3-(2-Nitro-phen-oxy)phthalonitrile.

In the title compound, C(14)H(7)N(3)O(3), the dihedral angle between the two arene units is 62.57 (12)°.

Related literature

For related literature, see: Atalay et al. (2003 ▶, 2004 ▶); Cave et al. (1986 ▶); Köysal et al. (2004 ▶); Leznoff & Lever (1989–1996 ▶); McKeown (1998 ▶); Ocak Ískeleli (2007 ▶); Ocak et al. (2003 ▶), Sharman & van Lier(2003 ▶).

Experimental

Crystal data

C14H7N3O3

M = 265.23

Monoclinic,

a = 8.0814 (17) Å

b = 7.9899 (12) Å

c = 19.068 (3) Å

β = 95.944 (15)°

V = 1224.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 (2) K

0.4 × 0.4 × 0.1 mm

Data collection

Bruker P4 diffractometer

Absorption correction: none

3018 measured reflections

2155 independent reflections

1252 reflections with I > 2σ(I)

R int = 0.092

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.145

S = 1.03

2155 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.27 e Å−3

Data collection: XSCANS (Bruker, 1997 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067797/gd2031sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067797/gd2031Isup2.hkl

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

C14H7N3O3	F000 = 544
Mr = 265.23	Dx = 1.439 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 51 reflections
a = 8.0814 (17) Å	θ = 5.0–12.5º
b = 7.9899 (12) Å	µ = 0.11 mm−1
c = 19.068 (3) Å	T = 295 (2) K
β = 95.944 (15)º	Plate, colorless
V = 1224.6 (4) Å3	0.4 × 0.4 × 0.1 mm
Z = 4

Bruker P4 diffractometer	Rint = 0.092
Radiation source: fine-focus sealed tube	θmax = 25.0º
Monochromator: graphite	θmin = 2.2º
T = 295(2) K	h = −1→9
ω scans	k = −9→1
Absorption correction: none	l = −22→22
3018 measured reflections	3 standard reflections
2155 independent reflections	every 97 reflections
1252 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.001P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2155 reflections	Δρmax = 0.20 e Å−3
181 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.4115 (3)	0.5913 (3)	0.63769 (12)	0.0683 (8)
O2	0.5975 (4)	0.8586 (4)	0.66974 (15)	0.0806 (9)
O3	0.7869 (4)	0.8009 (4)	0.75304 (16)	0.0932 (11)
N1	0.0726 (6)	0.4464 (5)	0.36401 (19)	0.0967 (14)
N2	0.1821 (5)	0.7972 (5)	0.50408 (18)	0.0822 (11)
N3	0.6493 (4)	0.7811 (4)	0.72224 (17)	0.0609 (9)
C1	0.1511 (5)	0.4108 (5)	0.4142 (2)	0.0651 (11)
C2	0.2279 (5)	0.6648 (6)	0.51586 (18)	0.0566 (10)
C3	0.2487 (5)	0.3691 (5)	0.47972 (18)	0.0534 (9)
C4	0.2840 (4)	0.4955 (5)	0.53013 (17)	0.0492 (9)
C5	0.3749 (4)	0.4568 (5)	0.59366 (18)	0.0524 (9)
C6	0.4322 (5)	0.2954 (5)	0.6072 (2)	0.0623 (10)
H6A	0.4952	0.2702	0.6495	0.075*
C7	0.3950 (5)	0.1729 (5)	0.5576 (2)	0.0657 (11)
H7A	0.4328	0.0644	0.5667	0.079*
C8	0.3024 (5)	0.2082 (5)	0.49420 (19)	0.0620 (10)
H8A	0.2765	0.1234	0.4615	0.074*
C9	0.4213 (4)	0.5689 (5)	0.71071 (17)	0.0523 (9)
C10	0.5397 (4)	0.6628 (4)	0.75215 (18)	0.0480 (9)
C11	0.5535 (5)	0.6431 (5)	0.82497 (18)	0.0584 (10)
H11A	0.6334	0.7036	0.8530	0.070*
C12	0.4516 (5)	0.5362 (5)	0.85555 (19)	0.0603 (10)
H12A	0.4628	0.5220	0.9042	0.072*
C14	0.3162 (5)	0.4646 (5)	0.7422 (2)	0.0626 (11)
H14A	0.2348	0.4043	0.7148	0.075*
C13	0.3319 (5)	0.4496 (5)	0.8141 (2)	0.0643 (11)
H13A	0.2599	0.3792	0.8352	0.077*

	U11	U22	U33	U12	U13	U23
O1	0.090 (2)	0.0637 (18)	0.0462 (14)	−0.0149 (15)	−0.0149 (13)	−0.0003 (13)
O2	0.090 (2)	0.082 (2)	0.0670 (18)	−0.0169 (17)	−0.0075 (16)	0.0199 (16)
O3	0.0672 (19)	0.119 (3)	0.088 (2)	−0.0375 (19)	−0.0167 (17)	0.0071 (19)
N1	0.128 (4)	0.087 (3)	0.065 (2)	0.014 (3)	−0.036 (2)	−0.007 (2)
N2	0.113 (3)	0.067 (3)	0.063 (2)	0.008 (2)	−0.005 (2)	0.0033 (19)
N3	0.064 (2)	0.062 (2)	0.0549 (19)	−0.0103 (18)	−0.0035 (17)	−0.0013 (17)
C1	0.082 (3)	0.056 (2)	0.054 (2)	−0.005 (2)	−0.009 (2)	−0.0072 (19)
C2	0.065 (3)	0.062 (3)	0.0408 (19)	−0.002 (2)	−0.0030 (18)	−0.0008 (19)
C3	0.060 (2)	0.056 (2)	0.0429 (19)	−0.005 (2)	−0.0001 (17)	0.0012 (18)
C4	0.049 (2)	0.053 (2)	0.0451 (19)	−0.0043 (18)	0.0015 (15)	−0.0005 (17)
C5	0.056 (2)	0.056 (2)	0.0438 (19)	−0.006 (2)	0.0004 (17)	−0.0018 (18)
C6	0.064 (2)	0.068 (3)	0.053 (2)	0.001 (2)	−0.0055 (19)	0.006 (2)
C7	0.080 (3)	0.057 (2)	0.059 (2)	0.007 (2)	0.002 (2)	0.006 (2)
C8	0.076 (3)	0.057 (3)	0.053 (2)	0.000 (2)	0.004 (2)	−0.0059 (19)
C9	0.056 (2)	0.053 (2)	0.045 (2)	0.0009 (19)	−0.0076 (17)	0.0009 (17)
C10	0.049 (2)	0.043 (2)	0.050 (2)	0.0003 (17)	−0.0030 (16)	−0.0021 (16)
C11	0.062 (2)	0.059 (2)	0.051 (2)	−0.002 (2)	−0.0103 (19)	−0.0059 (18)
C12	0.065 (3)	0.068 (3)	0.047 (2)	−0.001 (2)	0.0039 (19)	−0.0027 (19)
C14	0.059 (2)	0.065 (3)	0.061 (2)	−0.016 (2)	−0.007 (2)	0.001 (2)
C13	0.066 (3)	0.065 (3)	0.062 (2)	−0.011 (2)	0.010 (2)	0.002 (2)

O1—C5	1.377 (4)	C6—H6A	0.9300
O1—C9	1.398 (4)	C7—C8	1.383 (5)
O2—N3	1.214 (4)	C7—H7A	0.9300
O3—N3	1.213 (4)	C8—H8A	0.9300
N1—C1	1.129 (5)	C9—C14	1.372 (5)
N2—C2	1.136 (5)	C9—C10	1.395 (5)
N3—C10	1.452 (5)	C10—C11	1.390 (5)
C1—C3	1.445 (5)	C11—C12	1.359 (5)
C2—C4	1.443 (6)	C11—H11A	0.9300
C3—C8	1.376 (5)	C12—C13	1.372 (5)
C3—C4	1.403 (5)	C12—H12A	0.9300
C4—C5	1.385 (5)	C14—C13	1.369 (5)
C5—C6	1.385 (5)	C14—H14A	0.9300
C6—C7	1.372 (5)	C13—H13A	0.9300
C5—O1—C9	119.6 (3)	C3—C8—C7	119.8 (3)
O3—N3—O2	123.6 (4)	C3—C8—H8A	120.1
O3—N3—C10	117.4 (3)	C7—C8—H8A	120.1
O2—N3—C10	119.0 (3)	C14—C9—C10	119.9 (3)
N1—C1—C3	178.2 (5)	C14—C9—O1	122.7 (3)
N2—C2—C4	179.1 (4)	C10—C9—O1	117.4 (3)
C8—C3—C4	119.8 (3)	C11—C10—C9	119.0 (4)
C8—C3—C1	121.4 (3)	C11—C10—N3	118.5 (3)
C4—C3—C1	118.7 (3)	C9—C10—N3	122.5 (3)
C5—C4—C3	119.3 (3)	C12—C11—C10	120.6 (3)
C5—C4—C2	120.1 (3)	C12—C11—H11A	119.7
C3—C4—C2	120.5 (3)	C10—C11—H11A	119.7
O1—C5—C4	114.8 (3)	C11—C12—C13	119.5 (4)
O1—C5—C6	124.5 (3)	C11—C12—H12A	120.3
C4—C5—C6	120.5 (3)	C13—C12—H12A	120.3
C7—C6—C5	119.4 (3)	C13—C14—C9	119.6 (4)
C7—C6—H6A	120.3	C13—C14—H14A	120.2
C5—C6—H6A	120.3	C9—C14—H14A	120.2
C6—C7—C8	121.1 (4)	C14—C13—C12	121.3 (4)
C6—C7—H7A	119.4	C14—C13—H13A	119.3
C8—C7—H7A	119.4	C12—C13—H13A	119.3