#------------------------------------------------------------------------------ #$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176787 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/51/2215125.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_2215125 loop_ _publ_author_name 'Sudarshan Mahapatra' 'Srijita Basu Mallik' 'G. Venkateswara Rao' 'G. Chandrasekara Reddy' 'Guru Row, T. N.' _publ_section_title ; Garcinia lactone ; _journal_coeditor_code HB2498 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3869 _journal_page_last o3869 _journal_paper_doi 10.1107/S160053680703838X _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C6 H6 O7' _chemical_formula_moiety 'C6 H6 O7' _chemical_formula_sum 'C6 H6 O7' _chemical_formula_weight 190.11 _chemical_melting_point .449E-305 _chemical_name_common 'Garcinia lactone' _chemical_name_systematic ; (2S,3S)-3-hydroxy-5-oxo-2,3,4,5-tetrahydrofuran-2,3-dicarboxylic acid ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.2657(10) _cell_length_b 8.6591(14) _cell_length_c 13.504(2) _cell_measurement_reflns_used 545 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 27.98 _cell_measurement_theta_min 0.99 _cell_volume 732.7(2) _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_collection 'SMART (Bruker, 2004)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _diffrn_ambient_temperature 292(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method '\f and \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 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5568 _diffrn_reflns_reduction_process ' ?' _diffrn_reflns_theta_full 25.66 _diffrn_reflns_theta_max 25.66 _diffrn_reflns_theta_min 2.79 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.214 _refine_diff_density_min -0.171 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 836 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.101 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0271 _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^)+(0.0319P)^2^+0.2219P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.0663 _reflns_number_gt 810 _reflns_number_total 836 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hb2498.cif _cod_data_source_block I _cod_database_code 2215125 _cod_database_fobs_code 2215125 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z 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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy O O5 1.0046(2) -0.15092(19) 0.14395(13) 0.0390(4) Uani d . 1 O O6 0.4251(2) 0.00593(19) -0.05515(12) 0.0350(4) Uani d . 1 O O3 0.7966(2) 0.09450(18) 0.23129(10) 0.0281(4) Uani d . 1 H H3 0.9172 0.1169 0.2126 0.042 Uiso calc R 1 O O2 0.4978(2) 0.21068(16) 0.08633(10) 0.0259(3) Uani d . 1 O O7 0.7760(3) -0.03680(19) -0.07537(11) 0.0336(4) Uani d . 1 H H7 0.7377 -0.0840 -0.1249 0.050 Uiso calc R 1 O O4 0.6882(2) -0.25433(17) 0.10495(12) 0.0339(4) Uani d . 1 H H4 0.7592 -0.3321 0.0942 0.051 Uiso calc R 1 O O1 0.1911(2) 0.19661(19) 0.16734(13) 0.0371(4) Uani d . 1 C C6 0.8148(3) -0.1423(2) 0.13577(15) 0.0254(5) Uani d . 1 C C2 0.4591(3) -0.0075(2) 0.18784(15) 0.0250(5) Uani d . 1 H H2A 0.3931 -0.0972 0.1576 0.030 Uiso calc R 1 H H2B 0.4451 -0.0149 0.2592 0.030 Uiso calc R 1 C C1 0.3614(3) 0.1399(2) 0.14948(15) 0.0252(4) Uani d . 1 C C3 0.6927(3) 0.0069(2) 0.15732(14) 0.0213(4) Uani d . 1 C C4 0.6711(3) 0.1092(2) 0.06284(14) 0.0216(4) Uani d . 1 H H4A 0.8023 0.1681 0.0515 0.026 Uiso calc R 1 C C5 0.6089(3) 0.0196(2) -0.03010(14) 0.0243(5) Uani d . 1 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 O5 0.0218(8) 0.0381(9) 0.0570(10) 0.0038(7) -0.0013(8) 0.0039(9) O6 0.0283(9) 0.0377(9) 0.0389(9) -0.0021(8) -0.0084(7) -0.0072(7) O3 0.0240(7) 0.0391(9) 0.0212(7) -0.0047(7) -0.0007(6) -0.0034(6) O2 0.0271(8) 0.0240(7) 0.0265(7) 0.0046(6) 0.0039(7) 0.0023(6) O7 0.0336(9) 0.0420(9) 0.0253(7) 0.0052(7) 0.0015(7) -0.0095(7) O4 0.0287(8) 0.0251(7) 0.0480(10) 0.0020(7) -0.0003(7) -0.0072(7) O1 0.0246(8) 0.0359(9) 0.0510(10) 0.0055(8) 0.0084(8) -0.0037(8) C6 0.0244(10) 0.0287(11) 0.0230(10) 0.0010(9) 0.0000(9) 0.0061(9) C2 0.0221(10) 0.0274(10) 0.0254(10) 0.0003(9) 0.0036(8) 0.0016(9) C1 0.0228(10) 0.0264(10) 0.0263(10) -0.0015(9) -0.0008(9) -0.0039(9) C3 0.0207(10) 0.0260(10) 0.0173(9) -0.0030(10) -0.0003(8) 0.0010(8) C4 0.0199(9) 0.0239(9) 0.0209(10) -0.0009(9) 0.0016(8) 0.0006(8) C5 0.0279(11) 0.0233(10) 0.0215(10) 0.0005(9) 0.0002(8) 0.0019(8) 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 C3 O3 H3 109.5 C1 O2 C4 109.88(15) C5 O7 H7 109.5 C6 O4 H4 109.5 O5 C6 O4 125.5(2) O5 C6 C3 122.1(2) O4 C6 C3 112.34(16) C1 C2 C3 103.13(17) C1 C2 H2A 111.1 C3 C2 H2A 111.1 C1 C2 H2B 111.1 C3 C2 H2B 111.1 H2A C2 H2B 109.1 O1 C1 O2 120.2(2) O1 C1 C2 129.7(2) O2 C1 C2 110.10(17) O3 C3 C2 107.16(16) O3 C3 C6 110.94(16) C2 C3 C6 117.51(17) O3 C3 C4 108.30(16) C2 C3 C4 100.64(15) C6 C3 C4 111.56(15) O2 C4 C5 107.47(15) O2 C4 C3 103.47(15) C5 C4 C3 114.01(16) O2 C4 H4A 110.5 C5 C4 H4A 110.5 C3 C4 H4A 110.5 O6 C5 O7 126.6(2) O6 C5 C4 121.64(18) O7 C5 C4 111.72(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O5 C6 1.197(2) O6 C5 1.206(3) O3 C3 1.413(2) O3 H3 0.8200 O2 C1 1.354(2) O2 C4 1.433(2) O7 C5 1.307(3) O7 H7 0.8200 O4 C6 1.320(3) O4 H4 0.8200 O1 C1 1.199(3) C6 C3 1.530(3) C2 C1 1.507(3) C2 C3 1.526(3) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.559(3) C4 C5 1.526(3) C4 H4A 0.9800 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 O3 H3 O1 1_655 0.82 1.95 2.764(2) 173 yes O4 H4 O6 3_545 0.82 1.90 2.721(2) 174 yes O7 H7 O3 2_654 0.82 1.96 2.697(2) 150 yes C4 H4A O2 3_555 0.98 2.46 3.268(2) 139 yes C2 H2A O4 . 0.97 2.40 2.808(3) 104 yes C2 H2A O5 1_455 0.97 2.49 3.163(2) 127 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 C4 O2 C1 O1 -169.51(18) C4 O2 C1 C2 10.6(2) C3 C2 C1 O1 -166.8(2) C3 C2 C1 O2 13.1(2) C1 C2 C3 O3 84.37(18) C1 C2 C3 C6 -150.01(17) C1 C2 C3 C4 -28.73(19) O5 C6 C3 O3 -30.7(3) O4 C6 C3 O3 151.34(16) O5 C6 C3 C2 -154.5(2) O4 C6 C3 C2 27.6(2) O5 C6 C3 C4 90.1(3) O4 C6 C3 C4 -87.8(2) C1 O2 C4 C5 91.59(18) C1 O2 C4 C3 -29.35(19) O3 C3 C4 O2 -76.88(18) C2 C3 C4 O2 35.34(19) C6 C3 C4 O2 160.76(15) O3 C3 C4 C5 166.72(15) C2 C3 C4 C5 -81.1(2) C6 C3 C4 C5 44.4(2) O2 C4 C5 O6 -20.9(3) C3 C4 C5 O6 93.2(2) O2 C4 C5 O7 159.30(16) C3 C4 C5 O7 -86.7(2)