# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2084791'
loop_
_audit_author_name
_audit_author_address
'yu wang'
;Northwest University
China
;
_audit_update_record             
;
2021-05-20 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_audit_creation_date             2020-06-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H8 N10'
_chemical_formula_sum            'C4 H8 N10'
_chemical_formula_weight         196.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0488(14)
_cell_length_b                   13.078(2)
_cell_length_c                   6.7239(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.968(5)
_cell_angle_gamma                90
_cell_volume                     778.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5386
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      34.657
_cell_measurement_theta_min      2.779
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.5615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1407 before and 0.0816 after correction. The Ratio of minimum to maximum transmission is 0.7519. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   culumn
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10486
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.657
_diffrn_reflns_theta_min         2.301
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2677
_reflns_number_total             3276
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0678
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+0.6831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1707
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H9A(0.025) H10A(0.033) H10B(0.033) H00A(0.023) H00B(0.023)
 Fixed X: H9A(0.283977) H10A(1.095003) H10B(0.929626) H00A(0.7369)
 H00B(0.694489)
 Fixed Y: H9A(0.382438) H10A(0.511774) H10B(0.504841) H00A(0.372823)
 H00B(0.264718)
 Fixed Z: H9A(0.160828) H10A(0.769589) H10B(0.762067) H00A(0.816834)
 H00B(0.720352)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.51060(13) 0.36669(9) 0.43542(18) 0.0150(2) Uani 1 1 d . . . . .
N4 N 0.89990(13) 0.31108(9) 0.69721(19) 0.0166(2) Uani 1 1 d . . . . .
N9 N 0.33873(15) 0.43431(11) 0.1438(2) 0.0207(3) Uani 1 1 d . . . . .
H9A H 0.283977 0.382438 0.160828 0.025 Uiso 1 1 d GR . . . .
N5 N 0.94976(16) 0.21507(11) 0.6692(2) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.72017(15) 0.43867(11) 0.3937(2) 0.0232(3) Uani 1 1 d . . . . .
N10 N 1.01358(17) 0.47607(11) 0.7537(3) 0.0278(3) Uani 1 1 d . . . . .
H10A H 1.095003 0.511774 0.769589 0.033 Uiso 1 1 calc R . . . .
H10B H 0.929626 0.504841 0.762067 0.033 Uiso 1 1 calc R . . . .
N8 N 0.41565(15) 0.30459(12) 0.5225(2) 0.0247(3) Uani 1 1 d . . . . .
N2 N 0.60335(15) 0.46763(12) 0.2314(2) 0.0238(3) Uani 1 1 d . . . . .
N7 N 1.13914(15) 0.32224(12) 0.6992(2) 0.0254(3) Uani 1 1 d . . . . .
N6 N 1.09112(17) 0.22387(12) 0.6710(2) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.66192(15) 0.37869(11) 0.5108(2) 0.0156(2) Uani 1 1 d . . . . .
C1 C 0.47904(15) 0.42345(10) 0.2606(2) 0.0159(2) Uani 1 1 d . . . . .
C4 C 1.01750(16) 0.37588(12) 0.7159(2) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.74297(15) 0.32920(12) 0.7021(2) 0.0193(3) Uani 1 1 d . . . . .
H00A H 0.736900 0.372823 0.816834 0.023 Uiso 1 1 calc R . . . .
H00B H 0.694489 0.264718 0.720352 0.023 Uiso 1 1 calc R . . . .
H9B H 0.342(3) 0.4577(19) 0.023(4) 0.032(6) Uiso 1 1 d . . . . .
H8A H 0.344(3) 0.3451(19) 0.559(4) 0.035(6) Uiso 1 1 d . . . . .
H8B H 0.368(3) 0.259(2) 0.424(5) 0.046(8) 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
N3 N8 1.3960(17) . ?
N3 C2 1.3669(17) . ?
N3 C1 1.3695(18) . ?
N4 N5 1.3604(18) . ?
N4 C4 1.3458(19) . ?
N4 C3 1.4469(18) . ?
N9 H9A 0.8616 . ?
N9 C1 1.3548(19) . ?
N9 H9B 0.87(3) . ?
N5 N6 1.282(2) . ?
N1 N2 1.4047(19) . ?
N1 C2 1.2984(18) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N10 C4 1.337(2) . ?
N8 H8A 0.91(3) . ?
N8 H8B 0.93(3) . ?
N2 C1 1.3151(18) . ?
N7 N6 1.359(2) . ?
N7 C4 1.3295(19) . ?
C2 C3 1.490(2) . ?
C3 H00A 0.9700 . ?
C3 H00B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N3 N8 124.58(12) . . ?
C2 N3 C1 105.70(11) . . ?
C1 N3 N8 129.66(12) . . ?
N5 N4 C3 120.64(13) . . ?
C4 N4 N5 108.40(12) . . ?
C4 N4 C3 130.96(13) . . ?
H9A N9 H9B 122.2 . . ?
C1 N9 H9A 109.6 . . ?
C1 N9 H9B 111.3(17) . . ?
N6 N5 N4 105.95(13) . . ?
C2 N1 N2 107.42(12) . . ?
H10A N10 H10B 120.0 . . ?
C4 N10 H10A 120.0 . . ?
C4 N10 H10B 120.0 . . ?
N3 N8 H8A 108.1(16) . . ?
N3 N8 H8B 107.9(19) . . ?
H8A N8 H8B 109(2) . . ?
C1 N2 N1 107.14(12) . . ?
C4 N7 N6 105.37(13) . . ?
N5 N6 N7 112.08(13) . . ?
N3 C2 C3 123.10(12) . . ?
N1 C2 N3 110.23(12) . . ?
N1 C2 C3 126.66(13) . . ?
N9 C1 N3 123.92(13) . . ?
N2 C1 N3 109.50(12) . . ?
N2 C1 N9 126.52(13) . . ?
N10 C4 N4 125.69(14) . . ?
N7 C4 N4 108.20(14) . . ?
N7 C4 N10 126.05(14) . . ?
N4 C3 C2 111.17(11) . . ?
N4 C3 H00A 109.4 . . ?
N4 C3 H00B 109.4 . . ?
C2 C3 H00A 109.4 . . ?
C2 C3 H00B 109.4 . . ?
H00A C3 H00B 108.0 . . ?

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

data_0615wy_0m
_database_code_depnum_ccdc_archive 'CCDC 2084803'
loop_
_audit_author_name
_audit_author_address
'yu wang'
;Northwest University
China
;
_audit_update_record             
;
2021-05-20 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_audit_creation_date             2019-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H5 N5 O2'
_chemical_formula_sum            'C3 H5 N5 O2'
_chemical_formula_weight         143.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   9.7958(4)
_cell_length_b                   7.7989(3)
_cell_length_c                   14.7319(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1125.47(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3942
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.307
_cell_measurement_theta_min      2.765
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.0998
_exptl_absorpt_correction_T_min  0.0673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0851 before and 0.0600 after correction. The Ratio of minimum to maximum transmission is 0.6743. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_min         2.765
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1176
_reflns_number_total             1671
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.6520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.61017(12) 0.54823(14) 0.90980(7) 0.0240(3) Uani 1 1 d . . . . .
O1 O 0.62133(11) 0.78347(14) 0.82249(7) 0.0225(3) Uani 1 1 d . . . . .
N1 N 0.65324(13) 0.59135(17) 0.66925(8) 0.0204(3) Uani 1 1 d . . . . .
N3 N 0.77726(13) 0.73429(18) 0.57851(9) 0.0248(3) Uani 1 1 d . . . . .
N2 N 0.78326(13) 0.64544(18) 0.65195(9) 0.0242(3) Uani 1 1 d . . . . .
N4 N 0.64689(13) 0.74043(18) 0.54597(9) 0.0231(3) Uani 1 1 d . . . . .
N5 N 0.43529(14) 0.62300(19) 0.59777(10) 0.0250(3) Uani 1 1 d . . . . .
C3 C 0.61722(14) 0.6288(2) 0.83216(10) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.57076(16) 0.64998(19) 0.60313(10) 0.0204(3) Uani 1 1 d . . . . .
C2 C 0.62125(16) 0.5046(2) 0.75353(10) 0.0219(3) Uani 1 1 d . . . . .
H2A H 0.5324(18) 0.451(2) 0.7474(12) 0.029(5) Uiso 1 1 d . . . . .
H5A H 0.396(2) 0.665(3) 0.5477(15) 0.039(6) Uiso 1 1 d . . . . .
H2 H 0.611(2) 0.635(3) 0.9584(16) 0.055(7) Uiso 1 1 d . . . . .
H2B H 0.6878(19) 0.415(3) 0.7646(13) 0.032(5) Uiso 1 1 d . . . . .
H5B H 0.406(2) 0.524(3) 0.6170(13) 0.036(6) 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
O2 C3 1.3067(18) . ?
O1 C3 1.2154(19) . ?
N1 N2 1.3656(18) . ?
N1 C1 1.3456(19) . ?
N1 C2 1.4485(19) . ?
N3 N2 1.2861(19) . ?
N3 N4 1.3650(18) . ?
N4 C1 1.328(2) . ?
N5 C1 1.346(2) . ?
C3 C2 1.511(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C2 120.40(12) . . ?
C1 N1 N2 108.66(12) . . ?
C1 N1 C2 130.50(13) . . ?
N2 N3 N4 110.92(12) . . ?
N3 N2 N1 106.31(12) . . ?
C1 N4 N3 106.51(13) . . ?
O2 C3 C2 111.36(13) . . ?
O1 C3 O2 125.56(14) . . ?
O1 C3 C2 123.08(13) . . ?
N1 C1 N5 125.55(14) . . ?
N4 C1 N1 107.60(13) . . ?
N4 C1 N5 126.85(15) . . ?
N1 C2 C3 111.30(12) . . ?

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

data_20210312fl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2084804'
loop_
_audit_author_name
_audit_author_address
'yu wang'
;Northwest University
China
;
_audit_update_record             
;
2021-05-20 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H6 K2 N11 O6'
_chemical_formula_sum            'C4 H6 K2 N11 O6'
_chemical_formula_weight         382.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.3891 0.8535 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.0899(18)
_cell_length_b                   8.238(5)
_cell_length_c                   20.690(11)
_cell_angle_alpha                96.88(2)
_cell_angle_beta                 90.38(4)
_cell_angle_gamma                95.16(3)
_cell_volume                     689.2(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9310
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.86
_cell_measurement_theta_min      3.74
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    4.359
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5252
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1634 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.6995.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             386
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11667
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.167
_diffrn_reflns_theta_min         3.745
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2468
_reflns_number_total             2586
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.2804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0811
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00N(H00C,H00D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K2 K 0.86997(8) 0.85421(4) 0.58717(2) 0.01719(12) Uani 1 1 d . . . . .
K1 K 0.44655(10) -0.22109(5) 0.06526(2) 0.02613(13) Uani 1 1 d . . . . .
O003 O 0.5689(3) 0.90794(13) 0.37156(6) 0.0196(3) Uani 1 1 d . . . . .
O2 O 1.3172(3) 0.65123(15) 0.54327(7) 0.0207(3) Uani 1 1 d . . . . .
O005 O 0.8405(3) 0.84804(15) 0.45487(6) 0.0257(3) Uani 1 1 d . . . . .
O006 O 0.9073(4) -0.38820(17) 0.11847(7) 0.0306(3) Uani 1 1 d . . . . .
O6 O 0.0664(4) 0.31026(17) 0.02797(6) 0.0311(3) Uani 1 1 d . . . . .
N12 N -0.0393(3) 0.16878(16) 0.22916(6) 0.0150(3) Uani 1 1 d . . . . .
N11 N 0.0129(3) 0.58355(16) 0.25746(7) 0.0186(3) Uani 1 1 d . . . . .
N9 N 0.1580(3) 0.44979(16) 0.34063(6) 0.0150(3) Uani 1 1 d . . . . .
N10 N 0.2199(3) 0.68364(16) 0.29949(6) 0.0171(3) Uani 1 1 d . . . . .
N8 N 0.6402(3) 0.80525(16) 0.40842(6) 0.0165(3) Uani 1 1 d . . . . .
N7 N 0.5161(3) 0.65149(16) 0.40128(6) 0.0163(3) Uani 1 1 d . . . . .
O00E O 0.2813(4) 0.09051(18) 0.04795(6) 0.0390(4) Uani 1 1 d . . . . .
N15 N 0.2484(4) 0.00379(16) 0.16871(7) 0.0197(3) Uani 1 1 d . . . . .
N16 N 0.0069(4) 0.23809(17) 0.12506(7) 0.0219(3) Uani 1 1 d . . . . .
N14 N 0.2326(4) -0.03551(16) 0.23058(7) 0.0207(3) Uani 1 1 d . . . . .
N13 N 0.0620(4) 0.06213(16) 0.26729(7) 0.0187(3) Uani 1 1 d . . . . .
N17 N 0.1233(4) 0.20802(18) 0.06629(7) 0.0238(3) Uani 1 1 d . . . . .
C00K C 0.3059(4) 0.60263(18) 0.34863(7) 0.0136(3) Uani 1 1 d . . . . .
C00L C -0.0179(4) 0.44716(19) 0.28463(7) 0.0146(3) Uani 1 1 d . . . . .
C00M C 0.0778(4) 0.13427(19) 0.16878(8) 0.0165(3) Uani 1 1 d . . . . .
C00N C -0.2318(4) 0.3017(2) 0.25490(8) 0.0173(3) Uani 1 1 d . . . . .
H00C H -0.383218 0.262867 0.288108 0.021 Uiso 1 1 calc R . . . .
H00D H -0.365931 0.333593 0.219278 0.021 Uiso 1 1 calc R . . . .
H2A H 1.307(7) 0.565(4) 0.5580(14) 0.047(8) Uiso 1 1 d . . . . .
H2B H 1.321(6) 0.636(3) 0.5041(14) 0.042(7) Uiso 1 1 d . . . . .
H00A H 0.939(7) -0.389(3) 0.1598(15) 0.048(7) Uiso 1 1 d . . . . .
H00B H 0.926(9) -0.484(5) 0.1015(17) 0.072(10) 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
K2 K2 4.0899(18) 1_455 ?
K2 K2 4.0899(18) 1_655 ?
K2 K2 4.645(2) 2_776 ?
K2 O003 2.8358(17) 2_676 ?
K2 O003 2.9326(18) 2_776 ?
K2 O2 2.7678(18) 1_455 ?
K2 O2 2.6787(17) . ?
K2 O005 2.8596(19) 2_776 ?
K2 O005 2.7334(19) . ?
K2 N9 3.0597(19) 2_666 ?
K2 N8 3.289(2) 2_776 ?
K2 N13 3.013(2) 2_666 ?
K2 H2B 3.08(3) . ?
K1 K1 4.0899(18) 1_455 ?
K1 K1 4.0899(18) 1_655 ?
K1 K1 4.779(2) 2_655 ?
K1 O006 2.7965(19) 1_455 ?
K1 O006 2.7313(18) . ?
K1 O6 2.8640(19) 2_655 ?
K1 O6 2.827(2) 2 ?
K1 O00E 2.8819(19) 2_655 ?
K1 O00E 2.775(2) . ?
K1 N15 2.8307(19) . ?
K1 N17 3.258(2) 2_655 ?
O003 N8 1.2563(18) . ?
O2 H2A 0.80(3) . ?
O2 H2B 0.81(3) . ?
O005 N8 1.255(2) . ?
O006 H00A 0.86(3) . ?
O006 H00B 0.83(4) . ?
O6 N17 1.259(2) . ?
N12 N13 1.3390(19) . ?
N12 C00M 1.348(2) . ?
N12 C00N 1.457(2) . ?
N11 N10 1.359(2) . ?
N11 C00L 1.312(2) . ?
N9 C00K 1.338(2) . ?
N9 C00L 1.357(2) . ?
N10 C00K 1.343(2) . ?
N8 N7 1.312(2) . ?
N7 C00K 1.381(2) . ?
O00E N17 1.235(2) . ?
N15 N14 1.358(2) . ?
N15 C00M 1.333(2) . ?
N16 N17 1.313(2) . ?
N16 C00M 1.364(2) . ?
N14 N13 1.293(2) . ?
C00L C00N 1.486(2) . ?
C00N H00C 0.9900 . ?
C00N H00D 0.9900 . ?

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
K2 K2 K2 79.19(3) 1_655 2_776 ?
K2 K2 K2 100.81(3) 1_455 2_776 ?
K2 K2 K2 180.0 1_455 1_655 ?
K2 K2 H2B 49.0(5) 1_655 . ?
K2 K2 H2B 131.0(5) 1_455 . ?
K2 K2 H2B 76.2(5) 2_776 . ?
O003 K2 K2 134.19(3) 2_676 1_655 ?
O003 K2 K2 72.78(4) 2_776 2_776 ?
O003 K2 K2 87.96(4) 2_676 2_776 ?
O003 K2 K2 45.81(4) 2_676 1_455 ?
O003 K2 K2 43.90(3) 2_776 1_655 ?
O003 K2 K2 136.10(3) 2_776 1_455 ?
O003 K2 O003 90.29(5) 2_676 2_776 ?
O003 K2 O005 75.27(5) 2_676 2_776 ?
O003 K2 N9 116.61(5) 2_676 2_666 ?
O003 K2 N9 112.77(5) 2_776 2_666 ?
O003 K2 N8 79.13(5) 2_676 2_776 ?
O003 K2 N8 22.37(4) 2_776 2_776 ?
O003 K2 N13 71.29(5) 2_676 2_666 ?
O003 K2 N13 66.34(5) 2_776 2_666 ?
O003 K2 H2B 163.1(5) 2_676 . ?
O003 K2 H2B 90.6(5) 2_776 . ?
O2 K2 K2 137.84(4) . 1_455 ?
O2 K2 K2 87.42(5) . 2_776 ?
O2 K2 K2 103.51(5) 1_455 2_776 ?
O2 K2 K2 42.16(4) . 1_655 ?
O2 K2 K2 139.49(3) 1_455 1_655 ?
O2 K2 K2 40.51(3) 1_455 1_455 ?
O2 K2 O003 85.94(5) . 2_776 ?
O2 K2 O003 174.74(4) . 2_676 ?
O2 K2 O003 86.20(5) 1_455 2_676 ?
O2 K2 O003 175.01(4) 1_455 2_776 ?
O2 K2 O2 97.33(6) . 1_455 ?
O2 K2 O005 131.31(5) 1_455 2_776 ?
O2 K2 O005 75.61(5) . . ?
O2 K2 O005 99.47(6) . 2_776 ?
O2 K2 N9 72.04(5) 1_455 2_666 ?
O2 K2 N9 68.35(5) . 2_666 ?
O2 K2 N8 152.77(4) 1_455 2_776 ?
O2 K2 N8 96.09(5) . 2_776 ?
O2 K2 N13 110.35(5) . 2_666 ?
O2 K2 N13 115.65(5) 1_455 2_666 ?
O2 K2 H2B 14.0(5) . . ?
O2 K2 H2B 91.7(5) 1_455 . ?
O005 K2 K2 109.81(4) 2_776 1_455 ?
O005 K2 K2 70.19(4) 2_776 1_655 ?
O005 K2 K2 87.95(5) . 1_455 ?
O005 K2 K2 92.05(5) . 1_655 ?
O005 K2 K2 34.72(3) . 2_776 ?
O005 K2 K2 32.99(3) 2_776 2_776 ?
O005 K2 O003 104.39(5) . 2_776 ?
O005 K2 O003 44.07(4) 2_776 2_776 ?
O005 K2 O003 101.85(5) . 2_676 ?
O005 K2 O2 72.94(5) . 1_455 ?
O005 K2 O005 67.71(5) . 2_776 ?
O005 K2 N9 156.07(4) 2_776 2_666 ?
O005 K2 N9 124.92(4) . 2_666 ?
O005 K2 N8 87.69(5) . 2_776 ?
O005 K2 N8 22.18(4) 2_776 2_776 ?
O005 K2 N13 100.49(5) 2_776 2_666 ?
O005 K2 N13 167.85(4) . 2_666 ?
O005 K2 H2B 93.9(5) 2_776 . ?
O005 K2 H2B 61.7(5) . . ?
N9 K2 K2 154.09(3) 2_666 2_776 ?
N9 K2 K2 91.89(4) 2_666 1_455 ?
N9 K2 K2 88.11(4) 2_666 1_655 ?
N9 K2 N8 135.13(5) 2_666 2_776 ?
N9 K2 H2B 78.4(5) 2_666 . ?
N8 K2 K2 57.84(4) 2_776 1_655 ?
N8 K2 K2 122.16(4) 2_776 1_455 ?
N8 K2 K2 53.58(4) 2_776 2_776 ?
N8 K2 H2B 95.8(5) 2_776 . ?
N13 K2 K2 93.74(5) 2_666 1_455 ?
N13 K2 K2 86.26(5) 2_666 1_655 ?
N13 K2 K2 133.42(4) 2_666 2_776 ?
N13 K2 N9 67.09(5) 2_666 2_666 ?
N13 K2 N8 81.22(5) 2_666 2_776 ?
N13 K2 H2B 124.2(5) 2_666 . ?
K1 K1 K1 180.0 1_655 1_455 ?
K1 K1 K1 91.53(3) 1_455 2_655 ?
K1 K1 K1 88.47(3) 1_655 2_655 ?
O006 K1 K1 133.17(4) 1_455 2_655 ?
O006 K1 K1 131.34(4) . 2_655 ?
O006 K1 K1 41.67(4) 1_455 1_455 ?
O006 K1 K1 138.33(4) 1_455 1_655 ?
O006 K1 K1 137.10(4) . 1_455 ?
O006 K1 K1 42.90(4) . 1_655 ?
O006 K1 O006 95.43(6) . 1_455 ?
O006 K1 O6 135.05(5) 1_455 2_655 ?
O006 K1 O6 134.20(5) . 2 ?
O006 K1 O6 69.02(5) . 2_655 ?
O006 K1 O6 68.67(5) 1_455 2 ?
O006 K1 O00E 146.67(5) 1_455 2_655 ?
O006 K1 O00E 143.69(5) . . ?
O006 K1 O00E 108.62(6) . 2_655 ?
O006 K1 N15 105.36(6) . . ?
O006 K1 N15 75.32(6) 1_455 . ?
O006 K1 N17 90.46(5) . 2_655 ?
O006 K1 N17 143.26(5) 1_455 2_655 ?
O6 K1 K1 135.58(4) 2 1_655 ?
O6 K1 K1 75.51(4) 2_655 2_655 ?
O6 K1 K1 77.58(4) 2 2_655 ?
O6 K1 K1 43.70(4) 2_655 1_655 ?
O6 K1 K1 136.30(4) 2_655 1_455 ?
O6 K1 K1 44.42(4) 2 1_455 ?
O6 K1 O6 91.88(5) 2 2_655 ?
O6 K1 O00E 78.00(6) 2 2_655 ?
O6 K1 O00E 44.24(5) 2_655 2_655 ?
O6 K1 N15 110.92(5) 2 . ?
O6 K1 N17 81.34(6) 2 2_655 ?
O6 K1 N17 22.57(4) 2_655 2_655 ?
O00E K1 K1 70.98(5) . 1_455 ?
O00E K1 K1 109.02(5) . 1_655 ?
O00E K1 K1 31.68(3) 2_655 2_655 ?
O00E K1 K1 110.98(5) 2_655 1_455 ?
O00E K1 K1 69.02(5) 2_655 1_655 ?
O00E K1 K1 33.05(3) . 2_655 ?
O00E K1 O006 108.08(5) . 1_455 ?
O00E K1 O6 81.12(5) . 2 ?
O00E K1 O6 108.24(5) . 2_655 ?
O00E K1 O00E 64.73(5) . 2_655 ?
O00E K1 N15 57.12(5) . . ?
O00E K1 N17 22.14(4) 2_655 2_655 ?
O00E K1 N17 86.86(5) . 2_655 ?
N15 K1 K1 110.49(5) . 1_655 ?
N15 K1 K1 88.09(5) . 2_655 ?
N15 K1 K1 69.51(5) . 1_455 ?
N15 K1 O6 148.48(5) . 2_655 ?
N15 K1 O00E 117.87(5) . 2_655 ?
N15 K1 N17 137.51(5) . 2_655 ?
N17 K1 K1 53.81(4) 2_655 2_655 ?
N17 K1 K1 57.15(4) 2_655 1_655 ?
N17 K1 K1 122.85(4) 2_655 1_455 ?
K2 O003 K2 90.29(5) 2_676 2_776 ?
N8 O003 K2 120.39(9) . 2_676 ?
N8 O003 K2 94.98(9) . 2_776 ?
K2 O2 K2 97.33(5) . 1_655 ?
K2 O2 H2A 112(2) 1_655 . ?
K2 O2 H2A 115(2) . . ?
K2 O2 H2B 112.6(19) . . ?
K2 O2 H2B 108.1(19) 1_655 . ?
H2A O2 H2B 110(3) . . ?
K2 O005 K2 112.29(5) . 2_776 ?
N8 O005 K2 139.34(10) . . ?
N8 O005 K2 98.52(9) . 2_776 ?
K1 O006 K1 95.43(6) . 1_655 ?
K1 O006 H00A 110.0(18) 1_655 . ?
K1 O006 H00A 124.5(18) . . ?
K1 O006 H00B 101(2) 1_655 . ?
K1 O006 H00B 117(2) . . ?
H00A O006 H00B 106(3) . . ?
K1 O6 K1 91.88(5) 2 2_655 ?
N17 O6 K1 96.58(10) . 2_655 ?
N17 O6 K1 117.68(12) . 2 ?
N13 N12 C00M 109.16(13) . . ?
N13 N12 C00N 121.38(13) . . ?
C00M N12 C00N 129.40(14) . . ?
C00L N11 N10 102.65(14) . . ?
C00K N9 K2 137.27(11) . 2_666 ?
C00K N9 C00L 102.44(13) . . ?
C00L N9 K2 120.29(10) . 2_666 ?
C00K N10 N11 109.80(13) . . ?
O003 N8 K2 62.66(8) . 2_776 ?
O003 N8 N7 123.46(14) . . ?
O005 N8 K2 59.30(8) . 2_776 ?
O005 N8 O003 119.89(13) . . ?
O005 N8 N7 116.65(13) . . ?
N7 N8 K2 164.61(10) . 2_776 ?
N8 N7 C00K 116.68(13) . . ?
K1 O00E K1 115.27(5) . 2_655 ?
N17 O00E K1 96.31(11) . 2_655 ?
N17 O00E K1 148.35(12) . . ?
N14 N15 K1 121.11(10) . . ?
C00M N15 K1 131.26(11) . . ?
C00M N15 N14 105.18(13) . . ?
N17 N16 C00M 116.73(14) . . ?
N13 N14 N15 111.84(13) . . ?
N12 N13 K2 121.76(10) . 2_666 ?
N14 N13 K2 126.72(11) . 2_666 ?
N14 N13 N12 105.97(13) . . ?
O6 N17 K1 60.84(9) . 2_655 ?
O6 N17 N16 115.19(14) . . ?
O00E N17 K1 61.55(9) . 2_655 ?
O00E N17 O6 120.31(15) . . ?
O00E N17 N16 124.50(14) . . ?
N16 N17 K1 164.07(12) . 2_655 ?
N9 C00K N10 109.76(14) . . ?
N9 C00K N7 119.50(14) . . ?
N10 C00K N7 130.73(14) . . ?
N11 C00L N9 115.35(15) . . ?
N11 C00L C00N 121.19(15) . . ?
N9 C00L C00N 123.46(14) . . ?
N12 C00M N16 115.84(14) . . ?
N15 C00M N12 107.84(14) . . ?
N15 C00M N16 136.28(15) . . ?
N12 C00N C00L 111.47(13) . . ?
N12 C00N H00C 109.3 . . ?
N12 C00N H00D 109.3 . . ?
C00L C00N H00C 109.3 . . ?
C00L C00N H00D 109.3 . . ?
H00C C00N H00D 108.0 . . ?

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

data_20210511fl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2084806'
loop_
_audit_author_name
_audit_author_address
'yu wang'
;Northwest University
China
;
_audit_update_record             
;
2021-05-20 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_audit_creation_date             2021-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(N O3), C4 H10 N10'
_chemical_formula_sum            'C4 H10 N12 O6'
_chemical_formula_weight         322.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8163(2)
_cell_length_b                   18.5777(6)
_cell_length_c                   9.9513(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.2550(10)
_cell_angle_gamma                90
_cell_volume                     1243.74(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8178
_cell_measurement_temperature    173
_cell_measurement_theta_max      109.734
_cell_measurement_theta_min      8.275
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13953
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.877
_diffrn_reflns_theta_min         4.141
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2123
_reflns_number_total             2360
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.4514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0804
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N9(H9A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N7(H7)
2.d X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N10(H10A,H10B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 1.05214(13) 0.33392(5) -0.08009(9) 0.0220(2) Uani 1 1 d . . . . .
O4 O 0.43083(13) 0.47422(5) 0.77178(9) 0.0216(2) Uani 1 1 d . . . . .
O6 O 0.20803(16) 0.55723(5) 0.71296(10) 0.0278(2) Uani 1 1 d . . . . .
O1 O 1.07508(15) 0.37468(6) -0.28057(10) 0.0282(2) Uani 1 1 d . . . . .
O3 O 0.80985(14) 0.39593(5) -0.19282(10) 0.0253(2) Uani 1 1 d . . . . .
O5 O 0.22346(15) 0.50410(6) 0.90733(10) 0.0267(2) Uani 1 1 d . . . . .
N4 N 0.55040(15) 0.29334(5) 0.19003(10) 0.0155(2) Uani 1 1 d . . . . .
N8 N 0.26858(15) 0.40838(6) 0.30726(10) 0.0150(2) Uani 1 1 d . . . . .
N1 N 0.79340(15) 0.31533(6) 0.08807(11) 0.0182(2) Uani 1 1 d . . . . .
H1 H 0.865820 0.329442 0.027280 0.022 Uiso 1 1 calc R . . . .
N11 N 0.28677(16) 0.51174(6) 0.79859(11) 0.0181(2) Uani 1 1 d . . . . .
N9 N 0.20787(17) 0.43262(6) 0.17381(11) 0.0187(2) Uani 1 1 d . . . . .
H9A H 0.082204 0.445819 0.163365 0.022 Uiso 1 1 d GR . . . .
N7 N 0.33607(17) 0.39711(6) 0.52287(11) 0.0209(3) Uani 1 1 d . . . . .
H7 H 0.352104 0.406879 0.610482 0.025 Uiso 1 1 calc R . . . .
N12 N 0.97932(16) 0.36869(6) -0.18611(11) 0.0182(2) Uani 1 1 d . . . . .
N5 N 0.47944(16) 0.35730(6) -0.02078(11) 0.0206(2) Uani 1 1 d . . . . .
H5A H 0.528582 0.376002 -0.089507 0.025 Uiso 1 1 calc R . . . .
H5B H 0.351330 0.360542 -0.018108 0.025 Uiso 1 1 calc R . . . .
N10 N 0.22802(17) 0.51286(6) 0.44002(12) 0.0214(3) Uani 1 1 d . . . . .
H10A H 0.237068 0.531751 0.521873 0.026 Uiso 1 1 calc R . . . .
H10B H 0.188244 0.539486 0.367625 0.026 Uiso 1 1 calc R . . . .
N6 N 0.37271(17) 0.33032(6) 0.47058(11) 0.0214(3) Uani 1 1 d . . . . .
N3 N 0.71975(16) 0.26747(6) 0.26862(11) 0.0219(3) Uani 1 1 d . . . . .
N2 N 0.86460(17) 0.28095(6) 0.20628(12) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.59716(18) 0.32457(7) 0.07768(12) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.33085(18) 0.33922(7) 0.33994(13) 0.0161(3) Uani 1 1 d . . . . .
C4 C 0.27393(18) 0.44485(7) 0.42588(13) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.35754(18) 0.28432(7) 0.23527(13) 0.0168(3) Uani 1 1 d . . . . .
H2A H 0.349260 0.235528 0.273952 0.020 Uiso 1 1 calc R . . . .
H2B H 0.249684 0.289171 0.156322 0.020 Uiso 1 1 calc R . . . .
H9B H 0.282(3) 0.4712(10) 0.1586(18) 0.028(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
O2 N12 1.2682(14) . ?
O4 N11 1.2671(14) . ?
O6 N11 1.2575(15) . ?
O1 N12 1.2327(15) . ?
O3 N12 1.2530(14) . ?
O5 N11 1.2359(15) . ?
N4 N3 1.3728(15) . ?
N4 C1 1.3428(16) . ?
N4 C2 1.4660(16) . ?
N8 N9 1.4003(15) . ?
N8 C3 1.3757(16) . ?
N8 C4 1.3564(16) . ?
N1 N2 1.3578(16) . ?
N1 C1 1.3360(16) . ?
N7 N6 1.3836(16) . ?
N7 C4 1.3289(17) . ?
N5 C1 1.3117(17) . ?
N10 C4 1.3146(17) . ?
N6 C3 1.2960(17) . ?
N3 N2 1.2726(17) . ?
C3 C2 1.4896(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
N3 N4 C2 119.89(10) . . ?
C1 N4 N3 109.59(10) . . ?
C1 N4 C2 130.52(10) . . ?
C3 N8 N9 123.88(10) . . ?
C4 N8 N9 128.84(11) . . ?
C4 N8 C3 107.26(10) . . ?
C1 N1 N2 109.96(11) . . ?
O6 N11 O4 119.19(11) . . ?
O5 N11 O4 120.85(11) . . ?
O5 N11 O6 119.95(11) . . ?
C4 N7 N6 112.40(10) . . ?
O1 N12 O2 119.73(11) . . ?
O1 N12 O3 121.31(11) . . ?
O3 N12 O2 118.96(11) . . ?
C3 N6 N7 103.82(10) . . ?
N2 N3 N4 107.49(10) . . ?
N3 N2 N1 108.53(10) . . ?
N1 C1 N4 104.40(11) . . ?
N5 C1 N4 128.58(12) . . ?
N5 C1 N1 127.01(12) . . ?
N8 C3 C2 122.81(11) . . ?
N6 C3 N8 111.47(11) . . ?
N6 C3 C2 125.60(11) . . ?
N7 C4 N8 105.04(11) . . ?
N10 C4 N8 126.84(12) . . ?
N10 C4 N7 128.11(12) . . ?
N4 C2 C3 110.66(10) . . ?

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

data_a_a
_database_code_depnum_ccdc_archive 'CCDC 2084805'
loop_
_audit_author_name
_audit_author_address
'yu wang'
;Northwest University
China
;
_audit_update_record             
;
2021-05-20 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 N11 O4, H4 N O, 2(H2 O)'
_chemical_formula_sum            'C4 H11 N12 O7'
_chemical_formula_weight         339.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.8946(11)
_cell_length_b                   14.070(4)
_cell_length_c                   23.813(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.162(9)
_cell_angle_gamma                90
_cell_volume                     1303.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3100
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      22.41
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.4168
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1680 before and 0.1069 after correction.
The Ratio of minimum to maximum transmission is 0.5596.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             700
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1808
_diffrn_reflns_av_unetI/netI     0.1088
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16456
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.600
_diffrn_reflns_theta_min         2.896
_diffrn_ambient_temperature      179.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1424
_reflns_number_total             2418
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1721
_refine_ls_R_factor_gt           0.1056
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0888P)²+6.8840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2375
_refine_ls_wR_factor_ref         0.2709
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O7(H7A,H7B), O6(H6A,H6B)
2.b Rotating group:
 N12(H12A,H12B)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5822(12) 0.3517(4) 0.33190(19) 0.0339(12) Uani 1 1 d . . . . .
O8 O -0.2693(11) 0.5806(4) 0.46656(19) 0.0354(12) Uani 1 1 d . . . . .
H8 H -0.207992 0.581333 0.433119 0.053 Uiso 1 1 calc GR . . . .
O2 O -0.0557(12) 0.8213(4) 0.5064(2) 0.0379(13) Uani 1 1 d . . . . .
O4 O 0.5436(12) 0.3040(4) 0.4184(2) 0.0366(12) Uani 1 1 d . . . . .
O7 O 0.9713(13) 1.1713(4) 0.3363(2) 0.0403(13) Uani 1 1 d . . . . .
H7A H 0.900742 1.226682 0.324399 0.060 Uiso 1 1 d G . . . .
H7B H 0.939681 1.129514 0.309615 0.060 Uiso 1 1 d G . . . .
N4 N -0.0193(12) 0.7975(4) 0.3191(2) 0.0268(13) Uani 1 1 d . . . . .
N8 N 0.1240(13) 0.5849(4) 0.2752(2) 0.0273(13) Uani 1 1 d . . . . .
O1 O 0.1914(14) 0.9350(4) 0.4619(2) 0.0471(15) Uani 1 1 d . . . . .
N1 N 0.2703(13) 0.9168(4) 0.3506(2) 0.0289(13) Uani 1 1 d . . . . .
H1 H 0.366753 0.960189 0.372634 0.035 Uiso 1 1 calc R . . . .
N9 N 0.2706(13) 0.5032(4) 0.2978(2) 0.0291(13) Uani 1 1 d . . . . .
N3 N 0.1182(13) 0.8394(4) 0.2742(2) 0.0304(14) Uani 1 1 d . . . . .
N5 N -0.0329(13) 0.8087(4) 0.4157(2) 0.0306(14) Uani 1 1 d . . . . .
N7 N -0.0003(13) 0.5741(4) 0.3659(2) 0.0290(14) Uani 1 1 d . . . . .
N2 N 0.2900(13) 0.9107(4) 0.2936(2) 0.0292(14) Uani 1 1 d . . . . .
N10 N 0.2702(13) 0.4332(4) 0.3937(2) 0.0276(13) Uani 1 1 d . . . . .
N11 N 0.4699(13) 0.3608(4) 0.3801(2) 0.0286(13) Uani 1 1 d . . . . .
N6 N 0.0408(14) 0.8573(5) 0.4609(2) 0.0332(14) Uani 1 1 d . . . . .
N12 N -0.0124(14) 0.6244(4) 0.5016(2) 0.0306(14) Uani 1 1 d . . . . .
H12A H 0.190477 0.603009 0.492420 0.037 Uiso 1 1 d GR . . . .
H12B H -0.018673 0.686536 0.497674 0.037 Uiso 1 1 d GR . . . .
O6 O 0.5341(15) 1.0848(5) 0.4134(3) 0.0614(17) Uani 1 1 d . . . . .
H6A H 0.670974 1.111600 0.390202 0.092 Uiso 1 1 d G . . . .
H6B H 0.661602 1.075017 0.443691 0.092 Uiso 1 1 d G . . . .
C4 C 0.1915(14) 0.4983(5) 0.3533(3) 0.0247(15) Uani 1 1 d . . . . .
C3 C -0.0342(15) 0.6218(5) 0.3174(3) 0.0261(15) Uani 1 1 d . . . . .
C1 C 0.0771(15) 0.8445(5) 0.3662(3) 0.0249(15) Uani 1 1 d . . . . .
C2 C -0.2311(15) 0.7128(5) 0.3114(3) 0.0274(15) Uani 1 1 d . . . . .
H2A H -0.345203 0.714821 0.273608 0.033 Uiso 1 1 calc R . . . .
H2B H -0.412916 0.713558 0.339400 0.033 Uiso 1 1 calc R . . . .
H12C H -0.02(3) 0.604(8) 0.545(4) 0.10(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
O3 N11 1.250(7) . ?
O8 H8 0.8400 . ?
O8 N12 1.419(7) . ?
O2 N6 1.266(7) . ?
O4 N11 1.240(7) . ?
O7 H7A 0.8701 . ?
O7 H7B 0.8705 . ?
N4 N3 1.350(7) . ?
N4 C1 1.342(8) . ?
N4 C2 1.457(8) . ?
N8 N9 1.384(8) . ?
N8 C3 1.306(8) . ?
O1 N6 1.241(8) . ?
N1 H1 0.8800 . ?
N1 N2 1.365(8) . ?
N1 C1 1.327(8) . ?
N9 C4 1.369(8) . ?
N3 N2 1.283(8) . ?
N5 N6 1.297(8) . ?
N5 C1 1.368(8) . ?
N7 C4 1.343(8) . ?
N7 C3 1.337(8) . ?
N10 N11 1.329(7) . ?
N10 C4 1.355(8) . ?
N12 H12A 0.8806 . ?
N12 H12B 0.8798 . ?
N12 H12C 1.08(10) . ?
O6 H6A 0.8689 . ?
O6 H6B 0.8701 . ?
C3 C2 1.496(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

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
N12 O8 H8 109.5 . . ?
H7A O7 H7B 109.5 . . ?
N3 N4 C2 119.8(5) . . ?
C1 N4 N3 109.9(5) . . ?
C1 N4 C2 130.3(5) . . ?
C3 N8 N9 103.3(5) . . ?
N2 N1 H1 126.8 . . ?
C1 N1 H1 126.8 . . ?
C1 N1 N2 106.4(5) . . ?
C4 N9 N8 108.2(5) . . ?
N2 N3 N4 105.8(5) . . ?
N6 N5 C1 117.0(6) . . ?
C3 N7 C4 104.1(5) . . ?
N3 N2 N1 111.1(5) . . ?
N11 N10 C4 117.6(6) . . ?
O3 N11 N10 122.1(6) . . ?
O4 N11 O3 122.0(6) . . ?
O4 N11 N10 115.8(5) . . ?
O2 N6 N5 115.8(6) . . ?
O1 N6 O2 119.5(6) . . ?
O1 N6 N5 124.7(6) . . ?
O8 N12 H12A 109.0 . . ?
O8 N12 H12B 110.6 . . ?
O8 N12 H12C 115(6) . . ?
H12A N12 H12B 109.5 . . ?
H12A N12 H12C 101.5 . . ?
H12B N12 H12C 111.1 . . ?
H6A O6 H6B 104.6 . . ?
N7 C4 N9 108.8(6) . . ?
N7 C4 N10 119.4(6) . . ?
N10 C4 N9 131.8(6) . . ?
N8 C3 N7 115.5(6) . . ?
N8 C3 C2 121.4(6) . . ?
N7 C3 C2 123.0(6) . . ?
N4 C1 N5 116.9(6) . . ?
N1 C1 N4 106.8(6) . . ?
N1 C1 N5 136.4(6) . . ?
N4 C2 C3 113.7(5) . . ?
N4 C2 H2A 108.8 . . ?
N4 C2 H2B 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT430_a_a                 
;
PROBLEM: Short Inter D...A Contact  O3       ..N3       .       2.83 Ang.  
                                           1-x,-1/2+y,1/2-z  =      2_645 Check   
RESPONSE: High-density energetic materials often display close contacts.
;
# end Validation Reply Form
