#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105037.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_2105037 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 'C10 H18 O4' _chemical_formula_sum 'C10 H18 O4' _chemical_formula_weight 202.24 _chemical_name_common 'Di-tert-butyl 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 118.35(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.120(2) _cell_length_b 10.650(2) _cell_length_c 11.277(2) _cell_measurement_reflns_used 2923 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.50 _cell_measurement_theta_min 2.10 _cell_volume 1175.3(5) _computing_cell_refinement 'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)' _computing_data_collection 'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150 _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Rigaku Mercury375R (2x2 bin mode)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 10287 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.42 _diffrn_reflns_theta_max 25.42 _diffrn_reflns_theta_min 2.81 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description block _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.350 _refine_diff_density_max 0.215 _refine_diff_density_min -0.204 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 2157 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0378 _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^)+(0.0496P)^2^+0.2312P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0962 _refine_ls_wR_factor_ref 0.0991 _reflns_number_gt 1947 _reflns_number_total 2157 _reflns_threshold_expression >2\s(i) _[local]_cod_data_source_file og5050.cif _[local]_cod_data_source_block DtBO150 _[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. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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 2105037 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 0.0358(5) 0.0270(5) 0.0350(5) 0.0016(4) 0.0084(4) 0.0019(4) O2 0.0286(5) 0.0247(4) 0.0258(4) -0.0017(3) 0.0052(4) -0.0019(3) O3 0.0327(5) 0.0353(5) 0.0463(6) 0.0065(4) 0.0055(5) -0.0115(4) O4 0.0233(4) 0.0278(5) 0.0339(5) -0.0002(3) 0.0056(4) -0.0047(4) C1 0.0240(6) 0.0287(6) 0.0255(6) 0.0005(5) 0.0111(5) 0.0004(5) C2 0.0255(6) 0.0287(6) 0.0241(6) 0.0013(5) 0.0090(5) -0.0002(5) C3 0.0272(6) 0.0277(6) 0.0274(6) -0.0063(5) 0.0088(5) -0.0064(5) C4 0.0354(7) 0.0396(8) 0.0355(7) -0.0066(6) 0.0178(6) -0.0106(6) C5 0.0338(7) 0.0407(8) 0.0409(8) -0.0102(6) 0.0196(7) -0.0086(6) C6 0.0394(8) 0.0377(8) 0.0339(7) -0.0020(7) 0.0012(7) -0.0046(6) C7 0.0252(6) 0.0314(7) 0.0316(7) -0.0051(5) 0.0067(5) -0.0072(5) C8 0.0288(7) 0.0385(8) 0.0639(11) -0.0023(7) 0.0018(8) -0.0015(8) C9 0.0449(9) 0.0744(12) 0.0341(8) -0.0206(9) 0.0168(7) -0.0195(8) C10 0.0405(8) 0.0343(7) 0.0492(9) -0.0063(7) 0.0184(7) -0.0031(6) 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 0.74774(9) 0.24501(8) -0.00265(9) 0.0360(3) Uani 1.000 O O2 0.89892(9) 0.11222(8) 0.15422(8) 0.0295(3) Uani 1.000 O O3 0.78947(10) -0.07157(9) -0.03240(10) 0.0435(3) Uani 1.000 O O4 0.59394(8) 0.04190(8) -0.12170(9) 0.0316(3) Uani 1.000 C C1 0.79158(12) 0.14207(11) 0.03922(12) 0.0263(3) Uani 1.000 C C2 0.72568(12) 0.02187(11) -0.04219(12) 0.0272(3) Uani 1.000 C C3 0.98620(12) 0.21197(11) 0.24990(12) 0.0291(3) Uani 1.000 C C4 0.90108(15) 0.29138(14) 0.29388(15) 0.0364(4) Uani 1.000 C C5 1.05216(15) 0.28863(15) 0.18294(15) 0.0377(4) Uani 1.000 C C6 1.09115(16) 0.13569(14) 0.36614(15) 0.0436(4) Uani 1.000 C C7 0.50436(13) -0.05755(12) -0.21575(13) 0.0322(4) Uani 1.000 C C8 0.36552(15) 0.00577(16) -0.2804(2) 0.0520(5) Uani 1.000 C C9 0.55381(18) -0.0880(2) -0.31620(16) 0.0519(6) Uani 1.000 C C10 0.50238(17) -0.17071(14) -0.13598(16) 0.0425(5) Uani 1.000 H H4A 0.9633(16) 0.3489(14) 0.3664(16) 0.040(4) Uiso 1.000 H H4B 0.8328(17) 0.3424(15) 0.2201(17) 0.044(4) Uiso 1.000 H H4C 0.8531(18) 0.2398(17) 0.3286(18) 0.056(5) Uiso 1.000 H H5A 1.1023(17) 0.2323(16) 0.1518(17) 0.053(5) Uiso 1.000 H H5B 1.1165(19) 0.3431(17) 0.2487(18) 0.056(5) Uiso 1.000 H H5C 0.9830(17) 0.3361(15) 0.1050(16) 0.042(4) Uiso 1.000 H H6A 1.0436(18) 0.0842(17) 0.4039(18) 0.056(5) Uiso 1.000 H H6B 1.1562(16) 0.1939(15) 0.4357(16) 0.042(4) Uiso 1.000 H H6C 1.1443(18) 0.0841(17) 0.3342(17) 0.054(5) Uiso 1.000 H H8A 0.2963(18) -0.0527(16) -0.3501(17) 0.050(4) Uiso 1.000 H H8B 0.334(3) 0.030(2) -0.210(3) 0.104(8) Uiso 1.000 H H8C 0.373(2) 0.072(2) -0.330(2) 0.065(6) Uiso 1.000 H H9A 0.486(2) -0.1446(17) -0.3845(19) 0.061(5) Uiso 1.000 H H9B 0.644(2) -0.1328(17) -0.2736(19) 0.065(6) Uiso 1.000 H H9C 0.559(2) -0.010(2) -0.361(2) 0.078(6) Uiso 1.000 H H10A 0.4318(19) -0.2320(18) -0.1991(19) 0.061(5) Uiso 1.000 H H10B 0.594(2) -0.2107(17) -0.0895(18) 0.060(5) Uiso 1.000 H H10C 0.474(2) -0.1426(18) -0.068(2) 0.068(6) 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 O2 C3 120.82(10) yes C2 O4 C7 121.14(10) yes O1 C1 O2 127.99(12) yes O1 C1 C2 122.27(12) yes O2 C1 C2 109.74(10) yes O3 C2 O4 127.90(12) yes O3 C2 C1 122.82(13) yes O4 C2 C1 109.27(11) yes O2 C3 C4 109.85(12) yes O2 C3 C5 108.93(11) yes O2 C3 C6 102.29(10) yes C4 C3 C5 112.76(12) no C4 C3 C6 111.13(12) no C5 C3 C6 111.35(14) no O4 C7 C8 102.08(11) yes O4 C7 C9 109.08(13) yes O4 C7 C10 109.63(11) yes C8 C7 C9 112.63(13) no C8 C7 C10 109.98(15) no C9 C7 C10 112.88(14) no C3 C4 H4A 108.3(11) no C3 C4 H4B 112.5(11) no C3 C4 H4C 111.4(12) no H4A C4 H4B 108.2(13) no H4A C4 H4C 108.6(15) no H4B C4 H4C 107.7(17) no C3 C5 H5A 109.7(11) no C3 C5 H5B 107.7(12) no C3 C5 H5C 111.2(12) no H5A C5 H5B 107.8(17) no H5A C5 H5C 109.0(15) no H5B C5 H5C 111.3(15) no C3 C6 H6A 108.7(12) no C3 C6 H6B 108.8(9) no C3 C6 H6C 109.3(10) no H6A C6 H6B 110.2(15) no H6A C6 H6C 112.5(16) no H6B C6 H6C 107.3(16) no C7 C8 H8A 109.0(11) no C7 C8 H8B 112.2(17) no C7 C8 H8C 105.4(15) no H8A C8 H8B 110(2) no H8A C8 H8C 104.6(16) no H8B C8 H8C 115.5(18) no C7 C9 H9A 107.5(14) no C7 C9 H9B 112.3(11) no C7 C9 H9C 109.5(13) no H9A C9 H9B 107.6(17) no H9A C9 H9C 108.9(16) no H9B C9 H9C 110.9(18) no C7 C10 H10A 108.8(11) no C7 C10 H10B 110.8(12) no C7 C10 H10C 108.4(11) no H10A C10 H10B 110.7(16) no H10A C10 H10C 108.1(18) no H10B C10 H10C 109.9(17) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.2016(15) yes O2 C1 1.3182(15) yes O2 C3 1.4967(15) yes O3 C2 1.1964(17) yes O4 C2 1.3221(17) yes O4 C7 1.4952(16) yes C1 C2 1.5426(17) no C3 C4 1.518(2) no C3 C5 1.517(2) no C3 C6 1.512(2) no C7 C8 1.517(2) no C7 C9 1.511(2) no C7 C10 1.510(2) no C4 H4A 0.993(16) no C4 H4B 0.982(17) no C4 H4C 0.97(2) no C5 H5A 0.990(19) no C5 H5B 0.946(19) no C5 H5C 0.989(17) no C6 H6A 0.99(2) no C6 H6B 0.992(17) no C6 H6C 0.99(2) no C8 H8A 1.012(18) no C8 H8B 1.04(3) no C8 H8C 0.93(2) no C9 H9A 0.987(19) no C9 H9B 1.00(2) no C9 H9C 0.99(2) no C10 H10A 1.01(2) no C10 H10B 0.99(2) no C10 H10C 1.00(2) 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 2.6881(14) . no O1 C4 2.9864(18) . no O1 C5 3.054(2) . no O2 O3 2.7035(14) . no O3 C9 3.029(2) . no O3 C10 3.022(2) . no O3 O2 2.7035(14) . no O4 O1 2.6881(14) . no O1 H8A 2.620(17) 2_654 no O1 H9A 2.57(2) 2_654 no O1 H4C 2.67(2) 4_554 no O1 H5C 2.499(19) . no O1 H4B 2.454(17) . no O3 H9B 2.502(19) . no O3 H10B 2.45(2) . no O3 H6B 2.677(16) 2_745 no O3 H5A 2.780(19) 3_755 no O3 H4A 2.625(18) 2_745 no O4 H10C 2.80(2) 3_655 no C1 C4 3.583(2) 4_554 no C4 C1 3.583(2) 4_555 no C4 O1 2.9864(18) . no C5 O1 3.054(2) . no C9 O3 3.029(2) . no C10 O3 3.022(2) . no C1 H4B 2.835(17) . no C1 H5C 2.802(18) . no C1 H4C 3.04(2) 4_554 no C2 H10B 2.797(19) . no C2 H9B 2.846(19) . no H4A H6B 2.52(3) . no H4A O3 2.625(18) 2_755 no H4B O1 2.454(17) . no H4B C1 2.835(17) . no H4B H5C 2.56(3) . no H4C H6A 2.50(3) . no H4C O1 2.67(2) 4_555 no H4C C1 3.04(2) 4_555 no H5A H6C 2.46(2) . no H5A O3 2.780(19) 3_755 no H5B H6B 2.51(2) . no H5C O1 2.499(19) . no H5C C1 2.802(18) . no H5C H4B 2.56(3) . no H6A H4C 2.50(3) . no H6B H4A 2.52(3) . no H6B H5B 2.51(2) . no H6B O3 2.677(16) 2_755 no H6C H5A 2.46(2) . no H8A H9A 2.52(3) . no H8A H10A 2.53(3) . no H8A O1 2.620(17) 2_644 no H8B H10C 2.45(3) . no H8C H9C 2.42(3) . no H8C H10B 2.58(3) 2_654 no H9A H8A 2.52(3) . no H9A O1 2.57(2) 2_644 no H9B O3 2.502(19) . no H9B C2 2.846(19) . no H9B H10B 2.53(3) . no H9C H8C 2.42(3) . no H10A H8A 2.53(3) . no H10B O3 2.45(2) . no H10B C2 2.797(19) . no H10B H9B 2.53(3) . no H10B H8C 2.58(3) 2_644 no H10C H8B 2.45(3) . no H10C O4 2.80(2) 3_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 C4 H4B O1 . 0.982(17) 2.454(17) 2.9864(18) 113.6(12) yes C5 H5C O1 . 0.989(17) 2.499(19) 3.054(2) 115.2(13) yes C9 H9A O1 2_644 0.987(19) 2.57(2) 3.475(2) 152.1(18) yes C9 H9B O3 . 1.00(2) 2.502(19) 3.029(2) 112.3(14) yes C10 H10B O3 . 0.99(2) 2.45(2) 3.022(2) 116.0(13) 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 C3 O2 C1 O1 -2.0(2) no C3 O2 C1 C2 176.94(11) no C1 O2 C3 C5 -63.71(16) no C1 O2 C3 C6 178.34(13) no C1 O2 C3 C4 60.25(15) no C2 O4 C7 C8 178.31(13) no C7 O4 C2 O3 -0.6(2) no C7 O4 C2 C1 178.20(11) no C2 O4 C7 C9 -62.32(16) no C2 O4 C7 C10 61.75(17) no O1 C1 C2 O3 150.41(15) no O2 C1 C2 O3 -28.57(19) no O2 C1 C2 O4 152.59(12) no O1 C1 C2 O4 -28.43(19) no _cod_database_fobs_code 2105037