2-Phenyl-5,6,7,8-tetra­hydro­imidazo[2,1-b][1,3]benzo­thia­zole

Bunev, A.S.; Sukhonosova, E.V.; Purygin, P.P.; Ostapenko, G.I.; Khrustalev, V.N.

doi:10.1107/S1600536814010885

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o668

doi:10.1107/S1600536814010885

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2-Phenyl-5,6,7,8-tetrahydroimidazo[2,1-b][1,3]benzothiazole

Alexander S. Bunev,^a ^* Elena V. Sukhonosova,^b Petr P. Purygin,^b Gennady I. Ostapenko ^a and Victor N. Khrustalev ^c

^aDepartment of Chemistry and Chemical Technology, Togliatti State University, 14 Belorusskaya St, Togliatti 445667, Russian Federation, ^bDepartment of Organic, Bioorganic and Medicinal Chemistry, Samara State University, 1 Akademician Pavlov St, Samara 443011, Russian Federation, and ^cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B–334, Moscow 119991, Russian Federation
^*Correspondence e-mail: a.s.bunev@gmail.com

(Received 5 May 2014; accepted 12 May 2014; online 17 May 2014)

The title compound, C₁₅H₁₄N₂S, crystallizes with two independent molecules in the asymmetric unit. The central imidazo[2,1-b][1,3]benzothiazole unit is planar (r.m.s. deviations of 0.010 and 0.008 Å for the two independent molecules). The fused tetrahydrohexane ring adopts a half-chair conformation. The phenyl substituent is twisted by 16.96 (13) and 22.89 (12)° relative to the central imidazo[2,1-b][1,3]benzothiazole unit in the two molecules. In the crystal, there are no significant intermolecular interactions present.

CCDC reference: 1002491

Related literature

For applications of imidazo[2,1-b][1,3]benzothiazoles, see: Ager et al. (1988 ); Sanfilippo et al. (1988 ); Barchéchath et al. (2005 ); Andreani et al. (2008 ); Chao et al. (2009 ); Kumbhare et al. (2011 ); Chandak et al. (2013 ). For the crystal structures of related compounds, see: Landreau et al. (2002 ); Adib et al. (2008 ); Fun, Asik et al. (2011 ); Fun, Hemamalini et al. (2011 ); Ghabbour et al. (2012 ); Bunev et al. (2013a ,b , 2014 ).

Experimental

Crystal data

C₁₅H₁₄N₂S
M_r = 254.34
Monoclinic, P 2₁ /n
a = 12.523 (3) Å
b = 10.699 (3) Å
c = 18.930 (5) Å
β = 102.291 (6)°
V = 2478.2 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 120 K
0.30 × 0.05 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.931, T_max = 0.993
33479 measured reflections
7558 independent reflections
3223 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.157
S = 0.93
7558 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1002491

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814010885/rk2428sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010885/rk2428Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010885/rk2428Isup3.cml

checkCIF report

Comment top

Imidazo[2,1-b][1,3]benzothiazole are of great interest due to their biological properties. These compounds and their derivatives demonstrate the antitumor (Andreani et al., 2008), antiallergic (Ager et al., 1988), anesthetic (Sanfilippo et al., 1988) and anti-cancer (Kumbhare et al., 2011) activities as well as the inhibition activity of apoptosis in testiculargerm cells (Chandak et al., 2013), lymphocytes (Barchéchath et al., 2005), and FMS-like tyrosine kinase-3 (FLT3) (Chao et al., 2009).

In this work, a 5,6,7,8-tetrahydroimidazo[2,1-b][1,3]benzothiazole, C₁₅H₁₄N₂S, (I) was prepared by the reaction of 5,6,7,8-tetrahydrobenzothiazole-2-amine with 2-bromo-1-phenylethanone (Fig. 1), and its structure was unambiguously established by the X-ray diffraction study (Fig. 2).

The bond lengths and angles within the molecule of I are in a good agreement with those found in the related compounds (Landreau et al., 2002; Adib et al., 2008; Fun, Asik et al., 2011; Fun, Hemamalini et al., 2011; Ghabbour et al., 2012; Bunev et al., 2013a,b; Bunev et al., 2014).

The title compound, C₁₅H₁₄N₂S (I), crystallizes with two crystallographically independent molecules in the asymmetric unit (Fig. 2). The central imidazo[2,1-b][1,3]benzothiazole moiety is planar (r.m.s. deviation = 0.010 and 0.008 Å, respectively, for the two crystallographically independent molecules). The fused tetrahydrohexane ring adopts a half-chair conformation (the C6, C7 and C21, C22 carbon atoms are out of the planes passed through the other atoms of the rings by 0.411 (6), -0.314 (6) and 0.387 (6), -0.355 (6) Å, respectively, for the two crystallographically independent molecules). The phenyl substituent is twisted by 16.96 (13) and 22.89 (12) ° (for the two crystallographically independent molecules, respectively) relative to the central imidazo[2,1-b][1,3]benzothiazole moiety.

In the crystal, the molecules of I are arrangement at van der Waals distances.

Related literature top

For applications of imidazo[2,1-b][1,3]benzothiazoles, see: Ager et al. (1988); Sanfilippo et al. (1988); Barchéchath et al. (2005); Andreani et al. (2008); Chao et al. (2009); Kumbhare et al. (2011); Chandak et al. (2013). For the crystal structures of related compounds, see: Landreau et al. (2002); Adib et al. (2008); Fun, Asik et al. (2011); Fun, Hemamalini et al. (2011); Ghabbour et al. (2012); Bunev et al. (2013a,b, 2014).

Experimental top

A mixture of 5,6,7,8-tetrahydrobenzothiazole–2–amine (1.54 g, 10 mmol) and 2–bromo–1–phenylethanone (1.99 g, 10 mmol) was dissolved in acetone (35 mL). The reaction mixture was stirred for 24 h. The resulting precipitate was collected, suspended in EtOH (50 mL) containing 6N HCl (5 mL) and heated under reflux. After cooling up to room temperature, the solution basified with 20% NH₄OH yielded the expected 5,6,7,8–tetrahydroimidazo[2,1–b][1,3]benzothiazole. The crude product was crystallized from EtOH. Yield is 82%. The single crystals of the product were obtained by slow crystallization from EtOH. M.p. = 440–442 K. IR (KBr), ν/cm^-1: 3137, 2933, 1602, 1539, 1465, 1438, 774, 718, 555. ¹H NMR (400 MHz, DMSO–d₆, 304 K): δ = 1.74–1.70 (m, 4H), 2.36–2.33 (m, 2H), 2.57–2.54 (m, 2H), 5.76 (s, 1H), 7.64 (t, 2H, J = 7.6), 7.78–7.75 (m, 1H), 8.06 (d, 2H, J = 7.9). Anal. Calcd for C₁₅H₁₄N₂S: C, 70.83; H, 5.55. Found: C, 70.91; H, 5.62.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Synthesis of 2-phenyl-5,6,7,8-tetrahydroimidazo[2,1–b][1,3]benzothiazole.
	Fig. 2. Molecular structure of I (two crystallographically independent molecules are presented). Displacement ellipsoids are shown at the 50% probability level. H atoms are depicted as small spheres of arbitrary radius.

2-Phenyl-5,6,7,8-tetrahydroimidazo[2,1-b][1,3]benzothiazole top

Crystal data top

C₁₅H₁₄N₂S	F(000) = 1072
M_r = 254.34	D_x = 1.363 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 440–442 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.523 (3) Å	Cell parameters from 769 reflections
b = 10.699 (3) Å	θ = 2.2–19.4°
c = 18.930 (5) Å	µ = 0.24 mm⁻¹
β = 102.291 (6)°	T = 120 K
V = 2478.2 (11) Å³	Needle, colourless
Z = 8	0.30 × 0.05 × 0.03 mm

Data collection top

Bruker APEXII CCD diffractometer	7558 independent reflections
Radiation source: fine-focus sealed tube	3223 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 30.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −17→17
T_min = 0.931, T_max = 0.993	k = −15→15
33479 measured reflections	l = −27→27

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0349P)²] where P = (F_o² + 2F_c²)/3
7558 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₅H₁₄N₂S	V = 2478.2 (11) Å³
M_r = 254.34	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.523 (3) Å	µ = 0.24 mm⁻¹
b = 10.699 (3) Å	T = 120 K
c = 18.930 (5) Å	0.30 × 0.05 × 0.03 mm
β = 102.291 (6)°

Data collection top

Bruker APEXII CCD diffractometer	7558 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	3223 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.993	R_int = 0.068
33479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 0.93	Δρ_max = 0.36 e Å⁻³
7558 reflections	Δρ_min = −0.45 e Å⁻³
325 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N1	0.3882 (2)	0.6184 (2)	0.11553 (14)	0.0237 (6)
C2	0.3823 (3)	0.5036 (3)	0.14946 (16)	0.0212 (7)
C3	0.4704 (3)	0.4301 (3)	0.14592 (16)	0.0219 (7)
H3	0.4850	0.3481	0.1647	0.026*
N4	0.5337 (2)	0.5003 (2)	0.10923 (14)	0.0205 (6)
C4A	0.6340 (3)	0.4902 (3)	0.08809 (16)	0.0209 (7)
C5	0.7062 (2)	0.3795 (3)	0.10652 (18)	0.0248 (7)
H5A	0.6796	0.3105	0.0725	0.030*
H5B	0.7049	0.3508	0.1560	0.030*
C6	0.8230 (3)	0.4141 (3)	0.10196 (18)	0.0277 (8)
H6A	0.8567	0.4646	0.1447	0.033*
H6B	0.8668	0.3370	0.1024	0.033*
C7	0.8246 (3)	0.4884 (3)	0.03323 (17)	0.0254 (7)
H7A	0.7920	0.4368	−0.0093	0.030*
H7B	0.9014	0.5058	0.0309	0.030*
C8	0.7619 (3)	0.6131 (3)	0.02925 (17)	0.0255 (7)
H8A	0.8072	0.6760	0.0605	0.031*
H8B	0.7463	0.6448	−0.0210	0.031*
C8A	0.6568 (2)	0.5938 (3)	0.05377 (16)	0.0212 (7)
S9	0.55424 (7)	0.70942 (8)	0.04714 (5)	0.0253 (2)
C9A	0.4804 (3)	0.6118 (3)	0.09283 (16)	0.0213 (7)
C10	0.2878 (3)	0.4714 (3)	0.18064 (17)	0.0229 (7)
C11	0.2908 (3)	0.3708 (3)	0.22804 (17)	0.0250 (7)
H11	0.3563	0.3241	0.2426	0.030*
C12	0.1987 (3)	0.3383 (3)	0.25409 (17)	0.0292 (8)
H12	0.2018	0.2695	0.2862	0.035*
C13	0.1024 (3)	0.4053 (3)	0.23360 (18)	0.0297 (8)
H13	0.0393	0.3822	0.2509	0.036*
C14	0.0992 (3)	0.5066 (3)	0.18754 (18)	0.0297 (8)
H14	0.0339	0.5539	0.1737	0.036*
C15	0.1911 (3)	0.5393 (3)	0.16149 (17)	0.0267 (8)
H15	0.1879	0.6091	0.1301	0.032*
N16	−0.1213 (2)	0.9124 (2)	0.11849 (14)	0.0252 (6)
C17	−0.1096 (3)	1.0225 (3)	0.15894 (17)	0.0224 (7)
C18	−0.0110 (3)	1.0785 (3)	0.15889 (16)	0.0230 (7)
H18	0.0156	1.1548	0.1818	0.028*
N19	0.0414 (2)	1.0016 (2)	0.11889 (14)	0.0218 (6)
C19A	0.1393 (3)	0.9974 (3)	0.09439 (17)	0.0230 (7)
C20	0.2241 (3)	1.0980 (3)	0.11148 (17)	0.0260 (8)
H20A	0.2640	1.0906	0.1624	0.031*
H20B	0.1887	1.1811	0.1049	0.031*
C21	0.3034 (3)	1.0841 (3)	0.06097 (18)	0.0278 (8)
H21A	0.3690	1.1358	0.0793	0.033*
H21B	0.2683	1.1156	0.0124	0.033*
C22	0.3384 (3)	0.9486 (3)	0.05454 (18)	0.0282 (8)
H22A	0.3731	0.9166	0.1031	0.034*
H22B	0.3934	0.9450	0.0239	0.034*
C23	0.2406 (3)	0.8651 (3)	0.02141 (17)	0.0252 (8)
H23A	0.2206	0.8784	−0.0315	0.030*
H23B	0.2608	0.7761	0.0304	0.030*
C23A	0.1451 (3)	0.8957 (3)	0.05424 (17)	0.0252 (7)
S24	0.02778 (7)	0.79992 (8)	0.04362 (5)	0.0269 (2)
C24A	−0.0288 (3)	0.9037 (3)	0.09640 (16)	0.0218 (7)
C25	−0.1985 (3)	1.0704 (3)	0.19086 (17)	0.0247 (7)
C26	−0.1767 (3)	1.1565 (3)	0.24797 (17)	0.0266 (8)
H26	−0.1036	1.1819	0.2669	0.032*
C27	−0.2608 (3)	1.2052 (3)	0.27725 (17)	0.0284 (8)
H27	−0.2448	1.2638	0.3158	0.034*
C28	−0.3676 (3)	1.1686 (3)	0.25042 (18)	0.0309 (8)
H28	−0.4250	1.2023	0.2704	0.037*
C29	−0.3911 (3)	1.0825 (3)	0.19427 (19)	0.0320 (8)
H29	−0.4645	1.0571	0.1760	0.038*
C30	−0.3071 (3)	1.0334 (3)	0.16478 (18)	0.0288 (8)
H30	−0.3236	0.9742	0.1266	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0236 (16)	0.0247 (16)	0.0223 (15)	0.0008 (12)	0.0038 (12)	0.0008 (11)
C2	0.0226 (18)	0.0226 (18)	0.0176 (16)	−0.0013 (13)	0.0027 (13)	−0.0033 (13)
C3	0.0264 (19)	0.0189 (17)	0.0217 (17)	0.0003 (13)	0.0082 (14)	0.0012 (13)
N4	0.0203 (15)	0.0194 (14)	0.0222 (15)	0.0007 (11)	0.0056 (11)	−0.0013 (11)
C4A	0.0207 (18)	0.0205 (17)	0.0207 (17)	0.0004 (13)	0.0025 (13)	−0.0032 (13)
C5	0.0242 (19)	0.0234 (18)	0.0280 (19)	0.0038 (14)	0.0087 (14)	0.0019 (14)
C6	0.0255 (19)	0.0277 (19)	0.0293 (19)	0.0043 (15)	0.0041 (15)	0.0022 (15)
C7	0.0232 (18)	0.0280 (19)	0.0267 (19)	−0.0010 (14)	0.0093 (14)	−0.0037 (14)
C8	0.0258 (19)	0.0275 (19)	0.0237 (18)	−0.0024 (14)	0.0065 (14)	0.0008 (14)
C8A	0.0233 (18)	0.0203 (17)	0.0194 (17)	−0.0003 (13)	0.0031 (13)	−0.0019 (13)
S9	0.0254 (5)	0.0210 (4)	0.0300 (5)	0.0024 (4)	0.0073 (4)	0.0033 (4)
C9A	0.0233 (18)	0.0189 (17)	0.0208 (17)	0.0013 (13)	0.0025 (13)	−0.0038 (13)
C10	0.0221 (18)	0.0250 (18)	0.0218 (17)	−0.0025 (13)	0.0053 (14)	−0.0044 (13)
C11	0.0261 (19)	0.0234 (18)	0.0262 (19)	0.0019 (14)	0.0071 (14)	−0.0031 (14)
C12	0.038 (2)	0.0266 (19)	0.0237 (19)	−0.0050 (15)	0.0087 (16)	−0.0005 (14)
C13	0.027 (2)	0.033 (2)	0.031 (2)	−0.0085 (16)	0.0101 (15)	−0.0087 (16)
C14	0.0192 (18)	0.040 (2)	0.029 (2)	0.0017 (15)	0.0030 (15)	−0.0046 (16)
C15	0.0261 (19)	0.033 (2)	0.0224 (18)	−0.0005 (15)	0.0074 (14)	−0.0006 (14)
N16	0.0287 (17)	0.0234 (15)	0.0229 (15)	−0.0014 (12)	0.0040 (12)	0.0014 (12)
C17	0.0249 (19)	0.0205 (17)	0.0209 (17)	0.0003 (13)	0.0032 (14)	0.0006 (13)
C18	0.0278 (19)	0.0188 (17)	0.0220 (18)	0.0022 (14)	0.0038 (14)	−0.0012 (13)
N19	0.0238 (15)	0.0209 (14)	0.0201 (15)	−0.0018 (11)	0.0035 (11)	−0.0012 (11)
C19A	0.0231 (18)	0.0224 (18)	0.0224 (18)	0.0016 (14)	0.0026 (14)	0.0025 (13)
C20	0.0263 (19)	0.0229 (18)	0.0274 (19)	−0.0010 (14)	0.0024 (14)	−0.0018 (14)
C21	0.027 (2)	0.0255 (19)	0.030 (2)	−0.0035 (15)	0.0035 (15)	−0.0016 (15)
C22	0.030 (2)	0.029 (2)	0.0267 (19)	0.0067 (15)	0.0085 (15)	0.0044 (14)
C23	0.031 (2)	0.0228 (18)	0.0215 (18)	0.0062 (14)	0.0054 (15)	0.0026 (13)
C23A	0.029 (2)	0.0241 (19)	0.0217 (18)	0.0014 (14)	0.0037 (14)	0.0059 (14)
S24	0.0317 (5)	0.0198 (4)	0.0286 (5)	−0.0002 (4)	0.0051 (4)	−0.0023 (4)
C24A	0.0260 (19)	0.0176 (17)	0.0213 (17)	−0.0016 (13)	0.0037 (14)	0.0000 (13)
C25	0.028 (2)	0.0225 (18)	0.0238 (18)	0.0006 (14)	0.0050 (14)	0.0070 (14)
C26	0.027 (2)	0.030 (2)	0.0217 (18)	−0.0011 (14)	0.0031 (14)	0.0086 (14)
C27	0.036 (2)	0.0271 (19)	0.0227 (18)	0.0041 (16)	0.0075 (15)	0.0067 (15)
C28	0.033 (2)	0.031 (2)	0.032 (2)	0.0081 (16)	0.0136 (16)	0.0109 (15)
C29	0.024 (2)	0.032 (2)	0.039 (2)	−0.0034 (15)	0.0054 (16)	0.0086 (17)
C30	0.029 (2)	0.030 (2)	0.0269 (19)	−0.0025 (15)	0.0032 (15)	0.0002 (14)

Geometric parameters (Å, º) top

N1—C9A	1.317 (4)	N16—C24A	1.316 (4)
N1—C2	1.395 (4)	N16—C17	1.395 (4)
C2—C3	1.368 (4)	C17—C18	1.373 (4)
C2—C10	1.472 (4)	C17—C25	1.468 (4)
C3—N4	1.382 (4)	C18—N19	1.376 (4)
C3—H3	0.9500	C18—H18	0.9500
N4—C9A	1.370 (4)	N19—C24A	1.376 (4)
N4—C4A	1.400 (4)	N19—C19A	1.400 (4)
C4A—C8A	1.346 (4)	C19A—C23A	1.338 (4)
C4A—C5	1.486 (4)	C19A—C20	1.498 (4)
C5—C6	1.529 (4)	C20—C21	1.526 (4)
C5—H5A	0.9900	C20—H20A	0.9900
C5—H5B	0.9900	C20—H20B	0.9900
C6—C7	1.528 (4)	C21—C22	1.527 (4)
C6—H6A	0.9900	C21—H21A	0.9900
C6—H6B	0.9900	C21—H21B	0.9900
C7—C8	1.542 (4)	C22—C23	1.538 (4)
C7—H7A	0.9900	C22—H22A	0.9900
C7—H7B	0.9900	C22—H22B	0.9900
C8—C8A	1.500 (4)	C23—C23A	1.497 (4)
C8—H8A	0.9900	C23—H23A	0.9900
C8—H8B	0.9900	C23—H23B	0.9900
C8A—S9	1.769 (3)	C23A—S24	1.767 (3)
S9—C9A	1.742 (3)	S24—C24A	1.742 (3)
C10—C15	1.392 (4)	C25—C30	1.401 (4)
C10—C11	1.397 (4)	C25—C26	1.402 (4)
C11—C12	1.392 (4)	C26—C27	1.392 (4)
C11—H11	0.9500	C26—H26	0.9500
C12—C13	1.385 (5)	C27—C28	1.382 (5)
C12—H12	0.9500	C27—H27	0.9500
C13—C14	1.386 (5)	C28—C29	1.390 (5)
C13—H13	0.9500	C28—H28	0.9500
C14—C15	1.390 (4)	C29—C30	1.395 (5)
C14—H14	0.9500	C29—H29	0.9500
C15—H15	0.9500	C30—H30	0.9500

C9A—N1—C2	103.8 (3)	C24A—N16—C17	103.7 (3)
C3—C2—N1	111.2 (3)	C18—C17—N16	111.0 (3)
C3—C2—C10	127.7 (3)	C18—C17—C25	127.6 (3)
N1—C2—C10	121.1 (3)	N16—C17—C25	121.3 (3)
C2—C3—N4	105.5 (3)	C17—C18—N19	105.9 (3)
C2—C3—H3	127.2	C17—C18—H18	127.1
N4—C3—H3	127.2	N19—C18—H18	127.1
C9A—N4—C3	106.4 (3)	C18—N19—C24A	106.1 (3)
C9A—N4—C4A	115.2 (3)	C18—N19—C19A	139.1 (3)
C3—N4—C4A	138.3 (3)	C24A—N19—C19A	114.8 (3)
C8A—C4A—N4	111.7 (3)	C23A—C19A—N19	111.8 (3)
C8A—C4A—C5	126.0 (3)	C23A—C19A—C20	125.8 (3)
N4—C4A—C5	122.2 (3)	N19—C19A—C20	122.4 (3)
C4A—C5—C6	109.6 (3)	C19A—C20—C21	108.7 (3)
C4A—C5—H5A	109.7	C19A—C20—H20A	109.9
C6—C5—H5A	109.7	C21—C20—H20A	109.9
C4A—C5—H5B	109.7	C19A—C20—H20B	109.9
C6—C5—H5B	109.7	C21—C20—H20B	109.9
H5A—C5—H5B	108.2	H20A—C20—H20B	108.3
C7—C6—C5	111.1 (3)	C20—C21—C22	112.2 (3)
C7—C6—H6A	109.4	C20—C21—H21A	109.2
C5—C6—H6A	109.4	C22—C21—H21A	109.2
C7—C6—H6B	109.4	C20—C21—H21B	109.2
C5—C6—H6B	109.4	C22—C21—H21B	109.2
H6A—C6—H6B	108.0	H21A—C21—H21B	107.9
C6—C7—C8	113.1 (3)	C21—C22—C23	111.5 (3)
C6—C7—H7A	109.0	C21—C22—H22A	109.3
C8—C7—H7A	109.0	C23—C22—H22A	109.3
C6—C7—H7B	109.0	C21—C22—H22B	109.3
C8—C7—H7B	109.0	C23—C22—H22B	109.3
H7A—C7—H7B	107.8	H22A—C22—H22B	108.0
C8A—C8—C7	109.7 (3)	C23A—C23—C22	109.9 (3)
C8A—C8—H8A	109.7	C23A—C23—H23A	109.7
C7—C8—H8A	109.7	C22—C23—H23A	109.7
C8A—C8—H8B	109.7	C23A—C23—H23B	109.7
C7—C8—H8B	109.7	C22—C23—H23B	109.7
H8A—C8—H8B	108.2	H23A—C23—H23B	108.2
C4A—C8A—C8	123.6 (3)	C19A—C23A—C23	124.0 (3)
C4A—C8A—S9	112.6 (2)	C19A—C23A—S24	113.1 (3)
C8—C8A—S9	123.6 (2)	C23—C23A—S24	123.0 (2)
C9A—S9—C8A	89.97 (15)	C24A—S24—C23A	89.70 (15)
N1—C9A—N4	113.1 (3)	N16—C24A—N19	113.3 (3)
N1—C9A—S9	136.4 (3)	N16—C24A—S24	136.1 (3)
N4—C9A—S9	110.5 (2)	N19—C24A—S24	110.6 (2)
C15—C10—C11	118.2 (3)	C30—C25—C26	118.2 (3)
C15—C10—C2	120.2 (3)	C30—C25—C17	121.4 (3)
C11—C10—C2	121.6 (3)	C26—C25—C17	120.4 (3)
C12—C11—C10	120.6 (3)	C27—C26—C25	120.9 (3)
C12—C11—H11	119.7	C27—C26—H26	119.6
C10—C11—H11	119.7	C25—C26—H26	119.6
C13—C12—C11	120.6 (3)	C28—C27—C26	120.2 (3)
C13—C12—H12	119.7	C28—C27—H27	119.9
C11—C12—H12	119.7	C26—C27—H27	119.9
C12—C13—C14	119.2 (3)	C27—C28—C29	120.0 (3)
C12—C13—H13	120.4	C27—C28—H28	120.0
C14—C13—H13	120.4	C29—C28—H28	120.0
C13—C14—C15	120.4 (3)	C28—C29—C30	120.1 (3)
C13—C14—H14	119.8	C28—C29—H29	120.0
C15—C14—H14	119.8	C30—C29—H29	120.0
C14—C15—C10	121.1 (3)	C29—C30—C25	120.7 (3)
C14—C15—H15	119.5	C29—C30—H30	119.6
C10—C15—H15	119.5	C25—C30—H30	119.6

C9A—N1—C2—C3	−0.5 (3)	C24A—N16—C17—C18	1.2 (4)
C9A—N1—C2—C10	−177.9 (3)	C24A—N16—C17—C25	177.0 (3)
N1—C2—C3—N4	0.3 (4)	N16—C17—C18—N19	−1.1 (4)
C10—C2—C3—N4	177.5 (3)	C25—C17—C18—N19	−176.5 (3)
C2—C3—N4—C9A	0.0 (3)	C17—C18—N19—C24A	0.5 (3)
C2—C3—N4—C4A	177.0 (3)	C17—C18—N19—C19A	178.2 (3)
C9A—N4—C4A—C8A	−1.3 (4)	C18—N19—C19A—C23A	−178.6 (3)
C3—N4—C4A—C8A	−178.1 (3)	C24A—N19—C19A—C23A	−1.0 (4)
C9A—N4—C4A—C5	175.3 (3)	C18—N19—C19A—C20	0.5 (6)
C3—N4—C4A—C5	−1.5 (6)	C24A—N19—C19A—C20	178.1 (3)
C8A—C4A—C5—C6	17.0 (4)	C23A—C19A—C20—C21	14.3 (4)
N4—C4A—C5—C6	−159.1 (3)	N19—C19A—C20—C21	−164.7 (3)
C4A—C5—C6—C7	−45.4 (4)	C19A—C20—C21—C22	−45.1 (4)
C5—C6—C7—C8	61.3 (4)	C20—C21—C22—C23	62.7 (4)
C6—C7—C8—C8A	−42.5 (4)	C21—C22—C23—C23A	−43.5 (4)
N4—C4A—C8A—C8	175.9 (3)	N19—C19A—C23A—C23	−179.2 (3)
C5—C4A—C8A—C8	−0.6 (5)	C20—C19A—C23A—C23	1.7 (5)
N4—C4A—C8A—S9	0.6 (3)	N19—C19A—C23A—S24	0.8 (4)
C5—C4A—C8A—S9	−175.9 (3)	C20—C19A—C23A—S24	−178.3 (2)
C7—C8—C8A—C4A	12.9 (4)	C22—C23—C23A—C19A	13.0 (4)
C7—C8—C8A—S9	−172.2 (2)	C22—C23—C23A—S24	−167.0 (2)
C4A—C8A—S9—C9A	0.2 (3)	C19A—C23A—S24—C24A	−0.3 (3)
C8—C8A—S9—C9A	−175.1 (3)	C23—C23A—S24—C24A	179.7 (3)
C2—N1—C9A—N4	0.6 (3)	C17—N16—C24A—N19	−0.9 (3)
C2—N1—C9A—S9	−178.9 (3)	C17—N16—C24A—S24	−179.3 (3)
C3—N4—C9A—N1	−0.4 (4)	C18—N19—C24A—N16	0.3 (4)
C4A—N4—C9A—N1	−178.2 (3)	C19A—N19—C24A—N16	−178.0 (3)
C3—N4—C9A—S9	179.2 (2)	C18—N19—C24A—S24	179.1 (2)
C4A—N4—C9A—S9	1.5 (3)	C19A—N19—C24A—S24	0.8 (3)
C8A—S9—C9A—N1	178.6 (4)	C23A—S24—C24A—N16	178.2 (4)
C8A—S9—C9A—N4	−0.9 (2)	C23A—S24—C24A—N19	−0.3 (2)
C3—C2—C10—C15	−160.7 (3)	C18—C17—C25—C30	154.6 (3)
N1—C2—C10—C15	16.3 (5)	N16—C17—C25—C30	−20.4 (5)
C3—C2—C10—C11	17.3 (5)	C18—C17—C25—C26	−24.4 (5)
N1—C2—C10—C11	−165.7 (3)	N16—C17—C25—C26	160.6 (3)
C15—C10—C11—C12	1.2 (5)	C30—C25—C26—C27	−0.9 (5)
C2—C10—C11—C12	−176.8 (3)	C17—C25—C26—C27	178.1 (3)
C10—C11—C12—C13	−0.1 (5)	C25—C26—C27—C28	0.3 (5)
C11—C12—C13—C14	−0.9 (5)	C26—C27—C28—C29	0.3 (5)
C12—C13—C14—C15	0.9 (5)	C27—C28—C29—C30	−0.3 (5)
C13—C14—C15—C10	0.2 (5)	C28—C29—C30—C25	−0.3 (5)
C11—C10—C15—C14	−1.2 (5)	C26—C25—C30—C29	0.9 (5)
C2—C10—C15—C14	176.8 (3)	C17—C25—C30—C29	−178.1 (3)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂S
M_r	254.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	12.523 (3), 10.699 (3), 18.930 (5)
β (°)	102.291 (6)
V (Å³)	2478.2 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.05 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.931, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	33479, 7558, 3223
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.157, 0.93
No. of reflections	7558
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.45

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful to the Ministry of Education and Science of the Russian Federation (State contract No. 426).

References

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