10-Benzyl-10H-phenothia­zine 9-oxide

Zhouqing Xu; Yanchun Sun; Lei Yang; Qiang Wang

doi:10.1107/S160053680902577X

. 2009 Jul 8;65(Pt 8):o1799. doi: 10.1107/S160053680902577X

10-Benzyl-10H-phenothiazine 9-oxide

Zhouqing Xu ^a, Yanchun Sun ^b, Lei Yang ^a, Qiang Wang ^a,^*

PMCID: PMC2977256 PMID: 21583505

Abstract

In the title compound, C₁₉H₁₅NOS, the butterfly angle between the mean planes defined by the S, N and phenyl C atoms of the two wings of the phenothiazine unit is 23.4 (1)°. In the crystal, a supramolecular two-dimensional arrangement arises from weak intermolecular C—H⋯O interactions.

Related literature

For applications of phenothiazines, see: Miller et al. (1999 ▶); Wermuth (2003 ▶); Wang et al. (2008 ▶); Lam et al. (2001 ▶). For the synthesis, see: Zhu et al. (2006 ▶); Gilman et al. (1954 ▶).

Experimental

Crystal data

C₁₉H₁₅NOS
M _r = 305.38
Monoclinic,
a = 6.2819 (4) Å
b = 11.9259 (8) Å
c = 20.3220 (14) Å
β = 94.6140 (10)°
V = 1517.54 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.30 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.939, T _max = 0.961
7251 measured reflections
2511 independent reflections
1872 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.094
S = 1.02
2511 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902577X/pv2174sup1.cif

e-65-o1799-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902577X/pv2174Isup2.hkl

e-65-o1799-Isup2.hkl^{(123.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O1ⁱ	0.97	2.52	3.431 (2)	157
C18—H18⋯O1ⁱⁱ	0.93	2.57	3.442 (3)	157

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the Foundation of Henan Polytechnic University for Doctor Teachers, and the authors thank Ms Q. F. Wang for her support with the single-crystal X-ray diffraction data collection.

supplementary crystallographic information

Comment

Phenothiazine molecule is a well known heterocycle. The phenothiazine structure occurs in many synthetic dyes, electroluminescent materials (Miller et al., 1999) and drugs, especially various antipsychotic drugs, e.g., chlorpromazine and promethazine (Wermuth, 2003). Recently, some new applications of phenothazine derivatives have been found in medicines, such as antitubercular (Wang et al., 2008) and antitumor (Lam et al., 2001). As a part of our programme devoted to the new applications of phenothazine derivatives in medicne, we report herein the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1, with its respective labels. The butterfly angle between the mean-planes defined by atoms S1/N1/C1-C6 and S1/N1/C7-C12 is 23.4 (1) °. The crystal packing (Fig. 2) consists of two-dimensional infinite plane along the a axis generated by intermolecular interactions of the weak C—H···O hydrogen bonds (details are in Table 1).

Experimental

All reagents were of analytical grade. The title compound was prepared according to a literature method (Zhu et al., 2006; Gilman et al., 1954) from N-benzylphenothiazine. The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared spectra and elemental analyses. Single crystals of the title compound were obtained by slow evaporation of its ethanol solution. The X-ray diffraction studies were made at room temperature.