#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206875.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_2206875 loop_ _publ_author_name 'Ronaldson, Vicki' 'Storey, John. M. D.' 'Harrison, William T. A.' _publ_section_title ; N-(2-Bromophenyl)propionamide ; _journal_coeditor_code BT6731 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3200 _journal_page_last o3202 _journal_paper_doi 10.1107/S1600536805027935 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C9 H10 Br N O' _chemical_formula_moiety 'C9 H10 Br N O' _chemical_formula_sum 'C9 H10 Br N O' _chemical_formula_weight 228.09 _chemical_name_systematic ; N-(2-Bromophenyl)propionamide ; _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' _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 93.964(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.87010(10) _cell_length_b 11.8048(4) _cell_length_c 15.9296(5) _cell_measurement_reflns_used 2165 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 913.61(5) _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction 'SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f' _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 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 13742 _diffrn_reflns_theta_full 27.54 _diffrn_reflns_theta_max 27.54 _diffrn_reflns_theta_min 3.09 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 4.449 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_correction_T_min 0.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.383 _refine_diff_density_min -0.370 _refine_ls_extinction_coef 0.0039(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 114 _refine_ls_number_reflns 2092 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0269 _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^)+(0.0226P)^2^+0.9463P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.0648 _reflns_number_gt 1822 _reflns_number_total 2092 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6731.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2206875 _cod_database_fobs_code 2206875 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 C1 0.4616(5) 0.54914(19) 0.20494(14) 0.0194(5) Uani d . 1 C C2 0.5180(5) 0.6609(2) 0.22655(15) 0.0237(5) Uani d . 1 C H2 0.4342 0.6949 0.2724 0.028 Uiso calc R 1 H C3 0.6975(5) 0.7226(2) 0.18071(16) 0.0273(5) Uani d . 1 C H3 0.7417 0.7985 0.1960 0.033 Uiso calc R 1 H C4 0.8129(5) 0.6731(2) 0.11218(16) 0.0260(5) Uani d . 1 C H4 0.9370 0.7153 0.0809 0.031 Uiso calc R 1 H C5 0.7481(5) 0.5631(2) 0.08939(15) 0.0236(5) Uani d . 1 C H5 0.8228 0.5311 0.0412 0.028 Uiso calc R 1 H C6 0.5740(4) 0.4983(2) 0.13620(14) 0.0186(5) Uani d . 1 C C7 0.6917(4) 0.3057(2) 0.09094(13) 0.0186(5) Uani d . 1 C C8 0.5718(5) 0.1890(2) 0.07664(16) 0.0238(5) Uani d . 1 C H8A 0.4053 0.1950 0.0376 0.029 Uiso calc R 1 H H8B 0.5139 0.1594 0.1308 0.029 Uiso calc R 1 H C9 0.7679(5) 0.1053(2) 0.04102(19) 0.0334(6) Uani d . 1 C H9A 0.6908 0.0288 0.0435 0.050 Uiso calc R 1 H H9B 0.9451 0.1080 0.0741 0.050 Uiso calc R 1 H H9C 0.7949 0.1249 -0.0176 0.050 Uiso calc R 1 H N1 0.5104(4) 0.38443(17) 0.11491(12) 0.0199(4) Uani d . 1 N H1 0.342(6) 0.367(2) 0.1167(16) 0.024 Uiso d . 1 H O1 0.9361(3) 0.32624(14) 0.08417(11) 0.0241(4) Uani d . 1 O Br1 0.23270(5) 0.46366(2) 0.273034(14) 0.02474(11) Uani d . 1 Br 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 0.0135(10) 0.0232(12) 0.0217(11) -0.0002(9) 0.0026(8) 0.0011(9) C2 0.0237(12) 0.0234(12) 0.0243(12) 0.0024(9) 0.0030(9) -0.0022(10) C3 0.0258(13) 0.0202(12) 0.0357(14) -0.0008(10) 0.0011(10) -0.0007(11) C4 0.0195(12) 0.0277(13) 0.0311(13) -0.0039(10) 0.0034(10) 0.0064(10) C5 0.0195(12) 0.0279(13) 0.0242(12) 0.0007(9) 0.0064(9) 0.0003(10) C6 0.0138(10) 0.0211(11) 0.0205(11) 0.0014(9) -0.0008(9) 0.0013(9) C7 0.0162(11) 0.0244(12) 0.0152(10) -0.0014(9) 0.0017(8) -0.0003(9) C8 0.0149(11) 0.0229(12) 0.0336(13) -0.0034(9) 0.0019(9) -0.0025(10) C9 0.0265(13) 0.0269(13) 0.0472(16) -0.0046(11) 0.0046(12) -0.0115(12) N1 0.0119(9) 0.0239(10) 0.0242(10) -0.0033(8) 0.0038(7) -0.0028(8) O1 0.0142(8) 0.0249(9) 0.0334(9) -0.0022(6) 0.0043(7) -0.0052(7) Br1 0.02460(16) 0.02600(15) 0.02478(16) -0.00150(9) 0.01004(10) -0.00078(10) 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 C2 C1 C6 121.5(2) C2 C1 Br1 118.57(17) C6 C1 Br1 119.90(17) C3 C2 C1 119.4(2) C3 C2 H2 120.3 C1 C2 H2 120.3 C2 C3 C4 119.9(2) C2 C3 H3 120.1 C4 C3 H3 120.1 C5 C4 C3 120.3(2) C5 C4 H4 119.9 C3 C4 H4 119.9 C4 C5 C6 120.8(2) C4 C5 H5 119.6 C6 C5 H5 119.6 C1 C6 C5 118.1(2) C1 C6 N1 120.4(2) C5 C6 N1 121.6(2) O1 C7 N1 122.9(2) O1 C7 C8 122.4(2) N1 C7 C8 114.60(19) C7 C8 C9 113.92(19) C7 C8 H8A 108.8 C9 C8 H8A 108.8 C7 C8 H8B 108.8 C9 C8 H8B 108.8 H8A C8 H8B 107.7 C8 C9 H9A 109.5 C8 C9 H9B 109.5 H9A C9 H9B 109.5 C8 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C7 N1 C6 125.68(19) C7 N1 H1 119.4(18) C6 N1 H1 114.9(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.386(3) C1 C6 1.393(3) C1 Br1 1.899(2) C2 C3 1.384(3) C2 H2 0.9500 C3 C4 1.390(4) C3 H3 0.9500 C4 C5 1.379(3) C4 H4 0.9500 C5 C6 1.395(3) C5 H5 0.9500 C6 N1 1.416(3) C7 O1 1.227(3) C7 N1 1.355(3) C7 C8 1.507(3) C8 C9 1.512(3) C8 H8A 0.9900 C8 H8B 0.9900 C9 H9A 0.9800 C9 H9B 0.9800 C9 H9C 0.9800 N1 H1 0.85(3) 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 N1 H1 O1 1_455 0.85(3) 2.06(3) 2.889(2) 164(2) 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 C6 C1 C2 C3 -2.3(4) Br1 C1 C2 C3 176.17(18) C1 C2 C3 C4 1.9(4) C2 C3 C4 C5 0.4(4) C3 C4 C5 C6 -2.3(4) C2 C1 C6 C5 0.4(4) Br1 C1 C6 C5 -178.01(17) C2 C1 C6 N1 -179.3(2) Br1 C1 C6 N1 2.3(3) C4 C5 C6 C1 1.9(4) C4 C5 C6 N1 -178.5(2) O1 C7 C8 C9 -8.7(3) N1 C7 C8 C9 173.8(2) O1 C7 N1 C6 -0.9(4) C8 C7 N1 C6 176.7(2) C1 C6 N1 C7 -138.0(2) C5 C6 N1 C7 42.4(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 806861 2 PubChem 924969