Asymmetry by electrophilic rearrangement of symmetric 2-pyridone photodimers.
Lim, Yeon-Hee; Li, Tindy; Chen, Peiling; Schreiber, Patrick; Kuznetsova, Larissa; Carroll, Patrick J.; Lauher, Joseph W.; Sieburth, Scott McN; Organic letters 7 (2005) 5413–5415; doi:10.1021/ol052071e

data_1506741
_publ_section_title
;
 Asymmetry by electrophilic rearrangement of symmetric 2-pyridone
 photodimers.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5413
_journal_page_last               5415
_journal_paper_doi               10.1021/ol052071e
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C18 H26 Cl2 N2 O2'
_chemical_formula_weight         373.3
_space_group_IT_number           29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 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                   14.174(2)
_cell_length_b                   11.5857(17)
_cell_length_c                   12.0325(18)
_cell_measurement_temperature    293(2)
_cell_volume                     1975.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0811
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10987
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.25
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.770
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.076
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0888P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1569
_reflns_number_gt                1628
_reflns_number_total             4034
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052071esi20050827_120243.cif
_cod_data_source_block           d:\lauher\jlb\work\jlb
_cod_original_sg_symbol_H-M      Pca21
_cod_database_code               1506741