#------------------------------------------------------------------------------ #$Date: 2023-11-01 19:05:20 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287213 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519464.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_4519464 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, 0.411(Br), 1.589(Cl), 3(H2 O)' _chemical_formula_sum 'C12 H20 Br0.41 Cl1.59 N2 O3' _chemical_formula_weight 329.54 _chemical_name_common ; Paraquat Bromide Chloride 0.41:1.59 trihydrate ; _chemical_name_systematic ; 1,1'-dimethyl-4,4'-bipyridin-1-ium chloride bromide trihydrate ; _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 mixed _atom_sites_solution_primary dual _cell_angle_alpha 90 _cell_angle_beta 109.2330(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.1298(3) _cell_length_b 16.0379(5) _cell_length_c 11.3215(3) _cell_measurement_reflns_used 9968 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.898 _cell_measurement_theta_min 4.325 _cell_volume 1565.20(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 0.984 _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 0.0222 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 14683 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.884 _diffrn_reflns_theta_min 4.324 _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 2.898 _exptl_absorpt_correction_T_max 0.2006 _exptl_absorpt_correction_T_min 0.1132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1088 before and 0.0451 after correction. The Ratio of minimum to maximum transmission is 0.5643. 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 1.398 _exptl_crystal_description Fragment _exptl_crystal_F_000 686 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.204 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 207 _refine_ls_number_reflns 2927 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.940 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0234 _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^)+(0.0460P)^2^+0.3795P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.0686 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2749 _reflns_number_total 2927 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S19_Pq-Br_0_41_Cl_1_59_3H2O.cif _cod_data_source_block jw25292 _cod_database_code 4519464 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 Cl1 Cl 1.000000 0.500000 0.500000 0.03379(16) Uani 0.846(2) 2 d S . P A 1 Cl2 Cl 0.500000 0.000000 0.500000 0.03349(12) Uani 0.547(3) 2 d S . P B 1 Cl3 Cl 0.0362(7) 0.1978(4) 0.4939(6) 0.0334(2) Uani 0.893(2) 1 d . . P C 1 Br1 Br 1.000000 0.500000 0.500000 0.03379(16) Uani 0.154(2) 2 d S . P A 2 Br2 Br 0.500000 0.000000 0.500000 0.03349(12) Uani 0.453(3) 2 d S . P B 2 Br3 Br 0.033(3) 0.1958(14) 0.496(2) 0.0334(2) Uani 0.107(2) 1 d . . P C 2 C1 C 0.60969(15) 0.54333(8) 0.32773(12) 0.0369(3) Uani 1 1 d . . . . . H1 H 0.709913 0.521503 0.370527 0.044 Uiso 1 1 calc R U . . . H2A H 0.616(3) 0.3165(11) 0.5080(18) 0.071(6) Uiso 1 1 d . . . . . N1 N 0.59588(12) 0.61811(6) 0.27144(10) 0.0333(3) Uani 1 1 d . . . . . C2 C 0.48060(16) 0.49818(7) 0.32402(13) 0.0361(3) Uani 1 1 d . . . . . H2 H 0.491853 0.445580 0.364626 0.043 Uiso 1 1 calc R U . . . N2 N -0.07160(12) 0.38824(6) 0.22866(9) 0.0319(3) Uani 1 1 d . . . . . O2 O 0.51953(14) 0.30920(7) 0.47372(11) 0.0481(3) Uani 1 1 d . . . . . H2B H 0.491(2) 0.2717(13) 0.5131(16) 0.060(6) Uiso 1 1 d . . . . . C3 C 0.33284(14) 0.52936(7) 0.26077(11) 0.0307(3) Uani 1 1 d . . . . . C4 C 0.32320(14) 0.60820(7) 0.20673(12) 0.0335(3) Uani 1 1 d . . . . . H4 H 0.224521 0.632422 0.165743 0.040 Uiso 1 1 calc R U . . . C5 C 0.45544(15) 0.65090(7) 0.21249(12) 0.0346(3) Uani 1 1 d . . . . . H5 H 0.447625 0.704233 0.174375 0.042 Uiso 1 1 calc R U . . . C6 C 0.73625(15) 0.66223(9) 0.26796(14) 0.0421(3) Uani 1 1 d . . . . . H6A H 0.826618 0.641863 0.335851 0.063 Uiso 1 1 calc R U . . . H6B H 0.724003 0.722221 0.278296 0.063 Uiso 1 1 calc R U . . . H6C H 0.751339 0.651918 0.187430 0.063 Uiso 1 1 calc R U . . . C7 C 0.06733(15) 0.35956(8) 0.29965(12) 0.0343(3) Uani 1 1 d . . . . . H7 H 0.074180 0.308027 0.342518 0.041 Uiso 1 1 calc R U . . . C8 C 0.19991(14) 0.40394(8) 0.31105(12) 0.0336(3) Uani 1 1 d . . . . . H8 H 0.297879 0.382763 0.361100 0.040 Uiso 1 1 calc R U . . . C9 C 0.19126(14) 0.47974(8) 0.24958(11) 0.0301(3) Uani 1 1 d . . . . . C10 C 0.04473(16) 0.50734(7) 0.17562(13) 0.0346(3) Uani 1 1 d . . . . . H10 H 0.034405 0.558540 0.131424 0.042 Uiso 1 1 calc R U . . . C11 C -0.08435(14) 0.46064(8) 0.16664(12) 0.0347(3) Uani 1 1 d . . . . . H11 H -0.183714 0.479729 0.116044 0.042 Uiso 1 1 calc R U . . . C12 C -0.21226(16) 0.33986(8) 0.22011(14) 0.0411(3) Uani 1 1 d . . . . . H12A H -0.195785 0.281171 0.203912 0.062 Uiso 1 1 calc R U . . . H12B H -0.300395 0.361783 0.151698 0.062 Uiso 1 1 calc R U . . . H12C H -0.233985 0.344507 0.299051 0.062 Uiso 1 1 calc R U . . . O3 O 0.40313(14) 0.18012(8) 0.58820(12) 0.0566(3) Uani 1 1 d . . . . . H3A H 0.417(2) 0.1312(13) 0.5596(19) 0.075(6) Uiso 1 1 d . . . . . H3B H 0.306(3) 0.1829(12) 0.5623(19) 0.071(6) Uiso 1 1 d . . . . . O1 O 0.83885(14) 0.33914(8) 0.56941(13) 0.0568(3) Uani 1 1 d . . . . . H1A H 0.874(2) 0.3851(13) 0.5486(18) 0.072(6) Uiso 1 1 d . . . . . H1B H 0.887(3) 0.3013(13) 0.5487(19) 0.075(7) 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 Cl1 0.0297(2) 0.0363(2) 0.0333(2) -0.00243(12) 0.00754(16) 0.00368(12) Cl2 0.03002(17) 0.03669(19) 0.03179(18) 0.00261(9) 0.00750(12) -0.00216(9) Cl3 0.0348(3) 0.0282(3) 0.0336(3) 0.0000(2) 0.0064(2) -0.0047(2) Br1 0.0297(2) 0.0363(2) 0.0333(2) -0.00243(12) 0.00754(16) 0.00368(12) Br2 0.03002(17) 0.03669(19) 0.03179(18) 0.00261(9) 0.00750(12) -0.00216(9) Br3 0.0348(3) 0.0282(3) 0.0336(3) 0.0000(2) 0.0064(2) -0.0047(2) C1 0.0304(6) 0.0388(7) 0.0371(7) 0.0008(5) 0.0051(5) 0.0025(5) N1 0.0311(5) 0.0346(6) 0.0327(6) -0.0053(4) 0.0087(4) -0.0035(4) C2 0.0335(7) 0.0351(7) 0.0371(8) 0.0046(5) 0.0083(6) 0.0022(5) N2 0.0317(5) 0.0308(5) 0.0330(6) -0.0025(4) 0.0106(4) -0.0004(4) O2 0.0436(6) 0.0421(6) 0.0490(6) 0.0044(5) 0.0022(5) 0.0050(5) C3 0.0320(6) 0.0309(6) 0.0286(6) -0.0015(5) 0.0093(5) 0.0026(5) C4 0.0302(6) 0.0329(6) 0.0352(7) 0.0009(5) 0.0080(5) 0.0030(5) C5 0.0365(7) 0.0303(6) 0.0358(7) -0.0008(5) 0.0101(5) 0.0008(5) C6 0.0332(7) 0.0402(7) 0.0503(8) -0.0044(6) 0.0104(6) -0.0083(5) C7 0.0367(7) 0.0304(6) 0.0356(7) 0.0022(5) 0.0113(5) 0.0025(5) C8 0.0314(6) 0.0340(6) 0.0339(7) 0.0027(5) 0.0087(5) 0.0045(5) C9 0.0308(6) 0.0305(6) 0.0293(6) -0.0016(5) 0.0101(5) 0.0018(5) C10 0.0330(7) 0.0324(6) 0.0364(7) 0.0049(5) 0.0087(6) 0.0028(5) C11 0.0312(6) 0.0336(6) 0.0358(7) 0.0004(5) 0.0064(5) 0.0019(5) C12 0.0353(7) 0.0365(7) 0.0500(8) -0.0014(6) 0.0122(6) -0.0074(5) O3 0.0396(6) 0.0534(7) 0.0737(8) -0.0058(6) 0.0144(6) -0.0005(5) O1 0.0476(6) 0.0512(7) 0.0787(8) -0.0028(6) 0.0304(6) -0.0024(5) 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' O O 0.0389 0.0241 '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 120.72(11) . . C2 C1 H1 119.6 . . C1 N1 C6 119.59(11) . . C5 N1 C1 120.68(11) . . C5 N1 C6 119.63(11) . . C1 C2 H2 119.9 . . C1 C2 C3 120.15(11) . . C3 C2 H2 119.9 . . C7 N2 C11 120.85(11) . . C7 N2 C12 119.35(11) . . C11 N2 C12 119.80(10) . . H2A O2 H2B 108.6(17) . . C2 C3 C9 121.21(12) . . C4 C3 C2 117.43(11) . . C4 C3 C9 121.35(11) . . C3 C4 H4 119.8 . . C5 C4 C3 120.32(11) . . C5 C4 H4 119.8 . . N1 C5 C4 120.65(11) . . N1 C5 H5 119.7 . . C4 C5 H5 119.7 . . 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 . . N2 C7 H7 119.7 . . N2 C7 C8 120.63(11) . . C8 C7 H7 119.7 . . C7 C8 H8 119.9 . . C7 C8 C9 120.22(11) . . C9 C8 H8 119.9 . . C8 C9 C3 121.39(12) . . C8 C9 C10 117.56(12) . . C10 C9 C3 121.04(12) . . C9 C10 H10 119.9 . . C11 C10 C9 120.11(12) . . C11 C10 H10 119.9 . . N2 C11 C10 120.62(11) . . N2 C11 H11 119.7 . . C10 C11 H11 119.7 . . N2 C12 H12A 109.5 . . N2 C12 H12B 109.5 . . N2 C12 H12C 109.5 . . H12A C12 H12B 109.5 . . H12A C12 H12C 109.5 . . H12B C12 H12C 109.5 . . H3A O3 H3B 100.7(18) . . H1A O1 H1B 105.5(19) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 H1 0.9500 . C1 N1 1.3444(16) . C1 C2 1.3720(18) . N1 C5 1.3425(16) . N1 C6 1.4758(16) . C2 H2 0.9500 . C2 C3 1.3951(18) . N2 C7 1.3397(16) . N2 C11 1.3420(16) . N2 C12 1.4761(15) . O2 H2A 0.85(2) . O2 H2B 0.84(2) . C3 C4 1.3947(17) . C3 C9 1.4874(18) . C4 H4 0.9500 . C4 C5 1.3708(18) . C5 H5 0.9500 . C6 H6A 0.9800 . C6 H6B 0.9800 . C6 H6C 0.9800 . C7 H7 0.9500 . C7 C8 1.3732(18) . C8 H8 0.9500 . C8 C9 1.3901(17) . C9 C10 1.3960(18) . C10 H10 0.9500 . C10 C11 1.3715(18) . C11 H11 0.9500 . C12 H12A 0.9800 . C12 H12B 0.9800 . C12 H12C 0.9800 . O3 H3A 0.87(2) . O3 H3B 0.84(2) . O1 H1A 0.87(2) . O1 H1B 0.83(2) . 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 C1 H1 Cl1 0.95 2.59 3.5223(12) 166.0 . yes O2 H2A O1 0.85(2) 1.95(2) 2.7969(17) 173.6(19) . yes C2 H2 O2 0.95 2.48 3.4334(17) 179.0 . yes O2 H2B O3 0.84(2) 1.99(2) 2.8289(18) 173.5(17) . yes C4 H4 Cl3 0.95 2.68 3.617(6) 167.7 2 yes C5 H5 O2 0.95 2.46 3.3555(17) 156.5 2_655 yes C7 H7 Cl3 0.95 2.56 3.474(6) 160.2 . yes C8 H8 O2 0.95 2.33 3.2672(16) 170.5 . yes C10 H10 Cl3 0.95 2.61 3.553(6) 171.8 2 yes C11 H11 Cl2 0.95 2.77 3.6935(12) 164.4 2 yes O3 H3A Cl2 0.87(2) 2.41(2) 3.2720(13) 170.6(18) . yes O3 H3B Cl3 0.84(2) 2.34(2) 3.176(6) 177.0(18) . yes O1 H1A Cl1 0.87(2) 2.33(2) 3.1937(13) 172.3(18) . yes O1 H1B Cl3 0.83(2) 2.35(2) 3.183(7) 177(2) 1_655 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 -1.06(19) . . . . C1 C2 C3 C4 -2.25(19) . . . . C1 C2 C3 C9 176.72(12) . . . . N1 C1 C2 C3 0.4(2) . . . . C2 C1 N1 C5 1.29(19) . . . . C2 C1 N1 C6 -175.02(13) . . . . C2 C3 C4 C5 2.48(18) . . . . C2 C3 C9 C8 5.9(2) . . . . C2 C3 C9 C10 -173.38(11) . . . . N2 C7 C8 C9 0.52(19) . . . . C3 C4 C5 N1 -0.88(19) . . . . C3 C9 C10 C11 -179.97(12) . . . . C4 C3 C9 C8 -175.18(10) . . . . C4 C3 C9 C10 5.54(19) . . . . C6 N1 C5 C4 175.25(12) . . . . C7 N2 C11 C10 -0.65(19) . . . . C7 C8 C9 C3 179.67(12) . . . . C7 C8 C9 C10 -1.03(18) . . . . C8 C9 C10 C11 0.73(19) . . . . C9 C3 C4 C5 -176.48(12) . . . . C9 C10 C11 N2 0.1(2) . . . . C11 N2 C7 C8 0.35(18) . . . . C12 N2 C7 C8 -178.89(12) . . . . C12 N2 C11 C10 178.59(12) . . . . _cod_database_fobs_code 4519464