Substituent-induced modulation of proaromaticity in benzo-fused fluorenophenalene exhibiting low-lying LUMO
Sahewal, Sakshi; Sharma, Suman; Mallick, Dibyendu; Das, Soumyajit; Chemical Communications  (2026) –; doi:10.1039/D6CC01746K

data_7135752
_publ_section_title
;
 Substituent-induced modulation of proaromaticity in benzo-fused
 fluorenophenalene exhibiting a low-lying LUMO.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9481
_journal_page_last               9485
_journal_paper_doi               10.1039/d6cc01746k
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C48 H40 O'
_chemical_formula_sum            'C48 H40 O'
_chemical_formula_weight         632.80
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2026-03-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                96.376(8)
_cell_angle_beta                 93.001(5)
_cell_angle_gamma                98.414(5)
_cell_formula_units_Z            4
_cell_length_a                   9.0236(14)
_cell_length_b                   16.688(3)
_cell_length_c                   26.510(5)
_cell_measurement_reflns_used    6073
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.29
_cell_volume                     3915.1(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.1075
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23803
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.877
_diffrn_reflns_theta_min         1.866
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1194 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.6980.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic brownish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.074
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344.0
_exptl_crystal_recrystallization_method
'slow solvent diffusion of methanol into dichloromethane'
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     897
_refine_ls_number_reflns         14461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1624
_refine_ls_R_factor_gt           0.0905
_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^)+(0.0792P)^2^+2.6433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2061
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7314
_reflns_number_total             15178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01746k2.cif
_cod_data_source_block           ss_181r_0ma_a
_cod_depositor_comments          'Adding full bibliography for 7135752.cif.'
_cod_database_code               7135752
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.958
_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:
 C2(H2A,H2B), C2'(H2'A,H2'B)
2.b Aromatic/amide H refined with riding coordinates:
 C43(H43), C37(H37), C24(H24), C10(H10), C9(H9), C8(H8), C11(H11), C13(H13),
 C46(H46), C31(H31), C32(H32), C33(H33), C34(H34), C27(H27), C18(H18), C4(H4),
 C5(H5), C24'(H24'), C18'(H18'), C43'(H43'), C27'(H27'), C46'(H46'), C13'(H13'),
  C8'(H8'), C9'(H9'), C10'(H10'), C11'(H11'), C5'(H5'), C4'(H4'), C37'(H37'),
 C34'(H34'), C33'(H33'), C32'(H32'), C31'(H31')
2.c Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C26(H26A,H26B,H26C), C42(H42A,H42B,H42C), C48(H48A,H48B,
 H48C), C29(H29A,H29B,H29C), C23(H23A,H23B,H23C), C1(H1A,H1B,H1C), C26'(H26D,
 H26E,H26F), C45'(H45D,H45E,H45F), C42'(H42D,H42E,H42F), C48'(H48D,H48E,H48F),
 C1'(H1'A,H1'B,H1'C), C23'(H23D,H23E,H23F), C29'(H29D,H29E,H29F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              46753
_shelx_fab_checksum              51286
_olex2_submission_special_instructions 'No special instructions were received'