# Supplementary Information (SI) for ChemComm.
# 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_z124_0727_auto
_database_code_depnum_ccdc_archive 'CCDC 2364728'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2024-06-23 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl 2-(1,2-diphenylhydrazineyl)-2-oxoacetate'
_chemical_formula_moiety         'C16 H16 N2 O3'
_chemical_formula_sum            'C16 H16 N2 O3'
_chemical_formula_weight         284.31
_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 0.0181 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'

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

_cell_length_a                   8.42770(10)
_cell_length_b                   11.4571(2)
_cell_length_c                   31.6448(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3055.53(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5988
_cell_measurement_temperature    304.62(10)
_cell_measurement_theta_max      76.1220
_cell_measurement_theta_min      2.7810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            11023
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.915
_diffrn_reflns_theta_min         2.793
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      304.62(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -34.00   0.50    0.10    --  -46.61 -19.00  33.00  162
  2  ω   -132.00 -82.00   0.50    0.30    -- -102.00 -77.00 120.00  100
  3  ω   -170.00-135.00   0.50    0.30    -- -102.00 -77.00 120.00   70
  4  ω    -68.00 -43.00   0.50    0.30    -- -102.00  61.00-180.00   50
  5  ω   -106.00 -31.00   0.50    0.30    -- -102.00 105.00  -8.00  150
  6  ω    -15.00  29.00   0.50    0.10    --   46.61 -19.00-120.00   88
  7  ω     40.00  90.00   0.50    0.30    --  104.21 -94.00 -90.00  100
  8  ω     39.00  87.00   0.50    0.10    --   46.61-125.00-150.00   96
  9  ω     97.00 156.00   0.50    0.30    --  104.21  19.00-158.00  118
 10  ω     38.00  63.00   0.50    0.30    --  104.21 -61.00 -60.00   50
 11  ω     38.00 101.00   0.50    0.30    --  104.21-132.00 176.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0917763000
_diffrn_orient_matrix_UB_12      0.0156041000
_diffrn_orient_matrix_UB_13      -0.0417187000
_diffrn_orient_matrix_UB_21      -0.1509936000
_diffrn_orient_matrix_UB_22      -0.0306329000
_diffrn_orient_matrix_UB_23      -0.0250744000
_diffrn_orient_matrix_UB_31      -0.0466041000
_diffrn_orient_matrix_UB_32      0.1300388000
_diffrn_orient_matrix_UB_33      -0.0009081000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2530
_reflns_number_total             3055
_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       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²+0.3732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1164
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 0.24101(14) 0.16628(8) 0.60587(3) 0.0637(3) Uani 1 1 d . . . . .
O2 O 0.40958(13) 0.23639(10) 0.69102(3) 0.0691(3) Uani 1 1 d . . . . .
O3 O 0.15892(12) 0.29956(11) 0.68380(3) 0.0673(3) Uani 1 1 d . . . . .
N1 N 0.35462(12) 0.34542(8) 0.60102(3) 0.0419(2) Uani 1 1 d . . . . .
N2 N 0.40509(12) 0.43959(8) 0.62618(3) 0.0430(2) Uani 1 1 d . . . . .
H2 H 0.3477(18) 0.5037(14) 0.6219(5) 0.056(4) Uiso 1 1 d . . . . .
C1 C 0.29430(14) 0.25432(10) 0.62220(4) 0.0424(3) Uani 1 1 d . . . . .
C2 C 0.77968(19) 0.58397(13) 0.65328(5) 0.0644(4) Uani 1 1 d . . . . .
H2A H 0.812493 0.653095 0.665964 0.077 Uiso 1 1 calc R U . . .
C3 C 0.2959(3) 0.45044(16) 0.49162(5) 0.0831(6) Uani 1 1 d . . . . .
H3 H 0.251717 0.514174 0.477728 0.100 Uiso 1 1 calc R U . . .
C4 C 0.57012(15) 0.45940(9) 0.62875(4) 0.0419(3) Uani 1 1 d . . . . .
C5 C 0.84189(19) 0.40122(15) 0.62198(6) 0.0705(4) Uani 1 1 d . . . . .
H5 H 0.916800 0.346583 0.613356 0.085 Uiso 1 1 calc R U . . .
C6 C 0.29850(15) 0.26518(11) 0.67015(4) 0.0454(3) Uani 1 1 d . . . . .
C7 C 0.1379(3) 0.3086(2) 0.72952(6) 0.1006(7) Uani 1 1 d . . . . .
H7A H 0.028827 0.290571 0.736805 0.121 Uiso 1 1 calc R U . . .
H7B H 0.206007 0.252385 0.743563 0.121 Uiso 1 1 calc R U . . .
C8 C 0.35898(15) 0.35140(10) 0.55549(4) 0.0458(3) Uani 1 1 d . . . . .
C9 C 0.89107(19) 0.50363(15) 0.64049(6) 0.0719(5) Uani 1 1 d . . . . .
H9 H 0.998617 0.518440 0.644312 0.086 Uiso 1 1 calc R U . . .
C10 C 0.62006(17) 0.56326(11) 0.64753(4) 0.0523(3) Uani 1 1 d . . . . .
H10 H 0.545811 0.618394 0.656150 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4323(3) 0.26986(17) 0.48904(5) 0.0812(5) Uani 1 1 d . . . . .
H11 H 0.480016 0.210831 0.473376 0.097 Uiso 1 1 calc R U . . .
C12 C 0.68191(17) 0.37857(12) 0.61605(5) 0.0546(3) Uani 1 1 d . . . . .
H12 H 0.649881 0.309015 0.603535 0.066 Uiso 1 1 calc R U . . .
C13 C 0.3637(3) 0.36298(18) 0.46875(5) 0.0845(6) Uani 1 1 d . . . . .
H13 H 0.363608 0.366341 0.439387 0.101 Uiso 1 1 calc R U . . .
C14 C 0.4307(2) 0.26345(14) 0.53267(5) 0.0617(4) Uani 1 1 d . . . . .
H14 H 0.477427 0.200560 0.546462 0.074 Uiso 1 1 calc R U . . .
C15 C 0.1766(4) 0.4251(3) 0.74388(8) 0.1339(11) Uani 1 1 d . . . . .
H15A H 0.104686 0.480112 0.731352 0.201 Uiso 1 1 calc R U . . .
H15B H 0.283324 0.443915 0.735714 0.201 Uiso 1 1 calc R U . . .
H15C H 0.167548 0.428657 0.774093 0.201 Uiso 1 1 calc R U . . .
C16 C 0.2920(2) 0.44549(13) 0.53530(5) 0.0642(4) Uani 1 1 d . . . . .
H16 H 0.244725 0.505057 0.550795 0.077 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 1.2191(15) . ?
O2 C6 1.1922(16) . ?
O3 C6 1.3136(16) . ?
O3 C7 1.461(2) . ?
N1 N2 1.4066(13) . ?
N1 C1 1.3406(15) . ?
N1 C8 1.4429(15) . ?
N2 C4 1.4116(16) . ?
C1 C6 1.5227(17) . ?
C2 C9 1.376(2) . ?
C2 C10 1.378(2) . ?
C3 C13 1.362(3) . ?
C3 C16 1.384(2) . ?
C4 C10 1.3951(17) . ?
C4 C12 1.3809(19) . ?
C5 C9 1.375(2) . ?
C5 C12 1.386(2) . ?
C7 C15 1.448(4) . ?
C8 C14 1.379(2) . ?
C8 C16 1.374(2) . ?
C11 C13 1.373(3) . ?
C11 C14 1.382(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
C6 O3 C7 117.09(13) . . ?
N2 N1 C8 121.40(9) . . ?
C1 N1 N2 115.40(10) . . ?
C1 N1 C8 123.09(9) . . ?
N1 N2 C4 117.00(10) . . ?
O1 C1 N1 124.89(11) . . ?
O1 C1 C6 119.90(10) . . ?
N1 C1 C6 115.20(10) . . ?
C9 C2 C10 120.81(13) . . ?
C13 C3 C16 120.70(17) . . ?
C10 C4 N2 117.32(11) . . ?
C12 C4 N2 123.21(11) . . ?
C12 C4 C10 119.35(12) . . ?
C9 C5 C12 120.70(15) . . ?
O2 C6 O3 127.15(12) . . ?
O2 C6 C1 123.21(11) . . ?
O3 C6 C1 109.36(10) . . ?
C15 C7 O3 110.4(2) . . ?
C14 C8 N1 119.96(12) . . ?
C16 C8 N1 119.40(12) . . ?
C16 C8 C14 120.63(13) . . ?
C5 C9 C2 119.37(14) . . ?
C2 C10 C4 119.84(13) . . ?
C13 C11 C14 120.28(17) . . ?
C4 C12 C5 119.93(13) . . ?
C3 C13 C11 120.00(15) . . ?
C8 C14 C11 119.23(15) . . ?
C8 C16 C3 119.13(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.181
_oxdiff_exptl_absorpt_empirical_full_min 0.800
