Contorted aromatics via a palladium-catalyzed cyclopentannulation strategy
Sambasiva R. Bheemireddy; Pamela C. Ubaldo; Aaron D. Finke; Lichang Wang; Kyle N. Plunkett; Journal of Materials Chemistry C 4 (2016) 3963–3969; doi:10.1039/C5TC02305J

data_7234720
_publ_section_title
;
 Contorted aromatics via a palladium-catalyzed cyclopentannulation
 strategy
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3963
_journal_page_last               3969
_journal_paper_doi               10.1039/C5TC02305J
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         '2(C46 H30 O4)'
_chemical_formula_sum            'C92 H60 O8'
_chemical_formula_weight         1293.40
_chemical_name_systematic
2,7,13,18-tetramethoxytetrabenzo[f,h,r,t]rubicene
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 122.05(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   37.950(8)
_cell_length_b                   3.8000(8)
_cell_length_c                   23.960(5)
_cell_measurement_temperature    100
_cell_volume                     2928.6(14)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'X10SA, Swiss Light Source'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.61933
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            40294
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.255
_diffrn_reflns_theta_min         1.103
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0716 before and 0.0541 after correction.
The Ratio of minimum to maximum transmission is 0.9035.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0547
_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^)+(0.1010P)^2^+2.4670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4165
_reflns_number_total             4452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-3963.cif
_cod_data_source_block           plunkett_2_merged_a
_cod_original_cell_volume        2928.7(13)
_cod_database_code               7234720
_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.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00F), C00P(H00G,H00M,H00N)
;
_shelx_res_checksum              75435
_shelx_hkl_checksum              88768
_olex2_submission_special_instructions 'No special instructions were received'