#------------------------------------------------------------------------------ #$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7150000.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_7150000 _journal_name_full 'Organic & Biomolecular Chemistry' _journal_year 2005 _publ_section_title ; Studies related to carba-pyranoses: synthesis of acetylated derivatives of 4-amino-2,4-dideoxy-3-O-(beta-D-glucopyranosyl)-beta-L-(and beta-D-) altrocarba-pyranose from a D-glucose template ; _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 'Wai Hung Yuen.' 'Robin G. Pritchard' 'R. Stoodley' _chemical_formula_moiety 'C22 H31 N1 O15' _chemical_formula_sum 'C22 H31 N O15' _chemical_formula_weight 549.48 _chemical_absolute_configuration rm _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.773(1) _cell_length_b 22.641(3) _cell_length_c 10.86(2) _cell_angle_alpha 90 _cell_angle_beta 105.380(2) _cell_angle_gamma 90 _cell_volume 1368.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_wavelength 0.71073 _exptl_crystal_density_diffrn 1.333 _diffrn_ambient_temperature 293(2) loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1' C 0.3903(15) 0.2891(4) 0.2544(8) 0.051(2) Uani 1 1 d . . . H1' H 0.2662 0.3037 0.2933 0.061 Uiso 1 1 calc R . . C1 C 0.2853(15) 0.1071(3) 0.4603(7) 0.049(2) Uani 1 1 d . . . H1 H 0.1222 0.1083 0.4035 0.058 Uiso 1 1 calc R . . C2' C 0.5719(15) 0.3368(3) 0.2559(7) 0.047(2) Uani 1 1 d . . . H2' H 0.7108 0.3201 0.2322 0.056 Uiso 1 1 calc R . . C2 C 0.4449(15) 0.1446(3) 0.4002(7) 0.047(2) Uani 1 1 d . . . H2 H 0.6089 0.1439 0.4562 0.056 Uiso 1 1 calc R . . C3' C 0.4710(15) 0.3872(3) 0.1691(7) 0.042(2) Uani 1 1 d . . . H3' H 0.3649 0.4104 0.2074 0.051 Uiso 1 1 calc R . . C3 C 0.3581(15) 0.2079(3) 0.3849(7) 0.047(2) Uani 1 1 d . . . H3 H 0.1926 0.2084 0.3308 0.056 Uiso 1 1 calc R . . C4 C 0.3613(16) 0.2336(4) 0.5123(8) 0.058(2) Uani 1 1 d . . . H4A H 0.3055 0.2741 0.5018 0.07 Uiso 1 1 calc R . . H4B H 0.5244 0.2335 0.5669 0.07 Uiso 1 1 calc R . . C4' C 0.3271(15) 0.3648(3) 0.0388(7) 0.048(2) Uani 1 1 d . . . H4' H 0.4355 0.3483 -0.0082 0.058 Uiso 1 1 calc R . . C5 C 0.2022(18) 0.1980(4) 0.5739(8) 0.067(3) Uani 1 1 d . . . H5A H 0.0373 0.2001 0.5193 0.08 Uiso 1 1 calc R . . C5' C 0.1491(17) 0.3187(3) 0.0544(8) 0.054(2) Uani 1 1 d . . . H5' H 0.0415 0.3356 0.1014 0.065 Uiso 1 1 calc R . . C6 C 0.2771(16) 0.1343(3) 0.5887(7) 0.059(3) Uani 1 1 d . . . H6A H 0.1647 0.1123 0.6233 0.071 Uiso 1 1 calc R . . H6B H 0.4347 0.1313 0.6486 0.071 Uiso 1 1 calc R . . C6' C 0.0023(18) 0.2938(5) -0.0711(9) 0.084(3) Uani 1 1 d . . . H61' H -0.0803 0.3251 -0.1264 0.1 Uiso 1 1 calc R . . H62' H 0.1046 0.2728 -0.1143 0.1 Uiso 1 1 calc R . . C7 C 0.3582(19) 0.0445(4) 0.4788(7) 0.051(2) Uani 1 1 d . . . C7' C 0.874(2) 0.3590(4) 0.4496(10) 0.065(3) Uani 1 1 d . . . C8 C 0.6788(19) -0.0240(4) 0.5137(10) 0.093(3) Uani 1 1 d . . . H8A H 0.8481 -0.0245 0.5208 0.139 Uiso 1 1 calc R . . H8B H 0.597 -0.0488 0.444 0.139 Uiso 1 1 calc R . . H8C H 0.6505 -0.0384 0.5916 0.139 Uiso 1 1 calc R . . C8' C 0.9153(18) 0.3659(4) 0.5901(8) 0.079(3) Uani 1 1 d . . . H81' H 0.7634 0.3677 0.6103 0.118 Uiso 1 1 calc R . . H82' H 1.0033 0.4016 0.6175 0.118 Uiso 1 1 calc R . . H83' H 1.0055 0.3328 0.6329 0.118 Uiso 1 1 calc R . . C9' C 0.6415(19) 0.4834(4) 0.1663(8) 0.060(3) Uani 1 1 d . . . C10' C 0.8535(17) 0.5147(4) 0.1395(10) 0.085(3) Uani 1 1 d . . . H10A H 0.9612 0.4862 0.1197 0.128 Uiso 1 1 calc R . . H10B H 0.9361 0.5369 0.2135 0.128 Uiso 1 1 calc R . . H10C H 0.7983 0.541 0.0684 0.128 Uiso 1 1 calc R . . C11' C 0.271(2) 0.4395(5) -0.1269(10) 0.079(4) Uani 1 1 d . . . C12' C 0.133(3) 0.4926(4) -0.1715(9) 0.123(5) Uani 1 1 d . . . H12A H 0.0109 0.4972 -0.1268 0.185 Uiso 1 1 calc R . . H12B H 0.0582 0.4893 -0.2615 0.185 Uiso 1 1 calc R . . H12C H 0.2371 0.5263 -0.1558 0.185 Uiso 1 1 calc R . . C13' C -0.199(2) 0.2005(5) -0.0942(9) 0.077(3) Uani 1 1 d . . . C14' C -0.3600(19) 0.1630(5) -0.0398(9) 0.102(4) Uani 1 1 d . . . H14A H -0.4028 0.184 0.0277 0.154 Uiso 1 1 calc R . . H14B H -0.2779 0.1271 -0.0066 0.154 Uiso 1 1 calc R . . H14C H -0.5027 0.1536 -0.1056 0.154 Uiso 1 1 calc R . . N1 N 0.449(2) 0.1216(3) 0.2722(9) 0.077(3) Uani 1 1 d . . . O2' O 0.6439(11) 0.3574(2) 0.3850(5) 0.0520(15) Uani 1 1 d . . . O2A O 0.2655(19) 0.1098(4) 0.1961(7) 0.125(4) Uani 1 1 d . . . O2B O 0.6516(16) 0.1167(4) 0.2562(7) 0.116(3) Uani 1 1 d . . . O3' O 0.6655(10) 0.4242(2) 0.1549(4) 0.0532(15) Uani 1 1 d . . . O3 O 0.5065(10) 0.2406(2) 0.3226(5) 0.0552(15) Uani 1 1 d . . . O4' O 0.1967(11) 0.4141(2) -0.0298(5) 0.0653(17) Uani 1 1 d . . . O5' O 0.2843(10) 0.2718(2) 0.1266(5) 0.0525(16) Uani 1 1 d . . . O5 O 0.2094(14) 0.2262(2) 0.6929(6) 0.104(3) Uani 1 1 d . . . H5 H 0.2553 0.2025 0.7514 0.155 Uiso 1 1 calc R . . O6' O -0.1704(11) 0.2534(3) -0.0388(5) 0.075(2) Uani 1 1 d . . . O7' O 1.0345(13) 0.3552(4) 0.3984(7) 0.103(2) Uani 1 1 d . . . O7A O 0.2255(12) 0.0054(3) 0.4879(7) 0.088(2) Uani 1 1 d . . . O7B O 0.5884(12) 0.0364(2) 0.4906(6) 0.0663(17) Uani 1 1 d . . . O9' O 0.4776(13) 0.5067(3) 0.1924(7) 0.095(3) Uani 1 1 d . . . O11' O 0.4393(17) 0.4202(4) -0.1596(7) 0.118(3) Uani 1 1 d . . . O13' O -0.1160(16) 0.1878(3) -0.1789(7) 0.129(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1' 0.060(6) 0.048(6) 0.054(6) 0.009(5) 0.031(5) -0.004(5) C1 0.047(6) 0.041(5) 0.057(6) 0.011(4) 0.013(5) -0.002(5) C2' 0.056(6) 0.043(5) 0.044(6) -0.008(4) 0.018(5) 0.007(5) C2 0.061(6) 0.036(5) 0.042(5) 0.002(4) 0.012(5) -0.001(5) C3' 0.044(5) 0.037(5) 0.047(5) 0.010(4) 0.015(4) -0.009(4) C3 0.052(6) 0.052(6) 0.048(5) 0.012(4) 0.032(5) 0.002(5) C4 0.073(7) 0.048(5) 0.063(6) 0.007(5) 0.035(5) 0.011(5) C4' 0.064(6) 0.037(5) 0.050(5) 0.009(4) 0.027(5) 0.008(5) C5 0.100(8) 0.056(6) 0.058(6) -0.008(5) 0.048(6) -0.005(6) C5' 0.080(7) 0.040(5) 0.050(6) 0.011(5) 0.028(5) -0.001(5) C6 0.090(7) 0.043(5) 0.055(6) 0.004(4) 0.039(5) -0.014(5) C6' 0.116(9) 0.093(7) 0.047(6) -0.009(6) 0.031(6) -0.046(8) C7 0.066(8) 0.038(6) 0.052(6) 0.002(4) 0.024(6) -0.009(6) C7' 0.080(8) 0.044(6) 0.074(7) -0.005(5) 0.023(7) 0.024(6) C8 0.095(8) 0.055(7) 0.148(10) 0.029(6) 0.067(7) 0.026(6) C8' 0.101(8) 0.082(7) 0.046(6) -0.008(5) 0.007(5) 0.007(6) C9' 0.067(8) 0.046(7) 0.069(6) 0.006(5) 0.022(6) -0.004(6) C10' 0.084(8) 0.054(6) 0.125(9) 0.009(6) 0.040(7) -0.011(6) C11' 0.098(10) 0.073(9) 0.054(7) 0.009(6) 0.001(7) -0.018(7) C12' 0.230(15) 0.049(7) 0.077(8) 0.018(6) 0.016(8) 0.001(9) C13' 0.104(8) 0.080(8) 0.044(6) 0.004(6) 0.016(6) -0.018(7) C14' 0.125(10) 0.097(8) 0.096(8) 0.000(7) 0.048(7) -0.053(8) N1 0.135(10) 0.043(5) 0.075(7) -0.004(4) 0.066(7) 0.010(6) O2' 0.052(4) 0.053(4) 0.052(4) 0.003(3) 0.017(3) 0.013(3) O2A 0.165(9) 0.145(8) 0.065(5) -0.043(5) 0.031(5) -0.058(7) O2B 0.160(8) 0.112(6) 0.107(6) 0.033(5) 0.091(6) 0.061(6) O3' 0.063(4) 0.038(3) 0.064(4) 0.006(3) 0.026(3) 0.001(3) O3 0.067(4) 0.044(3) 0.068(4) 0.020(3) 0.042(3) 0.006(3) O4' 0.087(5) 0.059(4) 0.051(4) 0.016(3) 0.019(3) 0.003(4) O5' 0.076(4) 0.044(3) 0.044(4) -0.004(3) 0.027(3) -0.010(3) O5 0.194(8) 0.058(4) 0.087(5) -0.001(4) 0.087(5) 0.005(5) O6' 0.089(5) 0.091(5) 0.048(4) -0.002(4) 0.023(4) -0.031(5) O7' 0.067(5) 0.146(7) 0.100(5) -0.022(5) 0.025(5) 0.021(5) O7A 0.057(5) 0.061(4) 0.147(7) 0.014(4) 0.030(5) -0.007(4) O7B 0.058(5) 0.045(4) 0.104(5) 0.027(3) 0.036(4) 0.010(3) O9' 0.090(6) 0.055(4) 0.161(8) -0.003(4) 0.073(5) 0.004(5) O11' 0.158(8) 0.124(7) 0.090(6) 0.051(5) 0.062(6) 0.003(7) O13' 0.199(9) 0.105(6) 0.117(6) -0.048(5) 0.099(6) -0.066(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1' O3 1.393(9) . ? C1' O5' 1.416(8) . ? C1' C2' 1.502(10) . ? C1' H1' 0.98 . ? C1 C7 1.476(11) . ? C1 C2 1.521(10) . ? C1 C6 1.536(9) . ? C1 H1 0.98 . ? C2' O2' 1.431(8) . ? C2' C3' 1.496(10) . ? C2' H2' 0.98 . ? C2 N1 1.491(10) . ? C2 C3 1.512(9) . ? C2 H2 0.98 . ? C3' O3' 1.442(8) . ? C3' C4' 1.526(10) . ? C3' H3' 0.98 . ? C3 O3 1.432(8) . ? C3 C4 1.497(10) . ? C3 H3 0.98 . ? C4 C5 1.504(10) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C4' O4' 1.439(9) . ? C4' C5' 1.505(10) . ? C4' H4' 0.98 . ? C5 O5 1.432(9) . ? C5 C6 1.503(10) . ? C5 H5A 0.98 . ? C5' O5' 1.424(8) . ? C5' C6' 1.510(10) . ? C5' H5' 0.98 . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C6' O6' 1.461(9) . ? C6' H61' 0.97 . ? C6' H62' 0.97 . ? C7 O7A 1.193(9) . ? C7 O7B 1.314(9) . ? C7' O7' 1.202(10) . ? C7' O2' 1.330(11) . ? C7' C8' 1.489(11) . ? C8 O7B 1.462(9) . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C8' H81' 0.96 . ? C8' H82' 0.96 . ? C8' H83' 0.96 . ? C9' O9' 1.181(10) . ? C9' O3' 1.356(9) . ? C9' C10' 1.508(11) . ? C10' H10A 0.96 . ? C10' H10B 0.96 . ? C10' H10C 0.96 . ? C11' O11' 1.200(11) . ? C11' O4' 1.368(11) . ? C11' C12' 1.453(13) . ? C12' H12A 0.96 . ? C12' H12B 0.96 . ? C12' H12C 0.96 . ? C13' O13' 1.180(10) . ? C13' O6' 1.333(11) . ? C13' C14' 1.490(12) . ? C14' H14A 0.96 . ? C14' H14B 0.96 . ? C14' H14C 0.96 . ? N1 O2A 1.190(10) . ? N1 O2B 1.230(10) . ? O5 H5 0.82 . ? _cod_database_code 7150000