#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204990.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_2204990 loop_ _publ_author_name 'Cheng, Bi Yun' 'Zeng, Jing Yao' 'Chiu, Pei Ling' 'Lee, Hon Man' _publ_section_title ; 1-(6-Bromopyridin-2-yl)-3-methyl-3H-imidazol-1-ium bromide monohydrate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o509 _journal_page_last o510 _journal_paper_doi 10.1107/S1600536805002783 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C9 H9 Br N3 +, Br -, H2 O' _chemical_formula_moiety 'C9 H9 Br N3 +, Br -, H2 O' _chemical_formula_sum 'C9 H11 Br2 N3 O' _chemical_formula_weight 337.03 _chemical_name_systematic ; 1-(6-Bromopyridin-2-yl)-3-methyl-3H-imidzol-1-ium bromide monoydrate ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 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 7.1233(3) _cell_length_b 17.3399(7) _cell_length_c 9.5533(4) _cell_measurement_reflns_used 4258 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.8 _cell_measurement_theta_min 2.3 _cell_volume 1180.00(8) _computing_cell_refinement 'APEX2 and SAINT' _computing_data_collection 'APEX2 (Bruker, 2004) and SMART (Bruker, 2004)' _computing_data_reduction APEX2 _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART APEX-II' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0603 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 11417 _diffrn_reflns_theta_full 28.73 _diffrn_reflns_theta_max 28.73 _diffrn_reflns_theta_min 2.35 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 6.848 _exptl_absorpt_correction_T_max 0.334 _exptl_absorpt_correction_T_min 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.843 _refine_diff_density_min -0.636 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.042(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 2877 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0346 _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^)+(0.0545P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0914 _refine_ls_wR_factor_ref 0.0971 _reflns_number_gt 2522 _reflns_number_total 2877 _reflns_threshold_expression I>2\s _cod_data_source_file ac6155.cif _cod_data_source_block I _cod_database_code 2204990 _cod_database_fobs_code 2204990 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, 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 Br1 0.30233(6) 0.19841(3) -0.23207(5) 0.02620(13) Uani d . 1 Br Br2 0.13404(6) 0.07940(3) 0.50740(6) 0.02505(13) Uani d . 1 Br C1 0.5194(6) 0.1122(3) 0.2560(6) 0.0223(9) Uani d . 1 C H1 0.4801 0.0842 0.1756 0.027 Uiso calc R 1 H C2 0.6288(6) 0.1404(3) 0.4649(5) 0.0237(11) Uani d . 1 C H2 0.6796 0.1343 0.5562 0.028 Uiso calc R 1 H C3 0.5812(7) 0.2072(3) 0.4043(6) 0.0259(11) Uani d . 1 C H3 0.5926 0.2573 0.4436 0.031 Uiso calc R 1 H C4 0.6190(9) -0.0011(3) 0.3931(7) 0.0352(13) Uani d . 1 C H4A 0.5138 -0.0220 0.4473 0.053 Uiso calc R 1 H H4B 0.7364 -0.0096 0.4443 0.053 Uiso calc R 1 H H4C 0.6254 -0.0272 0.3022 0.053 Uiso calc R 1 H C5 0.4580(6) 0.2409(3) 0.1619(5) 0.0183(9) Uani d . 1 C C6 0.4615(6) 0.3201(3) 0.1818(6) 0.0235(10) Uani d . 1 C H6 0.4980 0.3425 0.2684 0.028 Uiso calc R 1 H C7 0.4083(7) 0.3653(3) 0.0668(6) 0.0266(11) Uani d . 1 C H7 0.4064 0.4199 0.0740 0.032 Uiso calc R 1 H C8 0.3583(7) 0.3296(3) -0.0574(6) 0.0264(11) Uani d . 1 C H8 0.3216 0.3592 -0.1365 0.032 Uiso calc R 1 H C9 0.3632(6) 0.2503(3) -0.0637(6) 0.0208(10) Uani d . 1 C H10 0.101(11) -0.028(4) 0.177(9) 0.05(2) Uiso d . 1 H H11 0.166(10) 0.009(4) 0.294(11) 0.06(2) Uiso d . 1 H N1 0.5912(6) 0.0821(2) 0.3714(5) 0.0223(9) Uani d . 1 N N2 0.5116(5) 0.1888(2) 0.2721(5) 0.0189(7) Uani d . 1 N N3 0.4096(5) 0.2052(2) 0.0429(4) 0.0185(8) Uani d . 1 N O1 0.2111(5) -0.0199(2) 0.2153(4) 0.0311(9) Uani d . 1 O 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 0.0303(2) 0.0300(2) 0.0183(2) 0.00259(19) -0.0024(2) -0.0006(2) Br2 0.0293(2) 0.0249(2) 0.0210(2) -0.00332(18) 0.0014(2) 0.0006(2) C1 0.023(2) 0.027(2) 0.017(2) -0.0031(17) -0.001(2) 0.003(2) C2 0.023(2) 0.029(3) 0.020(3) -0.0007(19) -0.0023(17) -0.004(2) C3 0.021(2) 0.038(3) 0.019(3) 0.001(2) -0.0017(18) -0.002(2) C4 0.045(3) 0.030(3) 0.031(3) 0.001(2) -0.009(2) 0.007(3) C5 0.017(2) 0.023(2) 0.016(2) -0.0013(17) 0.0013(16) 0.0020(19) C6 0.021(2) 0.022(2) 0.027(3) 0.0003(18) 0.0015(19) -0.002(2) C7 0.029(3) 0.022(2) 0.029(3) 0.004(2) 0.002(2) 0.002(2) C8 0.030(3) 0.022(3) 0.027(3) 0.005(2) 0.000(2) 0.006(2) C9 0.019(2) 0.026(3) 0.017(2) -0.0016(19) 0.0010(17) -0.0043(19) N1 0.0242(19) 0.026(2) 0.016(2) 0.0031(16) -0.0027(16) 0.0007(18) N2 0.0193(15) 0.0212(16) 0.0163(18) 0.0005(13) 0.0011(18) -0.0001(18) N3 0.0168(16) 0.0197(18) 0.019(2) 0.0008(14) 0.0006(14) 0.0008(16) O1 0.032(2) 0.037(2) 0.025(2) 0.0001(17) -0.0022(16) -0.0055(17) 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 N1 C1 N2 108.1(5) N1 C1 H1 125.9 N2 C1 H1 125.9 C3 C2 N1 107.8(4) C3 C2 H2 126.1 N1 C2 H2 126.1 C2 C3 N2 106.4(5) C2 C3 H3 126.8 N2 C3 H3 126.8 N1 C4 H4A 109.5 N1 C4 H4B 109.5 H4A C4 H4B 109.5 N1 C4 H4C 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 N3 C5 C6 125.4(4) N3 C5 N2 113.5(4) C6 C5 N2 121.1(4) C5 C6 C7 116.2(5) C5 C6 H6 121.9 C7 C6 H6 121.9 C8 C7 C6 119.5(5) C8 C7 H7 120.2 C6 C7 H7 120.2 C9 C8 C7 118.5(5) C9 C8 H8 120.8 C7 C8 H8 120.8 N3 C9 C8 124.2(5) N3 C9 Br1 115.5(4) C8 C9 Br1 120.4(4) C1 N1 C2 109.1(4) C1 N1 C4 123.8(5) C2 N1 C4 127.1(4) C1 N2 C3 108.5(4) C1 N2 C5 123.4(5) C3 N2 C5 127.8(4) C9 N3 C5 116.3(4) H10 O1 H11 96(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C9 1.893(5) C1 N1 1.323(7) C1 N2 1.338(5) C1 H1 0.9500 C2 C3 1.339(8) C2 N1 1.375(7) C2 H2 0.9500 C3 N2 1.394(7) C3 H3 0.9500 C4 N1 1.472(7) C4 H4A 0.9800 C4 H4B 0.9800 C4 H4C 0.9800 C5 N3 1.339(6) C5 C6 1.386(6) C5 N2 1.440(6) C6 C7 1.401(7) C6 H6 0.9500 C7 C8 1.384(8) C7 H7 0.9500 C8 C9 1.378(7) C8 H8 0.9500 C9 N3 1.326(7) O1 H10 0.88(8) O1 H11 0.96(10) 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 H11 Br2 . 0.96(10) 2.38(10) 3.324(4) 165(6) C1 H1 O1 . 0.95 2.66 3.196(6) 116 C3 H3 Br2 3 0.95 2.91 3.847(6) 168 C6 H6 Br2 3 0.95 2.83 3.771(5) 173 C8 H8 O1 4_554 0.95 2.54 3.431(7) 156 C7 H7 Br2 4_554 0.95 2.85 3.768(5) 162 C4 H4B O1 2_655 0.98 2.66 3.327(8) 125 C2 H2 O1 2_655 0.95 2.62 3.375(6) 136 C4 H4C Br1 2_655 0.98 3.03 3.667(6) 124 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21130033 2 PubChem 139067364