2-(1H-Benzotriazol-1-yl)-1-(furan-2-yl)ethanol

Özel Güven, Ö.; Bayraktar, M.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536811051798

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o72

doi:10.1107/S1600536811051798

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2-(1H-Benzotriazol-1-yl)-1-(furan-2-yl)ethanol

Özden Özel Güven,^a Meral Bayraktar,^a Simon J. Coles ^b and Tuncer Hökelek ^c ^*

^aDepartment of Chemistry, Zonguldak Karaelmas University, 67100 Zonguldak, Turkey, ^bDepartment of Chemistry, Southampton University, Southampton SO17 1BJ, England, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 30 November 2011; accepted 1 December 2011; online 10 December 2011)

In the title compound, C₁₂H₁₁N₃O₂, the benzotriazole ring system is approximately planar [maximum deviation = 0.008 (1) Å] and its mean plane is oriented at a dihedral angle of 24.05 (4)° with respect to the furan ring. In the crystal, O—H⋯N hydrogen bonds link the molecules into chains along the ac diagonal. π–π stacking between the furan rings, between the triazole and benzene rings, and between the benzene rings [centroid–centroid distances = 3.724 (1), 3.786 (1) and 3.8623 (9) Å] are also observed.

Related literature

For general background to the biological activity of benzotriazole derivatives, see: Hirokawa et al. (1998 ); Yu et al. (2003 ); Kopanska et al. (2004 ). For related structures, see: Caira et al. (2004 ); Katritzky et al. (2001 ); Özel Güven et al. (2008 , 2010 , 2011 ); Nanjunda Swamy et al. (2006 ).

Experimental

Crystal data

C₁₂H₁₁N₃O₂
M_r = 229.24
Monoclinic, P 2₁ /c
a = 11.3606 (4) Å
b = 11.1034 (4) Å
c = 8.7860 (2) Å
β = 96.938 (2)°
V = 1100.16 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 K
0.50 × 0.50 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.953, T_max = 0.981
12372 measured reflections
2531 independent reflections
2166 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.139
S = 1.11
2531 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3ⁱ	0.82	2.26	2.7968 (18)	123
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811051798/xu5402sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051798/xu5402Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051798/xu5402Isup3.cml

checkCIF report

Comment top

Azole compounds have important biological activities. Benzotriazol derivatives also exhibit a good degree of analgesic, anti-inflammatory, diuretic, antiviral and antihypertensive activities (Kopanska et al., 2004; Yu et al., 2003; Hirokawa et al., 1998). Crystal structures of similar compounds like 1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol (Özel Güven et al., 2008), 2-(1H-benzotriazol-1-yl)-1-phenylethanol (Özel Güven et al., 2010), 2-(1H-benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropan-1-ol (Özel Güven et al., 2011), fluconazole (Caira et al., 2004), and other benzotriazole ring possesing compounds (Katritzky et al., 2001; Nanjunda Swamy et al., 2006) have been reported before. Now, we report herein the crystal structure of the title alcohol, (I).

In the molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges. The planar benzotriazole ring [B (N1-N3/C7-C12)] is oriented with respect to the furan [A (O2/C2-C5)] ring at a dihedral angle of A/B = 24.05 (4)°. Atom C6 is 0.043 (2) Å away from the plane of the benzotriazole ring and atoms C1 and O1 are 0.010 (2) and 0.043 (1) Å away from the plane of the furan ring, respectively.

In the crystal, O—H···N hydrogen bonds (table 1) link the molecules into chains (Fig. 2). There also exist π···π contacts between the furan rings, between the triazole and benzene rings and between the benzene rings, Cg1—Cg1ⁱ, Cg2—Cg3ⁱⁱ and Cg3—Cg3ⁱⁱ, may further stabilize the structure [centroid-centroid distances = 3.724 (1), 3.786 (1) and 3.8623 (9) Å; symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) -x, 1 - y, 1 - z; Cg1, Cg2 and Cg3 are the centroids of the rings A (O2/C2-C5), C (N1-N3/C7/C12) and D (C7-C12), respectively].

Related literature top

For general background to the biological activity of benzotriazole derivatives, see: Hirokawa et al. (1998); Yu et al. (2003); Kopanska et al. (2004). For related structures, see: Caira et al. (2004); Katritzky et al. (2001); Özel Güven et al. (2008, 2010, 2011); Nanjunda Swamy et al. (2006).

Experimental top

The title compound, (I), was synthesized by reduction of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanone with sodiumborohydrate. A mixture of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanone (1010 mg, 4.44 mmol) and sodium borohydrate (561 mg, 8.89 mmol) in ethanol (50 ml) was refluxed for 4 h. After evaporation of the solvent, the mixture was neutralized with dilute HCl, and then refluxed for 30 min. After the mixture was cooled, the solution was alkalinized with dilute NaOH and the resulting precipitate was filtered. The filtrate was extracted with chloroform, then the organic phase was dried and evaporated. The residue was crystallized from 2-propanol to obtain colorless crystals suitable for X-ray analysis (yield; 634 mg, 62%).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

2-(1H-Benzotriazol-1-yl)-1-(furan-2-yl)ethanol top

Crystal data top

C₁₂H₁₁N₃O₂	F(000) = 480
M_r = 229.24	D_x = 1.384 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6399 reflections
a = 11.3606 (4) Å	θ = 2.9–27.5°
b = 11.1034 (4) Å	µ = 0.10 mm⁻¹
c = 8.7860 (2) Å	T = 120 K
β = 96.938 (2)°	Block, colorless
V = 1100.16 (6) Å³	0.50 × 0.50 × 0.20 mm
Z = 4

Data collection top

Bruker–Nonius KappaCCD diffractometer	2531 independent reflections
Radiation source: fine-focus sealed tube	2166 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −14→14
T_min = 0.953, T_max = 0.981	k = −14→14
12372 measured reflections	l = −10→11

Refinement top

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)] = 0.054	H-atom parameters constrained
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.0748P)² + 0.4779P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
2531 reflections	Δρ_max = 0.58 e Å⁻³
155 parameters	Δρ_min = −0.55 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: 0.144 (12)

Crystal data top

C₁₂H₁₁N₃O₂	V = 1100.16 (6) Å³
M_r = 229.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.3606 (4) Å	µ = 0.10 mm⁻¹
b = 11.1034 (4) Å	T = 120 K
c = 8.7860 (2) Å	0.50 × 0.50 × 0.20 mm
β = 96.938 (2)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	2531 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2166 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.981	R_int = 0.037
12372 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.11	Δρ_max = 0.58 e Å⁻³
2531 reflections	Δρ_min = −0.55 e Å⁻³
155 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.20677 (10)	0.98199 (10)	0.08354 (12)	0.0223 (3)
H1	0.1559	0.9346	0.1048	0.033*
O2	0.50236 (10)	1.06715 (11)	0.24705 (13)	0.0247 (3)
N1	0.18510 (11)	0.91870 (12)	0.39959 (14)	0.0196 (3)
N2	0.22565 (12)	0.82297 (13)	0.48488 (16)	0.0249 (3)
N3	0.13604 (12)	0.75376 (13)	0.50674 (16)	0.0248 (3)
C1	0.30653 (14)	0.97510 (14)	0.19621 (17)	0.0193 (3)
H1A	0.3392	0.8933	0.1989	0.023*
C2	0.39723 (13)	1.06237 (14)	0.15318 (17)	0.0194 (3)
C3	0.57056 (15)	1.15175 (15)	0.18424 (19)	0.0257 (4)
H3	0.6471	1.1732	0.2247	0.031*
C4	0.51146 (15)	1.19920 (15)	0.05628 (19)	0.0252 (4)
H4	0.5385	1.2581	−0.0062	0.030*
C5	0.39773 (14)	1.14020 (15)	0.03582 (18)	0.0238 (4)
H5	0.3367	1.1533	−0.0429	0.029*
C6	0.26911 (14)	1.00691 (14)	0.35398 (17)	0.0214 (3)
H6A	0.3386	1.0091	0.4298	0.026*
H6B	0.2330	1.0862	0.3496	0.026*
C7	0.06500 (13)	0.91156 (13)	0.36343 (16)	0.0178 (3)
C8	−0.01985 (14)	0.98551 (14)	0.27982 (17)	0.0202 (3)
H8	0.0010	1.0560	0.2326	0.024*
C9	−0.13571 (14)	0.94734 (15)	0.27193 (17)	0.0226 (4)
H9	−0.1949	0.9939	0.2182	0.027*
C10	−0.16792 (14)	0.83958 (15)	0.34283 (17)	0.0232 (4)
H10	−0.2474	0.8174	0.3339	0.028*
C11	−0.08469 (14)	0.76679 (14)	0.42472 (18)	0.0222 (4)
H11	−0.1059	0.6962	0.4713	0.027*
C12	0.03398 (13)	0.80499 (13)	0.43403 (17)	0.0191 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0207 (6)	0.0231 (6)	0.0226 (6)	−0.0047 (4)	0.0004 (4)	−0.0002 (4)
O2	0.0204 (6)	0.0259 (6)	0.0271 (6)	−0.0032 (4)	−0.0001 (4)	0.0002 (4)
N1	0.0181 (6)	0.0205 (6)	0.0205 (6)	0.0001 (5)	0.0030 (5)	0.0020 (5)
N2	0.0224 (7)	0.0249 (7)	0.0272 (7)	0.0045 (5)	0.0023 (5)	0.0044 (5)
N3	0.0231 (7)	0.0221 (7)	0.0293 (7)	0.0043 (5)	0.0038 (5)	0.0059 (6)
C1	0.0204 (7)	0.0172 (7)	0.0203 (7)	−0.0007 (6)	0.0028 (6)	−0.0012 (5)
C2	0.0168 (7)	0.0204 (7)	0.0213 (7)	0.0006 (6)	0.0031 (6)	−0.0038 (6)
C3	0.0203 (8)	0.0251 (8)	0.0322 (8)	−0.0052 (6)	0.0054 (6)	−0.0052 (6)
C4	0.0246 (8)	0.0237 (8)	0.0285 (8)	−0.0047 (6)	0.0087 (6)	−0.0016 (6)
C5	0.0223 (8)	0.0264 (8)	0.0228 (7)	−0.0012 (6)	0.0029 (6)	0.0007 (6)
C6	0.0201 (7)	0.0221 (8)	0.0223 (7)	−0.0039 (6)	0.0041 (6)	−0.0025 (6)
C7	0.0185 (7)	0.0178 (7)	0.0173 (7)	−0.0002 (6)	0.0034 (5)	−0.0017 (5)
C8	0.0248 (8)	0.0178 (7)	0.0184 (7)	0.0020 (6)	0.0040 (6)	0.0030 (5)
C9	0.0213 (8)	0.0274 (8)	0.0185 (7)	0.0056 (6)	0.0002 (6)	−0.0009 (6)
C10	0.0190 (7)	0.0286 (8)	0.0224 (7)	−0.0031 (6)	0.0043 (6)	−0.0042 (6)
C11	0.0243 (8)	0.0191 (8)	0.0244 (8)	−0.0022 (6)	0.0074 (6)	−0.0004 (6)
C12	0.0212 (8)	0.0169 (7)	0.0195 (7)	0.0022 (6)	0.0041 (6)	0.0004 (5)

Geometric parameters (Å, º) top

O1—C1	1.4139 (18)	C4—H4	0.9300
O1—H1	0.8200	C5—C4	1.440 (2)
O2—C2	1.3681 (19)	C5—H5	0.9300
O2—C3	1.375 (2)	C6—H6A	0.9700
N1—N2	1.3492 (18)	C6—H6B	0.9700
N1—C6	1.4571 (19)	C7—C12	1.401 (2)
N1—C7	1.365 (2)	C8—C7	1.404 (2)
N3—N2	1.308 (2)	C8—C9	1.376 (2)
N3—C12	1.377 (2)	C8—H8	0.9300
C1—C6	1.539 (2)	C9—H9	0.9300
C1—H1A	0.9800	C10—C9	1.417 (2)
C2—C1	1.496 (2)	C10—H10	0.9300
C2—C5	1.346 (2)	C11—C10	1.379 (2)
C3—C4	1.345 (2)	C11—C12	1.406 (2)
C3—H3	0.9300	C11—H11	0.9300

C1—O1—H1	109.5	N1—C6—C1	110.77 (12)
C2—O2—C3	106.13 (12)	N1—C6—H6A	109.5
N2—N1—C7	110.36 (12)	N1—C6—H6B	109.5
N2—N1—C6	119.43 (12)	C1—C6—H6A	109.5
C7—N1—C6	130.13 (13)	C1—C6—H6B	109.5
N3—N2—N1	108.96 (13)	H6A—C6—H6B	108.1
N2—N3—C12	108.40 (13)	N1—C7—C8	133.73 (14)
O1—C1—C2	107.84 (12)	N1—C7—C12	104.11 (13)
O1—C1—C6	109.45 (12)	C12—C7—C8	122.15 (14)
O1—C1—H1A	109.6	C7—C8—H8	122.0
C2—C1—C6	110.64 (12)	C9—C8—C7	115.98 (14)
C2—C1—H1A	109.6	C9—C8—H8	122.0
C6—C1—H1A	109.6	C8—C9—C10	122.27 (15)
O2—C2—C1	116.78 (13)	C8—C9—H9	118.9
C5—C2—O2	110.66 (14)	C10—C9—H9	118.9
C5—C2—C1	132.56 (14)	C9—C10—H10	119.1
O2—C3—H3	124.6	C11—C10—C9	121.81 (15)
C4—C3—O2	110.75 (14)	C11—C10—H10	119.1
C4—C3—H3	124.6	C10—C11—C12	116.47 (14)
C3—C4—C5	106.01 (14)	C10—C11—H11	121.8
C3—C4—H4	127.0	C12—C11—H11	121.8
C5—C4—H4	127.0	N3—C12—C7	108.16 (13)
C2—C5—C4	106.45 (14)	N3—C12—C11	130.53 (15)
C2—C5—H5	126.8	C7—C12—C11	121.31 (14)
C4—C5—H5	126.8

C6—N1—N2—N3	−177.41 (13)	C5—C2—C1—O1	0.9 (2)
C7—N1—N2—N3	−0.44 (17)	C5—C2—C1—C6	−118.73 (19)
N2—N1—C6—C1	92.27 (16)	O2—C2—C5—C4	−0.09 (18)
C7—N1—C6—C1	−84.02 (19)	C1—C2—C5—C4	−179.58 (15)
N2—N1—C7—C8	179.68 (16)	O2—C3—C4—C5	−0.27 (18)
N2—N1—C7—C12	0.62 (16)	C2—C5—C4—C3	0.21 (18)
C6—N1—C7—C8	−3.8 (3)	N1—C7—C12—N3	−0.58 (16)
C6—N1—C7—C12	177.17 (14)	N1—C7—C12—C11	179.06 (14)
C12—N3—N2—N1	0.05 (17)	C8—C7—C12—N3	−179.77 (13)
N2—N3—C12—C7	0.34 (17)	C8—C7—C12—C11	−0.1 (2)
N2—N3—C12—C11	−179.25 (15)	C9—C8—C7—N1	−178.60 (15)
C3—O2—C2—C1	179.51 (13)	C9—C8—C7—C12	0.3 (2)
C3—O2—C2—C5	−0.07 (17)	C7—C8—C9—C10	−0.4 (2)
C2—O2—C3—C4	0.22 (18)	C11—C10—C9—C8	0.3 (2)
O1—C1—C6—N1	64.08 (16)	C10—C11—C12—N3	179.57 (15)
C2—C1—C6—N1	−177.23 (12)	C10—C11—C12—C7	0.0 (2)
O2—C2—C1—O1	−178.53 (12)	C12—C11—C10—C9	−0.1 (2)
O2—C2—C1—C6	61.80 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3ⁱ	0.82	2.26	2.7968 (18)	123

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁N₃O₂
M_r	229.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	11.3606 (4), 11.1034 (4), 8.7860 (2)
β (°)	96.938 (2)
V (Å³)	1100.16 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.50 × 0.20

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.953, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	12372, 2531, 2166
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.139, 1.11
No. of reflections	2531
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.55

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3ⁱ	0.82	2.26	2.7968 (18)	123

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The authors acknowledge the Zonguldak Karaelmas University Research Fund (project No. 2010-13-02-05).

References

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