#------------------------------------------------------------------------------ #$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $ #$Revision: 14 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203256.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_2203256 loop_ _publ_author_name 'Twamley, Brendan' 'Zawadzka, Anna' 'Paszczynski, Andrzej J.' _publ_section_title ; 8-Hydroxy-3,4-dimethylisocoumarin ; _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o370 _journal_page_last o371 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C11 H10 O3' _chemical_formula_moiety 'C11 H10 O3' _chemical_formula_sum 'C11 H10 O3' _chemical_formula_weight 190.19 _chemical_melting_point 129\% _chemical_name_systematic ; 8-hydroxy-3,4-dimethylisocoumarin ; _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 102.56(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 11.283(2) _cell_length_b 15.457(3) _cell_length_c 10.365(2) _cell_measurement_reflns_used 356 _cell_measurement_temperature 81(2) _cell_measurement_theta_max 19.08 _cell_measurement_theta_min 2.27 _cell_volume 1764.3(6) _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_collection 'SMART (Bruker 2001)' _computing_data_reduction SAINT-Plus _computing_molecular_graphics 'XP in SHELXTL' _computing_publication_material 'XCIF in SHELXTL' _computing_structure_refinement 'XL in SHELXTL' _computing_structure_solution 'XS in SHELXTL (Sheldrick, 1998)' _diffrn_ambient_temperature 81(2) _diffrn_detector_area_resol_mean 8.3 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker--Siemens SMART APEX' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1160 _diffrn_reflns_av_sigmaI/netI 0.0887 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 10791 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_min 2.27 _diffrn_standards_decay_% <0.01 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_number ? _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_correction_T_min 0.9845 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.232 _refine_diff_density_min -0.215 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 133 _refine_ls_number_reflns 1650 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.1078 _refine_ls_R_factor_gt 0.0596 _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^)+(0.0349P)^2^+1.8671P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1116 _refine_ls_wR_factor_ref 0.1282 _reflns_number_gt 1057 _reflns_number_total 1650 _reflns_threshold_expression I>2\s(I) 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 C3 0.9093(3) 0.3023(2) 0.0853(3) 0.0173(7) Uani d . 1 . . C C4 0.9203(3) 0.2207(2) 0.0474(3) 0.0169(7) Uani d . 1 . . C C4A 0.8709(3) 0.15051(18) 0.1137(3) 0.0152(7) Uani d . 1 . . C C5 0.8783(3) 0.06358(19) 0.0798(3) 0.0197(7) Uani d . 1 . . C H5 0.9180 0.0478 0.0114 0.024 Uiso calc R 1 . . H C6 0.8278(3) 0.0004(2) 0.1458(3) 0.0222(8) Uani d . 1 . . C H6 0.8330 -0.0584 0.1212 0.027 Uiso calc R 1 . . H C7 0.7699(3) 0.02065(19) 0.2468(3) 0.0202(7) Uani d . 1 . . C H7 0.7354 -0.0238 0.2902 0.024 Uiso calc R 1 . . H C8 0.7626(3) 0.10597(18) 0.2838(3) 0.0172(7) Uani d . 1 . . C C8A 0.8132(2) 0.17165(19) 0.2177(3) 0.0140(7) Uani d . 1 . . C C1 0.8051(3) 0.26053(18) 0.2567(3) 0.0145(7) Uani d . 1 . . C C31 0.9535(3) 0.38462(19) 0.0372(3) 0.0236(8) Uani d . 1 . . C H31A 0.9918 0.3723 -0.0371 0.035 Uiso calc R 1 . . H H31B 1.0130 0.4116 0.1089 0.035 Uiso calc R 1 . . H H31C 0.8849 0.4240 0.0082 0.035 Uiso calc R 1 . . H C41 0.9829(3) 0.1990(2) -0.0639(3) 0.0233(8) Uani d . 1 . . C H41A 1.0012 0.2525 -0.1063 0.035 Uiso calc R 1 . . H H41B 0.9294 0.1626 -0.1292 0.035 Uiso calc R 1 . . H H41C 1.0585 0.1678 -0.0282 0.035 Uiso calc R 1 . . H O2 0.85064(17) 0.32194(12) 0.18753(18) 0.0168(5) Uani d . 1 . . O O1 0.75960(18) 0.28611(13) 0.34692(19) 0.0195(5) Uani d . 1 . . O O8 0.70482(19) 0.12384(15) 0.3825(2) 0.0219(5) Uani d . 1 . . O H8 0.711(3) 0.183(3) 0.396(4) 0.058(13) Uiso d . 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 C3 0.0139(16) 0.0251(18) 0.0129(16) 0.0017(13) 0.0034(13) 0.0043(13) C4 0.0150(16) 0.0207(17) 0.0143(16) 0.0031(13) 0.0017(13) 0.0019(14) C4A 0.0119(15) 0.0194(16) 0.0119(15) 0.0018(13) -0.0029(12) -0.0022(13) C5 0.0194(17) 0.0209(17) 0.0180(17) 0.0056(14) 0.0023(13) -0.0040(14) C6 0.0259(18) 0.0157(16) 0.0210(18) 0.0031(14) -0.0037(15) -0.0043(14) C7 0.0215(17) 0.0162(17) 0.0205(17) -0.0012(13) -0.0003(14) 0.0044(14) C8 0.0179(16) 0.0177(17) 0.0153(16) -0.0001(13) 0.0021(14) -0.0026(13) C8A 0.0111(15) 0.0173(16) 0.0119(15) -0.0010(13) -0.0012(12) -0.0019(13) C1 0.0114(15) 0.0178(17) 0.0138(16) 0.0009(13) 0.0015(13) 0.0029(13) C31 0.0225(17) 0.0251(18) 0.0221(18) 0.0011(14) 0.0024(14) 0.0053(14) C41 0.0201(17) 0.033(2) 0.0178(17) 0.0024(15) 0.0065(13) -0.0011(15) O2 0.0182(12) 0.0166(12) 0.0166(11) -0.0003(9) 0.0058(9) 0.0016(9) O1 0.0225(12) 0.0194(12) 0.0182(12) 0.0018(9) 0.0079(10) -0.0021(10) O8 0.0275(13) 0.0226(13) 0.0180(12) -0.0029(10) 0.0103(10) -0.0005(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 C3 O2 . . 121.1(3) ? C4 C3 C31 . . 130.4(3) ? O2 C3 C31 . . 108.5(2) ? C3 C4 C4A . . 119.7(2) ? C3 C4 C41 . . 121.4(3) ? C4A C4 C41 . . 118.9(3) ? C5 C4A C8A . . 118.5(3) ? C5 C4A C4 . . 123.2(3) ? C8A C4A C4 . . 118.3(2) ? C6 C5 C4A . . 120.1(3) ? C6 C5 H5 . . 119.9 ? C4A C5 H5 . . 119.9 ? C5 C6 C7 . . 121.8(3) ? C5 C6 H6 . . 119.1 ? C7 C6 H6 . . 119.1 ? C8 C7 C6 . . 119.5(3) ? C8 C7 H7 . . 120.3 ? C6 C7 H7 . . 120.3 ? O8 C8 C7 . . 118.2(3) ? O8 C8 C8A . . 122.1(3) ? C7 C8 C8A . . 119.8(3) ? C8 C8A C4A . . 120.4(3) ? C8 C8A C1 . . 119.5(2) ? C4A C8A C1 . . 120.1(3) ? O1 C1 O2 . . 116.6(3) ? O1 C1 C8A . . 125.7(3) ? O2 C1 C8A . . 117.7(2) ? C3 C31 H31A . . 109.5 ? C3 C31 H31B . . 109.5 ? H31A C31 H31B . . 109.5 ? C3 C31 H31C . . 109.5 ? H31A C31 H31C . . 109.5 ? H31B C31 H31C . . 109.5 ? C4 C41 H41A . . 109.5 ? C4 C41 H41B . . 109.5 ? H41A C41 H41B . . 109.5 ? C4 C41 H41C . . 109.5 ? H41A C41 H41C . . 109.5 ? H41B C41 H41C . . 109.5 ? C1 O2 C3 . . 123.0(2) ? C8 O8 H8 . . 107(2) ? 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 C3 C4 . 1.336(4) ? C3 O2 . 1.399(3) ? C3 C31 . 1.491(4) ? C4 C4A . 1.458(4) ? C4 C41 . 1.516(4) ? C4A C5 . 1.396(4) ? C4A C8A . 1.413(4) ? C5 C6 . 1.384(4) ? C5 H5 . 0.9500 ? C6 C7 . 1.384(4) ? C6 H6 . 0.9500 ? C7 C8 . 1.381(4) ? C7 H7 . 0.9500 ? C8 O8 . 1.356(3) ? C8 C8A . 1.413(4) ? C8A C1 . 1.440(4) ? C1 O1 . 1.226(3) ? C1 O2 . 1.356(3) ? C31 H31A . 0.9800 ? C31 H31B . 0.9800 ? C31 H31C . 0.9800 ? C41 H41A . 0.9800 ? C41 H41B . 0.9800 ? C41 H41C . 0.9800 ? O8 H8 . 0.92(4) ? 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 O8 H8 O1 . 0.92(4) 1.80(4) 2.628(3) 148(3)