Asymmetric Organocatalytic Thio-Diels-Alder Reactions via Trienamine Catalysis
Hao Jiang; David Cruz Cruz; Yang Li; Vibeke Henriette Lauridsen; Karl Anker Jørgensen; Journal of the American Chemical Society 135 (2013) 5200–5207; doi:10.1021/ja4007244

data_4119540
_publ_contact_author_name
;
;
_publ_section_title
;
 Asymmetric Organocatalytic Thio-Diels-Alder Reactions via Trienamine
 Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5200
_journal_page_last               5207
_journal_paper_doi               10.1021/ja4007244
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H22 O3 S2'
_chemical_formula_sum            'C14 H22 O3 S2'
_chemical_formula_weight         302.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_date             2012-11-07
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.663(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2144(12)
_cell_length_b                   9.3239(12)
_cell_length_c                   9.5262(13)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    106
_cell_measurement_theta_max      34.06
_cell_measurement_theta_min      2.27
_cell_volume                     770.71(18)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      106
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16358
_diffrn_reflns_theta_full        34.34
_diffrn_reflns_theta_max         34.34
_diffrn_reflns_theta_min         2.27
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.9146
_exptl_absorpt_correction_T_min  0.7547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0820 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.8252.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       irregular
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         5455
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0455P)^2^+0.0765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                5190
_reflns_number_total             5455
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4007244_si_002.cif
_cod_data_source_block           12jo0013a_0m
_cod_database_code               4119540