Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019699/dn6010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019699/dn6010Isup2.hkl |
CCDC reference: 180539
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
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
The synthesis of the title compound has been described elsewhere (Kossakowski & Zawadowski, 1995). Crystals were grown from acetic acid by slow evaporation.
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.
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.
C13H9NO5 | F(000) = 536 |
Mr = 259.21 | Dx = 1.531 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.111 (2) Å | Cell parameters from 2228 reflections |
b = 5.732 (1) Å | θ = 2.5–21.2° |
c = 24.235 (5) Å | µ = 0.12 mm−1 |
β = 93.51 (3)° | T = 293 K |
V = 1124.6 (4) Å3 | Prism, orange |
Z = 4 | 0.6 × 0.25 × 0.03 mm |
Kuma KM-4 CCD diffractometer | 1329 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.079 |
Graphite monochromator | θmax = 22.5°, θmin = 3.7° |
ω/2θ scans | h = −8→8 |
4062 measured reflections | k = −4→6 |
1463 independent reflections | l = −26→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-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 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C13H9NO5 | V = 1124.6 (4) Å3 |
Mr = 259.21 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.111 (2) Å | µ = 0.12 mm−1 |
b = 5.732 (1) Å | T = 293 K |
c = 24.235 (5) Å | 0.6 × 0.25 × 0.03 mm |
β = 93.51 (3)° |
Kuma KM-4 CCD diffractometer | 1329 reflections with I > 2σ(I) |
4062 measured reflections | Rint = 0.079 |
1463 independent reflections | θmax = 22.5° |
R[F2 > 2σ(F2)] = 0.069 | 0 restraints |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.28 e Å−3 |
1463 reflections | Δρmin = −0.28 e Å−3 |
172 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2082 (3) | 1.2345 (4) | 0.63614 (10) | 0.0466 (8) | |
C2 | 0.2591 (5) | 1.1733 (7) | 0.68872 (17) | 0.0498 (11) | |
C3 | 0.3546 (5) | 0.9890 (8) | 0.69977 (17) | 0.0523 (11) | |
H3 | 0.3882 | 0.9573 | 0.7364 | 0.063* | |
C4 | 0.4077 (5) | 0.8374 (7) | 0.65758 (17) | 0.0492 (11) | |
C5 | 0.3491 (5) | 0.9011 (6) | 0.60149 (15) | 0.0391 (10) | |
C6 | 0.2517 (4) | 1.0989 (6) | 0.59301 (15) | 0.0361 (9) | |
C7 | 0.1918 (4) | 1.1731 (6) | 0.54121 (15) | 0.0373 (9) | |
H7 | 0.1300 | 1.3092 | 0.5366 | 0.045* | |
C8 | 0.2281 (4) | 1.0358 (6) | 0.49683 (15) | 0.0359 (9) | |
C9 | 0.3241 (4) | 0.8369 (6) | 0.50553 (15) | 0.0356 (9) | |
C10 | 0.3857 (5) | 0.7647 (6) | 0.55595 (16) | 0.0402 (10) | |
H10 | 0.4495 | 0.6303 | 0.5601 | 0.048* | |
O11 | 0.3429 (3) | 0.7235 (4) | 0.45595 (10) | 0.0421 (7) | |
C12 | 0.2591 (5) | 0.8493 (6) | 0.41564 (16) | 0.0395 (10) | |
C13 | 0.1907 (4) | 1.0374 (6) | 0.43831 (15) | 0.0356 (9) | |
O14 | 0.4981 (4) | 0.6673 (6) | 0.66701 (13) | 0.0746 (11) | |
C15 | 0.1959 (7) | 1.3375 (9) | 0.72908 (19) | 0.0693 (14) | |
H15A | 0.1300 | 1.4548 | 0.7100 | 0.104* | |
H15B | 0.2870 | 1.4102 | 0.7496 | 0.104* | |
H15C | 0.1295 | 1.2545 | 0.7540 | 0.104* | |
N16 | 0.0927 (4) | 1.2086 (6) | 0.40878 (14) | 0.0447 (9) | |
O17 | 0.0628 (4) | 1.1847 (5) | 0.35889 (12) | 0.0621 (9) | |
O18 | 0.0439 (4) | 1.3705 (5) | 0.43550 (13) | 0.0638 (10) | |
C19 | 0.2604 (6) | 0.7522 (7) | 0.35940 (16) | 0.0544 (12) | |
H19A | 0.3250 | 0.6118 | 0.3602 | 0.082* | |
H19B | 0.3078 | 0.8640 | 0.3355 | 0.082* | |
H19C | 0.1494 | 0.7177 | 0.3459 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0565 (18) | 0.0477 (16) | 0.0350 (16) | 0.0098 (13) | −0.0021 (13) | −0.0058 (13) |
C2 | 0.054 (3) | 0.057 (3) | 0.038 (3) | −0.007 (2) | −0.0002 (19) | −0.004 (2) |
C3 | 0.059 (3) | 0.063 (3) | 0.034 (2) | 0.001 (2) | −0.0069 (19) | −0.005 (2) |
C4 | 0.052 (3) | 0.052 (2) | 0.043 (3) | 0.003 (2) | −0.0096 (19) | −0.001 (2) |
C5 | 0.036 (2) | 0.044 (2) | 0.037 (2) | 0.0007 (17) | −0.0037 (17) | −0.0012 (18) |
C6 | 0.038 (2) | 0.039 (2) | 0.031 (2) | 0.0014 (17) | 0.0014 (16) | −0.0050 (17) |
C7 | 0.037 (2) | 0.035 (2) | 0.040 (2) | 0.0065 (16) | −0.0020 (17) | 0.0012 (17) |
C8 | 0.032 (2) | 0.036 (2) | 0.040 (2) | 0.0006 (17) | 0.0009 (16) | −0.0008 (18) |
C9 | 0.037 (2) | 0.036 (2) | 0.034 (2) | 0.0043 (17) | 0.0030 (16) | −0.0019 (17) |
C10 | 0.041 (2) | 0.036 (2) | 0.043 (2) | 0.0076 (17) | −0.0022 (17) | 0.0010 (18) |
O11 | 0.0489 (17) | 0.0432 (15) | 0.0339 (15) | 0.0143 (12) | −0.0002 (12) | −0.0024 (12) |
C12 | 0.040 (2) | 0.042 (2) | 0.037 (2) | 0.0005 (18) | 0.0056 (17) | 0.0020 (18) |
C13 | 0.033 (2) | 0.037 (2) | 0.037 (2) | 0.0018 (17) | −0.0011 (16) | 0.0044 (18) |
O14 | 0.094 (3) | 0.078 (2) | 0.049 (2) | 0.039 (2) | −0.0206 (17) | 0.0005 (17) |
C15 | 0.086 (4) | 0.078 (3) | 0.043 (3) | 0.012 (3) | 0.002 (2) | −0.014 (2) |
N16 | 0.043 (2) | 0.048 (2) | 0.042 (2) | 0.0035 (16) | 0.0002 (16) | 0.0057 (17) |
O17 | 0.078 (2) | 0.068 (2) | 0.039 (2) | 0.0113 (16) | −0.0070 (15) | 0.0053 (15) |
O18 | 0.083 (2) | 0.0529 (18) | 0.054 (2) | 0.0318 (17) | −0.0024 (16) | −0.0043 (16) |
C19 | 0.071 (3) | 0.057 (3) | 0.035 (2) | 0.008 (2) | 0.002 (2) | −0.004 (2) |
O1—C2 | 1.361 (5) | C9—C10 | 1.356 (5) |
O1—C6 | 1.366 (4) | C9—O11 | 1.383 (4) |
C2—C3 | 1.328 (6) | C10—H10 | 0.9300 |
C2—C15 | 1.472 (6) | O11—C12 | 1.362 (4) |
C3—C4 | 1.428 (6) | C12—C13 | 1.345 (5) |
C3—H3 | 0.9300 | C12—C19 | 1.473 (5) |
C4—O14 | 1.233 (5) | C13—N16 | 1.428 (5) |
C4—C5 | 1.459 (5) | C15—H15A | 0.9600 |
C5—C6 | 1.390 (5) | C15—H15B | 0.9600 |
C5—C10 | 1.399 (5) | C15—H15C | 0.9600 |
C6—C7 | 1.385 (5) | N16—O18 | 1.212 (4) |
C7—C8 | 1.379 (5) | N16—O17 | 1.226 (4) |
C7—H7 | 0.9300 | C19—H19A | 0.9600 |
C8—C9 | 1.390 (5) | C19—H19B | 0.9600 |
C8—C13 | 1.432 (5) | C19—H19C | 0.9600 |
C2—O1—C6 | 119.5 (3) | C9—C10—C5 | 117.1 (3) |
C3—C2—O1 | 122.2 (4) | C9—C10—H10 | 121.4 |
C3—C2—C15 | 126.7 (4) | C5—C10—H10 | 121.4 |
O1—C2—C15 | 111.1 (4) | C12—O11—C9 | 107.3 (3) |
C2—C3—C4 | 122.5 (4) | C13—C12—O11 | 109.4 (3) |
C2—C3—H3 | 118.7 | C13—C12—C19 | 135.0 (4) |
C4—C3—H3 | 118.7 | O11—C12—C19 | 115.6 (3) |
O14—C4—C3 | 123.4 (4) | C12—C13—N16 | 125.2 (4) |
O14—C4—C5 | 121.8 (4) | C12—C13—C8 | 109.4 (3) |
C3—C4—C5 | 114.8 (4) | N16—C13—C8 | 125.3 (3) |
C6—C5—C10 | 119.0 (3) | C2—C15—H15A | 109.5 |
C6—C5—C4 | 119.5 (3) | C2—C15—H15B | 109.5 |
C10—C5—C4 | 121.5 (3) | H15A—C15—H15B | 109.5 |
O1—C6—C7 | 115.2 (3) | C2—C15—H15C | 109.5 |
O1—C6—C5 | 121.5 (3) | H15A—C15—H15C | 109.5 |
C7—C6—C5 | 123.3 (3) | H15B—C15—H15C | 109.5 |
C8—C7—C6 | 116.9 (3) | O18—N16—O17 | 124.1 (3) |
C8—C7—H7 | 121.6 | O18—N16—C13 | 116.7 (3) |
C6—C7—H7 | 121.6 | O17—N16—C13 | 119.2 (3) |
C7—C8—C9 | 119.6 (3) | C12—C19—H19A | 109.5 |
C7—C8—C13 | 136.6 (3) | C12—C19—H19B | 109.5 |
C9—C8—C13 | 103.8 (3) | H19A—C19—H19B | 109.5 |
C10—C9—O11 | 125.8 (3) | C12—C19—H19C | 109.5 |
C10—C9—C8 | 124.0 (3) | H19A—C19—H19C | 109.5 |
O11—C9—C8 | 110.1 (3) | H19B—C19—H19C | 109.5 |
C6—O1—C2—C3 | 2.1 (6) | C7—C8—C9—O11 | 179.0 (3) |
C6—O1—C2—C15 | −178.5 (4) | C13—C8—C9—O11 | −0.5 (4) |
O1—C2—C3—C4 | −1.7 (7) | O11—C9—C10—C5 | −178.3 (3) |
C15—C2—C3—C4 | 179.0 (4) | C8—C9—C10—C5 | 0.0 (6) |
C2—C3—C4—O14 | 179.0 (4) | C6—C5—C10—C9 | 0.7 (6) |
C2—C3—C4—C5 | 0.1 (6) | C4—C5—C10—C9 | 179.3 (4) |
O14—C4—C5—C6 | −177.9 (4) | C10—C9—O11—C12 | 178.3 (4) |
C3—C4—C5—C6 | 1.0 (6) | C8—C9—O11—C12 | −0.1 (4) |
O14—C4—C5—C10 | 3.4 (6) | C9—O11—C12—C13 | 0.7 (4) |
C3—C4—C5—C10 | −177.6 (4) | C9—O11—C12—C19 | −178.4 (3) |
C2—O1—C6—C7 | 179.0 (3) | O11—C12—C13—N16 | −179.6 (3) |
C2—O1—C6—C5 | −0.9 (5) | C19—C12—C13—N16 | −0.7 (7) |
C10—C5—C6—O1 | 178.0 (3) | O11—C12—C13—C8 | −1.1 (4) |
C4—C5—C6—O1 | −0.6 (6) | C19—C12—C13—C8 | 177.8 (4) |
C10—C5—C6—C7 | −1.8 (6) | C7—C8—C13—C12 | −178.4 (4) |
C4—C5—C6—C7 | 179.5 (4) | C9—C8—C13—C12 | 1.0 (4) |
O1—C6—C7—C8 | −177.7 (3) | C7—C8—C13—N16 | 0.1 (7) |
C5—C6—C7—C8 | 2.2 (6) | C9—C8—C13—N16 | 179.5 (3) |
C6—C7—C8—C9 | −1.5 (5) | C12—C13—N16—O18 | −178.3 (4) |
C6—C7—C8—C13 | 177.8 (4) | C8—C13—N16—O18 | 3.5 (5) |
C7—C8—C9—C10 | 0.5 (6) | C12—C13—N16—O17 | 1.8 (6) |
C13—C8—C9—C10 | −179.0 (4) | C8—C13—N16—O17 | −176.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O18 | 0.93 | 2.53 | 2.985 (5) | 110 |
C10—H10···O11i | 0.93 | 2.68 | 3.583 (4) | 164 |
C7—H7···O18ii | 0.93 | 2.44 | 3.309 (5) | 156 |
C3—H3···O14iii | 0.93 | 2.74 | 3.525 (5) | 143 |
C19—H19A···O14i | 0.96 | 2.27 | 3.191 (5) | 160 |
C15—H15C···O17iv | 0.96 | 2.65 | 3.391 (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 formula | C13H9NO5 |
Mr | 259.21 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.111 (2), 5.732 (1), 24.235 (5) |
β (°) | 93.51 (3) |
V (Å3) | 1124.6 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.6 × 0.25 × 0.03 |
Data collection | |
Diffractometer | Kuma KM-4 CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4062, 1463, 1329 |
Rint | 0.079 |
θmax (°) | 22.5 |
(sin θ/λ)max (Å−1) | 0.538 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.168, 1.13 |
No. of reflections | 1463 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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.
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O18 | 0.93 | 2.53 | 2.985 (5) | 110.4 |
C10—H10···O11i | 0.93 | 2.68 | 3.583 (4) | 164.1 |
C7—H7···O18ii | 0.93 | 2.44 | 3.309 (5) | 156.2 |
C3—H3···O14iii | 0.93 | 2.74 | 3.525 (5) | 142.5 |
C19—H19A···O14i | 0.96 | 2.27 | 3.191 (5) | 159.7 |
C15—H15C···O17iv | 0.96 | 2.65 | 3.391 (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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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.