Synthesis of fluorinated fused benzofurans and benzothiophenes: Smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers and sulfides.
Ponce González, Julia; Edgar, Mark; Elsegood, Mark R. J.; Weaver, George W.; Organic & biomolecular chemistry 9 (2011) 2294–2305; doi:10.1039/c0ob00790k

data_7151749
_publ_section_title
;
 Synthesis of fluorinated fused benzofurans and benzothiophenes:
 Smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers
 and sulfides.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2294
_journal_page_last               2305
_journal_paper_doi               10.1039/c0ob00790k
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C23 H12 Br3 F2 N S3, 0.5(C7 H8)'
_chemical_formula_sum            'C26.5 H16 Br3 F2 N S3'
_chemical_formula_weight         722.31
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.675(3)
_cell_angle_beta                 99.643(3)
_cell_angle_gamma                90.003(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0016(12)
_cell_length_b                   10.9436(19)
_cell_length_c                   17.466(3)
_cell_measurement_reflns_used    3439
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.25
_cell_volume                     1317.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14248
_diffrn_reflns_theta_full        28.87
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.861
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS v2007/5, Sheldrick, G.M., (2007)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             706
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.031
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         8971
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0547
_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^)+(0.1034P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1632
_reflns_number_gt                6373
_reflns_number_total             8971
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c0ob00790k.txt
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C26.50 H16 Br3 F2 N S3'
_cod_database_code               7151749