[Et3NH][HSO4]-mediated functionalization of hippuric acid: an unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones
Parveen, Mehtab; Ahmad, Faheem; Malla, Ali Mohammed; Azaz, Shaista; Silva, Manuela Ramos; Silva, P. S. Pereira; RSC Adv.  (2015) –; doi:10.1039/C5RA09290F

data_7220744
_publ_section_title
;
 [Et3NH][HSO4]-mediated functionalization of hippuric acid: an
 unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA09290F
_journal_year                    2015
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2014-12-16 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.0550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0978(3)
_cell_length_b                   3.97900(10)
_cell_length_c                   15.5788(4)
_cell_measurement_reflns_used    5834
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6960
_cell_measurement_theta_min      2.6557
_cell_volume                     738.40(3)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
Mercury (Macrae et al., 2006) and PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX2 CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13647
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.048
_diffrn_reflns_theta_min         3.401
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   (SADABS;Sheldrick,2003)
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 953 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.0436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2503
_reflns_number_total             2873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra09290f2.cif
_cod_data_source_block           shelx
_cod_database_code               7220744
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              57306
_shelx_hkl_checksum              87472