#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:15:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180419 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/88/7208892.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_7208892
loop_
_publ_author_name
'Molčanov, Krešimir'
'Kojić-Prodić, Biserka'
'Babić, Darko'
'Stare, Jernej'
_publ_section_title
;
 Face-to-face stacking of dianionic quinoid rings in crystals of alkali
 salts of 2,5-dihydroxyquinone in view of π-system polarization
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              135
_journal_paper_doi               10.1039/c2ce26119g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C6 H6 Li2 O6'
_chemical_formula_sum            'C6 H6 Li2 O6'
_chemical_formula_weight         187.99
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_audit_creation_date             2010-03-05T13:39:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 116.462(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9708(7)
_cell_length_b                   6.4417(2)
_cell_length_c                   7.9093(3)
_cell_measurement_reflns_used    1302
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8707
_cell_measurement_theta_min      6.1856
_cell_volume                     728.45(6)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1618
_diffrn_reflns_theta_full        76.05
_diffrn_reflns_theta_max         76.05
_diffrn_reflns_theta_min         6.19
_exptl_absorpt_coefficient_mu    1.305
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.82387
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         818
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0748P)²+0.3598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                758
_reflns_number_total             818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26119g.txt
_cod_data_source_block           li2dhq-3
_cod_original_cell_volume        728.45(5)
_cod_database_code               7208892
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C2B C 0.48352(13) 0 0.6634(2) 0.0196(4) Uani 1 d S
O2B O 0.47926(9) 0 0.81795(17) 0.0262(4) Uani 1 d S
O1B O 0.64860(9) 0 0.84493(17) 0.0240(3) Uani 1 d S
O5 O 0.81246(7) -0.24530(15) 0.80458(14) 0.0286(3) Uani 1 d D
C1B C 0.58289(12) 0 0.6789(2) 0.0187(4) Uani 1 d S
Li2 Li 0.7821(2) 0 0.9281(5) 0.0299(7) Uani 1 d S
Li1 Li 0.3974(2) 0 0.9486(4) 0.0270(7) Uani 1 d S
H3B H 0.3414(17) 0 0.473(4) 0.028(6) Uiso 1 d S
H3A H 0.0074(18) 0 0.816(4) 0.035(7) Uiso 1 d S
H5B H 0.8239(15) -0.191(4) 0.712(3) 0.056(6) Uiso 1 d D
H5A H 0.7580(16) -0.325(5) 0.739(4) 0.100(10) Uiso 1 d D
O1A O 0.16851(9) 0 0.80336(19) 0.0277(4) Uani 1 d S
O2A O 0.16012(10) 0 0.4631(2) 0.0300(4) Uani 1 d S
C2A C 0.08235(13) 0 0.4691(3) 0.0218(4) Uani 1 d S
C1A C 0.08736(13) 0 0.6678(2) 0.0209(4) Uani 1 d S
C3A C 0.00475(13) 0 0.6875(2) 0.0243(4) Uani 1 d S
C3B C 0.40600(12) 0 0.4862(2) 0.0207(4) Uani 1 d S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009 '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'
Li Li 0.001 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.049 0.032 '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
O2B C2B C3B 124.71(16) . .
O2B C2B C1B 115.14(16) . .
C3B C2B C1B 120.15(16) . .
C2B O2B Li1 146.86(15) . .
C2B O2B Li1 115.99(15) . 5_657
Li1 O2B Li1 97.15(13) . 5_657
C1B O1B Li2 129.32(15) . .
C1B O1B Li1 113.45(15) . 5_657
Li2 O1B Li1 117.24(15) . 5_657
Li2 O5 Li1 125.46(12) . 3_545
Li2 O5 H5B 105.8(16) . .
Li1 O5 H5B 115.1(15) 3_545 .
Li2 O5 H5A 109.3(19) . .
Li1 O5 H5A 95(2) 3_545 .
H5B O5 H5A 104(2) . .
O1B C1B C3B 125.44(16) . 5_656
O1B C1B C2B 115.66(15) . .
C3B C1B C2B 118.90(16) 5_656 .
O1A Li2 O1B 103.02(17) 5_657 .
O1A Li2 O5 117.88(11) 5_657 .
O1B Li2 O5 107.49(12) . .
O1A Li2 O5 117.88(11) 5_657 6
O1B Li2 O5 107.49(12) . 6
O5 Li2 O5 102.44(16) . 6
O1A Li2 Li1 70.45(12) 5_657 5_657
O1B Li2 Li1 32.57(9) . 5_657
O5 Li2 Li1 123.31(10) . 5_657
O5 Li2 Li1 123.31(9) 6 5_657
O2B Li1 O2B 82.85(13) . 5_657
O2B Li1 O1B 162.62(18) . 5_657
O2B Li1 O1B 79.77(13) 5_657 5_657
O2B Li1 O5 97.60(11) . 8_445
O2B Li1 O5 128.78(7) 5_657 8_445
O1B Li1 O5 93.29(11) 5_657 8_445
O2B Li1 O5 97.60(11) . 3_455
O2B Li1 O5 128.78(7) 5_657 3_455
O1B Li1 O5 93.29(11) 5_657 3_455
O5 Li1 O5 102.08(14) 8_445 3_455
O2B Li1 Li1 41.63(9) . 5_657
O2B Li1 Li1 41.21(9) 5_657 5_657
O1B Li1 Li1 120.98(19) 5_657 5_657
O5 Li1 Li1 120.48(11) 8_445 5_657
O5 Li1 Li1 120.48(11) 3_455 5_657
O2B Li1 Li2 167.19(15) . 5_657
O2B Li1 Li2 109.96(14) 5_657 5_657
O1B Li1 Li2 30.19(8) 5_657 5_657
O5 Li1 Li2 74.62(10) 8_445 5_657
O5 Li1 Li2 74.62(10) 3_455 5_657
Li1 Li1 Li2 151.17(18) 5_657 5_657
C1A O1A Li2 134.81(16) . 5_657
O2A C2A C3A 125.16(17) . 5_556
O2A C2A C1A 115.73(16) . .
C3A C2A C1A 119.10(16) 5_556 .
O1A C1A C3A 124.71(17) . .
O1A C1A C2A 115.77(16) . .
C3A C1A C2A 119.52(16) . .
C2A C3A C1A 121.37(16) 5_556 .
C2A C3A H3A 118.6(15) 5_556 .
C1A C3A H3A 120.0(15) . .
C1B C3B C2B 120.94(15) 5_656 .
C1B C3B H3B 117.7(15) 5_656 .
C2B C3B H3B 121.3(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2B O2B 1.254(2) .
C2B C3B 1.397(2) .
C2B C1B 1.536(2) .
O2B Li1 1.996(3) .
O2B Li1 2.012(4) 5_657
O1B C1B 1.264(2) .
O1B Li2 1.931(4) .
O1B Li1 2.068(3) 5_657
O5 Li2 2.027(2) .
O5 Li1 2.110(2) 3_545
O5 H5B 0.902(16) .
O5 H5A 0.942(18) .
C1B C3B 1.394(2) 5_656
Li2 O1A 1.908(4) 5_657
Li2 O5 2.027(2) 6
Li2 Li1 3.415(5) 5_657
Li1 O2B 2.012(4) 5_657
Li1 O1B 2.068(3) 5_657
Li1 O5 2.110(2) 8_445
Li1 O5 2.110(2) 3_455
Li1 Li1 3.005(6) 5_657
Li1 Li2 3.415(5) 5_657
O1A C1A 1.261(2) .
O1A Li2 1.908(4) 5_657
O2A C2A 1.264(2) .
C2A C3A 1.391(3) 5_556
C2A C1A 1.537(2) .
C1A C3A 1.396(3) .
C3A C2A 1.391(3) 5_556
C3A H3A 0.99(3) .
C3B C1B 1.394(2) 5_656
C3B H3B 0.99(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C3B C2B O2B Li1 0.0000(10) . .
C1B C2B O2B Li1 180.0000(10) . .
C3B C2B O2B Li1 180 . 5_657
C1B C2B O2B Li1 0 . 5_657
Li2 O1B C1B C3B 0 . 5_656
Li1 O1B C1B C3B 180 5_657 5_656
Li2 O1B C1B C2B 180 . .
Li1 O1B C1B C2B 0 5_657 .
O2B C2B C1B O1B 0 . .
C3B C2B C1B O1B 180 . .
O2B C2B C1B C3B 180 . 5_656
C3B C2B C1B C3B 0 . 5_656
C1B O1B Li2 O1A 180 . 5_657
Li1 O1B Li2 O1A 0 5_657 5_657
C1B O1B Li2 O5 -54.82(11) . .
Li1 O1B Li2 O5 125.18(11) 5_657 .
C1B O1B Li2 O5 54.82(11) . 6
Li1 O1B Li2 O5 -125.18(11) 5_657 6
C1B O1B Li2 Li1 180.000(2) . 5_657
Li1 O5 Li2 O1A -1.6(2) 3_545 5_657
Li1 O5 Li2 O1B -117.28(15) 3_545 .
Li1 O5 Li2 O5 129.62(13) 3_545 6
Li1 O5 Li2 Li1 -85.5(2) 3_545 5_657
C2B O2B Li1 O2B 180.0000(10) . 5_657
Li1 O2B Li1 O2B 0 5_657 5_657
C2B O2B Li1 O1B 180.0000(10) . 5_657
Li1 O2B Li1 O1B 0.000(2) 5_657 5_657
C2B O2B Li1 O5 51.67(8) . 8_445
Li1 O2B Li1 O5 -128.33(8) 5_657 8_445
C2B O2B Li1 O5 -51.67(8) . 3_455
Li1 O2B Li1 O5 128.33(8) 5_657 3_455
C2B O2B Li1 Li1 180.0000(10) . 5_657
C2B O2B Li1 Li2 0.000(4) . 5_657
Li1 O2B Li1 Li2 180.000(3) 5_657 5_657
Li2 O1A C1A C3A 0 5_657 .
Li2 O1A C1A C2A 180 5_657 .
O2A C2A C1A O1A 0 . .
C3A C2A C1A O1A 180 5_556 .
O2A C2A C1A C3A 180 . .
C3A C2A C1A C3A 0 5_556 .
O1A C1A C3A C2A 180 . 5_556
C2A C1A C3A C2A 0 . 5_556
O2B C2B C3B C1B 180 . 5_656
C1B C2B C3B C1B 0 . 5_656
