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_7251121
_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, 2(C3 H7 N O)'
_chemical_formula_sum            'C42 H40 N4 O10'
_chemical_formula_weight         760.78
_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                82.324(2)
_cell_angle_beta                 82.077(2)
_cell_angle_gamma                85.923(2)
_cell_formula_units_Z            1
_cell_length_a                   5.9506(5)
_cell_length_b                   11.1443(8)
_cell_length_c                   13.9257(11)
_cell_measurement_reflns_used    3369
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      25.097
_cell_measurement_theta_min      2.978
_cell_volume                     905.17(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.1039
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23948
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.084
_diffrn_reflns_theta_min         2.222
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0671 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.9270.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       rod
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.2940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2160
_reflns_number_total             3596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00926j2.cif
_cod_data_source_block           L1-2DMF
_cod_depositor_comments
'Adding full bibliography for 7251119--7251122.cif.'
_cod_database_code               7251121
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.973
_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
 O3-H3
 0.84 with sigma of 0.02
 O1-H1
 0.84 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16), C19(H19)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              23210
_olex2_submission_special_instructions 'No special instructions were received'