#------------------------------------------------------------------------------ #$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/60/2106008.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_2106008 loop_ _publ_author_name 'Zhang, Qi' 'Li, Meiqi' 'Mei, Xuefeng' _publ_section_title ; A new polymorph of 1-hydroxy-2-naphthoic acid obtained during failed co-crystallization experiments ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first ; ; _journal_paper_doi 10.1107/S2052520614026134 _journal_volume 71 _journal_year 2015 _chemical_formula_moiety 'C11 H8 O3' _chemical_formula_sum 'C11 H8 O3' _chemical_formula_weight 188.17 _chemical_name_common HNA _chemical_name_systematic ; ? ; _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' _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 125.339(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 20.920(5) _cell_length_b 6.9926(14) _cell_length_c 14.688(3) _cell_measurement_reflns_used 2087 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.44 _cell_measurement_theta_min 2.39 _cell_volume 1752.7(7) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _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 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 7678 _diffrn_reflns_theta_full 27.54 _diffrn_reflns_theta_max 27.54 _diffrn_reflns_theta_min 2.39 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_description columnar _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.489 _refine_diff_density_min -0.273 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 133 _refine_ls_number_reflns 2015 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0683 _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^)+(0.1338P)^2^+0.4921P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1902 _refine_ls_wR_factor_ref 0.2263 _reflns_number_gt 1239 _reflns_number_total 2015 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL mo_2014375_0m in C2/c CELL 0.71073 20.9202 6.9926 14.6879 90.000 125.339 90.000 ZERR 8.00 0.0047 0.0014 0.0031 0.000 0.010 0.000 LATT 7 SYMM -x, y, -z+1/2 SFAC C H O UNIT 88 64 24 L.S. 10 ACTA BOND $H FMAP 2 PLAN 2 HTAB CONF TEMP 23.000 WGHT 0.133800 0.492100 FVAR 0.07004 O3 3 0.512296 0.129699 0.137718 11.00000 0.03214 0.09179 = 0.04244 -0.00182 0.02306 0.00119 H2 2 0.474111 0.137414 0.151606 11.00000 -1.50000 O2 3 0.596605 0.136383 0.323386 11.00000 0.03486 0.07391 = 0.03936 -0.00032 0.02503 -0.00158 O1 3 0.746614 0.140422 0.410352 11.00000 0.03599 0.07181 = 0.03318 -0.00142 0.02093 -0.00187 H1 2 0.704384 0.140157 0.407964 11.00000 -1.50000 C11 1 0.584351 0.131698 0.229906 11.00000 0.03105 0.04445 = 0.03922 -0.00124 0.02190 -0.00107 C2 1 0.646019 0.128138 0.212695 11.00000 0.03220 0.03813 = 0.03647 0.00008 0.02111 -0.00029 C1 1 0.723984 0.132882 0.304340 11.00000 0.03568 0.03672 = 0.03432 -0.00146 0.02242 -0.00091 C10 1 0.785553 0.129528 0.288294 11.00000 0.03669 0.03054 = 0.04668 -0.00010 0.02772 -0.00044 C9 1 0.864988 0.132777 0.379651 11.00000 0.03675 0.04726 = 0.05425 -0.00404 0.02572 -0.00375 AFIX 43 H8 2 0.878664 0.136388 0.452185 11.00000 -1.20000 AFIX 0 C8 1 0.921898 0.130582 0.360940 11.00000 0.03509 0.05759 = 0.08083 -0.00551 0.03166 -0.00661 AFIX 43 H7 2 0.974385 0.134648 0.421106 11.00000 -1.20000 AFIX 0 C7 1 0.902079 0.122353 0.253109 11.00000 0.05072 0.06266 = 0.09394 -0.00717 0.05600 -0.00701 AFIX 43 H6 2 0.941650 0.119339 0.242198 11.00000 -1.20000 AFIX 0 C6 1 0.825534 0.118581 0.162496 11.00000 0.06239 0.05283 = 0.07004 -0.00170 0.05313 -0.00178 AFIX 43 H5 2 0.813358 0.114071 0.090786 11.00000 -1.20000 AFIX 0 C5 1 0.764832 0.121577 0.178385 11.00000 0.04492 0.03539 = 0.05094 -0.00236 0.03478 -0.00331 C4 1 0.684473 0.116979 0.086434 11.00000 0.05193 0.05464 = 0.03926 -0.00033 0.03171 0.00171 AFIX 43 H4 2 0.671123 0.112540 0.014084 11.00000 -1.20000 AFIX 0 C3 1 0.627559 0.118980 0.102992 11.00000 0.03525 0.05133 = 0.03311 -0.00100 0.01851 -0.00011 AFIX 43 H3 2 0.575380 0.114312 0.041874 11.00000 -1.20000 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM mo_2014375_0m in C2/c REM R1 = 0.0683 for 1239 Fo > 4sig(Fo) and 0.1018 for all 2015 data REM 133 parameters refined using 0 restraints END WGHT 0.1367 0.4777 REM Highest difference peak 0.489, deepest hole -0.273, 1-sigma level 0.074 Q1 1 0.7510 0.0746 0.0888 11.00000 0.05 0.49 Q2 1 0.9019 0.0685 0.1738 11.00000 0.05 0.46 ; _cod_data_source_file ry5063sup1.cif _cod_data_source_block mo_II _cod_original_cell_volume 1752.7(6) _cod_original_sg_symbol_H-M C2/c _cod_database_code 2106008 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_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 _atom_site_symmetry_multiplicity O O3 0.51230(9) 0.1297(2) 0.13772(13) 0.0546(5) Uani d . 1 1 H H2 0.474(2) 0.137(3) 0.152(2) 0.082 Uiso d . 1 1 O O2 0.59661(9) 0.1364(2) 0.32339(13) 0.0473(5) Uani d . 1 1 O O1 0.74661(9) 0.1404(2) 0.41035(12) 0.0465(5) Uani d . 1 1 H H1 0.704(2) 0.140(3) 0.408(2) 0.070 Uiso d . 1 1 C C11 0.58435(12) 0.1317(3) 0.22991(17) 0.0373(5) Uani d . 1 1 C C2 0.64602(12) 0.1281(2) 0.21269(17) 0.0349(5) Uani d . 1 1 C C1 0.72398(12) 0.1329(2) 0.30434(17) 0.0343(5) Uani d . 1 1 C C10 0.78555(12) 0.1295(2) 0.28829(17) 0.0359(5) Uani d . 1 1 C C9 0.86499(13) 0.1328(3) 0.3797(2) 0.0464(6) Uani d . 1 1 H H8 0.8787 0.1364 0.4522 0.056 Uiso calc R 1 1 C C8 0.92190(15) 0.1306(3) 0.3609(3) 0.0589(7) Uani d . 1 1 H H7 0.9744 0.1346 0.4211 0.071 Uiso calc R 1 1 C C7 0.90208(15) 0.1224(3) 0.2531(3) 0.0609(8) Uani d . 1 1 H H6 0.9416 0.1193 0.2422 0.073 Uiso calc R 1 1 C C6 0.82553(15) 0.1186(3) 0.1625(2) 0.0532(6) Uani d . 1 1 H H5 0.8134 0.1141 0.0908 0.064 Uiso calc R 1 1 C C5 0.76483(13) 0.1216(2) 0.17838(18) 0.0397(5) Uani d . 1 1 C C4 0.68447(14) 0.1170(3) 0.08643(18) 0.0455(6) Uani d . 1 1 H H4 0.6711 0.1125 0.0141 0.055 Uiso calc R 1 1 C C3 0.62756(12) 0.1190(3) 0.10299(17) 0.0406(5) Uani d . 1 1 H H3 0.5754 0.1143 0.0419 0.049 Uiso calc R 1 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 O3 0.0321(9) 0.0918(13) 0.0424(9) 0.0012(7) 0.0231(8) -0.0018(7) O2 0.0349(8) 0.0739(11) 0.0394(8) -0.0016(6) 0.0250(7) -0.0003(6) O1 0.0360(8) 0.0718(11) 0.0332(8) -0.0019(7) 0.0209(7) -0.0014(6) C11 0.0310(10) 0.0445(11) 0.0392(11) -0.0011(8) 0.0219(9) -0.0012(8) C2 0.0322(11) 0.0381(10) 0.0365(11) -0.0003(7) 0.0211(9) 0.0001(7) C1 0.0357(11) 0.0367(10) 0.0343(10) -0.0009(8) 0.0224(9) -0.0015(7) C10 0.0367(11) 0.0305(10) 0.0467(12) -0.0004(7) 0.0277(10) -0.0001(7) C9 0.0367(12) 0.0473(12) 0.0543(13) -0.0038(9) 0.0257(11) -0.0040(9) C8 0.0351(13) 0.0576(14) 0.0808(19) -0.0066(10) 0.0317(13) -0.0055(12) C7 0.0507(16) 0.0627(15) 0.094(2) -0.0070(11) 0.0560(16) -0.0072(13) C6 0.0624(16) 0.0528(13) 0.0700(15) -0.0018(10) 0.0531(14) -0.0017(10) C5 0.0449(12) 0.0354(10) 0.0509(13) -0.0033(8) 0.0348(11) -0.0024(8) C4 0.0519(13) 0.0546(13) 0.0393(11) 0.0017(9) 0.0317(11) -0.0003(9) C3 0.0352(11) 0.0513(12) 0.0331(10) -0.0001(8) 0.0185(9) -0.0010(8) 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 C11 O3 H2 112.9(19) C1 O1 H1 107(2) O2 C11 O3 121.11(18) O2 C11 C2 123.83(18) O3 C11 C2 115.06(18) C1 C2 C3 119.65(18) C1 C2 C11 119.61(18) C3 C2 C11 120.73(18) O1 C1 C2 123.61(19) O1 C1 C10 116.29(18) C2 C1 C10 120.10(19) C9 C10 C5 120.23(19) C9 C10 C1 121.3(2) C5 C10 C1 118.50(19) C8 C9 C10 119.5(2) C8 C9 H8 120.2 C10 C9 H8 120.2 C9 C8 C7 120.6(2) C9 C8 H7 119.7 C7 C8 H7 119.7 C6 C7 C8 121.4(2) C6 C7 H6 119.3 C8 C7 H6 119.3 C7 C6 C5 119.7(2) C7 C6 H5 120.1 C5 C6 H5 120.1 C10 C5 C6 118.5(2) C10 C5 C4 119.98(18) C6 C5 C4 121.5(2) C3 C4 C5 120.7(2) C3 C4 H4 119.6 C5 C4 H4 119.6 C4 C3 C2 121.0(2) C4 C3 H3 119.5 C2 C3 H3 119.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O3 C11 1.321(3) O3 H2 0.93(4) O2 C11 1.243(2) O1 C1 1.341(2) O1 H1 0.86(3) C11 C2 1.451(3) C2 C1 1.391(3) C2 C3 1.425(3) C1 C10 1.437(3) C10 C9 1.408(3) C10 C5 1.410(3) C9 C8 1.368(3) C9 H8 0.9300 C8 C7 1.387(4) C8 H7 0.9300 C7 C6 1.368(4) C7 H6 0.9300 C6 C5 1.418(3) C6 H5 0.9300 C5 C4 1.423(3) C4 C3 1.346(3) C4 H4 0.9300 C3 H3 0.9300 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 O2 C11 C2 C1 -1.0(3) O3 C11 C2 C1 179.00(15) O2 C11 C2 C3 178.75(16) O3 C11 C2 C3 -1.3(2) C3 C2 C1 O1 -179.61(15) C11 C2 C1 O1 0.1(3) C3 C2 C1 C10 0.3(2) C11 C2 C1 C10 -179.97(15) O1 C1 C10 C9 0.4(2) C2 C1 C10 C9 -179.53(15) O1 C1 C10 C5 179.99(14) C2 C1 C10 C5 0.1(2) C5 C10 C9 C8 0.8(3) C1 C10 C9 C8 -179.61(16) C10 C9 C8 C7 -1.0(3) C9 C8 C7 C6 0.8(3) C8 C7 C6 C5 -0.5(3) C9 C10 C5 C6 -0.5(2) C1 C10 C5 C6 179.90(16) C9 C10 C5 C4 179.56(16) C1 C10 C5 C4 0.0(2) C7 C6 C5 C10 0.4(3) C7 C6 C5 C4 -179.72(18) C10 C5 C4 C3 -0.4(3) C6 C5 C4 C3 179.68(18) C5 C4 C3 C2 0.8(3) C1 C2 C3 C4 -0.7(3) C11 C2 C3 C4 179.53(17)