#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/79/2207954.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_2207954
loop_
_publ_author_name
'Artur Sikorski'
'Karol Krzymiński'
'Agata Białońska'
'Tadeusz Lis'
'Jerzy Błażejowski'
_publ_section_title
;
 10-Methyl-9-(2-methylphenoxycarbonyl)acridinium
 trifluoromethanesulfonate
;
_journal_coeditor_code           AC6227
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o822
_journal_page_last               o824
_journal_paper_doi               10.1107/S1600536806002340
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H18 N O2 + , C F3 O3 S -'
_chemical_formula_moiety         'C22 H18 N O2 + , C F3 O3 S -'
_chemical_formula_sum            'C23 H18 F3 N O5 S'
_chemical_formula_weight         477.45
_chemical_name_systematic
;
10-Methyl-9-(2-methylphenoxycarbonyl)acridinium 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                80.35(3)
_cell_angle_beta                 87.87(3)
_cell_angle_gamma                80.03(3)
_cell_formula_units_Z            2
_cell_length_a                   9.160(2)
_cell_length_b                   10.558(2)
_cell_length_c                   11.060(2)
_cell_measurement_reflns_used    5975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.12
_cell_volume                     1038.5(4)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Kuma KM-4-CCD κ-geometry'
_diffrn_measurement_method       ω
_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  0.034
_diffrn_reflns_av_sigmaI/netI    0.064
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6626
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.22
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.062
_refine_ls_R_factor_gt           0.034
_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)+(0.0245P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.063
_refine_ls_wR_factor_ref         0.067
_reflns_number_gt                2437
_reflns_number_total             3564
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6227.cif
_cod_data_source_block           I
_cod_database_code               2207954
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 0.1863(2) 0.99908(18) 0.03961(19) 0.0171(5) Uani d . 1 C
H1 0.1905 1.0789 0.0670 0.020 Uiso calc R 1 H
C2 0.1941(2) 0.99397(18) -0.08144(19) 0.0173(5) Uani d . 1 C
H2 0.2035 1.0700 -0.1388 0.021 Uiso calc R 1 H
C3 0.1884(2) 0.87546(18) -0.12311(19) 0.0196(5) Uani d . 1 C
H3 0.1943 0.8730 -0.2086 0.024 Uiso calc R 1 H
C4 0.1746(2) 0.76458(19) -0.04336(18) 0.0184(5) Uani d . 1 C
H4 0.1700 0.6863 -0.0736 0.022 Uiso calc R 1 H
C5 0.1632(2) 0.53996(19) 0.37890(19) 0.0202(5) Uani d . 1 C
H5 0.1727 0.4583 0.3515 0.024 Uiso calc R 1 H
C6 0.1566(2) 0.5451(2) 0.5011(2) 0.0233(5) Uani d . 1 C
H6 0.1648 0.4660 0.5578 0.028 Uiso calc R 1 H
C7 0.1378(2) 0.66492(19) 0.5464(2) 0.0232(5) Uani d . 1 C
H7 0.1268 0.6667 0.6319 0.028 Uiso calc R 1 H
C8 0.1359(2) 0.77690(19) 0.46552(18) 0.0197(5) Uani d . 1 C
H8 0.1258 0.8573 0.4954 0.024 Uiso calc R 1 H
C9 0.1629(2) 0.88846(18) 0.25279(18) 0.0154(5) Uani d . 1 C
N10 0.16051(16) 0.65533(14) 0.16876(15) 0.0157(4) Uani d . 1 N
C11 0.1716(2) 0.88606(18) 0.12721(18) 0.0149(5) Uani d . 1 C
C12 0.1671(2) 0.76625(18) 0.08407(18) 0.0140(5) Uani d . 1 C
C13 0.1488(2) 0.77680(18) 0.33759(18) 0.0157(5) Uani d . 1 C
C14 0.1560(2) 0.65632(18) 0.29237(19) 0.0170(5) Uani d . 1 C
C15 0.1769(2) 1.01267(19) 0.29875(17) 0.0166(5) Uani d . 1 C
O16 0.32269(14) 1.01472(12) 0.30869(12) 0.0194(3) Uani d . 1 O
O17 0.07683(15) 1.09417(13) 0.32196(13) 0.0241(4) Uani d . 1 O
C18 0.3684(2) 1.12662(18) 0.34204(19) 0.0192(5) Uani d . 1 C
C19 0.3583(2) 1.14740(19) 0.46204(19) 0.0202(5) Uani d . 1 C
C20 0.4221(2) 1.25166(19) 0.4882(2) 0.0250(5) Uani d . 1 C
H20 0.4174 1.2705 0.5694 0.030 Uiso calc R 1 H
C21 0.4915(2) 1.3270(2) 0.3972(2) 0.0260(5) Uani d . 1 C
H21 0.5342 1.3966 0.4171 0.031 Uiso calc R 1 H
C22 0.4999(2) 1.30342(19) 0.2782(2) 0.0254(5) Uani d . 1 C
H22 0.5478 1.3563 0.2167 0.031 Uiso calc R 1 H
C23 0.4377(2) 1.20130(19) 0.2490(2) 0.0230(5) Uani d . 1 C
H23 0.4425 1.1830 0.1676 0.028 Uiso calc R 1 H
C24 0.2861(2) 1.06340(19) 0.56189(19) 0.0263(5) Uani d . 1 C
H24A 0.3143 1.0790 0.6420 0.040 Uiso calc R 1 H
H24B 0.3189 0.9714 0.5552 0.040 Uiso calc R 1 H
H24C 0.1782 1.0850 0.5535 0.040 Uiso calc R 1 H
C25 0.1626(2) 0.53008(17) 0.12404(19) 0.0220(5) Uani d . 1 C
H25A 0.0938 0.4806 0.1734 0.033 Uiso calc R 1 H
H25B 0.2630 0.4793 0.1312 0.033 Uiso calc R 1 H
H25C 0.1323 0.5476 0.0380 0.033 Uiso calc R 1 H
S26 0.23257(6) 0.36221(5) 0.84983(5) 0.01791(14) Uani d . 1 S
O27 0.17644(15) 0.31158(12) 0.96862(12) 0.0213(3) Uani d . 1 O
O28 0.21171(15) 0.50317(12) 0.82054(12) 0.0229(4) Uani d . 1 O
O29 0.20178(14) 0.29779(12) 0.75065(12) 0.0225(4) Uani d . 1 O
C30 0.4331(2) 0.3167(2) 0.8671(2) 0.0231(5) Uani d . 1 C
F31 0.47393(13) 0.18848(11) 0.89992(12) 0.0391(4) Uani d . 1 F
F32 0.48232(13) 0.37370(12) 0.95377(11) 0.0359(3) Uani d . 1 F
F33 0.50550(13) 0.35291(12) 0.76367(11) 0.0342(3) 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'
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 120.89(18) ?
C2 C1 H1 119.6 ?
C11 C1 H1 119.6 ?
C1 C2 C3 119.98(18) ?
C1 C2 H2 120.0 ?
C3 C2 H2 120.0 ?
C4 C3 C2 121.5(2) ?
C4 C3 H3 119.2 ?
C2 C3 H3 119.2 ?
C3 C4 C12 119.97(18) ?
C3 C4 H4 120.0 ?
C12 C4 H4 120.0 ?
C6 C5 C14 120.10(19) ?
C6 C5 H5 119.9 ?
C14 C5 H5 119.9 ?
C5 C6 C7 122.01(19) ?
C5 C6 H6 119.0 ?
C7 C6 H6 119.0 ?
C8 C7 C6 118.8(2) ?
C8 C7 H7 120.6 ?
C6 C7 H7 120.6 ?
C7 C8 C13 121.51(19) ?
C7 C8 H8 119.2 ?
C13 C8 H8 119.2 ?
C11 C9 C13 121.52(17) ?
C11 C9 C15 119.13(16) ?
C13 C9 C15 119.27(18) ?
C14 N10 C12 122.27(16) ?
C14 N10 C25 118.96(15) ?
C12 N10 C25 118.75(16) ?
C9 C11 C1 122.17(17) ?
C9 C11 C12 119.15(17) ?
C1 C11 C12 118.68(18) ?
N10 C12 C4 122.19(17) ?
N10 C12 C11 118.83(17) ?
C4 C12 C11 118.94(17) ?
C9 C13 C8 122.84(18) ?
C9 C13 C14 117.96(18) ?
C8 C13 C14 119.11(17) ?
N10 C14 C5 121.85(17) ?
N10 C14 C13 119.95(17) ?
C5 C14 C13 118.17(19) ?
O17 C15 O16 126.38(18) ?
C9 C15 O16 107.48(17) yes
C9 C15 O17 126.14(18) yes
C15 O16 C18 119.35(15) ?
C19 C18 C23 123.81(19) ?
C19 C18 O16 120.66(17) ?
C23 C18 O16 115.10(18) ?
C18 C19 C20 116.30(19) ?
C18 C19 C24 122.96(18) ?
C20 C19 C24 120.74(19) ?
C21 C20 C19 120.8(2) ?
C21 C20 H20 119.6 ?
C19 C20 H20 119.6 ?
C22 C21 C20 121.4(2) ?
C22 C21 H21 119.3 ?
C20 C21 H21 119.3 ?
C21 C22 C23 119.3(2) ?
C21 C22 H22 120.3 ?
C23 C22 H22 120.3 ?
C22 C23 C18 118.3(2) ?
C22 C23 H23 120.8 ?
C18 C23 H23 120.8 ?
C19 C24 H24A 109.5 ?
C19 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
C19 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
N10 C25 H25A 109.5 ?
N10 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
N10 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
O29 S26 O27 115.28(8) ?
O29 S26 O28 114.83(8) ?
O27 S26 O28 114.98(8) ?
O29 S26 C30 103.24(9) ?
O27 S26 C30 103.17(9) ?
O28 S26 C30 102.86(9) ?
F31 C30 F33 107.69(17) ?
F31 C30 F32 107.10(17) ?
F33 C30 F32 106.79(15) ?
F31 C30 S26 111.75(13) ?
F33 C30 S26 112.04(14) ?
F32 C30 S26 111.20(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.348(3) ?
C1 C11 1.428(2) ?
C1 H1 0.9500 ?
C2 C3 1.414(3) ?
C2 H2 0.9500 ?
C3 C4 1.364(3) ?
C3 H3 0.9500 ?
C4 C12 1.411(3) ?
C4 H4 0.9500 ?
C5 C6 1.360(3) ?
C5 C14 1.418(3) ?
C5 H5 0.9500 ?
C6 C7 1.418(3) ?
C6 H6 0.9500 ?
C7 C8 1.356(3) ?
C7 H7 0.9500 ?
C8 C13 1.416(3) ?
C8 H8 0.9500 ?
C9 C11 1.392(3) yes
C9 C13 1.400(2) ?
C9 C15 1.511(3) yes
N10 C14 1.368(2) ?
N10 C12 1.380(2) yes
N10 C25 1.484(2) yes
C11 C12 1.432(2) ?
C13 C14 1.433(3) ?
C15 O16 1.348(2) yes
C15 O17 1.196(2) yes
O16 C18 1.427(2) yes
C18 C19 1.378(3) yes
C18 C23 1.392(3) ?
C19 C20 1.407(3) ?
C19 C24 1.504(3) yes
C20 C21 1.382(3) ?
C20 H20 0.9500 ?
C21 C22 1.376(3) ?
C21 H21 0.9500 ?
C22 C23 1.391(3) ?
C22 H22 0.9500 ?
C23 H23 0.9500 ?
C24 H24A 0.9800 ?
C24 H24B 0.9800 ?
C24 H24C 0.9800 ?
C25 H25A 0.9800 ?
C25 H25B 0.9800 ?
C25 H25C 0.9800 ?
S26 O29 1.4438(13) ?
S26 O27 1.4442(13) ?
S26 O28 1.4494(13) ?
S26 C30 1.825(2) ?
C30 F31 1.332(2) ?
C30 F33 1.334(2) ?
C30 F32 1.343(2) ?
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
C1 H1 O27 1_564 0.95 2.50 3.247(2) 136 y
C2 H2 O29 1_564 0.95 2.50 3.435(2) 166 y
C4 H4 O28 1_554 0.95 2.39 3.322(2) 165 y
C6 H6 O29 . 0.95 2.53 3.450(3) 163 y
C7 H7 O28 . 0.95 2.53 3.253(3) 133 y
C25 H25C O28 1_554 0.98 2.58 3.423(3) 144 y
C5 H5 Cg4 1_545 0.95 3.08 3.773(2) 132 y
C6 H6 Cg3 2_566 0.95 3.36 3.822(2) 112 y
C21 H21 Cg3 2_676 0.95 3.38 3.954(2) 121 y
C24 H24B Cg4 2_676 0.98 2.87 3.649(2) 137 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 -0.2(3) ?
C1 C2 C3 C4 0.2(3) ?
C2 C3 C4 C12 -0.6(3) ?
C14 C5 C6 C7 2.0(3) ?
C5 C6 C7 C8 -4.3(3) ?
C6 C7 C8 C13 1.5(3) ?
C13 C9 C11 C1 -179.90(18) ?
C15 C9 C11 C1 -3.1(3) ?
C13 C9 C11 C12 -0.5(3) ?
C15 C9 C11 C12 176.33(17) ?
C2 C1 C11 C9 -179.84(19) ?
C2 C1 C11 C12 0.7(3) ?
C14 N10 C12 C4 178.80(18) ?
C25 N10 C12 C4 0.5(3) ?
C14 N10 C12 C11 1.0(3) ?
C25 N10 C12 C11 -177.33(16) ?
C3 C4 C12 N10 -176.74(17) ?
C3 C4 C12 C11 1.1(3) ?
C9 C11 C12 N10 -2.7(3) ?
C1 C11 C12 N10 176.79(16) ?
C9 C11 C12 C4 179.40(18) ?
C1 C11 C12 C4 -1.1(3) ?
C11 C9 C13 C8 -178.38(18) ?
C15 C9 C13 C8 4.8(3) ?
C11 C9 C13 C14 5.1(3) ?
C15 C9 C13 C14 -171.67(17) ?
C7 C8 C13 C9 -173.09(18) ?
C7 C8 C13 C14 3.4(3) ?
C12 N10 C14 C5 -173.96(17) ?
C25 N10 C14 C5 4.3(3) ?
C12 N10 C14 C13 3.8(3) ?
C25 N10 C14 C13 -177.87(16) ?
C6 C5 C14 N10 -179.23(18) ?
C6 C5 C14 C13 2.9(3) ?
C9 C13 C14 N10 -6.8(3) ?
C8 C13 C14 N10 176.55(17) ?
C9 C13 C14 C5 171.09(17) ?
C8 C13 C14 C5 -5.6(3) ?
C11 C9 C15 O17 95.4(2) yes
C13 C9 C15 O17 -87.7(2) ?
C11 C9 C15 O16 -84.6(2) ?
C13 C9 C15 O16 92.3(2) ?
O17 C15 O16 C18 -4.5(3) ?
C9 C15 O16 C18 175.48(15) ?
C15 O16 C18 C19 77.0(2) yes
C15 O16 C18 C23 -110.11(19) ?
C23 C18 C19 C20 0.5(3) ?
O16 C18 C19 C20 172.72(17) ?
C23 C18 C19 C24 -178.42(19) ?
O16 C18 C19 C24 -6.2(3) ?
C18 C19 C20 C21 -0.5(3) ?
C24 C19 C20 C21 178.47(19) ?
C19 C20 C21 C22 0.3(3) ?
C20 C21 C22 C23 -0.2(3) ?
C21 C22 C23 C18 0.2(3) ?
C19 C18 C23 C22 -0.4(3) ?
O16 C18 C23 C22 -172.97(17) ?
O29 S26 C30 F31 -62.96(16) ?
O27 S26 C30 F31 57.41(16) ?
O28 S26 C30 F31 177.29(14) ?
O29 S26 C30 F33 57.99(15) ?
O27 S26 C30 F33 178.36(13) ?
O28 S26 C30 F33 -61.75(15) ?
O29 S26 C30 F32 177.41(13) ?
O27 S26 C30 F32 -62.22(15) ?
O28 S26 C30 F32 57.66(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126624
