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#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/73/7237339.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7237339
loop_
_publ_author_name
'Genevaz, Nicolas'
'Chávez, Patricia'
'Untilova, Viktoriia'
'Boeglin, Alex'
'Bailly, Corinne'
'Karmazin, Lydia'
'Biniek, Laure'
_publ_section_title
;
 Tuning crystallochromism in
 diketopyrrolopyrrole-co-thieno[3,2-b]thiophene derivatives by the
 architecture of their alkyl side chains
;
_journal_issue                   34
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9140
_journal_paper_doi               10.1039/C8TC02022A
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C30 H32 N2 O2 S4'
_chemical_formula_sum            'C30 H32 N2 O2 S4'
_chemical_formula_weight         580.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-04-26 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                106.954(5)
_cell_angle_beta                 94.112(4)
_cell_angle_gamma                97.995(5)
_cell_formula_units_Z            1
_cell_length_a                   4.8832(3)
_cell_length_b                   10.2613(6)
_cell_length_c                   14.1880(9)
_cell_measurement_reflns_used    1798
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.55
_cell_measurement_theta_min      4.57
_cell_volume                     668.68(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8272
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.896
_diffrn_reflns_theta_min         3.279
_diffrn_source                   'Cu-ImuS microfocus tube'
_exptl_absorpt_coefficient_mu    3.522
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       plate
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0533
_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)+(0.0662P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1616
_reflns_number_total             2326
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8tc02022a2.cif
_cod_data_source_block           cgng160906
_cod_database_code               7237339
_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.
;
_shelx_estimated_absorpt_t_min   0.485
_shelx_estimated_absorpt_t_max   0.816
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.5263(6) 0.6215(4) 0.9308(2) 0.0274(7) Uani 1 1 d . .
C2 C 0.5606(6) 0.4397(3) 0.9941(2) 0.0263(7) Uani 1 1 d . .
C3 C 0.7198(6) 0.4228(3) 0.9158(2) 0.0262(7) Uani 1 1 d . .
C4 C 0.8760(6) 0.3128(3) 0.8796(2) 0.0276(8) Uani 1 1 d . .
C5 C 0.9035(6) 0.2136(4) 0.9259(2) 0.0300(8) Uani 1 1 d . .
H5 H 0.8231 0.2111 0.9845 0.036 Uiso 1 1 calc R U
C6 C 1.0632(7) 0.1169(4) 0.8770(2) 0.0303(8) Uani 1 1 d . .
C7 C 1.1597(7) 0.1399(4) 0.7919(2) 0.0302(8) Uani 1 1 d . .
C8 C 1.3243(7) 0.0424(4) 0.7444(3) 0.0371(9) Uani 1 1 d . .
H8 H 1.4056 0.0423 0.6856 0.045 Uiso 1 1 calc R U
C9 C 1.3505(7) -0.0503(4) 0.7940(3) 0.0386(9) Uani 1 1 d . .
H9 H 1.4539 -0.1234 0.7730 0.046 Uiso 1 1 calc R U
C10 C 0.8351(7) 0.5679(4) 0.7980(2) 0.0303(8) Uani 1 1 d . .
H10A H 1.0194 0.5380 0.7955 0.036 Uiso 1 1 calc R U
H10B H 0.8661 0.6695 0.8121 0.036 Uiso 1 1 calc R U
C11 C 0.6636(7) 0.5011(4) 0.6968(2) 0.0333(8) Uani 1 1 d . .
H11A H 0.4720 0.5219 0.7009 0.040 Uiso 1 1 calc R U
H11B H 0.6519 0.3995 0.6786 0.040 Uiso 1 1 calc R U
C12 C 0.7899(7) 0.5526(4) 0.6162(3) 0.0357(8) Uani 1 1 d . .
H12A H 0.9944 0.5576 0.6255 0.043 Uiso 1 1 calc R U
H12B H 0.7184 0.4845 0.5507 0.043 Uiso 1 1 calc R U
C13 C 0.7270(7) 0.6933(4) 0.6155(3) 0.0357(8) Uani 1 1 d . .
H13A H 0.8113 0.7627 0.6790 0.043 Uiso 1 1 calc R U
H13B H 0.5229 0.6903 0.6114 0.043 Uiso 1 1 calc R U
C14 C 0.8345(7) 0.7397(4) 0.5303(3) 0.0390(9) Uani 1 1 d . .
H14A H 1.0406 0.7590 0.5409 0.047 Uiso 1 1 calc R U
H14B H 0.7777 0.6633 0.4676 0.047 Uiso 1 1 calc R U
C15 C 0.7283(8) 0.8670(4) 0.5198(3) 0.0521(11) Uani 1 1 d . .
H15A H 0.5243 0.8488 0.5094 0.078 Uiso 1 1 calc R U
H15B H 0.8002 0.8902 0.4629 0.078 Uiso 1 1 calc R U
H15C H 0.7917 0.9445 0.5803 0.078 Uiso 1 1 calc R U
N1 N 0.7034(5) 0.5332(3) 0.87882(19) 0.0276(6) Uani 1 1 d . .
O1 O 0.4755(5) 0.7222(2) 0.90704(16) 0.0322(6) Uani 1 1 d . .
S1 S 1.04843(18) 0.28319(10) 0.77241(6) 0.0342(3) Uani 1 1 d . .
S2 S 1.18045(19) -0.02426(9) 0.89796(7) 0.0389(3) Uani 1 1 d . .
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'
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
O1 C1 N1 121.6(3) . .
O1 C1 C2 134.2(3) . 2_667
N1 C1 C2 104.1(3) . 2_667
C3 C2 C2 109.5(4) . 2_667
C3 C2 C1 142.5(3) . 2_667
C2 C2 C1 107.9(4) 2_667 2_667
C2 C3 N1 107.0(3) . .
C2 C3 C4 126.9(3) . .
N1 C3 C4 126.1(3) . .
C5 C4 C3 122.7(3) . .
C5 C4 S1 111.0(2) . .
C3 C4 S1 126.3(3) . .
C4 C5 C6 112.5(3) . .
C4 C5 H5 123.7 . .
C6 C5 H5 123.7 . .
C7 C6 C5 114.1(3) . .
C7 C6 S2 110.6(3) . .
C5 C6 S2 135.3(3) . .
C6 C7 C8 113.2(3) . .
C6 C7 S1 110.6(3) . .
C8 C7 S1 136.2(3) . .
C9 C8 C7 111.1(3) . .
C9 C8 H8 124.4 . .
C7 C8 H8 124.4 . .
C8 C9 S2 114.0(3) . .
C8 C9 H9 123.0 . .
S2 C9 H9 123.0 . .
N1 C10 C11 113.3(3) . .
N1 C10 H10A 108.9 . .
C11 C10 H10A 108.9 . .
N1 C10 H10B 108.9 . .
C11 C10 H10B 108.9 . .
H10A C10 H10B 107.7 . .
C10 C11 C12 112.0(3) . .
C10 C11 H11A 109.2 . .
C12 C11 H11A 109.2 . .
C10 C11 H11B 109.2 . .
C12 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
C13 C12 C11 113.9(3) . .
C13 C12 H12A 108.8 . .
C11 C12 H12A 108.8 . .
C13 C12 H12B 108.8 . .
C11 C12 H12B 108.8 . .
H12A C12 H12B 107.7 . .
C12 C13 C14 113.8(3) . .
C12 C13 H13A 108.8 . .
C14 C13 H13A 108.8 . .
C12 C13 H13B 108.8 . .
C14 C13 H13B 108.8 . .
H13A C13 H13B 107.7 . .
C15 C14 C13 113.3(3) . .
C15 C14 H14A 108.9 . .
C13 C14 H14A 108.9 . .
C15 C14 H14B 108.9 . .
C13 C14 H14B 108.9 . .
H14A C14 H14B 107.7 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C3 N1 C1 111.4(3) . .
C3 N1 C10 130.0(3) . .
C1 N1 C10 118.6(3) . .
C7 S1 C4 91.79(16) . .
C9 S2 C6 91.05(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.227(4) .
C1 N1 1.425(4) .
C1 C2 1.446(5) 2_667
C2 C3 1.385(5) .
C2 C2 1.417(6) 2_667
C2 C1 1.446(5) 2_667
C3 N1 1.390(4) .
C3 C4 1.441(5) .
C4 C5 1.379(5) .
C4 S1 1.760(3) .
C5 C6 1.403(5) .
C5 H5 0.9500 .
C6 C7 1.397(5) .
C6 S2 1.724(3) .
C7 C8 1.417(5) .
C7 S1 1.724(3) .
C8 C9 1.351(5) .
C8 H8 0.9500 .
C9 S2 1.716(4) .
C9 H9 0.9500 .
C10 N1 1.462(4) .
C10 C11 1.525(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.527(5) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.520(5) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.524(5) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.513(5) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
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
C2 C2 C3 N1 0.8(4) 2_667
C1 C2 C3 N1 -178.7(4) 2_667
C2 C2 C3 C4 -179.7(3) 2_667
C1 C2 C3 C4 0.8(6) 2_667
C2 C3 C4 C5 -5.6(5) .
N1 C3 C4 C5 173.8(3) .
C2 C3 C4 S1 173.1(2) .
N1 C3 C4 S1 -7.5(5) .
C3 C4 C5 C6 179.7(3) .
S1 C4 C5 C6 0.8(3) .
C4 C5 C6 C7 -0.3(4) .
C4 C5 C6 S2 177.6(3) .
C5 C6 C7 C8 179.0(3) .
S2 C6 C7 C8 0.6(4) .
C5 C6 C7 S1 -0.3(3) .
S2 C6 C7 S1 -178.73(16) .
C6 C7 C8 C9 -0.4(4) .
S1 C7 C8 C9 178.7(3) .
C7 C8 C9 S2 0.0(4) .
N1 C10 C11 C12 173.3(3) .
C10 C11 C12 C13 -79.4(4) .
C11 C12 C13 C14 -175.6(3) .
C12 C13 C14 C15 170.0(3) .
C2 C3 N1 C1 -1.7(3) .
C4 C3 N1 C1 178.8(3) .
C2 C3 N1 C10 178.7(3) .
C4 C3 N1 C10 -0.8(5) .
O1 C1 N1 C3 -177.2(3) .
C2 C1 N1 C3 1.8(3) 2_667
O1 C1 N1 C10 2.5(4) .
C2 C1 N1 C10 -178.5(2) 2_667
C11 C10 N1 C3 88.4(4) .
C11 C10 N1 C1 -91.2(3) .
C6 C7 S1 C4 0.6(2) .
C8 C7 S1 C4 -178.5(4) .
C5 C4 S1 C7 -0.8(2) .
C3 C4 S1 C7 -179.7(3) .
C8 C9 S2 C6 0.3(3) .
C7 C6 S2 C9 -0.5(2) .
C5 C6 S2 C9 -178.5(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339987
