#------------------------------------------------------------------------------ #$Date: 2023-11-01 19:01:31 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287210 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519461.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4519461 loop_ _publ_author_name 'Abdel Rahman Al Ahmad' 'Thierry Maris' 'Christian Pellerin' 'James D. Wuest' _publ_section_title ; Adding a Pinch of Salt: Using Ionic Mixed-Crystal Seeds to Search for New Solid Forms ; _journal_name_full 'Crystal Growth & Design' _journal_page_first 7472 _journal_page_last 7481 _journal_paper_doi 10.1021/acs.cgd.3c00884 _journal_volume 23 _journal_year 2023 _chemical_formula_moiety 'C12 H14 N2, 0.544(I), 1.456(Br)' _chemical_formula_sum 'C12 H14 Br1.46 I0.54 N2' _chemical_formula_weight 371.92 _chemical_name_common 'Paraquat Iodide Bromide 0.54:1.46' _chemical_name_systematic ; 1,1'-dimethyl-4,4'-bipyridin-1-ium iodide bromide ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _cell_angle_alpha 90 _cell_angle_beta 95.946(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.9640(5) _cell_length_b 8.1119(7) _cell_length_c 13.6647(12) _cell_measurement_reflns_used 4274 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.857 _cell_measurement_theta_min 2.829 _cell_volume 657.53(10) _computing_cell_refinement ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.42 _diffrn_detector_type 'Bruker CMOS Photon III ' _diffrn_measured_fraction_theta_full 0.970 _diffrn_measured_fraction_theta_max 0.956 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Ga K\a' _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_unetI/netI 0.0390 _diffrn_reflns_Laue_measured_fraction_full 0.970 _diffrn_reflns_Laue_measured_fraction_max 0.956 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4610 _diffrn_reflns_point_group_measured_fraction_full 0.970 _diffrn_reflns_point_group_measured_fraction_max 0.956 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 55.124 _diffrn_reflns_theta_min 5.525 _diffrn_source 'Metal Jet' _diffrn_source_current 2.86 _diffrn_source_power 0.19937059999999998 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.71 _exptl_absorpt_coefficient_mu 10.721 _exptl_absorpt_correction_T_max 0.1122 _exptl_absorpt_correction_T_min 0.0108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1559 before and 0.0856 after correction. The Ratio of minimum to maximum transmission is 0.0963. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light orange' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.878 _exptl_crystal_description block _exptl_crystal_F_000 360 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _refine_diff_density_max 1.134 _refine_diff_density_min -0.721 _refine_diff_density_rms 0.153 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 78 _refine_ls_number_reflns 1204 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.127 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0478 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+0.7343P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1275 _refine_ls_wR_factor_ref 0.1305 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1097 _reflns_number_total 1204 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S16_Pq-Br_1_46_I_0_54_P21_c.cif _cod_data_source_block jw25331 _cod_database_code 4519461 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6384(9) 0.8219(7) 0.3623(4) 0.0560(13) Uani 1 1 d . . . . . H1 H 0.593872 0.798009 0.295068 0.067 Uiso 1 1 calc R U . . . N1 N 0.5202(7) 0.7581(5) 0.4329(3) 0.0489(10) Uani 1 1 d . . . . . C2 C 0.8217(9) 0.9207(6) 0.3873(4) 0.0522(13) Uani 1 1 d . . . . . H2 H 0.897992 0.969595 0.336923 0.063 Uiso 1 1 calc R U . . . C3 C 0.8975(9) 0.9502(6) 0.4856(4) 0.0473(11) Uani 1 1 d . . . . . C4 C 0.7722(9) 0.8808(6) 0.5572(4) 0.0522(12) Uani 1 1 d . . . . . H4 H 0.817583 0.898218 0.625100 0.063 Uiso 1 1 calc R U . . . C5 C 0.5859(9) 0.7887(6) 0.5290(4) 0.0512(12) Uani 1 1 d . . . . . H5 H 0.500145 0.745008 0.577737 0.061 Uiso 1 1 calc R U . . . C6 C 0.3221(9) 0.6531(7) 0.4028(4) 0.0562(13) Uani 1 1 d . . . . . H6A H 0.222053 0.710271 0.352404 0.084 Uiso 1 1 calc R U . . . H6B H 0.240569 0.630668 0.460096 0.084 Uiso 1 1 calc R U . . . H6C H 0.372338 0.548930 0.376114 0.084 Uiso 1 1 calc R U . . . Br1 Br 0.8222(18) 0.4105(11) 0.3252(8) 0.0489(8) Uani 0.728(12) 1 d . . P A 1 I1 I 0.833(3) 0.4330(18) 0.3237(13) 0.0489(8) Uani 0.272(12) 1 d . . P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.054(3) 0.062(3) 0.054(3) -0.002(2) 0.016(2) -0.003(2) N1 0.044(2) 0.043(2) 0.060(2) 0.0006(17) 0.0066(17) 0.0034(17) C2 0.044(3) 0.057(3) 0.057(3) 0.004(2) 0.011(2) -0.001(2) C3 0.045(3) 0.041(2) 0.057(3) 0.003(2) 0.010(2) 0.007(2) C4 0.055(3) 0.048(3) 0.055(3) 0.006(2) 0.010(2) 0.001(2) C5 0.049(3) 0.047(3) 0.057(3) 0.005(2) 0.006(2) 0.000(2) C6 0.045(3) 0.050(3) 0.074(3) -0.004(3) 0.009(2) -0.009(2) Br1 0.0483(10) 0.045(2) 0.0546(5) 0.0014(13) 0.0122(5) -0.0042(13) I1 0.0483(10) 0.045(2) 0.0546(5) 0.0014(13) 0.0122(5) -0.0042(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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' Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I 0.0030 5.4350 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0241 0.0134 '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_site_symmetry_1 _geom_angle_site_symmetry_3 N1 C1 H1 119.7 . . N1 C1 C2 120.5(5) . . C2 C1 H1 119.7 . . C1 N1 C6 118.8(5) . . C5 N1 C1 120.0(4) . . C5 N1 C6 121.2(4) . . C1 C2 H2 119.6 . . C1 C2 C3 120.8(5) . . C3 C2 H2 119.6 . . C2 C3 C3 121.7(6) . 3_776 C2 C3 C4 117.3(5) . . C4 C3 C3 121.1(6) . 3_776 C3 C4 H4 120.0 . . C5 C4 C3 119.9(5) . . C5 C4 H4 120.0 . . N1 C5 C4 121.5(5) . . N1 C5 H5 119.3 . . C4 C5 H5 119.3 . . N1 C6 H6A 109.5 . . N1 C6 H6B 109.5 . . N1 C6 H6C 109.5 . . H6A C6 H6B 109.5 . . H6A C6 H6C 109.5 . . H6B C6 H6C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 H1 0.9500 . C1 N1 1.355(7) . C1 C2 1.369(8) . N1 C5 1.354(6) . N1 C6 1.479(7) . C2 H2 0.9500 . C2 C3 1.394(8) . C3 C3 1.484(11) 3_776 C3 C4 1.408(7) . C4 H4 0.9500 . C4 C5 1.361(8) . C5 H5 0.9500 . C6 H6A 0.9800 . C6 H6B 0.9800 . C6 H6C 0.9800 . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 -1.1(7) . . . . C1 C2 C3 C3 176.9(6) . . . 3_776 C1 C2 C3 C4 -2.8(7) . . . . N1 C1 C2 C3 3.5(8) . . . . C2 C1 N1 C5 -1.5(8) . . . . C2 C1 N1 C6 179.5(5) . . . . C2 C3 C4 C5 0.3(7) . . . . C3 C3 C4 C5 -179.4(5) 3_776 . . . C3 C4 C5 N1 1.7(8) . . . . C6 N1 C5 C4 177.9(5) . . . . _cod_database_fobs_code 4519461