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

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

data_ZJX_wg2_a
_database_code_depnum_ccdc_archive 'CCDC 2194173'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N2 O2, 2(N5), 2(H5 N2)'
_chemical_formula_sum            'C4 H14 N16 O2'
_chemical_formula_weight         318.31

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

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

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

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

_cell_length_a                   6.6303(4)
_cell_length_b                   7.8338(5)
_cell_length_c                   7.9449(5)
_cell_angle_alpha                117.137(2)
_cell_angle_beta                 93.126(2)
_cell_angle_gamma                111.674(2)
_cell_volume                     328.63(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3091
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             166
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6854
_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            5080
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.992
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1519
_reflns_number_gt                1265
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0755P)²+0.1294P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1519
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.5556(3) 0.6899(3) 0.0114(2) 0.0334(4) Uani 1 1 d . . . . .
H1 H 0.593388 0.820127 0.018389 0.040 Uiso 1 1 calc R U . . .
C2 C 0.4121(3) 0.5043(3) -0.1542(2) 0.0327(4) Uani 1 1 d . . . . .
H2 H 0.351904 0.508401 -0.260013 0.039 Uiso 1 1 calc R U . . .
N6 N 0.6439(2) 0.6852(2) 0.16652(19) 0.0315(4) Uani 1 1 d . . . . .
O1 O 0.7836(2) 0.8634(2) 0.32439(18) 0.0477(4) Uani 1 1 d . . . . .
N1 N 0.1406(3) 0.5750(3) 0.2534(2) 0.0404(4) Uani 1 1 d . . . . .
N2 N 0.0178(3) 0.3695(3) 0.1368(2) 0.0421(4) Uani 1 1 d . . . . .
N3 N 0.0564(3) 0.2724(3) 0.2245(3) 0.0454(4) Uani 1 1 d . . . . .
N4 N 0.2030(3) 0.4191(3) 0.3950(2) 0.0453(4) Uani 1 1 d . . . . .
N5 N 0.2544(3) 0.6042(3) 0.4125(2) 0.0401(4) Uani 1 1 d . . . . .
N7 N 0.7823(2) 1.0096(2) 0.7100(2) 0.0338(4) Uani 1 1 d . . . . .
H7A H 0.839863 1.150550 0.761648 0.041 Uiso 1 1 d R U . . .
H7B H 0.761939 0.945759 0.580509 0.041 Uiso 1 1 d R U . . .
H7C H 0.876858 0.978875 0.761623 0.041 Uiso 1 1 d R U . . .
N8 N 0.5727(2) 0.9358(2) 0.7519(2) 0.0356(4) Uani 1 1 d . . . . .
H8A H 0.579025 1.022463 0.738009 0.043 Uiso 1 1 d R U . . .
H8B H 0.483438 0.826734 0.651006 0.043 Uiso 1 1 d 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
C1 0.0398(9) 0.0365(9) 0.0296(8) 0.0189(7) 0.0121(7) 0.0195(8)
C2 0.0343(8) 0.0442(10) 0.0263(8) 0.0209(7) 0.0093(6) 0.0200(8)
N6 0.0300(7) 0.0354(8) 0.0225(7) 0.0127(6) 0.0069(5) 0.0109(6)
O1 0.0462(8) 0.0422(8) 0.0251(6) 0.0089(6) 0.0018(5) 0.0029(6)
N1 0.0470(9) 0.0373(8) 0.0401(8) 0.0210(7) 0.0099(7) 0.0206(7)
N2 0.0437(9) 0.0395(9) 0.0334(8) 0.0135(7) 0.0021(7) 0.0169(7)
N3 0.0510(10) 0.0356(9) 0.0495(10) 0.0224(8) 0.0155(8) 0.0179(8)
N4 0.0483(10) 0.0547(10) 0.0427(9) 0.0316(8) 0.0115(7) 0.0239(8)
N5 0.0356(8) 0.0392(8) 0.0335(8) 0.0138(7) 0.0063(6) 0.0117(7)
N7 0.0375(8) 0.0272(7) 0.0293(7) 0.0106(6) 0.0060(6) 0.0126(6)
N8 0.0275(7) 0.0315(7) 0.0282(7) 0.0067(6) 0.0059(5) 0.0054(6)

_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 N6 1.357(2) . ?
C1 C2 1.359(2) . ?
C1 H1 0.9300 . ?
C2 N6 1.344(2) 2_665 ?
C2 H2 0.9300 . ?
N6 O1 1.3043(19) . ?
N1 N2 1.305(2) . ?
N1 N5 1.313(2) . ?
N2 N3 1.317(2) . ?
N3 N4 1.309(2) . ?
N4 N5 1.297(2) . ?
N7 N8 1.418(2) . ?
N7 H7A 0.8900 . ?
N7 H7B 0.8900 . ?
N7 H7C 0.8900 . ?
N7 H8A 1.4106 . ?
N8 H8A 0.7232 . ?
N8 H8B 0.8201 . ?

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
N6 C1 C2 120.01(16) . . ?
N6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
N6 C2 C1 120.67(16) 2_665 . ?
N6 C2 H2 119.7 2_665 . ?
C1 C2 H2 119.7 . . ?
O1 N6 C2 120.80(15) . 2_665 ?
O1 N6 C1 119.87(15) . . ?
C2 N6 C1 119.32(15) 2_665 . ?
N2 N1 N5 107.56(15) . . ?
N1 N2 N3 107.90(15) . . ?
N4 N3 N2 107.97(15) . . ?
N5 N4 N3 107.81(15) . . ?
N4 N5 N1 108.76(15) . . ?
N8 N7 H7A 109.4 . . ?
N8 N7 H7B 109.5 . . ?
H7A N7 H7B 109.5 . . ?
N8 N7 H7C 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?
N8 N7 H8A 29.6 . . ?
H7A N7 H8A 84.6 . . ?
H7B N7 H8A 104.6 . . ?
H7C N7 H8A 135.3 . . ?
N7 N8 H8A 74.6 . . ?
N7 N8 H8B 107.7 . . ?
H8A N8 H8B 104.8 . . ?

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 N6 -0.1(3) . . . 2_665 ?
C2 C1 N6 O1 179.21(15) . . . . ?
C2 C1 N6 C2 0.1(3) . . . 2_665 ?
N5 N1 N2 N3 -0.1(2) . . . . ?
N1 N2 N3 N4 0.1(2) . . . . ?
N2 N3 N4 N5 -0.1(2) . . . . ?
N3 N4 N5 N1 0.0(2) . . . . ?
N2 N1 N5 N4 0.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 N8 0.93 2.67 3.385(2) 134.2 1_554 yes
C1 H1 N8 0.93 2.61 3.138(2) 116.9 2_676 yes
C2 H2 N4 0.93 2.53 3.434(2) 162.8 1_554 yes
N7 H7A N1 0.89 2.16 2.971(2) 150.5 2_676 yes
N7 H7A N2 0.89 2.58 3.056(2) 114.0 1_666 yes
N7 H7B O1 0.89 1.87 2.7398(19) 166.9 . yes
N7 H7C N3 0.89 2.22 3.005(2) 147.1 2_666 yes
N7 H7C N4 0.89 2.59 3.111(2) 118.0 2_666 yes
N8 H8B N4 0.82 2.66 3.446(2) 161.4 . yes
N8 H8B N5 0.82 1.91 2.722(2) 169.9 . yes

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.053

_shelx_res_file                  
;
TITL ZJX_wg2_a.res in P-1
    ZJX_wg2_a.res
    created by SHELXL-2018/3 at 11:35:34 on 02-Aug-2022
CELL 0.71073 6.6303 7.8338 7.9449 117.137 93.126 111.674
ZERR 1.00 0.0004 0.0005 0.0005 0.002 0.002 0.002
LATT 1
SFAC H  N  O  C
UNIT 14  16  2  4
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN -5
size 0.21 0.15 0.12
CONF
omit -1  -2   2
EQIV $2 x, y, z-1
HTAB C1 N8_$2
EQIV $3 -x+1, -y+2, -z+1
HTAB C1 N8_$3
HTAB C2 N4_$2
HTAB N7 N1_$3
EQIV $4 x+1, y+1, z+1
HTAB N7 N2_$4
HTAB N7 O1
EQIV $5 -x+1, -y+1, -z+1
HTAB N7 N3_$5
HTAB N7 N4_$5
HTAB N8 N4
HTAB N8 N5
TEMP 23.000
WGHT    0.075500    0.129400
FVAR       2.45567
C1    4    0.555624    0.689884    0.011402    11.00000    0.03981    0.03647 =
         0.02959    0.01894    0.01206    0.01947
AFIX  43
H1    1    0.593388    0.820127    0.018389    11.00000   -1.20000
AFIX   0
C2    4    0.412063    0.504284   -0.154173    11.00000    0.03434    0.04416 =
         0.02627    0.02093    0.00934    0.01996
AFIX  43
H2    1    0.351904    0.508401   -0.260013    11.00000   -1.20000
AFIX   0
N6    2    0.643866    0.685197    0.166518    11.00000    0.02998    0.03538 =
         0.02250    0.01272    0.00691    0.01094
O1    3    0.783643    0.863412    0.324385    11.00000    0.04618    0.04216 =
         0.02511    0.00885    0.00183    0.00285
N1    2    0.140643    0.575002    0.253396    11.00000    0.04699    0.03728 =
         0.04014    0.02103    0.00987    0.02064
N2    2    0.017766    0.369467    0.136849    11.00000    0.04370    0.03946 =
         0.03338    0.01353    0.00208    0.01688
N3    2    0.056386    0.272425    0.224483    11.00000    0.05099    0.03557 =
         0.04952    0.02243    0.01553    0.01793
N4    2    0.202972    0.419134    0.395034    11.00000    0.04833    0.05474 =
         0.04269    0.03156    0.01148    0.02391
N5    2    0.254403    0.604208    0.412528    11.00000    0.03558    0.03925 =
         0.03353    0.01378    0.00628    0.01173
N7    2    0.782328    1.009554    0.709980    11.00000    0.03751    0.02719 =
         0.02925    0.01058    0.00596    0.01258
AFIX   3
H7A   1    0.839863    1.150550    0.761648    11.00000   -1.20000
H7B   1    0.761939    0.945759    0.580509    11.00000   -1.20000
H7C   1    0.876858    0.978875    0.761623    11.00000   -1.20000
AFIX   0
N8    2    0.572674    0.935771    0.751907    11.00000    0.02748    0.03148 =
         0.02820    0.00667    0.00586    0.00540
AFIX   3
H8A   1    0.579025    1.022463    0.738009    11.00000   -1.20000
H8B   1    0.483438    0.826734    0.651006    11.00000   -1.20000
AFIX   0
HKLF 4 1 1 0 0 0 1 0 0 0 1




REM  ZJX_wg2_a.res in P-1
REM wR2 = 0.141941, GooF = S = 1.07585, Restrained GooF = 1.07585 for all data
REM R1 = 0.049838 for 1265 Fo > 4sig(Fo) and 0.060115 for all 1519 data
REM 100 parameters refined using 0 restraints

END

WGHT      0.0751      0.1168

REM Highest difference peak  0.459,  deepest hole -0.347,  1-sigma level  0.053
Q1    1   0.3665  0.7326  0.8217  11.00000  0.05    0.14
Q2    1   0.8316  0.7791  0.3552  11.00000  0.05    0.14
Q3    1   0.2770  0.3192  0.4192  11.00000  0.05    0.14
Q4    1   0.0020  0.3071  0.0148  11.00000  0.05    0.13
Q5    1   0.4250  0.5923 -0.0184  11.00000  0.05    0.13
;
_shelx_res_checksum              74209
####################################################################### 
# 
# 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_ZJX_wg1_a
_database_code_depnum_ccdc_archive 'CCDC 2244576'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-02-25 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N2 O2'
_chemical_formula_sum            'C4 H4 N2 O2'
_chemical_formula_weight         112.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   3.7348(10)
_cell_length_b                   11.013(3)
_cell_length_c                   5.7044(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.470(10)
_cell_angle_gamma                90
_cell_volume                     233.13(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    710
_cell_measurement_theta_min      5.49
_cell_measurement_theta_max      27.61

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             116
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.993

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6150
_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            1148
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         5.495
_diffrn_reflns_theta_max         27.718
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             529
_reflns_number_gt                424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.0785P] 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         529
_refine_ls_number_parameters     37
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.9215(3) 0.63602(10) 0.8059(2) 0.0514(4) Uani 1 1 d . . . . .
N1 N 0.7153(3) 0.56993(11) 0.6577(2) 0.0360(4) Uani 1 1 d . . . . .
C1 C 0.6386(4) 0.45340(13) 0.7094(3) 0.0377(4) Uani 1 1 d . . . . .
H1 H 0.732654 0.420355 0.853265 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5741(4) 0.61563(14) 0.4466(3) 0.0393(4) Uani 1 1 d . . . . .
H2 H 0.623697 0.695481 0.408157 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
O1 0.0592(8) 0.0415(7) 0.0477(7) -0.0089(5) -0.0192(6) -0.0003(5)
N1 0.0391(7) 0.0342(6) 0.0327(6) -0.0035(5) -0.0044(5) 0.0040(5)
C1 0.0438(8) 0.0362(8) 0.0315(7) 0.0042(6) -0.0031(6) 0.0051(6)
C2 0.0458(9) 0.0328(7) 0.0374(8) 0.0046(6) -0.0032(6) 0.0028(6)

_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 N1 1.3003(15) . ?
N1 C1 1.3544(19) . ?
N1 C2 1.3560(18) . ?
C1 C2 1.357(2) 3_666 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?

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
O1 N1 C1 120.89(12) . . ?
O1 N1 C2 120.81(13) . . ?
C1 N1 C2 118.30(12) . . ?
N1 C1 C2 120.72(13) . 3_666 ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 3_666 . ?
N1 C2 C1 120.98(14) . 3_666 ?
N1 C2 H2 119.5 . . ?
C1 C2 H2 119.5 3_666 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 -179.40(13) . . . 3_666 ?
C2 N1 C1 C2 0.0(2) . . . 3_666 ?
O1 N1 C2 C1 179.40(13) . . . 3_666 ?
C1 N1 C2 C1 0.0(2) . . . 3_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O1 0.93 2.27 3.169(2) 161.6 4_575 yes
C1 H1 O1 0.93 2.30 3.2081(19) 167.0 3_767 yes

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034

_shelx_res_file                  
;
TITL ZJX_wg1_a.res in P2(1)/c
    ZJX_wg1_a.res
    created by SHELXL-2018/3 at 11:54:17 on 02-Aug-2022
CELL 0.71073 3.7348 11.0128 5.7044 90.000 96.470 90.000
ZERR 2.00 0.0010 0.0025 0.0014 0.000 0.010 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C  H  N  O
UNIT 8  8  4  4
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN -2
HTAB C2 O1_$2
EQIV $2 x, -y+3/2, z-1/2
HTAB C1 O1_$1
EQIV $1 -x+2, -y+1, -z+2
CONF
size 0.20 0.18 0.05
TEMP 23.000
WGHT    0.039000    0.078500
FVAR       4.78666
O1    4    0.921464    0.636024    0.805923    11.00000    0.05923    0.04155 =
         0.04769   -0.00886   -0.01920   -0.00034
N1    3    0.715266    0.569929    0.657736    11.00000    0.03909    0.03416 =
         0.03267   -0.00349   -0.00444    0.00401
C1    1    0.638559    0.453405    0.709351    11.00000    0.04379    0.03623 =
         0.03153    0.00424   -0.00314    0.00512
AFIX  43
H1    2    0.732654    0.420355    0.853265    11.00000   -1.20000
AFIX   0
C2    1    0.574067    0.615634    0.446618    11.00000    0.04577    0.03277 =
         0.03744    0.00455   -0.00324    0.00281
AFIX  43
H2    2    0.623697    0.695481    0.408157    11.00000   -1.20000
AFIX   0
HKLF 4 1 1 0 0 0 1 0 0 0 1




REM  ZJX_wg1_a.res in P2(1)/c
REM wR2 = 0.101069, GooF = S = 1.04208, Restrained GooF = 1.04208 for all data
REM R1 = 0.038977 for 424 Fo > 4sig(Fo) and 0.052924 for all 529 data
REM 37 parameters refined using 0 restraints

END

WGHT      0.0352      0.0713

REM Highest difference peak  0.149,  deepest hole -0.166,  1-sigma level  0.034
Q1    1   0.3613  0.5934  0.4250  11.00000  0.05    0.15
Q2    1   0.5738  0.5730  0.3203  11.00000  0.05    0.14
;
_shelx_res_checksum              73439
