#------------------------------------------------------------------------------ #$Date: 2023-11-01 18:56:55 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287208 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519459.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_4519459 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, 1.194(I1), 0.806(Br)' _chemical_formula_sum 'C12 H14 Br0.81 I1.19 N2' _chemical_formula_weight 402.22 _chemical_name_common 'Paraquat Iodie Bromide 1.19:0.81' _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 direct _cell_angle_alpha 90 _cell_angle_beta 95.874(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.0376(4) _cell_length_b 8.1443(5) _cell_length_c 13.9403(8) _cell_measurement_reflns_used 5268 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.959 _cell_measurement_theta_min 4.725 _cell_volume 681.87(7) _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 0.990 _diffrn_measured_fraction_theta_max 0.989 _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 0.0452 _diffrn_reflns_av_unetI/netI 0.0371 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.989 _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 5813 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.964 _diffrn_reflns_theta_min 5.480 _diffrn_source 'Metal Jet' _diffrn_source_current 2.86 _diffrn_source_power 0.19945639999999998 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.74 _exptl_absorpt_coefficient_mu 16.755 _exptl_absorpt_correction_T_max 0.1123 _exptl_absorpt_correction_T_min 0.0196 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1601 before and 0.0834 after correction. The Ratio of minimum to maximum transmission is 0.1745. 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 1.959 _exptl_crystal_description Fragment _exptl_crystal_F_000 383 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _refine_diff_density_max 1.198 _refine_diff_density_min -0.738 _refine_diff_density_rms 0.137 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 78 _refine_ls_number_reflns 1292 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0388 _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^)+(0.0732P)^2^+0.5065P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1099 _refine_ls_wR_factor_ref 0.1110 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1228 _reflns_number_total 1292 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S13_Pq-Br_0_81_I_1_19_P21_c.cif _cod_data_source_block jw25371 _cod_database_code 4519459 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 0.819(2) 0.5833(17) 0.3301(10) 0.0465(4) Uani 0.403(15) 1 d . . P A 1 I1 I 0.8328(9) 0.5769(7) 0.3224(4) 0.0465(4) Uani 0.597(15) 1 d . . P A 2 C1 C 0.6376(8) 0.1729(6) 0.3658(3) 0.0533(11) Uani 1 1 d . . . . . H1 H 0.590416 0.194360 0.299911 0.064 Uiso 1 1 calc R U . . . N1 N 0.5243(6) 0.2363(4) 0.4348(3) 0.0481(9) Uani 1 1 d . . . . . C2 C 0.8232(9) 0.0760(5) 0.3904(4) 0.0509(12) Uani 1 1 d . . . . . H2 H 0.899513 0.027929 0.341112 0.061 Uiso 1 1 calc R U . . . C3 C 0.8984(7) 0.0489(5) 0.4860(3) 0.0454(10) Uani 1 1 d . . . . . C4 C 0.7760(8) 0.1188(6) 0.5561(4) 0.0513(11) Uani 1 1 d . . . . . H4 H 0.821978 0.102675 0.622671 0.062 Uiso 1 1 calc R U . . . C5 C 0.5902(8) 0.2104(5) 0.5282(3) 0.0504(10) Uani 1 1 d . . . . . H5 H 0.506725 0.256160 0.575838 0.061 Uiso 1 1 calc R U . . . C6 C 0.3270(8) 0.3405(6) 0.4053(4) 0.0554(11) Uani 1 1 d . . . . . H6A H 0.376025 0.445082 0.379778 0.083 Uiso 1 1 calc R U . . . H6B H 0.245248 0.361369 0.461231 0.083 Uiso 1 1 calc R U . . . H6C H 0.229657 0.283805 0.355277 0.083 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 0.0437(8) 0.0450(5) 0.0524(9) -0.0017(5) 0.0126(5) 0.0022(4) I1 0.0437(8) 0.0450(5) 0.0524(9) -0.0017(5) 0.0126(5) 0.0022(4) C1 0.050(3) 0.054(2) 0.056(2) 0.002(2) 0.0116(19) -0.001(2) N1 0.0427(19) 0.0382(18) 0.064(2) 0.0010(15) 0.0065(16) -0.0043(13) C2 0.044(3) 0.056(3) 0.053(3) -0.0020(17) 0.0099(19) -0.0012(16) C3 0.041(2) 0.0352(18) 0.061(2) -0.0022(17) 0.0079(18) -0.0078(16) C4 0.052(3) 0.044(2) 0.059(3) -0.0030(19) 0.009(2) 0.0003(19) C5 0.047(2) 0.042(2) 0.063(3) -0.0050(18) 0.0097(18) 0.0011(18) C6 0.047(2) 0.044(2) 0.075(3) 0.001(2) 0.007(2) 0.0016(18) 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 119.9 . . N1 C1 C2 120.1(4) . . C2 C1 H1 119.9 . . C1 N1 C6 118.4(4) . . C5 N1 C1 121.0(4) . . C5 N1 C6 120.6(4) . . C1 C2 H2 119.7 . . C3 C2 C1 120.5(4) . . C3 C2 H2 119.7 . . C2 C3 C3 121.4(5) . 3_756 C2 C3 C4 117.5(4) . . C4 C3 C3 121.1(5) . 3_756 C3 C4 H4 120.1 . . C5 C4 C3 119.8(5) . . C5 C4 H4 120.1 . . N1 C5 C4 121.0(4) . . 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 C1 H1 0.9500 . C1 N1 1.339(6) . C1 C2 1.385(7) . N1 C5 1.339(6) . N1 C6 1.486(6) . C2 H2 0.9500 . C2 C3 1.382(7) . C3 C3 1.481(9) 3_756 C3 C4 1.404(7) . C4 H4 0.9500 . C4 C5 1.370(6) . 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 0.3(6) . . . . C1 C2 C3 C3 -177.6(5) . . . 3_756 C1 C2 C3 C4 1.8(6) . . . . N1 C1 C2 C3 -2.4(7) . . . . C2 C1 N1 C5 1.3(6) . . . . C2 C1 N1 C6 179.6(4) . . . . C2 C3 C4 C5 -0.2(6) . . . . C3 C3 C4 C5 179.2(5) 3_756 . . . C3 C4 C5 N1 -0.9(7) . . . . C6 N1 C5 C4 -177.9(4) . . . . _cod_database_fobs_code 4519459