4-Bromo-2-{(E)-3-[1-(hydroxy­imino)eth­yl]phenyl­imino­meth­yl}phenol

Xu, L.; Wu, L.

doi:10.1107/S1600536809048855

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3154

doi:10.1107/S1600536809048855

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4-Bromo-2-{(E)-3-[1-(hydroxyimino)ethyl]phenyliminomethyl}phenol

Li Xu ^a ^* and Lei Wu ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: xuli@mail.lzjtu.cn

(Received 4 November 2009; accepted 17 November 2009; online 21 November 2009)

In the title compound, C₁₅H₁₃BrN₂O₂, he oxime unit adopts an E conformation with respect to the O—H group. A classical intramolecular O—H⋯N hydrogen bond results in the formation of a six-membered ring. The crystal structure is stabilized by intermolecular O—H⋯N hydrogen bonds between the hydroxy groups and the oxime N atoms. In addition, the crystal structure also features short intermolecular Br⋯Br short contacts with a distance of 3.8768 (5) Å.

Related literature

For background to Schiff bases, see: Dong et al. (2007 , 2008 ); Wang et al. 2009 ). For background to oximes, see: Golovnia et al. (2009 ); Liu et al. (2008 ); Dong et al. (2009a ); Öztürk et al. (2009 ). For the synthesis, see: Dong et al. (2009b ).

Experimental

Crystal data

C₁₅H₁₃BrN₂O₂
M_r = 333.18
Monoclinic, P 2₁ /c
a = 17.020 (2) Å
b = 6.1676 (7) Å
c = 13.693 (1) Å
β = 96.461 (1)°
V = 1428.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.88 mm⁻¹
T = 298 K
0.45 × 0.20 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.357, T_max = 0.762
6906 measured reflections
2492 independent reflections
1799 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.100
S = 0.99
2492 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	2.10	2.830 (4)	149
O2—H2⋯N2	0.82	1.91	2.635 (4)	147
Symmetry code: (i) -x, -y+3, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048855/lx2124sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048855/lx2124Isup2.hkl

checkCIF report

Comment top

Schiff base ligands containing oxygen and imine nitrogen atoms have attracted much attention due to their variety of applications as well as their strong coordination capability (Dong et al., 2007; Dong et al., 2008; Wang et al., 2009). The oxime compounds frequently exhibit versatility in organic, inorganic, bioinorganic, pigment, analytical, dyes and medical chemistry (Golovnia et al., 2009; Liu et al., 2008; Dong et al., 2009a; Öztürk et al., 2009). Owing to the importance of oxime-type compounds, we report the crystal structure of the title compound (Fig. 1).

In the crystal structure, all bond lengths and bond angles are in normal ranges. The molecule has a crystallographic inversion centre and the oxime unit adopts an E conformation with respect to the O—H group. The aniline ring (C3–C8) and phenol ring (C10–C15) are almost parallel each other, making a dihedral angle of 2.71 (1)°. The torsion angles of O1—N1—C2—C3 and C5—N2—C9—C10 are 178.5 (3) and -178.8 (3)°, respectively. In the crystal structure, a classical intramolecular O—H···N hydrogen bond forms a six-membered ring (Fig. 2 and Table 1). The crystal packing (Fig. 2) is stabilized by intermolecular O—H···N hydrogen bonds between the hydroxy groups and oxime N atoms, with a O1—H1···N1ⁱ (Table 1). In addition, the crystal structure was further stabilized by weak intermolecular Br···Brⁱⁱ (Fig. 2) short interactions with a distance of 3.8768 (5) Å.

Related literature top

For background to Schiff bases, see: Dong et al. (2007, 2008); Wang et al. 2009). For background to oximes, see: Golovnia et al. (2009); Liu et al. (2008); Dong et al. (2009a); Öztürk et al. (2009). For the synthesis, see: Dong et al. (2009b)

Experimental top

The title compound was synthesized according to an analogous method reported earlier (Dong et al., 2009b). To an ethanol solution (5 ml) of 3-aminophenylethanone oxime (150.2 mg, 1.00 mmol) was added dropwise an ethanol solution (5 ml) of 5-bromosalicylaldehyde (201.1 mg, 1.00 mmol) then the yellow precipitate was obtained. The mixture solution was stirred at 328–333 K for 1 h. After cooling to room temperature, the precipitate was filtered off, dried in vacuo and purified by recrystallization from ethanol of solid. Yield: 54.01%, m. p. 459–461 K. Anal. Calc. for C₁₅H₁₃BrN₂O₂: C, 54.07; H, 3.93; N, 8.41. Found: C, 54.32; H, 4.01; N, 8.81.

Yellow needle-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of dichloromethane at room temperature for about four weeks.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecule structure of the title compound with atom numbering. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. O—H..N and Br···Br interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) -x + 1, y + 1/2, -z + 3/2; (ii) -x + 1, y - 1/2, -z + 3/2; (iii) -x, -y + 3, -z + 1.]

4-Bromo-2-{(E)-3-[1-(hydroxyimino)ethyl]phenyliminomethyl}phenol top

Crystal data top

C₁₅H₁₃BrN₂O₂	F(000) = 672
M_r = 333.18	D_x = 1.549 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 459–461 K
Hall symbol: -p 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.020 (2) Å	Cell parameters from 2173 reflections
b = 6.1676 (7) Å	θ = 2.7–23.8°
c = 13.693 (1) Å	µ = 2.88 mm⁻¹
β = 96.461 (1)°	T = 298 K
V = 1428.3 (3) Å³	Needle-like, yellow
Z = 4	0.45 × 0.20 × 0.10 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2492 independent reflections
Radiation source: fine-focus sealed tube	1799 reflections with I > 2σ(I)
Detector resolution: 10.0 pixels mm^-1	R_int = 0.051
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→14
T_min = 0.357, T_max = 0.762	k = −7→7
6906 measured reflections	l = −15→16

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.100	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0498P)²] where P = (F_o² + 2F_c²)/3
2492 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O₂	V = 1428.3 (3) Å³
M_r = 333.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.020 (2) Å	µ = 2.88 mm⁻¹
b = 6.1676 (7) Å	T = 298 K
c = 13.693 (1) Å	0.45 × 0.20 × 0.10 mm
β = 96.461 (1)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2492 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1799 reflections with I > 2σ(I)
T_min = 0.357, T_max = 0.762	R_int = 0.051
6906 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 0.99	Δρ_max = 0.47 e Å⁻³
2492 reflections	Δρ_min = −0.32 e Å⁻³
182 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
Br	0.46909 (2)	−0.34895 (6)	0.66885 (3)	0.05662 (19)
N1	0.04843 (18)	1.3049 (4)	0.46740 (19)	0.0451 (7)
N2	0.25065 (15)	0.4933 (4)	0.52712 (19)	0.0416 (7)
O1	0.01134 (16)	1.4311 (4)	0.38885 (16)	0.0609 (8)
H1	−0.0096	1.5373	0.4110	0.091*
O2	0.29339 (17)	0.2760 (5)	0.37605 (18)	0.0688 (8)
H2	0.2718	0.3726	0.4044	0.103*
C1	0.0818 (3)	1.0731 (7)	0.3317 (2)	0.0601 (11)
H1A	0.0385	1.1454	0.2940	0.090*
H1B	0.0753	0.9191	0.3247	0.090*
H1C	0.1306	1.1160	0.3084	0.090*
C2	0.0833 (2)	1.1340 (5)	0.4385 (2)	0.0355 (8)
C3	0.12600 (18)	0.9934 (5)	0.5170 (2)	0.0328 (7)
C4	0.16790 (19)	0.8077 (5)	0.4921 (2)	0.0361 (8)
H4	0.1683	0.7723	0.4261	0.043*
C5	0.2089 (2)	0.6749 (5)	0.5637 (2)	0.0372 (8)
C6	0.2088 (2)	0.7269 (6)	0.6638 (2)	0.0457 (9)
H6	0.2355	0.6402	0.7123	0.055*
C7	0.1674 (2)	0.9129 (6)	0.6892 (2)	0.0541 (10)
H7	0.1670	0.9486	0.7551	0.065*
C8	0.1272 (2)	1.0439 (6)	0.6175 (2)	0.0439 (9)
H8	0.1007	1.1664	0.6362	0.053*
C9	0.2887 (2)	0.3533 (5)	0.5848 (2)	0.0402 (8)
H9	0.2886	0.3675	0.6524	0.048*
C10	0.33200 (19)	0.1729 (5)	0.5462 (2)	0.0370 (8)
C11	0.3322 (2)	0.1382 (6)	0.4443 (3)	0.0455 (9)
C12	0.3730 (2)	−0.0397 (6)	0.4104 (3)	0.0554 (10)
H12	0.3726	−0.0625	0.3432	0.067*
C13	0.4141 (2)	−0.1828 (6)	0.4770 (3)	0.0520 (10)
H13	0.4413	−0.3000	0.4544	0.062*
C14	0.4138 (2)	−0.1477 (5)	0.5778 (2)	0.0391 (8)
C15	0.37336 (19)	0.0263 (5)	0.6123 (2)	0.0393 (8)
H15	0.3735	0.0467	0.6797	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0571 (3)	0.0476 (3)	0.0643 (3)	0.01472 (19)	0.0030 (2)	0.00954 (19)
N1	0.056 (2)	0.0395 (17)	0.0372 (15)	0.0112 (15)	−0.0063 (14)	0.0022 (13)
N2	0.0357 (17)	0.0356 (17)	0.0537 (17)	0.0027 (13)	0.0058 (14)	0.0020 (13)
O1	0.083 (2)	0.0526 (16)	0.0436 (13)	0.0295 (15)	−0.0089 (13)	0.0039 (12)
O2	0.078 (2)	0.079 (2)	0.0479 (14)	0.0289 (17)	0.0001 (15)	0.0108 (14)
C1	0.081 (3)	0.062 (2)	0.0367 (19)	0.028 (2)	0.0017 (19)	−0.0001 (18)
C2	0.036 (2)	0.0329 (19)	0.0373 (17)	−0.0002 (15)	0.0027 (15)	−0.0020 (14)
C3	0.0309 (19)	0.0315 (18)	0.0353 (16)	0.0001 (14)	0.0005 (14)	0.0005 (14)
C4	0.037 (2)	0.037 (2)	0.0338 (16)	−0.0039 (15)	0.0021 (15)	−0.0024 (14)
C5	0.0311 (19)	0.0339 (19)	0.0462 (19)	−0.0012 (14)	0.0031 (15)	0.0022 (15)
C6	0.051 (2)	0.043 (2)	0.043 (2)	0.0113 (18)	0.0038 (17)	0.0141 (16)
C7	0.071 (3)	0.058 (2)	0.0331 (18)	0.014 (2)	0.0074 (18)	0.0027 (17)
C8	0.052 (2)	0.040 (2)	0.0395 (18)	0.0097 (17)	0.0060 (17)	0.0024 (16)
C9	0.040 (2)	0.0346 (19)	0.0455 (19)	−0.0010 (16)	0.0020 (16)	−0.0017 (16)
C10	0.0321 (19)	0.0332 (19)	0.0443 (18)	−0.0013 (15)	−0.0016 (15)	0.0004 (15)
C11	0.037 (2)	0.050 (2)	0.048 (2)	0.0033 (17)	0.0018 (17)	0.0052 (18)
C12	0.057 (3)	0.070 (3)	0.0408 (19)	0.012 (2)	0.0101 (18)	−0.0030 (19)
C13	0.051 (3)	0.051 (2)	0.055 (2)	0.0117 (18)	0.0109 (19)	−0.0053 (18)
C14	0.034 (2)	0.0331 (19)	0.050 (2)	−0.0024 (16)	0.0022 (16)	0.0017 (15)
C15	0.038 (2)	0.038 (2)	0.0411 (18)	0.0003 (16)	0.0013 (16)	−0.0041 (15)

Geometric parameters (Å, º) top

Br—C14	1.928 (3)	C4—H4	0.9300
Br—Brⁱ	3.8768 (5)	C5—C6	1.409 (5)
Br—Brⁱⁱ	3.8768 (5)	C6—C7	1.410 (5)
N1—C2	1.293 (4)	C6—H6	0.9300
N1—O1	1.417 (3)	C7—C8	1.390 (5)
N2—C9	1.294 (4)	C7—H7	0.9300
N2—C5	1.446 (4)	C8—H8	0.9300
O1—H1	0.8200	C9—C10	1.466 (4)
O2—C11	1.377 (4)	C9—H9	0.9300
O2—H2	0.8200	C10—C15	1.411 (4)
C1—C2	1.507 (4)	C10—C11	1.411 (5)
C1—H1A	0.9600	C11—C12	1.405 (5)
C1—H1B	0.9600	C12—C13	1.399 (5)
C1—H1C	0.9600	C12—H12	0.9300
C2—C3	1.504 (4)	C13—C14	1.398 (5)
C3—C8	1.409 (4)	C13—H13	0.9300
C3—C4	1.411 (4)	C14—C15	1.387 (4)
C4—C5	1.401 (4)	C15—H15	0.9300

C14—Br—Brⁱ	86.56 (10)	C8—C7—C6	121.3 (3)
C14—Br—Brⁱⁱ	164.58 (10)	C8—C7—H7	119.4
Brⁱ—Br—Brⁱⁱ	105.395 (19)	C6—C7—H7	119.4
C2—N1—O1	113.3 (3)	C7—C8—C3	120.9 (3)
C9—N2—C5	122.5 (3)	C7—C8—H8	119.6
N1—O1—H1	109.5	C3—C8—H8	119.6
C11—O2—H2	109.5	N2—C9—C10	121.6 (3)
C2—C1—H1A	109.5	N2—C9—H9	119.2
C2—C1—H1B	109.5	C10—C9—H9	119.2
H1A—C1—H1B	109.5	C15—C10—C11	118.7 (3)
C2—C1—H1C	109.5	C15—C10—C9	119.3 (3)
H1A—C1—H1C	109.5	C11—C10—C9	122.0 (3)
H1B—C1—H1C	109.5	O2—C11—C12	118.3 (3)
N1—C2—C3	116.9 (3)	O2—C11—C10	121.5 (3)
N1—C2—C1	122.8 (3)	C12—C11—C10	120.1 (3)
C3—C2—C1	120.2 (3)	C13—C12—C11	120.4 (3)
C8—C3—C4	117.6 (3)	C13—C12—H12	119.8
C8—C3—C2	121.6 (3)	C11—C12—H12	119.8
C4—C3—C2	120.8 (3)	C14—C13—C12	119.3 (3)
C5—C4—C3	122.0 (3)	C14—C13—H13	120.4
C5—C4—H4	119.0	C12—C13—H13	120.4
C3—C4—H4	119.0	C15—C14—C13	120.9 (3)
C4—C5—C6	119.5 (3)	C15—C14—Br	120.2 (2)
C4—C5—N2	115.8 (3)	C13—C14—Br	118.9 (2)
C6—C5—N2	124.6 (3)	C14—C15—C10	120.5 (3)
C5—C6—C7	118.7 (3)	C14—C15—H15	119.7
C5—C6—H6	120.6	C10—C15—H15	119.7
C7—C6—H6	120.6

O1—N1—C2—C3	178.5 (3)	N2—C9—C10—C15	179.2 (3)
O1—N1—C2—C1	−1.9 (5)	N2—C9—C10—C11	−2.2 (5)
N1—C2—C3—C8	0.8 (5)	C15—C10—C11—O2	−179.6 (3)
C1—C2—C3—C8	−178.8 (3)	C9—C10—C11—O2	1.8 (5)
N1—C2—C3—C4	−177.9 (3)	C15—C10—C11—C12	0.1 (5)
C1—C2—C3—C4	2.5 (5)	C9—C10—C11—C12	−178.5 (3)
C8—C3—C4—C5	0.6 (5)	O2—C11—C12—C13	179.2 (4)
C2—C3—C4—C5	179.4 (3)	C10—C11—C12—C13	−0.5 (6)
C3—C4—C5—C6	−0.1 (5)	C11—C12—C13—C14	0.4 (6)
C3—C4—C5—N2	−178.6 (3)	C12—C13—C14—C15	0.0 (5)
C9—N2—C5—C4	−177.6 (3)	C12—C13—C14—Br	178.9 (3)
C9—N2—C5—C6	4.0 (5)	Brⁱ—Br—C14—C15	−39.2 (3)
C4—C5—C6—C7	−0.3 (5)	Brⁱⁱ—Br—C14—C15	102.3 (4)
N2—C5—C6—C7	178.1 (3)	Brⁱ—Br—C14—C13	141.9 (3)
C5—C6—C7—C8	0.0 (6)	Brⁱⁱ—Br—C14—C13	−76.7 (5)
C6—C7—C8—C3	0.6 (6)	C13—C14—C15—C10	−0.4 (5)
C4—C3—C8—C7	−0.9 (5)	Br—C14—C15—C10	−179.3 (2)
C2—C3—C8—C7	−179.6 (3)	C11—C10—C15—C14	0.3 (5)
C5—N2—C9—C10	−178.8 (3)	C9—C10—C15—C14	179.0 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱⁱⁱ	0.82	2.10	2.830 (4)	149
O2—H2···N2	0.82	1.91	2.635 (4)	147

Symmetry code: (iii) −x, −y+3, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O₂
M_r	333.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	17.020 (2), 6.1676 (7), 13.693 (1)
β (°)	96.461 (1)
V (Å³)	1428.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.88
Crystal size (mm)	0.45 × 0.20 × 0.10

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.357, 0.762
No. of measured, independent and observed [I > 2σ(I)] reflections	6906, 2492, 1799
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.100, 0.99
No. of reflections	2492
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.32

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	2.10	2.830 (4)	148.5
O2—H2···N2	0.82	1.91	2.635 (4)	147.0

Symmetry code: (i) −x, −y+3, −z+1.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0904-11) and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

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