Synthesis of 1,2,4-Triazolines and Triazoles Utilizing Oxazolones
Rahman Shah Zaib Saleem; Jetze J. Tepe; Journal of Organic Chemistry 75 (2010) 4330–4332; doi:10.1021/jo100716m

data_4025500
_publ_section_title
;
 Synthesis of 1,2,4-Triazolines and Triazoles Utilizing Oxazolones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4330
_journal_page_last               4332
_journal_paper_doi               10.1021/jo100716m
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C9 H9 N3'
_chemical_formula_sum            'C9 H9 N3'
_chemical_formula_weight         159.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.1430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.97330(10)
_cell_length_b                   12.4346(2)
_cell_length_c                   8.88920(10)
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.34
_cell_measurement_theta_min      6.40
_cell_volume                     821.99(2)
_computing_cell_refinement       'APEX2 (BRUKER, V2008.5-0, 2006)'
_computing_data_collection       'COSMO (BRUKER, V1.58, 2006)'
_computing_data_reduction        'SAINT (BRUKER, V7.34A, 2006)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w,and/f 0.5 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5219
_diffrn_reflns_theta_full        67.87
_diffrn_reflns_theta_max         67.87
_diffrn_reflns_theta_min         6.40
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  0.9049
_exptl_absorpt_correction_T_min  0.8192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0105(17)
_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   1.669
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.669
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                1320
_reflns_number_total             1450
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100716m_si_005.cif
_cod_data_source_block           jjt16_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        821.990(19)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025500
_publ_contact_crystallographer_name 'Richard Staples'
_contact_crystallographer_email  xraystaples@chemistry.msu.edu.com