4-[(9-Ethyl-9H-carbazol-3-yl)imino­meth­yl]phenol

Lin, S.; Jia, R.; Gao, X.; Yu, H.; Yuan, Y.

doi:10.1107/S1600536810046167

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3194

https://doi.org/10.1107/S1600536810046167

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4-[(9-Ethyl-9H-carbazol-3-yl)iminomethyl]phenol

Songzhu Lin,^a ^* Ruokun Jia,^a Xiaoli Gao,^a Haihui Yu ^a and Yanlin Yuan ^a

^aNortheast China Electric Power University Personnel, Jilin 132012, People's Republic of China
^*Correspondence e-mail: songzhulin@hotmail.com

(Received 14 October 2010; accepted 9 November 2010; online 17 November 2010)

In the title compound, C₂₁H₁₈N₂O, the dihedral angle between the phenol ring and the carbazole system is 39.34 (2)°. Intermolecular O—H⋯N hydrogen bonds and C—H⋯π and π–π interactions [centroid–centroid distances = 3.426 (2) and 3.768 (2) Å] stabilize the crystal structure.

Related literature

For polar organic molecules as components of non-linear optical, electro-optical, photorefractive and optical-limiting materials, see: Nalwa & Miyata (1997 ); Kuzyk & Dirk (1998 ); Nesterov et al. (2002 ).

Experimental

Crystal data

C₂₁H₁₈N₂O
M_r = 314.37
Orthorhombic, P b c a
a = 13.386 (6) Å
b = 9.247 (4) Å
c = 26.443 (10) Å
V = 3273 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
21605 measured reflections
2878 independent reflections
1615 reflections with I > 2σ(I)
R_int = 0.081
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.140
S = 1.02
2878 reflections
218 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, °)

Cg2 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.82	2.09	2.842 (3)	153
C1—H1A⋯Cg2ⁱⁱ	0.96	2.77	3.698 (2)	162
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810046167/vm2053sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046167/vm2053Isup2.hkl

checkCIF report

Comment top

Polar organic molecules as components of NLO, electro-optical, photorefractive and optical-limiting materials have been under intensive investigation (Nalwa & Miyata, 1997; Kuzyk & Dirk, 1998; Nesterov et al., 2002). Many N-ethylcarbazole derivatives have been studied for this purpose. In this paper, we describe the synthesis and structure determination of the title compound.

In the title compound, atoms O1, C15, N2 lie in the plane of phenyl ring C16—C21 (p1) with the largest deviation of 0.002 (3) Å for C16. The atoms of the carbazole ring together with C2 and N2 form a plane (p2) for which the largest deviation is 0.068 (1) Å for C5. The fragment C11,N2, C15,C16,C17 is coplanar (p3). The dihedral angles formed by p1 with p2 and p3 are 39.34 (2) and 6.01 (2)°, respectively. The dihedral angle between p2 and p3 is 42.21 (3)°.

In the lattice, π–π and C—H···π interactions occur [Cg1···Cg1ⁱ = 3.426 (2), Cg2···Cg3ⁱ = 3.768 (2) Å, C1···Cg2ⁱⁱ = 3.698 (2) Å, H1A···Cg2ⁱⁱ = 2.77 Å, symmetry codes: ⁱ 1 - x, -y, 1 - z; ⁱⁱ 3/2 - x, -1/2 + y, z. Cg1, Cg2, Cg3 refer to ring N1—C3—C8—C9—C14 and phenyl rings C3—C8 and C9—C14, respectively]. In addition, an intermolecular hydrogen bond (Table 1) along with the C—H···π and π–π interactions stabilizes the crystal structure. The H-bond results in infinite chains along [010].

Related literature top

Experimental top

The title compound was synthesized by reaction of 9-ethyl-carbazol-3-amine (0.420 g, 0.002 mol) and 4-hydroxybenzaldehyde (0.244 g, 0.002 mol) in ethanol (50 ml) under stirring for 5 h at room temperature. Single crystals suitable for x-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

Structure description top

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

4-[(9-Ethyl-9H-carbazol-3-yl)iminomethyl]phenol top

Crystal data top

C₂₁H₁₈N₂O	F(000) = 1328
M_r = 314.37	D_x = 1.276 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 13.386 (6) Å	θ = 4–14°
b = 9.247 (4) Å	µ = 0.08 mm⁻¹
c = 26.443 (10) Å	T = 295 K
V = 3273 (2) Å³	Block, brown
Z = 8	0.25 × 0.20 × 0.15 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.081
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 1.5°
Graphite monochromator	h = −15→15
ω scans	k = −10→10
21605 measured reflections	l = −31→28
2878 independent reflections	3 standard reflections every 100 reflections
1615 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0568P)² + 0.6129P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2878 reflections	Δρ_max = 0.18 e Å⁻³
218 parameters	Δρ_min = −0.18 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: 0.0037 (8)

Crystal data top

C₂₁H₁₈N₂O	V = 3273 (2) Å³
M_r = 314.37	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.386 (6) Å	µ = 0.08 mm⁻¹
b = 9.247 (4) Å	T = 295 K
c = 26.443 (10) Å	0.25 × 0.20 × 0.15 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.081
21605 measured reflections	3 standard reflections every 100 reflections
2878 independent reflections	intensity decay: none
1615 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
2878 reflections	Δρ_min = −0.18 e Å⁻³
218 parameters

Special details top

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	0.61757 (15)	0.7932 (2)	0.83217 (7)	0.0802 (7)
H1	0.5624	0.8316	0.8314	0.096*
N1	0.64140 (15)	0.0252 (2)	0.47293 (8)	0.0538 (6)
N2	0.58786 (17)	0.3455 (2)	0.64785 (8)	0.0580 (6)
C1	0.7978 (2)	−0.0332 (4)	0.42951 (13)	0.0866 (10)
H1A	0.8397	−0.1123	0.4193	0.130*
H1B	0.8343	0.0292	0.4519	0.130*
H1C	0.7772	0.0202	0.4002	0.130*
C2	0.7074 (2)	−0.0908 (3)	0.45633 (11)	0.0639 (8)
H2B	0.6711	−0.1547	0.4338	0.077*
H2C	0.7285	−0.1468	0.4855	0.077*
C3	0.57518 (18)	0.0966 (3)	0.44114 (10)	0.0509 (7)
C4	0.5568 (2)	0.0753 (3)	0.39037 (11)	0.0635 (8)
H4A	0.5892	0.0024	0.3725	0.076*
C5	0.4897 (2)	0.1644 (3)	0.36707 (12)	0.0710 (9)
H5A	0.4767	0.1523	0.3328	0.085*
C6	0.4407 (2)	0.2721 (3)	0.39335 (12)	0.0692 (8)
H6A	0.3953	0.3310	0.3765	0.083*
C7	0.45795 (19)	0.2937 (3)	0.44390 (11)	0.0605 (7)
H7A	0.4241	0.3658	0.4614	0.073*
C8	0.52679 (18)	0.2060 (3)	0.46856 (10)	0.0473 (6)
C9	0.56752 (17)	0.2025 (3)	0.51875 (9)	0.0462 (6)
C10	0.55122 (17)	0.2834 (3)	0.56227 (10)	0.0509 (7)
H10A	0.5030	0.3558	0.5624	0.061*
C11	0.60673 (19)	0.2563 (3)	0.60528 (10)	0.0518 (7)
C12	0.6761 (2)	0.1429 (3)	0.60559 (10)	0.0576 (7)
H12A	0.7122	0.1242	0.6349	0.069*
C13	0.69205 (19)	0.0585 (3)	0.56350 (11)	0.0579 (7)
H13A	0.7376	−0.0174	0.5642	0.069*
C14	0.63826 (18)	0.0899 (3)	0.51982 (10)	0.0492 (7)
C15	0.6605 (2)	0.3883 (3)	0.67601 (11)	0.0613 (8)
H15A	0.7244	0.3539	0.6692	0.074*
C16	0.6471 (2)	0.4883 (3)	0.71814 (10)	0.0593 (7)
C17	0.7279 (2)	0.5339 (3)	0.74665 (11)	0.0716 (9)
H17A	0.7907	0.4947	0.7404	0.086*
C18	0.7171 (2)	0.6370 (4)	0.78447 (11)	0.0741 (9)
H18A	0.7724	0.6675	0.8029	0.089*
C19	0.6242 (2)	0.6938 (3)	0.79452 (10)	0.0624 (8)
C20	0.5425 (2)	0.6490 (3)	0.76697 (11)	0.0685 (8)
H20A	0.4795	0.6866	0.7739	0.082*
C21	0.5548 (2)	0.5481 (3)	0.72916 (11)	0.0684 (8)
H21A	0.4994	0.5192	0.7105	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0871 (15)	0.0854 (15)	0.0680 (13)	−0.0061 (12)	0.0009 (11)	−0.0171 (12)
N1	0.0561 (13)	0.0473 (13)	0.0581 (15)	0.0069 (11)	0.0047 (11)	−0.0006 (11)
N2	0.0668 (15)	0.0555 (14)	0.0516 (14)	0.0026 (12)	0.0064 (12)	0.0043 (12)
C1	0.0619 (19)	0.094 (2)	0.104 (3)	0.0178 (18)	0.0165 (18)	0.007 (2)
C2	0.0691 (18)	0.0502 (17)	0.072 (2)	0.0120 (15)	0.0020 (15)	−0.0050 (15)
C3	0.0504 (15)	0.0465 (15)	0.0558 (18)	−0.0040 (13)	0.0049 (14)	0.0011 (14)
C4	0.0670 (18)	0.0630 (19)	0.061 (2)	0.0038 (16)	0.0000 (15)	−0.0093 (16)
C5	0.074 (2)	0.080 (2)	0.0587 (19)	0.0030 (18)	−0.0070 (16)	−0.0039 (17)
C6	0.0697 (19)	0.073 (2)	0.065 (2)	0.0118 (16)	−0.0099 (16)	0.0089 (17)
C7	0.0571 (17)	0.0580 (18)	0.066 (2)	0.0058 (14)	0.0018 (15)	0.0063 (16)
C8	0.0452 (14)	0.0447 (15)	0.0521 (17)	−0.0003 (12)	0.0060 (12)	0.0034 (13)
C9	0.0459 (14)	0.0403 (14)	0.0524 (17)	0.0001 (12)	0.0066 (12)	0.0055 (13)
C10	0.0479 (15)	0.0446 (15)	0.0601 (17)	0.0040 (12)	0.0078 (14)	0.0049 (14)
C11	0.0564 (16)	0.0490 (16)	0.0499 (17)	0.0001 (13)	0.0109 (14)	0.0028 (14)
C12	0.0619 (17)	0.0568 (17)	0.0540 (18)	0.0030 (15)	−0.0014 (14)	0.0062 (15)
C13	0.0585 (17)	0.0518 (16)	0.0633 (19)	0.0102 (13)	−0.0003 (15)	0.0057 (15)
C14	0.0484 (15)	0.0434 (15)	0.0557 (18)	−0.0011 (13)	0.0075 (13)	0.0001 (14)
C15	0.0726 (19)	0.0539 (17)	0.0573 (18)	0.0054 (16)	0.0096 (16)	0.0085 (15)
C16	0.0678 (19)	0.0598 (18)	0.0502 (18)	0.0014 (15)	0.0049 (15)	0.0060 (14)
C17	0.063 (2)	0.081 (2)	0.071 (2)	0.0010 (17)	0.0020 (16)	0.0031 (19)
C18	0.072 (2)	0.087 (2)	0.063 (2)	−0.0078 (18)	−0.0039 (16)	−0.0078 (18)
C19	0.075 (2)	0.0636 (18)	0.0484 (17)	−0.0049 (17)	0.0060 (16)	0.0014 (15)
C20	0.069 (2)	0.075 (2)	0.0622 (19)	0.0049 (16)	0.0005 (16)	−0.0105 (17)
C21	0.068 (2)	0.078 (2)	0.0593 (19)	0.0006 (17)	0.0005 (15)	−0.0099 (17)

Geometric parameters (Å, º) top

O1—C19	1.358 (3)	C8—C9	1.435 (3)
O1—H1	0.8200	C9—C10	1.390 (3)
N1—C14	1.377 (3)	C9—C14	1.407 (3)
N1—C3	1.389 (3)	C10—C11	1.382 (3)
N1—C2	1.457 (3)	C10—H10A	0.9300
N2—C15	1.288 (3)	C11—C12	1.401 (3)
N2—C11	1.418 (3)	C12—C13	1.376 (3)
C1—C2	1.500 (4)	C12—H12A	0.9300
C1—H1A	0.9600	C13—C14	1.392 (3)
C1—H1B	0.9600	C13—H13A	0.9300
C1—H1C	0.9600	C15—C16	1.459 (4)
C2—H2B	0.9700	C15—H15A	0.9300
C2—H2C	0.9700	C16—C17	1.384 (4)
C3—C4	1.379 (3)	C16—C21	1.385 (4)
C3—C8	1.403 (3)	C17—C18	1.389 (4)
C4—C5	1.366 (4)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C19	1.376 (4)
C5—C6	1.380 (4)	C18—H18A	0.9300
C5—H5A	0.9300	C19—C20	1.378 (4)
C6—C7	1.371 (4)	C20—C21	1.377 (4)
C6—H6A	0.9300	C20—H20A	0.9300
C7—C8	1.390 (3)	C21—H21A	0.9300
C7—H7A	0.9300

C19—O1—H1	109.5	C14—C9—C8	106.9 (2)
C14—N1—C3	108.6 (2)	C11—C10—C9	120.0 (2)
C14—N1—C2	127.6 (2)	C11—C10—H10A	120.0
C3—N1—C2	123.7 (2)	C9—C10—H10A	120.0
C15—N2—C11	120.2 (2)	C10—C11—C12	119.8 (2)
C2—C1—H1A	109.5	C10—C11—N2	116.9 (2)
C2—C1—H1B	109.5	C12—C11—N2	123.3 (2)
H1A—C1—H1B	109.5	C13—C12—C11	121.5 (2)
C2—C1—H1C	109.5	C13—C12—H12A	119.2
H1A—C1—H1C	109.5	C11—C12—H12A	119.2
H1B—C1—H1C	109.5	C12—C13—C14	118.2 (2)
N1—C2—C1	111.7 (2)	C12—C13—H13A	120.9
N1—C2—H2B	109.3	C14—C13—H13A	120.9
C1—C2—H2B	109.3	N1—C14—C13	129.8 (2)
N1—C2—H2C	109.3	N1—C14—C9	108.9 (2)
C1—C2—H2C	109.3	C13—C14—C9	121.3 (2)
H2B—C2—H2C	107.9	N2—C15—C16	122.9 (3)
C4—C3—N1	129.4 (2)	N2—C15—H15A	118.5
C4—C3—C8	121.6 (3)	C16—C15—H15A	118.5
N1—C3—C8	109.0 (2)	C17—C16—C21	117.5 (3)
C5—C4—C3	118.0 (3)	C17—C16—C15	120.8 (3)
C5—C4—H4A	121.0	C21—C16—C15	121.6 (3)
C3—C4—H4A	121.0	C16—C17—C18	121.3 (3)
C4—C5—C6	121.4 (3)	C16—C17—H17A	119.4
C4—C5—H5A	119.3	C18—C17—H17A	119.4
C6—C5—H5A	119.3	C19—C18—C17	119.7 (3)
C7—C6—C5	121.1 (3)	C19—C18—H18A	120.2
C7—C6—H6A	119.5	C17—C18—H18A	120.2
C5—C6—H6A	119.5	O1—C19—C18	117.3 (3)
C6—C7—C8	118.9 (3)	O1—C19—C20	122.6 (3)
C6—C7—H7A	120.5	C18—C19—C20	120.0 (3)
C8—C7—H7A	120.5	C21—C20—C19	119.5 (3)
C7—C8—C3	119.0 (3)	C21—C20—H20A	120.2
C7—C8—C9	134.3 (2)	C19—C20—H20A	120.2
C3—C8—C9	106.6 (2)	C20—C21—C16	122.0 (3)
C10—C9—C14	119.2 (2)	C20—C21—H21A	119.0
C10—C9—C8	133.9 (2)	C16—C21—H21A	119.0

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.82	2.09	2.842 (3)	153
C1—H1A···Cg2ⁱⁱ	0.96	2.77	3.698 (2)	162

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₂O
M_r	314.37
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	13.386 (6), 9.247 (4), 26.443 (10)
V (Å³)	3273 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21605, 2878, 1615
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.140, 1.02
No. of reflections	2878
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.82	2.09	2.842 (3)	153
C1—H1A···Cg2ⁱⁱ	0.96	2.77	3.698 (2)	162

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

Acknowledgements

The authors would like to thank the Jilin Province Science and Technology Development Plan for support.

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
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