# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_mo_d8v22119_0m
_database_code_depnum_ccdc_archive 'CCDC 2256906'
loop_
_audit_author_name
_audit_author_address
'pinxu Zhao'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-04-17 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 N8 O6'
_chemical_formula_weight         252.17

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

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

_cell_length_a                   13.0318(13)
_cell_length_b                   7.7973(8)
_cell_length_c                   9.8712(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.032(3)
_cell_angle_gamma                90
_cell_volume                     964.03(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    3925
_cell_measurement_theta_min      6.155
_cell_measurement_theta_max      54.979

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            4147
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.077
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1852
_reflns_number_gt                1805
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.960
_reflns_Friedel_fraction_max     0.955
_reflns_Friedel_fraction_full    0.958

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1368P)²+1.9889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 852 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.4(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1852
_refine_ls_number_parameters     186
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.1944
_refine_ls_wR_factor_gt          0.1912
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002

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
O1 O 0.6943(5) 0.5934(9) 0.9166(6) 0.0526(17) Uani 1 1 d . . . . .
O2 O 0.6472(5) 0.5300(6) 0.6945(6) 0.0417(13) Uani 1 1 d . . . . .
O3 O 0.5990(3) 0.8311(6) 0.5270(5) 0.0302(11) Uani 1 1 d . . . . .
O4 O 0.5096(4) 0.7284(7) 0.3223(5) 0.0374(12) Uani 1 1 d . . . . .
O5 O 0.3233(5) 0.6040(8) 0.3077(5) 0.0492(15) Uani 1 1 d . . . . .
O6 O 0.3062(4) 0.5309(6) 0.5125(5) 0.0388(13) Uani 1 1 d . . . . .
N1 N 0.3818(4) 0.8222(7) 0.7103(5) 0.0218(10) Uani 1 1 d . . . . .
N2 N 0.4166(5) 0.8263(8) 0.8504(6) 0.0317(12) Uani 1 1 d . . . . .
N3 N 0.5082(5) 0.7501(8) 0.8990(6) 0.0345(14) Uani 1 1 d . . . . .
N4 N 0.6307(4) 0.6023(7) 0.7992(5) 0.0252(11) Uani 1 1 d . . . . .
N5 N 0.5177(4) 0.7564(7) 0.4498(5) 0.0252(11) Uani 1 1 d . . . . .
N6 N 0.3531(4) 0.6072(6) 0.4393(5) 0.0202(10) Uani 1 1 d . . . . .
C1 C 0.5359(5) 0.6928(8) 0.7803(7) 0.0273(13) Uani 1 1 d . . . . .
C2 C 0.4554(5) 0.7334(7) 0.6621(6) 0.0236(12) Uani 1 1 d . . . . .
C3 C 0.4437(5) 0.7035(8) 0.5124(7) 0.0248(12) Uani 1 1 d . . . . .
N7 N 0.6611(4) 0.1622(7) 0.6705(6) 0.0250(11) Uani 1 1 d D . . . .
N8 N 0.3220(4) 0.8326(6) 0.0833(6) 0.0242(11) Uani 1 1 d D . . . .
H8A H 0.354(5) 0.771(7) 0.150(5) 0.013(15) Uiso 1 1 d D . . . .
H7A H 0.625(7) 0.160(11) 0.730(8) 0.04(2) Uiso 1 1 d D . . . .
H8B H 0.259(3) 0.801(11) 0.051(9) 0.04(2) Uiso 1 1 d D . . . .
H7B H 0.683(8) 0.061(5) 0.666(11) 0.06(3) Uiso 1 1 d D . . . .
H8C H 0.345(9) 0.806(15) 0.014(8) 0.06(3) Uiso 1 1 d D . . . .
H8D H 0.321(7) 0.937(5) 0.107(8) 0.028(18) Uiso 1 1 d D . . . .
H7C H 0.714(5) 0.226(10) 0.676(12) 0.06(3) Uiso 1 1 d D . . . .
H7D H 0.615(7) 0.176(13) 0.593(6) 0.05(3) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.226(7) . ?
O2 N4 1.247(8) . ?
O3 N5 1.263(7) . ?
O4 N5 1.253(7) . ?
O5 N6 1.248(7) . ?
O6 N6 1.223(7) . ?
N1 N2 1.331(7) . ?
N1 C2 1.370(8) . ?
N2 N3 1.300(8) . ?
N3 C1 1.391(9) . ?
N4 C1 1.390(8) . ?
N5 C3 1.345(8) . ?
N6 C3 1.418(7) . ?
C1 C2 1.374(9) . ?
C2 C3 1.462(8) . ?
N7 H7A 0.84(3) . ?
N7 H7B 0.84(3) . ?
N7 H7C 0.84(3) . ?
N7 H7D 0.84(3) . ?
N8 H8A 0.83(3) . ?
N8 H8B 0.83(3) . ?
N8 H8C 0.84(3) . ?
N8 H8D 0.85(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
N2 N1 C2 107.6(5) . . ?
N3 N2 N1 112.8(5) . . ?
N2 N3 C1 105.1(5) . . ?
O1 N4 O2 122.1(6) . . ?
O1 N4 C1 119.9(6) . . ?
O2 N4 C1 117.9(6) . . ?
O4 N5 O3 120.7(5) . . ?
O4 N5 C3 122.4(5) . . ?
O3 N5 C3 116.9(5) . . ?
O6 N6 O5 122.8(5) . . ?
O6 N6 C3 116.0(5) . . ?
O5 N6 C3 121.1(5) . . ?
C2 C1 N3 109.1(5) . . ?
C2 C1 N4 132.3(6) . . ?
N3 C1 N4 118.5(6) . . ?
N1 C2 C1 105.3(5) . . ?
N1 C2 C3 123.0(5) . . ?
C1 C2 C3 131.6(6) . . ?
N5 C3 N6 122.0(6) . . ?
N5 C3 C2 121.8(5) . . ?
N6 C3 C2 116.0(5) . . ?
H7A N7 H7B 106(9) . . ?
H7A N7 H7C 125(10) . . ?
H7B N7 H7C 105(5) . . ?
H7A N7 H7D 104(10) . . ?
H7B N7 H7D 104(10) . . ?
H7C N7 H7D 111(10) . . ?
H8A N8 H8B 111(8) . . ?
H8A N8 H8C 106(10) . . ?
H8B N8 H8C 99(10) . . ?
H8A N8 H8D 112(7) . . ?
H8B N8 H8D 107(8) . . ?
H8C N8 H8D 120(10) . . ?

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
C2 N1 N2 N3 1.2(7) . . . . ?
N1 N2 N3 C1 0.5(8) . . . . ?
N2 N3 C1 C2 -2.0(8) . . . . ?
N2 N3 C1 N4 -178.9(5) . . . . ?
O1 N4 C1 C2 174.8(7) . . . . ?
O2 N4 C1 C2 -6.4(10) . . . . ?
O1 N4 C1 N3 -9.3(9) . . . . ?
O2 N4 C1 N3 169.6(6) . . . . ?
N2 N1 C2 C1 -2.4(6) . . . . ?
N2 N1 C2 C3 -179.8(5) . . . . ?
N3 C1 C2 N1 2.7(7) . . . . ?
N4 C1 C2 N1 179.0(6) . . . . ?
N3 C1 C2 C3 179.9(6) . . . . ?
N4 C1 C2 C3 -3.9(11) . . . . ?
O4 N5 C3 N6 2.1(9) . . . . ?
O3 N5 C3 N6 -175.2(5) . . . . ?
O4 N5 C3 C2 178.5(5) . . . . ?
O3 N5 C3 C2 1.1(8) . . . . ?
O6 N6 C3 N5 162.6(6) . . . . ?
O5 N6 C3 N5 -18.4(9) . . . . ?
O6 N6 C3 C2 -14.0(7) . . . . ?
O5 N6 C3 C2 165.0(6) . . . . ?
N1 C2 C3 N5 121.9(7) . . . . ?
C1 C2 C3 N5 -54.9(9) . . . . ?
N1 C2 C3 N6 -61.6(7) . . . . ?
C1 C2 C3 N6 121.7(7) . . . . ?

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
N7 H7D N3 0.84(3) 2.11(4) 2.945(8) 171(10) 2_564
N7 H7C N1 0.84(3) 2.24(4) 3.059(7) 163(9) 3_545
N8 H8D N1 0.85(3) 2.18(4) 2.980(7) 157(8) 2_574
N8 H8C N3 0.84(3) 2.71(6) 3.471(8) 151(10) 1_554
N8 H8C N2 0.84(3) 2.09(5) 2.894(8) 161(11) 1_554
N7 H7B O6 0.84(3) 2.50(9) 2.947(7) 114(7) 3_545
N7 H7B O5 0.84(3) 2.35(8) 3.004(8) 135(9) 4
N7 H7B O3 0.84(3) 2.34(8) 2.949(7) 129(9) 1_545
N8 H8B O3 0.83(3) 2.28(4) 3.081(7) 162(9) 4_464
N7 H7A O4 0.84(3) 2.15(5) 2.916(8) 151(9) 2_565
N8 H8A O5 0.83(3) 2.15(5) 2.840(8) 140(6) .
N8 H8A O4 0.83(3) 2.28(5) 3.003(8) 146(6) .
N8 H8A O4 0.83(3) 2.28(5) 3.003(8) 146(6) .
N8 H8A O5 0.83(3) 2.15(5) 2.840(8) 140(6) .
N7 H7A O4 0.84(3) 2.15(5) 2.916(8) 151(9) 2_565
N8 H8B O3 0.83(3) 2.28(4) 3.081(7) 162(9) 4_464
N7 H7B O3 0.84(3) 2.34(8) 2.949(7) 129(9) 1_545
N7 H7B O5 0.84(3) 2.35(8) 3.004(8) 135(9) 4
N7 H7B O6 0.84(3) 2.50(9) 2.947(7) 114(7) 3_545
N8 H8C N2 0.84(3) 2.09(5) 2.894(8) 161(11) 1_554
N8 H8C N3 0.84(3) 2.71(6) 3.471(8) 151(10) 1_554
N8 H8D N1 0.85(3) 2.18(4) 2.980(7) 157(8) 2_574
N7 H7C N1 0.84(3) 2.24(4) 3.059(7) 163(9) 3_545
N7 H7D N3 0.84(3) 2.11(4) 2.945(8) 171(10) 2_564

_refine_diff_density_max         1.009
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.102

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v22023
_database_code_depnum_ccdc_archive 'CCDC 2256907'
loop_
_audit_author_name
_audit_author_address
'pinxu Zhao'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-04-17 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H K N6 O6'
_chemical_formula_weight         256.20

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'
K K 0.2009 0.2494 '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                   8.7186(2)
_cell_length_b                   11.5384(3)
_cell_length_c                   8.1605(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.9940(10)
_cell_angle_gamma                90
_cell_volume                     818.94(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    6679
_cell_measurement_theta_min      4.683
_cell_measurement_theta_max      54.976

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.078
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            7864
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.062
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             1579
_reflns_number_gt                1522
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0322P)²+0.3604P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1579
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0602
_refine_ls_wR_factor_gt          0.0596
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.27519(3) 0.09167(2) 0.40079(4) 0.02511(14) Uani 1 1 d . . . . .
O6 O 0.56984(10) 0.46285(8) 0.34962(11) 0.0237(2) Uani 1 1 d . . . . .
O3 O 0.77675(11) 0.15430(8) 0.61697(12) 0.0268(2) Uani 1 1 d . . . . .
O4 O 0.58674(11) 0.11780(8) 0.43942(13) 0.0279(2) Uani 1 1 d . . . . .
O2 O 1.00135(11) 0.23837(9) 0.42591(12) 0.0301(3) Uani 1 1 d . . . . .
O5 O 0.45684(12) 0.29735(9) 0.29799(13) 0.0326(3) Uani 1 1 d . . . . .
O1 O 1.18233(11) 0.30914(9) 0.59110(13) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.73993(13) 0.46999(9) 0.66547(14) 0.0213(3) Uani 1 1 d . . . . .
N6 N 0.56081(12) 0.35410(9) 0.37198(13) 0.0203(2) Uani 1 1 d . . . . .
N3 N 0.98444(13) 0.46381(9) 0.70939(13) 0.0216(3) Uani 1 1 d . . . . .
N5 N 0.67654(12) 0.18776(9) 0.51221(13) 0.0195(2) Uani 1 1 d . . . . .
N4 N 1.04764(12) 0.30404(9) 0.53645(13) 0.0210(2) Uani 1 1 d . . . . .
N2 N 0.86119(13) 0.52041(10) 0.74760(14) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.93764(14) 0.37959(10) 0.60280(15) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.78046(14) 0.38065(11) 0.57281(15) 0.0176(3) Uani 1 1 d . . . . .
C3 C 0.67059(14) 0.30656(11) 0.48095(15) 0.0187(3) Uani 1 1 d . . . . .
H1 H 0.645(2) 0.4902(15) 0.674(2) 0.031(4) Uiso 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 O4 2.7293(10) . ?
K1 O1 2.8403(11) 4_465 ?
K1 O3 2.8762(10) 3_656 ?
K1 O6 2.9318(10) 2_645 ?
K1 O2 2.9454(10) 1_455 ?
K1 N3 2.9535(11) 4_465 ?
K1 O4 2.9618(10) 3_656 ?
K1 O5 3.0049(11) . ?
K1 O1 3.0884(11) 1_455 ?
K1 N2 3.2861(12) 2_646 ?
K1 N5 3.3219(11) 3_656 ?
K1 N4 3.3870(11) 1_455 ?
O6 N6 1.2713(14) . ?
O6 K1 2.9318(10) 2_655 ?
O3 N5 1.2407(14) . ?
O3 K1 2.8761(10) 3_656 ?
O4 N5 1.2461(14) . ?
O4 K1 2.9618(10) 3_656 ?
O2 N4 1.2247(14) . ?
O2 K1 2.9454(10) 1_655 ?
O5 N6 1.2405(14) . ?
O1 N4 1.2282(15) . ?
O1 K1 2.8402(11) 4_666 ?
O1 K1 3.0885(11) 1_655 ?
N1 C2 1.3403(17) . ?
N1 N2 1.3441(16) . ?
N1 H1 0.865(19) . ?
N6 C3 1.3745(16) . ?
N3 N2 1.3134(16) . ?
N3 C1 1.3484(16) . ?
N3 K1 2.9535(11) 4_666 ?
N5 C3 1.3946(16) . ?
N5 K1 3.3219(11) 3_656 ?
N4 C1 1.4300(16) . ?
N4 K1 3.3870(11) 1_655 ?
N2 K1 3.2861(12) 2_656 ?
C1 C2 1.3753(18) . ?
C2 C3 1.4527(17) . ?

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
O4 K1 O1 106.14(3) . 4_465 ?
O4 K1 O3 105.47(3) . 3_656 ?
O1 K1 O3 108.58(3) 4_465 3_656 ?
O4 K1 O6 68.48(3) . 2_645 ?
O1 K1 O6 72.59(3) 4_465 2_645 ?
O3 K1 O6 62.82(3) 3_656 2_645 ?
O4 K1 O2 137.18(3) . 1_455 ?
O1 K1 O2 69.40(3) 4_465 1_455 ?
O3 K1 O2 116.43(3) 3_656 1_455 ?
O6 K1 O2 139.03(3) 2_645 1_455 ?
O4 K1 N3 153.58(3) . 4_465 ?
O1 K1 N3 55.66(3) 4_465 4_465 ?
O3 K1 N3 68.48(3) 3_656 4_465 ?
O6 K1 N3 86.66(3) 2_645 4_465 ?
O2 K1 N3 59.43(3) 1_455 4_465 ?
O4 K1 O4 70.64(3) . 3_656 ?
O1 K1 O4 143.37(3) 4_465 3_656 ?
O3 K1 O4 43.50(3) 3_656 3_656 ?
O6 K1 O4 72.56(3) 2_645 3_656 ?
O2 K1 O4 138.15(3) 1_455 3_656 ?
N3 K1 O4 111.32(3) 4_465 3_656 ?
O4 K1 O5 53.51(3) . . ?
O1 K1 O5 63.67(3) 4_465 . ?
O3 K1 O5 148.15(3) 3_656 . ?
O6 K1 O5 85.89(3) 2_645 . ?
O2 K1 O5 90.64(3) 1_455 . ?
N3 K1 O5 118.24(3) 4_465 . ?
O4 K1 O5 124.15(3) 3_656 . ?
O4 K1 O1 98.39(3) . 1_455 ?
O1 K1 O1 92.957(17) 4_465 1_455 ?
O3 K1 O1 141.37(3) 3_656 1_455 ?
O6 K1 O1 155.79(3) 2_645 1_455 ?
O2 K1 O1 41.92(3) 1_455 1_455 ?
N3 K1 O1 101.34(3) 4_465 1_455 ?
O4 K1 O1 123.66(3) 3_656 1_455 ?
O5 K1 O1 70.15(3) . 1_455 ?
O4 K1 N2 110.15(3) . 2_646 ?
O1 K1 N2 141.23(3) 4_465 2_646 ?
O3 K1 N2 74.44(3) 3_656 2_646 ?
O6 K1 N2 133.96(3) 2_645 2_646 ?
O2 K1 N2 74.85(3) 1_455 2_646 ?
N3 K1 N2 93.33(3) 4_465 2_646 ?
O4 K1 N2 64.66(3) 3_656 2_646 ?
O5 K1 N2 132.16(3) . 2_646 ?
O1 K1 N2 68.94(3) 1_455 2_646 ?
O4 K1 N5 88.41(3) . 3_656 ?
O1 K1 N5 127.25(3) 4_465 3_656 ?
O3 K1 N5 21.59(3) 3_656 3_656 ?
O6 K1 N5 66.37(3) 2_645 3_656 ?
O2 K1 N5 129.36(3) 1_455 3_656 ?
N3 K1 N5 89.65(3) 4_465 3_656 ?
O4 K1 N5 21.92(3) 3_656 3_656 ?
O5 K1 N5 139.89(3) . 3_656 ?
O1 K1 N5 135.63(3) 1_455 3_656 ?
N2 K1 N5 67.59(3) 2_646 3_656 ?
O4 K1 N4 118.90(3) . 1_455 ?
O1 K1 N4 82.08(3) 4_465 1_455 ?
O3 K1 N4 129.54(3) 3_656 1_455 ?
O6 K1 N4 154.62(3) 2_645 1_455 ?
O2 K1 N4 20.84(3) 1_455 1_455 ?
N3 K1 N4 80.15(3) 4_465 1_455 ?
O4 K1 N4 132.52(3) 3_656 1_455 ?
O5 K1 N4 81.49(3) . 1_455 ?
O1 K1 N4 21.23(3) 1_455 1_455 ?
N2 K1 N4 68.89(3) 2_646 1_455 ?
N5 K1 N4 134.49(3) 3_656 1_455 ?
N6 O6 K1 129.54(7) . 2_655 ?
N5 O3 K1 99.88(7) . 3_656 ?
N5 O4 K1 135.54(8) . . ?
N5 O4 K1 95.52(7) . 3_656 ?
K1 O4 K1 109.36(3) . 3_656 ?
N4 O2 K1 100.35(7) . 1_655 ?
N6 O5 K1 131.49(8) . . ?
N4 O1 K1 123.26(8) . 4_666 ?
N4 O1 K1 93.21(7) . 1_655 ?
K1 O1 K1 134.94(4) 4_666 1_655 ?
C2 N1 N2 112.65(11) . . ?
C2 N1 H1 122.8(12) . . ?
N2 N1 H1 124.5(12) . . ?
O5 N6 O6 120.11(10) . . ?
O5 N6 C3 123.82(11) . . ?
O6 N6 C3 116.07(10) . . ?
N2 N3 C1 107.20(10) . . ?
N2 N3 K1 131.95(8) . 4_666 ?
C1 N3 K1 113.26(8) . 4_666 ?
O3 N5 O4 121.05(11) . . ?
O3 N5 C3 116.57(10) . . ?
O4 N5 C3 122.38(11) . . ?
O3 N5 K1 58.53(6) . 3_656 ?
O4 N5 K1 62.56(6) . 3_656 ?
C3 N5 K1 174.64(8) . 3_656 ?
O2 N4 O1 123.70(11) . . ?
O2 N4 C1 117.43(11) . . ?
O1 N4 C1 118.86(11) . . ?
O2 N4 K1 58.81(6) . 1_655 ?
O1 N4 K1 65.57(7) . 1_655 ?
C1 N4 K1 171.21(8) . 1_655 ?
N3 N2 N1 107.13(10) . . ?
N3 N2 K1 133.12(8) . 2_656 ?
N1 N2 K1 102.93(8) . 2_656 ?
N3 C1 C2 111.18(11) . . ?
N3 C1 N4 120.19(11) . . ?
C2 C1 N4 128.63(11) . . ?
N1 C2 C1 101.83(11) . . ?
N1 C2 C3 123.61(11) . . ?
C1 C2 C3 134.40(12) . . ?
N6 C3 N5 121.73(11) . . ?
N6 C3 C2 120.23(11) . . ?
N5 C3 C2 117.99(11) . . ?

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 O5 N6 O6 -144.33(9) . . . . ?
K1 O5 N6 C3 35.33(17) . . . . ?
K1 O6 N6 O5 -87.05(13) 2_655 . . . ?
K1 O6 N6 C3 93.27(11) 2_655 . . . ?
K1 O3 N5 O4 2.38(12) 3_656 . . . ?
K1 O3 N5 C3 -177.51(9) 3_656 . . . ?
K1 O4 N5 O3 122.74(11) . . . . ?
K1 O4 N5 O3 -2.29(12) 3_656 . . . ?
K1 O4 N5 C3 -57.38(17) . . . . ?
K1 O4 N5 C3 177.59(10) 3_656 . . . ?
K1 O4 N5 K1 125.03(11) . . . 3_656 ?
K1 O2 N4 O1 9.99(14) 1_655 . . . ?
K1 O2 N4 C1 -170.88(9) 1_655 . . . ?
K1 O1 N4 O2 -161.37(9) 4_666 . . . ?
K1 O1 N4 O2 -9.38(13) 1_655 . . . ?
K1 O1 N4 C1 19.51(15) 4_666 . . . ?
K1 O1 N4 C1 171.50(9) 1_655 . . . ?
K1 O1 N4 K1 -151.99(9) 4_666 . . 1_655 ?
C1 N3 N2 N1 0.52(13) . . . . ?
K1 N3 N2 N1 -146.00(9) 4_666 . . . ?
C1 N3 N2 K1 128.06(10) . . . 2_656 ?
K1 N3 N2 K1 -18.46(16) 4_666 . . 2_656 ?
C2 N1 N2 N3 -0.09(14) . . . . ?
C2 N1 N2 K1 -143.66(9) . . . 2_656 ?
N2 N3 C1 C2 -0.78(14) . . . . ?
K1 N3 C1 C2 152.70(8) 4_666 . . . ?
N2 N3 C1 N4 178.95(11) . . . . ?
K1 N3 C1 N4 -27.57(13) 4_666 . . . ?
O2 N4 C1 N3 -171.51(11) . . . . ?
O1 N4 C1 N3 7.67(18) . . . . ?
O2 N4 C1 C2 8.17(19) . . . . ?
O1 N4 C1 C2 -172.65(12) . . . . ?
N2 N1 C2 C1 -0.36(14) . . . . ?
N2 N1 C2 C3 175.59(11) . . . . ?
N3 C1 C2 N1 0.69(14) . . . . ?
N4 C1 C2 N1 -179.02(12) . . . . ?
N3 C1 C2 C3 -174.59(13) . . . . ?
N4 C1 C2 C3 5.7(2) . . . . ?
O5 N6 C3 N5 2.50(19) . . . . ?
O6 N6 C3 N5 -177.83(11) . . . . ?
O5 N6 C3 C2 -174.77(12) . . . . ?
O6 N6 C3 C2 4.90(16) . . . . ?
O3 N5 C3 N6 -177.53(11) . . . . ?
O4 N5 C3 N6 2.58(18) . . . . ?
O3 N5 C3 C2 -0.21(17) . . . . ?
O4 N5 C3 C2 179.91(11) . . . . ?
N1 C2 C3 N6 54.33(17) . . . . ?
C1 C2 C3 N6 -131.22(15) . . . . ?
N1 C2 C3 N5 -123.04(13) . . . . ?
C1 C2 C3 N5 51.4(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
N1 H1 N6 0.865(19) 2.549(18) 3.3131(15) 147.7(16) 3_666
N1 H1 O5 0.865(19) 2.623(18) 3.2110(15) 126.2(15) 3_666
N1 H1 O6 0.865(19) 1.948(19) 2.8042(15) 169.9(17) 3_666
N1 H1 O6 0.865(19) 1.948(19) 2.8042(15) 169.9(17) 3_666
N1 H1 O5 0.865(19) 2.623(18) 3.2110(15) 126.2(15) 3_666
N1 H1 N6 0.865(19) 2.549(18) 3.3131(15) 147.7(16) 3_666

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v22495
_database_code_depnum_ccdc_archive 'CCDC 2256912'
loop_
_audit_author_name
_audit_author_address
'pinxu Zhao'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-04-17 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H14 N14 O6'
_chemical_formula_weight         366.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   17.215(2)
_cell_length_b                   6.5819(7)
_cell_length_c                   13.6351(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.543(4)
_cell_angle_gamma                90
_cell_volume                     1473.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    7091
_cell_measurement_theta_min      4.963
_cell_measurement_theta_max      54.750

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5239
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            19333
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.003
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2886
_reflns_number_gt                2343
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0513P)²+0.7444P] 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     SHELXL
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2886
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.025
_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
O1 O 0.28164(9) 0.0401(2) 0.21319(12) 0.0445(4) Uani 1 1 d . . . . .
O2 O 0.18396(8) 0.1695(2) 0.26281(12) 0.0448(4) Uani 1 1 d . . . . .
O3 O 0.26131(9) 0.7044(2) 0.35578(14) 0.0501(4) Uani 1 1 d . . . . .
O4 O 0.15609(10) 0.7475(2) 0.40823(16) 0.0598(5) Uani 1 1 d . . . . .
O5 O 0.10855(8) 0.4330(2) 0.48536(12) 0.0424(4) Uani 1 1 d . . . . .
O6 O 0.19391(9) 0.1802(2) 0.52185(12) 0.0431(4) Uani 1 1 d . . . . .
N1 N 0.37368(10) 0.3599(3) 0.51137(12) 0.0348(4) Uani 1 1 d . . . . .
N2 N 0.42734(10) 0.2390(3) 0.48416(13) 0.0365(4) Uani 1 1 d . . . . .
N3 N 0.39159(9) 0.1434(2) 0.39654(12) 0.0313(4) Uani 1 1 d . . . . .
N4 N 0.25659(10) 0.1328(2) 0.27553(13) 0.0321(4) Uani 1 1 d . . . . .
N5 N 0.21340(10) 0.6396(3) 0.40097(14) 0.0364(4) Uani 1 1 d . . . . .
N6 N 0.17509(10) 0.3545(2) 0.48522(13) 0.0326(4) Uani 1 1 d . . . . .
C1 C 0.31368(10) 0.2040(3) 0.36846(14) 0.0268(4) Uani 1 1 d . . . . .
C2 C 0.30142(11) 0.3389(3) 0.43945(14) 0.0270(4) Uani 1 1 d . . . . .
C3 C 0.22880(11) 0.4488(3) 0.44394(14) 0.0289(4) Uani 1 1 d . . . . .
N7 N 0.46095(10) 0.4277(2) 0.72610(13) 0.0341(4) Uani 1 1 d . . . . .
H7A H 0.4303 0.4197 0.6625 0.041 Uiso 1 1 calc R U . . .
H7B H 0.4391 0.4504 0.7749 0.041 Uiso 1 1 calc R U . . .
N8 N 0.57493(10) 0.3709(3) 0.67608(13) 0.0356(4) Uani 1 1 d . . . . .
H8A H 0.5452 0.3625 0.6121 0.043 Uiso 1 1 calc R U . . .
H8B H 0.6275 0.3565 0.6922 0.043 Uiso 1 1 calc DR U . . .
N9 N 0.58561(11) 0.4198(3) 0.84637(14) 0.0416(4) Uani 1 1 d . . . . .
H9 H 0.5630 0.4423 0.8944 0.050 Uiso 1 1 calc R U . . .
N10 N 0.67006(13) 0.3983(4) 0.87064(19) 0.0715(7) Uani 1 1 d . . . . .
H10A H 0.6928 0.4287 0.9349 0.086 Uiso 1 1 d R U . . .
H10B H 0.6819 0.2736 0.8602 0.086 Uiso 1 1 d DR U . . .
C4 C 0.54039(11) 0.4054(3) 0.74851(15) 0.0285(4) Uani 1 1 d . . . . .
N11 N -0.10782(11) 1.2498(3) 0.34682(16) 0.0459(5) Uani 1 1 d . . . . .
H11A H -0.1525 1.2660 0.2967 0.055 Uiso 1 1 d R U . . .
H11B H -0.1116 1.3180 0.3996 0.055 Uiso 1 1 d R U . . .
N12 N -0.09499(10) 1.0436(2) 0.37241(14) 0.0366(4) Uani 1 1 d . . . . .
H12 H -0.1313 0.9740 0.3908 0.044 Uiso 1 1 calc R U . . .
N13 N 0.02476(11) 1.0590(3) 0.33305(16) 0.0478(5) Uani 1 1 d . . . . .
H13A H 0.0692 1.0014 0.3291 0.057 Uiso 1 1 calc R U . . .
H13B H 0.0144 1.1846 0.3137 0.057 Uiso 1 1 calc R U . . .
N14 N -0.01254(10) 0.7659(3) 0.39791(15) 0.0414(5) Uani 1 1 d . . . . .
H14A H 0.0316 0.7056 0.3946 0.050 Uiso 1 1 calc R U . . .
H14B H -0.0473 0.7003 0.4209 0.050 Uiso 1 1 calc R U . . .
C5 C -0.02665(11) 0.9563(3) 0.36813(14) 0.0299(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


O1 N4 1.226(2) . ?
O2 N4 1.233(2) . ?
O3 N5 1.244(2) . ?
O4 N5 1.243(2) . ?
O5 N6 1.257(2) . ?
O6 N6 1.254(2) . ?
N1 C2 1.339(2) . ?
N1 N2 1.353(2) . ?
N2 N3 1.327(2) . ?
N3 C1 1.340(2) . ?
N4 C1 1.428(2) . ?
N5 C3 1.378(2) . ?
N6 C3 1.368(2) . ?
C1 C2 1.376(3) . ?
C2 C3 1.461(2) . ?
N7 C4 1.316(2) . ?
N7 H7A 0.8700 . ?
N7 H7B 0.8700 . ?
N8 C4 1.317(2) . ?
N8 H8A 0.8700 . ?
N8 H8B 0.8700 . ?
N9 C4 1.330(3) . ?
N9 N10 1.397(3) . ?
N9 H9 0.8700 . ?
N10 H10A 0.8685 . ?
N10 H10B 0.8678 . ?
N11 N12 1.402(2) . ?
N11 H11A 0.8678 . ?
N11 H11B 0.8673 . ?
N12 C5 1.326(2) . ?
N12 H12 0.8700 . ?
N13 C5 1.313(3) . ?
N13 H13A 0.8700 . ?
N13 H13B 0.8700 . ?
N14 C5 1.317(3) . ?
N14 H14A 0.8700 . ?
N14 H14B 0.8700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 O4 H14A 136.6 . . ?
C2 N1 N2 107.39(15) . . ?
C2 N1 H7A 144.8 . . ?
N2 N1 H7A 103.5 . . ?
N3 N2 N1 110.87(15) . . ?
N2 N3 C1 105.58(15) . . ?
O1 N4 O2 123.62(17) . . ?
O1 N4 C1 119.13(16) . . ?
O2 N4 C1 117.25(16) . . ?
O4 N5 O3 120.29(17) . . ?
O4 N5 C3 122.85(16) . . ?
O3 N5 C3 116.83(15) . . ?
O6 N6 O5 120.11(15) . . ?
O6 N6 C3 116.97(15) . . ?
O5 N6 C3 122.90(16) . . ?
N3 C1 C2 110.11(16) . . ?
N3 C1 N4 121.17(16) . . ?
C2 C1 N4 128.71(16) . . ?
N1 C2 C1 106.03(15) . . ?
N1 C2 C3 122.40(17) . . ?
C1 C2 C3 131.56(17) . . ?
N6 C3 N5 121.44(16) . . ?
N6 C3 C2 119.05(16) . . ?
N5 C3 C2 119.39(16) . . ?
C4 N7 H7A 120.0 . . ?
C4 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C4 N8 H8A 120.0 . . ?
C4 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C4 N9 N10 118.88(19) . . ?
C4 N9 H9 120.6 . . ?
N10 N9 H9 120.6 . . ?
N9 N10 H10A 109.7 . . ?
N9 N10 H10B 109.6 . . ?
H10A N10 H10B 109.1 . . ?
N7 C4 N8 121.15(18) . . ?
N7 C4 N9 118.55(18) . . ?
N8 C4 N9 120.29(18) . . ?
N12 N11 H11A 110.5 . . ?
N12 N11 H11B 109.9 . . ?
H11A N11 H11B 108.6 . . ?
C5 N12 N11 118.93(16) . . ?
C5 N12 H12 120.5 . . ?
N11 N12 H12 120.5 . . ?
C5 N13 H13A 120.0 . . ?
C5 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C5 N14 H14A 120.0 . . ?
C5 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
N13 C5 N14 121.36(18) . . ?
N13 C5 N12 119.81(18) . . ?
N14 C5 N12 118.83(17) . . ?

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
C2 N1 N2 N3 0.6(2) . . . . ?
H7A N1 N2 N3 163.6 . . . . ?
N1 N2 N3 C1 -0.5(2) . . . . ?
H14A O4 N5 O3 138.0 . . . . ?
H14A O4 N5 C3 -44.0 . . . . ?
N2 N3 C1 C2 0.2(2) . . . . ?
N2 N3 C1 N4 179.07(16) . . . . ?
O1 N4 C1 N3 -11.1(3) . . . . ?
O2 N4 C1 N3 168.96(16) . . . . ?
O1 N4 C1 C2 167.55(18) . . . . ?
O2 N4 C1 C2 -12.4(3) . . . . ?
N2 N1 C2 C1 -0.5(2) . . . . ?
H7A N1 C2 C1 -150.8 . . . . ?
N2 N1 C2 C3 -179.77(16) . . . . ?
H7A N1 C2 C3 29.9 . . . . ?
N3 C1 C2 N1 0.2(2) . . . . ?
N4 C1 C2 N1 -178.59(17) . . . . ?
N3 C1 C2 C3 179.39(18) . . . . ?
N4 C1 C2 C3 0.6(3) . . . . ?
O6 N6 C3 N5 179.43(18) . . . . ?
O5 N6 C3 N5 1.1(3) . . . . ?
O6 N6 C3 C2 3.5(3) . . . . ?
O5 N6 C3 C2 -174.88(17) . . . . ?
O4 N5 C3 N6 9.3(3) . . . . ?
O3 N5 C3 N6 -172.64(18) . . . . ?
O4 N5 C3 C2 -174.8(2) . . . . ?
O3 N5 C3 C2 3.3(3) . . . . ?
N1 C2 C3 N6 -96.2(2) . . . . ?
C1 C2 C3 N6 84.8(3) . . . . ?
N1 C2 C3 N5 87.8(2) . . . . ?
C1 C2 C3 N5 -91.3(3) . . . . ?
N10 N9 C4 N7 -179.38(19) . . . . ?
N10 N9 C4 N8 0.2(3) . . . . ?
N11 N12 C5 N13 -5.0(3) . . . . ?
N11 N12 C5 N14 176.09(19) . . . . ?

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
N14 H14B O5 0.87 2.08 2.926(2) 164.3 3_566
N14 H14A O5 0.87 2.35 3.011(2) 133.1 .
N14 H14A O4 0.87 2.11 2.866(2) 144.5 .
N13 H13A O4 0.87 2.28 2.995(2) 138.8 .
N13 H13A O2 0.87 2.65 3.247(2) 126.8 1_565
N12 H12 O6 0.87 2.09 2.937(2) 163.0 3_566
N11 H11B O5 0.87 2.26 3.100(3) 163.9 3_576
N11 H11A O3 0.87 2.38 3.210(3) 161.0 2
N10 H10B O1 0.87 2.46 3.301(3) 164.4 3_656
N10 H10A O6 0.87 2.49 3.001(3) 118.4 2_656
N9 H9 N2 0.87 2.53 3.180(2) 131.8 2_656
N8 H8B O3 0.87 2.24 3.020(2) 149.6 3_666
N8 H8A N2 0.87 2.38 3.170(2) 150.4 .
N7 H7B N3 0.87 2.15 2.953(2) 153.3 4_566
N7 H7B O1 0.87 2.59 3.046(2) 114.1 4_566
N7 H7A N2 0.87 2.69 3.407(2) 140.1 .
N7 H7A N1 0.87 2.04 2.894(2) 169.2 .
N14 H14B O5 0.87 2.08 2.926(2) 164.3 3_566
N14 H14A O5 0.87 2.35 3.011(2) 133.1 .
N14 H14A O4 0.87 2.11 2.866(2) 144.5 .
N13 H13A O4 0.87 2.28 2.995(2) 138.8 .
N13 H13A O2 0.87 2.65 3.247(2) 126.8 1_565
N12 H12 O6 0.87 2.09 2.937(2) 163.0 3_566
N11 H11B O5 0.87 2.26 3.100(3) 163.9 3_576
N11 H11A O3 0.87 2.38 3.210(3) 161.0 2
N10 H10B O1 0.87 2.46 3.301(3) 164.4 3_656
N9 H9 N2 0.87 2.53 3.180(2) 131.8 2_656
N8 H8B O3 0.87 2.24 3.020(2) 149.6 3_666
N8 H8A N2 0.87 2.38 3.170(2) 150.4 .
N7 H7B N3 0.87 2.15 2.953(2) 153.3 4_566
N7 H7B O1 0.87 2.59 3.046(2) 114.1 4_566
N7 H7A N2 0.87 2.69 3.407(2) 140.1 .
N7 H7A N1 0.87 2.04 2.894(2) 169.2 .
N14 H14B O5 0.87 2.08 2.926(2) 164.3 3_566
N14 H14A O5 0.87 2.35 3.011(2) 133.1 .
N14 H14A O4 0.87 2.11 2.866(2) 144.5 .
N13 H13A O4 0.87 2.28 2.995(2) 138.8 .
N13 H13A O2 0.87 2.65 3.247(2) 126.8 1_565
N12 H12 O6 0.87 2.09 2.937(2) 163.0 3_566
N11 H11B O5 0.87 2.26 3.100(3) 163.9 3_576
N11 H11A O3 0.87 2.38 3.210(3) 161.0 2
N9 H9 N2 0.87 2.53 3.180(2) 131.8 2_656
N8 H8B O3 0.87 2.24 3.020(2) 149.6 3_666
N8 H8A N2 0.87 2.38 3.170(2) 150.4 .
N7 H7B N3 0.87 2.15 2.953(2) 153.3 4_566
N7 H7B O1 0.87 2.59 3.046(2) 114.1 4_566
N7 H7A N2 0.87 2.69 3.407(2) 140.1 .
N7 H7A N1 0.87 2.04 2.894(2) 169.2 .
N7 H7A N1 0.87 2.04 2.894(2) 169.2 .
N7 H7A N2 0.87 2.69 3.407(2) 140.1 .
N7 H7B O1 0.87 2.59 3.046(2) 114.1 4_566
N7 H7B N3 0.87 2.15 2.953(2) 153.3 4_566
N8 H8A N2 0.87 2.38 3.170(2) 150.4 .
N8 H8B O3 0.87 2.24 3.020(2) 149.6 3_666
N9 H9 N2 0.87 2.53 3.180(2) 131.8 2_656
N11 H11A O3 0.87 2.38 3.210(3) 161.0 2
N11 H11B O5 0.87 2.26 3.100(3) 163.9 3_576
N12 H12 O6 0.87 2.09 2.937(2) 163.0 3_566
N13 H13A O2 0.87 2.65 3.247(2) 126.8 1_565
N13 H13A O4 0.87 2.28 2.995(2) 138.8 .
N14 H14A O4 0.87 2.11 2.866(2) 144.5 .
N14 H14A O5 0.87 2.35 3.011(2) 133.1 .
N14 H14B O5 0.87 2.08 2.926(2) 164.3 3_566

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v22253
_database_code_depnum_ccdc_archive 'CCDC 2256909'
loop_
_audit_author_name
_audit_author_address
'pinxu Zhao'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-04-17 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H10 N10 O6'
_chemical_formula_weight         282.21

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                   13.6418(5)
_cell_length_b                   9.7046(3)
_cell_length_c                   8.1716(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.1170(10)
_cell_angle_gamma                90
_cell_volume                     1057.72(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5454
_cell_measurement_theta_min      5.191
_cell_measurement_theta_max      54.637

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            15498
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2074
_reflns_number_gt                1715
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0321P)²+0.5697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0106(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2074
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
O1 O 0.06747(11) 1.00972(15) 0.2538(2) 0.0484(4) Uani 1 1 d . . . . .
O2 O 0.22515(10) 1.05937(14) 0.32888(18) 0.0382(4) Uani 1 1 d . . . . .
O3 O 0.26848(10) 1.01539(15) 0.68830(17) 0.0368(4) Uani 1 1 d . . . . .
O4 O 0.43036(9) 1.03850(12) 0.74139(15) 0.0293(3) Uani 1 1 d . . . . .
O5 O 0.52808(9) 0.85911(14) 0.60455(16) 0.0314(3) Uani 1 1 d . . . . .
O6 O 0.43813(10) 0.71086(15) 0.44143(18) 0.0395(4) Uani 1 1 d . . . . .
N1 N 0.10527(11) 0.74549(16) 0.3531(2) 0.0301(4) Uani 1 1 d . . . . .
N2 N 0.14776(11) 0.63455(16) 0.4312(2) 0.0323(4) Uani 1 1 d . . . . .
N3 N 0.24156(11) 0.66229(15) 0.51712(19) 0.0287(4) Uani 1 1 d . . . . .
N4 N 0.15442(11) 0.97925(16) 0.31970(19) 0.0286(4) Uani 1 1 d . . . . .
N5 N 0.44455(10) 0.81116(15) 0.53933(18) 0.0238(3) Uani 1 1 d . . . . .
N6 N 0.35256(11) 0.97544(15) 0.66905(17) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.17453(13) 0.84525(17) 0.3880(2) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.26078(12) 0.79526(17) 0.4912(2) 0.0225(4) Uani 1 1 d . . . . .
C3 C 0.35472(12) 0.86330(17) 0.5671(2) 0.0224(4) Uani 1 1 d . . . . .
N7 N 0.62217(12) 0.93740(16) 0.9326(2) 0.0267(4) Uani 1 1 d . . . . .
N8 N 0.67725(13) 0.80944(17) 0.9438(2) 0.0325(4) Uani 1 1 d . . . . .
N9 N 0.12331(15) 0.3417(2) 0.3473(3) 0.0393(4) Uani 1 1 d . . . . .
N10 N 0.06824(14) 0.2822(2) 0.4627(3) 0.0405(5) Uani 1 1 d . . . . .
H7A H 0.6662(17) 1.010(3) 0.930(3) 0.044(6) Uiso 1 1 d . . . . .
H9A H 0.119(2) 0.436(3) 0.353(3) 0.068(8) Uiso 1 1 d . . . . .
H7B H 0.5679(17) 0.940(2) 0.841(3) 0.039(6) Uiso 1 1 d . . . . .
H7C H 0.5954(18) 0.944(2) 1.029(3) 0.055(7) Uiso 1 1 d . . . . .
H9B H 0.195(2) 0.322(3) 0.388(4) 0.074(9) Uiso 1 1 d . . . . .
H8A H 0.6835(19) 0.796(3) 0.841(4) 0.061(8) Uiso 1 1 d . . . . .
H8B H 0.6335(19) 0.746(3) 0.958(3) 0.053(7) Uiso 1 1 d . . . . .
H10A H 0.018(3) 0.243(4) 0.400(4) 0.093(11) Uiso 1 1 d . . . . .
H9C H 0.101(2) 0.314(3) 0.244(4) 0.085(11) Uiso 1 1 d . . . . .
H10B H 0.049(2) 0.352(3) 0.508(4) 0.089(12) Uiso 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
O1 N4 1.231(2) . ?
O2 N4 1.2291(19) . ?
O3 N6 1.2517(19) . ?
O4 N6 1.2598(18) . ?
O5 N5 1.2426(18) . ?
O6 N5 1.2513(19) . ?
N1 N2 1.322(2) . ?
N1 C1 1.341(2) . ?
N2 N3 1.351(2) . ?
N3 C2 1.342(2) . ?
N4 C1 1.419(2) . ?
N5 C3 1.388(2) . ?
N6 C3 1.374(2) . ?
C1 C2 1.384(2) . ?
C2 C3 1.459(2) . ?
N7 N8 1.444(2) . ?
N7 H7A 0.93(3) . ?
N7 H7B 0.94(2) . ?
N7 H7C 0.94(3) . ?
N8 H8A 0.87(3) . ?
N8 H8B 0.88(3) . ?
N9 N10 1.443(3) . ?
N9 H9A 0.92(3) . ?
N9 H9B 0.98(3) . ?
N9 H9C 0.88(3) . ?
N10 H10A 0.86(3) . ?
N10 H10B 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
N2 N1 C1 105.52(14) . . ?
N1 N2 N3 111.11(14) . . ?
C2 N3 N2 107.73(14) . . ?
O2 N4 O1 123.13(16) . . ?
O2 N4 C1 118.11(15) . . ?
O1 N4 C1 118.75(15) . . ?
O5 N5 O6 120.03(14) . . ?
O5 N5 C3 123.71(14) . . ?
O6 N5 C3 116.26(14) . . ?
O3 N6 O4 119.64(14) . . ?
O3 N6 C3 117.27(14) . . ?
O4 N6 C3 123.08(14) . . ?
N1 C1 C2 110.33(15) . . ?
N1 C1 N4 120.58(15) . . ?
C2 C1 N4 129.09(16) . . ?
N3 C2 C1 105.30(15) . . ?
N3 C2 C3 123.45(15) . . ?
C1 C2 C3 131.22(16) . . ?
N6 C3 N5 121.32(15) . . ?
N6 C3 C2 119.15(15) . . ?
N5 C3 C2 119.50(15) . . ?
N8 N7 H7A 108.8(14) . . ?
N8 N7 H7B 112.5(13) . . ?
H7A N7 H7B 111.5(19) . . ?
N8 N7 H7C 107.3(15) . . ?
H7A N7 H7C 110(2) . . ?
H7B N7 H7C 107.0(19) . . ?
N7 N8 H8A 103.0(18) . . ?
N7 N8 H8B 104.4(16) . . ?
H8A N8 H8B 103(2) . . ?
N10 N9 H9A 108.7(17) . . ?
N10 N9 H9B 108.5(17) . . ?
H9A N9 H9B 104(2) . . ?
N10 N9 H9C 113(2) . . ?
H9A N9 H9C 110(3) . . ?
H9B N9 H9C 112(3) . . ?
N9 N10 H10A 104(2) . . ?
N9 N10 H10B 103(2) . . ?
H10A N10 H10B 110(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 1.1(2) . . . . ?
N1 N2 N3 C2 -1.0(2) . . . . ?
N2 N1 C1 C2 -0.8(2) . . . . ?
N2 N1 C1 N4 178.44(16) . . . . ?
O2 N4 C1 N1 -166.71(17) . . . . ?
O1 N4 C1 N1 13.0(3) . . . . ?
O2 N4 C1 C2 12.4(3) . . . . ?
O1 N4 C1 C2 -167.87(18) . . . . ?
N2 N3 C2 C1 0.49(19) . . . . ?
N2 N3 C2 C3 178.78(16) . . . . ?
N1 C1 C2 N3 0.2(2) . . . . ?
N4 C1 C2 N3 -178.97(17) . . . . ?
N1 C1 C2 C3 -177.90(17) . . . . ?
N4 C1 C2 C3 2.9(3) . . . . ?
O3 N6 C3 N5 -179.56(15) . . . . ?
O4 N6 C3 N5 0.9(2) . . . . ?
O3 N6 C3 C2 -1.6(2) . . . . ?
O4 N6 C3 C2 178.82(15) . . . . ?
O5 N5 C3 N6 1.1(3) . . . . ?
O6 N5 C3 N6 -178.39(15) . . . . ?
O5 N5 C3 C2 -176.89(15) . . . . ?
O6 N5 C3 C2 3.7(2) . . . . ?
N3 C2 C3 N6 -120.28(19) . . . . ?
C1 C2 C3 N6 57.5(3) . . . . ?
N3 C2 C3 N5 57.7(2) . . . . ?
C1 C2 C3 N5 -124.5(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
N10 H10B O1 0.84(3) 2.39(3) 3.122(3) 147(3) 4_576
N9 H9C N10 0.88(3) 2.43(3) 3.302(3) 170(3) 4_565
N10 H10A N1 0.86(3) 2.37(3) 3.134(3) 148(3) 2_545
N8 H8B O5 0.88(3) 2.30(3) 3.109(2) 154(2) 4_576
N8 H8B O4 0.88(3) 2.62(3) 3.229(2) 126.8(19) 2_646
N8 H8A O5 0.87(3) 2.62(3) 3.113(2) 116(2) .
N8 H8A O2 0.87(3) 2.49(3) 3.099(2) 128(2) 3_676
N9 H9B N8 0.98(3) 1.99(3) 2.909(3) 156(2) 2_646
N7 H7C N6 0.94(3) 2.54(3) 3.310(2) 139.4(19) 3_677
N7 H7C O4 0.94(3) 1.99(3) 2.910(2) 168(2) 3_677
N7 H7B O5 0.94(2) 2.05(2) 2.823(2) 139.1(18) .
N7 H7B O4 0.94(2) 2.11(2) 2.921(2) 143.7(18) .
N9 H9A N2 0.92(3) 2.04(3) 2.926(3) 161(2) .
N7 H7A N3 0.93(3) 1.93(3) 2.840(2) 166(2) 2_656

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

