




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809046807/dn2510sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809046807/dn2510Isup2.hkl |
CCDC reference: 758268
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.050
- wR factor = 0.119
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 2 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 1
Alert level G PLAT128_ALERT_4_G Non-standard setting of Space-group P21/c .... P21/n
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The position of the H3A atom was obtained from a difference map of the electron density in the unit-cell and its coordinates were refined freely with Uiso(H) = 1.5Ueq(O) .
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).
C7H5NO4 | F(000) = 344 |
Mr = 167.12 | Dx = 1.563 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8368 reflections |
a = 7.2580 (17) Å | θ = 1.8–27.3° |
b = 8.3960 (13) Å | µ = 0.13 mm−1 |
c = 11.704 (3) Å | T = 296 K |
β = 95.165 (18)° | Prism., red |
V = 710.3 (3) Å3 | 0.54 × 0.28 × 0.15 mm |
Z = 4 |
Stoe IPDS II diffractometer | 1396 independent reflections |
Radiation source: fine-focus sealed tube | 944 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.0° |
rotation method scans | h = −8→8 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −10→10 |
Tmin = 0.979, Tmax = 0.992 | l = −14→14 |
4345 measured reflections |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.05P)2 + 0.0581P] where P = (Fo2 + 2Fc2)/3 |
1396 reflections | (Δ/σ)max < 0.001 |
112 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C7H5NO4 | V = 710.3 (3) Å3 |
Mr = 167.12 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.2580 (17) Å | µ = 0.13 mm−1 |
b = 8.3960 (13) Å | T = 296 K |
c = 11.704 (3) Å | 0.54 × 0.28 × 0.15 mm |
β = 95.165 (18)° |
Stoe IPDS II diffractometer | 1396 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 944 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.992 | Rint = 0.062 |
4345 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.16 e Å−3 |
1396 reflections | Δρmin = −0.15 e Å−3 |
112 parameters |
Experimental. 168 frames, detector distance = 120 mm |
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 | ||
O1 | 0.4340 (3) | −0.1006 (2) | 0.25586 (14) | 0.0788 (6) | |
O2 | 0.3658 (3) | −0.3022 (2) | 0.15003 (16) | 0.0819 (6) | |
O3 | 0.1019 (3) | 0.2346 (2) | −0.19209 (14) | 0.0702 (6) | |
H3A | 0.130 (4) | 0.336 (4) | −0.162 (3) | 0.105* | |
O4 | 0.2251 (3) | 0.4736 (2) | −0.06415 (16) | 0.0895 (7) | |
N1 | 0.3709 (3) | −0.1591 (2) | 0.16564 (16) | 0.0524 (5) | |
C1 | 0.3019 (3) | −0.0545 (2) | 0.07198 (17) | 0.0425 (5) | |
C2 | 0.2232 (3) | −0.1209 (2) | −0.03011 (17) | 0.0459 (5) | |
H2 | 0.2154 | −0.2309 | −0.0385 | 0.055* | |
C3 | 0.1574 (3) | −0.0228 (3) | −0.11799 (18) | 0.0494 (5) | |
H3 | 0.1037 | −0.0659 | −0.1863 | 0.059* | |
C4 | 0.1711 (3) | 0.1417 (2) | −0.10464 (18) | 0.0471 (5) | |
C5 | 0.2551 (3) | 0.2073 (2) | −0.00295 (17) | 0.0437 (5) | |
C6 | 0.3190 (3) | 0.1067 (2) | 0.08585 (17) | 0.0431 (5) | |
H6 | 0.3730 | 0.1485 | 0.1544 | 0.052* | |
C7 | 0.2771 (3) | 0.3784 (3) | 0.0104 (2) | 0.0631 (7) | |
H7 | 0.3338 | 0.4172 | 0.0792 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1123 (15) | 0.0673 (12) | 0.0522 (10) | −0.0024 (11) | −0.0171 (10) | 0.0069 (9) |
O2 | 0.1202 (16) | 0.0391 (10) | 0.0829 (13) | 0.0026 (9) | −0.0101 (11) | 0.0101 (8) |
O3 | 0.0914 (13) | 0.0556 (11) | 0.0590 (11) | 0.0048 (9) | −0.0195 (9) | 0.0061 (8) |
O4 | 0.1338 (17) | 0.0423 (10) | 0.0871 (14) | 0.0022 (11) | −0.0199 (12) | 0.0094 (9) |
N1 | 0.0593 (11) | 0.0433 (12) | 0.0547 (11) | −0.0005 (9) | 0.0047 (9) | 0.0071 (9) |
C1 | 0.0418 (11) | 0.0382 (12) | 0.0475 (12) | −0.0002 (9) | 0.0041 (9) | 0.0023 (9) |
C2 | 0.0486 (12) | 0.0355 (10) | 0.0535 (12) | −0.0007 (9) | 0.0046 (9) | −0.0025 (9) |
C3 | 0.0526 (12) | 0.0492 (13) | 0.0453 (12) | −0.0032 (10) | −0.0013 (9) | −0.0086 (10) |
C4 | 0.0463 (11) | 0.0458 (13) | 0.0480 (12) | 0.0029 (9) | −0.0018 (9) | 0.0028 (10) |
C5 | 0.0468 (11) | 0.0366 (11) | 0.0470 (12) | −0.0014 (9) | 0.0007 (9) | −0.0008 (9) |
C6 | 0.0457 (11) | 0.0418 (12) | 0.0413 (11) | −0.0031 (9) | 0.0009 (9) | −0.0049 (9) |
C7 | 0.0805 (17) | 0.0424 (13) | 0.0643 (15) | −0.0020 (12) | −0.0045 (12) | −0.0008 (12) |
O1—N1 | 1.216 (2) | C2—H2 | 0.9300 |
O2—N1 | 1.215 (2) | C3—C4 | 1.392 (3) |
O3—C4 | 1.348 (2) | C3—H3 | 0.9300 |
O3—H3A | 0.93 (3) | C4—C5 | 1.401 (3) |
O4—C7 | 1.218 (3) | C5—C6 | 1.386 (3) |
N1—C1 | 1.458 (3) | C5—C7 | 1.452 (3) |
C1—C6 | 1.367 (3) | C6—H6 | 0.9300 |
C1—C2 | 1.394 (3) | C7—H7 | 0.9300 |
C2—C3 | 1.370 (3) | ||
C4—O3—H3A | 100.5 (19) | O3—C4—C3 | 118.12 (19) |
O2—N1—O1 | 122.27 (19) | O3—C4—C5 | 121.43 (19) |
O2—N1—C1 | 118.59 (19) | C3—C4—C5 | 120.45 (19) |
O1—N1—C1 | 119.13 (18) | C6—C5—C4 | 119.19 (18) |
C6—C1—C2 | 121.56 (19) | C6—C5—C7 | 119.77 (19) |
C6—C1—N1 | 119.05 (18) | C4—C5—C7 | 121.04 (19) |
C2—C1—N1 | 119.38 (18) | C1—C6—C5 | 119.59 (19) |
C3—C2—C1 | 119.5 (2) | C1—C6—H6 | 120.2 |
C3—C2—H2 | 120.3 | C5—C6—H6 | 120.2 |
C1—C2—H2 | 120.3 | O4—C7—C5 | 123.3 (2) |
C2—C3—C4 | 119.71 (19) | O4—C7—H7 | 118.4 |
C2—C3—H3 | 120.1 | C5—C7—H7 | 118.4 |
C4—C3—H3 | 120.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O4i | 0.93 | 2.50 | 3.427 (3) | 175 |
C6—H6···O3ii | 0.93 | 2.53 | 3.433 (3) | 163 |
C7—H7···O2iii | 0.93 | 2.50 | 3.176 (3) | 130 |
O3—H3A···O4 | 0.93 (3) | 1.73 (3) | 2.613 (3) | 157 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C7H5NO4 |
Mr | 167.12 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 7.2580 (17), 8.3960 (13), 11.704 (3) |
β (°) | 95.165 (18) |
V (Å3) | 710.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.54 × 0.28 × 0.15 |
Data collection | |
Diffractometer | Stoe IPDS II diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.979, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4345, 1396, 944 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.119, 1.06 |
No. of reflections | 1396 |
No. of parameters | 112 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.15 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O4i | 0.93 | 2.50 | 3.427 (3) | 174.8 |
C6—H6···O3ii | 0.93 | 2.53 | 3.433 (3) | 163.2 |
C7—H7···O2iii | 0.93 | 2.50 | 3.176 (3) | 129.6 |
O3—H3A···O4 | 0.93 (3) | 1.73 (3) | 2.613 (3) | 157 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) x, y+1, z. |
Nitroaromatics are widely used either as materials or as intermediates in explosives, dyestuffs, pesticides and organic synthesis (Yan et al., 2006). Nitroaromatics occur as industrial wastes and direct pollutants in the environment, and are relatively soluble in water and detectable in rivers, ponds and soil (Yan et al., 2006; Soojhawon et al., 2005). Morover, aromatic compounds with multiple nitro substituents are known to be resistant to electrophilic attack by oxygenases (Halas et al., 1983).
In the title compound (I, Fig. 1), the molecule is essentially planar with a maximum deviation from the mean plane of 0.0116 (11) Å for atom O3. The bond lengths and angles in (I) have normal values, and are comparable with those in the related structures (Rizal et al., 2008; Garden et al., 2004). The dihedral angle between the aromatic ring and the nitro group is 3.83 (3)°.
An intramolecular O3-H33···O4 interaction (Table 1, and Fig. 1) generates an S(6) ring motif (Bernstein et al., 1995). In the crystal structure, the molecules are linked by intermolecular C2-H2···O4, C6-H6···O3 and C7-H7···O7 interactions into a three-dimensional framework. The C-H···O interactions result in the formation of C(5) chain but also R22(8) ring forming an approximately planar network parallel to the (1 0 -1) plane (Fig. 2). These planes are interconnected through π-π interaction which occurs between Cg1 (the centroid of the C1-C6 ring) and its symmetry equivalent at (-x,-y,-z), with a centroid-to-centroid distance of 3.582 (2) Å, a plane-to-plane separation of 3.367 (1) Å and a slippage of 1.22 Å.