#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202501.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_2202501 loop_ _publ_author_name 'Li, Sheng-Ying' 'Wang, Jian-Feng' 'Zheng, Zhong-Hui' 'Xu, Qing-Yan' 'Huang, Yao-Jian' 'Zhao, Yu-Fen' 'Su, Wen-Jin' _publ_section_title ; 1-(2,4-Dihydroxy-3,5-dimethylphenyl)-ethanone (Clavatol) ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1469 _journal_page_last o1470 _journal_paper_doi 10.1107/S160053680301938X _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C10 H12 O3' _chemical_formula_sum 'C10 H12 O3' _chemical_formula_weight 180.20 _chemical_name_common Clavatol _chemical_name_systematic ; 1-(2,4-Dihydroxy-3,5-dimethyl-phenyl)-ethanone ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _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 96.896(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.3180(10) _cell_length_b 15.200(3) _cell_length_c 7.2040(10) _cell_measurement_reflns_used 3017 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.0 _cell_measurement_theta_min 2.4 _cell_volume 904.2(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_molecular_graphics 'ORTEPIII (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.930 _diffrn_measurement_device_type 'Bruker APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _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 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 5370 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.25 _diffrn_reflns_theta_min 2.47 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.221 _refine_diff_density_min -0.244 _refine_ls_extinction_coef 0.034(8) _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 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 125 _refine_ls_number_reflns 2078 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0515 _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^)+(0.0945P)^2^+0.1420P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1481 _refine_ls_wR_factor_ref 0.1554 _reflns_number_gt 1725 _reflns_number_total 2078 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file ci6269.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2202501 _cod_database_fobs_code 2202501 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 O1 0.69574(13) 0.24726(7) 0.17498(18) 0.0609(4) Uani d . 1 . . O O2 0.51388(12) 0.37873(7) 0.08559(18) 0.0591(4) Uani d . 1 . . O O3 -0.01831(11) 0.32842(7) -0.17279(16) 0.0559(3) Uani d . 1 . . O C1 0.42724(15) 0.22866(9) 0.04071(18) 0.0397(3) Uani d . 1 . . C C2 0.39759(14) 0.31959(9) 0.02716(18) 0.0406(3) Uani d . 1 . . C C3 0.24782(15) 0.35241(9) -0.04823(18) 0.0418(3) Uani d . 1 . . C C4 0.12568(14) 0.29264(10) -0.10492(18) 0.0396(3) Uani d . 1 . . C C5 0.14846(15) 0.20111(9) -0.09173(17) 0.0403(3) Uani d . 1 . . C C6 0.29907(15) 0.17190(9) -0.02101(18) 0.0418(3) Uani d . 1 . . C C7 0.58499(15) 0.19577(10) 0.11649(19) 0.0460(4) Uani d . 1 . . C C8 0.61857(19) 0.09957(12) 0.1245(3) 0.0632(5) Uani d . 1 . . C C9 0.2196(2) 0.44927(11) -0.0692(3) 0.0629(5) Uani d . 1 . . C C10 0.01309(18) 0.13858(11) -0.1530(2) 0.0538(4) Uani d . 1 . . C H2 0.5968 0.3527 0.1273 0.089 Uiso calc R 1 . . H H3 -0.0826 0.2891 -0.2071 0.084 Uiso calc R 1 . . H H6 0.3172 0.1116 -0.0136 0.063 Uiso calc R 1 . . H H8A 0.7302 0.0899 0.1713 0.095 Uiso calc R 1 . . H H8B 0.5966 0.0749 0.0014 0.095 Uiso calc R 1 . . H H8C 0.5506 0.0719 0.2061 0.095 Uiso calc R 1 . . H H9A 0.1592 0.4611 -0.1887 0.094 Uiso calc R 1 . . H H9B 0.3219 0.4792 -0.0608 0.094 Uiso calc R 1 . . H H9C 0.1598 0.4697 0.0282 0.094 Uiso calc R 1 . . H H10A 0.0507 0.0792 -0.1338 0.081 Uiso calc R 1 . . H H10B -0.0231 0.1476 -0.2832 0.081 Uiso calc R 1 . . H H10C -0.0751 0.1489 -0.0811 0.081 Uiso calc R 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 O1 0.0290(5) 0.0665(7) 0.0808(8) -0.0049(4) -0.0191(5) 0.0076(6) O2 0.0332(6) 0.0524(6) 0.0862(8) -0.0120(4) -0.0159(5) 0.0016(5) O3 0.0268(5) 0.0630(7) 0.0733(7) 0.0035(4) -0.0130(4) -0.0029(5) C1 0.0264(6) 0.0510(7) 0.0395(7) -0.0041(5) -0.0053(5) 0.0043(5) C2 0.0268(6) 0.0499(8) 0.0432(7) -0.0080(5) -0.0042(5) 0.0007(5) C3 0.0295(6) 0.0479(7) 0.0464(7) -0.0021(5) -0.0022(5) -0.0009(5) C4 0.0240(6) 0.0546(8) 0.0384(6) -0.0009(5) -0.0032(4) -0.0015(5) C5 0.0281(6) 0.0528(8) 0.0383(6) -0.0070(5) -0.0031(5) -0.0013(5) C6 0.0314(6) 0.0470(7) 0.0447(7) -0.0046(5) -0.0047(5) 0.0022(5) C7 0.0278(6) 0.0589(8) 0.0485(7) -0.0029(6) -0.0064(5) 0.0086(6) C8 0.0394(8) 0.0595(10) 0.0862(12) 0.0038(7) -0.0112(7) 0.0134(8) C9 0.0422(8) 0.0495(8) 0.0934(13) 0.0006(6) -0.0067(8) -0.0017(8) C10 0.0342(7) 0.0587(9) 0.0648(9) -0.0115(6) -0.0087(6) -0.0035(7) 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 _geom_angle_publ_flag C2 O2 H2 109.5 yes C4 O3 H3 109.5 yes C6 C1 C2 117.60(10) yes C6 C1 C7 121.80(10) yes C2 C1 C7 120.60(10) yes O2 C2 C3 117.20(10) yes O2 C2 C1 121.30(10) yes C3 C2 C1 121.40(10) yes C4 C3 C2 118.10(10) yes C4 C3 C9 121.00(10) yes C2 C3 C9 121.00(10) yes O3 C4 C3 115.40(10) yes O3 C4 C5 121.90(10) yes C3 C4 C5 122.70(10) yes C6 C5 C4 117.10(10) yes C6 C5 C10 121.70(10) yes C4 C5 C10 121.20(10) yes C5 C6 C1 123.10(10) yes O1 C7 C1 120.80(10) yes O1 C7 C8 118.50(10) yes C1 C7 C8 120.70(10) yes C5 C6 H6 118.5 no C1 C6 H6 118.5 no C7 C8 H8A 109.5 no C7 C8 H8B 109.5 no H8A C8 H8B 109.5 no C7 C8 H8C 109.5 no H8A C8 H8C 109.5 no H8B C8 H8C 109.5 no C3 C9 H9A 109.5 no C3 C9 H9B 109.5 no H9A C9 H9B 109.5 no C3 C9 H9C 109.5 no H9A C9 H9C 109.5 no H9B C9 H9C 109.5 no C5 C10 H10A 109.5 no C5 C10 H10B 109.5 no C5 C10 H10C 109.5 no H10A C10 H10B 109.5 no H10A C10 H10C 109.5 no H10B C10 H10C 109.5 no 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 O1 C7 . 1.243(2) yes O2 C2 . 1.350(2) yes O3 C4 . 1.352(2) yes C1 C6 . 1.402(2) yes C1 C2 . 1.405(2) yes C1 C7 . 1.448(2) yes C2 C3 . 1.390(2) yes C3 C4 . 1.387(2) yes C3 C9 . 1.496(2) yes C4 C5 . 1.406(2) yes C5 C6 . 1.369(2) yes C5 C10 . 1.499(2) yes C7 C8 . 1.489(2) yes O2 H2 . 0.82 no O3 H3 . 0.82 no C6 H6 . 0.93 no C8 H8A . 0.96 no C8 H8B . 0.96 no C8 H8C . 0.96 no C9 H9A . 0.96 no C9 H9B . 0.96 no C9 H9C . 0.96 no C10 H10A . 0.96 no C10 H10B . 0.96 no C10 H10C . 0.96 no 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 O2 H2 O1 . 0.82 1.82 2.542(2) 147 yes O3 H3 O1 4_465 0.82 2.01 2.7490(10) 149 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 _geom_torsion_publ_flag C6 C1 C2 O2 179.19(12) no C7 C1 C2 O2 -0.6(2) no C6 C1 C2 C3 -1.3(2) no C7 C1 C2 C3 178.85(12) no O2 C2 C3 C4 -178.50(12) no C1 C2 C3 C4 2.0(2) no O2 C2 C3 C9 2.1(2) no C1 C2 C3 C9 -177.45(14) no C2 C3 C4 O3 178.44(12) no C9 C3 C4 O3 -2.1(2) no C2 C3 C4 C5 -1.0(2) no C9 C3 C4 C5 178.42(14) no O3 C4 C5 C6 179.99(12) no C3 C4 C5 C6 -0.6(2) no O3 C4 C5 C10 0.1(2) no C3 C4 C5 C10 179.48(13) no C4 C5 C6 C1 1.3(2) no C2 C1 C6 C5 -0.4(2) no C7 C1 C6 C5 179.43(12) no C6 C1 C7 O1 -178.10(13) no C2 C1 C7 O1 1.7(2) yes C6 C1 C7 C8 2.5(2) yes C2 C1 C7 C8 -177.72(14) no C10 C5 C6 C1 -178.76(13) no