani 1 1 d . . . H8 H 0.3025 0.0989 -0.1620 0.043 Uiso 1 1 calc R . . C9 C 0.2289(2) 0.19870(15) -0.07950(12) 0.0336(4) Uani 1 1 d . . . H9 H 0.1217 0.2045 -0.1131 0.040 Uiso 1 1 calc R . . C10 C 0.2730(2) 0.25665(14) 0.00031(11) 0.0274(4) Uani 1 1 d . . . C11 C 0.1633(2) 0.32874(14) 0.02609(11) 0.0292(4) Uani 1 1 d . . . H11 H 0.0582 0.3365 -0.0097 0.035 Uiso 1 1 calc R . . C12 C 0.09236(19) 0.45215(14) 0.12785(11) 0.0261(4) Uani 1 1 d . . . C13 C -0.0674(2) 0.41888(15) 0.11508(12) 0.0317(4) Uani 1 1 d . . . H13 H -0.1002 0.3544 0.0842 0.038 Uiso 1 1 calc R . . C14 C -0.1793(2) 0.47791(16) 0.14660(12) 0.0361(5) Uani 1 1 d . . . H14 H -0.2885 0.4552 0.1366 0.043 Uiso 1 1 calc R . . C15 C -0.1298(2) 0.57006(16) 0.19273(12) 0.0358(5) Uani 1 1 d . . . H15 H -0.2050 0.6111 0.2153 0.043 Uiso 1 1 calc R . . C16 C 0.0293(2) 0.60332(15) 0.20637(11) 0.0316(4) Uani 1 1 d . . . H16 H 0.0604 0.6671 0.2386 0.038 Uiso 1 1 calc R . . C17 C 0.14601(19) 0.54681(14) 0.17467(11) 0.0261(4) Uani 1 1 d . . . C18 C 0.3218(2) 0.58776(14) 0.19119(11) 0.0293(4) Uani 1 1 d . . . C19 C 0.4352(2) 0.50979(16) 0.25128(11) 0.0342(5) Uani 1 1 d . . . H19A H 0.5435 0.5409 0.2675 0.051 Uiso 1 1 calc R . . H19B H 0.4396 0.4417 0.2211 0.051 Uiso 1 1 calc R . . H19C H 0.3945 0.4971 0.3036 0.051 Uiso 1 1 calc R . . C20 C 0.3741(2) 0.60224(16) 0.10503(12) 0.0341(5) Uani 1 1 d . . . H20A H 0.3013 0.6528 0.0682 0.051 Uiso 1 1 calc R . . H20B H 0.3700 0.5329 0.0755 0.051 Uiso 1 1 calc R . . H20C H 0.4845 0.6302 0.1165 0.051 Uiso 1 1 calc R . . C21 C 0.3400(2) 0.69715(17) 0.23688(14) 0.0449(5) Uani 1 1 d . . . H21A H 0.3139 0.6900 0.2938 0.067 Uiso 1 1 calc R . . H21B H 0.2665 0.7489 0.2018 0.067 Uiso 1 1 calc R . . H21C H 0.4513 0.7224 0.2442 0.067 Uiso 1 1 calc R . . N1 N 0.20236(16) 0.38453(11) 0.09719(9) 0.0261(3) Uani 1 1 d . . . H902 H 0.3021 0.3802 0.1279 0.031 Uiso 0.50 1 calc PR . . O1 O 0.47903(13) 0.29526(10) 0.12595(7) 0.0306(3) Uani 1 1 d . . . H901 H 0.3986 0.3204 0.1417 0.046 Uiso 0.50 1 calc PR . . 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 0.0343(9) 0.0218(9) 0.0239(9) 0.0007(7) 0.0095(7) -0.0015(7) C2 0.0352(10) 0.0224(9) 0.0271(9) 0.0047(7) 0.0107(7) 0.0013(7) C3 0.0376(10) 0.0300(10) 0.0292(10) 0.0042(8) 0.0104(7) 0.0059(8) C4 0.0432(11) 0.0481(13) 0.0353(11) 0.0081(9) 0.0122(9) 0.0182(9) C5 0.0577(13) 0.0496(13) 0.0382(12) 0.0052(10) 0.0201(10) 0.0250(11) C6 0.0598(13) 0.0354(11) 0.0314(11) -0.0014(9) 0.0177(9) 0.0112(9) C7 0.0457(11) 0.0247(9) 0.0297(10) 0.0018(8) 0.0129(8) 0.0032(8) C8 0.0484(11) 0.0284(10) 0.0304(10) -0.0051(8) 0.0068(8) -0.0014(8) C9 0.0372(10) 0.0299(10) 0.0315(10) -0.0025(8) 0.0029(8) -0.0032(8) C10 0.0302(9) 0.0248(9) 0.0270(9) 0.0000(7) 0.0063(7) -0.0017(7) C11 0.0285(9) 0.0294(10) 0.0294(10) 0.0024(8) 0.0057(7) -0.0026(7) C12 0.0265(9) 0.0280(9) 0.0248(9) 0.0041(7) 0.0078(7) 0.0025(7) C13 0.0298(9) 0.0313(10) 0.0345(10) 0.0003(8) 0.0083(7) -0.0039(7) C14 0.0251(9) 0.0461(12) 0.0379(11) 0.0054(9) 0.0090(8) 0.0005(8) C15 0.0320(10) 0.0456(12) 0.0325(10) 0.0048(9) 0.0129(8) 0.0111(8) C16 0.0342(10) 0.0342(11) 0.0264(10) 0.0008(8) 0.0072(7) 0.0056(8) C17 0.0272(8) 0.0291(10) 0.0223(9) 0.0043(7) 0.0059(6) 0.0034(7) C18 0.0277(9) 0.0290(10) 0.0308(10) -0.0042(8) 0.0058(7) -0.0014(7) C19 0.0302(9) 0.0449(12) 0.0261(10) -0.0030(8) 0.0033(7) 0.0013(8) C20 0.0335(10) 0.0379(11) 0.0310(10) 0.0034(8) 0.0076(8) -0.0068(8) C21 0.0407(11) 0.0397(12) 0.0530(13) -0.0126(10) 0.0083(9) -0.0026(9) N1 0.0274(7) 0.0238(8) 0.0279(8) 0.0005(6) 0.0080(6) 0.0001(6) O1 0.0310(6) 0.0320(7) 0.0285(7) -0.0057(5) 0.0062(5) 0.0023(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.3131(19) . ? C1 C10 1.417(2) . ? C1 C2 1.440(2) . ? C2 C3 1.411(2) . ? C2 C7 1.416(2) . ? C3 C4 1.364(3) . ? C4 C5 1.401(3) . ? C5 C6 1.368(3) . ? C6 C7 1.414(3) . ? C7 C8 1.428(3) . ? C8 C9 1.356(3) . ? C9 C10 1.431(2) . ? C10 C11 1.421(2) . ? C11 N1 1.302(2) . ? C12 C13 1.393(2) . ? C12 C17 1.414(2) . ? C12 N1 1.425(2) . ? C13 C14 1.383(3) . ? C14 C15 1.376(3) . ? C15 C16 1.386(3) . ? C16 C17 1.401(2) . ? C17 C18 1.547(2) . ? C18 C21 1.536(3) . ? C18 C20 1.539(3) . ? C18 C19 1.539(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 O1 C1 C10 121.94(15) . . ? O1 C1 C2 118.55(15) . . ? C10 C1 C2 119.48(15) . . ? C3 C2 C7 119.94(16) . . ? C3 C2 C1 120.49(16) . . ? C7 C2 C1 119.51(15) . . ? C4 C3 C2 120.46(18) . . ? C3 C4 C5 119.85(18) . . ? C6 C5 C4 121.06(18) . . ? C5 C6 C7 120.60(19) . . ? C6 C7 C2 118.08(17) . . ? C6 C7 C8 122.13(17) . . ? C2 C7 C8 119.78(16) . . ? C9 C8 C7 120.32(17) . . ? C8 C9 C10 121.97(17) . . ? C1 C10 C11 120.08(15) . . ? C1 C10 C9 118.87(16) . . ? C11 C10 C9 121.00(15) . . ? N1 C11 C10 122.04(15) . . ? C13 C12 C17 120.96(16) . . ? C13 C12 N1 118.01(16) . . ? C17 C12 N1 120.91(14) . . ? C14 C13 C12 121.23(17) . . ? C15 C14 C13 118.88(16) . . ? C14 C15 C16 120.28(17) . . ? C15 C16 C17 122.74(17) . . ? C16 C17 C12 115.89(15) . . ? C16 C17 C18 120.72(16) . . ? C12 C17 C18 123.39(15) . . ? C21 C18 C20 107.17(16) . . ? C21 C18 C19 106.69(14) . . ? C20 C18 C19 110.89(14) . . ? C21 C18 C17 111.35(15) . . ? C20 C18 C17 110.54(14) . . ? C19 C18 C17 110.11(14) . . ? C11 N1 C12 123.50(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 O1 H901 N1 0.84 1.84 2.5518(17) 141.1 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.193 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.054