#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:01:38 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257481 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/00/7240037.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_7240037
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                104.049(10)
_cell_angle_beta                 97.995(6)
_cell_angle_gamma                96.617(7)
_cell_formula_units_Z            2
_cell_length_a                   7.1646(4)
_cell_length_b                   8.5039(11)
_cell_length_c                   10.0021(11)
_cell_measurement_reflns_used    6884
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      2.1
_cell_volume                     578.34(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6884
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_min         2.131
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9698
_exptl_absorpt_correction_T_min  0.8661
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   Jana2006
_exptl_crystal_colour            light_yellow
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0481
_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)+(0.0365P)²+0.3655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2175
_reflns_number_total             3066
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01674k2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7240037--7240040.cif.'
_cod_database_code               7240037
_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 0.7437(2) 0.39718(15) 0.86410(12) 0.0270(3) Uani 1 1 d . . . . .
O12 O 0.7514(2) 0.16260(15) 0.71065(13) 0.0291(3) Uani 1 1 d . . . . .
O3 O 0.7309(2) 0.80664(15) 0.57652(14) 0.0299(3) Uani 1 1 d . . . . .
H3 H 0.734(4) 0.832(4) 0.493(3) 0.070(9) Uiso 1 1 d . . . . .
O41 O 0.7458(2) 0.78625(16) 0.32005(14) 0.0331(3) Uani 1 1 d . . . . .
O42 O 0.7485(2) 0.54702(16) 0.16909(12) 0.0279(3) Uani 1 1 d . . . . .
O6 O 0.7780(2) 0.14562(15) 0.46259(14) 0.0296(3) Uani 1 1 d . . . . .
H6 H 0.766(4) 0.123(4) 0.550(3) 0.067(9) Uiso 1 1 d . . . . .
C1 C 0.7487(2) 0.39799(19) 0.62614(16) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.7366(2) 0.5642(2) 0.64981(17) 0.0197(4) Uani 1 1 d . . . . .
H2 H 0.726599 0.624296 0.738871 0.024 Uiso 1 1 calc R U . . .
C3 C 0.7392(2) 0.6418(2) 0.54381(17) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.7516(2) 0.5526(2) 0.40797(17) 0.0177(3) Uani 1 1 d . . . . .
C5 C 0.7651(2) 0.3872(2) 0.38440(17) 0.0202(4) Uani 1 1 d . . . . .
H5 H 0.775636 0.327394 0.295364 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7634(2) 0.3091(2) 0.49099(17) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.7473(2) 0.3158(2) 0.74213(17) 0.0193(3) Uani 1 1 d . . . . .
C41 C 0.7491(2) 0.6335(2) 0.28997(18) 0.0207(4) Uani 1 1 d . . . . .
O1 O 0.5408(2) 0.72223(19) 0.94515(16) 0.0297(3) Uani 1 1 d . . . . .
H11 H 0.444(4) 0.645(4) 0.906(3) 0.066(9) Uiso 1 1 d . . . . .
H12 H 0.512(4) 0.782(4) 1.012(3) 0.068(10) Uiso 1 1 d . . . . .
O2 O 0.9934(2) 0.75797(18) 0.99937(15) 0.0302(3) Uani 1 1 d D . . . .
H21 H 1.009(6) 0.800(5) 0.930(3) 0.133(17) Uiso 1 1 d D . . . .
H22 H 1.084(5) 0.714(4) 1.027(4) 0.085(12) Uiso 1 1 d . . . . .
Li1 Li 0.7580(5) 0.6069(4) 0.9956(3) 0.0270(7) Uani 1 1 d . . . . .
O4 O 0.9662(2) 1.05362(18) 0.19522(15) 0.0298(3) Uani 1 1 d D . . . .
H41 H 0.986(7) 0.961(4) 0.146(5) 0.17(2) Uiso 1 1 d D . . . .
H42 H 1.061(4) 1.087(4) 0.261(3) 0.073(10) Uiso 1 1 d . . . . .
O5 O 0.5012(2) 0.99349(19) 0.16800(16) 0.0327(3) Uani 1 1 d . . . . .
H51 H 0.477(4) 1.081(3) 0.151(3) 0.049(8) Uiso 1 1 d . . . . .
H52 H 0.401(4) 0.953(4) 0.209(3) 0.074(10) Uiso 1 1 d . . . . .
Li2 Li 0.7462(5) 0.9906(4) 0.2788(3) 0.0286(7) Uani 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 149.20(15) . . ?
C3 O3 H3 103.3(19) . . ?
C41 O41 Li2 154.12(16) . . ?
C41 O42 Li1 130.79(15) . 1_554 ?
C6 O6 Li2 127.25(14) . 1_545 ?
C6 O6 H6 101.5(18) . . ?
Li2 O6 H6 128.6(18) 1_545 . ?
C2 C1 C6 118.61(15) . . ?
C2 C1 C11 120.74(14) . . ?
C6 C1 C11 120.65(14) . . ?
C3 C2 C1 121.29(15) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
O3 C3 C2 117.65(15) . . ?
O3 C3 C4 122.15(15) . . ?
C2 C3 C4 120.21(15) . . ?
C5 C4 C3 118.59(15) . . ?
C5 C4 C41 120.28(14) . . ?
C3 C4 C41 121.13(15) . . ?
C4 C5 C6 121.29(15) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
O6 C6 C5 119.10(14) . . ?
O6 C6 C1 120.90(15) . . ?
C5 C6 C1 120.00(15) . . ?
O11 C11 O12 122.74(16) . . ?
O11 C11 C1 120.46(15) . . ?
O12 C11 C1 116.79(14) . . ?
O42 C41 O41 124.15(16) . . ?
O42 C41 C4 118.85(15) . . ?
O41 C41 C4 116.99(15) . . ?
Li1 O1 H11 105(2) . . ?
Li1 O1 H12 113(2) . . ?
H11 O1 H12 108(3) . . ?
Li1 O2 H21 122(3) . . ?
Li1 O2 H22 106(2) . . ?
H21 O2 H22 115(4) . . ?
O11 Li1 O42 102.23(16) . 1_556 ?
O11 Li1 O2 111.73(16) . . ?
O42 Li1 O2 113.61(17) 1_556 . ?
O11 Li1 O1 111.81(17) . . ?
O42 Li1 O1 112.11(16) 1_556 . ?
O2 Li1 O1 105.55(16) . . ?
Li2 O4 H41 103(4) . . ?
Li2 O4 H42 107(2) . . ?
H41 O4 H42 106(4) . . ?
Li2 O5 H51 119.0(18) . . ?
Li2 O5 H52 109.8(19) . . ?
H51 O5 H52 108(2) . . ?
O41 Li2 O5 109.40(18) . . ?
O41 Li2 O6 103.48(16) . 1_565 ?
O5 Li2 O6 110.18(17) . 1_565 ?
O41 Li2 O4 113.32(17) . . ?
O5 Li2 O4 113.67(17) . . ?
O6 Li2 O4 106.23(17) 1_565 . ?
O41 Li2 H41 95.4(10) . . ?
O5 Li2 H41 112.5(13) . . ?
O6 Li2 H41 123.5(10) 1_565 . ?
O4 Li2 H41 21.2(9) . . ?
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 1.253(2) . ?
O11 Li1 1.924(3) . ?
O12 C11 1.269(2) . ?
O3 C3 1.370(2) . ?
O3 H3 0.91(3) . ?
O41 C41 1.264(2) . ?
O41 Li2 1.881(3) . ?
O42 C41 1.252(2) . ?
O42 Li1 1.931(3) 1_554 ?
O6 C6 1.369(2) . ?
O6 Li2 1.951(3) 1_545 ?
O6 H6 0.95(3) . ?
C1 C2 1.391(2) . ?
C1 C6 1.404(2) . ?
C1 C11 1.493(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(2) . ?
C4 C5 1.386(2) . ?
C4 C41 1.502(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9300 . ?
O1 Li1 2.003(4) . ?
O1 H11 0.87(3) . ?
O1 H12 0.80(3) . ?
O2 Li1 1.989(4) . ?
O2 H21 0.869(19) . ?
O2 H22 0.83(4) . ?
O4 Li2 1.965(4) . ?
O4 H41 0.859(19) . ?
O4 H42 0.85(3) . ?
O5 Li2 1.947(4) . ?
O5 H51 0.83(3) . ?
O5 H52 0.95(3) . ?
Li2 H41 2.32(5) . ?
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 0.91(3) 1.70(3) 2.5468(19) 153(3) . yes
O6 H6 O12 0.95(3) 1.58(3) 2.4853(18) 157(3) . yes
C2 H2 O1 0.93 2.63 3.487(2) 153.8 . yes
O1 H11 O42 0.87(3) 1.93(3) 2.797(2) 172(3) 2_666 yes
O1 H12 O5 0.80(3) 2.09(3) 2.864(2) 161(3) 1_556 yes
O2 H21 O4 0.869(19) 1.98(2) 2.829(2) 165(4) 2_776 yes
O2 H22 O11 0.83(4) 2.00(4) 2.808(2) 164(3) 2_767 yes
O2 H22 O12 0.83(4) 2.62(3) 3.082(2) 116(3) 2_767 yes
O4 H41 O2 0.859(19) 1.99(2) 2.833(2) 168(5) 1_554 yes
O4 H42 O3 0.85(3) 1.99(3) 2.836(2) 172(3) 2_776 yes
O5 H51 O1 0.83(3) 2.13(3) 2.935(2) 162(2) 2_676 yes
O5 H52 O12 0.95(3) 1.78(4) 2.711(2) 165(3) 2_666 yes
