Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021666/kp2103sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021666/kp2103Isup2.hkl |
CCDC reference: 651412
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
The title compound was prepared from HNO3 and 1-tert-butyl-4-methoxybenzene, according to the procedure of Kwiatkowski et al. (1997).
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.
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).
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).
C11H14N2O5 | F(000) = 1072 |
Mr = 254.24 | Dx = 1.332 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 21.7800 (18) Å | θ = 10.0–14.8° |
b = 12.3756 (10) Å | µ = 0.11 mm−1 |
c = 10.0521 (8) Å | T = 298 K |
β = 110.686 (3)° | Prism, colourless |
V = 2534.8 (4) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 8 |
Enraf–Nonius CAD-4 diffractometer | 2411 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 28.2°, θmin = 1.9° |
ω/2–θ scans | h = −28→27 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −16→16 |
Tmin = 0.956, Tmax = 0.979 | l = −12→13 |
16809 measured reflections | 3 standard reflections every 60 min |
3063 independent reflections | intensity decay: 0.3% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-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 reflections | Δρmax = 0.53 e Å−3 |
164 parameters | Δρmin = −0.34 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0056 (9) |
C11H14N2O5 | V = 2534.8 (4) Å3 |
Mr = 254.24 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.7800 (18) Å | µ = 0.11 mm−1 |
b = 12.3756 (10) Å | T = 298 K |
c = 10.0521 (8) Å | 0.30 × 0.25 × 0.20 mm |
β = 110.686 (3)° |
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 = 0.979 | 3 standard reflections every 60 min |
16809 measured reflections | intensity decay: 0.3% |
3063 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.53 e Å−3 |
3063 reflections | Δρmin = −0.34 e Å−3 |
164 parameters |
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 | ||
C9 | 0.41557 (11) | 0.0960 (2) | 0.7960 (2) | 0.0732 (6) | |
H9A | 0.4019 | 0.0243 | 0.8093 | 0.110* | |
H9B | 0.4614 | 0.0955 | 0.8091 | 0.110* | |
H9C | 0.3907 | 0.1204 | 0.7016 | 0.110* | |
C10 | 0.42528 (11) | 0.2866 (2) | 0.8843 (3) | 0.0831 (7) | |
H10A | 0.4001 | 0.3116 | 0.7904 | 0.125* | |
H10B | 0.4710 | 0.2866 | 0.8967 | 0.125* | |
H10C | 0.4181 | 0.3337 | 0.9533 | 0.125* | |
O4 | 0.19977 (9) | 0.33505 (15) | 0.55134 (17) | 0.0828 (5) | |
O5 | 0.12433 (9) | 0.3218 (2) | 0.6367 (3) | 0.1169 (8) | |
C11 | 0.08562 (11) | 0.0967 (2) | 0.6871 (3) | 0.0795 (7) | |
H11A | 0.0417 | 0.0987 | 0.6877 | 0.119* | |
H11B | 0.0997 | 0.0230 | 0.6896 | 0.119* | |
H11C | 0.0868 | 0.1308 | 0.6022 | 0.119* | |
C1 | 0.19258 (7) | 0.15762 (12) | 0.82339 (16) | 0.0407 (3) | |
O1 | 0.12844 (6) | 0.15281 (11) | 0.80883 (14) | 0.0561 (4) | |
C4 | 0.33051 (7) | 0.16977 (12) | 0.88046 (15) | 0.0382 (3) | |
C3 | 0.30526 (8) | 0.10427 (12) | 0.96067 (15) | 0.0406 (3) | |
H3 | 0.3336 | 0.0645 | 1.0359 | 0.049* | |
C2 | 0.23849 (8) | 0.09782 (12) | 0.92962 (16) | 0.0408 (3) | |
C5 | 0.28576 (8) | 0.22938 (12) | 0.77189 (16) | 0.0410 (3) | |
H5 | 0.3010 | 0.2733 | 0.7152 | 0.049* | |
N1 | 0.21527 (8) | 0.02213 (12) | 1.01381 (17) | 0.0525 (4) | |
C6 | 0.21916 (8) | 0.22504 (12) | 0.74620 (15) | 0.0414 (4) | |
O3 | 0.24253 (9) | 0.02423 (13) | 1.14221 (15) | 0.0738 (5) | |
N2 | 0.17748 (8) | 0.29694 (13) | 0.63483 (17) | 0.0568 (4) | |
C7 | 0.40392 (8) | 0.17216 (13) | 0.90428 (17) | 0.0444 (4) | |
O2 | 0.17149 (9) | −0.04078 (14) | 0.95125 (19) | 0.0815 (5) | |
C8 | 0.44524 (9) | 0.1347 (2) | 1.0536 (2) | 0.0700 (6) | |
H8A | 0.4333 | 0.0620 | 1.0677 | 0.105* | |
H8B | 0.4376 | 0.1814 | 1.1224 | 0.105* | |
H8C | 0.4909 | 0.1369 | 1.0648 | 0.105* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C9 | 0.0524 (11) | 0.1024 (17) | 0.0703 (13) | 0.0098 (11) | 0.0283 (10) | −0.0150 (12) |
C10 | 0.0492 (12) | 0.0739 (14) | 0.1155 (19) | −0.0102 (10) | 0.0157 (12) | 0.0228 (13) |
O4 | 0.0792 (11) | 0.0996 (12) | 0.0663 (9) | 0.0261 (9) | 0.0217 (8) | 0.0410 (9) |
O5 | 0.0628 (11) | 0.1358 (18) | 0.1556 (19) | 0.0521 (11) | 0.0429 (12) | 0.0776 (15) |
C11 | 0.0450 (11) | 0.0950 (17) | 0.0886 (16) | −0.0054 (10) | 0.0113 (10) | −0.0152 (13) |
C1 | 0.0381 (8) | 0.0423 (8) | 0.0438 (8) | 0.0050 (6) | 0.0172 (6) | −0.0052 (6) |
O1 | 0.0383 (6) | 0.0667 (8) | 0.0674 (8) | 0.0048 (5) | 0.0239 (6) | −0.0072 (6) |
C4 | 0.0383 (8) | 0.0390 (7) | 0.0372 (7) | 0.0044 (6) | 0.0133 (6) | −0.0008 (5) |
C3 | 0.0428 (8) | 0.0411 (7) | 0.0360 (7) | 0.0048 (6) | 0.0115 (6) | 0.0023 (6) |
C2 | 0.0456 (8) | 0.0400 (7) | 0.0403 (7) | 0.0008 (6) | 0.0194 (6) | −0.0007 (6) |
C5 | 0.0427 (8) | 0.0416 (8) | 0.0400 (8) | 0.0039 (6) | 0.0164 (6) | 0.0039 (6) |
N1 | 0.0566 (9) | 0.0500 (8) | 0.0576 (9) | 0.0001 (7) | 0.0284 (7) | 0.0061 (6) |
C6 | 0.0420 (8) | 0.0419 (8) | 0.0385 (7) | 0.0110 (6) | 0.0120 (6) | 0.0030 (6) |
O3 | 0.1015 (12) | 0.0722 (9) | 0.0528 (8) | −0.0061 (8) | 0.0336 (8) | 0.0140 (7) |
N2 | 0.0479 (9) | 0.0588 (9) | 0.0581 (9) | 0.0158 (7) | 0.0116 (7) | 0.0138 (7) |
C7 | 0.0361 (8) | 0.0512 (9) | 0.0446 (8) | 0.0028 (6) | 0.0127 (6) | 0.0025 (7) |
O2 | 0.0743 (10) | 0.0813 (11) | 0.0888 (11) | −0.0284 (8) | 0.0287 (9) | 0.0089 (8) |
C8 | 0.0400 (9) | 0.1079 (17) | 0.0564 (11) | 0.0121 (10) | 0.0099 (8) | 0.0133 (11) |
C9—C7 | 1.527 (3) | C1—C6 | 1.397 (2) |
C9—H9A | 0.9600 | C4—C3 | 1.387 (2) |
C9—H9B | 0.9600 | C4—C5 | 1.391 (2) |
C9—H9C | 0.9600 | C4—C7 | 1.531 (2) |
C10—C7 | 1.526 (3) | C3—C2 | 1.378 (2) |
C10—H10A | 0.9600 | C3—H3 | 0.9300 |
C10—H10B | 0.9600 | C2—N1 | 1.467 (2) |
C10—H10C | 0.9600 | C5—C6 | 1.382 (2) |
O4—N2 | 1.204 (2) | C5—H5 | 0.9300 |
O5—N2 | 1.204 (2) | N1—O3 | 1.216 (2) |
C11—O1 | 1.429 (3) | N1—O2 | 1.219 (2) |
C11—H11A | 0.9600 | C6—N2 | 1.467 (2) |
C11—H11B | 0.9600 | C7—C8 | 1.525 (2) |
C11—H11C | 0.9600 | C8—H8A | 0.9600 |
C1—O1 | 1.3535 (19) | C8—H8B | 0.9600 |
C1—C2 | 1.391 (2) | C8—H8C | 0.9600 |
C7—C9—H9A | 109.5 | C3—C2—C1 | 123.94 (14) |
C7—C9—H9B | 109.5 | C3—C2—N1 | 117.24 (14) |
H9A—C9—H9B | 109.5 | C1—C2—N1 | 118.81 (14) |
C7—C9—H9C | 109.5 | C6—C5—C4 | 121.65 (14) |
H9A—C9—H9C | 109.5 | C6—C5—H5 | 119.2 |
H9B—C9—H9C | 109.5 | C4—C5—H5 | 119.2 |
C7—C10—H10A | 109.5 | O3—N1—O2 | 124.12 (16) |
C7—C10—H10B | 109.5 | O3—N1—C2 | 117.40 (15) |
H10A—C10—H10B | 109.5 | O2—N1—C2 | 118.44 (15) |
C7—C10—H10C | 109.5 | C5—C6—C1 | 122.22 (14) |
H10A—C10—H10C | 109.5 | C5—C6—N2 | 116.42 (14) |
H10B—C10—H10C | 109.5 | C1—C6—N2 | 121.35 (14) |
O1—C11—H11A | 109.5 | O5—N2—O4 | 122.47 (17) |
O1—C11—H11B | 109.5 | O5—N2—C6 | 118.85 (17) |
H11A—C11—H11B | 109.5 | O4—N2—C6 | 118.45 (15) |
O1—C11—H11C | 109.5 | C8—C7—C10 | 108.10 (18) |
H11A—C11—H11C | 109.5 | C8—C7—C9 | 108.96 (17) |
H11B—C11—H11C | 109.5 | C10—C7—C9 | 110.11 (18) |
O1—C1—C2 | 119.63 (14) | C8—C7—C4 | 111.64 (14) |
O1—C1—C6 | 125.50 (14) | C10—C7—C4 | 110.33 (14) |
C2—C1—C6 | 114.70 (14) | C9—C7—C4 | 107.69 (14) |
C1—O1—C11 | 116.77 (14) | C7—C8—H8A | 109.5 |
C3—C4—C5 | 117.03 (14) | C7—C8—H8B | 109.5 |
C3—C4—C7 | 121.81 (13) | H8A—C8—H8B | 109.5 |
C5—C4—C7 | 121.08 (13) | C7—C8—H8C | 109.5 |
C2—C3—C4 | 120.38 (14) | H8A—C8—H8C | 109.5 |
C2—C3—H3 | 119.8 | H8B—C8—H8C | 109.5 |
C4—C3—H3 | 119.8 | ||
C2—C1—O1—C11 | −108.9 (2) | C4—C5—C6—C1 | −2.7 (2) |
C6—C1—O1—C11 | 76.2 (2) | C4—C5—C6—N2 | 176.15 (14) |
C5—C4—C3—C2 | 1.6 (2) | O1—C1—C6—C5 | 176.70 (14) |
C7—C4—C3—C2 | −175.09 (14) | C2—C1—C6—C5 | 1.5 (2) |
C4—C3—C2—C1 | −2.8 (2) | O1—C1—C6—N2 | −2.0 (2) |
C4—C3—C2—N1 | 176.56 (13) | C2—C1—C6—N2 | −177.23 (14) |
O1—C1—C2—C3 | −174.29 (14) | C5—C6—N2—O5 | −157.4 (2) |
C6—C1—C2—C3 | 1.2 (2) | C1—C6—N2—O5 | 21.5 (3) |
O1—C1—C2—N1 | 6.3 (2) | C5—C6—N2—O4 | 17.3 (2) |
C6—C1—C2—N1 | −178.18 (13) | C1—C6—N2—O4 | −163.92 (18) |
C3—C4—C5—C6 | 1.0 (2) | C3—C4—C7—C8 | −22.9 (2) |
C7—C4—C5—C6 | 177.75 (14) | C5—C4—C7—C8 | 160.45 (16) |
C3—C2—N1—O3 | 47.5 (2) | C3—C4—C7—C10 | −143.18 (18) |
C1—C2—N1—O3 | −133.07 (17) | C5—C4—C7—C10 | 40.2 (2) |
C3—C2—N1—O2 | −130.37 (18) | C3—C4—C7—C9 | 96.62 (18) |
C1—C2—N1—O2 | 49.1 (2) | C5—C4—C7—C9 | −79.98 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O5i | 0.96 | 2.67 | 3.626 (4) | 175 |
C9—H9C···O4ii | 0.96 | 2.67 | 3.610 (3) | 167 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C11H14N2O5 |
Mr | 254.24 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 21.7800 (18), 12.3756 (10), 10.0521 (8) |
β (°) | 110.686 (3) |
V (Å3) | 2534.8 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.956, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16809, 3063, 2411 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.664 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.162, 1.03 |
No. of reflections | 3063 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O5i | 0.96 | 2.67 | 3.626 (4) | 174.5 |
C9—H9C···O4ii | 0.96 | 2.67 | 3.610 (3) | 167.4 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1/2, −y+1/2, −z+1. |
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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.