Organocatalytic diastereoselective synthesis of chiral decalines through the domino Claisen-Schmidt/Henry reaction.
Shashank, Adluri B.; Ramachary, Dhevalapally B.; Organic & biomolecular chemistry 13 (2015) 5110–5114; doi:10.1039/c5ob00562k

data_7154393
_publ_section_title
;
 Organocatalytic diastereoselective synthesis of chiral decalines through
 the domino Claisen-Schmidt/Henry reaction.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5110
_journal_page_last               5114
_journal_paper_doi               10.1039/c5ob00562k
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_sum            'C20 H27 N O5'
_chemical_formula_weight         361.43
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-12 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.099(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9810(4)
_cell_length_b                   11.3115(5)
_cell_length_c                   9.4917(7)
_cell_measurement_reflns_used    4203
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8252
_cell_measurement_theta_min      3.9072
_cell_volume                     893.41(10)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4718
_diffrn_reflns_theta_full        72.99
_diffrn_reflns_theta_max         72.99
_diffrn_reflns_theta_min         5.32
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  0.8218
_exptl_absorpt_correction_T_min  0.7338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0654P)^2^+0.1774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                2769
_reflns_number_total             2805
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00562k4.cif
_cod_data_source_block           dbr30
_cod_depositor_comments
'Adding full bibliography for 7154392--7154393.cif.'
_cod_original_cell_volume        893.41(9)
_cod_database_code               7154393