# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_DPP-diEt
_audit_block_doi                 10.5517/ccdc.csd.cc28kjr4
_database_code_depnum_ccdc_archive 'CCDC 2102226'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/anie.202108978 2021
loop_
_audit_author_name
_audit_author_address
'Ranita Samanta'
;IISER Kolkata
India
;
_audit_update_record             
;
2021-08-11 deposited with the CCDC.	2022-12-16 downloaded from the CCDC.
;
_audit_creation_date             2021-08-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
2,5-diethyl-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
_chemical_formula_moiety         'C18 H16 N2 O2 S2'
_chemical_formula_sum            'C18 H16 N2 O2 S2'
_chemical_formula_weight         356.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
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'
S S 0.3331 0.5567 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.3077(2)
_cell_length_b                   10.6410(3)
_cell_length_c                   14.3047(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.421(3)
_cell_angle_gamma                90
_cell_volume                     801.15(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4475
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.7170
_cell_measurement_theta_min      3.0570
_shelx_estimated_absorpt_T_max   0.745
_shelx_estimated_absorpt_T_min   0.368
_exptl_absorpt_coefficient_mu    3.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6826
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        65.783
_diffrn_reflns_theta_max         65.783
_diffrn_reflns_theta_min         5.196
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     57.00 123.00   1.00    1.00    --   25.52 178.00 150.00   66
  2  ω     57.00 123.00   1.00    1.00    --   25.52 178.00 -90.00   66
  3  ω    -13.00 102.00   1.00    1.00    --   25.52  57.00-180.00  115
  4  ω      1.00  82.00   1.00    1.00    --   25.52 -99.00 -30.00   81
  5  ω     27.00 145.00   1.00    2.00    --   66.76  61.00  90.00  118
  6  ω     19.00 119.00   1.00    2.00    --   66.76-120.00 100.00  100
  7  ω    -14.00 116.00   1.00    2.00    --   66.76 -45.00-180.00  130
  8  ω     12.00 116.00   1.00    2.00    --   66.76-111.00  30.00  104
  9  ω    100.00 153.00   1.00    2.00    --   66.76 111.00-120.00   53
 10  ω    100.00 153.00   1.00    2.00    --   66.76 111.00 -60.00   53
 11  ω    100.00 153.00   1.00    2.00    --   66.76 111.00  90.00   53
 12  ω     28.00 146.00   1.00    8.00    --  108.00 -65.00 150.00  118
 13  ω     20.00 113.00   1.00    8.00    --  108.00-104.00  60.00   93
 14  ω    101.00 178.00   1.00    8.00    --  108.00 104.00-180.00   77
 15  ω     23.00 178.00   1.00    8.00    --  108.00  21.00 -60.00  155
 16  ω     30.00 148.00   1.00    8.00    --  108.00 -54.00 -30.00  118
 17  ω     27.00 160.00   1.00    8.00    --  108.00 -43.00 -30.00  133
 18  ω    101.00 178.00   1.00    8.00    --  108.00 104.00 120.00   77
 19  ω    101.00 178.00   1.00    8.00    --  108.00 104.00 -60.00   77
 20  ω     20.00 113.00   1.00    8.00    --  108.00-104.00-150.00   93
 21  ω    101.00 178.00   1.00    8.00    --  108.00 104.00 -30.00   77
 22  ω     17.00 178.00   1.00    8.00    --  108.00  11.00  90.00  161
 23  ω    -19.00 113.00   1.00    1.00    --   25.52  77.00-120.00  132
 24  ω    -13.00 102.00   1.00    1.00    --   25.52  57.00  60.00  115
 25  ω    -13.00 102.00   1.00    1.00    --   25.52  57.00   0.00  115
 26  ω     27.00 145.00   1.00    2.00    --   66.76  61.00-120.00  118
 27  ω     27.00 145.00   1.00    2.00    --   66.76  61.00 -60.00  118
 28  ω     27.00 145.00   1.00    2.00    --   66.76  61.00  30.00  118
 29  ω     26.00 150.00   1.00    2.00    --   66.76  70.00 -30.70  124
 30  ω     22.00 154.00   1.00    2.00    --   66.76  77.00 120.00  132
 31  ω     27.00 145.00   1.00    2.00    --   66.76  61.00-180.00  118
 32  ω     30.00 134.00   1.00    8.00    --  108.00 -54.00  90.00  104
 33  ω    101.00 178.00   1.00    8.00    --  108.00 104.00  90.00   77
 34  ω     33.00 178.00   1.00    8.00    --  108.00  32.00-180.00  145
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0682827000
_diffrn_orient_matrix_UB_12      0.0740212000
_diffrn_orient_matrix_UB_13      -0.0858175000
_diffrn_orient_matrix_UB_21      0.1988731000
_diffrn_orient_matrix_UB_22      0.0757368000
_diffrn_orient_matrix_UB_23      0.0649910000
_diffrn_orient_matrix_UB_31      0.2035867000
_diffrn_orient_matrix_UB_32      -0.0986684000
_diffrn_orient_matrix_UB_33      -0.0145900000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1309
_reflns_number_total             1391
_reflns_odcompleteness_completeness 97.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0773P)²+0.5579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1487
_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:
 C8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.04058(18) 0.70126(8) 0.25177(6) 0.0712(4) Uani 1 1 d . . . . .
O1 O 0.8410(4) 0.71722(18) 0.54414(15) 0.0579(6) Uani 1 1 d . . . . .
N1 N 0.4844(4) 0.6807(2) 0.43525(15) 0.0451(5) Uani 1 1 d . . . . .
C5 C 0.3153(4) 0.5829(2) 0.41014(16) 0.0416(6) Uani 1 1 d . . . . .
C6 C 0.3915(5) 0.4826(2) 0.46866(17) 0.0434(6) Uani 1 1 d . . . . .
C7 C 0.6724(4) 0.6456(3) 0.51084(18) 0.0444(6) Uani 1 1 d . . . . .
C3 C -0.0929(5) 0.4967(3) 0.32544(17) 0.0464(6) Uani 1 1 d . . . . .
H3 H -0.097020 0.425429 0.362875 0.056 Uiso 1 1 calc R U . . .
C4 C 0.1010(5) 0.5873(2) 0.33707(16) 0.0443(6) Uani 1 1 d . . . . .
C8 C 0.4816(5) 0.8083(3) 0.3982(2) 0.0525(7) Uani 1 1 d . . . . .
H8A H 0.443848 0.805128 0.330094 0.063 Uiso 1 1 calc R U . . .
H8B H 0.649480 0.844632 0.413503 0.063 Uiso 1 1 calc R U . . .
C2 C -0.2792(6) 0.5271(3) 0.2503(2) 0.0615(8) Uani 1 1 d . . . . .
H2 H -0.422742 0.477913 0.233432 0.074 Uiso 1 1 calc R U . . .
C9 C 0.2902(6) 0.8922(3) 0.4365(2) 0.0615(8) Uani 1 1 d . . . . .
H9A H 0.295263 0.974253 0.408934 0.092 Uiso 1 1 calc R U . . .
H9B H 0.330358 0.898601 0.503764 0.092 Uiso 1 1 calc R U . . .
H9C H 0.123276 0.857216 0.421333 0.092 Uiso 1 1 calc R U . . .
C1 C -0.2337(6) 0.6320(3) 0.2052(2) 0.0676(9) Uani 1 1 d . . . . .
H1 H -0.340288 0.663727 0.153900 0.081 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
S1 C4 1.721(3) . ?
S1 C1 1.690(4) . ?
O1 C7 1.224(3) . ?
N1 C5 1.391(3) . ?
N1 C7 1.423(3) . ?
N1 C8 1.457(3) . ?
C5 C6 1.384(3) . ?
C5 C4 1.443(3) . ?
C6 C6 1.415(5) 3_666 ?
C6 C7 1.444(4) 3_666 ?
C3 H3 0.9300 . ?
C3 C4 1.405(4) . ?
C3 C2 1.402(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.508(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.327(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 H1 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
C1 S1 C4 92.56(15) . . ?
C5 N1 C7 111.4(2) . . ?
C5 N1 C8 128.9(2) . . ?
C7 N1 C8 119.6(2) . . ?
N1 C5 C4 125.8(2) . . ?
C6 C5 N1 107.0(2) . . ?
C6 C5 C4 127.2(2) . . ?
C5 C6 C6 109.4(3) . 3_666 ?
C5 C6 C7 142.5(2) . 3_666 ?
C6 C6 C7 108.2(3) 3_666 3_666 ?
O1 C7 N1 122.5(2) . . ?
O1 C7 C6 133.5(2) . 3_666 ?
N1 C7 C6 104.0(2) . 3_666 ?
C4 C3 H3 124.3 . . ?
C2 C3 H3 124.3 . . ?
C2 C3 C4 111.5(3) . . ?
C5 C4 S1 126.5(2) . . ?
C3 C4 S1 109.47(18) . . ?
C3 C4 C5 124.1(2) . . ?
N1 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
N1 C8 C9 113.3(2) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C3 C2 H2 122.8 . . ?
C1 C2 C3 114.4(3) . . ?
C1 C2 H2 122.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S1 C1 H1 123.9 . . ?
C2 C1 S1 112.1(2) . . ?
C2 C1 H1 123.9 . . ?

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 C5 C6 C6 0.4(4) . . . 3_666 ?
N1 C5 C6 C7 179.9(3) . . . 3_666 ?
N1 C5 C4 S1 12.7(4) . . . . ?
N1 C5 C4 C3 -167.2(2) . . . . ?
C5 N1 C7 O1 179.8(3) . . . . ?
C5 N1 C7 C6 0.1(3) . . . 3_666 ?
C5 N1 C8 C9 77.6(3) . . . . ?
C6 C5 C4 S1 -167.7(2) . . . . ?
C6 C5 C4 C3 12.3(4) . . . . ?
C7 N1 C5 C6 -0.3(3) . . . . ?
C7 N1 C5 C4 179.3(2) . . . . ?
C7 N1 C8 C9 -98.9(3) . . . . ?
C3 C2 C1 S1 -0.2(4) . . . . ?
C4 S1 C1 C2 -0.6(3) . . . . ?
C4 C5 C6 C6 -179.2(3) . . . 3_666 ?
C4 C5 C6 C7 0.3(6) . . . 3_666 ?
C4 C3 C2 C1 1.1(4) . . . . ?
C8 N1 C5 C6 -177.0(3) . . . . ?
C8 N1 C5 C4 2.6(4) . . . . ?
C8 N1 C7 O1 -3.1(4) . . . . ?
C8 N1 C7 C6 177.1(2) . . . 3_666 ?
C2 C3 C4 S1 -1.5(3) . . . . ?
C2 C3 C4 C5 178.4(2) . . . . ?
C1 S1 C4 C5 -178.7(2) . . . . ?
C1 S1 C4 C3 1.2(2) . . . . ?

_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 2.007
_oxdiff_exptl_absorpt_empirical_full_min 0.459
