Sulphur promoted C(sp3)-C(sp2) cross dehydrogenative cyclisation of acetophenonehydrazones with aldehydes: efficient synthesis of 3,4,5-trisubstituted 1H-pyrazoles
Rajeshwer Vanjari; Tirumaleswararao Guntreddi; Saurabh Kumar; Krishna Nand Singh; Chem.Commun. 51 (2015) 366–; doi:10.1039/C4cc08210A

data_7116367
_publ_section_title
;
 Sulphur promoted C(sp3)-C(sp2) cross dehydrogenative cyclisation of
 acetophenonehydrazones with aldehydes: efficient synthesis of
 3,4,5-trisubstituted 1H-pyrazoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              366
_journal_paper_doi               10.1039/C4cc08210A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C20 H16 N2'
_chemical_formula_weight         284.35
_chemical_name_systematic        ' 5-(naphthalen-2-yl)-3-(p-tolyl)-1H-pyrazole'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.694(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.160(2)
_cell_length_b                   5.8576(5)
_cell_length_c                   14.864(2)
_cell_measurement_reflns_used    905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1038
_cell_measurement_theta_min      3.3680
_cell_volume                     1488.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0765
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6607
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             582
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1493
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1609
_reflns_number_gt                1645
_reflns_number_total             3442
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4cc08210a2.cif
_cod_data_source_block           naph-1
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7116367