Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042663/xu2311sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042663/xu2311Isup2.hkl |
CCDC reference: 663699
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.095
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT410_ALERT_2_B Short Intra H...H Contact H5 .. H16A .. 1.89 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized by treating 9(10H)-acridinone with five molar excess of ethyl iodoacetate, both dissolved in dry dimethylsulfoxide, in the presence of anhydrous potassium carbonate (323 K, 8 h). The reaction mixture was poured into diluted hydrochloric acid, and the crude product was isolated by filtration and purified by gravitational column chromatography (SiO2, chloroform/ethanol, 10:1 v/v). Yellow crystals of (I) suitable for X-ray investigations were grown from acetone [m.p. = 455–457 K; elemental analysis (% calculated/found): C 72.58/72.36, H 5.37/5.26, N 4.98/4.96].
Methyl H atoms were placed in calculated positions with C—H = 0.98 Å and torsion angle was refined to fit the electron density, Uiso(H) = 1.5Ueq(C). Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 (aromatic) and 0.99 Å (methylene), and refined in riding mode with Uiso(H) = 1.2Ueq(C).
9-Acridinones strongly fluoresce in visible region (Boużyk et al., 2003) which brings about that they can serve as emitting fragments of fluorogenic indicators or labels. 9-Acridinone derivatives attached through a spacer to macromolcules have been applied among others in fluorometric assay of peptides (Faller et al., 1997) and avidin or streptavidin (Agiamarnioti et al., 2006). A highly sensitive assay for antibody catalysis has also been demonstrated by using a number of 9-acridinone labelled compounds (Reymond et al., 1996). Our investigations have been focused on search for 9-acridinone indicators exhibiting moderate polarity and ability to be transported through cell membranes and accumulated selectivity in various tissues. Ethyl 9-(2-oxoacridin-10(9H)-yl)acetate, (I), is the ethyl ester of (9-oxoacridin-10(9H)-yl) acetic acid whose crystal structure was determined in the past (Dobrzynska & Turowska-Tyrk, 1997).
The parameters characterizing the geometry (Figure 1) of the title compound (Table 1) are typical for 9-acridinones (Dobrzynska & Turowska-Tyrk, 1997; Dzyabchenko et al., 1980; Zavodnik et al., 1979; Zavodnik et al., 1981).
In the monoclinic crystal structure of (I), molecules related by a centre of symmetry are arranged in pairs stabilized via π-π interactions between acridinone units (Table 3, Figure 2). With average deviation from planarity of 0.030 Å, acridinone ring systems (given by C1—C9, N10, C11—C14 atoms) are parallel in pairs, whereas those in adjacent pairs are inclined to each other either at 0.0 (1)° (parallely oriented pairs) or 85.8 (1)° (perpendicularly oriented pairs). Parallely oriented pairs are linked by π-π interactions (Table 3, Figure 2), while perpendicularly oriented pairs - through the network of C—H···O interactions involving acridinone and carbonyl O atoms (Table 2, Figure 2). The view along the c axis demonstrates the arrangement of the acridinone ring in a herringbone pattern.
For general background, see: Agiamarnioti et al. (2006); Boużyk et al. (2003); Faller et al. (1997); Reymond et al. (1996). For related structures, see: Dobrzynska & Turowska-Tyrk (1997); Dzyabchenko et al. (1980); Zavodnik et al. (1979, 1981).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
C17H15NO3 | F(000) = 592 |
Mr = 281.30 | Dx = 1.350 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2420 reflections |
a = 11.3232 (3) Å | θ = 3.3–25.0° |
b = 10.3380 (2) Å | µ = 0.09 mm−1 |
c = 11.8925 (3) Å | T = 100 K |
β = 96.069 (2)° | Block, yellow |
V = 1384.33 (6) Å3 | 0.26 × 0.26 × 0.12 mm |
Z = 4 |
Oxford Diffraction GEMINI R ULTRA diffractometer | 2426 independent reflections |
Radiation source: fine-focus sealed tube | 1776 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 25.0°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | h = −12→13 |
Tmin = 0.978, Tmax = 0.991 | k = −12→12 |
8822 measured reflections | l = −14→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
2426 reflections | Δρmax = 0.19 e Å−3 |
191 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: none |
C17H15NO3 | V = 1384.33 (6) Å3 |
Mr = 281.30 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.3232 (3) Å | µ = 0.09 mm−1 |
b = 10.3380 (2) Å | T = 100 K |
c = 11.8925 (3) Å | 0.26 × 0.26 × 0.12 mm |
β = 96.069 (2)° |
Oxford Diffraction GEMINI R ULTRA diffractometer | 2426 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 1776 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.991 | Rint = 0.022 |
8822 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.19 e Å−3 |
2426 reflections | Δρmin = −0.20 e Å−3 |
191 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.74768 (11) | 0.07698 (13) | 0.59379 (11) | 0.0255 (3) | |
H1 | 0.7852 | 0.0956 | 0.6673 | 0.031* | |
C2 | 0.79552 (12) | −0.01492 (14) | 0.53008 (12) | 0.0301 (4) | |
H2 | 0.8643 | −0.0614 | 0.5594 | 0.036* | |
C3 | 0.74185 (12) | −0.03963 (14) | 0.42115 (12) | 0.0318 (4) | |
H3 | 0.7762 | −0.1013 | 0.3751 | 0.038* | |
C4 | 0.64007 (12) | 0.02402 (13) | 0.37971 (12) | 0.0272 (3) | |
H4 | 0.6049 | 0.0057 | 0.3053 | 0.033* | |
C5 | 0.33185 (11) | 0.34410 (12) | 0.42677 (11) | 0.0235 (3) | |
H5 | 0.2908 | 0.3207 | 0.3559 | 0.028* | |
C6 | 0.29030 (11) | 0.44419 (13) | 0.48748 (11) | 0.0263 (3) | |
H6 | 0.2210 | 0.4894 | 0.4576 | 0.032* | |
C7 | 0.34785 (12) | 0.48082 (13) | 0.59227 (12) | 0.0267 (3) | |
H7 | 0.3188 | 0.5508 | 0.6332 | 0.032* | |
C8 | 0.44674 (11) | 0.41402 (12) | 0.63490 (11) | 0.0238 (3) | |
H8 | 0.4859 | 0.4377 | 0.7066 | 0.029* | |
C9 | 0.59786 (11) | 0.24433 (12) | 0.62432 (11) | 0.0220 (3) | |
N10 | 0.48050 (9) | 0.17667 (10) | 0.40685 (8) | 0.0211 (3) | |
C11 | 0.64392 (11) | 0.14521 (12) | 0.55352 (11) | 0.0209 (3) | |
C12 | 0.58718 (11) | 0.11590 (12) | 0.44574 (11) | 0.0213 (3) | |
C13 | 0.49175 (11) | 0.31132 (12) | 0.57522 (10) | 0.0202 (3) | |
C14 | 0.43467 (10) | 0.27592 (12) | 0.46854 (10) | 0.0194 (3) | |
O15 | 0.64646 (8) | 0.27032 (9) | 0.72029 (7) | 0.0296 (3) | |
C16 | 0.42514 (12) | 0.14381 (13) | 0.29409 (10) | 0.0226 (3) | |
H16A | 0.3399 | 0.1672 | 0.2881 | 0.027* | |
H16B | 0.4308 | 0.0493 | 0.2824 | 0.027* | |
C17 | 0.48365 (11) | 0.21345 (12) | 0.20307 (11) | 0.0224 (3) | |
O18 | 0.44395 (8) | 0.16691 (8) | 0.10116 (7) | 0.0251 (3) | |
C19 | 0.49230 (12) | 0.22930 (14) | 0.00575 (11) | 0.0269 (3) | |
H19B | 0.5781 | 0.2099 | 0.0073 | 0.032* | |
H19A | 0.4824 | 0.3243 | 0.0100 | 0.032* | |
C20 | 0.42657 (16) | 0.17831 (15) | −0.10081 (12) | 0.0428 (4) | |
H20C | 0.4328 | 0.0838 | −0.1020 | 0.064* | |
H20B | 0.4610 | 0.2145 | −0.1662 | 0.064* | |
H20A | 0.3428 | 0.2033 | −0.1040 | 0.064* | |
O21 | 0.55459 (8) | 0.29938 (9) | 0.21883 (8) | 0.0341 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0215 (7) | 0.0294 (8) | 0.0253 (7) | −0.0023 (6) | 0.0007 (6) | 0.0009 (6) |
C2 | 0.0221 (8) | 0.0314 (8) | 0.0365 (9) | 0.0054 (6) | 0.0022 (7) | 0.0000 (7) |
C3 | 0.0308 (8) | 0.0309 (8) | 0.0348 (9) | 0.0037 (6) | 0.0087 (7) | −0.0051 (7) |
C4 | 0.0287 (8) | 0.0291 (8) | 0.0238 (8) | −0.0002 (6) | 0.0029 (6) | −0.0043 (6) |
C5 | 0.0232 (7) | 0.0267 (7) | 0.0194 (7) | −0.0019 (6) | −0.0028 (6) | 0.0018 (6) |
C6 | 0.0210 (7) | 0.0275 (8) | 0.0295 (8) | 0.0018 (6) | −0.0015 (6) | 0.0029 (6) |
C7 | 0.0260 (8) | 0.0248 (7) | 0.0291 (8) | 0.0027 (6) | 0.0018 (6) | −0.0043 (6) |
C8 | 0.0244 (7) | 0.0267 (7) | 0.0200 (7) | −0.0025 (6) | 0.0007 (6) | −0.0026 (6) |
C9 | 0.0207 (7) | 0.0264 (7) | 0.0186 (7) | −0.0029 (6) | 0.0007 (6) | 0.0013 (6) |
N10 | 0.0207 (6) | 0.0259 (6) | 0.0160 (6) | 0.0000 (5) | −0.0006 (5) | −0.0019 (5) |
C11 | 0.0183 (7) | 0.0225 (7) | 0.0219 (7) | −0.0022 (5) | 0.0021 (6) | 0.0015 (6) |
C12 | 0.0206 (7) | 0.0219 (7) | 0.0216 (7) | −0.0021 (5) | 0.0034 (6) | 0.0018 (6) |
C13 | 0.0182 (7) | 0.0226 (7) | 0.0199 (7) | −0.0031 (5) | 0.0018 (5) | 0.0005 (6) |
C14 | 0.0195 (7) | 0.0204 (7) | 0.0183 (7) | −0.0041 (6) | 0.0020 (6) | 0.0003 (5) |
O15 | 0.0279 (5) | 0.0393 (6) | 0.0198 (5) | 0.0057 (4) | −0.0055 (4) | −0.0047 (4) |
C16 | 0.0236 (7) | 0.0259 (7) | 0.0179 (7) | −0.0035 (6) | 0.0005 (6) | −0.0040 (6) |
C17 | 0.0207 (7) | 0.0242 (7) | 0.0216 (7) | −0.0008 (6) | −0.0005 (6) | −0.0033 (6) |
O18 | 0.0305 (5) | 0.0283 (5) | 0.0166 (5) | −0.0085 (4) | 0.0027 (4) | −0.0011 (4) |
C19 | 0.0308 (8) | 0.0290 (7) | 0.0221 (8) | −0.0046 (6) | 0.0082 (6) | 0.0010 (6) |
C20 | 0.0590 (11) | 0.0476 (9) | 0.0222 (8) | −0.0208 (8) | 0.0055 (8) | 0.0000 (7) |
O21 | 0.0375 (6) | 0.0378 (6) | 0.0270 (6) | −0.0165 (5) | 0.0032 (5) | −0.0067 (5) |
C1—C2 | 1.363 (2) | C9—C11 | 1.4574 (18) |
C1—C11 | 1.4100 (17) | C9—O15 | 1.2428 (14) |
C1—H1 | 0.9500 | N10—C12 | 1.3962 (16) |
C2—C3 | 1.3951 (19) | N10—C14 | 1.3932 (16) |
C2—H2 | 0.9500 | N10—C16 | 1.4591 (15) |
C3—C4 | 1.3725 (19) | C11—C12 | 1.4048 (17) |
C3—H3 | 0.9500 | C13—C14 | 1.4099 (16) |
C4—C12 | 1.4061 (19) | C16—C17 | 1.5102 (19) |
C4—H4 | 0.9500 | C16—H16A | 0.9900 |
C5—C6 | 1.3731 (19) | C16—H16B | 0.9900 |
C5—C14 | 1.4060 (17) | C17—O18 | 1.3369 (15) |
C5—H5 | 0.9500 | C17—O21 | 1.1990 (15) |
C6—C7 | 1.3962 (18) | O18—C19 | 1.4610 (16) |
C6—H6 | 0.9500 | C19—C20 | 1.4961 (18) |
C7—C8 | 1.3666 (18) | C19—H19B | 0.9900 |
C7—H7 | 0.9500 | C19—H19A | 0.9900 |
C8—C13 | 1.4026 (18) | C20—H20C | 0.9800 |
C8—H8 | 0.9500 | C20—H20B | 0.9800 |
C9—C13 | 1.4546 (17) | C20—H20A | 0.9800 |
C2—C1—C11 | 121.73 (12) | C1—C11—C9 | 119.45 (11) |
C2—C1—H1 | 119.1 | N10—C12—C11 | 120.09 (12) |
C11—C1—H1 | 119.1 | N10—C12—C4 | 121.58 (11) |
C1—C2—C3 | 118.96 (12) | C11—C12—C4 | 118.33 (11) |
C1—C2—H2 | 120.5 | C8—C13—C14 | 119.69 (11) |
C3—C2—H2 | 120.5 | C8—C13—C9 | 119.09 (11) |
C4—C3—C2 | 120.83 (14) | C14—C13—C9 | 121.22 (12) |
C4—C3—H3 | 119.6 | N10—C14—C5 | 121.58 (11) |
C2—C3—H3 | 119.6 | N10—C14—C13 | 120.28 (11) |
C3—C4—C12 | 120.96 (12) | C5—C14—C13 | 118.14 (12) |
C3—C4—H4 | 119.5 | N10—C16—H16A | 109.3 |
C12—C4—H4 | 119.5 | C17—C16—H16A | 109.3 |
C6—C5—C14 | 120.59 (12) | N10—C16—H16B | 109.3 |
C6—C5—H5 | 119.7 | C17—C16—H16B | 109.3 |
C14—C5—H5 | 119.7 | H16B—C16—H16B | 107.9 |
C5—C6—C7 | 121.35 (12) | C16—C17—O18 | 110.32 (10) |
C5—C6—H6 | 119.3 | C16—C17—O21 | 125.35 (12) |
C7—C6—H6 | 119.3 | C17—O18—C19 | 115.31 (9) |
C8—C7—C6 | 118.74 (13) | O18—C17—O21 | 124.32 (12) |
C8—C7—H7 | 120.6 | O18—C19—C20 | 107.97 (11) |
C6—C7—H7 | 120.6 | O18—C19—H19B | 110.1 |
C7—C8—C13 | 121.47 (11) | C20—C19—H19B | 110.1 |
C7—C8—H8 | 119.3 | O18—C19—H19A | 110.1 |
C13—C8—H8 | 119.3 | C20—C19—H19A | 110.1 |
O15—C9—C13 | 122.17 (12) | H19B—C19—H19A | 108.4 |
O15—C9—C11 | 122.13 (11) | C19—C20—H20C | 109.5 |
N10—C16—C17 | 111.68 (10) | C19—C20—H20B | 109.5 |
C11—C9—C13 | 115.70 (11) | H20C—C20—H20B | 109.5 |
C12—N10—C14 | 120.95 (10) | C19—C20—H20A | 109.5 |
C14—N10—C16 | 120.51 (10) | H20C—C20—H20A | 109.5 |
C12—C11—C1 | 119.10 (12) | H20B—C20—H20A | 109.5 |
C12—C11—C9 | 121.45 (11) | ||
C11—C1—C2—C3 | 1.6 (2) | C9—C11—C12—C4 | 176.68 (12) |
C1—C2—C3—C4 | −2.3 (2) | C3—C4—C12—N10 | −176.76 (12) |
C2—C3—C4—C12 | 0.1 (2) | C3—C4—C12—C11 | 2.7 (2) |
C14—C5—C6—C7 | −0.4 (2) | C7—C8—C13—C14 | 0.3 (2) |
C5—C6—C7—C8 | −0.7 (2) | C7—C8—C13—C9 | 179.52 (12) |
C6—C7—C8—C13 | 0.7 (2) | O15—C9—C13—C8 | 4.02 (19) |
C2—C1—C11—C12 | 1.2 (2) | C11—C9—C13—C8 | −175.67 (11) |
C2—C1—C11—C9 | −178.80 (12) | O15—C9—C13—C14 | −176.81 (12) |
O15—C9—C11—C12 | 179.25 (12) | C12—N10—C14—C5 | 175.47 (12) |
C13—C9—C11—C12 | −1.06 (18) | C16—N10—C14—C5 | 2.45 (18) |
O15—C9—C11—C1 | −0.74 (19) | C16—N10—C14—C13 | −177.02 (11) |
C13—C9—C11—C1 | 178.95 (11) | C6—C5—C14—N10 | −178.01 (12) |
C14—N10—C12—C11 | 6.44 (18) | C6—C5—C14—C13 | 1.47 (19) |
C16—N10—C12—C11 | 179.62 (11) | C8—C13—C14—N10 | 178.06 (11) |
C14—N10—C12—C4 | −174.07 (11) | C9—C13—C14—N10 | −1.10 (18) |
C16—N10—C12—C4 | −0.88 (18) | C8—C13—C14—C5 | −1.43 (18) |
C1—C11—C12—C4 | −3.34 (19) | C9—C13—C14—C5 | 179.41 (11) |
N10—C16—C17—O18 | 170.44 (10) | C14—N10—C16—C17 | 93.93 (13) |
N10—C16—C17—O21 | −10.40 (19) | C12—N10—C16—C17 | −79.29 (14) |
C11—C9—C13—C14 | 3.50 (18) | O21—C17—O18—C19 | −0.61 (18) |
C12—N10—C14—C13 | −4.00 (18) | C16—C17—O18—C19 | 178.56 (10) |
C1—C11—C12—N10 | 176.17 (11) | C17—O18—C19—C20 | −172.36 (12) |
C9—C11—C12—N10 | −3.82 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O21i | 0.95 | 2.53 | 3.4155 (17) | 154 |
C5—H5···O15ii | 0.95 | 2.37 | 3.2781 (15) | 161 |
C16—H16A···O15ii | 0.99 | 2.34 | 3.3061 (16) | 164 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H15NO3 |
Mr | 281.30 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 11.3232 (3), 10.3380 (2), 11.8925 (3) |
β (°) | 96.069 (2) |
V (Å3) | 1384.33 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.26 × 0.26 × 0.12 |
Data collection | |
Diffractometer | Oxford Diffraction GEMINI R ULTRA |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.978, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8822, 2426, 1776 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.095, 0.98 |
No. of reflections | 2426 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.20 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
C9—C11 | 1.4574 (18) | C17—O18 | 1.3369 (15) |
C9—O15 | 1.2428 (14) | C17—O21 | 1.1990 (15) |
N10—C16 | 1.4591 (15) | O18—C19 | 1.4610 (16) |
N10—C16—C17 | 111.68 (10) | C16—C17—O21 | 125.35 (12) |
C11—C9—C13 | 115.70 (11) | C17—O18—C19 | 115.31 (9) |
C12—N10—C14 | 120.95 (10) | O18—C17—O21 | 124.32 (12) |
C14—N10—C16 | 120.51 (10) | O18—C19—C20 | 107.97 (11) |
C16—C17—O18 | 110.32 (10) | ||
C1—C11—C12—C4 | −3.34 (19) | C11—C9—C13—C14 | 3.50 (18) |
N10—C16—C17—O18 | 170.44 (10) | C12—N10—C14—C13 | −4.00 (18) |
N10—C16—C17—O21 | −10.40 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O21i | 0.95 | 2.53 | 3.4155 (17) | 154 |
C5—H5···O15ii | 0.95 | 2.37 | 3.2781 (15) | 161 |
C16—H16A···O15ii | 0.99 | 2.34 | 3.3061 (16) | 164 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
CgI | CgJ | Cg···Cg | Dihedral angle | Interplanar distance | Offset |
1 | 2iii | 3.780 (1) | 3.1 | 3.492 | 1.361 (3) |
2 | 1iii | 3.780 (1) | 3.1 | 3.417 | 1.422 (3) |
3 | 3iv | 3.660 (1) | 0.0 | 3.530 | 1.853 (3) |
Symmetry codes: (iii) 1-x, -y, 1-z ; (iv) 1-x, 1-y, 1-z. Notes: Cg1 is the centroid of ring C9/C11/C12/N10/C14/C13, Cg2 is the centroid of ring C1–C4/C12/C11 and Cg3 is the centroid of ring C5–C8/C13/C14. Cg···Cg is the distance between ring centroids. The dihedral angle is that between the planes of rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. The offset is computed as the third side of the right-angled triangle involving the Cg···Cg distance. |
9-Acridinones strongly fluoresce in visible region (Boużyk et al., 2003) which brings about that they can serve as emitting fragments of fluorogenic indicators or labels. 9-Acridinone derivatives attached through a spacer to macromolcules have been applied among others in fluorometric assay of peptides (Faller et al., 1997) and avidin or streptavidin (Agiamarnioti et al., 2006). A highly sensitive assay for antibody catalysis has also been demonstrated by using a number of 9-acridinone labelled compounds (Reymond et al., 1996). Our investigations have been focused on search for 9-acridinone indicators exhibiting moderate polarity and ability to be transported through cell membranes and accumulated selectivity in various tissues. Ethyl 9-(2-oxoacridin-10(9H)-yl)acetate, (I), is the ethyl ester of (9-oxoacridin-10(9H)-yl) acetic acid whose crystal structure was determined in the past (Dobrzynska & Turowska-Tyrk, 1997).
The parameters characterizing the geometry (Figure 1) of the title compound (Table 1) are typical for 9-acridinones (Dobrzynska & Turowska-Tyrk, 1997; Dzyabchenko et al., 1980; Zavodnik et al., 1979; Zavodnik et al., 1981).
In the monoclinic crystal structure of (I), molecules related by a centre of symmetry are arranged in pairs stabilized via π-π interactions between acridinone units (Table 3, Figure 2). With average deviation from planarity of 0.030 Å, acridinone ring systems (given by C1—C9, N10, C11—C14 atoms) are parallel in pairs, whereas those in adjacent pairs are inclined to each other either at 0.0 (1)° (parallely oriented pairs) or 85.8 (1)° (perpendicularly oriented pairs). Parallely oriented pairs are linked by π-π interactions (Table 3, Figure 2), while perpendicularly oriented pairs - through the network of C—H···O interactions involving acridinone and carbonyl O atoms (Table 2, Figure 2). The view along the c axis demonstrates the arrangement of the acridinone ring in a herringbone pattern.