Tris(ethyl­enediamine)cobalt(II) sulfate

Yotnoi, B.; Seeharaj, A.; Chimupala, Y.; Rujiwatra, A.

doi:10.1107/S1600536810016168

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page m628

https://doi.org/10.1107/S1600536810016168

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Tris(ethylenediamine)cobalt(II) sulfate

Bunlawee Yotnoi,^a Athittaya Seeharaj,^a Yothin Chimupala ^a and Apinpus Rujiwatra ^a ^*

^aDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
^*Correspondence e-mail: apinpus@gmail.com

(Received 27 April 2010; accepted 3 May 2010; online 8 May 2010)

The structure of the title compound, [Co^II(C₂H₈N₂)₃]SO₄, the cobalt example of [M(C₂H₈N₂)₃]SO₄, is reported. The Co and S atoms are located at the 2d and 2c Wyckoff sites (point symmetry 32), respectively. The Co atom is coordinated by six N atoms of three chelating ethylenediamine molecules generated from half of the ethylenediamine molecule in the asymmetric unit. The O atoms of the sulfate anion are disordered mostly over two crystallographic sites. The third disorder site of O (site symmetry 3) has a site occupancy approaching zero. The H atoms of the ethylenediamine molecules interact with the sulfate anions via intermolecular N—H⋯O hydrogen-bonding interactions.

Related literature

For isostructural [M(C₂H₈N₂)₃]SO₄ complexes, see: Haque et al. (1970 ); Cullen & Lingafelter (1970 ); Daniels et al. (1995 ); Lu (2009 ) for the nickel, copper, vanadium and manganese analogues, respectively.

Experimental

Crystal data

[Co(C₂H₈N₂)₃]SO₄
M_r = 335.30
Trigonal, $[P \overline 31c ]$
a = 8.9920 (2) Å
c = 9.5927 (3) Å
V = 671.71 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.45 mm⁻¹
T = 298 K
0.48 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.543, T_max = 0.760
3638 measured reflections
688 independent reflections
589 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.069
S = 1.06
688 reflections
47 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.90	2.13	2.889 (12)	142
N1—H1A⋯O1ⁱ	0.90	2.15	3.049 (7)	176
N1—H1A⋯O2ⁱⁱ	0.90	2.22	3.054 (8)	155
N1—H1A⋯O2ⁱⁱⁱ	0.90	2.32	3.104 (11)	145
N1—H1B⋯O2^iv	0.90	1.98	2.843 (6)	161
N1—H1B⋯O1	0.90	2.48	3.353 (14)	165
N1—H1B⋯O1^v	0.90	2.52	3.256 (10)	139
Symmetry codes: (i) -x+1, -y+1, -z; (ii) y, -x+y, -z; (iii) x-y+1, x, -z; (iv) -x+y, -x+1, z; (v) $[-y+1, -x+1, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ) and WinGX (Farrugia, 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810016168/tk2667sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016168/tk2667Isup2.hkl

checkCIF report

Comment top

The title complex, [Co^II(C₂H₈N₂)₃]SO₄ (Fig. 1), is isostructural to the earlier reported [Ni^II(C₂H₈N₂)₃]SO₄ (Haque et al.,, 1970), [V^II(C₂H₈N₂)₃]SO₄ (Daniels et al., 1995), [Mn^II(C₂H₈N₂)₃]SO₄ (Lu, 2009) and [Cu^II(C₂H₈N₂)₃]SO₄ (Cullen & Lingafelter, 1970) complexes, constituting the [M^II(C₂H₂N₂)₃]SO₄ series. The [M^II(C₂H₂N₂)₃]SO₄ structures crystallize in the same trigonal space group of P31c with quite similar cell parameters. Likewise, the metal and sulfur atoms are positioned in the same crystallographic sites; M^II on the 2d and S on the 2c Wyckoff sites (each with point symmetry 32). The disorder about the six-fold rotation axis found in the sulfate anion is intriguingly common in each structure, although the number of unique O atoms varies from two to four. In the structure of [Co^II(C₂H₈N₂)₃]SO₄, the O atoms were refined as being disordered over three crystallographic sites, although the site occupancy of O3 located on the 4f Wyckoff site approaches zero. The bond length associated with this O3 atom (S1—O3; 1.382 (16) Å) is notably shorter than the other S—O bonds (1.431 (5)–1.445 (5) Å). The disordered sulfate anions are linked to the [Co^II(C₂H₈N₂)₃]²⁺ cations by hydrogen bonding interactions of N—H···O type to form a hydrogen-bonding supramolecular network. The hydrogen bonding geometries are consistent with those of the previously reported [M^II(C₂H₂N₂)₃]SO₄ complexes.

Related literature top

For isostructural [M(C₂H₈N₂)₃]SO₄ complexes, see: Haque et al. (1970); Cullen & Lingafelter (1970); Daniels et al. (1995); Lu (2009) for the nickel, copper, vanadium and manganese analogues, respectively.

Experimental top

Orange blocks of the title complex were synthesized and grown from the sovolthermal reaction of Co(NO₃)₂.6H₂O (1.34 mmol), NH₂SO₃H (1.34 mmol), NH₂C₂H₄NH₂ (3.89 mmol) in ethylene glycol (160 mmol), conducted at 453 K for 72 h.

Structure description top

For isostructural [M(C₂H₈N₂)₃]SO₄ complexes, see: Haque et al. (1970); Cullen & Lingafelter (1970); Daniels et al. (1995); Lu (2009) for the nickel, copper, vanadium and manganese analogues, respectively.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of the title complex showing atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. [Symmetry codes: (i) -y+1, x-y, z; (ii) -x+y+1, -x+1, z; (iii) -y+1, -x+1, -z+1/2; (iv) -x+y+1, y, -z+1/2; (v) x, x-y, -z+1/2; (vi) -y+1, x-y+1, z, (vii) -x+y, -x+1, z; (viii) -x+y, y, -z+1/2; (ix) x, x-y+1, -z+1/2]. Hydrogen atoms are omitted.
	Fig. 2. View of the hydrogen bonding interactions (dotted lines) between the disordered sulfate O atoms and the amino-H atoms of the [Co^II(C₂H₈N₂)]²⁺ cations. [Symmetry codes: (ii) -x+y+1, -x+1, z; (iii) -y+1, -x+1, -z+1/2; (viii) -x+y, y, -z+1/2; (ix) x, x-y+1, -z+1/2; (xiii) y, x, z+1/2; (xiv) -y+x, -y+1, -z+1/2; (xv) -x+1, -x+y+1, z+1/2].

Tris(ethylenediamine)cobalt(II) sulfate top

Crystal data top

[Co(C₂H₈N₂)₃]SO₄	D_x = 1.658 Mg m⁻³
M_r = 335.30	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31c	Cell parameters from 589 reflections
Hall symbol: -P 3 2c	θ = 2.6–31.0°
a = 8.9920 (2) Å	µ = 1.45 mm⁻¹
c = 9.5927 (3) Å	T = 298 K
V = 671.71 (3) Å³	Block, orange
Z = 2	0.48 × 0.22 × 0.20 mm
F(000) = 354

Data collection top

Bruker SMART CCD area-detector diffractometer	688 independent reflections
Radiation source: fine-focus sealed tube	589 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
? scan	θ_max = 31.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
T_min = 0.543, T_max = 0.760	k = −11→11
3638 measured reflections	l = −11→13

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0354P)² + 0.1217P] where P = (F_o² + 2F_c²)/3
688 reflections	(Δ/σ)_max < 0.001
47 parameters	Δρ_max = 0.25 e Å⁻³
16 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Co(C₂H₈N₂)₃]SO₄	Z = 2
M_r = 335.30	Mo Kα radiation
Trigonal, P31c	µ = 1.45 mm⁻¹
a = 8.9920 (2) Å	T = 298 K
c = 9.5927 (3) Å	0.48 × 0.22 × 0.20 mm
V = 671.71 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	688 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	589 reflections with I > 2σ(I)
T_min = 0.543, T_max = 0.760	R_int = 0.027
3638 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	16 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.06	Δρ_max = 0.25 e Å⁻³
688 reflections	Δρ_min = −0.29 e Å⁻³
47 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 > 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	Occ. (<1)
Co1	0.6667	0.3333	0.2500	0.02175 (16)
N1	0.68784 (18)	0.54599 (18)	0.12760 (13)	0.0332 (3)
H1A	0.6936	0.5265	0.0363	0.040*
H1B	0.5954	0.5579	0.1418	0.040*
S1	0.3333	0.6667	0.2500	0.0240 (2)
C1	0.8446 (2)	0.7024 (2)	0.17145 (19)	0.0388 (4)
H1C	0.8405	0.8031	0.1409	0.047*
H1D	0.9444	0.7056	0.1297	0.047*
O1	0.3029 (19)	0.5088 (9)	0.1852 (8)	0.096 (3)	0.319 (8)
O2	0.339 (2)	0.7851 (9)	0.1475 (6)	0.096 (4)	0.316 (9)
O3	0.3333	0.6667	0.1059 (16)	0.086 (8)	0.094 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0226 (2)	0.0226 (2)	0.0201 (2)	0.01129 (10)	0.000	0.000
N1	0.0410 (8)	0.0330 (7)	0.0283 (7)	0.0204 (6)	−0.0033 (5)	0.0031 (5)
S1	0.0243 (3)	0.0243 (3)	0.0233 (4)	0.01215 (14)	0.000	0.000
C1	0.0445 (10)	0.0267 (8)	0.0413 (9)	0.0147 (7)	0.0058 (7)	0.0076 (6)
O1	0.185 (9)	0.051 (4)	0.063 (4)	0.069 (5)	−0.012 (5)	−0.016 (3)
O2	0.194 (12)	0.055 (4)	0.044 (3)	0.067 (5)	−0.012 (4)	0.012 (3)
O3	0.118 (11)	0.118 (11)	0.021 (11)	0.059 (5)	0.000	0.000

Geometric parameters (Å, º) top

Co1—N1ⁱ	2.1696 (13)	S1—O2^vi	1.431 (5)
Co1—N1ⁱⁱ	2.1696 (13)	S1—O2^v	1.431 (5)
Co1—N1ⁱⁱⁱ	2.1696 (13)	S1—O2^vii	1.431 (5)
Co1—N1^iv	2.1696 (13)	S1—O2^viii	1.431 (5)
Co1—N1	2.1696 (13)	S1—O2^ix	1.431 (5)
Co1—N1^v	2.1696 (13)	S1—O1^ix	1.445 (5)
N1—C1	1.469 (2)	S1—O1^viii	1.445 (5)
N1—H1A	0.9000	S1—O1^vi	1.445 (5)
N1—H1B	0.9000	S1—O1^vii	1.445 (5)
S1—O3	1.382 (16)	C1—C1^iv	1.512 (4)
S1—O3^v	1.382 (16)	C1—H1C	0.9700
S1—O2	1.431 (5)	C1—H1D	0.9700

N1ⁱ—Co1—N1ⁱⁱ	80.49 (7)	O2^viii—S1—O1^viii	110.7 (4)
N1ⁱ—Co1—N1ⁱⁱⁱ	93.48 (5)	O2^ix—S1—O1^viii	138.0 (11)
N1ⁱⁱ—Co1—N1ⁱⁱⁱ	93.17 (8)	O1^ix—S1—O1^viii	63.4 (8)
N1ⁱ—Co1—N1^iv	93.17 (8)	O3—S1—O1^vi	64.5 (3)
N1ⁱⁱ—Co1—N1^iv	93.48 (5)	O3^v—S1—O1^vi	115.5 (3)
N1ⁱⁱⁱ—Co1—N1^iv	171.28 (7)	O2—S1—O1^vi	57.2 (5)
N1ⁱ—Co1—N1	93.48 (5)	O2^vi—S1—O1^vi	110.7 (4)
N1ⁱⁱ—Co1—N1	171.28 (8)	O2^v—S1—O1^vi	138.0 (11)
N1ⁱⁱⁱ—Co1—N1	93.48 (5)	O2^vii—S1—O1^vi	69.9 (6)
N1^iv—Co1—N1	80.49 (7)	O2^viii—S1—O1^vi	45.7 (4)
N1ⁱ—Co1—N1^v	171.28 (8)	O2^ix—S1—O1^vi	119.2 (10)
N1ⁱⁱ—Co1—N1^v	93.48 (5)	O1^ix—S1—O1^vi	93.3 (11)
N1ⁱⁱⁱ—Co1—N1^v	80.49 (7)	O1^viii—S1—O1^vi	102.9 (4)
N1^iv—Co1—N1^v	93.48 (5)	O3—S1—O1^vii	115.5 (3)
N1—Co1—N1^v	93.17 (8)	O3^v—S1—O1^vii	64.5 (3)
C1—N1—Co1	107.94 (10)	O2—S1—O1^vii	138.0 (11)
C1—N1—H1A	110.1	O2^vi—S1—O1^vii	69.9 (6)
Co1—N1—H1A	110.1	O2^v—S1—O1^vii	57.2 (5)
C1—N1—H1B	110.1	O2^vii—S1—O1^vii	110.7 (4)
Co1—N1—H1B	110.1	O2^viii—S1—O1^vii	119.2 (10)
H1A—N1—H1B	108.4	O2^ix—S1—O1^vii	45.7 (4)
O3—S1—O3^v	180.000 (3)	O1^ix—S1—O1^vii	102.9 (4)
O3—S1—O2	46.6 (3)	O1^viii—S1—O1^vii	93.3 (11)
O3^v—S1—O2	133.4 (3)	O1^vi—S1—O1^vii	161.1 (12)
O3—S1—O2^vi	46.6 (3)	N1—C1—C1^iv	108.84 (12)
O3^v—S1—O2^vi	133.4 (3)	N1—C1—H1C	109.9
O2—S1—O2^vi	78.0 (5)	C1^iv—C1—H1C	109.9
O3—S1—O2^v	133.4 (3)	N1—C1—H1D	109.9
O3^v—S1—O2^v	46.6 (3)	C1^iv—C1—H1D	109.9
O2—S1—O2^v	104.4 (11)	H1C—C1—H1D	108.3
O2^vi—S1—O2^v	99.7 (7)	O2^vi—O1—O2^viii	91.9 (8)
O3—S1—O2^vii	133.4 (3)	O2^vi—O1—S1	66.5 (5)
O3^v—S1—O2^vii	46.6 (3)	O2^viii—O1—S1	60.9 (3)
O2—S1—O2^vii	99.7 (7)	O2^vi—O1—O1^vii	75.7 (11)
O2^vi—S1—O2^vii	176.3 (13)	O2^viii—O1—O1^vii	117.8 (4)
O2^v—S1—O2^vii	78.0 (5)	S1—O1—O1^vii	58.3 (4)
O3—S1—O2^viii	46.6 (3)	O2^vi—O1—O2^ix	108.3 (7)
O3^v—S1—O2^viii	133.4 (3)	O2^viii—O1—O2^ix	92.2 (8)
O2—S1—O2^viii	78.0 (5)	S1—O1—O2^ix	54.6 (4)
O2^vi—S1—O2^viii	78.0 (5)	O1^viii—O2—O1^vi	129.8 (7)
O2^v—S1—O2^viii	176.3 (13)	O1^viii—O2—S1	67.8 (4)
O2^vii—S1—O2^viii	104.4 (11)	O1^vi—O2—S1	61.9 (4)
O3—S1—O2^ix	133.4 (3)	O1^viii—O2—O1^ix	63.3 (12)
O3^v—S1—O2^ix	46.6 (3)	O1^vi—O2—O1^ix	87.5 (9)
O2—S1—O2^ix	176.3 (13)	S1—O2—O1^ix	55.5 (3)
O2^vi—S1—O2^ix	104.4 (11)	O1^viii—O2—O2^vi	49.8 (6)
O2^v—S1—O2^ix	78.0 (5)	O1^vi—O2—O2^vi	95.3 (5)
O2^vii—S1—O2^ix	78.0 (5)	S1—O2—O2^vi	51.0 (2)
O2^viii—S1—O2^ix	99.7 (7)	O1^ix—O2—O2^vi	91.9 (8)
O3—S1—O1^ix	115.5 (3)	O1^viii—O2—O2^viii	106.1 (5)
O3^v—S1—O1^ix	64.5 (3)	S1—O2—O2^viii	51.0 (2)
O2—S1—O1^ix	69.9 (6)	O1^ix—O2—O2^viii	102.2 (4)
O2^vi—S1—O1^ix	119.2 (10)	O2^vi—O2—O2^viii	60.000 (1)
O2^v—S1—O1^ix	45.7 (4)	O2^vi—O3—O2^viii	107.9 (8)
O2^vii—S1—O1^ix	57.2 (5)	O2^vi—O3—S1	69.0 (8)
O2^viii—S1—O1^ix	138.0 (11)	O2^viii—O3—S1	69.0 (8)
O2^ix—S1—O1^ix	110.7 (4)	O2^vi—O3—O1^viii	61.1 (6)
O3—S1—O1^viii	64.5 (3)	O2^viii—O3—O1^viii	128.2 (13)
O3^v—S1—O1^viii	115.5 (3)	S1—O3—O1^viii	59.8 (5)
O2—S1—O1^viii	45.7 (4)	O2^vi—O3—O1^vi	128.2 (13)
O2^vi—S1—O1^viii	57.2 (5)	O2^viii—O3—O1^vi	47.4 (6)
O2^v—S1—O1^viii	69.9 (6)	S1—O3—O1^vi	59.8 (5)
O2^vii—S1—O1^viii	119.2 (10)	O1^viii—O3—O1^vi	96.9 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^x	0.90	2.13	2.889 (12)	142
N1—H1A···O1^x	0.90	2.15	3.049 (7)	176
N1—H1A···O2^xi	0.90	2.22	3.054 (8)	155
N1—H1A···O2^xii	0.90	2.32	3.104 (11)	145
N1—H1B···O2^viii	0.90	1.98	2.843 (6)	161
N1—H1B···O1	0.90	2.48	3.353 (14)	165
N1—H1B···O1^v	0.90	2.52	3.256 (10)	139

Symmetry codes: (v) −y+1, −x+1, −z+1/2; (viii) −x+y, −x+1, z; (x) −x+1, −y+1, −z; (xi) y, −x+y, −z; (xii) x−y+1, x, −z.

Experimental details

Crystal data
Chemical formula	[Co(C₂H₈N₂)₃]SO₄
M_r	335.30
Crystal system, space group	Trigonal, P31c
Temperature (K)	298
a, c (Å)	8.9920 (2), 9.5927 (3)
V (Å³)	671.71 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.45
Crystal size (mm)	0.48 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.543, 0.760
No. of measured, independent and observed [I > 2σ(I)] reflections	3638, 688, 589
R_int	0.027

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.069, 1.06
No. of reflections	688
No. of parameters	47
No. of restraints	16
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.29

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008) and WinGX (Farrugia, 1999), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.90	2.13	2.889 (12)	142
N1—H1A···O1ⁱ	0.90	2.15	3.049 (7)	176
N1—H1A···O2ⁱⁱ	0.90	2.22	3.054 (8)	155
N1—H1A···O2ⁱⁱⁱ	0.90	2.32	3.104 (11)	145
N1—H1B···O2^iv	0.90	1.98	2.843 (6)	161
N1—H1B···O1	0.90	2.48	3.353 (14)	165
N1—H1B···O1^v	0.90	2.52	3.256 (10)	139

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

Acknowledgements

This work was supported financially by the Thailand Research Fund and the Center of Excellence for Innovation in Chemistry. BY thanks the Royal Golden Jubilee PhD program and the Graduate School of Chiang Mai University for a graduate scholarship.

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