(Z)-2-Amino-3-[(E)-benzyl-ideneamino]but-2-enedinitrile.

The asymmetric unit of the title compound, C(11)H(8)N(4), contains two independent mol-ecules. In the crystal structure, inter-molecular N-H⋯N hydrogen bonds link mol-ecules into ribbons extended in the [100] direction.

Related literature

For some properties of Schiff base ligands, see: Arun, Robinson et al. (2009 ▶); Arun, Sridevi et al. (2009 ▶). For related structures, see: MacLachlan et al. (1996 ▶); Mague & Eduok (2000 ▶); Varghese et al. (2009 ▶).

Experimental

Crystal data

C11H8N4

M = 196.21

Monoclinic,

a = 6.9569 (19) Å

b = 22.796 (6) Å

c = 13.516 (4) Å

β = 100.983 (5)°

V = 2104.2 (10) Å3

Z = 8

Mo Kα radiation radiation

μ = 0.08 mm−1

T = 298 K

0.42 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.980, T max = 0.984

12239 measured reflections

4173 independent reflections

3216 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.106

wR(F 2) = 0.214

S = 1.29

4173 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010873/cv2533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010873/cv2533Isup2.hkl

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

C11H8N4	F(000) = 816
Mr = 196.21	Dx = 1.239 Mg m−3
Monoclinic, P21/c	Mo Kα radiation radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4803 reflections
a = 6.9569 (19) Å	θ = 2.4–26.1°
b = 22.796 (6) Å	µ = 0.08 mm−1
c = 13.516 (4) Å	T = 298 K
β = 100.983 (5)°	Rod, yellow
V = 2104.2 (10) Å3	0.42 × 0.18 × 0.18 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	4173 independent reflections
Radiation source: fine-focus sealed tube	3216 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 26.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −8→8
Tmin = 0.980, Tmax = 0.984	k = −28→23
12239 measured reflections	l = −16→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.106	H-atom parameters constrained
wR(F2) = 0.214	w = 1/[σ2(Fo2) + (0.0476P)2 + 1.6604P] where P = (Fo2 + 2Fc2)/3
S = 1.29	(Δ/σ)max < 0.001
4173 reflections	Δρmax = 0.22 e Å−3
272 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (6)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.3264 (5)	0.39467 (14)	0.3626 (2)	0.0398 (8)
C2	0.3971 (6)	0.34110 (16)	0.3379 (3)	0.0590 (11)
H2	0.5196	0.3387	0.3202	0.071*
C3	0.2851 (8)	0.29092 (19)	0.3397 (4)	0.0772 (14)
H3	0.3324	0.2548	0.3229	0.093*
C4	0.1054 (8)	0.2944 (2)	0.3661 (4)	0.0792 (15)
H4	0.0313	0.2606	0.3677	0.095*
C5	0.0339 (6)	0.3473 (2)	0.3902 (3)	0.0673 (12)
H5	−0.0887	0.3494	0.4078	0.081*
C6	0.1427 (5)	0.39773 (17)	0.3883 (3)	0.0501 (9)
H6	0.0933	0.4337	0.4043	0.060*
C7	0.4454 (5)	0.44731 (14)	0.3591 (3)	0.0388 (8)
H7	0.5684	0.4436	0.3422	0.047*
C8	0.5013 (4)	0.54703 (14)	0.3760 (2)	0.0366 (8)
C9	0.4227 (5)	0.60037 (14)	0.3899 (3)	0.0397 (8)
C10	0.6996 (5)	0.54341 (15)	0.3605 (3)	0.0469 (9)
C11	0.5356 (5)	0.65316 (15)	0.3859 (3)	0.0459 (9)
N1	0.3855 (4)	0.49769 (11)	0.3784 (2)	0.0367 (7)
N2	0.2412 (4)	0.60811 (13)	0.4084 (2)	0.0558 (9)
H2A	0.1673	0.5783	0.4122	0.067*
H2B	0.1991	0.6429	0.4165	0.067*
N3	0.8559 (5)	0.53781 (16)	0.3485 (3)	0.0764 (12)
N4	0.6208 (5)	0.69534 (14)	0.3808 (3)	0.0693 (11)
C12	0.2008 (5)	0.53605 (15)	0.1295 (3)	0.0452 (9)
C13	0.3849 (5)	0.53053 (17)	0.1052 (3)	0.0550 (10)
H13	0.4312	0.4934	0.0933	0.066*
C14	0.4994 (7)	0.5783 (2)	0.0985 (4)	0.0736 (13)
H14	0.6224	0.5739	0.0819	0.088*
C15	0.4310 (8)	0.6331 (2)	0.1165 (4)	0.0823 (16)
H15	0.5078	0.6659	0.1109	0.099*
C16	0.2515 (9)	0.64021 (18)	0.1425 (4)	0.0821 (16)
H16	0.2090	0.6775	0.1562	0.098*
C17	0.1334 (7)	0.59197 (17)	0.1484 (3)	0.0639 (12)
H17	0.0104	0.5967	0.1648	0.077*
C18	0.0775 (5)	0.48496 (15)	0.1349 (3)	0.0450 (9)
H18	−0.0432	0.4899	0.1538	0.054*
C19	0.0133 (4)	0.38528 (14)	0.1179 (3)	0.0379 (8)
C20	0.0863 (5)	0.33203 (15)	0.0987 (3)	0.0416 (8)
C21	−0.1801 (5)	0.38947 (15)	0.1396 (3)	0.0450 (9)
C22	−0.0336 (6)	0.28020 (17)	0.0983 (3)	0.0540 (10)
N5	0.1316 (4)	0.43361 (12)	0.1143 (2)	0.0396 (7)
N6	0.2648 (4)	0.32364 (12)	0.0767 (2)	0.0555 (9)
H6A	0.3410	0.3531	0.0741	0.067*
H6B	0.3028	0.2888	0.0652	0.067*
N7	−0.3334 (4)	0.39419 (15)	0.1568 (3)	0.0660 (10)
N8	−0.1258 (5)	0.23914 (15)	0.0977 (3)	0.0809 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0501 (19)	0.0328 (18)	0.0338 (19)	−0.0032 (15)	0.0015 (15)	0.0035 (15)
C2	0.070 (3)	0.036 (2)	0.069 (3)	0.0021 (19)	0.007 (2)	0.002 (2)
C3	0.112 (4)	0.035 (2)	0.079 (3)	−0.002 (3)	0.006 (3)	0.005 (2)
C4	0.110 (4)	0.053 (3)	0.070 (3)	−0.038 (3)	0.006 (3)	0.010 (2)
C5	0.067 (3)	0.069 (3)	0.064 (3)	−0.026 (2)	0.009 (2)	0.003 (2)
C6	0.056 (2)	0.042 (2)	0.052 (2)	−0.0072 (17)	0.0069 (18)	0.0007 (18)
C7	0.0369 (17)	0.0353 (19)	0.045 (2)	0.0016 (14)	0.0104 (15)	−0.0001 (15)
C8	0.0334 (16)	0.0365 (19)	0.0387 (19)	−0.0038 (14)	0.0042 (14)	−0.0004 (15)
C9	0.0413 (18)	0.0328 (18)	0.044 (2)	−0.0093 (15)	0.0064 (15)	0.0002 (16)
C10	0.044 (2)	0.039 (2)	0.059 (2)	−0.0075 (16)	0.0116 (17)	−0.0016 (17)
C11	0.051 (2)	0.034 (2)	0.050 (2)	−0.0021 (17)	0.0028 (17)	0.0064 (17)
N1	0.0324 (13)	0.0315 (15)	0.0451 (17)	−0.0031 (12)	0.0045 (12)	0.0013 (13)
N2	0.0506 (17)	0.0364 (17)	0.085 (3)	−0.0009 (14)	0.0238 (17)	−0.0085 (16)
N3	0.0413 (18)	0.066 (2)	0.127 (4)	−0.0080 (17)	0.030 (2)	−0.011 (2)
N4	0.078 (2)	0.038 (2)	0.089 (3)	−0.0181 (18)	0.010 (2)	0.0034 (18)
C12	0.057 (2)	0.0302 (19)	0.042 (2)	−0.0028 (16)	−0.0046 (17)	0.0012 (16)
C13	0.060 (2)	0.048 (2)	0.057 (3)	−0.0086 (19)	0.010 (2)	0.0004 (19)
C14	0.085 (3)	0.058 (3)	0.077 (3)	−0.026 (2)	0.013 (3)	−0.002 (2)
C15	0.109 (4)	0.060 (3)	0.070 (3)	−0.038 (3)	−0.005 (3)	0.007 (3)
C16	0.125 (4)	0.022 (2)	0.084 (4)	−0.002 (3)	−0.018 (3)	0.002 (2)
C17	0.078 (3)	0.040 (2)	0.067 (3)	0.009 (2)	−0.006 (2)	−0.006 (2)
C18	0.0454 (19)	0.044 (2)	0.045 (2)	0.0033 (16)	0.0091 (16)	−0.0035 (17)
C19	0.0361 (16)	0.0337 (19)	0.043 (2)	−0.0032 (14)	0.0058 (15)	0.0029 (15)
C20	0.0466 (19)	0.0349 (19)	0.043 (2)	−0.0065 (15)	0.0083 (16)	−0.0014 (16)
C21	0.0450 (19)	0.038 (2)	0.051 (2)	−0.0029 (16)	0.0064 (17)	−0.0022 (17)
C22	0.054 (2)	0.041 (2)	0.070 (3)	−0.0045 (18)	0.017 (2)	−0.006 (2)
N5	0.0410 (15)	0.0309 (15)	0.0456 (17)	−0.0022 (12)	0.0050 (13)	−0.0021 (13)
N6	0.0520 (18)	0.0287 (16)	0.093 (3)	0.0009 (14)	0.0315 (18)	−0.0022 (16)
N7	0.0443 (18)	0.070 (2)	0.088 (3)	−0.0002 (17)	0.0241 (18)	0.002 (2)
N8	0.072 (2)	0.046 (2)	0.127 (4)	−0.0218 (19)	0.026 (2)	−0.005 (2)

C1—C2	1.381 (5)	C12—C13	1.387 (5)
C1—C6	1.389 (5)	C12—C17	1.398 (5)
C1—C7	1.464 (4)	C12—C18	1.457 (5)
C2—C3	1.387 (6)	C13—C14	1.362 (5)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.365 (7)	C14—C15	1.375 (6)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.369 (6)	C15—C16	1.370 (7)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.378 (5)	C16—C17	1.384 (6)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—N1	1.266 (4)	C18—N5	1.276 (4)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.360 (4)	C19—C20	1.360 (4)
C8—N1	1.387 (4)	C19—N5	1.382 (4)
C8—C10	1.437 (4)	C19—C21	1.434 (4)
C9—N2	1.345 (4)	C20—N6	1.344 (4)
C9—C11	1.443 (4)	C20—C22	1.446 (5)
C10—N3	1.136 (4)	C21—N7	1.139 (4)
C11—N4	1.138 (4)	C22—N8	1.134 (4)
N2—H2A	0.8600	N6—H6A	0.8600
N2—H2B	0.8600	N6—H6B	0.8600
C2—C1—C6	119.5 (3)	C13—C12—C17	118.9 (4)
C2—C1—C7	119.2 (3)	C13—C12—C18	121.2 (3)
C6—C1—C7	121.3 (3)	C17—C12—C18	119.9 (4)
C1—C2—C3	119.9 (4)	C14—C13—C12	121.4 (4)
C1—C2—H2	120.1	C14—C13—H13	119.3
C3—C2—H2	120.1	C12—C13—H13	119.3
C4—C3—C2	120.1 (4)	C13—C14—C15	119.2 (5)
C4—C3—H3	119.9	C13—C14—H14	120.4
C2—C3—H3	119.9	C15—C14—H14	120.4
C3—C4—C5	120.3 (4)	C16—C15—C14	121.1 (4)
C3—C4—H4	119.8	C16—C15—H15	119.5
C5—C4—H4	119.8	C14—C15—H15	119.5
C4—C5—C6	120.3 (4)	C15—C16—C17	120.1 (4)
C4—C5—H5	119.8	C15—C16—H16	120.0
C6—C5—H5	119.8	C17—C16—H16	120.0
C5—C6—C1	119.8 (4)	C16—C17—C12	119.4 (4)
C5—C6—H6	120.1	C16—C17—H17	120.3
C1—C6—H6	120.1	C12—C17—H17	120.3
N1—C7—C1	121.8 (3)	N5—C18—C12	121.4 (3)
N1—C7—H7	119.1	N5—C18—H18	119.3
C1—C7—H7	119.1	C12—C18—H18	119.3
C9—C8—N1	118.1 (3)	C20—C19—N5	117.3 (3)
C9—C8—C10	119.6 (3)	C20—C19—C21	119.9 (3)
N1—C8—C10	122.3 (3)	N5—C19—C21	122.9 (3)
N2—C9—C8	124.0 (3)	N6—C20—C19	124.3 (3)
N2—C9—C11	115.7 (3)	N6—C20—C22	116.1 (3)
C8—C9—C11	120.3 (3)	C19—C20—C22	119.6 (3)
N3—C10—C8	176.8 (4)	N7—C21—C19	178.4 (4)
N4—C11—C9	178.2 (4)	N8—C22—C20	179.1 (4)
C7—N1—C8	121.0 (3)	C18—N5—C19	121.4 (3)
C9—N2—H2A	120.0	C20—N6—H6A	120.0
C9—N2—H2B	120.0	C20—N6—H6B	120.0
H2A—N2—H2B	120.0	H6A—N6—H6B	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3i	0.86	2.36	3.096 (4)	144
N2—H2B···N8ii	0.86	2.25	3.090 (5)	165
N6—H6A···N7iii	0.86	2.51	3.228 (5)	142
N6—H6B···N4iv	0.86	2.28	3.057 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N3i	0.86	2.36	3.096 (4)	144
N2—H2B⋯N8ii	0.86	2.25	3.090 (5)	165
N6—H6A⋯N7iii	0.86	2.51	3.228 (5)	142
N6—H6B⋯N4iv	0.86	2.28	3.057 (4)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .