Efficient synthesis of 1,2-bis(alkoxycarbonyl)pyrazol-3-ones from 2,3-allenoic acids, azodicarboxylates and PPh3
Ruizhi Lu; Xin Cheng; Xingliang Zheng; Shengming Ma; Chem.Commun. 50 (2014) 1537–; doi:10.1039/c3cc48215d

data_7111859
_publ_section_title
;
 Efficient synthesis of 1,2-bis(alkoxycarbonyl)pyrazol-3-ones from
 2,3-allenoic acids, azodicarboxylates and PPh3
;
_journal_name_full               Chem.Commun.
_journal_page_first              1537
_journal_paper_doi               10.1039/c3cc48215d
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C27 H34 N2 O5'
_chemical_formula_weight         466.56
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.689(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4117(13)
_cell_length_b                   11.1267(10)
_cell_length_c                   16.3730(15)
_cell_measurement_reflns_used    2463
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.763
_cell_measurement_theta_min      4.638
_cell_volume                     2620.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13483
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75854
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0042(13)
_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   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4874
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1031P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1841
_refine_ls_wR_factor_ref         0.2025
_reflns_number_gt                2941
_reflns_number_total             4874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48215d.txt
_cod_data_source_block           cd2805
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7111859