Rapid Access to Halohydrofurans via Brønsted Acid-Catalyzed Hydroxylation/Halocyclization of Cyclopropyl Methanols with Water and Electrophilic Halides
Srinivasa Reddy Mothe; Prasath Kothandaraman; Weidong Rao; Philip Wai Hong Chan; Journal of Organic Chemistry 76 (2011) 2521–2531; doi:10.1021/jo102374z

data_4026195
_publ_section_title
;
 Rapid Access to Halohydrofurans via Br\/onsted Acid-Catalyzed
 Hydroxylation/Halocyclization of Cyclopropyl Methanols with Water and
 Electrophilic Halides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2521
_journal_page_last               2531
_journal_paper_doi               10.1021/jo102374z
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H15 I O'
_chemical_formula_sum            'C18 H15 I O'
_chemical_formula_weight         374.20
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 101.5430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.19670(10)
_cell_length_b                   9.8216(2)
_cell_length_c                   9.2868(2)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      54.36
_cell_measurement_theta_min      2.24
_cell_volume                     732.51(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44886
_diffrn_reflns_theta_full        56.62
_diffrn_reflns_theta_max         56.62
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    2.178
_exptl_absorpt_correction_T_max  0.8116
_exptl_absorpt_correction_T_min  0.6012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.084
_refine_diff_density_min         -1.453
_refine_diff_density_rms         0.373
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.591(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         15879
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0212
_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^)+(0.0278P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0501
_refine_ls_wR_factor_ref         0.0579
_reflns_number_gt                14092
_reflns_number_total             15879
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102374z_si_002.cif
_cod_data_source_block           chan78s
_cod_database_code               4026195