(E)-4-{[(Morpholin-4-yl)imino]-meth-yl}benzo-nitrile.

In the title compound, C12H13N3O, the morpholine ring adopts a chair conformation and its mean plane is inclined to that of the benzene ring by 16.78 (12)°. The N-N=C-C bridge, which has an E conformation, has a torsion angle of 173.80 (19)°. In the crystal, mol-ecules stack along the a axis but there are no significant inter-molecular inter-actions present.

Related literature

For background to the importance of Schiff bases, see: Dhar & Taploo (1982 ▶); Zheng et al. (2009 ▶); Guzen et al. (2007 ▶); Asif (2014 ▶); Hisaindee et al. (2013 ▶). For a related structure, see: Akkurt et al. (2013 ▶).

Experimental

Crystal data

C12H13N3O

M = 215.25

Monoclinic,

a = 4.1054 (3) Å

b = 12.0509 (8) Å

c = 22.9972 (19) Å

β = 91.087 (6)°

V = 1137.55 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.54 × 0.24 × 0.08 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.971, T max = 0.994

6956 measured reflections

2394 independent reflections

878 reflections with I > 2σ(I)

R int = 0.229

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.094

S = 0.89

2394 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.11 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814014020/su2744sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014020/su2744Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014020/su2744Isup3.cml

CCDC reference: 1008300

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

C12H13N3O	F(000) = 456
Mr = 215.25	Dx = 1.257 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4198 reflections
a = 4.1054 (3) Å	θ = 1.7–27.1°
b = 12.0509 (8) Å	µ = 0.08 mm−1
c = 22.9972 (19) Å	T = 296 K
β = 91.087 (6)°	Prism, light yellow
V = 1137.55 (15) Å3	0.54 × 0.24 × 0.08 mm
Z = 4

Stoe IPDS 2 diffractometer	2394 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	878 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.229
Detector resolution: 6.67 pixels mm-1	θmax = 26.7°, θmin = 1.8°
rotation method scans	h = −5→5
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→15
Tmin = 0.971, Tmax = 0.994	l = −29→28
6956 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.021P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max < 0.001
2394 reflections	Δρmax = 0.12 e Å−3
146 parameters	Δρmin = −0.11 e Å−3

Experimental. Spectropscopic data for the title compound: IR (KBr, cm-1): 1604 (Schiff base C=N), 2214 (nitrile CN). 1H-NMR (250 MHz, CDCl3), δ (p.p.m.): 3.18–3.22 (CH2 morpholine ring, m, 4H), 3.83–3.87 (CH2 morpholine ring, m, 4H), 7.48 (HC=N, s, 1H), 7.54 (ArH, d, J=8.4 Hz, 2H), 7.62 (ArH, d, J=8.2 Hz, 2H). 13C-NMR (62.9 MHz, CDCl3), δ (p.p.m.): 51.3 (CH2N), 66.2 (CH2O), 110.7, 119.0, 126.2, 132.3, 132.6 (aromatic carbons and nitrile), 140.4 (C=N).

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	0.3333 (4)	0.7856 (2)	0.26705 (10)	0.0934 (9)
N1	0.5804 (4)	0.92897 (19)	0.18135 (10)	0.0661 (9)
N2	0.6187 (4)	0.9921 (2)	0.13245 (9)	0.0642 (9)
N3	0.9567 (8)	1.4147 (2)	−0.10077 (15)	0.1297 (14)
C1	0.4673 (6)	0.8185 (2)	0.16642 (12)	0.0744 (11)
C2	0.5031 (6)	0.7434 (3)	0.21844 (15)	0.0919 (15)
C3	0.4574 (7)	0.8916 (3)	0.28163 (13)	0.0920 (14)
C4	0.4229 (6)	0.9736 (2)	0.23245 (12)	0.0739 (11)
C5	0.5801 (5)	1.0975 (3)	0.13421 (11)	0.0671 (10)
C6	0.6545 (6)	1.1639 (2)	0.08316 (12)	0.0621 (10)
C7	0.5920 (6)	1.2770 (2)	0.08316 (13)	0.0797 (12)
C8	0.6662 (7)	1.3426 (2)	0.03595 (15)	0.0865 (14)
C9	0.8027 (6)	1.2960 (3)	−0.01231 (14)	0.0732 (11)
C10	0.8635 (6)	1.1833 (2)	−0.01327 (14)	0.0864 (12)
C11	0.7892 (6)	1.1192 (2)	0.03383 (13)	0.0817 (12)
C12	0.8858 (8)	1.3627 (3)	−0.06134 (17)	0.0941 (16)
H1A	0.59330	0.78940	0.13460	0.0890*
H1B	0.24050	0.82150	0.15390	0.0890*
H2A	0.41920	0.67040	0.20860	0.1100*
H2B	0.73230	0.73570	0.22870	0.1100*
H3A	0.68600	0.88470	0.29250	0.1100*
H3B	0.34310	0.91970	0.31510	0.1100*
H4A	0.19410	0.98700	0.22380	0.0890*
H4B	0.52330	1.04350	0.24350	0.0890*
H5	0.50530	1.13130	0.16780	0.0800*
H7	0.49840	1.30930	0.11550	0.0950*
H8	0.62370	1.41830	0.03690	0.1040*
H10	0.95490	1.15100	−0.04590	0.1030*
H11	0.83060	1.04340	0.03250	0.0980*

	U11	U22	U33	U12	U13	U23
O1	0.0852 (12)	0.1033 (19)	0.0918 (16)	−0.0208 (12)	0.0086 (12)	0.0200 (14)
N1	0.0643 (13)	0.0668 (18)	0.0673 (15)	−0.0065 (11)	0.0016 (12)	0.0045 (14)
N2	0.0627 (12)	0.0629 (17)	0.0669 (15)	−0.0007 (12)	0.0013 (11)	0.0014 (13)
N3	0.191 (3)	0.086 (2)	0.112 (2)	−0.031 (2)	−0.002 (2)	0.0243 (19)
C1	0.0715 (16)	0.065 (2)	0.087 (2)	−0.0054 (14)	0.0074 (14)	0.0055 (17)
C2	0.0829 (18)	0.083 (3)	0.110 (3)	−0.0068 (17)	0.0039 (18)	0.022 (2)
C3	0.0882 (19)	0.115 (3)	0.073 (2)	−0.023 (2)	0.0043 (16)	0.015 (2)
C4	0.0708 (16)	0.082 (2)	0.069 (2)	−0.0124 (15)	0.0029 (15)	−0.0037 (17)
C5	0.0664 (16)	0.075 (2)	0.0600 (18)	0.0006 (15)	0.0063 (13)	−0.0042 (16)
C6	0.0647 (15)	0.0553 (19)	0.066 (2)	0.0010 (14)	−0.0046 (14)	−0.0092 (16)
C7	0.104 (2)	0.062 (2)	0.073 (2)	0.0079 (17)	−0.0001 (17)	−0.0130 (17)
C8	0.119 (2)	0.049 (2)	0.091 (3)	0.0085 (17)	−0.013 (2)	−0.0018 (19)
C9	0.0852 (18)	0.059 (2)	0.075 (2)	−0.0054 (16)	−0.0061 (17)	0.0007 (18)
C10	0.118 (2)	0.064 (2)	0.078 (2)	0.0066 (18)	0.0245 (18)	0.0028 (18)
C11	0.112 (2)	0.053 (2)	0.081 (2)	0.0108 (16)	0.0230 (18)	−0.0010 (18)
C12	0.125 (3)	0.068 (2)	0.089 (3)	−0.0177 (19)	−0.004 (2)	0.007 (2)

O1—C2	1.423 (4)	C9—C12	1.431 (5)
O1—C3	1.413 (4)	C10—C11	1.370 (4)
N1—N2	1.369 (3)	C1—H1A	0.9700
N1—C1	1.449 (3)	C1—H1B	0.9700
N1—C4	1.455 (3)	C2—H2A	0.9700
N2—C5	1.281 (4)	C2—H2B	0.9700
N3—C12	1.144 (5)	C3—H3A	0.9700
C1—C2	1.505 (4)	C3—H3B	0.9700
C3—C4	1.507 (4)	C4—H4A	0.9700
C5—C6	1.458 (4)	C4—H4B	0.9700
C6—C7	1.387 (3)	C5—H5	0.9300
C6—C11	1.381 (4)	C7—H7	0.9300
C7—C8	1.382 (4)	C8—H8	0.9300
C8—C9	1.373 (5)	C10—H10	0.9300
C9—C10	1.381 (4)	C11—H11	0.9300
C2—O1—C3	109.3 (2)	O1—C2—H2A	109.00
N2—N1—C1	110.9 (2)	O1—C2—H2B	109.00
N2—N1—C4	121.2 (2)	C1—C2—H2A	109.00
C1—N1—C4	112.68 (19)	C1—C2—H2B	109.00
N1—N2—C5	120.6 (2)	H2A—C2—H2B	108.00
N1—C1—C2	109.8 (2)	O1—C3—H3A	109.00
O1—C2—C1	111.6 (3)	O1—C3—H3B	109.00
O1—C3—C4	112.7 (2)	C4—C3—H3A	109.00
N1—C4—C3	109.1 (2)	C4—C3—H3B	109.00
N2—C5—C6	119.4 (2)	H3A—C3—H3B	108.00
C5—C6—C7	119.9 (3)	N1—C4—H4A	110.00
C5—C6—C11	122.7 (2)	N1—C4—H4B	110.00
C7—C6—C11	117.4 (2)	C3—C4—H4A	110.00
C6—C7—C8	121.3 (3)	C3—C4—H4B	110.00
C7—C8—C9	120.0 (3)	H4A—C4—H4B	108.00
C8—C9—C10	119.5 (3)	N2—C5—H5	120.00
C8—C9—C12	120.9 (3)	C6—C5—H5	120.00
C10—C9—C12	119.6 (3)	C6—C7—H7	119.00
C9—C10—C11	119.9 (3)	C8—C7—H7	119.00
C6—C11—C10	121.9 (2)	C7—C8—H8	120.00
N3—C12—C9	178.8 (4)	C9—C8—H8	120.00
N1—C1—H1A	110.00	C9—C10—H10	120.00
N1—C1—H1B	110.00	C11—C10—H10	120.00
C2—C1—H1A	110.00	C6—C11—H11	119.00
C2—C1—H1B	110.00	C10—C11—H11	119.00
H1A—C1—H1B	108.00
C2—O1—C3—C4	59.5 (3)	N2—C5—C6—C11	−5.0 (4)
C3—O1—C2—C1	−59.4 (3)	C5—C6—C7—C8	178.6 (2)
C4—N1—N2—C5	14.6 (3)	C11—C6—C7—C8	−0.9 (4)
C1—N1—N2—C5	150.2 (2)	C5—C6—C11—C10	−178.7 (2)
N2—N1—C1—C2	166.62 (18)	C7—C6—C11—C10	0.9 (4)
C4—N1—C1—C2	−53.9 (3)	C6—C7—C8—C9	0.4 (4)
N2—N1—C4—C3	−172.2 (2)	C7—C8—C9—C10	0.3 (4)
C1—N1—C4—C3	52.9 (3)	C7—C8—C9—C12	−179.1 (3)
N1—N2—C5—C6	173.80 (19)	C8—C9—C10—C11	−0.4 (4)
N1—C1—C2—O1	56.8 (3)	C12—C9—C10—C11	179.0 (3)
O1—C3—C4—N1	−55.9 (3)	C9—C10—C11—C6	−0.2 (4)
N2—C5—C6—C7	175.5 (2)