(2-Chloro-8-meth­oxy­quinolin-3-yl)methanol monohydrate

Roopan, S.M.; Khan, F.N.; Kumar, A.S.; Hathwar, V.R.; Akkurt, M.

doi:10.1107/S1600536810020489

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1542

doi:10.1107/S1600536810020489

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(2-Chloro-8-methoxyquinolin-3-yl)methanol monohydrate

S. Mohana Roopan,^a F. Nawaz Khan,^a A. Sudheer Kumar,^a Venkatesha R. Hathwar ^b and Mehmet Akkurt ^c ^*

^aOrganic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 25 May 2010; accepted 29 May 2010; online 5 June 2010)

In the title compound, C₁₁H₁₀ClNO₂·H₂O, the organic molecule is roughly planar (r.m.s. deviation = 0.074 Å). In the crystal structure, molecues are linked by O—H⋯O and O—H⋯N hydrogen bonds and weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.578 (3) Å] consolidate the packing. A short Cl⋯O contact [3.147 (3) Å] is also observed.

Related literature

For further information on the starting material, see: Subashini et al. (2009 ). For general background to the title compound, see: Roopan et al. (2009 ). For related structures, see: Khan et al. (2010a ,b ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₀ClNO₂·H₂O
M_r = 241.67
Monoclinic, P 2₁ /n
a = 9.161 (5) Å
b = 14.246 (5) Å
c = 9.464 (5) Å
β = 116.819 (5)°
V = 1102.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 290 K
0.31 × 0.21 × 0.10 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton,England.]$ ) T_min = 0.903, T_max = 0.967
8360 measured reflections
2044 independent reflections
1212 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.134
S = 0.90
2044 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1–C3/C8/C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3ⁱ	0.82	1.90	2.705 (4)	165
O3—H1W⋯N1ⁱⁱ	0.85 (5)	2.17 (5)	2.988 (4)	163 (4)
O3—H2W⋯O1ⁱⁱⁱ	0.83 (4)	2.02 (4)	2.836 (4)	171 (5)
C10—H10B⋯Cg1ⁱ	0.97	2.93	3.738 (5)	142
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) x+1, y, z+1.

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton,England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton,England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020489/hb5469sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020489/hb5469Isup2.hkl

checkCIF report

Comment top

The importance and general background of the title compound is given in our earler paper (Roopan et al., 2009).

In the main molecule of the title compound (I), (Fig. 1), all the non-H atoms are roughly coplanar (r.m.s. deviation = 0.074 Å). The bond lengths and angles are comparable to the similar structures 2-chloro-3-hydroxymethyl-7,8-dimethylquinoline and 2-chloro-3-hydroxymethyl-6-methoxyquinoline (Khan et al., 2010a,b), and also those in literature (Allen et al., 1987).

The crystal structure is stabilized by intermolecular O—H···O and O—H···N interactions between the symmetry-related molecues (Table 1, Fig. 2). Adjacent molecules are stacked along the b axis through weak C—H···π interactions (Table 1) and π-π interactions [Cg1···Cg2(-x, 1 - y, -z) = 3.578 (3) Å, where Cg1 and Cg2 are centroids of the N1/C1–C3/C8/C9 and C4–C9 rings, respectively]. In addition a short Cl1.. O2 contact of 3.15 Å is also observed.

Related literature top

For further information on the starting material, see: Subashini et al. (2009). For general background to the title compound, see: Roopan et al. (2009). For related structures, see: Khan et al. (2010a,b). For bond-length data, see: Allen et al. (1987).

Experimental top

2-Chloro-8-methoxyquinoline-3-carbaldehyde (222 mg, 1 mmol), sodium borohydride (38 mg, 1 mmol) and catalytic amount of montmorillonite K-10 were taken in an open vessel and the resulting mixture was irradiated at 500 W for 5 min. Ethylacetate was poured into the reaction mixture and filtered off. The filtrated after removal of solvent was subjected to column chromatography packed with silica and ethyl acetate/petroleum ether was used as the eluant. Colourless slabs of (I) were grown by solvent evaporation from a solution of the compound in chloroform.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines. The H atoms not involved in hydrogen bonds have been omitted for clarity.

(2-Chloro-8-methoxyquinolin-3-yl)methanol monohydrate top

Crystal data top

C₁₁H₁₀ClNO₂·H₂O	F(000) = 504
M_r = 241.67	D_x = 1.456 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1021 reflections
a = 9.161 (5) Å	θ = 1.9–20.2°
b = 14.246 (5) Å	µ = 0.34 mm⁻¹
c = 9.464 (5) Å	T = 290 K
β = 116.819 (5)°	Slab, colourless
V = 1102.3 (9) Å³	0.31 × 0.21 × 0.10 mm
Z = 4

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	2044 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1212 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
ω scans	θ_max = 25.5°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→11
T_min = 0.903, T_max = 0.967	k = −17→17
8360 measured reflections	l = −11→11

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) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ²(F_o²) + (0.0692P)²] where P = (F_o² + 2F_c²)/3
2044 reflections	(Δ/σ)_max < 0.001
153 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₁H₁₀ClNO₂·H₂O	V = 1102.3 (9) Å³
M_r = 241.67	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.161 (5) Å	µ = 0.34 mm⁻¹
b = 14.246 (5) Å	T = 290 K
c = 9.464 (5) Å	0.31 × 0.21 × 0.10 mm
β = 116.819 (5)°

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	2044 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1212 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.967	R_int = 0.100
8360 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	Δρ_max = 0.40 e Å⁻³
2044 reflections	Δρ_min = −0.26 e Å⁻³
153 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Cl1	−0.12994 (10)	0.21700 (5)	−0.05478 (9)	0.0525 (3)
O1	0.0858 (3)	0.2656 (2)	−0.3822 (3)	0.0713 (10)
O2	0.1487 (3)	0.46372 (14)	0.3536 (2)	0.0515 (8)
N1	0.0521 (3)	0.35801 (15)	0.0948 (3)	0.0371 (8)
C1	0.0114 (4)	0.30580 (19)	−0.0297 (3)	0.0399 (10)
C2	0.0664 (4)	0.3140 (2)	−0.1453 (3)	0.0435 (10)
C3	0.1715 (4)	0.3870 (2)	−0.1243 (3)	0.0493 (11)
C4	0.3261 (4)	0.5254 (2)	0.0313 (4)	0.0558 (12)
C5	0.3720 (4)	0.5792 (2)	0.1620 (5)	0.0603 (14)
C6	0.3158 (4)	0.5601 (2)	0.2743 (4)	0.0545 (12)
C7	0.2105 (4)	0.4875 (2)	0.2525 (3)	0.0436 (10)
C8	0.1595 (3)	0.43029 (18)	0.1160 (3)	0.0379 (9)
C9	0.2198 (4)	0.4484 (2)	0.0056 (3)	0.0444 (11)
C10	0.0147 (4)	0.2459 (3)	−0.2813 (4)	0.0573 (11)
C11	0.2035 (5)	0.5135 (3)	0.4973 (4)	0.0678 (16)
O3	0.8868 (3)	0.3074 (2)	0.2937 (3)	0.0716 (10)
H1O	0.18120	0.24780	−0.34070	0.1070*
H3	0.21180	0.39630	−0.19750	0.0590*
H4	0.36470	0.53900	−0.04200	0.0670*
H5	0.44190	0.62970	0.17760	0.0730*
H6	0.35070	0.59720	0.36460	0.0660*
H10A	0.04510	0.18290	−0.23950	0.0690*
H10B	−0.10340	0.24780	−0.34210	0.0690*
H11A	0.32050	0.50900	0.55460	0.1020*
H11B	0.15520	0.48700	0.55960	0.1020*
H11C	0.17230	0.57820	0.47550	0.1020*
H1W	0.943 (5)	0.331 (3)	0.252 (5)	0.1080*
H2W	0.949 (6)	0.301 (3)	0.389 (5)	0.1080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0537 (5)	0.0487 (5)	0.0489 (5)	−0.0099 (4)	0.0176 (4)	−0.0054 (4)
O1	0.0644 (17)	0.112 (2)	0.0369 (13)	0.0262 (15)	0.0223 (13)	0.0030 (12)
O2	0.0555 (15)	0.0550 (14)	0.0428 (12)	−0.0026 (11)	0.0212 (11)	−0.0056 (10)
N1	0.0369 (14)	0.0372 (14)	0.0321 (13)	0.0029 (11)	0.0112 (11)	0.0046 (11)
C1	0.0379 (17)	0.0400 (17)	0.0342 (17)	0.0072 (14)	0.0096 (14)	0.0066 (13)
C2	0.0369 (17)	0.054 (2)	0.0324 (17)	0.0087 (15)	0.0094 (14)	0.0063 (13)
C3	0.047 (2)	0.067 (2)	0.0379 (18)	0.0167 (18)	0.0228 (16)	0.0161 (16)
C4	0.042 (2)	0.056 (2)	0.072 (2)	0.0051 (17)	0.0280 (18)	0.0169 (19)
C5	0.043 (2)	0.040 (2)	0.090 (3)	−0.0063 (16)	0.023 (2)	0.0051 (19)
C6	0.047 (2)	0.044 (2)	0.061 (2)	−0.0025 (16)	0.0141 (18)	−0.0045 (16)
C7	0.0358 (17)	0.0434 (18)	0.0448 (19)	0.0081 (15)	0.0122 (15)	0.0033 (14)
C8	0.0317 (16)	0.0343 (16)	0.0396 (16)	0.0055 (14)	0.0089 (14)	0.0054 (13)
C9	0.0380 (18)	0.0480 (19)	0.0458 (19)	0.0053 (15)	0.0176 (16)	0.0110 (15)
C10	0.056 (2)	0.076 (2)	0.0358 (19)	0.0121 (18)	0.0170 (17)	−0.0025 (16)
C11	0.071 (3)	0.078 (3)	0.046 (2)	0.000 (2)	0.019 (2)	−0.0121 (17)
O3	0.0575 (17)	0.108 (2)	0.0480 (15)	−0.0196 (15)	0.0226 (13)	0.0007 (15)

Geometric parameters (Å, º) top

Cl1—C1	1.748 (4)	C4—C9	1.413 (5)
O1—C10	1.406 (5)	C5—C6	1.401 (6)
O2—C7	1.356 (4)	C6—C7	1.365 (5)
O2—C11	1.410 (4)	C7—C8	1.417 (4)
O1—H1O	0.8200	C8—C9	1.409 (4)
O3—H1W	0.85 (5)	C3—H3	0.9300
O3—H2W	0.83 (4)	C4—H4	0.9300
N1—C1	1.298 (4)	C5—H5	0.9300
N1—C8	1.375 (4)	C6—H6	0.9300
C1—C2	1.401 (5)	C10—H10B	0.9700
C2—C3	1.369 (5)	C10—H10A	0.9700
C2—C10	1.507 (5)	C11—H11C	0.9600
C3—C9	1.408 (4)	C11—H11A	0.9600
C4—C5	1.351 (5)	C11—H11B	0.9600

Cl1···O2ⁱ	3.147 (3)

C7—O2—C11	118.3 (3)	C3—C9—C8	117.4 (3)
C10—O1—H1O	109.00	O1—C10—C2	112.8 (3)
H1W—O3—H2W	107 (5)	C2—C3—H3	119.00
C1—N1—C8	117.1 (3)	C9—C3—H3	119.00
Cl1—C1—N1	115.5 (3)	C5—C4—H4	120.00
Cl1—C1—C2	117.4 (2)	C9—C4—H4	120.00
N1—C1—C2	127.2 (3)	C6—C5—H5	120.00
C1—C2—C10	121.9 (3)	C4—C5—H5	119.00
C1—C2—C3	115.3 (3)	C7—C6—H6	120.00
C3—C2—C10	122.8 (3)	C5—C6—H6	120.00
C2—C3—C9	121.5 (3)	O1—C10—H10A	109.00
C5—C4—C9	120.2 (3)	C2—C10—H10A	109.00
C4—C5—C6	121.0 (3)	C2—C10—H10B	109.00
C5—C6—C7	120.6 (3)	O1—C10—H10B	109.00
O2—C7—C8	115.4 (3)	H10A—C10—H10B	108.00
C6—C7—C8	119.6 (3)	O2—C11—H11B	109.00
O2—C7—C6	125.0 (3)	O2—C11—H11C	110.00
N1—C8—C9	121.6 (2)	O2—C11—H11A	109.00
N1—C8—C7	118.9 (3)	H11A—C11—H11C	109.00
C7—C8—C9	119.5 (3)	H11B—C11—H11C	110.00
C3—C9—C4	123.6 (3)	H11A—C11—H11B	109.00
C4—C9—C8	119.0 (3)

C11—O2—C7—C6	−4.0 (5)	C2—C3—C9—C8	1.8 (5)
C11—O2—C7—C8	175.5 (3)	C9—C4—C5—C6	0.0 (6)
C8—N1—C1—Cl1	−178.2 (2)	C5—C4—C9—C3	−177.5 (3)
C8—N1—C1—C2	0.8 (5)	C5—C4—C9—C8	1.6 (5)
C1—N1—C8—C7	−178.4 (3)	C4—C5—C6—C7	−1.3 (6)
C1—N1—C8—C9	1.5 (4)	C5—C6—C7—O2	−179.7 (3)
Cl1—C1—C2—C3	177.3 (2)	C5—C6—C7—C8	0.9 (5)
Cl1—C1—C2—C10	−3.6 (4)	O2—C7—C8—N1	1.1 (4)
N1—C1—C2—C3	−1.7 (5)	O2—C7—C8—C9	−178.8 (3)
N1—C1—C2—C10	177.4 (3)	C6—C7—C8—N1	−179.3 (3)
C1—C2—C3—C9	0.3 (5)	C6—C7—C8—C9	0.8 (5)
C10—C2—C3—C9	−178.8 (3)	N1—C8—C9—C3	−2.7 (4)
C1—C2—C10—O1	−179.0 (3)	N1—C8—C9—C4	178.1 (3)
C3—C2—C10—O1	0.1 (5)	C7—C8—C9—C3	177.1 (3)
C2—C3—C9—C4	−179.1 (3)	C7—C8—C9—C4	−2.0 (4)

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1–C3/C8/C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3ⁱ	0.82	1.90	2.705 (4)	165
O3—H1W···N1ⁱⁱ	0.85 (5)	2.17 (5)	2.988 (4)	163 (4)
O3—H2W···O1ⁱⁱⁱ	0.83 (4)	2.02 (4)	2.836 (4)	171 (5)
C10—H10B···Cg1ⁱ	0.97	2.93	3.738 (5)	142

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀ClNO₂·H₂O
M_r	241.67
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	290
a, b, c (Å)	9.161 (5), 14.246 (5), 9.464 (5)
β (°)	116.819 (5)
V (Å³)	1102.3 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.31 × 0.21 × 0.10

Data collection
Diffractometer	Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.903, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	8360, 2044, 1212
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.134, 0.90
No. of reflections	2044
No. of parameters	153
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.26

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1–C3/C8/C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3ⁱ	0.82	1.90	2.705 (4)	165
O3—H1W···N1ⁱⁱ	0.85 (5)	2.17 (5)	2.988 (4)	163 (4)
O3—H2W···O1ⁱⁱⁱ	0.83 (4)	2.02 (4)	2.836 (4)	171 (5)
C10—H10B···Cg1ⁱ	0.97	2.93	3.738 (5)	142

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

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the FIST–DST program at SSCU, IISc. We also thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

References

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1542

doi:10.1107/S1600536810020489

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