#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006949.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_2006949 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1998 _journal_volume 54 _journal_page_first 77 _journal_page_last 79 _publ_section_title ; The First Determination of the Absolute Configuration of an Atropisomeric Flavin Derivative ; _space_group_IT_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _[local]_cod_cif_authors_sg_H-M 'P 21' _[local]_cod_cif_authors_sg_Hall 'P 2y1' loop_ _publ_author_name ' Yasushi Kawai ' ' Jun Kunitomo ' ' Atsuyoshi Ohno ' _chemical_formula_moiety 'C28 H23 Br2 N3 O2, C H4 O' _chemical_formula_sum 'C29 H27 Br2 N3 O3' _chemical_formula_analytical 'C55.52 H4.30 N6.65' _chemical_formula_weight 625.36 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' _cell_length_a 20.913(7) _cell_length_b 10.868(8) _cell_length_c 12.030(10) _cell_angle_alpha 90 _cell_angle_beta 100.45(4) _cell_angle_gamma 90 _cell_volume 2687(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173.2 _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_meas 1.51 _diffrn_ambient_temperature 173.2 _refine_ls_R_factor_obs .034 _refine_ls_wR_factor_obs .052 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_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy Br1A .40516(3) .0340 -.47060(4) .02580(10) Uani d . S 1.00 Br1B .04273(3) .33136(8) .07680(5) .0364(2) Uani d . . 1.00 Br2A .64987(2) .25713(7) -.34657(4) .02760(10) Uani d . . 1.00 Br2B -.14543(3) .39421(7) .35228(5) .02990(10) Uani d . . 1.00 O1A .4172(2) .0309(4) -.1093(3) .0271(9) Uani d . . 1.00 O1B .0875(2) .6300(4) .1174(3) .0255(10) Uani d . . 1.00 O2A .3358(2) .2881(3) -.3985(3) .0264(10) Uani d . . 1.00 O2B .1693(2) .3702(4) .4052(3) .0270(10) Uani d . . 1.00 O3A .3478(2) -.0183(4) .1098(3) .0380(10) Uani d . . 1.00 O3B .1494(2) .6724(4) -.1110(3) .0400(10) Uani d . . 1.00 N1A .3107(2) .0852(4) -.1217(3) .0210(10) Uani d . . 1.00 N1B .1916(2) .5682(4) .1258(3) .0190(10) Uani d . . 1.00 N2A .3779(2) .1637(4) -.2508(3) .0180(10) Uani d . . 1.00 N2B .1264(2) .4939(4) .2576(3) .0220(10) Uani d . . 1.00 N3A .2022(2) .1405(4) -.1469(3) .0190(10) Uani d . . 1.00 N3B .2992(2) .5061(4) .1461(3) .0170(10) Uani d . . 1.00 C1A .3697(3) .0873(5) -.1570(4) .0200(10) Uani d . . 1.00 C1B .1344(3) .5694(4) .1632(4) .0180(10) Uani d . . 1.00 C2A .3273(3) .2215(5) -.3210(4) .0220(10) Uani d . . 1.00 C2B .1765(2) .4320(5) .3240(4) .0190(10) Uani d . . 1.00 C3A .2626(2) .2030(4) -.2883(4) .0160(10) Uani d . . 1.00 C3B .2401(2) .4474(5) .2903(4) .0180(10) Uani d . . 1.00 C4A .2079(3) .2519(5) -.3527(4) .0220(10) Uani d . . 1.00 C4B .2943(2) .3962(5) .3525(4) .0200(10) Uani d . . 1.00 C5A .1476(2) .2486(5) -.3145(4) .0210(10) Uani d . . 1.00 C5B .3542(2) .3987(5) .3123(4) .0180(10) Uani d . . 1.00 C6A .0917(2) .3032(5) -.3756(4) .0240(10) Uani d . . 1.00 C6B .4105(3) .3430(5) .3733(4) .0240(10) Uani d . . 1.00 C7A .0355(3) .3054(5) -.3322(5) .0260(10) Uani d . . 1.00 C7B .4660(3) .3386(6) .3292(5) .0270(10) Uani d . . 1.00 C8A .0332(2) .2498(5) -.2280(4) .0220(10) Uani d . . 1.00 C8B .4678(3) .3942(5) .2232(5) .0280(10) Uani d . . 1.00 C9A .0871(2) .1944(5) -.1666(4) .0200(10) Uani d . . 1.00 C9B .4136(3) .4499(5) .1623(4) .0240(10) Uani d . . 1.00 C10A .1464(2) .1937(4) -.2085(4) .0160(10) Uani d . . 1.00 C10B .3568(3) .4526(5) .2065(4) .0210(10) Uani d . . 1.00 C11A .2609(2) .1405(4) -.1843(4) .0160(10) Uani d . . 1.00 C11B .2421(2) .5099(4) .1866(4) .0190(10) Uani d . . 1.00 C12A .4429(2) .1836(5) -.2722(4) .0180(10) Uani d . . 1.00 C12B .0622(2) .4739(4) .2806(4) .0190(10) Uani d . . 1.00 C13A .4615(2) .1343(5) -.3673(4) .0190(10) Uani d . . 1.00 C13B .0179(2) .4008(5) .2069(4) .0200(10) Uani d . . 1.00 C14A .5236(3) .1559(5) -.3927(4) .0210(10) Uani d . . 1.00 C14B -.0439(2) .3760(5) .2268(4) .0230(10) Uani d . . 1.00 C15A .5655(2) .2278(5) -.3177(4) .0220(10) Uani d . . 1.00 C15B -.0601(3) .4250(5) .3232(4) .0220(10) Uani d . . 1.00 C16A .5470(3) .2784(5) -.2220(4) .0240(10) Uani d . . 1.00 C16B -.0184(3) .4964(4) .3974(4) .0180(10) Uani d . . 1.00 C17A .4849(2) .2578(5) -.1989(4) .0230(10) Uani d . . 1.00 C17B .0439(2) .5218(5) .3783(4) .0190(10) Uani d . . 1.00 C18A .4670(3) .3142(6) -.0949(5) .035(2) Uani d . . 1.00 C18B .0889(3) .6004(5) .4590(4) .0270(10) Uani d . . 1.00 C19A .1998(3) .0957(5) -.0341(4) .0190(10) Uani d . . 1.00 C19B .3010(2) .5522(5) .0327(4) .0180(10) Uani d . . 1.00 C20A .1892(2) -.0271(5) -.0141(4) .0210(10) Uani d . . 1.00 C20B .3102(3) .6756(5) .0140(4) .0220(10) Uani d . . 1.00 C21A .1809(3) -.0628(5) .0933(4) .0210(10) Uani d . . 1.00 C21B .3160(2) .7131(5) -.0939(4) .0220(10) Uani d . . 1.00 C22A .1847(2) .0225(5) .1816(4) .0180(10) Uani d . . 1.00 C22B .3127(2) .6318(5) -.1822(4) .0200(10) Uani d . . 1.00 C23A .1966(3) .1440(5) .1586(4) .0230(10) Uani d . . 1.00 C23B .3023(3) .5076(5) -.1609(4) .0240(10) Uani d . . 1.00 C24A .2042(3) .1821(5) .0516(4) .0230(10) Uani d . . 1.00 C24B .2967(3) .4677(5) -.0541(5) .0240(10) Uani d . . 1.00 C25A .1748(3) -.0121(5) .3009(4) .0240(10) Uani d . . 1.00 C25B .3210(3) .6683(5) -.3024(4) .0260(10) Uani d . . 1.00 C26A .2332(3) .0334(6) .3883(4) .035(2) Uani d . . 1.00 C26B .2630(3) .6213(6) -.3892(5) .034(2) Uani d . . 1.00 C27A .1688(3) -.1516(6) .3154(5) .034(2) Uani d . . 1.00 C27B .3249(3) .8086(5) -.3154(4) .030(2) Uani d . . 1.00 C28A .1117(3) .0490(7) .3224(5) .039(2) Uani d . . 1.00 C28B .3846(3) .6110(6) -.3267(5) .037(2) Uani d . . 1.00 C29A .3798(4) .0804(7) .1668(6) .055(2) Uani d . . 1.00 C29B .1151(4) .5739(7) -.1624(6) .058(2) Uani d . . 1.00 H1A .2104 .2896 -.4238 .0269 Uiso calc . . 1.00 H1B .2924 .3589 .4236 .0222 Uiso calc . . 1.00 H2A .0921 .3389 -.4474 .0269 Uiso calc . . 1.00 H2B .4100 .3082 .4457 .0298 Uiso calc . . 1.00 H3A -.0018 .3446 -.3730 .0311 Uiso calc . . 1.00 H3B .5029 .2973 .3698 .0315 Uiso calc . . 1.00 H4A -.0062 .2514 -.1992 .0269 Uiso calc . . 1.00 H4B .5074 .3939 .1945 .0329 Uiso calc . . 1.00 H5A .0849 .1556 -.0969 .0226 Uiso calc . . 1.00 H5B .4152 .4858 .0905 .0293 Uiso calc . . 1.00 H6A .5367 .1225 -.4587 .0253 Uiso calc . . 1.00 H6B -.0737 .3271 .1759 .0279 Uiso calc . . 1.00 H7A .5775 .3268 -.1721 .0286 Uiso calc . . 1.00 H7B -.0322 .5284 .4626 .0218 Uiso calc . . 1.00 H8A .4950 .2833 -.0292 .0424 Uiso calc . . 1.00 H8B .0969 .5611 .5314 .0315 Uiso calc . . 1.00 H9A .4701 .4004 -.0972 .0424 Uiso calc . . 1.00 H9B .1289 .6091 .4331 .0315 Uiso calc . . 1.00 H10A .4231 .2914 -.0902 .0424 Uiso calc . . 1.00 H10B .0701 .6784 .4654 .0315 Uiso calc . . 1.00 H11A .1873 -.0857 -.0728 .0245 Uiso calc . . 1.00 H11B .3133 .7341 .0743 .0250 Uiso calc . . 1.00 H12A .1727 -.1467 .1073 .0248 Uiso calc . . 1.00 H12B .3224 .7974 -.1075 .0251 Uiso calc . . 1.00 H13A .2003 .2032 .2177 .0255 Uiso calc . . 1.00 H13B .2992 .4495 -.2206 .0284 Uiso calc . . 1.00 H14A .2123 .2662 .0372 .0267 Uiso calc . . 1.00 H14B .2901 .3834 -.0405 .0280 Uiso calc . . 1.00 H15A .2267 .0137 .4624 .0417 Uiso calc . . 1.00 H15B .2239 .6588 -.3757 .0391 Uiso calc . . 1.00 H16A .2719 -.0066 .3750 .0417 Uiso calc . . 1.00 H16B .2690 .6422 -.4638 .0391 Uiso calc . . 1.00 H17A .2378 .1194 .3813 .0417 Uiso calc . . 1.00 H17B .2595 .5347 -.3834 .0391 Uiso calc . . 1.00 H18A .1627 -.1701 .3896 .0393 Uiso calc . . 1.00 H18B .3600 .8407 -.2631 .0343 Uiso calc . . 1.00 H19A .1326 -.1815 .2623 .0393 Uiso calc . . 1.00 H19B .3302 .8284 -.3905 .0343 Uiso calc . . 1.00 H20A .2073 -.1911 .3015 .0393 Uiso calc . . 1.00 H20B .2852 .8452 -.3023 .0343 Uiso calc . . 1.00 H21A .1152 .1358 .3163 .0450 Uiso calc . . 1.00 H21B .3837 .5245 -.3198 .0455 Uiso calc . . 1.00 H22A .0760 .0205 .2682 .0450 Uiso calc . . 1.00 H22B .3912 .6331 -.4002 .0455 Uiso calc . . 1.00 H23A .1047 .0287 .3963 .0450 Uiso calc . . 1.00 H23B .4210 .6422 -.2726 .0455 Uiso calc . . 1.00 H24A .3259 .0232 .0453 .0488 Uiso calc . . 1.00 H24B .1482 .6367 -.0357 .0488 Uiso calc . . 1.00 H25A .4050 .0520 .2378 .0680 Uiso calc . . 1.00 H25B .0738 .5680 -.1393 .0676 Uiso calc . . 1.00 H26A .4081 .1180 .1245 .0680 Uiso calc . . 1.00 H26B .1083 .5826 -.2424 .0676 Uiso calc . . 1.00 H27A .3492 .1393 .1841 .0680 Uiso calc . . 1.00 H27B .1384 .4990 -.1419 .0676 Uiso calc . . 1.00 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 Br1A .0222(3) .0304(3) .0240(3) -.0086(2) .0022(2) -.0037(2) Br1B .0321(3) .0469(4) .0326(3) -.0013(3) .0125(2) -.0174(3) Br2A .0154(3) .0364(3) .0322(3) -.0048(2) .0074(2) .0032(2) Br2B .0184(3) .0400(3) .0335(3) -.0051(2) .0105(2) .0030(2) O1A .022(2) .031(2) .029(2) .011(2) .006(2) .013(2) O1B .016(2) .037(2) .023(2) .004(2) .0030(10) .008(2) O2A .019(2) .035(2) .027(2) .001(2) .009(2) .015(2) O2B .018(2) .040(2) .024(2) .002(2) .0090(10) .013(2) O3A .039(3) .040(2) .032(2) .000(2) -.003(2) .008(2) O3B .043(3) .039(2) .035(2) -.002(2) -.002(2) .011(2) N1A .021(2) .022(2) .020(2) .002(2) .008(2) .004(2) N1B .011(2) .027(2) .019(2) .004(2) .001(2) .004(2) N2A .011(2) .025(2) .017(2) -.004(2) .004(2) .005(2) N2B .019(2) .026(2) .022(2) -.001(2) .008(2) .001(2) N3A .017(2) .022(2) .018(2) .001(2) .006(2) .001(2) N3B .010(2) .024(2) .018(2) -.001(2) .002(2) .003(2) C1A .025(3) .021(2) .014(2) -.001(2) .005(2) .001(2) C1B .020(3) .021(3) .014(2) -.001(2) .006(2) -.001(2) C2A .023(3) .021(3) .023(3) .001(2) .009(2) -.002(2) C2B .012(2) .024(3) .022(3) -.003(2) .003(2) -.002(2) C3A .012(2) .016(2) .021(2) .001(2) .006(2) .001(2) C3B .014(3) .024(3) .016(2) -.001(2) .003(2) .001(2) C4A .024(3) .025(3) .018(2) -.002(2) .005(2) .003(2) C4B .014(2) .021(2) .023(2) -.002(2) .004(2) .001(2) C5A .023(3) .019(2) .025(3) -.002(2) .011(2) -.002(2) C5B .018(2) .020(2) .016(2) .000(2) .001(2) .004(2) C6A .021(3) .026(3) .024(3) -.002(2) .005(2) .010(2) C6B .025(3) .021(3) .027(3) .000(2) .008(2) .003(2) C7A .016(3) .027(3) .035(3) -.001(2) .002(2) .002(2) C7B .019(3) .029(3) .034(3) .009(2) .004(2) .007(2) C8A .020(3) .024(3) .024(3) .000(2) .008(2) -.003(2) C8B .023(3) .028(3) .037(3) -.001(2) .013(2) -.002(3) C9A .013(3) .024(3) .024(3) -.006(2) .009(2) -.002(2) C9B .029(3) .024(3) .021(3) .003(2) .012(2) .004(2) C10A .015(2) .015(2) .018(2) .004(2) .003(2) .001(2) C10B .020(3) .017(3) .027(3) -.003(2) .003(2) -.002(2) C11A .017(3) .016(2) .014(2) -.002(2) .001(2) .001(2) C11B .019(3) .018(3) .019(2) -.005(2) .004(2) -.001(2) C12A .008(2) .026(3) .020(2) .003(2) .003(2) .003(2) C12B .010(2) .023(3) .022(3) .002(2) .001(2) .005(2) C13A .013(2) .024(3) .017(2) -.005(2) -.002(2) .001(2) C13B .017(2) .028(3) .018(2) .004(2) .007(2) -.005(2) C14A .014(2) .029(3) .022(3) .002(2) .003(2) .004(2) C14B .015(2) .025(3) .028(3) -.005(2) -.001(2) .001(2) C15A .013(2) .026(3) .027(3) .002(2) .004(2) .009(2) C15B .019(3) .026(3) .022(3) .004(2) .008(2) .008(2) C16A .018(3) .030(3) .024(3) .003(2) .002(2) -.004(2) C16B .019(3) .020(3) .019(2) .000(2) .011(2) -.001(2) C17A .010(2) .028(3) .028(3) .000(2) -.001(2) .003(2) C17B .023(3) .016(2) .019(2) .002(2) .005(2) .004(2) C18A .033(3) .042(3) .033(3) -.004(3) .012(2) -.012(3) C18B .025(3) .034(3) .022(3) -.001(2) .004(2) -.004(2) C19A .019(3) .024(3) .016(2) -.003(2) .007(2) .003(2) C19B .008(2) .025(3) .021(2) .002(2) .002(2) .004(2) C20A .017(3) .024(3) .020(3) -.002(2) .002(2) -.002(2) C20B .025(3) .018(3) .023(3) .000(2) .007(2) -.001(2) C21A .020(3) .019(2) .025(3) -.005(2) .005(2) .002(2) C21B .019(3) .020(3) .027(3) -.004(2) .005(2) .002(2) C22A .012(2) .028(3) .015(2) .000(2) .003(2) .003(2) C22B .014(2) .026(3) .019(2) -.005(2) .004(2) .002(2) C23A .023(3) .026(3) .020(3) -.009(2) .006(2) -.005(2) C23B .029(3) .024(3) .020(3) -.001(2) .011(2) -.003(2) C24A .023(3) .020(3) .027(3) -.003(2) .009(2) .003(2) C24B .028(3) .018(3) .026(3) -.005(2) .007(2) -.002(2) C25A .020(3) .029(3) .022(3) -.002(2) .005(2) .004(2) C25B .034(3) .028(3) .018(2) -.004(2) .009(2) .004(2) C26A .050(4) .034(3) .019(2) -.008(3) .000(2) .002(3) C26B .034(3) .039(3) .026(3) -.008(3) -.001(2) .005(3) C27A .044(4) .034(3) .023(3) -.012(3) .003(2) .008(2) C27B .039(3) .031(3) .021(3) -.010(3) .009(2) .006(2) C28A .029(3) .063(4) .029(3) .010(3) .019(2) .011(3) C28B .035(4) .045(4) .037(3) .003(3) .020(3) .010(3) C29A .069(6) .042(4) .050(4) .005(4) -.001(4) -.005(3) C29B .074(6) .046(4) .045(4) .005(4) -.017(4) -.007(3) 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 Br1A C13A 1_555 1_555 1.895(5) no Br1B C13B 1_555 1_555 1.893(5) no Br2A C15A 1_555 1_555 1.886(5) no Br2B C15B 1_555 1_555 1.909(5) no O1A C1A 1_555 1_555 1.219(6) no O1B C1B 1_555 1_555 1.226(6) no O2A C2A 1_555 1_555 1.218(6) no O2B C2B 1_555 1_555 1.216(6) no O3A C29A 1_555 1_555 1.379(8) no O3B C29B 1_555 1_555 1.373(9) no N1A C1A 1_555 1_555 1.378(7) yes N1A C11A 1_555 1_555 1.314(6) yes N1B C1B 1_555 1_555 1.352(7) no N1B C11B 1_555 1_555 1.332(6) no N2A C1A 1_555 1_555 1.435(6) yes N2A C2A 1_555 1_555 1.379(6) yes N2A C12A 1_555 1_555 1.445(6) yes N2B C1B 1_555 1_555 1.435(6) no N2B C2B 1_555 1_555 1.373(7) no N2B C12B 1_555 1_555 1.436(6) no N3A C10A 1_555 1_555 1.389(6) yes N3A C11A 1_555 1_555 1.382(6) yes N3A C19A 1_555 1_555 1.451(6) yes N3B C10B 1_555 1_555 1.414(6) no N3B C11B 1_555 1_555 1.370(6) no N3B C19B 1_555 1_555 1.459(6) no C2A C3A 1_555 1_555 1.489(7) yes C2B C3B 1_555 1_555 1.467(7) no C3A C4A 1_555 1_555 1.368(7) yes C3A C11A 1_555 1_555 1.429(6) yes C3B C4B 1_555 1_555 1.360(7) no C3B C11B 1_555 1_555 1.428(7) no C4A C5A 1_555 1_555 1.418(7) yes C4B C5B 1_555 1_555 1.421(7) no C5A C6A 1_555 1_555 1.396(7) no C5A C10A 1_555 1_555 1.413(7) no C5B C6B 1_555 1_555 1.407(7) no C5B C10B 1_555 1_555 1.411(7) no C6A C7A 1_555 1_555 1.368(7) no C6B C7B 1_555 1_555 1.362(7) no C7A C8A 1_555 1_555 1.400(7) no C7B C8B 1_555 1_555 1.417(8) no C8A C9A 1_555 1_555 1.370(7) no C8B C9B 1_555 1_555 1.373(8) no C9A C10A 1_555 1_555 1.422(7) no C9B C10B 1_555 1_555 1.387(8) no C12A C13A 1_555 1_555 1.381(7) no C12A C17A 1_555 1_555 1.386(7) no C12B C13B 1_555 1_555 1.406(7) no C12B C17B 1_555 1_555 1.399(7) no C13A C14A 1_555 1_555 1.405(7) no C13B C14B 1_555 1_555 1.383(7) no C14A C15A 1_555 1_555 1.381(8) no C14B C15B 1_555 1_555 1.373(7) no C15A C16A 1_555 1_555 1.392(7) no C15B C16B 1_555 1_555 1.370(7) no C16A C17A 1_555 1_555 1.395(7) no C16B C17B 1_555 1_555 1.391(7) no C17A C18A 1_555 1_555 1.500(8) no C17B C18B 1_555 1_555 1.493(7) no C19A C20A 1_555 1_555 1.381(7) no C19A C24A 1_555 1_555 1.385(7) no C19B C20B 1_555 1_555 1.380(7) no C19B C24B 1_555 1_555 1.381(7) no C20A C21A 1_555 1_555 1.389(7) no C20B C21B 1_555 1_555 1.386(7) no C21A C22A 1_555 1_555 1.401(7) no C21B C22B 1_555 1_555 1.373(7) no C22A C23A 1_555 1_555 1.381(8) no C22A C25A 1_555 1_555 1.533(7) no C22B C23B 1_555 1_555 1.398(7) no C22B C25B 1_555 1_555 1.538(7) no C23A C24A 1_555 1_555 1.387(7) no C23B C24B 1_555 1_555 1.380(7) no C25A C26A 1_555 1_555 1.541(8) no C25A C27A 1_555 1_555 1.534(8) no C25A C28A 1_555 1_555 1.541(8) no C25B C26B 1_555 1_555 1.536(8) no C25B C27B 1_555 1_555 1.536(8) no C25B C28B 1_555 1_555 1.545(8) no