#------------------------------------------------------------------------------
#$Date: 2024-12-10 10:45:32 +0200 (Tue, 10 Dec 2024) $
#$Revision: 296814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/78/7227821.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_7227821
loop_
_publ_author_name
'Molčanov, Krešimir'
'Kojić-Prodić, Biserka'
_publ_section_title
;
 Spin pairing, electrostatic and dipolar interactions influence stacking
 of radical anions in alkali salts of
 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (DDQ)
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1801
_journal_paper_doi               10.1039/C7CE00261K
_journal_volume                  19
_journal_year                    2017
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H10 Cl2 Cs N2 O4'
_chemical_formula_sum            'C12 H10 Cl2 Cs N2 O4'
_chemical_formula_weight         450.03
_chemical_properties_physical    ', Air-sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-03-16T15:23:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-02-03 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                109.248(4)
_cell_angle_beta                 92.148(4)
_cell_angle_gamma                90.445(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1080(3)
_cell_length_b                   10.6399(5)
_cell_length_c                   12.5460(7)
_cell_measurement_reflns_used    3446
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7016
_cell_measurement_theta_min      3.732
_cell_measurement_wavelength     1.54179
_cell_volume                     769.05(7)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0527662
_diffrn_orient_matrix_UB_12      -0.0292595
_diffrn_orient_matrix_UB_13      0.1104465
_diffrn_orient_matrix_UB_21      -0.1915612
_diffrn_orient_matrix_UB_22      -0.1022445
_diffrn_orient_matrix_UB_23      -0.0280324
_diffrn_orient_matrix_UB_31      0.1557332
_diffrn_orient_matrix_UB_32      -0.110552
_diffrn_orient_matrix_UB_33      -0.0629481
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6498
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         75.882
_diffrn_reflns_theta_min         3.735
_exptl_absorpt_coefficient_mu    22.138
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.35952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             434
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.032
_refine_diff_density_min         -0.82
_refine_diff_density_rms         0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0681P)²+1.0729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                2913
_reflns_number_total             3129
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce00261k2.cif
_cod_data_source_block           csddq-mecoet-100k
_cod_depositor_comments
'Adding full bibliography for 7227819--7227824.cif.'
_cod_database_code               7227821
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_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_calc_flag
Cs1 Cs 0.25140(5) 0.53096(3) 0.87651(2) 0.02319(13) Uani 1 d
Cl1 Cl 0.2473(2) 1.33439(12) 1.22999(11) 0.0273(3) Uani 1 d
Cl2 Cl 0.2754(2) 1.03940(13) 1.24179(10) 0.0255(3) Uani 1 d
O1 O 0.3009(6) 0.8375(4) 1.0169(3) 0.0219(7) Uani 1 d
O2 O 0.2096(7) 1.3376(4) 0.9999(3) 0.0259(8) Uani 1 d
C1 C 0.2803(8) 0.9526(5) 1.0136(4) 0.0180(9) Uani 1 d
C2 C 0.2590(8) 0.9789(5) 0.9070(4) 0.0190(9) Uani 1 d
C3 C 0.2415(8) 1.1072(5) 0.9019(4) 0.0194(9) Uani 1 d
C4 C 0.2357(8) 1.2240(5) 1.0030(4) 0.0202(10) Uani 1 d
C5 C 0.2544(8) 1.1957(5) 1.1103(4) 0.0208(10) Uani 1 d
C6 C 0.2709(8) 1.0711(5) 1.1153(4) 0.0201(9) Uani 1 d
C7 C 0.2505(8) 0.8601(5) 0.8040(5) 0.0236(11) Uani 1 d
C8 C 0.2222(9) 1.1300(5) 0.7925(5) 0.0246(11) Uani 1 d
N1 N 0.2475(9) 0.7710(6) 0.7317(5) 0.0319(11) Uani 1 d
N2 N 0.2162(10) 1.1450(6) 0.7111(5) 0.0381(12) Uani 1 d
O3 O 0.3312(7) 0.6513(4) 1.1408(3) 0.0297(8) Uani 1 d
H3B H 0.262(15) 0.664(9) 1.209(5) 0.06(3) Uiso 1 d
H3A H 0.310(15) 0.730(6) 1.122(7) 0.06(3) Uiso 1 d
O4 O -0.0876(8) 0.3700(4) 0.6761(4) 0.0340(9) Uani 1 d
C9 C -0.0748(10) 0.2831(6) 0.5853(5) 0.0284(11) Uani 1 d
C10 C -0.2369(12) 0.1678(7) 0.5472(6) 0.0421(15) Uani 1 d
H10A H -0.3409 0.1769 0.6046 0.063 Uiso 1 calc
H10B H -0.1606 0.0859 0.5341 0.063 Uiso 1 calc
H10C H -0.3125 0.1673 0.4785 0.063 Uiso 1 calc
C11 C 0.1070(11) 0.2827(7) 0.5071(5) 0.0352(13) Uani 1 d
H11A H 0.1814 0.1985 0.4899 0.042 Uiso 1 calc
H11B H 0.0423 0.2875 0.4368 0.042 Uiso 1 calc
C12 C 0.2751(13) 0.3940(8) 0.5522(6) 0.0441(16) Uani 1 d
H12A H 0.3807 0.388 0.4961 0.066 Uiso 1 calc
H12B H 0.3478 0.3869 0.6191 0.066 Uiso 1 calc
H12C H 0.2037 0.4781 0.5702 0.066 Uiso 1 calc
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.7457 7.9052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
O2 Cs1 O3 64.81(11) 1_545 .
O2 Cs1 O1 118.78(10) 1_545 .
O3 Cs1 O1 54.61(10) . .
O2 Cs1 O3 66.77(11) 1_545 2_667
O3 Cs1 O3 90.46(10) . 2_667
O1 Cs1 O3 118.49(11) . 2_667
O2 Cs1 O4 93.70(12) 1_545 .
O3 Cs1 O4 145.03(11) . .
O1 Cs1 O4 131.61(11) . .
O3 Cs1 O4 106.60(11) 2_667 .
O2 Cs1 O2 85.87(10) 1_545 2_577
O3 Cs1 O2 69.41(11) . 2_577
O1 Cs1 O2 66.67(10) . 2_577
O3 Cs1 O2 151.37(10) 2_667 2_577
O4 Cs1 O2 82.44(11) . 2_577
O2 Cs1 N1 174.52(11) 1_545 .
O3 Cs1 N1 114.90(12) . .
O1 Cs1 N1 60.37(11) . .
O3 Cs1 N1 118.62(12) 2_667 .
O4 Cs1 N1 83.84(12) . .
O2 Cs1 N1 88.95(11) 2_577 .
O2 Cs1 O2 95.83(10) 1_545 2_677
O3 Cs1 O2 59.28(10) . 2_677
O1 Cs1 O2 61.59(9) . 2_677
O3 Cs1 O2 56.96(10) 2_667 2_677
O4 Cs1 O2 154.85(10) . 2_677
O2 Cs1 O2 121.40(12) 2_577 2_677
N1 Cs1 O2 88.39(11) . 2_677
O2 Cs1 Cl1 121.03(8) 1_545 2_577
O3 Cs1 Cl1 113.12(8) . 2_577
O1 Cs1 Cl1 78.88(7) . 2_577
O3 Cs1 Cl1 156.39(8) 2_667 2_577
O4 Cs1 Cl1 53.06(8) . 2_577
O2 Cs1 Cl1 47.66(7) 2_577 2_577
N1 Cs1 Cl1 53.68(9) . 2_577
O2 Cs1 Cl1 136.03(6) 2_677 2_577
O2 Cs1 Cl1 131.69(8) 1_545 2_677
O3 Cs1 Cl1 101.91(9) . 2_677
O1 Cs1 Cl1 72.82(7) . 2_677
O3 Cs1 Cl1 67.20(8) 2_667 2_677
O4 Cs1 Cl1 112.76(8) . 2_677
O2 Cs1 Cl1 135.20(7) 2_577 2_677
N1 Cs1 Cl1 53.74(9) . 2_677
O2 Cs1 Cl1 45.48(6) 2_677 2_677
Cl1 Cs1 Cl1 107.04(3) 2_577 2_677
O2 Cs1 C12 118.20(15) 1_545 .
O3 Cs1 C12 168.84(14) . .
O1 Cs1 C12 122.94(14) . .
O3 Cs1 C12 81.59(15) 2_667 .
O4 Cs1 C12 45.82(14) . .
O2 Cs1 C12 120.74(14) 2_577 .
N1 Cs1 C12 63.24(15) . .
O2 Cs1 C12 109.62(13) 2_677 .
Cl1 Cs1 C12 75.22(13) 2_577 .
Cl1 Cs1 C12 67.81(11) 2_677 .
O2 Cs1 C7 162.16(11) 1_545 .
O3 Cs1 C7 99.24(12) . .
O1 Cs1 C7 44.64(11) . .
O3 Cs1 C7 123.88(11) 2_667 .
O4 Cs1 C7 96.09(12) . .
O2 Cs1 C7 80.70(10) 2_577 .
N1 Cs1 C7 15.81(13) . .
O2 Cs1 C7 81.42(10) 2_677 .
Cl1 Cs1 C7 55.98(8) 2_577 .
Cl1 Cs1 C7 56.70(8) 2_677 .
C12 Cs1 C7 79.03(15) . .
C5 Cl1 Cs1 93.39(18) . 2_577
C5 Cl1 Cs1 87.47(17) . 2_677
Cs1 Cl1 Cs1 107.04(3) 2_577 2_677
C1 O1 Cs1 145.0(3) . .
C4 O2 Cs1 149.0(3) . 1_565
C4 O2 Cs1 111.4(3) . 2_577
Cs1 O2 Cs1 94.13(10) 1_565 2_577
C4 O2 Cs1 96.3(3) . 2_677
Cs1 O2 Cs1 84.17(9) 1_565 2_677
Cs1 O2 Cs1 121.40(11) 2_577 2_677
O1 C1 C2 121.8(5) . .
O1 C1 C6 123.3(5) . .
C2 C1 C6 114.9(4) . .
C3 C2 C1 122.4(4) . .
C3 C2 C7 121.9(4) . .
C1 C2 C7 115.6(4) . .
C2 C3 C4 122.2(5) . .
C2 C3 C8 120.9(4) . .
C4 C3 C8 116.9(5) . .
O2 C4 C3 123.0(5) . .
O2 C4 C5 122.2(5) . .
C3 C4 C5 114.8(5) . .
C6 C5 C4 123.0(5) . .
C6 C5 Cl1 122.3(4) . .
C4 C5 Cl1 114.7(4) . .
C5 C6 C1 122.6(5) . .
C5 C6 Cl2 122.2(4) . .
C1 C6 Cl2 115.2(4) . .
N1 C7 C2 177.2(6) . .
N1 C7 Cs1 65.6(4) . .
C2 C7 Cs1 111.8(3) . .
N2 C8 C3 177.2(6) . .
C7 N1 Cs1 98.6(4) . .
Cs1 O3 Cs1 89.54(10) . 2_667
Cs1 O3 H3B 142(6) . .
Cs1 O3 H3B 111(5) 2_667 .
Cs1 O3 H3A 79(6) . .
Cs1 O3 H3A 131(6) 2_667 .
H3B O3 H3A 106(4) . .
C9 O4 Cs1 135.7(4) . .
O4 C9 C10 121.2(6) . .
O4 C9 C11 121.9(6) . .
C10 C9 C11 116.9(5) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C12 C11 C9 115.2(5) . .
C12 C11 H11A 108.5 . .
C9 C11 H11A 108.5 . .
C12 C11 H11B 108.5 . .
C9 C11 H11B 108.5 . .
H11A C11 H11B 107.5 . .
C11 C12 Cs1 108.6(4) . .
C11 C12 H12A 109.5 . .
Cs1 C12 H12A 137.8 . .
C11 C12 H12B 109.5 . .
Cs1 C12 H12B 39.1 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
Cs1 C12 H12C 73.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cs1 O2 2.969(4) 1_545
Cs1 O3 3.153(4) .
Cs1 O1 3.160(4) .
Cs1 O3 3.186(4) 2_667
Cs1 O4 3.203(5) .
Cs1 O2 3.353(4) 2_577
Cs1 N1 3.589(5) .
Cs1 O2 3.649(4) 2_677
Cs1 Cl1 3.7607(14) 2_577
Cs1 Cl1 3.8357(14) 2_677
Cs1 C12 3.852(7) .
Cs1 C7 3.897(5) .
Cs1 H3A 3.12(9) .
Cl1 C5 1.725(5) .
Cl1 Cs1 3.7607(14) 2_577
Cl1 Cs1 3.8357(13) 2_677
Cl2 C6 1.727(5) .
O1 C1 1.246(6) .
O2 C4 1.234(7) .
O2 Cs1 2.969(4) 1_565
O2 Cs1 3.353(4) 2_577
O2 Cs1 3.649(4) 2_677
C1 C2 1.455(7) .
C1 C6 1.473(7) .
C2 C3 1.392(7) .
C2 C7 1.480(7) .
C3 C4 1.456(7) .
C3 C8 1.471(8) .
C4 C5 1.474(7) .
C5 C6 1.352(7) .
C7 N1 1.074(8) .
C8 N2 1.084(9) .
O3 Cs1 3.185(4) 2_667
O3 H3B 0.94(7) .
O3 H3A 0.95(7) .
O4 C9 1.214(8) .
C9 C10 1.507(9) .
C9 C11 1.508(8) .
C10 H10A 0.96 .
C10 H10B 0.96 .
C10 H10C 0.96 .
C11 C12 1.508(10) .
C11 H11A 0.97 .
C11 H11B 0.97 .
C12 H12A 0.96 .
C12 H12B 0.96 .
C12 H12C 0.96 .
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
Cs1 O1 C1 C2 -15.7(9) .
Cs1 O1 C1 C6 162.9(4) .
O1 C1 C2 C3 -178.3(5) .
C6 C1 C2 C3 2.9(7) .
O1 C1 C2 C7 3.4(7) .
C6 C1 C2 C7 -175.4(4) .
C1 C2 C3 C4 -2.2(8) .
C7 C2 C3 C4 176.0(4) .
C1 C2 C3 C8 179.4(5) .
C7 C2 C3 C8 -2.4(8) .
Cs1 O2 C4 C3 -25.8(10) 1_565
Cs1 O2 C4 C3 117.8(4) 2_577
Cs1 O2 C4 C3 -114.9(4) 2_677
Cs1 O2 C4 C5 156.7(5) 1_565
Cs1 O2 C4 C5 -59.7(5) 2_577
Cs1 O2 C4 C5 67.6(5) 2_677
C2 C3 C4 O2 -176.4(5) .
C8 C3 C4 O2 2.1(7) .
C2 C3 C4 C5 1.2(7) .
C8 C3 C4 C5 179.7(5) .
O2 C4 C5 C6 176.2(5) .
C3 C4 C5 C6 -1.4(7) .
O2 C4 C5 Cl1 -2.3(7) .
C3 C4 C5 Cl1 -180.0(3) .
Cs1 Cl1 C5 C6 -130.1(4) 2_577
Cs1 Cl1 C5 C6 123.0(4) 2_677
Cs1 Cl1 C5 C4 48.5(4) 2_577
Cs1 Cl1 C5 C4 -58.4(4) 2_677
C4 C5 C6 C1 2.4(8) .
Cl1 C5 C6 C1 -179.1(4) .
C4 C5 C6 Cl2 -175.8(4) .
Cl1 C5 C6 Cl2 2.6(7) .
O1 C1 C6 C5 178.2(5) .
C2 C1 C6 C5 -3.0(7) .
O1 C1 C6 Cl2 -3.4(7) .
C2 C1 C6 Cl2 175.4(4) .
C3 C2 C7 Cs1 -174.4(4) .
C1 C2 C7 Cs1 3.8(5) .
Cs1 O4 C9 C10 137.1(5) .
Cs1 O4 C9 C11 -40.9(9) .
O4 C9 C11 C12 2.5(9) .
C10 C9 C11 C12 -175.6(6) .
C9 C11 C12 Cs1 20.8(7) .
