#------------------------------------------------------------------------------ #$Date: 2023-11-01 18:46:33 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287202 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519453.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_4519453 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, 2(Br), 2(H2 O)' _chemical_formula_sum 'C12 H18 Br2 N2 O2' _chemical_formula_weight 382.10 _chemical_name_common 'Paraquat Dibromide Dihydrate' _chemical_name_systematic ; 1,1'-dimethyl-4,4'-bipyridin-1-ium dibromide 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 difmap _atom_sites_solution_primary dual _cell_angle_alpha 107.877(1) _cell_angle_beta 101.122(1) _cell_angle_gamma 93.657(1) _cell_formula_units_Z 2 _cell_length_a 7.1490(2) _cell_length_b 10.0023(3) _cell_length_c 11.5460(3) _cell_measurement_reflns_used 9225 _cell_measurement_temperature 150 _cell_measurement_theta_max 55.352 _cell_measurement_theta_min 3.591 _cell_volume 764.28(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 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 1.3 (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 0.973 _diffrn_measured_fraction_theta_max 0.974 _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 0.0381 _diffrn_reflns_av_unetI/netI 0.0254 _diffrn_reflns_Laue_measured_fraction_full 0.973 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 19945 _diffrn_reflns_point_group_measured_fraction_full 0.973 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 55.360 _diffrn_reflns_theta_min 3.590 _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 4.444 _exptl_absorpt_correction_T_max 0.2545 _exptl_absorpt_correction_T_min 0.1467 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1304 before and 0.0608 after correction. The Ratio of minimum to maximum transmission is 0.5764. 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 1.660 _exptl_crystal_description irregular _exptl_crystal_F_000 380 _exptl_crystal_recrystallization_method 'seeded with mixed crystal in a saturated solution' _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.385 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.061 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 2879 _refine_ls_number_restraints 7 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0198 _refine_ls_R_factor_gt 0.0195 _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^)+(0.0268P)^2^+0.2576P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.0524 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2817 _reflns_number_total 2879 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S07_Pq-Br2_2H2O_P-1.cif _cod_data_source_block jw23092 _cod_database_code 4519453 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 N1 N 0.26056(18) 0.22509(14) 0.47973(12) 0.0262(3) Uani 1 1 d . . . . . N2 N 0.70254(17) 0.80551(13) 1.00498(12) 0.0253(3) Uani 1 1 d . . . . . C1 C 0.2339(2) 0.35649(18) 0.47957(15) 0.0313(3) Uani 1 1 d . . . . . H1 H 0.169(3) 0.366(2) 0.410(2) 0.037(5) Uiso 1 1 d . . . . . C2 C 0.3129(2) 0.47231(17) 0.58295(15) 0.0306(3) Uani 1 1 d . . . . . H2 H 0.293(3) 0.560(2) 0.5784(18) 0.036(5) Uiso 1 1 d . . . . . C3 C 0.4221(2) 0.45346(15) 0.68993(13) 0.0236(3) Uani 1 1 d . . . . . C4 C 0.4399(2) 0.31507(16) 0.68785(14) 0.0269(3) Uani 1 1 d . . . . . H4 H 0.510(3) 0.294(2) 0.7581(18) 0.028(4) Uiso 1 1 d . . . . . C5 C 0.3598(2) 0.20298(16) 0.58210(15) 0.0286(3) Uani 1 1 d . . . . . H5 H 0.370(3) 0.110(2) 0.5749(17) 0.026(4) Uiso 1 1 d . . . . . C6 C 0.1894(3) 0.10264(19) 0.36461(16) 0.0337(4) Uani 1 1 d . . . . . H6A H 0.110(3) 0.129(2) 0.308(2) 0.043(6) Uiso 1 1 d . . . . . H6B H 0.299(3) 0.071(2) 0.338(2) 0.042(6) Uiso 1 1 d . . . . . H6C H 0.126(3) 0.033(3) 0.386(2) 0.048(6) Uiso 1 1 d . . . . . C7 C 0.7138(2) 0.67319(17) 1.00864(15) 0.0270(3) Uani 1 1 d . . . . . H7 H 0.781(3) 0.6649(19) 1.0814(18) 0.026(4) Uiso 1 1 d . . . . . C8 C 0.6254(2) 0.55773(16) 0.90808(14) 0.0257(3) Uani 1 1 d . . . . . H8 H 0.640(3) 0.471(2) 0.9138(18) 0.033(5) Uiso 1 1 d . . . . . C9 C 0.5186(2) 0.57631(15) 0.80024(13) 0.0236(3) Uani 1 1 d . . . . . C10 C 0.5104(2) 0.71485(16) 0.79958(14) 0.0270(3) Uani 1 1 d . . . . . H10 H 0.448(3) 0.737(2) 0.7341(19) 0.030(5) Uiso 1 1 d . . . . . C11 C 0.6039(2) 0.82699(16) 0.90224(15) 0.0280(3) Uani 1 1 d . . . . . H11 H 0.605(3) 0.919(2) 0.9057(17) 0.027(4) Uiso 1 1 d . . . . . C12 C 0.7896(3) 0.92756(19) 1.11742(17) 0.0336(4) Uani 1 1 d . . . . . H12A H 0.706(4) 0.941(3) 1.171(2) 0.048(6) Uiso 1 1 d . . . . . H12B H 0.898(4) 0.909(3) 1.159(2) 0.054(7) Uiso 1 1 d . . . . . H12C H 0.809(4) 1.001(3) 1.094(2) 0.059(7) Uiso 1 1 d . . . . . Br1 Br 0.25103(2) 0.80266(2) 0.07352(2) 0.02974(8) Uani 1 1 d . . . . . O2 O 0.0356(2) 0.66979(17) 0.25428(13) 0.0450(3) Uani 1 1 d D . . . . H2A H 0.096(3) 0.701(2) 0.2235(18) 0.046(7) Uiso 1 1 d D . . . . H2B H 0.082(4) 0.700(3) 0.3199(14) 0.062(8) Uiso 1 1 d D . . . . Br2 Br 0.25434(2) 0.83189(2) 0.54940(2) 0.03056(8) Uani 1 1 d . . . . . O1 O -0.0027(2) 0.37347(18) 0.22252(14) 0.0508(4) Uani 1 1 d D . . . . H1A H 0.013(3) 0.4457(16) 0.222(2) 0.048(7) Uiso 1 1 d D . . . . H1B H -0.058(4) 0.335(3) 0.1601(16) 0.078(10) 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 N1 0.0258(6) 0.0245(6) 0.0240(6) 0.0040(5) 0.0029(5) -0.0001(5) N2 0.0237(6) 0.0232(6) 0.0244(6) 0.0035(5) 0.0025(5) 0.0012(5) C1 0.0353(8) 0.0295(8) 0.0260(8) 0.0103(6) -0.0015(6) 0.0025(6) C2 0.0367(8) 0.0235(7) 0.0288(8) 0.0094(6) -0.0008(6) 0.0030(6) C3 0.0242(6) 0.0226(7) 0.0235(7) 0.0073(6) 0.0047(5) 0.0019(5) C4 0.0302(7) 0.0246(7) 0.0247(7) 0.0086(6) 0.0026(6) 0.0034(6) C5 0.0321(7) 0.0222(7) 0.0303(8) 0.0082(6) 0.0047(6) 0.0037(6) C6 0.0363(9) 0.0278(8) 0.0279(8) 0.0007(7) 0.0019(7) -0.0017(7) C7 0.0265(7) 0.0280(7) 0.0253(7) 0.0096(6) 0.0018(6) 0.0036(6) C8 0.0294(7) 0.0219(7) 0.0260(7) 0.0089(6) 0.0045(6) 0.0042(5) C9 0.0237(6) 0.0236(7) 0.0229(7) 0.0073(6) 0.0044(5) 0.0023(5) C10 0.0314(7) 0.0240(7) 0.0248(7) 0.0093(6) 0.0018(6) 0.0040(6) C11 0.0310(7) 0.0221(7) 0.0299(8) 0.0086(6) 0.0040(6) 0.0040(6) C12 0.0354(9) 0.0259(8) 0.0295(8) 0.0008(7) -0.0023(7) 0.0026(7) Br1 0.03278(11) 0.02693(11) 0.03043(11) 0.01146(7) 0.00546(7) 0.00471(7) O2 0.0425(7) 0.0564(9) 0.0334(7) 0.0187(6) 0.0004(6) -0.0074(6) Br2 0.03384(11) 0.02760(11) 0.03095(11) 0.01233(7) 0.00435(7) 0.00411(7) O1 0.0580(9) 0.0531(9) 0.0374(8) 0.0216(7) -0.0064(6) -0.0027(7) 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' 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 C1 N1 C5 120.84(13) . . C1 N1 C6 120.17(14) . . C5 N1 C6 118.92(14) . . C7 N2 C12 119.52(14) . . C11 N2 C7 120.36(13) . . C11 N2 C12 120.01(14) . . N1 C1 H1 117.9(13) . . N1 C1 C2 120.74(15) . . C2 C1 H1 121.3(13) . . C1 C2 H2 117.9(13) . . C1 C2 C3 119.93(15) . . C3 C2 H2 122.2(13) . . C2 C3 C9 121.29(13) . . C4 C3 C2 117.44(13) . . C4 C3 C9 121.25(13) . . C3 C4 H4 121.9(11) . . C5 C4 C3 120.43(14) . . C5 C4 H4 117.6(11) . . N1 C5 C4 120.54(14) . . N1 C5 H5 115.5(12) . . C4 C5 H5 124.0(12) . . N1 C6 H6A 110.0(14) . . N1 C6 H6B 105.7(14) . . N1 C6 H6C 107.7(15) . . H6A C6 H6B 113(2) . . H6A C6 H6C 111(2) . . H6B C6 H6C 110(2) . . N2 C7 H7 116.6(12) . . N2 C7 C8 120.94(14) . . C8 C7 H7 122.4(12) . . C7 C8 H8 117.9(12) . . C7 C8 C9 120.21(14) . . C9 C8 H8 121.9(13) . . C8 C9 C3 121.40(13) . . C10 C9 C3 121.29(13) . . C10 C9 C8 117.30(13) . . C9 C10 H10 123.4(12) . . C11 C10 C9 120.21(14) . . C11 C10 H10 116.4(12) . . N2 C11 C10 120.97(14) . . N2 C11 H11 115.5(12) . . C10 C11 H11 123.5(12) . . N2 C12 H12A 108.0(15) . . N2 C12 H12B 110.9(16) . . N2 C12 H12C 108.0(17) . . H12A C12 H12B 106(2) . . H12A C12 H12C 112(2) . . H12B C12 H12C 112(2) . . H2A O2 H2B 104(2) . . H1A O1 H1B 104(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C1 1.340(2) . N1 C5 1.344(2) . N1 C6 1.4784(19) . N2 C7 1.344(2) . N2 C11 1.343(2) . N2 C12 1.4770(19) . C1 H1 0.89(2) . C1 C2 1.376(2) . C2 H2 0.91(2) . C2 C3 1.400(2) . C3 C4 1.391(2) . C3 C9 1.483(2) . C4 H4 0.95(2) . C4 C5 1.373(2) . C5 H5 0.91(2) . C6 H6A 0.89(3) . C6 H6B 0.93(2) . C6 H6C 0.93(3) . C7 H7 0.91(2) . C7 C8 1.372(2) . C8 H8 0.90(2) . C8 C9 1.401(2) . C9 C10 1.393(2) . C10 H10 0.89(2) . C10 C11 1.376(2) . C11 H11 0.91(2) . C12 H12A 0.92(3) . C12 H12B 0.89(3) . C12 H12C 0.87(3) . O2 H2A 0.726(14) . O2 H2B 0.725(14) . O1 H1A 0.724(14) . O1 H1B 0.724(14) . 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 0.89(2) 2.29(2) 3.179(2) 175.6(18) . yes C7 H7 O2 0.91(2) 2.41(2) 3.300(2) 163.5(15) 1_656 yes O2 H2A Br1 0.726(14) 2.630(15) 3.3431(15) 168(2) . yes O2 H2B Br2 0.725(14) 2.581(15) 3.3035(14) 174(3) . yes O1 H1A O2 0.724(14) 2.148(15) 2.861(2) 169(3) . yes O1 H1B Br1 0.724(14) 2.668(14) 3.3914(15) 178(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 N1 C1 C2 C3 -0.2(3) . . . . N2 C7 C8 C9 -1.2(2) . . . . C1 N1 C5 C4 -1.6(2) . . . . C1 C2 C3 C4 -2.3(2) . . . . C1 C2 C3 C9 176.43(15) . . . . C2 C3 C4 C5 2.9(2) . . . . C2 C3 C9 C8 179.00(15) . . . . C2 C3 C9 C10 -2.6(2) . . . . C3 C4 C5 N1 -1.0(2) . . . . C3 C9 C10 C11 -178.84(14) . . . . C4 C3 C9 C8 -2.3(2) . . . . C4 C3 C9 C10 176.09(14) . . . . C5 N1 C1 C2 2.1(2) . . . . C6 N1 C1 C2 -174.67(16) . . . . C6 N1 C5 C4 175.29(15) . . . . C7 N2 C11 C10 0.9(2) . . . . C7 C8 C9 C3 179.77(14) . . . . C7 C8 C9 C10 1.3(2) . . . . C8 C9 C10 C11 -0.4(2) . . . . C9 C3 C4 C5 -175.85(14) . . . . C9 C10 C11 N2 -0.7(2) . . . . C11 N2 C7 C8 0.1(2) . . . . C12 N2 C7 C8 176.41(15) . . . . C12 N2 C11 C10 -175.43(15) . . . . _cod_database_fobs_code 4519453