Geometric Orthogonality as a Recipe for Efficient Intramolecular Charge Generation in Core Substituted NDI Derivatives
Britton, Hugh C.; Martin Santa Daria, Alberto; Lyu, Chao; Augusztin, Andras B.; Cowen, Lewis; Bucar, Dejan-Kresimir; Tabor, Alethea B.; Schroeder, Bob C.; Gómez, Sandra; Marin-Beloqui, Jose Marin; Chemical Science  (2026) –; doi:10.1039/D6SC00456C

data_1576979
_publ_section_title
;
 Geometric orthogonality as a recipe for efficient intramolecular charge
 generation in core substituted NDI derivatives.
;
_journal_issue                   20
_journal_name_full               'Chemical science'
_journal_page_first              10133
_journal_page_last               10144
_journal_paper_doi               10.1039/d6sc00456c
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C28 H18 N2 O8 S2, 2(C4 H8 O)'
_chemical_formula_sum            'C36 H34 N2 O10 S2'
_chemical_formula_weight         718.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-12-31 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.1850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.9774(2)
_cell_length_b                   5.86680(10)
_cell_length_c                   21.8939(3)
_cell_measurement_reflns_used    21414
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      77.8870
_cell_measurement_theta_min      3.9250
_cell_volume                     1666.55(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            34051
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.542
_diffrn_reflns_theta_max         66.542
_diffrn_reflns_theta_min         3.924
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.982
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0336
_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/[\s^2^(Fo^2^)+(0.0386P)^2^+0.6234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2543
_reflns_number_total             2925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc00456c2.cif
_cod_data_source_block           NDI-Th
_cod_depositor_comments
'Adding full bibliography for 1576979--1576982.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1576979
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              18015