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_1504038
_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_sum            'C8 H6 Cl I'
_chemical_formula_weight         264.48
_chemical_name_systematic
;
1-chloro-4-[(E)-2-iodoethenyl]benzene
;
_space_group_IT_number           1
_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                91.31(3)
_cell_angle_beta                 91.52(3)
_cell_angle_gamma                99.58(3)
_cell_formula_units_Z            4
_cell_length_a                   7.3520(15)
_cell_length_b                   7.3650(15)
_cell_length_c                   16.241(3)
_cell_measurement_reflns_used    3256
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      4
_cell_volume                     866.5(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.884
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7496
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.80
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    3.926
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_correction_T_min  0.287
_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    2.027
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       0.0061(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4703
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0837P)^2^+0.1666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                3487
_reflns_number_total             4703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901233j_si_001.cif
_cod_data_source_block           1
_cod_database_code               1504038