Carbene-Catalyzed Indole 3-Methyl C(sp3)-H Bond Functionalization.
Cheng, Jian; Sun, Jun; Yan, Jiekuan; Yang, Song; Zheng, Pengcheng; Jin, Zhichao; Chi, Yonggui Robin; The Journal of organic chemistry 82 (2017) 13342–13347; doi:10.1021/acs.joc.7b02436

data_4033198
_publ_section_title
;
 Carbene-Catalyzed Indole 3-Methyl C(sp3)-H Bond Functionalization.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13342
_journal_page_last               13347
_journal_paper_doi               10.1021/acs.joc.7b02436
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C23 H20 F3 N O4, C3 H6'
_chemical_formula_sum            'C26 H26 F3 N O4'
_chemical_formula_weight         473.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-03-06
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.486(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1234(8)
_cell_length_b                   10.6110(12)
_cell_length_c                   15.8504(12)
_cell_measurement_reflns_used    3314
_cell_measurement_temperature    100.3
_cell_measurement_theta_max      29.2695
_cell_measurement_theta_min      3.2772
_cell_volume                     2289.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      100.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -5.00   54.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0609   37.0000  -90.0000 59

  2 omega  -60.00  -11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0609  115.0000 -100.0000 49

  3 omega    8.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2171   37.0000  150.0000 84

  4 omega   16.00   51.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2171  -77.0000    0.0000 35

  5 omega  -21.00    5.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2171  -77.0000    0.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0259717000
_diffrn_orient_matrix_UB_12      0.0540714000
_diffrn_orient_matrix_UB_13      0.0075905000
_diffrn_orient_matrix_UB_21      -0.0421244000
_diffrn_orient_matrix_UB_22      -0.0375608000
_diffrn_orient_matrix_UB_23      -0.0023768000
_diffrn_orient_matrix_UB_31      0.0162751000
_diffrn_orient_matrix_UB_32      -0.0108310000
_diffrn_orient_matrix_UB_33      0.0457435000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9850
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0478P)^2^+1.8132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                3715
_reflns_number_total             4492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02436_si_002.cif
_cod_data_source_block           exp_4801
_cod_depositor_comments          'Adding full bibliography for 4033198.cif.'
_cod_database_code               4033198
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32