Site-specific preparation of 3-fluoro-1-substituted-naphthalenes via a novel base-catalyzed cyclization reaction from (E)-monofluoroenynes.
Xu, Jianjun; Wang, Yi; Burton, Donald J.; Organic letters 8 (2006) 2555–2558; doi:10.1021/ol060785z

data_1506006
_publ_section_title
;
 Site-specific preparation of 3-fluoro-1-substituted-naphthalenes via a
 novel base-catalyzed cyclization reaction from (E)-monofluoroenynes.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2555
_journal_page_last               2558
_journal_paper_doi               10.1021/ol060785z
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C20 H26 Cl F'
_chemical_formula_sum            'C20 H26 Cl F'
_chemical_formula_weight         320.86
_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                76.168(10)
_cell_angle_beta                 83.721(10)
_cell_angle_gamma                74.411(10)
_cell_formula_units_Z            4
_cell_length_a                   9.7750(11)
_cell_length_b                   11.6681(17)
_cell_length_c                   16.514(3)
_cell_measurement_reflns_used    3975
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.0
_cell_volume                     1759.6(5)
_computing_cell_refinement       'HKLint Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKLint Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL v5.1 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL v5.1 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL v5.1 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL v5.1 (Sheldrick, 1997)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.882
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0863
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11568
_diffrn_reflns_theta_full        24.92
_diffrn_reflns_theta_max         24.92
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_correction_T_min  0.8729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKLint Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0066P)^2^+0.3186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                3207
_reflns_number_total             5426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060785zsi20060331_041023.cif
_cod_data_source_block           bur14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               1506006