#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011960.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011960 loop_ _publ_author_name 'Renaudet, Olivier' 'Dumy, Pascal' 'Philouze, Christian' 'Averbuch-Pouchot, Marie-Th\'er\`ese' _publ_section_title N-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-\a-D-galactopyranosyloxy)succinimide _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 649 _journal_page_last 650 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C18 H24 N2 O11' _chemical_formula_sum 'C18 H24 N2 O11' _chemical_formula_weight 444.39 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90 _cell_angle_beta 114.28(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.556(4) _cell_length_b 9.1910(10) _cell_length_c 12.536(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 26.78 _cell_measurement_theta_min 20.22 _cell_volume 1108.7(8) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1992-1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 293 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .009 _diffrn_reflns_av_sigmaI/netI .040 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3547 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 29.97 _diffrn_reflns_theta_min 2.12 _diffrn_standards_decay_% 5.51 _diffrn_standards_interval_count 120 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .111 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description 'monoclinic prism' _exptl_crystal_F_000 468 _exptl_crystal_size_max .38 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .34 _refine_diff_density_max .25 _refine_diff_density_min -.19 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.939 _refine_ls_goodness_of_fit_ref 1.939 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 279 _refine_ls_number_reflns 2900 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .069 _refine_ls_R_factor_gt .069 _refine_ls_shift/su_max .030 _refine_ls_shift/su_mean .008 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.0002|Fo|^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_all .055 _refine_ls_wR_factor_ref .055 _reflns_number_gt 2900 _reflns_number_total 3470 _reflns_threshold_expression I>0.07\s(I) _[local]_cod_data_source_file da1176.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_original_cell_volume 1108.6(7) _cod_database_code 2011960 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' 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_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy O1 -.28040(10) -.5525 -.98523(9) .0574(3) Uani d ? . 1.000 O3 .12460(10) -.60800(10) -.72175(9) .0529(3) Uani d ? . 1.000 O4 .02090(10) -.36350(10) -.65250(9) .0560(3) Uani d ? . 1.000 O5 -.23420(10) -.35640(10) -.85519(8) .0510(3) Uani d ? . 1.000 O6 -.40310(10) -.3098(2) -.73150(10) .0692(4) Uani d ? . 1.000 O7 -.5199(2) -.5766(3) -.9433(2) .1307(7) Uani d ? . 1.000 O8 -.3494(2) -.4554(3) -1.20950(10) .1364(7) Uani d ? . 1.000 O9 .0420(2) -.35470(10) -1.03890(10) .0851(4) Uani d ? . 1.000 O10 .08220(10) -.7987(2) -.63000(10) .0754(4) Uani d ? . 1.000 O11 .1505(2) -.4715(2) -.48170(10) .0993(5) Uani d ? . 1.000 O12 -.4488(2) -.5150(2) -.6609(2) .1043(5) Uani d ? . 1.000 N1 -.4113(2) -.5083(2) -1.05980(10) .0722(4) Uani d ? . 1.000 N2 -.01500(10) -.55640(10) -.97040(10) .0490(3) Uani d ? . 1.000 C1 -.1936(2) -.4268(2) -.93450(10) .0487(4) Uani d ? . 1.000 C2 -.0467(2) -.4825(2) -.88260(10) .0453(4) Uani d ? . 1.000 C3 -.0214(2) -.5760(2) -.77600(10) .0458(4) Uani d ? . 1.000 C4 -.0653(2) -.4917(2) -.69200(10) .0479(4) Uani d ? . 1.000 C5 -.2139(2) -.4398(2) -.75220(10) .0502(4) Uani d ? . 1.000 C6 -.2567(2) -.3432(2) -.67660(10) .0613(5) Uani d ? . 1.000 C7 -.5232(2) -.5258(3) -1.0315(2) .1035(8) Uani d ? . 1.000 C8 -.6434(3) -.4686(4) -1.1371(3) .1560(10) Uani d ? . 1.000 C9 -.5863(4) -.4200(4) -1.2241(3) .1640(10) Uani d ? . 1.000 C10 -.4367(3) -.4611(3) -1.1721(2) .1064(7) Uani d ? . 1.000 C11 .0160(2) -.4850(2) -1.04800(10) .0563(4) Uani d ? . 1.000 C12 .0113(3) -.5700(2) -1.1514(2) .0858(6) Uani d ? . 1.000 C13 .1639(2) -.7240(2) -.64770(10) .0578(4) Uani d ? . 1.000 C14 .3160(2) -.7380(3) -.5940(2) .0814(6) Uani d ? . 1.000 C15 .1261(2) -.3677(3) -.5452(2) .0722(5) Uani d ? . 1.000 C16 .2027(3) -.2266(3) -.5205(2) .1112(8) Uani d ? . 1.000 C17 -.4899(2) -.4077(3) -.7189(2) .0777(6) Uani d ? . 1.000 C18 -.6375(2) -.3638(4) -.7819(2) .1043(8) Uani d ? . 1.000 H1 -.2032 -.3608 -.9957 .059 Uiso c ? . 1.000 H2 .0133 -.4008 -.8570 .055 Uiso c ? . 1.000 H3 -.0731 -.6636 -.7991 .055 Uiso c ? . 1.000 H4 -.0549 -.5513 -.6269 .058 Uiso c ? . 1.000 H5 -.2736 -.5222 -.7746 .060 Uiso c ? . 1.000 H6 -.2054 -.2554 -.6626 .073 Uiso c ? . 1.000 H7 -.2373 -.3913 -.6045 .073 Uiso c ? . 1.000 H8 -.6842 -.3880 -1.1158 .190 Uiso c ? . 1.000 H9 -.7104 -.5427 -1.1701 .190 Uiso c ? . 1.000 H10 -.5965 -.3187 -1.2365 .198 Uiso c ? . 1.000 H11 -.6333 -.4697 -1.2968 .198 Uiso c ? . 1.000 H12 -.0130 -.6677 -1.1447 .105 Uiso c ? . 1.000 H13 -.0556 -.5282 -1.2210 .105 Uiso c ? . 1.000 H14 .1003 -.5671 -1.1535 .105 Uiso c ? . 1.000 H15 -.0295 -.6452 -.9790 .115 Uiso c ? . 1.000 H16 .3560 -.6524 -.5509 .099 Uiso c ? . 1.000 H17 .3418 -.8196 -.5428 .099 Uiso c ? . 1.000 H18 .3488 -.7513 -.6535 .099 Uiso c ? . 1.000 H19 .1410 -.1497 -.5241 .135 Uiso c ? . 1.000 H20 .2391 -.2104 -.5776 .135 Uiso c ? . 1.000 H21 .2768 -.2294 -.4451 .135 Uiso c ? . 1.000 H22 -.6958 -.4358 -.7715 .127 Uiso c ? . 1.000 H23 -.6523 -.2734 -.7521 .127 Uiso c ? . 1.000 H24 -.6588 -.3538 -.8631 .127 Uiso c ? . 1.000 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 O1 .0593(6) .0465(6) .0500(6) -.0088(5) .0061(5) -.0044(6) O3 .0549(5) .0443(6) .0534(5) .0026(5) .0163(4) .0087(5) O4 .0584(6) .0501(6) .0474(5) -.0068(6) .0096(4) -.0073(5) O5 .0567(6) .0435(6) .0468(5) .0040(5) .0150(4) .0013(5) O6 .0630(6) .0717(9) .0715(7) .0117(6) .0261(5) .0094(7) O7 .0900(10) .188(2) .1200(10) -.0430(10) .0493(8) -.0380(10) O8 .166(2) .161(2) .0608(8) -.034(2) .0249(9) .0220(10) O9 .1550(10) .0272(5) .1010(8) -.0100(7) .0808(6) .0012(6) O10 .0874(8) .0574(8) .0747(7) .0017(7) .0267(6) .0233(7) O11 .0980(10) .1030(10) .0586(7) .0060(10) -.0071(7) .0016(8) O12 .0809(9) .1030(10) .1210(10) .0064(9) .0335(8) .0488(9) N1 .0636(8) .0700(10) .0560(7) -.0052(8) -.0028(6) -.0086(8) N2 .0730(8) .0255(6) .0500(6) -.0002(6) .0268(5) -.0014(5) C1 .0624(8) .0353(8) .0405(7) -.0026(7) .0133(6) .0033(7) C2 .0572(8) .0297(7) .0454(7) -.0078(7) .0174(6) -.0004(6) C3 .0510(7) .0354(8) .0431(7) -.0048(7) .0113(6) .0023(6) C4 .0521(8) .0452(9) .0417(7) -.0047(7) .0145(6) .0023(7) C5 .0516(8) .0505(9) .0428(7) -.0056(7) .0135(6) .0009(7) C6 .0613(8) .0660(10) .0545(8) .0022(9) .0212(7) -.0032(9) C7 .0650(10) .118(2) .1110(10) -.0240(10) .0200(10) -.0480(10) C8 .070(2) .145(3) .176(2) .011(2) -.0270(10) -.051(2) C9 .129(2) .109(2) .132(2) -.009(2) -.068(2) .015(2) C10 .127(2) .084(2) .0550(10) -.013(2) -.0160(10) .0000(10) C11 .0810(10) .0288(7) .0647(8) .0099(8) .0361(7) .0070(7) C12 .154(2) .0450(10) .0860(10) .0120(10) .0771(9) .0004(9) C13 .0785(9) .0475(9) .0432(7) .0152(8) .0207(7) .0082(7) C14 .0840(10) .0830(10) .0770(10) .0290(10) .0323(9) .0230(10) C15 .0610(10) .0830(10) .0563(9) -.0020(10) .0072(7) -.0239(9) C16 .107(2) .089(2) .106(2) -.0300(10) .0110(10) -.0390(10) C17 .0674(9) .0890(10) .0790(10) .0020(10) .0328(8) .0060(10) C18 .0680(10) .112(2) .132(2) .0150(10) .0400(10) .023(2) 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 O1 N1 . . 1.373(2) yes O1 C1 . . 1.449(2) yes O3 C3 . . 1.436(3) yes O3 C13 . . 1.362(3) yes O4 C4 . . 1.446(3) yes O4 C15 . . 1.347(3) yes O5 C1 . . 1.394(3) yes O5 C5 . . 1.440(3) yes O6 C6 . . 1.443(3) yes O6 C17 . . 1.339(4) yes O7 C7 . . 1.189(5) n O8 C10 . . 1.195(5) n O9 C11 . . 1.223(3) n O10 C13 . . 1.192(3) n O11 C15 . . 1.201(4) n O12 C17 . . 1.196(4) n N1 C7 . . 1.375(5) yes N1 C10 . . 1.390(4) yes N2 C2 . . 1.444(3) yes N2 C11 . . 1.322(3) yes C1 C2 . . 1.503(3) yes C2 C3 . . 1.518(3) yes C3 C4 . . 1.525(3) yes C4 C5 . . 1.511(3) yes C5 C6 . . 1.497(4) yes C7 C8 . . 1.502(5) n C8 C9 . . 1.514(8) n C9 C10 . . 1.488(6) n C11 C12 . . 1.496(4) n C13 C14 . . 1.469(4) n C15 C16 . . 1.492(5) n C17 C18 . . 1.484(4) n N2 H15 . . .83 no C1 H1 . . .95 no C2 H2 . . .95 no C3 H3 . . .95 no C4 H4 . . .95 no C5 H5 . . .95 no C6 H6 . . .95 no C6 H7 . . .95 no C8 H8 . . .95 no C8 H9 . . .95 no C9 H10 . . .94 no C9 H11 . . .96 no C12 H12 . . .95 no C12 H13 . . .95 no C12 H14 . . .95 no C14 H16 . . .95 no C14 H17 . . .95 no C14 H18 . . .95 no C16 H19 . . .95 no C16 H20 . . .95 no C16 H21 . . .95 no C18 H22 . . .95 no C18 H23 . . .95 no C18 H24 . . .95 no loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .002 .002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O .008 .006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N .004 .003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H .000 .000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 1 3 3 -1 3 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag N1 O1 C1 109.90(10) yes C3 O3 C13 116.8(2) yes C4 O4 C15 117.6(2) yes C1 O5 C5 114.7(2) yes C6 O6 C17 116.8(2) yes O1 N1 C7 121.4(2) yes O1 N1 C10 120.2(3) yes C7 N1 C10 118.0(3) yes C2 N2 C11 122.2(2) yes O1 C1 O5 111.0(2) yes O1 C1 C2 105.8(2) yes O5 C1 C2 114.5(2) yes N2 C2 C1 110.6(2) yes N2 C2 C3 113.1(2) yes C1 C2 C3 110.5(2) yes O3 C3 C2 107.4(2) yes O3 C3 C4 110.4(2) yes C2 C3 C4 109.1(2) yes O4 C4 C3 108.8(2) yes O4 C4 C5 106.9(2) yes C3 C4 C5 111.3(2) yes O5 C5 C4 110.9(2) yes O5 C5 C6 106.2(2) yes C4 C5 C6 113.1(2) yes O6 C6 C5 111.5(2) yes O7 C7 N1 125.9(3) n O7 C7 C8 130.4(4) n N1 C7 C8 103.7(4) n C7 C8 C9 107.2(4) n C8 C9 C10 105.9(3) n O8 C10 N1 123.5(3) n O8 C10 C9 131.9(4) n N1 C10 C9 104.5(4) n O9 C11 N2 122.1(2) n O9 C11 C12 121.2(2) n N2 C11 C12 116.6(2) n O3 C13 O10 122.4(2) n O3 C13 C14 110.5(2) n O10 C13 C14 127.1(2) n O4 C15 O11 123.3(3) n O4 C15 C16 109.7(3) n O11 C15 C16 127.0(2) n O6 C17 O12 122.1(3) n O6 C17 C18 111.9(3) n O12 C17 C18 125.9(3) n C2 N2 H15 118.3 no C11 N2 H15 118.8 no O1 C1 H1 108.5 no O5 C1 H1 108.5 no C2 C1 H1 108.4 no N2 C2 H2 107.4 no C1 C2 H2 107.6 no C3 C2 H2 107.4 no O3 C3 H3 109.9 no C2 C3 H3 110.0 no C4 C3 H3 110.0 no O4 C4 H4 109.9 no C3 C4 H4 109.9 no C5 C4 H4 109.9 no O5 C5 H5 108.8 no C4 C5 H5 108.7 no C6 C5 H5 108.9 no O6 C6 H6 109.0 no O6 C6 H7 108.8 no C5 C6 H6 109.0 no C5 C6 H7 108.8 no H6 C6 H7 109.7 no C7 C8 H8 110.0 no C7 C8 H9 110.0 no C9 C8 H8 109.5 no C9 C8 H9 110.2 no H8 C8 H9 109.9 no C8 C9 H10 111.0 no C8 C9 H11 110.0 no C10 C9 H10 110.6 no C10 C9 H11 109.7 no H10 C9 H11 109.5 no C11 C12 H12 109.4 no C11 C12 H13 109.4 no C11 C12 H14 109.1 no H12 C12 H13 109.8 no H12 C12 H14 109.6 no H13 C12 H14 109.4 no C13 C14 H16 109.6 no C13 C14 H17 109.5 no C13 C14 H18 109.5 no H16 C14 H17 109.4 no H16 C14 H18 109.5 no H17 C14 H18 109.4 no C15 C16 H19 109.6 no C15 C16 H20 109.3 no C15 C16 H21 109.8 no H19 C16 H20 109.1 no H19 C16 H21 109.7 no H20 C16 H21 109.3 no C17 C18 H22 109.6 no C17 C18 H23 109.6 no C17 C18 H24 109.3 no H22 C18 H23 109.5 no H22 C18 H24 109.5 no H23 C18 H24 109.4 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O3 O9 3.591(2) 2_543 no O4 C12 3.571(3) 2_553 no O5 C12 3.509(4) 2_553 no O6 C10 3.593(4) 2_453 no O8 C14 3.301(4) 2_553 no O9 N2 2.764(2) 2_553 no O9 C3 3.402(3) 2_553 no O9 C2 3.565(3) 2_553 no O9 C18 3.587(4) 1_655 no O10 C12 3.533(3) 2_543 no O10 C6 3.537(3) 2_544 no O11 C9 3.315(4) 1_656 no O12 C16 3.293(4) 2_544 no O12 C14 3.575(4) 1_455 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H15 O9 2_543 .83 1.95 2.764(2) 167.2 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag O1 N1 C7 O7 1.1(6) no O1 N1 C7 C8 -178.1(3) no O1 N1 C10 O8 -.4(6) no O1 N1 C10 C9 -178.7(3) no O1 C1 O5 C5 65.9(2) no O1 C1 C2 N2 56.2(2) no O1 C1 C2 C3 -69.9(2) no O3 C3 C2 N2 63.4(2) no O3 C3 C2 C1 -172.0(2) no O3 C3 C4 O4 54.9(2) no O3 C3 C4 C5 172.5(2) no O4 C4 C3 C2 -62.9(2) no O4 C4 C5 O5 64.1(2) no O4 C4 C5 C6 -55.1(2) no O5 C1 O1 N1 70.5(2) no O5 C1 C2 N2 178.7(2) no O5 C1 C2 C3 52.6(2) no O5 C5 C4 C3 -54.6(2) no O5 C5 C6 O6 64.9(3) no O6 C6 C5 C4 -173.2(2) no O7 C7 N1 C10 173.2(4) no O7 C7 C8 C9 -178.9(5) no O8 C10 N1 C7 -172.7(4) no O8 C10 C9 C8 174.2(5) no O9 C11 N2 C2 12.2(4) no O10 C13 O3 C3 1.8(3) no O11 C15 O4 C4 -.5(4) no O12 C17 O6 C6 3.1(4) no N1 O1 C1 C2 -164.7(2) no N1 C7 C8 C9 .3(5) no N1 C10 C9 C8 -7.7(5) no N2 C2 C3 C4 -176.9(2) no C1 O1 N1 C7 -108.8(3) no C1 O1 N1 C10 79.2(3) no C1 O5 C5 C4 53.9(2) no C1 O5 C5 C6 177.2(2) no C1 C2 N2 C11 79.0(2) no C1 C2 C3 C4 -52.3(2) no C2 N2 C11 C12 -165.0(2) no C2 C1 O5 C5 -53.7(2) no C2 C3 O3 C13 -160.5(2) no C2 C3 C4 C5 54.7(2) no C3 O3 C13 C14 -176.7(2) no C3 C2 N2 C11 -156.4(2) no C3 C4 O4 C15 -101.4(2) no C3 C4 C5 C6 -173.9(2) no C4 O4 C15 C16 179.9(2) no C4 C3 O3 C13 80.6(2) no C5 C4 O4 C15 138.3(2) no C5 C6 O6 C17 83.7(3) no C6 O6 C17 C18 -178.2(3) no C7 N1 C10 C9 9.0(4) no C7 C8 C9 C10 4.7(5) no C8 C7 N1 C10 -6.0(4) no _cod_database_fobs_code 2011960