#------------------------------------------------------------------------------ #$Date: 2023-11-01 18:38:56 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287198 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519449.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_4519449 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(Cl), 2.63(H2 O)' _chemical_formula_sum 'C12 H19.26 Cl2 N2 O2.63' _chemical_formula_weight 304.53 _chemical_name_common 'Paraquat Dichloride Hydrate' _chemical_name_systematic ; 1,1'-dimethyl-4,4'-bipyridin-1-ium bis(chloride) hydrate ; _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_Hall '-P 2ac 2n' _space_group_name_H-M_alt 'P n m a' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.1413(4) _cell_length_b 10.7906(5) _cell_length_c 15.9990(7) _cell_measurement_reflns_used 7396 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.861 _cell_measurement_theta_min 4.301 _cell_volume 1578.14(12) _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 0.989 _diffrn_measured_fraction_theta_max 0.977 _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 0.0596 _diffrn_reflns_av_unetI/netI 0.0186 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1550 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.882 _diffrn_reflns_theta_min 4.300 _diffrn_source 'Metal Jet' _diffrn_source_current 2.85 _diffrn_source_power 0.198759 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.74 _exptl_absorpt_coefficient_mu 2.471 _exptl_absorpt_correction_T_max 0.751 _exptl_absorpt_correction_T_min 0.589 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. Final HKLF 4 output contains 52164 reflections, Rint = 0.0596 (15051 with I > 3sig(I), Rint = 0.0501) ; _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 1.282 _exptl_crystal_description Plate _exptl_crystal_F_000 641 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.485 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.072 _refine_ls_extinction_coef 0.0049(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 108 _refine_ls_number_reflns 1550 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.099 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0487 _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^)+(0.0717P)^2^+1.9139P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1341 _refine_ls_wR_factor_ref 0.1371 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1480 _reflns_number_total 1550 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S02_Pq-Cl2_2_63H2O_Pnma.cif _cod_data_source_block jw25161 _cod_database_code 4519449 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z' 4 'x+1/2, -y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z' 8 '-x-1/2, 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 N1 N 0.8258(2) 0.5173(2) 0.61453(12) 0.0318(5) Uani 1 1 d . . . . . C1 C 0.7081(3) 0.5810(2) 0.63992(15) 0.0334(6) Uani 1 1 d . . . . . H1 H 0.714396 0.631034 0.688636 0.040 Uiso 1 1 calc R U . . . C2 C 0.5791(3) 0.5751(2) 0.59678(14) 0.0307(5) Uani 1 1 d . . . . . H2 H 0.496345 0.619955 0.616147 0.037 Uiso 1 1 calc R U . . . C3 C 0.5687(2) 0.5033(2) 0.52422(13) 0.0252(5) Uani 1 1 d . . . . . C4 C 0.6937(3) 0.4383(2) 0.49988(15) 0.0310(6) Uani 1 1 d . . . . . H4 H 0.691294 0.388231 0.451079 0.037 Uiso 1 1 calc R U . . . C5 C 0.8196(3) 0.4463(2) 0.54578(16) 0.0337(6) Uani 1 1 d . . . . . H5 H 0.903599 0.401128 0.528756 0.040 Uiso 1 1 calc R U . . . C6 C 0.9658(3) 0.5320(3) 0.65951(19) 0.0510(8) Uani 1 1 d . . . . . H6A H 1.011903 0.610255 0.642941 0.077 Uiso 1 1 calc R U . . . H6B H 1.030936 0.462876 0.645541 0.077 Uiso 1 1 calc R U . . . H6C H 0.947621 0.532658 0.719866 0.077 Uiso 1 1 calc R U . . . Cl1 Cl 0.88196(9) 0.750000 0.47110(6) 0.0414(3) Uani 1 2 d S T P . . Cl2 Cl 0.77671(8) 0.750000 0.81944(4) 0.0241(3) Uani 1 2 d S T P . . O2W O 0.8003(11) 0.1472(7) 0.8173(6) 0.143(6) Uani 0.435(11) 1 d . . P A 2 H2WA H 0.745370 0.172185 0.858398 0.214 Uiso 0.435(11) 1 d R U P A 2 H2WB H 0.794790 0.066725 0.819145 0.214 Uiso 0.435(11) 1 d R U P A 2 O4W O 0.433(3) 0.250000 0.5878(16) 0.149(4) Uani 0.298(9) 2 d S T P B 1 H4WA H 0.407459 0.299680 0.628174 0.223 Uiso 0.149(4) 1 d R U P B 1 H4WB H 0.522689 0.272970 0.581207 0.223 Uiso 0.149(4) 1 d R U P B 1 O5W O 0.5085(16) 0.250000 0.6784(6) 0.202(8) Uani 0.761(18) 2 d S T P C 3 H5WA H 0.426054 0.209640 0.678166 0.304 Uiso 0.380(9) 1 d R U P C 3 H5WB H 0.517294 0.278000 0.627319 0.304 Uiso 0.380(9) 1 d R U P C 3 O3W O 0.3672(12) 0.250000 0.7173(7) 0.149(4) Uani 0.702(9) 2 d S T P B 1 H3WA H 0.333610 0.321540 0.701508 0.223 Uiso 0.351(4) 1 d R U P B 1 H3WB H 0.417530 0.262330 0.763062 0.223 Uiso 0.351(4) 1 d R U P B 1 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 0.0248(10) 0.0401(12) 0.0306(10) -0.0092(9) -0.0022(8) -0.0009(9) C1 0.0321(13) 0.0388(13) 0.0294(12) -0.0132(10) -0.0019(10) 0.0009(10) C2 0.0284(12) 0.0340(12) 0.0296(11) -0.0105(10) -0.0016(9) 0.0029(10) C3 0.0257(12) 0.0242(11) 0.0259(11) -0.0047(9) 0.0021(9) -0.0016(9) C4 0.0273(12) 0.0343(13) 0.0315(12) -0.0127(10) 0.0000(9) 0.0013(10) C5 0.0268(12) 0.0390(14) 0.0352(12) -0.0118(11) 0.0007(10) 0.0038(10) C6 0.0274(14) 0.077(2) 0.0490(16) -0.0257(16) -0.0110(12) 0.0040(14) Cl1 0.0295(5) 0.0408(5) 0.0541(6) 0.000 0.0048(4) 0.000 Cl2 0.0272(5) 0.0262(4) 0.0189(4) 0.000 -0.0032(3) 0.000 O2W 0.179(10) 0.062(5) 0.187(10) -0.040(5) 0.125(8) -0.050(5) O4W 0.144(8) 0.158(9) 0.144(8) 0.000 -0.048(7) 0.000 O5W 0.327(19) 0.131(8) 0.148(9) 0.000 0.159(11) 0.000 O3W 0.144(8) 0.158(9) 0.144(8) 0.000 -0.048(7) 0.000 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 C1 N1 C5 120.5(2) . . C1 N1 C6 119.5(2) . . C5 N1 C6 119.8(2) . . N1 C1 H1 119.5 . . N1 C1 C2 121.0(2) . . C2 C1 H1 119.5 . . C1 C2 H2 119.9 . . C1 C2 C3 120.2(2) . . C3 C2 H2 119.9 . . C2 C3 C3 121.3(3) . 5_666 C4 C3 C2 117.0(2) . . C4 C3 C3 121.7(2) . 5_666 C3 C4 H4 119.8 . . C5 C4 C3 120.5(2) . . C5 C4 H4 119.8 . . N1 C5 C4 120.8(2) . . N1 C5 H5 119.6 . . C4 C5 H5 119.6 . . 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 . . H2WA O2W H2WB 104.5 . . H4WA O4W H4WA 76.0 . 7_565 H4WA O4W H4WB 99.6 . . H4WA O4W H4WB 99.6 7_565 7_565 H4WA O4W H4WB 121.4 . 7_565 H4WA O4W H5WB 64.5 7_565 7_565 H4WA O4W H5WB 85.8 . 7_565 H4WB O4W H4WA 121.4 . 7_565 H4WB O4W H4WB 33.3 . 7_565 H4WB O4W H5WB 44.6 7_565 7_565 H4WB O4W H5WB 56.9 . 7_565 H4WA O5W H5WA 66.4 7_565 7_565 H4WA O5W H5WB 50.5 7_565 7_565 H5WA O5W H5WB 104.4 . . H5WA O3W H3WB 109.3 7_565 7_565 H3WA O3W H5WA 66.1 . 7_565 H3WA O3W H3WA 125.5 . 7_565 H3WA O3W H3WB 107.1 7_565 7_565 H3WA O3W H3WB 124.4 . 7_565 H3WA O3W H3WB 107.1 . . H3WB O3W H5WA 100.8 . 7_565 H3WB O3W H3WA 124.4 . 7_565 H3WB O3W H3WB 17.5 . 7_565 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C1 1.339(3) . N1 C5 1.341(3) . N1 C6 1.478(3) . C1 H1 0.9500 . C1 C2 1.368(3) . C2 H2 0.9500 . C2 C3 1.399(3) . C3 C3 1.478(4) 5_666 C3 C4 1.395(3) . C4 H4 0.9500 . C4 C5 1.368(3) . C5 H5 0.9500 . C6 H6A 0.9800 . C6 H6B 0.9800 . C6 H6C 0.9800 . O2W H2WA 0.8703 . O2W H2WB 0.8699 . O4W H4WA 0.8708 7_565 O4W H4WA 0.8707 . O4W H4WB 0.8644 7_565 O4W H4WB 0.8644 . O4W H5WB 1.04(2) 7_565 O5W H5WA 0.8702 . O5W H5WA 0.8701 7_565 O5W H5WB 0.8751 7_565 O5W H5WB 0.8751 . O3W H3WA 0.8684 . O3W H3WA 0.8684 7_565 O3W H3WB 0.8750 7_565 O3W H3WB 0.8750 . 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 -0.9(4) . . . . C1 N1 C5 C4 0.5(4) . . . . C1 C2 C3 C3 -179.1(3) . . . 5_666 C1 C2 C3 C4 0.9(4) . . . . C2 C3 C4 C5 -0.2(4) . . . . C3 C3 C4 C5 179.8(3) 5_666 . . . C3 C4 C5 N1 -0.5(4) . . . . C5 N1 C1 C2 0.2(4) . . . . C6 N1 C1 C2 176.1(3) . . . . C6 N1 C5 C4 -175.4(3) . . . . _cod_database_fobs_code 4519449