#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/14/2011418.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_2011418 loop_ _publ_author_name 'Gerkin, Roger E.' _publ_section_title ; Hydrogen bonds and C---H···O interactions in N-(2-hydroxy-1,1-dimethylethyl)benzamide at 150K ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1218 _journal_page_last 1219 _journal_paper_doi 10.1107/S0108270100007629 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C11 H15 N1 O2' _chemical_formula_sum 'C11 H15 N O2' _chemical_formula_weight 193.24 _chemical_name_common ; N-(2-hydroxy-1,1-dimethylethyl)benzamide ; _chemical_name_systematic ; N-(2-hydroxy-1,1-dimethylethyl)benzamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 112.2995(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.4286(2) _cell_length_b 9.1195(2) _cell_length_c 11.3748(2) _cell_measurement_reflns_used 22319 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.93 _cell_volume 1000.88(3) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'TEXSAN and PLATON (Spek, 1990)' _computing_structure_refinement 'TEXSAN (Molecular Structure Corporation, 1992-1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .032 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 22319 _diffrn_reflns_theta_max 27.48 _exptl_absorpt_coefficient_mu .088 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_meas ? _exptl_crystal_description 'cut column' _exptl_crystal_F_000 416 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .27 _exptl_crystal_size_min .27 _refine_diff_density_max .23 _refine_diff_density_min -.22 _refine_ls_goodness_of_fit_ref 1.97 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 2293 _refine_ls_R_factor_gt .038 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^~cs~ + (0.032I)^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_ref .098 _reflns_number_gt 1936 _reflns_number_total 2293 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1281.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' 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_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C11 H15 N1 O2' _cod_database_code 2011418 _cod_database_fobs_code 2011418 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' 1/2-x,1/2+y,1/2-z ' -x, -y, -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_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy O1 .38115(7) .94206(8) .59498(6) .0300(2) Uani d ? . 1.000 O2 .19580(8) .73133(9) .54108(7) .0339(2) Uani d ? . 1.000 N1 .47517(9) .80918(9) .77665(8) .0222(2) Uani d ? . 1.000 C1 .55789(10) 1.05709(11) .76738(9) .0209(3) Uani d ? . 1.000 C2 .61404(10) 1.08217(11) .89781(9) .0251(3) Uani d ? . 1.000 C3 .69892(11) 1.20288(12) .94623(9) .0282(3) Uani d ? . 1.000 C4 .72969(11) 1.29820(11) .86598(10) .0282(3) Uani d ? . 1.000 C5 .67476(11) 1.27313(12) .73615(10) .0274(3) Uani d ? . 1.000 C6 .58854(10) 1.15414(11) .68683(9) .0246(3) Uani d ? . 1.000 C7 .46428(10) .93037(11) .70703(9) .0217(3) Uani d ? . 1.000 C8 .40992(10) .66479(11) .72703(9) .0216(3) Uani d ? . 1.000 C9 .25125(11) .67532(12) .66639(10) .0267(3) Uani d ? . 1.000 C10 .46951(12) .60438(13) .63300(10) .0280(3) Uani d ? . 1.000 C11 .44665(12) .56344(13) .84169(10) .0288(3) Uani d ? . 1.000 H1N1 .5361(13) .8083(14) .8512(12) .039(4) Uiso d ? . 1.000 H1O2 .2495(16) .8077(18) .5421(14) .070(5) Uiso d ? . 1.000 H2 .5937 1.0146 .9555 .030 Uiso c C2 . 1.000 H3 .7374 1.2207 1.0381 .034 Uiso c C3 . 1.000 H4 .7900 1.3829 .9008 .034 Uiso c C4 . 1.000 H5 .6970 1.3398 .6790 .033 Uiso c C5 . 1.000 H6 .5488 1.1380 .5948 .030 Uiso c C6 . 1.000 H9A .2203(11) .7366(13) .7255(10) .029(3) Uiso d ? . 1.000 H9B .2152(11) .5747(13) .6633(10) .026(3) Uiso d ? . 1.000 H10A .4260(12) .5107(15) .6003(10) .037(3) Uiso d ? . 1.000 H10B .4531(12) .6744(13) .5606(10) .033(3) Uiso d ? . 1.000 H10C .5732(13) .5886(12) .6787(10) .033(3) Uiso d ? . 1.000 H11A .4125(12) .4573(15) .8106(10) .038(3) Uiso d ? . 1.000 H11B .5461(14) .5600(14) .8882(11) .043(3) Uiso d ? . 1.000 H11C .4041(13) .5977(14) .9010(11) .043(3) Uiso d ? . 1.000 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 .0337(4) .0274(4) .0192(4) -.0051(3) -.0009(3) .0043(3) O2 .0291(5) .0295(5) .0275(4) -.0047(4) -.0068(3) .0054(3) N1 .0233(5) .0206(5) .0165(4) -.0012(4) .0008(4) .0020(3) C1 .0191(5) .0195(5) .0220(5) .0033(4) .0055(4) .0005(4) C2 .0275(6) .0245(6) .0225(5) .0026(4) .0085(4) .0010(4) C3 .0287(6) .0282(6) .0235(5) .0030(5) .0052(5) -.0063(4) C4 .0240(6) .0204(6) .0362(6) .0004(4) .0069(5) -.0051(5) C5 .0275(6) .0231(5) .0308(6) -.0001(4) .0102(5) .0022(4) C6 .0264(6) .0230(6) .0221(5) .0026(4) .0066(4) .0018(4) C7 .0231(5) .0225(5) .0181(5) .0012(4) .0064(4) .0014(4) C8 .0230(5) .0188(5) .0193(5) -.0013(4) .0036(4) .0013(4) C9 .0244(6) .0274(6) .0240(5) -.0011(5) .0043(5) .0006(5) C10 .0316(6) .0235(6) .0287(6) -.0019(5) .0110(5) -.0023(5) C11 .0322(7) .0237(6) .0248(5) -.0013(5) .0043(5) .0047(5) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 ; Stewart, R. F., Davidson, E. R. & Simpson, W. T. (1965). J. Chem. Phys. 42, 3174-3187. ; C .003 .002 ; Creagh, D. C. & McAuley, W. J. (1992). International Tables for X-ray Crystallography, Vol. C, pp. 219-222. Kluwer Academic Publishers, Dordrecht. ; N .006 .003 ; Creagh, D. C. & McAuley, W. J. (1992). International Tables for X-ray Crystallography, Vol. C, pp. 219-222. Kluwer Academic Publishers, Dordrecht. ; O .011 .006 ; Creagh, D. C. & McAuley, W. J. (1992). International Tables for X-ray Crystallography, Vol. C, pp. 219-222. Kluwer Academic Publishers, Dordrecht. ; 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 C9 O2 H1O2 104.7(9) no C7 N1 C8 125.51(8) yes C7 N1 H1N1 117.6(9) no C8 N1 H1N1 115.7(9) no C2 C1 C6 119.16(9) no C2 C1 C7 123.49(9) yes C6 C1 C7 117.36(8) yes C1 C2 C3 120.00(9) no C1 C2 H2 120.0 no C3 C2 H2 120.0 no C2 C3 C4 120.59(9) no C2 C3 H3 119.7 no C4 C3 H3 119.7 no C3 C4 C5 119.61(10) no C3 C4 H4 120.2 no C5 C4 H4 120.2 no C4 C5 C6 120.23(9) no C4 C5 H5 119.9 no C6 C5 H5 119.9 no C1 C6 C5 120.41(9) no C1 C6 H6 119.8 no C5 C6 H6 119.8 no O1 C7 N1 123.10(9) yes O1 C7 C1 118.81(9) yes N1 C7 C1 118.08(8) yes N1 C8 C9 111.97(8) no N1 C8 C10 109.55(8) no N1 C8 C11 106.33(8) no C9 C8 C10 111.29(8) no C9 C8 C11 107.49(8) no C10 C8 C11 110.07(9) no O2 C9 C8 115.73(8) yes O2 C9 H9B 107.2(6) no O2 C9 H9A 110.9(6) no C8 C9 H9B 106.8(6) no C8 C9 H9A 107.2(6) no H9B C9 H9A 108.8(9) no C8 C10 H10B 110.9(6) no C8 C10 H10C 109.2(6) no C8 C10 H10A 109.2(6) no H10B C10 H10C 109.1(9) no H10B C10 H10A 109.6(9) no H10C C10 H10A 108.8(9) no C8 C11 H11B 110.8(7) no C8 C11 H11C 111.1(7) no C8 C11 H11A 109.2(6) no H11B C11 H11C 107.6(9) no H11B C11 H11A 108.1(10) no H11C C11 H11A 109.9(10) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C7 . . 1.2446(11) yes O2 C9 . . 1.4148(13) yes O2 H1O2 . . .890(16) no N1 C7 . . 1.3391(12) yes N1 C8 . . 1.4913(12) yes N1 H1N1 . . .845(13) no C1 C2 . . 1.3918(13) no C1 C6 . . 1.3954(14) no C1 C7 . . 1.5004(14) yes C2 C3 . . 1.3888(15) no C2 H2 . . .98 no C3 C4 . . 1.3835(15) no C3 H3 . . .98 no C4 C5 . . 1.3853(15) no C4 H4 . . .98 no C5 C6 . . 1.3849(15) no C5 H5 . . .98 no C6 H6 . . .98 no C8 C9 . . 1.5352(14) no C8 C10 . . 1.5292(14) no C8 C11 . . 1.5241(14) no C9 H9B . . .987(11) no C9 H9A . . 1.017(11) no C10 H10A . . .973(13) no C10 H10B . . 1.004(11) no C10 H10C . . 1.016(12) no C11 H11A . . 1.045(13) no C11 H11B . . .969(13) no C11 H11C . . .988(13) 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 O2 H1O2 O1 ? .89(2) 1.77(2) 2.6279(11) 161.8(14) yes N1 H1N1 O2 4_565 .85(2) 2.20(2) 3.0374(11) 171.0(12) yes C2 H2 O2 4_565 .98 2.52 3.2407(13) 131 yes C4 H4 O1 4_575 .98 2.60 3.4305(12) 143 yes C6 H6 O1 3_676 .98 2.63 3.4517(12) 141 yes C11 H11B O2 4_565 .97(2) 2.65(2) 3.3054(14) 125.2(9) 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 O1 C7 N1 C8 10.89(16) no O1 C7 C1 C2 154.49(10) no O1 C7 C1 C6 -25.19(13) no O2 C9 C8 N1 79.90(11) no O2 C9 C8 C10 -43.09(13) no O2 C9 C8 C11 -163.68(9) no N1 C7 C1 C2 -25.98(14) no N1 C7 C1 C6 154.33(9) no C1 C2 C3 C4 -.70(15) no C1 C6 C5 C4 -1.03(15) no C1 C7 N1 C8 -168.61(9) no C2 C1 C6 C5 .60(14) no C2 C3 C4 C5 .27(15) no C3 C2 C1 C6 .26(15) no C3 C2 C1 C7 -179.42(9) no C3 C4 C5 C6 .59(15) no C5 C6 C1 C7 -179.70(9) no C7 N1 C8 C9 -60.68(12) no C7 N1 C8 C10 63.28(12) no C7 N1 C8 C11 -177.80(9) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 555352 2 PubChem 639965