Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition.
Hayashi, Ryuji; Feltenberger, John B.; Hsung, Richard P.; Organic letters 12 (2010) 1152–1155; doi:10.1021/ol902821w

data_1503412
_publ_section_title
;
 Torquoselective ring closures of chiral amido trienes derived from
 allenamides. A tandem allene isomerization-pericyclic
 ring-closure-intramolecular Diels-Alder cycloaddition.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1152
_journal_page_last               1155
_journal_paper_doi               10.1021/ol902821w
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration adrm
_chemical_formula_moiety         'C27 H30 N2 O4 S'
_chemical_formula_sum            'C27 H30 N2 O4 S'
_chemical_formula_weight         478.59
_chemical_name_common            09166a
_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                   6.3398(7)
_cell_length_b                   10.8464(13)
_cell_length_c                   34.702(4)
_cell_measurement_reflns_used    2706
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.21
_cell_volume                     2386.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
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_diffrn_reflns_limit_h_max       8
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_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21251
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.301
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+1.2305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                4491
_reflns_number_total             5432
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902821w_si_004.cif
_cod_data_source_block           09166a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2386.3(5)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1503412