Stereochemical Study of a Transannular Michael Reaction Cascade
Haoran Xue; Peddabuddi Gopal; Jiong Yang; Journal of Organic Chemistry 77 (2012) 8933–8945; doi:10.1021/jo301287z

data_4027579
_publ_section_title
;
 Stereochemical Study of a Transannular Michael Reaction Cascade
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8933
_journal_page_last               8945
_journal_paper_doi               10.1021/jo301287z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C20 H28 O5'
_chemical_formula_weight         348.42
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 114.756(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.689(7)
_cell_length_b                   12.547(7)
_cell_length_c                   11.914(7)
_cell_measurement_reflns_used    193
_cell_measurement_temperature    383(2)
_cell_measurement_theta_max      38.07
_cell_measurement_theta_min      3.84
_cell_volume                     1722.5(17)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      383(2)
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'MWPC area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.4927
_diffrn_reflns_av_sigmaI/netI    0.4275
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12342
_diffrn_reflns_theta_full        59.99
_diffrn_reflns_theta_max         59.99
_diffrn_reflns_theta_min         5.54
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'colorless '
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       'plate     '
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.2899
_refine_ls_R_factor_gt           0.0591
_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
 [0.00000+1.00000exp(2.90(sin\q/\l)^2^)]/
   [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0100P)^2^+0.0000sin\q/\l]
 where P = 0.33333Fo^2^ + 0.66667Fc^2^
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                614
_reflns_number_total             2380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301287z_si_003.cif
_cod_data_source_block           jy05a
_cod_original_cell_volume        1722.5(16)
_cod_database_code               4027579