6-Methyl-2,3,4,9-tetra­hydro-1H-carbazole-1-thione

Archana, R.; Prabakaran, K.; Rajendra Prasad, K.J.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S1600536811019246

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1642

doi:10.1107/S1600536811019246

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6-Methyl-2,3,4,9-tetrahydro-1H-carbazole-1-thione

R. Archana,^a K. Prabakaran,^b K. J. Rajendra Prasad,^b A. Thiruvalluvar ^a ^* and R. J. Butcher ^c

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 17 May 2011; accepted 20 May 2011; online 11 June 2011)

In the title molecule, C₁₃H₁₃NS, the dihedral angle between the benzene ring and the fused pyrrole ring is 0.71 (8)° and the cyclohexene ring is in an envelope form. The (CH₂)₃ atoms of the cyclohexene ring are disordered over two positions; the site-occupancy factor for the major component refined to 0.862 (4). In the crystal, intermolecular N—H⋯S hydrogen bonds lead to the formation of centrosymmetric aggregates via an R₂²(10) ring.

Related literature

For the synthesis of fused carbazole nuclei, see: Pelly et al. (2005 ). For heterocycle-annulated tetra-, penta- and hexacyclic carbazole derivatives, see: Chattopadhyay et al. (2006 ). For the preparation of 1-oxo compounds via their corresponding hydrazones, see: Rajendra Prasad & Vijayalakshmi (1994 ). For related structures, see: Archana et al. (2010 ); Thomas Gunaseelan et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₃NS
M_r = 215.31
Triclinic, $[P \overline 1]$
a = 7.0846 (4) Å
b = 9.5287 (7) Å
c = 9.6384 (6) Å
α = 115.009 (7)°
β = 104.901 (6)°
γ = 98.074 (6)°
V = 546.28 (8) Å³
Z = 2
Cu Kα radiation
μ = 2.31 mm⁻¹
T = 295 K
0.46 × 0.28 × 0.21 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 = 0.609, T_max = 1.000
3471 measured reflections
2102 independent reflections
1924 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.133
S = 1.06
2102 reflections
145 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯S1ⁱ	0.86 (2)	2.77 (3)	3.4955 (15)	143 (2)
Symmetry code: (i) -x+2, -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: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019246/tk2746sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019246/tk2746Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019246/tk2746Isup3.cml

checkCIF report

Comment top

The development of methods for the synthesis of fused carbazole nuclei is becoming increasingly important as a result of the number of natural and synthetic carbazoles that display biological activity (Pelly et al., 2005). Heterocycle-annulated tetra-, penta- and hexa-cyclic carbazole derivatives have been developed using successive applications of three atom economic processes, viz., Claisen rearrangement, olefin metathesis and Diels-Alder reactions (Chattopadhyay et al., 2006). The preparation of 1-oxo compounds via their corresponding hydrazones has been reported (Rajendra Prasad & Vijayalakshmi, 1994). Archana et al. (2010) and Thomas Gunaseelan et al. (2009) have reported the crystal structures of substituted carbazole derivatives, in which the carbazole units are not planar.

In the title molecule, Fig. 1, the dihedral angle between the benzene ring and the fused pyrrole ring is 0.71 (8) °. The cyclohexene ring is in envelope form. Three C atoms (C2A, C3A, C4A) of the cyclohexene ring, with their attached H atoms are disordered over two positions; the site-occupancy factors are ca 0.86 and 0.14. Intermolecular N—H···S hydrogen bonds form a R²₂(10) (Bernstein et al., 1995) ring in the crystal structure (Table 1 & Fig. 2).

Related literature top

For the synthesis of fused carbazole nuclei, see: Pelly et al. (2005). For heterocycle-annulated tetra-, penta- and hexacyclic carbazole derivatives, see: Chattopadhyay et al. (2006). For the preparation of 1-oxo compounds via their corresponding hydrazones, see: Rajendra Prasad & Vijayalakshmi (1994). For related structures, see: Archana et al. (2010); Thomas Gunaseelan et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.199 g, 0.001 mol) and Lawesson's reagent (0.404 g, 0.001 mol) was refluxed in pyridine on an oil bath pre-heated to 383 K for 6 h. The contents were poured onto cold water and neutralized using 1:1 HCl, filtered and dried. The product was recrystallized from ethanol. The yield was 0.154 g (72%).

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); 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. Unit cell contents for (I), viewed down the a axis, showing the formation of a R²₂(10) ring.

6-Methyl-2,3,4,9-tetrahydro-1H-carbazole-1-thione top

Crystal data top

C₁₃H₁₃NS	Z = 2
M_r = 215.31	F(000) = 228
Triclinic, P1	D_x = 1.309 Mg m⁻³
Hall symbol: -P 1	Melting point: 356 K
a = 7.0846 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.5287 (7) Å	Cell parameters from 2595 reflections
c = 9.6384 (6) Å	θ = 5.3–72.6°
α = 115.009 (7)°	µ = 2.31 mm⁻¹
β = 104.901 (6)°	T = 295 K
γ = 98.074 (6)°	Chunk, orange
V = 546.28 (8) Å³	0.46 × 0.28 × 0.21 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2102 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 10.5081 pixels mm^-1	θ_max = 72.8°, θ_min = 5.3°
ω scans	h = −7→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
T_min = 0.609, T_max = 1.000	l = −9→11
3471 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0834P)² + 0.089P] where P = (F_o² + 2F_c²)/3
2102 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.33 e Å⁻³
3 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₃H₁₃NS	γ = 98.074 (6)°
M_r = 215.31	V = 546.28 (8) Å³
Triclinic, P1	Z = 2
a = 7.0846 (4) Å	Cu Kα radiation
b = 9.5287 (7) Å	µ = 2.31 mm⁻¹
c = 9.6384 (6) Å	T = 295 K
α = 115.009 (7)°	0.46 × 0.28 × 0.21 mm
β = 104.901 (6)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2102 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1924 reflections with I > 2σ(I)
T_min = 0.609, T_max = 1.000	R_int = 0.022
3471 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	3 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.33 e Å⁻³
2102 reflections	Δρ_min = −0.22 e Å⁻³
145 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	Occ. (<1)
S1	1.12016 (7)	0.28362 (5)	0.07548 (6)	0.0567 (1)
N9	0.79545 (19)	0.08614 (14)	0.14611 (15)	0.0412 (3)
C1	0.9615 (3)	0.34787 (18)	0.16910 (19)	0.0438 (4)
C2A	0.9571 (3)	0.5227 (2)	0.2371 (3)	0.0611 (6)	0.862 (4)
C3A	0.7579 (4)	0.5495 (2)	0.2548 (3)	0.0590 (7)	0.862 (4)
C4A	0.6807 (3)	0.47256 (19)	0.3468 (2)	0.0531 (5)	0.862 (4)
C4C	0.6904 (3)	0.30147 (17)	0.27848 (18)	0.0421 (4)
C4D	0.5783 (2)	0.16637 (17)	0.27860 (17)	0.0396 (4)
C5	0.4231 (3)	0.14228 (19)	0.33927 (19)	0.0443 (4)
C6	0.3399 (2)	−0.00860 (19)	0.31681 (18)	0.0430 (4)
C7	0.4130 (2)	−0.13824 (18)	0.23121 (19)	0.0444 (4)
C8	0.5640 (2)	−0.12039 (18)	0.16959 (19)	0.0426 (4)
C8A	0.6473 (2)	0.03337 (17)	0.19299 (17)	0.0382 (4)
C9A	0.8222 (2)	0.24863 (17)	0.19625 (18)	0.0406 (4)
C16	0.1720 (3)	−0.0386 (2)	0.3790 (2)	0.0530 (5)
C4B	0.6807 (3)	0.47256 (19)	0.3468 (2)	0.0531 (5)	0.138 (4)
C3B	0.855 (2)	0.5809 (14)	0.3534 (18)	0.0590 (7)	0.138 (4)
C2B	0.9571 (3)	0.5227 (2)	0.2371 (3)	0.0611 (6)	0.138 (4)
H3A	0.65603	0.50556	0.14672	0.0708*	0.862 (4)
H2B	0.98737	0.56293	0.16579	0.0733*	0.862 (4)
H4B	0.54131	0.47484	0.33584	0.0637*	0.862 (4)
H3B	0.77491	0.66471	0.31193	0.0708*	0.862 (4)
H4A	0.76376	0.53281	0.46218	0.0637*	0.862 (4)
H8	0.60931	−0.20752	0.11426	0.0512*
H9	0.856 (3)	0.029 (3)	0.086 (2)	0.050 (5)*
H16A	0.14149	0.06091	0.43500	0.0795*
H16B	0.21516	−0.08010	0.45319	0.0795*
H16C	0.05241	−0.11568	0.28852	0.0795*
H5	0.37662	0.22852	0.39473	0.0531*
H7	0.35612	−0.24001	0.21612	0.0532*
H2A	1.06434	0.58601	0.34358	0.0733*	0.862 (4)
H2C	1.09697	0.59042	0.28888	0.0733*	0.138 (4)
H2D	0.89345	0.53906	0.14537	0.0733*	0.138 (4)
H3C	0.80970	0.66932	0.34463	0.0708*	0.138 (4)
H3D	0.95675	0.62673	0.46174	0.0708*	0.138 (4)
H4C	0.55597	0.47686	0.27954	0.0637*	0.138 (4)
H4D	0.67683	0.50937	0.45626	0.0637*	0.138 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0577 (2)	0.0544 (2)	0.0691 (3)	0.0166 (2)	0.0349 (2)	0.0319 (2)
N9	0.0486 (6)	0.0350 (6)	0.0475 (6)	0.0156 (5)	0.0246 (5)	0.0209 (5)
C1	0.0476 (8)	0.0392 (7)	0.0458 (7)	0.0084 (6)	0.0155 (6)	0.0232 (6)
C2A	0.0759 (11)	0.0386 (8)	0.0776 (11)	0.0143 (8)	0.0367 (9)	0.0307 (7)
C3A	0.0760 (14)	0.0372 (8)	0.0728 (13)	0.0214 (9)	0.0301 (11)	0.0304 (9)
C4A	0.0659 (10)	0.0342 (7)	0.0616 (9)	0.0190 (7)	0.0300 (8)	0.0194 (6)
C4C	0.0506 (8)	0.0340 (7)	0.0432 (7)	0.0125 (6)	0.0184 (6)	0.0187 (5)
C4D	0.0474 (7)	0.0338 (6)	0.0402 (6)	0.0132 (5)	0.0179 (6)	0.0180 (5)
C5	0.0517 (8)	0.0407 (7)	0.0453 (7)	0.0181 (6)	0.0239 (6)	0.0194 (6)
C6	0.0440 (7)	0.0451 (7)	0.0416 (7)	0.0113 (6)	0.0178 (6)	0.0211 (6)
C7	0.0493 (8)	0.0363 (7)	0.0497 (7)	0.0093 (6)	0.0188 (6)	0.0226 (6)
C8	0.0504 (8)	0.0342 (6)	0.0468 (7)	0.0147 (6)	0.0206 (6)	0.0197 (5)
C8A	0.0439 (7)	0.0347 (6)	0.0389 (6)	0.0132 (5)	0.0167 (5)	0.0183 (5)
C9A	0.0481 (8)	0.0339 (6)	0.0426 (7)	0.0119 (6)	0.0174 (6)	0.0200 (5)
C16	0.0521 (9)	0.0552 (9)	0.0545 (8)	0.0109 (7)	0.0256 (7)	0.0262 (7)
C4B	0.0659 (10)	0.0342 (7)	0.0616 (9)	0.0190 (7)	0.0300 (8)	0.0194 (6)
C3B	0.0760 (14)	0.0372 (8)	0.0728 (13)	0.0214 (9)	0.0301 (11)	0.0304 (9)
C2B	0.0759 (11)	0.0386 (8)	0.0776 (11)	0.0143 (8)	0.0367 (9)	0.0307 (7)

Geometric parameters (Å, º) top

S1—C1	1.643 (2)	C7—C8	1.374 (2)
N9—C8A	1.359 (2)	C8—C8A	1.398 (3)
N9—C9A	1.380 (2)	C2A—H2A	0.9700
N9—H9	0.86 (2)	C2A—H2B	0.9700
C1—C9A	1.420 (3)	C2B—H2C	0.9700
C1—C2B	1.519 (3)	C2B—H2D	0.9700
C1—C2A	1.519 (3)	C3A—H3A	0.9700
C2A—C3A	1.508 (4)	C3A—H3B	0.9700
C2B—C3B	1.446 (15)	C3B—H3C	0.9700
C3A—C4A	1.520 (3)	C3B—H3D	0.9700
C3B—C4B	1.463 (15)	C4A—H4A	0.9700
C4A—C4C	1.498 (3)	C4A—H4B	0.9700
C4B—C4C	1.498 (3)	C4B—H4D	0.9700
C4C—C4D	1.415 (3)	C4B—H4C	0.9700
C4C—C9A	1.389 (3)	C5—H5	0.9300
C4D—C5	1.406 (3)	C7—H7	0.9300
C4D—C8A	1.422 (2)	C8—H8	0.9300
C5—C6	1.376 (3)	C16—H16C	0.9600
C6—C16	1.507 (3)	C16—H16A	0.9600
C6—C7	1.419 (2)	C16—H16B	0.9600

C8A—N9—C9A	108.73 (13)	H2A—C2A—H2B	108.00
C8A—N9—H9	127.5 (19)	C1—C2B—H2C	108.00
C9A—N9—H9	123.4 (19)	C1—C2B—H2D	108.00
S1—C1—C2B	121.48 (16)	C3B—C2B—H2C	108.00
C2A—C1—C9A	114.66 (17)	C3B—C2B—H2D	108.00
C2B—C1—C9A	114.66 (17)	H2C—C2B—H2D	107.00
S1—C1—C2A	121.48 (16)	C2A—C3A—H3B	109.00
S1—C1—C9A	123.85 (14)	C4A—C3A—H3A	109.00
C1—C2A—C3A	114.80 (19)	C2A—C3A—H3A	109.00
C1—C2B—C3B	118.3 (6)	H3A—C3A—H3B	108.00
C2A—C3A—C4A	113.5 (2)	C4A—C3A—H3B	109.00
C2B—C3B—C4B	121.0 (10)	C2B—C3B—H3D	107.00
C3A—C4A—C4C	109.36 (17)	C2B—C3B—H3C	107.00
C3B—C4B—C4C	112.2 (6)	C4B—C3B—H3D	107.00
C4B—C4C—C9A	122.29 (17)	H3C—C3B—H3D	107.00
C4B—C4C—C4D	130.69 (18)	C4B—C3B—H3C	107.00
C4A—C4C—C4D	130.69 (18)	C3A—C4A—H4A	110.00
C4A—C4C—C9A	122.29 (17)	C3A—C4A—H4B	110.00
C4D—C4C—C9A	107.01 (15)	H4A—C4A—H4B	108.00
C4C—C4D—C5	134.04 (17)	C4C—C4A—H4A	110.00
C4C—C4D—C8A	106.52 (14)	C4C—C4A—H4B	110.00
C5—C4D—C8A	119.43 (16)	C4C—C4B—H4D	109.00
C4D—C5—C6	120.16 (17)	H4C—C4B—H4D	108.00
C7—C6—C16	119.78 (17)	C3B—C4B—H4C	109.00
C5—C6—C16	121.41 (16)	C3B—C4B—H4D	109.00
C5—C6—C7	118.81 (16)	C4C—C4B—H4C	109.00
C6—C7—C8	123.03 (17)	C4D—C5—H5	120.00
C7—C8—C8A	117.67 (15)	C6—C5—H5	120.00
N9—C8A—C4D	108.52 (15)	C6—C7—H7	119.00
N9—C8A—C8	130.59 (15)	C8—C7—H7	118.00
C4D—C8A—C8	120.89 (14)	C7—C8—H8	121.00
N9—C9A—C4C	109.22 (15)	C8A—C8—H8	121.00
C1—C9A—C4C	124.73 (17)	C6—C16—H16A	109.00
N9—C9A—C1	126.04 (15)	C6—C16—H16B	109.00
C1—C2A—H2A	109.00	C6—C16—H16C	109.00
C1—C2A—H2B	109.00	H16A—C16—H16B	109.00
C3A—C2A—H2A	109.00	H16A—C16—H16C	109.00
C3A—C2A—H2B	109.00	H16B—C16—H16C	109.00

C9A—N9—C8A—C4D	−1.01 (16)	C4A—C4C—C9A—N9	−179.30 (14)
C9A—N9—C8A—C8	179.17 (15)	C4A—C4C—C9A—C1	0.7 (3)
C8A—N9—C9A—C1	−179.28 (15)	C4D—C4C—C9A—N9	−0.11 (17)
C8A—N9—C9A—C4C	0.70 (17)	C4D—C4C—C9A—C1	179.87 (15)
S1—C1—C2A—C3A	155.86 (17)	C4C—C4D—C5—C6	178.74 (17)
C9A—C1—C2A—C3A	−25.3 (3)	C8A—C4D—C5—C6	0.4 (2)
S1—C1—C9A—N9	−1.7 (2)	C4C—C4D—C8A—N9	0.93 (17)
S1—C1—C9A—C4C	178.38 (13)	C4C—C4D—C8A—C8	−179.22 (14)
C2A—C1—C9A—N9	179.56 (16)	C5—C4D—C8A—N9	179.65 (14)
C2A—C1—C9A—C4C	−0.4 (2)	C5—C4D—C8A—C8	−0.5 (2)
C1—C2A—C3A—C4A	51.1 (3)	C4D—C5—C6—C7	−0.3 (2)
C2A—C3A—C4A—C4C	−48.2 (2)	C4D—C5—C6—C16	−179.42 (15)
C3A—C4A—C4C—C4D	−155.34 (19)	C5—C6—C7—C8	0.2 (2)
C3A—C4A—C4C—C9A	23.7 (2)	C16—C6—C7—C8	179.32 (15)
C4A—C4C—C4D—C5	0.2 (3)	C6—C7—C8—C8A	−0.2 (2)
C4A—C4C—C4D—C8A	178.61 (16)	C7—C8—C8A—N9	−179.81 (15)
C9A—C4C—C4D—C5	−178.95 (17)	C7—C8—C8A—C4D	0.4 (2)
C9A—C4C—C4D—C8A	−0.50 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···S1ⁱ	0.86 (2)	2.77 (3)	3.4955 (15)	143 (2)

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NS
M_r	215.31
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.0846 (4), 9.5287 (7), 9.6384 (6)
α, β, γ (°)	115.009 (7), 104.901 (6), 98.074 (6)
V (Å³)	546.28 (8)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.31
Crystal size (mm)	0.46 × 0.28 × 0.21

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.609, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3471, 2102, 1924
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.133, 1.06
No. of reflections	2102
No. of parameters	145
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···S1ⁱ	0.86 (2)	2.77 (3)	3.4955 (15)	143 (2)

Symmetry code: (i) −x+2, −y, −z.

Acknowledgements

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

References

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