Stereocontrolled approach to bromofluoroalkenes and their use for the synthesis of tri- and tetrasubstituted fluoroalkenes.
Landelle, Grégory; Champagne, Pier Alexandre; Barbeau, Xavier; Paquin, Jean-François; Organic letters 11 (2009) 681–684; doi:10.1021/ol8027412

data_1503770
_publ_section_title
;
 Stereocontrolled approach to bromofluoroalkenes and their use for the
 synthesis of tri- and tetrasubstituted fluoroalkenes.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              681
_journal_page_last               684
_journal_paper_doi               10.1021/ol8027412
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C12 H14 Br F'
_chemical_formula_sum            'C12 H14 Br F'
_chemical_formula_weight         257.14
_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                 101.653(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.357(3)
_cell_length_b                   19.249(8)
_cell_length_c                   7.358(3)
_cell_measurement_reflns_used    2186
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.63
_cell_measurement_theta_min      2.49
_cell_volume                     1159.2(8)
_computing_cell_refinement       'APEX 2 (Bruker, 2005b)'
_computing_data_collection       'APEX 2 (Bruker, 2005b)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD'
_diffrn_measurement_method       \w
_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  0.0757
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10971
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    3.519
_exptl_absorpt_correction_T_max  0.6977
_exptl_absorpt_correction_T_min  0.4637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     130
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0876P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1659
_reflns_number_gt                1318
_reflns_number_total             2033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8027412_si_002.cif
_cod_data_source_block           jfp0031
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1503770