#------------------------------------------------------------------------------ #$Date: 2008-01-26 14:05:32 +0100 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2009098.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_2009098 _journal_name_full 'Acta Crystallographica' _journal_year 1999 _journal_volume C55 _journal_page_first 1885 _journal_page_last 1888 _publ_section_title ; 1:1 Adducts of 4-picoline with methylcatecholborane and phenylcatecholborane ; loop_ _publ_author_name 'Clegg, William' 'Scott, Andrew J.' "Souza, F\'abio E.S." 'Marder, Todd B.' _chemical_formula_sum 'C13 H14 B N O2' _chemical_formula_weight 227.06 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.3206(7) _cell_length_b 15.6683(7) _cell_length_c 19.3267(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4942.1(4) _cell_formula_units_Z 16 _cell_measurement_temperature 160(2) _exptl_crystal_density_diffrn 1.221 _diffrn_ambient_temperature 160(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 .09583(10) .86405(10) .44047(9) .0322(3) Uani d . 1 . . B O1 .02459(6) .92126(6) .43013(5) .0326(2) Uani d . 1 . . O O2 .08036(6) .78869(6) .39694(5) .0338(2) Uani d . 1 . . O C1 -.03377(8) .87127(8) .39964(7) .0289(3) Uani d . 1 . . C C2 -.00085(9) .79249(9) .38063(7) .0291(3) Uani d . 1 . . C C3 -.04809(10) .73045(9) .35000(7) .0354(3) Uani d . 1 . . C H3 -.0255 .6768 .3374 .042 Uiso calc R 1 . . H C4 -.13038(10) .74912(10) .33811(8) .0404(4) Uani d . 1 . . C H4 -.1648 .7071 .3178 .048 Uiso calc R 1 . . H C5 -.16278(10) .82778(11) .35530(8) .0415(4) Uani d . 1 . . C H5 -.2187 .8395 .3456 .050 Uiso calc R 1 . . H C6 -.11440(9) .89051(10) .38682(8) .0361(3) Uani d . 1 . . C H6 -.1366 .9445 .3989 .043 Uiso calc R 1 . . H C7 .18374(10) .90628(11) .43273(10) .0467(4) Uani d . 1 . . C H7A .1877 .9559 .4634 .070 Uiso calc R 1 . . H H7B .1919 .9245 .3847 .070 Uiso calc R 1 . . H H7C .2259 .8645 .4452 .070 Uiso calc R 1 . . H N1 .08891(7) .82868(7) .52125(6) .0282(2) Uani d . 1 . . N C8 .11399(9) .74935(9) .53656(8) .0340(3) Uani d . 1 . . C H8 .1274 .7114 .4999 .041 Uiso calc R 1 . . H C9 .12091(9) .72130(10) .60382(8) .0380(3) Uani d . 1 . . C H9 .1374 .6642 .6129 .046 Uiso calc R 1 . . H C10 .10397(9) .77589(11) .65821(8) .0395(4) Uani d . 1 . . C C11 .07534(9) .85705(11) .64142(8) .0410(4) Uani d . 1 . . C H11 .0608 .8958 .6772 .049 Uiso calc R 1 . . H C12 .06796(9) .88130(9) .57331(8) .0333(3) Uani d . 1 . . C H12 .0476 .9366 .5628 .040 Uiso calc R 1 . . H C13 .11630(13) .74780(16) .73168(9) .0648(6) Uani d . 1 . . C H13A .1700 .7203 .7362 .097 Uiso calc R 1 . . H H13B .0732 .7072 .7445 .097 Uiso calc R 1 . . H H13C .1138 .7975 .7623 .097 Uiso calc R 1 . . H B2 -.04752(10) -.00037(10) .12535(8) .0302(3) Uani d . 1 . . B O3 -.02752(6) .00784(6) .19977(5) .0312(2) Uani d . 1 . . O O4 .03126(6) .01225(6) .08812(5) .0323(2) Uani d . 1 . . O C14 .05602(8) .00890(8) .20362(7) .0286(3) Uani d . 1 . . C C15 .09081(8) .01266(8) .13758(7) .0284(3) Uani d . 1 . . C C16 .17401(9) .01907(9) .12828(8) .0356(3) Uani d . 1 . . C H16 .1974 .0220 .0833 .043 Uiso calc R 1 . . H C17 .22271(9) .02111(10) .18766(9) .0429(4) Uani d . 1 . . C H17 .2805 .0261 .1830 .051 Uiso calc R 1 . . H C18 .18870(10) .01609(11) .25285(9) .0453(4) Uani d . 1 . . C H18 .2235 .0171 .2922 .054 Uiso calc R 1 . . H C19 .10389(10) .00956(10) .26210(8) .0381(3) Uani d . 1 . . C H19 .0804 .0057 .3070 .046 Uiso calc R 1 . . H C20 -.12094(10) .05719(10) .09834(9) .0400(4) Uani d . 1 . . C H20A -.1716 .0408 .1221 .060 Uiso calc R 1 . . H H20B -.1276 .0490 .0484 .060 Uiso calc R 1 . . H H20C -.1089 .1173 .1079 .060 Uiso calc R 1 . . H N2 -.07292(7) -.10077(7) .11295(6) .0273(2) Uani d . 1 . . N C21 -.09672(9) -.15167(10) .16502(7) .0352(3) Uani d . 1 . . C H21 -.0948 -.1308 .2111 .042 Uiso calc R 1 . . H C22 -.12390(10) -.23347(10) .15311(8) .0398(4) Uani d . 1 . . C H22 -.1396 -.2684 .1910 .048 Uiso calc R 1 . . H C23 -.12852(9) -.26529(9) .08646(7) .0325(3) Uani d . 1 . . C C24 -.10337(8) -.21178(9) .03314(7) .0309(3) Uani d . 1 . . C H24 -.1052 -.2311 -.0134 .037 Uiso calc R 1 . . H C25 -.07582(8) -.13073(9) .04782(7) .0302(3) Uani d . 1 . . C H25 -.0584 -.0950 .0109 .036 Uiso calc R 1 . . H C26 -.15942(12) -.35388(10) .07190(9) .0470(4) Uani d . 1 . . C H26A -.1129 -.3919 .0630 .071 Uiso calc R 1 . . H H26B -.1953 -.3527 .0312 .071 Uiso calc R 1 . . H H26C -.1903 -.3748 .1120 .071 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 B1 .0348(8) .0256(7) .0362(8) .0026(6) -.0045(6) .0031(6) O1 .0342(5) .0225(5) .0409(5) .0021(4) -.0103(4) .0003(4) O2 .0377(6) .0311(5) .0327(5) .0079(4) -.0024(4) -.0023(4) C1 .0342(7) .0249(6) .0278(6) -.0014(5) -.0024(5) .0032(5) C2 .0362(7) .0282(7) .0229(6) .0011(5) .0016(5) .0035(5) C3 .0539(9) .0279(7) .0245(6) -.0035(6) .0010(6) -.0003(5) C4 .0504(9) .0401(8) .0305(7) -.0164(7) -.0038(6) .0011(6) C5 .0343(8) .0509(9) .0392(8) -.0064(7) -.0053(6) .0043(7) C6 .0348(8) .0346(7) .0388(8) .0032(6) -.0032(6) .0008(6) C7 .0371(8) .0444(9) .0587(10) -.0021(7) -.0054(7) .0170(8) N1 .0277(6) .0217(5) .0351(6) -.0002(4) -.0055(5) -.0010(4) C8 .0379(7) .0244(6) .0398(8) .0047(6) -.0081(6) -.0017(6) C9 .0377(8) .0314(7) .0449(8) .0021(6) -.0069(6) .0081(6) C10 .0285(7) .0531(10) .0370(8) .0002(6) .0000(6) .0072(7) C11 .0354(8) .0489(9) .0386(8) .0041(7) .0030(6) -.0082(7) C12 .0297(7) .0268(7) .0434(8) .0027(5) -.0020(6) -.0049(6) C13 .0620(12) .0956(16) .0368(9) .0133(11) .0069(8) .0167(10) B2 .0333(8) .0281(7) .0290(7) -.0043(6) .0007(6) .0037(6) O3 .0301(5) .0350(5) .0284(5) -.0023(4) .0030(4) -.0005(4) O4 .0344(5) .0364(5) .0262(5) -.0082(4) .0000(4) .0052(4) C14 .0306(7) .0247(6) .0303(7) .0008(5) .0016(5) .0002(5) C15 .0339(7) .0222(6) .0292(6) -.0007(5) -.0008(5) -.0001(5) C16 .0349(7) .0324(7) .0395(8) -.0015(6) .0078(6) -.0041(6) C17 .0287(7) .0453(9) .0546(10) .0030(7) -.0008(7) -.0068(7) C18 .0402(8) .0533(10) .0425(9) .0054(7) -.0110(7) -.0035(7) C19 .0420(8) .0425(8) .0297(7) .0027(7) -.0021(6) -.0015(6) C20 .0390(8) .0312(8) .0498(9) -.0025(6) -.0071(7) .0053(7) N2 .0274(6) .0283(6) .0261(5) -.0008(4) .0017(4) .0052(4) C21 .0443(8) .0371(8) .0242(6) -.0071(6) .0019(6) .0046(6) C22 .0527(9) .0372(8) .0294(7) -.0122(7) .0023(6) .0094(6) C23 .0322(7) .0309(7) .0344(7) -.0037(6) .0012(6) .0041(6) C24 .0322(7) .0339(7) .0267(6) -.0009(6) .0031(5) .0001(6) C25 .0327(7) .0324(7) .0256(6) -.0010(6) .0050(5) .0056(5) C26 .0597(11) .0373(8) .0440(9) -.0165(8) .0005(8) .0028(7) 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 O1 . 1.4816(18) yes B1 O2 . 1.4716(19) yes B1 C7 . 1.587(2) yes B1 N1 . 1.660(2) yes O1 C1 . 1.3668(16) yes O2 C2 . 1.3637(17) yes C1 C6 . 1.373(2) no C1 C2 . 1.3955(19) no C2 C3 . 1.375(2) no C3 C4 . 1.394(2) no C4 C5 . 1.382(2) no C5 C6 . 1.400(2) no N1 C8 . 1.3416(17) no N1 C12 . 1.3450(18) no C8 C9 . 1.377(2) no C9 C10 . 1.383(2) no C10 C11 . 1.393(2) no C10 C13 . 1.500(2) no C11 C12 . 1.375(2) no B2 O3 . 1.4804(18) yes B2 O4 . 1.4865(18) yes B2 C20 . 1.588(2) yes B2 N2 . 1.6444(19) yes O3 C14 . 1.3655(16) yes O4 C15 . 1.3633(16) yes C14 C19 . 1.374(2) no C14 C15 . 1.3982(19) no C15 C16 . 1.3732(19) no C16 C17 . 1.396(2) no C17 C18 . 1.379(2) no C18 C19 . 1.399(2) no N2 C21 . 1.3415(17) no N2 C25 . 1.3444(17) no C21 C22 . 1.376(2) no C22 C23 . 1.383(2) no C23 C24 . 1.3904(19) no C23 C26 . 1.503(2) no C24 C25 . 1.377(2) no