Light-Induced Enantiospecific 4π Ring Closure of Axially Chiral 2-Pyridones: Enthalpic and Entropic Effects Promoted by H-Bonding
Elango Kumarasamy; Josepha L. Jesuraj; Joseph N. Omlid; Angel Ugrinov; Jayaraman Sivaguru; Journal of the American Chemical Society 133 (2011) 17106–17109; doi:10.1021/ja203087a

data_4107016
_publ_contact_author_name        'Jayaraman Sivaguru'
_publ_contact_author_phone       '701 231-8923'
_publ_section_title
;
 Light-Induced Enantiospecific 4\p Ring Closure of Axially Chiral
 2-Pyridones: Enthalpic and Entropic Effects Promoted by H-Bonding
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17106
_journal_page_last               17109
_journal_paper_doi               10.1021/ja203087a
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H17 N O'
_chemical_formula_sum            'C15 H17 N O'
_chemical_formula_weight         227.30
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_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            8
_cell_length_a                   6.8746(2)
_cell_length_b                   12.4881(4)
_cell_length_c                   30.4034(9)
_cell_measurement_reflns_used    9823
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.14
_cell_measurement_theta_min      2.91
_cell_volume                     2610.15(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            25477
_diffrn_reflns_theta_full        66.56
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  0.9606
_exptl_absorpt_correction_T_min  0.8862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Acta Cryst (1995). A51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       rod
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(16)
_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     313
_refine_ls_number_reflns         4435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0261
_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^)+(0.0383P)^2^+0.4633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                4390
_reflns_number_total             4435
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203087a_si_002_4.cif
_cod_data_source_block           P_1a_in_P2(1)2(1)2(1)
_cod_database_code               4107016