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

In the title compound, C(14)H(13)NO, the dihedral angle between the aromatic rings is 49.64 (18)°. The crystal structure is stabilized by N-H⋯O, C-H⋯O and C-H⋯π hydrogen bonds.

Related literature

For applications and bioactivity of diaryl­amines, see: Ohta et al. (2008 ▶); Li et al. (2008 ▶).

Experimental

Crystal data

C14H13NO

M = 211.25

Orthorhombic,

a = 14.193 (10) Å

b = 10.699 (10) Å

c = 7.677 (6) Å

V = 1165.9 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 273 K

0.20 × 0.15 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

6127 measured reflections

1397 independent reflections

1140 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.157

S = 1.06

1397 reflections

153 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040626/si2297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040626/si2297Isup2.hkl

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

C14H13NO	Dx = 1.204 Mg m−3
Mr = 211.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2572 reflections
a = 14.193 (10) Å	θ = 2.4–26.6°
b = 10.699 (10) Å	µ = 0.08 mm−1
c = 7.677 (6) Å	T = 273 K
V = 1165.9 (16) Å3	Plate, brown
Z = 4	0.20 × 0.15 × 0.05 mm
F(000) = 448

Bruker SMART CCD area-detector diffractometer	1140 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 27.4°, θmin = 1.9°
phi and ω scans	h = −18→14
6127 measured reflections	k = −13→13
1397 independent reflections	l = −6→9

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.1027P)2 + 0.0736P] where P = (Fo2 + 2Fc2)/3
1397 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.21 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
C6	1.07328 (19)	0.7362 (2)	0.3779 (5)	0.0546 (7)
H6	1.0775	0.8092	0.4432	0.066*
C5	0.99125 (16)	0.7114 (2)	0.2798 (4)	0.0476 (6)
N1	0.91447 (16)	0.7907 (2)	0.2760 (4)	0.0567 (7)
C8	0.91320 (18)	0.9212 (2)	0.3158 (4)	0.0496 (7)
C4	0.98692 (19)	0.5966 (2)	0.1871 (5)	0.0534 (7)
H4	0.9324	0.5758	0.1265	0.064*
C3	1.0628 (2)	0.5154 (2)	0.1858 (5)	0.0548 (7)
H3	1.0591	0.4418	0.1217	0.066*
C2	1.14506 (19)	0.5424 (2)	0.2797 (5)	0.0531 (7)
C13	0.83034 (19)	0.9730 (2)	0.3886 (5)	0.0557 (7)
O1	1.23816 (19)	0.36802 (18)	0.1876 (6)	0.0897 (10)
C1	1.2296 (2)	0.4612 (3)	0.2747 (6)	0.0660 (9)
C7	1.1475 (2)	0.6520 (2)	0.3770 (5)	0.0581 (8)
H7	1.2006	0.6694	0.4437	0.070*
C9	0.9897 (2)	0.9981 (3)	0.2718 (5)	0.0577 (7)
H9	1.0431	0.9638	0.2204	0.069*
C14	0.7450 (3)	0.8922 (3)	0.4262 (8)	0.0821 (11)
H14A	0.7589	0.8069	0.3968	0.123*
H14B	0.6926	0.9208	0.3580	0.123*
H14C	0.7295	0.8976	0.5477	0.123*
C12	0.8298 (3)	1.1013 (3)	0.4195 (6)	0.0742 (10)
H12	0.7765	1.1371	0.4693	0.089*
C10	0.9854 (2)	1.1256 (3)	0.3053 (7)	0.0728 (11)
H10	1.0365	1.1764	0.2781	0.087*
C11	0.9052 (3)	1.1773 (3)	0.3790 (7)	0.0814 (12)
H11	0.9023	1.2627	0.4011	0.098*
H1A	1.286 (2)	0.483 (3)	0.339 (5)	0.063 (9)*
H1	0.869 (3)	0.755 (3)	0.244 (5)	0.070 (11)*

	U11	U22	U33	U12	U13	U23
C6	0.0502 (14)	0.0407 (13)	0.0730 (19)	0.0008 (10)	−0.0053 (14)	−0.0097 (14)
C5	0.0395 (11)	0.0388 (12)	0.0645 (17)	−0.0005 (9)	0.0042 (12)	−0.0001 (14)
N1	0.0375 (10)	0.0445 (11)	0.0881 (19)	−0.0002 (9)	−0.0052 (12)	−0.0093 (14)
C8	0.0417 (12)	0.0427 (13)	0.0645 (18)	0.0050 (10)	−0.0062 (12)	−0.0031 (13)
C4	0.0441 (12)	0.0446 (12)	0.0716 (19)	−0.0062 (10)	−0.0046 (14)	−0.0073 (15)
C3	0.0586 (15)	0.0355 (11)	0.0704 (18)	−0.0036 (11)	0.0043 (15)	−0.0069 (15)
C2	0.0487 (13)	0.0375 (11)	0.0730 (19)	0.0034 (10)	0.0040 (14)	0.0039 (14)
C13	0.0469 (14)	0.0554 (15)	0.0646 (18)	0.0144 (11)	−0.0045 (14)	0.0001 (15)
O1	0.0794 (16)	0.0617 (12)	0.128 (3)	0.0276 (12)	−0.0038 (18)	−0.0164 (18)
C1	0.0559 (17)	0.0496 (15)	0.093 (3)	0.0101 (13)	−0.0029 (18)	0.0025 (19)
C7	0.0478 (14)	0.0446 (13)	0.082 (2)	0.0010 (11)	−0.0105 (15)	−0.0024 (15)
C9	0.0470 (13)	0.0486 (13)	0.077 (2)	0.0005 (10)	−0.0054 (15)	0.0012 (16)
C14	0.0541 (16)	0.090 (2)	0.102 (3)	0.0158 (18)	0.0239 (18)	0.008 (2)
C12	0.0644 (19)	0.0643 (18)	0.094 (3)	0.0275 (15)	−0.0133 (19)	−0.015 (2)
C10	0.0631 (17)	0.0484 (15)	0.107 (3)	−0.0040 (13)	−0.022 (2)	0.006 (2)
C11	0.083 (2)	0.0442 (15)	0.117 (3)	0.0170 (17)	−0.035 (2)	−0.010 (2)

C6—C7	1.386 (4)	C13—C12	1.393 (4)
C6—C5	1.412 (4)	C13—C14	1.516 (5)
C6—H6	0.9300	O1—C1	1.207 (5)
C5—N1	1.381 (3)	C1—H1A	0.97 (4)
C5—C4	1.421 (4)	C7—H7	0.9300
N1—C8	1.429 (4)	C9—C10	1.390 (5)
N1—H1	0.80 (4)	C9—H9	0.9300
C8—C9	1.403 (4)	C14—H14A	0.9600
C8—C13	1.415 (4)	C14—H14B	0.9600
C4—C3	1.383 (4)	C14—H14C	0.9600
C4—H4	0.9300	C12—C11	1.381 (6)
C3—C2	1.403 (4)	C12—H12	0.9300
C3—H3	0.9300	C10—C11	1.386 (6)
C2—C7	1.391 (4)	C10—H10	0.9300
C2—C1	1.481 (4)	C11—H11	0.9300
C7—C6—C5	120.1 (2)	O1—C1—C2	125.5 (4)
C7—C6—H6	119.9	O1—C1—H1A	113.4 (19)
C5—C6—H6	119.9	C2—C1—H1A	121.0 (19)
N1—C5—C6	123.1 (2)	C6—C7—C2	122.2 (3)
N1—C5—C4	119.1 (2)	C6—C7—H7	118.9
C6—C5—C4	117.7 (2)	C2—C7—H7	118.9
C5—N1—C8	127.2 (2)	C10—C9—C8	119.8 (3)
C5—N1—H1	111 (2)	C10—C9—H9	120.1
C8—N1—H1	122 (2)	C8—C9—H9	120.1
C9—C8—C13	120.6 (2)	C13—C14—H14A	109.5
C9—C8—N1	120.7 (2)	C13—C14—H14B	109.5
C13—C8—N1	118.5 (2)	H14A—C14—H14B	109.5
C3—C4—C5	120.8 (3)	C13—C14—H14C	109.5
C3—C4—H4	119.6	H14A—C14—H14C	109.5
C5—C4—H4	119.6	H14B—C14—H14C	109.5
C4—C3—C2	121.0 (3)	C11—C12—C13	122.5 (3)
C4—C3—H3	119.5	C11—C12—H12	118.7
C2—C3—H3	119.5	C13—C12—H12	118.7
C7—C2—C3	118.0 (2)	C11—C10—C9	120.2 (3)
C7—C2—C1	119.3 (3)	C11—C10—H10	119.9
C3—C2—C1	122.7 (3)	C9—C10—H10	119.9
C12—C13—C8	117.3 (3)	C12—C11—C10	119.6 (3)
C12—C13—C14	121.7 (3)	C12—C11—H11	120.2
C8—C13—C14	121.1 (2)	C10—C11—H11	120.2

Cg1 is the centroid of the C8–C13 tolyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···N1	0.96	2.40	2.880 (6)	110
N1—H1···O1i	0.79 (4)	2.32 (4)	3.099 (5)	171 (3)
C14—H14A···O1i	0.96	2.48	3.334 (6)	148
C9—H9···Cg1ii	0.93	2.95	3.603 (5)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 tolyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.79 (4)	2.32 (4)	3.099 (5)	171 (3)
C14—H14A⋯O1i	0.96	2.48	3.334 (6)	148
C9—H9⋯Cg1ii	0.93	2.95	3.603 (5)	128

Symmetry codes: (i) ; (ii) .