#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:01:38 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257481 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/00/7240039.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_7240039
loop_
_publ_author_name
'Quarez, Éric'
'Jouhara, Alia'
'Grolleau, Stéphane'
'Dolhem, Franck'
'Dupré, Nicolas'
'Poizot, Philippe'
_publ_section_title
;
 From partial to complete neutralization of 2,5-dihydroxyterephthalic acid
 in the Li--Na system: crystal chemistry and electrochemical behavior of
 Na2Li2C8H2O6vs. Li
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1653
_journal_page_last               1663
_journal_paper_doi               10.1039/C9CE01674K
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C8 H12 Li2 O10'
_chemical_formula_sum            'C8 H12 Li2 O10'
_chemical_formula_weight         282.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2019-05-13 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                97.273(6)
_cell_angle_beta                 110.034(6)
_cell_angle_gamma                111.668(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2720(3)
_cell_length_b                   9.1631(3)
_cell_length_c                   10.5276(12)
_cell_measurement_reflns_used    7903
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      2.2
_cell_volume                     586.18(8)
_computing_cell_refinement       'Dirax/LSQ (Duisenberg et al., 2000)'
_computing_data_collection       'Collect (Nonius BV, 1998)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7903
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.099
_diffrn_reflns_theta_min         2.151
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.9511
_exptl_absorpt_correction_T_min  0.7698
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   Jana2006
_exptl_crystal_colour            light_yellow
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0523P)²+0.2269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2509
_reflns_number_total             3133
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01674k2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7240037--7240040.cif.'
_cod_database_code               7240039
_shelx_shelxl_version_number     2018/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_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
O11 O 0.32538(18) 0.47190(13) 0.86801(10) 0.0264(3) Uani 1 1 d . . . . .
O12 O 0.0775(2) 0.22442(15) 0.72267(12) 0.0387(3) Uani 1 1 d . . . . .
O3 O 0.4560(2) 0.81067(13) 0.53750(12) 0.0352(3) Uani 1 1 d . . . . .
O41 O 0.4102(2) 0.73246(14) 0.28383(12) 0.0327(3) Uani 1 1 d . . . . .
O42 O 0.21485(19) 0.47343(14) 0.14933(11) 0.0286(3) Uani 1 1 d . . . . .
O6 O 0.0234(2) 0.14758(14) 0.46558(12) 0.0347(3) Uani 1 1 d . . . . .
H3 H 0.461(5) 0.814(4) 0.449(3) 0.080(9) Uiso 1 1 d . . . . .
H6 H 0.009(5) 0.135(4) 0.544(3) 0.082(9) Uiso 1 1 d . . . . .
C1 C 0.2218(2) 0.42712(17) 0.62004(14) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.3285(2) 0.59311(18) 0.63329(14) 0.0232(3) Uani 1 1 d . . . . .
H2 H 0.386016 0.669983 0.720171 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3509(2) 0.64622(17) 0.51902(15) 0.0227(3) Uani 1 1 d . . . . .
C4 C 0.2707(2) 0.53062(17) 0.38928(14) 0.0201(3) Uani 1 1 d . . . . .
C5 C 0.1662(2) 0.36480(18) 0.37660(14) 0.0226(3) Uani 1 1 d . . . . .
H5 H 0.115901 0.287606 0.291216 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1353(2) 0.31218(17) 0.48871(14) 0.0222(3) Uani 1 1 d . . . . .
C11 C 0.2060(2) 0.37050(18) 0.74563(15) 0.0231(3) Uani 1 1 d . . . . .
C41 C 0.3000(2) 0.58196(18) 0.26472(14) 0.0218(3) Uani 1 1 d . . . . .
O1 O 0.7372(3) 0.82545(17) 0.98280(15) 0.0431(4) Uani 1 1 d . . . . .
Li1 Li 0.6573(5) 0.5980(3) 0.9598(3) 0.0279(6) Uani 1 1 d . . . . .
H11 H 0.745(4) 0.885(3) 1.049(3) 0.056(7) Uiso 1 1 d . . . . .
H12 H 0.765(4) 0.891(3) 0.934(3) 0.061(7) Uiso 1 1 d . . . . .
O7 O 0.2285(2) 0.73413(15) -0.05040(12) 0.0294(3) Uani 1 1 d . . . . .
O8 O 0.2344(2) 0.97982(16) 0.20123(14) 0.0338(3) Uani 1 1 d . . . . .
O9 O 0.6787(2) 1.01797(16) 0.18934(14) 0.0341(3) Uani 1 1 d . . . . .
Li2 Li 0.3872(5) 0.8563(3) 0.1519(3) 0.0306(6) Uani 1 1 d . . . . .
H71 H 0.275(4) 0.666(3) -0.070(2) 0.040(6) Uiso 1 1 d . . . . .
H72 H 0.092(5) 0.677(3) -0.077(3) 0.062(8) Uiso 1 1 d . . . . .
H81 H 0.130(4) 0.914(3) 0.207(3) 0.060(8) Uiso 1 1 d . . . . .
H82 H 0.325(4) 1.045(3) 0.284(3) 0.056(7) Uiso 1 1 d . . . . .
H91 H 0.775(5) 1.050(3) 0.273(3) 0.063(8) Uiso 1 1 d . . . . .
H92 H 0.707(4) 1.100(3) 0.166(2) 0.047(6) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 '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
_geom_angle_publ_flag
C11 O11 Li1 121.42(13) . 2_667 ?
C11 O11 Li1 127.08(12) . . ?
Li1 O11 Li1 88.52(11) 2_667 . ?
C3 O3 H3 102.6(18) . . ?
C41 O41 Li2 128.93(13) . . ?
C41 O42 Li1 130.98(13) . 2_666 ?
C6 O6 H6 106.6(19) . . ?
C2 C1 C6 119.01(12) . . ?
C2 C1 C11 120.81(12) . . ?
C6 C1 C11 120.14(12) . . ?
C3 C2 C1 121.22(13) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
O3 C3 C2 118.88(13) . . ?
O3 C3 C4 121.56(12) . . ?
C2 C3 C4 119.54(13) . . ?
C5 C4 C3 119.16(12) . . ?
C5 C4 C41 119.43(12) . . ?
C3 C4 C41 121.40(13) . . ?
C6 C5 C4 121.29(13) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
O6 C6 C5 117.51(12) . . ?
O6 C6 C1 122.82(12) . . ?
C5 C6 C1 119.66(13) . . ?
O12 C11 O11 123.91(13) . . ?
O12 C11 C1 117.49(13) . . ?
O11 C11 C1 118.59(13) . . ?
O42 C41 O41 124.23(12) . . ?
O42 C41 C4 118.41(13) . . ?
O41 C41 C4 117.35(12) . . ?
Li1 O1 H11 123.4(19) . . ?
Li1 O1 H12 135.7(18) . . ?
H11 O1 H12 101(3) . . ?
O42 Li1 O1 109.47(13) 2_666 . ?
O42 Li1 O11 118.08(15) 2_666 2_667 ?
O1 Li1 O11 115.35(14) . 2_667 ?
O42 Li1 O11 112.10(14) 2_666 . ?
O1 Li1 O11 108.89(15) . . ?
O11 Li1 O11 91.48(11) 2_667 . ?
O42 Li1 Li1 127.27(18) 2_666 2_667 ?
O1 Li1 Li1 122.51(17) . 2_667 ?
O11 Li1 Li1 46.63(8) 2_667 2_667 ?
O11 Li1 Li1 44.85(9) . 2_667 ?
Li2 O7 H71 110.7(15) . . ?
Li2 O7 H72 113.7(18) . . ?
H71 O7 H72 105(2) . . ?
Li2 O8 H81 106.5(19) . . ?
Li2 O8 H82 104.2(17) . . ?
H81 O8 H82 108(2) . . ?
Li2 O9 H91 116.6(18) . . ?
Li2 O9 H92 126.0(17) . . ?
H91 O9 H92 102(2) . . ?
O41 Li2 O9 109.13(15) . . ?
O41 Li2 O7 117.51(15) . . ?
O9 Li2 O7 109.48(13) . . ?
O41 Li2 O8 103.87(13) . . ?
O9 Li2 O8 106.97(14) . . ?
O7 Li2 O8 109.29(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C11 1.2696(18) . ?
O11 Li1 1.978(3) 2_667 ?
O11 Li1 2.038(3) . ?
O12 C11 1.2501(19) . ?
O3 C3 1.3661(17) . ?
O3 H3 0.95(3) . ?
O41 C41 1.2600(18) . ?
O41 Li2 1.904(3) . ?
O42 C41 1.2539(18) . ?
O42 Li1 1.898(3) 2_666 ?
O6 C6 1.3643(17) . ?
O6 H6 0.88(3) . ?
C1 C2 1.391(2) . ?
C1 C6 1.4010(19) . ?
C1 C11 1.5046(18) . ?
C2 C3 1.3908(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.3998(19) . ?
C4 C5 1.3894(19) . ?
C4 C41 1.5032(17) . ?
C5 C6 1.3863(18) . ?
C5 H5 0.9300 . ?
O1 Li1 1.903(3) . ?
O1 H11 0.79(3) . ?
O1 H12 0.85(3) . ?
Li1 Li1 2.803(5) 2_667 ?
O7 Li2 1.969(3) . ?
O7 H71 0.85(2) . ?
O7 H72 0.85(3) . ?
O8 Li2 1.990(3) . ?
O8 H81 0.80(3) . ?
O8 H82 0.86(3) . ?
O9 Li2 1.950(3) . ?
O9 H91 0.85(3) . ?
O9 H92 0.80(3) . ?
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
O3 H3 O41 0.95(3) 1.66(3) 2.5466(15) 155(3) . yes
O6 H6 O12 0.88(3) 1.77(3) 2.5609(16) 148(3) . yes
O1 H11 O9 0.79(3) 2.10(3) 2.870(2) 165(3) 1_556 yes
O1 H12 O8 0.85(3) 1.97(3) 2.8031(18) 168(2) 2_676 yes
O7 H71 O11 0.85(2) 2.02(2) 2.8548(17) 169(2) 1_554 yes
O7 H72 O42 0.85(3) 1.94(3) 2.7868(17) 173(3) 2_565 yes
O8 H81 O12 0.80(3) 2.01(3) 2.7895(17) 165(3) 2_566 yes
O8 H82 O3 0.86(3) 1.89(3) 2.7473(18) 175(2) 2_676 yes
O9 H91 O6 0.85(3) 2.00(3) 2.8432(18) 173(3) 1_665 yes
O9 H92 O7 0.80(3) 2.08(3) 2.8531(17) 162(2) 2_675 yes
