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_4027580
_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            'C19 H26 O4'
_chemical_formula_weight         318.40
_space_group_IT_number           2
_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                88.659(9)
_cell_angle_beta                 86.896(9)
_cell_angle_gamma                70.776(9)
_cell_formula_units_Z            2
_cell_length_a                   7.1136(9)
_cell_length_b                   10.6900(13)
_cell_length_c                   12.6430(16)
_cell_measurement_reflns_used    1010
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      58.17
_cell_measurement_theta_min      3.50
_cell_volume                     906.5(2)
_computing_cell_refinement
; 
  CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) 
;
_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    Olex2
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'phi and omega 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  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20832
_diffrn_reflns_theta_full        59.97
_diffrn_reflns_theta_max         59.97
_diffrn_reflns_theta_min         5.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_platon_squeeze_details
;
Ethyl acetate was used for crystallization. 
Solvent atoms were found in the structure
which could not be identified clearly due
to partial occupancy and disorder. The solvent
was SQUEEZED out using PLATON. The number of
electrons, 43 in the unit cell, and 10.7 electrons
per asymmetric unit accounts for a water molecule 
disordered in several positions.
;
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0118(12)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0406
_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(1.00(sin\q/\l)^2^)]/ 
   [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0654P)^2^+0.0000sin\q/\l] 
 where P = 0.33333Fo^2^ + 0.66667Fc^2^ 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                1904
_reflns_number_total             2612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301287z_si_004.cif
_cod_data_source_block           jyb
_cod_database_code               4027580