4-Nitro­phenyl 1-naphthoate

Bibi, U.; Siddiqi, H.M.; Akhter, Z.; Bolte, M.

doi:10.1107/S1600536810011736

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1023

https://doi.org/10.1107/S1600536810011736

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4-Nitrophenyl 1-naphthoate

Uzma Bibi,^a Humaira M. Siddiqi,^a ^* Zareen Akhter ^a and Michael Bolte ^b

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische Chemie, J.-W.-Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: humaira_siddiqi@yahoo.com

(Received 27 March 2010; accepted 29 March 2010; online 2 April 2010)

In the title compound, C₁₇H₁₁NO₄, 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 intermolecular 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_r = 293.27
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.088
S = 0.96
2508 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810011736/tk2650Isup2.hkl

checkCIF report

Comment top

The ability of non-steroidal anti–inflammatory drugs (NSAID's) to modulate the pain, inflammation and fever make them attractive drugs (Bezerra-Netto et al., 2006). Aromatic esters containing a nitro-substituted phenyl ring form a medicinally important class of NSAID's. These can be used as starting materials for the preparation of several analgesic and anti–inflammatory drugs, and some of them are potential intermediates in natural product syntheses (Selvakumar et al., 2002). Nitro compounds can be reduced to give amines which are important synthons for preparing a large number of technologically important materials (Kumarraja et al., 2004; Tafesh et al., 1996). In continuation of studies on related compounds (Bibi et al., 2009), the title compound is reported herein.

A perspective view of the title compound is shown in Fig. 1. The dihedral angle formed between the two aromatic ring systems is 8.66 (3)°. The nitro group is twisted by only 4.51 (9)° out of the plane of the aromatic ring to which it is attached. The crystal structure is stabilized by C—H···O contacts, Table 1.

Related literature top

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 top

1-Naphthoic acid (1.5 g, 1 mol) was taken in a 100 ml two neck round bottom flask and warmed on a water bath to 323 K. An excess of dry thionyl chloride was added slowly with stirring. Drops (2-3) of DMF were added and the mixture was refluxed for about 50-60 minutes at 343 K. After the completion of the reaction, excess thionyl chloride was removed by repeated evaporations at reduced pressure. 4-Nitrophenol (1.5 g, 0.0065 mol) was dissolved in dry dichloromethane containing triethyl amine at room temperature. The acid chloride was added drop-wise with constant stirring at room temperature for half an hour. The reaction mixture was heated gently for 30 minutes under anhydrous condition and then the solution was poured with constant stirring into cold water (20 ml ). Excess triethyl amine was destroyed by adding the cold dilute HCl solution. The reaction was monitored by TLC using ethyl acetate:n-hexane (1:1). After the completion of reaction the oily product was allowed to settle down and the supernatant liquid was decanted. The product was stirred well with distilled water and extracted with ethyl acetate (3 x 40 ml). Washing was done with 5% NaHCO₃ solution to remove unreacted acid and the extract was dried over anhydrous Na₂SO₄, filtered, and concentrated on a rotary evaporator. The ester soon solidified and was filtered. The title compound was recrystallized from n-hexane (Yield 36.5 %, m.pt. 385–393 K)

Structure description top

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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

4-Nitrophenyl 1-naphthoate top

Crystal data top

C₁₇H₁₁NO₄	F(000) = 608
M_r = 293.27	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0582P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
2508 reflections	Δρ_max = 0.26 e Å⁻³
200 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₁₁NO₄	V = 1348.44 (19) Å³
M_r = 293.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2049 (6) Å	µ = 0.10 mm⁻¹
b = 12.8175 (8) Å	T = 173 K
c = 14.7838 (14) Å	0.25 × 0.21 × 0.21 mm
β = 99.006 (7)°

Data collection top

Stoe IPDS-II two-circle diffractometer	1928 reflections with I > 2σ(I)
10239 measured reflections	R_int = 0.040
2508 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 0.96	Δρ_max = 0.26 e Å⁻³
2508 reflections	Δρ_min = −0.20 e Å⁻³
200 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁NO₄
M_r	293.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.2049 (6), 12.8175 (8), 14.7838 (14)
β (°)	99.006 (7)
V (Å³)	1348.44 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.21 × 0.21

Data collection
Diffractometer	Stoe IPDS-II two-circle
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10239, 2508, 1928
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.088, 0.96
No. of reflections	2508
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.20

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.9500	2.4500	3.3728 (18)	164.00

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The authors are grateful to the University Research Fund 2008–09, Department of Chemistry, Quaid-I-Azam University, for support. The Institut für Anorganische Chemie, J.-W.-Goethe-Universität Frankfurt, is acknowledged for providing laboratory and analytical facilities.

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