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_4123748
_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         'C70 H66'
_chemical_formula_sum            'C70 H66'
_chemical_formula_weight         907.22
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                111.777(4)
_cell_angle_beta                 90.520(5)
_cell_angle_gamma                90.037(5)
_cell_formula_units_Z            4
_cell_length_a                   12.8654(8)
_cell_length_b                   18.9405(10)
_cell_length_c                   24.2937(14)
_cell_measurement_reflns_used    4268
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      53.29
_cell_measurement_theta_min      4.67
_cell_volume                     5497.1(6)
_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 0.671
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.1141
_diffrn_reflns_laue_measured_fraction_full 0.671
_diffrn_reflns_laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26872
_diffrn_reflns_point_group_measured_fraction_full 0.671
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         54.486
_diffrn_reflns_theta_min         4.670
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.5920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0861 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.7886.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dull reddish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_description       plate
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1336
_refine_ls_number_reflns         12611
_refine_ls_number_restraints     1735
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.1022
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2703
_refine_ls_wR_factor_ref         0.3150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8660
_reflns_number_total             12611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b03074_si_001.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 4123748--4123750.cif.'
_cod_database_code               4123748
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C66A-C65A \\sim C65A-C1F \\sim C66-C65A \\sim C65A-C1C \\sim C67-C65A \\sim
C67A-C65A
 with sigma of 0.02
 C66A-C65A \\sim C65A-C1C \\sim C67-C65A \\sim C66-C65A \\sim C65A-C1F \\sim
C67A-C65A
 with sigma of 0.02
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
 Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(H1FC)=Sof(C66A)=Sof(H66D)=Sof(H66E)=
 Sof(H66F)=Sof(C67A)=Sof(H67D)=Sof(H67E)=Sof(H67F)=1-FVAR(1)
 Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=
 Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(H67C)=FVAR(1)
 Sof(C1G)=Sof(H1GA)=Sof(H1GB)=Sof(H1GC)=Sof(C17A)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=Sof(C1H)=Sof(H1HA)=Sof(H1HB)=Sof(H1HC)=1-FVAR(2)
 Sof(C121)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=
 Sof(H1AC)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(H1EC)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C16(H16), C17(H17), C18(H18), C21(H21), C23(H23), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C34(H34), C36(H36), C38(H38), C45(H45),
  C46(H46), C49(H49), C51(H51), C52(H52), C54(H54), C55(H55), C56(H56),
 C57(H57), C58(H58), C60(H60), C61(H61), C62(H62), C63(H63), C64(H64), C71(H71),
  C76(H76), C78(H78), C83(H83), C84(H84), C85(H85), C86(H86), C87(H87),
 C88(H88), C94(H94), C99(H99), C100(H100), C101(H101), C102(H102), C103(H103),
 C104(H104), C105(H105), C107(H107), C109(H109), C111(H111), C120(H120),
 C122(H122), C128(H128), C130(H130), C131(H131), C132(H132), C133(H133),
 C134(H134), C135(H135), C136(H136)
6.b Fitted hexagon refined as free rotating group:
 C53(C52,C54,C55,C56,C57)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C40(H40A,H40B,
 H40C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C66(H66A,
 H66B,H66C), C113(H11A,H11B,H11C), C114(H11D,H11E,H11F), C115(H11G,H11H,H11I),
 C117(H11J,H11K,H11L), C118(H11M,H11N,H11O), C119(H11P,H11Q,H11R), C121(H12A,
 H12B,H12C), C125(H12D,H12E,H12F), C126(H12G,H12H,H12I), C127(H12J,H12K,H12L),
 C1A(H1AA,H1AB,H1AC), C1C(H1CA,H1CB,H1CC), C1B(H1BA,H1BB,H1BC), C1D(H1DA,H1DB,
 H1DC), C1F(H1FA,H1FB,H1FC), C66A(H66D,H66E,H66F), C1E(H1EA,H1EB,H1EC),
 C1G(H1GA,H1GB,H1GC), C17A(H17A,H17B,H17C), C1H(H1HA,H1HB,H1HC), C67(H67A,H67B,
 H67C), C67A(H67D,H67E,H67F)
;
_olex2_computing_structure_refinement_long 'SHELXL-97 (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'