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_7116371
_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         'C15 H13 N3 O, H2 O'
_chemical_formula_sum            'C15 H15 N3 O2'
_chemical_formula_weight         269.30
_chemical_name_systematic
;
 4-methyl-2-(1-phenyl-4H-1,2,4-triazol-1-ium-4-yl)phenolate hydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 112.829(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9626(9)
_cell_length_b                   4.6037(2)
_cell_length_c                   15.3349(6)
_cell_measurement_reflns_used    85
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.5
_cell_volume                     1298.91(11)
_computing_cell_refinement       EVALCCD
_computing_data_collection       Collect
_computing_data_reduction        EVALCCD
_computing_molecular_graphics    Shelxtl-Plus
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in \f and \w, 2\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7555
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.882
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       blocks
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
 Determination of absolute structure using Bayesian statistics 
 on Bijvoet differences (Hooft, Straver and Spek, 2008): 
 Hooft's y = -0.1(4) (Platon: Spek, 2009).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0381P)^2^+0.4096P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                2770
_reflns_number_total             2901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc08032g2.cif
_cod_data_source_block           schm68_m_compound_4b
_cod_database_code               7116371
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-2
_shelx_res_checksum              69987
_shelx_hkl_checksum              46374