Shedding new light on quadrupolar 1,4-dihydropyrrolo[3,2-<i>b</i>]pyrroles: impact of electron-deficient scaffolds over emission.
Szymański, Bartosz; Sahoo, Smruti Ranjan; Vakuliuk, Olena; Valiev, Rashid; Ramazanov, Ruslan; Łaski, Piotr; Jarzembska, Katarzyna N.; Kamiński, Radosław; Teimouri, Mohammad B.; Baryshnikov, Glib; Gryko, Daniel T.; Chemical science 16 (2025) 2170–2179; doi:10.1039/d4sc07275h

data_1573447
_publ_section_title
;
 Shedding new light on quadrupolar
 1,4-dihydropyrrolo[3,2-<i>b</i>]pyrroles: impact of electron-deficient
 scaffolds over emission.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              2170
_journal_page_last               2179
_journal_paper_doi               10.1039/d4sc07275h
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C54 H66 N6 S2'
_chemical_formula_sum            'C54 H66 N6 S2'
_chemical_formula_weight         863.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
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_atom_sites_solution_hydrogens   geom
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;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
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_audit_update_record
;
2024-06-02 deposited with the CCDC.	2024-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_formula_units_Z            2
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_cell_length_b                   5.7949(2)
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_cell_measurement_reflns_used    4390
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.0040
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_cell_volume                     2379.3(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
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_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19841
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.736
_diffrn_reflns_theta_min         3.505
_exptl_absorpt_coefficient_mu    1.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             928
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_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.033
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_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0634
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0829P)^2^+1.0661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.1972
_reflns_number_gt                3337
_reflns_number_total             4943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07275h2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 1573442--1573448.cif.'
_cod_database_code               1573447
_shelx_shelxl_version_number     2018/3
_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:
 C21(H21A,H21B), C22(H22A,H22B), C20(H20A,H20B), C23(H23A,H23B), C24(H24A,
 H24B), C27(H27A,H27B), C26(H26A,H26B), C25(H25A,H25B), C28(H28A,H28B),
 C29(H29A,H29B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C3(H3), C6(H6), C18(H18), C19(H19), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_shelx_res_checksum              85637
_olex2_submission_special_instructions 'No special instructions were received'