Synthesis of Dibenzo[g,p]chrysenes from Bis(biaryl)acetylenes via Sequential ICl-Induced Cyclization and Mizoroki-Heck Coupling
Chia-Wen Li; Cheng-I Wang; Hsin-Yi Liao; Rupsha Chaudhuri; Rai-Shung Liu; Journal of Organic Chemistry 72 (2007) 9203–9207; doi:10.1021/jo701504m

data_4023027
_publ_section_title
;
 Synthesis of Dibenzo[g,p]chrysenes from Bis(biaryl)acetylenes
 via Sequential ICl-Induced Cyclization and Mizoroki-Heck Coupling
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9203
_journal_page_last               9207
_journal_paper_doi               10.1021/jo701504m
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C22 H17 I O3'
_chemical_formula_weight         456.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.424(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8190(7)
_cell_length_b                   9.8363(7)
_cell_length_c                   18.3221(12)
_cell_measurement_temperature    295(2)
_cell_volume                     1948.1(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_av_sigmaI/netI    0.3250
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14200
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    1.661
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.520
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.520
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0199P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0685
_reflns_number_gt                1364
_reflns_number_total             4836
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701504m-File005.cif
_cod_data_source_block           jl12m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023027