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_1573444
_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 H64 N8 O6'
_chemical_formula_sum            'C54 H64 N8 O6'
_chemical_formula_weight         921.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 90.519(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   47.3727(18)
_cell_length_b                   10.9462(5)
_cell_length_c                   9.5717(4)
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    120
_cell_measurement_theta_max      70.1840
_cell_measurement_theta_min      3.7300
_cell_volume                     4963.2(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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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  0.1513
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            53952
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.429
_diffrn_reflns_theta_min         3.732
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.256
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       plate
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0620P)^2^+0.8717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1579
_reflns_number_gt                2975
_reflns_number_total             4929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07275h2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 1573442--1573448.cif.'
_cod_database_code               1573444
_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:
 C29(H29A,H29B), C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C26(H26A,
 H26B), C31(H31A,H31B), C28(H28A,H28B), C30(H30A,H30B), C32(H32A,H32B),
 C23(H23A,H23B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C19(H19), C18(H18), C13(H13), C16(H16), C15(H15), C12(H12)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;
_shelx_res_checksum              64307
_olex2_submission_special_instructions 'No special instructions were received'