#------------------------------------------------------------------------------ #$Date: 2015-02-25 13:01:53 +0000 (Wed, 25 Feb 2015) $ #$Revision: 132410 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105023.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_2105023 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_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' _chemical_name_systematic ? _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 105.525(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.734(4) _cell_length_b 4.3096(15) _cell_length_c 15.276(5) _cell_measurement_reflns_used 749 _cell_measurement_temperature 170 _cell_measurement_theta_max 47.55 _cell_measurement_theta_min 5.74 _cell_volume 744.3(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 170 _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 0.0703 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _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 6823 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.42 _diffrn_reflns_theta_max 25.42 _diffrn_reflns_theta_min 1.80 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.304 _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 0.175 _refine_diff_density_min -0.197 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 131 _refine_ls_number_reflns 1373 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.1098 _refine_ls_R_factor_gt 0.0508 _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^)+(0.0545P)^2^+0.0265P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1022 _refine_ls_wR_factor_ref 0.1281 _reflns_number_gt 757 _reflns_number_total 1373 _reflns_threshold_expression >2\s(i) _[local]_cod_data_source_file og5050.cif _[local]_cod_data_source_block DEO170 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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_database_code 2105023 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 0.0371(11) 0.0343(11) 0.0221(10) 0.0053(9) -0.0005(8) -0.0008(8) O2 0.0381(11) 0.0365(11) 0.0243(10) 0.0035(9) 0.0004(8) 0.0016(8) O3 0.0449(13) 0.0536(14) 0.0326(13) 0.0163(10) 0.0053(11) -0.0049(10) O4 0.0452(15) 0.0613(15) 0.0321(14) 0.0201(10) 0.0063(12) -0.0005(9) C1 0.061(2) 0.047(2) 0.031(2) 0.002(2) 0.0006(18) 0.0006(16) C2 0.043(2) 0.0369(19) 0.031(2) 0.0044(14) 0.0013(16) 0.0048(12) C3 0.0261(14) 0.0310(15) 0.0267(15) -0.0046(13) 0.0042(12) -0.0059(12) C4 0.0289(15) 0.0322(16) 0.0262(15) -0.0048(13) 0.0060(12) -0.0028(12) C5 0.037(2) 0.0342(19) 0.031(2) 0.0025(13) -0.0021(16) 0.0076(12) C6 0.065(3) 0.048(2) 0.0290(19) -0.002(2) -0.0012(17) 0.0042(16) 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 0.30851(15) 0.9188(4) 0.48954(10) 0.0328(6) Uani 1.000 O O2 0.19415(15) 1.0558(4) 0.25811(11) 0.0345(6) Uani 1.000 O O3 0.35192(17) 0.6924(5) 0.37013(13) 0.0447(8) Uani 1.000 O O4 0.13894(18) 1.2487(5) 0.37703(14) 0.0470(8) Uani 1.000 C C1 0.4056(4) 0.8231(9) 0.6464(2) 0.0486(12) Uani 1.000 C C2 0.3969(3) 0.7231(7) 0.5509(2) 0.0386(11) Uani 1.000 C C3 0.2963(2) 0.8712(6) 0.40207(16) 0.0285(8) Uani 1.000 C C4 0.1996(2) 1.0869(6) 0.34521(16) 0.0294(9) Uani 1.000 C C5 0.1054(3) 1.2512(7) 0.1964(2) 0.0362(11) Uani 1.000 C C6 0.1078(4) 1.1749(10) 0.1019(2) 0.0500(14) Uani 1.000 H H1A 0.466(3) 0.689(8) 0.686(2) 0.074(11) Uiso 1.000 H H1B 0.332(3) 0.785(7) 0.660(2) 0.056(11) Uiso 1.000 H H1C 0.434(3) 1.041(8) 0.660(2) 0.058(9) Uiso 1.000 H H2A 0.474(2) 0.754(6) 0.5347(18) 0.041(9) Uiso 1.000 H H2B 0.368(2) 0.508(7) 0.5350(18) 0.051(9) Uiso 1.000 H H5A 0.030(3) 1.203(7) 0.209(2) 0.074(12) Uiso 1.000 H H5B 0.129(3) 1.455(7) 0.214(2) 0.054(9) Uiso 1.000 H H6A 0.177(3) 1.235(8) 0.089(3) 0.093(16) Uiso 1.000 H H6B 0.091(3) 0.949(8) 0.0890(19) 0.066(10) Uiso 1.000 H H6C 0.043(3) 1.298(8) 0.059(2) 0.076(11) 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 115.1(2) yes C4 O2 C5 115.0(2) yes O1 C2 C1 108.0(3) yes O1 C3 O3 126.1(2) yes O1 C3 C4 109.9(2) yes O3 C3 C4 124.0(2) yes O2 C4 O4 126.7(2) yes O2 C4 C3 109.6(2) yes O4 C4 C3 123.6(2) yes O2 C5 C6 107.6(3) yes C2 C1 H1A 106.2(18) no C2 C1 H1B 109.4(18) no C2 C1 H1C 113.9(18) no H1A C1 H1B 108(3) no H1A C1 H1C 106(3) no H1B C1 H1C 113(3) no O1 C2 H2A 107.2(15) no O1 C2 H2B 104.1(15) no C1 C2 H2A 111.7(15) no C1 C2 H2B 115.8(16) no H2A C2 H2B 109(2) no O2 C5 H5A 106.0(18) no O2 C5 H5B 104(2) no C6 C5 H5A 113.4(18) no C6 C5 H5B 113.8(19) no H5A C5 H5B 111(3) no C5 C6 H6A 113(3) no C5 C6 H6B 110.6(17) no C5 C6 H6C 107.9(19) no H6A C6 H6B 112(3) no H6A C6 H6C 106(3) no H6B C6 H6C 108(3) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.465(4) yes O1 C3 1.321(3) yes O2 C4 1.322(3) yes O2 C5 1.469(4) yes O3 C3 1.195(3) yes O4 C4 1.189(3) yes C1 C2 1.498(4) no C3 C4 1.542(4) no C5 C6 1.488(4) no C1 H1A 0.99(3) no C1 H1B 0.96(4) no C1 H1C 1.00(3) no C2 H2A 1.01(2) no C2 H2B 1.00(3) no C5 H5A 0.98(4) no C5 H5B 0.94(3) no C6 H6A 0.92(4) no C6 H6B 1.00(3) no C6 H6C 1.01(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 2.665(3) . no O2 O3 2.667(3) . no O3 C4 3.128(3) 1_545 no O3 C2 3.383(4) 3_666 no O3 O2 2.667(3) . no O3 O4 3.171(3) 1_545 no O4 C3 3.221(4) 1_565 no O4 O1 2.665(3) . no O4 O3 3.171(3) 1_565 no O1 H6A 2.86(4) 4_575 no O1 H2B 2.68(3) 1_565 no O2 H1B 2.88(3) 4_564 no O2 H5B 2.73(3) 1_545 no O3 H2B 2.60(3) . no O3 H2A 2.90(3) 3_666 no O3 H1C 2.91(4) 3_676 no O3 H2A 2.55(3) . no O4 H5A 2.55(3) . no O4 H5B 2.62(3) . no O4 H5A 2.85(3) 2_555 no C2 O3 3.383(4) 3_666 no C3 O4 3.221(4) 1_545 no C3 C4 3.597(4) 1_545 no C4 C3 3.597(4) 1_565 no C4 O3 3.128(3) 1_565 no C1 H1A 3.04(3) 2_656 no C2 H2A 3.05(3) 3_666 no C3 H2A 3.07(3) 3_676 no C4 H5A 3.08(3) 2_545 no H1A C1 3.04(3) 2_646 no H1A H1C 2.42(4) 2_646 no H1B O2 2.88(3) 4_565 no H1C H1A 2.42(4) 2_656 no H1C O3 2.91(4) 3_676 no H2A O3 2.55(3) . no H2A O3 2.90(3) 3_666 no H2A C2 3.05(3) 3_666 no H2A C3 3.07(3) 3_676 no H2A H2A 2.58(4) 3_666 no H2A H2A 2.52(4) 3_676 no H2B O1 2.68(3) 1_545 no H2B O3 2.60(3) . no H5A O4 2.55(3) . no H5A O4 2.85(3) 2_545 no H5A C4 3.08(3) 2_555 no H5B O2 2.73(3) 1_565 no H5B O4 2.62(3) . no H6A O1 2.86(4) 4_574 no H6C H6C 2.52(5) 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 175.9(3) no C2 O1 C3 O3 -1.9(4) no C2 O1 C3 C4 179.1(2) no C5 O2 C4 O4 1.9(4) no C5 O2 C4 C3 -179.7(2) no C4 O2 C5 C6 -177.3(3) no O1 C3 C4 O2 175.1(2) no O1 C3 C4 O4 -6.4(4) no O3 C3 C4 O2 -3.9(4) no O3 C3 C4 O4 174.6(3) no _cod_database_fobs_code 2105023 _journal_paper_doi 10.1107/S0108768111037487