Bis(2-amino-1,3-benzothia­zole-κN3)dichloridozinc(II) ethanol hemisolvate

Kim, Y.-I.; Kang, S.K.

doi:10.1107/S1600536812001560

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m178-m179

doi:10.1107/S1600536812001560

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Bis(2-amino-1,3-benzothiazole-κN³)dichloridozinc(II) ethanol hemisolvate

Young-Inn Kim ^a and Sung Kwon Kang ^b ^*

^aDepartment of Chemistry Education, Interdisciplinary Program of Advanced Information and Display Materials, and Center for Plastic Information System, Pusan National University, Busan 609-735, Republic of Korea, and ^bDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
^*Correspondence e-mail: skkang@cnu.ac.kr

(Received 31 December 2011; accepted 13 January 2012; online 21 January 2012)

In the title compound, [ZnCl₂(C₇H₆N₂S)₂]·0.5CH₃CH₂OH, the Zn^II atom is coordinated by two N atoms of two 2-aminobenzothiazole ligands and two Cl atoms within a distorted tetrahedral geometry. The dihedral angle between the N/Zn/N and Cl/Zn/Cl planes is 86.22 (7)°. The benzothiazole molecules are almost perpendicular to each other, forming a dihedral angle of 80.20 (8)°. The molecular structure is stabilized by intramolecular N—H⋯Cl hydrogen bonds. In the crystal, intermolecular N—H⋯Cl hydrogen bonds link the molecules into a three-dimensional network. The SQUEEZE procedure in PLATON [Spek (2009 ). Acta Cryst. D65, 148–155] was used to model a disordered ethanol solvent molecule; the calculated unit-cell data allow for the presence of half of this molecule in the asymmetric unit.

Related literature

For the synthesis and structures of related Zn^II and Hg^II metal complexes, see: Kim et al. (2007 , 2010 , 2011 ); Seo et al. (2009 ); Kim & Kang (2010 ). For the biological and photochemical properties of benzothiazole compounds, see: Khan et al. (2011 ); Pavlovic et al. (2007 ); Raposo et al. (2011 ); Saeed et al. (2010 ); Zajac et al. (2008 ).

Experimental

Crystal data

[ZnCl₂(C₇H₆N₂S)₂]·0.5C₂H₆O
M_r = 459.72
Orthorhombic, P c c a
a = 21.0129 (10) Å
b = 11.6013 (5) Å
c = 16.6025 (8) Å
V = 4047.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 1.69 mm⁻¹
T = 296 K
0.13 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.813, T_max = 0.881
16706 measured reflections
4956 independent reflections
2612 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.136
S = 0.88
4956 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N4	2.026 (3)
Zn1—N14	2.028 (3)
Zn1—Cl2	2.2489 (11)
Zn1—Cl3	2.2726 (11)

N4—Zn1—N14	112.24 (12)
Cl2—Zn1—Cl3	112.11 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13A⋯Cl2	0.86	2.46	3.273 (3)	157
N13—H13B⋯Cl3ⁱ	0.86	2.49	3.314 (3)	161
N23—H23A⋯Cl3	0.86	2.54	3.333 (3)	154
N23—H23B⋯Cl2ⁱⁱ	0.86	2.57	3.366 (3)	154
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001560/tk5044sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001560/tk5044Isup2.hkl

checkCIF report

Comment top

Recently, we studied Zn(II) and Hg(II) complexes with nitrogen-containing ligands (Kim et al., 2007; Seo et al., 2009; Kim et al., 2010; Kim & Kang, 2010; Kim et al., 2011) with reference to their luminescent properties, as these can be used as fluorescent brighteners. As a part of our continuous interest in the coordination properties of the nitrogen-containing ligands, herein we report the synthesis of a Zn(II) chloride complex with 2-aminobenzothiazole, (I). Compounds with benzothiazole moiety are also of significant interest due to their biological properties such as anti-tumor and anti-viral (Saeed et al., 2010; Khan et al., 2011) as well as photochemical properties (Pavlovic et al., 2007; Zajac et al., 2008; Raposo et al., 2011).

In (I), Fig. 1, the 2-aminobenzothiazole molecules are almost planar, with r.m.s. deviations of 0.022 and 0.009 Å from the corresponding least-squares plane defined by the ten constituent atoms, respectively. The Zn^II atom is coordinated by two N atoms of benzothiazole ligands and two Cl atoms in a distorted tetrahedral geometry with the dihedral angle of 86.22 (7)° between the N4/Zn1/N14 and Cl2/Zn1/Cl3 planes. The bond distances of N4—C12 [1.338 (4) Å] and N14—C22 [1.317 (4) Å] in the benzothiazole ligands are shorter than those of N4—C5 [1.404 (5) Å] and N14—C15 [1.395 (5) Å], respectively, which is consistent with double bond character in the former (Table 1). The benzothiazole molecules are almost perpendicular to each other with a dihedral angle of 80.20 (8)°. The molecular structure is stabilized by intramolecular N13—H13A···Cl2 and N23—H23A···Cl3 hydrogen bonds (Fig. 1 and Table 2). In the crystal, intermolecular N—H···Cl hydrogen bonds link the molecules into a three-dimensional network (Fig. 2).

Related literature top

For the synthesis and structures of related Zn^II and Hg^II metal complexes, see: Kim et al. (2007, 2010, 2011); Seo et al. (2009); Kim & Kang (2010). For the biological and photochemical properties of benzothiazole compounds, see: Khan et al. (2011); Pavlovic et al. (2007); Raposo et al. (2011); Saeed et al. (2010); Zajac et al. (2008).

Experimental top

All reagents and solvents were purchased from Aldrich and used without further purification. A mixture of ZnCl₂ (0.66 g, 5.0 mmol) and 2-aminobenzothiazole (1.50 g, 10.0 mmol) in ethanol (20 ml) was stirred at room temperature under nitrogen atmosphere. The resulting colourless solution was allowed to stand at room temperature for a week to yield colourless crystals (yield 60.0%) suitable for X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom-numbering scheme and 30% probability ellipsoids. Intramolecular N—H···Cl hydrogen bonds are indicated by dashed lines. The ethanol molecule is not shown.
	Fig. 2. Part of the crystal structure of (I), showing molecules linked by intermolecular N—H···Cl hydrogen bonds (dashed lines). The ethanol molecule is not shown.

Bis(2-amino-1,3-benzothiazole-κN³)dichloridozinc(II) ethanol hemisolvate top

Crystal data top

[ZnCl₂(C₇H₆N₂S)₂]·0.5C₂H₆O	F(000) = 1760
M_r = 459.72	D_x = 1.509 Mg m⁻³
Orthorhombic, Pcca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2ac	Cell parameters from 1986 reflections
a = 21.0129 (10) Å	θ = 3.0–24.3°
b = 11.6013 (5) Å	µ = 1.69 mm⁻¹
c = 16.6025 (8) Å	T = 296 K
V = 4047.3 (3) Å³	Block, colourless
Z = 8	0.13 × 0.1 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2612 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −27→8
T_min = 0.813, T_max = 0.881	k = −15→12
16706 measured reflections	l = −19→21
4956 independent 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.0724P)²] where P = (F_o² + 2F_c²)/3
4956 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[ZnCl₂(C₇H₆N₂S)₂]·0.5C₂H₆O	V = 4047.3 (3) Å³
M_r = 459.72	Z = 8
Orthorhombic, Pcca	Mo Kα radiation
a = 21.0129 (10) Å	µ = 1.69 mm⁻¹
b = 11.6013 (5) Å	T = 296 K
c = 16.6025 (8) Å	0.13 × 0.1 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4956 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2612 reflections with I > 2σ(I)
T_min = 0.813, T_max = 0.881	R_int = 0.058
16706 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 0.88	Δρ_max = 0.39 e Å⁻³
4956 reflections	Δρ_min = −0.34 e Å⁻³
208 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
Zn1	0.387172 (17)	0.61071 (4)	0.10299 (3)	0.04953 (16)
Cl2	0.33663 (4)	0.61006 (11)	0.22239 (6)	0.0701 (3)
Cl3	0.42382 (4)	0.43298 (9)	0.06892 (7)	0.0598 (3)
N4	0.32592 (12)	0.6503 (3)	0.01289 (18)	0.0477 (7)
C5	0.34802 (15)	0.6653 (3)	−0.0662 (2)	0.0462 (8)
C6	0.41141 (18)	0.6731 (4)	−0.0882 (2)	0.0569 (10)
H6	0.4435	0.6673	−0.0499	0.068*
C7	0.42565 (19)	0.6899 (4)	−0.1684 (3)	0.0624 (11)
H7	0.4681	0.6945	−0.184	0.075*
C8	0.3791 (2)	0.6999 (4)	−0.2255 (3)	0.0766 (13)
H8	0.3899	0.7119	−0.2791	0.092*
C9	0.3160 (2)	0.6922 (4)	−0.2033 (3)	0.0758 (13)
H9	0.2841	0.6989	−0.2418	0.091*
C10	0.30062 (17)	0.6744 (4)	−0.1237 (3)	0.0565 (10)
S11	0.22578 (4)	0.66284 (11)	−0.07852 (7)	0.0681 (3)
C12	0.26227 (15)	0.6488 (3)	0.0152 (2)	0.0519 (9)
N13	0.22837 (13)	0.6396 (3)	0.0822 (2)	0.0682 (10)
H13A	0.2473	0.6342	0.128	0.082*
H13B	0.1875	0.6391	0.0799	0.082*
N14	0.45956 (13)	0.7257 (3)	0.11147 (19)	0.0510 (8)
C15	0.45232 (18)	0.8447 (4)	0.1039 (2)	0.0563 (10)
C16	0.3996 (2)	0.9016 (4)	0.0752 (4)	0.0839 (15)
H16	0.3638	0.8601	0.0595	0.101*
C17	0.3998 (3)	1.0218 (5)	0.0695 (4)	0.1028 (18)
H17	0.3648	1.0607	0.0486	0.123*
C18	0.4536 (4)	1.0833 (5)	0.0957 (4)	0.1039 (19)
H18	0.4536	1.1635	0.0936	0.125*
C19	0.5060 (3)	1.0260 (5)	0.1243 (4)	0.0920 (16)
H19	0.542	1.0665	0.1408	0.11*
C20	0.5045 (2)	0.9079 (4)	0.1283 (3)	0.0689 (12)
S21	0.56461 (5)	0.81677 (11)	0.16229 (8)	0.0794 (4)
C22	0.51607 (16)	0.6994 (4)	0.1405 (2)	0.0526 (9)
N23	0.53666 (14)	0.5938 (3)	0.1541 (2)	0.0673 (10)
H23A	0.5125	0.5358	0.1439	0.081*
H23B	0.5742	0.583	0.1732	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0339 (2)	0.0592 (3)	0.0555 (3)	−0.00259 (18)	−0.00195 (16)	−0.0009 (2)
Cl2	0.0450 (5)	0.1092 (9)	0.0562 (6)	0.0047 (5)	0.0029 (4)	0.0017 (6)
Cl3	0.0395 (4)	0.0593 (6)	0.0807 (7)	0.0003 (4)	0.0012 (4)	−0.0048 (5)
N4	0.0336 (13)	0.0584 (19)	0.051 (2)	−0.0019 (13)	−0.0030 (12)	−0.0022 (15)
C5	0.0385 (17)	0.044 (2)	0.056 (2)	−0.0035 (15)	−0.0026 (15)	−0.0041 (18)
C6	0.047 (2)	0.063 (3)	0.062 (3)	0.0010 (18)	0.0038 (17)	−0.002 (2)
C7	0.056 (2)	0.069 (3)	0.062 (3)	−0.0080 (19)	0.013 (2)	−0.010 (2)
C8	0.078 (3)	0.098 (4)	0.053 (3)	−0.019 (3)	0.008 (2)	−0.006 (3)
C9	0.070 (3)	0.103 (4)	0.055 (3)	−0.015 (3)	−0.015 (2)	−0.006 (3)
C10	0.043 (2)	0.066 (3)	0.060 (3)	−0.0058 (18)	−0.0032 (16)	0.000 (2)
S11	0.0404 (5)	0.0954 (9)	0.0686 (7)	−0.0065 (5)	−0.0123 (4)	0.0040 (6)
C12	0.0363 (17)	0.057 (2)	0.063 (3)	0.0000 (15)	−0.0028 (16)	−0.003 (2)
N13	0.0321 (15)	0.108 (3)	0.064 (2)	−0.0072 (16)	0.0005 (14)	0.001 (2)
N14	0.0403 (15)	0.053 (2)	0.059 (2)	−0.0049 (14)	−0.0028 (13)	−0.0030 (15)
C15	0.054 (2)	0.056 (3)	0.059 (3)	−0.0036 (19)	0.0036 (18)	−0.002 (2)
C16	0.080 (3)	0.062 (3)	0.109 (4)	−0.001 (2)	−0.017 (3)	−0.006 (3)
C17	0.102 (4)	0.070 (4)	0.136 (5)	0.018 (3)	−0.015 (4)	−0.004 (3)
C18	0.129 (5)	0.055 (3)	0.128 (5)	−0.008 (3)	0.014 (4)	−0.007 (3)
C19	0.083 (4)	0.074 (4)	0.119 (5)	−0.018 (3)	0.000 (3)	−0.010 (3)
C20	0.076 (3)	0.054 (3)	0.077 (3)	−0.015 (2)	0.008 (2)	−0.009 (2)
S21	0.0532 (6)	0.0765 (8)	0.1084 (10)	−0.0193 (5)	−0.0102 (6)	−0.0122 (7)
C22	0.0419 (19)	0.063 (3)	0.053 (2)	−0.0077 (18)	0.0060 (16)	−0.005 (2)
N23	0.0423 (16)	0.068 (3)	0.092 (3)	0.0004 (16)	−0.0166 (17)	−0.005 (2)

Geometric parameters (Å, º) top

Zn1—N4	2.026 (3)	N13—H13A	0.86
Zn1—N14	2.028 (3)	N13—H13B	0.86
Zn1—Cl2	2.2489 (11)	N14—C22	1.317 (4)
Zn1—Cl3	2.2726 (11)	N14—C15	1.395 (5)
N4—C12	1.338 (4)	C15—C16	1.374 (6)
N4—C5	1.404 (5)	C15—C20	1.380 (6)
C5—C10	1.384 (5)	C16—C17	1.399 (7)
C5—C6	1.384 (5)	C16—H16	0.93
C6—C7	1.378 (5)	C17—C18	1.405 (8)
C6—H6	0.93	C17—H17	0.93
C7—C8	1.368 (6)	C18—C19	1.373 (8)
C7—H7	0.93	C18—H18	0.93
C8—C9	1.379 (6)	C19—C20	1.372 (6)
C8—H8	0.93	C19—H19	0.93
C9—C10	1.375 (6)	C20—S21	1.741 (5)
C9—H9	0.93	S21—C22	1.740 (4)
C10—S11	1.748 (4)	C22—N23	1.318 (5)
S11—C12	1.742 (4)	N23—H23A	0.86
C12—N13	1.326 (5)	N23—H23B	0.86

N4—Zn1—N14	112.24 (12)	C12—N13—H13A	120
N4—Zn1—Cl2	110.59 (8)	C12—N13—H13B	120
N14—Zn1—Cl2	107.17 (9)	H13A—N13—H13B	120
N4—Zn1—Cl3	103.73 (9)	C22—N14—C15	111.1 (3)
N14—Zn1—Cl3	111.09 (9)	C22—N14—Zn1	123.3 (3)
Cl2—Zn1—Cl3	112.11 (5)	C15—N14—Zn1	124.3 (2)
C12—N4—C5	111.0 (3)	C16—C15—C20	119.2 (4)
C12—N4—Zn1	127.7 (3)	C16—C15—N14	126.5 (4)
C5—N4—Zn1	120.6 (2)	C20—C15—N14	114.4 (4)
C10—C5—C6	120.4 (4)	C15—C16—C17	120.0 (5)
C10—C5—N4	114.7 (3)	C15—C16—H16	120
C6—C5—N4	125.0 (3)	C17—C16—H16	120
C7—C6—C5	118.2 (4)	C16—C17—C18	119.2 (5)
C7—C6—H6	120.9	C16—C17—H17	120.4
C5—C6—H6	120.9	C18—C17—H17	120.4
C8—C7—C6	121.8 (4)	C19—C18—C17	120.5 (5)
C8—C7—H7	119.1	C19—C18—H18	119.8
C6—C7—H7	119.1	C17—C18—H18	119.8
C7—C8—C9	119.8 (4)	C20—C19—C18	118.8 (5)
C7—C8—H8	120.1	C20—C19—H19	120.6
C9—C8—H8	120.1	C18—C19—H19	120.6
C10—C9—C8	119.5 (4)	C19—C20—C15	122.3 (5)
C10—C9—H9	120.2	C19—C20—S21	127.2 (4)
C8—C9—H9	120.2	C15—C20—S21	110.4 (3)
C9—C10—C5	120.3 (3)	C22—S21—C20	89.0 (2)
C9—C10—S11	129.5 (3)	N14—C22—N23	125.0 (3)
C5—C10—S11	110.2 (3)	N14—C22—S21	115.0 (3)
C12—S11—C10	89.70 (17)	N23—C22—S21	119.9 (3)
N13—C12—N4	124.2 (3)	C22—N23—H23A	120
N13—C12—S11	121.4 (3)	C22—N23—H23B	120
N4—C12—S11	114.4 (3)	H23A—N23—H23B	120

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···Cl2	0.86	2.46	3.273 (3)	157
N13—H13B···Cl3ⁱ	0.86	2.49	3.314 (3)	161
N23—H23A···Cl3	0.86	2.54	3.333 (3)	154
N23—H23B···Cl2ⁱⁱ	0.86	2.57	3.366 (3)	154

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₇H₆N₂S)₂]·0.5C₂H₆O
M_r	459.72
Crystal system, space group	Orthorhombic, Pcca
Temperature (K)	296
a, b, c (Å)	21.0129 (10), 11.6013 (5), 16.6025 (8)
V (Å³)	4047.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.69
Crystal size (mm)	0.13 × 0.1 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.813, 0.881
No. of measured, independent and observed [I > 2σ(I)] reflections	16706, 4956, 2612
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.136, 0.88
No. of reflections	4956
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.34

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Zn1—N4	2.026 (3)	N4—C12	1.338 (4)
Zn1—N14	2.028 (3)	N4—C5	1.404 (5)
Zn1—Cl2	2.2489 (11)	N14—C22	1.317 (4)
Zn1—Cl3	2.2726 (11)	N14—C15	1.395 (5)

N4—Zn1—N14	112.24 (12)	Cl2—Zn1—Cl3	112.11 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···Cl2	0.86	2.46	3.273 (3)	157
N13—H13B···Cl3ⁱ	0.86	2.49	3.314 (3)	161
N23—H23A···Cl3	0.86	2.54	3.333 (3)	154
N23—H23B···Cl2ⁱⁱ	0.86	2.57	3.366 (3)	154

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

Acknowledgements

This work was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 20110003799).

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