Molecular iodine-mediated reaction of 2-(2-phenylethynyl)-Morita-Baylis-Hillman adducts: an easy route to naphthyl ketones and iodo-substituted isochromenes.
Janreddy, Donala; Kavala, Veerababurao; Kotipalli, Trimurtulu; Rajawinslin, R. R.; Kuo, Chun-Wei; Huang, Wen-Chang; Yao, Ching-Fa; Organic & biomolecular chemistry 12 (2014) 8247–8256; doi:10.1039/c4ob00938j

data_7154000
_publ_section_title
;
 Molecular iodine-mediated reaction of
 2-(2-phenylethynyl)-Morita-Baylis-Hillman adducts: an easy route to
 naphthyl ketones and iodo-substituted isochromenes.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8247
_journal_page_last               8256
_journal_paper_doi               10.1039/c4ob00938j
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C19 H14 O3'
_chemical_formula_sum            'C19 H14 O3'
_chemical_formula_weight         290.30
_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                86.924(3)
_cell_angle_beta                 69.716(2)
_cell_angle_gamma                76.474(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3228(8)
_cell_length_b                   8.8321(9)
_cell_length_c                   10.8845(11)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     729.33(13)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.1362
_diffrn_reflns_av_sigmaI/netI    0.0940
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5654
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_correction_T_min  0.9444
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1004P)^2^+0.0237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1764
_reflns_number_gt                2123
_reflns_number_total             2524
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00938j2.cif
_cod_data_source_block           a12599
_cod_depositor_comments
'Adding full bibliography for 7154000--7154003.cif.'
_cod_database_code               7154000