#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/72/1507257.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1507257 loop_ _publ_author_name 'P\'erez, Cirilo' 'Rodr\'iguez, Mat\'ias L' 'Foces-Foces, Concepci\'on' 'P\'erez-Hern\'andez, Natalia' 'P\'erez, Ricardo' 'Mart\'in, Julio D' _publ_section_title ; Controlled incorporation of water molecules into carboxy hydrogen-bond networks: a designed approach. ; _journal_issue 5 _journal_name_full 'Organic letters' _journal_page_first 641 _journal_page_last 644 _journal_paper_doi 10.1021/ol027332o _journal_volume 5 _journal_year 2003 _chemical_formula_sum 'C13 H22 O6' _chemical_formula_weight 274.31 _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 88.339(16) _cell_angle_beta 83.20(2) _cell_angle_gamma 73.26(3) _cell_formula_units_Z 2 _cell_length_a 6.484(3) _cell_length_b 7.662(2) _cell_length_c 14.752(2) _cell_measurement_temperature 293(2) _cell_volume 696.9(4) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3083 _diffrn_reflns_theta_full 26.29 _diffrn_reflns_theta_max 26.29 _diffrn_reflns_theta_min 2.78 _exptl_absorpt_coefficient_mu 0.103 _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _refine_diff_density_max 0.219 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.039 _refine_ls_extinction_coef 0.000(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 2821 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.890 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0457 _refine_ls_shift/su_max 0.475 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.3959P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1134 _refine_ls_wR_factor_ref 0.1416 _reflns_number_gt 1755 _reflns_number_total 2821 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol027332osi20021122_115846.cif _cod_data_source_block 1f_(acidf1+H2O) _cod_database_code 1507257 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O1 O 0.3409(2) 0.1146(2) 0.30967(10) 0.0363(4) Uani 1 1 d . O5 O 0.6904(3) 0.0120(3) 0.40381(14) 0.0692(6) Uani 1 1 d . O3 O 0.5961(3) 0.4050(3) 0.09609(12) 0.0564(5) Uani 1 1 d . O4 O 0.2544(3) 0.5074(3) 0.06888(14) 0.0711(7) Uani 1 1 d . H4 H 0.3125 0.5292 0.0191 0.141(18) Uiso 1 1 calc R O2 O 0.5843(4) 0.2729(3) 0.48042(14) 0.0627(6) Uani 1 1 d . H2 H 0.6715 0.2173 0.5146 0.103(14) Uiso 1 1 calc R O6 O 0.1484(4) -0.1347(3) 0.40074(15) 0.0583(6) Uani 1 1 d . C1 C 0.3937(4) 0.2543(3) 0.35770(14) 0.0353(5) Uani 1 1 d . C2 C 0.1865(4) 0.3724(4) 0.41016(15) 0.0439(6) Uani 1 1 d . H2A H 0.2142 0.4774 0.4360 0.039(6) Uiso 1 1 calc R H2B H 0.1369 0.3032 0.4598 0.053(7) Uiso 1 1 calc R C3 C 0.0116(4) 0.4357(4) 0.34487(16) 0.0498(7) Uani 1 1 d . H3A H -0.0560 0.3395 0.3394 0.056(8) Uiso 1 1 calc R H3B H -0.0995 0.5411 0.3715 0.052(7) Uiso 1 1 calc R C4 C 0.0962(4) 0.4859(4) 0.24902(16) 0.0448(6) Uani 1 1 d . H4A H 0.1017 0.6110 0.2501 0.058(8) Uiso 1 1 calc R H4B H -0.0061 0.4795 0.2071 0.056(8) Uiso 1 1 calc R C5 C 0.3221(3) 0.3631(3) 0.21223(14) 0.0336(5) Uani 1 1 d . C6 C 0.4756(4) 0.3671(3) 0.28270(15) 0.0355(5) Uani 1 1 d . H6A H 0.6259 0.3103 0.2596 0.032(6) Uiso 1 1 calc R H6B H 0.4586 0.4902 0.3031 0.033(6) Uiso 1 1 calc R C7 C 0.3995(4) 0.4281(3) 0.11953(15) 0.0386(5) Uani 1 1 d . C8 C 0.5717(4) 0.1630(4) 0.41678(16) 0.0403(6) Uani 1 1 d . C9 C 0.3380(3) 0.1549(3) 0.21264(14) 0.0331(5) Uani 1 1 d . C10 C 0.5509(4) 0.0362(3) 0.16254(17) 0.0449(6) Uani 1 1 d . H10A H 0.5509 0.0604 0.0976 0.058(8) Uiso 1 1 calc R H10B H 0.6705 0.0713 0.1826 0.058(8) Uiso 1 1 calc R C11 C 0.5889(6) -0.1663(4) 0.1776(3) 0.0778(10) Uani 1 1 d . H11A H 0.5868 -0.1917 0.2417 0.089(12) Uiso 1 1 calc R H11B H 0.7272 -0.2313 0.1465 0.091(12) Uiso 1 1 calc R H11C H 0.4767 -0.2043 0.1540 0.132(18) Uiso 1 1 calc R C12 C 0.1410(4) 0.1069(4) 0.18386(17) 0.0473(6) Uani 1 1 d . H12A H 0.1452 -0.0146 0.2057 0.060(8) Uiso 1 1 calc R H12B H 0.0107 0.1906 0.2142 0.055(8) Uiso 1 1 calc R C13 C 0.1235(5) 0.1125(6) 0.08183(19) 0.0733(10) Uani 1 1 d . H13A H 0.2482 0.0260 0.0510 0.116(15) Uiso 1 1 calc R H13B H 0.1167 0.2326 0.0593 0.141(19) Uiso 1 1 calc R H13C H -0.0053 0.0825 0.0708 0.117(14) Uiso 1 1 calc R H6OA H 0.199(7) -0.053(6) 0.369(3) 0.107(14) Uiso 1 1 d . H6OB H 0.021(8) -0.091(7) 0.413(3) 0.13(2) Uiso 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0434(9) 0.0428(9) 0.0289(8) 0.0050(7) -0.0060(7) -0.0220(7) O5 0.0621(13) 0.0663(14) 0.0732(14) -0.0069(11) -0.0326(11) 0.0014(11) O3 0.0452(11) 0.0755(13) 0.0453(10) 0.0213(9) 0.0037(8) -0.0177(9) O4 0.0545(12) 0.1090(18) 0.0431(11) 0.0363(11) -0.0082(9) -0.0149(11) O2 0.0788(15) 0.0588(12) 0.0576(12) 0.0019(10) -0.0355(11) -0.0200(11) O6 0.0609(14) 0.0685(14) 0.0556(12) 0.0224(10) -0.0212(10) -0.0308(12) C1 0.0371(12) 0.0423(13) 0.0293(11) 0.0014(9) -0.0046(9) -0.0157(10) C2 0.0468(14) 0.0557(16) 0.0288(11) -0.0022(11) 0.0003(10) -0.0158(12) C3 0.0378(14) 0.0675(18) 0.0369(13) -0.0069(12) 0.0046(11) -0.0066(13) C4 0.0403(14) 0.0484(16) 0.0397(13) -0.0009(11) -0.0032(11) -0.0036(11) C5 0.0330(12) 0.0396(13) 0.0275(11) 0.0034(9) -0.0017(9) -0.0103(10) C6 0.0376(13) 0.0370(12) 0.0350(12) 0.0046(10) -0.0052(10) -0.0159(10) C7 0.0394(14) 0.0436(14) 0.0320(12) 0.0071(10) -0.0033(10) -0.0116(11) C8 0.0438(14) 0.0484(15) 0.0335(12) 0.0091(11) -0.0065(10) -0.0211(12) C9 0.0331(12) 0.0410(13) 0.0261(10) 0.0019(9) -0.0022(9) -0.0124(10) C10 0.0408(14) 0.0447(15) 0.0458(14) -0.0034(11) -0.0013(11) -0.0079(11) C11 0.079(2) 0.0453(18) 0.095(3) -0.0068(17) 0.003(2) -0.0003(17) C12 0.0431(14) 0.0643(18) 0.0396(13) -0.0055(12) -0.0025(11) -0.0239(13) C13 0.060(2) 0.127(3) 0.0433(16) -0.0142(19) -0.0115(14) -0.040(2) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 C9 111.33(15) C7 O4 H4 109.5 C8 O2 H2 109.5 H6OA O6 H6OB 107(4) O1 C1 C2 108.44(18) O1 C1 C8 108.49(19) C2 C1 C8 114.56(19) O1 C1 C6 104.62(17) C2 C1 C6 109.3(2) C8 C1 C6 110.91(18) C1 C2 C3 109.18(19) C1 C2 H2A 109.8 C3 C2 H2A 109.8 C1 C2 H2B 109.8 C3 C2 H2B 109.8 H2A C2 H2B 108.3 C4 C3 C2 114.4(2) C4 C3 H3A 108.7 C2 C3 H3A 108.7 C4 C3 H3B 108.7 C2 C3 H3B 108.7 H3A C3 H3B 107.6 C3 C4 C5 114.38(19) C3 C4 H4A 108.7 C5 C4 H4A 108.7 C3 C4 H4B 108.7 C5 C4 H4B 108.7 H4A C4 H4B 107.6 C7 C5 C6 111.35(18) C7 C5 C4 111.11(18) C6 C5 C4 107.19(18) C7 C5 C9 112.67(18) C6 C5 C9 100.36(17) C4 C5 C9 113.56(18) C1 C6 C5 99.48(17) C1 C6 H6A 111.9 C5 C6 H6A 111.9 C1 C6 H6B 111.9 C5 C6 H6B 111.9 H6A C6 H6B 109.6 O3 C7 O4 122.6(2) O3 C7 C5 120.4(2) O4 C7 C5 117.0(2) O5 C8 O2 124.5(2) O5 C8 C1 124.0(2) O2 C8 C1 111.4(2) O1 C9 C10 107.64(18) O1 C9 C12 106.51(17) C10 C9 C12 111.5(2) O1 C9 C5 101.01(16) C10 C9 C5 113.36(18) C12 C9 C5 115.68(19) C11 C10 C9 114.1(2) C11 C10 H10A 108.7 C9 C10 H10A 108.7 C11 C10 H10B 108.7 C9 C10 H10B 108.7 H10A C10 H10B 107.6 C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C13 C12 C9 115.7(2) C13 C12 H12A 108.4 C9 C12 H12A 108.4 C13 C12 H12B 108.4 C9 C12 H12B 108.4 H12A C12 H12B 107.4 C12 C13 H13A 109.5 C12 C13 H13B 109.5 H13A C13 H13B 109.5 C12 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.441(3) O1 C9 1.457(2) O5 C8 1.197(3) O3 C7 1.243(3) O4 C7 1.274(3) O4 H4 0.8200 O2 C8 1.304(3) O2 H2 0.8200 O6 H6OA 0.88(4) O6 H6OB 0.80(5) C1 C2 1.522(3) C1 C8 1.523(3) C1 C6 1.524(3) C2 C3 1.537(3) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.534(3) C3 H3A 0.9700 C3 H3B 0.9700 C4 C5 1.541(3) C4 H4A 0.9700 C4 H4B 0.9700 C5 C7 1.520(3) C5 C6 1.528(3) C5 C9 1.568(3) C6 H6A 0.9700 C6 H6B 0.9700 C9 C10 1.534(3) C9 C12 1.535(3) C10 C11 1.513(4) C10 H10A 0.9700 C10 H10B 0.9700 C11 H11A 0.9600 C11 H11B 0.9600 C11 H11C 0.9600 C12 C13 1.521(4) C12 H12A 0.9700 C12 H12B 0.9700 C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 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_site_symmetry_A O4 H4 O3 0.82 1.84 2.652(3) 171.9 2_665 O2 H2 O6 0.82 1.79 2.599(3) 169.7 2_656 O6 H6OA O1 0.88(4) 1.93(4) 2.800(3) 173(4) . O6 H6OB O5 0.80(5) 2.08(5) 2.852(4) 163(5) 1_455 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 C9 O1 C1 C2 104.08(19) C9 O1 C1 C8 -130.93(18) C9 O1 C1 C6 -12.5(2) O1 C1 C2 C3 -51.4(2) C8 C1 C2 C3 -172.7(2) C6 C1 C2 C3 62.1(3) C1 C2 C3 C4 -39.1(3) C2 C3 C4 C5 37.3(3) C3 C4 C5 C7 -176.8(2) C3 C4 C5 C6 -54.9(3) C3 C4 C5 C9 55.0(3) O1 C1 C6 C5 37.4(2) C2 C1 C6 C5 -78.5(2) C8 C1 C6 C5 154.19(19) C7 C5 C6 C1 -166.49(19) C4 C5 C6 C1 71.8(2) C9 C5 C6 C1 -47.0(2) C6 C5 C7 O3 29.8(3) C4 C5 C7 O3 149.2(2) C9 C5 C7 O3 -82.1(3) C6 C5 C7 O4 -149.5(2) C4 C5 C7 O4 -30.1(3) C9 C5 C7 O4 98.6(3) O1 C1 C8 O5 21.1(3) C2 C1 C8 O5 142.4(3) C6 C1 C8 O5 -93.3(3) O1 C1 C8 O2 -161.82(19) C2 C1 C8 O2 -40.5(3) C6 C1 C8 O2 83.8(2) C1 O1 C9 C10 101.8(2) C1 O1 C9 C12 -138.46(19) C1 O1 C9 C5 -17.3(2) C7 C5 C9 O1 158.44(17) C6 C5 C9 O1 39.92(19) C4 C5 C9 O1 -74.1(2) C7 C5 C9 C10 43.6(2) C6 C5 C9 C10 -74.9(2) C4 C5 C9 C10 171.03(19) C7 C5 C9 C12 -87.1(2) C6 C5 C9 C12 154.43(18) C4 C5 C9 C12 40.4(2) O1 C9 C10 C11 57.9(3) C12 C9 C10 C11 -58.6(3) C5 C9 C10 C11 168.7(2) O1 C9 C12 C13 -171.6(3) C10 C9 C12 C13 -54.4(3) C5 C9 C12 C13 77.1(3)