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

Fun, H.-K.; Quah, C.K.; Viveka, S.; Madhukumar, D.J.; Prasad, D.J.

doi:10.1107/S1600536811026109

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1932

doi:10.1107/S1600536811026109

Open

access

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

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § S. Viveka,^b D. J. Madhukumar ^b and D. Jagadeesh Prasad ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 28 June 2011; accepted 1 July 2011; online 6 July 2011)

The title molecule, C₁₅H₁₄ClN, exists in a trans configuration with respect to the C=N bond [1.2813 (16) Å]. The dihedral angle between the benzene rings is 52.91 (6)°. The crystal structure is stabilized by weak intermolecular C—H⋯π interactions.

Related literature

For general background to and the pharmacological activity of Schiff base compounds, see: Ittel et al. (2000 ); Shah et al. (1992 ); Cimerman et al. (2000 ); Pandeya et al. (1999 ); More et al. (2001 ); Cimerman & Stefanac (2001 ); Galic et al. (1997 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄ClN
M_r = 243.72
Monoclinic, C c
a = 7.2852 (1) Å
b = 15.2715 (2) Å
c = 11.5382 (1) Å
β = 96.304 (1)°
V = 1275.93 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 100 K
0.40 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.898, T_max = 0.946
14547 measured reflections
3975 independent reflections
3800 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.078
S = 1.04
3975 reflections
156 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1919 Friedel pairs
Flack parameter: 0.04 (4)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯Cg1ⁱ	0.95	2.67	3.3885 (14)	132
C14—H14A⋯Cg1ⁱⁱ	0.98	2.86	3.4853 (14)	124
C2—H2A⋯Cg2ⁱⁱⁱ	0.95	2.73	3.4371 (14)	132
C4—H4A⋯Cg2^iv	0.95	2.80	3.5534 (15)	134
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536811026109/lh5274sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026109/lh5274Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026109/lh5274Isup3.cml

checkCIF report

Comment top

The chemistry of the carbon-nitrogen double bond plays a vital role in the progress of science. Schiff-base compounds have been used as fine chemicals and medical substrates. Recently, multi-dentate complexes of iron and nickel showed high activities of ethylene oligomerization and polymerization (Ittel et al., 2000). Schiff bases have a wide variety of applications in many fields, e.g., biological, inorganic and analytical chemistry (Cimerman et al., 2000). They are known to exhibit potent antibacterial, anticonvulsant, anti-inflammatory activities (Shah et al., 1992). In addition, some Schiff bases show pharmacologically useful activities like anticancer (Pandeya et al., 1999), anti-hypertensive and hypnotic (More et al., 2001) properties. Unfortunately, most Schiff bases are chemically unstable and show a tendency to be involved in various equilibria, like tautomeric interconversions, hydrolysis or formation of ionized species (Cimerman & Stefanac, 2001; Galic et al., 1997). Therefore, successful application of Schiff bases requires a careful study of their characteristics.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are within normal ranges. The title compound exists in trans configuration with respect to the C7═N1 bond [C7═N1 = 1.2813 (16) Å]. The benzene rings (C1-C6 and C8-C13) form a dihedral angle of 52.91 (6)°.

The crystal structure is stabilized by weak intermolecular C12–H12A···Cg1ⁱ, C14–H14A···Cg1ⁱⁱ, C2–H2A···Cg2ⁱⁱⁱ and C4–H4A···Cg2^iv interactions (see Table 1 for symmetry codes), where Cg1 and Cg2 are the centroid of C1-C6 and C8-C13 benzene rings, respectively. No significant classical intermolecular hydrogen bonds are observed.

Related literature top

For general background to and the pharmacological activity of Schiff base compounds, see: Ittel et al. (2000); Shah et al. (1992); Cimerman et al. (2000); Pandeya et al. (1999); More et al. (2001); Cimerman & Stefanac (2001); Galic et al. (1997). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987).

Experimental top

Equimolar amounts of of 4-chloro benzaldehyde and 2,4 dimethyl aniline were dissolved in a minimum amount of ethanol, followed by addition of 2 ml glacial acetic acid. The solution was refluxed for 8 h then cooled to room temperature and poured into ice cold water. The solid product was collected through filtration and then dried at 353 K. The product was dissolved in ethanol, recrystallized and then dried to give colourless crystals. Yield: 75%, m.p. 432-435 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.

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

Crystal data top

C₁₅H₁₄ClN	F(000) = 512
M_r = 243.72	D_x = 1.269 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9896 reflections
a = 7.2852 (1) Å	θ = 2.7–31.0°
b = 15.2715 (2) Å	µ = 0.28 mm⁻¹
c = 11.5382 (1) Å	T = 100 K
β = 96.304 (1)°	Block, colourless
V = 1275.93 (3) Å³	0.40 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3975 independent reflections
Radiation source: fine-focus sealed tube	3800 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 31.1°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.898, T_max = 0.946	k = −17→22
14547 measured reflections	l = −16→16

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)] = 0.031	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0435P)² + 0.4511P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3975 reflections	Δρ_max = 0.32 e Å⁻³
156 parameters	Δρ_min = −0.20 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1919 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (4)

Crystal data top

C₁₅H₁₄ClN	V = 1275.93 (3) Å³
M_r = 243.72	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 7.2852 (1) Å	µ = 0.28 mm⁻¹
b = 15.2715 (2) Å	T = 100 K
c = 11.5382 (1) Å	0.40 × 0.24 × 0.20 mm
β = 96.304 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3975 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3800 reflections with I > 2σ(I)
T_min = 0.898, T_max = 0.946	R_int = 0.020
14547 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.32 e Å⁻³
S = 1.04	Δρ_min = −0.20 e Å⁻³
3975 reflections	Absolute structure: Flack (1983), 1919 Friedel pairs
156 parameters	Absolute structure parameter: 0.04 (4)
2 restraints

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
Cl1	1.00011 (4)	0.620805 (19)	0.24699 (3)	0.02374 (8)
N1	0.98639 (15)	0.21574 (7)	0.00510 (9)	0.0164 (2)
C1	1.10819 (17)	0.36449 (8)	0.25068 (11)	0.0164 (2)
H1A	1.1660	0.3226	0.3036	0.020*
C2	1.09740 (18)	0.45134 (9)	0.28532 (11)	0.0174 (2)
H2A	1.1469	0.4693	0.3612	0.021*
C3	1.01230 (18)	0.51134 (8)	0.20614 (11)	0.0172 (2)
C4	0.93749 (17)	0.48677 (9)	0.09481 (11)	0.0180 (2)
H4A	0.8786	0.5288	0.0425	0.022*
C5	0.95032 (17)	0.39987 (8)	0.06141 (11)	0.0166 (2)
H5A	0.9011	0.3823	−0.0147	0.020*
C6	1.03527 (17)	0.33777 (8)	0.13907 (11)	0.0152 (2)
C7	1.04654 (18)	0.24507 (8)	0.10622 (11)	0.0163 (2)
H7A	1.1011	0.2049	0.1628	0.020*
C8	0.99097 (17)	0.12365 (8)	−0.01051 (11)	0.0153 (2)
C9	1.05963 (17)	0.08957 (8)	−0.11026 (11)	0.0151 (2)
C10	1.05936 (17)	−0.00135 (8)	−0.12576 (11)	0.0164 (2)
H10A	1.1084	−0.0250	−0.1920	0.020*
C11	0.98889 (18)	−0.05863 (8)	−0.04642 (11)	0.0177 (2)
C12	0.91927 (18)	−0.02310 (9)	0.05076 (11)	0.0182 (2)
H12A	0.8702	−0.0608	0.1052	0.022*
C13	0.92063 (18)	0.06723 (8)	0.06920 (11)	0.0172 (2)
H13A	0.8735	0.0905	0.1363	0.021*
C14	1.1312 (2)	0.14980 (9)	−0.19821 (12)	0.0212 (3)
H14A	1.1739	0.1151	−0.2615	0.032*
H14B	1.2342	0.1844	−0.1603	0.032*
H14C	1.0321	0.1892	−0.2301	0.032*
C15	0.9863 (2)	−0.15650 (9)	−0.06663 (13)	0.0244 (3)
H15A	0.8998	−0.1840	−0.0183	0.037*
H15B	1.1104	−0.1803	−0.0457	0.037*
H15C	0.9469	−0.1686	−0.1490	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03157 (16)	0.01487 (12)	0.02478 (15)	0.00105 (13)	0.00319 (11)	−0.00480 (12)
N1	0.0188 (5)	0.0143 (5)	0.0163 (5)	−0.0001 (4)	0.0033 (4)	−0.0014 (4)
C1	0.0181 (6)	0.0165 (5)	0.0144 (5)	−0.0008 (4)	0.0007 (4)	−0.0001 (4)
C2	0.0194 (6)	0.0181 (5)	0.0144 (5)	−0.0012 (5)	0.0011 (4)	−0.0029 (4)
C3	0.0189 (6)	0.0133 (5)	0.0198 (6)	−0.0009 (4)	0.0045 (5)	−0.0034 (4)
C4	0.0188 (6)	0.0163 (6)	0.0187 (6)	0.0012 (4)	0.0010 (4)	0.0005 (4)
C5	0.0187 (6)	0.0161 (5)	0.0149 (5)	0.0001 (4)	0.0015 (4)	−0.0014 (4)
C6	0.0159 (5)	0.0141 (5)	0.0157 (5)	−0.0004 (4)	0.0025 (4)	−0.0017 (4)
C7	0.0168 (5)	0.0145 (5)	0.0178 (5)	0.0002 (4)	0.0024 (4)	−0.0004 (4)
C8	0.0162 (5)	0.0134 (5)	0.0160 (6)	−0.0001 (4)	0.0009 (4)	−0.0009 (4)
C9	0.0164 (5)	0.0149 (5)	0.0138 (5)	−0.0010 (4)	0.0011 (4)	−0.0012 (4)
C10	0.0178 (5)	0.0160 (5)	0.0155 (5)	0.0003 (4)	0.0016 (4)	−0.0025 (4)
C11	0.0185 (6)	0.0146 (5)	0.0191 (6)	−0.0012 (5)	−0.0019 (5)	−0.0005 (4)
C12	0.0198 (6)	0.0168 (6)	0.0180 (6)	−0.0029 (5)	0.0011 (5)	0.0026 (4)
C13	0.0204 (6)	0.0173 (6)	0.0141 (5)	−0.0008 (5)	0.0024 (4)	−0.0005 (4)
C14	0.0272 (7)	0.0173 (6)	0.0205 (6)	−0.0027 (5)	0.0088 (5)	−0.0008 (5)
C15	0.0305 (7)	0.0135 (6)	0.0284 (7)	−0.0016 (5)	−0.0005 (6)	−0.0020 (5)

Geometric parameters (Å, º) top

Cl1—C3	1.7418 (13)	C8—C9	1.4043 (17)
N1—C7	1.2813 (16)	C9—C10	1.3999 (17)
N1—C8	1.4187 (15)	C9—C14	1.5045 (18)
C1—C2	1.3900 (17)	C10—C11	1.4036 (18)
C1—C6	1.3988 (17)	C10—H10A	0.9500
C1—H1A	0.9500	C11—C12	1.3906 (19)
C2—C3	1.3908 (18)	C11—C15	1.5125 (18)
C2—H2A	0.9500	C12—C13	1.3957 (18)
C3—C4	1.3906 (17)	C12—H12A	0.9500
C4—C5	1.3881 (18)	C13—H13A	0.9500
C4—H4A	0.9500	C14—H14A	0.9800
C5—C6	1.4012 (17)	C14—H14B	0.9800
C5—H5A	0.9500	C14—H14C	0.9800
C6—C7	1.4702 (17)	C15—H15A	0.9800
C7—H7A	0.9500	C15—H15B	0.9800
C8—C13	1.3980 (18)	C15—H15C	0.9800

C7—N1—C8	116.85 (11)	C10—C9—C14	121.06 (11)
C2—C1—C6	121.02 (12)	C8—C9—C14	120.48 (11)
C2—C1—H1A	119.5	C9—C10—C11	122.03 (12)
C6—C1—H1A	119.5	C9—C10—H10A	119.0
C1—C2—C3	118.36 (11)	C11—C10—H10A	119.0
C1—C2—H2A	120.8	C12—C11—C10	118.34 (12)
C3—C2—H2A	120.8	C12—C11—C15	120.68 (12)
C4—C3—C2	122.02 (12)	C10—C11—C15	120.98 (12)
C4—C3—Cl1	118.84 (10)	C11—C12—C13	120.76 (12)
C2—C3—Cl1	119.13 (10)	C11—C12—H12A	119.6
C5—C4—C3	118.88 (12)	C13—C12—H12A	119.6
C5—C4—H4A	120.6	C12—C13—C8	120.39 (12)
C3—C4—H4A	120.6	C12—C13—H13A	119.8
C4—C5—C6	120.52 (11)	C8—C13—H13A	119.8
C4—C5—H5A	119.7	C9—C14—H14A	109.5
C6—C5—H5A	119.7	C9—C14—H14B	109.5
C1—C6—C5	119.20 (11)	H14A—C14—H14B	109.5
C1—C6—C7	119.47 (11)	C9—C14—H14C	109.5
C5—C6—C7	121.33 (11)	H14A—C14—H14C	109.5
N1—C7—C6	123.24 (12)	H14B—C14—H14C	109.5
N1—C7—H7A	118.4	C11—C15—H15A	109.5
C6—C7—H7A	118.4	C11—C15—H15B	109.5
C13—C8—C9	120.00 (11)	H15A—C15—H15B	109.5
C13—C8—N1	120.80 (12)	C11—C15—H15C	109.5
C9—C8—N1	119.14 (11)	H15A—C15—H15C	109.5
C10—C9—C8	118.47 (11)	H15B—C15—H15C	109.5

C6—C1—C2—C3	−0.07 (19)	C7—N1—C8—C9	−133.76 (13)
C1—C2—C3—C4	0.46 (19)	C13—C8—C9—C10	−1.42 (18)
C1—C2—C3—Cl1	−179.11 (10)	N1—C8—C9—C10	−178.57 (11)
C2—C3—C4—C5	−0.81 (19)	C13—C8—C9—C14	178.43 (12)
Cl1—C3—C4—C5	178.77 (10)	N1—C8—C9—C14	1.29 (18)
C3—C4—C5—C6	0.76 (19)	C8—C9—C10—C11	1.54 (18)
C2—C1—C6—C5	0.04 (19)	C14—C9—C10—C11	−178.31 (12)
C2—C1—C6—C7	−178.99 (12)	C9—C10—C11—C12	−0.63 (19)
C4—C5—C6—C1	−0.39 (19)	C9—C10—C11—C15	178.60 (11)
C4—C5—C6—C7	178.62 (12)	C10—C11—C12—C13	−0.40 (18)
C8—N1—C7—C6	−174.26 (12)	C15—C11—C12—C13	−179.64 (13)
C1—C6—C7—N1	−178.57 (12)	C11—C12—C13—C8	0.50 (19)
C5—C6—C7—N1	2.4 (2)	C9—C8—C13—C12	0.44 (19)
C7—N1—C8—C13	49.12 (17)	N1—C8—C13—C12	177.53 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···Cg1ⁱ	0.95	2.67	3.3885 (14)	132
C14—H14A···Cg1ⁱⁱ	0.98	2.86	3.4853 (14)	124
C2—H2A···Cg2ⁱⁱⁱ	0.95	2.73	3.4371 (14)	132
C4—H4A···Cg2^iv	0.95	2.80	3.5534 (15)	134

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClN
M_r	243.72
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	7.2852 (1), 15.2715 (2), 11.5382 (1)
β (°)	96.304 (1)
V (Å³)	1275.93 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.40 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.898, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	14547, 3975, 3800
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.727

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.078, 1.04
No. of reflections	3975
No. of parameters	156
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.20
Absolute structure	Flack (1983), 1919 Friedel pairs
Absolute structure parameter	0.04 (4)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···Cg1ⁱ	0.95	2.67	3.3885 (14)	132
C14—H14A···Cg1ⁱⁱ	0.98	2.86	3.4853 (14)	124
C2—H2A···Cg2ⁱⁱⁱ	0.95	2.73	3.4371 (14)	132
C4—H4A···Cg2^iv	0.95	2.80	3.5534 (15)	134

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

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 (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cimerman, Z., Miljanic, S. & Galic, N. (2000). Croat. Chem. Acta, 73, 81–95. CAS Google Scholar
Cimerman, Z. & Stefanac, Z. (2001). Polyhedron, 4, 1755–1760. CrossRef Web of Science Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Galic, N., Cimerman, Z. & Tomisic, V. (1997). Anal. Chim. Acta, 343, 135–143. CrossRef CAS Web of Science Google Scholar
Ittel, S. D., Johnson, L. K. & Brookhart, M. (2000). Chem. Rev. 100, 1169–1203. Web of Science CrossRef PubMed CAS Google Scholar
More, P. G., Bhalvankar, R. B. & Patter, S. C. (2001). J. Indian Chem. Soc. 78, 474–475. CAS Google Scholar
Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Eur. J. Pharm. Sci. 9, 25–31. Web of Science CrossRef PubMed CAS Google Scholar
Shah, S., Vyas, R. & Mehta, R. H. (1992). J. Indian Chem. Soc. 69, 590–596. 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

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 67| Part 8| August 2011| Page o1932

doi:10.1107/S1600536811026109

Open

access