#------------------------------------------------------------------------------ #$Date: 2023-11-01 19:16:54 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287219 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519470.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_4519470 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, 1.854(Br), 0.146(Cl)' _chemical_formula_sum 'C12 H14 Br1.85 Cl0.15 N2' _chemical_formula_weight 339.62 _chemical_name_common ; Paraquat Bromide Chloride 1.85:0.15 ; _chemical_name_systematic ; 1,1'-dimethyl-4,4'-bipyridin-1-ium bromide chloride ; _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 difmap _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 96.173(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.9125(2) _cell_length_b 8.0749(3) _cell_length_c 13.4343(6) _cell_measurement_reflns_used 5041 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.859 _cell_measurement_theta_min 2.879 _cell_volume 637.67(4) _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 0.991 _diffrn_measured_fraction_theta_max 0.988 _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 0.0230 _diffrn_reflns_av_unetI/netI 0.0175 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.988 _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 -16 _diffrn_reflns_number 5857 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.845 _diffrn_reflns_theta_min 5.570 _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 5.037 _exptl_absorpt_correction_T_max 0.1123 _exptl_absorpt_correction_T_min 0.0312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0991 before and 0.0497 after correction. The Ratio of minimum to maximum transmission is 0.2778. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.769 _exptl_crystal_description Block _exptl_crystal_F_000 335 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.272 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 105 _refine_ls_number_reflns 1195 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.107 _refine_ls_R_factor_all 0.0187 _refine_ls_R_factor_gt 0.0176 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0306P)^2^+0.1638P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.0531 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1132 _reflns_number_total 1195 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S27_Pq-Br_1_85_Cl_0_15_P21_c.cif _cod_data_source_block jw25471 _cod_database_code 4519470 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 0.8241(2) 0.58311(17) 0.32402(6) 0.03848(15) Uani 0.927(5) 1 d . . P A 1 Cl1 Cl 0.827(7) 0.581(5) 0.338(2) 0.03848(15) Uani 0.073(5) 1 d . . P A 2 C1 C 0.6377(3) 0.1823(2) 0.36057(13) 0.0395(4) Uani 1 1 d . . . . . H1 H 0.570(4) 0.208(3) 0.2944(17) 0.043(5) Uiso 1 1 d . . . . . N1 N 0.5178(3) 0.24439(18) 0.43185(11) 0.0363(4) Uani 1 1 d . . . . . C2 C 0.8245(4) 0.0844(2) 0.38537(15) 0.0398(5) Uani 1 1 d . . . . . H2 H 0.907(5) 0.042(3) 0.3346(18) 0.053(6) Uiso 1 1 d . . . . . C3 C 0.8973(3) 0.0508(2) 0.48562(14) 0.0353(4) Uani 1 1 d . . . . . C4 C 0.7693(3) 0.1178(2) 0.55786(14) 0.0379(4) Uani 1 1 d . . . . . H4 H 0.814(4) 0.095(2) 0.6267(18) 0.045(6) Uiso 1 1 d . . . . . C5 C 0.5814(3) 0.2118(2) 0.52924(14) 0.0384(4) Uani 1 1 d . . . . . H5 H 0.484(4) 0.253(3) 0.5754(17) 0.044(6) Uiso 1 1 d . . . . . C6 C 0.3183(3) 0.3518(3) 0.40178(16) 0.0417(5) Uani 1 1 d . . . . . H6A H 0.365(5) 0.451(3) 0.374(2) 0.066(8) Uiso 1 1 d . . . . . H6B H 0.219(4) 0.293(3) 0.3475(18) 0.050(6) Uiso 1 1 d . . . . . H6C H 0.228(4) 0.374(3) 0.4598(19) 0.054(6) Uiso 1 1 d . . . . . 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 0.03728(16) 0.04458(17) 0.0345(3) 0.0005(3) 0.0079(2) 0.00233(8) Cl1 0.03728(16) 0.04458(17) 0.0345(3) 0.0005(3) 0.0079(2) 0.00233(8) C1 0.0391(10) 0.0455(10) 0.0342(9) 0.0027(8) 0.0055(7) -0.0002(8) N1 0.0339(8) 0.0360(8) 0.0394(8) -0.0007(6) 0.0052(6) -0.0030(6) C2 0.0365(10) 0.0473(11) 0.0366(10) -0.0004(7) 0.0087(8) -0.0003(7) C3 0.0348(10) 0.0351(8) 0.0368(9) -0.0004(7) 0.0068(7) -0.0053(7) C4 0.0404(11) 0.0403(9) 0.0334(9) -0.0023(7) 0.0052(7) -0.0010(8) C5 0.0391(10) 0.0391(9) 0.0376(9) -0.0039(7) 0.0072(7) -0.0016(7) C6 0.0382(10) 0.0421(11) 0.0448(11) 0.0011(9) 0.0045(8) 0.0034(8) 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' Cl Cl 0.3281 0.5435 '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 112.4(13) . . N1 C1 C2 120.91(17) . . C2 C1 H1 126.5(13) . . C1 N1 C6 119.14(16) . . C5 N1 C1 120.27(16) . . C5 N1 C6 120.58(15) . . C1 C2 H2 120.0(16) . . C1 C2 C3 120.24(18) . . C3 C2 H2 119.7(16) . . C2 C3 C3 121.2(2) . 3_756 C2 C3 C4 117.37(18) . . C4 C3 C3 121.4(2) . 3_756 C3 C4 H4 119.2(14) . . C5 C4 C3 120.19(18) . . C5 C4 H4 120.6(14) . . N1 C5 C4 121.00(17) . . N1 C5 H5 116.1(13) . . C4 C5 H5 122.8(13) . . N1 C6 H6A 110.4(18) . . N1 C6 H6B 107.6(13) . . N1 C6 H6C 111.5(14) . . H6A C6 H6B 107(2) . . H6A C6 H6C 111(2) . . H6B C6 H6C 109.4(19) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 H1 0.96(2) . C1 N1 1.348(2) . C1 C2 1.370(3) . N1 C5 1.348(2) . N1 C6 1.484(2) . C2 H2 0.95(3) . C2 C3 1.396(3) . C3 C3 1.482(4) 3_756 C3 C4 1.402(3) . C4 H4 0.95(2) . C4 C5 1.367(3) . C5 H5 0.95(2) . C6 H6A 0.94(3) . C6 H6B 1.01(2) . C6 H6C 1.01(3) . 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 0.9(3) . . . . C1 C2 C3 C3 -178.2(2) . . . 3_756 C1 C2 C3 C4 1.4(3) . . . . N1 C1 C2 C3 -1.7(3) . . . . C2 C1 N1 C5 0.5(3) . . . . C2 C1 N1 C6 179.19(18) . . . . C2 C3 C4 C5 0.0(3) . . . . C3 C3 C4 C5 179.7(2) 3_756 . . . C3 C4 C5 N1 -1.2(3) . . . . C6 N1 C5 C4 -177.71(17) . . . . _cod_database_fobs_code 4519470