An Efficient Rh/O2 Catalytic System for Oxidative C-H Activation/Annulation: Evidence for Rh(I) to Rh(III) Oxidation by Molecular Oxygen
Guoying Zhang; Lei Yang; Yanyu Wang; Yinjun Xie; Hanmin Huang; Journal of the American Chemical Society 135 (2013) 8850–8853; doi:10.1021/ja404414q

data_4119956
_publ_contact_author_name
;
;
_publ_section_title
;
 An Efficient Rh/O2 Catalytic System for Oxidative C-H
 Activation/Annulation: Evidence for Rh(I) to Rh(III) Oxidation by
 Molecular Oxygen
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8850
_journal_page_last               8853
_journal_paper_doi               10.1021/ja404414q
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C F3 O3 S, C25 H18 N'
_chemical_formula_sum            'C26 H18 F3 N O3 S'
_chemical_formula_weight         481.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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
_audit_creation_date             2013-05-31
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.272(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.122(2)
_cell_length_b                   9.2388(9)
_cell_length_c                   32.256(4)
_cell_measurement_reflns_used    3387
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.2560
_cell_measurement_theta_min      3.8850
_cell_volume                     4367.4(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9241
_diffrn_measurement_details
;
  1 omega  -87.00  -60.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  178.0000   60.0000 27

  2 omega   -3.00   27.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000   90.0000 30

  3 omega  -48.00   54.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700   77.0000    0.0000 102

  4 omega    2.00   83.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000  120.0000 81

  5 omega    9.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000  -30.0000 84

  6 omega  -15.00   40.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -77.0000  150.0000 55

  7 omega   -3.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000  -90.0000 91

  8 omega  -26.00    1.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -77.0000    0.0000 27

  9 omega   68.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000  120.0000 25

 10 omega  -37.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -38.0000 -180.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0188904000
_diffrn_orient_matrix_UB_12      0.0123505000
_diffrn_orient_matrix_UB_13      -0.0177499000
_diffrn_orient_matrix_UB_21      0.0198163000
_diffrn_orient_matrix_UB_22      -0.0702009000
_diffrn_orient_matrix_UB_23      0.0025806000
_diffrn_orient_matrix_UB_31      -0.0398450000
_diffrn_orient_matrix_UB_32      -0.0288117000
_diffrn_orient_matrix_UB_33      -0.0138805000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            18676
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1984
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0865
_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^)+(0.1051P)^2^+5.7717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2272
_refine_ls_wR_factor_ref         0.2682
_reflns_number_gt                2501
_reflns_number_total             4456
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja404414q_si_003.cif
_cod_data_source_block           huaws0316_1
_cod_original_cell_volume        4367.5(10)
_cod_database_code               4119956
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(S1A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, 
Uanis(F3) \\sim Ueq, Uanis(O1A) \\sim Ueq, Uanis(O2) \\sim Ueq, 
Uanis(O3) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of 0.01 and sigma 
for terminal atoms of 0.02
3. others
 Fixed Sof: S1A(0.5) O1A(0.5) S1B(0.5) O2A(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26)
;