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_7154003
_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 H15 I O2'
_chemical_formula_sum            'C19 H15 I O2'
_chemical_formula_weight         402.21
_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                 90.5910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2342(2)
_cell_length_b                   37.9905(8)
_cell_length_c                   10.4703(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     3275.16(12)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23291
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         1.07
_exptl_absorpt_coefficient_mu    1.960
_exptl_absorpt_correction_T_max  0.9435
_exptl_absorpt_correction_T_min  0.3492
_exptl_absorpt_correction_type   multi-san
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.321
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.321
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+3.7269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                5417
_reflns_number_total             5837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00938j2.cif
_cod_data_source_block           ch16312a
_cod_depositor_comments
'Adding full bibliography for 7154000--7154003.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154003