# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2103623'
loop_
_audit_author_name
_audit_author_address
'Zihao Zhao'
;School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H4 N4'
_chemical_formula_sum            'C2 H4 N4'
_chemical_formula_weight         84.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.9827(5)
_cell_length_b                   4.49690(10)
_cell_length_c                   13.1144(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.3610(10)
_cell_angle_gamma                90
_cell_volume                     798.44(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2848
_cell_measurement_theta_min      6.54
_cell_measurement_theta_max      68.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   0.6553
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.876
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3685
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.539
_diffrn_reflns_theta_max         68.269
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             709
_reflns_number_gt                662
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0537P)²+0.3679P] 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         709
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
N1 N 0.33591(9) 0.4938(3) 0.62717(10) 0.0522(4) Uani 1 1 d . . . . .
C1 C 0.36823(9) 0.6075(3) 0.57127(10) 0.0364(4) Uani 1 1 d . . . . .
N2 N 0.40918(8) 0.7501(3) 0.51501(8) 0.0369(3) Uani 1 1 d . . . . .
C2 C 0.38479(8) 0.6703(3) 0.40823(10) 0.0297(3) Uani 1 1 d . . . . .
N3 N 0.31882(8) 0.4606(3) 0.35376(9) 0.0391(3) Uani 1 1 d . . . . .
H3A H 0.305241 0.420678 0.284531 0.047 Uiso 1 1 calc R U . . .
H3B H 0.289775 0.365033 0.387787 0.047 Uiso 1 1 calc R U . . .
N4 N 0.42827(8) 0.8136(3) 0.35341(9) 0.0389(4) Uani 1 1 d . . . . .
H4A H 0.413638 0.770234 0.284190 0.047 Uiso 1 1 calc R U . . .
H4B H 0.471114 0.949823 0.387068 0.047 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0554(7) 0.0704(9) 0.0384(7) 0.0086(6) 0.0273(6) -0.0006(6)
C1 0.0357(7) 0.0461(8) 0.0267(6) -0.0001(5) 0.0128(5) 0.0016(5)
N2 0.0390(6) 0.0452(7) 0.0281(6) -0.0020(4) 0.0161(5) -0.0064(5)
C2 0.0296(6) 0.0316(6) 0.0290(6) 0.0013(4) 0.0134(5) 0.0041(4)
N3 0.0448(6) 0.0425(6) 0.0343(6) -0.0063(5) 0.0210(5) -0.0101(5)
N4 0.0453(6) 0.0445(7) 0.0308(6) -0.0028(4) 0.0200(5) -0.0100(5)

_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
N1 C1 1.1567(17) . ?
C1 N2 1.3113(16) . ?
N2 C2 1.3360(16) . ?
C2 N4 1.3257(15) . ?
C2 N3 1.3311(16) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 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
N1 C1 N2 175.32(14) . . ?
C1 N2 C2 118.33(11) . . ?
N4 C2 N3 118.53(11) . . ?
N4 C2 N2 117.42(11) . . ?
N3 C2 N2 124.04(11) . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 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
C1 N2 C2 N4 -178.85(11) . . . . ?
C1 N2 C2 N3 2.27(19) . . . . ?

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.030

_shelx_res_file                  
;
TITL a_a.res in C2/c
    a_a.res
    created by SHELXL-2016/6 at 17:23:07 on 23-May-2018
REM Old TITL a in C2/c
REM SHELXT solution in C2/c
REM R1 0.113,  Rweak 0.001,  Alpha 0.025,  Orientation as input
REM Formula found by SHELXT:  C N2
CELL  1.54178  14.9827   4.4969  13.1144   90.000  115.361   90.000
ZERR   8.000   0.0005   0.0001   0.0004    0.000    0.001    0.000
LATT  7
SYMM -X, Y, 1/2-Z
SFAC C H N
UNIT 16 32 32
ACTA
TEMP 23.460
size 0.20 0.20 0.20
conf
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
WGHT    0.053700    0.367900
FVAR       1.62690
N1    3    0.335907    0.493779    0.627171    11.00000    0.05536    0.07037 =
         0.03842    0.00858    0.02733   -0.00062
C1    1    0.368234    0.607546    0.571265    11.00000    0.03570    0.04611 =
         0.02674   -0.00009    0.01284    0.00157
N2    3    0.409184    0.750108    0.515008    11.00000    0.03903    0.04525 =
         0.02806   -0.00204    0.01606   -0.00643
C2    1    0.384794    0.670293    0.408234    11.00000    0.02959    0.03157 =
         0.02898    0.00132    0.01340    0.00414
N3    3    0.318821    0.460597    0.353758    11.00000    0.04480    0.04245 =
         0.03430   -0.00634    0.02098   -0.01010
AFIX  93
H3A   2    0.305241    0.420678    0.284531    11.00000   -1.20000
H3B   2    0.289775    0.365033    0.387787    11.00000   -1.20000
AFIX   0
N4    3    0.428274    0.813560    0.353411    11.00000    0.04531    0.04445 =
         0.03076   -0.00277    0.01995   -0.01003
AFIX  93
H4A   2    0.413638    0.770234    0.284190    11.00000   -1.20000
H4B   2    0.471114    0.949823    0.387068    11.00000   -1.20000
AFIX   0
HKLF 4




REM  a_a.res in C2/c
REM R1 =  0.0329 for     662 Fo > 4sig(Fo)  and  0.0346 for all     709 data
REM     55 parameters refined using      0 restraints

END

WGHT      0.0523      0.3737

REM Highest difference peak  0.119,  deepest hole -0.145,  1-sigma level  0.030
Q1    1   0.3384  0.3336  0.3051  11.00000  0.05    0.12
Q2    1   0.4510  0.8854  0.5429  11.00000  0.05    0.12
Q3    1   0.4150  0.6581  0.4812  11.00000  0.05    0.10
Q4    1   0.3829  0.7706  0.4598  11.00000  0.05    0.10
Q5    1   0.4302  0.6630  0.3940  11.00000  0.05    0.10
Q6    1   0.3747  0.6394  0.6473  11.00000  0.05    0.09
Q7    1   0.3787  0.8216  0.3601  11.00000  0.05    0.09
Q8    1   0.3087  0.4049  0.6825  11.00000  0.05    0.09
Q9    1   0.3718  0.7658  0.5194  11.00000  0.05    0.07
Q10   1   0.3995  0.5732  0.2334  11.00000  0.05    0.06
Q11   1   0.3742  0.5467  0.3944  11.00000  0.05    0.06
Q12   1   0.2619  0.6271  0.2699  11.00000  0.05    0.06
Q13   1   0.3329  0.2656  0.4041  11.00000  0.05    0.06
Q14   1   0.3564  0.2172  0.3757  11.00000  0.05    0.06
Q15   1   0.4475  0.6260  0.3245  11.00000  0.05    0.05
Q16   1   0.3518  0.3984  0.6013  11.00000  0.05    0.05
Q17   1   0.5068  0.8607  0.4193  11.00000  0.05    0.05
Q18   1   0.3027  0.6586  0.6823  11.00000  0.05    0.05
Q19   1   0.5014  0.6667  0.3871  11.00000  0.05    0.05
Q20   1   0.2531  0.6500  0.3420  11.00000  0.05    0.05
;
_shelx_res_checksum              65157
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2103625'
loop_
_audit_author_name
_audit_author_address
'Zihao Zhao'
;School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N3 O2'
_chemical_formula_sum            'C3 H7 N3 O2'
_chemical_formula_weight         117.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   4.9399(2)
_cell_length_b                   6.0035(3)
_cell_length_c                   17.1666(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.272(2)
_cell_angle_gamma                90
_cell_volume                     507.69(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4569
_cell_measurement_theta_min      5.17
_cell_measurement_theta_max      68.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   0.6969
_exptl_transmission_factor_max   0.7530
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.104
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6316
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.167
_diffrn_reflns_theta_max         68.082
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             921
_reflns_number_gt                855
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0742P)²+0.1832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         921
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.236
_refine_ls_restrained_S_all      1.236
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1065(3) 0.4574(2) 0.67940(8) 0.0422(5) Uani 1 1 d . . . . .
H1 H 0.004823 0.352167 0.685910 0.063 Uiso 1 1 calc R U . . .
C1 C 0.6431(3) 0.9444(3) 0.63883(9) 0.0259(4) Uani 1 1 d . . . . .
N1 N 0.7827(3) 0.9490(3) 0.57650(9) 0.0360(5) Uani 1 1 d . . . . .
H1A H 0.902786 1.050810 0.571686 0.043 Uiso 1 1 calc R U . . .
H1B H 0.753999 0.850090 0.540589 0.043 Uiso 1 1 calc R U . . .
O2 O 0.1530(3) 0.2883(2) 0.56565(8) 0.0457(5) Uani 1 1 d . . . . .
C2 C 0.4077(4) 0.6107(3) 0.59047(10) 0.0301(5) Uani 1 1 d . . . . .
H2A H 0.577417 0.536273 0.582129 0.036 Uiso 1 1 calc R U . . .
H2AB H 0.340122 0.676756 0.541235 0.036 Uiso 1 1 calc R U . . .
N2 N 0.6904(4) 1.0983(3) 0.69350(10) 0.0383(5) Uani 1 1 d . . . . .
N3 N 0.4592(3) 0.7860(2) 0.64759(9) 0.0293(4) Uani 1 1 d . . . . .
H3 H 0.620(6) 1.080(4) 0.7281(15) 0.038(7) Uiso 1 1 d . . . . .
H2 H 0.378(5) 0.787(4) 0.6894(16) 0.046(7) Uiso 1 1 d . . . . .
C3 C 0.2040(4) 0.4388(3) 0.61479(10) 0.0292(5) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0507(9) 0.0371(8) 0.0422(8) -0.0092(6) 0.0267(7) -0.0192(6)
C1 0.0280(9) 0.0253(9) 0.0247(9) 0.0006(6) 0.0033(6) -0.0057(6)
N1 0.0420(9) 0.0358(9) 0.0320(9) -0.0074(6) 0.0146(7) -0.0206(7)
O2 0.0574(10) 0.0418(8) 0.0406(8) -0.0156(6) 0.0219(6) -0.0291(7)
C2 0.0347(9) 0.0289(9) 0.0277(9) -0.0053(7) 0.0095(7) -0.0109(7)
N2 0.0486(10) 0.0396(9) 0.0285(9) -0.0080(7) 0.0145(7) -0.0193(7)
N3 0.0336(8) 0.0287(8) 0.0269(8) -0.0035(6) 0.0112(6) -0.0120(6)
C3 0.0315(9) 0.0271(9) 0.0301(9) -0.0032(7) 0.0101(7) -0.0081(7)

_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 C3 1.247(2) . ?
C1 N1 1.316(2) . ?
C1 N2 1.325(2) . ?
C1 N3 1.331(2) . ?
O2 C3 1.249(2) . ?
C2 N3 1.448(2) . ?
C2 C3 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
N1 C1 N2 119.06(16) . . ?
N1 C1 N3 120.67(15) . . ?
N2 C1 N3 120.26(16) . . ?
N3 C2 C3 113.18(14) . . ?
C1 N3 C2 121.98(15) . . ?
O1 C3 O2 126.42(16) . . ?
O1 C3 C2 119.39(15) . . ?
O2 C3 C2 114.20(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
N1 C1 N3 C2 1.1(3) . . . . ?
N2 C1 N3 C2 -177.94(18) . . . . ?
C3 C2 N3 C1 176.02(16) . . . . ?
N3 C2 C3 O1 -1.6(3) . . . . ?
N3 C2 C3 O2 178.76(17) . . . . ?

_refine_diff_density_max         0.663
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.067

_shelx_res_file                  
;
TITL a_a.res in P2(1)/n
    a_a.res
    created by SHELXL-2018/3 at 18:20:33 on 26-Mar-2021
REM Old TITL a in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.173, Rweak 0.005, Alpha 0.018
REM <I/s>   1.702 for   98 systematic absences,  Orientation as input
REM Formula found by SHELXT:  C3 N2 O3
CELL  1.54178   4.9399   6.0035  17.1666   90.000   94.272   90.000
ZERR    4.000   0.0002   0.0003   0.0008    0.000    0.002    0.000
LATT  1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C H N O
UNIT 12 28 12 8
ACTA
size 0.22 0.20 0.18
conf
TEMP 21.850
L.S. 10
BOND
LIST 6
FMAP 2
PLAN 20
WGHT    0.074200    0.183200
FVAR       1.07535
O1    4    0.106496    0.457423    0.679403    11.00000    0.05070    0.03711 =
         0.04220   -0.00918    0.02671   -0.01922
AFIX 147
H1    2    0.004823    0.352167    0.685910    11.00000   -1.50000
AFIX   0
C1    1    0.643058    0.944423    0.638834    11.00000    0.02796    0.02527 =
         0.02465    0.00063    0.00326   -0.00574
N1    3    0.782749    0.948966    0.576504    11.00000    0.04202    0.03582 =
         0.03199   -0.00745    0.01462   -0.02064
AFIX  93
H1A   2    0.902786    1.050810    0.571686    11.00000   -1.20000
H1B   2    0.753999    0.850090    0.540589    11.00000   -1.20000
AFIX   0
O2    4    0.152955    0.288283    0.565649    11.00000    0.05740    0.04181 =
         0.04063   -0.01555    0.02187   -0.02911
C2    1    0.407707    0.610709    0.590466    11.00000    0.03472    0.02892 =
         0.02773   -0.00530    0.00952   -0.01093
AFIX  23
H2A   2    0.577417    0.536273    0.582129    11.00000   -1.20000
H2AB  2    0.340122    0.676756    0.541235    11.00000   -1.20000
AFIX   0
N2    3    0.690434    1.098287    0.693503    11.00000    0.04864    0.03958 =
         0.02852   -0.00797    0.01452   -0.01927
N3    3    0.459201    0.786027    0.647593    11.00000    0.03362    0.02872 =
         0.02686   -0.00353    0.01122   -0.01202
H3    2    0.620355    1.079999    0.728149    11.00000    0.03821
H2    2    0.378432    0.787434    0.689409    11.00000    0.04575
C3    1    0.204005    0.438824    0.614787    11.00000    0.03154    0.02710 =
         0.03014   -0.00323    0.01009   -0.00813
HKLF 4




REM  a_a.res in P2(1)/n
REM wR2 = 0.138682, GooF = S = 1.23587, Restrained GooF = 1.23587 for all data
REM R1 = 0.047709 for 855 Fo > 4sig(Fo) and 0.051679 for all 921 data
REM 82 parameters refined using 0 restraints

END

WGHT      0.0944      0.2181

REM Highest difference peak  0.663,  deepest hole -0.448,  1-sigma level  0.067
Q1    1   0.8085  1.2085  0.6839  11.00000  0.05    0.66
Q2    1   0.0488  0.3782  0.5614  11.00000  0.05    0.19
Q3    1   0.5286  1.1429  0.7384  11.00000  0.05    0.14
Q4    1   0.8217  0.4091  0.5773  11.00000  0.05    0.14
Q5    1   0.2462  0.5231  0.7038  11.00000  0.05    0.14
Q6    1   0.6685  0.4542  0.6146  11.00000  0.05    0.13
Q7    1   0.4614  0.6225  0.5405  11.00000  0.05    0.12
Q8    1   0.2029  0.7456  0.5358  11.00000  0.05    0.12
Q9    1   0.1507  0.5713  0.4747  11.00000  0.05    0.12
Q10   1   0.2760  0.9374  0.6861  11.00000  0.05    0.11
Q11   1   0.0982  0.9358  0.7023  11.00000  0.05    0.11
Q12   1   0.4522  0.6980  0.6227  11.00000  0.05    0.11
Q13   1   0.5400  0.8794  0.6373  11.00000  0.05    0.11
Q14   1   0.3094  0.5282  0.5994  11.00000  0.05    0.11
Q15   1   0.2817  0.4471  0.7497  11.00000  0.05    0.10
Q16   1   0.7918  1.0750  0.5605  11.00000  0.05    0.09
Q17   1   0.6372  0.9284  0.4590  11.00000  0.05    0.09
Q18   1   0.7870  1.0630  0.7993  11.00000  0.05    0.09
Q19   1   1.0201  0.9372  0.7411  11.00000  0.05    0.09
Q20   1   0.3675  0.7791  0.6121  11.00000  0.05    0.09
;
_shelx_res_checksum              48632
