#------------------------------------------------------------------------------ #$Date: 2023-11-01 18:55:18 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287207 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519458.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_4519458 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, 1.208(I), 0.792(Br)' _chemical_formula_sum 'C12 H14 Br0.79 I1.21 N2' _chemical_formula_weight 402.93 _chemical_name_common 'Paraquat Iodide Bromide 1.21:0.79' _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 95.912(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.0357(3) _cell_length_b 8.1410(3) _cell_length_c 13.9228(6) _cell_measurement_reflns_used 5132 _cell_measurement_temperature 150 _cell_measurement_theta_max 55.009 _cell_measurement_theta_min 2.777 _cell_volume 680.48(5) _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 0.993 _diffrn_measured_fraction_theta_max 0.991 _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 0.0312 _diffrn_reflns_av_unetI/netI 0.0226 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.991 _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 6322 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.984 _diffrn_reflns_theta_min 5.484 _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 16.939 _exptl_absorpt_correction_T_max 0.1122 _exptl_absorpt_correction_T_min 0.0328 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1114 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.2923. 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 1.966 _exptl_crystal_description Block _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.510 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.070 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 78 _refine_ls_number_reflns 1293 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0209 _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^)+(0.0222P)^2^+0.5117P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.0532 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1184 _reflns_number_total 1293 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S12_Pq-Br_0_79_I_1_21_P21_c.cif _cod_data_source_block jw25373 _cod_database_code 4519458 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 I1 I 0.8337(7) 0.4236(6) 0.3263(3) 0.0434(3) Uani 0.604(8) 1 d . . P A 1 Br1 Br 0.8158(18) 0.4152(15) 0.3204(8) 0.0434(3) Uani 0.396(8) 1 d . . P A 2 N1 N 0.5232(4) 0.7637(3) 0.43448(18) 0.0439(6) Uani 1 1 d . . . . . C1 C 0.6373(5) 0.8278(4) 0.3655(2) 0.0492(8) Uani 1 1 d . . . . . H1 H 0.589552 0.807111 0.299490 0.059 Uiso 1 1 calc R U . . . C2 C 0.8227(5) 0.9234(4) 0.3898(2) 0.0476(8) Uani 1 1 d . . . . . H2 H 0.899557 0.970697 0.340423 0.057 Uiso 1 1 calc R U . . . C3 C 0.8981(5) 0.9510(3) 0.4859(2) 0.0410(7) Uani 1 1 d . . . . . C4 C 0.7758(5) 0.8816(4) 0.5560(2) 0.0469(7) Uani 1 1 d . . . . . H4 H 0.821740 0.898178 0.622599 0.056 Uiso 1 1 calc R U . . . C5 C 0.5899(5) 0.7898(4) 0.5283(2) 0.0453(7) Uani 1 1 d . . . . . H5 H 0.506938 0.743987 0.576170 0.054 Uiso 1 1 calc R U . . . C6 C 0.3260(5) 0.6589(4) 0.4054(2) 0.0502(8) Uani 1 1 d . . . . . H6A H 0.227646 0.715399 0.355584 0.075 Uiso 1 1 calc R U . . . H6B H 0.245163 0.637907 0.461732 0.075 Uiso 1 1 calc R U . . . H6C H 0.375074 0.554434 0.379831 0.075 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 I1 0.0388(7) 0.0477(5) 0.0448(6) -0.0006(4) 0.0087(4) -0.0027(4) Br1 0.0388(7) 0.0477(5) 0.0448(6) -0.0006(4) 0.0087(4) -0.0027(4) N1 0.0373(13) 0.0398(13) 0.0550(15) -0.0007(11) 0.0068(10) 0.0040(10) C1 0.0442(17) 0.0566(19) 0.0473(17) -0.0043(14) 0.0077(13) 0.0010(14) C2 0.0427(17) 0.0563(19) 0.0453(17) 0.0012(13) 0.0116(13) 0.0003(13) C3 0.0366(15) 0.0393(15) 0.0478(16) -0.0006(12) 0.0077(12) 0.0075(12) C4 0.0460(17) 0.0468(16) 0.0485(17) 0.0029(13) 0.0082(13) 0.0009(13) C5 0.0424(16) 0.0448(16) 0.0494(17) 0.0052(13) 0.0076(12) 0.0007(13) C6 0.0413(17) 0.0491(18) 0.0608(19) -0.0012(15) 0.0074(14) -0.0033(14) 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 C1 N1 C5 120.6(3) . . C1 N1 C6 118.9(3) . . C5 N1 C6 120.4(3) . . N1 C1 H1 119.7 . . N1 C1 C2 120.5(3) . . C2 C1 H1 119.7 . . C1 C2 H2 119.8 . . C1 C2 C3 120.4(3) . . C3 C2 H2 119.8 . . C2 C3 C3 121.5(3) . 3_776 C2 C3 C4 117.5(3) . . C4 C3 C3 120.9(3) . 3_776 C3 C4 H4 120.0 . . C5 C4 C3 119.9(3) . . C5 C4 H4 120.0 . . N1 C5 C4 121.0(3) . . N1 C5 H5 119.5 . . C4 C5 H5 119.5 . . 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 N1 C1 1.343(4) . N1 C5 1.344(4) . N1 C6 1.486(4) . C1 H1 0.9500 . C1 C2 1.376(4) . C2 H2 0.9500 . C2 C3 1.386(4) . C3 C3 1.485(6) 3_776 C3 C4 1.402(4) . C4 H4 0.9500 . C4 C5 1.370(4) . 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 N1 C1 C2 C3 1.8(5) . . . . C1 N1 C5 C4 -0.3(4) . . . . C1 C2 C3 C3 178.0(3) . . . 3_776 C1 C2 C3 C4 -1.5(4) . . . . C2 C3 C4 C5 0.3(4) . . . . C3 C3 C4 C5 -179.1(3) 3_776 . . . C3 C4 C5 N1 0.6(5) . . . . C5 N1 C1 C2 -0.9(4) . . . . C6 N1 C1 C2 -179.0(3) . . . . C6 N1 C5 C4 177.8(3) . . . . _cod_database_fobs_code 4519458