Enantiospecific Photochemical Norrish/Yang Type II Reaction of Nonbiaryl Atropchiral α-Oxoamides in Solution-Axial to Point Chirality Transfer
Anoklase Jean-Luc Ayitou; Josepha L. Jesuraj; Nilotpal Barooah; Angel Ugrinov; J. Sivaguru; Journal of the American Chemical Society 131 (2009) 11314–11315; doi:10.1021/ja9050586

data_4104880
_publ_contact_author
;
J. Sivaguru
Dunbar Hall
Department of Chemistry
North Dakota State University
Fargo, ND 58105
USA
;
_publ_contact_author_email       sivaguru.jayaraman@ndsu.edu
_publ_contact_author_fax         'Intl. Code + (701)231-8831'
_publ_contact_author_phone       'Intl. Code + (701)231-8923'
_publ_section_title
;
 Enantiospecific Photochemical Norrish/Yang Type II Reaction of Nonbiaryl
 Atropchiral \a-Oxoamides in Solution-Axial to Point Chirality Transfer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11314
_journal_page_last               11315
_journal_paper_doi               10.1021/ja9050586
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C23 H29 N O2'
_chemical_formula_weight         351.47
_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                 92.290(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6015(16)
_cell_length_b                   12.896(2)
_cell_length_c                   16.782(3)
_cell_measurement_reflns_used    924
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.40
_cell_volume                     2076.3(6)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13476
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.711859
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       Lump
_exptl_crystal_F_000             760
_exptl_crystal_size_max          .80
_exptl_crystal_size_mid          .56
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0946P)^2^+0.2692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1817
_reflns_number_gt                3419
_reflns_number_total             4979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9050586_si_002_1.cif
_cod_data_source_block           1a
_cod_original_cell_volume        2076.4(6)
_cod_database_code               4104880