A metal-free tandem approach to prepare structurally diverse N-heterocycles: synthesis of 1,2,4-oxadiazoles and pyrimidinones
Gupta, Puneet K.; Hussain, Mohd. Kamil; Asad, Mohd.; Kant, Ruchir; Mahar, Rohit; Shukla, Sanjeev K.; Hajela, Kanchan; New Journal of Chemistry 38 (2014) 3062–; doi:10.1039/c4nj00361f

data_7054118
_publ_section_title
;
 A metal-free tandem approach to prepare structurally diverse
 N-heterocycles: synthesis of 1,2,4-oxadiazoles and pyrimidinones
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3062
_journal_paper_doi               10.1039/c4nj00361f
_journal_volume                  38
_journal_year                    2014
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C16 H14 N2 O3'
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90
_cell_angle_beta                 119.49(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.558(5)
_cell_length_b                   11.363(4)
_cell_length_c                   17.351(4)
_cell_measurement_reflns_used    3792
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      3.0
_cell_volume                     2841.6(16)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21437
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         3.31
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       ' Block'
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0969P)^2^+0.0162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1663
_reflns_number_gt                4160
_reflns_number_total             5152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj00361f2.cif
_cod_data_source_block           xxx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'Constr' changed
to 'constr' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7054118.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7054118