#------------------------------------------------------------------------------ #$Date: 2015-03-06 01:22:47 +0200 (Fri, 06 Mar 2015) $ #$Revision: 133096 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/81/1518142.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_1518142 loop_ _publ_author_name 'Maeno, Mayaka' 'Tokunaga, Etsuko' 'Yamamoto, Takeshi' 'Suzuki, Toshiya' 'Ogino, Yoshiyuki' 'Ito, Emi' 'Shiro, Motoo' 'Asahi, Toru' 'Shibata, Norio' _publ_section_title ; Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications ; _journal_issue 2 _journal_name_full 'Chem. Sci.' _journal_page_first 1043 _journal_paper_doi 10.1039/C4SC03047H _journal_volume 6 _journal_year 2015 _chemical_formula_moiety 'C13 H10 N2 O4 ' _chemical_formula_sum 'C13 H10 N2 O4' _chemical_formula_weight 258.23 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90.0000 _cell_angle_beta 102.762(2) _cell_angle_gamma 90.0000 _cell_formula_units_Z 4 _cell_length_a 8.3156(3) _cell_length_b 9.9732(4) _cell_length_c 14.5740(5) _cell_measurement_reflns_used 7535 _cell_measurement_temperature 93.1 _cell_measurement_theta_max 68.2 _cell_measurement_theta_min 4.4 _cell_volume 1178.81(8) _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku & RAC 2007)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _computing_publication_material 'CrystalStructure (Rigaku & RAC 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 93.1 _diffrn_detector_area_resol_mean 10.00 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Rigaku VariMax RAPID' _diffrn_measurement_method \w _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 12229 _diffrn_reflns_theta_full 68.25 _diffrn_reflns_theta_max 68.25 _exptl_absorpt_coefficient_mu 0.931 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_correction_T_min 0.688 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 536.00 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.40 _refine_diff_density_min -0.21 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 173 _refine_ls_number_reflns 2122 _refine_ls_R_factor_gt 0.0467 _refine_ls_shift/su_max 0.0000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1212 _reflns_number_gt 1530 _reflns_number_total 2122 _reflns_threshold_expression F^2^>2.0\s(F^2^) _[local]_cod_data_source_file c4sc03047h2.cif _[local]_cod_data_source_block RS-revised _[local]_cod_chemical_formula_sum_orig 'C13 H10 N2 O4 ' _cod_depositor_comments 'Adding full bibliography for 1518142--1518147.cif.' _cod_original_cell_volume 1178.81(7) _cod_database_code 1518142 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+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 0.38781(16) 0.44137(12) 0.36954(10) 0.0418(4) Uani 1.00 1 d . O2 O 0.53914(17) 0.05596(12) 0.24160(10) 0.0410(4) Uani 1.00 1 d . O3 O 0.41030(15) 0.42300(12) 0.15938(9) 0.0348(3) Uani 1.00 1 d . O4 O -0.13441(16) 0.38435(12) 0.03562(10) 0.0394(3) Uani 1.00 1 d . N1 N 0.4192(2) 0.24004(14) 0.29688(12) 0.0330(4) Uani 1.00 1 d . N2 N 0.13674(18) 0.40211(13) 0.10034(11) 0.0297(4) Uani 1.00 1 d . H2N H 0.1425 0.4669 0.0602 0.036 Uiso 1.00 1 c R C1 C 0.4718(2) 0.34512(18) 0.35945(14) 0.0329(4) Uani 1.00 1 d . C2 C 0.6455(2) 0.31558(18) 0.40705(14) 0.0315(4) Uani 1.00 1 d . C3 C 0.7551(2) 0.38455(19) 0.47490(14) 0.0361(5) Uani 1.00 1 d . H3 H 0.7249 0.4659 0.5005 0.043 Uiso 1.00 1 c R C4 C 0.9126(2) 0.3303(2) 0.50484(15) 0.0407(5) Uani 1.00 1 d . H4 H 0.9915 0.3758 0.5516 0.049 Uiso 1.00 1 c R C5 C 0.9561(2) 0.2112(2) 0.46749(14) 0.0396(5) Uani 1.00 1 d . H5 H 1.0641 0.1764 0.4893 0.047 Uiso 1.00 1 c R C6 C 0.8442(2) 0.14159(19) 0.39862(14) 0.0343(5) Uani 1.00 1 d . H6 H 0.8733 0.0597 0.3731 0.041 Uiso 1.00 1 c R C7 C 0.6898(2) 0.19667(18) 0.36918(13) 0.0309(4) Uani 1.00 1 d . C8 C 0.5480(2) 0.14990(19) 0.29523(14) 0.0319(4) Uani 1.00 1 d . C9 C 0.2718(2) 0.24380(18) 0.22179(15) 0.0348(5) Uani 1.00 1 d . H9 H 0.2732 0.1620 0.1823 0.042 Uiso 1.00 1 c R C10 C 0.2822(2) 0.36463(18) 0.16027(14) 0.0304(4) Uani 1.00 1 d . C11 C -0.0169(2) 0.34803(17) 0.09717(14) 0.0314(4) Uani 1.00 1 d . C12 C -0.0315(2) 0.24494(17) 0.16986(15) 0.0341(5) Uani 1.00 1 d . H12A H -0.0411 0.1553 0.1399 0.041 Uiso 1.00 1 c R H12B H -0.1344 0.2618 0.1916 0.041 Uiso 1.00 1 c R C13 C 0.1108(2) 0.24274(19) 0.25434(15) 0.0389(5) Uani 1.00 1 d . H13A H 0.1045 0.1612 0.2922 0.047 Uiso 1.00 1 c R H13B H 0.1051 0.3221 0.2943 0.047 Uiso 1.00 1 c R 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 0.0453(8) 0.0339(7) 0.0479(10) 0.0109(6) 0.0139(7) 0.0023(6) O2 0.0523(9) 0.0286(7) 0.0424(9) -0.0033(6) 0.0112(7) -0.0036(6) O3 0.0352(7) 0.0306(7) 0.0390(9) -0.0065(5) 0.0092(6) 0.0011(6) O4 0.0350(8) 0.0373(7) 0.0425(9) -0.0042(6) 0.0013(6) 0.0086(6) N1 0.0355(9) 0.0271(8) 0.0353(10) -0.0013(6) 0.0054(7) 0.0023(7) N2 0.0343(9) 0.0235(8) 0.0317(10) -0.0028(6) 0.0082(7) 0.0037(7) C1 0.0361(11) 0.0294(10) 0.0350(12) 0.0056(8) 0.0116(9) 0.0081(9) C2 0.0368(11) 0.0256(9) 0.0340(12) 0.0014(8) 0.0119(9) 0.0031(9) C3 0.0461(12) 0.0291(10) 0.0339(12) -0.0012(8) 0.0109(10) -0.0012(9) C4 0.0434(12) 0.0429(12) 0.0348(12) -0.0080(9) 0.0066(10) 0.0034(10) C5 0.0357(11) 0.0434(12) 0.0402(13) 0.0031(8) 0.0098(10) 0.0125(10) C6 0.0373(11) 0.0286(10) 0.0398(12) 0.0063(8) 0.0145(9) 0.0069(9) C7 0.0389(11) 0.0257(9) 0.0301(11) -0.0003(8) 0.0121(9) 0.0043(8) C8 0.0390(11) 0.0228(10) 0.0354(12) 0.0007(8) 0.0114(9) 0.0056(9) C9 0.0361(11) 0.0300(10) 0.0377(13) 0.0004(7) 0.0069(9) 0.0023(9) C10 0.0344(11) 0.0253(9) 0.0317(11) -0.0005(7) 0.0080(8) -0.0018(8) C11 0.0363(11) 0.0226(9) 0.0356(12) -0.0031(7) 0.0089(9) -0.0027(8) C12 0.0343(11) 0.0264(10) 0.0421(13) -0.0012(7) 0.0099(9) 0.0044(9) C13 0.0410(12) 0.0341(11) 0.0434(13) -0.0030(8) 0.0135(10) 0.0089(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, 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 _geom_angle_publ_flag C1 N1 C8 111.25(14) yes C1 N1 C9 124.33(14) yes C8 N1 C9 121.61(15) yes C10 N2 C11 126.35(15) yes O1 C1 N1 124.56(16) yes O1 C1 C2 128.69(16) yes N1 C1 C2 106.75(15) yes C1 C2 C3 131.21(17) yes C1 C2 C7 107.40(15) yes C3 C2 C7 121.39(17) yes C2 C3 C4 117.35(18) yes C3 C4 C5 121.13(17) yes C4 C5 C6 121.25(18) yes C5 C6 C7 117.03(18) yes C2 C7 C6 121.85(16) yes C2 C7 C8 108.52(15) yes C6 C7 C8 129.61(17) yes O2 C8 N1 124.66(16) yes O2 C8 C7 129.48(17) yes N1 C8 C7 105.85(15) yes N1 C9 C10 108.51(14) yes N1 C9 C13 114.88(18) yes C10 C9 C13 111.12(15) yes O3 C10 N2 120.77(16) yes O3 C10 C9 123.46(15) yes N2 C10 C9 115.70(15) yes O4 C11 N2 119.46(17) yes O4 C11 C12 122.94(17) yes N2 C11 C12 117.59(15) yes C11 C12 C13 114.56(15) yes C9 C13 C12 109.41(18) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.215(2) yes O2 C8 1.212(2) yes O3 C10 1.216(2) yes O4 C11 1.226(2) yes N1 C1 1.395(2) yes N1 C8 1.403(2) yes N1 C9 1.452(2) yes N2 C10 1.378(2) yes N2 C11 1.378(2) yes C1 C2 1.487(2) yes C2 C3 1.372(2) yes C2 C7 1.392(2) yes C3 C4 1.395(2) yes C4 C5 1.388(3) yes C5 C6 1.393(2) yes C6 C7 1.375(2) yes C7 C8 1.486(2) yes C9 C10 1.516(2) yes C9 C13 1.517(3) yes C11 C12 1.500(2) yes C12 C13 1.507(2) yes 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_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N(2) H(2N) O(4) 3_565 2.9061(19) 0.880 2.028 175.1 no