data_2200620 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o1120 _journal_page_last o1122 _publ_section_title ; An OBONC five-membered heterocycle ; loop_ _publ_author_name 'Wolfgang Kliegel' 'J\"org Metge' 'Brian O. Patrick' 'Steven J. Rettig' 'James Trotter' _chemical_formula_moiety 'C30 H24 B N O3, C2 H6 O' _chemical_formula_sum 'C32 H30 B N O4 ' _chemical_formula_iupac 'C30 H24 B N O3, C2 H6 O' _chemical_formula_weight 503.40 _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 11.5792(6) _cell_length_b 13.0972(8) _cell_length_c 9.0779(5) _cell_angle_alpha 96.780(5) _cell_angle_beta 93.245(4) _cell_angle_gamma 82.833(4) _cell_volume 1355.18(13) _cell_formula_units_Z 2 _cell_measurement_temperature 294 _exptl_crystal_density_diffrn 1.234 _diffrn_ambient_temperature 294 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_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy O1 .32892(10) .27695(10) .66978(15) .0604(4) Uani d ? . 1.000 O2 .53261(15) .55445(13) .7669(2) .0900(6) Uani d ? . 1.000 O3 .15695(10) .37238(10) .75914(15) .0606(4) Uani d ? . 1.000 O4 .6272(3) .7288(2) .8030(4) .1111(12) Uani d ? . .700 O4a .5797(7) .7307(6) .6482(8) .106(3) Uani d ? . .300 N1 .34582(12) .36503(11) .7649(2) .0463(4) Uani d ? . 1.000 C1 .55368(15) .37424(15) .7090(2) .0495(5) Uani d ? . 1.000 C2 .5859(2) .4688(2) .6879(2) .0612(6) Uani d ? . 1.000 C3 .6734(2) .4776(2) .5903(3) .0722(8) Uani d ? . 1.000 C4 .7313(2) .3920(2) .5195(2) .0704(7) Uani d ? . 1.000 C5 .7052(2) .2918(2) .5392(2) .0598(6) Uani d ? . 1.000 C6 .7694(2) .2019(2) .4702(3) .0780(8) Uani d ? . 1.000 C7 .7460(2) .1068(2) .4927(3) .0929(10) Uani d ? . 1.000 C8 .6569(2) .0972(2) .5850(3) .0872(9) Uani d ? . 1.000 C9 .5925(2) .1821(2) .6535(3) .0671(7) Uani d ? . 1.000 C10 .6147(2) .2828(2) .6349(2) .0529(6) Uani d ? . 1.000 C11 .46600(15) .37034(14) .8233(2) .0496(5) Uani d ? . 1.000 C12 .24801(15) .41491(14) .8113(2) .0469(5) Uani d ? . 1.000 C13 .23238(15) .51235(14) .9101(2) .0464(5) Uani d ? . 1.000 C14 .1573(2) .5200(2) 1.0253(2) .0588(6) Uani d ? . 1.000 C15 .1336(2) .6122(2) 1.1145(2) .0700(7) Uani d ? . 1.000 C16 .1843(2) .6972(2) 1.0879(3) .0693(7) Uani d ? . 1.000 C17 .2575(2) .6906(2) .9733(3) .0678(7) Uani d ? . 1.000 C18 .2829(2) .59853(15) .8840(2) .0576(6) Uani d ? . 1.000 C19 .14490(15) .27566(14) .4953(2) .0518(5) Uani d ? . 1.000 C20 .0864(2) .3651(2) .4456(3) .0694(7) Uani d ? . 1.000 C21 .0431(2) .3685(2) .3003(4) .0913(10) Uani d ? . 1.000 C22 .0592(2) .2828(3) .2003(3) .0906(10) Uani d ? . 1.000 C23 .1157(3) .1926(2) .2441(3) .0886(9) Uani d ? . 1.000 C24 .1575(2) .1890(2) .3903(3) .0711(7) Uani d ? . 1.000 C25 .1670(2) .17198(15) .7359(2) .0536(6) Uani d ? . 1.000 C26 .2456(2) .1184(2) .8300(3) .0744(8) Uani d ? . 1.000 C27 .2175(3) .0329(2) .8920(3) .0874(9) Uani d ? . 1.000 C28 .1113(3) -.0007(2) .8628(3) .0841(9) Uani d ? . 1.000 C29 .0317(2) .0506(2) .7724(3) .0809(9) Uani d ? . 1.000 C30 .0597(2) .1353(2) .7094(3) .0651(7) Uani d ? . 1.000 C31 .5456(6) .8085(4) .7204(6) .110(2) Uani d ? . .750 C31a .600(2) .821(2) .779(3) .107(7) Uiso d ? . .160 C31b .457(4) .800(4) .798(6) .114(12) Uiso d ? . .090 C32 .5216(6) .8964(5) .8174(8) .155(3) Uani d ? . .700 C32a .511(2) .8248(12) .841(2) .162(8) Uani d ? . .300 B1 .1972(2) .2694(2) .6602(3) .0531(6) Uani d ? . 1.000 H1 .561(3) .609(3) .761(4) .160(11) Uiso d ? . 1.000 H2 .6921 .5462 .5738 .087 Uiso c ? . 1.000 H3 .7929 .3991 .4529 .085 Uiso c ? . 1.000 H4 .8318 .2087 .4048 .094 Uiso c ? . 1.000 H5 .7913 .0449 .4444 .111 Uiso c ? . 1.000 H6 .6401 .0280 .6012 .105 Uiso c ? . 1.000 H7 .5296 .1728 .7168 .081 Uiso c ? . 1.000 H8 .4667 .4328 .8942 .059 Uiso c ? . 1.000 H9 .4901 .3090 .8748 .059 Uiso c ? . 1.000 H10 .1207 .4594 1.0437 .071 Uiso c ? . 1.000 H11 .0809 .6171 1.1963 .084 Uiso c ? . 1.000 H12 .1680 .7628 1.1513 .083 Uiso c ? . 1.000 H13 .2923 .7520 .9543 .081 Uiso c ? . 1.000 H14 .3363 .5942 .8028 .069 Uiso c ? . 1.000 H15 .0753 .4282 .5156 .083 Uiso c ? . 1.000 H16 .0009 .4328 .2699 .110 Uiso c ? . 1.000 H17 .0304 .2856 .0970 .109 Uiso c ? . 1.000 H18 .1268 .1304 .1725 .106 Uiso c ? . 1.000 H19 .1971 .1236 .4202 .085 Uiso c ? . 1.000 H20 .3226 .1415 .8531 .089 Uiso c ? . 1.000 H21 .2748 -.0034 .9572 .105 Uiso c ? . 1.000 H22 .0920 -.0611 .9063 .101 Uiso c ? . 1.000 H23 -.0455 .0275 .7520 .097 Uiso c ? . 1.000 H24 .0015 .1705 .6439 .078 Uiso c ? . 1.000 H25 .5841 .8251 .6344 .132 Uiso d ? . .750 H26 .4731 .7798 .6871 .132 Uiso d ? . .750 H27 .5836 .9408 .8162 .186 Uiso d ? . .700 H28 .4470 .9339 .7873 .186 Uiso d ? . .700 H29 .5170 .8772 .9178 .186 Uiso d ? . .700 H30 .6987 .7297 .7791 .133 Uiso d ? . .700 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 .0437(7) .0580(8) .0740(9) -.0105(6) .0073(6) -.0227(7) O2 .0707(11) .0579(10) .144(2) -.0194(8) .0431(10) -.0097(10) O3 .0406(7) .0584(8) .0782(10) -.0108(6) .0087(6) -.0200(7) O4 .092(2) .074(2) .174(3) -.0334(15) -.003(2) .021(2) O4a .126(6) .091(5) .111(5) -.043(4) .017(5) .011(4) N1 .0407(8) .0481(8) .0489(8) -.0104(6) .0058(6) -.0074(7) C1 .0386(10) .0577(11) .0517(10) -.0093(8) .0026(8) -.0003(9) C2 .0456(11) .0628(13) .0752(14) -.0120(9) .0116(10) -.0019(11) C3 .0563(13) .0764(15) .089(2) -.0181(11) .0144(12) .0145(13) C4 .0527(13) .098(2) .0635(14) -.0155(12) .0129(10) .0086(12) C5 .0470(11) .0803(15) .0493(11) -.0059(10) .0048(9) -.0035(10) C6 .0633(14) .100(2) .0643(14) .0033(13) .0149(11) -.0093(13) C7 .087(2) .086(2) .095(2) .0171(15) .0246(15) -.0147(15) C8 .082(2) .0654(15) .109(2) .0055(13) .0191(15) -.0027(14) C9 .0607(13) .0632(13) .0756(15) -.0017(10) .0103(11) .0023(11) C10 .0422(10) .0638(12) .0505(11) -.0059(9) -.0002(8) -.0010(9) C11 .0408(10) .0578(11) .0488(10) -.0087(8) .0018(8) -.0023(8) C12 .0419(10) .0502(10) .0487(10) -.0098(8) .0072(8) -.0021(8) C13 .0411(9) .0501(10) .0460(10) -.0056(8) .0025(8) -.0029(8) C14 .0586(12) .0651(13) .0524(11) -.0088(10) .0124(9) -.0009(10) C15 .0610(13) .090(2) .0529(12) -.0016(12) .0107(10) -.0145(11) C16 .0572(13) .0685(14) .0712(14) .0021(11) -.0061(11) -.0239(11) C17 .0600(13) .0504(12) .090(2) -.0098(10) .0001(12) -.0078(11) C18 .0510(11) .0553(11) .0661(13) -.0101(9) .0096(9) -.0021(10) C19 .0437(10) .0463(10) .0667(12) -.0125(8) .0056(9) .0029(9) C20 .0609(13) .0613(13) .087(2) -.0024(10) .0134(12) .0140(12) C21 .073(2) .105(2) .101(2) .0012(15) .0036(15) .044(2) C22 .082(2) .125(3) .075(2) -.037(2) -.0150(14) .038(2) C23 .120(2) .089(2) .0626(15) -.045(2) -.0049(14) -.0006(13) C24 .098(2) .0523(12) .0622(13) -.0163(11) -.0053(12) .0018(10) C25 .0531(11) .0542(11) .0511(11) -.0066(9) .0091(9) -.0082(9) C26 .0715(15) .082(2) .0700(15) -.0161(12) -.0076(12) .0067(12) C27 .102(2) .090(2) .070(2) -.004(2) .0011(14) .0205(14) C28 .100(2) .079(2) .077(2) -.0079(15) .0321(15) .0145(13) C29 .071(2) .078(2) .100(2) -.0189(13) .0227(14) .0128(14) C30 .0534(12) .0671(13) .0771(15) -.0118(10) .0102(10) .0094(11) C31 .124(4) .106(4) .096(4) -.020(3) -.004(3) -.010(3) C32 .137(5) .128(5) .181(6) .016(4) -.018(4) -.017(5) C32a .25(2) .090(10) .16(2) -.086(13) .068(14) -.034(10) B1 .0418(11) .0479(12) .0663(14) -.0073(9) .0062(10) -.0109(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 N1 . . 1.384(2) yes O1 B1 . . 1.537(2) yes O2 C2 . . 1.357(2) yes O2 H1 . . .83(3) no O3 C12 . . 1.294(2) yes O3 B1 . . 1.564(2) yes O4 C31 . . 1.551(6) no O4 H30 . . .87 no O4a C31a . . 1.61(3) no N1 C11 . . 1.468(2) yes N1 C12 . . 1.301(2) yes C1 C2 . . 1.374(3) yes C1 C10 . . 1.428(3) yes C1 C11 . . 1.502(2) yes C2 C3 . . 1.407(3) yes C3 C4 . . 1.346(3) yes C3 H2 . . .98 no C4 C5 . . 1.417(3) yes C4 H3 . . .98 no C5 C6 . . 1.411(3) yes C5 C10 . . 1.423(3) yes C6 C7 . . 1.348(4) yes C6 H4 . . .98 no C7 C8 . . 1.392(4) yes C7 H5 . . .98 no C8 C9 . . 1.365(3) yes C8 H6 . . .98 no C9 C10 . . 1.405(3) yes C9 H7 . . .98 no C11 H8 . . .98 no C11 H9 . . .98 no C12 C13 . . 1.468(2) yes C13 C14 . . 1.385(2) yes C13 C18 . . 1.385(3) yes C14 C15 . . 1.379(3) yes C14 H10 . . .98 no C15 C16 . . 1.372(3) yes C15 H11 . . .98 no C16 C17 . . 1.367(3) yes C16 H12 . . .98 no C17 C18 . . 1.381(3) yes C17 H13 . . .98 no C18 H14 . . .98 no C19 C20 . . 1.389(3) yes C19 C24 . . 1.392(3) yes C19 B1 . . 1.590(3) yes C20 C21 . . 1.388(4) yes C20 H15 . . .98 no C21 C22 . . 1.359(4) yes C21 H16 . . .98 no C22 C23 . . 1.368(4) yes C22 H17 . . .98 no C23 C24 . . 1.391(3) yes C23 H18 . . .98 no C24 H19 . . .98 no C25 C26 . . 1.395(3) yes C25 C30 . . 1.386(3) yes C25 B1 . . 1.602(3) yes C26 C27 . . 1.391(3) yes C26 H20 . . .98 no C27 C28 . . 1.360(4) yes C27 H21 . . .98 no C28 C29 . . 1.365(4) yes C28 H22 . . .98 no C29 C30 . . 1.387(3) yes C29 H23 . . .98 no C30 H24 . . .98 no C31 C32 . . 1.373(8) no C31 H25 . . .98 no C31 H26 . . .98 no C31a C32a . . 1.19(3) no C32 H27 . . .98 no C32 H28 . . .98 no C32 H29 . . .98 no