# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1944642'
loop_
_audit_author_name
_audit_author_address
'Zhiming Duan'
;Shanghai University
China
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,5-diethyl-3,6-bis(4-fluorothiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
_chemical_name_common            'difluorinated dithienyl-DPP'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 F2 N2 O2 S2'
_chemical_formula_weight         392.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 '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 0.0050 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0090 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0150 0.0090 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1080 0.1050 '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                   4.5260(9)
_cell_length_b                   18.489(4)
_cell_length_c                   19.838(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.22(3)
_cell_angle_gamma                90
_cell_volume                     1646.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30125
_cell_measurement_theta_min      1.39
_cell_measurement_theta_max      26.5

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.65251
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4388
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.387
_diffrn_reflns_theta_max         26.519
_diffrn_reflns_theta_full        23.048
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4388
_reflns_number_gt                4115
_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       blueice
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0725P)²+0.7889P] 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         4388
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
S1 S 1.12342(7) 0.46067(2) 0.69748(2) 0.02232(10) Uani 1 1 d . . . . .
F1 F 0.8685(2) 0.26448(5) 0.70788(5) 0.0317(2) Uani 1 1 d . . . . .
O1 O 0.7274(2) 0.64861(5) 0.48654(5) 0.01969(19) Uani 1 1 d . . . . .
N1 N 0.8472(2) 0.55470(5) 0.56273(5) 0.0164(2) Uani 1 1 d . . . . .
C1 C 1.1146(3) 0.37641(7) 0.73236(7) 0.0236(3) Uani 1 1 d . . . . .
H1 H 1.2282 0.3615 0.7735 0.028 Uiso 1 1 calc R U . . .
C2 C 0.9200(3) 0.33383(7) 0.69222(7) 0.0225(3) Uani 1 1 d . . . . .
C3 C 0.7742(3) 0.36666(7) 0.63361(6) 0.0211(2) Uani 1 1 d . . . . .
H3 H 0.6316 0.3433 0.6016 0.025 Uiso 1 1 calc R U . . .
C4 C 0.8657(3) 0.43747(6) 0.62861(6) 0.0171(2) Uani 1 1 d . . . . .
C5 C 0.7515(3) 0.48475(6) 0.57387(6) 0.0156(2) Uani 1 1 d . . . . .
C6 C 0.5236(3) 0.46966(6) 0.52176(6) 0.0165(2) Uani 1 1 d . . . . .
C7 C 0.6823(3) 0.58632(6) 0.50434(6) 0.0162(2) Uani 1 1 d . . . . .
C8 C 1.0753(3) 0.59779(7) 0.60315(6) 0.0192(2) Uani 1 1 d . . . . .
H8A H 1.1614 0.6326 0.5731 0.023 Uiso 1 1 calc R U . . .
H8B H 1.2373 0.5655 0.6232 0.023 Uiso 1 1 calc R U . . .
C9 C 0.9514(3) 0.63899(7) 0.65973(7) 0.0259(3) Uani 1 1 d . . . . .
H9A H 0.8638 0.6048 0.6893 0.039 Uiso 1 1 calc R U . . .
H9B H 0.7980 0.6729 0.6400 0.039 Uiso 1 1 calc R U . . .
H9C H 1.1125 0.6658 0.6864 0.039 Uiso 1 1 calc R U . . .
S2 S -0.13014(7) 0.18555(2) 0.53662(2) 0.02041(10) Uani 1 1 d . . . . .
F2 F -0.39207(19) 0.20748(5) 0.34694(4) 0.02638(19) Uani 1 1 d . . . . .
O2 O 0.6308(2) -0.03175(5) 0.64687(5) 0.01991(19) Uani 1 1 d . . . . .
N2 N 0.3196(2) 0.04949(6) 0.58295(5) 0.0164(2) Uani 1 1 d . . . . .
C10 C -0.3293(3) 0.22308(7) 0.46668(7) 0.0224(3) Uani 1 1 d . . . . .
H10 H -0.4655 0.2621 0.4674 0.027 Uiso 1 1 calc R U . . .
C11 C -0.2639(3) 0.18889(7) 0.40983(7) 0.0200(2) Uani 1 1 d . . . . .
C12 C -0.0560(3) 0.13256(7) 0.42015(6) 0.0188(2) Uani 1 1 d . . . . .
H12 H 0.0114 0.1047 0.3849 0.023 Uiso 1 1 calc R U . . .
C13 C 0.0379(3) 0.12301(6) 0.48866(6) 0.0169(2) Uani 1 1 d . . . . .
C14 C 0.2471(3) 0.06814(6) 0.51499(6) 0.0161(2) Uani 1 1 d . . . . .
C15 C 0.4105(3) 0.02330(6) 0.47762(6) 0.0164(2) Uani 1 1 d . . . . .
C16 C 0.2073(3) 0.07954(7) 0.64311(6) 0.0192(2) Uani 1 1 d . . . . .
H16A H 0.2075 0.0412 0.6779 0.023 Uiso 1 1 calc R U . . .
H16B H -0.0012 0.0955 0.6306 0.023 Uiso 1 1 calc R U . . .
C17 C 0.3915(3) 0.14310(8) 0.67334(7) 0.0249(3) Uani 1 1 d . . . . .
H17A H 0.5953 0.1269 0.6884 0.037 Uiso 1 1 calc R U . . .
H17B H 0.3029 0.1624 0.7122 0.037 Uiso 1 1 calc R U . . .
H17C H 0.3951 0.1810 0.6389 0.037 Uiso 1 1 calc R U . . .
C18 C 0.5334(3) -0.00727(6) 0.59098(6) 0.0164(2) 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
S1 C1 1.7071(14) . ?
S1 C4 1.7352(14) . ?
F1 C2 1.3464(15) . ?
O1 C7 1.2292(15) . ?
N1 C5 1.3903(15) . ?
N1 C7 1.4224(15) . ?
N1 C8 1.4612(15) . ?
C1 C2 1.3614(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.4009(17) . ?
C3 C4 1.3805(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.4386(16) . ?
C5 C6 1.3938(17) . ?
C6 C6 1.415(2) 3_666 ?
C6 C7 1.4445(16) 3_666 ?
C7 C6 1.4446(16) 3_666 ?
C8 C9 1.5208(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
S2 C10 1.7043(14) . ?
S2 C13 1.7328(13) . ?
F2 C11 1.3526(15) . ?
O2 C18 1.2271(15) . ?
N2 C14 1.3905(15) . ?
N2 C18 1.4226(16) . ?
N2 C16 1.4642(16) . ?
C10 C11 1.3574(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.4015(17) . ?
C12 C13 1.3834(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.4401(16) . ?
C14 C15 1.3861(17) . ?
C15 C15 1.417(2) 3_656 ?
C15 C18 1.4463(17) 3_656 ?
C16 C17 1.5200(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C15 1.4463(17) 3_656 ?

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 92.63(6) . . ?
C5 N1 C7 111.70(10) . . ?
C5 N1 C8 129.24(10) . . ?
C7 N1 C8 119.01(10) . . ?
C2 C1 S1 109.70(10) . . ?
C2 C1 H1 125.2 . . ?
S1 C1 H1 125.2 . . ?
F1 C2 C1 122.26(12) . . ?
F1 C2 C3 121.80(12) . . ?
C1 C2 C3 115.94(12) . . ?
C4 C3 C2 110.88(12) . . ?
C4 C3 H3 124.6 . . ?
C2 C3 H3 124.6 . . ?
C3 C4 C5 123.23(11) . . ?
C3 C4 S1 110.84(9) . . ?
C5 C4 S1 125.90(9) . . ?
N1 C5 C6 106.54(10) . . ?
N1 C5 C4 126.56(11) . . ?
C6 C5 C4 126.91(11) . . ?
C5 C6 C6 109.55(13) . 3_666 ?
C5 C6 C7 142.50(11) . 3_666 ?
C6 C6 C7 107.95(13) 3_666 3_666 ?
O1 C7 N1 122.01(11) . . ?
O1 C7 C6 133.73(11) . 3_666 ?
N1 C7 C6 104.25(10) . 3_666 ?
N1 C8 C9 112.18(11) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 S2 C13 92.77(6) . . ?
C14 N2 C18 111.47(10) . . ?
C14 N2 C16 129.21(10) . . ?
C18 N2 C16 119.32(10) . . ?
C11 C10 S2 109.80(10) . . ?
C11 C10 H10 125.1 . . ?
S2 C10 H10 125.1 . . ?
F2 C11 C10 122.36(12) . . ?
F2 C11 C12 121.72(12) . . ?
C10 C11 C12 115.92(12) . . ?
C13 C12 C11 110.86(12) . . ?
C13 C12 H12 124.6 . . ?
C11 C12 H12 124.6 . . ?
C12 C13 C14 123.57(11) . . ?
C12 C13 S2 110.64(9) . . ?
C14 C13 S2 125.78(9) . . ?
C15 C14 N2 107.05(10) . . ?
C15 C14 C13 126.72(11) . . ?
N2 C14 C13 126.22(11) . . ?
C14 C15 C15 109.29(13) . 3_656 ?
C14 C15 C18 142.60(11) . 3_656 ?
C15 C15 C18 108.10(13) 3_656 3_656 ?
N2 C16 C17 112.68(10) . . ?
N2 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N2 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 N2 122.37(11) . . ?
O2 C18 C15 133.55(12) . 3_656 ?
N2 C18 C15 104.08(10) . 3_656 ?

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.070



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: tetrahydrofuran'
_exptl_crystal_preparation       Luminescent
