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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o13.
Published online 2009 December 4. doi:  10.1107/S1600536809050442
PMCID: PMC2980092

(E)-1-(1H-Benzotriazol-1-yl 3-oxide)-3-methoxy­but-2-en-1-one

Abstract

The title compound, C11H11N3O3, crystallizes with two independent mol­ecules of similar geometry in the asymmetric unit. The mol­ecular conformations are stabilized by intra­molecular C—H(...)O hydrogen bonds. The crystal packing consists of wave-like layers parallel to the bc plane formed by inter­molecular C—H(...)O hydrogen-bonding inter­actions involving only one independent mol­ecule.

Related literature

For related structures, see: Barlos et al. (1985 [triangle]); Singh et al. (1988 [triangle]). For details of the biological activity of benzentriazol-containing compounds, see: Zhang et al. (2002 [triangle]). For comparative bond lengths, see: Allen et al. (1987 [triangle]).

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Object name is e-66-00o13-scheme1.jpg

Experimental

Crystal data

  • C11H11N3O3
  • M r = 233.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o13-efi1.jpg
  • a = 14.011 (3) Å
  • b = 10.014 (2) Å
  • c = 15.699 (3) Å
  • β = 100.13 (3)°
  • V = 2168.3 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 173 K
  • 0.40 × 0.40 × 0.30 mm

Data collection

  • Rigaku Mercury CCD/AFC diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 [triangle]) T min = 0.959, T max = 0.969
  • 15367 measured reflections
  • 3771 independent reflections
  • 3564 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.141
  • S = 1.17
  • 3771 reflections
  • 308 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2007 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050442/rz2397sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050442/rz2397Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Benzotriazole derivatives exhibit good pharmacological activities and a wide spectrum of biological activities (Zhang et al., 2002). In order to search for new benzotriazole compounds with higher bioactivity, we synthesized the title compound and describe its structure here.

The asymmetric unit of the title compound (Fig. 1) contains two independent molecules of similar geometry. The molecules are almost planar, the maximum deviation being 0.110 (2) Å for atom O2 in one molecule and 0.093 (3) Å for atom C22 in the other molecule. All bond lengths in the molecules are normal (Allen et al., 1987) and in a good agreement with those reported previously for related compound (Barlos et al., 1985; Singh et al., 1988). The molecular conformations are stabilized by intramolecular C—H···O hydrogen bonds (Table 1). In the crystal packing, molecules containing the N4–N6 nitrogen atoms are linked by intermolecular C—H···O hydrogen bonds to form wavy layers parallel to the bc plane intersecting each other.

Experimental

3-Methoxycrotonic acid (20 mmol) was dissolved in dichloromethane and cooled to 273 K, then 1-hydroxybenzotriazole (30 mmol) was added in one portion. After 10 h stirring at room temperature, the solution was washed successively with 1 N HCl and saturated NaCl, and the organic layer was separated, dried with Na2SO4 and evaporated to obtain the primary product. The pure compound was isolated by column chromatography (3.4 g, yield 73%). Single crystals suitable for X-ray measurements were obtained by slow evaporation of an ethyl acetate solution at room temperature. 1H NMR (400 MHz, CDCl3) δ: 8.49 (d, J = 8 Hz, 1H), 7.99 (d, J = 8 Hz, 1H), 7.75 (t, 1H), 7.53 (t, 1H), 6.30 (s, 1H), 3.85 (s, 3H), 2.50 (s, 3H).

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, with atom-labelling scheme and 40% probability displacement ellipsoids.

Crystal data

C11H11N3O3F(000) = 976
Mr = 233.23Dx = 1.429 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6607 reflections
a = 14.011 (3) Åθ = 1.3–27.5°
b = 10.014 (2) ŵ = 0.11 mm1
c = 15.699 (3) ÅT = 173 K
β = 100.13 (3)°Block, colourless
V = 2168.3 (8) Å30.40 × 0.40 × 0.30 mm
Z = 8

Data collection

Rigaku Mercury CCD/AFC diffractometer3771 independent reflections
Radiation source: Sealed Tube3564 reflections with I > 2σ(I)
Graphite MonochromatorRint = 0.050
[var phi] and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)h = −11→16
Tmin = 0.959, Tmax = 0.969k = −11→11
15367 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.141w = 1/[σ2(Fo2) + (0.047P)2 + 1.4328P] where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max < 0.001
3771 reflectionsΔρmax = 0.36 e Å3
308 parametersΔρmin = −0.28 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0028 (7)

Special details

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)

xyzUiso*/Ueq
O10.05575 (14)1.36306 (16)−0.08605 (11)0.0400 (5)
O20.14314 (14)0.85371 (17)0.05299 (11)0.0411 (5)
O30.18500 (13)0.72121 (18)−0.19749 (12)0.0436 (5)
O40.45305 (13)−0.36283 (16)−0.08904 (11)0.0387 (4)
O50.33528 (13)0.14842 (17)−0.00327 (10)0.0383 (4)
O60.32908 (13)0.26568 (17)−0.26560 (11)0.0380 (4)
N10.07616 (14)1.25933 (19)−0.03951 (12)0.0297 (5)
N20.09586 (14)1.14406 (18)−0.07177 (12)0.0292 (4)
N30.11216 (14)1.05828 (19)−0.00260 (11)0.0272 (4)
N40.43065 (14)−0.25590 (19)−0.05301 (12)0.0282 (4)
N50.40993 (14)−0.14465 (19)−0.09592 (12)0.0286 (4)
N60.38814 (13)−0.05422 (19)−0.03598 (11)0.0264 (4)
C10.10201 (16)1.1226 (2)0.07363 (14)0.0278 (5)
C20.10832 (17)1.0824 (3)0.15936 (15)0.0341 (6)
H2B0.12370.99320.17730.041*
C30.09079 (18)1.1801 (3)0.21672 (15)0.0375 (6)
H3A0.09401.15660.27580.045*
C40.06852 (18)1.3119 (3)0.19175 (16)0.0377 (6)
H4A0.05741.37480.23430.045*
C50.06218 (17)1.3534 (2)0.10725 (16)0.0337 (6)
H5B0.04731.44280.08950.040*
C60.07931 (16)1.2541 (2)0.05007 (14)0.0280 (5)
C70.13675 (16)0.9212 (2)−0.01186 (15)0.0286 (5)
C80.15008 (16)0.8828 (2)−0.09752 (15)0.0302 (5)
H8A0.14170.9484−0.14190.036*
C90.17412 (17)0.7568 (2)−0.11732 (16)0.0336 (6)
C100.1935 (2)0.6417 (3)−0.0578 (2)0.0485 (7)
H10A0.20910.5631−0.09000.073*
H10B0.13580.6232−0.03230.073*
H10C0.24820.6625−0.01180.073*
C110.1690 (2)0.8191 (3)−0.26569 (18)0.0473 (7)
H11A0.17970.7781−0.31990.071*
H11B0.21430.8937−0.25090.071*
H11C0.10230.8522−0.27260.071*
C120.39549 (16)−0.1127 (2)0.04485 (14)0.0271 (5)
C130.38077 (17)−0.0679 (3)0.12604 (15)0.0326 (6)
H13A0.36130.02110.13500.039*
C140.39604 (18)−0.1599 (3)0.19193 (16)0.0368 (6)
H14A0.3867−0.13290.24790.044*
C150.42483 (18)−0.2921 (3)0.18018 (16)0.0367 (6)
H15A0.4350−0.35130.22820.044*
C160.43866 (17)−0.3378 (2)0.10031 (15)0.0333 (6)
H16A0.4572−0.42710.09110.040*
C170.42345 (16)−0.2437 (2)0.03457 (14)0.0273 (5)
C180.35556 (16)0.0780 (2)−0.06071 (15)0.0293 (5)
C190.35254 (16)0.1095 (2)−0.15081 (15)0.0289 (5)
H19A0.36580.0412−0.18910.035*
C200.33127 (17)0.2343 (2)−0.18219 (15)0.0307 (5)
C210.3085 (2)0.3529 (2)−0.13222 (18)0.0404 (6)
H21A0.29600.4300−0.17100.061*
H21B0.36370.3723−0.08620.061*
H21C0.25100.3344−0.10660.061*
C220.3452 (2)0.1631 (3)−0.32498 (16)0.0415 (6)
H22A0.34130.2015−0.38290.062*
H22B0.29570.0936−0.32650.062*
H22C0.40960.1240−0.30620.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0628 (12)0.0248 (9)0.0349 (9)0.0044 (8)0.0158 (9)0.0052 (8)
O20.0557 (12)0.0323 (10)0.0359 (10)0.0058 (8)0.0098 (8)0.0062 (8)
O30.0470 (11)0.0364 (10)0.0493 (11)−0.0006 (8)0.0138 (9)−0.0164 (9)
O40.0562 (11)0.0268 (9)0.0349 (9)0.0079 (8)0.0128 (8)−0.0030 (7)
O50.0519 (11)0.0336 (9)0.0302 (9)0.0057 (8)0.0090 (8)−0.0069 (8)
O60.0448 (10)0.0327 (10)0.0388 (10)0.0074 (8)0.0132 (8)0.0094 (8)
N10.0380 (11)0.0234 (10)0.0289 (10)−0.0006 (8)0.0090 (9)−0.0008 (8)
N20.0380 (11)0.0235 (10)0.0266 (10)−0.0004 (8)0.0075 (8)0.0001 (8)
N30.0335 (11)0.0257 (10)0.0231 (9)0.0003 (8)0.0066 (8)0.0001 (8)
N40.0330 (11)0.0247 (10)0.0279 (10)0.0001 (8)0.0082 (8)0.0003 (8)
N50.0352 (11)0.0260 (10)0.0255 (10)0.0011 (8)0.0078 (8)−0.0011 (8)
N60.0306 (10)0.0257 (10)0.0232 (9)−0.0003 (8)0.0054 (8)−0.0001 (8)
C10.0260 (12)0.0314 (13)0.0264 (12)−0.0019 (10)0.0057 (9)−0.0021 (10)
C20.0334 (13)0.0417 (14)0.0271 (12)0.0033 (11)0.0050 (10)0.0032 (11)
C30.0367 (14)0.0526 (16)0.0235 (12)−0.0021 (12)0.0063 (10)−0.0025 (11)
C40.0358 (13)0.0477 (16)0.0301 (13)−0.0028 (12)0.0073 (11)−0.0125 (12)
C50.0331 (13)0.0307 (13)0.0376 (13)−0.0031 (10)0.0068 (11)−0.0073 (11)
C60.0310 (12)0.0288 (12)0.0246 (11)−0.0039 (10)0.0056 (10)−0.0026 (10)
C70.0272 (12)0.0248 (12)0.0341 (13)−0.0010 (9)0.0066 (10)0.0006 (10)
C80.0305 (12)0.0269 (12)0.0334 (13)−0.0014 (10)0.0064 (10)−0.0017 (10)
C90.0276 (12)0.0302 (13)0.0433 (14)−0.0027 (10)0.0073 (11)−0.0075 (11)
C100.0504 (17)0.0285 (14)0.0657 (19)0.0052 (12)0.0080 (15)−0.0031 (13)
C110.0534 (17)0.0480 (17)0.0427 (15)−0.0070 (14)0.0149 (13)−0.0159 (13)
C120.0250 (11)0.0314 (13)0.0243 (11)−0.0047 (9)0.0029 (9)0.0002 (10)
C130.0374 (13)0.0348 (13)0.0265 (12)−0.0012 (11)0.0085 (10)−0.0040 (10)
C140.0387 (14)0.0459 (15)0.0267 (12)−0.0043 (12)0.0084 (11)−0.0023 (11)
C150.0402 (14)0.0419 (15)0.0285 (12)−0.0060 (12)0.0073 (11)0.0068 (11)
C160.0334 (13)0.0321 (13)0.0343 (13)−0.0046 (10)0.0060 (11)0.0032 (11)
C170.0290 (12)0.0296 (12)0.0235 (11)−0.0043 (9)0.0049 (9)−0.0016 (9)
C180.0281 (12)0.0259 (12)0.0332 (13)−0.0009 (9)0.0035 (10)−0.0028 (10)
C190.0313 (12)0.0269 (12)0.0285 (12)−0.0010 (10)0.0047 (10)−0.0013 (10)
C200.0277 (12)0.0312 (13)0.0344 (13)0.0002 (10)0.0085 (10)0.0023 (10)
C210.0433 (15)0.0274 (13)0.0523 (16)0.0035 (11)0.0131 (13)0.0013 (12)
C220.0553 (17)0.0390 (15)0.0317 (13)0.0053 (12)0.0118 (12)0.0062 (11)

Geometric parameters (Å, °)

O1—N11.273 (2)C8—C91.356 (3)
O2—C71.212 (3)C8—H8A0.9500
O3—C91.342 (3)C9—C101.478 (4)
O3—C111.440 (3)C10—H10A0.9800
O4—N41.276 (2)C10—H10B0.9800
O5—C181.217 (3)C10—H10C0.9800
O6—C201.342 (3)C11—H11A0.9800
O6—C221.431 (3)C11—H11B0.9800
N1—N21.309 (3)C11—H11C0.9800
N1—C61.400 (3)C12—C171.386 (3)
N2—N31.372 (3)C12—C131.400 (3)
N3—C11.388 (3)C13—C141.373 (3)
N3—C71.429 (3)C13—H13A0.9500
N4—N51.308 (3)C14—C151.406 (4)
N4—C171.401 (3)C14—H14A0.9500
N5—N61.378 (3)C15—C161.380 (3)
N6—C121.385 (3)C15—H15A0.9500
N6—C181.432 (3)C16—C171.385 (3)
C1—C61.389 (3)C16—H16A0.9500
C1—C21.393 (3)C18—C191.442 (3)
C2—C31.381 (4)C19—C201.357 (3)
C2—H2B0.9500C19—H19A0.9500
C3—C41.396 (4)C20—C211.488 (3)
C3—H3A0.9500C21—H21A0.9800
C4—C51.378 (4)C21—H21B0.9800
C4—H4A0.9500C21—H21C0.9800
C5—C61.389 (3)C22—H22A0.9800
C5—H5B0.9500C22—H22B0.9800
C7—C81.442 (3)C22—H22C0.9800
C9—O3—C11119.2 (2)H10A—C10—H10C109.5
C20—O6—C22119.25 (19)H10B—C10—H10C109.5
O1—N1—N2122.60 (18)O3—C11—H11A109.5
O1—N1—C6124.83 (19)O3—C11—H11B109.5
N2—N1—C6112.57 (18)H11A—C11—H11B109.5
N1—N2—N3105.25 (17)O3—C11—H11C109.5
N2—N3—C1111.34 (18)H11A—C11—H11C109.5
N2—N3—C7122.05 (18)H11B—C11—H11C109.5
C1—N3—C7126.62 (19)N6—C12—C17105.70 (19)
O4—N4—N5122.44 (18)N6—C12—C13134.4 (2)
O4—N4—C17125.01 (19)C17—C12—C13119.9 (2)
N5—N4—C17112.55 (18)C14—C13—C12116.2 (2)
N4—N5—N6105.29 (16)C14—C13—H13A121.9
N5—N6—C12110.97 (18)C12—C13—H13A121.9
N5—N6—C18121.38 (18)C13—C14—C15122.9 (2)
C12—N6—C18127.49 (19)C13—C14—H14A118.6
N3—C1—C6105.28 (19)C15—C14—H14A118.6
N3—C1—C2134.4 (2)C16—C15—C14121.4 (2)
C6—C1—C2120.3 (2)C16—C15—H15A119.3
C3—C2—C1115.9 (2)C14—C15—H15A119.3
C3—C2—H2B122.0C15—C16—C17115.1 (2)
C1—C2—H2B122.0C15—C16—H16A122.5
C2—C3—C4122.9 (2)C17—C16—H16A122.5
C2—C3—H3A118.5C16—C17—C12124.5 (2)
C4—C3—H3A118.5C16—C17—N4130.1 (2)
C5—C4—C3121.9 (2)C12—C17—N4105.49 (19)
C5—C4—H4A119.0O5—C18—N6116.1 (2)
C3—C4—H4A119.0O5—C18—C19129.0 (2)
C4—C5—C6114.7 (2)N6—C18—C19114.9 (2)
C4—C5—H5B122.7C20—C19—C18121.6 (2)
C6—C5—H5B122.7C20—C19—H19A119.2
C5—C6—C1124.3 (2)C18—C19—H19A119.2
C5—C6—N1130.1 (2)O6—C20—C19122.4 (2)
C1—C6—N1105.56 (19)O6—C20—C21111.0 (2)
O2—C7—N3115.7 (2)C19—C20—C21126.7 (2)
O2—C7—C8129.2 (2)C20—C21—H21A109.5
N3—C7—C8115.1 (2)C20—C21—H21B109.5
C9—C8—C7122.7 (2)H21A—C21—H21B109.5
C9—C8—H8A118.7C20—C21—H21C109.5
C7—C8—H8A118.7H21A—C21—H21C109.5
O3—C9—C8122.4 (2)H21B—C21—H21C109.5
O3—C9—C10110.3 (2)O6—C22—H22A109.5
C8—C9—C10127.3 (2)O6—C22—H22B109.5
C9—C10—H10A109.5H22A—C22—H22B109.5
C9—C10—H10B109.5O6—C22—H22C109.5
H10A—C10—H10B109.5H22A—C22—H22C109.5
C9—C10—H10C109.5H22B—C22—H22C109.5
O1—N1—N2—N3−179.03 (19)C11—O3—C9—C8−1.1 (3)
C6—N1—N2—N30.4 (2)C11—O3—C9—C10179.8 (2)
N1—N2—N3—C10.1 (2)C7—C8—C9—O3179.0 (2)
N1—N2—N3—C7−179.59 (19)C7—C8—C9—C10−2.1 (4)
O4—N4—N5—N6178.92 (19)N5—N6—C12—C170.4 (2)
C17—N4—N5—N60.1 (2)C18—N6—C12—C17175.7 (2)
N4—N5—N6—C12−0.3 (2)N5—N6—C12—C13−179.2 (2)
N4—N5—N6—C18−175.93 (19)C18—N6—C12—C13−3.9 (4)
N2—N3—C1—C6−0.5 (2)N6—C12—C13—C14179.9 (2)
C7—N3—C1—C6179.1 (2)C17—C12—C13—C140.3 (3)
N2—N3—C1—C2178.3 (2)C12—C13—C14—C150.0 (4)
C7—N3—C1—C2−2.0 (4)C13—C14—C15—C16−0.6 (4)
N3—C1—C2—C3−178.7 (2)C14—C15—C16—C170.9 (3)
C6—C1—C2—C30.0 (3)C15—C16—C17—C12−0.6 (3)
C1—C2—C3—C4−0.4 (4)C15—C16—C17—N4−179.8 (2)
C2—C3—C4—C50.3 (4)N6—C12—C17—C16−179.7 (2)
C3—C4—C5—C60.2 (4)C13—C12—C17—C160.0 (4)
C4—C5—C6—C1−0.5 (4)N6—C12—C17—N4−0.3 (2)
C4—C5—C6—N1177.9 (2)C13—C12—C17—N4179.4 (2)
N3—C1—C6—C5179.5 (2)O4—N4—C17—C160.7 (4)
C2—C1—C6—C50.4 (4)N5—N4—C17—C16179.5 (2)
N3—C1—C6—N10.7 (2)O4—N4—C17—C12−178.6 (2)
C2—C1—C6—N1−178.3 (2)N5—N4—C17—C120.2 (3)
O1—N1—C6—C50.0 (4)N5—N6—C18—O5177.7 (2)
N2—N1—C6—C5−179.4 (2)C12—N6—C18—O52.8 (3)
O1—N1—C6—C1178.7 (2)N5—N6—C18—C19−3.0 (3)
N2—N1—C6—C1−0.7 (3)C12—N6—C18—C19−177.9 (2)
N2—N3—C7—O2−175.4 (2)O5—C18—C19—C205.0 (4)
C1—N3—C7—O25.0 (3)N6—C18—C19—C20−174.2 (2)
N2—N3—C7—C84.4 (3)C22—O6—C20—C193.0 (3)
C1—N3—C7—C8−175.3 (2)C22—O6—C20—C21−177.4 (2)
O2—C7—C8—C9−0.7 (4)C18—C19—C20—O6179.3 (2)
N3—C7—C8—C9179.6 (2)C18—C19—C20—C21−0.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2B···O20.952.452.925 (3)111
C13—H13A···O50.952.492.961 (3)111
C14—H14A···O4i0.952.573.398 (3)147
C16—H16A···O4ii0.952.453.379 (3)165

Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+1, −y−1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2397).

References

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