4-Nitro-phenyl 1-naphthoate.

In the title compound, C(17)H(11)NO(4), the dihedral angle between the two benzene rings is 8.66 (3)°. The nitro group is twisted by 4.51 (9)° out of the plane of the aromatic ring to which it is attached. The presence of inter-molecular C-H⋯O contacts in the crystal structure leads to the formation of chains along the c axis.

Related literature

For biological and synthetic background, see: Bezerra-Netto et al. (2006 ▶); Bibi et al. (2009 ▶); Kumarraja & Pitchumani (2004 ▶); Selvakumar et al. (2002 ▶); Tafesh & Weiguny (1996 ▶).

Experimental

Crystal data

C17H11NO4

M = 293.27

Monoclinic,

a = 7.2049 (6) Å

b = 12.8175 (8) Å

c = 14.7838 (14) Å

β = 99.006 (7)°

V = 1348.44 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.25 × 0.21 × 0.21 mm

Data collection

Stoe IPDS-II two-circle diffractometer

10239 measured reflections

2508 independent reflections

1928 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 0.96

2508 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011736/tk2650sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011736/tk2650Isup2.hkl

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

C17H11NO4	F(000) = 608
Mr = 293.27	Dx = 1.445 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8709 reflections
a = 7.2049 (6) Å	θ = 3.3–26.0°
b = 12.8175 (8) Å	µ = 0.10 mm−1
c = 14.7838 (14) Å	T = 173 K
β = 99.006 (7)°	Block, colourless
V = 1348.44 (19) Å3	0.25 × 0.21 × 0.21 mm
Z = 4

Stoe IPDS-II two-circle diffractometer	1928 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
graphite	θmax = 25.6°, θmin = 3.3°
ω scans	h = −8→8
10239 measured reflections	k = −15→15
2508 independent reflections	l = −13→17

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0582P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
2508 reflections	Δρmax = 0.26 e Å−3
200 parameters	Δρmin = −0.20 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: 0.0103 (16)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1	0.36959 (17)	0.15975 (9)	0.73346 (9)	0.0357 (3)
O1	0.28241 (13)	0.47946 (6)	0.47417 (6)	0.0264 (2)
O2	0.14518 (13)	0.59160 (7)	0.56191 (7)	0.0303 (2)
O3	0.42873 (18)	0.18063 (9)	0.81407 (8)	0.0526 (3)
O4	0.33027 (18)	0.07066 (8)	0.70625 (9)	0.0519 (3)
C1	0.19783 (17)	0.57191 (9)	0.49057 (9)	0.0239 (3)
C2	0.30357 (17)	0.40273 (9)	0.54233 (9)	0.0239 (3)
C3	0.38432 (18)	0.42424 (10)	0.63163 (10)	0.0275 (3)
H3	0.4249	0.4929	0.6491	0.033*
C4	0.40489 (18)	0.34404 (10)	0.69505 (10)	0.0291 (3)
H4	0.4579	0.3568	0.7570	0.035*
C5	0.34691 (18)	0.24492 (10)	0.66653 (9)	0.0272 (3)
C6	0.27048 (19)	0.22251 (10)	0.57696 (10)	0.0301 (3)
H6	0.2335	0.1534	0.5592	0.036*
C7	0.24893 (19)	0.30293 (10)	0.51368 (10)	0.0280 (3)
H7	0.1975	0.2899	0.4516	0.034*
C11	0.17730 (17)	0.63938 (10)	0.40772 (9)	0.0239 (3)
C12	0.20200 (17)	0.75036 (9)	0.41572 (9)	0.0250 (3)
C13	0.2570 (2)	0.80306 (10)	0.49996 (10)	0.0323 (3)
H13	0.2770	0.7646	0.5556	0.039*
C14	0.2816 (2)	0.90913 (11)	0.50176 (12)	0.0426 (4)
H14	0.3169	0.9436	0.5588	0.051*
C15	0.2553 (2)	0.96756 (11)	0.42033 (13)	0.0460 (4)
H15	0.2738	1.0410	0.4226	0.055*
C16	0.2035 (2)	0.91929 (11)	0.33809 (12)	0.0380 (4)
H16	0.1867	0.9594	0.2834	0.046*
C17	0.17434 (18)	0.80981 (10)	0.33332 (10)	0.0286 (3)
C18	0.12013 (19)	0.75958 (11)	0.24776 (10)	0.0322 (3)
H18	0.0998	0.8000	0.1932	0.039*
C19	0.0969 (2)	0.65407 (11)	0.24282 (10)	0.0334 (3)
H19	0.0601	0.6213	0.1851	0.040*
C20	0.12749 (19)	0.59370 (10)	0.32339 (10)	0.0288 (3)
H20	0.1134	0.5201	0.3193	0.035*

	U11	U22	U33	U12	U13	U23
N1	0.0365 (7)	0.0352 (7)	0.0361 (8)	0.0029 (5)	0.0078 (5)	0.0115 (5)
O1	0.0335 (5)	0.0227 (4)	0.0240 (5)	0.0043 (4)	0.0081 (4)	0.0044 (4)
O2	0.0387 (6)	0.0295 (5)	0.0240 (5)	0.0049 (4)	0.0089 (4)	0.0020 (4)
O3	0.0747 (9)	0.0495 (7)	0.0318 (7)	0.0025 (6)	0.0026 (6)	0.0140 (5)
O4	0.0705 (8)	0.0296 (6)	0.0539 (8)	−0.0058 (5)	0.0045 (6)	0.0137 (5)
C1	0.0237 (6)	0.0228 (6)	0.0251 (7)	−0.0011 (5)	0.0036 (5)	−0.0006 (5)
C2	0.0236 (6)	0.0241 (6)	0.0252 (7)	0.0031 (5)	0.0075 (5)	0.0043 (5)
C3	0.0278 (7)	0.0253 (6)	0.0289 (8)	−0.0011 (5)	0.0033 (5)	0.0004 (5)
C4	0.0277 (7)	0.0333 (7)	0.0256 (8)	0.0022 (5)	0.0018 (6)	0.0022 (6)
C5	0.0253 (7)	0.0280 (7)	0.0291 (8)	0.0039 (5)	0.0070 (5)	0.0090 (5)
C6	0.0316 (7)	0.0233 (6)	0.0350 (9)	0.0002 (5)	0.0045 (6)	0.0016 (6)
C7	0.0303 (7)	0.0275 (7)	0.0256 (7)	0.0026 (5)	0.0026 (5)	−0.0007 (5)
C11	0.0219 (6)	0.0259 (6)	0.0246 (7)	0.0012 (5)	0.0053 (5)	0.0029 (5)
C12	0.0218 (6)	0.0254 (6)	0.0282 (8)	0.0015 (5)	0.0051 (5)	0.0029 (5)
C13	0.0368 (8)	0.0296 (7)	0.0299 (8)	−0.0010 (5)	0.0033 (6)	0.0004 (6)
C14	0.0546 (10)	0.0309 (8)	0.0409 (10)	−0.0040 (6)	0.0033 (7)	−0.0061 (6)
C15	0.0567 (11)	0.0247 (7)	0.0561 (12)	−0.0042 (7)	0.0070 (8)	0.0015 (7)
C16	0.0397 (8)	0.0300 (7)	0.0441 (10)	0.0021 (6)	0.0061 (7)	0.0131 (6)
C17	0.0235 (6)	0.0293 (7)	0.0333 (8)	0.0023 (5)	0.0058 (6)	0.0063 (6)
C18	0.0315 (7)	0.0386 (8)	0.0265 (8)	0.0016 (6)	0.0042 (6)	0.0111 (6)
C19	0.0372 (8)	0.0396 (8)	0.0228 (7)	−0.0025 (6)	0.0026 (6)	0.0010 (6)
C20	0.0314 (7)	0.0281 (6)	0.0271 (8)	−0.0013 (5)	0.0050 (6)	0.0009 (5)

N1—O4	1.2290 (16)	C11—C12	1.4362 (18)
N1—O3	1.2307 (18)	C12—C13	1.418 (2)
N1—C5	1.4651 (17)	C12—C17	1.4242 (19)
O1—C1	1.3713 (15)	C13—C14	1.371 (2)
O1—C2	1.3993 (15)	C13—H13	0.9500
O2—C1	1.2022 (17)	C14—C15	1.405 (2)
C1—C11	1.4876 (18)	C14—H14	0.9500
C2—C3	1.385 (2)	C15—C16	1.363 (2)
C2—C7	1.3850 (18)	C15—H15	0.9500
C3—C4	1.3836 (19)	C16—C17	1.4191 (19)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.3825 (19)	C17—C18	1.419 (2)
C4—H4	0.9500	C18—C19	1.363 (2)
C5—C6	1.382 (2)	C18—H18	0.9500
C6—C7	1.3844 (19)	C19—C20	1.409 (2)
C6—H6	0.9500	C19—H19	0.9500
C7—H7	0.9500	C20—H20	0.9500
C11—C20	1.373 (2)
O4—N1—O3	123.10 (12)	C13—C12—C17	118.61 (12)
O4—N1—C5	118.41 (13)	C13—C12—C11	123.94 (12)
O3—N1—C5	118.49 (12)	C17—C12—C11	117.43 (12)
C1—O1—C2	118.78 (10)	C14—C13—C12	120.47 (14)
O2—C1—O1	123.12 (12)	C14—C13—H13	119.8
O2—C1—C11	126.58 (11)	C12—C13—H13	119.8
O1—C1—C11	110.27 (11)	C13—C14—C15	120.82 (15)
C3—C2—C7	122.17 (12)	C13—C14—H14	119.6
C3—C2—O1	121.92 (11)	C15—C14—H14	119.6
C7—C2—O1	115.80 (12)	C16—C15—C14	120.24 (14)
C4—C3—C2	118.86 (12)	C16—C15—H15	119.9
C4—C3—H3	120.6	C14—C15—H15	119.9
C2—C3—H3	120.6	C15—C16—C17	120.72 (14)
C5—C4—C3	118.75 (13)	C15—C16—H16	119.6
C5—C4—H4	120.6	C17—C16—H16	119.6
C3—C4—H4	120.6	C18—C17—C16	120.73 (13)
C4—C5—C6	122.62 (12)	C18—C17—C12	120.13 (12)
C4—C5—N1	118.84 (13)	C16—C17—C12	119.13 (13)
C6—C5—N1	118.53 (12)	C19—C18—C17	120.82 (13)
C5—C6—C7	118.57 (12)	C19—C18—H18	119.6
C5—C6—H6	120.7	C17—C18—H18	119.6
C7—C6—H6	120.7	C18—C19—C20	119.87 (13)
C6—C7—C2	118.99 (13)	C18—C19—H19	120.1
C6—C7—H7	120.5	C20—C19—H19	120.1
C2—C7—H7	120.5	C11—C20—C19	121.17 (12)
C20—C11—C12	120.56 (12)	C11—C20—H20	119.4
C20—C11—C1	118.54 (11)	C19—C20—H20	119.4
C12—C11—C1	120.86 (12)
C2—O1—C1—O2	2.09 (18)	C20—C11—C12—C13	−178.63 (13)
C2—O1—C1—C11	−176.10 (10)	C1—C11—C12—C13	3.73 (19)
C1—O1—C2—C3	−51.49 (16)	C20—C11—C12—C17	−0.49 (18)
C1—O1—C2—C7	132.16 (12)	C1—C11—C12—C17	−178.13 (11)
C7—C2—C3—C4	−2.4 (2)	C17—C12—C13—C14	0.4 (2)
O1—C2—C3—C4	−178.48 (12)	C11—C12—C13—C14	178.56 (14)
C2—C3—C4—C5	1.1 (2)	C12—C13—C14—C15	−0.8 (2)
C3—C4—C5—C6	0.5 (2)	C13—C14—C15—C16	0.4 (3)
C3—C4—C5—N1	179.64 (12)	C14—C15—C16—C17	0.3 (2)
O4—N1—C5—C4	−174.87 (13)	C15—C16—C17—C18	179.92 (14)
O3—N1—C5—C4	4.5 (2)	C15—C16—C17—C12	−0.7 (2)
O4—N1—C5—C6	4.29 (19)	C13—C12—C17—C18	179.70 (12)
O3—N1—C5—C6	−176.38 (13)	C11—C12—C17—C18	1.46 (18)
C4—C5—C6—C7	−0.9 (2)	C13—C12—C17—C16	0.31 (19)
N1—C5—C6—C7	179.98 (12)	C11—C12—C17—C16	−177.93 (12)
C5—C6—C7—C2	−0.3 (2)	C16—C17—C18—C19	178.26 (14)
C3—C2—C7—C6	2.0 (2)	C12—C17—C18—C19	−1.1 (2)
O1—C2—C7—C6	178.32 (12)	C17—C18—C19—C20	−0.2 (2)
O2—C1—C11—C20	−138.43 (14)	C12—C11—C20—C19	−0.8 (2)
O1—C1—C11—C20	39.68 (15)	C1—C11—C20—C19	176.85 (12)
O2—C1—C11—C12	39.26 (19)	C18—C19—C20—C11	1.2 (2)
O1—C1—C11—C12	−142.63 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2i	0.95	2.45	3.3728 (18)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2i	0.95	2.45	3.3728 (18)	164

Symmetry code: (i) .