4-(4-Nitro-benz-yl)pyridine.

The title compound, C12H10N2O2, has a twisted conformation, with a dihedral angle between the planes of the pyridine and benzene rings of 78.4 (2)°. The nitro group is coplanar with the attached benzene ring within experimental error. The mol-ecules form centrosymmetric dimers via Car-H⋯O inter-actions (H⋯O = 2.49 Å) and the dimers are π-stacked along the b axis [the separation between ring centroids is 3.788 (2) Å].

Related literature

For adducts of the title compound with different organic acids, see: Smith et al. (1997 ▶); Smith & Wermuth (2010 ▶, 2013 ▶). For a zinc complex of the title compound, see: Smith et al. (2011 ▶). For the analysis of π-stacking inter­actions, see: Dolomanov et al. (2009 ▶).

Experimental

Crystal data

C12H10N2O2

M = 214.22

Monoclinic,

a = 11.4138 (9) Å

b = 6.1241 (5) Å

c = 15.5812 (13) Å

β = 104.561 (9)°

V = 1054.13 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.4 × 0.2 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.770, T max = 1.000

4351 measured reflections

2136 independent reflections

1514 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.106

S = 1.03

2136 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017145/ld2106sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017145/ld2106Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017145/ld2106Isup3.cml

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

C12H10N2O2	F(000) = 448
Mr = 214.22	Dx = 1.350 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 949 reflections
a = 11.4138 (9) Å	θ = 3.3–29.0°
b = 6.1241 (5) Å	µ = 0.09 mm−1
c = 15.5812 (13) Å	T = 293 K
β = 104.561 (9)°	Needle, white
V = 1054.13 (15) Å3	0.4 × 0.2 × 0.15 mm
Z = 4

Agilent Xcalibur Eos diffractometer	2136 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1514 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.0534 pixels mm-1	θmax = 26.3°, θmin = 3.6°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −7→6
Tmin = 0.770, Tmax = 1.000	l = −19→19
4351 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.1216P] where P = (Fo2 + 2Fc2)/3
2136 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. Absorption correction CrysAlis PRO (Agilent, 2011). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
N2	0.13729 (12)	0.2522 (2)	0.13717 (9)	0.0459 (4)
C10	0.15049 (13)	0.1215 (2)	0.06150 (10)	0.0361 (4)
C9	0.11079 (14)	0.2054 (3)	−0.02263 (11)	0.0413 (4)
H9A	0.0757	0.3433	−0.0317	0.050*
C7	0.17562 (14)	−0.1248 (3)	−0.08069 (10)	0.0391 (4)
O2	0.09206 (12)	0.4333 (2)	0.12370 (9)	0.0633 (4)
C11	0.20080 (14)	−0.0837 (3)	0.07671 (11)	0.0410 (4)
H11A	0.2258	−0.1390	0.1340	0.049*
C8	0.12404 (14)	0.0808 (3)	−0.09329 (11)	0.0427 (4)
H8A	0.0978	0.1361	−0.1505	0.051*
C12	0.21313 (14)	−0.2047 (3)	0.00541 (11)	0.0426 (4)
H12A	0.2473	−0.3433	0.0149	0.051*
C6	0.19074 (15)	−0.2601 (3)	−0.15842 (11)	0.0496 (5)
H6A	0.1457	−0.3953	−0.1607	0.059*
H6B	0.1576	−0.1809	−0.2130	0.059*
O1	0.17074 (16)	0.1747 (2)	0.21073 (9)	0.0835 (5)
C3	0.32183 (15)	−0.3119 (3)	−0.15136 (10)	0.0445 (4)
C4	0.37349 (17)	−0.5080 (3)	−0.11888 (12)	0.0555 (5)
H4A	0.3263	−0.6168	−0.1028	0.067*
N1	0.56897 (15)	−0.3995 (3)	−0.13144 (12)	0.0712 (5)
C2	0.39748 (17)	−0.1617 (3)	−0.17558 (13)	0.0610 (5)
H2A	0.3676	−0.0274	−0.1992	0.073*
C5	0.49444 (19)	−0.5428 (4)	−0.11034 (14)	0.0670 (6)
H5A	0.5263	−0.6770	−0.0881	0.080*
C1	0.51831 (19)	−0.2128 (4)	−0.16440 (15)	0.0731 (6)
H1B	0.5676	−0.1088	−0.1812	0.088*

	U11	U22	U33	U12	U13	U23
N2	0.0485 (9)	0.0470 (9)	0.0436 (9)	0.0015 (7)	0.0142 (7)	−0.0001 (7)
C10	0.0327 (8)	0.0392 (9)	0.0376 (9)	−0.0024 (7)	0.0108 (7)	0.0001 (7)
C9	0.0387 (9)	0.0401 (9)	0.0448 (10)	0.0031 (7)	0.0098 (8)	0.0074 (8)
C7	0.0308 (8)	0.0477 (10)	0.0398 (9)	−0.0043 (7)	0.0104 (7)	−0.0016 (8)
O2	0.0808 (10)	0.0477 (8)	0.0618 (9)	0.0179 (7)	0.0189 (7)	−0.0018 (7)
C11	0.0430 (9)	0.0428 (9)	0.0363 (9)	0.0032 (8)	0.0086 (8)	0.0070 (8)
C8	0.0424 (9)	0.0498 (10)	0.0350 (9)	−0.0003 (8)	0.0082 (8)	0.0064 (8)
C12	0.0396 (9)	0.0385 (9)	0.0494 (10)	0.0037 (7)	0.0109 (8)	0.0026 (8)
C6	0.0413 (10)	0.0621 (11)	0.0455 (10)	−0.0024 (8)	0.0113 (8)	−0.0088 (9)
O1	0.1380 (14)	0.0749 (10)	0.0378 (8)	0.0326 (10)	0.0224 (8)	0.0078 (7)
C3	0.0436 (9)	0.0551 (11)	0.0361 (9)	−0.0042 (9)	0.0126 (8)	−0.0120 (8)
C4	0.0519 (11)	0.0561 (11)	0.0601 (12)	−0.0023 (9)	0.0172 (10)	−0.0061 (10)
N1	0.0481 (10)	0.0950 (14)	0.0719 (12)	0.0042 (10)	0.0176 (9)	−0.0145 (11)
C2	0.0540 (12)	0.0668 (13)	0.0653 (13)	−0.0035 (10)	0.0211 (10)	0.0019 (11)
C5	0.0585 (13)	0.0708 (14)	0.0692 (14)	0.0117 (12)	0.0114 (11)	−0.0119 (11)
C1	0.0535 (13)	0.0956 (17)	0.0759 (15)	−0.0169 (13)	0.0271 (12)	−0.0053 (14)

N2—O1	1.2101 (17)	C6—C3	1.506 (2)
N2—O2	1.2194 (17)	C6—H6A	0.9700
N2—C10	1.464 (2)	C6—H6B	0.9700
C10—C9	1.374 (2)	C3—C4	1.377 (2)
C10—C11	1.377 (2)	C3—C2	1.378 (2)
C9—C8	1.379 (2)	C4—C5	1.370 (3)
C9—H9A	0.9300	C4—H4A	0.9300
C7—C8	1.383 (2)	N1—C5	1.320 (3)
C7—C12	1.391 (2)	N1—C1	1.325 (3)
C7—C6	1.513 (2)	C2—C1	1.382 (3)
C11—C12	1.372 (2)	C2—H2A	0.9300
C11—H11A	0.9300	C5—H5A	0.9300
C8—H8A	0.9300	C1—H1B	0.9300
C12—H12A	0.9300
O1—N2—O2	122.59 (15)	C3—C6—H6A	109.3
O1—N2—C10	118.47 (14)	C7—C6—H6A	109.3
O2—N2—C10	118.93 (14)	C3—C6—H6B	109.3
C9—C10—C11	121.90 (15)	C7—C6—H6B	109.3
C9—C10—N2	119.20 (14)	H6A—C6—H6B	108.0
C11—C10—N2	118.89 (14)	C4—C3—C2	116.31 (17)
C10—C9—C8	118.60 (15)	C4—C3—C6	122.41 (16)
C10—C9—H9A	120.7	C2—C3—C6	121.27 (17)
C8—C9—H9A	120.7	C5—C4—C3	119.94 (18)
C8—C7—C12	118.32 (15)	C5—C4—H4A	120.0
C8—C7—C6	121.02 (15)	C3—C4—H4A	120.0
C12—C7—C6	120.66 (15)	C5—N1—C1	115.11 (18)
C12—C11—C10	118.48 (15)	C3—C2—C1	119.2 (2)
C12—C11—H11A	120.8	C3—C2—H2A	120.4
C10—C11—H11A	120.8	C1—C2—H2A	120.4
C9—C8—C7	121.25 (15)	N1—C5—C4	124.7 (2)
C9—C8—H8A	119.4	N1—C5—H5A	117.6
C7—C8—H8A	119.4	C4—C5—H5A	117.6
C11—C12—C7	121.44 (15)	N1—C1—C2	124.7 (2)
C11—C12—H12A	119.3	N1—C1—H1B	117.7
C7—C12—H12A	119.3	C2—C1—H1B	117.7
C3—C6—C7	111.59 (13)
O1—N2—C10—C9	178.75 (15)	C6—C7—C12—C11	179.59 (14)
O2—N2—C10—C9	−0.5 (2)	C8—C7—C6—C3	119.47 (17)
O1—N2—C10—C11	−0.3 (2)	C12—C7—C6—C3	−60.7 (2)
O2—N2—C10—C11	−179.55 (15)	C7—C6—C3—C4	98.12 (19)
C11—C10—C9—C8	−1.2 (2)	C7—C6—C3—C2	−80.4 (2)
N2—C10—C9—C8	179.84 (13)	C2—C3—C4—C5	1.5 (3)
C9—C10—C11—C12	1.2 (2)	C6—C3—C4—C5	−177.18 (16)
N2—C10—C11—C12	−179.81 (13)	C4—C3—C2—C1	−1.4 (3)
C10—C9—C8—C7	0.2 (2)	C6—C3—C2—C1	177.24 (17)
C12—C7—C8—C9	0.6 (2)	C1—N1—C5—C4	−1.2 (3)
C6—C7—C8—C9	−179.57 (14)	C3—C4—C5—N1	−0.1 (3)
C10—C11—C12—C7	−0.3 (2)	C5—N1—C1—C2	1.3 (3)
C8—C7—C12—C11	−0.6 (2)	C3—C2—C1—N1	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2i	0.93	2.49	3.302 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2i	0.93	2.49	3.302 (2)	146

Symmetry code: (i) .