Phase-out-compliant fluorosurfactants: Unique methimazolium derivatives including room temperature ionic liquids
Hummel, Michael; Markiewicz, Marta; Stolte, Stefan; Noisternig, Michael Franz; Braun, Doris Elfriede; Gelbrich, Thomas; Griesser, Ulrich J.; Partl, Gabriel Julian; Naier, Benjamin Florian; Wurst, Klaus; Krüger, Biljana; Kopacka, Holger; Laus, Gerhard; Huppertz, Hubert; Schottenberger, Herwig; Green Chem.  (2017) –; doi:10.1039/C7GC00571G

data_7227986
_publ_section_title
;
 Phase-out-compliant fluorosurfactants: Unique methimazolium derivatives
 including room temperature ionic liquids
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC00571G
_journal_year                    2017
_chemical_formula_moiety         'C12 H10 F13 N2 S 1+, Cl 1-'
_chemical_formula_sum            'C12 H10 Cl F13 N2 S'
_chemical_formula_weight         496.73
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-01-25 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                75.231(5)
_cell_angle_beta                 83.709(5)
_cell_angle_gamma                76.855(5)
_cell_formula_units_Z            2
_cell_length_a                   6.3654(4)
_cell_length_b                   9.2363(5)
_cell_length_c                   16.0361(12)
_cell_measurement_reflns_used    3049
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.2210
_cell_measurement_theta_min      3.8980
_cell_measurement_wavelength     0.71073
_cell_volume                     886.44(10)
_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_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3575
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13865
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.937
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88894
_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    1.861
_exptl_crystal_description       'platy fragment'
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3236
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0498P)^2^+0.6803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2536
_reflns_number_total             3236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc00571g2.cif
_cod_data_source_block           shelx
_cod_database_code               7227986
_shelx_estimated_absorpt_t_min   0.836
_shelx_estimated_absorpt_t_max   0.973
_shelxl_version_number           2014/6
_shelx_res_checksum              82645
_shelx_hkl_checksum              44383