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_1573443
_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      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_date             2024-04-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-02 deposited with the CCDC.	2024-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                92.8453(16)
_cell_angle_beta                 96.3218(15)
_cell_angle_gamma                95.0155(15)
_cell_formula_units_Z            1
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_cell_length_b                   8.26449(16)
_cell_length_c                   20.8251(4)
_cell_measurement_reflns_used    17440
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.9890
_cell_measurement_theta_min      4.2300
_cell_volume                     1158.70(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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  0.0401
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28235
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.140
_diffrn_reflns_theta_min         2.138
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.3085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                4411
_reflns_number_total             4819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07275h2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 1573442--1573448.cif.'
_cod_database_code               1573443
_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), C20(H20A,H20B), C23(H23A,H23B), C22(H22A,H22B), C25(H25A,
 H25B), C24(H24A,H24B), C27(H27A,H27B), C26(H26A,H26B), C28(H28A,H28B),
 C29(H29A,H29B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C19(H19), C15(H15), C18(H18), C16(H16), C12(H12), C13(H13), C11(H11)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_shelx_res_checksum              26338
_olex2_submission_special_instructions 'No special instructions were received'