# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1915719'
loop_
_audit_author_name
_audit_author_address
'Eric Quarez'
;Institut des Materiaux Jean Rouxel (IMN)
France
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Li2 O10'
_chemical_formula_sum            'C8 H12 Li2 O10'
_chemical_formula_weight         282.06

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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'

_cell_length_a                   7.1646(4)
_cell_length_b                   8.5039(11)
_cell_length_c                   10.0021(11)
_cell_angle_alpha                104.049(10)
_cell_angle_beta                 97.995(6)
_cell_angle_gamma                96.617(7)
_cell_volume                     578.34(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    6884
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      29.0

_exptl_crystal_description       needle
_exptl_crystal_colour            light_yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.8661
_exptl_absorpt_correction_T_max  0.9698
_exptl_absorpt_process_details   Jana2006
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6884
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.131
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3066
_reflns_number_gt                2175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1998)'
_computing_cell_refinement       'Dirax/LSQ (Duisenberg et al., 2000)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+0.3655P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3066
_refine_ls_number_parameters     222
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.083


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1915721'
loop_
_audit_author_name
_audit_author_address
'Eric Quarez'
;Institut des Materiaux Jean Rouxel (IMN)
France
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H18 Li2 Na2 O14'
_chemical_formula_sum            'C8 H18 Li2 Na2 O14'
_chemical_formula_weight         398.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Na Na 0.0362 0.0249 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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'

_cell_length_a                   7.3738(11)
_cell_length_b                   7.4503(14)
_cell_length_c                   8.1802(8)
_cell_angle_alpha                76.479(13)
_cell_angle_beta                 66.792(8)
_cell_angle_gamma                84.39(2)
_cell_volume                     401.58(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      35.0

_exptl_crystal_description       block
_exptl_crystal_colour            light_green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             206
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.246
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.9471
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_process_details   Jana2006
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9917
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.773
_diffrn_reflns_theta_max         34.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3489
_reflns_number_gt                2842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1998)'
_computing_cell_refinement       'Dirax/LSQ (Duisenberg et al., 2000)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.1202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.048(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3489
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Na1 Na 0.58606(6) 0.49117(6) 0.75775(6) 0.02379(11) Uani 1 1 d . . . . .
O1 O 0.44893(12) 0.29755(11) 1.04082(11) 0.02337(15) Uani 1 1 d . . . . .
H11 H 0.513(3) 0.204(3) 1.053(2) 0.042(5) Uiso 1 1 d . . . . .
H12 H 0.330(3) 0.259(2) 1.073(2) 0.039(4) Uiso 1 1 d . . . . .
O2 O 0.79663(12) 0.65539(13) 0.45907(12) 0.02708(17) Uani 1 1 d . . . . .
H21 H 0.829(3) 0.754(3) 0.467(3) 0.057(6) Uiso 1 1 d . . . . .
H22 H 0.696(3) 0.682(3) 0.433(3) 0.051(5) Uiso 1 1 d . . . . .
Li1 Li 0.8446(3) 0.2458(3) 0.0824(2) 0.0212(3) Uani 1 1 d . . . . .
O4 O 0.89822(12) 0.42573(12) 0.84803(11) 0.02550(16) Uani 1 1 d . . . . .
H41 H 0.920(3) 0.533(3) 0.851(3) 0.055(6) Uiso 1 1 d . . . . .
H42 H 0.991(3) 0.400(3) 0.760(3) 0.046(5) Uiso 1 1 d . . . . .
O5 O 0.72295(12) 0.01389(11) 0.09428(11) 0.02512(16) Uani 1 1 d . . . . .
H51 H 0.790(3) -0.052(3) 0.020(3) 0.049(5) Uiso 1 1 d . . . . .
H52 H 0.651(3) -0.058(3) 0.190(3) 0.043(5) Uiso 1 1 d . . . . .
O11 O 0.53809(10) 0.26105(11) 0.60361(9) 0.02187(15) Uani 1 1 d . . . . .
O12 O 0.32419(11) 0.68228(11) 0.69826(9) 0.02218(15) Uani 1 1 d . . . . .
O3 O 1.06774(9) 0.19613(9) 0.14756(8) 0.01711(13) Uani 1 1 d . . . . .
C1 C 0.85113(12) 0.12288(11) 0.46948(11) 0.01353(14) Uani 1 1 d . . . . .
C2 C 0.83164(12) 0.02338(12) 0.64327(11) 0.01530(15) Uani 1 1 d . . . . .
H2 H 0.717105 0.041342 0.740853 0.018 Uiso 1 1 calc R U . . .
C3 C 1.02722(12) 0.10177(12) 0.31907(11) 0.01351(14) Uani 1 1 d . . . . .
C11 C 0.67785(12) 0.24327(12) 0.45540(11) 0.01482(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Na1 O1 2.3115(10) . ?
Na1 O2 2.4209(11) . ?
Na1 O12 2.4233(9) . ?
Na1 O1 2.4612(10) 2_667 ?
Na1 O11 2.4769(10) . ?
Na1 O4 2.6521(10) . ?
Na1 Li1 3.5135(19) 2_666 ?
Na1 Na1 3.6855(9) 2_667 ?
Na1 H22 2.546(19) . ?
O1 H11 0.811(19) . ?
O1 H12 0.869(18) . ?
O2 H21 0.82(2) . ?
O2 H22 0.84(2) . ?
Li1 O3 1.8995(18) . ?
Li1 O12 1.9013(19) 2_666 ?
Li1 O4 1.9833(19) 1_554 ?
Li1 O5 1.989(2) . ?
Li1 C3 2.7411(19) . ?
O4 H41 0.84(2) . ?
O4 H42 0.82(2) . ?
O5 H51 0.84(2) . ?
O5 H52 0.843(19) . ?
O11 C11 1.2701(11) . ?
O12 C11 1.2550(11) 2_666 ?
O3 C3 1.3421(10) . ?
C1 C2 1.3994(12) . ?
C1 C3 1.4199(11) . ?
C1 C11 1.5146(12) . ?
C2 C3 1.4058(12) 2_756 ?
C2 H2 0.9300 . ?

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
O1 Na1 O2 167.14(4) . . ?
O1 Na1 O12 107.99(3) . . ?
O2 Na1 O12 84.85(3) . . ?
O1 Na1 O1 78.94(3) . 2_667 ?
O2 Na1 O1 104.22(4) . 2_667 ?
O12 Na1 O1 82.58(3) . 2_667 ?
O1 Na1 O11 91.93(3) . . ?
O2 Na1 O11 86.95(3) . . ?
O12 Na1 O11 90.65(3) . . ?
O1 Na1 O11 166.27(3) 2_667 . ?
O1 Na1 O4 79.64(3) . . ?
O2 Na1 O4 89.11(3) . . ?
O12 Na1 O4 154.24(3) . . ?
O1 Na1 O4 74.67(3) 2_667 . ?
O11 Na1 O4 114.05(3) . . ?
O1 Na1 Li1 83.87(4) . 2_666 ?
O2 Na1 Li1 108.49(4) . 2_666 ?
O12 Na1 Li1 30.96(3) . 2_666 ?
O1 Na1 Li1 58.16(4) 2_667 2_666 ?
O11 Na1 Li1 111.06(4) . 2_666 ?
O4 Na1 Li1 132.18(4) . 2_666 ?
O1 Na1 Na1 40.95(2) . 2_667 ?
O2 Na1 Na1 140.85(3) . 2_667 ?
O12 Na1 Na1 96.17(3) . 2_667 ?
O1 Na1 Na1 37.99(2) 2_667 2_667 ?
O11 Na1 Na1 132.06(3) . 2_667 ?
O4 Na1 Na1 73.18(2) . 2_667 ?
Li1 Na1 Na1 65.21(3) 2_666 2_667 ?
O1 Na1 H22 170.7(5) . . ?
O2 Na1 H22 19.2(5) . . ?
O12 Na1 H22 67.0(5) . . ?
O1 Na1 H22 107.5(5) 2_667 . ?
O11 Na1 H22 80.5(5) . . ?
O4 Na1 H22 108.3(5) . . ?
Li1 Na1 H22 93.8(4) 2_666 . ?
Na1 Na1 H22 145.1(5) 2_667 . ?
Na1 O1 Na1 101.06(3) . 2_667 ?
Na1 O1 H11 113.1(13) . . ?
Na1 O1 H11 116.7(13) 2_667 . ?
Na1 O1 H12 117.0(11) . . ?
Na1 O1 H12 104.5(11) 2_667 . ?
H11 O1 H12 104.6(16) . . ?
Na1 O2 H21 109.3(14) . . ?
Na1 O2 H22 88.8(13) . . ?
H21 O2 H22 104.2(18) . . ?
O3 Li1 O12 95.48(8) . 2_666 ?
O3 Li1 O4 113.35(9) . 1_554 ?
O12 Li1 O4 118.75(10) 2_666 1_554 ?
O3 Li1 O5 111.42(9) . . ?
O12 Li1 O5 103.25(9) 2_666 . ?
O4 Li1 O5 113.04(9) 1_554 . ?
O3 Li1 C3 26.49(4) . . ?
O12 Li1 C3 76.48(6) 2_666 . ?
O4 Li1 C3 139.13(9) 1_554 . ?
O5 Li1 C3 97.79(7) . . ?
O3 Li1 Na1 132.53(8) . 2_666 ?
O12 Li1 Na1 40.97(4) 2_666 2_666 ?
O4 Li1 Na1 84.57(6) 1_554 2_666 ?
O5 Li1 Na1 99.17(7) . 2_666 ?
C3 Li1 Na1 117.36(6) . 2_666 ?
Li1 O4 Na1 112.95(6) 1_556 . ?
Li1 O4 H41 113.9(14) 1_556 . ?
Na1 O4 H41 99.6(13) . . ?
Li1 O4 H42 115.8(13) 1_556 . ?
Na1 O4 H42 107.6(13) . . ?
H41 O4 H42 105.6(18) . . ?
Li1 O5 H51 117.2(13) . . ?
Li1 O5 H52 126.2(13) . . ?
H51 O5 H52 107.3(18) . . ?
C11 O11 Na1 116.53(6) . . ?
C11 O12 Li1 123.77(8) 2_666 2_666 ?
C11 O12 Na1 126.33(6) 2_666 . ?
Li1 O12 Na1 108.07(6) 2_666 . ?
C3 O3 Li1 114.37(8) . . ?
C2 C1 C3 118.66(7) . . ?
C2 C1 C11 116.82(7) . . ?
C3 C1 C11 124.51(7) . . ?
C1 C2 C3 124.69(8) . 2_756 ?
C1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 2_756 . ?
O3 C3 C2 119.01(7) . 2_756 ?
O3 C3 C1 124.33(7) . . ?
C2 C3 C1 116.63(7) 2_756 . ?
C2 C3 Li1 146.81(7) 2_756 . ?
C1 C3 Li1 90.68(6) . . ?
O12 C11 O11 123.05(8) 2_666 . ?
O12 C11 C1 119.84(7) 2_666 . ?
O11 C11 C1 117.09(7) . . ?

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
O1 H11 O5 0.811(19) 2.068(19) 2.8583(13) 164.7(17) 1_556 yes
O1 H12 O3 0.869(18) 1.855(18) 2.7214(11) 174.8(17) 1_456 yes
O4 H41 O3 0.84(2) 2.03(2) 2.8625(13) 171.1(19) 2_766 yes
O4 H42 O2 0.82(2) 1.96(2) 2.7800(13) 176.5(18) 2_766 yes
O5 H51 O3 0.84(2) 1.86(2) 2.7042(12) 177.8(19) 2_755 yes
O5 H52 O11 0.843(19) 2.11(2) 2.9432(13) 169.8(17) 2_656 yes

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1915720'
loop_
_audit_author_name
_audit_author_address
'Eric Quarez'
;Institut des Materiaux Jean Rouxel (IMN)
France
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Li2 O10'
_chemical_formula_sum            'C8 H12 Li2 O10'
_chemical_formula_weight         282.06

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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'

_cell_length_a                   7.2720(3)
_cell_length_b                   9.1631(3)
_cell_length_c                   10.5276(12)
_cell_angle_alpha                97.273(6)
_cell_angle_beta                 110.034(6)
_cell_angle_gamma                111.668(3)
_cell_volume                     586.18(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    7903
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      29.1

_exptl_crystal_description       needle
_exptl_crystal_colour            light_yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.7698
_exptl_absorpt_correction_T_max  0.9511
_exptl_absorpt_process_details   Jana2006
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7903
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         29.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3133
_reflns_number_gt                2509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1998)'
_computing_cell_refinement       'Dirax/LSQ (Duisenberg et al., 2000)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.2269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3133
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.088


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1915722'
loop_
_audit_author_name
_audit_author_address
'Eric Quarez'
;Institut des Materiaux Jean Rouxel (IMN)
France
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_shelx               
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: H-atoms, located in difference Fourier maps and freely refined, indicate that symmetry is indeed P-1.
;
_vrf_PLAT112_shelx               
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       a/2        100 %Fit
RESPONSE: H-atoms, located in difference Fourier maps and freely refined, indicate that symmetry is indeed P-1.
;
_vrf_PLAT112_shelx_2             
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         c        100 %Fit
RESPONSE: H-atoms, located in difference Fourier maps and freely refined, indicate that symmetry is indeed P-1.
;
_vrf_PLAT113_shelx               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       C2/c Check
RESPONSE: H-atoms, located in difference Fourier maps and freely refined, indicate that symmetry is indeed P-1.
;
# Added during the CSD deposition process: Monday 13 May 2019 01:48 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Na2 O10'
_chemical_formula_sum            'C8 H12 Na2 O10'
_chemical_formula_weight         314.16

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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'

_cell_length_a                   7.3226(11)
_cell_length_b                   9.2359(5)
_cell_length_c                   18.444(2)
_cell_angle_alpha                100.611(6)
_cell_angle_beta                 90.051(12)
_cell_angle_gamma                101.428(11)
_cell_volume                     1200.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    18849
_cell_measurement_theta_min      1.1
_cell_measurement_theta_max      31.5

_exptl_crystal_description       needle
_exptl_crystal_colour            light_yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.9293
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_process_details   Jana2006
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18849
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.124
_diffrn_reflns_theta_max         31.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7947
_reflns_number_gt                4397
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1998)'
_computing_cell_refinement       'Dirax/LSQ (Duisenberg et al., 2000)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+0.7247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7947
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1593
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Na1A Na 0.54425(12) -0.16398(10) 0.36871(5) 0.0245(2) Uani 1 1 d . . . . .
Na2A Na 0.04610(12) -0.15606(10) 0.37125(5) 0.0257(2) Uani 1 1 d . . . . .
O2A O 0.2704(2) 0.76415(17) 0.44763(8) 0.0239(3) Uani 1 1 d . . . . .
H2A H 0.320(5) 0.834(4) 0.4818(19) 0.054(10) Uiso 1 1 d . . . . .
O5A O 0.2337(2) 0.24072(17) 0.55703(8) 0.0248(3) Uani 1 1 d . . . . .
H5A H 0.195(5) 0.169(4) 0.518(2) 0.062(10) Uiso 1 1 d . . . . .
O11A O 0.4147(2) 0.90699(17) 0.56850(8) 0.0286(4) Uani 1 1 d . . . . .
O12A O 0.4820(2) 0.79304(17) 0.65823(8) 0.0279(4) Uani 1 1 d . . . . .
O41A O 0.0306(3) 0.21231(17) 0.34604(8) 0.0319(4) Uani 1 1 d . . . . .
O42A O 0.0970(2) 0.09818(17) 0.43570(8) 0.0290(4) Uani 1 1 d . . . . .
C1A C 0.3294(3) 0.6412(2) 0.54771(10) 0.0176(4) Uani 1 1 d . . . . .
C2A C 0.2622(3) 0.6357(2) 0.47552(11) 0.0184(4) Uani 1 1 d . . . . .
C3A C 0.1868(3) 0.4980(2) 0.43138(11) 0.0194(4) Uani 1 1 d . . . . .
H3A H 0.142666 0.494789 0.383705 0.023 Uiso 1 1 calc R U . . .
C4A C 0.1764(3) 0.3645(2) 0.45743(10) 0.0176(4) Uani 1 1 d . . . . .
C5A C 0.2429(3) 0.3707(2) 0.52980(11) 0.0178(4) Uani 1 1 d . . . . .
C6A C 0.3181(3) 0.5076(2) 0.57383(11) 0.0198(4) Uani 1 1 d . . . . .
H6A H 0.361689 0.510578 0.621568 0.024 Uiso 1 1 calc R U . . .
C11A C 0.4145(3) 0.7898(2) 0.59513(11) 0.0203(4) Uani 1 1 d . . . . .
C41A C 0.0954(3) 0.2157(2) 0.40925(11) 0.0209(4) Uani 1 1 d . . . . .
O1A O 0.3100(2) -0.0882(2) 0.30342(10) 0.0273(4) Uani 1 1 d . . . . .
O3A O -0.0490(3) -0.3536(2) 0.26261(11) 0.0364(4) Uani 1 1 d . . . . .
O4A O 0.5601(3) -0.3573(2) 0.26486(10) 0.0383(5) Uani 1 1 d . . . . .
O6A O -0.1915(2) -0.0666(2) 0.30720(10) 0.0260(4) Uani 1 1 d . . . . .
H11A H 0.302(4) -0.114(4) 0.2603(19) 0.045(9) Uiso 1 1 d . . . . .
H12A H 0.356(4) -0.001(4) 0.3102(18) 0.044(9) Uiso 1 1 d . . . . .
H31A H 0.004(5) -0.314(4) 0.223(2) 0.067(11) Uiso 1 1 d . . . . .
H32A H -0.169(6) -0.353(4) 0.262(2) 0.088(14) Uiso 1 1 d . . . . .
H41A H 0.495(5) -0.453(4) 0.256(2) 0.073(11) Uiso 1 1 d . . . . .
H42A H 0.554(5) -0.320(4) 0.225(2) 0.057(10) Uiso 1 1 d . . . . .
H61A H -0.201(4) -0.083(3) 0.2645(18) 0.034(8) Uiso 1 1 d . . . . .
H62A H -0.139(5) 0.019(4) 0.3190(18) 0.050(10) Uiso 1 1 d . . . . .
Na1B Na 0.62750(12) -0.15512(10) 0.87132(5) 0.0252(2) Uani 1 1 d . . . . .
Na2B Na 0.12157(12) -0.16472(9) 0.86843(5) 0.0242(2) Uani 1 1 d . . . . .
O2B O 0.3615(2) 0.75506(17) 0.94587(8) 0.0245(3) Uani 1 1 d . . . . .
H2B H 0.358(5) 0.824(4) 0.9826(19) 0.051(9) Uiso 1 1 d . . . . .
O5B O 0.1364(2) 0.23107(17) 1.05478(8) 0.0235(3) Uani 1 1 d . . . . .
H5B H 0.144(5) 0.162(4) 1.0192(19) 0.053(10) Uiso 1 1 d . . . . .
O11B O 0.2943(2) 0.89705(17) 1.06803(9) 0.0292(4) Uani 1 1 d . . . . .
O12B O 0.1684(2) 0.78086(17) 1.15693(8) 0.0287(4) Uani 1 1 d . . . . .
O41B O 0.3298(2) 0.20102(17) 0.84441(8) 0.0292(4) Uani 1 1 d . . . . .
O42B O 0.2070(2) 0.08887(16) 0.93472(8) 0.0282(4) Uani 1 1 d . . . . .
C1B C 0.2419(3) 0.6311(2) 1.04561(10) 0.0180(4) Uani 1 1 d . . . . .
C2B C 0.3062(3) 0.6256(2) 0.97355(11) 0.0179(4) Uani 1 1 d . . . . .
C3B C 0.3125(3) 0.4879(2) 0.92920(11) 0.0194(4) Uani 1 1 d . . . . .
H3B H 0.354216 0.485042 0.881451 0.023 Uiso 1 1 calc R U . . .
C4B C 0.2573(3) 0.3545(2) 0.95507(10) 0.0175(4) Uani 1 1 d . . . . .
C5B C 0.1929(3) 0.3603(2) 1.02726(11) 0.0181(4) Uani 1 1 d . . . . .
C6B C 0.1861(3) 0.4979(2) 1.07156(11) 0.0192(4) Uani 1 1 d . . . . .
H6B H 0.143747 0.500843 1.119218 0.023 Uiso 1 1 calc R U . . .
C11B C 0.2338(3) 0.7796(2) 1.09395(11) 0.0204(4) Uani 1 1 d . . . . .
C41B C 0.2655(3) 0.2055(2) 0.90765(11) 0.0204(4) Uani 1 1 d . . . . .
O1B O 0.3964(2) -0.0895(2) 0.80477(10) 0.0264(4) Uani 1 1 d . . . . .
O3B O 0.0096(3) -0.3585(2) 0.76574(10) 0.0380(5) Uani 1 1 d . . . . .
O4B O 0.6215(3) -0.3536(2) 0.76241(11) 0.0356(4) Uani 1 1 d . . . . .
O6B O -0.0929(2) -0.0654(2) 0.80578(10) 0.0259(3) Uani 1 1 d . . . . .
H11B H 0.407(4) -0.111(4) 0.7630(19) 0.043(9) Uiso 1 1 d . . . . .
H12B H 0.398(5) -0.004(4) 0.8137(18) 0.045(10) Uiso 1 1 d . . . . .
H31B H 0.030(5) -0.456(5) 0.754(2) 0.078(12) Uiso 1 1 d . . . . .
H32B H 0.031(5) -0.327(4) 0.724(2) 0.060(10) Uiso 1 1 d . . . . .
H41B H 0.743(6) -0.362(5) 0.762(2) 0.097(15) Uiso 1 1 d . . . . .
H42B H 0.589(5) -0.316(4) 0.725(2) 0.069(12) Uiso 1 1 d . . . . .
H61B H -0.098(4) -0.083(3) 0.7629(18) 0.038(8) Uiso 1 1 d . . . . .
H62B H -0.100(5) 0.024(4) 0.8153(19) 0.057(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Na1A O6A 2.3519(19) 1_655 ?
Na1A O1A 2.3797(19) . ?
Na1A O4A 2.386(2) . ?
Na1A O11A 2.4019(18) 2_666 ?
Na1A O5A 2.4149(17) 2_656 ?
Na1A O2A 2.5325(18) 1_545 ?
Na1A Na2A 3.6612(13) 1_655 ?
Na1A Na2A 3.6631(13) . ?
Na1A H12A 2.60(3) . ?
Na2A O1A 2.3466(19) . ?
Na2A O42A 2.3854(18) . ?
Na2A O3A 2.445(2) . ?
Na2A O6A 2.4554(19) . ?
Na2A O2A 2.4666(17) 1_545 ?
Na2A O5A 2.5121(18) 2_556 ?
Na2A H62A 2.61(3) . ?
O2A C2A 1.369(2) . ?
O2A H2A 0.84(4) . ?
O5A C5A 1.374(2) . ?
O5A H5A 0.89(4) . ?
O11A C11A 1.268(2) . ?
O12A C11A 1.257(2) . ?
O41A C41A 1.251(2) . ?
O42A C41A 1.272(2) . ?
C1A C6A 1.394(3) . ?
C1A C2A 1.408(3) . ?
C1A C11A 1.502(3) . ?
C2A C3A 1.387(3) . ?
C3A C4A 1.392(3) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.408(3) . ?
C4A C41A 1.502(3) . ?
C5A C6A 1.380(3) . ?
C6A H6A 0.9300 . ?
O1A H11A 0.79(3) . ?
O1A H12A 0.79(3) . ?
O3A H31A 0.93(4) . ?
O3A H32A 0.88(4) . ?
O4A H41A 0.90(4) . ?
O4A H42A 0.87(4) . ?
O6A H61A 0.77(3) . ?
O6A H62A 0.79(3) . ?
Na1B O1B 2.3272(19) . ?
Na1B O11B 2.3951(18) 2_667 ?
Na1B O4B 2.451(2) . ?
Na1B O6B 2.4578(19) 1_655 ?
Na1B O2B 2.4813(17) 1_545 ?
Na1B O5B 2.4836(18) 2_657 ?
Na1B Na2B 3.6366(13) 1_655 ?
Na1B Na2B 3.6883(13) . ?
Na2B O6B 2.3669(19) . ?
Na2B O3B 2.373(2) . ?
Na2B O1B 2.3794(19) . ?
Na2B O42B 2.3948(17) . ?
Na2B O5B 2.4114(17) 2_557 ?
Na2B O2B 2.5647(18) 1_545 ?
Na2B H12B 2.59(3) . ?
O2B C2B 1.374(2) . ?
O2B H2B 0.84(3) . ?
O5B C5B 1.372(2) . ?
O5B H5B 0.84(4) . ?
O11B C11B 1.265(2) . ?
O12B C11B 1.256(2) . ?
O41B C41B 1.255(2) . ?
O42B C41B 1.268(2) . ?
C1B C6B 1.388(3) . ?
C1B C2B 1.406(3) . ?
C1B C11B 1.504(3) . ?
C2B C3B 1.388(3) . ?
C3B C4B 1.389(3) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.408(3) . ?
C4B C41B 1.500(3) . ?
C5B C6B 1.388(3) . ?
C6B H6B 0.9300 . ?
O1B H11B 0.77(3) . ?
O1B H12B 0.77(4) . ?
O3B H31B 0.93(4) . ?
O3B H32B 0.87(4) . ?
O4B H41B 0.91(5) . ?
O4B H42B 0.88(4) . ?
O6B H61B 0.78(3) . ?
O6B H62B 0.83(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
O6A Na1A O1A 99.67(7) 1_655 . ?
O6A Na1A O4A 75.51(7) 1_655 . ?
O1A Na1A O4A 89.16(8) . . ?
O6A Na1A O11A 82.46(7) 1_655 2_666 ?
O1A Na1A O11A 81.00(7) . 2_666 ?
O4A Na1A O11A 154.00(7) . 2_666 ?
O6A Na1A O5A 84.32(6) 1_655 2_656 ?
O1A Na1A O5A 175.57(7) . 2_656 ?
O4A Na1A O5A 93.72(7) . 2_656 ?
O11A Na1A O5A 97.71(6) 2_666 2_656 ?
O6A Na1A O2A 172.23(7) 1_655 1_545 ?
O1A Na1A O2A 81.04(6) . 1_545 ?
O4A Na1A O2A 112.26(7) . 1_545 ?
O11A Na1A O2A 90.03(6) 2_666 1_545 ?
O5A Na1A O2A 94.74(6) 2_656 1_545 ?
O6A Na1A Na2A 41.46(5) 1_655 1_655 ?
O1A Na1A Na2A 141.07(5) . 1_655 ?
O4A Na1A Na2A 79.76(6) . 1_655 ?
O11A Na1A Na2A 92.86(5) 2_666 1_655 ?
O5A Na1A Na2A 43.03(4) 2_656 1_655 ?
O2A Na1A Na2A 137.67(4) 1_545 1_655 ?
O6A Na1A Na2A 138.19(5) 1_655 . ?
O1A Na1A Na2A 38.87(4) . . ?
O4A Na1A Na2A 102.57(6) . . ?
O11A Na1A Na2A 84.73(5) 2_666 . ?
O5A Na1A Na2A 136.93(5) 2_656 . ?
O2A Na1A Na2A 42.19(4) 1_545 . ?
Na2A Na1A Na2A 177.56(4) 1_655 . ?
O6A Na1A H12A 89.4(7) 1_655 . ?
O1A Na1A H12A 17.6(7) . . ?
O4A Na1A H12A 100.5(7) . . ?
O11A Na1A H12A 65.2(8) 2_666 . ?
O5A Na1A H12A 162.5(8) 2_656 . ?
O2A Na1A H12A 89.3(7) 1_545 . ?
Na2A Na1A H12A 129.8(7) 1_655 . ?
Na2A Na1A H12A 49.3(7) . . ?
O1A Na2A O42A 88.35(7) . . ?
O1A Na2A O3A 83.83(8) . . ?
O42A Na2A O3A 153.07(7) . . ?
O1A Na2A O6A 101.41(7) . . ?
O42A Na2A O6A 80.49(6) . . ?
O3A Na2A O6A 75.91(7) . . ?
O1A Na2A O2A 83.09(6) . 1_545 ?
O42A Na2A O2A 95.89(6) . 1_545 ?
O3A Na2A O2A 108.63(7) . 1_545 ?
O6A Na2A O2A 174.06(7) . 1_545 ?
O1A Na2A O5A 177.38(7) . 2_556 ?
O42A Na2A O5A 93.97(6) . 2_556 ?
O3A Na2A O5A 94.60(7) . 2_556 ?
O6A Na2A O5A 80.20(6) . 2_556 ?
O2A Na2A O5A 95.44(6) 1_545 2_556 ?
O1A Na2A Na1A 140.42(5) . 1_455 ?
O42A Na2A Na1A 88.96(5) . 1_455 ?
O3A Na2A Na1A 81.01(6) . 1_455 ?
O6A Na2A Na1A 39.36(4) . 1_455 ?
O2A Na2A Na1A 136.44(5) 1_545 1_455 ?
O5A Na2A Na1A 41.00(4) 2_556 1_455 ?
O1A Na2A Na1A 39.52(5) . . ?
O42A Na2A Na1A 93.46(5) . . ?
O3A Na2A Na1A 96.68(6) . . ?
O6A Na2A Na1A 140.88(5) . . ?
O2A Na2A Na1A 43.59(4) 1_545 . ?
O5A Na2A Na1A 138.93(5) 2_556 . ?
Na1A Na2A Na1A 177.56(4) 1_455 . ?
O1A Na2A H62A 93.5(7) . . ?
O42A Na2A H62A 64.2(8) . . ?
O3A Na2A H62A 90.6(8) . . ?
O6A Na2A H62A 17.7(8) . . ?
O2A Na2A H62A 159.9(8) 1_545 . ?
O5A Na2A H62A 88.6(7) 2_556 . ?
Na1A Na2A H62A 50.6(7) 1_455 . ?
Na1A Na2A H62A 130.5(7) . . ?
C2A O2A Na2A 131.92(13) . 1_565 ?
C2A O2A Na1A 116.73(13) . 1_565 ?
Na2A O2A Na1A 94.23(6) 1_565 1_565 ?
C2A O2A H2A 105(2) . . ?
Na2A O2A H2A 112(2) 1_565 . ?
Na1A O2A H2A 89(2) 1_565 . ?
C5A O5A Na1A 130.95(13) . 2_656 ?
C5A O5A Na2A 117.77(13) . 2_556 ?
Na1A O5A Na2A 95.97(6) 2_656 2_556 ?
C5A O5A H5A 103(2) . . ?
Na1A O5A H5A 110(2) 2_656 . ?
Na2A O5A H5A 93(2) 2_556 . ?
C11A O11A Na1A 129.06(13) . 2_666 ?
C41A O42A Na2A 127.91(13) . . ?
C6A C1A C2A 119.18(18) . . ?
C6A C1A C11A 120.85(17) . . ?
C2A C1A C11A 119.96(17) . . ?
O2A C2A C3A 119.03(17) . . ?
O2A C2A C1A 121.16(18) . . ?
C3A C2A C1A 119.81(18) . . ?
C2A C3A C4A 120.93(18) . . ?
C2A C3A H3A 119.5 . . ?
C4A C3A H3A 119.5 . . ?
C3A C4A C5A 119.05(18) . . ?
C3A C4A C41A 120.67(17) . . ?
C5A C4A C41A 120.28(17) . . ?
O5A C5A C6A 119.58(17) . . ?
O5A C5A C4A 120.28(17) . . ?
C6A C5A C4A 120.15(18) . . ?
C5A C6A C1A 120.87(18) . . ?
C5A C6A H6A 119.6 . . ?
C1A C6A H6A 119.6 . . ?
O12A C11A O11A 123.26(19) . . ?
O12A C11A C1A 119.45(18) . . ?
O11A C11A C1A 117.29(17) . . ?
O41A C41A O42A 123.24(19) . . ?
O41A C41A C4A 119.56(18) . . ?
O42A C41A C4A 117.20(18) . . ?
Na2A O1A Na1A 101.62(7) . . ?
Na2A O1A H11A 118(2) . . ?
Na1A O1A H11A 118(2) . . ?
Na2A O1A H12A 116(2) . . ?
Na1A O1A H12A 97(2) . . ?
H11A O1A H12A 105(3) . . ?
Na2A O3A H31A 105(2) . . ?
Na2A O3A H32A 98(3) . . ?
H31A O3A H32A 109(3) . . ?
Na1A O4A H41A 128(2) . . ?
Na1A O4A H42A 108(2) . . ?
H41A O4A H42A 108(3) . . ?
Na1A O6A Na2A 99.19(7) 1_455 . ?
Na1A O6A H61A 116(2) 1_455 . ?
Na2A O6A H61A 121(2) . . ?
Na1A O6A H62A 121(2) 1_455 . ?
Na2A O6A H62A 92(2) . . ?
H61A O6A H62A 106(3) . . ?
O1B Na1B O11B 87.44(7) . 2_667 ?
O1B Na1B O4B 83.70(8) . . ?
O11B Na1B O4B 151.34(7) 2_667 . ?
O1B Na1B O6B 101.33(7) . 1_655 ?
O11B Na1B O6B 79.29(6) 2_667 1_655 ?
O4B Na1B O6B 75.85(7) . 1_655 ?
O1B Na1B O2B 82.83(6) . 1_545 ?
O11B Na1B O2B 99.42(6) 2_667 1_545 ?
O4B Na1B O2B 106.40(7) . 1_545 ?
O6B Na1B O2B 175.53(7) 1_655 1_545 ?
O1B Na1B O5B 177.56(7) . 2_657 ?
O11B Na1B O5B 93.37(6) 2_667 2_657 ?
O4B Na1B O5B 96.63(7) . 2_657 ?
O6B Na1B O5B 81.08(6) 1_655 2_657 ?
O2B Na1B O5B 94.76(6) 1_545 2_657 ?
O1B Na1B Na2B 141.10(5) . 1_655 ?
O11B Na1B Na2B 89.07(5) 2_667 1_655 ?
O4B Na1B Na2B 81.09(6) . 1_655 ?
O6B Na1B Na2B 40.15(4) 1_655 1_655 ?
O2B Na1B Na2B 135.86(5) 1_545 1_655 ?
O5B Na1B Na2B 41.26(4) 2_657 1_655 ?
O1B Na1B Na2B 38.91(5) . . ?
O11B Na1B Na2B 93.82(5) 2_667 . ?
O4B Na1B Na2B 96.17(6) . . ?
O6B Na1B Na2B 140.20(5) 1_655 . ?
O2B Na1B Na2B 43.93(4) 1_545 . ?
O5B Na1B Na2B 138.69(4) 2_657 . ?
Na2B Na1B Na2B 177.09(3) 1_655 . ?
O6B Na2B O3B 75.97(7) . . ?
O6B Na2B O1B 99.91(7) . . ?
O3B Na2B O1B 89.85(8) . . ?
O6B Na2B O42B 83.29(7) . . ?
O3B Na2B O42B 156.14(7) . . ?
O1B Na2B O42B 82.13(7) . . ?
O6B Na2B O5B 84.47(6) . 2_557 ?
O3B Na2B O5B 95.57(7) . 2_557 ?
O1B Na2B O5B 173.75(7) . 2_557 ?
O42B Na2B O5B 94.02(6) . 2_557 ?
O6B Na2B O2B 173.83(7) . 1_545 ?
O3B Na2B O2B 110.19(7) . 1_545 ?
O1B Na2B O2B 80.06(6) . 1_545 ?
O42B Na2B O2B 90.60(6) . 1_545 ?
O5B Na2B O2B 95.11(6) 2_557 1_545 ?
O6B Na2B Na1B 42.03(4) . 1_455 ?
O3B Na2B Na1B 80.13(6) . 1_455 ?
O1B Na2B Na1B 141.91(5) . 1_455 ?
O42B Na2B Na1B 92.39(5) . 1_455 ?
O5B Na2B Na1B 42.79(4) 2_557 1_455 ?
O2B Na2B Na1B 137.90(4) 1_545 1_455 ?
O6B Na2B Na1B 137.45(5) . . ?
O3B Na2B Na1B 102.63(6) . . ?
O1B Na2B Na1B 37.90(4) . . ?
O42B Na2B Na1B 84.71(5) . . ?
O5B Na2B Na1B 137.10(5) 2_557 . ?
O2B Na2B Na1B 42.16(4) 1_545 . ?
Na1B Na2B Na1B 177.09(4) 1_455 . ?
O6B Na2B H12B 90.6(8) . . ?
O3B Na2B H12B 101.8(8) . . ?
O1B Na2B H12B 17.3(8) . . ?
O42B Na2B H12B 66.3(8) . . ?
O5B Na2B H12B 160.2(8) 2_557 . ?
O2B Na2B H12B 87.7(7) 1_545 . ?
Na1B Na2B H12B 131.4(8) 1_455 . ?
Na1B Na2B H12B 47.4(8) . . ?
C2B O2B Na1B 133.28(13) . 1_565 ?
C2B O2B Na2B 117.80(13) . 1_565 ?
Na1B O2B Na2B 93.92(5) 1_565 1_565 ?
C2B O2B H2B 103(2) . . ?
Na1B O2B H2B 108(2) 1_565 . ?
Na2B O2B H2B 94(2) 1_565 . ?
C5B O5B Na2B 129.53(13) . 2_557 ?
C5B O5B Na1B 116.68(13) . 2_657 ?
Na2B O5B Na1B 95.95(6) 2_557 2_657 ?
C5B O5B H5B 104(2) . . ?
Na2B O5B H5B 113(2) 2_557 . ?
Na1B O5B H5B 91(2) 2_657 . ?
C11B O11B Na1B 130.23(14) . 2_667 ?
C41B O42B Na2B 126.83(13) . . ?
C6B C1B C2B 119.19(18) . . ?
C6B C1B C11B 120.48(17) . . ?
C2B C1B C11B 120.33(17) . . ?
O2B C2B C3B 119.23(17) . . ?
O2B C2B C1B 120.81(18) . . ?
C3B C2B C1B 119.95(18) . . ?
C2B C3B C4B 121.00(18) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B H3B 119.5 . . ?
C3B C4B C5B 118.92(18) . . ?
C3B C4B C41B 121.25(17) . . ?
C5B C4B C41B 119.83(17) . . ?
O5B C5B C6B 119.16(17) . . ?
O5B C5B C4B 120.74(18) . . ?
C6B C5B C4B 120.10(17) . . ?
C5B C6B C1B 120.83(18) . . ?
C5B C6B H6B 119.6 . . ?
C1B C6B H6B 119.6 . . ?
O12B C11B O11B 123.83(19) . . ?
O12B C11B C1B 118.97(17) . . ?
O11B C11B C1B 117.19(18) . . ?
O41B C41B O42B 123.15(19) . . ?
O41B C41B C4B 119.68(18) . . ?
O42B C41B C4B 117.16(17) . . ?
Na1B O1B Na2B 103.19(7) . . ?
Na1B O1B H11B 111(2) . . ?
Na2B O1B H11B 125(2) . . ?
Na1B O1B H12B 112(2) . . ?
Na2B O1B H12B 97(2) . . ?
H11B O1B H12B 107(3) . . ?
Na2B O3B H31B 130(2) . . ?
Na2B O3B H32B 111(2) . . ?
H31B O3B H32B 102(3) . . ?
Na1B O4B H41B 101(3) . . ?
Na1B O4B H42B 106(2) . . ?
H41B O4B H42B 112(3) . . ?
Na2B O6B Na1B 97.82(7) . 1_455 ?
Na2B O6B H61B 118(2) . . ?
Na1B O6B H61B 118(2) 1_455 . ?
Na2B O6B H62B 122(2) . . ?
Na1B O6B H62B 96(2) 1_455 . ?
H61B O6B H62B 103(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
O2A H2A O11A 0.84(4) 1.71(3) 2.487(2) 155(3) . yes
O5A H5A O42A 0.89(4) 1.64(4) 2.476(2) 156(3) . yes
O1A H11A O12B 0.79(3) 2.12(3) 2.852(2) 156(3) 1_544 yes
O3A H31A O12B 0.93(4) 1.92(4) 2.826(3) 166(3) 1_544 yes
O3A H32A O4A 0.88(4) 1.98(4) 2.856(3) 177(4) 1_455 yes
O4A H41A O4B 0.90(4) 1.79(4) 2.692(2) 177(4) 2_646 yes
O4A H42A O41B 0.87(4) 1.93(4) 2.722(2) 151(3) 2_656 yes
O6A H61A O41B 0.77(3) 2.21(3) 2.933(2) 155(3) 2_556 yes
O6A H62A O41A 0.79(3) 1.95(4) 2.730(2) 169(3) . yes
O2B H2B O11B 0.84(3) 1.70(3) 2.492(2) 156(3) . yes
O5B H5B O42B 0.84(4) 1.68(3) 2.469(2) 156(3) . yes
O1B H11B O12A 0.77(3) 2.09(3) 2.840(2) 165(3) 1_545 yes
O3B H31B O3A 0.93(4) 1.76(4) 2.687(3) 174(4) 2_546 yes
O3B H32B O41A 0.87(4) 1.93(4) 2.710(2) 149(3) 2_556 yes
O4B H41B O3B 0.91(5) 1.95(5) 2.852(3) 174(4) 1_655 yes
O4B H42B O12A 0.88(4) 1.98(4) 2.841(3) 166(4) 1_545 yes
O6B H61B O41A 0.78(3) 2.25(3) 2.956(2) 152(3) 2_556 yes
O6B H62B O11B 0.83(4) 2.65(4) 3.097(2) 115(3) 2_567 yes
O6B H62B O12B 0.83(4) 1.94(4) 2.756(2) 168(3) 2_567 yes

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.079


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
