data_2012099 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 848 _journal_page_last 850 _publ_section_title ; 11-Chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-[1,3]oxazino [3,2-d][1,4]benzodiazepine-4,7(6H)-dione (Ketazolam) ; loop_ _publ_author_name 'Vega, Daniel' "Fern\'andez, Daniel" "Echeverr\'ia, Gustavo" _chemical_formula_moiety 'C20 H17 Cl N2 O3' _chemical_formula_sum 'C20 H17 Cl N2 O3' _chemical_formula_weight 368.81 _chemical_melting_point 455 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M ' P 21/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 8.6326(9) _cell_length_b 13.1190(10) _cell_length_c 15.505(4) _cell_angle_alpha 90 _cell_angle_beta 96.190(10) _cell_angle_gamma 90 _cell_volume 1745.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.403 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 O1 .0413(2) .31121(17) -.17074(14) .0406(6) Uani d . 1 . . O O4 -.0803(3) .0213(2) -.14088(19) .0619(8) Uani d . 1 . . O O7 .3936(3) -.0127(2) -.09127(18) .0631(8) Uani d . 1 . . O N5 .0977(3) .1480(2) -.11214(17) .0392(7) Uani d . 1 . . N N8 .4486(3) .1530(2) -.06120(18) .0443(7) Uani d . 1 . . N C2 -.0752(4) .2699(3) -.2273(2) .0430(9) Uani d . 1 . . C C3 -.1081(4) .1718(3) -.2243(2) .0461(9) Uani d . 1 . . C H3 -.1826 .1445 -.2657 .055 Uiso calc R 1 . . H C4 -.0314(4) .1053(3) -.1583(2) .0458(9) Uani d . 1 . . C C6 .1877(4) .0886(3) -.0445(2) .0457(9) Uani d . 1 . . C H6B .1368 .0236 -.0378 .055 Uiso calc R 1 . . H H6A .1917 .1248 .0103 .055 Uiso calc R 1 . . H C7 .3524(4) .0705(3) -.0671(2) .0467(9) Uani d . 1 . . C C8 .6064(4) .1430(4) -.0865(3) .0686(13) Uani d . 1 . . C H8C .6224 .0744 -.1051 .103 Uiso calc R 1 . . H H8B .6808 .1588 -.0378 .103 Uiso calc R 1 . . H H8A .6194 .1892 -.1332 .103 Uiso calc R 1 . . H C9 .4007(4) .2487(3) -.0313(2) .0403(8) Uani d . 1 . . C C10 .4911(4) .3002(3) .0345(2) .0514(10) Uani d . 1 . . C H10 .5854 .2722 .0578 .062 Uiso calc R 1 . . H C11 .4437(4) .3913(3) .0655(2) .0543(11) Uani d . 1 . . C H11 .5062 .4258 .1085 .065 Uiso calc R 1 . . H C12 .3031(4) .4311(3) .0324(2) .0473(9) Uani d . 1 . . C C13 .2120(4) .3836(3) -.0330(2) .0407(9) Uani d . 1 . . C H13 .1169 .4121 -.0544 .049 Uiso calc R 1 . . H C14 .2610(4) .2926(2) -.0677(2) .0349(8) Uani d . 1 . . C C15 .1648(3) .2412(3) -.1429(2) .0362(8) Uani d . 1 . . C C16 .2586(3) .2249(3) -.2203(2) .0347(8) Uani d . 1 . . C C17 .2796(4) .1313(3) -.2568(2) .0464(9) Uani d . 1 . . C H17 .2349 .0737 -.2346 .056 Uiso calc R 1 . . H C18 .3667(4) .1218(3) -.3261(3) .0620(12) Uani d . 1 . . C H18 .3821 .0579 -.3497 .074 Uiso calc R 1 . . H C19 .4300(5) .2061(4) -.3601(3) .0654(12) Uani d . 1 . . C H19 .488 .1996 -.407 .078 Uiso calc R 1 . . H C20 .4083(4) .2997(3) -.3255(3) .0617(12) Uani d . 1 . . C H20 .4509 .3571 -.349 .074 Uiso calc R 1 . . H C21 .3234(4) .3092(3) -.2558(2) .0507(10) Uani d . 1 . . C H21 .3093 .3734 -.2323 .061 Uiso calc R 1 . . H C22 -.1521(4) .3485(3) -.2865(2) .0597(11) Uani d . 1 . . C H22C -.2339 .3174 -.3244 .09 Uiso calc R 1 . . H H22B -.0767 .378 -.3203 .09 Uiso calc R 1 . . H H22A -.1951 .4008 -.2529 .09 Uiso calc R 1 . . H Cl1 .23773(14) .54380(9) .07470(7) .0750(4) 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 O1 .0346(12) .0436(14) .0422(13) .0111(11) -.0026(11) .0006(11) O4 .0481(16) .0479(17) .089(2) -.0120(14) .0039(14) .0032(15) O7 .0612(17) .0491(17) .077(2) .0150(14) .0010(14) .0026(15) N5 .0331(15) .0408(17) .0432(17) -.0019(14) .0020(13) .0064(14) N8 .0341(16) .0487(19) .0498(18) .0080(15) .0027(13) .0110(15) C2 .0284(18) .066(3) .0343(19) .0053(18) .0037(15) .0013(19) C3 .0331(19) .059(3) .046(2) -.0071(18) -.0007(16) -.003(2) C4 .035(2) .050(2) .053(2) .0003(19) .0092(18) -.006(2) C6 .045(2) .045(2) .047(2) -.0006(18) .0029(17) .0128(18) C7 .042(2) .049(2) .047(2) .008(2) -.0024(17) .0123(19) C8 .040(2) .080(3) .088(3) .015(2) .016(2) .009(3) C9 .0327(18) .047(2) .0420(19) -.0006(17) .0058(16) .0085(17) C10 .039(2) .071(3) .042(2) -.006(2) -.0032(17) .008(2) C11 .054(2) .068(3) .040(2) -.018(2) .0019(19) -.007(2) C12 .053(2) .053(2) .038(2) -.008(2) .0136(18) -.0070(18) C13 .0394(19) .046(2) .037(2) .0008(17) .0030(16) .0003(17) C14 .0340(17) .039(2) .0316(17) -.0023(16) .0036(14) .0045(16) C15 .0289(17) .040(2) .0397(18) .0038(16) .0015(15) .0024(17) C16 .0298(17) .0382(19) .0352(18) .0020(16) -.0003(15) .0019(16) C17 .046(2) .047(2) .047(2) -.0007(18) .0064(18) -.0071(18) C18 .059(3) .066(3) .062(3) .002(2) .011(2) -.024(2) C19 .054(3) .093(4) .052(3) -.003(3) .021(2) -.011(3) C20 .062(3) .065(3) .062(3) -.009(2) .024(2) .004(2) C21 .051(2) .049(2) .054(2) -.0009(19) .0115(19) -.002(2) C22 .052(2) .074(3) .051(2) .013(2) -.0054(19) .004(2) Cl1 .0880(8) .0695(7) .0698(7) -.0057(6) .0188(6) -.0287(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 O1 C2 . 1.372(4) ? O1 C15 . 1.438(4) Y O4 C4 . 1.221(4) Y O7 C7 . 1.219(4) Y N5 C4 . 1.377(4) Y N5 C15 . 1.455(4) Y N5 C6 . 1.462(4) Y N8 C7 . 1.361(4) Y N8 C9 . 1.416(4) Y N8 C8 . 1.463(4) ? C2 C3 . 1.320(5) ? C2 C22 . 1.488(5) ? C3 C4 . 1.449(5) ? C6 C7 . 1.519(5) Y C9 C10 . 1.390(5) ? C9 C14 . 1.399(4) ? C10 C11 . 1.367(5) ? C11 C12 . 1.369(5) ? C12 C13 . 1.364(5) ? C12 Cl1 . 1.736(4) Y C13 C14 . 1.395(4) ? C14 C15 . 1.515(4) Y C15 C16 . 1.534(4) Y C16 C17 . 1.372(5) ? C16 C21 . 1.381(5) ? C17 C18 . 1.382(5) ? C18 C19 . 1.365(6) ? C19 C20 . 1.360(5) ? C20 C21 . 1.375(5) ?