2-(4-Amino­phen­yl)-1,3-benzothia­zole

Zhang, Y.; Su, Z.-H.; Wang, Q.-Z.; Teng, L.

doi:10.1107/S1600536808031565

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2065

doi:10.1107/S1600536808031565

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2-(4-Aminophenyl)-1,3-benzothiazole

Yong Zhang,^a ^* Zhen-Hong Su,^b Qing-Zhi Wang ^b and Lei Teng ^a

^aSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China, and ^bMedical School, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: zy0340907@yahoo.com.cn

(Received 5 September 2008; accepted 30 September 2008; online 4 October 2008)

The title compound, C₁₃H₁₀N₂S, contains two independent molecules in its asymmetric unit, with slightly different conformations. In one molecule, the dihedral angle between the benzothiazole unit and the benzene ring is 6.73 (1)°, while the corresponding angle in the other molecule is 1.8 (1)°. In the crystal structure, the molecules are linked into layers by N—H⋯N hydrogen bonds.

Related literature

For background concerning the medical applications of benzothiazole compounds, see: Alfred & Sawhney (1968 ); Hutchinson & Jennings (2002 ).

Experimental

Crystal data

C₁₃H₁₀N₂S
M_r = 226.29
Triclinic, $[P \overline 1]$
a = 8.7038 (5) Å
b = 9.5933 (6) Å
c = 14.5144 (9) Å
α = 70.720 (1)°
β = 77.326 (1)°
γ = 73.170 (1)°
V = 1084.63 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.924, T_max = 0.948
6984 measured reflections
4199 independent reflections
3123 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.115
S = 0.97
4199 reflections
301 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯N4ⁱ	0.819 (15)	2.644 (18)	3.374 (3)	149 (2)
N1—H1A⋯N3ⁱⁱ	0.850 (15)	2.324 (16)	3.145 (3)	163 (2)
Symmetry codes: (i) x+1, y, z-1; (ii) x, y, z-1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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/S1600536808031565/bi2301sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031565/bi2301Isup2.hkl

checkCIF report

Comment top

Benzothiazole derivatives that contain five-membered sulfur-containing heterocyclic rings have been drawing great attention due to their antimalarial and antitumor properties (Alfred & Sawhney, 1968; Hutchinson & Jennings, 2002). Our research group is trying to prepare some benzothiazoles to find new antitumor compounds. In this context, we have crystallized the title compound and report its crystal structure.

Related literature top

For background concerning the medical applications of benzothiazole compounds, see: Alfred & Sawhney (1968); Hutchinson & Jennings (2002).

Experimental top

All reagents and solvents were used as obtained without further purification. 4-Aminobenzoic acid (13.7 g, 0.1 mol) and 2-aminothiophenol (12.5 g, 0.1 mmol) were mixed together with polyphosphoric acid (50 g) and heated to 493 K under an N₂ atmosphere for 4 h. The reaction mixture was cooled to room temperature and poured into 10% K₂CO₃(aq) solution. The precipitate was filtered under reduced pressure. Yellow crystals were obtained by recrystallization from methanol. Yield: 90%. Elemental analysis calculated: C 69.03, H 4.42, N 12.39 %; found: C 69.01, H 4.48, N 12.41 %.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 two independent molecules in the title compound. Displacement ellipsoids are drawn at the 50% probability level for non-H atoms.
	Fig. 2. Packing diagram showing molecules linked by N—H···N hydrogen bonds (dashed lines) into layers in the (001) planes.

2-(4-Aminophenyl)-1,3-benzothiazole top

Crystal data top

C₁₃H₁₀N₂S	Z = 4
M_r = 226.29	F(000) = 472
Triclinic, P1	D_x = 1.386 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7038 (5) Å	Cell parameters from 2375 reflections
b = 9.5933 (6) Å	θ = 2.3–26.3°
c = 14.5144 (9) Å	µ = 0.27 mm⁻¹
α = 70.720 (1)°	T = 298 K
β = 77.326 (1)°	Block, blue
γ = 73.170 (1)°	0.30 × 0.20 × 0.20 mm
V = 1084.63 (11) Å³

Data collection top

Bruker SMART CCD diffractometer	4199 independent reflections
Radiation source: fine-focus sealed tube	3123 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
T_min = 0.924, T_max = 0.948	k = −11→10
6984 measured reflections	l = −17→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.0596P)²] where P = (F_o² + 2F_c²)/3
4199 reflections	(Δ/σ)_max = 0.001
301 parameters	Δρ_max = 0.29 e Å⁻³
4 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₃H₁₀N₂S	γ = 73.170 (1)°
M_r = 226.29	V = 1084.63 (11) Å³
Triclinic, P1	Z = 4
a = 8.7038 (5) Å	Mo Kα radiation
b = 9.5933 (6) Å	µ = 0.27 mm⁻¹
c = 14.5144 (9) Å	T = 298 K
α = 70.720 (1)°	0.30 × 0.20 × 0.20 mm
β = 77.326 (1)°

Data collection top

Bruker SMART CCD diffractometer	4199 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3123 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.948	R_int = 0.036
6984 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.29 e Å⁻³
4199 reflections	Δρ_min = −0.23 e Å⁻³
301 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	0.1360 (2)	0.6101 (2)	0.06950 (16)	0.0440 (5)
C2	0.0112 (3)	0.7409 (3)	0.05957 (19)	0.0611 (7)
H2	−0.0368	0.7833	0.0022	0.073*
C3	−0.0402 (3)	0.8066 (3)	0.1348 (2)	0.0679 (7)
H3	−0.1234	0.8943	0.1282	0.081*
C4	0.0296 (3)	0.7447 (3)	0.2208 (2)	0.0634 (7)
H4	−0.0078	0.7912	0.2711	0.076*
C5	0.1539 (3)	0.6151 (3)	0.23330 (18)	0.0558 (6)
H5	0.2007	0.5736	0.2911	0.067*
C6	0.2066 (2)	0.5488 (2)	0.15651 (15)	0.0427 (5)
C7	0.3187 (2)	0.4164 (2)	0.02866 (14)	0.0380 (5)
C8	0.4141 (2)	0.3129 (2)	−0.02870 (14)	0.0372 (5)
C9	0.3726 (2)	0.3255 (2)	−0.11916 (15)	0.0449 (5)
H9	0.2833	0.4002	−0.1424	0.054*
C10	0.4606 (3)	0.2302 (2)	−0.17460 (15)	0.0451 (5)
H10	0.4295	0.2408	−0.2344	0.054*
C11	0.5958 (2)	0.1178 (2)	−0.14273 (15)	0.0390 (5)
C12	0.6382 (2)	0.1045 (2)	−0.05262 (16)	0.0452 (5)
H12	0.7282	0.0304	−0.0297	0.054*
C13	0.5487 (2)	0.1994 (2)	0.00275 (15)	0.0427 (5)
H13	0.5788	0.1876	0.0630	0.051*
C14	0.6126 (2)	0.2440 (2)	0.53255 (15)	0.0429 (5)
C15	0.7512 (3)	0.2790 (3)	0.54271 (18)	0.0551 (6)
H15	0.8010	0.2299	0.5992	0.066*
C16	0.8130 (3)	0.3879 (3)	0.4673 (2)	0.0613 (7)
H16	0.9060	0.4119	0.4731	0.074*
C17	0.7399 (3)	0.4625 (3)	0.3830 (2)	0.0638 (7)
H17	0.7843	0.5357	0.3332	0.077*
C18	0.6027 (3)	0.4301 (3)	0.37176 (18)	0.0601 (7)
H18	0.5535	0.4800	0.3151	0.072*
C19	0.5396 (3)	0.3201 (2)	0.44794 (16)	0.0461 (5)
C20	0.4087 (2)	0.1299 (2)	0.57195 (14)	0.0386 (5)
C21	0.3035 (2)	0.0279 (2)	0.62886 (14)	0.0386 (5)
C22	0.3356 (3)	−0.0669 (2)	0.72208 (15)	0.0467 (5)
H22	0.4236	−0.0635	0.7472	0.056*
C23	0.2405 (2)	−0.1649 (2)	0.77762 (16)	0.0483 (5)
H23	0.2650	−0.2269	0.8396	0.058*
C24	0.1078 (2)	−0.1729 (2)	0.74244 (16)	0.0440 (5)
C25	0.0748 (3)	−0.0791 (2)	0.64972 (16)	0.0487 (5)
H25	−0.0134	−0.0824	0.6248	0.058*
C26	0.1713 (3)	0.0188 (2)	0.59423 (16)	0.0464 (5)
H26	0.1472	0.0802	0.5321	0.056*
N1	0.6820 (2)	0.0234 (2)	−0.19862 (15)	0.0554 (5)
N2	0.20084 (19)	0.53292 (18)	−0.00148 (12)	0.0436 (4)
N3	0.5371 (2)	0.13608 (18)	0.60184 (12)	0.0433 (4)
N4	0.0104 (3)	−0.2687 (3)	0.80188 (16)	0.0600 (6)
S1	0.35999 (7)	0.39025 (6)	0.14764 (4)	0.04624 (18)
S2	0.36992 (7)	0.25484 (6)	0.45569 (4)	0.05063 (19)
H1A	0.655 (3)	0.035 (3)	−0.2540 (13)	0.061*
H1B	0.754 (2)	−0.048 (2)	−0.1747 (16)	0.061*
H4A	−0.038 (3)	−0.292 (3)	0.7646 (15)	0.061*
H4B	0.052 (3)	−0.339 (2)	0.8488 (15)	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0389 (12)	0.0461 (12)	0.0501 (14)	−0.0118 (10)	0.0011 (10)	−0.0207 (10)
C2	0.0518 (14)	0.0641 (15)	0.0686 (17)	0.0027 (12)	−0.0137 (12)	−0.0309 (13)
C3	0.0492 (14)	0.0746 (18)	0.086 (2)	0.0000 (13)	−0.0046 (14)	−0.0468 (16)
C4	0.0532 (15)	0.0781 (17)	0.0731 (18)	−0.0155 (13)	0.0060 (13)	−0.0494 (15)
C5	0.0573 (15)	0.0649 (15)	0.0536 (15)	−0.0189 (12)	−0.0015 (12)	−0.0279 (12)
C6	0.0395 (12)	0.0474 (12)	0.0452 (13)	−0.0169 (10)	0.0010 (10)	−0.0170 (10)
C7	0.0390 (11)	0.0404 (11)	0.0366 (11)	−0.0167 (9)	−0.0025 (9)	−0.0089 (9)
C8	0.0369 (11)	0.0370 (11)	0.0377 (11)	−0.0124 (9)	−0.0014 (9)	−0.0101 (9)
C9	0.0441 (12)	0.0447 (12)	0.0411 (12)	−0.0027 (10)	−0.0088 (10)	−0.0110 (10)
C10	0.0524 (13)	0.0480 (12)	0.0342 (12)	−0.0072 (10)	−0.0096 (10)	−0.0127 (10)
C11	0.0380 (11)	0.0385 (11)	0.0412 (12)	−0.0124 (9)	0.0004 (9)	−0.0128 (9)
C12	0.0408 (12)	0.0438 (11)	0.0485 (13)	−0.0029 (9)	−0.0113 (10)	−0.0130 (10)
C13	0.0450 (12)	0.0459 (12)	0.0395 (12)	−0.0110 (10)	−0.0099 (10)	−0.0123 (10)
C14	0.0477 (12)	0.0369 (11)	0.0430 (13)	−0.0072 (10)	−0.0016 (10)	−0.0154 (10)
C15	0.0570 (14)	0.0537 (14)	0.0592 (15)	−0.0143 (12)	−0.0062 (12)	−0.0222 (12)
C16	0.0586 (15)	0.0556 (14)	0.0763 (19)	−0.0214 (12)	0.0015 (14)	−0.0275 (14)
C17	0.0738 (18)	0.0478 (14)	0.0643 (17)	−0.0206 (13)	0.0050 (14)	−0.0128 (12)
C18	0.0688 (17)	0.0495 (14)	0.0535 (15)	−0.0147 (12)	−0.0028 (13)	−0.0066 (12)
C19	0.0495 (13)	0.0382 (11)	0.0469 (13)	−0.0054 (10)	−0.0010 (10)	−0.0152 (10)
C20	0.0432 (12)	0.0385 (11)	0.0330 (11)	−0.0027 (9)	−0.0038 (9)	−0.0155 (9)
C21	0.0401 (11)	0.0398 (11)	0.0358 (11)	−0.0049 (9)	−0.0019 (9)	−0.0167 (9)
C22	0.0422 (12)	0.0530 (13)	0.0462 (13)	−0.0136 (10)	−0.0106 (10)	−0.0108 (10)
C23	0.0478 (13)	0.0527 (13)	0.0420 (13)	−0.0140 (10)	−0.0092 (10)	−0.0064 (10)
C24	0.0391 (12)	0.0446 (12)	0.0490 (13)	−0.0067 (10)	−0.0006 (10)	−0.0203 (10)
C25	0.0426 (12)	0.0585 (14)	0.0534 (14)	−0.0124 (10)	−0.0099 (11)	−0.0243 (11)
C26	0.0494 (13)	0.0520 (13)	0.0379 (12)	−0.0059 (10)	−0.0100 (10)	−0.0156 (10)
N1	0.0568 (13)	0.0576 (12)	0.0497 (13)	0.0022 (10)	−0.0113 (10)	−0.0237 (11)
N2	0.0417 (10)	0.0446 (10)	0.0435 (10)	−0.0072 (8)	−0.0050 (8)	−0.0145 (8)
N3	0.0491 (11)	0.0456 (10)	0.0366 (10)	−0.0102 (8)	−0.0058 (8)	−0.0143 (8)
N4	0.0548 (13)	0.0675 (14)	0.0621 (15)	−0.0266 (11)	−0.0061 (11)	−0.0147 (11)
S1	0.0501 (3)	0.0474 (3)	0.0425 (3)	−0.0087 (3)	−0.0085 (3)	−0.0156 (2)
S2	0.0553 (4)	0.0491 (3)	0.0427 (3)	−0.0094 (3)	−0.0117 (3)	−0.0062 (3)

Geometric parameters (Å, º) top

C1—N2	1.391 (3)	C15—C16	1.375 (3)
C1—C2	1.391 (3)	C15—H15	0.930
C1—C6	1.399 (3)	C16—C17	1.384 (3)
C2—C3	1.367 (3)	C16—H16	0.930
C2—H2	0.930	C17—C18	1.372 (3)
C3—C4	1.383 (3)	C17—H17	0.930
C3—H3	0.930	C18—C19	1.392 (3)
C4—C5	1.380 (3)	C18—H18	0.930
C4—H4	0.930	C19—S2	1.732 (2)
C5—C6	1.390 (3)	C20—N3	1.307 (2)
C5—H5	0.930	C20—C21	1.460 (3)
C6—S1	1.730 (2)	C20—S2	1.7543 (19)
C7—N2	1.305 (2)	C21—C26	1.388 (3)
C7—C8	1.461 (3)	C21—C22	1.393 (3)
C7—S1	1.763 (2)	C22—C23	1.370 (3)
C8—C13	1.390 (3)	C22—H22	0.930
C8—C9	1.395 (3)	C23—C24	1.392 (3)
C9—C10	1.371 (3)	C23—H23	0.930
C9—H9	0.930	C24—N4	1.383 (3)
C10—C11	1.391 (3)	C24—C25	1.387 (3)
C10—H10	0.930	C25—C26	1.377 (3)
C11—N1	1.366 (3)	C25—H25	0.930
C11—C12	1.392 (3)	C26—H26	0.930
C12—C13	1.371 (3)	N1—H1B	0.819 (15)
C12—H12	0.930	N1—H1A	0.850 (15)
C13—H13	0.930	N4—H4A	0.869 (15)
C14—C19	1.388 (3)	N4—H4B	0.844 (15)
C14—N3	1.390 (3)	S1—S2	4.2373 (8)
C14—C15	1.391 (3)

N2—C1—C2	125.4 (2)	C15—C16—H16	119.3
N2—C1—C6	115.50 (18)	C17—C16—H16	119.3
C2—C1—C6	119.1 (2)	C18—C17—C16	121.0 (2)
C3—C2—C1	119.5 (2)	C18—C17—H17	119.5
C3—C2—H2	120.3	C16—C17—H17	119.5
C1—C2—H2	120.3	C17—C18—C19	117.8 (2)
C2—C3—C4	121.0 (2)	C17—C18—H18	121.1
C2—C3—H3	119.5	C19—C18—H18	121.1
C4—C3—H3	119.5	C14—C19—C18	121.6 (2)
C5—C4—C3	121.3 (2)	C14—C19—S2	109.70 (16)
C5—C4—H4	119.4	C18—C19—S2	128.71 (19)
C3—C4—H4	119.4	N3—C20—C21	123.87 (18)
C4—C5—C6	117.7 (2)	N3—C20—S2	114.84 (15)
C4—C5—H5	121.1	C21—C20—S2	121.30 (15)
C6—C5—H5	121.1	C26—C21—C22	117.29 (19)
C5—C6—C1	121.5 (2)	C26—C21—C20	123.02 (18)
C5—C6—S1	129.30 (18)	C22—C21—C20	119.69 (18)
C1—C6—S1	109.24 (16)	C23—C22—C21	121.5 (2)
N2—C7—C8	124.89 (18)	C23—C22—H22	119.2
N2—C7—S1	114.76 (15)	C21—C22—H22	119.2
C8—C7—S1	120.34 (14)	C22—C23—C24	120.8 (2)
C13—C8—C9	117.06 (19)	C22—C23—H23	119.6
C13—C8—C7	122.61 (18)	C24—C23—H23	119.6
C9—C8—C7	120.33 (17)	N4—C24—C25	122.4 (2)
C10—C9—C8	121.48 (18)	N4—C24—C23	119.4 (2)
C10—C9—H9	119.3	C25—C24—C23	118.1 (2)
C8—C9—H9	119.3	C26—C25—C24	120.7 (2)
C9—C10—C11	120.95 (19)	C26—C25—H25	119.7
C9—C10—H10	119.5	C24—C25—H25	119.7
C11—C10—H10	119.5	C25—C26—C21	121.5 (2)
N1—C11—C10	120.28 (19)	C25—C26—H26	119.2
N1—C11—C12	121.75 (18)	C21—C26—H26	119.2
C10—C11—C12	117.97 (19)	C11—N1—H1B	117.7 (17)
C13—C12—C11	120.69 (19)	C11—N1—H1A	120.2 (16)
C13—C12—H12	119.7	H1B—N1—H1A	122 (2)
C11—C12—H12	119.7	C7—N2—C1	110.94 (17)
C12—C13—C8	121.86 (19)	C20—N3—C14	110.98 (17)
C12—C13—H13	119.1	C24—N4—H4A	108.7 (16)
C8—C13—H13	119.1	C24—N4—H4B	116.1 (17)
C19—C14—N3	115.20 (19)	H4A—N4—H4B	118 (2)
C19—C14—C15	119.69 (19)	C6—S1—C7	89.56 (10)
N3—C14—C15	125.1 (2)	C6—S1—S2	90.73 (7)
C16—C15—C14	118.5 (2)	C7—S1—S2	164.85 (6)
C16—C15—H15	120.8	C19—S2—C20	89.27 (10)
C14—C15—H15	120.8	C19—S2—S1	95.40 (7)
C15—C16—C17	121.4 (2)	C20—S2—S1	157.02 (7)

N2—C1—C2—C3	−179.3 (2)	S2—C20—C21—C22	−178.30 (15)
C6—C1—C2—C3	−0.2 (3)	C26—C21—C22—C23	−0.2 (3)
C1—C2—C3—C4	−0.2 (4)	C20—C21—C22—C23	−179.62 (19)
C2—C3—C4—C5	0.3 (4)	C21—C22—C23—C24	0.0 (3)
C3—C4—C5—C6	0.0 (4)	C22—C23—C24—N4	−177.5 (2)
C4—C5—C6—C1	−0.4 (3)	C22—C23—C24—C25	0.1 (3)
C4—C5—C6—S1	178.68 (17)	N4—C24—C25—C26	177.6 (2)
N2—C1—C6—C5	179.73 (18)	C23—C24—C25—C26	0.1 (3)
C2—C1—C6—C5	0.5 (3)	C24—C25—C26—C21	−0.4 (3)
N2—C1—C6—S1	0.5 (2)	C22—C21—C26—C25	0.4 (3)
C2—C1—C6—S1	−178.76 (17)	C20—C21—C26—C25	179.80 (19)
N2—C7—C8—C13	173.49 (18)	C8—C7—N2—C1	−179.01 (17)
S1—C7—C8—C13	−5.9 (3)	S1—C7—N2—C1	0.4 (2)
N2—C7—C8—C9	−6.2 (3)	C2—C1—N2—C7	178.6 (2)
S1—C7—C8—C9	174.43 (15)	C6—C1—N2—C7	−0.6 (3)
C13—C8—C9—C10	0.0 (3)	C21—C20—N3—C14	−179.77 (17)
C7—C8—C9—C10	179.73 (18)	S2—C20—N3—C14	0.5 (2)
C8—C9—C10—C11	−0.5 (3)	C19—C14—N3—C20	−0.5 (3)
C9—C10—C11—N1	179.81 (19)	C15—C14—N3—C20	179.33 (19)
C9—C10—C11—C12	0.4 (3)	C5—C6—S1—C7	−179.4 (2)
N1—C11—C12—C13	−179.2 (2)	C1—C6—S1—C7	−0.23 (15)
C10—C11—C12—C13	0.2 (3)	C5—C6—S1—S2	15.8 (2)
C11—C12—C13—C8	−0.7 (3)	C1—C6—S1—S2	−165.07 (14)
C9—C8—C13—C12	0.6 (3)	N2—C7—S1—C6	−0.08 (15)
C7—C8—C13—C12	−179.14 (18)	C8—C7—S1—C6	179.33 (16)
C19—C14—C15—C16	−0.7 (3)	N2—C7—S1—S2	91.1 (3)
N3—C14—C15—C16	179.4 (2)	C8—C7—S1—S2	−89.5 (3)
C14—C15—C16—C17	0.4 (3)	C14—C19—S2—C20	0.00 (15)
C15—C16—C17—C18	−0.1 (4)	C18—C19—S2—C20	179.6 (2)
C16—C17—C18—C19	0.1 (4)	C14—C19—S2—S1	−157.47 (14)
N3—C14—C19—C18	−179.35 (19)	C18—C19—S2—S1	22.1 (2)
C15—C14—C19—C18	0.8 (3)	N3—C20—S2—C19	−0.31 (16)
N3—C14—C19—S2	0.3 (2)	C21—C20—S2—C19	179.97 (17)
C15—C14—C19—S2	−179.57 (16)	N3—C20—S2—S1	101.9 (2)
C17—C18—C19—C14	−0.5 (3)	C21—C20—S2—S1	−77.8 (2)
C17—C18—C19—S2	179.95 (18)	C6—S1—S2—C19	−101.16 (9)
N3—C20—C21—C26	−177.40 (18)	C7—S1—S2—C19	167.8 (3)
S2—C20—C21—C26	2.3 (3)	C6—S1—S2—C20	157.87 (19)
N3—C20—C21—C22	2.0 (3)	C7—S1—S2—C20	66.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···N4ⁱ	0.82 (2)	2.64 (2)	3.374 (3)	149 (2)
N1—H1A···N3ⁱⁱ	0.85 (2)	2.32 (2)	3.145 (3)	163 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N₂S
M_r	226.29
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.7038 (5), 9.5933 (6), 14.5144 (9)
α, β, γ (°)	70.720 (1), 77.326 (1), 73.170 (1)
V (Å³)	1084.63 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.924, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	6984, 4199, 3123
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.115, 0.97
No. of reflections	4199
No. of parameters	301
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···N4ⁱ	0.819 (15)	2.644 (18)	3.374 (3)	149 (2)
N1—H1A···N3ⁱⁱ	0.850 (15)	2.324 (16)	3.145 (3)	163 (2)

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

References

Alfred, B. & Sawhney, S. N. (1968). J. Med. Chem. 11, 270–273. PubMed Web of Science Google Scholar
Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hutchinson, I. & Jennings, S. A. (2002). J. Med. Chem. 45, 744–747. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 11| November 2008| Page o2065

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