N-Benzyl­thieno[3,2-d]pyrimidin-4-amine

Štarha, P.; Trávníček, Z.

doi:10.1107/S1600536813009537

organic compounds

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Volume 69| Part 5| May 2013| Page o698

https://doi.org/10.1107/S1600536813009537

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N-Benzylthieno[3,2-d]pyrimidin-4-amine

Pavel Štarha ^a and Zdeněk Trávníček ^a ^*

^aDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, CZ-771 46 Olomouc, Czech Republic
^*Correspondence e-mail: zdenek.travnicek@upol.cz

(Received 3 April 2013; accepted 8 April 2013; online 13 April 2013)

The title compound, C₁₃H₁₁N₃S, crystallizes with two independent molecules in the asymmetric unit. The two molecules are geometrically very similar and differ mainly in a spatial orientation of the benzene and thieno[3,2-d]pyrimidine ring systems [dihedral angles = 69.49 (4) and 79.05 (3)°]. The nine-membered thieno[3,2-d]pyrimidine moieties have a planar conformation (r.m.s. deviations = 0.020 and 0.012 Å). In the crystal, molecules are linked through N—H⋯N, N—H⋯C and C—H⋯π non-covalent contacts into chains along the c axis, while neighbouring chains are connected via C—H⋯N interactions.

Related literature

For the synthesis of 4-benzylaminothieno[3,2-d]pyrimidine hydrochloride, its NMR characterization (DMSO-d₆ solution) and biological activity, see: Crespo et al. (1998 ).

Experimental

Crystal data

C₁₃H₁₁N₃S
M_r = 241.31
Monoclinic, P 2₁ /c
a = 19.3430 (4) Å
b = 9.46296 (16) Å
c = 12.8221 (2) Å
β = 94.3231 (17)°
V = 2340.30 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 K
0.40 × 0.40 × 0.25 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.905, T_max = 0.939
19406 measured reflections
4109 independent reflections
3528 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.078
S = 1.07
4109 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N1ⁱ	0.88	2.13	2.999 (2)	167
N4A—H4A⋯N1Aⁱⁱ	0.88	2.05	2.872 (2)	156
C7—H7⋯Cgⁱⁱⁱ	0.95	2.58	3.5317 (13)	175
C2A—H2A⋯N3^iv	0.95	2.67	3.527 (2)	150
C15—H15⋯N3A	0.95	2.58	3.4842 (18)	159
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); 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: DIAMOND (Brandenburg, 2011 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813009537/tk5215sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009537/tk5215Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009537/tk5215Isup3.cml

checkCIF report

Comment top

The essentially planar thieno[3,2-d]pyrimidine moiety is formed by six-membered (pyrimidine) and five-membered (thiophene) rings, which form a dihedral angle of 2.53 (4)° and 1.24 (4)° (for the molecule with the N1 and N1A atoms, respectively). The thieno[3,2-d]pyrimidine moiety is substituted by benzylamine at the C4 position (Fig. 1). The dihedral angles formed by the benzene and thieno[3,2-d]pyrimidine rings is 69.49 (4)° for the N1-molecule, and 79.05 (3)° for the N1A-molecule. The N4—H4···N1ⁱ (for the molecule with the N1 atom) and N4A—H4A···N1Aⁱⁱ (for the molecule with the N1A atom) hydrogen bonds together with other non-covalent contacts of the type N—H···C and C—H···π (Fig. 2, Table 1) connect the individual molecules into chains along the c axis (symmetry codes: i) x, –y+0.5, z+0.5; ii) x, –y+1.5, z–0.5). The neighbouring chains are connected through the C15–H15···N3A and and C2A—H2A···N3 interactions.

Related literature top

For the synthesis of 4-benzylaminothieno[3,2-d]pyrimidine hydrochloride, its NMR characterization (DMSO-d₆ solution) and biological activity, see: Crespo et al. (1998).

Experimental top

4-Chlorothieno[3,2-d]pyrimidine (10.0 mmol) was dissolved in 50 ml of 2-propanol. Benzylamine (13.0 mmol) and triethylamine (16.0 mmol) were subsequently added to the reaction mixture, which was stirred at 60 °C. The TLC control showed one spot after 18 h. After that, the mixture was evaporated and suspended in distilled water (20 ml). The product was collected by filtration, washed with distilled water and 2-propanol and dried in a desiccator over silica gel. Part of the product was recrystallized from acetone, which led to a crystalline product containing the crystals suitable for a single-crystal X-ray analysis. ¹H NMR (DMF-d₇, TMS, 298 K, p.p.m.): δ 8.52 (s, 1H, HC²), 8.41 (t, J = 6.5 Hz, 1H, HN⁴), 8.14 (d, J = 5.3 Hz, 1H, HC⁶), 7.44 (d, J = 7.7 Hz, 2H, HC^11,15), 7.42 (d, J = 5.5 Hz, 1H, HC⁷), 7.33 (t, J = 7.7 Hz, 2H, HC^12,14), 7.25 (t, J = 7.5 Hz, 1H, HC¹³), 4.87 (d, J = 6.0 Hz, 2H, HC⁹). ¹³C NMR (DMF-d₇, TMS, 298 K, p.p.m.): δ 160.6 (C^7`), 158.0 (C⁴), 155.4 (C²), 140.6 (C¹⁰), 133.2 (C⁶), 129.0 (C^12,14), 128.2 (C^11,15), 127.5 (C¹³), 125.4 (C⁷), 115.8 (C^4`), 44.5 (C⁹). Analysis calculated for C₁₃H₁₁N₃S₁: C 64.7, H 4.6, N 17.4, S 13.3%; found: C 64.3, H 4.6, N 17.3, S 12.8%. Elemental analysis (C, H, N) was performed on a Thermo Scientific Flash 2000 CHNO-S Analyzer. The ¹H and ¹³C NMR spectra (DMF-d₇ solutions, calibrated against tetramethylsilane) were collected at 298 K on a Varian 400 spectrometer at 400.00 and 100.58 MHz, respectively.

Structure description top

For the synthesis of 4-benzylaminothieno[3,2-d]pyrimidine hydrochloride, its NMR characterization (DMSO-d₆ solution) and biological activity, see: Crespo et al. (1998).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Two crystallographically independent molecules of the title compound with the non-hydrogen atoms depicted with anisotropic displacement ellipsoids at the 50% probability level and given with the atom numbering scheme.
	Fig. 2. Part of the crystal structure, showing the formation of one-dimensional chains as well as non-covalent ineteractions within (N4—H4···N1 hydrogen bond (dashed green lines) and C7—H7···π, N4A—H4A···C2A (dashed orange lines)) and between (C15–H15···N3A and C2A—H2A···N3; dashed orange lines; see Table 1 for parameters) the chains.

N-Benzylthieno[3,2-d]pyrimidin-4-amine top

Crystal data top

C₁₃H₁₁N₃S	F(000) = 1008
M_r = 241.31	D_x = 1.370 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15514 reflections
a = 19.3430 (4) Å	θ = 3.0–33.2°
b = 9.46296 (16) Å	µ = 0.26 mm⁻¹
c = 12.8221 (2) Å	T = 120 K
β = 94.3231 (17)°	Prism, colourless
V = 2340.30 (7) Å³	0.40 × 0.40 × 0.25 mm
Z = 8

Data collection top

Agilent Xcalibur Sapphire2 diffractometer	4109 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3528 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 8.3611 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scans	h = −23→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −11→11
T_min = 0.905, T_max = 0.939	l = −15→15
19406 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0476P)² + 0.4186P] where P = (F_o² + 2F_c²)/3
4109 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₃H₁₁N₃S	V = 2340.30 (7) Å³
M_r = 241.31	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.3430 (4) Å	µ = 0.26 mm⁻¹
b = 9.46296 (16) Å	T = 120 K
c = 12.8221 (2) Å	0.40 × 0.40 × 0.25 mm
β = 94.3231 (17)°

Data collection top

Agilent Xcalibur Sapphire2 diffractometer	4109 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3528 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.939	R_int = 0.019
19406 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.07	Δρ_max = 0.28 e Å⁻³
4109 reflections	Δρ_min = −0.25 e Å⁻³
307 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
S5	0.108822 (18)	0.10694 (4)	0.60102 (3)	0.02112 (11)
S5A	0.45872 (2)	0.62119 (4)	0.66155 (3)	0.03086 (12)
N3A	0.31415 (6)	0.88825 (12)	0.75775 (9)	0.0224 (3)
N3	0.19707 (6)	0.41535 (12)	0.44021 (8)	0.0206 (3)
C2A	0.33340 (8)	0.87296 (15)	0.85980 (11)	0.0248 (3)
H2A	0.3066	0.9241	0.9062	0.030*
C2	0.19194 (7)	0.34543 (15)	0.34913 (10)	0.0223 (3)
H2	0.2092	0.3942	0.2917	0.027*
N1A	0.38455 (6)	0.79651 (13)	0.90461 (9)	0.0271 (3)
N1	0.16633 (6)	0.21820 (12)	0.32771 (8)	0.0222 (3)
C7A'	0.42113 (7)	0.72184 (14)	0.83595 (11)	0.0227 (3)
C7'	0.14191 (7)	0.15142 (14)	0.41194 (10)	0.0186 (3)
C4A'	0.40431 (7)	0.72635 (14)	0.72891 (11)	0.0204 (3)
C4'	0.14582 (7)	0.21307 (14)	0.51077 (10)	0.0174 (3)
N4	0.18145 (6)	0.41308 (12)	0.61780 (8)	0.0198 (3)
H4	0.1750	0.3622	0.6737	0.024*
N4A	0.33088 (6)	0.82477 (13)	0.58732 (9)	0.0238 (3)
H4A	0.3504	0.7673	0.5443	0.029*
C4	0.17530 (6)	0.34889 (14)	0.52409 (10)	0.0170 (3)
C4A	0.34922 (7)	0.81394 (14)	0.68957 (10)	0.0193 (3)
C7A	0.47914 (8)	0.63230 (16)	0.86262 (13)	0.0323 (4)
H7A	0.4982	0.6165	0.9321	0.039*
C7	0.10891 (7)	0.01643 (15)	0.41142 (10)	0.0221 (3)
H7	0.1017	−0.0415	0.3511	0.026*
C6A	0.50344 (8)	0.57307 (18)	0.77755 (13)	0.0373 (4)
H6A	0.5419	0.5103	0.7809	0.045*
C6	0.08920 (7)	−0.01926 (15)	0.50635 (11)	0.0232 (3)
H6	0.0666	−0.1058	0.5199	0.028*
C9	0.19815 (7)	0.56162 (15)	0.63204 (11)	0.0232 (3)
H9A	0.2132	0.6007	0.5658	0.028*
H9B	0.2371	0.5716	0.6862	0.028*
C9A	0.28012 (7)	0.92695 (16)	0.54290 (11)	0.0275 (3)
H9D	0.2434	0.9403	0.5917	0.033*
H9C	0.2581	0.8894	0.4764	0.033*
C10A	0.31332 (7)	1.06765 (16)	0.52284 (11)	0.0264 (3)
C10	0.13638 (7)	0.64490 (14)	0.66460 (10)	0.0194 (3)
C11	0.06933 (7)	0.60827 (14)	0.62788 (11)	0.0227 (3)
H11	0.0622	0.5333	0.5790	0.027*
C11A	0.32231 (7)	1.16842 (17)	0.60148 (12)	0.0297 (3)
H11A	0.3050	1.1508	0.6676	0.036*
C12A	0.35621 (8)	1.29412 (17)	0.58469 (13)	0.0344 (4)
H12A	0.3618	1.3624	0.6390	0.041*
C12	0.01270 (8)	0.68002 (15)	0.66191 (12)	0.0285 (3)
H12	−0.0329	0.6538	0.6364	0.034*
C13	0.02237 (8)	0.78964 (15)	0.73294 (12)	0.0291 (3)
H13	−0.0164	0.8380	0.7570	0.035*
C13A	0.38197 (8)	1.32031 (18)	0.48879 (13)	0.0360 (4)
H13A	0.4061	1.4057	0.4776	0.043*
C14	0.08889 (8)	0.82823 (15)	0.76859 (11)	0.0265 (3)
H14	0.0959	0.9042	0.8167	0.032*
C14A	0.37252 (9)	1.22257 (19)	0.40976 (13)	0.0388 (4)
H14A	0.3895	1.2412	0.3435	0.047*
C15A	0.33837 (8)	1.09711 (18)	0.42644 (12)	0.0328 (4)
H15A	0.3320	1.0302	0.3713	0.039*
C15	0.14548 (7)	0.75657 (14)	0.73447 (11)	0.0228 (3)
H15	0.1910	0.7842	0.7592	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S5	0.0280 (2)	0.01963 (19)	0.01620 (18)	−0.00222 (13)	0.00445 (14)	0.00056 (13)
S5A	0.0272 (2)	0.0318 (2)	0.0339 (2)	0.00627 (15)	0.00492 (16)	−0.00622 (16)
N3A	0.0211 (6)	0.0247 (6)	0.0218 (6)	0.0000 (5)	0.0039 (5)	−0.0010 (5)
N3	0.0206 (6)	0.0243 (6)	0.0169 (6)	−0.0002 (5)	0.0024 (5)	0.0031 (5)
C2A	0.0263 (8)	0.0272 (8)	0.0217 (7)	−0.0011 (6)	0.0061 (6)	−0.0019 (6)
C2	0.0221 (7)	0.0294 (8)	0.0158 (7)	0.0000 (6)	0.0033 (5)	0.0041 (6)
N1A	0.0291 (7)	0.0310 (7)	0.0212 (6)	−0.0007 (5)	0.0017 (5)	0.0004 (5)
N1	0.0233 (6)	0.0271 (7)	0.0163 (6)	0.0019 (5)	0.0027 (5)	0.0012 (5)
C7A'	0.0219 (7)	0.0210 (7)	0.0252 (7)	−0.0047 (5)	0.0004 (6)	0.0020 (6)
C7'	0.0168 (7)	0.0225 (7)	0.0165 (7)	0.0055 (5)	0.0012 (5)	0.0008 (5)
C4A'	0.0185 (7)	0.0186 (7)	0.0244 (7)	−0.0039 (5)	0.0046 (5)	−0.0011 (6)
C4'	0.0162 (7)	0.0198 (7)	0.0163 (6)	0.0048 (5)	0.0018 (5)	0.0018 (5)
N4	0.0260 (6)	0.0182 (6)	0.0155 (6)	−0.0013 (5)	0.0037 (5)	0.0004 (5)
N4A	0.0262 (6)	0.0262 (7)	0.0191 (6)	0.0014 (5)	0.0020 (5)	−0.0008 (5)
C4	0.0137 (6)	0.0205 (7)	0.0168 (7)	0.0047 (5)	0.0010 (5)	0.0014 (5)
C4A	0.0176 (7)	0.0198 (7)	0.0206 (7)	−0.0062 (5)	0.0029 (5)	0.0000 (6)
C7A	0.0294 (8)	0.0327 (9)	0.0334 (9)	0.0006 (7)	−0.0069 (7)	0.0046 (7)
C7	0.0253 (7)	0.0220 (7)	0.0186 (7)	0.0034 (6)	−0.0009 (6)	−0.0042 (6)
C6A	0.0272 (9)	0.0331 (9)	0.0505 (11)	0.0095 (7)	−0.0028 (7)	0.0015 (8)
C6	0.0257 (8)	0.0191 (7)	0.0247 (7)	−0.0002 (6)	0.0003 (6)	−0.0014 (6)
C9	0.0240 (8)	0.0222 (7)	0.0239 (7)	−0.0042 (6)	0.0050 (6)	−0.0033 (6)
C9A	0.0221 (8)	0.0361 (9)	0.0237 (7)	0.0012 (6)	−0.0027 (6)	0.0028 (6)
C10A	0.0176 (7)	0.0332 (8)	0.0280 (8)	0.0066 (6)	−0.0013 (6)	0.0080 (7)
C10	0.0238 (7)	0.0174 (7)	0.0173 (7)	−0.0019 (5)	0.0033 (5)	0.0040 (5)
C11	0.0281 (8)	0.0181 (7)	0.0213 (7)	−0.0005 (6)	−0.0015 (6)	0.0008 (6)
C11A	0.0234 (8)	0.0353 (9)	0.0307 (8)	0.0056 (6)	0.0036 (6)	0.0045 (7)
C12A	0.0296 (9)	0.0320 (9)	0.0413 (10)	0.0048 (7)	0.0009 (7)	0.0031 (7)
C12	0.0239 (8)	0.0245 (8)	0.0367 (9)	0.0009 (6)	−0.0007 (6)	0.0057 (7)
C13	0.0315 (9)	0.0209 (8)	0.0360 (8)	0.0064 (6)	0.0105 (7)	0.0058 (6)
C13A	0.0299 (9)	0.0316 (9)	0.0465 (10)	0.0038 (7)	0.0026 (7)	0.0133 (8)
C14	0.0398 (9)	0.0161 (7)	0.0245 (8)	−0.0010 (6)	0.0078 (6)	−0.0002 (6)
C14A	0.0365 (9)	0.0459 (10)	0.0344 (9)	0.0039 (8)	0.0050 (7)	0.0172 (8)
C15A	0.0330 (9)	0.0384 (9)	0.0266 (8)	0.0055 (7)	0.0000 (7)	0.0067 (7)
C15	0.0275 (8)	0.0190 (7)	0.0218 (7)	−0.0055 (6)	0.0025 (6)	0.0016 (6)

Geometric parameters (Å, º) top

S5—C6	1.7246 (14)	C6A—H6A	0.9500
S5—C4'	1.7277 (13)	C6—H6	0.9500
S5A—C6A	1.7245 (17)	C9—C10	1.5159 (19)
S5A—C4A'	1.7266 (14)	C9—H9A	0.9900
N3A—C2A	1.3410 (19)	C9—H9B	0.9900
N3A—C4A	1.3447 (18)	C9A—C10A	1.509 (2)
N3—C2	1.3395 (18)	C9A—H9D	0.9900
N3—C4	1.3408 (17)	C9A—H9C	0.9900
C2A—N1A	1.3216 (19)	C10A—C11A	1.389 (2)
C2A—H2A	0.9500	C10A—C15A	1.389 (2)
C2—N1	1.3228 (19)	C10—C15	1.3880 (19)
C2—H2	0.9500	C10—C11	1.390 (2)
N1A—C7A'	1.3671 (19)	C11—C12	1.387 (2)
N1—C7'	1.3660 (17)	C11—H11	0.9500
C7A'—C4A'	1.387 (2)	C11A—C12A	1.383 (2)
C7A'—C7A	1.427 (2)	C11A—H11A	0.9500
C7'—C4'	1.3918 (18)	C12A—C13A	1.383 (2)
C7'—C7	1.428 (2)	C12A—H12A	0.9500
C4A'—C4A	1.4127 (19)	C12—C13	1.384 (2)
C4'—C4	1.4112 (19)	C12—H12	0.9500
N4—C4	1.3436 (17)	C13—C14	1.382 (2)
N4—C9	1.4507 (18)	C13—H13	0.9500
N4—H4	0.8800	C13A—C14A	1.374 (2)
N4A—C4A	1.3361 (17)	C13A—H13A	0.9500
N4A—C9A	1.4626 (18)	C14—C15	1.386 (2)
N4A—H4A	0.8800	C14—H14	0.9500
C7A—C6A	1.342 (2)	C14A—C15A	1.383 (2)
C7A—H7A	0.9500	C14A—H14A	0.9500
C7—C6	1.3457 (19)	C15A—H15A	0.9500
C7—H7	0.9500	C15—H15	0.9500

C6—S5—C4'	90.65 (6)	N4—C9—C10	111.45 (11)
C6A—S5A—C4A'	90.33 (7)	N4—C9—H9A	109.3
C2A—N3A—C4A	117.47 (12)	C10—C9—H9A	109.3
C2—N3—C4	117.42 (12)	N4—C9—H9B	109.3
N1A—C2A—N3A	128.83 (13)	C10—C9—H9B	109.3
N1A—C2A—H2A	115.6	H9A—C9—H9B	108.0
N3A—C2A—H2A	115.6	N4A—C9A—C10A	111.58 (11)
N1—C2—N3	129.24 (13)	N4A—C9A—H9D	109.3
N1—C2—H2	115.4	C10A—C9A—H9D	109.3
N3—C2—H2	115.4	N4A—C9A—H9C	109.3
C2A—N1A—C7A'	114.19 (12)	C10A—C9A—H9C	109.3
C2—N1—C7'	113.79 (11)	H9D—C9A—H9C	108.0
N1A—C7A'—C4A'	121.81 (13)	C11A—C10A—C15A	118.36 (15)
N1A—C7A'—C7A	126.04 (13)	C11A—C10A—C9A	120.90 (13)
C4A'—C7A'—C7A	112.15 (13)	C15A—C10A—C9A	120.68 (14)
N1—C7'—C4'	121.84 (13)	C15—C10—C11	118.57 (13)
N1—C7'—C7	126.25 (12)	C15—C10—C9	120.62 (12)
C4'—C7'—C7	111.89 (12)	C11—C10—C9	120.78 (12)
C7A'—C4A'—C4A	119.06 (12)	C12—C11—C10	120.68 (13)
C7A'—C4A'—S5A	111.77 (11)	C12—C11—H11	119.7
C4A—C4A'—S5A	129.15 (11)	C10—C11—H11	119.7
C7'—C4'—C4	119.06 (12)	C12A—C11A—C10A	120.81 (14)
C7'—C4'—S5	111.67 (10)	C12A—C11A—H11A	119.6
C4—C4'—S5	129.22 (10)	C10A—C11A—H11A	119.6
C4—N4—C9	123.67 (11)	C11A—C12A—C13A	119.95 (16)
C4—N4—H4	118.2	C11A—C12A—H12A	120.0
C9—N4—H4	118.2	C13A—C12A—H12A	120.0
C4A—N4A—C9A	123.62 (12)	C13—C12—C11	120.22 (14)
C4A—N4A—H4A	118.2	C13—C12—H12	119.9
C9A—N4A—H4A	118.2	C11—C12—H12	119.9
N3—C4—N4	119.55 (12)	C14—C13—C12	119.49 (14)
N3—C4—C4'	118.59 (12)	C14—C13—H13	120.3
N4—C4—C4'	121.85 (12)	C12—C13—H13	120.3
N4A—C4A—N3A	119.21 (12)	C14A—C13A—C12A	119.88 (16)
N4A—C4A—C4A'	122.19 (12)	C14A—C13A—H13A	120.1
N3A—C4A—C4A'	118.60 (12)	C12A—C13A—H13A	120.1
C6A—C7A—C7A'	111.74 (14)	C13—C14—C15	120.26 (14)
C6A—C7A—H7A	124.1	C13—C14—H14	119.9
C7A'—C7A—H7A	124.1	C15—C14—H14	119.9
C6—C7—C7'	112.17 (12)	C13A—C14A—C15A	120.15 (16)
C6—C7—H7	123.9	C13A—C14A—H14A	119.9
C7'—C7—H7	123.9	C15A—C14A—H14A	119.9
C7A—C6A—S5A	114.02 (12)	C14A—C15A—C10A	120.83 (16)
C7A—C6A—H6A	123.0	C14A—C15A—H15A	119.6
S5A—C6A—H6A	123.0	C10A—C15A—H15A	119.6
C7—C6—S5	113.61 (11)	C14—C15—C10	120.76 (13)
C7—C6—H6	123.2	C14—C15—H15	119.6
S5—C6—H6	123.2	C10—C15—H15	119.6

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1ⁱ	0.88	2.13	2.999 (2)	167
N4A—H4A···N1Aⁱⁱ	0.88	2.05	2.872 (2)	156
C7—H7···Cgⁱⁱⁱ	0.95	2.58	3.5317 (13)	175
C2A—H2A···N3^iv	0.95	2.67	3.527 (2)	150
C15—H15···N3A	0.95	2.58	3.4842 (18)	159

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃S
M_r	241.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	19.3430 (4), 9.46296 (16), 12.8221 (2)
β (°)	94.3231 (17)
V (Å³)	2340.30 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.40 × 0.40 × 0.25

Data collection
Diffractometer	Agilent Xcalibur Sapphire2
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.905, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	19406, 4109, 3528
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.078, 1.07
No. of reflections	4109
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2011), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1ⁱ	0.88	2.13	2.999 (2)	167
N4A—H4A···N1Aⁱⁱ	0.88	2.05	2.872 (2)	156
C7—H7···Cgⁱⁱⁱ	0.95	2.58	3.5317 (13)	175
C2A—H2A···N3^iv	0.95	2.67	3.527 (2)	150
C15—H15···N3A	0.95	2.58	3.4842 (18)	159

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) x, −y+3/2, z+1/2.

Acknowledgements

This work was supported by Palacký University (grant No. PrF_2013_015). The authors wish to thank Dr Igor Popa for performing NMR experiments and Mr Tomáš Šilha for performing CHN elemental analysis.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Crespo, M. I., Pagés, L., Vega, A., Segarra, V., López, M., Doménech, T., Miralpeix, M., Beleta, J., Ryder, H. & Palacios, J. M. (1998). J. Med. Chem. 41, 4021–4035. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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