Enantioselective C–H Annulation of Indoles with Diazo Compounds through a Chiral Rh(III) Catalyst
Chen, Xiaohong; Yang, Shujing; Li, Helong; Wang, Bo; Song, Guoyong; ACS Catalysis  (2017) 2392–; doi:10.1021/acscatal.7b00104

data_4514048
_publ_section_title
;
 Enantioselective C--H Annulation of Indoles with Diazo Compounds through
 a Chiral Rh(III) Catalyst
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2392
_journal_paper_doi               10.1021/acscatal.7b00104
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H26 N2 O5'
_chemical_formula_sum            'C21 H26 N2 O5'
_chemical_formula_weight         386.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-10
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 121.047(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.5768(11)
_cell_length_b                   8.5784(2)
_cell_length_c                   12.0175(6)
_cell_measurement_reflns_used    4232
_cell_measurement_temperature    105.1
_cell_measurement_theta_max      70.8736
_cell_measurement_theta_min      4.2897
_cell_volume                     1994.04(19)
_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      105.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -64.00  -28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  137.0000   78.0000 36

  2 omega   50.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   37.0000  -30.0000 53

  3 omega   11.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   76.0000 -160.0000 90

  4 omega   72.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   37.0000    0.0000 30

  5 omega   31.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036 -137.0000  101.0000 26

  6 omega  -30.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -77.0000    0.0000 92

  7 omega   26.00   52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   37.0000   90.0000 26

  8 omega   59.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   37.0000   90.0000 26

  9 omega  -33.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -77.0000   90.0000 95

 10 omega   54.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8036 -137.0000   15.0000 31

 11 omega   91.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 76

 12 omega   73.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 50

 13 omega   71.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 33

 14 omega   83.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 44

 15 omega   40.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 53

 16 omega  142.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 30

 17 omega  104.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 74

 18 omega   84.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   76.0000  -73.0000 32

 19 omega   90.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -132.0000 -167.0000 25

 20 omega   94.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 82

 21 omega   72.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 65

 22 omega   91.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 80

 23 omega   40.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -132.0000 -167.0000 28

 24 omega   60.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 26

 25 omega  134.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 35

 26 omega   84.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 87

 27 omega  111.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 58

 28 omega  126.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0537469000
_diffrn_orient_matrix_UB_12      -0.1094735000
_diffrn_orient_matrix_UB_13      0.0012258000
_diffrn_orient_matrix_UB_21      -0.0587730000
_diffrn_orient_matrix_UB_22      0.1026772000
_diffrn_orient_matrix_UB_23      -0.1028579000
_diffrn_orient_matrix_UB_31      -0.0015421000
_diffrn_orient_matrix_UB_32      -0.0983753000
_diffrn_orient_matrix_UB_33      -0.1086025000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6755
_diffrn_reflns_theta_full        71.08
_diffrn_reflns_theta_max         71.08
_diffrn_reflns_theta_min         4.29
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92319
_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_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3774
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.3815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                3686
_reflns_number_total             3774
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs7b00104_si_002.cif
_cod_data_source_block           exp_4532
_cod_original_cell_volume        1994.03(14)
_cod_database_code               4514048
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97