Ruthenium-Catalyzed Direct and Selective C-H Cyanation of N-(Hetero)aryl-7-azaindoles.
Mishra, Aniket; Vats, Tripta Kumari; Deb, Indubhusan; The Journal of organic chemistry 81 (2016) 6525–6534; doi:10.1021/acs.joc.6b01148

data_4036988
_publ_section_title
;
 Ruthenium-Catalyzed Direct and Selective C-H Cyanation of
 N-(Hetero)aryl-7-azaindoles.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6525
_journal_page_last               6534
_journal_paper_doi               10.1021/acs.joc.6b01148
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C18 H11 N3'
_chemical_formula_sum            'C18 H11 N3'
_chemical_formula_weight         269.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9453(19)
_cell_length_b                   6.9618(7)
_cell_length_c                   20.894(3)
_cell_measurement_reflns_used    1384
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.502
_cell_measurement_theta_min      2.902
_cell_volume                     2755.8(6)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1136
_diffrn_reflns_av_unetI/netI     0.1087
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24093
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.734
_diffrn_reflns_theta_min         2.903
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1093 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.8116.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0093(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.1657
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1993
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1350
_reflns_number_total             3173
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01148_si_002.cif
_cod_data_source_block           ibd_am05_40_0m
_cod_original_cell_volume        2755.7(5)
_cod_database_code               4036988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16)
;
_shelx_res_checksum              56685
_shelx_hkl_checksum              61336
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'