New one-pot synthesis of (E)-beta-aryl vinyl halides from styrenes.
Pawluć, Piotr; Hreczycho, Grzegorz; Szudkowska, Justyna; Kubicki, Maciej; Marciniec, Bogdan; Organic letters 11 (2009) 3390–3393; doi:10.1021/ol901233j

data_1504039
_publ_contact_author
;
Maciej Kubicki   
Faculty of Chemistry 
Adam Mickiewicz University
Grunwaldzka 6              
60-780 Pozna\'n   
Poland             
;
_publ_section_title
;
 New one-pot synthesis of (E)-beta-aryl vinyl halides from styrenes.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3390
_journal_page_last               3393
_journal_paper_doi               10.1021/ol901233j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C8 H6 Br I'
_chemical_formula_sum            'C8 H6 Br I'
_chemical_formula_weight         308.93
_chemical_name_systematic
;
1-bromo-4-[(E)-2-iodoethenyl]benzene
;
_space_group_IT_number           27
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 -2c'
_symmetry_space_group_name_H-M   'P c c 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2421(2)
_cell_length_b                   20.3220(7)
_cell_length_c                   5.8538(2)
_cell_measurement_reflns_used    2747
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      24
_cell_measurement_theta_min      3
_cell_volume                     861.53(5)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction (2007))'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction (2007))'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction (2007))'
_computing_molecular_graphics
;
XP (Siemens, 1989), Mercury (Macrae et al, 2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'KUMA KM4CCD diffractometer'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10292
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.96
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    8.276
_exptl_absorpt_correction_T_max  0.437
_exptl_absorpt_correction_T_min  0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.786
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.202
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.198(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1924
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0612P)^2^+0.7608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0903
_reflns_number_gt                1795
_reflns_number_total             1924
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901233j_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      Pcc2
_cod_database_code               1504039