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_1573446
_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         'C32 H22 N6 O2'
_chemical_formula_sum            'C32 H22 N6 O2'
_chemical_formula_weight         522.56
_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                 105.599(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.4345(4)
_cell_length_b                   7.9786(2)
_cell_length_c                   13.6019(2)
_cell_measurement_reflns_used    4927
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.5390
_cell_measurement_theta_min      3.8860
_cell_volume                     2449.54(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2687
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -114.00 -21.00   1.00    5.41    --  -42.93 -38.00  90.00   93
  2  \w     34.00  82.00   1.00    5.41    --   42.93 -99.00-120.00   48
  3  \w     34.00  82.00   1.00    5.41    --   42.93 -99.00 120.00   48
  4  \w     21.00 114.00   1.00    5.41    --   42.93  38.00   0.00   93
  5  \w     34.00  82.00   1.00    5.41    --   42.93 -99.00  60.00   48
  6  \w     56.00 112.00   1.00   21.63    --  109.50-125.00  90.00   56
  7  \w     56.00 112.00   1.00   21.63    --  109.50-125.00  30.00   56
  8  \w     56.00 112.00   1.00   21.63    --  109.50-125.00  60.00   56
  9  \w     56.00 112.00   1.00   21.63    --  109.50-125.00-120.00   56
 10  \w     30.00  97.00   1.00   21.63    --  109.50 -94.00  90.00   67
 11  \w     30.00  97.00   1.00   21.63    --  109.50 -94.00 150.00   67
 12  \w    100.00 135.00   1.00   21.63    --  109.50  45.00-120.00   35
 13  \w     30.00  70.00   1.00   21.63    --  109.50 -94.00 -60.00   40
 14  \w    117.00 158.00   1.00   21.63    --  109.50  30.00  90.00   41
 15  \w     60.00  91.00   1.00   21.63    --  109.50-125.00 -60.00   31
 16  \w     57.00 100.00   1.00   21.63    --  109.50-125.00   0.00   43
 17  \w     74.00 127.00   1.00   21.63    --  109.50 -45.00 -30.00   53
 18  \w     24.00 153.00   1.00   21.63    --  109.50   0.00-120.00  129
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0206014000
_diffrn_orient_matrix_UB_12      0.1837028000
_diffrn_orient_matrix_UB_13      -0.0168540000
_diffrn_orient_matrix_UB_21      0.0325385000
_diffrn_orient_matrix_UB_22      0.0176528000
_diffrn_orient_matrix_UB_23      -0.0839898000
_diffrn_orient_matrix_UB_31      -0.0563456000
_diffrn_orient_matrix_UB_32      -0.0569607000
_diffrn_orient_matrix_UB_33      -0.0804674000
_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  0.0205
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7892
_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         76.075
_diffrn_reflns_theta_min         3.917
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.673
_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            orange
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0474P)^2^+1.9298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                2312
_reflns_number_total             2530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07275h2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 1573442--1573448.cif.'
_cod_original_cell_volume        2449.53(9)
_cod_database_code               1573446
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.842
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15), C13(H13), C19(H19), C6(H6), C12(H12), C16(H16), C18(H18)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              47513
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.831