Direct Preparation of 3-Iodochromenes from 3-Aryl- and 3-Alkyl-2-propyn-1-ols with Diaryliodonium Salts and NIS.
Sasaki, Teppei; Miyagi, Kotaro; Moriyama, Katsuhiko; Togo, Hideo; Organic letters 18 (2016) 944–; doi:10.1021/acs.orglett.5b03651

data_1542711
_publ_section_title
;
 Direct Preparation of 3-Iodochromenes from 3-Aryl- and
 3-Alkyl-2-propyn-1-ols with Diaryliodonium Salts and NIS.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              944
_journal_paper_doi               10.1021/acs.orglett.5b03651
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C15 H10 Br I O'
_chemical_formula_weight         413.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 91.919(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.603(4)
_cell_length_b                   10.723(5)
_cell_length_c                   16.702(8)
_cell_measurement_reflns_used    3426
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5576
_cell_measurement_theta_min      2.2574
_cell_volume                     1360.9(12)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6932
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.274
_exptl_absorpt_correction_T_max  0.42
_exptl_absorpt_correction_T_min  0.31
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.790
_refine_diff_density_min         -1.435
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+0.2098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2549
_reflns_number_total             3034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03651_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        1360.9(11)
_cod_database_code               1542711
_shelx_res_checksum              3015
_shelx_hkl_checksum              35202