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

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

data_20180615a
_database_code_depnum_ccdc_archive 'CCDC 1875915'
loop_
_audit_author_name
_audit_author_address
'Bo Zhou'
;Beijing normal university
China
;
_audit_update_record             
;
2018-12-18 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;
_audit_creation_date             2018-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H5 O6, C3 H7 N6, 2(H2 O)'
_chemical_formula_sum            'C12 H16 N6 O8'
_chemical_formula_weight         372.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1
_chemical_oxdiff_usercomment     ZB-5201
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                   9.3092(13)
_cell_length_b                   9.8441(14)
_cell_length_c                   10.1956(14)
_cell_angle_alpha                63.563(14)
_cell_angle_beta                 71.551(13)
_cell_angle_gamma                73.220(12)
_cell_volume                     781.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1244
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0950
_cell_measurement_theta_min      4.0400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5343
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.593
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  20.00   1.00    8.00    --  -11.20 -77.00   0.00  101
  2  ω    -61.00  37.00   1.00    8.00    --   12.45 -57.00 120.00   98
  3  ω    -14.00  79.00   1.00    8.00    --   12.45  57.00 -90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0478403000
_diffrn_orient_matrix_UB_12      -0.0521335000
_diffrn_orient_matrix_UB_13      0.0572426000
_diffrn_orient_matrix_UB_21      0.0449820000
_diffrn_orient_matrix_UB_22      -0.0596344000
_diffrn_orient_matrix_UB_23      -0.0242800000
_diffrn_orient_matrix_UB_31      0.0483824000
_diffrn_orient_matrix_UB_32      -0.0200779000
_diffrn_orient_matrix_UB_33      0.0497476000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1942
_reflns_number_total             3115
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    ?
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3115
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.057
_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)+(0.0572P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O3-H3
 0.85 with sigma of 0.02
 O8-H8B
 0.9 with sigma of 0.02
3.a Free rotating group:
 O7(H7A,H7B), O8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3B), C3(H3A), C6(H6), C5(H5A)
3.c X=CH2 refined with riding coordinates:
 N6(H6A,H6B), N5(H5B,H5C), N4(H4A,H4B)
3.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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
O6 O 0.4214(2) 0.8815(2) 0.6685(2) 0.0462(6) Uani 1 1 d . . . . .
O1 O 0.8568(3) 0.4543(2) 0.2481(2) 0.0507(6) Uani 1 1 d . . . . .
O2 O 0.6810(2) 0.4878(2) 0.1342(2) 0.0556(6) Uani 1 1 d . . . . .
N3 N 1.0694(3) 0.2567(2) 0.1146(2) 0.0333(6) Uani 1 1 d . . . . .
H3B H 1.006434 0.311823 0.161714 0.040 Uiso 1 1 calc R . . . .
O7 O 0.0544(3) 1.0875(3) 0.7186(2) 0.0569(6) Uani 1 1 d . . . . .
H7A H 0.073632 1.103849 0.785997 0.085 Uiso 1 1 d G . . . .
H7B H -0.014058 1.160102 0.679038 0.085 Uiso 1 1 d G . . . .
O5 O 0.2218(3) 0.9247(3) 0.5697(2) 0.0561(6) Uani 1 1 d . . . . .
H5 H 0.179794 0.973306 0.623440 0.084 Uiso 1 1 calc GR . . . .
N2 N 1.1190(3) 0.1392(2) -0.0551(2) 0.0339(6) Uani 1 1 d . . . . .
N1 N 1.3132(3) 0.1105(2) 0.0683(2) 0.0334(6) Uani 1 1 d . . . . .
O3 O 0.4120(3) 0.5861(3) 0.1387(3) 0.0686(8) Uani 1 1 d D . . . .
N6 N 0.8838(3) 0.2864(3) -0.0043(3) 0.0454(7) Uani 1 1 d . . . . .
H6A H 0.852226 0.269383 -0.065377 0.054 Uiso 1 1 calc R . . . .
H6B H 0.823375 0.342710 0.042789 0.054 Uiso 1 1 calc R . . . .
N5 N 1.3556(3) -0.0064(3) -0.0920(2) 0.0401(6) Uani 1 1 d . . . . .
H5B H 1.326812 -0.026899 -0.152465 0.048 Uiso 1 1 calc R . . . .
H5C H 1.446768 -0.044330 -0.075385 0.048 Uiso 1 1 calc R . . . .
N4 N 1.2575(3) 0.2335(3) 0.2284(3) 0.0518(7) Uani 1 1 d . . . . .
H4A H 1.349301 0.198748 0.243703 0.062 Uiso 1 1 calc R . . . .
H4B H 1.193602 0.290804 0.272779 0.062 Uiso 1 1 calc R . . . .
O4 O 0.2177(3) 0.6939(3) 0.2644(3) 0.0787(8) Uani 1 1 d . . . . .
C11 C 1.2599(3) 0.0834(3) -0.0246(3) 0.0299(6) Uani 1 1 d . . . . .
C12 C 1.0236(3) 0.2268(3) 0.0170(3) 0.0304(6) Uani 1 1 d . . . . .
C7 C 0.7254(3) 0.5106(3) 0.2246(3) 0.0324(6) Uani 1 1 d . . . . .
C2 C 0.4594(3) 0.6682(3) 0.3132(3) 0.0315(6) Uani 1 1 d . . . . .
C4 C 0.4525(3) 0.7812(3) 0.4856(3) 0.0327(6) Uani 1 1 d . . . . .
C3 C 0.3817(3) 0.7524(3) 0.4015(3) 0.0324(6) Uani 1 1 d . . . . .
H3A H 0.277505 0.791241 0.404516 0.039 Uiso 1 1 calc R . . . .
C10 C 1.2148(3) 0.1990(3) 0.1370(3) 0.0317(6) Uani 1 1 d . . . . .
C1 C 0.6183(3) 0.6095(3) 0.3095(3) 0.0305(6) Uani 1 1 d . . . . .
C9 C 0.3647(4) 0.8673(3) 0.5838(3) 0.0356(7) Uani 1 1 d . . . . .
O8 O 1.0660(4) 0.3980(4) 0.4085(4) 0.0948(10) Uani 1 1 d D . . . .
H8A H 0.987045 0.418953 0.383510 0.142 Uiso 1 1 d G . . . .
H8B H 1.084732 0.464200 0.425408 0.142 Uiso 1 1 d DG . . . .
C6 C 0.6870(3) 0.6428(3) 0.3915(3) 0.0373(7) Uani 1 1 d . . . . .
H6 H 0.791727 0.607241 0.387439 0.045 Uiso 1 1 calc R . . . .
C5 C 0.6072(3) 0.7262(3) 0.4789(3) 0.0375(7) Uani 1 1 d . . . . .
H5A H 0.657659 0.745066 0.532985 0.045 Uiso 1 1 calc R . . . .
C8 C 0.3567(4) 0.6484(4) 0.2357(3) 0.0463(8) Uani 1 1 d . . . . .
H3 H 0.508(3) 0.552(7) 0.114(7) 0.20(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 C9 1.217(3) . ?
O1 C7 1.239(3) . ?
O2 C7 1.244(3) . ?
N3 H3B 0.8600 . ?
N3 C12 1.364(3) . ?
N3 C10 1.357(3) . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8502 . ?
O5 H5 0.8200 . ?
O5 C9 1.313(3) . ?
N2 C11 1.345(3) . ?
N2 C12 1.335(3) . ?
N1 C11 1.347(3) . ?
N1 C10 1.329(3) . ?
O3 C8 1.286(4) . ?
O3 H3 0.86(2) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C12 1.307(3) . ?
N5 H5B 0.8600 . ?
N5 H5C 0.8600 . ?
N5 C11 1.321(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C10 1.318(3) . ?
O4 C8 1.226(4) . ?
C7 C1 1.529(4) . ?
C2 C3 1.387(4) . ?
C2 C1 1.419(4) . ?
C2 C8 1.517(4) . ?
C4 C3 1.391(3) . ?
C4 C9 1.492(4) . ?
C4 C5 1.376(4) . ?
C3 H3A 0.9300 . ?
C1 C6 1.386(4) . ?
O8 H8A 0.7952 . ?
O8 H8B 0.8181 . ?
C6 H6 0.9300 . ?
C6 C5 1.378(4) . ?
C5 H5A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N3 H3B 120.1 . . ?
C10 N3 H3B 120.1 . . ?
C10 N3 C12 119.7(2) . . ?
H7A O7 H7B 109.5 . . ?
C9 O5 H5 109.5 . . ?
C12 N2 C11 116.0(2) . . ?
C10 N1 C11 115.9(2) . . ?
C8 O3 H3 123(4) . . ?
H6A N6 H6B 120.0 . . ?
C12 N6 H6A 120.0 . . ?
C12 N6 H6B 120.0 . . ?
H5B N5 H5C 120.0 . . ?
C11 N5 H5B 120.0 . . ?
C11 N5 H5C 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C10 N4 H4A 120.0 . . ?
C10 N4 H4B 120.0 . . ?
N2 C11 N1 126.1(2) . . ?
N5 C11 N2 117.2(2) . . ?
N5 C11 N1 116.6(2) . . ?
N2 C12 N3 120.9(2) . . ?
N6 C12 N3 118.3(2) . . ?
N6 C12 N2 120.9(2) . . ?
O1 C7 O2 121.3(3) . . ?
O1 C7 C1 118.3(2) . . ?
O2 C7 C1 120.4(2) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 C8 113.2(3) . . ?
C1 C2 C8 128.7(2) . . ?
C3 C4 C9 121.7(3) . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 C9 119.7(2) . . ?
C2 C3 C4 122.9(3) . . ?
C2 C3 H3A 118.5 . . ?
C4 C3 H3A 118.5 . . ?
N1 C10 N3 121.4(2) . . ?
N4 C10 N3 118.5(3) . . ?
N4 C10 N1 120.1(3) . . ?
C2 C1 C7 127.2(2) . . ?
C6 C1 C7 114.9(3) . . ?
C6 C1 C2 117.9(2) . . ?
O6 C9 O5 124.0(3) . . ?
O6 C9 C4 122.6(3) . . ?
O5 C9 C4 113.3(2) . . ?
H8A O8 H8B 115.3 . . ?
C1 C6 H6 118.5 . . ?
C5 C6 C1 123.0(3) . . ?
C5 C6 H6 118.5 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
O3 C8 C2 121.6(3) . . ?
O4 C8 O3 118.8(3) . . ?
O4 C8 C2 119.7(3) . . ?

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
O1 C7 C1 C2 -171.6(3) . . . . ?
O1 C7 C1 C6 8.0(3) . . . . ?
O2 C7 C1 C2 8.4(4) . . . . ?
O2 C7 C1 C6 -172.0(2) . . . . ?
C11 N2 C12 N3 0.3(4) . . . . ?
C11 N2 C12 N6 -179.8(2) . . . . ?
C11 N1 C10 N3 0.5(4) . . . . ?
C11 N1 C10 N4 -179.1(2) . . . . ?
C12 N3 C10 N1 -1.6(4) . . . . ?
C12 N3 C10 N4 178.0(2) . . . . ?
C12 N2 C11 N1 -1.5(4) . . . . ?
C12 N2 C11 N5 178.6(2) . . . . ?
C7 C1 C6 C5 -177.8(2) . . . . ?
C2 C1 C6 C5 1.8(4) . . . . ?
C3 C2 C1 C7 178.1(2) . . . . ?
C3 C2 C1 C6 -1.5(4) . . . . ?
C3 C2 C8 O3 173.4(3) . . . . ?
C3 C2 C8 O4 -5.9(4) . . . . ?
C3 C4 C9 O6 173.1(3) . . . . ?
C3 C4 C9 O5 -6.6(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C10 N3 C12 N2 1.2(4) . . . . ?
C10 N3 C12 N6 -178.7(2) . . . . ?
C10 N1 C11 N2 1.1(4) . . . . ?
C10 N1 C11 N5 -179.0(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C2 C8 O3 -8.5(5) . . . . ?
C1 C2 C8 O4 172.2(3) . . . . ?
C1 C6 C5 C4 -0.6(4) . . . . ?
C9 C4 C3 C2 -177.8(2) . . . . ?
C9 C4 C5 C6 178.1(2) . . . . ?
C5 C4 C3 C2 1.2(4) . . . . ?
C5 C4 C9 O6 -5.9(4) . . . . ?
C5 C4 C9 O5 174.4(3) . . . . ?
C8 C2 C3 C4 178.3(2) . . . . ?
C8 C2 C1 C7 0.1(4) . . . . ?
C8 C2 C1 C6 -179.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# 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_20180615b
_database_code_depnum_ccdc_archive 'CCDC 1875919'
loop_
_audit_author_name
_audit_author_address
'Bo Zhou'
;Beijing normal university
China
;
_audit_update_record             
;
2018-12-19 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;
_audit_creation_date             2018-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C9 H5 O6), 2(C3 H7 N6), 4(H2 O)'
_chemical_formula_sum            'C24 H32 N12 O16'
_chemical_formula_weight         744.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1N1
_chemical_oxdiff_usercomment     ZB-5202
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                   9.4813(8)
_cell_length_b                   11.8746(10)
_cell_length_c                   14.6779(13)
_cell_angle_alpha                72.186(7)
_cell_angle_beta                 82.829(7)
_cell_angle_gamma                81.819(7)
_cell_volume                     1551.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2747
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.6040
_cell_measurement_theta_min      3.8550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11545
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.472
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  28.00   1.00   10.00    --  -11.20 -99.00-180.00   37
  2  ω    -56.00  36.00   1.00   10.00    --   12.45 -57.00  30.00   92
  3  ω    -11.00  70.00   1.00   10.00    --   12.45  57.00 -30.00   81
  4  ω    -16.00  85.00   1.00   10.00    --   12.45  57.00-180.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0340613000
_diffrn_orient_matrix_UB_12      -0.0454008000
_diffrn_orient_matrix_UB_13      0.0356076000
_diffrn_orient_matrix_UB_21      -0.0590828000
_diffrn_orient_matrix_UB_22      0.0112676000
_diffrn_orient_matrix_UB_23      -0.0279995000
_diffrn_orient_matrix_UB_31      0.0332292000
_diffrn_orient_matrix_UB_32      -0.0423863000
_diffrn_orient_matrix_UB_33      -0.0233199000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3803
_reflns_number_total             6251
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6251
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.023
_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)+(0.0581P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1489
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O8-H8 = O2-H2
 0.85 with sigma of 0.02
3.a Free rotating group:
 O13(H13A,H13B), O14(H14A,H14B), O15(H15A,H15B), O16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C12(H12), C13(H13), C15(H15), N5(H5), N12(H12B)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N7(H7A,H7B), N8(H8A,H8B), N9(H9A,H9B)
3.d Idealised tetrahedral OH refined as rotating group:
 O6(H6A), O12(H12A)
;
_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 0.1870(2) 0.2545(2) 0.19240(17) 0.0283(5) Uani 1 1 d . . . . .
C2 C 0.1092(2) 0.2637(2) 0.11295(17) 0.0291(6) Uani 1 1 d . . . . .
C3 C 0.1246(3) 0.3612(2) 0.03216(19) 0.0433(7) Uani 1 1 d . . . . .
H3 H 0.074853 0.368095 -0.020348 0.052 Uiso 1 1 calc R . . . .
C4 C 0.2096(3) 0.4475(2) 0.02631(19) 0.0436(7) Uani 1 1 d . . . . .
H4 H 0.215393 0.511913 -0.028778 0.052 Uiso 1 1 calc R . . . .
C5 C 0.2869(3) 0.4385(2) 0.10254(17) 0.0311(6) Uani 1 1 d . . . . .
C6 C 0.2745(2) 0.34280(19) 0.18374(17) 0.0291(6) Uani 1 1 d . . . . .
H6 H 0.326767 0.336867 0.234904 0.035 Uiso 1 1 calc R . . . .
C7 C 0.1901(3) 0.1595(2) 0.28924(18) 0.0351(6) Uani 1 1 d . . . . .
C8 C 0.0131(3) 0.1768(2) 0.10423(18) 0.0309(6) Uani 1 1 d . . . . .
C9 C 0.3778(3) 0.5337(2) 0.09614(19) 0.0357(6) Uani 1 1 d . . . . .
C10 C 0.8523(2) 0.6327(2) 0.46265(17) 0.0293(6) Uani 1 1 d . . . . .
C11 C 0.9127(2) 0.6286(2) 0.54777(17) 0.0285(5) Uani 1 1 d . . . . .
C12 C 0.8755(3) 0.5415(2) 0.63191(18) 0.0343(6) Uani 1 1 d . . . . .
H12 H 0.912510 0.539616 0.688201 0.041 Uiso 1 1 calc R . . . .
C13 C 0.7867(3) 0.4583(2) 0.63569(18) 0.0352(6) Uani 1 1 d . . . . .
H13 H 0.764232 0.401677 0.693563 0.042 Uiso 1 1 calc R . . . .
C14 C 0.7308(2) 0.4590(2) 0.55272(17) 0.0301(6) Uani 1 1 d . . . . .
C15 C 0.7636(3) 0.5462(2) 0.46841(18) 0.0321(6) Uani 1 1 d . . . . .
H15 H 0.724746 0.547121 0.413013 0.039 Uiso 1 1 calc R . . . .
C16 C 0.8684(3) 0.7202(2) 0.36345(19) 0.0419(7) Uani 1 1 d . . . . .
C17 C 1.0173(3) 0.7100(2) 0.55763(19) 0.0339(6) Uani 1 1 d . . . . .
C18 C 0.6374(3) 0.3665(2) 0.5561(2) 0.0362(6) Uani 1 1 d . . . . .
C19 C 0.7664(2) 0.9459(2) 0.05947(17) 0.0292(6) Uani 1 1 d . . . . .
C20 C 0.6224(2) 0.9025(2) -0.03536(17) 0.0289(5) Uani 1 1 d . . . . .
C21 C 0.7368(3) 1.0682(2) -0.09835(18) 0.0336(6) Uani 1 1 d . . . . .
C22 C 0.2816(3) -0.0625(2) 0.59565(17) 0.0323(6) Uani 1 1 d . . . . .
C23 C 0.4174(3) -0.0175(2) 0.69411(17) 0.0307(6) Uani 1 1 d . . . . .
C24 C 0.3194(3) -0.1929(2) 0.74984(18) 0.0316(6) Uani 1 1 d . . . . .
N1 N 0.7675(3) 1.16283(19) -0.16809(16) 0.0513(7) Uani 1 1 d . . . . .
H1A H 0.731077 1.179086 -0.222049 0.062 Uiso 1 1 calc R . . . .
H1B H 0.824179 1.208796 -0.160009 0.062 Uiso 1 1 calc R . . . .
N2 N 0.8274(2) 0.92366(18) 0.13916(14) 0.0387(5) Uani 1 1 d . . . . .
H2A H 0.811454 0.861138 0.185920 0.046 Uiso 1 1 calc R . . . .
H2B H 0.883571 0.971554 0.144812 0.046 Uiso 1 1 calc R . . . .
N3 N 0.5302(2) 0.83442(17) -0.04636(15) 0.0370(5) Uani 1 1 d . . . . .
H3A H 0.508333 0.773218 0.000031 0.044 Uiso 1 1 calc R . . . .
H3B H 0.492318 0.851479 -0.099879 0.044 Uiso 1 1 calc R . . . .
N4 N 0.6495(2) 0.99760(17) -0.11094(14) 0.0352(5) Uani 1 1 d . . . . .
N5 N 0.7951(2) 1.04512(17) -0.01339(14) 0.0319(5) Uani 1 1 d . . . . .
H5 H 0.849789 1.092915 -0.005827 0.038 Uiso 1 1 calc R . . . .
N6 N 0.6790(2) 0.87229(17) 0.04970(14) 0.0326(5) Uani 1 1 d . . . . .
N7 N 0.2228(2) -0.04000(19) 0.51468(16) 0.0474(6) Uani 1 1 d . . . . .
H7A H 0.236035 0.024474 0.469337 0.057 Uiso 1 1 calc R . . . .
H7B H 0.170983 -0.089713 0.506988 0.057 Uiso 1 1 calc R . . . .
N8 N 0.4954(2) 0.05626(18) 0.70985(16) 0.0452(6) Uani 1 1 d . . . . .
H8A H 0.509644 0.121977 0.666271 0.054 Uiso 1 1 calc R . . . .
H8B H 0.532198 0.038953 0.763769 0.054 Uiso 1 1 calc R . . . .
N9 N 0.2970(2) -0.29370(18) 0.81528(15) 0.0424(6) Uani 1 1 d . . . . .
H9A H 0.333894 -0.312286 0.869269 0.051 Uiso 1 1 calc R . . . .
H9B H 0.245286 -0.341231 0.804219 0.051 Uiso 1 1 calc R . . . .
N10 N 0.3621(2) 0.01346(17) 0.60875(14) 0.0360(5) Uani 1 1 d . . . . .
N11 N 0.3989(2) -0.11932(17) 0.76643(14) 0.0343(5) Uani 1 1 d . . . . .
N12 N 0.2577(2) -0.16523(17) 0.66534(14) 0.0329(5) Uani 1 1 d . . . . .
H12B H 0.203923 -0.212691 0.656324 0.039 Uiso 1 1 calc R . . . .
O1 O 0.2613(2) 0.16977(15) 0.35005(13) 0.0464(5) Uani 1 1 d . . . . .
O2 O 0.1199(2) 0.06872(16) 0.30870(13) 0.0518(6) Uani 1 1 d D . . . .
O3 O -0.0097(2) 0.08531(15) 0.17293(13) 0.0480(5) Uani 1 1 d . . . . .
O4 O -0.0411(2) 0.19719(16) 0.02684(13) 0.0470(5) Uani 1 1 d . . . . .
O5 O 0.3915(2) 0.61826(16) 0.02562(13) 0.0474(5) Uani 1 1 d . . . . .
O6 O 0.4398(2) 0.51550(16) 0.17527(13) 0.0510(5) Uani 1 1 d . . . . .
H6A H 0.481712 0.572957 0.171031 0.077 Uiso 1 1 calc GR . . . .
O7 O 0.8067(3) 0.70865(19) 0.29903(15) 0.0752(7) Uani 1 1 d . . . . .
O8 O 0.9461(2) 0.80525(18) 0.34499(14) 0.0585(6) Uani 1 1 d D . . . .
O9 O 1.0511(2) 0.79582(17) 0.48770(14) 0.0566(6) Uani 1 1 d . . . . .
O10 O 1.06894(19) 0.68733(15) 0.63613(13) 0.0436(5) Uani 1 1 d . . . . .
O11 O 0.6039(2) 0.29119(17) 0.62971(14) 0.0544(5) Uani 1 1 d . . . . .
O12 O 0.5966(2) 0.37548(16) 0.47192(13) 0.0480(5) Uani 1 1 d . . . . .
H12A H 0.552620 0.319154 0.476257 0.072 Uiso 1 1 calc GR . . . .
O13 O 0.4473(2) 0.21494(16) 0.46376(14) 0.0483(5) Uani 1 1 d . . . . .
H13A H 0.417381 0.154700 0.506373 0.072 Uiso 1 1 d G . . . .
H13B H 0.392520 0.229297 0.418936 0.072 Uiso 1 1 d G . . . .
O14 O 0.5828(3) 0.67626(17) 0.19185(15) 0.0570(6) Uani 1 1 d . . . . .
H14A H 0.620387 0.736851 0.155187 0.086 Uiso 1 1 d G . . . .
H14B H 0.564918 0.690411 0.245731 0.086 Uiso 1 1 d G . . . .
O15 O -0.0704(2) 0.3357(2) -0.15829(16) 0.0649(6) Uani 1 1 d . . . . .
H15A H 0.008084 0.360818 -0.186056 0.097 Uiso 1 1 d G . . . .
H15B H -0.055355 0.307780 -0.099265 0.097 Uiso 1 1 d G . . . .
O16 O 1.1697(3) 0.5115(2) 0.79145(16) 0.0735(7) Uani 1 1 d . . . . .
H16A H 1.227941 0.459444 0.773544 0.110 Uiso 1 1 d G . . . .
H16B H 1.124198 0.548109 0.742606 0.110 Uiso 1 1 d G . . . .
H2 H 0.064(3) 0.077(3) 0.262(2) 0.086(12) Uiso 1 1 d D . . . .
H8 H 0.987(3) 0.805(3) 0.3942(19) 0.092(13) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.425(3) . ?
C1 C6 1.394(3) . ?
C1 C7 1.521(3) . ?
C2 C3 1.390(3) . ?
C2 C8 1.514(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 C6 1.378(3) . ?
C5 C9 1.490(3) . ?
C6 H6 0.9300 . ?
C7 O1 1.228(3) . ?
C7 O2 1.286(3) . ?
C8 O3 1.259(3) . ?
C8 O4 1.247(3) . ?
C9 O5 1.210(3) . ?
C9 O6 1.312(3) . ?
C10 C11 1.423(3) . ?
C10 C15 1.394(3) . ?
C10 C16 1.513(3) . ?
C11 C12 1.390(3) . ?
C11 C17 1.527(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(3) . ?
C14 C15 1.382(3) . ?
C14 C18 1.493(3) . ?
C15 H15 0.9300 . ?
C16 O7 1.223(3) . ?
C16 O8 1.276(3) . ?
C17 O9 1.251(3) . ?
C17 O10 1.246(3) . ?
C18 O11 1.213(3) . ?
C18 O12 1.309(3) . ?
C19 N2 1.307(3) . ?
C19 N5 1.361(3) . ?
C19 N6 1.336(3) . ?
C20 N3 1.326(3) . ?
C20 N4 1.348(3) . ?
C20 N6 1.347(3) . ?
C21 N1 1.308(3) . ?
C21 N4 1.324(3) . ?
C21 N5 1.363(3) . ?
C22 N7 1.313(3) . ?
C22 N10 1.331(3) . ?
C22 N12 1.357(3) . ?
C23 N8 1.311(3) . ?
C23 N10 1.344(3) . ?
C23 N11 1.359(3) . ?
C24 N9 1.311(3) . ?
C24 N11 1.325(3) . ?
C24 N12 1.366(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N5 H5 0.8600 . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N12 H12B 0.8600 . ?
O2 H2 0.887(18) . ?
O6 H6A 0.8200 . ?
O8 H8 0.865(18) . ?
O12 H12A 0.8200 . ?
O13 H13A 0.8503 . ?
O13 H13B 0.8502 . ?
O14 H14A 0.8501 . ?
O14 H14B 0.8498 . ?
O15 H15A 0.8498 . ?
O15 H15B 0.8501 . ?
O16 H16A 0.8496 . ?
O16 H16B 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
C2 C1 C7 129.2(2) . . ?
C6 C1 C2 118.0(2) . . ?
C6 C1 C7 112.8(2) . . ?
C1 C2 C8 127.4(2) . . ?
C3 C2 C1 117.6(2) . . ?
C3 C2 C8 114.9(2) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 C2 123.1(2) . . ?
C4 C3 H3 118.5 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C9 119.5(2) . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 C9 121.8(2) . . ?
C1 C6 H6 118.6 . . ?
C5 C6 C1 122.8(2) . . ?
C5 C6 H6 118.6 . . ?
O1 C7 C1 119.2(2) . . ?
O1 C7 O2 119.4(2) . . ?
O2 C7 C1 121.4(2) . . ?
O3 C8 C2 120.8(2) . . ?
O4 C8 C2 118.3(2) . . ?
O4 C8 O3 121.0(2) . . ?
O5 C9 C5 123.2(2) . . ?
O5 C9 O6 124.3(2) . . ?
O6 C9 C5 112.5(2) . . ?
C11 C10 C16 129.1(2) . . ?
C15 C10 C11 117.7(2) . . ?
C15 C10 C16 113.1(2) . . ?
C10 C11 C17 127.0(2) . . ?
C12 C11 C10 118.0(2) . . ?
C12 C11 C17 115.1(2) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 C11 123.0(2) . . ?
C13 C12 H12 118.5 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C18 119.6(2) . . ?
C15 C14 C13 118.7(2) . . ?
C15 C14 C18 121.6(2) . . ?
C10 C15 H15 118.5 . . ?
C14 C15 C10 123.0(2) . . ?
C14 C15 H15 118.5 . . ?
O7 C16 C10 119.2(2) . . ?
O7 C16 O8 119.1(3) . . ?
O8 C16 C10 121.7(2) . . ?
O9 C17 C11 120.2(2) . . ?
O10 C17 C11 118.3(2) . . ?
O10 C17 O9 121.5(2) . . ?
O11 C18 C14 122.8(2) . . ?
O11 C18 O12 124.3(2) . . ?
O12 C18 C14 113.0(2) . . ?
N2 C19 N5 118.4(2) . . ?
N2 C19 N6 120.6(2) . . ?
N6 C19 N5 120.9(2) . . ?
N3 C20 N4 116.4(2) . . ?
N3 C20 N6 117.9(2) . . ?
N6 C20 N4 125.7(2) . . ?
N1 C21 N4 119.9(2) . . ?
N1 C21 N5 118.8(2) . . ?
N4 C21 N5 121.3(2) . . ?
N7 C22 N10 120.8(2) . . ?
N7 C22 N12 118.0(2) . . ?
N10 C22 N12 121.2(2) . . ?
N8 C23 N10 117.8(2) . . ?
N8 C23 N11 116.7(2) . . ?
N10 C23 N11 125.5(2) . . ?
N9 C24 N11 120.3(2) . . ?
N9 C24 N12 118.6(2) . . ?
N11 C24 N12 121.1(2) . . ?
C21 N1 H1A 120.0 . . ?
C21 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C19 N2 H2A 120.0 . . ?
C19 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C20 N3 H3A 120.0 . . ?
C20 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C21 N4 C20 116.3(2) . . ?
C19 N5 C21 119.6(2) . . ?
C19 N5 H5 120.2 . . ?
C21 N5 H5 120.2 . . ?
C19 N6 C20 116.1(2) . . ?
C22 N7 H7A 120.0 . . ?
C22 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C23 N8 H8A 120.0 . . ?
C23 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C24 N9 H9A 120.0 . . ?
C24 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C22 N10 C23 116.3(2) . . ?
C24 N11 C23 116.1(2) . . ?
C22 N12 C24 119.8(2) . . ?
C22 N12 H12B 120.1 . . ?
C24 N12 H12B 120.1 . . ?
C7 O2 H2 110(2) . . ?
C9 O6 H6A 109.5 . . ?
C16 O8 H8 113(2) . . ?
C18 O12 H12A 109.5 . . ?
H13A O13 H13B 104.5 . . ?
H14A O14 H14B 104.5 . . ?
H15A O15 H15B 104.5 . . ?
H16A O16 H16B 104.5 . . ?

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
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C8 O3 2.4(4) . . . . ?
C1 C2 C8 O4 -176.6(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C2 C1 C7 O1 -177.6(2) . . . . ?
C2 C1 C7 O2 2.4(4) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C2 C8 O3 -179.6(2) . . . . ?
C3 C2 C8 O4 1.4(3) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C3 C4 C5 C9 -179.2(2) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C9 O5 -2.3(4) . . . . ?
C4 C5 C9 O6 177.3(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C1 C2 C8 177.3(2) . . . . ?
C6 C1 C7 O1 2.6(3) . . . . ?
C6 C1 C7 O2 -177.4(2) . . . . ?
C6 C5 C9 O5 179.5(2) . . . . ?
C6 C5 C9 O6 -0.9(3) . . . . ?
C7 C1 C2 C3 179.5(2) . . . . ?
C7 C1 C2 C8 -2.6(4) . . . . ?
C7 C1 C6 C5 -179.2(2) . . . . ?
C8 C2 C3 C4 -178.6(2) . . . . ?
C9 C5 C6 C1 178.1(2) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C10 C11 C17 O9 5.0(4) . . . . ?
C10 C11 C17 O10 -174.0(2) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
C11 C10 C16 O7 -179.8(3) . . . . ?
C11 C10 C16 O8 0.9(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C11 C17 O9 -175.6(2) . . . . ?
C12 C11 C17 O10 5.4(3) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C12 C13 C14 C18 178.3(2) . . . . ?
C13 C14 C15 C10 0.9(4) . . . . ?
C13 C14 C18 O11 2.3(4) . . . . ?
C13 C14 C18 O12 -177.6(2) . . . . ?
C15 C10 C11 C12 -2.3(3) . . . . ?
C15 C10 C11 C17 177.1(2) . . . . ?
C15 C10 C16 O7 -0.5(4) . . . . ?
C15 C10 C16 O8 -179.8(2) . . . . ?
C15 C14 C18 O11 -177.9(2) . . . . ?
C15 C14 C18 O12 2.2(3) . . . . ?
C16 C10 C11 C12 176.9(2) . . . . ?
C16 C10 C11 C17 -3.7(4) . . . . ?
C16 C10 C15 C14 -178.3(2) . . . . ?
C17 C11 C12 C13 -177.7(2) . . . . ?
C18 C14 C15 C10 -179.0(2) . . . . ?
N1 C21 N4 C20 -179.5(2) . . . . ?
N1 C21 N5 C19 -178.8(2) . . . . ?
N2 C19 N5 C21 177.8(2) . . . . ?
N2 C19 N6 C20 -179.5(2) . . . . ?
N3 C20 N4 C21 177.2(2) . . . . ?
N3 C20 N6 C19 -177.1(2) . . . . ?
N4 C20 N6 C19 1.9(3) . . . . ?
N4 C21 N5 C19 1.7(4) . . . . ?
N5 C19 N6 C20 -0.1(3) . . . . ?
N5 C21 N4 C20 0.0(3) . . . . ?
N6 C19 N5 C21 -1.6(3) . . . . ?
N6 C20 N4 C21 -1.9(3) . . . . ?
N7 C22 N10 C23 179.9(2) . . . . ?
N7 C22 N12 C24 178.7(2) . . . . ?
N8 C23 N10 C22 -179.0(2) . . . . ?
N8 C23 N11 C24 179.7(2) . . . . ?
N9 C24 N11 C23 179.4(2) . . . . ?
N9 C24 N12 C22 -178.7(2) . . . . ?
N10 C22 N12 C24 -1.4(4) . . . . ?
N10 C23 N11 C24 0.0(4) . . . . ?
N11 C23 N10 C22 0.7(4) . . . . ?
N11 C24 N12 C22 2.2(4) . . . . ?
N12 C22 N10 C23 0.0(3) . . . . ?
N12 C24 N11 C23 -1.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.798
