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_4027578
_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_absolute_configuration rm
_chemical_formula_sum            'C20 H27 O5'
_chemical_formula_weight         347.42
_chemical_name_systematic
;
 ?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.032(4)
_cell_length_b                   13.461(6)
_cell_length_c                   16.370(8)
_cell_measurement_reflns_used    496
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      40.77
_cell_measurement_theta_min      4.25
_cell_volume                     1769.9(15)
_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      110(2)
_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  0.2013
_diffrn_reflns_av_sigmaI/netI    0.1470
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13924
_diffrn_reflns_theta_max         59.99
_diffrn_reflns_theta_min         5.40
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.8054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc
 [0.00000+1.00000exp(2.30(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          0.0779
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                1329
_reflns_number_total             2493
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301287z_si_002.cif
_cod_data_source_block           jy02
_cod_original_cell_volume        1769.9(13)
_cod_database_code               4027578