#------------------------------------------------------------------------------ #$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201978 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/22/33/2223372.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_2223372 loop_ _publ_author_name 'Br\"uning, J\"urgen' 'Bats, Jan W.' 'Schmidt, Martin U.' _publ_section_title ; 2-Aminoterephthalic acid dimethyl ester ; _journal_coeditor_code FK2004 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2468 _journal_page_last o2469 _journal_paper_doi 10.1107/S1600536809036095 _journal_volume 65 _journal_year 2009 _chemical_formula_iupac 'C10 H11 N O4' _chemical_formula_moiety 'C10 H11 N O4' _chemical_formula_sum 'C10 H11 N O4' _chemical_formula_weight 209.20 _chemical_name_common ; Dimethyl-2-amino-terephthalate ; _chemical_name_systematic ; 2-Aminoterephthalic acid dimethyl ester ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 93.88(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.7721(12) _cell_length_b 16.928(5) _cell_length_c 11.841(5) _cell_measurement_reflns_used 57 _cell_measurement_temperature 166(2) _cell_measurement_theta_max 23 _cell_measurement_theta_min 3 _cell_volume 954.3(6) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'publCIF (Westrip, 2009)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 166(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens SMART 1K CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1400 _diffrn_reflns_av_sigmaI/netI 0.0958 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 11829 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.10 _diffrn_standards_decay_% 0.0 _diffrn_standards_interval_time 1200 _diffrn_standards_number 62 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.272 _refine_diff_density_min -0.241 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 1687 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.956 _refine_ls_R_factor_all 0.1149 _refine_ls_R_factor_gt 0.0543 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.06P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1169 _refine_ls_wR_factor_ref 0.1336 _reflns_number_gt 884 _reflns_number_total 1687 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fk2004.cif _cod_data_source_block I _cod_original_cell_volume 954.4(6) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2223372 _cod_database_fobs_code 2223372 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_site_type_symbol _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 O O1 -0.2268(4) 0.60319(11) 0.30114(17) 0.0341(6) Uani d . 1 . . O O2 -0.1912(5) 0.58551(12) 0.11612(18) 0.0421(7) Uani d . 1 . . O O3 0.7681(5) 0.32502(11) 0.44342(17) 0.0328(6) Uani d . 1 . . O O4 0.8629(4) 0.29952(12) 0.26489(18) 0.0333(6) Uani d . 1 . . N N1 0.5292(7) 0.36927(18) 0.0986(3) 0.0402(8) Uani d . 1 . . C C1 0.4228(7) 0.40860(18) 0.1867(3) 0.0280(8) Uani d . 1 . . C C2 0.2108(7) 0.46595(17) 0.1622(3) 0.0298(8) Uani d . 1 . . H H2A 0.1487 0.4762 0.0857 0.036 Uiso calc R 1 . . C C3 0.0944(6) 0.50678(17) 0.2471(3) 0.0258(8) Uani d . 1 . . C C4 0.1783(6) 0.49355(17) 0.3592(3) 0.0287(8) Uani d . 1 . . H H4A 0.0967 0.5224 0.4175 0.034 Uiso calc R 1 . . C C5 0.3823(6) 0.43779(17) 0.3851(2) 0.0277(8) Uani d . 1 . . H H5A 0.4401 0.4281 0.4622 0.033 Uiso calc R 1 . . C C6 0.5072(6) 0.39497(17) 0.3004(3) 0.0263(8) Uani d . 1 . . C C7 -0.1217(7) 0.56897(17) 0.2121(3) 0.0281(8) Uani d . 1 . . C C8 -0.4282(6) 0.66622(18) 0.2753(3) 0.0386(9) Uani d . 1 . . H H8A -0.3290 0.7134 0.2514 0.058 Uiso calc R 1 . . H H8B -0.5277 0.6785 0.3429 0.058 Uiso calc R 1 . . H H8C -0.5636 0.6492 0.2142 0.058 Uiso calc R 1 . . C C9 0.7296(7) 0.33575(17) 0.3320(3) 0.0267(8) Uani d . 1 . . C C10 0.9869(7) 0.26942(18) 0.4801(3) 0.0381(9) Uani d . 1 . . H H10A 0.9394 0.2170 0.4495 0.057 Uiso calc R 1 . . H H10B 1.0030 0.2670 0.5630 0.057 Uiso calc R 1 . . H H10C 1.1661 0.2867 0.4527 0.057 Uiso calc R 1 . . H H1A 0.702(9) 0.348(2) 0.120(3) 0.074(14) Uiso d . 1 . . H H1B 0.482(7) 0.385(2) 0.023(3) 0.059(12) Uiso d . 1 . . 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 0.0400(15) 0.0187(12) 0.0440(14) 0.0105(11) 0.0066(11) 0.0034(10) O2 0.0606(18) 0.0258(14) 0.0392(15) 0.0091(12) -0.0009(12) 0.0034(11) O3 0.0391(13) 0.0174(11) 0.0416(14) 0.0065(11) 0.0000(11) 0.0041(10) O4 0.0396(14) 0.0177(12) 0.0431(14) 0.0031(11) 0.0068(11) -0.0042(10) N1 0.049(2) 0.0357(19) 0.0361(19) 0.0125(16) 0.0027(17) -0.0045(15) C1 0.032(2) 0.0169(17) 0.0351(19) -0.0029(16) 0.0028(16) -0.0014(14) C2 0.034(2) 0.0208(18) 0.0347(19) -0.0019(16) 0.0017(16) 0.0027(15) C3 0.0273(19) 0.0148(17) 0.0354(19) -0.0035(15) 0.0038(15) 0.0009(14) C4 0.037(2) 0.0129(17) 0.036(2) -0.0012(16) 0.0058(16) -0.0015(14) C5 0.035(2) 0.0139(17) 0.0334(18) -0.0036(15) -0.0004(15) 0.0010(14) C6 0.0305(19) 0.0109(16) 0.0376(19) -0.0015(14) 0.0029(16) -0.0005(14) C7 0.034(2) 0.0133(18) 0.037(2) -0.0050(15) 0.0053(17) 0.0005(16) C8 0.040(2) 0.0197(19) 0.056(2) 0.0112(16) -0.0004(18) 0.0031(16) C9 0.035(2) 0.0127(17) 0.0329(19) -0.0090(15) 0.0039(16) -0.0007(14) C10 0.041(2) 0.0234(18) 0.049(2) 0.0059(17) -0.0031(17) 0.0051(17) 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 Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 O1 C8 . . 115.6(2) ? C9 O3 C10 . . 115.7(2) ? C1 N1 H1A . . 111(2) ? C1 N1 H1B . . 120(2) ? H1A N1 H1B . . 122(3) ? N1 C1 C6 . . 123.9(3) ? N1 C1 C2 . . 118.4(3) ? C6 C1 C2 . . 117.7(3) ? C3 C2 C1 . . 121.0(3) ? C3 C2 H2A . . 119.5 ? C1 C2 H2A . . 119.5 ? C2 C3 C4 . . 121.3(3) ? C2 C3 C7 . . 117.0(3) ? C4 C3 C7 . . 121.7(3) ? C5 C4 C3 . . 118.7(3) ? C5 C4 H4A . . 120.6 ? C3 C4 H4A . . 120.6 ? C4 C5 C6 . . 121.6(3) ? C4 C5 H5A . . 119.2 ? C6 C5 H5A . . 119.2 ? C1 C6 C5 . . 119.6(3) ? C1 C6 C9 . . 120.5(3) ? C5 C6 C9 . . 119.9(3) ? O2 C7 O1 . . 123.8(3) ? O2 C7 C3 . . 124.3(3) ? O1 C7 C3 . . 111.9(3) ? O1 C8 H8A . . 109.5 ? O1 C8 H8B . . 109.5 ? H8A C8 H8B . . 109.5 ? O1 C8 H8C . . 109.5 ? H8A C8 H8C . . 109.5 ? H8B C8 H8C . . 109.5 ? O4 C9 O3 . . 122.3(3) ? O4 C9 C6 . . 124.8(3) ? O3 C9 C6 . . 112.9(3) ? O3 C10 H10A . . 109.5 ? O3 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? O3 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? 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 O1 C7 . 1.330(3) ? O1 C8 . 1.455(3) ? O2 C7 . 1.195(3) ? O3 C9 . 1.333(3) ? O3 C10 . 1.450(3) ? O4 C9 . 1.216(3) ? N1 C1 . 1.365(4) ? N1 H1A . 0.92(4) ? N1 H1B . 0.94(3) ? C1 C6 . 1.398(4) ? C1 C2 . 1.418(4) ? C2 C3 . 1.368(4) ? C2 H2A . 0.9500 ? C3 C4 . 1.379(4) ? C3 C7 . 1.512(4) ? C4 C5 . 1.376(4) ? C4 H4A . 0.9500 ? C5 C6 . 1.403(4) ? C5 H5A . 0.9500 ? C6 C9 . 1.489(4) ? C8 H8A . 0.9800 ? C8 H8B . 0.9800 ? C8 H8C . 0.9800 ? C10 H10A . 0.9800 ? C10 H10B . 0.9800 ? C10 H10C . 0.9800 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _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 N1 H1A O4 . . 1_555 0.92(4) 2.01(4) 2.717(4) 133(3) yes N1 H1B O2 . . 3_565 0.95(4) 2.14(3) 3.016(4) 153(3) 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N1 C1 C2 C3 . . . . 179.4(3) ? C6 C1 C2 C3 . . . . 0.4(4) ? C1 C2 C3 C4 . . . . -0.1(4) ? C1 C2 C3 C7 . . . . 177.6(3) ? C2 C3 C4 C5 . . . . -0.3(4) ? C7 C3 C4 C5 . . . . -178.0(3) ? C3 C4 C5 C6 . . . . 0.5(4) ? N1 C1 C6 C5 . . . . -179.2(3) ? C2 C1 C6 C5 . . . . -0.1(4) ? N1 C1 C6 C9 . . . . 1.2(5) ? C2 C1 C6 C9 . . . . -179.8(3) ? C4 C5 C6 C1 . . . . -0.3(4) ? C4 C5 C6 C9 . . . . 179.3(3) ? C8 O1 C7 O2 . . . . -2.7(4) ? C8 O1 C7 C3 . . . . 177.5(2) ? C2 C3 C7 O2 . . . . -1.7(4) ? C4 C3 C7 O2 . . . . 176.1(3) ? C2 C3 C7 O1 . . . . 178.1(2) ? C4 C3 C7 O1 . . . . -4.1(4) ? C10 O3 C9 O4 . . . . 2.2(4) ? C10 O3 C9 C6 . . . . -178.6(2) ? C1 C6 C9 O4 . . . . 4.7(4) ? C5 C6 C9 O4 . . . . -175.0(3) ? C1 C6 C9 O3 . . . . -174.5(3) ? C5 C6 C9 O3 . . . . 5.8(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 71656