(E)-N-[3-(Imidazol-1-yl)-1-phenyl­propyl­idene]hydroxyl­amine

Fun, H.-K.; Quah, C.K.; Attia, M.I.; Almutairi, M.S.; Ghoneim, S.W.

doi:10.1107/S1600536812004266

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o627

doi:10.1107/S1600536812004266

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(E)-N-[3-(Imidazol-1-yl)-1-phenylpropylidene]hydroxylamine

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Mohamed I. Attia,^b ¶ Maha S. Almutairi ^b and Soraya W. Ghoneim ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 31 January 2012; accepted 1 February 2012; online 10 February 2012)

The title compound, C₁₂H₁₃N₃O, exists in an E configuration with respect to the C=N bond [1.285 (2) Å]. The imidazole ring forms a dihedral angle of 75.97 (10)° with the phenyl ring. In the crystal, molecules are linked via O—H⋯N and C—H⋯N hydrogen bonds into sheets lying parallel to (001). The crystal structure also features C—H⋯π interactions.

Related literature

For general background to and the pharmacological activities of the title compound, see: Weinberg (1996 ); Wildfeuer et al. (1998 ); Georgopapadakou (1998 ). For standard bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₂H₁₃N₃O
M_r = 215.25
Monoclinic, P 2₁ /c
a = 8.0990 (1) Å
b = 14.0513 (2) Å
c = 9.9771 (2) Å
β = 93.058 (1)°
V = 1133.79 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.35 × 0.18 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.972, T_max = 0.991
12642 measured reflections
3300 independent reflections
2653 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.138
S = 1.13
3300 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N3ⁱ	0.90 (3)	1.82 (3)	2.712 (2)	176 (3)
C2—H2A⋯N1ⁱⁱ	0.95	2.56	3.477 (2)	162
C12—H12A⋯Cg1ⁱⁱⁱ	0.95	2.74	3.558 (2)	145
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812004266/hb6619sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004266/hb6619Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004266/hb6619Isup3.cml

checkCIF report

Comment top

A significant increase in fungal infections has been observed over the past three decades. Many reports of invasive topical and systemic infections caused by the opportunistic pathogen Candida species are always associated with the use of broad-spectrum antibiotics, immunosuppressive agents, anticancer and anti-AIDS drugs (Weinberg, 1996). One of the major problems in the treatment of Candida infections is the spread of antifungal drug resistance mainly in patients chronically subjected to antimycotic therapy such as HIV-infected patients (Wildfeuer et al., 1998; Georgopapadakou, 1998). Azoles are commonly used as antifungal agent specially for Candida infections as many marketed drugs contain the azole moiety. The title compound contains the azole moiety and it was prepared to test its antifungal potential and will be further elaborated to other azole-containing new bioactive chemical entities.

In the title compound, Fig.1, the imidazole ring (N2/N3/C10-C12, maximum deviation of 0.001 (2) Å at atoms N3, C11 and C12) forms a dihedral angle of 75.97 (10)° with the phenyl ring (C1-C6). Bond lengths (Allen et al., 1987) and angles are within normal ranges. The title compound exists in trans configuration with respect to the C7═N1 bond [1.285 (2) Å].

In the crystal structure, Fig. 2, molecules are linked via intermolecular O1–H1O1···N3 and C2–H2A···N1 hydrogen bonds (Table 1) into two-dimensional networks parallel to (001). The crystal structure is further consolidated by C12–H12A···Cg1ⁱⁱⁱ (Table 1) interactions, where Cg1 is the centroid of C1-C6 phenyl ring.

Related literature top

For general background to and the pharmacological activities of the title compound, see: Weinberg (1996); Wildfeuer et al. (1998); Georgopapadakou (1998). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 3-(1H-imidazol-1-yl)-1-phenylpropan-1-one (0.02 g, 0.1 mmol), hydroxylamine hydrochloride (0.14 g, 0.2 mol), and KOH (0.112 g, 0.2 mmol) in ethanol (10 ml) was refluxed under stirring for 18h. The reaction mixture was allowed to cool to room temperature and the insolubles were removed by filtration. The filtrate was evaporated under vacuum and the residue was suspended in water (10 ml), filtered, dried and recrystallized from ethanol to yield colourless blocks of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

(E)-N-[3-(Imidazol-1-yl)-1-phenylpropylidene]hydroxylamine top

Crystal data top

C₁₂H₁₃N₃O	F(000) = 456
M_r = 215.25	D_x = 1.261 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5276 reflections
a = 8.0990 (1) Å	θ = 2.5–30.1°
b = 14.0513 (2) Å	µ = 0.08 mm⁻¹
c = 9.9771 (2) Å	T = 100 K
β = 93.058 (1)°	Block, colourless
V = 1133.79 (3) Å³	0.35 × 0.18 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3300 independent reflections
Radiation source: fine-focus sealed tube	2653 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 30.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→11
T_min = 0.972, T_max = 0.991	k = −18→19
12642 measured reflections	l = −14→14

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0228P)² + 1.5032P] where P = (F_o² + 2F_c²)/3
3300 reflections	(Δ/σ)_max = 0.001
149 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₂H₁₃N₃O	V = 1133.79 (3) Å³
M_r = 215.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0990 (1) Å	µ = 0.08 mm⁻¹
b = 14.0513 (2) Å	T = 100 K
c = 9.9771 (2) Å	0.35 × 0.18 × 0.11 mm
β = 93.058 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3300 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2653 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.991	R_int = 0.026
12642 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.36 e Å⁻³
3300 reflections	Δρ_min = −0.29 e Å⁻³
149 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.35159 (18)	1.05298 (10)	0.16643 (14)	0.0222 (3)
N1	0.2389 (2)	1.00261 (11)	0.24156 (16)	0.0190 (3)
N2	0.37457 (19)	0.78810 (11)	0.03621 (15)	0.0155 (3)
N3	0.4790 (2)	0.66854 (12)	0.15734 (17)	0.0242 (4)
C1	−0.0041 (2)	0.79271 (13)	0.20420 (18)	0.0185 (4)
H1A	0.0470	0.7650	0.1301	0.022*
C2	−0.1123 (2)	0.73889 (14)	0.27705 (19)	0.0212 (4)
H2A	−0.1339	0.6745	0.2529	0.025*
C3	−0.1888 (2)	0.77890 (14)	0.38485 (19)	0.0223 (4)
H3A	−0.2612	0.7417	0.4354	0.027*
C4	−0.1592 (2)	0.87348 (14)	0.41854 (19)	0.0215 (4)
H4A	−0.2131	0.9014	0.4911	0.026*
C5	−0.0509 (2)	0.92730 (14)	0.34644 (19)	0.0195 (4)
H5A	−0.0313	0.9920	0.3700	0.023*
C6	0.0299 (2)	0.88731 (13)	0.23934 (18)	0.0154 (3)
C7	0.1555 (2)	0.94228 (12)	0.16866 (17)	0.0144 (3)
C8	0.1779 (2)	0.92702 (13)	0.02083 (18)	0.0164 (4)
H8A	0.1631	0.9888	−0.0259	0.020*
H8B	0.0896	0.8838	−0.0150	0.020*
C9	0.3457 (2)	0.88532 (13)	−0.01285 (18)	0.0177 (4)
H9A	0.3536	0.8858	−0.1115	0.021*
H9B	0.4344	0.9270	0.0261	0.021*
C10	0.4732 (2)	0.76180 (14)	0.14318 (19)	0.0197 (4)
H10A	0.5315	0.8053	0.2013	0.024*
C11	0.3783 (3)	0.63328 (14)	0.0532 (2)	0.0256 (4)
H11A	0.3577	0.5677	0.0365	0.031*
C12	0.3129 (3)	0.70599 (14)	−0.0221 (2)	0.0233 (4)
H12A	0.2396	0.7011	−0.0994	0.028*
H1O1	0.403 (3)	1.0915 (19)	0.227 (3)	0.037 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0233 (7)	0.0180 (7)	0.0258 (7)	−0.0076 (6)	0.0066 (6)	−0.0048 (6)
N1	0.0181 (8)	0.0159 (7)	0.0232 (8)	−0.0006 (6)	0.0033 (6)	−0.0019 (6)
N2	0.0154 (7)	0.0140 (7)	0.0169 (7)	0.0004 (6)	0.0004 (6)	−0.0012 (6)
N3	0.0239 (9)	0.0225 (9)	0.0261 (9)	0.0041 (7)	0.0016 (7)	0.0042 (7)
C1	0.0178 (9)	0.0193 (9)	0.0181 (8)	−0.0008 (7)	−0.0018 (7)	−0.0015 (7)
C2	0.0223 (9)	0.0185 (9)	0.0221 (9)	−0.0049 (7)	−0.0049 (7)	0.0010 (7)
C3	0.0201 (9)	0.0263 (10)	0.0204 (9)	−0.0036 (8)	0.0003 (7)	0.0064 (8)
C4	0.0199 (9)	0.0263 (10)	0.0185 (9)	0.0017 (8)	0.0023 (7)	0.0015 (7)
C5	0.0195 (9)	0.0184 (9)	0.0205 (9)	0.0012 (7)	−0.0001 (7)	−0.0014 (7)
C6	0.0143 (8)	0.0163 (8)	0.0149 (8)	0.0010 (7)	−0.0041 (6)	0.0017 (6)
C7	0.0145 (8)	0.0121 (8)	0.0163 (8)	0.0038 (6)	−0.0013 (6)	0.0021 (6)
C8	0.0176 (9)	0.0160 (8)	0.0152 (8)	0.0024 (7)	−0.0021 (7)	0.0029 (6)
C9	0.0205 (9)	0.0148 (8)	0.0179 (8)	0.0014 (7)	0.0030 (7)	0.0021 (7)
C10	0.0207 (9)	0.0190 (9)	0.0191 (9)	0.0026 (7)	−0.0017 (7)	−0.0009 (7)
C11	0.0258 (10)	0.0177 (9)	0.0338 (11)	−0.0002 (8)	0.0057 (9)	−0.0026 (8)
C12	0.0252 (10)	0.0197 (9)	0.0244 (9)	−0.0019 (8)	−0.0044 (8)	−0.0043 (8)

Geometric parameters (Å, º) top

O1—N1	1.403 (2)	C4—C5	1.388 (3)
O1—H1O1	0.90 (3)	C4—H4A	0.9500
N1—C7	1.285 (2)	C5—C6	1.400 (3)
N2—C10	1.350 (2)	C5—H5A	0.9500
N2—C12	1.374 (2)	C6—C7	1.485 (3)
N2—C9	1.466 (2)	C7—C8	1.511 (2)
N3—C10	1.319 (3)	C8—C9	1.534 (3)
N3—C11	1.378 (3)	C8—H8A	0.9900
C1—C2	1.391 (3)	C8—H8B	0.9900
C1—C6	1.398 (3)	C9—H9A	0.9900
C1—H1A	0.9500	C9—H9B	0.9900
C2—C3	1.389 (3)	C10—H10A	0.9500
C2—H2A	0.9500	C11—C12	1.359 (3)
C3—C4	1.389 (3)	C11—H11A	0.9500
C3—H3A	0.9500	C12—H12A	0.9500

N1—O1—H1O1	103.3 (17)	N1—C7—C6	115.28 (16)
C7—N1—O1	111.57 (15)	N1—C7—C8	124.02 (17)
C10—N2—C12	106.95 (16)	C6—C7—C8	120.70 (15)
C10—N2—C9	126.60 (15)	C7—C8—C9	114.95 (15)
C12—N2—C9	126.38 (16)	C7—C8—H8A	108.5
C10—N3—C11	105.09 (17)	C9—C8—H8A	108.5
C2—C1—C6	120.45 (18)	C7—C8—H8B	108.5
C2—C1—H1A	119.8	C9—C8—H8B	108.5
C6—C1—H1A	119.8	H8A—C8—H8B	107.5
C3—C2—C1	120.27 (18)	N2—C9—C8	114.23 (15)
C3—C2—H2A	119.9	N2—C9—H9A	108.7
C1—C2—H2A	119.9	C8—C9—H9A	108.7
C4—C3—C2	119.75 (18)	N2—C9—H9B	108.7
C4—C3—H3A	120.1	C8—C9—H9B	108.7
C2—C3—H3A	120.1	H9A—C9—H9B	107.6
C5—C4—C3	120.14 (18)	N3—C10—N2	111.89 (17)
C5—C4—H4A	119.9	N3—C10—H10A	124.1
C3—C4—H4A	119.9	N2—C10—H10A	124.1
C4—C5—C6	120.72 (18)	C12—C11—N3	110.14 (18)
C4—C5—H5A	119.6	C12—C11—H11A	124.9
C6—C5—H5A	119.6	N3—C11—H11A	124.9
C1—C6—C5	118.63 (17)	C11—C12—N2	105.94 (17)
C1—C6—C7	120.40 (16)	C11—C12—H12A	127.0
C5—C6—C7	120.90 (16)	N2—C12—H12A	127.0

C6—C1—C2—C3	0.5 (3)	C5—C6—C7—C8	−147.91 (17)
C1—C2—C3—C4	1.1 (3)	N1—C7—C8—C9	66.1 (2)
C2—C3—C4—C5	−1.3 (3)	C6—C7—C8—C9	−114.85 (18)
C3—C4—C5—C6	−0.1 (3)	C10—N2—C9—C8	−104.3 (2)
C2—C1—C6—C5	−1.9 (3)	C12—N2—C9—C8	79.3 (2)
C2—C1—C6—C7	175.03 (17)	C7—C8—C9—N2	65.6 (2)
C4—C5—C6—C1	1.7 (3)	C11—N3—C10—N2	0.1 (2)
C4—C5—C6—C7	−175.24 (17)	C12—N2—C10—N3	0.0 (2)
O1—N1—C7—C6	−178.52 (14)	C9—N2—C10—N3	−176.95 (17)
O1—N1—C7—C8	0.6 (2)	C10—N3—C11—C12	−0.1 (2)
C1—C6—C7—N1	−145.59 (17)	N3—C11—C12—N2	0.1 (2)
C5—C6—C7—N1	31.3 (2)	C10—N2—C12—C11	−0.1 (2)
C1—C6—C7—C8	35.2 (2)	C9—N2—C12—C11	176.87 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N3ⁱ	0.90 (3)	1.82 (3)	2.712 (2)	176 (3)
C2—H2A···N1ⁱⁱ	0.95	2.56	3.477 (2)	162
C12—H12A···Cg1ⁱⁱⁱ	0.95	2.74	3.558 (2)	145

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃N₃O
M_r	215.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.0990 (1), 14.0513 (2), 9.9771 (2)
β (°)	93.058 (1)
V (Å³)	1133.79 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.18 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.972, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	12642, 3300, 2653
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.138, 1.13
No. of reflections	3300
No. of parameters	149
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.29

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N3ⁱ	0.90 (3)	1.82 (3)	2.712 (2)	176 (3)
C2—H2A···N1ⁱⁱ	0.95	2.56	3.477 (2)	162
C12—H12A···Cg1ⁱⁱⁱ	0.95	2.74	3.558 (2)	145

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

¶Additional correspondence author, e-mail: mattia@ksu.edu.sa.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia (USM) for a Research University Grant (grant No. 1001/PFIZIK/811160). This research project was supported by a grant from the research center of the center of female scientific and medical colleges in King Saud University.

References

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Volume 68| Part 3| March 2012| Page o627

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