The Impact of Antiaromatic Subunits in [4n+2] π-Systems: Bispentalenes with [4n+2] π-Electron Perimeters and Antiaromatic Character.
Cao, Jing; London, Gábor; Dumele, Oliver; von Wantoch Rekowski, Margarete; Trapp, Nils; Ruhlmann, Laurent; Boudon, Corinne; Stanger, Amnon; Diederich, François; Journal of the American Chemical Society 137 (2015) 7178–7188; doi:10.1021/jacs.5b03074

data_4123750
_publ_section_title
;
 The Impact of Antiaromatic Subunits in [4n+2] \p-Systems: Bispentalenes
 with [4n+2] \p-Electron Perimeters and Antiaromatic Character.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7178
_journal_page_last               7188
_journal_paper_doi               10.1021/jacs.5b03074
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C62 H44 O4, C H2 Cl2'
_chemical_formula_sum            'C63 H46 Cl2 O4'
_chemical_formula_weight         937.90
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.803(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.9753(9)
_cell_length_b                   15.4590(9)
_cell_length_c                   10.9343(8)
_cell_measurement_reflns_used    7572
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      26.89
_cell_measurement_theta_min      2.31
_cell_volume                     2312.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    OLEX2
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46889
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_min         1.489
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0485 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.9690.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear brownish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5332
_refine_ls_number_restraints     373
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0657P)^2^+2.0398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3571
_reflns_number_total             5332
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b03074_si_001.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 4123748--4123750.cif.'
_cod_database_code               4123750
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.970
_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. Restrained distances
 Cl2-C1A \\sim Cl1-C1A
 with sigma of 0.001
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: Cl1(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5) Cl2(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C)
;
_olex2_computing_structure_refinement_long 'SHELXL-97 (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'