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_4025853
_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         'C25 H27 N O2'
_chemical_formula_sum            'C25 H27 N O2'
_chemical_formula_weight         373.48
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.843(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.975(3)
_cell_length_b                   16.248(4)
_cell_length_c                   21.172(6)
_cell_measurement_reflns_used    656
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      18.01
_cell_measurement_theta_min      3.86
_cell_volume                     4098.0(18)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.2104
_diffrn_reflns_av_sigmaI/netI    0.1787
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28952
_diffrn_reflns_theta_full        24.11
_diffrn_reflns_theta_max         24.11
_diffrn_reflns_theta_min         3.73
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_correction_T_min  0.9681
_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    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.2093
_refine_ls_R_factor_gt           0.0869
_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^)+(0.0813P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.2255
_reflns_number_gt                2748
_reflns_number_total             6505
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1017734_si_002_3.cif
_cod_data_source_block           a79q
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        4097.9(19)
_cod_database_code               4025853