4-Meth-oxy-N-phenyl-aniline.

In the mol-ecule of the title compound, C(13)H(13)NO, the two benzene rings are oriented at a dihedral angle of 59.9 (2)°. In the crystal structure, the benzene rings of neighbouring mol-ecules are oriented nearly parallel or perpendicular, making dihedral angles of 2.8 (2) and 79.5 (2)°, respectively. The crystal structure is stabilized by a network of C-H⋯π and N-H⋯π inter-actions.

Related literature

For general background, see: Acheson (1973 ▶); Gatto et al. (2006 ▶); Li et al. (2002 ▶); Oettmeier & Renger (1980 ▶); Razavi & McCapra (2000 ▶); Steiner (2000 ▶); Takahashi et al. (2001 ▶); Velusamy et al. (2005 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Rodriguez & Bunge (2003 ▶).

Experimental

Crystal data

C13H13NO

M = 199.24

Orthorhombic,

a = 15.090 (3) Å

b = 18.394 (4) Å

c = 7.596 (2) Å

V = 2108.4 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 295 (2) K

0.05 × 0.03 × 0.02 mm

Data collection

Kuma KM-4 diffractometer

Absorption correction: none

2443 measured reflections

1851 independent reflections

1005 reflections with I > 2σ(I)

R int = 0.035

3 standard reflections every 200 reflections intensity decay: 0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.131

S = 0.99

1851 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: KM-4 Software (Oxford Diffraction, 2003 ▶); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039457/hk2570sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039457/hk2570Isup2.hkl

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

C13H13NO	F(000) = 848
Mr = 199.24	Dx = 1.255 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 50 reflections
a = 15.090 (3) Å	θ = 2.2–25°
b = 18.394 (4) Å	µ = 0.08 mm−1
c = 7.596 (2) Å	T = 295 K
V = 2108.4 (8) Å3	Block, colorless
Z = 8	0.05 × 0.03 × 0.02 mm

Kuma KM-4 diffractometer	Rint = 0.035
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.2°
graphite	h = 0→17
θ/2θ scans	k = −21→0
2443 measured reflections	l = −9→2
1851 independent reflections	3 standard reflections every 200 reflections
1005 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.081P)2 + 0.0542P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
1851 reflections	Δρmax = 0.16 e Å−3
138 parameters	Δρmin = −0.15 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: 0.015 (2)

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.

	x	y	z	Uiso*/Ueq
C1	0.49051 (14)	0.32843 (9)	0.6655 (3)	0.0526 (6)
C2	0.52660 (14)	0.36650 (10)	0.8048 (3)	0.0533 (5)
H2	0.5861	0.3794	0.8010	0.064*
C3	0.47688 (12)	0.38576 (10)	0.9489 (3)	0.0500 (5)
H3	0.5025	0.4117	1.0409	0.060*
C4	0.38875 (13)	0.36634 (10)	0.9558 (3)	0.0491 (5)
C5	0.35215 (14)	0.32732 (10)	0.8191 (3)	0.0553 (6)
H5	0.2930	0.3133	0.8244	0.066*
C6	0.40192 (15)	0.30921 (10)	0.6763 (3)	0.0577 (6)
H6	0.3760	0.2835	0.5843	0.069*
N7	0.54179 (14)	0.30655 (9)	0.5208 (2)	0.0679 (6)
H7	0.5415	0.2610	0.4954	0.082*
C8	0.59269 (13)	0.35133 (11)	0.4155 (3)	0.0488 (5)
C9	0.59081 (13)	0.42662 (10)	0.4292 (3)	0.0535 (5)
H9	0.5561	0.4486	0.5153	0.064*
C10	0.63953 (16)	0.46850 (13)	0.3170 (3)	0.0701 (7)
H10	0.6377	0.5188	0.3279	0.084*
C11	0.69087 (19)	0.43785 (18)	0.1892 (3)	0.0882 (9)
H11	0.7233	0.4669	0.1124	0.106*
C12	0.69399 (16)	0.36363 (17)	0.1759 (3)	0.0809 (8)
H12	0.7291	0.3422	0.0897	0.097*
C13	0.64619 (14)	0.32079 (13)	0.2877 (3)	0.0633 (6)
H13	0.6497	0.2705	0.2777	0.076*
O14	0.33254 (9)	0.38212 (8)	1.0914 (2)	0.0671 (5)
C15	0.36725 (18)	0.41960 (15)	1.2379 (3)	0.0809 (7)
H15A	0.3220	0.4246	1.3260	0.121*
H15B	0.3871	0.4669	1.2018	0.121*
H15C	0.4162	0.3928	1.2857	0.121*

	U11	U22	U33	U12	U13	U23
C1	0.0758 (14)	0.0385 (10)	0.0434 (11)	−0.0006 (9)	0.0030 (11)	0.0020 (9)
C2	0.0537 (11)	0.0521 (11)	0.0542 (13)	−0.0044 (9)	0.0006 (10)	−0.0014 (9)
C3	0.0555 (11)	0.0497 (10)	0.0448 (11)	−0.0027 (9)	−0.0027 (10)	−0.0019 (9)
C4	0.0534 (11)	0.0462 (10)	0.0475 (11)	0.0004 (9)	0.0005 (10)	0.0042 (9)
C5	0.0531 (12)	0.0536 (11)	0.0593 (14)	−0.0081 (9)	−0.0085 (11)	0.0039 (10)
C6	0.0764 (15)	0.0458 (11)	0.0510 (13)	−0.0124 (10)	−0.0146 (11)	0.0016 (10)
N7	0.1075 (14)	0.0417 (8)	0.0546 (11)	−0.0010 (9)	0.0181 (11)	−0.0072 (8)
C8	0.0529 (11)	0.0553 (11)	0.0383 (10)	0.0050 (8)	−0.0078 (9)	−0.0012 (9)
C9	0.0610 (12)	0.0523 (11)	0.0471 (12)	0.0029 (9)	−0.0039 (10)	0.0022 (10)
C10	0.0821 (16)	0.0706 (14)	0.0577 (15)	−0.0181 (12)	−0.0034 (13)	0.0091 (12)
C11	0.0803 (17)	0.125 (2)	0.0595 (17)	−0.0421 (17)	0.0081 (14)	−0.0006 (16)
C12	0.0543 (13)	0.126 (2)	0.0622 (16)	−0.0077 (14)	0.0080 (12)	−0.0266 (15)
C13	0.0589 (13)	0.0755 (14)	0.0556 (13)	0.0104 (11)	−0.0050 (11)	−0.0181 (12)
O14	0.0578 (9)	0.0794 (10)	0.0642 (10)	−0.0026 (7)	0.0064 (7)	−0.0103 (8)
C15	0.0766 (15)	0.1028 (18)	0.0634 (16)	0.0028 (14)	0.0076 (14)	−0.0203 (15)

C1—C2	1.381 (3)	C8—C9	1.389 (3)
C1—C6	1.385 (3)	C9—C10	1.364 (3)
C1—N7	1.403 (3)	C9—H9	0.9300
C2—C3	1.373 (3)	C10—C11	1.364 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.378 (3)	C11—C12	1.370 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—O14	1.365 (2)	C12—C13	1.365 (3)
C4—C5	1.378 (3)	C12—H12	0.9300
C5—C6	1.361 (3)	C13—H13	0.9300
C5—H5	0.9300	O14—C15	1.410 (3)
C6—H6	0.9300	C15—H15A	0.9600
N7—C8	1.381 (3)	C15—H15B	0.9600
N7—H7	0.8600	C15—H15C	0.9600
C8—C13	1.382 (3)
C2—C1—C6	117.68 (19)	C13—C8—C9	118.0 (2)
C2—C1—N7	121.9 (2)	C10—C9—C8	120.4 (2)
C6—C1—N7	120.36 (19)	C10—C9—H9	119.8
C3—C2—C1	121.74 (19)	C8—C9—H9	119.8
C3—C2—H2	119.1	C9—C10—C11	121.1 (2)
C1—C2—H2	119.1	C9—C10—H10	119.4
C2—C3—C4	119.42 (19)	C11—C10—H10	119.4
C2—C3—H3	120.3	C10—C11—C12	119.0 (2)
C4—C3—H3	120.3	C10—C11—H11	120.5
O14—C4—C3	125.00 (18)	C12—C11—H11	120.5
O14—C4—C5	115.48 (17)	C13—C12—C11	120.8 (2)
C3—C4—C5	119.52 (19)	C13—C12—H12	119.6
C6—C5—C4	120.48 (18)	C11—C12—H12	119.6
C6—C5—H5	119.8	C12—C13—C8	120.7 (2)
C4—C5—H5	119.8	C12—C13—H13	119.6
C5—C6—C1	121.15 (19)	C8—C13—H13	119.6
C5—C6—H6	119.4	C4—O14—C15	117.9 (2)
C1—C6—H6	119.4	O14—C15—H15A	109.5
C1—N7—C8	126.1 (2)	O14—C15—H15B	109.5
C8—N7—H7	116.9	H15A—C15—H15B	109.5
C1—N7—H7	116.9	O14—C15—H15C	109.5
N7—C8—C13	119.30 (19)	H15A—C15—H15C	109.5
N7—C8—C9	122.67 (18)	H15B—C15—H15C	109.5
C6—C1—C2—C3	−0.8 (3)	C1—N7—C8—C13	174.0 (2)
N7—C1—C2—C3	−177.82 (17)	C1—N7—C8—C9	−7.8 (3)
C1—C2—C3—C4	0.4 (3)	N7—C8—C9—C10	−177.21 (19)
C2—C3—C4—O14	179.92 (17)	C13—C8—C9—C10	1.1 (3)
C2—C3—C4—C5	0.6 (3)	C8—C9—C10—C11	0.1 (3)
O14—C4—C5—C6	179.34 (17)	C9—C10—C11—C12	−0.9 (4)
C3—C4—C5—C6	−1.3 (3)	C10—C11—C12—C13	0.4 (4)
C4—C5—C6—C1	0.9 (3)	C11—C12—C13—C8	0.8 (4)
C2—C1—C6—C5	0.1 (3)	N7—C8—C13—C12	176.8 (2)
N7—C1—C6—C5	177.18 (18)	C9—C8—C13—C12	−1.5 (3)
C2—C1—N7—C8	−55.5 (3)	C3—C4—O14—C15	−1.6 (3)
C6—C1—N7—C8	127.6 (2)	C5—C4—O14—C15	177.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg2i	0.93	2.91	3.671 (2)	139
N7—H7···Cg1ii	0.86	2.88	3.593 (2)	142
C10—H10···Cg1iii	0.93	2.92	3.723 (3)	145

Table 1

C—H⋯π and N—H⋯π inter­actions (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg2i	0.93	2.91	3.671 (2)	139
N7—H7⋯Cg1ii	0.86	2.88	3.593 (2)	142
C10—H10⋯Cg1iii	0.93	2.92	3.723 (3)	145

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C6 ring and C8–C13 rings, respectively.