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Crystals of 2,6-di­nitro­toluene, C7H6N2O4, were obtained from a methanol solution of the mixture of 2,6- and 2,4-di­nitro­toluene. The P212121 space group shows the compound is chiral, but the absolute configuration was not determined reliably. The nitro group planes are inclined to the benzene plane with dihedral angles of 53.1 (1) and 38.1 (1)°, respectively. The repulsion between methyl and nitro groups results in a rather small C-C-C angle of 112.6 (2)° within the benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013022/cv6049sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013022/cv6049Isup2.hkl
Contains datablock I

CCDC reference: 172202

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.133
  • Data-to-parameter ratio = 8.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLG_01 _reflns_number_observed is an old dataname which has been superseded by _reflns_number_gt REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 1061 Count of symmetry unique reflns 1060 Completeness (_total/calc) 100.09% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Comment top

no comment!

Experimental top

Single crystals of the title chiral compound were obtained from a methanol solution containing 2,6- and 2,4-dinitrotoluene when we tried to separate the isomers.

Refinement top

H atoms were located in calculated positions and ridden on parent C atoms during refinements. The absolute configuration could not be reliably determined.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1985a, 1992a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985b, 1992b); program(s) used to solve structure: SHELXS93 (Sheldrick, 1993); program(s) used to refine structure: SHELXL93; molecular graphics: XP (Siemens, 1994).

Figures top
[Figure 1] Fig. 1. View of the crystal packing of the title compound with 30% probability displacement ellipsoids, showing the overlap of adjacent benzene rings. H atoms have been omitted for clarity.
2,6-Dinitrotoluene top
Crystal data top
C7H6N2O4Dx = 1.548 Mg m3
Mr = 182.14Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 20 reflections
a = 7.830 (2) Åθ = 11.7–21.5°
b = 13.683 (3) ŵ = 0.13 mm1
c = 7.296 (2) ÅT = 293 K
V = 781.7 (3) Å3Prismatic, yellow
Z = 40.30 × 0.24 × 0.20 mm
F(000) = 376
Data collection top
Rigaku AFC-7R
diffractometer
906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
ω/2θ scansh = 010
Absorption correction: psi scan
(North et al., 1968)
k = 017
Tmin = 0.963, Tmax = 0.974l = 09
1061 measured reflections3 standard reflections every 100 reflections
1061 independent reflections intensity decay: 0.3%
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0748P)2 + 0.2426P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1061 reflectionsΔρmax = 0.27 e Å3
119 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL93, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0719 (109)
Crystal data top
C7H6N2O4V = 781.7 (3) Å3
Mr = 182.14Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.830 (2) ŵ = 0.13 mm1
b = 13.683 (3) ÅT = 293 K
c = 7.296 (2) Å0.30 × 0.24 × 0.20 mm
Data collection top
Rigaku AFC-7R
diffractometer
906 reflections with I > 2σ(I)
Absorption correction: psi scan
(North et al., 1968)
Rint = 0.000
Tmin = 0.963, Tmax = 0.9743 standard reflections every 100 reflections
1061 measured reflections intensity decay: 0.3%
1061 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.05Δρmax = 0.27 e Å3
1061 reflectionsΔρmin = 0.23 e Å3
119 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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. 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
O10.8388 (3)0.23852 (14)0.7794 (4)0.0640 (7)
O20.6725 (4)0.2359 (2)1.0143 (5)0.0709 (8)
O30.3958 (3)0.1192 (2)1.0183 (4)0.0665 (7)
O40.5395 (4)0.2154 (2)0.8452 (5)0.0846 (10)
N10.7602 (3)0.1962 (2)0.8992 (4)0.0486 (6)
N20.5215 (3)0.1393 (2)0.9266 (4)0.0503 (6)
C10.6289 (3)0.0320 (2)0.9135 (4)0.0395 (6)
C20.7764 (3)0.0884 (2)0.9082 (5)0.0413 (6)
C30.9412 (4)0.0525 (2)0.9081 (5)0.0475 (7)
H31.0342 (4)0.0947 (2)0.9025 (5)0.057*
C40.9651 (4)0.0477 (2)0.9165 (5)0.0489 (7)
H41.0748 (4)0.0737 (2)0.9209 (5)0.059*
C50.8256 (4)0.1084 (2)0.9182 (5)0.0471 (7)
H50.8401 (4)0.1759 (2)0.9188 (5)0.057*
C60.6635 (3)0.0686 (2)0.9191 (4)0.0400 (6)
C70.4516 (4)0.0738 (2)0.8999 (6)0.0528 (8)
H7A0.3695 (4)0.0218 (2)0.9067 (6)0.079*
H7B0.4392 (4)0.1075 (2)0.7853 (6)0.079*
H7C0.4330 (4)0.1187 (2)0.9990 (6)0.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0618 (13)0.0413 (10)0.089 (2)0.0103 (11)0.0006 (14)0.0130 (12)
O20.078 (2)0.0411 (12)0.094 (2)0.0051 (12)0.013 (2)0.0150 (12)
O30.0462 (12)0.0585 (13)0.095 (2)0.0100 (10)0.0075 (13)0.0034 (14)
O40.078 (2)0.0458 (12)0.130 (3)0.0177 (13)0.001 (2)0.027 (2)
N10.0455 (12)0.0305 (10)0.070 (2)0.0027 (9)0.0062 (14)0.0001 (12)
N20.0430 (12)0.0389 (11)0.069 (2)0.0069 (10)0.0044 (13)0.0003 (13)
C10.0363 (12)0.0333 (12)0.0489 (13)0.0032 (10)0.0002 (13)0.0006 (12)
C20.0407 (13)0.0298 (11)0.053 (2)0.0001 (10)0.0006 (15)0.0022 (12)
C30.0378 (13)0.0425 (14)0.062 (2)0.0053 (11)0.004 (2)0.0046 (15)
C40.0345 (12)0.0471 (14)0.065 (2)0.0072 (11)0.000 (2)0.0036 (15)
C50.0461 (14)0.0340 (12)0.061 (2)0.0068 (11)0.001 (2)0.0013 (13)
C60.0379 (12)0.0299 (11)0.0523 (15)0.0041 (10)0.0014 (14)0.0009 (12)
C70.0397 (13)0.0395 (13)0.079 (2)0.0081 (12)0.002 (2)0.005 (2)
Geometric parameters (Å, º) top
O1—N11.216 (3)C3—C41.386 (4)
O2—N11.213 (4)C3—H30.93
O3—N21.221 (3)C4—C51.372 (4)
O4—N21.206 (4)C4—H40.93
N1—C21.482 (3)C5—C61.382 (4)
N2—C61.476 (3)C5—H50.93
C1—C21.389 (4)C7—H7A0.96
C1—C61.404 (3)C7—H7B0.96
C1—C71.505 (4)C7—H7C0.96
C2—C31.380 (4)
O1—N1—O2124.8 (2)C5—C4—C3119.5 (3)
O1—N1—C2117.5 (3)C5—C4—H4120.3
O2—N1—C2117.6 (3)C3—C4—H4120.3
O4—N2—O3124.0 (3)C4—C5—C6119.5 (2)
O4—N2—C6117.4 (3)C4—C5—H5120.2
O3—N2—C6118.7 (2)C6—C5—H5120.24
C2—C1—C6112.6 (2)C5—C6—C1124.3 (2)
C2—C1—C7123.7 (2)C5—C6—N2115.7 (2)
C6—C1—C7123.5 (2)C1—C6—N2120.0 (2)
C3—C2—C1125.4 (2)C1—C7—H7A109.47
C3—C2—N1115.7 (2)C1—C7—H7B109.5
C1—C2—N1118.8 (2)H7A—C7—H7B109.5
C2—C3—C4118.6 (3)C1—C7—H7C109.5
C2—C3—H3120.7H7A—C7—H7C109.5
C4—C3—H3120.7H7B—C7—H7C109.5

Experimental details

Crystal data
Chemical formulaC7H6N2O4
Mr182.14
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.830 (2), 13.683 (3), 7.296 (2)
V3)781.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.30 × 0.24 × 0.20
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correctionPsi scan
(North et al., 1968)
Tmin, Tmax0.963, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
1061, 1061, 906
Rint0.000
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.133, 1.05
No. of reflections1061
No. of parameters119
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.23

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1985a, 1992a), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1985b, 1992b), SHELXS93 (Sheldrick, 1993), SHELXL93, XP (Siemens, 1994).

Selected geometric parameters (Å, º) top
O1—N11.216 (3)O4—N21.206 (4)
O2—N11.213 (4)N1—C21.482 (3)
O3—N21.221 (3)N2—C61.476 (3)
O1—N1—O2124.8 (2)O4—N2—C6117.4 (3)
O1—N1—C2117.5 (3)O3—N2—C6118.7 (2)
O2—N1—C2117.6 (3)C2—C1—C6112.6 (2)
O4—N2—O3124.0 (3)
 

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