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

The mol-ecule of the title compound, C(12)H(11)ClN(2)O, has E configuration at the azomethine double bond and is virtually planar with a dihedral angle of 1.25 (13)° between the benzene and isoxazole rings. C-H⋯π inter-actions stabilize the crystal structure.

Related literature

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

Experimental

Crystal data

C12H11ClN2O

M = 234.68

Monoclinic,

a = 5.0877 (2) Å

b = 24.5197 (9) Å

c = 9.4673 (4) Å

β = 94.871 (2)°

V = 1176.77 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.30 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.868, T max = 0.965

9016 measured reflections

2112 independent reflections

1539 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 1.07

2112 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 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 text, I. DOI: 10.1107/S1600536810029284/gk2296sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029284/gk2296Isup2.hkl

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

C12H11ClN2O	F(000) = 488
Mr = 234.68	Dx = 1.325 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1539 reflections
a = 5.0877 (2) Å	θ = 2.3–25.3°
b = 24.5197 (9) Å	µ = 0.30 mm−1
c = 9.4673 (4) Å	T = 296 K
β = 94.871 (2)°	Needle, light brown
V = 1176.77 (8) Å3	0.30 × 0.16 × 0.14 mm
Z = 4

Bruker KAPPA APEXII CCD diffractometer	2112 independent reflections
Radiation source: fine-focus sealed tube	1539 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.3°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −29→29
Tmin = 0.868, Tmax = 0.965	l = −11→11
9016 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: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0521P)2 + 0.2476P] where P = (Fo2 + 2Fc2)/3
2112 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 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
Cl1	−0.59118 (13)	0.19483 (3)	−0.44471 (7)	0.0894 (3)
O1	0.5343 (3)	0.03641 (6)	0.15781 (16)	0.0736 (6)
N1	0.3653 (3)	0.11804 (7)	0.05045 (17)	0.0608 (6)
N2	0.7399 (4)	0.02071 (8)	0.2600 (2)	0.0763 (7)
C1	−0.0022 (4)	0.11701 (8)	−0.1255 (2)	0.0576 (7)
C2	−0.1918 (4)	0.08576 (9)	−0.2009 (2)	0.0676 (8)
C3	−0.3750 (4)	0.10921 (9)	−0.2987 (2)	0.0701 (8)
C4	−0.3674 (4)	0.16448 (9)	−0.3200 (2)	0.0630 (8)
C5	−0.1824 (5)	0.19639 (9)	−0.2446 (3)	0.0775 (9)
C6	−0.0019 (4)	0.17261 (10)	−0.1484 (3)	0.0724 (8)
C7	0.1915 (4)	0.09088 (9)	−0.0251 (2)	0.0622 (7)
C8	0.5459 (4)	0.09160 (9)	0.1431 (2)	0.0576 (7)
C9	0.7462 (4)	0.11227 (8)	0.2291 (2)	0.0575 (7)
C10	0.8603 (4)	0.06588 (9)	0.2988 (2)	0.0617 (7)
C11	1.0916 (4)	0.06456 (11)	0.4077 (2)	0.0785 (9)
C12	0.8318 (4)	0.16992 (9)	0.2438 (3)	0.0778 (9)
H2	−0.19609	0.04832	−0.18554	0.0811*
H3	−0.50149	0.08784	−0.34921	0.0842*
H5	−0.18016	0.23391	−0.25895	0.0930*
H6	0.12298	0.19425	−0.09757	0.0869*
H7	0.18824	0.05313	−0.01578	0.0746*
H11A	1.15318	0.02772	0.42002	0.1177*
H11B	1.03940	0.07821	0.49613	0.1177*
H11C	1.23056	0.08692	0.37665	0.1177*
H12A	0.72003	0.19230	0.18085	0.1168*
H12B	1.01097	0.17312	0.22023	0.1168*
H12C	0.81971	0.18168	0.33972	0.1168*

	U11	U22	U33	U12	U13	U23
Cl1	0.0947 (5)	0.0856 (5)	0.0842 (4)	0.0155 (3)	−0.0142 (3)	0.0044 (3)
O1	0.0787 (10)	0.0567 (9)	0.0821 (10)	−0.0045 (7)	−0.0123 (8)	−0.0012 (7)
N1	0.0579 (10)	0.0613 (11)	0.0634 (10)	−0.0002 (8)	0.0067 (8)	−0.0017 (8)
N2	0.0797 (12)	0.0638 (12)	0.0816 (12)	0.0000 (10)	−0.0161 (10)	0.0055 (10)
C1	0.0568 (11)	0.0568 (12)	0.0597 (11)	0.0007 (9)	0.0079 (9)	−0.0057 (9)
C2	0.0741 (14)	0.0517 (12)	0.0761 (14)	−0.0019 (10)	0.0014 (11)	−0.0053 (11)
C3	0.0702 (14)	0.0664 (14)	0.0715 (14)	−0.0028 (11)	−0.0071 (11)	−0.0110 (11)
C4	0.0642 (13)	0.0644 (14)	0.0602 (12)	0.0080 (10)	0.0041 (10)	−0.0028 (10)
C5	0.0836 (16)	0.0537 (13)	0.0932 (17)	−0.0027 (11)	−0.0041 (13)	0.0021 (12)
C6	0.0709 (14)	0.0617 (14)	0.0822 (15)	−0.0064 (11)	−0.0074 (11)	−0.0056 (12)
C7	0.0663 (13)	0.0559 (12)	0.0647 (12)	0.0006 (10)	0.0077 (10)	−0.0048 (10)
C8	0.0589 (12)	0.0548 (12)	0.0598 (11)	0.0013 (9)	0.0099 (9)	−0.0006 (9)
C9	0.0565 (11)	0.0618 (13)	0.0552 (11)	−0.0041 (10)	0.0102 (9)	−0.0011 (10)
C10	0.0633 (12)	0.0647 (13)	0.0575 (11)	−0.0039 (11)	0.0082 (9)	0.0004 (10)
C11	0.0716 (14)	0.0913 (18)	0.0708 (14)	−0.0056 (12)	−0.0044 (11)	0.0059 (12)
C12	0.0793 (15)	0.0613 (14)	0.0921 (16)	−0.0106 (12)	0.0026 (12)	−0.0055 (12)

Cl1—C4	1.737 (2)	C9—C10	1.415 (3)
O1—N2	1.417 (2)	C9—C12	1.482 (3)
O1—C8	1.362 (3)	C10—C11	1.498 (3)
N1—C7	1.277 (3)	C2—H2	0.9300
N1—C8	1.377 (3)	C3—H3	0.9300
N2—C10	1.303 (3)	C5—H5	0.9300
C1—C2	1.382 (3)	C6—H6	0.9300
C1—C6	1.380 (3)	C7—H7	0.9300
C1—C7	1.458 (3)	C11—H11A	0.9600
C2—C3	1.382 (3)	C11—H11B	0.9600
C3—C4	1.371 (3)	C11—H11C	0.9600
C4—C5	1.376 (3)	C12—H12A	0.9600
C5—C6	1.368 (4)	C12—H12B	0.9600
C8—C9	1.348 (3)	C12—H12C	0.9600
Cl1···H12Ci	3.0600	C12···H11C	3.0700
O1···H7	2.3400	H2···H7	2.4300
O1···H2ii	2.7200	H2···O1ii	2.7200
N1···H6	2.5800	H3···C11vi	3.0200
N1···H12A	2.7800	H6···N1	2.5800
N1···H12Biii	2.8500	H7···O1	2.3400
C3···C7iii	3.570 (3)	H7···H2	2.4300
C7···C3iv	3.570 (3)	H11B···C3vii	3.0800
C7···C9iii	3.482 (3)	H11C···C8iv	2.8400
C9···C7iv	3.482 (3)	H11C···C12	3.0700
C3···H11Bi	3.0800	H12A···N1	2.7800
C8···H11Ciii	2.8400	H12B···N1iv	2.8500
C11···H3v	3.0200	H12C···Cl1vii	3.0600
N2—O1—C8	107.69 (15)	C1—C2—H2	119.00
C7—N1—C8	120.28 (18)	C3—C2—H2	119.00
O1—N2—C10	105.29 (17)	C2—C3—H3	121.00
C2—C1—C6	118.45 (19)	C4—C3—H3	121.00
C2—C1—C7	119.77 (18)	C4—C5—H5	120.00
C6—C1—C7	121.78 (19)	C6—C5—H5	120.00
C1—C2—C3	121.1 (2)	C1—C6—H6	119.00
C2—C3—C4	118.94 (19)	C5—C6—H6	119.00
Cl1—C4—C3	119.90 (16)	N1—C7—H7	119.00
Cl1—C4—C5	119.28 (18)	C1—C7—H7	119.00
C3—C4—C5	120.82 (19)	C10—C11—H11A	109.00
C4—C5—C6	119.6 (2)	C10—C11—H11B	109.00
C1—C6—C5	121.1 (2)	C10—C11—H11C	109.00
N1—C7—C1	122.3 (2)	H11A—C11—H11B	109.00
O1—C8—N1	120.02 (18)	H11A—C11—H11C	109.00
O1—C8—C9	110.42 (18)	H11B—C11—H11C	109.00
N1—C8—C9	129.6 (2)	C9—C12—H12A	109.00
C8—C9—C10	103.81 (18)	C9—C12—H12B	109.00
C8—C9—C12	128.04 (19)	C9—C12—H12C	109.00
C10—C9—C12	128.13 (19)	H12A—C12—H12B	109.00
N2—C10—C9	112.79 (18)	H12A—C12—H12C	109.00
N2—C10—C11	119.9 (2)	H12B—C12—H12C	110.00
C9—C10—C11	127.3 (2)
C8—O1—N2—C10	−0.4 (2)	C1—C2—C3—C4	−0.3 (3)
N2—O1—C8—N1	−179.39 (17)	C2—C3—C4—Cl1	178.75 (15)
N2—O1—C8—C9	0.1 (2)	C2—C3—C4—C5	−0.6 (3)
C8—N1—C7—C1	−179.45 (18)	Cl1—C4—C5—C6	−178.59 (19)
C7—N1—C8—O1	−2.1 (3)	C3—C4—C5—C6	0.8 (4)
C7—N1—C8—C9	178.5 (2)	C4—C5—C6—C1	0.0 (4)
O1—N2—C10—C9	0.5 (2)	O1—C8—C9—C10	0.2 (2)
O1—N2—C10—C11	179.91 (17)	O1—C8—C9—C12	178.5 (2)
C6—C1—C2—C3	1.0 (3)	N1—C8—C9—C10	179.6 (2)
C7—C1—C2—C3	−178.80 (18)	N1—C8—C9—C12	−2.1 (4)
C2—C1—C6—C5	−0.8 (3)	C8—C9—C10—N2	−0.4 (2)
C7—C1—C6—C5	179.0 (2)	C8—C9—C10—C11	−179.78 (19)
C2—C1—C7—N1	−177.71 (19)	C12—C9—C10—N2	−178.7 (2)
C6—C1—C7—N1	2.5 (3)	C12—C9—C10—C11	1.9 (3)

Cg1 is the centroid of the O1/N2/C10/C9/C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.93	2.34	2.704 (3)	103
C11—H11C···Cg1iv	0.96	2.91	3.644 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the O1/N2/C10/C9/C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11C⋯Cg1i	0.96	2.91	3.644 (2)	134

Symmetry code: (i) .