(E)-2-Chloro-N′-(2-hydr­oxy-1-naphthyl­methyl­ene)benzohydrazide

Qiu, F.; Zhao, L.-M.

doi:10.1107/S1600536808031371

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2067

doi:10.1107/S1600536808031371

Open

access

(E)-2-Chloro-N′-(2-hydroxy-1-naphthylmethylene)benzohydrazide

Feng Qiu ^a and Li-Mei Zhao ^a ^*

^aDepartment of Pharmacy, The Sheng Jing Hospital of Chinese Medical University, Shenyang 110004, People's Republic of China
^*Correspondence e-mail: zhaolm08@126.com

(Received 26 September 2008; accepted 28 September 2008; online 4 October 2008)

In the structue of the title compound, C₁₈H₁₃ClN₂O₂, a new Schiff base, the dihedral angle between the benzene and naphthyl ring system mean planes is 22.5 (2)°. The molecule has an E configuration about the C=N bond, and an intramolecular hydrogen bond involving the hydoxyl substituent on the naphthyl ring and the N′ atom of the hydrazide. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, forming one-dimensional chains running parallel to the a axis.

Related literature

For background on Schiff base compounds, hydrazone compounds and their biological properties, see: Kucukguzel et al. (2006 ); Khattab (2005 ); Karthikeyan et al. (2006 ); Okabe et al. (1993 ). For bond distances, see: Allen et al. (1987 ). For related structures, see: Shan et al. (2008 ); Fun et al. (2008 ); Yang (2008 ); Ma et al. (2008 ); Diao, Huang et al. (2008 ); Diao, Zhen et al. (2008 ); Ejsmont et al. (2008 ).

Experimental

Crystal data

C₁₈H₁₃ClN₂O₂
M_r = 324.75
Monoclinic, P 2₁ /n
a = 7.2797 (14) Å
b = 29.148 (6) Å
c = 7.6889 (16) Å
β = 112.130 (3)°
V = 1511.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 (2) K
0.32 × 0.27 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.920, T_max = 0.934
8693 measured reflections
3255 independent reflections
2320 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.105
S = 1.03
3255 reflections
213 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.896 (9)	1.972 (11)	2.842 (2)	163.5 (18)
O1—H1⋯N1	0.82	1.86	2.581 (2)	146
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031371/su2067sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031371/su2067Isup2.hkl

checkCIF report

Comment top

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab, 2005; Karthikeyan et al., 2006; Okabe et al., 1993). Recently, a large number of hydrazone derivatives have been prepared and structurally characterized (Shan et al., 2008; Fun et al., 2008; Yang, 2008; Ma et al., 2008; Diao, Huang et al., 2008; Diao, Zhen et al., 2008; Ejsmont et al., 2008). As part of an ongoing study, we report herein the crystal structure of the title compound, (I).

The molecular structure of compound (I) is shown in Fig. 1. The bond dstances and angles are normal (Allen et al., 1987). The dihedral angle between the phenyl and naphthyl ring mean planes is 22.5 (2)°. The compound displays an E configuration about the C═N bond, and an intramolecular hydrogen bond involving the hydoxyl substituent on the naphthyl ring and the N-atom of the hydrazide (Table 1). The crystal structure is stabilized by intermolecular N—H···O hydrogen bonds (Table 1), forming one-dimensional chains running parallel to the a axis, Fig. 2.

Related literature top

For background on Schiff base compounds, hydrazone compounds and their biological properties, see: Kucukguzel et al. (2006); Khattab (2005); Karthikeyan et al. (2006); Okabe et al. (1993). For bond distances, see: Allen et al. (1987). For related structures, see: Shan et al. (2008); Fun et al. (2008); Yang (2008); Ma et al. (2008); Diao, Huang et al. (2008); Diao, Zhen et al. (2008); Ejsmont et al. (2008).

Experimental top

Compound (I) was prepared by dissolving 2-Hydroxy-1-naphthaldehyde (1.0 mmol, 172.3 mg) in methanol (50 ml), then 2-chlorobenzohydrazide (1.0 mmol, 170.2 mg) was added slowly and the mixture kept at reflux with continuous stirring for 3 h. When the solution was cooled to room temperature a colourless crystalline powder appeared. This was filtered off and washed with methanol three times. Recrystallization from absolute methanol yielded block-shaped single crystals suitable for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. The molecular structure of compound (I) with 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Crystal packing of compound (I) viewed along the c axis (Hydrogen bonds are shown as dashed lines).

(E)-2-Chloro-N'-(2-hydroxy-1-naphthylmethylene)benzohydrazide top

Crystal data top

C₁₈H₁₃ClN₂O₂	F(000) = 672
M_r = 324.75	D_x = 1.427 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.2797 (14) Å	Cell parameters from 2129 reflections
b = 29.148 (6) Å	θ = 2.5–25.3°
c = 7.6889 (16) Å	µ = 0.26 mm⁻¹
β = 112.130 (3)°	T = 298 K
V = 1511.3 (5) Å³	Block, colourless
Z = 4	0.32 × 0.27 × 0.26 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3255 independent reflections
Radiation source: fine-focus sealed tube	2320 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 27.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.920, T_max = 0.935	k = −31→37
8693 measured reflections	l = −9→6

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0421P)² + 0.2242P] where P = (F_o² + 2F_c²)/3
3255 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₃ClN₂O₂	V = 1511.3 (5) Å³
M_r = 324.75	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2797 (14) Å	µ = 0.26 mm⁻¹
b = 29.148 (6) Å	T = 298 K
c = 7.6889 (16) Å	0.32 × 0.27 × 0.26 mm
β = 112.130 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3255 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2320 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.935	R_int = 0.036
8693 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.21 e Å⁻³
3255 reflections	Δρ_min = −0.20 e Å⁻³
213 parameters

Special details top

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
Cl1	0.90066 (8)	0.109541 (17)	0.58158 (8)	0.05120 (18)
N1	0.9283 (2)	0.28478 (5)	0.6687 (2)	0.0368 (4)
N2	0.8931 (2)	0.25535 (5)	0.5185 (2)	0.0368 (4)
O1	0.9748 (2)	0.30053 (5)	1.0131 (2)	0.0538 (4)
H1	0.9791	0.2855	0.9244	0.081*
O2	1.10008 (19)	0.20185 (4)	0.70363 (18)	0.0444 (4)
C1	0.8785 (2)	0.35871 (6)	0.7742 (3)	0.0344 (4)
C2	0.9227 (3)	0.34426 (6)	0.9575 (3)	0.0393 (5)
C3	0.9128 (3)	0.37438 (7)	1.0959 (3)	0.0474 (5)
H3	0.9382	0.3637	1.2167	0.057*
C4	0.8661 (3)	0.41905 (8)	1.0537 (3)	0.0513 (6)
H4	0.8594	0.4386	1.1467	0.062*
C5	0.8273 (3)	0.43664 (7)	0.8724 (3)	0.0451 (5)
C6	0.7811 (4)	0.48343 (8)	0.8286 (4)	0.0652 (7)
H6	0.7739	0.5032	0.9210	0.078*
C7	0.7473 (4)	0.49996 (8)	0.6555 (5)	0.0782 (9)
H7	0.7179	0.5309	0.6294	0.094*
C8	0.7564 (4)	0.47067 (8)	0.5156 (4)	0.0739 (8)
H8	0.7334	0.4823	0.3966	0.089*
C9	0.7988 (3)	0.42509 (7)	0.5512 (3)	0.0542 (6)
H9	0.8043	0.4061	0.4561	0.065*
C10	0.8341 (3)	0.40654 (6)	0.7300 (3)	0.0388 (5)
C11	0.8664 (3)	0.32609 (6)	0.6287 (3)	0.0355 (4)
H11	0.8127	0.3352	0.5037	0.043*
C12	0.9814 (3)	0.21388 (6)	0.5489 (3)	0.0329 (4)
C13	0.9258 (2)	0.18457 (6)	0.3775 (3)	0.0317 (4)
C14	0.8905 (3)	0.13760 (6)	0.3788 (3)	0.0348 (4)
C15	0.8421 (3)	0.11196 (7)	0.2176 (3)	0.0471 (5)
H15	0.8181	0.0807	0.2204	0.057*
C16	0.8291 (3)	0.13237 (8)	0.0521 (3)	0.0529 (6)
H16	0.7964	0.1148	−0.0565	0.064*
C17	0.8642 (3)	0.17866 (7)	0.0464 (3)	0.0501 (5)
H17	0.8559	0.1924	−0.0654	0.060*
C18	0.9117 (3)	0.20441 (6)	0.2079 (3)	0.0396 (5)
H18	0.9349	0.2357	0.2037	0.048*
H2	0.799 (2)	0.2634 (6)	0.4086 (18)	0.047 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0587 (3)	0.0436 (3)	0.0540 (4)	−0.0002 (2)	0.0242 (3)	0.0116 (2)
N1	0.0399 (9)	0.0341 (8)	0.0326 (9)	0.0012 (7)	0.0095 (7)	−0.0065 (7)
N2	0.0402 (9)	0.0344 (8)	0.0278 (9)	0.0059 (7)	0.0039 (7)	−0.0035 (7)
O1	0.0788 (11)	0.0439 (8)	0.0389 (9)	0.0039 (8)	0.0224 (8)	0.0056 (7)
O2	0.0500 (8)	0.0404 (7)	0.0294 (8)	0.0053 (6)	−0.0006 (6)	0.0002 (6)
C1	0.0308 (9)	0.0349 (10)	0.0356 (11)	−0.0021 (8)	0.0105 (8)	−0.0039 (8)
C2	0.0366 (10)	0.0419 (11)	0.0401 (12)	−0.0046 (9)	0.0154 (9)	−0.0041 (9)
C3	0.0508 (12)	0.0563 (13)	0.0383 (12)	−0.0091 (10)	0.0205 (10)	−0.0107 (10)
C4	0.0491 (12)	0.0551 (13)	0.0530 (15)	−0.0102 (10)	0.0228 (11)	−0.0247 (11)
C5	0.0374 (11)	0.0402 (11)	0.0547 (14)	−0.0054 (9)	0.0141 (10)	−0.0149 (10)
C6	0.0664 (16)	0.0421 (13)	0.079 (2)	0.0021 (11)	0.0187 (14)	−0.0185 (13)
C7	0.092 (2)	0.0353 (13)	0.094 (2)	0.0088 (12)	0.0198 (18)	0.0016 (14)
C8	0.096 (2)	0.0482 (14)	0.0684 (19)	0.0107 (13)	0.0212 (15)	0.0119 (13)
C9	0.0691 (15)	0.0403 (12)	0.0506 (14)	0.0050 (10)	0.0196 (12)	0.0016 (10)
C10	0.0328 (10)	0.0354 (10)	0.0457 (12)	−0.0023 (8)	0.0120 (9)	−0.0045 (9)
C11	0.0353 (10)	0.0362 (10)	0.0318 (10)	−0.0013 (8)	0.0089 (8)	−0.0015 (8)
C12	0.0338 (10)	0.0324 (9)	0.0301 (10)	−0.0017 (8)	0.0093 (8)	0.0010 (8)
C13	0.0293 (9)	0.0341 (9)	0.0285 (10)	0.0028 (8)	0.0074 (8)	−0.0017 (8)
C14	0.0318 (9)	0.0339 (10)	0.0361 (11)	0.0023 (8)	0.0097 (8)	0.0005 (8)
C15	0.0470 (12)	0.0372 (11)	0.0528 (14)	−0.0003 (9)	0.0139 (10)	−0.0097 (10)
C16	0.0553 (13)	0.0575 (14)	0.0384 (13)	0.0062 (11)	0.0091 (10)	−0.0156 (11)
C17	0.0575 (13)	0.0597 (14)	0.0326 (12)	0.0077 (11)	0.0163 (10)	0.0002 (10)
C18	0.0434 (11)	0.0378 (10)	0.0355 (11)	0.0037 (9)	0.0124 (9)	0.0013 (9)

Geometric parameters (Å, º) top

Cl1—C14	1.737 (2)	C6—H6	0.9300
N1—C11	1.282 (2)	C7—C8	1.394 (4)
N1—N2	1.383 (2)	C7—H7	0.9300
N2—C12	1.347 (2)	C8—C9	1.368 (3)
N2—H2	0.896 (9)	C8—H8	0.9300
O1—C2	1.353 (2)	C9—C10	1.408 (3)
O1—H1	0.8200	C9—H9	0.9300
O2—C12	1.229 (2)	C11—H11	0.9300
C1—C2	1.388 (3)	C12—C13	1.493 (2)
C1—C10	1.443 (3)	C13—C14	1.394 (2)
C1—C11	1.445 (3)	C13—C18	1.395 (3)
C2—C3	1.402 (3)	C14—C15	1.375 (3)
C3—C4	1.354 (3)	C15—C16	1.375 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.411 (3)	C16—C17	1.377 (3)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.415 (3)	C17—C18	1.379 (3)
C5—C10	1.418 (3)	C17—H17	0.9300
C6—C7	1.348 (4)	C18—H18	0.9300

C11—N1—N2	116.37 (16)	C8—C9—H9	119.6
C12—N2—N1	119.02 (15)	C10—C9—H9	119.6
C12—N2—H2	123.0 (13)	C9—C10—C5	118.02 (18)
N1—N2—H2	117.4 (13)	C9—C10—C1	122.90 (18)
C2—O1—H1	109.5	C5—C10—C1	119.08 (19)
C2—C1—C10	118.55 (17)	N1—C11—C1	121.25 (18)
C2—C1—C11	120.65 (17)	N1—C11—H11	119.4
C10—C1—C11	120.71 (17)	C1—C11—H11	119.4
O1—C2—C1	122.49 (17)	O2—C12—N2	122.65 (17)
O1—C2—C3	116.01 (18)	O2—C12—C13	123.31 (16)
C1—C2—C3	121.50 (19)	N2—C12—C13	114.02 (15)
C4—C3—C2	120.0 (2)	C14—C13—C18	117.70 (17)
C4—C3—H3	120.0	C14—C13—C12	123.07 (17)
C2—C3—H3	120.0	C18—C13—C12	119.22 (16)
C3—C4—C5	121.66 (19)	C15—C14—C13	120.87 (19)
C3—C4—H4	119.2	C15—C14—Cl1	117.58 (15)
C5—C4—H4	119.2	C13—C14—Cl1	121.53 (14)
C4—C5—C6	121.8 (2)	C16—C15—C14	120.25 (19)
C4—C5—C10	119.08 (19)	C16—C15—H15	119.9
C6—C5—C10	119.1 (2)	C14—C15—H15	119.9
C7—C6—C5	121.2 (2)	C15—C16—C17	120.3 (2)
C7—C6—H6	119.4	C15—C16—H16	119.8
C5—C6—H6	119.4	C17—C16—H16	119.8
C6—C7—C8	119.9 (2)	C16—C17—C18	119.4 (2)
C6—C7—H7	120.0	C16—C17—H17	120.3
C8—C7—H7	120.0	C18—C17—H17	120.3
C9—C8—C7	120.9 (3)	C17—C18—C13	121.45 (18)
C9—C8—H8	119.6	C17—C18—H18	119.3
C7—C8—H8	119.6	C13—C18—H18	119.3
C8—C9—C10	120.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (1)	1.97 (1)	2.842 (2)	164 (2)
O1—H1···N1	0.82	1.86	2.581 (2)	146

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃ClN₂O₂
M_r	324.75
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.2797 (14), 29.148 (6), 7.6889 (16)
β (°)	112.130 (3)
V (Å³)	1511.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.32 × 0.27 × 0.26

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.920, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	8693, 3255, 2320
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.105, 1.04
No. of reflections	3255
No. of parameters	213
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.896 (9)	1.972 (11)	2.842 (2)	163.5 (18)
O1—H1···N1	0.82	1.86	2.581 (2)	146.2

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Diao, Y.-P., Huang, S.-S., Zhang, J.-K. & Kang, T.-G. (2008). Acta Cryst. E64, o470. Web of Science CSD CrossRef IUCr Journals Google Scholar
Diao, Y.-P., Zhen, Y.-H., Han, X. & Deng, S. (2008). Acta Cryst. E64, o101. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Sujith, K. V., Patil, P. S., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1961–o1962. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482–7489. Web of Science CrossRef PubMed CAS Google Scholar
Khattab, S. N. (2005). Molecules 10, 1218–1228. Web of Science CrossRef PubMed CAS Google Scholar
Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahi, F. & Gulluce, M. (2006). Eur. J. Med. Chem. 41, 353–359. Web of Science CrossRef PubMed Google Scholar
Ma, H.-B., Huang, S.-S. & Diao, Y.-P. (2008). Acta Cryst. E64, o210. Web of Science CSD CrossRef IUCr Journals Google Scholar
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Shan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008). Acta Cryst. E64, o1363. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, D.-S. (2008). Acta Cryst. E64, o1759. Web of Science 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 64| Part 11| November 2008| Page o2067

doi:10.1107/S1600536808031371

Open

access