1,3-Bis(2-nitro-phen-oxy)propan-2-ol.

In the title compound, C(15)H(14)N(2)O(7), the planes of the two benzene rings form a dihedral angle of 33.16 (17)°. In the crystal, inter-molecular hydrogen bonds involveing the OH group and nitro O atoms link the mol-ecules 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 = 334.28

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.103

S = 0.96

1570 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000250/bq2262sup1.cif

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

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

C15H14N2O7	Dx = 1.485 Mg m−3
Mr = 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

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

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(Fo2) + (0.0581P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
1570 reflections	Δρmax = 0.15 e Å−3
218 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: 0.0123 (17)

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	0.0232 (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)

	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)

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

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

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) .