#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200095.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_2200095 loop_ _publ_author_name 'Bond, Andrew D.' 'Edwards, Marc R.' 'Jones, William' _publ_section_title ; Azelaic acid ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o143 _journal_page_last o144 _journal_volume 57 _journal_year 2001 _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 383.0(10) _chemical_name_common 'azelaic acid' _chemical_name_systematic 'heptane-1,7-dicarboxylic acid' _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 110.559(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 22.622(2) _cell_length_b 4.7348(2) _cell_length_c 9.6864(7) _cell_measurement_reflns_used 2161 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.00 _cell_volume 971.44(12) _computing_cell_refinement 'HKL SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction 'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'XP (Sheldrick, 1993) and CAMERON (Watkin et al., 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 180(2) _diffrn_measured_fraction_theta_full .984 _diffrn_measured_fraction_theta_max .984 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin-slice \w and \f' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .039 _diffrn_reflns_av_sigmaI/netI .0387 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3154 _diffrn_reflns_theta_full 27.43 _diffrn_reflns_theta_max 27.43 _diffrn_reflns_theta_min 3.85 _exptl_absorpt_coefficient_mu .100 _exptl_absorpt_correction_T_max .994 _exptl_absorpt_correction_T_min .907 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 408 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .06 _refine_diff_density_max .249 _refine_diff_density_min -.187 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 64 _refine_ls_number_reflns 1085 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.091 _refine_ls_R_factor_all .047 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max .010 _refine_ls_shift/su_mean .003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.5150P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .096 _reflns_number_gt 913 _reflns_number_total 1085 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6003.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '382-384' was changed to '383.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '382-384' was changed to '383.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 971.50(10) _cod_database_code 2200095 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .18109(4) .17201(19) .01920(10) .0312(3) Uani d . 1 . . O O2 .24341(4) .54364(19) .11100(10) .0314(3) Uani d . 1 . . O H1 .2682(9) .465(4) .057(2) .079(6) Uiso d . 1 . . H C1 .19218(5) .3923(3) .09015(12) .0244(3) Uani d . 1 . . C C2 .14794(6) .5227(3) .15576(14) .0307(3) Uani d . 1 . . C H2A .1264 .6833 .0927 .037 Uiso calc R 1 . . H H2B .1732 .6004 .2536 .037 Uiso calc R 1 . . H C3 .09798(5) .3284(3) .17462(14) .0282(3) Uani d . 1 . . C H3A .1183 .1874 .2523 .034 Uiso calc R 1 . . H H3B .0767 .2257 .0813 .034 Uiso calc R 1 . . H C4 .04919(5) .4949(3) .21683(13) .0270(3) Uani d . 1 . . C H4A .0715 .6108 .3048 .032 Uiso calc R 1 . . H H4B .0272 .6258 .1353 .032 Uiso calc R 1 . . H C5 .0000 .3150(4) .2500 .0294(4) Uani d S 1 . . C H5A -.0213 .1920 .1643 .035 Uiso d R 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 .0272(5) .0337(5) .0397(5) -.0021(4) .0205(4) -.0071(4) O2 .0262(5) .0340(5) .0429(5) -.0043(4) .0235(4) -.0055(4) C1 .0213(6) .0289(6) .0267(6) .0018(5) .0132(4) .0030(5) C2 .0269(6) .0322(7) .0424(7) -.0027(5) .0240(6) -.0064(5) C3 .0244(6) .0299(7) .0373(7) .0008(5) .0196(5) -.0003(5) C4 .0222(6) .0300(7) .0348(7) .0002(5) .0175(5) -.0012(5) C5 .0251(9) .0317(9) .0389(9) .000 .0206(7) .000 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 . 1.2255(15) no O2 C1 . 1.3166(14) no O2 H1 . .96(2) no C1 C2 . 1.4944(16) no C2 C3 . 1.5172(16) no C2 H2A . .9900 no C2 H2B . .9900 no C3 C4 . 1.5244(15) no C3 H3A . .9900 no C3 H3B . .9900 no C4 C5 . 1.5224(14) no C4 H4A . .9900 no C4 H4B . .9900 no C5 C4 2 1.5224(14) no C5 H5A . .9899 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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_1 _geom_angle _geom_angle_publ_flag C1 O2 H1 . 110.9(12) no O1 C1 O2 . 123.02(10) no O1 C1 C2 . 123.67(10) no O2 C1 C2 . 113.25(10) no C1 C2 C3 . 116.05(10) no C1 C2 H2A . 108.3 no C3 C2 H2A . 108.3 no C1 C2 H2B . 108.3 no C3 C2 H2B . 108.3 no H2A C2 H2B . 107.4 no C2 C3 C4 . 111.04(10) no C2 C3 H3A . 109.4 no C4 C3 H3A . 109.4 no C2 C3 H3B . 109.4 no C4 C3 H3B . 109.4 no H3A C3 H3B . 108.0 no C5 C4 C3 . 114.78(11) no C5 C4 H4A . 108.6 no C3 C4 H4A . 108.6 no C5 C4 H4B . 108.6 no C3 C4 H4B . 108.6 no H4A C4 H4B . 107.5 no C4 C5 C4 2 111.97(14) no C4 C5 H5A 2 109.2 no C4 C5 H5A . 109.2 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 O2 H1 O1 7 .96(2) 1.70(2) 2.6576(12) 173.5(17) 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_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C3 . 19.17(18) no O2 C1 C2 C3 . -163.41(10) no C1 C2 C3 C4 . -170.14(11) no C2 C3 C4 C5 . -175.40(9) no C3 C4 C5 C4 2 -176.92(11) no