#------------------------------------------------------------------------------ #$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $ #$Revision: 326 $ #$URL: svn://www.crystallography.net/cod/cif/2/2205179.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_2205179 loop_ _publ_author_name 'Li, Xun' 'Xu, Wen-Fang' 'Wu, Ji-Feng' 'Wang, Jun-Li' 'Yuan, Yu-Mei' _publ_section_title ; (4S)-4-(Methoxycarbonylmethylaminocarbonyl)-4-(3,4,5- trimethoxybenzamido)butanoic acid ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o349 _journal_page_last o351 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C18 H24 N2 O9' _chemical_formula_moiety 'C18 H24 N2 O9' _chemical_formula_sum 'C18 H24 N2 O9' _chemical_formula_weight 412.39 _chemical_melting_point .442E-305 _chemical_name_systematic ; (4S)-4-(Methoxycarbonylmethylaminocarbonyl)-4-(3,4,5- trimethoxybenzamido)butanoic acid ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 98.401(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 27.665(9) _cell_length_b 5.1444(16) _cell_length_c 13.907(4) _cell_measurement_reflns_used 1522 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 21.961 _cell_measurement_theta_min 2.232 _cell_volume 1958.0(11) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9819 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_min 2.23 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 872 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.333 _refine_diff_density_min -0.197 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 267 _refine_ls_number_reflns 3619 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0606 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.7151P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1405 _refine_ls_wR_factor_ref 0.1546 _reflns_number_gt 2497 _reflns_number_total 3619 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wn6314.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; 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_type_symbol C1 0.31738(9) 0.8462(5) 1.07123(19) 0.0355(6) Uani d . 1 C H1A 0.2897 0.9431 1.0777 0.043 Uiso calc R 1 H C2 0.36107(10) 0.8945(5) 1.13138(19) 0.0367(7) Uani d . 1 C C3 0.32610(12) 1.2220(6) 1.2200(2) 0.0525(8) Uani d . 1 C H3A 0.3134 1.3122 1.1613 0.079 Uiso calc R 1 H H3B 0.3356 1.3458 1.2709 0.079 Uiso calc R 1 H H3C 0.3014 1.1090 1.2384 0.079 Uiso calc R 1 H C4 0.45221(14) 0.6629(9) 1.2670(3) 0.0831(13) Uani d . 1 C H4A 0.4259 0.7042 1.3022 0.125 Uiso calc R 1 H H4B 0.4827 0.7115 1.3049 0.125 Uiso calc R 1 H H4C 0.4522 0.4795 1.2542 0.125 Uiso calc R 1 H C5 0.40260(9) 0.7524(6) 1.1206(2) 0.0407(7) Uani d . 1 C C6 0.40048(10) 0.5643(6) 1.0483(2) 0.0419(7) Uani d . 1 C C7 0.44438(12) 0.2634(7) 0.9643(3) 0.0653(10) Uani d . 1 C H7A 0.4237 0.1183 0.9736 0.098 Uiso calc R 1 H H7B 0.4773 0.2036 0.9642 0.098 Uiso calc R 1 H H7C 0.4328 0.3456 0.9034 0.098 Uiso calc R 1 H C8 0.35650(9) 0.5099(6) 0.9899(2) 0.0388(7) Uani d . 1 C H8 0.3547 0.3789 0.9435 0.047 Uiso calc R 1 H C9 0.31536(9) 0.6530(5) 1.00163(18) 0.0315(6) Uani d . 1 C C10 0.26846(9) 0.5816(5) 0.93978(17) 0.0289(6) Uani d . 1 C C11 0.18944(8) 0.7257(5) 0.85856(17) 0.0269(6) Uani d . 1 C H11 0.1921 0.5768 0.8157 0.032 Uiso calc R 1 H C12 0.17095(9) 0.9580(5) 0.79693(19) 0.0343(6) Uani d . 1 C H12A 0.1371 0.9265 0.7697 0.041 Uiso calc R 1 H H12B 0.1715 1.1088 0.8390 0.041 Uiso calc R 1 H C13 0.19905(10) 1.0222(5) 0.71492(19) 0.0364(7) Uani d . 1 C H13A 0.2326 1.0641 0.7410 0.044 Uiso calc R 1 H H13B 0.1993 0.8726 0.6725 0.044 Uiso calc R 1 H C14 0.17601(10) 1.2476(5) 0.65829(18) 0.0311(6) Uani d . 1 C C15 0.15135(9) 0.6651(5) 0.92317(18) 0.0294(6) Uani d . 1 C C16 0.07441(10) 0.4562(6) 0.9360(2) 0.0472(8) Uani d . 1 C H16A 0.0574 0.6193 0.9417 0.057 Uiso calc R 1 H H16B 0.0853 0.3912 1.0010 0.057 Uiso calc R 1 H C17 0.04017(10) 0.2651(6) 0.8817(2) 0.0390(7) Uani d . 1 C C18 -0.03991(12) 0.0996(8) 0.8654(3) 0.0756(12) Uani d . 1 C H18A -0.0483 0.1578 0.7995 0.113 Uiso calc R 1 H H18B -0.0682 0.1087 0.8979 0.113 Uiso calc R 1 H H18C -0.0285 -0.0768 0.8658 0.113 Uiso calc R 1 H N1 0.23689(7) 0.7748(4) 0.91463(14) 0.0306(5) Uani d . 1 N H1 0.2449 0.9312 0.9321 0.037 Uiso calc R 1 H N2 0.11623(7) 0.5008(4) 0.88709(15) 0.0327(5) Uani d . 1 N H2 0.1185 0.4198 0.8338 0.039 Uiso calc R 1 H O1 0.44343(7) 0.4434(5) 1.04041(17) 0.0631(7) Uani d . 1 O O2 0.44611(7) 0.8005(5) 1.17804(16) 0.0583(6) Uani d . 1 O O3 0.36722(7) 1.0733(4) 1.20430(14) 0.0526(6) Uani d . 1 O O4 0.25945(7) 0.3569(4) 0.91342(14) 0.0420(5) Uani d . 1 O O5 0.19976(8) 1.3243(4) 0.58779(15) 0.0544(6) Uani d . 1 O H5 0.1865 1.4539 0.5617 0.082 Uiso calc R 1 H O6 0.13979(8) 1.3549(4) 0.67562(14) 0.0540(6) Uani d . 1 O O7 0.15089(7) 0.7706(4) 1.00235(13) 0.0448(5) Uani d . 1 O O8 0.04948(8) 0.1342(5) 0.81607(17) 0.0641(7) Uani d . 1 O O9 -0.00192(7) 0.2632(5) 0.91513(15) 0.0617(7) Uani d . 1 O 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 0.0260(14) 0.0374(16) 0.0420(15) 0.0020(12) 0.0010(12) 0.0016(13) C2 0.0345(16) 0.0346(16) 0.0386(15) -0.0030(13) -0.0020(12) -0.0007(12) C3 0.056(2) 0.053(2) 0.0469(17) 0.0067(16) 0.0003(15) -0.0082(15) C4 0.060(2) 0.108(3) 0.072(3) 0.010(2) -0.024(2) 0.018(2) C5 0.0247(15) 0.0491(18) 0.0453(16) -0.0018(13) -0.0050(12) 0.0042(14) C6 0.0259(15) 0.0440(18) 0.0553(18) 0.0067(13) 0.0043(13) 0.0039(15) C7 0.046(2) 0.063(2) 0.090(3) 0.0151(17) 0.0175(18) -0.009(2) C8 0.0292(15) 0.0406(17) 0.0459(16) 0.0030(13) 0.0028(12) -0.0022(13) C9 0.0249(14) 0.0317(15) 0.0368(14) 0.0007(11) 0.0010(11) 0.0054(12) C10 0.0260(14) 0.0280(15) 0.0326(14) -0.0006(11) 0.0037(11) 0.0032(11) C11 0.0233(13) 0.0266(14) 0.0298(13) 0.0010(11) 0.0002(10) -0.0009(11) C12 0.0264(14) 0.0356(15) 0.0400(15) 0.0009(12) 0.0020(11) 0.0047(12) C13 0.0340(15) 0.0376(16) 0.0376(15) 0.0044(13) 0.0055(12) 0.0049(12) C14 0.0288(14) 0.0340(15) 0.0298(13) 0.0011(12) 0.0017(11) -0.0024(12) C15 0.0293(14) 0.0261(14) 0.0314(14) -0.0005(11) -0.0004(11) -0.0016(11) C16 0.0385(17) 0.057(2) 0.0485(17) -0.0155(15) 0.0132(14) -0.0138(15) C17 0.0326(16) 0.0436(17) 0.0421(16) -0.0069(13) 0.0096(13) -0.0013(14) C18 0.041(2) 0.107(3) 0.080(2) -0.039(2) 0.0121(17) -0.031(2) N1 0.0228(11) 0.0264(12) 0.0393(12) -0.0036(9) -0.0057(9) -0.0026(10) N2 0.0278(12) 0.0331(13) 0.0379(12) -0.0066(10) 0.0068(9) -0.0090(10) O1 0.0300(12) 0.0767(16) 0.0807(16) 0.0146(11) 0.0013(10) -0.0128(13) O2 0.0310(11) 0.0738(16) 0.0642(14) -0.0087(11) -0.0123(10) 0.0009(12) O3 0.0457(13) 0.0549(13) 0.0525(13) 0.0042(10) -0.0091(10) -0.0157(11) O4 0.0395(11) 0.0279(11) 0.0550(12) -0.0008(9) -0.0045(9) -0.0026(9) O5 0.0575(14) 0.0590(15) 0.0513(13) 0.0170(11) 0.0232(11) 0.0232(11) O6 0.0457(13) 0.0663(15) 0.0522(13) 0.0203(11) 0.0146(10) 0.0200(11) O7 0.0486(12) 0.0497(13) 0.0377(11) -0.0159(10) 0.0121(9) -0.0124(9) O8 0.0490(14) 0.0708(16) 0.0763(16) -0.0225(12) 0.0222(12) -0.0308(13) O9 0.0399(13) 0.0838(17) 0.0648(14) -0.0269(12) 0.0191(10) -0.0286(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C9 1.383(4) C1 C2 1.388(4) C1 H1A 0.9300 C2 O3 1.361(3) C2 C5 1.388(4) C3 O3 1.414(4) C3 H3A 0.9600 C3 H3B 0.9600 C3 H3C 0.9600 C4 O2 1.414(4) C4 H4A 0.9600 C4 H4B 0.9600 C4 H4C 0.9600 C5 O2 1.366(3) C5 C6 1.391(4) C6 O1 1.360(3) C6 C8 1.389(4) C7 O1 1.409(4) C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 0.9600 C8 C9 1.385(4) C8 H8 0.9300 C9 C10 1.494(3) C10 O4 1.227(3) C10 N1 1.336(3) C11 N1 1.448(3) C11 C15 1.514(3) C11 C12 1.516(3) C11 H11 0.9800 C12 C13 1.508(4) C12 H12A 0.9700 C12 H12B 0.9700 C13 C14 1.491(4) C13 H13A 0.9700 C13 H13B 0.9700 C14 O6 1.199(3) C14 O5 1.318(3) C15 O7 1.229(3) C15 N2 1.330(3) C16 N2 1.443(3) C16 C17 1.491(4) C16 H16A 0.9700 C16 H16B 0.9700 C17 O8 1.193(3) C17 O9 1.315(3) C18 O9 1.442(4) C18 H18A 0.9600 C18 H18B 0.9600 C18 H18C 0.9600 N1 H1 0.8600 N2 H2 0.8600 O5 H5 0.8200 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C9 C1 C2 119.5(2) C9 C1 H1A 120.2 C2 C1 H1A 120.2 O3 C2 C5 114.9(2) O3 C2 C1 124.9(3) C5 C2 C1 120.2(3) O3 C3 H3A 109.5 O3 C3 H3B 109.5 H3A C3 H3B 109.5 O3 C3 H3C 109.5 H3A C3 H3C 109.5 H3B C3 H3C 109.5 O2 C4 H4A 109.5 O2 C4 H4B 109.5 H4A C4 H4B 109.5 O2 C4 H4C 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 O2 C5 C2 120.9(3) O2 C5 C6 119.3(3) C2 C5 C6 119.7(2) O1 C6 C8 124.2(3) O1 C6 C5 115.5(2) C8 C6 C5 120.2(3) O1 C7 H7A 109.5 O1 C7 H7B 109.5 H7A C7 H7B 109.5 O1 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 C9 C8 C6 119.3(3) C9 C8 H8 120.4 C6 C8 H8 120.4 C1 C9 C8 121.0(2) C1 C9 C10 121.5(2) C8 C9 C10 117.5(2) O4 C10 N1 121.7(2) O4 C10 C9 121.7(2) N1 C10 C9 116.6(2) N1 C11 C15 111.80(19) N1 C11 C12 111.8(2) C15 C11 C12 106.9(2) N1 C11 H11 108.7 C15 C11 H11 108.7 C12 C11 H11 108.7 C13 C12 C11 115.6(2) C13 C12 H12A 108.4 C11 C12 H12A 108.4 C13 C12 H12B 108.4 C11 C12 H12B 108.4 H12A C12 H12B 107.4 C14 C13 C12 110.0(2) C14 C13 H13A 109.7 C12 C13 H13A 109.7 C14 C13 H13B 109.7 C12 C13 H13B 109.7 H13A C13 H13B 108.2 O6 C14 O5 122.3(2) O6 C14 C13 123.9(2) O5 C14 C13 113.9(2) O7 C15 N2 121.1(2) O7 C15 C11 122.7(2) N2 C15 C11 116.1(2) N2 C16 C17 111.1(2) N2 C16 H16A 109.4 C17 C16 H16A 109.4 N2 C16 H16B 109.4 C17 C16 H16B 109.4 H16A C16 H16B 108.0 O8 C17 O9 124.6(3) O8 C17 C16 124.6(3) O9 C17 C16 110.9(2) O9 C18 H18A 109.5 O9 C18 H18B 109.5 H18A C18 H18B 109.5 O9 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C10 N1 C11 121.2(2) C10 N1 H1 119.4 C11 N1 H1 119.4 C15 N2 C16 121.0(2) C15 N2 H2 119.5 C16 N2 H2 119.5 C6 O1 C7 118.3(2) C5 O2 C4 113.8(3) C2 O3 C3 117.7(2) C14 O5 H5 109.5 C17 O9 C18 117.1(2) 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 C9 C1 C2 O3 -177.9(2) C9 C1 C2 C5 1.0(4) O3 C2 C5 O2 -2.2(4) C1 C2 C5 O2 178.8(3) O3 C2 C5 C6 180.0(3) C1 C2 C5 C6 1.0(4) O2 C5 C6 O1 -0.7(4) C2 C5 C6 O1 177.1(3) O2 C5 C6 C8 179.2(3) C2 C5 C6 C8 -3.0(4) O1 C6 C8 C9 -177.3(3) C5 C6 C8 C9 2.9(4) C2 C1 C9 C8 -1.1(4) C2 C1 C9 C10 175.8(2) C6 C8 C9 C1 -0.8(4) C6 C8 C9 C10 -177.8(2) C1 C9 C10 O4 -145.4(3) C8 C9 C10 O4 31.6(4) C1 C9 C10 N1 34.6(3) C8 C9 C10 N1 -148.4(2) N1 C11 C12 C13 67.7(3) C15 C11 C12 C13 -169.7(2) C11 C12 C13 C14 178.0(2) C12 C13 C14 O6 -1.6(4) C12 C13 C14 O5 177.0(2) N1 C11 C15 O7 35.9(3) C12 C11 C15 O7 -86.8(3) N1 C11 C15 N2 -147.8(2) C12 C11 C15 N2 89.5(3) N2 C16 C17 O8 11.5(4) N2 C16 C17 O9 -167.6(3) O4 C10 N1 C11 2.9(4) C9 C10 N1 C11 -177.2(2) C15 C11 N1 C10 88.9(3) C12 C11 N1 C10 -151.3(2) O7 C15 N2 C16 4.9(4) C11 C15 N2 C16 -171.4(2) C17 C16 N2 C15 179.9(2) C8 C6 O1 C7 4.3(5) C5 C6 O1 C7 -175.8(3) C2 C5 O2 C4 86.9(4) C6 C5 O2 C4 -95.3(4) C5 C2 O3 C3 -179.1(3) C1 C2 O3 C3 -0.2(4) O8 C17 O9 C18 -3.0(5) C16 C17 O9 C18 176.1(3) 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 O5 H5 O7 4_585 0.82 1.85 2.667(3) 174 N2 H2 O6 1_545 0.86 2.38 3.193(3) 157 N1 H1 O4 1_565 0.86 2.25 3.060(3) 157 C11 H11 O6 1_545 0.98 2.52 3.313(3) 138 C18 H18B O6 2_536 0.96 2.47 3.014(4) 116