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

In the title compound, C(13)H(12)N(2)O(3), the dihedral angle between the aromatic rings is 7.94 (12)°. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(6) loops. Weak π-π [centroid-centroid separations = 3.7480 (13) and 3.9047 (13) Å] and C-H⋯π inter-actions help to consolidate the packing.

Related literature

For background to conjugated azo-methanes, see: Asiri & Khan (2010 ▶). For related structures, see: Asiri et al. (2010 ▶); Tahir et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H12N2O3

M = 244.25

Monoclinic,

a = 7.5759 (5) Å

b = 10.6980 (9) Å

c = 14.6307 (12) Å

β = 102.607 (2)°

V = 1157.19 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.980

8018 measured reflections

2087 independent reflections

1447 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.132

S = 1.03

2087 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 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/S1600536811030327/hb6330sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030327/hb6330Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030327/hb6330Isup3.cml

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

C13H12N2O3	F(000) = 512
Mr = 244.25	Dx = 1.402 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1447 reflections
a = 7.5759 (5) Å	θ = 3.4–25.3°
b = 10.6980 (9) Å	µ = 0.10 mm−1
c = 14.6307 (12) Å	T = 296 K
β = 102.607 (2)°	Prism, yellow
V = 1157.19 (16) Å3	0.28 × 0.24 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2087 independent reflections
Radiation source: fine-focus sealed tube	1447 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 3.4°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.975, Tmax = 0.980	l = −17→17
8018 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0693P)2 + 0.1704P] where P = (Fo2 + 2Fc2)/3
2087 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 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	0.6073 (2)	0.09898 (13)	0.08565 (10)	0.0729 (6)
O2	0.6345 (2)	0.27941 (14)	0.00426 (10)	0.0702 (6)
O3	0.6207 (2)	0.38037 (12)	0.55753 (10)	0.0699 (6)
N1	0.6338 (2)	0.23824 (15)	0.43533 (11)	0.0487 (5)
N2	0.6192 (3)	0.37712 (18)	0.65383 (13)	0.0742 (8)
C1	0.6183 (2)	0.31798 (17)	0.28025 (13)	0.0457 (6)
C2	0.6088 (3)	0.20099 (17)	0.23618 (13)	0.0493 (6)
C3	0.6150 (3)	0.19982 (17)	0.14411 (14)	0.0490 (7)
C4	0.6313 (3)	0.30805 (19)	0.09481 (13)	0.0510 (7)
C5	0.6386 (3)	0.42247 (19)	0.13520 (15)	0.0618 (8)
C6	0.6302 (3)	0.42546 (18)	0.22912 (14)	0.0572 (7)
C7	0.6271 (3)	0.1475 (2)	−0.00210 (15)	0.0687 (8)
C8	0.6190 (2)	0.33074 (18)	0.37881 (13)	0.0497 (7)
C9	0.6331 (3)	0.26031 (18)	0.52782 (13)	0.0478 (7)
C10	0.6405 (2)	0.18039 (18)	0.60027 (13)	0.0477 (7)
C11	0.6292 (3)	0.2593 (2)	0.67649 (14)	0.0556 (7)
C12	0.6270 (3)	0.2203 (2)	0.77363 (15)	0.0716 (9)
C13	0.6585 (3)	0.0425 (2)	0.60257 (15)	0.0697 (9)
H2	0.59873	0.12747	0.26857	0.0591*
H5	0.64865	0.49515	0.10183	0.0741*
H6	0.63264	0.50254	0.25877	0.0686*
H7A	0.73721	0.11561	−0.01717	0.0824*
H7B	0.52555	0.12203	−0.05118	0.0824*
H8	0.60811	0.41048	0.40229	0.0596*
H12A	0.51285	0.18213	0.77471	0.1074*
H12B	0.64420	0.29227	0.81383	0.1074*
H12C	0.72268	0.16145	0.79518	0.1074*
H13A	0.69485	0.01447	0.54709	0.1045*
H13B	0.54443	0.00536	0.60531	0.1045*
H13C	0.74801	0.01816	0.65679	0.1045*

	U11	U22	U33	U12	U13	U23
O1	0.1287 (13)	0.0486 (9)	0.0459 (9)	−0.0125 (8)	0.0292 (9)	−0.0072 (7)
O2	0.1149 (12)	0.0587 (10)	0.0411 (8)	−0.0105 (8)	0.0259 (8)	−0.0007 (7)
O3	0.1182 (12)	0.0479 (9)	0.0477 (9)	0.0126 (8)	0.0273 (8)	−0.0003 (7)
N1	0.0606 (10)	0.0462 (9)	0.0407 (9)	−0.0010 (7)	0.0143 (7)	0.0013 (7)
N2	0.1179 (16)	0.0650 (13)	0.0447 (11)	0.0151 (10)	0.0288 (10)	−0.0032 (9)
C1	0.0549 (11)	0.0427 (10)	0.0424 (10)	0.0009 (8)	0.0170 (8)	0.0031 (8)
C2	0.0648 (12)	0.0409 (10)	0.0445 (11)	−0.0023 (9)	0.0172 (9)	0.0050 (9)
C3	0.0631 (12)	0.0423 (11)	0.0432 (11)	−0.0035 (9)	0.0148 (9)	−0.0020 (9)
C4	0.0652 (12)	0.0526 (12)	0.0373 (10)	−0.0033 (9)	0.0157 (9)	0.0023 (9)
C5	0.0975 (16)	0.0443 (12)	0.0495 (12)	−0.0033 (10)	0.0291 (11)	0.0083 (9)
C6	0.0860 (15)	0.0407 (11)	0.0497 (12)	−0.0020 (10)	0.0253 (10)	−0.0009 (9)
C7	0.1030 (17)	0.0597 (14)	0.0456 (12)	−0.0082 (12)	0.0210 (11)	−0.0036 (10)
C8	0.0656 (13)	0.0431 (10)	0.0434 (11)	−0.0004 (9)	0.0186 (9)	−0.0022 (9)
C9	0.0591 (12)	0.0446 (11)	0.0410 (11)	0.0003 (8)	0.0140 (9)	−0.0023 (9)
C10	0.0517 (11)	0.0505 (12)	0.0404 (11)	−0.0020 (8)	0.0091 (8)	0.0009 (9)
C11	0.0582 (12)	0.0666 (14)	0.0426 (12)	0.0025 (10)	0.0122 (9)	0.0005 (10)
C12	0.0825 (16)	0.0934 (18)	0.0410 (12)	−0.0012 (13)	0.0179 (11)	0.0039 (12)
C13	0.0987 (17)	0.0543 (13)	0.0523 (14)	−0.0088 (11)	0.0083 (12)	0.0070 (10)

O1—C3	1.370 (2)	C9—C10	1.353 (3)
O1—C7	1.423 (3)	C10—C11	1.416 (3)
O2—C4	1.365 (2)	C10—C13	1.481 (3)
O2—C7	1.415 (3)	C11—C12	1.485 (3)
O3—N2	1.412 (2)	C2—H2	0.9300
O3—C9	1.366 (2)	C5—H5	0.9300
N1—C8	1.279 (2)	C6—H6	0.9300
N1—C9	1.375 (2)	C7—H7A	0.9700
N2—C11	1.301 (3)	C7—H7B	0.9700
C1—C2	1.403 (3)	C8—H8	0.9300
C1—C6	1.385 (3)	C12—H12A	0.9600
C1—C8	1.447 (3)	C12—H12B	0.9600
C2—C3	1.358 (3)	C12—H12C	0.9600
C3—C4	1.384 (3)	C13—H13A	0.9600
C4—C5	1.355 (3)	C13—H13B	0.9600
C5—C6	1.390 (3)	C13—H13C	0.9600
C3—O1—C7	106.12 (15)	C10—C11—C12	126.98 (19)
C4—O2—C7	106.20 (16)	C1—C2—H2	121.00
N2—O3—C9	108.09 (14)	C3—C2—H2	121.00
C8—N1—C9	119.01 (17)	C4—C5—H5	122.00
O3—N2—C11	105.39 (17)	C6—C5—H5	122.00
C2—C1—C6	119.69 (17)	C1—C6—H6	119.00
C2—C1—C8	122.06 (17)	C5—C6—H6	119.00
C6—C1—C8	118.24 (17)	O1—C7—H7A	110.00
C1—C2—C3	117.05 (17)	O1—C7—H7B	110.00
O1—C3—C2	128.35 (17)	O2—C7—H7A	110.00
O1—C3—C4	109.26 (17)	O2—C7—H7B	110.00
C2—C3—C4	122.39 (18)	H7A—C7—H7B	108.00
O2—C4—C3	109.91 (17)	N1—C8—H8	118.00
O2—C4—C5	128.19 (19)	C1—C8—H8	118.00
C3—C4—C5	121.89 (18)	C11—C12—H12A	109.00
C4—C5—C6	116.46 (19)	C11—C12—H12B	109.00
C1—C6—C5	122.49 (18)	C11—C12—H12C	109.00
O1—C7—O2	108.37 (16)	H12A—C12—H12B	109.00
N1—C8—C1	123.51 (17)	H12A—C12—H12C	110.00
O3—C9—N1	119.35 (16)	H12B—C12—H12C	109.00
O3—C9—C10	109.80 (16)	C10—C13—H13A	109.00
N1—C9—C10	130.84 (18)	C10—C13—H13B	110.00
C9—C10—C11	103.94 (17)	C10—C13—H13C	109.00
C9—C10—C13	129.41 (18)	H13A—C13—H13B	109.00
C11—C10—C13	126.65 (18)	H13A—C13—H13C	109.00
N2—C11—C10	112.77 (18)	H13B—C13—H13C	109.00
N2—C11—C12	120.26 (19)
C7—O1—C3—C2	−177.5 (2)	C6—C1—C8—N1	−170.00 (18)
C7—O1—C3—C4	2.4 (2)	C1—C2—C3—O1	−179.6 (2)
C3—O1—C7—O2	−3.8 (2)	C1—C2—C3—C4	0.5 (3)
C7—O2—C4—C3	−2.4 (2)	O1—C3—C4—O2	0.0 (3)
C7—O2—C4—C5	178.9 (2)	O1—C3—C4—C5	178.8 (2)
C4—O2—C7—O1	3.8 (2)	C2—C3—C4—O2	179.9 (2)
C9—O3—N2—C11	−0.4 (2)	C2—C3—C4—C5	−1.3 (4)
N2—O3—C9—N1	178.87 (19)	O2—C4—C5—C6	179.1 (2)
N2—O3—C9—C10	−0.3 (2)	C3—C4—C5—C6	0.5 (3)
C9—N1—C8—C1	179.97 (18)	C4—C5—C6—C1	1.1 (3)
C8—N1—C9—O3	−1.4 (3)	O3—C9—C10—C11	0.8 (2)
C8—N1—C9—C10	177.5 (2)	O3—C9—C10—C13	−178.49 (18)
O3—N2—C11—C10	0.9 (3)	N1—C9—C10—C11	−178.2 (2)
O3—N2—C11—C12	−178.74 (19)	N1—C9—C10—C13	2.5 (4)
C6—C1—C2—C3	1.1 (3)	C9—C10—C11—N2	−1.1 (3)
C8—C1—C2—C3	−177.91 (18)	C9—C10—C11—C12	178.5 (2)
C2—C1—C6—C5	−2.0 (3)	C13—C10—C11—N2	178.2 (2)
C8—C1—C6—C5	177.09 (19)	C13—C10—C11—C12	−2.2 (3)
C2—C1—C8—N1	9.0 (3)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1i	0.97	2.58	3.264 (3)	128
C12—H12A···Cg1ii	0.96	2.95	3.763 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O1i	0.97	2.58	3.264 (3)	128
C12—H12A⋯Cg1ii	0.96	2.95	3.763 (2)	143

Symmetry codes: (i) ; (ii) .