Synthesis of 2-aryl-2H,4H-imidazo[4,5-d][1,2,3]triazoles from triethyl N-(1-ethyl-2-methyl-4-nitro-1H-imidazol-5-yl)phosphorimidate by reaction with aryl isocyanates
Taher, Abutariq; Eichenseher, Sandra; Slawin, Alexandra M. Z.; Tennant, George; Weaver, George W.; Journal of the Chemical Society, Perkin Transactions 1  (2002) 1968–; doi:10.1039/b205216b

data_7204471
_publ_section_title
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 Synthesis of 2-aryl-2H,4H-imidazo[4,5-d][1,2,3]triazoles from triethyl
 N-(1-ethyl-2-methyl-4-nitro-1H-imidazol-5-yl)phosphorimidate by
 reaction with aryl isocyanates
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_journal_issue                   17
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1968
_journal_paper_doi               10.1039/b205216b
_journal_year                    2002
_chemical_formula_moiety         'C13 H12 F3 N5'
_chemical_formula_sum            'C13 H12 F3 N5'
_chemical_formula_weight         295.28
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.99(2)
_cell_angle_beta                 100.84(2)
_cell_angle_gamma                91.560(10)
_cell_formula_units_Z            2
_cell_length_a                   7.188(2)
_cell_length_b                   9.088(2)
_cell_length_c                   10.682(2)
_cell_measurement_reflns_used    11
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.1
_cell_measurement_theta_min      6.5
_cell_volume                     685.0(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC7S'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0031
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2231
_diffrn_reflns_theta_full        60.02
_diffrn_reflns_theta_max         60.02
_diffrn_reflns_theta_min         4.21
_diffrn_standards_decay_%        -0.16
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.032
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   semi-empirical
_exptl_crystal_colour            colurless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0092(16)
_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   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.3304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1656
_reflns_number_gt                1467
_reflns_number_total             2023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b205216b.txt
_cod_data_source_block           4c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
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_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204471