4-Nitro-phthalo-nitrile.

In the title compound, C8H3N3O2 (systematic name: 4-nitro-benzene-1,2-dicarbo-nitrile), the nitro group is twisted out of the plane of the benzene ring to which it is attached [O-N-Cring-Cring torsion angle = 9.80 (13)°]. In the crystal packing, supra-molecular layers with a zigzag topology in the ac plane are sustained by C-H⋯N inter-actions.

Related literature

For background to the synthesis of functional phthalocyanines, see: Chin et al. (2012 ▶). For a related structure, see: Lin et al. (2006 ▶). For the synthesis, see: Rasmussen et al. (1978 ▶).

Experimental

Crystal data

C8H3N3O2

M = 173.13

Orthorhombic,

a = 12.8642 (3) Å

b = 9.2013 (2) Å

c = 13.2578 (3) Å

V = 1569.29 (6) Å3

Z = 8

Cu Kα radiation

μ = 0.94 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.626, T max = 1.000

7104 measured reflections

1638 independent reflections

1556 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.088

S = 1.10

1638 reflections

130 parameters

All H-atom parameters refined

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536814003468/wm5005sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003468/wm5005Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003468/wm5005Isup3.cml

CCDC reference: 987296

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H3N3O2	F(000) = 704
Mr = 173.13	Dx = 1.466 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4240 reflections
a = 12.8642 (3) Å	θ = 3.3–76.1°
b = 9.2013 (2) Å	µ = 0.94 mm−1
c = 13.2578 (3) Å	T = 100 K
V = 1569.29 (6) Å3	Prism, colourless
Z = 8	0.35 × 0.30 × 0.25 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	1638 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1556 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.016
Detector resolution: 10.4041 pixels mm-1	θmax = 76.3°, θmin = 6.7°
ω scan	h = −8→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −10→11
Tmin = 0.626, Tmax = 1.000	l = −16→16
7104 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	All H-atom parameters refined
S = 1.10	w = 1/[σ2(Fo2) + (0.0522P)2 + 0.3777P] where P = (Fo2 + 2Fc2)/3
1638 reflections	(Δ/σ)max < 0.001
130 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.24 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
O1	0.55783 (6)	0.56540 (8)	0.23140 (6)	0.0224 (2)
O2	0.41285 (6)	0.62811 (9)	0.16017 (6)	0.0284 (2)
N1	0.46305 (7)	0.56035 (9)	0.22296 (6)	0.0185 (2)
N2	0.49465 (7)	0.20831 (10)	0.59515 (7)	0.0245 (2)
N3	0.20184 (7)	0.10850 (10)	0.54001 (7)	0.0214 (2)
C1	0.40488 (7)	0.46610 (10)	0.29308 (7)	0.0159 (2)
C2	0.30038 (8)	0.44112 (11)	0.27448 (7)	0.0185 (2)
C3	0.24639 (7)	0.34933 (11)	0.33907 (7)	0.0183 (2)
C4	0.29752 (7)	0.28688 (10)	0.42094 (7)	0.0158 (2)
C5	0.40307 (7)	0.31687 (10)	0.43884 (7)	0.0152 (2)
C6	0.45807 (7)	0.40675 (10)	0.37365 (7)	0.0156 (2)
C7	0.45469 (7)	0.25464 (10)	0.52497 (7)	0.0176 (2)
C8	0.24319 (7)	0.18890 (10)	0.48760 (7)	0.0173 (2)
H2	0.2670 (11)	0.4827 (16)	0.2163 (10)	0.027 (3)*
H3	0.1745 (11)	0.3317 (13)	0.3282 (9)	0.020 (3)*
H6	0.5294 (10)	0.4254 (13)	0.3839 (9)	0.017 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0156 (4)	0.0246 (4)	0.0271 (4)	−0.0022 (3)	0.0032 (3)	0.0031 (3)
O2	0.0248 (4)	0.0300 (4)	0.0304 (4)	−0.0019 (3)	−0.0029 (3)	0.0151 (3)
N1	0.0177 (4)	0.0174 (4)	0.0204 (4)	−0.0004 (3)	0.0013 (3)	0.0015 (3)
N2	0.0198 (4)	0.0303 (5)	0.0235 (5)	0.0001 (3)	−0.0016 (3)	0.0064 (4)
N3	0.0183 (4)	0.0241 (4)	0.0217 (4)	−0.0026 (3)	0.0008 (3)	0.0014 (3)
C1	0.0166 (5)	0.0145 (4)	0.0167 (5)	0.0002 (3)	0.0030 (3)	−0.0003 (3)
C2	0.0176 (5)	0.0204 (5)	0.0174 (5)	0.0014 (3)	−0.0017 (3)	0.0002 (4)
C3	0.0132 (5)	0.0219 (5)	0.0199 (5)	−0.0009 (3)	−0.0010 (3)	−0.0005 (4)
C4	0.0155 (4)	0.0152 (4)	0.0166 (4)	−0.0002 (3)	0.0021 (3)	−0.0022 (3)
C5	0.0152 (4)	0.0144 (4)	0.0159 (4)	0.0021 (3)	−0.0001 (3)	−0.0020 (3)
C6	0.0125 (4)	0.0153 (4)	0.0190 (5)	0.0005 (3)	0.0006 (3)	−0.0021 (4)
C7	0.0135 (4)	0.0185 (5)	0.0208 (5)	−0.0015 (3)	0.0019 (3)	0.0000 (4)
C8	0.0139 (4)	0.0196 (5)	0.0184 (4)	0.0002 (3)	−0.0014 (3)	−0.0023 (4)

O1—N1	1.2252 (12)	C2—H2	0.962 (14)
O2—N1	1.2243 (11)	C3—C4	1.3932 (13)
N1—C1	1.4752 (12)	C3—H3	0.949 (13)
N2—C7	1.1453 (13)	C4—C5	1.4057 (13)
N3—C8	1.1459 (13)	C4—C8	1.4431 (13)
C1—C6	1.3811 (14)	C5—C6	1.3898 (13)
C1—C2	1.3859 (14)	C5—C7	1.4397 (13)
C2—C3	1.3889 (14)	C6—H6	0.943 (13)
O2—N1—O1	124.59 (8)	C3—C4—C5	120.44 (9)
O2—N1—C1	117.40 (8)	C3—C4—C8	120.41 (8)
O1—N1—C1	118.01 (8)	C5—C4—C8	119.15 (8)
C6—C1—C2	123.54 (9)	C6—C5—C4	120.23 (9)
C6—C1—N1	117.94 (8)	C6—C5—C7	119.68 (8)
C2—C1—N1	118.52 (9)	C4—C5—C7	120.09 (8)
C1—C2—C3	118.44 (9)	C1—C6—C5	117.66 (9)
C1—C2—H2	120.7 (8)	C1—C6—H6	121.4 (8)
C3—C2—H2	120.8 (8)	C5—C6—H6	120.9 (8)
C2—C3—C4	119.67 (9)	N2—C7—C5	178.04 (11)
C2—C3—H3	119.8 (8)	N3—C8—C4	178.30 (10)
C4—C3—H3	120.5 (8)
O2—N1—C1—C6	−170.25 (9)	C3—C4—C5—C7	178.52 (9)
O1—N1—C1—C6	9.80 (13)	C8—C4—C5—C7	−2.37 (13)
O2—N1—C1—C2	10.12 (13)	C2—C1—C6—C5	0.25 (14)
O1—N1—C1—C2	−169.82 (9)	N1—C1—C6—C5	−179.36 (8)
C6—C1—C2—C3	−1.26 (15)	C4—C5—C6—C1	1.09 (14)
N1—C1—C2—C3	178.34 (8)	C7—C5—C6—C1	−178.85 (8)
C1—C2—C3—C4	0.91 (15)	C6—C5—C7—N2	96 (3)
C2—C3—C4—C5	0.38 (14)	C4—C5—C7—N2	−84 (3)
C2—C3—C4—C8	−178.71 (9)	C3—C4—C8—N3	122 (3)
C3—C4—C5—C6	−1.41 (14)	C5—C4—C8—N3	−57 (4)
C8—C4—C5—C6	177.69 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N3i	0.962 (14)	2.621 (14)	3.3880 (13)	136.9 (11)
C3—H3···N2ii	0.950 (14)	2.554 (14)	3.3955 (13)	147.8 (10)
C6—H6···N3iii	0.943 (13)	2.457 (13)	3.3412 (13)	156.1 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N3i	0.962 (14)	2.621 (14)	3.3880 (13)	136.9 (11)
C3—H3⋯N2ii	0.950 (14)	2.554 (14)	3.3955 (13)	147.8 (10)
C6—H6⋯N3iii	0.943 (13)	2.457 (13)	3.3412 (13)	156.1 (10)

Symmetry codes: (i) ; (ii) ; (iii) .