N (1)-[(1H-Imidazol-2-yl)methyl-idene]-N (4)-phenyl-benzene-1,4-di-amine.

The title compound, C16H14N4, is non-planar with dihedral angles between the planes of the imidazole and phenyl-enedi-amine rings of 30.66 (4)° and between the planes of the phenyl-enedi-amine and N-phenyl rings of 56.63 (7)°. In the crystal, mol-ecules are connected by N-H⋯N hydrogen bonds, generating a chain extending along the b-axis direction. The crystal structure is also stabilized by C-H⋯π inter-actions between N-phenyl and imidazole rings and slipped π-π stacking inter-actions between imidazole rings [centroid-centroid distance = 3.516 (4) Å] giving an overall two-dimensional layered structure lying parallel to (010).

Related literature

For applications of Schiff bases, see: Lozier et al. (1975 ▶); Dalapati et al. (2011 ▶); Sun et al. (2012 ▶). The present work is part of an ongoing structural study of Schiff base–metal complexes, see: Faizi & Hussain (2014 ▶); Faizi & Sen (2014 ▶). For related Schiff bases and their applications, see: Thompson et al. (2012 ▶); Shue et al. (1994 ▶); Garcia et al. (2006 ▶).

Experimental

Crystal data

C16H14N4

M = 262.31

Monoclinic,

a = 15.663 (5) Å

b = 5.063 (3) Å

c = 16.800 (5) Å

β = 93.124 (5)°

V = 1330.3 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.984, T max = 0.990

11186 measured reflections

3296 independent reflections

2403 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.110

S = 1.03

3296 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2006 ▶); software used to prepare material for publication: DIAMOND.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814014238/gg2140sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014238/gg2140Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014238/gg2140Isup3.cml

CCDC reference: 1008808

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H14N4	F(000) = 552
Mr = 262.31	Dx = 1.310 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 999 reflections
a = 15.663 (5) Å	θ = 1.8–25.5°
b = 5.063 (3) Å	µ = 0.08 mm−1
c = 16.800 (5) Å	T = 100 K
β = 93.124 (5)°	Block, yellow
V = 1330.3 (10) Å3	0.15 × 0.13 × 0.10 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3296 independent reflections
Radiation source: fine-focus sealed tube	2403 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→20
Tmin = 0.984, Tmax = 0.990	k = −6→6
11186 measured reflections	l = −22→22

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) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0458P)2 + 0.404P] where P = (Fo2 + 2Fc2)/3
3296 reflections	(Δ/σ)max = 0.001
189 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.18 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	0.43125 (8)	−0.1760 (3)	0.33278 (8)	0.0214 (3)
C2	0.38397 (9)	−0.3415 (3)	0.28135 (9)	0.0282 (3)
H2	0.3891	−0.3274	0.2266	0.034*
C3	0.32914 (10)	−0.5278 (3)	0.31101 (11)	0.0352 (4)
H3	0.2974	−0.6371	0.2761	0.042*
C4	0.32145 (10)	−0.5514 (3)	0.39221 (11)	0.0337 (4)
H4	0.2861	−0.6802	0.4121	0.040*
C5	0.36660 (10)	−0.3828 (3)	0.44371 (10)	0.0308 (4)
H5	0.3607	−0.3959	0.4984	0.037*
C6	0.42048 (9)	−0.1945 (3)	0.41415 (9)	0.0275 (3)
H6	0.4498	−0.0793	0.4490	0.033*
C7	0.57160 (9)	0.0512 (3)	0.32757 (8)	0.0199 (3)
C8	0.61533 (9)	−0.1149 (3)	0.38253 (8)	0.0202 (3)
H8	0.5862	−0.2506	0.4066	0.024*
C9	0.70154 (9)	−0.0785 (3)	0.40118 (8)	0.0200 (3)
H9	0.7299	−0.1937	0.4367	0.024*
C10	0.74693 (8)	0.1273 (3)	0.36788 (8)	0.0174 (3)
C11	0.70272 (9)	0.2954 (3)	0.31390 (8)	0.0200 (3)
H11	0.7316	0.4341	0.2910	0.024*
C12	0.61719 (9)	0.2582 (3)	0.29428 (8)	0.0217 (3)
H12	0.5891	0.3725	0.2583	0.026*
C13	0.87684 (9)	0.3549 (3)	0.38064 (8)	0.0190 (3)
C14	0.96846 (8)	0.3614 (3)	0.39783 (8)	0.0173 (3)
C15	1.09852 (9)	0.2263 (3)	0.43150 (8)	0.0199 (3)
H15	1.1455	0.1208	0.4459	0.024*
C16	1.09789 (9)	0.4940 (3)	0.42150 (8)	0.0206 (3)
H16	1.1456	0.6027	0.4281	0.025*
N1	0.48649 (8)	0.0127 (3)	0.30203 (8)	0.0259 (3)
N2	0.83589 (7)	0.1392 (2)	0.38775 (6)	0.0185 (3)
N3	1.01646 (7)	0.5797 (2)	0.40025 (7)	0.0192 (3)
N4	1.01628 (7)	0.1451 (2)	0.41603 (6)	0.0181 (3)
H101	0.9981	−0.0150	0.4176	0.022*
H102	0.4709 (11)	0.072 (4)	0.2555 (11)	0.037 (5)*
H13	0.8508 (10)	0.525 (3)	0.3660 (9)	0.026 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0150 (7)	0.0220 (7)	0.0272 (7)	0.0025 (5)	0.0010 (5)	0.0033 (6)
C2	0.0250 (8)	0.0332 (9)	0.0260 (8)	−0.0003 (7)	−0.0016 (6)	0.0003 (6)
C3	0.0268 (9)	0.0310 (9)	0.0470 (10)	−0.0053 (7)	−0.0044 (7)	−0.0042 (8)
C4	0.0223 (8)	0.0287 (8)	0.0509 (11)	−0.0015 (7)	0.0083 (7)	0.0113 (7)
C5	0.0254 (8)	0.0362 (9)	0.0316 (8)	0.0038 (7)	0.0071 (6)	0.0098 (7)
C6	0.0242 (8)	0.0320 (9)	0.0262 (8)	−0.0016 (6)	0.0013 (6)	−0.0003 (6)
C7	0.0200 (7)	0.0198 (7)	0.0202 (7)	0.0003 (5)	0.0021 (5)	−0.0021 (5)
C8	0.0208 (7)	0.0172 (7)	0.0230 (7)	−0.0029 (5)	0.0038 (5)	0.0020 (5)
C9	0.0234 (7)	0.0162 (6)	0.0204 (7)	0.0010 (5)	0.0017 (5)	0.0009 (5)
C10	0.0192 (7)	0.0153 (6)	0.0177 (6)	0.0002 (5)	0.0024 (5)	−0.0037 (5)
C11	0.0246 (7)	0.0153 (6)	0.0204 (7)	−0.0026 (5)	0.0040 (5)	0.0005 (5)
C12	0.0254 (8)	0.0183 (7)	0.0213 (7)	0.0011 (6)	0.0015 (5)	0.0028 (6)
C13	0.0228 (7)	0.0165 (7)	0.0178 (6)	0.0015 (6)	0.0027 (5)	−0.0014 (5)
C14	0.0214 (7)	0.0141 (6)	0.0169 (6)	−0.0004 (5)	0.0038 (5)	−0.0007 (5)
C15	0.0180 (7)	0.0182 (7)	0.0234 (7)	−0.0001 (5)	0.0002 (5)	−0.0014 (5)
C16	0.0209 (7)	0.0176 (7)	0.0235 (7)	−0.0028 (5)	0.0020 (5)	−0.0018 (5)
N1	0.0198 (6)	0.0314 (7)	0.0260 (7)	−0.0040 (5)	−0.0027 (5)	0.0092 (6)
N2	0.0208 (6)	0.0169 (6)	0.0179 (6)	−0.0023 (5)	0.0025 (4)	−0.0010 (4)
N3	0.0200 (6)	0.0149 (6)	0.0226 (6)	−0.0015 (4)	0.0018 (5)	−0.0013 (4)
N4	0.0208 (6)	0.0117 (5)	0.0220 (6)	−0.0024 (4)	0.0022 (4)	−0.0001 (4)

C1—C2	1.388 (2)	C9—H9	0.9300
C1—C6	1.390 (2)	C10—C11	1.3990 (19)
C1—N1	1.4060 (19)	C10—N2	1.4163 (18)
C2—C3	1.386 (2)	C11—C12	1.375 (2)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.381 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—N2	1.2757 (18)
C4—C5	1.383 (2)	C13—C14	1.449 (2)
C4—H4	0.9300	C13—H13	0.976 (17)
C5—C6	1.383 (2)	C14—N3	1.3358 (18)
C5—H5	0.9300	C14—N4	1.3526 (18)
C6—H6	0.9300	C15—N4	1.3636 (18)
C7—N1	1.3918 (18)	C15—C16	1.366 (2)
C7—C8	1.400 (2)	C15—H15	0.9300
C7—C12	1.402 (2)	C16—N3	1.3757 (18)
C8—C9	1.382 (2)	C16—H16	0.9300
C8—H8	0.9300	N1—H102	0.860 (19)
C9—C10	1.3957 (19)	N4—H101	0.8600
C2—C1—C6	118.84 (13)	C9—C10—N2	116.95 (12)
C2—C1—N1	119.97 (14)	C11—C10—N2	124.95 (12)
C6—C1—N1	121.15 (13)	C12—C11—C10	120.90 (13)
C3—C2—C1	120.45 (15)	C12—C11—H11	119.6
C3—C2—H2	119.8	C10—C11—H11	119.5
C1—C2—H2	119.8	C11—C12—C7	121.16 (13)
C4—C3—C2	120.21 (16)	C11—C12—H12	119.4
C4—C3—H3	119.9	C7—C12—H12	119.4
C2—C3—H3	119.9	N2—C13—C14	119.90 (13)
C3—C4—C5	119.69 (15)	N2—C13—H13	124.9 (9)
C3—C4—H4	120.2	C14—C13—H13	115.2 (9)
C5—C4—H4	120.2	N3—C14—N4	111.05 (12)
C4—C5—C6	120.16 (15)	N3—C14—C13	125.08 (12)
C4—C5—H5	119.9	N4—C14—C13	123.84 (12)
C6—C5—H5	119.9	N4—C15—C16	105.97 (13)
C5—C6—C1	120.58 (15)	N4—C15—H15	127.0
C5—C6—H6	119.7	C16—C15—H15	127.0
C1—C6—H6	119.7	C15—C16—N3	110.19 (13)
N1—C7—C8	123.04 (13)	C15—C16—H16	124.9
N1—C7—C12	118.81 (13)	N3—C16—H16	124.9
C8—C7—C12	118.08 (13)	C7—N1—C1	125.46 (13)
C9—C8—C7	120.43 (13)	C7—N1—H102	116.8 (12)
C9—C8—H8	119.8	C1—N1—H102	114.9 (12)
C7—C8—H8	119.8	C13—N2—C10	120.49 (12)
C8—C9—C10	121.43 (13)	C14—N3—C16	105.04 (12)
C8—C9—H9	119.3	C14—N4—C15	107.74 (11)
C10—C9—H9	119.3	C14—N4—H101	126.1
C9—C10—C11	117.97 (13)	C15—N4—H101	126.1
C6—C1—C2—C3	−2.1 (2)	C8—C7—C12—C11	1.0 (2)
N1—C1—C2—C3	−179.81 (14)	N2—C13—C14—N3	−172.90 (12)
C1—C2—C3—C4	−0.4 (2)	N2—C13—C14—N4	5.0 (2)
C2—C3—C4—C5	2.1 (2)	N4—C15—C16—N3	0.14 (16)
C3—C4—C5—C6	−1.2 (2)	C8—C7—N1—C1	6.8 (2)
C4—C5—C6—C1	−1.3 (2)	C12—C7—N1—C1	−176.26 (14)
C2—C1—C6—C5	3.0 (2)	C2—C1—N1—C7	−130.27 (16)
N1—C1—C6—C5	−179.36 (14)	C6—C1—N1—C7	52.1 (2)
N1—C7—C8—C9	175.16 (13)	C14—C13—N2—C10	−177.30 (11)
C12—C7—C8—C9	−1.8 (2)	C9—C10—N2—C13	−158.92 (12)
C7—C8—C9—C10	1.8 (2)	C11—C10—N2—C13	25.31 (19)
C8—C9—C10—C11	−0.8 (2)	N4—C14—N3—C16	−0.39 (14)
C8—C9—C10—N2	−176.86 (12)	C13—C14—N3—C16	177.74 (12)
C9—C10—C11—C12	−0.07 (19)	C15—C16—N3—C14	0.15 (15)
N2—C10—C11—C12	175.65 (12)	N3—C14—N4—C15	0.49 (15)
C10—C11—C12—C7	−0.1 (2)	C13—C14—N4—C15	−177.67 (12)
N1—C7—C12—C11	−176.13 (13)	C16—C15—N4—C14	−0.37 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H101···N3i	0.86	2.09	2.875 (3)	151
C2—H2···Cg1ii	0.93	2.83	3.691 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N3/N4/C14–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H101⋯N3i	0.86	2.09	2.875 (3)	151
C2—H2⋯Cg1ii	0.93	2.83	3.691 (3)	155

Symmetry codes: (i) ; (ii) .