#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2200149.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2200149 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o287 _journal_page_last o288 _publ_section_title ; 2-Chloro-3-(4-methylpiperazino)-1,4-naphthoquinone ; loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _chemical_formula_moiety 'C15 H15 Cl N2 O2' _chemical_formula_sum 'C15 H15 Cl N2 O2' _chemical_formula_iupac 'C15 H15 Cl N2 O2' _chemical_formula_weight 290.74 _chemical_melting_point '387-400 K' _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 12.379(3) _cell_length_b 9.389(2) _cell_length_c 12.995(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.60(3) _cell_angle_gamma 90.00 _cell_volume 1350.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.430 _diffrn_ambient_temperature 150(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 C1 .89909(14) -.03254(17) .23676(13) .0240(4) Uani d . 1 . . C O1 .79363(10) -.01992(14) .16625(10) .0383(3) Uani d . 1 . . O C2 .99739(14) .03580(16) .22078(12) .0211(3) Uani d . 1 . . C Cl2 .94716(4) .15460(5) .10630(3) .03148(16) Uani d . 1 . . Cl C3 1.11721(13) .01831(16) .29166(12) .0185(3) Uani d . 1 . . C N31 1.21129(12) .06901(14) .27450(10) .0220(3) Uani d . 1 . . N C32 1.20713(15) .08709(19) .16036(12) .0248(4) Uani d . 1 . . C H321 1.1918 .1882 .1367 .031 Uiso calc R 1 . . H H322 1.1406 .0293 .1029 .031 Uiso calc R 1 . . H C33 1.32618(15) .04042(18) .16517(13) .0245(4) Uani d . 1 . . C H331 1.3374 -.0628 .1823 .031 Uiso calc R 1 . . H H332 1.3242 .0560 .0890 .031 Uiso calc R 1 . . H N34 1.42799(12) .11799(14) .25238(10) .0209(3) Uani d . 1 . . N C35 1.43165(14) .09283(17) .36551(12) .0220(4) Uani d . 1 . . C H351 1.5003 .1456 .4253 .027 Uiso calc R 1 . . H H352 1.4439 -.0099 .3843 .027 Uiso calc R 1 . . H C36 1.31504(14) .14127(17) .36517(12) .0213(4) Uani d . 1 . . C H361 1.3175 .1204 .4409 .027 Uiso calc R 1 . . H H362 1.3062 .2455 .3527 .027 Uiso calc R 1 . . H C37 1.54101(15) .06948(18) .25506(14) .0262(4) Uani d . 1 . . C H371 1.6082 .1248 .3121 .033 Uiso calc R 1 . . H H372 1.5379 .0826 .1790 .033 Uiso calc R 1 . . H H373 1.5529 -.0316 .2759 .033 Uiso calc R 1 . . H C4 1.15166(14) -.07536(16) .39713(12) .0190(3) Uani d . 1 . . C O4 1.25679(9) -.10712(12) .45637(8) .0258(3) Uani d . 1 . . O C5 1.08581(15) -.20685(17) .52433(12) .0248(4) Uani d . 1 . . C H5 1.1684 -.2193 .5774 .031 Uiso calc R 1 . . H C6 .99591(17) -.26450(19) .54739(14) .0306(4) Uani d . 1 . . C H6 1.0171 -.3161 .6167 .038 Uiso calc R 1 . . H C7 .87551(15) -.24747(18) .47035(14) .0286(4) Uani d . 1 . . C H7 .8145 -.2880 .4866 .036 Uiso calc R 1 . . H C8 .84372(15) -.17140(18) .36950(14) .0260(4) Uani d . 1 . . C H8 .7610 -.1596 .3167 .032 Uiso calc R 1 . . H C9 .93340(14) -.11219(16) .34565(13) .0209(3) Uani d . 1 . . C C10 1.05473(14) -.13066(16) .42324(12) .0190(3) Uani d . 1 . . C 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 C1 .0193(8) .0227(9) .0287(8) .0012(6) .0097(7) -.0001(6) O1 .0167(6) .0484(8) .0409(7) .0000(6) .0048(5) .0138(6) C2 .0222(8) .0209(8) .0193(7) .0015(6) .0085(6) .0021(6) Cl2 .0256(3) .0350(3) .0296(2) .00451(18) .00853(18) .01337(17) C3 .0195(8) .0190(8) .0190(7) -.0010(6) .0105(6) -.0028(6) N31 .0186(7) .0308(8) .0177(6) -.0061(6) .0090(5) -.0026(5) C32 .0239(9) .0338(10) .0173(7) -.0052(7) .0097(7) .0013(6) C33 .0280(9) .0296(9) .0192(7) -.0063(7) .0135(7) -.0024(6) N34 .0200(7) .0248(7) .0207(6) -.0027(5) .0116(6) -.0004(5) C35 .0205(8) .0262(9) .0195(7) -.0016(7) .0093(7) -.0002(6) C36 .0208(8) .0242(9) .0195(7) -.0053(6) .0097(6) -.0037(6) C37 .0247(9) .0294(9) .0295(8) -.0001(7) .0165(7) .0010(7) C4 .0188(8) .0208(8) .0182(7) .0003(6) .0089(6) -.0031(6) O4 .0170(6) .0353(7) .0244(6) .0015(5) .0087(5) .0042(5) C5 .0246(9) .0274(9) .0229(8) -.0007(7) .0111(7) -.0005(6) C6 .0364(10) .0336(10) .0290(8) -.0029(8) .0211(8) .0024(7) C7 .0287(10) .0292(10) .0378(9) -.0057(7) .0237(8) -.0036(7) C8 .0192(8) .0262(9) .0358(9) -.0018(7) .0153(7) -.0064(7) C9 .0199(8) .0191(8) .0261(8) -.0007(6) .0123(7) -.0029(6) C10 .0199(8) .0196(8) .0212(7) -.0007(6) .0124(6) -.0026(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 C1 O1 . 1.2193(19) ? C1 C2 . 1.470(2) ? C1 C9 . 1.484(2) ? C2 C3 . 1.361(2) ? C2 Cl2 . 1.7365(15) ? C3 N31 . 1.3657(19) ? C3 C4 . 1.520(2) ? N31 C36 . 1.464(2) ? N31 C32 . 1.4708(18) ? C32 C33 . 1.512(2) ? C32 H321 . .99 ? C32 H322 . .99 ? C33 N34 . 1.457(2) ? C33 H331 . .99 ? C33 H332 . .99 ? N34 C37 . 1.457(2) ? N34 C35 . 1.4695(19) ? C35 C36 . 1.512(2) ? C35 H351 . .99 ? C35 H352 . .99 ? C36 H361 . .99 ? C36 H362 . .99 ? C37 H371 . .98 ? C37 H372 . .98 ? C37 H373 . .98 ? C4 O4 . 1.2157(19) ? C4 C10 . 1.480(2) ? C5 C6 . 1.386(2) ? C5 C10 . 1.390(2) ? C5 H5 . .95 ? C6 C7 . 1.383(2) ? C6 H6 . .95 ? C7 C8 . 1.386(2) ? C7 H7 . .95 ? C8 C9 . 1.395(2) ? C8 H8 . .95 ? C9 C10 . 1.395(2) ?