#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200454.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_2200454 loop_ _publ_author_name 'Abdul Ajees, A.' 'Sekar, K.' 'Marrappan, M.' 'Kandasamy, M.' _publ_section_title ; 4-tert-Butyl-2,6-bis(piperidinomethyl)phenol ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o878 _journal_page_last o880 _journal_paper_doi 10.1107/S1600536801013836 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C22 H36 N2 O' _chemical_formula_moiety 'C22 H36 N2 O' _chemical_formula_sum 'C22 H36 N2 O' _chemical_formula_weight 344.53 _chemical_name_systematic ; 4-tert-Butyl-2,6-bis(piperidinomethyl)phenol ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL-97 _cell_angle_alpha 106.20(3) _cell_angle_beta 116.89(3) _cell_angle_gamma 87.18(4) _cell_formula_units_Z 2 _cell_length_a 10.540(2) _cell_length_b 12.153(3) _cell_length_c 9.786(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30 _cell_measurement_theta_min 15 _cell_volume 1069.2(5) _computing_cell_refinement 'SDP (Frenz, 1978)' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CAD-4 Software' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .966 _diffrn_measured_fraction_theta_max .966 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .017 _diffrn_reflns_av_sigmaI/netI .0096 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4237 _diffrn_reflns_theta_full 69.91 _diffrn_reflns_theta_max 69.91 _diffrn_reflns_theta_min 4.72 _diffrn_standards_decay_% <1 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .496 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 380 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _refine_diff_density_max .27 _refine_diff_density_min -.18 _refine_ls_extinction_coef .022(4) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 234 _refine_ls_number_reflns 3904 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.09 _refine_ls_R_factor_all .059 _refine_ls_R_factor_gt .057 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0939P)^2^+0.2502P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .176 _reflns_number_gt 3680 _reflns_number_total 3904 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6052.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 1069.2(4) _cod_database_code 2200454 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 C1 .72334(16) -.00083(13) .45577(18) .0461(4) Uani d . 1 . . C C2 .82952(16) -.01431(13) .60038(18) .0465(4) Uani d . 1 . . C C3 .80763(16) -.10284(13) .65378(18) .0477(4) Uani d . 1 . . C H3 .8774 -.1111 .7507 .057 Uiso calc R 1 . . H C4 .68568(16) -.17951(13) .56811(18) .0461(4) Uani d . 1 . . C C5 .58284(16) -.16262(13) .42497(18) .0495(4) Uani d . 1 . . C H5 .4999 -.2125 .3654 .059 Uiso calc R 1 . . H C6 .59874(17) -.07498(13) .36760(18) .0483(4) Uani d . 1 . . C C7 .4822(2) -.05780(15) .2142(2) .0613(5) Uani d . 1 . . C H7A .4193 -.0045 .2400 .074 Uiso calc R 1 . . H H7B .5255 -.0229 .1657 .074 Uiso calc R 1 . . H N8 .39737(13) -.16342(11) .09812(15) .0485(3) Uani d . 1 . . N C9 .48005(19) -.23846(18) .0321(2) .0646(5) Uani d . 1 . . C H9A .5635 -.2557 .1185 .078 Uiso calc R 1 . . H H9B .5127 -.1989 -.0213 .078 Uiso calc R 1 . . H C10 .3937(3) -.34948(19) -.0855(3) .0799(6) Uani d . 1 . . C H10A .3670 -.3920 -.0307 .096 Uiso calc R 1 . . H H10B .4514 -.3963 -.1291 .096 Uiso calc R 1 . . H C11 .2602(2) -.32599(19) -.2207(2) .0737(6) Uani d . 1 . . C H11A .2863 -.2937 -.2856 .088 Uiso calc R 1 . . H H11B .2008 -.3974 -.2884 .088 Uiso calc R 1 . . H C12 .1787(2) -.24332(19) -.1528(2) .0703(5) Uani d . 1 . . C H12A .1397 -.2809 -.1028 .084 Uiso calc R 1 . . H H12B .0994 -.2220 -.2390 .084 Uiso calc R 1 . . H C13 .27125(19) -.13614(17) -.0310(2) .0618(5) Uani d . 1 . . C H13A .3015 -.0939 -.0835 .074 Uiso calc R 1 . . H H13B .2158 -.0872 .0140 .074 Uiso calc R 1 . . H C14 .97089(17) .05913(15) .6921(2) .0569(4) Uani d . 1 . . C H14A 1.0118 .0612 .8038 .068 Uiso calc R 1 . . H H14B 1.0361 .0236 .6513 .068 Uiso calc R 1 . . H N15 .95811(13) .17729(11) .68092(15) .0484(3) Uani d . 1 . . N C16 .89039(18) .24444(16) .7748(2) .0581(4) Uani d . 1 . . C H16A .9490 .2498 .8869 .070 Uiso calc R 1 . . H H16B .7981 .2059 .7404 .070 Uiso calc R 1 . . H C17 .8712(2) .36361(17) .7546(3) .0782(6) Uani d . 1 . . C H17A .8278 .4072 .8193 .094 Uiso calc R 1 . . H H17B .8077 .3585 .6436 .094 Uiso calc R 1 . . H C18 1.0137(2) .42514(18) .8046(3) .0864(7) Uani d . 1 . . C H18A .9991 .4995 .7839 .104 Uiso calc R 1 . . H H18B 1.0739 .4378 .9184 .104 Uiso calc R 1 . . H C19 1.0858(2) .35312(19) .7117(3) .0784(6) Uani d . 1 . . C H19A 1.0308 .3486 .5994 .094 Uiso calc R 1 . . H H19B 1.1801 .3896 .7497 .094 Uiso calc R 1 . . H C20 1.09879(18) .23394(16) .7303(2) .0608(5) Uani d . 1 . . C H20A 1.1412 .1886 .6657 .073 Uiso calc R 1 . . H H20B 1.1613 .2380 .8412 .073 Uiso calc R 1 . . H O21 .74069(14) .08386(10) .39626(14) .0593(4) Uani d . 1 . . O H21 .817(3) .134(2) .486(3) .086(7) Uiso d . 1 . . H C22 .66688(18) -.28185(15) .6221(2) .0544(4) Uani d . 1 . . C C23 .7545(4) -.2597(3) .8016(3) .1203(12) Uani d . 1 . . C H23A .7254 -.1928 .8560 .180 Uiso calc R 1 . . H H23B .8539 -.2474 .8309 .180 Uiso calc R 1 . . H H23C .7397 -.3250 .8314 .180 Uiso calc R 1 . . H C24 .5126(2) -.3062(3) .5805(4) .1067(10) Uani d . 1 . . C H24A .5060 -.3609 .6319 .160 Uiso calc R 1 . . H H24B .4578 -.3372 .4667 .160 Uiso calc R 1 . . H H24C .4760 -.2362 .6165 .160 Uiso calc R 1 . . H C25 .7177(4) -.3855(2) .5399(5) .1194(12) Uani d . 1 . . C H25A .7099 -.4500 .5750 .179 Uiso calc R 1 . . H H25B .8155 -.3691 .5662 .179 Uiso calc R 1 . . H H25C .6599 -.4034 .4262 .179 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 C1 .0499(8) .0419(8) .0464(8) .0039(6) .0207(7) .0149(6) C2 .0424(8) .0444(8) .0490(8) .0034(6) .0176(6) .0136(6) C3 .0435(8) .0507(8) .0443(8) .0062(6) .0135(6) .0188(6) C4 .0447(8) .0475(8) .0466(8) .0050(6) .0189(6) .0179(6) C5 .0437(8) .0481(8) .0487(8) -.0018(6) .0132(7) .0151(7) C6 .0480(8) .0464(8) .0438(8) .0034(6) .0148(7) .0140(6) C7 .0632(10) .0527(9) .0507(9) -.0001(8) .0079(8) .0204(7) N8 .0433(7) .0533(7) .0420(7) .0033(5) .0124(5) .0161(6) C9 .0490(9) .0801(12) .0575(10) .0105(8) .0196(8) .0181(9) C10 .0879(15) .0713(13) .0655(12) .0175(11) .0296(11) .0091(10) C11 .0752(13) .0779(13) .0511(10) -.0097(10) .0207(9) .0054(9) C12 .0489(9) .0932(14) .0537(10) -.0060(9) .0126(8) .0160(9) C13 .0512(9) .0722(11) .0501(9) .0107(8) .0112(7) .0220(8) C14 .0428(8) .0535(9) .0663(10) .0027(7) .0165(7) .0198(8) N15 .0436(7) .0474(7) .0517(7) -.0028(5) .0203(6) .0121(6) C16 .0483(9) .0649(10) .0572(9) -.0001(7) .0242(7) .0108(8) C17 .0599(11) .0563(11) .0958(15) .0037(8) .0271(10) .0033(10) C18 .0737(13) .0519(11) .1082(18) -.0070(9) .0269(12) .0092(11) C19 .0746(13) .0726(13) .0852(14) -.0203(10) .0314(11) .0233(11) C20 .0495(9) .0633(11) .0681(11) -.0077(7) .0290(8) .0107(8) O21 .0642(7) .0542(7) .0538(7) -.0056(6) .0164(6) .0239(5) C22 .0516(9) .0558(9) .0590(9) .0021(7) .0213(7) .0275(8) C23 .135(2) .132(2) .0777(16) -.043(2) .0102(16) .0637(16) C24 .0648(13) .130(2) .157(3) .0051(13) .0445(15) .098(2) C25 .188(3) .0670(14) .175(3) .0439(17) .130(3) .0631(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 '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 O21 C1 C6 118.56(14) O21 C1 C2 120.97(14) C6 C1 C2 120.47(14) C3 C2 C1 118.62(14) C3 C2 C14 119.70(14) C1 C2 C14 121.52(14) C2 C3 C4 122.59(14) C2 C3 H3 118.7 C4 C3 H3 118.7 C3 C4 C5 116.74(14) C3 C4 C22 122.24(14) C5 C4 C22 120.95(14) C6 C5 C4 122.89(14) C6 C5 H5 118.6 C4 C5 H5 118.6 C5 C6 C1 118.68(14) C5 C6 C7 120.99(15) C1 C6 C7 120.31(14) N8 C7 C6 113.98(14) N8 C7 H7A 108.8 C6 C7 H7A 108.8 N8 C7 H7B 108.8 C6 C7 H7B 108.8 H7A C7 H7B 107.7 C9 N8 C7 111.54(14) C9 N8 C13 109.86(14) C7 N8 C13 109.93(14) N8 C9 C10 111.82(16) N8 C9 H9A 109.3 C10 C9 H9A 109.3 N8 C9 H9B 109.3 C10 C9 H9B 109.3 H9A C9 H9B 107.9 C9 C10 C11 110.87(18) C9 C10 H10A 109.5 C11 C10 H10A 109.5 C9 C10 H10B 109.5 C11 C10 H10B 109.5 H10A C10 H10B 108.1 C12 C11 C10 109.59(16) C12 C11 H11A 109.8 C10 C11 H11A 109.8 C12 C11 H11B 109.8 C10 C11 H11B 109.8 H11A C11 H11B 108.2 C11 C12 C13 112.08(16) C11 C12 H12A 109.2 C13 C12 H12A 109.2 C11 C12 H12B 109.2 C13 C12 H12B 109.2 H12A C12 H12B 107.9 N8 C13 C12 111.72(16) N8 C13 H13A 109.3 C12 C13 H13A 109.3 N8 C13 H13B 109.3 C12 C13 H13B 109.3 H13A C13 H13B 107.9 N15 C14 C2 113.29(13) N15 C14 H14A 108.9 C2 C14 H14A 108.9 N15 C14 H14B 108.9 C2 C14 H14B 108.9 H14A C14 H14B 107.7 C16 N15 C14 111.63(14) C16 N15 C20 110.76(13) C14 N15 C20 110.78(14) N15 C16 C17 110.76(16) N15 C16 H16A 109.5 C17 C16 H16A 109.5 N15 C16 H16B 109.5 C17 C16 H16B 109.5 H16A C16 H16B 108.1 C16 C17 C18 110.61(17) C16 C17 H17A 109.5 C18 C17 H17A 109.5 C16 C17 H17B 109.5 C18 C17 H17B 109.5 H17A C17 H17B 108.1 C19 C18 C17 109.48(17) C19 C18 H18A 109.8 C17 C18 H18A 109.8 C19 C18 H18B 109.8 C17 C18 H18B 109.8 H18A C18 H18B 108.2 C20 C19 C18 111.11(18) C20 C19 H19A 109.4 C18 C19 H19A 109.4 C20 C19 H19B 109.4 C18 C19 H19B 109.4 H19A C19 H19B 108.0 N15 C20 C19 111.15(16) N15 C20 H20A 109.4 C19 C20 H20A 109.4 N15 C20 H20B 109.4 C19 C20 H20B 109.4 H20A C20 H20B 108.0 C1 O21 H21 103.3(14) C24 C22 C25 110.0(2) C24 C22 C23 107.6(2) C25 C22 C23 108.3(2) C24 C22 C4 111.08(15) C25 C22 C4 108.15(15) C23 C22 C4 111.65(16) C22 C23 H23A 109.5 C22 C23 H23B 109.5 H23A C23 H23B 109.5 C22 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 C22 C24 H24A 109.5 C22 C24 H24B 109.5 H24A C24 H24B 109.5 C22 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 C22 C25 H25A 109.5 C22 C25 H25B 109.5 H25A C25 H25B 109.5 C22 C25 H25C 109.5 H25A C25 H25C 109.5 H25B C25 H25C 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 C1 O21 . 1.3715(18) ? C1 C6 . 1.392(2) ? C1 C2 . 1.400(2) ? C2 C3 . 1.390(2) ? C2 C14 . 1.515(2) ? C3 C4 . 1.389(2) ? C3 H3 . .93 ? C4 C5 . 1.394(2) ? C4 C22 . 1.534(2) ? C5 C6 . 1.383(2) ? C5 H5 . .93 ? C6 C7 . 1.512(2) ? C7 N8 . 1.455(2) ? C7 H7A . .97 ? C7 H7B . .97 ? N8 C9 . 1.453(2) ? N8 C13 . 1.464(2) ? C9 C10 . 1.510(3) ? C9 H9A . .97 ? C9 H9B . .97 ? C10 C11 . 1.516(3) ? C10 H10A . .97 ? C10 H10B . .97 ? C11 C12 . 1.499(3) ? C11 H11A . .97 ? C11 H11B . .97 ? C12 C13 . 1.509(3) ? C12 H12A . .97 ? C12 H12B . .97 ? C13 H13A . .97 ? C13 H13B . .97 ? C14 N15 . 1.465(2) ? C14 H14A . .97 ? C14 H14B . .97 ? N15 C16 . 1.462(2) ? N15 C20 . 1.474(2) ? C16 C17 . 1.507(3) ? C16 H16A . .97 ? C16 H16B . .97 ? C17 C18 . 1.516(3) ? C17 H17A . .97 ? C17 H17B . .97 ? C18 C19 . 1.512(3) ? C18 H18A . .97 ? C18 H18B . .97 ? C19 C20 . 1.502(3) ? C19 H19A . .97 ? C19 H19B . .97 ? C20 H20A . .97 ? C20 H20B . .97 ? O21 H21 . .95(3) ? C22 C24 . 1.510(3) ? C22 C25 . 1.510(3) ? C22 C23 . 1.518(3) ? C23 H23A . .96 ? C23 H23B . .96 ? C23 H23C . .96 ? C24 H24A . .96 ? C24 H24B . .96 ? C24 H24C . .96 ? C25 H25A . .96 ? C25 H25B . .96 ? C25 H25C . .96 ? 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 O21 C1 C2 C3 -178.83(14) C6 C1 C2 C3 -.1(2) O21 C1 C2 C14 -3.6(2) C6 C1 C2 C14 175.14(15) C1 C2 C3 C4 1.1(2) C14 C2 C3 C4 -174.30(15) C2 C3 C4 C5 -1.1(2) C2 C3 C4 C22 175.76(14) C3 C4 C5 C6 .3(2) C22 C4 C5 C6 -176.62(15) C4 C5 C6 C1 .5(3) C4 C5 C6 C7 -178.09(16) O21 C1 C6 C5 178.09(14) C2 C1 C6 C5 -.6(2) O21 C1 C6 C7 -3.3(2) C2 C1 C6 C7 178.00(15) C5 C6 C7 N8 -30.3(2) C1 C6 C7 N8 151.13(16) C6 C7 N8 C9 -69.1(2) C6 C7 N8 C13 168.78(15) C7 N8 C9 C10 178.63(15) C13 N8 C9 C10 -59.2(2) N8 C9 C10 C11 57.6(2) C9 C10 C11 C12 -53.1(3) C10 C11 C12 C13 52.5(2) C9 N8 C13 C12 57.9(2) C7 N8 C13 C12 -179.00(16) C11 C12 C13 N8 -55.8(2) C3 C2 C14 N15 -149.72(15) C1 C2 C14 N15 35.1(2) C2 C14 N15 C16 72.54(18) C2 C14 N15 C20 -163.52(14) C14 N15 C16 C17 -176.98(14) C20 N15 C16 C17 59.07(19) N15 C16 C17 C18 -58.1(2) C16 C17 C18 C19 55.3(3) C17 C18 C19 C20 -54.7(3) C16 N15 C20 C19 -58.3(2) C14 N15 C20 C19 177.27(16) C18 C19 C20 N15 56.4(2) C3 C4 C22 C24 145.9(2) C5 C4 C22 C24 -37.4(3) C3 C4 C22 C25 -93.3(2) C5 C4 C22 C25 83.4(2) C3 C4 C22 C23 25.7(3) C5 C4 C22 C23 -157.5(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4425350 2 PubChem 5260204