Supplementary Information (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_mn1025 _database_code_CSD 152984 #SUBMISSION DETAILS _journal_coden_Cambridge 182 _publ_requested_journal Chem. Commun. _publ_contact_author 'Prof Mark J. Kurth' _publ_contact_author_address ; Mark J. Kurth Department of Chemistry University of California Davis, CA 95616 USA ; publ_contact_author_email mjkurth@ucdavis.edu _publ_section_title ; 4-Hydroxy-3-(2'-pyridyl)coumarins by Intramolecular Nucleophilic Aromatic Substitution ; loop_ _publ_author_name _publ_author_address 'Concepcion Alonso' ;Department of Chemistry University of California One Shields Ave Davis, CA 95616 USA ; 'Marilyn M. Olmstead' ;Department of Chemistry University of California One Shields Ave Davis, CA 95616 USA ; 'Michael H. Nantz' ;Department of Chemistry University of California One Shields Ave Davis, CA 95616 USA ; 'Mark J. Kurth' ;Department of Chemistry University of California One Shields Ave Davis, CA 95616 USA ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; phenylmethyl 9-chloro-6-oxa-10b-hydropyridino[1,2-a]quinoline-5-carboxylate ; _chemical_name_common 'Compound 3a' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 Cl N O3' _chemical_formula_weight 363.78 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' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1272(9) _cell_length_b 9.5407(12) _cell_length_c 13.1738(10) _cell_angle_alpha 77.273(8) _cell_angle_beta 79.502(9) _cell_angle_gamma 68.701(10) _cell_volume 808.95(16) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 3.45 _cell_measurement_theta_max 32.7 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 2.280 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7408 _exptl_absorpt_correction_T_max 0.7715 _exptl_absorpt_process_details ;XABS2: an empirical absorption correction program. Parkin, S.; Moezzi, B.; Hope, H. J. Appl. Cryst. 1995, 28, 53-56. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Siemens rotating anode' _diffrn_radiation_monochromator 'nickel filter' _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 198 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.0 _diffrn_reflns_number 2105 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 56.09 _reflns_number_total 2105 _reflns_number_gt 1904 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3' _computing_cell_refinement 'Siemens P3' _computing_data_reduction 'Siemens XDISK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.03, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0310P)^2^+0.5496P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2105 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.003 _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 Cl1 Cl 0.83782(8) 0.76845(6) -0.35412(4) 0.02997(18) Uani 1 1 d . . . O1 O 0.6061(2) 0.78253(17) 0.15714(12) 0.0340(4) Uani 1 1 d . . . O2 O 0.6594(2) 0.41440(19) 0.34292(12) 0.0398(4) Uani 1 1 d . . . O3 O 0.3781(2) 0.59709(16) 0.28888(11) 0.0246(4) Uani 1 1 d . . . N N 0.7665(2) 0.42141(18) -0.00174(13) 0.0180(4) Uani 1 1 d . . . C1 C 0.7656(3) 0.5678(2) -0.05774(16) 0.0177(5) Uani 1 1 d . . . C2 C 0.8097(3) 0.5931(2) -0.16692(17) 0.0200(5) Uani 1 1 d . . . H2 H 0.847(3) 0.516(3) -0.2061(17) 0.023(6) Uiso 1 1 d . . . C3 C 0.7973(3) 0.7382(2) -0.21836(16) 0.0220(5) Uani 1 1 d . . . C4 C 0.7472(3) 0.8603(3) -0.16574(18) 0.0250(5) Uani 1 1 d . . . H4 H 0.734(3) 0.963(3) -0.2033(17) 0.028(6) Uiso 1 1 d . . . C5 C 0.7073(3) 0.8333(2) -0.05927(18) 0.0235(5) Uani 1 1 d . . . H5 H 0.665(3) 0.914(2) -0.0209(16) 0.018(5) Uiso 1 1 d . . . C6 C 0.7131(3) 0.6888(2) -0.00291(16) 0.0200(5) Uani 1 1 d . . . C7 C 0.6515(3) 0.6729(2) 0.11060(17) 0.0234(5) Uani 1 1 d . . . C8 C 0.6463(3) 0.5241(2) 0.15990(16) 0.0198(5) Uani 1 1 d . . . C9 C 0.5698(3) 0.5028(2) 0.27337(17) 0.0232(5) Uani 1 1 d . . . C10 C 0.2827(3) 0.5930(3) 0.39692(17) 0.0265(5) Uani 1 1 d . . . H10B H 0.279(3) 0.494(3) 0.4226(17) 0.028(6) Uiso 1 1 d . . . H10A H 0.366(3) 0.615(2) 0.4401(18) 0.030(6) Uiso 1 1 d . . . C11 C 0.0777(3) 0.7125(2) 0.39353(16) 0.0247(5) Uani 1 1 d . . . C12 C -0.0899(4) 0.6770(3) 0.38403(17) 0.0300(6) Uani 1 1 d . . . H12 H -0.073(4) 0.574(3) 0.3772(19) 0.039(7) Uiso 1 1 d . . . C13 C -0.2782(4) 0.7894(3) 0.37809(18) 0.0343(6) Uani 1 1 d . . . H13 H -0.398(4) 0.765(3) 0.369(2) 0.046(7) Uiso 1 1 d . . . C14 C -0.3009(4) 0.9381(3) 0.38195(18) 0.0342(6) Uani 1 1 d . . . H14 H -0.427(4) 1.012(3) 0.3794(18) 0.035(7) Uiso 1 1 d . . . C15 C -0.1353(4) 0.9755(3) 0.39108(18) 0.0330(6) Uani 1 1 d . . . H15 H -0.152(4) 1.077(3) 0.3951(19) 0.041(7) Uiso 1 1 d . . . C16 C 0.0524(4) 0.8630(3) 0.39643(17) 0.0282(5) Uani 1 1 d . . . H16 H 0.170(4) 0.886(3) 0.4043(18) 0.032(6) Uiso 1 1 d . . . C17 C 0.7078(3) 0.4025(2) 0.10577(16) 0.0193(5) Uani 1 1 d . . . C18 C 0.8176(3) 0.2998(2) -0.05525(18) 0.0213(5) Uani 1 1 d . . . H18 H 0.853(3) 0.321(2) -0.1264(18) 0.020(6) Uiso 1 1 d . . . C19 C 0.8105(3) 0.1623(2) -0.00693(18) 0.0236(5) Uani 1 1 d . . . H19 H 0.846(3) 0.084(3) -0.0479(19) 0.034(6) Uiso 1 1 d . . . C20 C 0.7541(3) 0.1372(3) 0.10209(18) 0.0254(5) Uani 1 1 d . . . H20 H 0.751(3) 0.042(3) 0.1363(18) 0.032(6) Uiso 1 1 d . . . C21 C 0.7069(3) 0.2526(2) 0.15573(18) 0.0225(5) Uani 1 1 d . . . H21 H 0.674(3) 0.241(2) 0.2281(18) 0.022(6) Uiso 1 1 d . . . 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 Cl1 0.0348(3) 0.0290(3) 0.0247(3) -0.0022(2) -0.0013(2) -0.0114(3) O1 0.0494(10) 0.0280(9) 0.0326(9) -0.0143(8) 0.0002(7) -0.0195(8) O2 0.0329(9) 0.0452(11) 0.0278(9) -0.0015(8) -0.0079(8) 0.0020(8) O3 0.0206(8) 0.0302(9) 0.0219(8) -0.0041(6) -0.0034(6) -0.0068(7) N 0.0143(9) 0.0159(9) 0.0250(10) -0.0044(7) -0.0034(7) -0.0053(7) C1 0.0104(10) 0.0167(11) 0.0288(12) -0.0040(9) -0.0054(9) -0.0063(9) C2 0.0149(11) 0.0204(12) 0.0265(12) -0.0084(10) -0.0022(9) -0.0055(9) C3 0.0149(11) 0.0255(12) 0.0273(12) -0.0036(10) -0.0032(9) -0.0089(9) C4 0.0241(12) 0.0208(13) 0.0326(14) -0.0029(10) -0.0020(10) -0.0119(10) C5 0.0209(12) 0.0206(12) 0.0340(14) -0.0108(10) -0.0012(10) -0.0102(10) C6 0.0143(11) 0.0224(12) 0.0273(12) -0.0067(9) -0.0032(9) -0.0091(9) C7 0.0200(11) 0.0256(12) 0.0283(12) -0.0078(10) -0.0036(9) -0.0095(10) C8 0.0140(10) 0.0220(12) 0.0252(11) -0.0061(9) -0.0051(9) -0.0055(9) C9 0.0226(12) 0.0223(12) 0.0267(12) -0.0055(10) -0.0063(10) -0.0074(10) C10 0.0292(13) 0.0287(14) 0.0208(12) -0.0041(10) -0.0018(10) -0.0092(11) C11 0.0255(12) 0.0304(13) 0.0193(11) -0.0052(9) -0.0009(9) -0.0110(10) C12 0.0347(14) 0.0345(14) 0.0258(12) -0.0100(10) -0.0003(10) -0.0160(12) C13 0.0273(14) 0.0474(17) 0.0321(14) -0.0094(11) -0.0042(10) -0.0149(12) C14 0.0253(14) 0.0397(16) 0.0308(14) -0.0039(11) -0.0056(10) -0.0033(12) C15 0.0394(15) 0.0281(14) 0.0306(13) -0.0030(11) -0.0044(11) -0.0113(12) C16 0.0286(13) 0.0323(14) 0.0275(13) -0.0038(10) -0.0047(10) -0.0147(11) C17 0.0111(10) 0.0240(12) 0.0254(12) -0.0028(9) -0.0066(8) -0.0075(9) C18 0.0186(11) 0.0223(12) 0.0270(13) -0.0085(10) -0.0050(9) -0.0078(9) C19 0.0182(11) 0.0185(12) 0.0357(13) -0.0074(10) -0.0067(10) -0.0047(9) C20 0.0190(12) 0.0185(13) 0.0380(14) -0.0016(11) -0.0063(10) -0.0058(10) C21 0.0168(11) 0.0223(12) 0.0274(13) -0.0016(10) -0.0050(9) -0.0057(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 Cl1 C3 1.735(2) . ? O1 C7 1.241(3) . ? O2 C9 1.200(3) . ? O3 C9 1.343(2) . ? O3 C10 1.460(3) . ? N C18 1.391(3) . ? N C17 1.393(3) . ? N C1 1.427(3) . ? C1 C6 1.396(3) . ? C1 C2 1.401(3) . ? C2 C3 1.379(3) . ? C2 H2 0.92(2) . ? C3 C4 1.389(3) . ? C4 C5 1.365(3) . ? C4 H4 0.97(2) . ? C5 C6 1.404(3) . ? C5 H5 0.94(2) . ? C6 C7 1.470(3) . ? C7 C8 1.435(3) . ? C8 C17 1.389(3) . ? C8 C9 1.491(3) . ? C10 C11 1.493(3) . ? C10 H10B 0.94(2) . ? C10 H10A 0.99(3) . ? C11 C12 1.387(3) . ? C11 C16 1.389(3) . ? C12 C13 1.383(3) . ? C12 H12 0.97(3) . ? C13 C14 1.380(4) . ? C13 H13 1.00(3) . ? C14 C15 1.382(4) . ? C14 H14 0.92(2) . ? C15 C16 1.380(3) . ? C15 H15 0.95(3) . ? C16 H16 0.97(2) . ? C17 C21 1.439(3) . ? C18 C19 1.341(3) . ? C18 H18 0.92(2) . ? C19 C20 1.411(3) . ? C19 H19 0.95(2) . ? C20 C21 1.346(3) . ? C20 H20 0.92(2) . ? C21 H21 0.93(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 C9 O3 C10 116.75(16) . . ? C18 N C17 120.23(17) . . ? C18 N C1 119.97(17) . . ? C17 N C1 119.75(16) . . ? C6 C1 C2 119.60(19) . . ? C6 C1 N 119.25(18) . . ? C2 C1 N 121.11(18) . . ? C3 C2 C1 119.2(2) . . ? C3 C2 H2 118.3(13) . . ? C1 C2 H2 122.5(13) . . ? C2 C3 C4 122.5(2) . . ? C2 C3 Cl1 118.10(17) . . ? C4 C3 Cl1 119.40(16) . . ? C5 C4 C3 117.6(2) . . ? C5 C4 H4 120.9(13) . . ? C3 C4 H4 121.4(13) . . ? C4 C5 C6 122.4(2) . . ? C4 C5 H5 120.5(12) . . ? C6 C5 H5 116.9(12) . . ? C1 C6 C5 118.70(19) . . ? C1 C6 C7 122.48(19) . . ? C5 C6 C7 118.71(19) . . ? O1 C7 C8 124.4(2) . . ? O1 C7 C6 120.95(19) . . ? C8 C7 C6 114.64(19) . . ? C17 C8 C7 122.49(19) . . ? C17 C8 C9 119.88(19) . . ? C7 C8 C9 117.62(18) . . ? O2 C9 O3 123.0(2) . . ? O2 C9 C8 127.00(19) . . ? O3 C9 C8 110.01(17) . . ? O3 C10 C11 106.23(17) . . ? O3 C10 H10B 107.9(14) . . ? C11 C10 H10B 113.7(14) . . ? O3 C10 H10A 109.4(13) . . ? C11 C10 H10A 111.1(13) . . ? H10B C10 H10A 108.3(19) . . ? C12 C11 C16 118.6(2) . . ? C12 C11 C10 120.9(2) . . ? C16 C11 C10 120.4(2) . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12 119.9(15) . . ? C11 C12 H12 119.5(15) . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13 119.2(15) . . ? C12 C13 H13 120.7(15) . . ? C13 C14 C15 120.2(2) . . ? C13 C14 H14 119.6(16) . . ? C15 C14 H14 120.3(16) . . ? C16 C15 C14 119.5(2) . . ? C16 C15 H15 120.7(15) . . ? C14 C15 H15 119.8(15) . . ? C15 C16 C11 121.1(2) . . ? C15 C16 H16 120.9(14) . . ? C11 C16 H16 117.9(14) . . ? C8 C17 N 121.23(18) . . ? C8 C17 C21 122.47(19) . . ? N C17 C21 116.25(18) . . ? C19 C18 N 122.1(2) . . ? C19 C18 H18 122.4(13) . . ? N C18 H18 115.5(13) . . ? C18 C19 C20 119.7(2) . . ? C18 C19 H19 118.3(14) . . ? C20 C19 H19 122.0(14) . . ? C21 C20 C19 119.2(2) . . ? C21 C20 H20 120.4(15) . . ? C19 C20 H20 120.4(15) . . ? C20 C21 C17 122.5(2) . . ? C20 C21 H21 122.7(13) . . ? C17 C21 H21 114.9(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 56.09 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.181 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.037