N-[(E)-4-Chloro­benzyl­idene]-2,3-dimethyl­aniline

Tahir, M.N.; Tariq, M.I.; Ahmad, S.; Sarfraz, M.; Ather, A.Q.

doi:10.1107/S1600536810020933

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1562

doi:10.1107/S1600536810020933

Open

access

N-[(E)-4-Chlorobenzylidene]-2,3-dimethylaniline

M. Nawaz Tahir,^a ^* Muhammad Ilyas Tariq,^b Shahbaz Ahmad,^b Muhammad Sarfraz ^b and Abdul Qayyum Ather ^c

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^cApplied Chemistry Research Center, PCSIR Laboratories complex, Lahore 54600, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 1 June 2010; accepted 1 June 2010; online 5 June 2010)

In the title compound, C₁₅H₁₄ClN, the conformation about the C=N bond is trans and the dihedral angle between the aromatic rings is 51.48 (4)°. In the crystal, some very weak C—H⋯π interactions may help to establish the packing.

Related literature

For a related structure and background to Schiff bases, see: Tariq et al. (2010 ). For related structures with different substituents at the N-bonded ring, see: Bürgi et al. (1968 ); Kazak et al. (2004 ); Ojala et al. (2001 ).

Experimental

Crystal data

C₁₅H₁₄ClN
M_r = 243.72
Monoclinic, P 2₁ /c
a = 12.8981 (4) Å
b = 7.7999 (2) Å
c = 15.0449 (5) Å
β = 119.315 (2)°
V = 1319.75 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.939, T_max = 0.950
10119 measured reflections
2378 independent reflections
1722 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.116
S = 1.05
2378 reflections
157 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg1ⁱ	0.93	2.99	3.649 (2)	129
C7—H7A⋯Cg2ⁱⁱ	0.96	2.93	3.757 (3)	145
C12—H12⋯Cg1ⁱⁱⁱ	0.93	2.96	3.793 (3)	150
C7—H7E⋯Cg2ⁱⁱ	0.96	3.00	3.757 (3)	137
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020933/hb5479sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020933/hb5479Isup2.hkl

checkCIF report

Comment top

In continuation to synthesize various Schiff bases (Tariq et al., 2010) of 2,3-dimethylaniline, the title compound (I, Fig. 1) is being reported.

The crystal structure of p-chlorobenzylideneaniline (Bürgi, et al., 1968), p-cyano-N-(p-chlorobenzylidene)aniline (Ojala et al., 2001) and 4-((4-Chlorobenzylidene)amino)phenol (Kazak et al., 2004) have been published which contain the chloro group at para position. The title compound differs from these due to substitutions at the aniline.

In (I), the 2,3-dimethylanilinic group A (C1—C8/N1) and the p-chlorobenzaldehyde B (C9—C15/CL1) are planar with maximum r. m. s. deviations of 0.0121 and 0.0071 Å, respectively. The dihedral angle between A/B is 51.48 (4)°. The molecules are essentially monomer with no appreciable intra-molecular H-bonding. The phenyl ring of 2,3-dimethylaniline has longer bond length [1.375 (3)–1.399 (2) Å] as compared to the phenyl ring of p-chlorobenzaldehyde [1.364 (4)–1.386 (3) Å]. The observed value of C═N bond is 1.264 (3) Å. All these bond lengths are compareable with 2,3-dimethyl-N-[(E)-(4-nitrophenyl)methylidene]aniline (Tariq et al., 2010). The molecules are stabilized due to C—H···π interactions (Table 1). The H-atoms of the methyl at ortho position are disordered over two set of sites with occupancy ratio 0.60 (3):0.40 (3).

Related literature top

For a related structure and background to Schiff bases, see: Tariq et al. (2010). For related structures with different substituents at the N-bonded ring, see: Bürgi et al. (1968); Kazak et al. (2004); Ojala et al. (2001).

Experimental top

Equimolar quantities of 2,3-dimethylaniline and 4-chlorobenzaldehyde were refluxed in methanol for 45 min resulting in yellow solution. The solution was kept at room temperature which affoarded colourless prisms of (I) after 48 h.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of (I) with displacement ellipsoids drawn at the 30% probability level.

N-[(E)-4-Chlorobenzylidene]-2,3-dimethylaniline top

Crystal data top

C₁₅H₁₄ClN	F(000) = 512
M_r = 243.72	D_x = 1.227 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1467 reflections
a = 12.8981 (4) Å	θ = 2.3–25.3°
b = 7.7999 (2) Å	µ = 0.27 mm⁻¹
c = 15.0449 (5) Å	T = 296 K
β = 119.315 (2)°	Prism, colourless
V = 1319.75 (7) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2378 independent reflections
Radiation source: fine-focus sealed tube	1722 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.7°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→9
T_min = 0.939, T_max = 0.950	l = −18→18
10119 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0502P)² + 0.2848P] where P = (F_o² + 2F_c²)/3
2378 reflections	(Δ/σ)_max < 0.001
157 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₄ClN	V = 1319.75 (7) Å³
M_r = 243.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8981 (4) Å	µ = 0.27 mm⁻¹
b = 7.7999 (2) Å	T = 296 K
c = 15.0449 (5) Å	0.30 × 0.20 × 0.20 mm
β = 119.315 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2378 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1722 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.950	R_int = 0.026
10119 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	Δρ_max = 0.15 e Å⁻³
2378 reflections	Δρ_min = −0.19 e Å⁻³
157 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
Cl1	0.03504 (6)	0.38426 (9)	−0.38533 (4)	0.1078 (3)
N1	0.47950 (12)	0.29383 (18)	0.09822 (10)	0.0549 (5)
C1	0.55065 (14)	0.2685 (2)	0.20499 (12)	0.0492 (5)
C2	0.66149 (14)	0.1905 (2)	0.24128 (12)	0.0502 (5)
C3	0.73394 (15)	0.1691 (2)	0.34649 (13)	0.0550 (6)
C4	0.69544 (17)	0.2286 (3)	0.41183 (14)	0.0673 (7)
C5	0.58704 (18)	0.3083 (3)	0.37546 (14)	0.0762 (8)
C6	0.51425 (17)	0.3277 (3)	0.27191 (14)	0.0654 (6)
C7	0.70003 (18)	0.1280 (3)	0.16739 (15)	0.0750 (8)
C8	0.85264 (17)	0.0805 (3)	0.39021 (15)	0.0821 (8)
C9	0.36888 (15)	0.2672 (2)	0.05682 (13)	0.0568 (6)
C10	0.28740 (15)	0.2988 (2)	−0.05166 (13)	0.0555 (6)
C11	0.32577 (17)	0.3762 (2)	−0.11338 (14)	0.0642 (7)
C12	0.24792 (19)	0.4016 (3)	−0.21581 (15)	0.0729 (7)
C13	0.13238 (18)	0.3509 (3)	−0.25623 (14)	0.0691 (7)
C14	0.09207 (17)	0.2742 (3)	−0.19726 (16)	0.0848 (9)
C15	0.16989 (16)	0.2490 (3)	−0.09440 (15)	0.0753 (8)
H4	0.74368	0.21437	0.48175	0.0807*
H5	0.56297	0.34907	0.42059	0.0914*
H6	0.44060	0.38061	0.24705	0.0784*
H7A	0.68581	0.00694	0.15699	0.1125*	0.60 (3)
H7B	0.78330	0.15045	0.19446	0.1125*	0.60 (3)
H7C	0.65559	0.18672	0.10356	0.1125*	0.60 (3)
H8A	0.88586	0.06855	0.46260	0.1231*
H8B	0.90540	0.14723	0.37604	0.1231*
H8C	0.84233	−0.03092	0.35984	0.1231*
H9	0.33782	0.22566	0.09688	0.0681*
H11	0.40448	0.41135	−0.08561	0.0771*
H12	0.27416	0.45295	−0.25702	0.0875*
H14	0.01323	0.23925	−0.22586	0.1018*
H15	0.14274	0.19794	−0.05375	0.0904*
H7D	0.63260	0.08266	0.10781	0.1125*	0.40 (3)
H7E	0.75885	0.03979	0.19898	0.1125*	0.40 (3)
H7F	0.73326	0.22166	0.14822	0.1125*	0.40 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1029 (5)	0.1121 (5)	0.0596 (4)	0.0316 (4)	0.0019 (3)	−0.0013 (3)
N1	0.0515 (8)	0.0532 (9)	0.0526 (8)	0.0013 (7)	0.0197 (7)	0.0026 (7)
C1	0.0506 (9)	0.0446 (9)	0.0496 (9)	−0.0022 (7)	0.0223 (8)	−0.0008 (7)
C2	0.0496 (9)	0.0472 (9)	0.0521 (9)	−0.0034 (7)	0.0237 (8)	−0.0011 (8)
C3	0.0507 (10)	0.0530 (10)	0.0547 (10)	−0.0025 (8)	0.0208 (8)	0.0002 (8)
C4	0.0662 (12)	0.0780 (14)	0.0478 (10)	−0.0004 (10)	0.0203 (9)	−0.0031 (10)
C5	0.0761 (14)	0.0942 (16)	0.0587 (12)	0.0091 (12)	0.0333 (10)	−0.0150 (11)
C6	0.0565 (10)	0.0693 (12)	0.0634 (11)	0.0110 (9)	0.0240 (9)	−0.0071 (10)
C7	0.0641 (12)	0.1002 (16)	0.0640 (12)	0.0125 (11)	0.0339 (10)	−0.0014 (11)
C8	0.0608 (12)	0.0989 (17)	0.0680 (12)	0.0163 (11)	0.0172 (10)	0.0052 (12)
C9	0.0553 (11)	0.0592 (11)	0.0562 (10)	−0.0001 (8)	0.0276 (9)	0.0001 (9)
C10	0.0517 (10)	0.0541 (10)	0.0549 (10)	0.0030 (8)	0.0215 (8)	−0.0039 (8)
C11	0.0590 (11)	0.0613 (12)	0.0598 (11)	−0.0094 (9)	0.0193 (9)	0.0031 (9)
C12	0.0848 (14)	0.0598 (12)	0.0607 (11)	−0.0062 (10)	0.0253 (11)	0.0057 (9)
C13	0.0657 (12)	0.0668 (13)	0.0553 (11)	0.0151 (10)	0.0145 (10)	−0.0052 (10)
C14	0.0459 (10)	0.122 (2)	0.0722 (14)	0.0036 (12)	0.0178 (10)	−0.0179 (14)
C15	0.0529 (11)	0.1084 (18)	0.0644 (12)	−0.0042 (11)	0.0285 (10)	−0.0059 (12)

Geometric parameters (Å, º) top

Cl1—C13	1.740 (2)	C4—H4	0.9300
N1—C1	1.421 (2)	C5—H5	0.9300
N1—C9	1.264 (3)	C6—H6	0.9300
C1—C2	1.396 (3)	C7—H7A	0.9600
C1—C6	1.382 (3)	C7—H7B	0.9600
C2—C3	1.399 (2)	C7—H7C	0.9600
C2—C7	1.504 (3)	C7—H7D	0.9600
C3—C4	1.381 (3)	C7—H7E	0.9600
C3—C8	1.506 (3)	C7—H7F	0.9600
C4—C5	1.375 (3)	C8—H8A	0.9600
C5—C6	1.378 (3)	C8—H8B	0.9600
C9—C10	1.466 (2)	C8—H8C	0.9600
C10—C11	1.386 (3)	C9—H9	0.9300
C10—C15	1.381 (3)	C11—H11	0.9300
C11—C12	1.381 (3)	C12—H12	0.9300
C12—C13	1.364 (4)	C14—H14	0.9300
C13—C14	1.366 (3)	C15—H15	0.9300
C14—C15	1.386 (3)

C1—N1—C9	118.88 (16)	C5—C6—H6	120.00
N1—C1—C2	118.29 (16)	C2—C7—H7A	109.00
N1—C1—C6	121.03 (17)	C2—C7—H7B	109.00
C2—C1—C6	120.59 (16)	C2—C7—H7C	109.00
C1—C2—C3	118.90 (17)	C2—C7—H7D	109.00
C1—C2—C7	119.88 (15)	C2—C7—H7E	109.00
C3—C2—C7	121.21 (18)	C2—C7—H7F	109.00
C2—C3—C4	119.44 (18)	H7A—C7—H7B	109.00
C2—C3—C8	121.46 (17)	H7A—C7—H7C	109.00
C4—C3—C8	119.10 (16)	H7B—C7—H7C	109.00
C3—C4—C5	121.24 (17)	H7D—C7—H7E	109.00
C4—C5—C6	119.8 (2)	H7D—C7—H7F	109.00
C1—C6—C5	120.0 (2)	H7E—C7—H7F	109.00
N1—C9—C10	122.83 (18)	C3—C8—H8A	109.00
C9—C10—C11	121.50 (19)	C3—C8—H8B	109.00
C9—C10—C15	119.75 (18)	C3—C8—H8C	109.00
C11—C10—C15	118.75 (17)	H8A—C8—H8B	109.00
C10—C11—C12	120.5 (2)	H8A—C8—H8C	109.00
C11—C12—C13	119.7 (2)	H8B—C8—H8C	109.00
Cl1—C13—C12	119.21 (17)	N1—C9—H9	119.00
Cl1—C13—C14	119.62 (18)	C10—C9—H9	119.00
C12—C13—C14	121.17 (19)	C10—C11—H11	120.00
C13—C14—C15	119.3 (2)	C12—C11—H11	120.00
C10—C15—C14	120.7 (2)	C11—C12—H12	120.00
C3—C4—H4	119.00	C13—C12—H12	120.00
C5—C4—H4	119.00	C13—C14—H14	120.00
C4—C5—H5	120.00	C15—C14—H14	120.00
C6—C5—H5	120.00	C10—C15—H15	120.00
C1—C6—H6	120.00	C14—C15—H15	120.00

C9—N1—C1—C2	139.41 (17)	C3—C4—C5—C6	0.9 (4)
C9—N1—C1—C6	−44.1 (2)	C4—C5—C6—C1	−0.6 (4)
C1—N1—C9—C10	176.57 (15)	N1—C9—C10—C11	−6.5 (3)
N1—C1—C2—C3	178.22 (15)	N1—C9—C10—C15	172.75 (18)
N1—C1—C2—C7	−3.0 (2)	C9—C10—C11—C12	178.72 (18)
C6—C1—C2—C3	1.7 (3)	C15—C10—C11—C12	−0.5 (3)
C6—C1—C2—C7	−179.55 (19)	C9—C10—C15—C14	−178.54 (19)
N1—C1—C6—C5	−177.17 (19)	C11—C10—C15—C14	0.7 (3)
C2—C1—C6—C5	−0.7 (3)	C10—C11—C12—C13	0.4 (3)
C1—C2—C3—C4	−1.4 (3)	C11—C12—C13—Cl1	179.79 (17)
C1—C2—C3—C8	177.88 (17)	C11—C12—C13—C14	−0.4 (4)
C7—C2—C3—C4	179.87 (19)	Cl1—C13—C14—C15	−179.61 (18)
C7—C2—C3—C8	−0.9 (3)	C12—C13—C14—C15	0.6 (4)
C2—C3—C4—C5	0.1 (3)	C13—C14—C15—C10	−0.7 (3)
C8—C3—C4—C5	−179.1 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1ⁱ	0.93	2.99	3.649 (2)	129
C7—H7A···Cg2ⁱⁱ	0.96	2.93	3.757 (3)	145
C12—H12···Cg1ⁱⁱⁱ	0.93	2.96	3.793 (3)	150
C7—H7E···Cg2ⁱⁱ	0.96	3.00	3.757 (3)	137

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClN
M_r	243.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.8981 (4), 7.7999 (2), 15.0449 (5)
β (°)	119.315 (2)
V (Å³)	1319.75 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.939, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	10119, 2378, 1722
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.116, 1.05
No. of reflections	2378
No. of parameters	157
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1ⁱ	0.93	2.99	3.649 (2)	129
C7—H7A···Cg2ⁱⁱ	0.96	2.93	3.757 (3)	145
C12—H12···Cg1ⁱⁱⁱ	0.93	2.96	3.793 (3)	150
C7—H7E···Cg2ⁱⁱ	0.96	3.00	3.757 (3)	137

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bürgi, H. B., Dunitz, J. D. & Züst, C. (1968). Acta Cryst. B24, 463–464. CSD CrossRef IUCr Journals Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kazak, C., Aygün, M., Turgut, G., Odabaşoğlu, M., Büyükgüngör, O. & Kahveci, N. (2004). Acta Cryst. E60, o252–o253. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ojala, C. R., Ojala, W. H., Gleason, W. B. & Britton, D. (2001). J. Chem. Crystallogr. 31, 377–386. Web of Science CSD CrossRef CAS 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
Tariq, M. I., Ahmad, S., Tahir, M. N., Sarfaraz, M. & Hussain, I. (2010). Acta Cryst. E66, o1561. 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 7| July 2010| Page o1562

doi:10.1107/S1600536810020933

Open

access