data_2200796 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o937 _journal_page_last o938 _publ_section_title ; 11-Chloro-5H-6,7-dihydrobenzothiazolo[2,3-b]benzo[h]quinazoline ; loop_ _publ_author_name 'Low, John Nicolson' 'Cobo, Justo' 'Nogueras, Manuel' "S\'anchez, Adolfo" 'Quiroga, Jairo' "Hern\'andez, Pedro" _chemical_formula_moiety 'C18 H13 Cl1 N2 S1' _chemical_formula_sum 'C18 H13 Cl1 N2 S1' _chemical_formula_iupac 'C18 H13 Cl1 N2 S1' _chemical_formula_weight 324.82 _chemical_melting_point 452 _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 7.2637(3) _cell_length_b 14.4294(5) _cell_length_c 15.1081(5) _cell_angle_alpha 70.368(3) _cell_angle_beta 78.550(2) _cell_angle_gamma 89.0800(14) _cell_volume 1459.56(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120.0(10) _exptl_crystal_density_diffrn 1.478 _diffrn_ambient_temperature 120.0(10) 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 C11 .9497(3) .13006(13) .66763(12) .0210(4) Uani d . 1 . . C C12 .8722(3) .12940(13) .75932(13) .0235(4) Uani d . 1 . . C C13 .6797(3) .13427(14) .78764(12) .0241(4) Uani d . 1 . . C Cl13 .58735(8) .13428(4) .90268(3) .03721(16) Uani d . 1 . . Cl C14 .5574(3) .13836(13) .72597(12) .0224(4) Uani d . 1 . . C C14A .6350(3) .13698(13) .63522(12) .0197(4) Uani d . 1 . . C C41A .8302(3) .13335(12) .60551(12) .0187(4) Uani d . 1 . . C S15 .51835(7) .13400(4) .54521(3) .02312(13) Uani d . 1 . . S C15A .7328(3) .12633(13) .46944(12) .0184(4) Uani d . 1 . . C N16 .7403(2) .11994(10) .38638(10) .0183(3) Uani d . 1 . . N C16A .9261(3) .11903(12) .33377(12) .0185(4) Uani d . 1 . . C C16B .9379(3) .10865(13) .23924(12) .0186(4) Uani d . 1 . . C C17 .7835(3) .07523(13) .21374(12) .0222(4) Uani d . 1 . . C C18 .7983(3) .06674(13) .12385(13) .0258(5) Uani d . 1 . . C C19 .9677(3) .09275(14) .05758(13) .0267(5) Uani d . 1 . . C C110 1.1225(3) .12491(14) .08292(13) .0259(5) Uani d . 1 . . C C10A 1.1115(3) .13234(13) .17268(13) .0205(4) Uani d . 1 . . C C111 1.2770(3) .16999(14) .20051(12) .0241(4) Uani d . 1 . . C C112 1.2746(3) .12503(14) .30755(13) .0220(4) Uani d . 1 . . C C113 1.0762(3) .13229(13) .46404(12) .0202(4) Uani d . 1 . . C C12A 1.0824(2) .12598(12) .36654(12) .0178(4) Uani d . 1 . . C N114 .8801(2) .12882(10) .51403(10) .0172(3) Uani d . 1 . . N C21 -.0308(3) .34448(13) -.15182(13) .0256(5) Uani d . 1 . . C C22 .0452(3) .34242(13) -.24258(13) .0277(5) Uani d . 1 . . C C23 .2377(3) .35663(14) -.27785(13) .0278(5) Uani d . 1 . . C Cl23 .32929(8) .35263(4) -.39189(3) .03944(16) Uani d . 1 . . Cl C24 .3596(3) .37532(13) -.22472(12) .0262(5) Uani d . 1 . . C C24A .2820(3) .38067(13) -.13546(12) .0226(4) Uani d . 1 . . C C42A .0888(3) .36402(13) -.09826(12) .0203(4) Uani d . 1 . . C S25 .39665(7) .40991(4) -.05581(3) .02585(14) Uani d . 1 . . S C25A .1820(3) .39806(13) .02719(12) .0188(4) Uani d . 1 . . C N26 .1730(2) .41199(10) .10724(10) .0192(3) Uani d . 1 . . N C26A -.0081(3) .39046(12) .16931(12) .0172(4) Uani d . 1 . . C C26B -.0152(3) .39420(13) .26629(12) .0179(4) Uani d . 1 . . C C27 .1472(3) .41247(13) .29521(12) .0219(4) Uani d . 1 . . C C28 .1393(3) .41513(14) .38667(13) .0257(4) Uani d . 1 . . C C29 -.0317(3) .39838(14) .45139(13) .0261(5) Uani d . 1 . . C C210 -.1935(3) .37956(13) .42335(13) .0240(4) Uani d . 1 . . C C21A -.1887(3) .37777(13) .33173(12) .0192(4) Uani d . 1 . . C C211 -.3683(3) .36587(14) .29940(12) .0223(4) Uani d . 1 . . C C212 -.3439(3) .32751(13) .21578(12) .0215(4) Uani d . 1 . . C C213 -.1543(3) .35037(13) .04946(12) .0201(4) Uani d . 1 . . C C22A -.1606(3) .36143(12) .14533(12) .0176(4) Uani d . 1 . . C N214 .0372(2) .37192(11) -.00789(10) .0188(3) Uani d . 1 . . N H11 1.0818 .1283 .6476 .025 Uiso calc R 1 . . H H12 .9517 .1256 .8032 .028 Uiso calc R 1 . . H H14 .4257 .1420 .7457 .027 Uiso calc R 1 . . H H17 .6669 .0581 .2585 .027 Uiso calc R 1 . . H H18 .6928 .0432 .1076 .031 Uiso calc R 1 . . H H19 .9777 .0886 -.0046 .032 Uiso calc R 1 . . H H110 1.2383 .1421 .0376 .031 Uiso calc R 1 . . H H11A 1.2751 .2425 .1825 .029 Uiso calc R 1 . . H H11B 1.3953 .1545 .1641 .029 Uiso calc R 1 . . H H11C 1.3133 .0563 .3224 .026 Uiso calc R 1 . . H H11D 1.3662 .1626 .3247 .026 Uiso calc R 1 . . H H11E 1.1415 .0767 .5017 .024 Uiso calc R 1 . . H H11F 1.1419 .1945 .4576 .024 Uiso calc R 1 . . H H21 -.1622 .3328 -.1266 .031 Uiso calc R 1 . . H H22 -.0350 .3312 -.2810 .033 Uiso calc R 1 . . H H24 .4915 .3841 -.2490 .031 Uiso calc R 1 . . H H27 .2650 .4233 .2515 .026 Uiso calc R 1 . . H H28 .2510 .4284 .4051 .031 Uiso calc R 1 . . H H29 -.0378 .3998 .5143 .031 Uiso calc R 1 . . H H210 -.3103 .3676 .4679 .029 Uiso calc R 1 . . H H21A -.4255 .4305 .2808 .027 Uiso calc R 1 . . H H21B -.4576 .3201 .3545 .027 Uiso calc R 1 . . H H21C -.3527 .2546 .2413 .026 Uiso calc R 1 . . H H21D -.4483 .3493 .1816 .026 Uiso calc R 1 . . H H21E -.1967 .2823 .0588 .024 Uiso calc R 1 . . H H21F -.2404 .3961 .0152 .024 Uiso calc R 1 . . H 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 C11 .0210(11) .0209(10) .0218(10) .0010(8) -.0068(8) -.0069(8) C12 .0275(12) .0232(11) .0211(10) -.0005(9) -.0088(8) -.0068(8) C13 .0300(12) .0251(11) .0166(10) .0022(9) -.0049(8) -.0064(8) Cl13 .0376(3) .0555(4) .0200(3) .0023(3) -.0037(2) -.0159(2) C14 .0198(11) .0237(11) .0218(10) .0021(8) -.0016(8) -.0067(8) C14A .0188(11) .0203(10) .0199(10) .0016(8) -.0060(8) -.0054(8) C41A .0205(11) .0156(10) .0191(10) -.0003(8) -.0031(8) -.0053(7) S15 .0153(3) .0354(3) .0206(3) .0030(2) -.00396(19) -.0118(2) C15A .0151(10) .0192(10) .0203(10) .0006(8) -.0044(7) -.0054(7) N16 .0153(9) .0237(9) .0161(8) .0023(7) -.0022(6) -.0076(6) C16A .0171(10) .0156(10) .0202(10) .0008(7) -.0011(8) -.0043(7) C16B .0192(10) .0166(10) .0199(10) .0048(8) -.0047(8) -.0058(7) C17 .0219(11) .0234(11) .0220(10) .0019(8) -.0047(8) -.0085(8) C18 .0301(12) .0250(11) .0267(11) .0023(9) -.0105(9) -.0119(8) C19 .0360(13) .0259(11) .0202(10) .0060(9) -.0054(9) -.0108(8) C110 .0259(12) .0264(11) .0239(11) .0043(9) .0000(8) -.0095(8) C10A .0209(11) .0164(10) .0220(10) .0048(8) -.0028(8) -.0049(7) C111 .0186(11) .0245(11) .0246(11) .0004(8) .0011(8) -.0053(8) C112 .0166(10) .0213(10) .0265(10) .0004(8) -.0027(8) -.0069(8) C113 .0149(10) .0215(10) .0239(10) -.0009(8) -.0039(8) -.0075(8) C12A .0156(10) .0171(10) .0196(10) -.0004(8) -.0025(8) -.0052(7) N114 .0133(8) .0221(9) .0176(8) .0022(6) -.0047(6) -.0075(6) C21 .0315(12) .0238(11) .0223(11) -.0005(9) -.0069(9) -.0080(8) C22 .0389(14) .0232(11) .0243(11) .0031(9) -.0118(9) -.0095(8) C23 .0428(14) .0241(11) .0176(10) .0100(9) -.0077(9) -.0080(8) Cl23 .0512(4) .0497(4) .0218(3) .0189(3) -.0085(2) -.0179(2) C24 .0264(12) .0297(12) .0202(11) .0083(9) -.0014(8) -.0077(8) C24A .0236(11) .0234(11) .0214(10) .0056(8) -.0068(8) -.0073(8) C42A .0260(12) .0169(10) .0173(10) .0022(8) -.0036(8) -.0053(7) S25 .0174(3) .0404(3) .0201(3) .0031(2) -.0030(2) -.0114(2) C25A .0168(10) .0189(10) .0197(10) .0014(8) -.0042(8) -.0053(7) N26 .0172(9) .0238(9) .0157(8) .0001(7) -.0016(6) -.0063(6) C26A .0162(10) .0148(9) .0192(10) .0023(7) -.0037(8) -.0040(7) C26B .0192(11) .0168(10) .0171(9) .0024(8) -.0043(7) -.0050(7) C27 .0180(11) .0260(11) .0223(10) .0020(8) -.0049(8) -.0086(8) C28 .0247(11) .0316(12) .0262(11) .0043(9) -.0111(9) -.0138(9) C29 .0320(13) .0297(11) .0187(10) .0039(9) -.0047(9) -.0115(8) C210 .0231(11) .0267(11) .0208(10) .0004(9) -.0001(8) -.0085(8) C21A .0197(11) .0157(10) .0208(10) -.0001(8) -.0017(8) -.0056(7) C211 .0157(10) .0250(11) .0233(10) -.0019(8) .0001(8) -.0067(8) C212 .0162(10) .0243(11) .0218(10) -.0017(8) -.0036(8) -.0050(8) C213 .0154(10) .0226(10) .0227(10) -.0017(8) -.0034(8) -.0084(8) C22A .0179(10) .0167(10) .0173(9) .0019(8) -.0040(7) -.0046(7) N214 .0161(9) .0237(9) .0170(8) -.0004(7) -.0023(6) -.0082(6) 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 C11 C12 . 1.385(3) no C11 C41A . 1.389(2) no C11 H11 . .9500 no C12 C13 . 1.386(3) no C12 H12 . .9500 no C13 C14 . 1.397(3) no C13 Cl13 . 1.7345(18) no C14 C14A . 1.382(2) no C14 H14 . .9500 no C14A C41A . 1.405(3) no C14A S15 . 1.7515(18) no C41A N114 . 1.381(2) no S15 C15A . 1.7667(18) no C15A N16 . 1.279(2) no C15A N114 . 1.379(2) no N16 C16A . 1.426(2) no C16A C12A . 1.343(2) no C16A C16B . 1.471(2) no C16B C17 . 1.397(3) no C16B C10A . 1.414(2) no C17 C18 . 1.387(2) no C17 H17 . .9500 no C18 C19 . 1.389(3) no C18 H18 . .9500 no C19 C110 . 1.390(3) no C19 H19 . .9500 no C110 C10A . 1.383(2) no C110 H110 . .9500 no C10A C111 . 1.514(3) no C111 C112 . 1.523(2) no C111 H11A . .9900 no C111 H11B . .9900 no C112 C12A . 1.502(2) no C112 H11C . .9900 no C112 H11D . .9900 no C113 N114 . 1.467(2) no C113 C12A . 1.498(2) no C113 H11E . .9900 no C113 H11F . .9900 no C21 C22 . 1.383(3) no C21 C42A . 1.389(3) no C21 H21 . .9500 no C22 C23 . 1.386(3) no C22 H22 . .9500 no C23 C24 . 1.391(3) no C23 Cl23 . 1.7391(18) no C24 C24A . 1.382(2) no C24 H24 . .9500 no C24A C42A . 1.397(3) no C24A S25 . 1.7519(18) no C42A N214 . 1.385(2) no S25 C25A . 1.7667(18) no C25A N26 . 1.280(2) no C25A N214 . 1.377(2) no N26 C26A . 1.426(2) no C26A C22A . 1.346(2) no C26A C26B . 1.475(2) no C26B C27 . 1.394(2) no C26B C21A . 1.407(2) no C27 C28 . 1.385(2) no C27 H27 . .9500 no C28 C29 . 1.388(3) no C28 H28 . .9500 no C29 C210 . 1.386(3) no C29 H29 . .9500 no C210 C21A . 1.387(2) no C210 H210 . .9500 no C21A C211 . 1.512(3) no C211 C212 . 1.520(2) no C211 H21A . .9900 no C211 H21B . .9900 no C212 C22A . 1.501(2) no C212 H21C . .9900 no C212 H21D . .9900 no C213 N214 . 1.462(2) no C213 C22A . 1.501(2) no C213 H21E . .9900 no C213 H21F . .9900 no