#------------------------------------------------------------------------------ #$Date: 2012-01-02 17:21:35 +0000 (Mon, 02 Jan 2012) $ #$Revision: 31763 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105029.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_2105029 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 'C8 H14 O4' _chemical_formula_sum 'C8 H14 O4' _chemical_formula_weight 174.19 _chemical_name_common 'Diisopropyl 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 92.483(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.3575(12) _cell_length_b 9.949(3) _cell_length_c 11.384(3) _cell_measurement_reflns_used 1370 _cell_measurement_temperature 210 _cell_measurement_theta_max 48.18 _cell_measurement_theta_min 5.44 _cell_volume 493.1(2) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _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 4599 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.41 _diffrn_reflns_theta_max 25.41 _diffrn_reflns_theta_min 2.72 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description block _exptl_crystal_F_000 188 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.350 _refine_diff_density_max 0.177 _refine_diff_density_min -0.131 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 83 _refine_ls_number_reflns 909 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0395 _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^)+(0.0396P)^2^+0.1310P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.1006 _reflns_number_gt 676 _reflns_number_total 909 _reflns_threshold_expression >2\s(i) _[local]_cod_data_source_file og5050.cif _[local]_cod_data_source_block DiPO210 _[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 2105029 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 0.0515(8) 0.0400(7) 0.0541(8) -0.0039(6) -0.0177(6) -0.0009(6) O2 0.0412(7) 0.0332(7) 0.0395(7) 0.0002(5) -0.0049(5) 0.0068(5) C1 0.0329(9) 0.0313(9) 0.0319(9) 0.0009(8) 0.0038(7) 0.0000(7) C2 0.0428(11) 0.0410(11) 0.0421(11) 0.0037(9) -0.0063(8) 0.0102(8) C3 0.119(3) 0.0514(15) 0.0710(19) 0.0351(17) -0.0243(19) 0.0030(12) C4 0.0704(17) 0.0681(16) 0.0445(12) 0.0078(14) -0.0013(11) 0.0166(11) 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 0.2924(3) 0.54776(12) 0.10101(11) 0.0491(4) Uani 1.000 O O2 0.0904(3) 0.34389(12) 0.06104(10) 0.0382(4) Uani 1.000 C C1 0.1168(4) 0.47524(16) 0.04781(13) 0.0320(5) Uani 1.000 C C2 0.3049(5) 0.27882(18) 0.14751(16) 0.0422(6) Uani 1.000 C C3 0.3363(10) 0.1372(3) 0.1064(3) 0.0813(13) Uani 1.000 C C4 0.1794(7) 0.2909(3) 0.2674(2) 0.0611(9) Uani 1.000 H H2 0.497(5) 0.3308(19) 0.1440(16) 0.047(5) Uiso 1.000 H H3A 0.136(9) 0.100(3) 0.096(3) 0.116(13) Uiso 1.000 H H3B 0.460(6) 0.091(3) 0.163(2) 0.080(7) Uiso 1.000 H H3C 0.431(7) 0.134(3) 0.031(3) 0.109(11) Uiso 1.000 H H4A -0.014(6) 0.236(3) 0.270(2) 0.080(8) Uiso 1.000 H H4B 0.153(6) 0.386(3) 0.288(2) 0.078(8) Uiso 1.000 H H4C 0.317(5) 0.248(2) 0.324(2) 0.071(7) 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 . 116.99(13) yes O1 C1 O2 . 126.55(15) yes O1 C1 C1 3_565 123.62(15) yes O2 C1 C1 3_565 109.83(13) yes O2 C2 C3 . 105.59(19) yes O2 C2 C4 . 109.07(18) yes C3 C2 C4 . 113.8(2) no O2 C2 H2 . 104.9(11) no C3 C2 H2 . 113.1(11) no C4 C2 H2 . 109.8(11) no C2 C3 H3A . 108(2) no C2 C3 H3B . 107.7(17) no C2 C3 H3C . 110.9(18) no H3A C3 H3B . 113(3) no H3A C3 H3C . 108(3) no H3B C3 H3C . 110(2) no C2 C4 H4A . 108.8(14) no C2 C4 H4B . 110.2(14) no C2 C4 H4C . 109.5(13) no H4A C4 H4B . 114(2) no H4A C4 H4C . 104(2) no H4B C4 H4C . 110.1(19) 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 . 1.197(2) yes O2 C1 . 1.321(2) yes O2 C2 . 1.477(2) yes C1 C1 3_565 1.539(2) no C2 C3 . 1.493(4) no C2 C4 . 1.497(3) no C2 H2 . 0.99(2) no C3 H3A . 0.95(4) no C3 H3B . 0.94(3) no C3 H3C . 0.97(3) no C4 H4A . 1.01(3) no C4 H4B . 0.98(3) no C4 H4C . 0.96(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 C4 3.231(3) . no O1 C1 3.151(2) 3_665 no O1 O1 3.135(2) 3_665 no O1 O2 2.6610(19) 3_565 no O2 O1 2.6610(19) 3_565 no O1 H4B 2.76(3) . no O1 H4C 2.73(2) 2_655 no O1 H4A 2.70(3) 2_555 no O1 H2 2.378(19) . no O1 H3B 2.88(2) 2_655 no O2 H2 2.79(2) 1_455 no C1 O1 3.151(2) 3_665 no C1 C1 3.591(3) 3_665 no C4 O1 3.231(3) . no C1 H4B 2.87(2) . no H2 O1 2.378(19) . no H2 O2 2.79(2) 1_655 no H3A H4A 2.51(4) . no H3B H4C 2.51(3) . no H3B O1 2.88(2) 2_645 no H4A H3A 2.51(4) . no H4A O1 2.70(3) 2_545 no H4B O1 2.76(3) . no H4B C1 2.87(2) . no H4C H3B 2.51(3) . no H4C O1 2.73(2) 2_645 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 H2 O1 0.99(2) 2.378(19) 2.728(2) 100.0(14) 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 . . -2.0(2) no C2 O2 C1 C1 . 3_565 178.29(14) no C1 O2 C2 C3 . . -153.2(2) no C1 O2 C2 C4 . . 84.1(2) no O1 C1 C1 O1 3_565 3_565 179.98(19) no O2 C1 C1 O2 3_565 3_565 180.00(13) no O1 C1 C1 O2 3_565 3_565 0.3(2) no O2 C1 C1 O1 3_565 3_565 -0.3(2) no