Reversible formation of tetraphenylpentalene, a room temperature stable antiaromatic hydrocarbon.
Sanderson, Hugh J.; Helbig, Andreas; Kociok-Köhn, Gabriele; Helten, Holger; Hintermair, Ulrich; Chemical science 16 (2025) 952–961; doi:10.1039/d4sc06439a

data_1573269
_publ_section_title
;
 Reversible formation of tetraphenylpentalene, a room temperature stable
 antiaromatic hydrocarbon.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              952
_journal_page_last               961
_journal_paper_doi               10.1039/d4sc06439a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         '2(C64 H44), C32 H22, C6 H13'
_chemical_formula_sum            'C166 H123'
_chemical_formula_weight         2117.64
_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_method           SHELXL-2018/3
_audit_update_record
;
2024-02-26 deposited with the CCDC.	2024-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.309(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   43.6143(9)
_cell_length_b                   10.5720(2)
_cell_length_c                   25.1335(7)
_cell_measurement_reflns_used    8784
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.5990
_cell_measurement_theta_min      4.7130
_cell_volume                     11467.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_computing_structure_refinement
;
 SHELXL-2018/3 (Sheldrick, 2018)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_structure_solution
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_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  0.0570
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            49934
_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         73.064
_diffrn_reflns_theta_min         4.306
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             4476
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     778
_refine_ls_number_reflns         11373
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0432P)^2^+6.0821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8627
_reflns_number_total             11373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06439a6.cif
_cod_data_source_block           s21uh10
_cod_depositor_comments          'Adding full bibliography for 1573269.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1573269
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.868
_shelx_estimated_absorpt_t_max   0.990
_oxdiff_exptl_absorpt_empirical_full_min 0.667
_oxdiff_exptl_absorpt_empirical_full_max 1.278
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              5501
_shelx_hkl_checksum              40997