# 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_WPF240415_1_a
_database_code_depnum_ccdc_archive 'CCDC 2322435'
loop_
_audit_author_name
_audit_author_address
'Pengfei Wang'
;University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'N5, C H5 N2'
_chemical_formula_sum            'C H5 N7'
_chemical_formula_weight         115.12

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

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

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

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

_cell_length_a                   4.9752(6)
_cell_length_b                   15.7038(18)
_cell_length_c                   7.0385(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.756(4)
_cell_angle_gamma                90
_cell_volume                     523.72(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1361
_cell_measurement_theta_min      4.00
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6511
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            2234
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.594
_diffrn_reflns_theta_max         27.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             596
_reflns_number_gt                487
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0426P)²+0.0880P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         596
_refine_ls_number_parameters     38
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
N4 N 0.27160(18) 0.38410(5) 0.64848(14) 0.0399(3) Uani 1 1 d . . . . .
H4A H 0.264457 0.438812 0.645305 0.048 Uiso 1 1 calc R U . . .
H4B H 0.126481 0.354767 0.583973 0.048 Uiso 1 1 calc R U . . .
C1 C 0.500000 0.34601(9) 0.750000 0.0371(4) Uani 1 2 d S T P . .
H1 H 0.499999 0.286791 0.749998 0.045 Uiso 1 2 calc R U P . .
N1 N 0.500000 0.70110(8) 0.750000 0.0434(4) Uani 1 2 d S T P . .
N2 N 0.28982(19) 0.65207(5) 0.65257(14) 0.0412(3) Uani 1 1 d . . . . .
N3 N 0.3696(2) 0.57301(5) 0.68964(15) 0.0450(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4 C1 1.2901(11) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C1 H1 0.9300 . ?
N1 N2 1.3111(11) 2_656 ?
N1 N2 1.3111(12) . ?
N2 N3 1.3054(12) . ?
N3 N3 1.3161(19) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N4 C1 N4 124.76(14) 2_656 . ?
N4 C1 H1 117.6 2_656 . ?
N4 C1 H1 117.6 . . ?
N2 N1 N2 108.08(12) 2_656 . ?
N3 N2 N1 107.97(9) . . ?
N2 N3 N3 107.99(6) . 2_656 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 N2 N3 0.02(5) 2_656 . . . ?
N1 N2 N3 N3 -0.05(14) . . . 2_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4A N3 0.86 2.17 3.0061(12) 163.7 . yes
N4 H4B N2 0.86 2.23 3.0007(13) 149.2 5_566 yes

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2322440'
loop_
_audit_author_name
_audit_author_address
'Pengfei Wang'
;University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2021-04-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H8 N3 O, N5'
_chemical_formula_sum            'C3 H8 N8 O'
_chemical_formula_weight         172.17
_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                   4.8465(4)
_cell_length_b                   9.6906(7)
_cell_length_c                   16.5974(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.765(2)
_cell_angle_gamma                90
_cell_volume                     778.60(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4827
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7452
_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 0.1311 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.7048.
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    1.469
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6507
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         2.434
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1097
_reflns_number_total             1376
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.040
_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)+(0.0468P)²+0.2969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b X=CH2 refined with riding coordinates:
 N8(H8A,H8B), N7(H7A,H7B), N6(H6A,H6B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.2189(3) 0.16191(13) 0.29149(7) 0.0272(4) Uani 1 1 d . . . . .
N4 N 1.1026(3) -0.21293(17) 0.38615(9) 0.0286(4) Uani 1 1 d . . . . .
N1 N 0.8786(3) -0.22072(17) 0.49329(9) 0.0301(4) Uani 1 1 d . . . . .
N3 N 1.1924(3) -0.31868(16) 0.42851(9) 0.0269(4) Uani 1 1 d . . . . .
N8 N 0.3952(3) -0.02107(16) 0.11941(8) 0.0236(4) Uani 1 1 d . . . . .
H8A H 0.284852 -0.055790 0.082673 0.028 Uiso 1 1 calc R U . . .
H8B H 0.518276 0.037906 0.106619 0.028 Uiso 1 1 calc R U . . .
N2 N 1.0531(3) -0.32417(15) 0.49539(9) 0.0256(4) Uani 1 1 d . . . . .
N7 N 0.1917(3) -0.14710(14) 0.21611(9) 0.0203(4) Uani 1 1 d . . . . .
H7A H 0.078794 -0.183384 0.180582 0.024 Uiso 1 1 calc R U . . .
H7B H 0.183456 -0.169553 0.266065 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3761(3) -0.05768(16) 0.19415(10) 0.0159(4) Uani 1 1 d . . . . .
N6 N 0.5173(3) 0.09289(15) 0.39156(8) 0.0223(4) Uani 1 1 d . . . . .
H6A H 0.443688 0.144812 0.426642 0.027 Uiso 1 1 calc R U . . .
H6B H 0.656391 0.041675 0.405563 0.027 Uiso 1 1 calc R U . . .
N5 N 0.9074(3) -0.15179(16) 0.42635(9) 0.0292(4) Uani 1 1 d . . . . .
C2 C 0.5694(3) 0.00093(17) 0.25830(10) 0.0171(4) Uani 1 1 d . . . . .
H2A H 0.710658 0.054897 0.233378 0.021 Uiso 1 1 calc R U . . .
H2B H 0.659852 -0.073813 0.288118 0.021 Uiso 1 1 calc R U . . .
C1 C 0.4168(3) 0.09182(17) 0.31617(10) 0.0167(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 C1 1.229(2) . ?
N4 N3 1.306(2) . ?
N4 N5 1.324(2) . ?
N1 N2 1.311(2) . ?
N1 N5 1.309(2) . ?
N3 N2 1.328(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N8 C3 1.298(2) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C3 1.309(2) . ?
C3 C2 1.496(2) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C1 1.321(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.521(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
N3 N4 N5 107.92(15) . . ?
N5 N1 N2 108.52(15) . . ?
N4 N3 N2 108.18(14) . . ?
H8A N8 H8B 120.0 . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
N1 N2 N3 107.48(14) . . ?
H7A N7 H7B 120.0 . . ?
C3 N7 H7A 120.0 . . ?
C3 N7 H7B 120.0 . . ?
N8 C3 N7 121.89(16) . . ?
N8 C3 C2 120.36(15) . . ?
N7 C3 C2 117.75(15) . . ?
H6A N6 H6B 120.0 . . ?
C1 N6 H6A 120.0 . . ?
C1 N6 H6B 120.0 . . ?
N1 N5 N4 107.90(14) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C3 C2 C1 111.26(13) . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
O1 C1 N6 123.89(16) . . ?
O1 C1 C2 120.31(15) . . ?
N6 C1 C2 115.75(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 N3 N2 N1 -0.14(19) . . . . ?
N3 N4 N5 N1 -0.1(2) . . . . ?
N8 C3 C2 C1 113.56(17) . . . . ?
N2 N1 N5 N4 0.0(2) . . . . ?
N7 C3 C2 C1 -67.14(19) . . . . ?
C3 C2 C1 O1 -34.6(2) . . . . ?
C3 C2 C1 N6 147.71(15) . . . . ?
N5 N4 N3 N2 0.12(19) . . . . ?
N5 N1 N2 N3 0.1(2) . . . . ?

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2322439'
loop_
_audit_author_name
_audit_author_address
'Pengfei Wang'
;University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2021-12-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H2 O, C3 H6 N5, N5'
_chemical_formula_sum            'C3 H8 N10 O'
_chemical_formula_weight         200.19
_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                   6.450(5)
_cell_length_b                   12.008(10)
_cell_length_c                   12.141(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.19(3)
_cell_angle_gamma                90
_cell_volume                     919.0(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1117
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      22.40
_cell_measurement_theta_min      3.39
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_av_unetI/netI     0.1197
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3729
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.302
_diffrn_reflns_theta_max         24.302
_diffrn_reflns_theta_min         2.413
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                785
_reflns_number_total             1478
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1478
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.034
_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)+(0.0464P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.c X=CH2 refined with riding coordinates:
 N6(H6A,H6B), N7(H7A,H7B)
;
_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
O1 O 0.2798(5) 0.45207(19) 0.67350(19) 0.0541(8) Uani 1 1 d G . . . .
H1A H 0.269651 0.484275 0.734505 0.081 Uiso 1 1 d G U . . .
H1B H 0.287289 0.383147 0.689880 0.081 Uiso 1 1 d G U . . .
N6 N 0.2332(4) 0.5722(2) 0.4749(2) 0.0426(9) Uani 1 1 d . . . . .
H6A H 0.227614 0.640771 0.494357 0.051 Uiso 1 1 calc R U . . .
H6B H 0.237621 0.520278 0.524191 0.051 Uiso 1 1 calc R U . . .
N7 N 0.2289(4) 0.6189(2) 0.2906(2) 0.0416(8) Uani 1 1 d . . . . .
H7A H 0.223134 0.688920 0.304359 0.050 Uiso 1 1 calc R U . . .
H7B H 0.230533 0.596446 0.223497 0.050 Uiso 1 1 calc R U . . .
N8 N 0.2442(4) 0.4333(2) 0.3451(2) 0.0330(8) Uani 1 1 d . . . . .
N9 N 0.2177(5) 0.3555(2) 0.4238(3) 0.0501(9) Uani 1 1 d . . . . .
N10 N 0.2866(5) 0.2746(2) 0.2678(2) 0.0526(10) Uani 1 1 d . . . . .
C1 C 0.2350(5) 0.5469(3) 0.3711(3) 0.0310(9) Uani 1 1 d . . . . .
C2 C 0.2843(6) 0.3818(3) 0.2537(3) 0.0464(10) Uani 1 1 d . . . . .
H2 H 0.307205 0.417740 0.189419 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2445(6) 0.2631(3) 0.3721(3) 0.0522(12) Uani 1 1 d . . . . .
H3 H 0.235275 0.193639 0.404638 0.063 Uiso 1 1 calc R U . . .
N1 N 0.2346(5) 0.6574(3) 0.8923(3) 0.0557(10) Uani 1 1 d . . . . .
N2 N 0.2391(5) 0.6818(2) 0.9987(3) 0.0514(10) Uani 1 1 d . . . . .
N3 N 0.2457(5) 0.5879(2) 1.0544(2) 0.0470(9) Uani 1 1 d . . . . .
N4 N 0.2463(5) 0.5062(2) 0.9837(3) 0.0505(9) Uani 1 1 d . . . . .
N5 N 0.2394(5) 0.5490(3) 0.8835(3) 0.0525(9) 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 H1A 0.8501 . ?
O1 H1B 0.8501 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C1 1.298(4) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C1 1.300(4) . ?
N8 N9 1.373(3) . ?
N8 C1 1.403(4) . ?
N8 C2 1.344(4) . ?
N9 C3 1.304(4) . ?
N10 C2 1.298(4) . ?
N10 C3 1.357(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
N1 N2 1.319(4) . ?
N1 N5 1.308(4) . ?
N2 N3 1.311(3) . ?
N3 N4 1.304(4) . ?
N4 N5 1.312(4) . ?

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
H1A O1 H1B 104.5 . . ?
H6A N6 H6B 120.0 . . ?
C1 N6 H6A 120.0 . . ?
C1 N6 H6B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C1 N7 H7A 120.0 . . ?
C1 N7 H7B 120.0 . . ?
N9 N8 C1 119.2(3) . . ?
C2 N8 N9 109.6(3) . . ?
C2 N8 C1 131.2(3) . . ?
C3 N9 N8 101.3(3) . . ?
C2 N10 C3 103.0(3) . . ?
N6 C1 N7 124.7(3) . . ?
N6 C1 N8 117.1(3) . . ?
N7 C1 N8 118.2(3) . . ?
N8 C2 H2 124.9 . . ?
N10 C2 N8 110.3(3) . . ?
N10 C2 H2 124.9 . . ?
N9 C3 N10 115.8(3) . . ?
N9 C3 H3 122.1 . . ?
N10 C3 H3 122.1 . . ?
N5 N1 N2 107.8(3) . . ?
N3 N2 N1 107.9(3) . . ?
N4 N3 N2 108.1(3) . . ?
N3 N4 N5 108.2(3) . . ?
N1 N5 N4 108.1(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
N8 N9 C3 N10 0.3(4) . . . . ?
N9 N8 C1 N6 10.0(4) . . . . ?
N9 N8 C1 N7 -170.0(3) . . . . ?
N9 N8 C2 N10 -0.3(4) . . . . ?
C1 N8 N9 C3 -177.6(3) . . . . ?
C1 N8 C2 N10 176.9(3) . . . . ?
C2 N8 N9 C3 0.0(4) . . . . ?
C2 N8 C1 N6 -167.0(3) . . . . ?
C2 N8 C1 N7 13.1(5) . . . . ?
C2 N10 C3 N9 -0.4(5) . . . . ?
C3 N10 C2 N8 0.4(4) . . . . ?
N1 N2 N3 N4 0.4(4) . . . . ?
N2 N1 N5 N4 0.2(4) . . . . ?
N2 N3 N4 N5 -0.2(4) . . . . ?
N3 N4 N5 N1 0.0(4) . . . . ?
N5 N1 N2 N3 -0.3(4) . . . . ?

_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_WPF240422_3
_database_code_depnum_ccdc_archive 'CCDC 2322438'
loop_
_audit_author_name
_audit_author_address
'Pengfei Wang'
;University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 N2, N5'
_chemical_formula_sum            'C7 H9 N7'
_chemical_formula_weight         191.21

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'

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

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

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

_cell_length_a                   3.9161(5)
_cell_length_b                   9.7152(11)
_cell_length_c                   12.5718(14)
_cell_angle_alpha                84.813(3)
_cell_angle_beta                 86.135(4)
_cell_angle_gamma                83.993(4)
_cell_volume                     472.92(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3950
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      27.13

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5830
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            2115
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.115
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2115
_reflns_number_gt                1409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+0.0683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2115
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4293(5) 0.23208(16) 0.72294(13) 0.0363(4) Uani 1 1 d . . . . .
C2 C 0.3947(6) 0.34996(18) 0.65163(14) 0.0494(5) Uani 1 1 d . . . . .
H2 H 0.440628 0.435534 0.671973 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2916(6) 0.3385(2) 0.55061(16) 0.0618(6) Uani 1 1 d . . . . .
H3 H 0.270214 0.417080 0.502529 0.074 Uiso 1 1 calc R U . . .
C4 C 0.2197(6) 0.2134(3) 0.51945(17) 0.0633(6) Uani 1 1 d . . . . .
H4 H 0.150503 0.207280 0.450852 0.076 Uiso 1 1 calc R U . . .
C5 C 0.2505(6) 0.0982(2) 0.58990(16) 0.0570(6) Uani 1 1 d . . . . .
H5 H 0.199829 0.013338 0.569384 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3552(5) 0.10648(18) 0.69038(15) 0.0448(5) Uani 1 1 d . . . . .
H6 H 0.377045 0.026961 0.737475 0.054 Uiso 1 1 calc R U . . .
C7 C 0.5450(5) 0.24021(16) 0.83056(13) 0.0383(5) Uani 1 1 d . . . . .
N1 N 0.1224(5) 0.63037(16) 0.82235(14) 0.0625(6) Uani 1 1 d . . . . .
N2 N 0.1751(5) 0.67386(16) 0.91297(13) 0.0605(5) Uani 1 1 d . . . . .
N3 N 0.0547(5) 0.80390(16) 0.91269(13) 0.0589(5) Uani 1 1 d . . . . .
N4 N -0.0741(5) 0.84171(15) 0.82215(14) 0.0574(5) Uani 1 1 d . . . . .
N5 N -0.0331(6) 0.73456(18) 0.76388(14) 0.0673(6) Uani 1 1 d . . . . .
N6 N 0.5037(5) 0.35794(14) 0.87476(12) 0.0552(5) Uani 1 1 d . . . . .
H6A H 0.571721 0.362195 0.937902 0.066 Uiso 1 1 calc R U . . .
H6B H 0.408390 0.431174 0.840709 0.066 Uiso 1 1 calc R U . . .
N7 N 0.6901(5) 0.12885(14) 0.88252(11) 0.0491(5) Uani 1 1 d . . . . .
H7A H 0.758052 0.133245 0.945654 0.059 Uiso 1 1 calc R U . . .
H7B H 0.717487 0.051301 0.853516 0.059 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(2) . ?
C1 C2 1.390(2) . ?
C1 C7 1.467(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N6 1.307(2) . ?
C7 N7 1.309(2) . ?
N1 N2 1.287(2) . ?
N1 N5 1.316(2) . ?
N2 N3 1.301(2) . ?
N3 N4 1.284(2) . ?
N4 N5 1.316(2) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.89(17) . . ?
C6 C1 C7 120.54(15) . . ?
C2 C1 C7 120.57(16) . . ?
C3 C2 C1 119.20(19) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 121.25(19) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.47(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.74(18) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
N6 C7 N7 119.91(16) . . ?
N6 C7 C1 120.32(15) . . ?
N7 C7 C1 119.77(15) . . ?
N2 N1 N5 107.92(15) . . ?
N1 N2 N3 108.56(16) . . ?
N4 N3 N2 108.39(15) . . ?
N3 N4 N5 108.17(15) . . ?
N1 N5 N4 106.96(16) . . ?
C7 N6 H6A 120.0 . . ?
C7 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.7(3) . . . . ?
C7 C1 C2 C3 178.8(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C7 C1 C6 C5 -179.38(19) . . . . ?
C6 C1 C7 N6 -156.59(19) . . . . ?
C2 C1 C7 N6 23.9(3) . . . . ?
C6 C1 C7 N7 23.3(3) . . . . ?
C2 C1 C7 N7 -156.16(19) . . . . ?
N5 N1 N2 N3 0.1(3) . . . . ?
N1 N2 N3 N4 0.2(3) . . . . ?
N2 N3 N4 N5 -0.4(3) . . . . ?
N2 N1 N5 N4 -0.3(3) . . . . ?
N3 N4 N5 N1 0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7 H7A N3 0.86 2.13 2.973(2) 165.6 2_667 yes
N7 H7B N3 0.86 2.69 3.326(2) 132.2 1_645 yes
N7 H7B N4 0.86 2.17 2.993(2) 159.4 1_645 yes
N6 H6A N2 0.86 2.16 3.004(2) 165.5 2_667 yes
N6 H6B N2 0.86 2.65 3.265(2) 129.1 . yes
N6 H6B N1 0.86 2.13 2.942(2) 156.5 . yes

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2322441'
loop_
_audit_author_name
_audit_author_address
'Pengfei Wang'
;University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2021-11-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 N O2, N5'
_chemical_formula_sum            'C2 H6 N6 O2'
_chemical_formula_weight         146.13
_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      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                   5.2112(15)
_cell_length_b                   7.849(2)
_cell_length_c                   7.880(3)
_cell_angle_alpha                78.116(9)
_cell_angle_beta                 76.103(10)
_cell_angle_gamma                73.730(9)
_cell_volume                     297.01(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1803
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             152
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2455
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.693
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_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                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                942
_reflns_number_total             1030
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1030
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.080
_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)+(0.0438P)²+0.0602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0855
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
O1 O 0.30941(18) 0.59697(13) 0.28714(12) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.6989(3) 0.71841(19) 0.18390(18) 0.0265(3) Uani 1 1 d . . . . .
H1A H 0.681(3) 0.840(2) 0.141(2) 0.036(4) Uiso 1 1 d . . . . .
H1B H 0.859(3) 0.654(2) 0.118(2) 0.033(4) Uiso 1 1 d . . . . .
C2 C 0.4542(2) 0.66386(16) 0.16234(17) 0.0240(3) Uani 1 1 d . . . . .
O2 O 0.4046(2) 0.69503(13) 0.00151(13) 0.0328(3) Uani 1 1 d . . . . .
H2 H 0.530(5) 0.739(3) -0.079(3) 0.069(7) Uiso 1 1 d . . . . .
N6 N 0.7228(2) 0.68173(17) 0.37071(15) 0.0279(3) Uani 1 1 d . . . . .
H6A H 0.773(4) 0.564(3) 0.403(3) 0.063(6) Uiso 1 1 d . . . . .
H6B H 0.567(4) 0.727(2) 0.451(2) 0.046(5) Uiso 1 1 d . . . . .
H6C H 0.850(4) 0.732(2) 0.384(2) 0.047(5) Uiso 1 1 d . . . . .
N3 N -0.2243(2) 1.18211(15) 0.38113(15) 0.0328(3) Uani 1 1 d . . . . .
N4 N -0.1090(3) 1.02985(16) 0.31874(16) 0.0368(3) Uani 1 1 d . . . . .
N1 N 0.1664(2) 1.19821(16) 0.23089(15) 0.0326(3) Uani 1 1 d . . . . .
N2 N -0.0545(2) 1.28626(15) 0.32711(15) 0.0325(3) Uani 1 1 d . . . . .
N5 N 0.1324(3) 1.04041(16) 0.22560(16) 0.0391(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2103(16) . ?
C1 H1A 0.934(17) . ?
C1 H1B 0.938(16) . ?
C1 C2 1.5098(18) . ?
C1 N6 1.4692(18) . ?
C2 O2 1.3140(16) . ?
O2 H2 0.88(2) . ?
N6 H6A 0.89(2) . ?
N6 H6B 0.93(2) . ?
N6 H6C 0.895(19) . ?
N3 N4 1.3148(17) . ?
N3 N2 1.3089(17) . ?
N4 N5 1.3110(18) . ?
N1 N2 1.3146(17) . ?
N1 N5 1.3095(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
H1A C1 H1B 108.2(14) . . ?
C2 C1 H1A 109.3(10) . . ?
C2 C1 H1B 110.1(9) . . ?
N6 C1 H1A 110.2(9) . . ?
N6 C1 H1B 108.7(9) . . ?
N6 C1 C2 110.40(11) . . ?
O1 C2 C1 121.66(12) . . ?
O1 C2 O2 121.82(11) . . ?
O2 C2 C1 116.51(11) . . ?
C2 O2 H2 113.1(14) . . ?
C1 N6 H6A 109.1(13) . . ?
C1 N6 H6B 116.3(11) . . ?
C1 N6 H6C 109.5(12) . . ?
H6A N6 H6B 107.8(17) . . ?
H6A N6 H6C 108.9(18) . . ?
H6B N6 H6C 105.0(16) . . ?
N2 N3 N4 108.25(11) . . ?
N5 N4 N3 107.83(11) . . ?
N5 N1 N2 108.24(12) . . ?
N3 N2 N1 107.68(11) . . ?
N1 N5 N4 108.00(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
N6 C1 C2 O1 -1.21(17) . . . . ?
N6 C1 C2 O2 177.91(11) . . . . ?
N3 N4 N5 N1 0.18(15) . . . . ?
N4 N3 N2 N1 0.04(14) . . . . ?
N2 N3 N4 N5 -0.14(15) . . . . ?
N2 N1 N5 N4 -0.15(15) . . . . ?
N5 N1 N2 N3 0.07(15) . . . . ?

_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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2322436'
loop_
_audit_author_name
_audit_author_address
'Pengfei Wang'
;University
China
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'N5, C2 H7 N2'
_chemical_formula_sum            'C2 H7 N7'
_chemical_formula_weight         129.125
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z+1/2
3 -x,y+1/2,-z
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z-1/2
7 x,-y-1/2,z
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      62
_cell_length_a                   13.629(1)
_cell_length_b                   6.5997(6)
_cell_length_c                   7.4672(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     671.65(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2345
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.52
_cell_measurement_theta_min      3.11
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1032 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.9072.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      .
_exptl_crystal_description       plate
_exptl_crystal_F_000             272.210
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.9955
_diffrn_reflns_Laue_measured_fraction_max 0.9941
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5669
_diffrn_reflns_point_group_measured_fraction_full 0.9955
_diffrn_reflns_point_group_measured_fraction_max 0.9941
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.11
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9955
_diffrn_measured_fraction_theta_max 0.9941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                594
_reflns_number_total             836
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.2161
_refine_diff_density_min         -0.2229
_refine_diff_density_rms         0.0507
_refine_ls_d_res_high            0.7710
_refine_ls_d_res_low             6.5487
_refine_ls_goodness_of_fit_ref   1.0424
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     62
_refine_ls_number_reflns         836
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.0424
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²+0.0994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1230
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a X=CH2 refined with riding coordinates:
 N6(H6a,H6b), N7(H7a,H7b)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N 0.35411(12) 0.75 0.6122(2) 0.0530(5) Uani 1.000000 2 S T P
N2 N 0.37546(13) 0.75 0.7835(2) 0.0583(5) Uani 1.000000 2 S T P
N3 N 0.29337(13) 0.75 0.8717(2) 0.0599(5) Uani 1.000000 2 S T P
N4 N 0.22098(12) 0.75 0.7561(2) 0.0629(6) Uani 1.000000 2 S T P
N5 N 0.25907(13) 0.75 0.5951(2) 0.0563(5) Uani 1.000000 2 S T P
C1 C 0.5179(2) 0.75 0.1648(4) 0.0732(8) Uani 1.000000 2 S T P
H1a H 0.550(2) 0.75 0.061(5) 0.102(11) Uiso 1.000000 2 S T P
H1b H 0.4796(18) 0.863(5) 0.166(4) 0.162(12) Uiso 1.000000 1 . . .
C2 C 0.58938(14) 0.75 0.3149(2) 0.0439(5) Uani 1.000000 2 S T P
N6 N 0.68293(11) 0.75 0.2792(2) 0.0484(5) Uani 1.000000 2 S T P
H6a H 0.70266(11) 0.7500000000000001 0.1698(2) 0.0580(6) Uiso 1.000000 2 RS T P
H6b H 0.72497(11) 0.75 0.3651(2) 0.0580(6) Uiso 1.000000 2 RS T P
N7 N 0.55704(12) 0.75 0.4783(2) 0.0530(5) Uani 1.000000 2 S T P
H7a H 0.49493(12) 0.7500000000000003 0.4986(2) 0.0636(6) Uiso 1.000000 2 RS T P
H7b H 0.59772(12) 0.7500000000000001 0.5663(2) 0.0636(6) Uiso 1.000000 2 RS T P


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
N1 N2 1.312(2) . ?
N1 N5 1.302(2) . ?
N2 N3 1.298(2) . ?
N3 N4 1.311(2) . ?
N4 N5 1.309(2) . ?
C1 H1a 0.89(4) . ?
C1 H1b 0.91(3) . ?
C1 H1b 0.91(3) 7_575 ?
C1 C2 1.485(3) . ?
C2 N6 1.302(2) . ?
C2 N7 1.297(2) . ?
N6 H6a 0.8600 . ?
N6 H6b 0.8600 . ?
N7 H7a 0.8600 . ?
N7 H7b 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 N1 N2 108.43(15) . . ?
N3 N2 N1 107.67(16) . . ?
N4 N3 N2 108.33(16) . . ?
N5 N4 N3 107.83(16) . . ?
N4 N5 N1 107.74(15) . . ?
H1b C1 H1a 107(2) . . ?
H1b C1 H1a 107(2) 7_575 . ?
H1b C1 H1b 110(4) 7_575 . ?
C2 C1 H1a 110(2) . . ?
C2 C1 H1b 111.7(18) . . ?
C2 C1 H1b 111.7(18) . 7_575 ?
N6 C2 C1 119.2(2) . . ?
N7 C2 C1 119.1(2) . . ?
N7 C2 N6 121.64(17) . . ?
H6a N6 C2 120.0 . . ?
H6b N6 C2 120.0 . . ?
H6b N6 H6a 120.0 . . ?
H7a N7 C2 120.0 . . ?
H7b N7 C2 120.0 . . ?
H7b N7 H7a 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 N4 0.0 . . . . ?
N1 N5 N4 N3 0.0 . . . . ?
N2 N3 N4 N5 0.0 . . . . ?


_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_1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2322437'
loop_
_audit_author_name
_audit_author_address
'Pengfei Wang'
;University
China
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2024-04-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'N5, C4 H9 N2'
_chemical_formula_sum            'C4 H9 N7'
_chemical_formula_weight         155.163
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z
3 -x,-y,-z
4 x,-y-1/2,z

_symmetry_Int_Tables_number      11
_cell_length_a                   7.0037(15)
_cell_length_b                   7.0175(15)
_cell_length_c                   7.7191(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.937(7)
_cell_angle_gamma                90
_cell_volume                     376.60(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1649
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.93
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             164.119
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.1434
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.9932
_diffrn_reflns_Laue_measured_fraction_max 0.9932
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5041
_diffrn_reflns_point_group_measured_fraction_full 0.9932
_diffrn_reflns_point_group_measured_fraction_max 0.9932
_diffrn_reflns_theta_full        25.0612
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.66
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9932
_diffrn_measured_fraction_theta_max 0.9932
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                534
_reflns_number_total             727
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.3529
_refine_diff_density_min         -0.3679
_refine_diff_density_rms         0.0911
_refine_ls_d_res_high            0.8389
_refine_ls_d_res_low             7.6626
_refine_ls_goodness_of_fit_ref   1.0564
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     87
_refine_ls_number_reflns         727
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.0556
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.2293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1406
_olex2_refinement_description    
;
1. Restrained distances
 N6-H6b
 0.88 with sigma of 0.01
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N 0.4481(4) 0.25 0.7729(5) 0.0495(9) Uani 1.000000 2 S T P
N2 N 0.5808(5) 0.25 0.9079(4) 0.0483(9) Uani 1.000000 2 S T P
N3 N 0.7484(4) 0.25 0.8511(4) 0.0437(9) Uani 1.000000 2 S T P
N4 N 0.7229(5) 0.25 0.6811(4) 0.0493(9) Uani 1.000000 2 S T P
N5 N 0.5366(5) 0.25 0.6323(4) 0.0490(9) Uani 1.000000 2 S T P
H7a H 0.234(5) 0.25 -0.062(5) 0.046(10) Uiso 1.000000 2 S T P
N6 N 0.3977(4) 0.25 0.2465(4) 0.0410(9) Uani 1.000000 2 DS T P
N7 N 0.1486(5) 0.25 0.0282(4) 0.0361(8) Uani 1.000000 2 S T P
H7b H 0.030(6) 0.25 0.006(5) 0.034(11) Uiso 1.000000 2 S T P
C1 C 0.2124(5) 0.25 0.1959(4) 0.0279(8) Uani 1.000000 2 S T P
C2 C 0.0808(5) 0.25 0.3279(5) 0.0339(9) Uani 1.000000 2 S T P
H2 H 0.139(5) 0.25 0.435(5) 0.038(10) Uiso 1.000000 2 S T P
C3 C -0.1081(4) 0.1455(4) 0.2966(4) 0.0390(7) Uani 1.000000 1 . . .
H3a H -0.155(3) 0.083(4) 0.399(3) 0.043(7) Uiso 1.000000 1 . . .
H3b H -0.125(3) 0.075(4) 0.189(4) 0.049(8) Uiso 1.000000 1 . . .
H6a H 0.481(5) 0.25 0.164(5) 0.044(11) Uiso 1.000000 2 S T P
H6b H 0.438(5) 0.25 0.3584(17) 0.061(13) Uiso 1.000000 2 DS T P


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
N1 N2 1.310(4) . ?
N1 N5 1.313(4) . ?
N2 N3 1.302(4) . ?
N3 N4 1.303(4) . ?
N4 N5 1.314(4) . ?
H7a N7 0.97(4) . ?
N6 C1 1.309(4) . ?
N6 H6a 0.92(4) . ?
N6 H6b 0.876(10) . ?
N7 H7b 0.83(4) . ?
N7 C1 1.317(4) . ?
C1 C2 1.454(5) . ?
C2 H2 0.88(4) . ?
C2 C3 1.507(4) 4_565 ?
C2 C3 1.507(4) . ?
C3 C3 1.467(6) 4_565 ?
C3 H3a 1.00(3) . ?
C3 H3b 0.96(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
N5 N1 N2 107.3(3) . . ?
N3 N2 N1 108.3(3) . . ?
N4 N3 N2 108.6(3) . . ?
N5 N4 N3 107.4(3) . . ?
N4 N5 N1 108.3(3) . . ?
H6a N6 C1 119(2) . . ?
H6b N6 C1 119(3) . . ?
H6b N6 H6a 122(4) . . ?
H7b N7 H7a 123(3) . . ?
C1 N7 H7a 123(2) . . ?
C1 N7 H7b 115(3) . . ?
N7 C1 N6 120.0(3) . . ?
C2 C1 N6 118.7(3) . . ?
C2 C1 N7 121.3(3) . . ?
H2 C2 C1 114(2) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 C1 120.4(3) 4_565 . ?
C3 C2 H2 116.8(19) . . ?
C3 C2 H2 116.8(19) 4_565 . ?
C3 C2 C3 58.3(2) 4_565 . ?
C3 C3 C2 60.86(12) 4_565 . ?
H3a C3 C2 117.1(14) . . ?
H3b C3 C2 113.7(15) . . ?
H3b C3 H3a 116(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 N4 -0.0 . . . . ?
N1 N5 N4 N3 -0.0 . . . . ?
N2 N3 N4 N5 0.0 . . . . ?
N6 C1 C2 C3 -145.62(13) . . . . ?
N6 C1 C2 C3 145.62(13) . . . 4_565 ?
N7 C1 C2 C3 34.38(13) . . . . ?
N7 C1 C2 C3 -34.38(13) . . . 4_565 ?
C1 C2 C3 C3 -109.1(2) . . . 4_565 ?
C1 C2 C3 C3 109.1(2) . . 4_565 . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
N6 H6b 1 0.8800 0.0100 0.0037

