Preparation of 3,5-disubstituted pyrazoles and isoxazoles from terminal alkynes, aldehydes, hydrazines, and hydroxylamine.
Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo; The Journal of organic chemistry 79 (2014) 2049–2058; doi:10.1021/jo4027116

data_4029162
_publ_section_title
;
 Preparation of 3,5-disubstituted pyrazoles and isoxazoles from terminal
 alkynes, aldehydes, hydrazines, and hydroxylamine.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2049
_journal_page_last               2058
_journal_paper_doi               10.1021/jo4027116
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C15 H10 Cl N O'
_chemical_formula_weight         255.69
_space_group_IT_number           2
_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                77.856(2)
_cell_angle_beta                 82.2450(10)
_cell_angle_gamma                89.7480(10)
_cell_formula_units_Z            2
_cell_length_a                   5.7192(6)
_cell_length_b                   7.2557(8)
_cell_length_c                   14.5967(16)
_cell_measurement_temperature    173(2)
_cell_volume                     586.57(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.920
_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  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3328
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.9406
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.004(3)
_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   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.2605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                1828
_reflns_number_total             2532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4027116_si_002.cif
_cod_data_source_block           a130618mor1
_cod_database_code               4029162