Literature DB >> 21580762

2-(1H-Benzotriazol-1-yl)-1-phenyl-ethanol.

Ozden Ozel Güven, Meral Bayraktar, Simon J Coles, Tuncer Hökelek.

Abstract

In the title compound, C(14)H(13)N(3)O, the benzotriazole ring is oriented at a dihedral angle of 13.43 (4)° with respect to the phenyl ring. In the crystal structure, inter-molecular O-H⋯N hydrogen bonds link the mol-ecules into chains along the b axis. Aromatic π-π contacts between benzene rings and between triazole and benzene rings [centroid-centroid distances = 3.8133 (8) and 3.7810 (8) Å, respectively], as well as a weak C-H⋯π inter-action involving the phenyl ring, are also observed.

Entities: Chemical Disease Species

Year: 2010 PMID： 21580762 PMCID： PMC2983856 DOI： 10.1107/S1600536810011098

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background to the biological activity of benzotriazole derivatives, see: Hirokawa et al. (1998 ▶); Yu et al. (2003 ▶); Kopańska et al. (2004 ▶). For related structures, see: Caira et al. (2004 ▶); Katritzky et al. (2001 ▶); Özel Güven et al. (2008 ▶); Swamy et al. (2006 ▶).

Experimental

Crystal data

C14H13N3O M = 239.27 Orthorhombic, a = 11.0731 (3) Å b = 8.6571 (2) Å c = 25.3436 (7) Å V = 2429.5 (1) Å3 Z = 8 Mo Kα radiation μ = 0.09 mm−1 T = 120 K 0.40 × 0.30 × 0.20 mm

Data collection

Nonius Kappa CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.968, T max = 0.981 11997 measured reflections 2772 independent reflections 2447 reflections with I > 2σ(I) R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.105 S = 1.06 2772 reflections 215 parameters All H-atom parameters refined Δρmax = 0.25 e Å−3 Δρmin = −0.23 e Å−3 Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: 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 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011098/im2186sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011098/im2186Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₃N₃O	F(000) = 1008
M_r = 239.27	D_x = 1.308 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 13033 reflections
a = 11.0731 (3) Å	θ = 2.9–27.5°
b = 8.6571 (2) Å	µ = 0.09 mm⁻¹
c = 25.3436 (7) Å	T = 120 K
V = 2429.5 (1) Å³	Block, colorless
Z = 8	0.40 × 0.30 × 0.20 mm

Nonius Kappa CCD diffractometer	2772 independent reflections
Radiation source: fine-focus sealed tube	2447 reflections with I > 2σ(I)
graphite	R_int = 0.043
φ and ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −14→14
T_min = 0.968, T_max = 0.981	k = −10→11
11997 measured reflections	l = −32→16

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0259P)² + 1.6489P] where P = (F_o² + 2F_c²)/3
2772 reflections	(Δ/σ)_max < 0.001
215 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

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	U_iso*/U_eq
O1	0.02061 (10)	0.04949 (12)	0.40376 (4)	0.0279 (2)
H1	0.090 (2)	0.038 (2)	0.4178 (9)	0.054 (6)*
N1	0.25101 (12)	0.48299 (16)	0.44171 (5)	0.0300 (3)
N2	0.18457 (11)	0.44939 (15)	0.40068 (5)	0.0295 (3)
N3	0.08582 (11)	0.37136 (13)	0.41711 (4)	0.0222 (3)
C1	0.19546 (12)	0.42532 (16)	0.48602 (5)	0.0224 (3)
C2	0.22997 (13)	0.43162 (17)	0.53950 (5)	0.0240 (3)
H2	0.3052 (16)	0.479 (2)	0.5494 (7)	0.029 (4)*
C3	0.15335 (14)	0.36306 (17)	0.57508 (5)	0.0253 (3)
H3	0.1736 (15)	0.3631 (19)	0.6119 (7)	0.030 (4)*
C4	0.04479 (14)	0.29030 (16)	0.55904 (6)	0.0255 (3)
H4	−0.0089 (16)	0.240 (2)	0.5866 (8)	0.036 (5)*
C5	0.01041 (13)	0.28261 (16)	0.50680 (6)	0.0228 (3)
H5	−0.0631 (15)	0.232 (2)	0.4957 (7)	0.028 (4)*
C6	0.08867 (12)	0.35214 (15)	0.47059 (5)	0.0199 (3)
C7	0.00031 (13)	0.31427 (16)	0.37785 (5)	0.0229 (3)
H71	−0.0807 (15)	0.3138 (18)	0.3945 (6)	0.022 (4)*
H72	0.0019 (15)	0.388 (2)	0.3473 (7)	0.028 (4)*
C8	0.03379 (12)	0.15050 (16)	0.36022 (5)	0.0216 (3)
H8	0.1203 (14)	0.1535 (17)	0.3473 (6)	0.021 (4)*
C9	−0.04730 (12)	0.09913 (16)	0.31533 (5)	0.0214 (3)
C10	−0.13758 (13)	−0.00987 (17)	0.32359 (5)	0.0248 (3)
H10	−0.1479 (15)	−0.0567 (19)	0.3588 (7)	0.032 (4)*
C11	−0.21348 (14)	−0.05425 (19)	0.28253 (6)	0.0303 (3)
H11	−0.2784 (17)	−0.134 (2)	0.2882 (7)	0.039 (5)*
C12	−0.19924 (15)	0.00902 (19)	0.23260 (6)	0.0317 (3)
H12	−0.2518 (18)	−0.023 (2)	0.2038 (8)	0.043 (5)*
C13	−0.10914 (15)	0.11692 (19)	0.22396 (6)	0.0318 (3)
H13	−0.0995 (17)	0.162 (2)	0.1892 (8)	0.041 (5)*
C14	−0.03327 (14)	0.16238 (17)	0.26496 (6)	0.0270 (3)
H14	0.0301 (16)	0.238 (2)	0.2584 (7)	0.032 (4)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0291 (6)	0.0264 (5)	0.0282 (5)	−0.0010 (4)	−0.0097 (4)	0.0070 (4)
N1	0.0289 (6)	0.0409 (7)	0.0201 (6)	−0.0107 (5)	0.0015 (5)	−0.0021 (5)
N2	0.0311 (6)	0.0367 (7)	0.0206 (6)	−0.0111 (6)	0.0016 (5)	0.0001 (5)
N3	0.0250 (6)	0.0238 (6)	0.0176 (5)	−0.0032 (5)	−0.0009 (4)	0.0004 (4)
C1	0.0222 (6)	0.0248 (7)	0.0202 (6)	−0.0007 (5)	0.0013 (5)	−0.0008 (5)
C2	0.0235 (7)	0.0265 (7)	0.0221 (7)	0.0007 (6)	−0.0024 (5)	−0.0037 (5)
C3	0.0339 (8)	0.0237 (7)	0.0184 (6)	0.0030 (6)	−0.0022 (6)	−0.0002 (5)
C4	0.0332 (8)	0.0219 (7)	0.0213 (7)	−0.0005 (6)	0.0047 (6)	0.0012 (5)
C5	0.0245 (7)	0.0213 (7)	0.0227 (7)	−0.0025 (5)	0.0015 (5)	−0.0003 (5)
C6	0.0227 (6)	0.0191 (6)	0.0178 (6)	0.0017 (5)	−0.0009 (5)	−0.0002 (5)
C7	0.0269 (7)	0.0240 (7)	0.0178 (6)	0.0001 (5)	−0.0051 (5)	−0.0004 (5)
C8	0.0205 (6)	0.0232 (7)	0.0212 (6)	0.0001 (5)	−0.0013 (5)	−0.0002 (5)
C9	0.0212 (6)	0.0233 (7)	0.0197 (6)	0.0048 (5)	0.0004 (5)	−0.0042 (5)
C10	0.0239 (7)	0.0307 (7)	0.0197 (6)	0.0000 (6)	0.0014 (5)	−0.0046 (6)
C11	0.0269 (7)	0.0376 (8)	0.0263 (7)	−0.0032 (6)	−0.0011 (6)	−0.0098 (6)
C12	0.0322 (8)	0.0401 (9)	0.0227 (7)	0.0071 (7)	−0.0065 (6)	−0.0109 (6)
C13	0.0439 (9)	0.0340 (8)	0.0176 (7)	0.0078 (7)	−0.0013 (6)	−0.0024 (6)
C14	0.0317 (8)	0.0274 (7)	0.0218 (7)	0.0015 (6)	0.0033 (6)	−0.0016 (6)

O1—C8	1.4154 (17)	C7—H71	0.992 (17)
O1—H1	0.86 (2)	C7—H72	1.003 (17)
N1—C1	1.3743 (18)	C8—C7	1.5320 (19)
N2—N1	1.3067 (17)	C8—C9	1.5161 (18)
N3—N2	1.3511 (16)	C8—H8	1.012 (16)
N3—C6	1.3659 (16)	C9—C10	1.390 (2)
N3—C7	1.4597 (17)	C9—C14	1.3978 (19)
C1—C2	1.4091 (18)	C10—C11	1.392 (2)
C2—H2	0.962 (18)	C10—H10	0.986 (18)
C3—C2	1.373 (2)	C11—H11	1.005 (19)
C3—H3	0.960 (17)	C12—C13	1.384 (2)
C4—C3	1.417 (2)	C12—C11	1.388 (2)
C4—C5	1.3793 (19)	C12—H12	0.98 (2)
C4—H4	1.014 (19)	C13—H13	0.97 (2)
C5—H5	0.965 (17)	C14—C13	1.393 (2)
C6—C1	1.3974 (19)	C14—H14	0.972 (18)
C6—C5	1.3983 (19)

C8—O1—H1	107.8 (15)	C8—C7—H71	109.9 (9)
N2—N1—C1	108.51 (12)	C8—C7—H72	111.1 (10)
N1—N2—N3	108.76 (11)	H71—C7—H72	110.3 (13)
N2—N3—C6	110.37 (11)	O1—C8—C7	108.63 (11)
N2—N3—C7	118.95 (11)	O1—C8—C9	110.04 (11)
C6—N3—C7	130.55 (12)	O1—C8—H8	111.5 (9)
N1—C1—C2	130.58 (13)	C9—C8—C7	110.30 (11)
N1—C1—C6	108.35 (12)	C9—C8—H8	108.9 (9)
C6—C1—C2	121.07 (13)	C7—C8—H8	107.4 (9)
C1—C2—H2	120.1 (10)	C10—C9—C8	120.79 (12)
C3—C2—C1	116.58 (13)	C10—C9—C14	118.89 (13)
C3—C2—H2	123.2 (10)	C14—C9—C8	120.31 (13)
C2—C3—C4	121.87 (13)	C9—C10—C11	120.60 (14)
C2—C3—H3	119.6 (10)	C9—C10—H10	119.9 (10)
C4—C3—H3	118.5 (10)	C11—C10—H10	119.5 (10)
C3—C4—H4	119.4 (11)	C10—C11—H11	120.9 (11)
C5—C4—C3	122.08 (13)	C12—C11—C10	120.28 (15)
C5—C4—H4	118.5 (11)	C12—C11—H11	118.8 (10)
C4—C5—C6	115.99 (13)	C11—C12—H12	120.1 (12)
C4—C5—H5	122.4 (10)	C13—C12—C11	119.50 (14)
C6—C5—H5	121.6 (10)	C13—C12—H12	120.4 (12)
N3—C6—C1	104.01 (12)	C12—C13—C14	120.49 (14)
N3—C6—C5	133.57 (13)	C12—C13—H13	119.5 (11)
C1—C6—C5	122.41 (12)	C14—C13—H13	120.0 (12)
N3—C7—C8	110.81 (11)	C9—C14—H14	120.0 (11)
N3—C7—H71	107.3 (9)	C13—C14—C9	120.24 (14)
N3—C7—H72	107.4 (10)	C13—C14—H14	119.8 (11)

N2—N1—C1—C2	−179.62 (15)	C5—C6—C1—N1	−179.32 (13)
N2—N1—C1—C6	0.05 (17)	C5—C6—C1—C2	0.4 (2)
N3—N2—N1—C1	0.35 (17)	N3—C6—C5—C4	−178.54 (14)
C6—N3—N2—N1	−0.64 (16)	C1—C6—C5—C4	0.0 (2)
C7—N3—N2—N1	−177.00 (12)	O1—C8—C7—N3	65.40 (14)
N2—N3—C6—C1	0.64 (15)	C9—C8—C7—N3	−173.92 (11)
N2—N3—C6—C5	179.36 (15)	O1—C8—C9—C10	13.06 (17)
N2—N3—C7—C8	90.35 (15)	O1—C8—C9—C14	−167.73 (12)
C6—N3—C7—C8	−85.16 (17)	C7—C8—C9—C10	−106.78 (15)
C7—N3—C6—C1	176.45 (13)	C7—C8—C9—C14	72.44 (16)
C7—N3—C6—C5	−4.8 (3)	C8—C9—C10—C11	178.62 (13)
N1—C1—C2—C3	179.42 (15)	C14—C9—C10—C11	−0.6 (2)
C6—C1—C2—C3	−0.2 (2)	C8—C9—C14—C13	−178.95 (13)
C4—C3—C2—C1	−0.3 (2)	C10—C9—C14—C13	0.3 (2)
C5—C4—C3—C2	0.7 (2)	C9—C10—C11—C12	0.5 (2)
C3—C4—C5—C6	−0.5 (2)	C13—C12—C11—C10	−0.2 (2)
N3—C6—C1—N1	−0.42 (15)	C11—C12—C13—C14	−0.2 (2)
N3—C6—C1—C2	179.29 (13)	C9—C14—C13—C12	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.85 (2)	1.92 (2)	2.766 (2)	170 (2)
C11—H11···Cg3ⁱⁱ	1.01 (2)	2.94 (2)	3.850 (2)	151 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.85 (2)	1.92 (2)	2.766 (2)	170 (2)
C11—H11⋯Cg3ⁱ	1.01 (2)	2.94 (2)	3.850 (2)	151 (1)

Symmetry code: (i) .

9 in total

1. Regiospecific synthesis of 4-(2-oxoalkyl)pyridines.

Authors: A R Katritzky; S Zhang; T Kurz; M Wang; P J Steel
Journal: Org Lett Date: 2001-09-06 Impact factor: 6.005

2. Microwave-assisted synthesis of N-alkylated benzotriazole derivatives: antimicrobial studies.

Authors: S Nanjunda Swamy; G Sarala; B S Priya; S L Gaonkar; J Shashidhara Prasad; K S Rangappa
Journal: Bioorg Med Chem Lett Date: 2005-11-18 Impact factor: 2.823

3. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

4. Fundamental structure-activity relationships associated with a new structural class of respiratory syncytial virus inhibitor.

Authors: Kuo Long Yu; Yi Zhang; Rita L Civiello; Kathleen F Kadow; Christopher Cianci; Mark Krystal; Nicholas A Meanwell
Journal: Bioorg Med Chem Lett Date: 2003-07-07 Impact factor: 2.823

5. Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of Acanthamoeba castellanii.

Authors: Katarzyna Kopańska; Andzelika Najda; Justyna Zebrowska; Lidia Chomicz; Janusz Piekarczyk; Przemysław Myjak; Maria Bretner
Journal: Bioorg Med Chem Date: 2004-05-15 Impact factor: 3.641

6. A novel series of 6-methoxy-1H-benzotriazole-5-carboxamide derivatives with dual antiemetic and gastroprokinetic activities.

Authors: Y Hirokawa; H Yamazaki; N Yoshida; S Kato
Journal: Bioorg Med Chem Lett Date: 1998-08-04 Impact factor: 2.823

7. Preparation and crystal characterization of a polymorph, a monohydrate, and an ethyl acetate solvate of the antifungal fluconazole.

Authors: Mino R Caira; Khouloud A Alkhamis; Rana M Obaidat
Journal: J Pharm Sci Date: 2004-03 Impact factor: 3.534

8. 1-Phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol.

Authors: Ozden Ozel Güven; Hakan Tahtacı; Simon J Coles; Tuncer Hökelek
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-06-13

9. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20