2-(2,6-Dichloro­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide

Nayak, P.S.; Narayana, B.; Yathirajan, H.S.; Jasinski, J.P.; Butcher, R.J.

doi:10.1107/S1600536813006260

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o523

doi:10.1107/S1600536813006260

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2-(2,6-Dichlorophenyl)-N-(1,3-thiazol-2-yl)acetamide

Prakash S. Nayak,^a B. Narayana,^a H. S. Yathirajan,^b Jerry P. Jasinski ^c ^* and Ray J. Butcher ^d

^aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: jjasinski@keene.edu

(Received 4 March 2013; accepted 5 March 2013; online 9 March 2013)

In the title compound, C₁₁H₈Cl₂N₂OS, the mean plane of the dichlorophenyl ring is twisted by 79.7 (7)° from that of the thiazole ring. In the crystal, molecules are linked via pairs of N—H⋯N hydrogen bonds, forming inversion dimers which stack along the a-axis direction.

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006 ); Mijin et al. (2008 ). For the coordination abilities of amides, see: Wu et al. (2008 , 2010 ). For related structures, see: Fun et al. (2012a ,b ,c ,d ,e ); Butcher et al. (2013a ,b ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₈Cl₂N₂OS
M_r = 287.15
Triclinic, $[P \overline 1]$
a = 7.1278 (4) Å
b = 8.4434 (4) Å
c = 10.3637 (6) Å
α = 95.341 (4)°
β = 106.140 (5)°
γ = 96.745 (4)°
V = 589.80 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 123 K
0.3 × 0.2 × 0.1 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012 ) T_min = 0.909, T_max = 1.000
10674 measured reflections
5881 independent reflections
4481 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.096
S = 1.05
5881 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2ⁱ	0.890 (19)	2.030 (19)	2.9165 (14)	173.9 (17)
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536813006260/hg5297sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006260/hg5297Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006260/hg5297Isup3.cml

checkCIF report

Comment top

N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2006, 2008). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008, 2010). Crystal structures of some acetamide derivatives viz., (2,2-diphenyl-N-(1,3-thiazol-2-yl)acetamide, 2-(4-chlorophenyl)-N-(1,3-thiazol-2-yl)acetamide, 2-(naphthalen-1-yl)-N-(1,3-thiazol-2-yl)acetamide, N-(1,3-thiazol-2-yl)-2-(2,4,6-trimethyl phenyl)acetamide, 2-(2-fluorophenyl)-N-(1,3-thiazol-2-yl)acetamide (Fun et al., 2012a,b,c,d,e), 2-(2,6-dichlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro- 1H-pyrazol-4-yl)acetamide, 2-(2,4-Dichlorophenyl)-N-(1,5-dimethyl-3-oxo- 2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide (Butcher et al., 2013a,b) have been reported. In view of the importance of amides, we report herein the crystal structure of the title compound, C₁₁H₈Cl₂N₂OS, (I).

In (I), the mean plane of the dichlorophenyl ring is twisted by 79.7 (7)° from that of the thiazol ring (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987) In the crystal, intermolecular N—H···N hydrogen bonds forming a R2,2(8) graph-set orientation are observed (Table 1) which form infinite 1-D chains along [100] and add to packing stability (Fig. 2).

Related literature top

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006); Mijin et al. (2008). For the coordination abilities of amides, see: Wu et al. (2008, 2010). For related structures, see: Fun et al. (2012a,b,c,d,e); Butcher et al. (2013a,b). For standard bond lengths, see: Allen et al. (1987).

Experimental top

2,6-Dichlorophenylacetic acid (0.240 g, 1 mmol) and 2-aminothiazole (0.1 g, 1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) and were dissolved in dichloromethane (20 mL). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which was extracted thrice with dichloromethane (Fig. 3). The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Single crystals were grown from methanol and acetone mixture (1:1) by the slow evaporation method (M.P.: 489–491K).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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. Molecular structure of the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the a axis. Dashed lines indicate N—H···N intermolecular hydrogen bonds which form chains along [100]. H atoms not involved in hydrogen bonding have been removed for clarity.
	Fig. 3. Reaction scheme.

2-(2,6-Dichlorophenyl)-N-(1,3-thiazol-2-yl)acetamide top

Crystal data top

C₁₁H₈Cl₂N₂OS	Z = 2
M_r = 287.15	F(000) = 292
Triclinic, P1	D_x = 1.617 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1278 (4) Å	Cell parameters from 3814 reflections
b = 8.4434 (4) Å	θ = 3.1–37.5°
c = 10.3637 (6) Å	µ = 0.71 mm⁻¹
α = 95.341 (4)°	T = 123 K
β = 106.140 (5)°	Prism, colorless
γ = 96.745 (4)°	0.3 × 0.2 × 0.1 mm
V = 589.80 (6) Å³

Data collection top

Agilent Xcalibur (Ruby, Gemini) diffractometer	5881 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4481 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 10.5081 pixels mm^-1	θ_max = 37.6°, θ_min = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	k = −13→14
T_min = 0.909, T_max = 1.000	l = −17→8
10674 measured 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0399P)² + 0.0356P] where P = (F_o² + 2F_c²)/3
5881 reflections	(Δ/σ)_max = 0.001
159 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₁H₈Cl₂N₂OS	γ = 96.745 (4)°
M_r = 287.15	V = 589.80 (6) Å³
Triclinic, P1	Z = 2
a = 7.1278 (4) Å	Mo Kα radiation
b = 8.4434 (4) Å	µ = 0.71 mm⁻¹
c = 10.3637 (6) Å	T = 123 K
α = 95.341 (4)°	0.3 × 0.2 × 0.1 mm
β = 106.140 (5)°

Data collection top

Agilent Xcalibur (Ruby, Gemini) diffractometer	5881 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	4481 reflections with I > 2σ(I)
T_min = 0.909, T_max = 1.000	R_int = 0.025
10674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.63 e Å⁻³
5881 reflections	Δρ_min = −0.30 e Å⁻³
159 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
S1	0.07341 (5)	0.70227 (3)	0.53736 (3)	0.01622 (7)
Cl1	0.33730 (6)	0.82751 (4)	0.07966 (4)	0.02553 (8)
Cl2	0.41255 (5)	0.22491 (3)	0.21194 (3)	0.02086 (7)
O1	0.23281 (15)	0.51841 (10)	0.38090 (10)	0.02131 (19)
N1	0.38161 (16)	0.77833 (11)	0.43229 (10)	0.01460 (18)
H1N	0.472 (3)	0.854 (2)	0.4214 (18)	0.033 (5)*
N2	0.30837 (16)	0.97170 (11)	0.58210 (10)	0.01568 (18)
C1	0.36862 (17)	0.52292 (13)	0.13841 (11)	0.01338 (19)
C2	0.29093 (19)	0.61876 (14)	0.03922 (13)	0.0166 (2)
C3	0.1754 (2)	0.55517 (16)	−0.09107 (13)	0.0203 (2)
H3A	0.1266	0.6242	−0.1559	0.024*
C4	0.1326 (2)	0.38945 (16)	−0.12497 (13)	0.0203 (2)
H4A	0.0532	0.3444	−0.2135	0.024*
C5	0.20517 (19)	0.28927 (14)	−0.03037 (13)	0.0183 (2)
H5A	0.1757	0.1757	−0.0536	0.022*
C6	0.32131 (18)	0.35632 (13)	0.09860 (12)	0.0146 (2)
C7	0.49054 (18)	0.59521 (14)	0.28024 (12)	0.0154 (2)
H7A	0.5705	0.6980	0.2768	0.019*
H7B	0.5820	0.5211	0.3199	0.019*
C8	0.35693 (18)	0.62512 (13)	0.36893 (12)	0.0147 (2)
C9	0.26992 (17)	0.82641 (13)	0.51500 (11)	0.01340 (19)
C10	0.1753 (2)	0.98851 (14)	0.65603 (13)	0.0184 (2)
H10A	0.1797	1.0856	0.7118	0.022*
C11	0.0385 (2)	0.85772 (14)	0.64385 (13)	0.0184 (2)
H11B	−0.0622	0.8526	0.6878	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01826 (14)	0.01396 (12)	0.01733 (13)	−0.00207 (9)	0.00928 (11)	−0.00039 (10)
Cl1	0.03479 (19)	0.01430 (12)	0.03140 (17)	0.00564 (11)	0.01460 (14)	0.00504 (11)
Cl2	0.02711 (16)	0.01518 (12)	0.02042 (14)	0.00524 (10)	0.00606 (12)	0.00315 (10)
O1	0.0265 (5)	0.0151 (4)	0.0240 (5)	−0.0047 (3)	0.0152 (4)	−0.0035 (3)
N1	0.0184 (5)	0.0107 (4)	0.0159 (4)	−0.0013 (3)	0.0095 (4)	−0.0019 (3)
N2	0.0189 (5)	0.0130 (4)	0.0161 (4)	0.0000 (3)	0.0088 (4)	−0.0014 (3)
C1	0.0147 (5)	0.0136 (4)	0.0131 (5)	0.0019 (4)	0.0070 (4)	−0.0008 (4)
C2	0.0195 (5)	0.0148 (5)	0.0193 (5)	0.0043 (4)	0.0108 (4)	0.0030 (4)
C3	0.0222 (6)	0.0264 (6)	0.0160 (5)	0.0085 (5)	0.0089 (5)	0.0054 (5)
C4	0.0175 (6)	0.0291 (6)	0.0136 (5)	0.0053 (5)	0.0045 (4)	−0.0025 (4)
C5	0.0182 (5)	0.0178 (5)	0.0176 (5)	0.0020 (4)	0.0055 (4)	−0.0044 (4)
C6	0.0157 (5)	0.0141 (4)	0.0145 (5)	0.0027 (4)	0.0058 (4)	−0.0002 (4)
C7	0.0160 (5)	0.0153 (5)	0.0148 (5)	−0.0007 (4)	0.0068 (4)	−0.0029 (4)
C8	0.0171 (5)	0.0136 (4)	0.0132 (5)	0.0005 (4)	0.0057 (4)	−0.0014 (4)
C9	0.0157 (5)	0.0124 (4)	0.0127 (4)	0.0008 (4)	0.0060 (4)	0.0007 (4)
C10	0.0230 (6)	0.0153 (5)	0.0196 (5)	0.0024 (4)	0.0117 (5)	−0.0009 (4)
C11	0.0200 (6)	0.0192 (5)	0.0190 (5)	0.0018 (4)	0.0119 (5)	0.0001 (4)

Geometric parameters (Å, º) top

S1—C11	1.7212 (13)	C2—C3	1.3901 (18)
S1—C9	1.7306 (11)	C3—C4	1.3867 (19)
Cl1—C2	1.7436 (12)	C3—H3A	0.9500
Cl2—C6	1.7382 (12)	C4—C5	1.3854 (18)
O1—C8	1.2266 (14)	C4—H4A	0.9500
N1—C8	1.3637 (14)	C5—C6	1.3879 (17)
N1—C9	1.3870 (15)	C5—H5A	0.9500
N1—H1N	0.890 (19)	C7—C8	1.5217 (17)
N2—C9	1.3114 (14)	C7—H7A	0.9900
N2—C10	1.3863 (16)	C7—H7B	0.9900
C1—C2	1.4006 (16)	C10—C11	1.3562 (17)
C1—C6	1.4021 (15)	C10—H10A	0.9500
C1—C7	1.5121 (16)	C11—H11B	0.9500

C11—S1—C9	88.83 (6)	C5—C6—Cl2	117.37 (9)
C8—N1—C9	123.21 (10)	C1—C6—Cl2	119.94 (9)
C8—N1—H1N	120.7 (12)	C1—C7—C8	110.36 (10)
C9—N1—H1N	116.1 (12)	C1—C7—H7A	109.6
C9—N2—C10	109.52 (10)	C8—C7—H7A	109.6
C2—C1—C6	115.65 (11)	C1—C7—H7B	109.6
C2—C1—C7	121.89 (10)	C8—C7—H7B	109.6
C6—C1—C7	122.43 (10)	H7A—C7—H7B	108.1
C3—C2—C1	122.99 (11)	O1—C8—N1	122.19 (11)
C3—C2—Cl1	117.80 (9)	O1—C8—C7	121.94 (10)
C1—C2—Cl1	119.20 (9)	N1—C8—C7	115.86 (10)
C4—C3—C2	118.98 (11)	N2—C9—N1	121.19 (10)
C4—C3—H3A	120.5	N2—C9—S1	115.54 (9)
C2—C3—H3A	120.5	N1—C9—S1	123.27 (8)
C5—C4—C3	120.31 (12)	C11—C10—N2	115.85 (11)
C5—C4—H4A	119.8	C11—C10—H10A	122.1
C3—C4—H4A	119.8	N2—C10—H10A	122.1
C4—C5—C6	119.38 (11)	C10—C11—S1	110.26 (9)
C4—C5—H5A	120.3	C10—C11—H11B	124.9
C6—C5—H5A	120.3	S1—C11—H11B	124.9
C5—C6—C1	122.69 (11)

C6—C1—C2—C3	−0.48 (18)	C6—C1—C7—C8	−91.89 (13)
C7—C1—C2—C3	−178.78 (11)	C9—N1—C8—O1	0.06 (19)
C6—C1—C2—Cl1	178.78 (9)	C9—N1—C8—C7	179.00 (10)
C7—C1—C2—Cl1	0.48 (16)	C1—C7—C8—O1	53.64 (15)
C1—C2—C3—C4	0.69 (19)	C1—C7—C8—N1	−125.30 (11)
Cl1—C2—C3—C4	−178.58 (10)	C10—N2—C9—N1	179.79 (11)
C2—C3—C4—C5	−0.38 (19)	C10—N2—C9—S1	−0.23 (13)
C3—C4—C5—C6	−0.09 (19)	C8—N1—C9—N2	174.79 (11)
C4—C5—C6—C1	0.30 (19)	C8—N1—C9—S1	−5.18 (17)
C4—C5—C6—Cl2	−178.67 (10)	C11—S1—C9—N2	0.53 (10)
C2—C1—C6—C5	−0.02 (17)	C11—S1—C9—N1	−179.49 (10)
C7—C1—C6—C5	178.27 (11)	C9—N2—C10—C11	−0.31 (16)
C2—C1—C6—Cl2	178.92 (9)	N2—C10—C11—S1	0.70 (15)
C7—C1—C6—Cl2	−2.79 (16)	C9—S1—C11—C10	−0.66 (10)
C2—C1—C7—C8	86.29 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.890 (19)	2.030 (19)	2.9165 (14)	173.9 (17)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₈Cl₂N₂OS
M_r	287.15
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	7.1278 (4), 8.4434 (4), 10.3637 (6)
α, β, γ (°)	95.341 (4), 106.140 (5), 96.745 (4)
V (Å³)	589.80 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Agilent, 2012)
T_min, T_max	0.909, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10674, 5881, 4481
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.859

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.096, 1.05
No. of reflections	5881
No. of parameters	159
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.30

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

S1—C11	1.7212 (13)	Cl1—C2	1.7436 (12)
S1—C9	1.7306 (11)	Cl2—C6	1.7382 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.890 (19)	2.030 (19)	2.9165 (14)	173.9 (17)

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST–PURSE financial assistance. RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

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