[N′-(5-Bromo-2-oxidobenzyl­idene-κO)-2-chloro­benzohydrazidato-κ2N′,O](methanol-κO)(methano­lato-κO)oxido­vanadium(V)

Wang, F.-M.

doi:10.1107/S1600536811008774

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m433-m434

doi:10.1107/S1600536811008774

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[N′-(5-Bromo-2-oxidobenzylidene-κO)-2-chlorobenzohydrazidato-κ²N′,O](methanol-κO)(methanolato-κO)oxidovanadium(V)

Fu-Ming Wang ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou Shandong 253023, People's Republic of China
^*Correspondence e-mail: wfm99999@126.com

(Received 1 March 2011; accepted 8 March 2011; online 12 March 2011)

The V^V atom in the title complex, [V(C₁₄H₈BrClN₂O₂)(CH₃O)O(CH₃OH)], is six-coordinated by one phenolate O, one imine N and one enolic O atom of the hydrazone ligand, one oxide O atom, one methanol O atom and one methoxide O atom in a distorted octahedral geometry. The dihedral angle between the two benzene rings of the hydrazone ligand is 13.2 (3)°. The deviation of the V atom towards the oxide O atom from the plane defined by the three donor atoms of the hydrazone ligand and the methoxy O atom is 0.318 (2) Å. Bond lengths are comparable with those observed in similar oxidovanadium(V) complexes with hydrazone ligands. In the crystal, pairs of molecules are linked through intermolecular O—H⋯N hydrogen bonds, forming dimers.

Related literature

For background to hydrazone compounds and their complexes, see: Seena et al. (2008 ); Bastos et al. (2008 ); Sarkar & Pal (2008 ); Nica et al. (2007 ). For similar oxidovanadium(V) complexes, see: Kurup et al. (2010 ); Rajak et al. (2000 ); Grüning et al. (1999 ); Mondal et al. (2009 ).

Experimental

Crystal data

[V(C₁₄H₈BrClN₂O₂)(CH₃O)O(CH₄O)]
M_r = 481.60
Monoclinic, C 2/c
a = 28.09 (2) Å
b = 7.992 (6) Å
c = 20.163 (14) Å
β = 121.854 (7)°
V = 3844 (5) Å³
Z = 8
Mo Kα radiation
μ = 2.76 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.491, T_max = 0.569
9750 measured reflections
4081 independent reflections
2266 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.103
S = 1.02
4081 reflections
240 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—O4	1.582 (3)
V1—O3	1.765 (3)
V1—O1	1.859 (3)
V1—O2	1.957 (3)
V1—N1	2.134 (3)
V1—O5	2.403 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2ⁱ	0.85 (4)	2.06 (4)	2.906 (4)	178 (5)
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008774/qm2003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008774/qm2003Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds and their oxovanadium complexes have received much attention due to their structures and biological properties (Seena et al., 2008; Bastos et al., 2008; Sarkar & Pal, 2008; Nica et al., 2007). In this paper, the title new oxovanadium(V) complex with a hydrazone ligand is reported.

The V^V atom in the title complex, Fig. 1, is six-coordinated by one phenolic O, one imine N, and one enolic O atoms of the hydrazone ligand, by one oxo O atom, and by two O atoms respectively from a methanol molecule and a methoxide ligand, forming a distorted octahedral geometry. The dihedral angle between the two benzene rings of the hydrazone ligand is 13.2 (3)°. The deviation of the V atom from the plane defined by the three donor atoms of the hydrazone ligand and the methoxy O atom towards the oxo O atom is 0.318 (2) Å. The coordinate bond lengths and angles (Table 1) are comparable with those observed in similar oxovanadium(V) complexes (Kurup et al., 2010; Rajak et al., 2000; Grüning et al., 1999; Mondal et al., 2009). In the crystal structure, adjacent two molecules are linked through intermolecular O—H···N hydrogen bonds (Table 2), to form a dimer, as shown in Fig. 2.

Related literature top

For background to hydrazone compounds and their complexes, see: Seena et al. (2008); Bastos et al. (2008); Sarkar & Pal (2008); Nica et al. (2007). For similar oxovanadium(V) complexes, see: Kurup et al. (2010); Rajak et al. (2000); Grüning et al. (1999); Mondal et al. (2009).

Experimental top

5-Bromosalicylaldehyde (1 mmol, 0.20 g), 2-chlorobenzohydrazide 1 mmol, 0.17 g), and VO(acac)₂ (1 mmol, 0.26 g) were mixed in methanol (30 ml). The mixture was boiled under reflux for 2 h, then cooled to room temperature. Brown block-like single crystals, suitable for X-ray diffraction, were formed after slow evaporation of the solution in air for a few days.

Computing details top

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

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular packing of the title complex, viewed along the b axis.

[N'-(5-Bromo-2-oxidobenzylidene-κO)-2- chlorobenzohydrazidato-κ²N',O](methanol- κO)(methanolato-κO)oxidovanadium(V) top

Crystal data top

[V(C₁₄H₈BrClN₂O₂)(CH₃O)O(CH₄O)]	F(000) = 1920
M_r = 481.60	D_x = 1.664 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.09 (2) Å	Cell parameters from 1798 reflections
b = 7.992 (6) Å	θ = 2.3–25.0°
c = 20.163 (14) Å	µ = 2.76 mm⁻¹
β = 121.854 (7)°	T = 298 K
V = 3844 (5) Å³	Block, brown
Z = 8	0.30 × 0.27 × 0.23 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4081 independent reflections
Radiation source: fine-focus sealed tube	2266 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→35
T_min = 0.491, T_max = 0.569	k = −9→9
9750 measured reflections	l = −25→25

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0359P)²] where P = (F_o² + 2F_c²)/3
4081 reflections	(Δ/σ)_max < 0.001
240 parameters	Δρ_max = 0.45 e Å⁻³
1 restraint	Δρ_min = −0.44 e Å⁻³

Crystal data top

[V(C₁₄H₈BrClN₂O₂)(CH₃O)O(CH₄O)]	V = 3844 (5) Å³
M_r = 481.60	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.09 (2) Å	µ = 2.76 mm⁻¹
b = 7.992 (6) Å	T = 298 K
c = 20.163 (14) Å	0.30 × 0.27 × 0.23 mm
β = 121.854 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4081 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2266 reflections with I > 2σ(I)
T_min = 0.491, T_max = 0.569	R_int = 0.056
9750 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.45 e Å⁻³
4081 reflections	Δρ_min = −0.44 e Å⁻³
240 parameters

Special details top

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
V1	0.33992 (3)	0.48966 (10)	0.15964 (4)	0.0355 (2)
Br1	0.05406 (2)	0.13036 (7)	0.00218 (3)	0.05439 (19)
Cl1	0.44356 (6)	0.87745 (17)	0.12452 (7)	0.0663 (4)
H5	0.2799 (16)	0.809 (6)	0.1145 (18)	0.099*
N1	0.27232 (13)	0.5095 (4)	0.04108 (16)	0.0281 (8)
N2	0.28364 (14)	0.5947 (4)	−0.01011 (18)	0.0306 (8)
O1	0.28365 (12)	0.4401 (4)	0.17896 (15)	0.0428 (8)
O2	0.37010 (11)	0.6037 (3)	0.10369 (15)	0.0392 (8)
O3	0.39495 (11)	0.5587 (4)	0.25184 (14)	0.0418 (8)
O4	0.35806 (13)	0.3060 (4)	0.15302 (15)	0.0519 (9)
O5	0.30672 (12)	0.7684 (4)	0.15650 (16)	0.0441 (8)
C1	0.20329 (17)	0.3624 (5)	0.0557 (2)	0.0298 (10)
C2	0.23468 (17)	0.3619 (5)	0.1384 (2)	0.0336 (10)
C3	0.21228 (18)	0.2811 (6)	0.1779 (2)	0.0425 (12)
H3	0.2332	0.2758	0.2321	0.051*
C4	0.15989 (18)	0.2100 (6)	0.1374 (2)	0.0422 (12)
H4	0.1456	0.1574	0.1644	0.051*
C5	0.12819 (16)	0.2159 (5)	0.0566 (2)	0.0351 (11)
C6	0.14949 (17)	0.2896 (5)	0.0161 (2)	0.0346 (11)
H6	0.1281	0.2914	−0.0382	0.042*
C7	0.22241 (18)	0.4472 (5)	0.0110 (2)	0.0331 (10)
H7	0.1975	0.4580	−0.0426	0.040*
C8	0.33695 (17)	0.6358 (5)	0.0297 (2)	0.0309 (10)
C9	0.36154 (17)	0.7211 (5)	−0.0115 (2)	0.0310 (10)
C10	0.40956 (18)	0.8227 (5)	0.0260 (2)	0.0393 (11)
C11	0.43223 (19)	0.8885 (6)	−0.0144 (3)	0.0482 (13)
H11	0.4648	0.9521	0.0118	0.058*
C12	0.4068 (2)	0.8607 (6)	−0.0937 (3)	0.0546 (14)
H12	0.4218	0.9076	−0.1210	0.065*
C13	0.3589 (2)	0.7628 (6)	−0.1326 (3)	0.0530 (13)
H13	0.3420	0.7419	−0.1857	0.064*
C14	0.33694 (17)	0.6971 (5)	−0.0914 (2)	0.0393 (11)
H14	0.3043	0.6340	−0.1180	0.047*
C15	0.44932 (19)	0.4960 (8)	0.3020 (3)	0.0801 (19)
H15A	0.4502	0.3791	0.2918	0.120*
H15B	0.4597	0.5109	0.3552	0.120*
H15C	0.4752	0.5552	0.2932	0.120*
C16	0.3407 (2)	0.9086 (6)	0.1983 (3)	0.0563 (14)
H16A	0.3700	0.8736	0.2494	0.084*
H16B	0.3181	0.9920	0.2030	0.084*
H16C	0.3569	0.9547	0.1706	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0370 (5)	0.0392 (5)	0.0266 (4)	−0.0050 (4)	0.0141 (4)	0.0019 (4)
Br1	0.0345 (3)	0.0605 (4)	0.0636 (3)	−0.0119 (3)	0.0227 (3)	−0.0005 (3)
Cl1	0.0644 (9)	0.0763 (10)	0.0548 (8)	−0.0275 (8)	0.0292 (7)	−0.0141 (7)
N1	0.032 (2)	0.028 (2)	0.0254 (17)	−0.0033 (17)	0.0157 (16)	0.0003 (16)
N2	0.033 (2)	0.032 (2)	0.0292 (18)	−0.0039 (17)	0.0180 (17)	0.0002 (16)
O1	0.0400 (19)	0.058 (2)	0.0281 (15)	−0.0200 (16)	0.0165 (15)	−0.0009 (15)
O2	0.0330 (17)	0.049 (2)	0.0303 (16)	−0.0054 (15)	0.0130 (14)	0.0083 (14)
O3	0.0318 (18)	0.055 (2)	0.0286 (16)	0.0001 (16)	0.0094 (15)	0.0063 (15)
O4	0.067 (2)	0.042 (2)	0.0389 (18)	0.0046 (18)	0.0226 (17)	0.0038 (15)
O5	0.041 (2)	0.038 (2)	0.0410 (18)	−0.0035 (17)	0.0129 (15)	−0.0027 (16)
C1	0.033 (2)	0.028 (3)	0.028 (2)	−0.001 (2)	0.015 (2)	0.0011 (19)
C2	0.033 (3)	0.034 (3)	0.034 (2)	−0.005 (2)	0.018 (2)	0.000 (2)
C3	0.047 (3)	0.053 (3)	0.032 (2)	−0.012 (3)	0.024 (2)	−0.003 (2)
C4	0.045 (3)	0.045 (3)	0.047 (3)	−0.010 (2)	0.031 (3)	0.001 (2)
C5	0.031 (3)	0.036 (3)	0.038 (2)	−0.002 (2)	0.018 (2)	−0.001 (2)
C6	0.037 (3)	0.033 (3)	0.028 (2)	0.000 (2)	0.013 (2)	0.000 (2)
C7	0.034 (3)	0.037 (3)	0.025 (2)	−0.001 (2)	0.013 (2)	0.000 (2)
C8	0.035 (3)	0.031 (3)	0.033 (2)	0.001 (2)	0.022 (2)	0.002 (2)
C9	0.033 (2)	0.025 (3)	0.037 (2)	0.003 (2)	0.019 (2)	0.002 (2)
C10	0.040 (3)	0.034 (3)	0.043 (3)	0.005 (2)	0.021 (2)	0.004 (2)
C11	0.038 (3)	0.048 (3)	0.064 (3)	−0.009 (2)	0.031 (3)	0.000 (3)
C12	0.060 (3)	0.057 (4)	0.070 (4)	0.002 (3)	0.050 (3)	0.015 (3)
C13	0.054 (3)	0.069 (4)	0.046 (3)	0.001 (3)	0.033 (3)	0.009 (3)
C14	0.032 (3)	0.048 (3)	0.039 (3)	0.005 (2)	0.020 (2)	0.004 (2)
C15	0.039 (3)	0.116 (5)	0.058 (3)	0.015 (4)	0.007 (3)	0.007 (4)
C16	0.066 (4)	0.053 (4)	0.043 (3)	−0.013 (3)	0.024 (3)	−0.007 (3)

Geometric parameters (Å, º) top

V1—O4	1.582 (3)	C4—C5	1.384 (5)
V1—O3	1.765 (3)	C4—H4	0.9300
V1—O1	1.859 (3)	C5—C6	1.374 (5)
V1—O2	1.957 (3)	C6—H6	0.9300
V1—N1	2.134 (3)	C7—H7	0.9300
V1—O5	2.403 (4)	C8—C9	1.496 (5)
Br1—C5	1.896 (4)	C9—C14	1.390 (5)
Cl1—C10	1.746 (4)	C9—C10	1.405 (6)
N1—C7	1.298 (5)	C10—C11	1.375 (6)
N1—N2	1.406 (4)	C11—C12	1.383 (6)
N2—C8	1.314 (5)	C11—H11	0.9300
O1—C2	1.328 (5)	C12—C13	1.386 (6)
O2—C8	1.301 (4)	C12—H12	0.9300
O3—C15	1.406 (5)	C13—C14	1.375 (5)
O5—C16	1.424 (5)	C13—H13	0.9300
O5—H5	0.85 (4)	C14—H14	0.9300
C1—C6	1.409 (5)	C15—H15A	0.9600
C1—C2	1.418 (5)	C15—H15B	0.9600
C1—C7	1.439 (5)	C15—H15C	0.9600
C2—C3	1.404 (5)	C16—H16A	0.9600
C3—C4	1.374 (5)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600

O4—V1—O3	103.70 (15)	C5—C6—C1	120.9 (4)
O4—V1—O1	99.61 (15)	C5—C6—H6	119.6
O3—V1—O1	102.39 (13)	C1—C6—H6	119.6
O4—V1—O2	97.29 (14)	N1—C7—C1	123.8 (4)
O3—V1—O2	93.25 (13)	N1—C7—H7	118.1
O1—V1—O2	153.46 (12)	C1—C7—H7	118.1
O4—V1—N1	96.33 (13)	O2—C8—N2	123.2 (3)
O3—V1—N1	157.41 (14)	O2—C8—C9	117.8 (4)
O1—V1—N1	84.17 (13)	N2—C8—C9	119.1 (4)
O2—V1—N1	73.72 (13)	C14—C9—C10	116.9 (4)
O4—V1—O5	174.59 (12)	C14—C9—C8	119.2 (4)
O3—V1—O5	81.36 (12)	C10—C9—C8	123.9 (4)
O1—V1—O5	80.92 (13)	C11—C10—C9	121.1 (4)
O2—V1—O5	80.39 (12)	C11—C10—Cl1	115.6 (4)
N1—V1—O5	78.35 (11)	C9—C10—Cl1	123.4 (3)
C7—N1—N2	116.7 (3)	C10—C11—C12	120.4 (4)
C7—N1—V1	126.8 (3)	C10—C11—H11	119.8
N2—N1—V1	116.5 (2)	C12—C11—H11	119.8
C8—N2—N1	107.4 (3)	C11—C12—C13	119.9 (4)
C2—O1—V1	133.7 (3)	C11—C12—H12	120.0
C8—O2—V1	119.2 (2)	C13—C12—H12	120.0
C15—O3—V1	131.4 (3)	C14—C13—C12	119.0 (4)
C16—O5—V1	125.8 (3)	C14—C13—H13	120.5
C16—O5—H5	105 (4)	C12—C13—H13	120.5
V1—O5—H5	121 (4)	C13—C14—C9	122.7 (4)
C6—C1—C2	118.7 (4)	C13—C14—H14	118.7
C6—C1—C7	118.8 (3)	C9—C14—H14	118.7
C2—C1—C7	122.2 (4)	O3—C15—H15A	109.5
O1—C2—C3	119.7 (4)	O3—C15—H15B	109.5
O1—C2—C1	121.4 (3)	H15A—C15—H15B	109.5
C3—C2—C1	118.8 (4)	O3—C15—H15C	109.5
C4—C3—C2	120.9 (4)	H15A—C15—H15C	109.5
C4—C3—H3	119.6	H15B—C15—H15C	109.5
C2—C3—H3	119.6	O5—C16—H16A	109.5
C3—C4—C5	120.5 (4)	O5—C16—H16B	109.5
C3—C4—H4	119.8	H16A—C16—H16B	109.5
C5—C4—H4	119.8	O5—C16—H16C	109.5
C6—C5—C4	120.2 (4)	H16A—C16—H16C	109.5
C6—C5—Br1	120.0 (3)	H16B—C16—H16C	109.5
C4—C5—Br1	119.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2ⁱ	0.85 (4)	2.06 (4)	2.906 (4)	178 (5)

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

Experimental details

Crystal data
Chemical formula	[V(C₁₄H₈BrClN₂O₂)(CH₃O)O(CH₄O)]
M_r	481.60
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	28.09 (2), 7.992 (6), 20.163 (14)
β (°)	121.854 (7)
V (Å³)	3844 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.76
Crystal size (mm)	0.30 × 0.27 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.491, 0.569
No. of measured, independent and observed [I > 2σ(I)] reflections	9750, 4081, 2266
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.103, 1.02
No. of reflections	4081
No. of parameters	240
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.44

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

V1—O4	1.582 (3)	V1—O2	1.957 (3)
V1—O3	1.765 (3)	V1—N1	2.134 (3)
V1—O1	1.859 (3)	V1—O5	2.403 (4)

O4—V1—O3	103.70 (15)	O1—V1—N1	84.17 (13)
O4—V1—O1	99.61 (15)	O2—V1—N1	73.72 (13)
O3—V1—O1	102.39 (13)	O4—V1—O5	174.59 (12)
O4—V1—O2	97.29 (14)	O3—V1—O5	81.36 (12)
O3—V1—O2	93.25 (13)	O1—V1—O5	80.92 (13)
O1—V1—O2	153.46 (12)	O2—V1—O5	80.39 (12)
O4—V1—N1	96.33 (13)	N1—V1—O5	78.35 (11)
O3—V1—N1	157.41 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2ⁱ	0.85 (4)	2.06 (4)	2.906 (4)	178 (5)

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

Acknowledgements

This work was supported financially by Dezhou University, People's Republic of China.

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