Activating Pyrimidines by Pre-distortion for the General Synthesis of 7-Aza-indazoles from 2-Hydrazonylpyrimidines via Intramolecular Diels-Alder Reactions.
Le Fouler, Vincent; Chen, Yu; Gandon, Vincent; Bizet, Vincent; Salomé, Christophe; Fessard, Thomas; Liu, Fang; Houk, K. N.; Blanchard, Nicolas; Journal of the American Chemical Society 141 (2019) 15901–15909; doi:10.1021/jacs.9b07037

data_4128356
_publ_section_title
;
 Activating Pyrimidines by Pre-distortion for the General Synthesis of
 7-Aza-indazoles from 2-Hydrazonylpyrimidines via Intramolecular
 Diels-Alder Reactions.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15901
_journal_page_last               15909
_journal_paper_doi               10.1021/jacs.9b07037
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C14 H11 F N4'
_chemical_formula_sum            'C14 H11 F N4'
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-15 deposited with the CCDC.    2019-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_length_c                   9.4452(3)
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_cell_measurement_temperature    173(2)
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_cell_measurement_theta_min      0.998
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_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_theta_min         1.733
_diffrn_source                   'sealed tube'
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_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.448
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.1006
_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^)+(0.0647P)^2^+1.1749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2446
_reflns_number_total             2805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07037_si_004.cif
_cod_data_source_block           flvlf180702
_cod_database_code               4128356
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              10986
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