2,3-Diphenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one.

The six-membered thia-zine ring in the title compound, C16H15NOS, adopts a half-chair conformation, with the S atom forming the back of the chair. The base of the chair has a slight twist reflected in the r.m.s. deviation (0.0756 Å) of those five atoms from the plane defined by them. The phenyl substituents are almost perpendicular to each other [dihedral angle 87.06 (9)°]. In the crystal, mol-ecules are linked into chains parallel to the c axis through C-H⋯O inter-actions.

Related literature

For a review of 1,3-thia­zin-4-ones, see: Ryabukhin et al. (1996 ▶). For an unsuccessful attempt to make the title compound, see: Surrey et al. (1958 ▶). For applications of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatri­phospho­rinane-2,4,6-trioxide (T3P) in the synthesis of amide bonds and heterocycles, see: Dunetz et al. (2011 ▶); Unsworth et al. (2013 ▶). For the synthesis and structures of related compounds, see: Yennawar et al. (2013 ▶); Yennawar & Silverberg (2013 ▶).

Experimental

Crystal data

C16H15NOS

M = 269.35

Monoclinic,

a = 13.745 (3) Å

b = 8.240 (2) Å

c = 12.151 (3) Å

β = 100.079 (6)°

V = 1355.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 298 K

0.20 × 0.18 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.956, T max = 0.984

12350 measured reflections

3342 independent reflections

2558 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.140

S = 1.13

3342 reflections

172 parameters

H-atom parameters not refined

Δρmax = 0.31 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT (Bruker, 2001 ▶); 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: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814000324/fy2109sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000324/fy2109Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000324/fy2109Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000324/fy2109Isup4.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H15NOS	F(000) = 568
Mr = 269.35	Dx = 1.320 Mg m−3
Monoclinic, P21/c	Melting point: 369 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.745 (3) Å	Cell parameters from 2176 reflections
b = 8.240 (2) Å	θ = 2.9–24.6°
c = 12.151 (3) Å	µ = 0.23 mm−1
β = 100.079 (6)°	T = 298 K
V = 1355.0 (6) Å3	Block, colorless
Z = 4	0.20 × 0.18 × 0.07 mm

Bruker SMART APEX CCD diffractometer	3342 independent reflections
Radiation source: fine-focus sealed tube	2558 reflections with I > 2σ(I)
Parallel, graphite monochromator	Rint = 0.041
Detector resolution: 8.34 pixels mm-1	θmax = 28.3°, θmin = 2.9°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −10→10
Tmin = 0.956, Tmax = 0.984	l = −16→15
12350 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters not refined
S = 1.13	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.2756P] where P = (Fo2 + 2Fc2)/3
3342 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.18 e Å−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
C1	0.70658 (15)	0.2133 (3)	0.70023 (17)	0.0367 (5)
C2	0.59588 (16)	0.2058 (3)	0.66146 (19)	0.0443 (5)
H2A	0.5705	0.3158	0.6600	0.053*
H2B	0.5838	0.1664	0.5851	0.053*
C3	0.53595 (16)	0.1031 (3)	0.72800 (19)	0.0468 (6)
H3A	0.5481	−0.0110	0.7162	0.056*
H3B	0.4661	0.1239	0.7035	0.056*
C4	0.69656 (14)	0.0797 (2)	0.88595 (16)	0.0306 (4)
H4	0.7313	0.1214	0.9577	0.037*
C5	0.70157 (14)	−0.1039 (2)	0.89528 (16)	0.0317 (4)
C6	0.73750 (16)	−0.2034 (3)	0.8207 (2)	0.0433 (5)
H6	0.7584	−0.1587	0.7585	0.052*
C7	0.74288 (18)	−0.3710 (3)	0.8377 (3)	0.0586 (7)
H7	0.7670	−0.4376	0.7868	0.070*
C8	0.71254 (19)	−0.4369 (3)	0.9293 (3)	0.0625 (8)
H8	0.7166	−0.5484	0.9411	0.075*
C9	0.6762 (2)	−0.3388 (3)	1.0037 (2)	0.0606 (7)
H9	0.6550	−0.3840	1.0655	0.073*
C10	0.67093 (18)	−0.1745 (3)	0.98732 (19)	0.0475 (6)
H10	0.6465	−0.1091	1.0386	0.057*
C11	0.85580 (14)	0.1465 (3)	0.82879 (18)	0.0367 (5)
C12	0.91089 (17)	0.0689 (3)	0.7593 (2)	0.0535 (6)
H12	0.8796	0.0199	0.6936	0.064*
C13	1.0121 (2)	0.0647 (4)	0.7881 (3)	0.0781 (9)
H13	1.0492	0.0118	0.7420	0.094*
C14	1.0589 (2)	0.1379 (5)	0.8843 (3)	0.0823 (11)
H14	1.1274	0.1356	0.9028	0.099*
C15	1.0044 (2)	0.2145 (4)	0.9531 (3)	0.0749 (9)
H15	1.0362	0.2637	1.0185	0.090*
C16	0.90219 (17)	0.2192 (3)	0.9258 (2)	0.0524 (6)
H16	0.8653	0.2711	0.9727	0.063*
N1	0.74904 (11)	0.14718 (19)	0.79997 (13)	0.0316 (4)
O1	0.75623 (12)	0.2813 (2)	0.64049 (14)	0.0575 (5)
S1	0.57039 (4)	0.15171 (7)	0.87256 (5)	0.04271 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0418 (11)	0.0387 (11)	0.0300 (10)	0.0028 (9)	0.0075 (9)	0.0028 (9)
C2	0.0424 (12)	0.0530 (13)	0.0352 (12)	0.0065 (10)	0.0006 (9)	0.0050 (10)
C3	0.0327 (11)	0.0543 (13)	0.0510 (14)	0.0016 (10)	0.0008 (10)	−0.0004 (11)
C4	0.0321 (10)	0.0345 (10)	0.0260 (9)	−0.0025 (8)	0.0073 (8)	−0.0002 (8)
C5	0.0271 (9)	0.0337 (10)	0.0324 (10)	−0.0023 (7)	−0.0001 (8)	0.0023 (8)
C6	0.0378 (11)	0.0417 (12)	0.0525 (14)	−0.0020 (9)	0.0138 (10)	−0.0028 (10)
C7	0.0433 (13)	0.0410 (13)	0.094 (2)	0.0012 (10)	0.0176 (13)	−0.0159 (14)
C8	0.0509 (14)	0.0345 (12)	0.096 (2)	−0.0045 (11)	−0.0033 (14)	0.0155 (14)
C9	0.0751 (19)	0.0483 (15)	0.0552 (16)	−0.0134 (13)	0.0024 (14)	0.0187 (13)
C10	0.0596 (15)	0.0456 (13)	0.0380 (12)	−0.0084 (11)	0.0105 (11)	0.0057 (10)
C11	0.0304 (10)	0.0388 (11)	0.0416 (12)	−0.0023 (8)	0.0079 (8)	0.0100 (9)
C12	0.0406 (13)	0.0620 (16)	0.0622 (16)	−0.0002 (11)	0.0210 (12)	0.0015 (13)
C13	0.0433 (15)	0.101 (2)	0.096 (2)	0.0096 (15)	0.0308 (16)	0.016 (2)
C14	0.0302 (13)	0.116 (3)	0.100 (3)	−0.0001 (15)	0.0103 (16)	0.032 (2)
C15	0.0471 (16)	0.099 (2)	0.071 (2)	−0.0182 (16)	−0.0107 (14)	0.0139 (17)
C16	0.0413 (13)	0.0632 (16)	0.0502 (14)	−0.0058 (11)	0.0010 (11)	0.0036 (12)
N1	0.0297 (8)	0.0362 (9)	0.0296 (8)	−0.0012 (7)	0.0073 (6)	0.0046 (7)
O1	0.0549 (10)	0.0746 (12)	0.0447 (10)	−0.0011 (9)	0.0138 (8)	0.0237 (9)
S1	0.0376 (3)	0.0476 (3)	0.0466 (3)	0.0076 (2)	0.0176 (2)	0.0004 (3)

C1—O1	1.217 (2)	C7—H7	0.9300
C1—N1	1.363 (3)	C8—C9	1.370 (4)
C1—C2	1.513 (3)	C8—H8	0.9300
C2—C3	1.511 (3)	C9—C10	1.368 (3)
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700	C10—H10	0.9300
C3—S1	1.783 (2)	C11—C16	1.376 (3)
C3—H3A	0.9700	C11—C12	1.385 (3)
C3—H3B	0.9700	C11—N1	1.448 (2)
C4—N1	1.478 (2)	C12—C13	1.374 (4)
C4—C5	1.518 (3)	C12—H12	0.9300
C4—S1	1.813 (2)	C13—C14	1.371 (5)
C4—H4	0.9800	C13—H13	0.9300
C5—C6	1.377 (3)	C14—C15	1.370 (5)
C5—C10	1.390 (3)	C14—H14	0.9300
C6—C7	1.396 (3)	C15—C16	1.387 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.368 (4)	C16—H16	0.9300
O1—C1—N1	121.12 (19)	C7—C8—H8	120.0
O1—C1—C2	118.13 (19)	C9—C8—H8	120.0
N1—C1—C2	120.75 (18)	C10—C9—C8	120.3 (2)
C3—C2—C1	117.96 (18)	C10—C9—H9	119.9
C3—C2—H2A	107.8	C8—C9—H9	119.9
C1—C2—H2A	107.8	C9—C10—C5	121.0 (2)
C3—C2—H2B	107.8	C9—C10—H10	119.5
C1—C2—H2B	107.8	C5—C10—H10	119.5
H2A—C2—H2B	107.2	C16—C11—C12	120.2 (2)
C2—C3—S1	109.00 (16)	C16—C11—N1	120.3 (2)
C2—C3—H3A	109.9	C12—C11—N1	119.6 (2)
S1—C3—H3A	109.9	C13—C12—C11	119.6 (3)
C2—C3—H3B	109.9	C13—C12—H12	120.2
S1—C3—H3B	109.9	C11—C12—H12	120.2
H3A—C3—H3B	108.3	C14—C13—C12	120.6 (3)
N1—C4—C5	113.97 (16)	C14—C13—H13	119.7
N1—C4—S1	113.02 (13)	C12—C13—H13	119.7
C5—C4—S1	111.29 (13)	C15—C14—C13	119.9 (3)
N1—C4—H4	105.9	C15—C14—H14	120.1
C5—C4—H4	105.9	C13—C14—H14	120.1
S1—C4—H4	105.9	C14—C15—C16	120.4 (3)
C6—C5—C10	118.4 (2)	C14—C15—H15	119.8
C6—C5—C4	124.14 (19)	C16—C15—H15	119.8
C10—C5—C4	117.46 (18)	C11—C16—C15	119.4 (3)
C5—C6—C7	120.5 (2)	C11—C16—H16	120.3
C5—C6—H6	119.8	C15—C16—H16	120.3
C7—C6—H6	119.8	C1—N1—C11	118.34 (16)
C8—C7—C6	119.8 (2)	C1—N1—C4	126.35 (16)
C8—C7—H7	120.1	C11—N1—C4	115.27 (15)
C6—C7—H7	120.1	C3—S1—C4	95.72 (10)
C7—C8—C9	120.0 (2)
O1—C1—C2—C3	172.2 (2)	C13—C14—C15—C16	−0.3 (5)
N1—C1—C2—C3	−8.5 (3)	C12—C11—C16—C15	0.2 (4)
C1—C2—C3—S1	49.0 (2)	N1—C11—C16—C15	178.7 (2)
N1—C4—C5—C6	−9.7 (3)	C14—C15—C16—C11	−0.1 (4)
S1—C4—C5—C6	119.51 (19)	O1—C1—N1—C11	−5.6 (3)
N1—C4—C5—C10	167.98 (17)	C2—C1—N1—C11	175.19 (19)
S1—C4—C5—C10	−62.8 (2)	O1—C1—N1—C4	172.0 (2)
C10—C5—C6—C7	−0.1 (3)	C2—C1—N1—C4	−7.2 (3)
C4—C5—C6—C7	177.6 (2)	C16—C11—N1—C1	122.7 (2)
C5—C6—C7—C8	−0.2 (4)	C12—C11—N1—C1	−58.8 (3)
C6—C7—C8—C9	0.5 (4)	C16—C11—N1—C4	−55.1 (3)
C7—C8—C9—C10	−0.6 (4)	C12—C11—N1—C4	123.4 (2)
C8—C9—C10—C5	0.3 (4)	C5—C4—N1—C1	108.3 (2)
C6—C5—C10—C9	0.0 (3)	S1—C4—N1—C1	−20.1 (2)
C4—C5—C10—C9	−177.9 (2)	C5—C4—N1—C11	−74.1 (2)
C16—C11—C12—C13	0.2 (4)	S1—C4—N1—C11	157.54 (14)
N1—C11—C12—C13	−178.4 (2)	C2—C3—S1—C4	−64.60 (17)
C11—C12—C13—C14	−0.6 (4)	N1—C4—S1—C3	51.31 (16)
C12—C13—C14—C15	0.7 (5)	C5—C4—S1—C3	−78.43 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.98	2.33	3.265 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.98	2.33	3.265 (3)	159

Symmetry code: (i) .