#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/62/2206273.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206273
loop_
_publ_author_name
'Artur Sikorski'
'Karol Krzymiński'
'Antoni Konitz'
'Jerzy Błażejowski'
_publ_section_title
;
 9-(2,6-Dibromophenoxycarbonyl)-10-methylacridinium
 trifluoromethanesulfonate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2131
_journal_page_last               o2133
_journal_paper_doi               10.1107/S1600536805017952
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C21 H14 Br2 N O2 + , C F3 O3 S -'
_chemical_formula_moiety         'C21 H14 Br2 N O2 + , C F3 O3 S -'
_chemical_formula_sum            'C22 H14 Br2 F3 N O5 S'
_chemical_formula_weight         621.21
_chemical_name_systematic
;
9-(2,6-Dibromophenoxycarbonyl)-10-methylacridinium
trifluoromethanesulfonate
;
_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
_cell_angle_alpha                105.83(3)
_cell_angle_beta                 103.87(3)
_cell_angle_gamma                107.40(3)
_cell_formula_units_Z            2
_cell_length_a                   9.414(2)
_cell_length_b                   11.041(2)
_cell_length_c                   12.347(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.08
_cell_volume                     1103.7(6)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Kuma KM4'
_diffrn_measurement_method       θ/2θ
_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  0.0756
_diffrn_reflns_av_sigmaI/netI    0.1261
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4059
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        2.98
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.829
_exptl_absorpt_correction_T_max  0.465
_exptl_absorpt_correction_T_min  0.280
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.441
_refine_ls_extinction_coef       0.0042(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.1470
_refine_ls_R_factor_gt           0.0461
_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/[σ²(Fo²)+(0.0687P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                1691
_reflns_number_total             3860
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6089.cif
_cod_data_source_block           I
_cod_database_code               2206273
_cod_database_fobs_code          2206273
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C1 0.0728(6) 0.8038(6) 0.5273(5) 0.0356(14) Uani d . 1 C
H1 0.1605 0.7989 0.5072 0.043 Uiso d R 1 H
C2 0.0642(8) 0.7963(6) 0.6335(5) 0.0443(16) Uani d . 1 C
H2 0.1439 0.7833 0.6844 0.053 Uiso d R 1 H
C3 -0.0681(7) 0.8039(6) 0.6667(6) 0.0423(15) Uani d . 1 C
H3 -0.0732 0.7999 0.7400 0.051 Uiso d R 1 H
C4 -0.1884(7) 0.8172(6) 0.5919(5) 0.0431(16) Uani d . 1 C
H4 -0.2735 0.8243 0.6152 0.052 Uiso d R 1 H
C5 -0.4131(7) 0.8916(6) 0.2332(6) 0.0514(17) Uani d . 1 C
H5 -0.4970 0.8981 0.2583 0.062 Uiso d R 1 H
C6 -0.4029(8) 0.9078(7) 0.1302(6) 0.0542(18) Uani d . 1 C
H6 -0.4739 0.9383 0.0908 0.065 Uiso d R 1 H
C7 -0.2829(8) 0.8906(7) 0.0883(6) 0.0530(17) Uani d . 1 C
H7 -0.2893 0.8902 0.0118 0.064 Uiso d R 1 H
C8 -0.1687(8) 0.8610(6) 0.1509(5) 0.0432(15) Uani d . 1 C
H8 -0.0861 0.8535 0.1244 0.052 Uiso d R 1 H
C9 -0.0505(6) 0.8233(6) 0.3345(5) 0.0327(13) Uani d . 1 C
N10 -0.3046(5) 0.8388(5) 0.4052(4) 0.0379(12) Uani d . 1 N
C11 -0.0496(6) 0.8179(5) 0.4481(5) 0.0325(14) Uani d . 1 C
C12 -0.1836(6) 0.8249(6) 0.4817(5) 0.0324(13) Uani d . 1 C
C13 -0.1713(6) 0.8449(6) 0.2622(5) 0.0352(14) Uani d . 1 C
C14 -0.2975(6) 0.8585(5) 0.3009(5) 0.0354(14) Uani d . 1 C
C15 0.0815(7) 0.8046(6) 0.2922(5) 0.0330(13) Uani d . 1 C
O16 0.0220(4) 0.6975(4) 0.1885(3) 0.0352(9) Uani d . 1 O
O17 0.2197(5) 0.8733(4) 0.3464(4) 0.0489(11) Uani d . 1 O
C18 0.1277(6) 0.6491(5) 0.1441(5) 0.0358(14) Uani d . 1 C
C19 0.1773(7) 0.6845(6) 0.0573(5) 0.0412(15) Uani d . 1 C
C20 0.2626(7) 0.6224(7) 0.0050(6) 0.0509(17) Uani d . 1 C
H20 0.2929 0.6445 -0.0558 0.061 Uiso d R 1 H
C21 0.2996(8) 0.5247(7) 0.0405(6) 0.0564(18) Uani d . 1 C
H21 0.3556 0.4812 0.0034 0.068 Uiso d R 1 H
C22 0.2557(7) 0.4911(6) 0.1291(6) 0.0520(17) Uani d . 1 C
H22 0.2828 0.4264 0.1543 0.062 Uiso d R 1 H
C23 0.1668(7) 0.5521(5) 0.1814(5) 0.0336(13) Uani d . 1 C
Br24 0.13315(9) 0.82219(8) 0.01180(7) 0.0651(3) Uani d . 1 Br
Br25 0.10690(10) 0.50960(8) 0.30427(7) 0.0682(3) Uani d . 1 Br
C26 -0.4511(7) 0.8276(8) 0.4348(6) 0.062(2) Uani d . 1 C
H26A -0.5274 0.8345 0.3720 0.092 Uiso calc PR 0.50 H
H26B -0.4253 0.9001 0.5093 0.092 Uiso calc PR 0.50 H
H26C -0.4950 0.7410 0.4421 0.092 Uiso calc PR 0.50 H
H26D -0.4377 0.8159 0.5103 0.092 Uiso calc PR 0.50 H
H26E -0.5399 0.7503 0.3729 0.092 Uiso calc PR 0.50 H
H26F -0.4701 0.9094 0.4402 0.092 Uiso calc PR 0.50 H
S27 0.47817(19) 0.74668(17) 0.74315(14) 0.0462(4) Uani d . 1 S
O28 0.4471(6) 0.7982(5) 0.6488(4) 0.0712(14) Uani d . 1 O
O29 0.6397(5) 0.7615(5) 0.7907(4) 0.0647(13) Uani d . 1 O
O30 0.4055(5) 0.7810(5) 0.8293(4) 0.0598(13) Uani d . 1 O
C31 0.3736(9) 0.5637(8) 0.6686(7) 0.067(2) Uani d . 1 C
F32 0.4299(7) 0.5121(5) 0.5889(5) 0.116(2) Uani d . 1 F
F33 0.3768(6) 0.5002(5) 0.7442(5) 0.0994(16) Uani d . 1 F
F34 0.2197(6) 0.5292(5) 0.6071(5) 0.0982(16) Uani d . 1 F
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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C11 120.4(5) ?
C2 C1 H1 119.5 ?
C11 C1 H1 120.1 ?
C1 C2 C3 120.7(6) ?
C1 C2 H2 120.0 ?
C3 C2 H2 119.2 ?
C4 C3 C2 120.3(6) ?
C4 C3 H3 119.2 ?
C2 C3 H3 120.6 ?
C3 C4 C12 120.6(5) ?
C3 C4 H4 119.7 ?
C12 C4 H4 119.7 ?
C6 C5 C14 119.1(6) ?
C6 C5 H5 121.4 ?
C14 C5 H5 119.5 ?
C5 C6 C7 121.8(6) ?
C5 C6 H6 117.9 ?
C7 C6 H6 120.1 ?
C8 C7 C6 121.2(6) ?
C8 C7 H7 120.0 ?
C6 C7 H7 118.5 ?
C7 C8 C13 119.7(6) ?
C7 C8 H8 120.9 ?
C13 C8 H8 119.4 ?
C13 C9 C11 121.1(5) ?
C13 C9 C15 120.0(5) ?
C11 C9 C15 119.0(5) ?
C12 N10 C14 122.6(4) ?
C12 N10 C26 118.3(5) ?
C14 N10 C26 119.0(5) ?
C1 C11 C9 123.6(5) ?
C1 C11 C12 118.8(5) ?
C9 C11 C12 117.6(5) ?
N10 C12 C4 121.2(5) ?
N10 C12 C11 119.6(5) ?
C4 C12 C11 119.3(5) ?
C9 C13 C14 119.7(5) ?
C9 C13 C8 122.1(5) ?
C14 C13 C8 118.2(5) ?
N10 C14 C5 121.1(5) ?
N10 C14 C13 118.8(5) ?
C5 C14 C13 120.1(6) ?
C9 C15 O16 110.1(5) yes
C9 C15 O17 124.5(5) yes
C15 O16 C18 118.7(4) yes
O16 C15 O17 125.4(5) yes
C19 C18 C23 120.1(5) ?
C19 C18 O16 121.8(5) ?
C23 C18 O16 117.7(5) ?
C20 C19 C18 120.4(6) ?
C20 C19 Br24 119.3(5) ?
C18 C19 Br24 120.3(4) ?
C19 C20 C21 119.6(6) ?
C19 C20 H20 120.1 ?
C21 C20 H20 120.2 ?
C22 C21 C20 120.9(6) ?
C22 C21 H21 119.8 ?
C20 C21 H21 119.4 ?
C21 C22 C23 119.9(6) ?
C21 C22 H22 120.8 ?
C23 C22 H22 119.3 ?
C18 C23 C22 119.1(5) ?
C18 C23 Br25 120.1(4) ?
C22 C23 Br25 120.8(5) ?
N10 C26 H26A 109.5 ?
N10 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
N10 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
N10 C26 H26D 109.5 ?
H26A C26 H26D 141.1 ?
H26B C26 H26D 56.3 ?
H26C C26 H26D 56.3 ?
N10 C26 H26E 109.5 ?
H26A C26 H26E 56.3 ?
H26B C26 H26E 141.1 ?
H26C C26 H26E 56.3 ?
H26D C26 H26E 109.5 ?
N10 C26 H26F 109.5 ?
H26A C26 H26F 56.3 ?
H26B C26 H26F 56.3 ?
H26C C26 H26F 141.1 ?
H26D C26 H26F 109.5 ?
H26E C26 H26F 109.5 ?
O30 S27 O29 115.9(3) ?
O30 S27 O28 114.1(3) ?
O29 S27 O28 114.5(3) ?
O30 S27 C31 103.3(3) ?
O29 S27 C31 102.5(3) ?
O28 S27 C31 104.2(4) ?
F32 C31 F33 108.5(7) ?
F32 C31 F34 105.1(7) ?
F33 C31 F34 106.6(7) ?
F32 C31 S27 112.2(6) ?
F33 C31 S27 112.4(6) ?
F34 C31 S27 111.6(6) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.355(8) ?
C1 C11 1.400(7) ?
C1 H1 0.9300 ?
C2 C3 1.419(8) ?
C2 H2 0.9306 ?
C3 C4 1.353(8) ?
C3 H3 0.9300 ?
C4 C12 1.397(8) ?
C4 H4 0.9300 ?
C5 C6 1.354(9) ?
C5 C14 1.409(8) ?
C5 H5 0.9300 ?
C6 C7 1.391(9) ?
C6 H6 0.9300 ?
C7 C8 1.345(8) ?
C7 H7 0.9300 ?
C8 C13 1.438(8) ?
C8 H8 0.9300 ?
C9 C13 1.393(7) ?
C9 C11 1.417(7) yes
C9 C15 1.505(8) yes
N10 C12 1.371(7) yes
N10 C14 1.376(7) ?
N10 C26 1.488(7) yes
C11 C12 1.436(7) ?
C13 C14 1.415(8) ?
C15 O16 1.336(7) yes
C15 O17 1.196(6) yes
O16 C18 1.413(6) yes
C18 C19 1.371(8) yes
C18 C23 1.385(8) ?
C19 C20 1.367(8) ?
C19 Br24 1.879(6) yes
C20 C21 1.373(9) ?
C20 H20 0.9300 ?
C21 C22 1.362(9) ?
C21 H21 0.9300 ?
C22 C23 1.389(8) ?
C22 H22 0.9300 ?
C23 Br25 1.865(5) ?
C26 H26A 0.9600 ?
C26 H26B 0.9600 ?
C26 H26C 0.9600 ?
C26 H26D 0.9600 ?
C26 H26E 0.9600 ?
C26 H26F 0.9600 ?
S27 O30 1.424(4) ?
S27 O29 1.433(5) ?
S27 O28 1.437(5) ?
S27 C31 1.805(8) ?
C31 F32 1.303(8) ?
C31 F33 1.311(9) ?
C31 F34 1.344(9) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
C7 H7 O29 1_555 1_555 1_454 0.93 2.52 3.362(8) 150 y
C20 H20 O30 1_555 1_555 1_554 0.93 2.52 3.413(8) 161 y
C22 H22 O29 1_555 1_555 2_666 0.93 2.59 3.523(9) 176 y
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
_geom_torsion_publ_flag
C11 C1 C2 C3 -0.6(9) ?
C1 C2 C3 C4 0.8(9) ?
C2 C3 C4 C12 -0.6(9) ?
C14 C5 C6 C7 1.0(10) ?
C5 C6 C7 C8 -2.0(11) ?
C6 C7 C8 C13 0.8(10) ?
C2 C1 C11 C9 -178.5(6) ?
C2 C1 C11 C12 0.3(8) ?
C13 C9 C11 C1 -176.4(5) ?
C15 C9 C11 C1 3.8(8) ?
C13 C9 C11 C12 4.7(8) ?
C15 C9 C11 C12 -175.1(5) ?
C14 N10 C12 C4 174.3(5) ?
C26 N10 C12 C4 -7.7(8) ?
C14 N10 C12 C11 -5.9(8) ?
C26 N10 C12 C11 172.2(5) ?
C3 C4 C12 N10 -179.8(6) ?
C3 C4 C12 C11 0.4(9) ?
C1 C11 C12 N10 180.0(5) ?
C9 C11 C12 N10 -1.1(8) ?
C1 C11 C12 C4 -0.2(8) ?
C9 C11 C12 C4 178.7(5) ?
C11 C9 C13 C14 -1.6(8) ?
C15 C9 C13 C14 178.2(5) ?
C11 C9 C13 C8 175.3(5) ?
C15 C9 C13 C8 -5.0(8) ?
C7 C8 C13 C9 -175.7(6) ?
C7 C8 C13 C14 1.2(9) ?
C12 N10 C14 C5 -170.9(5) ?
C26 N10 C14 C5 11.1(8) ?
C12 N10 C14 C13 9.1(8) ?
C26 N10 C14 C13 -168.9(5) ?
C6 C5 C14 N10 -178.9(6) ?
C6 C5 C14 C13 1.1(9) ?
C9 C13 C14 N10 -5.2(8) ?
C8 C13 C14 N10 177.8(5) ?
C9 C13 C14 C5 174.8(5) ?
C8 C13 C14 C5 -2.2(8) ?
C13 C9 C15 O17 123.5(6) ?
C13 C9 C15 O16 -58.9(6) ?
C11 C9 C15 O16 120.9(5) ?
O17 C15 O16 C18 8.0(8) ?
C9 C15 O16 C18 -169.6(5) yes
C11 C9 C15 O17 -56.7(8) yes
C15 O16 C18 C19 -98.7(6) yes
C15 O16 C18 C23 88.3(6) ?
C23 C18 C19 C20 1.4(9) ?
O16 C18 C19 C20 -171.4(5) ?
C23 C18 C19 Br24 -177.0(4) ?
O16 C18 C19 Br24 10.2(8) yes
C18 C19 C20 C21 -0.5(9) ?
Br24 C19 C20 C21 178.0(5) ?
C19 C20 C21 C22 -1.6(10) ?
C20 C21 C22 C23 2.6(10) ?
C19 C18 C23 C22 -0.4(9) ?
O16 C18 C23 C22 172.8(5) ?
C19 C18 C23 Br25 177.3(4) ?
O16 C18 C23 Br25 -9.6(7) ?
C21 C22 C23 C18 -1.6(9) ?
C21 C22 C23 Br25 -179.3(5) ?
O30 S27 C31 F32 -177.0(6) ?
O29 S27 C31 F32 -56.2(7) ?
O28 S27 C31 F32 63.5(7) ?
O30 S27 C31 F33 -54.4(6) ?
O29 S27 C31 F33 66.4(6) ?
O28 S27 C31 F33 -174.0(5) ?
O30 S27 C31 F34 65.3(6) ?
O29 S27 C31 F34 -173.9(6) ?
O28 S27 C31 F34 -54.2(6) ?
