Synthesis of Substituted Phenanthrene by Iron(III)-Catalyzed Intramolecular Alkyne-Carbonyl Metathesis
Krishnendu Bera; Soumen Sarkar; Swapnadeep Jalal; Umasish Jana; Journal of Organic Chemistry 77 (2012) 8780–8786; doi:10.1021/jo301371n

data_4027552
_publ_section_title
;
 Synthesis of Substituted Phenanthrene by Iron(III)-Catalyzed
 Intramolecular Alkyne-Carbonyl Metathesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8780
_journal_page_last               8786
_journal_paper_doi               10.1021/jo301371n
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C22 H16 O'
_chemical_formula_weight         296.35
_chemical_name_systematic
; 
 ? 
;
_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                 100.067(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9052(2)
_cell_length_b                   10.4099(3)
_cell_length_c                   15.6229(4)
_cell_measurement_reflns_used    4178
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.27
_cell_volume                     1586.11(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12878
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9139
_exptl_absorpt_correction_T_min  0.8721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       rectanguler
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0046(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0754P)^2^+0.2796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1502
_reflns_number_gt                2640
_reflns_number_total             3635
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301371n_si_001.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4027552