How do analogous alpha-chloroenamides and alpha-iodoenamides give different product distributions in 5-endo radical cyclizations?
Curran, Dennis P.; Guthrie, David B.; Geib, Steven J.; Journal of the American Chemical Society 130 (2008) 8437–8445; doi:10.1021/ja8012962

data_4121938
_publ_section_title
;
 How do analogous alpha-chloroenamides and alpha-iodoenamides give
 different product distributions in 5-endo radical cyclizations?
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8437
_journal_page_last               8445
_journal_paper_doi               10.1021/ja8012962
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C15 H18 Cl N O'
_chemical_formula_sum            'C15 H18 Cl N O'
_chemical_formula_weight         263.75
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.263(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.852(5)
_cell_length_b                   9.106(5)
_cell_length_c                   9.389(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_cell_volume                     695.3(7)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6450
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.50
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker AXS Smart Apex CDD'
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.8820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.331
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_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1434 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0820P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                2471
_reflns_number_total             3132
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            dguth1.cif
_cod_data_source_block           dguth1
_cod_original_cell_volume        695.2(6)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4121938