#------------------------------------------------------------------------------ #$Date: 2023-11-01 19:20:55 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287221 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519472.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_4519472 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, 0.984(Br), 1.016(Cl), 2(H2 O)' _chemical_formula_sum 'C12 H18 Br0.98 Cl1.02 N2 O2' _chemical_formula_weight 336.98 _chemical_name_common ; Paraquat Bromide Chloride 0.98:1.02 Dihydrate ; _chemical_name_systematic ; 1,1'-dimethyl-4,4'-bipyridin-1-ium bromide chloride dihydrate ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _cell_angle_alpha 107.616(1) _cell_angle_beta 100.811(1) _cell_angle_gamma 93.396(1) _cell_formula_units_Z 2 _cell_length_a 7.0732(2) _cell_length_b 9.8786(3) _cell_length_c 11.4345(3) _cell_measurement_reflns_used 6366 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.915 _cell_measurement_theta_min 3.615 _cell_volume 742.22(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 4 (2022) 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 'XT (Sheldrick, 2015)' _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 0.951 _diffrn_measured_fraction_theta_max 0.941 _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 0.0213 _diffrn_reflns_av_unetI/netI 0.0259 _diffrn_reflns_Laue_measured_fraction_full 0.951 _diffrn_reflns_Laue_measured_fraction_max 0.941 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6830 _diffrn_reflns_point_group_measured_fraction_full 0.951 _diffrn_reflns_point_group_measured_fraction_max 0.941 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.940 _diffrn_reflns_theta_min 3.614 _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 3.570 _exptl_absorpt_correction_T_max 0.1123 _exptl_absorpt_correction_T_min 0.0356 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0782 before and 0.0457 after correction. The Ratio of minimum to maximum transmission is 0.3170. 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 1.508 _exptl_crystal_description Bock _exptl_crystal_F_000 343 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.340 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 188 _refine_ls_number_reflns 2650 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.106 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0273 _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^)+(0.0204P)^2^+0.5281P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.0725 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2537 _reflns_number_total 2650 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S26_Pq-Br_0_98_Cl_1_02_2H2O_P-1.cif _cod_data_source_block jw25533 _cod_database_code 4519472 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' 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 -0.2531(13) 0.1971(9) -0.0716(7) 0.0410(5) Uani 0.492(3) 1 d . . P A 1 Br2 Br 0.2573(8) 0.8308(6) 0.5511(3) 0.0363(4) Uani 0.492(3) 1 d . . P A 1 Cl1 Cl -0.255(3) 0.204(2) -0.0788(17) 0.0410(5) Uani 0.508(3) 1 d . . P A 2 Cl2 Cl 0.2488(19) 0.8291(13) 0.5337(8) 0.0363(4) Uani 0.508(3) 1 d . . P A 2 C1 C 0.2302(3) 0.3567(2) 0.4787(2) 0.0449(5) Uani 1 1 d . . . . . H1 H 0.155446 0.370555 0.405994 0.054 Uiso 1 1 calc R U . . . N1 N 0.2560(3) 0.2237(2) 0.47968(17) 0.0404(4) Uani 1 1 d . . . . . C2 C 0.3106(3) 0.4732(2) 0.5818(2) 0.0439(5) Uani 1 1 d . . . . . H2 H 0.292130 0.566994 0.579853 0.053 Uiso 1 1 calc R U . . . N2 N 0.7048(3) 0.80836(19) 1.00326(17) 0.0393(4) Uani 1 1 d . . . . . C3 C 0.4194(3) 0.4538(2) 0.6895(2) 0.0367(5) Uani 1 1 d . . . . . C4 C 0.4360(3) 0.3139(2) 0.6884(2) 0.0400(5) Uani 1 1 d . . . . . H4 H 0.504001 0.296473 0.761384 0.048 Uiso 1 1 calc R U . . . C5 C 0.3551(3) 0.2011(2) 0.5831(2) 0.0420(5) Uani 1 1 d . . . . . H5 H 0.369131 0.106043 0.583077 0.050 Uiso 1 1 calc R U . . . C6 C 0.1832(4) 0.1002(3) 0.3647(2) 0.0499(6) Uani 1 1 d . . . . . H6A H 0.099091 0.131306 0.301888 0.075 Uiso 1 1 calc R U . . . H6B H 0.109286 0.026438 0.385016 0.075 Uiso 1 1 calc R U . . . H6C H 0.293063 0.060788 0.331048 0.075 Uiso 1 1 calc R U . . . C7 C 0.6052(3) 0.8303(2) 0.9003(2) 0.0413(5) Uani 1 1 d . . . . . H7 H 0.600507 0.925346 0.897750 0.050 Uiso 1 1 calc R U . . . C8 C 0.5095(3) 0.7174(2) 0.7981(2) 0.0404(5) Uani 1 1 d . . . . . H8 H 0.438016 0.735024 0.726185 0.048 Uiso 1 1 calc R U . . . C9 C 0.5170(3) 0.5776(2) 0.7997(2) 0.0372(5) Uani 1 1 d . . . . . C10 C 0.6253(3) 0.5585(2) 0.9077(2) 0.0388(5) Uani 1 1 d . . . . . H10 H 0.636029 0.464528 0.911677 0.047 Uiso 1 1 calc R U . . . C11 C 0.7162(3) 0.6744(2) 1.0080(2) 0.0401(5) Uani 1 1 d . . . . . H11 H 0.787754 0.660039 1.081481 0.048 Uiso 1 1 calc R U . . . C12 C 0.7963(4) 0.9310(3) 1.1150(2) 0.0494(6) Uani 1 1 d . . . . . H12A H 0.807882 1.017659 1.090773 0.074 Uiso 1 1 calc R U . . . H12B H 0.925514 0.912300 1.150471 0.074 Uiso 1 1 calc R U . . . H12C H 0.716182 0.944389 1.177923 0.074 Uiso 1 1 calc R U . . . O1 O -0.0098(3) 0.3687(3) 0.2158(2) 0.0647(5) Uani 1 1 d D . . . . H1A H -0.074(5) 0.322(4) 0.145(3) 0.104(15) Uiso 1 1 d D . . . . H1B H 0.017(5) 0.453(3) 0.221(3) 0.086(12) Uiso 1 1 d D . . . . O2 O 0.0433(3) 0.6702(2) 0.2548(2) 0.0622(5) Uani 1 1 d D . . . . H2A H 0.092(5) 0.708(4) 0.331(2) 0.088(12) Uiso 1 1 d D . . . . H2B H 0.109(5) 0.711(4) 0.220(3) 0.087(12) Uiso 1 1 d 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 0.0462(3) 0.0389(7) 0.0399(9) 0.0155(5) 0.0087(5) 0.0072(4) Br2 0.0423(5) 0.0366(2) 0.0305(11) 0.0137(7) 0.0044(8) 0.0052(3) Cl1 0.0462(3) 0.0389(7) 0.0399(9) 0.0155(5) 0.0087(5) 0.0072(4) Cl2 0.0423(5) 0.0366(2) 0.0305(11) 0.0137(7) 0.0044(8) 0.0052(3) C1 0.0478(13) 0.0450(13) 0.0394(12) 0.0140(10) 0.0030(10) 0.0056(10) N1 0.0389(10) 0.0398(10) 0.0371(10) 0.0067(8) 0.0055(8) 0.0014(8) C2 0.0482(13) 0.0389(12) 0.0416(12) 0.0122(10) 0.0033(10) 0.0057(10) N2 0.0375(10) 0.0390(10) 0.0361(10) 0.0062(8) 0.0052(8) 0.0042(8) C3 0.0350(11) 0.0382(11) 0.0363(11) 0.0105(9) 0.0086(9) 0.0044(9) C4 0.0412(12) 0.0408(12) 0.0364(11) 0.0118(9) 0.0054(9) 0.0051(9) C5 0.0429(12) 0.0385(11) 0.0423(12) 0.0114(10) 0.0066(10) 0.0053(9) C6 0.0556(15) 0.0426(13) 0.0407(13) 0.0031(10) 0.0032(11) 0.0007(11) C7 0.0437(12) 0.0373(11) 0.0417(12) 0.0123(9) 0.0067(10) 0.0070(9) C8 0.0427(12) 0.0398(11) 0.0362(11) 0.0116(9) 0.0037(9) 0.0049(9) C9 0.0365(11) 0.0396(11) 0.0351(11) 0.0105(9) 0.0093(9) 0.0054(9) C10 0.0410(12) 0.0376(11) 0.0377(11) 0.0124(9) 0.0076(9) 0.0049(9) C11 0.0398(12) 0.0430(12) 0.0383(11) 0.0143(9) 0.0075(9) 0.0073(9) C12 0.0508(14) 0.0411(12) 0.0434(13) 0.0018(10) -0.0018(11) 0.0056(11) O1 0.0655(13) 0.0757(15) 0.0551(12) 0.0315(11) 0.0025(10) 0.0020(11) O2 0.0554(12) 0.0759(14) 0.0534(12) 0.0243(11) 0.0043(10) -0.0034(10) 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 119.7 . . N1 C1 C2 120.7(2) . . C2 C1 H1 119.7 . . C1 N1 C5 120.7(2) . . C1 N1 C6 120.2(2) . . C5 N1 C6 119.0(2) . . C1 C2 H2 120.0 . . C1 C2 C3 120.1(2) . . C3 C2 H2 120.0 . . C7 N2 C11 120.48(19) . . C7 N2 C12 120.26(19) . . C11 N2 C12 119.2(2) . . C2 C3 C9 121.3(2) . . C4 C3 C2 117.4(2) . . C4 C3 C9 121.3(2) . . C3 C4 H4 119.8 . . C5 C4 C3 120.5(2) . . C5 C4 H4 119.8 . . N1 C5 C4 120.6(2) . . 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 119.5 . . N2 C7 C8 121.0(2) . . C8 C7 H7 119.5 . . C7 C8 H8 119.9 . . C7 C8 C9 120.2(2) . . C9 C8 H8 119.9 . . C8 C9 C3 121.3(2) . . C8 C9 C10 117.2(2) . . C10 C9 C3 121.4(2) . . C9 C10 H10 119.7 . . C11 C10 C9 120.5(2) . . C11 C10 H10 119.7 . . N2 C11 C10 120.5(2) . . 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 . . H1A O1 H1B 111(4) . . H2A O2 H2B 104(4) . . 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(3) . C1 C2 1.374(3) . N1 C5 1.344(3) . N1 C6 1.477(3) . C2 H2 0.9500 . C2 C3 1.396(3) . N2 C7 1.338(3) . N2 C11 1.348(3) . N2 C12 1.476(3) . C3 C4 1.391(3) . C3 C9 1.484(3) . C4 H4 0.9500 . C4 C5 1.369(3) . C5 H5 0.9500 . C6 H6A 0.9800 . C6 H6B 0.9800 . C6 H6C 0.9800 . C7 H7 0.9500 . C7 C8 1.376(3) . C8 H8 0.9500 . C8 C9 1.391(3) . C9 C10 1.396(3) . C10 H10 0.9500 . C10 C11 1.372(3) . C11 H11 0.9500 . C12 H12A 0.9800 . C12 H12B 0.9800 . C12 H12C 0.9800 . O1 H1A 0.83(2) . O1 H1B 0.82(2) . O2 H2A 0.84(2) . O2 H2B 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 O1 0.95 2.26 3.204(3) 170.7 . yes C2 H2 Br2 0.95 2.74 3.689(6) 173.6 . yes C2 H2 Cl2 0.95 2.82 3.758(12) 170.5 . yes C4 H4 Br1 0.95 2.77 3.695(9) 164.9 1_656 yes C4 H4 Cl1 0.95 2.67 3.59(2) 164.3 1_656 yes C5 H5 Br2 0.95 2.68 3.576(6) 157.3 1_545 yes C5 H5 Cl2 0.95 2.67 3.556(13) 155.2 1_545 yes C7 H7 Br1 0.95 2.71 3.602(9) 155.9 1_666 yes C7 H7 Cl1 0.95 2.79 3.68(2) 157.0 1_666 yes C8 H8 Br2 0.95 2.62 3.560(5) 170.0 . yes C8 H8 Cl2 0.95 2.79 3.731(10) 171.5 . yes C10 H10 Br1 0.95 2.85 3.787(9) 168.8 1_656 yes C10 H10 Cl1 0.95 2.76 3.70(2) 168.3 1_656 yes C11 H11 O2 0.95 2.39 3.309(3) 162.3 1_656 yes C12 H12A Br1 0.98 2.93 3.848(9) 157.4 1_666 yes C12 H12B Br1 0.98 2.80 3.604(10) 139.8 2_666 yes C12 H12B Cl1 0.98 2.81 3.62(2) 141.5 2_666 yes O1 H1A Br1 0.83(2) 2.46(3) 3.285(8) 175(4) . yes O1 H1A Cl1 0.83(2) 2.52(3) 3.340(18) 173(4) . yes O1 H1B O2 0.82(2) 2.06(2) 2.865(3) 169(4) . yes O2 H2A Br2 0.84(2) 2.46(2) 3.290(4) 175(4) . yes O2 H2A Cl2 0.84(2) 2.29(3) 3.116(10) 173(4) . yes O2 H2B Br1 0.83(2) 2.49(3) 3.303(9) 167(3) 2_565 yes O2 H2B Cl1 0.83(2) 2.39(3) 3.20(2) 168(3) 2_565 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 -1.7(3) . . . . C1 C2 C3 C4 -2.1(3) . . . . C1 C2 C3 C9 176.6(2) . . . . N1 C1 C2 C3 -0.5(4) . . . . C2 C1 N1 C5 2.5(3) . . . . C2 C1 N1 C6 -174.7(2) . . . . C2 C3 C4 C5 2.8(3) . . . . C2 C3 C9 C8 -2.4(3) . . . . C2 C3 C9 C10 179.7(2) . . . . N2 C7 C8 C9 -0.8(3) . . . . C3 C4 C5 N1 -1.0(3) . . . . C3 C9 C10 C11 179.3(2) . . . . C4 C3 C9 C8 176.4(2) . . . . C4 C3 C9 C10 -1.6(3) . . . . C6 N1 C5 C4 175.5(2) . . . . C7 N2 C11 C10 -0.3(3) . . . . C7 C8 C9 C3 -178.4(2) . . . . C7 C8 C9 C10 -0.4(3) . . . . C8 C9 C10 C11 1.3(3) . . . . C9 C3 C4 C5 -175.9(2) . . . . C9 C10 C11 N2 -1.0(3) . . . . C11 N2 C7 C8 1.2(3) . . . . C12 N2 C7 C8 -176.1(2) . . . . C12 N2 C11 C10 177.1(2) . . . . _cod_database_fobs_code 4519472