Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols.
Arimitsu, Satoru; Jacobsen, Jesse M.; Hammond, Gerald B.; The Journal of organic chemistry 73 (2008) 2886–2889; doi:10.1021/jo800088y

data_4029570
_publ_section_title
;
 Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential
 iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2886
_journal_page_last               2889
_journal_paper_doi               10.1021/jo800088y
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C16 H11 F2 I O'
_chemical_formula_sum            'C16 H11 F2 I O'
_chemical_formula_weight         384.15
_chemical_name_common
; 
 3,3-difluoro-4-iodo-2,5-diphenyl-2,3-dihydrofuran
;
_chemical_name_systematic
; 
 3,3-difluoro-4-iodo-2,5-diphenyl-2,3-dihydrofuran
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             Aug_13_2007
_audit_creation_method           SHELXL-97
_audit_update_record
;
Aug_29_2007 text and data added by Mark S. Mashuta
Oct_08_2007 text added by Mark S. Mashuta
Dec_07_2007 text added by Mark S. Mashuta
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.837(4)
_cell_length_b                   14.112(3)
_cell_length_c                   5.1834(10)
_cell_measurement_reflns_used    6836
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.143
_cell_measurement_theta_min      2.509
_cell_volume                     1451.0(5)
_computing_cell_refinement       'SAINT 6.36 (Bruker, 2002)'
_computing_data_collection       'SMART 5.628 (Bruker, 2002)'
_computing_data_reduction        'SAINT 6.36 (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker, 2001)'
_computing_publication_material  'SHELXTL 6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-90 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       \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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13948
_diffrn_reflns_theta_full        27.61
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.221
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_correction_T_min  0.506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Absorption correction was based upon symmetry equivalent and
repeated intensity measurements using the program SADABS
(Sheldrick, 2001).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0341P)^2^+0.9261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                2509
_reflns_number_total             3172
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo800088y-file003.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1451.1(5)
_cod_database_code               4029570