4-[3-(4-Nitro-phen-oxy)prop-oxy]aniline.

The mol-ecules of the title compound, C(15)H(16)N(2)O(4), are linked via N-H⋯O hydrogen bonds, forming undulating one-dimensional chains. Adjacent chains are linked by weak C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For general background, see: Day & Arnold (2000 ▶); Day et al. (2002 ▶); Freeman et al. (1981 ▶); Kim et al. (2000 ▶).

Experimental

Crystal data

C15H16N2O4

M = 288.30

Orthorhombic,

a = 10.808 (8) Å

b = 34.79 (3) Å

c = 7.596 (6) Å

V = 2857 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.23 × 0.19 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.978, T max = 0.984

17736 measured reflections

2509 independent reflections

1554 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.126

S = 1.05

2509 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032406/at2638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032406/at2638Isup2.hkl

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

C15H16N2O4	F(000) = 1216
Mr = 288.30	Dx = 1.341 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2509 reflections
a = 10.808 (8) Å	θ = 2.0–25.0°
b = 34.79 (3) Å	µ = 0.10 mm−1
c = 7.596 (6) Å	T = 298 K
V = 2857 (4) Å3	Prism, brown
Z = 8	0.23 × 0.19 × 0.16 mm

Bruker APEXII CCD area-detector diffractometer	2509 independent reflections
Radiation source: fine-focus sealed tube	1554 reflections with I > 2σ(I)
graphite	Rint = 0.065
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.978, Tmax = 0.984	k = −37→41
17736 measured reflections	l = −8→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0596P)2] where P = (Fo2 + 2Fc2)/3
2509 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.25 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
C1	0.3694 (2)	0.52612 (6)	0.2758 (3)	0.0531 (6)
C2	0.4692 (2)	0.54418 (6)	0.1976 (3)	0.0587 (6)
H2	0.5427	0.5308	0.1793	0.070*
C3	0.2592 (2)	0.54512 (6)	0.3021 (3)	0.0575 (6)
H3	0.1926	0.5326	0.3541	0.069*
C4	0.4590 (2)	0.58237 (6)	0.1467 (3)	0.0528 (6)
H4	0.5259	0.5949	0.0950	0.063*
C5	0.2486 (2)	0.58278 (6)	0.2507 (3)	0.0556 (6)
H5	0.1743	0.5957	0.2676	0.067*
C6	0.3483 (2)	0.60180 (6)	0.1735 (3)	0.0468 (5)
C7	0.4269 (2)	0.66196 (6)	0.0598 (3)	0.0540 (6)
H7A	0.4487	0.6531	−0.0571	0.065*
H7B	0.4994	0.6600	0.1346	0.065*
C8	0.3816 (2)	0.70308 (6)	0.0527 (3)	0.0577 (6)
H8A	0.3102	0.7046	−0.0244	0.069*
H8B	0.3558	0.7110	0.1695	0.069*
C9	0.4804 (2)	0.73000 (5)	−0.0131 (3)	0.0539 (6)
H9A	0.5580	0.7249	0.0468	0.065*
H9B	0.4929	0.7264	−0.1384	0.065*
C10	0.5238 (2)	0.79809 (6)	−0.0124 (3)	0.0459 (5)
C11	0.6378 (2)	0.79332 (6)	−0.0955 (3)	0.0507 (6)
H11	0.6630	0.7690	−0.1311	0.061*
C12	0.4878 (2)	0.83474 (6)	0.0389 (3)	0.0493 (6)
H12	0.4117	0.8383	0.0935	0.059*
C13	0.7136 (2)	0.82491 (6)	−0.1252 (3)	0.0534 (6)
H13	0.7894	0.8214	−0.1808	0.064*
C14	0.5645 (2)	0.86604 (6)	0.0094 (3)	0.0512 (6)
H14	0.5393	0.8903	0.0455	0.061*
C15	0.6788 (2)	0.86171 (6)	−0.0736 (3)	0.0487 (5)
N1	0.3792 (2)	0.48636 (6)	0.3322 (3)	0.0763 (7)
N2	0.75855 (17)	0.89324 (5)	−0.0993 (3)	0.0694 (6)
H2A	0.8298	0.8898	−0.1474	0.083*
H2B	0.7361	0.9159	−0.0669	0.083*
O1	0.29183 (19)	0.47143 (5)	0.4107 (3)	0.1127 (8)
O2	0.4737 (2)	0.46834 (5)	0.3007 (4)	0.1200 (9)
O3	0.32733 (13)	0.63919 (4)	0.1305 (2)	0.0590 (4)
O4	0.44110 (13)	0.76862 (4)	0.0214 (2)	0.0570 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0549 (15)	0.0357 (14)	0.0687 (15)	0.0006 (11)	−0.0019 (12)	0.0067 (11)
C2	0.0491 (15)	0.0477 (15)	0.0793 (17)	0.0004 (12)	0.0011 (12)	0.0025 (12)
C3	0.0561 (16)	0.0499 (15)	0.0664 (15)	−0.0045 (12)	0.0055 (12)	0.0072 (12)
C4	0.0490 (14)	0.0455 (14)	0.0640 (15)	−0.0046 (11)	−0.0003 (11)	0.0053 (11)
C5	0.0505 (15)	0.0487 (15)	0.0677 (15)	0.0011 (12)	0.0070 (12)	0.0050 (12)
C6	0.0545 (14)	0.0361 (13)	0.0496 (13)	−0.0013 (11)	−0.0073 (11)	0.0021 (10)
C7	0.0594 (15)	0.0428 (14)	0.0598 (14)	−0.0065 (11)	−0.0049 (12)	0.0052 (10)
C8	0.0602 (15)	0.0445 (14)	0.0684 (15)	−0.0038 (11)	−0.0088 (12)	0.0069 (11)
C9	0.0666 (16)	0.0383 (13)	0.0566 (14)	0.0025 (11)	−0.0009 (11)	0.0040 (10)
C10	0.0493 (14)	0.0380 (13)	0.0504 (12)	0.0008 (11)	−0.0028 (10)	0.0031 (10)
C11	0.0524 (14)	0.0404 (13)	0.0594 (14)	0.0082 (11)	0.0000 (12)	−0.0023 (10)
C12	0.0513 (14)	0.0453 (14)	0.0514 (13)	0.0054 (11)	0.0031 (10)	−0.0005 (10)
C13	0.0493 (14)	0.0524 (15)	0.0584 (14)	0.0026 (11)	0.0019 (11)	0.0001 (11)
C14	0.0615 (15)	0.0391 (13)	0.0530 (14)	0.0025 (11)	−0.0022 (12)	−0.0065 (10)
C15	0.0500 (14)	0.0465 (14)	0.0495 (12)	−0.0027 (11)	−0.0038 (11)	0.0005 (10)
N1	0.0723 (17)	0.0485 (15)	0.1081 (18)	0.0008 (12)	0.0043 (14)	0.0138 (12)
N2	0.0672 (13)	0.0544 (13)	0.0867 (15)	−0.0160 (11)	0.0080 (11)	−0.0116 (11)
O1	0.0956 (16)	0.0661 (13)	0.176 (2)	−0.0062 (11)	0.0244 (15)	0.0501 (13)
O2	0.0921 (15)	0.0634 (14)	0.205 (3)	0.0244 (12)	0.0344 (16)	0.0389 (14)
O3	0.0557 (9)	0.0410 (9)	0.0805 (11)	−0.0021 (7)	−0.0004 (8)	0.0110 (8)
O4	0.0583 (10)	0.0381 (9)	0.0745 (11)	0.0006 (8)	0.0061 (8)	0.0040 (7)

C1—C3	1.377 (3)	C9—O4	1.433 (2)
C1—C2	1.383 (3)	C9—H9A	0.9700
C1—N1	1.453 (3)	C9—H9B	0.9700
C2—C4	1.388 (3)	C10—O4	1.385 (2)
C2—H2	0.9300	C10—C12	1.389 (3)
C3—C5	1.372 (3)	C10—C11	1.393 (3)
C3—H3	0.9300	C11—C13	1.390 (3)
C4—C6	1.390 (3)	C11—H11	0.9300
C4—H4	0.9300	C12—C14	1.387 (3)
C5—C6	1.394 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—C15	1.391 (3)
C6—O3	1.361 (3)	C13—H13	0.9300
C7—O3	1.440 (2)	C14—C15	1.394 (3)
C7—C8	1.513 (3)	C14—H14	0.9300
C7—H7A	0.9700	C15—N2	1.409 (3)
C7—H7B	0.9700	N1—O2	1.221 (2)
C8—C9	1.506 (3)	N1—O1	1.232 (3)
C8—H8A	0.9700	N2—H2A	0.8600
C8—H8B	0.9700	N2—H2B	0.8600
C3—C1—C2	121.3 (2)	O4—C9—H9A	110.1
C3—C1—N1	118.6 (2)	C8—C9—H9A	110.1
C2—C1—N1	120.1 (2)	O4—C9—H9B	110.1
C1—C2—C4	119.5 (2)	C8—C9—H9B	110.1
C1—C2—H2	120.2	H9A—C9—H9B	108.4
C4—C2—H2	120.2	O4—C10—C12	116.53 (19)
C5—C3—C1	119.3 (2)	O4—C10—C11	124.51 (19)
C5—C3—H3	120.4	C12—C10—C11	119.0 (2)
C1—C3—H3	120.4	C13—C11—C10	120.0 (2)
C2—C4—C6	119.6 (2)	C13—C11—H11	120.0
C2—C4—H4	120.2	C10—C11—H11	120.0
C6—C4—H4	120.2	C14—C12—C10	120.5 (2)
C3—C5—C6	120.6 (2)	C14—C12—H12	119.7
C3—C5—H5	119.7	C10—C12—H12	119.7
C6—C5—H5	119.7	C11—C13—C15	121.5 (2)
O3—C6—C4	124.99 (19)	C11—C13—H13	119.3
O3—C6—C5	115.26 (19)	C15—C13—H13	119.3
C4—C6—C5	119.8 (2)	C12—C14—C15	121.17 (19)
O3—C7—C8	106.95 (18)	C12—C14—H14	119.4
O3—C7—H7A	110.3	C15—C14—H14	119.4
C8—C7—H7A	110.3	C13—C15—C14	117.81 (19)
O3—C7—H7B	110.3	C13—C15—N2	120.8 (2)
C8—C7—H7B	110.3	C14—C15—N2	121.4 (2)
H7A—C7—H7B	108.6	O2—N1—O1	121.3 (2)
C9—C8—C7	111.73 (19)	O2—N1—C1	119.5 (2)
C9—C8—H8A	109.3	O1—N1—C1	119.2 (2)
C7—C8—H8A	109.3	C15—N2—H2A	120.0
C9—C8—H8B	109.3	C15—N2—H2B	120.0
C7—C8—H8B	109.3	H2A—N2—H2B	120.0
H8A—C8—H8B	107.9	C6—O3—C7	119.42 (17)
O4—C9—C8	108.19 (18)	C10—O4—C9	117.95 (17)
C3—C1—C2—C4	0.9 (3)	C10—C11—C13—C15	0.0 (3)
N1—C1—C2—C4	−179.1 (2)	C10—C12—C14—C15	0.6 (3)
C2—C1—C3—C5	−0.4 (4)	C11—C13—C15—C14	0.0 (3)
N1—C1—C3—C5	179.5 (2)	C11—C13—C15—N2	177.85 (19)
C1—C2—C4—C6	−0.6 (3)	C12—C14—C15—C13	−0.3 (3)
C1—C3—C5—C6	−0.3 (3)	C12—C14—C15—N2	−178.14 (19)
C2—C4—C6—O3	179.49 (19)	C3—C1—N1—O2	175.7 (2)
C2—C4—C6—C5	−0.1 (3)	C2—C1—N1—O2	−4.4 (4)
C3—C5—C6—O3	−179.1 (2)	C3—C1—N1—O1	−4.1 (4)
C3—C5—C6—C4	0.6 (3)	C2—C1—N1—O1	175.8 (2)
O3—C7—C8—C9	177.80 (17)	C4—C6—O3—C7	−3.4 (3)
C7—C8—C9—O4	−167.07 (17)	C5—C6—O3—C7	176.24 (18)
O4—C10—C11—C13	179.26 (19)	C8—C7—O3—C6	−171.25 (17)
C12—C10—C11—C13	0.3 (3)	C12—C10—O4—C9	−173.68 (17)
O4—C10—C12—C14	−179.64 (18)	C11—C10—O4—C9	7.3 (3)
C11—C10—C12—C14	−0.6 (3)	C8—C9—O4—C10	173.62 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1i	0.86	2.29	3.123 (3)	164
C3—H3···Cg1ii	0.93	3.07	3.513 (4)	111
C7—H7B···Cg2iii	0.97	2.71	3.567 (4)	148
C13—H13···Cg2iv	0.93	3.01	3.757 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1i	0.86	2.29	3.123 (3)	164
C3—H3⋯Cg1ii	0.93	3.07	3.513 (4)	111
C7—H7B⋯Cg2iii	0.97	2.71	3.567 (4)	148
C13—H13⋯Cg2iv	0.93	3.01	3.757 (4)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 phenyl rings, respectively