Synthesis of Heteroannulated Indolopyrazines through Domino N‒H Palladium-Catalyzed/Metal-Free Oxidative C‒H Bond Activation
Kvashnin, Yuriy A.; Verbitskiy, Egor V.; Zhilina, Ekaterina F.; Rusinov, Gennady L.; Chupakhin, Oleg N.; Charushin, Valery N.; ACS Omega 5 (2020) 15681–15690; doi:10.1021/acsomega.0c01945

data_4517787
_publ_section_title
;
 Synthesis of Heteroannulated Indolopyrazines through Domino N--H
 Palladium-Catalyzed/Metal-Free Oxidative C--H Bond Activation
;
_journal_issue                   25
_journal_name_full               'ACS Omega'
_journal_page_first              15681
_journal_page_last               15690
_journal_paper_doi               10.1021/acsomega.0c01945
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C17 H11 N5 O'
_chemical_formula_sum            'C17 H11 N5 O'
_chemical_formula_weight         301.31
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.939(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0497(11)
_cell_length_b                   8.9240(9)
_cell_length_c                   22.361(3)
_cell_measurement_reflns_used    1568
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.7630
_cell_measurement_theta_min      3.6760
_cell_volume                     1403.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11020
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.77
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0037(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0540P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                1885
_reflns_number_total             3788
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao0c01945_si_001.cif
_cod_data_source_block           exp_229
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4517787.cif.

 Adding full bibliography for 4517787.cif.
;
_cod_original_cell_volume        1403.5(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4517787