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_4123749
_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         'C74 H76 O4, 6(C D Cl3)'
_chemical_formula_sum            'C80 H76 Cl18 D6 O4'
_chemical_formula_weight         1751.50
_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   mixed
_atom_sites_solution_primary     iterative
_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                 121.225(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.3401(9)
_cell_length_b                   10.9180(7)
_cell_length_c                   27.3803(15)
_cell_measurement_reflns_used    1737
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.55
_cell_volume                     4177.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            43845
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_min         2.246
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0526 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.9375. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       plate
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.449
_refine_diff_density_min         -1.450
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.435
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         8604
_refine_ls_number_restraints     626
_refine_ls_restrained_S_all      1.421
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0937
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1235P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2551
_refine_ls_wR_factor_ref         0.2868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5194
_reflns_number_total             8604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b03074_si_001.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 4123748--4123750.cif.'
_cod_database_code               4123749
_shelxl_version_number           2013-4
_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
 Cl17-Cl18
 2.931 with sigma of 0.02
 Cl17-Cl16
 2.931 with sigma of 0.02
 Cl18-Cl16
 2.931 with sigma of 0.02
 Cl1A-Cl16
 2.931 with sigma of 0.02
 Cl1A-Cl1B
 2.931 with sigma of 0.02
 Cl1B-Cl16
 2.931 with sigma of 0.02
 Cl1A-D7
 2.35 with sigma of 0.02
 Cl16-D7
 2.35 with sigma of 0.02
 C6-D6
 1.09 with sigma of 0.02
 Cl18-D6
 2.35 with sigma of 0.02
 D6-Cl17
 2.35 with sigma of 0.02
 Cl16-C7 = Cl16-C6 = Cl17-C6 = Cl1B-C7 = Cl18-C6 = Cl1A-C7
 1.776 with sigma of 0.02
 Cl16-D6
 2.35 with sigma of 0.02
 Cl1B-D7
 2.35 with sigma of 0.02
 C5-D5 = C7-D7
 1.09 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. Uiso/Uaniso restraints and constraints
Uanis(Cl17) = Uanis(Cl1B)
Uanis(Cl1A) = Uanis(Cl18)
Uanis(Cl5) = Uanis(Cl14)
Uanis(Cl8) = Uanis(Cl13)
Uanis(Cl7) = Uanis(Cl15)
Uanis(Cl1) = Uanis(Cl5)
Uanis(Cl7) = Uanis(Cl3)
Uanis(C1) = Uanis(C5)
5. 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
6. Others
 1*[Sof(Cl1)+Sof(Cl3)+Sof(Cl4)+Sof(C5)+Sof(D5)]+1*[Sof(Cl5)+Sof(Cl7)+Sof(Cl8)+
 Sof(C1)+Sof(D1)]+1*[Sof(Cl9)+Sof(Cl10)+Sof(Cl11)+Sof(C2)+Sof(D2)]+1*[Sof(Cl13)+
 Sof(Cl14)+Sof(Cl15)+Sof(C3)+Sof(D3)]=1 with esd of 0.001
 Sof(Cl1)=Sof(Cl3)=Sof(Cl4)=Sof(C5)=Sof(D5)=FVAR(1)
 Sof(Cl5)=Sof(Cl7)=Sof(Cl8)=Sof(C1)=Sof(D1)=FVAR(2)
 Sof(Cl9)=Sof(Cl10)=Sof(Cl11)=Sof(C2)=Sof(D2)=FVAR(3)
 Sof(Cl13)=Sof(Cl14)=Sof(Cl15)=Sof(C3)=Sof(D3)=FVAR(4)
 Sof(Cl1A)=Sof(Cl1B)=Sof(C7)=Sof(D7)=1-FVAR(5)
 Sof(Cl17)=Sof(Cl18)=Sof(C6)=Sof(D6)=FVAR(5)
7.a Free rotating group:
 Cl1(Cl3,Cl4,C5,D5), Cl5(Cl7,Cl8,C1,D1), Cl9(Cl10,Cl11,C2,D2), Cl13(Cl14,Cl15,
 C3,D3)
7.b Ternary CH refined with riding coordinates:
 C48(D48)
7.c Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B)
7.d Aromatic/amide H refined with riding coordinates:
 C74(H74), C76(H76), C82(H82), C99(H99), C108(H108), C127(H127), C133(H133),
 C137(H137), C155(H155), C157(H157), C178(H178), C200(H200)
7.e Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C67(H67A,H67B,H67C), C78(H78A,H78B,H78C), C106(H10A,H10B,
 H10C), C166(H16A,H16B,H16C), C181(H18A,H18B,H18C), C195(H19A,H19B,H19C),
 C4(H4A,H4B,H4C)
;
_olex2_computing_structure_refinement_long 'SHELXL-97 (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'