A Simple and Mild Synthesis of 1H-Isochromenes and (Z)-1-Alkylidene-1,3-dihydroisobenzofurans by the Iodocyclization of 2-(1-Alkynyl)benzylic Alcohols
Raffaella Mancuso; Saurabh Mehta; Bartolo Gabriele; Giuseppe Salerno; William S. Jenks; Richard C. Larock; Journal of Organic Chemistry 75 (2010) 897–901; doi:10.1021/jo902333y

data_4025197
_publ_contact_author_address
'Department of Chemistry, Iowa State University, Ames, Iowa 50011 USA'
_publ_contact_author_name        'Richard C. Larock'
_publ_section_title
;
 A Simple and Mild Synthesis of 1H-Isochromenes and
 (Z)-1-Alkylidene-1,3-dihydroisobenzofurans by the Iodocyclization of
 2-(1-Alkynyl)benzylic Alcohols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              897
_journal_page_last               901
_journal_paper_doi               10.1021/jo902333y
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C16 H13 I O2'
_chemical_formula_weight         364.16
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.537(7)
_cell_length_b                   14.916(7)
_cell_length_c                   7.794(4)
_cell_measurement_reflns_used    878
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      3.44
_cell_volume                     1341.2(12)
_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      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_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  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11635
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    2.382
_exptl_absorpt_correction_T_max  0.5987
_exptl_absorpt_correction_T_min  0.4894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.741
_refine_diff_density_min         -1.366
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3282
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0658P)^2^+3.0954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                2620
_reflns_number_total             3282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902333y_si_002.cif
_cod_data_source_block           lar29
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1341.2(13)
_cod_database_code               4025197