#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012228.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_2012228 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1116 _journal_page_last 1117 _publ_section_title ; Methyl (SR)-10-chloro-1,2,3,4,5,6-hexahydro-6-hydroxy-8-methoxy-1-methyl- 1,9-phenanthroline-6-carboxylate ; loop_ _publ_author_name 'Usman, Anwar' 'Razak, Ibrahim Abdul' 'Chantrapromma, Suchada' 'Fun, Hoong-Kun' 'Sarkar, Tarun K.' 'Basak, Sankar' 'Nigam, Gur Dayal' _chemical_formula_moiety 'C16 H19 Cl N2 O4' _chemical_formula_sum 'C16 H19 Cl N2 O4' _chemical_formula_weight 338.78 _chemical_melting_point 426K _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 9.2081(4) _cell_length_b 9.4835(4) _cell_length_c 11.1287(6) _cell_angle_alpha 100.5740(10) _cell_angle_beta 101.7510(10) _cell_angle_gamma 111.8820(10) _cell_volume 846.14(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.330 _diffrn_ambient_temperature 293(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 Cl1 .45819(11) .21311(9) .18714(8) .0550(3) Uani d . 1 . . Cl O1 .3028(2) .7970(3) .3657(2) .0503(6) Uani d . 1 . . O H1A .3411 .8839 .4188 .075 Uiso calc R 1 . . H O2 -.0171(3) .3112(3) .0170(2) .0575(6) Uani d . 1 . . O O3 .5669(3) .8382(2) .2006(2) .0521(6) Uani d . 1 . . O O4 .6409(3) 1.0135(3) .3897(2) .0564(7) Uani d . 1 . . O N1 .2167(3) .2805(3) .0998(2) .0391(6) Uani d . 1 . . N N2 .7440(3) .5413(3) .3051(3) .0481(7) Uani d . 1 . . N C1 .3702(4) .3479(3) .1796(3) .0362(6) Uani d . 1 . . C C2 .4532(3) .5035(3) .2557(3) .0323(6) Uani d . 1 . . C C3 .6239(3) .5831(3) .3428(3) .0361(6) Uani d . 1 . . C C4 .9080(5) .6318(8) .3933(5) .108(2) Uani d D 1 . . C H4A .9669 .5658 .3879 .130 Uiso calc R 1 . . H H4B .9632 .7219 .3640 .130 Uiso calc R 1 . . H C5 .9225(6) .6899(9) .5249(5) .149(3) Uani d D 1 . . C H5A 1.0357 .7648 .5682 .179 Uiso calc R 1 . . H H5B .9002 .6015 .5614 .179 Uiso calc R 1 . . H C6 .8205(4) .7653(5) .5543(4) .0600(10) Uani d D 1 . . C H6A .8735 .8766 .5587 .072 Uiso calc R 1 . . H H6B .8065 .7587 .6374 .072 Uiso calc R 1 . . H C7 .6541(3) .6888(3) .4544(3) .0372(7) Uani d . 1 . . C C8 .5202(4) .7338(4) .4785(3) .0398(7) Uani d . 1 . . C H8A .5668 .8331 .5459 .048 Uiso calc R 1 . . H H8B .4444 .6526 .5056 .048 Uiso calc R 1 . . H C9 .4305(3) .7510(3) .3549(3) .0362(7) Uani d . 1 . . C C10 .3563(3) .5894(3) .2559(3) .0315(6) Uani d . 1 . . C C11 .1993(4) .5246(4) .1770(3) .0401(7) Uani d . 1 . . C H11A .1362 .5816 .1761 .048 Uiso calc R 1 . . H C12 .1361(3) .3693(4) .0974(3) .0392(7) Uani d . 1 . . C C13 .7499(5) .5374(5) .1754(4) .0674(11) Uani d . 1 . . C H13A .8091 .4777 .1515 .101 Uiso calc R 1 . . H H13B .8043 .6437 .1708 .101 Uiso calc R 1 . . H H13C .6404 .4883 .1179 .101 Uiso calc R 1 . . H C14 .5584(4) .8815(3) .3185(3) .0375(7) Uani d . 1 . . C C15 .6896(6) .9556(5) .1650(4) .0739(12) Uani d . 1 . . C H15A .6901 .9110 .0805 .111 Uiso calc R 1 . . H H15B .7954 .9884 .2247 .111 Uiso calc R 1 . . H H15C .6650 1.0456 .1663 .111 Uiso calc R 1 . . H C16 -.0894(5) .1510(4) -.0618(4) .0714(12) Uani d . 1 . . C H16A -.1965 .1265 -.1155 .107 Uiso calc R 1 . . H H16B -.0984 .0810 -.0086 .107 Uiso calc R 1 . . H H16C -.0219 .1379 -.1142 .107 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 Cl1 .0605(6) .0455(5) .0550(5) .0324(4) .0027(4) .0000(4) O1 .0399(12) .0559(13) .0524(14) .0288(11) .0101(10) -.0046(11) O2 .0366(12) .0470(13) .0606(15) .0086(11) -.0128(11) .0016(12) O3 .0679(15) .0448(12) .0315(12) .0122(11) .0191(11) .0043(10) O4 .0703(16) .0379(12) .0477(14) .0123(12) .0257(13) -.0042(11) N1 .0363(14) .0359(13) .0331(13) .0101(11) .0022(11) .0029(11) N2 .0299(13) .0573(16) .0555(17) .0235(13) .0066(12) .0089(14) C1 .0380(16) .0395(16) .0313(15) .0188(14) .0098(13) .0060(13) C2 .0310(15) .0369(15) .0265(14) .0137(12) .0079(11) .0059(12) C3 .0298(15) .0398(16) .0372(16) .0155(13) .0062(12) .0109(13) C4 .044(2) .158(5) .109(4) .061(3) -.002(3) -.006(4) C5 .052(3) .231(8) .113(5) .076(4) -.029(3) -.041(5) C6 .0373(19) .068(2) .051(2) .0119(18) -.0048(16) .0042(18) C7 .0302(15) .0411(16) .0306(15) .0094(13) .0028(12) .0078(13) C8 .0418(17) .0426(17) .0276(15) .0138(14) .0092(13) .0037(13) C9 .0316(15) .0411(16) .0328(15) .0173(13) .0082(12) .0013(13) C10 .0270(14) .0334(14) .0286(14) .0108(12) .0065(11) .0029(11) C11 .0320(15) .0415(16) .0411(17) .0167(13) .0045(13) .0040(14) C12 .0260(15) .0419(17) .0378(16) .0066(13) .0030(12) .0086(14) C13 .060(2) .089(3) .072(3) .040(2) .040(2) .026(2) C14 .0399(16) .0383(16) .0356(16) .0211(14) .0090(13) .0066(14) C15 .098(3) .060(2) .059(2) .019(2) .047(2) .015(2) C16 .050(2) .045(2) .077(3) -.0012(18) -.016(2) .009(2) 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 Cl1 C1 . 1.755(3) ? O1 C9 . 1.417(3) ? O1 H1A . .8200 ? O2 C12 . 1.348(3) ? O2 C16 . 1.428(4) ? O3 C14 . 1.329(3) ? O3 C15 . 1.442(4) ? O4 C14 . 1.206(3) ? N1 C12 . 1.314(4) yes N1 C1 . 1.343(4) yes N2 C3 . 1.418(4) yes N2 C4 . 1.450(5) yes N2 C13 . 1.451(5) ? C1 C2 . 1.385(4) ? C2 C10 . 1.415(4) yes C2 C3 . 1.485(4) yes C3 C7 . 1.349(4) yes C4 C5 . 1.426(4) ? C4 H4A . .9700 ? C4 H4B . .9700 ? C5 C6 . 1.429(4) ? C5 H5A . .9700 ? C5 H5B . .9700 ? C6 C7 . 1.514(4) yes C6 H6A . .9700 ? C6 H6B . .9700 ? C7 C8 . 1.503(4) yes C8 C9 . 1.524(4) yes C8 H8A . .9700 ? C8 H8B . .9700 ? C9 C10 . 1.524(4) yes C9 C14 . 1.541(4) ? C10 C11 . 1.364(4) ? C11 C12 . 1.402(4) ? C11 H11A . .9300 ? C13 H13A . .9600 ? C13 H13B . .9600 ? C13 H13C . .9600 ? C15 H15A . .9600 ? C15 H15B . .9600 ? C15 H15C . .9600 ? C16 H16A . .9600 ? C16 H16B . .9600 ? C16 H16C . .9600 ? _cod_database_code 2012228