Regioselective single and double conjugate additions to substituted cyclohexa-2,5-dienone monoacetals.
Grecian, Scott; Wrobleski, Aaron D.; Aubé, Jeffrey; Organic letters 7 (2005) 3167–3170; doi:10.1021/ol050715c

data_1506583
_publ_section_title
;
 Regioselective single and double conjugate additions to substituted
 cyclohexa-2,5-dienone monoacetals.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3167
_journal_page_last               3170
_journal_paper_doi               10.1021/ol050715c
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C23 H29 N O7'
_chemical_formula_sum            'C23 H29 N O7'
_chemical_formula_weight         431.47
_chemical_name_systematic
; 
 Ethyl 9,9-diethoxy-3,7-dioxo-5-
 (phenylcarbamoyl)bicyclo[3.3.1]nonane-2-carboxylate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.088(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5188(12)
_cell_length_b                   14.2466(16)
_cell_length_c                   14.9179(16)
_cell_measurement_reflns_used    8679
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.49
_cell_volume                     2125.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2000)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13141
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        -0.50
_diffrn_standards_number         314
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0500P)^2^+0.8400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                3808
_reflns_number_total             4169
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol050715csi20050404_121828.cif
_cod_data_source_block           compound_17_
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1506583