#------------------------------------------------------------------------------ #$Date: 2015-02-25 13:01:53 +0000 (Wed, 25 Feb 2015) $ #$Revision: 132410 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105031.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_2105031 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-n-butyl oxalate' _chemical_name_systematic ? _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 95.896(12) _cell_angle_beta 97.964(12) _cell_angle_gamma 96.656(13) _cell_formula_units_Z 1 _cell_length_a 4.593(4) _cell_length_b 4.702(4) _cell_length_c 14.030(11) _cell_measurement_reflns_used 1094 _cell_measurement_temperature 210 _cell_measurement_theta_max 56.425 _cell_measurement_theta_min 5.907 _cell_volume 295.9(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 210 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _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 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2968 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 26.35 _diffrn_reflns_theta_max 26.35 _diffrn_reflns_theta_min 1.48 _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 '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.135 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description cylindrical _exptl_crystal_F_000 110 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.350 _refine_diff_density_max 0.864 _refine_diff_density_min -0.337 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 1197 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.094 _refine_ls_R_factor_all 0.1431 _refine_ls_R_factor_gt 0.1148 _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^)+(0.1477P)^2^+0.5941P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2986 _refine_ls_wR_factor_ref 0.3195 _reflns_number_gt 898 _reflns_number_total 1197 _reflns_threshold_expression >2\s(i) _[local]_cod_data_source_file og5050.cif _[local]_cod_data_source_block DnBO210 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 2105031 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-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 0.0467(18) 0.0433(18) 0.0421(18) 0.0265(14) 0.0107(13) 0.0004(13) O2 0.0418(17) 0.0423(17) 0.0380(17) 0.0260(13) 0.0114(12) 0.0114(12) C1 0.0272(19) 0.0242(18) 0.038(2) 0.0075(15) 0.0092(15) 0.0049(15) C2 0.050(3) 0.056(3) 0.048(3) 0.033(3) 0.007(2) 0.016(2) C3 0.094(5) 0.094(5) 0.062(4) 0.065(4) 0.025(3) 0.035(3) C4 0.117(6) 0.090(5) 0.057(4) 0.056(4) 0.015(4) 0.021(3) C5 0.127(7) 0.143(7) 0.060(4) 0.064(6) 0.037(4) 0.044(4) 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy O O1 0.2744(7) 0.2455(7) 0.0435(2) 0.0424(10) Uani . . 1.000 O O2 0.3295(6) 0.0887(6) -0.1096(2) 0.0381(10) Uani . . 1.000 C C1 0.3835(8) 0.1004(8) -0.0150(3) 0.0290(11) Uani . . 1.000 C C2 0.1077(12) 0.2648(13) -0.1494(4) 0.0486(17) Uani . . 1.000 C C3 0.1898(16) 0.3694(16) -0.2379(4) 0.076(3) Uani . . 1.000 C C4 0.2328(19) 0.1651(16) -0.3185(4) 0.084(3) Uani . . 1.000 C C5 0.310(2) 0.295(2) -0.4069(5) 0.102(4) Uani . . 1.000 H H2A 0.126(16) 0.395(16) -0.102(5) 0.09(2) Uiso . . 1.000 H H2B -0.086(16) 0.137(14) -0.165(4) 0.076(19) Uiso . . 1.000 H H3A 0.03650 0.48320 -0.26250 0.0910 Uiso calc R 1.000 H H3B 0.37430 0.50250 -0.21920 0.0910 Uiso calc R 1.000 H H4A 0.05060 0.02910 -0.33760 0.1000 Uiso calc R 1.000 H H4B 0.39120 0.05440 -0.29560 0.1000 Uiso calc R 1.000 H H5A 0.15400 0.40260 -0.43120 0.1530 Uiso calc R 1.000 H H5B 0.33100 0.14200 -0.45650 0.1530 Uiso calc R 1.000 H H5C 0.49570 0.42300 -0.38990 0.1530 Uiso calc R 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 . 116.8(3) yes O1 C1 O2 . 126.9(4) yes O1 C1 C1 2_655 122.8(4) yes O2 C1 C1 2_655 110.4(3) yes O2 C2 C3 . 109.7(5) yes C2 C3 C4 . 120.0(6) no C3 C4 C5 . 115.7(7) no O2 C2 H2A . 99(5) no O2 C2 H2B . 107(4) no C3 C2 H2A . 114(5) no C3 C2 H2B . 110(3) no H2A C2 H2B . 117(6) no C2 C3 H3A . 107.00 no C2 C3 H3B . 107.00 no C4 C3 H3A . 107.00 no C4 C3 H3B . 107.00 no H3A C3 H3B . 107.00 no C3 C4 H4A . 108.00 no C3 C4 H4B . 108.00 no C5 C4 H4A . 108.00 no C5 C4 H4B . 108.00 no H4A C4 H4B . 107.00 no C4 C5 H5A . 110.00 no C4 C5 H5B . 109.00 no C4 C5 H5C . 109.00 no H5A C5 H5B . 110.00 no H5A C5 H5C . 110.00 no H5B C5 H5C . 109.00 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 . 1.212(5) yes O2 C1 . 1.310(5) yes O2 C2 . 1.473(7) yes C1 C1 2_655 1.551(6) no C2 C3 . 1.462(8) no C3 C4 . 1.457(9) no C4 C5 . 1.505(10) no C2 H2A . 0.84(7) no C2 H2B . 1.00(7) no C3 H3A . 0.9800 no C3 H3B . 0.9800 no C4 H4A . 0.9800 no C4 H4B . 0.9800 no C5 H5A . 0.9700 no C5 H5B . 0.9700 no C5 H5C . 0.9700 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 3.214(6) 2_555 no O1 O1 3.224(5) 2_555 no O1 O2 2.671(5) 2_655 no O1 C2 3.398(7) 2_565 no O1 C1 3.376(6) 2_665 no O1 C2 3.395(7) 2_555 no O2 O1 2.671(5) 2_655 no O1 H2A 2.79(7) 2_565 no O1 H2B 2.75(6) 2_555 no O1 H2A 2.27(7) . no O1 H3B 2.8200 2_665 no O2 H2B 2.89(7) 1_655 no O2 H4B 2.6500 . no C1 O1 3.214(6) 2_555 no C1 O1 3.376(6) 2_665 no C2 O1 3.395(7) 2_555 no C2 O1 3.398(7) 2_565 no H2A O1 2.27(7) . no H2A O1 2.79(7) 2_565 no H2B O2 2.89(7) 1_455 no H2B H4A 2.6000 . no H2B O1 2.75(6) 2_555 no H3A H5A 2.5000 . no H3B H5C 2.5300 . no H3B O1 2.8200 2_665 no H4A H2B 2.6000 . no H4B O2 2.6500 . no H5A H3A 2.5000 . no H5A H5A 2.5400 2_564 no H5B H5B 2.5200 2_654 no H5C H3B 2.5300 . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C2 H2A O1 0.84(7) 2.27(7) 2.722(7) 114(6) 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 . . -1.6(6) no C2 O2 C1 C1 . 2_655 179.0(4) no C1 O2 C2 C3 . . 146.3(4) no O1 C1 C1 O1 2_655 2_655 180.0(4) no O2 C1 C1 O1 2_655 2_655 -0.5(5) no O2 C1 C1 O2 2_655 2_655 -180.0(3) no O1 C1 C1 O2 2_655 2_655 0.5(5) no O2 C2 C3 C4 . . 56.6(8) no C2 C3 C4 C5 . . 178.7(7) no _cod_database_fobs_code 2105031 _journal_paper_doi 10.1107/S0108768111037487