organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-Nitro­phenyl 2-methyl­benzoate

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 17 October 2009; accepted 2 November 2009; online 7 November 2009)

The title compound, C14H11NO4, crystallizes with two mol­ecules in the asymmetric unit. The major conformational difference between these two mol­ecules is the dihedral angle between the aromatic rings, namely 36.99 (5) and 55.04 (5)°. The nitro groups are coplanar with the phenyl rings to which they are attached, the O—N—C—C torsion angles being −1.9 (3) and 1.0 (3)° in the two mol­ecules.

Related literature

For background to the applications of aromatic esters containing nitro groups in their aromatic rings, see: Jefford & Zaslona (1985[Jefford, C. W. & Zaslona, A. (1985). Tetrahedron Lett. 26, 6035-6038.]); Jefford et al. (1986[Jefford, C. W., Kubota, T. & Zaslona, A. (1986). Helv. Chim. Acta, 69, 2048-2061.]); Schauble et al. (1971[Schauble, J. H., Freed, E. H. & Swerdloff, M. D. (1971). J. Org. Chem. 36, 1302-1305.]). For related structures, see: Adams & Morsi (1976[Adams, J. M. & Morsi, S. E. (1976). Acta Cryst. B32, 1345-1347.]); Shibakami & Sekiya (1995[Shibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326-330.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11NO4

  • Mr = 257.24

  • Orthorhombic, P 21 21 21

  • a = 11.4748 (7) Å

  • b = 14.3608 (8) Å

  • c = 14.5944 (9) Å

  • V = 2405.0 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 173 K

  • 0.48 × 0.43 × 0.42 mm

Data collection
  • Stoe IPDS II two-circle diffractometer

  • Absorption correction: none

  • 8396 measured reflections

  • 2536 independent reflections

  • 2233 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.081

  • S = 1.00

  • 2536 reflections

  • 346 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Aromatic esters containing nitro groups in their aromatic rings are potential precursors for the preparation of compounds with a number of biological activities such as analgesic and anti-inflammatory (Jefford & Zaslona, 1985). In addition, these compounds served as potential intermediates in the synthesis of many natural products (Jefford et al., 1986; Schauble et al., 1971). The nitro group can be reduced to amino group which can be utilized for the synthesis of azoxy compounds. We have synthsized the title compound (I) which is a nitro substituted ester. In this article, the crystal structure of (I) is reported.

The title compound crystallizes with two molecules (Fig. 1) in an asymmetric unit. The major conformational difference between the two molecules is the dihedral angle between the aromatic rings, namely 36.99 (5)° and 55.04 (5)°. The nitro groups in both molecules are coplanar with the phenyl rings to which they are attached with dihedral angles O3—N1—C5—C6 and O3A—N1A—C5A—C4A being -1.9 (3) and 1.0 (3)°, respectively. The bond distances and angles in (I) agree well with the corresponding distances and angles reported in closely related structures (Adams & Morsi, 1976; Shibakami & Sekiya, 1995).

Related literature top

For background to the applications of aromatic esters containing nitro groups in their aromatic rings, see: Jefford & Zaslona (1985); Jefford et al. (1986); Schauble et al. (1971). For related structures, see: Adams & Morsi (1976); Shibakami & Sekiya (1995).

Experimental top

2-Toluic acid (1.5 g, 1 mol) in a 100 ml two neck round bottom flask was gradually warmed on a water bath to 323 K. Dry thionyl chloride was added in excess slowly with stirring along with 2–3 drops of DMF as catalyst. The mixture was refluxed for about 50–60 minutes at 343 K. The excess of thionyl chloride was removed by repeated evaporation at reduced pressure. In a separate flask, 4-nitrophenol (1.5 g, 0.0065 mol) was dissolved in dry dichloromethane to which triethyl amine was added at room temperature to get transparent solution. The acid chloride was added into it drop wise with constant stirring at room temperature for 30 minutes under anhydrous condition and then poured into 20 ml of cold water. Excess of triethyl amine was removed by adding cold dilute HCl solution. The reaction was monitored by TLC using ethyl acetate: n-hexane (1:2). 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), washed with 5% NaHCO3 solution and dried over anhydrous Na2SO4. After filtration the solution was concentrated to obtain the title compound which was recrystallized from n-hexane (Yield: 37 %; m.p. 336-344 K).

Refinement top

H atoms were positioned geometrically and refined using a riding model with with C—H distances 0.95 and 0.98 Å for aromatic and methyl H-atoms, respectively, and displacement parameters, Uiso = 1.2 and 1.5 times Ueq of aromatic and methyl C-atoms, respectively. The methyl groups were allowed to rotate but not to tip. Due to the absence of anomalous scatterers, the absolute structure could not be determined which was set arbitrarily and Friedel pairs (1929) were merged.

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
[Figure 1] Fig. 1. Molecular structure of the independent molecule of the title compound with displacement parameters drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular structure of the other independent molecule of the title compound with displacement parameters drawn at the 50% probability level.
4-Nitrophenyl 2-methylbenzoate top
Crystal data top
C14H11NO4F(000) = 1072
Mr = 257.24Dx = 1.421 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7991 reflections
a = 11.4748 (7) Åθ = 3.4–25.9°
b = 14.3608 (8) ŵ = 0.11 mm1
c = 14.5944 (9) ÅT = 173 K
V = 2405.0 (2) Å3Block, colourless
Z = 80.48 × 0.43 × 0.42 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
2233 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 25.6°, θmin = 3.4°
ω scansh = 1311
8396 measured reflectionsk = 1716
2536 independent reflectionsl = 1715
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0582P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2536 reflectionsΔρmax = 0.19 e Å3
346 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0029 (6)
Crystal data top
C14H11NO4V = 2405.0 (2) Å3
Mr = 257.24Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 11.4748 (7) ŵ = 0.11 mm1
b = 14.3608 (8) ÅT = 173 K
c = 14.5944 (9) Å0.48 × 0.43 × 0.42 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
2233 reflections with I > 2σ(I)
8396 measured reflectionsRint = 0.032
2536 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.081H-atom parameters constrained
S = 1.00Δρmax = 0.19 e Å3
2536 reflectionsΔρmin = 0.16 e Å3
346 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.16002 (13)0.61145 (10)0.13451 (12)0.0313 (4)
O20.01252 (14)0.62719 (11)0.06228 (12)0.0350 (4)
O30.20623 (17)0.17957 (12)0.15433 (18)0.0603 (6)
O40.04224 (17)0.19478 (12)0.22316 (14)0.0484 (5)
N10.12619 (18)0.22748 (13)0.18336 (14)0.0330 (5)
C10.07279 (19)0.66283 (14)0.09413 (15)0.0252 (4)
C20.14470 (18)0.51564 (14)0.14478 (14)0.0257 (5)
C30.0478 (2)0.47887 (15)0.18780 (15)0.0279 (5)
H30.01340.51840.20810.033*
C40.04139 (19)0.38314 (15)0.20091 (15)0.0269 (5)
H40.02420.35590.23030.032*
C50.13290 (19)0.32834 (15)0.17014 (15)0.0262 (5)
C60.23122 (19)0.36492 (15)0.12783 (15)0.0276 (5)
H60.29290.32570.10800.033*
C70.23633 (19)0.46020 (15)0.11547 (15)0.0276 (5)
H70.30240.48760.08700.033*
C110.10142 (19)0.76401 (15)0.09643 (15)0.0257 (4)
C120.0246 (2)0.82974 (15)0.05781 (15)0.0289 (5)
C130.0559 (2)0.92345 (16)0.06402 (16)0.0356 (5)
H130.00540.96920.03890.043*
C140.1581 (3)0.95161 (16)0.10555 (17)0.0398 (6)
H140.17671.01600.10880.048*
C150.2334 (2)0.88691 (17)0.14233 (17)0.0389 (6)
H150.30430.90620.17010.047*
C160.2045 (2)0.79333 (16)0.13842 (16)0.0319 (5)
H160.25540.74850.16460.038*
C170.0882 (2)0.80479 (18)0.01122 (19)0.0397 (6)
H17A0.14380.78150.05680.059*
H17B0.07380.75640.03480.059*
H17C0.12050.86020.01870.059*
O1A0.17914 (14)0.15192 (10)0.86948 (12)0.0341 (4)
O2A0.02001 (17)0.18630 (13)0.95339 (14)0.0502 (5)
O3A0.00192 (18)0.24935 (12)0.77876 (14)0.0505 (5)
O4A0.16863 (19)0.28107 (13)0.83276 (17)0.0582 (6)
N1A0.09144 (18)0.22567 (13)0.81235 (14)0.0338 (5)
C1A0.1056 (2)0.21228 (16)0.91421 (16)0.0323 (5)
C2A0.15008 (19)0.05831 (15)0.86021 (15)0.0275 (5)
C3A0.0438 (2)0.03078 (15)0.82310 (16)0.0290 (5)
H3A0.01430.07550.80860.035*
C4A0.0245 (2)0.06321 (15)0.80779 (14)0.0290 (5)
H4A0.04750.08420.78310.035*
C5A0.1119 (2)0.12599 (15)0.82913 (15)0.0273 (5)
C6A0.2179 (2)0.09892 (16)0.86513 (16)0.0309 (5)
H6A0.27640.14360.87880.037*
C7A0.23671 (19)0.00483 (17)0.88083 (16)0.0301 (5)
H7A0.30870.01590.90560.036*
C11A0.1498 (2)0.30931 (16)0.90502 (15)0.0314 (5)
C12A0.0759 (2)0.38603 (17)0.91703 (16)0.0358 (5)
C13A0.1220 (2)0.47552 (17)0.90166 (17)0.0393 (6)
H13A0.07270.52830.90760.047*
C14A0.2374 (3)0.48793 (17)0.87809 (18)0.0417 (6)
H14A0.26640.54900.86800.050*
C15A0.3114 (2)0.41263 (18)0.86902 (18)0.0418 (6)
H15A0.39130.42180.85450.050*
C16A0.2678 (2)0.32367 (16)0.88133 (16)0.0362 (5)
H16A0.31790.27160.87380.043*
C17A0.0493 (2)0.3775 (2)0.9429 (2)0.0478 (7)
H17D0.08910.33660.89920.072*
H17E0.08580.43920.94180.072*
H17F0.05550.35121.00460.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0282 (8)0.0198 (7)0.0458 (9)0.0024 (6)0.0051 (7)0.0052 (7)
O20.0326 (9)0.0235 (7)0.0490 (10)0.0024 (7)0.0090 (7)0.0003 (7)
O30.0469 (11)0.0246 (9)0.1094 (18)0.0035 (9)0.0207 (12)0.0050 (10)
O40.0533 (12)0.0290 (9)0.0628 (12)0.0075 (9)0.0194 (10)0.0070 (8)
N10.0342 (11)0.0216 (9)0.0431 (11)0.0006 (9)0.0008 (9)0.0007 (8)
C10.0267 (11)0.0211 (10)0.0277 (10)0.0031 (9)0.0032 (9)0.0001 (9)
C20.0270 (11)0.0202 (10)0.0299 (11)0.0019 (9)0.0037 (9)0.0019 (8)
C30.0263 (11)0.0256 (11)0.0318 (12)0.0024 (9)0.0033 (9)0.0006 (8)
C40.0267 (11)0.0235 (10)0.0305 (11)0.0003 (9)0.0020 (9)0.0016 (8)
C50.0285 (11)0.0213 (10)0.0289 (10)0.0010 (9)0.0008 (9)0.0006 (8)
C60.0240 (10)0.0279 (11)0.0310 (11)0.0027 (9)0.0012 (9)0.0005 (9)
C70.0229 (10)0.0285 (11)0.0313 (11)0.0021 (9)0.0014 (9)0.0042 (9)
C110.0305 (11)0.0210 (10)0.0256 (10)0.0011 (9)0.0058 (9)0.0006 (8)
C120.0322 (12)0.0264 (11)0.0280 (11)0.0026 (9)0.0084 (9)0.0028 (8)
C130.0474 (14)0.0240 (11)0.0353 (13)0.0028 (11)0.0123 (11)0.0033 (9)
C140.0614 (17)0.0225 (11)0.0356 (12)0.0074 (11)0.0124 (12)0.0028 (10)
C150.0490 (15)0.0339 (13)0.0339 (12)0.0134 (12)0.0030 (11)0.0048 (10)
C160.0349 (12)0.0284 (11)0.0326 (12)0.0034 (10)0.0008 (10)0.0029 (9)
C170.0353 (13)0.0329 (13)0.0508 (15)0.0036 (11)0.0013 (11)0.0137 (11)
O1A0.0339 (8)0.0227 (8)0.0458 (9)0.0038 (7)0.0081 (8)0.0041 (7)
O2A0.0481 (11)0.0414 (10)0.0612 (12)0.0108 (9)0.0244 (10)0.0146 (9)
O3A0.0573 (12)0.0319 (9)0.0624 (13)0.0084 (9)0.0172 (10)0.0089 (8)
O4A0.0563 (12)0.0258 (9)0.0926 (16)0.0109 (9)0.0109 (11)0.0031 (10)
N1A0.0404 (11)0.0262 (10)0.0349 (11)0.0008 (9)0.0004 (9)0.0034 (8)
C1A0.0328 (12)0.0315 (12)0.0326 (12)0.0001 (10)0.0041 (10)0.0022 (10)
C2A0.0303 (11)0.0239 (10)0.0283 (10)0.0027 (9)0.0064 (10)0.0003 (9)
C3A0.0275 (11)0.0262 (10)0.0332 (11)0.0046 (9)0.0006 (10)0.0028 (9)
C4A0.0290 (11)0.0294 (11)0.0285 (11)0.0016 (10)0.0027 (9)0.0014 (9)
C5A0.0318 (11)0.0234 (10)0.0267 (10)0.0005 (9)0.0010 (9)0.0014 (8)
C6A0.0290 (11)0.0276 (11)0.0361 (12)0.0047 (9)0.0004 (10)0.0001 (10)
C7A0.0242 (10)0.0320 (11)0.0343 (12)0.0011 (9)0.0011 (9)0.0017 (9)
C11A0.0400 (13)0.0285 (11)0.0257 (10)0.0009 (10)0.0022 (10)0.0048 (9)
C12A0.0410 (13)0.0358 (13)0.0307 (12)0.0030 (11)0.0060 (10)0.0087 (10)
C13A0.0528 (15)0.0317 (12)0.0334 (12)0.0020 (11)0.0113 (12)0.0079 (10)
C14A0.0594 (16)0.0283 (13)0.0374 (13)0.0031 (12)0.0043 (12)0.0024 (10)
C15A0.0449 (14)0.0360 (13)0.0446 (14)0.0087 (12)0.0046 (12)0.0023 (11)
C16A0.0451 (14)0.0268 (12)0.0366 (13)0.0042 (11)0.0013 (11)0.0005 (9)
C17A0.0438 (15)0.0465 (15)0.0532 (16)0.0061 (13)0.0041 (13)0.0124 (12)
Geometric parameters (Å, º) top
O1—C11.376 (3)O1A—C1A1.375 (3)
O1—C21.395 (2)O1A—C2A1.392 (3)
O2—C11.199 (3)O2A—C1A1.196 (3)
O3—N11.223 (3)O3A—N1A1.226 (3)
O4—N11.219 (3)O4A—N1A1.227 (3)
N1—C51.463 (3)N1A—C5A1.471 (3)
C1—C111.490 (3)C1A—C11A1.489 (3)
C2—C31.382 (3)C2A—C7A1.379 (3)
C2—C71.387 (3)C2A—C3A1.392 (3)
C3—C41.390 (3)C3A—C4A1.386 (3)
C3—H30.9500C3A—H3A0.9500
C4—C51.387 (3)C4A—C5A1.384 (3)
C4—H40.9500C4A—H4A0.9500
C5—C61.389 (3)C5A—C6A1.381 (3)
C6—C71.381 (3)C6A—C7A1.387 (3)
C6—H60.9500C6A—H6A0.9500
C7—H70.9500C7A—H7A0.9500
C11—C161.397 (3)C11A—C12A1.401 (3)
C11—C121.409 (3)C11A—C16A1.412 (4)
C12—C131.396 (3)C12A—C13A1.408 (4)
C12—C171.505 (3)C12A—C17A1.491 (4)
C13—C141.381 (4)C13A—C14A1.380 (4)
C13—H130.9500C13A—H13A0.9500
C14—C151.377 (4)C14A—C15A1.381 (4)
C14—H140.9500C14A—H14A0.9500
C15—C161.385 (3)C15A—C16A1.384 (4)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
C17—H17A0.9800C17A—H17D0.9800
C17—H17B0.9800C17A—H17E0.9800
C17—H17C0.9800C17A—H17F0.9800
C1—O1—C2118.90 (16)C1A—O1A—C2A120.55 (18)
O4—N1—O3122.80 (19)O3A—N1A—O4A123.2 (2)
O4—N1—C5119.06 (19)O3A—N1A—C5A118.4 (2)
O3—N1—C5118.1 (2)O4A—N1A—C5A118.4 (2)
O2—C1—O1122.09 (18)O2A—C1A—O1A122.3 (2)
O2—C1—C11127.2 (2)O2A—C1A—C11A127.9 (2)
O1—C1—C11110.67 (18)O1A—C1A—C11A109.76 (19)
C3—C2—C7122.06 (19)C7A—C2A—C3A122.0 (2)
C3—C2—O1121.81 (19)C7A—C2A—O1A116.19 (19)
C7—C2—O1115.96 (19)C3A—C2A—O1A121.5 (2)
C2—C3—C4118.9 (2)C4A—C3A—C2A118.7 (2)
C2—C3—H3120.5C4A—C3A—H3A120.7
C4—C3—H3120.5C2A—C3A—H3A120.7
C5—C4—C3118.5 (2)C5A—C4A—C3A118.8 (2)
C5—C4—H4120.8C5A—C4A—H4A120.6
C3—C4—H4120.8C3A—C4A—H4A120.6
C4—C5—C6123.0 (2)C6A—C5A—C4A122.7 (2)
C4—C5—N1118.6 (2)C6A—C5A—N1A118.5 (2)
C6—C5—N1118.4 (2)C4A—C5A—N1A118.7 (2)
C7—C6—C5117.8 (2)C5A—C6A—C7A118.3 (2)
C7—C6—H6121.1C5A—C6A—H6A120.8
C5—C6—H6121.1C7A—C6A—H6A120.8
C6—C7—C2119.8 (2)C2A—C7A—C6A119.5 (2)
C6—C7—H7120.1C2A—C7A—H7A120.3
C2—C7—H7120.1C6A—C7A—H7A120.3
C16—C11—C12120.2 (2)C12A—C11A—C16A119.7 (2)
C16—C11—C1119.4 (2)C12A—C11A—C1A121.2 (2)
C12—C11—C1120.4 (2)C16A—C11A—C1A119.0 (2)
C13—C12—C11117.3 (2)C11A—C12A—C13A118.1 (2)
C13—C12—C17118.7 (2)C11A—C12A—C17A123.4 (2)
C11—C12—C17124.0 (2)C13A—C12A—C17A118.5 (2)
C14—C13—C12122.0 (2)C14A—C13A—C12A121.2 (2)
C14—C13—H13119.0C14A—C13A—H13A119.4
C12—C13—H13119.0C12A—C13A—H13A119.4
C15—C14—C13120.4 (2)C13A—C14A—C15A120.8 (2)
C15—C14—H14119.8C13A—C14A—H14A119.6
C13—C14—H14119.8C15A—C14A—H14A119.6
C14—C15—C16119.2 (2)C14A—C15A—C16A119.2 (2)
C14—C15—H15120.4C14A—C15A—H15A120.4
C16—C15—H15120.4C16A—C15A—H15A120.4
C15—C16—C11120.9 (2)C15A—C16A—C11A120.9 (2)
C15—C16—H16119.6C15A—C16A—H16A119.6
C11—C16—H16119.6C11A—C16A—H16A119.6
C12—C17—H17A109.5C12A—C17A—H17D109.5
C12—C17—H17B109.5C12A—C17A—H17E109.5
H17A—C17—H17B109.5H17D—C17A—H17E109.5
C12—C17—H17C109.5C12A—C17A—H17F109.5
H17A—C17—H17C109.5H17D—C17A—H17F109.5
H17B—C17—H17C109.5H17E—C17A—H17F109.5
C2—O1—C1—O24.9 (3)C2A—O1A—C1A—O2A6.6 (4)
C2—O1—C1—C11175.37 (18)C2A—O1A—C1A—C11A173.3 (2)
C1—O1—C2—C353.7 (3)C1A—O1A—C2A—C7A133.2 (2)
C1—O1—C2—C7130.9 (2)C1A—O1A—C2A—C3A53.3 (3)
C7—C2—C3—C40.9 (3)C7A—C2A—C3A—C4A0.9 (3)
O1—C2—C3—C4176.0 (2)O1A—C2A—C3A—C4A174.1 (2)
C2—C3—C4—C50.0 (3)C2A—C3A—C4A—C5A0.6 (3)
C3—C4—C5—C60.8 (3)C3A—C4A—C5A—C6A0.0 (3)
C3—C4—C5—N1179.7 (2)C3A—C4A—C5A—N1A179.7 (2)
O4—N1—C5—C42.0 (3)O3A—N1A—C5A—C6A178.6 (2)
O3—N1—C5—C4178.5 (2)O4A—N1A—C5A—C6A1.4 (3)
O4—N1—C5—C6177.5 (2)O3A—N1A—C5A—C4A1.0 (3)
O3—N1—C5—C61.9 (3)O4A—N1A—C5A—C4A178.9 (2)
C4—C5—C6—C70.7 (3)C4A—C5A—C6A—C7A0.3 (3)
N1—C5—C6—C7179.8 (2)N1A—C5A—C6A—C7A180.0 (2)
C5—C6—C7—C20.2 (3)C3A—C2A—C7A—C6A0.6 (4)
C3—C2—C7—C61.0 (3)O1A—C2A—C7A—C6A174.1 (2)
O1—C2—C7—C6176.4 (2)C5A—C6A—C7A—C2A0.1 (4)
O2—C1—C11—C16178.7 (2)O2A—C1A—C11A—C12A20.9 (4)
O1—C1—C11—C161.6 (3)O1A—C1A—C11A—C12A159.0 (2)
O2—C1—C11—C120.4 (4)O2A—C1A—C11A—C16A160.8 (3)
O1—C1—C11—C12179.30 (19)O1A—C1A—C11A—C16A19.3 (3)
C16—C11—C12—C130.3 (3)C16A—C11A—C12A—C13A2.2 (3)
C1—C11—C12—C13178.79 (19)C1A—C11A—C12A—C13A176.1 (2)
C16—C11—C12—C17180.0 (2)C16A—C11A—C12A—C17A179.4 (2)
C1—C11—C12—C170.9 (3)C1A—C11A—C12A—C17A2.3 (4)
C11—C12—C13—C140.4 (3)C11A—C12A—C13A—C14A1.9 (4)
C17—C12—C13—C14179.8 (2)C17A—C12A—C13A—C14A179.6 (2)
C12—C13—C14—C150.2 (4)C12A—C13A—C14A—C15A0.1 (4)
C13—C14—C15—C161.0 (4)C13A—C14A—C15A—C16A1.8 (4)
C14—C15—C16—C111.1 (4)C14A—C15A—C16A—C11A1.5 (4)
C12—C11—C16—C150.4 (3)C12A—C11A—C16A—C15A0.5 (4)
C1—C11—C16—C15179.6 (2)C1A—C11A—C16A—C15A177.8 (2)

Experimental details

Crystal data
Chemical formulaC14H11NO4
Mr257.24
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)11.4748 (7), 14.3608 (8), 14.5944 (9)
V3)2405.0 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.48 × 0.43 × 0.42
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8396, 2536, 2233
Rint0.032
(sin θ/λ)max1)0.607
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.081, 1.00
No. of reflections2536
No. of parameters346
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.16

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

 

Acknowledgements

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

References

First citationAdams, J. M. & Morsi, S. E. (1976). Acta Cryst. B32, 1345–1347.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationJefford, C. W., Kubota, T. & Zaslona, A. (1986). Helv. Chim. Acta, 69, 2048–2061.  CrossRef CAS Web of Science Google Scholar
First citationJefford, C. W. & Zaslona, A. (1985). Tetrahedron Lett. 26, 6035–6038.  CrossRef CAS Web of Science Google Scholar
First citationSchauble, J. H., Freed, E. H. & Swerdloff, M. D. (1971). J. Org. Chem. 36, 1302–1305.  CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326–330.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationStoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds