# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1835693'
loop_
_audit_author_name
_audit_author_address
'Xiaoqiang Liang'
;X
China
;
_audit_update_record             
;
2019-05-20 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-05-01
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2019.03.18 svn.r3573 for OlexSys, GUI svn.r5585)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H5 O8), 2(H2 O), C5 H14 N2'
_chemical_formula_sum            'C25 H28 N2 O18'
_chemical_formula_weight         644.49
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5370(12)
_cell_length_b                   8.7025(12)
_cell_length_c                   9.7295(18)
_cell_angle_alpha                84.792(3)
_cell_angle_beta                 88.545(2)
_cell_angle_gamma                68.948(2)
_cell_volume                     671.79(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1696
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_preparation       
'Dielectric Response and Proton Conduction,Dielectric Property and Proton Conduction'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4326
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.102
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2274
_reflns_number_total             2762
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXTL (Bruker, 2008)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All O(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1W-H1WA = O1W-H1WB
 0.85 with sigma of 0.02
 H1WA-H1WB
 1.34 with sigma of 0.04
 N14-C11 \\sim C13-C11 \\sim C15-N12
 with sigma of 0.01
 C14-N12 \\sim C14-C13 \\sim C12-C15 \\sim C12-N14
 with sigma of 0.01
 C15-C11 \\sim C11-N12
 with sigma of 0.01
3. Rigid body (RIGU) restrains
 N14, N12, C14, C15, C13, C12, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: N12(0.5) H12A(0.5) H12B(0.5) C14(0.5) H14A(0.5) H14B(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) C11(0.5) H11A(0.5) H11B(0.5) N14(0.5) H14C(0.5) H14D(0.5)
 C12(0.5) H12C(0.5) H12D(0.5) C15(0.5) H15A(0.5) H15B(0.5)
5.a Riding coordinates:
 O2(H2), O4(H4A), O7(H7)
5.b Secondary CH2 refined with riding coordinates:
 N12(H12A,H12B), C14(H14A,H14B), C13(H13A,H13B), C11(H11A,H11B), N14(H14C,
 H14D), C12(H12C,H12D), C15(H15A,H15B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C1 C 0.41949(17) 0.33983(18) 0.09459(14) 0.0268(3) Uani 1 1 d . . . . .
H1 H 0.497699 0.275901 0.161194 0.032 Uiso 1 1 calc R . . . .
C2 C 0.43776(16) 0.29402(18) -0.04098(14) 0.0264(3) Uani 1 1 d . . . . .
C3 C 0.32234(16) 0.39077(18) -0.14168(14) 0.0252(3) Uani 1 1 d . . . . .
C4 C 0.19270(17) 0.53033(19) -0.10340(14) 0.0277(3) Uani 1 1 d . . . . .
H4 H 0.116962 0.596648 -0.170717 0.033 Uiso 1 1 calc R . . . .
C5 C 0.17179(17) 0.57464(18) 0.03135(14) 0.0257(3) Uani 1 1 d . . . . .
C6 C 0.28820(16) 0.47772(18) 0.13238(14) 0.0258(3) Uani 1 1 d . . . . .
C7 C 0.28130(17) 0.52232(19) 0.28065(14) 0.0274(3) Uani 1 1 d . . . . .
C8 C 0.58727(18) 0.13747(19) -0.05962(15) 0.0316(4) Uani 1 1 d . . . . .
C9 C 0.31802(18) 0.3611(2) -0.29337(15) 0.0314(3) Uani 1 1 d . . . . .
C10 C 0.02761(17) 0.7236(2) 0.06923(15) 0.0295(3) Uani 1 1 d . . . . .
O1 O 0.33978(14) 0.62030(16) 0.31564(11) 0.0426(3) Uani 1 1 d . . . . .
O2 O 0.21282(14) 0.43824(15) 0.36362(10) 0.0391(3) Uani 1 1 d . . . . .
H2 H 0.210560 0.466503 0.445216 0.047 Uiso 1 1 d R . . . .
O3 O 0.70321(12) 0.08915(14) 0.02735(11) 0.0422(3) Uani 1 1 d . . . . .
O4 O 0.59248(13) 0.05105(14) -0.16190(11) 0.0392(3) Uani 1 1 d . . . . .
H4A H 0.508443 0.020337 -0.156463 0.047 Uiso 1 1 d R . . . .
O5 O 0.37993(14) 0.21712(15) -0.33178(11) 0.0411(3) Uani 1 1 d . . . . .
O6 O 0.24501(14) 0.48320(15) -0.37574(10) 0.0405(3) Uani 1 1 d . . . . .
O7 O -0.05750(13) 0.81662(15) -0.03650(11) 0.0446(3) Uani 1 1 d . . . . .
H7 H -0.136887 0.899374 -0.009286 0.054 Uiso 1 1 d R . . . .
O8 O -0.00311(14) 0.75425(15) 0.18719(11) 0.0474(3) Uani 1 1 d . . . . .
O1W O 0.59994(19) 0.2417(2) -0.57368(18) 0.0730(5) Uani 1 1 d D . . . .
H1WA H 0.524(3) 0.213(4) -0.522(3) 0.110 Uiso 1 1 d DR . . . .
H1WB H 0.548(3) 0.344(2) -0.609(3) 0.110 Uiso 1 1 d DR . . . .
N12 N 0.1028(12) 1.0160(13) -0.3791(9) 0.0437(15) Uani 0.5 1 d D U P A -1
H12A H 0.201694 0.935199 -0.386782 0.052 Uiso 0.5 1 calc R . P A -1
H12B H 0.104694 1.060977 -0.300912 0.052 Uiso 0.5 1 calc R . P A -1
C14 C 0.0830(12) 1.1416(10) -0.4944(6) 0.0575(19) Uani 0.5 1 d D U P A -1
H14A H 0.172099 1.185189 -0.487632 0.069 Uiso 0.5 1 calc R . P A -1
H14B H -0.022264 1.231683 -0.482301 0.069 Uiso 0.5 1 calc R . P A -1
C13 C 0.0843(7) 1.0925(7) -0.6345(6) 0.0561(12) Uani 0.5 1 d D U P A -1
H13A H 0.159892 0.978791 -0.637000 0.067 Uiso 0.5 1 calc R . P A -1
H13B H 0.127421 1.160955 -0.697021 0.067 Uiso 0.5 1 calc R . P A -1
C11 C -0.0849(6) 1.1073(6) -0.6841(4) 0.0611(11) Uani 0.5 1 d D U P A -1
H11A H -0.083248 1.104038 -0.783509 0.073 Uiso 0.5 1 calc R . P A -1
H11B H -0.166881 1.212662 -0.662442 0.073 Uiso 0.5 1 calc R . P A -1
N14 N -0.1350(13) 0.9695(13) -0.6175(10) 0.0421(13) Uani 0.5 1 d D U P A -1
H14C H -0.242022 1.013752 -0.593183 0.050 Uiso 0.5 1 calc R . P A -1
H14D H -0.130746 0.902132 -0.682175 0.050 Uiso 0.5 1 calc R . P A -1
C12 C -0.0412(11) 0.8653(9) -0.4952(7) 0.0559(17) Uani 0.5 1 d D U P A -1
H12C H -0.092351 0.784023 -0.468700 0.067 Uiso 0.5 1 calc R . P A -1
H12D H 0.072077 0.805200 -0.524737 0.067 Uiso 0.5 1 calc R . P A -1
C15 C -0.0278(8) 0.9439(8) -0.3695(5) 0.0605(13) Uani 0.5 1 d D U P A -1
H15A H -0.134850 1.029830 -0.353510 0.073 Uiso 0.5 1 calc R . P A -1
H15B H -0.003940 0.861838 -0.290839 0.073 Uiso 0.5 1 calc R . P A -1


_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
C1 H1 0.9300 . ?
C1 C2 1.4012(19) . ?
C1 C6 1.387(2) . ?
C2 C3 1.3939(19) . ?
C2 C8 1.517(2) . ?
C3 C4 1.391(2) . ?
C3 C9 1.525(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.3892(19) . ?
C5 C6 1.4008(19) . ?
C5 C10 1.499(2) . ?
C6 C7 1.522(2) . ?
C7 O1 1.2081(18) . ?
C7 O2 1.3057(18) . ?
C8 O3 1.2456(17) . ?
C8 O4 1.2913(19) . ?
C9 O5 1.2605(19) . ?
C9 O6 1.2466(18) . ?
C10 O7 1.3061(17) . ?
C10 O8 1.2030(18) . ?
O2 H2 0.8500 . ?
O4 H4A 0.8498 . ?
O7 H7 0.8502 . ?
O1W H1WA 0.903(17) . ?
O1W H1WB 0.879(17) . ?
N12 H12A 0.8900 . ?
N12 H12B 0.8900 . ?
N12 C14 1.461(6) . ?
N12 C15 1.461(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.464(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C11 1.492(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N14 1.501(5) . ?
N14 H14C 0.8900 . ?
N14 H14D 0.8900 . ?
N14 C12 1.487(6) . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C12 C15 1.481(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C6 C1 C2 121.94(13) . . ?
C1 C2 C8 113.52(12) . . ?
C3 C2 C1 119.27(13) . . ?
C3 C2 C8 127.20(13) . . ?
C2 C3 C9 127.48(13) . . ?
C4 C3 C2 118.41(13) . . ?
C4 C3 C9 114.10(12) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.64(13) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C6 118.90(13) . . ?
C4 C5 C10 121.03(12) . . ?
C6 C5 C10 120.08(12) . . ?
C1 C6 C5 118.81(13) . . ?
C1 C6 C7 118.55(12) . . ?
C5 C6 C7 122.57(13) . . ?
O1 C7 C6 122.42(13) . . ?
O1 C7 O2 125.06(13) . . ?
O2 C7 C6 112.45(13) . . ?
O3 C8 C2 119.51(14) . . ?
O3 C8 O4 119.82(14) . . ?
O4 C8 C2 120.63(13) . . ?
O5 C9 C3 120.66(13) . . ?
O6 C9 C3 117.45(14) . . ?
O6 C9 O5 121.82(13) . . ?
O7 C10 C5 114.11(12) . . ?
O8 C10 C5 122.05(13) . . ?
O8 C10 O7 123.82(14) . . ?
C7 O2 H2 110.0 . . ?
C8 O4 H4A 108.3 . . ?
C10 O7 H7 110.2 . . ?
H1WA O1W H1WB 107(2) . . ?
H12A N12 H12B 107.5 . . ?
C14 N12 H12A 108.5 . . ?
C14 N12 H12B 108.5 . . ?
C15 N12 H12A 108.5 . . ?
C15 N12 H12B 108.5 . . ?
C15 N12 C14 114.9(6) . . ?
N12 C14 H14A 107.8 . . ?
N12 C14 H14B 107.8 . . ?
N12 C14 C13 118.0(8) . . ?
H14A C14 H14B 107.2 . . ?
C13 C14 H14A 107.8 . . ?
C13 C14 H14B 107.8 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C14 C13 C11 113.2(5) . . ?
H13A C13 H13B 107.7 . . ?
C11 C13 H13A 108.9 . . ?
C11 C13 H13B 108.9 . . ?
C13 C11 H11A 109.5 . . ?
C13 C11 H11B 109.5 . . ?
C13 C11 N14 110.8(5) . . ?
H11A C11 H11B 108.1 . . ?
N14 C11 H11A 109.5 . . ?
N14 C11 H11B 109.5 . . ?
C11 N14 H14C 107.2 . . ?
C11 N14 H14D 107.2 . . ?
H14C N14 H14D 106.9 . . ?
C12 N14 C11 120.4(6) . . ?
C12 N14 H14C 107.2 . . ?
C12 N14 H14D 107.2 . . ?
N14 C12 H12C 107.4 . . ?
N14 C12 H12D 107.4 . . ?
H12C C12 H12D 107.0 . . ?
C15 C12 N14 119.6(7) . . ?
C15 C12 H12C 107.4 . . ?
C15 C12 H12D 107.4 . . ?
N12 C15 C12 112.8(7) . . ?
N12 C15 H15A 109.0 . . ?
N12 C15 H15B 109.0 . . ?
C12 C15 H15A 109.0 . . ?
C12 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?

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
O2 H2 O6 0.85 1.80 2.6368(15) 167.1 1_556 yes
O4 H4A O3 0.85 2.58 3.3660(17) 154.3 2_655 yes
O7 H7 O3 0.85 1.78 2.6279(15) 171.9 1_465 yes
O7 H7 O4 0.85 2.63 3.1517(15) 120.9 1_465 yes
O1W H1WA O5 0.903(17) 2.19(2) 3.014(2) 151(3) . yes
N12 H12A O1W 0.89 1.89 2.778(13) 172.0 2_664 yes
N12 H12B O8 0.89 1.96 2.754(13) 148.1 2_575 yes
C11 H11A O7 0.97 2.29 3.064(4) 135.9 2_574 yes
C11 H11B O1W 0.97 2.09 2.753(5) 124.2 1_465 yes
N14 H14C O1W 0.89 1.98 2.683(13) 134.7 1_465 yes
N14 H14D O8 0.89 1.92 2.722(14) 149.5 1_554 yes

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 C9 -178.87(14) . . . . ?
C1 C2 C8 O3 -19.5(2) . . . . ?
C1 C2 C8 O4 157.99(14) . . . . ?
C1 C6 C7 O1 94.24(18) . . . . ?
C1 C6 C7 O2 -83.01(16) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C6 C7 -177.77(13) . . . . ?
C2 C3 C4 C5 -1.5(2) . . . . ?
C2 C3 C9 O5 26.6(2) . . . . ?
C2 C3 C9 O6 -156.43(15) . . . . ?
C3 C2 C8 O3 160.84(15) . . . . ?
C3 C2 C8 O4 -21.6(2) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C3 C4 C5 C10 -178.31(14) . . . . ?
C4 C3 C9 O5 -152.45(14) . . . . ?
C4 C3 C9 O6 24.54(19) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 176.33(13) . . . . ?
C4 C5 C10 O7 -9.4(2) . . . . ?
C4 C5 C10 O8 171.95(15) . . . . ?
C5 C6 C7 O1 -82.72(19) . . . . ?
C5 C6 C7 O2 100.04(16) . . . . ?
C6 C1 C2 C3 1.0(2) . . . . ?
C6 C1 C2 C8 -178.71(13) . . . . ?
C6 C5 C10 O7 170.57(13) . . . . ?
C6 C5 C10 O8 -8.1(2) . . . . ?
C8 C2 C3 C4 179.74(14) . . . . ?
C8 C2 C3 C9 0.7(3) . . . . ?
C9 C3 C4 C5 177.64(13) . . . . ?
C10 C5 C6 C1 179.44(13) . . . . ?
C10 C5 C6 C7 -3.6(2) . . . . ?
N12 C14 C13 C11 87.7(9) . . . . ?
C14 N12 C15 C12 58.3(13) . . . . ?
C14 C13 C11 N14 -75.2(8) . . . . ?
C13 C11 N14 C12 13.9(12) . . . . ?
C11 N14 C12 C15 57.8(14) . . . . ?
N14 C12 C15 N12 -80.8(8) . . . . ?
C15 N12 C14 C13 -61.0(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 1835694'
loop_
_audit_author_name
_audit_author_address
'Xiaoqiang liang'
;Xi?an, 710048
China
;
_audit_update_record             
;
2018-04-09 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H5 O8), C5 H14 N2, H2 O'
_chemical_formula_sum            'C25 H26 N2 O17'
_chemical_formula_weight         626.48

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'
N N 0.0061 0.0033 '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'

_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                   9.6090(18)
_cell_length_b                   9.757(2)
_cell_length_c                   15.7080(12)
_cell_angle_alpha                71.915(2)
_cell_angle_beta                 76.613(3)
_cell_angle_gamma                87.499(2)
_cell_volume                     1361.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4285
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.12

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10022
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_av_R_equivalents  0.0082
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.401
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6630
_reflns_number_gt                4207
_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       'SMART (Bruker, 2008)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_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)+(0.0150P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6630
_refine_ls_number_parameters     398
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.015
_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
C1 C 0.49757(17) 0.96304(17) 0.63040(10) 0.0415(4) Uani 1 1 d . . . . .
C2 C 0.59859(17) 0.85344(17) 0.63762(10) 0.0404(3) Uani 1 1 d . . . . .
C3 C 0.73207(17) 0.87915(18) 0.64880(10) 0.0421(4) Uani 1 1 d . . . . .
H3 H 0.798597 0.806617 0.653526 0.051 Uiso 1 1 calc R U . . .
C4 C 0.76804(16) 1.01440(18) 0.65308(10) 0.0408(3) Uani 1 1 d . . . . .
C5 C 0.66915(17) 1.12227(17) 0.64619(10) 0.0394(3) Uani 1 1 d . . . . .
C6 C 0.53436(16) 1.09632(17) 0.63480(10) 0.0395(3) Uani 1 1 d . . . . .
H6 H 0.468136 1.169134 0.630086 0.047 Uiso 1 1 calc R U . . .
C7 C 0.35058(16) 0.96141(19) 0.61303(10) 0.0426(4) Uani 1 1 d . U . . .
C8 C 0.58085(17) 0.70761(17) 0.62656(10) 0.0412(3) Uani 1 1 d . . . . .
C9 C 0.91302(17) 1.03133(18) 0.67094(10) 0.0429(4) Uani 1 1 d . . . . .
C10 C 0.70359(16) 1.26970(18) 0.64834(11) 0.0427(4) Uani 1 1 d . . . . .
C11 C 0.43430(18) 0.71566(18) 0.87510(11) 0.0447(4) Uani 1 1 d . . . . .
C12 C 0.53579(19) 0.60769(18) 0.88216(11) 0.0456(4) Uani 1 1 d . . . . .
C13 C 0.66934(19) 0.63387(18) 0.89646(11) 0.0456(4) Uani 1 1 d . . . . .
H13 H 0.736435 0.561886 0.901707 0.055 Uiso 1 1 calc R U . . .
C14 C 0.70187(19) 0.76733(19) 0.90283(11) 0.0469(4) Uani 1 1 d . . . . .
C15 C 0.60271(18) 0.87565(18) 0.89504(10) 0.0441(4) Uani 1 1 d . . . . .
C16 C 0.46950(18) 0.84898(18) 0.88133(11) 0.0452(4) Uani 1 1 d . . . . .
H16 H 0.402827 0.921376 0.876248 0.054 Uiso 1 1 calc R U . . .
C17 C 0.28813(19) 0.69119(19) 0.86310(11) 0.0463(4) Uani 1 1 d . . . . .
C18 C 0.50228(19) 0.46255(18) 0.87673(11) 0.0444(4) Uani 1 1 d . . . . .
C19 C 0.85080(18) 0.77653(19) 0.91903(11) 0.0474(4) Uani 1 1 d . . . . .
C20 C 0.63405(19) 1.02323(17) 0.89826(11) 0.0459(4) Uani 1 1 d . U . . .
C21 C 0.22357(19) 0.4480(2) 0.56795(11) 0.0533(4) Uani 1 1 d . . . . .
H21A H 0.152589 0.488791 0.533958 0.080 Uiso 1 1 calc R U . . .
H21B H 0.268552 0.370751 0.547097 0.080 Uiso 1 1 calc R U . . .
H21C H 0.294343 0.521020 0.558459 0.080 Uiso 1 1 calc R U . . .
C22 C 0.15392(19) 0.3912(2) 0.66801(11) 0.0555(5) Uani 1 1 d . . . . .
H22 H 0.131010 0.288850 0.680672 0.067 Uiso 1 1 calc R U . . .
C23 C 0.26122(19) 0.3969(2) 0.72097(12) 0.0525(4) Uani 1 1 d . . . . .
H23A H 0.280015 0.495523 0.717639 0.063 Uiso 1 1 calc R U . . .
H23B H 0.350360 0.356132 0.697720 0.063 Uiso 1 1 calc R U . . .
C24 C 0.05537(19) 0.3654(2) 0.85433(12) 0.0554(5) Uani 1 1 d . . . . .
H24A H 0.068953 0.461701 0.857162 0.067 Uiso 1 1 calc R U . . .
H24B H 0.012872 0.303626 0.915834 0.067 Uiso 1 1 calc R U . . .
C25 C -0.03987(18) 0.3688(2) 0.79074(12) 0.0515(4) Uani 1 1 d . . . . .
H25A H -0.131429 0.405828 0.813681 0.062 Uiso 1 1 calc R U . . .
H25B H -0.056792 0.270626 0.792329 0.062 Uiso 1 1 calc R U . . .
N1 N 0.19467(16) 0.30871(16) 0.81784(9) 0.0490(3) Uani 1 1 d . . . . .
H1A H 0.255130 0.308824 0.853853 0.059 Uiso 1 1 d R U . . .
H1B H 0.181650 0.216894 0.819812 0.059 Uiso 1 1 d R U . . .
N2 N 0.01805(15) 0.45986(17) 0.69030(9) 0.0518(4) Uani 1 1 d . . . . .
H2A H -0.039788 0.453726 0.654732 0.062 Uiso 1 1 calc R U . . .
H2B H 0.031191 0.552024 0.685285 0.062 Uiso 1 1 calc R U . . .
O1 O 0.26670(11) 1.06383(12) 0.62665(7) 0.0452(3) Uani 1 1 d . . . . .
H1C H 0.250489 1.111139 0.574682 0.054 Uiso 1 1 d R U . . .
O2 O 0.31746(12) 0.86480(12) 0.58218(7) 0.0437(3) Uani 1 1 d . U . . .
O3 O 0.47633(11) 0.67880(12) 0.59410(7) 0.0429(3) Uani 1 1 d . . . . .
H3A H 0.492989 0.597998 0.584421 0.052 Uiso 1 1 d R U . . .
O4 O 0.66131(12) 0.61193(13) 0.65610(7) 0.0455(3) Uani 1 1 d . . . . .
O5 O 1.01290(12) 1.06572(13) 0.59723(8) 0.0515(3) Uani 1 1 d . . . . .
O6 O 0.92472(12) 1.02051(13) 0.74944(8) 0.0479(3) Uani 1 1 d . . . . .
O7 O 0.59972(12) 1.35608(12) 0.65189(8) 0.0428(3) Uani 1 1 d . . . . .
H7A H 0.627902 1.426449 0.665366 0.051 Uiso 1 1 d R U . . .
O8 O 0.83265(11) 1.30483(12) 0.64429(8) 0.0451(3) Uani 1 1 d . . . . .
O9 O 0.27343(13) 0.72592(13) 0.78336(8) 0.0478(3) Uani 1 1 d . . . . .
O10 O 0.19687(13) 0.66510(14) 0.93794(8) 0.0497(3) Uani 1 1 d . . . . .
O11 O 0.38348(13) 0.42991(12) 0.87009(8) 0.0477(3) Uani 1 1 d . . . . .
O12 O 0.59698(12) 0.36365(13) 0.87832(8) 0.0469(3) Uani 1 1 d . . . . .
H12C H 0.586180 0.320148 0.840939 0.056 Uiso 1 1 d R U . . .
O13 O 0.93844(12) 0.68864(13) 0.89193(8) 0.0491(3) Uani 1 1 d . . . . .
H13A H 1.020947 0.710437 0.895793 0.059 Uiso 1 1 d R U . . .
O14 O 0.87826(12) 0.85428(13) 0.96212(7) 0.0475(3) Uani 1 1 d . . . . .
O15 O 0.54913(12) 1.11788(12) 0.86723(7) 0.0469(3) Uani 1 1 d . U . . .
O16 O 0.72916(12) 1.05423(13) 0.93616(8) 0.0485(3) Uani 1 1 d . U . . .
H16A H 0.732109 1.144787 0.926728 0.058 Uiso 1 1 d R U . . .
O1W O 0.15597(12) 0.01627(13) 0.84159(8) 0.0481(3) Uani 1 1 d . . . . .
H1WD H 0.129380 -0.055974 0.889280 0.058 Uiso 1 1 d R U . . .
H1WC H 0.138840 -0.007244 0.797170 0.058 Uiso 1 1 d R U . . .


_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
C1 C6 1.389(2) . ?
C1 C2 1.408(2) . ?
C1 C7 1.501(2) . ?
C2 C3 1.378(2) . ?
C2 C8 1.507(2) . ?
C3 C4 1.404(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(2) . ?
C4 C9 1.509(2) . ?
C5 C6 1.392(2) . ?
C5 C10 1.502(2) . ?
C6 H6 0.9300 . ?
C7 O2 1.267(2) . ?
C7 O1 1.2949(18) . ?
C8 O4 1.2323(19) . ?
C8 O3 1.3033(19) . ?
C9 O6 1.235(2) . ?
C9 O5 1.2831(17) . ?
C10 O7 1.2804(19) . ?
C10 O8 1.283(2) . ?
C11 C16 1.396(2) . ?
C11 C12 1.400(2) . ?
C11 C17 1.498(2) . ?
C12 C13 1.400(2) . ?
C12 C18 1.498(2) . ?
C13 C14 1.391(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(2) . ?
C14 C19 1.522(3) . ?
C15 C16 1.394(3) . ?
C15 C20 1.502(2) . ?
C16 H16 0.9300 . ?
C17 O9 1.232(2) . ?
C17 O10 1.254(2) . ?
C18 O11 1.234(2) . ?
C18 O12 1.296(2) . ?
C19 O14 1.234(2) . ?
C19 O13 1.2741(19) . ?
C20 O15 1.2630(19) . ?
C20 O16 1.292(2) . ?
C21 C22 1.493(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N2 1.461(2) . ?
C22 C23 1.480(3) . ?
C22 H22 0.9800 . ?
C23 N1 1.500(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N1 1.484(2) . ?
C24 C25 1.496(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N2 1.535(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
O1 H1C 0.8500 . ?
O3 H3A 0.8499 . ?
O7 H7A 0.8501 . ?
O12 H12C 0.8500 . ?
O13 H13A 0.8500 . ?
O16 H16A 0.8500 . ?
O1W H1WD 0.8500 . ?
O1W H1WC 0.8500 . ?

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
C6 C1 C2 119.18(15) . . ?
C6 C1 C7 111.82(14) . . ?
C2 C1 C7 128.92(16) . . ?
C3 C2 C1 120.03(15) . . ?
C3 C2 C8 113.77(14) . . ?
C1 C2 C8 126.01(15) . . ?
C2 C3 C4 120.26(15) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.93(15) . . ?
C5 C4 C9 122.91(15) . . ?
C3 C4 C9 117.06(14) . . ?
C4 C5 C6 119.80(15) . . ?
C4 C5 C10 121.92(15) . . ?
C6 C5 C10 118.27(14) . . ?
C1 C6 C5 120.81(14) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O2 C7 O1 123.60(15) . . ?
O2 C7 C1 118.79(14) . . ?
O1 C7 C1 117.53(15) . . ?
O4 C8 O3 120.33(14) . . ?
O4 C8 C2 117.95(14) . . ?
O3 C8 C2 121.46(14) . . ?
O6 C9 O5 126.71(15) . . ?
O6 C9 C4 120.23(13) . . ?
O5 C9 C4 112.90(14) . . ?
O7 C10 O8 123.29(15) . . ?
O7 C10 C5 116.67(14) . . ?
O8 C10 C5 120.01(14) . . ?
C16 C11 C12 118.96(17) . . ?
C16 C11 C17 119.10(15) . . ?
C12 C11 C17 121.93(16) . . ?
C13 C12 C11 119.92(16) . . ?
C13 C12 C18 119.25(14) . . ?
C11 C12 C18 120.82(17) . . ?
C14 C13 C12 120.13(16) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.48(17) . . ?
C15 C14 C19 126.44(17) . . ?
C13 C14 C19 113.08(15) . . ?
C14 C15 C16 119.26(16) . . ?
C14 C15 C20 122.66(16) . . ?
C16 C15 C20 118.06(15) . . ?
C15 C16 C11 121.25(15) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
O9 C17 O10 130.72(17) . . ?
O9 C17 C11 116.40(15) . . ?
O10 C17 C11 111.20(14) . . ?
O11 C18 O12 115.90(16) . . ?
O11 C18 C12 122.27(15) . . ?
O12 C18 C12 121.83(16) . . ?
O14 C19 O13 123.74(17) . . ?
O14 C19 C14 121.65(14) . . ?
O13 C19 C14 114.32(16) . . ?
O15 C20 O16 120.22(15) . . ?
O15 C20 C15 114.05(16) . . ?
O16 C20 C15 125.44(14) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C23 116.94(16) . . ?
N2 C22 C21 111.57(14) . . ?
C23 C22 C21 108.21(15) . . ?
N2 C22 H22 106.5 . . ?
C23 C22 H22 106.5 . . ?
C21 C22 H22 106.5 . . ?
C22 C23 N1 104.68(14) . . ?
C22 C23 H23A 110.8 . . ?
N1 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
N1 C23 H23B 110.8 . . ?
H23A C23 H23B 108.9 . . ?
N1 C24 C25 107.54(15) . . ?
N1 C24 H24A 110.2 . . ?
C25 C24 H24A 110.2 . . ?
N1 C24 H24B 110.2 . . ?
C25 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
C24 C25 N2 115.13(14) . . ?
C24 C25 H25A 108.5 . . ?
N2 C25 H25A 108.5 . . ?
C24 C25 H25B 108.5 . . ?
N2 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
C24 N1 C23 112.13(14) . . ?
C24 N1 H1A 109.2 . . ?
C23 N1 H1A 108.9 . . ?
C24 N1 H1B 109.3 . . ?
C23 N1 H1B 109.4 . . ?
H1A N1 H1B 107.9 . . ?
C22 N2 C25 100.99(13) . . ?
C22 N2 H2A 111.6 . . ?
C25 N2 H2A 111.6 . . ?
C22 N2 H2B 111.6 . . ?
C25 N2 H2B 111.6 . . ?
H2A N2 H2B 109.4 . . ?
C7 O1 H1C 106.4 . . ?
C8 O3 H3A 107.1 . . ?
C10 O7 H7A 107.2 . . ?
C18 O12 H12C 107.8 . . ?
C19 O13 H13A 107.6 . . ?
C20 O16 H16A 109.3 . . ?
H1WD O1W H1WC 106.0 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(2) . . . . ?
C7 C1 C2 C3 176.36(14) . . . . ?
C6 C1 C2 C8 -174.68(14) . . . . ?
C7 C1 C2 C8 1.8(3) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C8 C2 C3 C4 175.26(13) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C9 176.53(13) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C9 C4 C5 C6 -176.37(13) . . . . ?
C3 C4 C5 C10 -178.66(14) . . . . ?
C9 C4 C5 C10 5.1(2) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C7 C1 C6 C5 -177.00(13) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C10 C5 C6 C1 178.67(13) . . . . ?
C6 C1 C7 O2 160.56(14) . . . . ?
C2 C1 C7 O2 -16.1(2) . . . . ?
C6 C1 C7 O1 -16.32(19) . . . . ?
C2 C1 C7 O1 167.03(15) . . . . ?
C3 C2 C8 O4 22.3(2) . . . . ?
C1 C2 C8 O4 -162.84(14) . . . . ?
C3 C2 C8 O3 -163.55(13) . . . . ?
C1 C2 C8 O3 11.3(2) . . . . ?
C5 C4 C9 O6 78.0(2) . . . . ?
C3 C4 C9 O6 -98.33(19) . . . . ?
C5 C4 C9 O5 -97.83(18) . . . . ?
C3 C4 C9 O5 85.85(18) . . . . ?
C4 C5 C10 O7 -172.37(14) . . . . ?
C6 C5 C10 O7 9.1(2) . . . . ?
C4 C5 C10 O8 9.4(2) . . . . ?
C6 C5 C10 O8 -169.16(14) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
C17 C11 C12 C13 -177.82(14) . . . . ?
C16 C11 C12 C18 179.44(14) . . . . ?
C17 C11 C12 C18 0.8(2) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C18 C12 C13 C14 -179.21(13) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C19 179.60(14) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C19 C14 C15 C16 -179.18(15) . . . . ?
C13 C14 C15 C20 -177.92(14) . . . . ?
C19 C14 C15 C20 2.5(2) . . . . ?
C14 C15 C16 C11 -0.2(2) . . . . ?
C20 C15 C16 C11 178.26(13) . . . . ?
C12 C11 C16 C15 -0.5(2) . . . . ?
C17 C11 C16 C15 178.23(14) . . . . ?
C16 C11 C17 O9 88.19(19) . . . . ?
C12 C11 C17 O9 -93.2(2) . . . . ?
C16 C11 C17 O10 -78.64(19) . . . . ?
C12 C11 C17 O10 100.01(18) . . . . ?
C13 C12 C18 O11 175.30(15) . . . . ?
C11 C12 C18 O11 -3.3(2) . . . . ?
C13 C12 C18 O12 -5.0(2) . . . . ?
C11 C12 C18 O12 176.37(14) . . . . ?
C15 C14 C19 O14 29.7(3) . . . . ?
C13 C14 C19 O14 -149.92(16) . . . . ?
C15 C14 C19 O13 -156.28(15) . . . . ?
C13 C14 C19 O13 24.1(2) . . . . ?
C14 C15 C20 O15 162.82(14) . . . . ?
C16 C15 C20 O15 -15.5(2) . . . . ?
C14 C15 C20 O16 -23.4(2) . . . . ?
C16 C15 C20 O16 158.27(15) . . . . ?
N2 C22 C23 N1 65.47(19) . . . . ?
C21 C22 C23 N1 -167.57(15) . . . . ?
N1 C24 C25 N2 -58.1(2) . . . . ?
C25 C24 N1 C23 57.09(18) . . . . ?
C22 C23 N1 C24 -58.49(18) . . . . ?
C23 C22 N2 C25 -62.71(19) . . . . ?
C21 C22 N2 C25 172.00(17) . . . . ?
C24 C25 N2 C22 57.7(2) . . . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.048


_chemical_properties_physical    Deliquescent
_exptl_crystal_preparation       'Dielectric Response and Proton Conduction'
