2-Meth-oxy-9-phenoxy-acridine.

The mol-ecules in the crystal structure of the title compound, C(20)H(15)NO(2), form inversion dimers connected through the C-H⋯N and π-π inter-actions. These dimers are further linked by C-H⋯π inter-actions. The meth-oxy group is nearly coplanar with the acridine ring system [dihedral angle = 4.5 (1)°], whereas the phen-oxy fragment is nearly perpendicular to it [dihedral angle = 85.0 (1)°]. The mean planes of the acridine ring systems are either parallel or inclined at angles of 14.3 (1), 65.4 (1) and 67.3 (1)° in the crystal.

Related literature

For general background to 9-phenoxy­acridines, see: Acheson (1973 ▶); Albert (1966 ▶); Chen et al. (2002 ▶); Demeunynck et al. (2001 ▶); Lebekhov & Samarin (1969 ▶); Ueyama et al. (2002 ▶). For related structures, see: Ebead et al. (2005 ▶); Sikorski et al. (2007 ▶). For inter­molecular inter­actions, see: Hunter et al. (2001 ▶); Mazik et al. (2000 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Acheson (1973 ▶); Chen et al. (2002 ▶); Duprè & Robinson (1945 ▶).

Experimental

Crystal data

C20H15NO2

M = 301.33

Orthorhombic,

a = 8.3042 (2) Å

b = 15.5101 (4) Å

c = 24.0192 (6) Å

V = 3093.65 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.50 × 0.25 × 0.10 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.890, T max = 0.994

56825 measured reflections

2747 independent reflections

2322 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.086

S = 1.10

2747 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.11 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, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008962/ng2741sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008962/ng2741Isup2.hkl

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

C20H15NO2	F(000) = 1264
Mr = 301.33	Dx = 1.294 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 32561 reflections
a = 8.3042 (2) Å	θ = 3.0–29.3°
b = 15.5101 (4) Å	µ = 0.08 mm−1
c = 24.0192 (6) Å	T = 295 K
V = 3093.65 (13) Å3	Plate, light-brown
Z = 8	0.50 × 0.25 × 0.10 mm

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2747 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2322 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −18→18
Tmin = 0.890, Tmax = 0.994	l = −28→28
56825 measured 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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.048P)2 + 0.2828P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2747 reflections	Δρmax = 0.15 e Å−3
210 parameters	Δρmin = −0.11 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: 0.0046 (6)

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.

	x	y	z	Uiso*/Ueq
C1	0.18244 (13)	0.00760 (7)	0.34444 (4)	0.0442 (3)
H1	0.1362	0.0364	0.3145	0.053*
C2	0.26680 (14)	−0.06681 (7)	0.33602 (5)	0.0498 (3)
C3	0.33776 (16)	−0.11161 (8)	0.38157 (5)	0.0560 (3)
H3	0.3938	−0.1626	0.3751	0.067*
C4	0.32483 (15)	−0.08118 (8)	0.43386 (5)	0.0525 (3)
H4	0.3731	−0.1112	0.4629	0.063*
C5	0.13635 (15)	0.12529 (8)	0.56536 (5)	0.0522 (3)
H5	0.1883	0.0946	0.5934	0.063*
C6	0.05228 (16)	0.19741 (9)	0.57843 (5)	0.0591 (3)
H6	0.0471	0.2155	0.6153	0.071*
C7	−0.02759 (15)	0.24540 (8)	0.53666 (5)	0.0573 (3)
H7	−0.0854	0.2945	0.5464	0.069*
C8	−0.02090 (13)	0.22067 (7)	0.48256 (5)	0.0478 (3)
H8	−0.0737	0.2530	0.4555	0.057*
C9	0.08142 (12)	0.11619 (6)	0.41230 (4)	0.0383 (2)
N10	0.23001 (11)	0.02343 (6)	0.49857 (4)	0.0460 (2)
C11	0.16565 (11)	0.04083 (6)	0.39947 (4)	0.0389 (2)
C12	0.23839 (12)	−0.00369 (7)	0.44563 (4)	0.0416 (3)
C13	0.06662 (12)	0.14545 (7)	0.46691 (4)	0.0397 (3)
C14	0.14617 (12)	0.09591 (7)	0.50938 (4)	0.0421 (3)
O15	0.29423 (13)	−0.10503 (6)	0.28557 (3)	0.0676 (3)
C16	0.2364 (2)	−0.06180 (10)	0.23706 (5)	0.0749 (4)
H16A	0.2695	−0.0929	0.2045	0.112*
H16B	0.2799	−0.0045	0.2358	0.112*
H16C	0.1210	−0.0589	0.2382	0.112*
O17	0.02052 (8)	0.16615 (5)	0.36901 (3)	0.0441 (2)
C18	−0.13908 (11)	0.15439 (6)	0.35297 (4)	0.0352 (2)
C19	−0.24472 (13)	0.10027 (6)	0.38029 (4)	0.0410 (3)
H19	−0.2123	0.0697	0.4117	0.049*
C20	−0.40022 (14)	0.09241 (8)	0.35996 (5)	0.0508 (3)
H20	−0.4727	0.0561	0.3779	0.061*
C21	−0.44883 (14)	0.13772 (9)	0.31347 (5)	0.0572 (3)
H21	−0.5530	0.1314	0.2998	0.069*
C22	−0.34193 (15)	0.19255 (9)	0.28733 (5)	0.0552 (3)
H22	−0.3745	0.2235	0.2561	0.066*
C23	−0.18710 (13)	0.20176 (7)	0.30720 (4)	0.0441 (3)
H23	−0.1158	0.2395	0.2900	0.053*

	U11	U22	U33	U12	U13	U23
C1	0.0460 (6)	0.0434 (6)	0.0434 (6)	−0.0019 (5)	−0.0025 (5)	0.0079 (5)
C2	0.0564 (7)	0.0440 (6)	0.0489 (7)	−0.0009 (5)	0.0051 (5)	0.0015 (5)
C3	0.0648 (8)	0.0420 (6)	0.0612 (8)	0.0114 (5)	0.0039 (6)	0.0071 (5)
C4	0.0579 (7)	0.0453 (6)	0.0544 (7)	0.0097 (5)	−0.0032 (5)	0.0141 (5)
C5	0.0596 (7)	0.0521 (7)	0.0450 (6)	−0.0066 (6)	−0.0065 (5)	0.0042 (5)
C6	0.0686 (8)	0.0579 (8)	0.0508 (7)	−0.0073 (6)	0.0007 (6)	−0.0078 (6)
C7	0.0558 (7)	0.0500 (7)	0.0661 (8)	0.0012 (6)	0.0028 (6)	−0.0079 (6)
C8	0.0427 (6)	0.0436 (6)	0.0570 (7)	−0.0004 (5)	−0.0019 (5)	0.0039 (5)
C9	0.0339 (5)	0.0377 (5)	0.0432 (6)	−0.0040 (4)	−0.0049 (4)	0.0119 (4)
N10	0.0487 (5)	0.0440 (5)	0.0452 (5)	0.0003 (4)	−0.0051 (4)	0.0099 (4)
C11	0.0354 (5)	0.0374 (5)	0.0438 (6)	−0.0039 (4)	−0.0014 (4)	0.0091 (4)
C12	0.0405 (5)	0.0401 (6)	0.0442 (6)	−0.0017 (4)	−0.0021 (4)	0.0095 (5)
C13	0.0343 (5)	0.0380 (6)	0.0469 (6)	−0.0058 (4)	−0.0019 (4)	0.0067 (4)
C14	0.0414 (6)	0.0407 (6)	0.0443 (6)	−0.0071 (4)	−0.0030 (4)	0.0068 (5)
O15	0.0937 (7)	0.0575 (5)	0.0515 (5)	0.0130 (5)	0.0051 (5)	−0.0031 (4)
C16	0.1016 (11)	0.0740 (9)	0.0492 (8)	0.0065 (8)	−0.0016 (7)	−0.0043 (7)
O17	0.0378 (4)	0.0443 (4)	0.0502 (4)	−0.0016 (3)	−0.0052 (3)	0.0173 (3)
C18	0.0366 (5)	0.0341 (5)	0.0349 (5)	0.0029 (4)	−0.0004 (4)	−0.0010 (4)
C19	0.0472 (6)	0.0367 (5)	0.0393 (5)	−0.0018 (4)	−0.0032 (4)	0.0043 (4)
C20	0.0470 (6)	0.0497 (7)	0.0556 (7)	−0.0106 (5)	−0.0013 (5)	0.0020 (5)
C21	0.0472 (7)	0.0685 (8)	0.0560 (7)	−0.0050 (6)	−0.0155 (5)	0.0019 (6)
C22	0.0540 (7)	0.0698 (8)	0.0418 (6)	0.0042 (6)	−0.0099 (5)	0.0111 (6)
C23	0.0452 (6)	0.0500 (6)	0.0369 (5)	0.0033 (5)	0.0037 (4)	0.0086 (5)

C1—C2	1.3651 (16)	N10—C12	1.3413 (14)
C1—C11	1.4256 (15)	N10—C14	1.3476 (14)
C1—H1	0.9300	C11—C12	1.4391 (14)
C2—O15	1.3681 (14)	C13—C14	1.4378 (14)
C2—C3	1.4237 (17)	O15—C16	1.4276 (16)
C3—C4	1.3460 (17)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C12	1.4282 (16)	C16—H16C	0.9600
C4—H4	0.9300	O17—C18	1.3922 (12)
C5—C6	1.3554 (19)	C18—C19	1.3801 (14)
C5—C14	1.4220 (16)	C18—C23	1.3812 (14)
C5—H5	0.9300	C19—C20	1.3859 (15)
C6—C7	1.4144 (18)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.3797 (17)
C7—C8	1.3560 (16)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.3805 (18)
C8—C13	1.4250 (16)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.3788 (16)
C9—O17	1.3920 (12)	C22—H22	0.9300
C9—C13	1.3934 (14)	C23—H23	0.9300
C9—C11	1.3965 (15)
C2—C1—C11	119.54 (10)	C4—C12—C11	117.54 (10)
C2—C1—H1	120.2	C9—C13—C8	124.06 (9)
C11—C1—H1	120.2	C9—C13—C14	116.95 (9)
C1—C2—O15	125.66 (10)	C8—C13—C14	118.99 (10)
C1—C2—C3	120.75 (11)	N10—C14—C5	118.62 (10)
O15—C2—C3	113.59 (10)	N10—C14—C13	123.13 (10)
C4—C3—C2	120.85 (11)	C5—C14—C13	118.25 (10)
C4—C3—H3	119.6	C2—O15—C16	117.61 (10)
C2—C3—H3	119.6	O15—C16—H16A	109.5
C3—C4—C12	121.32 (10)	O15—C16—H16B	109.5
C3—C4—H4	119.3	H16A—C16—H16B	109.5
C12—C4—H4	119.3	O15—C16—H16C	109.5
C6—C5—C14	120.86 (11)	H16A—C16—H16C	109.5
C6—C5—H5	119.6	H16B—C16—H16C	109.5
C14—C5—H5	119.6	C9—O17—C18	118.66 (7)
C5—C6—C7	120.77 (11)	C19—C18—C23	121.24 (9)
C5—C6—H6	119.6	C19—C18—O17	123.59 (9)
C7—C6—H6	119.6	C23—C18—O17	115.17 (9)
C8—C7—C6	120.77 (12)	C18—C19—C20	118.57 (10)
C8—C7—H7	119.6	C18—C19—H19	120.7
C6—C7—H7	119.6	C20—C19—H19	120.7
C7—C8—C13	120.35 (11)	C21—C20—C19	120.86 (11)
C7—C8—H8	119.8	C21—C20—H20	119.6
C13—C8—H8	119.8	C19—C20—H20	119.6
O17—C9—C13	119.33 (9)	C20—C21—C22	119.58 (11)
O17—C9—C11	118.88 (9)	C20—C21—H21	120.2
C13—C9—C11	121.64 (9)	C22—C21—H21	120.2
C12—N10—C14	118.10 (9)	C23—C22—C21	120.40 (10)
C9—C11—C1	123.79 (9)	C23—C22—H22	119.8
C9—C11—C12	116.22 (9)	C21—C22—H22	119.8
C1—C11—C12	119.99 (9)	C22—C23—C18	119.31 (10)
N10—C12—C4	118.53 (9)	C22—C23—H23	120.3
N10—C12—C11	123.94 (10)	C18—C23—H23	120.3
C11—C1—C2—O15	−178.96 (10)	C11—C9—C13—C14	1.82 (14)
C11—C1—C2—C3	0.15 (17)	C7—C8—C13—C9	−179.10 (10)
C1—C2—C3—C4	−0.73 (19)	C7—C8—C13—C14	0.59 (16)
O15—C2—C3—C4	178.49 (11)	C12—N10—C14—C5	179.97 (9)
C2—C3—C4—C12	0.68 (19)	C12—N10—C14—C13	−0.39 (15)
C14—C5—C6—C7	−0.13 (19)	C6—C5—C14—N10	−179.41 (11)
C5—C6—C7—C8	−0.47 (19)	C6—C5—C14—C13	0.93 (17)
C6—C7—C8—C13	0.22 (18)	C9—C13—C14—N10	−1.08 (14)
O17—C9—C11—C1	−5.34 (14)	C8—C13—C14—N10	179.21 (9)
C13—C9—C11—C1	179.14 (9)	C9—C13—C14—C5	178.57 (9)
O17—C9—C11—C12	174.41 (8)	C8—C13—C14—C5	−1.14 (14)
C13—C9—C11—C12	−1.11 (14)	C1—C2—O15—C16	3.06 (18)
C2—C1—C11—C9	−179.81 (10)	C3—C2—O15—C16	−176.11 (12)
C2—C1—C11—C12	0.45 (15)	C13—C9—O17—C18	−88.82 (11)
C14—N10—C12—C4	−179.03 (10)	C11—C9—O17—C18	95.56 (11)
C14—N10—C12—C11	1.18 (15)	C9—O17—C18—C19	4.98 (14)
C3—C4—C12—N10	−179.88 (11)	C9—O17—C18—C23	−175.51 (9)
C3—C4—C12—C11	−0.07 (17)	C23—C18—C19—C20	1.71 (16)
C9—C11—C12—N10	−0.46 (15)	O17—C18—C19—C20	−178.82 (9)
C1—C11—C12—N10	179.31 (10)	C18—C19—C20—C21	−0.10 (17)
C9—C11—C12—C4	179.75 (9)	C19—C20—C21—C22	−0.95 (19)
C1—C11—C12—C4	−0.49 (15)	C20—C21—C22—C23	0.4 (2)
O17—C9—C13—C8	6.01 (15)	C21—C22—C23—C18	1.14 (18)
C11—C9—C13—C8	−178.49 (9)	C19—C18—C23—C22	−2.23 (16)
O17—C9—C13—C14	−173.68 (8)	O17—C18—C23—C22	178.25 (10)

Cg2 and Cg4 are 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
C19—H19···N10i	0.93	2.60	3.487 (2)	160
C6—H6···Cg4ii	0.93	2.80	3.459 (2)	129
C16—H16B···Cg4iii	0.96	2.94	3.658 (2)	133
C20—H20···Cg2iv	0.93	2.71	3.576 (2)	156

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	1i	3.984 (1)	0.0	3.569 (1)	1.770 (1)
2	3i	3.932 (1)	1.6	3.564 (1)	1.661 (1)
3	2i	3.932 (1)	1.6	3.541 (1)	1.707 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are 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
C19—H19⋯N10i	0.93	2.60	3.487 (2)	160
C6—H6⋯Cg4ii	0.93	2.80	3.459 (2)	129
C16—H16B⋯Cg4iii	0.96	2.94	3.658 (2)	133
C20—H20⋯Cg2iv	0.93	2.71	3.576 (2)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Table 2

π–π inter­actions (Å,°)

Cg1, Cg2 and Cg3 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12 and C5–C8/C13/C14 rings, respectively. CgI⋯CgJ is the distance between ring centroids. The dihedral angle is that between the planes of the rings I and J. CgI_Perp is the perpendicular distance of CgI from ring J. CgI_Offset is the distance between CgI and the perpendicular projection of CgJ on ring I.

I	J	CgI⋯CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	1i	3.984 (1)	0.0	3.569 (1)	1.770 (1)
2	3i	3.932 (1)	1.6	3.564 (1)	1.661 (1)
3	2i	3.932 (1)	1.6	3.541 (1)	1.707 (1)

Symmetry code: (i) –x, –y, –z + 1.