Copper-Catalyzed Double C‒H Alkylation of Aldehyde-Derived N,N-Dialkylhydrazones with Polyhalomethanes: Flexible Access to 4-Functionalized Pyrazoles
Prieto, Alexis; Bouyssi, Didier; Monteiro, Nuno; ACS Catalysis 6 (2016) 7197–; doi:10.1021/acscatal.6b02439

data_4516715
_publ_section_title
;
 Copper-Catalyzed Double C--H Alkylation of Aldehyde-Derived
 N,N-Dialkylhydrazones with Polyhalomethanes: Flexible Access to
 4-Functionalized Pyrazoles
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              7197
_journal_paper_doi               10.1021/acscatal.6b02439
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C16 H15 N3 O4'
_chemical_formula_sum            'C16 H15 N3 O4'
_chemical_formula_weight         313.31
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90.0
_cell_angle_beta                 91.548(8)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.2029(10)
_cell_length_b                   19.4064(18)
_cell_length_c                   7.7687(7)
_cell_measurement_reflns_used    2401
_cell_measurement_temperature    293
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     1537.7(2)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8560
_diffrn_reflns_theta_full        25.013
_diffrn_reflns_theta_max         29.428
_diffrn_reflns_theta_min         2.825
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.411
_exptl_crystal_size_min          0.384
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.22
_refine_ls_extinction_coef       130(50)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0440
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.0003075
_refine_ls_shift/su_mean         0.0000242
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 19.5 -2.27 16.6 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1030
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0724
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                2458
_reflns_number_total             3682
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0572
_oxford_refine_ls_scale          7.78(3)
_oxford_reflns_number_all        3673
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            cs6b02439_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4516715
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;