#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011544.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_2011544 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first e526 _journal_page_last e527 _publ_section_title ; Methyl 2-methyl-6-methylthio-1,3-dioxo-4-[(2,3,4,6-tetra-O-acetyl-\b-D- glucopyranosyl)amino]-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carboxylate ; _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' loop_ _publ_author_name 'Low, John Nicolson' 'Garcia, Celeste' 'Melguizo, Manuel' 'Cobo, Justo' "S\'anchez, Adolfo" 'Nogueras, Manuel' "L\'opez, M. D." _chemical_formula_moiety 'C25 H29 N3 O13 S' _chemical_formula_sum 'C25 H29 N3 O13 S' _chemical_formula_weight 611.57 _chemical_melting_point '481' _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.1696(9) _cell_length_b 6.9695(7) _cell_length_c 21.526(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.036(5) _cell_angle_gamma 90.00 _cell_volume 1524.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150.0(10) _exptl_crystal_density_diffrn 1.332 _diffrn_ambient_temperature 150.0(10) 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 C1 -.2682(5) -.0651(9) -.5476(3) .0394(13) Uani d . 1 A . C O1 -.2645(3) -.0447(6) -.60250(17) .0481(10) Uani d . 1 . . O N2 -.3861(4) -.0885(7) -.51609(19) .0369(12) Uani d . 1 . . N C21 -.5134(5) -.1032(9) -.5491(2) .0469(16) Uani d . 1 . . C C3 -.3664(5) -.0869(8) -.4519(2) .0333(13) Uani d . 1 . . C O3 -.4534(3) -.1040(5) -.41460(16) .0412(10) Uani d . 1 . . O C4 -.0238(5) -.0494(9) -.4934(2) .0332(12) Uani d . 1 A . C O41 .1686(5) .0193(12) -.5509(3) .038(2) Uiso d P .711(16) A 1 O O41A .1701(10) -.102(3) -.5510(7) .053(6) Uiso d PD .289(16) A 2 O C41 .0553(5) -.0473(9) -.5508(3) .0393(14) Uani d D 1 . . C O42 -.0075(5) -.1201(12) -.5992(2) .035(2) Uiso d P .711(16) A 1 O O42A -.0145(11) -.023(3) -.6026(4) .047(6) Uiso d PD .289(16) A 2 O C42 .0556(6) -.0897(12) -.6573(2) .064(2) Uani d D 1 . . C C5 .0397(4) -.0551(9) -.4334(2) .0335(12) Uani d . 1 . . C S5 .21136(12) -.0540(2) -.42639(7) .0423(4) Uani d . 1 A . S C51 .2369(5) -.0838(11) -.3438(2) .0577(19) Uani d . 1 . . C N6 -.0256(4) -.0546(8) -.38019(18) .0371(11) Uani d . 1 A . N C7 -.1593(5) -.0600(8) -.3839(2) .0337(12) Uani d . 1 . . C N7 -.2245(4) -.0560(7) -.33035(17) .0336(10) Uani d . 1 A . N O7 -.1373(3) -.2294(5) -.24636(16) .0380(10) Uani d . 1 A . O C71 -.1671(5) -.0437(9) -.2691(2) .0383(13) Uani d . 1 . . C C72 -.2670(5) .0447(8) -.2263(2) .0350(14) Uani d . 1 A . C O721 -.2872(3) .2466(5) -.24187(16) .0387(10) Uani d . 1 . . O C721 -.3988(6) .2919(10) -.2760(3) .0436(16) Uani d . 1 A . C C722 -.4138(6) .4993(8) -.2834(3) .0551(18) Uani d . 1 . . C O722 -.4772(4) .1695(6) -.29357(18) .0502(11) Uani d . 1 . . O C73 -.2194(5) .0394(9) -.1574(3) .0363(14) Uani d . 1 . . C O731 -.3296(3) .1033(6) -.12282(17) .0461(11) Uani d . 1 A . O C731 -.3070(7) .2424(11) -.0796(3) .0594(19) Uani d . 1 . . C C732 -.4329(7) .2874(12) -.0476(4) .103(3) Uani d . 1 A . C O732 -.2014(5) .3132(8) -.0695(2) .095(2) Uani d . 1 A . O C74 -.1814(5) -.1620(9) -.1400(2) .0382(15) Uani d . 1 A . C O741 -.1241(4) -.1642(6) -.07900(17) .0493(11) Uani d . 1 . . O C741 -.2026(7) -.2204(10) -.0323(3) .0547(18) Uani d . 1 A . C C742 -.1241(8) -.2292(16) .0287(3) .116(4) Uani d . 1 . . C O742 -.3159(5) -.2534(8) -.0389(2) .0727(15) Uani d . 1 . . O C75 -.0781(5) -.2312(8) -.1848(2) .0397(15) Uani d . 1 . . C C751 -.0349(5) -.4340(9) -.1719(3) .0385(15) Uani d . 1 A . C O751 .0924(3) -.4557(7) -.1991(2) .0508(12) Uani d . 1 . . O C752 .1375(6) -.6339(11) -.2043(3) .0472(17) Uani d . 1 A . C C753 .2694(6) -.6396(11) -.2336(3) .075(2) Uani d . 1 . . C O752 .0779(4) -.7718(7) -.1892(2) .0557(12) Uani d . 1 . . O C8 -.1626(5) -.0593(8) -.4953(2) .0314(12) Uani d . 1 . . C C9 -.2256(4) -.0661(8) -.4401(2) .0286(12) Uani d . 1 A . C H21A -.5783 -.1561 -.5212 .070 Uiso calc PR .50 . . H H21B -.5057 -.1879 -.5851 .070 Uiso calc PR .50 . . H H21C -.5418 .0244 -.5632 .070 Uiso calc PR .50 . . H H21D -.5056 -.0569 -.5918 .070 Uiso calc PR .50 . . H H21E -.5782 -.0252 -.5279 .070 Uiso calc PR .50 . . H H21F -.5421 -.2375 -.5498 .070 Uiso calc PR .50 . . H H42A -.0087 -.1080 -.6918 .096 Uiso calc PR .50 A 1 H H42B .1277 -.1818 -.6611 .096 Uiso calc PR .50 A 1 H H42C .0906 .0411 -.6585 .096 Uiso calc PR .50 A 1 H H42D .1484 -.0578 -.6491 .096 Uiso calc PR .50 A 1 H H42E .0120 .0161 -.6799 .096 Uiso calc PR .50 A 1 H H42F .0492 -.2069 -.6824 .096 Uiso calc PR .50 A 1 H H51A .3297 -.1136 -.3343 .087 Uiso calc PR .50 A . H H51B .1818 -.1890 -.3294 .087 Uiso calc PR .50 . . H H51C .2133 .0351 -.3226 .087 Uiso calc PR .50 . . H H51D .1535 -.0648 -.3232 .087 Uiso calc PR .50 . . H H51E .3014 .0107 -.3281 .087 Uiso calc PR .50 . . H H51F .2699 -.2134 -.3350 .087 Uiso calc PR .50 . . H H7 -.3110 -.0615 -.3336 .040 Uiso calc R 1 . . H H71 -.0856 .0365 -.2692 .046 Uiso calc R 1 A . H H72 -.3525 -.0255 -.2312 .042 Uiso calc R 1 . . H H23A -.3471 .5651 -.2573 .083 Uiso calc PR .50 A . H H23B -.5017 .5377 -.2709 .083 Uiso calc PR .50 . . H H23C -.4026 .5340 -.3270 .083 Uiso calc PR .50 . . H H23D -.4872 .5262 -.3129 .083 Uiso calc PR .50 . . H H23E -.3326 .5535 -.2992 .083 Uiso calc PR .50 . . H H23F -.4316 .5572 -.2431 .083 Uiso calc PR .50 . . H H73 -.1429 .1279 -.1503 .044 Uiso calc R 1 A . H H32A -.4872 .1715 -.0459 .155 Uiso calc PR .50 . . H H32B -.4812 .3876 -.0708 .155 Uiso calc PR .50 . . H H32C -.4121 .3325 -.0052 .155 Uiso calc PR .50 . . H H32D -.4332 .4229 -.0354 .155 Uiso calc PR .50 . . H H32E -.4391 .2068 -.0105 .155 Uiso calc PR .50 . . H H32F -.5082 .2619 -.0760 .155 Uiso calc PR .50 . . H H74 -.2603 -.2476 -.1425 .046 Uiso calc R 1 . . H H742A -.0343 -.2722 .0212 .174 Uiso calc PR .50 A . H H742B -.1659 -.3196 .0568 .174 Uiso calc PR .50 . . H H742C -.1213 -.1015 .0478 .174 Uiso calc PR .50 . . H H742D -.1800 -.1900 .0627 .174 Uiso calc PR .50 . . H H742E -.0484 -.1426 .0271 .174 Uiso calc PR .50 . . H H742F -.0931 -.3607 .0360 .174 Uiso calc PR .50 . . H H75 -.0002 -.1435 -.1828 .048 Uiso calc R 1 A . H H751A -.0280 -.4577 -.1266 .046 Uiso calc R 1 . . H H751B -.0988 -.5260 -.1908 .046 Uiso calc R 1 . . H H753A .3088 -.5113 -.2322 .113 Uiso calc PR .50 A . H H753B .2583 -.6813 -.2769 .113 Uiso calc PR .50 . . H H753C .3270 -.7299 -.2108 .113 Uiso calc PR .50 . . H H753D .2873 -.7703 -.2477 .113 Uiso calc PR .50 . . H H753E .3378 -.6003 -.2030 .113 Uiso calc PR .50 . . H H753F .2691 -.5517 -.2691 .113 Uiso calc PR .50 . . 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 C1 .039(3) .044(4) .036(3) .007(3) .008(3) .003(4) O1 .057(2) .061(3) .027(2) .002(2) .0045(18) .001(2) N2 .027(2) .050(3) .034(3) -.006(2) .001(2) -.002(2) C21 .045(4) .060(5) .036(3) .004(3) .002(3) -.001(3) C3 .034(3) .029(4) .038(3) -.001(3) .012(3) -.007(3) O3 .034(2) .053(3) .037(2) .0008(19) .0080(17) -.002(2) C4 .028(3) .035(3) .037(3) -.009(3) .011(2) -.014(3) C41 .026(3) .030(3) .063(4) -.008(3) .014(3) -.007(4) C42 .064(4) .105(6) .025(3) -.007(4) .023(3) -.002(4) C5 .035(3) .031(3) .034(3) -.010(3) .004(2) .008(3) S5 .0282(7) .0548(10) .0442(9) -.0012(8) .0065(6) -.0047(9) C51 .044(4) .085(6) .044(4) -.004(4) -.006(3) -.013(4) N6 .036(3) .048(3) .028(2) -.001(2) .0076(19) .000(3) C7 .036(3) .026(3) .039(3) .002(3) .008(3) .005(3) N7 .032(2) .041(3) .029(2) .006(2) .0089(19) .003(3) O7 .040(2) .046(3) .028(2) -.0024(19) .0032(17) -.0031(19) C71 .034(3) .048(4) .033(3) .005(3) .004(2) .006(3) C72 .030(3) .036(3) .040(4) -.005(3) .013(3) -.004(3) O721 .032(2) .042(3) .041(2) -.0008(18) .0054(18) -.006(2) C721 .025(3) .059(5) .047(4) .012(3) .003(3) -.007(3) C722 .051(4) .051(5) .064(5) .003(3) .007(3) .008(3) O722 .039(2) .058(3) .053(3) .002(2) .001(2) -.008(2) C73 .027(3) .045(4) .037(4) -.002(3) .004(3) -.009(3) O731 .036(2) .063(3) .041(2) -.0032(19) .0154(19) -.013(2) C731 .071(5) .057(5) .052(5) -.010(4) .031(4) -.018(4) C732 .069(5) .103(7) .143(8) -.023(5) .082(5) -.052(6) O732 .067(4) .119(5) .100(4) -.039(3) .028(3) -.061(4) C74 .038(3) .051(4) .025(3) -.005(3) .008(3) .000(3) O741 .044(2) .076(3) .028(2) -.002(2) .0007(19) .003(2) C741 .065(5) .073(5) .027(4) .007(4) .011(3) .000(3) C742 .124(7) .195(12) .028(4) .006(7) -.011(4) .044(6) O742 .059(3) .109(4) .052(3) -.007(3) .024(3) .015(3) C75 .037(3) .055(4) .028(3) .003(3) .015(3) .002(3) C751 .033(3) .050(4) .033(3) .004(3) .014(3) .001(3) O751 .030(2) .061(3) .062(3) .005(2) .011(2) .001(2) C752 .033(3) .050(4) .059(4) -.005(4) .006(3) -.016(4) C753 .049(4) .090(6) .087(5) .005(4) .017(4) -.024(5) O752 .042(3) .052(3) .073(3) -.003(2) .011(2) -.008(3) C8 .038(3) .026(3) .032(3) .006(3) .012(2) -.012(3) C9 .026(3) .026(3) .034(3) -.006(3) .004(2) -.006(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 C1 O1 . 1.192(5) no C1 N2 . 1.408(6) no C1 C8 . 1.529(7) no N2 C3 . 1.388(6) no N2 C21 . 1.459(6) no C21 H21A . .9800 no C21 H21B . .9800 no C21 H21C . .9800 no C21 H21D . .9800 no C21 H21E . .9800 no C21 H21F . .9800 no C3 O3 . 1.222(5) no C3 C9 . 1.453(7) no C4 C8 . 1.413(6) no C4 C5 . 1.425(7) no C4 C41 . 1.497(7) no O41 C41 . 1.242(7) no O41A C41 . 1.229(9) no C41 O42 . 1.305(8) no C41 O42A . 1.311(9) no O42 C42 . 1.442(7) no O42A C42 . 1.473(9) no C42 H42A . .9800 no C42 H42B . .9800 no C42 H42D . .9800 no C42 H42E . .9800 no C42 H42F . .9800 no C5 N6 . 1.343(6) no C5 S5 . 1.747(5) no S5 C51 . 1.800(6) no C51 H51A . .9800 no C51 H51B . .9800 no C51 H51C . .9800 no C51 H51D . .9800 no C51 H51E . .9800 no C51 H51F . .9800 no N6 C7 . 1.361(6) no C7 N7 . 1.350(6) no C7 C9 . 1.364(6) no N7 C71 . 1.425(6) no N7 H7 . .8800 no O7 C71 . 1.413(7) no O7 C75 . 1.436(6) no C71 C72 . 1.526(7) no C71 H71 . 1.0000 no C72 O721 . 1.459(7) no C72 C73 . 1.544(7) no C72 H72 . 1.0000 no O721 C721 . 1.367(7) no C721 O722 . 1.219(7) no C721 C722 . 1.461(9) no C722 H23A . .9800 no C722 H23B . .9800 no C722 H23C . .9800 no C722 H23D . .9800 no C722 H23E . .9800 no C722 H23F . .9800 no C73 O731 . 1.437(6) no C73 C74 . 1.500(8) no C73 H73 . 1.0000 no O731 C731 . 1.358(7) no C731 O732 . 1.194(7) no C731 C732 . 1.509(8) no C732 H32A . .9800 no C732 H32B . .9800 no C732 H32C . .9800 no C732 H32D . .9800 no C732 H32E . .9800 no C732 H32F . .9800 no C74 O741 . 1.418(6) no C74 C75 . 1.529(7) no C74 H74 . 1.0000 no O741 C741 . 1.363(7) no C741 O742 . 1.178(7) no C741 C742 . 1.515(9) no C742 H742A . .9800 no C742 H742B . .9800 no C742 H742C . .9800 no C742 H742D . .9800 no C742 H742E . .9800 no C742 H742F . .9800 no C75 C751 . 1.504(8) no C75 H75 . 1.0000 no C751 O751 . 1.448(6) no C751 H751A . .9900 no C751 H751B . .9900 no O751 C752 . 1.330(7) no C752 O752 . 1.188(7) no C752 C753 . 1.502(8) no C753 H753A . .9800 no C753 H753B . .9800 no C753 H753C . .9800 no C753 H753D . .9800 no C753 H753E . .9800 no C753 H753F . .9800 no C8 C9 . 1.370(6) no