#------------------------------------------------------------------------------ #$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012550.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_2012550 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2002 _journal_volume 58 _journal_page_first o168 _journal_page_last o169 _publ_section_title ; 5-Butyl-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-3- (2,4,6-trimethylphenyl)isoxazole ; loop_ _publ_author_name 'Harrity, Joseph P. A.' 'Adams, Harry' 'Davies, Mark W.' 'Wybrow, Robert A.J.' 'Johnson, Christopher N.' _chemical_formula_moiety 'C22 H32 B N O3' _chemical_formula_sum 'C22 H32 B N O3' _chemical_formula_iupac 'C22 H32 B N O3' _chemical_formula_weight 369.30 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.132(6) _cell_length_b 9.9664(18) _cell_length_c 27.505(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.331(4) _cell_angle_gamma 90.00 _cell_volume 8759(3) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.120 _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 B1 .18860(14) .4803(5) .67222(18) .0325(12) Uani d . 1 . . B O1 .15931(8) .1987(3) .74555(10) .0431(8) Uani d . 1 . . O O2 .19963(8) .4903(2) .62788(9) .0338(7) Uani d . 1 . . O O3 .19014(8) .6005(2) .69723(9) .0380(7) Uani d . 1 . . O N2 .16948(10) .1224(3) .70690(13) .0422(9) Uani d . 1 . . N C1 .19545(13) .7055(4) .66187(15) .0348(11) Uani d . 1 . . C C2 .21588(13) .6264(4) .62582(15) .0334(10) Uani d . 1 . . C C3 .17970(12) .2105(4) .67698(16) .0348(11) Uani d . 1 . . C C4 .17727(12) .3469(4) .69395(15) .0308(10) Uani d . 1 . . C C5 .16448(12) .3315(4) .73686(15) .0328(10) Uani d . 1 . . C C6 .19009(13) .1607(4) .63104(16) .0318(10) Uani d . 1 . . C C7 .15795(13) .1130(4) .59088(16) .0352(11) Uani d . 1 . . C C8 .16813(13) .0652(4) .54825(16) .0383(11) Uani d . 1 . . C H8A .1464 .0330 .5208 .046 Uiso calc R 1 . . H C9 .20874(14) .0630(4) .54439(17) .0397(12) Uani d . 1 . . C C10 .24014(13) .1103(4) .58483(17) .0379(11) Uani d . 1 . . C H10A .2683 .1091 .5827 .045 Uiso calc R 1 . . H C11 .23164(13) .1589(4) .62793(16) .0334(10) Uani d . 1 . . C C12 .26644(12) .2081(4) .67125(16) .0451(12) Uani d . 1 . . C H12A .2932 .2006 .6625 .068 Uiso calc R 1 . . H H12B .2674 .1535 .7012 .068 Uiso calc R 1 . . H H12C .2614 .3021 .6783 .068 Uiso calc R 1 . . H C13 .11276(12) .1116(4) .59272(16) .0417(12) Uani d . 1 . . C H13A .0952 .0747 .5611 .063 Uiso calc R 1 . . H H13B .1037 .2034 .5972 .063 Uiso calc R 1 . . H H13C .1100 .0559 .6210 .063 Uiso calc R 1 . . H C14 .21890(14) .0124(4) .49704(17) .0580(14) Uani d . 1 . . C H14A .1931 -.0163 .4726 .087 Uiso calc R 1 . . H H14B .2382 -.0638 .5055 .087 Uiso calc R 1 . . H H14C .2320 .0844 .4824 .087 Uiso calc R 1 . . H C15 .20384(13) .6759(4) .57210(15) .0483(13) Uani d . 1 . . C H15A .2178 .6210 .5518 .072 Uiso calc R 1 . . H H15B .2125 .7697 .5712 .072 Uiso calc R 1 . . H H15C .1734 .6691 .5584 .072 Uiso calc R 1 . . H C16 .26320(12) .6143(4) .64494(17) .0518(13) Uani d . 1 . . C H16A .2740 .5634 .6206 .078 Uiso calc R 1 . . H H16B .2704 .5676 .6775 .078 Uiso calc R 1 . . H H16C .2757 .7041 .6491 .078 Uiso calc R 1 . . H C17 .22254(14) .8163(4) .69176(16) .0492(13) Uani d . 1 . . C H17A .2074 .8607 .7134 .074 Uiso calc R 1 . . H H17B .2291 .8821 .6685 .074 Uiso calc R 1 . . H H17C .2486 .7777 .7126 .074 Uiso calc R 1 . . H C18 .15211(13) .7581(4) .63646(16) .0460(12) Uani d . 1 . . C H18A .1411 .8070 .6611 .069 Uiso calc R 1 . . H H18B .1335 .6827 .6229 .069 Uiso calc R 1 . . H H18C .1536 .8185 .6089 .069 Uiso calc R 1 . . H C19 .15366(12) .4230(4) .77390(15) .0382(11) Uani d . 1 A . C H19A .1562 .5169 .7633 .046 Uiso calc R 1 . . H H19B .1740 .4099 .8071 .046 Uiso calc R 1 . . H C20 .10990(15) .4010(5) .77929(18) .0580(14) Uani d D 1 . . C H20A .1062 .4471 .8097 .070 Uiso calc PR .512(9) A 1 H H20B .1044 .3040 .7821 .070 Uiso calc PR .512(9) A 1 H H20C .1108 .3179 .7993 .070 Uiso d PR .488(9) A 2 H H20D .1037 .4754 .8000 .070 Uiso d PR .488(9) A 2 H C21A .0799(2) .4610(14) .7309(3) .059(4) Uani d PDU .512(9) A 1 C H21A .0911 .5494 .7244 .070 Uiso calc PR .512(9) A 1 H H21B .0806 .4020 .7021 .070 Uiso calc PR .512(9) A 1 H C21B .0712(3) .3846(9) .7332(4) .066(4) Uani d PDU .488(9) A 2 C H21C .0773 .3239 .7076 .079 Uiso calc PR .488(9) A 2 H H21D .0467 .3502 .7435 .079 Uiso calc PR .488(9) A 2 H C22A .0347(3) .4796(12) .7312(5) .087(5) Uani d PDU .512(9) A 1 C H22A .0192 .5204 .6994 .130 Uiso calc PR .512(9) A 1 H H22B .0333 .5382 .7593 .130 Uiso calc PR .512(9) A 1 H H22C .0224 .3922 .7352 .130 Uiso calc PR .512(9) A 1 H C22B .0643(4) .5269(10) .7140(5) .060(4) Uani d PDU .488(9) A 2 C H22D .0404 .5295 .6841 .091 Uiso calc PR .488(9) A 2 H H22E .0894 .5590 .7053 .091 Uiso calc PR .488(9) A 2 H H22F .0586 .5845 .7403 .091 Uiso calc PR .488(9) A 2 H B1A .08846(15) .0006(5) .40110(18) .0344(12) Uani d . 1 . . B N2A .11705(11) .3561(3) .37449(13) .0454(10) Uani d . 1 . . N O1A .12632(9) .2805(3) .33470(11) .0509(9) Uani d . 1 . . O O2A .08039(8) -.0109(2) .44728(10) .0375(7) Uani d . 1 . . O O3A .08283(8) -.1170(3) .37447(10) .0414(8) Uani d . 1 . . O C1A .07694(14) -.2228(4) .40897(16) .0396(11) Uani d . 1 . . C C2A .06054(13) -.1418(4) .44826(15) .0370(11) Uani d . 1 . . C C3A .10346(12) .2667(4) .40129(16) .0358(11) Uani d . 1 . . C C4A .10266(12) .1326(4) .38154(16) .0340(10) Uani d . 1 . . C C5A .11766(13) .1497(4) .34067(17) .0420(12) Uani d . 1 . . C C6A .09173(13) .3156(4) .44646(15) .0317(10) Uani d . 1 . . C C7A .12315(13) .3626(4) .48839(16) .0354(11) Uani d . 1 . . C C8A .11199(13) .4091(4) .53059(16) .0365(11) Uani d . 1 . . C H8AA .1331 .4416 .5586 .044 Uiso calc R 1 . . H C9A .07087(14) .4093(4) .53289(16) .0346(11) Uani d . 1 . . C C10A .04017(13) .3637(4) .49119(15) .0352(11) Uani d . 1 . . C H10B .0117 .3653 .4922 .042 Uiso calc R 1 . . H C11A .04974(13) .3162(4) .44841(16) .0337(11) Uani d . 1 . . C C12A .01548(13) .2680(4) .40371(15) .0459(12) Uani d . 1 . . C H12D -.0117 .2758 .4114 .069 Uiso calc R 1 . . H H12E .0205 .1740 .3966 .069 Uiso calc R 1 . . H H12F .0154 .3230 .3742 .069 Uiso calc R 1 . . H C13A .16866(12) .3660(4) .48762(17) .0463(12) Uani d . 1 . . C H13D .1857 .4015 .5197 .069 Uiso calc R 1 . . H H13E .1718 .4238 .4600 .069 Uiso calc R 1 . . H H13F .1780 .2750 .4826 .069 Uiso calc R 1 . . H C14A .05952(13) .4571(4) .57979(15) .0464(12) Uani d . 1 . . C H14D .0292 .4512 .5746 .070 Uiso calc R 1 . . H H14E .0685 .5505 .5867 .070 Uiso calc R 1 . . H H14F .0736 .4007 .6085 .070 Uiso calc R 1 . . H C15A .01384(12) -.1174(4) .43315(16) .0461(12) Uani d . 1 . . C H15D .0053 -.0833 .3985 .069 Uiso calc R 1 . . H H15E .0067 -.0513 .4560 .069 Uiso calc R 1 . . H H15F -.0008 -.2017 .4352 .069 Uiso calc R 1 . . H C16A .07476(14) -.1969(4) .50189(15) .0519(13) Uani d . 1 . . C H16D .0635 -.1408 .5244 .078 Uiso calc R 1 . . H H16E .1054 -.1964 .5132 .078 Uiso calc R 1 . . H H16F .0646 -.2890 .5025 .078 Uiso calc R 1 . . H C17A .11966(14) -.2872(4) .43053(18) .0599(14) Uani d . 1 . . C H17D .1278 -.3370 .4039 .090 Uiso calc R 1 . . H H17E .1182 -.3489 .4578 .090 Uiso calc R 1 . . H H17F .1404 -.2172 .4438 .090 Uiso calc R 1 . . H C18A .04637(14) -.3259(4) .37939(16) .0527(13) Uani d . 1 . . C H18D .0190 -.2837 .3659 .079 Uiso calc R 1 . . H H18E .0437 -.4001 .4017 .079 Uiso calc R 1 . . H H18F .0567 -.3602 .3515 .079 Uiso calc R 1 . . H C19A .12705(15) .0590(4) .30167(17) .0518(13) Uani d . 1 B . C H19C .1197 -.0341 .3084 .062 Uiso calc R 1 . . H H19D .1575 .0615 .3048 .062 Uiso calc R 1 . . H C20A .10384(17) .0959(6) .2484(2) .0808(18) Uani d D 1 . . C H20W .1224 .1648 .2398 .097 Uiso calc PR .327(13) B 1 H H20X .1079 .0152 .2292 .097 Uiso calc PR .327(13) B 1 H H20Y .1157 .0500 .2234 .097 Uiso d PR .673(13) B 2 H H20Z .1044 .1941 .2430 .097 Uiso d PR .673(13) B 2 H C21 .0612(5) .1429(17) .2192(13) .227(16) Uiso d PDU .327(13) B 1 C H21E .0639 .2007 .1910 .272 Uiso calc PR .327(13) B 1 H H21H .0485 .1971 .2415 .272 Uiso calc PR .327(13) B 1 H C21' .0574(2) .0737(10) .2370(4) .086(4) Uiso d PDU .673(13) B 2 C H21F .0435 .1327 .2085 .103 Uiso calc PR .673(13) B 2 H H21G .0480 .1022 .2667 .103 Uiso calc PR .673(13) B 2 H C22 .0331(5) .0256(19) .1988(7) .075(7) Uiso d PDU .327(13) B 1 C H22G .0039 .0554 .1894 .112 Uiso calc PR .327(13) B 1 H H22H .0368 -.0443 .2247 .112 Uiso calc PR .327(13) B 1 H H22I .0403 -.0106 .1690 .112 Uiso calc PR .327(13) B 1 H C22' .0427(4) -.0677(10) .2239(5) .146(5) Uiso d PDU .673(13) B 2 C H22J .0133 -.0757 .2244 .219 Uiso calc PR .673(13) B 2 H H22K .0598 -.1297 .2486 .219 Uiso calc PR .673(13) B 2 H H22L .0454 -.0900 .1902 .219 Uiso calc PR .673(13) B 2 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 B1 .030(3) .036(3) .030(3) .003(2) .005(2) -.005(2) O1 .059(2) .0339(18) .0467(19) .0006(15) .0329(16) .0056(15) O2 .0476(19) .0243(15) .0333(18) -.0015(13) .0172(14) -.0014(13) O3 .059(2) .0289(16) .0299(17) -.0009(14) .0190(15) .0004(14) N2 .062(3) .029(2) .045(2) -.0007(18) .032(2) -.0014(18) C1 .044(3) .027(2) .038(3) .000(2) .019(2) .002(2) C2 .042(3) .024(2) .038(3) -.002(2) .017(2) .000(2) C3 .036(3) .030(2) .042(3) .003(2) .016(2) .004(2) C4 .039(3) .023(2) .029(3) .0026(19) .008(2) .0033(19) C5 .043(3) .021(2) .034(3) .0005(19) .010(2) .005(2) C6 .041(3) .021(2) .035(3) .003(2) .013(2) .003(2) C7 .043(3) .022(2) .044(3) .000(2) .016(2) .006(2) C8 .047(3) .030(2) .040(3) -.002(2) .013(2) .000(2) C9 .050(3) .034(3) .043(3) .001(2) .026(3) -.001(2) C10 .031(3) .034(2) .053(3) .003(2) .020(2) .002(2) C11 .038(3) .026(2) .040(3) -.001(2) .017(2) .004(2) C12 .043(3) .043(3) .054(3) .003(2) .020(3) .002(2) C13 .042(3) .035(3) .051(3) .001(2) .018(2) .001(2) C14 .078(4) .050(3) .058(3) -.005(3) .037(3) -.011(3) C15 .077(4) .033(3) .041(3) -.001(2) .027(3) .004(2) C16 .047(3) .044(3) .071(4) -.004(2) .027(3) -.001(3) C17 .073(4) .027(2) .048(3) -.008(2) .017(3) -.005(2) C18 .050(3) .039(3) .054(3) .009(2) .023(2) .007(2) C19 .048(3) .033(2) .036(3) -.002(2) .016(2) .003(2) C20 .064(4) .069(3) .052(3) -.007(3) .034(3) -.020(3) C21A .033(7) .082(12) .053(9) -.012(8) -.003(7) -.030(9) C21B .052(9) .053(7) .098(10) -.024(6) .028(7) -.039(7) C22A .055(7) .099(10) .106(10) .008(7) .021(7) -.014(8) C22B .045(10) .089(9) .044(8) .002(7) .005(7) .003(6) B1A .040(3) .033(3) .032(3) .003(2) .013(3) .004(2) N2A .070(3) .033(2) .042(2) -.0019(19) .031(2) .0016(18) O1A .082(2) .0329(18) .053(2) -.0020(16) .0444(18) -.0003(15) O2A .053(2) .0279(16) .0329(18) -.0070(14) .0141(15) .0014(13) O3A .059(2) .0278(16) .0452(19) -.0050(14) .0275(16) .0002(14) C1A .056(3) .025(2) .042(3) -.003(2) .021(2) .007(2) C2A .052(3) .025(2) .037(3) -.007(2) .017(2) .004(2) C3A .038(3) .033(3) .039(3) -.002(2) .013(2) .005(2) C4A .038(3) .027(2) .041(3) .0063(19) .017(2) .004(2) C5A .059(3) .023(2) .055(3) -.002(2) .032(3) -.001(2) C6A .045(3) .021(2) .032(3) -.001(2) .016(2) .0008(19) C7A .042(3) .026(2) .040(3) -.001(2) .014(2) .004(2) C8A .041(3) .032(2) .036(3) -.004(2) .010(2) -.002(2) C9A .046(3) .025(2) .033(3) -.001(2) .012(2) .003(2) C10A .037(3) .030(2) .042(3) .001(2) .016(2) .003(2) C11A .041(3) .024(2) .036(3) .003(2) .011(2) .003(2) C12A .050(3) .043(3) .044(3) .008(2) .012(2) -.005(2) C13A .041(3) .039(3) .063(3) .000(2) .021(2) .008(2) C14A .053(3) .049(3) .040(3) .010(2) .017(2) -.004(2) C15A .048(3) .043(3) .054(3) -.005(2) .025(2) .002(2) C16A .079(4) .037(3) .042(3) -.006(2) .020(3) .012(2) C17A .068(4) .034(3) .084(4) .003(3) .031(3) .010(3) C18A .073(4) .039(3) .054(3) -.018(3) .031(3) -.012(2) C19A .073(4) .035(3) .061(4) .000(2) .041(3) .000(2) C20A .093(5) .090(4) .066(4) .027(4) .033(3) -.018(3) 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 B1 O2 . 1.366(5) ? B1 O3 . 1.376(5) ? B1 C4 . 1.544(6) y O1 C5 . 1.364(4) y O1 N2 . 1.418(4) y O2 C2 . 1.465(4) ? O3 C1 . 1.470(4) ? N2 C3 . 1.308(5) ? C1 C18 . 1.515(5) ? C1 C17 . 1.521(5) ? C1 C2 . 1.555(5) ? C2 C15 . 1.508(5) ? C2 C16 . 1.521(5) ? C3 C4 . 1.446(5) y C3 C6 . 1.481(5) y C4 C5 . 1.364(5) y C5 C19 . 1.480(5) y C6 C7 . 1.399(5) ? C6 C11 . 1.402(5) ? C7 C8 . 1.387(5) ? C7 C13 . 1.512(5) ? C8 C9 . 1.378(5) ? C8 H8A . .9500 ? C9 C10 . 1.389(5) ? C9 C14 . 1.515(5) ? C10 C11 . 1.377(5) ? C10 H10A . .9500 ? C11 C12 . 1.504(5) ? C12 H12A . .9800 ? C12 H12B . .9800 ? C12 H12C . .9800 ? C13 H13A . .9800 ? C13 H13B . .9800 ? C13 H13C . .9800 ? C14 H14A . .9800 ? C14 H14B . .9800 ? C14 H14C . .9800 ? C15 H15A . .9800 ? C15 H15B . .9800 ? C15 H15C . .9800 ? C16 H16A . .9800 ? C16 H16B . .9800 ? C16 H16C . .9800 ? C17 H17A . .9800 ? C17 H17B . .9800 ? C17 H17C . .9800 ? C18 H18A . .9800 ? C18 H18B . .9800 ? C18 H18C . .9800 ? C19 C20 . 1.512(5) ? C19 H19A . .9900 ? C19 H19B . .9900 ? C20 C21B . 1.554(7) ? C20 C21A . 1.556(7) ? C20 H20A . .9900 ? C20 H20B . .9900 ? C20 H20C . .9899 ? C20 H20D . .9899 ? C21A C22A . 1.511(2) ? C21A H21A . .9900 ? C21A H21B . .9900 ? C21B C22B . 1.510(2) ? C21B H21C . .9900 ? C21B H21D . .9900 ? C22A H22A . .9800 ? C22A H22B . .9800 ? C22A H22C . .9800 ? C22B H22D . .9800 ? C22B H22E . .9800 ? C22B H22F . .9800 ? B1A O3A . 1.369(5) ? B1A O2A . 1.370(5) ? B1A C4A . 1.541(6) y N2A C3A . 1.310(5) y N2A O1A . 1.427(4) y O1A C5A . 1.354(4) y O2A C2A . 1.465(4) ? O3A C1A . 1.466(4) ? C1A C18A . 1.519(5) ? C1A C17A . 1.524(5) ? C1A C2A . 1.558(5) ? C2A C15A . 1.512(5) ? C2A C16A . 1.527(5) ? C3A C4A . 1.441(5) y C3A C6A . 1.479(5) y C4A C5A . 1.355(5) y C5A C19A . 1.497(5) y C6A C11A . 1.406(5) ? C6A C7A . 1.414(5) ? C7A C8A . 1.388(5) ? C7A C13A . 1.514(5) ? C8A C9A . 1.380(5) ? C8A H8AA . .9500 ? C9A C10A . 1.393(5) ? C9A C14A . 1.513(5) ? C10A C11A . 1.381(5) ? C10A H10B . .9500 ? C11A C12A . 1.514(5) ? C12A H12D . .9800 ? C12A H12E . .9800 ? C12A H12F . .9800 ? C13A H13D . .9800 ? C13A H13E . .9800 ? C13A H13F . .9800 ? C14A H14D . .9800 ? C14A H14E . .9800 ? C14A H14F . .9800 ? C15A H15D . .9800 ? C15A H15E . .9800 ? C15A H15F . .9800 ? C16A H16D . .9800 ? C16A H16E . .9800 ? C16A H16F . .9800 ? C17A H17D . .9800 ? C17A H17E . .9800 ? C17A H17F . .9800 ? C18A H18D . .9800 ? C18A H18E . .9800 ? C18A H18F . .9800 ? C19A C20A . 1.510(6) ? C19A H19C . .9900 ? C19A H19D . .9900 ? C20A C21 . 1.503(8) ? C20A C21' . 1.503(8) ? C20A H20W . .9900 ? C20A H20X . .9900 ? C20A H20Y . .9899 ? C20A H20Z . .9900 ? C21 C22 . 1.508(2) ? C21 H20Z . 1.4963 ? C21 H21E . .9900 ? C21 H21H . .9900 ? C21' C22' . 1.504(2) ? C21' H21F . .9900 ? C21' H21G . .9900 ? C22 H22G . .9800 ? C22 H22H . .9800 ? C22 H22I . .9800 ? C22' H22J . .9800 ? C22' H22K . .9800 ? C22' H22L . .9800 ?