#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/57/2105741.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_2105741
loop_
_publ_author_name
'Molčanov, Krešimir'
'Babić, Darko'
'Kojić-Prodić, Biserka'
'Stare, Jernej'
'Maltar-Strmečki, Nadica'
'Androš, Lidija'
_publ_section_title
;
 Spin-coupling in dimers of 2,3-dicyano-5,6-dichlorosemiquinone radical
 anions in the crystalline state
;
_journal_coeditor_code           BI5007
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              181
_journal_page_last               190
_journal_paper_doi               10.1107/S2052520613027170
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C11 H10 Cl2 Li1 N2 O5'
_chemical_formula_sum            'C11 H10 Cl2 Li N2 O5'
_chemical_formula_weight         328.06
_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_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                110.773(5)
_cell_angle_beta                 99.693(5)
_cell_angle_gamma                100.335(5)
_cell_formula_units_Z            2
_cell_length_a                   6.667(5)
_cell_length_b                   10.495(5)
_cell_length_c                   11.977(5)
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.7220
_cell_measurement_theta_min      4.0763
_cell_volume                     745.9(7)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       'CrysAlisPro (Agilent, 2012)'
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012) & Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) & PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5368
_diffrn_reflns_theta_full        76.92
_diffrn_reflns_theta_max         76.92
_diffrn_reflns_theta_min         4.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.114
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Agilent, 2012)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.877
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_gt           0.1
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1271P)²+4.0961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3103
_reflns_number_gt                2204
_reflns_number_total             2981
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi5007sup1.cif
_cod_data_source_block           LiDDQx2H2OxMe2O
_cod_database_code               2105741
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Li Li1 0.3160(18) 0.5055(10) 0.4330(10) 0.036(2) Uani d . 1 . .
O O1 0.2407(8) 0.6714(5) 0.4572(6) 0.0506(14) Uani d . 1 . .
O O2 0.1574(7) 1.1817(4) 0.4743(4) 0.0354(11) Uani d . 1 A .
C C1 0.2200(10) 0.7887(6) 0.4601(7) 0.0383(16) Uani d . 1 A .
C C2 0.3097(9) 0.9166(7) 0.5719(6) 0.0358(15) Uani d D 1 . .
C C3 0.2919(9) 1.0460(6) 0.5758(6) 0.0337(14) Uani d D 1 A .
C C4 0.1828(9) 1.0649(6) 0.4698(6) 0.0311(13) Uani d . 1 . .
C C5 0.1042(10) 0.9372(6) 0.3558(6) 0.0354(14) Uani d D 1 A .
C C6 0.1266(9) 0.8076(6) 0.3521(6) 0.0360(14) Uani d D 1 . .
Cl Cl1B 0.4113(9) 1.2027(4) 0.7133(3) 0.0369(9) Uani d PDU 0.658(6) A 1
Cl Cl2B 0.4507(9) 0.9014(7) 0.7054(4) 0.0453(10) Uani d PDU 0.658(6) A 1
N N2B -0.0562(19) 0.9755(12) 0.1665(11) 0.046(2) Uani d PDU 0.658(6) A 1
N N1B -0.006(2) 0.5903(15) 0.1503(13) 0.061(3) Uani d PDU 0.658(6) A 1
C C7B 0.039(5) 0.678(2) 0.2418(17) 0.047(4) Uani d PDU 0.658(6) A 1
C C8B 0.009(4) 0.959(3) 0.2501(16) 0.044(3) Uani d PDU 0.658(6) A 1
Cl Cl1A 0.0042(15) 0.9544(10) 0.2118(7) 0.0422(19) Uani d PDU 0.342(6) A 2
Cl Cl2A 0.0395(18) 0.6581(11) 0.2036(8) 0.046(2) Uani d PDU 0.342(6) A 2
C C7A 0.419(9) 0.890(7) 0.674(4) 0.048(3) Uani d PDU 0.342(6) A 2
C C8A 0.395(8) 1.174(3) 0.682(3) 0.036(3) Uani d PDU 0.342(6) A 2
N N1A 0.510(3) 0.879(2) 0.7566(16) 0.049(2) Uani d PDU 0.342(6) A 2
N N2A 0.444(3) 1.278(2) 0.7637(18) 0.043(3) Uani d PDU 0.342(6) A 2
O O4 0.1132(8) 0.3356(5) 0.3135(5) 0.0438(12) Uani d D 1 . .
H H4A -0.012(6) 0.365(6) 0.302(6) 0.03 Uiso d D 1 . .
H H4B 0.072(9) 0.252(4) 0.328(6) 0.03 Uiso d D 1 . .
O O5 0.3900(7) 0.4638(4) 0.5826(4) 0.0327(10) Uani d D 1 . .
H H5A 0.325(10) 0.370(3) 0.569(5) 0.03 Uiso d D 1 . .
H H5B 0.395(10) 0.519(5) 0.665(3) 0.03 Uiso d D 1 . .
O O3 0.7187(8) 0.3656(5) 0.2188(4) 0.0405(11) Uani d . 1 . .
C C9 0.6198(13) 0.3127(7) 0.1136(7) 0.0449(17) Uani d . 1 . .
C C10 0.6981(19) 0.2124(12) 0.0172(8) 0.082(3) Uani d . 1 . .
H H10A 0.8297 0.2021 0.0551 0.123 Uiso calc R 1 . .
H H10B 0.7181 0.2487 -0.0440 0.123 Uiso calc R 1 . .
H H10C 0.5967 0.1222 -0.0200 0.123 Uiso calc R 1 . .
C C11 0.4134(19) 0.3420(13) 0.0739(10) 0.089(4) Uani d . 1 . .
H H11A 0.3818 0.4067 0.1443 0.133 Uiso calc R 1 . .
H H11B 0.3041 0.2554 0.0381 0.133 Uiso calc R 1 . .
H H11C 0.4224 0.3826 0.014 0.133 Uiso calc R 1 . .
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'
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'
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 Li1 O4 . . 116.2(6)
O1 Li1 O5 . 2_666 107.4(5)
O4 Li1 O5 . 2_666 117.7(5)
O1 Li1 O5 . . 116.2(6)
O4 Li1 O5 . . 104.5(5)
O5 Li1 O5 2_666 . 92.8(5)
O1 Li1 Li1 . 2_666 122.5(7)
O4 Li1 Li1 . 2_666 121.2(6)
O5 Li1 Li1 2_666 2_666 46.6(4)
O5 Li1 Li1 . 2_666 46.2(3)
O1 Li1 H4A . . 93.8(11)
O4 Li1 H4A . . 23.1(10)
O5 Li1 H4A 2_666 . 135.2(15)
O5 Li1 H4A . . 112.8(15)
Li1 Li1 H4A 2_666 . 142.6(11)
C1 O1 Li1 . . 166.9(5)
O1 C1 C6 . . 122.4(7)
O1 C1 C2 . . 121.3(7)
C6 C1 C2 . . 116.0(5)
C3 C2 C7A . . 125(3)
C3 C2 C1 . . 121.9(6)
C7A C2 C1 . . 113(3)
C3 C2 Cl2B . . 120.1(6)
C1 C2 Cl2B . . 118.0(4)
C2 C3 C8A . . 122(2)
C2 C3 C4 . . 122.5(6)
C8A C3 C4 . . 115(2)
C2 C3 Cl1B . . 120.9(6)
C4 C3 Cl1B . . 116.6(4)
O2 C4 C3 . . 122.8(6)
O2 C4 C5 . . 121.8(6)
C3 C4 C5 . . 115.3(5)
C6 C5 C8B . . 123.4(12)
C6 C5 C4 . . 121.7(6)
C8B C5 C4 . . 114.8(11)
C6 C5 Cl1A . . 119.1(6)
C4 C5 Cl1A . . 118.7(5)
C5 C6 C1 . . 122.2(6)
C5 C6 C7B . . 122.8(14)
C1 C6 C7B . . 114.7(13)
C5 C6 Cl2A . . 118.1(7)
C1 C6 Cl2A . . 119.6(6)
N2B C8B C5 . . 177(2)
N1B C7B C6 . . 168(2)
N2A C8A C3 . . 169(5)
N1A C7A C2 . . 176(6)
O3 C9 C11 . . 121.4(7)
O3 C9 C10 . . 120.4(8)
C11 C9 C10 . . 118.1(8)
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
C9 C11 H11A . . 109.5
C9 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C9 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
Li1 O4 H4A . . 103(4)
Li1 O4 H4B . . 124(4)
H4A O4 H4B . . 104(4)
Li1 O5 Li1 2_666 . 87.2(5)
Li1 O5 H5A 2_666 . 114(4)
Li1 O5 H5A . . 112(4)
Li1 O5 H5B 2_666 . 107(4)
Li1 O5 H5B . . 129(4)
H5A O5 H5B . . 106(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Li1 O1 . 1.837(10)
Li1 O4 . 1.931(12)
Li1 O5 2_666 1.980(12)
Li1 O5 . 1.994(11)
Li1 Li1 2_666 2.74(2)
Li1 H4A . 2.34(5)
O1 C1 . 1.251(7)
O2 C4 . 1.252(6)
C1 C6 . 1.435(10)
C1 C2 . 1.456(10)
C2 C3 . 1.369(8)
C2 C7A . 1.453(16)
C2 Cl2B . 1.788(7)
C3 C8A . 1.435(18)
C3 C4 . 1.449(9)
C3 Cl1B . 1.793(7)
C4 C5 . 1.464(9)
C5 C6 . 1.381(7)
C5 C8B . 1.429(15)
C5 Cl1A . 1.824(10)
C6 C7B . 1.457(16)
C6 Cl2A . 1.819(10)
N2B C8B . 1.108(15)
N1B C7B . 1.100(16)
C8A N2A . 1.125(17)
C7A N1A . 1.128(16)
O3 C9 . 1.194(9)
C9 C11 . 1.499(12)
C9 C10 . 1.500(10)
C10 H10A . 0.96
C10 H10B . 0.96
C10 H10C . 0.96
C11 H11A . 0.96
C11 H11B . 0.96
C11 H11C . 0.96
O4 H4A . 0.94(2)
O4 H4B . 0.95(2)
O5 Li1 2_666 1.980(12)
O5 H5A . 0.95(2)
O5 H5B . 0.95(2)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O4 Li1 O1 C1 . . -107(3)
O5 Li1 O1 C1 2_666 . 27(3)
O5 Li1 O1 C1 . . 130(3)
Li1 Li1 O1 C1 2_666 . 77(3)
Li1 O1 C1 C6 . . 69(3)
Li1 O1 C1 C2 . . -104(3)
O1 C1 C2 C3 . . 178.7(5)
C6 C1 C2 C3 . . 4.7(8)
O1 C1 C2 C7A . . 0(3)
C6 C1 C2 C7A . . -174(3)
O1 C1 C2 Cl2B . . -0.1(8)
C6 C1 C2 Cl2B . . -174.0(5)
C7A C2 C3 C8A . . 4(4)
C1 C2 C3 C8A . . -175(2)
Cl2B C2 C3 C8A . . 4(3)
C7A C2 C3 C4 . . 179(3)
C1 C2 C3 C4 . . 0.1(8)
Cl2B C2 C3 C4 . . 178.9(5)
C1 C2 C3 Cl1B . . -177.9(4)
Cl2B C2 C3 Cl1B . . 0.8(7)
C2 C3 C4 O2 . . 176.6(5)
C8A C3 C4 O2 . . -8(2)
Cl1B C3 C4 O2 . . -5.3(7)
C2 C3 C4 C5 . . -3.7(8)
C8A C3 C4 C5 . . 171(2)
Cl1B C3 C4 C5 . . 174.4(4)
O2 C4 C5 C6 . . -177.9(5)
C3 C4 C5 C6 . . 2.4(8)
O2 C4 C5 C8B . . 3.5(12)
C3 C4 C5 C8B . . -176.2(10)
O2 C4 C5 Cl1A . . 9.8(8)
C3 C4 C5 Cl1A . . -169.9(5)
C8B C5 C6 C1 . . -179.0(11)
C4 C5 C6 C1 . . 2.6(9)
Cl1A C5 C6 C1 . . 174.8(5)
C8B C5 C6 C7B . . -5.3(18)
C4 C5 C6 C7B . . 176.2(13)
C4 C5 C6 Cl2A . . -175.9(6)
Cl1A C5 C6 Cl2A . . -3.6(8)
O1 C1 C6 C5 . . -179.9(6)
C2 C1 C6 C5 . . -6.0(8)
O1 C1 C6 C7B . . 5.9(14)
C2 C1 C6 C7B . . 179.8(12)
O1 C1 C6 Cl2A . . -1.5(9)
C2 C1 C6 Cl2A . . 172.4(5)
O1 Li1 O5 Li1 . 2_666 -111.0(8)
O4 Li1 O5 Li1 . 2_666 119.6(6)
