N-(4-Bromo-benzyl-idene)-3,4-dimethyl-isoxazol-5-amine.

In the title compound, C(12)H(11)BrN(2)O, the 4-bromo-benzaldehyde and 5-amino-3,4-dimethyl-isoxazole units are oriented at a dihedral angle of 4.89 (8)°. In the crystal, weak π-π inter-actions are present between the benzene rings at a centroid-centroid distance of 3.7862 (14) Å.

Related literature

For related structures, see: Asiri et al. (2010 ▶): Fun et al. (2010a ▶,b ▶): Shad et al. (2008 ▶): Tahir et al. (2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H11BrN2O

M = 279.14

Triclinic,

a = 7.6406 (4) Å

b = 8.8709 (5) Å

c = 9.1052 (5) Å

α = 97.024 (2)°

β = 102.961 (1)°

γ = 92.786 (2)°

V = 595.06 (6) Å3

Z = 2

Mo Kα radiation

μ = 3.43 mm−1

T = 296 K

0.30 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.568, T max = 0.665

8212 measured reflections

2119 independent reflections

1643 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.059

S = 1.03

2119 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 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 datablocks global, I. DOI: 10.1107/S1600536810027893/bq2226sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027893/bq2226Isup2.hkl

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

C12H11BrN2O	Z = 2
Mr = 279.14	F(000) = 280
Triclinic, P1	Dx = 1.558 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6406 (4) Å	Cell parameters from 1643 reflections
b = 8.8709 (5) Å	θ = 2.3–25.3°
c = 9.1052 (5) Å	µ = 3.43 mm−1
α = 97.024 (2)°	T = 296 K
β = 102.961 (1)°	Needle, brown
γ = 92.786 (2)°	0.30 × 0.14 × 0.12 mm
V = 595.06 (6) Å3

Bruker Kappa APEXII CCD diffractometer	2119 independent reflections
Radiation source: fine-focus sealed tube	1643 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.3°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.568, Tmax = 0.665	l = −10→10
8212 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0225P)2 + 0.2246P] where P = (Fo2 + 2Fc2)/3
2119 reflections	(Δ/σ)max = 0.001
147 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.17 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
Br1	−0.32255 (4)	1.00984 (3)	0.72075 (3)	0.0712 (1)
O1	0.4539 (2)	0.51578 (18)	0.30328 (18)	0.0572 (6)
N1	0.1487 (3)	0.55019 (19)	0.3071 (2)	0.0440 (6)
N2	0.5503 (3)	0.4289 (3)	0.2111 (3)	0.0656 (8)
C1	0.0706 (3)	0.7262 (2)	0.4987 (2)	0.0421 (8)
C2	−0.1140 (3)	0.7008 (2)	0.4413 (3)	0.0471 (8)
C3	−0.2317 (3)	0.7844 (3)	0.5070 (3)	0.0509 (8)
C4	−0.1622 (3)	0.8940 (2)	0.6301 (3)	0.0489 (9)
C5	0.0186 (4)	0.9215 (3)	0.6888 (3)	0.0571 (9)
C6	0.1356 (3)	0.8365 (3)	0.6240 (3)	0.0538 (9)
C7	0.1988 (3)	0.6429 (2)	0.4298 (3)	0.0455 (8)
C8	0.2749 (3)	0.4794 (2)	0.2430 (3)	0.0433 (8)
C9	0.2501 (3)	0.3744 (2)	0.1180 (3)	0.0457 (8)
C10	0.4265 (3)	0.3478 (3)	0.1044 (3)	0.0517 (9)
C11	0.4836 (4)	0.2423 (3)	−0.0149 (3)	0.0745 (11)
C12	0.0764 (4)	0.3028 (3)	0.0200 (3)	0.0659 (10)
H2	−0.15915	0.62688	0.35786	0.0565*
H3	−0.35551	0.76687	0.46887	0.0611*
H5	0.06270	0.99657	0.77139	0.0686*
H6	0.25905	0.85335	0.66457	0.0646*
H7	0.32075	0.65805	0.47691	0.0546*
H11A	0.61269	0.24881	0.00435	0.1118*
H11B	0.43483	0.27080	−0.11341	0.1118*
H11C	0.43975	0.13964	−0.01207	0.1118*
H12A	−0.02153	0.34332	0.05809	0.0989*
H12B	0.07209	0.19462	0.02086	0.0989*
H12C	0.06658	0.32433	−0.08221	0.0989*

	U11	U22	U33	U12	U13	U23
Br1	0.0760 (2)	0.0641 (2)	0.0851 (2)	0.0188 (1)	0.0448 (2)	0.0012 (1)
O1	0.0487 (11)	0.0650 (10)	0.0542 (10)	0.0090 (8)	0.0134 (8)	−0.0109 (8)
N1	0.0499 (12)	0.0408 (10)	0.0421 (11)	0.0068 (8)	0.0138 (9)	0.0023 (9)
N2	0.0549 (14)	0.0742 (14)	0.0684 (15)	0.0155 (11)	0.0226 (12)	−0.0074 (12)
C1	0.0501 (15)	0.0399 (12)	0.0394 (13)	0.0059 (10)	0.0163 (10)	0.0061 (10)
C2	0.0523 (16)	0.0422 (12)	0.0466 (14)	0.0001 (10)	0.0157 (11)	−0.0006 (10)
C3	0.0448 (15)	0.0493 (13)	0.0603 (16)	0.0033 (10)	0.0164 (12)	0.0063 (12)
C4	0.0598 (17)	0.0419 (12)	0.0521 (15)	0.0077 (10)	0.0271 (12)	0.0063 (11)
C5	0.0624 (19)	0.0568 (15)	0.0492 (15)	0.0015 (12)	0.0174 (12)	−0.0115 (12)
C6	0.0456 (15)	0.0632 (15)	0.0486 (15)	0.0020 (11)	0.0104 (11)	−0.0063 (12)
C7	0.0449 (14)	0.0482 (13)	0.0446 (14)	0.0075 (10)	0.0117 (10)	0.0071 (11)
C8	0.0476 (15)	0.0428 (12)	0.0410 (13)	0.0081 (10)	0.0119 (10)	0.0065 (10)
C9	0.0590 (16)	0.0397 (12)	0.0398 (13)	0.0087 (10)	0.0140 (11)	0.0045 (10)
C10	0.0652 (17)	0.0456 (13)	0.0482 (15)	0.0143 (12)	0.0209 (13)	0.0037 (11)
C11	0.089 (2)	0.0725 (18)	0.0698 (19)	0.0249 (15)	0.0379 (16)	−0.0036 (14)
C12	0.073 (2)	0.0616 (16)	0.0553 (16)	0.0060 (13)	0.0070 (14)	−0.0075 (13)

Br1—C4	1.899 (2)	C9—C10	1.409 (3)
O1—N2	1.420 (3)	C9—C12	1.486 (4)
O1—C8	1.361 (3)	C10—C11	1.500 (4)
N1—C7	1.274 (3)	C2—H2	0.9300
N1—C8	1.374 (3)	C3—H3	0.9300
N2—C10	1.307 (4)	C5—H5	0.9300
C1—C2	1.387 (3)	C6—H6	0.9300
C1—C6	1.390 (3)	C7—H7	0.9300
C1—C7	1.460 (3)	C11—H11A	0.9600
C2—C3	1.384 (3)	C11—H11B	0.9600
C3—C4	1.378 (4)	C11—H11C	0.9600
C4—C5	1.363 (4)	C12—H12A	0.9600
C5—C6	1.382 (4)	C12—H12B	0.9600
C8—C9	1.351 (3)	C12—H12C	0.9600
Br1···C11i	3.595 (3)	C4···C6ii	3.553 (3)
Br1···C7ii	3.687 (2)	C6···C4ii	3.553 (3)
O1···C3iii	3.355 (3)	C7···Br1ii	3.687 (2)
O1···H3iii	2.6900	C7···C2iv	3.481 (3)
O1···H7	2.3400	C8···C3iv	3.512 (3)
N1···C2iv	3.426 (3)	C11···Br1viii	3.595 (3)
N1···H2	2.6000	H2···N1	2.6000
N1···H12A	2.7600	H2···N2vii	2.7400
N1···H12Cv	2.7100	H3···O1vii	2.6900
N2···H2iii	2.7400	H6···H7	2.4200
N2···H11Bvi	2.9100	H7···O1	2.3400
C2···N1iv	3.426 (3)	H7···H6	2.4200
C2···C7iv	3.481 (3)	H11B···N2vi	2.9100
C3···O1vii	3.355 (3)	H12A···N1	2.7600
C3···C8iv	3.512 (3)	H12C···N1v	2.7100
N2—O1—C8	107.76 (18)	C1—C2—H2	120.00
C7—N1—C8	119.9 (2)	C3—C2—H2	120.00
O1—N2—C10	105.0 (2)	C2—C3—H3	121.00
C2—C1—C6	118.9 (2)	C4—C3—H3	121.00
C2—C1—C7	122.08 (18)	C4—C5—H5	120.00
C6—C1—C7	119.0 (2)	C6—C5—H5	120.00
C1—C2—C3	120.6 (2)	C1—C6—H6	120.00
C2—C3—C4	118.8 (2)	C5—C6—H6	120.00
Br1—C4—C3	119.17 (18)	N1—C7—H7	119.00
Br1—C4—C5	119.02 (19)	C1—C7—H7	119.00
C3—C4—C5	121.8 (2)	C10—C11—H11A	109.00
C4—C5—C6	119.2 (2)	C10—C11—H11B	109.00
C1—C6—C5	120.6 (2)	C10—C11—H11C	109.00
N1—C7—C1	122.0 (2)	H11A—C11—H11B	109.00
O1—C8—N1	120.5 (2)	H11A—C11—H11C	109.00
O1—C8—C9	110.4 (2)	H11B—C11—H11C	109.00
N1—C8—C9	129.2 (2)	C9—C12—H12A	109.00
C8—C9—C10	103.9 (2)	C9—C12—H12B	109.00
C8—C9—C12	127.6 (2)	C9—C12—H12C	109.00
C10—C9—C12	128.5 (2)	H12A—C12—H12B	110.00
N2—C10—C9	113.0 (2)	H12A—C12—H12C	109.00
N2—C10—C11	118.9 (2)	H12B—C12—H12C	109.00
C9—C10—C11	128.1 (2)
C8—O1—N2—C10	−0.1 (3)	C1—C2—C3—C4	0.3 (4)
N2—O1—C8—C9	0.1 (2)	C2—C3—C4—Br1	179.81 (18)
N2—O1—C8—N1	−178.1 (2)	C2—C3—C4—C5	−0.3 (4)
C7—N1—C8—C9	177.3 (2)	Br1—C4—C5—C6	179.42 (19)
C8—N1—C7—C1	177.18 (18)	C3—C4—C5—C6	−0.5 (4)
C7—N1—C8—O1	−4.8 (3)	C4—C5—C6—C1	1.2 (4)
O1—N2—C10—C9	0.1 (3)	O1—C8—C9—C10	0.0 (3)
O1—N2—C10—C11	179.6 (2)	N1—C8—C9—C12	−2.8 (4)
C2—C1—C6—C5	−1.2 (3)	O1—C8—C9—C12	179.1 (2)
C6—C1—C2—C3	0.4 (3)	N1—C8—C9—C10	178.0 (2)
C7—C1—C2—C3	−178.4 (2)	C8—C9—C10—N2	−0.1 (3)
C7—C1—C6—C5	177.6 (2)	C12—C9—C10—C11	1.4 (4)
C2—C1—C7—N1	5.0 (3)	C8—C9—C10—C11	−179.5 (3)
C6—C1—C7—N1	−173.7 (2)	C12—C9—C10—N2	−179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.9300	2.3400	2.702 (3)	103.00