#------------------------------------------------------------------------------ #$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/37/2013788.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_2013788 loop_ _publ_author_name 'Wu, Yao-Wen' 'Wang, Ru-Ji' 'Jiang, Yu-Yang' 'Fu, Hua' 'Zhao, Yu-Fen' _publ_section_title ; Displaced \p--\p stacking and hydrogen bonds in 3-bromo-N-(2-hydroxy-1,1-dimethylethyl)benzamide ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o178 _journal_page_last o179 _journal_paper_doi 10.1107/S0108270103025824 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C11 H14 Br N O2' _chemical_formula_moiety 'C11 H14 Br N O2' _chemical_formula_sum 'C11 H14 Br N O2' _chemical_formula_weight 272.14 _chemical_name_systematic ; 2-bromo-N-(2-hydroxy-1,1-dimethylethyl)benzamide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 77.123(11) _cell_angle_beta 77.785(12) _cell_angle_gamma 79.825(10) _cell_formula_units_Z 2 _cell_length_a 7.2713(10) _cell_length_b 8.5860(9) _cell_length_c 9.8424(14) _cell_measurement_reflns_used 34 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.8 _cell_measurement_theta_min 4.9 _cell_volume 580.03(13) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Bruker, 1997)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker P4' _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 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2551 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.16 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 3.524 _exptl_absorpt_correction_T_max 0.350 _exptl_absorpt_correction_T_min 0.242 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 276 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.615 _refine_diff_density_min -0.711 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 2034 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0370 _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^)+(0.001P)^2^+1.5P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0869 _refine_ls_wR_factor_ref 0.0966 _reflns_number_gt 1748 _reflns_number_total 2034 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gd1280.cif _cod_data_source_block I _cod_database_code 2013788 _cod_database_fobs_code 2013788 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 Br1 1.28291(7) 0.12781(7) 0.59471(6) 0.0686(2) Uani d . 1 . . Br O1 0.5476(4) 0.6258(4) 0.7915(3) 0.0561(8) Uani d . 1 . . O O2 0.7493(4) 0.5503(4) 1.1278(3) 0.0518(7) Uani d . 1 . . O H2B 0.6706 0.4874 1.1568 0.078 Uiso calc R 1 . . H N1 0.8426(4) 0.6318(4) 0.8265(3) 0.0429(8) Uani d . 1 . . N H1A 0.9604 0.5927 0.8076 0.051 Uiso calc R 1 . . H C1 0.7960(5) 0.4455(5) 0.6864(4) 0.0409(9) Uani d . 1 . . C C2 0.9795(5) 0.3619(5) 0.6807(4) 0.0438(9) Uani d . 1 . . C H2A 1.0616 0.3824 0.7334 0.053 Uiso calc R 1 . . H C3 1.0367(5) 0.2489(5) 0.5961(4) 0.0447(9) Uani d . 1 . . C C4 0.9226(6) 0.2183(5) 0.5123(4) 0.0481(10) Uani d . 1 . . C H4A 0.9662 0.1443 0.4527 0.058 Uiso calc R 1 . . H C5 0.7407(6) 0.3018(5) 0.5200(5) 0.0533(11) Uani d . 1 . . C H5A 0.6600 0.2827 0.4655 0.064 Uiso calc R 1 . . H C6 0.6781(6) 0.4115(5) 0.6060(5) 0.0499(10) Uani d . 1 . . C H6A 0.5544 0.4645 0.6110 0.060 Uiso calc R 1 . . H C7 0.7194(5) 0.5740(5) 0.7734(4) 0.0438(9) Uani d . 1 . . C C8 0.7938(6) 0.7563(5) 0.9142(4) 0.0466(9) Uani d . 1 . . C C9 0.6649(6) 0.6969(5) 1.0544(5) 0.0513(10) Uani d . 1 . . C H9A 0.6403 0.7778 1.1132 0.062 Uiso calc R 1 . . H H9B 0.5443 0.6817 1.0355 0.062 Uiso calc R 1 . . H C10 0.9824(7) 0.7873(6) 0.9423(5) 0.0598(12) Uani d . 1 . . C H10A 1.0622 0.8238 0.8538 0.090 Uiso calc R 1 . . H H10B 1.0448 0.6893 0.9910 0.090 Uiso calc R 1 . . H H10C 0.9583 0.8683 0.9996 0.090 Uiso calc R 1 . . H C11 0.6925(8) 0.9129(6) 0.8360(5) 0.0659(13) Uani d . 1 . . C H11A 0.5752 0.8924 0.8179 0.099 Uiso calc R 1 . . H H11B 0.7723 0.9502 0.7478 0.099 Uiso calc R 1 . . H H11C 0.6667 0.9937 0.8936 0.099 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 Br1 0.0435(3) 0.0747(4) 0.0942(4) 0.0070(2) -0.0152(2) -0.0390(3) O1 0.0346(15) 0.0580(19) 0.078(2) -0.0006(13) -0.0085(14) -0.0241(16) O2 0.0381(15) 0.0584(18) 0.0578(18) -0.0105(13) -0.0104(13) -0.0042(14) N1 0.0322(16) 0.0492(19) 0.0479(19) -0.0037(14) -0.0022(14) -0.0165(15) C1 0.036(2) 0.044(2) 0.044(2) -0.0096(16) -0.0062(16) -0.0069(17) C2 0.036(2) 0.052(2) 0.048(2) -0.0079(17) -0.0090(17) -0.0148(19) C3 0.036(2) 0.048(2) 0.051(2) -0.0089(17) -0.0046(17) -0.0131(19) C4 0.050(2) 0.051(2) 0.047(2) -0.0118(19) -0.0074(19) -0.0144(19) C5 0.050(2) 0.060(3) 0.057(3) -0.013(2) -0.019(2) -0.015(2) C6 0.039(2) 0.058(3) 0.057(3) -0.0047(18) -0.0153(19) -0.013(2) C7 0.035(2) 0.047(2) 0.048(2) -0.0064(17) -0.0051(17) -0.0073(18) C8 0.046(2) 0.043(2) 0.051(2) -0.0045(17) -0.0026(18) -0.0162(18) C9 0.046(2) 0.053(3) 0.053(3) 0.0008(19) -0.0044(19) -0.017(2) C10 0.057(3) 0.057(3) 0.074(3) -0.020(2) -0.007(2) -0.025(2) C11 0.077(3) 0.046(3) 0.070(3) 0.001(2) -0.009(3) -0.011(2) 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' Br Br -0.2901 2.4595 '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 C9 O2 H2B 109.5 no C7 N1 C8 125.6(3) no C7 N1 H1A 117.2 no C8 N1 H1A 117.2 no C6 C1 C2 118.8(4) no C6 C1 C7 117.8(4) no C2 C1 C7 123.4(3) no C3 C2 C1 118.8(4) no C3 C2 H2A 120.6 no C1 C2 H2A 120.6 no C2 C3 C4 122.7(4) no C2 C3 Br1 118.9(3) no C4 C3 Br1 118.5(3) no C3 C4 C5 117.6(4) no C3 C4 H4A 121.2 no C5 C4 H4A 121.2 no C6 C5 C4 121.0(4) no C6 C5 H5A 119.5 no C4 C5 H5A 119.5 no C5 C6 C1 121.0(4) no C5 C6 H6A 119.5 no C1 C6 H6A 119.5 no O1 C7 N1 122.0(4) no O1 C7 C1 120.1(4) no N1 C7 C1 118.0(3) no N1 C8 C10 106.1(3) no N1 C8 C9 110.5(3) no C10 C8 C9 110.2(4) no N1 C8 C11 111.0(4) no C10 C8 C11 109.9(4) no C9 C8 C11 109.2(4) no O2 C9 C8 111.2(3) no O2 C9 H9A 109.4 no C8 C9 H9A 109.4 no O2 C9 H9B 109.4 no C8 C9 H9B 109.4 no H9A C9 H9B 108.0 no C8 C10 H10A 109.5 no C8 C10 H10B 109.5 no H10A C10 H10B 109.5 no C8 C10 H10C 109.5 no H10A C10 H10C 109.5 no H10B C10 H10C 109.5 no C8 C11 H11A 109.5 no C8 C11 H11B 109.5 no H11A C11 H11B 109.5 no C8 C11 H11C 109.5 no H11A C11 H11C 109.5 no H11B C11 H11C 109.5 no 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 Br1 C3 . 1.904(4) no O1 C7 . 1.239(5) no O2 C9 . 1.411(5) no O2 H2B . 0.8200 no N1 C7 . 1.338(5) no N1 C8 . 1.471(5) no N1 H1A . 0.8600 no C1 C6 . 1.387(5) no C1 C2 . 1.395(5) no C1 C7 . 1.505(6) no C2 C3 . 1.371(6) no C2 H2A . 0.9300 no C3 C4 . 1.378(5) no C4 C5 . 1.384(6) no C4 H4A . 0.9300 no C5 C6 . 1.361(6) no C5 H5A . 0.9300 no C6 H6A . 0.9300 no C8 C10 . 1.533(6) no C8 C9 . 1.534(6) no C8 C11 . 1.540(6) no C9 H9A . 0.9700 no C9 H9B . 0.9700 no C10 H10A . 0.9600 no C10 H10B . 0.9600 no C10 H10C . 0.9600 no C11 H11A . 0.9600 no C11 H11B . 0.9600 no C11 H11C . 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 O2 H2B O1 2_667 0.82 1.92 2.734(4) 169 yes N1 H1A O2 2_767 0.86 2.38 3.173(4) 153 yes C2 H2A O2 2_767 0.93 2.35 3.277(5) 176 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4414795