#------------------------------------------------------------------------------
#$Date: 2023-11-01 20:43:16 +0200 (Wed, 01 Nov 2023) $
#$Revision: 287200 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/94/4519451.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_4519451
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         '2(Cl), 3(H2 O), C12 H14 N2'
_chemical_formula_sum            'C12 H20 Cl2 N2 O3'
_chemical_formula_weight         311.20
_chemical_name_common            'Paraquat Dichloride Trihydrate'
_chemical_name_systematic
;
1,1'-dimethyl-4,4'-bipyridin-1-ium bis(chloride) trihydrate
;
_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                 108.852(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0643(2)
_cell_length_b                   16.0149(3)
_cell_length_c                   11.2228(2)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.648
_cell_measurement_theta_min      4.347
_cell_volume                     1541.75(5)
_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      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 0.984
_diffrn_measured_fraction_theta_max 0.987
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25232
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.618
_diffrn_reflns_theta_min         4.346
_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    2.548
_exptl_absorpt_correction_T_max  0.4146
_exptl_absorpt_correction_T_min  0.3168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.7641.
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    1.341
_exptl_crystal_description       Block
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method
'crystallzed from DMSO/H2O on a microscope slide'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0259
_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/[σ²(Fo²)+(0.0427P)²+0.2832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3417
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            S05_Pq-Cl2_3H2O_P21_c.cif
_cod_data_source_block           jw22641
_cod_database_code               4519451
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
Cl1 Cl 1.000000 0.500000 0.500000 0.02624(10) Uani 1 2 d S . P . .
Cl2 Cl 1.03369(3) 0.19753(2) 0.49330(2) 0.02624(9) Uani 1 1 d . . . . .
Cl3 Cl 0.500000 0.000000 0.500000 0.02787(10) Uani 1 2 d S . P . .
O1 O 0.40044(10) 0.17607(6) 0.58491(10) 0.0446(2) Uani 1 1 d . . . . .
H1A H 0.306(2) 0.1787(11) 0.5659(17) 0.065(5) Uiso 1 1 d . . . . .
H1B H 0.418(2) 0.1300(12) 0.5590(17) 0.064(5) Uiso 1 1 d . . . . .
O2 O 0.51648(11) 0.30912(5) 0.47485(9) 0.03797(19) Uani 1 1 d . . . . .
H2A H 0.611(2) 0.3178(11) 0.5075(18) 0.068(5) Uiso 1 1 d . . . . .
H2B H 0.4881(19) 0.2742(11) 0.5127(14) 0.049(4) Uiso 1 1 d . . . . .
O3 O 0.83725(11) 0.33975(6) 0.56775(10) 0.0450(2) Uani 1 1 d . . . . .
H3A H 0.869(2) 0.3822(11) 0.5507(16) 0.055(5) Uiso 1 1 d . . . . .
H3B H 0.884(3) 0.3020(12) 0.5517(19) 0.078(6) Uiso 1 1 d . . . . .
N1 N -0.07686(9) 0.38835(5) 0.22661(7) 0.02222(16) Uani 1 1 d . . . . .
N2 N 0.59750(9) 0.61725(5) 0.27135(7) 0.02363(17) Uani 1 1 d . . . . .
C1 C -0.08906(11) 0.46104(6) 0.16443(9) 0.02477(19) Uani 1 1 d D . . . .
H1 H -0.1877(9) 0.4772(8) 0.1147(11) 0.035(3) Uiso 1 1 d D . . . .
C2 C 0.04180(11) 0.50773(6) 0.17360(9) 0.02455(19) Uani 1 1 d D . . . .
H2 H 0.0275(15) 0.5572(6) 0.1284(11) 0.035(3) Uiso 1 1 d D . . . .
C3 C 0.18874(10) 0.47938(5) 0.24762(8) 0.02065(18) Uani 1 1 d . . . . .
C4 C 0.19682(11) 0.40328(6) 0.30923(9) 0.02361(18) Uani 1 1 d D . . . .
H4 H 0.2896(10) 0.3801(7) 0.3595(10) 0.030(3) Uiso 1 1 d D . . . .
C5 C 0.06236(11) 0.35911(6) 0.29770(9) 0.02469(19) Uani 1 1 d D . . . .
H5 H 0.0647(15) 0.3088(5) 0.3393(10) 0.028(3) Uiso 1 1 d D . . . .
C6 C -0.21886(12) 0.34002(7) 0.21773(11) 0.0316(2) Uani 1 1 d D . . . .
H6A H -0.198(2) 0.2861(6) 0.2073(17) 0.069(5) Uiso 1 1 d D . . . .
H6B H -0.235(2) 0.3434(10) 0.2927(12) 0.061(5) Uiso 1 1 d D . . . .
H6C H -0.3001(17) 0.3630(10) 0.1580(14) 0.070(5) Uiso 1 1 d D . . . .
C7 C 0.45691(11) 0.65036(6) 0.21132(9) 0.02511(19) Uani 1 1 d D . . . .
H7 H 0.4542(16) 0.7024(5) 0.1744(11) 0.032(3) Uiso 1 1 d D . . . .
C8 C 0.32270(11) 0.60763(6) 0.20479(9) 0.02406(19) Uani 1 1 d D . . . .
H8 H 0.2287(10) 0.6330(7) 0.1613(11) 0.032(3) Uiso 1 1 d D . . . .
C9 C 0.33160(10) 0.52867(5) 0.25903(8) 0.02076(18) Uani 1 1 d . . . . .
C10 C 0.47945(12) 0.49701(6) 0.32304(10) 0.0263(2) Uani 1 1 d D . . . .
H10 H 0.4939(15) 0.4453(5) 0.3624(11) 0.034(3) Uiso 1 1 d D . . . .
C11 C 0.61042(11) 0.54239(6) 0.32778(9) 0.0270(2) Uani 1 1 d D . . . .
H11 H 0.7110(9) 0.5243(8) 0.3684(12) 0.042(4) Uiso 1 1 d D . . . .
C12 C 0.73970(12) 0.66193(7) 0.26997(11) 0.0322(2) Uani 1 1 d D . . . .
H12A H 0.732(2) 0.7167(6) 0.2840(17) 0.077(6) Uiso 1 1 d D . . . .
H12B H 0.749(2) 0.6562(10) 0.1929(11) 0.061(5) Uiso 1 1 d D . . . .
H12C H 0.8233(16) 0.6417(11) 0.3302(15) 0.079(6) 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'
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
H1A O1 H1B 105.0(18) . .
H2A O2 H2B 110.4(16) . .
H3A O3 H3B 109.5(19) . .
C1 N1 C6 119.69(8) . .
C5 N1 C1 121.03(8) . .
C5 N1 C6 119.28(8) . .
C7 N2 C12 119.52(8) . .
C11 N2 C7 120.85(8) . .
C11 N2 C12 119.56(8) . .
N1 C1 H1 117.2(8) . .
N1 C1 C2 120.48(8) . .
C2 C1 H1 122.3(8) . .
C1 C2 H2 117.3(8) . .
C1 C2 C3 120.00(8) . .
C3 C2 H2 122.7(8) . .
C2 C3 C9 120.99(8) . .
C4 C3 C2 117.82(8) . .
C4 C3 C9 121.19(8) . .
C3 C4 H4 123.1(8) . .
C5 C4 C3 119.99(8) . .
C5 C4 H4 116.9(8) . .
N1 C5 C4 120.68(8) . .
N1 C5 H5 117.8(8) . .
C4 C5 H5 121.5(8) . .
N1 C6 H6A 107.4(12) . .
N1 C6 H6B 107.8(12) . .
N1 C6 H6C 108.8(12) . .
H6A C6 H6B 106.4(15) . .
H6A C6 H6C 116.8(16) . .
H6B C6 H6C 109.2(16) . .
N2 C7 H7 117.5(8) . .
N2 C7 C8 120.62(8) . .
C8 C7 H7 121.8(8) . .
C7 C8 H8 117.2(8) . .
C7 C8 C9 120.13(8) . .
C9 C8 H8 122.7(8) . .
C8 C9 C3 121.21(8) . .
C8 C9 C10 117.70(8) . .
C10 C9 C3 121.09(8) . .
C9 C10 H10 122.2(8) . .
C11 C10 C9 120.02(8) . .
C11 C10 H10 117.7(8) . .
N2 C11 C10 120.64(8) . .
N2 C11 H11 115.7(9) . .
C10 C11 H11 123.6(9) . .
N2 C12 H12A 110.6(13) . .
N2 C12 H12B 108.1(11) . .
N2 C12 H12C 110.2(13) . .
H12A C12 H12B 107.7(16) . .
H12A C12 H12C 108.4(16) . .
H12B C12 H12C 111.7(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1A 0.81(2) .
O1 H1B 0.83(2) .
O2 H2A 0.83(2) .
O2 H2B 0.794(17) .
O3 H3A 0.787(19) .
O3 H3B 0.79(2) .
N1 C1 1.3433(12) .
N1 C5 1.3408(12) .
N1 C6 1.4775(12) .
N2 C7 1.3432(12) .
N2 C11 1.3432(13) .
N2 C12 1.4787(12) .
C1 H1 0.925(6) .
C1 C2 1.3777(13) .
C2 H2 0.927(6) .
C2 C3 1.3983(12) .
C3 C4 1.3915(12) .
C3 C9 1.4863(13) .
C4 H4 0.926(6) .
C4 C5 1.3786(13) .
C5 H5 0.928(6) .
C6 H6A 0.900(9) .
C6 H6B 0.901(9) .
C6 H6C 0.899(9) .
C7 H7 0.927(6) .
C7 C8 1.3769(13) .
C8 H8 0.928(6) .
C8 C9 1.3944(12) .
C9 C10 1.3954(12) .
C10 H10 0.927(6) .
C10 C11 1.3782(13) .
C11 H11 0.924(7) .
C12 H12A 0.899(9) .
C12 H12B 0.899(9) .
C12 H12C 0.897(9) .
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
O1 H1A Cl2 0.81(2) 2.35(2) 3.1651(9) 173.4(18) 1_455 yes
O2 H2A O3 0.83(2) 1.97(2) 2.7969(13) 174.1(18) . yes
O2 H2B O1 0.794(17) 2.043(18) 2.8305(14) 171.6(15) . yes
O3 H3A Cl1 0.787(19) 2.392(19) 3.1726(10) 171.7(17) . yes
O3 H3B Cl2 0.79(2) 2.37(2) 3.1650(10) 175(2) . yes
C2 H2 Cl2 0.927(6) 2.595(7) 3.5196(9) 175.2(11) 2_655 yes
C4 H4 O2 0.926(6) 2.340(7) 3.2625(12) 174.2(11) . yes
C5 H5 Cl2 0.928(6) 2.560(7) 3.4571(9) 162.6(11) 1_455 yes
C6 H6A O3 0.900(9) 2.635(12) 3.4545(15) 151.9(15) 4_465 yes
C7 H7 O2 0.927(6) 2.467(8) 3.3488(13) 158.9(11) 2_655 yes
C8 H8 Cl2 0.928(6) 2.659(7) 3.5791(9) 171.7(11) 2_655 yes
C10 H10 O2 0.927(6) 2.495(7) 3.4206(13) 175.7(11) . 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 0.27(14) . . . .
N2 C7 C8 C9 -1.00(14) . . . .
C1 N1 C5 C4 0.31(14) . . . .
C1 C2 C3 C4 0.57(14) . . . .
C1 C2 C3 C9 -179.97(9) . . . .
C2 C3 C4 C5 -0.98(13) . . . .
C2 C3 C9 C8 5.22(14) . . . .
C2 C3 C9 C10 -173.93(8) . . . .
C3 C4 C5 N1 0.56(14) . . . .
C3 C9 C10 C11 177.25(9) . . . .
C4 C3 C9 C8 -175.34(8) . . . .
C4 C3 C9 C10 5.52(14) . . . .
C5 N1 C1 C2 -0.73(14) . . . .
C6 N1 C1 C2 178.73(9) . . . .
C6 N1 C5 C4 -179.15(9) . . . .
C7 N2 C11 C10 1.39(14) . . . .
C7 C8 C9 C3 -176.80(9) . . . .
C7 C8 C9 C10 2.38(13) . . . .
C8 C9 C10 C11 -1.93(14) . . . .
C9 C3 C4 C5 179.56(9) . . . .
C9 C10 C11 N2 0.09(15) . . . .
C11 N2 C7 C8 -0.93(14) . . . .
C12 N2 C7 C8 176.07(9) . . . .
C12 N2 C11 C10 -175.62(9) . . . .

_cod_database_fobs_code 4519451
