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The title compound, C11H14N2O5, was prepared by the reaction of HNO3 and 1-tert-butyl-4-methoxy­benzene. The atoms of the benzene ring, the nitro N atoms, the meth­oxy O atom and the tert-butyl tertiary C atom are coplanar; the dihedral angles between this plane and the NO2 planes are 50.41 (18) and 20.2 (3)°. There are weak C—H...O intermol­ecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021666/kp2103sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021666/kp2103Isup2.hkl
Contains datablock I

CCDC reference: 651412

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.051
  • wR factor = 0.162
  • Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A .. O5 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9C .. O4 .. 2.67 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

5-tert-Butyl-2-methoxy-1,3-dinitrobenzene, (I), is an important intermediate in synthesis of Butralin which is a herbicide (Kwiatkowski et al., 1997) and was obtained by the reaction of HNO3 and 1-tert-butyl-4-methoxybenzene, as colourless crystals suitable for X-ray structure analysis.

The molecular structure of (I) is illustrated in Fig. 1. Atoms C1, C2, C3, C4, C5, C6, C7, N1, N2 and O1 are coplanar, the largest deviation being 0.0578 (13) Å for C3. The dihedral angles between the C1—C7/N1/N2/O1 plane and the O2/O3/N1 and O4/O5/N2 planes are 50.41 (18) and 20.21 (29)o, respectively.

Related literature top

For related literature, see: Kwiatkowski et al. (1997).

Experimental top

The title compound was prepared from HNO3 and 1-tert-butyl-4-methoxybenzene, according to the procedure of Kwiatkowski et al. (1997).

Refinement top

H atoms were added at calculated positions and refined using a riding model. H atoms were given isotropic displacement parameters equal to 1.2 (or 1.5 for methyl H atoms) times the equivalent isotropic displacement parameters of their parent atoms and C—H distances were restrained to 0.93 Å for those bonded to phenyl ring, 0.96 Å for those bonded to methyl.

Structure description top

5-tert-Butyl-2-methoxy-1,3-dinitrobenzene, (I), is an important intermediate in synthesis of Butralin which is a herbicide (Kwiatkowski et al., 1997) and was obtained by the reaction of HNO3 and 1-tert-butyl-4-methoxybenzene, as colourless crystals suitable for X-ray structure analysis.

The molecular structure of (I) is illustrated in Fig. 1. Atoms C1, C2, C3, C4, C5, C6, C7, N1, N2 and O1 are coplanar, the largest deviation being 0.0578 (13) Å for C3. The dihedral angles between the C1—C7/N1/N2/O1 plane and the O2/O3/N1 and O4/O5/N2 planes are 50.41 (18) and 20.21 (29)o, respectively.

For related literature, see: Kwiatkowski et al. (1997).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The structure of (I) shown with the 30% probability displacement ellipsoids.
5-tert-Butyl-2-methoxy-1,3-dinitrobenzene top
Crystal data top
C11H14N2O5F(000) = 1072
Mr = 254.24Dx = 1.332 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 21.7800 (18) Åθ = 10.0–14.8°
b = 12.3756 (10) ŵ = 0.11 mm1
c = 10.0521 (8) ÅT = 298 K
β = 110.686 (3)°Prism, colourless
V = 2534.8 (4) Å30.30 × 0.25 × 0.20 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
2411 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 28.2°, θmin = 1.9°
ω/2–θ scansh = 2827
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1616
Tmin = 0.956, Tmax = 0.979l = 1213
16809 measured reflections3 standard reflections every 60 min
3063 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)] = 0.051H-atom parameters constrained
wR(F2) = 0.162 w = 1/[σ2(Fo2) + (0.0801P)2 + 1.6942P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3063 reflectionsΔρmax = 0.53 e Å3
164 parametersΔρmin = 0.34 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0056 (9)
Crystal data top
C11H14N2O5V = 2534.8 (4) Å3
Mr = 254.24Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.7800 (18) ŵ = 0.11 mm1
b = 12.3756 (10) ÅT = 298 K
c = 10.0521 (8) Å0.30 × 0.25 × 0.20 mm
β = 110.686 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
2411 reflections with I > 2σ(I)
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
Rint = 0.024
Tmin = 0.956, Tmax = 0.9793 standard reflections every 60 min
16809 measured reflections intensity decay: 0.3%
3063 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.162H-atom parameters constrained
S = 1.03Δρmax = 0.53 e Å3
3063 reflectionsΔρmin = 0.34 e Å3
164 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 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
C90.41557 (11)0.0960 (2)0.7960 (2)0.0732 (6)
H9A0.40190.02430.80930.110*
H9B0.46140.09550.80910.110*
H9C0.39070.12040.70160.110*
C100.42528 (11)0.2866 (2)0.8843 (3)0.0831 (7)
H10A0.40010.31160.79040.125*
H10B0.47100.28660.89670.125*
H10C0.41810.33370.95330.125*
O40.19977 (9)0.33505 (15)0.55134 (17)0.0828 (5)
O50.12433 (9)0.3218 (2)0.6367 (3)0.1169 (8)
C110.08562 (11)0.0967 (2)0.6871 (3)0.0795 (7)
H11A0.04170.09870.68770.119*
H11B0.09970.02300.68960.119*
H11C0.08680.13080.60220.119*
C10.19258 (7)0.15762 (12)0.82339 (16)0.0407 (3)
O10.12844 (6)0.15281 (11)0.80883 (14)0.0561 (4)
C40.33051 (7)0.16977 (12)0.88046 (15)0.0382 (3)
C30.30526 (8)0.10427 (12)0.96067 (15)0.0406 (3)
H30.33360.06451.03590.049*
C20.23849 (8)0.09782 (12)0.92962 (16)0.0408 (3)
C50.28576 (8)0.22938 (12)0.77189 (16)0.0410 (3)
H50.30100.27330.71520.049*
N10.21527 (8)0.02213 (12)1.01381 (17)0.0525 (4)
C60.21916 (8)0.22504 (12)0.74620 (15)0.0414 (4)
O30.24253 (9)0.02423 (13)1.14221 (15)0.0738 (5)
N20.17748 (8)0.29694 (13)0.63483 (17)0.0568 (4)
C70.40392 (8)0.17216 (13)0.90428 (17)0.0444 (4)
O20.17149 (9)0.04078 (14)0.95125 (19)0.0815 (5)
C80.44524 (9)0.1347 (2)1.0536 (2)0.0700 (6)
H8A0.43330.06201.06770.105*
H8B0.43760.18141.12240.105*
H8C0.49090.13691.06480.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C90.0524 (11)0.1024 (17)0.0703 (13)0.0098 (11)0.0283 (10)0.0150 (12)
C100.0492 (12)0.0739 (14)0.1155 (19)0.0102 (10)0.0157 (12)0.0228 (13)
O40.0792 (11)0.0996 (12)0.0663 (9)0.0261 (9)0.0217 (8)0.0410 (9)
O50.0628 (11)0.1358 (18)0.1556 (19)0.0521 (11)0.0429 (12)0.0776 (15)
C110.0450 (11)0.0950 (17)0.0886 (16)0.0054 (10)0.0113 (10)0.0152 (13)
C10.0381 (8)0.0423 (8)0.0438 (8)0.0050 (6)0.0172 (6)0.0052 (6)
O10.0383 (6)0.0667 (8)0.0674 (8)0.0048 (5)0.0239 (6)0.0072 (6)
C40.0383 (8)0.0390 (7)0.0372 (7)0.0044 (6)0.0133 (6)0.0008 (5)
C30.0428 (8)0.0411 (7)0.0360 (7)0.0048 (6)0.0115 (6)0.0023 (6)
C20.0456 (8)0.0400 (7)0.0403 (7)0.0008 (6)0.0194 (6)0.0007 (6)
C50.0427 (8)0.0416 (8)0.0400 (8)0.0039 (6)0.0164 (6)0.0039 (6)
N10.0566 (9)0.0500 (8)0.0576 (9)0.0001 (7)0.0284 (7)0.0061 (6)
C60.0420 (8)0.0419 (8)0.0385 (7)0.0110 (6)0.0120 (6)0.0030 (6)
O30.1015 (12)0.0722 (9)0.0528 (8)0.0061 (8)0.0336 (8)0.0140 (7)
N20.0479 (9)0.0588 (9)0.0581 (9)0.0158 (7)0.0116 (7)0.0138 (7)
C70.0361 (8)0.0512 (9)0.0446 (8)0.0028 (6)0.0127 (6)0.0025 (7)
O20.0743 (10)0.0813 (11)0.0888 (11)0.0284 (8)0.0287 (9)0.0089 (8)
C80.0400 (9)0.1079 (17)0.0564 (11)0.0121 (10)0.0099 (8)0.0133 (11)
Geometric parameters (Å, º) top
C9—C71.527 (3)C1—C61.397 (2)
C9—H9A0.9600C4—C31.387 (2)
C9—H9B0.9600C4—C51.391 (2)
C9—H9C0.9600C4—C71.531 (2)
C10—C71.526 (3)C3—C21.378 (2)
C10—H10A0.9600C3—H30.9300
C10—H10B0.9600C2—N11.467 (2)
C10—H10C0.9600C5—C61.382 (2)
O4—N21.204 (2)C5—H50.9300
O5—N21.204 (2)N1—O31.216 (2)
C11—O11.429 (3)N1—O21.219 (2)
C11—H11A0.9600C6—N21.467 (2)
C11—H11B0.9600C7—C81.525 (2)
C11—H11C0.9600C8—H8A0.9600
C1—O11.3535 (19)C8—H8B0.9600
C1—C21.391 (2)C8—H8C0.9600
C7—C9—H9A109.5C3—C2—C1123.94 (14)
C7—C9—H9B109.5C3—C2—N1117.24 (14)
H9A—C9—H9B109.5C1—C2—N1118.81 (14)
C7—C9—H9C109.5C6—C5—C4121.65 (14)
H9A—C9—H9C109.5C6—C5—H5119.2
H9B—C9—H9C109.5C4—C5—H5119.2
C7—C10—H10A109.5O3—N1—O2124.12 (16)
C7—C10—H10B109.5O3—N1—C2117.40 (15)
H10A—C10—H10B109.5O2—N1—C2118.44 (15)
C7—C10—H10C109.5C5—C6—C1122.22 (14)
H10A—C10—H10C109.5C5—C6—N2116.42 (14)
H10B—C10—H10C109.5C1—C6—N2121.35 (14)
O1—C11—H11A109.5O5—N2—O4122.47 (17)
O1—C11—H11B109.5O5—N2—C6118.85 (17)
H11A—C11—H11B109.5O4—N2—C6118.45 (15)
O1—C11—H11C109.5C8—C7—C10108.10 (18)
H11A—C11—H11C109.5C8—C7—C9108.96 (17)
H11B—C11—H11C109.5C10—C7—C9110.11 (18)
O1—C1—C2119.63 (14)C8—C7—C4111.64 (14)
O1—C1—C6125.50 (14)C10—C7—C4110.33 (14)
C2—C1—C6114.70 (14)C9—C7—C4107.69 (14)
C1—O1—C11116.77 (14)C7—C8—H8A109.5
C3—C4—C5117.03 (14)C7—C8—H8B109.5
C3—C4—C7121.81 (13)H8A—C8—H8B109.5
C5—C4—C7121.08 (13)C7—C8—H8C109.5
C2—C3—C4120.38 (14)H8A—C8—H8C109.5
C2—C3—H3119.8H8B—C8—H8C109.5
C4—C3—H3119.8
C2—C1—O1—C11108.9 (2)C4—C5—C6—C12.7 (2)
C6—C1—O1—C1176.2 (2)C4—C5—C6—N2176.15 (14)
C5—C4—C3—C21.6 (2)O1—C1—C6—C5176.70 (14)
C7—C4—C3—C2175.09 (14)C2—C1—C6—C51.5 (2)
C4—C3—C2—C12.8 (2)O1—C1—C6—N22.0 (2)
C4—C3—C2—N1176.56 (13)C2—C1—C6—N2177.23 (14)
O1—C1—C2—C3174.29 (14)C5—C6—N2—O5157.4 (2)
C6—C1—C2—C31.2 (2)C1—C6—N2—O521.5 (3)
O1—C1—C2—N16.3 (2)C5—C6—N2—O417.3 (2)
C6—C1—C2—N1178.18 (13)C1—C6—N2—O4163.92 (18)
C3—C4—C5—C61.0 (2)C3—C4—C7—C822.9 (2)
C7—C4—C5—C6177.75 (14)C5—C4—C7—C8160.45 (16)
C3—C2—N1—O347.5 (2)C3—C4—C7—C10143.18 (18)
C1—C2—N1—O3133.07 (17)C5—C4—C7—C1040.2 (2)
C3—C2—N1—O2130.37 (18)C3—C4—C7—C996.62 (18)
C1—C2—N1—O249.1 (2)C5—C4—C7—C979.98 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O5i0.962.673.626 (4)175
C9—H9C···O4ii0.962.673.610 (3)167
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x+1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC11H14N2O5
Mr254.24
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)21.7800 (18), 12.3756 (10), 10.0521 (8)
β (°) 110.686 (3)
V3)2534.8 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.956, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
16809, 3063, 2411
Rint0.024
(sin θ/λ)max1)0.664
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.162, 1.03
No. of reflections3063
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.34

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O5i0.962.673.626 (4)174.5
C9—H9C···O4ii0.962.673.610 (3)167.4
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x+1/2, y+1/2, z+1.
 

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