Rhodium(II)-Catalyzed Intramolecular Annulation of 1-Sulfonyl-1,2,3-Triazoles with Indoles: Facile Synthesis of Functionalized Tetrahydro-β-Carbolines
Shang, Hai; Tian, Yu; Luo, Jun; Li, Ling-Yu; Tang, Yefeng; Zou, Zhong-Mei; RSC Adv.  (2016) –; doi:10.1039/C6RA02923J

data_7224642
_publ_section_title
;
 Rhodium(II)-Catalyzed Intramolecular Annulation of
 1-Sulfonyl-1,2,3-Triazoles with Indoles: Facile Synthesis of
 Functionalized Tetrahydro-\b-Carbolines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA02923J
_journal_year                    2016
_chemical_formula_moiety         'C27 H29 N3 O4 S2, C H2 Cl2'
_chemical_formula_sum            'C28 H31 Cl2 N3 O4 S2'
_chemical_formula_weight         608.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2015-10-30
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2016-01-21 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                71.536(4)
_cell_angle_beta                 83.542(4)
_cell_angle_gamma                81.195(4)
_cell_formula_units_Z            2
_cell_length_a                   9.7402(4)
_cell_length_b                   11.9977(7)
_cell_length_c                   13.1123(5)
_cell_measurement_reflns_used    3868
_cell_measurement_temperature    106.6
_cell_measurement_theta_max      29.4781
_cell_measurement_theta_min      3.1674
_cell_volume                     1432.94(12)
_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      106.6
_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  -46.00  -11.00   1.0000    2.2600
omega____ theta____ kappa____ phi______ frames
    -       18.8897  -77.0000  120.0000 35

  2 omega  -30.00   37.00   1.0000    2.2600
omega____ theta____ kappa____ phi______ frames
    -       18.8897  -37.0000  -30.0000 67

  3 omega   -4.00   28.00   1.0000    2.2600
omega____ theta____ kappa____ phi______ frames
    -       18.8897   77.0000    0.0000 32

  4 omega    4.00   46.00   1.0000    2.2600
omega____ theta____ kappa____ phi______ frames
    -       18.8897   67.0000   89.0000 42

  5 omega  -40.00   38.00   1.0000    2.2600
omega____ theta____ kappa____ phi______ frames
    -       18.8897  -67.0000  136.0000 78

  6 omega   -8.00   86.00   1.0000    2.2600
omega____ theta____ kappa____ phi______ frames
    -       18.8897   77.0000 -120.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0480116000
_diffrn_orient_matrix_UB_12      -0.0137892000
_diffrn_orient_matrix_UB_13      -0.0404236000
_diffrn_orient_matrix_UB_21      0.0176100000
_diffrn_orient_matrix_UB_22      0.0586424000
_diffrn_orient_matrix_UB_23      -0.0170560000
_diffrn_orient_matrix_UB_31      0.0532957000
_diffrn_orient_matrix_UB_32      -0.0178042000
_diffrn_orient_matrix_UB_33      0.0366425000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9944
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91191
_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    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0302P)^2^+0.8549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                4708
_reflns_number_total             5606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra02923j2.cif
_cod_data_source_block           exp_3565
_cod_original_cell_volume        1432.95(12)
_cod_database_code               7224642
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32