Tandem Friedel-Crafts Annulation to Novel Perylene Analogues
Mark A. Penick; Mathew P. D. Mahindaratne; Robert D. Gutierrez; Terrill D. Smith; Edward R. T. Tiekink; George R. Negrete; Journal of Organic Chemistry 73 (2008) 6378–6381; doi:10.1021/jo800558c

data_4023595
_publ_section_title
;
 Tandem Friedel-Crafts Annulation to Novel Perylene Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6378
_journal_page_last               6381
_journal_paper_doi               10.1021/jo800558c
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C36 H52 O2'
_chemical_formula_sum            'C36 H52 O2'
_chemical_formula_weight         516.78
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.869(5)
_cell_angle_beta                 95.234(10)
_cell_angle_gamma                103.709(9)
_cell_formula_units_Z            1
_cell_length_a                   4.608(2)
_cell_length_b                   9.424(4)
_cell_length_c                   17.933(7)
_cell_measurement_reflns_used    2542
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      40.8
_cell_measurement_theta_min      2.5
_cell_volume                     752.8(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  AFC12\K/SATURN724
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3931
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.080
_refine_ls_R_factor_gt           0.072
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1166P)^2^+0.2066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.197
_refine_ls_wR_factor_ref         0.208
_reflns_number_gt                2234
_reflns_number_total             2583
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo800558c-file002.cif
_cod_data_source_block           680051
_cod_database_code               4023595