# Supplementary Information (SI) for Sustainable Energy & Fuels.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2325245'
loop_
_audit_author_name
_audit_author_address
'Ms. Rupansha'
;Indian Institute of Technology Madras, Chennai
India
;
_audit_update_record             
;
2024-01-13 deposited with the CCDC.	2025-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        5-nitro-2,3-dichloro-1,4-naphthoquinone
_chemical_name_common            5-DCNNQ
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H3 Cl2 N O4'
_chemical_formula_sum            'C10 H3 Cl2 N O4'
_chemical_formula_weight         272.03
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'
Cl Cl 0.1484 0.1585 '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                   9.1782(18)
_cell_length_b                   14.990(3)
_cell_length_c                   7.7606(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.925(6)
_cell_angle_gamma                90
_cell_volume                     1040.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4292
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      25.91

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.624
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4560
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17804
_diffrn_reflns_av_unetI/netI     0.1304
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             17804
_reflns_number_gt                10604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0795P)²+0.6400P] 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         17804
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2288
_refine_ls_wR_factor_gt          0.1899
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.1839(8) 0.5495(4) 0.2694(10) 0.0387(16) Uani 1 1 d . . . . .
C2 C 0.3506(7) 0.5544(4) 0.3084(9) 0.0346(15) Uani 1 1 d . . . . .
C3 C 0.4204(6) 0.6440(4) 0.3373(9) 0.0321(14) Uani 1 1 d . . . . .
C4 C 0.5754(7) 0.6503(5) 0.3765(10) 0.0433(17) Uani 1 1 d . . . . .
H4 H 0.634648 0.597956 0.382192 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6434(7) 0.7331(5) 0.4073(12) 0.0486(19) Uani 1 1 d . . . . .
H5 H 0.749286 0.737177 0.440037 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5585(7) 0.8093(5) 0.3907(11) 0.0456(18) Uani 1 1 d . . . . .
H6 H 0.605244 0.866087 0.409260 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4055(7) 0.8026(4) 0.3472(9) 0.0358(15) Uani 1 1 d . . . . .
C8 C 0.3325(6) 0.7207(4) 0.3254(9) 0.0329(14) Uani 1 1 d . . . . .
C9 C 0.1672(7) 0.7133(5) 0.3059(10) 0.0426(17) Uani 1 1 d . . . . .
C10 C 0.1002(7) 0.6229(5) 0.2657(10) 0.0396(16) Uani 1 1 d . . . . .
N1 N 0.3209(6) 0.8877(4) 0.3136(8) 0.0399(14) Uani 1 1 d . . . . .
O1 O 0.2522(6) 0.9013(3) 0.1653(7) 0.0536(14) Uani 1 1 d . . . . .
O2 O 0.3346(7) 0.9397(4) 0.4347(8) 0.0669(17) Uani 1 1 d . . . . .
O3 O 0.0923(6) 0.7752(4) 0.3326(10) 0.074(2) Uani 1 1 d . . . . .
O4 O 0.4253(5) 0.4873(3) 0.3121(7) 0.0480(13) Uani 1 1 d . . . . .
Cl1 Cl 0.1084(2) 0.44529(13) 0.2387(3) 0.0633(7) Uani 1 1 d . . . . .
Cl2 Cl -0.0897(2) 0.61811(16) 0.2282(4) 0.0701(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.338(9) . ?
C1 C2 1.494(9) . ?
C1 Cl1 1.704(7) . ?
C2 O4 1.214(8) . ?
C2 C3 1.482(9) . ?
C3 C4 1.390(9) . ?
C3 C8 1.396(8) . ?
C4 C5 1.386(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(9) . ?
C7 N1 1.486(8) . ?
C8 C9 1.494(9) . ?
C9 O3 1.201(8) . ?
C9 C10 1.491(9) . ?
C10 Cl2 1.703(6) . ?
N1 O1 1.200(7) . ?
N1 O2 1.206(8) . ?

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
C10 C1 C2 121.4(6) . . ?
C10 C1 Cl1 122.5(5) . . ?
C2 C1 Cl1 116.1(5) . . ?
O4 C2 C3 121.6(6) . . ?
O4 C2 C1 120.7(6) . . ?
C3 C2 C1 117.6(5) . . ?
C4 C3 C8 120.4(6) . . ?
C4 C3 C2 118.8(6) . . ?
C8 C3 C2 120.8(5) . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.3(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.4(6) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C8 122.2(6) . . ?
C6 C7 N1 116.5(6) . . ?
C8 C7 N1 121.2(6) . . ?
C7 C8 C3 117.6(5) . . ?
C7 C8 C9 121.9(6) . . ?
C3 C8 C9 120.3(6) . . ?
O3 C9 C10 120.9(6) . . ?
O3 C9 C8 122.1(6) . . ?
C10 C9 C8 116.8(6) . . ?
C1 C10 C9 122.3(6) . . ?
C1 C10 Cl2 122.0(5) . . ?
C9 C10 Cl2 115.6(5) . . ?
O1 N1 O2 125.3(6) . . ?
O1 N1 C7 117.1(6) . . ?
O2 N1 C7 117.4(6) . . ?

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
C10 C1 C2 O4 179.7(7) . . . . ?
Cl1 C1 C2 O4 2.0(9) . . . . ?
C10 C1 C2 C3 -1.9(10) . . . . ?
Cl1 C1 C2 C3 -179.5(5) . . . . ?
O4 C2 C3 C4 -2.6(10) . . . . ?
C1 C2 C3 C4 179.0(6) . . . . ?
O4 C2 C3 C8 177.4(6) . . . . ?
C1 C2 C3 C8 -1.0(9) . . . . ?
C8 C3 C4 C5 1.2(11) . . . . ?
C2 C3 C4 C5 -178.8(7) . . . . ?
C3 C4 C5 C6 -3.2(13) . . . . ?
C4 C5 C6 C7 1.4(12) . . . . ?
C5 C6 C7 C8 2.5(11) . . . . ?
C5 C6 C7 N1 -174.0(7) . . . . ?
C6 C7 C8 C3 -4.4(10) . . . . ?
N1 C7 C8 C3 171.9(6) . . . . ?
C6 C7 C8 C9 170.3(7) . . . . ?
N1 C7 C8 C9 -13.3(10) . . . . ?
C4 C3 C8 C7 2.5(10) . . . . ?
C2 C3 C8 C7 -177.5(6) . . . . ?
C4 C3 C8 C9 -172.3(7) . . . . ?
C2 C3 C8 C9 7.7(10) . . . . ?
C7 C8 C9 O3 -10.7(12) . . . . ?
C3 C8 C9 O3 163.8(7) . . . . ?
C7 C8 C9 C10 174.2(7) . . . . ?
C3 C8 C9 C10 -11.3(10) . . . . ?
C2 C1 C10 C9 -2.1(11) . . . . ?
Cl1 C1 C10 C9 175.4(6) . . . . ?
C2 C1 C10 Cl2 -178.0(5) . . . . ?
Cl1 C1 C10 Cl2 -0.5(10) . . . . ?
O3 C9 C10 C1 -166.6(8) . . . . ?
C8 C9 C10 C1 8.5(11) . . . . ?
O3 C9 C10 Cl2 9.5(10) . . . . ?
C8 C9 C10 Cl2 -175.4(5) . . . . ?
C6 C7 N1 O1 112.9(8) . . . . ?
C8 C7 N1 O1 -63.7(8) . . . . ?
C6 C7 N1 O2 -62.5(9) . . . . ?
C8 C7 N1 O2 121.0(7) . . . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.073



