1-(2-Chloro-5-nitro­phen­yl)-3-(2,2-di­methyl­propion­yl)thio­urea

Saeed, A.; Khera, R.A.; Simpson, J.; Stanley, R.G.

doi:10.1107/S1600536809024672

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o1735-o1736

doi:10.1107/S1600536809024672

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1-(2-Chloro-5-nitrophenyl)-3-(2,2-dimethylpropionyl)thiourea

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Jim Simpson ^b and Roderick G. Stanley ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 16 June 2009; accepted 26 June 2009; online 1 July 2009)

With the exception of the C atoms of two of the methyl groups of the tert-butyl substituent, all of the non-H atoms of the title compound, C₁₂H₁₄ClN₃O₃S, lie on a mirror plane. The 2-chloro-5-nitrophenyl and 2,2-dimethylpropionyl substituents are, respectively, cis and trans relative to the thiocarbonyl S atom across the two C—N bonds. Intramolecular N—H⋯O and C—H⋯S hydrogen bonds form S(6) ring motifs, also in the mirror plane. Despite the presence of two N—H subsituents, no intermolecular hydrogen bonds are observed in the crystal structure. Weak π–π contacts [centroid–centroid distances of 4.2903 (17) Å] involving adjacent aromatic rings link the molecules in a head-to-tail fashion above and below the molecular plane.

Related literature

For the use of thiourea derivatives in organic synthesis, see: Eynde & Watte (2003 ); Fu et al. (1999 ); Rashdan et al. (2006 ); Maryanoff et al. (1986 ); Wang et al. (2005 ); Saeed et al. (2008 ); and in analysis, see: Koch (2001 ). For their bioactivity and pharmaceutical applications, see: Upadhyaya & Srivastava (1982 ); Krishnamurthy et al. (1999 ); Blum & Hayes (1979 ); DeBeer et al. (1936 ). For related structures, see: Saeed & Flörke (2007a ,b ); Yusof et al. (2006 , 2008 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₄ClN₃O₃S
M_r = 315.77
Orthorhombic, P n m a
a = 9.529 (2) Å
b = 6.546 (2) Å
c = 22.166 (6) Å
V = 1382.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 89 K
0.36 × 0.09 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.833, T_max = 0.974
12525 measured reflections
1434 independent reflections
1166 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.092
S = 1.09
1434 reflections
130 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯S1	0.95	2.51	3.197 (3)	130
N2—H2N⋯O1	0.97 (3)	1.82 (3)	2.653 (3)	141 (3)

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 and SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999 ); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024672/lh2851sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024672/lh2851Isup2.hkl

checkCIF report

Comment top

Substituted thioureas are versatile building blocks for the synthesis of a variety of heterocyclic compounds with a broad range of useful applications and exhibiting a wide range of bioactivity. Solid-phase Biginelli pyrimidine synthesis (Eynde & Watte, 2003) and synthesis of imidazoline derivatives (Fu et al., 1999) have been carried out using resin-bound thioureas. Pyridyl thioureas are switchable anion receptors (Rashdan et al., 2006); thioureas are also efficient guanylating agents (Maryanoff et al., 1986) while N,N-dialkyl-N-aroyl thioureas are efficient ligands for the separation of platinum group metals (Koch, 2001). Acyl thioureas are well known for their superior pesticidal, fungicidal, antiviral and plant-growth regulatory activities (Upadhyaya & Srivastava, 1982). 1,3-Dialkyl or diaryl thioureas show powerful antifungal activity against plant pathogens Pyricularia oryzae and Drechslera oryzae (Krishnamurthy et al., 1999). Substituted thioureas are potent enhancers of 30S dynein ATPase activity and inhibitors of 14S dynein ATPase activity (Blum & Hayes, 1979). Aryl and alkyl-aryl thioureas display strong hypnotic potency in mice (DeBeer et al., 1936). 1-Aroyl-3-arylthioureas are an exceptionally important group of thioureas which have attracted recent interest. They have been used in the synthesis of imidazole-2-thiones (Wang et al., 2005) and 2-(aroylimino)-3-aryl-4-phenyl-1,3-thiazolines (Saeed et al., 2008). We report here the structure of the title thiourea derivative (I), Fig. 1.

With the exception of the C12 atoms of two methyl groups of the t-butyl substituent all of the non-hydrogen atoms of the title compound, C₁₃H₁₅N₂O₃SCl lie on a mirror plane. Intramolecular N2—H2N···O1 and C9—H9···S1 hydrogen bonds each form a 6-membered ring, also in the mirror plane. Bond distances within the molecule are normal (Allen et al. 1987) and similar to those observed in comparable structures (Saeed & Flörke 2007a,b; Yusof et al. 2006, 2008). Despite the presence of both amide and thioamide groups in the molecule, no intermolecular hydrogen bonds are observed in the crystal structure. Weak π–π contacts between neighbouring C4···C9 rings, Fig 2, with centroid···centroid distances 4.2903 (17)Å and perpendicular distances between the molecular planes of 3.273Å link adjacent molecules above and below the molecular plane along b. These stacks of molecules form sheets parallel to the c axis, Fig. 3.

Related literature top

For the use of thiourea derivatives in organic synthesis, see: Eynde & Watte (2003); Fu et al. (1999); Rashdan et al. (2006); Maryanoff et al. (1986); Wang et al. (2005); Saeed et al. (2008); and in analysis, see: Koch (2001). For their bioactivity and pharmaceutical applications, see: Upadhyaya & Srivastava (1982); Krishnamurthy et al. (1999); Blum & Hayes (1979); DeBeer et al. (1936). For related structures, see: Saeed & Flörke (2007a,b); Yusof et al. (2006, 2008). For reference structural data, see: Allen et al. (1987).

Experimental top

A solution of pivaloyl chloride (10 mmol) in anhydrous acetone (50 ml) was added dropwise to a suspension of potassium thiocyanate (10 mmol) in acetone (30 ml) and the reaction mixture was refluxed for 30 min. After cooling to room temperature, a solution of 2-chloro-5-nitroaniline (1.28 g, 10 mmol) in acetone (10 ml) was added and the resulting mixture refluxed for 2 h. The reaction mixture was poured into cold water and the thiourea was precipitated as a white solid. Recrystallization from ethanol gave colorless crystals of (I) (8.6 mmol, 86%). IR (KBr) cm^-1: 3351 (free NH), 3200 (assoc. NH), 1667 (CO), 1610 (arom.), 1529 (thioureido I) 1325 II, 1160 III, 744, 762.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 and SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).

Figures top

	Fig. 1. The structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level. Intramolecular hydrogen bonds are drawn as dashed lines. The atom labeled C12A is related to the C12 atom by the symmetry operation x, -y + 1/2, z.
	Fig. 2. π–π interactions for (1).
	Fig. 3. Crystal packing for (I) viewed down the a axis.

1-(2-Chloro-5-nitrophenyl)-3-(2,2-dimethylpropanoyl)thiourea top

Crystal data top

C₁₂H₁₄ClN₃O₃S	F(000) = 656
M_r = 315.77	D_x = 1.517 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2410 reflections
a = 9.529 (2) Å	θ = 2.3–24.6°
b = 6.546 (2) Å	µ = 0.44 mm⁻¹
c = 22.166 (6) Å	T = 89 K
V = 1382.7 (7) Å³	Needle, colourless
Z = 4	0.36 × 0.09 × 0.06 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1434 independent reflections
Radiation source: fine-focus sealed tube	1166 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ω scans	θ_max = 25.7°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −11→11
T_min = 0.833, T_max = 0.974	k = −6→8
12525 measured reflections	l = −26→26

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0461P)² + 0.3426P] where P = (F_o² + 2F_c²)/3
1434 reflections	(Δ/σ)_max < 0.001
130 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₂H₁₄ClN₃O₃S	V = 1382.7 (7) Å³
M_r = 315.77	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 9.529 (2) Å	µ = 0.44 mm⁻¹
b = 6.546 (2) Å	T = 89 K
c = 22.166 (6) Å	0.36 × 0.09 × 0.06 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1434 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	1166 reflections with I > 2σ(I)
T_min = 0.833, T_max = 0.974	R_int = 0.069
12525 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.27 e Å⁻³
1434 reflections	Δρ_min = −0.43 e Å⁻³
130 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
C1	0.1946 (3)	0.2500	0.36075 (12)	0.0163 (6)
O1	0.3187 (2)	0.2500	0.34713 (8)	0.0217 (5)
N1	0.1523 (3)	0.2500	0.42088 (10)	0.0184 (5)
H1N	0.070 (4)	0.2500	0.4268 (16)	0.037 (11)*
C2	0.2314 (3)	0.2500	0.47417 (11)	0.0143 (6)
S1	0.14289 (7)	0.2500	0.53901 (3)	0.0192 (2)
N2	0.3713 (2)	0.2500	0.46466 (10)	0.0143 (5)
H2N	0.397 (3)	0.2500	0.4222 (15)	0.030 (9)*
C4	0.4846 (3)	0.2500	0.50580 (12)	0.0130 (6)
C5	0.6210 (3)	0.2500	0.48174 (11)	0.0147 (6)
Cl1	0.64439 (7)	0.2500	0.40389 (3)	0.0181 (2)
C6	0.7399 (3)	0.2500	0.51801 (12)	0.0168 (6)
H6	0.8305	0.2500	0.5002	0.020*
C7	0.7261 (3)	0.2500	0.58025 (12)	0.0183 (6)
H7	0.8060	0.2500	0.6059	0.022*
C8	0.5911 (3)	0.2500	0.60368 (11)	0.0167 (6)
N3	0.5743 (3)	0.2500	0.67027 (10)	0.0204 (5)
O2	0.6808 (2)	0.2500	0.70124 (9)	0.0286 (5)
O3	0.4544 (2)	0.2500	0.69074 (9)	0.0317 (6)
C9	0.4711 (3)	0.2500	0.56877 (11)	0.0147 (6)
H9	0.3810	0.2500	0.5871	0.018*
C10	0.0727 (3)	0.2500	0.31561 (11)	0.0170 (6)
C11	0.1330 (3)	0.2500	0.25185 (13)	0.0308 (8)
H11A	0.059 (4)	0.2500	0.2261 (16)	0.037*
H11B	0.188 (2)	0.132 (3)	0.2442 (10)	0.037*
C12	−0.0158 (2)	0.0571 (3)	0.32488 (9)	0.0229 (5)
H12A	−0.0897	0.0515	0.2942	0.034*
H12B	−0.0585	0.0602	0.3651	0.034*
H12C	0.0442	−0.0638	0.3213	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0149 (14)	0.0200 (15)	0.0142 (14)	0.000	−0.0001 (11)	0.000
O1	0.0135 (10)	0.0360 (12)	0.0155 (9)	0.000	0.0018 (8)	0.000
N1	0.0109 (13)	0.0317 (14)	0.0125 (11)	0.000	0.0003 (10)	0.000
C2	0.0129 (13)	0.0185 (14)	0.0113 (13)	0.000	−0.0021 (10)	0.000
S1	0.0149 (4)	0.0307 (4)	0.0121 (3)	0.000	0.0020 (3)	0.000
N2	0.0124 (12)	0.0196 (12)	0.0110 (11)	0.000	−0.0008 (9)	0.000
C4	0.0134 (13)	0.0108 (13)	0.0146 (13)	0.000	−0.0025 (10)	0.000
C5	0.0183 (14)	0.0129 (13)	0.0128 (13)	0.000	−0.0007 (11)	0.000
Cl1	0.0149 (4)	0.0262 (4)	0.0132 (3)	0.000	0.0020 (2)	0.000
C6	0.0128 (14)	0.0169 (14)	0.0209 (14)	0.000	0.0010 (11)	0.000
C7	0.0190 (15)	0.0148 (14)	0.0210 (14)	0.000	−0.0057 (12)	0.000
C8	0.0213 (15)	0.0150 (14)	0.0139 (13)	0.000	−0.0018 (11)	0.000
N3	0.0258 (14)	0.0213 (13)	0.0142 (12)	0.000	−0.0011 (10)	0.000
O2	0.0284 (12)	0.0391 (13)	0.0182 (10)	0.000	−0.0114 (9)	0.000
O3	0.0266 (12)	0.0527 (15)	0.0157 (10)	0.000	0.0031 (9)	0.000
C9	0.0165 (14)	0.0122 (13)	0.0154 (13)	0.000	−0.0002 (11)	0.000
C10	0.0147 (14)	0.0258 (15)	0.0104 (13)	0.000	−0.0018 (11)	0.000
C11	0.0193 (17)	0.062 (2)	0.0115 (14)	0.000	−0.0013 (13)	0.000
C12	0.0222 (11)	0.0220 (11)	0.0245 (10)	0.0000 (9)	−0.0078 (8)	−0.0021 (9)

Geometric parameters (Å, º) top

C1—O1	1.221 (3)	C7—C8	1.387 (4)
C1—N1	1.392 (3)	C7—H7	0.9500
C1—C10	1.533 (4)	C8—C9	1.380 (4)
N1—C2	1.401 (3)	C8—N3	1.485 (3)
N1—H1N	0.80 (4)	N3—O2	1.226 (3)
C2—N2	1.349 (3)	N3—O3	1.229 (3)
C2—S1	1.667 (3)	C9—H9	0.9500
N2—C4	1.414 (3)	C10—C11	1.526 (4)
N2—H2N	0.97 (3)	C10—C12	1.533 (3)
C4—C9	1.402 (3)	C10—C12ⁱ	1.533 (3)
C4—C5	1.405 (4)	C11—H11A	0.91 (4)
C5—C6	1.389 (4)	C11—H11B	0.95 (2)
C5—Cl1	1.740 (3)	C12—H12A	0.9800
C6—C7	1.386 (4)	C12—H12B	0.9800
C6—H6	0.9500	C12—H12C	0.9800

O1—C1—N1	121.1 (2)	C9—C8—C7	123.9 (2)
O1—C1—C10	124.9 (2)	C9—C8—N3	117.9 (2)
N1—C1—C10	113.9 (2)	C7—C8—N3	118.2 (2)
C1—N1—C2	130.6 (2)	O2—N3—O3	124.3 (2)
C1—N1—H1N	116 (3)	O2—N3—C8	117.9 (2)
C2—N1—H1N	113 (3)	O3—N3—C8	117.8 (2)
N2—C2—N1	113.6 (2)	C8—C9—C4	118.8 (2)
N2—C2—S1	129.4 (2)	C8—C9—H9	120.6
N1—C2—S1	117.0 (2)	C4—C9—H9	120.6
C2—N2—C4	130.8 (2)	C11—C10—C12	109.35 (14)
C2—N2—H2N	113.7 (19)	C11—C10—C12ⁱ	109.35 (14)
C4—N2—H2N	115.5 (19)	C12—C10—C12ⁱ	111.0 (2)
C9—C4—C5	117.6 (2)	C11—C10—C1	108.6 (2)
C9—C4—N2	124.9 (2)	C12—C10—C1	109.25 (14)
C5—C4—N2	117.5 (2)	C12ⁱ—C10—C1	109.25 (14)
C6—C5—C4	122.3 (2)	C10—C11—H11A	107 (2)
C6—C5—Cl1	118.0 (2)	C10—C11—H11B	111.9 (14)
C4—C5—Cl1	119.7 (2)	H11A—C11—H11B	108.5 (18)
C7—C6—C5	119.9 (2)	C10—C12—H12A	109.5
C7—C6—H6	120.0	C10—C12—H12B	109.5
C5—C6—H6	120.0	H12A—C12—H12B	109.5
C6—C7—C8	117.4 (2)	C10—C12—H12C	109.5
C6—C7—H7	121.3	H12A—C12—H12C	109.5
C8—C7—H7	121.3	H12B—C12—H12C	109.5

O1—C1—N1—C2	0.0	C6—C7—C8—N3	180.0
C10—C1—N1—C2	180.0	C9—C8—N3—O2	180.0
C1—N1—C2—N2	0.0	C7—C8—N3—O2	0.000 (1)
C1—N1—C2—S1	180.0	C9—C8—N3—O3	0.000 (1)
N1—C2—N2—C4	180.0	C7—C8—N3—O3	180.0
S1—C2—N2—C4	0.000 (1)	C7—C8—C9—C4	0.000 (1)
C2—N2—C4—C9	0.000 (1)	N3—C8—C9—C4	180.0
C2—N2—C4—C5	180.0	C5—C4—C9—C8	0.000 (1)
C9—C4—C5—C6	0.0	N2—C4—C9—C8	180.0
N2—C4—C5—C6	180.0	O1—C1—C10—C11	0.0
C9—C4—C5—Cl1	180.0	N1—C1—C10—C11	180.0
N2—C4—C5—Cl1	0.0	O1—C1—C10—C12	119.21 (15)
C4—C5—C6—C7	0.000 (1)	N1—C1—C10—C12	−60.79 (15)
Cl1—C5—C6—C7	180.0	O1—C1—C10—C12ⁱ	−119.21 (15)
C5—C6—C7—C8	0.000 (1)	N1—C1—C10—C12ⁱ	60.79 (15)
C6—C7—C8—C9	0.000 (1)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···S1	0.95	2.51	3.197 (3)	130
N2—H2N···O1	0.97 (3)	1.82 (3)	2.653 (3)	141 (3)

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄ClN₃O₃S
M_r	315.77
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	89
a, b, c (Å)	9.529 (2), 6.546 (2), 22.166 (6)
V (Å³)	1382.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.36 × 0.09 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.833, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	12525, 1434, 1166
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.092, 1.09
No. of reflections	1434
No. of parameters	130
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.43

Computer programs: APEX2 (Bruker, 2006), APEX2 and SAINT (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···S1	0.95	2.51	3.197 (3)	129.5
N2—H2N···O1	0.97 (3)	1.82 (3)	2.653 (3)	141 (3)

Acknowledgements

We thank the University of Otago for the purchase of the diffractometer.

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