5,10-Dimesityldiindeno[1,2-a:2',1'-i]phenanthrene: A Stable Biradicaloid Derived from Chichibabin’s Hydrocarbon
Majewski, Marcin Aleksander; Chmielewski, Piotr Jan; Chien, Alan; Hong, Yongseok; Lis, Tadeusz; Witwicki, Maciej; Kim, Dongho; Zimmerman, Paul; Stępień, Marcin; Chemical Science  (2019) –; doi:10.1039/C9SC00170K

data_1550578
_publ_section_title
;
 5,10-Dimesityldiindeno[1,2-a:2',1'-i]phenanthrene: A Stable Biradicaloid
 Derived from Chichibabin&#x2019;s Hydrocarbon
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00170K
_journal_year                    2019
_chemical_formula_moiety         'C46 H36, C6 H14'
_chemical_formula_sum            'C52 H50'
_chemical_formula_weight         674.92
_chemical_name_systematic
;
 5,10-dimesityldiindeno[1,2-a:2',1'-i]phenanthrene
;
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-08-09 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.63(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.156(4)
_cell_length_b                   11.811(3)
_cell_length_c                   20.079(5)
_cell_measurement_reflns_used    2278
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      57.2
_cell_measurement_theta_min      2.8
_cell_volume                     3823.8(17)
_computing_cell_refinement
'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_collection
'CrysAlis CCD; Oxford-Diffraction Poland, 2003'
_computing_data_reduction
'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, ccd camera Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.1206
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14622
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         27.057
_diffrn_reflns_theta_min         2.895
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       plate
_exptl_crystal_F_000             1448
_exptl_crystal_preparation       'Magnetic properties'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         8330
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1710
_refine_ls_R_factor_gt           0.0825
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+1.1861P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4224
_reflns_number_total             8330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00170k3.cif
_cod_data_source_block           MM7
_cod_database_code               1550578
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-2
_shelx_res_checksum              5980