2-(Naphthalen-2-yl-oxy)-5-nitro-pyridine.

A nearly orthogonal relationship is found for the ring systems in the title compound, C(15)H(10)N(2)O(3), with the dihedral angle between the rings being 86.13 (11)°. The nitro group is approximately coplanar with the pyridine ring to which it is connected [the O-N-C-C torsion angle = -1.8 (4)°]. This coplanarity allows for the close approach of these residues in the crystal structure enabling the formation of N-O⋯π(pyridine) inter-actions [3.547 (4) Å]. Further consolidation of the crystal packing is afforded by weak π-π inter-actions [centroid-centroid distances = 3.9576 (16) and 3.9822 (16) Å].

Related literature

For the structure of a related nitro­pyridine derivative, see: Nasir et al. (2010 ▶). For discussion on nitro-O⋯π inter­actions, see: Huang et al. (2008 ▶).

Experimental

Crystal data

C15H10N2O3

M = 266.25

Monoclinic,

a = 6.7389 (12) Å

b = 8.9182 (16) Å

c = 21.072 (4) Å

β = 94.289 (3)°

V = 1262.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.976, T max = 0.985

6512 measured reflections

2224 independent reflections

1052 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.193

S = 0.94

2224 reflections

158 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044060/hg5118sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044060/hg5118Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044060/hg5118Isup3.cml

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

C15H10N2O3	F(000) = 552
Mr = 266.25	Dx = 1.400 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1499 reflections
a = 6.7389 (12) Å	θ = 2.5–21.3°
b = 8.9182 (16) Å	µ = 0.10 mm−1
c = 21.072 (4) Å	T = 293 K
β = 94.289 (3)°	Block, colourless
V = 1262.9 (4) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Bruker SMART APEX diffractometer	2224 independent reflections
Radiation source: fine-focus sealed tube	1052 reflections with I > 2σ(I)
graphite	Rint = 0.052
ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.976, Tmax = 0.985	k = −9→10
6512 measured reflections	l = −23→25

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.193	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max = 0.001
2224 reflections	Δρmax = 0.26 e Å−3
158 parameters	Δρmin = −0.18 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: 0.024 (5)

	x	y	z	Uiso*/Ueq
O1	0.5816 (3)	0.6709 (3)	0.69203 (11)	0.0864 (8)
O2	0.8327 (5)	0.2782 (3)	0.47200 (13)	0.1210 (11)
O3	0.5363 (6)	0.1958 (4)	0.48260 (14)	0.1319 (12)
N1	0.4532 (4)	0.4809 (3)	0.62772 (12)	0.0709 (8)
N2	0.6776 (7)	0.2766 (4)	0.49811 (14)	0.0929 (10)
C1	0.6029 (5)	0.5686 (4)	0.64546 (14)	0.0662 (8)
C2	0.7856 (5)	0.5678 (4)	0.61964 (15)	0.0796 (10)
H2	0.8868	0.6323	0.6347	0.096*
C3	0.8131 (5)	0.4702 (4)	0.57165 (15)	0.0804 (10)
H3	0.9339	0.4653	0.5531	0.097*
C4	0.6578 (6)	0.3793 (3)	0.55143 (13)	0.0663 (9)
C5	0.4845 (6)	0.3863 (3)	0.58025 (15)	0.0747 (10)
H5	0.3819	0.3219	0.5662	0.090*
C6	0.41265 (19)	0.58487 (18)	0.78172 (8)	0.0638 (8)
H6	0.5213	0.5246	0.7941	0.077*
C7	0.4128 (2)	0.6695 (2)	0.72633 (7)	0.0638 (8)
C8	0.2505 (3)	0.75959 (18)	0.70776 (6)	0.0727 (9)
H8	0.2506	0.8162	0.6707	0.087*
C9	0.0879 (2)	0.76505 (16)	0.74459 (7)	0.0740 (9)
H9	−0.0208	0.8253	0.7322	0.089*
C10	0.08767 (17)	0.68042 (13)	0.79997 (6)	0.0565 (8)
C11	0.25006 (17)	0.59033 (13)	0.81854 (6)	0.0521 (7)
C12	0.2499 (3)	0.50569 (17)	0.87393 (7)	0.0714 (9)
H12	0.3585	0.4454	0.8863	0.086*
C13	0.0873 (3)	0.5111 (2)	0.91075 (7)	0.0822 (10)
H13	0.0872	0.4545	0.9478	0.099*
C14	−0.0751 (3)	0.6012 (2)	0.89219 (8)	0.0864 (11)
H14	−0.1839	0.6049	0.9168	0.104*
C15	−0.07492 (19)	0.6859 (2)	0.83680 (9)	0.0745 (10)
H15	−0.1836	0.7461	0.8244	0.089*

	U11	U22	U33	U12	U13	U23
O1	0.0829 (16)	0.0914 (17)	0.0898 (16)	−0.0342 (13)	0.0385 (13)	−0.0301 (14)
O2	0.158 (3)	0.121 (2)	0.089 (2)	0.032 (2)	0.0437 (19)	−0.0121 (16)
O3	0.164 (3)	0.118 (2)	0.110 (2)	−0.007 (2)	−0.016 (2)	−0.0479 (19)
N1	0.0775 (18)	0.0660 (17)	0.0704 (17)	−0.0159 (14)	0.0136 (14)	−0.0087 (14)
N2	0.133 (3)	0.083 (2)	0.062 (2)	0.023 (2)	0.000 (2)	−0.0026 (18)
C1	0.074 (2)	0.067 (2)	0.0588 (19)	−0.0110 (17)	0.0132 (16)	−0.0046 (16)
C2	0.073 (2)	0.094 (2)	0.074 (2)	−0.0240 (19)	0.0173 (18)	−0.012 (2)
C3	0.085 (3)	0.095 (3)	0.063 (2)	0.000 (2)	0.0180 (19)	0.003 (2)
C4	0.089 (3)	0.063 (2)	0.0475 (18)	0.0060 (18)	0.0089 (17)	0.0015 (15)
C5	0.092 (3)	0.065 (2)	0.067 (2)	−0.0149 (18)	0.0039 (19)	−0.0038 (17)
C6	0.0594 (19)	0.0561 (18)	0.075 (2)	0.0043 (14)	0.0001 (16)	−0.0062 (16)
C7	0.068 (2)	0.0581 (19)	0.066 (2)	−0.0146 (15)	0.0123 (16)	−0.0168 (16)
C8	0.090 (2)	0.061 (2)	0.064 (2)	−0.0162 (18)	−0.0125 (18)	0.0053 (16)
C9	0.064 (2)	0.069 (2)	0.086 (2)	0.0077 (16)	−0.0115 (18)	0.0010 (18)
C10	0.0562 (18)	0.0519 (17)	0.0608 (18)	0.0013 (14)	0.0011 (15)	−0.0056 (14)
C11	0.0529 (17)	0.0497 (16)	0.0535 (17)	0.0008 (13)	0.0023 (13)	−0.0044 (14)
C12	0.083 (2)	0.065 (2)	0.066 (2)	0.0065 (16)	0.0013 (18)	0.0028 (16)
C13	0.114 (3)	0.073 (2)	0.061 (2)	−0.008 (2)	0.016 (2)	0.0011 (17)
C14	0.077 (3)	0.094 (3)	0.092 (3)	−0.009 (2)	0.026 (2)	−0.022 (2)
C15	0.062 (2)	0.077 (2)	0.085 (2)	0.0101 (16)	0.0050 (18)	−0.0151 (19)

O1—C1	1.355 (3)	C6—H6	0.9300
O1—C7	1.393 (2)	C7—C8	1.3900
O2—N2	1.217 (4)	C8—C9	1.3900
O3—N2	1.219 (4)	C8—H8	0.9300
N1—C1	1.309 (4)	C9—C10	1.3900
N1—C5	1.337 (4)	C9—H9	0.9300
N2—C4	1.463 (4)	C10—C11	1.3900
C1—C2	1.383 (4)	C10—C15	1.3900
C2—C3	1.358 (4)	C11—C12	1.3900
C2—H2	0.9300	C12—C13	1.3900
C3—C4	1.366 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.3900
C4—C5	1.358 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.3900
C6—C7	1.3900	C14—H14	0.9300
C6—C11	1.3900	C15—H15	0.9300
C1—O1—C7	120.3 (2)	C8—C7—O1	120.35 (16)
C1—N1—C5	115.4 (3)	C7—C8—C9	120.0
O2—N2—O3	124.5 (4)	C7—C8—H8	120.0
O2—N2—C4	118.0 (4)	C9—C8—H8	120.0
O3—N2—C4	117.5 (4)	C10—C9—C8	120.0
N1—C1—O1	119.2 (3)	C10—C9—H9	120.0
N1—C1—C2	125.1 (3)	C8—C9—H9	120.0
O1—C1—C2	115.7 (3)	C9—C10—C11	120.0
C3—C2—C1	118.1 (3)	C9—C10—C15	120.0
C3—C2—H2	120.9	C11—C10—C15	120.0
C1—C2—H2	120.9	C12—C11—C10	120.0
C2—C3—C4	118.0 (3)	C12—C11—C6	120.0
C2—C3—H3	121.0	C10—C11—C6	120.0
C4—C3—H3	121.0	C13—C12—C11	120.0
C5—C4—C3	119.8 (3)	C13—C12—H12	120.0
C5—C4—N2	120.2 (4)	C11—C12—H12	120.0
C3—C4—N2	119.9 (3)	C12—C13—C14	120.0
N1—C5—C4	123.6 (3)	C12—C13—H13	120.0
N1—C5—H5	118.2	C14—C13—H13	120.0
C4—C5—H5	118.2	C15—C14—C13	120.0
C7—C6—C11	120.0	C15—C14—H14	120.0
C7—C6—H6	120.0	C13—C14—H14	120.0
C11—C6—H6	120.0	C14—C15—C10	120.0
C6—C7—C8	120.0	C14—C15—H15	120.0
C6—C7—O1	119.52 (16)	C10—C15—H15	120.0
C5—N1—C1—O1	178.1 (3)	C1—O1—C7—C8	−94.2 (3)
C5—N1—C1—C2	−1.0 (5)	C6—C7—C8—C9	0.0
C7—O1—C1—N1	8.4 (4)	O1—C7—C8—C9	−175.77 (15)
C7—O1—C1—C2	−172.4 (3)	C7—C8—C9—C10	0.0
N1—C1—C2—C3	0.8 (5)	C8—C9—C10—C11	0.0
O1—C1—C2—C3	−178.3 (3)	C8—C9—C10—C15	180.0
C1—C2—C3—C4	0.5 (5)	C9—C10—C11—C12	180.0
C2—C3—C4—C5	−1.4 (5)	C15—C10—C11—C12	0.0
C2—C3—C4—N2	177.5 (3)	C9—C10—C11—C6	0.0
O2—N2—C4—C5	177.1 (3)	C15—C10—C11—C6	180.0
O3—N2—C4—C5	−2.4 (5)	C7—C6—C11—C12	180.0
O2—N2—C4—C3	−1.8 (4)	C7—C6—C11—C10	0.0
O3—N2—C4—C3	178.7 (3)	C10—C11—C12—C13	0.0
C1—N1—C5—C4	−0.1 (5)	C6—C11—C12—C13	180.0
C3—C4—C5—N1	1.3 (5)	C11—C12—C13—C14	0.0
N2—C4—C5—N1	−177.6 (3)	C12—C13—C14—C15	0.0
C11—C6—C7—C8	0.0	C13—C14—C15—C10	0.0
C11—C6—C7—O1	175.81 (15)	C9—C10—C15—C14	180.0
C1—O1—C7—C6	90.0 (3)	C11—C10—C15—C14	0.0