#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105040.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_2105040 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 'C5 H8 O4' _chemical_formula_sum 'C5 H8 O4' _chemical_formula_weight 132.11 _chemical_name_common 'Methy lethyl 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 95.092(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.321(8) _cell_length_b 4.425(2) _cell_length_c 9.127(4) _cell_measurement_reflns_used 1965 _cell_measurement_temperature 90 _cell_measurement_theta_max 55.39 _cell_measurement_theta_min 5.01 _cell_volume 656.6(5) _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 0.991 _diffrn_measured_fraction_theta_max 0.991 _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 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5453 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.41 _diffrn_reflns_theta_max 25.41 _diffrn_reflns_theta_min 2.51 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description cylindrical _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.350 _refine_diff_density_max 0.489 _refine_diff_density_min -0.450 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.299 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 114 _refine_ls_number_reflns 1207 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.299 _refine_ls_R_factor_all 0.1208 _refine_ls_R_factor_gt 0.0930 _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^)+(0.1139P)^2^+1.8164P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2596 _refine_ls_wR_factor_ref 0.2795 _reflns_number_gt 918 _reflns_number_total 1207 _reflns_threshold_expression >2\s(i) _cod_data_source_file og5050.cif _cod_data_source_block MEO90 _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 2105040 _cod_database_fobs_code 2105040 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 0.0247(19) 0.0137(17) 0.0204(17) 0.0008(13) 0.0001(13) 0.0014(13) O2 0.0246(18) 0.0130(18) 0.0241(17) 0.0049(14) -0.0013(14) 0.0005(14) O3 0.0240(18) 0.0161(19) 0.0235(17) 0.0001(14) -0.0006(14) 0.0038(14) O4 0.0199(18) 0.0179(19) 0.0258(18) 0.0026(14) 0.0016(13) 0.0025(14) C1 0.025(3) 0.020(3) 0.024(3) 0.001(2) 0.002(2) -0.002(2) C2 0.021(2) 0.012(2) 0.018(2) 0.0033(19) 0.0000(18) -0.0054(19) C3 0.025(3) 0.012(2) 0.018(2) 0.003(2) -0.0032(19) -0.0095(19) C4 0.034(3) 0.022(3) 0.028(3) -0.001(2) 0.005(2) 0.010(2) C5 0.033(3) 0.062(5) 0.089(6) 0.008(4) 0.022(4) 0.045(5) 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 0.0949(2) 0.3973(8) 0.5517(4) 0.0197(10) Uani 1.000 O O2 0.2200(2) 0.2146(8) 0.6321(4) 0.0208(10) Uani 1.000 O O3 0.1636(2) 0.7827(8) 0.3760(4) 0.0214(10) Uani 1.000 O O4 0.2882(2) 0.5957(8) 0.4523(4) 0.0212(11) Uani 1.000 C C1 0.0569(3) 0.1949(13) 0.6497(6) 0.0230(17) Uani 1.000 C C2 0.1759(3) 0.3794(11) 0.5571(5) 0.0171(12) Uani 1.000 C C3 0.2079(3) 0.6147(11) 0.4492(5) 0.0186(14) Uani 1.000 C C4 0.3257(4) 0.8025(14) 0.3519(6) 0.0279(17) Uani 1.000 C C5 0.4159(4) 0.743(2) 0.3714(12) 0.060(3) Uani 1.000 H H1A -0.004(3) 0.228(12) 0.640(5) 0.015(12) Uiso 1.000 H H1B 0.081(4) 0.002(16) 0.624(7) 0.035(16) Uiso 1.000 H H1C 0.075(3) 0.262(13) 0.745(6) 0.023(14) Uiso 1.000 H H4A 0.305(4) 0.780(19) 0.244(8) 0.06(2) Uiso 1.000 H H4B 0.319(4) 0.996(17) 0.380(7) 0.038(18) Uiso 1.000 H H5A 0.432(7) 0.81(3) 0.491(14) 0.12(4) Uiso 1.000 H H5B 0.437(4) 0.845(18) 0.287(9) 0.06(2) Uiso 1.000 H H5C 0.436(5) 0.536(19) 0.350(8) 0.05(2) 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 C1 O1 C2 115.0(4) yes C3 O4 C4 114.7(4) yes O1 C2 O2 127.4(5) yes O1 C2 C3 109.1(4) yes O2 C2 C3 123.5(4) yes O3 C3 O4 127.2(5) yes O3 C3 C2 123.3(4) yes O4 C3 C2 109.6(4) yes O4 C4 C5 106.1(5) yes O1 C1 H1A 109(3) no O1 C1 H1B 101(4) no O1 C1 H1C 105(3) no H1A C1 H1B 122(5) no H1A C1 H1C 105(4) no H1B C1 H1C 113(5) no O4 C4 H4A 115(4) no O4 C4 H4B 110(4) no C5 C4 H4A 110(4) no C5 C4 H4B 106(4) no H4A C4 H4B 109(6) no C4 C5 H5A 102(6) no C4 C5 H5B 104(4) no C4 C5 H5C 119(5) no H5A C5 H5B 124(8) no H5A C5 H5C 112(8) no H5B C5 H5C 97(6) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.444(7) yes O1 C2 1.321(6) yes O2 C2 1.196(6) yes O3 C3 1.198(6) yes O4 C3 1.311(6) yes O4 C4 1.467(7) yes C2 C3 1.555(7) no C4 C5 1.491(9) no C1 H1A 1.00(5) no C1 H1B 0.98(7) no C1 H1C 0.94(6) no C4 H4A 1.02(7) no C4 H4B 0.90(7) no C5 H5A 1.14(13) no C5 H5B 0.98(8) no C5 H5C 1.00(8) 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 O3 2.656(5) . no O2 O3 3.095(5) 1_545 no O2 C3 3.262(6) 4_555 no O2 C4 3.409(7) 4_555 no O2 O4 2.665(5) . no O2 C3 3.133(6) 1_545 no O2 C4 3.309(7) 4_565 no O3 C2 3.112(6) 1_565 no O3 C2 3.294(6) 4_564 no O3 C1 3.336(7) 4_554 no O3 O2 3.095(5) 1_565 no O3 O1 2.656(5) . no O4 O2 2.665(5) . no O1 H1C 2.88(5) 4_554 no O1 H1B 2.77(7) 1_565 no O1 H1A 2.75(5) 3_566 no O2 H4A 2.78(8) 4_565 no O2 H4A 2.74(8) 4_555 no O2 H1B 2.45(7) . no O2 H1C 2.67(5) . no O3 H1B 2.90(7) 1_565 no O3 H1A 2.60(5) 3_566 no O3 H4B 2.70(7) . no O3 H1B 2.85(6) 4_554 no O3 H1C 2.70(5) 4_564 no O3 H4A 2.70(7) . no O4 H4B 2.79(7) 1_545 no O4 H4A 2.71(7) 4_565 no C1 C1 3.507(8) 2_546 no C1 C1 3.507(8) 2_556 no C1 O3 3.336(7) 4_555 no C2 O3 3.112(6) 1_545 no C2 C3 3.576(7) 1_545 no C2 O3 3.294(6) 4_565 no C3 O2 3.133(6) 1_565 no C3 C2 3.576(7) 1_565 no C3 O2 3.262(6) 4_554 no C4 O2 3.409(7) 4_554 no C4 O2 3.309(7) 4_564 no C1 H1A 3.00(5) 2_546 no C1 H1C 3.10(5) 2_546 no C2 H4A 3.00(7) 4_565 no C3 H4A 3.04(7) 4_565 no H1A C1 3.00(5) 2_556 no H1A O1 2.75(5) 3_566 no H1A O3 2.60(5) 3_566 no H1B O1 2.77(7) 1_545 no H1B O2 2.45(7) . no H1B O3 2.90(7) 1_545 no H1B O3 2.85(7) 4_555 no H1C O2 2.67(5) . no H1C C1 3.10(5) 2_556 no H1C O1 2.88(5) 4_555 no H1C O3 2.70(5) 4_565 no H4A O3 2.70(7) . no H4A O2 2.74(8) 4_554 no H4A O2 2.78(8) 4_564 no H4A O4 2.71(7) 4_564 no H4A C2 3.00(7) 4_564 no H4A C3 3.04(7) 4_564 no H4B O3 2.70(7) . no H4B O4 2.79(7) 1_565 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 C1 H1A O3 3_566 1.00(5) 2.60(5) 3.587(6) 170(4) 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 _geom_torsion_publ_flag C1 O1 C2 O2 0.7(7) no C1 O1 C2 C3 -178.6(4) no C3 O4 C4 C5 -179.5(5) no C4 O4 C3 O3 -1.1(7) no C4 O4 C3 C2 178.6(4) no O1 C2 C3 O3 0.6(6) no O1 C2 C3 O4 -179.1(4) no O2 C2 C3 O3 -178.8(5) no O2 C2 C3 O4 1.5(7) no