#------------------------------------------------------------------------------ #$Date: 2012-01-02 17:21:35 +0000 (Mon, 02 Jan 2012) $ #$Revision: 31763 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105026.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_2105026 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 'C4 H6 O4' _chemical_formula_sum 'C4 H6 O4' _chemical_formula_weight 118.09 _chemical_name_common 'Dimethyl oxalate' _chemical_name_systematic ; ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 104.31(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 3.851(2) _cell_length_b 11.840(6) _cell_length_c 6.227(3) _cell_measurement_reflns_used 508 _cell_measurement_temperature 200 _cell_measurement_theta_max 25.42 _cell_measurement_theta_min 3.44 _cell_volume 275.1(2) _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 200 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 4697 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.42 _diffrn_reflns_theta_max 25.42 _diffrn_reflns_theta_min 3.44 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description plate _exptl_crystal_F_000 124 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.170 _refine_diff_density_max 0.208 _refine_diff_density_min -0.225 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 49 _refine_ls_number_reflns 508 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0557 _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^)+(0.0792P)^2^+0.1169P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1450 _refine_ls_wR_factor_ref 0.1533 _reflns_number_gt 390 _reflns_number_total 508 _reflns_threshold_expression >2\s(i) _[local]_cod_data_source_file og5050.cif _[local]_cod_data_source_block DMO200 _[local]_cod_cif_authors_sg_H-M 'P 21/n' _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 2105026 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+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 0.0696(16) 0.0505(12) 0.0416(11) -0.0140(9) 0.0180(11) -0.0006(8) O2 0.0480(12) 0.0500(12) 0.0303(10) -0.0039(8) 0.0090(8) -0.0019(7) C1 0.0383(14) 0.0400(14) 0.0329(13) 0.0055(10) 0.0072(11) 0.0032(10) C2 0.0506(19) 0.0580(19) 0.0415(16) -0.0051(14) 0.0093(14) -0.0093(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 0.2569(5) 0.11916(15) 0.4753(3) 0.0532(8) Uani 1.000 O O2 0.0908(5) 0.04940(14) 0.7725(3) 0.0429(7) Uani 1.000 C C1 0.1044(7) 0.05054(19) 0.5606(4) 0.0374(8) Uani 1.000 C C2 0.2765(8) 0.1420(3) 0.9076(5) 0.0504(10) Uani 1.000 H H1 0.236(10) 0.129(3) 1.058(7) 0.075(11) Uiso 1.000 H H2 0.171(9) 0.216(3) 0.847(5) 0.063(9) Uiso 1.000 H H3 0.532(9) 0.140(2) 0.908(5) 0.062(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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O2 C2 . 115.5(2) yes O1 C1 O2 . 126.0(2) yes O1 C1 C1 3_556 124.4(2) yes O2 C1 C1 3_556 109.6(2) yes O2 C2 H1 . 105(2) no O2 C2 H2 . 110.2(19) no O2 C2 H3 . 109.3(15) no H1 C2 H2 . 110(3) no H1 C2 H3 . 113(3) no H2 C2 H3 . 110(3) no 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 C1 . 1.201(3) yes O2 C1 . 1.334(3) yes O2 C2 . 1.457(4) yes C1 C1 3_556 1.533(3) no C2 H1 . 1.00(4) no C2 H2 . 1.00(3) no C2 H3 . 0.98(4) 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 C1 3.277(4) 1_655 no O1 O2 2.671(3) 3_556 no O1 C1 3.226(4) 3_656 no O1 C2 3.348(4) 4_454 no O2 O1 2.671(3) 3_556 no O1 H1 2.58(4) 1_554 no O1 H3 2.65(3) . no O1 H2 2.76(4) 4_554 no O1 H2 2.68(3) . no O2 H3 2.72(3) 1_455 no O2 H1 2.80(4) 3_557 no C1 O1 3.277(4) 1_455 no C1 O1 3.226(4) 3_656 no C1 C1 3.525(4) 3_656 no C2 O1 3.348(4) 4_555 no C2 H3 2.87(4) 1_455 no H1 O1 2.58(4) 1_556 no H1 O2 2.80(4) 3_557 no H2 O1 2.68(3) . no H2 O1 2.76(4) 4_455 no H3 O1 2.65(3) . no H3 O2 2.72(3) 1_655 no H3 C2 2.87(4) 1_655 no 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 _geom_hbond_publ_flag C2 H1 O1 1_556 1.00(4) 2.58(4) 3.565(4) 168(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_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 O2 C1 O1 . . 0.9(4) no C2 O2 C1 C1 . 3_556 -179.4(2) no O1 C1 C1 O1 3_556 3_556 180.0(3) no O1 C1 C1 O2 3_556 3_556 -0.3(4) no O2 C1 C1 O1 3_556 3_556 0.3(4) no O2 C1 C1 O2 3_556 3_556 -180.0(2) no