Rh(III)-catalyzed intermolecular C-H amination of 1-aryl-1H-pyrazol-5(4H)-ones with alkylamines.
Wu, Kui; Fan, Zhoulong; Xue, Yu; Yao, Qizheng; Zhang, Ao; Organic letters 16 (2014) 42–45; doi:10.1021/ol402965d

data_1513520
_publ_section_title
;
 Rh(III)-catalyzed intermolecular C-H amination of
 1-aryl-1H-pyrazol-5(4H)-ones with alkylamines.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              42
_journal_page_last               45
_journal_paper_doi               10.1021/ol402965d
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C15 H19 N3 O2'
_chemical_formula_weight         273.33
_space_group_IT_number           1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.678(12)
_cell_angle_beta                 79.658(10)
_cell_angle_gamma                83.356(11)
_cell_formula_units_Z            2
_cell_length_a                   8.665(5)
_cell_length_b                   8.848(5)
_cell_length_c                   10.375(6)
_cell_measurement_temperature    296(2)
_cell_volume                     752.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4512
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             299
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_extinction_coef       0.068(18)
_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   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.1075
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2938
_refine_ls_wR_factor_ref         0.3161
_reflns_number_gt                2715
_reflns_number_total             4011
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402965d_si_002.cif
_cod_data_source_block           2013314_0m
_cod_original_cell_volume        752.8(7)
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1513520