#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105022.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_2105022 loop_ _publ_author_name 'Joseph, Sumy' 'Sathishkumar, Ranganathan' 'Mahapatra, Sudarshan' 'Desiraju, Gautam R.' _publ_section_title ; Crystal packing and melting temperatures of small oxalate esters: the role of C---H···O hydrogen bonding ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 525 _journal_page_last 534 _journal_paper_doi 10.1107/S0108768111037487 _journal_volume 67 _journal_year 2011 _chemical_formula_moiety 'C6 H10 O4' _chemical_formula_sum 'C6 H10 O4' _chemical_formula_weight 146.14 _chemical_name_common 'Diethyl oxalate' _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 _cell_angle_alpha 90 _cell_angle_beta 104.938(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.581(4) _cell_length_b 4.2812(15) _cell_length_c 15.282(5) _cell_measurement_reflns_used 894 _cell_measurement_temperature 90 _cell_measurement_theta_max 47.55 _cell_measurement_theta_min 5.78 _cell_volume 732.1(4) _computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _diffrn_ambient_temperature 90 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 6617 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.41 _diffrn_reflns_theta_max 25.41 _diffrn_reflns_theta_min 1.82 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description block _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.350 _refine_diff_density_max 0.211 _refine_diff_density_min -0.185 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 131 _refine_ls_number_reflns 1345 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0494 _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^)+(0.0552P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1005 _refine_ls_wR_factor_ref 0.1210 _reflns_number_gt 817 _reflns_number_total 1345 _reflns_threshold_expression >2\s(i) _cod_data_source_file og5050.cif _cod_data_source_block DEO90 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2105022 _cod_database_fobs_code 2105022 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z 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 0.0201(10) 0.0165(10) 0.0139(10) 0.0038(7) -0.0006(7) 0.0007(7) O2 0.0195(10) 0.0179(10) 0.0138(9) 0.0013(7) -0.0015(7) 0.0002(7) O3 0.0252(11) 0.0269(11) 0.0209(13) 0.0088(9) 0.0024(10) -0.0023(9) O4 0.0225(12) 0.0316(12) 0.0193(13) 0.0099(8) 0.0017(10) -0.0007(8) C1 0.0313(18) 0.0249(16) 0.0178(17) 0.0049(15) -0.0013(14) 0.0023(13) C2 0.0220(17) 0.0168(15) 0.0173(18) 0.0025(11) -0.0025(13) 0.0045(10) C3 0.0133(13) 0.0162(14) 0.0175(14) -0.0038(11) 0.0026(11) -0.0028(11) C4 0.0159(13) 0.0163(14) 0.0156(14) -0.0041(11) 0.0013(11) -0.0015(11) C5 0.0194(17) 0.0148(15) 0.025(2) 0.0022(11) -0.0003(14) 0.0046(11) C6 0.0342(19) 0.0218(16) 0.0191(17) -0.0042(15) -0.0007(14) 0.0012(13) 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_thermal_displace_type _atom_site_occupancy O O1 0.30789(14) 0.9206(4) 0.48973(10) 0.0178(6) Uani 1.000 O O2 0.19468(14) 1.0568(4) 0.25823(11) 0.0181(6) Uani 1.000 O O3 0.35363(16) 0.6918(4) 0.36993(13) 0.0250(7) Uani 1.000 O O4 0.13725(16) 1.2547(4) 0.37700(13) 0.0252(7) Uani 1.000 C C1 0.4042(3) 0.8256(8) 0.6463(2) 0.0261(10) Uani 1.000 C C2 0.3976(3) 0.7243(6) 0.5515(2) 0.0201(10) Uani 1.000 C C3 0.2966(2) 0.8724(6) 0.40214(16) 0.0159(8) Uani 1.000 C C4 0.1994(2) 1.0889(6) 0.34525(16) 0.0164(8) Uani 1.000 C C5 0.1057(3) 1.2529(6) 0.1966(2) 0.0208(10) Uani 1.000 C C6 0.1078(3) 1.1725(8) 0.1014(2) 0.0264(10) Uani 1.000 H H1A 0.462(2) 0.693(6) 0.6857(19) 0.028(8) Uiso 1.000 H H1B 0.325(3) 0.794(6) 0.6629(19) 0.024(8) Uiso 1.000 H H1C 0.431(2) 1.056(7) 0.6574(18) 0.034(8) Uiso 1.000 H H2A 0.476(2) 0.751(5) 0.5343(17) 0.018(8) Uiso 1.000 H H2B 0.367(2) 0.505(7) 0.5349(17) 0.030(8) Uiso 1.000 H H5A 0.028(3) 1.211(6) 0.208(2) 0.032(9) Uiso 1.000 H H5B 0.124(2) 1.461(6) 0.2114(17) 0.019(7) Uiso 1.000 H H6A 0.181(3) 1.228(7) 0.091(2) 0.041(10) Uiso 1.000 H H6B 0.086(2) 0.950(7) 0.0867(16) 0.027(7) Uiso 1.000 H H6C 0.041(3) 1.300(7) 0.057(2) 0.039(9) Uiso 1.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 '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 C2 O1 C3 115.3(2) yes C4 O2 C5 115.2(2) yes O1 C2 C1 107.9(2) yes O1 C3 O3 126.3(2) yes O1 C3 C4 110.1(2) yes O3 C3 C4 123.7(2) yes O2 C4 O4 126.5(2) yes O2 C4 C3 109.8(2) yes O4 C4 C3 123.7(2) yes O2 C5 C6 107.9(2) yes C2 C1 H1A 106.8(16) no C2 C1 H1B 112.2(16) no C2 C1 H1C 111.9(15) no H1A C1 H1B 107(2) no H1A C1 H1C 109(2) no H1B C1 H1C 110(2) no O1 C2 H2A 107.5(14) no O1 C2 H2B 103.0(15) no C1 C2 H2A 113.1(14) no C1 C2 H2B 116.0(15) no H2A C2 H2B 108.6(19) no O2 C5 H5A 107.9(17) no O2 C5 H5B 108.3(15) no C6 C5 H5A 112.1(17) no C6 C5 H5B 113.3(16) no H5A C5 H5B 107(2) no C5 C6 H6A 110.4(19) no C5 C6 H6B 111.8(14) no C5 C6 H6C 108.4(18) no H6A C6 H6B 113(2) no H6A C6 H6C 108(3) no H6B C6 H6C 105(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.474(3) yes O1 C3 1.327(3) yes O2 C4 1.324(3) yes O2 C5 1.467(3) yes O3 C3 1.202(3) yes O4 C4 1.199(3) yes C1 C2 1.495(4) no C3 C4 1.542(4) no C5 C6 1.501(4) no C1 H1A 0.96(3) no C1 H1B 1.02(4) no C1 H1C 1.04(3) no C2 H2A 1.02(2) no C2 H2B 1.01(3) no C5 H5A 0.98(4) no C5 H5B 0.93(3) no C6 H6A 0.93(4) no C6 H6B 1.00(3) no C6 H6C 1.04(3) 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 O1 O4 2.677(3) . no O2 O3 2.669(3) . no O3 C4 3.106(3) 1_545 no O3 C2 3.337(4) 3_666 no O3 O2 2.669(3) . no O3 O4 3.152(3) 1_545 no O4 C3 3.191(3) 1_565 no O4 O1 2.677(3) . no O4 O3 3.152(3) 1_565 no O1 H6A 2.83(3) 4_575 no O1 H2B 2.64(3) 1_565 no O2 H1B 2.79(3) 4_564 no O2 H5B 2.72(3) 1_545 no O3 H2B 2.61(3) . no O3 H2A 2.85(2) 3_666 no O3 H1C 2.85(3) 3_676 no O3 H2A 2.56(3) . no O4 H5A 2.57(3) . no O4 H5B 2.65(3) . no O4 H5A 2.81(3) 2_555 no O4 H6B 2.90(2) 2_555 no C2 O3 3.337(4) 3_666 no C3 O4 3.191(3) 1_545 no C3 C4 3.574(4) 1_545 no C4 C3 3.574(4) 1_565 no C4 O3 3.106(3) 1_565 no C1 H1A 3.07(3) 2_656 no C2 H2A 3.00(2) 3_666 no C3 H2A 3.03(2) 3_676 no C4 H5A 3.02(3) 2_545 no C5 H5A 3.09(3) 2_555 no H1A C1 3.07(3) 2_646 no H1A H1C 2.47(4) 2_646 no H1B O2 2.79(3) 4_565 no H1C H1A 2.47(4) 2_656 no H1C O3 2.85(3) 3_676 no H2A O3 2.56(3) . no H2A O3 2.85(2) 3_666 no H2A C2 3.00(2) 3_666 no H2A C3 3.03(2) 3_676 no H2A H2A 2.52(3) 3_666 no H2A H2A 2.50(3) 3_676 no H2A H2B 2.57(3) 3_666 no H2B O1 2.64(3) 1_545 no H2B O3 2.61(3) . no H2B H2A 2.57(3) 3_666 no H5A O4 2.57(3) . no H5A O4 2.81(3) 2_545 no H5A C4 3.02(3) 2_555 no H5A C5 3.09(3) 2_545 no H5B O2 2.72(3) 1_565 no H5B O4 2.65(3) . no H6A O1 2.83(3) 4_574 no H6B O4 2.90(2) 2_545 no H6B H6C 2.54(4) 3_575 no H6C H6B 2.54(4) 3_575 no H6C H6C 2.45(4) 3_585 no 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 O1 C2 C1 176.0(2) no C2 O1 C3 O3 -1.7(4) no C2 O1 C3 C4 179.4(2) no C5 O2 C4 O4 1.7(4) no C5 O2 C4 C3 -179.6(2) no C4 O2 C5 C6 -176.7(2) no O1 C3 C4 O2 175.4(2) no O1 C3 C4 O4 -5.9(3) no O3 C3 C4 O2 -3.7(3) no O3 C3 C4 O4 175.1(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 6998 2 PubChem 7268