N-[(E)-Anthracen-9-yl-methyl-idene]-3,4-dimethyl-1,2-oxazol-5-amine.

In the title compound, C(20)H(16)N(2)O, an intra-molecular C-H⋯N forms an S(6) ring motif. In the crystal, the mol-ecules are stacked with their anthracene ring planes in sheets along [100].

Related literature

For applications of compounds containing azomethine groups, see: Khuhawar et al. (2004 ▶). Schiff base compounds demonstrate anti­bacterial (Asiri & Khan, 2010 ▶), anti­tumor activity (Saxena & Tandon, 1983 ▶) and anti-HIV activity (Pandeya et al., 1999 ▶). For related structures, see: Asiri et al. (2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H16N2O

M = 300.35

Monoclinic,

a = 22.4919 (14) Å

b = 6.1666 (4) Å

c = 22.6801 (13) Å

β = 102.015 (2)°

V = 3076.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.975, T max = 0.980

12925 measured reflections

3193 independent reflections

2381 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.04

3193 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050471/fk2045sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050471/fk2045Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050471/fk2045Isup3.cml

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

C20H16N2O	F(000) = 1264
Mr = 300.35	Dx = 1.297 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2381 reflections
a = 22.4919 (14) Å	θ = 1.9–26.5°
b = 6.1666 (4) Å	µ = 0.08 mm−1
c = 22.6801 (13) Å	T = 296 K
β = 102.015 (2)°	Prism, red
V = 3076.8 (3) Å3	0.32 × 0.24 × 0.22 mm
Z = 8

Bruker KAPPA APEXII CCD diffractometer	3193 independent reflections
Radiation source: fine-focus sealed tube	2381 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 8.10 pixels mm-1	θmax = 26.5°, θmin = 1.9°
ω scans	h = −28→27
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −7→7
Tmin = 0.975, Tmax = 0.980	l = −23→28
12925 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)] = 0.044	Hydrogen site location: geom and difmap
wR(F2) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0637P)2 + 1.2672P] where P = (Fo2 + 2Fc2)/3
3193 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.09676 (5)	0.50025 (19)	0.05196 (5)	0.0516 (4)
N1	0.10276 (6)	0.2014 (2)	0.11940 (6)	0.0459 (4)
N2	0.05953 (7)	0.6861 (3)	0.03694 (7)	0.0584 (5)
C1	0.16650 (6)	−0.1894 (3)	0.17670 (6)	0.0379 (4)
C2	0.12182 (7)	−0.1253 (3)	0.20964 (7)	0.0486 (5)
C3	0.10875 (8)	−0.2518 (3)	0.25450 (8)	0.0580 (6)
C4	0.13754 (8)	−0.4522 (3)	0.26932 (8)	0.0606 (7)
C5	0.17975 (8)	−0.5201 (3)	0.23969 (8)	0.0528 (6)
C6	0.19672 (7)	−0.3919 (3)	0.19346 (7)	0.0403 (5)
C7	0.24311 (7)	−0.4589 (3)	0.16590 (7)	0.0429 (5)
C8	0.26386 (7)	−0.3322 (3)	0.12393 (6)	0.0393 (5)
C9	0.31446 (7)	−0.3980 (3)	0.09933 (7)	0.0497 (6)
C10	0.33622 (8)	−0.2712 (3)	0.06009 (8)	0.0556 (6)
C11	0.30869 (8)	−0.0702 (3)	0.04332 (8)	0.0554 (6)
C12	0.25992 (7)	−0.0016 (3)	0.06472 (7)	0.0476 (5)
C13	0.23446 (6)	−0.1286 (2)	0.10601 (6)	0.0365 (5)
C14	0.18386 (6)	−0.0631 (2)	0.13028 (6)	0.0356 (4)
C15	0.15128 (7)	0.1314 (2)	0.10573 (7)	0.0398 (5)
C16	0.07545 (7)	0.3889 (3)	0.09501 (7)	0.0415 (5)
C17	0.02670 (7)	0.4911 (3)	0.10808 (7)	0.0447 (5)
C18	0.01918 (7)	0.6751 (3)	0.07070 (8)	0.0501 (6)
C19	−0.02801 (9)	0.8473 (3)	0.06716 (10)	0.0733 (8)
C20	−0.00958 (9)	0.4243 (4)	0.15280 (9)	0.0675 (7)
H2	0.10126	0.00518	0.20030	0.0584*
H3	0.08009	−0.20426	0.27582	0.0696*
H4	0.12735	−0.53754	0.29956	0.0728*
H5	0.19841	−0.65363	0.24946	0.0633*
H7	0.26093	−0.59368	0.17593	0.0515*
H9	0.33285	−0.53105	0.11056	0.0596*
H10	0.36913	−0.31682	0.04434	0.0667*
H11	0.32424	0.01809	0.01692	0.0666*
H12	0.24256	0.13187	0.05217	0.0571*
H15	0.16724	0.21079	0.07779	0.0478*
H19A	−0.02371	0.91685	0.10569	0.1099*
H19B	−0.06768	0.78325	0.05612	0.1099*
H19C	−0.02301	0.95261	0.03740	0.1099*
H20A	0.00725	0.29388	0.17266	0.1013*
H20B	−0.05088	0.39842	0.13254	0.1013*
H20C	−0.00855	0.53733	0.18209	0.1013*

	U11	U22	U33	U12	U13	U23
O1	0.0536 (7)	0.0504 (7)	0.0565 (7)	0.0142 (5)	0.0243 (5)	0.0109 (5)
N1	0.0428 (7)	0.0438 (8)	0.0535 (8)	0.0056 (6)	0.0158 (6)	0.0045 (6)
N2	0.0621 (9)	0.0510 (9)	0.0640 (10)	0.0189 (7)	0.0177 (8)	0.0137 (7)
C1	0.0335 (7)	0.0412 (8)	0.0383 (8)	−0.0033 (6)	0.0061 (6)	−0.0001 (6)
C2	0.0451 (9)	0.0550 (10)	0.0495 (9)	0.0033 (8)	0.0184 (7)	0.0062 (8)
C3	0.0509 (10)	0.0745 (13)	0.0539 (10)	−0.0015 (9)	0.0232 (8)	0.0084 (9)
C4	0.0559 (11)	0.0746 (13)	0.0533 (10)	−0.0048 (10)	0.0157 (8)	0.0243 (10)
C5	0.0492 (10)	0.0527 (10)	0.0539 (10)	−0.0015 (8)	0.0051 (8)	0.0167 (8)
C6	0.0380 (8)	0.0401 (9)	0.0403 (8)	−0.0045 (7)	0.0022 (6)	0.0036 (7)
C7	0.0411 (8)	0.0374 (8)	0.0472 (9)	0.0045 (7)	0.0021 (7)	0.0024 (7)
C8	0.0360 (8)	0.0410 (9)	0.0394 (8)	0.0027 (6)	0.0043 (6)	−0.0051 (7)
C9	0.0426 (9)	0.0536 (10)	0.0522 (10)	0.0125 (8)	0.0085 (7)	−0.0051 (8)
C10	0.0421 (9)	0.0734 (13)	0.0548 (10)	0.0113 (9)	0.0180 (8)	−0.0067 (9)
C11	0.0489 (10)	0.0699 (12)	0.0530 (10)	0.0021 (9)	0.0232 (8)	0.0059 (9)
C12	0.0455 (9)	0.0513 (10)	0.0489 (9)	0.0067 (8)	0.0168 (7)	0.0078 (8)
C13	0.0341 (8)	0.0395 (9)	0.0356 (7)	0.0008 (6)	0.0064 (6)	−0.0028 (6)
C14	0.0329 (7)	0.0372 (8)	0.0368 (7)	0.0000 (6)	0.0076 (6)	−0.0010 (6)
C15	0.0392 (8)	0.0405 (9)	0.0429 (8)	0.0026 (7)	0.0157 (6)	0.0023 (7)
C16	0.0407 (8)	0.0419 (9)	0.0437 (8)	0.0021 (7)	0.0132 (7)	0.0006 (7)
C17	0.0396 (8)	0.0453 (9)	0.0507 (9)	0.0041 (7)	0.0127 (7)	−0.0054 (7)
C18	0.0442 (9)	0.0495 (10)	0.0553 (10)	0.0090 (8)	0.0077 (8)	−0.0045 (8)
C19	0.0640 (13)	0.0621 (13)	0.0937 (16)	0.0253 (10)	0.0162 (11)	−0.0007 (11)
C20	0.0554 (11)	0.0771 (14)	0.0791 (13)	0.0055 (10)	0.0347 (10)	−0.0032 (11)

O1—N2	1.418 (2)	C14—C15	1.4545 (19)
O1—C16	1.360 (2)	C16—C17	1.350 (2)
N1—C15	1.271 (2)	C17—C18	1.405 (3)
N1—C16	1.371 (2)	C17—C20	1.486 (3)
N2—C18	1.305 (2)	C18—C19	1.492 (3)
C1—C2	1.427 (2)	C2—H2	0.9300
C1—C6	1.435 (3)	C3—H3	0.9300
C1—C14	1.428 (2)	C4—H4	0.9300
C2—C3	1.362 (2)	C5—H5	0.9300
C3—C4	1.403 (3)	C7—H7	0.9300
C4—C5	1.339 (3)	C9—H9	0.9300
C5—C6	1.427 (2)	C10—H10	0.9300
C6—C7	1.386 (2)	C11—H11	0.9300
C7—C8	1.385 (2)	C12—H12	0.9300
C8—C9	1.427 (2)	C15—H15	0.9300
C8—C13	1.438 (2)	C19—H19A	0.9600
C9—C10	1.351 (2)	C19—H19B	0.9600
C10—C11	1.402 (3)	C19—H19C	0.9600
C11—C12	1.356 (2)	C20—H20A	0.9600
C12—C13	1.429 (2)	C20—H20B	0.9600
C13—C14	1.4220 (19)	C20—H20C	0.9600
N2—O1—C16	107.56 (12)	N2—C18—C19	120.35 (17)
C15—N1—C16	121.58 (14)	C17—C18—C19	127.02 (16)
O1—N2—C18	105.36 (15)	C1—C2—H2	119.00
C2—C1—C6	116.67 (14)	C3—C2—H2	119.00
C2—C1—C14	124.43 (15)	C2—C3—H3	119.00
C6—C1—C14	118.88 (13)	C4—C3—H3	119.00
C1—C2—C3	121.16 (16)	C3—C4—H4	120.00
C2—C3—C4	121.52 (17)	C5—C4—H4	120.00
C3—C4—C5	119.68 (17)	C4—C5—H5	119.00
C4—C5—C6	121.43 (17)	C6—C5—H5	119.00
C1—C6—C5	119.50 (15)	C6—C7—H7	119.00
C1—C6—C7	119.97 (15)	C8—C7—H7	119.00
C5—C6—C7	120.51 (16)	C8—C9—H9	119.00
C6—C7—C8	122.32 (17)	C10—C9—H9	119.00
C7—C8—C9	121.24 (16)	C9—C10—H10	120.00
C7—C8—C13	119.07 (14)	C11—C10—H10	120.00
C9—C8—C13	119.68 (14)	C10—C11—H11	119.00
C8—C9—C10	121.40 (17)	C12—C11—H11	119.00
C9—C10—C11	119.36 (17)	C11—C12—H12	119.00
C10—C11—C12	121.53 (17)	C13—C12—H12	119.00
C11—C12—C13	121.87 (16)	N1—C15—H15	117.00
C8—C13—C12	116.13 (13)	C14—C15—H15	117.00
C8—C13—C14	119.78 (12)	C18—C19—H19A	109.00
C12—C13—C14	124.07 (12)	C18—C19—H19B	109.00
C1—C14—C13	119.62 (12)	C18—C19—H19C	109.00
C1—C14—C15	122.60 (13)	H19A—C19—H19B	109.00
C13—C14—C15	117.78 (12)	H19A—C19—H19C	109.00
N1—C15—C14	125.21 (14)	H19B—C19—H19C	109.00
O1—C16—N1	121.36 (14)	C17—C20—H20A	109.00
O1—C16—C17	110.22 (15)	C17—C20—H20B	109.00
N1—C16—C17	128.42 (15)	C17—C20—H20C	109.00
C16—C17—C18	104.22 (14)	H20A—C20—H20B	109.00
C16—C17—C20	127.36 (17)	H20A—C20—H20C	109.00
C18—C17—C20	128.41 (17)	H20B—C20—H20C	109.00
N2—C18—C17	112.63 (16)
C16—O1—N2—C18	−0.22 (18)	C6—C7—C8—C13	−3.1 (2)
N2—O1—C16—N1	−179.18 (14)	C7—C8—C9—C10	−177.53 (16)
N2—O1—C16—C17	0.46 (18)	C13—C8—C9—C10	1.1 (2)
C16—N1—C15—C14	178.72 (14)	C7—C8—C13—C12	177.20 (14)
C15—N1—C16—O1	4.6 (2)	C7—C8—C13—C14	−1.6 (2)
C15—N1—C16—C17	−174.96 (17)	C9—C8—C13—C12	−1.5 (2)
O1—N2—C18—C17	−0.09 (19)	C9—C8—C13—C14	179.74 (14)
O1—N2—C18—C19	179.65 (15)	C8—C9—C10—C11	0.3 (3)
C6—C1—C2—C3	−0.2 (2)	C9—C10—C11—C12	−1.3 (3)
C14—C1—C2—C3	−178.22 (15)	C10—C11—C12—C13	0.8 (3)
C2—C1—C6—C5	2.0 (2)	C11—C12—C13—C8	0.5 (2)
C2—C1—C6—C7	−176.27 (15)	C11—C12—C13—C14	179.27 (15)
C14—C1—C6—C5	−179.86 (15)	C8—C13—C14—C1	6.3 (2)
C14—C1—C6—C7	1.8 (2)	C8—C13—C14—C15	−173.06 (13)
C2—C1—C14—C13	171.60 (14)	C12—C13—C14—C1	−172.43 (14)
C2—C1—C14—C15	−9.1 (2)	C12—C13—C14—C15	8.3 (2)
C6—C1—C14—C13	−6.3 (2)	C1—C14—C15—N1	−4.8 (2)
C6—C1—C14—C15	172.94 (14)	C13—C14—C15—N1	174.48 (14)
C1—C2—C3—C4	−1.5 (3)	O1—C16—C17—C18	−0.49 (19)
C2—C3—C4—C5	1.3 (3)	O1—C16—C17—C20	−179.47 (17)
C3—C4—C5—C6	0.6 (3)	N1—C16—C17—C18	179.11 (17)
C4—C5—C6—C1	−2.3 (3)	N1—C16—C17—C20	0.1 (3)
C4—C5—C6—C7	176.03 (17)	C16—C17—C18—N2	0.4 (2)
C1—C6—C7—C8	3.0 (2)	C16—C17—C18—C19	−179.36 (18)
C5—C6—C7—C8	−175.34 (16)	C20—C17—C18—N2	179.32 (18)
C6—C7—C8—C9	175.57 (15)	C20—C17—C18—C19	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1	0.93	2.20	2.840 (2)	125
C15—H15···O1	0.93	2.38	2.7463 (18)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1	0.93	2.20	2.840 (2)	125