<i>N</i>-Amino-7-azaindole as the <i>N</i>,<i>N</i>'-Bidentate Directing Group: Ruthenium-Catalyzed Oxidative Annulation of <i>N</i>-(7-Azaindole)benzamides with Alkynes via C-H Bond Activation.
Sagara, Prateep Singh; Siril, Prem Felix; Ravikumar, Ponneri Chandrababu; The Journal of organic chemistry 84 (2019) 12314–12323; doi:10.1021/acs.joc.9b01598

data_4033984
_publ_section_title
;
 <i>N</i>-Amino-7-azaindole as the <i>N</i>,<i>N</i>'-Bidentate Directing
 Group: Ruthenium-Catalyzed Oxidative Annulation of
 <i>N</i>-(7-Azaindole)benzamides with Alkynes via C-H Bond Activation.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12314
_journal_page_last               12323
_journal_paper_doi               10.1021/acs.joc.9b01598
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C24 H19 N3 O'
_chemical_formula_sum            'C24 H19 N3 O'
_chemical_formula_weight         365.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-06-08
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                107.261(5)
_cell_angle_beta                 92.112(4)
_cell_angle_gamma                95.307(5)
_cell_formula_units_Z            4
_cell_length_a                   9.2805(5)
_cell_length_b                   12.3962(7)
_cell_length_c                   16.8806(8)
_cell_measurement_reflns_used    5136
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.2160
_cell_measurement_theta_min      2.1980
_cell_volume                     1842.36(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9870
_diffrn_measured_fraction_theta_max 0.8632
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -12.00  99.00   1.00   23.00    --   26.84  57.00 150.00  111
  2  \w     35.00 120.00   1.00   23.00    --   26.84 178.00  60.00   85
  3  \w    -13.00 104.00   1.00   23.00    --   26.84  77.00-120.00  117
  4  \w    -51.00  24.00   1.00   23.00    --   26.84 -37.00   0.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0718970000
_diffrn_orient_matrix_UB_12      0.0195612000
_diffrn_orient_matrix_UB_13      0.0173247000
_diffrn_orient_matrix_UB_21      0.0187380000
_diffrn_orient_matrix_UB_22      -0.0564773000
_diffrn_orient_matrix_UB_23      -0.0134454000
_diffrn_orient_matrix_UB_31      0.0199716000
_diffrn_orient_matrix_UB_32      0.0077449000
_diffrn_orient_matrix_UB_33      -0.0382634000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11201
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.73
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43i (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             768.000
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0274P)^2^+1.2552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                6306
_reflns_number_total             7946
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b01598_si_002.cif
_cod_data_source_block           sps_44_lt_mo
_cod_original_cell_volume        1842.38(17)
_cod_database_code               4033984
_chemical_oxdiff_formula         'C98 H76 N10 O4 '
_reflns_odcompleteness_completeness 98.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.153
_oxdiff_exptl_absorpt_empirical_full_min 0.880