5-(5′-Fluoro-2′-meth­oxy­biphenyl-3-yl)-1,3,4-oxa­diazol-2-amine

Usha, M.K.; Ramaprasad, G.C.; Kalluraya, B.; Kant, R.; Gupta, V.K.; Revannasiddaiah, D.

doi:10.1107/S1600536813031206

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1788

doi:10.1107/S1600536813031206

Open

access

5-(5′-Fluoro-2′-methoxybiphenyl-3-yl)-1,3,4-oxadiazol-2-amine

M. K. Usha,^a G. C. Ramaprasad,^b Balakrishna Kalluraya,^b Rajni Kant,^c Vivek K. Gupta ^c and D. Revannasiddaiah ^a ^*

^aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^cPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
^*Correspondence e-mail: dr@physics.uni-mysore.ac.in

(Received 24 October 2013; accepted 13 November 2013; online 20 November 2013)

In the title compound, C₁₅H₁₂FN₃O₂, the dihedral angles between the central benzene ring and the pendant benzene and oxadiazole rings are 45.05 (13) and 15.60 (14)°, respectively. The C atom of the methoxy group is roughly coplanar with its attached ring [displacement = 0.178 (4) Å]. In the crystal, N—H⋯N hydrogen bonds link the molecules into [010] chains. Weak C—H⋯π interactions are also observed.

CCDC reference: 962871

Related literature

For background to the title compound, see: Ainsworth (1965 ); Paik et al. (2002 ); Kulkarni et al. (2004 ). For a related structure, see: Zheng et al. (2012 ).

Experimental

Crystal data

C₁₅H₁₂FN₃O₂
M_r = 285.28
Monoclinic, P 2₁ /c
a = 12.9105 (9) Å
b = 6.1738 (4) Å
c = 16.9255 (11) Å
β = 90.341 (7)°
V = 1349.05 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.806, T_max = 1.000
5027 measured reflections
2650 independent reflections
1382 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.135
S = 1.01
2650 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯N3ⁱ	0.86	2.13	2.972 (3)	166
N6—H6B⋯N4ⁱⁱ	0.86	2.29	3.118 (3)	161
C17—H17⋯Cg3ⁱⁱⁱ	0.93	2.72	3.53	146
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 962871

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813031206/hb7155sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031206/hb7155Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031206/hb7155Isup3.cml

checkCIF report

Comment top

The title compound, C₁₅H₁₂FN₃O₂, a derivative of 1,3,4 oxadiazole (Ainsworth, 1965), has a wide variety of uses, particularly as a bioactive compound in medicine and agriculture, as a dye stuff, and used in UV absorbing and fluorescent materials, heat resistant polymers and scintillators (Paik et al., 2002; Kulkarni et al., 2004). As part of our studies in this area, we now report the structure of the title compound.

The bond distances in the title compound are comparable to the closely related structure 5-(4-Methylphenyl)-1,3,4-oxadiazol-2-amine (Zheng et al., 2012). The oxadiazole ring A makes dihedral angles of 15.64 (9)° and 55.84 (1)° respectively, with the phenyl rings B and C. The dihedral angle between the phenyl ring B and ring C is 45.19 (1)°. Classical N6—H6A···N3 and N6—H6B···N4 hydrogen bonds link the adjacent molecules into [010] chains. Weak C—H···π interactions are also observed.

Related literature top

For background to the title compound, see: Ainsworth (1965); Paik et al. (2002); Kulkarni et al. (2004). For a related structure, see: Zheng et al. (2012).

Experimental top

To a solution of 5'-fluoro-2'-methoxybiphenyl-3-carbohydrazide (3.84 mmol)in 1,4-dioxane (10 ml) cyanogen bromide (3.84 mmol) was added, followed by a solution of sodium bicarbonate (3.84 mmol) in water (10 ml). The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was taken in ethyl acetate (100 ml), washed with water (20 ml) followed by saturated sodium chloride solution (20 ml) and dried over sodium sulfate. The resulting solution was concentrated and purified by column chromatography [30–40% ethyl acetate in petroleum ether] to afford the title compound (M.P. 223–226°C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the molecule with displacement ellipsoids drawn at the 40% probability level.
	Fig. 2. The packing arrangement of molecules viewed along the a axis.

5-(5'-Fluoro-2'-methoxybiphenyl-3-yl)-1,3,4-oxadiazol-2-amine top

Crystal data top

C₁₅H₁₂FN₃O₂	F(000) = 592
M_r = 285.28	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1316 reflections
a = 12.9105 (9) Å	θ = 4.1–28.0°
b = 6.1738 (4) Å	µ = 0.11 mm⁻¹
c = 16.9255 (11) Å	T = 293 K
β = 90.341 (7)°	Block, colourless
V = 1349.05 (16) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer	2650 independent reflections
Radiation source: fine-focus sealed tube	1382 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scans	h = −8→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −7→4
T_min = 0.806, T_max = 1.000	l = −17→20
5027 measured reflections

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0316P)²] where P = (F_o² + 2F_c²)/3
2650 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₂FN₃O₂	V = 1349.05 (16) Å³
M_r = 285.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9105 (9) Å	µ = 0.11 mm⁻¹
b = 6.1738 (4) Å	T = 293 K
c = 16.9255 (11) Å	0.30 × 0.20 × 0.20 mm
β = 90.341 (7)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer	2650 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	1382 reflections with I > 2σ(I)
T_min = 0.806, T_max = 1.000	R_int = 0.048
5027 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
2650 reflections	Δρ_min = −0.18 e Å⁻³
191 parameters

Special details top

Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01–02-2013 CrysAlis171. NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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) top

	x	y	z	U_iso*/U_eq
O1	0.89022 (14)	0.0443 (3)	0.56943 (11)	0.0411 (5)
C2	0.9336 (2)	0.0508 (4)	0.64301 (15)	0.0357 (7)
N3	0.95451 (18)	−0.1405 (3)	0.67077 (13)	0.0435 (6)
N4	0.92173 (18)	−0.2865 (3)	0.61121 (14)	0.0440 (6)
C5	0.8848 (2)	−0.1745 (4)	0.55387 (16)	0.0361 (7)
N6	0.94739 (18)	0.2434 (3)	0.67575 (14)	0.0522 (7)
H6A	0.9738	0.2534	0.7224	0.063*
H6B	0.9299	0.3586	0.6504	0.063*
C7	0.8429 (2)	−0.2443 (4)	0.47839 (16)	0.0394 (7)
C8	0.8602 (2)	−0.4578 (4)	0.45329 (17)	0.0454 (8)
H8	0.8959	−0.5549	0.4854	0.054*
C9	0.8235 (2)	−0.5213 (4)	0.38043 (18)	0.0480 (8)
H9	0.8363	−0.6615	0.3628	0.058*
C10	0.7682 (2)	−0.3804 (4)	0.33300 (17)	0.0466 (8)
H10	0.7439	−0.4268	0.2840	0.056*
C11	0.7485 (2)	−0.1694 (4)	0.35787 (16)	0.0388 (7)
C12	0.7856 (2)	−0.1043 (4)	0.43139 (16)	0.0405 (7)
H12	0.7718	0.0352	0.4493	0.049*
C13	0.6929 (2)	−0.0182 (4)	0.30377 (17)	0.0411 (7)
C14	0.7207 (2)	−0.0126 (5)	0.22425 (18)	0.0506 (8)
H14	0.7731	−0.1027	0.2059	0.061*
C15	0.6709 (2)	0.1257 (5)	0.17307 (18)	0.0524 (9)
F15	0.70017 (16)	0.1262 (3)	0.09598 (11)	0.0846 (7)
C16	0.5951 (3)	0.2629 (5)	0.19672 (19)	0.0531 (9)
H16	0.5637	0.3574	0.1611	0.064*
C17	0.5654 (2)	0.2585 (5)	0.27592 (17)	0.0517 (9)
H17	0.5122	0.3480	0.2932	0.062*
C18	0.6147 (2)	0.1221 (4)	0.32879 (17)	0.0441 (8)
O19	0.58667 (17)	0.1049 (3)	0.40644 (12)	0.0614 (7)
C20	0.5209 (3)	0.2668 (6)	0.4382 (2)	0.0936 (14)
H20A	0.5506	0.4071	0.4290	0.140*
H20B	0.5134	0.2441	0.4940	0.140*
H20C	0.4541	0.2588	0.4130	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0593 (13)	0.0289 (9)	0.0351 (11)	0.0003 (9)	−0.0166 (10)	0.0016 (9)
C2	0.0461 (17)	0.0308 (14)	0.0301 (16)	0.0027 (12)	−0.0122 (14)	0.0017 (13)
N3	0.0615 (17)	0.0327 (12)	0.0360 (15)	0.0038 (11)	−0.0156 (13)	0.0011 (12)
N4	0.0553 (16)	0.0352 (13)	0.0412 (15)	0.0026 (11)	−0.0122 (14)	0.0020 (11)
C5	0.0457 (17)	0.0279 (14)	0.0345 (17)	−0.0006 (12)	−0.0035 (14)	−0.0008 (13)
N6	0.0814 (19)	0.0304 (12)	0.0444 (16)	0.0014 (12)	−0.0292 (15)	−0.0041 (12)
C7	0.0481 (17)	0.0339 (15)	0.0362 (18)	−0.0033 (13)	−0.0061 (15)	0.0014 (14)
C8	0.0564 (19)	0.0326 (14)	0.0471 (19)	−0.0002 (14)	−0.0083 (16)	0.0077 (14)
C9	0.061 (2)	0.0363 (15)	0.047 (2)	−0.0004 (14)	−0.0050 (17)	−0.0040 (15)
C10	0.060 (2)	0.0403 (17)	0.0391 (18)	−0.0048 (14)	−0.0127 (16)	−0.0072 (14)
C11	0.0448 (18)	0.0384 (15)	0.0331 (17)	−0.0026 (13)	−0.0104 (15)	−0.0035 (13)
C12	0.0461 (17)	0.0359 (15)	0.0393 (18)	−0.0002 (13)	−0.0103 (15)	−0.0027 (14)
C13	0.0440 (18)	0.0432 (17)	0.0359 (18)	−0.0017 (13)	−0.0122 (15)	−0.0060 (14)
C14	0.0465 (19)	0.058 (2)	0.047 (2)	0.0030 (15)	−0.0033 (16)	0.0008 (17)
C15	0.053 (2)	0.066 (2)	0.0376 (19)	−0.0013 (17)	−0.0043 (17)	0.0113 (17)
F15	0.0898 (16)	0.1211 (17)	0.0430 (12)	0.0135 (13)	0.0050 (12)	0.0220 (12)
C16	0.063 (2)	0.052 (2)	0.044 (2)	−0.0017 (17)	−0.0132 (18)	0.0107 (17)
C17	0.056 (2)	0.0550 (19)	0.044 (2)	0.0098 (16)	−0.0097 (17)	0.0001 (17)
C18	0.0494 (19)	0.0460 (17)	0.0367 (18)	−0.0024 (14)	−0.0126 (16)	0.0019 (15)
O19	0.0755 (17)	0.0654 (15)	0.0433 (14)	0.0219 (12)	−0.0017 (13)	−0.0034 (12)
C20	0.131 (4)	0.092 (3)	0.059 (3)	0.044 (3)	0.005 (3)	−0.012 (2)

Geometric parameters (Å, º) top

O1—C2	1.363 (3)	C11—C13	1.490 (4)
O1—C5	1.378 (3)	C12—H12	0.9300
C2—N3	1.299 (3)	C13—C14	1.396 (4)
C2—N6	1.323 (3)	C13—C18	1.398 (4)
N3—N4	1.415 (3)	C14—C15	1.374 (4)
N4—C5	1.281 (3)	C14—H14	0.9300
C5—C7	1.450 (3)	C15—C16	1.356 (4)
N6—H6A	0.8600	C15—F15	1.361 (3)
N6—H6B	0.8600	C16—C17	1.397 (4)
C7—C12	1.386 (3)	C16—H16	0.9300
C7—C8	1.403 (3)	C17—C18	1.381 (4)
C8—C9	1.375 (4)	C17—H17	0.9300
C8—H8	0.9300	C18—O19	1.369 (3)
C9—C10	1.380 (4)	O19—C20	1.420 (3)
C9—H9	0.9300	C20—H20A	0.9600
C10—C11	1.393 (3)	C20—H20B	0.9600
C10—H10	0.9300	C20—H20C	0.9600
C11—C12	1.390 (3)

C2—O1—C5	102.9 (2)	C7—C12—H12	119.6
N3—C2—N6	129.7 (3)	C11—C12—H12	119.6
N3—C2—O1	112.8 (2)	C14—C13—C18	117.9 (3)
N6—C2—O1	117.5 (2)	C14—C13—C11	118.8 (3)
C2—N3—N4	105.1 (2)	C18—C13—C11	123.3 (3)
C5—N4—N3	107.7 (2)	C15—C14—C13	120.1 (3)
N4—C5—O1	111.5 (2)	C15—C14—H14	120.0
N4—C5—C7	130.0 (2)	C13—C14—H14	120.0
O1—C5—C7	118.6 (2)	C16—C15—F15	119.1 (3)
C2—N6—H6A	120.0	C16—C15—C14	122.6 (3)
C2—N6—H6B	120.0	F15—C15—C14	118.3 (3)
H6A—N6—H6B	120.0	C15—C16—C17	118.3 (3)
C12—C7—C8	119.9 (3)	C15—C16—H16	120.9
C12—C7—C5	121.0 (2)	C17—C16—H16	120.9
C8—C7—C5	119.1 (2)	C18—C17—C16	120.4 (3)
C9—C8—C7	119.0 (3)	C18—C17—H17	119.8
C9—C8—H8	120.5	C16—C17—H17	119.8
C7—C8—H8	120.5	O19—C18—C17	123.1 (3)
C8—C9—C10	121.1 (3)	O19—C18—C13	116.0 (3)
C8—C9—H9	119.5	C17—C18—C13	120.8 (3)
C10—C9—H9	119.5	C18—O19—C20	118.1 (3)
C9—C10—C11	120.6 (3)	O19—C20—H20A	109.5
C9—C10—H10	119.7	O19—C20—H20B	109.5
C11—C10—H10	119.7	H20A—C20—H20B	109.5
C12—C11—C10	118.6 (3)	O19—C20—H20C	109.5
C12—C11—C13	122.1 (2)	H20A—C20—H20C	109.5
C10—C11—C13	119.3 (2)	H20B—C20—H20C	109.5
C7—C12—C11	120.9 (2)

C5—O1—C2—N3	0.6 (3)	C10—C11—C12—C7	1.3 (4)
C5—O1—C2—N6	−178.7 (2)	C13—C11—C12—C7	−175.8 (3)
N6—C2—N3—N4	178.8 (3)	C12—C11—C13—C14	133.5 (3)
O1—C2—N3—N4	−0.4 (3)	C10—C11—C13—C14	−43.7 (4)
C2—N3—N4—C5	0.0 (3)	C12—C11—C13—C18	−45.5 (4)
N3—N4—C5—O1	0.4 (3)	C10—C11—C13—C18	137.3 (3)
N3—N4—C5—C7	178.7 (3)	C18—C13—C14—C15	−0.8 (4)
C2—O1—C5—N4	−0.6 (3)	C11—C13—C14—C15	−179.8 (2)
C2—O1—C5—C7	−179.2 (2)	C13—C14—C15—C16	1.0 (5)
N4—C5—C7—C12	165.3 (3)	C13—C14—C15—F15	−179.9 (3)
O1—C5—C7—C12	−16.4 (4)	F15—C15—C16—C17	179.4 (3)
N4—C5—C7—C8	−14.2 (5)	C14—C15—C16—C17	−1.6 (5)
O1—C5—C7—C8	164.1 (2)	C15—C16—C17—C18	1.9 (5)
C12—C7—C8—C9	2.8 (4)	C16—C17—C18—O19	−177.6 (3)
C5—C7—C8—C9	−177.7 (3)	C16—C17—C18—C13	−1.8 (5)
C7—C8—C9—C10	−1.6 (4)	C14—C13—C18—O19	177.3 (3)
C8—C9—C10—C11	0.3 (4)	C11—C13—C18—O19	−3.7 (4)
C9—C10—C11—C12	−0.1 (4)	C14—C13—C18—C17	1.2 (4)
C9—C10—C11—C13	177.2 (3)	C11—C13—C18—C17	−179.8 (3)
C8—C7—C12—C11	−2.7 (4)	C17—C18—O19—C20	−14.6 (4)
C5—C7—C12—C11	177.8 (3)	C13—C18—O19—C20	169.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N3ⁱ	0.86	2.13	2.972 (3)	166
N6—H6B···N4ⁱⁱ	0.86	2.29	3.118 (3)	161
C17—H17···Cg3ⁱⁱⁱ	0.93	2.72	3.53	146

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N3ⁱ	0.86	2.131	2.972 (3)	166
N6—H6B···N4ⁱⁱ	0.86	2.292	3.118 (3)	161
C17—H17···Cg3ⁱⁱⁱ	0.93	2.72	3.53	146

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2.

Acknowledgements

RK acknowledges the DST, New Delhi, for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. MKU thanks the DST, New Delhi, for the award of an INSPIRE Fellowship. VKG is thankful to the University of Jammu, Jammu, India, for financial support. DR acknowledges the UGC, New Delhi, for financial support under the Major Research Project- scheme [No. F.41-882/2012 (SR)].

References

Ainsworth, C. (1965). J. Am. Chem. Soc. 87, 5800–5803. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kulkarni, A. P., Tonzola, C. J., Babel, A. & Jenekhe, S. A. (2004). Chem. Mater. 16, 4556–4573. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Paik, K. L., Baek, N. S., Kim, H. K., Lee, J. H. & Lee, Y. (2002). Macromolecules, 35, 6782–6791. Web of Science CrossRef CAS 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
Zheng, J., Li, W., Song, M. & Xu, Y. (2012). Acta Cryst. E68, o1668. CSD CrossRef IUCr Journals 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1788

doi:10.1107/S1600536813031206

Open

access