A simple base-mediated synthesis of diverse functionalized ring-fluorinated 4H-pyrans via double direct C-F substitutions
Jieru Yang; Ao Mao; Zhenting Yue; Wenxuan Zhu; Xuewei Luo; Chuwei Zhu; Yuanjing Xiao; Junliang Zhang; Chem.Commun. 51 (2015) 8326–; doi:10.1039/C5cc02073E

data_7117131
_publ_section_title
;
 A simple base-mediated synthesis of diverse functionalized
 ring-fluorinated 4H-pyrans via double direct C-F substitutions
;
_journal_name_full               Chem.Commun.
_journal_page_first              8326
_journal_paper_doi               10.1039/C5cc02073E
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C16 H13 F O2'
_chemical_formula_weight         256.26
_chemical_name_systematic
1-(6-fluoro-2-methyl-5-(phenylethynyl)-4H-pyran-3-yl)ethanone
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-10 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.1810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.8977(9)
_cell_length_b                   8.7711(3)
_cell_length_c                   11.9279(4)
_cell_measurement_temperature    173(2)
_cell_volume                     2526.40(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14325
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hexane'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0450P)^2^+1.8099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                1924
_reflns_number_total             2229
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02073e2.cif
_cod_data_source_block           z_1
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7117131