# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/458 #ref. B004444J data_qn1_abs _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Cl2 N1 O2' _chemical_formula_sum 'C14 H9 Cl2 N1 O2' _chemical_formula_weight 294.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0170 0.0090 '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' 'Cl' 'Cl' 0.3480 0.7020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0470 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0290 0.0180 '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/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 22.123(3) _cell_length_b 7.040(1) _cell_length_c 15.937(3) _cell_angle_alpha 90.0(1) _cell_angle_beta 92.8(1) _cell_angle_gamma 90.0(1) _cell_volume 2479.2(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 105 _cell_measurement_theta_min 20 _cell_measurement_theta_max 40 _exptl_crystal_description ? _exptl_crystal_colour brown _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 4.687 _exptl_absorpt_correction_type 'gaussian' _exptl_absorpt_correction_T_min 0.1953 _exptl_absorpt_correction_T_max 0.4826 _exptl_absorpt_process_details '(Hall, 1982)' _exptl_special_details ; Ni filter used ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'no' _diffrn_measurement_device_type ; Stoe four circle diffractometer, microVAX controlled ; _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 3 _diffrn_reflns_number 4608 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.00 _diffrn_reflns_theta_max 67.03 _reflns_number_total 4434 _reflns_number_gt 3690 _reflns_threshold_expression >4sigma(Fo) _computing_data_collection 'STOE software' _computing_cell_refinement 'STOE software' _computing_data_reduction 'Stoe-routine REDUC' _computing_structure_solution 'SIR92 (Altomare, 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; SCHAKAL88 (Keller, 1988) ; _computing_publication_material ; SHELXL-93_ACTA (Sheldrick, 1993) ; _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^)+(0.0819P)^2^+0.9342P] 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 SHELXL _refine_ls_extinction_coef 0.00104(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4434 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 N101 N 0.74344(8) 0.1489(3) 0.45917(12) 0.0382(4) Uani 1 1 d . . . C102 C 0.74080(11) 0.1702(4) 0.36992(15) 0.0432(5) Uani 1 1 d . . . O102 O 0.78733(8) 0.1963(3) 0.33185(11) 0.0608(5) Uani 1 1 d . . . C103 C 0.68255(11) 0.1613(4) 0.32888(16) 0.0476(6) Uani 1 1 d . . . Cl1 Cl 0.67933(3) 0.18022(16) 0.22115(4) 0.0763(3) Uani 1 1 d . . . C104 C 0.62990(11) 0.1401(4) 0.37024(17) 0.0480(6) Uani 1 1 d . . . O104 O 0.57448(9) 0.1325(4) 0.33401(15) 0.0661(6) Uani 1 1 d . . . C105 C 0.63467(11) 0.1301(4) 0.45817(17) 0.0448(6) Uani 1 1 d . . . Cl2 Cl 0.56822(3) 0.11477(12) 0.50988(5) 0.0625(2) Uani 1 1 d . . . C106 C 0.68947(11) 0.1388(3) 0.50242(16) 0.0427(5) Uani 1 1 d . . . C107 C 0.69331(13) 0.1468(4) 0.59206(18) 0.0543(7) Uani 1 1 d . . . C108 C 0.74575(13) 0.1613(5) 0.63569(18) 0.0579(7) Uani 1 1 d . . . C109 C 0.80156(12) 0.1549(4) 0.59414(16) 0.0449(6) Uani 1 1 d . . . C110 C 0.85690(13) 0.1503(4) 0.64059(17) 0.0513(6) Uani 1 1 d . . . C111 C 0.91130(12) 0.1321(4) 0.60345(17) 0.0478(6) Uani 1 1 d . . . C112 C 0.90944(12) 0.1149(4) 0.51674(17) 0.0499(6) Uani 1 1 d . . . C113 C 0.85617(11) 0.1174(4) 0.46852(17) 0.0470(6) Uani 1 1 d . . . C114 C 0.80078(10) 0.1421(3) 0.50580(15) 0.0383(5) Uani 1 1 d . . . C115 C 0.97079(15) 0.1318(6) 0.6546(2) 0.0642(8) Uani 1 1 d . . . N201 N 0.97095(8) 0.2713(3) 0.05636(12) 0.0391(4) Uani 1 1 d . . . C202 C 0.97729(10) 0.2736(4) 0.14585(14) 0.0428(5) Uani 1 1 d . . . O202 O 1.02713(8) 0.2520(3) 0.18288(11) 0.0624(6) Uani 1 1 d . . . C203 C 0.92327(11) 0.3044(4) 0.18931(15) 0.0444(6) Uani 1 1 d . . . Cl3 Cl 0.93089(3) 0.31377(14) 0.29715(4) 0.0666(3) Uani 1 1 d . . . C204 C 0.86756(11) 0.3359(4) 0.15032(16) 0.0449(6) Uani 1 1 d . . . O204 O 0.81655(8) 0.3667(3) 0.18968(15) 0.0605(6) Uani 1 1 d . . . C205 C 0.86472(11) 0.3433(4) 0.06280(16) 0.0466(6) Uani 1 1 d . . . Cl4 Cl 0.79525(3) 0.38997(14) 0.01303(5) 0.0726(3) Uani 1 1 d . . . C206 C 0.91483(11) 0.3140(4) 0.01601(16) 0.0440(5) Uani 1 1 d . . . C207 C 0.91082(13) 0.3311(4) -0.07346(17) 0.0515(6) Uani 1 1 d . . . C208 C 0.95853(14) 0.3049(4) -0.11906(17) 0.0556(7) Uani 1 1 d . . . C209 C 1.01568(12) 0.2512(4) -0.08133(15) 0.0462(6) Uani 1 1 d . . . C210 C 1.06524(13) 0.2170(4) -0.13059(17) 0.0533(6) Uani 1 1 d . . . C211 C 1.12075(13) 0.1640(4) -0.09784(18) 0.0534(7) Uani 1 1 d . . . C212 C 1.12598(13) 0.1385(4) -0.01079(19) 0.0544(7) Uani 1 1 d . . . C213 C 1.07842(12) 0.1705(4) 0.04084(17) 0.0481(6) Uani 1 1 d . . . C214 C 1.02224(11) 0.2310(3) 0.00694(15) 0.0405(5) Uani 1 1 d . . . C215 C 1.17428(17) 0.1338(6) -0.1518(3) 0.0717(10) Uani 1 1 d . . . H104 H 0.5745(19) 0.145(6) 0.282(3) 0.089(13) Uiso 1 1 d . . . H107 H 0.6608(16) 0.144(4) 0.618(2) 0.068(10) Uiso 1 1 d . . . H108 H 0.7510(14) 0.177(4) 0.702(2) 0.063(9) Uiso 1 1 d . . . H110 H 0.8536(18) 0.159(5) 0.703(3) 0.092(12) Uiso 1 1 d . . . H112 H 0.9444(14) 0.099(4) 0.4924(19) 0.060(9) Uiso 1 1 d . . . H113 H 0.8561(15) 0.102(5) 0.413(2) 0.071(10) Uiso 1 1 d . . . H15A H 0.9657(16) 0.070(5) 0.701(2) 0.074(11) Uiso 1 1 d . . . H15B H 0.998(2) 0.067(7) 0.628(3) 0.124(17) Uiso 1 1 d . . . H15C H 0.9837(17) 0.264(5) 0.671(2) 0.076(11) Uiso 1 1 d . . . H204 H 0.820(2) 0.338(7) 0.235(3) 0.101(16) Uiso 1 1 d . . . H207 H 0.8744(14) 0.362(4) -0.0986(18) 0.049(8) Uiso 1 1 d . . . H208 H 0.9525(14) 0.321(4) -0.1839(19) 0.056(8) Uiso 1 1 d . . . H210 H 1.0604(13) 0.235(4) -0.1873(19) 0.047(7) Uiso 1 1 d . . . H212 H 1.1636(15) 0.101(4) 0.0147(19) 0.060(8) Uiso 1 1 d . . . H213 H 1.0876(13) 0.144(4) 0.0972(19) 0.050(8) Uiso 1 1 d . . . H15D H 1.201(2) 0.252(6) -0.141(3) 0.100(13) Uiso 1 1 d . . . H15E H 1.204(2) 0.030(6) -0.127(3) 0.095(13) Uiso 1 1 d . . . H15F H 1.1607(18) 0.117(6) -0.203(3) 0.086(13) 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 N101 0.0317(9) 0.0427(11) 0.0406(10) 0.0008(8) 0.0057(8) -0.0007(7) C102 0.0375(12) 0.0506(14) 0.0419(12) -0.0005(10) 0.0051(10) 0.0009(10) O102 0.0356(9) 0.1047(16) 0.0427(10) 0.0095(10) 0.0067(7) -0.0036(9) C103 0.0392(13) 0.0586(16) 0.0451(13) -0.0006(11) 0.0014(10) 0.0007(11) Cl1 0.0443(4) 0.1393(8) 0.0448(4) 0.0030(4) -0.0036(3) -0.0031(4) C104 0.0344(12) 0.0504(15) 0.0589(15) 0.0039(11) -0.0013(11) -0.0002(10) O104 0.0335(9) 0.0979(17) 0.0661(14) 0.0149(12) -0.0060(9) -0.0051(9) C105 0.0329(11) 0.0466(14) 0.0557(14) 0.0045(11) 0.0097(10) 0.0005(10) Cl2 0.0353(3) 0.0804(5) 0.0732(5) 0.0104(4) 0.0170(3) -0.0005(3) C106 0.0371(12) 0.0412(13) 0.0506(14) 0.0036(10) 0.0115(10) 0.0004(10) C107 0.0422(14) 0.0703(19) 0.0521(15) 0.0033(13) 0.0178(12) 0.0010(12) C108 0.0526(16) 0.079(2) 0.0431(14) -0.0006(13) 0.0108(12) -0.0009(14) C109 0.0435(13) 0.0484(14) 0.0432(13) 0.0009(10) 0.0052(10) -0.0009(10) C110 0.0518(15) 0.0605(17) 0.0414(13) -0.0003(12) -0.0002(11) -0.0007(12) C111 0.0448(13) 0.0491(15) 0.0493(14) -0.0010(11) -0.0017(11) 0.0019(11) C112 0.0389(13) 0.0599(16) 0.0511(14) -0.0014(12) 0.0040(11) 0.0039(11) C113 0.0387(13) 0.0600(16) 0.0427(13) -0.0023(12) 0.0053(10) 0.0020(11) C114 0.0367(12) 0.0356(12) 0.0427(12) 0.0007(9) 0.0029(9) -0.0006(9) C115 0.0521(17) 0.087(3) 0.0524(17) -0.0023(17) -0.0081(13) 0.0059(16) N201 0.0337(9) 0.0442(11) 0.0390(10) 0.0016(8) -0.0017(8) -0.0024(8) C202 0.0354(12) 0.0555(15) 0.0372(12) 0.0040(11) -0.0014(9) -0.0034(10) O202 0.0346(9) 0.1114(18) 0.0408(9) 0.0042(10) -0.0019(7) 0.0043(10) C203 0.0375(12) 0.0550(15) 0.0407(12) 0.0043(11) 0.0029(10) -0.0033(10) Cl3 0.0418(4) 0.1179(7) 0.0403(3) 0.0038(4) 0.0049(3) 0.0033(4) C204 0.0356(12) 0.0479(14) 0.0515(14) 0.0047(11) 0.0048(10) -0.0003(10) O204 0.0365(9) 0.0867(15) 0.0589(12) 0.0127(11) 0.0094(8) 0.0107(9) C205 0.0353(12) 0.0545(15) 0.0493(14) 0.0036(11) -0.0046(10) -0.0008(10) Cl4 0.0374(4) 0.1132(7) 0.0658(5) 0.0078(4) -0.0106(3) 0.0107(4) C206 0.0393(12) 0.0463(13) 0.0458(13) 0.0007(11) -0.0046(10) -0.0027(10) C207 0.0476(15) 0.0599(17) 0.0456(14) 0.0023(12) -0.0102(12) 0.0028(12) C208 0.0599(16) 0.0669(18) 0.0394(13) 0.0009(13) -0.0025(12) -0.0015(14) C209 0.0487(13) 0.0481(14) 0.0418(12) -0.0004(10) 0.0016(10) -0.0070(11) C210 0.0611(16) 0.0568(16) 0.0427(14) -0.0022(12) 0.0074(12) -0.0094(13) C211 0.0494(15) 0.0551(16) 0.0569(16) -0.0080(12) 0.0149(12) -0.0107(12) C212 0.0405(14) 0.0650(18) 0.0579(16) -0.0030(13) 0.0063(12) -0.0014(12) C213 0.0406(13) 0.0578(16) 0.0460(14) -0.0003(12) 0.0023(11) -0.0007(11) C214 0.0395(11) 0.0409(13) 0.0415(12) -0.0006(10) 0.0041(10) -0.0056(10) C215 0.0607(19) 0.090(3) 0.067(2) -0.0113(19) 0.0239(17) -0.0123(18) _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 N101 C106 1.409(3) . ? N101 C102 1.429(3) . ? N101 C114 1.439(3) . ? C102 O102 1.234(3) 1 ? C102 O102 1.234(3) . ? C102 C103 1.418(3) . ? O102 O102 0.000(6) 1 ? C103 C104 1.374(4) . ? C103 Cl1 1.720(3) . ? C104 O104 1.331(3) . ? C104 C105 1.402(4) . ? O104 H104 0.83(4) . ? C105 C106 1.374(4) . ? C105 Cl2 1.723(2) . ? C106 C107 1.428(4) . ? C107 C108 1.327(4) . ? C107 H107 0.85(4) . ? C108 C109 1.430(4) . ? C108 H108 1.06(3) . ? C109 C110 1.400(4) . ? C109 C114 1.410(3) . ? C110 C111 1.373(4) . ? C110 H110 1.00(4) . ? C111 C112 1.386(4) . ? C111 C115 1.514(4) . ? C112 C113 1.375(4) . ? C112 H112 0.89(3) . ? C113 C114 1.399(3) . ? C113 H113 0.90(3) . ? C115 H15A 0.87(4) . ? C115 H15B 0.89(5) . ? C115 H15C 1.01(4) . ? N201 C206 1.403(3) . ? N201 C202 1.426(3) . ? N201 C214 1.441(3) . ? C202 O202 1.234(3) . ? C202 C203 1.427(3) . ? C203 C204 1.371(3) . ? C203 Cl3 1.720(3) . ? C204 O204 1.335(3) . ? C204 C205 1.394(4) . ? O204 H204 0.76(4) . ? C205 C206 1.381(4) . ? C205 Cl4 1.726(2) . ? C206 C207 1.429(4) . ? C207 C208 1.324(4) . ? C207 H207 0.91(3) . ? C208 C209 1.424(4) . ? C208 H208 1.04(3) . ? C209 C210 1.400(4) . ? C209 C214 1.414(3) . ? C210 C211 1.363(4) . ? C210 H210 0.91(3) . ? C211 C212 1.398(4) . ? C211 C215 1.512(4) . ? C212 C213 1.385(4) . ? C212 H212 0.95(3) . ? C213 C214 1.397(4) . ? C213 H213 0.93(3) . ? C215 H15D 1.04(4) . ? C215 H15E 1.04(4) . ? C215 H15F 0.87(4) . ? 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 C106 N101 C102 119.8(2) . . ? C106 N101 C114 119.5(2) . . ? C102 N101 C114 120.65(19) . . ? O102 C102 O102 0.0(3) 1 . ? O102 C102 C103 122.8(2) 1 . ? O102 C102 C103 122.8(2) . . ? O102 C102 N101 120.7(2) 1 . ? O102 C102 N101 120.7(2) . . ? C103 C102 N101 116.5(2) . . ? O102 O102 C102 0(10) 1 . ? C104 C103 C102 123.8(2) . . ? C104 C103 Cl1 119.5(2) . . ? C102 C103 Cl1 116.71(19) . . ? O104 C104 C103 125.5(3) . . ? O104 C104 C105 117.0(2) . . ? C103 C104 C105 117.4(2) . . ? C104 O104 H104 113(3) . . ? C106 C105 C104 122.2(2) . . ? C106 C105 Cl2 120.6(2) . . ? C104 C105 Cl2 117.19(19) . . ? C105 C106 N101 119.9(2) . . ? C105 C106 C107 121.5(2) . . ? N101 C106 C107 118.5(2) . . ? C108 C107 C106 122.3(2) . . ? C108 C107 H107 119(2) . . ? C106 C107 H107 119(2) . . ? C107 C108 C109 120.5(3) . . ? C107 C108 H108 125.4(18) . . ? C109 C108 H108 114.1(18) . . ? C110 C109 C114 119.6(2) . . ? C110 C109 C108 120.6(2) . . ? C114 C109 C108 119.7(2) . . ? C111 C110 C109 122.5(2) . . ? C111 C110 H110 123(2) . . ? C109 C110 H110 115(2) . . ? C110 C111 C112 117.0(2) . . ? C110 C111 C115 121.7(3) . . ? C112 C111 C115 121.3(3) . . ? C113 C112 C111 122.6(2) . . ? C113 C112 H112 120(2) . . ? C111 C112 H112 117(2) . . ? C112 C113 C114 120.6(2) . . ? C112 C113 H113 121(2) . . ? C114 C113 H113 119(2) . . ? C113 C114 C109 117.6(2) . . ? C113 C114 N101 123.6(2) . . ? C109 C114 N101 118.7(2) . . ? C111 C115 H15A 108(2) . . ? C111 C115 H15B 110(3) . . ? H15A C115 H15B 106(4) . . ? C111 C115 H15C 111(2) . . ? H15A C115 H15C 107(3) . . ? H15B C115 H15C 114(4) . . ? C206 N201 C202 119.8(2) . . ? C206 N201 C214 119.65(19) . . ? C202 N201 C214 120.49(19) . . ? O202 C202 N201 121.2(2) . . ? O202 C202 C203 122.4(2) . . ? N201 C202 C203 116.3(2) . . ? C204 C203 C202 124.1(2) . . ? C204 C203 Cl3 119.25(19) . . ? C202 C203 Cl3 116.58(18) . . ? O204 C204 C203 125.1(2) . . ? O204 C204 C205 117.8(2) . . ? C203 C204 C205 117.1(2) . . ? C204 O204 H204 112(4) . . ? C206 C205 C204 122.4(2) . . ? C206 C205 Cl4 120.0(2) . . ? C204 C205 Cl4 117.54(19) . . ? C205 C206 N201 120.0(2) . . ? C205 C206 C207 120.9(2) . . ? N201 C206 C207 119.1(2) . . ? C208 C207 C206 121.6(3) . . ? C208 C207 H207 120.3(18) . . ? C206 C207 H207 118.1(18) . . ? C207 C208 C209 121.4(2) . . ? C207 C208 H208 117.5(17) . . ? C209 C208 H208 121.1(17) . . ? C210 C209 C214 119.7(2) . . ? C210 C209 C208 120.8(2) . . ? C214 C209 C208 119.5(2) . . ? C211 C210 C209 123.2(3) . . ? C211 C210 H210 118.4(18) . . ? C209 C210 H210 118.3(18) . . ? C210 C211 C212 116.4(2) . . ? C210 C211 C215 122.5(3) . . ? C212 C211 C215 121.1(3) . . ? C213 C212 C211 122.7(3) . . ? C213 C212 H212 117.9(19) . . ? C211 C212 H212 119.4(19) . . ? C212 C213 C214 120.5(3) . . ? C212 C213 H213 113.8(18) . . ? C214 C213 H213 125.7(18) . . ? C213 C214 C209 117.5(2) . . ? C213 C214 N201 123.9(2) . . ? C209 C214 N201 118.6(2) . . ? C211 C215 H15D 105(2) . . ? C211 C215 H15E 112(2) . . ? H15D C215 H15E 99(3) . . ? C211 C215 H15F 108(3) . . ? H15D C215 H15F 115(4) . . ? H15E C215 H15F 116(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C106 N101 C102 O102 173.5(2) . . . 1 ? C114 N101 C102 O102 -5.1(4) . . . 1 ? C106 N101 C102 O102 173.5(2) . . . . ? C114 N101 C102 O102 -5.1(4) . . . . ? C106 N101 C102 C103 -6.0(3) . . . . ? C114 N101 C102 C103 175.5(2) . . . . ? C103 C102 O102 O102 0.00(8) . . . 1 ? N101 C102 O102 O102 0.0(2) . . . 1 ? O102 C102 C103 C104 -177.2(3) 1 . . . ? O102 C102 C103 C104 -177.2(3) . . . . ? N101 C102 C103 C104 2.2(4) . . . . ? O102 C102 C103 Cl1 2.3(4) 1 . . . ? O102 C102 C103 Cl1 2.3(4) . . . . ? N101 C102 C103 Cl1 -178.27(18) . . . . ? C102 C103 C104 O104 179.5(3) . . . . ? Cl1 C103 C104 O104 0.0(4) . . . . ? C102 C103 C104 C105 1.1(4) . . . . ? Cl1 C103 C104 C105 -178.4(2) . . . . ? O104 C104 C105 C106 -179.2(2) . . . . ? C103 C104 C105 C106 -0.7(4) . . . . ? O104 C104 C105 Cl2 -1.5(3) . . . . ? C103 C104 C105 Cl2 177.1(2) . . . . ? C104 C105 C106 N101 -3.1(4) . . . . ? Cl2 C105 C106 N101 179.23(17) . . . . ? C104 C105 C106 C107 173.9(3) . . . . ? Cl2 C105 C106 C107 -3.7(4) . . . . ? C102 N101 C106 C105 6.5(3) . . . . ? C114 N101 C106 C105 -174.9(2) . . . . ? C102 N101 C106 C107 -170.6(2) . . . . ? C114 N101 C106 C107 8.0(3) . . . . ? C105 C106 C107 C108 -177.8(3) . . . . ? N101 C106 C107 C108 -0.7(4) . . . . ? C106 C107 C108 C109 -4.8(5) . . . . ? C107 C108 C109 C110 -173.3(3) . . . . ? C107 C108 C109 C114 3.0(4) . . . . ? C114 C109 C110 C111 -0.5(4) . . . . ? C108 C109 C110 C111 175.8(3) . . . . ? C109 C110 C111 C112 -1.1(4) . . . . ? C109 C110 C111 C115 178.6(3) . . . . ? C110 C111 C112 C113 0.7(4) . . . . ? C115 C111 C112 C113 -179.1(3) . . . . ? C111 C112 C113 C114 1.4(4) . . . . ? C112 C113 C114 C109 -3.0(4) . . . . ? C112 C113 C114 N101 179.1(2) . . . . ? C110 C109 C114 C113 2.5(4) . . . . ? C108 C109 C114 C113 -173.8(3) . . . . ? C110 C109 C114 N101 -179.4(2) . . . . ? C108 C109 C114 N101 4.2(4) . . . . ? C106 N101 C114 C113 168.3(2) . . . . ? C102 N101 C114 C113 -13.2(3) . . . . ? C106 N101 C114 C109 -9.7(3) . . . . ? C102 N101 C114 C109 168.9(2) . . . . ? C206 N201 C202 O202 -174.0(2) . . . . ? C214 N201 C202 O202 4.2(4) . . . . ? C206 N201 C202 C203 5.3(3) . . . . ? C214 N201 C202 C203 -176.6(2) . . . . ? O202 C202 C203 C204 177.5(3) . . . . ? N201 C202 C203 C204 -1.7(4) . . . . ? O202 C202 C203 Cl3 0.9(4) . . . . ? N201 C202 C203 Cl3 -178.30(18) . . . . ? C202 C203 C204 O204 -179.4(3) . . . . ? Cl3 C203 C204 O204 -2.9(4) . . . . ? C202 C203 C204 C205 -1.9(4) . . . . ? Cl3 C203 C204 C205 174.5(2) . . . . ? O204 C204 C205 C206 179.8(2) . . . . ? C203 C204 C205 C206 2.2(4) . . . . ? O204 C204 C205 Cl4 -0.5(3) . . . . ? C203 C204 C205 Cl4 -178.1(2) . . . . ? C204 C205 C206 N201 1.3(4) . . . . ? Cl4 C205 C206 N201 -178.38(19) . . . . ? C204 C205 C206 C207 -177.2(3) . . . . ? Cl4 C205 C206 C207 3.1(4) . . . . ? C202 N201 C206 C205 -5.2(3) . . . . ? C214 N201 C206 C205 176.7(2) . . . . ? C202 N201 C206 C207 173.3(2) . . . . ? C214 N201 C206 C207 -4.8(3) . . . . ? C205 C206 C207 C208 179.5(3) . . . . ? N201 C206 C207 C208 1.0(4) . . . . ? C206 C207 C208 C209 2.4(5) . . . . ? C207 C208 C209 C210 177.6(3) . . . . ? C207 C208 C209 C214 -1.9(4) . . . . ? C214 C209 C210 C211 0.1(4) . . . . ? C208 C209 C210 C211 -179.5(3) . . . . ? C209 C210 C211 C212 2.0(4) . . . . ? C209 C210 C211 C215 -178.0(3) . . . . ? C210 C211 C212 C213 -2.1(4) . . . . ? C215 C211 C212 C213 178.0(3) . . . . ? C211 C212 C213 C214 0.0(4) . . . . ? C212 C213 C214 C209 2.1(4) . . . . ? C212 C213 C214 N201 -178.6(2) . . . . ? C210 C209 C214 C213 -2.2(4) . . . . ? C208 C209 C214 C213 177.4(2) . . . . ? C210 C209 C214 N201 178.5(2) . . . . ? C208 C209 C214 N201 -1.9(4) . . . . ? C206 N201 C214 C213 -174.0(2) . . . . ? C202 N201 C214 C213 7.8(4) . . . . ? C206 N201 C214 C209 5.2(3) . . . . ? C202 N201 C214 C209 -172.9(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.392 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.067 #======================================================================= # 1. SUBMISSION DETAILS _publ_requested_journal 'J. Chem. Soc. Perkin Trans. 1' _publ_requested_coeditor_name ? _publ_contact_author ; Prof. Peter Luger Institut f\"ur Chemie/Kristallographie Freie Universit\"at Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; _publ_contact_author_phone '0049-030-83853411' _publ_contact_author_fax '0049-030-83853464' _publ_contact_author_email 'luger@chemie.fu-berlin.de' _publ_contact_letter ; This material is intended solely for deposition ; #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; A Noval Annelation to Quinolines and Isoquinolines Under Friedel-Crafts Conditions: A One-Step Synthesis of Functionalized Benzoquinolizines ; loop_ _publ_author_name _publ_author_address 'Luger, Peter' ; Institut f\"ur Chemie/Kristallographie Freie Universit\"at Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; 'Weber, Manuela' ; Institut f\"ur Chemie/Kristallographie Freie Universit\"at Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; 'Mahato, Shashi B.' ; Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road Jadavpur Calcutta-700 032 India ; 'Garai, Subhadra' : Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road Jadavpur Calcutta-700 032 India ; #======================================================================= # 4. TEXT _publ_section_abstract ; ... and following paragraphs: see the published paper. ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #end of data data_nqn1_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Cl2 N O2' _chemical_formula_sum 'C13 H7 Cl2 N O2' _chemical_formula_weight 280.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0170 0.0090 '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' 'Cl' 'Cl' 0.3480 0.7020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0470 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0290 0.0180 '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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.539(5) _cell_length_b 16.57(1) _cell_length_c 12.285(9) _cell_angle_alpha 90.00(7) _cell_angle_beta 96.54(7) _cell_angle_gamma 90.00(7) _cell_volume 1120.2(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 21 _cell_measurement_theta_max 53 _exptl_crystal_description plate _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 5.154 _exptl_absorpt_correction_type 'gaussian' _exptl_absorpt_correction_T_min 0.429 _exptl_absorpt_correction_T_max 0.814 _exptl_absorpt_process_details '(Hall, 1982)' _exptl_special_details ; Ni filter used ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator no _diffrn_measurement_device_type ; Stoe four circle diffractometer, microVAX controlled ; _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 3 _diffrn_reflns_number 1855 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0831 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.50 _diffrn_reflns_theta_max 60.17 _reflns_number_total 1668 _reflns_number_gt 935 _reflns_threshold_expression >4sigma(Fo) _computing_data_collection 'STOE software' _computing_cell_refinement 'STOE software' _computing_data_reduction 'Stoe-routine REDUC' _computing_structure_solution 'SIR92 (Altomare, 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; SCHAKAL88 (Keller, 1988), ORTEP (Stewart 1986) ; _computing_publication_material ; SHELXL-93_ACTA (Sheldrick, 1993) ; _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^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.0001(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1668 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1698 _refine_ls_R_factor_gt 0.0960 _refine_ls_wR_factor_ref 0.2736 _refine_ls_wR_factor_gt 0.2429 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.2560(13) 0.1254(4) 0.7334(5) 0.0598(18) Uani 1 1 d . . . C2 C 0.1604(13) 0.1932(4) 0.6764(5) 0.0599(18) Uani 1 1 d . . . C3 C -0.0213(12) 0.2411(4) 0.7128(5) 0.0576(18) Uani 1 1 d . . . O3 O -0.1194(9) 0.3043(3) 0.6578(4) 0.0704(15) Uani 1 1 d . . . H3 H -0.131(14) 0.316(5) 0.561(7) 0.10(2) Uiso 1 1 d . . . C4 C -0.1091(14) 0.2225(5) 0.8110(6) 0.068(2) Uani 1 1 d . . . C5 C -0.0243(15) 0.1546(5) 0.8722(5) 0.074(2) Uani 1 1 d . . . O5 O -0.0981(12) 0.1339(4) 0.9613(4) 0.096(2) Uani 1 1 d . . . N6 N 0.1560(12) 0.1075(4) 0.8304(4) 0.0691(18) Uani 1 1 d . . . C7 C 0.2200(17) 0.0371(6) 0.8892(7) 0.085(2) Uani 1 1 d . . . H7 H 0.1463 0.0262 0.9519 0.102 Uiso 1 1 calc R . . C8 C 0.3793(19) -0.0139(6) 0.8594(7) 0.094(3) Uani 1 1 d . . . H8 H 0.4120 -0.0609 0.8999 0.113 Uiso 1 1 calc R . . C9 C 0.5032(15) 0.0007(5) 0.7671(7) 0.083(2) Uani 1 1 d . . . C10 C 0.692(2) -0.0501(6) 0.7412(10) 0.110(4) Uani 1 1 d . . . H10 H 0.7310 -0.0951 0.7849 0.132 Uiso 1 1 calc R . . C11 C 0.8175(19) -0.0363(6) 0.6564(9) 0.100(3) Uani 1 1 d . . . H11 H 0.9365 -0.0722 0.6391 0.119 Uiso 1 1 calc R . . C12 C 0.7652(17) 0.0334(6) 0.5945(8) 0.098(3) Uani 1 1 d . . . H12 H 0.8519 0.0444 0.5357 0.118 Uiso 1 1 calc R . . C13 C 0.5902(15) 0.0853(5) 0.6187(6) 0.079(2) Uani 1 1 d . . . H13 H 0.5633 0.1318 0.5765 0.095 Uiso 1 1 calc R . . C14 C 0.4478(13) 0.0723(4) 0.7041(5) 0.0637(19) Uani 1 1 d . . . Cl1 Cl -0.3282(4) 0.28017(14) 0.85872(16) 0.0914(9) Uani 1 1 d . . . Cl2 Cl 0.2565(5) 0.22551(15) 0.55525(16) 0.1019(10) Uani 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 C1 0.072(5) 0.060(4) 0.047(3) -0.004(3) 0.000(3) -0.019(4) C2 0.068(5) 0.066(4) 0.046(4) -0.005(3) 0.009(3) -0.015(4) C3 0.064(4) 0.067(4) 0.042(3) -0.008(3) 0.006(3) -0.014(4) O3 0.088(4) 0.080(3) 0.047(3) 0.000(2) 0.022(2) 0.010(3) C4 0.080(5) 0.080(5) 0.050(4) -0.020(4) 0.027(3) -0.025(4) C5 0.102(6) 0.079(5) 0.044(4) -0.012(4) 0.017(4) -0.040(5) O5 0.151(5) 0.098(4) 0.046(3) -0.005(3) 0.040(3) -0.050(4) N6 0.100(5) 0.072(4) 0.036(3) 0.004(3) 0.012(3) -0.021(3) C7 0.101(7) 0.080(6) 0.071(5) 0.023(4) 0.005(4) -0.018(5) C8 0.111(7) 0.083(6) 0.084(6) 0.034(5) -0.009(5) -0.022(6) C9 0.083(6) 0.077(6) 0.082(5) 0.014(4) -0.016(4) -0.016(5) C10 0.107(8) 0.077(6) 0.138(10) 0.014(6) -0.026(7) 0.016(6) C11 0.093(7) 0.091(7) 0.112(8) -0.018(6) -0.002(6) 0.014(6) C12 0.094(7) 0.093(6) 0.109(7) -0.017(5) 0.015(5) 0.026(6) C13 0.093(6) 0.068(5) 0.077(5) -0.001(4) 0.014(4) 0.013(5) C14 0.077(5) 0.068(4) 0.044(3) 0.000(3) -0.004(3) -0.012(4) Cl1 0.0969(17) 0.1164(19) 0.0677(13) -0.0222(11) 0.0385(11) -0.0125(13) Cl2 0.129(2) 0.1179(18) 0.0684(13) 0.0412(11) 0.0537(12) 0.0526(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.396(9) . ? C1 N6 1.402(9) . ? C1 C14 1.455(10) . ? C2 C3 1.395(10) . ? C2 Cl2 1.722(7) . ? C3 O3 1.328(8) . ? C3 C4 1.386(10) . ? O3 H3 1.19(8) . ? C4 C5 1.403(11) . ? C4 Cl1 1.701(8) . ? C5 O5 1.260(8) . ? C5 N6 1.411(11) . ? N6 C7 1.396(10) . ? C7 C8 1.304(13) . ? C7 H7 0.9300 . ? C8 C9 1.412(13) . ? C8 H8 0.9300 . ? C9 C10 1.406(14) . ? C9 C14 1.431(10) . ? C10 C11 1.337(15) . ? C10 H10 0.9300 . ? C11 C12 1.395(14) . ? C11 H11 0.9300 . ? C12 C13 1.354(11) . ? C12 H12 0.9300 . ? C13 C14 1.400(11) . ? C13 H13 0.9300 . ? 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 C1 N6 115.7(7) . . ? C2 C1 C14 127.5(7) . . ? N6 C1 C14 116.8(6) . . ? C1 C2 C3 122.9(6) . . ? C1 C2 Cl2 123.2(6) . . ? C3 C2 Cl2 113.9(5) . . ? O3 C3 C4 117.1(7) . . ? O3 C3 C2 123.6(6) . . ? C4 C3 C2 119.3(7) . . ? C3 O3 H3 127(4) . . ? C3 C4 C5 121.1(7) . . ? C3 C4 Cl1 120.6(6) . . ? C5 C4 Cl1 118.3(6) . . ? O5 C5 C4 124.3(8) . . ? O5 C5 N6 118.6(8) . . ? C4 C5 N6 117.2(6) . . ? C7 N6 C1 121.0(7) . . ? C7 N6 C5 115.0(7) . . ? C1 N6 C5 123.8(6) . . ? C8 C7 N6 122.4(9) . . ? C8 C7 H7 118.8 . . ? N6 C7 H7 118.8 . . ? C7 C8 C9 121.4(8) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 121.4(9) . . ? C10 C9 C14 119.6(9) . . ? C8 C9 C14 118.8(9) . . ? C11 C10 C9 122.7(10) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C10 C11 C12 118.2(10) . . ? C10 C11 H11 120.9 . . ? C12 C11 H11 120.9 . . ? C13 C12 C11 121.0(10) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 123.1(8) . . ? C12 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C13 C14 C9 115.3(8) . . ? C13 C14 C1 125.6(7) . . ? C9 C14 C1 119.1(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N6 C1 C2 C3 0.6(10) . . . . ? C14 C1 C2 C3 -178.7(6) . . . . ? N6 C1 C2 Cl2 -179.7(5) . . . . ? C14 C1 C2 Cl2 1.0(10) . . . . ? C1 C2 C3 O3 -177.8(6) . . . . ? Cl2 C2 C3 O3 2.5(9) . . . . ? C1 C2 C3 C4 1.4(10) . . . . ? Cl2 C2 C3 C4 -178.3(5) . . . . ? O3 C3 C4 C5 177.0(6) . . . . ? C2 C3 C4 C5 -2.2(10) . . . . ? O3 C3 C4 Cl1 -1.4(9) . . . . ? C2 C3 C4 Cl1 179.3(5) . . . . ? C3 C4 C5 O5 -179.3(7) . . . . ? Cl1 C4 C5 O5 -0.8(10) . . . . ? C3 C4 C5 N6 1.0(10) . . . . ? Cl1 C4 C5 N6 179.5(5) . . . . ? C2 C1 N6 C7 174.0(6) . . . . ? C14 C1 N6 C7 -6.7(9) . . . . ? C2 C1 N6 C5 -1.9(10) . . . . ? C14 C1 N6 C5 177.5(6) . . . . ? O5 C5 N6 C7 5.3(10) . . . . ? C4 C5 N6 C7 -174.9(6) . . . . ? O5 C5 N6 C1 -178.6(6) . . . . ? C4 C5 N6 C1 1.1(10) . . . . ? C1 N6 C7 C8 2.0(12) . . . . ? C5 N6 C7 C8 178.2(8) . . . . ? N6 C7 C8 C9 2.1(14) . . . . ? C7 C8 C9 C10 173.6(9) . . . . ? C7 C8 C9 C14 -1.3(13) . . . . ? C8 C9 C10 C11 -177.8(10) . . . . ? C14 C9 C10 C11 -3.0(14) . . . . ? C9 C10 C11 C12 3.0(16) . . . . ? C10 C11 C12 C13 -0.7(15) . . . . ? C11 C12 C13 C14 -1.5(13) . . . . ? C12 C13 C14 C9 1.5(11) . . . . ? C12 C13 C14 C1 -179.4(7) . . . . ? C10 C9 C14 C13 0.7(10) . . . . ? C8 C9 C14 C13 175.7(7) . . . . ? C10 C9 C14 C1 -178.5(7) . . . . ? C8 C9 C14 C1 -3.5(10) . . . . ? C2 C1 C14 C13 7.5(11) . . . . ? N6 C1 C14 C13 -171.8(7) . . . . ? C2 C1 C14 C9 -173.4(6) . . . . ? N6 C1 C14 C9 7.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 60.17 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.586 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.131 #======================================================================= # 1. SUBMISSION DETAILS _publ_requested_journal 'J. Chem. Soc. Perkin Trans. 1' _publ_requested_coeditor_name ? _publ_contact_author ; Prof. Peter Luger Institut f\"ur Chemie/Kristallographie Freie Universit\"at Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; _publ_contact_author_phone '0049-030-83853411' _publ_contact_author_fax '0049-030-83853464' _publ_contact_author_email 'luger@chemie.fu-berlin.de' _publ_contact_letter ; This material is intended solely for deposition ; #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; A Noval Annelation to Quinolines and Isoquinolines Under Friedel-Crafts Conditions: A One-Step Synthesis of Functionalized Benzoquinolizines ; loop_ _publ_author_name _publ_author_address 'Luger, Peter' ; Institut f\"ur Chemie/Kristallographie Freie Universit\"at Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; 'Weber, Manuela' ; Institut f\"ur Chemie/Kristallographie Freie Universit\"at Fachbereich Biologie, Chemie, Pharmazie Takustr. 6 14195 Berlin Germany ; 'Mahato, Shashi B.' ; Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road Jadavpur Calcutta-700 032 India ; 'Garai, Subhadra' : Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road Jadavpur Calcutta-700 032 India ; #======================================================================= # 4. TEXT _publ_section_abstract ; ... and following paragraphs: see the published paper. ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #end of data