#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/17/2011742.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_2011742 loop_ _publ_author_name 'Ferreira, Ester S. B.' 'Hulme, Alison N.' 'McNab, Hamish' 'Parsons, Simon' 'Quye, Anita' _publ_section_title ; 2',4',6'-Trihydroxy-1-methoxyacetophenone monohydrate at 150K ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 211 _journal_page_last 212 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C9 H10 O5 , H2 O' _chemical_formula_sum 'C9 H12 O6' _chemical_formula_weight 216.19 _chemical_melting_point 197.5(5) _chemical_name_systematic ; '2',4',6'-trihydroxy-1-methoxyacetophenone' ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 117.8380(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 17.3138(5) _cell_length_b 7.33300(10) _cell_length_c 16.8507(5) _cell_measurement_reflns_used 24172 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.56 _cell_measurement_theta_min 2.66 _cell_volume 1891.81(8) _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full .997 _diffrn_measured_fraction_theta_max .997 _diffrn_measurement_device_type 'Nonius kappa-ccd' _diffrn_measurement_method \w-\f _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0760 _diffrn_reflns_av_sigmaI/netI .0349 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 24172 _diffrn_reflns_theta_full 27.56 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_min 2.66 _diffrn_standards_decay_% ; Correction applied as part of Sortav procedure. ; _exptl_absorpt_coefficient_mu .129 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min .811 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995, 1997)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 912 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .10 _refine_diff_density_max .252 _refine_diff_density_min -.299 _refine_ls_extinction_coef .0031(7) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 185 _refine_ls_number_reflns 2180 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all .0641 _refine_ls_R_factor_gt .0405 _refine_ls_shift/su_max .003 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.0798P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1091 _reflns_number_gt 1594 _reflns_number_total 2180 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bj1012.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _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: '_chemical_melting_point' value '197-198' was changed to '197.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '197-198' was changed to '197.5(5)' - the average value was taken and precision was estimated. '_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. '_geom_hbond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2011742 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 C1 .23569(8) .00284(15) .00971(8) .0180(3) Uani d . 1 . . C C11 .25519(8) .06309(16) .09908(8) .0195(3) Uani d . 1 . . C O11 .19824(6) .05665(13) .12456(6) .0261(3) Uani d . 1 . . O C12 .34383(9) .13446(18) .16560(9) .0208(3) Uani d . 1 . . C H121 .3602(9) .239(2) .1421(9) .024(4) Uiso d . 1 . . H H122 .3880(9) .0317(19) .1771(9) .026(4) Uiso d . 1 . . H O13 .34140(6) .18287(13) .24528(6) .0258(3) Uani d . 1 . . O C14 .42330(10) .2538(2) .31023(10) .0285(4) Uani d . 1 . . C H141 .4389(11) .363(2) .2867(11) .039(4) Uiso d . 1 . . H H142 .4170(11) .280(2) .3634(12) .043(5) Uiso d . 1 . . H H143 .4686(11) .162(2) .3287(10) .037(4) Uiso d . 1 . . H C2 .29487(8) .01225(16) -.02657(8) .0187(3) Uani d . 1 . . C O2 .37443(6) .08560(13) .02463(6) .0243(3) Uani d . 1 . . O H2 .4013(13) .096(3) -.0067(12) .052(6) Uiso d . 1 . . H C3 .27236(9) -.05141(17) -.11188(9) .0203(3) Uani d . 1 . . C H3 .3131(9) -.0447(18) -.1343(9) .019(3) Uiso d . 1 . . H C4 .19037(9) -.12680(16) -.16349(9) .0212(3) Uani d . 1 . . C O4 .16706(7) -.19456(14) -.24634(6) .0301(3) Uani d . 1 . . O H4 .2034(14) -.161(3) -.2648(13) .064(6) Uiso d . 1 . . H C5 .12936(9) -.13642(17) -.13223(9) .0215(3) Uani d . 1 . . C H5 .0720(10) -.1879(18) -.1684(9) .021(4) Uiso d . 1 . . H C6 .15172(8) -.07230(17) -.04718(9) .0196(3) Uani d . 1 . . C O6 .08997(6) -.08119(13) -.01953(7) .0260(3) Uani d . 1 . . O H6 .1135(12) -.035(2) .0366(14) .057(6) Uiso d . 1 . . H O1W .04638(7) .34550(14) .07748(7) .0282(3) Uani d . 1 . . O H1W .0019(13) .275(3) .0575(13) .058(6) Uiso d . 1 . . H H2W .0810(14) .297(3) .1330(16) .064(6) 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 C1 .0200(7) .0173(7) .0184(7) .0011(5) .0104(6) .0022(5) C11 .0220(7) .0173(6) .0217(7) .0015(5) .0125(6) .0032(5) O11 .0248(6) .0348(6) .0246(5) -.0039(4) .0165(5) -.0045(4) C12 .0245(8) .0220(7) .0188(7) -.0005(5) .0124(6) -.0008(5) O13 .0254(6) .0367(6) .0178(5) -.0048(4) .0121(4) -.0063(4) C14 .0280(9) .0347(9) .0206(8) -.0039(6) .0095(7) -.0041(6) C2 .0183(7) .0170(6) .0205(7) .0013(5) .0088(6) .0022(5) O2 .0188(5) .0349(6) .0221(5) -.0048(4) .0118(4) -.0045(4) C3 .0225(7) .0212(7) .0219(7) .0001(5) .0143(6) .0012(5) C4 .0294(8) .0182(7) .0178(7) -.0005(5) .0125(6) .0010(5) O4 .0367(7) .0376(6) .0216(6) -.0122(5) .0183(5) -.0084(4) C5 .0220(8) .0218(7) .0199(7) -.0032(5) .0092(6) .0012(5) C6 .0207(7) .0184(7) .0229(7) .0000(5) .0128(6) .0022(5) O6 .0225(6) .0362(6) .0250(6) -.0074(4) .0157(5) -.0054(4) O1W .0218(6) .0355(6) .0272(6) -.0030(4) .0115(5) .0039(5) 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 C1 C2 . 1.4190(18) ? C1 C6 . 1.4265(18) ? C1 C11 . 1.4499(17) ? C11 O11 . 1.2466(15) ? C11 C12 . 1.5096(18) ? C12 O13 . 1.4084(16) ? C12 H121 . .964(15) ? C12 H122 . 1.025(14) ? O13 C14 . 1.4246(17) ? C14 H141 . .986(16) ? C14 H142 . .972(19) ? C14 H143 . .967(16) ? C2 O2 . 1.3495(15) ? C2 C3 . 1.3831(18) ? O2 H2 . .86(2) ? C3 C4 . 1.3872(19) ? C3 H3 . .945(15) ? C4 O4 . 1.3537(16) ? C4 C5 . 1.3849(19) ? O4 H4 . .86(2) ? C5 C6 . 1.3808(18) ? C5 H5 . .967(14) ? C6 O6 . 1.3527(16) ? O6 H6 . .90(2) ? O1W H1W . .86(2) ? O1W H2W . .92(2) ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C2 C1 C6 116.34(11) C2 C1 C11 124.61(11) C6 C1 C11 119.06(11) O11 C11 C1 120.54(12) O11 C11 C12 116.80(11) C1 C11 C12 122.66(11) O13 C12 C11 108.82(10) O13 C12 H121 109.7(8) C11 C12 H121 111.2(8) O13 C12 H122 110.9(8) C11 C12 H122 107.2(8) H121 C12 H122 109.0(12) C12 O13 C14 111.25(10) O13 C14 H141 110.4(9) O13 C14 H142 106.3(10) H141 C14 H142 112.2(14) O13 C14 H143 111.1(9) H141 C14 H143 111.1(13) H142 C14 H143 105.4(14) O2 C2 C3 120.47(12) O2 C2 C1 118.08(11) C3 C2 C1 121.45(12) C2 O2 H2 109.2(12) C2 C3 C4 119.69(12) C2 C3 H3 119.9(8) C4 C3 H3 120.4(8) O4 C4 C5 117.42(12) O4 C4 C3 121.18(12) C5 C4 C3 121.39(12) C4 O4 H4 110.8(14) C6 C5 C4 118.91(12) C6 C5 H5 119.6(9) C4 C5 H5 121.4(9) O6 C6 C5 117.23(12) O6 C6 C1 120.57(11) C5 C6 C1 122.20(12) C6 O6 H6 107.5(12) H1W O1W H2W 101.7(18) 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 O1W 7_555 .85(2) 1.85(2) 2.7017(16) 171(2) y O4 H4 O11 6_555 .86(3) 1.98(2) 2.6727(15) 137(2) y O4 H4 O13 6_555 .86(3) 2.32(3) 3.0881(17) 149.1(19) y O6 H6 O11 . .90(2) 1.66(2) 2.4860(14) 150(2) y O1W H1W O6 5_555 .86(2) 2.00(2) 2.8514(16) 172(2) y O1W H2W O4 6_556 .92(2) 2.02(2) 2.9345(14) 175(2) y _journal_paper_doi 10.1107/S0108270100018485