The search for formal electrostatic effects on molecular conformation and crystal packing: crystal structure of 2,2''-disubstituted (H <i>versus</i> PPh~2~) 1,1'-(1,2-phenylene)bis(3-methyl-1<i>H</i>-imidazol-3-ium) bis(trifluoromethanesulfonate)
Duhayon, Carine; Canac, Yves; Dubrulle, Laurent; Maaliki, Carine; Chauvin, Remi; Acta Crystallographica Section C 72 (2016) 198–202; doi:10.1107/S2053229616002576

data_2020421
_publ_section_title
;
 The search for formal electrostatic effects on molecular conformation and
 crystal packing: crystal structure of 2,2''-disubstituted (H
 <i>versus</i> PPh~2~)
 1,1'-(1,2-phenylene)bis(3-methyl-1<i>H</i>-imidazol-3-ium)
 bis(trifluoromethanesulfonate)
;
_journal_coeditor_code           EG3198
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              198
_journal_page_last               202
_journal_paper_doi               10.1107/S2053229616002576
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C14 H16 N4 2+, 2C F3 O3 S -'
_chemical_formula_moiety         'C14 H16 N4 2+, 2(C F3 O3 S -)'
_chemical_formula_sum            'C16 H16 F6 N4 O6 S2'
_chemical_formula_weight         538.45
_chemical_name_systematic
;
1,1'-(1,2-Phenylene)bis(3-methyl-1<i>H</i>-imidazol-3-ium)
bis(trifluoromethanesulfonate)
;
_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 96.0475(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.37505(13)
_cell_length_b                   16.09785(17)
_cell_length_c                   11.60677(14)
_cell_measurement_reflns_used    25125
_cell_measurement_temperature    100
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     2113.53(4)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2002)
;
_computing_data_collection
;
GEMINI (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2002)
;
_computing_molecular_graphics
;
CAMERON (Watkin <i>et al.</i>,  1996)
;
_computing_publication_material
;
CRYSTALS (Betteridge <i>et al.</i>,  2003)
;
_computing_structure_refinement
;
CRYSTALS (Betteridge <i>et al.</i>,  2003)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            63741
_diffrn_reflns_theta_full        27.127
_diffrn_reflns_theta_max         30.826
_diffrn_reflns_theta_min         3.085
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2002)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0310
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.0019719
_refine_ls_shift/su_mean         0.0000851
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial
(Watkin, 1994; Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
7.87 5.71 6.74 1.57
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0393
_refine_ls_wR_factor_gt          0.0370
_refine_ls_wR_factor_ref         0.0365
_reflns_number_gt                5692
_reflns_number_total             6255
_reflns_threshold_expression     I>2.0\s(I)
_cod_data_source_file            eg3198sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2020421.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2020421
_cod_database_fobs_code          2020421