Phenyl acridine-9-carboxyl-ate.

The acridine ring system and the benzene ring in the title compound, C(20)H(13)NO(2), are oriented at a dihedral angle of 6.4 (2)°. The carboxyl group is twisted at an angle of 83.6 (2)° relative to the acridine skeleton. The mol-ecules in the crystal are arranged in stacks along the b axis, with two of the acridine rings involved in multiple π-π inter-actions [centroid-centroid distances in the range 3.536 (2)-3.894 (2) Å]. Stacks arranged parallel are linked via C-H⋯π inter-actions, forming layers in the ac plane that are in contact with adjacent, inversely oriented layers via other C-H⋯π inter-actions, giving rise to double layers. The inversely oriented double layers inter-act dispersively. The acridine units are parallel within the parallel-oriented stacks, but inclined at an angle of 79.6 (2)° in the inversely oriented stacks.

Related literature

For general background to the applications of the title compound, see: Krzymiński et al. (2011 ▶); Natrajan et al. (2012 ▶); Trzybiński et al. (2010 ▶). For related structures, see: Trzybiński et al. (2013 ▶). For inter­molecular inter­actions, see: Hunter et al. (2001 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Sato (1996 ▶); Trzybiński et al. (2010 ▶).

Experimental

Crystal data

C20H13NO2

M = 299.31

Monoclinic,

a = 17.094 (2) Å

b = 5.4175 (7) Å

c = 16.310 (2) Å

β = 95.545 (11)°

V = 1503.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.6 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.354, T max = 0.986

9221 measured reflections

2651 independent reflections

1560 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.203

S = 1.04

2651 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data 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, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002055/xu5671sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002055/xu5671Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002055/xu5671Isup3.cml

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

C20H13NO2	F(000) = 624
Mr = 299.31	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2651 reflections
a = 17.094 (2) Å	θ = 3.3–25.0°
b = 5.4175 (7) Å	µ = 0.09 mm−1
c = 16.310 (2) Å	T = 295 K
β = 95.545 (11)°	Needle, pale-yellow
V = 1503.3 (3) Å3	0.6 × 0.2 × 0.1 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2651 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	1560 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
Detector resolution: 10.4002 pixels mm-1	θmax = 25.0°, θmin = 3.3°
ω scans	h = −17→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −5→6
Tmin = 0.354, Tmax = 0.986	l = −16→19
9221 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1073P)2] where P = (Fo2 + 2Fc2)/3
2651 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.15883 (16)	−0.0807 (5)	0.28634 (16)	0.0564 (7)
H1	0.2005	−0.0842	0.2537	0.068*
C2	0.09977 (17)	−0.2461 (5)	0.27301 (17)	0.0602 (8)
H2	0.1012	−0.3623	0.2312	0.072*
C3	0.03597 (17)	−0.2442 (5)	0.32180 (18)	0.0622 (8)
H3	−0.0042	−0.3592	0.3118	0.075*
C4	0.03260 (16)	−0.0781 (5)	0.38254 (17)	0.0573 (7)
H4	−0.0098	−0.0801	0.4142	0.069*
C5	0.13817 (18)	0.5964 (5)	0.54258 (17)	0.0621 (8)
H5	0.0945	0.5900	0.5724	0.075*
C6	0.1938 (2)	0.7688 (5)	0.56161 (18)	0.0690 (8)
H6	0.1877	0.8807	0.6038	0.083*
C7	0.26132 (19)	0.7811 (5)	0.51795 (19)	0.0673 (8)
H7	0.2996	0.9000	0.5318	0.081*
C8	0.27029 (17)	0.6208 (5)	0.45642 (17)	0.0581 (7)
H8	0.3149	0.6312	0.4281	0.070*
C9	0.21784 (14)	0.2683 (4)	0.36980 (15)	0.0473 (7)
N10	0.08713 (13)	0.2595 (4)	0.46103 (13)	0.0548 (6)
C11	0.15783 (14)	0.0982 (4)	0.34973 (15)	0.0451 (6)
C12	0.09280 (15)	0.1001 (4)	0.39897 (15)	0.0489 (7)
C13	0.21349 (14)	0.4373 (4)	0.43382 (15)	0.0479 (7)
C14	0.14481 (15)	0.4254 (4)	0.47830 (15)	0.0506 (7)
C15	0.29032 (16)	0.2631 (5)	0.32487 (17)	0.0552 (7)
O16	0.28060 (10)	0.3857 (3)	0.25400 (11)	0.0581 (6)
O17	0.34884 (13)	0.1610 (5)	0.34906 (14)	0.1104 (10)
C18	0.34637 (15)	0.3952 (5)	0.20676 (15)	0.0486 (7)
C19	0.39837 (17)	0.5859 (5)	0.21985 (17)	0.0603 (8)
H19	0.3919	0.7045	0.2599	0.072*
C20	0.46112 (17)	0.5984 (6)	0.1720 (2)	0.0695 (9)
H20	0.4975	0.7259	0.1801	0.083*
C21	0.46958 (17)	0.4238 (6)	0.11312 (19)	0.0695 (9)
H21	0.5119	0.4321	0.0814	0.083*
C22	0.41592 (19)	0.2364 (6)	0.10059 (19)	0.0699 (9)
H22	0.4216	0.1193	0.0599	0.084*
C23	0.35334 (17)	0.2201 (5)	0.14809 (18)	0.0613 (8)
H23	0.3169	0.0927	0.1401	0.074*

	U11	U22	U33	U12	U13	U23
C1	0.0505 (18)	0.0670 (17)	0.0530 (16)	0.0065 (13)	0.0117 (13)	0.0049 (14)
C2	0.060 (2)	0.0634 (17)	0.0577 (17)	0.0004 (14)	0.0095 (14)	−0.0044 (14)
C3	0.0557 (19)	0.0651 (17)	0.0657 (19)	−0.0119 (13)	0.0046 (15)	0.0053 (16)
C4	0.0440 (17)	0.0697 (17)	0.0600 (17)	−0.0022 (13)	0.0151 (13)	0.0072 (15)
C5	0.065 (2)	0.0662 (17)	0.0579 (17)	0.0055 (15)	0.0196 (14)	−0.0019 (15)
C6	0.083 (2)	0.0668 (18)	0.0567 (18)	0.0026 (16)	0.0038 (16)	−0.0074 (15)
C7	0.071 (2)	0.0649 (18)	0.0643 (19)	−0.0087 (15)	−0.0035 (16)	0.0059 (16)
C8	0.0508 (18)	0.0667 (17)	0.0565 (17)	−0.0039 (13)	0.0045 (13)	0.0079 (14)
C9	0.0397 (15)	0.0578 (15)	0.0460 (14)	0.0069 (11)	0.0123 (11)	0.0092 (12)
N10	0.0488 (15)	0.0625 (13)	0.0561 (14)	−0.0013 (11)	0.0202 (11)	0.0040 (11)
C11	0.0348 (14)	0.0565 (14)	0.0453 (14)	0.0046 (11)	0.0111 (11)	0.0059 (13)
C12	0.0427 (16)	0.0568 (15)	0.0479 (15)	0.0019 (12)	0.0081 (12)	0.0084 (13)
C13	0.0415 (16)	0.0553 (15)	0.0477 (15)	0.0028 (11)	0.0077 (12)	0.0083 (12)
C14	0.0478 (17)	0.0557 (15)	0.0496 (15)	0.0049 (12)	0.0108 (12)	0.0071 (13)
C15	0.0421 (17)	0.0687 (17)	0.0564 (17)	0.0071 (13)	0.0132 (13)	0.0141 (14)
O16	0.0396 (11)	0.0788 (12)	0.0590 (11)	0.0076 (8)	0.0204 (8)	0.0163 (10)
O17	0.0564 (16)	0.182 (2)	0.0990 (18)	0.0486 (15)	0.0378 (13)	0.0715 (17)
C18	0.0376 (15)	0.0609 (15)	0.0493 (15)	0.0022 (12)	0.0140 (11)	0.0099 (13)
C19	0.0558 (18)	0.0657 (17)	0.0615 (17)	−0.0029 (14)	0.0169 (14)	−0.0034 (14)
C20	0.051 (2)	0.0773 (19)	0.082 (2)	−0.0141 (14)	0.0167 (16)	0.0079 (18)
C21	0.0485 (19)	0.096 (2)	0.0667 (19)	0.0011 (16)	0.0220 (15)	0.0150 (18)
C22	0.071 (2)	0.080 (2)	0.0629 (19)	0.0036 (16)	0.0253 (16)	−0.0085 (16)
C23	0.0560 (19)	0.0645 (17)	0.0662 (18)	−0.0090 (13)	0.0193 (14)	−0.0021 (15)

C1—C2	1.352 (4)	C9—C15	1.500 (4)
C1—C11	1.418 (3)	N10—C12	1.341 (3)
C1—H1	0.9300	N10—C14	1.344 (3)
C2—C3	1.411 (4)	C11—C12	1.433 (3)
C2—H2	0.9300	C13—C14	1.440 (3)
C3—C4	1.343 (4)	C15—O17	1.177 (3)
C3—H3	0.9300	C15—O16	1.329 (3)
C4—C12	1.418 (4)	O16—C18	1.424 (3)
C4—H4	0.9300	C18—C23	1.361 (4)
C5—C6	1.347 (4)	C18—C19	1.366 (4)
C5—C14	1.412 (3)	C19—C20	1.387 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.415 (4)	C20—C21	1.366 (4)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.347 (4)	C21—C22	1.370 (4)
C7—H7	0.9300	C21—H21	0.9300
C8—C13	1.413 (4)	C22—C23	1.383 (4)
C8—H8	0.9300	C22—H22	0.9300
C9—C11	1.394 (3)	C23—H23	0.9300
C9—C13	1.396 (3)
C2—C1—C11	120.6 (3)	N10—C12—C4	118.5 (2)
C2—C1—H1	119.7	N10—C12—C11	123.0 (2)
C11—C1—H1	119.7	C4—C12—C11	118.5 (2)
C1—C2—C3	120.7 (3)	C9—C13—C8	124.9 (2)
C1—C2—H2	119.6	C9—C13—C14	116.9 (2)
C3—C2—H2	119.6	C8—C13—C14	118.2 (2)
C4—C3—C2	120.8 (3)	N10—C14—C5	119.0 (2)
C4—C3—H3	119.6	N10—C14—C13	122.8 (2)
C2—C3—H3	119.6	C5—C14—C13	118.2 (2)
C3—C4—C12	120.9 (3)	O17—C15—O16	123.8 (2)
C3—C4—H4	119.6	O17—C15—C9	124.1 (2)
C12—C4—H4	119.6	O16—C15—C9	112.1 (2)
C6—C5—C14	121.4 (3)	C15—O16—C18	116.72 (19)
C6—C5—H5	119.3	C23—C18—C19	122.5 (2)
C14—C5—H5	119.3	C23—C18—O16	118.9 (2)
C5—C6—C7	120.5 (3)	C19—C18—O16	118.6 (2)
C5—C6—H6	119.7	C18—C19—C20	118.4 (3)
C7—C6—H6	119.7	C18—C19—H19	120.8
C8—C7—C6	120.1 (3)	C20—C19—H19	120.8
C8—C7—H7	119.9	C21—C20—C19	120.1 (3)
C6—C7—H7	119.9	C21—C20—H20	119.9
C7—C8—C13	121.5 (3)	C19—C20—H20	119.9
C7—C8—H8	119.2	C20—C21—C22	120.2 (3)
C13—C8—H8	119.2	C20—C21—H21	119.9
C11—C9—C13	121.2 (2)	C22—C21—H21	119.9
C11—C9—C15	119.8 (2)	C21—C22—C23	120.4 (3)
C13—C9—C15	118.9 (2)	C21—C22—H22	119.8
C12—N10—C14	118.9 (2)	C23—C22—H22	119.8
C9—C11—C1	124.2 (2)	C18—C23—C22	118.3 (3)
C9—C11—C12	117.2 (2)	C18—C23—H23	120.8
C1—C11—C12	118.6 (2)	C22—C23—H23	120.8
C11—C1—C2—C3	0.0 (4)	C7—C8—C13—C14	0.2 (4)
C1—C2—C3—C4	0.0 (4)	C12—N10—C14—C5	178.8 (2)
C2—C3—C4—C12	0.3 (4)	C12—N10—C14—C13	−1.1 (4)
C14—C5—C6—C7	−0.8 (4)	C6—C5—C14—N10	−179.0 (3)
C5—C6—C7—C8	0.4 (4)	C6—C5—C14—C13	0.8 (4)
C6—C7—C8—C13	−0.2 (4)	C9—C13—C14—N10	0.8 (4)
C13—C9—C11—C1	−179.1 (2)	C8—C13—C14—N10	179.3 (2)
C15—C9—C11—C1	−2.1 (4)	C9—C13—C14—C5	−179.1 (2)
C13—C9—C11—C12	−1.7 (3)	C8—C13—C14—C5	−0.5 (3)
C15—C9—C11—C12	175.4 (2)	C11—C9—C15—O17	−95.7 (4)
C2—C1—C11—C9	177.2 (2)	C13—C9—C15—O17	81.4 (4)
C2—C1—C11—C12	−0.2 (4)	C11—C9—C15—O16	83.7 (3)
C14—N10—C12—C4	178.5 (2)	C13—C9—C15—O16	−99.2 (3)
C14—N10—C12—C11	−0.1 (3)	O17—C15—O16—C18	−1.4 (4)
C3—C4—C12—N10	−179.1 (2)	C9—C15—O16—C18	179.2 (2)
C3—C4—C12—C11	−0.5 (4)	C15—O16—C18—C23	92.5 (3)
C9—C11—C12—N10	1.4 (4)	C15—O16—C18—C19	−90.1 (3)
C1—C11—C12—N10	179.0 (2)	C23—C18—C19—C20	−0.9 (4)
C9—C11—C12—C4	−177.1 (2)	O16—C18—C19—C20	−178.2 (2)
C1—C11—C12—C4	0.4 (3)	C18—C19—C20—C21	0.5 (4)
C11—C9—C13—C8	−177.8 (2)	C19—C20—C21—C22	0.4 (4)
C15—C9—C13—C8	5.1 (4)	C20—C21—C22—C23	−0.9 (5)
C11—C9—C13—C14	0.6 (3)	C19—C18—C23—C22	0.5 (4)
C15—C9—C13—C14	−176.4 (2)	O16—C18—C23—C22	177.7 (2)
C7—C8—C13—C9	178.6 (2)	C21—C22—C23—C18	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg2i	0.93	2.98	3.712 (3)	137
C7—H7···Cg4ii	0.93	2.84	3.646 (3)	145

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	2iii	3.894 (2)	1.7 (2)	3.451 (1)	1.804 (1)
1	3iv	3.893 (2)	1.4 (2)	3.454 (1)	1.796 (1)
2	1iv	3.894 (2)	1.7 (2)	3.498 (2)	1.711 (2)
2	3iv	3.536 (2)	1.1 (2)	3.482 (2)	0.616 (2)
3	1iii	3.893 (2)	1.4 (2)	3.496 (2)	1.713 (2)
3	2iii	3.536 (2)	1.1 (2)	3.481 (2)	0.621 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 denote the centroids of the C1–C4/C11/C12 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg2i	0.93	2.98	3.712 (3)	137
C7—H7⋯Cg4ii	0.93	2.84	3.646 (3)	145

Symmetry codes: (i) ; (ii) .