4-[3-(4-Nitro­phen­oxy)prop­oxy]aniline

Zheng, L.-M.; Wei, X.; Peng, X.-R.; Zeng, J.-P.; Zhang, Y.-Q.

doi:10.1107/S1600536808032406

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2110

doi:10.1107/S1600536808032406

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4-[3-(4-Nitrophenoxy)propoxy]aniline

Li-Mei Zheng,^a Xian Wei,^b Xiao-Rong Peng,^b Jin-Ping Zeng ^b and Yun-Qian Zhang ^b ^*

^aSchool of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, People's Republic of China, and ^bKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China
^*Correspondence e-mail: sci.yqzhang@gzu.edu.cn

(Received 27 September 2008; accepted 7 October 2008; online 15 October 2008)

The molecules of the title compound, C₁₅H₁₆N₂O₄, are linked via N—H⋯O hydrogen bonds, forming undulating one-dimensional chains. Adjacent chains are linked by weak C—H⋯π interactions, 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_r = 288.30
Orthorhombic, P c c n
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.126
S = 1.05
2509 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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⋯Cg2^iv	0.93	3.01	3.757 (4)	139
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y, z-{\script{3\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iv) $[-x-{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 phenyl rings, respectively

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 ).

Supporting information

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

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

checkCIF report

Comment top

As part of our ongoing investigation on bibenzene compound, we present the crystal structure of the title compound (I) containing multiple functional groups that can develop strong interactions with cucurbit[n]urils (CB[n]) (Freeman et al., 1981; Day & Arnold, 2000; Day et al., 2002; Kim et al., 2000)

The crystal structure of (I) is shown in Fig.1. Two phenyl rings were linked by ethereal chain forming a non-coplanar structure and the dihedral angle between two phenyl ring is 26.13 (9) Å. Molecules are linked via N2—H2B···O1 hydrogen bonds forming a undulant one-dimensional chains (Fig. 2) and adjacent chains are linked by C—H···π interaction forming a three-dimensional framework (Table 1, Cg1 and Cg2 are centroids of the phenyl ring (C1—C6) and (C10—C15), respectively).

Related literature top

For general background, see: Day & Arnold (2000); Day et al. (2002); Freeman et al. (1981); Kim et al. (2000). Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 phenyl rings, respectively

Experimental top

P-toluenesulfonyl chloride (7.62 g, 40 mmol) was added slowly, whilst stirring, to a pyridine solution (50 ml) containing 1,3-propanediol (1.52 g, 20 mmol). The mixture was stirred for about 4 h in the range of 268 K - 278 K. Water (40 ml) was added to the resulting solution, the precipitate was collected by filtration, the solid product was crystallized using ethanol. The solid product (6.85 g, 20 mmol) dissolved in DMF (100 ml) containing K₂CO₃ (2 g), p-nitrophenol (0.54 g, 4 mmol) was added slowly, to the DMF(100 ml) solution, and the mixture was heated at 353 K for 24 h, and then the solvent was removed into water and filtered, the residue was washed with water, and 1,3-bis(-nitrylphenoxy)-propane was obtained. Hydrazine (30 g,80%) was added slowly to a stirred solution of ethanol (50 ml) containing 1,4-bis(-nitrylphenoxy)-propane (3.12 g, 10 mmol), FeCl₃.6H₂O (0.8 g) and active carbon (1.8 g) at 348 K for 5 h, and then the solvent was filtered, the solid product was crystallized using ethanol, Single crystals of (I) were obtained after a week.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of (I). Hydrogen bonds are shown as dashed lines.

4-[3-(4-Nitrophenoxy)propoxy]aniline top

Crystal data top

C₁₅H₁₆N₂O₄	F(000) = 1216
M_r = 288.30	D_x = 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

Data collection top

Bruker APEXII CCD area-detector diffractometer	2509 independent reflections
Radiation source: fine-focus sealed tube	1554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.978, T_max = 0.984	k = −37→41
17736 measured reflections	l = −8→9

Refinement top

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(F_o²) + (0.0596P)²] where P = (F_o² + 2F_c²)/3
2509 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O₄	V = 2857 (4) Å³
M_r = 288.30	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 10.808 (8) Å	µ = 0.10 mm⁻¹
b = 34.79 (3) Å	T = 298 K
c = 7.596 (6) Å	0.23 × 0.19 × 0.16 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2509 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1554 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.984	R_int = 0.065
17736 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.05	Δρ_max = 0.25 e Å⁻³
2509 reflections	Δρ_min = −0.16 e Å⁻³
190 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg2^iv	0.93	3.01	3.757 (4)	139

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1/2, y, z−3/2; (iii) x, −y−1/2, z−3/2; (iv) −x−1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₄
M_r	288.30
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	298
a, b, c (Å)	10.808 (8), 34.79 (3), 7.596 (6)
V (Å³)	2857 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.19 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.978, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	17736, 2509, 1554
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.126, 1.05
No. of reflections	2509
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.16

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1ⁱ	0.86	2.29	3.123 (3)	163.6
C3—H3···Cg1ⁱⁱ	0.93	3.07	3.513 (4)	111.3
C7—H7B···Cg2ⁱⁱⁱ	0.97	2.71	3.567 (4)	148.1
C13—H13···Cg2^iv	0.93	3.01	3.757 (4)	138.5

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1/2, y, z−3/2; (iii) x, −y−1/2, z−3/2; (iv) −x−1/2, y, z−1/2.

Acknowledgements

We acknowledge the support of the National Natural Science Foundation of China (No. 20662003) and the Foundation of the Governor of Guizhou Province, China.

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