N,N′-(4-Chloro­benzyl­idene)dipyrimidin-2-amine

Tabatabaee, M.; Masoodpour, L.; Gassemzadeh, M.; Hakimi, F.

doi:10.1107/S1600536809045243

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2979

doi:10.1107/S1600536809045243

Open

access

N,N′-(4-Chlorobenzylidene)dipyrimidin-2-amine

Masoumeh Tabatabaee,^a ^* Leila Masoodpour,^a Mitra Gassemzadeh ^a and Fatemeh Hakimi ^a

^aDepartment of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran
^*Correspondence e-mail: tabatabaee45m@yahoo.com

(Received 9 September 2009; accepted 28 October 2009; online 4 November 2009)

The title compound, C₁₅H₁₃ClN₆, contains two pyrimidine rings and one benzene ring, where the dihedral angle between the planes through the pyrimidine rings is 81.57 (10)°, and those between the pyrimidine rings and the benzene ring are 84.02 (8) and 89.46 (7)°, indicating that the three rings are almost perpendicular. In the crystal, intermolecular N—H⋯N hydrogen bonds link the molecules into infinite chains along (100).

Related literature

For the biological activity of pyrimidine derivatives, see: Onal & Altral (1999 ); Ponticelli et al. (1999 ). For studies of the reactions of heterocyclic amines with aromatic aldehydes to prepare new ligands, see: Tabatabaee et al. (2006 ); Tabatabaee, Ghassemzadeh, Dehghan et al. (2007 ); Tabatabaee, Ghassemzadeh, Zarabi et al. (2007 ); Tabatabaee, Ghassemzadeh et al. (2008 ); Tabatabaee, Hakimi et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₃ClN₆
M_r = 312.76
Monoclinic, P 2₁ /n
a = 9.6030 (14) Å
b = 10.5706 (15) Å
c = 14.792 (2) Å
β = 100.331 (3)°
V = 1477.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 K
0.17 × 0.15 × 0.14 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.950, T_max = 0.964
15899 measured reflections
3924 independent reflections
2429 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.163
S = 1.01
3924 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N3ⁱ	0.84 (3)	2.20 (3)	3.033 (3)	174 (3)
N4—H4N⋯N6ⁱⁱ	0.83 (3)	2.24 (3)	3.057 (3)	172 (3)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536809045243/ez2187sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045243/ez2187Isup2.hkl

checkCIF report

Comment top

Pyrimidine derivatives represent a class of heterocycles of great importance. Many pyrimidines, or their derivatives, possess remarkable biological activity and have been widely used in medicinal and industrial applications (Onal & Altral, 1999; Ponticelli et al., 1999). In the continuation of our recent work on the reactions of heterocyclic amines with aromatic aldehydes to prepare new ligands (Tabatabaee et al., 2006; Tabatabaee, Ghassemzadeh, Dehghan et al., 2007; Tabatabaee, Ghassemzadeh, Zarabi et al., 2007; Tabatabaee, Ghassemzadeh et al., 2008; Tabatabaee, Hakimi et al., 2008) we report our results on the reaction of 2-aminopyrimidine and 4-chlorobenzaldehyde in this communication.

The crystal structure of (I) (Fig. 1) shows that one molecule of 4-chlorobenzaldehyde reacted with two molecules of 2-aminopyrimidine to form (I). Bond lengths and angles are unexceptional. The compound contains two pyrimidine (A:N2/C8/N3/C11/C10/C9 and B: N5/C12/N6/C15/C14/C13) and one benzene (C: C2/C3/C4/C5/C6/C7) rings, The dihedral angles formed by the planes through A and B is 81.57 (10)°, through A and C is 84.02 (8)° and through B and C is 89.49 (7)°, indicating that the three rings are almost perpendicular.

Intermolecular N—H···N hydrogen bonds link the molecules into infinite one-dimensional chains along (100) (Table 1 and Fig 2). An interesting feature of compound (I) is the presence of C—H···π stacking interactions between C—H groups from one molecule and aromatic rings on adjacent molecules. The C—H···π distance is 2.89 Å for C9—H9A···Cg3 (Cg3: C2/C3—C7), with an angle of 133.21° and 2.99 Å for C4—H4A^···Cg1 (Cg1: N2/C8 — C9) with an angle of 132.27° (Fig. 3).

Related literature top

For the biological activity of pyrimidine derivatives, see: Onal & Altral (1999); Ponticelli et al. (1999). For studies of the reactions of heterocyclic amines with aromatic aldehyde to prepare new ligands, see: Tabatabaee et al. (2006); Tabatabaee, Ghassemzadeh, Dehghan et al. (2007); Tabatabaee, Ghassemzadeh, Zarabi et al. (2007); Tabatabaee, Ghassemzadeh et al. (2008); Tabatabaee, Hakimi et al. (2008).

Experimental top

A solution of 2-aminopyrimidine (0.951 g, 10 mmol) in EtOH (10 ml) was treated with 4- chlorobenzaldehyde (0.7 g, 5 mmol) and the resulting mixture was acidified with 37% hydrochloric acid (0.2 ml). The reaction mixture was refluxed for 12 h. The solid residue was filtered and the filtrate was kept at 293 K. Colorless crystals of the title compound were obtained after a few days (yield 92%).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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 (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of (I), molecules are linked into infinite one dimensional chains by hydrogen-bond interactions (dashed lines).
	Fig. 3. Intermolecular C—H···π interactions (dashed lines) between aromatic rings of adjacent molecules.

N,N'-(4-Chlorobenzylidene)dipyrimidin-2-amine top

Crystal data top

C₁₅H₁₃ClN₆	F(000) = 648
M_r = 312.76	D_x = 1.406 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 697 reflections
a = 9.6030 (14) Å	θ = 3–30°
b = 10.5706 (15) Å	µ = 0.26 mm⁻¹
c = 14.792 (2) Å	T = 120 K
β = 100.331 (3)°	Prism, colorless
V = 1477.2 (4) Å³	0.17 × 0.15 × 0.14 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3924 independent reflections
Radiation source: fine-focus sealed tube	2429 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 29.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −13→13
T_min = 0.950, T_max = 0.964	k = −14→14
15899 measured reflections	l = −20→20

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)] = 0.061	Hydrogen site location: mixed
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.061P)² + 1.85P] where P = (F_o² + 2F_c²)/3
3924 reflections	(Δ/σ)_max = 0.001
207 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₆	V = 1477.2 (4) Å³
M_r = 312.76	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6030 (14) Å	µ = 0.26 mm⁻¹
b = 10.5706 (15) Å	T = 120 K
c = 14.792 (2) Å	0.17 × 0.15 × 0.14 mm
β = 100.331 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3924 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	2429 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.964	R_int = 0.063
15899 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.55 e Å⁻³
3924 reflections	Δρ_min = −0.28 e Å⁻³
207 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
Cl1	−0.02192 (8)	0.53784 (7)	0.18886 (5)	0.0355 (2)
N1	0.3768 (2)	0.1522 (2)	0.49990 (15)	0.0255 (5)
H1N	0.372 (3)	0.073 (3)	0.4970 (19)	0.026 (7)*
N2	0.5083 (2)	0.3334 (2)	0.53797 (15)	0.0288 (5)
N3	0.6177 (2)	0.13385 (19)	0.51466 (14)	0.0252 (5)
N4	0.1456 (2)	0.1274 (2)	0.53239 (15)	0.0271 (5)
H4N	0.100 (3)	0.085 (3)	0.490 (2)	0.026 (7)*
N5	0.1916 (2)	0.1776 (2)	0.68744 (15)	0.0297 (5)
N6	0.0426 (2)	0.0032 (2)	0.62930 (15)	0.0324 (5)
C1	0.2469 (3)	0.2170 (2)	0.51066 (17)	0.0236 (5)
H1A	0.2701	0.2771	0.5635	0.028*
C2	0.1814 (3)	0.2927 (2)	0.42613 (17)	0.0231 (5)
C3	0.2361 (3)	0.2959 (2)	0.34541 (18)	0.0281 (6)
H3A	0.3172	0.2468	0.3403	0.034*
C4	0.1729 (3)	0.3708 (3)	0.27187 (17)	0.0305 (6)
H4A	0.2106	0.3727	0.2168	0.037*
C5	0.0551 (3)	0.4423 (2)	0.27932 (17)	0.0257 (5)
C6	−0.0013 (3)	0.4405 (2)	0.35850 (18)	0.0274 (5)
H6A	−0.0824	0.4898	0.3633	0.033*
C7	0.0623 (3)	0.3653 (2)	0.43127 (17)	0.0263 (5)
H7A	0.0235	0.3635	0.4860	0.032*
C8	0.5041 (3)	0.2088 (2)	0.51871 (16)	0.0227 (5)
C9	0.6373 (3)	0.3841 (3)	0.5586 (2)	0.0346 (6)
H9A	0.6452	0.4713	0.5741	0.041*
C10	0.7596 (3)	0.3161 (3)	0.5585 (2)	0.0353 (7)
H10A	0.8505	0.3537	0.5745	0.042*
C11	0.7431 (3)	0.1905 (3)	0.53381 (18)	0.0295 (6)
H11A	0.8254	0.1421	0.5303	0.035*
C12	0.1273 (3)	0.1023 (3)	0.61980 (17)	0.0266 (5)
C13	0.1706 (3)	0.1484 (3)	0.77168 (19)	0.0346 (6)
H13A	0.2127	0.2005	0.8215	0.041*
C14	0.0906 (3)	0.0461 (3)	0.7899 (2)	0.0406 (7)
H14A	0.0802	0.0247	0.8507	0.049*
C15	0.0269 (3)	−0.0232 (3)	0.7149 (2)	0.0406 (7)
H15A	−0.0309	−0.0929	0.7247	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0406 (4)	0.0320 (4)	0.0312 (4)	0.0008 (3)	−0.0014 (3)	0.0066 (3)
N1	0.0227 (11)	0.0213 (11)	0.0316 (12)	−0.0002 (9)	0.0021 (9)	0.0004 (9)
N2	0.0303 (12)	0.0236 (11)	0.0335 (12)	−0.0039 (9)	0.0081 (9)	−0.0030 (9)
N3	0.0245 (11)	0.0236 (11)	0.0263 (11)	−0.0021 (9)	0.0016 (8)	−0.0015 (9)
N4	0.0272 (11)	0.0300 (12)	0.0229 (11)	−0.0074 (9)	0.0016 (9)	−0.0006 (9)
N5	0.0288 (12)	0.0333 (12)	0.0267 (11)	−0.0018 (10)	0.0043 (9)	−0.0002 (9)
N6	0.0310 (12)	0.0394 (13)	0.0256 (11)	−0.0081 (10)	0.0021 (9)	0.0041 (10)
C1	0.0227 (12)	0.0234 (12)	0.0238 (12)	−0.0010 (10)	0.0021 (9)	−0.0017 (10)
C2	0.0237 (12)	0.0221 (12)	0.0235 (12)	−0.0048 (10)	0.0042 (9)	0.0003 (10)
C3	0.0300 (14)	0.0268 (13)	0.0287 (13)	0.0029 (11)	0.0082 (11)	−0.0007 (11)
C4	0.0366 (15)	0.0345 (15)	0.0220 (12)	−0.0018 (12)	0.0098 (11)	−0.0007 (11)
C5	0.0288 (13)	0.0235 (12)	0.0230 (12)	−0.0030 (10)	−0.0001 (10)	−0.0001 (10)
C6	0.0238 (12)	0.0273 (13)	0.0300 (13)	0.0005 (10)	0.0023 (10)	−0.0025 (10)
C7	0.0246 (13)	0.0306 (13)	0.0245 (12)	−0.0010 (11)	0.0065 (10)	−0.0003 (10)
C8	0.0261 (13)	0.0221 (12)	0.0199 (12)	−0.0036 (10)	0.0039 (10)	0.0014 (10)
C9	0.0353 (15)	0.0254 (13)	0.0458 (16)	−0.0095 (12)	0.0147 (13)	−0.0094 (12)
C10	0.0306 (14)	0.0339 (15)	0.0437 (16)	−0.0109 (12)	0.0128 (12)	−0.0118 (13)
C11	0.0267 (13)	0.0306 (14)	0.0316 (14)	−0.0019 (11)	0.0065 (11)	−0.0009 (11)
C12	0.0225 (12)	0.0311 (14)	0.0256 (13)	0.0013 (11)	0.0028 (10)	0.0023 (11)
C13	0.0317 (15)	0.0410 (16)	0.0291 (14)	0.0026 (12)	0.0004 (11)	−0.0044 (12)
C14	0.0368 (16)	0.059 (2)	0.0258 (14)	−0.0061 (15)	0.0058 (12)	0.0057 (14)
C15	0.0346 (16)	0.0541 (19)	0.0330 (15)	−0.0126 (14)	0.0059 (12)	0.0119 (14)

Geometric parameters (Å, º) top

Cl1—C5	1.732 (3)	C3—C4	1.394 (4)
N1—C8	1.345 (3)	C3—H3A	0.9500
N1—C1	1.456 (3)	C4—C5	1.381 (4)
N1—H1N	0.84 (3)	C4—H4A	0.9500
N2—C9	1.334 (3)	C5—C6	1.376 (4)
N2—C8	1.347 (3)	C6—C7	1.388 (4)
N3—C11	1.329 (3)	C6—H6A	0.9500
N3—C8	1.358 (3)	C7—H7A	0.9500
N4—C12	1.362 (3)	C9—C10	1.377 (4)
N4—C1	1.435 (3)	C9—H9A	0.9500
N4—H4N	0.83 (3)	C10—C11	1.378 (4)
N5—C13	1.334 (4)	C10—H10A	0.9500
N5—C12	1.339 (3)	C11—H11A	0.9500
N6—C15	1.331 (4)	C13—C14	1.381 (4)
N6—C12	1.349 (3)	C13—H13A	0.9500
C1—C2	1.523 (3)	C14—C15	1.378 (4)
C1—H1A	1.0000	C14—H14A	0.9500
C2—C3	1.389 (3)	C15—H15A	0.9500
C2—C7	1.390 (3)

C8—N1—C1	122.2 (2)	C5—C6—H6A	120.6
C8—N1—H1N	120 (2)	C7—C6—H6A	120.6
C1—N1—H1N	116 (2)	C6—C7—C2	121.7 (2)
C9—N2—C8	115.6 (2)	C6—C7—H7A	119.2
C11—N3—C8	115.6 (2)	C2—C7—H7A	119.2
C12—N4—C1	123.3 (2)	N1—C8—N2	118.0 (2)
C12—N4—H4N	118 (2)	N1—C8—N3	116.1 (2)
C1—N4—H4N	119 (2)	N2—C8—N3	125.9 (2)
C13—N5—C12	115.7 (2)	N2—C9—C10	123.2 (3)
C15—N6—C12	115.8 (2)	N2—C9—H9A	118.4
N4—C1—N1	110.0 (2)	C10—C9—H9A	118.4
N4—C1—C2	109.5 (2)	C9—C10—C11	116.5 (3)
N1—C1—C2	113.2 (2)	C9—C10—H10A	121.8
N4—C1—H1A	108.0	C11—C10—H10A	121.8
N1—C1—H1A	108.0	N3—C11—C10	123.1 (3)
C2—C1—H1A	108.0	N3—C11—H11A	118.4
C3—C2—C7	118.4 (2)	C10—C11—H11A	118.4
C3—C2—C1	123.7 (2)	N5—C12—N6	126.1 (2)
C7—C2—C1	117.9 (2)	N5—C12—N4	118.2 (2)
C2—C3—C4	120.4 (2)	N6—C12—N4	115.7 (2)
C2—C3—H3A	119.8	N5—C13—C14	123.1 (3)
C4—C3—H3A	119.8	N5—C13—H13A	118.5
C5—C4—C3	119.8 (2)	C14—C13—H13A	118.5
C5—C4—H4A	120.1	C15—C14—C13	116.2 (3)
C3—C4—H4A	120.1	C15—C14—H14A	121.9
C6—C5—C4	120.9 (2)	C13—C14—H14A	121.9
C6—C5—Cl1	119.1 (2)	N6—C15—C14	123.0 (3)
C4—C5—Cl1	120.0 (2)	N6—C15—H15A	118.5
C5—C6—C7	118.8 (2)	C14—C15—H15A	118.5

C12—N4—C1—N1	96.1 (3)	C1—N1—C8—N3	173.6 (2)
C12—N4—C1—C2	−139.0 (2)	C9—N2—C8—N1	178.2 (2)
C8—N1—C1—N4	−150.6 (2)	C9—N2—C8—N3	−3.1 (4)
C8—N1—C1—C2	86.6 (3)	C11—N3—C8—N1	−179.7 (2)
N4—C1—C2—C3	−120.7 (3)	C11—N3—C8—N2	1.6 (4)
N1—C1—C2—C3	2.5 (3)	C8—N2—C9—C10	1.5 (4)
N4—C1—C2—C7	61.2 (3)	N2—C9—C10—C11	1.2 (4)
N1—C1—C2—C7	−175.7 (2)	C8—N3—C11—C10	1.5 (4)
C7—C2—C3—C4	0.3 (4)	C9—C10—C11—N3	−2.8 (4)
C1—C2—C3—C4	−177.9 (2)	C13—N5—C12—N6	1.4 (4)
C2—C3—C4—C5	0.0 (4)	C13—N5—C12—N4	−179.7 (2)
C3—C4—C5—C6	−0.2 (4)	C15—N6—C12—N5	−2.5 (4)
C3—C4—C5—Cl1	178.8 (2)	C15—N6—C12—N4	178.6 (3)
C4—C5—C6—C7	0.1 (4)	C1—N4—C12—N5	10.1 (4)
Cl1—C5—C6—C7	−179.0 (2)	C1—N4—C12—N6	−170.9 (2)
C5—C6—C7—C2	0.3 (4)	C12—N5—C13—C14	1.4 (4)
C3—C2—C7—C6	−0.4 (4)	N5—C13—C14—C15	−2.8 (5)
C1—C2—C7—C6	177.8 (2)	C12—N6—C15—C14	0.8 (5)
C1—N1—C8—N2	−7.6 (3)	C13—C14—C15—N6	1.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3ⁱ	0.84 (3)	2.20 (3)	3.033 (3)	174 (3)
N4—H4N···N6ⁱⁱ	0.83 (3)	2.24 (3)	3.057 (3)	172 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₆
M_r	312.76
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	9.6030 (14), 10.5706 (15), 14.792 (2)
β (°)	100.331 (3)
V (Å³)	1477.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.17 × 0.15 × 0.14

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.950, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	15899, 3924, 2429
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.163, 1.01
No. of reflections	3924
No. of parameters	207
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.28

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3ⁱ	0.84 (3)	2.20 (3)	3.033 (3)	174 (3)
N4—H4N···N6ⁱⁱ	0.83 (3)	2.24 (3)	3.057 (3)	172 (3)

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

Acknowledgements

The authors express their appreciation to the Islamic Azad University, Yazd Branch, for financial support of this work.

References

Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Onal, Z. & Altral, B. (1999). Turk. J. Chem. 23, 401–405. CAS Google Scholar
Ponticelli, G., Spanu, A. M. T., Cocco, M. T. & Onnis, V. (1999). Transition Met. Chem. 24, 370–372. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tabatabaee, M., Ghassemzadeh, M., Dehghan, A. R., Khavasi, H. R. & Heravi, M. M. (2007). Acta Cryst. E63, o42–o43. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tabatabaee, M., Ghassemzadeh, M. & Soleimani, N. (2008). Anal. Sci. 24, x173–x174. CAS Google Scholar
Tabatabaee, M., Ghassemzadeh, M., Zarabi, B., Heravi, M. M., Anary-Abbasinejad, M. & Neumüller, B. (2007). Phosphorus Sulfur Silicon Relat. Elem. 182, 677–686. Web of Science CSD CrossRef CAS Google Scholar
Tabatabaee, M., Ghassemzadeh, M., Zarabi, B. & Neumüller, B. (2006). Z. Naturforsch. Teil B, 61, 1421–1425. CAS Google Scholar
Tabatabaee, M., Hakimi, F., Roshani, M., Mirjalili, M. & Kavasi, H. R. (2008). Acta Cryst. E64, o2112. Web of Science CSD CrossRef IUCr Journals Google Scholar