# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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 
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data_mo_20731099543_cs_0m
_database_code_depnum_ccdc_archive 'CCDC 2376608'
loop_
_audit_author_name
_audit_author_address
'Guofeng Zhang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-08-09 deposited with the CCDC.	2024-12-05 downloaded from the CCDC.
;
_audit_creation_date             2024-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 Cs N12'
_chemical_formula_sum            'C4 H3 Cs N12'
_chemical_formula_weight         352.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.3680 2.1192 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6704(2)
_cell_length_b                   8.0941(3)
_cell_length_c                   8.4392(3)
_cell_angle_alpha                90.8660(10)
_cell_angle_beta                 109.2380(10)
_cell_angle_gamma                92.4870(10)
_cell_volume                     493.98(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6260
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.683
_shelx_estimated_absorpt_T_min   0.641
_exptl_absorpt_coefficient_mu    3.750
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.8626.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10547
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.321
_diffrn_reflns_theta_min         2.520
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1718
_reflns_number_total             1790
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0183
_refine_ls_R_factor_gt           0.0174
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0235P)²+0.2810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0434
_refine_ls_wR_factor_ref         0.0438
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cs1 Cs 0.85655(2) -0.19575(2) 0.78024(2) 0.03152(8) Uani 1 1 d . . . . .
N1 N 0.7089(3) 0.1979(3) 0.8949(3) 0.0400(6) Uani 1 1 d . . . . .
C1 C 0.6440(4) 0.3460(3) 0.8821(3) 0.0325(6) Uani 1 1 d . . . . .
H1 H 0.680975 0.430520 0.965703 0.039 Uiso 1 1 calc R U . . .
N2 N 0.6159(3) 0.1174(3) 0.7448(3) 0.0409(6) Uani 1 1 d . . . . .
C2 C 0.4040(3) 0.4883(3) 0.6629(3) 0.0237(5) Uani 1 1 d . . . . .
N3 N 0.5002(3) 0.2114(3) 0.6446(3) 0.0357(5) Uani 1 1 d . . . . .
C3 C 0.2926(3) 0.7190(3) 0.6496(3) 0.0235(5) Uani 1 1 d . . . . .
N4 N 0.5164(3) 0.3569(2) 0.7305(3) 0.0247(4) Uani 1 1 d . . . . .
C4 C 0.0575(3) 0.6707(3) 0.3658(3) 0.0231(5) Uani 1 1 d . . . . .
N5 N 0.2762(3) 0.4732(2) 0.5155(3) 0.0249(4) Uani 1 1 d . . . . .
N6 N 0.4263(3) 0.6324(3) 0.7522(3) 0.0259(4) Uani 1 1 d . . . . .
N7 N 0.2022(3) 0.6282(2) 0.5076(2) 0.0240(4) Uani 1 1 d . . . . .
N8 N -0.0200(3) 0.5673(3) 0.2371(3) 0.0284(5) Uani 1 1 d . . . . .
N9 N -0.1482(3) 0.6595(3) 0.1306(3) 0.0331(5) Uani 1 1 d . . . . .
N10 N -0.1433(3) 0.8077(3) 0.1960(3) 0.0355(5) Uani 1 1 d . . . . .
N11 N -0.0107(3) 0.8200(3) 0.3499(3) 0.0312(5) Uani 1 1 d . . . . .
N12 N 0.2456(3) 0.8696(3) 0.6819(3) 0.0330(5) Uani 1 1 d . . . . .
H12A H 0.224396 0.932817 0.591271 0.040 Uiso 1 1 calc R U . . .
H12B H 0.335755 0.920033 0.768278 0.040 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
Cs1 Cs1 4.7226(3) 2_757 ?
Cs1 N1 3.552(2) 2_757 ?
Cs1 N2 3.160(2) . ?
Cs1 N3 3.721(2) 2_656 ?
Cs1 N5 3.204(2) 2_656 ?
Cs1 N6 3.458(2) 1_545 ?
Cs1 N8 3.328(2) 2_656 ?
Cs1 N9 3.208(2) 1_646 ?
Cs1 N10 3.508(2) 1_646 ?
Cs1 N10 3.720(2) 2_666 ?
Cs1 N11 3.535(2) 2_666 ?
Cs1 N12 3.374(2) 1_645 ?
N1 C1 1.310(4) . ?
N1 N2 1.370(4) . ?
C1 H1 0.9400 . ?
C1 N4 1.337(3) . ?
N2 N3 1.291(3) . ?
C2 N4 1.405(3) . ?
C2 N5 1.306(3) . ?
C2 N6 1.352(3) . ?
N3 N4 1.353(3) . ?
C3 N6 1.337(3) . ?
C3 N7 1.356(3) . ?
C3 N12 1.336(3) . ?
C4 N7 1.397(3) . ?
C4 N8 1.318(3) . ?
C4 N11 1.329(3) . ?
N5 N7 1.393(3) . ?
N8 N9 1.354(3) . ?
N9 N10 1.307(3) . ?
N10 N11 1.360(3) . ?
N12 H12A 0.9000 . ?
N12 H12B 0.9000 . ?

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 Cs1 Cs1 49.91(4) 2_757 2_757 ?
N1 Cs1 N3 161.30(6) 2_757 2_656 ?
N1 Cs1 N10 67.58(5) 2_757 2_666 ?
N2 Cs1 Cs1 69.54(5) . 2_757 ?
N2 Cs1 N1 119.31(6) . 2_757 ?
N2 Cs1 N3 71.25(6) . 2_656 ?
N2 Cs1 N5 117.45(6) . 2_656 ?
N2 Cs1 N6 77.19(6) . 1_545 ?
N2 Cs1 N8 166.99(6) . 2_656 ?
N2 Cs1 N9 102.55(7) . 1_646 ?
N2 Cs1 N10 84.72(6) . 1_646 ?
N2 Cs1 N10 69.08(6) . 2_666 ?
N2 Cs1 N11 60.66(6) . 2_666 ?
N2 Cs1 N12 114.26(6) . 1_645 ?
N3 Cs1 Cs1 138.73(3) 2_656 2_757 ?
N5 Cs1 Cs1 171.37(4) 2_656 2_757 ?
N5 Cs1 N1 122.54(5) 2_656 2_757 ?
N5 Cs1 N3 46.78(5) 2_656 2_656 ?
N5 Cs1 N6 69.74(5) 2_656 1_545 ?
N5 Cs1 N8 51.10(5) 2_656 2_656 ?
N5 Cs1 N9 111.38(5) 2_656 1_646 ?
N5 Cs1 N10 131.99(5) 2_656 1_646 ?
N5 Cs1 N10 128.63(5) 2_656 2_666 ?
N5 Cs1 N11 112.65(5) 2_656 2_666 ?
N5 Cs1 N12 88.28(5) 2_656 1_645 ?
N6 Cs1 Cs1 117.99(3) 1_545 2_757 ?
N6 Cs1 N1 131.43(5) 1_545 2_757 ?
N6 Cs1 N3 63.80(5) 1_545 2_656 ?
N6 Cs1 N10 146.19(5) 1_545 2_666 ?
N6 Cs1 N10 75.57(5) 1_545 1_646 ?
N6 Cs1 N11 133.91(5) 1_545 2_666 ?
N8 Cs1 Cs1 122.52(4) 2_656 2_757 ?
N8 Cs1 N1 73.19(6) 2_656 2_757 ?
N8 Cs1 N3 97.85(5) 2_656 2_656 ?
N8 Cs1 N6 91.75(5) 2_656 1_545 ?
N8 Cs1 N10 99.30(5) 2_656 1_646 ?
N8 Cs1 N10 122.02(5) 2_656 2_666 ?
N8 Cs1 N11 126.80(5) 2_656 2_666 ?
N8 Cs1 N12 74.07(5) 2_656 1_645 ?
N9 Cs1 Cs1 70.27(4) 1_646 2_757 ?
N9 Cs1 N1 63.91(6) 1_646 2_757 ?
N9 Cs1 N3 131.61(6) 1_646 2_656 ?
N9 Cs1 N6 68.02(5) 1_646 1_545 ?
N9 Cs1 N8 79.12(5) 1_646 2_656 ?
N9 Cs1 N10 21.86(6) 1_646 1_646 ?
N9 Cs1 N10 116.53(6) 1_646 2_666 ?
N9 Cs1 N11 135.67(5) 1_646 2_666 ?
N9 Cs1 N12 123.58(6) 1_646 1_645 ?
N10 Cs1 Cs1 47.28(4) 2_666 2_757 ?
N10 Cs1 Cs1 51.17(4) 1_646 2_757 ?
N10 Cs1 N1 62.44(6) 1_646 2_757 ?
N10 Cs1 N3 136.12(5) 1_646 2_656 ?
N10 Cs1 N3 105.94(5) 2_666 2_656 ?
N10 Cs1 N10 98.46(5) 1_646 2_666 ?
N10 Cs1 N11 115.29(5) 1_646 2_666 ?
N11 Cs1 Cs1 65.42(4) 2_666 2_757 ?
N11 Cs1 N1 87.95(5) 2_666 2_757 ?
N11 Cs1 N3 84.52(5) 2_666 2_656 ?
N11 Cs1 N10 21.42(5) 2_666 2_666 ?
N12 Cs1 Cs1 83.98(4) 1_645 2_757 ?
N12 Cs1 N1 61.15(6) 1_645 2_757 ?
N12 Cs1 N3 100.90(6) 1_645 2_656 ?
N12 Cs1 N6 158.01(5) 1_645 1_545 ?
N12 Cs1 N10 122.59(6) 1_645 1_646 ?
N12 Cs1 N10 50.13(5) 1_645 2_666 ?
N12 Cs1 N11 53.60(5) 1_645 2_666 ?
C1 N1 Cs1 110.52(18) . 2_757 ?
C1 N1 N2 105.4(2) . . ?
N2 N1 Cs1 139.18(17) . 2_757 ?
N1 C1 H1 125.6 . . ?
N1 C1 N4 108.8(2) . . ?
N4 C1 H1 125.6 . . ?
N1 N2 Cs1 99.65(15) . . ?
N3 N2 Cs1 146.82(19) . . ?
N3 N2 N1 111.3(2) . . ?
N5 C2 N4 121.1(2) . . ?
N5 C2 N6 119.2(2) . . ?
N6 C2 N4 119.8(2) . . ?
N2 N3 Cs1 139.99(17) . 2_656 ?
N2 N3 N4 105.5(2) . . ?
N4 N3 Cs1 114.43(14) . 2_656 ?
N6 C3 N7 110.1(2) . . ?
N12 C3 N6 126.2(2) . . ?
N12 C3 N7 123.6(2) . . ?
C1 N4 C2 129.3(2) . . ?
C1 N4 N3 108.9(2) . . ?
N3 N4 C2 121.7(2) . . ?
N8 C4 N7 122.9(2) . . ?
N8 C4 N11 114.9(2) . . ?
N11 C4 N7 122.2(2) . . ?
C2 N5 Cs1 135.94(15) . 2_656 ?
C2 N5 N7 99.66(19) . . ?
N7 N5 Cs1 124.34(14) . 2_656 ?
C2 N6 Cs1 106.58(14) . 1_565 ?
C3 N6 Cs1 110.44(15) . 1_565 ?
C3 N6 C2 101.05(19) . . ?
C3 N7 C4 129.6(2) . . ?
C3 N7 N5 110.01(19) . . ?
N5 N7 C4 120.4(2) . . ?
C4 N8 Cs1 121.11(15) . 2_656 ?
C4 N8 N9 102.8(2) . . ?
N9 N8 Cs1 135.78(15) . 2_656 ?
N8 N9 Cs1 127.55(16) . 1_464 ?
N10 N9 Cs1 92.12(15) . 1_464 ?
N10 N9 N8 110.2(2) . . ?
Cs1 N10 Cs1 81.54(5) 1_464 2_666 ?
N9 N10 Cs1 66.03(14) . 1_464 ?
N9 N10 Cs1 134.54(18) . 2_666 ?
N9 N10 N11 109.6(2) . . ?
N11 N10 Cs1 71.64(13) . 2_666 ?
N11 N10 Cs1 135.08(16) . 1_464 ?
C4 N11 Cs1 131.31(17) . 2_666 ?
C4 N11 N10 102.5(2) . . ?
N10 N11 Cs1 86.95(14) . 2_666 ?
Cs1 N12 H12A 110.8 1_465 . ?
Cs1 N12 H12B 110.8 1_465 . ?
C3 N12 Cs1 104.91(16) . 1_465 ?
C3 N12 H12A 110.8 . . ?
C3 N12 H12B 110.8 . . ?
H12A N12 H12B 108.8 . . ?

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
Cs1 N1 C1 N4 160.26(16) 2_757 . . . ?
Cs1 N1 N2 Cs1 17.0(3) 2_757 . . . ?
Cs1 N1 N2 N3 -151.0(2) 2_757 . . . ?
Cs1 N2 N3 Cs1 24.7(5) . . . 2_656 ?
Cs1 N2 N3 N4 -158.1(3) . . . . ?
Cs1 N3 N4 C1 178.16(16) 2_656 . . . ?
Cs1 N3 N4 C2 1.0(3) 2_656 . . . ?
Cs1 N5 N7 C3 -177.61(14) 2_656 . . . ?
Cs1 N5 N7 C4 1.5(3) 2_656 . . . ?
Cs1 N8 N9 Cs1 -63.3(3) 2_656 . . 1_464 ?
Cs1 N8 N9 N10 -172.79(17) 2_656 . . . ?
Cs1 N9 N10 Cs1 -48.44(19) 1_464 . . 2_666 ?
Cs1 N9 N10 N11 -131.63(18) 1_464 . . . ?
Cs1 N10 N11 Cs1 56.47(19) 1_464 . . 2_666 ?
Cs1 N10 N11 C4 -131.71(18) 2_666 . . . ?
Cs1 N10 N11 C4 -75.2(3) 1_464 . . . ?
N1 C1 N4 C2 176.8(2) . . . . ?
N1 C1 N4 N3 0.0(3) . . . . ?
N1 N2 N3 Cs1 -177.38(19) . . . 2_656 ?
N1 N2 N3 N4 -0.2(3) . . . . ?
C1 N1 N2 Cs1 168.14(19) . . . . ?
C1 N1 N2 N3 0.2(3) . . . . ?
N2 N1 C1 N4 -0.1(3) . . . . ?
N2 N3 N4 C1 0.1(3) . . . . ?
N2 N3 N4 C2 -177.0(2) . . . . ?
C2 N5 N7 C3 0.1(3) . . . . ?
C2 N5 N7 C4 179.2(2) . . . . ?
N4 C2 N5 Cs1 -4.5(4) . . . 2_656 ?
N4 C2 N5 N7 178.3(2) . . . . ?
N4 C2 N6 Cs1 66.7(2) . . . 1_565 ?
N4 C2 N6 C3 -177.8(2) . . . . ?
C4 N8 N9 Cs1 109.5(2) . . . 1_464 ?
C4 N8 N9 N10 0.0(3) . . . . ?
N5 C2 N4 C1 -175.0(2) . . . . ?
N5 C2 N4 N3 1.5(4) . . . . ?
N5 C2 N6 Cs1 -114.0(2) . . . 1_565 ?
N5 C2 N6 C3 1.4(3) . . . . ?
N6 C2 N4 C1 4.3(4) . . . . ?
N6 C2 N4 N3 -179.2(2) . . . . ?
N6 C2 N5 Cs1 176.29(15) . . . 2_656 ?
N6 C2 N5 N7 -1.0(3) . . . . ?
N6 C3 N7 C4 -178.2(2) . . . . ?
N6 C3 N7 N5 0.8(3) . . . . ?
N6 C3 N12 Cs1 -102.5(2) . . . 1_465 ?
N7 C3 N6 Cs1 111.31(18) . . . 1_565 ?
N7 C3 N6 C2 -1.2(3) . . . . ?
N7 C3 N12 Cs1 74.0(3) . . . 1_465 ?
N7 C4 N8 Cs1 -4.9(3) . . . 2_656 ?
N7 C4 N8 N9 -179.0(2) . . . . ?
N7 C4 N11 Cs1 82.0(3) . . . 2_666 ?
N7 C4 N11 N10 179.0(2) . . . . ?
N8 C4 N7 C3 -178.6(2) . . . . ?
N8 C4 N7 N5 2.4(3) . . . . ?
N8 C4 N11 Cs1 -97.1(2) . . . 2_666 ?
N8 C4 N11 N10 -0.1(3) . . . . ?
N8 N9 N10 Cs1 83.1(3) . . . 2_666 ?
N8 N9 N10 Cs1 131.6(2) . . . 1_464 ?
N8 N9 N10 N11 -0.1(3) . . . . ?
N9 N10 N11 Cs1 131.8(2) . . . 2_666 ?
N9 N10 N11 C4 0.1(3) . . . . ?
N11 C4 N7 C3 2.4(4) . . . . ?
N11 C4 N7 N5 -176.6(2) . . . . ?
N11 C4 N8 Cs1 174.17(16) . . . 2_656 ?
N11 C4 N8 N9 0.0(3) . . . . ?
N12 C3 N6 Cs1 -71.8(3) . . . 1_565 ?
N12 C3 N6 C2 175.7(3) . . . . ?
N12 C3 N7 C4 4.7(4) . . . . ?
N12 C3 N7 N5 -176.2(2) . . . . ?

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

data_cu_20240816_wq_240812109087_0m
_database_code_depnum_ccdc_archive 'CCDC 2378833'
loop_
_audit_author_name
_audit_author_address
'Guofeng Zhang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2024-12-05 downloaded from the CCDC.
;
_audit_creation_date             2024-08-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H7 N12 Na O2'
_chemical_formula_sum            'C4 H7 N12 Na O2'
_chemical_formula_weight         278.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5111(4)
_cell_length_b                   6.5119(2)
_cell_length_c                   26.0556(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2122.78(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4748
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      68.243
_cell_measurement_theta_min      3.393
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    1.578
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0875 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.8936.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15454
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.392
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1631
_reflns_number_total             1927
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         1927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.6204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0926
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.b X=CH2 refined with riding coordinates:
 N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.76742(7) 0.61556(12) 0.26375(3) 0.0408(2) Uani 1 1 d . . . . .
O1 O 0.69594(11) 0.8514(2) 0.32456(5) 0.0318(3) Uani 1 1 d . . . . .
H1A H 0.632(2) 0.848(4) 0.3365(9) 0.050(7) Uiso 1 1 d . . . . .
H1B H 0.737(2) 0.846(4) 0.3492(11) 0.067(9) Uiso 1 1 d . . . . .
O2 O 0.64518(11) 0.3960(2) 0.22522(5) 0.0356(4) Uani 1 1 d . . . . .
H2A H 0.586(2) 0.404(4) 0.2333(9) 0.054(8) Uiso 1 1 d . . . . .
H2B H 0.648(2) 0.390(4) 0.1915(11) 0.062(8) Uiso 1 1 d . . . . .
N1 N 0.62999(12) 0.6022(3) 0.68707(6) 0.0398(4) Uani 1 1 d . . . . .
N2 N 0.53239(12) 0.6159(3) 0.70919(6) 0.0467(5) Uani 1 1 d . . . . .
N3 N 0.45887(13) 0.6509(3) 0.67540(5) 0.0435(5) Uani 1 1 d . . . . .
N4 N 0.50905(11) 0.6603(2) 0.62995(5) 0.0249(3) Uani 1 1 d . . . . .
N5 N 0.50018(10) 0.7223(2) 0.54102(5) 0.0232(3) Uani 1 1 d . . . . .
N6 N 0.34266(10) 0.7015(2) 0.58554(5) 0.0236(3) Uani 1 1 d . . . . .
N7 N 0.41284(10) 0.7502(2) 0.50865(5) 0.0218(3) Uani 1 1 d . . . . .
N8 N 0.22345(10) 0.7560(2) 0.51568(5) 0.0282(4) Uani 1 1 d . . . . .
H8A H 0.166986 0.744915 0.534971 0.034 Uiso 1 1 calc R U . . .
H8B H 0.216558 0.779325 0.482969 0.034 Uiso 1 1 calc R U . . .
N9 N 0.52052(11) 0.7927(2) 0.43340(5) 0.0246(3) Uani 1 1 d . . . . .
N10 N 0.49615(11) 0.8385(2) 0.38409(5) 0.0284(3) Uani 1 1 d . . . . .
N11 N 0.39260(11) 0.8606(2) 0.37953(5) 0.0298(4) Uani 1 1 d . . . . .
N12 N 0.34454(11) 0.8299(2) 0.42531(5) 0.0284(4) Uani 1 1 d . . . . .
C1 C 0.61354(14) 0.6311(3) 0.63789(7) 0.0325(4) Uani 1 1 d . . . . .
H1 H 0.666612 0.631365 0.612355 0.039 Uiso 1 1 calc R U . . .
C2 C 0.45030(13) 0.6962(3) 0.58439(6) 0.0214(4) Uani 1 1 d . . . . .
C3 C 0.31991(12) 0.7373(3) 0.53611(6) 0.0217(4) Uani 1 1 d . . . . .
C4 C 0.42646(12) 0.7901(3) 0.45641(6) 0.0213(4) 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
Na1 Na1 3.2850(2) 7_755 ?
Na1 Na1 3.2850(2) 7_765 ?
Na1 O1 2.3810(15) . ?
Na1 O1 2.3828(15) 7_755 ?
Na1 O2 2.3533(16) 7_765 ?
Na1 O2 2.3219(16) . ?
Na1 N1 2.7657(17) 2_664 ?
O1 H1A 0.86(3) . ?
O1 H1B 0.82(3) . ?
O2 H2A 0.78(3) . ?
O2 H2B 0.88(3) . ?
N1 N2 1.353(2) . ?
N1 C1 1.312(2) . ?
N2 N3 1.294(2) . ?
N3 N4 1.3417(19) . ?
N4 C1 1.337(2) . ?
N4 C2 1.4156(19) . ?
N5 N7 1.3922(17) . ?
N5 C2 1.302(2) . ?
N6 C2 1.347(2) . ?
N6 C3 1.339(2) . ?
N7 C3 1.3677(19) . ?
N7 C4 1.3962(19) . ?
N8 H8A 0.8700 . ?
N8 H8B 0.8700 . ?
N8 C3 1.325(2) . ?
N9 N10 1.3537(18) . ?
N9 C4 1.321(2) . ?
N10 N11 1.309(2) . ?
N11 N12 1.3506(19) . ?
N12 C4 1.332(2) . ?
C1 H1 0.9400 . ?

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
Na1 Na1 Na1 164.75(6) 7_755 7_765 ?
O1 Na1 Na1 126.13(4) . 7_755 ?
O1 Na1 Na1 46.38(4) 7_755 7_755 ?
O1 Na1 Na1 137.81(4) 7_755 7_765 ?
O1 Na1 Na1 46.43(4) . 7_765 ?
O1 Na1 O1 95.48(6) . 7_755 ?
O1 Na1 N1 170.30(6) . 2_664 ?
O1 Na1 N1 91.20(6) 7_755 2_664 ?
O2 Na1 Na1 45.75(4) . 7_755 ?
O2 Na1 Na1 146.18(5) 7_765 7_755 ?
O2 Na1 Na1 44.97(4) 7_765 7_765 ?
O2 Na1 Na1 121.53(5) . 7_765 ?
O2 Na1 O1 138.96(6) 7_765 7_755 ?
O2 Na1 O1 88.26(5) . 7_755 ?
O2 Na1 O1 87.58(5) 7_765 . ?
O2 Na1 O1 115.95(6) . . ?
O2 Na1 O2 126.83(7) . 7_765 ?
O2 Na1 N1 82.76(5) 7_765 2_664 ?
O2 Na1 N1 71.20(5) . 2_664 ?
N1 Na1 Na1 63.48(4) 2_664 7_755 ?
N1 Na1 Na1 124.73(4) 2_664 7_765 ?
Na1 O1 Na1 87.19(5) . 7_765 ?
Na1 O1 H1A 124.9(16) . . ?
Na1 O1 H1A 116.1(16) 7_765 . ?
Na1 O1 H1B 105.0(19) . . ?
Na1 O1 H1B 115(2) 7_765 . ?
H1A O1 H1B 107(2) . . ?
Na1 O2 Na1 89.28(5) . 7_755 ?
Na1 O2 H2A 118.1(19) . . ?
Na1 O2 H2A 112.6(19) 7_755 . ?
Na1 O2 H2B 115.8(17) . . ?
Na1 O2 H2B 112.2(17) 7_755 . ?
H2A O2 H2B 108(2) . . ?
N2 N1 Na1 98.34(11) . 2_665 ?
C1 N1 Na1 148.47(14) . 2_665 ?
C1 N1 N2 105.37(14) . . ?
N3 N2 N1 111.32(14) . . ?
N2 N3 N4 106.02(14) . . ?
N3 N4 C2 120.31(13) . . ?
C1 N4 N3 108.33(14) . . ?
C1 N4 C2 131.36(14) . . ?
C2 N5 N7 99.59(12) . . ?
C3 N6 C2 101.27(13) . . ?
N5 N7 C4 121.27(12) . . ?
C3 N7 N5 110.02(12) . . ?
C3 N7 C4 128.69(13) . . ?
H8A N8 H8B 120.0 . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
C4 N9 N10 103.47(12) . . ?
N11 N10 N9 109.47(12) . . ?
N10 N11 N12 110.13(13) . . ?
C4 N12 N11 102.92(13) . . ?
N1 C1 N4 108.97(15) . . ?
N1 C1 H1 125.5 . . ?
N4 C1 H1 125.5 . . ?
N5 C2 N4 120.04(14) . . ?
N5 C2 N6 119.66(14) . . ?
N6 C2 N4 120.30(14) . . ?
N6 C3 N7 109.45(13) . . ?
N8 C3 N6 126.58(14) . . ?
N8 C3 N7 123.96(14) . . ?
N9 C4 N7 123.62(13) . . ?
N9 C4 N12 114.01(14) . . ?
N12 C4 N7 122.37(14) . . ?

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
Na1 N1 N2 N3 -158.79(16) 2_665 . . . ?
Na1 N1 C1 N4 136.9(2) 2_665 . . . ?
N1 N2 N3 N4 0.1(2) . . . . ?
N2 N1 C1 N4 -0.4(2) . . . . ?
N2 N3 N4 C1 -0.3(2) . . . . ?
N2 N3 N4 C2 179.68(17) . . . . ?
N3 N4 C1 N1 0.5(2) . . . . ?
N3 N4 C2 N5 174.26(17) . . . . ?
N3 N4 C2 N6 -6.4(3) . . . . ?
N5 N7 C3 N6 -0.11(19) . . . . ?
N5 N7 C3 N8 -179.46(16) . . . . ?
N5 N7 C4 N9 4.0(3) . . . . ?
N5 N7 C4 N12 -175.74(16) . . . . ?
N7 N5 C2 N4 179.69(15) . . . . ?
N7 N5 C2 N6 0.4(2) . . . . ?
N9 N10 N11 N12 -0.2(2) . . . . ?
N10 N9 C4 N7 -179.50(16) . . . . ?
N10 N9 C4 N12 0.3(2) . . . . ?
N10 N11 N12 C4 0.32(19) . . . . ?
N11 N12 C4 N7 179.42(16) . . . . ?
N11 N12 C4 N9 -0.4(2) . . . . ?
C1 N1 N2 N3 0.2(3) . . . . ?
C1 N4 C2 N5 -5.7(3) . . . . ?
C1 N4 C2 N6 173.57(19) . . . . ?
C2 N4 C1 N1 -179.53(18) . . . . ?
C2 N5 N7 C3 -0.14(18) . . . . ?
C2 N5 N7 C4 178.33(15) . . . . ?
C2 N6 C3 N7 0.31(18) . . . . ?
C2 N6 C3 N8 179.63(18) . . . . ?
C3 N6 C2 N4 -179.77(15) . . . . ?
C3 N6 C2 N5 -0.5(2) . . . . ?
C3 N7 C4 N9 -177.79(17) . . . . ?
C3 N7 C4 N12 2.4(3) . . . . ?
C4 N7 C3 N6 -178.44(16) . . . . ?
C4 N7 C3 N8 2.2(3) . . . . ?
C4 N9 N10 N11 -0.08(19) . . . . ?

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

data_cu_240822177350_0m
_database_code_depnum_ccdc_archive 'CCDC 2385568'
loop_
_audit_author_name
_audit_author_address
'Guofeng Zhang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-09-21 deposited with the CCDC.	2024-12-05 downloaded from the CCDC.
;
_audit_creation_date             2024-08-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H5 K N12 O'
_chemical_formula_sum            'C4 H5 K N12 O'
_chemical_formula_weight         276.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7583(2)
_cell_length_b                   7.8975(2)
_cell_length_c                   9.8534(3)
_cell_angle_alpha                85.648(2)
_cell_angle_beta                 73.651(2)
_cell_angle_gamma                87.923(2)
_cell_volume                     503.13(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3016
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      79.072
_cell_measurement_theta_min      4.688
_shelx_estimated_absorpt_T_max   0.619
_shelx_estimated_absorpt_T_min   0.573
_exptl_absorpt_coefficient_mu    4.827
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0915 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.8141.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6944
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.061
_diffrn_reflns_theta_min         4.688
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1748
_reflns_number_total             2084
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2084
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.2802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1105
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.c X=CH2 refined with riding coordinates:
 N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.84497(9) 0.05214(6) 0.27197(5) 0.03628(18) Uani 1 1 d . . . . .
O1 O 0.6249(3) 0.1418(2) 0.08435(18) 0.0388(4) Uani 1 1 d . . . . .
H1A H 0.690247 0.108646 0.001862 0.058 Uiso 1 1 d R U . . .
H1B H 0.511257 0.086004 0.107849 0.058 Uiso 1 1 d R U . . .
N1 N 0.7602(4) 0.1426(2) 0.5523(2) 0.0343(5) Uani 1 1 d . . . . .
C1 C 0.7371(3) 0.3014(3) 0.5897(2) 0.0245(4) Uani 1 1 d . . . . .
N2 N 0.7404(4) 0.0517(2) 0.6766(2) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.7522(3) 0.6106(3) 0.5129(2) 0.0236(4) Uani 1 1 d . . . . .
N3 N 0.7073(3) 0.1542(2) 0.7798(2) 0.0356(5) Uani 1 1 d . . . . .
C3 C 0.7722(3) 0.5784(3) 0.3013(2) 0.0244(4) Uani 1 1 d . . . . .
N4 N 0.7035(3) 0.3166(2) 0.7270(2) 0.0321(4) Uani 1 1 d . . . . .
C4 C 0.7332(4) 0.5276(3) 0.0637(2) 0.0303(5) Uani 1 1 d . . . . .
H4 H 0.672974 0.419754 0.083515 0.036 Uiso 1 1 calc R U . . .
N5 N 0.7463(3) 0.4418(2) 0.49258(18) 0.0246(4) Uani 1 1 d . . . . .
N6 N 0.7622(3) 0.4198(2) 0.35117(18) 0.0263(4) Uani 1 1 d . . . . .
N7 N 0.7677(3) 0.7014(2) 0.38994(19) 0.0251(4) Uani 1 1 d . . . . .
N8 N 0.7444(3) 0.6717(2) 0.6364(2) 0.0304(4) Uani 1 1 d . . . . .
H8A H 0.749285 0.780686 0.642493 0.037 Uiso 1 1 calc R U . . .
H8B H 0.734271 0.602691 0.711088 0.037 Uiso 1 1 calc R U . . .
N9 N 0.7875(3) 0.6180(2) 0.15715(18) 0.0249(4) Uani 1 1 d . . . . .
N10 N 0.8671(3) 0.7665(2) 0.0905(2) 0.0338(5) Uani 1 1 d . . . . .
N11 N 0.8603(4) 0.7622(3) -0.0392(2) 0.0370(5) Uani 1 1 d . . . . .
N12 N 0.7779(3) 0.6142(3) -0.0596(2) 0.0337(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O1 2.7212(18) . ?
K1 N1 2.801(2) . ?
K1 N2 3.058(2) 2_756 ?
K1 N3 3.312(2) 2_756 ?
K1 N6 3.0553(18) . ?
K1 N7 2.9276(18) 1_545 ?
K1 N10 2.957(2) 1_545 ?
K1 N11 2.916(2) 2_765 ?
O1 H1A 0.8638 . ?
O1 H1B 0.8638 . ?
N1 C1 1.325(3) . ?
N1 N2 1.347(3) . ?
C1 N4 1.322(3) . ?
C1 N5 1.400(3) . ?
N2 N3 1.313(3) . ?
C2 N5 1.367(3) . ?
C2 N7 1.340(3) . ?
C2 N8 1.329(3) . ?
N3 N4 1.349(3) . ?
C3 N6 1.307(3) . ?
C3 N7 1.348(3) . ?
C3 N9 1.407(3) . ?
C4 H4 0.9400 . ?
C4 N9 1.342(3) . ?
C4 N12 1.311(3) . ?
N5 N6 1.391(2) . ?
N8 H8A 0.8700 . ?
N8 H8B 0.8700 . ?
N9 N10 1.351(3) . ?
N10 N11 1.295(3) . ?
N11 N12 1.365(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 K1 N1 127.23(6) . . ?
O1 K1 N2 148.53(6) . 2_756 ?
O1 K1 N3 129.27(6) . 2_756 ?
O1 K1 N6 83.97(5) . . ?
O1 K1 N7 111.82(5) . 1_545 ?
O1 K1 N10 71.88(6) . 1_545 ?
O1 K1 N11 76.28(6) . 2_765 ?
N1 K1 N2 81.60(6) . 2_756 ?
N1 K1 N3 103.26(6) . 2_756 ?
N1 K1 N6 57.76(5) . . ?
N1 K1 N7 86.76(5) . 1_545 ?
N1 K1 N10 144.58(6) . 1_545 ?
N1 K1 N11 121.80(6) . 2_765 ?
N2 K1 N3 23.35(5) 2_756 2_756 ?
N6 K1 N2 106.43(5) . 2_756 ?
N6 K1 N3 125.91(6) . 2_756 ?
N7 K1 N2 78.43(5) 1_545 2_756 ?
N7 K1 N3 71.38(5) 1_545 2_756 ?
N7 K1 N6 142.00(5) 1_545 . ?
N7 K1 N10 57.84(5) 1_545 1_545 ?
N10 K1 N2 91.49(6) 1_545 2_756 ?
N10 K1 N3 68.76(6) 1_545 2_756 ?
N10 K1 N6 154.89(5) 1_545 . ?
N11 K1 N2 77.17(6) 2_765 2_756 ?
N11 K1 N3 72.91(6) 2_765 2_756 ?
N11 K1 N6 77.60(5) 2_765 . ?
N11 K1 N7 138.49(6) 2_765 1_545 ?
N11 K1 N10 89.80(6) 2_765 1_545 ?
K1 O1 H1A 109.6 . . ?
K1 O1 H1B 109.5 . . ?
H1A O1 H1B 104.4 . . ?
C1 N1 K1 124.00(14) . . ?
C1 N1 N2 102.98(18) . . ?
N2 N1 K1 132.99(14) . . ?
N1 C1 N5 123.10(19) . . ?
N4 C1 N1 114.39(19) . . ?
N4 C1 N5 122.51(19) . . ?
N1 N2 K1 112.96(16) . 2_756 ?
N3 N2 K1 89.26(15) . 2_756 ?
N3 N2 N1 109.88(18) . . ?
N7 C2 N5 109.25(18) . . ?
N8 C2 N5 124.35(19) . . ?
N8 C2 N7 126.40(19) . . ?
N2 N3 K1 67.40(13) . 2_756 ?
N2 N3 N4 109.66(18) . . ?
N4 N3 K1 119.27(15) . 2_756 ?
N6 C3 N7 119.00(19) . . ?
N6 C3 N9 119.78(19) . . ?
N7 C3 N9 121.22(18) . . ?
C1 N4 N3 103.10(18) . . ?
N9 C4 H4 125.6 . . ?
N12 C4 H4 125.6 . . ?
N12 C4 N9 108.8(2) . . ?
C2 N5 C1 129.08(18) . . ?
C2 N5 N6 110.14(16) . . ?
N6 N5 C1 120.70(17) . . ?
C3 N6 K1 144.62(14) . . ?
C3 N6 N5 99.87(16) . . ?
N5 N6 K1 113.73(11) . . ?
C2 N7 K1 138.62(14) . 1_565 ?
C2 N7 C3 101.72(17) . . ?
C3 N7 K1 118.95(13) . 1_565 ?
C2 N8 H8A 120.0 . . ?
C2 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C4 N9 C3 130.05(19) . . ?
C4 N9 N10 108.59(18) . . ?
N10 N9 C3 121.35(18) . . ?
N9 N10 K1 116.35(13) . 1_565 ?
N11 N10 K1 131.77(14) . 1_565 ?
N11 N10 N9 105.77(19) . . ?
N10 N11 K1 121.32(16) . 2_765 ?
N10 N11 N12 111.27(18) . . ?
N12 N11 K1 120.96(14) . 2_765 ?
C4 N12 N11 105.54(19) . . ?

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
K1 N1 C1 N4 -178.23(15) . . . . ?
K1 N1 C1 N5 2.1(3) . . . . ?
K1 N1 N2 K1 79.7(2) . . . 2_756 ?
K1 N1 N2 N3 177.69(17) . . . . ?
K1 N2 N3 N4 114.43(17) 2_756 . . . ?
K1 N3 N4 C1 74.1(2) 2_756 . . . ?
K1 N10 N11 K1 57.5(3) 1_565 . . 2_765 ?
K1 N10 N11 N12 -150.51(17) 1_565 . . . ?
K1 N11 N12 C4 152.43(16) 2_765 . . . ?
N1 C1 N4 N3 0.4(3) . . . . ?
N1 C1 N5 C2 -170.5(2) . . . . ?
N1 C1 N5 N6 5.9(3) . . . . ?
N1 N2 N3 K1 -114.2(2) . . . 2_756 ?
N1 N2 N3 N4 0.2(3) . . . . ?
C1 N1 N2 K1 -97.90(18) . . . 2_756 ?
C1 N1 N2 N3 0.0(3) . . . . ?
C1 N5 N6 K1 -9.5(2) . . . . ?
C1 N5 N6 C3 -178.15(19) . . . . ?
N2 N1 C1 N4 -0.3(3) . . . . ?
N2 N1 C1 N5 180.0(2) . . . . ?
N2 N3 N4 C1 -0.4(3) . . . . ?
C2 N5 N6 K1 167.51(13) . . . . ?
C2 N5 N6 C3 -1.1(2) . . . . ?
C3 N9 N10 K1 -24.6(2) . . . 1_565 ?
C3 N9 N10 N11 179.5(2) . . . . ?
N4 C1 N5 C2 9.8(4) . . . . ?
N4 C1 N5 N6 -173.8(2) . . . . ?
C4 N9 N10 K1 155.51(14) . . . 1_565 ?
C4 N9 N10 N11 -0.3(3) . . . . ?
N5 C1 N4 N3 -179.9(2) . . . . ?
N5 C2 N7 K1 -170.19(15) . . . 1_565 ?
N5 C2 N7 C3 -0.6(2) . . . . ?
N6 C3 N7 K1 171.97(15) . . . 1_565 ?
N6 C3 N7 C2 -0.2(3) . . . . ?
N6 C3 N9 C4 22.8(3) . . . . ?
N6 C3 N9 N10 -157.1(2) . . . . ?
N7 C2 N5 C1 177.8(2) . . . . ?
N7 C2 N5 N6 1.2(2) . . . . ?
N7 C3 N6 K1 -161.05(17) . . . . ?
N7 C3 N6 N5 0.8(3) . . . . ?
N7 C3 N9 C4 -157.2(2) . . . . ?
N7 C3 N9 N10 22.9(3) . . . . ?
N8 C2 N5 C1 -2.0(4) . . . . ?
N8 C2 N5 N6 -178.6(2) . . . . ?
N8 C2 N7 K1 9.6(4) . . . 1_565 ?
N8 C2 N7 C3 179.2(2) . . . . ?
N9 C3 N6 K1 18.9(4) . . . . ?
N9 C3 N6 N5 -179.17(19) . . . . ?
N9 C3 N7 K1 -8.0(3) . . . 1_565 ?
N9 C3 N7 C2 179.83(19) . . . . ?
N9 C4 N12 N11 -0.5(3) . . . . ?
N9 N10 N11 K1 -152.00(14) . . . 2_765 ?
N9 N10 N11 N12 0.0(3) . . . . ?
N10 N11 N12 C4 0.3(3) . . . . ?
N12 C4 N9 C3 -179.3(2) . . . . ?
N12 C4 N9 N10 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
