10-(Prop-2-yn-1-yl)-2,7-diaza­phenothia­zine

Morak-Młodawska, B.; Suwińska, K.; Pluta, K.; Jeleń, M.

doi:10.1107/S1600536812018879

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1590-o1591

doi:10.1107/S1600536812018879

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10-(Prop-2-yn-1-yl)-2,7-diazaphenothiazine †

Beata Morak-Młodawska,^a Kinga Suwińska,^b,^c Krystian Pluta ^a ^* and Małgorzata Jeleń ^a

^aDepartment of Organic Chemistry, The Medical University of Silesia, ul. Jagiellońska 4, 41-200 Sosnowiec, Poland, ^bInstitute of Physical Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland, and ^cFaculty of Biology and Environmental Sciences, Cardinal Stefan Wyszynski University, ul. Wóycickiego 1/3, 01 938 Warszawa, Poland
^*Correspondence e-mail: pluta@sum.edu.pl

(Received 3 April 2012; accepted 26 April 2012; online 2 May 2012)

In the title molecule [systematic name: 10-(prop-2-yn-1-yl)dipyrido[3,4-b:3′,4′-e][1,4]thiazine], C₁₃H₉N₃S, the dihedral angle between the two pyridine rings is 146.33 (7)° and the angle between two halves of the thiazine ring is 138.84 (8)°, resulting in a butterfly shape for the tricyclic system. The central thiazine ring adopts a boat conformation, with the 2-propynyl substituent at the thiazine N atom located in a pseudo-equatorial position and oriented to the concave side of the diazaphenothiazine system. In the crystal, molecules are arranged via π–π interactions between the pyridine rings [centroid–centroid distances = 3.838 (1) and 3.845 (1) Å] into stacks extending along [001]. There are C—H⋯C and C—H⋯N interactions between molecules of neighbouring stacks.

Related literature

For recent literature on the biological activity of phenothiazines, see: Aaron et al. (2009 ); Pluta et al. (2011 ). For the structure of 10-(2-propynyl)phenothiazine and its transformations into anticancer derivatives, see: Bisi et al. (2008 ). For the synthesis and the anticancer and immunosuppressive activity of 2,7-diazaphenothiazines, see: Morak-Młodawska & Pluta (2009 ); Zimecki et al. (2009 ); Pluta et al. (2010 ). For planar and folded structures of the 2,7-diazaphenothiazine system, see: Morak et al. (2002 ); Morak-Młodawska et al. (2010 ). For alkylation of azaphenothiazines, see: Pluta et al. (2009 ).

Experimental

Crystal data

C₁₃H₉N₃S
M_r = 239.29
Monoclinic, P 2₁ /c
a = 14.1150 (9) Å
b = 10.1909 (6) Å
c = 7.6749 (5) Å
β = 104.212 (3)°
V = 1070.20 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 100 K
0.60 × 0.50 × 0.35 mm

Data collection

Nonius KappaCCD diffractometer upgraded with APEXII detector
7015 measured reflections
2407 independent reflections
2011 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.114
S = 1.11
2407 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N2ⁱ	0.95	2.62	3.457 (3)	147
C13—H13⋯C11ⁱⁱ	0.95	2.78	3.677 (3)	159
C13—H13⋯C12ⁱⁱ	0.95	2.78	3.686 (3)	161
C3—H3⋯C13ⁱ	0.95	2.78	3.662 (3)	155
C8—H8⋯C13ⁱⁱⁱ	0.95	2.69	3.407 (3)	133
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812018879/gk2475sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018879/gk2475Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018879/gk2475Isup3.cml

checkCIF report

Comment top

Phenothiazines exhibit not only recognized neuroleptic, antihistaminic and antitussive activities but recently also anticancer, antibacterial and reversal multidrug resistance [Aaron et al., (2009); Pluta et al., (2011)]. The modifications of the phenothiazine structures are mainly directed into the introduction of new pharmacophoric substituents at the thiazine nitrogen atom and the substitution of the benzene ring with an azine ring (Pluta et al., 2009, 2011). Synthesis of substituted 10-(2-propynyl)phenothiazines and their transformations into various aminobutynyl derivatives of anticancer and multidrug resistance reverting activities was reported by Bisi et al. (2008). We modified the phenothiazine structure via the substitution of the benzene ring with the pyridine ring to form 2,7-diazaphenothiazines (Morak-Młodawska & Pluta, 2009) possessing anticancer and immunosuppressive activities (Zimecki et al., 2009; Pluta et al. 2010). Alkylation of azaphenothiazines proceeds at the thiazine and/or the azine nitrogen atoms, depending on the reaction conditions (Pluta et al., 2009). N-Alkylation of 10H-2,7-diazaphenothiazine led to both types of the products showing planar and folded 2,7-diazaphenothiazine ring system (Morak-Młodawska et al., 2010). 10H-2,7-Diazaphenothiazine was transformed into the title compound, C₁₃H₉N₃S, a convenient substrate to other 2,7-diazaphenothiazine derivatives using aminomethylation or 1,3-dipolar cycloaddition. The X-ray study showed the propynyl group to be attached to the thiazine nitrogen atom. In the molecule, the butterfly angle between the two pyridine rings is 146.33 (7)° and the angle between two halves of the thiazine ring is 138.84 (8)°. The 2-propynyl substituent is in a pseudo-equatorial position with the angle S5···N10–C11 of 163.8 (2)° and directed to the concave side of the diazaphenothiazine system with the angle between the N10/C11/C12/C13 and C4a/C5a/C9a/C10a planes of 86.3 (1)°. The thiazine nitrogen atom shows pyramidality as the sum of the C–N10–C bond angles is 356.1 (1)°. Hydrogen bond C4–H4···N2 (Table 1) results in one-dimensional polymeric chain parallel to the b axis. Acidic hydrogen atom H13 is in close contact to C11 and C12 atoms of the propynyl substituent (both H···C distances equal to 2.78 Å). This suggests, that H13 is involved in C–H···C interactions to these two carbon atoms rather than in the C–H···π interaction to the π system of the triple C12≡C13 bond (H13···center_C12_≡_C13 distance of 2.96 Å ). Additionally, the C12≡ C13 bond π electrons interact with two aromatic H atoms (H3 and H8) of two other adjacent molecules with short C–H···C intermolecular contacts (less than the sum of van der Waals radii) between H3 and H8, and C13 (see Table 1). On the basis of these interactions a three-dimensional network is formed. Molecules π-stack along the c axis. Aromatic rings N2/C1/C10a/C4a/C4/C3 π-stack with centroid-to-centroid distance of 3.845 (1) Å, similarly, for rings N7/C6/C5A/C9A/C9/C8 the centroid-to-centroid distance is 3.838 (1) Å (see Figure 2).

Related literature top

For recent literature on the biological activity of phenothiazines, see: Aaron et al. (2009); Pluta et al. (2011). For the structure of 10-(2-propynyl)phenothiazine and its transformations into anticancer derivatives, see: Bisi et al. (2008). For the synthesis and the anticancer and immunosuppressive activity of 2,7-diazaphenothiazines, see: Morak-Młodawska & Pluta (2009); Zimecki et al. (2009); Pluta et al. (2010). For planar and folded structures of the 2,7-diazaphenothiazine system, see: Morak et al. (2002); Morak-Młodawska et al. (2010). For alkylation of azaphenothiazines, see: Pluta et al. (2009).

Experimental top

To a suspension of 10H-2,7-diazaphenothiazine (100 mg, 0.5 mmol) in 5 ml DMF potassium tert-butoxide (80 mg, 0.72 mmol) was added. The mixture was stirred at room temperature for 1 h. Then a solution of propargyl bromide (80 mg, 0.64 mmol) in toluene was added dropwise. The solution was stirred at room temperature for 24 h and poured into water (15 ml), extracted with methylene chloride (15 ml), dried with Na₂SO₄ and evaporated to the brown oil. The residue was purified by column chromatography (silica gel, CHCl₃) to yield 10-(2-propynyl)-2,7-diazaphenothiazine (72 mg, 60%), mp. 149–150°C. ¹H NMR in CDCl₃: δ 2.57 (t, J = 2.5 Hz, 1H), 4.54(d, J = 2.5 Hz, 2H), 7.14 (m, 2H, H-9, H-4), 8.12 (s, 1H, H-1), 8.22 (d, J = 5.5 Hz, H-3), 8.35 (d, J = 5.5 Hz, H-8), 8.40 (s, 1H, H-6). FAB MS: 240 (M+H, 100), 201 (M—CH₂CCH+1, 45).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP drawing with displacement ellipsoids shown at the 50% probability level.
	Fig. 2. Crystal packing shown along the c axis.

10-(Prop-2-yn-1-yl)-2,7-diazaphenothiazine top

Crystal data top

C₁₃H₉N₃S	F(000) = 496
M_r = 239.29	D_x = 1.485 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2229 reflections
a = 14.1150 (9) Å	θ = 2.5–27.5°
b = 10.1909 (6) Å	µ = 0.28 mm⁻¹
c = 7.6749 (5) Å	T = 100 K
β = 104.212 (3)°	Block, yellow
V = 1070.20 (12) Å³	0.60 × 0.50 × 0.35 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer upgraded with APEXII detector	2011 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 27.5°, θ_min = 3.4°
Detector resolution: 8.3 pixels mm^-1	h = −18→18
ω scan	k = −12→13
7015 measured reflections	l = −9→9
2407 independent 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0285P)² + 1.4885P] where P = (F_o² + 2F_c²)/3
2407 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₃H₉N₃S	V = 1070.20 (12) Å³
M_r = 239.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.1150 (9) Å	µ = 0.28 mm⁻¹
b = 10.1909 (6) Å	T = 100 K
c = 7.6749 (5) Å	0.60 × 0.50 × 0.35 mm
β = 104.212 (3)°

Data collection top

Nonius KappaCCD diffractometer upgraded with APEXII detector	2011 reflections with I > 2σ(I)
7015 measured reflections	R_int = 0.041
2407 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.11	Δρ_max = 0.45 e Å⁻³
2407 reflections	Δρ_min = −0.35 e Å⁻³
154 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
C1	0.92188 (15)	0.1074 (2)	0.5605 (3)	0.0172 (4)
H1	0.9145	0.0148	0.5522	0.021*
C3	1.01573 (17)	0.2865 (2)	0.6685 (3)	0.0218 (5)
H3	1.0762	0.3225	0.7335	0.026*
C4	0.94013 (16)	0.3721 (2)	0.5945 (3)	0.0195 (5)
H4	0.9479	0.4640	0.6135	0.023*
C4a	0.85325 (16)	0.3212 (2)	0.4927 (3)	0.0159 (4)
C5a	0.65940 (16)	0.3263 (2)	0.3914 (3)	0.0164 (4)
C6	0.57174 (16)	0.3834 (2)	0.4013 (3)	0.0197 (5)
H6	0.5703	0.4759	0.4161	0.024*
C8	0.49541 (17)	0.1852 (2)	0.3756 (3)	0.0226 (5)
H8	0.4377	0.1351	0.3665	0.027*
C9	0.58017 (16)	0.1180 (2)	0.3718 (3)	0.0192 (5)
H9	0.5801	0.0249	0.3640	0.023*
C9a	0.66564 (15)	0.1889 (2)	0.3797 (3)	0.0154 (4)
C10a	0.84271 (15)	0.1850 (2)	0.4757 (3)	0.0147 (4)
C11	0.75374 (17)	−0.0072 (2)	0.3179 (3)	0.0182 (5)
H11a	0.8152	−0.0251	0.2819	0.022*
H11b	0.6992	−0.0198	0.2102	0.022*
C12	0.74397 (16)	−0.1054 (2)	0.4530 (3)	0.0194 (5)
C13	0.73370 (18)	−0.1884 (3)	0.5542 (4)	0.0284 (6)
H13	0.7254	−0.2552	0.6356	0.034*
S5	0.75938 (4)	0.42507 (5)	0.37659 (8)	0.01880 (16)
N2	1.00796 (13)	0.15579 (19)	0.6532 (3)	0.0204 (4)
N7	0.48877 (14)	0.3163 (2)	0.3912 (3)	0.0226 (4)
N10	0.75434 (13)	0.12936 (18)	0.3721 (2)	0.0158 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0160 (10)	0.0151 (10)	0.0217 (11)	0.0027 (8)	0.0071 (9)	0.0011 (8)
C3	0.0170 (11)	0.0228 (12)	0.0250 (12)	−0.0042 (10)	0.0041 (9)	−0.0051 (10)
C4	0.0194 (11)	0.0165 (10)	0.0244 (12)	−0.0023 (9)	0.0085 (9)	−0.0050 (9)
C4a	0.0165 (10)	0.0147 (10)	0.0178 (11)	0.0005 (8)	0.0070 (8)	0.0003 (8)
C5a	0.0176 (10)	0.0166 (10)	0.0142 (10)	0.0009 (8)	0.0025 (8)	0.0013 (8)
C6	0.0195 (11)	0.0186 (10)	0.0197 (11)	0.0028 (9)	0.0023 (9)	−0.0007 (9)
C8	0.0168 (11)	0.0245 (12)	0.0250 (12)	−0.0011 (9)	0.0024 (9)	−0.0024 (10)
C9	0.0175 (10)	0.0170 (10)	0.0217 (11)	−0.0004 (9)	0.0022 (9)	−0.0013 (9)
C9a	0.0155 (10)	0.0156 (10)	0.0143 (10)	0.0027 (8)	0.0022 (8)	−0.0005 (8)
C10a	0.0141 (10)	0.0144 (10)	0.0169 (11)	−0.0017 (8)	0.0064 (8)	0.0000 (8)
C11	0.0199 (11)	0.0136 (10)	0.0218 (11)	0.0011 (9)	0.0064 (9)	−0.0028 (9)
C12	0.0149 (10)	0.0177 (10)	0.0250 (12)	0.0000 (9)	0.0037 (9)	−0.0034 (9)
C13	0.0256 (13)	0.0242 (12)	0.0360 (15)	0.0034 (10)	0.0086 (11)	0.0067 (11)
S5	0.0187 (3)	0.0143 (3)	0.0241 (3)	0.0015 (2)	0.0066 (2)	0.0035 (2)
N2	0.0131 (9)	0.0226 (10)	0.0248 (10)	0.0021 (8)	0.0033 (7)	−0.0002 (8)
N7	0.0164 (9)	0.0244 (10)	0.0254 (11)	0.0039 (8)	0.0020 (8)	−0.0014 (8)
N10	0.0119 (8)	0.0185 (9)	0.0167 (9)	0.0014 (7)	0.0030 (7)	−0.0005 (7)

Geometric parameters (Å, º) top

C1—N2	1.342 (3)	C6—H6	0.9500
C1—C10a	1.393 (3)	C8—N7	1.347 (3)
C1—H1	0.9500	C8—C9	1.385 (3)
C3—N2	1.339 (3)	C8—H8	0.9500
C3—C4	1.387 (3)	C9—C9a	1.395 (3)
C3—H3	0.9500	C9—H9	0.9500
C4—C4a	1.383 (3)	C9a—N10	1.405 (3)
C4—H4	0.9500	C10a—N10	1.422 (3)
C4a—C10a	1.398 (3)	C11—N10	1.452 (3)
C4a—S5	1.758 (2)	C11—C12	1.471 (3)
C5a—C6	1.386 (3)	C11—H11a	0.9900
C5a—C9a	1.407 (3)	C11—H11b	0.9900
C5a—S5	1.760 (2)	C12—C13	1.181 (3)
C6—N7	1.342 (3)	C13—H13	0.9500

N2—C1—C10a	123.9 (2)	C8—C9—H9	120.5
N2—C1—H1	118.1	C9a—C9—H9	120.5
C10a—C1—H1	118.1	C9—C9a—N10	122.98 (19)
N2—C3—C4	123.5 (2)	C9—C9a—C5a	116.82 (19)
N2—C3—H3	118.3	N10—C9a—C5a	120.18 (19)
C4—C3—H3	118.3	C1—C10a—C4a	117.7 (2)
C4a—C4—C3	118.8 (2)	C1—C10a—N10	121.87 (19)
C4a—C4—H4	120.6	C4a—C10a—N10	120.42 (19)
C3—C4—H4	120.6	N10—C11—C12	116.42 (19)
C4—C4a—C10a	119.0 (2)	N10—C11—H11a	108.2
C4—C4a—S5	120.91 (17)	C12—C11—H11a	108.2
C10a—C4a—S5	120.04 (17)	N10—C11—H11b	108.2
C6—C5a—C9a	119.5 (2)	C12—C11—H11b	108.2
C6—C5a—S5	120.26 (17)	H11a—C11—H11b	107.3
C9a—C5a—S5	120.09 (16)	C13—C12—C11	176.5 (3)
N7—C6—C5a	124.1 (2)	C12—C13—H13	180.0
N7—C6—H6	117.9	C4a—S5—C5a	98.00 (10)
C5a—C6—H6	117.9	C3—N2—C1	117.1 (2)
N7—C8—C9	124.9 (2)	C6—N7—C8	115.6 (2)
N7—C8—H8	117.6	C9a—N10—C10a	118.21 (18)
C9—C8—H8	117.6	C9a—N10—C11	118.89 (18)
C8—C9—C9a	119.0 (2)	C10a—N10—C11	119.00 (18)

N2—C3—C4—C4a	−2.9 (4)	C4—C4a—S5—C5a	−148.01 (19)
C3—C4—C4a—C10a	3.3 (3)	C10a—C4a—S5—C5a	35.26 (19)
C3—C4—C4a—S5	−173.43 (17)	C6—C5a—S5—C4a	148.16 (19)
C9a—C5a—C6—N7	−3.6 (4)	C9a—C5a—S5—C4a	−36.6 (2)
S5—C5a—C6—N7	171.68 (18)	C4—C3—N2—C1	0.1 (3)
N7—C8—C9—C9a	−1.8 (4)	C10a—C1—N2—C3	2.2 (3)
C8—C9—C9a—N10	−178.4 (2)	C5a—C6—N7—C8	1.9 (3)
C8—C9—C9a—C5a	0.1 (3)	C9—C8—N7—C6	0.8 (4)
C6—C5a—C9a—C9	2.4 (3)	C9—C9a—N10—C10a	−144.8 (2)
S5—C5a—C9a—C9	−172.88 (17)	C5a—C9a—N10—C10a	36.8 (3)
C6—C5a—C9a—N10	−179.1 (2)	C9—C9a—N10—C11	12.8 (3)
S5—C5a—C9a—N10	5.6 (3)	C5a—C9a—N10—C11	−165.6 (2)
N2—C1—C10a—C4a	−1.7 (3)	C1—C10a—N10—C9a	142.9 (2)
N2—C1—C10a—N10	177.10 (19)	C4a—C10a—N10—C9a	−38.3 (3)
C4—C4a—C10a—C1	−1.2 (3)	C1—C10a—N10—C11	−14.6 (3)
S5—C4a—C10a—C1	175.63 (16)	C4a—C10a—N10—C11	164.16 (19)
C4—C4a—C10a—N10	179.98 (19)	C12—C11—N10—C9a	−76.0 (3)
S5—C4a—C10a—N10	−3.2 (3)	C12—C11—N10—C10a	81.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2ⁱ	0.95	2.62	3.457 (3)	147
C13—H13···C11ⁱⁱ	0.95	2.78	3.677 (3)	159
C13—H13···C12ⁱⁱ	0.95	2.78	3.686 (3)	161
C3—H3···C13ⁱ	0.95	2.78	3.662 (3)	155
C8—H8···C13ⁱⁱⁱ	0.95	2.69	3.407 (3)	133

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

Experimental details

Crystal data
Chemical formula	C₁₃H₉N₃S
M_r	239.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.1150 (9), 10.1909 (6), 7.6749 (5)
β (°)	104.212 (3)
V (Å³)	1070.20 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.60 × 0.50 × 0.35

Data collection
Diffractometer	Nonius KappaCCD diffractometer upgraded with APEXII detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7015, 2407, 2011
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.114, 1.11
No. of reflections	2407
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.35

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2ⁱ	0.95	2.62	3.457 (3)	147
C13—H13···C11ⁱⁱ	0.95	2.78	3.677 (3)	159
C13—H13···C12ⁱⁱ	0.95	2.78	3.686 (3)	161
C3—H3···C13ⁱ	0.95	2.78	3.662 (3)	155
C8—H8···C13ⁱⁱⁱ	0.95	2.69	3.407 (3)	133

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

Footnotes

†Azinyl sulfides. Part CXXVII.

Acknowledgements

The work was supported by the Medical University of Silesia (grant KNW-1–073/P/1/0).

References

Aaron, J. J., Gaye Seye, M. D., Trajkovska, S. & Motohashi, N. (2009). Top. Heterocycl. Chem. 16, 153–231. CrossRef CAS Google Scholar
Bisi, A., Meli, M., Gobbi, S., Rampa, A., Tolomeo, M. & Dusonchet, L. (2008). Bioorg. Med. Chem. 16, 6474–6482. Web of Science CrossRef PubMed CAS Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Morak, B., Pluta, K. & Suwińska, K. (2002). Heterocycl. Commun. 8, 331–334. CrossRef CAS Google Scholar
Morak-Młodawska, B. & Pluta, K. (2009). Heterocycles, 78, 1289–1298. Google Scholar
Morak-Młodawska, B., Pluta, K., Suwińska, K. & Jeleń, M. (2010). Heterocycles, 81, 2511–2522. Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Pluta, K., Jeleń, M., Morak-Młodawska, B., Zimecki, M., Artym, J. & Kocięba, M. (2010). Pharmacol. Rep. 62, 319–332. Web of Science CrossRef CAS PubMed Google Scholar
Pluta, K., Morak-Młodawska, B. & Jeleń, M. (2009). J. Heterocycl. Chem. 46, 355–391. Web of Science CrossRef CAS Google Scholar
Pluta, K., Morak-Młodawska, B. & Jeleń, M. (2011). Eur. J. Med. Chem. 46, 3179–3189. 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
Zimecki, M., Artym, J., Kocięba, M., Pluta, K., Morak-Młodawska, B. & Jeleń, M. (2009). Cell. Mol. Biol. Lett. 14, 622–635. Web of Science CrossRef PubMed CAS Google Scholar