9-Benzyl­acridine

In the crystal structure of the title compound, C₂₀H₁₅N, mol­ecules related by a centre of symmetry are arranged in pairs that are stabilized via π–π inter­actions between the acridine units. Adjacent pairs, with the acridine ring systems arranged in a herringbone pattern, are linked through a network of C—H...π inter­actions. Non-specific dispersive inter­actions between layers formed from pairs in the ab plane stabilize the crystal structure. The acridine ring systems in pairs are parallel, while in adjacent pairs they are inclined to each other at 78.3 (2)°. The acridine systems and phenyl ring are oriented at 73.3 (2)° to each other.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.039
• wR factor = 0.110
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Computing details

Data collection: KM-4 Software (Oxford Diffraction, 2003); 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 and PLATON (Spek, 2003).

9-benzylacridine

Crystal data

C20H15N	F(000) = 568
Mr = 269.33	Dx = 1.253 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 50 reflections
a = 10.713 (2) Å	θ = 2.2–25.0°
b = 10.605 (2) Å	µ = 0.07 mm^−1
c = 13.033 (3) Å	T = 290 K
β = 105.33 (3)°	Prism, yellow
V = 1428.0 (5) Å^3	0.4 × 0.3 × 0.2 mm
Z = 4

Data collection

Kuma KM-4 diffractometer	Rint = 0.018
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.2°
Graphite monochromator	h = −12→12
θ/2θ scans	k = 0→12
2634 measured reflections	l = 0→15
2517 independent reflections	3 standard reflections every 200 reflections
1598 reflections with I > 2σ(I)	intensity decay: 1.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 0.2074P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2517 reflections	Δρmax = 0.14 e Å^−3
191 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.047 (3)

Special details

Experimental. ¹H NMR analysis (Medium?, δ, p.p.m.): 5.05 (s, 2H), 7.25 (m, 5H), 7.56 (t, 2H), 7.82 (t, 2H), 8.26 (d, 2H), 8.36 (d, 2H).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.13489 (17)	0.10962 (18)	−0.04479 (14)	0.0534 (5)
H1	0.1974	0.0651	−0.0677	0.064*
C2	0.04996 (19)	0.18262 (19)	−0.11449 (15)	0.0627 (5)
H2	0.0548	0.1878	−0.1846	0.075*
C3	−0.04571 (19)	0.25100 (18)	−0.08280 (16)	0.0639 (5)
H3	−0.1038	0.3007	−0.1320	0.077*
C4	−0.05395 (16)	0.24506 (16)	0.01836 (14)	0.0546 (5)
H4	−0.1171	0.2916	0.0386	0.065*
C5	0.07839 (17)	0.08758 (18)	0.36860 (14)	0.0540 (5)
H5	0.0126	0.1349	0.3842	0.065*
C6	0.1547 (2)	0.01478 (19)	0.44482 (15)	0.0629 (5)
H6	0.1403	0.0114	0.5121	0.075*
C7	0.25531 (19)	−0.05561 (19)	0.42342 (15)	0.0627 (5)
H7	0.3074	−0.1051	0.4767	0.075*
C8	0.27751 (16)	−0.05246 (17)	0.32647 (14)	0.0530 (5)
H8	0.3454	−0.0994	0.3142	0.064*
C9	0.21673 (13)	0.02557 (14)	0.13961 (13)	0.0397 (4)
N10	0.01732 (12)	0.16626 (12)	0.19327 (11)	0.0438 (4)
C11	0.13093 (14)	0.09918 (15)	0.06346 (12)	0.0405 (4)
C12	0.03265 (14)	0.16853 (14)	0.09458 (13)	0.0418 (4)
C13	0.19950 (14)	0.02100 (14)	0.24258 (13)	0.0400 (4)
C14	0.09738 (14)	0.09277 (14)	0.26528 (12)	0.0404 (4)
C15	0.32503 (15)	−0.04720 (15)	0.11307 (14)	0.0482 (4)
H15A	0.3013	−0.0650	0.0374	0.058*
H15B	0.3350	−0.1272	0.1504	0.058*
C16	0.45310 (15)	0.02115 (15)	0.14188 (13)	0.0438 (4)
C17	0.56229 (17)	−0.03642 (19)	0.20470 (15)	0.0595 (5)
H17	0.5560	−0.1168	0.2315	0.071*
C18	0.68034 (18)	0.0236 (2)	0.22815 (17)	0.0705 (6)
H18	0.7527	−0.0163	0.2711	0.085*
C19	0.69247 (18)	0.1415 (2)	0.18893 (16)	0.0679 (6)
H19	0.7726	0.1814	0.2041	0.081*
C20	0.58462 (19)	0.1995 (2)	0.12703 (16)	0.0654 (5)
H20	0.5914	0.2797	0.1002	0.078*
C21	0.46605 (17)	0.14022 (18)	0.10410 (15)	0.0562 (5)
H21	0.3936	0.1814	0.0624	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0529 (10)	0.0579 (11)	0.0501 (11)	−0.0109 (9)	0.0151 (8)	−0.0069 (9)
C2	0.0691 (12)	0.0675 (13)	0.0463 (11)	−0.0190 (10)	0.0060 (9)	0.0034 (10)
C3	0.0621 (12)	0.0571 (12)	0.0598 (12)	−0.0061 (10)	−0.0063 (9)	0.0103 (10)
C4	0.0463 (9)	0.0489 (10)	0.0613 (12)	0.0016 (8)	0.0016 (8)	0.0017 (9)
C5	0.0564 (11)	0.0551 (11)	0.0557 (11)	0.0025 (9)	0.0236 (9)	−0.0026 (9)
C6	0.0756 (13)	0.0660 (12)	0.0504 (11)	−0.0017 (11)	0.0227 (10)	0.0040 (10)
C7	0.0680 (12)	0.0598 (12)	0.0573 (12)	0.0071 (10)	0.0115 (10)	0.0153 (9)
C8	0.0466 (10)	0.0482 (10)	0.0644 (11)	0.0075 (8)	0.0148 (8)	0.0078 (8)
C9	0.0339 (8)	0.0343 (8)	0.0519 (10)	−0.0058 (7)	0.0130 (7)	−0.0076 (7)
N10	0.0365 (7)	0.0414 (8)	0.0529 (9)	0.0022 (6)	0.0108 (6)	−0.0037 (6)
C11	0.0366 (8)	0.0388 (8)	0.0454 (9)	−0.0095 (7)	0.0098 (7)	−0.0060 (7)
C12	0.0343 (8)	0.0380 (9)	0.0499 (10)	−0.0048 (7)	0.0055 (7)	−0.0027 (7)
C13	0.0350 (8)	0.0339 (8)	0.0504 (9)	−0.0032 (7)	0.0097 (7)	−0.0030 (7)
C14	0.0358 (8)	0.0377 (8)	0.0477 (9)	−0.0035 (7)	0.0112 (7)	−0.0047 (7)
C15	0.0456 (9)	0.0428 (9)	0.0597 (11)	0.0007 (7)	0.0202 (8)	−0.0070 (8)
C16	0.0411 (8)	0.0472 (9)	0.0482 (9)	0.0029 (8)	0.0207 (7)	−0.0056 (8)
C17	0.0491 (10)	0.0627 (11)	0.0678 (12)	0.0073 (9)	0.0175 (9)	0.0067 (10)
C18	0.0436 (10)	0.0929 (16)	0.0719 (13)	0.0096 (11)	0.0096 (9)	0.0021 (12)
C19	0.0445 (10)	0.0944 (17)	0.0697 (13)	−0.0148 (11)	0.0236 (10)	−0.0175 (12)
C20	0.0641 (12)	0.0664 (12)	0.0710 (13)	−0.0146 (10)	0.0273 (10)	0.0044 (11)
C21	0.0482 (10)	0.0582 (11)	0.0624 (12)	−0.0010 (9)	0.0151 (8)	0.0070 (9)

Geometric parameters (Å, º)

C1—C2	1.347 (3)	C9—C15	1.508 (2)
C1—C11	1.427 (2)	N10—C12	1.339 (2)
C1—H1	0.9300	N10—C14	1.341 (2)
C2—C3	1.404 (3)	C11—C12	1.428 (2)
C2—H2	0.9300	C13—C14	1.426 (2)
C3—C4	1.346 (3)	C15—C16	1.509 (2)
C3—H3	0.9300	C15—H15A	0.9700
C4—C12	1.421 (2)	C15—H15B	0.9700
C4—H4	0.9300	C16—C21	1.376 (2)
C5—C6	1.350 (3)	C16—C17	1.380 (2)
C5—C14	1.415 (2)	C17—C18	1.376 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.398 (3)	C18—C19	1.370 (3)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.346 (3)	C19—C20	1.368 (3)
C7—H7	0.9300	C19—H19	0.9300
C8—C13	1.420 (2)	C20—C21	1.377 (3)
C8—H8	0.9300	C20—H20	0.9300
C9—C11	1.399 (2)	C21—H21	0.9300
C9—C13	1.403 (2)
C2—C1—C11	121.32 (18)	N10—C12—C4	117.29 (15)
C2—C1—H1	119.3	N10—C12—C11	123.39 (14)
C11—C1—H1	119.3	C4—C12—C11	119.32 (15)
C1—C2—C3	120.93 (18)	C9—C13—C8	123.77 (15)
C1—C2—H2	119.5	C9—C13—C14	118.82 (14)
C3—C2—H2	119.5	C8—C13—C14	117.41 (15)
C4—C3—C2	120.40 (18)	N10—C14—C5	117.54 (14)
C4—C3—H3	119.8	N10—C14—C13	123.27 (14)
C2—C3—H3	119.8	C5—C14—C13	119.19 (15)
C3—C4—C12	120.78 (18)	C9—C15—H15A	108.8
C3—C4—H4	119.6	C16—C15—H15A	108.8
C12—C4—H4	119.6	C9—C15—H15B	108.8
C6—C5—C14	120.73 (17)	C16—C15—H15B	108.8
C6—C5—H5	119.6	H15A—C15—H15B	107.7
C14—C5—H5	119.6	C21—C16—C17	117.94 (16)
C5—C6—C7	120.49 (17)	C21—C16—C15	121.54 (15)
C5—C6—H6	119.8	C17—C16—C15	120.49 (16)
C7—C6—H6	119.8	C18—C17—C16	120.79 (19)
C8—C7—C6	120.70 (18)	C18—C17—H17	119.6
C8—C7—H7	119.6	C16—C17—H17	119.6
C6—C7—H7	119.6	C19—C18—C17	120.78 (19)
C7—C8—C13	121.47 (17)	C19—C18—H18	119.6
C7—C8—H8	119.3	C17—C18—H18	119.6
C13—C8—H8	119.3	C20—C19—C18	118.79 (18)
C11—C9—C13	118.03 (14)	C20—C19—H19	120.6
C9—C15—C16	113.66 (13)	C18—C19—H19	120.6
C11—C9—C15	121.60 (15)	C19—C20—C21	120.64 (19)
C13—C9—C15	120.37 (15)	C19—C20—H20	119.7
C12—N10—C14	117.67 (13)	C21—C20—H20	119.7
C9—C11—C1	123.99 (15)	C16—C21—C20	121.05 (18)
C9—C11—C12	118.77 (14)	C16—C21—H21	119.5
C1—C11—C12	117.24 (15)	C20—C21—H21	119.5
C11—C1—C2—C3	−0.1 (3)	C15—C9—C13—C14	178.94 (13)
C1—C2—C3—C4	0.2 (3)	C7—C8—C13—C9	−178.62 (17)
C2—C3—C4—C12	−0.8 (3)	C7—C8—C13—C14	0.7 (2)
C14—C5—C6—C7	0.9 (3)	C12—N10—C14—C5	−178.11 (14)
C5—C6—C7—C8	−0.3 (3)	C12—N10—C14—C13	2.1 (2)
C6—C7—C8—C13	−0.6 (3)	C6—C5—C14—N10	179.47 (16)
C13—C9—C11—C1	−178.20 (14)	C6—C5—C14—C13	−0.7 (3)
C1—C11—C9—C15	1.8 (2)	C9—C13—C14—N10	−0.9 (2)
C13—C9—C11—C12	1.7 (2)	C8—C13—C14—N10	179.72 (14)
C15—C9—C11—C12	−178.29 (13)	C9—C13—C14—C5	179.29 (15)
C2—C1—C11—C9	−179.66 (16)	C8—C13—C14—C5	−0.1 (2)
C2—C1—C11—C12	0.5 (2)	C9—C15—C16—C17	126.50 (17)
C14—N10—C12—C4	179.01 (14)	C11—C9—C15—C16	96.03 (18)
C14—N10—C12—C11	−1.4 (2)	C13—C9—C15—C16	−83.94 (18)
C3—C4—C12—N10	−179.16 (16)	C9—C15—C16—C21	−55.6 (2)
C3—C4—C12—C11	1.2 (2)	C21—C16—C17—C18	−0.3 (3)
C9—C11—C12—N10	−0.5 (2)	C15—C16—C17—C18	177.67 (17)
C1—C11—C12—N10	179.37 (14)	C16—C17—C18—C19	−0.6 (3)
C9—C11—C12—C4	179.11 (14)	C17—C18—C19—C20	0.9 (3)
C1—C11—C12—C4	−1.0 (2)	C18—C19—C20—C21	−0.3 (3)
C11—C9—C13—C8	178.32 (14)	C17—C16—C21—C20	0.9 (3)
C15—C9—C13—C8	−1.7 (2)	C15—C16—C21—C20	−177.08 (16)
C11—C9—C13—C14	−1.0 (2)	C19—C20—C21—C16	−0.6 (3)