Cyclopenta-fused polyaromatic hydrocarbons: synthesis and characterisation of a stable, carbon-centred helical radical
Herzog, Stefan; Hinz, Alexander; Breher, Frank; Podlech, Joachim; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00172A

data_7158589
_publ_section_title
;
 Cyclopenta-fused polyaromatic hydrocarbons: synthesis and
 characterisation of a stable, carbon-centred helical radical
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00172A
_journal_year                    2022
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C54 H45, 0.75 (C H Cl3)'
_chemical_formula_sum            'C54.75 H45.75 Cl2.25'
_chemical_formula_weight         783.42
_chemical_melting_point          514
_chemical_name_systematic
'5,8,11-trimesityl-cyclopenta[1,2-c:4,3-c']difluorene radical'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-20 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.088(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.2500(7)
_cell_length_b                   25.6491(8)
_cell_length_c                   17.0445(6)
_cell_measurement_reflns_used    17286
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      1.31
_cell_volume                     8547.6(5)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction
;
X-Area Integrate 1.73.0.0 (STOE, 2018)
X-Area LANA 1.72.3.0 (STOE, 2018)
;
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.82, Darmstadt 2018
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      ' 130 frames, detector distance = 110 mm'
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35392
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.310
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             3300
_exptl_crystal_recrystallization_method
'dissolved in CHCl3, frozen, covered with EtOH, slow diffusion'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1401
_refine_ls_number_reflns         15869
_refine_ls_number_restraints     2470
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1428
_refine_ls_R_factor_gt           0.0712
_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^)+(0.0753P)^2^+6.8427P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8680
_reflns_number_total             15869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00172a2.cif
_cod_data_source_block           SH156_2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158589
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              24610