#------------------------------------------------------------------------------ #$Date: 2023-11-01 19:02:46 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287211 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519462.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_4519462 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, 0.362(I), 1.638(Br)' _chemical_formula_sum 'C12 H14 Br1.64 I0.36 N2' _chemical_formula_weight 362.99 _chemical_name_common 'Paraquat Iodide Bromide 0.36:1.64' _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 96.045(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.9498(4) _cell_length_b 8.0945(6) _cell_length_c 13.5611(10) _cell_measurement_reflns_used 4663 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.840 _cell_measurement_theta_min 2.852 _cell_volume 649.48(8) _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 0.985 _diffrn_measured_fraction_theta_max 0.977 _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 0.0332 _diffrn_reflns_av_unetI/netI 0.0258 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5522 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.822 _diffrn_reflns_theta_min 5.546 _diffrn_source 'Metal Jet' _diffrn_source_current 2.85 _diffrn_source_power 0.198759 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.74 _exptl_absorpt_coefficient_mu 8.870 _exptl_absorpt_correction_T_max 0.1123 _exptl_absorpt_correction_T_min 0.0336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0974 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.2992. 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 1.856 _exptl_crystal_description Fragment _exptl_crystal_F_000 353 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.389 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.061 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 78 _refine_ls_number_reflns 1206 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.091 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0232 _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^)+(0.0221P)^2^+0.5465P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.0610 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1107 _reflns_number_total 1206 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S17_Pq-Br_1_64_I_0_36_P21_c.cif _cod_data_source_block jw25421 _cod_database_code 4519462 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 Br1 Br 0.8267(8) 0.5865(5) 0.3262(3) 0.0453(3) Uani 0.819(7) 1 d . . P A 1 I1 I 0.822(2) 0.5679(14) 0.3192(10) 0.0453(3) Uani 0.181(7) 1 d . . P A 2 C1 C 0.6372(5) 0.1796(4) 0.3622(2) 0.0479(7) Uani 1 1 d . . . . . H1 H 0.591330 0.203360 0.294463 0.058 Uiso 1 1 calc R U . . . N1 N 0.5195(4) 0.2420(3) 0.43254(18) 0.0430(6) Uani 1 1 d . . . . . C2 C 0.8230(5) 0.0817(3) 0.3867(2) 0.0471(7) Uani 1 1 d . . . . . H2 H 0.900741 0.034798 0.335751 0.057 Uiso 1 1 calc R U . . . C3 C 0.8984(5) 0.0507(3) 0.4856(2) 0.0409(6) Uani 1 1 d . . . . . C4 C 0.7720(5) 0.1186(4) 0.5573(2) 0.0454(7) Uani 1 1 d . . . . . H4 H 0.816544 0.100003 0.625754 0.054 Uiso 1 1 calc R U . . . C5 C 0.5841(5) 0.2118(3) 0.5286(2) 0.0458(7) Uani 1 1 d . . . . . H5 H 0.498037 0.255811 0.577613 0.055 Uiso 1 1 calc R U . . . C6 C 0.3209(5) 0.3489(4) 0.4025(2) 0.0494(7) Uani 1 1 d . . . . . H6A H 0.372263 0.453523 0.376281 0.074 Uiso 1 1 calc R U . . . H6B H 0.239282 0.370802 0.460259 0.074 Uiso 1 1 calc R U . . . H6C H 0.220285 0.292780 0.351267 0.074 Uiso 1 1 calc R U . . . 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 Br1 0.0420(3) 0.0469(9) 0.0482(7) -0.0031(5) 0.0111(4) 0.0007(6) I1 0.0420(3) 0.0469(9) 0.0482(7) -0.0031(5) 0.0111(4) 0.0007(6) C1 0.0448(17) 0.0539(17) 0.0459(16) 0.0020(12) 0.0089(12) 0.0002(13) N1 0.0374(12) 0.0407(12) 0.0514(13) 0.0005(10) 0.0067(10) -0.0027(10) C2 0.0397(16) 0.0562(17) 0.0466(16) -0.0016(12) 0.0101(12) 0.0001(12) C3 0.0383(15) 0.0401(14) 0.0449(15) -0.0020(11) 0.0078(12) -0.0074(11) C4 0.0454(16) 0.0476(15) 0.0432(15) -0.0030(12) 0.0057(12) 0.0010(12) C5 0.0433(16) 0.0450(15) 0.0499(16) -0.0041(12) 0.0089(12) 0.0008(12) C6 0.0418(16) 0.0499(16) 0.0566(18) 0.0020(13) 0.0054(13) 0.0035(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 119.6 . . N1 C1 C2 120.9(3) . . C2 C1 H1 119.6 . . C1 N1 C5 120.3(3) . . C1 N1 C6 119.0(2) . . C5 N1 C6 120.7(2) . . C1 C2 H2 119.8 . . C1 C2 C3 120.5(3) . . C3 C2 H2 119.8 . . C2 C3 C3 121.7(3) . 3_756 C2 C3 C4 117.1(3) . . C4 C3 C3 121.2(3) . 3_756 C3 C4 H4 120.0 . . C5 C4 C3 120.0(3) . . C5 C4 H4 120.0 . . N1 C5 C4 121.2(3) . . N1 C5 H5 119.4 . . C4 C5 H5 119.4 . . 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 1.340(4) . C1 C2 1.372(4) . N1 C5 1.341(4) . N1 C6 1.486(4) . C2 H2 0.9500 . C2 C3 1.392(4) . C3 C3 1.479(6) 3_756 C3 C4 1.403(4) . C4 H4 0.9500 . C4 C5 1.371(4) . C5 H5 0.9500 . C6 H6A 0.9800 . C6 H6B 0.9800 . C6 H6C 0.9800 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C6 H6A Br1 0.98 3.05 3.806(6) 134.7 . yes C6 H6A I1 0.98 3.01 3.745(14) 132.7 . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 0.7(4) . . . . C1 C2 C3 C3 -178.4(3) . . . 3_756 C1 C2 C3 C4 2.2(4) . . . . N1 C1 C2 C3 -2.6(4) . . . . C2 C1 N1 C5 1.1(4) . . . . C2 C1 N1 C6 179.3(3) . . . . C2 C3 C4 C5 -0.4(4) . . . . C3 C3 C4 C5 -179.8(3) 3_756 . . . C3 C4 C5 N1 -1.0(4) . . . . C6 N1 C5 C4 -177.5(3) . . . . _cod_database_fobs_code 4519462