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_1573448
_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         'C46 H50 N6 O4'
_chemical_formula_sum            'C46 H50 N6 O4'
_chemical_formula_weight         750.92
_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   geom
_audit_creation_date             2024-06-02
_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                 102.848(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6530(2)
_cell_length_b                   17.7756(3)
_cell_length_c                   18.8818(4)
_cell_measurement_reflns_used    6960
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.9940
_cell_measurement_theta_min      3.4310
_cell_volume                     4140.47(13)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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  0.0753
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34642
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.403
_diffrn_reflns_theta_min         3.456
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70166
_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            orange
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         8612
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0726P)^2^+1.0064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                6035
_reflns_number_total             8612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07275h2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 1573442--1573448.cif.'
_cod_database_code               1573448
_shelx_shelxl_version_number     2018/3
_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. Uiso/Uaniso restraints and constraints
Uanis(C5B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C5B, C5A, C6B, C6A, C7A, C7B, C11A, C11B, C12B, C12A, C13A, C13B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(N10B)=Sof(O9B)=Sof(N8B)=Sof(O20B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=
 Sof(C11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=1-FVAR(1)
 Sof(N10A)=Sof(O9A)=Sof(N8A)=Sof(O20A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=
 Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=FVAR(1)
 Sof(C55B)=Sof(H55D)=Sof(H55E)=Sof(H55F)=Sof(C56B)=Sof(H56D)=Sof(H56E)=
 Sof(H56F)=Sof(C57B)=Sof(H57D)=Sof(H57E)=Sof(H57F)=1-FVAR(2)
 Sof(C55A)=Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C56A)=Sof(H56A)=Sof(H56B)=
 Sof(H56C)=Sof(C57A)=Sof(H57A)=Sof(H57B)=Sof(H57C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C12A(H12A), C13A(H13A), C6B(H6B), C12B(H12B), C13B(H13B), C3(H3),
 C32(H32), C35(H35), C15(H15), C42(H42), C41(H41), C44(H44), C48(H48), C19(H19),
  C46(H46), C17(H17)
5.b Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C54(H54A,H54B,
 H54C), C27(H27A,H27B,H27C), C52(H52A,H52B,H52C), C25(H25A,H25B,H25C), C24(H24A,
 H24B,H24C), C23(H23A,H23B,H23C), C55A(H55A,H55B,H55C), C56A(H56A,H56B,H56C),
 C57A(H57A,H57B,H57C), C55B(H55D,H55E,H55F), C56B(H56D,H56E,H56F), C57B(H57D,
 H57E,H57F)
;
_shelx_res_checksum              22803
_olex2_submission_special_instructions 'No special instructions were received'