1,3-Bis(2-nitro­phen­oxy)propan-2-ol

Xiao, Z.-Y.; Tang, W.-H.; Wang, S.-Y.

doi:10.1107/S1600536811000250

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o357

doi:10.1107/S1600536811000250

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1,3-Bis(2-nitrophenoxy)propan-2-ol

Zhi-You Xiao,^a ^* Wen-Hua Tang ^a and Shao-Yun Wang ^a

^aSchool of Environment and Life Sciences, Kaili University, Kaili, Guizhou 556000, People's Republic of China
^*Correspondence e-mail: gzzhiyoux@126.com

(Received 8 December 2010; accepted 4 January 2011; online 12 January 2011)

In the title compound, C₁₅H₁₄N₂O₇, the planes of the two benzene rings form a dihedral angle of 33.16 (17)°. In the crystal, intermolecular hydrogen bonds involveing the OH group and nitro O atoms link the molecules into chains propagating along the a axis.

Related literature

For a related structure, see: Elizondo et al. (2009 ). For general background to the use of amines as intermediates in the preparation of dyes, herbicides, pesticides, and pharmaceuticals, see: Downing et al. (1997 ); Tafesh et al. (1996 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₇
M_r = 334.28
Tetragonal, P 2₁ 2₁ 2₁
a = 7.287 (4) Å
c = 28.158 (17) Å
V = 1495.2 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.22 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.974, T_max = 0.979
10200 measured reflections
1570 independent reflections
1022 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.103
S = 0.96
1570 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O6ⁱ	0.82	2.43	3.079 (4)	137
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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/S1600536811000250/bq2262sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000250/bq2262Isup2.hkl

checkCIF report

Comment top

Aromatic nitro compounds can be reduced to the corresponding amines, which are important intermediates in the preparation of dyes, herbicides, pesticides, and pharmaceuticals (Tafesh et al., 1996; Downing et al., 1997; Elizondo et al. 2009). Herein we report the crystal structure of the title compound. The crystal structure of the title compound is represented in Fig. 1. The aromatic rings in a molecule are not coplanar, and the planes of two benzene rings form dihedral angle of 33.16 (17) °. the nitro groups are twisted out of the planes of their attached benzene rings, and the dihedral angles are 30.8 (2) and 24.25 (19), respectively. The O—H···O hydrogen bonds are observed between OH-group and the nitro groups O atom, the distance of the O4—H4A···O6 hydrogen bonds is 3.079 (4) Å(Table 1). These intermolecular H-bond links the molecules into supramolecular structure, and crystal packing of the title compound is shown in Fig. 2.

Related literature top

For a related structure, see: Elizondo et al. (2009). For general background to the use of amines as intermediates in the preparation of dyes, herbicides, pesticides, and pharmaceuticals, see: Downing et al. (1997); Tafesh et al. (1996).

Experimental top

Epichlorohydrin (2.31 g, 0.025 mol) was added slowly to a stirred solution of NaOH (2.0 g,0.05 mol), O-nitrophenol (6.95 g,0.05 mol) in water (40 ml) at 60°C over a period of 40 min, and the solution was stirred at 60°C for 3 h, then the solvent was removed by reduced pressure filter, the solid product was rinsed with 30 ml water, then the crude product was dissolved in 50 ml 95% ethanol solution, and then set aside for five days to obtain 3.1 g light yellow crystals, in a yield of 36%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed down the a axis.
	Fig. 3. Intermolecular hydrogen link the molecules into a chains propagating along a axis. Hydrogen bonds are shown with dashed lines.

1,3-Bis(2-nitrophenoxy)propan-2-ol top

Crystal data top

C₁₅H₁₄N₂O₇	D_x = 1.485 Mg m⁻³
M_r = 334.28	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P2₁2₁2₁	Cell parameters from 1570 reflections
Hall symbol: P 2ac 2ab	θ = 1.5–25.0°
a = 7.287 (4) Å	µ = 0.12 mm⁻¹
c = 28.158 (17) Å	T = 293 K
V = 1495.2 (13) Å³	Block, yellow
Z = 4	0.22 × 0.19 × 0.18 mm
F(000) = 696

Data collection top

Bruker SMART CCD area-detector diffractometer	1570 independent reflections
Radiation source: fine-focus sealed tube	1022 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→8
T_min = 0.974, T_max = 0.979	k = −8→8
10200 measured reflections	l = −33→32

Refinement top

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0581P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
1570 reflections	Δρ_max = 0.15 e Å⁻³
218 parameters	Δρ_min = −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: 0.0123 (17)

Crystal data top

C₁₅H₁₄N₂O₇	Z = 4
M_r = 334.28	Mo Kα radiation
Tetragonal, P2₁2₁2₁	µ = 0.12 mm⁻¹
a = 7.287 (4) Å	T = 293 K
c = 28.158 (17) Å	0.22 × 0.19 × 0.18 mm
V = 1495.2 (13) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	1570 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1022 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.979	R_int = 0.062
10200 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 0.96	Δρ_max = 0.15 e Å⁻³
1570 reflections	Δρ_min = −0.15 e Å⁻³
218 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	0.0232 (5)	0.8105 (5)	0.40291 (10)	0.0467 (9)
C2	−0.1155 (6)	0.8419 (5)	0.43548 (12)	0.0594 (10)
H2	−0.0936	0.8266	0.4678	0.071*
C3	−0.2854 (6)	0.8957 (5)	0.41980 (14)	0.0709 (12)
H3	−0.3794	0.9164	0.4415	0.085*
C4	−0.3162 (6)	0.9188 (6)	0.37265 (14)	0.0698 (11)
H4	−0.4329	0.9519	0.3623	0.084*
C5	−0.1785 (5)	0.8944 (5)	0.33975 (12)	0.0589 (10)
H5	−0.2014	0.9155	0.3077	0.071*
C6	−0.0061 (5)	0.8383 (5)	0.35432 (10)	0.0476 (9)
C7	0.1259 (5)	0.8721 (5)	0.27648 (9)	0.0539 (10)
H7A	0.1111	1.0041	0.2742	0.065*
H7B	0.0226	0.8130	0.2610	0.065*
C8	0.3040 (5)	0.8121 (5)	0.25460 (11)	0.0552 (9)
H8	0.4052	0.8645	0.2731	0.066*
C9	0.3240 (4)	0.8721 (5)	0.20369 (10)	0.0561 (10)
H9A	0.3520	1.0021	0.2023	0.067*
H9B	0.4230	0.8051	0.1885	0.067*
C10	0.1474 (5)	0.8550 (5)	0.13208 (10)	0.0433 (8)
C11	−0.0153 (4)	0.8131 (5)	0.10830 (10)	0.0427 (8)
C12	−0.0277 (5)	0.8204 (5)	0.05975 (11)	0.0576 (10)
H12	−0.1371	0.7895	0.0447	0.069*
C13	0.1211 (6)	0.8731 (5)	0.03335 (11)	0.0629 (11)
H13	0.1133	0.8780	0.0004	0.076*
C14	0.2825 (6)	0.9190 (5)	0.05595 (11)	0.0576 (10)
H14	0.3828	0.9573	0.0381	0.069*
C15	0.2969 (5)	0.9087 (4)	0.10472 (11)	0.0504 (9)
H15	0.4074	0.9379	0.1194	0.060*
N1	0.2012 (4)	0.7496 (4)	0.42086 (10)	0.0571 (8)
N2	−0.1829 (4)	0.7619 (4)	0.13400 (11)	0.0553 (8)
O1	0.2440 (4)	0.7981 (4)	0.46074 (9)	0.0978 (11)
O2	0.2959 (4)	0.6490 (4)	0.39666 (9)	0.0702 (8)
O3	0.1401 (3)	0.8157 (4)	0.32490 (7)	0.0598 (7)
O4	0.3173 (4)	0.6194 (3)	0.25628 (7)	0.0711 (8)
H4A	0.3071	0.5847	0.2839	0.107*
O5	0.1533 (3)	0.8355 (3)	0.17982 (7)	0.0510 (6)
O6	−0.2026 (3)	0.8110 (4)	0.17517 (8)	0.0701 (8)
O7	−0.2971 (4)	0.6716 (4)	0.11246 (10)	0.0813 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (2)	0.045 (2)	0.0417 (18)	−0.0052 (19)	0.0001 (17)	−0.0017 (15)
C2	0.072 (3)	0.056 (2)	0.050 (2)	−0.007 (2)	0.014 (2)	−0.0026 (19)
C3	0.068 (3)	0.065 (3)	0.080 (3)	0.000 (3)	0.030 (2)	−0.005 (2)
C4	0.059 (3)	0.069 (3)	0.081 (3)	0.011 (2)	0.008 (2)	0.003 (2)
C5	0.058 (3)	0.062 (2)	0.057 (2)	0.009 (2)	0.000 (2)	0.0034 (18)
C6	0.047 (2)	0.050 (2)	0.0457 (19)	−0.0015 (19)	0.0053 (17)	−0.0067 (16)
C7	0.061 (2)	0.065 (2)	0.0355 (17)	0.006 (2)	−0.0027 (16)	−0.0052 (16)
C8	0.050 (2)	0.072 (3)	0.0440 (18)	−0.005 (2)	−0.0023 (18)	−0.0010 (18)
C9	0.042 (2)	0.082 (3)	0.0443 (19)	−0.010 (2)	−0.0042 (16)	0.0027 (18)
C10	0.047 (2)	0.047 (2)	0.0362 (17)	0.0020 (19)	0.0045 (16)	0.0021 (14)
C11	0.042 (2)	0.045 (2)	0.0414 (17)	0.0013 (17)	0.0007 (16)	−0.0012 (16)
C12	0.065 (2)	0.063 (3)	0.0451 (19)	0.003 (2)	−0.0075 (19)	−0.0072 (18)
C13	0.084 (3)	0.067 (3)	0.0380 (19)	0.012 (3)	0.003 (2)	0.0003 (18)
C14	0.059 (3)	0.063 (2)	0.050 (2)	0.004 (2)	0.017 (2)	0.0098 (18)
C15	0.046 (2)	0.059 (2)	0.0457 (18)	0.000 (2)	0.0048 (17)	0.0058 (17)
N1	0.058 (2)	0.069 (2)	0.0447 (17)	−0.0081 (19)	−0.0046 (16)	0.0048 (15)
N2	0.0434 (19)	0.061 (2)	0.0613 (19)	0.0023 (18)	−0.0029 (17)	0.0045 (16)
O1	0.104 (2)	0.144 (3)	0.0458 (15)	−0.002 (2)	−0.0294 (15)	−0.0091 (16)
O2	0.0593 (18)	0.0792 (19)	0.0721 (16)	0.0094 (18)	−0.0089 (14)	−0.0002 (15)
O3	0.0565 (15)	0.0866 (18)	0.0363 (12)	0.0130 (15)	0.0000 (11)	0.0020 (12)
O4	0.0822 (19)	0.0783 (19)	0.0527 (14)	0.0236 (17)	0.0045 (13)	0.0071 (12)
O5	0.0410 (13)	0.0744 (16)	0.0377 (12)	−0.0050 (13)	−0.0011 (10)	0.0034 (11)
O6	0.0509 (16)	0.105 (2)	0.0544 (14)	−0.0034 (17)	0.0118 (13)	0.0020 (15)
O7	0.0492 (17)	0.089 (2)	0.105 (2)	−0.0169 (18)	−0.0067 (16)	−0.0063 (18)

Geometric parameters (Å, º) top

C1—C2	1.383 (4)	C9—H9A	0.9700
C1—C6	1.399 (4)	C9—H9B	0.9700
C1—N1	1.461 (4)	C10—O5	1.352 (3)
C2—C3	1.372 (5)	C10—C15	1.390 (4)
C2—H2	0.9300	C10—C11	1.396 (4)
C3—C4	1.357 (5)	C11—C12	1.371 (4)
C3—H3	0.9300	C11—N2	1.468 (4)
C4—C5	1.378 (5)	C12—C13	1.370 (5)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.383 (5)	C13—C14	1.378 (5)
C5—H5	0.9300	C13—H13	0.9300
C6—O3	1.359 (4)	C14—C15	1.379 (4)
C7—O3	1.428 (3)	C14—H14	0.9300
C7—C8	1.502 (4)	C15—H15	0.9300
C7—H7A	0.9700	N1—O2	1.216 (3)
C7—H7B	0.9700	N1—O1	1.218 (3)
C8—O4	1.408 (4)	N2—O6	1.222 (3)
C8—C9	1.506 (4)	N2—O7	1.222 (3)
C8—H8	0.9800	O4—H4A	0.8200
C9—O5	1.439 (3)

C2—C1—C6	120.9 (3)	C8—C9—H9A	110.1
C2—C1—N1	118.0 (3)	O5—C9—H9B	110.1
C6—C1—N1	121.2 (3)	C8—C9—H9B	110.1
C3—C2—C1	119.5 (3)	H9A—C9—H9B	108.4
C3—C2—H2	120.2	O5—C10—C15	123.8 (3)
C1—C2—H2	120.2	O5—C10—C11	118.7 (3)
C4—C3—C2	120.0 (4)	C15—C10—C11	117.5 (3)
C4—C3—H3	120.0	C12—C11—C10	121.7 (3)
C2—C3—H3	120.0	C12—C11—N2	116.5 (3)
C3—C4—C5	121.4 (4)	C10—C11—N2	121.8 (3)
C3—C4—H4	119.3	C13—C12—C11	120.0 (3)
C5—C4—H4	119.3	C13—C12—H12	120.0
C4—C5—C6	120.0 (3)	C11—C12—H12	120.0
C4—C5—H5	120.0	C12—C13—C14	119.5 (3)
C6—C5—H5	120.0	C12—C13—H13	120.2
O3—C6—C5	124.5 (3)	C14—C13—H13	120.2
O3—C6—C1	117.3 (3)	C13—C14—C15	120.7 (3)
C5—C6—C1	118.1 (3)	C13—C14—H14	119.6
O3—C7—C8	104.2 (3)	C15—C14—H14	119.6
O3—C7—H7A	110.9	C14—C15—C10	120.5 (3)
C8—C7—H7A	110.9	C14—C15—H15	119.7
O3—C7—H7B	110.9	C10—C15—H15	119.7
C8—C7—H7B	110.9	O2—N1—O1	123.1 (3)
H7A—C7—H7B	108.9	O2—N1—C1	119.6 (3)
O4—C8—C7	109.6 (3)	O1—N1—C1	117.3 (3)
O4—C8—C9	108.4 (3)	O6—N2—O7	123.3 (3)
C7—C8—C9	112.9 (3)	O6—N2—C11	119.4 (3)
O4—C8—H8	108.6	O7—N2—C11	117.3 (3)
C7—C8—H8	108.6	C6—O3—C7	119.3 (3)
C9—C8—H8	108.6	C8—O4—H4A	109.5
O5—C9—C8	107.9 (3)	C10—O5—C9	118.2 (2)
O5—C9—H9A	110.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O6ⁱ	0.82	2.43	3.079 (4)	137

Symmetry code: (i) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₇
M_r	334.28
Crystal system, space group	Tetragonal, P2₁2₁2₁
Temperature (K)	293
a, c (Å)	7.287 (4), 28.158 (17)
V (Å³)	1495.2 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.22 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.974, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	10200, 1570, 1022
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.103, 0.96
No. of reflections	1570
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
O4—H4A···O6ⁱ	0.82	2.43	3.079 (4)	137.1

Symmetry code: (i) −x, y−1/2, −z+1/2.

Acknowledgements

We acknowledge the support of the Natural Science Foundation of Kaili University (Z0914).

References

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