1-(But-2-enyl-idene)-2-(2-nitro-phen-yl)hydrazine.

The mol-ecule of the title Schiff base compound, C(10)H(11)N(3)O(2), adopts an E geometry with respect to the C=N double bond. The mol-ecule is roughly planar, with the largest deviation from the mean plane being 0.111 (2) Å, The enyl-idene-hydrazine group is, however, slightly twisted with respect to the phenyl ring, making a dihedral angle of 6.5 (3)°. An intra-molecular N-H⋯O hydrogen bond may be responsible for the planar conformation. An inter-molecular N-H⋯O hydrogen bond links two mol-ecules around an inversion center, building a pseudo dimer.

Related literature

For the role played by Schiff base compounds in the development of various proteins and enzymes, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶).

Experimental

Crystal data

C10H11N3O2

M = 205.22

Triclinic,

a = 4.2390 (6) Å

b = 11.456 (2) Å

c = 11.9840 (17) Å

α = 113.271 (15)°

β = 96.534 (12)°

γ = 95.595 (13)°

V = 524.64 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.25 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.979, T max = 0.982

3321 measured reflections

1758 independent reflections

587 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.080

S = 0.68

1758 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037179/dn2487sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037179/dn2487Isup2.hkl

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

C10H11N3O2	Z = 2
Mr = 205.22	F(000) = 216
Triclinic, P1	Dx = 1.299 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.2390 (6) Å	Cell parameters from 1958 reflections
b = 11.456 (2) Å	θ = 3.2–26.0°
c = 11.9840 (17) Å	µ = 0.09 mm−1
α = 113.271 (15)°	T = 296 K
β = 96.534 (12)°	Block, red
γ = 95.595 (13)°	0.25 × 0.19 × 0.18 mm
V = 524.64 (16) Å3

Bruker SMART CCD area-detector diffractometer	1758 independent reflections
Radiation source: fine-focus sealed tube	587 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −5→4
Tmin = 0.979, Tmax = 0.982	k = −13→12
3321 measured reflections	l = 0→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 0.68	w = 1/[σ2(Fo2) + (0.0315P)2] where P = (Fo2 + 2Fc2)/3
1758 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.11 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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
C1	1.2639 (7)	0.1906 (3)	−0.4898 (3)	0.0923 (12)
H1A	1.1868	0.2699	−0.4786	0.138*
H1B	1.1535	0.1237	−0.5661	0.138*
H1C	1.4905	0.2007	−0.4916	0.138*
C2	1.2028 (7)	0.1556 (3)	−0.3856 (3)	0.0637 (10)
H2	1.2765	0.0820	−0.3851	0.076*
C3	1.0549 (7)	0.2191 (3)	−0.2947 (3)	0.0601 (10)
H3	0.9757	0.2916	−0.2958	0.072*
C4	1.0060 (7)	0.1857 (3)	−0.1944 (3)	0.0549 (9)
H4	1.0791	0.1129	−0.1913	0.066*
C5	0.6836 (7)	0.2802 (3)	0.0774 (2)	0.0451 (9)
C6	0.6046 (6)	0.4007 (3)	0.0883 (3)	0.0584 (9)
H6	0.6489	0.4308	0.0293	0.070*
C7	0.4654 (7)	0.4732 (3)	0.1834 (3)	0.0681 (10)
H7	0.4153	0.5520	0.1879	0.082*
C8	0.3955 (8)	0.4328 (4)	0.2745 (3)	0.0767 (11)
H8	0.3012	0.4840	0.3394	0.092*
C9	0.4679 (7)	0.3169 (3)	0.2666 (3)	0.0641 (10)
H9	0.4228	0.2883	0.3265	0.077*
C10	0.6101 (7)	0.2408 (3)	0.1686 (2)	0.0497 (9)
N1	0.8634 (6)	0.2541 (2)	−0.1088 (2)	0.0553 (7)
N2	0.8205 (5)	0.2108 (2)	−0.01925 (19)	0.0548 (8)
H2A	0.8807	0.1395	−0.0246	0.066*
N3	0.6751 (6)	0.1190 (3)	0.1671 (2)	0.0634 (8)
O1	0.5896 (6)	0.0865 (2)	0.2464 (2)	0.0933 (9)
O2	0.8241 (5)	0.05249 (18)	0.08917 (18)	0.0722 (7)

	U11	U22	U33	U12	U13	U23
C1	0.096 (3)	0.119 (3)	0.074 (2)	0.006 (2)	0.027 (2)	0.051 (2)
C2	0.075 (3)	0.063 (2)	0.062 (2)	0.006 (2)	0.0186 (19)	0.0343 (19)
C3	0.069 (3)	0.065 (3)	0.057 (2)	0.014 (2)	0.011 (2)	0.0350 (19)
C4	0.063 (2)	0.052 (2)	0.057 (2)	0.0116 (19)	0.0080 (18)	0.0305 (19)
C5	0.048 (2)	0.041 (2)	0.049 (2)	0.0052 (18)	0.0036 (17)	0.0236 (18)
C6	0.064 (2)	0.053 (2)	0.072 (2)	0.014 (2)	0.0155 (17)	0.0372 (19)
C7	0.084 (3)	0.048 (3)	0.082 (2)	0.017 (2)	0.022 (2)	0.032 (2)
C8	0.080 (3)	0.071 (3)	0.082 (3)	0.025 (2)	0.028 (2)	0.026 (2)
C9	0.079 (3)	0.063 (3)	0.059 (2)	0.016 (2)	0.0244 (18)	0.030 (2)
C10	0.057 (2)	0.045 (2)	0.056 (2)	0.0113 (19)	0.0112 (17)	0.0282 (18)
N1	0.068 (2)	0.056 (2)	0.0565 (16)	0.0143 (15)	0.0179 (15)	0.0347 (16)
N2	0.076 (2)	0.052 (2)	0.0548 (16)	0.0199 (16)	0.0241 (15)	0.0353 (15)
N3	0.073 (2)	0.073 (2)	0.0618 (18)	0.0175 (18)	0.0187 (15)	0.0431 (18)
O1	0.149 (2)	0.084 (2)	0.0911 (17)	0.0467 (17)	0.0603 (16)	0.0652 (16)
O2	0.1081 (19)	0.0611 (18)	0.0802 (14)	0.0410 (15)	0.0499 (13)	0.0479 (13)

C1—C2	1.495 (4)	C6—C7	1.356 (3)
C1—H1A	0.9600	C6—H6	0.9300
C1—H1B	0.9600	C7—C8	1.392 (4)
C1—H1C	0.9600	C7—H7	0.9300
C2—C3	1.314 (3)	C8—C9	1.361 (3)
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.429 (3)	C9—C10	1.399 (3)
C3—H3	0.9300	C9—H9	0.9300
C4—N1	1.276 (3)	C10—N3	1.442 (3)
C4—H4	0.9300	N1—N2	1.371 (3)
C5—N2	1.351 (3)	N2—H2A	0.8600
C5—C10	1.392 (3)	N3—O1	1.227 (3)
C5—C6	1.411 (3)	N3—O2	1.232 (3)
C2—C1—H1A	109.5	C5—C6—H6	119.4
C2—C1—H1B	109.5	C6—C7—C8	121.7 (3)
H1A—C1—H1B	109.5	C6—C7—H7	119.1
C2—C1—H1C	109.5	C8—C7—H7	119.1
H1A—C1—H1C	109.5	C9—C8—C7	118.7 (3)
H1B—C1—H1C	109.5	C9—C8—H8	120.7
C3—C2—C1	126.1 (3)	C7—C8—H8	120.7
C3—C2—H2	116.9	C8—C9—C10	120.1 (3)
C1—C2—H2	116.9	C8—C9—H9	119.9
C2—C3—C4	125.2 (3)	C10—C9—H9	119.9
C2—C3—H3	117.4	C5—C10—C9	121.9 (3)
C4—C3—H3	117.4	C5—C10—N3	121.8 (3)
N1—C4—C3	121.1 (3)	C9—C10—N3	116.3 (3)
N1—C4—H4	119.5	C4—N1—N2	116.1 (2)
C3—C4—H4	119.5	C5—N2—N1	119.9 (2)
N2—C5—C10	124.5 (3)	C5—N2—H2A	120.0
N2—C5—C6	119.1 (3)	N1—N2—H2A	120.0
C10—C5—C6	116.4 (3)	O1—N3—O2	121.7 (3)
C7—C6—C5	121.1 (3)	O1—N3—C10	118.9 (3)
C7—C6—H6	119.4	O2—N3—C10	119.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	2.00	2.615 (3)	127
N2—H2A···O2i	0.86	2.53	3.353 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.86	2.00	2.615 (3)	127
N2—H2A⋯O2i	0.86	2.53	3.353 (3)	160

Symmetry code: (i) .