# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ZGF230606
_database_code_depnum_ccdc_archive 'CCDC 2353053'
loop_
_audit_author_name
_audit_author_address
'Guofeng Zhang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-04 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 K2 N12 O3'
_chemical_formula_sum            'C4 H2 K2 N12 O3'
_chemical_formula_weight         344.38

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.6026(9)
_cell_length_b                   13.5204(18)
_cell_length_c                   13.4527(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.755(3)
_cell_angle_gamma                90
_cell_volume                     1183.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5934
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      25.06

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.838
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6194
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   twinabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            2734
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.013
_diffrn_reflns_theta_max         27.570
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2734
_reflns_number_gt                1783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²+2.0261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2734
_refine_ls_number_parameters     197
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.1650
_refine_ls_wR_factor_gt          0.1396
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.7411(2) 0.58540(10) 0.90658(10) 0.0316(4) Uani 1 1 d . . . . .
K2 K 0.3125(2) 0.69895(10) 0.62727(12) 0.0425(4) Uani 1 1 d . . . . .
O1 O 0.6756(8) 0.7337(3) 0.7636(3) 0.0423(12) Uani 1 1 d D . . . .
H1A H 0.688(11) 0.793(2) 0.781(5) 0.063 Uiso 1 1 d D U . . .
H1B H 0.732(10) 0.722(4) 0.713(4) 0.063 Uiso 1 1 d D U . . .
C1 C 0.7470(9) 0.5707(4) 0.2901(4) 0.0241(13) Uani 1 1 d . . . . .
C2 C 0.7495(8) 0.5673(4) 0.4432(4) 0.0192(11) Uani 1 1 d . . . . .
C3 C 0.7565(9) 0.5331(4) 0.5443(4) 0.0235(12) Uani 1 1 d . . . . .
C4 C 0.7632(8) 0.7516(4) 0.4699(4) 0.0223(12) Uani 1 1 d . . . . .
N1 N 0.9378(7) 0.7937(4) 0.5096(4) 0.0329(12) Uani 1 1 d . . . . .
N2 N 0.8749(8) 0.8749(4) 0.5557(4) 0.0349(13) Uani 1 1 d . . . . .
N3 N 0.6774(8) 0.8791(4) 0.5423(4) 0.0331(13) Uani 1 1 d . . . . .
N4 N 0.5964(7) 0.7993(4) 0.4879(4) 0.0320(12) Uani 1 1 d . . . . .
N5 N 0.7739(9) 0.5878(4) 0.6282(4) 0.0398(13) Uani 1 1 d . . . . .
N6 N 0.7749(9) 0.5208(4) 0.7025(4) 0.0402(14) Uani 1 1 d . . . . .
N7 N 0.7613(8) 0.4322(4) 0.6641(4) 0.0323(12) Uani 1 1 d . . . . .
N8 N 0.7482(8) 0.4362(3) 0.5646(3) 0.0290(12) Uani 1 1 d . . . . .
N9 N 0.7522(7) 0.6658(3) 0.3111(3) 0.0238(11) Uani 1 1 d . . . . .
N10 N 0.7439(7) 0.5072(3) 0.3656(4) 0.0258(11) Uani 1 1 d . . . . .
N11 N 0.7521(7) 0.6630(3) 0.4115(4) 0.0238(10) Uani 1 1 d . . . . .
N12 N 0.7517(7) 0.5341(4) 0.1890(4) 0.0285(12) Uani 1 1 d . . . . .
O2 O 0.7053(8) 0.4475(3) 0.1737(3) 0.0470(13) Uani 1 1 d . . . . .
O3 O 0.8025(6) 0.5917(3) 0.1282(3) 0.0361(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O1 2.761(5) . ?
K1 N4 2.874(5) 4_676 ?
K1 N3 2.901(5) 2_646 ?
K1 N6 2.925(6) . ?
K1 O3 2.941(4) 1_556 ?
K1 O2 2.996(5) 3_666 ?
K1 N2 3.013(5) 2_646 ?
K1 N1 3.089(5) 4_576 ?
K1 N3 3.175(6) 4_676 ?
K1 N2 3.436(6) 4_576 ?
K1 K2 4.131(2) 4_676 ?
K1 K1 4.519(3) 3_767 ?
K2 O1 2.801(5) . ?
K2 N10 2.815(4) 3_666 ?
K2 O3 2.832(5) 4_576 ?
K2 N1 2.990(5) 1_455 ?
K2 N8 3.132(5) 3_666 ?
K2 N9 3.155(5) 4_576 ?
K2 N4 3.172(5) . ?
K2 O2 3.348(5) 3_666 ?
K2 N5 3.395(6) . ?
K2 H1B 2.83(7) . ?
O1 H1A 0.84(2) . ?
O1 H1B 0.84(2) . ?
C1 N9 1.315(7) . ?
C1 N10 1.333(7) . ?
C1 N12 1.452(7) . ?
C2 N10 1.319(6) . ?
C2 N11 1.364(7) . ?
C2 C3 1.429(7) . ?
C3 N5 1.338(7) . ?
C3 N8 1.342(7) . ?
C4 N1 1.315(7) . ?
C4 N4 1.333(7) . ?
C4 N11 1.428(7) . ?
N1 N2 1.360(7) . ?
N2 N3 1.287(7) . ?
N3 N4 1.362(7) . ?
N5 N6 1.349(7) . ?
N6 N7 1.302(7) . ?
N7 N8 1.328(7) . ?
N9 N11 1.351(6) . ?
N12 O3 1.217(6) . ?
N12 O2 1.219(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 K1 N4 83.85(14) . 4_676 ?
O1 K1 N3 149.77(14) . 2_646 ?
N4 K1 N3 108.95(14) 4_676 2_646 ?
O1 K1 N6 65.86(14) . . ?
N4 K1 N6 109.41(16) 4_676 . ?
N3 K1 N6 83.95(15) 2_646 . ?
O1 K1 O3 131.57(13) . 1_556 ?
N4 K1 O3 68.60(13) 4_676 1_556 ?
N3 K1 O3 78.43(14) 2_646 1_556 ?
N6 K1 O3 160.16(15) . 1_556 ?
O1 K1 O2 80.10(14) . 3_666 ?
N4 K1 O2 155.16(14) 4_676 3_666 ?
N3 K1 O2 94.27(14) 2_646 3_666 ?
N6 K1 O2 81.03(15) . 3_666 ?
O3 K1 O2 109.13(13) 1_556 3_666 ?
O1 K1 N2 142.08(14) . 2_646 ?
N4 K1 N2 131.51(14) 4_676 2_646 ?
N3 K1 N2 25.05(14) 2_646 2_646 ?
N6 K1 N2 86.44(15) . 2_646 ?
O3 K1 N2 81.48(14) 1_556 2_646 ?
O2 K1 N2 69.99(13) 3_666 2_646 ?
O1 K1 N1 83.75(13) . 4_576 ?
N4 K1 N1 95.26(14) 4_676 4_576 ?
N3 K1 N1 120.71(14) 2_646 4_576 ?
N6 K1 N1 137.49(15) . 4_576 ?
O3 K1 N1 61.21(13) 1_556 4_576 ?
O2 K1 N1 64.34(13) 3_666 4_576 ?
N2 K1 N1 102.80(14) 2_646 4_576 ?
O1 K1 N3 108.11(14) . 4_676 ?
N4 K1 N3 25.40(13) 4_676 4_676 ?
N3 K1 N3 83.99(15) 2_646 4_676 ?
N6 K1 N3 112.28(15) . 4_676 ?
O3 K1 N3 57.10(13) 1_556 4_676 ?
O2 K1 N3 166.21(13) 3_666 4_676 ?
N2 K1 N3 106.13(14) 2_646 4_676 ?
N1 K1 N3 104.83(14) 4_576 4_676 ?
O1 K1 N2 104.50(13) . 4_576 ?
N4 K1 N2 107.62(14) 4_676 4_576 ?
N3 K1 N2 97.62(14) 2_646 4_576 ?
N6 K1 N2 140.15(15) . 4_576 ?
O3 K1 N2 52.64(13) 1_556 4_576 ?
O2 K1 N2 59.12(12) 3_666 4_576 ?
N2 K1 N2 79.93(15) 2_646 4_576 ?
N1 K1 N2 23.29(12) 4_576 4_576 ?
N3 K1 N2 107.46(13) 4_676 4_576 ?
O1 K1 K2 88.47(10) . 4_676 ?
N4 K1 K2 50.00(10) 4_676 4_676 ?
N3 K1 K2 120.96(11) 2_646 4_676 ?
N6 K1 K2 150.20(12) . 4_676 ?
O3 K1 K2 43.27(9) 1_556 4_676 ?
O2 K1 K2 110.44(9) 3_666 4_676 ?
N2 K1 K2 123.17(11) 2_646 4_676 ?
N1 K1 K2 46.20(10) 4_576 4_676 ?
N3 K1 K2 59.87(10) 4_676 4_676 ?
N2 K1 K2 58.39(9) 4_576 4_676 ?
O1 K1 K1 140.62(12) . 3_767 ?
N4 K1 K1 64.78(10) 4_676 3_767 ?
N3 K1 K1 44.32(11) 2_646 3_767 ?
N6 K1 K1 101.46(12) . 3_767 ?
O3 K1 K1 59.31(9) 1_556 3_767 ?
O2 K1 K1 136.89(10) 3_666 3_767 ?
N2 K1 K1 67.27(10) 2_646 3_767 ?
N1 K1 K1 120.51(10) 4_576 3_767 ?
N3 K1 K1 39.67(9) 4_676 3_767 ?
N2 K1 K1 107.21(10) 4_576 3_767 ?
K2 K1 K1 88.71(4) 4_676 3_767 ?
O1 K2 N10 104.31(14) . 3_666 ?
O1 K2 O3 81.23(12) . 4_576 ?
N10 K2 O3 170.44(14) 3_666 4_576 ?
O1 K2 N1 144.54(13) . 1_455 ?
N10 K2 N1 109.88(14) 3_666 1_455 ?
O3 K2 N1 63.65(13) 4_576 1_455 ?
O1 K2 N8 127.84(14) . 3_666 ?
N10 K2 N8 56.73(14) 3_666 3_666 ?
O3 K2 N8 125.94(13) 4_576 3_666 ?
N1 K2 N8 80.49(13) 1_455 3_666 ?
O1 K2 N9 66.23(12) . 4_576 ?
N10 K2 N9 120.82(14) 3_666 4_576 ?
O3 K2 N9 53.90(12) 4_576 4_576 ?
N1 K2 N9 87.92(13) 1_455 4_576 ?
N8 K2 N9 165.62(13) 3_666 4_576 ?
O1 K2 N4 77.83(14) . . ?
N10 K2 N4 122.56(14) 3_666 . ?
O3 K2 N4 65.90(12) 4_576 . ?
N1 K2 N4 91.30(14) 1_455 . ?
N8 K2 N4 76.60(13) 3_666 . ?
N9 K2 N4 112.39(12) 4_576 . ?
O1 K2 O2 73.59(13) . 3_666 ?
N10 K2 O2 50.56(13) 3_666 3_666 ?
O3 K2 O2 125.71(12) 4_576 3_666 ?
N1 K2 O2 122.61(15) 1_455 3_666 ?
N8 K2 O2 107.29(12) 3_666 3_666 ?
N9 K2 O2 71.93(12) 4_576 3_666 ?
N4 K2 O2 146.09(14) . 3_666 ?
O1 K2 N5 53.40(13) . . ?
N10 K2 N5 71.67(13) 3_666 . ?
O3 K2 N5 117.64(13) 4_576 . ?
N1 K2 N5 148.53(14) 1_455 . ?
N8 K2 N5 74.59(13) 3_666 . ?
N9 K2 N5 119.07(12) 4_576 . ?
N4 K2 N5 64.62(13) . . ?
O2 K2 N5 83.60(12) 3_666 . ?
O1 K2 K1 109.46(10) . 4_575 ?
N10 K2 K1 136.34(12) 3_666 4_575 ?
O3 K2 K1 45.38(9) 4_576 4_575 ?
N1 K2 K1 48.21(11) 1_455 4_575 ?
N8 K2 K1 80.58(9) 3_666 4_575 ?
N9 K2 K1 98.05(9) 4_576 4_575 ?
N4 K2 K1 43.96(9) . 4_575 ?
O2 K2 K1 167.69(10) 3_666 4_575 ?
N5 K2 K1 107.93(9) . 4_575 ?
O1 K2 K1 34.46(9) . . ?
N10 K2 K1 72.93(11) 3_666 . ?
O3 K2 K1 110.11(10) 4_576 . ?
N1 K2 K1 157.06(11) 1_455 . ?
N8 K2 K1 117.17(9) 3_666 . ?
N9 K2 K1 72.12(9) 4_576 . ?
N4 K2 K1 106.49(10) . . ?
O2 K2 K1 40.93(9) 3_666 . ?
N5 K2 K1 54.41(8) . . ?
K1 K2 K1 143.84(5) 4_575 . ?
O1 K2 H1B 17.2(5) . . ?
N10 K2 H1B 102.7(12) 3_666 . ?
O3 K2 H1B 84.9(12) 4_576 . ?
N1 K2 H1B 146.4(13) 1_455 . ?
N8 K2 H1B 112.3(6) 3_666 . ?
N9 K2 H1B 82.0(6) 4_576 . ?
N4 K2 H1B 63.8(9) . . ?
O2 K2 H1B 84.4(11) 3_666 . ?
N5 K2 H1B 39.8(8) . . ?
K1 K2 H1B 101.6(12) 4_575 . ?
K1 K2 H1B 43.5(11) . . ?
K1 O1 K2 110.50(15) . . ?
K1 O1 H1A 120(5) . . ?
K2 O1 H1A 112(5) . . ?
K1 O1 H1B 113(5) . . ?
K2 O1 H1B 84(5) . . ?
H1A O1 H1B 112(3) . . ?
N9 C1 N10 118.0(5) . . ?
N9 C1 N12 122.0(5) . . ?
N10 C1 N12 119.9(5) . . ?
N10 C2 N11 109.7(5) . . ?
N10 C2 C3 123.1(5) . . ?
N11 C2 C3 127.2(5) . . ?
N5 C3 N8 111.7(5) . . ?
N5 C3 C2 127.4(5) . . ?
N8 C3 C2 120.9(5) . . ?
N1 C4 N4 114.3(5) . . ?
N1 C4 N11 123.1(5) . . ?
N4 C4 N11 122.6(5) . . ?
C4 N1 N2 102.7(5) . . ?
C4 N1 K2 128.2(4) . 1_655 ?
N2 N1 K2 113.2(3) . 1_655 ?
C4 N1 K1 129.6(4) . 4_675 ?
N2 N1 K1 92.8(3) . 4_675 ?
K2 N1 K1 85.59(13) 1_655 4_675 ?
N3 N2 N1 110.6(5) . . ?
N3 N2 K1 72.6(3) . 2_656 ?
N1 N2 K1 160.9(4) . 2_656 ?
N3 N2 K1 135.1(4) . 4_675 ?
N1 N2 K1 63.9(3) . 4_675 ?
K1 N2 K1 100.07(15) 2_656 4_675 ?
N2 N3 N4 109.6(5) . . ?
N2 N3 K1 82.3(3) . 2_656 ?
N4 N3 K1 158.4(4) . 2_656 ?
N2 N3 K1 152.4(4) . 4_575 ?
N4 N3 K1 64.9(3) . 4_575 ?
K1 N3 K1 96.01(15) 2_656 4_575 ?
C4 N4 N3 102.7(4) . . ?
C4 N4 K1 147.0(4) . 4_575 ?
N3 N4 K1 89.7(3) . 4_575 ?
C4 N4 K2 119.3(3) . . ?
N3 N4 K2 103.8(3) . . ?
K1 N4 K2 86.04(13) 4_575 . ?
C3 N5 N6 104.1(5) . . ?
C3 N5 K2 107.0(4) . . ?
N6 N5 K2 101.0(4) . . ?
N7 N6 N5 109.4(5) . . ?
N7 N6 K1 129.5(4) . . ?
N5 N6 K1 120.3(4) . . ?
N6 N7 N8 110.6(4) . . ?
N7 N8 C3 104.2(4) . . ?
N7 N8 K2 141.7(4) . 3_666 ?
C3 N8 K2 114.0(3) . 3_666 ?
C1 N9 N11 100.5(4) . . ?
C1 N9 K2 113.6(3) . 4_675 ?
N11 N9 K2 145.2(3) . 4_675 ?
C2 N10 C1 101.8(4) . . ?
C2 N10 K2 124.7(4) . 3_666 ?
C1 N10 K2 133.1(4) . 3_666 ?
N9 N11 C2 110.0(4) . . ?
N9 N11 C4 121.2(4) . . ?
C2 N11 C4 128.7(5) . . ?
O3 N12 O2 126.2(5) . . ?
O3 N12 C1 117.6(5) . . ?
O2 N12 C1 116.2(5) . . ?
N12 O2 K1 114.0(4) . 3_666 ?
N12 O2 K2 118.3(4) . 3_666 ?
K1 O2 K2 92.00(12) 3_666 3_666 ?
N12 O3 K2 130.7(4) . 4_675 ?
N12 O3 K1 131.1(3) . 1_554 ?
K2 O3 K1 91.35(13) 4_675 1_554 ?

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
N10 C2 C3 N5 176.0(6) . . . . ?
N11 C2 C3 N5 -2.4(10) . . . . ?
N10 C2 C3 N8 -3.1(9) . . . . ?
N11 C2 C3 N8 178.5(6) . . . . ?
N4 C4 N1 N2 -0.4(7) . . . . ?
N11 C4 N1 N2 178.9(5) . . . . ?
N4 C4 N1 K2 133.3(4) . . . 1_655 ?
N11 C4 N1 K2 -47.4(7) . . . 1_655 ?
N4 C4 N1 K1 -105.0(5) . . . 4_675 ?
N11 C4 N1 K1 74.3(6) . . . 4_675 ?
C4 N1 N2 N3 -0.6(7) . . . . ?
K2 N1 N2 N3 -142.4(4) 1_655 . . . ?
K1 N1 N2 N3 131.1(5) 4_675 . . . ?
C4 N1 N2 K1 -97.0(12) . . . 2_656 ?
K2 N1 N2 K1 121.1(11) 1_655 . . 2_656 ?
K1 N1 N2 K1 34.7(12) 4_675 . . 2_656 ?
C4 N1 N2 K1 -131.7(5) . . . 4_675 ?
K2 N1 N2 K1 86.4(2) 1_655 . . 4_675 ?
N1 N2 N3 N4 1.3(7) . . . . ?
K1 N2 N3 N4 161.4(5) 2_656 . . . ?
K1 N2 N3 N4 74.5(6) 4_675 . . . ?
N1 N2 N3 K1 -160.1(5) . . . 2_656 ?
K1 N2 N3 K1 -86.9(4) 4_675 . . 2_656 ?
N1 N2 N3 K1 -71.8(10) . . . 4_575 ?
K1 N2 N3 K1 88.3(8) 2_656 . . 4_575 ?
K1 N2 N3 K1 1.4(12) 4_675 . . 4_575 ?
N1 C4 N4 N3 1.1(6) . . . . ?
N11 C4 N4 N3 -178.2(5) . . . . ?
N1 C4 N4 K1 110.9(7) . . . 4_575 ?
N11 C4 N4 K1 -68.4(8) . . . 4_575 ?
N1 C4 N4 K2 -112.9(5) . . . . ?
N11 C4 N4 K2 67.8(6) . . . . ?
N2 N3 N4 C4 -1.5(6) . . . . ?
K1 N3 N4 C4 119.6(9) 2_656 . . . ?
K1 N3 N4 C4 149.2(4) 4_575 . . . ?
N2 N3 N4 K1 -150.7(5) . . . 4_575 ?
K1 N3 N4 K1 -29.6(10) 2_656 . . 4_575 ?
N2 N3 N4 K2 123.5(4) . . . . ?
K1 N3 N4 K2 -115.5(9) 2_656 . . . ?
K1 N3 N4 K2 -85.86(17) 4_575 . . . ?
N8 C3 N5 N6 -0.4(7) . . . . ?
C2 C3 N5 N6 -179.6(6) . . . . ?
N8 C3 N5 K2 -106.8(5) . . . . ?
C2 C3 N5 K2 74.0(6) . . . . ?
C3 N5 N6 N7 0.7(7) . . . . ?
K2 N5 N6 N7 111.6(5) . . . . ?
C3 N5 N6 K1 -169.9(4) . . . . ?
K2 N5 N6 K1 -59.0(4) . . . . ?
N5 N6 N7 N8 -0.8(7) . . . . ?
K1 N6 N7 N8 168.7(4) . . . . ?
N6 N7 N8 C3 0.5(7) . . . . ?
N6 N7 N8 K2 -175.7(4) . . . 3_666 ?
N5 C3 N8 N7 -0.1(7) . . . . ?
C2 C3 N8 N7 179.2(5) . . . . ?
N5 C3 N8 K2 177.4(4) . . . 3_666 ?
C2 C3 N8 K2 -3.4(7) . . . 3_666 ?
N10 C1 N9 N11 -0.1(7) . . . . ?
N12 C1 N9 N11 -178.0(5) . . . . ?
N10 C1 N9 K2 173.1(4) . . . 4_675 ?
N12 C1 N9 K2 -4.8(6) . . . 4_675 ?
N11 C2 N10 C1 1.0(6) . . . . ?
C3 C2 N10 C1 -177.6(5) . . . . ?
N11 C2 N10 K2 -172.2(3) . . . 3_666 ?
C3 C2 N10 K2 9.2(7) . . . 3_666 ?
N9 C1 N10 C2 -0.6(7) . . . . ?
N12 C1 N10 C2 177.3(5) . . . . ?
N9 C1 N10 K2 171.8(4) . . . 3_666 ?
N12 C1 N10 K2 -10.3(8) . . . 3_666 ?
C1 N9 N11 C2 0.8(6) . . . . ?
K2 N9 N11 C2 -168.2(4) 4_675 . . . ?
C1 N9 N11 C4 178.1(5) . . . . ?
K2 N9 N11 C4 9.1(9) 4_675 . . . ?
N10 C2 N11 N9 -1.2(6) . . . . ?
C3 C2 N11 N9 177.3(5) . . . . ?
N10 C2 N11 C4 -178.3(5) . . . . ?
C3 C2 N11 C4 0.3(9) . . . . ?
N1 C4 N11 N9 -86.9(7) . . . . ?
N4 C4 N11 N9 92.4(7) . . . . ?
N1 C4 N11 C2 89.9(7) . . . . ?
N4 C4 N11 C2 -90.9(7) . . . . ?
N9 C1 N12 O3 14.7(8) . . . . ?
N10 C1 N12 O3 -163.1(5) . . . . ?
N9 C1 N12 O2 -165.9(6) . . . . ?
N10 C1 N12 O2 16.3(8) . . . . ?
O3 N12 O2 K1 -88.3(6) . . . 3_666 ?
C1 N12 O2 K1 92.3(5) . . . 3_666 ?
O3 N12 O2 K2 165.2(4) . . . 3_666 ?
C1 N12 O2 K2 -14.2(6) . . . 3_666 ?
O2 N12 O3 K2 161.4(4) . . . 4_675 ?
C1 N12 O3 K2 -19.2(7) . . . 4_675 ?
O2 N12 O3 K1 19.2(8) . . . 1_554 ?
C1 N12 O3 K1 -161.4(3) . . . 1_554 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N7 0.84(2) 2.02(2) 2.861(6) 174(7) 2_656 yes

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.131



####################################################################### 
# 
# 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_cu_20240711_zh_5818_0m
_database_code_depnum_ccdc_archive 'CCDC 2371304'
loop_
_audit_author_name
_audit_author_address
'Guofeng Zhang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 N12, H2 O, H4 N'
_chemical_formula_sum            'C4 H9 N13 O'
_chemical_formula_weight         255.24
_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 0.0181 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'

_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                   6.8574(5)
_cell_length_b                   8.0972(6)
_cell_length_c                   9.8300(7)
_cell_angle_alpha                84.665(5)
_cell_angle_beta                 72.973(6)
_cell_angle_gamma                87.546(6)
_cell_volume                     519.56(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2508
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      72.036
_cell_measurement_theta_min      4.721
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    1.123
_exptl_absorpt_correction_T_max  0.3241
_exptl_absorpt_correction_T_min  0.2106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1346 before and 0.0751 after correction.
The Ratio of minimum to maximum transmission is 0.6498.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6636
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.715
_diffrn_reflns_theta_min         4.721
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1654
_reflns_number_total             2034
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.059
_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)+(0.1027P)²+0.3366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1793
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups, All N(H,H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 N13(H13A), N13(H13B,H13C,H13D)
2.b Free rotating group:
 O1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.d X=CH2 refined with riding coordinates:
 N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N1 N 0.2487(4) 0.8515(3) 0.4422(3) 0.0450(6) Uani 1 1 d . . . . .
C1 C 0.2685(4) 0.6966(3) 0.4059(3) 0.0340(6) Uani 1 1 d . . . . .
C2 C 0.2445(4) 0.3945(3) 0.4885(3) 0.0337(6) Uani 1 1 d . . . . .
N2 N 0.2689(4) 0.9429(3) 0.3167(3) 0.0486(7) Uani 1 1 d . . . . .
N3 N 0.2982(4) 0.8438(3) 0.2147(3) 0.0465(6) Uani 1 1 d . . . . .
C3 C 0.2290(4) 0.4277(3) 0.6995(3) 0.0324(6) Uani 1 1 d . . . . .
N4 N 0.2988(4) 0.6836(3) 0.2682(3) 0.0423(6) Uani 1 1 d . . . . .
C4 C 0.2669(4) 0.4790(4) 0.9363(3) 0.0387(6) Uani 1 1 d . . . . .
H4 H 0.321106 0.586224 0.915448 0.046 Uiso 1 1 calc R U . . .
N5 N 0.2561(3) 0.5586(3) 0.5048(2) 0.0347(5) Uani 1 1 d . . . . .
N6 N 0.2439(3) 0.5809(3) 0.6451(2) 0.0361(5) Uani 1 1 d . . . . .
N7 N 0.2280(3) 0.3075(3) 0.6133(2) 0.0350(5) Uani 1 1 d . . . . .
N8 N 0.2484(4) 0.3341(3) 0.3669(2) 0.0416(6) Uani 1 1 d . . . . .
H8A H 0.239724 0.227727 0.363642 0.050 Uiso 1 1 calc R U . . .
H8B H 0.259564 0.400769 0.290471 0.050 Uiso 1 1 calc R U . . .
N9 N 0.2159(3) 0.3890(3) 0.8440(2) 0.0343(5) Uani 1 1 d . . . . .
N10 N 0.1442(4) 0.2415(3) 0.9129(3) 0.0445(6) Uani 1 1 d . . . . .
N11 N 0.1518(4) 0.2458(3) 1.0417(3) 0.0475(6) Uani 1 1 d . . . . .
N12 N 0.2284(4) 0.3922(3) 1.0601(3) 0.0436(6) Uani 1 1 d . . . . .
O1 O 0.1578(3) 0.9541(2) 0.72696(18) 0.0314(4) Uani 1 1 d G . . . .
H1A H 0.017070 0.924166 0.778253 0.047 Uiso 1 1 d G U . . .
H1B H 0.148098 1.049036 0.715167 0.047 Uiso 1 1 d G U . . .
N13 N 0.3875(3) 0.8542(3) 0.9132(2) 0.0348(5) Uani 1 1 d . . . . .
H13A H 0.273446 0.836018 0.889632 0.042 Uiso 1 1 d R U . . .
H13B H 0.355456 0.865528 1.007492 0.042 Uiso 1 1 d R U . . .
H13C H 0.501226 0.792947 0.893252 0.042 Uiso 1 1 d R U . . .
H13D H 0.411936 0.957128 0.868342 0.042 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.326(4) . ?
N1 N2 1.352(3) . ?
C1 N4 1.321(4) . ?
C1 N5 1.399(3) . ?
C2 N5 1.361(3) . ?
C2 N7 1.334(3) . ?
C2 N8 1.325(4) . ?
N2 N3 1.307(4) . ?
N3 N4 1.354(3) . ?
C3 N6 1.300(3) . ?
C3 N7 1.350(4) . ?
C3 N9 1.403(3) . ?
C4 H4 0.9400 . ?
C4 N9 1.345(4) . ?
C4 N12 1.309(4) . ?
N5 N6 1.385(3) . ?
N8 H8A 0.8700 . ?
N8 H8B 0.8700 . ?
N9 N10 1.353(3) . ?
N10 N11 1.286(3) . ?
N11 N12 1.365(4) . ?
O1 H1A 0.9783 . ?
O1 H1B 0.7696 . ?
N13 H13A 0.9002 . ?
N13 H13B 0.8999 . ?
N13 H13C 0.8876 . ?
N13 H13D 0.9041 . ?

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
C1 N1 N2 103.4(2) . . ?
N1 C1 N5 123.0(2) . . ?
N4 C1 N1 114.2(2) . . ?
N4 C1 N5 122.8(2) . . ?
N7 C2 N5 109.0(2) . . ?
N8 C2 N5 124.5(2) . . ?
N8 C2 N7 126.5(3) . . ?
N3 N2 N1 109.3(2) . . ?
N2 N3 N4 110.3(2) . . ?
N6 C3 N7 118.3(2) . . ?
N6 C3 N9 120.6(2) . . ?
N7 C3 N9 121.1(2) . . ?
C1 N4 N3 102.8(2) . . ?
N9 C4 H4 125.8 . . ?
N12 C4 H4 125.8 . . ?
N12 C4 N9 108.5(3) . . ?
C2 N5 C1 129.9(2) . . ?
C2 N5 N6 110.2(2) . . ?
N6 N5 C1 119.8(2) . . ?
C3 N6 N5 100.3(2) . . ?
C2 N7 C3 102.1(2) . . ?
C2 N8 H8A 120.0 . . ?
C2 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C4 N9 C3 130.0(2) . . ?
C4 N9 N10 108.5(2) . . ?
N10 N9 C3 121.5(2) . . ?
N11 N10 N9 105.9(2) . . ?
N10 N11 N12 111.4(2) . . ?
C4 N12 N11 105.8(2) . . ?
H1A O1 H1B 101.5 . . ?
H13A N13 H13B 109.5 . . ?
H13A N13 H13C 126.4 . . ?
H13A N13 H13D 97.2 . . ?
H13B N13 H13C 105.4 . . ?
H13B N13 H13D 106.8 . . ?
H13C N13 H13D 110.2 . . ?

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
N1 C1 N4 N3 0.2(3) . . . . ?
N1 C1 N5 C2 169.7(3) . . . . ?
N1 C1 N5 N6 -7.0(4) . . . . ?
N1 N2 N3 N4 -0.1(3) . . . . ?
C1 N1 N2 N3 0.2(3) . . . . ?
C1 N5 N6 C3 178.2(2) . . . . ?
C2 N5 N6 C3 0.9(3) . . . . ?
N2 N1 C1 N4 -0.2(3) . . . . ?
N2 N1 C1 N5 -179.5(2) . . . . ?
N2 N3 N4 C1 -0.1(3) . . . . ?
C3 N9 N10 N11 -179.9(2) . . . . ?
N4 C1 N5 C2 -9.5(4) . . . . ?
N4 C1 N5 N6 173.8(2) . . . . ?
C4 N9 N10 N11 0.5(3) . . . . ?
N5 C1 N4 N3 179.4(2) . . . . ?
N5 C2 N7 C3 0.5(3) . . . . ?
N6 C3 N7 C2 0.1(3) . . . . ?
N6 C3 N9 C4 -19.2(4) . . . . ?
N6 C3 N9 N10 161.2(2) . . . . ?
N7 C2 N5 C1 -177.9(2) . . . . ?
N7 C2 N5 N6 -0.9(3) . . . . ?
N7 C3 N6 N5 -0.6(3) . . . . ?
N7 C3 N9 C4 160.3(3) . . . . ?
N7 C3 N9 N10 -19.3(4) . . . . ?
N8 C2 N5 C1 1.8(4) . . . . ?
N8 C2 N5 N6 178.8(2) . . . . ?
N8 C2 N7 C3 -179.2(3) . . . . ?
N9 C3 N6 N5 178.9(2) . . . . ?
N9 C3 N7 C2 -179.5(2) . . . . ?
N9 C4 N12 N11 -0.1(3) . . . . ?
N9 N10 N11 N12 -0.5(3) . . . . ?
N10 N11 N12 C4 0.4(3) . . . . ?
N12 C4 N9 C3 -179.9(2) . . . . ?
N12 C4 N9 N10 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_20240803_zh_240731099543_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2376609'
loop_
_audit_author_name
_audit_author_address
'Guofeng Zhang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-08-09 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-08-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N18, 2(C2 H6 O S)'
_chemical_formula_sum            'C10 H18 N18 O2 S2'
_chemical_formula_weight         486.54
_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 0.0181 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'
S S 0.3331 0.5567 '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                   19.516(6)
_cell_length_b                   6.990(2)
_cell_length_c                   15.323(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.90(2)
_cell_angle_gamma                90
_cell_volume                     2075.2(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1902
_cell_measurement_temperature    223.15
_cell_measurement_theta_max      66.742
_cell_measurement_theta_min      5.989
_shelx_estimated_absorpt_T_max   0.729
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    2.809
_exptl_absorpt_correction_T_max  0.3241
_exptl_absorpt_correction_T_min  0.2126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1599 before and 0.0913 after correction.
The Ratio of minimum to maximum transmission is 0.6560.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14022
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.622
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_temperature      223.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2689
_reflns_number_total             4032
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0842
_refine_ls_restrained_S_all      1.063
_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)+(0.1531P)²+2.7981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2493
_refine_ls_wR_factor_ref         0.2716
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N18(H18)
2.b X=CH2 refined with riding coordinates:
 N6(H6A,H6B), N14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.2899(2) 0.0089(7) -0.0680(3) 0.0392(10) Uani 1 1 d . . . . .
O1 O 0.1160(2) -0.1936(7) -0.0993(3) 0.0630(13) Uani 1 1 d . . . . .
S1 S 0.04606(7) -0.1116(2) -0.12972(11) 0.0504(4) Uani 1 1 d . . . . .
C1 C 0.3313(2) 0.0812(8) -0.1223(4) 0.0367(11) Uani 1 1 d . . . . .
C2 C 0.4507(2) 0.2014(8) -0.1404(4) 0.0359(11) Uani 1 1 d . . . . .
N2 N 0.2355(2) -0.0339(7) -0.1249(3) 0.0413(11) Uani 1 1 d . . . . .
H2 H 0.198003 -0.083108 -0.108739 0.050 Uiso 1 1 calc R U . . .
O2 O 0.8124(2) 0.6188(6) 0.0754(3) 0.0483(10) Uani 1 1 d . . . . .
S2 S 0.78650(7) 0.4792(2) 0.00233(10) 0.0440(4) Uani 1 1 d . . . . .
N3 N 0.2421(3) 0.0030(8) -0.2065(3) 0.0476(12) Uani 1 1 d . . . . .
C3 C 0.4822(2) 0.2301(7) -0.0049(4) 0.0348(11) Uani 1 1 d . . . . .
N4 N 0.3041(2) 0.0807(8) -0.2067(3) 0.0472(12) Uani 1 1 d . . . . .
C4 C 0.6163(2) 0.3523(7) 0.1564(3) 0.0346(11) Uani 1 1 d . . . . .
C5 C 0.6450(2) 0.3561(8) 0.2937(4) 0.0357(11) Uani 1 1 d . . . . .
N5 N 0.3969(2) 0.1503(6) -0.0928(3) 0.0364(10) Uani 1 1 d . . . . .
C6 C 0.7664(3) 0.4610(8) 0.2844(4) 0.0367(11) Uani 1 1 d . . . . .
N6 N 0.4448(2) 0.1997(8) -0.2280(3) 0.0443(11) Uani 1 1 d . . . . .
H6A H 0.479337 0.235995 -0.255107 0.053 Uiso 1 1 calc R U . . .
H6B H 0.406516 0.162405 -0.258126 0.053 Uiso 1 1 calc R U . . .
N7 N 0.5047(2) 0.2535(6) -0.0850(3) 0.0356(10) Uani 1 1 d . . . . .
C7 C 0.0490(4) -0.0368(12) -0.2396(5) 0.0663(19) Uani 1 1 d . . . . .
H7A H 0.082695 0.064843 -0.240727 0.099 Uiso 1 1 calc R U . . .
H7B H 0.003869 0.009856 -0.263877 0.099 Uiso 1 1 calc R U . . .
H7C H 0.061931 -0.143987 -0.274264 0.099 Uiso 1 1 calc R U . . .
N8 N 0.4182(2) 0.1677(6) -0.0049(3) 0.0358(10) Uani 1 1 d . . . . .
C8 C 0.0444(4) 0.1167(11) -0.0795(5) 0.0642(18) Uani 1 1 d . . . . .
H8A H 0.050736 0.102165 -0.016134 0.096 Uiso 1 1 calc R U . . .
H8B H 0.000387 0.177750 -0.097624 0.096 Uiso 1 1 calc R U . . .
H8C H 0.081331 0.195084 -0.097435 0.096 Uiso 1 1 calc R U . . .
C9 C 0.7183(4) 0.6020(10) -0.0610(5) 0.0594(17) Uani 1 1 d . . . . .
H9A H 0.678672 0.608000 -0.028517 0.089 Uiso 1 1 calc R U . . .
H9B H 0.705864 0.534527 -0.115903 0.089 Uiso 1 1 calc R U . . .
H9C H 0.733153 0.730707 -0.073168 0.089 Uiso 1 1 calc R U . . .
N9 N 0.5194(2) 0.2634(6) 0.0770(3) 0.0378(10) Uani 1 1 d . . . . .
N10 N 0.5795(2) 0.3265(6) 0.0726(3) 0.0362(10) Uani 1 1 d . . . . .
C10 C 0.8504(4) 0.4972(10) -0.0706(5) 0.0595(17) Uani 1 1 d . . . . .
H10A H 0.857709 0.630723 -0.083930 0.089 Uiso 1 1 calc R U . . .
H10B H 0.835033 0.428773 -0.124510 0.089 Uiso 1 1 calc R U . . .
H10C H 0.893204 0.441806 -0.043214 0.089 Uiso 1 1 calc R U . . .
N11 N 0.6792(2) 0.4213(7) 0.1612(3) 0.0376(10) Uani 1 1 d . . . . .
N12 N 0.6986(2) 0.4241(6) 0.2513(3) 0.0356(10) Uani 1 1 d . . . . .
N13 N 0.5921(2) 0.3104(6) 0.2348(3) 0.0357(10) Uani 1 1 d . . . . .
N14 N 0.6483(2) 0.3365(8) 0.3803(3) 0.0458(12) Uani 1 1 d . . . . .
H14A H 0.613402 0.289488 0.403478 0.055 Uiso 1 1 calc R U . . .
H14B H 0.685459 0.370616 0.413929 0.055 Uiso 1 1 calc R U . . .
N15 N 0.7923(2) 0.4469(8) 0.3680(3) 0.0481(12) Uani 1 1 d . . . . .
N16 N 0.8599(3) 0.4961(8) 0.3684(4) 0.0529(13) Uani 1 1 d . . . . .
N17 N 0.8731(2) 0.5346(8) 0.2887(3) 0.0504(12) Uani 1 1 d . . . . .
N18 N 0.8142(2) 0.5157(7) 0.2351(3) 0.0433(11) Uani 1 1 d . . . . .
H18 H 0.808408 0.535540 0.178633 0.052 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
N1 C1 1.327(7) . ?
N1 N2 1.325(6) . ?
O1 S1 1.503(5) . ?
S1 C7 1.770(8) . ?
S1 C8 1.773(8) . ?
C1 N4 1.338(7) . ?
C1 N5 1.391(6) . ?
C2 N5 1.395(6) . ?
C2 N6 1.333(7) . ?
C2 N7 1.323(7) . ?
N2 H2 0.8700 . ?
N2 N3 1.299(7) . ?
O2 S2 1.525(4) . ?
S2 C9 1.771(7) . ?
S2 C10 1.775(7) . ?
N3 N4 1.326(7) . ?
C3 N7 1.361(7) . ?
C3 N8 1.322(6) . ?
C3 N9 1.392(7) . ?
C4 N10 1.406(7) . ?
C4 N11 1.312(7) . ?
C4 N13 1.375(7) . ?
C5 N12 1.380(6) . ?
C5 N13 1.327(7) . ?
C5 N14 1.328(7) . ?
N5 N8 1.367(6) . ?
C6 N12 1.384(6) . ?
C6 N15 1.322(8) . ?
C6 N18 1.326(7) . ?
N6 H6A 0.8700 . ?
N6 H6B 0.8700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
N9 N10 1.263(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
N11 N12 1.387(6) . ?
N14 H14A 0.8700 . ?
N14 H14B 0.8700 . ?
N15 N16 1.361(7) . ?
N16 N17 1.307(8) . ?
N17 N18 1.336(7) . ?
N18 H18 0.8700 . ?

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
N2 N1 C1 100.0(4) . . ?
O1 S1 C7 106.0(3) . . ?
O1 S1 C8 105.7(3) . . ?
C7 S1 C8 98.7(4) . . ?
N1 C1 N4 113.8(5) . . ?
N1 C1 N5 122.3(5) . . ?
N4 C1 N5 123.9(5) . . ?
N6 C2 N5 123.1(5) . . ?
N7 C2 N5 109.0(5) . . ?
N7 C2 N6 127.9(5) . . ?
N1 N2 H2 122.5 . . ?
N3 N2 N1 115.0(5) . . ?
N3 N2 H2 122.5 . . ?
O2 S2 C9 104.7(3) . . ?
O2 S2 C10 102.8(3) . . ?
C9 S2 C10 99.1(4) . . ?
N2 N3 N4 106.3(5) . . ?
N7 C3 N9 127.1(4) . . ?
N8 C3 N7 116.5(5) . . ?
N8 C3 N9 116.4(5) . . ?
N3 N4 C1 104.8(5) . . ?
N11 C4 N10 118.0(5) . . ?
N11 C4 N13 116.6(5) . . ?
N13 C4 N10 125.4(4) . . ?
N13 C5 N12 109.5(5) . . ?
N13 C5 N14 126.5(5) . . ?
N14 C5 N12 123.9(5) . . ?
C1 N5 C2 129.8(5) . . ?
N8 N5 C1 120.7(4) . . ?
N8 N5 C2 109.4(4) . . ?
N15 C6 N12 125.4(5) . . ?
N15 C6 N18 111.1(5) . . ?
N18 C6 N12 123.5(5) . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C2 N7 C3 103.1(4) . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 N8 N5 101.8(4) . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S2 C9 H9A 109.5 . . ?
S2 C9 H9B 109.5 . . ?
S2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N10 N9 C3 113.5(4) . . ?
N9 N10 C4 111.9(4) . . ?
S2 C10 H10A 109.5 . . ?
S2 C10 H10B 109.5 . . ?
S2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 N11 N12 101.6(4) . . ?
C5 N12 C6 129.5(5) . . ?
C5 N12 N11 109.4(4) . . ?
C6 N12 N11 120.2(4) . . ?
C5 N13 C4 102.7(4) . . ?
C5 N14 H14A 120.0 . . ?
C5 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
C6 N15 N16 104.1(5) . . ?
N17 N16 N15 110.4(5) . . ?
N16 N17 N18 107.6(4) . . ?
C6 N18 N17 106.9(5) . . ?
C6 N18 H18 126.6 . . ?
N17 N18 H18 126.6 . . ?

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
N1 C1 N4 N3 -0.3(7) . . . . ?
N1 C1 N5 C2 168.4(5) . . . . ?
N1 C1 N5 N8 -8.0(8) . . . . ?
N1 N2 N3 N4 -1.7(6) . . . . ?
C1 N1 N2 N3 1.4(6) . . . . ?
C1 N5 N8 C3 178.0(4) . . . . ?
C2 N5 N8 C3 0.9(5) . . . . ?
N2 N1 C1 N4 -0.6(6) . . . . ?
N2 N1 C1 N5 179.5(5) . . . . ?
N2 N3 N4 C1 1.1(6) . . . . ?
C3 N9 N10 C4 -178.0(4) . . . . ?
N4 C1 N5 C2 -11.5(9) . . . . ?
N4 C1 N5 N8 172.1(5) . . . . ?
C4 N11 N12 C5 -0.1(5) . . . . ?
C4 N11 N12 C6 170.1(5) . . . . ?
N5 C1 N4 N3 179.6(5) . . . . ?
N5 C2 N7 C3 0.7(5) . . . . ?
C6 N15 N16 N17 -0.8(7) . . . . ?
N6 C2 N5 C1 3.7(9) . . . . ?
N6 C2 N5 N8 -179.6(5) . . . . ?
N6 C2 N7 C3 179.1(5) . . . . ?
N7 C2 N5 C1 -177.8(5) . . . . ?
N7 C2 N5 N8 -1.1(6) . . . . ?
N7 C3 N8 N5 -0.6(6) . . . . ?
N7 C3 N9 N10 1.9(7) . . . . ?
N8 C3 N7 C2 -0.1(6) . . . . ?
N8 C3 N9 N10 -178.6(4) . . . . ?
N9 C3 N7 C2 179.4(5) . . . . ?
N9 C3 N8 N5 179.9(4) . . . . ?
N10 C4 N11 N12 -179.3(4) . . . . ?
N10 C4 N13 C5 179.2(5) . . . . ?
N11 C4 N10 N9 -178.6(5) . . . . ?
N11 C4 N13 C5 -0.5(6) . . . . ?
N12 C5 N13 C4 0.4(6) . . . . ?
N12 C6 N15 N16 179.9(5) . . . . ?
N12 C6 N18 N17 -179.0(5) . . . . ?
N13 C4 N10 N9 1.8(7) . . . . ?
N13 C4 N11 N12 0.4(6) . . . . ?
N13 C5 N12 C6 -169.2(5) . . . . ?
N13 C5 N12 N11 -0.2(6) . . . . ?
N14 C5 N12 C6 9.1(9) . . . . ?
N14 C5 N12 N11 178.2(5) . . . . ?
N14 C5 N13 C4 -177.9(5) . . . . ?
N15 C6 N12 C5 -4.1(9) . . . . ?
N15 C6 N12 N11 -172.2(5) . . . . ?
N15 C6 N18 N17 0.9(7) . . . . ?
N15 N16 N17 N18 1.4(7) . . . . ?
N16 N17 N18 C6 -1.4(7) . . . . ?
N18 C6 N12 C5 175.8(5) . . . . ?
N18 C6 N12 N11 7.7(8) . . . . ?
N18 C6 N15 N16 -0.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_20240817_ys_240809183586_1_
_database_code_depnum_ccdc_archive 'CCDC 2378852'
loop_
_audit_author_name
_audit_author_address
'Guofeng Zhang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-08-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H6 N18), 3(C2 H6 O S)'
_chemical_formula_sum            'C18 H30 N36 O3 S3'
_chemical_formula_weight         894.96
_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 0.0181 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'
S S 0.3331 0.5567 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   36.782(2)
_cell_length_b                   6.9282(5)
_cell_length_c                   15.3841(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.657(5)
_cell_angle_gamma                90
_cell_volume                     3775.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1912
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      67.103
_cell_measurement_theta_min      2.495
_shelx_estimated_absorpt_T_max   0.787
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1101 before and 0.0720 after correction.
The Ratio of minimum to maximum transmission is 0.8802.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19013
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.423
_diffrn_reflns_theta_min         2.495
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2307
_reflns_number_total             3478
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3478
_refine_ls_number_restraints     128
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.032
_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)+(0.0890P)²+0.3773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1610
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1-C9 \\sim S1A-C9A
 with sigma of 0.02
 S1-O1 \\sim S1A-O1A
 with sigma of 0.02
 S1-C8 \\sim S1A-C8A
 with sigma of 0.02
 C9-O1 \\sim C9A-O1A
 with sigma of 0.04
 C9-C8 \\sim C9A-C8A
 with sigma of 0.04
 O1-C8 \\sim O1A-C8A
 with sigma of 0.04
 S1A-C8A \\sim S1A-C9A
 with sigma of 0.02
 S1-C8 \\sim S1-C9
 with sigma of 0.02
 S2-C10 \\sim S2-C2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S1 \\sim O1 \\sim C8 \\sim C9 \\sim S1A \\sim O1A \\sim C8A \\sim C9A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
S2 \\sim O2 \\sim C2 \\sim C10: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 S2, O2, C2, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(S1A)=Sof(O1A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=
 Sof(H9AC)=Sof(H9AB)=1-FVAR(1)
 Sof(S1)=Sof(O1)=Sof(C8)=Sof(H8A)=Sof(H8C)=Sof(H8B)=Sof(C9)=Sof(H9A)=Sof(H9B)=
 Sof(H9C)=FVAR(1)
 Fixed Sof: S2(0.5) O2(0.5) C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C10(0.5)
 H10A(0.5) H10C(0.5) H10B(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N17(H17)
6.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N14(H14A,H14B)
6.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C10(H10A,H10C,H10B), C8(H8A,H8C,H8B), C9(H9A,H9B,H9C),
 C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AC,H9AB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.08355(8) 0.7526(4) 0.1987(2) 0.0656(7) Uani 1 1 d . . . . .
H1 H 0.084901 0.762591 0.255844 0.079 Uiso 1 1 calc R U . . .
N2 N 0.05274(10) 0.7836(5) 0.1305(3) 0.0839(10) Uani 1 1 d . . . . .
N3 N 0.06252(11) 0.7528(6) 0.0583(3) 0.1008(13) Uani 1 1 d . . . . .
N4 N 0.09991(10) 0.7016(6) 0.0766(2) 0.0920(11) Uani 1 1 d . . . . .
N5 N 0.17604(8) 0.5779(5) 0.09700(17) 0.0705(8) Uani 1 1 d . . . . .
H5A H 0.195443 0.532836 0.081397 0.085 Uiso 1 1 calc R U . . .
H5B H 0.155842 0.612358 0.055769 0.085 Uiso 1 1 calc R U . . .
N6 N 0.14767(7) 0.6567(4) 0.21428(16) 0.0515(6) Uani 1 1 d . . . . .
N7 N 0.15741(6) 0.6531(4) 0.30737(16) 0.0505(6) Uani 1 1 d . . . . .
N8 N 0.20594(6) 0.5477(4) 0.25330(15) 0.0480(5) Uani 1 1 d . . . . .
N9 N 0.21217(6) 0.5620(3) 0.41640(15) 0.0466(5) Uani 1 1 d . . . . .
N10 N 0.24551(6) 0.5062(3) 0.42412(15) 0.0452(5) Uani 1 1 d . . . . .
N11 N 0.30116(6) 0.4165(4) 0.52743(16) 0.0510(6) Uani 1 1 d . . . . .
N12 N 0.31224(6) 0.4015(3) 0.61977(16) 0.0476(5) Uani 1 1 d . . . . .
N13 N 0.25352(6) 0.5013(3) 0.58905(15) 0.0454(5) Uani 1 1 d . . . . .
N14 N 0.28568(7) 0.4569(4) 0.74322(16) 0.0546(6) Uani 1 1 d . . . . .
H14A H 0.266585 0.496271 0.761754 0.065 Uiso 1 1 calc R U . . .
H14B H 0.306440 0.421059 0.782166 0.065 Uiso 1 1 calc R U . . .
N15 N 0.36149(7) 0.3260(4) 0.7519(2) 0.0648(7) Uani 1 1 d . . . . .
N16 N 0.39587(8) 0.2492(5) 0.7661(3) 0.0782(9) Uani 1 1 d . . . . .
N17 N 0.40115(10) 0.2166(6) 0.6886(3) 0.0912(11) Uani 1 1 d . . . . .
H17 H 0.421950 0.168185 0.681325 0.109 Uiso 1 1 calc R U . . .
N18 N 0.37173(9) 0.2640(5) 0.6202(2) 0.0762(9) Uani 1 1 d . . . . .
C1 C 0.11138(9) 0.7048(5) 0.1647(2) 0.0592(8) Uani 1 1 d . . . . .
C3 C 0.17726(8) 0.5941(4) 0.1835(2) 0.0528(7) Uani 1 1 d . . . . .
C4 C 0.19236(7) 0.5873(4) 0.32539(18) 0.0451(6) Uani 1 1 d . . . . .
C5 C 0.26617(7) 0.4762(4) 0.51430(19) 0.0450(6) Uani 1 1 d . . . . .
C6 C 0.28314(7) 0.4515(4) 0.65592(18) 0.0447(6) Uani 1 1 d . . . . .
C7 C 0.34807(8) 0.3328(4) 0.6636(2) 0.0529(7) Uani 1 1 d . . . . .
S2 S 0.00278(16) 0.3521(3) 0.2333(4) 0.0782(13) Uani 0.5 1 d D U P A -1
O2 O -0.03520(14) 0.4416(10) 0.2001(6) 0.116(2) Uani 0.5 1 d . U P A -1
C2 C 0.0022(4) 0.265(2) 0.3406(8) 0.128(4) Uani 0.5 1 d D U P A -1
H2A H 0.012108 0.362851 0.385768 0.192 Uiso 0.5 1 calc R U P A -1
H2B H 0.017698 0.149674 0.354460 0.192 Uiso 0.5 1 calc R U P A -1
H2C H -0.023522 0.233799 0.340528 0.192 Uiso 0.5 1 calc R U P A -1
C10 C 0.0001(4) 0.1282(19) 0.1867(12) 0.145(5) Uani 0.5 1 d D U P A -1
H10A H 0.015663 0.039457 0.229728 0.217 Uiso 0.5 1 calc R U P A -1
H10C H 0.008884 0.133064 0.132721 0.217 Uiso 0.5 1 calc R U P A -1
H10B H -0.025947 0.084209 0.170966 0.217 Uiso 0.5 1 calc R U P A -1
S1 S 0.08822(4) 0.7120(2) 0.43187(10) 0.0761(5) Uani 0.772(4) 1 d D U P B 1
O1 O 0.07861(11) 0.8537(6) 0.3538(3) 0.0877(12) Uani 0.772(4) 1 d D U P B 1
C8 C 0.0505(4) 0.751(2) 0.4826(10) 0.104(3) Uani 0.772(4) 1 d D U P B 1
H8A H 0.053982 0.668468 0.535289 0.156 Uiso 0.772(4) 1 calc R U P B 1
H8C H 0.026639 0.719396 0.439460 0.156 Uiso 0.772(4) 1 calc R U P B 1
H8B H 0.050284 0.884674 0.500521 0.156 Uiso 0.772(4) 1 calc R U P B 1
C9 C 0.1245(2) 0.8322(13) 0.5128(7) 0.090(2) Uani 0.772(4) 1 d D U P B 1
H9A H 0.148119 0.819705 0.496448 0.134 Uiso 0.772(4) 1 calc R U P B 1
H9B H 0.127240 0.775095 0.571786 0.134 Uiso 0.772(4) 1 calc R U P B 1
H9C H 0.118174 0.967762 0.514581 0.134 Uiso 0.772(4) 1 calc R U P B 1
S1A S 0.07227(12) 0.8233(7) 0.4253(3) 0.0719(16) Uani 0.228(4) 1 d D U P B 2
O1A O 0.0677(3) 0.6670(17) 0.3541(7) 0.074(3) Uani 0.228(4) 1 d D U P B 2
C8A C 0.1180(6) 0.776(4) 0.498(2) 0.077(5) Uani 0.228(4) 1 d D U P B 2
H8AA H 0.118652 0.646559 0.522524 0.116 Uiso 0.228(4) 1 calc R U P B 2
H8AB H 0.123635 0.868748 0.547128 0.116 Uiso 0.228(4) 1 calc R U P B 2
H8AC H 0.136690 0.786802 0.464249 0.116 Uiso 0.228(4) 1 calc R U P B 2
C9A C 0.0463(11) 0.724(7) 0.498(3) 0.083(6) Uani 0.228(4) 1 d D U P B 2
H9AA H 0.063828 0.673861 0.552218 0.124 Uiso 0.228(4) 1 calc R U P B 2
H9AC H 0.030222 0.620669 0.466958 0.124 Uiso 0.228(4) 1 calc R U P B 2
H9AB H 0.030931 0.824231 0.514265 0.124 Uiso 0.228(4) 1 calc R U P B 2


_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
N1 H1 0.8700 . ?
N1 N2 1.338(4) . ?
N1 C1 1.311(5) . ?
N2 N3 1.274(6) . ?
N3 N4 1.374(5) . ?
N4 C1 1.307(5) . ?
N5 H5A 0.8700 . ?
N5 H5B 0.8700 . ?
N5 C3 1.324(4) . ?
N6 N7 1.380(3) . ?
N6 C1 1.387(4) . ?
N6 C3 1.369(4) . ?
N7 C4 1.321(4) . ?
N8 C3 1.326(4) . ?
N8 C4 1.362(4) . ?
N9 N10 1.260(3) . ?
N9 C4 1.404(4) . ?
N10 C5 1.406(4) . ?
N11 N12 1.372(3) . ?
N11 C5 1.315(4) . ?
N12 C6 1.377(4) . ?
N12 C7 1.392(4) . ?
N13 C5 1.363(4) . ?
N13 C6 1.326(4) . ?
N14 H14A 0.8700 . ?
N14 H14B 0.8700 . ?
N14 C6 1.321(4) . ?
N15 N16 1.335(4) . ?
N15 C7 1.316(4) . ?
N16 N17 1.279(5) . ?
N17 H17 0.8700 . ?
N17 N18 1.331(5) . ?
N18 C7 1.321(4) . ?
S2 O2 1.487(8) . ?
S2 C2 1.764(11) . ?
S2 C10 1.701(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10C 0.9700 . ?
C10 H10B 0.9700 . ?
S1 O1 1.517(4) . ?
S1 C8 1.787(10) . ?
S1 C9 1.770(7) . ?
C8 H8A 0.9700 . ?
C8 H8C 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
S1A O1A 1.516(11) . ?
S1A C8A 1.783(15) . ?
S1A C9A 1.792(16) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A H8AC 0.9700 . ?
C9A H9AA 0.9700 . ?
C9A H9AC 0.9700 . ?
C9A H9AB 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 125.8 . . ?
C1 N1 H1 125.8 . . ?
C1 N1 N2 108.4(3) . . ?
N3 N2 N1 106.2(3) . . ?
N2 N3 N4 111.5(3) . . ?
C1 N4 N3 103.5(4) . . ?
H5A N5 H5B 120.0 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
N7 N6 C1 121.1(2) . . ?
C3 N6 N7 110.2(2) . . ?
C3 N6 C1 128.5(3) . . ?
C4 N7 N6 100.9(2) . . ?
C3 N8 C4 103.0(2) . . ?
N10 N9 C4 111.2(2) . . ?
N9 N10 C5 113.1(2) . . ?
C5 N11 N12 100.8(2) . . ?
N11 N12 C6 110.7(2) . . ?
N11 N12 C7 120.3(2) . . ?
C6 N12 C7 128.9(3) . . ?
C6 N13 C5 103.0(2) . . ?
H14A N14 H14B 120.0 . . ?
C6 N14 H14A 120.0 . . ?
C6 N14 H14B 120.0 . . ?
C7 N15 N16 105.0(3) . . ?
N17 N16 N15 107.1(3) . . ?
N16 N17 H17 123.3 . . ?
N16 N17 N18 113.5(3) . . ?
N18 N17 H17 123.3 . . ?
C7 N18 N17 101.3(3) . . ?
N1 C1 N6 125.5(3) . . ?
N4 C1 N1 110.5(3) . . ?
N4 C1 N6 124.0(3) . . ?
N5 C3 N6 124.1(3) . . ?
N5 C3 N8 126.7(3) . . ?
N8 C3 N6 109.2(2) . . ?
N7 C4 N8 116.7(2) . . ?
N7 C4 N9 117.8(2) . . ?
N8 C4 N9 125.5(2) . . ?
N11 C5 N10 116.4(2) . . ?
N11 C5 N13 117.0(2) . . ?
N13 C5 N10 126.6(2) . . ?
N13 C6 N12 108.5(2) . . ?
N14 C6 N12 124.6(2) . . ?
N14 C6 N13 126.8(2) . . ?
N15 C7 N12 123.7(3) . . ?
N15 C7 N18 113.2(3) . . ?
N18 C7 N12 123.1(3) . . ?
O2 S2 C2 102.5(6) . . ?
O2 S2 C10 107.0(7) . . ?
C10 S2 C2 93.9(9) . . ?
S2 C2 H2A 109.5 . . ?
S2 C2 H2B 109.5 . . ?
S2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
S2 C10 H10A 109.5 . . ?
S2 C10 H10C 109.5 . . ?
S2 C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10C C10 H10B 109.5 . . ?
O1 S1 C8 101.9(5) . . ?
O1 S1 C9 102.9(4) . . ?
C9 S1 C8 98.7(5) . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8C 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1A S1A C8A 103.0(11) . . ?
O1A S1A C9A 101.7(16) . . ?
C8A S1A C9A 96.2(15) . . ?
S1A C8A H8AA 109.5 . . ?
S1A C8A H8AB 109.5 . . ?
S1A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
S1A C9A H9AA 109.5 . . ?
S1A C9A H9AC 109.5 . . ?
S1A C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AC C9A H9AB 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
N1 N2 N3 N4 -0.2(5) . . . . ?
N2 N1 C1 N4 -0.5(4) . . . . ?
N2 N1 C1 N6 -178.2(3) . . . . ?
N2 N3 N4 C1 -0.1(5) . . . . ?
N3 N4 C1 N1 0.3(5) . . . . ?
N3 N4 C1 N6 178.1(3) . . . . ?
N6 N7 C4 N8 -0.2(3) . . . . ?
N6 N7 C4 N9 -179.5(2) . . . . ?
N7 N6 C1 N1 0.9(5) . . . . ?
N7 N6 C1 N4 -176.5(3) . . . . ?
N7 N6 C3 N5 178.5(3) . . . . ?
N7 N6 C3 N8 0.7(3) . . . . ?
N9 N10 C5 N11 179.5(2) . . . . ?
N9 N10 C5 N13 0.1(4) . . . . ?
N10 N9 C4 N7 -177.4(2) . . . . ?
N10 N9 C4 N8 3.4(4) . . . . ?
N11 N12 C6 N13 -0.9(3) . . . . ?
N11 N12 C6 N14 -177.8(2) . . . . ?
N11 N12 C7 N15 175.6(3) . . . . ?
N11 N12 C7 N18 -5.9(4) . . . . ?
N12 N11 C5 N10 -179.5(2) . . . . ?
N12 N11 C5 N13 0.0(3) . . . . ?
N15 N16 N17 N18 -1.1(5) . . . . ?
N16 N15 C7 N12 179.0(3) . . . . ?
N16 N15 C7 N18 0.4(4) . . . . ?
N16 N17 N18 C7 1.2(4) . . . . ?
N17 N18 C7 N12 -179.6(3) . . . . ?
N17 N18 C7 N15 -0.9(4) . . . . ?
C1 N1 N2 N3 0.4(4) . . . . ?
C1 N6 N7 C4 175.3(3) . . . . ?
C1 N6 C3 N5 3.4(5) . . . . ?
C1 N6 C3 N8 -174.4(3) . . . . ?
C3 N6 N7 C4 -0.2(3) . . . . ?
C3 N6 C1 N1 175.6(3) . . . . ?
C3 N6 C1 N4 -1.9(5) . . . . ?
C3 N8 C4 N7 0.6(3) . . . . ?
C3 N8 C4 N9 179.9(2) . . . . ?
C4 N8 C3 N5 -178.5(3) . . . . ?
C4 N8 C3 N6 -0.7(3) . . . . ?
C4 N9 N10 C5 -179.1(2) . . . . ?
C5 N11 N12 C6 0.5(3) . . . . ?
C5 N11 N12 C7 177.2(2) . . . . ?
C5 N13 C6 N12 0.8(3) . . . . ?
C5 N13 C6 N14 177.6(3) . . . . ?
C6 N12 C7 N15 -8.4(5) . . . . ?
C6 N12 C7 N18 170.1(3) . . . . ?
C6 N13 C5 N10 179.0(2) . . . . ?
C6 N13 C5 N11 -0.5(3) . . . . ?
C7 N12 C6 N13 -177.2(3) . . . . ?
C7 N12 C6 N14 5.8(4) . . . . ?
C7 N15 N16 N17 0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
