9-(2,6-Difluorophenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate and its precursor 2,6-difluorophenyl acridine-9-carboxylate: C—H···O, C—F···π, S—O···π and π‒π stacking interactions
Artur Sikorski; Karol Krzymiński; Agnieszka Niziołek; Jerzy Błażejowski; Acta Crystallographica Section C 61 (2005) o690–o694; doi:10.1107/S0108270105033779

data_2015174
_publ_section_title
;
 9-(2,6-Difluorophenoxycarbonyl)-10-methylacridinium
 trifluoromethanesulfonate and its precursor 2,6-difluorophenyl
 acridine-9-carboxylate: C---H&#x00B7;&#x00B7;&#x00B7;O,
 C---F&#x00B7;&#x00B7;&#x00B7;\p, S---O&#x00B7;&#x00B7;&#x00B7;\p and
 \p--\p stacking interactions
;
_journal_coeditor_code           LN1184
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o690
_journal_page_last               o694
_journal_paper_doi               10.1107/S0108270105033779
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C21 H14 F2 N O2 + , C F3 O3 S -'
_chemical_formula_moiety         'C21 H14 F2 N O2 + , C F3 O3 S -'
_chemical_formula_sum            'C22 H14 F5 N O5 S'
_chemical_formula_weight         499.40
_chemical_name_systematic
;
9-(2,6-difluorophenoxycarbonyl)-10-methylacridinium 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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.16(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.382(2)
_cell_length_b                   14.048(3)
_cell_length_c                   13.162(3)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.12
_cell_volume                     2104.1(8)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma Diffraction, 1989)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       \q/2\q
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3874
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        4.45
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       prism
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.321
_refine_ls_extinction_coef       0.0096(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0693P)^2^+0.9523P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                1760
_reflns_number_total             3700
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ln1184.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015174