#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202526.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_2202526 loop_ _publ_author_name 'Kocaokutgen, Hasan' 'Soylu, M. Serkan' 'L\"ornecke, Peter' '\"Ozk\?inal\?i, Sevil' _publ_section_title ; 2-tert-Butyl-4-methyl-6-(phenyldiazenyl)phenol ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1932 _journal_page_last o1934 _journal_paper_doi 10.1107/S1600536803025261 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C17 H20 N2 O' _chemical_formula_moiety 'C17 H20 N2 O' _chemical_formula_sum 'C17 H20 N2 O' _chemical_formula_weight 268.35 _chemical_name_common 2-Hydroxy-3-tert-butyl-5-methylazobenzene _chemical_name_systematic ; 2-tert-butyl-4-metyl-6-(phenyldiazenyl)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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.2333(7) _cell_length_b 10.4182(12) _cell_length_c 22.788(3) _cell_measurement_reflns_used 12915 _cell_measurement_temperature 208(2) _cell_measurement_theta_max 31.84 _cell_measurement_theta_min 2.15 _cell_volume 1479.8(3) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 208(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _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 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 8784 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.15 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_correction_T_min 0.9850 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1998)' _exptl_crystal_colour Orange _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.151 _refine_diff_density_min -0.180 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 1543 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0369 _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^)+(0.0448P)^2^+0.273P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0853 _refine_ls_wR_factor_ref 0.0894 _reflns_number_gt 1355 _reflns_number_total 1543 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6296.cif _cod_data_source_block I _cod_database_code 2202526 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.1895(3) 0.02999(15) 0.20142(7) 0.0379(4) Uani d . 1 . . O H1 0.2884 0.0473 0.1791 0.057 Uiso calc R 1 . . H N1 0.4083(3) 0.01523(19) 0.10704(8) 0.0313(5) Uani d . 1 . . N N2 0.2864(3) -0.06981(18) 0.08529(8) 0.0306(4) Uani d . 1 . . N C1 0.5837(4) 0.0535(2) 0.07062(10) 0.0302(5) Uani d . 1 . . C C2 0.6092(4) 0.0120(2) 0.01294(10) 0.0373(6) Uani d . 1 . . C H2 0.5088 -0.0426 -0.0041 0.045 Uiso calc R 1 . . H C3 0.7857(4) 0.0528(2) -0.01870(11) 0.0427(6) Uani d . 1 . . C H3 0.8047 0.0252 -0.0572 0.051 Uiso calc R 1 . . H C4 0.9341(4) 0.1344(3) 0.00651(12) 0.0427(7) Uani d . 1 . . C H4 1.0523 0.1614 -0.0151 0.051 Uiso calc R 1 . . H C5 0.9083(4) 0.1761(3) 0.06334(11) 0.0420(6) Uani d . 1 . . C H5 1.0086 0.2310 0.0802 0.050 Uiso calc R 1 . . H C6 0.7321(4) 0.1357(2) 0.09535(11) 0.0352(6) Uani d . 1 . . C H6 0.7136 0.1641 0.1337 0.042 Uiso calc R 1 . . H C7 0.1107(4) -0.1087(2) 0.12009(10) 0.0285(5) Uani d . 1 . . C C8 0.0638(3) -0.0609(2) 0.17689(10) 0.0274(5) Uani d . 1 . . C C9 -0.1172(4) -0.1071(2) 0.20728(9) 0.0264(5) Uani d . 1 . . C C10 -0.2438(4) -0.1969(2) 0.17856(10) 0.0301(5) Uani d . 1 . . C H10 -0.3638 -0.2280 0.1982 0.036 Uiso calc R 1 . . H C11 -0.2030(4) -0.2438(2) 0.12196(10) 0.0320(5) Uani d . 1 . . C C12 -0.0225(4) -0.1987(2) 0.09399(10) 0.0314(5) Uani d . 1 . . C H12 0.0109 -0.2293 0.0568 0.038 Uiso calc R 1 . . H C13 -0.3528(4) -0.3379(2) 0.09345(11) 0.0404(6) Uani d . 1 . . C H13A -0.3003 -0.3593 0.0551 0.061 Uiso calc R 1 . . H H13B -0.4929 -0.3003 0.0901 0.061 Uiso calc R 1 . . H H13C -0.3611 -0.4143 0.1169 0.061 Uiso calc R 1 . . H C14 -0.1723(4) -0.0581(2) 0.26954(10) 0.0287(5) Uani d . 1 . . C C15 -0.2292(4) 0.0855(2) 0.26698(11) 0.0397(6) Uani d . 1 . . C H15A -0.2635 0.1155 0.3057 0.060 Uiso calc R 1 . . H H15B -0.3507 0.0977 0.2417 0.060 Uiso calc R 1 . . H H15C -0.1091 0.1328 0.2520 0.060 Uiso calc R 1 . . H C16 0.0164(4) -0.0798(3) 0.31134(10) 0.0419(6) Uani d . 1 . . C H16A -0.0206 -0.0489 0.3497 0.063 Uiso calc R 1 . . H H16B 0.1398 -0.0342 0.2972 0.063 Uiso calc R 1 . . H H16C 0.0483 -0.1698 0.3134 0.063 Uiso calc R 1 . . H C17 -0.3670(4) -0.1291(2) 0.29479(11) 0.0413(6) Uani d . 1 . . C H17A -0.3977 -0.0969 0.3334 0.062 Uiso calc R 1 . . H H17B -0.3361 -0.2192 0.2970 0.062 Uiso calc R 1 . . H H17C -0.4889 -0.1156 0.2698 0.062 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 0.0353(9) 0.0437(9) 0.0348(9) -0.0140(8) 0.0085(8) -0.0079(7) N1 0.0273(10) 0.0362(11) 0.0305(10) -0.0011(9) 0.0039(9) 0.0016(8) N2 0.0274(9) 0.0319(10) 0.0325(10) -0.0024(9) 0.0024(8) 0.0012(8) C1 0.0281(11) 0.0325(12) 0.0301(12) 0.0030(11) 0.0041(10) 0.0046(9) C2 0.0363(13) 0.0405(13) 0.0352(13) -0.0007(12) 0.0026(11) 0.0007(11) C3 0.0452(15) 0.0511(15) 0.0317(13) 0.0066(15) 0.0116(12) 0.0046(11) C4 0.0313(13) 0.0499(15) 0.0468(16) 0.0033(12) 0.0117(12) 0.0187(13) C5 0.0349(14) 0.0446(15) 0.0465(16) -0.0073(13) 0.0013(12) 0.0104(12) C6 0.0357(13) 0.0408(13) 0.0292(12) 0.0000(12) 0.0022(11) 0.0045(10) C7 0.0264(11) 0.0292(12) 0.0298(12) 0.0020(11) 0.0033(10) 0.0033(9) C8 0.0255(11) 0.0274(11) 0.0292(11) 0.0009(10) -0.0002(9) -0.0008(9) C9 0.0251(11) 0.0265(11) 0.0276(11) 0.0031(10) 0.0000(10) 0.0038(9) C10 0.0258(11) 0.0329(11) 0.0315(12) -0.0010(11) 0.0029(10) 0.0032(10) C11 0.0333(12) 0.0308(12) 0.0318(13) -0.0017(12) -0.0034(11) 0.0002(9) C12 0.0330(12) 0.0338(12) 0.0273(12) 0.0013(11) 0.0010(10) -0.0039(10) C13 0.0362(14) 0.0434(14) 0.0416(14) -0.0083(12) -0.0002(12) -0.0055(12) C14 0.0289(11) 0.0308(11) 0.0264(11) 0.0009(10) 0.0042(10) -0.0009(9) C15 0.0436(14) 0.0379(13) 0.0376(14) 0.0027(12) 0.0063(12) -0.0038(11) C16 0.0393(14) 0.0584(16) 0.0281(12) 0.0071(13) 0.0001(11) -0.0016(12) C17 0.0390(14) 0.0472(15) 0.0377(14) -0.0030(12) 0.0137(12) -0.0034(11) 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' N N 0.0061 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 C8 O1 H1 109.5 ? N2 N1 C1 115.24(19) yes N1 N2 C7 116.48(19) yes C6 C1 C2 120.1(2) ? C6 C1 N1 116.6(2) yes C2 C1 N1 123.3(2) yes C3 C2 C1 119.2(2) ? C3 C2 H2 120.4 ? C1 C2 H2 120.4 ? C4 C3 C2 120.4(2) ? C4 C3 H3 119.8 ? C2 C3 H3 119.8 ? C5 C4 C3 120.5(2) ? C5 C4 H4 119.7 ? C3 C4 H4 119.7 ? C4 C5 C6 119.6(3) ? C4 C5 H5 120.2 ? C6 C5 H5 120.2 ? C1 C6 C5 120.3(2) ? C1 C6 H6 119.8 ? C5 C6 H6 119.8 ? C12 C7 N2 114.7(2) yes C12 C7 C8 120.4(2) ? N2 C7 C8 124.9(2) ? O1 C8 C9 120.07(19) yes O1 C8 C7 120.32(19) yes C9 C8 C7 119.6(2) ? C10 C9 C8 117.0(2) yes C10 C9 C14 121.9(2) yes C8 C9 C14 121.1(2) ? C9 C10 C11 124.5(2) yes C9 C10 H10 117.8 ? C11 C10 H10 117.8 ? C12 C11 C10 117.1(2) yes C12 C11 C13 122.1(2) yes C10 C11 C13 120.8(2) ? C11 C12 C7 121.5(2) ? C11 C12 H12 119.3 ? C7 C12 H12 119.3 ? C11 C13 H13A 109.5 ? C11 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? C11 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? C16 C14 C17 107.66(19) ? C16 C14 C15 110.1(2) yes C17 C14 C15 107.5(2) ? C16 C14 C9 110.58(18) yes C17 C14 C9 111.16(19) yes C15 C14 C9 109.72(18) ? C14 C15 H15A 109.5 ? C14 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? C14 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? C14 C16 H16A 109.5 ? C14 C16 H16B 109.5 ? H16A C16 H16B 109.5 ? C14 C16 H16C 109.5 ? H16A C16 H16C 109.5 ? H16B C16 H16C 109.5 ? C14 C17 H17A 109.5 ? C14 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? C14 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? 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 O1 C8 . 1.350(3) yes O1 H1 . 0.82 ? N1 N2 . 1.268(2) yes N1 C1 . 1.429(3) yes N2 C7 . 1.411(3) yes C1 C6 . 1.381(3) ? C1 C2 . 1.393(3) ? C2 C3 . 1.383(3) ? C2 H2 . 0.93 ? C3 C4 . 1.381(4) ? C3 H3 . 0.93 ? C4 C5 . 1.375(4) ? C4 H4 . 0.93 ? C5 C6 . 1.384(3) ? C5 H5 . 0.93 ? C6 H6 . 0.93 ? C7 C12 . 1.387(3) ? C7 C8 . 1.417(3) ? C8 C9 . 1.409(3) ? C9 C10 . 1.388(3) ? C9 C14 . 1.546(3) ? C10 C11 . 1.403(3) ? C10 H10 . 0.93 ? C11 C12 . 1.376(3) ? C11 C13 . 1.502(3) ? C12 H12 . 0.93 ? C13 H13A . 0.96 ? C13 H13B . 0.96 ? C13 H13C . 0.96 ? C14 C16 . 1.530(3) ? C14 C17 . 1.533(3) ? C14 C15 . 1.538(3) ? C15 H15A . 0.96 ? C15 H15B . 0.96 ? C15 H15C . 0.96 ? C16 H16A . 0.96 ? C16 H16B . 0.96 ? C16 H16C . 0.96 ? C17 H17A . 0.96 ? C17 H17B . 0.96 ? C17 H17C . 0.96 ? 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 N1 . 0.82 1.83 2.551(2) 145 C16 H16B O1 . 0.96 2.30 2.958(3) 125 C15 H15C O1 . 0.96 2.44 3.063(3) 123 C4 H4 Cg1 4_555 0.93 2.90 3.625(3) 136 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 C1 N1 N2 C7 -179.46(19) yes N2 N1 C1 C6 -173.4(2) yes N2 N1 C1 C2 6.6(3) yes C6 C1 C2 C3 0.8(4) ? N1 C1 C2 C3 -179.1(2) ? C1 C2 C3 C4 -0.4(4) ? C2 C3 C4 C5 0.0(4) ? C3 C4 C5 C6 0.0(4) ? C2 C1 C6 C5 -0.8(4) ? N1 C1 C6 C5 179.1(2) ? C4 C5 C6 C1 0.4(4) ? N1 N2 C7 C12 178.03(19) yes N1 N2 C7 C8 -0.7(3) yes C12 C7 C8 O1 -177.7(2) ? N2 C7 C8 O1 0.9(3) y C12 C7 C8 C9 1.1(3) ? N2 C7 C8 C9 179.8(2) ? O1 C8 C9 C10 177.62(19) ? C7 C8 C9 C10 -1.3(3) ? O1 C8 C9 C14 -1.7(3) ? C7 C8 C9 C14 179.46(19) ? C8 C9 C10 C11 0.1(3) ? C14 C9 C10 C11 179.3(2) ? C9 C10 C11 C12 1.3(3) ? C9 C10 C11 C13 -178.0(2) ? C10 C11 C12 C7 -1.4(3) ? C13 C11 C12 C7 177.9(2) ? N2 C7 C12 C11 -178.6(2) ? C8 C7 C12 C11 0.2(3) ? C10 C9 C14 C16 124.1(2) ? C8 C9 C14 C16 -56.7(3) ? C10 C9 C14 C17 4.6(3) ? C8 C9 C14 C17 -176.2(2) ? C10 C9 C14 C15 -114.2(2) ? C8 C9 C14 C15 65.0(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654709 2 PubChem 137175825