A phosphine-mediated reaction of cyclic 1,2-diones and 3-alkyl allenoates: an efficient protocol for benzannulation applicable to the synthesis of polycyclic aromatic hydrocarbons
Anu Jose; Jayakrishnan A.J.; Balaraman Vedhanarayanan; Rajeev S.Menon; Sunil Varughese; Eringathodi Suresh; Vijay Nair; Chem.Commun. 50 (2014) 4616–; doi:10.1039/C4CC00378K

data_7112479
_publ_section_title
;
 A phosphine-mediated reaction of cyclic 1,2-diones and 3-alkyl
 allenoates: an efficient protocol for benzannulation applicable to the
 synthesis of polycyclic aromatic hydrocarbons
;
_journal_name_full               Chem.Commun.
_journal_page_first              4616
_journal_paper_doi               10.1039/C4CC00378K
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C29 H20 O2'
_chemical_formula_sum            'C29 H20 O2'
_chemical_formula_weight         400.45
_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                93.436(6)
_cell_angle_beta                 100.301(11)
_cell_angle_gamma                118.186(9)
_cell_formula_units_Z            2
_cell_length_a                   9.365(7)
_cell_length_b                   9.614(7)
_cell_length_c                   13.398(10)
_cell_measurement_reflns_used    1361
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1031.5(13)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1990)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8513
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1997'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                2014
_reflns_number_total             4148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc00378k2.cif
_cod_data_source_block           datam
_cod_original_cell_volume        1031.4(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7112479