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The title compound, C
22H
17NO
3, crystallizes in the monoclinic space group
P2
1/
c with four molecules per unit cell. The molecules are arranged in centrosymmetric pairs, joined
via the C and attached H atoms in the
meta position relative to the methoxy group. These pairs are bonded in the crystalline phase as a result of non-specific dispersive interactions, and through a network of C—H
O interactions involving the non-bonded O atom of the carboxy group and, to some extent, the O atom of the methoxy group. The methoxy substituent lies in the plane of the almost planar acridine moiety and is directed towards the phenyl ester group. The phenyl ester group itself is twisted by 35.9 (5)° relative to the mean plane of the acridine moiety.
Supporting information
CCDC reference: 183003
2-Methoxyacridine-9-carboxylic acid and, subsequently, (I) were synthesized
following procedures outlined by Zomer et al. (1991) and Batmanghelich
et al. (1991). Light yellow needle crystals of (I) suitable for X-ray
investigations were grown from cyclohexane. NB Plate morphology given below -
which is correct?
All H atoms were placed in idealized positions and treated as riding, with C—H
= 0.96 Å and Uiso(H) = 1.2Ueq(C). Are these the correct
restraints?
Data collection: KM-4 Software (Kuma Diffraction, 1989); cell refinement: KM-4 Software; data reduction: KM-4 Software; 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.
2-Methylphenyl 2-methoxyacridine-9-carboxylate
top
Crystal data top
C22H17NO3 | F(000) = 720 |
Mr = 343.38 | Dx = 1.303 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.393 (3) Å | Cell parameters from 50 reflections |
b = 9.233 (2) Å | θ = 3–60.1° |
c = 14.162 (3) Å | µ = 0.09 mm−1 |
β = 91.81 (3)° | T = 293 K |
V = 1750.4 (7) Å3 | Plate, yellow |
Z = 4 | 0.6 × 0.5 × 0.3 mm |
Data collection top
Kuma KM-4 diffractometer | Rint = 0.027 |
Radiation source: fine-focus sealed tube | θmax = 30.1°, θmin = 1.5° |
Graphite monochromator | h = −18→18 |
θ/2θ scans | k = −13→0 |
7169 measured reflections | l = 0→19 |
5108 independent reflections | 3 standard reflections every 200 reflections |
2994 reflections with I > 2σ(I) | intensity decay: 1.2% |
Refinement top
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)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.0646P)2 + 0.3081P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5108 reflections | Δρmax = 0.19 e Å−3 |
236 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.020 (2) |
Crystal data top
C22H17NO3 | V = 1750.4 (7) Å3 |
Mr = 343.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.393 (3) Å | µ = 0.09 mm−1 |
b = 9.233 (2) Å | T = 293 K |
c = 14.162 (3) Å | 0.6 × 0.5 × 0.3 mm |
β = 91.81 (3)° | |
Data collection top
Kuma KM-4 diffractometer | Rint = 0.027 |
7169 measured reflections | 3 standard reflections every 200 reflections |
5108 independent reflections | intensity decay: 1.2% |
2994 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.19 e Å−3 |
5108 reflections | Δρmin = −0.17 e Å−3 |
236 parameters | |
Special details top
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
2σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.59097 (11) | 0.41613 (18) | −0.09582 (12) | 0.0502 (4) | |
H1A | 0.6184 | 0.4948 | −0.1310 | 0.060* | |
C2 | 0.49579 (12) | 0.3711 (2) | −0.11668 (12) | 0.0550 (4) | |
C3 | 0.45186 (13) | 0.2582 (2) | −0.06388 (14) | 0.0603 (5) | |
H3A | 0.3844 | 0.2299 | −0.0797 | 0.072* | |
C4 | 0.50355 (13) | 0.1937 (2) | 0.00725 (14) | 0.0592 (5) | |
H4A | 0.4705 | 0.1206 | 0.0430 | 0.071* | |
C5 | 0.80072 (15) | 0.1231 (2) | 0.19619 (13) | 0.0632 (5) | |
H5A | 0.7665 | 0.0512 | 0.2319 | 0.076* | |
C6 | 0.89839 (16) | 0.1507 (2) | 0.21846 (13) | 0.0643 (5) | |
H6A | 0.9323 | 0.0953 | 0.2671 | 0.077* | |
C7 | 0.94992 (14) | 0.2600 (2) | 0.17051 (12) | 0.0584 (4) | |
H7A | 1.0191 | 0.2798 | 0.1851 | 0.070* | |
C8 | 0.90309 (12) | 0.33905 (18) | 0.10165 (11) | 0.0497 (4) | |
H8A | 0.9373 | 0.4161 | 0.0706 | 0.060* | |
C9 | 0.74731 (11) | 0.38807 (16) | 0.00355 (10) | 0.0429 (3) | |
N10 | 0.65269 (11) | 0.16397 (16) | 0.10190 (10) | 0.0564 (4) | |
C11 | 0.64823 (11) | 0.35012 (16) | −0.02127 (11) | 0.0448 (4) | |
C12 | 0.60456 (12) | 0.23484 (18) | 0.03133 (12) | 0.0505 (4) | |
C13 | 0.80096 (11) | 0.31190 (16) | 0.07462 (10) | 0.0442 (3) | |
C14 | 0.74893 (13) | 0.19990 (18) | 0.12308 (11) | 0.0511 (4) | |
O15 | 0.43478 (9) | 0.42634 (17) | −0.18648 (10) | 0.0712 (4) | |
C16 | 0.47415 (15) | 0.5392 (3) | −0.24303 (15) | 0.0754 (6) | |
H16A | 0.4258 | 0.5710 | −0.2901 | 0.091* | |
H16B | 0.4917 | 0.6187 | −0.2020 | 0.091* | |
H16C | 0.5328 | 0.5050 | −0.2733 | 0.091* | |
C17 | 0.79747 (11) | 0.51169 (16) | −0.04380 (10) | 0.0419 (3) | |
O18 | 0.87542 (9) | 0.50795 (12) | −0.08261 (8) | 0.0563 (3) | |
O19 | 0.74354 (8) | 0.63370 (12) | −0.03415 (9) | 0.0559 (3) | |
C20 | 0.78277 (11) | 0.76557 (17) | −0.06727 (12) | 0.0480 (4) | |
C21 | 0.84416 (12) | 0.84502 (18) | −0.00600 (11) | 0.0514 (4) | |
C22 | 0.87118 (14) | 0.98224 (19) | −0.03643 (14) | 0.0606 (5) | |
H22A | 0.9163 | 1.0382 | 0.0030 | 0.073* | |
C23 | 0.84092 (15) | 1.0339 (2) | −0.12351 (16) | 0.0691 (5) | |
H23A | 0.8578 | 1.1317 | −0.1396 | 0.083* | |
C24 | 0.78175 (15) | 0.9510 (2) | −0.18316 (15) | 0.0729 (6) | |
H24A | 0.7652 | 0.9833 | −0.2462 | 0.087* | |
C25 | 0.75142 (13) | 0.8152 (2) | −0.15482 (13) | 0.0627 (5) | |
H25A | 0.7042 | 0.7594 | −0.1920 | 0.075* | |
C26 | 0.88080 (19) | 0.7860 (2) | 0.08752 (14) | 0.0773 (6) | |
H26A | 0.9206 | 0.8571 | 0.1208 | 0.093* | |
H26B | 0.8254 | 0.7589 | 0.1251 | 0.093* | |
H26C | 0.9209 | 0.7022 | 0.0756 | 0.093* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0444 (8) | 0.0523 (9) | 0.0541 (9) | −0.0101 (7) | 0.0031 (7) | −0.0046 (7) |
C2 | 0.0428 (8) | 0.0642 (11) | 0.0579 (10) | −0.0042 (8) | 0.0013 (7) | −0.0135 (8) |
C3 | 0.0404 (8) | 0.0680 (12) | 0.0729 (12) | −0.0144 (8) | 0.0070 (8) | −0.0175 (9) |
C4 | 0.0483 (9) | 0.0552 (10) | 0.0750 (12) | −0.0149 (8) | 0.0153 (8) | −0.0078 (9) |
C5 | 0.0734 (12) | 0.0592 (11) | 0.0574 (10) | −0.0035 (9) | 0.0110 (9) | 0.0107 (8) |
C6 | 0.0729 (12) | 0.0686 (12) | 0.0513 (10) | 0.0054 (10) | 0.0005 (9) | 0.0082 (9) |
C7 | 0.0576 (10) | 0.0660 (11) | 0.0513 (9) | 0.0020 (8) | −0.0014 (8) | −0.0017 (8) |
C8 | 0.0506 (9) | 0.0489 (9) | 0.0495 (9) | −0.0052 (7) | 0.0010 (7) | −0.0025 (7) |
C9 | 0.0441 (8) | 0.0399 (7) | 0.0451 (8) | −0.0062 (6) | 0.0061 (6) | −0.0062 (6) |
N10 | 0.0550 (8) | 0.0499 (8) | 0.0649 (9) | −0.0092 (7) | 0.0134 (7) | 0.0015 (7) |
C11 | 0.0415 (8) | 0.0425 (8) | 0.0509 (8) | −0.0066 (6) | 0.0078 (6) | −0.0087 (7) |
C12 | 0.0475 (9) | 0.0466 (9) | 0.0583 (10) | −0.0086 (7) | 0.0132 (7) | −0.0078 (7) |
C13 | 0.0473 (8) | 0.0411 (8) | 0.0444 (8) | −0.0030 (6) | 0.0074 (6) | −0.0054 (6) |
C14 | 0.0559 (10) | 0.0462 (9) | 0.0515 (9) | −0.0029 (7) | 0.0102 (7) | −0.0020 (7) |
O15 | 0.0466 (7) | 0.0947 (10) | 0.0716 (8) | −0.0104 (7) | −0.0092 (6) | 0.0008 (7) |
C16 | 0.0600 (12) | 0.0970 (16) | 0.0688 (12) | 0.0013 (11) | −0.0066 (10) | 0.0057 (12) |
C17 | 0.0404 (7) | 0.0456 (8) | 0.0396 (7) | −0.0073 (6) | −0.0008 (6) | −0.0046 (6) |
O18 | 0.0522 (6) | 0.0568 (7) | 0.0610 (7) | −0.0038 (5) | 0.0186 (5) | −0.0004 (5) |
O19 | 0.0470 (6) | 0.0419 (6) | 0.0798 (8) | −0.0040 (5) | 0.0169 (6) | 0.0032 (5) |
C20 | 0.0417 (8) | 0.0415 (8) | 0.0611 (10) | −0.0016 (6) | 0.0067 (7) | 0.0046 (7) |
C21 | 0.0532 (9) | 0.0458 (9) | 0.0554 (9) | −0.0009 (7) | 0.0043 (7) | 0.0006 (7) |
C22 | 0.0606 (11) | 0.0450 (9) | 0.0763 (12) | −0.0060 (8) | 0.0029 (9) | −0.0011 (8) |
C23 | 0.0678 (12) | 0.0503 (10) | 0.0899 (14) | −0.0041 (9) | 0.0124 (11) | 0.0191 (10) |
C24 | 0.0674 (12) | 0.0805 (14) | 0.0705 (12) | 0.0052 (11) | −0.0003 (10) | 0.0294 (11) |
C25 | 0.0518 (10) | 0.0699 (12) | 0.0658 (11) | −0.0031 (9) | −0.0068 (8) | 0.0061 (9) |
C26 | 0.1029 (17) | 0.0656 (13) | 0.0626 (12) | −0.0085 (12) | −0.0112 (11) | 0.0029 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.364 (2) | C11—C12 | 1.434 (2) |
C1—C11 | 1.422 (2) | C13—C14 | 1.434 (2) |
C1—H1A | 0.9600 | O15—C16 | 1.426 (2) |
C2—O15 | 1.361 (2) | C16—H16A | 0.9600 |
C2—C3 | 1.421 (3) | C16—H16B | 0.9600 |
C3—C4 | 1.343 (3) | C16—H16C | 0.9600 |
C3—H3A | 0.9601 | C17—O18 | 1.1955 (17) |
C4—C12 | 1.436 (2) | C17—O19 | 1.3474 (19) |
C4—H4A | 0.9600 | O19—C20 | 1.4121 (18) |
C5—C6 | 1.360 (3) | C20—C25 | 1.375 (2) |
C5—C14 | 1.418 (3) | C20—C21 | 1.386 (2) |
C5—H5A | 0.9600 | C21—C22 | 1.390 (2) |
C6—C7 | 1.410 (3) | C21—C26 | 1.500 (3) |
C6—H6A | 0.9600 | C22—C23 | 1.372 (3) |
C7—C8 | 1.356 (2) | C22—H22A | 0.9600 |
C7—H7A | 0.9600 | C23—C24 | 1.373 (3) |
C8—C13 | 1.431 (2) | C23—H23A | 0.9600 |
C8—H8A | 0.9600 | C24—C25 | 1.381 (3) |
C9—C11 | 1.406 (2) | C24—H24A | 0.9600 |
C9—C13 | 1.407 (2) | C25—H25A | 0.9600 |
C9—C17 | 1.494 (2) | C26—H26A | 0.9601 |
N10—C12 | 1.342 (2) | C26—H26B | 0.9599 |
N10—C14 | 1.355 (2) | C26—H26C | 0.9600 |
| | | |
C2—C1—C11 | 120.55 (16) | N10—C14—C13 | 122.93 (15) |
C2—C1—H1A | 119.2 | C5—C14—C13 | 118.43 (16) |
C11—C1—H1A | 120.2 | C9—C17—O18 | 126.57 (14) |
C1—C2—O15 | 125.33 (17) | C9—C17—O19 | 110.07 (12) |
C2—O15—C16 | 117.23 (14) | C11—C9—C17 | 120.82 (14) |
O15—C2—C3 | 114.07 (15) | O15—C16—H16A | 111.1 |
C1—C2—C3 | 120.60 (17) | O15—C16—H16B | 107.9 |
C4—C3—C2 | 120.50 (16) | O15—C16—H16C | 109.4 |
C4—C3—H3A | 120.8 | C17—O19—C20 | 118.74 (11) |
C2—C3—H3A | 118.6 | O18—C17—O19 | 123.33 (14) |
C3—C4—C12 | 121.35 (17) | C25—C20—C21 | 123.10 (15) |
C3—C4—H4A | 118.2 | C25—C20—O19 | 118.73 (15) |
C12—C4—H4A | 120.4 | C20—C21—C22 | 116.32 (16) |
C6—C5—C14 | 121.38 (17) | O19—C20—C21 | 117.90 (14) |
C6—C5—H5A | 118.6 | C20—C21—C26 | 122.10 (16) |
C14—C5—H5A | 120.0 | C22—C21—C26 | 121.58 (17) |
C5—C6—C7 | 120.28 (18) | C23—C22—C21 | 121.56 (18) |
C5—C6—H6A | 119.8 | C23—C22—H22A | 119.9 |
C7—C6—H6A | 119.9 | C21—C22—H22A | 118.4 |
C8—C7—C6 | 120.64 (18) | C22—C23—C24 | 120.52 (18) |
C8—C7—H7A | 118.3 | C22—C23—H23A | 118.4 |
C6—C7—H7A | 121.1 | C24—C23—H23A | 120.9 |
C7—C8—C13 | 120.98 (16) | C23—C24—C25 | 119.77 (18) |
C7—C8—H8A | 120.8 | C23—C24—H24A | 120.7 |
C13—C8—H8A | 118.3 | C25—C24—H24A | 119.4 |
C11—C9—C13 | 120.72 (14) | C20—C25—C24 | 118.70 (18) |
C13—C9—C17 | 118.45 (13) | C20—C25—H25A | 119.5 |
C12—N10—C14 | 118.46 (14) | C24—C25—H25A | 121.5 |
C9—C11—C1 | 124.13 (14) | C21—C26—H26A | 110.2 |
C9—C11—C12 | 116.88 (15) | C21—C26—H26B | 110.3 |
C1—C11—C12 | 118.97 (14) | C21—C26—H26C | 107.8 |
N10—C12—C11 | 123.66 (15) | H26A—C26—H26B | 109.5 |
N10—C12—C4 | 118.34 (15) | H26A—C26—H26C | 109.5 |
C11—C12—C4 | 118.00 (16) | H26B—C26—H26C | 109.5 |
C9—C13—C8 | 124.49 (14) | H16A—C16—H16C | 109.5 |
C9—C13—C14 | 117.27 (14) | H16A—C16—H16B | 109.5 |
C8—C13—C14 | 118.24 (14) | H16B—C16—H16C | 109.5 |
N10—C14—C5 | 118.64 (15) | | |
| | | |
C11—C1—C2—O15 | −179.79 (15) | C12—N10—C14—C13 | 1.2 (2) |
C11—C1—C2—C3 | 0.4 (3) | C6—C5—C14—N10 | 177.65 (17) |
O15—C2—C3—C4 | −179.97 (16) | C6—C5—C14—C13 | −2.2 (3) |
C1—C2—C3—C4 | −0.2 (3) | C9—C13—C14—N10 | 1.3 (2) |
C2—C3—C4—C12 | −0.9 (3) | C8—C13—C14—N10 | −178.89 (15) |
C14—C5—C6—C7 | 1.8 (3) | C9—C13—C14—C5 | −178.90 (14) |
C5—C6—C7—C8 | −0.1 (3) | C8—C13—C14—C5 | 0.9 (2) |
C6—C7—C8—C13 | −1.2 (3) | C1—C2—O15—C16 | 0.8 (3) |
C13—C9—C11—C1 | −176.25 (14) | C9—C17—O19—C20 | 174.73 (13) |
C17—C9—C11—C1 | 4.8 (2) | C3—C2—O15—C16 | −179.43 (16) |
C13—C9—C11—C12 | 2.1 (2) | C11—C9—C17—O18 | −125.80 (17) |
C17—C9—C11—C12 | −176.86 (13) | C13—C9—C17—O18 | 55.2 (2) |
C2—C1—C11—C9 | 178.71 (15) | C11—C9—C17—O19 | 56.37 (18) |
C2—C1—C11—C12 | 0.4 (2) | C13—C9—C17—O19 | −122.64 (14) |
C14—N10—C12—C11 | −2.1 (2) | O18—C17—O19—C20 | −3.2 (2) |
C14—N10—C12—C4 | 178.23 (15) | C17—O19—C20—C25 | 97.88 (18) |
C9—C11—C12—N10 | 0.5 (2) | C17—O19—C20—C21 | −87.90 (18) |
C1—C11—C12—N10 | 178.92 (15) | C25—C20—C21—C22 | 1.8 (2) |
C9—C11—C12—C4 | −179.85 (14) | O19—C20—C21—C22 | −172.16 (14) |
C1—C11—C12—C4 | −1.4 (2) | C25—C20—C21—C26 | −177.42 (18) |
C3—C4—C12—N10 | −178.61 (16) | O19—C20—C21—C26 | 8.6 (2) |
C3—C4—C12—C11 | 1.7 (3) | C20—C21—C22—C23 | −1.8 (3) |
C11—C9—C13—C8 | 177.28 (14) | C26—C21—C22—C23 | 177.36 (18) |
C17—C9—C13—C8 | −3.7 (2) | C21—C22—C23—C24 | 0.6 (3) |
C11—C9—C13—C14 | −2.9 (2) | C22—C23—C24—C25 | 0.8 (3) |
C17—C9—C13—C14 | 176.07 (13) | C21—C20—C25—C24 | −0.5 (3) |
C7—C8—C13—C9 | −179.49 (15) | O19—C20—C25—C24 | 173.45 (15) |
C7—C8—C13—C14 | 0.7 (2) | C23—C24—C25—C20 | −0.9 (3) |
C12—N10—C14—C5 | −178.63 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···O18i | 0.96 | 2.47 | 3.199 (3) | 132 |
C4—H4A···C4ii | 0.96 | 3.01 | 3.584 (2) | 120 |
C16—H16B···O15iii | 0.96 | 3.41 | 3.916 (2) | 115 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z; (iii) −x+1, y+1/2, −z−1/2. |
Experimental details
Crystal data |
Chemical formula | C22H17NO3 |
Mr | 343.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.393 (3), 9.233 (2), 14.162 (3) |
β (°) | 91.81 (3) |
V (Å3) | 1750.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.6 × 0.5 × 0.3 |
|
Data collection |
Diffractometer | Kuma KM-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7169, 5108, 2994 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.705 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.153, 1.03 |
No. of reflections | 5108 |
No. of parameters | 236 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Selected geometric parameters (Å, º) topC2—O15 | 1.361 (2) | O15—C16 | 1.426 (2) |
C9—C11 | 1.406 (2) | C17—O18 | 1.1955 (17) |
C9—C17 | 1.494 (2) | C17—O19 | 1.3474 (19) |
N10—C12 | 1.342 (2) | O19—C20 | 1.4121 (18) |
| | | |
C1—C2—O15 | 125.33 (17) | C17—O19—C20 | 118.74 (11) |
C2—O15—C16 | 117.23 (14) | O18—C17—O19 | 123.33 (14) |
C9—C17—O18 | 126.57 (14) | O19—C20—C21 | 117.90 (14) |
C9—C17—O19 | 110.07 (12) | C20—C21—C26 | 122.10 (16) |
C11—C9—C17 | 120.82 (14) | | |
| | | |
C1—C2—O15—C16 | 0.8 (3) | C11—C9—C17—O19 | 56.37 (18) |
C9—C17—O19—C20 | 174.73 (13) | C17—O19—C20—C21 | −87.90 (18) |
C11—C9—C17—O18 | −125.80 (17) | O19—C20—C21—C26 | 8.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···O18i | 0.96 | 2.47 | 3.199 (3) | 132 |
C4—H4A···C4ii | 0.96 | 3.01 | 3.584 (2) | 120 |
C16—H16B···O15iii | 0.96 | 3.41 | 3.916 (2) | 115 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z; (iii) −x+1, y+1/2, −z−1/2. |
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9-Carboxy-10-methylacridinium phenyl esters constitute the chemiluminogenic fragments of chemiluminescent labels (Rak et al., 1999), which have found numerous applications in immunoassays (Zomer et al., 1991; Dodeigne et al., 2000) and which can potentially be used in environmental, biochemical and medical analyses (Dodeigne et al., 2000). Upon preparation of one such label, we synthesized, as an intermediate product, the title compound, (I), and obtained it in a crystalline form. This prompted us to carry out X-ray measurements in order to determine its structure. Examination of the Cambridge Structural Database (Version?; Allen & Kennard, 1993) shows that this is the first structure containing an acridine-9-carboxylic acid phenyl ester fragment. \sch
The structure (I) is shown in Fig. 1, and selected geometric parameters are given in Table 1. The O and C atoms of the methoxy group lie almost in the plane of the almost planar acridine moiety, while the carboxy group is twisted relative to the acridine skeleton at an angle of 56.8 (5)°. The 2-methylphenyl ester group is twisted from the mean plane of the acridine moiety by 35.9 (5)°. The 2-methylphenyl fragment is almost perpendicular to the plane formed by the atoms of the carboxy group: the angle between the respective mean planes is 87.3 (5)°.
In the crystalline phase, the molecules of (I) are arranged in centrosymmetric pairs, in which they contact through the C4 atoms and the attached H atoms, via a pair of C—H···C contacts, with C···C 3.58 Å, H···C 3.01 Å and C—H···C 119.7° (Fig. 2). These pairs are bonded as a result of nonspecific dispersive interactions, and through a network of C—H···O interactions involving the O18 nonbonded atoms of the carboxy group and the H atoms attached to C6 [H···O 2.475 Å, which is a short C—H···O interaction (Table 2)] and, to some extent, the O15 atoms of the methoxy group and the H atoms attached to C16 from neighbouring molecules [the shortest H···O distance is 3.42 Å, which is a long C—H···O interaction (Table 2)].
The packing in the crystalline phase reveals that the molecules of (I) are arranged regularly and the acridine moieties are situated either parallel or perperdicular to each other; the angles between the respective mean planes are 0.0 (5)° or 84.0 (5)° (Fig. 3).