# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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-E
_database_code_depnum_ccdc_archive 'CCDC 2478415'
loop_
_audit_author_name
_audit_author_address
'Marko Rodic'
;University of Novi Sad
Serbia
;
_audit_update_record             
;
2025-08-05 deposited with the CCDC.	2025-11-04 downloaded from the CCDC.
;
#exp_code: data_HMPS_1903 

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; methyl (E)-2-(2-carbamoylhydrazineylidene)propanoate
;
_chemical_name_common            
; (E)-methyl pyruvate semicarbazone
;
_chemical_melting_point          471
_chemical_temperature_decomposition 471
_chemical_formula_moiety         'C5 H9 N3 O3'
_chemical_formula_sum            'C5 H9 N3 O3'
_chemical_formula_weight         159.15

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'
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'
H H 0.0000 0.0000 '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                   4.1764(4)
_cell_length_b                   7.4068(10)
_cell_length_c                   12.2230(13)
_cell_angle_alpha                90.144(10)
_cell_angle_beta                 97.506(9)
_cell_angle_gamma                91.316(10)
_cell_volume                     374.76(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    879
_cell_measurement_theta_min      9.4520
_cell_measurement_theta_max      70.9580

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: aqueous ethanol'
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    1.007
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89364
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 

Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  53.00   1.00    1.50    --   36.00 -57.00  30.00   84
  2  ω     44.00  75.00   1.00    1.50    --   36.00 -99.00 -60.00   31
  3  ω     58.00  87.00   1.00    1.50    --   36.00-178.00 -90.00   29
  4  ω     49.00 124.00   1.00    6.00    --  108.00 -77.00 -60.00   75
  5  ω     69.00  98.00   1.00    6.00    --  108.00 -45.00-150.00   29
  6  ω     90.00 154.00   1.00    6.00    --  108.00  30.00-150.00   64
  7  ω    132.00 159.00   1.00    6.00    --  108.00 111.00 -30.00   27
  8  ω    102.00 174.00   1.00    6.00    --  108.00 111.00  30.00   72
  9  ω    143.00 176.00   1.00    6.00    --  108.00  45.00 120.00   33
 10  ω    113.00 165.00   1.00    6.00    --  108.00  15.00 -30.00   52
 11  ω     91.00 136.00   1.00    6.00    --  108.00  45.00 120.00   45
 12  ω     61.00 126.00   1.00    6.00    --  108.00 -61.00  60.00   65
 13  ω     84.00 109.00   1.00    6.00    --  108.00 -94.00  90.00   25
 14  ω     70.00  97.00   1.00    6.00    --  108.00-111.00  90.00   27
 15  ω     42.00  69.00   1.00    6.00    --  108.00 -94.00  90.00   27
 16  ω     40.00 129.00   1.00    6.00    --  108.00 -30.00 -60.00   89
 17  ω     71.00 110.00   1.00    6.00    --  108.00  15.00 -30.00   39
 18  ω     65.00  92.00   1.00    1.50    --   36.00  77.00-120.00   27
 19  ω     61.00 101.00   1.00    1.50    --   36.00 178.00-150.00   40
 20  ω     66.00  97.00   1.00    6.00    --  108.00 178.00-150.00   31
 21  ω     73.00 146.00   1.00    6.00    --  108.00 178.00 -30.00   73
 22  ω     71.00  96.00   1.00    1.50    --   36.00 178.00 120.00   25
 23  ω     42.00 107.00   1.00    1.50    --   36.00  19.00  30.00   65
 24  ω     12.00  63.00   1.00    1.50    --   36.00  77.00-120.00   51
 25  ω    -31.00  26.00   1.00    1.50    --   36.00 -37.00 -90.00   57
;
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0075430000
_diffrn_orient_matrix_UB_12      0.0777153000
_diffrn_orient_matrix_UB_13      -0.1164509000
_diffrn_orient_matrix_UB_21      0.0761766000
_diffrn_orient_matrix_UB_22      -0.1881979000
_diffrn_orient_matrix_UB_23      -0.0424478000
_diffrn_orient_matrix_UB_31      -0.3642098000
_diffrn_orient_matrix_UB_32      -0.0427493000
_diffrn_orient_matrix_UB_33      -0.0282707000

_diffrn_reflns_number            2123
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.647
_diffrn_reflns_theta_max         71.139
_diffrn_reflns_theta_full        67.885
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1393
_reflns_number_gt                1238
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
; Mercury (Macrae et. al., 2020) and VESTA (Momma & Izumi, 2011)
;
_computing_publication_material  
; PLATON (Spek, 2009) and Huebschle et al., 2011
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+0.0225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1393
_refine_ls_number_parameters     114
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.086
_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 0.7351(3) 0.05967(15) 0.67867(9) 0.0693(4) Uani 1 1 d . . . . .
N1 N 0.2960(3) 0.40403(15) 0.77298(9) 0.0472(3) Uani 1 1 d . . . . .
C1 C 0.5924(3) 0.19733(17) 0.68385(11) 0.0477(4) Uani 1 1 d . . . . .
O2 O 0.5575(3) 0.31598(14) 0.60170(9) 0.0593(4) Uani 1 1 d . . . . .
N2 N 0.1524(3) 0.46361(16) 0.85888(10) 0.0514(3) Uani 1 1 d D . . . .
H2 H 0.159(4) 0.415(3) 0.9249(13) 0.062 Uiso 1 1 d D U . . .
C2 C 0.4406(3) 0.25281(17) 0.78214(11) 0.0463(4) Uani 1 1 d . . . . .
N3 N 0.0044(4) 0.71103(19) 0.75318(12) 0.0698(5) Uani 1 1 d . . . . .
H3A H 0.111(5) 0.665(3) 0.706(2) 0.075(6) Uiso 1 1 d . . . . .
H3B H -0.079(5) 0.812(3) 0.745(2) 0.078(6) Uiso 1 1 d . . . . .
O3 O -0.1247(3) 0.68789(16) 0.92588(9) 0.0677(4) Uani 1 1 d . . . . .
C3 C 0.0029(4) 0.62839(19) 0.84900(12) 0.0513(4) Uani 1 1 d . . . . .
C4 C 0.4691(4) 0.1299(2) 0.87960(12) 0.0575(4) Uani 1 1 d . . . . .
H4A H 0.573079 0.021218 0.862088 0.086 Uiso 1 1 calc R U . . .
H4B H 0.257615 0.100401 0.897989 0.086 Uiso 1 1 calc R U . . .
H4C H 0.594954 0.189088 0.941309 0.086 Uiso 1 1 calc R U . . .
C5 C 0.7035(5) 0.2713(2) 0.50526(14) 0.0676(5) Uani 1 1 d . . . . .
H5A H 0.611987 0.159181 0.474649 0.101 Uiso 1 1 calc R U . . .
H5B H 0.932098 0.259521 0.525191 0.101 Uiso 1 1 calc R U . . .
H5C H 0.663906 0.365173 0.451547 0.101 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
O1 C1 1.1983(17) . ?
N1 C2 1.2828(17) . ?
N1 N2 1.3532(17) . ?
C1 O2 1.3319(17) . ?
C1 C2 1.4910(19) . ?
O2 C5 1.4375(18) . ?
N2 C3 1.3820(17) . ?
N2 H2 0.882(15) . ?
C2 C4 1.4952(18) . ?
N3 C3 1.324(2) . ?
N3 H3A 0.85(2) . ?
N3 H3B 0.83(3) . ?
O3 C3 1.2251(19) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N2 118.62(11) . . ?
O1 C1 O2 122.63(13) . . ?
O1 C1 C2 123.60(12) . . ?
O2 C1 C2 113.77(11) . . ?
C1 O2 C5 116.33(11) . . ?
N1 N2 C3 118.16(11) . . ?
N1 N2 H2 127.4(13) . . ?
C3 N2 H2 114.1(13) . . ?
N1 C2 C1 115.15(12) . . ?
N1 C2 C4 126.79(13) . . ?
C1 C2 C4 118.06(11) . . ?
C3 N3 H3A 118.1(15) . . ?
C3 N3 H3B 118.2(17) . . ?
H3A N3 H3B 123(2) . . ?
O3 C3 N3 124.10(13) . . ?
O3 C3 N2 119.89(13) . . ?
N3 C3 N2 115.99(13) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

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 C1 O2 C5 -0.5(2) . . . . ?
C2 C1 O2 C5 179.03(14) . . . . ?
C2 N1 N2 C3 178.72(13) . . . . ?
N2 N1 C2 C1 -179.94(11) . . . . ?
N2 N1 C2 C4 0.3(2) . . . . ?
O1 C1 C2 N1 -179.59(14) . . . . ?
O2 C1 C2 N1 0.88(19) . . . . ?
O1 C1 C2 C4 0.2(2) . . . . ?
O2 C1 C2 C4 -179.34(13) . . . . ?
N1 N2 C3 O3 -178.76(14) . . . . ?
N1 N2 C3 N3 2.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O3 0.882(15) 1.999(15) 2.8780(17) 173.8(18) 2_567 yes
N3 H3B O1 0.83(3) 2.13(3) 2.9394(17) 164(2) 1_465 yes

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035


_chemical_properties_physical    Photo-sensitive
####################################################################### 
# 
# 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-Z
_database_code_depnum_ccdc_archive 'CCDC 2478416'
loop_
_audit_author_name
_audit_author_address
'Marko Rodic'
;University of Novi Sad
Serbia
;
_audit_update_record             
;
2025-08-05 deposited with the CCDC.	2025-11-04 downloaded from the CCDC.
;
#exp_code: data_iso-HMPS-EtOAc_2278_oF_a 

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; Methyl (Z)-2-(2-carbamoylhydrazineylidene)propanoate
;
_chemical_name_common            
; (Z)-methyl pyruvate semicarbazone
;

_chemical_melting_point          404
_chemical_temperature_decomposition 404
_chemical_formula_moiety         'C5 H9 N3 O3'
_chemical_formula_sum            'C5 H9 N3 O3'
_chemical_formula_weight         159.15

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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   36.4109(10)
_cell_length_b                   23.9057(9)
_cell_length_c                   7.0463(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6133.3(3)
_cell_formula_units_Z            32
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5435
_cell_measurement_theta_min      2.7910
_cell_measurement_theta_max      26.9800

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'

_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
 
 Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00   7.00   1.00   10.00    --  -16.67 -99.00  90.00   28
  2  ω    -11.00  22.00   1.00   10.00    --  -16.67 -99.00-180.00   33
  3  ω      2.00  67.00   1.00   10.00    --   17.53  57.00   0.00   65
  4  ω     43.00  75.00   1.00   10.00    --   17.53 178.00-150.00   32
  5  ω    -50.00  34.00   1.00   10.00    --   17.53 -57.00 -90.00   84
  6  ω    -45.00  37.00   1.00   10.00    --   17.53 -77.00-180.00   82
  7  ω      7.00  80.00   1.00   10.00    --   17.53  37.00  90.00   73
  8  φ     90.00 360.00   1.00    0.50   0.00   0.00   0.00    --   270
;

_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0057117000
_diffrn_orient_matrix_UB_12      -0.0237073000
_diffrn_orient_matrix_UB_13      0.0528051000
_diffrn_orient_matrix_UB_21      -0.0177002000
_diffrn_orient_matrix_UB_22      0.0119897000
_diffrn_orient_matrix_UB_23      0.0108868000
_diffrn_orient_matrix_UB_31      -0.0058119000
_diffrn_orient_matrix_UB_32      -0.0131878000
_diffrn_orient_matrix_UB_33      -0.0850159000

_diffrn_reflns_number            12757
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         29.252
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3654
_reflns_number_gt                2871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.830
_reflns_Friedel_fraction_full    0.988

_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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)+(0.0500P)²+0.1485P] 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_abs_structure_details 
; 
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3654
_refine_ls_number_parameters     223
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_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
O1A O 0.89465(5) 0.56924(7) 0.3354(3) 0.0769(6) Uani 1 1 d . . . . .
O2A O 0.94340(4) 0.62188(7) 0.2748(3) 0.0600(4) Uani 1 1 d . . . . .
O3A O 0.77738(4) 0.58892(7) 0.4487(3) 0.0764(6) Uani 1 1 d . . . . .
N1A N 0.85355(5) 0.67196(7) 0.3649(3) 0.0501(4) Uani 1 1 d . . . . .
N2A N 0.83310(5) 0.62590(9) 0.3972(3) 0.0563(5) Uani 1 1 d . . . . .
H2A H 0.8440(8) 0.5934(12) 0.394(4) 0.065(8) Uiso 1 1 d . . . . .
N3A N 0.78289(6) 0.68281(9) 0.4384(3) 0.0629(6) Uani 1 1 d . . . . .
H31A H 0.7601(9) 0.6878(12) 0.466(4) 0.075 Uiso 1 1 d . U . . .
H32A H 0.7974(8) 0.7106(13) 0.433(4) 0.075 Uiso 1 1 d . U . . .
C1A C 0.90810(6) 0.61457(9) 0.3129(3) 0.0485(5) Uani 1 1 d . . . . .
C2A C 0.88783(6) 0.66842(9) 0.3238(3) 0.0476(5) Uani 1 1 d . . . . .
C3A C 0.79593(6) 0.63138(10) 0.4300(3) 0.0540(5) Uani 1 1 d . . . . .
C4A C 0.90774(6) 0.72148(10) 0.2803(4) 0.0662(6) Uani 1 1 d . . . . .
H41A H 0.891310 0.752586 0.294983 0.099 Uiso 1 1 calc R U . . .
H42A H 0.916637 0.720357 0.152103 0.099 Uiso 1 1 calc R U . . .
H43A H 0.928082 0.725616 0.365836 0.099 Uiso 1 1 calc R U . . .
C5A C 0.96605(7) 0.57244(11) 0.2712(5) 0.0720(7) Uani 1 1 d . . . . .
H51A H 0.991466 0.583123 0.271536 0.108 Uiso 1 1 calc R U . . .
H52A H 0.960823 0.551253 0.158689 0.108 Uiso 1 1 calc R U . . .
H53A H 0.960949 0.550010 0.381130 0.108 Uiso 1 1 calc R U . . .
O1B O 0.58912(4) 0.71579(7) 0.6974(3) 0.0719(5) Uani 1 1 d . . . . .
O2B O 0.53930(4) 0.66236(7) 0.7060(3) 0.0734(5) Uani 1 1 d . . . . .
O3B O 0.70509(4) 0.69706(8) 0.5268(3) 0.0718(5) Uani 1 1 d . . . . .
N1B N 0.62851(5) 0.61409(8) 0.6043(3) 0.0518(5) Uani 1 1 d . . . . .
N2B N 0.64965(5) 0.66078(9) 0.5883(3) 0.0565(5) Uani 1 1 d . . . . .
H2B H 0.6403(8) 0.6964(12) 0.610(4) 0.067(7) Uiso 1 1 d . . . . .
N3B N 0.69758(7) 0.60309(10) 0.5076(4) 0.0707(6) Uani 1 1 d . . . . .
H31B H 0.7201(10) 0.5977(13) 0.479(4) 0.085 Uiso 1 1 d . U . . .
H32B H 0.6817(9) 0.5768(14) 0.517(5) 0.085 Uiso 1 1 d . U . . .
C1B C 0.57494(6) 0.67043(10) 0.6853(3) 0.0523(5) Uani 1 1 d . . . . .
C2B C 0.59445(6) 0.61693(9) 0.6476(3) 0.0496(5) Uani 1 1 d . . . . .
C3B C 0.68578(6) 0.65468(11) 0.5395(3) 0.0555(6) Uani 1 1 d . . . . .
C4B C 0.57415(7) 0.56254(9) 0.6615(4) 0.0634(6) Uani 1 1 d . . . . .
H41B H 0.590861 0.532152 0.639620 0.095 Uiso 1 1 calc R U . . .
H42B H 0.554992 0.561626 0.567888 0.095 Uiso 1 1 calc R U . . .
H43B H 0.563585 0.558991 0.785710 0.095 Uiso 1 1 calc R U . . .
C5B C 0.51726(7) 0.71182(14) 0.7407(7) 0.1071(14) Uani 1 1 d . . . . .
H51B H 0.491798 0.701552 0.746694 0.161 Uiso 1 1 calc R U . . .
H52B H 0.520892 0.738153 0.639565 0.161 Uiso 1 1 calc R U . . .
H53B H 0.524497 0.728520 0.858844 0.161 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
O1A C1A 1.200(3) . ?
O2A C1A 1.325(3) . ?
O2A C5A 1.442(3) . ?
O3A C3A 1.226(3) . ?
N1A C2A 1.284(3) . ?
N1A N2A 1.349(2) . ?
N2A C3A 1.379(3) . ?
N2A H2A 0.87(3) . ?
N3A C3A 1.319(3) . ?
N3A H31A 0.86(3) . ?
N3A H32A 0.85(3) . ?
C1A C2A 1.486(3) . ?
C2A C4A 1.493(3) . ?
C4A H41A 0.9600 . ?
C4A H42A 0.9600 . ?
C4A H43A 0.9600 . ?
C5A H51A 0.9600 . ?
C5A H52A 0.9600 . ?
C5A H53A 0.9600 . ?
O1B C1B 1.204(3) . ?
O2B C1B 1.320(3) . ?
O2B C5B 1.450(3) . ?
O3B C3B 1.236(3) . ?
N1B C2B 1.279(3) . ?
N1B N2B 1.361(3) . ?
N2B C3B 1.367(3) . ?
N2B H2B 0.93(3) . ?
N3B C3B 1.325(3) . ?
N3B H31B 0.85(4) . ?
N3B H32B 0.85(3) . ?
C1B C2B 1.487(3) . ?
C2B C4B 1.499(3) . ?
C4B H41B 0.9600 . ?
C4B H42B 0.9600 . ?
C4B H43B 0.9600 . ?
C5B H51B 0.9600 . ?
C5B H52B 0.9600 . ?
C5B H53B 0.9600 . ?

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
C1A O2A C5A 116.77(18) . . ?
C2A N1A N2A 121.40(19) . . ?
N1A N2A C3A 119.5(2) . . ?
N1A N2A H2A 118.2(19) . . ?
C3A N2A H2A 122.3(19) . . ?
C3A N3A H31A 119(2) . . ?
C3A N3A H32A 120(2) . . ?
H31A N3A H32A 120(3) . . ?
O1A C1A O2A 122.8(2) . . ?
O1A C1A C2A 124.95(19) . . ?
O2A C1A C2A 112.22(18) . . ?
N1A C2A C1A 123.48(19) . . ?
N1A C2A C4A 117.5(2) . . ?
C1A C2A C4A 118.96(18) . . ?
O3A C3A N3A 124.6(2) . . ?
O3A C3A N2A 118.7(2) . . ?
N3A C3A N2A 116.7(2) . . ?
C2A C4A H41A 109.5 . . ?
C2A C4A H42A 109.5 . . ?
H41A C4A H42A 109.5 . . ?
C2A C4A H43A 109.5 . . ?
H41A C4A H43A 109.5 . . ?
H42A C4A H43A 109.5 . . ?
O2A C5A H51A 109.5 . . ?
O2A C5A H52A 109.5 . . ?
H51A C5A H52A 109.5 . . ?
O2A C5A H53A 109.5 . . ?
H51A C5A H53A 109.5 . . ?
H52A C5A H53A 109.5 . . ?
C1B O2B C5B 116.3(2) . . ?
C2B N1B N2B 121.7(2) . . ?
N1B N2B C3B 118.5(2) . . ?
N1B N2B H2B 122.1(17) . . ?
C3B N2B H2B 119.4(17) . . ?
C3B N3B H31B 119(2) . . ?
C3B N3B H32B 117(2) . . ?
H31B N3B H32B 124(3) . . ?
O1B C1B O2B 123.0(2) . . ?
O1B C1B C2B 125.63(19) . . ?
O2B C1B C2B 111.33(19) . . ?
N1B C2B C1B 123.5(2) . . ?
N1B C2B C4B 116.6(2) . . ?
C1B C2B C4B 119.93(19) . . ?
O3B C3B N3B 124.5(2) . . ?
O3B C3B N2B 118.5(2) . . ?
N3B C3B N2B 117.0(2) . . ?
C2B C4B H41B 109.5 . . ?
C2B C4B H42B 109.5 . . ?
H41B C4B H42B 109.5 . . ?
C2B C4B H43B 109.5 . . ?
H41B C4B H43B 109.5 . . ?
H42B C4B H43B 109.5 . . ?
O2B C5B H51B 109.5 . . ?
O2B C5B H52B 109.5 . . ?
H51B C5B H52B 109.5 . . ?
O2B C5B H53B 109.5 . . ?
H51B C5B H53B 109.5 . . ?
H52B C5B H53B 109.5 . . ?

_refine_diff_density_max         0.113
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036

