Chelation-assisted Rh(iii)-catalyzed C2-selective oxidative C–H/C–H cross-coupling of indoles/pyrroles with heteroarenes
Qin, Xurong; Liu, Hu; Qin, Dekun; Wu, Qian; You, Jingsong; Zhao, Dongbing; Guo, Qiang; Huang, Xiaolei; Lan, Jingbo; Chemical Science 4 (2013) 1964–; doi:10.1039/c3sc22241a

data_1514675
_publ_section_title
;
 Chelation-assisted Rh(iii)-catalyzed C2-selective oxidative C--H/C--H
 cross-coupling of indoles/pyrroles with heteroarenes
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              1964
_journal_paper_doi               10.1039/c3sc22241a
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C20 H13 N3 S'
_chemical_formula_sum            'C20 H13 N3 S'
_chemical_formula_weight         327.39
_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             2012-06-18
_audit_creation_method
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                76.211(6)
_cell_angle_beta                 79.041(6)
_cell_angle_gamma                87.821(6)
_cell_formula_units_Z            2
_cell_length_a                   8.3008(6)
_cell_length_b                   10.0109(8)
_cell_length_c                   10.1613(6)
_cell_measurement_reflns_used    1962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9300
_cell_measurement_theta_min      2.9442
_cell_volume                     805.07(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1 omega -25.00 1.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -99.0000 -30.0000 26
2 omega -21.00 22.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -99.0000 30.0000 43
3 omega -14.00 15.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -99.0000 -180.0000 29
4 omega -90.00 -45.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -178.0000 -180.0000 45
5 omega -5.00 83.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 37.0000 -120.0000 88
6 omega 38.00 82.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 178.0000 90.0000 44
7 omega -53.00 46.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 -37.0000 60.0000 99
8 omega -49.00 6.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 -57.0000 -180.0000 55
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0767354000
_diffrn_orient_matrix_UB_12      0.0340801000
_diffrn_orient_matrix_UB_13      -0.0126743000
_diffrn_orient_matrix_UB_21      0.0410771000
_diffrn_orient_matrix_UB_22      -0.0623405000
_diffrn_orient_matrix_UB_23      -0.0058627000
_diffrn_orient_matrix_UB_31      -0.0003555000
_diffrn_orient_matrix_UB_32      0.0165843000
_diffrn_orient_matrix_UB_33      -0.0718150000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6779
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0405P)^2^+0.2036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2225
_reflns_number_total             3297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc22241a.txt
_cod_data_source_block           120618_s4_qxr
_cod_database_code               1514675
_chemical_oxdiff_formula         C12H15N3S1
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32