Pairing heterocyclic cations with closo-icosahedral borane and carborane anions. i. benchtop aqueous synthesis of binary triazolium and imidazolium salts with limited water solubility.
Shackelford, Scott A.; Belletire, John L.; Boatz, Jerry A.; Schneider, Stefan; Wheaton, Amanda K.; Wight, Brett A.; Hudgens, Leslie M.; Ammon, Herman L.; Strauss, Steven H.; Organic letters 11 (2009) 2623–2626; doi:10.1021/ol900550v

data_1503885
_publ_section_title
;
 Pairing heterocyclic cations with closo-icosahedral borane and carborane
 anions. i. benchtop aqueous synthesis of binary triazolium and
 imidazolium salts with limited water solubility.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2623
_journal_page_last               2626
_journal_paper_doi               10.1021/ol900550v
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C4 H26 B12 N8 O2'
_chemical_formula_weight         348.05
_chemical_name_common            '[(1-Am-3-H-1,2,3-Triaz)]2B12H12.(H2O)2'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.048(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3950(5)
_cell_length_b                   16.8827(12)
_cell_length_c                   7.3580(7)
_cell_measurement_temperature    296(2)
_cell_volume                     911.69(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.616
_diffrn_measured_fraction_theta_max 0.616
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3124
_diffrn_reflns_theta_full        64.73
_diffrn_reflns_theta_max         64.73
_diffrn_reflns_theta_min         5.24
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.060(6)
_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   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1022P)^2^+0.0811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                936
_reflns_number_total             958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900550v_si_002.cif
_cod_data_source_block           3
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1503885