2,2′-(Sulfanediyldimethyl­ene)bis­(1,3-benzothia­zole)

Strasser, C.E.; Jongh, L.-A. de; Raubenheimer, H.G.; Cronje, S.

doi:10.1107/S1600536811004478

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o622

doi:10.1107/S1600536811004478

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2,2′-(Sulfanediyldimethylene)bis(1,3-benzothiazole)

Christoph E. Strasser,^a Leigh-Anne de Jongh,^a Helgard G. Raubenheimer ^a and Stephanie Cronje ^a ^*

^aDepartment of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland 7602, South Africa
^*Correspondence e-mail: scron@sun.ac.za

(Received 17 January 2011; accepted 6 February 2011; online 12 February 2011)

In the title compound, C₁₆H₁₂N₂S₃, the two benzothiazole groups are oriented differently with respect to the –CH₂– groups, one being approximately staggered and one nearly eclipsed. A sulfur–π interaction of 3.3627 (11) Å is observed between the bridging thioether S atom and a thiazole ring. The crystal packing is further stabilized by intermolecular C—H⋯N and C—H⋯π interactions.

Related literature

For the preparation of the title compound, see: Rai & Braunwarth (1961 ). For a related structure, see: Clegg & Elsegood (2005 ). For S⋯π interactions, see: Singh et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₂N₂S₃
M_r = 328.46
Triclinic, $[P \overline 1]$
a = 6.3714 (10) Å
b = 7.8748 (13) Å
c = 15.339 (3) Å
α = 78.616 (3)°
β = 89.537 (3)°
γ = 74.707 (3)°
V = 727.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 100 K
0.15 × 0.13 × 0.13 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.809, T_max = 0.938
8237 measured reflections
2942 independent reflections
2584 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.088
S = 1.05
2942 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3—C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯N1ⁱ	0.99	2.57	3.519 (3)	161
C13—H13⋯N2ⁱⁱ	0.95	2.61	3.441 (3)	146
C1—H1A⋯Cg1ⁱⁱⁱ	0.99	2.75	3.650 (2)	?
C9—H9A⋯Cg1^iv	0.99	2.84	3.610 (3)	?
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1; (iv) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ; Atwood & Barbour, 2003 ); software used to prepare material for publication: X-SEED and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004478/zq2087sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004478/zq2087Isup2.hkl

checkCIF report

Comment top

Within the benzothiazole rings of the title compound (Fig. 1) no differences are observed in bond lengths and angles. In the bridge, however, the values for the two S—C—C angles [107.72 (13)° and 113.74 (14)°] and S—C bonds [1.823 (2) and 1.803 (2) Å] differ significantly. This deviation may be explained with the two different S3—C—C—S torsion angles of 71.44 (17) and 27.1 (2)° of the respective benzothiazolyl moieties.

A related structure where one benzothiazole and one benzimidazole moiety is present was determined by Clegg & Elsegood (2005). The arrangement of the molecule in this structure is similar to the one determined here, albeit the orientation of the heterocycles with respect to the CH₂ groups is more uniform [values for the S1—C9—C10—N3(H) and S1—C1—C2—S2 torsion angles -90.6 (7)° and -69.4 (6)°, respectively].

Interactions between neighbouring molecules in the title compound are summarized in Table 1. They include two unique C—H···N contacts between H1B and N1ⁱ [symmetry code (i) –x + 2, –y + 1, –z + 1] as well as between H13 and N2ⁱⁱ [symmetry code (ii) x – 1, y, z], leading to columns of associated molecules running parallel to the crystallographic a axis. The hydrogen atoms H1A and H9A of the CH₂ groups are furthermore engaged in C—H···π interactions with benzo groups at distances of 2.75 Å [H1A···Cg1ⁱⁱⁱ, (iii) –x + 1, –y + 1, –z + 1] and 2.84 Å [H9A···Cg1^iv, (iv) –x + 2, –y, –z + 1] [C1···Cg1ⁱⁱⁱ 3.650 (2) Å, C9···Cg1^iv 3.610 (3) Å].

An offset parallel thiazole ring stacking [centroid distance Cg2···Cg2ⁱⁱⁱ 3.6724 (12) Å] of the rings containing S1 related by a centre of inversion is also found. Finally, a S···π interaction is observed between S3 and the thiazole ring containing S1, the S3···Cg2^iv distance is 3.3627 (11) Å which is shorter than the thione S···π interaction (3.631 Å) found in the solid state of 5-(2-chloroethyl)-6-methyl-2-thiouracil (Singh et al., 2006).

Related literature top

For the preparation of the title compound, see: Rai & Braunwarth (1961). For a related structure, see: Clegg & Elsegood (2005). For S···π interactions, see: Singh et al. (2006).

Experimental top

The compound was synthesized from 2,2'-thiodiethanoic acid and o-aminothiophenol as described in the literature procedure for the preparation of 2,2'-[thiobis(ethylene)]bis(benzo-1,3-thiazole) (Rai & Braunwarth, 1961).

NMR (CD₂Cl₂): ¹H (400 MHz): δ 7.95 (m, 2 H), 7.87 (m, 2 H), 7.47 (m, 2 H), 7.38 (m, 2 H), 4.24 (s, 4 H, CH₂) p.p.m.; ¹³C{¹H} (101 MHz): δ 169.0, 153.8, 136.4, 126.6, 125.7, 123.5, 122.2, 34.4 p.p.m.

MS (ESI): m/z (intensity) 332.0331 (2%, C₁₅¹³CH₁₃N₂S₂³⁴S⁺ calcd. 332.0227), 331.0282 (15, C₁₆H₁₃N₂S₂³⁴S⁺ calcd. 331.0193), 330.0335 (18, C₁₅¹³CH₁₃N₂S₃⁺ calcd. 330.0270), 329.0242 (100, C₁₆H₁₃N₂S₃⁺ calcd. 329.0235), 295.0449 (4, C₁₆H₁₁N₂S₂⁺ calcd. 295.0358).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: X-SEED (Barbour, 2001; Atwood & Barbour, 2003) and PLATON (Spek, 2009).

Figures top

Fig. 1. The asymmetric unit of the title compound. Ellipsoids are drawn at the 50% probability level.

2,2'-(Sulfanediyldimethylene)bis(1,3-benzothiazole) top

Crystal data top

C₁₆H₁₂N₂S₃	Z = 2
M_r = 328.46	F(000) = 340
Triclinic, P1	D_x = 1.500 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3714 (10) Å	Cell parameters from 2489 reflections
b = 7.8748 (13) Å	θ = 2.7–26.3°
c = 15.339 (3) Å	µ = 0.50 mm⁻¹
α = 78.616 (3)°	T = 100 K
β = 89.537 (3)°	Prism, colourless
γ = 74.707 (3)°	0.15 × 0.13 × 0.13 mm
V = 727.0 (2) Å³

Data collection top

Bruker APEX CCD area-detector diffractometer	2942 independent reflections
Radiation source: fine-focus sealed tube	2584 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 26.4°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
T_min = 0.809, T_max = 0.938	k = −9→9
8237 measured reflections	l = −19→19

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0441P)² + 0.3246P] where P = (F_o² + 2F_c²)/3
2942 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₁₂N₂S₃	γ = 74.707 (3)°
M_r = 328.46	V = 727.0 (2) Å³
Triclinic, P1	Z = 2
a = 6.3714 (10) Å	Mo Kα radiation
b = 7.8748 (13) Å	µ = 0.50 mm⁻¹
c = 15.339 (3) Å	T = 100 K
α = 78.616 (3)°	0.15 × 0.13 × 0.13 mm
β = 89.537 (3)°

Data collection top

Bruker APEX CCD area-detector diffractometer	2942 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2584 reflections with I > 2σ(I)
T_min = 0.809, T_max = 0.938	R_int = 0.028
8237 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.05	Δρ_max = 0.37 e Å⁻³
2942 reflections	Δρ_min = −0.21 e Å⁻³
190 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 > 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
S1	0.53975 (8)	0.21565 (6)	0.51882 (3)	0.01656 (13)
N1	0.7847 (3)	0.3908 (2)	0.42435 (10)	0.0151 (3)
C1	0.9069 (3)	0.2967 (3)	0.58191 (13)	0.0172 (4)
H1A	0.8209	0.3306	0.6328	0.021*
H1B	1.0025	0.3779	0.5661	0.021*
S2	0.82962 (8)	0.06186 (7)	0.79611 (3)	0.01754 (14)
N2	1.1321 (3)	0.1947 (2)	0.84450 (11)	0.0168 (4)
C2	0.7589 (3)	0.3120 (2)	0.50442 (13)	0.0146 (4)
S3	1.07030 (8)	0.06391 (6)	0.61145 (3)	0.01686 (13)
C3	0.6238 (3)	0.3805 (2)	0.36660 (13)	0.0154 (4)
C4	0.4736 (3)	0.2891 (2)	0.40572 (12)	0.0155 (4)
C5	0.3029 (3)	0.2694 (3)	0.35627 (14)	0.0192 (4)
H5	0.2021	0.2076	0.3834	0.023*
C6	0.2851 (3)	0.3430 (3)	0.26593 (14)	0.0222 (5)
H6	0.1697	0.3317	0.2306	0.027*
C7	0.4337 (3)	0.4336 (3)	0.22579 (13)	0.0207 (4)
H7	0.4178	0.4823	0.1637	0.025*
C8	0.6032 (3)	0.4535 (3)	0.27507 (13)	0.0190 (4)
H8	0.7035	0.5153	0.2475	0.023*
C9	1.2192 (3)	0.0752 (3)	0.70864 (13)	0.0189 (4)
H9A	1.3282	−0.0417	0.7291	0.023*
H9B	1.2992	0.1681	0.6919	0.023*
C10	1.0779 (3)	0.1183 (3)	0.78436 (12)	0.0161 (4)
C11	0.9748 (3)	0.2116 (3)	0.90792 (13)	0.0163 (4)
C12	0.7962 (3)	0.1475 (3)	0.89280 (12)	0.0160 (4)
C13	0.6216 (3)	0.1623 (3)	0.94854 (13)	0.0197 (4)
H13	0.4992	0.1214	0.9367	0.024*
C14	0.6321 (3)	0.2384 (3)	1.02160 (13)	0.0212 (4)
H14	0.5158	0.2489	1.0610	0.025*
C15	0.8112 (3)	0.3003 (3)	1.03843 (13)	0.0218 (4)
H15	0.8152	0.3514	1.0893	0.026*
C16	0.9823 (3)	0.2883 (3)	0.98216 (13)	0.0201 (4)
H16	1.1031	0.3314	0.9937	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0170 (3)	0.0169 (3)	0.0167 (2)	−0.0062 (2)	0.00418 (18)	−0.00351 (19)
N1	0.0156 (8)	0.0127 (8)	0.0178 (8)	−0.0045 (7)	0.0012 (6)	−0.0040 (6)
C1	0.0226 (10)	0.0131 (9)	0.0165 (10)	−0.0057 (8)	−0.0003 (8)	−0.0034 (8)
S2	0.0194 (3)	0.0194 (3)	0.0163 (2)	−0.0091 (2)	−0.00021 (19)	−0.00424 (19)
N2	0.0154 (8)	0.0172 (8)	0.0172 (8)	−0.0037 (7)	−0.0014 (6)	−0.0029 (7)
C2	0.0154 (9)	0.0108 (9)	0.0188 (10)	−0.0038 (8)	0.0024 (7)	−0.0058 (7)
S3	0.0175 (3)	0.0159 (3)	0.0170 (3)	−0.00225 (19)	−0.00110 (19)	−0.00597 (19)
C3	0.0156 (10)	0.0105 (9)	0.0190 (10)	−0.0010 (8)	0.0006 (8)	−0.0042 (7)
C4	0.0157 (10)	0.0129 (9)	0.0170 (9)	−0.0016 (8)	0.0025 (7)	−0.0042 (8)
C5	0.0143 (10)	0.0152 (10)	0.0271 (11)	−0.0013 (8)	0.0010 (8)	−0.0053 (8)
C6	0.0218 (11)	0.0158 (10)	0.0278 (11)	0.0002 (8)	−0.0069 (9)	−0.0084 (9)
C7	0.0260 (11)	0.0144 (10)	0.0181 (10)	0.0009 (8)	−0.0047 (8)	−0.0027 (8)
C8	0.0229 (11)	0.0151 (10)	0.0180 (10)	−0.0040 (8)	0.0023 (8)	−0.0029 (8)
C9	0.0158 (10)	0.0230 (11)	0.0177 (10)	−0.0032 (8)	−0.0012 (8)	−0.0065 (8)
C10	0.0156 (10)	0.0139 (9)	0.0169 (10)	−0.0029 (8)	−0.0029 (8)	0.0001 (8)
C11	0.0158 (10)	0.0130 (9)	0.0177 (10)	−0.0023 (8)	−0.0022 (8)	0.0007 (8)
C12	0.0195 (10)	0.0129 (9)	0.0150 (9)	−0.0051 (8)	−0.0022 (8)	−0.0003 (7)
C13	0.0191 (10)	0.0201 (10)	0.0197 (10)	−0.0086 (8)	0.0006 (8)	0.0006 (8)
C14	0.0211 (11)	0.0219 (11)	0.0187 (10)	−0.0042 (9)	0.0039 (8)	−0.0016 (8)
C15	0.0250 (11)	0.0212 (11)	0.0184 (10)	−0.0030 (9)	−0.0013 (8)	−0.0067 (8)
C16	0.0205 (10)	0.0192 (10)	0.0219 (10)	−0.0061 (9)	−0.0024 (8)	−0.0064 (8)

Geometric parameters (Å, º) top

S1—C4	1.7346 (19)	C6—C7	1.399 (3)
S1—C2	1.7503 (19)	C6—H6	0.9500
N1—C2	1.292 (2)	C7—C8	1.383 (3)
N1—C3	1.389 (2)	C7—H7	0.9500
C1—C2	1.489 (3)	C8—H8	0.9500
C1—S3	1.823 (2)	C9—C10	1.501 (3)
C1—H1A	0.9900	C9—H9A	0.9900
C1—H1B	0.9900	C9—H9B	0.9900
S2—C12	1.736 (2)	C11—C16	1.397 (3)
S2—C10	1.751 (2)	C11—C12	1.399 (3)
N2—C10	1.291 (3)	C12—C13	1.392 (3)
N2—C11	1.390 (2)	C13—C14	1.381 (3)
S3—C9	1.803 (2)	C13—H13	0.9500
C3—C8	1.401 (3)	C14—C15	1.398 (3)
C3—C4	1.406 (3)	C14—H14	0.9500
C4—C5	1.390 (3)	C15—C16	1.380 (3)
C5—C6	1.386 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500

C4—S1—C2	88.91 (9)	C7—C8—H8	120.7
C2—N1—C3	110.15 (16)	C3—C8—H8	120.7
C2—C1—S3	107.72 (13)	C10—C9—S3	113.74 (14)
C2—C1—H1A	110.2	C10—C9—H9A	108.8
S3—C1—H1A	110.2	S3—C9—H9A	108.8
C2—C1—H1B	110.2	C10—C9—H9B	108.8
S3—C1—H1B	110.2	S3—C9—H9B	108.8
H1A—C1—H1B	108.5	H9A—C9—H9B	107.7
C12—S2—C10	88.55 (9)	N2—C10—C9	122.79 (18)
C10—N2—C11	110.20 (17)	N2—C10—S2	116.52 (15)
N1—C2—C1	123.58 (17)	C9—C10—S2	120.68 (15)
N1—C2—S1	116.45 (15)	N2—C11—C16	125.20 (18)
C1—C2—S1	119.96 (14)	N2—C11—C12	115.28 (17)
C9—S3—C1	99.65 (9)	C16—C11—C12	119.52 (18)
N1—C3—C8	124.87 (17)	C13—C12—C11	121.76 (18)
N1—C3—C4	115.51 (17)	C13—C12—S2	128.76 (16)
C8—C3—C4	119.62 (18)	C11—C12—S2	109.43 (14)
C5—C4—C3	121.90 (18)	C14—C13—C12	117.83 (19)
C5—C4—S1	129.11 (15)	C14—C13—H13	121.1
C3—C4—S1	108.99 (14)	C12—C13—H13	121.1
C6—C5—C4	117.59 (18)	C13—C14—C15	121.05 (19)
C6—C5—H5	121.2	C13—C14—H14	119.5
C4—C5—H5	121.2	C15—C14—H14	119.5
C5—C6—C7	121.29 (19)	C16—C15—C14	120.97 (19)
C5—C6—H6	119.4	C16—C15—H15	119.5
C7—C6—H6	119.4	C14—C15—H15	119.5
C8—C7—C6	121.10 (19)	C15—C16—C11	118.84 (19)
C8—C7—H7	119.5	C15—C16—H16	120.6
C6—C7—H7	119.5	C11—C16—H16	120.6
C7—C8—C3	118.51 (18)

C3—N1—C2—C1	178.89 (17)	C1—S3—C9—C10	64.24 (16)
C3—N1—C2—S1	0.4 (2)	C11—N2—C10—C9	−177.69 (17)
S3—C1—C2—N1	−106.97 (19)	C11—N2—C10—S2	1.1 (2)
S3—C1—C2—S1	71.44 (17)	S3—C9—C10—N2	−154.18 (16)
C4—S1—C2—N1	−0.29 (16)	S3—C9—C10—S2	27.1 (2)
C4—S1—C2—C1	−178.80 (16)	C12—S2—C10—N2	−0.75 (16)
C2—C1—S3—C9	−176.45 (13)	C12—S2—C10—C9	178.10 (16)
C2—N1—C3—C8	179.46 (18)	C10—N2—C11—C16	179.98 (19)
C2—N1—C3—C4	−0.4 (2)	C10—N2—C11—C12	−1.0 (2)
N1—C3—C4—C5	179.49 (17)	N2—C11—C12—C13	−177.23 (17)
C8—C3—C4—C5	−0.4 (3)	C16—C11—C12—C13	1.8 (3)
N1—C3—C4—S1	0.2 (2)	N2—C11—C12—S2	0.5 (2)
C8—C3—C4—S1	−179.68 (15)	C16—C11—C12—S2	179.54 (15)
C2—S1—C4—C5	−179.21 (19)	C10—S2—C12—C13	177.61 (19)
C2—S1—C4—C3	0.05 (14)	C10—S2—C12—C11	0.12 (14)
C3—C4—C5—C6	0.2 (3)	C11—C12—C13—C14	−1.8 (3)
S1—C4—C5—C6	179.35 (15)	S2—C12—C13—C14	−179.05 (16)
C4—C5—C6—C7	0.1 (3)	C12—C13—C14—C15	0.7 (3)
C5—C6—C7—C8	−0.3 (3)	C13—C14—C15—C16	0.4 (3)
C6—C7—C8—C3	0.1 (3)	C14—C15—C16—C11	−0.5 (3)
N1—C3—C8—C7	−179.63 (17)	N2—C11—C16—C15	178.31 (18)
C4—C3—C8—C7	0.2 (3)	C12—C11—C16—C15	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3—C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N1ⁱ	0.99	2.57	3.519 (3)	161
C13—H13···N2ⁱⁱ	0.95	2.61	3.441 (3)	146
C1—H1A···Cg1ⁱⁱⁱ	0.99	2.75	3.650 (2)	?
C9—H9A···Cg1^iv	0.99	2.84	3.610 (3)	?

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂S₃
M_r	328.46
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.3714 (10), 7.8748 (13), 15.339 (3)
α, β, γ (°)	78.616 (3), 89.537 (3), 74.707 (3)
V (Å³)	727.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.15 × 0.13 × 0.13

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.809, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	8237, 2942, 2584
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.088, 1.05
No. of reflections	2942
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.21

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001; Atwood & Barbour, 2003) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3—C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N1ⁱ	0.99	2.57	3.519 (3)	161
C13—H13···N2ⁱⁱ	0.95	2.61	3.441 (3)	146
C1—H1A···Cg1ⁱⁱⁱ	0.99	2.75	3.650 (2)	?
C9—H9A···Cg1^iv	0.99	2.84	3.610 (3)	?

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

Acknowledgements

We would like to thank the National Research Foundation (NRF) of South Africa for financial support.

References

Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth Des. 3, 3–8. Web of Science CrossRef CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2002). SADABS and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Clegg, W. & Elsegood, M. R. J. (2005). Private communication (refcode: SAWTOA). CCDC, Cambridge, England. Google Scholar
Rai, C. & Braunwarth, J. B. (1961). J. Org. Chem. 26, 3434–3436. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, F. V., Kumar, R., Sharon, A., Broder, C. K., Howard, J. A. K., Goel, A. & Maulik, P. R. (2006). J. Mol. Struct. 782, 55–59. Web of Science CSD CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 3| March 2011| Page o622

doi:10.1107/S1600536811004478

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