#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206976.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_2206976 loop_ _publ_author_name 'Herrera, Ana M.' 'Bern\`es, Sylvain' 'L\'opez, Delia' _publ_section_title ; 4-(Hexylamino)phenol ; _journal_coeditor_code HG6242 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3210 _journal_page_last o3211 _journal_paper_doi 10.1107/S1600536805027868 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C12 H19 N O' _chemical_formula_moiety 'C12 H19 N O' _chemical_formula_sum 'C12 H19 N O' _chemical_formula_weight 193.28 _chemical_melting_point 348 _chemical_name_common 4-Hexylaminophenol _chemical_name_systematic 4-(n-Hexylamino)phenol _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens 'See text' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXTL-Plus _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.7016(6) _cell_length_b 10.1325(14) _cell_length_c 26.273(3) _cell_measurement_reflns_used 55 _cell_measurement_temperature 296.0(10) _cell_measurement_theta_max 11.90 _cell_measurement_theta_min 4.84 _cell_volume 1251.6(3) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXTL-Plus _computing_structure_refinement SHELXTL-Plus _computing_structure_solution 'SHELXTL-Plus (Sheldrick, 1998)' _diffrn_ambient_temperature 296.0(10) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method 2\q/\w _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 5524 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.15 _diffrn_standards_decay_% 3 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type none _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.026 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 424 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.113 _refine_diff_density_min -0.170 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 1327 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0531 _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^)+(0.1)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1389 _refine_ls_wR_factor_ref 0.1703 _reflns_number_gt 833 _reflns_number_total 1327 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hg6242.cif _cod_data_source_block I _cod_database_code 2206976 _cod_database_fobs_code 2206976 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 O1 0.1149(7) 0.5685(3) 0.32994(10) 0.0833(8) Uani d . 1 O H1A -0.028(11) 0.542(4) 0.3307(16) 0.098(18) Uiso d . 1 H N1 0.3464(8) 0.8998(3) 0.16515(12) 0.0754(9) Uani d . 1 N H1B 0.495(10) 0.925(4) 0.1686(15) 0.093(15) Uiso d . 1 H C1 0.1688(6) 0.6457(3) 0.28791(13) 0.0659(9) Uani d . 1 C C2 0.0336(7) 0.6269(4) 0.24204(14) 0.0756(10) Uani d . 1 C H2A -0.1008 0.5602 0.2387 0.091 Uiso calc R 1 H C3 0.0971(7) 0.7073(3) 0.20079(13) 0.0768(10) Uani d . 1 C H3A 0.0050 0.6933 0.1699 0.092 Uiso calc R 1 H C4 0.2953(6) 0.8079(3) 0.20483(13) 0.0660(9) Uani d . 1 C C5 0.4315(7) 0.8240(4) 0.25173(13) 0.0744(9) Uani d . 1 C H5A 0.5675 0.8899 0.2555 0.089 Uiso calc R 1 H C6 0.3674(7) 0.7438(3) 0.29239(14) 0.0765(9) Uani d . 1 C H6A 0.4600 0.7564 0.3233 0.092 Uiso calc R 1 H C7 0.3220(9) 0.8555(4) 0.11289(14) 0.0878(11) Uani d . 1 C H7A 0.1276 0.8287 0.1061 0.105 Uiso calc R 1 H H7B 0.4444 0.7797 0.1075 0.105 Uiso calc R 1 H C8 0.4068(10) 0.9663(4) 0.07655(15) 0.0992(13) Uani d . 1 C H8A 0.2828 1.0413 0.0823 0.119 Uiso calc R 1 H H8B 0.5995 0.9938 0.0844 0.119 Uiso calc R 1 H C9 0.3925(13) 0.9294(5) 0.02187(16) 0.1203(16) Uani d . 1 C H9A 0.1998 0.9026 0.0137 0.144 Uiso calc R 1 H H9B 0.5166 0.8545 0.0158 0.144 Uiso calc R 1 H C10 0.4811(15) 1.0442(5) -0.01366(18) 0.1311(18) Uani d . 1 C H10A 0.3490 1.1168 -0.0091 0.157 Uiso calc R 1 H H10B 0.6683 1.0750 -0.0037 0.157 Uiso calc R 1 H C11 0.4880(19) 1.0084(6) -0.0677(2) 0.168(2) Uani d . 1 C H11A 0.2979 0.9838 -0.0785 0.202 Uiso calc R 1 H H11B 0.6101 0.9321 -0.0721 0.202 Uiso calc R 1 H C12 0.593(2) 1.1177(7) -0.1009(2) 0.196(3) Uani d . 1 C H12A 0.5281 1.1040 -0.1351 0.294 Uiso calc R 1 H H12B 0.7975 1.1189 -0.1004 0.294 Uiso calc R 1 H H12C 0.5221 1.2005 -0.0885 0.294 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 0.0817(19) 0.0811(17) 0.0870(17) -0.0060(15) -0.0013(15) 0.0114(14) N1 0.077(2) 0.0712(19) 0.078(2) -0.0101(17) 0.0024(16) 0.0022(16) C1 0.0611(16) 0.0558(18) 0.081(2) 0.0055(16) 0.0013(17) 0.0081(18) C2 0.0687(18) 0.063(2) 0.095(2) -0.0132(16) -0.0019(19) 0.002(2) C3 0.079(2) 0.074(2) 0.077(2) -0.0062(19) -0.0107(19) -0.005(2) C4 0.0651(16) 0.0561(17) 0.077(2) 0.0022(15) 0.0044(17) -0.0031(19) C5 0.0671(17) 0.070(2) 0.086(2) -0.0114(17) -0.005(2) -0.0006(18) C6 0.0724(19) 0.075(2) 0.082(2) -0.0036(19) -0.0073(19) -0.005(2) C7 0.102(2) 0.079(2) 0.082(2) -0.005(2) 0.011(2) -0.007(2) C8 0.115(3) 0.099(3) 0.083(3) -0.010(3) 0.006(2) 0.002(2) C9 0.151(4) 0.115(3) 0.095(3) -0.004(4) 0.016(3) -0.003(3) C10 0.163(5) 0.135(4) 0.095(3) -0.009(4) 0.003(3) 0.006(3) C11 0.226(6) 0.150(5) 0.127(5) -0.003(6) 0.019(4) 0.012(4) C12 0.259(9) 0.187(6) 0.143(5) -0.027(7) 0.026(6) 0.058(5) 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' N N 0.0061 0.0033 '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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 1 -1 1 1 1 1 -1 -1 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 C1 O1 H1A 114(3) yes C4 N1 C7 118.6(3) yes C4 N1 H1B 107(3) yes C7 N1 H1B 107(3) yes C6 C1 C2 119.4(3) no C6 C1 O1 118.0(3) no C2 C1 O1 122.6(3) no C1 C2 C3 120.2(3) no C1 C2 H2A 119.9 no C3 C2 H2A 119.9 no C4 C3 C2 121.1(3) no C4 C3 H3A 119.5 no C2 C3 H3A 119.5 no C3 C4 C5 117.5(3) no C3 C4 N1 122.8(3) no C5 C4 N1 119.6(3) no C6 C5 C4 121.0(3) no C6 C5 H5A 119.5 no C4 C5 H5A 119.5 no C1 C6 C5 120.8(3) no C1 C6 H6A 119.6 no C5 C6 H6A 119.6 no N1 C7 C8 110.1(3) no N1 C7 H7A 109.6 no C8 C7 H7A 109.6 no N1 C7 H7B 109.6 no C8 C7 H7B 109.6 no H7A C7 H7B 108.2 no C9 C8 C7 114.1(4) no C9 C8 H8A 108.7 no C7 C8 H8A 108.7 no C9 C8 H8B 108.7 no C7 C8 H8B 108.7 no H8A C8 H8B 107.6 no C8 C9 C10 112.4(4) no C8 C9 H9A 109.1 no C10 C9 H9A 109.1 no C8 C9 H9B 109.1 no C10 C9 H9B 109.1 no H9A C9 H9B 107.9 no C11 C10 C9 113.8(5) no C11 C10 H10A 108.8 no C9 C10 H10A 108.8 no C11 C10 H10B 108.8 no C9 C10 H10B 108.8 no H10A C10 H10B 107.7 no C10 C11 C12 112.9(6) no C10 C11 H11A 109.0 no C12 C11 H11A 109.0 no C10 C11 H11B 109.0 no C12 C11 H11B 109.0 no H11A C11 H11B 107.8 no C11 C12 H12A 109.5 no C11 C12 H12B 109.5 no H12A C12 H12B 109.5 no C11 C12 H12C 109.5 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.377(4) yes O1 H1A 0.72(5) yes N1 C4 1.419(4) yes N1 C7 1.449(5) yes N1 H1B 0.75(5) yes C1 C6 1.369(4) no C1 C2 1.376(5) no C2 C3 1.388(5) no C2 H2A 0.9300 no C3 C4 1.385(4) no C3 H3A 0.9300 no C4 C5 1.398(4) no C5 C6 1.376(4) no C5 H5A 0.9300 no C6 H6A 0.9300 no C7 C8 1.527(5) yes C7 H7A 0.9700 no C7 H7B 0.9700 no C8 C9 1.486(6) yes C8 H8A 0.9700 no C8 H8B 0.9700 no C9 C10 1.549(7) yes C9 H9A 0.9700 no C9 H9B 0.9700 no C10 C11 1.466(8) yes C10 H10A 0.9700 no C10 H10B 0.9700 no C11 C12 1.494(8) yes C11 H11A 0.9700 no C11 H11B 0.9700 no C12 H12A 0.9600 no C12 H12B 0.9600 no C12 H12C 0.9600 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 O1 H1A N1 3_545 0.72(5) 2.08(5) 2.764(5) 158(5) yes N1 H1B O1 3_655 0.75(5) 2.34(5) 3.058(5) 161(4) 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 C3 -0.3(5) no O1 C1 C2 C3 -179.7(3) no C1 C2 C3 C4 -0.3(5) no C2 C3 C4 C5 0.9(5) no C2 C3 C4 N1 -173.8(3) no C7 N1 C4 C3 -33.8(5) no C7 N1 C4 C5 151.5(3) no C3 C4 C5 C6 -0.9(5) no N1 C4 C5 C6 174.1(3) no C2 C1 C6 C5 0.4(5) no O1 C1 C6 C5 179.8(3) no C4 C5 C6 C1 0.2(5) no C4 N1 C7 C8 -175.8(3) no N1 C7 C8 C9 179.2(4) no C7 C8 C9 C10 -179.8(4) no C8 C9 C10 C11 176.1(7) no C9 C10 C11 C12 -176.0(6) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 8233994 2 PubChem 10058440