4-Methyl-benzyl 4-amino-benzoate.

The dihedral angle between the two benzene rings in the title compound, C(15)H(15)NO(2), is 65.28 (12)°. The crystal structure is stabilized by N-H⋯N and N-H⋯O hydrogen bonds, leading to the formation of supra-molecular chains along the a-axis direction.

Related literature

For the reduction of aryl-nitro compounds, see: Tafesh & Weiguny (1996 ▶); Vass et al. (2001 ▶); Entwistle et al. (1977 ▶); Bavin (1958 ▶); Yuste et al. (1982 ▶); Idrees et al. (2009 ▶). For the uses of amines, see: Kumarraja & Pitchumani (2004 ▶).

Experimental

Crystal data

C15H15NO2

M = 241.28

Monoclinic,

a = 8.2097 (12) Å

b = 5.5344 (5) Å

c = 14.293 (2) Å

β = 98.531 (12)°

V = 642.24 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.27 × 0.13 × 0.13 mm

Data collection

Stoe IPDSII two-circle diffractometer

4021 measured reflections

1322 independent reflections

960 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.094

S = 0.91

1322 reflections

173 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007075/tk2629sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007075/tk2629Isup2.hkl

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

C15H15NO2	F(000) = 256
Mr = 241.28	Dx = 1.248 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2492 reflections
a = 8.2097 (12) Å	θ = 4.0–25.9°
b = 5.5344 (5) Å	µ = 0.08 mm−1
c = 14.293 (2) Å	T = 173 K
β = 98.531 (12)°	Prism, colourless
V = 642.24 (14) Å3	0.27 × 0.13 × 0.13 mm
Z = 2

Stoe IPDSII two-circle diffractometer	960 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.093
graphite	θmax = 25.7°, θmin = 3.5°
ω scans	h = −9→9
4021 measured reflections	k = −6→5
1322 independent reflections	l = −17→17

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0405P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max = 0.028
1322 reflections	Δρmax = 0.14 e Å−3
173 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.077 (11)

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
N1	0.0100 (4)	0.0360 (6)	0.9396 (2)	0.0442 (8)
H1A	−0.086 (5)	0.090 (9)	0.911 (3)	0.057 (12)*
H1B	0.007 (7)	−0.130 (11)	0.958 (3)	0.090 (17)*
O1	0.5634 (3)	0.6085 (5)	0.77036 (17)	0.0454 (6)
O2	0.7240 (3)	0.3098 (5)	0.83952 (16)	0.0468 (7)
C1	0.7064 (5)	0.7251 (7)	0.7398 (3)	0.0475 (9)
H1C	0.8064	0.6833	0.7845	0.057*
H1D	0.6922	0.9027	0.7412	0.057*
C2	0.5874 (4)	0.4043 (6)	0.8206 (2)	0.0347 (8)
C11	0.7290 (4)	0.6485 (6)	0.6420 (2)	0.0383 (8)
C12	0.8155 (4)	0.4400 (6)	0.6259 (2)	0.0414 (9)
H12	0.8593	0.3410	0.6779	0.050*
C13	0.8388 (4)	0.3743 (6)	0.5354 (2)	0.0405 (9)
H13	0.8994	0.2321	0.5265	0.049*
C14	0.7755 (4)	0.5117 (6)	0.4576 (2)	0.0405 (8)
C15	0.6888 (5)	0.7204 (7)	0.4742 (3)	0.0511 (11)
H15	0.6446	0.8195	0.4224	0.061*
C16	0.6659 (4)	0.7853 (7)	0.5643 (3)	0.0464 (9)
H16	0.6053	0.9276	0.5733	0.056*
C17	0.7999 (6)	0.4368 (9)	0.3599 (3)	0.0601 (12)
H17A	0.6988	0.3612	0.3278	0.090*
H17B	0.8909	0.3210	0.3639	0.090*
H17C	0.8258	0.5792	0.3241	0.090*
C21	0.4371 (4)	0.3093 (6)	0.8495 (2)	0.0337 (8)
C22	0.4413 (4)	0.0941 (6)	0.9016 (2)	0.0345 (8)
H22	0.5425	0.0099	0.9172	0.041*
C23	0.3008 (4)	0.0031 (6)	0.9306 (2)	0.0376 (8)
H23	0.3064	−0.1430	0.9659	0.045*
C24	0.1503 (4)	0.1226 (6)	0.90885 (19)	0.0321 (7)
C25	0.1451 (4)	0.3382 (7)	0.8578 (2)	0.0373 (8)
H25	0.0437	0.4225	0.8429	0.045*
C26	0.2854 (4)	0.4302 (6)	0.82882 (19)	0.0352 (8)
H26	0.2796	0.5774	0.7943	0.042*

	U11	U22	U33	U12	U13	U23
N1	0.0384 (18)	0.047 (2)	0.0480 (17)	−0.0004 (15)	0.0081 (14)	0.0099 (15)
O1	0.0416 (14)	0.0390 (13)	0.0604 (14)	0.0023 (12)	0.0232 (11)	0.0028 (12)
O2	0.0303 (13)	0.0573 (16)	0.0533 (14)	0.0020 (13)	0.0077 (11)	−0.0018 (13)
C1	0.048 (2)	0.036 (2)	0.064 (2)	−0.0084 (18)	0.0270 (18)	−0.0041 (17)
C2	0.0344 (19)	0.0332 (18)	0.0375 (16)	0.0003 (16)	0.0084 (14)	−0.0069 (15)
C11	0.0316 (18)	0.0346 (19)	0.0508 (18)	−0.0047 (15)	0.0133 (14)	−0.0020 (15)
C12	0.042 (2)	0.040 (2)	0.0413 (16)	0.0086 (17)	0.0056 (14)	0.0014 (15)
C13	0.040 (2)	0.0333 (19)	0.0489 (19)	0.0037 (15)	0.0086 (15)	−0.0030 (15)
C14	0.037 (2)	0.038 (2)	0.0455 (17)	−0.0061 (17)	0.0059 (15)	−0.0006 (16)
C15	0.044 (2)	0.047 (2)	0.060 (2)	−0.0007 (19)	0.0001 (18)	0.0148 (18)
C16	0.040 (2)	0.0305 (18)	0.073 (2)	0.0047 (17)	0.0207 (17)	0.0053 (18)
C17	0.067 (3)	0.069 (3)	0.0439 (19)	−0.011 (2)	0.0063 (18)	−0.004 (2)
C21	0.0356 (18)	0.0357 (18)	0.0300 (14)	0.0023 (16)	0.0059 (13)	−0.0047 (14)
C22	0.0321 (18)	0.0365 (18)	0.0349 (15)	0.0051 (16)	0.0054 (13)	−0.0051 (14)
C23	0.043 (2)	0.0371 (18)	0.0314 (16)	0.0012 (17)	0.0011 (14)	−0.0023 (13)
C24	0.0346 (18)	0.0328 (17)	0.0295 (14)	−0.0026 (16)	0.0069 (13)	−0.0048 (14)
C25	0.0319 (17)	0.045 (2)	0.0349 (16)	0.0060 (17)	0.0061 (13)	0.0029 (15)
C26	0.039 (2)	0.0351 (18)	0.0328 (15)	0.0049 (16)	0.0090 (14)	0.0021 (14)

N1—C24	1.378 (5)	C14—C17	1.499 (5)
N1—H1A	0.88 (4)	C15—C16	1.377 (5)
N1—H1B	0.96 (6)	C15—H15	0.9500
O1—C2	1.338 (4)	C16—H16	0.9500
O1—C1	1.462 (4)	C17—H17A	0.9800
O2—C2	1.230 (4)	C17—H17B	0.9800
C1—C11	1.499 (5)	C17—H17C	0.9800
C1—H1C	0.9900	C21—C22	1.402 (5)
C1—H1D	0.9900	C21—C26	1.406 (4)
C2—C21	1.457 (5)	C22—C23	1.378 (5)
C11—C16	1.379 (5)	C22—H22	0.9500
C11—C12	1.392 (5)	C23—C24	1.395 (5)
C12—C13	1.384 (5)	C23—H23	0.9500
C12—H12	0.9500	C24—C25	1.396 (5)
C13—C14	1.383 (5)	C25—C26	1.378 (5)
C13—H13	0.9500	C25—H25	0.9500
C14—C15	1.395 (5)	C26—H26	0.9500
C24—N1—H1A	118 (3)	C15—C16—C11	121.5 (3)
C24—N1—H1B	119 (3)	C15—C16—H16	119.3
H1A—N1—H1B	113 (5)	C11—C16—H16	119.3
C2—O1—C1	118.2 (3)	C14—C17—H17A	109.5
O1—C1—C11	111.7 (3)	C14—C17—H17B	109.5
O1—C1—H1C	109.3	H17A—C17—H17B	109.5
C11—C1—H1C	109.3	C14—C17—H17C	109.5
O1—C1—H1D	109.3	H17A—C17—H17C	109.5
C11—C1—H1D	109.3	H17B—C17—H17C	109.5
H1C—C1—H1D	107.9	C22—C21—C26	117.9 (3)
O2—C2—O1	122.3 (3)	C22—C21—C2	120.1 (3)
O2—C2—C21	124.5 (3)	C26—C21—C2	122.0 (3)
O1—C2—C21	113.2 (3)	C23—C22—C21	121.0 (3)
C16—C11—C12	117.5 (3)	C23—C22—H22	119.5
C16—C11—C1	120.8 (3)	C21—C22—H22	119.5
C12—C11—C1	121.7 (3)	C22—C23—C24	120.8 (3)
C13—C12—C11	121.1 (3)	C22—C23—H23	119.6
C13—C12—H12	119.5	C24—C23—H23	119.6
C11—C12—H12	119.5	N1—C24—C23	121.2 (3)
C14—C13—C12	121.3 (3)	N1—C24—C25	120.1 (3)
C14—C13—H13	119.4	C23—C24—C25	118.6 (3)
C12—C13—H13	119.4	C26—C25—C24	120.7 (3)
C13—C14—C15	117.3 (3)	C26—C25—H25	119.6
C13—C14—C17	120.7 (3)	C24—C25—H25	119.6
C15—C14—C17	122.0 (3)	C25—C26—C21	121.0 (3)
C16—C15—C14	121.3 (3)	C25—C26—H26	119.5
C16—C15—H15	119.4	C21—C26—H26	119.5
C14—C15—H15	119.4
C2—O1—C1—C11	94.1 (4)	O2—C2—C21—C22	−0.9 (4)
C1—O1—C2—O2	−1.9 (5)	O1—C2—C21—C22	179.1 (3)
C1—O1—C2—C21	178.1 (3)	O2—C2—C21—C26	177.6 (3)
O1—C1—C11—C16	95.1 (4)	O1—C2—C21—C26	−2.4 (4)
O1—C1—C11—C12	−85.7 (4)	C26—C21—C22—C23	0.7 (4)
C16—C11—C12—C13	0.8 (5)	C2—C21—C22—C23	179.2 (3)
C1—C11—C12—C13	−178.5 (4)	C21—C22—C23—C24	0.0 (4)
C11—C12—C13—C14	−0.8 (5)	C22—C23—C24—N1	−178.3 (3)
C12—C13—C14—C15	0.7 (5)	C22—C23—C24—C25	−0.7 (4)
C12—C13—C14—C17	−179.2 (4)	N1—C24—C25—C26	178.2 (3)
C13—C14—C15—C16	−0.6 (5)	C23—C24—C25—C26	0.6 (4)
C17—C14—C15—C16	179.3 (4)	C24—C25—C26—C21	0.2 (4)
C14—C15—C16—C11	0.7 (6)	C22—C21—C26—C25	−0.8 (4)
C12—C11—C16—C15	−0.7 (5)	C2—C21—C26—C25	−179.3 (3)
C1—C11—C16—C15	178.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.88 (4)	2.12 (5)	2.977 (4)	164 (4)
N1—H1B···N1ii	0.96 (6)	2.37 (6)	3.278 (3)	158 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.88 (4)	2.12 (5)	2.977 (4)	164 (4)
N1—H1B⋯N1ii	0.96 (6)	2.37 (6)	3.278 (3)	158 (4)

Symmetry codes: (i) ; (ii) .