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_4128355
_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         'C13 H10 F N3'
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_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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
;
2019-03-19 deposited with the CCDC.    2019-06-05 downloaded from the CCDC.
;
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_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_max         66.693
_diffrn_reflns_theta_min         3.499
_diffrn_source                   'Cu-ImuS microfocus tube'
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         5908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0572P)^2^+0.5121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5039
_reflns_number_total             5908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07037_si_005.cif
_cod_data_source_block           nbvlf180119
_cod_database_code               4128355
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.846
_shelx_estimated_absorpt_t_max   0.912
_shelx_res_checksum              44013
_shelx_hkl_checksum              49533