(E)-2-(4-Nitro-benzyl-ideneamino)benzamide.

The title compound, C(14)H(11)N(3)O(3), adopts an E conformation, with a dihedral angle of 41.8 (1) ° between the mean planes of the two benzene rings. One of the amino H atoms forms an intra-molecular hydrogen bond with the amide N atom, while the other H atom forms an inter-molecular hydrogen bond with the carbonyl O atom of an adjacent mol-ecule, forming dimers about inversion centers. A non-classical inter-molecular C-H⋯O hydrogen bond also links adjacent mol-ecules into dimers.

Related literature

For Schiff bases complexes with metal ions, see: Kannan & Ramesh (2006 ▶); Lv et al. (2006 ▶); Maurya et al. (2006 ▶); Parekh et al. (2006 ▶); Vanco et al. (2004 ▶).

Experimental

Crystal data

C14H11N3O3

M = 269.26

Monoclinic,

a = 7.3863 (2) Å

b = 12.2657 (3) Å

c = 14.1414 (4) Å

β = 97.248 (1)°

V = 1270.95 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.45 × 0.29 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

9505 measured reflections

2278 independent reflections

1809 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.04

2278 reflections

190 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902203X/pv2166sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902203X/pv2166Isup2.hkl

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

C14H11N3O3	F(000) = 560
Mr = 269.26	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Melting point = 457–458 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.3863 (2) Å	Cell parameters from 3148 reflections
b = 12.2657 (3) Å	θ = 2.2–25.8°
c = 14.1414 (4) Å	µ = 0.10 mm−1
β = 97.248 (1)°	T = 296 K
V = 1270.95 (6) Å3	Block, yellow
Z = 4	0.45 × 0.29 × 0.16 mm

Bruker SMART CCD area-detector diffractometer	1809 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 25.2°, θmin = 2.2°
φ and ω scans	h = −8→8
9505 measured reflections	k = −14→14
2278 independent reflections	l = −16→16

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0436P)2 + 0.1992P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2278 reflections	Δρmax = 0.14 e Å−3
190 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.046 (3)

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
N2	0.29424 (15)	0.81888 (9)	0.04882 (9)	0.0480 (3)
O2	0.66701 (16)	0.86265 (9)	0.54680 (8)	0.0669 (3)
O3	−0.03944 (14)	0.58880 (8)	−0.10923 (7)	0.0556 (3)
C9	0.39628 (18)	0.86357 (11)	0.21085 (11)	0.0459 (4)
C2	0.10787 (17)	0.76078 (11)	−0.09651 (10)	0.0413 (3)
C1	0.06905 (17)	0.64827 (11)	−0.06033 (10)	0.0412 (3)
N3	0.66097 (17)	0.79210 (10)	0.48528 (10)	0.0525 (3)
C12	0.56915 (18)	0.81749 (11)	0.38992 (10)	0.0445 (4)
C7	0.20752 (18)	0.84286 (11)	−0.04369 (11)	0.0445 (3)
N1	0.15232 (19)	0.61634 (11)	0.02351 (10)	0.0536 (4)
C8	0.30111 (19)	0.88799 (12)	0.11590 (11)	0.0503 (4)
H8A	0.2447	0.9554	0.1046	0.060*
C14	0.3976 (2)	0.93889 (11)	0.28377 (11)	0.0521 (4)
H14A	0.3381	1.0053	0.2721	0.063*
C13	0.4860 (2)	0.91691 (11)	0.37357 (11)	0.0518 (4)
H13A	0.4892	0.9684	0.4220	0.062*
C3	0.0323 (2)	0.78476 (12)	−0.18910 (11)	0.0497 (4)
H3A	−0.0348	0.7314	−0.2248	0.060*
C11	0.5690 (2)	0.74035 (12)	0.31915 (13)	0.0540 (4)
H11A	0.6261	0.6734	0.3318	0.065*
C10	0.4840 (2)	0.76367 (12)	0.23011 (12)	0.0552 (4)
H10A	0.4844	0.7124	0.1817	0.066*
O1	0.72849 (17)	0.70200 (9)	0.49945 (9)	0.0717 (4)
C4	0.0538 (2)	0.88540 (14)	−0.22967 (12)	0.0592 (4)
H4A	0.0017	0.8994	−0.2918	0.071*
C5	0.1527 (2)	0.96491 (14)	−0.17769 (13)	0.0645 (5)
H5A	0.1680	1.0329	−0.2047	0.077*
C6	0.2289 (2)	0.94391 (12)	−0.08568 (13)	0.0590 (4)
H6A	0.2957	0.9981	−0.0510	0.071*
H1A	0.226 (2)	0.6618 (14)	0.0573 (13)	0.067 (5)*
H1B	0.121 (2)	0.5508 (15)	0.0458 (11)	0.060 (5)*

	U11	U22	U33	U12	U13	U23
N2	0.0529 (7)	0.0391 (6)	0.0509 (8)	−0.0056 (5)	0.0025 (6)	−0.0035 (6)
O2	0.0898 (8)	0.0617 (7)	0.0489 (7)	−0.0009 (6)	0.0074 (6)	−0.0088 (6)
O3	0.0673 (6)	0.0468 (6)	0.0495 (7)	−0.0128 (5)	−0.0050 (5)	−0.0018 (5)
C9	0.0473 (7)	0.0400 (7)	0.0507 (9)	−0.0063 (6)	0.0079 (6)	−0.0063 (7)
C2	0.0418 (7)	0.0405 (7)	0.0421 (8)	0.0023 (5)	0.0079 (6)	0.0007 (6)
C1	0.0440 (7)	0.0399 (7)	0.0404 (8)	−0.0003 (6)	0.0076 (6)	−0.0039 (6)
N3	0.0589 (7)	0.0471 (7)	0.0530 (9)	−0.0034 (6)	0.0135 (6)	−0.0007 (7)
C12	0.0464 (7)	0.0428 (8)	0.0452 (9)	−0.0052 (6)	0.0091 (6)	−0.0023 (7)
C7	0.0477 (7)	0.0388 (7)	0.0472 (9)	0.0022 (6)	0.0066 (6)	0.0012 (6)
N1	0.0678 (8)	0.0412 (7)	0.0484 (8)	−0.0137 (6)	−0.0058 (7)	0.0056 (6)
C8	0.0544 (8)	0.0396 (7)	0.0568 (10)	−0.0013 (6)	0.0067 (7)	−0.0037 (7)
C14	0.0666 (9)	0.0358 (7)	0.0544 (10)	0.0019 (6)	0.0098 (8)	−0.0051 (7)
C13	0.0696 (9)	0.0390 (8)	0.0482 (10)	−0.0030 (7)	0.0130 (8)	−0.0091 (7)
C3	0.0507 (8)	0.0529 (8)	0.0456 (9)	0.0022 (6)	0.0066 (7)	0.0024 (7)
C11	0.0569 (8)	0.0431 (8)	0.0610 (10)	0.0080 (6)	0.0041 (7)	−0.0095 (7)
C10	0.0620 (9)	0.0466 (8)	0.0553 (11)	0.0055 (7)	0.0014 (8)	−0.0167 (7)
O1	0.0907 (8)	0.0550 (7)	0.0685 (8)	0.0134 (6)	0.0062 (7)	0.0070 (6)
C4	0.0638 (9)	0.0637 (10)	0.0506 (10)	0.0091 (8)	0.0089 (8)	0.0151 (8)
C5	0.0774 (11)	0.0480 (9)	0.0693 (12)	0.0043 (8)	0.0140 (9)	0.0188 (9)
C6	0.0702 (10)	0.0384 (8)	0.0683 (12)	−0.0041 (7)	0.0080 (8)	0.0019 (8)

N2—C8	1.2684 (19)	N1—H1A	0.877 (18)
N2—C7	1.4131 (19)	N1—H1B	0.904 (18)
O2—N3	1.2238 (16)	C8—H8A	0.9300
O3—C1	1.2299 (15)	C14—C13	1.379 (2)
C9—C14	1.384 (2)	C14—H14A	0.9300
C9—C10	1.397 (2)	C13—H13A	0.9300
C9—C8	1.466 (2)	C3—C4	1.379 (2)
C2—C3	1.389 (2)	C3—H3A	0.9300
C2—C7	1.4053 (19)	C11—C10	1.365 (2)
C2—C1	1.5118 (19)	C11—H11A	0.9300
C1—N1	1.3241 (19)	C10—H10A	0.9300
N3—O1	1.2186 (16)	C4—C5	1.375 (2)
N3—C12	1.4645 (19)	C4—H4A	0.9300
C12—C13	1.372 (2)	C5—C6	1.375 (2)
C12—C11	1.377 (2)	C5—H5A	0.9300
C7—C6	1.392 (2)	C6—H6A	0.9300
C8—N2—C7	121.60 (12)	C13—C14—C9	120.91 (14)
C14—C9—C10	118.75 (14)	C13—C14—H14A	119.5
C14—C9—C8	120.25 (13)	C9—C14—H14A	119.5
C10—C9—C8	120.99 (13)	C12—C13—C14	118.60 (13)
C3—C2—C7	118.09 (13)	C12—C13—H13A	120.7
C3—C2—C1	116.21 (12)	C14—C13—H13A	120.7
C7—C2—C1	125.67 (13)	C4—C3—C2	121.88 (14)
O3—C1—N1	121.61 (13)	C4—C3—H3A	119.1
O3—C1—C2	119.27 (12)	C2—C3—H3A	119.1
N1—C1—C2	119.12 (12)	C10—C11—C12	118.97 (14)
O1—N3—O2	123.15 (14)	C10—C11—H11A	120.5
O1—N3—C12	118.47 (13)	C12—C11—H11A	120.5
O2—N3—C12	118.38 (12)	C11—C10—C9	120.79 (14)
C13—C12—C11	121.95 (14)	C11—C10—H10A	119.6
C13—C12—N3	119.32 (13)	C9—C10—H10A	119.6
C11—C12—N3	118.73 (13)	C5—C4—C3	119.60 (15)
C6—C7—C2	119.41 (14)	C5—C4—H4A	120.2
C6—C7—N2	121.19 (13)	C3—C4—H4A	120.2
C2—C7—N2	119.27 (12)	C4—C5—C6	119.97 (15)
C1—N1—H1A	119.1 (12)	C4—C5—H5A	120.0
C1—N1—H1B	117.8 (10)	C6—C5—H5A	120.0
H1A—N1—H1B	122.9 (15)	C5—C6—C7	121.04 (15)
N2—C8—C9	121.19 (13)	C5—C6—H6A	119.5
N2—C8—H8A	119.4	C7—C6—H6A	119.5
C9—C8—H8A	119.4
C3—C2—C1—O3	−7.15 (18)	C10—C9—C14—C13	1.0 (2)
C7—C2—C1—O3	170.60 (13)	C8—C9—C14—C13	179.76 (13)
C3—C2—C1—N1	173.09 (13)	C11—C12—C13—C14	1.0 (2)
C7—C2—C1—N1	−9.2 (2)	N3—C12—C13—C14	−178.97 (12)
O1—N3—C12—C13	177.42 (13)	C9—C14—C13—C12	−1.6 (2)
O2—N3—C12—C13	−2.95 (19)	C7—C2—C3—C4	0.5 (2)
O1—N3—C12—C11	−2.57 (19)	C1—C2—C3—C4	178.39 (13)
O2—N3—C12—C11	177.05 (13)	C13—C12—C11—C10	0.1 (2)
C3—C2—C7—C6	−0.8 (2)	N3—C12—C11—C10	−179.88 (13)
C1—C2—C7—C6	−178.46 (13)	C12—C11—C10—C9	−0.7 (2)
C3—C2—C7—N2	−176.60 (12)	C14—C9—C10—C11	0.2 (2)
C1—C2—C7—N2	5.7 (2)	C8—C9—C10—C11	−178.58 (14)
C8—N2—C7—C6	41.8 (2)	C2—C3—C4—C5	0.0 (2)
C8—N2—C7—C2	−142.45 (14)	C3—C4—C5—C6	−0.2 (2)
C7—N2—C8—C9	−178.08 (12)	C4—C5—C6—C7	−0.1 (3)
C14—C9—C8—N2	−178.12 (14)	C2—C7—C6—C5	0.6 (2)
C10—C9—C8—N2	0.6 (2)	N2—C7—C6—C5	176.34 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O2i	0.93	2.44	3.1903 (19)	138
N1—H1B···O3ii	0.904 (18)	2.059 (19)	2.9581 (17)	173.3 (15)
N1—H1A···N2	0.877 (18)	1.999 (18)	2.7027 (18)	136.4 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O2i	0.93	2.44	3.1903 (19)	138
N1—H1B⋯O3ii	0.904 (18)	2.059 (19)	2.9581 (17)	173.3 (15)
N1—H1A⋯N2	0.877 (18)	1.999 (18)	2.7027 (18)	136.4 (15)

Symmetry codes: (i) ; (ii) .