#------------------------------------------------------------------------------ #$Date: 2023-11-01 18:43:16 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287200 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519451.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_4519451 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 '2(Cl), 3(H2 O), C12 H14 N2' _chemical_formula_sum 'C12 H20 Cl2 N2 O3' _chemical_formula_weight 311.20 _chemical_name_common 'Paraquat Dichloride Trihydrate' _chemical_name_systematic ; 1,1'-dimethyl-4,4'-bipyridin-1-ium bis(chloride) 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 difmap _atom_sites_solution_primary dual _cell_angle_alpha 90 _cell_angle_beta 108.852(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0643(2) _cell_length_b 16.0149(3) _cell_length_c 11.2228(2) _cell_measurement_reflns_used 9993 _cell_measurement_temperature 150 _cell_measurement_theta_max 60.648 _cell_measurement_theta_min 4.347 _cell_volume 1541.75(5) _computing_cell_refinement ; SAINT (2013) 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 (2013) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (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 0.984 _diffrn_measured_fraction_theta_max 0.987 _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 0.0311 _diffrn_reflns_av_unetI/netI 0.0228 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 25232 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.618 _diffrn_reflns_theta_min 4.346 _diffrn_source 'Metal Jet' _diffrn_source_current 2.86 _diffrn_source_power 0.199914 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.9 _exptl_absorpt_coefficient_mu 2.548 _exptl_absorpt_correction_T_max 0.4146 _exptl_absorpt_correction_T_min 0.3168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1188 before and 0.0487 after correction. The Ratio of minimum to maximum transmission is 0.7641. 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 1.341 _exptl_crystal_description Block _exptl_crystal_F_000 656 _exptl_crystal_recrystallization_method 'crystallzed from DMSO/H2O on a microscope slide' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.369 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.042 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 3503 _refine_ls_number_restraints 43 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_gt 0.0259 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.2832P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.0751 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3417 _reflns_number_total 3503 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S05_Pq-Cl2_3H2O_P21_c.cif _cod_data_source_block jw22641 _cod_database_code 4519451 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 0.02624(10) Uani 1 2 d S . P . . Cl2 Cl 1.03369(3) 0.19753(2) 0.49330(2) 0.02624(9) Uani 1 1 d . . . . . Cl3 Cl 0.500000 0.000000 0.500000 0.02787(10) Uani 1 2 d S . P . . O1 O 0.40044(10) 0.17607(6) 0.58491(10) 0.0446(2) Uani 1 1 d . . . . . H1A H 0.306(2) 0.1787(11) 0.5659(17) 0.065(5) Uiso 1 1 d . . . . . H1B H 0.418(2) 0.1300(12) 0.5590(17) 0.064(5) Uiso 1 1 d . . . . . O2 O 0.51648(11) 0.30912(5) 0.47485(9) 0.03797(19) Uani 1 1 d . . . . . H2A H 0.611(2) 0.3178(11) 0.5075(18) 0.068(5) Uiso 1 1 d . . . . . H2B H 0.4881(19) 0.2742(11) 0.5127(14) 0.049(4) Uiso 1 1 d . . . . . O3 O 0.83725(11) 0.33975(6) 0.56775(10) 0.0450(2) Uani 1 1 d . . . . . H3A H 0.869(2) 0.3822(11) 0.5507(16) 0.055(5) Uiso 1 1 d . . . . . H3B H 0.884(3) 0.3020(12) 0.5517(19) 0.078(6) Uiso 1 1 d . . . . . N1 N -0.07686(9) 0.38835(5) 0.22661(7) 0.02222(16) Uani 1 1 d . . . . . N2 N 0.59750(9) 0.61725(5) 0.27135(7) 0.02363(17) Uani 1 1 d . . . . . C1 C -0.08906(11) 0.46104(6) 0.16443(9) 0.02477(19) Uani 1 1 d D . . . . H1 H -0.1877(9) 0.4772(8) 0.1147(11) 0.035(3) Uiso 1 1 d D . . . . C2 C 0.04180(11) 0.50773(6) 0.17360(9) 0.02455(19) Uani 1 1 d D . . . . H2 H 0.0275(15) 0.5572(6) 0.1284(11) 0.035(3) Uiso 1 1 d D . . . . C3 C 0.18874(10) 0.47938(5) 0.24762(8) 0.02065(18) Uani 1 1 d . . . . . C4 C 0.19682(11) 0.40328(6) 0.30923(9) 0.02361(18) Uani 1 1 d D . . . . H4 H 0.2896(10) 0.3801(7) 0.3595(10) 0.030(3) Uiso 1 1 d D . . . . C5 C 0.06236(11) 0.35911(6) 0.29770(9) 0.02469(19) Uani 1 1 d D . . . . H5 H 0.0647(15) 0.3088(5) 0.3393(10) 0.028(3) Uiso 1 1 d D . . . . C6 C -0.21886(12) 0.34002(7) 0.21773(11) 0.0316(2) Uani 1 1 d D . . . . H6A H -0.198(2) 0.2861(6) 0.2073(17) 0.069(5) Uiso 1 1 d D . . . . H6B H -0.235(2) 0.3434(10) 0.2927(12) 0.061(5) Uiso 1 1 d D . . . . H6C H -0.3001(17) 0.3630(10) 0.1580(14) 0.070(5) Uiso 1 1 d D . . . . C7 C 0.45691(11) 0.65036(6) 0.21132(9) 0.02511(19) Uani 1 1 d D . . . . H7 H 0.4542(16) 0.7024(5) 0.1744(11) 0.032(3) Uiso 1 1 d D . . . . C8 C 0.32270(11) 0.60763(6) 0.20479(9) 0.02406(19) Uani 1 1 d D . . . . H8 H 0.2287(10) 0.6330(7) 0.1613(11) 0.032(3) Uiso 1 1 d D . . . . C9 C 0.33160(10) 0.52867(5) 0.25903(8) 0.02076(18) Uani 1 1 d . . . . . C10 C 0.47945(12) 0.49701(6) 0.32304(10) 0.0263(2) Uani 1 1 d D . . . . H10 H 0.4939(15) 0.4453(5) 0.3624(11) 0.034(3) Uiso 1 1 d D . . . . C11 C 0.61042(11) 0.54239(6) 0.32778(9) 0.0270(2) Uani 1 1 d D . . . . H11 H 0.7110(9) 0.5243(8) 0.3684(12) 0.042(4) Uiso 1 1 d D . . . . C12 C 0.73970(12) 0.66193(7) 0.26997(11) 0.0322(2) Uani 1 1 d D . . . . H12A H 0.732(2) 0.7167(6) 0.2840(17) 0.077(6) Uiso 1 1 d D . . . . H12B H 0.749(2) 0.6562(10) 0.1929(11) 0.061(5) Uiso 1 1 d D . . . . H12C H 0.8233(16) 0.6417(11) 0.3302(15) 0.079(6) 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 Cl1 0.02240(16) 0.02961(18) 0.02543(16) -0.00208(10) 0.00596(12) 0.00354(11) Cl2 0.02722(13) 0.02227(13) 0.02649(13) -0.00017(7) 0.00489(9) -0.00426(7) Cl3 0.02426(16) 0.03267(18) 0.02574(17) 0.00219(11) 0.00680(12) -0.00289(11) O1 0.0277(4) 0.0404(5) 0.0635(6) -0.0048(4) 0.0115(4) 0.0003(3) O2 0.0334(4) 0.0332(4) 0.0392(4) 0.0048(3) 0.0005(3) 0.0051(3) O3 0.0367(5) 0.0370(5) 0.0687(6) -0.0023(4) 0.0271(4) -0.0023(4) N1 0.0213(4) 0.0218(4) 0.0238(4) -0.0024(3) 0.0077(3) -0.0008(3) N2 0.0205(4) 0.0255(4) 0.0240(4) -0.0050(3) 0.0059(3) -0.0037(3) C1 0.0202(4) 0.0251(4) 0.0267(4) 0.0009(3) 0.0044(3) 0.0021(3) C2 0.0217(4) 0.0231(4) 0.0266(5) 0.0043(3) 0.0048(4) 0.0024(3) C3 0.0200(4) 0.0222(4) 0.0199(4) -0.0006(3) 0.0066(3) 0.0017(3) C4 0.0216(4) 0.0238(4) 0.0245(4) 0.0036(3) 0.0062(3) 0.0040(3) C5 0.0257(4) 0.0223(4) 0.0264(4) 0.0027(3) 0.0090(3) 0.0020(3) C6 0.0246(5) 0.0287(5) 0.0406(6) -0.0002(4) 0.0093(4) -0.0059(4) C7 0.0253(4) 0.0221(4) 0.0273(4) 0.0001(3) 0.0076(4) 0.0004(3) C8 0.0206(4) 0.0236(4) 0.0269(4) 0.0014(3) 0.0063(3) 0.0025(3) C9 0.0199(4) 0.0224(4) 0.0196(4) -0.0004(3) 0.0058(3) 0.0018(3) C10 0.0218(4) 0.0260(5) 0.0286(5) 0.0045(3) 0.0047(4) 0.0021(3) C11 0.0199(4) 0.0295(5) 0.0281(4) 0.0013(3) 0.0028(3) 0.0021(3) C12 0.0233(5) 0.0321(5) 0.0397(5) -0.0030(4) 0.0081(4) -0.0081(4) 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' 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 H1A O1 H1B 105.0(18) . . H2A O2 H2B 110.4(16) . . H3A O3 H3B 109.5(19) . . C1 N1 C6 119.69(8) . . C5 N1 C1 121.03(8) . . C5 N1 C6 119.28(8) . . C7 N2 C12 119.52(8) . . C11 N2 C7 120.85(8) . . C11 N2 C12 119.56(8) . . N1 C1 H1 117.2(8) . . N1 C1 C2 120.48(8) . . C2 C1 H1 122.3(8) . . C1 C2 H2 117.3(8) . . C1 C2 C3 120.00(8) . . C3 C2 H2 122.7(8) . . C2 C3 C9 120.99(8) . . C4 C3 C2 117.82(8) . . C4 C3 C9 121.19(8) . . C3 C4 H4 123.1(8) . . C5 C4 C3 119.99(8) . . C5 C4 H4 116.9(8) . . N1 C5 C4 120.68(8) . . N1 C5 H5 117.8(8) . . C4 C5 H5 121.5(8) . . N1 C6 H6A 107.4(12) . . N1 C6 H6B 107.8(12) . . N1 C6 H6C 108.8(12) . . H6A C6 H6B 106.4(15) . . H6A C6 H6C 116.8(16) . . H6B C6 H6C 109.2(16) . . N2 C7 H7 117.5(8) . . N2 C7 C8 120.62(8) . . C8 C7 H7 121.8(8) . . C7 C8 H8 117.2(8) . . C7 C8 C9 120.13(8) . . C9 C8 H8 122.7(8) . . C8 C9 C3 121.21(8) . . C8 C9 C10 117.70(8) . . C10 C9 C3 121.09(8) . . C9 C10 H10 122.2(8) . . C11 C10 C9 120.02(8) . . C11 C10 H10 117.7(8) . . N2 C11 C10 120.64(8) . . N2 C11 H11 115.7(9) . . C10 C11 H11 123.6(9) . . N2 C12 H12A 110.6(13) . . N2 C12 H12B 108.1(11) . . N2 C12 H12C 110.2(13) . . H12A C12 H12B 107.7(16) . . H12A C12 H12C 108.4(16) . . H12B C12 H12C 111.7(17) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 H1A 0.81(2) . O1 H1B 0.83(2) . O2 H2A 0.83(2) . O2 H2B 0.794(17) . O3 H3A 0.787(19) . O3 H3B 0.79(2) . N1 C1 1.3433(12) . N1 C5 1.3408(12) . N1 C6 1.4775(12) . N2 C7 1.3432(12) . N2 C11 1.3432(13) . N2 C12 1.4787(12) . C1 H1 0.925(6) . C1 C2 1.3777(13) . C2 H2 0.927(6) . C2 C3 1.3983(12) . C3 C4 1.3915(12) . C3 C9 1.4863(13) . C4 H4 0.926(6) . C4 C5 1.3786(13) . C5 H5 0.928(6) . C6 H6A 0.900(9) . C6 H6B 0.901(9) . C6 H6C 0.899(9) . C7 H7 0.927(6) . C7 C8 1.3769(13) . C8 H8 0.928(6) . C8 C9 1.3944(12) . C9 C10 1.3954(12) . C10 H10 0.927(6) . C10 C11 1.3782(13) . C11 H11 0.924(7) . C12 H12A 0.899(9) . C12 H12B 0.899(9) . C12 H12C 0.897(9) . 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 O1 H1A Cl2 0.81(2) 2.35(2) 3.1651(9) 173.4(18) 1_455 yes O2 H2A O3 0.83(2) 1.97(2) 2.7969(13) 174.1(18) . yes O2 H2B O1 0.794(17) 2.043(18) 2.8305(14) 171.6(15) . yes O3 H3A Cl1 0.787(19) 2.392(19) 3.1726(10) 171.7(17) . yes O3 H3B Cl2 0.79(2) 2.37(2) 3.1650(10) 175(2) . yes C2 H2 Cl2 0.927(6) 2.595(7) 3.5196(9) 175.2(11) 2_655 yes C4 H4 O2 0.926(6) 2.340(7) 3.2625(12) 174.2(11) . yes C5 H5 Cl2 0.928(6) 2.560(7) 3.4571(9) 162.6(11) 1_455 yes C6 H6A O3 0.900(9) 2.635(12) 3.4545(15) 151.9(15) 4_465 yes C7 H7 O2 0.927(6) 2.467(8) 3.3488(13) 158.9(11) 2_655 yes C8 H8 Cl2 0.928(6) 2.659(7) 3.5791(9) 171.7(11) 2_655 yes C10 H10 O2 0.927(6) 2.495(7) 3.4206(13) 175.7(11) . 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 N1 C1 C2 C3 0.27(14) . . . . N2 C7 C8 C9 -1.00(14) . . . . C1 N1 C5 C4 0.31(14) . . . . C1 C2 C3 C4 0.57(14) . . . . C1 C2 C3 C9 -179.97(9) . . . . C2 C3 C4 C5 -0.98(13) . . . . C2 C3 C9 C8 5.22(14) . . . . C2 C3 C9 C10 -173.93(8) . . . . C3 C4 C5 N1 0.56(14) . . . . C3 C9 C10 C11 177.25(9) . . . . C4 C3 C9 C8 -175.34(8) . . . . C4 C3 C9 C10 5.52(14) . . . . C5 N1 C1 C2 -0.73(14) . . . . C6 N1 C1 C2 178.73(9) . . . . C6 N1 C5 C4 -179.15(9) . . . . C7 N2 C11 C10 1.39(14) . . . . C7 C8 C9 C3 -176.80(9) . . . . C7 C8 C9 C10 2.38(13) . . . . C8 C9 C10 C11 -1.93(14) . . . . C9 C3 C4 C5 179.56(9) . . . . C9 C10 C11 N2 0.09(15) . . . . C11 N2 C7 C8 -0.93(14) . . . . C12 N2 C7 C8 176.07(9) . . . . C12 N2 C11 C10 -175.62(9) . . . . _cod_database_fobs_code 4519451