data_2011711 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 58 _journal_page_last 61 _publ_section_title ; Structural characterisation of 1-methylindole-3-carboxyaldehyde oxime derivatives ; loop_ _publ_author_name 'Janes, Robert W.' 'Potter, Brian S.' 'Naylor, Matthew A.' 'Ferguson, Amanda C.' 'Patel, Kantilal B.' 'Stratford, Michael R. L.' 'Wardman, Peter' 'Everett, Steven A.' _chemical_formula_moiety 'C11 H12 N2 O2' _chemical_formula_sum 'C11 H12 N2 O2' _chemical_formula_weight 204.23 _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 8.2351(2) _cell_length_b 15.8892(7) _cell_length_c 17.8070(11) _cell_angle_alpha 71.148(4) _cell_angle_beta 81.245(4) _cell_angle_gamma 75.124(3) _cell_volume 2125.02(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.277 _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 C1A .2798(6) .1015(3) .4897(3) .162(2) Uani d . 1 . . C H1A1 .3836 .0563 .4934 .194 Uiso calc R 1 . . H H1A2 .2109 .0870 .5386 .194 Uiso calc R 1 . . H H1A3 .3034 .1603 .4800 .194 Uiso calc R 1 . . H O2A .1958(4) .1026(2) .4281(2) .1520(13) Uani d D 1 . . O C3A .0366(4) .1559(2) .4164(2) .1007(11) Uani d D 1 . . C C4A -.0627(5) .1364(3) .3692(2) .1222(15) Uani d D 1 . . C H4A -.0195 .0874 .3488 .147 Uiso calc R 1 . . H C5A -.2192(4) .1869(2) .3529(2) .1072(13) Uani d D 1 . . C H5A -.2832 .1741 .3209 .129 Uiso calc R 1 . . H C6A -.2818(3) .25848(19) .38517(16) .0795(9) Uani d D 1 . . C C7A -.1856(3) .27979(16) .43241(14) .0659(7) Uani d D 1 . . C C8A -.0234(3) .22759(18) .44775(16) .0748(8) Uani d D 1 . . C H8A .0426 .2409 .4785 .090 Uiso calc R 1 . . H N9A -.4375(3) .31834(18) .37950(15) .0884(8) Uani d D 1 . . N C10A -.5717(4) .3209(3) .3337(2) .1269(16) Uani d D 1 . . C H10A -.5970 .2616 .3491 .152 Uiso calc R 1 . . H H10B -.5362 .3382 .2780 .152 Uiso calc R 1 . . H H10C -.6706 .3644 .3439 .152 Uiso calc R 1 . . H C11A -.4403(3) .37657(19) .42097(17) .0811(9) Uani d D 1 . . C H11A -.5314 .4237 .4259 .097 Uiso calc R 1 . . H C12A -.2913(3) .35703(16) .45472(14) .0656(7) Uani d D 1 . . C C13A -.2581(3) .40740(18) .50208(15) .0692(7) Uani d D 1 . . C H13A -.3447 .4537 .5128 .083 Uiso calc R 1 . . H N14A -.1175(3) .39278(15) .53043(13) .0673(6) Uani d D 1 . . N O15A -.1247(3) .45155(15) .57653(14) .0897(7) Uani d D 1 . . O H15A -.0318 .4426 .5927 .108 Uiso calc R 1 . . H C1B -.1246(4) .6800(2) .7871(2) .0933(10) Uani d . 1 . . C H1B1 -.2365 .7119 .7725 .112 Uiso calc R 1 . . H H1B2 -.0485 .7200 .7645 .112 Uiso calc R 1 . . H H1B3 -.1232 .6600 .8440 .112 Uiso calc R 1 . . H O2B -.0736(2) .60327(14) .75792(13) .0870(7) Uani d D 1 . . O C3B .0913(3) .55582(18) .76276(16) .0682(7) Uani d D 1 . . C C4B .1995(3) .5649(2) .81181(16) .0779(8) Uani d D 1 . . C H4B .1602 .6051 .8420 .093 Uiso calc R 1 . . H C5B .3620(3) .5155(2) .81580(16) .0776(8) Uani d D 1 . . C H5B .4335 .5213 .8487 .093 Uiso calc R 1 . . H C6B .4180(3) .45656(17) .76965(15) .0654(7) Uani d D 1 . . C C7B .3107(3) .44605(16) .72031(13) .0580(6) Uani d D 1 . . C C8B .1459(3) .49641(16) .71765(14) .0626(7) Uani d D 1 . . C H8B .0728 .4902 .6858 .075 Uiso calc R 1 . . H N9B .5759(2) .40192(16) .76053(13) .0745(7) Uani d D 1 . . N C10B .7229(4) .3936(3) .8009(2) .1017(11) Uani d D 1 . . C H10D .7068 .3611 .8562 .122 Uiso calc R 1 . . H H10E .7378 .4532 .7957 .122 Uiso calc R 1 . . H H10F .8211 .3608 .7774 .122 Uiso calc R 1 . . H C11B .5697(3) .35883(18) .70716(15) .0693(7) Uani d D 1 . . C H11B .6607 .3184 .6908 .083 Uiso calc R 1 . . H C12B .4124(3) .38231(17) .68027(14) .0611(7) Uani d D 1 . . C C13B .3709(3) .34638(18) .62310(14) .0634(7) Uani d D 1 . . C H13B .4559 .3058 .6036 .076 Uiso calc R 1 . . H N14B .2261(3) .36631(15) .59734(12) .0648(6) Uani d D 1 . . N O15B .2258(3) .31724(14) .54326(12) .0797(6) Uani d D 1 . . O H15B .1324 .3315 .5263 .096 Uiso calc R 1 . . H C1C .6215(5) .1051(3) .60024(19) .1031(12) Uani d . 1 . . C H1C1 .5313 .0837 .5894 .124 Uiso calc R 1 . . H H1C2 .7275 .0679 .5878 .124 Uiso calc R 1 . . H H1C3 .6155 .1673 .5682 .124 Uiso calc R 1 . . H O2C .6066(3) .10007(16) .68205(11) .0933(7) Uani d D 1 . . O C3C .7317(3) .11950(18) .71208(14) .0665(7) Uani d D 1 . . C C4C .8627(3) .1562(2) .66456(14) .0758(8) Uani d D 1 . . C H4C .8696 .1666 .6098 .091 Uiso calc R 1 . . H C5C .9813(3) .1772(2) .69749(13) .0749(8) Uani d D 1 . . C H5C 1.0683 .2020 .6657 .090 Uiso calc R 1 . . H C6C .9686(3) .16068(17) .77920(12) .0612(7) Uani d D 1 . . C C7C .8380(3) .12268(16) .82832(11) .0540(6) Uani d D 1 . . C C8C .7185(3) .10269(16) .79368(12) .0589(7) Uani d D 1 . . C H8C .6306 .0783 .8249 .071 Uiso calc R 1 . . H N9C 1.0707(3) .17415(16) .82718(12) .0705(6) Uani d D 1 . . N C10C 1.2178(4) .2135(2) .80034(19) .0967(11) Uani d D 1 . . C H10G 1.1838 .2762 .7695 .116 Uiso calc R 1 . . H H10H 1.2948 .1804 .7681 .116 Uiso calc R 1 . . H H10I 1.2722 .2100 .8456 .116 Uiso calc R 1 . . H C11C 1.0085(3) .14496(18) .90371(13) .0686(7) Uani d D 1 . . C H11C 1.0556 .1470 .9472 .082 Uiso calc R 1 . . H C12C .8684(3) .11230(17) .90879(12) .0571(6) Uani d D 1 . . C C13C .7832(3) .07139(18) .98329(13) .0615(7) Uani d D 1 . . C H13C .8211 .0708 1.0301 .074 Uiso calc R 1 . . H N14C .6586(3) .03604(14) .98809(11) .0616(6) Uani d D 1 . . N O15C .6038(3) -.00210(16) 1.06859(10) .0845(6) Uani d D 1 . . O H15C .5182 -.0203 1.0704 .101 Uiso calc R 1 . . H C1D .6362(7) .0596(3) 1.2327(2) .148(2) Uani d . 1 . . C H1D1 .5233 .0562 1.2545 .177 Uiso calc R 1 . . H H1D2 .7096 .0395 1.2751 .177 Uiso calc R 1 . . H H1D3 .6731 .0212 1.1986 .177 Uiso calc R 1 . . H O2D .6403(3) .15132(15) 1.18796(14) .1108(8) Uani d D 1 . . O C3D .7878(4) .17145(18) 1.14763(17) .0846(10) Uani d D 1 . . C C4D .9437(4) .11039(19) 1.15949(19) .0998(12) Uani d D 1 . . C H4D .9498 .0525 1.1956 .120 Uiso calc R 1 . . H C5D 1.0876(4) .13441(18) 1.11874(19) .1014(12) Uani d D 1 . . C H5D 1.1914 .0935 1.1267 .122 Uiso calc R 1 . . H C6D 1.0755(3) .22120(16) 1.06515(16) .0803(9) Uani d D 1 . . C C7D .9186(3) .28396(15) 1.05226(14) .0663(7) Uani d D 1 . . C C8D .7749(3) .25784(16) 1.09412(15) .0738(8) Uani d D 1 . . C H8D .6704 .2980 1.0864 .089 Uiso calc R 1 . . H N9D 1.1984(3) .26227(17) 1.01692(16) .0907(8) Uani d D 1 . . N C10D 1.3792(3) .2233(3) 1.0141(3) .1327(16) Uani d D 1 . . C H10J 1.4002 .1652 1.0046 .159 Uiso calc R 1 . . H H10K 1.4211 .2155 1.0639 .159 Uiso calc R 1 . . H H10L 1.4353 .2635 .9720 .159 Uiso calc R 1 . . H C11D 1.1243(3) .34815(18) .97538(18) .0848(9) Uani d D 1 . . C H11D 1.1815 .3895 .9390 .102 Uiso calc R 1 . . H C12D .9544(3) .36572(15) .99418(15) .0663(7) Uani d D 1 . . C C13D .8455(3) .45320(15) .96149(16) .0677(7) Uani d D 1 . . C H13D .8922 .4983 .9238 .081 Uiso calc R 1 . . H N14D .6890(3) .47187(13) .98148(13) .0652(6) Uani d D 1 . . N O15D .6150(2) .56374(12) .94160(14) .0876(7) Uani d D 1 . . O H15D .5135 .5740 .9541 .105 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 C1A .153(4) .163(4) .176(5) .061(3) -.089(4) -.100(4) O2A .146(3) .156(3) .175(3) .051(2) -.068(2) -.116(2) C3A .115(3) .103(3) .095(2) .003(2) -.030(2) -.056(2) C4A .160(4) .124(3) .112(3) -.015(3) -.038(3) -.075(3) C5A .136(4) .122(3) .086(2) -.034(3) -.035(2) -.044(2) C6A .101(3) .090(2) .0569(17) -.034(2) -.0160(16) -.0205(16) C7A .0773(19) .0741(18) .0490(14) -.0248(16) -.0089(13) -.0138(13) C8A .085(2) .084(2) .0616(17) -.0123(17) -.0172(15) -.0306(15) N9A .0838(19) .112(2) .0733(17) -.0350(17) -.0227(14) -.0151(16) C10A .122(3) .164(4) .111(3) -.061(3) -.051(3) -.020(3) C11A .075(2) .089(2) .078(2) -.0230(17) -.0117(17) -.0153(17) C12A .0664(18) .0728(18) .0581(16) -.0252(15) -.0060(13) -.0117(14) C13A .0619(18) .0686(18) .0768(19) -.0174(14) -.0005(15) -.0213(15) N14A .0714(16) .0714(15) .0676(14) -.0210(12) .0004(12) -.0305(12) O15A .0870(15) .0991(16) .1066(17) -.0250(13) .0000(13) -.0621(14) C1B .102(3) .089(2) .099(2) -.0067(19) -.022(2) -.047(2) O2B .0775(15) .1044(16) .1004(16) -.0109(12) -.0099(12) -.0652(14) C3B .0664(18) .0823(19) .0648(17) -.0218(16) -.0039(14) -.0301(15) C4B .087(2) .091(2) .0729(19) -.0235(18) -.0081(16) -.0437(17) C5B .084(2) .095(2) .0716(19) -.0255(18) -.0151(16) -.0392(17) C6B .0690(18) .0751(18) .0610(16) -.0266(15) -.0073(14) -.0228(14) C7B .0617(16) .0684(17) .0497(14) -.0272(14) -.0004(12) -.0174(12) C8B .0703(18) .0763(18) .0534(15) -.0293(15) -.0026(13) -.0264(14) N9B .0674(16) .0885(17) .0774(16) -.0206(13) -.0155(13) -.0309(14) C10B .082(2) .120(3) .119(3) -.016(2) -.034(2) -.050(2) C11B .0678(18) .0724(18) .0747(18) -.0206(15) -.0045(15) -.0277(15) C12B .0643(17) .0675(17) .0584(15) -.0245(14) .0007(13) -.0224(13) C13B .0635(17) .0691(17) .0636(16) -.0215(14) .0027(14) -.0258(14) N14B .0742(16) .0705(14) .0610(13) -.0228(12) -.0010(11) -.0312(11) O15B .0816(14) .0936(15) .0828(14) -.0185(12) -.0094(11) -.0511(12) C1C .143(3) .107(3) .078(2) -.031(2) -.032(2) -.040(2) O2C .1182(18) .1147(17) .0627(13) -.0555(15) -.0198(12) -.0188(12) C3C .0797(19) .0667(17) .0574(16) -.0239(15) -.0094(14) -.0164(13) C4C .092(2) .083(2) .0522(16) -.0271(18) -.0015(16) -.0159(15) C5C .078(2) .080(2) .0586(17) -.0279(16) .0055(15) -.0070(15) C6C .0622(16) .0615(16) .0590(16) -.0195(13) -.0041(13) -.0125(13) C7C .0565(15) .0515(14) .0519(14) -.0134(12) -.0042(12) -.0113(11) C8C .0652(17) .0588(15) .0511(14) -.0179(13) -.0046(12) -.0108(12) N9C .0642(15) .0771(15) .0696(15) -.0301(12) -.0058(12) -.0093(12) C10C .084(2) .112(3) .097(2) -.056(2) -.0069(19) -.008(2) C11C .0711(18) .0730(18) .0633(17) -.0202(15) -.0119(14) -.0161(14) C12C .0544(15) .0619(16) .0558(15) -.0161(13) -.0060(12) -.0155(12) C13C .0619(17) .0726(18) .0507(14) -.0168(14) -.0046(12) -.0176(13) N14C .0629(14) .0699(14) .0455(12) -.0160(11) .0031(10) -.0106(10) O15C .0875(16) .1137(17) .0486(11) -.0409(13) .0063(10) -.0102(10) C1D .279(6) .099(3) .088(3) -.099(4) -.034(3) -.007(2) O2D .161(3) .0855(16) .0940(17) -.0560(17) -.0207(17) -.0101(13) C3D .123(3) .067(2) .073(2) -.021(2) -.029(2) -.0221(17) C4D .153(4) .062(2) .089(3) -.012(2) -.043(3) -.0226(18) C5D .129(3) .066(2) .109(3) .024(2) -.058(3) -.039(2) C6D .085(2) .076(2) .090(2) .0018(18) -.0270(19) -.0450(18) C7D .0713(19) .0637(17) .0727(18) -.0025(15) -.0246(15) -.0334(15) C8D .094(2) .0617(18) .0725(18) -.0109(16) -.0268(17) -.0247(15) N9D .0693(18) .091(2) .117(2) .0140(16) -.0275(17) -.0541(18) C10D .072(2) .130(3) .199(5) .027(2) -.037(3) -.078(3) C11D .071(2) .088(2) .102(2) -.0055(18) -.0142(18) -.044(2) C12D .0589(17) .0685(18) .0768(18) -.0046(14) -.0140(14) -.0322(15) C13D .0606(18) .0678(18) .0750(18) -.0130(14) -.0086(14) -.0211(15) N14D .0601(14) .0574(13) .0749(15) -.0033(11) -.0153(12) -.0184(11) O15D .0690(13) .0657(13) .1087(17) -.0018(10) -.0151(13) -.0063(12) 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 O2A . 1.375(4) yes O2A C3A . 1.371(3) yes C3A C8A . 1.375(3) yes C3A C4A . 1.407(3) yes C4A C5A . 1.350(3) yes C5A C6A . 1.386(3) yes C6A N9A . 1.382(3) yes C6A C7A . 1.405(3) yes C7A C8A . 1.394(3) yes C7A C12A . 1.443(3) yes N9A C11A . 1.352(3) yes N9A C10A . 1.455(3) yes C11A C12A . 1.368(3) yes C12A C13A . 1.430(3) yes C13A N14A . 1.270(3) yes N14A O15A . 1.415(2) yes C1B O2B . 1.418(3) yes O2B C3B . 1.373(3) no C3B C8B . 1.379(3) no C3B C4B . 1.401(3) no C4B C5B . 1.366(3) no C5B C6B . 1.388(3) no C6B N9B . 1.385(3) no C6B C7B . 1.409(3) no C7B C8B . 1.387(3) no C7B C12B . 1.444(3) no N9B C11B . 1.352(3) no N9B C10B . 1.456(3) no C11B C12B . 1.368(3) no C12B C13B . 1.436(2) no C13B N14B . 1.270(3) yes N14B O15B . 1.422(2) yes C1C O2C . 1.421(3) yes O2C C3C . 1.371(2) no C3C C8C . 1.382(3) no C3C C4C . 1.395(3) no C4C C5C . 1.371(3) no C5C C6C . 1.385(3) no C6C N9C . 1.383(2) no C6C C7C . 1.411(3) no C7C C8C . 1.386(2) no C7C C12C . 1.442(2) no N9C C11C . 1.355(3) no N9C C10C . 1.452(3) no C11C C12C . 1.362(3) no C12C C13C . 1.438(2) no C13C N14C . 1.271(2) yes N14C O15C . 1.417(2) yes C1D O2D . 1.423(4) yes O2D C3D . 1.371(3) no C3D C8D . 1.384(3) no C3D C4D . 1.394(3) no C4D C5D . 1.367(3) no C5D C6D . 1.389(3) no C6D N9D . 1.379(3) no C6D C7D . 1.414(3) no C7D C8D . 1.383(3) no C7D C12D . 1.442(3) no N9D C11D . 1.356(3) no N9D C10D . 1.458(3) no C11D C12D . 1.366(3) no C12D C13D . 1.439(3) no C13D N14D . 1.268(3) yes N14D O15D . 1.418(2) yes