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The maximum deviation from the mean plane of the furobenzo­pyran­one skeleton of the title compound, C13H9NO5, indicates a reasonably planar system. The other non-H atoms are nearly coplanar with this three-ring framework. Intra- and intermolecular C—H...O hydrogen bonds are observed. The crystal packing is determined by such contacts and the mol­ecules are stacked in sheets with a spacing of 3.47 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019699/dn6010sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019699/dn6010Isup2.hkl
Contains datablock I

CCDC reference: 180539

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.069
  • wR factor = 0.168
  • Data-to-parameter ratio = 8.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
THETM_01 Alert A The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.5384
Yellow Alert Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.5384 Proportion of unique data used 1.0000 Ratio reflections to parameters 8.5058
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title compound, (I), was obtained as an intermediate in the multistage of derivatives of 4-oxo-4H-1-benzopyran-7-carboxylic acid. These derivatives show low toxicity and analgesic and anti-inflammatory activity comparable to acetylsalicylic acid (Kossakowski & Zawadowski, 1995).

Fig. 1 shows a perspective view of the molecule. The furobenzopyranone system is essentially planar with no atomic deviation greater than 0.052 (3) Å from its least-squares plane (r.m.s. deviation 0.029 Å). Both the nitro group and atoms O14, C15 and C19 are found to be insignificantly out of this plane. The deviations range from -0.134 (5) for C9 to 0.060 (5) Å for O14. All bond lengths and valence angles observed in the compound are in good agreement with the corresponding distances in the related compounds (Léger et al.,1981; Ajana et al., 1987; El-Sayed et al., 1988; Hariharan & Rajan, 1990; Ginderow, 1991; Koh & Ng, 1993). The structure is stabilized by C—H···O-type contacts and stacking forces. The molecules connected through inversion center are linked by C10—H10···O11, C7—H7···O18 and C19—H19A···O14 hydrogen bonds, forming sheets (Fig.2) along the [120] and [120] directions. The perpendicular distance between partly overlapping molecules from the neighbouring parallel sheets is 3.47 Å. Cohesion between non-parallel sheets results also in C—H···O (C3—H3···O14 and C15—H15C···O17) interactions (Fig. 3). The geometric parameters of all intra- and intermolecular hydrogen bonds are given in Table 1.

Experimental top

The synthesis of the title compound has been described elsewhere (Kossakowski & Zawadowski, 1995). Crystals were grown from acetic acid by slow evaporation.

Refinement top

The H atoms were refined as riding and their Uiso values were set at 1.2 (1.5 for methyl groups) times Ueq of their carrier atoms.

Computing details top

Data collection: CrysAlis CCD (Kuma, 1999); cell refinement: CrysAlis RED (Kuma, 1999); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation (Siemens, 1989); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the title compound together with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view showing the interconnections within a sheet. Dashed lines indicate hydrogen bonds.
[Figure 3] Fig. 3. A view showing the interconnections between sheets
2,6-Dimethyl-3-nitro-8H-furo[2,3-g][1]-benzopyran-8-one top
Crystal data top
C13H9NO5F(000) = 536
Mr = 259.21Dx = 1.531 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.111 (2) ÅCell parameters from 2228 reflections
b = 5.732 (1) Åθ = 2.5–21.2°
c = 24.235 (5) ŵ = 0.12 mm1
β = 93.51 (3)°T = 293 K
V = 1124.6 (4) Å3Prism, orange
Z = 40.6 × 0.25 × 0.03 mm
Data collection top
Kuma KM-4 CCD
diffractometer
1329 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.079
Graphite monochromatorθmax = 22.5°, θmin = 3.7°
ω/2θ scansh = 88
4062 measured reflectionsk = 46
1463 independent reflectionsl = 2624
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0628P)2 + 1.4018P]
where P = (Fo2 + 2Fc2)/3
1463 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C13H9NO5V = 1124.6 (4) Å3
Mr = 259.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.111 (2) ŵ = 0.12 mm1
b = 5.732 (1) ÅT = 293 K
c = 24.235 (5) Å0.6 × 0.25 × 0.03 mm
β = 93.51 (3)°
Data collection top
Kuma KM-4 CCD
diffractometer
1329 reflections with I > 2σ(I)
4062 measured reflectionsRint = 0.079
1463 independent reflectionsθmax = 22.5°
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.168H-atom parameters constrained
S = 1.13Δρmax = 0.28 e Å3
1463 reflectionsΔρmin = 0.28 e Å3
172 parameters
Special details top

Experimental. The data were collected up to two theta of 60°, however, those above 45° have insignificant intensity and were ignored during the refinement

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
O10.2082 (3)1.2345 (4)0.63614 (10)0.0466 (8)
C20.2591 (5)1.1733 (7)0.68872 (17)0.0498 (11)
C30.3546 (5)0.9890 (8)0.69977 (17)0.0523 (11)
H30.38820.95730.73640.063*
C40.4077 (5)0.8374 (7)0.65758 (17)0.0492 (11)
C50.3491 (5)0.9011 (6)0.60149 (15)0.0391 (10)
C60.2517 (4)1.0989 (6)0.59301 (15)0.0361 (9)
C70.1918 (4)1.1731 (6)0.54121 (15)0.0373 (9)
H70.13001.30920.53660.045*
C80.2281 (4)1.0358 (6)0.49683 (15)0.0359 (9)
C90.3241 (4)0.8369 (6)0.50553 (15)0.0356 (9)
C100.3857 (5)0.7647 (6)0.55595 (16)0.0402 (10)
H100.44950.63030.56010.048*
O110.3429 (3)0.7235 (4)0.45595 (10)0.0421 (7)
C120.2591 (5)0.8493 (6)0.41564 (16)0.0395 (10)
C130.1907 (4)1.0374 (6)0.43831 (15)0.0356 (9)
O140.4981 (4)0.6673 (6)0.66701 (13)0.0746 (11)
C150.1959 (7)1.3375 (9)0.72908 (19)0.0693 (14)
H15A0.13001.45480.71000.104*
H15B0.28701.41020.74960.104*
H15C0.12951.25450.75400.104*
N160.0927 (4)1.2086 (6)0.40878 (14)0.0447 (9)
O170.0628 (4)1.1847 (5)0.35889 (12)0.0621 (9)
O180.0439 (4)1.3705 (5)0.43550 (13)0.0638 (10)
C190.2604 (6)0.7522 (7)0.35940 (16)0.0544 (12)
H19A0.32500.61180.36020.082*
H19B0.30780.86400.33550.082*
H19C0.14940.71770.34590.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0565 (18)0.0477 (16)0.0350 (16)0.0098 (13)0.0021 (13)0.0058 (13)
C20.054 (3)0.057 (3)0.038 (3)0.007 (2)0.0002 (19)0.004 (2)
C30.059 (3)0.063 (3)0.034 (2)0.001 (2)0.0069 (19)0.005 (2)
C40.052 (3)0.052 (2)0.043 (3)0.003 (2)0.0096 (19)0.001 (2)
C50.036 (2)0.044 (2)0.037 (2)0.0007 (17)0.0037 (17)0.0012 (18)
C60.038 (2)0.039 (2)0.031 (2)0.0014 (17)0.0014 (16)0.0050 (17)
C70.037 (2)0.035 (2)0.040 (2)0.0065 (16)0.0020 (17)0.0012 (17)
C80.032 (2)0.036 (2)0.040 (2)0.0006 (17)0.0009 (16)0.0008 (18)
C90.037 (2)0.036 (2)0.034 (2)0.0043 (17)0.0030 (16)0.0019 (17)
C100.041 (2)0.036 (2)0.043 (2)0.0076 (17)0.0022 (17)0.0010 (18)
O110.0489 (17)0.0432 (15)0.0339 (15)0.0143 (12)0.0002 (12)0.0024 (12)
C120.040 (2)0.042 (2)0.037 (2)0.0005 (18)0.0056 (17)0.0020 (18)
C130.033 (2)0.037 (2)0.037 (2)0.0018 (17)0.0011 (16)0.0044 (18)
O140.094 (3)0.078 (2)0.049 (2)0.039 (2)0.0206 (17)0.0005 (17)
C150.086 (4)0.078 (3)0.043 (3)0.012 (3)0.002 (2)0.014 (2)
N160.043 (2)0.048 (2)0.042 (2)0.0035 (16)0.0002 (16)0.0057 (17)
O170.078 (2)0.068 (2)0.039 (2)0.0113 (16)0.0070 (15)0.0053 (15)
O180.083 (2)0.0529 (18)0.054 (2)0.0318 (17)0.0024 (16)0.0043 (16)
C190.071 (3)0.057 (3)0.035 (2)0.008 (2)0.002 (2)0.004 (2)
Geometric parameters (Å, º) top
O1—C21.361 (5)C9—C101.356 (5)
O1—C61.366 (4)C9—O111.383 (4)
C2—C31.328 (6)C10—H100.9300
C2—C151.472 (6)O11—C121.362 (4)
C3—C41.428 (6)C12—C131.345 (5)
C3—H30.9300C12—C191.473 (5)
C4—O141.233 (5)C13—N161.428 (5)
C4—C51.459 (5)C15—H15A0.9600
C5—C61.390 (5)C15—H15B0.9600
C5—C101.399 (5)C15—H15C0.9600
C6—C71.385 (5)N16—O181.212 (4)
C7—C81.379 (5)N16—O171.226 (4)
C7—H70.9300C19—H19A0.9600
C8—C91.390 (5)C19—H19B0.9600
C8—C131.432 (5)C19—H19C0.9600
C2—O1—C6119.5 (3)C9—C10—C5117.1 (3)
C3—C2—O1122.2 (4)C9—C10—H10121.4
C3—C2—C15126.7 (4)C5—C10—H10121.4
O1—C2—C15111.1 (4)C12—O11—C9107.3 (3)
C2—C3—C4122.5 (4)C13—C12—O11109.4 (3)
C2—C3—H3118.7C13—C12—C19135.0 (4)
C4—C3—H3118.7O11—C12—C19115.6 (3)
O14—C4—C3123.4 (4)C12—C13—N16125.2 (4)
O14—C4—C5121.8 (4)C12—C13—C8109.4 (3)
C3—C4—C5114.8 (4)N16—C13—C8125.3 (3)
C6—C5—C10119.0 (3)C2—C15—H15A109.5
C6—C5—C4119.5 (3)C2—C15—H15B109.5
C10—C5—C4121.5 (3)H15A—C15—H15B109.5
O1—C6—C7115.2 (3)C2—C15—H15C109.5
O1—C6—C5121.5 (3)H15A—C15—H15C109.5
C7—C6—C5123.3 (3)H15B—C15—H15C109.5
C8—C7—C6116.9 (3)O18—N16—O17124.1 (3)
C8—C7—H7121.6O18—N16—C13116.7 (3)
C6—C7—H7121.6O17—N16—C13119.2 (3)
C7—C8—C9119.6 (3)C12—C19—H19A109.5
C7—C8—C13136.6 (3)C12—C19—H19B109.5
C9—C8—C13103.8 (3)H19A—C19—H19B109.5
C10—C9—O11125.8 (3)C12—C19—H19C109.5
C10—C9—C8124.0 (3)H19A—C19—H19C109.5
O11—C9—C8110.1 (3)H19B—C19—H19C109.5
C6—O1—C2—C32.1 (6)C7—C8—C9—O11179.0 (3)
C6—O1—C2—C15178.5 (4)C13—C8—C9—O110.5 (4)
O1—C2—C3—C41.7 (7)O11—C9—C10—C5178.3 (3)
C15—C2—C3—C4179.0 (4)C8—C9—C10—C50.0 (6)
C2—C3—C4—O14179.0 (4)C6—C5—C10—C90.7 (6)
C2—C3—C4—C50.1 (6)C4—C5—C10—C9179.3 (4)
O14—C4—C5—C6177.9 (4)C10—C9—O11—C12178.3 (4)
C3—C4—C5—C61.0 (6)C8—C9—O11—C120.1 (4)
O14—C4—C5—C103.4 (6)C9—O11—C12—C130.7 (4)
C3—C4—C5—C10177.6 (4)C9—O11—C12—C19178.4 (3)
C2—O1—C6—C7179.0 (3)O11—C12—C13—N16179.6 (3)
C2—O1—C6—C50.9 (5)C19—C12—C13—N160.7 (7)
C10—C5—C6—O1178.0 (3)O11—C12—C13—C81.1 (4)
C4—C5—C6—O10.6 (6)C19—C12—C13—C8177.8 (4)
C10—C5—C6—C71.8 (6)C7—C8—C13—C12178.4 (4)
C4—C5—C6—C7179.5 (4)C9—C8—C13—C121.0 (4)
O1—C6—C7—C8177.7 (3)C7—C8—C13—N160.1 (7)
C5—C6—C7—C82.2 (6)C9—C8—C13—N16179.5 (3)
C6—C7—C8—C91.5 (5)C12—C13—N16—O18178.3 (4)
C6—C7—C8—C13177.8 (4)C8—C13—N16—O183.5 (5)
C7—C8—C9—C100.5 (6)C12—C13—N16—O171.8 (6)
C13—C8—C9—C10179.0 (4)C8—C13—N16—O17176.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O180.932.532.985 (5)110
C10—H10···O11i0.932.683.583 (4)164
C7—H7···O18ii0.932.443.309 (5)156
C3—H3···O14iii0.932.743.525 (5)143
C19—H19A···O14i0.962.273.191 (5)160
C15—H15C···O17iv0.962.653.391 (6)134
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3, z+1; (iii) x+1, y+1/2, z+3/2; (iv) x, y+5/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H9NO5
Mr259.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.111 (2), 5.732 (1), 24.235 (5)
β (°) 93.51 (3)
V3)1124.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.6 × 0.25 × 0.03
Data collection
DiffractometerKuma KM-4 CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4062, 1463, 1329
Rint0.079
θmax (°)22.5
(sin θ/λ)max1)0.538
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.168, 1.13
No. of reflections1463
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.28

Computer programs: CrysAlis CCD (Kuma, 1999), CrysAlis RED (Kuma, 1999), CrysAlis RED, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Stereochemical Workstation (Siemens, 1989), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O180.932.532.985 (5)110.4
C10—H10···O11i0.932.683.583 (4)164.1
C7—H7···O18ii0.932.443.309 (5)156.2
C3—H3···O14iii0.932.743.525 (5)142.5
C19—H19A···O14i0.962.273.191 (5)159.7
C15—H15C···O17iv0.962.653.391 (6)133.9
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3, z+1; (iii) x+1, y+1/2, z+3/2; (iv) x, y+5/2, z+1/2.
 

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