# 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 2023

####################################################################### 
# 
# 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. 
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data_meb1505a
_database_code_depnum_ccdc_archive 'CCDC 2252469'
loop_
_audit_author_name
_audit_author_address
'Frank W. Heinemann'
;Friedrich Alexander Universitaet Erlangen Nuernberg
Germany
;
_audit_update_record             
;
2023-03-30 deposited with the CCDC.	2023-09-29 downloaded from the CCDC.
;
_audit_creation_date             2023-03-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '6(C2 H6 O S), C30 H22 N2 O16'
_chemical_formula_sum            'C42 H58 N2 O22 S6'
_chemical_formula_weight         1135.26
_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'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0803(11)
_cell_length_b                   19.8625(19)
_cell_length_c                   14.0812(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.710(3)
_cell_angle_gamma                90
_cell_volume                     2637.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0974 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.9575.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            72015
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.155
_diffrn_reflns_theta_min         1.855
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_source         'ImuS micro-focus tube'
_diffrn_radiation_monochromator  'Quazar focussing montel optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 83.33
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4586
_reflns_number_total             5843
_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_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5843
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²+3.2483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0981
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C13(H13)
2.b Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4A), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
S1 S 0.90431(6) 0.21343(3) 0.37942(4) 0.02130(13) Uani 1 1 d . . . . .
S2 S 0.64898(6) 0.09535(3) -0.00378(4) 0.02245(13) Uani 1 1 d . . . . .
S3 S 0.31903(7) 0.22409(3) 0.61474(5) 0.02554(14) Uani 1 1 d . . . . .
O1 O 0.76157(19) 0.14643(8) 0.81889(12) 0.0267(4) Uani 1 1 d . . . . .
O2 O 0.77596(17) 0.18540(8) 0.67456(11) 0.0202(3) Uani 1 1 d . . . . .
H2 H 0.794(3) 0.2276(14) 0.714(2) 0.030 Uiso 1 1 d . U . . .
O3 O 0.80054(17) -0.11983(7) 0.74410(11) 0.0203(3) Uani 1 1 d . . . . .
O4 O 0.81625(17) -0.10203(9) 0.90524(11) 0.0239(4) Uani 1 1 d . . . . .
H4 H 0.812(3) -0.1474(15) 0.907(2) 0.036 Uiso 1 1 d . U . . .
O5 O 0.65903(14) 0.07860(7) 0.57757(10) 0.0110(3) Uani 1 1 d . . . . .
O6 O 0.48614(15) -0.06649(7) 0.70774(10) 0.0165(3) Uani 1 1 d . . . . .
O7 O 0.82827(15) 0.01935(7) 0.48513(10) 0.0164(3) Uani 1 1 d . . . . .
O8 O 0.66145(15) -0.05836(7) 0.41213(10) 0.0139(3) Uani 1 1 d . . . . .
O9 O 0.81595(17) 0.20444(7) 0.26697(11) 0.0212(3) Uani 1 1 d . . . . .
O10 O 0.56400(17) 0.15817(9) -0.03688(13) 0.0296(4) Uani 1 1 d . . . . .
O11 O 0.19789(18) 0.27186(9) 0.56535(14) 0.0341(4) Uani 1 1 d . . . . .
N1 N 1.20752(17) 0.07759(8) 0.70929(12) 0.0120(3) Uani 1 1 d . . . . .
H1 H 1.260(2) 0.0695(11) 0.6544(17) 0.018 Uiso 1 1 d . U . . .
C1 C 1.0791(2) 0.05021(9) 0.68706(14) 0.0112(4) Uani 1 1 d . . . . .
H1A H 1.036689 0.027966 0.623788 0.013 Uiso 1 1 calc R U . . .
C2 C 1.0056(2) 0.05341(10) 0.75417(15) 0.0129(4) Uani 1 1 d . . . . .
C3 C 1.0716(2) 0.08633(11) 0.84608(16) 0.0198(5) Uani 1 1 d . . . . .
H3 H 1.025149 0.089352 0.894042 0.024 Uiso 1 1 calc R U . . .
C4 C 1.2047(2) 0.11475(12) 0.86800(16) 0.0219(5) Uani 1 1 d . . . . .
H4A H 1.249724 0.137439 0.930574 0.026 Uiso 1 1 calc R U . . .
C5 C 1.2710(2) 0.10962(11) 0.79772(15) 0.0170(4) Uani 1 1 d . . . . .
H5 H 1.362221 0.128919 0.812028 0.020 Uiso 1 1 calc R U . . .
C6 C 0.8605(2) 0.02266(10) 0.72312(14) 0.0120(4) Uani 1 1 d . . . . .
H6 H 0.852915 -0.012838 0.671096 0.014 Uiso 1 1 calc R U . . .
C7 C 0.7256(2) 0.06888(10) 0.68276(14) 0.0111(4) Uani 1 1 d . . . . .
C8 C 0.6521(2) 0.02277(10) 0.73876(14) 0.0121(4) Uani 1 1 d . . . . .
H8 H 0.608856 0.048839 0.781232 0.014 Uiso 1 1 calc R U . . .
C9 C 0.8021(2) -0.00655(10) 0.80257(15) 0.0131(4) Uani 1 1 d . . . . .
H9 H 0.844047 0.016512 0.869728 0.016 Uiso 1 1 calc R U . . .
C10 C 0.7552(2) 0.13847(10) 0.73219(15) 0.0146(4) Uani 1 1 d . . . . .
C11 C 0.8078(2) -0.08234(11) 0.81372(15) 0.0151(4) Uani 1 1 d . . . . .
C12 C 0.6082(2) 0.02041(9) 0.51742(14) 0.0101(4) Uani 1 1 d . . . . .
C13 C 0.5405(2) -0.03503(9) 0.56375(14) 0.0100(4) Uani 1 1 d . . . . .
H13 H 0.574275 -0.080406 0.551400 0.012 Uiso 1 1 calc R U . . .
C14 C 0.5526(2) -0.02913(10) 0.67321(15) 0.0119(4) Uani 1 1 d . . . . .
C15 C 0.7131(2) -0.00673(10) 0.46987(14) 0.0114(4) Uani 1 1 d . . . . .
C16 C 1.0038(3) 0.13746(11) 0.41227(19) 0.0263(5) Uani 1 1 d . . . . .
H16A H 1.064412 0.138805 0.484121 0.039 Uiso 1 1 calc R U . . .
H16B H 0.938809 0.099098 0.400308 0.039 Uiso 1 1 calc R U . . .
H16C H 1.063022 0.132657 0.370454 0.039 Uiso 1 1 calc R U . . .
C17 C 0.7829(4) 0.19832(15) 0.4433(2) 0.0435(8) Uani 1 1 d . . . . .
H17A H 0.832134 0.203200 0.516653 0.065 Uiso 1 1 calc R U . . .
H17B H 0.704989 0.230882 0.420097 0.065 Uiso 1 1 calc R U . . .
H17C H 0.744830 0.152575 0.428222 0.065 Uiso 1 1 calc R U . . .
C18 C 0.6208(4) 0.06775(15) 0.1084(2) 0.0428(7) Uani 1 1 d . . . . .
H18A H 0.674695 0.026332 0.133358 0.064 Uiso 1 1 calc R U . . .
H18B H 0.652640 0.102752 0.160615 0.064 Uiso 1 1 calc R U . . .
H18C H 0.519576 0.059017 0.092698 0.064 Uiso 1 1 calc R U . . .
C19 C 0.8293(3) 0.11958(15) 0.05661(18) 0.0334(6) Uani 1 1 d . . . . .
H19A H 0.888163 0.079297 0.079331 0.050 Uiso 1 1 calc R U . . .
H19B H 0.860846 0.144634 0.008478 0.050 Uiso 1 1 calc R U . . .
H19C H 0.838228 0.148168 0.115279 0.050 Uiso 1 1 calc R U . . .
C20 C 0.4479(3) 0.27000(15) 0.7127(2) 0.0427(7) Uani 1 1 d . . . . .
H20A H 0.529098 0.240778 0.747076 0.064 Uiso 1 1 calc R U . . .
H20B H 0.479728 0.308732 0.683241 0.064 Uiso 1 1 calc R U . . .
H20C H 0.406135 0.285815 0.761785 0.064 Uiso 1 1 calc R U . . .
C21 C 0.4104(3) 0.21596(12) 0.52772(19) 0.0288(5) Uani 1 1 d . . . . .
H21A H 0.490960 0.185256 0.555922 0.043 Uiso 1 1 calc R U . . .
H21B H 0.345648 0.197943 0.463203 0.043 Uiso 1 1 calc R U . . .
H21C H 0.445009 0.260214 0.516181 0.043 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
S1 O9 1.5282(16) . ?
S1 C16 1.780(2) . ?
S1 C17 1.782(3) . ?
S2 O10 1.4920(17) . ?
S2 C18 1.787(3) . ?
S2 C19 1.779(3) . ?
S3 O11 1.5081(18) . ?
S3 C20 1.776(3) . ?
S3 C21 1.782(2) . ?
O1 C10 1.210(2) . ?
O2 H2 0.98(3) . ?
O2 C10 1.300(2) . ?
O3 C11 1.212(3) . ?
O4 H4 0.90(3) . ?
O4 C11 1.320(2) . ?
O5 C7 1.407(2) . ?
O5 C12 1.417(2) . ?
O6 C14 1.211(2) . ?
O7 C15 1.219(2) . ?
O8 C15 1.298(2) . ?
N1 H1 1.09(2) . ?
N1 C1 1.335(3) . ?
N1 C5 1.342(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.393(3) . ?
C2 C3 1.391(3) . ?
C2 C6 1.501(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4A 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C6 H6 1.0000 . ?
C6 C7 1.571(3) . ?
C6 C9 1.549(3) . ?
C7 C8 1.557(3) . ?
C7 C10 1.529(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.573(3) . ?
C8 C14 1.505(3) . ?
C9 H9 1.0000 . ?
C9 C11 1.513(3) . ?
C12 C13 1.555(3) . ?
C12 C13 1.558(3) 3_656 ?
C12 C15 1.536(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.507(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
O9 S1 C16 103.80(10) . . ?
O9 S1 C17 104.51(13) . . ?
C16 S1 C17 98.66(12) . . ?
O10 S2 C18 106.23(13) . . ?
O10 S2 C19 107.44(12) . . ?
C19 S2 C18 96.63(14) . . ?
O11 S3 C20 106.61(11) . . ?
O11 S3 C21 105.74(11) . . ?
C20 S3 C21 99.57(14) . . ?
C10 O2 H2 107.5(15) . . ?
C11 O4 H4 109.6(18) . . ?
C7 O5 C12 117.02(14) . . ?
C1 N1 H1 116.5(12) . . ?
C1 N1 C5 120.99(17) . . ?
C5 N1 H1 122.3(12) . . ?
N1 C1 H1A 119.1 . . ?
N1 C1 C2 121.76(18) . . ?
C2 C1 H1A 119.1 . . ?
C1 C2 C6 118.76(17) . . ?
C3 C2 C1 117.31(18) . . ?
C3 C2 C6 123.92(18) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.33(19) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 C3 119.09(19) . . ?
C5 C4 H4A 120.5 . . ?
N1 C5 C4 120.52(19) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C2 C6 H6 108.3 . . ?
C2 C6 C7 119.84(16) . . ?
C2 C6 C9 121.48(16) . . ?
C7 C6 H6 108.3 . . ?
C9 C6 H6 108.3 . . ?
C9 C6 C7 88.78(14) . . ?
O5 C7 C6 119.38(15) . . ?
O5 C7 C8 118.62(16) . . ?
O5 C7 C10 107.39(15) . . ?
C8 C7 C6 88.81(14) . . ?
C10 C7 C6 111.03(16) . . ?
C10 C7 C8 110.66(15) . . ?
C7 C8 H8 112.6 . . ?
C7 C8 C9 88.47(14) . . ?
C9 C8 H8 112.6 . . ?
C14 C8 C7 115.20(16) . . ?
C14 C8 H8 112.6 . . ?
C14 C8 C9 113.23(16) . . ?
C6 C9 C8 89.02(14) . . ?
C6 C9 H9 111.7 . . ?
C8 C9 H9 111.7 . . ?
C11 C9 C6 115.95(16) . . ?
C11 C9 C8 114.92(16) . . ?
C11 C9 H9 111.7 . . ?
O1 C10 O2 124.96(19) . . ?
O1 C10 C7 120.63(18) . . ?
O2 C10 C7 114.37(16) . . ?
O3 C11 O4 124.9(2) . . ?
O3 C11 C9 122.56(18) . . ?
O4 C11 C9 112.52(18) . . ?
O5 C12 C13 116.51(15) . . ?
O5 C12 C13 109.71(15) . 3_656 ?
O5 C12 C15 112.80(15) . . ?
C13 C12 C13 89.36(14) . 3_656 ?
C15 C12 C13 112.21(15) . 3_656 ?
C15 C12 C13 113.97(15) . . ?
C12 C13 C12 90.64(14) . 3_656 ?
C12 C13 H13 109.8 3_656 . ?
C12 C13 H13 109.8 . . ?
C14 C13 C12 119.03(16) . . ?
C14 C13 C12 116.38(15) . 3_656 ?
C14 C13 H13 109.8 . . ?
O6 C14 C8 121.11(18) . . ?
O6 C14 C13 120.47(17) . . ?
C8 C14 C13 118.39(16) . . ?
O7 C15 O8 126.33(18) . . ?
O7 C15 C12 122.27(17) . . ?
O8 C15 C12 111.39(16) . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S2 C18 H18A 109.5 . . ?
S2 C18 H18B 109.5 . . ?
S2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S2 C19 H19A 109.5 . . ?
S2 C19 H19B 109.5 . . ?
S2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S3 C20 H20A 109.5 . . ?
S3 C20 H20B 109.5 . . ?
S3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S3 C21 H21A 109.5 . . ?
S3 C21 H21B 109.5 . . ?
S3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 S1 0.98(3) 2.50(3) 3.3754(16) 149(2) 4_566 yes
O2 H2 O9 0.98(3) 1.52(3) 2.504(2) 176(3) 4_566 yes
O4 H4 S3 0.90(3) 2.84(3) 3.6871(18) 157(2) 2_646 yes
O4 H4 O11 0.90(3) 1.66(3) 2.551(2) 168(3) 2_646 yes
N1 H1 O7 1.09(2) 2.56(2) 3.261(2) 121.4(15) 3_756 yes
N1 H1 O8 1.09(2) 1.44(2) 2.532(2) 176(2) 3_756 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
O5 C7 C8 C9 139.72(17) . . . . ?
O5 C7 C8 C14 24.7(2) . . . . ?
O5 C7 C10 O1 152.37(19) . . . . ?
O5 C7 C10 O2 -29.5(2) . . . . ?
O5 C12 C13 C12 111.79(18) . . . 3_656 ?
O5 C12 C13 C14 -9.2(2) . . . . ?
O5 C12 C15 O7 1.3(3) . . . . ?
O5 C12 C15 O8 -177.50(15) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
N1 C1 C2 C6 178.82(17) . . . . ?
C1 N1 C5 C4 0.2(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C6 C7 -100.7(2) . . . . ?
C1 C2 C6 C9 150.45(18) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C6 C7 O5 94.5(2) . . . . ?
C2 C6 C7 C8 -142.92(17) . . . . ?
C2 C6 C7 C10 -31.2(2) . . . . ?
C2 C6 C9 C8 141.38(18) . . . . ?
C2 C6 C9 C11 -101.2(2) . . . . ?
C3 C2 C6 C7 78.1(3) . . . . ?
C3 C2 C6 C9 -30.7(3) . . . . ?
C3 C4 C5 N1 0.0(3) . . . . ?
C5 N1 C1 C2 -0.2(3) . . . . ?
C6 C2 C3 C4 -178.5(2) . . . . ?
C6 C7 C8 C9 16.52(14) . . . . ?
C6 C7 C8 C14 -98.55(17) . . . . ?
C6 C7 C10 O1 -75.5(2) . . . . ?
C6 C7 C10 O2 102.7(2) . . . . ?
C6 C9 C11 O3 -29.5(3) . . . . ?
C6 C9 C11 O4 152.74(17) . . . . ?
C7 O5 C12 C13 137.87(16) . . . 3_656 ?
C7 O5 C12 C13 38.4(2) . . . . ?
C7 O5 C12 C15 -96.24(18) . . . . ?
C7 C6 C9 C8 16.59(14) . . . . ?
C7 C6 C9 C11 134.01(17) . . . . ?
C7 C8 C9 C6 -16.76(14) . . . . ?
C7 C8 C9 C11 -135.09(17) . . . . ?
C7 C8 C14 O6 -177.78(18) . . . . ?
C7 C8 C14 C13 4.0(2) . . . . ?
C8 C7 C10 O1 21.5(3) . . . . ?
C8 C7 C10 O2 -160.35(17) . . . . ?
C8 C9 C11 O3 72.3(2) . . . . ?
C8 C9 C11 O4 -105.42(19) . . . . ?
C9 C6 C7 O5 -139.32(17) . . . . ?
C9 C6 C7 C8 -16.77(14) . . . . ?
C9 C6 C7 C10 94.95(16) . . . . ?
C9 C8 C14 O6 82.4(2) . . . . ?
C9 C8 C14 C13 -95.8(2) . . . . ?
C10 C7 C8 C9 -95.55(17) . . . . ?
C10 C7 C8 C14 149.39(17) . . . . ?
C12 O5 C7 C6 59.0(2) . . . . ?
C12 O5 C7 C8 -47.2(2) . . . . ?
C12 O5 C7 C10 -173.53(15) . . . . ?
C12 C13 C14 O6 63.7(2) 3_656 . . . ?
C12 C13 C14 O6 170.56(18) . . . . ?
C12 C13 C14 C8 -11.2(3) . . . . ?
C12 C13 C14 C8 -118.06(19) 3_656 . . . ?
C13 C12 C13 C12 -0.003(0) 3_656 . . 3_656 ?
C13 C12 C13 C14 -121.0(2) 3_656 . . . ?
C13 C12 C15 O7 -134.52(19) . . . . ?
C13 C12 C15 O7 125.79(19) 3_656 . . . ?
C13 C12 C15 O8 46.7(2) . . . . ?
C13 C12 C15 O8 -53.0(2) 3_656 . . . ?
C14 C8 C9 C6 100.12(17) . . . . ?
C14 C8 C9 C11 -18.2(2) . . . . ?
C15 C12 C13 C12 -114.13(18) . . . 3_656 ?
C15 C12 C13 C14 124.91(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


# start Validation Reply Form
_vrf_PLAT353_meb1505a            
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H1       .       1.09 Ang.  
RESPONSE: H1 is involved in hydrogen bonding with symmetry equivalent atoms 
of O7 and O8 accounting for an elongation of this N-H bond.
;
# end Validation Reply Form

#===END OF ALL DATA

####################################################################### 
# 
# 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_20229003
_database_code_depnum_ccdc_archive 'CCDC 2257007'
loop_
_audit_author_name
_audit_author_address
'Teresa Gonzalez'
;IVIC
Venezuela
;
_audit_update_record             
;
2023-04-17 deposited with the CCDC.	2023-09-29 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 O6, C8 H8 N O2, 2(H2 O)'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H15 N O10'
_chemical_formula_iupac          ?
_chemical_formula_weight         369.28
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' 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 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   7.4691(2)
_cell_length_b                   10.2107(2)
_cell_length_c                   11.3913(2)
_cell_angle_alpha                71.336(2)
_cell_angle_beta                 78.812(2)
_cell_angle_gamma                77.041(2)
_cell_volume                     795.04(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_reflns_used    5266
_cell_measurement_theta_min      4.63
_cell_measurement_theta_max      74.32
_cell_special_details            
;
;

_exptl_crystal_description       Plate
_exptl_crystal_colour            beige

_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    1.150
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_T_max  1.000

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  
;
XtaLAB AFC11 (RCD3): quarter-chi single
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 5.8140

# number of measured reflections (redundant set)
_diffrn_reflns_number            7565
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         74.49
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3118
# number of observed reflections (> n sig(I))
_reflns_number_gt                2891
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)
;
_computing_structure_solution    
;
SHELXT 2014/5 (Sheldrick, 2015)
;
_computing_structure_refinement  
;
SHELXL 2014/7 (Sheldrick, 2015)
;
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2009)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0584P)²+0.1325P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed


# Permitted for _refine_ls_hydrogen_treatment :
# refall            - refined all H-atom parameters
# refxyz            - refined H-atom coordinates only
# refU              - refined H-atom U only
# noref             - no refinement of H-atom parameters
# constr            - H-atom parameters constrained
# hetero            - H-atom parameters constrained for H on C,
#                     all H-atom parameters refined for H on
#                     heteroatoms
# heteroxyz         - H-atom parameters constrained for H on C,
#                     refined H-atom coordinates only for H
#                     on heteroatoms
# heteroU           - H-atom parameters constrained for H on C,
#                     refined H-atom U's only for H on
#                     heteroatoms
# heteronoref       - H-atom parameters constrained for H on C,
#                     no refinement of H-atom parameters for
#                     H on heteroatoms
# hetero-mixed      - H-atom parameters constrained for H on C
#                     and some heteroatoms, all H-atom
#                     parameters refined for H on remaining
#                     heteroatoms.
# heteroxyz-mixed   - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     coordinates only for H on remaining
#                     heteroatoms.
# heteroU-mixed     - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     U's only for H on remaining heteroatoms
# heteronoref-mixed - H-atom parameters constrained for H on C
#                     and some heteroatoms, no refinement of
#                     H-atom parameters for H on remaining
#                     heteroatoms
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         3118
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.77382(17) 0.56167(10) 0.19709(8) 1.000 0.0585(4) d . . .
O2 O Uani 0.70567(18) 0.39762(11) 0.37207(9) 1.000 0.0654(4) d . . .
O3 O Uani 0.85855(12) 0.71493(8) 0.31535(7) 1.000 0.0382(3) d . . .
O4 O Uani 0.98182(14) 0.94498(9) 0.16665(8) 1.000 0.0473(3) d . . .
O5 O Uani 0.97779(16) 1.02001(10) 0.33170(8) 1.000 0.0524(3) d . . .
O6 O Uani 0.77556(16) 0.62730(11) 0.69339(8) 1.000 0.0570(3) d . . .
C1 C Uani 0.75359(19) 0.51118(13) 0.31336(11) 1.000 0.0430(4) d . . .
C2 C Uani 0.79172(16) 0.59749(12) 0.38865(10) 1.000 0.0363(3) d . . .
C3 C Uani 0.89431(16) 0.80257(12) 0.37173(11) 1.000 0.0353(3) d . . .
C4 C Uani 0.95797(17) 0.93035(12) 0.27757(11) 1.000 0.0375(3) d . . .
C5 C Uani 0.87042(18) 0.77841(13) 0.49608(11) 1.000 0.0402(4) d . . .
C6 C Uani 0.80069(18) 0.65409(13) 0.57789(11) 1.000 0.0405(4) d . . .
C7 C Uani 0.76221(17) 0.56462(12) 0.51347(11) 1.000 0.0397(4) d . . .
O7 O Uani 0.61576(16) 1.15752(10) 0.51145(8) 1.000 0.0550(3) d . . .
O8 O Uani 0.62151(16) 1.20149(11) 0.68968(9) 1.000 0.0588(4) d . . .
N1 N Uani 0.29940(15) 0.61436(11) 0.90600(10) 1.000 0.0420(3) d . . .
O1W O Uani 0.21231(16) 0.17643(11) 0.97079(9) 1.000 0.0565(3) d G . .
C8 C Uani 0.59173(17) 1.12723(12) 0.63487(11) 1.000 0.0396(3) d . . .
C9 C Uani 0.52101(18) 0.99335(12) 0.69478(11) 1.000 0.0409(4) d . . .
C10 C Uani 0.48083(18) 0.94776(13) 0.81705(12) 1.000 0.0423(4) d . . .
C11 C Uani 0.40598(17) 0.82059(12) 0.89018(11) 1.000 0.0371(3) d . . .
C12 C Uani 0.37132(18) 0.72708(13) 0.83615(11) 1.000 0.0394(4) d . . .
C13 C Uani 0.2567(2) 0.58598(14) 1.02994(12) 1.000 0.0476(4) d . . .
C14 C Uani 0.2893(2) 0.67332(15) 1.08946(12) 1.000 0.0537(5) d . . .
C15 C Uani 0.3633(2) 0.79094(14) 1.01957(12) 1.000 0.0489(4) d . . .
O2W O Uani 0.06913(14) 0.24216(10) 0.18335(9) 1.000 0.0496(3) d G . .
H5 H Uiso 1.01080 1.08910 0.27850 1.000 0.0790 c RU . .
H5A H Uiso 0.89870 0.84170 0.53000 1.000 0.0480 c RU . .
H7A H Uiso 0.71630 0.48300 0.55940 1.000 0.0480 c RU . .
H1 H Uiso 0.275(3) 0.552(2) 0.8650(18) 1.000 0.078(6) d . . .
H7 H Uiso 0.65130 1.23320 0.48070 1.000 0.0820 c RU . .
H9 H Uiso 0.50490 0.94100 0.64540 1.000 0.0490 c RU . .
H10 H Uiso 0.50250 1.00270 0.86230 1.000 0.0510 c RU . .
H12 H Uiso 0.39850 0.74300 0.75010 1.000 0.0470 c RU . .
H13 H Uiso 0.20480 0.50690 1.07550 1.000 0.0570 c RU . .
H14 H Uiso 0.26200 0.65370 1.17590 1.000 0.0640 c RU . .
H15 H Uiso 0.38510 0.85140 1.05930 1.000 0.0590 c RU . .
H1WA H Uiso 0.21540 0.25280 0.91220 1.000 0.0850 d GU . .
H1WB H Uiso 0.14000 0.13080 0.95750 1.000 0.0850 d GU . .
H2WA H Uiso 0.14030 0.27700 0.21030 1.000 0.0740 d GU . .
H2WB H Uiso 0.13120 0.22560 0.11720 1.000 0.0740 d GU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2502(15) . . yes
O2 C1 1.2316(17) . . yes
O3 C2 1.3602(14) . . yes
O3 C3 1.3514(15) . . yes
O4 C4 1.2060(15) . . yes
O5 C4 1.3030(16) . . yes
O6 C6 1.2401(15) . . yes
O5 H5 0.8200 . . no
C1 C2 1.5114(18) . . no
C2 C7 1.3376(16) . . no
C3 C4 1.5045(17) . . no
C3 C5 1.3406(17) . . no
C5 C6 1.4499(18) . . no
C6 C7 1.4437(18) . . no
O7 C8 1.3241(15) . . yes
O8 C8 1.2028(17) . . yes
N1 C12 1.3310(17) . . yes
N1 C13 1.3356(17) . . yes
C5 H5A 0.9300 . . no
C7 H7A 0.9300 . . no
O7 H7 0.8200 . . no
N1 H1 0.97(2) . . no
C8 C9 1.4834(18) . . no
C9 C10 1.3161(17) . . no
C10 C11 1.4646(18) . . no
C11 C12 1.3807(18) . . no
C11 C15 1.3932(17) . . no
C13 C14 1.365(2) . . no
C14 C15 1.377(2) . . no
O1W H1WB 0.8500 . . no
O1W H1WA 0.8500 . . no
C9 H9 0.9300 . . no
C10 H10 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15 0.9300 . . no
O2W H2WA 0.8500 . . no
O2W H2WB 0.8500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O3 C3 118.19(9) . . . yes
C4 O5 H5 109.00 . . . no
O1 C1 O2 125.99(13) . . . yes
O1 C1 C2 116.93(12) . . . yes
O2 C1 C2 117.08(11) . . . yes
O3 C2 C7 122.89(11) . . . yes
C1 C2 C7 124.56(11) . . . no
O3 C2 C1 112.56(9) . . . yes
O3 C3 C4 111.46(10) . . . yes
C4 C3 C5 125.13(12) . . . no
O3 C3 C5 123.38(11) . . . yes
O4 C4 O5 126.29(12) . . . yes
O5 C4 C3 111.35(10) . . . yes
O4 C4 C3 122.34(11) . . . yes
C3 C5 C6 120.32(12) . . . no
O6 C6 C5 122.78(12) . . . yes
C5 C6 C7 114.31(10) . . . no
O6 C6 C7 122.90(12) . . . yes
C2 C7 C6 120.89(11) . . . no
C12 N1 C13 122.50(12) . . . yes
C3 C5 H5A 120.00 . . . no
C6 C5 H5A 120.00 . . . no
C2 C7 H7A 120.00 . . . no
C6 C7 H7A 120.00 . . . no
C8 O7 H7 109.00 . . . no
C13 N1 H1 119.0(12) . . . no
C12 N1 H1 118.5(12) . . . no
O7 C8 C9 111.45(11) . . . yes
O7 C8 O8 123.36(12) . . . yes
O8 C8 C9 125.18(11) . . . yes
C8 C9 C10 120.78(12) . . . no
C9 C10 C11 127.59(12) . . . no
C12 C11 C15 117.11(12) . . . no
C10 C11 C12 122.72(11) . . . no
C10 C11 C15 120.17(12) . . . no
N1 C12 C11 120.69(11) . . . yes
N1 C13 C14 119.82(13) . . . yes
C13 C14 C15 118.97(12) . . . no
C11 C15 C14 120.91(13) . . . no
H1WA O1W H1WB 109.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C11 C10 H10 116.00 . . . no
C9 C10 H10 116.00 . . . no
N1 C12 H12 120.00 . . . no
C11 C12 H12 120.00 . . . no
C14 C13 H13 120.00 . . . no
N1 C13 H13 120.00 . . . no
C13 C14 H14 121.00 . . . no
C15 C14 H14 121.00 . . . no
C11 C15 H15 120.00 . . . no
C14 C15 H15 120.00 . . . no
H2WA O2W H2WB 104.00 . . . no

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
C3 O3 C2 C1 178.58(11) . . . . no
C3 O3 C2 C7 -0.80(18) . . . . no
C2 O3 C3 C4 -177.15(10) . . . . no
C2 O3 C3 C5 1.23(18) . . . . no
O1 C1 C2 O3 -5.14(18) . . . . no
O1 C1 C2 C7 174.23(13) . . . . no
O2 C1 C2 O3 174.79(13) . . . . no
O2 C1 C2 C7 -5.9(2) . . . . no
O3 C2 C7 C6 0.0(2) . . . . no
C1 C2 C7 C6 -179.31(12) . . . . no
O3 C3 C4 O4 -3.66(18) . . . . no
O3 C3 C4 O5 174.78(11) . . . . no
C5 C3 C4 O4 178.00(14) . . . . no
C5 C3 C4 O5 -3.56(19) . . . . no
O3 C3 C5 C6 -0.8(2) . . . . no
C4 C3 C5 C6 177.33(12) . . . . no
C3 C5 C6 O6 -179.73(14) . . . . no
C3 C5 C6 C7 0.0(2) . . . . no
O6 C6 C7 C2 -179.88(14) . . . . no
C5 C6 C7 C2 0.41(19) . . . . no
C13 N1 C12 C11 0.3(2) . . . . no
C12 N1 C13 C14 -1.0(2) . . . . no
O7 C8 C9 C10 -177.19(13) . . . . no
O8 C8 C9 C10 1.7(2) . . . . no
C8 C9 C10 C11 178.37(13) . . . . no
C9 C10 C11 C12 1.7(2) . . . . no
C9 C10 C11 C15 -177.09(14) . . . . no
C10 C11 C12 N1 -178.52(13) . . . . no
C15 C11 C12 N1 0.3(2) . . . . no
C10 C11 C15 C14 178.67(14) . . . . no
C12 C11 C15 C14 -0.2(2) . . . . no
N1 C13 C14 C15 1.1(2) . . . . no
C13 C14 C15 C11 -0.5(2) . . . . no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1 O1 0.97(2) 1.67(2) 2.6362(16) 176(2) 2_666 yes
N1 H1 O2 0.97(2) 2.563(19) 3.2166(15) 125.1(15) 2_666 yes
O1W H1WA O1 0.8500 1.9100 2.7556(14) 170.00 2_666 yes
O1W H1WB O4 0.8500 2.2200 3.0033(15) 153.00 2_666 yes
O2W H2WA O6 0.8500 1.9400 2.7599(15) 160.00 2_666 yes
O2W H2WB O1W 0.8500 1.8500 2.6777(14) 166.00 1_554 yes
O5 H5 O2W 0.8200 1.6900 2.5019(14) 173.00 1_665 yes
O7 H7 O2 0.8200 1.8200 2.6106(15) 163.00 1_565 yes
C10 H10 O8 0.9300 2.5200 2.8539(18) 101.00 . yes
C13 H13 O6 0.9300 2.5700 3.2064(16) 126.00 2_667 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;

