#------------------------------------------------------------------------------
#$Date: 2023-11-01 21:20:55 +0200 (Wed, 01 Nov 2023) $
#$Revision: 287221 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/94/4519472.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_4519472
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, 0.984(Br), 1.016(Cl), 2(H2 O)'
_chemical_formula_sum            'C12 H18 Br0.98 Cl1.02 N2 O2'
_chemical_formula_weight         336.98
_chemical_name_common
;
Paraquat Bromide Chloride 0.98:1.02 Dihydrate
;
_chemical_name_systematic
;
1,1'-dimethyl-4,4'-bipyridin-1-ium bromide chloride 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   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                107.616(1)
_cell_angle_beta                 100.811(1)
_cell_angle_gamma                93.396(1)
_cell_formula_units_Z            2
_cell_length_a                   7.0732(2)
_cell_length_b                   9.8786(3)
_cell_length_c                   11.4345(3)
_cell_measurement_reflns_used    6366
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.915
_cell_measurement_theta_min      3.615
_cell_volume                     742.22(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 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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_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 0.951
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ 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  0.0213
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6830
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.940
_diffrn_reflns_theta_min         3.614
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    3.570
_exptl_absorpt_correction_T_max  0.1123
_exptl_absorpt_correction_T_min  0.0356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0782 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.3170.
The λ/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    1.508
_exptl_crystal_description       Bock
_exptl_crystal_F_000             343
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2650
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0273
_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/[σ²(Fo²)+(0.0204P)²+0.5281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2537
_reflns_number_total             2650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            S26_Pq-Br_0_98_Cl_1_02_2H2O_P-1.cif
_cod_data_source_block           jw25533
_cod_database_code               4519472
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
Br1 Br -0.2531(13) 0.1971(9) -0.0716(7) 0.0410(5) Uani 0.492(3) 1 d . . P A 1
Br2 Br 0.2573(8) 0.8308(6) 0.5511(3) 0.0363(4) Uani 0.492(3) 1 d . . P A 1
Cl1 Cl -0.255(3) 0.204(2) -0.0788(17) 0.0410(5) Uani 0.508(3) 1 d . . P A 2
Cl2 Cl 0.2488(19) 0.8291(13) 0.5337(8) 0.0363(4) Uani 0.508(3) 1 d . . P A 2
C1 C 0.2302(3) 0.3567(2) 0.4787(2) 0.0449(5) Uani 1 1 d . . . . .
H1 H 0.155446 0.370555 0.405994 0.054 Uiso 1 1 calc R U . . .
N1 N 0.2560(3) 0.2237(2) 0.47968(17) 0.0404(4) Uani 1 1 d . . . . .
C2 C 0.3106(3) 0.4732(2) 0.5818(2) 0.0439(5) Uani 1 1 d . . . . .
H2 H 0.292130 0.566994 0.579853 0.053 Uiso 1 1 calc R U . . .
N2 N 0.7048(3) 0.80836(19) 1.00326(17) 0.0393(4) Uani 1 1 d . . . . .
C3 C 0.4194(3) 0.4538(2) 0.6895(2) 0.0367(5) Uani 1 1 d . . . . .
C4 C 0.4360(3) 0.3139(2) 0.6884(2) 0.0400(5) Uani 1 1 d . . . . .
H4 H 0.504001 0.296473 0.761384 0.048 Uiso 1 1 calc R U . . .
C5 C 0.3551(3) 0.2011(2) 0.5831(2) 0.0420(5) Uani 1 1 d . . . . .
H5 H 0.369131 0.106043 0.583077 0.050 Uiso 1 1 calc R U . . .
C6 C 0.1832(4) 0.1002(3) 0.3647(2) 0.0499(6) Uani 1 1 d . . . . .
H6A H 0.099091 0.131306 0.301888 0.075 Uiso 1 1 calc R U . . .
H6B H 0.109286 0.026438 0.385016 0.075 Uiso 1 1 calc R U . . .
H6C H 0.293063 0.060788 0.331048 0.075 Uiso 1 1 calc R U . . .
C7 C 0.6052(3) 0.8303(2) 0.9003(2) 0.0413(5) Uani 1 1 d . . . . .
H7 H 0.600507 0.925346 0.897750 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5095(3) 0.7174(2) 0.7981(2) 0.0404(5) Uani 1 1 d . . . . .
H8 H 0.438016 0.735024 0.726185 0.048 Uiso 1 1 calc R U . . .
C9 C 0.5170(3) 0.5776(2) 0.7997(2) 0.0372(5) Uani 1 1 d . . . . .
C10 C 0.6253(3) 0.5585(2) 0.9077(2) 0.0388(5) Uani 1 1 d . . . . .
H10 H 0.636029 0.464528 0.911677 0.047 Uiso 1 1 calc R U . . .
C11 C 0.7162(3) 0.6744(2) 1.0080(2) 0.0401(5) Uani 1 1 d . . . . .
H11 H 0.787754 0.660039 1.081481 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7963(4) 0.9310(3) 1.1150(2) 0.0494(6) Uani 1 1 d . . . . .
H12A H 0.807882 1.017659 1.090773 0.074 Uiso 1 1 calc R U . . .
H12B H 0.925514 0.912300 1.150471 0.074 Uiso 1 1 calc R U . . .
H12C H 0.716182 0.944389 1.177923 0.074 Uiso 1 1 calc R U . . .
O1 O -0.0098(3) 0.3687(3) 0.2158(2) 0.0647(5) Uani 1 1 d D . . . .
H1A H -0.074(5) 0.322(4) 0.145(3) 0.104(15) Uiso 1 1 d D . . . .
H1B H 0.017(5) 0.453(3) 0.221(3) 0.086(12) Uiso 1 1 d D . . . .
O2 O 0.0433(3) 0.6702(2) 0.2548(2) 0.0622(5) Uani 1 1 d D . . . .
H2A H 0.092(5) 0.708(4) 0.331(2) 0.088(12) Uiso 1 1 d D . . . .
H2B H 0.109(5) 0.711(4) 0.220(3) 0.087(12) Uiso 1 1 d D . . . .
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'
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
N1 C1 H1 119.7 . .
N1 C1 C2 120.7(2) . .
C2 C1 H1 119.7 . .
C1 N1 C5 120.7(2) . .
C1 N1 C6 120.2(2) . .
C5 N1 C6 119.0(2) . .
C1 C2 H2 120.0 . .
C1 C2 C3 120.1(2) . .
C3 C2 H2 120.0 . .
C7 N2 C11 120.48(19) . .
C7 N2 C12 120.26(19) . .
C11 N2 C12 119.2(2) . .
C2 C3 C9 121.3(2) . .
C4 C3 C2 117.4(2) . .
C4 C3 C9 121.3(2) . .
C3 C4 H4 119.8 . .
C5 C4 C3 120.5(2) . .
C5 C4 H4 119.8 . .
N1 C5 C4 120.6(2) . .
N1 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
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 . .
N2 C7 H7 119.5 . .
N2 C7 C8 121.0(2) . .
C8 C7 H7 119.5 . .
C7 C8 H8 119.9 . .
C7 C8 C9 120.2(2) . .
C9 C8 H8 119.9 . .
C8 C9 C3 121.3(2) . .
C8 C9 C10 117.2(2) . .
C10 C9 C3 121.4(2) . .
C9 C10 H10 119.7 . .
C11 C10 C9 120.5(2) . .
C11 C10 H10 119.7 . .
N2 C11 C10 120.5(2) . .
N2 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
N2 C12 H12A 109.5 . .
N2 C12 H12B 109.5 . .
N2 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
H1A O1 H1B 111(4) . .
H2A O2 H2B 104(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9500 .
C1 N1 1.340(3) .
C1 C2 1.374(3) .
N1 C5 1.344(3) .
N1 C6 1.477(3) .
C2 H2 0.9500 .
C2 C3 1.396(3) .
N2 C7 1.338(3) .
N2 C11 1.348(3) .
N2 C12 1.476(3) .
C3 C4 1.391(3) .
C3 C9 1.484(3) .
C4 H4 0.9500 .
C4 C5 1.369(3) .
C5 H5 0.9500 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 H7 0.9500 .
C7 C8 1.376(3) .
C8 H8 0.9500 .
C8 C9 1.391(3) .
C9 C10 1.396(3) .
C10 H10 0.9500 .
C10 C11 1.372(3) .
C11 H11 0.9500 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
O1 H1A 0.83(2) .
O1 H1B 0.82(2) .
O2 H2A 0.84(2) .
O2 H2B 0.83(2) .
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 0.95 2.26 3.204(3) 170.7 . yes
C2 H2 Br2 0.95 2.74 3.689(6) 173.6 . yes
C2 H2 Cl2 0.95 2.82 3.758(12) 170.5 . yes
C4 H4 Br1 0.95 2.77 3.695(9) 164.9 1_656 yes
C4 H4 Cl1 0.95 2.67 3.59(2) 164.3 1_656 yes
C5 H5 Br2 0.95 2.68 3.576(6) 157.3 1_545 yes
C5 H5 Cl2 0.95 2.67 3.556(13) 155.2 1_545 yes
C7 H7 Br1 0.95 2.71 3.602(9) 155.9 1_666 yes
C7 H7 Cl1 0.95 2.79 3.68(2) 157.0 1_666 yes
C8 H8 Br2 0.95 2.62 3.560(5) 170.0 . yes
C8 H8 Cl2 0.95 2.79 3.731(10) 171.5 . yes
C10 H10 Br1 0.95 2.85 3.787(9) 168.8 1_656 yes
C10 H10 Cl1 0.95 2.76 3.70(2) 168.3 1_656 yes
C11 H11 O2 0.95 2.39 3.309(3) 162.3 1_656 yes
C12 H12A Br1 0.98 2.93 3.848(9) 157.4 1_666 yes
C12 H12B Br1 0.98 2.80 3.604(10) 139.8 2_666 yes
C12 H12B Cl1 0.98 2.81 3.62(2) 141.5 2_666 yes
O1 H1A Br1 0.83(2) 2.46(3) 3.285(8) 175(4) . yes
O1 H1A Cl1 0.83(2) 2.52(3) 3.340(18) 173(4) . yes
O1 H1B O2 0.82(2) 2.06(2) 2.865(3) 169(4) . yes
O2 H2A Br2 0.84(2) 2.46(2) 3.290(4) 175(4) . yes
O2 H2A Cl2 0.84(2) 2.29(3) 3.116(10) 173(4) . yes
O2 H2B Br1 0.83(2) 2.49(3) 3.303(9) 167(3) 2_565 yes
O2 H2B Cl1 0.83(2) 2.39(3) 3.20(2) 168(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
C1 N1 C5 C4 -1.7(3) . . . .
C1 C2 C3 C4 -2.1(3) . . . .
C1 C2 C3 C9 176.6(2) . . . .
N1 C1 C2 C3 -0.5(4) . . . .
C2 C1 N1 C5 2.5(3) . . . .
C2 C1 N1 C6 -174.7(2) . . . .
C2 C3 C4 C5 2.8(3) . . . .
C2 C3 C9 C8 -2.4(3) . . . .
C2 C3 C9 C10 179.7(2) . . . .
N2 C7 C8 C9 -0.8(3) . . . .
C3 C4 C5 N1 -1.0(3) . . . .
C3 C9 C10 C11 179.3(2) . . . .
C4 C3 C9 C8 176.4(2) . . . .
C4 C3 C9 C10 -1.6(3) . . . .
C6 N1 C5 C4 175.5(2) . . . .
C7 N2 C11 C10 -0.3(3) . . . .
C7 C8 C9 C3 -178.4(2) . . . .
C7 C8 C9 C10 -0.4(3) . . . .
C8 C9 C10 C11 1.3(3) . . . .
C9 C3 C4 C5 -175.9(2) . . . .
C9 C10 C11 N2 -1.0(3) . . . .
C11 N2 C7 C8 1.2(3) . . . .
C12 N2 C7 C8 -176.1(2) . . . .
C12 N2 C11 C10 177.1(2) . . . .

_cod_database_fobs_code 4519472
