Synthesis of 3-Hydroxy-6-oxo[1,2,4]triazin-1-yl Alaninamides, a New Class of Cyclic Dipeptidyl Ureas
María Sañudo; Stefano Marcaccini; Sara Basurto; Tomás Torroba; Journal of Organic Chemistry 71 (2006) 4578–4584; doi:10.1021/jo060434y

data_4021743
_publ_contact_author_address
;University of Burgos
Department of Chemistry
Faculty of Science
09001 Burgos, Spain
;
_publ_contact_author_email       ttorroba@ubu.es
_publ_contact_author_fax         +34947258087
_publ_contact_author_name        'Tomas Torroba'
_publ_contact_author_phone       +34947258088
_publ_section_title
;
 Synthesis of 3-Hydroxy-6-oxo[1,2,4]triazin-1-yl Alaninamides,
 a New Class of Cyclic Dipeptidyl Ureas
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4578
_journal_page_last               4584
_journal_paper_doi               10.1021/jo060434y
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C19 H24 N4 O3'
_chemical_formula_sum            'C19 H24 N4 O3'
_chemical_formula_weight         356.42
_chemical_melting_point          488.6(5)
_chemical_name_common            5a
_chemical_name_systematic
;
N-Cyclohexyl-2-(3-hydroxy-6-oxo-5-
phenyl-6H-[1,2,4]triazin-1-yl)isobutyramide
;
_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                 116.880(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.367(4)
_cell_length_b                   15.514(5)
_cell_length_c                   11.871(4)
_cell_measurement_reflns_used    1228
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.01
_cell_measurement_theta_min      2.33
_cell_volume                     1867.2(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0802
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18241
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.8568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (SHELDRICK, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0788
_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^)+(0.1478P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2226
_refine_ls_wR_factor_ref         0.2495
_reflns_number_gt                2047
_reflns_number_total             3472
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060434ysi20060302_124314.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '215-216_C' was changed to '488.6(5)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021743