4-(p-Tolyl-amino)-benzaldehyde.

In the title compound, C(14)H(13)NO, the dihedral angle between the aromatic rings is 66.08 (9)°. Chains are formed along the b axis through inter-molecular N-H⋯O hydrogen bonds. The crystal structure is further stabilized by C-H⋯π inter-actions.

Related literature

For applications and bioactivity of diaryl­amines, see: Abou-Seri (2010 ▶); Kostrab et al. (2008 ▶).

Experimental

Crystal data

C14H13NO

M = 211.25

Orthorhombic,

a = 5.8356 (12) Å

b = 8.2581 (18) Å

c = 24.137 (5) Å

V = 1163.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART area-detector diffractometer

6780 measured reflections

1555 independent reflections

1414 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 1.07

1555 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040389/zl2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040389/zl2311Isup2.hkl

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

C14H13NO	Dx = 1.206 Mg m−3
Mr = 211.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 3865 reflections
a = 5.8356 (12) Å	θ = 2.6–27.0°
b = 8.2581 (18) Å	µ = 0.08 mm−1
c = 24.137 (5) Å	T = 298 K
V = 1163.2 (4) Å3	Block, brown
Z = 4	0.20 × 0.20 × 0.10 mm
F(000) = 448

Bruker SMART area-detector diffractometer	1414 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 27.4°, θmin = 2.6°
phi and ω scans	h = −7→7
6780 measured reflections	k = −10→7
1555 independent reflections	l = −31→24

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0662P)2 + 0.0847P] where P = (Fo2 + 2Fc2)/3
1555 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.16 e Å−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
C13	1.3763 (3)	0.6409 (2)	0.06501 (7)	0.0509 (4)
H13	1.4615	0.5491	0.0564	0.061*
C11	1.3240 (3)	0.9306 (2)	0.05882 (6)	0.0506 (4)
C8	1.1747 (3)	0.6263 (2)	0.09648 (6)	0.0490 (4)
C12	1.4480 (3)	0.7908 (2)	0.04698 (6)	0.0502 (4)
H12	1.5823	0.7988	0.0264	0.060*
C5	0.9454 (3)	0.4459 (2)	0.15636 (7)	0.0537 (4)
C10	1.1209 (3)	0.9158 (2)	0.08968 (7)	0.0536 (4)
H10	1.0348	1.0077	0.0976	0.064*
N1	1.1016 (3)	0.4765 (2)	0.11257 (7)	0.0638 (5)
C9	1.0479 (3)	0.7677 (2)	0.10832 (7)	0.0530 (4)
H9	0.9137	0.7603	0.1289	0.064*
C3	0.8304 (3)	0.4783 (2)	0.25130 (7)	0.0588 (5)
H3	0.8561	0.5239	0.2860	0.071*
C2	0.6412 (3)	0.3791 (2)	0.24364 (8)	0.0568 (4)
C14	1.4066 (4)	1.0868 (2)	0.03930 (8)	0.0650 (5)
C6	0.7577 (4)	0.3455 (3)	0.14822 (9)	0.0667 (5)
H6	0.7321	0.2995	0.1136	0.080*
C7	0.6087 (4)	0.3136 (3)	0.19139 (9)	0.0682 (5)
H7	0.4834	0.2464	0.1852	0.082*
C4	0.9812 (3)	0.5110 (2)	0.20869 (8)	0.0587 (5)
H4	1.1076	0.5770	0.2151	0.070*
C1	0.4755 (4)	0.3446 (3)	0.29038 (9)	0.0733 (6)
H1A	0.5256	0.3995	0.3233	0.110*
H1B	0.4702	0.2301	0.2972	0.110*
H1C	0.3255	0.3823	0.2803	0.110*
O2	1.3205 (4)	1.21695 (17)	0.04864 (7)	0.0910 (6)
H1	1.162 (5)	0.393 (3)	0.0987 (10)	0.076 (7)*
H14	1.551 (5)	1.074 (3)	0.0161 (11)	0.087 (7)*

	U11	U22	U33	U12	U13	U23
C13	0.0529 (9)	0.0508 (9)	0.0490 (8)	0.0106 (8)	0.0053 (7)	−0.0020 (7)
C11	0.0570 (9)	0.0502 (9)	0.0446 (7)	0.0004 (8)	0.0003 (7)	−0.0041 (7)
C8	0.0523 (8)	0.0529 (8)	0.0419 (7)	0.0040 (8)	0.0004 (7)	0.0004 (7)
C12	0.0486 (8)	0.0565 (9)	0.0454 (8)	0.0030 (8)	0.0047 (7)	−0.0030 (7)
C5	0.0563 (9)	0.0489 (8)	0.0558 (9)	0.0009 (9)	0.0032 (8)	0.0065 (7)
C10	0.0582 (10)	0.0513 (9)	0.0514 (8)	0.0125 (8)	0.0035 (8)	−0.0045 (7)
N1	0.0748 (11)	0.0499 (8)	0.0666 (10)	0.0029 (9)	0.0189 (9)	0.0005 (7)
C9	0.0491 (8)	0.0585 (9)	0.0513 (8)	0.0074 (8)	0.0073 (8)	−0.0002 (7)
C3	0.0582 (9)	0.0669 (11)	0.0514 (9)	−0.0040 (9)	−0.0042 (8)	0.0070 (8)
C2	0.0509 (9)	0.0592 (10)	0.0603 (10)	0.0016 (9)	−0.0016 (8)	0.0133 (8)
C14	0.0802 (14)	0.0515 (10)	0.0634 (10)	−0.0061 (11)	0.0099 (11)	−0.0073 (8)
C6	0.0773 (13)	0.0638 (11)	0.0591 (10)	−0.0120 (11)	−0.0060 (10)	−0.0020 (9)
C7	0.0612 (11)	0.0691 (12)	0.0744 (11)	−0.0182 (11)	−0.0038 (10)	0.0073 (10)
C4	0.0516 (9)	0.0642 (10)	0.0602 (10)	−0.0113 (9)	−0.0036 (8)	0.0056 (8)
C1	0.0611 (11)	0.0859 (14)	0.0727 (12)	−0.0038 (12)	0.0070 (10)	0.0197 (11)
O2	0.1203 (14)	0.0497 (8)	0.1029 (12)	0.0005 (10)	0.0241 (11)	−0.0093 (8)

C13—C12	1.377 (3)	C9—H9	0.9300
C13—C8	1.406 (3)	C3—C4	1.380 (3)
C13—H13	0.9300	C3—C2	1.387 (3)
C11—C12	1.392 (2)	C3—H3	0.9300
C11—C10	1.405 (3)	C2—C7	1.385 (3)
C11—C14	1.455 (3)	C2—C1	1.513 (3)
C8—N1	1.365 (2)	C14—O2	1.208 (3)
C8—C9	1.411 (2)	C14—H14	1.02 (3)
C12—H12	0.9300	C6—C7	1.383 (3)
C5—C6	1.388 (3)	C6—H6	0.9300
C5—C4	1.388 (3)	C7—H7	0.9300
C5—N1	1.419 (2)	C4—H4	0.9300
C10—C9	1.371 (2)	C1—H1A	0.9600
C10—H10	0.9300	C1—H1B	0.9600
N1—H1	0.84 (2)	C1—H1C	0.9600
C12—C13—C8	120.13 (16)	C4—C3—C2	121.58 (17)
C12—C13—H13	119.9	C4—C3—H3	119.2
C8—C13—H13	119.9	C2—C3—H3	119.2
C12—C11—C10	118.36 (16)	C7—C2—C3	117.45 (17)
C12—C11—C14	119.75 (17)	C7—C2—C1	121.18 (18)
C10—C11—C14	121.89 (17)	C3—C2—C1	121.36 (18)
N1—C8—C13	119.53 (16)	O2—C14—C11	126.2 (2)
N1—C8—C9	121.91 (16)	O2—C14—H14	122.7 (14)
C13—C8—C9	118.50 (16)	C11—C14—H14	111.1 (14)
C13—C12—C11	121.52 (16)	C7—C6—C5	120.24 (19)
C13—C12—H12	119.2	C7—C6—H6	119.9
C11—C12—H12	119.2	C5—C6—H6	119.9
C6—C5—C4	118.60 (16)	C6—C7—C2	121.70 (19)
C6—C5—N1	120.55 (17)	C6—C7—H7	119.1
C4—C5—N1	120.81 (17)	C2—C7—H7	119.1
C9—C10—C11	120.89 (16)	C3—C4—C5	120.41 (17)
C9—C10—H10	119.6	C3—C4—H4	119.8
C11—C10—H10	119.6	C5—C4—H4	119.8
C8—N1—C5	125.06 (16)	C2—C1—H1A	109.5
C8—N1—H1	119.7 (17)	C2—C1—H1B	109.5
C5—N1—H1	114.8 (17)	H1A—C1—H1B	109.5
C10—C9—C8	120.59 (16)	C2—C1—H1C	109.5
C10—C9—H9	119.7	H1A—C1—H1C	109.5
C8—C9—H9	119.7	H1B—C1—H1C	109.5

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.84 (3)	2.11 (3)	2.934 (2)	167 (2)
C1—H1A···Cg1ii	0.96	2.91	3.613 (2)	131
C12—H12···Cg1iii	0.93	2.77	3.527 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.84 (3)	2.11 (3)	2.934 (2)	167 (2)
C1—H1A⋯Cg1ii	0.96	2.91	3.613 (2)	131
C12—H12⋯Cg1iii	0.93	2.77	3.527 (2)	140

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