Thermal C1-C5 Diradical Cyclization of Enediynes
Chandrasekhar Vavilala; Neal Byrne; Christina M. Kraml; Douglas M. Ho; Robert A. Pascal; Journal of the American Chemical Society 130 (2008) 13549–13551; doi:10.1021/ja803413f

data_4108459
_publ_section_title
;
 Thermal C1-C5 Diradical Cyclization of Enediynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13549
_journal_page_last               13551
_journal_paper_doi               10.1021/ja803413f
_journal_volume                  130
_journal_year                    2008
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C22 H12 Cl6'
_chemical_formula_moiety         'C22 H12 Cl6'
_chemical_formula_structural     'C22 H12 Cl6'
_chemical_formula_sum            'C22 H12 Cl6'
_chemical_formula_weight         489.02
_chemical_name_systematic
; 
 2-(2,4,6-trichlorophenyl)-3-[(2,4,6-trichlorophenyl)methyl]indene 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.552(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3411(4)
_cell_length_b                   16.6406(5)
_cell_length_c                   9.3406(3)
_cell_measurement_reflns_used    4854
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.63
_cell_measurement_theta_min      2.45
_cell_volume                     2024.09(11)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction
;
 SAINT V7.34A (Bruker AXS, 2006b), SADABS (Bruker AXS, 2004)
;
_computing_molecular_graphics    'Siemens SHELXTL (Sheldrick, 1996)'
_computing_publication_material  'Siemens SHELXTL (Sheldrick, 1996)'
_computing_structure_refinement  'Siemens SHELXTL (Sheldrick, 1996)'
_computing_structure_solution    'Siemens SHELXTL (Sheldrick, 1996)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 1600 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14144
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  0.8647
_exptl_absorpt_correction_T_min  0.7398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       Needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0014(3)
_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_all   1.068
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.069
_refine_ls_restrained_S_obs      1.123
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0253P)^2^+2.2330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1094
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                1905
_reflns_number_total             2330
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja803413f_si_003.cif
_cod_data_source_block           rap08002mf
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4108459