#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/51/2205199.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_2205199 loop_ _publ_author_name 'Pinkus, A. G.' 'Klausmeyer, Kevin K.' 'Feazell, Rodney P.' 'Lin, Ellen C. H. Y.' _publ_section_title ; Ethyl 2,3,5,6-tetramethylbenzoate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o662 _journal_page_last o663 _journal_paper_doi 10.1107/S1600536805004319 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C13 H18 O2' _chemical_formula_moiety 'C13 H18 O2' _chemical_formula_sum 'C13 H18 O2' _chemical_formula_weight 206.27 _chemical_name_systematic ; Ethyl 2,3,5,6-tetramethylbenzoate ; _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 SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 101.725(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 18.2230(10) _cell_length_b 5.5837(4) _cell_length_c 11.5842(7) _cell_measurement_reflns_used 2643 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 27.68 _cell_measurement_theta_min 2.28 _cell_volume 1154.12(13) _computing_cell_refinement 'APEX2 (Bruker, 2003)' _computing_data_collection 'APEX2 (Bruker, 2003)' _computing_data_reduction 'SAINT-Plus (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2000)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 110(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX2 CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 10368 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.28 _diffrn_standards_decay_% <1 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max .194 _exptl_crystal_size_mid .102 _exptl_crystal_size_min .083 _refine_diff_density_max 0.246 _refine_diff_density_min -0.188 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 141 _refine_ls_number_reflns 2342 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0387 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.3725P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0961 _refine_ls_wR_factor_ref 0.1076 _reflns_number_gt 1777 _reflns_number_total 2342 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ac6159.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2205199 _cod_database_fobs_code 2205199 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_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 O1 0.14055(5) 0.32400(18) 0.11429(8) 0.0212(2) Uani d . 1 O O2 0.12147(5) 0.63794(19) -0.00900(9) 0.0310(3) Uani d . 1 O C1 0.16329(7) 0.4983(2) 0.05057(11) 0.0194(3) Uani d . 1 C C2 0.24704(7) 0.4950(2) 0.06158(11) 0.0175(3) Uani d . 1 C C3 0.27718(7) 0.3287(2) -0.00623(11) 0.0183(3) Uani d . 1 C C4 0.35490(7) 0.3283(2) 0.00112(11) 0.0190(3) Uani d . 1 C C5 0.39856(7) 0.4937(2) 0.07480(11) 0.0195(3) Uani d . 1 C H5 0.4501 0.4939 0.0789 0.023 Uiso calc R 1 H C6 0.36865(7) 0.6584(2) 0.14242(11) 0.0183(3) Uani d . 1 C C7 0.29097(7) 0.6599(2) 0.13657(11) 0.0179(3) Uani d . 1 C C8 0.22805(8) 0.1537(3) -0.08612(12) 0.0234(3) Uani d . 1 C H8A 0.1765 0.1834 -0.0838 0.035 Uiso calc R 1 H H8B 0.2411 -0.0067 -0.0600 0.035 Uiso calc R 1 H H8C 0.2353 0.1732 -0.1654 0.035 Uiso calc R 1 H C9 0.39110(8) 0.1524(3) -0.06850(13) 0.0253(3) Uani d . 1 C H9A 0.4445 0.1743 -0.0503 0.038 Uiso calc R 1 H H9B 0.3727 0.1785 -0.1512 0.038 Uiso calc R 1 H H9C 0.3792 -0.0078 -0.0484 0.038 Uiso calc R 1 H C10 0.41932(8) 0.8323(3) 0.22051(12) 0.0239(3) Uani d . 1 C H10A 0.4703 0.8042 0.2142 0.036 Uiso calc R 1 H H10B 0.4145 0.8102 0.3008 0.036 Uiso calc R 1 H H10C 0.4054 0.9932 0.1962 0.036 Uiso calc R 1 H C11 0.25662(8) 0.8346(3) 0.20938(12) 0.0235(3) Uani d . 1 C H11A 0.2591 0.9933 0.1786 0.035 Uiso calc R 1 H H11B 0.2837 0.8296 0.2896 0.035 Uiso calc R 1 H H11C 0.2052 0.7922 0.2064 0.035 Uiso calc R 1 H C12 0.05964(7) 0.3028(3) 0.10351(13) 0.0249(3) Uani d . 1 C H12A 0.0353 0.2871 0.0212 0.030 Uiso calc R 1 H H12B 0.0401 0.4444 0.1353 0.030 Uiso calc R 1 H C13 0.04479(8) 0.0854(3) 0.17094(14) 0.0313(4) Uani d . 1 C H13A 0.0640 -0.0538 0.1385 0.047 Uiso calc R 1 H H13B -0.0082 0.0679 0.1654 0.047 Uiso calc R 1 H H13C 0.0691 0.1027 0.2522 0.047 Uiso calc R 1 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 O1 0.0161(5) 0.0226(6) 0.0245(5) 0.0006(4) 0.0027(4) 0.0045(4) O2 0.0221(5) 0.0285(6) 0.0401(6) 0.0045(4) 0.0010(4) 0.0136(5) C1 0.0218(7) 0.0178(7) 0.0180(7) 0.0002(6) 0.0024(5) -0.0014(6) C2 0.0187(6) 0.0163(7) 0.0169(6) 0.0012(5) 0.0019(5) 0.0047(5) C3 0.0232(7) 0.0156(7) 0.0155(6) -0.0003(5) 0.0024(5) 0.0039(5) C4 0.0250(7) 0.0154(7) 0.0175(6) 0.0016(6) 0.0062(5) 0.0042(5) C5 0.0176(6) 0.0197(8) 0.0213(7) 0.0003(5) 0.0045(5) 0.0058(6) C6 0.0217(7) 0.0149(7) 0.0172(6) -0.0013(5) 0.0018(5) 0.0048(5) C7 0.0217(7) 0.0148(7) 0.0168(6) 0.0023(5) 0.0029(5) 0.0031(5) C8 0.0263(7) 0.0216(8) 0.0217(7) -0.0016(6) 0.0038(6) -0.0030(6) C9 0.0298(8) 0.0218(8) 0.0266(7) 0.0019(6) 0.0110(6) 0.0000(6) C10 0.0250(7) 0.0222(8) 0.0235(7) -0.0042(6) 0.0028(6) -0.0003(6) C11 0.0279(7) 0.0189(8) 0.0236(7) 0.0031(6) 0.0048(6) -0.0012(6) C12 0.0165(7) 0.0281(9) 0.0300(8) 0.0012(6) 0.0047(5) 0.0018(6) C13 0.0231(7) 0.0321(9) 0.0388(9) -0.0029(7) 0.0064(6) 0.0048(7) 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' 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 _geom_angle_publ_flag C1 O1 C12 115.66(10) y O2 C1 O1 123.81(12) y O2 C1 C2 124.66(12) y O1 C1 C2 111.53(11) y C3 C2 C7 123.00(12) ? C3 C2 C1 117.88(12) ? C7 C2 C1 119.11(12) ? C2 C3 C4 118.32(12) ? C2 C3 C8 121.50(12) ? C4 C3 C8 120.17(12) ? C5 C4 C3 118.73(12) ? C5 C4 C9 120.21(12) ? C3 C4 C9 121.06(12) ? C6 C5 C4 122.96(12) ? C6 C5 H5 118.5 ? C4 C5 H5 118.5 ? C5 C6 C7 118.95(12) ? C5 C6 C10 120.13(12) ? C7 C6 C10 120.92(12) ? C2 C7 C6 118.04(12) ? C2 C7 C11 121.53(12) ? C6 C7 C11 120.43(12) ? C3 C8 H8A 109.5 ? C3 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? C3 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? C4 C9 H9A 109.5 ? C4 C9 H9B 109.5 ? H9A C9 H9B 109.5 ? C4 C9 H9C 109.5 ? H9A C9 H9C 109.5 ? H9B C9 H9C 109.5 ? C6 C10 H10A 109.5 ? C6 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? C6 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? C7 C11 H11A 109.5 ? C7 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? C7 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? O1 C12 C13 107.93(11) ? O1 C12 H12A 110.1 ? C13 C12 H12A 110.1 ? O1 C12 H12B 110.1 ? C13 C12 H12B 110.1 ? H12A C12 H12B 108.4 ? C12 C13 H13A 109.5 ? C12 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? C12 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.3369(16) y O1 C12 1.4591(15) y O2 C1 1.2048(16) y C1 C2 1.5055(18) y C2 C3 1.3986(19) y C2 C7 1.4001(18) y C3 C4 1.4015(18) y C3 C8 1.5087(18) y C4 C5 1.3921(19) y C4 C9 1.5056(19) y C5 C6 1.3894(19) y C5 H5 0.9300 ? C6 C7 1.4034(18) y C6 C10 1.5079(18) y C7 C11 1.5064(19) y C8 H8A 0.9600 ? C8 H8B 0.9600 ? C8 H8C 0.9600 ? C9 H9A 0.9600 ? C9 H9B 0.9600 ? C9 H9C 0.9600 ? C10 H10A 0.9600 ? C10 H10B 0.9600 ? C10 H10C 0.9600 ? C11 H11A 0.9600 ? C11 H11B 0.9600 ? C11 H11C 0.9600 ? C12 C13 1.498(2) y C12 H12A 0.9700 ? C12 H12B 0.9700 ? C13 H13A 0.9600 ? C13 H13B 0.9600 ? C13 H13C 0.9600 ? 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 C3 C2 C1 O1 79.95(15) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 310450 2 PubChem 349702