#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/48/2204844.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_2204844 loop_ _publ_author_name 'Mondal, S.' 'Narasegowda, R. S.' 'Nagaraj, B.' 'Yathirajan, H. S.' 'Narasimhamurthy, T.' 'Rathore, Ravindranath S.' _publ_section_title ; 2,2'-Dipropylmalonic acid: intermolecular association via strong O---H···O hydrogen bonds ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o151 _journal_page_last o153 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C9 H16 O4' _chemical_formula_moiety 'C9 H16 O4' _chemical_formula_sum 'C9 H16 O4' _chemical_formula_weight 188.22 _chemical_melting_point 432 _chemical_name_systematic ; 2,2'-Dipropylmalonic acid ; _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 76.249(2) _cell_angle_beta 70.140(2) _cell_angle_gamma 72.355(2) _cell_formula_units_Z 2 _cell_length_a 7.6830(10) _cell_length_b 8.5490(10) _cell_length_c 9.3820(10) _cell_measurement_reflns_used 3369 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 55 _cell_measurement_theta_min 5 _cell_volume 546.04(11) _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT-Plus _computing_molecular_graphics 'ORTEPIII (Farrugia, 1997) and PLUTON (Spek, 1999)' _computing_publication_material 'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.911 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _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 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5840 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.42 _diffrn_reflns_theta_min 2.33 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.145 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 204 _exptl_crystal_size_max .55 _exptl_crystal_size_mid .22 _exptl_crystal_size_min .12 _refine_diff_density_max 0.179 _refine_diff_density_min -0.156 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 126 _refine_ls_number_reflns 2261 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0505 _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^)+(0.0805P)^2^+0.0901P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1400 _refine_ls_wR_factor_ref 0.1503 _reflns_number_gt 1784 _reflns_number_total 2261 _reflns_threshold_expression I>2s(I) _[local]_cod_data_source_file bt6565.cif _[local]_cod_data_source_block I _cod_original_cell_volume 546.05(12) _cod_database_code 2204844 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 0.0860(2) 0.07364(18) 0.79604(14) 0.0766(5) Uani d . 1 O O2 -0.03567(18) 0.44811(19) 0.71039(15) 0.0784(5) Uani d . 1 O O3 0.1097(2) 0.13697(17) 1.00235(13) 0.0745(4) Uani d . 1 O O4 0.20931(16) 0.39020(17) 0.50464(12) 0.0706(4) Uani d . 1 O C1 0.1404(2) 0.1565(2) 0.86526(17) 0.0512(4) Uani d . 1 C C2 0.2539(2) 0.27809(19) 0.75464(16) 0.0491(4) Uani d . 1 C C3 0.1413(2) 0.3764(2) 0.64235(17) 0.0538(4) Uani d . 1 C C4 0.4476(2) 0.1756(2) 0.66546(17) 0.0533(4) Uani d . 1 C H4A 0.4227 0.1063 0.6101 0.064 Uiso calc R 1 H H4B 0.5164 0.2520 0.5901 0.064 Uiso calc R 1 H C5 0.5761(3) 0.0656(2) 0.7608(2) 0.0655(5) Uani d . 1 C H5A 0.6061 0.1335 0.8142 0.079 Uiso calc R 1 H H5B 0.5093 -0.0116 0.8370 0.079 Uiso calc R 1 H C6 0.7584(3) -0.0302(3) 0.6626(3) 0.0911(7) Uani d . 1 C H6A 0.8364 -0.0989 0.7261 0.137 Uiso calc R 1 H H6B 0.8259 0.0459 0.5884 0.137 Uiso calc R 1 H H6C 0.7291 -0.0988 0.6107 0.137 Uiso calc R 1 H C7 0.2733(2) 0.3985(2) 0.84349(18) 0.0576(4) Uani d . 1 C H7A 0.1474 0.4486 0.9053 0.069 Uiso calc R 1 H H7B 0.3481 0.3359 0.9127 0.069 Uiso calc R 1 H C8 0.3661(4) 0.5356(3) 0.7421(3) 0.0910(7) Uani d . 1 C H8A 0.4900 0.4855 0.6776 0.109 Uiso calc R 1 H H8B 0.2887 0.6007 0.6755 0.109 Uiso calc R 1 H C9 0.3916(5) 0.6487(3) 0.8279(3) 0.1129(9) Uani d . 1 C H9A 0.4502 0.7321 0.7566 0.169 Uiso calc R 1 H H9B 0.4715 0.5860 0.8918 0.169 Uiso calc R 1 H H9C 0.2694 0.7009 0.8905 0.169 Uiso calc R 1 H H1 0.026(4) 0.006(3) 0.856(3) 0.108(8) Uiso d . 1 H H2 -0.094(4) 0.508(3) 0.642(3) 0.101(8) Uiso d . 1 H 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 0.1062(11) 0.0927(10) 0.0492(7) -0.0677(9) -0.0236(7) 0.0136(6) O2 0.0509(7) 0.1039(10) 0.0483(7) -0.0003(6) -0.0057(5) 0.0108(7) O3 0.0966(10) 0.0984(10) 0.0427(7) -0.0646(8) -0.0189(6) 0.0148(6) O4 0.0534(7) 0.0920(9) 0.0435(7) -0.0091(6) -0.0073(5) 0.0107(6) C1 0.0504(8) 0.0590(9) 0.0436(8) -0.0238(7) -0.0150(7) 0.0091(6) C2 0.0456(8) 0.0553(8) 0.0411(8) -0.0204(7) -0.0074(6) 0.0057(6) C3 0.0475(8) 0.0579(9) 0.0445(8) -0.0185(7) -0.0054(6) 0.0089(6) C4 0.0491(9) 0.0610(9) 0.0457(8) -0.0169(7) -0.0101(7) -0.0010(7) C5 0.0606(10) 0.0743(11) 0.0641(11) -0.0102(8) -0.0250(8) -0.0127(9) C6 0.0683(13) 0.1114(17) 0.0927(15) 0.0091(12) -0.0359(11) -0.0354(13) C7 0.0573(9) 0.0600(10) 0.0492(9) -0.0237(8) -0.0031(7) -0.0028(7) C8 0.1131(18) 0.0881(14) 0.0772(14) -0.0656(14) -0.0043(12) -0.0034(11) C9 0.132(2) 0.0840(16) 0.124(2) -0.0580(16) -0.0058(17) -0.0237(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.297(2) O1 H1 0.83(3) O2 C3 1.313(2) O2 H2 0.88(3) O3 C1 1.2056(18) O4 C3 1.2093(18) C1 C2 1.5297(19) C2 C3 1.524(2) C2 C7 1.537(2) C2 C4 1.547(2) C4 C5 1.515(2) C4 H4A 0.9700 C4 H4B 0.9700 C5 C6 1.506(3) C5 H5A 0.9700 C5 H5B 0.9700 C6 H6A 0.9600 C6 H6B 0.9600 C6 H6C 0.9600 C7 C8 1.517(2) C7 H7A 0.9700 C7 H7B 0.9700 C8 C9 1.487(3) C8 H8A 0.9700 C8 H8B 0.9700 C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 H1 113.2(18) C3 O2 H2 110.4(17) O3 C1 O1 123.73(14) O3 C1 C2 123.18(14) O1 C1 C2 113.06(13) C3 C2 C1 107.15(12) C3 C2 C7 109.01(13) C1 C2 C7 109.91(12) C3 C2 C4 109.01(12) C1 C2 C4 107.97(13) C7 C2 C4 113.58(13) O4 C3 O2 123.42(15) O4 C3 C2 123.45(14) O2 C3 C2 113.11(13) C5 C4 C2 116.08(13) C5 C4 H4A 108.3 C2 C4 H4A 108.3 C5 C4 H4B 108.3 C2 C4 H4B 108.3 H4A C4 H4B 107.4 C6 C5 C4 111.42(16) C6 C5 H5A 109.3 C4 C5 H5A 109.3 C6 C5 H5B 109.3 C4 C5 H5B 109.3 H5A C5 H5B 108.0 C5 C6 H6A 109.5 C5 C6 H6B 109.5 H6A C6 H6B 109.5 C5 C6 H6C 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 C8 C7 C2 114.01(14) C8 C7 H7A 108.8 C2 C7 H7A 108.8 C8 C7 H7B 108.8 C2 C7 H7B 108.8 H7A C7 H7B 107.6 C9 C8 C7 114.15(19) C9 C8 H8A 108.7 C7 C8 H8A 108.7 C9 C8 H8B 108.7 C7 C8 H8B 108.7 H8A C8 H8B 107.6 C8 C9 H9A 109.5 C8 C9 H9B 109.5 H9A C9 H9B 109.5 C8 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 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 O3 C1 C2 C3 -133.23(17) O1 C1 C2 C3 48.74(18) O3 C1 C2 C7 -14.9(2) O1 C1 C2 C7 167.06(14) O3 C1 C2 C4 109.48(18) O1 C1 C2 C4 -68.55(17) C1 C2 C3 O4 -127.53(17) C7 C2 C3 O4 113.56(18) C4 C2 C3 O4 -10.9(2) C1 C2 C3 O2 54.07(18) C7 C2 C3 O2 -64.83(17) C4 C2 C3 O2 170.68(14) C3 C2 C4 C5 -178.15(14) C1 C2 C4 C5 -62.07(18) C7 C2 C4 C5 60.09(18) C2 C4 C5 C6 178.96(16) C3 C2 C7 C8 -56.9(2) C1 C2 C7 C8 -174.03(17) C4 C2 C7 C8 64.9(2) C2 C7 C8 C9 -177.9(2) 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 O1 H1 O3 2_557 0.83(3) 1.85(3) 2.678(2) 176(3) y O2 H2 O4 2_566 0.87(3) 1.80(3) 2.673(2) 175(3) y