#------------------------------------------------------------------------------ #$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $ #$Revision: 481 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006621.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_2006621 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1997 _journal_volume 53 _journal_page_first 1447 _journal_page_last 1449 _publ_section_title ; Tubingensin B, a Cytotoxic Carbazole Alkaloid from the Sclerotia of Aspergillus tubingensis ; loop_ _publ_author_name 'Swenson, Dale C.' 'TePaske, Mark R.' 'Baenziger, Norman C.' 'Gloer, James B.' _chemical_formula_moiety 'C28 H35 N1 O1,0.5C1 H1 Cl3' _chemical_formula_sum 'C28.5 H35.5 Cl1.5 N1 O1' _chemical_formula_weight 461.28 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_h-m 'C 2 2 21 ' _symmetry_space_group_name_hall 'C 2c 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, -z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, -z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 22.212(5) _cell_length_b 11.646(4) _cell_length_c 19.681(4) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 5091(2) _cell_formula_units_z 8 _cell_measurement_temperature 291 _exptl_crystal_density_diffrn 1.20 _diffrn_ambient_temperature 291 _refine_ls_R_factor_obs .0403 _refine_ls_wR_factor_obs .1023 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 .6795(2) .1509(3) .43861(14) .0561(9) Uani d D 1 . N C2 .7137(2) .1851(3) .3819(2) .0427(9) Uani d . 1 . C C3 .6742(2) .2007(3) .3275(2) .0445(9) Uani d . 1 . C C4 .6142(2) .1786(3) .3517(2) .0519(10) Uani d . 1 . C C5 .5578(2) .1806(5) .3235(2) .0781(13) Uani d . 1 . C C6 .5080(2) .1537(6) .3618(2) .107(2) Uani d . 1 . C C7 .5151(2) .1298(5) .4313(2) .100(2) Uani d . 1 . C C8 .5699(2) .1279(4) .4606(2) .0777(14) Uani d . 1 . C C9 .6200(2) .1507(3) .4215(2) .0539(10) Uani d . 1 . C C10 .6984(2) .2346(3) .2644(2) .0450(9) Uani d . 1 . C C11 .75916(15) .2536(3) .2568(2) .0402(9) Uani d . 1 . C C12 .79779(14) .2462(3) .3151(2) .0433(9) Uani d . 1 . C C27 .7738(2) .2078(3) .3765(2) .0479(9) Uani d . 1 . C C23 .86407(15) .2768(3) .3066(2) .0504(10) Uani d . 1 . C C13 .8950(2) .1750(4) .2693(2) .0667(12) Uani d . 1 . C C14 .8564(2) .1096(3) .2194(2) .0554(10) Uani d . 1 . C C15 .82561(15) .1764(3) .16081(15) .0444(9) Uani d . 1 . C C16 .7828(2) .0883(3) .1264(2) .0512(10) Uani d . 1 . C C17 .7449(2) .1418(3) .0699(2) .0554(11) Uani d . 1 . C C18 .7051(2) .2348(3) .0977(2) .0543(10) Uani d . 1 . C C19 .7410(2) .3255(3) .1342(2) .0503(10) Uani d . 1 . C C20 .7890(2) .2846(3) .1875(2) .0437(9) Uani d . 1 . C C21 .8271(2) .3918(3) .2021(2) .0526(9) Uani d . 1 . C C22 .8688(2) .3866(4) .2643(2) .0665(11) Uani d . 1 . C O19 .76893(13) .3894(2) .07916(11) .0622(7) Uani d . 1 . O C28 .8138(2) -.0197(3) .0994(2) .0773(13) Uani d . 1 . C C29 .8751(2) .2130(4) .1105(2) .0619(11) Uani d . 1 . C C24 .89740(15) .2951(4) .3766(2) .0627(11) Uani d . 1 . C C25 .8721(2) .3950(4) .4184(2) .0763(13) Uani d . 1 . C C26 .9654(2) .3116(5) .3675(2) .090(2) Uani d . 1 . C CA .0299(5) .0384(13) -.0171(9) .26(3) Uiso d PG .302(11) . C Cl1A -.0044(8) -.068(2) .0342(10) .300(10) Uani d PGU .302(11) . Cl Cl2A .1092(4) .0223(13) -.0141(12) .318(13) Uani d PGU .302(11) . Cl Cl3A .0048(8) .0233(14) -.1022(9) .318(11) Uani d PGU .302(11) . Cl CB .0420(10) .035(2) .0259(14) .21(3) Uiso d PG .216(11) . C Cl1B .1109(12) .044(3) -.0192(13) .56(3) Uani d PGU .216(11) . Cl Cl2B -.0167(13) -.002(4) -.031(2) .65(4) Uani d PGU .216(11) . Cl Cl3B .0479(18) -.071(3) .0902(19) .43(2) Uani d PGU .216(11) . Cl H1 .6932(16) .149(3) .4783(14) .067 Uiso d D 1 . H H5 .5531(2) .2005(5) .2781(2) .094 Uiso calc R 1 . H H6 .4700(2) .1514(6) .3420(2) .128 Uiso calc R 1 . H H7 .4813(2) .1148(5) .4576(2) .120 Uiso calc R 1 . H H8 .5739(2) .1115(4) .5066(2) .093 Uiso calc R 1 . H H10 .6729(2) .2442(3) .2273(2) .054 Uiso calc R 1 . H H14A .8250(2) .0711(3) .2450(2) .067 Uiso calc R 1 . H H14B .8812(2) .0503(3) .1991(2) .067 Uiso calc R 1 . H H13A .9298(2) .2046(4) .2452(2) .080 Uiso calc R 1 . H H13B .9096(2) .1214(4) .3033(2) .080 Uiso calc R 1 . H H16 .7545(2) .0628(3) .1615(2) .061 Uiso calc R 1 . H H17A .7712(2) .1737(3) .0354(2) .066 Uiso calc R 1 . H H17B .7203(2) .0830(3) .0487(2) .066 Uiso calc R 1 . H H18A .6762(2) .2013(3) .1289(2) .065 Uiso calc R 1 . H H18B .6829(2) .2699(3) .0607(2) .065 Uiso calc R 1 . H H19C .7127(2) .3767(3) .1574(2) .060 Uiso calc R 1 . H H19 .7808(17) .4515(15) .0935(5) .075 Uiso calc R 1 . H H21A .8517(2) .4074(3) .1624(2) .063 Uiso calc R 1 . H H21B .8001(2) .4565(3) .2079(2) .063 Uiso calc R 1 . H H22A .9101(2) .3947(4) .2489(2) .080 Uiso calc R 1 . H H22B .8600(2) .4516(4) .2934(2) .080 Uiso calc R 1 . H H24 .89165(15) .2250(4) .4033(2) .075 Uiso calc R 1 . H H25A .8857(10) .4664(4) .3994(8) .114 Uiso calc R 1 . H H25B .8860(10) .3887(13) .4645(4) .114 Uiso calc R 1 . H H25C .8289(2) .3924(15) .4176(12) .114 Uiso calc R 1 . H H26A .9818(3) .2471(15) .3434(16) .134 Uiso calc R 1 . H H26B .9842(3) .318(3) .4112(2) .134 Uiso calc R 1 . H H26C .9727(2) .3805(17) .3420(15) .134 Uiso calc R 1 . H H27 .7988(2) .1975(3) .4139(2) .057 Uiso calc R 1 . H H28A .8322(12) -.0603(14) .1364(3) .116 Uiso calc R 1 . H H28B .8441(9) .0017(4) .0670(12) .116 Uiso calc R 1 . H H28C .7845(3) -.0682(12) .0778(13) .116 Uiso calc R 1 . H H29A .9028(6) .2636(17) .1329(4) .093 Uiso calc R 1 . H H29B .8571(2) .2520(19) .0727(6) .093 Uiso calc R 1 . H H29C .8962(7) .1463(4) .0947(10) .093 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 O19 .097(2) .062(2) .0271(14) -.013(2) .0068(13) .0079(12) N1 .076(3) .073(2) .019(2) -.018(2) -.002(2) .002(2) C20 .053(2) .054(2) .025(2) -.007(2) .001(2) .000(2) C11 .049(2) .048(2) .024(2) -.001(2) -.001(2) -.004(2) C10 .055(3) .065(2) .015(2) -.005(2) -.003(2) .001(2) C3 .051(2) .055(2) .027(2) -.007(2) -.001(2) -.005(2) C4 .058(3) .071(2) .027(2) -.012(2) -.004(2) -.003(2) C9 .064(3) .072(3) .026(2) -.022(2) .004(2) -.006(2) C2 .057(2) .052(2) .019(2) -.006(2) -.001(2) -.002(2) C27 .060(2) .062(2) .022(2) .003(2) -.008(2) -.004(2) C12 .050(2) .056(2) .024(2) .003(2) -.002(2) -.005(2) C23 .048(2) .071(3) .032(2) .000(2) -.004(2) -.012(2) C13 .063(2) .096(3) .041(2) .016(2) -.005(2) -.018(2) C14 .068(2) .065(2) .033(2) .014(2) -.001(2) -.013(2) C15 .057(2) .053(2) .023(2) -.003(2) .005(2) -.003(2) C22 .067(3) .084(3) .049(2) -.020(2) .000(2) -.011(2) C21 .064(2) .056(2) .037(2) -.003(2) .004(2) -.002(2) C19 .064(2) .059(2) .028(2) .000(2) .005(2) .002(2) C18 .062(2) .072(3) .029(2) -.008(2) -.007(2) .002(2) C17 .076(3) .062(3) .028(2) -.020(2) -.001(2) -.001(2) C16 .069(2) .054(2) .030(2) -.012(2) .001(2) .001(2) C5 .062(3) .136(4) .037(2) -.018(3) .001(2) .000(2) C29 .062(2) .077(3) .046(2) -.007(2) .011(2) -.007(2) C28 .116(4) .059(3) .057(3) -.004(2) -.015(2) -.011(2) C24 .050(2) .098(3) .040(2) .003(2) -.008(2) -.015(2) C26 .062(3) .149(4) .058(3) .001(3) -.009(2) -.035(3) C25 .070(3) .113(4) .046(2) -.001(3) -.007(2) -.036(3) C7 .077(4) .169(5) .052(3) -.050(3) .020(3) -.013(3) C6 .069(3) .202(6) .048(3) -.045(3) .005(2) -.008(3) C8 .086(3) .115(4) .032(2) -.043(3) .009(3) -.012(2) Cl1A .216(12) .233(16) .45(3) -.050(15) .084(17) .000(18) Cl2A .189(9) .105(16) .66(3) -.040(10) .175(17) -.085(18) Cl3A .294(16) .186(12) .48(3) -.034(12) .124(19) -.086(15) Cl1B .44(3) .81(6) .43(4) -.51(4) .25(3) -.44(4) Cl2B .43(3) .90(10) .62(5) -.51(5) .12(5) -.40(7) Cl3B .39(5) .20(2) .71(5) -.02(3) .23(5) .04(4) 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 O19 C19 . 1.453(4) yes N1 C9 . 1.365(5) yes N1 C2 . 1.407(4) yes C20 C21 . 1.537(5) no C20 C11 . 1.559(5) no C20 C19 . 1.569(5) no C20 C15 . 1.589(5) no C11 C10 . 1.375(5) yes C11 C12 . 1.434(5) yes C10 C3 . 1.411(5) yes C3 C2 . 1.394(5) yes C3 C4 . 1.439(5) yes C4 C5 . 1.370(5) yes C4 C9 . 1.417(5) yes C9 C8 . 1.378(5) yes C2 C27 . 1.365(5) yes C27 C12 . 1.394(5) no C12 C23 . 1.524(5) no C23 C22 . 1.530(6) no C23 C13 . 1.555(5) no C23 C24 . 1.577(5) no C13 C14 . 1.512(5) no C14 C15 . 1.549(5) no C15 C29 . 1.539(5) no C15 C16 . 1.555(5) no C22 C21 . 1.536(5) no C19 C18 . 1.506(5) no C18 C17 . 1.501(5) no C17 C16 . 1.527(5) no C16 C28 . 1.528(6) no C5 C6 . 1.375(6) no C24 C25 . 1.532(6) no C24 C26 . 1.533(5) no C7 C8 . 1.347(6) no C7 C6 . 1.404(7) no Cl1A CA . 1.77 ? Cl2A CA . 1.77 ? Cl3A CA . 1.77 ? Cl1B CB . 1.77 ? Cl2B CB . 1.77 ? Cl3B CB . 1.77 ?