Literature DB >> 21582497

9-Chloro-2,4-dimethoxy-acridinium trifluoro-methane-sulfonate.

Beata Zadykowicz1, Karol Krzymiński, Damian Trzybiński, Artur Sikorski, Jerzy Błażejowski.   

Abstract

In the mol-ecular structure of the title compound, C(15)H(13)ClNO(2) (+)·CF(3)SO(3) (-), the n class="Chemical">meth-oxy groups are nearly coplanar with the acridine ring system, making dihedral angles of 0.4 (2) and 5.1 (2)°. Multidirectional π-π contacts between acridine units are observed in the crystal structure. N-H⋯O and C-H⋯O hydrogen bonds link cations and anions, forming a layer structure.

Entities:  

Year:  2009        PMID： 21582497      PMCID： PMC2968865          DOI： 10.1107/S1600536809008551

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background, see: Acheson (1973 ▶); Demeunynck et al. (2001 ▶); Wróblewska et al. (2004 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Achari & Neidle (1977 ▶); n class="Chemical">Neidle (1982 ▶); Ning et al. (1976 ▶); Ojida et al. (2006 ▶); Rimmer et al. (2000 ▶); Toma et al. (1993 ▶). For inter­molecular inter­actions, see: Aakeröy et al. (1992 ▶); Bianchi et al. (2004 ▶); Hunter et al. (2001 ▶); Steiner (1999 ▶). For the synthesis, see: Acheson (1973 ▶); Sato (1996 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C15H13ClNO2 +·CF3SO3 − M = 423.79 Monoclinic, a = 11.0502 (9) Å b = 23.110 (2) Å c = 7.1435 (8) Å β = 108.214 (11)° V = 1732.8 (3) Å3 Z = 4 Mo Kα radiation μ = 0.40 mm−1 T = 295 K 0.60 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.782, T max = 0.959 12548 measured reflections 3072 independent reflections 1932 reflections with I > 2σ(I) R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.179 S = 1.06 3072 reflections 246 parameters H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.28 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data n class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008551/xu2477sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008551/xu2477Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H13ClNO2+·CF3SO3−F(000) = 864
Mr = 423.79Dx = 1.625 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5776 reflections
a = 11.0502 (9) Åθ = 3.0–29.2°
b = 23.110 (2) ŵ = 0.40 mm−1
c = 7.1435 (8) ÅT = 295 K
β = 108.214 (11)°Plate, purple
V = 1732.8 (3) Å30.60 × 0.20 × 0.10 mm
Z = 4
Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer3072 independent reflections
Radiation source: Enhance (Mo) X-ray Source1932 reflections with I > 2σ(I)
graphiteRint = 0.063
Detector resolution: 10.4002 pixels mm-1θmax = 25.1°, θmin = 3.1°
ω scansh = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −25→27
Tmin = 0.782, Tmax = 0.959l = −8→8
12548 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.1062P)2P] where P = (Fo2 + 2Fc2)/3
3072 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Geometry. 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.
xyzUiso*/Ueq
C11.1372 (3)0.84277 (15)0.6837 (5)0.0588 (9)
H11.21520.86040.74470.071*
C21.0316 (3)0.87560 (16)0.6029 (5)0.0630 (9)
C30.9120 (3)0.85005 (15)0.5039 (5)0.0606 (9)
H30.84140.87340.44780.073*
C40.9004 (3)0.79165 (14)0.4907 (5)0.0539 (8)
C51.0717 (4)0.60054 (16)0.6391 (5)0.0672 (9)
H50.99050.58570.58020.081*
C61.1712 (4)0.56449 (18)0.7170 (6)0.0774 (11)
H61.15780.52470.71030.093*
C71.2939 (4)0.5859 (2)0.8075 (6)0.0824 (12)
H71.36080.56030.85950.099*
C81.3169 (4)0.64432 (19)0.8204 (6)0.0740 (10)
H81.39900.65790.88120.089*
C91.2292 (3)0.74378 (17)0.7518 (5)0.0586 (9)
N100.9955 (2)0.69822 (11)0.5708 (4)0.0525 (7)
H100.92130.68400.51280.063*
C111.1281 (3)0.78210 (15)0.6748 (4)0.0532 (8)
C121.0075 (3)0.75623 (14)0.5787 (4)0.0507 (8)
C131.2163 (3)0.68400 (16)0.7418 (5)0.0606 (9)
C141.0924 (3)0.66091 (15)0.6481 (4)0.0552 (8)
O151.0275 (2)0.93401 (11)0.6023 (4)0.0789 (8)
C161.1437 (4)0.96502 (17)0.6957 (6)0.0822 (11)
H16A1.12611.00570.69330.123*
H16B1.20380.95770.62630.123*
H16C1.17870.95230.82980.123*
O170.7946 (2)0.76076 (10)0.3978 (4)0.0661 (7)
C180.6815 (3)0.79154 (16)0.2905 (6)0.0708 (10)
H18A0.61460.76440.23130.106*
H18B0.69850.81450.18940.106*
H18C0.65570.81640.37890.106*
Cl191.37790 (8)0.77318 (5)0.86037 (16)0.0835 (4)
S200.67506 (9)0.60826 (4)0.27655 (15)0.0686 (4)
O210.7046 (4)0.56795 (15)0.1495 (6)0.1301 (14)
O220.5948 (3)0.65462 (13)0.1825 (5)0.1074 (11)
O230.7793 (2)0.62580 (14)0.4408 (5)0.0967 (9)
C240.5785 (4)0.56702 (17)0.3904 (6)0.0738 (10)
F250.6355 (3)0.52276 (13)0.4837 (5)0.1314 (12)
F260.5357 (4)0.59810 (14)0.5057 (6)0.1486 (14)
F270.4759 (3)0.54695 (15)0.2592 (5)0.1493 (14)
U11U22U33U12U13U23
C10.054 (2)0.065 (2)0.0553 (19)−0.0088 (16)0.0140 (17)−0.0015 (16)
C20.063 (2)0.063 (2)0.065 (2)−0.0052 (18)0.0233 (19)0.0038 (17)
C30.052 (2)0.060 (2)0.069 (2)0.0021 (16)0.0174 (17)0.0038 (16)
C40.0440 (19)0.060 (2)0.0566 (19)0.0002 (15)0.0145 (16)0.0040 (15)
C50.063 (2)0.068 (2)0.066 (2)0.0039 (18)0.0139 (18)0.0018 (18)
C60.085 (3)0.068 (2)0.075 (2)0.021 (2)0.019 (2)0.004 (2)
C70.069 (3)0.091 (3)0.078 (3)0.027 (2)0.010 (2)0.001 (2)
C80.054 (2)0.092 (3)0.068 (2)0.016 (2)0.0068 (18)0.002 (2)
C90.0459 (19)0.079 (2)0.0499 (19)−0.0051 (17)0.0143 (16)−0.0011 (16)
N100.0432 (15)0.0611 (17)0.0512 (15)−0.0001 (12)0.0117 (12)0.0015 (12)
C110.0461 (19)0.070 (2)0.0451 (17)0.0013 (16)0.0166 (15)0.0014 (15)
C120.048 (2)0.061 (2)0.0460 (17)0.0001 (15)0.0194 (15)−0.0001 (14)
C130.047 (2)0.083 (3)0.0505 (19)0.0091 (17)0.0132 (16)0.0031 (17)
C140.052 (2)0.065 (2)0.0497 (18)0.0068 (16)0.0174 (16)0.0027 (16)
O150.0707 (17)0.0567 (15)0.1022 (19)−0.0073 (13)0.0168 (15)−0.0006 (13)
C160.082 (3)0.067 (2)0.087 (3)−0.022 (2)0.011 (2)−0.002 (2)
O170.0444 (14)0.0601 (14)0.0823 (17)−0.0032 (11)0.0030 (12)0.0067 (12)
C180.045 (2)0.071 (2)0.086 (3)0.0088 (17)0.0050 (19)0.0042 (19)
Cl190.0457 (6)0.1037 (8)0.0908 (7)−0.0074 (5)0.0067 (5)−0.0076 (6)
S200.0630 (6)0.0553 (6)0.0846 (7)−0.0041 (4)0.0190 (5)0.0067 (5)
O210.186 (4)0.090 (2)0.156 (3)−0.022 (2)0.114 (3)−0.022 (2)
O220.082 (2)0.0794 (19)0.138 (3)−0.0040 (16)0.0005 (19)0.0429 (18)
O230.0595 (16)0.099 (2)0.115 (2)−0.0209 (16)0.0038 (16)0.0111 (18)
C240.063 (2)0.066 (2)0.089 (3)−0.001 (2)0.021 (2)0.005 (2)
F250.112 (2)0.109 (2)0.178 (3)0.0179 (17)0.052 (2)0.080 (2)
F260.165 (3)0.122 (2)0.210 (4)−0.025 (2)0.132 (3)−0.023 (2)
F270.111 (2)0.174 (3)0.136 (3)−0.081 (2)−0.001 (2)0.033 (2)
C1—C21.360 (5)N10—C121.346 (4)
C1—C111.405 (5)N10—C141.351 (4)
C1—H10.9300N10—H100.8600
C2—O151.351 (4)C11—C121.426 (4)
C2—C31.418 (5)C13—C141.427 (5)
C3—C41.356 (5)O15—C161.439 (4)
C3—H30.9300C16—H16A0.9600
C4—O171.354 (4)C16—H16B0.9600
C4—C121.414 (4)C16—H16C0.9600
C5—C61.353 (5)O17—C181.434 (4)
C5—C141.412 (5)C18—H18A0.9600
C5—H50.9300C18—H18B0.9600
C6—C71.398 (6)C18—H18C0.9600
C6—H60.9300S20—O211.408 (3)
C7—C81.370 (6)S20—O221.419 (3)
C7—H70.9300S20—O231.422 (3)
C8—C131.415 (5)S20—C241.803 (4)
C8—H80.9300C24—F251.275 (4)
C9—C131.388 (5)C24—F261.289 (4)
C9—C111.396 (5)C24—F271.310 (5)
C9—Cl191.723 (3)
C2—C1—C11119.9 (3)N10—C12—C11120.2 (3)
C2—C1—H1120.1C4—C12—C11119.8 (3)
C11—C1—H1120.1C9—C13—C8124.7 (3)
O15—C2—C1125.6 (3)C9—C13—C14117.7 (3)
O15—C2—C3112.9 (3)C8—C13—C14117.6 (4)
C1—C2—C3121.4 (3)N10—C14—C5121.1 (3)
C4—C3—C2120.1 (3)N10—C14—C13118.3 (3)
C4—C3—H3119.9C5—C14—C13120.6 (3)
C2—C3—H3119.9C2—O15—C16118.2 (3)
O17—C4—C3127.4 (3)O15—C16—H16A109.5
O17—C4—C12112.8 (3)O15—C16—H16B109.5
C3—C4—C12119.9 (3)H16A—C16—H16B109.5
C6—C5—C14119.4 (4)O15—C16—H16C109.5
C6—C5—H5120.3H16A—C16—H16C109.5
C14—C5—H5120.3H16B—C16—H16C109.5
C5—C6—C7121.2 (4)C4—O17—C18118.4 (3)
C5—C6—H6119.4O17—C18—H18A109.5
C7—C6—H6119.4O17—C18—H18B109.5
C8—C7—C6120.9 (4)H18A—C18—H18B109.5
C8—C7—H7119.6O17—C18—H18C109.5
C6—C7—H7119.6H18A—C18—H18C109.5
C7—C8—C13120.4 (4)H18B—C18—H18C109.5
C7—C8—H8119.8O21—S20—O22115.5 (2)
C13—C8—H8119.8O21—S20—O23115.4 (2)
C13—C9—C11123.7 (3)O22—S20—O23113.59 (19)
C13—C9—Cl19118.9 (3)O21—S20—C24103.3 (2)
C11—C9—Cl19117.4 (3)O22—S20—C24104.03 (19)
C12—N10—C14124.3 (3)O23—S20—C24102.66 (19)
C12—N10—H10117.9F25—C24—F26109.4 (4)
C14—N10—H10117.9F25—C24—F27105.4 (4)
C9—C11—C1125.3 (3)F26—C24—F27104.2 (4)
C9—C11—C12115.8 (3)F25—C24—S20113.3 (3)
C1—C11—C12118.8 (3)F26—C24—S20112.4 (3)
N10—C12—C4120.0 (3)F27—C24—S20111.5 (3)
C11—C1—C2—O15179.7 (3)Cl19—C9—C13—C82.0 (5)
C11—C1—C2—C3−1.8 (5)C11—C9—C13—C14−0.3 (5)
O15—C2—C3—C4179.7 (3)Cl19—C9—C13—C14−179.0 (2)
C1—C2—C3—C41.1 (5)C7—C8—C13—C9178.3 (3)
C2—C3—C4—O17−178.2 (3)C7—C8—C13—C14−0.7 (5)
C2—C3—C4—C121.0 (5)C12—N10—C14—C5178.1 (3)
C14—C5—C6—C70.5 (6)C12—N10—C14—C13−1.1 (4)
C5—C6—C7—C80.2 (6)C6—C5—C14—N10179.6 (3)
C6—C7—C8—C13−0.1 (6)C6—C5—C14—C13−1.2 (5)
C13—C9—C11—C1179.4 (3)C9—C13—C14—N101.5 (4)
Cl19—C9—C11—C1−2.0 (4)C8—C13—C14—N10−179.5 (3)
C13—C9—C11—C12−1.2 (4)C9—C13—C14—C5−177.7 (3)
Cl19—C9—C11—C12177.4 (2)C8—C13—C14—C51.3 (5)
C2—C1—C11—C9180.0 (3)C1—C2—O15—C16−0.5 (5)
C2—C1—C11—C120.6 (5)C3—C2—O15—C16−179.0 (3)
C14—N10—C12—C4179.1 (3)C3—C4—O17—C183.6 (5)
C14—N10—C12—C11−0.6 (4)C12—C4—O17—C18−175.7 (3)
O17—C4—C12—N10−2.6 (4)O21—S20—C24—F2559.0 (4)
C3—C4—C12—N10178.1 (3)O22—S20—C24—F25−180.0 (3)
O17—C4—C12—C11177.1 (3)O23—S20—C24—F25−61.4 (4)
C3—C4—C12—C11−2.2 (4)O21—S20—C24—F26−176.3 (4)
C9—C11—C12—N101.7 (4)O22—S20—C24—F26−55.3 (4)
C1—C11—C12—N10−178.9 (3)O23—S20—C24—F2663.3 (4)
C9—C11—C12—C4−178.0 (3)O21—S20—C24—F27−59.7 (4)
C1—C11—C12—C41.4 (4)O22—S20—C24—F2761.3 (4)
C11—C9—C13—C8−179.3 (3)O23—S20—C24—F27179.9 (3)
D—H···AD—HH···AD···AD—H···A
N10—H10···O230.862.012.826 (4)159
C5—H5···O230.932.423.151 (5)136
C8—H8···O22i0.932.533.348 (6)147
C18—H18A···O220.962.563.326 (5)137
C18—H18C···O22ii0.962.553.462 (5)158
CgICgJCg···CgDihedral angleInterplanar distance
11iii3.817 (2)0.333.506 (2)
11ii3.817 (2)0.333.499 (2)
12iii3.984 (2)1.193.484 (2)
12ii3.616 (2)1.193.493 (2)
23iii3.919 (2)1.953.490 (2)
32ii3.919 (2)1.953.509 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N10—H10⋯O230.862.012.826 (4)159
C5—H5⋯O230.932.423.151 (5)136
C8—H8⋯O22i0.932.533.348 (6)147
C18—H18A⋯O220.962.563.326 (5)137
C18—H18C⋯O22ii0.962.553.462 (5)158

Symmetry codes: (i) ; (ii) .

Table 2

π–π Interactions (Å,°)

CgICgJCg⋯CgDihedral angleInterplanar distance
11iii3.817 (2)0.333.506 (2)
11ii3.817 (2)0.333.499 (2)
12iii3.984 (2)1.193.484 (2)
12ii3.616 (2)1.193.493 (2)
23iii3.919 (2)1.953.490 (2)
32ii3.919 (2)1.953.509 (2)

Symmetry codes: (ii) ; (iii) Cg1, Cg2 and Cg3 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12 and C5–C8/C13/C14 rings, respectively. Cg⋯Cg is the distance between ring centroids. The dihedral angle is that between the planes of the rings. The interplanar distance is the perpendicular distance of CgI from ring J.

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2.  9-Phenyl-10H-acridinium trifluoro-methane-sulfonate.

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