Ambident reactivity of 5-aminopyrazoles towards donor–acceptor cyclopropanes
Vartanova, Anna E.; Levina, Irina I.; Ratmanova, Nina K.; Andreev, Ivan A.; Ivanova, Olga A.; Trushkov, Igor V.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01490D

data_7158893
_publ_section_title
;
 Ambident reactivity of 5-aminopyrazoles towards donor--acceptor
 cyclopropanes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01490D
_journal_year                    2022
_chemical_formula_moiety         'C16 H19 N3 O'
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                100.610(3)
_cell_angle_beta                 92.588(3)
_cell_angle_gamma                94.229(3)
_cell_formula_units_Z            2
_cell_length_a                   5.1190(5)
_cell_length_b                   11.5332(11)
_cell_length_c                   11.6739(11)
_cell_measurement_reflns_used    7216
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.62
_cell_measurement_theta_min      2.28
_cell_volume                     674.37(11)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_structure_refinement
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_structure_solution
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       '\w shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25877
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         1.803
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_current           30
_diffrn_source_power             50
_diffrn_source_size              '0.6 mm, fine-focus'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0762P)^2^+0.4225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1618
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2784
_reflns_number_total             3942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01490d2.cif
_cod_data_source_block           Z-617
_cod_database_code               7158893
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              1871
_shelx_hkl_checksum              22629