10-Ethyl-10H-phenothia-zine-3-carbaldehyde.

In the title mol-ecule, C(15)H(13)NOS, the two benzene rings of the tricyclic fused-ring system are inclined at 21.1 (1)°. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into chains along [001]. The crystal packing also exhibits π-π inter-actions with a distance of 3.801 (5) Å between the centroids of the benzene rings of neighbouring mol-ecules.

Related literature

For related structures, see: Chu & Van der Helm (1975 ▶); Hdii et al. (1998 ▶); Li et al. (2009a ▶,b ▶).

Experimental

Crystal data

C15H13NOS

M = 255.32

Orthorhombic,

a = 8.0867 (1) Å

b = 15.3271 (3) Å

c = 20.3369 (4) Å

V = 2520.67 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.953, T max = 0.976

17210 measured reflections

2225 independent reflections

1909 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.109

S = 1.08

2225 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811047799/cv5184sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047799/cv5184Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047799/cv5184Isup3.cml

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

C15H13NOS	F(000) = 1072
Mr = 255.32	Dx = 1.346 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7387 reflections
a = 8.0867 (1) Å	θ = 2.7–27.1°
b = 15.3271 (3) Å	µ = 0.24 mm−1
c = 20.3369 (4) Å	T = 296 K
V = 2520.67 (8) Å3	Needle, yellow
Z = 8	0.20 × 0.10 × 0.10 mm

Bruker SMART APEX diffractometer	2225 independent reflections
Radiation source: fine-focus sealed tube	1909 reflections with I > 2σ(I)
graphite	Rint = 0.028
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.953, Tmax = 0.976	k = −17→18
17210 measured reflections	l = −22→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.048P)2 + 1.0328P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.030
2225 reflections	Δρmax = 0.40 e Å−3
167 parameters	Δρmin = −0.42 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (8)

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.

	x	y	z	Uiso*/Ueq
S1	0.24520 (8)	0.67345 (3)	0.06193 (3)	0.0654 (2)
C6	0.0560 (2)	0.57828 (11)	0.14810 (8)	0.0434 (4)
N1	0.13723 (18)	0.50268 (9)	0.12517 (7)	0.0460 (4)
C1	0.0870 (2)	0.66009 (11)	0.12020 (9)	0.0473 (4)
C8	0.1974 (2)	0.49538 (11)	0.06126 (8)	0.0415 (4)
O1	0.4535 (2)	0.53800 (12)	−0.16387 (7)	0.0733 (4)
C12	0.3099 (2)	0.56256 (12)	−0.03694 (9)	0.0480 (4)
H12	0.3371	0.6129	−0.0601	0.058*
C11	0.3359 (2)	0.48174 (13)	−0.06591 (8)	0.0488 (4)
C14	0.1335 (2)	0.42393 (12)	0.16677 (10)	0.0541 (5)
H14A	0.1398	0.4419	0.2124	0.065*
H14B	0.2313	0.3894	0.1574	0.065*
C7	0.2448 (2)	0.56995 (11)	0.02515 (9)	0.0434 (4)
C2	0.0052 (3)	0.73369 (13)	0.14222 (10)	0.0583 (5)
H2	0.0247	0.7871	0.1219	0.070*
C5	−0.0556 (2)	0.57511 (13)	0.20039 (10)	0.0554 (5)
H5	−0.0786	0.5219	0.2204	0.066*
C13	0.4132 (3)	0.47568 (17)	−0.13082 (10)	0.0598 (5)
C9	0.2197 (2)	0.41474 (12)	0.03065 (10)	0.0506 (5)
H9	0.1869	0.3643	0.0525	0.061*
C10	0.2888 (2)	0.40786 (13)	−0.03095 (10)	0.0540 (5)
H10	0.3043	0.3530	−0.0495	0.065*
C15	−0.0183 (3)	0.36605 (15)	0.15823 (12)	0.0694 (6)
H15A	−0.1153	0.3976	0.1714	0.104*
H15B	−0.0068	0.3148	0.1850	0.104*
H15C	−0.0282	0.3492	0.1129	0.104*
C4	−0.1325 (3)	0.64997 (17)	0.22290 (11)	0.0677 (6)
H4	−0.2044	0.6465	0.2585	0.081*
C3	−0.1046 (3)	0.72895 (16)	0.19376 (11)	0.0679 (6)
H3	−0.1590	0.7787	0.2085	0.081*
H13	0.429 (4)	0.4148 (18)	−0.1460 (14)	0.102*

	U11	U22	U33	U12	U13	U23
S1	0.0860 (4)	0.0370 (3)	0.0734 (4)	−0.0115 (2)	0.0224 (3)	−0.0011 (2)
C6	0.0406 (9)	0.0475 (10)	0.0421 (9)	0.0007 (7)	−0.0072 (7)	0.0005 (7)
N1	0.0503 (8)	0.0407 (8)	0.0471 (8)	0.0021 (6)	0.0024 (7)	0.0102 (6)
C1	0.0509 (10)	0.0449 (10)	0.0461 (10)	0.0015 (8)	−0.0072 (8)	−0.0011 (8)
C8	0.0400 (8)	0.0382 (9)	0.0464 (9)	−0.0009 (7)	−0.0030 (7)	0.0056 (7)
O1	0.0770 (10)	0.0945 (12)	0.0485 (8)	−0.0086 (9)	0.0078 (7)	−0.0013 (8)
C12	0.0490 (10)	0.0496 (10)	0.0455 (10)	−0.0053 (8)	−0.0021 (8)	0.0086 (8)
C11	0.0427 (10)	0.0585 (12)	0.0453 (10)	0.0012 (8)	−0.0057 (7)	−0.0019 (8)
C14	0.0547 (11)	0.0518 (11)	0.0558 (11)	0.0035 (9)	−0.0008 (9)	0.0213 (8)
C7	0.0452 (10)	0.0373 (9)	0.0476 (10)	−0.0012 (7)	−0.0013 (8)	0.0041 (7)
C2	0.0629 (12)	0.0484 (11)	0.0635 (12)	0.0078 (9)	−0.0119 (10)	−0.0070 (9)
C5	0.0503 (10)	0.0677 (13)	0.0481 (10)	−0.0041 (9)	−0.0001 (9)	0.0016 (9)
C13	0.0505 (11)	0.0781 (15)	0.0508 (11)	0.0003 (11)	−0.0066 (9)	−0.0080 (11)
C9	0.0541 (11)	0.0371 (9)	0.0607 (12)	−0.0007 (8)	0.0000 (9)	0.0055 (8)
C10	0.0545 (11)	0.0474 (11)	0.0600 (12)	0.0036 (9)	−0.0063 (9)	−0.0085 (9)
C15	0.0670 (13)	0.0598 (13)	0.0813 (15)	−0.0072 (10)	0.0038 (11)	0.0263 (11)
C4	0.0539 (12)	0.0902 (17)	0.0589 (12)	0.0050 (11)	0.0047 (10)	−0.0172 (12)
C3	0.0597 (12)	0.0707 (14)	0.0732 (14)	0.0152 (11)	−0.0059 (11)	−0.0206 (12)

S1—C7	1.7538 (18)	C14—H14A	0.9700
S1—C1	1.756 (2)	C14—H14B	0.9700
C6—C5	1.396 (3)	C2—C3	1.376 (3)
C6—C1	1.399 (2)	C2—H2	0.9300
C6—N1	1.411 (2)	C5—C4	1.383 (3)
N1—C8	1.392 (2)	C5—H5	0.9300
N1—C14	1.474 (2)	C13—H13	0.99 (3)
C1—C2	1.382 (3)	C9—C10	1.376 (3)
C8—C9	1.396 (3)	C9—H9	0.9300
C8—C7	1.412 (2)	C10—H10	0.9300
O1—C13	1.212 (3)	C15—H15A	0.9600
C12—C7	1.372 (3)	C15—H15B	0.9600
C12—C11	1.388 (3)	C15—H15C	0.9600
C12—H12	0.9300	C4—C3	1.366 (3)
C11—C10	1.390 (3)	C4—H4	0.9300
C11—C13	1.463 (3)	C3—H3	0.9300
C14—C15	1.524 (3)
C7—S1—C1	100.44 (8)	C3—C2—C1	120.8 (2)
C5—C6—C1	117.13 (17)	C3—C2—H2	119.6
C5—C6—N1	121.61 (16)	C1—C2—H2	119.6
C1—C6—N1	121.24 (16)	C4—C5—C6	120.93 (19)
C8—N1—C6	122.48 (14)	C4—C5—H5	119.5
C8—N1—C14	118.49 (15)	C6—C5—H5	119.5
C6—N1—C14	118.24 (15)	O1—C13—C11	124.4 (2)
C2—C1—C6	120.97 (18)	O1—C13—H13	122.3 (17)
C2—C1—S1	118.17 (15)	C11—C13—H13	113.3 (17)
C6—C1—S1	120.58 (14)	C10—C9—C8	121.78 (17)
N1—C8—C9	122.20 (15)	C10—C9—H9	119.1
N1—C8—C7	121.03 (15)	C8—C9—H9	119.1
C9—C8—C7	116.73 (16)	C9—C10—C11	120.97 (18)
C7—C12—C11	121.50 (17)	C9—C10—H10	119.5
C7—C12—H12	119.3	C11—C10—H10	119.5
C11—C12—H12	119.3	C14—C15—H15A	109.5
C12—C11—C10	117.92 (17)	C14—C15—H15B	109.5
C12—C11—C13	120.29 (19)	H15A—C15—H15B	109.5
C10—C11—C13	121.78 (19)	C14—C15—H15C	109.5
N1—C14—C15	115.30 (16)	H15A—C15—H15C	109.5
N1—C14—H14A	108.4	H15B—C15—H15C	109.5
C15—C14—H14A	108.4	C3—C4—C5	121.2 (2)
N1—C14—H14B	108.4	C3—C4—H4	119.4
C15—C14—H14B	108.4	C5—C4—H4	119.4
H14A—C14—H14B	107.5	C4—C3—C2	118.9 (2)
C12—C7—C8	121.06 (16)	C4—C3—H3	120.5
C12—C7—S1	117.80 (13)	C2—C3—H3	120.5
C8—C7—S1	120.72 (14)
C5—C6—N1—C8	155.35 (17)	N1—C8—C7—C12	177.55 (16)
C1—C6—N1—C8	−26.1 (2)	C9—C8—C7—C12	−0.1 (3)
C5—C6—N1—C14	−14.3 (2)	N1—C8—C7—S1	5.2 (2)
C1—C6—N1—C14	164.21 (16)	C9—C8—C7—S1	−172.52 (13)
C5—C6—C1—C2	−2.4 (3)	C1—S1—C7—C12	157.90 (15)
N1—C6—C1—C2	179.03 (16)	C1—S1—C7—C8	−29.47 (16)
C5—C6—C1—S1	171.37 (14)	C6—C1—C2—C3	2.3 (3)
N1—C6—C1—S1	−7.2 (2)	S1—C1—C2—C3	−171.58 (16)
C7—S1—C1—C2	−155.68 (15)	C1—C6—C5—C4	0.5 (3)
C7—S1—C1—C6	30.42 (16)	N1—C6—C5—C4	179.09 (17)
C6—N1—C8—C9	−155.31 (17)	C12—C11—C13—O1	−2.6 (3)
C14—N1—C8—C9	14.4 (3)	C10—C11—C13—O1	178.44 (19)
C6—N1—C8—C7	27.1 (2)	N1—C8—C9—C10	−175.86 (17)
C14—N1—C8—C7	−163.21 (16)	C7—C8—C9—C10	1.8 (3)
C7—C12—C11—C10	2.1 (3)	C8—C9—C10—C11	−1.5 (3)
C7—C12—C11—C13	−176.89 (17)	C12—C11—C10—C9	−0.5 (3)
C8—N1—C14—C15	−84.5 (2)	C13—C11—C10—C9	178.53 (18)
C6—N1—C14—C15	85.6 (2)	C6—C5—C4—C3	1.5 (3)
C11—C12—C7—C8	−1.8 (3)	C5—C4—C3—C2	−1.6 (3)
C11—C12—C7—S1	170.76 (14)	C1—C2—C3—C4	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1i	0.97	2.64	3.563 (3)	158.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1i	0.97	2.64	3.563 (3)	158

Symmetry code: (i) .