Catalyst-Free One-Pot Three-Component Synthesis of 4-Hydroxy-3-pyrazolylcoumarins in Ethanol at Room Temperature: Enolisable Aroylhydrazones as Efficient Ambident Nucleophile
Mukherjee, Sayan; Pramanik, Animesh; ACS Sustainable Chemistry & Engineering  (2019) –; doi:10.1021/acssuschemeng.9b05682

data_4517197
_publ_section_title
;
 Catalyst-Free One-Pot Three-Component Synthesis of
 4-Hydroxy-3-pyrazolylcoumarins in Ethanol at Room Temperature: Enolisable
 Aroylhydrazones as Efficient Ambident Nucleophile
;
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_paper_doi               10.1021/acssuschemeng.9b05682
_journal_year                    2019
_chemical_formula_sum            'C29 H16 Cl2 N2 O6 S'
_chemical_formula_weight         591.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 133.331(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.917(10)
_cell_length_b                   10.637(3)
_cell_length_c                   22.889(8)
_cell_measurement_reflns_used    1864
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.66
_cell_measurement_theta_min      2.48
_cell_volume                     5830(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13115
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        24.775
_diffrn_reflns_theta_max         24.775
_diffrn_reflns_theta_min         1.701
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.960
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2416.0
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.688
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.451
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4901
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      2.476
_refine_ls_R_factor_all          0.2384
_refine_ls_R_factor_gt           0.1638
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.1333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4236
_refine_ls_wR_factor_ref         0.4497
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2467
_reflns_number_total             4901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc9b05682_si_003.cif
_cod_data_source_block           447_a
_cod_original_cell_volume        5829(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4517197
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              47392
_shelx_hkl_checksum              70399