Reactive Iron Carbonyl Reagents via Reaction of Metal Alkoxides with Fe(CO)5 or Fe2(CO)9: Synthesis of Cyclobutenediones via Double Carbonylation of Alkynes
Mallesh Beesu; Mariappan Periasamy; Journal of Organic Chemistry 76 (2011) 543–549; doi:10.1021/jo102104a

data_4025992
_publ_contact_author_address
; 
School of Chemistry
University of Hyderabad
Hyderabad 500 046,
India
;
_publ_contact_author_email       mpsc@uohyd.ernet.in
_publ_section_title
;
 Reactive Iron Carbonyl Reagents via Reaction of Metal Alkoxides with
 Fe(CO)5 or Fe2(CO)9: Synthesis of Cyclobutenediones via Double
 Carbonylation of Alkynes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              543
_journal_page_last               549
_journal_paper_doi               10.1021/jo102104a
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C18 H10 O2'
_chemical_formula_sum            'C18 H10 O2'
_chemical_formula_weight         258.26
_chemical_melting_point          116
_chemical_name_common            3-Phenyl-4-phenylethynyl-1,2-cyclobutenedione
_chemical_name_systematic
; 
 ? 
;
_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                 97.6640(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7943(8)
_cell_length_b                   15.0340(11)
_cell_length_c                   7.5926(5)
_cell_measurement_temperature    298(2)
_cell_volume                     1334.26(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Phi and Omega 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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10070
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9626
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       Block'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0783P)^2^+0.1711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                1743
_reflns_number_total             2596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102104a_si_003_1.cif
_cod_data_source_block           mp138_m
_cod_database_code               4025992