Mesomericbetaine - N-heterocyclic carbene interconversions of 1,2,4-triazolium-phenolates. Sulfur, selenium, and borane adduct formation
Ming Liu; Martin Nieger; Andreas Schmidt; Chem.Commun. 51 (2015) 477–; doi:10.1039/C4cc08032G

data_7116373
_publ_section_title
;
 Mesomericbetaine - N-heterocyclic carbene interconversions of
 1,2,4-triazolium-phenolates. Sulfur, selenium, and borane adduct
 formation
;
_journal_name_full               Chem.Commun.
_journal_page_first              477
_journal_paper_doi               10.1039/C4cc08032G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C18 H20 B N3 O1, 0.5(H2 O)'
_chemical_formula_sum            'C18 H21 B N3 O1.5'
_chemical_formula_weight         314.19
_chemical_name_systematic
4,4-diethyl-3-phenyl-4JH-benzo[e][1,2,4]triazolo[3,4-c]81,4,2]oxaza-borinin-3-ium-4-uide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                72.078(4)
_cell_angle_beta                 87.907(4)
_cell_angle_gamma                79.532(4)
_cell_formula_units_Z            4
_cell_length_a                   9.0122(4)
_cell_length_b                   11.1230(5)
_cell_length_c                   17.8748(9)
_cell_measurement_reflns_used    5167
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.94
_cell_measurement_theta_min      2.5
_cell_volume                     1676.14(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    Shelxtl-Plus
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Agilent, SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'rotation in \w, 1\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13218
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.956
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       plates
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0072(9)
_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   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0394P)^2^+0.4454P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6094
_reflns_number_total             7704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc08032g2.cif
_cod_data_source_block           schm64_compound_16a
_cod_original_formula_sum        'C18 H21 B N3 O1.50'
_cod_database_code               7116373
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-2
_shelx_res_checksum              49163
_shelx_hkl_checksum              56160