#------------------------------------------------------------------------------
#$Date: 2017-04-05 12:33:59 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195028 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/78/7227824.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_7227824
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_formula_moiety         'C8 H6 Cl2 Li1 N2 O5'
_chemical_formula_sum            'C8 H6 Cl2 Li N2 O5'
_chemical_formula_weight         287.99
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2013-09-03T11:08:58-00:00
_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                94.183(12)
_cell_angle_beta                 106.050(13)
_cell_angle_gamma                110.302(14)
_cell_formula_units_Z            2
_cell_length_a                   7.9750(12)
_cell_length_b                   8.0294(13)
_cell_length_c                   10.4361(14)
_cell_measurement_reflns_used    2022
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4118
_cell_measurement_theta_min      4.4844
_cell_volume                     591.66(17)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'CCD, ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4289
_diffrn_reflns_theta_full        75.6
_diffrn_reflns_theta_max         75.6
_diffrn_reflns_theta_min         4.49
_exptl_absorpt_coefficient_mu    5.096
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.33684
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.444
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2400
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1160P)²+0.0627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1705
_reflns_number_gt                2101
_reflns_number_total             2400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00261k2.cif
_cod_data_source_block           liddq-rt
_cod_depositor_comments
'Adding full bibliography for 7227819--7227824.cif.'
_cod_original_cell_volume        591.66(15)
_cod_database_code               7227824
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_atom_site_refinement_flags
Li1 Li 0.6564(8) 0.8239(7) 0.5146(5) 0.0552(11) Uani 1 d .
Cl1 Cl 0.44782(10) 0.65407(9) 0.81741(8) 0.0581(3) Uani 1 d .
Cl2 Cl 0.53876(10) 0.79234(9) 1.12663(7) 0.0542(3) Uani 1 d .
O1 O 0.8706(3) 1.1324(3) 1.23548(18) 0.0482(4) Uani 1 d .
O2 O 0.7138(3) 0.8894(3) 0.70209(19) 0.0546(5) Uani 1 d .
N1 N 1.1879(4) 1.4932(3) 1.1592(2) 0.0533(6) Uani 1 d .
N2 N 1.0663(4) 1.2951(4) 0.7396(3) 0.0572(6) Uani 1 d .
C1 C 0.8343(4) 1.0772(3) 1.1127(2) 0.0394(5) Uani 1 d .
C2 C 0.9407(3) 1.1793(3) 1.0321(2) 0.0380(5) Uani 1 d .
C3 C 0.9007(3) 1.1165(3) 0.8949(2) 0.0386(5) Uani 1 d .
C4 C 0.7501(4) 0.9461(3) 0.8235(2) 0.0408(5) Uani 1 d .
C5 C 0.6369(3) 0.8470(3) 0.9037(3) 0.0424(5) Uani 1 d .
C6 C 0.6771(3) 0.9079(3) 1.0380(2) 0.0415(5) Uani 1 d .
C7 C 1.0806(4) 1.3542(3) 1.1007(2) 0.0407(5) Uani 1 d .
C8 C 0.9970(4) 1.2201(3) 0.8117(2) 0.0419(5) Uani 1 d .
O3 O 0.3866(4) 0.6664(3) 0.4443(2) 0.0623(6) Uani 1 d D
H3A H 0.350(7) 0.557(4) 0.477(4) 0.088(14) Uiso 1 d D
H3B H 0.317(6) 0.621(6) 0.352(2) 0.090(14) Uiso 1 d D
O4 O 0.6993(4) 1.0385(4) 0.4390(2) 0.0710(7) Uani 1 d D
H4A H 0.732(7) 1.059(6) 0.361(3) 0.079(13) Uiso 1 d D
H4B H 0.653(8) 1.124(6) 0.464(5) 0.103(17) Uiso 1 d D
O5 O 0.8201(3) 0.6882(3) 0.5071(2) 0.0586(5) Uani 1 d D
H5A H 0.926(5) 0.750(6) 0.585(3) 0.089(14) Uiso 1 d D
H5B H 0.865(6) 0.696(6) 0.434(3) 0.090(14) Uiso 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 0.0181 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'
Li Li 0.0008 0.0003 '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
O2 Li1 O4 108.2(3)
O2 Li1 O3 106.2(3)
O4 Li1 O3 109.9(3)
O2 Li1 O5 101.4(3)
O4 Li1 O5 118.1(3)
O3 Li1 O5 112.0(3)
C4 O2 Li1 174.6(3)
O1 C1 C2 122.3(2)
O1 C1 C6 122.4(2)
C2 C1 C6 115.3(2)
C3 C2 C7 122.2(2)
C3 C2 C1 122.1(2)
C7 C2 C1 115.6(2)
C2 C3 C8 122.9(2)
C2 C3 C4 122.1(2)
C8 C3 C4 114.9(2)
O2 C4 C3 122.5(2)
O2 C4 C5 121.8(2)
C3 C4 C5 115.7(2)
C6 C5 C4 122.1(2)
C6 C5 Cl1 121.7(2)
C4 C5 Cl1 116.15(18)
C5 C6 C1 122.6(2)
C5 C6 Cl2 120.8(2)
C1 C6 Cl2 116.58(18)
N1 C7 C2 177.1(2)
N2 C8 C3 176.2(3)
Li1 O3 H3A 117(3)
Li1 O3 H3B 125(3)
H3A O3 H3B 99(3)
Li1 O4 H4A 128(3)
Li1 O4 H4B 120(3)
H4A O4 H4B 110(3)
Li1 O5 H5A 102(3)
Li1 O5 H5B 115(3)
H5A O5 H5B 106(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Li1 O2 1.871(5)
Li1 O4 1.909(6)
Li1 O3 1.967(6)
Li1 O5 1.982(6)
Cl1 C5 1.706(3)
Cl2 C6 1.707(2)
O1 C1 1.243(3)
O2 C4 1.232(3)
N1 C7 1.140(4)
N2 C8 1.139(4)
C1 C2 1.454(3)
C1 C6 1.466(4)
C2 C3 1.391(3)
C2 C7 1.433(3)
C3 C8 1.438(3)
C3 C4 1.444(4)
C4 C5 1.471(4)
C5 C6 1.360(4)
O3 H3A 0.948(19)
O3 H3B 0.936(19)
O4 H4A 0.931(19)
O4 H4B 0.933(19)
O5 H5A 0.946(19)
O5 H5B 0.927(19)
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
O4 Li1 O2 C4 19(3)
O3 Li1 O2 C4 -99(3)
O5 Li1 O2 C4 144(3)
O1 C1 C2 C3 179.5(2)
C6 C1 C2 C3 -2.6(3)
O1 C1 C2 C7 -4.7(3)
C6 C1 C2 C7 173.3(2)
C7 C2 C3 C8 0.7(3)
C1 C2 C3 C8 176.3(2)
C7 C2 C3 C4 -175.2(2)
C1 C2 C3 C4 0.3(3)
Li1 O2 C4 C3 -55(3)
Li1 O2 C4 C5 122(3)
C2 C3 C4 O2 -179.9(2)
C8 C3 C4 O2 3.8(3)
C2 C3 C4 C5 2.4(3)
C8 C3 C4 C5 -173.8(2)
O2 C4 C5 C6 179.4(2)
C3 C4 C5 C6 -2.9(3)
O2 C4 C5 Cl1 -2.4(3)
C3 C4 C5 Cl1 175.29(16)
C4 C5 C6 C1 0.7(4)
Cl1 C5 C6 C1 -177.41(17)
C4 C5 C6 Cl2 178.19(17)
Cl1 C5 C6 Cl2 0.1(3)
O1 C1 C6 C5 -180.0(2)
C2 C1 C6 C5 2.1(3)
O1 C1 C6 Cl2 2.4(3)
C2 C1 C6 Cl2 -175.56(16)
C3 C2 C7 N1 156(5)
C1 C2 C7 N1 -20(5)
C2 C3 C8 N2 -172(4)
C4 C3 C8 N2 4(4)
