Structural chemistry and environment-dependent fluorescence of a tetratopic pyrrolo[3,2-b]pyrrole ligand
Brown, Corey L.; Elliott, Scarlett H.; Woodfine, Sian E.; Hawes, Chris S.; CrystEngComm 27 (2025) 7358–7366; doi:10.1039/D5CE00926J

data_7251119
_publ_section_title
;
 Structural chemistry and environment-dependent fluorescence of a
 tetratopic pyrrolo[3,2-b]pyrrole ligand
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7358
_journal_page_last               7366
_journal_paper_doi               10.1039/D5CE00926J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C36 H26 N2 O8, 4(C4 H9 N O)'
_chemical_formula_sum            'C52 H62 N6 O12'
_chemical_formula_weight         963.07
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-09-14 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                96.883(4)
_cell_angle_beta                 92.383(4)
_cell_angle_gamma                93.239(3)
_cell_formula_units_Z            1
_cell_length_a                   6.0160(6)
_cell_length_b                   10.8276(10)
_cell_length_c                   18.939(2)
_cell_measurement_reflns_used    2316
_cell_measurement_temperature    150.9
_cell_measurement_theta_max      27.023
_cell_measurement_theta_min      3.053
_cell_volume                     1221.4(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11605
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.702
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0550 before and 0.0488 after correction. The Ratio of minimum to maximum transmission is 0.9358. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4775
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0466P)^2^+0.5582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2913
_reflns_number_total             4775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00926j2.cif
_cod_data_source_block           L1-4DMA
_cod_depositor_comments
'Adding full bibliography for 7251119--7251122.cif.'
_cod_original_cell_volume        1221.3(2)
_cod_database_code               7251119
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.972
_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, All O(H) groups
2. Restrained distances
 O1-H1 = O3-H3
 0.84 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14), C16(H16),
 C17(H17)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              47500
_olex2_submission_special_instructions 'No special instructions were received'