organic compounds
of 1,3,5-trimethyl-2,4-dinitrobenzene
aLaboratoire de Cristallographie, Département de Physique, Université Mentouri-Constantine, 25000 Constantine, Algeria, and bUMR 6226 CNRS–Université Rennes 1 `Sciences Chimiques de Rennes', Equipe `Matière Condensée et Systèmes Electroactifs', 263 Avenue du Général Leclerc, F-35042 Rennes, France
*Correspondence e-mail: ouardabrihi@yahoo.fr
In the title compound, C9H10N2O4, the planes of the nitro groups subtend dihedral angles of 55.04 (15) and 63.23 (15)° with that of the aromatic ring. These tilts are in opposite senses and the molecule possesses approximate mirror symmetry about a plane normal to the molecule. In the crystal, molecules form stacks in the [100] direction with adjacent molecules related by translation, although the centroid–centroid separation of 4.136 (5) Å is probably too long to regard as a significant aromatic π–π stacking interaction. An extremely weak C—H⋯O interaction is also present.
Keywords: crystal structure; dinitrobenzene; weak C—H⋯O interaction.
CCDC reference: 1415489
1. Related literature
For the structures and properties of related compounds, see: Tazi et al. (1995); Hernandez et al. (2003).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis RED (Oxford Diffraction, 2002); cell CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 1415489
https://doi.org/10.1107/S2056989015014243/hb7463sup1.cif
contains datablocks ouarda, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014243/hb7463Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015014243/hb7463Isup3.cml
The commercially available compound (Sigma-Aldrich) Was recrystallized from ethanol solution.
All non-H atoms were refined with anisotropic atomic displacement parameters. All H atoms were localized in a Fourier maps but introduced in calculated positions and treated as riding on their parent C atoms with Caryl—Haryl=0.93 Å; Cmethyl—Hmethyl=0.96 Å and Uiso(Hmethyl)=1.5Ueq(Cmethyl) or Uiso(Haryl)=1.2Ueq(Caryl). The atoms of benzene cycle present parameters of atomic displacements weaker than those of the substituent atoms.
For the structures and properties of related compounds, see: Tazi et al. (1995); Hernandez et al. (2003).
Data collection: CrysAlis RED (Oxford Diffraction, 2002); cell
CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).C9H10N2O4 | F(000) = 440 |
Mr = 210.19 | Dx = 1.411 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1062 reflections |
a = 4.136 (5) Å | θ = 3.8–25.0° |
b = 13.916 (5) Å | µ = 0.11 mm−1 |
c = 17.194 (5) Å | T = 293 K |
V = 989.6 (13) Å3 | Needle, colourless |
Z = 4 | 0.1 × 0.08 × 0.08 mm |
Oxford Diffraction Xcalibur diffractometer | 2730 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1302 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
CCD scans | θmax = 32.2°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | h = −5→3 |
Tmin = 0.618, Tmax = 1.000 | k = −19→17 |
3941 measured reflections | l = −25→16 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0312P)2] where P = (Fo2 + 2Fc2)/3 |
2730 reflections | (Δ/σ)max < 0.001 |
139 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C9H10N2O4 | V = 989.6 (13) Å3 |
Mr = 210.19 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 4.136 (5) Å | µ = 0.11 mm−1 |
b = 13.916 (5) Å | T = 293 K |
c = 17.194 (5) Å | 0.1 × 0.08 × 0.08 mm |
Oxford Diffraction Xcalibur diffractometer | 2730 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 1302 reflections with I > 2σ(I) |
Tmin = 0.618, Tmax = 1.000 | Rint = 0.032 |
3941 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | Δρmax = 0.12 e Å−3 |
2730 reflections | Δρmin = −0.15 e Å−3 |
139 parameters |
Experimental. Absorption correction: CrysAlisPro, Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.5095 (6) | 0.13682 (16) | 0.51948 (12) | 0.0830 (9) | |
O2 | 0.4780 (6) | 0.14379 (17) | 0.16111 (14) | 0.0975 (10) | |
O11 | 0.1589 (6) | 0.0227 (2) | 0.51482 (12) | 0.0930 (9) | |
O22 | 0.8082 (7) | 0.22717 (18) | 0.22671 (15) | 0.1057 (11) | |
N1 | 0.3785 (6) | 0.06911 (19) | 0.48712 (13) | 0.0612 (9) | |
N2 | 0.6374 (6) | 0.15688 (17) | 0.21810 (14) | 0.0576 (8) | |
C1 | 0.4961 (5) | 0.04214 (19) | 0.40898 (13) | 0.0446 (8) | |
C2 | 0.5978 (6) | −0.05263 (18) | 0.39734 (15) | 0.0482 (8) | |
C3 | 0.7215 (6) | −0.07338 (17) | 0.32487 (16) | 0.0501 (9) | |
C4 | 0.7380 (6) | −0.00732 (19) | 0.26478 (14) | 0.0466 (8) | |
C5 | 0.6263 (6) | 0.08533 (17) | 0.28156 (15) | 0.0439 (8) | |
C6 | 0.5084 (5) | 0.11344 (17) | 0.35299 (14) | 0.0435 (8) | |
C7 | 0.3848 (8) | 0.21448 (18) | 0.36780 (16) | 0.0664 (11) | |
C8 | 0.8759 (7) | −0.0350 (2) | 0.18697 (15) | 0.0632 (10) | |
C9 | 0.5834 (7) | −0.1295 (2) | 0.45897 (17) | 0.0701 (11) | |
H3 | 0.79817 | −0.13520 | 0.31580 | 0.0601* | |
H7A | 0.30028 | 0.24079 | 0.32036 | 0.0995* | |
H7B | 0.55903 | 0.25404 | 0.38611 | 0.0995* | |
H7C | 0.21682 | 0.21253 | 0.40631 | 0.0995* | |
H8A | 1.00516 | 0.01682 | 0.16721 | 0.0947* | |
H8B | 0.70269 | −0.04818 | 0.15135 | 0.0947* | |
H8C | 1.00773 | −0.09134 | 0.19269 | 0.0947* | |
H9A | 0.66925 | −0.10482 | 0.50682 | 0.1050* | |
H9B | 0.70885 | −0.18397 | 0.44265 | 0.1050* | |
H9C | 0.36286 | −0.14884 | 0.46668 | 0.1050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1139 (17) | 0.0722 (16) | 0.0629 (13) | −0.0037 (15) | −0.0125 (13) | −0.0276 (12) |
O2 | 0.130 (2) | 0.0873 (18) | 0.0751 (14) | −0.0364 (15) | −0.0386 (16) | 0.0295 (14) |
O11 | 0.0756 (14) | 0.129 (2) | 0.0743 (14) | −0.0118 (16) | 0.0166 (12) | −0.0084 (15) |
O22 | 0.126 (2) | 0.0670 (16) | 0.124 (2) | −0.0504 (15) | −0.0339 (17) | 0.0323 (15) |
N1 | 0.0600 (14) | 0.0690 (18) | 0.0547 (14) | 0.0088 (14) | −0.0066 (13) | −0.0055 (14) |
N2 | 0.0685 (15) | 0.0394 (13) | 0.0648 (15) | −0.0027 (12) | −0.0067 (14) | 0.0032 (13) |
C1 | 0.0449 (13) | 0.0466 (14) | 0.0424 (13) | −0.0009 (12) | −0.0070 (12) | −0.0089 (12) |
C2 | 0.0508 (14) | 0.0394 (14) | 0.0545 (15) | −0.0036 (12) | −0.0098 (13) | −0.0029 (13) |
C3 | 0.0570 (16) | 0.0294 (12) | 0.0639 (17) | 0.0000 (11) | −0.0025 (14) | −0.0069 (13) |
C4 | 0.0507 (14) | 0.0362 (14) | 0.0529 (14) | −0.0032 (11) | −0.0020 (12) | −0.0082 (13) |
C5 | 0.0477 (13) | 0.0327 (12) | 0.0513 (15) | −0.0047 (11) | −0.0106 (13) | 0.0033 (12) |
C6 | 0.0437 (13) | 0.0353 (12) | 0.0515 (15) | 0.0042 (11) | −0.0110 (12) | −0.0090 (12) |
C7 | 0.083 (2) | 0.0434 (16) | 0.0727 (19) | 0.0206 (15) | −0.0153 (16) | −0.0123 (15) |
C8 | 0.0709 (19) | 0.0503 (16) | 0.0683 (17) | −0.0045 (15) | 0.0121 (15) | −0.0125 (15) |
C9 | 0.082 (2) | 0.0544 (19) | 0.074 (2) | −0.0040 (18) | −0.0028 (16) | 0.0144 (16) |
O1—N1 | 1.221 (3) | C5—C6 | 1.378 (3) |
O2—N2 | 1.195 (3) | C6—C7 | 1.518 (4) |
O11—N1 | 1.212 (4) | C3—H3 | 0.9300 |
O22—N2 | 1.216 (4) | C7—H7A | 0.9600 |
N1—C1 | 1.477 (3) | C7—H7B | 0.9600 |
N2—C5 | 1.478 (3) | C7—H7C | 0.9600 |
C1—C2 | 1.399 (4) | C8—H8A | 0.9600 |
C1—C6 | 1.383 (3) | C8—H8B | 0.9600 |
C2—C3 | 1.378 (4) | C8—H8C | 0.9600 |
C2—C9 | 1.507 (4) | C9—H9A | 0.9600 |
C3—C4 | 1.385 (4) | C9—H9B | 0.9600 |
C4—C5 | 1.400 (4) | C9—H9C | 0.9600 |
C4—C8 | 1.505 (4) | ||
O1—N1—O11 | 124.4 (2) | C5—C6—C7 | 122.1 (2) |
O1—N1—C1 | 117.7 (2) | C2—C3—H3 | 118.00 |
O11—N1—C1 | 118.0 (2) | C4—C3—H3 | 118.00 |
O2—N2—O22 | 122.9 (3) | C6—C7—H7A | 109.00 |
O2—N2—C5 | 119.1 (2) | C6—C7—H7B | 109.00 |
O22—N2—C5 | 118.1 (2) | C6—C7—H7C | 109.00 |
N1—C1—C2 | 118.0 (2) | H7A—C7—H7B | 109.00 |
N1—C1—C6 | 117.6 (2) | H7A—C7—H7C | 109.00 |
C2—C1—C6 | 124.5 (2) | H7B—C7—H7C | 109.00 |
C1—C2—C3 | 116.0 (2) | C4—C8—H8A | 109.00 |
C1—C2—C9 | 123.8 (2) | C4—C8—H8B | 109.00 |
C3—C2—C9 | 120.1 (2) | C4—C8—H8C | 109.00 |
C2—C3—C4 | 123.7 (2) | H8A—C8—H8B | 109.00 |
C3—C4—C5 | 116.2 (2) | H8A—C8—H8C | 109.00 |
C3—C4—C8 | 120.8 (2) | H8B—C8—H8C | 109.00 |
C5—C4—C8 | 123.0 (2) | C2—C9—H9A | 110.00 |
N2—C5—C4 | 117.3 (2) | C2—C9—H9B | 109.00 |
N2—C5—C6 | 118.5 (2) | C2—C9—H9C | 109.00 |
C4—C5—C6 | 124.2 (2) | H9A—C9—H9B | 109.00 |
C1—C6—C5 | 115.4 (2) | H9A—C9—H9C | 109.00 |
C1—C6—C7 | 122.4 (2) | H9B—C9—H9C | 109.00 |
O1—N1—C1—C2 | 124.4 (3) | C6—C1—C2—C3 | 1.0 (4) |
O11—N1—C1—C2 | −55.6 (3) | N1—C1—C6—C5 | 178.6 (2) |
O1—N1—C1—C6 | −53.5 (3) | C1—C2—C3—C4 | −2.2 (4) |
O11—N1—C1—C6 | 126.6 (3) | C9—C2—C3—C4 | 178.9 (2) |
O2—N2—C5—C6 | −116.9 (3) | C2—C3—C4—C5 | 1.3 (4) |
O2—N2—C5—C4 | 63.2 (3) | C2—C3—C4—C8 | −179.9 (2) |
O22—N2—C5—C4 | −117.2 (3) | C3—C4—C5—C6 | 0.9 (4) |
O22—N2—C5—C6 | 62.7 (3) | C8—C4—C5—N2 | 2.0 (4) |
N1—C1—C2—C3 | −176.7 (2) | C8—C4—C5—C6 | −177.9 (2) |
N1—C1—C6—C7 | −4.4 (3) | C3—C4—C5—N2 | −179.2 (2) |
C2—C1—C6—C5 | 1.0 (3) | N2—C5—C6—C1 | 178.2 (2) |
C2—C1—C6—C7 | 178.0 (2) | N2—C5—C6—C7 | 1.2 (4) |
C6—C1—C2—C9 | 179.9 (2) | C4—C5—C6—C1 | −1.9 (4) |
N1—C1—C2—C9 | 2.2 (4) | C4—C5—C6—C7 | −179.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7C···O1i | 0.96 | 2.60 | 3.232 (4) | 124 |
Symmetry code: (i) x−1/2, −y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7C···O1i | 0.96 | 2.60 | 3.232 (4) | 124 |
Symmetry code: (i) x−1/2, −y+1/2, −z+1. |
References
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