Dimethyl 2-[(acridin-9-yl)methyl-idene]malonate.

In the title compound, C(19)H(15)NO(4), the acridine system is essentially planar (r.m.s. deviation = 0.015 Å). The crystal packing exhibits π-π inter-actions between pairs of centrosymmetric mol-ecules, one of them between the central heterocyclic rings and others between the outer benzene rings of the acridine systems, with centroid-centroid distances of 3.692 (1) and 3.754 (1) Å, respectively. These pairs are further linked by additional π-π inter-actions along the a-axis direction through one of the two outer benzene ring of neighboring mol-ecules, with a centroid-centroid distance of 3.642 (2) Å.

Related literature

For background to acridines, see: Kumar et al. (2012 ▶). For the biological activity of acridine derivatives, see: Pigatto et al. (2011 ▶); Das et al. (2011 ▶); Kumar et al. (2012 ▶). For the synthesis of acridines, see: Tomar et al. (2010 ▶). For related structures, see: Buckleton & Waters (1984 ▶).

Experimental

Crystal data

C19H15NO4

M = 321.32

Triclinic,

a = 8.3022 (2) Å

b = 9.0208 (3) Å

c = 12.0334 (4) Å

α = 96.468 (2)°

β = 93.652 (2)°

γ = 117.422 (2)°

V = 787.98 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.32 × 0.28 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer

10674 measured reflections

3626 independent reflections

2805 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.148

S = 1.05

3626 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 1997 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000500/lr2094sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000500/lr2094Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000500/lr2094Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H15NO4	Z = 2
Mr = 321.32	F(000) = 336
Triclinic, P1	Dx = 1.354 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3022 (2) Å	Cell parameters from 6418 reflections
b = 9.0208 (3) Å	θ = 2.5–27.5°
c = 12.0334 (4) Å	µ = 0.10 mm−1
α = 96.468 (2)°	T = 295 K
β = 93.652 (2)°	Prism, yellow
γ = 117.422 (2)°	0.32 × 0.28 × 0.22 mm
V = 787.98 (4) Å3

Nonius KappaCCD diffractometer	2805 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.050
Horizonally mounted graphite crystal monochromator	θmax = 27.5°, θmin = 2.6°
Detector resolution: 9 pixels mm-1	h = −10→10
CCD rotation images,thick slices scans	k = −11→10
10674 measured reflections	l = −15→15
3626 independent reflections

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0817P)2 + 0.1056P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3626 reflections	Δρmax = 0.26 e Å−3
218 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.168 (19)

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 > σ(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.

	x	y	z	Uiso*/Ueq
C2	0.18856 (17)	−0.04107 (16)	0.05238 (10)	0.0416 (3)
C8	0.27051 (18)	0.29435 (17)	0.10755 (11)	0.0439 (3)
C1	0.12960 (17)	0.00751 (16)	0.15015 (10)	0.0409 (3)
C16	0.25132 (19)	−0.00447 (18)	0.38809 (12)	0.0475 (3)
N1	0.32779 (16)	0.24918 (14)	0.01345 (9)	0.0477 (3)
C14	0.02296 (18)	−0.12607 (17)	0.21649 (11)	0.0455 (3)
H14	−0.0906	−0.2111	0.1815	0.055*
O4	−0.19557 (15)	−0.38893 (13)	0.31911 (9)	0.0630 (3)
C13	0.16978 (17)	0.17719 (16)	0.17992 (10)	0.0412 (3)
C12	0.11370 (19)	0.24024 (18)	0.27615 (11)	0.0484 (3)
H12	0.0464	0.1665	0.3236	0.058*
C11	0.1572 (2)	0.4058 (2)	0.29913 (12)	0.0544 (4)
H11	0.1202	0.4443	0.3625	0.065*
C6	0.3548 (2)	0.0411 (2)	−0.11100 (12)	0.0549 (4)
H6	0.4194	0.1228	−0.1546	0.066*
C9	0.3139 (2)	0.46746 (18)	0.13512 (13)	0.0538 (4)
H9	0.3808	0.5443	0.0892	0.065*
O2	0.22592 (15)	0.05138 (14)	0.48843 (9)	0.0593 (3)
O1	0.39648 (15)	0.04600 (18)	0.35414 (10)	0.0745 (4)
O3	0.02856 (18)	−0.31220 (15)	0.46082 (10)	0.0716 (4)
C7	0.28933 (18)	0.08723 (17)	−0.01311 (11)	0.0445 (3)
C18	−0.0314 (2)	−0.28576 (17)	0.37642 (11)	0.0488 (3)
C5	0.3247 (2)	−0.1193 (2)	−0.14145 (14)	0.0618 (4)
H5	0.3696	−0.1466	−0.2051	0.074*
C3	0.1592 (2)	−0.20857 (18)	0.01646 (12)	0.0508 (3)
H3	0.0939	−0.2935	0.0577	0.061*
C15	0.07425 (18)	−0.13590 (17)	0.32134 (11)	0.0452 (3)
C10	0.2585 (2)	0.52130 (19)	0.22792 (13)	0.0578 (4)
H10	0.2871	0.6345	0.2449	0.069*
C4	0.2252 (2)	−0.2462 (2)	−0.07701 (14)	0.0588 (4)
H4	0.2048	−0.3563	−0.0989	0.071*
C19	−0.3052 (3)	−0.5404 (2)	0.36533 (18)	0.0765 (5)
H19A	−0.4202	−0.6062	0.3179	0.115*
H19B	−0.3267	−0.5095	0.4398	0.115*
H19C	−0.2415	−0.6059	0.3690	0.115*
C17	0.3884 (3)	0.1685 (3)	0.56385 (16)	0.0767 (5)
H17A	0.3545	0.2006	0.6338	0.115*
H17B	0.4557	0.2672	0.5302	0.115*
H17C	0.4634	0.1156	0.5779	0.115*

	U11	U22	U33	U12	U13	U23
C2	0.0385 (6)	0.0446 (7)	0.0367 (6)	0.0149 (5)	0.0014 (5)	0.0111 (5)
C8	0.0422 (7)	0.0438 (7)	0.0379 (6)	0.0126 (5)	0.0030 (5)	0.0124 (5)
C1	0.0387 (6)	0.0446 (7)	0.0350 (6)	0.0143 (5)	0.0027 (5)	0.0143 (5)
C16	0.0493 (7)	0.0517 (7)	0.0466 (7)	0.0249 (6)	0.0081 (6)	0.0219 (6)
N1	0.0484 (6)	0.0451 (6)	0.0397 (6)	0.0120 (5)	0.0080 (5)	0.0136 (5)
C14	0.0465 (7)	0.0429 (7)	0.0428 (7)	0.0157 (5)	0.0075 (5)	0.0136 (5)
O4	0.0636 (7)	0.0495 (6)	0.0614 (7)	0.0110 (5)	0.0127 (5)	0.0236 (5)
C13	0.0395 (6)	0.0448 (7)	0.0348 (6)	0.0153 (5)	0.0023 (5)	0.0117 (5)
C12	0.0506 (7)	0.0535 (8)	0.0411 (7)	0.0230 (6)	0.0081 (6)	0.0134 (6)
C11	0.0619 (9)	0.0575 (9)	0.0440 (7)	0.0291 (7)	0.0051 (6)	0.0058 (6)
C6	0.0510 (8)	0.0602 (9)	0.0419 (7)	0.0153 (6)	0.0115 (6)	0.0105 (6)
C9	0.0574 (8)	0.0425 (7)	0.0497 (8)	0.0127 (6)	0.0043 (6)	0.0139 (6)
O2	0.0593 (6)	0.0619 (7)	0.0536 (6)	0.0279 (5)	0.0027 (5)	0.0030 (5)
O1	0.0492 (6)	0.1023 (10)	0.0627 (7)	0.0255 (6)	0.0115 (5)	0.0222 (6)
O3	0.0931 (9)	0.0618 (7)	0.0579 (7)	0.0302 (6)	0.0085 (6)	0.0315 (5)
C7	0.0399 (6)	0.0491 (7)	0.0366 (6)	0.0137 (5)	0.0038 (5)	0.0109 (5)
C18	0.0622 (8)	0.0441 (7)	0.0440 (7)	0.0252 (6)	0.0168 (6)	0.0155 (6)
C5	0.0587 (9)	0.0693 (10)	0.0482 (8)	0.0241 (8)	0.0113 (7)	−0.0008 (7)
C3	0.0500 (8)	0.0477 (7)	0.0493 (8)	0.0180 (6)	0.0048 (6)	0.0107 (6)
C15	0.0502 (7)	0.0455 (7)	0.0425 (7)	0.0220 (6)	0.0119 (6)	0.0165 (5)
C10	0.0661 (9)	0.0442 (8)	0.0545 (8)	0.0204 (7)	0.0005 (7)	0.0048 (6)
C4	0.0603 (9)	0.0542 (8)	0.0561 (9)	0.0246 (7)	0.0041 (7)	0.0001 (7)
C19	0.0826 (12)	0.0459 (9)	0.0854 (13)	0.0120 (8)	0.0267 (10)	0.0254 (8)
C17	0.0776 (12)	0.0741 (11)	0.0667 (11)	0.0323 (9)	−0.0107 (9)	−0.0063 (9)

C2—C1	1.4037 (18)	C6—C5	1.351 (2)
C2—C3	1.425 (2)	C6—C7	1.427 (2)
C2—C7	1.4345 (17)	C6—H6	0.9300
C8—N1	1.3482 (18)	C9—C10	1.358 (2)
C8—C9	1.424 (2)	C9—H9	0.9300
C8—C13	1.4356 (17)	O2—C17	1.441 (2)
C1—C13	1.4049 (19)	O3—C18	1.1981 (17)
C1—C14	1.4823 (16)	C18—C15	1.4899 (18)
C16—O1	1.1940 (17)	C5—C4	1.415 (2)
C16—O2	1.3226 (18)	C5—H5	0.9300
C16—C15	1.497 (2)	C3—C4	1.358 (2)
N1—C7	1.3381 (18)	C3—H3	0.9300
C14—C15	1.3315 (18)	C10—H10	0.9300
C14—H14	0.9300	C4—H4	0.9300
O4—C18	1.3293 (19)	C19—H19A	0.9600
O4—C19	1.4474 (18)	C19—H19B	0.9600
C13—C12	1.4301 (19)	C19—H19C	0.9600
C12—C11	1.355 (2)	C17—H17A	0.9600
C12—H12	0.9300	C17—H17B	0.9600
C11—C10	1.419 (2)	C17—H17C	0.9600
C11—H11	0.9300
C1—C2—C3	123.94 (12)	N1—C7—C6	117.91 (12)
C1—C2—C7	117.80 (12)	N1—C7—C2	123.52 (12)
C3—C2—C7	118.24 (12)	C6—C7—C2	118.55 (13)
N1—C8—C9	117.44 (12)	O3—C18—O4	124.20 (13)
N1—C8—C13	123.21 (12)	O3—C18—C15	123.33 (14)
C9—C8—C13	119.35 (12)	O4—C18—C15	112.42 (12)
C2—C1—C13	119.54 (11)	C6—C5—C4	120.40 (14)
C2—C1—C14	117.57 (12)	C6—C5—H5	119.8
C13—C1—C14	122.87 (12)	C4—C5—H5	119.8
O1—C16—O2	124.32 (15)	C4—C3—C2	121.06 (14)
O1—C16—C15	124.28 (14)	C4—C3—H3	119.5
O2—C16—C15	111.38 (11)	C2—C3—H3	119.5
C7—N1—C8	118.15 (11)	C14—C15—C18	122.41 (13)
C15—C14—C1	126.22 (12)	C14—C15—C16	122.17 (11)
C15—C14—H14	116.9	C18—C15—C16	115.18 (11)
C1—C14—H14	116.9	C9—C10—C11	120.38 (14)
C18—O4—C19	115.93 (13)	C9—C10—H10	119.8
C1—C13—C12	124.38 (12)	C11—C10—H10	119.8
C1—C13—C8	117.77 (12)	C3—C4—C5	120.61 (15)
C12—C13—C8	117.83 (12)	C3—C4—H4	119.7
C11—C12—C13	120.94 (13)	C5—C4—H4	119.7
C11—C12—H12	119.5	O4—C19—H19A	109.5
C13—C12—H12	119.5	O4—C19—H19B	109.5
C12—C11—C10	120.94 (14)	H19A—C19—H19B	109.5
C12—C11—H11	119.5	O4—C19—H19C	109.5
C10—C11—H11	119.5	H19A—C19—H19C	109.5
C5—C6—C7	121.14 (14)	H19B—C19—H19C	109.5
C5—C6—H6	119.4	O2—C17—H17A	109.5
C7—C6—H6	119.4	O2—C17—H17B	109.5
C10—C9—C8	120.55 (13)	H17A—C17—H17B	109.5
C10—C9—H9	119.7	O2—C17—H17C	109.5
C8—C9—H9	119.7	H17A—C17—H17C	109.5
C16—O2—C17	116.36 (13)	H17B—C17—H17C	109.5