<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_4033985
_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         'C14 H11 N3 O'
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-02-02
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.705(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.8814(4)
_cell_length_b                   19.4570(4)
_cell_length_c                   11.4871(4)
_cell_measurement_reflns_used    3370
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.8580
_cell_measurement_theta_min      4.1220
_cell_volume                     2392.75(15)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9875
_diffrn_measured_fraction_theta_max 0.9875
_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     61.00 118.00   1.00    1.00    --   25.69 178.00 120.00   57
  2  \w     54.00  80.00   1.00    1.00    --   25.69 -99.00 150.00   26
  3  \w    -12.00  96.00   1.00    1.00    --   25.69  57.00-180.00  108
  4  \w      3.00  30.00   1.00    1.00    --   25.69 -99.00 150.00   27
  5  \w    110.00 150.00   1.00    4.50    --   66.85 111.00  30.00   40
  6  \w    116.00 149.00   1.00    4.50    --   66.85 111.00 -30.00   33
  7  \w    100.00 150.00   1.00    4.50    --   66.85 111.00 -90.00   50
  8  \w     -3.00  85.00   1.00    4.50    --   66.85 -94.00  60.00   88
  9  \w     24.00 138.00   1.00    4.50    --   66.85  77.00 -30.00  114
 10  \w    106.00 147.00   1.00    4.50    --   66.85 111.00-150.00   41
 11  \w     56.00 156.00   1.00   25.00    --  108.00 -89.00-150.00  100
 12  \w    101.00 169.00   1.00   25.00    --  108.00 104.00 150.00   68
 13  \w     38.00 138.00   1.00   25.00    --  108.00 -89.00  60.00  100
 14  \w     38.00 148.00   1.00   25.00    --  108.00 -54.00  60.00  110
 15  \w     71.00 144.00   1.00   25.00    --  108.00 -54.00-180.00   73
 16  \w     32.00  63.00   1.00   25.00    --  108.00 -54.00-180.00   31
 17  \w     27.00 134.00   1.00   25.00    --  108.00 -21.00  30.00  107
;
_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      -0.1410601000
_diffrn_orient_matrix_UB_12      -0.0136774000
_diffrn_orient_matrix_UB_13      -0.0759344000
_diffrn_orient_matrix_UB_21      -0.0281142000
_diffrn_orient_matrix_UB_22      0.0697900000
_diffrn_orient_matrix_UB_23      0.0448493000
_diffrn_orient_matrix_UB_31      0.0013563000
_diffrn_orient_matrix_UB_32      0.0348242000
_diffrn_orient_matrix_UB_33      -0.1199566000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7757
_diffrn_reflns_theta_full        66.83
_diffrn_reflns_theta_max         66.83
_diffrn_reflns_theta_min         4.13
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.538
_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    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             1136.000
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.040
_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     325
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0762P)^2^+0.1999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1335
_reflns_number_gt                3553
_reflns_number_total             4196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b01598_si_004.cif
_cod_data_source_block           sps_3_braz_rt_cu
_cod_original_cell_volume        2392.74(11)
_cod_database_code               4033985
_chemical_oxdiff_formula         'C112 H88 N24 O8 '
_reflns_odcompleteness_completeness 98.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.425
_oxdiff_exptl_absorpt_empirical_full_min 0.829