Tandem Reactions via Barton Esters with Intermolecular Addition and Vinyl Radical Substitution onto Indole.
Coyle, Robert; McArdle, Patrick; Aldabbagh, Fawaz; The Journal of organic chemistry 79 (2014) 5903–5907; doi:10.1021/jo5008543

data_4029510
_publ_section_title
;
 Tandem Reactions via Barton Esters with Intermolecular Addition and Vinyl
 Radical Substitution onto Indole.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5903
_journal_page_last               5907
_journal_paper_doi               10.1021/jo5008543
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C22 H18 N2 O2'
_chemical_formula_weight         342.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                66.357(16)
_cell_angle_beta                 76.443(13)
_cell_angle_gamma                63.890(16)
_cell_formula_units_Z            2
_cell_length_a                   9.2424(14)
_cell_length_b                   10.0425(19)
_cell_length_c                   11.6734(18)
_cell_measurement_reflns_used    1141
_cell_measurement_temperature    297.0(1)
_cell_measurement_theta_max      24.9830
_cell_measurement_theta_min      3.7610
_cell_volume                     889.0(3)
_computing_cell_refinement
; 
'Fri Feb 07 01:14:33 2014' 
;
_computing_data_collection
; 
'Fri Feb 07 01:14:33 2014' 
;
_computing_data_reduction
; 
'Fri Feb 07 01:14:33 2014' 
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      297.0(1)
_diffrn_detector_area_resol_mean 16.1048
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5827
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         3.007
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'Fri Feb 07 01:14:33 2014' 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0840
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.1509P)^2^+0.5972P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2505
_refine_ls_wR_factor_ref         0.2810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2118
_reflns_number_total             3247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5008543_si_002.cif
_cod_data_source_block           7b
_cod_depositor_comments
'Adding full bibliography for 4029509--4029510.cif.'
_cod_database_code               4029510
_shelxl_version_number           2013-2
_shelx_res_checksum              57265
_shelx_hkl_checksum              30724