#------------------------------------------------------------------------------ #$Date: 2023-11-01 18:45:12 +0000 (Wed, 01 Nov 2023) $ #$Revision: 287201 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519452.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_4519452 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)' _chemical_formula_sum 'C12 H14 Br2 N2' _chemical_formula_weight 346.07 _chemical_name_common 'Paraquat Dibromide' _chemical_name_systematic ; 1,1'-dimethyl-4,4'-bipyridin-1-ium dibromide ; _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 96.191(1) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.9183(2) _cell_length_b 8.0344(2) _cell_length_c 13.4237(4) _cell_measurement_reflns_used 9989 _cell_measurement_temperature 100 _cell_measurement_theta_max 71.667 _cell_measurement_theta_min 3.312 _cell_volume 634.57(3) _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 100 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.3 _diffrn_detector_type 'Bruker APEX2 CCD' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Quazar MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_unetI/netI 0.0118 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 12462 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 71.660 _diffrn_reflns_theta_min 6.430 _diffrn_source 'Microfocus Source' _diffrn_source_current 0.65 _diffrn_source_power 0.02912 _diffrn_source_target Cu _diffrn_source_type 'Incoatec I\mS High Brilliance Microsource' _diffrn_source_voltage 44.8 _exptl_absorpt_coefficient_mu 7.890 _exptl_absorpt_correction_T_max 0.2768 _exptl_absorpt_correction_T_min 0.1338 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1558 before and 0.0346 after correction. The Ratio of minimum to maximum transmission is 0.4834. 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 1.811 _exptl_crystal_description needle _exptl_crystal_F_000 340 _exptl_crystal_recrystallization_method 'crystallized from H2O / DMSO on a microscope plate' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.328 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.065 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 1236 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.154 _refine_ls_R_factor_all 0.0188 _refine_ls_R_factor_gt 0.0188 _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^)+(0.0286P)^2^+0.4194P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.0510 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1235 _reflns_number_total 1236 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file S06_Pq-Br2_P21_c.cif _cod_data_source_block jw22651 _cod_database_code 4519452 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 Br1 Br 0.82431(3) 0.41719(2) 0.32455(2) 0.02088(10) Uani 1 1 d . . . . . N1 N 0.5165(3) 0.75575(18) 0.43162(11) 0.0186(3) Uani 1 1 d . . . . . H1 H 0.491(4) 0.744(3) 0.5713(18) 0.021(6) Uiso 1 1 d . . . . . H5 H 0.580(4) 0.795(3) 0.2959(18) 0.023(5) Uiso 1 1 d . . . . . C1 C 0.5802(3) 0.7878(2) 0.52928(14) 0.0198(3) Uani 1 1 d . . . . . H2 H 0.809(4) 0.901(3) 0.627(2) 0.028(6) Uiso 1 1 d . . . . . C2 C 0.7689(3) 0.8826(2) 0.55800(14) 0.0197(4) Uani 1 1 d . . . . . C3 C 0.8973(3) 0.9489(2) 0.48564(14) 0.0183(4) Uani 1 1 d . . . . . C4 C 0.8243(3) 0.9155(2) 0.38507(15) 0.0207(4) Uani 1 1 d . . . . . H4 H 0.904(4) 0.955(3) 0.3362(19) 0.025(6) Uiso 1 1 d . . . . . C5 C 0.6367(3) 0.8170(2) 0.36036(14) 0.0214(4) Uani 1 1 d . . . . . C6 C 0.3176(3) 0.6478(2) 0.40152(15) 0.0220(4) Uani 1 1 d . . . . . H6A H 0.223(4) 0.705(3) 0.3511(18) 0.023(6) Uiso 1 1 d . . . . . H6B H 0.366(5) 0.550(3) 0.375(2) 0.031(7) Uiso 1 1 d . . . . . H6C H 0.237(4) 0.624(3) 0.4569(19) 0.025(6) Uiso 1 1 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 0.02194(14) 0.02288(14) 0.01833(13) -0.00029(6) 0.00452(8) -0.00161(6) N1 0.0193(7) 0.0165(7) 0.0201(7) 0.0003(6) 0.0025(6) 0.0011(6) C1 0.0228(9) 0.0179(8) 0.0192(8) 0.0028(7) 0.0039(7) 0.0015(7) C2 0.0236(9) 0.0185(8) 0.0169(9) 0.0021(7) 0.0019(7) 0.0010(7) C3 0.0200(9) 0.0166(8) 0.0187(9) 0.0011(7) 0.0038(7) 0.0044(7) C4 0.0215(9) 0.0229(9) 0.0184(9) 0.0011(6) 0.0050(7) 0.0007(7) C5 0.0232(9) 0.0233(9) 0.0179(8) -0.0006(7) 0.0027(7) 0.0012(7) C6 0.0219(9) 0.0211(9) 0.0232(9) 0.0002(7) 0.0028(7) -0.0023(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 C6 120.46(15) . . C5 N1 C1 120.48(16) . . C5 N1 C6 119.03(15) . . N1 C1 H1 114.6(15) . . N1 C1 C2 120.85(17) . . C2 C1 H1 124.5(15) . . C1 C2 H2 118.4(16) . . C1 C2 C3 120.13(17) . . C3 C2 H2 121.5(16) . . C2 C3 C3 121.4(2) . 3_776 C4 C3 C2 117.53(17) . . C4 C3 C3 121.1(2) . 3_776 C3 C4 H4 120.1(17) . . C5 C4 C3 120.03(18) . . C5 C4 H4 119.8(16) . . N1 C5 H5 115.7(15) . . N1 C5 C4 120.95(17) . . C4 C5 H5 123.2(15) . . N1 C6 H6A 107.5(14) . . N1 C6 H6B 109.4(17) . . N1 C6 H6C 111.0(15) . . H6A C6 H6B 109(2) . . H6A C6 H6C 110(2) . . H6B C6 H6C 110(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C1 1.349(2) . N1 C5 1.345(2) . N1 C6 1.483(2) . C1 H1 0.89(2) . C1 C2 1.372(3) . C2 H2 0.94(3) . C2 C3 1.402(3) . C3 C3 1.483(4) 3_776 C3 C4 1.398(3) . C4 H4 0.90(3) . C4 C5 1.375(3) . C5 H5 0.91(2) . C6 H6A 0.95(3) . C6 H6B 0.92(3) . C6 H6C 0.95(3) . 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 0.6(3) . . . . C1 N1 C5 C4 -1.0(3) . . . . C1 C2 C3 C3 -179.7(2) . . . 3_776 C1 C2 C3 C4 0.4(3) . . . . C2 C3 C4 C5 -1.8(3) . . . . C3 C3 C4 C5 178.4(2) 3_776 . . . C3 C4 C5 N1 2.1(3) . . . . C5 N1 C1 C2 -0.3(3) . . . . C6 N1 C1 C2 177.62(17) . . . . C6 N1 C5 C4 -179.02(17) . . . . _cod_database_fobs_code 4519452