Direct C-Arylation of Free (NH)-Indoles and Pyrroles Catalyzed by Ar-Rh(III) Complexes Assembled In Situ
Xiang Wang; Benjamin S. Lane; Dalibor Sames; Journal of the American Chemical Society 127 (2005) 4996–4997; doi:10.1021/ja050279p

data_4111623
_publ_section_title
;
 Direct C-Arylation of Free (NH)-Indoles and Pyrroles Catalyzed by
 Ar-Rh(III) Complexes Assembled In Situ
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4996
_journal_page_last               4997
_journal_paper_doi               10.1021/ja050279p
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C59.5 H49.5 Cl1.5 F18 O4 P2 Rh'
_chemical_formula_weight         1388.52
_chemical_name_common            RhP2O2Tol
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.146(2)
_cell_angle_beta                 101.100(2)
_cell_angle_gamma                93.6600(10)
_cell_formula_units_Z            2
_cell_length_a                   12.9032(10)
_cell_length_b                   13.8547(11)
_cell_length_c                   18.2539(13)
_cell_measurement_reflns_used    4607
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      23.22
_cell_measurement_theta_min      2.53
_cell_volume                     3195.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      243(2)
_diffrn_measured_fraction_theta_full 0.877
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.1106
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21704
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  0.8705
_exptl_absorpt_correction_T_min  0.7969
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             1402
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_platon_squeeze_details
;
The unit cell contains one CHCl3 molecule which have been treated as a diffuse

  Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F^2^, conventional R-factors R are based
  on F, with F set to zero for negative F^2^. The threshold expression of
  F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F^2^ are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0000(4)
_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_ref   0.943
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     748
_refine_ls_number_reflns         13916
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.1487
_refine_ls_R_factor_gt           0.0708
_refine_ls_shift/su_max          0.471
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1866
_refine_ls_wR_factor_ref         0.2114
_reflns_number_gt                6383
_reflns_number_total             13916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja050279psi20050124_040737.cif
_cod_data_source_block           rhgzs5ap
_cod_original_formula_sum        'C59.50 H49.50 Cl1.50 F18 O4 P2 Rh'
_cod_database_code               4111623