1-(6-Methyl-4-phenyl-2-sulfanyl­idene-1,2,3,4-tetrahydro­pyrimidin-5-yl)ethanone

Anuradha, N.; Thiruvalluvar, A.; Chitra, S.; Pandiarajan, K.; Butcher, R.J.

doi:10.1107/S1600536810031296

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2280

https://doi.org/10.1107/S1600536810031296

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1-(6-Methyl-4-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone

N. Anuradha,^a A. Thiruvalluvar,^a ^* S. Chitra,^b ‡ K. Pandiarajan ^b and R. J. Butcher ^c

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, ^bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: athiru@vsnl.net

(Received 3 August 2010; accepted 4 August 2010; online 11 August 2010)

In the title compound, C₁₃H₁₄N₂OS, the heterocyclic ring adopts a flattened boat conformation with the plane through the four coplanar atoms making a dihedral angle of 86.90 (13)° with the phenyl ring, which adopts an axial orientation. The thionyl, acetyl and methyl groups all have equatorial orientations. Intermolecular N—H⋯O, N—H⋯S and C—H⋯O hydrogen bonds are found in the crystal structure.

Related literature

For chemical and biological applications of dihydropyrimidinone derivatives, see: Chitra et al. (2010 ). For their applications and for related structures, see: Anuradha et al. (2008 , 2009a ,b ,c ).

Experimental

Crystal data

C₁₃H₁₄N₂OS
M_r = 246.33
Monoclinic, P 2₁ /c
a = 7.8849 (10) Å
b = 7.2054 (5) Å
c = 21.555 (3) Å
β = 94.401 (12)°
V = 1221.0 (2) Å³
Z = 4
Cu Kα radiation
μ = 2.23 mm⁻¹
T = 295 K
0.44 × 0.31 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.307, T_max = 1.000
4776 measured reflections
2531 independent reflections
2226 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.236
S = 1.22
2531 reflections
164 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 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—H1⋯O15ⁱ	0.80 (6)	2.14 (6)	2.898 (5)	158 (5)
N3—H3⋯S2ⁱⁱ	0.88 (4)	2.57 (4)	3.436 (4)	168 (4)
C61—H61B⋯O15ⁱ	0.96	2.54	3.333 (6)	140
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810031296/hg2697sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031296/hg2697Isup2.hkl

checkCIF report

Comment top

Dihydropyrimidinone derivatives exhibit a wide range of biological effects such as antibacterial and antifungal activities (Chitra et al., 2010). The crystal structures of four very closely related compounds have recently been reported [Anuradha et al., (2008, 2009a,b,c)]. This study of the title compound, was undertaken to compare the biological activity and structure of dihydropyrimidin-2(1H)-thione and its corresponding 2(1H)-one (Anuradha et al., 2008).

In the title molecule, C₁₃H₁₄N₂OS, Fig.1., the heterocyclic ring adopts a flattened boat conformation with the plane through the four coplanar atoms (C2,N3,C5,C6) making a dihedral angle of 86.90 (13)° with the phenyl ring, which adopts an axial orientation. The thionyl, acetyl and methyl groups all have equatorial orientations. Intermolecular N1—H1···O15, N3—H3···S2 and C61—H61B···O15 hydrogen bonds are found in the crystal structure (Fig. 2, Table 1).

Related literature top

For chemical and biological applications of dihydropyrimidinone derivatives, see: Chitra et al. (2010). For their applications and for related structures, see: Anuradha et al. (2008, 2009a,b,c).

Experimental top

A solution of acetylacetone (1.0012 g, 0.01 mol), benzaldehyde (1.06 g, 0.01 mol) and thiourea (1.149 g, 0.015 mol) was heated under reflux in the presence of calcium fluoride (0.0780 g, 0.001 mol) for 2 h (monitored by TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and poured into crushed ice. The crude product containing also the catalyst was collected on a Buchner funnel by filtration. The mixture of the product and the catalyst was digested in methanol (40 ml). The undissolved catalyst was removed by filtration. The crude product was obtained by evaporation of methanol and further purified by recrystallization from hot ethanol to afford the pure title compound. Yield 96% (2.8 g).

Structure description top

For chemical and biological applications of dihydropyrimidinone derivatives, see: Chitra et al. (2010). For their applications and for related structures, see: Anuradha et al. (2008, 2009a,b,c).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

1-(6-Methyl-4-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone top

Crystal data top

C₁₃H₁₄N₂OS	F(000) = 520
M_r = 246.33	D_x = 1.340 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 523.5 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 7.8849 (10) Å	Cell parameters from 3041 reflections
b = 7.2054 (5) Å	θ = 5.6–77.1°
c = 21.555 (3) Å	µ = 2.23 mm⁻¹
β = 94.401 (12)°	T = 295 K
V = 1221.0 (2) Å³	Prism, colourless
Z = 4	0.44 × 0.31 × 0.16 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2531 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2226 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.5081 pixels mm^-1	θ_max = 77.3°, θ_min = 5.6°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −5→9
T_min = 0.307, T_max = 1.000	l = −24→27
4776 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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ²(F_o²) + (0.0912P)² + 1.9142P] where P = (F_o² + 2F_c²)/3
2531 reflections	(Δ/σ)_max = 0.001
164 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₃H₁₄N₂OS	V = 1221.0 (2) Å³
M_r = 246.33	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 7.8849 (10) Å	µ = 2.23 mm⁻¹
b = 7.2054 (5) Å	T = 295 K
c = 21.555 (3) Å	0.44 × 0.31 × 0.16 mm
β = 94.401 (12)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2531 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2226 reflections with I > 2σ(I)
T_min = 0.307, T_max = 1.000	R_int = 0.029
4776 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	Δρ_max = 0.62 e Å⁻³
2531 reflections	Δρ_min = −0.30 e Å⁻³
164 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
S2	0.49206 (14)	−0.24803 (15)	0.06167 (5)	0.0540 (4)
O15	0.7124 (6)	0.5124 (5)	0.21330 (16)	0.0771 (13)
N1	0.6473 (5)	−0.1160 (5)	0.16583 (16)	0.0512 (11)
N3	0.5890 (4)	0.0977 (5)	0.08897 (16)	0.0456 (10)
C2	0.5819 (5)	−0.0771 (5)	0.10664 (18)	0.0444 (11)
C4	0.6849 (5)	0.2449 (5)	0.12284 (18)	0.0441 (11)
C5	0.7078 (5)	0.1972 (5)	0.19220 (17)	0.0432 (11)
C6	0.6954 (5)	0.0179 (6)	0.21040 (18)	0.0461 (11)
C15	0.7438 (6)	0.3575 (6)	0.23320 (19)	0.0516 (14)
C16	0.8242 (9)	0.3391 (8)	0.2982 (2)	0.080 (2)
C41	0.8574 (5)	0.2795 (5)	0.09762 (17)	0.0444 (11)
C42	0.9599 (6)	0.1317 (7)	0.0816 (2)	0.0585 (16)
C43	1.1194 (6)	0.1664 (8)	0.0619 (2)	0.0673 (17)
C44	1.1803 (6)	0.3452 (9)	0.0582 (2)	0.0661 (16)
C45	1.0782 (6)	0.4909 (8)	0.0726 (2)	0.0617 (16)
C46	0.9178 (6)	0.4592 (7)	0.0921 (2)	0.0548 (12)
C61	0.7244 (7)	−0.0627 (6)	0.27457 (19)	0.0603 (14)
H1	0.642 (7)	−0.225 (8)	0.173 (2)	0.061 (15)*
H3	0.565 (5)	0.118 (6)	0.049 (2)	0.047 (11)*
H4	0.61861	0.35972	0.11825	0.0528*
H16A	0.86487	0.45818	0.31279	0.1193*
H16B	0.91778	0.25375	0.29855	0.1193*
H16C	0.74161	0.29367	0.32496	0.1193*
H42	0.92086	0.01038	0.08427	0.0701*
H43	1.18682	0.06759	0.05095	0.0807*
H44	1.28923	0.36677	0.04607	0.0796*
H45	1.11727	0.61201	0.06913	0.0739*
H46	0.84985	0.55915	0.10164	0.0657*
H61A	0.84360	−0.05933	0.28748	0.0904*
H61B	0.68524	−0.18890	0.27422	0.0904*
H61C	0.66278	0.00853	0.30303	0.0904*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S2	0.0612 (7)	0.0456 (6)	0.0530 (6)	−0.0106 (5)	−0.0089 (4)	−0.0029 (4)
O15	0.128 (3)	0.0362 (17)	0.065 (2)	0.0011 (19)	−0.007 (2)	−0.0031 (14)
N1	0.070 (2)	0.0316 (17)	0.0496 (18)	−0.0030 (16)	−0.0112 (15)	0.0024 (14)
N3	0.0482 (17)	0.0417 (18)	0.0448 (17)	−0.0042 (14)	−0.0101 (13)	0.0047 (14)
C2	0.0420 (18)	0.041 (2)	0.049 (2)	−0.0012 (15)	−0.0037 (15)	−0.0004 (16)
C4	0.049 (2)	0.0365 (19)	0.0455 (19)	−0.0013 (15)	−0.0050 (15)	0.0027 (15)
C5	0.0472 (19)	0.0370 (19)	0.0447 (19)	0.0005 (15)	−0.0002 (15)	0.0012 (15)
C6	0.053 (2)	0.041 (2)	0.0433 (19)	−0.0006 (17)	−0.0027 (15)	0.0009 (16)
C15	0.069 (3)	0.036 (2)	0.050 (2)	−0.0061 (18)	0.0050 (18)	−0.0008 (16)
C16	0.123 (5)	0.055 (3)	0.058 (3)	−0.021 (3)	−0.015 (3)	−0.006 (2)
C41	0.0477 (19)	0.045 (2)	0.0390 (17)	0.0012 (16)	−0.0063 (14)	0.0027 (15)
C42	0.062 (3)	0.050 (2)	0.063 (3)	0.004 (2)	0.001 (2)	0.005 (2)
C43	0.055 (3)	0.075 (3)	0.072 (3)	0.013 (2)	0.005 (2)	−0.001 (3)
C44	0.048 (2)	0.093 (4)	0.057 (2)	−0.008 (2)	0.0027 (19)	0.005 (3)
C45	0.061 (3)	0.068 (3)	0.055 (2)	−0.014 (2)	−0.002 (2)	0.003 (2)
C46	0.060 (2)	0.052 (2)	0.052 (2)	−0.006 (2)	0.0009 (18)	0.0023 (18)
C61	0.087 (3)	0.044 (2)	0.048 (2)	−0.005 (2)	−0.007 (2)	0.0057 (18)

Geometric parameters (Å, º) top

S2—C2	1.689 (4)	C42—C43	1.381 (7)
O15—C15	1.214 (6)	C43—C44	1.379 (8)
N1—C2	1.368 (5)	C44—C45	1.373 (8)
N1—C6	1.394 (5)	C45—C46	1.382 (7)
N3—C2	1.318 (5)	C4—H4	0.9800
N3—C4	1.465 (5)	C16—H16A	0.9600
N1—H1	0.80 (6)	C16—H16B	0.9600
N3—H3	0.88 (4)	C16—H16C	0.9600
C4—C41	1.524 (6)	C42—H42	0.9300
C4—C5	1.531 (5)	C43—H43	0.9300
C5—C6	1.356 (6)	C44—H44	0.9300
C5—C15	1.469 (6)	C45—H45	0.9300
C6—C61	1.501 (6)	C46—H46	0.9300
C15—C16	1.499 (6)	C61—H61A	0.9600
C41—C46	1.388 (6)	C61—H61B	0.9600
C41—C42	1.396 (6)	C61—H61C	0.9600

S2···N3ⁱ	3.436 (4)	C16···H61C	2.7100
S2···H45ⁱⁱ	3.1400	C16···H61A	2.8900
S2···H16Cⁱⁱⁱ	3.1900	C42···H16A^ix	2.8600
S2···H3ⁱ	2.57 (4)	C43···H16A^ix	3.0800
S2···H44^iv	3.1200	C45···H61A^viii	3.0500
O15···N1^v	2.898 (5)	C46···H61A^viii	3.0900
O15···C41	3.283 (5)	C61···H16B	2.7700
O15···C46	3.201 (6)	C61···H16C	2.7900
O15···C61^v	3.333 (6)	H1···O15^vi	2.14 (6)
O15···H1^v	2.14 (6)	H1···H61B	2.2000
O15···H4	2.3900	H3···S2ⁱ	2.57 (4)
O15···H46	2.7400	H4···O15	2.3900
O15···H61B^v	2.5400	H4···H46	2.3700
N1···O15^vi	2.898 (5)	H16A···C42^viii	2.8600
N3···S2ⁱ	3.436 (4)	H16A···C43^viii	3.0800
N3···H42	2.7000	H16B···C6	3.0100
C2···C42	3.418 (6)	H16B···C61	2.7700
C15···C46	3.509 (6)	H16B···H61A	2.3400
C16···C61	3.033 (7)	H16C···C61	2.7900
C41···O15	3.283 (5)	H16C···H61C	2.1900
C42···C2	3.418 (6)	H16C···S2^x	3.1900
C44···C46^vii	3.563 (6)	H42···N3	2.7000
C44···C45^vii	3.552 (7)	H42···C2	2.8200
C45···C46^vii	3.571 (6)	H44···S2^iv	3.1200
C45···C61^viii	3.555 (6)	H45···S2^xi	3.1400
C45···C44^vii	3.552 (7)	H46···O15	2.7400
C45···C45^vii	3.277 (6)	H46···H4	2.3700
C46···C15	3.509 (6)	H61A···C16	2.8900
C46···O15	3.201 (6)	H61A···H16B	2.3400
C46···C45^vii	3.571 (6)	H61A···C45^ix	3.0500
C46···C44^vii	3.563 (6)	H61A···C46^ix	3.0900
C61···C45^ix	3.555 (6)	H61B···O15^vi	2.5400
C61···C16	3.033 (7)	H61B···H1	2.2000
C61···O15^vi	3.333 (6)	H61C···C15	3.0200
C2···H42	2.8200	H61C···C16	2.7100
C6···H16B	3.0100	H61C···H16C	2.1900
C15···H61C	3.0200

C2—N1—C6	124.4 (3)	C44—C45—C46	120.6 (5)
C2—N3—C4	125.4 (3)	C41—C46—C45	120.6 (5)
C2—N1—H1	111 (3)	N3—C4—H4	108.00
C6—N1—H1	124 (3)	C5—C4—H4	108.00
C2—N3—H3	116 (3)	C41—C4—H4	108.00
C4—N3—H3	116 (3)	C15—C16—H16A	109.00
S2—C2—N1	119.8 (3)	C15—C16—H16B	109.00
S2—C2—N3	123.8 (3)	C15—C16—H16C	110.00
N1—C2—N3	116.4 (3)	H16A—C16—H16B	109.00
N3—C4—C5	110.0 (3)	H16A—C16—H16C	109.00
C5—C4—C41	110.1 (3)	H16B—C16—H16C	109.00
N3—C4—C41	112.4 (3)	C41—C42—H42	120.00
C4—C5—C6	119.4 (3)	C43—C42—H42	120.00
C4—C5—C15	114.5 (3)	C42—C43—H43	119.00
C6—C5—C15	126.2 (4)	C44—C43—H43	119.00
C5—C6—C61	128.7 (4)	C43—C44—H44	120.00
N1—C6—C5	118.8 (4)	C45—C44—H44	120.00
N1—C6—C61	112.4 (4)	C44—C45—H45	120.00
O15—C15—C16	118.1 (4)	C46—C45—H45	120.00
C5—C15—C16	122.8 (4)	C41—C46—H46	120.00
O15—C15—C5	119.0 (4)	C45—C46—H46	120.00
C4—C41—C42	120.9 (3)	C6—C61—H61A	110.00
C4—C41—C46	120.3 (3)	C6—C61—H61B	109.00
C42—C41—C46	118.8 (4)	C6—C61—H61C	109.00
C41—C42—C43	119.7 (5)	H61A—C61—H61B	109.00
C42—C43—C44	121.1 (5)	H61A—C61—H61C	109.00
C43—C44—C45	119.2 (5)	H61B—C61—H61C	109.00

C6—N1—C2—S2	−167.7 (3)	C4—C5—C6—N1	−5.6 (6)
C6—N1—C2—N3	10.2 (6)	C4—C5—C6—C61	175.5 (4)
C2—N1—C6—C5	−12.3 (6)	C15—C5—C6—N1	175.0 (4)
C2—N1—C6—C61	166.8 (4)	C15—C5—C6—C61	−3.9 (7)
C4—N3—C2—S2	−171.4 (3)	C4—C5—C15—O15	17.8 (6)
C4—N3—C2—N1	10.9 (6)	C4—C5—C15—C16	−159.8 (5)
C2—N3—C4—C5	−25.7 (5)	C6—C5—C15—O15	−162.8 (5)
C2—N3—C4—C41	97.4 (4)	C6—C5—C15—C16	19.6 (7)
N3—C4—C5—C6	22.0 (5)	C4—C41—C42—C43	−176.7 (4)
N3—C4—C5—C15	−158.6 (3)	C46—C41—C42—C43	1.3 (6)
C41—C4—C5—C6	−102.5 (4)	C4—C41—C46—C45	176.3 (4)
C41—C4—C5—C15	77.0 (4)	C42—C41—C46—C45	−1.6 (6)
N3—C4—C41—C42	−42.5 (5)	C41—C42—C43—C44	0.5 (7)
N3—C4—C41—C46	139.6 (4)	C42—C43—C44—C45	−2.0 (7)
C5—C4—C41—C42	80.5 (4)	C43—C44—C45—C46	1.6 (7)
C5—C4—C41—C46	−97.4 (4)	C44—C45—C46—C41	0.2 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O15^vi	0.80 (6)	2.14 (6)	2.898 (5)	158 (5)
N3—H3···S2ⁱ	0.88 (4)	2.57 (4)	3.436 (4)	168 (4)
C61—H61B···O15^vi	0.96	2.54	3.333 (6)	140

Symmetry codes: (i) −x+1, −y, −z; (vi) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂OS
M_r	246.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.8849 (10), 7.2054 (5), 21.555 (3)
β (°)	94.401 (12)
V (Å³)	1221.0 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.23
Crystal size (mm)	0.44 × 0.31 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.307, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4776, 2531, 2226
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.236, 1.22
No. of reflections	2531
No. of parameters	164
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.30

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O15ⁱ	0.80 (6)	2.14 (6)	2.898 (5)	158 (5)
N3—H3···S2ⁱⁱ	0.88 (4)	2.57 (4)	3.436 (4)	168 (4)
C61—H61B···O15ⁱ	0.96	2.54	3.333 (6)	140

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

Footnotes

‡Current address: Department of Chemistry, Sri Jayaram Engineering College, Cuddalore 607 003, Tamilnadu, India.

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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