##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2009-01-28
_journal_date_accepted     2009-03-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      4
_journal_page_first     o768
_journal_page_last     o769
_journal_paper_category     QO
_journal_coeditor_code     XU2477
_publ_contact_author_name     'Prof Jerzy Błażejowski'
_publ_contact_author_address
;
Faculty of Chemistry
University of Gdańsk
J. Sobieskiego 18
80-952 Gdańsk
Poland
;
_publ_contact_author_email     bla@chem.univ.gda.pl
_publ_contact_author_fax     '+48 58 523 53 57'
_publ_contact_author_phone     '+48 58 523 53 31'
_publ_section_title
;
9-Chloro-2,4-dimethoxyacridinium trifluoromethanesulfonate
;
loop_
    _publ_author_name
    _publ_author_address
    'Beata Zadykowicz'
;
Faculty of Chemistry
University of Gdańsk
J. Sobieskiego 18
80-952 Gdańsk
Poland
;
    'Karol Krzymiński'
;
Faculty of Chemistry
University of Gdańsk
J. Sobieskiego 18
80-952 Gdańsk
Poland
;
    'Damian Trzybiński'
;
Faculty of Chemistry
University of Gdańsk
J. Sobieskiego 18
80-952 Gdańsk
Poland
;
    'Artur Sikorski'
;
Faculty of Chemistry
University of Gdańsk
J. Sobieskiego 18
80-952 Gdańsk
Poland
;
    'Jerzy Błażejowski'
;
Faculty of Chemistry
University of Gdańsk
J. Sobieskiego 18
80-952 Gdańsk
Poland
;
data_I
_chemical_name_systematic
;
9-Chloro-2,4-dimethoxyacridinium trifluoromethanesulfonate
;
_chemical_formula_moiety     'C15 H13 Cl N O2 +, C F3 O3 S1 -'
_chemical_formula_sum     'C16 H13 Cl F3 N O5 S'
_chemical_formula_iupac     'C15 H13 Cl N O2 +, C F3 S O3 -'
_chemical_formula_weight     423.79
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y+1/2, z+1/2'
_cell_length_a     11.0502(9)
_cell_length_b     23.110(2)
_cell_length_c     7.1435(8)
_cell_angle_alpha     90.00
_cell_angle_beta     108.214(11)
_cell_angle_gamma     90.00
_cell_volume     1732.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5776
_cell_measurement_theta_min     2.9928
_cell_measurement_theta_max     29.1557
_cell_measurement_temperature     295(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     purple
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.625
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     864
_exptl_absorpt_coefficient_mu     0.401
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2008)
;
_exptl_absorpt_correction_T_min     0.782
_exptl_absorpt_correction_T_max     0.959
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini R Ultra Ruby CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.4002
_diffrn_reflns_number     12548
_diffrn_reflns_av_R_equivalents     0.0634
_diffrn_reflns_av_sigmaI/netI     0.0408
_diffrn_reflns_theta_min     3.13
_diffrn_reflns_theta_max     25.10
_diffrn_reflns_theta_full     25.10
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3072
_reflns_number_gt     1932
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0856
_refine_ls_R_factor_gt     0.0579
_refine_ls_wR_factor_gt     0.1674
_refine_ls_wR_factor_ref     0.1794
_refine_ls_goodness_of_fit_ref     1.056
_refine_ls_restrained_S_all     1.056
_refine_ls_number_reflns     3072
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                'calc w=1/[σ²(Fo²)+(0.1062P)²P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.408
_refine_diff_density_min     -0.275
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 1.1372(3) 0.84277(15) 0.6837(5) 0.0588(9) Uani d . 1 . .
    H H1 1.2152 0.8604 0.7447 0.071 Uiso calc R 1 . .
    C C2 1.0316(3) 0.87560(16) 0.6029(5) 0.0630(9) Uani d . 1 . .
    C C3 0.9120(3) 0.85005(15) 0.5039(5) 0.0606(9) Uani d . 1 . .
    H H3 0.8414 0.8734 0.4478 0.073 Uiso calc R 1 . .
    C C4 0.9004(3) 0.79165(14) 0.4907(5) 0.0539(8) Uani d . 1 . .
    C C5 1.0717(4) 0.60054(16) 0.6391(5) 0.0672(9) Uani d . 1 . .
    H H5 0.9905 0.5857 0.5802 0.081 Uiso calc R 1 . .
    C C6 1.1712(4) 0.56449(18) 0.7170(6) 0.0774(11) Uani d . 1 . .
    H H6 1.1578 0.5247 0.7103 0.093 Uiso calc R 1 . .
    C C7 1.2939(4) 0.5859(2) 0.8075(6) 0.0824(12) Uani d . 1 . .
    H H7 1.3608 0.5603 0.8595 0.099 Uiso calc R 1 . .
    C C8 1.3169(4) 0.64432(19) 0.8204(6) 0.0740(10) Uani d . 1 . .
    H H8 1.3990 0.6579 0.8812 0.089 Uiso calc R 1 . .
    C C9 1.2292(3) 0.74378(17) 0.7518(5) 0.0586(9) Uani d . 1 . .
    N N10 0.9955(2) 0.69822(11) 0.5708(4) 0.0525(7) Uani d . 1 . .
    H H10 0.9213 0.6840 0.5128 0.063 Uiso calc R 1 . .
    C C11 1.1281(3) 0.78210(15) 0.6748(4) 0.0532(8) Uani d . 1 . .
    C C12 1.0075(3) 0.75623(14) 0.5787(4) 0.0507(8) Uani d . 1 . .
    C C13 1.2163(3) 0.68400(16) 0.7418(5) 0.0606(9) Uani d . 1 . .
    C C14 1.0924(3) 0.66091(15) 0.6481(4) 0.0552(8) Uani d . 1 . .
    O O15 1.0275(2) 0.93401(11) 0.6023(4) 0.0789(8) Uani d . 1 . .
    C C16 1.1437(4) 0.96502(17) 0.6957(6) 0.0822(11) Uani d . 1 . .
    H H16A 1.1261 1.0057 0.6933 0.123 Uiso calc R 1 . .
    H H16B 1.2038 0.9577 0.6263 0.123 Uiso calc R 1 . .
    H H16C 1.1787 0.9523 0.8298 0.123 Uiso calc R 1 . .
    O O17 0.7946(2) 0.76076(10) 0.3978(4) 0.0661(7) Uani d . 1 . .
    C C18 0.6815(3) 0.79154(16) 0.2905(6) 0.0708(10) Uani d . 1 . .
    H H18A 0.6146 0.7644 0.2313 0.106 Uiso calc R 1 . .
    H H18B 0.6985 0.8145 0.1894 0.106 Uiso calc R 1 . .
    H H18C 0.6557 0.8164 0.3789 0.106 Uiso calc R 1 . .
    Cl Cl19 1.37790(8) 0.77318(5) 0.86037(16) 0.0835(4) Uani d . 1 . .
    S S20 0.67506(9) 0.60826(4) 0.27655(15) 0.0686(4) Uani d . 1 . .
    O O21 0.7046(4) 0.56795(15) 0.1495(6) 0.1301(14) Uani d . 1 . .
    O O22 0.5948(3) 0.65462(13) 0.1825(5) 0.1074(11) Uani d . 1 . .
    O O23 0.7793(2) 0.62580(14) 0.4408(5) 0.0967(9) Uani d . 1 . .
    C C24 0.5785(4) 0.56702(17) 0.3904(6) 0.0738(10) Uani d . 1 . .
    F F25 0.6355(3) 0.52276(13) 0.4837(5) 0.1314(12) Uani d . 1 . .
    F F26 0.5357(4) 0.59810(14) 0.5057(6) 0.1486(14) Uani d . 1 . .
    F F27 0.4759(3) 0.54695(15) 0.2592(5) 0.1493(14) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.360(5) ?
    C1 C11 . 1.405(5) ?
    C1 H1 . 0.9300 ?
    C2 O15 . 1.351(4) ?
    C2 C3 . 1.418(5) ?
    C3 C4 . 1.356(5) ?
    C3 H3 . 0.9300 ?
    C4 O17 . 1.354(4) ?
    C4 C12 . 1.414(4) ?
    C5 C6 . 1.353(5) ?
    C5 C14 . 1.412(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.398(6) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.370(6) ?
    C7 H7 . 0.9300 ?
    C8 C13 . 1.415(5) ?
    C8 H8 . 0.9300 ?
    C9 C13 . 1.388(5) ?
    C9 C11 . 1.396(5) ?
    C9 Cl19 . 1.723(3) ?
    N10 C12 . 1.346(4) ?
    N10 C14 . 1.351(4) ?
    N10 H10 . 0.8600 ?
    C11 C12 . 1.426(4) ?
    C13 C14 . 1.427(5) ?
    O15 C16 . 1.439(4) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    O17 C18 . 1.434(4) ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    S20 O21 . 1.408(3) ?
    S20 O22 . 1.419(3) ?
    S20 O23 . 1.422(3) ?
    S20 C24 . 1.803(4) ?
    C24 F25 . 1.275(4) ?
    C24 F26 . 1.289(4) ?
    C24 F27 . 1.310(5) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C11 . . 119.9(3) ?
    C2 C1 H1 . . 120.1 ?
    C11 C1 H1 . . 120.1 ?
    O15 C2 C1 . . 125.6(3) ?
    O15 C2 C3 . . 112.9(3) ?
    C1 C2 C3 . . 121.4(3) ?
    C4 C3 C2 . . 120.1(3) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    O17 C4 C3 . . 127.4(3) ?
    O17 C4 C12 . . 112.8(3) ?
    C3 C4 C12 . . 119.9(3) ?
    C6 C5 C14 . . 119.4(4) ?
    C6 C5 H5 . . 120.3 ?
    C14 C5 H5 . . 120.3 ?
    C5 C6 C7 . . 121.2(4) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    C8 C7 C6 . . 120.9(4) ?
    C8 C7 H7 . . 119.6 ?
    C6 C7 H7 . . 119.6 ?
    C7 C8 C13 . . 120.4(4) ?
    C7 C8 H8 . . 119.8 ?
    C13 C8 H8 . . 119.8 ?
    C13 C9 C11 . . 123.7(3) ?
    C13 C9 Cl19 . . 118.9(3) ?
    C11 C9 Cl19 . . 117.4(3) ?
    C12 N10 C14 . . 124.3(3) ?
    C12 N10 H10 . . 117.9 ?
    C14 N10 H10 . . 117.9 ?
    C9 C11 C1 . . 125.3(3) ?
    C9 C11 C12 . . 115.8(3) ?
    C1 C11 C12 . . 118.8(3) ?
    N10 C12 C4 . . 120.0(3) ?
    N10 C12 C11 . . 120.2(3) ?
    C4 C12 C11 . . 119.8(3) ?
    C9 C13 C8 . . 124.7(3) ?
    C9 C13 C14 . . 117.7(3) ?
    C8 C13 C14 . . 117.6(4) ?
    N10 C14 C5 . . 121.1(3) ?
    N10 C14 C13 . . 118.3(3) ?
    C5 C14 C13 . . 120.6(3) ?
    C2 O15 C16 . . 118.2(3) ?
    O15 C16 H16A . . 109.5 ?
    O15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C4 O17 C18 . . 118.4(3) ?
    O17 C18 H18A . . 109.5 ?
    O17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O17 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    O21 S20 O22 . . 115.5(2) ?
    O21 S20 O23 . . 115.4(2) ?
    O22 S20 O23 . . 113.59(19) ?
    O21 S20 C24 . . 103.3(2) ?
    O22 S20 C24 . . 104.03(19) ?
    O23 S20 C24 . . 102.66(19) ?
    F25 C24 F26 . . 109.4(4) ?
    F25 C24 F27 . . 105.4(4) ?
    F26 C24 F27 . . 104.2(4) ?
    F25 C24 S20 . . 113.3(3) ?
    F26 C24 S20 . . 112.4(3) ?
    F27 C24 S20 . . 111.5(3) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C11 C1 C2 O15 . . . . 179.7(3) ?
    C11 C1 C2 C3 . . . . -1.8(5) ?
    O15 C2 C3 C4 . . . . 179.7(3) ?
    C1 C2 C3 C4 . . . . 1.1(5) ?
    C2 C3 C4 O17 . . . . -178.2(3) ?
    C2 C3 C4 C12 . . . . 1.0(5) ?
    C14 C5 C6 C7 . . . . 0.5(6) ?
    C5 C6 C7 C8 . . . . 0.2(6) ?
    C6 C7 C8 C13 . . . . -0.1(6) ?
    C13 C9 C11 C1 . . . . 179.4(3) ?
    Cl19 C9 C11 C1 . . . . -2.0(4) ?
    C13 C9 C11 C12 . . . . -1.2(4) ?
    Cl19 C9 C11 C12 . . . . 177.4(2) ?
    C2 C1 C11 C9 . . . . 180.0(3) ?
    C2 C1 C11 C12 . . . . 0.6(5) ?
    C14 N10 C12 C4 . . . . 179.1(3) ?
    C14 N10 C12 C11 . . . . -0.6(4) ?
    O17 C4 C12 N10 . . . . -2.6(4) ?
    C3 C4 C12 N10 . . . . 178.1(3) ?
    O17 C4 C12 C11 . . . . 177.1(3) ?
    C3 C4 C12 C11 . . . . -2.2(4) ?
    C9 C11 C12 N10 . . . . 1.7(4) ?
    C1 C11 C12 N10 . . . . -178.9(3) ?
    C9 C11 C12 C4 . . . . -178.0(3) ?
    C1 C11 C12 C4 . . . . 1.4(4) ?
    C11 C9 C13 C8 . . . . -179.3(3) ?
    Cl19 C9 C13 C8 . . . . 2.0(5) ?
    C11 C9 C13 C14 . . . . -0.3(5) ?
    Cl19 C9 C13 C14 . . . . -179.0(2) ?
    C7 C8 C13 C9 . . . . 178.3(3) ?
    C7 C8 C13 C14 . . . . -0.7(5) ?
    C12 N10 C14 C5 . . . . 178.1(3) ?
    C12 N10 C14 C13 . . . . -1.1(4) ?
    C6 C5 C14 N10 . . . . 179.6(3) ?
    C6 C5 C14 C13 . . . . -1.2(5) ?
    C9 C13 C14 N10 . . . . 1.5(4) ?
    C8 C13 C14 N10 . . . . -179.5(3) ?
    C9 C13 C14 C5 . . . . -177.7(3) ?
    C8 C13 C14 C5 . . . . 1.3(5) ?
    C1 C2 O15 C16 . . . . -0.5(5) ?
    C3 C2 O15 C16 . . . . -179.0(3) ?
    C3 C4 O17 C18 . . . . 3.6(5) ?
    C12 C4 O17 C18 . . . . -175.7(3) ?
    O21 S20 C24 F25 . . . . 59.0(4) ?
    O22 S20 C24 F25 . . . . -180.0(3) ?
    O23 S20 C24 F25 . . . . -61.4(4) ?
    O21 S20 C24 F26 . . . . -176.3(4) ?
    O22 S20 C24 F26 . . . . -55.3(4) ?
    O23 S20 C24 F26 . . . . 63.3(4) ?
    O21 S20 C24 F27 . . . . -59.7(4) ?
    O22 S20 C24 F27 . . . . 61.3(4) ?
    O23 S20 C24 F27 . . . . 179.9(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N10 H10 O23 . 0.86 2.01 2.826(4) 159 y
    C5 H5 O23 . 0.93 2.42 3.151(5) 136 y
    C8 H8 O22 1_656 0.93 2.53 3.348(6) 147 y
    C18 H18A O22 . 0.96 2.56 3.326(5) 137 y
    C18 H18C O22 4_565 0.96 2.55 3.462(5) 158 y
