#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/35/2203597.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_2203597 loop_ _publ_author_name 'Rozycka-Sokolowska, Ewa' 'Marciniak, Bernard' 'Pavlyuk, Volodymyr' _publ_section_title ; Redetermination of 1-naphthalenol ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o884 _journal_page_last o885 _journal_paper_doi 10.1107/S1600536804009225 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C10 H8 O' _chemical_formula_moiety 'C10 H8 O' _chemical_formula_sum 'C10 H8 O' _chemical_formula_weight 144.16 _chemical_name_common 1-naphthol _chemical_name_systematic ; 1-naphthalenol ; _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 117.12(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.171(2) _cell_length_b 4.7980(10) _cell_length_c 13.276(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20 _cell_measurement_theta_min 5 _cell_volume 746.7(3) _computing_cell_refinement 'KM4B8 software' _computing_data_collection 'KM4B8 software (Galdecki et al., 1996)' _computing_data_reduction 'KM4B8 software' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2000)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'Please provide missing details' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'Kuma KM-4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 3416 _diffrn_reflns_theta_full 27.45 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 1.74 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(DIFABS; Walker & Stuart, 1983)' _exptl_crystal_colour 'pale white' _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description columnar _exptl_crystal_F_000 304 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.085 _refine_diff_density_min -0.159 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 103 _refine_ls_number_reflns 1708 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0374 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0217P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1055 _refine_ls_wR_factor_ref 0.1125 _reflns_number_gt 1197 _reflns_number_total 1708 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fl6101.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 2203597 _cod_database_fobs_code 2203597 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_type_symbol C10 0.30026(10) 0.0138(2) 0.27720(10) 0.0470(3) Uani d . 1 C O1 0.46036(8) 0.2257(2) 0.27353(10) 0.0651(3) Uani d . 1 O H1 0.4784 0.3686 0.2518 0.098 Uiso calc R 1 H C5 0.18092(11) -0.0162(3) 0.22942(11) 0.0507(3) Uani d . 1 C C1 0.34334(10) 0.2052(3) 0.22419(12) 0.0488(3) Uani d . 1 C C2 0.27407(12) 0.3535(3) 0.13118(13) 0.0573(3) Uani d . 1 C H2 0.3049 0.4766 0.0983 0.069 Uiso calc R 1 H C4 0.11065(11) 0.1426(3) 0.13223(12) 0.0599(4) Uani d . 1 C H4 0.0318 0.1239 0.1006 0.072 Uiso calc R 1 H C3 0.15582(12) 0.3199(3) 0.08499(12) 0.0622(4) Uani d . 1 C H3 0.1080 0.4209 0.0210 0.075 Uiso calc R 1 H C8 0.32453(16) -0.3238(3) 0.42239(14) 0.0709(4) Uani d . 1 C H8 0.3716 -0.4264 0.4862 0.085 Uiso calc R 1 H C9 0.37066(12) -0.1449(3) 0.37505(12) 0.0574(3) Uani d . 1 C H9 0.4495 -0.1258 0.4071 0.069 Uiso calc R 1 H C7 0.20626(16) -0.3528(4) 0.37490(16) 0.0755(5) Uani d . 1 C H7 0.1748 -0.4753 0.4073 0.091 Uiso calc R 1 H C6 0.13740(14) -0.2054(3) 0.28271(14) 0.0664(4) Uani d . 1 C H6 0.0589 -0.2278 0.2529 0.080 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 C10 0.0451(6) 0.0399(6) 0.0573(7) -0.0011(5) 0.0246(6) -0.0113(5) O1 0.0420(5) 0.0540(6) 0.0989(8) -0.0032(4) 0.0317(5) 0.0023(5) C5 0.0469(6) 0.0489(7) 0.0616(8) -0.0060(5) 0.0291(6) -0.0154(6) C1 0.0394(6) 0.0420(6) 0.0670(8) -0.0016(5) 0.0260(5) -0.0090(5) C2 0.0577(8) 0.0498(7) 0.0702(9) 0.0036(6) 0.0343(7) 0.0038(6) C4 0.0426(6) 0.0686(9) 0.0652(9) -0.0012(6) 0.0217(6) -0.0135(7) C3 0.0546(8) 0.0654(9) 0.0589(8) 0.0116(7) 0.0191(6) 0.0016(7) C8 0.0916(12) 0.0584(9) 0.0650(9) 0.0056(8) 0.0378(9) 0.0038(7) C9 0.0527(7) 0.0537(7) 0.0615(8) 0.0017(6) 0.0223(6) -0.0048(6) C7 0.0939(12) 0.0640(9) 0.0913(12) -0.0115(8) 0.0619(11) -0.0021(8) C6 0.0598(8) 0.0689(9) 0.0797(10) -0.0131(7) 0.0399(8) -0.0118(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 0.0000 '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 C5 C10 C1 117.25(12) C5 C10 C9 119.00(12) C1 C10 C9 123.75(12) C1 O1 H1 109.5 C10 C5 C4 119.06(13) C10 C5 C6 117.47(13) C4 C5 C6 123.47(13) C2 C1 O1 122.61(12) C2 C1 C10 122.34(12) O1 C1 C10 115.05(12) C1 C2 C3 119.43(13) C1 C2 H2 120.3 C3 C2 H2 120.3 C3 C4 C5 121.31(13) C3 C4 H4 119.3 C5 C4 H4 119.3 C4 C3 C2 120.60(14) C4 C3 H3 119.7 C2 C3 H3 119.7 C9 C8 C7 119.73(16) C9 C8 H8 120.1 C7 C8 H8 120.1 C8 C9 C10 121.12(14) C8 C9 H9 119.4 C10 C9 H9 119.4 C6 C7 C8 120.63(15) C6 C7 H7 119.7 C8 C7 H7 119.7 C7 C6 C5 122.06(14) C7 C6 H6 119.0 C5 C6 H6 119.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C10 C5 1.4088(16) C10 C1 1.4229(18) C10 C9 1.4245(19) O1 C1 1.3761(14) O1 H1 0.8200 C5 C4 1.419(2) C5 C6 1.4222(19) C1 C2 1.3550(19) C2 C3 1.399(2) C2 H2 0.9300 C4 C3 1.345(2) C4 H4 0.9300 C3 H3 0.9300 C8 C9 1.360(2) C8 C7 1.396(2) C8 H8 0.9300 C9 H9 0.9300 C7 C6 1.345(2) C7 H7 0.9300 C6 H6 0.9300 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 O1 H1 O1 2_655 0.82 1.99 2.7980(10) 170 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 C1 C10 C5 C4 0.14(17) C9 C10 C5 C4 179.73(11) C1 C10 C5 C6 -179.44(11) C9 C10 C5 C6 0.15(17) C5 C10 C1 C2 -0.34(18) C9 C10 C1 C2 -179.91(12) C5 C10 C1 O1 -179.59(10) C9 C10 C1 O1 0.84(18) O1 C1 C2 C3 179.39(12) C10 C1 C2 C3 0.2(2) C10 C5 C4 C3 0.2(2) C6 C5 C4 C3 179.76(13) C5 C4 C3 C2 -0.4(2) C1 C2 C3 C4 0.2(2) C7 C8 C9 C10 -0.2(2) C5 C10 C9 C8 0.11(19) C1 C10 C9 C8 179.67(12) C9 C8 C7 C6 0.0(2) C8 C7 C6 C5 0.3(2) C10 C5 C6 C7 -0.3(2) C4 C5 C6 C7 -179.91(14) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 6739 2 PubChem 7005