# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_DT-Ce
_database_code_depnum_ccdc_archive 'CCDC 1944188'
loop_
_audit_author_name
_audit_author_address
'Miaoli Zhu'
;Shanxi University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 Ce N13 O11, 2(C H4 O)'
_chemical_formula_sum            'C24 H26 Ce N13 O13'
_chemical_formula_weight         844.70

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'
Ce Ce -0.2486 2.6331 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.8474(12)
_cell_length_b                   9.3378(5)
_cell_length_c                   18.2600(16)
_cell_angle_alpha                90
_cell_angle_beta                 126.4469(11)
_cell_angle_gamma                90
_cell_volume                     3270.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5264
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             1692
_exptl_transmission_factor_min   0.6523
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.476
_shelx_estimated_absorpt_T_min   0.626
_shelx_estimated_absorpt_T_max   0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker,2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12617
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.092
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3331
_reflns_number_gt                2717
_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       'Bruker APEX2 (Bruker, 2012)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2012)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2015a)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0041P)²+6.3085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3331
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
Ce1 Ce 0.000000 0.63434(3) 0.250000 0.02334(9) Uani 1 2 d S T P . .
N1 N 0.10786(13) 0.6455(3) 0.23316(18) 0.0283(6) Uani 1 1 d . . . . .
N2 N 0.00369(15) 0.4523(3) 0.13578(19) 0.0279(7) Uani 1 1 d . . . . .
N3 N -0.04528(16) 0.3446(3) 0.0944(2) 0.0325(8) Uani 1 1 d . . . . .
H3 H -0.0398(18) 0.278(4) 0.068(2) 0.041(12) Uiso 1 1 d . . . . .
N4 N -0.14571(15) 0.1394(4) 0.0113(2) 0.0425(8) Uani 1 1 d . . . . .
N5 N -0.22231(17) 0.0726(4) 0.0784(3) 0.0523(10) Uani 1 1 d . . . . .
N6 N 0.09509(17) 0.7198(3) 0.4543(2) 0.0360(8) Uani 1 1 d . . . . .
N7 N 0.000000 0.9640(5) 0.250000 0.0339(11) Uani 1 2 d S T P . .
O1 O -0.08227(12) 0.4096(2) 0.17825(16) 0.0321(6) Uani 1 1 d . . . . .
O2 O 0.11746(12) 0.6638(3) 0.41347(16) 0.0414(7) Uani 1 1 d . . . . .
O3 O 0.03182(13) 0.7567(3) 0.40648(17) 0.0409(7) Uani 1 1 d . . . . .
O4 O 0.13326(15) 0.7369(3) 0.53703(19) 0.0608(9) Uani 1 1 d . . . . .
O5 O 0.05523(11) 0.8932(3) 0.28208(17) 0.0376(7) Uani 1 1 d . . . . .
O6 O 0.000000 1.0950(4) 0.250000 0.0505(11) Uani 1 2 d S T P . .
C1 C 0.10455(18) 0.5657(4) 0.1688(2) 0.0307(9) Uani 1 1 d . . . . .
C2 C 0.1527(2) 0.5794(4) 0.1503(3) 0.0431(11) Uani 1 1 d . . . . .
H2 H 0.148918 0.523768 0.105353 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2065(2) 0.6770(5) 0.1995(3) 0.0521(12) Uani 1 1 d . . . . .
H3A H 0.239195 0.688754 0.187697 0.063 Uiso 1 1 calc R U . . .
C4 C 0.21081(19) 0.7556(5) 0.2657(3) 0.0458(11) Uani 1 1 d . . . . .
H4A H 0.247077 0.820280 0.300642 0.055 Uiso 1 1 calc R U . . .
C5 C 0.16061(18) 0.7376(4) 0.2799(3) 0.0358(9) Uani 1 1 d . . . . .
H5 H 0.163714 0.792784 0.324540 0.043 Uiso 1 1 calc R U . . .
C6 C 0.04966(18) 0.4589(4) 0.1214(2) 0.0314(9) Uani 1 1 d . . . . .
H6A H 0.048152 0.395876 0.080811 0.038 Uiso 1 1 calc R U . . .
C7 C -0.08616(18) 0.3291(3) 0.1222(2) 0.0280(8) Uani 1 1 d . . . . .
C8 C -0.13736(17) 0.2097(4) 0.0806(2) 0.0293(8) Uani 1 1 d . . . . .
C9 C -0.17536(19) 0.1768(4) 0.1129(3) 0.0406(10) Uani 1 1 d . . . . .
H9 H -0.167744 0.230130 0.161103 0.049 Uiso 1 1 calc R U . . .
C10 C -0.2305(2) 0.0028(5) 0.0096(3) 0.0543(12) Uani 1 1 d . . . . .
H10 H -0.263028 -0.070854 -0.017685 0.065 Uiso 1 1 calc R U . . .
C11 C -0.1928(2) 0.0345(5) -0.0233(3) 0.0544(12) Uani 1 1 d . . . . .
H11 H -0.200499 -0.019250 -0.071345 0.065 Uiso 1 1 calc R U . . .
O7 O 0.01882(19) 0.1361(4) 0.0529(3) 0.0758(10) Uani 1 1 d . . . . .
H7 H 0.021(5) 0.133(12) 0.006(7) 0.34(6) Uiso 1 1 d . . . . .
C12 C 0.0775(3) 0.0684(7) 0.1313(4) 0.096(2) Uani 1 1 d . . . . .
H12A H 0.115854 0.134463 0.162627 0.144 Uiso 1 1 calc R U . . .
H12B H 0.090442 -0.014044 0.113068 0.144 Uiso 1 1 calc R U . . .
H12C H 0.065837 0.039305 0.171167 0.144 Uiso 1 1 calc 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
Ce1 O2 2.626(2) . ?
Ce1 O2 2.626(2) 2 ?
Ce1 O1 2.630(2) . ?
Ce1 O1 2.630(2) 2 ?
Ce1 O5 2.646(2) 2 ?
Ce1 O5 2.646(2) . ?
Ce1 N2 2.732(3) . ?
Ce1 N2 2.732(3) 2 ?
Ce1 O3 2.733(3) . ?
Ce1 O3 2.733(3) 2 ?
Ce1 N1 2.768(2) . ?
Ce1 N1 2.768(2) 2 ?
N1 C5 1.332(4) . ?
N1 C1 1.353(4) . ?
N2 C6 1.272(4) . ?
N2 N3 1.377(4) . ?
N3 C7 1.348(4) . ?
N3 H3 0.84(4) . ?
N4 C8 1.332(4) . ?
N4 C11 1.333(5) . ?
N5 C10 1.322(5) . ?
N5 C9 1.327(4) . ?
N6 O4 1.226(4) . ?
N6 O2 1.260(3) . ?
N6 O3 1.262(4) . ?
N7 O6 1.223(5) . ?
N7 O5 1.264(3) 2 ?
N7 O5 1.264(3) . ?
O1 C7 1.227(4) . ?
C1 C2 1.382(4) . ?
C1 C6 1.453(5) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4A 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.487(5) . ?
C8 C9 1.378(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
O7 C12 1.424(6) . ?
O7 H7 0.89(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
O2 Ce1 O2 167.97(11) . 2 ?
O2 Ce1 O1 128.76(8) . . ?
O2 Ce1 O1 62.68(7) 2 . ?
O2 Ce1 O1 62.68(7) . 2 ?
O2 Ce1 O1 128.76(8) 2 2 ?
O1 Ce1 O1 74.11(10) . 2 ?
O2 Ce1 O5 102.15(8) . 2 ?
O2 Ce1 O5 66.31(8) 2 2 ?
O1 Ce1 O5 119.52(7) . 2 ?
O1 Ce1 O5 164.81(7) 2 2 ?
O2 Ce1 O5 66.31(8) . . ?
O2 Ce1 O5 102.15(8) 2 . ?
O1 Ce1 O5 164.81(7) . . ?
O1 Ce1 O5 119.52(7) 2 . ?
O5 Ce1 O5 48.06(10) 2 . ?
O2 Ce1 N2 115.88(8) . . ?
O2 Ce1 N2 72.18(8) 2 . ?
O1 Ce1 N2 58.40(8) . . ?
O1 Ce1 N2 62.03(8) 2 . ?
O5 Ce1 N2 129.55(8) 2 . ?
O5 Ce1 N2 119.98(8) . . ?
O2 Ce1 N2 72.18(8) . 2 ?
O2 Ce1 N2 115.88(8) 2 2 ?
O1 Ce1 N2 62.03(8) . 2 ?
O1 Ce1 N2 58.40(8) 2 2 ?
O5 Ce1 N2 119.98(8) 2 2 ?
O5 Ce1 N2 129.55(8) . 2 ?
N2 Ce1 N2 103.05(12) . 2 ?
O2 Ce1 O3 47.29(7) . . ?
O2 Ce1 O3 126.20(7) 2 . ?
O1 Ce1 O3 121.07(7) . . ?
O1 Ce1 O3 98.69(7) 2 . ?
O5 Ce1 O3 69.03(8) 2 . ?
O5 Ce1 O3 66.06(8) . . ?
N2 Ce1 O3 160.61(8) . . ?
N2 Ce1 O3 64.97(8) 2 . ?
O2 Ce1 O3 126.20(7) . 2 ?
O2 Ce1 O3 47.30(7) 2 2 ?
O1 Ce1 O3 98.70(7) . 2 ?
O1 Ce1 O3 121.07(7) 2 2 ?
O5 Ce1 O3 66.06(8) 2 2 ?
O5 Ce1 O3 69.03(8) . 2 ?
N2 Ce1 O3 64.97(8) . 2 ?
N2 Ce1 O3 160.61(8) 2 2 ?
O3 Ce1 O3 130.58(11) . 2 ?
O2 Ce1 N1 71.83(8) . . ?
O2 Ce1 N1 107.69(8) 2 . ?
O1 Ce1 N1 116.24(8) . . ?
O1 Ce1 N1 67.54(8) 2 . ?
O5 Ce1 N1 108.31(8) 2 . ?
O5 Ce1 N1 67.48(8) . . ?
N2 Ce1 N1 59.01(8) . . ?
N2 Ce1 N1 124.17(8) 2 . ?
O3 Ce1 N1 113.66(8) . . ?
O3 Ce1 N1 64.36(8) 2 . ?
O2 Ce1 N1 107.69(8) . 2 ?
O2 Ce1 N1 71.83(8) 2 2 ?
O1 Ce1 N1 67.54(8) . 2 ?
O1 Ce1 N1 116.24(8) 2 2 ?
O5 Ce1 N1 67.48(8) 2 2 ?
O5 Ce1 N1 108.31(8) . 2 ?
N2 Ce1 N1 124.17(8) . 2 ?
N2 Ce1 N1 59.01(8) 2 2 ?
O3 Ce1 N1 64.36(8) . 2 ?
O3 Ce1 N1 113.66(8) 2 2 ?
N1 Ce1 N1 175.68(13) . 2 ?
C5 N1 C1 117.2(3) . . ?
C5 N1 Ce1 122.7(2) . . ?
C1 N1 Ce1 119.8(2) . . ?
C6 N2 N3 118.5(3) . . ?
C6 N2 Ce1 123.4(2) . . ?
N3 N2 Ce1 118.1(2) . . ?
C7 N3 N2 116.1(3) . . ?
C7 N3 H3 122(2) . . ?
N2 N3 H3 119(2) . . ?
C8 N4 C11 114.8(3) . . ?
C10 N5 C9 114.8(4) . . ?
O4 N6 O2 121.2(3) . . ?
O4 N6 O3 121.6(3) . . ?
O2 N6 O3 117.2(3) . . ?
O6 N7 O5 121.5(2) . 2 ?
O6 N7 O5 121.5(2) . . ?
O5 N7 O5 116.9(4) 2 . ?
C7 O1 Ce1 124.6(2) . . ?
N6 O2 Ce1 100.1(2) . . ?
N6 O3 Ce1 94.8(2) . . ?
N7 O5 Ce1 97.5(2) . . ?
N1 C1 C2 122.2(3) . . ?
N1 C1 C6 117.6(3) . . ?
C2 C1 C6 120.2(3) . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
N1 C5 C4 123.6(4) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N2 C6 C1 119.5(3) . . ?
N2 C6 H6A 120.3 . . ?
C1 C6 H6A 120.3 . . ?
O1 C7 N3 122.3(3) . . ?
O1 C7 C8 121.2(3) . . ?
N3 C7 C8 116.5(3) . . ?
N4 C8 C9 122.2(3) . . ?
N4 C8 C7 118.0(3) . . ?
C9 C8 C7 119.8(3) . . ?
N5 C9 C8 122.9(4) . . ?
N5 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
N5 C10 C11 122.8(4) . . ?
N5 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
N4 C11 C10 122.4(4) . . ?
N4 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C12 O7 H7 112(7) . . ?
O7 C12 H12A 109.5 . . ?
O7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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 N2 N3 C7 170.5(3) . . . . ?
Ce1 N2 N3 C7 -7.1(4) . . . . ?
O4 N6 O2 Ce1 171.7(3) . . . . ?
O3 N6 O2 Ce1 -7.9(3) . . . . ?
O4 N6 O3 Ce1 -172.1(3) . . . . ?
O2 N6 O3 Ce1 7.5(3) . . . . ?
O6 N7 O5 Ce1 180.000(0) . . . . ?
O5 N7 O5 Ce1 0.000(1) 2 . . . ?
C5 N1 C1 C2 -1.1(5) . . . . ?
Ce1 N1 C1 C2 172.3(3) . . . . ?
C5 N1 C1 C6 176.4(3) . . . . ?
Ce1 N1 C1 C6 -10.2(4) . . . . ?
N1 C1 C2 C3 0.6(6) . . . . ?
C6 C1 C2 C3 -176.8(4) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C1 N1 C5 C4 0.4(5) . . . . ?
Ce1 N1 C5 C4 -172.9(3) . . . . ?
C3 C4 C5 N1 0.9(6) . . . . ?
N3 N2 C6 C1 -176.0(3) . . . . ?
Ce1 N2 C6 C1 1.5(4) . . . . ?
N1 C1 C6 N2 6.0(5) . . . . ?
C2 C1 C6 N2 -176.5(3) . . . . ?
Ce1 O1 C7 N3 3.2(5) . . . . ?
Ce1 O1 C7 C8 -176.0(2) . . . . ?
N2 N3 C7 O1 3.0(5) . . . . ?
N2 N3 C7 C8 -177.7(3) . . . . ?
C11 N4 C8 C9 -0.8(5) . . . . ?
C11 N4 C8 C7 -179.5(3) . . . . ?
O1 C7 C8 N4 170.7(3) . . . . ?
N3 C7 C8 N4 -8.6(5) . . . . ?
O1 C7 C8 C9 -8.1(5) . . . . ?
N3 C7 C8 C9 172.6(3) . . . . ?
C10 N5 C9 C8 -0.5(6) . . . . ?
N4 C8 C9 N5 0.7(6) . . . . ?
C7 C8 C9 N5 179.4(3) . . . . ?
C9 N5 C10 C11 0.6(6) . . . . ?
C8 N4 C11 C10 0.8(6) . . . . ?
N5 C10 C11 N4 -0.8(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
C12 H12C O5 0.96 2.58 3.504(6) 162.6 1_545 yes
O7 H7 O3 0.89(10) 2.23(10) 3.038(5) 150(10) 6_565 yes
C11 H11 O4 0.93 2.64 3.198(5) 119.4 2_545 yes
C10 H10 O2 0.93 2.49 3.330(5) 150.4 8_455 yes
C6 H6A O7 0.93 2.49 3.178(5) 130.7 . yes
C5 H5 O5 0.93 2.41 2.924(4) 115.0 . yes
C2 H2 O4 0.93 2.66 3.476(5) 147.0 6_565 yes
N3 H3 O7 0.84(4) 2.06(4) 2.843(5) 154(3) . yes
O7 H7 O3 0.89(10) 2.23(10) 3.038(5) 150(10) 6_565 yes
N3 H3 O7 0.84(4) 2.06(4) 2.843(5) 154(3) . yes

_refine_diff_density_max         0.654
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.104

