#------------------------------------------------------------------------------ #$Date: 2023-11-01 18:34:29 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287197 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519448.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_4519448 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)' _chemical_formula_sum 'C12 H14 Cl2 N2' _chemical_formula_weight 257.15 _chemical_name_common 'Paraquat Dichloride' _chemical_name_systematic ; 1,1'-dimethyl-4,4'-bipyridin-1-ium bis(chloride) ; _space_group_crystal_system orthorhombic _space_group_IT_number 58 _space_group_name_Hall '-P 2 2n' _space_group_name_H-M_alt 'P n n m' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 13.7562(6) _cell_length_b 6.3270(3) _cell_length_c 7.1050(3) _cell_measurement_reflns_used 4917 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.894 _cell_measurement_theta_min 5.598 _cell_volume 618.39(5) _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 1.3 (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 0.992 _diffrn_measured_fraction_theta_max 0.992 _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 0.0380 _diffrn_reflns_av_unetI/netI 0.0277 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 5169 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.868 _diffrn_reflns_theta_min 5.596 _diffrn_source 'Metal Jet' _diffrn_source_current 2.85 _diffrn_source_power 0.1986735 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.71 _exptl_absorpt_coefficient_mu 2.988 _exptl_absorpt_correction_T_max 0.2536 _exptl_absorpt_correction_T_min 0.1515 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1325 before and 0.0606 after correction. The Ratio of minimum to maximum transmission is 0.5974. 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 1.381 _exptl_crystal_description block _exptl_crystal_F_000 268 _exptl_crystal_recrystallization_method 'crystallised from EtOH 95%' _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.204 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 58 _refine_ls_number_reflns 639 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.136 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0301 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.1800P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0857 _refine_ls_wR_factor_ref 0.0865 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 622 _reflns_number_total 639 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S01_Pq-Cl2_Anhydre_Pnnm.cif _cod_data_source_block jw25587 _cod_database_code 4519448 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z' 3 '-x+1/2, y+1/2, -z+1/2' 4 'x+1/2, -y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, y, -z' 7 'x-1/2, -y-1/2, z-1/2' 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 C1 C 0.38782(13) 0.6237(3) 0.6629(2) 0.0472(4) Uani 1 1 d . . . . . H1 H 0.3687(14) 0.553(4) 0.768(3) 0.073(7) Uiso 1 1 d . . . . . N1 N 0.36251(10) 0.5340(3) 0.500000 0.0320(4) Uani 1 2 d S T P . . C2 C 0.44111(13) 0.8079(3) 0.6662(2) 0.0470(4) Uani 1 1 d . . . . . H2 H 0.4601(15) 0.856(3) 0.780(3) 0.073(6) Uiso 1 1 d . . . . . C3 C 0.46985(12) 0.9024(3) 0.500000 0.0299(4) Uani 1 2 d S T P . . C4 C 0.30340(15) 0.3384(3) 0.500000 0.0385(5) Uani 1 2 d S T P . . H4A H 0.2356(18) 0.383(4) 0.500000 0.042(6) Uiso 1 2 d S . P . . H4B H 0.3172(13) 0.262(2) 0.384(3) 0.043(5) Uiso 1 1 d . . . . . Cl1 Cl 0.13369(4) 0.73373(8) 0.500000 0.0402(2) Uani 1 2 d S T P . . 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 C1 0.0663(10) 0.0394(9) 0.0358(8) 0.0064(7) -0.0025(7) -0.0150(7) N1 0.0310(8) 0.0252(8) 0.0399(9) 0.000 0.000 0.0029(6) C2 0.0683(10) 0.0395(8) 0.0333(8) 0.0039(7) -0.0077(7) -0.0163(7) C3 0.0297(8) 0.0259(9) 0.0342(9) 0.000 0.000 0.0047(7) C4 0.0365(10) 0.0260(10) 0.0530(13) 0.000 0.000 -0.0017(8) Cl1 0.0484(4) 0.0350(3) 0.0373(4) 0.000 0.000 0.01124(18) 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' 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 115.3(14) . . N1 C1 C2 120.88(14) . . C2 C1 H1 123.9(14) . . C1 N1 C1 120.17(18) 6_556 . C1 N1 C4 119.90(9) 6_556 . C1 N1 C4 119.90(9) . . C1 C2 H2 117.0(14) . . C1 C2 C3 120.28(14) . . C3 C2 H2 122.5(14) . . C2 C3 C2 117.49(18) . 6_556 C2 C3 C3 121.25(9) . 5_676 C2 C3 C3 121.25(9) 6_556 5_676 N1 C4 H4A 106.4(14) . . N1 C4 H4B 107.9(10) . . N1 C4 H4B 107.9(10) . 6_556 H4A C4 H4B 109.4(12) . . H4A C4 H4B 109.3(12) . 6_556 H4B C4 H4B 116(2) . 6_556 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 H1 0.91(2) . C1 N1 1.3355(18) . C1 C2 1.377(2) . N1 C4 1.480(2) . C2 H2 0.91(2) . C2 C3 1.3813(18) . C3 C3 1.488(4) 5_676 C4 H4A 0.98(2) . C4 H4B 0.971(19) . C4 H4B 0.971(19) 6_556 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 0.91(2) 2.61(2) 3.4514(16) 154.7(18) 3_546 yes C2 H2 Cl1 0.91(2) 2.91(2) 3.5654(17) 130.6(17) 7_676 yes C4 H4A Cl1 0.98(2) 2.62(2) 3.421(2) 139.2(18) . yes C4 H4B Cl1 0.971(19) 2.82(2) 3.7159(6) 154.0(12) 3_545 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 C2 C3 C2 1.5(3) . . . 6_556 C1 C2 C3 C3 -178.0(2) . . . 5_676 N1 C1 C2 C3 -0.4(3) . . . . C2 C1 N1 C1 -0.8(3) . . . 6_556 C2 C1 N1 C4 -178.70(17) . . . . _cod_database_fobs_code 4519448