#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/43/2014340.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_2014340 loop_ _publ_author_name 'Marciniak, Bernard' 'Rozycka-Sokolowska, Ewa' 'Pavlyuk, Volodymyr' _publ_section_title ; Naphthalene-1,3-diol ; _journal_coeditor_code GD1424 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o68 _journal_page_last o70 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C10 H8 O2' _chemical_formula_moiety 'C10 H8 O2' _chemical_formula_sum 'C10 H8 O2' _chemical_formula_weight 160.16 _chemical_name_common 1,3-dihydroxynaphthalene _chemical_name_systematic ; Naphthalene-1,3-diol ; _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 SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 119.96(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.0606(18) _cell_length_b 7.2027(14) _cell_length_c 13.309(3) _cell_measurement_reflns_used 3650 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.02 _cell_measurement_theta_min 4.60 _cell_volume 752.5(4) _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2002)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED' _computing_molecular_graphics 'PLATON (Spek, 2003) and RPLUTO (Motherwell et al., 2000)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur3 CCD area-detector' _diffrn_measurement_method \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 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 3650 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 4.60 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.127 _refine_diff_density_min -0.160 _refine_ls_extinction_coef 0.065(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 1312 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.171 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0489 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.1818P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1129 _refine_ls_wR_factor_ref 0.1192 _reflns_number_gt 1139 _reflns_number_total 1312 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1424.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2014340 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 C1 0.2499(2) 0.8877(3) 0.23863(15) 0.0407(5) Uani d . 1 . . C C2 0.3512(2) 0.8147(3) 0.20084(16) 0.0450(5) Uani d . 1 . . C H2 0.4690 0.8211 0.2471 0.054 Uiso calc R 1 . . H C3 0.2778(2) 0.7298(3) 0.09212(16) 0.0415(5) Uani d . 1 . . C C4 0.1083(2) 0.7167(3) 0.02371(16) 0.0419(5) Uani d . 1 . . C H4 0.0621 0.6588 -0.0482 0.050 Uiso calc R 1 . . H C5 0.0011(2) 0.7910(2) 0.06155(15) 0.0373(5) Uani d . 1 . . C C6 -0.1773(2) 0.7808(3) -0.00702(18) 0.0474(5) Uani d . 1 . . C H6 -0.2264 0.7235 -0.0792 0.057 Uiso calc R 1 . . H C7 -0.2779(3) 0.8535(3) 0.0310(2) 0.0561(6) Uani d . 1 . . C H7 -0.3956 0.8440 -0.0150 0.067 Uiso calc R 1 . . H C8 -0.2079(3) 0.9427(3) 0.1382(2) 0.0559(6) Uani d . 1 . . C H8 -0.2790 0.9933 0.1628 0.067 Uiso calc R 1 . . H C9 -0.0369(3) 0.9555(3) 0.20647(18) 0.0477(5) Uani d . 1 . . C H9 0.0091 1.0152 0.2778 0.057 Uiso calc R 1 . . H C10 0.0714(2) 0.8792(2) 0.17030(15) 0.0383(5) Uani d . 1 . . C O11 0.3137(2) 0.9713(2) 0.34456(12) 0.0558(5) Uani d . 1 . . O H11 0.409(4) 1.020(5) 0.364(3) 0.105(11) Uiso d . 1 . . H O12 0.38935(19) 0.6626(2) 0.05988(14) 0.0558(5) Uani d . 1 . . O H12 0.334(3) 0.623(4) -0.014(2) 0.081(8) 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 0.0475(11) 0.0424(11) 0.0311(10) -0.0081(9) 0.0187(8) -0.0006(8) C2 0.0371(10) 0.0573(13) 0.0362(10) -0.0014(9) 0.0151(9) 0.0052(9) C3 0.0440(11) 0.0457(11) 0.0380(11) 0.0062(9) 0.0229(9) 0.0058(8) C4 0.0472(11) 0.0401(11) 0.0360(10) -0.0001(8) 0.0191(9) -0.0006(8) C5 0.0416(10) 0.0318(10) 0.0378(10) -0.0015(8) 0.0193(8) 0.0025(8) C6 0.0433(11) 0.0440(11) 0.0478(12) -0.0017(9) 0.0175(9) 0.0013(9) C7 0.0417(11) 0.0543(13) 0.0715(16) 0.0025(9) 0.0276(11) 0.0080(11) C8 0.0595(14) 0.0517(13) 0.0711(15) 0.0107(10) 0.0436(12) 0.0062(11) C9 0.0618(13) 0.0398(11) 0.0499(12) 0.0039(9) 0.0341(11) 0.0023(9) C10 0.0477(11) 0.0310(10) 0.0406(11) -0.0003(8) 0.0253(9) 0.0045(8) O11 0.0608(10) 0.0700(11) 0.0387(8) -0.0191(8) 0.0264(7) -0.0155(7) O12 0.0473(8) 0.0787(11) 0.0433(9) 0.0153(7) 0.0240(7) 0.0016(8) 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 . 1.353(3) y C1 O11 . 1.368(2) y C1 C10 . 1.406(3) y C2 C3 . 1.396(3) y C2 H2 . 0.9300 ? C3 C4 . 1.342(3) y C3 O12 . 1.369(2) y C4 C5 . 1.404(3) y C4 H4 . 0.9300 ? C5 C6 . 1.406(3) y C5 C10 . 1.408(3) y C6 C7 . 1.350(3) y C6 H6 . 0.9300 ? C7 C8 . 1.396(3) y C7 H7 . 0.9300 ? C8 C9 . 1.352(3) y C8 H8 . 0.9300 ? C9 C10 . 1.403(3) y C9 H9 . 0.9300 ? O11 H11 . 0.85(3) ? O12 H12 . 0.89(3) ? 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 0.0000 '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 0.0000 '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 C1 O11 122.56(17) y C2 C1 C10 121.14(18) y O11 C1 C10 116.30(17) y C1 C2 C3 119.67(18) y C1 C2 H2 120.2 ? C3 C2 H2 120.2 ? C4 C3 O12 122.46(18) y C4 C3 C2 121.69(18) y O12 C3 C2 115.86(17) y C3 C4 C5 119.48(18) y C3 C4 H4 120.3 ? C5 C4 H4 120.3 ? C4 C5 C6 121.60(18) y C4 C5 C10 120.13(17) y C6 C5 C10 118.28(18) y C7 C6 C5 120.6(2) y C7 C6 H6 119.7 ? C5 C6 H6 119.7 ? C6 C7 C8 121.0(2) y C6 C7 H7 119.5 ? C8 C7 H7 119.5 ? C9 C8 C7 120.10(19) y C9 C8 H8 119.9 ? C7 C8 H8 119.9 ? C8 C9 C10 120.4(2) y C8 C9 H9 119.8 ? C10 C9 H9 119.8 ? C9 C10 C1 122.48(18) y C9 C10 C5 119.63(18) ? C1 C10 C5 117.89(17) y C1 O11 H11 110(2) ? C3 O12 H12 110.8(17) ? 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 O11 H11 O12 2_655 0.84(4) 1.89(4) 2.709(2) 163(3) y O12 H12 O11 4_575 0.90(2) 1.93(3) 2.766(2) 156(3) y C9 H9 Cg2 2_555 0.93 2.90 3.710(2) 146 y 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 O11 C1 C2 C3 179.44(17) C10 C1 C2 C3 0.1(3) C1 C2 C3 C4 -0.6(3) C1 C2 C3 O12 178.95(17) O12 C3 C4 C5 -179.12(17) C2 C3 C4 C5 0.4(3) C3 C4 C5 C6 179.95(18) C3 C4 C5 C10 0.2(3) C4 C5 C6 C7 -179.89(19) C10 C5 C6 C7 -0.2(3) C5 C6 C7 C8 0.9(3) C6 C7 C8 C9 -0.8(3) C7 C8 C9 C10 -0.1(3) C8 C9 C10 C1 -179.44(19) C8 C9 C10 C5 0.8(3) C2 C1 C10 C9 -179.22(18) O11 C1 C10 C9 1.4(3) C2 C1 C10 C5 0.5(3) O11 C1 C10 C5 -178.84(16) C4 C5 C10 C9 179.04(17) C6 C5 C10 C9 -0.7(3) C4 C5 C10 C1 -0.7(3) C6 C5 C10 C1 179.58(17) _cod_database_fobs_code 2014340