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

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

data_DZ200606_1_a
_database_code_depnum_ccdc_archive 'CCDC 2008382'
loop_
_audit_author_name
_audit_author_address
'Zhen Dong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-06-06 deposited with the CCDC.	2020-11-24 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 H2 N18'
_chemical_formula_sum            'C4 H2 N18'
_chemical_formula_weight         302.24

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.7578(10)
_cell_length_b                   7.7273(12)
_cell_length_c                   10.6046(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.283(5)
_cell_angle_gamma                90
_cell_volume                     552.86(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3037
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      27.45

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6835
_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 ?
_diffrn_reflns_number            5291
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.264
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1257
_reflns_number_gt                1069
_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)+(0.0489P)²+0.1476P] 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         1257
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0868
_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 0.23084(18) 0.77199(16) 0.27735(12) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.51732(17) 0.69896(16) 0.42696(11) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.19795(16) 0.81460(16) 0.15827(11) 0.0322(3) Uani 1 1 d . . . . .
N2 N 0.01215(17) 0.76480(16) 0.14087(11) 0.0344(3) Uani 1 1 d . . . . .
H2 H -0.054387 0.777240 0.069870 0.041 Uiso 1 1 calc R U . . .
N3 N -0.06329(18) 0.6955(2) 0.23881(13) 0.0481(4) Uani 1 1 d . . . . .
N4 N 0.07822(18) 0.6997(2) 0.33026(13) 0.0455(4) Uani 1 1 d . . . . .
N5 N 0.51673(16) 0.94939(15) 0.33157(11) 0.0328(3) Uani 1 1 d . . . . .
N6 N 0.67540(17) 0.93387(16) 0.40479(12) 0.0369(3) Uani 1 1 d . . . . .
N7 N 0.68023(16) 0.77941(15) 0.46594(11) 0.0315(3) Uani 1 1 d . . . . .
N8 N 0.41478(15) 0.80051(13) 0.34363(10) 0.0249(3) Uani 1 1 d . . . . .
N9 N 0.44967(15) 0.53249(14) 0.45503(10) 0.0252(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 1.3116(17) . ?
C1 N4 1.3256(19) . ?
C1 N8 1.4098(15) . ?
C2 N7 1.3104(16) . ?
C2 N8 1.3441(15) . ?
C2 N9 1.4028(17) . ?
N1 N2 1.3161(15) . ?
N2 N3 1.2985(19) . ?
N2 H2 0.8600 . ?
N3 N4 1.3228(16) . ?
N5 N6 1.2929(15) . ?
N5 N8 1.3508(15) . ?
N6 N7 1.3579(16) . ?
N9 N9 1.245(2) 3_666 ?

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 N4 114.86(12) . . ?
N1 C1 N8 122.46(12) . . ?
N4 C1 N8 122.69(12) . . ?
N7 C2 N8 108.82(11) . . ?
N7 C2 N9 130.25(11) . . ?
N8 C2 N9 120.85(11) . . ?
C1 N1 N2 99.74(11) . . ?
N3 N2 N1 115.06(11) . . ?
N3 N2 H2 122.5 . . ?
N1 N2 H2 122.5 . . ?
N2 N3 N4 106.02(11) . . ?
N3 N4 C1 104.32(12) . . ?
N6 N5 N8 105.91(10) . . ?
N5 N6 N7 111.39(11) . . ?
C2 N7 N6 105.64(11) . . ?
C2 N8 N5 108.23(10) . . ?
C2 N8 C1 130.03(11) . . ?
N5 N8 C1 121.72(10) . . ?
N9 N9 C2 111.22(13) 3_666 . ?

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
N4 C1 N1 N2 0.55(17) . . . . ?
N8 C1 N1 N2 -179.68(12) . . . . ?
C1 N1 N2 N3 -0.86(17) . . . . ?
N1 N2 N3 N4 0.87(19) . . . . ?
N2 N3 N4 C1 -0.44(18) . . . . ?
N1 C1 N4 N3 -0.08(19) . . . . ?
N8 C1 N4 N3 -179.85(13) . . . . ?
N8 N5 N6 N7 -0.61(15) . . . . ?
N8 C2 N7 N6 0.21(15) . . . . ?
N9 C2 N7 N6 177.07(13) . . . . ?
N5 N6 N7 C2 0.26(16) . . . . ?
N7 C2 N8 N5 -0.59(15) . . . . ?
N9 C2 N8 N5 -177.80(11) . . . . ?
N7 C2 N8 C1 -179.21(12) . . . . ?
N9 C2 N8 C1 3.6(2) . . . . ?
N6 N5 N8 C2 0.73(15) . . . . ?
N6 N5 N8 C1 179.49(12) . . . . ?
N1 C1 N8 C2 -138.90(14) . . . . ?
N4 C1 N8 C2 40.9(2) . . . . ?
N1 C1 N8 N5 42.65(19) . . . . ?
N4 C1 N8 N5 -137.60(15) . . . . ?
N7 C2 N9 N9 11.8(2) . . . 3_666 ?
N8 C2 N9 N9 -171.70(13) . . . 3_666 ?

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
N2 H2 N7 0.86 2.10 2.8483(16) 145.6 4_475 yes

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_200612_N18_a
_database_code_depnum_ccdc_archive 'CCDC 2013110'
loop_
_audit_author_name
_audit_author_address
'Zhen Dong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-06-30 deposited with the CCDC.	2020-11-24 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 N18, 2(H2 O), 2(H4 N)'
_chemical_formula_sum            'C4 H12 N20 O2'
_chemical_formula_weight         372.34

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'
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                   6.6694(15)
_cell_length_b                   7.5568(16)
_cell_length_c                   8.9249(18)
_cell_angle_alpha                114.559(5)
_cell_angle_beta                 96.129(7)
_cell_angle_gamma                107.120(6)
_cell_volume                     377.16(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2142
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.31

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6225
_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            1745
_diffrn_reflns_av_unetI/netI     0.1028
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         27.634
_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             1745
_reflns_number_gt                1026
_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)+(0.0624P)²+0.1748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1745
_refine_ls_number_parameters     136
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1366
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.068
_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 0.2638(4) 0.5218(3) 0.5305(3) 0.0249(6) Uani 1 1 d . . . . .
C2 C 0.3520(4) 0.7335(4) 0.3725(3) 0.0295(6) Uani 1 1 d . . . . .
N1 N 0.1584(4) 0.3352(3) 0.5151(3) 0.0360(6) Uani 1 1 d . . . . .
N2 N 0.1965(4) 0.3695(3) 0.6783(3) 0.0391(6) Uani 1 1 d . . . . .
N3 N 0.3164(4) 0.5659(3) 0.7801(3) 0.0442(7) Uani 1 1 d . . . . .
N4 N 0.3635(4) 0.6682(3) 0.6878(3) 0.0385(6) Uani 1 1 d . . . . .
N5 N 0.2674(3) 0.5579(3) 0.3874(2) 0.0264(5) Uani 1 1 d . . . . .
N6 N 0.1711(4) 0.3969(3) 0.2276(3) 0.0378(6) Uani 1 1 d . . . . .
N7 N 0.1994(4) 0.4765(3) 0.1248(3) 0.0457(7) Uani 1 1 d . . . . .
N8 N 0.3124(4) 0.6858(3) 0.2107(3) 0.0402(6) Uani 1 1 d . . . . .
N9 N 0.4609(4) 0.9295(3) 0.5171(3) 0.0399(6) Uani 1 1 d . . . . .
N10 N 0.2760(4) 0.9612(3) 0.0573(3) 0.0319(6) Uani 1 1 d D . . . .
H10A H 0.391(3) 1.061(3) 0.145(2) 0.048 Uiso 1 1 d D U . . .
H10B H 0.159(3) 0.945(4) 0.107(3) 0.048 Uiso 1 1 d D U . . .
H10C H 0.296(4) 0.841(3) 0.016(3) 0.048 Uiso 1 1 d D U . . .
H10D H 0.241(4) 0.997(3) -0.023(2) 0.048 Uiso 1 1 d D U . . .
O1 O 0.9070(4) 0.9492(3) 0.1992(3) 0.0570(7) Uani 1 1 d D . . . .
H1A H 0.962(6) 1.062(3) 0.299(3) 0.086 Uiso 1 1 d D U . . .
H1B H 0.845(6) 0.843(3) 0.217(4) 0.086 Uiso 1 1 d D 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 N4 1.309(3) . ?
C1 N1 1.318(3) . ?
C1 N5 1.413(3) . ?
C2 N8 1.310(3) . ?
C2 N5 1.349(3) . ?
C2 N9 1.401(3) . ?
N1 N2 1.350(3) . ?
N2 N3 1.301(3) . ?
N3 N4 1.348(3) . ?
N5 N6 1.352(3) . ?
N6 N7 1.292(3) . ?
N7 N8 1.351(3) . ?
N9 N9 1.216(4) 2_676 ?
N10 H10A 0.899(14) . ?
N10 H10B 0.937(14) . ?
N10 H10C 0.883(14) . ?
N10 H10D 0.897(14) . ?
O1 H1A 0.879(18) . ?
O1 H1B 0.873(18) . ?

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
N4 C1 N1 114.5(2) . . ?
N4 C1 N5 123.5(2) . . ?
N1 C1 N5 122.0(2) . . ?
N8 C2 N5 109.4(2) . . ?
N8 C2 N9 129.4(2) . . ?
N5 C2 N9 121.1(2) . . ?
C1 N1 N2 102.9(2) . . ?
N3 N2 N1 109.8(2) . . ?
N2 N3 N4 109.5(2) . . ?
C1 N4 N3 103.3(2) . . ?
C2 N5 N6 107.17(19) . . ?
C2 N5 C1 132.5(2) . . ?
N6 N5 C1 120.38(18) . . ?
N7 N6 N5 106.47(18) . . ?
N6 N7 N8 111.5(2) . . ?
C2 N8 N7 105.4(2) . . ?
N9 N9 C2 113.4(3) 2_676 . ?
H10A N10 H10B 104.8(18) . . ?
H10A N10 H10C 109.3(18) . . ?
H10B N10 H10C 107.6(18) . . ?
H10A N10 H10D 114.2(18) . . ?
H10B N10 H10D 107.3(17) . . ?
H10C N10 H10D 113.1(19) . . ?
H1A O1 H1B 107(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
N4 C1 N1 N2 0.1(3) . . . . ?
N5 C1 N1 N2 179.9(2) . . . . ?
C1 N1 N2 N3 0.3(3) . . . . ?
N1 N2 N3 N4 -0.5(3) . . . . ?
N1 C1 N4 N3 -0.4(3) . . . . ?
N5 C1 N4 N3 179.8(2) . . . . ?
N2 N3 N4 C1 0.5(3) . . . . ?
N8 C2 N5 N6 -0.4(3) . . . . ?
N9 C2 N5 N6 179.1(2) . . . . ?
N8 C2 N5 C1 -179.9(2) . . . . ?
N9 C2 N5 C1 -0.4(4) . . . . ?
N4 C1 N5 C2 -4.4(4) . . . . ?
N1 C1 N5 C2 175.8(2) . . . . ?
N4 C1 N5 N6 176.2(2) . . . . ?
N1 C1 N5 N6 -3.6(4) . . . . ?
C2 N5 N6 N7 0.1(3) . . . . ?
C1 N5 N6 N7 179.7(2) . . . . ?
N5 N6 N7 N8 0.2(3) . . . . ?
N5 C2 N8 N7 0.5(3) . . . . ?
N9 C2 N8 N7 -178.9(3) . . . . ?
N6 N7 N8 C2 -0.4(3) . . . . ?
N8 C2 N9 N9 -4.8(5) . . . 2_676 ?
N5 C2 N9 N9 175.8(3) . . . 2_676 ?

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
N10 H10A N3 0.899(14) 2.670(19) 3.376(3) 136.1(18) 2_676 yes
N10 H10A N4 0.899(14) 2.017(15) 2.893(3) 165(2) 2_676 yes
N10 H10B O1 0.937(14) 1.954(14) 2.881(3) 170(2) 1_455 yes
N10 H10C N3 0.883(14) 2.316(17) 3.096(3) 147(2) 1_554 yes
N10 H10C N8 0.883(14) 2.48(2) 2.976(3) 116.2(18) . yes
N10 H10D O1 0.897(14) 2.012(15) 2.892(3) 167(2) 2_675 yes
O1 H1A N1 0.879(18) 2.061(19) 2.923(3) 166(4) 1_665 yes
O1 H1B N2 0.873(18) 2.14(2) 2.975(3) 160(3) 2_666 yes

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_DZ200729_a
_database_code_depnum_ccdc_archive 'CCDC 2020073'
loop_
_audit_author_name
_audit_author_address
'Zhen Dong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-07-30 deposited with the CCDC.	2020-11-24 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 N18, C2 H8 N, H2 O'
_chemical_formula_sum            'C6 H13 N19 O'
_chemical_formula_weight         367.35

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                   8.2241(14)
_cell_length_b                   8.4195(15)
_cell_length_c                   12.477(2)
_cell_angle_alpha                107.695(5)
_cell_angle_beta                 91.553(5)
_cell_angle_gamma                111.931(5)
_cell_volume                     753.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6720
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.42

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6983
_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_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11646
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.704
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3417
_reflns_number_gt                2833
_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 APEX2'
_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)+(0.0477P)²+0.2037P] 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         3417
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.72448(18) 0.08229(17) 0.04894(11) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.71173(18) 0.38830(16) 0.14595(11) 0.0246(3) Uani 1 1 d . . . . .
C3 C 0.72282(18) 0.57386(17) 0.43984(10) 0.0244(3) Uani 1 1 d . . . . .
C4 C 0.78692(18) 0.50237(16) 0.60380(11) 0.0241(3) Uani 1 1 d . . . . .
C5 C 0.5920(2) 0.0329(2) 0.67358(15) 0.0443(4) Uani 1 1 d . . . . .
H5A H 0.603294 0.147068 0.727429 0.066 Uiso 1 1 calc R U . . .
H5B H 0.472659 -0.055359 0.663026 0.066 Uiso 1 1 calc R U . . .
H5C H 0.619121 0.048149 0.602056 0.066 Uiso 1 1 calc R U . . .
C6 C 0.9033(2) 0.0894(2) 0.72871(16) 0.0499(4) Uani 1 1 d . . . . .
H6A H 0.929913 0.100455 0.656221 0.075 Uiso 1 1 calc R U . . .
H6B H 0.976365 0.038445 0.755159 0.075 Uiso 1 1 calc R U . . .
H6C H 0.926352 0.207363 0.782623 0.075 Uiso 1 1 calc R U . . .
N1 N 0.73638(19) 0.02675(16) 0.13577(10) 0.0378(3) Uani 1 1 d . . . . .
N2 N 0.73097(19) -0.14244(16) 0.08575(10) 0.0370(3) Uani 1 1 d . . . . .
N3 N 0.71710(19) -0.17959(16) -0.02424(10) 0.0367(3) Uani 1 1 d . . . . .
N4 N 0.71182(19) -0.03812(16) -0.05097(10) 0.0361(3) Uani 1 1 d . . . . .
N5 N 0.72472(17) 0.25198(15) 0.05660(9) 0.0304(3) Uani 1 1 d . . . . .
N6 N 0.7432(2) 0.30146(18) -0.03942(10) 0.0479(4) Uani 1 1 d . . . . .
N7 N 0.7420(2) 0.45823(19) -0.01378(11) 0.0524(4) Uani 1 1 d . . . . .
N8 N 0.72344(19) 0.51554(16) 0.09726(10) 0.0350(3) Uani 1 1 d . . . . .
H8 H 0.719580 0.618882 0.132345 0.042 Uiso 1 1 calc R U . . .
N9 N 0.69384(16) 0.37952(14) 0.24712(9) 0.0273(3) Uani 1 1 d . . . . .
N10 N 0.69749(15) 0.53732(14) 0.32675(9) 0.0247(2) Uani 1 1 d . . . . .
N11 N 0.66806(18) 0.67473(16) 0.30623(10) 0.0337(3) Uani 1 1 d . . . . .
N12 N 0.67603(19) 0.78832(16) 0.40520(10) 0.0382(3) Uani 1 1 d . . . . .
N13 N 0.70843(18) 0.72977(16) 0.49061(10) 0.0336(3) Uani 1 1 d . . . . .
N14 N 0.75874(16) 0.46377(15) 0.48767(9) 0.0280(3) Uani 1 1 d . . . . .
H14 H 0.764184 0.365600 0.443683 0.034 Uiso 1 1 calc R U . . .
N15 N 0.72591(16) 0.60507(16) 0.68024(9) 0.0306(3) Uani 1 1 d . . . . .
N16 N 0.78807(17) 0.59268(16) 0.77580(9) 0.0316(3) Uani 1 1 d . . . . .
H16 H 0.769722 0.646645 0.841906 0.038 Uiso 1 1 calc R U . . .
N17 N 0.87895(19) 0.49195(18) 0.76067(10) 0.0382(3) Uani 1 1 d . . . . .
N18 N 0.88031(18) 0.43167(17) 0.64984(10) 0.0352(3) Uani 1 1 d . . . . .
N19 N 0.71573(17) -0.03007(16) 0.71669(10) 0.0337(3) Uani 1 1 d . . . . .
H19A H 0.692400 -0.039360 0.784299 0.040 Uiso 1 1 calc R U . . .
H19B H 0.697060 -0.140658 0.669521 0.040 Uiso 1 1 calc R U . . .
O1 O 0.85788(15) 0.17767(14) 0.37794(9) 0.0388(3) Uani 1 1 d . . . . .
H1B H 0.822781 0.134877 0.299713 0.058 Uiso 1 1 d R U . . .
H1A H 0.817281 0.077477 0.400313 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 N4 1.3185(16) . ?
C1 N1 1.3185(17) . ?
C1 N5 1.4018(16) . ?
C2 N9 1.2959(17) . ?
C2 N8 1.3593(17) . ?
C2 N5 1.3754(15) . ?
C3 N13 1.3239(16) . ?
C3 N10 1.3421(16) . ?
C3 N14 1.3541(17) . ?
C4 N15 1.3258(17) . ?
C4 N18 1.3415(18) . ?
C4 N14 1.3778(17) . ?
C5 N19 1.467(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N19 1.466(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N1 N2 1.3533(15) . ?
N2 N3 1.3032(17) . ?
N3 N4 1.3458(16) . ?
N5 N6 1.3777(16) . ?
N6 N7 1.2642(17) . ?
N7 N8 1.3549(17) . ?
N8 H8 0.8600 . ?
N9 N10 1.3854(14) . ?
N10 N11 1.3596(15) . ?
N11 N12 1.2941(16) . ?
N12 N13 1.3607(16) . ?
N14 H14 0.8600 . ?
N15 N16 1.3328(16) . ?
N16 N17 1.3028(17) . ?
N16 H16 0.8600 . ?
N17 N18 1.3223(17) . ?
N19 H19A 0.8900 . ?
N19 H19B 0.8900 . ?
O1 H1B 0.9269 . ?
O1 H1A 0.9159 . ?

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
N4 C1 N1 113.91(11) . . ?
N4 C1 N5 120.58(11) . . ?
N1 C1 N5 125.50(11) . . ?
N9 C2 N8 134.25(12) . . ?
N9 C2 N5 123.78(11) . . ?
N8 C2 N5 101.97(11) . . ?
N13 C3 N10 108.48(11) . . ?
N13 C3 N14 128.75(12) . . ?
N10 C3 N14 122.76(11) . . ?
N15 C4 N18 113.26(12) . . ?
N15 C4 N14 125.91(12) . . ?
N18 C4 N14 120.82(11) . . ?
N19 C5 H5A 109.5 . . ?
N19 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N19 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N19 C6 H6A 109.5 . . ?
N19 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N19 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 N1 N2 103.39(11) . . ?
N3 N2 N1 109.34(11) . . ?
N2 N3 N4 109.95(11) . . ?
C1 N4 N3 103.40(11) . . ?
C2 N5 N6 110.18(10) . . ?
C2 N5 C1 131.80(11) . . ?
N6 N5 C1 118.02(10) . . ?
N7 N6 N5 107.72(11) . . ?
N6 N7 N8 109.00(11) . . ?
N7 N8 C2 111.13(11) . . ?
N7 N8 H8 124.4 . . ?
C2 N8 H8 124.4 . . ?
C2 N9 N10 114.37(10) . . ?
C3 N10 N11 108.52(10) . . ?
C3 N10 N9 124.03(10) . . ?
N11 N10 N9 127.37(10) . . ?
N12 N11 N10 105.87(10) . . ?
N11 N12 N13 111.43(11) . . ?
C3 N13 N12 105.70(11) . . ?
C3 N14 C4 122.78(11) . . ?
C3 N14 H14 118.6 . . ?
C4 N14 H14 118.6 . . ?
C4 N15 N16 100.62(11) . . ?
N17 N16 N15 114.37(11) . . ?
N17 N16 H16 122.8 . . ?
N15 N16 H16 122.8 . . ?
N16 N17 N18 106.44(11) . . ?
N17 N18 C4 105.31(11) . . ?
C6 N19 C5 113.96(13) . . ?
C6 N19 H19A 108.8 . . ?
C5 N19 H19A 108.8 . . ?
C6 N19 H19B 108.8 . . ?
C5 N19 H19B 108.8 . . ?
H19A N19 H19B 107.7 . . ?
H1B O1 H1A 106.0 . . ?

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 H5B O1 0.96 2.49 3.395(2) 156.0 2_656 yes
N19 H19A N4 0.89 2.05 2.9209(17) 164.4 1_556 yes
N19 H19B N13 0.89 2.19 2.9125(17) 138.1 1_545 yes
N19 H19B N15 0.89 2.28 2.9992(17) 137.5 1_545 yes
C6 H6C N17 0.96 2.66 3.373(2) 131.8 . yes
N8 H8 N11 0.86 2.16 2.6829(16) 118.4 . yes
N8 H8 N2 0.86 2.23 2.9044(17) 135.6 1_565 yes
N14 H14 O1 0.86 1.98 2.8043(15) 159.8 . yes
N16 H16 N3 0.86 2.04 2.8720(17) 164.0 1_566 yes
O1 H1A N12 0.92 2.29 3.1847(17) 164.1 1_545 yes
O1 H1B N1 0.93 1.96 2.8805(16) 175.6 . yes

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_DZ200713_a
_database_code_depnum_ccdc_archive 'CCDC 2015888'
loop_
_audit_author_name
_audit_author_address
'Zhen Dong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2020-11-24 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 N18, 2(C H4 N5), 4(H2 O)'
_chemical_formula_sum            'C6 H16 N28 O4'
_chemical_formula_weight         544.47

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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   23.398(5)
_cell_length_b                   5.4052(12)
_cell_length_c                   18.155(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.790(7)
_cell_angle_gamma                90
_cell_volume                     2247.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2612
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      23.43

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6219
_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_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16358
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         0.889
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3958
_reflns_number_gt                2070
_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 APEX2'
_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)+(0.0533P)²] 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         3958
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.40417(14) 0.4539(6) 0.38421(17) 0.0315(8) Uani 1 1 d . . . . .
C2 C 0.47239(14) 0.0830(6) 0.40660(18) 0.0325(8) Uani 1 1 d . . . . .
C3 C 0.09885(13) 0.9289(6) 0.43067(17) 0.0288(8) Uani 1 1 d . . . . .
C4 C 0.03023(14) 0.5621(6) 0.42182(17) 0.0316(8) Uani 1 1 d . . . . .
C5 C 0.66027(15) 0.9889(7) 0.37315(19) 0.0380(9) Uani 1 1 d . . . . .
C6 C 0.84516(14) 0.4518(6) 0.30060(18) 0.0351(9) Uani 1 1 d . . . . .
N1 N 0.40159(13) 0.5172(5) 0.45279(15) 0.0478(8) Uani 1 1 d . . . . .
N2 N 0.36677(12) 0.7183(5) 0.44304(15) 0.0455(8) Uani 1 1 d . . . . .
N3 N 0.35058(12) 0.7676(5) 0.37100(16) 0.0415(8) Uani 1 1 d . . . . .
N4 N 0.37407(12) 0.5998(5) 0.33192(14) 0.0406(7) Uani 1 1 d . . . . .
N5 N 0.43631(11) 0.2502(5) 0.36540(14) 0.0323(7) Uani 1 1 d . . . . .
N6 N 0.43440(12) 0.1985(5) 0.29207(14) 0.0423(8) Uani 1 1 d . . . . .
N7 N 0.46842(13) 0.0094(6) 0.29019(15) 0.0498(8) Uani 1 1 d . . . . .
N8 N 0.49249(12) -0.0666(5) 0.36107(15) 0.0432(8) Uani 1 1 d . . . . .
N9 N 0.48275(11) 0.0849(5) 0.48613(14) 0.0364(7) Uani 1 1 d . . . . .
N10 N 0.09690(11) 1.0215(5) 0.49711(14) 0.0379(7) Uani 1 1 d . . . . .
N11 N 0.13291(12) 1.2186(5) 0.50294(15) 0.0409(7) Uani 1 1 d . . . . .
N12 N 0.15412(12) 1.2384(5) 0.44180(16) 0.0445(8) Uani 1 1 d . . . . .
N13 N 0.13326(12) 1.0533(5) 0.39426(15) 0.0433(8) Uani 1 1 d . . . . .
N14 N 0.06707(11) 0.7209(5) 0.39809(14) 0.0308(7) Uani 1 1 d . . . . .
N15 N 0.06987(12) 0.6570(5) 0.32656(15) 0.0406(7) Uani 1 1 d . . . . .
N16 N 0.03579(13) 0.4664(5) 0.30926(15) 0.0467(8) Uani 1 1 d . . . . .
N17 N 0.01051(12) 0.4013(5) 0.36756(15) 0.0421(8) Uani 1 1 d . . . . .
N18 N 0.01937(11) 0.5762(5) 0.49496(14) 0.0361(7) Uani 1 1 d . . . . .
N19 N 0.63160(13) 1.1526(6) 0.32873(15) 0.0513(8) Uani 1 1 d . . . . .
H19A H 0.614295 1.271608 0.346802 0.062 Uiso 1 1 calc R U . . .
H19B H 0.629788 1.142828 0.281027 0.062 Uiso 1 1 calc R U . . .
N20 N 0.68994(13) 0.7929(6) 0.35586(17) 0.0494(8) Uani 1 1 d . . . . .
H20 H 0.693033 0.753485 0.310950 0.059 Uiso 1 1 calc R U . . .
N21 N 0.71457(14) 0.6643(6) 0.4189(2) 0.0665(10) Uani 1 1 d . . . . .
N22 N 0.70125(15) 0.7756(7) 0.47470(19) 0.0672(10) Uani 1 1 d . . . . .
N23 N 0.66776(12) 0.9746(6) 0.44808(15) 0.0477(8) Uani 1 1 d . . . . .
H23 H 0.653363 1.077120 0.475629 0.057 Uiso 1 1 calc R U . . .
N25 N 0.87410(12) 0.6178(5) 0.27050(15) 0.0450(8) Uani 1 1 d . . . . .
H25A H 0.877308 0.603316 0.224346 0.054 Uiso 1 1 calc R U . . .
H25B H 0.889903 0.741326 0.296880 0.054 Uiso 1 1 calc R U . . .
N27 N 0.80273(14) 0.2453(6) 0.37976(19) 0.0551(9) Uani 1 1 d . . . . .
N28 N 0.79169(13) 0.1277(6) 0.3179(2) 0.0581(9) Uani 1 1 d . . . . .
N29 N 0.81806(12) 0.2502(5) 0.26867(16) 0.0450(8) Uani 1 1 d . . . . .
H29 H 0.817375 0.204053 0.223161 0.054 Uiso 1 1 calc R U . . .
N30 N 0.83535(12) 0.4460(5) 0.37083(15) 0.0417(8) Uani 1 1 d . . . . .
H30 H 0.847914 0.553862 0.405149 0.050 Uiso 1 1 calc R U . . .
O1 O 0.93935(12) 0.9618(5) 0.36627(13) 0.0549(7) Uani 1 1 d G . . . .
H1A H 0.961308 1.078722 0.357506 0.082 Uiso 1 1 d G U . . .
H1B H 0.932909 0.993815 0.409686 0.082 Uiso 1 1 d G U . . .
O2 O 0.22600(12) 1.5156(5) 0.36617(13) 0.0612(8) Uani 1 1 d G . . . .
H2A H 0.251717 1.601117 0.395073 0.092 Uiso 1 1 d G U . . .
H2B H 0.206392 1.448636 0.395406 0.092 Uiso 1 1 d G U . . .
O3 O 0.71842(12) 0.6472(5) 0.22359(13) 0.0563(7) Uani 1 1 d G . . . .
H3A H 0.732616 0.755410 0.198453 0.084 Uiso 1 1 d G U . . .
H3B H 0.704005 0.538264 0.191324 0.084 Uiso 1 1 d G U . . .
O4 O 0.56481(13) 0.4898(5) 0.39122(13) 0.0642(8) Uani 1 1 d G . . . .
H4A H 0.544606 0.612374 0.371344 0.096 Uiso 1 1 d G U . . .
H4B H 0.569688 0.515106 0.438304 0.096 Uiso 1 1 d G 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 1.304(4) . ?
C1 N4 1.322(4) . ?
C1 N5 1.414(4) . ?
C2 N8 1.310(4) . ?
C2 N5 1.353(4) . ?
C2 N9 1.414(4) . ?
C3 N10 1.315(4) . ?
C3 N13 1.325(4) . ?
C3 N14 1.410(4) . ?
C4 N17 1.324(4) . ?
C4 N14 1.348(4) . ?
C4 N18 1.404(4) . ?
C5 N19 1.289(4) . ?
C5 N23 1.338(4) . ?
C5 N20 1.339(4) . ?
C6 N25 1.309(4) . ?
C6 N29 1.332(4) . ?
C6 N30 1.341(4) . ?
N1 N2 1.348(4) . ?
N2 N3 1.313(3) . ?
N3 N4 1.337(3) . ?
N5 N6 1.352(3) . ?
N6 N7 1.300(4) . ?
N7 N8 1.358(3) . ?
N9 N9 1.257(5) 3_656 ?
N10 N11 1.349(3) . ?
N11 N12 1.310(3) . ?
N12 N13 1.346(4) . ?
N14 N15 1.358(3) . ?
N15 N16 1.301(3) . ?
N16 N17 1.360(3) . ?
N18 N18 1.265(5) 3_566 ?
N19 H19A 0.8600 . ?
N19 H19B 0.8600 . ?
N20 N21 1.362(4) . ?
N20 H20 0.8600 . ?
N21 N22 1.271(4) . ?
N22 N23 1.360(4) . ?
N23 H23 0.8600 . ?
N25 H25A 0.8600 . ?
N25 H25B 0.8600 . ?
N27 N28 1.271(4) . ?
N27 N30 1.355(4) . ?
N28 N29 1.357(4) . ?
N29 H29 0.8600 . ?
N30 H30 0.8600 . ?
O1 H1A 0.8501 . ?
O1 H1B 0.8499 . ?
O2 H2A 0.8498 . ?
O2 H2B 0.8500 . ?
O3 H3A 0.8501 . ?
O3 H3B 0.8501 . ?
O4 H4A 0.8501 . ?
O4 H4B 0.8501 . ?

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 N4 114.0(3) . . ?
N1 C1 N5 124.4(3) . . ?
N4 C1 N5 121.5(3) . . ?
N8 C2 N5 109.1(3) . . ?
N8 C2 N9 129.8(3) . . ?
N5 C2 N9 121.1(3) . . ?
N10 C3 N13 113.8(3) . . ?
N10 C3 N14 125.0(3) . . ?
N13 C3 N14 121.2(3) . . ?
N17 C4 N14 109.2(3) . . ?
N17 C4 N18 129.5(3) . . ?
N14 C4 N18 121.3(3) . . ?
N19 C5 N23 128.3(3) . . ?
N19 C5 N20 128.7(3) . . ?
N23 C5 N20 103.1(3) . . ?
N25 C6 N29 128.3(3) . . ?
N25 C6 N30 128.1(3) . . ?
N29 C6 N30 103.6(3) . . ?
C1 N1 N2 103.4(3) . . ?
N3 N2 N1 109.8(3) . . ?
N2 N3 N4 108.9(3) . . ?
C1 N4 N3 103.9(2) . . ?
N6 N5 C2 107.3(2) . . ?
N6 N5 C1 119.1(3) . . ?
C2 N5 C1 133.6(3) . . ?
N7 N6 N5 106.9(2) . . ?
N6 N7 N8 110.5(2) . . ?
C2 N8 N7 106.2(3) . . ?
N9 N9 C2 111.5(3) 3_656 . ?
C3 N10 N11 103.5(2) . . ?
N12 N11 N10 109.7(2) . . ?
N11 N12 N13 109.4(2) . . ?
C3 N13 N12 103.6(3) . . ?
C4 N14 N15 107.6(3) . . ?
C4 N14 C3 133.7(3) . . ?
N15 N14 C3 118.7(3) . . ?
N16 N15 N14 106.6(2) . . ?
N15 N16 N17 111.1(2) . . ?
C4 N17 N16 105.6(3) . . ?
N18 N18 C4 112.0(3) 3_566 . ?
C5 N19 H19A 120.0 . . ?
C5 N19 H19B 120.0 . . ?
H19A N19 H19B 120.0 . . ?
C5 N20 N21 111.0(3) . . ?
C5 N20 H20 124.5 . . ?
N21 N20 H20 124.5 . . ?
N22 N21 N20 107.3(3) . . ?
N21 N22 N23 108.0(3) . . ?
C5 N23 N22 110.7(3) . . ?
C5 N23 H23 124.7 . . ?
N22 N23 H23 124.7 . . ?
C6 N25 H25A 120.0 . . ?
C6 N25 H25B 120.0 . . ?
H25A N25 H25B 120.0 . . ?
N28 N27 N30 108.2(3) . . ?
N27 N28 N29 107.5(3) . . ?
C6 N29 N28 110.6(3) . . ?
C6 N29 H29 124.7 . . ?
N28 N29 H29 124.7 . . ?
C6 N30 N27 110.0(3) . . ?
C6 N30 H30 125.0 . . ?
N27 N30 H30 125.0 . . ?
H1A O1 H1B 104.5 . . ?
H2A O2 H2B 104.5 . . ?
H3A O3 H3B 104.5 . . ?
H4A O4 H4B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 N1 N2 0.4(4) . . . . ?
N5 C1 N1 N2 179.8(3) . . . . ?
C1 N1 N2 N3 -0.5(4) . . . . ?
N1 N2 N3 N4 0.3(4) . . . . ?
N1 C1 N4 N3 -0.2(4) . . . . ?
N5 C1 N4 N3 -179.6(3) . . . . ?
N2 N3 N4 C1 -0.1(3) . . . . ?
N8 C2 N5 N6 0.3(4) . . . . ?
N9 C2 N5 N6 -178.8(3) . . . . ?
N8 C2 N5 C1 -178.3(3) . . . . ?
N9 C2 N5 C1 2.6(5) . . . . ?
N1 C1 N5 N6 178.2(3) . . . . ?
N4 C1 N5 N6 -2.5(4) . . . . ?
N1 C1 N5 C2 -3.3(5) . . . . ?
N4 C1 N5 C2 176.0(3) . . . . ?
C2 N5 N6 N7 -0.5(3) . . . . ?
C1 N5 N6 N7 178.4(3) . . . . ?
N5 N6 N7 N8 0.5(4) . . . . ?
N5 C2 N8 N7 0.0(4) . . . . ?
N9 C2 N8 N7 179.0(3) . . . . ?
N6 N7 N8 C2 -0.3(4) . . . . ?
N8 C2 N9 N9 0.9(5) . . . 3_656 ?
N5 C2 N9 N9 179.8(3) . . . 3_656 ?
N13 C3 N10 N11 -0.1(4) . . . . ?
N14 C3 N10 N11 -178.7(3) . . . . ?
C3 N10 N11 N12 0.5(3) . . . . ?
N10 N11 N12 N13 -0.7(4) . . . . ?
N10 C3 N13 N12 -0.3(4) . . . . ?
N14 C3 N13 N12 178.3(3) . . . . ?
N11 N12 N13 C3 0.6(4) . . . . ?
N17 C4 N14 N15 0.4(3) . . . . ?
N18 C4 N14 N15 178.2(3) . . . . ?
N17 C4 N14 C3 178.0(3) . . . . ?
N18 C4 N14 C3 -4.2(5) . . . . ?
N10 C3 N14 C4 -2.3(5) . . . . ?
N13 C3 N14 C4 179.2(3) . . . . ?
N10 C3 N14 N15 175.0(3) . . . . ?
N13 C3 N14 N15 -3.5(4) . . . . ?
C4 N14 N15 N16 -0.1(3) . . . . ?
C3 N14 N15 N16 -178.1(3) . . . . ?
N14 N15 N16 N17 -0.2(4) . . . . ?
N14 C4 N17 N16 -0.5(3) . . . . ?
N18 C4 N17 N16 -178.1(3) . . . . ?
N15 N16 N17 C4 0.4(4) . . . . ?
N17 C4 N18 N18 -7.4(5) . . . 3_566 ?
N14 C4 N18 N18 175.3(3) . . . 3_566 ?
N19 C5 N20 N21 179.8(4) . . . . ?
N23 C5 N20 N21 0.0(4) . . . . ?
C5 N20 N21 N22 -0.3(4) . . . . ?
N20 N21 N22 N23 0.5(4) . . . . ?
N19 C5 N23 N22 -179.5(4) . . . . ?
N20 C5 N23 N22 0.3(4) . . . . ?
N21 N22 N23 C5 -0.5(4) . . . . ?
N30 N27 N28 N29 1.0(4) . . . . ?
N25 C6 N29 N28 -178.4(3) . . . . ?
N30 C6 N29 N28 1.0(4) . . . . ?
N27 N28 N29 C6 -1.3(4) . . . . ?
N25 C6 N30 N27 179.1(3) . . . . ?
N29 C6 N30 N27 -0.4(3) . . . . ?
N28 N27 N30 C6 -0.4(4) . . . . ?

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
N19 H19A O4 0.86 1.94 2.789(4) 168.8 1_565 yes
N19 H19B N4 0.86 2.05 2.906(4) 177.0 2_655 yes
N20 H20 O3 0.86 1.89 2.736(4) 166.2 . yes
N23 H23 N2 0.86 1.98 2.823(4) 167.5 3_676 yes
N25 H25A N13 0.86 2.13 2.981(4) 168.4 2_645 yes
N25 H25B O1 0.86 1.94 2.780(3) 166.4 . yes
N29 H29 O2 0.86 2.01 2.763(4) 146.2 2_635 yes
N30 H30 N11 0.86 2.05 2.897(4) 169.5 3_676 yes

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.243
_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_DZ200624_K_a
_database_code_depnum_ccdc_archive 'CCDC 2013111'
loop_
_audit_author_name
_audit_author_address
'Zhen Dong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-06-30 deposited with the CCDC.	2020-11-24 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         'C2 H2 K N9 O'
_chemical_formula_sum            'C2 H2 K N9 O'
_chemical_formula_weight         207.23

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'
K K 0.2009 0.2494 '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                   6.7396(5)
_cell_length_b                   7.7275(5)
_cell_length_c                   8.6497(6)
_cell_angle_alpha                100.429(2)
_cell_angle_beta                 107.356(2)
_cell_angle_gamma                114.906(2)
_cell_volume                     364.70(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3522
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.704
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6468
_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 ?
_diffrn_reflns_number            5663
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.638
_diffrn_reflns_theta_max         27.638
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1679
_reflns_number_gt                1457
_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)+(0.0398P)²+0.1082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1679
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.6905(3) 0.4646(2) 0.44922(19) 0.0245(3) Uani 1 1 d . . . . .
C2 C 0.9992(3) 0.8385(2) 0.61457(19) 0.0257(3) Uani 1 1 d . . . . .
K1 K 0.33215(6) -0.25618(5) 0.18647(4) 0.03450(13) Uani 1 1 d . . . . .
N1 N 0.6082(3) 0.2800(2) 0.45853(18) 0.0354(3) Uani 1 1 d . . . . .
N2 N 0.4295(3) 0.1602(2) 0.29877(19) 0.0379(3) Uani 1 1 d . . . . .
N3 N 0.4121(3) 0.2717(2) 0.20419(18) 0.0373(3) Uani 1 1 d . . . . .
N4 N 0.5784(3) 0.4705(2) 0.29855(17) 0.0332(3) Uani 1 1 d . . . . .
N5 N 0.8816(2) 0.63905(17) 0.59313(15) 0.0243(3) Uani 1 1 d . . . . .
N6 N 0.9851(2) 0.6202(2) 0.74354(17) 0.0330(3) Uani 1 1 d . . . . .
N7 N 1.1579(2) 0.8026(2) 0.84924(18) 0.0348(3) Uani 1 1 d . . . . .
N8 N 1.1721(2) 0.94216(19) 0.77247(17) 0.0321(3) Uani 1 1 d . . . . .
N9 N 0.9291(3) 0.90866(19) 0.48168(17) 0.0335(3) Uani 1 1 d . . . . .
O1 O -0.1569(3) -0.3688(2) 0.07547(17) 0.0422(3) Uani 1 1 d . . . . .
H1A H -0.212(4) -0.384(4) 0.144(3) 0.063 Uiso 1 1 d . U . . .
H1B H -0.203(4) -0.298(4) 0.029(3) 0.063 Uiso 1 1 d . 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 N4 1.3172(19) . ?
C1 N1 1.3235(19) . ?
C1 N5 1.4140(19) . ?
C2 N8 1.316(2) . ?
C2 N5 1.3481(18) . ?
C2 N9 1.3987(19) . ?
K1 O1 2.8174(15) . ?
K1 O1 2.8408(14) 2_545 ?
K1 N2 2.9046(14) . ?
K1 N7 2.9964(14) 1_444 ?
K1 N1 3.0256(14) 2_656 ?
K1 N6 3.0289(13) 2_656 ?
K1 N8 3.0541(14) 2_766 ?
K1 N4 3.2994(14) 1_545 ?
K1 K1 4.1741(7) 2_545 ?
N1 N2 1.350(2) . ?
N2 N3 1.307(2) . ?
N3 N4 1.3538(19) . ?
N5 N6 1.3466(17) . ?
N6 N7 1.3015(19) . ?
N7 N8 1.3505(18) . ?
N9 N9 1.236(2) 2_776 ?
O1 H1A 0.79(3) . ?
O1 H1B 0.84(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
N4 C1 N1 114.73(13) . . ?
N4 C1 N5 123.97(13) . . ?
N1 C1 N5 121.29(13) . . ?
N8 C2 N5 109.51(13) . . ?
N8 C2 N9 129.37(13) . . ?
N5 C2 N9 121.10(13) . . ?
O1 K1 O1 84.93(4) . 2_545 ?
O1 K1 N2 85.33(4) . . ?
O1 K1 N2 151.98(4) 2_545 . ?
O1 K1 N7 69.97(4) . 1_444 ?
O1 K1 N7 74.27(4) 2_545 1_444 ?
N2 K1 N7 77.71(4) . 1_444 ?
O1 K1 N1 94.27(4) . 2_656 ?
O1 K1 N1 114.85(4) 2_545 2_656 ?
N2 K1 N1 92.04(4) . 2_656 ?
N7 K1 N1 161.62(4) 1_444 2_656 ?
O1 K1 N6 63.43(4) . 2_656 ?
O1 K1 N6 67.96(4) 2_545 2_656 ?
N2 K1 N6 129.09(4) . 2_656 ?
N7 K1 N6 121.17(4) 1_444 2_656 ?
N1 K1 N6 54.69(4) 2_656 2_656 ?
O1 K1 N8 145.47(4) . 2_766 ?
O1 K1 N8 109.76(4) 2_545 2_766 ?
N2 K1 N8 66.93(4) . 2_766 ?
N7 K1 N8 83.81(4) 1_444 2_766 ?
N1 K1 N8 106.37(4) 2_656 2_766 ?
N6 K1 N8 150.78(4) 2_656 2_766 ?
O1 K1 N4 127.60(4) . 1_545 ?
O1 K1 N4 64.44(4) 2_545 1_545 ?
N2 K1 N4 139.55(4) . 1_545 ?
N7 K1 N4 131.18(4) 1_444 1_545 ?
N1 K1 N4 65.83(4) 2_656 1_545 ?
N6 K1 N4 65.86(4) 2_656 1_545 ?
N8 K1 N4 86.55(4) 2_766 1_545 ?
O1 K1 K1 42.68(3) . 2_545 ?
O1 K1 K1 42.25(3) 2_545 2_545 ?
N2 K1 K1 123.08(3) . 2_545 ?
N7 K1 K1 65.44(3) 1_444 2_545 ?
N1 K1 K1 109.65(3) 2_656 2_545 ?
N6 K1 K1 56.14(3) 2_656 2_545 ?
N8 K1 K1 141.83(3) 2_766 2_545 ?
N4 K1 K1 96.79(3) 1_545 2_545 ?
C1 N1 N2 102.75(13) . . ?
C1 N1 K1 116.38(10) . 2_656 ?
N2 N1 K1 132.46(10) . 2_656 ?
N3 N2 N1 109.95(12) . . ?
N3 N2 K1 128.06(10) . . ?
N1 N2 K1 114.66(10) . . ?
N2 N3 N4 109.69(13) . . ?
C1 N4 N3 102.87(12) . . ?
C1 N4 K1 132.95(10) . 1_565 ?
N3 N4 K1 107.69(9) . 1_565 ?
N6 N5 C2 107.26(12) . . ?
N6 N5 C1 120.31(12) . . ?
C2 N5 C1 132.40(12) . . ?
N7 N6 N5 106.71(11) . . ?
N7 N6 K1 130.64(9) . 2_656 ?
N5 N6 K1 115.92(9) . 2_656 ?
N6 N7 N8 111.16(12) . . ?
N6 N7 K1 103.61(8) . 1_666 ?
N8 N7 K1 144.73(10) . 1_666 ?
C2 N8 N7 105.36(12) . . ?
C2 N8 K1 117.69(10) . 2_766 ?
N7 N8 K1 118.39(9) . 2_766 ?
N9 N9 C2 111.99(16) 2_776 . ?
K1 O1 K1 95.07(4) . 2_545 ?
K1 O1 H1A 117.1(18) . . ?
K1 O1 H1A 112.4(18) 2_545 . ?
K1 O1 H1B 118.3(16) . . ?
K1 O1 H1B 108.4(17) 2_545 . ?
H1A O1 H1B 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
N4 C1 N1 N2 0.35(18) . . . . ?
N5 C1 N1 N2 179.37(13) . . . . ?
N4 C1 N1 K1 -151.87(11) . . . 2_656 ?
N5 C1 N1 K1 27.15(18) . . . 2_656 ?
C1 N1 N2 N3 0.04(18) . . . . ?
K1 N1 N2 N3 145.58(12) 2_656 . . . ?
C1 N1 N2 K1 152.69(10) . . . . ?
K1 N1 N2 K1 -61.77(15) 2_656 . . . ?
N1 N2 N3 N4 -0.40(19) . . . . ?
K1 N2 N3 N4 -148.38(11) . . . . ?
N1 C1 N4 N3 -0.58(18) . . . . ?
N5 C1 N4 N3 -179.57(13) . . . . ?
N1 C1 N4 K1 129.11(13) . . . 1_565 ?
N5 C1 N4 K1 -49.9(2) . . . 1_565 ?
N2 N3 N4 C1 0.57(18) . . . . ?
N2 N3 N4 K1 -143.19(11) . . . 1_565 ?
N8 C2 N5 N6 0.41(17) . . . . ?
N9 C2 N5 N6 -178.19(13) . . . . ?
N8 C2 N5 C1 -177.51(14) . . . . ?
N9 C2 N5 C1 3.9(2) . . . . ?
N4 C1 N5 N6 179.25(14) . . . . ?
N1 C1 N5 N6 0.3(2) . . . . ?
N4 C1 N5 C2 -3.1(3) . . . . ?
N1 C1 N5 C2 178.02(15) . . . . ?
C2 N5 N6 N7 -0.11(16) . . . . ?
C1 N5 N6 N7 178.11(13) . . . . ?
C2 N5 N6 K1 154.31(9) . . . 2_656 ?
C1 N5 N6 K1 -27.47(16) . . . 2_656 ?
N5 N6 N7 N8 -0.21(17) . . . . ?
K1 N6 N7 N8 -149.43(11) 2_656 . . . ?
N5 N6 N7 K1 173.77(9) . . . 1_666 ?
K1 N6 N7 K1 24.55(14) 2_656 . . 1_666 ?
N5 C2 N8 N7 -0.52(17) . . . . ?
N9 C2 N8 N7 177.93(16) . . . . ?
N5 C2 N8 K1 134.00(10) . . . 2_766 ?
N9 C2 N8 K1 -47.6(2) . . . 2_766 ?
N6 N7 N8 C2 0.46(18) . . . . ?
K1 N7 N8 C2 -169.38(14) 1_666 . . . ?
N6 N7 N8 K1 -133.68(11) . . . 2_766 ?
K1 N7 N8 K1 56.5(2) 1_666 . . 2_766 ?
N8 C2 N9 N9 8.2(3) . . . 2_776 ?
N5 C2 N9 N9 -173.48(17) . . . 2_776 ?

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 0.79(3) 2.32(3) 3.0827(19) 163(2) 1_445 yes
O1 H1B N3 0.84(3) 2.19(3) 2.938(2) 149(2) 2 yes

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_DZ200723_a
_database_code_depnum_ccdc_archive 'CCDC 2020075'
loop_
_audit_author_name
_audit_author_address
'Zhen Dong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-07-30 deposited with the CCDC.	2020-11-24 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 H N18, 3(H5 N2)'
_chemical_formula_sum            'C4 H16 N24'
_chemical_formula_weight         400.41

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                   7.1132(8)
_cell_length_b                   10.6476(12)
_cell_length_c                   10.9222(12)
_cell_angle_alpha                83.385(4)
_cell_angle_beta                 72.037(3)
_cell_angle_gamma                79.277(4)
_cell_volume                     771.69(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6701
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.53

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5990
_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_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11622
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0452
_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         1.964
_diffrn_reflns_theta_max         27.608
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3520
_reflns_number_gt                2924
_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 APEX2'
_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)+(0.0957P)²+0.2185P] 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         3520
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.2595(2) 0.22282(15) 0.68687(15) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.2167(2) 0.43620(15) 0.56644(16) 0.0195(3) Uani 1 1 d . . . . .
C3 C 0.4599(2) 0.51673(15) 0.25007(15) 0.0197(3) Uani 1 1 d . . . . .
C4 C 0.3580(2) 0.74084(15) 0.17559(16) 0.0207(3) Uani 1 1 d . . . . .
N1 N 0.3658(2) 0.14964(13) 0.59115(13) 0.0252(3) Uani 1 1 d . . . . .
N2 N 0.4159(2) 0.03654(14) 0.65373(15) 0.0279(4) Uani 1 1 d . . . . .
N3 N 0.3415(2) 0.04529(14) 0.77783(15) 0.0291(4) Uani 1 1 d . . . . .
N4 N 0.2407(2) 0.16357(13) 0.80254(14) 0.0257(3) Uani 1 1 d . . . . .
N5 N 0.1767(2) 0.34997(13) 0.67037(13) 0.0221(3) Uani 1 1 d . . . . .
N6 N 0.0512(2) 0.41479(14) 0.77647(14) 0.0285(4) Uani 1 1 d . . . . .
N7 N 0.0198(2) 0.53190(14) 0.73606(15) 0.0309(4) Uani 1 1 d . . . . .
N8 N 0.1171(2) 0.55188(14) 0.60850(14) 0.0256(3) Uani 1 1 d . . . . .
N9 N 0.3292(2) 0.40692(13) 0.44961(13) 0.0221(3) Uani 1 1 d . . . . .
N10 N 0.3371(2) 0.52082(13) 0.36929(14) 0.0269(3) Uani 1 1 d . . . . .
H10 H 0.263631 0.591461 0.397137 0.032 Uiso 1 1 calc R U . . .
N11 N 0.5919(2) 0.41789(14) 0.19668(14) 0.0262(3) Uani 1 1 d . . . . .
N12 N 0.6882(2) 0.46422(15) 0.07606(15) 0.0296(4) Uani 1 1 d . . . . .
N13 N 0.6226(2) 0.58190(14) 0.05282(14) 0.0265(3) Uani 1 1 d . . . . .
N14 N 0.4728(2) 0.61874(13) 0.16252(13) 0.0210(3) Uani 1 1 d . . . . .
N15 N 0.3392(2) 0.82328(14) 0.07843(15) 0.0302(4) Uani 1 1 d . . . . .
N16 N 0.2180(3) 0.92560(15) 0.13820(17) 0.0354(4) Uani 1 1 d . . . . .
N17 N 0.1678(3) 0.90147(15) 0.26320(17) 0.0360(4) Uani 1 1 d . . . . .
N18 N 0.2570(2) 0.78268(14) 0.29051(15) 0.0307(4) Uani 1 1 d . . . . .
N19 N 0.9122(2) 0.16465(14) 0.12036(14) 0.0260(3) Uani 1 1 d . . . . .
H19A H 0.989049 0.088728 0.122584 0.039 Uiso 1 1 d R U . . .
H19B H 0.820270 0.159115 0.082259 0.039 Uiso 1 1 d R U . . .
N20 N 1.0345(2) 0.25780(14) 0.04839(14) 0.0273(3) Uani 1 1 d . . . . .
H20A H 0.956784 0.332511 0.041492 0.041 Uiso 1 1 calc R U . . .
H20B H 1.100865 0.231187 -0.029940 0.041 Uiso 1 1 calc R U . . .
H20C H 1.121209 0.267207 0.089172 0.041 Uiso 1 1 calc R U . . .
N21 N 0.3309(2) 0.20272(15) 0.19257(14) 0.0282(4) Uani 1 1 d . . . . .
H21A H 0.390445 0.127854 0.159441 0.042 Uiso 1 1 d R U . . .
H21B H 0.413058 0.260183 0.162787 0.042 Uiso 1 1 d R U . . .
N22 N 0.2835(2) 0.18745(14) 0.33141(14) 0.0254(3) Uani 1 1 d . . . . .
H22A H 0.287288 0.260593 0.361975 0.038 Uiso 1 1 calc R U . . .
H22B H 0.372430 0.125658 0.353212 0.038 Uiso 1 1 calc R U . . .
H22C H 0.161454 0.166706 0.364549 0.038 Uiso 1 1 calc R U . . .
N23 N 0.2632(2) 0.78254(14) 0.60976(15) 0.0259(3) Uani 1 1 d . . . . .
H23A H 0.386296 0.796702 0.566042 0.039 Uiso 1 1 calc R U . . .
H23B H 0.248587 0.704696 0.595782 0.039 Uiso 1 1 calc R U . . .
H23C H 0.243710 0.787938 0.693606 0.039 Uiso 1 1 calc R U . . .
N24 N 0.1202(2) 0.87618(14) 0.56773(15) 0.0286(4) Uani 1 1 d . . . . .
H24A H 0.156596 0.883226 0.481939 0.043 Uiso 1 1 d R U . . .
H24B H 0.115739 0.951345 0.597588 0.043 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 1.324(2) . ?
C1 N4 1.325(2) . ?
C1 N5 1.387(2) . ?
C2 N9 1.317(2) . ?
C2 N8 1.355(2) . ?
C2 N5 1.368(2) . ?
C3 N10 1.326(2) . ?
C3 N11 1.329(2) . ?
C3 N14 1.359(2) . ?
C4 N18 1.320(2) . ?
C4 N15 1.321(2) . ?
C4 N14 1.397(2) . ?
N1 N2 1.3584(19) . ?
N2 N3 1.302(2) . ?
N3 N4 1.340(2) . ?
N5 N6 1.3904(19) . ?
N6 N7 1.277(2) . ?
N7 N8 1.363(2) . ?
N9 N10 1.4119(19) . ?
N10 H10 0.8600 . ?
N11 N12 1.366(2) . ?
N12 N13 1.278(2) . ?
N13 N14 1.3751(19) . ?
N15 N16 1.350(2) . ?
N16 N17 1.308(2) . ?
N17 N18 1.350(2) . ?
N19 N20 1.441(2) . ?
N19 H19A 0.8900 . ?
N19 H19B 0.8900 . ?
N20 H20A 0.8900 . ?
N20 H20B 0.8900 . ?
N20 H20C 0.8900 . ?
N21 N22 1.445(2) . ?
N21 H21A 0.8900 . ?
N21 H21B 0.8900 . ?
N22 H22A 0.8900 . ?
N22 H22B 0.8900 . ?
N22 H22C 0.8900 . ?
N23 N24 1.430(2) . ?
N23 H23A 0.8900 . ?
N23 H23B 0.8900 . ?
N23 H23C 0.8900 . ?
N24 H24A 0.8900 . ?
N24 H24B 0.8900 . ?

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 N4 113.50(14) . . ?
N1 C1 N5 124.29(15) . . ?
N4 C1 N5 122.20(14) . . ?
N9 C2 N8 128.80(15) . . ?
N9 C2 N5 124.63(14) . . ?
N8 C2 N5 106.56(14) . . ?
N10 C3 N11 127.55(15) . . ?
N10 C3 N14 123.75(15) . . ?
N11 C3 N14 108.68(14) . . ?
N18 C4 N15 114.29(15) . . ?
N18 C4 N14 121.02(15) . . ?
N15 C4 N14 124.68(15) . . ?
C1 N1 N2 102.86(13) . . ?
N3 N2 N1 110.08(13) . . ?
N2 N3 N4 109.49(14) . . ?
C1 N4 N3 104.07(14) . . ?
C2 N5 C1 131.03(14) . . ?
C2 N5 N6 108.55(13) . . ?
C1 N5 N6 119.72(13) . . ?
N7 N6 N5 105.89(14) . . ?
N6 N7 N8 112.58(14) . . ?
C2 N8 N7 106.42(14) . . ?
C2 N9 N10 108.12(13) . . ?
C3 N10 N9 118.69(14) . . ?
C3 N10 H10 120.7 . . ?
N9 N10 H10 120.7 . . ?
C3 N11 N12 104.88(13) . . ?
N13 N12 N11 112.96(14) . . ?
N12 N13 N14 105.66(13) . . ?
C3 N14 N13 107.79(13) . . ?
C3 N14 C4 128.33(14) . . ?
N13 N14 C4 123.88(14) . . ?
C4 N15 N16 102.94(15) . . ?
N17 N16 N15 110.04(14) . . ?
N16 N17 N18 109.38(15) . . ?
C4 N18 N17 103.34(14) . . ?
N20 N19 H19A 109.4 . . ?
N20 N19 H19B 109.4 . . ?
H19A N19 H19B 109.5 . . ?
N19 N20 H20A 109.5 . . ?
N19 N20 H20B 109.5 . . ?
H20A N20 H20B 109.5 . . ?
N19 N20 H20C 109.5 . . ?
H20A N20 H20C 109.5 . . ?
H20B N20 H20C 109.5 . . ?
N22 N21 H21A 109.1 . . ?
N22 N21 H21B 109.3 . . ?
H21A N21 H21B 109.5 . . ?
N21 N22 H22A 109.5 . . ?
N21 N22 H22B 109.5 . . ?
H22A N22 H22B 109.5 . . ?
N21 N22 H22C 109.5 . . ?
H22A N22 H22C 109.5 . . ?
H22B N22 H22C 109.5 . . ?
N24 N23 H23A 109.5 . . ?
N24 N23 H23B 109.5 . . ?
H23A N23 H23B 109.5 . . ?
N24 N23 H23C 109.5 . . ?
H23A N23 H23C 109.5 . . ?
H23B N23 H23C 109.5 . . ?
N23 N24 H24A 109.3 . . ?
N23 N24 H24B 109.3 . . ?
H24A N24 H24B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 N1 N2 -0.04(19) . . . . ?
N5 C1 N1 N2 179.08(15) . . . . ?
C1 N1 N2 N3 0.21(18) . . . . ?
N1 N2 N3 N4 -0.3(2) . . . . ?
N1 C1 N4 N3 -0.13(19) . . . . ?
N5 C1 N4 N3 -179.27(14) . . . . ?
N2 N3 N4 C1 0.25(19) . . . . ?
N9 C2 N5 C1 10.7(3) . . . . ?
N8 C2 N5 C1 -170.16(16) . . . . ?
N9 C2 N5 N6 -179.14(16) . . . . ?
N8 C2 N5 N6 0.01(18) . . . . ?
N1 C1 N5 C2 -17.1(3) . . . . ?
N4 C1 N5 C2 161.99(17) . . . . ?
N1 C1 N5 N6 173.68(16) . . . . ?
N4 C1 N5 N6 -7.3(2) . . . . ?
C2 N5 N6 N7 0.20(19) . . . . ?
C1 N5 N6 N7 171.67(15) . . . . ?
N5 N6 N7 N8 -0.3(2) . . . . ?
N9 C2 N8 N7 178.90(17) . . . . ?
N5 C2 N8 N7 -0.20(18) . . . . ?
N6 N7 N8 C2 0.4(2) . . . . ?
N8 C2 N9 N10 1.7(2) . . . . ?
N5 C2 N9 N10 -179.33(15) . . . . ?
N11 C3 N10 N9 -5.2(3) . . . . ?
N14 C3 N10 N9 176.70(14) . . . . ?
C2 N9 N10 C3 172.76(15) . . . . ?
N10 C3 N11 N12 -176.67(17) . . . . ?
N14 C3 N11 N12 1.63(19) . . . . ?
C3 N11 N12 N13 -0.8(2) . . . . ?
N11 N12 N13 N14 -0.4(2) . . . . ?
N10 C3 N14 N13 176.48(16) . . . . ?
N11 C3 N14 N13 -1.90(19) . . . . ?
N10 C3 N14 C4 -3.9(3) . . . . ?
N11 C3 N14 C4 177.70(15) . . . . ?
N12 N13 N14 C3 1.36(18) . . . . ?
N12 N13 N14 C4 -178.26(15) . . . . ?
N18 C4 N14 C3 19.4(3) . . . . ?
N15 C4 N14 C3 -160.43(17) . . . . ?
N18 C4 N14 N13 -161.10(16) . . . . ?
N15 C4 N14 N13 19.1(3) . . . . ?
N18 C4 N15 N16 0.8(2) . . . . ?
N14 C4 N15 N16 -179.43(16) . . . . ?
C4 N15 N16 N17 -1.0(2) . . . . ?
N15 N16 N17 N18 1.0(2) . . . . ?
N15 C4 N18 N17 -0.2(2) . . . . ?
N14 C4 N18 N17 180.00(15) . . . . ?
N16 N17 N18 C4 -0.5(2) . . . . ?

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
N24 H24B N17 0.89 2.51 3.175(2) 131.6 2_576 yes
N24 H24A N18 0.89 2.31 3.102(2) 148.1 . yes
N24 H24A N17 0.89 2.35 3.222(2) 165.7 . yes
N23 H23C N19 0.89 2.06 2.901(2) 156.7 2_666 yes
N23 H23C N11 0.89 2.63 3.094(2) 113.5 2_666 yes
N23 H23B N8 0.89 1.99 2.842(2) 158.9 . yes
N23 H23A N9 0.89 2.66 3.141(2) 115.1 2_666 yes
N23 H23A N1 0.89 2.16 3.012(2) 160.1 2_666 yes
N22 H22C N24 0.89 2.03 2.919(2) 177.2 2_566 yes
N22 H22B N3 0.89 2.63 3.307(2) 133.4 2_656 yes
N22 H22B N2 0.89 2.06 2.918(2) 161.3 2_656 yes
N22 H22A N9 0.89 2.03 2.910(2) 169.4 . yes
N21 H21B N11 0.89 2.41 3.218(2) 151.3 . yes
N21 H21A N3 0.89 2.59 3.238(2) 130.3 2_656 yes
N20 H20C N21 0.89 2.11 2.940(2) 155.0 1_655 yes
N20 H20C N13 0.89 2.66 3.088(2) 110.6 2_765 yes
N20 H20B N4 0.89 1.94 2.831(2) 176.7 1_654 yes
N20 H20A N12 0.89 2.11 2.944(2) 156.4 . yes
N20 H20A N11 0.89 2.68 3.306(2) 128.0 . yes
N19 H19B N15 0.89 2.34 3.190(2) 159.7 2_665 yes
N19 H19A N16 0.89 2.18 3.055(2) 168.0 1_645 yes
N10 H10 N18 0.86 2.23 2.828(2) 127.0 . yes

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.080



