# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_LYF210104_a
_database_code_depnum_ccdc_archive 'CCDC 2053784'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00674F 2021
loop_
_audit_author_name
_audit_author_address
'YiFei Liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-01-04 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 N17 Na O2, C H4 O'
_chemical_formula_sum            'C7 H14 N17 Na O3'
_chemical_formula_weight         407.34

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2417(6)
_cell_length_b                   10.6666(7)
_cell_length_c                   11.9926(9)
_cell_angle_alpha                77.757(2)
_cell_angle_beta                 85.569(2)
_cell_angle_gamma                80.379(2)
_cell_volume                     891.72(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6471
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      27.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.143
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6948
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_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            13852
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.354
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4061
_reflns_number_gt                2921
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²+0.2204P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4061
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2396(2) 0.50410(16) 0.65824(13) 0.0328(4) Uani 1 1 d . . . . .
C2 C 1.1763(2) 0.58053(15) 0.45194(13) 0.0325(4) Uani 1 1 d . . . . .
C3 C 1.4261(2) 0.30017(17) 0.73704(14) 0.0364(4) Uani 1 1 d . . . . .
C4 C 1.5950(2) 0.14259(17) 0.62410(14) 0.0379(4) Uani 1 1 d . . . . .
C5 C 1.0157(4) 0.7655(2) 0.9841(2) 0.0698(7) Uani 1 1 d . . . . .
H5A H 1.118749 0.805106 0.998534 0.105 Uiso 1 1 calc R U . . .
H5B H 0.901094 0.808616 1.013615 0.105 Uiso 1 1 calc R U . . .
H5C H 1.008642 0.772796 0.903328 0.105 Uiso 1 1 calc R U . . .
C6 C 1.4537(4) 0.2653(2) 1.16859(19) 0.0748(7) Uani 1 1 d . . . . .
H6A H 1.333324 0.239746 1.191705 0.112 Uiso 1 1 calc R U . . .
H6B H 1.528913 0.249349 1.234137 0.112 Uiso 1 1 calc R U . . .
H6C H 1.514938 0.215973 1.114199 0.112 Uiso 1 1 calc R U . . .
C7 C 0.8763(4) 0.9701(2) 0.25283(19) 0.0698(7) Uani 1 1 d . . . . .
H7A H 0.863132 1.058946 0.260457 0.105 Uiso 1 1 d R U . . .
H7B H 0.791010 0.962512 0.198046 0.105 Uiso 1 1 d R U . . .
H7C H 1.002540 0.942045 0.227450 0.105 Uiso 1 1 d R U . . .
N1 N 1.34554(19) 0.38826(13) 0.64816(11) 0.0368(3) Uani 1 1 d . . . . .
H1 H 1.366134 0.373727 0.577819 0.055 Uiso 1 1 d R U . . .
N2 N 1.1924(2) 0.55218(14) 0.75048(12) 0.0415(4) Uani 1 1 d . . . . .
N3 N 1.0812(2) 0.66922(15) 0.71380(13) 0.0481(4) Uani 1 1 d . . . . .
N4 N 1.0607(2) 0.69216(14) 0.60584(12) 0.0445(4) Uani 1 1 d . . . . .
N5 N 1.16103(19) 0.58776(13) 0.56806(11) 0.0344(3) Uani 1 1 d . . . . .
N6 N 1.0845(2) 0.66555(14) 0.37153(11) 0.0413(4) Uani 1 1 d . . . . .
N7 N 1.1427(2) 0.61836(15) 0.27630(12) 0.0424(4) Uani 1 1 d . . . . .
N8 N 1.2603(2) 0.51187(15) 0.30306(12) 0.0440(4) Uani 1 1 d . . . . .
N9 N 1.2856(2) 0.48431(14) 0.41627(12) 0.0440(4) Uani 1 1 d . . . . .
N10 N 1.4129(2) 0.30621(16) 0.84619(12) 0.0490(4) Uani 1 1 d . . . . .
N11 N 1.5213(3) 0.19465(18) 0.89918(14) 0.0643(5) Uani 1 1 d . . . . .
N12 N 1.5971(3) 0.12390(18) 0.82897(14) 0.0596(5) Uani 1 1 d . . . . .
N13 N 1.5378(2) 0.18983(14) 0.72421(12) 0.0407(3) Uani 1 1 d . . . . .
N14 N 1.6987(2) 0.03043(16) 0.62152(14) 0.0522(4) Uani 1 1 d . . . . .
N15 N 1.7091(2) 0.03611(15) 0.50872(13) 0.0478(4) Uani 1 1 d . . . . .
H15 H 1.767915 -0.024282 0.465756 0.072 Uiso 1 1 d R U . . .
N16 N 1.6194(2) 0.14179(16) 0.44896(13) 0.0508(4) Uani 1 1 d . . . . .
N17 N 1.5446(2) 0.21302(15) 0.52340(13) 0.0500(4) Uani 1 1 d . . . . .
Na1 Na 1.26316(11) 0.47954(8) 0.95086(6) 0.0527(2) Uani 1 1 d . . . . .
O1 O 1.0432(2) 0.63263(13) 1.03851(11) 0.0567(4) Uani 1 1 d . . . . .
H1A H 1.060688 0.624894 1.119419 0.085 Uiso 1 1 d R U . . .
O2 O 1.4302(2) 0.39961(14) 1.11791(10) 0.0587(4) Uani 1 1 d . . . . .
H2 H 1.382579 0.442865 1.181008 0.088 Uiso 1 1 d R U . . .
O3 O 0.8357(2) 0.89166(13) 0.35952(12) 0.0601(4) Uani 1 1 d . . . . .
H3 H 0.919166 0.811950 0.362080 0.090 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.314(2) . ?
C1 N5 1.344(2) . ?
C1 N1 1.364(2) . ?
C2 N6 1.312(2) . ?
C2 N9 1.313(2) . ?
C2 N5 1.4059(19) . ?
C3 N10 1.319(2) . ?
C3 N13 1.343(2) . ?
C3 N1 1.359(2) . ?
C4 N14 1.307(2) . ?
C4 N17 1.322(2) . ?
C4 N13 1.406(2) . ?
C5 O1 1.417(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O2 1.420(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 O3 1.412(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N1 H1 0.8867 . ?
N2 N3 1.373(2) . ?
N2 Na1 2.4301(16) . ?
N3 N4 1.281(2) . ?
N4 N5 1.3660(19) . ?
N6 N7 1.3541(19) . ?
N7 N8 1.297(2) . ?
N8 N9 1.347(2) . ?
N10 N11 1.371(2) . ?
N10 Na1 2.5048(16) . ?
N11 N12 1.280(2) . ?
N12 N13 1.366(2) . ?
N14 N15 1.338(2) . ?
N15 N16 1.300(2) . ?
N15 H15 0.9366 . ?
N16 N17 1.320(2) . ?
Na1 O2 2.3470(15) . ?
Na1 O1 2.4308(15) . ?
Na1 O1 2.6736(18) 2_767 ?
Na1 O2 2.7381(18) 2_867 ?
Na1 Na1 3.8327(16) 2_867 ?
Na1 Na1 3.8825(16) 2_767 ?
O1 H1A 0.9726 . ?
O2 H2 0.9792 . ?
O3 H3 0.9535 . ?

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 C1 N5 108.90(14) . . ?
N2 C1 N1 128.96(15) . . ?
N5 C1 N1 122.11(14) . . ?
N6 C2 N9 114.70(14) . . ?
N6 C2 N5 124.18(14) . . ?
N9 C2 N5 121.12(15) . . ?
N10 C3 N13 108.87(15) . . ?
N10 C3 N1 128.03(16) . . ?
N13 C3 N1 123.10(14) . . ?
N14 C4 N17 115.20(15) . . ?
N14 C4 N13 124.55(16) . . ?
N17 C4 N13 120.25(15) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.4 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 N1 C1 124.16(14) . . ?
C3 N1 H1 119.7 . . ?
C1 N1 H1 116.0 . . ?
C1 N2 N3 105.31(14) . . ?
C1 N2 Na1 134.38(12) . . ?
N3 N2 Na1 120.31(10) . . ?
N4 N3 N2 111.71(13) . . ?
N3 N4 N5 105.86(14) . . ?
C1 N5 N4 108.23(13) . . ?
C1 N5 C2 129.60(14) . . ?
N4 N5 C2 122.14(13) . . ?
C2 N6 N7 102.84(13) . . ?
N8 N7 N6 109.58(13) . . ?
N7 N8 N9 109.95(13) . . ?
C2 N9 N8 102.93(13) . . ?
C3 N10 N11 104.75(14) . . ?
C3 N10 Na1 132.58(12) . . ?
N11 N10 Na1 122.39(11) . . ?
N12 N11 N10 112.52(15) . . ?
N11 N12 N13 105.25(15) . . ?
C3 N13 N12 108.61(14) . . ?
C3 N13 C4 129.43(15) . . ?
N12 N13 C4 121.95(15) . . ?
C4 N14 N15 99.30(15) . . ?
N16 N15 N14 114.73(14) . . ?
N16 N15 H15 114.6 . . ?
N14 N15 H15 130.7 . . ?
N15 N16 N17 105.79(14) . . ?
N16 N17 C4 104.98(15) . . ?
O2 Na1 N2 161.38(6) . . ?
O2 Na1 O1 93.02(5) . . ?
N2 Na1 O1 101.68(5) . . ?
O2 Na1 N10 96.48(5) . . ?
N2 Na1 N10 71.70(5) . . ?
O1 Na1 N10 165.04(7) . . ?
O2 Na1 O1 110.49(6) . 2_767 ?
N2 Na1 O1 83.32(5) . 2_767 ?
O1 Na1 O1 81.07(5) . 2_767 ?
N10 Na1 O1 84.78(5) . 2_767 ?
O2 Na1 O2 82.47(5) . 2_867 ?
N2 Na1 O2 82.68(5) . 2_867 ?
O1 Na1 O2 105.28(5) . 2_867 ?
N10 Na1 O2 87.46(5) . 2_867 ?
O1 Na1 O2 165.55(5) 2_767 2_867 ?
O2 Na1 Na1 45.09(4) . 2_867 ?
N2 Na1 Na1 119.29(5) . 2_867 ?
O1 Na1 Na1 102.74(5) . 2_867 ?
N10 Na1 Na1 92.15(5) . 2_867 ?
O1 Na1 Na1 154.97(5) 2_767 2_867 ?
O2 Na1 Na1 37.38(3) 2_867 2_867 ?
O2 Na1 Na1 105.90(5) . 2_767 ?
N2 Na1 Na1 92.67(5) . 2_767 ?
O1 Na1 Na1 42.86(4) . 2_767 ?
N10 Na1 Na1 122.83(6) . 2_767 ?
O1 Na1 Na1 38.21(3) 2_767 2_767 ?
O2 Na1 Na1 146.28(5) 2_867 2_767 ?
Na1 Na1 Na1 139.64(4) 2_867 2_767 ?
C5 O1 Na1 118.97(13) . . ?
C5 O1 Na1 113.48(14) . 2_767 ?
Na1 O1 Na1 98.93(5) . 2_767 ?
C5 O1 H1A 109.5 . . ?
Na1 O1 H1A 113.6 . . ?
Na1 O1 H1A 100.3 2_767 . ?
C6 O2 Na1 120.60(14) . . ?
C6 O2 Na1 120.17(15) . 2_867 ?
Na1 O2 Na1 97.53(5) . 2_867 ?
C6 O2 H2 104.2 . . ?
Na1 O2 H2 113.7 . . ?
Na1 O2 H2 99.0 2_867 . ?
C7 O3 H3 105.2 . . ?

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
N10 C3 N1 C1 2.8(3) . . . . ?
N13 C3 N1 C1 -176.41(16) . . . . ?
N2 C1 N1 C3 -1.2(3) . . . . ?
N5 C1 N1 C3 -179.32(15) . . . . ?
N5 C1 N2 N3 -0.01(18) . . . . ?
N1 C1 N2 N3 -178.32(16) . . . . ?
N5 C1 N2 Na1 -179.10(12) . . . . ?
N1 C1 N2 Na1 2.6(3) . . . . ?
C1 N2 N3 N4 0.0(2) . . . . ?
Na1 N2 N3 N4 179.29(12) . . . . ?
N2 N3 N4 N5 -0.1(2) . . . . ?
N2 C1 N5 N4 -0.02(19) . . . . ?
N1 C1 N5 N4 178.43(14) . . . . ?
N2 C1 N5 C2 177.71(16) . . . . ?
N1 C1 N5 C2 -3.8(3) . . . . ?
N3 N4 N5 C1 0.04(19) . . . . ?
N3 N4 N5 C2 -177.89(15) . . . . ?
N6 C2 N5 C1 176.25(16) . . . . ?
N9 C2 N5 C1 -3.0(3) . . . . ?
N6 C2 N5 N4 -6.3(3) . . . . ?
N9 C2 N5 N4 174.43(15) . . . . ?
N9 C2 N6 N7 -0.3(2) . . . . ?
N5 C2 N6 N7 -179.67(15) . . . . ?
C2 N6 N7 N8 0.37(19) . . . . ?
N6 N7 N8 N9 -0.3(2) . . . . ?
N6 C2 N9 N8 0.2(2) . . . . ?
N5 C2 N9 N8 179.53(15) . . . . ?
N7 N8 N9 C2 0.07(19) . . . . ?
N13 C3 N10 N11 -0.1(2) . . . . ?
N1 C3 N10 N11 -179.34(18) . . . . ?
N13 C3 N10 Na1 173.80(13) . . . . ?
N1 C3 N10 Na1 -5.5(3) . . . . ?
C3 N10 N11 N12 0.1(2) . . . . ?
Na1 N10 N11 N12 -174.57(15) . . . . ?
N10 N11 N12 N13 -0.1(2) . . . . ?
N10 C3 N13 N12 0.0(2) . . . . ?
N1 C3 N13 N12 179.35(16) . . . . ?
N10 C3 N13 C4 -178.96(17) . . . . ?
N1 C3 N13 C4 0.4(3) . . . . ?
N11 N12 N13 C3 0.0(2) . . . . ?
N11 N12 N13 C4 179.11(18) . . . . ?
N14 C4 N13 C3 -176.99(18) . . . . ?
N17 C4 N13 C3 3.3(3) . . . . ?
N14 C4 N13 N12 4.1(3) . . . . ?
N17 C4 N13 N12 -175.57(17) . . . . ?
N17 C4 N14 N15 -0.2(2) . . . . ?
N13 C4 N14 N15 -179.90(17) . . . . ?
C4 N14 N15 N16 -0.2(2) . . . . ?
N14 N15 N16 N17 0.5(2) . . . . ?
N15 N16 N17 C4 -0.5(2) . . . . ?
N14 C4 N17 N16 0.5(2) . . . . ?
N13 C4 N17 N16 -179.81(16) . . . . ?

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
C5 H5C N3 0.96 2.71 3.578(3) 150.5 . yes
C6 H6B N16 0.96 2.67 3.563(3) 154.7 1_556 yes
C6 H6C N11 0.96 2.63 3.451(3) 143.4 . yes
N1 H1 N9 0.89 2.11 2.7931(19) 133.0 . yes
N1 H1 N17 0.89 2.15 2.7863(19) 127.7 . yes
N15 H15 O3 0.94 1.71 2.619(2) 164.2 1_645 yes
O1 H1A N7 0.97 2.00 2.9617(19) 169.5 1_556 yes
O1 H1A N8 0.97 2.68 3.543(2) 148.3 1_556 yes
O2 H2 N8 0.98 1.87 2.8445(19) 171.2 1_556 yes
O3 H3 N6 0.95 1.79 2.743(2) 176.8 . yes

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_LYF200912_a
_database_code_depnum_ccdc_archive 'CCDC 2034088'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00674F 2021
loop_
_audit_author_name
_audit_author_address
'YiFei Liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-09-27 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 K4 N34 Na2 O5'
_chemical_formula_sum            'C8 H10 K4 N34 Na2 O5'
_chemical_formula_weight         864.88

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.9928(7)
_cell_length_b                   12.1180(5)
_cell_length_c                   16.8960(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.9610(10)
_cell_angle_gamma                90
_cell_volume                     2951.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8838
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.45

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.946
_exptl_crystal_F_000             1736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.726
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6453
_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 ?
_diffrn_reflns_number            20149
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3403
_reflns_number_gt                2671
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0646P)²+6.5145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41518(17) 0.75523(19) 0.78964(14) 0.0238(5) Uani 1 1 d . . . . .
C2 C 0.31543(17) 0.8848(2) 0.68301(15) 0.0267(5) Uani 1 1 d . . . . .
C3 C 0.41903(16) 0.56687(18) 0.79367(14) 0.0218(5) Uani 1 1 d . . . . .
C4 C 0.32764(16) 0.42916(19) 0.68995(14) 0.0227(5) Uani 1 1 d . . . . .
K1 K 0.11363(4) 0.16502(5) 0.51578(4) 0.03617(18) Uani 1 1 d . . . . .
K2 K 0.33112(5) 0.15620(5) 0.80210(4) 0.0417(2) Uani 1 1 d . . . . .
N1 N 0.38469(14) 0.65919(15) 0.75276(12) 0.0245(4) Uani 1 1 d . . . . .
N2 N 0.47765(16) 0.77716(17) 0.86163(13) 0.0318(5) Uani 1 1 d . . . . .
N3 N 0.48023(18) 0.88835(19) 0.86997(14) 0.0388(6) Uani 1 1 d . . . . .
N4 N 0.42451(17) 0.93727(18) 0.80849(14) 0.0361(5) Uani 1 1 d . . . . .
N5 N 0.38264(15) 0.85528(16) 0.75573(13) 0.0265(4) Uani 1 1 d . . . . .
N6 N 0.28092(18) 0.98592(19) 0.67144(15) 0.0394(6) Uani 1 1 d . . . . .
N7 N 0.22095(18) 0.9808(2) 0.59559(15) 0.0431(6) Uani 1 1 d . . . . .
N8 N 0.22056(17) 0.8820(2) 0.56518(15) 0.0414(6) Uani 1 1 d . . . . .
N9 N 0.28145(17) 0.81722(19) 0.62013(14) 0.0377(5) Uani 1 1 d . . . . .
N10 N 0.48089(15) 0.55053(17) 0.86760(12) 0.0274(5) Uani 1 1 d . . . . .
N11 N 0.48813(15) 0.43948(17) 0.87878(13) 0.0313(5) Uani 1 1 d . . . . .
N12 N 0.43643(15) 0.38621(17) 0.81767(13) 0.0303(5) Uani 1 1 d . . . . .
N13 N 0.39233(13) 0.46412(15) 0.76215(12) 0.0232(4) Uani 1 1 d . . . . .
N14 N 0.29734(18) 0.32672(17) 0.68068(14) 0.0366(5) Uani 1 1 d . . . . .
N15 N 0.23810(18) 0.32579(19) 0.60426(15) 0.0385(6) Uani 1 1 d . . . . .
N16 N 0.23462(17) 0.4236(2) 0.57200(14) 0.0376(5) Uani 1 1 d . . . . .
N17 N 0.29191(17) 0.49295(19) 0.62559(14) 0.0383(6) Uani 1 1 d . . . . .
O1 O 0.0774(3) 0.3561(3) 0.4239(2) 0.0961(11) Uani 1 1 d . . . . .
H1A H 0.119230 0.404896 0.444561 0.144 Uiso 1 1 d R U . . .
H1B H 0.057038 0.344863 0.364963 0.144 Uiso 1 1 d R U . . .
O2 O 0.500000 0.1643(3) 0.750000 0.0707(11) Uani 1 2 d S T P . .
H2A H 0.546740 0.163387 0.792070 0.106 Uiso 0.5 1 d R U P . .
H2B H 0.501910 0.108547 0.719980 0.106 Uiso 0.5 1 d R U P . .
O3 O 0.3983(4) 0.1265(5) 0.9670(2) 0.153(2) Uani 1 1 d . . . . .
H3A H 0.452456 0.152544 0.961211 0.229 Uiso 1 1 d R U . . .
H3B H 0.387246 0.048363 0.989581 0.229 Uiso 1 1 d R U . . .
Na1 Na 0.36801(7) 0.66434(8) 0.58063(7) 0.0345(3) 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
C1 N1 1.340(3) . ?
C1 N2 1.342(3) . ?
C1 N5 1.372(3) . ?
C2 N6 1.324(3) . ?
C2 N9 1.327(4) . ?
C2 N5 1.404(3) . ?
C3 N1 1.341(3) . ?
C3 N10 1.350(3) . ?
C3 N13 1.370(3) . ?
C4 N14 1.316(3) . ?
C4 N17 1.322(3) . ?
C4 N13 1.399(3) . ?
K1 O1 2.757(3) . ?
K1 N15 2.825(2) . ?
K1 N11 2.847(2) 8_455 ?
K1 N7 2.863(2) 1_545 ?
K1 N10 3.058(2) 4_546 ?
K1 N2 3.093(2) 4_546 ?
K1 N16 3.222(3) 7_556 ?
K1 N15 3.398(3) 7_556 ?
K1 Na1 4.1207(13) 3_445 ?
K1 Na1 4.3481(11) 7_556 ?
K1 K1 4.7378(13) 7_556 ?
K1 K2 5.0370(9) . ?
K2 O3 2.714(4) . ?
K2 N14 2.857(2) . ?
K2 O2 2.9019(7) . ?
K2 N6 2.964(3) 1_545 ?
K2 N4 2.988(2) 1_545 ?
K2 N9 3.099(3) 4_546 ?
K2 N1 3.111(2) 4_546 ?
K2 N17 3.170(3) 4_546 ?
K2 N12 3.178(2) . ?
K2 Na1 4.0129(13) 4_546 ?
K2 H3A 2.8016 . ?
K2 H2A 2.7376 2_656 ?
K2 H2B 2.6931(10) 2_656 ?
N1 Na1 2.850(2) . ?
N2 N3 1.354(3) . ?
N2 Na1 2.633(3) 2_656 ?
N3 N4 1.285(3) . ?
N4 N5 1.367(3) . ?
N6 N7 1.349(4) . ?
N7 N8 1.302(4) . ?
N8 N9 1.358(3) . ?
N8 Na1 2.520(3) 7_566 ?
N9 Na1 2.457(3) . ?
N10 N11 1.359(3) . ?
N10 Na1 2.590(2) 2_656 ?
N11 N12 1.282(3) . ?
N12 N13 1.367(3) . ?
N14 N15 1.351(3) . ?
N15 N16 1.299(3) . ?
N16 N17 1.355(3) . ?
N17 Na1 2.583(3) . ?
O1 H1A 0.8632 . ?
O1 H1B 0.9678 . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8501 . ?
O2 H2A 0.8500 2_656 ?
O2 H2B 0.8501 2_656 ?
O3 H3A 0.9012 . ?
O3 H3B 1.0510 . ?

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
N1 C1 N2 131.1(2) . . ?
N1 C1 N5 122.5(2) . . ?
N2 C1 N5 106.4(2) . . ?
N6 C2 N9 113.9(2) . . ?
N6 C2 N5 121.5(2) . . ?
N9 C2 N5 124.6(2) . . ?
N1 C3 N10 131.9(2) . . ?
N1 C3 N13 121.9(2) . . ?
N10 C3 N13 106.22(19) . . ?
N14 C4 N17 113.9(2) . . ?
N14 C4 N13 121.5(2) . . ?
N17 C4 N13 124.6(2) . . ?
O1 K1 N15 73.62(9) . . ?
O1 K1 N11 86.10(9) . 8_455 ?
N15 K1 N11 158.40(7) . 8_455 ?
O1 K1 N7 156.66(10) . 1_545 ?
N15 K1 N7 94.85(8) . 1_545 ?
N11 K1 N7 101.32(7) 8_455 1_545 ?
O1 K1 N10 133.57(10) . 4_546 ?
N15 K1 N10 109.13(6) . 4_546 ?
N11 K1 N10 90.13(6) 8_455 4_546 ?
N7 K1 N10 69.07(6) 1_545 4_546 ?
O1 K1 N2 87.31(9) . 4_546 ?
N15 K1 N2 72.07(7) . 4_546 ?
N11 K1 N2 115.13(7) 8_455 4_546 ?
N7 K1 N2 108.78(6) 1_545 4_546 ?
N10 K1 N2 53.07(6) 4_546 4_546 ?
O1 K1 N16 94.33(10) . 7_556 ?
N15 K1 N16 91.49(7) . 7_556 ?
N11 K1 N16 82.53(6) 8_455 7_556 ?
N7 K1 N16 65.20(7) 1_545 7_556 ?
N10 K1 N16 131.02(6) 4_546 7_556 ?
N2 K1 N16 162.34(6) 4_546 7_556 ?
O1 K1 N15 72.33(10) . 7_556 ?
N15 K1 N15 81.25(7) . 7_556 ?
N11 K1 N15 85.63(6) 8_455 7_556 ?
N7 K1 N15 86.07(7) 1_545 7_556 ?
N10 K1 N15 153.46(6) 4_546 7_556 ?
N2 K1 N15 150.20(6) 4_546 7_556 ?
N16 K1 N15 22.43(6) 7_556 7_556 ?
O1 K1 Na1 95.69(9) . 3_445 ?
N15 K1 Na1 111.67(6) . 3_445 ?
N11 K1 Na1 77.07(5) 8_455 3_445 ?
N7 K1 Na1 107.51(6) 1_545 3_445 ?
N10 K1 Na1 38.87(4) 4_546 3_445 ?
N2 K1 Na1 39.70(5) 4_546 3_445 ?
N16 K1 Na1 156.55(5) 7_556 3_445 ?
N15 K1 Na1 159.70(5) 7_556 3_445 ?
O1 K1 Na1 125.66(8) . 7_556 ?
N15 K1 Na1 136.95(6) . 7_556 ?
N11 K1 Na1 51.90(5) 8_455 7_556 ?
N7 K1 Na1 51.35(6) 1_545 7_556 ?
N10 K1 Na1 85.02(4) 4_546 7_556 ?
N2 K1 Na1 137.68(5) 4_546 7_556 ?
N16 K1 Na1 52.87(4) 7_556 7_556 ?
N15 K1 Na1 71.78(4) 7_556 7_556 ?
Na1 K1 Na1 104.54(2) 3_445 7_556 ?
O1 K1 K1 67.31(9) . 7_556 ?
N15 K1 K1 45.14(5) . 7_556 ?
N11 K1 K1 119.98(5) 8_455 7_556 ?
N7 K1 K1 90.07(6) 1_545 7_556 ?
N10 K1 K1 146.82(4) 4_546 7_556 ?
N2 K1 K1 116.03(5) 4_546 7_556 ?
N16 K1 K1 49.65(4) 7_556 7_556 ?
N15 K1 K1 36.11(4) 7_556 7_556 ?
Na1 K1 K1 153.24(2) 3_445 7_556 ?
Na1 K1 K1 102.20(2) 7_556 7_556 ?
O1 K1 K2 122.27(8) . . ?
N15 K1 K2 49.26(5) . . ?
N11 K1 K2 151.63(5) 8_455 . ?
N7 K1 K2 53.10(6) 1_545 . ?
N10 K1 K2 70.36(4) 4_546 . ?
N2 K1 K2 69.82(4) 4_546 . ?
N16 K1 K2 94.73(4) 7_556 . ?
N15 K1 K2 102.53(4) 7_556 . ?
Na1 K1 K2 97.73(2) 3_445 . ?
Na1 K1 K2 104.44(2) 7_556 . ?
K1 K1 K2 76.495(16) 7_556 . ?
O3 K2 N14 140.85(13) . . ?
O3 K2 O2 101.98(12) . . ?
N14 K2 O2 75.81(8) . . ?
O3 K2 N6 128.25(13) . 1_545 ?
N14 K2 N6 90.58(7) . 1_545 ?
O2 K2 N6 82.05(7) . 1_545 ?
O3 K2 N4 78.89(13) . 1_545 ?
N14 K2 N4 131.06(7) . 1_545 ?
O2 K2 N4 66.53(8) . 1_545 ?
N6 K2 N4 55.20(6) 1_545 1_545 ?
O3 K2 N9 74.91(13) . 4_546 ?
N14 K2 N9 80.76(7) . 4_546 ?
O2 K2 N9 136.86(8) . 4_546 ?
N6 K2 N9 134.26(7) 1_545 4_546 ?
N4 K2 N9 148.02(7) 1_545 4_546 ?
O3 K2 N1 111.67(13) . 4_546 ?
N14 K2 N1 79.23(6) . 4_546 ?
O2 K2 N1 146.30(4) . 4_546 ?
N6 K2 N1 75.87(6) 1_545 4_546 ?
N4 K2 N1 117.37(6) 1_545 4_546 ?
N9 K2 N1 58.39(6) 4_546 4_546 ?
O3 K2 N17 67.20(12) . 4_546 ?
N14 K2 N17 136.14(7) . 4_546 ?
O2 K2 N17 141.88(8) . 4_546 ?
N6 K2 N17 78.29(7) 1_545 4_546 ?
N4 K2 N17 75.43(6) 1_545 4_546 ?
N9 K2 N17 77.70(7) 4_546 4_546 ?
N1 K2 N17 56.93(6) 4_546 4_546 ?
O3 K2 N12 89.74(12) . . ?
N14 K2 N12 53.93(6) . . ?
O2 K2 N12 62.64(8) . . ?
N6 K2 N12 133.70(7) 1_545 . ?
N4 K2 N12 123.95(7) 1_545 . ?
N9 K2 N12 74.26(6) 4_546 . ?
N1 K2 N12 117.82(5) 4_546 . ?
N17 K2 N12 147.54(6) 4_546 . ?
O3 K2 Na1 67.21(12) . 4_546 ?
N14 K2 Na1 109.13(6) . 4_546 ?
O2 K2 Na1 168.13(3) . 4_546 ?
N6 K2 Na1 108.29(6) 1_545 4_546 ?
N4 K2 Na1 114.13(5) 1_545 4_546 ?
N9 K2 Na1 37.74(5) 4_546 4_546 ?
N1 K2 Na1 44.99(4) 4_546 4_546 ?
N17 K2 Na1 40.02(4) 4_546 4_546 ?
N12 K2 Na1 110.95(5) . 4_546 ?
O3 K2 K1 161.52(12) . . ?
N14 K2 K1 49.83(5) . . ?
O2 K2 K1 95.531(18) . . ?
N6 K2 K1 48.29(5) 1_545 . ?
N4 K2 K1 103.10(5) 1_545 . ?
N9 K2 K1 96.30(5) 4_546 . ?
N1 K2 K1 50.81(4) 4_546 . ?
N17 K2 K1 95.27(4) 4_546 . ?
N12 K2 K1 103.68(4) . . ?
Na1 K2 K1 95.78(2) 4_546 . ?
O3 K2 H3A 18.7 . . ?
N14 K2 H3A 129.8 . . ?
O2 K2 H3A 84.3 . . ?
N6 K2 H3A 132.0 1_545 . ?
N4 K2 H3A 77.1 1_545 . ?
N9 K2 H3A 83.6 4_546 . ?
N1 K2 H3A 129.3 4_546 . ?
N17 K2 H3A 85.0 4_546 . ?
N12 K2 H3A 76.0 . . ?
Na1 K2 H3A 84.3 4_546 . ?
K1 K2 H3A 179.7 . . ?
O3 K2 H2A 118.83(12) . 2_656 ?
N14 K2 H2A 64.82(8) . 2_656 ?
O2 K2 H2A 17.015(4) . 2_656 ?
N6 K2 H2A 70.29(8) 1_545 2_656 ?
N4 K2 H2A 70.58(8) 1_545 2_656 ?
N9 K2 H2A 139.09(9) 4_546 2_656 ?
N1 K2 H2A 129.31(4) 4_546 2_656 ?
N17 K2 H2A 142.84(9) 4_546 2_656 ?
N12 K2 H2A 67.90(8) . 2_656 ?
Na1 K2 H2A 173.50(5) 4_546 2_656 ?
K1 K2 H2A 78.522(17) . 2_656 ?
H3A K2 H2A 101.3 . 2_656 ?
O3 K2 H2B 90.98(12) . 2_656 ?
N14 K2 H2B 92.50(8) . 2_656 ?
O2 K2 H2B 16.950(5) . 2_656 ?
N6 K2 H2B 78.64(7) 1_545 2_656 ?
N4 K2 H2B 50.98(9) 1_545 2_656 ?
N9 K2 H2B 146.01(8) 4_546 2_656 ?
N1 K2 H2B 153.05(5) 4_546 2_656 ?
N17 K2 H2B 125.53(8) 4_546 2_656 ?
N12 K2 H2B 74.93(8) . 2_656 ?
Na1 K2 H2B 156.89(4) 4_546 2_656 ?
K1 K2 H2B 104.62(2) . 2_656 ?
H3A K2 H2B 75.3 . 2_656 ?
H2A K2 H2B 29.6 2_656 2_656 ?
C1 N1 C3 116.8(2) . . ?
C1 N1 Na1 112.24(14) . . ?
C3 N1 Na1 117.23(15) . . ?
C1 N1 K2 110.03(15) . 4_556 ?
C3 N1 K2 111.36(14) . 4_556 ?
Na1 N1 K2 84.50(6) . 4_556 ?
C1 N2 N3 106.5(2) . . ?
C1 N2 Na1 123.79(16) . 2_656 ?
N3 N2 Na1 118.75(16) . 2_656 ?
C1 N2 K1 101.13(15) . 4_556 ?
N3 N2 K1 111.88(15) . 4_556 ?
Na1 N2 K1 91.68(7) 2_656 4_556 ?
N4 N3 N2 112.4(2) . . ?
N3 N4 N5 105.8(2) . . ?
N3 N4 K2 129.26(17) . 1_565 ?
N5 N4 K2 119.69(16) . 1_565 ?
N4 N5 C1 108.9(2) . . ?
N4 N5 C2 118.4(2) . . ?
C1 N5 C2 132.7(2) . . ?
C2 N6 N7 103.2(2) . . ?
C2 N6 K2 121.71(18) . 1_565 ?
N7 N6 K2 134.89(17) . 1_565 ?
N8 N7 N6 110.3(2) . . ?
N8 N7 K1 126.16(18) . 1_565 ?
N6 N7 K1 123.57(18) . 1_565 ?
N7 N8 N9 109.4(2) . . ?
N7 N8 Na1 122.32(17) . 7_566 ?
N9 N8 Na1 127.87(19) . 7_566 ?
C2 N9 N8 103.2(2) . . ?
C2 N9 Na1 124.57(18) . . ?
N8 N9 Na1 123.77(19) . . ?
C2 N9 K2 100.55(16) . 4_556 ?
N8 N9 K2 108.16(18) . 4_556 ?
Na1 N9 K2 91.74(8) . 4_556 ?
C3 N10 N11 106.39(19) . . ?
C3 N10 Na1 123.29(15) . 2_656 ?
N11 N10 Na1 116.83(15) . 2_656 ?
C3 N10 K1 101.97(15) . 4_556 ?
N11 N10 K1 113.14(15) . 4_556 ?
Na1 N10 K1 93.33(7) 2_656 4_556 ?
N12 N11 N10 112.28(19) . . ?
N12 N11 K1 123.28(15) . 8_556 ?
N10 N11 K1 124.27(15) . 8_556 ?
N11 N12 N13 106.04(19) . . ?
N11 N12 K2 133.22(15) . . ?
N13 N12 K2 114.42(14) . . ?
N12 N13 C3 109.06(18) . . ?
N12 N13 C4 118.55(19) . . ?
C3 N13 C4 132.26(19) . . ?
C4 N14 N15 103.7(2) . . ?
C4 N14 K2 127.54(17) . . ?
N15 N14 K2 128.34(16) . . ?
N16 N15 N14 109.5(2) . . ?
N16 N15 K1 117.54(17) . . ?
N14 N15 K1 132.58(17) . . ?
N16 N15 K1 71.16(16) . 7_556 ?
N14 N15 K1 101.78(17) . 7_556 ?
K1 N15 K1 98.75(7) . 7_556 ?
N15 N16 N17 109.9(2) . . ?
N15 N16 K1 86.40(17) . 7_556 ?
N17 N16 K1 96.67(16) . 7_556 ?
C4 N17 N16 103.1(2) . . ?
C4 N17 Na1 126.91(17) . . ?
N16 N17 Na1 123.54(17) . . ?
C4 N17 K2 101.24(16) . 4_556 ?
N16 N17 K2 108.40(17) . 4_556 ?
Na1 N17 K2 87.85(7) . 4_556 ?
K1 O1 H1A 109.8 . . ?
K1 O1 H1B 114.8 . . ?
H1A O1 H1B 120.0 . . ?
K2 O2 K2 176.12(14) 2_656 . ?
K2 O2 H2A 70.5 2_656 . ?
K2 O2 H2A 109.5 . . ?
K2 O2 H2B 67.5 2_656 . ?
K2 O2 H2B 109.2 . . ?
H2A O2 H2B 109.5 . . ?
K2 O2 H2A 109.472(14) 2_656 2_656 ?
K2 O2 H2A 70.474(14) . 2_656 ?
H2A O2 H2A 178.5 . 2_656 ?
H2B O2 H2A 69.3 . 2_656 ?
K2 O2 H2B 109.23(6) 2_656 2_656 ?
K2 O2 H2B 67.47(6) . 2_656 ?
H2A O2 H2B 69.3 . 2_656 ?
H2B O2 H2B 74.7 . 2_656 ?
H2A O2 H2B 109.5 2_656 2_656 ?
K2 O3 H3A 86.1 . . ?
K2 O3 H3B 116.1 . . ?
H3A O3 H3B 126.3 . . ?
N9 Na1 N8 104.94(9) . 7_566 ?
N9 Na1 N17 102.55(10) . . ?
N8 Na1 N17 87.23(8) 7_566 . ?
N9 Na1 N10 141.99(8) . 2_656 ?
N8 Na1 N10 112.85(8) 7_566 2_656 ?
N17 Na1 N10 83.60(8) . 2_656 ?
N9 Na1 N2 89.08(8) . 2_656 ?
N8 Na1 N2 130.63(9) 7_566 2_656 ?
N17 Na1 N2 136.30(8) . 2_656 ?
N10 Na1 N2 63.48(7) 2_656 2_656 ?
N9 Na1 N1 69.15(7) . . ?
N8 Na1 N1 150.17(8) 7_566 . ?
N17 Na1 N1 66.68(7) . . ?
N10 Na1 N1 79.67(7) 2_656 . ?
N2 Na1 N1 79.15(7) 2_656 . ?
N9 Na1 K2 50.52(6) . 4_556 ?
N8 Na1 K2 102.34(7) 7_566 4_556 ?
N17 Na1 K2 52.13(6) . 4_556 ?
N10 Na1 K2 121.37(6) 2_656 4_556 ?
N2 Na1 K2 121.82(6) 2_656 4_556 ?
N1 Na1 K2 50.51(5) . 4_556 ?
N9 Na1 K1 130.39(7) . 3 ?
N8 Na1 K1 90.56(7) 7_566 3 ?
N17 Na1 K1 125.40(7) . 3 ?
N10 Na1 K1 47.81(5) 2_656 3 ?
N2 Na1 K1 48.62(5) 2_656 3 ?
N1 Na1 K1 115.93(5) . 3 ?
K2 Na1 K1 166.40(3) 4_556 3 ?
N9 Na1 K1 152.42(7) . 7_556 ?
N8 Na1 K1 59.98(6) 7_566 7_556 ?
N17 Na1 K1 56.67(6) . 7_556 ?
N10 Na1 K1 59.88(5) 2_656 7_556 ?
N2 Na1 K1 118.40(6) 2_656 7_556 ?
N1 Na1 K1 111.43(5) . 7_556 ?
K2 Na1 K1 107.14(3) 4_556 7_556 ?
K1 Na1 K1 75.46(2) 3 7_556 ?

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 N16 0.86 2.37 3.040(4) 134.4 . yes
O1 H1B O2 0.97 1.90 2.858(4) 170.9 7_556 yes
O2 H2A O1 0.85 2.16 2.858(4) 139.2 8_556 yes
O2 H2B N4 0.85 2.46 3.231(4) 151.4 2_646 yes
O2 H2B O1 0.85 2.43 2.858(4) 111.6 7_556 yes
O3 H3B N16 1.05 2.38 3.120(6) 126.4 4_546 yes

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_LYF201221_1_a
_database_code_depnum_ccdc_archive 'CCDC 2051823'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00674F 2021
loop_
_audit_author_name
_audit_author_address
'YiFei Liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 N17, H3 N O, 3(H4 N O), 2(H2 O)'
_chemical_formula_sum            'C4 H19 N21 O6'
_chemical_formula_weight         457.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3804(3)
_cell_length_b                   11.4595(5)
_cell_length_c                   11.8445(5)
_cell_angle_alpha                64.0290(10)
_cell_angle_beta                 81.549(2)
_cell_angle_gamma                89.9050(10)
_cell_volume                     888.60(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6373
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7093
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_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            12135
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.938
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4023
_reflns_number_gt                3230
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.2487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4023
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.87936(19) 0.42996(13) 0.81583(13) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.99121(19) 0.65226(13) 0.78729(13) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.62965(19) 0.37031(14) 0.75552(13) 0.0183(3) Uani 1 1 d . . . . .
C4 C 0.39655(19) 0.50897(14) 0.62593(13) 0.0182(3) Uani 1 1 d . . . . .
N1 N 0.73623(16) 0.46607(11) 0.75378(11) 0.0195(3) Uani 1 1 d . . . . .
N2 N 0.94821(18) 0.31380(12) 0.87291(13) 0.0255(3) Uani 1 1 d . . . . .
N3 N 1.09876(18) 0.33381(12) 0.91817(13) 0.0270(3) Uani 1 1 d . . . . .
N4 N 1.12812(17) 0.45306(12) 0.89384(12) 0.0246(3) Uani 1 1 d . . . . .
N5 N 0.99083(16) 0.51729(11) 0.82949(11) 0.0186(3) Uani 1 1 d . . . . .
N6 N 1.13336(18) 0.72006(13) 0.79050(14) 0.0273(3) Uani 1 1 d . . . . .
N7 N 1.08236(18) 0.84333(13) 0.74314(14) 0.0301(3) Uani 1 1 d . . . . .
N8 N 0.91797(18) 0.84522(12) 0.71417(13) 0.0278(3) Uani 1 1 d . . . . .
N9 N 0.85467(17) 0.72372(12) 0.74098(13) 0.0244(3) Uani 1 1 d . . . . .
N10 N 0.63705(19) 0.24069(12) 0.81253(13) 0.0266(3) Uani 1 1 d . . . . .
N11 N 0.4953(2) 0.19100(13) 0.78145(14) 0.0307(3) Uani 1 1 d . . . . .
N12 N 0.40143(18) 0.27929(12) 0.71127(13) 0.0258(3) Uani 1 1 d . . . . .
N13 N 0.48113(16) 0.39489(11) 0.69336(11) 0.0187(3) Uani 1 1 d . . . . .
N14 N 0.24351(18) 0.50383(13) 0.58126(13) 0.0275(3) Uani 1 1 d . . . . .
N15 N 0.20528(18) 0.62906(14) 0.52470(13) 0.0295(3) Uani 1 1 d . . . . .
N16 N 0.32994(19) 0.70238(13) 0.53616(13) 0.0286(3) Uani 1 1 d . . . . .
N17 N 0.45610(18) 0.62764(12) 0.60155(13) 0.0255(3) Uani 1 1 d . . . . .
N18 N 0.30064(19) 0.92220(13) 0.91043(13) 0.0287(3) Uani 1 1 d . . . . .
H18A H 0.263959 0.868513 0.992247 0.043 Uiso 1 1 calc R U . . .
H18B H 0.213450 0.922051 0.865957 0.043 Uiso 1 1 calc R U . . .
H18C H 0.321996 1.002357 0.901746 0.043 Uiso 1 1 calc R U . . .
N19 N 0.47807(17) 0.62164(12) 0.85430(12) 0.0234(3) Uani 1 1 d . . . . .
H19A H 0.380681 0.658266 0.820160 0.035 Uiso 1 1 calc R U . . .
H19B H 0.469148 0.536959 0.875244 0.035 Uiso 1 1 calc R U . . .
H19C H 0.579708 0.658583 0.798154 0.035 Uiso 1 1 calc R U . . .
N20 N 0.15496(18) 0.28658(12) 0.51886(13) 0.0261(3) Uani 1 1 d . . . . .
H20A H 0.047188 0.321357 0.508029 0.039 Uiso 1 1 calc R U . . .
H20B H 0.231223 0.320375 0.444947 0.039 Uiso 1 1 calc R U . . .
H20C H 0.202248 0.303752 0.575328 0.039 Uiso 1 1 calc R U . . .
N21 N 0.68554(19) 1.02119(14) 0.56211(13) 0.0311(3) Uani 1 1 d . . . . .
H21A H 0.682067 1.104730 0.545445 0.047 Uiso 1 1 calc R U . . .
H21B H 0.711845 1.014573 0.489446 0.047 Uiso 1 1 calc R U . . .
H21C H 0.771462 0.985702 0.609996 0.047 Uiso 1 1 calc R U . . .
O1 O 0.46187(15) 0.88081(10) 0.86539(10) 0.0269(3) Uani 1 1 d . . . . .
O2 O 0.48545(18) 0.63923(11) 0.96417(10) 0.0338(3) Uani 1 1 d . . . . .
H2 H 0.477211 0.729972 0.933384 0.051 Uiso 1 1 d R U . . .
O3 O 0.1301(2) 0.15145(11) 0.56339(12) 0.0447(4) Uani 1 1 d . . . . .
H3 H 0.096965 0.117054 0.640721 0.067 Uiso 1 1 calc R U . . .
O4 O 0.51434(18) 0.95595(15) 0.62733(12) 0.0474(4) Uani 1 1 d . . . . .
H4 H 0.506206 0.934410 0.715975 0.071 Uiso 1 1 d R U . . .
O5 O 0.75902(16) 0.91868(11) 0.95662(11) 0.0332(3) Uani 1 1 d . . . . .
H5A H 0.801942 0.837123 0.982856 0.050 Uiso 1 1 d R U . . .
H5B H 0.658843 0.900822 0.936056 0.050 Uiso 1 1 d R U . . .
O6 O 1.01739(18) 0.10081(12) 0.79825(12) 0.0387(3) Uani 1 1 d . . . . .
H6A H 0.923656 0.040065 0.846105 0.058 Uiso 1 1 d R U . . .
H6B H 0.993556 0.179465 0.805005 0.058 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3371(19) . ?
C1 N2 1.3408(19) . ?
C1 N5 1.3740(18) . ?
C2 N6 1.3215(19) . ?
C2 N9 1.3241(19) . ?
C2 N5 1.4016(18) . ?
C3 N10 1.3407(19) . ?
C3 N1 1.3422(18) . ?
C3 N13 1.3702(18) . ?
C4 N17 1.3216(19) . ?
C4 N14 1.3275(19) . ?
C4 N13 1.4022(19) . ?
N2 N3 1.3632(18) . ?
N3 N4 1.2787(19) . ?
N4 N5 1.3721(17) . ?
N6 N7 1.3484(18) . ?
N7 N8 1.3062(19) . ?
N8 N9 1.3525(18) . ?
N10 N11 1.3614(19) . ?
N11 N12 1.2745(19) . ?
N12 N13 1.3659(17) . ?
N14 N15 1.3417(19) . ?
N15 N16 1.308(2) . ?
N16 N17 1.3523(18) . ?
N18 O1 1.3996(17) . ?
N18 H18A 0.8900 . ?
N18 H18B 0.8900 . ?
N18 H18C 0.8900 . ?
N19 O2 1.4098(16) . ?
N19 H19A 0.8900 . ?
N19 H19B 0.8900 . ?
N19 H19C 0.8900 . ?
N20 O3 1.4024(17) . ?
N20 H20A 0.8900 . ?
N20 H20B 0.8900 . ?
N20 H20C 0.8900 . ?
N21 O4 1.4009(19) . ?
N21 H21A 0.8900 . ?
N21 H21B 0.8900 . ?
N21 H21C 0.8900 . ?
O2 H2 0.9446 . ?
O3 H3 0.8200 . ?
O4 H4 0.9600 . ?
O5 H5A 0.9186 . ?
O5 H5B 0.8631 . ?
O6 H6A 0.9084 . ?
O6 H6B 0.9530 . ?

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
N1 C1 N2 131.62(13) . . ?
N1 C1 N5 122.31(12) . . ?
N2 C1 N5 106.07(12) . . ?
N6 C2 N9 113.76(13) . . ?
N6 C2 N5 121.47(13) . . ?
N9 C2 N5 124.77(13) . . ?
N10 C3 N1 131.27(13) . . ?
N10 C3 N13 106.61(12) . . ?
N1 C3 N13 122.11(12) . . ?
N17 C4 N14 114.24(13) . . ?
N17 C4 N13 125.18(13) . . ?
N14 C4 N13 120.58(13) . . ?
C1 N1 C3 116.54(12) . . ?
C1 N2 N3 106.70(12) . . ?
N4 N3 N2 112.39(12) . . ?
N3 N4 N5 105.66(12) . . ?
N4 N5 C1 109.17(11) . . ?
N4 N5 C2 118.27(11) . . ?
C1 N5 C2 132.51(12) . . ?
C2 N6 N7 103.88(12) . . ?
N8 N7 N6 109.17(12) . . ?
N7 N8 N9 110.19(12) . . ?
C2 N9 N8 103.01(12) . . ?
C3 N10 N11 106.12(12) . . ?
N12 N11 N10 112.47(12) . . ?
N11 N12 N13 106.08(12) . . ?
N12 N13 C3 108.71(11) . . ?
N12 N13 C4 118.02(12) . . ?
C3 N13 C4 133.15(12) . . ?
C4 N14 N15 103.10(13) . . ?
N16 N15 N14 109.99(13) . . ?
N15 N16 N17 109.82(12) . . ?
C4 N17 N16 102.85(12) . . ?
O1 N18 H18A 109.5 . . ?
O1 N18 H18B 109.5 . . ?
H18A N18 H18B 109.5 . . ?
O1 N18 H18C 109.5 . . ?
H18A N18 H18C 109.5 . . ?
H18B N18 H18C 109.5 . . ?
O2 N19 H19A 109.5 . . ?
O2 N19 H19B 109.5 . . ?
H19A N19 H19B 109.5 . . ?
O2 N19 H19C 109.5 . . ?
H19A N19 H19C 109.5 . . ?
H19B N19 H19C 109.5 . . ?
O3 N20 H20A 109.5 . . ?
O3 N20 H20B 109.5 . . ?
H20A N20 H20B 109.5 . . ?
O3 N20 H20C 109.5 . . ?
H20A N20 H20C 109.5 . . ?
H20B N20 H20C 109.5 . . ?
O4 N21 H21A 109.5 . . ?
O4 N21 H21B 109.5 . . ?
H21A N21 H21B 109.5 . . ?
O4 N21 H21C 109.5 . . ?
H21A N21 H21C 109.5 . . ?
H21B N21 H21C 109.5 . . ?
N19 O2 H2 102.0 . . ?
N20 O3 H3 109.5 . . ?
N21 O4 H4 109.2 . . ?
H5A O5 H5B 96.6 . . ?
H6A O6 H6B 109.2 . . ?

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
N2 C1 N1 C3 6.3(2) . . . . ?
N5 C1 N1 C3 -174.97(12) . . . . ?
N10 C3 N1 C1 2.1(2) . . . . ?
N13 C3 N1 C1 -178.65(12) . . . . ?
N1 C1 N2 N3 178.35(15) . . . . ?
N5 C1 N2 N3 -0.50(15) . . . . ?
C1 N2 N3 N4 0.15(17) . . . . ?
N2 N3 N4 N5 0.27(17) . . . . ?
N3 N4 N5 C1 -0.58(16) . . . . ?
N3 N4 N5 C2 -178.36(12) . . . . ?
N1 C1 N5 N4 -178.31(13) . . . . ?
N2 C1 N5 N4 0.67(15) . . . . ?
N1 C1 N5 C2 -1.0(2) . . . . ?
N2 C1 N5 C2 178.02(14) . . . . ?
N6 C2 N5 N4 10.60(19) . . . . ?
N9 C2 N5 N4 -169.65(13) . . . . ?
N6 C2 N5 C1 -166.56(15) . . . . ?
N9 C2 N5 C1 13.2(2) . . . . ?
N9 C2 N6 N7 0.24(17) . . . . ?
N5 C2 N6 N7 -179.99(13) . . . . ?
C2 N6 N7 N8 -0.06(17) . . . . ?
N6 N7 N8 N9 -0.12(18) . . . . ?
N6 C2 N9 N8 -0.31(17) . . . . ?
N5 C2 N9 N8 179.93(13) . . . . ?
N7 N8 N9 C2 0.25(16) . . . . ?
N1 C3 N10 N11 -179.65(15) . . . . ?
N13 C3 N10 N11 1.03(16) . . . . ?
C3 N10 N11 N12 -0.53(18) . . . . ?
N10 N11 N12 N13 -0.21(17) . . . . ?
N11 N12 N13 C3 0.87(16) . . . . ?
N11 N12 N13 C4 -175.66(13) . . . . ?
N10 C3 N13 N12 -1.19(15) . . . . ?
N1 C3 N13 N12 179.41(12) . . . . ?
N10 C3 N13 C4 174.61(14) . . . . ?
N1 C3 N13 C4 -4.8(2) . . . . ?
N17 C4 N13 N12 179.58(13) . . . . ?
N14 C4 N13 N12 0.05(19) . . . . ?
N17 C4 N13 C3 4.1(2) . . . . ?
N14 C4 N13 C3 -175.44(14) . . . . ?
N17 C4 N14 N15 0.05(17) . . . . ?
N13 C4 N14 N15 179.63(12) . . . . ?
C4 N14 N15 N16 0.05(16) . . . . ?
N14 N15 N16 N17 -0.14(17) . . . . ?
N14 C4 N17 N16 -0.13(16) . . . . ?
N13 C4 N17 N16 -179.69(13) . . . . ?
N15 N16 N17 C4 0.16(16) . . . . ?

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
N18 H18A N2 0.89 2.39 3.1346(19) 141.1 2_667 yes
N18 H18A N10 0.89 2.33 3.0886(19) 143.8 2_667 yes
N18 H18B N7 0.89 2.33 3.138(2) 150.9 1_455 yes
N18 H18B O6 0.89 2.41 2.9573(18) 119.7 1_465 yes
N18 H18C N11 0.89 2.26 3.0222(19) 143.3 1_565 yes
N18 H18C O5 0.89 2.24 2.8822(17) 128.6 2_677 yes
N19 H19A N6 0.89 1.98 2.8504(18) 165.3 1_455 yes
N19 H19B N1 0.89 2.61 3.0671(17) 113.0 . yes
N19 H19B N4 0.89 2.64 3.0807(18) 111.6 1_455 yes
N19 H19B O2 0.89 2.15 2.8583(17) 135.9 2_667 yes
N19 H19C N9 0.89 2.07 2.9042(18) 155.3 . yes
N20 H20A N15 0.89 1.99 2.8683(19) 168.7 2_566 yes
N20 H20B N1 0.89 2.53 3.2149(18) 134.8 2_666 yes
N20 H20B N9 0.89 2.63 3.1422(19) 117.9 2_666 yes
N20 H20B N17 0.89 2.31 2.9696(19) 131.1 2_666 yes
N20 H20C N12 0.89 2.27 3.0921(19) 154.5 . yes
N20 H20C N14 0.89 2.35 2.9884(19) 129.1 . yes
N21 H21A N16 0.89 2.00 2.8655(19) 165.5 2_676 yes
N21 H21B O3 0.89 2.49 3.1539(19) 132.0 2_666 yes
N21 H21B O4 0.89 2.25 2.7813(19) 117.7 2_676 yes
N21 H21C N8 0.89 1.98 2.8229(19) 156.9 . yes
O2 H2 N18 0.94 2.49 3.3487(17) 151.4 . yes
O2 H2 O1 0.94 1.57 2.5069(15) 172.6 . yes
O3 H3 O6 0.82 1.80 2.5835(18) 159.7 1_455 yes
O4 H4 N18 0.96 2.51 3.3456(19) 145.0 . yes
O4 H4 O1 0.96 1.58 2.5290(16) 169.3 . yes
O5 H5A N3 0.92 2.00 2.8917(17) 164.4 2_767 yes
O5 H5B O1 0.86 1.84 2.6974(16) 170.7 . yes
O6 H6A O5 0.91 1.75 2.6540(17) 171.9 1_545 yes
O6 H6B N2 0.95 2.03 2.9586(17) 163.4 . yes

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_LYF210420_a
_database_code_depnum_ccdc_archive 'CCDC 2079019'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00674F 2021
loop_
_audit_author_name
_audit_author_address
'YiFei Liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-04-21 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 N17, 3(C H6 N3)'
_chemical_formula_sum            'C7 H18 N26'
_chemical_formula_weight         466.47

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2340(13)
_cell_length_b                   10.5985(19)
_cell_length_c                   13.966(3)
_cell_angle_alpha                70.681(5)
_cell_angle_beta                 89.167(6)
_cell_angle_gamma                71.541(5)
_cell_volume                     953.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8539
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.71

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6921
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_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            14916
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.157
_diffrn_reflns_theta_max         27.948
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4501
_reflns_number_gt                3621
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.2487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4501
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.83108(18) 0.31029(13) 0.14228(9) 0.0267(3) Uani 1 1 d . . . . .
C2 C 0.70553(18) 0.55718(13) 0.00742(9) 0.0256(3) Uani 1 1 d . . . . .
C3 C 0.77835(19) 0.23599(13) 0.30906(9) 0.0273(3) Uani 1 1 d . . . . .
C4 C 0.75735(19) 0.35833(13) 0.44061(9) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.77621(16) 0.34337(11) 0.22504(8) 0.0295(2) Uani 1 1 d . . . . .
N2 N 0.93105(17) 0.18517(12) 0.13211(8) 0.0346(3) Uani 1 1 d . . . . .
N3 N 0.95998(19) 0.21301(12) 0.03206(9) 0.0390(3) Uani 1 1 d . . . . .
N4 N 0.88533(18) 0.34491(12) -0.02085(8) 0.0353(3) Uani 1 1 d . . . . .
N5 N 0.80091(16) 0.40987(11) 0.04623(7) 0.0272(2) Uani 1 1 d . . . . .
N6 N 0.7173(2) 0.63157(13) -0.08786(9) 0.0436(3) Uani 1 1 d . . . . .
N7 N 0.6101(2) 0.76521(13) -0.09668(10) 0.0459(3) Uani 1 1 d . . . . .
N8 N 0.5408(2) 0.76662(12) -0.01055(9) 0.0416(3) Uani 1 1 d . . . . .
N9 N 0.59902(19) 0.63365(12) 0.05855(9) 0.0382(3) Uani 1 1 d . . . . .
N10 N 0.78648(19) 0.10249(12) 0.32214(9) 0.0380(3) Uani 1 1 d . . . . .
N11 N 0.7719(2) 0.04095(13) 0.42229(9) 0.0453(3) Uani 1 1 d . . . . .
N12 N 0.7570(2) 0.12380(12) 0.47340(9) 0.0402(3) Uani 1 1 d . . . . .
N13 N 0.76227(17) 0.24853(11) 0.40429(8) 0.0295(2) Uani 1 1 d . . . . .
N14 N 0.7505(2) 0.34015(13) 0.53898(9) 0.0409(3) Uani 1 1 d . . . . .
N15 N 0.7485(2) 0.46548(14) 0.54389(10) 0.0449(3) Uani 1 1 d . . . . .
N16 N 0.7554(2) 0.55017(13) 0.45300(9) 0.0423(3) Uani 1 1 d . . . . .
N17 N 0.76258(19) 0.48431(12) 0.38437(9) 0.0369(3) Uani 1 1 d . . . . .
C5 C 0.31486(19) 0.84273(14) 0.20561(10) 0.0296(3) Uani 1 1 d . . . . .
N18 N 0.39667(18) 0.70378(12) 0.23233(9) 0.0387(3) Uani 1 1 d . . . . .
H18A H 0.456387 0.667355 0.189175 0.046 Uiso 1 1 calc R U . . .
H18B H 0.390142 0.649855 0.292846 0.046 Uiso 1 1 calc R U . . .
N19 N 0.32496(19) 0.92534(13) 0.11275(9) 0.0422(3) Uani 1 1 d . . . . .
H19A H 0.384709 0.888829 0.069649 0.051 Uiso 1 1 calc R U . . .
H19B H 0.271801 1.015700 0.095324 0.051 Uiso 1 1 calc R U . . .
N20 N 0.22239(18) 0.89945(13) 0.27210(9) 0.0381(3) Uani 1 1 d . . . . .
H20A H 0.169314 0.989834 0.254537 0.046 Uiso 1 1 calc R U . . .
H20B H 0.215664 0.845755 0.332666 0.046 Uiso 1 1 calc R U . . .
C6 C 0.8325(2) 0.80667(14) 0.20923(10) 0.0314(3) Uani 1 1 d . . . . .
N21 N 0.88290(19) 0.67628(13) 0.20786(9) 0.0391(3) Uani 1 1 d . . . . .
H21A H 0.932160 0.657724 0.155679 0.047 Uiso 1 1 calc R U . . .
H21B H 0.866490 0.609848 0.259147 0.047 Uiso 1 1 calc R U . . .
N22 N 0.8574(2) 0.90912(13) 0.13062(9) 0.0414(3) Uani 1 1 d . . . . .
H22A H 0.906613 0.890937 0.078314 0.050 Uiso 1 1 calc R U . . .
H22B H 0.824378 0.993987 0.131756 0.050 Uiso 1 1 calc R U . . .
N23 N 0.7552(2) 0.83595(15) 0.28900(10) 0.0471(3) Uani 1 1 d . . . . .
H23A H 0.737709 0.769891 0.340187 0.057 Uiso 1 1 calc R U . . .
H23B H 0.722516 0.921031 0.289664 0.057 Uiso 1 1 calc R U . . .
C7 C 0.7321(2) 0.74320(14) 0.64413(10) 0.0325(3) Uani 1 1 d . . . . .
N24 N 0.7621(2) 0.76384(14) 0.54769(9) 0.0479(3) Uani 1 1 d . . . . .
H24A H 0.779386 0.696057 0.524049 0.058 Uiso 1 1 calc R U . . .
H24B H 0.764521 0.845092 0.508376 0.058 Uiso 1 1 calc R U . . .
N25 N 0.7284(2) 0.61911(13) 0.70439(9) 0.0443(3) Uani 1 1 d . . . . .
H25A H 0.745596 0.551204 0.680886 0.053 Uiso 1 1 calc R U . . .
H25B H 0.708746 0.605833 0.767320 0.053 Uiso 1 1 calc R U . . .
N26 N 0.7073(2) 0.84857(13) 0.67982(10) 0.0449(3) Uani 1 1 d . . . . .
H26A H 0.688685 0.835852 0.742803 0.054 Uiso 1 1 calc R U . . .
H26B H 0.709929 0.929459 0.639939 0.054 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
C1 N1 1.3354(15) . ?
C1 N2 1.3476(16) . ?
C1 N5 1.3735(16) . ?
C2 N9 1.3160(16) . ?
C2 N6 1.3208(17) . ?
C2 N5 1.4058(16) . ?
C3 N1 1.3334(16) . ?
C3 N10 1.3474(17) . ?
C3 N13 1.3794(16) . ?
C4 N17 1.3185(17) . ?
C4 N14 1.3250(16) . ?
C4 N13 1.4060(16) . ?
N2 N3 1.3569(16) . ?
N3 N4 1.2814(16) . ?
N4 N5 1.3669(14) . ?
N6 N7 1.3470(17) . ?
N7 N8 1.2992(17) . ?
N8 N9 1.3531(16) . ?
N10 N11 1.3522(17) . ?
N11 N12 1.2824(17) . ?
N12 N13 1.3666(15) . ?
N14 N15 1.3481(17) . ?
N15 N16 1.3008(18) . ?
N16 N17 1.3517(16) . ?
C5 N19 1.3192(17) . ?
C5 N18 1.3225(17) . ?
C5 N20 1.3295(16) . ?
N18 H18A 0.8600 . ?
N18 H18B 0.8600 . ?
N19 H19A 0.8600 . ?
N19 H19B 0.8600 . ?
N20 H20A 0.8600 . ?
N20 H20B 0.8600 . ?
C6 N21 1.3196(18) . ?
C6 N22 1.3215(17) . ?
C6 N23 1.3232(17) . ?
N21 H21A 0.8600 . ?
N21 H21B 0.8600 . ?
N22 H22A 0.8600 . ?
N22 H22B 0.8600 . ?
N23 H23A 0.8600 . ?
N23 H23B 0.8600 . ?
C7 N25 1.3145(18) . ?
C7 N24 1.3175(18) . ?
C7 N26 1.3292(17) . ?
N24 H24A 0.8600 . ?
N24 H24B 0.8600 . ?
N25 H25A 0.8600 . ?
N25 H25B 0.8600 . ?
N26 H26A 0.8600 . ?
N26 H26B 0.8600 . ?

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
N1 C1 N2 130.96(12) . . ?
N1 C1 N5 122.99(11) . . ?
N2 C1 N5 105.94(10) . . ?
N9 C2 N6 113.82(12) . . ?
N9 C2 N5 125.50(11) . . ?
N6 C2 N5 120.68(11) . . ?
N1 C3 N10 131.08(11) . . ?
N1 C3 N13 122.90(11) . . ?
N10 C3 N13 105.96(11) . . ?
N17 C4 N14 113.73(12) . . ?
N17 C4 N13 125.45(11) . . ?
N14 C4 N13 120.80(12) . . ?
C3 N1 C1 116.34(11) . . ?
C1 N2 N3 106.59(11) . . ?
N4 N3 N2 112.47(10) . . ?
N3 N4 N5 105.77(10) . . ?
N4 N5 C1 109.21(10) . . ?
N4 N5 C2 117.66(10) . . ?
C1 N5 C2 133.13(10) . . ?
C2 N6 N7 103.60(11) . . ?
N8 N7 N6 109.48(11) . . ?
N7 N8 N9 109.91(11) . . ?
C2 N9 N8 103.18(11) . . ?
C3 N10 N11 106.38(11) . . ?
N12 N11 N10 113.06(11) . . ?
N11 N12 N13 105.45(11) . . ?
N12 N13 C3 109.13(10) . . ?
N12 N13 C4 117.86(10) . . ?
C3 N13 C4 132.97(11) . . ?
C4 N14 N15 103.54(11) . . ?
N16 N15 N14 109.46(11) . . ?
N15 N16 N17 110.06(12) . . ?
C4 N17 N16 103.20(11) . . ?
N19 C5 N18 119.94(12) . . ?
N19 C5 N20 119.88(12) . . ?
N18 C5 N20 120.18(12) . . ?
C5 N18 H18A 120.0 . . ?
C5 N18 H18B 120.0 . . ?
H18A N18 H18B 120.0 . . ?
C5 N19 H19A 120.0 . . ?
C5 N19 H19B 120.0 . . ?
H19A N19 H19B 120.0 . . ?
C5 N20 H20A 120.0 . . ?
C5 N20 H20B 120.0 . . ?
H20A N20 H20B 120.0 . . ?
N21 C6 N22 120.24(12) . . ?
N21 C6 N23 120.22(13) . . ?
N22 C6 N23 119.54(13) . . ?
C6 N21 H21A 120.0 . . ?
C6 N21 H21B 120.0 . . ?
H21A N21 H21B 120.0 . . ?
C6 N22 H22A 120.0 . . ?
C6 N22 H22B 120.0 . . ?
H22A N22 H22B 120.0 . . ?
C6 N23 H23A 120.0 . . ?
C6 N23 H23B 120.0 . . ?
H23A N23 H23B 120.0 . . ?
N25 C7 N24 120.13(13) . . ?
N25 C7 N26 120.53(13) . . ?
N24 C7 N26 119.34(13) . . ?
C7 N24 H24A 120.0 . . ?
C7 N24 H24B 120.0 . . ?
H24A N24 H24B 120.0 . . ?
C7 N25 H25A 120.0 . . ?
C7 N25 H25B 120.0 . . ?
H25A N25 H25B 120.0 . . ?
C7 N26 H26A 120.0 . . ?
C7 N26 H26B 120.0 . . ?
H26A N26 H26B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N10 C3 N1 C1 -16.0(2) . . . . ?
N13 C3 N1 C1 167.28(12) . . . . ?
N2 C1 N1 C3 -17.4(2) . . . . ?
N5 C1 N1 C3 166.98(12) . . . . ?
N1 C1 N2 N3 -175.40(14) . . . . ?
N5 C1 N2 N3 0.81(14) . . . . ?
C1 N2 N3 N4 -0.37(16) . . . . ?
N2 N3 N4 N5 -0.25(16) . . . . ?
N3 N4 N5 C1 0.77(15) . . . . ?
N3 N4 N5 C2 -179.48(12) . . . . ?
N1 C1 N5 N4 175.60(12) . . . . ?
N2 C1 N5 N4 -0.99(14) . . . . ?
N1 C1 N5 C2 -4.1(2) . . . . ?
N2 C1 N5 C2 179.31(13) . . . . ?
N9 C2 N5 N4 172.12(12) . . . . ?
N6 C2 N5 N4 -7.67(19) . . . . ?
N9 C2 N5 C1 -8.2(2) . . . . ?
N6 C2 N5 C1 172.01(14) . . . . ?
N9 C2 N6 N7 0.25(17) . . . . ?
N5 C2 N6 N7 -179.93(12) . . . . ?
C2 N6 N7 N8 0.00(18) . . . . ?
N6 N7 N8 N9 -0.23(18) . . . . ?
N6 C2 N9 N8 -0.39(17) . . . . ?
N5 C2 N9 N8 179.81(13) . . . . ?
N7 N8 N9 C2 0.37(17) . . . . ?
N1 C3 N10 N11 -176.12(14) . . . . ?
N13 C3 N10 N11 1.02(15) . . . . ?
C3 N10 N11 N12 -0.54(18) . . . . ?
N10 N11 N12 N13 -0.20(18) . . . . ?
N11 N12 N13 C3 0.86(16) . . . . ?
N11 N12 N13 C4 -177.19(12) . . . . ?
N1 C3 N13 N12 176.26(12) . . . . ?
N10 C3 N13 N12 -1.18(15) . . . . ?
N1 C3 N13 C4 -6.1(2) . . . . ?
N10 C3 N13 C4 176.46(13) . . . . ?
N17 C4 N13 N12 179.56(13) . . . . ?
N14 C4 N13 N12 0.91(19) . . . . ?
N17 C4 N13 C3 2.1(2) . . . . ?
N14 C4 N13 C3 -176.56(14) . . . . ?
N17 C4 N14 N15 0.92(17) . . . . ?
N13 C4 N14 N15 179.71(12) . . . . ?
C4 N14 N15 N16 -0.47(17) . . . . ?
N14 N15 N16 N17 -0.10(18) . . . . ?
N14 C4 N17 N16 -0.97(17) . . . . ?
N13 C4 N17 N16 -179.70(13) . . . . ?
N15 N16 N17 C4 0.63(17) . . . . ?

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
N18 H18A N9 0.86 2.16 2.9978(17) 164.8 . yes
N18 H18B N14 0.86 2.57 3.2838(17) 141.5 2_666 yes
N18 H18B N15 0.86 2.56 3.3879(18) 161.2 2_666 yes
N19 H19A N8 0.86 2.05 2.8997(17) 169.2 . yes
N19 H19B N3 0.86 2.47 3.2019(17) 143.7 1_465 yes
N20 H20A N2 0.86 2.38 3.0976(17) 141.2 1_465 yes
N20 H20A N26 0.86 2.57 3.1461(18) 125.4 2_676 yes
N20 H20B N14 0.86 2.13 2.9522(17) 160.5 2_666 yes
N21 H21A N4 0.86 2.29 3.1153(16) 161.8 2_765 yes
N21 H21B N17 0.86 2.11 2.9521(17) 166.3 . yes
N22 H22A N3 0.86 2.22 3.0592(17) 165.1 2_765 yes
N22 H22B N2 0.86 2.39 3.1420(17) 146.8 1_565 yes
N23 H23A N16 0.86 2.30 3.1347(19) 162.3 . yes
N23 H23B N10 0.86 2.29 3.0851(18) 152.9 1_565 yes
N23 H23B N11 0.86 2.65 3.3240(18) 135.8 1_565 yes
N24 H24A N15 0.86 2.45 3.2125(19) 148.4 . yes
N24 H24A N16 0.86 2.14 2.9886(17) 167.4 . yes
N24 H24B N11 0.86 2.04 2.9021(18) 176.7 1_565 yes
N25 H25A N15 0.86 2.37 3.1547(17) 151.6 . yes
N25 H25B N6 0.86 2.13 2.9465(18) 157.7 1_556 yes
N26 H26B N12 0.86 2.65 3.4667(18) 159.2 1_565 yes
N26 H26B N20 0.86 2.66 3.1461(18) 116.8 2_676 yes
N26 H26A N6 0.86 2.58 3.2842(18) 139.6 1_556 yes
N26 H26A N7 0.86 2.24 3.0860(19) 166.5 1_556 yes

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_LYF201221_2_a
_database_code_depnum_ccdc_archive 'CCDC 2051824'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00674F 2021
loop_
_audit_author_name
_audit_author_address
'YiFei Liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 N17 Na, H2 O, 2(H4 N)'
_chemical_formula_sum            'C4 H10 N19 Na O'
_chemical_formula_weight         363.30

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5686(11)
_cell_length_b                   9.5808(10)
_cell_length_c                   9.5851(11)
_cell_angle_alpha                81.051(3)
_cell_angle_beta                 81.699(3)
_cell_angle_gamma                60.468(3)
_cell_volume                     752.90(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4548
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_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            9792
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.454
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3401
_reflns_number_gt                2459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+0.1895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3401
_refine_ls_number_parameters     260
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.048
_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
C1 C 0.27464(19) 0.5660(2) 0.48962(18) 0.0239(4) Uani 1 1 d . . . . .
C2 C 0.1956(2) 0.3480(2) 0.56886(18) 0.0263(4) Uani 1 1 d . . . . .
C3 C 0.4512(2) 0.5767(2) 0.30460(18) 0.0261(4) Uani 1 1 d . . . . .
C4 C 0.6324(2) 0.3658(2) 0.13637(18) 0.0288(4) Uani 1 1 d . . . . .
N1 N 0.38470(17) 0.49312(17) 0.38414(15) 0.0270(3) Uani 1 1 d . . . . .
N2 N 0.22145(18) 0.70929(17) 0.53807(16) 0.0302(4) Uani 1 1 d . . . . .
N3 N 0.10843(19) 0.72115(18) 0.64613(17) 0.0342(4) Uani 1 1 d . . . . .
N4 N 0.08929(18) 0.59617(18) 0.66863(16) 0.0337(4) Uani 1 1 d . . . . .
N5 N 0.19433(17) 0.49392(17) 0.57204(15) 0.0270(3) Uani 1 1 d . . . . .
N6 N 0.07887(19) 0.32137(19) 0.63696(18) 0.0381(4) Uani 1 1 d . . . . .
N7 N 0.1261(2) 0.1694(2) 0.6112(2) 0.0423(4) Uani 1 1 d . . . . .
N8 N 0.2617(2) 0.11207(19) 0.53265(19) 0.0397(4) Uani 1 1 d . . . . .
N9 N 0.31031(19) 0.22527(18) 0.50334(18) 0.0354(4) Uani 1 1 d . . . . .
N10 N 0.43098(19) 0.72435(18) 0.31186(16) 0.0327(4) Uani 1 1 d . . . . .
N11 N 0.5270(2) 0.7500(2) 0.20287(17) 0.0387(4) Uani 1 1 d . . . . .
N12 N 0.6058(2) 0.6279(2) 0.13067(17) 0.0383(4) Uani 1 1 d . . . . .
N13 N 0.56239(18) 0.51515(18) 0.19294(15) 0.0290(3) Uani 1 1 d . . . . .
N14 N 0.7263(2) 0.3400(2) 0.01726(17) 0.0421(4) Uani 1 1 d . . . . .
N15 N 0.7716(2) 0.1854(2) 0.00188(19) 0.0487(5) Uani 1 1 d . . . . .
N16 N 0.7065(2) 0.1264(2) 0.10587(18) 0.0473(5) Uani 1 1 d . . . . .
N17 N 0.6153(2) 0.2416(2) 0.19508(17) 0.0419(4) Uani 1 1 d . . . . .
N18 N 0.9204(2) 0.04058(19) 0.74108(18) 0.0364(4) Uani 1 1 d D . . . .
H18A H 0.991(2) 0.077(2) 0.704(2) 0.055 Uiso 1 1 d D U . . .
H18B H 0.964(2) -0.0659(17) 0.743(2) 0.055 Uiso 1 1 d D U . . .
H18C H 0.836(2) 0.089(2) 0.6877(18) 0.055 Uiso 1 1 d D U . . .
H18D H 0.887(2) 0.070(2) 0.8299(16) 0.055 Uiso 1 1 d D U . . .
N19 N 0.7849(2) 0.5867(2) 0.82440(19) 0.0494(5) Uani 1 1 d D . . . .
H19A H 0.760(3) 0.683(2) 0.858(2) 0.074 Uiso 1 1 d D U . . .
H19B H 0.777(3) 0.513(2) 0.898(2) 0.074 Uiso 1 1 d D U . . .
H19C H 0.715(2) 0.606(3) 0.757(2) 0.074 Uiso 1 1 d D U . . .
H19D H 0.890(2) 0.540(3) 0.783(2) 0.074 Uiso 1 1 d D U . . .
Na1 Na 0.58380(8) 0.18234(8) 0.45088(7) 0.0312(2) Uani 1 1 d . . . . .
O1A O 0.8569(14) 0.7835(12) 0.9928(11) 0.104(3) Uani 0.254(5) 1 d . U P A 1
H1AA H 0.910099 0.718726 0.930014 0.156 Uiso 0.254(5) 1 d R U P A 1
H1AB H 0.881789 0.725036 1.071003 0.156 Uiso 0.254(5) 1 d R U P A 1
O1B O 0.6959(4) 0.8970(3) 0.9119(3) 0.0893(11) Uani 0.746(5) 1 d . U P A 2
H1BB H 0.782018 0.900059 0.918426 0.134 Uiso 0.746(5) 1 d R U P A 2
H1BA H 0.641989 0.969529 0.848656 0.134 Uiso 0.746(5) 1 d R U P A 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
C1 N2 1.342(2) . ?
C1 N1 1.344(2) . ?
C1 N5 1.367(2) . ?
C2 N9 1.319(2) . ?
C2 N6 1.325(2) . ?
C2 N5 1.397(2) . ?
C3 N1 1.341(2) . ?
C3 N10 1.342(2) . ?
C3 N13 1.369(2) . ?
C4 N17 1.311(2) . ?
C4 N14 1.321(2) . ?
C4 N13 1.407(2) . ?
N1 Na1 2.6592(16) . ?
N2 N3 1.359(2) . ?
N2 Na1 2.5613(17) 2_666 ?
N3 N4 1.280(2) . ?
N4 N5 1.3674(19) . ?
N6 N7 1.347(2) . ?
N7 N8 1.303(2) . ?
N8 N9 1.355(2) . ?
N8 Na1 2.4463(17) 2_656 ?
N9 Na1 2.4277(17) . ?
N10 N11 1.364(2) . ?
N10 Na1 2.5309(17) 2_666 ?
N11 N12 1.283(2) . ?
N12 N13 1.366(2) . ?
N14 N15 1.349(2) . ?
N15 N16 1.301(2) . ?
N16 N17 1.356(2) . ?
N17 Na1 2.4386(18) . ?
N18 H18A 0.906(14) . ?
N18 H18B 0.890(14) . ?
N18 H18C 0.897(14) . ?
N18 H18D 0.902(14) . ?
N19 H19A 0.929(15) . ?
N19 H19B 0.935(16) . ?
N19 H19C 0.936(15) . ?
N19 H19D 0.929(16) . ?
O1A H1AA 0.8501 . ?
O1A H1AB 0.8500 . ?
O1B H1BB 0.8501 . ?
O1B H1BA 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
N2 C1 N1 131.59(16) . . ?
N2 C1 N5 106.71(14) . . ?
N1 C1 N5 121.70(15) . . ?
N9 C2 N6 114.19(16) . . ?
N9 C2 N5 124.68(16) . . ?
N6 C2 N5 121.11(15) . . ?
N1 C3 N10 131.51(15) . . ?
N1 C3 N13 122.13(16) . . ?
N10 C3 N13 106.36(15) . . ?
N17 C4 N14 114.28(16) . . ?
N17 C4 N13 124.83(15) . . ?
N14 C4 N13 120.88(17) . . ?
C3 N1 C1 117.30(15) . . ?
C3 N1 Na1 115.94(10) . . ?
C1 N1 Na1 114.02(11) . . ?
C1 N2 N3 106.17(14) . . ?
C1 N2 Na1 120.45(11) . 2_666 ?
N3 N2 Na1 121.24(11) . 2_666 ?
N4 N3 N2 112.41(14) . . ?
N3 N4 N5 105.91(14) . . ?
N4 N5 C1 108.79(14) . . ?
N4 N5 C2 118.49(14) . . ?
C1 N5 C2 132.62(14) . . ?
C2 N6 N7 102.76(14) . . ?
N8 N7 N6 110.51(15) . . ?
N7 N8 N9 109.20(15) . . ?
N7 N8 Na1 114.68(12) . 2_656 ?
N9 N8 Na1 130.95(12) . 2_656 ?
C2 N9 N8 103.34(14) . . ?
C2 N9 Na1 123.08(12) . . ?
N8 N9 Na1 127.66(12) . . ?
C3 N10 N11 106.68(14) . . ?
C3 N10 Na1 120.27(11) . 2_666 ?
N11 N10 Na1 118.24(12) . 2_666 ?
N12 N11 N10 111.75(15) . . ?
N11 N12 N13 106.20(14) . . ?
N12 N13 C3 108.98(14) . . ?
N12 N13 C4 118.88(14) . . ?
C3 N13 C4 132.13(15) . . ?
C4 N14 N15 102.78(16) . . ?
N16 N15 N14 110.44(15) . . ?
N15 N16 N17 108.82(16) . . ?
C4 N17 N16 103.68(15) . . ?
C4 N17 Na1 123.02(12) . . ?
N16 N17 Na1 123.24(13) . . ?
H18A N18 H18B 112.1(14) . . ?
H18A N18 H18C 107.5(14) . . ?
H18B N18 H18C 109.7(14) . . ?
H18A N18 H18D 108.3(14) . . ?
H18B N18 H18D 109.7(14) . . ?
H18C N18 H18D 109.4(14) . . ?
H19A N19 H19B 111.6(15) . . ?
H19A N19 H19C 110.1(15) . . ?
H19B N19 H19C 108.6(15) . . ?
H19A N19 H19D 109.4(14) . . ?
H19B N19 H19D 108.1(15) . . ?
H19C N19 H19D 108.9(14) . . ?
N9 Na1 N17 105.92(7) . . ?
N9 Na1 N8 101.39(6) . 2_656 ?
N17 Na1 N8 99.40(6) . 2_656 ?
N9 Na1 N10 89.58(6) . 2_666 ?
N17 Na1 N10 144.25(6) . 2_666 ?
N8 Na1 N10 109.02(6) 2_656 2_666 ?
N9 Na1 N2 146.32(5) . 2_666 ?
N17 Na1 N2 85.17(6) . 2_666 ?
N8 Na1 N2 108.12(6) 2_656 2_666 ?
N10 Na1 N2 65.91(5) 2_666 2_666 ?
N9 Na1 N1 72.36(5) . . ?
N17 Na1 N1 71.60(5) . . ?
N8 Na1 N1 166.42(6) 2_656 . ?
N10 Na1 N1 83.33(5) 2_666 . ?
N2 Na1 N1 81.74(5) 2_666 . ?
H1AA O1A H1AB 104.5 . . ?
H1BB O1B H1BA 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N18 H18A N7 0.906(14) 1.953(14) 2.856(2) 174.5(18) 1_655 yes
N18 H18B N3 0.890(14) 2.089(15) 2.898(2) 150.6(17) 1_645 yes
N18 H18C N2 0.897(14) 2.592(17) 3.254(2) 131.3(15) 2_666 yes
N18 H18C N10 0.897(14) 2.285(16) 3.051(2) 143.1(16) 2_666 yes
N18 H18D N15 0.902(14) 2.000(14) 2.882(2) 165.5(18) 1_556 yes
N19 H19A O1A^a 0.929(15) 2.25(2) 3.031(9) 140.8(18) . yes
N19 H19A O1B^b 0.929(15) 1.963(15) 2.889(3) 175(2) . yes
N19 H19B N12 0.935(16) 2.61(2) 3.155(2) 117.7(16) 1_556 yes
N19 H19B N14 0.935(16) 2.087(16) 2.994(3) 163.2(19) 1_556 yes
N19 H19C N1 0.936(15) 2.297(17) 3.138(2) 149.4(18) 2_666 yes
N19 H19D N4 0.929(16) 2.315(18) 3.112(2) 143.7(18) 1_655 yes
N19 H19D N6 0.929(16) 2.463(19) 3.243(2) 141.6(17) 1_655 yes
O1A^a H1AA^a N19 0.85 2.51 3.031(9) 120.4 . yes
O1B^b H1BB^b N18 0.85 2.62 3.222(3) 129.2 1_565 yes
O1B^b H1BA^b N11 0.85 2.37 3.100(3) 144.3 2_676 yes

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_LYF201202_1_a
_database_code_depnum_ccdc_archive 'CCDC 2047779'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00674F 2021
loop_
_audit_author_name
_audit_author_address
'YiFei Liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-12-02 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 K12 N68 O9'
_chemical_formula_sum            'C16 H18 K12 N68 O9'
_chemical_formula_weight         1776.18

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.981(3)
_cell_length_b                   12.023(2)
_cell_length_c                   16.981(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.519(5)
_cell_angle_gamma                90
_cell_volume                     2960.8(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3672
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.992
_exptl_crystal_F_000             1780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.974
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_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            9225
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2551
_reflns_number_gt                1788
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+75.5839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2551
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0901
_refine_ls_wR_factor_ref         0.2289
_refine_ls_wR_factor_gt          0.2102
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.63842(15) 0.82304(19) 0.92917(13) 0.0454(6) Uani 1 1 d . . . . .
K2 K 0.61804(14) 0.82807(17) 0.51365(11) 0.0371(5) Uani 1 1 d . . . . .
K3 K 0.65607(16) 1.33280(17) 0.69038(13) 0.0431(6) Uani 1 1 d . . . . .
C1 C 0.6803(6) 0.6017(7) 0.8099(5) 0.031(2) Uani 1 1 d . . . . .
C2 C 0.5875(5) 0.7371(6) 0.7052(5) 0.0203(17) Uani 1 1 d . . . . .
C3 C 0.5834(5) 0.9252(7) 0.7038(5) 0.0252(18) Uani 1 1 d . . . . .
C4 C 0.6699(5) 1.0648(6) 0.8056(5) 0.0209(17) Uani 1 1 d . . . . .
N1 N 0.7275(6) 0.6669(7) 0.8636(5) 0.050(2) Uani 1 1 d . . . . .
N2 N 0.7814(5) 0.5967(8) 0.9194(5) 0.049(2) Uani 1 1 d . . . . .
N3 N 0.7632(6) 0.4951(7) 0.8949(5) 0.049(2) Uani 1 1 d . . . . .
N4 N 0.6991(6) 0.4948(7) 0.8245(5) 0.048(2) Uani 1 1 d . . . . .
N5 N 0.6158(5) 0.6353(5) 0.7390(4) 0.0254(16) Uani 1 1 d . . . . .
N6 N 0.5731(5) 0.5538(6) 0.6873(5) 0.0332(18) Uani 1 1 d . . . . .
N7 N 0.5217(6) 0.6016(6) 0.6266(5) 0.041(2) Uani 1 1 d . . . . .
N8 N 0.5271(5) 0.7149(6) 0.6341(4) 0.0318(17) Uani 1 1 d . . . . .
N9 N 0.6164(4) 0.8325(5) 0.7430(4) 0.0270(15) Uani 1 1 d . . . . .
N10 N 0.5223(5) 0.9417(5) 0.6306(4) 0.0281(17) Uani 1 1 d . . . . .
N11 N 0.5126(5) 1.0542(6) 0.6211(4) 0.0317(17) Uani 1 1 d . . . . .
N12 N 0.5616(5) 1.1088(6) 0.6809(4) 0.0288(17) Uani 1 1 d . . . . .
N13 N 0.6070(4) 1.0308(5) 0.7340(4) 0.0240(15) Uani 1 1 d . . . . .
N14 N 0.6894(6) 1.1710(6) 0.8203(4) 0.0393(19) Uani 1 1 d . . . . .
N15 N 0.7501(5) 1.1693(6) 0.8931(4) 0.0369(18) Uani 1 1 d . . . . .
N16 N 0.7656(5) 1.0685(6) 0.9190(5) 0.0383(19) Uani 1 1 d . . . . .
N17 N 0.7160(6) 0.9978(6) 0.8632(5) 0.043(2) Uani 1 1 d . . . . .
O1 O 0.5599(7) 0.6613(9) 0.3989(9) 0.128(5) Uani 1 1 d . . . . .
H1A H 0.603361 0.646909 0.376533 0.192 Uiso 1 1 d R U . . .
H1B H 0.513191 0.684490 0.363223 0.192 Uiso 1 1 d R U . . .
O2 O 0.6202(6) 1.3769(7) 0.5224(5) 0.082(3) Uani 1 1 d . . . . .
H2A H 0.643550 1.439517 0.515629 0.122 Uiso 1 1 d R U . . .
H2B H 0.562240 1.378919 0.502069 0.122 Uiso 1 1 d R U . . .
O3 O 0.500000 1.336(2) 0.750000 0.150(17) Uani 0.5 2 d S T P . .
H3A H 0.488890 1.398743 0.767820 0.224 Uiso 0.25 1 d R U P . .
H3B H 0.509120 1.288215 0.788400 0.224 Uiso 0.25 1 d R U P . .


_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 N1 2.701(10) . ?
K1 N2 2.728(9) 7_667 ?
K1 N10 2.764(7) 2_656 ?
K1 N8 2.767(8) 2_656 ?
K1 N17 2.770(8) . ?
K1 O2 2.929(9) 6_576 ?
K1 N9 3.098(7) . ?
K1 K1 4.002(4) 7_667 ?
K1 K3 4.092(3) 4_646 ?
K1 K2 4.193(3) 2_656 ?
K1 K2 4.468(3) 6_576 ?
K1 K3 4.761(3) 6_576 ?
K2 O1 2.779(10) . ?
K2 N3 2.867(8) 4_656 ?
K2 N15 2.913(7) 4_646 ?
K2 N11 2.970(7) 5_676 ?
K2 N8 3.047(8) . ?
K2 N10 3.050(8) . ?
K2 N15 3.183(8) 6_575 ?
K2 N16 3.285(9) 6_575 ?
K2 K2 4.504(4) 7_666 ?
K3 O3 2.771(2) . ?
K3 O2 2.818(9) . ?
K3 N14 2.889(8) . ?
K3 N6 2.929(7) 1_565 ?
K3 N4 2.943(8) 1_565 ?
K3 N1 2.943(9) 4_656 ?
K3 N12 3.028(7) . ?
K3 N17 3.050(9) 4_656 ?
K3 O1 3.211(12) 5_676 ?
K3 N9 3.311(7) 4_656 ?
K3 H1B 2.479(11) 5_676 ?
K3 H3A 2.573(9) 2_656 ?
K3 H3B 2.644(7) 2_656 ?
C1 N1 1.273(12) . ?
C1 N4 1.327(12) . ?
C1 N5 1.401(11) . ?
C2 N9 1.333(10) . ?
C2 N8 1.343(10) . ?
C2 N5 1.372(9) . ?
C3 N9 1.328(10) . ?
C3 N10 1.361(10) . ?
C3 N13 1.381(10) . ?
C4 N14 1.320(10) . ?
C4 N17 1.321(10) . ?
C4 N13 1.399(10) . ?
N1 N2 1.371(11) . ?
N2 N3 1.297(12) . ?
N3 N4 1.333(11) . ?
N5 N6 1.362(9) . ?
N6 N7 1.260(10) . ?
N7 N8 1.369(10) . ?
N10 N11 1.365(9) . ?
N11 N12 1.276(10) . ?
N12 N13 1.360(9) . ?
N14 N15 1.339(10) . ?
N15 N16 1.290(10) . ?
N16 N17 1.350(10) . ?
O1 H1A 0.8501 . ?
O1 H1B 0.8500 . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?
O3 H3A 0.8501 . ?
O3 H3B 0.8500 . ?
O3 H3A 0.8501 2_656 ?
O3 H3B 0.8499 2_656 ?

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
N1 K1 N2 119.3(3) . 7_667 ?
N1 K1 N10 133.0(2) . 2_656 ?
N2 K1 N10 107.5(2) 7_667 2_656 ?
N1 K1 N8 90.0(2) . 2_656 ?
N2 K1 N8 132.2(3) 7_667 2_656 ?
N10 K1 N8 59.1(2) 2_656 2_656 ?
N1 K1 N17 93.4(3) . . ?
N2 K1 N17 89.0(2) 7_667 . ?
N10 K1 N17 82.8(2) 2_656 . ?
N8 K1 N17 128.7(2) 2_656 . ?
N1 K1 O2 77.0(3) . 6_576 ?
N2 K1 O2 81.9(2) 7_667 6_576 ?
N10 K1 O2 115.6(3) 2_656 6_576 ?
N8 K1 O2 68.2(2) 2_656 6_576 ?
N17 K1 O2 161.2(3) . 6_576 ?
N1 K1 N9 62.7(2) . . ?
N2 K1 N9 149.1(2) 7_667 . ?
N10 K1 N9 75.3(2) 2_656 . ?
N8 K1 N9 76.4(2) 2_656 . ?
N17 K1 N9 60.5(2) . . ?
O2 K1 N9 125.6(2) 6_576 . ?
N1 K1 K1 61.19(18) . 7_667 ?
N2 K1 K1 58.98(19) 7_667 7_667 ?
N10 K1 K1 165.23(18) 2_656 7_667 ?
N8 K1 K1 124.02(18) 2_656 7_667 ?
N17 K1 K1 101.76(18) . 7_667 ?
O2 K1 K1 59.47(18) 6_576 7_667 ?
N9 K1 K1 119.27(15) . 7_667 ?
N1 K1 K3 45.91(18) . 4_646 ?
N2 K1 K3 104.45(19) 7_667 4_646 ?
N10 K1 K3 119.82(17) 2_656 4_646 ?
N8 K1 K3 122.22(17) 2_656 4_646 ?
N17 K1 K3 48.18(19) . 4_646 ?
O2 K1 K3 118.4(2) 6_576 4_646 ?
N9 K1 K3 52.66(13) . 4_646 ?
K1 K1 K3 72.05(7) 7_667 4_646 ?
N1 K1 K2 132.99(19) . 2_656 ?
N2 K1 K2 89.36(19) 7_667 2_656 ?
N10 K1 K2 46.62(16) 2_656 2_656 ?
N8 K1 K2 46.58(16) 2_656 2_656 ?
N17 K1 K2 125.8(2) . 2_656 ?
O2 K1 K2 70.8(2) 6_576 2_656 ?
N9 K1 K2 111.50(14) . 2_656 ?
K1 K1 K2 122.89(9) 7_667 2_656 ?
K3 K1 K2 164.05(7) 4_646 2_656 ?
N1 K1 K2 149.97(19) . 6_576 ?
N2 K1 K2 54.15(19) 7_667 6_576 ?
N10 K1 K2 60.65(14) 2_656 6_576 ?
N8 K1 K2 116.03(16) 2_656 6_576 ?
N17 K1 K2 59.17(19) . 6_576 ?
O2 K1 K2 125.0(2) 6_576 6_576 ?
N9 K1 K2 107.15(14) . 6_576 ?
K1 K1 K2 109.45(8) 7_667 6_576 ?
K3 K1 K2 104.65(6) 4_646 6_576 ?
K2 K1 K2 76.81(6) 2_656 6_576 ?
N1 K1 K3 101.13(18) . 6_576 ?
N2 K1 K3 49.63(18) 7_667 6_576 ?
N10 K1 K3 112.66(17) 2_656 6_576 ?
N8 K1 K3 90.68(16) 2_656 6_576 ?
N17 K1 K3 138.11(16) . 6_576 ?
O2 K1 K3 33.31(17) 6_576 6_576 ?
N9 K1 K3 158.79(14) . 6_576 ?
K1 K1 K3 54.85(6) 7_667 6_576 ?
K3 K1 K3 126.91(6) 4_646 6_576 ?
K2 K1 K3 68.28(5) 2_656 6_576 ?
K2 K1 K3 93.59(5) 6_576 6_576 ?
O1 K2 N3 158.1(3) . 4_656 ?
O1 K2 N15 87.6(3) . 4_646 ?
N3 K2 N15 85.4(3) 4_656 4_646 ?
O1 K2 N11 76.9(3) . 5_676 ?
N3 K2 N11 106.5(2) 4_656 5_676 ?
N15 K2 N11 163.1(2) 4_646 5_676 ?
O1 K2 N8 92.0(3) . . ?
N3 K2 N8 105.7(2) 4_656 . ?
N15 K2 N8 72.5(2) 4_646 . ?
N11 K2 N8 114.2(2) 5_676 . ?
O1 K2 N10 131.6(3) . . ?
N3 K2 N10 70.3(2) 4_656 . ?
N15 K2 N10 107.8(2) 4_646 . ?
N11 K2 N10 87.78(19) 5_676 . ?
N8 K2 N10 53.16(18) . . ?
O1 K2 N15 72.1(3) . 6_575 ?
N3 K2 N15 86.6(2) 4_656 6_575 ?
N15 K2 N15 84.8(2) 4_646 6_575 ?
N11 K2 N15 84.0(2) 5_676 6_575 ?
N8 K2 N15 152.9(2) . 6_575 ?
N10 K2 N15 152.1(2) . 6_575 ?
O1 K2 N16 93.5(3) . 6_575 ?
N3 K2 N16 66.3(2) 4_656 6_575 ?
N15 K2 N16 93.8(2) 4_646 6_575 ?
N11 K2 N16 80.6(2) 5_676 6_575 ?
N8 K2 N16 165.0(2) . 6_575 ?
N10 K2 N16 129.27(19) . 6_575 ?
N15 K2 N16 22.93(18) 6_575 6_575 ?
O1 K2 K1 90.4(2) . 2_656 ?
N3 K2 K1 111.39(19) 4_656 2_656 ?
N15 K2 K1 113.62(17) 4_646 2_656 ?
N11 K2 K1 73.74(15) 5_676 2_656 ?
N8 K2 K1 41.26(14) . 2_656 ?
N10 K2 K1 41.20(13) . 2_656 ?
N15 K2 K1 154.47(15) 6_575 2_656 ?
N16 K2 K1 152.46(15) 6_575 2_656 ?
O1 K2 K1 119.1(3) . 6_575 ?
N3 K2 K1 55.5(2) 4_656 6_575 ?
N15 K2 K1 134.28(17) 4_646 6_575 ?
N11 K2 K1 52.44(14) 5_676 6_575 ?
N8 K2 K1 135.44(15) . 6_575 ?
N10 K2 K1 82.51(13) . 6_575 ?
N15 K2 K1 71.38(14) 6_575 6_575 ?
N16 K2 K1 51.63(14) 6_575 6_575 ?
K1 K2 K1 103.19(6) 2_656 6_575 ?
O1 K2 K2 75.9(2) . 7_666 ?
N3 K2 K2 84.6(2) 4_656 7_666 ?
N15 K2 K2 44.74(16) 4_646 7_666 ?
N11 K2 K2 123.05(17) 5_676 7_666 ?
N8 K2 K2 115.77(15) . 7_666 ?
N10 K2 K2 145.30(15) . 7_666 ?
N15 K2 K2 40.09(13) 6_575 7_666 ?
N16 K2 K2 52.55(14) 6_575 7_666 ?
K1 K2 K2 153.74(9) 2_656 7_666 ?
K1 K2 K2 103.05(7) 6_575 7_666 ?
O3 K3 O2 113.8(3) . . ?
O3 K3 N14 74.3(4) . . ?
O2 K3 N14 148.5(2) . . ?
O3 K3 N6 66.6(6) . 1_565 ?
O2 K3 N6 80.7(2) . 1_565 ?
N14 K3 N6 128.0(2) . 1_565 ?
O3 K3 N4 75.6(4) . 1_565 ?
O2 K3 N4 127.5(2) . 1_565 ?
N14 K3 N4 83.8(2) . 1_565 ?
N6 K3 N4 54.8(2) 1_565 1_565 ?
O3 K3 N1 137.9(6) . 4_656 ?
O2 K3 N1 77.9(3) . 4_656 ?
N14 K3 N1 77.2(3) . 4_656 ?
N6 K3 N1 153.1(3) 1_565 4_656 ?
N4 K3 N1 131.1(2) 1_565 4_656 ?
O3 K3 N12 66.7(6) . . ?
O2 K3 N12 98.4(2) . . ?
N14 K3 N12 55.31(19) . . ?
N6 K3 N12 128.0(2) 1_565 . ?
N4 K3 N12 129.7(2) 1_565 . ?
N1 K3 N12 71.7(2) 4_656 . ?
O3 K3 N17 138.7(6) . 4_656 ?
O2 K3 N17 63.3(2) . 4_656 ?
N14 K3 N17 131.6(2) . 4_656 ?
N6 K3 N17 72.6(2) 1_565 4_656 ?
N4 K3 N17 76.6(2) 1_565 4_656 ?
N1 K3 N17 83.3(2) 4_656 4_656 ?
N12 K3 N17 152.0(2) . 4_656 ?
O3 K3 O1 47.9(3) . 5_676 ?
O2 K3 O1 66.6(3) . 5_676 ?
N14 K3 O1 109.7(3) . 5_676 ?
N6 K3 O1 66.3(2) 1_565 5_676 ?
N4 K3 O1 110.5(3) 1_565 5_676 ?
N1 K3 O1 118.3(2) 4_656 5_676 ?
N12 K3 O1 66.0(2) . 5_676 ?
N17 K3 O1 118.6(3) 4_656 5_676 ?
O3 K3 N9 139.97(14) . 4_656 ?
O2 K3 N9 105.4(2) . 4_656 ?
N14 K3 N9 76.8(2) . 4_656 ?
N6 K3 N9 113.77(19) 1_565 4_656 ?
N4 K3 N9 74.3(2) 1_565 4_656 ?
N1 K3 N9 57.7(2) 4_656 4_656 ?
N12 K3 N9 116.39(18) . 4_656 ?
N17 K3 N9 55.45(18) 4_656 4_656 ?
O1 K3 N9 172.0(3) 5_676 4_656 ?
O3 K3 K1 171.94(11) . 4_656 ?
O2 K3 K1 58.6(2) . 4_656 ?
N14 K3 K1 110.61(18) . 4_656 ?
N6 K3 K1 112.71(16) 1_565 4_656 ?
N4 K3 K1 110.9(2) 1_565 4_656 ?
N1 K3 K1 41.2(2) 4_656 4_656 ?
N12 K3 K1 110.35(15) . 4_656 ?
N17 K3 K1 42.60(15) 4_656 4_656 ?
O1 K3 K1 124.1(3) 5_676 4_656 ?
N9 K3 K1 48.05(12) 4_656 4_656 ?
O3 K3 K1 119.3(3) . 6_575 ?
O2 K3 K1 34.81(19) . 6_575 ?
N14 K3 K1 113.90(16) . 6_575 ?
N6 K3 K1 114.61(16) 1_565 6_575 ?
N4 K3 K1 158.72(19) 1_565 6_575 ?
N1 K3 K1 48.86(16) 4_656 6_575 ?
N12 K3 K1 71.60(14) . 6_575 ?
N17 K3 K1 82.56(15) 4_656 6_575 ?
O1 K3 K1 75.8(2) 5_676 6_575 ?
N9 K3 K1 97.47(13) 4_656 6_575 ?
K1 K3 K1 53.09(6) 4_656 6_575 ?
O3 K3 H1B 41.9(3) . 5_676 ?
O2 K3 H1B 74.1(4) . 5_676 ?
N14 K3 H1B 100.9(4) . 5_676 ?
N6 K3 H1B 71.3(3) 1_565 5_676 ?
N4 K3 H1B 110.2(3) 1_565 5_676 ?
N1 K3 H1B 117.4(3) 4_656 5_676 ?
N12 K3 H1B 59.0(3) . 5_676 ?
N17 K3 H1B 127.3(4) 4_656 5_676 ?
O1 K3 H1B 8.76(9) 5_676 5_676 ?
N9 K3 H1B 174.9(3) 4_656 5_676 ?
K1 K3 H1B 130.0(3) 4_656 5_676 ?
K1 K3 H1B 79.2(3) 6_575 5_676 ?
O3 K3 H3A 17.81(2) . 2_656 ?
O2 K3 H3A 105.1(3) . 2_656 ?
N14 K3 H3A 89.6(5) . 2_656 ?
N6 K3 H3A 48.8(6) 1_565 2_656 ?
N4 K3 H3A 67.6(4) 1_565 2_656 ?
N1 K3 H3A 154.4(6) 4_656 2_656 ?
N12 K3 H3A 82.7(6) . 2_656 ?
N17 K3 H3A 121.2(6) 4_656 2_656 ?
O1 K3 H3A 45.8(3) 5_676 2_656 ?
N9 K3 H3A 140.7(3) 4_656 2_656 ?
K1 K3 H3A 159.6(5) 4_656 2_656 ?
K1 K3 H3A 121.64(19) 6_575 2_656 ?
H1B K3 H3A 43.2 5_676 2_656 ?
O3 K3 H3B 17.860(15) . 2_656 ?
O2 K3 H3B 103.2(2) . 2_656 ?
N14 K3 H3B 75.4(4) . 2_656 ?
N6 K3 H3B 77.2(6) 1_565 2_656 ?
N4 K3 H3B 93.4(4) 1_565 2_656 ?
N1 K3 H3B 123.6(6) 4_656 2_656 ?
N12 K3 H3B 52.1(6) . 2_656 ?
N17 K3 H3B 148.4(6) 4_656 2_656 ?
O1 K3 H3B 37.1(3) 5_676 2_656 ?
N9 K3 H3B 150.7(3) 4_656 2_656 ?
K1 K3 H3B 155.3(3) 4_656 2_656 ?
K1 K3 H3B 102.2(3) 6_575 2_656 ?
H1B K3 H3B 29.2 5_676 2_656 ?
H3A K3 H3B 30.8 2_656 2_656 ?
N1 C1 N4 114.1(8) . . ?
N1 C1 N5 125.3(8) . . ?
N4 C1 N5 120.5(8) . . ?
N9 C2 N8 131.9(7) . . ?
N9 C2 N5 122.6(7) . . ?
N8 C2 N5 105.5(6) . . ?
N9 C3 N10 131.3(7) . . ?
N9 C3 N13 123.8(7) . . ?
N10 C3 N13 104.8(7) . . ?
N14 C4 N17 113.6(7) . . ?
N14 C4 N13 121.1(7) . . ?
N17 C4 N13 125.3(7) . . ?
C1 N1 N2 104.0(8) . . ?
C1 N1 K1 118.7(7) . . ?
N2 N1 K1 114.1(7) . . ?
C1 N1 K3 117.4(6) . 4_646 ?
N2 N1 K3 109.9(6) . 4_646 ?
K1 N1 K3 92.9(3) . 4_646 ?
N3 N2 N1 108.5(8) . . ?
N3 N2 K1 130.0(6) . 7_667 ?
N1 N2 K1 118.5(7) . 7_667 ?
N2 N3 N4 109.7(7) . . ?
N2 N3 K2 115.7(6) . 4_646 ?
N4 N3 K2 133.9(6) . 4_646 ?
C1 N4 N3 103.7(8) . . ?
C1 N4 K3 120.1(6) . 1_545 ?
N3 N4 K3 131.7(6) . 1_545 ?
N6 N5 C2 109.0(6) . . ?
N6 N5 C1 117.3(7) . . ?
C2 N5 C1 133.6(7) . . ?
N7 N6 N5 106.9(7) . . ?
N7 N6 K3 126.7(6) . 1_545 ?
N5 N6 K3 120.8(5) . 1_545 ?
N6 N7 N8 111.6(7) . . ?
C2 N8 N7 106.9(7) . . ?
C2 N8 K1 126.4(5) . 2_656 ?
N7 N8 K1 113.9(5) . 2_656 ?
C2 N8 K2 101.6(5) . . ?
N7 N8 K2 114.1(6) . . ?
K1 N8 K2 92.2(2) 2_656 . ?
C3 N9 C2 116.5(6) . . ?
C3 N9 K1 118.2(5) . . ?
C2 N9 K1 113.4(5) . . ?
C3 N9 K3 113.1(5) . 4_646 ?
C2 N9 K3 110.3(5) . 4_646 ?
K1 N9 K3 79.29(15) . 4_646 ?
C3 N10 N11 106.3(7) . . ?
C3 N10 K1 125.8(5) . 2_656 ?
N11 N10 K1 114.3(5) . 2_656 ?
C3 N10 K2 102.2(5) . . ?
N11 N10 K2 114.8(5) . . ?
K1 N10 K2 92.2(2) 2_656 . ?
N12 N11 N10 113.1(7) . . ?
N12 N11 K2 120.3(5) . 5_676 ?
N10 N11 K2 126.4(5) . 5_676 ?
N11 N12 N13 105.4(6) . . ?
N11 N12 K3 131.9(5) . . ?
N13 N12 K3 115.4(5) . . ?
N12 N13 C3 110.4(6) . . ?
N12 N13 C4 119.4(6) . . ?
C3 N13 C4 130.2(7) . . ?
C4 N14 N15 103.1(7) . . ?
C4 N14 K3 121.2(5) . . ?
N15 N14 K3 131.6(5) . . ?
N16 N15 N14 110.6(7) . . ?
N16 N15 K2 113.0(5) . 4_656 ?
N14 N15 K2 134.6(6) . 4_656 ?
N16 N15 K2 83.0(5) . 6_576 ?
N14 N15 K2 101.9(5) . 6_576 ?
K2 N15 K2 95.2(2) 4_656 6_576 ?
N15 N16 N17 109.4(7) . . ?
N15 N16 K2 74.1(5) . 6_576 ?
N17 N16 K2 105.3(6) . 6_576 ?
C4 N17 N16 103.3(7) . . ?
C4 N17 K1 124.6(6) . . ?
N16 N17 K1 114.0(5) . . ?
C4 N17 K3 115.3(6) . 4_646 ?
N16 N17 K3 110.1(6) . 4_646 ?
K1 N17 K3 89.2(2) . 4_646 ?
K2 O1 K3 114.6(3) . 5_676 ?
K2 O1 H1A 108.6 . . ?
K3 O1 H1A 126.0 5_676 . ?
K2 O1 H1B 108.7 . . ?
K3 O1 H1B 26.4 5_676 . ?
H1A O1 H1B 109.5 . . ?
K3 O2 K1 111.9(3) . 6_575 ?
K3 O2 H2A 108.8 . . ?
K1 O2 H2A 123.8 6_575 . ?
K3 O2 H2B 109.4 . . ?
K1 O2 H2B 91.6 6_575 . ?
H2A O2 H2B 109.5 . . ?
K3 O3 K3 178.7(12) . 2_656 ?
K3 O3 H3A 113.5 . . ?
K3 O3 H3A 67.8 2_656 . ?
K3 O3 H3B 106.5 . . ?
K3 O3 H3B 72.5 2_656 . ?
H3A O3 H3B 109.5 . . ?
K3 O3 H3A 67.8(6) . 2_656 ?
K3 O3 H3A 113.5(6) 2_656 2_656 ?
H3A O3 H3A 53.1 . 2_656 ?
H3B O3 H3A 149.7 . 2_656 ?
K3 O3 H3B 72.5(4) . 2_656 ?
K3 O3 H3B 106.5(4) 2_656 2_656 ?
H3A O3 H3B 149.7 . 2_656 ?
H3B O3 H3B 96.0 . 2_656 ?
H3A O3 H3B 109.5 2_656 2_656 ?

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 N4 0.85 2.52 3.284(13) 149.3 6_565 yes
O1 H1B O3 0.85 1.90 2.463(15) 122.6 5_676 yes
O2 H2A N16 0.85 2.18 2.893(12) 142.1 4_656 yes
O2 H2A N17 0.85 2.64 3.085(11) 113.8 4_656 yes
O2 H2B N7 0.85 2.24 2.879(11) 131.6 5_676 yes
O2 H2B N8 0.85 2.62 3.195(10) 126.2 5_676 yes
O3 H3A N6 0.85 2.30 3.13(3) 167.4 2_666 yes
O3 H3B N12 0.85 2.52 3.19(3) 137.5 2_656 yes
O3 H3B O1 0.85 1.94 2.463(15) 118.8 6_576 yes

_refine_diff_density_max         0.691
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.127

####################################################################### 
# 
# 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_LYF210322_a
_database_code_depnum_ccdc_archive 'CCDC 2072406'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00674F 2021
loop_
_audit_author_name
_audit_author_address
'YiFei Liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 N17, 2(C2 H6 O S)'
_chemical_formula_sum            'C8 H15 N17 O2 S2'
_chemical_formula_weight         445.49

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   13.226(2)
_cell_length_b                   10.403(2)
_cell_length_c                   7.7069(15)
_cell_angle_alpha                90
_cell_angle_beta                 117.138(5)
_cell_angle_gamma                90
_cell_volume                     943.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3245
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6417
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_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            4186
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.613
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_point_group_measured_fraction_full 0.839
_reflns_number_total             1758
_reflns_number_gt                1651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.574
_reflns_Friedel_fraction_max     0.630
_reflns_Friedel_fraction_full    0.672

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.1038P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1758
_refine_ls_number_parameters     135
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4556(2) 0.1775(3) 0.8245(3) 0.0346(6) Uani 1 1 d . . . . .
C2 C 0.4071(2) 0.3743(3) 0.6162(3) 0.0338(6) Uani 1 1 d . . . . .
C3 C 0.7241(3) 0.9564(3) 0.9013(5) 0.0520(8) Uani 1 1 d . . . . .
H3A H 0.793855 0.935094 1.013593 0.078 Uiso 1 1 calc R U . . .
H3B H 0.684301 1.020587 0.935986 0.078 Uiso 1 1 calc R U . . .
H3C H 0.740379 0.989156 0.800323 0.078 Uiso 1 1 calc R U . . .
C4 C 0.6434(3) 0.7664(3) 1.0390(5) 0.0529(8) Uani 1 1 d . . . . .
H4A H 0.602123 0.687321 1.019428 0.079 Uiso 1 1 calc R U . . .
H4B H 0.609724 0.831125 1.085059 0.079 Uiso 1 1 calc R U . . .
H4C H 0.721018 0.753426 1.133600 0.079 Uiso 1 1 calc R U . . .
N1 N 0.500000 0.2404(3) 1.000000 0.0370(7) Uani 1 2 d S T P . .
H1 H 0.500000 0.316(6) 1.000000 0.055 Uiso 1 2 d S U P . .
N2 N 0.4444(2) 0.0541(2) 0.7904(3) 0.0459(6) Uani 1 1 d . . . . .
N3 N 0.3945(3) 0.0431(3) 0.5897(4) 0.0538(7) Uani 1 1 d . . . . .
N4 N 0.3771(3) 0.1526(3) 0.5065(3) 0.0472(7) Uani 1 1 d . . . . .
N5 N 0.4157(2) 0.2422(2) 0.6533(3) 0.0361(6) Uani 1 1 d . . . . .
N6 N 0.3594(2) 0.4257(2) 0.4411(3) 0.0424(6) Uani 1 1 d . . . . .
N7 N 0.3740(2) 0.5493(2) 0.4857(3) 0.0423(6) Uani 1 1 d . . . . .
H7 H 0.350830 0.608731 0.398558 0.051 Uiso 1 1 calc R U . . .
N8 N 0.4260(3) 0.5739(2) 0.6718(3) 0.0489(6) Uani 1 1 d . . . . .
N9 N 0.4498(3) 0.4589(2) 0.7614(3) 0.0479(6) Uani 1 1 d . . . . .
O1 O 0.71419(19) 0.7211(2) 0.7787(3) 0.0534(6) Uani 1 1 d . . . . .
S1 S 0.63821(5) 0.81656(7) 0.81620(8) 0.0411(2) 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
C1 N2 1.305(4) . ?
C1 N5 1.356(3) . ?
C1 N1 1.371(3) . ?
C2 N6 1.314(3) . ?
C2 N9 1.330(4) . ?
C2 N5 1.397(3) . ?
C3 S1 1.777(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 S1 1.766(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1 0.78(6) . ?
N2 N3 1.382(3) . ?
N3 N4 1.275(4) . ?
N4 N5 1.372(3) . ?
N6 N7 1.322(3) . ?
N7 N8 1.303(3) . ?
N7 H7 0.8600 . ?
N8 N9 1.345(4) . ?
O1 S1 1.531(2) . ?

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 C1 N5 109.6(2) . . ?
N2 C1 N1 128.8(3) . . ?
N5 C1 N1 121.6(3) . . ?
N6 C2 N9 114.5(3) . . ?
N6 C2 N5 124.5(2) . . ?
N9 C2 N5 121.0(2) . . ?
S1 C3 H3A 109.5 . . ?
S1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
S1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
S1 C4 H4A 109.5 . . ?
S1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 N1 C1 122.9(3) 2_657 . ?
C1 N1 H1 118.53(16) 2_657 . ?
C1 N1 H1 118.53(17) . . ?
C1 N2 N3 105.0(2) . . ?
N4 N3 N2 111.9(2) . . ?
N3 N4 N5 106.1(2) . . ?
C1 N5 N4 107.3(2) . . ?
C1 N5 C2 130.3(2) . . ?
N4 N5 C2 122.3(2) . . ?
C2 N6 N7 100.6(2) . . ?
N8 N7 N6 114.8(2) . . ?
N8 N7 H7 122.6 . . ?
N6 N7 H7 122.6 . . ?
N7 N8 N9 105.8(2) . . ?
C2 N9 N8 104.3(2) . . ?
O1 S1 C4 104.74(15) . . ?
O1 S1 C3 103.70(15) . . ?
C4 S1 C3 98.53(16) . . ?

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
N2 C1 N1 C1 2.0(2) . . . 2_657 ?
N5 C1 N1 C1 -177.8(3) . . . 2_657 ?
N5 C1 N2 N3 -0.6(3) . . . . ?
N1 C1 N2 N3 179.7(3) . . . . ?
C1 N2 N3 N4 0.4(4) . . . . ?
N2 N3 N4 N5 -0.1(4) . . . . ?
N2 C1 N5 N4 0.5(3) . . . . ?
N1 C1 N5 N4 -179.7(2) . . . . ?
N2 C1 N5 C2 178.0(3) . . . . ?
N1 C1 N5 C2 -2.2(5) . . . . ?
N3 N4 N5 C1 -0.2(3) . . . . ?
N3 N4 N5 C2 -178.0(3) . . . . ?
N6 C2 N5 C1 -175.2(3) . . . . ?
N9 C2 N5 C1 5.8(6) . . . . ?
N6 C2 N5 N4 2.0(5) . . . . ?
N9 C2 N5 N4 -177.0(3) . . . . ?
N9 C2 N6 N7 -0.5(3) . . . . ?
N5 C2 N6 N7 -179.6(3) . . . . ?
C2 N6 N7 N8 0.0(3) . . . . ?
N6 N7 N8 N9 0.6(4) . . . . ?
N6 C2 N9 N8 0.9(4) . . . . ?
N5 C2 N9 N8 -180.0(3) . . . . ?
N7 N8 N9 C2 -0.8(3) . . . . ?

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
N7 H7 S1 0.86 2.77 3.582(3) 158.8 2_656 yes
N7 H7 O1 0.86 1.70 2.557(3) 171.7 2_656 yes
N1 H1 N9 0.78(6) 2.22(4) 2.806(4) 132.1(12) 2_657 yes
N1 H1 N9 0.78(6) 2.22(4) 2.806(4) 132.1(12) . yes

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_B_a
_audit_block_doi                 10.5517/ccdc.csd.cc26v137
_database_code_depnum_ccdc_archive 'CCDC 2050808'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00674F 2021
loop_
_audit_author_name
_audit_author_address
'YiFei Liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 N17, 3(H5 N2), H2 O'
_chemical_formula_sum            'C4 H17 N23 O'
_chemical_formula_weight         403.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4436(3)
_cell_length_b                   10.1464(5)
_cell_length_c                   11.1808(4)
_cell_angle_alpha                89.5300(10)
_cell_angle_beta                 74.8050(10)
_cell_angle_gamma                86.082(2)
_cell_volume                     812.97(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6397
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_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            12647
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3699
_reflns_number_gt                2849
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.2850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.081(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3699
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.49414(19) 0.82755(14) 0.52062(13) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.31207(19) 0.83985(14) 0.74588(13) 0.0229(3) Uani 1 1 d . . . . .
C3 C 0.79933(19) 0.75367(14) 0.43976(13) 0.0237(3) Uani 1 1 d . . . . .
C4 C 1.02621(19) 0.64529(14) 0.55015(13) 0.0244(3) Uani 1 1 d . . . . .
N1 N 0.65218(16) 0.76843(12) 0.53836(11) 0.0259(3) Uani 1 1 d . . . . .
N2 N 0.44670(17) 0.86558(13) 0.41758(11) 0.0280(3) Uani 1 1 d . . . . .
N3 N 0.26730(17) 0.91787(13) 0.45534(12) 0.0291(3) Uani 1 1 d . . . . .
N4 N 0.20179(16) 0.91511(12) 0.57323(11) 0.0266(3) Uani 1 1 d . . . . .
N5 N 0.34276(16) 0.85894(12) 0.61777(11) 0.0229(3) Uani 1 1 d . . . . .
N6 N 0.14404(19) 0.85772(17) 0.82191(12) 0.0404(4) Uani 1 1 d . . . . .
N7 N 0.1713(2) 0.82635(18) 0.93359(13) 0.0468(4) Uani 1 1 d . . . . .
N8 N 0.3467(2) 0.79205(16) 0.92166(12) 0.0415(4) Uani 1 1 d . . . . .
N9 N 0.44208(18) 0.80031(15) 0.80091(12) 0.0346(3) Uani 1 1 d . . . . .
N10 N 0.82342(18) 0.78651(13) 0.32063(11) 0.0312(3) Uani 1 1 d . . . . .
N11 N 1.00395(19) 0.74990(15) 0.26173(12) 0.0362(3) Uani 1 1 d . . . . .
N12 N 1.09276(18) 0.69669(14) 0.33548(12) 0.0333(3) Uani 1 1 d . . . . .
N13 N 0.96753(16) 0.69749(12) 0.44936(11) 0.0254(3) Uani 1 1 d . . . . .
N14 N 1.19937(17) 0.59541(13) 0.53578(12) 0.0312(3) Uani 1 1 d . . . . .
N15 N 1.20011(19) 0.55589(14) 0.65102(13) 0.0353(3) Uani 1 1 d . . . . .
N16 N 1.03608(19) 0.58181(14) 0.72705(13) 0.0363(3) Uani 1 1 d . . . . .
N17 N 0.91933(18) 0.63969(14) 0.66487(12) 0.0325(3) Uani 1 1 d . . . . .
N18 N 0.79931(17) 0.92607(13) 0.75200(11) 0.0304(3) Uani 1 1 d . . . . .
H18A H 0.812207 0.969067 0.673694 0.046 Uiso 1 1 d R U . . .
H18B H 0.716966 0.856004 0.758444 0.046 Uiso 1 1 d R U . . .
H18C H 0.919379 0.890234 0.757942 0.046 Uiso 1 1 d R U . . .
N19 N 0.72319(19) 1.02078(14) 0.85045(12) 0.0360(3) Uani 1 1 d . . . . .
H19A H 0.725308 0.972591 0.912585 0.054 Uiso 1 1 d R U . . .
H19B H 0.826665 1.076656 0.847693 0.054 Uiso 1 1 d R U . . .
N20 N 0.55793(18) 0.51748(14) 0.69452(12) 0.0318(3) Uani 1 1 d . . . . .
H20A H 0.440384 0.540726 0.676890 0.048 Uiso 1 1 d R U . . .
H20B H 0.626393 0.450916 0.636651 0.048 Uiso 1 1 d R U . . .
H20C H 0.628394 0.594287 0.687271 0.048 Uiso 1 1 d R U . . .
N21 N 0.5265(2) 0.46782(15) 0.81787(13) 0.0440(4) Uani 1 1 d . . . . .
H21A H 0.630619 0.470651 0.842426 0.066 Uiso 1 1 d R U . . .
H21B H 0.435374 0.517872 0.868223 0.066 Uiso 1 1 d R U . . .
N22 N 0.7445(2) 0.80480(18) 0.04204(14) 0.0518(4) Uani 1 1 d . . . . .
H22A H 0.847244 0.828182 0.060494 0.078 Uiso 1 1 d R U . . .
H22B H 0.765876 0.724927 0.006811 0.078 Uiso 1 1 d R U . . .
N23 N 0.5974(2) 0.80045(15) 0.15383(12) 0.0382(3) Uani 1 1 d . . . . .
H23A H 0.640777 0.817121 0.218736 0.057 Uiso 1 1 d R U . . .
H23B H 0.552381 0.720877 0.161640 0.057 Uiso 1 1 d R U . . .
H23C H 0.506909 0.861225 0.150280 0.057 Uiso 1 1 d R U . . .
O1 O 0.8172(2) 0.48413(19) 0.95573(14) 0.0745(5) Uani 1 1 d . . . . .
H1B H 0.919374 0.504210 0.897825 0.112 Uiso 1 1 d R U . . .
H1A H 0.861558 0.408379 0.978890 0.112 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.3372(18) . ?
C1 N1 1.3442(18) . ?
C1 N5 1.3660(18) . ?
C2 N9 1.3157(19) . ?
C2 N6 1.3169(19) . ?
C2 N5 1.4040(18) . ?
C3 N1 1.3360(18) . ?
C3 N10 1.3390(19) . ?
C3 N13 1.3696(18) . ?
C4 N14 1.3217(19) . ?
C4 N17 1.3234(19) . ?
C4 N13 1.3993(19) . ?
N2 N3 1.3617(17) . ?
N3 N4 1.2808(17) . ?
N4 N5 1.3644(16) . ?
N6 N7 1.349(2) . ?
N7 N8 1.301(2) . ?
N8 N9 1.3556(18) . ?
N10 N11 1.3599(18) . ?
N11 N12 1.2799(19) . ?
N12 N13 1.3665(17) . ?
N14 N15 1.3476(19) . ?
N15 N16 1.303(2) . ?
N16 N17 1.3504(18) . ?
N18 N19 1.4396(18) . ?
N18 H18A 0.9600 . ?
N18 H18B 0.9601 . ?
N18 H18C 0.9601 . ?
N19 H19A 0.8491 . ?
N19 H19B 0.9811 . ?
N20 N21 1.4304(19) . ?
N20 H20A 0.9600 . ?
N20 H20B 0.9601 . ?
N20 H20C 0.9600 . ?
N21 H21A 0.8900 . ?
N21 H21B 0.8900 . ?
N22 N23 1.4323(19) . ?
N22 H22A 0.8900 . ?
N22 H22B 0.8900 . ?
N23 H23A 0.8900 . ?
N23 H23B 0.8900 . ?
N23 H23C 0.8900 . ?
O1 H1B 0.8946 . ?
O1 H1A 0.8797 . ?

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 C1 N1 131.76(13) . . ?
N2 C1 N5 106.80(12) . . ?
N1 C1 N5 121.44(12) . . ?
N9 C2 N6 113.89(13) . . ?
N9 C2 N5 124.72(13) . . ?
N6 C2 N5 121.37(13) . . ?
N1 C3 N10 132.23(13) . . ?
N1 C3 N13 121.53(13) . . ?
N10 C3 N13 106.22(12) . . ?
N14 C4 N17 114.26(14) . . ?
N14 C4 N13 120.78(13) . . ?
N17 C4 N13 124.95(13) . . ?
C3 N1 C1 117.35(12) . . ?
C1 N2 N3 106.01(12) . . ?
N4 N3 N2 112.52(12) . . ?
N3 N4 N5 105.61(11) . . ?
N4 N5 C1 109.05(11) . . ?
N4 N5 C2 119.23(11) . . ?
C1 N5 C2 131.69(12) . . ?
C2 N6 N7 103.53(13) . . ?
N8 N7 N6 109.75(13) . . ?
N7 N8 N9 109.38(13) . . ?
C2 N9 N8 103.44(12) . . ?
C3 N10 N11 106.68(12) . . ?
N12 N11 N10 112.15(12) . . ?
N11 N12 N13 105.85(12) . . ?
N12 N13 C3 109.10(12) . . ?
N12 N13 C4 118.84(12) . . ?
C3 N13 C4 132.06(12) . . ?
C4 N14 N15 102.90(13) . . ?
N16 N15 N14 110.17(12) . . ?
N15 N16 N17 109.64(13) . . ?
C4 N17 N16 103.03(12) . . ?
N19 N18 H18A 109.2 . . ?
N19 N18 H18B 109.6 . . ?
H18A N18 H18B 109.5 . . ?
N19 N18 H18C 109.6 . . ?
H18A N18 H18C 109.5 . . ?
H18B N18 H18C 109.5 . . ?
N18 N19 H19A 99.8 . . ?
N18 N19 H19B 103.7 . . ?
H19A N19 H19B 101.6 . . ?
N21 N20 H20A 109.6 . . ?
N21 N20 H20B 109.5 . . ?
H20A N20 H20B 109.5 . . ?
N21 N20 H20C 109.3 . . ?
H20A N20 H20C 109.5 . . ?
H20B N20 H20C 109.5 . . ?
N20 N21 H21A 109.2 . . ?
N20 N21 H21B 109.2 . . ?
H21A N21 H21B 109.5 . . ?
N23 N22 H22A 109.1 . . ?
N23 N22 H22B 108.9 . . ?
H22A N22 H22B 109.5 . . ?
N22 N23 H23A 109.8 . . ?
N22 N23 H23B 109.7 . . ?
H23A N23 H23B 109.5 . . ?
N22 N23 H23C 108.9 . . ?
H23A N23 H23C 109.5 . . ?
H23B N23 H23C 109.5 . . ?
H1B O1 H1A 97.9 . . ?

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 C3 N1 C1 -0.4(2) . . . . ?
N13 C3 N1 C1 178.41(13) . . . . ?
N2 C1 N1 C3 7.4(2) . . . . ?
N5 C1 N1 C3 -173.28(13) . . . . ?
N1 C1 N2 N3 178.85(15) . . . . ?
N5 C1 N2 N3 -0.51(15) . . . . ?
C1 N2 N3 N4 0.19(16) . . . . ?
N2 N3 N4 N5 0.21(16) . . . . ?
N3 N4 N5 C1 -0.53(15) . . . . ?
N3 N4 N5 C2 -178.85(12) . . . . ?
N2 C1 N5 N4 0.66(15) . . . . ?
N1 C1 N5 N4 -178.79(12) . . . . ?
N2 C1 N5 C2 178.69(14) . . . . ?
N1 C1 N5 C2 -0.8(2) . . . . ?
N9 C2 N5 N4 -172.26(13) . . . . ?
N6 C2 N5 N4 9.5(2) . . . . ?
N9 C2 N5 C1 9.9(2) . . . . ?
N6 C2 N5 C1 -168.32(15) . . . . ?
N9 C2 N6 N7 -0.20(19) . . . . ?
N5 C2 N6 N7 178.18(14) . . . . ?
C2 N6 N7 N8 -0.1(2) . . . . ?
N6 N7 N8 N9 0.3(2) . . . . ?
N6 C2 N9 N8 0.37(19) . . . . ?
N5 C2 N9 N8 -177.95(14) . . . . ?
N7 N8 N9 C2 -0.39(19) . . . . ?
N1 C3 N10 N11 178.87(15) . . . . ?
N13 C3 N10 N11 -0.09(16) . . . . ?
C3 N10 N11 N12 0.17(18) . . . . ?
N10 N11 N12 N13 -0.18(17) . . . . ?
N11 N12 N13 C3 0.12(16) . . . . ?
N11 N12 N13 C4 -179.69(12) . . . . ?
N1 C3 N13 N12 -179.11(13) . . . . ?
N10 C3 N13 N12 -0.02(16) . . . . ?
N1 C3 N13 C4 0.7(2) . . . . ?
N10 C3 N13 C4 179.76(14) . . . . ?
N14 C4 N13 N12 -0.3(2) . . . . ?
N17 C4 N13 N12 -179.80(14) . . . . ?
N14 C4 N13 C3 179.92(14) . . . . ?
N17 C4 N13 C3 0.4(2) . . . . ?
N17 C4 N14 N15 -0.14(17) . . . . ?
N13 C4 N14 N15 -179.68(12) . . . . ?
C4 N14 N15 N16 0.03(16) . . . . ?
N14 N15 N16 N17 0.09(17) . . . . ?
N14 C4 N17 N16 0.19(17) . . . . ?
N13 C4 N17 N16 179.70(13) . . . . ?
N15 N16 N17 C4 -0.16(17) . . . . ?

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
N18 H18A N3 0.96 2.02 2.9261(18) 156.9 2_676 yes
N18 H18B N9 0.96 2.09 2.9475(19) 147.6 . yes
N18 H18C N4 0.96 2.56 3.1308(17) 118.5 1_655 yes
N18 H18C N6 0.96 1.99 2.9113(19) 159.9 1_655 yes
N19 H19A N22 0.85 2.25 3.077(2) 165.9 1_556 yes
N19 H19B N7 0.98 2.65 3.174(2) 113.9 2_677 yes
N19 H19B N11 0.98 2.38 3.221(2) 144.0 2_776 yes
N20 H20A N15 0.96 1.88 2.8314(19) 169.9 1_455 yes
N20 H20B N12 0.96 2.57 3.2214(18) 125.1 2_766 yes
N20 H20B N14 0.96 2.06 2.9211(18) 148.5 2_766 yes
N20 H20C N1 0.96 2.40 3.0909(18) 128.4 . yes
N20 H20C N9 0.96 2.58 3.094(2) 114.1 . yes
N20 H20C N17 0.96 2.19 2.9775(19) 138.0 . yes
N21 H21A O1 0.89 2.12 2.981(2) 162.0 . yes
N21 H21B O1 0.89 2.34 3.105(2) 144.2 2_667 yes
N22 H22A N7 0.89 2.46 3.111(2) 130.8 1_654 yes
N22 H22B O1 0.89 2.49 3.369(3) 167.4 1_554 yes
N23 H23A N2 0.89 2.35 2.9305(18) 123.2 . yes
N23 H23A N10 0.89 2.00 2.8174(19) 152.5 . yes
N23 H23B N21 0.89 2.03 2.921(2) 174.5 2_666 yes
N23 H23C N19 0.89 2.02 2.907(2) 172.0 2_676 yes
O1 H1B N16 0.89 2.05 2.858(2) 149.0 . yes
O1 H1A N7 0.88 2.57 3.379(3) 153.3 2_667 yes
O1 H1A N8 0.88 2.70 3.278(3) 124.8 2_667 yes

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045

