2-(1H-Benzotriazol-1-yl)-3-(2,6-dichloro-phen-yl)-1-phenyl-propan-1-ol.

Abstract

The asymmetric unit of the title compound, C(21)H(17)Cl(2)N(3)O, contains two crystallographically independent mol-ecules with similar conformations. The benzotriazole ring is oriented at dihedral angles of 30.61 (5) and 43.36 (5)°, respectively, to the phenyl and dichloro-phenyl rings in one mol-ecule, and 32.25 (5) and 41.04 (5)° in the other. The dihedral angles between the phenyl and dichloro-phenyl rings are 66.38 (7) and 66.14 (6)° in the two mol-ecules. An intra-molecular O-H⋯N hydrogen bond links the benzotriazole ring and phenyl-propanol unit in each mol-ecule. In the crystal, weak inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into chains along the a axis. π-π stacking between the dichloro-phenyl rings [centroid-centroid distances = 3.809 (1) and 3.735 (1) Å] may further stabilize the crystal structure.

Full text

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2-(1H-Benzotriazol-1-yl)-3-(2,6-dichloro-
phenyl)-1-phenylpropan-1-ol
O ¨zden O ¨zel Gu ¨ven,aSeval C ¸apanlar,aSimon J. Colesband
Tuncer Ho ¨kelekc*
aDepartment of Chemistry, Zonguldak Karaelmas University, 67100 Zonguldak,
Turkey,bDepartment of Chemistry, Southampton University, SO17 1BJ
Southampton, England, andcDepartment of Physics, Hacettepe University, 06800
Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr
Received 12 August 2011; accepted 24 August 2011
Key indicators: single-crystal X-ray study; T = 120 K; mean ?(C–C) = 0.003 A ˚;
R factor = 0.042; wR factor = 0.108; data-to-parameter ratio = 17.9.
The asymmetric unit of the title compound, C21H17Cl2N3O,
contains two crystallographically independent molecules with
similar conformations. The benzotriazole ring is oriented at
dihedral angles of 30.61 (5) and 43.36 (5)?, respectively, to the
phenyl and dichlorophenyl rings in one molecule, and
32.25 (5) and 41.04 (5)?in the other. The dihedral angles
between the phenyl and dichlorophenyl rings are 66.38 (7) and
66.14 (6)?in the two molecules. An intramolecular O—H???N
hydrogen bond links the benzotriazole ring and phenyl-
propanol unit in each molecule. In the crystal, weak
intermolecular C—H???N hydrogen bonds link the molecules
into chains along the a axis. ?–? stacking between the
dichlorophenyl rings [centroid–centroid distances = 3.809 (1)
and 3.735 (1) A˚] may further stabilize the crystal structure.
Related literature
For the biological activity of azole compounds, see: Cozzi et al.
(1994) and of triazole derivatives, see: Jin et al. (2006). For
related structures, see: O¨zel Gu ¨ven et al. (2007, 2008, 2010).
Experimental
Crystal data
C21H17Cl2N3O
Mr= 398.28
Triclinic, P1
a = 9.3894 (2) A˚
b = 9.4947 (2) A˚
c = 21.2687 (3) A˚
? = 91.415 (2)?
? = 92.324 (2)?
? = 90.406 (1)?
V = 1893.90 (6) A˚3
Z = 4
Mo K? radiation
? = 0.36 mm?1
T = 120 K
0.4 ? 0.4 ? 0.3 mm
Data collection
Nonius KappaCCD diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
Tmin= 0.866, Tmax= 0.897
40396 measured reflections
8697 independent reflections
7206 reflections with I > 2?(I)
Rint= 0.044
Refinement
R[F2> 2?(F2)] = 0.042
wR(F2) = 0.108
S = 1.07
8697 reflections
487 parameters
H-atom parameters constrained
??max= 0.43 e A˚?3
??min= ?0.73 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
O1—H1A???N2
O10—H1B???N20
C19—H19???N3i
C190—H190???N30ii
Symmetry codes: (i) x þ 1;y;z; (ii) x;y þ 1;z.
D—HH???AD???AD—H???A
0.82
0.82
0.93
0.93
2.56
2.52
2.54
2.53
3.1254 (19)
3.0881 (19)
3.420 (2)
3.410 (2)
127
128
158
159
Data collection: COLLECT (Nonius, 1998); cell refinement:
DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduc-
tion: DENZO and COLLECT; program(s) used to solve structure:
SHELXS97 (Sheldrick, 2008); program(s) used to refine structure:
SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for
Windows (Farrugia, 1997); software used to prepare material for
publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
The authors acknowledge Zonguldak Karaelmas University
Research Fund (project No: 2010-13-02-06).
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: XU5297).
References
Cozzi, P., Giordani, A., Menichincheri, M., Pillan, A., Pinciroli, V., Rossi, A.,
Tonani, R., Volpi, D., Tamburin, M., Ferrario, R., Fusar, D. & Salvati, P.
(1994). J. Med. Chem. 37, 3588–3604.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Jin, Z., Hu, Y., Huo, A., Tao, W., Shao, L., Liu, J. & Fang, J. (2006). J.
Organomet. Chem. 691, 2340–2345.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M.
Sweet, pp. 307–326. New York: Academic Press.
O¨zel Gu ¨ven, O¨., Bayraktar, M., Coles, S. J. & Ho ¨kelek, T. (2010). Acta Cryst.
E66, o959.
O¨zelGu ¨ven, O¨.,Erdog ˘an,T.,C ¸aylak,N. &Ho ¨kelek,T.(2007). ActaCryst.E63,
o3638.
O¨zel Gu ¨ven, O¨., Tahtacı, H., Coles, S. J. & Ho ¨kelek, T. (2008). Acta Cryst. E64,
o1254.
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin,
USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
organic compounds
o2510
O ¨zel Gu ¨ven et al.
doi:10.1107/S1600536811034738
Acta Cryst. (2011). E67, o2510
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials

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supplementary materials
sup-1
Acta Cryst. (2011). E67, o2510 [ doi:10.1107/S1600536811034738 ]
2-(1H-Benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropan-1-ol
Ö. Özel Güven, S. Çapanlar, S. J. Coles and T. Hökelek
Comment
Azole compounds have important biological activities. In literature 2-(1H-imidazol-1-yl)-1,3-diphenylpropan-1-one and its
derivatives have been reported that they show both high and selective thromboxane A2 receptor antagonist and thromboxane
A2 synthase inhibitory activity (Cozzi et al., 1994). Some 1H-1,2,4-triazole derivatives have been known as antifungal and
plant growth regulatory agents (Jin et al., 2006). Crystal structures of similar compounds like ketone having benzimidazole
and furan rings (Özel Güven et al., 2007) and alcohols having 1,2,4-triazole and benzotriazole rings have been reported
(Özel Güven et al., 2008; Özel Güven et al., 2010). Now, we report herein the crystal structure of the title benzotriazole
derivative, (I).
The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules, in which
they differ slightly in the orientations of the 2-6-dichlorophenyl units and the bond lengths and angles are generally within
normal ranges. The intramolecular O—H···N hydrogen bonds (Table 1) link the benzotriazole rings and phenylpropan units.
In each molecule, the planar benzotriazole rings [A (N1-N3/C9-C14) and A' (N1'-N3'/C9'-C14')] are oriented with respect
to the phenyl [B (C3-C8) and B' (C3'-C8')] and 2-6-dichlorophenyl [C (C16-C21)] and C' (C16'-C21')] rings at dihedral
angles of A/B = 30.61 (5), A/C = 43.36 (5) ° and A'/B' = 32.25 (5), A'/C' = 41.04 (5) °. The dihedral angles between phenyl
rings are B/C = 66.38 (7) and B'/C' = 66.14 (6) °. Atoms C1 and C1' are -0.044 (2) and 0.086 (2) Å away from the planes
of the benzotriazole rings, respectively.
In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 1) link the molecules into chains along the a-axis
(Fig. 2). The π–π contacts between the 2-6-dichlorophenyl rings, Cg3—Cg3i and Cg3'—Cg3'ii, [symmetry codes: (i) 2 - x, 2
- y, - z, (ii) 1 - x, 1 - y, 1 - z, where Cg3 and Cg3' are the centroids of the rings C (C16-C21)] and C' (C16'-C21'), respectively],
may further stabilize the structure, with centroid-centroid distances of 3.809 (1) and 3.735 (1) Å, respectively.
Experimental
The title compound, (I), was synthesized by the reduction of 2-(1H-benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenyl-
propane-1-one. Sodiumborohydride (38.21 mg, 1.01 mmol) was added to a solution of 2-(1H-benzotriazol-1-yl)-3-(2,6-di-
chlorophenyl)-1-phenylpropane-1-one (200 mg, 0.505 mmol) in ethanol (15 ml). The mixture was refluxed for 5 h. The
solvent was removed and the mixture was neutralized with dilute HCl, and then refluxed for 30 min. After cooling the
mixture, it was alkalinized with dilute NaOH. The precipitate was filtered and washed with ethanol. The filtrate was extrac-
ted with chloroform, then the organic phase was dried and solvents were removed by rotary evaporator. The residue was
purified with column chromatography using hexane: ethyl acetate (7:3) mixture as solvent. The product was crystallized
from benzene to obtain colorless single crystals suitable for X-ray analysis (yield; 82 mg, 41%).

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supplementary materials
sup-2
Refinement
H atoms were positioned geometrically with O—H = 0.82 for hydroxy H, and C—H = 0.93, 0.97 and 0.98 Å for aromatic,
methylene and methine H-atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = k × Ueq(C,O),
where k = 1.5 for hydroxy H-atoms and k = 1.2 for all other H-atoms.
Figures
Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Dis-
placement ellipsoids are drawn at the 50% probability level. H-atoms have been omitted for
clarity.
Fig. 2. A view of the crystal packing of the title compound. The intermolecular C—H···N hy-
drogen bonds are shown as dashed lines [H-atoms not involved in hydrogen bonding have
been omitted for clarity].
2-(1H-Benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropan-1-ol
Crystal data
C21H17Cl2N3O
Mr = 398.28
Z = 4
F(000) = 824
Dx = 1.397 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 14651 reflections
θ = 2.9–27.5°
µ = 0.36 mm−1
T = 120 K
Block, colorless
0.4 × 0.4 × 0.3 mm
Triclinic, P1
Hall symbol: -P 1
a = 9.3894 (2) Å
b = 9.4947 (2) Å
c = 21.2687 (3) Å
α = 91.415 (2)°
β = 92.324 (2)°
γ = 90.406 (1)°
V = 1893.90 (6) Å3
Data collection
Nonius KappaCCD
diffractometer
Radiation source: fine-focus sealed tube
graphite
φ and ω scans
Absorption correction: multi-scan
8697 independent reflections
7206 reflections with I > 2σ(I)
Rint = 0.044
θmax = 27.6°, θmin = 3.0°
h = −12→12

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supplementary materials
sup-3
(SADABS; Sheldrick, 2007)
Tmin = 0.866, Tmax = 0.897
40396 measured reflections
k = −12→11
l = −27→27
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.042
wR(F2) = 0.108
H-atom parameters constrained
S = 1.07
w = 1/[σ2(Fo2) + (0.0504P)2 + 0.9534P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.43 e Å−3
Δρmin = −0.73 e Å−3
8697 reflections
487 parameters
0 restraints
Special details
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, convention-
al 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 calculat-
ing 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)
x
0.77473 (4)
0.97499 (5)
0.42613 (13)
0.4009
0.60715 (15)
0.50172 (15)
0.49164 (16)
0.64956 (17)
0.7061
0.52030 (18)
0.4698
0.57040 (18)
0.5683 (2)
0.5318
0.6205 (3)
y
1.06219 (5)
0.66618 (5)
0.61760 (13)
0.6380
0.74669 (14)
0.83379 (15)
0.82583 (16)
0.73778 (17)
0.6522
0.72524 (18)
0.8152
0.69279 (18)
0.7957 (2)
0.8842
0.7673 (2)
z
0.104106 (19)
−0.05798 (2)
−0.02537 (6)
0.0101
0.06575 (6)
0.08432 (7)
0.14548 (7)
0.00021 (7)
−0.0048
−0.04605 (8)
−0.0462
−0.11180 (8)
−0.15719 (9)
−0.1479
−0.21634 (10)
Uiso*/Ueq
0.02207 (10)
0.03245 (12)
0.0256 (3)
0.038*
0.0162 (3)
0.0200 (3)
0.0206 (3)
0.0149 (3)
0.018*
0.0193 (3)
0.023*
0.0197 (4)
0.0284 (4)
0.034*
0.0366 (5)
Cl1
Cl2
O1
H1A
N1
N2
N3
C1
H1
C2
H2
C3
C4
H4
C5