data_2014725 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2005 _journal_volume 61 _journal_page_first o1 _journal_page_last o3 _publ_section_title ; 4,5,6,8,9-Pentachloropyrimido[1,2a][1,8]naphthyridin-10-one ; loop_ _publ_author_name 'Bortoluzzi, Adailton J.' 'Joussef, Antonio C.' 'Silva, Luiz E.' 'Rebelo, Ricardo A.' _chemical_formula_moiety 'C11 H2 Cl5 N3 O' _chemical_formula_sum 'C11 H2 Cl5 N3 O' _chemical_formula_iupac 'C11 H2 Cl5 N3 O' _chemical_formula_weight 369.41 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 16.453(3) _cell_length_b 7.1730(10) _cell_length_c 22.368(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.26(2) _cell_angle_gamma 90.00 _cell_volume 2520.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _exptl_crystal_density_diffrn 1.947 _diffrn_ambient_temperature 193(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1A 0.75977(17) 0.7134(4) 0.56516(13) 0.0176(5) Uani d . 1 . . C C2 0.90251(18) 0.6646(4) 0.60516(14) 0.0245(6) Uani d . 1 . . C H2 0.9524 0.6660 0.6400 0.029 Uiso calc R 1 . . H C3 0.91034(18) 0.6200(4) 0.54716(14) 0.0242(6) Uani d . 1 . . C H3 0.9645 0.5924 0.5423 0.029 Uiso calc R 1 . . H C4 0.83810(18) 0.6160(4) 0.49616(13) 0.0211(6) Uani d . 1 . . C C4A 0.75803(17) 0.6707(4) 0.50275(12) 0.0179(6) Uani d . 1 . . C C5 0.67701(18) 0.6784(4) 0.45435(12) 0.0205(6) Uani d . 1 . . C C6 0.60410(17) 0.7005(4) 0.47013(12) 0.0196(6) Uani d . 1 . . C C6A 0.60449(17) 0.7389(4) 0.53376(13) 0.0196(6) Uani d . 1 . . C C8 0.53175(18) 0.8082(4) 0.60275(14) 0.0234(6) Uani d . 1 . . C C9 0.60317(18) 0.8618(4) 0.64815(13) 0.0218(6) Uani d . 1 . . C C10 0.68507(17) 0.8530(4) 0.63736(12) 0.0197(6) Uani d . 1 . . C N1 0.82829(14) 0.7057(3) 0.61462(11) 0.0215(5) Uani d . 1 . . N N7 0.53147(15) 0.7565(4) 0.54511(11) 0.0240(5) Uani d . 1 . . N N10A 0.68302(14) 0.7648(3) 0.57859(10) 0.0179(5) Uani d . 1 . . N O1 0.74979(12) 0.9158(3) 0.67339(9) 0.0258(5) Uani d . 1 . . O Cl1 0.85216(5) 0.53137(12) 0.42775(3) 0.0303(2) Uani d . 1 . . Cl Cl2 0.66924(5) 0.66533(13) 0.37632(3) 0.0329(2) Uani d . 1 . . Cl Cl3 0.50657(4) 0.69676(11) 0.41527(3) 0.02813(19) Uani d . 1 . . Cl Cl4 0.43414(5) 0.81213(14) 0.61592(4) 0.0369(2) Uani d . 1 . . Cl Cl5 0.60123(5) 0.95300(11) 0.71853(3) 0.02978(19) Uani d . 1 . . Cl C11A 0.07727(17) 0.7403(4) 0.30104(12) 0.0177(5) Uani d . 1 . . C C12 -0.06641(18) 0.7132(4) 0.26181(13) 0.0230(6) Uani d . 1 . . C H12 -0.1150 0.6736 0.2293 0.028 Uiso calc R 1 . . H C13 -0.07854(17) 0.7903(4) 0.31505(13) 0.0211(6) Uani d . 1 . . C H13 -0.1344 0.8114 0.3177 0.025 Uiso calc R 1 . . H C14 -0.00813(18) 0.8365(4) 0.36449(12) 0.0193(6) Uani d . 1 . . C C14A 0.07479(17) 0.8033(4) 0.36041(12) 0.0177(6) Uani d . 1 . . C C15 0.15543(17) 0.8095(4) 0.41023(12) 0.0198(6) Uani d . 1 . . C C16 0.22768(17) 0.7500(4) 0.39953(12) 0.0191(6) Uani d . 1 . . C C16A 0.23084(17) 0.6974(4) 0.33785(13) 0.0179(6) Uani d . 1 . . C C18 0.30526(17) 0.6132(4) 0.27137(13) 0.0208(6) Uani d . 1 . . C C19 0.23984(18) 0.6529(4) 0.21984(13) 0.0207(6) Uani d . 1 . . C C20 0.16181(17) 0.7304(4) 0.22555(12) 0.0198(6) Uani d . 1 . . C N11 0.01005(15) 0.6918(4) 0.25380(11) 0.0209(5) Uani d . 1 . . N N17 0.30359(15) 0.6425(4) 0.33061(11) 0.0223(5) Uani d . 1 . . N N20A 0.15679(14) 0.7166(3) 0.28922(10) 0.0181(5) Uani d . 1 . . N O2 0.10672(12) 0.8050(3) 0.18439(9) 0.0271(5) Uani d . 1 . . O Cl6 -0.02940(5) 0.93633(13) 0.42822(3) 0.0336(2) Uani d . 1 . . Cl Cl7 0.16148(4) 0.88150(11) 0.48464(3) 0.02616(18) Uani d . 1 . . Cl Cl8 0.32331(4) 0.74718(11) 0.45735(3) 0.02521(18) Uani d . 1 . . Cl Cl9 0.40059(4) 0.53309(12) 0.26428(3) 0.0308(2) Uani d . 1 . . Cl Cl10 0.24718(5) 0.63364(12) 0.14515(3) 0.0305(2) Uani d . 1 . . Cl loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1A 0.0154(13) 0.0173(13) 0.0194(13) 0.0000(10) 0.0042(11) 0.0017(11) C2 0.0136(13) 0.0326(17) 0.0240(15) -0.0001(12) 0.0004(11) 0.0006(12) C3 0.0152(13) 0.0316(16) 0.0262(15) -0.0012(12) 0.0070(11) -0.0007(13) C4 0.0217(14) 0.0242(14) 0.0196(14) -0.0024(12) 0.0095(11) -0.0011(12) C4A 0.0171(13) 0.0186(13) 0.0170(13) -0.0025(11) 0.0034(11) 0.0010(10) C5 0.0221(14) 0.0242(14) 0.0139(13) -0.0017(12) 0.0030(11) 0.0016(11) C6 0.0170(13) 0.0235(14) 0.0150(13) -0.0015(11) -0.0004(11) 0.0015(11) C6A 0.0148(13) 0.0228(14) 0.0185(14) -0.0005(11) 0.0008(11) 0.0023(11) C8 0.0165(14) 0.0300(16) 0.0239(15) 0.0005(12) 0.0063(11) -0.0002(12) C9 0.0201(14) 0.0291(15) 0.0163(13) 0.0011(12) 0.0057(11) 0.0000(12) C10 0.0196(14) 0.0223(14) 0.0160(13) 0.0011(11) 0.0035(11) 0.0025(11) N1 0.0154(11) 0.0287(13) 0.0178(12) 0.0004(10) 0.0009(9) -0.0011(10) N7 0.0150(11) 0.0344(14) 0.0205(12) -0.0005(10) 0.0023(9) -0.0009(11) N10A 0.0136(11) 0.0242(12) 0.0144(11) -0.0004(9) 0.0018(9) 0.0015(9) O1 0.0171(10) 0.0345(12) 0.0230(11) -0.0005(9) 0.0015(8) -0.0074(9) Cl1 0.0274(4) 0.0440(5) 0.0226(4) 0.0000(3) 0.0123(3) -0.0066(3) Cl2 0.0282(4) 0.0561(5) 0.0136(3) -0.0004(4) 0.0050(3) -0.0004(3) Cl3 0.0175(3) 0.0431(4) 0.0184(3) 0.0006(3) -0.0031(3) -0.0009(3) Cl4 0.0181(4) 0.0617(6) 0.0335(4) -0.0039(3) 0.0118(3) -0.0096(4) Cl5 0.0284(4) 0.0405(4) 0.0224(4) -0.0019(3) 0.0106(3) -0.0081(3) C11A 0.0160(13) 0.0226(14) 0.0141(13) -0.0005(11) 0.0038(10) 0.0009(11) C12 0.0163(13) 0.0330(16) 0.0165(13) -0.0022(12) -0.0001(11) 0.0019(12) C13 0.0147(13) 0.0266(15) 0.0220(14) 0.0005(11) 0.0056(11) 0.0025(12) C14 0.0209(14) 0.0225(14) 0.0159(13) 0.0016(11) 0.0075(11) 0.0010(11) C14A 0.0153(13) 0.0212(14) 0.0156(13) -0.0015(11) 0.0033(10) 0.0013(11) C15 0.0208(14) 0.0259(15) 0.0112(13) -0.0036(11) 0.0024(11) 0.0011(11) C16 0.0151(13) 0.0242(14) 0.0144(13) -0.0011(11) -0.0011(10) 0.0026(11) C16A 0.0150(13) 0.0198(13) 0.0170(13) -0.0009(11) 0.0016(10) 0.0035(11) C18 0.0152(13) 0.0258(15) 0.0218(14) 0.0016(11) 0.0059(11) 0.0000(12) C19 0.0219(14) 0.0233(15) 0.0173(14) -0.0006(11) 0.0067(11) -0.0004(11) C20 0.0175(13) 0.0257(15) 0.0160(14) -0.0023(11) 0.0046(11) 0.0012(11) N11 0.0163(11) 0.0299(13) 0.0146(11) -0.0008(10) 0.0015(9) 0.0015(10) N17 0.0157(11) 0.0309(13) 0.0190(12) 0.0009(10) 0.0031(9) 0.0017(10) N20A 0.0145(11) 0.0263(12) 0.0121(11) 0.0015(9) 0.0018(9) 0.0012(9) O2 0.0179(10) 0.0468(13) 0.0154(10) 0.0059(9) 0.0031(8) 0.0083(9) Cl6 0.0244(4) 0.0543(5) 0.0250(4) -0.0026(3) 0.0117(3) -0.0145(3) Cl7 0.0270(4) 0.0366(4) 0.0130(3) -0.0005(3) 0.0031(3) -0.0047(3) Cl8 0.0167(3) 0.0372(4) 0.0161(3) -0.0011(3) -0.0037(3) 0.0012(3) Cl9 0.0207(4) 0.0441(5) 0.0282(4) 0.0090(3) 0.0083(3) 0.0023(3) Cl10 0.0232(4) 0.0531(5) 0.0170(3) 0.0056(3) 0.0085(3) 0.0005(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1A N1 . 1.326(4) ? C1A C4A . 1.421(4) ? C1A N10A . 1.430(4) y C2 N1 . 1.333(4) ? C2 C3 . 1.379(4) ? C2 H2 . 0.9500 ? C3 C4 . 1.382(4) ? C3 H3 . 0.9500 ? C4 C4A . 1.423(4) ? C4 Cl1 . 1.724(3) ? C4A C5 . 1.448(4) ? C5 C6 . 1.357(4) ? C5 Cl2 . 1.714(3) ? C6 C6A . 1.448(4) ? C6 Cl3 . 1.707(3) ? C6A N7 . 1.306(4) y C6A N10A . 1.393(3) y C8 N7 . 1.340(4) y C8 C9 . 1.361(4) ? C8 Cl4 . 1.717(3) ? C9 C10 . 1.439(4) ? C9 Cl5 . 1.714(3) ? C10 O1 . 1.215(3) ? C10 N10A . 1.450(4) y C11A N11 . 1.329(4) ? C11A C14A . 1.415(4) ? C11A N20A . 1.420(3) y C12 N11 . 1.331(4) ? C12 C13 . 1.380(4) ? C12 H12 . 0.9500 ? C13 C14 . 1.384(4) ? C13 H13 . 0.9500 ? C14 C14A . 1.414(4) ? C14 Cl6 . 1.721(3) ? C14A C15 . 1.458(4) ? C15 C16 . 1.350(4) ? C15 Cl7 . 1.717(3) ? C16 C16A . 1.446(4) ? C16 Cl8 . 1.715(3) ? C16A N17 . 1.315(4) y C16A N20A . 1.378(3) y C18 N17 . 1.350(4) y C18 C19 . 1.354(4) ? C18 Cl9 . 1.721(3) ? C19 C20 . 1.439(4) ? C19 Cl10 . 1.716(3) ? C20 O2 . 1.209(3) ? C20 N20A . 1.454(3) ?