N-Benzyl-3-nitro-aniline.

The mol-ecule of the title compound, C(13)H(12)N(2)O(2), has a bent conformation with a torsion angle about the central C-N bond of 72.55 (19)°. In the crystal, the mol-ecules are connected via classical N-H⋯O and non-classical C-H⋯O hydrogen bonds into chains along [10[Formula: see text]]. The dihedral angle between the ring planes is 86.0 (6)°.

Related literature

For the synthesis of the title compound, see: Magyarfalvi (2008 ▶). For related structures, see: Betz et al. (2011 ▶); Iwasaki et al. (1988 ▶).

Experimental

Crystal data

C13H12N2O2

M = 228.25

Monoclinic,

a = 5.3359 (2) Å

b = 19.2285 (6) Å

c = 5.6017 (2) Å

β = 97.334 (3)°

V = 570.04 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.41 × 0.29 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

7072 measured reflections

1280 independent reflections

1093 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.01

1280 reflections

158 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data n class="Disease">reduction: CrysAlis RED; program used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), POV-RAY (Cason et al., 2002 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042632/rk2302sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042632/rk2302Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042632/rk2302Isup3.cml

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

C13H12N2O2	Z = 2
Mr = 228.25	F(000) = 240
Monoclinic, P21	Dx = 1.33 Mg m−3
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 5.3359 (2) Å	θ = 4.6–54.0°
b = 19.2285 (6) Å	µ = 0.09 mm−1
c = 5.6017 (2) Å	T = 295 K
β = 97.334 (3)°	Plate, yellow
V = 570.04 (3) Å3	0.41 × 0.29 × 0.23 mm

Oxford Diffraction Xcalibur CCD diffractometer	1093 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	Rint = 0.017
graphite	θmax = 27.0°, θmin = 3.8°
φ and ω scans	h = −6→6
7072 measured reflections	k = −24→24
1280 independent reflections	l = −7→7

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0615P)2] where P = (Fo2 + 2Fc2)/3
1280 reflections	(Δ/σ)max = 0.003
158 parameters	Δρmax = 0.14 e Å−3
3 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
H1	0.844 (5)	0.2074 (13)	0.076 (5)	0.063 (6)*
C3	0.2527 (3)	0.28407 (9)	0.4595 (3)	0.0412 (4)
C2	0.4146 (3)	0.23191 (9)	0.4090 (3)	0.0423 (4)
H2	0.4181	0.1896	0.4896	0.051*
C1	0.5737 (3)	0.24414 (9)	0.2335 (3)	0.0454 (4)
N2	0.0876 (3)	0.27154 (8)	0.6441 (3)	0.0489 (4)
C6	0.5584 (3)	0.30889 (10)	0.1187 (4)	0.0516 (4)
H6	0.6626	0.318	0.0013	0.062*
C4	0.2364 (4)	0.34794 (9)	0.3472 (4)	0.0528 (5)
H4	0.1244	0.382	0.3858	0.063*
N1	0.7446 (4)	0.19560 (9)	0.1759 (4)	0.0663 (5)
O2	−0.0522 (3)	0.31801 (9)	0.6928 (3)	0.0763 (5)
O1	0.0942 (3)	0.21462 (8)	0.7433 (3)	0.0645 (4)
C5	0.3954 (4)	0.35886 (10)	0.1740 (4)	0.0579 (5)
H5	0.3905	0.4013	0.0939	0.069*
C8	0.5655 (3)	0.07735 (9)	0.2164 (3)	0.0496 (4)
C7	0.7768 (4)	0.12849 (11)	0.2881 (5)	0.0616 (5)
H7A	0.7937	0.1347	0.4612	0.074*
H7B	0.9335	0.1085	0.2492	0.074*
C11	0.1852 (4)	−0.01992 (12)	0.0930 (5)	0.0705 (6)
H11	0.0576	−0.0523	0.0518	0.085*
C13	0.4114 (4)	0.08153 (12)	−0.0021 (3)	0.0666 (6)
H13	0.4348	0.1172	−0.1093	0.08*
C10	0.3354 (5)	−0.02457 (12)	0.3060 (5)	0.0739 (6)
H10	0.3118	−0.0606	0.4115	0.089*
C9	0.5222 (4)	0.02354 (12)	0.3673 (4)	0.0651 (5)
H9	0.6224	0.0197	0.5152	0.078*
C12	0.2233 (5)	0.03297 (16)	−0.0607 (4)	0.0764 (6)
H12	0.1207	0.0363	−0.2075	0.092*

	U11	U22	U33	U12	U13	U23
C3	0.0386 (7)	0.0460 (9)	0.0405 (8)	−0.0039 (7)	0.0116 (6)	−0.0028 (6)
C2	0.0431 (8)	0.0405 (8)	0.0456 (9)	−0.0033 (7)	0.0142 (7)	0.0021 (7)
C1	0.0417 (8)	0.0458 (9)	0.0515 (10)	−0.0066 (7)	0.0164 (7)	−0.0044 (7)
N2	0.0472 (8)	0.0573 (9)	0.0444 (8)	−0.0030 (7)	0.0150 (6)	−0.0023 (7)
C6	0.0508 (10)	0.0569 (10)	0.0510 (10)	−0.0126 (9)	0.0211 (8)	0.0032 (8)
C4	0.0524 (10)	0.0441 (10)	0.0643 (12)	0.0042 (8)	0.0163 (9)	0.0017 (8)
N1	0.0602 (10)	0.0540 (10)	0.0943 (13)	0.0002 (8)	0.0470 (10)	−0.0012 (9)
O2	0.0773 (10)	0.0795 (11)	0.0811 (11)	0.0173 (9)	0.0447 (9)	−0.0031 (8)
O1	0.0718 (9)	0.0671 (9)	0.0601 (8)	−0.0025 (7)	0.0301 (7)	0.0108 (7)
C5	0.0603 (11)	0.0484 (11)	0.0671 (12)	−0.0028 (9)	0.0164 (10)	0.0147 (8)
C8	0.0481 (9)	0.0457 (10)	0.0577 (10)	0.0089 (8)	0.0171 (8)	−0.0069 (7)
C7	0.0468 (10)	0.0517 (10)	0.0892 (16)	0.0051 (8)	0.0201 (10)	−0.0067 (10)
C11	0.0620 (12)	0.0589 (12)	0.0913 (17)	−0.0032 (10)	0.0128 (12)	−0.0219 (9)
C13	0.0778 (14)	0.0645 (12)	0.0581 (13)	0.0059 (11)	0.0112 (11)	0.0051 (9)
C10	0.0851 (16)	0.0572 (12)	0.0803 (16)	−0.0117 (12)	0.0134 (13)	0.0030 (11)
C9	0.0722 (12)	0.0600 (12)	0.0617 (12)	−0.0029 (11)	0.0030 (10)	0.0041 (10)
C12	0.0778 (14)	0.0816 (14)	0.0653 (13)	0.0054 (13)	−0.0079 (11)	−0.0111 (10)

C3—C2	1.376 (2)	C5—H5	0.93
C3—C4	1.378 (2)	C8—C9	1.374 (3)
C3—N2	1.461 (2)	C8—C13	1.3868 (17)
C2—C1	1.398 (2)	C8—C7	1.511 (3)
C2—H2	0.93	C7—H7A	0.97
C1—N1	1.372 (2)	C7—H7B	0.97
C1—C6	1.399 (3)	C11—C10	1.353 (4)
N2—O2	1.217 (2)	C11—C12	1.364 (4)
N2—O1	1.226 (2)	C11—H11	0.93
C6—C5	1.358 (3)	C13—C12	1.379 (4)
C6—H6	0.93	C13—H13	0.93
C4—C5	1.384 (3)	C10—C9	1.371 (3)
C4—H4	0.93	C10—H10	0.93
N1—C7	1.436 (3)	C9—H9	0.93
N1—H1	0.85 (3)	C12—H12	0.93
C2—C3—C4	124.08 (15)	C9—C8—C13	117.32 (18)
C2—C3—N2	118.44 (14)	C9—C8—C7	120.31 (17)
C4—C3—N2	117.48 (15)	C13—C8—C7	122.36 (19)
C3—C2—C1	118.37 (15)	N1—C7—C8	115.13 (19)
C3—C2—H2	120.8	N1—C7—H7A	108.5
C1—C2—H2	120.8	C8—C7—H7A	108.5
N1—C1—C2	122.14 (17)	N1—C7—H7B	108.5
N1—C1—C6	119.94 (16)	C8—C7—H7B	108.5
C2—C1—C6	117.90 (16)	H7A—C7—H7B	107.5
O2—N2—O1	122.47 (15)	C10—C11—C12	119.1 (2)
O2—N2—C3	118.66 (16)	C10—C11—H11	120.4
O1—N2—C3	118.87 (14)	C12—C11—H11	120.4
C5—C6—C1	121.74 (16)	C12—C13—C8	120.2 (2)
C5—C6—H6	119.1	C12—C13—H13	119.9
C1—C6—H6	119.1	C8—C13—H13	119.9
C3—C4—C5	116.54 (16)	C11—C10—C9	120.4 (2)
C3—C4—H4	121.7	C11—C10—H10	119.8
C5—C4—H4	121.7	C9—C10—H10	119.8
C1—N1—C7	123.70 (18)	C10—C9—C8	121.9 (2)
C1—N1—H1	117.6 (17)	C10—C9—H9	119.1
C7—N1—H1	118.6 (17)	C8—C9—H9	119.1
C6—C5—C4	121.36 (17)	C11—C12—C13	121.1 (2)
C6—C5—H5	119.3	C11—C12—H12	119.4
C4—C5—H5	119.3	C13—C12—H12	119.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.84 (2)	2.44 (2)	3.263 (2)	166 (2)
C6—H6···O2i	0.93	2.45	3.364 (2)	169
C13—H13···O1ii	0.93	2.67	3.293 (2)	125
C7—H7A···O1iii	0.97	2.61	3.318 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.84 (2)	2.44 (2)	3.263 (2)	166 (2)
C6—H6⋯O2i	0.93	2.45	3.364 (2)	169
C13—H13⋯O1ii	0.93	2.67	3.293 (2)	125
C7—H7A⋯O1iii	0.97	2.61	3.318 (2)	130

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