Methyl 2-meth­oxy-4-{[2-(4-nitro­phen­yl)hydrazinyl­idene]meth­yl}benzoate

Zhao, Z.; Li, H.; Ma, B.

doi:10.1107/S160053681003802X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2661

doi:10.1107/S160053681003802X

Open

access

Methyl 2-methoxy-4-{[2-(4-nitrophenyl)hydrazinylidene]methyl}benzoate

Zhen-xin Zhao,^a ^* He-ping Li ^b and Bu-wei Ma ^c

^aDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan 467044, People's Republic of China, ^bSchool of Chemistry and Biological Engineering, Guilin University of Technology, People's Republic of China, and ^cDepartment of Architectural Environment, and Energy Engineering, Henan University of Urban Construction, Pingdingshan 467044, People's Republic of China
^*Correspondence e-mail: zhao_zhenxin@126.com

(Received 19 September 2010; accepted 23 September 2010; online 30 September 2010)

The molecule of the title Schiff base compound, C₁₆H₁₅N₃O₅, obtained from a condensation reaction of 4-acetoxy-3-methoxybenzaldehyde and 4-nitrophenylhydrazine, adopts an E geometry with respect to the C=N double bond. The molecule is roughly planar, with the two benzene rings twisted slightly with respect to each other by a dihedral angle of 6.90 (9)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link centrosymmetrically related pairs of molecules, forming dimers of R₂²(22) graph-set motif. The dimers are further connected through slipped π–π interactions between symmetry-related benzene rings [centroid–centroid distance of 3.646 (1) Å, offset angle of 15.4°].

Related literature

For potential applications of hydrazone derivatives, see: Okabe et al. (1993 ). For related structures, see: Szczesna & Urbanczyk-Lipkowska (2002 ); Zhen & Han (2005 ); Kuleshova et al. (2003 ); Baughman et al. (2004 ). For hydrogen-bond motifs, see: Etter et al. (1990 ); Bernstein et al. (1994 ).

Experimental

Crystal data

C₁₆H₁₅N₃O₅
M_r = 329.31
Monoclinic, P 2₁ /c
a = 8.5983 (7) Å
b = 14.6982 (9) Å
c = 13.2096 (10) Å
β = 107.860 (9)°
V = 1589.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.23 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.971, T_max = 0.976
6773 measured reflections
3255 independent reflections
1397 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.072
S = 0.72
3255 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.86	2.29	3.0068 (19)	141
Symmetry code: (i) -x+2, -y, -z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003802X/dn2604sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681003802X/dn2604Isup2.hkl

checkCIF report

Comment top

As some phenylhydrazone derivatives show potential application in biochemistry(Okabe et al.,1993), phenylhydrazone has recently attracted our attention. In this paper, we report the synthesis and crystal structure of the title compound.

The molecule adopts an E geometry with respect to the C=N double bond (Fig. 1). The methoxybenzene and the nitrobenzene rings are roughly planar, with however the two benzene rings slightly twisted with respect to each other by a dihedral angle of 6.90 (9)°. The geometry within the hydrazone moiety agrees with related compound found in the literature (Szczesna & Urbanczyk-Lipkowska, 2002; Zhen & Han, 2005; Kuleshova et al., 2003; Baughman et al., 2004.

Intermolecular N—H···O hydrogen bonds link the molecule two by two to form dimer (Table 1, Fig. 2) with R²₂(22) graph set motif (Etter et al., 1990); Bernstein et al., 1994). The dimers are connected through slippest π-π interactions involving the symmetry related (1-x, -y, -z) C1-C6 and C8-C13 benzene rings with a centroid to centroid distance of 3.646 (1)Å and an interplanar distance of 3.515Å resulting in an offset angle of 15.4°.

Related literature top

For potential applications of hydrazone derivatives, see: Okabe et al. (1993). For related structures, see: Szczesna & Urbanczyk-Lipkowska (2002); Zhen & Han (2005); Kuleshova et al. (2003); Baughman et al. (2004). For hydrogen-bond motifs, see: Etter et al. (1990); Bernstein et al. (1994).

Experimental top

4-Nitrophenylhydrazine (1 mmol, 0.153 g) was dissolved in anhydrous ethanol (10 ml), The mixture was stirred for several minitutes at 351k, 4-acetoxy-3-methoxybenzaldehyde(1 mmol, 0.194 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol/dicholomethane(1:1), red single crystals of (I) was obtained after 3 d.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of the title compound with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the formation of dimer through N-H···O hydrogen bonds shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) -x+2, -y, -z]

Methyl 2-methoxy-4-{[2-(4-nitrophenyl)hydrazinylidene]methyl}benzoate top

Crystal data top

C₁₆H₁₅N₃O₅	F(000) = 688
M_r = 329.31	D_x = 1.377 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1694 reflections
a = 8.5983 (7) Å	θ = 3.2–26.3°
b = 14.6982 (9) Å	µ = 0.10 mm⁻¹
c = 13.2096 (10) Å	T = 293 K
β = 107.860 (9)°	Block, red
V = 1589.0 (2) Å³	0.23 × 0.20 × 0.19 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3255 independent reflections
Radiation source: fine-focus sealed tube	1397 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 26.4°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
T_min = 0.971, T_max = 0.976	k = −15→18
6773 measured reflections	l = −16→10

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 0.72	w = 1/[σ²(F_o²) + (0.032P)²] where P = (F_o² + 2F_c²)/3
3255 reflections	(Δ/σ)_max = 0.007
219 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₆H₁₅N₃O₅	V = 1589.0 (2) Å³
M_r = 329.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5983 (7) Å	µ = 0.10 mm⁻¹
b = 14.6982 (9) Å	T = 293 K
c = 13.2096 (10) Å	0.23 × 0.20 × 0.19 mm
β = 107.860 (9)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3255 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1397 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.976	R_int = 0.029
6773 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 0.72	Δρ_max = 0.13 e Å⁻³
3255 reflections	Δρ_min = −0.16 e Å⁻³
219 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 > 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	0.3583 (2)	0.28271 (10)	0.40773 (12)	0.0934 (5)
O2	0.41338 (19)	0.17034 (10)	0.51701 (12)	0.0912 (5)
O3	0.94760 (16)	−0.07061 (8)	−0.28742 (9)	0.0600 (4)
O4	0.84502 (16)	0.09303 (8)	−0.37261 (9)	0.0560 (4)
O5	1.10849 (17)	0.12748 (8)	−0.29655 (11)	0.0628 (4)
N1	0.66329 (16)	0.00919 (9)	0.15774 (11)	0.0493 (4)
H1	0.6925	−0.0461	0.1750	0.059*
N2	0.68044 (17)	0.04452 (9)	0.06596 (11)	0.0451 (4)
N3	0.4121 (2)	0.20643 (13)	0.43252 (14)	0.0649 (5)
C1	0.6057 (2)	0.02353 (12)	0.32125 (14)	0.0522 (5)
H1B	0.6504	−0.0339	0.3408	0.063*
C2	0.5452 (2)	0.07193 (13)	0.38904 (14)	0.0553 (5)
H2B	0.5495	0.0478	0.4549	0.066*
C3	0.4777 (2)	0.15662 (12)	0.35965 (15)	0.0468 (5)
C4	0.4691 (2)	0.19305 (11)	0.26147 (14)	0.0495 (5)
H4A	0.4215	0.2498	0.2416	0.059*
C5	0.5311 (2)	0.14503 (11)	0.19376 (14)	0.0468 (5)
H5A	0.5266	0.1696	0.1280	0.056*
C6	0.6006 (2)	0.06010 (12)	0.22253 (14)	0.0417 (4)
C7	0.7483 (2)	−0.00733 (11)	0.01437 (13)	0.0452 (5)
H7A	0.7806	−0.0654	0.0403	0.054*
C8	0.7767 (2)	0.02182 (11)	−0.08375 (13)	0.0403 (4)
C9	0.85046 (19)	−0.03850 (11)	−0.13560 (13)	0.0434 (5)
H9A	0.8822	−0.0956	−0.1061	0.052*
C10	0.8777 (2)	−0.01552 (11)	−0.23029 (14)	0.0434 (5)
C11	0.8294 (2)	0.06963 (12)	−0.27239 (13)	0.0449 (5)
C12	0.7565 (2)	0.13013 (11)	−0.22286 (15)	0.0518 (5)
H12A	0.7246	0.1870	−0.2528	0.062*
C13	0.7300 (2)	0.10665 (11)	−0.12796 (15)	0.0516 (5)
H13A	0.6809	0.1479	−0.0939	0.062*
C14	0.9936 (2)	−0.15954 (11)	−0.24715 (14)	0.0632 (6)
H14A	1.0419	−0.1913	−0.2935	0.095*
H14B	0.8987	−0.1920	−0.2433	0.095*
H14C	1.0714	−0.1554	−0.1774	0.095*
C15	0.9935 (3)	0.12176 (12)	−0.37443 (17)	0.0507 (5)
C16	0.9907 (3)	0.14511 (15)	−0.48491 (15)	0.0823 (7)
H16A	0.9030	0.1868	−0.5155	0.123*
H16B	0.9748	0.0907	−0.5271	0.123*
H16C	1.0927	0.1728	−0.4832	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1226 (15)	0.0764 (11)	0.0863 (11)	0.0205 (11)	0.0397 (10)	−0.0154 (10)
O2	0.1189 (14)	0.1058 (12)	0.0648 (10)	−0.0012 (10)	0.0517 (10)	−0.0052 (9)
O3	0.0790 (10)	0.0505 (7)	0.0600 (9)	0.0083 (7)	0.0352 (8)	0.0004 (7)
O4	0.0524 (9)	0.0728 (9)	0.0439 (8)	−0.0030 (8)	0.0165 (7)	0.0089 (7)
O5	0.0551 (9)	0.0710 (9)	0.0609 (9)	−0.0025 (8)	0.0159 (8)	0.0054 (8)
N1	0.0584 (11)	0.0466 (9)	0.0481 (10)	0.0032 (8)	0.0239 (9)	0.0052 (8)
N2	0.0454 (10)	0.0511 (9)	0.0398 (9)	−0.0051 (8)	0.0144 (8)	0.0022 (8)
N3	0.0633 (13)	0.0740 (13)	0.0596 (13)	−0.0106 (11)	0.0220 (11)	−0.0172 (11)
C1	0.0561 (14)	0.0545 (11)	0.0498 (12)	0.0049 (10)	0.0219 (11)	0.0108 (10)
C2	0.0574 (14)	0.0680 (13)	0.0445 (12)	−0.0063 (11)	0.0214 (11)	0.0074 (11)
C3	0.0452 (13)	0.0533 (12)	0.0450 (12)	−0.0092 (10)	0.0186 (10)	−0.0085 (10)
C4	0.0509 (14)	0.0436 (11)	0.0530 (12)	−0.0085 (10)	0.0145 (11)	−0.0036 (10)
C5	0.0546 (13)	0.0444 (11)	0.0428 (11)	−0.0092 (10)	0.0172 (10)	0.0019 (9)
C6	0.0398 (11)	0.0472 (11)	0.0379 (11)	−0.0100 (9)	0.0117 (9)	−0.0017 (9)
C7	0.0427 (13)	0.0459 (11)	0.0464 (12)	−0.0054 (10)	0.0131 (10)	−0.0006 (9)
C8	0.0397 (12)	0.0405 (10)	0.0408 (11)	−0.0068 (9)	0.0124 (10)	−0.0009 (9)
C9	0.0434 (13)	0.0392 (10)	0.0472 (12)	−0.0011 (9)	0.0131 (10)	−0.0007 (9)
C10	0.0409 (12)	0.0441 (11)	0.0458 (12)	−0.0023 (10)	0.0144 (10)	−0.0066 (10)
C11	0.0417 (12)	0.0540 (12)	0.0386 (11)	−0.0017 (10)	0.0117 (10)	0.0044 (10)
C12	0.0548 (13)	0.0447 (11)	0.0599 (13)	0.0036 (10)	0.0238 (11)	0.0082 (10)
C13	0.0561 (13)	0.0457 (11)	0.0592 (13)	0.0017 (10)	0.0268 (11)	−0.0035 (10)
C14	0.0789 (16)	0.0483 (11)	0.0683 (14)	0.0097 (11)	0.0316 (13)	−0.0045 (11)
C15	0.0583 (14)	0.0454 (11)	0.0525 (13)	0.0064 (11)	0.0232 (12)	0.0019 (10)
C16	0.0886 (18)	0.1103 (17)	0.0573 (14)	−0.0082 (15)	0.0361 (13)	0.0100 (13)

Geometric parameters (Å, º) top

O1—N3	1.2188 (18)	C5—C6	1.386 (2)
O2—N3	1.2326 (18)	C5—H5A	0.9300
O3—C10	1.3655 (18)	C7—C8	1.455 (2)
O3—C14	1.4210 (18)	C7—H7A	0.9300
O4—C15	1.352 (2)	C8—C13	1.383 (2)
O4—C11	1.4135 (18)	C8—C9	1.387 (2)
O5—C15	1.191 (2)	C9—C10	1.383 (2)
N1—C6	1.3663 (18)	C9—H9A	0.9300
N1—N2	1.3678 (16)	C10—C11	1.381 (2)
N1—H1	0.8600	C11—C12	1.365 (2)
N2—C7	1.2766 (18)	C12—C13	1.385 (2)
N3—C3	1.454 (2)	C12—H12A	0.9300
C1—C2	1.366 (2)	C13—H13A	0.9300
C1—C6	1.399 (2)	C14—H14A	0.9600
C1—H1B	0.9300	C14—H14B	0.9600
C2—C3	1.378 (2)	C14—H14C	0.9600
C2—H2B	0.9300	C15—C16	1.492 (2)
C3—C4	1.384 (2)	C16—H16A	0.9600
C4—C5	1.369 (2)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600

C10—O3—C14	117.25 (13)	C9—C8—C7	118.60 (16)
C15—O4—C11	117.01 (14)	C10—C9—C8	121.35 (16)
C6—N1—N2	121.19 (14)	C10—C9—H9A	119.3
C6—N1—H1	119.4	C8—C9—H9A	119.3
N2—N1—H1	119.4	O3—C10—C11	116.35 (16)
C7—N2—N1	115.96 (14)	O3—C10—C9	125.47 (16)
O1—N3—O2	122.44 (18)	C11—C10—C9	118.18 (16)
O1—N3—C3	118.54 (18)	C12—C11—C10	121.53 (17)
O2—N3—C3	119.02 (19)	C12—C11—O4	118.68 (16)
C2—C1—C6	120.11 (17)	C10—C11—O4	119.64 (16)
C2—C1—H1B	119.9	C11—C12—C13	119.91 (16)
C6—C1—H1B	119.9	C11—C12—H12A	120.0
C1—C2—C3	119.87 (17)	C13—C12—H12A	120.0
C1—C2—H2B	120.1	C8—C13—C12	120.00 (16)
C3—C2—H2B	120.1	C8—C13—H13A	120.0
C2—C3—C4	120.70 (17)	C12—C13—H13A	120.0
C2—C3—N3	118.93 (18)	O3—C14—H14A	109.5
C4—C3—N3	120.36 (18)	O3—C14—H14B	109.5
C5—C4—C3	119.54 (17)	H14A—C14—H14B	109.5
C5—C4—H4A	120.2	O3—C14—H14C	109.5
C3—C4—H4A	120.2	H14A—C14—H14C	109.5
C4—C5—C6	120.43 (16)	H14B—C14—H14C	109.5
C4—C5—H5A	119.8	O5—C15—O4	123.01 (18)
C6—C5—H5A	119.8	O5—C15—C16	126.1 (2)
N1—C6—C5	122.77 (16)	O4—C15—C16	110.93 (19)
N1—C6—C1	117.89 (16)	C15—C16—H16A	109.5
C5—C6—C1	119.33 (17)	C15—C16—H16B	109.5
N2—C7—C8	121.93 (16)	H16A—C16—H16B	109.5
N2—C7—H7A	119.0	C15—C16—H16C	109.5
C8—C7—H7A	119.0	H16A—C16—H16C	109.5
C13—C8—C9	119.02 (16)	H16B—C16—H16C	109.5
C13—C8—C7	122.37 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.86	2.29	3.0068 (19)	141

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₃O₅
M_r	329.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.5983 (7), 14.6982 (9), 13.2096 (10)
β (°)	107.860 (9)
V (Å³)	1589.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.971, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	6773, 3255, 1397
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.072, 0.72
No. of reflections	3255
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.16

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.86	2.29	3.0068 (19)	140.7

Symmetry code: (i) −x+2, −y, −z.

References

Baughman, R. G., Martin, K. L., Singh, R. K. & Stoffer, J. O. (2004). Acta Cryst. C60, o103–o106. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Etter, M. C. & Leiserowitz, L. (1994). Structure Correlation, Vol. 2, edited by H.-B. Bürgi & J. D. Dunitz, pp. 431–507. New York: VCH. Google Scholar
Bruker (1998). SMART (Version 5.628), SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kuleshova, L. N., Antipin, M. Yu., Khrustalev, V. N., Gusev, D. V., Grintselev-Knyazev, G. V. & Bobrikova, E. S. (2003). Crystallogr. Rep. 48, 594–601. Web of Science CrossRef CAS Google Scholar
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szczesna, B. & Urbanczyk-Lipkowska, Z. (2002). New J. Chem. 26, 243–249 Web of Science CSD CrossRef CAS Google Scholar
Zhen, X.-L. & Han, J.-R. (2005). Acta Cryst. E61, o3721–o3722. 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 66| Part 10| October 2010| Page o2661

doi:10.1107/S160053681003802X

Open

access