Azolium azolates from reactions of neutral azoles with 1,3-dimethyl-imidazolium-2-carboxylate, 1,2,3-trimethyl-imidazolium hydrogen carbonate, and N,N-dimethyl-pyrrolidinium hydrogen carbonate
Smiglak, Marcin; Hines, C. Corey; Reichert, W. Matthew; Shamshina, Julia L.; Beasley, Preston A.; McCrary, Parker D.; Kelley, Steven P.; Rogers, Robin D.; New Journal of Chemistry 37 (2013) 1461–; doi:10.1039/c3nj00147d

data_7053133
_publ_section_title
;
 Azolium azolates from reactions of neutral azoles with
 1,3-dimethyl-imidazolium-2-carboxylate, 1,2,3-trimethyl-imidazolium
 hydrogen carbonate, and N,N-dimethyl-pyrrolidinium hydrogen carbonate
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1461
_journal_paper_doi               10.1039/c3nj00147d
_journal_volume                  37
_journal_year                    2013
_chemical_formula_sum            'C18 H26 N10 O4'
_chemical_formula_weight         446.49
_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                74.659(3)
_cell_angle_beta                 74.897(3)
_cell_angle_gamma                68.180(3)
_cell_formula_units_Z            1
_cell_length_a                   6.9280(13)
_cell_length_b                   8.2326(15)
_cell_length_c                   10.864(2)
_cell_measurement_reflns_used    1456
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.71
_cell_volume                     545.56(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3708
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SHELX SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.1266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1289
_reflns_number_gt                1836
_reflns_number_total             2473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3nj00147d.txt
_cod_data_source_block           '[1,3-diMe-Im][2-Me-5-NO2-Im]'
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        545.57(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7053133