4-Meth-oxy-N-(4-nitro-benz-yl)aniline.

In the title compound, C(14)H(14)N(2)O(3), the nitro group is nearly coplanar with the benzene ring to which it is bonded [dihedral angle = 1.70 (2)°], and this ring is para-substituted by the amino-methyl-ene group. The dihedral angle between the benzene rings is 57.8 (1)°. The crystal structure is stabilized by N-H⋯O and C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions are also observed.

Related literature

For related structures, see: Iwasaki et al. (1988 ▶). For the biological properties of aldimines, see: Rjosk & Neumann (1971 ▶); Hillesheim et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H14N2O3

M = 258.27

Monoclinic,

a = 7.4993 (3) Å

b = 17.1516 (7) Å

c = 10.0048 (5) Å

β = 96.861 (4)°

V = 1277.65 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.955, T max = 1.000

11435 measured reflections

2511 independent reflections

1692 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.05

2511 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200846X/bh2415sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200846X/bh2415Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200846X/bh2415Isup3.cml

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

C14H14N2O3	F(000) = 544
Mr = 258.27	Dx = 1.343 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4747 reflections
a = 7.4993 (3) Å	θ = 3.6–29.0°
b = 17.1516 (7) Å	µ = 0.10 mm−1
c = 10.0048 (5) Å	T = 293 K
β = 96.861 (4)°	Block, red
V = 1277.65 (10) Å3	0.3 × 0.2 × 0.1 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2511 independent reflections
Radiation source: fine-focus sealed tube	1692 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.6°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −21→21
Tmin = 0.955, Tmax = 1.000	l = −12→12
11435 measured reflections

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.2077P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2511 reflections	Δρmax = 0.18 e Å−3
178 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0116 (18)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	−0.2703 (2)	0.01096 (11)	0.2223 (2)	0.0948 (6)
O2	−0.3470 (3)	0.12998 (13)	0.2161 (3)	0.1390 (10)
N1	−0.2400 (2)	0.07908 (13)	0.24933 (19)	0.0695 (5)
C1	0.2618 (2)	0.14226 (11)	0.45527 (19)	0.0499 (5)
C2	0.2220 (3)	0.06469 (12)	0.4248 (2)	0.0581 (5)
H2	0.3072	0.0265	0.4505	0.070*
C3	0.0581 (3)	0.04336 (11)	0.3571 (2)	0.0550 (5)
H3	0.0320	−0.0086	0.3367	0.066*
C4	−0.0654 (2)	0.10088 (11)	0.32049 (18)	0.0491 (5)
C5	−0.0304 (3)	0.17839 (12)	0.3476 (2)	0.0563 (5)
H5	−0.1155	0.2165	0.3210	0.068*
C6	0.1338 (3)	0.19793 (11)	0.4152 (2)	0.0547 (5)
H6	0.1593	0.2501	0.4344	0.066*
C7	0.4411 (3)	0.16668 (12)	0.5260 (2)	0.0636 (6)
H7A	0.5284	0.1668	0.4619	0.076*
H7B	0.4319	0.2195	0.5592	0.076*
N8	0.5039 (2)	0.11659 (10)	0.63639 (18)	0.0597 (5)
C9	0.6719 (2)	0.13024 (10)	0.71064 (19)	0.0464 (5)
C10	0.7998 (2)	0.17809 (11)	0.66267 (19)	0.0511 (5)
H10	0.7719	0.2042	0.5814	0.061*
C11	0.9671 (3)	0.18720 (11)	0.73402 (19)	0.0531 (5)
H11	1.0507	0.2194	0.7000	0.064*
C12	1.0133 (2)	0.14945 (10)	0.85483 (19)	0.0485 (5)
C13	0.8871 (3)	0.10262 (10)	0.90428 (19)	0.0510 (5)
H13	0.9152	0.0772	0.9863	0.061*
C14	0.7188 (2)	0.09308 (10)	0.83278 (19)	0.0505 (5)
H14	0.6354	0.0610	0.8674	0.061*
O15	1.18447 (17)	0.16348 (8)	0.91664 (14)	0.0652 (4)
C16	1.2455 (3)	0.12020 (13)	1.0336 (2)	0.0724 (7)
H16A	1.1723	0.1321	1.1034	0.109*
H16B	1.3681	0.1337	1.0633	0.109*
H16C	1.2375	0.0655	1.0135	0.109*
H8	0.421 (3)	0.0966 (13)	0.683 (2)	0.072 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0735 (11)	0.0908 (13)	0.1143 (15)	−0.0263 (10)	−0.0125 (10)	−0.0124 (11)
O2	0.0739 (12)	0.1245 (17)	0.199 (3)	0.0363 (13)	−0.0627 (14)	−0.0507 (16)
N1	0.0484 (10)	0.0889 (14)	0.0686 (12)	0.0022 (11)	−0.0032 (9)	−0.0163 (11)
C1	0.0495 (11)	0.0541 (11)	0.0451 (11)	−0.0046 (9)	0.0008 (8)	0.0047 (8)
C2	0.0502 (11)	0.0527 (11)	0.0680 (14)	0.0079 (9)	−0.0063 (9)	0.0017 (10)
C3	0.0534 (11)	0.0500 (11)	0.0604 (13)	−0.0011 (9)	0.0020 (9)	−0.0047 (9)
C4	0.0407 (10)	0.0625 (12)	0.0435 (11)	0.0003 (9)	0.0030 (8)	−0.0043 (9)
C5	0.0539 (12)	0.0570 (12)	0.0570 (12)	0.0117 (10)	0.0021 (9)	0.0001 (10)
C6	0.0603 (12)	0.0471 (11)	0.0557 (12)	−0.0016 (9)	0.0029 (9)	0.0009 (9)
C7	0.0614 (13)	0.0599 (12)	0.0648 (14)	−0.0114 (10)	−0.0119 (10)	0.0118 (10)
N8	0.0488 (10)	0.0669 (11)	0.0601 (11)	−0.0124 (9)	−0.0074 (8)	0.0165 (9)
C9	0.0459 (10)	0.0408 (9)	0.0505 (11)	−0.0027 (8)	−0.0026 (8)	0.0000 (8)
C10	0.0549 (11)	0.0525 (11)	0.0442 (11)	−0.0055 (9)	−0.0011 (9)	0.0067 (9)
C11	0.0520 (11)	0.0520 (11)	0.0545 (12)	−0.0124 (9)	0.0033 (9)	0.0048 (9)
C12	0.0470 (10)	0.0426 (10)	0.0533 (12)	−0.0028 (8)	−0.0044 (9)	−0.0038 (8)
C13	0.0582 (12)	0.0454 (10)	0.0473 (11)	−0.0010 (9)	−0.0020 (9)	0.0067 (8)
C14	0.0503 (11)	0.0457 (10)	0.0544 (12)	−0.0075 (9)	0.0017 (9)	0.0081 (9)
O15	0.0553 (8)	0.0660 (9)	0.0688 (10)	−0.0128 (7)	−0.0150 (7)	0.0086 (7)
C16	0.0653 (13)	0.0741 (14)	0.0711 (15)	−0.0024 (12)	−0.0196 (11)	0.0062 (12)

O1—N1	1.214 (2)	N8—C9	1.404 (2)
O2—N1	1.206 (2)	N8—H8	0.89 (2)
N1—C4	1.462 (2)	C9—C14	1.386 (2)
C1—C6	1.379 (3)	C9—C10	1.390 (3)
C1—C2	1.389 (3)	C10—C11	1.377 (2)
C1—C7	1.502 (2)	C10—H10	0.9300
C2—C3	1.380 (3)	C11—C12	1.378 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.373 (3)	C12—C13	1.378 (3)
C3—H3	0.9300	C12—O15	1.378 (2)
C4—C5	1.376 (3)	C13—C14	1.384 (2)
C5—C6	1.373 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	O15—C16	1.415 (2)
C7—N8	1.433 (2)	C16—H16A	0.9600
C7—H7A	0.9700	C16—H16B	0.9600
C7—H7B	0.9700	C16—H16C	0.9600
O2—N1—O1	122.31 (19)	C9—N8—H8	115.1 (14)
O2—N1—C4	118.5 (2)	C7—N8—H8	116.8 (14)
O1—N1—C4	119.17 (19)	C14—C9—C10	117.59 (16)
C6—C1—C2	118.38 (17)	C14—C9—N8	120.47 (16)
C6—C1—C7	119.78 (18)	C10—C9—N8	121.88 (17)
C2—C1—C7	121.81 (17)	C11—C10—C9	120.77 (17)
C3—C2—C1	121.14 (18)	C11—C10—H10	119.6
C3—C2—H2	119.4	C9—C10—H10	119.6
C1—C2—H2	119.4	C10—C11—C12	121.28 (17)
C4—C3—C2	118.24 (18)	C10—C11—H11	119.4
C4—C3—H3	120.9	C12—C11—H11	119.4
C2—C3—H3	120.9	C13—C12—O15	125.72 (17)
C3—C4—C5	122.36 (17)	C13—C12—C11	118.53 (16)
C3—C4—N1	118.84 (18)	O15—C12—C11	115.75 (16)
C5—C4—N1	118.80 (18)	C12—C13—C14	120.43 (17)
C6—C5—C4	118.15 (18)	C12—C13—H13	119.8
C6—C5—H5	120.9	C14—C13—H13	119.8
C4—C5—H5	120.9	C13—C14—C9	121.41 (17)
C5—C6—C1	121.73 (18)	C13—C14—H14	119.3
C5—C6—H6	119.1	C9—C14—H14	119.3
C1—C6—H6	119.1	C12—O15—C16	118.13 (15)
N8—C7—C1	112.89 (16)	O15—C16—H16A	109.5
N8—C7—H7A	109.0	O15—C16—H16B	109.5
C1—C7—H7A	109.0	H16A—C16—H16B	109.5
N8—C7—H7B	109.0	O15—C16—H16C	109.5
C1—C7—H7B	109.0	H16A—C16—H16C	109.5
H7A—C7—H7B	107.8	H16B—C16—H16C	109.5
C9—N8—C7	119.94 (16)
C6—C1—C2—C3	−0.5 (3)	C1—C7—N8—C9	178.22 (17)
C7—C1—C2—C3	−178.52 (19)	C7—N8—C9—C14	166.83 (19)
C1—C2—C3—C4	−0.1 (3)	C7—N8—C9—C10	−16.1 (3)
C2—C3—C4—C5	0.8 (3)	C14—C9—C10—C11	0.7 (3)
C2—C3—C4—N1	−179.66 (18)	N8—C9—C10—C11	−176.45 (18)
O2—N1—C4—C3	−179.1 (2)	C9—C10—C11—C12	−0.1 (3)
O1—N1—C4—C3	−1.3 (3)	C10—C11—C12—C13	−0.7 (3)
O2—N1—C4—C5	0.5 (3)	C10—C11—C12—O15	−179.83 (17)
O1—N1—C4—C5	178.3 (2)	O15—C12—C13—C14	179.92 (17)
C3—C4—C5—C6	−0.8 (3)	C11—C12—C13—C14	0.9 (3)
N1—C4—C5—C6	179.63 (17)	C12—C13—C14—C9	−0.3 (3)
C4—C5—C6—C1	0.1 (3)	C10—C9—C14—C13	−0.5 (3)
C2—C1—C6—C5	0.5 (3)	N8—C9—C14—C13	176.68 (17)
C7—C1—C6—C5	178.53 (18)	C13—C12—O15—C16	7.4 (3)
C6—C1—C7—N8	138.5 (2)	C11—C12—O15—C16	−173.61 (18)
C2—C1—C7—N8	−43.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O1i	0.89 (2)	2.42 (3)	3.231 (2)	152.8 (19)
C16—H16B···O2ii	0.96	2.47	3.372 (3)	155
C3—H3···Cg2iii	0.93	2.77	3.560 (2)	143
C6—H6···Cg2iv	0.93	2.87	3.524 (2)	129
C16—H16A···Cg1v	0.96	2.96	3.830 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the nitro­phenyl (C1–C6) and meth­oxy­phenyl (C9–C14) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O1i	0.89 (2)	2.42 (3)	3.231 (2)	152.8 (19)
C16—H16B⋯O2ii	0.96	2.47	3.372 (3)	155
C3—H3⋯Cg2iii	0.93	2.77	3.560 (2)	143
C6—H6⋯Cg2iv	0.93	2.87	3.524 (2)	129
C16—H16A⋯Cg1v	0.96	2.96	3.830 (2)	151

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