Pyrido[1,2-a][1,2,4]triazol-3-ylidenes as a New Family of Stable Annulated N-Heterocyclic Carbenes: Synthesis, Reactivity, and Their Application in Coordination Chemistry and Organocatalysis
Yajun Ma; Siping Wei; Jingbo Lan; Jingzhi Wang; Rugang Xie; Jingsong You; Journal of Organic Chemistry 73 (2008) 8256–8264; doi:10.1021/jo801349d

data_4023792
_publ_section_title
;
 Pyrido[1,2-a][1,2,4]triazol-3-ylidenes as a New Family of Stable
 Annulated N-Heterocyclic Carbenes: Synthesis, Reactivity, and Their
 Application in Coordination Chemistry and Organocatalysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8256
_journal_page_last               8264
_journal_paper_doi               10.1021/jo801349d
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         C8H9N3S
_chemical_formula_sum            'C8 H9 N3 S'
_chemical_formula_weight         179.24
_chemical_name_common            2-Ethyl-pyrido[1,2-a][1,2,4]-triazol-3-thione
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 111.03(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.706(3)
_cell_length_b                   20.431(9)
_cell_length_c                   6.9139(19)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      7.68
_cell_measurement_theta_min      4.69
_cell_volume                     884.2(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'ENRAF-NONIUS CAD4'
_diffrn_measurement_method       Omega/2-Theta
_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  0.0080
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            1856
_diffrn_reflns_theta_full        25.45
_diffrn_reflns_theta_max         25.45
_diffrn_reflns_theta_min         3.31
_diffrn_standards_decay_%        0.397
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       acerate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0582P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                992
_reflns_number_total             1628
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801349d_si_003.cif
_cod_data_source_block           cd16
_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:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4023792