organic compounds
2-tert-Butyl-6-[(4-chloro-2-nitrophenyl)diazenyl]-4-methylphenol
aState Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, People's Republic of China, and bDepartment of Chemistry, Nanchang University, Nanchang 330047, People's Republic of China
*Correspondence e-mail: hlwen70@163.com
In the title compound, C17H18ClN3O3, the dihedral angle between the planes of the two benzene rings is 1.03 (7)°. The overall conformation of the molecule is influenced, in part, by electron delocalization and by an intramolecular bifurcated O—H⋯(O,N) hydrogen bonds. The O atoms of the nitro group, one of which serves as an H bond acceptor, are disordered over two sets of sites with refined occupancies of 0.56 (3) and 0.44 (3).
Related literature
For benzotriazoles as UV absorbers and their applications in industry, see: Ravichandran et al. (2002). N-oxides are a key type intermediates in the synthesis of benzotriazoles, see: Wen et al. (2006); Crawford (1999). For the use of green synthetic methods to obtain intermediates, see: Tanaka & Toda (2000).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809019631/lh2824sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809019631/lh2824Isup2.hkl
The title compound was synthesized via the solid phase reaction of 4-chloro-2-nitroaniline and 2-tert-butyl-4-substituted phenol at room temperature. After intensive grinding a mixture of 4-chloro-2-nitrobenzenamine 1.72 g (10 mmol), 2-tert-butyl-4-methylphenol 1.72 g (10.5 mmol), NaNO2 0.69 g (10 mmol), and KHSO4 1.36 g (10 mmol) in a mortar for 15 min at 293 K, the product was washed with hot water. A few purple crystals suitable for X-ray
were obtained upon recrystallization in ethanol after several days (m. p. 445–446 K), which gave the product in 93% yield and higher than 99% purity (by HPLC).All H atoms were included in calculated positions with O—H = 0.82Å; C—H(methyl) = 0.96 Å, C—H(aromatic) = 0.93 Å, and Uiso(H) = 1.5Ueq(Cmethyl,O) and Uiso(H) = 1.2Ueq(C) for aromatic H atoms. The O atoms of the nitro group are disordered over two sites with refined occupancies of 0.56 (3) and 0.44 (3).
Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C17H18ClN3O3 | F(000) = 728 |
Mr = 347.79 | Dx = 1.342 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4044 reflections |
a = 14.578 (4) Å | θ = 2.6–27.2° |
b = 7.0616 (19) Å | µ = 0.24 mm−1 |
c = 17.043 (5) Å | T = 296 K |
β = 101.233 (3)° | Block, purple |
V = 1720.9 (8) Å3 | 0.31 × 0.18 × 0.16 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 3927 independent reflections |
Radiation source: fine-focus sealed tube | 2563 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→18 |
Tmin = 0.930, Tmax = 0.963 | k = −9→8 |
14642 measured reflections | l = −22→22 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0591P)2 + 0.5672P] where P = (Fo2 + 2Fc2)/3 |
3927 reflections | (Δ/σ)max = 0.002 |
241 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C17H18ClN3O3 | V = 1720.9 (8) Å3 |
Mr = 347.79 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.578 (4) Å | µ = 0.24 mm−1 |
b = 7.0616 (19) Å | T = 296 K |
c = 17.043 (5) Å | 0.31 × 0.18 × 0.16 mm |
β = 101.233 (3)° |
Bruker APEXII CCD diffractometer | 3927 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2563 reflections with I > 2σ(I) |
Tmin = 0.930, Tmax = 0.963 | Rint = 0.033 |
14642 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.22 e Å−3 |
3927 reflections | Δρmin = −0.26 e Å−3 |
241 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 | Occ. (<1) | |
Cl1 | 1.37753 (4) | 0.52156 (11) | 0.44085 (5) | 0.0871 (3) | |
O1 | 0.9625 (4) | 0.559 (3) | 0.2905 (6) | 0.109 (4) | 0.56 (3) |
O2 | 1.0758 (7) | 0.659 (2) | 0.2334 (6) | 0.115 (4) | 0.56 (3) |
O3 | 0.81516 (9) | 0.7932 (3) | 0.36241 (8) | 0.0666 (5) | |
H3 | 0.8703 | 0.7643 | 0.3663 | 0.100* | |
O1' | 0.9670 (8) | 0.689 (4) | 0.2804 (4) | 0.100 (5) | 0.44 (3) |
O2' | 1.0687 (12) | 0.545 (5) | 0.2372 (10) | 0.156 (8) | 0.44 (3) |
N1 | 1.04252 (15) | 0.6167 (4) | 0.29115 (12) | 0.0765 (6) | |
N2 | 0.98233 (10) | 0.7293 (2) | 0.43581 (9) | 0.0475 (4) | |
N3 | 0.96277 (10) | 0.7767 (2) | 0.50347 (9) | 0.0468 (4) | |
C1 | 1.10633 (13) | 0.6202 (3) | 0.36932 (12) | 0.0528 (5) | |
C2 | 1.19824 (14) | 0.5718 (3) | 0.36947 (14) | 0.0597 (5) | |
H2 | 1.2171 | 0.5395 | 0.3221 | 0.072* | |
C3 | 1.26084 (14) | 0.5723 (3) | 0.44035 (15) | 0.0599 (6) | |
C4 | 1.23301 (14) | 0.6162 (3) | 0.51114 (14) | 0.0606 (5) | |
H4 | 1.2760 | 0.6122 | 0.5592 | 0.073* | |
C5 | 1.14154 (13) | 0.6660 (3) | 0.51035 (12) | 0.0537 (5) | |
H5 | 1.1233 | 0.6963 | 0.5582 | 0.064* | |
C6 | 1.07582 (12) | 0.6716 (3) | 0.43917 (11) | 0.0468 (4) | |
C7 | 0.87202 (12) | 0.8321 (3) | 0.50305 (10) | 0.0425 (4) | |
C8 | 0.85301 (13) | 0.8758 (3) | 0.57888 (11) | 0.0465 (4) | |
H8 | 0.9010 | 0.8707 | 0.6236 | 0.056* | |
C9 | 0.76528 (13) | 0.9255 (3) | 0.58763 (10) | 0.0473 (4) | |
C10 | 0.69528 (13) | 0.9379 (3) | 0.51815 (11) | 0.0485 (5) | |
H10 | 0.6358 | 0.9748 | 0.5242 | 0.058* | |
C11 | 0.70815 (12) | 0.8993 (3) | 0.44168 (10) | 0.0485 (5) | |
C12 | 0.79931 (12) | 0.8412 (3) | 0.43353 (10) | 0.0465 (4) | |
C13 | 0.74126 (16) | 0.9610 (4) | 0.66868 (11) | 0.0646 (6) | |
H13A | 0.7066 | 0.8553 | 0.6831 | 0.097* | |
H13B | 0.7042 | 1.0738 | 0.6666 | 0.097* | |
H13C | 0.7978 | 0.9763 | 0.7078 | 0.097* | |
C14 | 0.62867 (14) | 0.9137 (4) | 0.36802 (12) | 0.0658 (6) | |
C15 | 0.53856 (16) | 0.9904 (5) | 0.39088 (14) | 0.0868 (9) | |
H15A | 0.5192 | 0.9069 | 0.4290 | 0.130* | |
H15B | 0.4901 | 0.9979 | 0.3439 | 0.130* | |
H15C | 0.5502 | 1.1142 | 0.4139 | 0.130* | |
C16 | 0.65620 (18) | 1.0504 (5) | 0.30642 (14) | 0.0959 (10) | |
H16A | 0.6645 | 1.1753 | 0.3290 | 0.144* | |
H16B | 0.6077 | 1.0528 | 0.2594 | 0.144* | |
H16C | 0.7136 | 1.0087 | 0.2924 | 0.144* | |
C17 | 0.60711 (17) | 0.7157 (5) | 0.33203 (15) | 0.0931 (10) | |
H17A | 0.6629 | 0.6623 | 0.3190 | 0.140* | |
H17B | 0.5598 | 0.7250 | 0.2844 | 0.140* | |
H17C | 0.5852 | 0.6360 | 0.3701 | 0.140* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0412 (3) | 0.1022 (5) | 0.1217 (6) | 0.0083 (3) | 0.0251 (3) | 0.0142 (4) |
O1 | 0.052 (2) | 0.186 (11) | 0.084 (3) | −0.001 (4) | −0.001 (2) | −0.047 (5) |
O2 | 0.105 (4) | 0.185 (9) | 0.056 (3) | −0.001 (5) | 0.016 (3) | 0.012 (4) |
O3 | 0.0420 (7) | 0.1165 (13) | 0.0417 (7) | 0.0091 (8) | 0.0094 (6) | −0.0118 (8) |
O1' | 0.070 (4) | 0.173 (13) | 0.055 (3) | 0.043 (5) | 0.007 (2) | −0.013 (4) |
O2' | 0.115 (7) | 0.255 (18) | 0.091 (7) | 0.062 (10) | 0.007 (5) | −0.080 (9) |
N1 | 0.0612 (13) | 0.1073 (17) | 0.0606 (12) | 0.0158 (13) | 0.0106 (10) | −0.0208 (12) |
N2 | 0.0388 (8) | 0.0553 (10) | 0.0491 (9) | −0.0003 (7) | 0.0102 (7) | −0.0025 (7) |
N3 | 0.0412 (8) | 0.0512 (9) | 0.0478 (9) | −0.0017 (7) | 0.0083 (7) | −0.0007 (7) |
C1 | 0.0465 (11) | 0.0550 (12) | 0.0571 (12) | 0.0003 (9) | 0.0106 (9) | −0.0026 (9) |
C2 | 0.0503 (12) | 0.0634 (14) | 0.0702 (14) | 0.0041 (10) | 0.0232 (11) | 0.0006 (11) |
C3 | 0.0385 (10) | 0.0570 (13) | 0.0869 (16) | 0.0007 (9) | 0.0186 (11) | 0.0079 (11) |
C4 | 0.0429 (11) | 0.0655 (13) | 0.0699 (14) | −0.0021 (9) | 0.0021 (10) | 0.0061 (11) |
C5 | 0.0455 (11) | 0.0588 (12) | 0.0561 (12) | −0.0017 (9) | 0.0084 (9) | 0.0023 (9) |
C6 | 0.0394 (9) | 0.0460 (10) | 0.0554 (11) | −0.0029 (8) | 0.0104 (8) | −0.0006 (8) |
C7 | 0.0374 (9) | 0.0472 (10) | 0.0425 (9) | −0.0019 (7) | 0.0072 (7) | −0.0006 (8) |
C8 | 0.0469 (10) | 0.0531 (11) | 0.0378 (9) | −0.0022 (8) | 0.0038 (8) | 0.0008 (8) |
C9 | 0.0515 (11) | 0.0542 (11) | 0.0380 (9) | −0.0012 (9) | 0.0131 (8) | 0.0004 (8) |
C10 | 0.0418 (10) | 0.0617 (12) | 0.0441 (10) | 0.0039 (8) | 0.0139 (8) | 0.0015 (9) |
C11 | 0.0402 (10) | 0.0668 (13) | 0.0384 (9) | −0.0008 (9) | 0.0074 (7) | 0.0002 (9) |
C12 | 0.0418 (10) | 0.0606 (12) | 0.0381 (9) | 0.0003 (8) | 0.0102 (8) | −0.0032 (8) |
C13 | 0.0651 (13) | 0.0909 (17) | 0.0408 (10) | 0.0048 (12) | 0.0178 (10) | −0.0003 (11) |
C14 | 0.0399 (11) | 0.115 (2) | 0.0415 (10) | 0.0116 (11) | 0.0065 (8) | −0.0021 (11) |
C15 | 0.0470 (12) | 0.156 (3) | 0.0552 (13) | 0.0292 (15) | 0.0053 (10) | 0.0027 (15) |
C16 | 0.0679 (16) | 0.170 (3) | 0.0488 (13) | 0.0225 (18) | 0.0092 (11) | 0.0315 (16) |
C17 | 0.0536 (14) | 0.154 (3) | 0.0663 (15) | −0.0061 (16) | −0.0019 (11) | −0.0380 (17) |
Cl1—C3 | 1.737 (2) | C8—H8 | 0.9300 |
O1—N1 | 1.233 (8) | C9—C10 | 1.407 (3) |
O2—N1 | 1.217 (8) | C9—C13 | 1.511 (2) |
O3—C12 | 1.322 (2) | C10—C11 | 1.379 (2) |
O3—H3 | 0.8200 | C10—H10 | 0.9300 |
O1'—N1 | 1.195 (7) | C11—C12 | 1.423 (2) |
O2'—N1 | 1.179 (10) | C11—C14 | 1.537 (3) |
N1—C1 | 1.469 (3) | C13—H13A | 0.9600 |
N2—N3 | 1.285 (2) | C13—H13B | 0.9600 |
N2—C6 | 1.413 (2) | C13—H13C | 0.9600 |
N3—C7 | 1.378 (2) | C14—C17 | 1.534 (4) |
C1—C2 | 1.382 (3) | C14—C16 | 1.536 (4) |
C1—C6 | 1.397 (3) | C14—C15 | 1.540 (3) |
C2—C3 | 1.365 (3) | C15—H15A | 0.9600 |
C2—H2 | 0.9300 | C15—H15B | 0.9600 |
C3—C4 | 1.381 (3) | C15—H15C | 0.9600 |
C4—C5 | 1.376 (3) | C16—H16A | 0.9600 |
C4—H4 | 0.9300 | C16—H16B | 0.9600 |
C5—C6 | 1.392 (3) | C16—H16C | 0.9600 |
C5—H5 | 0.9300 | C17—H17A | 0.9600 |
C7—C8 | 1.408 (2) | C17—H17B | 0.9600 |
C7—C12 | 1.429 (3) | C17—H17C | 0.9600 |
C8—C9 | 1.362 (3) | ||
C12—O3—H3 | 109.5 | C9—C10—H10 | 117.5 |
O2'—N1—O1' | 119.6 (10) | C10—C11—C12 | 116.78 (16) |
O2—N1—O1 | 126.8 (8) | C10—C11—C14 | 122.62 (17) |
O2'—N1—C1 | 118.1 (7) | C12—C11—C14 | 120.59 (16) |
O1'—N1—C1 | 122.2 (5) | O3—C12—C11 | 119.79 (16) |
O2—N1—C1 | 116.6 (5) | O3—C12—C7 | 120.99 (16) |
O1—N1—C1 | 116.4 (6) | C11—C12—C7 | 119.20 (15) |
N3—N2—C6 | 114.81 (15) | C9—C13—H13A | 109.5 |
N2—N3—C7 | 116.74 (15) | C9—C13—H13B | 109.5 |
C2—C1—C6 | 122.12 (19) | H13A—C13—H13B | 109.5 |
C2—C1—N1 | 116.10 (18) | C9—C13—H13C | 109.5 |
C6—C1—N1 | 121.77 (17) | H13A—C13—H13C | 109.5 |
C3—C2—C1 | 118.8 (2) | H13B—C13—H13C | 109.5 |
C3—C2—H2 | 120.6 | C17—C14—C16 | 111.1 (2) |
C1—C2—H2 | 120.6 | C17—C14—C11 | 109.2 (2) |
C2—C3—C4 | 120.94 (19) | C16—C14—C11 | 110.12 (19) |
C2—C3—Cl1 | 119.29 (17) | C17—C14—C15 | 107.7 (2) |
C4—C3—Cl1 | 119.75 (18) | C16—C14—C15 | 107.5 (2) |
C5—C4—C3 | 119.8 (2) | C11—C14—C15 | 111.17 (17) |
C5—C4—H4 | 120.1 | C14—C15—H15A | 109.5 |
C3—C4—H4 | 120.1 | C14—C15—H15B | 109.5 |
C4—C5—C6 | 121.11 (19) | H15A—C15—H15B | 109.5 |
C4—C5—H5 | 119.4 | C14—C15—H15C | 109.5 |
C6—C5—H5 | 119.4 | H15A—C15—H15C | 109.5 |
C5—C6—C1 | 117.11 (17) | H15B—C15—H15C | 109.5 |
C5—C6—N2 | 122.56 (17) | C14—C16—H16A | 109.5 |
C1—C6—N2 | 120.32 (17) | C14—C16—H16B | 109.5 |
N3—C7—C8 | 114.70 (16) | H16A—C16—H16B | 109.5 |
N3—C7—C12 | 124.97 (16) | C14—C16—H16C | 109.5 |
C8—C7—C12 | 120.30 (16) | H16A—C16—H16C | 109.5 |
C9—C8—C7 | 120.93 (17) | H16B—C16—H16C | 109.5 |
C9—C8—H8 | 119.5 | C14—C17—H17A | 109.5 |
C7—C8—H8 | 119.5 | C14—C17—H17B | 109.5 |
C8—C9—C10 | 117.79 (16) | H17A—C17—H17B | 109.5 |
C8—C9—C13 | 122.19 (17) | C14—C17—H17C | 109.5 |
C10—C9—C13 | 120.00 (17) | H17A—C17—H17C | 109.5 |
C11—C10—C9 | 124.95 (17) | H17B—C17—H17C | 109.5 |
C11—C10—H10 | 117.5 | ||
C6—N2—N3—C7 | −179.36 (15) | N2—N3—C7—C8 | 177.70 (16) |
O2'—N1—C1—C2 | 12 (2) | N2—N3—C7—C12 | −0.3 (3) |
O1'—N1—C1—C2 | −165.3 (16) | N3—C7—C8—C9 | −177.44 (18) |
O2—N1—C1—C2 | −32.9 (10) | C12—C7—C8—C9 | 0.7 (3) |
O1—N1—C1—C2 | 142.5 (11) | C7—C8—C9—C10 | −2.1 (3) |
O2'—N1—C1—C6 | −168 (2) | C7—C8—C9—C13 | 176.00 (19) |
O1'—N1—C1—C6 | 14.0 (16) | C8—C9—C10—C11 | 1.5 (3) |
O2—N1—C1—C6 | 146.4 (10) | C13—C9—C10—C11 | −176.6 (2) |
O1—N1—C1—C6 | −38.2 (11) | C9—C10—C11—C12 | 0.6 (3) |
C6—C1—C2—C3 | 0.7 (3) | C9—C10—C11—C14 | 179.5 (2) |
N1—C1—C2—C3 | −179.9 (2) | C10—C11—C12—O3 | 176.69 (19) |
C1—C2—C3—C4 | 1.4 (3) | C14—C11—C12—O3 | −2.2 (3) |
C1—C2—C3—Cl1 | −177.30 (16) | C10—C11—C12—C7 | −2.0 (3) |
C2—C3—C4—C5 | −2.0 (3) | C14—C11—C12—C7 | 179.05 (19) |
Cl1—C3—C4—C5 | 176.67 (17) | N3—C7—C12—O3 | 0.7 (3) |
C3—C4—C5—C6 | 0.5 (3) | C8—C7—C12—O3 | −177.22 (18) |
C4—C5—C6—C1 | 1.5 (3) | N3—C7—C12—C11 | 179.40 (18) |
C4—C5—C6—N2 | −177.41 (19) | C8—C7—C12—C11 | 1.5 (3) |
C2—C1—C6—C5 | −2.1 (3) | C10—C11—C14—C17 | −114.1 (2) |
N1—C1—C6—C5 | 178.6 (2) | C12—C11—C14—C17 | 64.7 (3) |
C2—C1—C6—N2 | 176.80 (19) | C10—C11—C14—C16 | 123.6 (2) |
N1—C1—C6—N2 | −2.5 (3) | C12—C11—C14—C16 | −57.5 (3) |
N3—N2—C6—C5 | 0.2 (3) | C10—C11—C14—C15 | 4.6 (3) |
N3—N2—C6—C1 | −178.68 (17) | C12—C11—C14—C15 | −176.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1′ | 0.82 | 2.28 | 2.933 (7) | 136 |
O3—H3···O1 | 0.82 | 2.50 | 3.142 (12) | 136 |
O3—H3···N2 | 0.82 | 1.84 | 2.553 (2) | 145 |
Experimental details
Crystal data | |
Chemical formula | C17H18ClN3O3 |
Mr | 347.79 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 14.578 (4), 7.0616 (19), 17.043 (5) |
β (°) | 101.233 (3) |
V (Å3) | 1720.9 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.31 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.930, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14642, 3927, 2563 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.141, 1.03 |
No. of reflections | 3927 |
No. of parameters | 241 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.26 |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1' | 0.82 | 2.28 | 2.933 (7) | 136.4 |
O3—H3···O1 | 0.82 | 2.50 | 3.142 (12) | 136.0 |
O3—H3···N2 | 0.82 | 1.84 | 2.553 (2) | 145.1 |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (20662007) and the Key Laboratory Open Foundation of Food Science of the Ministry of Education, Nanchang University (NCU200407).
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Benzotriazoles play an important role as a class of UV absorbers and have promising industrial applications (Ravichandran et al., 2002). N-oxides are a key type intermediates in the synthesis of benzotriazoles (Wen et al., 2006; Crawford, 1999) and the title compound is an important intermediate in the synthesis of 2-(2'-Hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chloro benzotriazole (UV 326), a good ultraviolet absorber. Due to the growing awareness of environmental protection, the demand for clean and 'green' (i.e solvent free) chemical syntheses has been growing, so using these synthetic methods to form intermediates have received attention (Tanaka & Toda, 2000). Herein we report a 'green' synthetic method and the crystal structure of the title compound. In the title moleclue (Fig .1) the dihedral angle between the two benzene rings is 1.03 (7)°. The overall conformation of the molecule is influenced, in part, by electron delocalization and by intramolecular O—H···O and O—H···N hydrogen bonds.