3-(1H-Imidazol-1-yl)-1-phenyl­propan-1-ol

Fun, H.-K.; Quah, C.K.; Attia, M.I.; Abdel-Aziz, H.A.; Al-Rashood, K.A.

doi:10.1107/S1600536812004254

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o628

doi:10.1107/S1600536812004254

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3-(1H-Imidazol-1-yl)-1-phenylpropan-1-ol

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Mohamed I. Attia,^b Hatem A. Abdel-Aziz ^b and Khalid A. Al-Rashood ^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)

In the title compound, C₁₂H₁₄N₂O, the imidazole ring forms a dihedral angle of 66.73 (5)° with the phenyl ring. In the crystal, molecules are linked via O—H⋯N and C—H⋯O hydrogen bonds into sheets lying parallel to (100). The crystal structure is further consolidated by C—H⋯π interactions.

Related literature

For general background to and the pharmacological activities of the title compound, see: Latge (1999 ); Steenbergn & Casadevall (2000 ); Pacetti & Gelone (2003 ); Spellberg et al. (2006 ). For the preparation of the title compound, see: Aboul-Enein et al. (2011 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₂H₁₄N₂O
M_r = 202.25
Monoclinic, P 2₁ /c
a = 9.0352 (5) Å
b = 11.8521 (7) Å
c = 10.3462 (6) Å
β = 109.688 (1)°
V = 1043.17 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.34 × 0.26 × 0.19 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.972, T_max = 0.985
14426 measured reflections
3777 independent reflections
3245 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.125
S = 1.05
3777 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.26 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⋯N2ⁱ	0.964 (19)	1.89 (2)	2.8432 (12)	171.7 (17)
C1—H1B⋯O1ⁱⁱ	0.95	2.48	3.4188 (12)	172
C10—H10A⋯Cg1ⁱⁱⁱ	0.95	2.68	3.4778 (12)	142
C12—H12A⋯Cg1^iv	0.95	2.69	3.5373 (11)	149
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812004254/hb6620sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004254/hb6620Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004254/hb6620Isup3.cml

checkCIF report

Comment top

Over the past three decades, the incidence of both community-acquired and nosocomial invasive fungal infections has increased substantially. Clinically, candidosis, aspergillosis and cryptococcosis have been identified as three major opportunistic pathogens in the etiology of fungal infections in immune compromised patients (Latge, 1999; Steenbergn & Casadevall, 2000). Candida albicans accounts for the majority of invasive and superficial Candida infections (Pacetti & Gelone, 2003; Spellberg et al., 2006). Accordingly, the need for new antifungal drugs has prompted intensive research worldwide. The azole antifungal drugs constitute one of the major classes which are characterized by having the azole pharmacophoric moiety embedded in their structures. The title molecule exhibited anti-Candida activity (MIC = 10 µg/ml) and can serve as a prototypic molecule for subsequent molecular modifications.

In the title compound, Fig. 1, the imidazole ring (N1/N2/C10–C12, maximum deviation of 0.002 (1) Å at atoms N1 and C12) forms a dihedral angle of 66.73 (5)° with the phenyl ring (C1–C6).

In the crystal structure, Fig. 2, molecules are linked via intermolecular O1—H1O1···N2 and C1—H1B···O1 hydrogen bonds (Table 1) into two-dimensional networks parallel to (100). The crystal structure is further consolidated by C10—H10A···Cg1ⁱⁱⁱ and C12—H12A···Cg1^iv (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: Latge (1999); Steenbergn & Casadevall (2000); Pacetti & Gelone (2003); Spellberg et al. (2006). For the preparation of the title compound, see: Aboul-Enein et al. (2011). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

NaBH₄ (4.9 g, 0.13 mol) was added portion-wise to an ice cooled, stirred solution of 3-(1H-imidazol-1-yl)-1-phenylpropan-1-one (8.6 g, 0.043 mol) (Aboul-Enein et al., 2011) in methanol (100 ml). The mixture was stirred overnight at ambient temperature followed by evaporation of methanol under vacuum. The residue was dissolved in ethyl acetate (150 ml) and washed with water (3 × 50 ml). The organic layer was separated, dried (Na₂SO₄) and evaporated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as colourless blocks. M.p. = 380–382 K.

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 c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

3-(1H-Imidazol-1-yl)-1-phenylpropan-1-ol top

Crystal data top

C₁₂H₁₄N₂O	F(000) = 432
M_r = 202.25	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6547 reflections
a = 9.0352 (5) Å	θ = 3.0–32.6°
b = 11.8521 (7) Å	µ = 0.08 mm⁻¹
c = 10.3462 (6) Å	T = 100 K
β = 109.688 (1)°	Block, colourless
V = 1043.17 (10) Å³	0.34 × 0.26 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3777 independent reflections
Radiation source: fine-focus sealed tube	3245 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 32.6°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
T_min = 0.972, T_max = 0.985	k = −17→17
14426 measured reflections	l = −14→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0644P)² + 0.3608P] where P = (F_o² + 2F_c²)/3
3777 reflections	(Δ/σ)_max = 0.001
140 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₂H₁₄N₂O	V = 1043.17 (10) Å³
M_r = 202.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0352 (5) Å	µ = 0.08 mm⁻¹
b = 11.8521 (7) Å	T = 100 K
c = 10.3462 (6) Å	0.34 × 0.26 × 0.19 mm
β = 109.688 (1)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3777 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3245 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.985	R_int = 0.022
14426 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.67 e Å⁻³
3777 reflections	Δρ_min = −0.26 e Å⁻³
140 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	0.48286 (8)	0.08562 (6)	0.36457 (8)	0.02067 (16)
N1	0.25481 (8)	0.31589 (7)	0.35682 (8)	0.01420 (15)
N2	0.32358 (10)	0.45590 (7)	0.24613 (9)	0.02066 (17)
C1	0.31643 (10)	−0.13411 (8)	0.29554 (9)	0.01560 (16)
H1B	0.3689	−0.1285	0.3918	0.019*
C2	0.27877 (11)	−0.23971 (8)	0.23471 (10)	0.01808 (18)
H2B	0.3073	−0.3059	0.2892	0.022*
C3	0.19909 (12)	−0.24865 (8)	0.09354 (10)	0.01975 (18)
H3A	0.1735	−0.3208	0.0519	0.024*
C4	0.15757 (11)	−0.15146 (9)	0.01470 (9)	0.01935 (18)
H4A	0.1013	−0.1570	−0.0809	0.023*
C5	0.19809 (11)	−0.04577 (8)	0.07534 (9)	0.01624 (17)
H5A	0.1713	0.0203	0.0203	0.019*
C6	0.27760 (10)	−0.03610 (8)	0.21592 (9)	0.01380 (16)
C7	0.32242 (10)	0.07925 (8)	0.28116 (9)	0.01549 (16)
H7A	0.3017	0.1370	0.2066	0.019*
C8	0.22380 (10)	0.10796 (8)	0.37099 (9)	0.01587 (16)
H8A	0.1118	0.1116	0.3124	0.019*
H8B	0.2350	0.0464	0.4383	0.019*
C9	0.26905 (11)	0.21929 (8)	0.44836 (9)	0.01656 (17)
H9A	0.2007	0.2317	0.5044	0.020*
H9B	0.3789	0.2142	0.5117	0.020*
C10	0.37482 (11)	0.37408 (8)	0.33713 (10)	0.01860 (18)
H10A	0.4828	0.3579	0.3833	0.022*
C11	0.16177 (11)	0.44949 (8)	0.20509 (10)	0.01811 (18)
H11A	0.0914	0.4980	0.1397	0.022*
C12	0.11734 (10)	0.36343 (8)	0.27205 (9)	0.01602 (17)
H12A	0.0131	0.3411	0.2621	0.019*
H1O1	0.543 (2)	0.0448 (17)	0.3186 (19)	0.048 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0152 (3)	0.0220 (4)	0.0251 (3)	−0.0023 (2)	0.0071 (3)	−0.0072 (3)
N1	0.0142 (3)	0.0116 (3)	0.0184 (3)	0.0000 (2)	0.0076 (3)	−0.0010 (2)
N2	0.0182 (3)	0.0179 (4)	0.0290 (4)	0.0007 (3)	0.0120 (3)	0.0036 (3)
C1	0.0146 (3)	0.0167 (4)	0.0159 (3)	0.0024 (3)	0.0057 (3)	0.0012 (3)
C2	0.0204 (4)	0.0137 (4)	0.0232 (4)	0.0028 (3)	0.0114 (3)	0.0018 (3)
C3	0.0227 (4)	0.0154 (4)	0.0244 (4)	−0.0015 (3)	0.0121 (3)	−0.0055 (3)
C4	0.0207 (4)	0.0212 (4)	0.0160 (4)	−0.0009 (3)	0.0060 (3)	−0.0035 (3)
C5	0.0174 (4)	0.0158 (4)	0.0159 (4)	0.0010 (3)	0.0062 (3)	0.0007 (3)
C6	0.0125 (3)	0.0141 (4)	0.0160 (3)	−0.0003 (3)	0.0063 (3)	−0.0015 (3)
C7	0.0155 (3)	0.0142 (4)	0.0180 (4)	−0.0009 (3)	0.0072 (3)	−0.0011 (3)
C8	0.0176 (4)	0.0127 (4)	0.0205 (4)	−0.0004 (3)	0.0106 (3)	−0.0001 (3)
C9	0.0207 (4)	0.0135 (4)	0.0176 (4)	0.0012 (3)	0.0091 (3)	0.0003 (3)
C10	0.0141 (4)	0.0174 (4)	0.0262 (4)	−0.0003 (3)	0.0092 (3)	0.0014 (3)
C11	0.0176 (4)	0.0168 (4)	0.0219 (4)	0.0032 (3)	0.0092 (3)	0.0020 (3)
C12	0.0136 (3)	0.0160 (4)	0.0195 (4)	0.0003 (3)	0.0069 (3)	−0.0012 (3)

Geometric parameters (Å, º) top

O1—C7	1.4173 (11)	C4—H4A	0.9500
O1—H1O1	0.97 (2)	C5—C6	1.3931 (12)
N1—C10	1.3571 (11)	C5—H5A	0.9500
N1—C12	1.3767 (11)	C6—C7	1.5180 (12)
N1—C9	1.4636 (12)	C7—C8	1.5269 (12)
N2—C10	1.3218 (13)	C7—H7A	1.0000
N2—C11	1.3802 (12)	C8—C9	1.5260 (13)
C1—C2	1.3907 (13)	C8—H8A	0.9900
C1—C6	1.3986 (12)	C8—H8B	0.9900
C1—H1B	0.9500	C9—H9A	0.9900
C2—C3	1.3979 (14)	C9—H9B	0.9900
C2—H2B	0.9500	C10—H10A	0.9500
C3—C4	1.3881 (14)	C11—C12	1.3671 (13)
C3—H3A	0.9500	C11—H11A	0.9500
C4—C5	1.3936 (13)	C12—H12A	0.9500

C7—O1—H1O1	107.8 (11)	C6—C7—C8	110.39 (7)
C10—N1—C12	106.94 (8)	O1—C7—H7A	108.7
C10—N1—C9	126.45 (8)	C6—C7—H7A	108.7
C12—N1—C9	126.60 (7)	C8—C7—H7A	108.7
C10—N2—C11	105.03 (8)	C9—C8—C7	113.82 (7)
C2—C1—C6	120.42 (8)	C9—C8—H8A	108.8
C2—C1—H1B	119.8	C7—C8—H8A	108.8
C6—C1—H1B	119.8	C9—C8—H8B	108.8
C1—C2—C3	120.16 (9)	C7—C8—H8B	108.8
C1—C2—H2B	119.9	H8A—C8—H8B	107.7
C3—C2—H2B	119.9	N1—C9—C8	112.79 (7)
C4—C3—C2	119.55 (9)	N1—C9—H9A	109.0
C4—C3—H3A	120.2	C8—C9—H9A	109.0
C2—C3—H3A	120.2	N1—C9—H9B	109.0
C3—C4—C5	120.22 (8)	C8—C9—H9B	109.0
C3—C4—H4A	119.9	H9A—C9—H9B	107.8
C5—C4—H4A	119.9	N2—C10—N1	111.96 (8)
C6—C5—C4	120.59 (8)	N2—C10—H10A	124.0
C6—C5—H5A	119.7	N1—C10—H10A	124.0
C4—C5—H5A	119.7	C12—C11—N2	110.28 (8)
C5—C6—C1	119.04 (8)	C12—C11—H11A	124.9
C5—C6—C7	120.32 (8)	N2—C11—H11A	124.9
C1—C6—C7	120.64 (8)	C11—C12—N1	105.80 (8)
O1—C7—C6	112.55 (7)	C11—C12—H12A	127.1
O1—C7—C8	107.72 (7)	N1—C12—H12A	127.1

C6—C1—C2—C3	−1.16 (13)	O1—C7—C8—C9	52.81 (10)
C1—C2—C3—C4	−0.15 (14)	C6—C7—C8—C9	176.07 (7)
C2—C3—C4—C5	1.41 (14)	C10—N1—C9—C8	−107.01 (10)
C3—C4—C5—C6	−1.37 (14)	C12—N1—C9—C8	71.41 (11)
C4—C5—C6—C1	0.06 (13)	C7—C8—C9—N1	59.04 (10)
C4—C5—C6—C7	179.56 (8)	C11—N2—C10—N1	−0.15 (11)
C2—C1—C6—C5	1.20 (12)	C12—N1—C10—N2	0.31 (11)
C2—C1—C6—C7	−178.30 (8)	C9—N1—C10—N2	178.99 (8)
C5—C6—C7—O1	−129.62 (8)	C10—N2—C11—C12	−0.07 (11)
C1—C6—C7—O1	49.88 (10)	N2—C11—C12—N1	0.25 (11)
C5—C6—C7—C8	109.98 (9)	C10—N1—C12—C11	−0.33 (10)
C1—C6—C7—C8	−70.52 (10)	C9—N1—C12—C11	−179.01 (8)

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···N2ⁱ	0.964 (19)	1.89 (2)	2.8432 (12)	171.7 (17)
C1—H1B···O1ⁱⁱ	0.95	2.48	3.4188 (12)	172
C10—H10A···Cg1ⁱⁱⁱ	0.95	2.68	3.4778 (12)	142
C12—H12A···Cg1^iv	0.95	2.69	3.5373 (11)	149

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₂O
M_r	202.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.0352 (5), 11.8521 (7), 10.3462 (6)
β (°)	109.688 (1)
V (Å³)	1043.17 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.34 × 0.26 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.972, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	14426, 3777, 3245
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.125, 1.05
No. of reflections	3777
No. of parameters	140
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.26

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···N2ⁱ	0.964 (19)	1.89 (2)	2.8432 (12)	171.7 (17)
C1—H1B···O1ⁱⁱ	0.95	2.48	3.4188 (12)	172
C10—H10A···Cg1ⁱⁱⁱ	0.95	2.68	3.4778 (12)	142
C12—H12A···Cg1^iv	0.95	2.69	3.5373 (11)	149

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160) and the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, for supporting this study.

References

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Volume 68| Part 3| March 2012| Page o628

doi:10.1107/S1600536812004254

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