Mechanistic Studies on the Heck-Mizoroki Cross-Coupling Reaction of a Hindered Vinylboronate Ester as a Key Approach to Developing a Highly Stereoselective Synthesis of a C1-C7 Z,Z,E-Triene Synthon for Viridenomycin
Andrei S. Batsanov; Jonathan P. Knowles; Andrew Whiting; Journal of Organic Chemistry 72 (2007) 2525–2532; doi:10.1021/jo0626010

data_4022836
_publ_contact_author             'Andrei S.Batsanov'
_publ_contact_author_email       a.s.batsanov@durham.ac.uk
_publ_section_title
;
 Mechanistic Studies on the Heck-Mizoroki Cross-Coupling Reaction
 of a Hindered Vinylboronate Ester as a Key Approach to
 Developing a Highly Stereoselective Synthesis of a
 C1-C7 Z,Z,E-Triene Synthon for Viridenomycin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2525
_journal_page_last               2532
_journal_paper_doi               10.1021/jo0626010
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C3 H4 I2 O2'
_chemical_formula_sum            'C3 H4 I2 O2'
_chemical_formula_weight         325.86
_chemical_melting_point          358.8(6)
_chemical_name_systematic
; 
 3,3-diiodopropionic acid  
;
_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
_audit_update_record
;
2006-12-18 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.61(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7244(17)
_cell_length_b                   6.5787(9)
_cell_length_c                   8.8078(12)
_cell_measurement_reflns_used    6346
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      28.99
_cell_measurement_theta_min      2.37
_cell_volume                     719.52(17)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.054 (Bruker, 1999)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area detector'
_diffrn_measurement_method       '\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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8140
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         1.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.651
_exptl_absorpt_correction_T_max  0.6394
_exptl_absorpt_correction_T_min  0.3387
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'XPREP v.6.12 (Bruker,2001), R(int)=0.080 before correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    3.008
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.427
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0181
_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^)+(0.0205P)^2^+0.6702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0442
_refine_ls_wR_factor_ref         0.0451
_reflns_number_gt                1739
_reflns_number_total             1898
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo0626010si20070126_093550.cif
_cod_data_source_block           05srv333
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022836