Synthesis of γ-Monofluorinated Goniothalamin Analogues via Regio- and Stereoselective Ring-Opening Hydrofluorination of Epoxide
Jun-Ling Chen; Feng Zheng; Yangen Huang; Feng-Ling Qing; Journal of Organic Chemistry 76 (2011) 6525–6533; doi:10.1021/jo200611w

data_4026502
_publ_section_title
;
 Synthesis of \g-Monofluorinated Goniothalamin Analogues via Regio- and
 Stereoselective Ring-Opening Hydrofluorination of Epoxide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6525
_journal_page_last               6533
_journal_paper_doi               10.1021/jo200611w
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H11 F O2'
_chemical_formula_weight         218.22
_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                 95.498(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.356(2)
_cell_length_b                   5.4364(13)
_cell_length_c                   23.154(5)
_cell_measurement_reflns_used    7121
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.45
_cell_volume                     1047.0(4)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6568
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9615
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0571P)^2^+0.4660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                3777
_reflns_number_total             3959
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200611w_si_001.cif
_cod_data_source_block           mo_dm10115_0m
_cod_original_cell_volume        1046.9(4)
_cod_database_code               4026502