10-(Prop-2-yn-yl)-10H-phenothia-zine.

In the mol-ecule of the title compound, C(15)H(11)NS, the butterfly angle between the two planes defined by the two wings of the phenothia-zine unit is 33.5 (8)°. The dihedral angles between the two benzene rings and the propynyl group are 85 (4) and 63 (4)°.

Related literature

For the 1,3-dipolar addition reaction in chemical synthesis, see: Kumar et al. (2006 ▶); Kalita et al. (2006 ▶); Sibi et al. (2006 ▶); Choi et al. (2006 ▶); Ji-Cai et al. (2007 ▶); Aouine et al. (2008 ▶).

Experimental

Crystal data

C15H11NS

M = 237.31

Monoclinic,

a = 10.5306 (10) Å

b = 7.2981 (6) Å

c = 15.6782 (14) Å

β = 96.023 (3)°

V = 1198.27 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.42 × 0.38 × 0.17 mm

Data collection

Bruker APEXII CCD detector diffractometer

16905 measured reflections

3688 independent reflections

2683 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.151

S = 1.08

3688 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040638/ds2063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040638/ds2063Isup2.hkl

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

C15H11NS	F(000) = 496
Mr = 237.31	Dx = 1.315 Mg m−3
Monoclinic, P21/n	Melting point: 355 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.5306 (10) Å	Cell parameters from 2646 reflections
b = 7.2981 (6) Å	θ = 1.7–26.2°
c = 15.6782 (14) Å	µ = 0.24 mm−1
β = 96.023 (3)°	T = 296 K
V = 1198.27 (18) Å3	Block, colourless
Z = 4	0.42 × 0.38 × 0.17 mm

Bruker APEXII CCD detector diffractometer	2683 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 30.6°, θmin = 2.2°
ω and φ scans	h = −15→15
16905 measured reflections	k = −10→10
3688 independent reflections	l = −21→22

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.0829P)2 + 0.0989P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.002
3688 reflections	Δρmax = 0.35 e Å−3
155 parameters	Δρmin = −0.24 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: 0.015 (3)

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	0.74384 (5)	1.23619 (6)	1.08918 (3)	0.06194 (18)
C1	0.64205 (14)	1.18256 (18)	0.99624 (9)	0.0453 (3)
C12	0.81567 (13)	1.0206 (2)	1.10752 (9)	0.0476 (3)
C6	0.68419 (12)	1.06413 (17)	0.93508 (8)	0.0409 (3)
C7	0.84191 (12)	0.9120 (2)	1.03762 (8)	0.0444 (3)
C5	0.60793 (14)	1.0439 (2)	0.85724 (9)	0.0482 (3)
H5	0.6338	0.9661	0.8154	0.058*
C4	0.49414 (14)	1.1390 (2)	0.84205 (11)	0.0572 (4)
H4	0.4464	1.1286	0.7889	0.069*
C3	0.45030 (16)	1.2484 (2)	0.90383 (12)	0.0594 (4)
H3	0.3724	1.3087	0.8935	0.071*
C14	0.78307 (14)	0.6913 (2)	0.86512 (9)	0.0512 (3)
C2	0.52371 (17)	1.26762 (19)	0.98158 (11)	0.0545 (4)
H2	0.4937	1.3382	1.0246	0.065*
C13	0.84863 (13)	0.8676 (2)	0.88310 (9)	0.0504 (3)
H13A	0.9391	0.8445	0.8970	0.060*
H13B	0.8386	0.9419	0.8315	0.060*
C8	0.90857 (15)	0.7493 (2)	1.05489 (11)	0.0582 (4)
H8	0.9266	0.6740	1.0099	0.070*
C10	0.91968 (17)	0.8038 (3)	1.20672 (11)	0.0690 (5)
H10	0.9457	0.7676	1.2627	0.083*
C11	0.85181 (15)	0.9640 (3)	1.19087 (10)	0.0585 (4)
H11	0.8301	1.0346	1.2365	0.070*
C15	0.72916 (18)	0.5503 (3)	0.85403 (11)	0.0663 (4)
H15	0.6866	0.4391	0.8453	0.080*
C9	0.94833 (17)	0.6984 (3)	1.13868 (12)	0.0707 (5)
H9	0.9952	0.5912	1.1490	0.085*
N1	0.80200 (10)	0.97117 (16)	0.95310 (7)	0.0436 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0868 (3)	0.0449 (2)	0.0533 (3)	−0.00690 (19)	0.0031 (2)	−0.01417 (16)
C1	0.0585 (8)	0.0314 (6)	0.0470 (7)	−0.0052 (5)	0.0096 (6)	0.0007 (5)
C12	0.0450 (6)	0.0521 (8)	0.0449 (7)	−0.0122 (6)	0.0006 (5)	−0.0051 (6)
C6	0.0473 (6)	0.0334 (6)	0.0426 (6)	−0.0073 (5)	0.0075 (5)	0.0020 (5)
C7	0.0374 (6)	0.0507 (8)	0.0447 (7)	−0.0080 (5)	0.0033 (5)	−0.0021 (6)
C5	0.0555 (8)	0.0423 (7)	0.0463 (7)	−0.0043 (6)	0.0027 (6)	0.0008 (6)
C4	0.0575 (8)	0.0522 (9)	0.0595 (9)	−0.0032 (7)	−0.0053 (7)	0.0091 (7)
C3	0.0560 (8)	0.0437 (8)	0.0788 (11)	0.0036 (6)	0.0088 (8)	0.0134 (7)
C14	0.0540 (8)	0.0558 (9)	0.0452 (7)	0.0055 (7)	0.0118 (6)	−0.0064 (6)
C2	0.0685 (9)	0.0341 (7)	0.0638 (9)	0.0034 (6)	0.0202 (8)	0.0038 (6)
C13	0.0456 (7)	0.0608 (9)	0.0469 (7)	−0.0033 (6)	0.0150 (6)	−0.0047 (6)
C8	0.0486 (7)	0.0684 (11)	0.0566 (9)	0.0095 (7)	0.0013 (6)	−0.0029 (7)
C10	0.0587 (9)	0.0943 (14)	0.0512 (9)	0.0004 (9)	−0.0072 (7)	0.0113 (9)
C11	0.0553 (8)	0.0759 (11)	0.0434 (7)	−0.0118 (8)	0.0008 (6)	−0.0050 (7)
C15	0.0830 (12)	0.0568 (10)	0.0602 (10)	−0.0058 (9)	0.0134 (8)	−0.0081 (8)
C9	0.0587 (9)	0.0832 (12)	0.0681 (11)	0.0157 (9)	−0.0038 (8)	0.0121 (10)
N1	0.0435 (6)	0.0475 (6)	0.0402 (6)	−0.0038 (5)	0.0066 (4)	−0.0041 (5)

S1—C12	1.7563 (17)	C3—H3	0.9300
S1—C1	1.7599 (15)	C14—C15	1.179 (2)
C1—C2	1.390 (2)	C14—C13	1.473 (2)
C1—C6	1.3974 (19)	C2—H2	0.9300
C12—C11	1.385 (2)	C13—N1	1.4594 (16)
C12—C7	1.4034 (19)	C13—H13A	0.9700
C6—C5	1.3965 (19)	C13—H13B	0.9700
C6—N1	1.4162 (17)	C8—C9	1.387 (2)
C7—C8	1.391 (2)	C8—H8	0.9300
C7—N1	1.4151 (17)	C10—C9	1.374 (3)
C5—C4	1.384 (2)	C10—C11	1.379 (3)
C5—H5	0.9300	C10—H10	0.9300
C4—C3	1.372 (2)	C11—H11	0.9300
C4—H4	0.9300	C15—H15	0.9300
C3—C2	1.380 (3)	C9—H9	0.9300
C12—S1—C1	98.67 (7)	C3—C2—H2	119.7
C2—C1—C6	120.44 (14)	C1—C2—H2	119.7
C2—C1—S1	119.69 (12)	N1—C13—C14	114.10 (11)
C6—C1—S1	119.73 (11)	N1—C13—H13A	108.7
C11—C12—C7	120.73 (15)	C14—C13—H13A	108.7
C11—C12—S1	119.52 (12)	N1—C13—H13B	108.7
C7—C12—S1	119.66 (11)	C14—C13—H13B	108.7
C5—C6—C1	118.04 (13)	H13A—C13—H13B	107.6
C5—C6—N1	122.35 (12)	C9—C8—C7	120.59 (16)
C1—C6—N1	119.61 (12)	C9—C8—H8	119.7
C8—C7—C12	117.82 (14)	C7—C8—H8	119.7
C8—C7—N1	122.48 (13)	C9—C10—C11	119.11 (16)
C12—C7—N1	119.70 (13)	C9—C10—H10	120.4
C4—C5—C6	120.38 (14)	C11—C10—H10	120.4
C4—C5—H5	119.8	C10—C11—C12	120.58 (16)
C6—C5—H5	119.8	C10—C11—H11	119.7
C3—C4—C5	121.32 (15)	C12—C11—H11	119.7
C3—C4—H4	119.3	C14—C15—H15	180.0
C5—C4—H4	119.3	C10—C9—C8	121.09 (18)
C4—C3—C2	118.93 (15)	C10—C9—H9	119.5
C4—C3—H3	120.5	C8—C9—H9	119.5
C2—C3—H3	120.5	C7—N1—C6	120.06 (10)
C15—C14—C13	177.31 (16)	C7—N1—C13	117.11 (12)
C3—C2—C1	120.68 (15)	C6—N1—C13	117.06 (11)