organic compounds
1-Benzyl-1H-benzotriazole 3-oxide–1-hydroxy-1H-benzotriazole (1/1)
aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamilnadu, India, bDepartment of Physics, Sethupathy Government Arts College, Ramanathapuram 623 502, Tamilnadu, India, and cInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: b_ravidurai@yahoo.com
In the title compound, C6H5N3O·C13H11N3O, the benzotriazole ring system in the 1-benzyl-1H-benzotriazole 3-oxide (A) molecule is close to being planar (r.m.s. deviation = 0.011 Å); its mean plane forms a dihedral angle of 67.56 (7)° with that of the attached phenyl ring. The benzotriazole ring system in the 1-hydroxybenzotriazole (B) molecule is also close to being planar (r.m.s. deviation = 0.010 Å). In the crystal, weak C—H⋯O and C—H⋯π interactions are present. The A and B molecules are linked by an O—H⋯N hydrogen bond.
Related literature
For related structures and background to benzotriazoles, see: Ravindran et al. (2009); Selvarathy Grace et al. (2012).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994); 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: PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812030061/hb6878sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030061/hb6878Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812030061/hb6878Isup3.cml
A mixture of the sodium salt of 1- hydroxyl benzotriazole (0.314 g, 2 mmol) and benzyl chloride (0.126 g, 1 mmol) in methanol (10 ml), were heated at 333K with stirring for 6 hours. The mixture was kept aside for slow evaporation. After a week, colourless blocks were recovered.
H atoms were positioned geometrically [C—H = 0.95 (aromatic) or 0.99 Å (methylene)] and refined using a riding model, with Uiso(H) = 1.2Ueq(C).
As part of our ongoing studies of benzotriazole derivatives (Ravindran et al., 2009; Selvarathy Grace et al., 2012), we now report the
of the title compound (I), (Fig. 1).The benzotriazole rings are essentially planar with the maximum deviation from planarity being 0.015 (14) Å for atoms N1 and N5. The mean plane of the benzotriazole ring N1—N3/C1—C6 forms a dihedral angle of 67.56 (7) Å with the mean plane of the phenyl ring (C8—C13).
The crystal packing features weak C—H···π interactions. The hydrogen bonding interactions are shown in Fig 2.
For related structures and background to benzotriazoles, see: Ravindran et al. (2009); Selvarathy Grace et al. (2012).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994); 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: PLATON (Spek, 2009).C6H5N3O·C13H11N3O | F(000) = 752 |
Mr = 360.38 | Dx = 1.419 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 11.2728 (8) Å | θ = 65–69° |
b = 12.2354 (5) Å | µ = 0.80 mm−1 |
c = 13.1002 (9) Å | T = 193 K |
β = 110.946 (3)° | Block, colourless |
V = 1687.47 (18) Å3 | 0.40 × 0.40 × 0.30 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.102 |
Radiation source: rotating anode | θmax = 70.0°, θmin = 4.2° |
Graphite monochromator | h = 0→13 |
ω/2θ scans | k = 0→14 |
3364 measured reflections | l = −15→14 |
3197 independent reflections | 3 standard reflections every 60 min |
2980 reflections with I > 2σ(I) | intensity decay: 2% |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0776P)2 + 0.6089P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
3197 reflections | Δρmax = 0.35 e Å−3 |
245 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0035 (5) |
C6H5N3O·C13H11N3O | V = 1687.47 (18) Å3 |
Mr = 360.38 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 11.2728 (8) Å | µ = 0.80 mm−1 |
b = 12.2354 (5) Å | T = 193 K |
c = 13.1002 (9) Å | 0.40 × 0.40 × 0.30 mm |
β = 110.946 (3)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.102 |
3364 measured reflections | 3 standard reflections every 60 min |
3197 independent reflections | intensity decay: 2% |
2980 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.35 e Å−3 |
3197 reflections | Δρmin = −0.27 e Å−3 |
245 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
N1 | 0.23017 (11) | 0.44814 (10) | 0.07382 (10) | 0.0233 (3) | |
N2 | 0.21688 (11) | 0.34031 (10) | 0.08272 (10) | 0.0261 (3) | |
N3 | 0.12730 (11) | 0.32935 (10) | 0.12460 (10) | 0.0256 (3) | |
C1 | 0.08113 (13) | 0.42800 (12) | 0.14320 (11) | 0.0231 (3) | |
C2 | −0.01438 (14) | 0.45549 (14) | 0.18361 (13) | 0.0314 (4) | |
H2 | −0.0618 | 0.4017 | 0.2048 | 0.038* | |
C3 | −0.03466 (15) | 0.56486 (15) | 0.19043 (13) | 0.0351 (4) | |
H3 | −0.0985 | 0.5880 | 0.2172 | 0.042* | |
C4 | 0.03627 (15) | 0.64472 (14) | 0.15895 (13) | 0.0340 (4) | |
H4 | 0.0191 | 0.7197 | 0.1663 | 0.041* | |
C5 | 0.12920 (14) | 0.61800 (12) | 0.11806 (13) | 0.0284 (3) | |
H5 | 0.1760 | 0.6719 | 0.0963 | 0.034* | |
C6 | 0.15024 (13) | 0.50592 (11) | 0.11070 (11) | 0.0216 (3) | |
C7 | 0.32424 (14) | 0.48951 (13) | 0.02917 (12) | 0.0285 (3) | |
H7A | 0.2976 | 0.5627 | −0.0030 | 0.034* | |
H7B | 0.3269 | 0.4402 | −0.0299 | 0.034* | |
C8 | 0.45521 (13) | 0.49730 (12) | 0.11541 (12) | 0.0250 (3) | |
C9 | 0.50482 (15) | 0.59795 (13) | 0.15887 (14) | 0.0327 (4) | |
H9 | 0.4566 | 0.6626 | 0.1333 | 0.039* | |
C10 | 0.62432 (17) | 0.60451 (15) | 0.23944 (15) | 0.0384 (4) | |
H10 | 0.6576 | 0.6736 | 0.2691 | 0.046* | |
C11 | 0.69520 (15) | 0.51109 (15) | 0.27686 (13) | 0.0368 (4) | |
H11 | 0.7768 | 0.5158 | 0.3326 | 0.044* | |
C12 | 0.64695 (16) | 0.41032 (15) | 0.23292 (15) | 0.0379 (4) | |
H12 | 0.6957 | 0.3459 | 0.2583 | 0.045* | |
C13 | 0.52801 (15) | 0.40353 (13) | 0.15226 (14) | 0.0323 (4) | |
H13 | 0.4957 | 0.3345 | 0.1217 | 0.039* | |
O1 | 0.09227 (11) | 0.23257 (9) | 0.14562 (11) | 0.0383 (3) | |
N4 | 0.66756 (14) | 0.18397 (12) | 0.08895 (14) | 0.0428 (4) | |
N5 | 0.75634 (14) | 0.21667 (11) | 0.05304 (14) | 0.0417 (4) | |
N6 | 0.81861 (13) | 0.12778 (10) | 0.03929 (12) | 0.0312 (3) | |
C14 | 0.77039 (14) | 0.03437 (12) | 0.06416 (12) | 0.0252 (3) | |
C15 | 0.79910 (16) | −0.07638 (13) | 0.06063 (13) | 0.0329 (4) | |
H15 | 0.8655 | −0.1009 | 0.0377 | 0.039* | |
C16 | 0.72455 (18) | −0.14724 (13) | 0.09268 (14) | 0.0372 (4) | |
H16 | 0.7400 | −0.2235 | 0.0921 | 0.045* | |
C17 | 0.62562 (17) | −0.11034 (15) | 0.12655 (14) | 0.0378 (4) | |
H17 | 0.5768 | −0.1625 | 0.1482 | 0.045* | |
C18 | 0.59823 (16) | −0.00226 (15) | 0.12905 (14) | 0.0353 (4) | |
H18 | 0.5313 | 0.0218 | 0.1516 | 0.042* | |
C19 | 0.67306 (15) | 0.07221 (13) | 0.09693 (13) | 0.0293 (3) | |
O2 | 0.91290 (12) | 0.13654 (10) | −0.00258 (11) | 0.0419 (3) | |
H2A | 0.9753 | 0.1692 | 0.0424 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0237 (6) | 0.0214 (6) | 0.0286 (6) | −0.0013 (5) | 0.0138 (5) | 0.0007 (5) |
N2 | 0.0253 (6) | 0.0211 (6) | 0.0344 (7) | −0.0006 (5) | 0.0139 (5) | −0.0006 (5) |
N3 | 0.0235 (6) | 0.0201 (6) | 0.0339 (7) | −0.0012 (4) | 0.0112 (5) | 0.0047 (5) |
C1 | 0.0217 (6) | 0.0232 (7) | 0.0246 (7) | 0.0012 (5) | 0.0086 (5) | 0.0035 (5) |
C2 | 0.0267 (7) | 0.0391 (9) | 0.0321 (8) | 0.0020 (6) | 0.0150 (6) | 0.0055 (7) |
C3 | 0.0309 (8) | 0.0452 (10) | 0.0327 (8) | 0.0095 (7) | 0.0157 (7) | −0.0010 (7) |
C4 | 0.0361 (8) | 0.0288 (8) | 0.0355 (8) | 0.0080 (6) | 0.0109 (7) | −0.0055 (6) |
C5 | 0.0311 (8) | 0.0215 (7) | 0.0322 (8) | −0.0004 (6) | 0.0108 (6) | 0.0006 (6) |
C6 | 0.0210 (6) | 0.0215 (7) | 0.0226 (7) | 0.0002 (5) | 0.0081 (5) | 0.0004 (5) |
C7 | 0.0290 (8) | 0.0327 (8) | 0.0294 (8) | −0.0041 (6) | 0.0173 (6) | 0.0016 (6) |
C8 | 0.0264 (7) | 0.0273 (7) | 0.0280 (7) | −0.0023 (6) | 0.0179 (6) | 0.0000 (6) |
C9 | 0.0350 (8) | 0.0258 (8) | 0.0426 (9) | −0.0038 (6) | 0.0203 (7) | 0.0017 (6) |
C10 | 0.0405 (9) | 0.0372 (9) | 0.0416 (9) | −0.0148 (7) | 0.0197 (7) | −0.0068 (7) |
C11 | 0.0292 (8) | 0.0537 (11) | 0.0301 (8) | −0.0065 (7) | 0.0138 (6) | 0.0012 (7) |
C12 | 0.0342 (8) | 0.0414 (9) | 0.0415 (9) | 0.0066 (7) | 0.0177 (7) | 0.0076 (7) |
C13 | 0.0334 (8) | 0.0287 (8) | 0.0407 (9) | 0.0001 (6) | 0.0206 (7) | −0.0030 (6) |
O1 | 0.0371 (6) | 0.0216 (6) | 0.0573 (8) | −0.0058 (4) | 0.0181 (5) | 0.0105 (5) |
N4 | 0.0421 (8) | 0.0264 (7) | 0.0647 (10) | 0.0033 (6) | 0.0249 (7) | −0.0049 (7) |
N5 | 0.0449 (8) | 0.0207 (7) | 0.0623 (10) | 0.0006 (6) | 0.0225 (7) | 0.0008 (6) |
N6 | 0.0332 (7) | 0.0223 (6) | 0.0432 (8) | −0.0021 (5) | 0.0199 (6) | 0.0021 (5) |
C14 | 0.0301 (7) | 0.0211 (7) | 0.0261 (7) | −0.0034 (6) | 0.0121 (6) | −0.0010 (5) |
C15 | 0.0427 (9) | 0.0258 (8) | 0.0357 (8) | 0.0037 (7) | 0.0208 (7) | −0.0014 (6) |
C16 | 0.0550 (11) | 0.0203 (7) | 0.0382 (9) | −0.0034 (7) | 0.0189 (8) | −0.0006 (6) |
C17 | 0.0452 (10) | 0.0367 (9) | 0.0342 (9) | −0.0141 (7) | 0.0175 (7) | 0.0008 (7) |
C18 | 0.0343 (8) | 0.0419 (9) | 0.0350 (9) | −0.0054 (7) | 0.0187 (7) | −0.0043 (7) |
C19 | 0.0313 (8) | 0.0247 (8) | 0.0327 (8) | 0.0001 (6) | 0.0124 (6) | −0.0043 (6) |
O2 | 0.0451 (7) | 0.0395 (7) | 0.0521 (7) | −0.0101 (5) | 0.0309 (6) | −0.0005 (6) |
N1—N2 | 1.3376 (17) | C10—H10 | 0.9500 |
N1—C6 | 1.3625 (18) | C11—C12 | 1.387 (3) |
N1—C7 | 1.4718 (17) | C11—H11 | 0.9500 |
N2—N3 | 1.3171 (17) | C12—C13 | 1.381 (2) |
N3—O1 | 1.3082 (16) | C12—H12 | 0.9500 |
N3—C1 | 1.3703 (19) | C13—H13 | 0.9500 |
C1—C6 | 1.391 (2) | N4—N5 | 1.311 (2) |
C1—C2 | 1.400 (2) | N4—C19 | 1.371 (2) |
C2—C3 | 1.366 (2) | N5—N6 | 1.3411 (19) |
C2—H2 | 0.9500 | N6—C14 | 1.3545 (19) |
C3—C4 | 1.414 (3) | N6—O2 | 1.3635 (17) |
C3—H3 | 0.9500 | C14—C19 | 1.393 (2) |
C4—C5 | 1.376 (2) | C14—C15 | 1.398 (2) |
C4—H4 | 0.9500 | C15—C16 | 1.373 (2) |
C5—C6 | 1.401 (2) | C15—H15 | 0.9500 |
C5—H5 | 0.9500 | C16—C17 | 1.414 (3) |
C7—H7A | 0.9900 | C16—H16 | 0.9500 |
C7—H7B | 0.9900 | C17—C18 | 1.361 (3) |
C8—C9 | 1.388 (2) | C17—H17 | 0.9500 |
C8—C13 | 1.393 (2) | C18—C19 | 1.404 (2) |
C9—H9 | 0.9500 | C18—H18 | 0.9500 |
C10—C11 | 1.380 (3) | O2—H2A | 0.8400 |
N2—N1—C6 | 111.83 (11) | C11—C10—C9 | 120.30 (16) |
N2—N1—C7 | 119.53 (12) | C11—C10—H10 | 119.9 |
C6—N1—C7 | 128.63 (12) | C9—C10—H10 | 119.9 |
N3—N2—N1 | 105.26 (11) | C10—C11—C12 | 119.83 (16) |
O1—N3—N2 | 120.92 (12) | C10—C11—H11 | 120.1 |
O1—N3—C1 | 126.69 (12) | C12—C11—H11 | 120.1 |
N2—N3—C1 | 112.38 (12) | C13—C12—C11 | 120.02 (16) |
N3—C1—C6 | 105.04 (12) | C13—C12—H12 | 120.0 |
N3—C1—C2 | 132.16 (14) | C11—C12—H12 | 120.0 |
C6—C1—C2 | 122.80 (14) | C12—C13—C8 | 120.41 (15) |
C3—C2—C1 | 115.44 (15) | C12—C13—H13 | 119.8 |
C3—C2—H2 | 122.3 | C8—C13—H13 | 119.8 |
C1—C2—H2 | 122.3 | N5—N4—C19 | 108.20 (14) |
C2—C3—C4 | 122.17 (15) | N4—N5—N6 | 107.69 (13) |
C2—C3—H3 | 118.9 | N5—N6—C14 | 112.19 (13) |
C4—C3—H3 | 118.9 | N5—N6—O2 | 120.74 (13) |
C5—C4—C3 | 122.55 (15) | C14—N6—O2 | 126.92 (13) |
C5—C4—H4 | 118.7 | N6—C14—C19 | 102.81 (13) |
C3—C4—H4 | 118.7 | N6—C14—C15 | 133.83 (14) |
C4—C5—C6 | 115.51 (14) | C19—C14—C15 | 123.35 (14) |
C4—C5—H5 | 122.2 | C16—C15—C14 | 115.32 (15) |
C6—C5—H5 | 122.2 | C16—C15—H15 | 122.3 |
N1—C6—C1 | 105.47 (12) | C14—C15—H15 | 122.3 |
N1—C6—C5 | 133.00 (14) | C15—C16—C17 | 122.14 (15) |
C1—C6—C5 | 121.52 (13) | C15—C16—H16 | 118.9 |
N1—C7—C8 | 112.06 (12) | C17—C16—H16 | 118.9 |
N1—C7—H7A | 109.2 | C18—C17—C16 | 121.94 (16) |
C8—C7—H7A | 109.2 | C18—C17—H17 | 119.0 |
N1—C7—H7B | 109.2 | C16—C17—H17 | 119.0 |
C8—C7—H7B | 109.2 | C17—C18—C19 | 117.22 (15) |
H7A—C7—H7B | 107.9 | C17—C18—H18 | 121.4 |
C9—C8—C13 | 119.20 (14) | C19—C18—H18 | 121.4 |
C9—C8—C7 | 120.43 (14) | N4—C19—C14 | 109.10 (14) |
C13—C8—C7 | 120.37 (14) | N4—C19—C18 | 130.86 (15) |
C10—C9—C8 | 120.23 (15) | C14—C19—C18 | 120.03 (15) |
C10—C9—H9 | 119.9 | N6—O2—H2A | 109.5 |
C8—C9—H9 | 119.9 | ||
C6—N1—N2—N3 | 0.52 (15) | C7—C8—C9—C10 | 178.88 (14) |
C7—N1—N2—N3 | 179.96 (12) | C8—C9—C10—C11 | 0.2 (3) |
N1—N2—N3—O1 | −178.89 (12) | C9—C10—C11—C12 | 0.5 (3) |
N1—N2—N3—C1 | 0.15 (16) | C10—C11—C12—C13 | −0.3 (3) |
O1—N3—C1—C6 | 178.25 (13) | C11—C12—C13—C8 | −0.7 (2) |
N2—N3—C1—C6 | −0.73 (16) | C9—C8—C13—C12 | 1.5 (2) |
O1—N3—C1—C2 | −2.6 (3) | C7—C8—C13—C12 | −178.64 (14) |
N2—N3—C1—C2 | 178.37 (15) | C19—N4—N5—N6 | −0.6 (2) |
N3—C1—C2—C3 | −179.72 (15) | N4—N5—N6—C14 | 1.1 (2) |
C6—C1—C2—C3 | −0.8 (2) | N4—N5—N6—O2 | 176.88 (14) |
C1—C2—C3—C4 | −0.1 (2) | N5—N6—C14—C19 | −1.03 (18) |
C2—C3—C4—C5 | 0.9 (3) | O2—N6—C14—C19 | −176.51 (14) |
C3—C4—C5—C6 | −0.7 (2) | N5—N6—C14—C15 | 178.09 (17) |
N2—N1—C6—C1 | −0.96 (15) | O2—N6—C14—C15 | 2.6 (3) |
C7—N1—C6—C1 | 179.66 (13) | N6—C14—C15—C16 | −179.35 (17) |
N2—N1—C6—C5 | −179.96 (15) | C19—C14—C15—C16 | −0.4 (2) |
C7—N1—C6—C5 | 0.7 (3) | C14—C15—C16—C17 | 0.1 (2) |
N3—C1—C6—N1 | 0.98 (15) | C15—C16—C17—C18 | 0.2 (3) |
C2—C1—C6—N1 | −178.23 (13) | C16—C17—C18—C19 | −0.3 (3) |
N3—C1—C6—C5 | −179.87 (13) | N5—N4—C19—C14 | −0.01 (19) |
C2—C1—C6—C5 | 0.9 (2) | N5—N4—C19—C18 | −178.73 (17) |
C4—C5—C6—N1 | 178.71 (15) | N6—C14—C19—N4 | 0.61 (17) |
C4—C5—C6—C1 | −0.2 (2) | C15—C14—C19—N4 | −178.63 (15) |
C6—N1—C7—C8 | 94.88 (17) | N6—C14—C19—C18 | 179.50 (14) |
N1—C7—C8—C9 | −104.04 (16) | C15—C14—C19—C18 | 0.3 (2) |
N1—C7—C8—C13 | 76.11 (17) | C17—C18—C19—N4 | 178.71 (17) |
C13—C8—C9—C10 | −1.3 (2) | C17—C18—C19—C14 | 0.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···N3i | 0.84 | 2.57 | 3.3621 (18) | 157 |
C3—H3···O1ii | 0.95 | 2.50 | 3.200 (2) | 130 |
C7—H7B···Cg1iii | 0.99 | 2.85 | 3.5146 (17) | 125 |
C18—H18···Cg1iv | 0.95 | 2.69 | 3.510 (2) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C6H5N3O·C13H11N3O |
Mr | 360.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 193 |
a, b, c (Å) | 11.2728 (8), 12.2354 (5), 13.1002 (9) |
β (°) | 110.946 (3) |
V (Å3) | 1687.47 (18) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.80 |
Crystal size (mm) | 0.40 × 0.40 × 0.30 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3364, 3197, 2980 |
Rint | 0.102 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.132, 1.08 |
No. of reflections | 3197 |
No. of parameters | 245 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.27 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···N3i | 0.84 | 2.57 | 3.3621 (18) | 157 |
C3—H3···O1ii | 0.95 | 2.50 | 3.200 (2) | 130 |
C7—H7B···Cg1iii | 0.99 | 2.85 | 3.5146 (17) | 125 |
C18—H18···Cg1iv | 0.95 | 2.69 | 3.510 (2) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, y−1/2, −z+1/2. |
References
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761–762. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Ravindran Durai Nayagam, B., Jebas, S. R., Edward Rajkumar, J. P. & Schollmeyer, D. (2009). Acta Cryst. E65, o917. Web of Science CrossRef IUCr Journals Google Scholar
Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wiehl, L. & Schollmeyer, D. (1994). CORINC. University of Mainz, Germany. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As part of our ongoing studies of benzotriazole derivatives (Ravindran et al., 2009; Selvarathy Grace et al., 2012), we now report the crystal structure of the title compound (I), (Fig. 1).
The benzotriazole rings are essentially planar with the maximum deviation from planarity being 0.015 (14) Å for atoms N1 and N5. The mean plane of the benzotriazole ring N1—N3/C1—C6 forms a dihedral angle of 67.56 (7) Å with the mean plane of the phenyl ring (C8—C13).
The crystal packing features weak C—H···π interactions. The hydrogen bonding interactions are shown in Fig 2.