Synthesis of 4-Aryl- and 4-Alkyl-2-silyl-1,3-butadienes and Their Diels-Alder/Cross-Coupling Reactions
Christopher S. Junker; Mark E. Welker; Cynthia S. Day; Journal of Organic Chemistry 75 (2010) 8155–8165; doi:10.1021/jo1017734

data_4025852
_publ_contact_author_address
; 
Department of Chemistry 
Wake Forest University
P. O. Box 7486
Winston-Salem, N.C. 27109
U.S.A.
;
_publ_contact_author_email       welker@wfu.edu
_publ_contact_author_fax         '336 758 4656'
_publ_contact_author_name        'Mark E. Welker'
_publ_contact_author_phone       '336 758 5758'
_publ_section_title
;
 Synthesis of 4-Aryl- and 4-Alkyl-2-silyl-1,3-butadienes and Their
 Diels-Alder/Cross-Coupling Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8155
_journal_page_last               8165
_journal_paper_doi               10.1021/jo1017734
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C24 H26 O3 Si'
_chemical_formula_sum            'C24 H26 O3 Si'
_chemical_formula_weight         390.54
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1897(9)
_cell_length_b                   10.0648(12)
_cell_length_c                   29.034(4)
_cell_measurement_reflns_used    3944
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      3.99
_cell_volume                     2101.0(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19570
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.99
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for scaling and absorption effects
 using the  multi-scan technique (SADABS) Sheldrick, G. M. (2008).  
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2035 Friedel pairs'
_refine_ls_abs_structure_Flack   0.22(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.2776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1298
_reflns_number_gt                4271
_reflns_number_total             4786
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1017734_si_002_2.cif
_cod_data_source_block           a82q2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2101.0(4)
_cod_database_code               4025852