#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/81/2228126.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228126
loop_
_publ_author_name
'Trzybiński, Damian'
'Krzymiński, Karol'
'Błażejowski, Jerzy'
_publ_section_title
;
 9-(4-Chlorophenoxycarbonyl)-10-methylacridinium
 trifluoromethanesulfonate
;
_journal_coeditor_code           XU5039
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2771
_journal_page_last               o2772
_journal_paper_doi               10.1107/S1600536810039541
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H15 Cl N O2 +, C F3 S O3 -'
_chemical_formula_moiety         'C21 H15 Cl N O2, C F3 S O3'
_chemical_formula_sum            'C22 H15 Cl F3 N O5 S'
_chemical_formula_weight         497.87
_chemical_name_systematic
;
9-(4-Chlorophenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 106.577(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3025(11)
_cell_length_b                   8.6750(9)
_cell_length_c                   19.6191(18)
_cell_measurement_reflns_used    1665
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0855
_cell_measurement_theta_min      3.0379
_cell_volume                     2169.9(4)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection
'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97  (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4002
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhanced (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11162
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0495
_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)+(0.0386P)²+1.4339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                2679
_reflns_number_total             3777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5039.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228126
_cod_database_fobs_code          2228126
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.6412(3) 0.7757(4) 0.51159(16) 0.0551(8) Uani d . 1 . .
H H1 0.5968 0.8280 0.5327 0.066 Uiso calc R 1 . .
C C2 0.7459(3) 0.7893(4) 0.53941(18) 0.0655(9) Uani d . 1 . .
H H2 0.7736 0.8503 0.5794 0.079 Uiso calc R 1 . .
C C3 0.8127(3) 0.7105(4) 0.50748(19) 0.0642(9) Uani d . 1 . .
H H3 0.8848 0.7193 0.5274 0.077 Uiso calc R 1 . .
C C4 0.7761(2) 0.6220(4) 0.44874(17) 0.0545(8) Uani d . 1 . .
H H4 0.8226 0.5731 0.4284 0.065 Uiso calc R 1 . .
C C5 0.4792(3) 0.3888(4) 0.27537(17) 0.0610(9) Uani d . 1 . .
H H5 0.5241 0.3355 0.2551 0.073 Uiso calc R 1 . .
C C6 0.3742(3) 0.3699(5) 0.2497(2) 0.0827(12) Uani d . 1 . .
H H6 0.3480 0.3034 0.2116 0.099 Uiso calc R 1 . .
C C7 0.3035(3) 0.4472(5) 0.2787(2) 0.0811(12) Uani d . 1 . .
H H7 0.2316 0.4327 0.2597 0.097 Uiso calc R 1 . .
C C8 0.3403(2) 0.5423(4) 0.33414(19) 0.0610(9) Uani d . 1 . .
H H8 0.2933 0.5927 0.3536 0.073 Uiso calc R 1 . .
C C9 0.4901(2) 0.6658(3) 0.42070(14) 0.0407(7) Uani d . 1 . .
N N10 0.62580(17) 0.5155(3) 0.35967(12) 0.0408(5) Uani d . 1 . .
C C11 0.5976(2) 0.6831(3) 0.45086(14) 0.0408(7) Uani d . 1 . .
C C12 0.6666(2) 0.6045(3) 0.41855(15) 0.0416(7) Uani d . 1 . .
C C13 0.4494(2) 0.5676(3) 0.36378(15) 0.0426(7) Uani d . 1 . .
C C14 0.5202(2) 0.4893(3) 0.33286(14) 0.0421(7) Uani d . 1 . .
C C15 0.4160(2) 0.7658(3) 0.44662(15) 0.0451(7) Uani d . 1 . .
O O16 0.39162(15) 0.7040(2) 0.50208(10) 0.0497(5) Uani d . 1 . .
O O17 0.3831(2) 0.8846(3) 0.41934(13) 0.0785(8) Uani d . 1 . .
C C18 0.3180(2) 0.7867(3) 0.52827(14) 0.0410(7) Uani d . 1 . .
C C19 0.2135(2) 0.7596(4) 0.49788(15) 0.0503(8) Uani d . 1 . .
H H19 0.1910 0.6928 0.4594 0.060 Uiso calc R 1 . .
C C20 0.1421(2) 0.8339(4) 0.52579(16) 0.0566(8) Uani d . 1 . .
H H20 0.0706 0.8176 0.5063 0.068 Uiso calc R 1 . .
C C21 0.1776(3) 0.9314(4) 0.58220(15) 0.0535(8) Uani d . 1 . .
C C22 0.2823(3) 0.9565(4) 0.61275(15) 0.0558(8) Uani d . 1 . .
H H22 0.3049 1.0220 0.6516 0.067 Uiso calc R 1 . .
C C23 0.3544(2) 0.8829(3) 0.58496(15) 0.0484(7) Uani d . 1 . .
H H23 0.4259 0.8987 0.6045 0.058 Uiso calc R 1 . .
Cl Cl24 0.08737(9) 1.02661(14) 0.61618(5) 0.0951(4) Uani d . 1 . .
C C25 0.6984(2) 0.4487(4) 0.32249(17) 0.0568(8) Uani d . 1 . .
H H25A 0.6590 0.4126 0.2763 0.085 Uiso calc R 1 . .
H H25B 0.7360 0.3641 0.3497 0.085 Uiso calc R 1 . .
H H25C 0.7473 0.5262 0.3173 0.085 Uiso calc R 1 . .
S S26 0.99146(6) 0.51449(9) 0.33370(4) 0.0456(2) Uani d . 1 . .
O O27 0.91136(17) 0.6102(2) 0.28913(11) 0.0578(6) Uani d . 1 . .
O O28 0.96649(17) 0.4501(3) 0.39381(11) 0.0709(7) Uani d . 1 . .
O O29 1.09667(17) 0.5708(3) 0.34719(12) 0.0704(7) Uani d . 1 . .
C C30 0.9908(3) 0.3493(4) 0.27794(18) 0.0641(9) Uani d . 1 . .
F F31 0.89748(18) 0.2801(2) 0.25860(13) 0.0971(7) Uani d . 1 . .
F F32 1.01300(19) 0.3885(3) 0.21805(11) 0.0974(8) Uani d . 1 . .
F F33 1.06074(19) 0.2433(3) 0.30961(12) 0.0989(8) Uani d . 1 . .
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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C11 . . 121.2(3) ?
C2 C1 H1 . . 119.4 ?
C11 C1 H1 . . 119.4 ?
C1 C2 C3 . . 119.3(3) ?
C1 C2 H2 . . 120.4 ?
C3 C2 H2 . . 120.4 ?
C4 C3 C2 . . 122.5(3) ?
C4 C3 H3 . . 118.8 ?
C2 C3 H3 . . 118.8 ?
C3 C4 C12 . . 119.6(3) ?
C3 C4 H4 . . 120.2 ?
C12 C4 H4 . . 120.2 ?
C6 C5 C14 . . 119.7(3) ?
C6 C5 H5 . . 120.1 ?
C14 C5 H5 . . 120.1 ?
C5 C6 C7 . . 122.2(3) ?
C5 C6 H6 . . 118.9 ?
C7 C6 H6 . . 118.9 ?
C8 C7 C6 . . 119.4(3) ?
C8 C7 H7 . . 120.3 ?
C6 C7 H7 . . 120.3 ?
C7 C8 C13 . . 121.5(3) ?
C7 C8 H8 . . 119.3 ?
C13 C8 H8 . . 119.3 ?
C13 C9 C11 . . 121.7(2) ?
C13 C9 C15 . . 118.9(3) ?
C11 C9 C15 . . 119.1(3) ?
C12 N10 C14 . . 122.3(2) ?
C12 N10 C25 . . 118.6(2) ?
C14 N10 C25 . . 119.1(2) ?
C9 C11 C1 . . 122.9(3) ?
C9 C11 C12 . . 118.2(3) ?
C1 C11 C12 . . 118.9(3) ?
N10 C12 C4 . . 121.8(3) ?
N10 C12 C11 . . 119.6(3) ?
C4 C12 C11 . . 118.6(3) ?
C9 C13 C8 . . 122.9(3) ?
C9 C13 C14 . . 118.8(3) ?
C8 C13 C14 . . 118.3(3) ?
N10 C14 C5 . . 122.0(2) ?
N10 C14 C13 . . 119.1(2) ?
C5 C14 C13 . . 118.9(3) ?
O17 C15 O16 . . 125.0(3) ?
O17 C15 C9 . . 122.7(3) ?
O16 C15 C9 . . 112.2(2) ?
C15 O16 C18 . . 116.4(2) ?
C23 C18 C19 . . 122.7(3) ?
C23 C18 O16 . . 118.8(3) ?
C19 C18 O16 . . 118.3(2) ?
C18 C19 C20 . . 118.3(3) ?
C18 C19 H19 . . 120.8 ?
C20 C19 H19 . . 120.8 ?
C21 C20 C19 . . 119.5(3) ?
C21 C20 H20 . . 120.3 ?
C19 C20 H20 . . 120.3 ?
C20 C21 C22 . . 121.8(3) ?
C20 C21 Cl24 . . 119.2(3) ?
C22 C21 Cl24 . . 119.0(2) ?
C21 C22 C23 . . 119.1(3) ?
C21 C22 H22 . . 120.4 ?
C23 C22 H22 . . 120.4 ?
C18 C23 C22 . . 118.6(3) ?
C18 C23 H23 . . 120.7 ?
C22 C23 H23 . . 120.7 ?
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 ?
O28 S26 O29 . . 115.20(14) ?
O28 S26 O27 . . 115.00(13) ?
O29 S26 O27 . . 115.57(14) ?
O28 S26 C30 . . 103.23(17) ?
O29 S26 C30 . . 102.62(16) ?
O27 S26 C30 . . 102.48(14) ?
F33 C30 F31 . . 107.0(3) ?
F33 C30 F32 . . 106.6(3) ?
F31 C30 F32 . . 106.6(3) ?
F33 C30 S26 . . 112.6(2) ?
F31 C30 S26 . . 112.0(2) ?
F32 C30 S26 . . 111.6(3) ?
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 . 1.349(4) ?
C1 C11 . 1.417(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.402(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.354(5) ?
C3 H3 . 0.9300 ?
C4 C12 . 1.415(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.353(5) ?
C5 C14 . 1.407(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.401(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.341(5) ?
C7 H7 . 0.9300 ?
C8 C13 . 1.418(4) ?
C8 H8 . 0.9300 ?
C9 C13 . 1.386(4) ?
C9 C11 . 1.391(4) ?
C9 C15 . 1.506(4) ?
N10 C12 . 1.367(4) ?
N10 C14 . 1.372(3) ?
N10 C25 . 1.485(3) ?
C11 C12 . 1.429(4) ?
C13 C14 . 1.428(4) ?
C15 O17 . 1.186(3) ?
C15 O16 . 1.334(3) ?
O16 C18 . 1.423(3) ?
C18 C23 . 1.364(4) ?
C18 C19 . 1.367(4) ?
C19 C20 . 1.384(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.366(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.368(4) ?
C21 Cl24 . 1.739(3) ?
C22 C23 . 1.386(4) ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
S26 O28 . 1.427(2) ?
S26 O29 . 1.434(2) ?
S26 O27 . 1.434(2) ?
S26 C30 . 1.801(4) ?
C30 F33 . 1.330(4) ?
C30 F31 . 1.333(4) ?
C30 F32 . 1.335(4) ?
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
C3 H3 O28 1_555 1_555 3_766 0.93 2.59 3.328(5) 136 y
C4 H4 O28 1_555 1_555 1_555 0.93 2.45 3.370(4) 171 y
C5 H5 O27 1_555 1_555 2_645 0.93 2.39 3.258(4) 154 y
C6 H6 O29 1_555 1_555 2_645 0.93 2.54 3.304(5) 140 y
C8 H8 O29 1_555 1_555 1_455 0.93 2.59 3.332(4) 137 y
C19 H19 O29 1_555 1_555 1_455 0.93 2.44 3.349(4) 165 y
C25 H25C O27 1_555 1_555 1_555 0.96 2.51 3.387(4) 152 y
C25 H25B Cg4 1_555 1_555 3_666 0.96 2.65 3.519(4) 151 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_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 C3 . . . . 0.1(5) ?
C1 C2 C3 C4 . . . . 0.9(5) ?
C2 C3 C4 C12 . . . . -1.3(5) ?
C14 C5 C6 C7 . . . . -0.3(6) ?
C5 C6 C7 C8 . . . . -0.6(7) ?
C6 C7 C8 C13 . . . . 0.6(6) ?
C13 C9 C11 C1 . . . . -176.2(3) ?
C15 C9 C11 C1 . . . . 8.8(4) ?
C13 C9 C11 C12 . . . . 4.3(4) ?
C15 C9 C11 C12 . . . . -170.7(2) ?
C2 C1 C11 C9 . . . . 179.9(3) ?
C2 C1 C11 C12 . . . . -0.6(4) ?
C14 N10 C12 C4 . . . . 175.5(2) ?
C25 N10 C12 C4 . . . . -6.3(4) ?
C14 N10 C12 C11 . . . . -4.7(4) ?
C25 N10 C12 C11 . . . . 173.5(2) ?
C3 C4 C12 N10 . . . . -179.4(3) ?
C3 C4 C12 C11 . . . . 0.8(4) ?
C9 C11 C12 N10 . . . . -0.1(4) ?
C1 C11 C12 N10 . . . . -179.6(2) ?
C9 C11 C12 C4 . . . . 179.7(2) ?
C1 C11 C12 C4 . . . . 0.2(4) ?
C11 C9 C13 C8 . . . . 177.0(3) ?
C15 C9 C13 C8 . . . . -8.0(4) ?
C11 C9 C13 C14 . . . . -3.8(4) ?
C15 C9 C13 C14 . . . . 171.2(2) ?
C7 C8 C13 C9 . . . . 179.5(3) ?
C7 C8 C13 C14 . . . . 0.3(5) ?
C12 N10 C14 C5 . . . . -175.4(3) ?
C25 N10 C14 C5 . . . . 6.4(4) ?
C12 N10 C14 C13 . . . . 5.2(4) ?
C25 N10 C14 C13 . . . . -173.0(2) ?
C6 C5 C14 N10 . . . . -178.3(3) ?
C6 C5 C14 C13 . . . . 1.1(5) ?
C9 C13 C14 N10 . . . . -1.0(4) ?
C8 C13 C14 N10 . . . . 178.3(3) ?
C9 C13 C14 C5 . . . . 179.6(3) ?
C8 C13 C14 C5 . . . . -1.1(4) ?
C13 C9 C15 O17 . . . . -82.2(4) ?
C11 C9 C15 O17 . . . . 92.9(4) ?
C13 C9 C15 O16 . . . . 96.9(3) ?
C11 C9 C15 O16 . . . . -88.0(3) ?
O17 C15 O16 C18 . . . . 1.9(4) ?
C9 C15 O16 C18 . . . . -177.1(2) ?
C15 O16 C18 C23 . . . . -96.8(3) ?
C15 O16 C18 C19 . . . . 86.8(3) ?
C23 C18 C19 C20 . . . . 0.4(4) ?
O16 C18 C19 C20 . . . . 176.7(3) ?
C18 C19 C20 C21 . . . . 0.1(5) ?
C19 C20 C21 C22 . . . . -0.9(5) ?
C19 C20 C21 Cl24 . . . . 179.1(2) ?
C20 C21 C22 C23 . . . . 1.1(5) ?
Cl24 C21 C22 C23 . . . . -178.9(2) ?
C19 C18 C23 C22 . . . . -0.2(4) ?
O16 C18 C23 C22 . . . . -176.4(2) ?
C21 C22 C23 C18 . . . . -0.6(4) ?
O28 S26 C30 F33 . . . . -60.1(3) ?
O29 S26 C30 F33 . . . . 60.0(3) ?
O27 S26 C30 F33 . . . . -179.9(3) ?
O28 S26 C30 F31 . . . . 60.5(3) ?
O29 S26 C30 F31 . . . . -179.4(2) ?
O27 S26 C30 F31 . . . . -59.2(3) ?
O28 S26 C30 F32 . . . . 180.0(2) ?
O29 S26 C30 F32 . . . . -60.0(3) ?
O27 S26 C30 F32 . . . . 60.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656318
