#------------------------------------------------------------------------------ #$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176787 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/05/2210539.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_2210539 loop_ _publ_author_name 'Liang, Zu-Pei' 'Li, Jian' _publ_section_title ; 2-(4-Hydroxyphenyl)isoindoline-1,3-dione ; _journal_coeditor_code CI2156 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o4436 _journal_page_last o4437 _journal_paper_doi 10.1107/S1600536806035963 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C14 H9 N O3' _chemical_formula_moiety 'C14 H9 N O3' _chemical_formula_sum 'C14 H9 N O3' _chemical_formula_weight 239.22 _chemical_name_systematic ; 2-(4-hydroxyphenyl)isoindoline-1,3-dione ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 11.524(3) _cell_length_b 7.7133(19) _cell_length_c 24.890(6) _cell_measurement_reflns_used 1804 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 23.42 _cell_measurement_theta_min 2.41 _cell_volume 2212.4(10) _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _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 0.0733 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 11576 _diffrn_reflns_theta_full 26.38 _diffrn_reflns_theta_max 26.38 _diffrn_reflns_theta_min 1.64 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_correction_T_min 0.9679 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.194 _refine_diff_density_min -0.161 _refine_ls_extinction_coef 0.031(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2265 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.918 _refine_ls_R_factor_all 0.0981 _refine_ls_R_factor_gt 0.0426 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0843P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1069 _refine_ls_wR_factor_ref 0.1404 _reflns_number_gt 1300 _reflns_number_total 2265 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci2156.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2210539 _cod_database_fobs_code 2210539 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-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 O1 0.77183(15) -0.0250(2) 0.58590(6) 0.0590(5) Uani d . 1 O O2 0.44736(14) 0.3092(2) 0.60449(6) 0.0530(5) Uani d . 1 O O3 0.66570(16) 0.0333(2) 0.82916(6) 0.0594(6) Uani d . 1 H H3 0.6211 -0.0403 0.8409 0.089 Uiso calc R 1 N N1 0.60792(15) 0.1299(2) 0.60963(7) 0.0350(5) Uani d . 1 C C1 0.6885(2) 0.0607(3) 0.57329(8) 0.0376(6) Uani d . 1 C C2 0.64933(18) 0.1141(3) 0.51912(8) 0.0342(5) Uani d . 1 C C3 0.6961(2) 0.0796(3) 0.46923(9) 0.0435(6) Uani d . 1 H H3A 0.7620 0.0111 0.4656 0.052 Uiso calc R 1 C C4 0.6416(2) 0.1502(3) 0.42493(9) 0.0470(6) Uani d . 1 H H4 0.6718 0.1302 0.3908 0.056 Uiso calc R 1 C C5 0.5424(2) 0.2506(3) 0.43065(9) 0.0467(6) Uani d . 1 H H5 0.5070 0.2971 0.4003 0.056 Uiso calc R 1 C C6 0.49514(19) 0.2827(3) 0.48108(9) 0.0425(6) Uani d . 1 H H6 0.4280 0.3484 0.4850 0.051 Uiso calc R 1 C C7 0.55114(18) 0.2139(3) 0.52476(8) 0.0344(5) Uani d . 1 C C8 0.52461(19) 0.2288(3) 0.58295(9) 0.0358(5) Uani d . 1 C C9 0.61755(19) 0.1118(3) 0.66682(8) 0.0348(5) Uani d . 1 C C10 0.53462(19) 0.0211(3) 0.69535(8) 0.0428(6) Uani d . 1 H H10 0.4697 -0.0226 0.6778 0.051 Uiso calc R 1 C C11 0.54767(19) -0.0049(3) 0.74989(9) 0.0451(6) Uani d . 1 H H11 0.4914 -0.0653 0.7690 0.054 Uiso calc R 1 C C12 0.6442(2) 0.0587(3) 0.77598(8) 0.0389(6) Uani d . 1 C C13 0.7264(2) 0.1509(3) 0.74748(9) 0.0473(6) Uani d . 1 H H13 0.7915 0.1945 0.7650 0.057 Uiso calc R 1 C C14 0.7123(2) 0.1786(3) 0.69306(9) 0.0437(6) Uani d . 1 H H14 0.7670 0.2427 0.6741 0.052 Uiso calc R 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 O1 0.0622(12) 0.0709(12) 0.0440(10) 0.0317(10) 0.0023(8) 0.0036(9) O2 0.0504(10) 0.0678(11) 0.0409(10) 0.0186(9) 0.0068(8) -0.0083(8) O3 0.0751(14) 0.0742(13) 0.0289(10) -0.0172(10) -0.0007(8) 0.0091(8) N1 0.0414(11) 0.0375(10) 0.0259(10) 0.0033(8) 0.0025(8) 0.0012(8) C1 0.0425(13) 0.0354(12) 0.0351(13) 0.0054(10) 0.0043(10) -0.0006(10) C2 0.0385(12) 0.0346(12) 0.0296(12) -0.0016(10) 0.0025(9) -0.0006(9) C3 0.0433(14) 0.0476(14) 0.0398(14) 0.0007(11) 0.0053(11) -0.0086(11) C4 0.0512(15) 0.0607(16) 0.0290(13) -0.0122(13) 0.0047(11) -0.0051(11) C5 0.0571(17) 0.0514(15) 0.0315(14) -0.0090(12) -0.0068(11) 0.0033(11) C6 0.0417(13) 0.0461(14) 0.0398(14) 0.0011(11) -0.0021(11) -0.0027(11) C7 0.0382(12) 0.0352(12) 0.0299(12) -0.0039(10) 0.0005(9) -0.0023(10) C8 0.0396(13) 0.0347(12) 0.0329(12) -0.0012(10) 0.0031(10) -0.0028(10) C9 0.0442(13) 0.0338(12) 0.0265(12) 0.0002(10) 0.0028(10) 0.0015(9) C10 0.0396(14) 0.0542(15) 0.0347(13) -0.0090(11) 0.0007(10) 0.0005(11) C11 0.0438(14) 0.0549(15) 0.0365(14) -0.0087(11) 0.0109(11) 0.0052(11) C12 0.0525(15) 0.0382(12) 0.0258(12) -0.0010(11) 0.0028(10) 0.0036(10) C13 0.0568(15) 0.0492(14) 0.0360(14) -0.0154(12) -0.0056(11) 0.0033(11) C14 0.0501(14) 0.0474(14) 0.0337(14) -0.0116(12) 0.0036(11) 0.0085(11) 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' N N 0.0061 0.0033 '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 C12 O3 H3 109.5 C8 N1 C1 110.94(18) C8 N1 C9 125.40(18) C1 N1 C9 123.47(18) O1 C1 N1 124.6(2) O1 C1 C2 129.2(2) N1 C1 C2 106.22(18) C7 C2 C3 121.4(2) C7 C2 C1 108.28(17) C3 C2 C1 130.3(2) C2 C3 C4 117.8(2) C2 C3 H3A 121.1 C4 C3 H3A 121.1 C3 C4 C5 120.8(2) C3 C4 H4 119.6 C5 C4 H4 119.6 C4 C5 C6 120.9(2) C4 C5 H5 119.5 C6 C5 H5 119.5 C7 C6 C5 117.6(2) C7 C6 H6 121.2 C5 C6 H6 121.2 C6 C7 C2 121.5(2) C6 C7 C8 130.3(2) C2 C7 C8 108.20(18) O2 C8 N1 125.2(2) O2 C8 C7 128.6(2) N1 C8 C7 106.27(18) C14 C9 C10 119.7(2) C14 C9 N1 119.81(19) C10 C9 N1 120.4(2) C11 C10 C9 120.3(2) C11 C10 H10 119.9 C9 C10 H10 119.9 C12 C11 C10 119.9(2) C12 C11 H11 120.0 C10 C11 H11 120.0 O3 C12 C11 123.6(2) O3 C12 C13 116.7(2) C11 C12 C13 119.7(2) C12 C13 C14 120.2(2) C12 C13 H13 119.9 C14 C13 H13 119.9 C9 C14 C13 120.2(2) C9 C14 H14 119.9 C13 C14 H14 119.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.207(3) O2 C8 1.210(2) O3 C12 1.361(2) O3 H3 0.82 N1 C8 1.394(3) N1 C1 1.402(3) N1 C9 1.435(3) C1 C2 1.480(3) C2 C7 1.376(3) C2 C3 1.379(3) C3 C4 1.381(3) C3 H3A 0.93 C4 C5 1.389(3) C4 H4 0.93 C5 C6 1.390(3) C5 H5 0.93 C6 C7 1.371(3) C6 H6 0.93 C7 C8 1.485(3) C9 C14 1.372(3) C9 C10 1.381(3) C10 C11 1.381(3) C10 H10 0.93 C11 C12 1.379(3) C11 H11 0.93 C12 C13 1.380(3) C13 C14 1.381(3) C13 H13 0.93 C14 H14 0.93 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 O3 H3 O2 3_646 0.82 1.95 2.723(2) 156 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 C8 N1 C1 O1 177.4(2) C9 N1 C1 O1 2.2(3) C8 N1 C1 C2 -2.7(2) C9 N1 C1 C2 -177.85(18) O1 C1 C2 C7 -178.8(2) N1 C1 C2 C7 1.3(2) O1 C1 C2 C3 0.7(4) N1 C1 C2 C3 -179.2(2) C7 C2 C3 C4 0.7(3) C1 C2 C3 C4 -178.7(2) C2 C3 C4 C5 -0.8(3) C3 C4 C5 C6 -0.1(4) C4 C5 C6 C7 1.0(3) C5 C6 C7 C2 -1.1(3) C5 C6 C7 C8 178.1(2) C3 C2 C7 C6 0.3(3) C1 C2 C7 C6 179.82(19) C3 C2 C7 C8 -179.08(19) C1 C2 C7 C8 0.4(2) C1 N1 C8 O2 -177.0(2) C9 N1 C8 O2 -2.0(3) C1 N1 C8 C7 3.0(2) C9 N1 C8 C7 177.99(18) C6 C7 C8 O2 -1.4(4) C2 C7 C8 O2 177.9(2) C6 C7 C8 N1 178.6(2) C2 C7 C8 N1 -2.1(2) C8 N1 C9 C14 -113.4(2) C1 N1 C9 C14 61.0(3) C8 N1 C9 C10 69.3(3) C1 N1 C9 C10 -116.2(2) C14 C9 C10 C11 -1.1(3) N1 C9 C10 C11 176.2(2) C9 C10 C11 C12 -0.4(4) C10 C11 C12 O3 -177.5(2) C10 C11 C12 C13 1.2(4) O3 C12 C13 C14 178.4(2) C11 C12 C13 C14 -0.3(4) C10 C9 C14 C13 1.9(4) N1 C9 C14 C13 -175.3(2) C12 C13 C14 C9 -1.2(4)