2,3-Diphenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

In the title compound, C20H15NOS, the dihedral angle between the phenyl rings is 74.25 (6)°. The six-membered 1,3-thia-zine ring has an envelope conformation with the C atom at the 2-position forming the flap. The crystal structure features weak C-H⋯O inter-actions, which lead to the formation of a tape motif along [110].

Related literature

For other preparations of the title compound, see: Ponci et al. (1963 ▶); Kollenz & Ziegler (1970 ▶); Oae & Numata (1974 ▶); Badea et al. (1998 ▶). For previously published methods for the preparation of 1,3-thiazin-4-ones by condensation of an imine with a thio­acid, see: Kamel et al. (2010 ▶); Zarghi et al. (2009 ▶); Zhou et al. (2008 ▶); Srivastava et al. (2002 ▶). For the synthesis and crystal structures of related compounds, see: Yennawar & Silverberg (2013 ▶, 2014 ▶); Yennawar et al. (2013 ▶).

Experimental

Crystal data

C20H15NOS

M = 317.39

Monoclinic,

a = 14.799 (4) Å

b = 9.606 (3) Å

c = 22.492 (6) Å

β = 98.736 (5)°

V = 3160.1 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 298 K

0.18 × 0.16 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.963, T max = 0.990

14747 measured reflections

3956 independent reflections

3300 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.127

S = 1.06

3956 reflections

208 parameters

H-atom parameters not refined

Δρmax = 0.28 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2001 ▶); 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: XSHELL in SHELXTL (Sheldrick, 2008) ▶; software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814005881/fy2112sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005881/fy2112Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005881/fy2112Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005881/fy2112Isup4.cml

CCDC reference: 992181

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

C20H15NOS	F(000) = 1328
Mr = 317.39	Dx = 1.334 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.799 (4) Å	Cell parameters from 4538 reflections
b = 9.606 (3) Å	θ = 2.5–28.0°
c = 22.492 (6) Å	µ = 0.21 mm−1
β = 98.736 (5)°	T = 298 K
V = 3160.1 (15) Å3	Block, colourless
Z = 8	0.18 × 0.16 × 0.05 mm

Bruker SMART APEX CCD area-detector diffractometer	3956 independent reflections
Radiation source: fine-focus sealed tube	3300 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.34 pixels mm-1	θmax = 28.4°, θmin = 1.8°
φ and ω scans	h = −18→19
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −12→12
Tmin = 0.963, Tmax = 0.990	l = −30→30
14747 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters not refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0565P)2 + 1.8423P] where P = (Fo2 + 2Fc2)/3
3956 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 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	0.03935 (11)	0.32561 (17)	0.11547 (7)	0.0434 (4)
C2	0.01411 (11)	0.46594 (17)	0.13594 (7)	0.0434 (4)
C3	0.04910 (12)	0.58978 (17)	0.11600 (7)	0.0460 (4)
C4	0.18665 (11)	0.42745 (15)	0.09649 (7)	0.0406 (3)
H4	0.2301	0.4022	0.0695	0.049*
C5	0.24251 (10)	0.45006 (15)	0.15831 (7)	0.0377 (3)
C6	0.23025 (12)	0.37177 (17)	0.20814 (8)	0.0469 (4)
H6	0.1848	0.3041	0.2048	0.056*
C7	0.28512 (13)	0.3933 (2)	0.26298 (8)	0.0557 (4)
H7	0.2759	0.3408	0.2963	0.067*
C8	0.35351 (13)	0.4925 (2)	0.26842 (9)	0.0559 (4)
H8	0.3903	0.5069	0.3052	0.067*
C9	0.36669 (12)	0.56958 (17)	0.21908 (9)	0.0519 (4)
H9	0.4131	0.6357	0.2225	0.062*
C10	0.31166 (11)	0.54979 (16)	0.16442 (8)	0.0442 (4)
H10	0.3208	0.6034	0.1314	0.053*
C11	0.14103 (11)	0.18738 (16)	0.06409 (7)	0.0393 (3)
C12	0.21265 (16)	0.1052 (2)	0.08852 (9)	0.0657 (6)
H12	0.2492	0.1317	0.1241	0.079*
C13	0.23063 (18)	−0.0177 (2)	0.06018 (10)	0.0759 (7)
H13	0.2795	−0.0733	0.0767	0.091*
C14	0.17703 (15)	−0.05742 (19)	0.00829 (9)	0.0592 (5)
H14	0.1882	−0.1412	−0.0100	0.071*
C15	0.10730 (15)	0.0256 (2)	−0.01663 (9)	0.0670 (6)
H15	0.0715	−0.0005	−0.0525	0.080*
C16	0.08922 (14)	0.1488 (2)	0.01100 (8)	0.0603 (5)
H16	0.0417	0.2057	−0.0065	0.072*
C17	−0.05168 (12)	0.4728 (2)	0.17424 (8)	0.0514 (4)
H17	−0.0753	0.3909	0.1877	0.062*
C18	−0.08209 (14)	0.5990 (2)	0.19226 (9)	0.0619 (5)
H18	−0.1253	0.6023	0.2182	0.074*
C19	−0.04820 (14)	0.7204 (2)	0.17166 (10)	0.0660 (6)
H19	−0.0696	0.8056	0.1834	0.079*
C20	0.01695 (14)	0.7175 (2)	0.13392 (9)	0.0583 (5)
H20	0.0394	0.8002	0.1204	0.070*
N1	0.12016 (9)	0.31448 (13)	0.09313 (6)	0.0408 (3)
O1	−0.01007 (9)	0.22507 (14)	0.11818 (6)	0.0617 (4)
S1	0.13067 (3)	0.58704 (5)	0.06672 (2)	0.05412 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0430 (9)	0.0427 (8)	0.0451 (8)	−0.0043 (7)	0.0089 (7)	−0.0052 (7)
C2	0.0396 (8)	0.0446 (9)	0.0443 (8)	0.0026 (7)	0.0007 (6)	−0.0060 (7)
C3	0.0447 (9)	0.0441 (9)	0.0454 (8)	0.0056 (7)	−0.0049 (7)	−0.0001 (7)
C4	0.0427 (8)	0.0361 (7)	0.0449 (8)	−0.0027 (6)	0.0124 (6)	0.0006 (6)
C5	0.0369 (8)	0.0311 (7)	0.0464 (8)	0.0018 (6)	0.0104 (6)	−0.0028 (6)
C6	0.0459 (9)	0.0435 (8)	0.0521 (9)	−0.0045 (7)	0.0107 (7)	0.0021 (7)
C7	0.0616 (11)	0.0576 (11)	0.0474 (9)	0.0031 (9)	0.0071 (8)	0.0055 (8)
C8	0.0561 (11)	0.0523 (10)	0.0555 (10)	0.0068 (9)	−0.0038 (8)	−0.0108 (8)
C9	0.0457 (9)	0.0382 (8)	0.0700 (11)	−0.0023 (7)	0.0033 (8)	−0.0101 (8)
C10	0.0457 (9)	0.0332 (7)	0.0552 (9)	−0.0018 (6)	0.0119 (7)	−0.0009 (7)
C11	0.0436 (8)	0.0360 (7)	0.0396 (7)	−0.0032 (6)	0.0111 (6)	−0.0018 (6)
C12	0.0748 (14)	0.0642 (12)	0.0528 (10)	0.0207 (10)	−0.0070 (9)	−0.0110 (9)
C13	0.1004 (18)	0.0631 (13)	0.0624 (12)	0.0353 (12)	0.0069 (12)	0.0007 (10)
C14	0.0841 (14)	0.0400 (9)	0.0607 (11)	−0.0032 (9)	0.0341 (10)	−0.0072 (8)
C15	0.0679 (13)	0.0740 (14)	0.0582 (11)	−0.0013 (11)	0.0070 (9)	−0.0278 (10)
C16	0.0606 (11)	0.0658 (12)	0.0513 (10)	0.0133 (10)	−0.0021 (8)	−0.0166 (9)
C17	0.0438 (9)	0.0568 (10)	0.0531 (9)	0.0044 (8)	0.0058 (7)	−0.0069 (8)
C18	0.0518 (11)	0.0707 (13)	0.0622 (11)	0.0164 (9)	0.0056 (9)	−0.0137 (10)
C19	0.0635 (12)	0.0582 (11)	0.0713 (12)	0.0262 (10)	−0.0057 (10)	−0.0156 (10)
C20	0.0636 (12)	0.0425 (9)	0.0630 (11)	0.0104 (8)	−0.0094 (9)	−0.0011 (8)
N1	0.0424 (7)	0.0363 (6)	0.0447 (7)	−0.0045 (5)	0.0101 (5)	−0.0051 (5)
O1	0.0595 (8)	0.0514 (7)	0.0800 (9)	−0.0190 (6)	0.0296 (7)	−0.0166 (6)
S1	0.0616 (3)	0.0450 (2)	0.0554 (3)	−0.0003 (2)	0.0080 (2)	0.01415 (18)

C1—O1	1.218 (2)	C10—H10	0.9300
C1—N1	1.370 (2)	C11—C12	1.368 (2)
C1—C2	1.490 (2)	C11—C16	1.368 (2)
C2—C17	1.396 (2)	C11—N1	1.4401 (19)
C2—C3	1.398 (2)	C12—C13	1.386 (3)
C3—C20	1.397 (2)	C12—H12	0.9300
C3—S1	1.7587 (19)	C13—C14	1.362 (3)
C4—N1	1.4590 (19)	C13—H13	0.9300
C4—C5	1.521 (2)	C14—C15	1.356 (3)
C4—S1	1.8211 (16)	C14—H14	0.9300
C4—H4	0.9800	C15—C16	1.382 (3)
C5—C6	1.384 (2)	C15—H15	0.9300
C5—C10	1.393 (2)	C16—H16	0.9300
C6—C7	1.385 (2)	C17—C18	1.376 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.382 (3)	C18—C19	1.377 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.373 (3)	C19—C20	1.378 (3)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.381 (2)	C20—H20	0.9300
C9—H9	0.9300
O1—C1—N1	121.37 (15)	C12—C11—N1	120.90 (15)
O1—C1—C2	121.40 (15)	C16—C11—N1	119.66 (15)
N1—C1—C2	117.23 (14)	C11—C12—C13	119.86 (18)
C17—C2—C3	119.01 (16)	C11—C12—H12	120.1
C17—C2—C1	117.65 (15)	C13—C12—H12	120.1
C3—C2—C1	123.24 (15)	C14—C13—C12	120.3 (2)
C20—C3—C2	119.70 (17)	C14—C13—H13	119.8
C20—C3—S1	119.44 (14)	C12—C13—H13	119.8
C2—C3—S1	120.83 (13)	C15—C14—C13	119.79 (18)
N1—C4—C5	114.97 (12)	C15—C14—H14	120.1
N1—C4—S1	109.96 (11)	C13—C14—H14	120.1
C5—C4—S1	111.69 (10)	C14—C15—C16	120.32 (18)
N1—C4—H4	106.6	C14—C15—H15	119.8
C5—C4—H4	106.6	C16—C15—H15	119.8
S1—C4—H4	106.6	C11—C16—C15	120.21 (18)
C6—C5—C10	118.58 (15)	C11—C16—H16	119.9
C6—C5—C4	122.85 (14)	C15—C16—H16	119.9
C10—C5—C4	118.51 (14)	C18—C17—C2	120.88 (19)
C5—C6—C7	120.57 (16)	C18—C17—H17	119.6
C5—C6—H6	119.7	C2—C17—H17	119.6
C7—C6—H6	119.7	C17—C18—C19	119.67 (19)
C8—C7—C6	120.27 (17)	C17—C18—H18	120.2
C8—C7—H7	119.9	C19—C18—H18	120.2
C6—C7—H7	119.9	C18—C19—C20	120.95 (18)
C9—C8—C7	119.51 (17)	C18—C19—H19	119.5
C9—C8—H8	120.2	C20—C19—H19	119.5
C7—C8—H8	120.2	C19—C20—C3	119.77 (19)
C8—C9—C10	120.57 (17)	C19—C20—H20	120.1
C8—C9—H9	119.7	C3—C20—H20	120.1
C10—C9—H9	119.7	C1—N1—C11	119.46 (13)
C9—C10—C5	120.50 (16)	C1—N1—C4	122.85 (13)
C9—C10—H10	119.8	C11—N1—C4	117.68 (12)
C5—C10—H10	119.8	C3—S1—C4	95.64 (7)
C12—C11—C16	119.43 (16)
O1—C1—C2—C17	18.8 (2)	N1—C11—C16—C15	−178.59 (18)
N1—C1—C2—C17	−161.54 (14)	C14—C15—C16—C11	−0.6 (3)
O1—C1—C2—C3	−157.41 (17)	C3—C2—C17—C18	0.1 (3)
N1—C1—C2—C3	22.2 (2)	C1—C2—C17—C18	−176.35 (16)
C17—C2—C3—C20	−0.9 (2)	C2—C17—C18—C19	0.9 (3)
C1—C2—C3—C20	175.31 (15)	C17—C18—C19—C20	−1.0 (3)
C17—C2—C3—S1	−178.93 (12)	C18—C19—C20—C3	0.2 (3)
C1—C2—C3—S1	−2.7 (2)	C2—C3—C20—C19	0.8 (3)
N1—C4—C5—C6	−1.3 (2)	S1—C3—C20—C19	178.82 (14)
S1—C4—C5—C6	124.86 (14)	O1—C1—N1—C11	9.4 (2)
N1—C4—C5—C10	175.80 (13)	C2—C1—N1—C11	−170.25 (13)
S1—C4—C5—C10	−58.01 (16)	O1—C1—N1—C4	−171.62 (16)
C10—C5—C6—C7	0.6 (2)	C2—C1—N1—C4	8.8 (2)
C4—C5—C6—C7	177.72 (15)	C12—C11—N1—C1	−114.62 (19)
C5—C6—C7—C8	−0.7 (3)	C16—C11—N1—C1	66.1 (2)
C6—C7—C8—C9	0.0 (3)	C12—C11—N1—C4	66.3 (2)
C7—C8—C9—C10	0.7 (3)	C16—C11—N1—C4	−113.00 (18)
C8—C9—C10—C5	−0.7 (3)	C5—C4—N1—C1	75.41 (18)
C6—C5—C10—C9	0.1 (2)	S1—C4—N1—C1	−51.67 (17)
C4—C5—C10—C9	−177.16 (14)	C5—C4—N1—C11	−105.55 (15)
C16—C11—C12—C13	−1.6 (3)	S1—C4—N1—C11	127.37 (12)
N1—C11—C12—C13	179.11 (19)	C20—C3—S1—C4	148.70 (14)
C11—C12—C13—C14	−0.4 (4)	C2—C3—S1—C4	−33.26 (15)
C12—C13—C14—C15	1.8 (4)	N1—C4—S1—C3	56.83 (12)
C13—C14—C15—C16	−1.3 (3)	C5—C4—S1—C3	−72.06 (12)
C12—C11—C16—C15	2.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1i	0.93	2.82	3.422 (2)	124
C15—H15···O1ii	0.93	2.69	3.477 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1i	0.93	2.82	3.422 (2)	124
C15—H15⋯O1ii	0.93	2.69	3.477 (2)	142

Symmetry codes: (i) ; (ii) .