Controlled Ring-Opening of Siloxydifluorocyclopropanes for Carbocyclization: Synthesis of Difluorocyclopentenones.
Song, Xiaoning; Tian, Shuangquan; Zhao, Ziming; Zhu, Dongsheng; Wang, Mang; Organic letters 18 (2016) 3414–3417; doi:10.1021/acs.orglett.6b01567

data_1543598
_publ_section_title
;
 Controlled Ring-Opening of Siloxydifluorocyclopropanes for
 Carbocyclization: Synthesis of Difluorocyclopentenones.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3414
_journal_page_last               3417
_journal_paper_doi               10.1021/acs.orglett.6b01567
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C13 H11 F3 O S'
_chemical_formula_sum            'C13 H11 F3 O S'
_chemical_formula_weight         272.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.167(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9390(10)
_cell_length_b                   8.2520(8)
_cell_length_c                   11.8780(8)
_cell_measurement_reflns_used    1922
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1869
_cell_measurement_theta_min      2.9415
_cell_volume                     1239.76(18)
_computing_cell_refinement
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_data_collection
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_data_reduction
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4384
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_correction_T_min  0.9405
_exptl_absorpt_process_details
;
CrysAlis (Oxford Diffraction, 2006)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0596P)^2^+0.2534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                1771
_reflns_number_total             2257
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol6b01567_si_002.cif
_cod_data_source_block           compound4a
_cod_depositor_comments          'Adding full bibliography for 1543598.cif.'
_cod_original_cell_volume        1239.76(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1543598