Structure-property relationships in unsymmetric bis(antiaromatics): Who wins the battle between pentalene and benzocyclobutadiene?
Mayer, Péter J; El Bakouri, Ouissam; Holczbauer, Tamás; Samu, Gergely F.; Janáky, Csaba; Ottosson, Henrik; London, Gábor; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03119

data_4038146
_publ_section_title
;
 Structure-property relationships in unsymmetric bis(antiaromatics): Who
 wins the battle between pentalene and benzocyclobutadiene?
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03119
_journal_year                    2020
_chemical_formula_moiety         'C37 H24 O'
_chemical_formula_sum            'C37 H24 O'
_chemical_formula_weight         484.56
_chemical_name_systematic
;
1-(4-methoxyphenyl)-2,3-diphenylpentaleno[1,2-a]biphenylene
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 97.256(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2162(16)
_cell_length_b                   14.533(3)
_cell_length_c                   16.867(3)
_cell_measurement_reflns_used    18487
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      3.06
_cell_volume                     2484.2(8)
_computing_cell_refinement       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_data_collection       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_data_reduction        'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       RX
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1630
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18838
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        18.845
_diffrn_reflns_theta_max         18.845
_diffrn_reflns_theta_min         3.056
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.999168
_exptl_absorpt_correction_T_min  0.997982
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
T.Higashi, Numerical Absorption Correction, NUMABS, 2002
T.Higashi, Empirical Absorption Correction, 2001
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         1950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0688
_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^)+(0.0356P)^2^+2.2003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1367
_reflns_number_total             1950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03119_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2484.2(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038146
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              30531
_shelx_hkl_checksum              11564