10-(Prop-1-yn-1-yl)-10H-phenothia-zine.

In the title compound, C(15)H(11)NS, the asymmetric unit comprises one half-mol-ecule; a mirror plane passes through the S atom, the ynamine fragment, the methyl C atom and one methyl H atom. The phenothia-zine moiety has a butterfly conformation and the central six-membered ring has a boat conformation. The dihedral angle between the benzene rings is 149.40 (4)°. The crystal structure is stabilized by van der Waals inter-actions.

Related literature

For related structures of phenothia­zine compounds, see: Okuno et al. (2006 ▶); Tabata & Okuno (2012 ▶). For the preparation of the title compound, see: Zaugg et al. (1958 ▶).

Experimental

Crystal data

C15H11NS

M = 237.31

Orthorhombic,

a = 14.717 (6) Å

b = 10.631 (4) Å

c = 7.375 (3) Å

V = 1153.9 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 93 K

0.12 × 0.10 × 0.08 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: numerical (NUMABS; Rigaku, 1999 ▶) T min = 0.959, T max = 0.980

4889 measured reflections

1486 independent reflections

1441 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.065

S = 1.08

1486 reflections

87 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 670 Friedel pairs

Flack parameter: −0.01 (6)

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036537/bx2425sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036537/bx2425Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036537/bx2425Isup3.cml

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

C15H11NS	F(000) = 496
Mr = 237.31	Dx = 1.366 Mg m−3
Orthorhombic, Cmc21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: C 2c -2	Cell parameters from 2342 reflections
a = 14.717 (6) Å	θ = 2.4–31.2°
b = 10.631 (4) Å	µ = 0.25 mm−1
c = 7.375 (3) Å	T = 93 K
V = 1153.9 (8) Å3	Block, colorless
Z = 4	0.12 × 0.10 × 0.08 mm

Rigaku Saturn724+ diffractometer	1441 reflections with I > 2σ(I)
Detector resolution: 28.445 pixels mm-1	Rint = 0.019
ω scans	θmax = 28.5°, θmin = 2.4°
Absorption correction: numerical (NUMABS; Rigaku, 1999)	h = −19→16
Tmin = 0.959, Tmax = 0.980	k = −14→12
4889 measured reflections	l = −9→9
1486 independent reflections

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)] = 0.025	H-atom parameters constrained
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0354P)2 + 0.514P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1486 reflections	Δρmax = 0.20 e Å−3
87 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 670 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (6)

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
S1	0.0000	0.03514 (4)	−0.00174 (4)	0.01839 (11)
N1	0.0000	0.28986 (13)	0.1771 (2)	0.0165 (3)
C1	0.08381 (8)	0.22366 (10)	0.19225 (16)	0.0153 (2)
C2	0.15834 (8)	0.27842 (11)	0.27878 (17)	0.0176 (2)
H2	0.1524	0.3585	0.3346	0.021*
C3	0.24154 (8)	0.21576 (12)	0.28336 (18)	0.0201 (3)
H3	0.2926	0.2542	0.3393	0.024*
C4	0.24978 (8)	0.09669 (12)	0.20594 (18)	0.0212 (3)
H4	0.3067	0.0545	0.2075	0.025*
C5	0.17460 (9)	0.03964 (11)	0.12637 (17)	0.0189 (3)
H5	0.1797	−0.0430	0.0783	0.023*
C6	0.09172 (8)	0.10329 (11)	0.11690 (15)	0.0163 (2)
C7	0.0000	0.41727 (16)	0.1900 (2)	0.0164 (3)
C8	0.0000	0.52987 (15)	0.1916 (3)	0.0171 (3)
C9	0.0000	0.66718 (16)	0.1911 (3)	0.0218 (4)
H9A	0.0000	0.7026	0.3042	0.045 (8)*
H9B	−0.0435	0.7017	0.1183	0.050 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0226 (2)	0.01654 (18)	0.01607 (19)	0.000	0.000	−0.00403 (15)
N1	0.0160 (7)	0.0124 (6)	0.0212 (7)	0.000	0.000	−0.0023 (5)
C1	0.0150 (5)	0.0154 (5)	0.0155 (5)	0.0004 (4)	0.0028 (4)	0.0021 (4)
C2	0.0188 (6)	0.0159 (5)	0.0180 (5)	−0.0016 (5)	0.0009 (5)	0.0001 (4)
C3	0.0165 (6)	0.0225 (6)	0.0212 (6)	−0.0021 (5)	0.0001 (5)	0.0039 (4)
C4	0.0178 (5)	0.0209 (6)	0.0249 (6)	0.0043 (5)	0.0040 (5)	0.0060 (5)
C5	0.0218 (6)	0.0159 (5)	0.0189 (6)	0.0030 (4)	0.0061 (5)	0.0021 (4)
C6	0.0183 (5)	0.0160 (5)	0.0144 (5)	−0.0007 (4)	0.0027 (4)	0.0011 (4)
C7	0.0146 (7)	0.0172 (8)	0.0175 (7)	0.000	0.000	−0.0018 (6)
C8	0.0143 (7)	0.0165 (8)	0.0206 (8)	0.000	0.000	−0.0014 (6)
C9	0.0232 (9)	0.0142 (7)	0.0278 (9)	0.000	0.000	−0.0011 (7)

S1—C6i	1.7642 (13)	C3—H3	0.9500
S1—C6	1.7643 (13)	C4—C5	1.3914 (19)
N1—C7	1.358 (2)	C4—H4	0.9500
N1—C1	1.4246 (14)	C5—C6	1.3966 (17)
N1—C1i	1.4246 (14)	C5—H5	0.9500
C1—C2	1.3961 (17)	C7—C8	1.197 (3)
C1—C6	1.3999 (17)	C8—C9	1.460 (2)
C2—C3	1.3944 (17)	C9—H9A	0.9152
C2—H2	0.9500	C9—H9B	0.9126
C3—C4	1.3940 (18)
C6i—S1—C6	99.84 (8)	C5—C4—H4	120.0
C7—N1—C1	119.16 (7)	C3—C4—H4	120.0
C7—N1—C1i	119.16 (7)	C4—C5—C6	120.29 (11)
C1—N1—C1i	119.97 (14)	C4—C5—H5	119.9
C2—C1—C6	119.82 (11)	C6—C5—H5	119.9
C2—C1—N1	120.67 (11)	C5—C6—C1	119.71 (11)
C6—C1—N1	119.50 (11)	C5—C6—S1	119.61 (9)
C3—C2—C1	120.12 (11)	C1—C6—S1	120.57 (9)
C3—C2—H2	119.9	C8—C7—N1	176.53 (19)
C1—C2—H2	119.9	C7—C8—C9	179.3 (2)
C4—C3—C2	120.02 (11)	C8—C9—H9A	114.2
C4—C3—H3	120.0	C8—C9—H9B	113.8
C2—C3—H3	120.0	H9A—C9—H9B	111.8
C5—C4—C3	119.96 (11)
C7—N1—C1—C2	21.9 (2)	C4—C5—C6—S1	174.51 (9)
C1i—N1—C1—C2	−143.06 (11)	C2—C1—C6—C5	−1.00 (17)
C7—N1—C1—C6	−157.02 (14)	N1—C1—C6—C5	177.97 (12)
C1i—N1—C1—C6	38.0 (2)	C2—C1—C6—S1	−177.19 (9)
C6—C1—C2—C3	2.76 (17)	N1—C1—C6—S1	1.78 (15)
N1—C1—C2—C3	−176.20 (12)	C6i—S1—C6—C5	152.23 (7)
C1—C2—C3—C4	−1.81 (18)	C6i—S1—C6—C1	−31.58 (13)
C2—C3—C4—C5	−0.91 (18)	C1—N1—C7—C8	97.44 (13)
C3—C4—C5—C6	2.68 (18)	C1i—N1—C7—C8	−97.44 (13)
C4—C5—C6—C1	−1.72 (18)	N1—C7—C8—C9	0.00 (5)