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_7112478
_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_sum            'C25 H18 O2'
_chemical_formula_weight         350.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.273(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0032(12)
_cell_length_b                   11.3220(11)
_cell_length_c                   13.1801(13)
_cell_measurement_reflns_used    5245
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.40
_cell_volume                     1750.2(3)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 'BRUKER SMART'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8369
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0788P)^2^+0.8652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1428
_reflns_number_gt                2729
_reflns_number_total             3086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc00378k2.cif
_cod_data_source_block           530ajm
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7112478