10-Benzyl-10H-phenothia-zine 9-oxide.

In the title compound, C(19)H(15)NOS, 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 supra-molecular two-dimensional arrangement arises from weak inter-molecular C-H⋯O inter-actions.

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 = 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

Δρmax = 0.17 e Å−3

Δρmin = −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.

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

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

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

C19H15NOS	F(000) = 640
Mr = 305.38	Dx = 1.337 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1664 reflections
a = 6.2819 (4) Å	θ = 2.6–22.2°
b = 11.9259 (8) Å	µ = 0.21 mm−1
c = 20.3220 (14) Å	T = 296 K
β = 94.614 (1)°	Block, yellow
V = 1517.54 (18) Å3	0.30 × 0.22 × 0.19 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2511 independent reflections
Radiation source: fine-focus sealed tube	1872 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 24.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→6
Tmin = 0.939, Tmax = 0.961	k = −13→13
7251 measured reflections	l = −23→23

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.2518P] where P = (Fo2 + 2Fc2)/3
2511 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
N1	0.2291 (2)	0.28879 (12)	0.65659 (8)	0.0377 (4)
O1	0.2735 (3)	−0.01747 (11)	0.65821 (7)	0.0601 (4)
S1	0.11841 (9)	0.04344 (4)	0.61145 (3)	0.04963 (19)
C1	0.0471 (3)	0.24089 (15)	0.67982 (9)	0.0379 (5)
C2	−0.0702 (3)	0.29706 (17)	0.72559 (10)	0.0470 (5)
H2	−0.0251	0.3672	0.7411	0.056*
C3	−0.2502 (3)	0.2501 (2)	0.74777 (12)	0.0559 (6)
H3	−0.3216	0.2879	0.7794	0.067*
C4	−0.3281 (4)	0.1485 (2)	0.72440 (12)	0.0615 (7)
H4	−0.4534	0.1190	0.7387	0.074*
C5	−0.2173 (3)	0.09217 (19)	0.67984 (11)	0.0553 (6)
H5	−0.2685	0.0235	0.6636	0.066*
C6	−0.0284 (3)	0.13530 (16)	0.65792 (10)	0.0429 (5)
C7	0.3155 (3)	0.25083 (15)	0.59956 (9)	0.0385 (5)
C8	0.4588 (3)	0.31695 (18)	0.56709 (11)	0.0490 (5)
H8	0.4994	0.3865	0.5845	0.059*
C9	0.5405 (4)	0.2812 (2)	0.51022 (12)	0.0613 (6)
H9	0.6383	0.3261	0.4904	0.074*
C10	0.4801 (4)	0.1798 (2)	0.48169 (12)	0.0644 (7)
H10	0.5326	0.1571	0.4423	0.077*
C11	0.3413 (4)	0.11342 (18)	0.51272 (11)	0.0551 (6)
H11	0.3003	0.0447	0.4942	0.066*
C12	0.2605 (3)	0.14667 (16)	0.57131 (10)	0.0424 (5)
C13	0.3051 (3)	0.39597 (15)	0.68456 (10)	0.0400 (5)
H13A	0.4581	0.4007	0.6815	0.048*
H13B	0.2798	0.3974	0.7310	0.048*
C14	0.2012 (3)	0.49772 (15)	0.65152 (9)	0.0380 (5)
C15	0.0249 (4)	0.49180 (19)	0.60717 (11)	0.0571 (6)
H15	−0.0329	0.4223	0.5951	0.068*
C16	−0.0678 (4)	0.5888 (2)	0.58025 (13)	0.0713 (7)
H16	−0.1875	0.5843	0.5503	0.086*
C17	0.0174 (4)	0.6915 (2)	0.59780 (13)	0.0658 (7)
H17	−0.0449	0.7566	0.5799	0.079*
C18	0.1927 (4)	0.69818 (18)	0.64129 (12)	0.0577 (6)
H18	0.2498	0.7679	0.6531	0.069*
C19	0.2860 (3)	0.60252 (16)	0.66792 (10)	0.0470 (5)
H19	0.4072	0.6080	0.6972	0.056*

	U11	U22	U33	U12	U13	U23
N1	0.0403 (9)	0.0307 (9)	0.0428 (9)	0.0004 (8)	0.0072 (7)	0.0001 (7)
O1	0.0760 (11)	0.0362 (8)	0.0685 (10)	0.0096 (8)	0.0085 (9)	0.0108 (7)
S1	0.0607 (4)	0.0344 (3)	0.0537 (4)	−0.0069 (3)	0.0040 (3)	−0.0047 (2)
C1	0.0382 (11)	0.0337 (10)	0.0415 (11)	0.0043 (9)	0.0021 (9)	0.0082 (9)
C2	0.0483 (13)	0.0402 (12)	0.0538 (13)	0.0088 (10)	0.0121 (10)	0.0072 (10)
C3	0.0492 (14)	0.0589 (15)	0.0617 (15)	0.0157 (12)	0.0167 (11)	0.0140 (12)
C4	0.0402 (13)	0.0721 (17)	0.0739 (17)	0.0005 (13)	0.0153 (12)	0.0190 (14)
C5	0.0473 (13)	0.0522 (13)	0.0655 (15)	−0.0094 (11)	−0.0006 (12)	0.0110 (12)
C6	0.0419 (12)	0.0407 (12)	0.0458 (12)	−0.0003 (10)	0.0012 (9)	0.0053 (9)
C7	0.0375 (11)	0.0346 (11)	0.0437 (12)	0.0061 (9)	0.0047 (9)	0.0040 (9)
C8	0.0474 (13)	0.0426 (12)	0.0586 (14)	0.0012 (10)	0.0142 (11)	0.0047 (11)
C9	0.0613 (15)	0.0594 (15)	0.0664 (16)	0.0094 (13)	0.0250 (12)	0.0106 (13)
C10	0.0782 (18)	0.0658 (17)	0.0527 (15)	0.0166 (15)	0.0258 (13)	0.0029 (13)
C11	0.0688 (16)	0.0474 (13)	0.0493 (13)	0.0133 (12)	0.0061 (12)	−0.0056 (11)
C12	0.0449 (12)	0.0386 (11)	0.0435 (12)	0.0064 (10)	0.0032 (9)	0.0025 (9)
C13	0.0406 (11)	0.0351 (11)	0.0441 (11)	−0.0019 (9)	0.0024 (9)	−0.0017 (9)
C14	0.0405 (12)	0.0341 (11)	0.0398 (11)	0.0028 (9)	0.0059 (9)	−0.0015 (9)
C15	0.0581 (15)	0.0467 (13)	0.0640 (15)	−0.0007 (11)	−0.0105 (12)	0.0036 (11)
C16	0.0649 (17)	0.0728 (18)	0.0735 (17)	0.0149 (15)	−0.0109 (13)	0.0165 (15)
C17	0.0839 (19)	0.0470 (15)	0.0682 (16)	0.0211 (14)	0.0174 (15)	0.0187 (12)
C18	0.0831 (18)	0.0347 (12)	0.0580 (14)	0.0000 (12)	0.0225 (13)	0.0035 (11)
C19	0.0572 (14)	0.0402 (12)	0.0443 (12)	−0.0051 (11)	0.0078 (10)	−0.0017 (10)

N1—C1	1.394 (2)	C9—C10	1.381 (3)
N1—C7	1.394 (2)	C9—H9	0.9300
N1—C13	1.463 (2)	C10—C11	1.368 (3)
O1—S1	1.4934 (15)	C10—H10	0.9300
S1—C6	1.756 (2)	C11—C12	1.389 (3)
S1—C12	1.759 (2)	C11—H11	0.9300
C1—C2	1.402 (3)	C13—C14	1.509 (2)
C1—C6	1.405 (3)	C13—H13A	0.9700
C2—C3	1.370 (3)	C13—H13B	0.9700
C2—H2	0.9300	C14—C15	1.372 (3)
C3—C4	1.377 (3)	C14—C19	1.389 (3)
C3—H3	0.9300	C15—C16	1.388 (3)
C4—C5	1.363 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.372 (3)
C5—C6	1.399 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.358 (3)
C7—C12	1.400 (3)	C17—H17	0.9300
C7—C8	1.401 (3)	C18—C19	1.374 (3)
C8—C9	1.370 (3)	C18—H18	0.9300
C8—H8	0.9300	C19—H19	0.9300
C1—N1—C7	122.21 (16)	C11—C10—C9	118.5 (2)
C1—N1—C13	118.50 (15)	C11—C10—H10	120.8
C7—N1—C13	118.04 (15)	C9—C10—H10	120.8
O1—S1—C6	107.77 (9)	C10—C11—C12	121.3 (2)
O1—S1—C12	107.82 (9)	C10—C11—H11	119.3
C6—S1—C12	96.94 (9)	C12—C11—H11	119.3
N1—C1—C2	121.18 (17)	C11—C12—C7	120.65 (19)
N1—C1—C6	121.68 (18)	C11—C12—S1	115.57 (16)
C2—C1—C6	117.14 (18)	C7—C12—S1	123.25 (15)
C3—C2—C1	121.0 (2)	N1—C13—C14	114.44 (15)
C3—C2—H2	119.5	N1—C13—H13A	108.6
C1—C2—H2	119.5	C14—C13—H13A	108.6
C2—C3—C4	121.7 (2)	N1—C13—H13B	108.6
C2—C3—H3	119.1	C14—C13—H13B	108.6
C4—C3—H3	119.1	H13A—C13—H13B	107.6
C5—C4—C3	118.5 (2)	C15—C14—C19	118.54 (18)
C5—C4—H4	120.8	C15—C14—C13	123.23 (17)
C3—C4—H4	120.8	C19—C14—C13	118.22 (17)
C4—C5—C6	121.5 (2)	C14—C15—C16	120.5 (2)
C4—C5—H5	119.3	C14—C15—H15	119.8
C6—C5—H5	119.3	C16—C15—H15	119.8
C5—C6—C1	120.1 (2)	C17—C16—C15	119.9 (2)
C5—C6—S1	115.95 (16)	C17—C16—H16	120.0
C1—C6—S1	123.43 (15)	C15—C16—H16	120.0
N1—C7—C12	121.97 (17)	C18—C17—C16	120.0 (2)
N1—C7—C8	121.10 (18)	C18—C17—H17	120.0
C12—C7—C8	116.93 (19)	C16—C17—H17	120.0
C9—C8—C7	121.4 (2)	C17—C18—C19	120.4 (2)
C9—C8—H8	119.3	C17—C18—H18	119.8
C7—C8—H8	119.3	C19—C18—H18	119.8
C8—C9—C10	121.2 (2)	C18—C19—C14	120.6 (2)
C8—C9—H9	119.4	C18—C19—H19	119.7
C10—C9—H9	119.4	C14—C19—H19	119.7
C7—N1—C1—C2	−162.60 (17)	C7—C8—C9—C10	1.7 (3)
C13—N1—C1—C2	4.4 (3)	C8—C9—C10—C11	−2.1 (4)
C7—N1—C1—C6	16.6 (3)	C9—C10—C11—C12	0.5 (3)
C13—N1—C1—C6	−176.46 (16)	C10—C11—C12—C7	1.5 (3)
N1—C1—C2—C3	179.35 (18)	C10—C11—C12—S1	−170.45 (17)
C6—C1—C2—C3	0.1 (3)	N1—C7—C12—C11	176.90 (18)
C1—C2—C3—C4	−2.6 (3)	C8—C7—C12—C11	−1.8 (3)
C2—C3—C4—C5	2.4 (3)	N1—C7—C12—S1	−11.8 (3)
C3—C4—C5—C6	0.1 (3)	C8—C7—C12—S1	169.48 (15)
C4—C5—C6—C1	−2.5 (3)	O1—S1—C12—C11	90.65 (17)
C4—C5—C6—S1	169.87 (17)	C6—S1—C12—C11	−158.12 (16)
N1—C1—C6—C5	−176.90 (17)	O1—S1—C12—C7	−81.06 (18)
C2—C1—C6—C5	2.3 (3)	C6—S1—C12—C7	30.17 (18)
N1—C1—C6—S1	11.3 (3)	C1—N1—C13—C14	−86.1 (2)
C2—C1—C6—S1	−169.46 (15)	C7—N1—C13—C14	81.4 (2)
O1—S1—C6—C5	−90.78 (17)	N1—C13—C14—C15	11.1 (3)
C12—S1—C6—C5	157.95 (16)	N1—C13—C14—C19	−170.27 (17)
O1—S1—C6—C1	81.32 (17)	C19—C14—C15—C16	−1.0 (3)
C12—S1—C6—C1	−29.95 (18)	C13—C14—C15—C16	177.7 (2)
C1—N1—C7—C12	−16.3 (3)	C14—C15—C16—C17	0.2 (4)
C13—N1—C7—C12	176.65 (16)	C15—C16—C17—C18	0.2 (4)
C1—N1—C7—C8	162.34 (17)	C16—C17—C18—C19	0.1 (4)
C13—N1—C7—C8	−4.7 (3)	C17—C18—C19—C14	−0.9 (3)
N1—C7—C8—C9	−178.49 (19)	C15—C14—C19—C18	1.3 (3)
C12—C7—C8—C9	0.2 (3)	C13—C14—C19—C18	−177.42 (19)

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

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

Symmetry codes: (i) ; (ii) .