3-[(Z)-Benzyl-idene]-2,3-dihydro-1,5-benzothia-zepin-4(5H)-one.

In the title compound, C(16)H(13)NOS, the seven-membered ring adopts a distorted half-chair conformation. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains running along the b axis. The crystal packing is further stabilized by C-H⋯O inter-actions.

Related literature

For the pharmaceutical properties of thia­zepin derivatives, see: Tomascovic et al. (2000 ▶); Rajsner et al. (1971 ▶); Metys et al. (1965 ▶). For the conformation of thia­zepin derivatives, see: Sridevi et al. (2011 ▶).

Experimental

Crystal data

C16H13NOS

M = 267.33

Orthorhombic,

a = 10.7711 (9) Å

b = 7.8736 (7) Å

c = 31.610 (3) Å

V = 2680.7 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.2 × 0.2 × 0.2 mm

Data collection

Bruker KappaCCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.980, T max = 0.990

13085 measured reflections

3306 independent reflections

2643 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.04

3306 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042991/bt5678sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042991/bt5678Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042991/bt5678Isup3.cml

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

C16H13NOS	F(000) = 1120
Mr = 267.33	Dx = 1.325 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8725 reflections
a = 10.7711 (9) Å	θ = 2.8–29.1°
b = 7.8736 (7) Å	µ = 0.23 mm−1
c = 31.610 (3) Å	T = 293 K
V = 2680.7 (4) Å3	Orthorhombic, colourless
Z = 8	0.2 × 0.2 × 0.2 mm

Bruker KappaCCD APEXII diffractometer	3306 independent reflections
Radiation source: fine-focus sealed tube	2643 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 15.9948 pixels mm-1	θmax = 28.3°, θmin = 1.3°
ω scans	h = −14→7
Absorption correction: multi-scan (APEX2; Bruker, 2004)	k = −5→10
Tmin = 0.980, Tmax = 0.990	l = −23→42
13085 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.6524P] where P = (Fo2 + 2Fc2)/3
3306 reflections	(Δ/σ)max = 0.002
180 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.22 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
H10	1.0606 (16)	−0.099 (2)	0.6162 (5)	0.048 (5)*
H	0.8379 (16)	0.440 (2)	0.6294 (5)	0.042 (4)*
S	0.90221 (4)	0.20135 (6)	0.529568 (12)	0.04764 (14)
O	0.73812 (10)	0.16660 (13)	0.64118 (3)	0.0435 (3)
N	0.88207 (11)	0.35628 (15)	0.61960 (4)	0.0351 (3)
C8	0.90106 (16)	0.01129 (19)	0.56317 (5)	0.0461 (4)
H8A	0.8216	−0.0458	0.5605	0.055*
H8B	0.9653	−0.0665	0.5538	0.055*
C7	0.92280 (14)	0.05759 (17)	0.60855 (4)	0.0359 (3)
C6	0.83940 (13)	0.19642 (17)	0.62461 (4)	0.0333 (3)
C1	1.11685 (15)	0.3856 (2)	0.53349 (5)	0.0445 (4)
H1	1.1331	0.3404	0.5069	0.053*
C5	0.98953 (13)	0.39991 (16)	0.59611 (4)	0.0332 (3)
C2	1.19757 (16)	0.5031 (2)	0.55064 (6)	0.0494 (4)
H2	1.2669	0.5381	0.5354	0.059*
C4	1.07215 (15)	0.51731 (19)	0.61325 (5)	0.0432 (4)
H4	1.0580	0.5614	0.6401	0.052*
C9	1.01129 (14)	0.33387 (17)	0.55554 (4)	0.0359 (3)
C16	0.98687 (17)	0.1038 (2)	0.70536 (5)	0.0515 (4)
H16	0.9123	0.1553	0.6980	0.062*
C11	1.05193 (15)	0.01041 (19)	0.67530 (5)	0.0412 (3)
C3	1.17543 (16)	0.5686 (2)	0.59035 (6)	0.0494 (4)
H3	1.2300	0.6476	0.6019	0.059*
C13	1.2089 (2)	−0.0450 (3)	0.72861 (7)	0.0690 (6)
H13	1.2840	−0.0947	0.7362	0.083*
C14	1.1430 (2)	0.0472 (3)	0.75774 (7)	0.0667 (6)
H14	1.1730	0.0599	0.7851	0.080*
C10	1.01213 (15)	−0.01630 (18)	0.63123 (5)	0.0400 (3)
C12	1.16375 (17)	−0.0644 (2)	0.68770 (6)	0.0555 (4)
H12	1.2087	−0.1283	0.6683	0.067*
C15	1.0318 (2)	0.1210 (3)	0.74614 (6)	0.0626 (5)
H15	0.9867	0.1830	0.7659	0.075*

	U11	U22	U33	U12	U13	U23
S	0.0540 (3)	0.0560 (3)	0.0329 (2)	−0.00587 (19)	−0.00722 (17)	−0.00413 (17)
O	0.0376 (6)	0.0446 (6)	0.0483 (6)	−0.0052 (5)	0.0072 (5)	−0.0052 (5)
N	0.0361 (7)	0.0308 (6)	0.0385 (6)	0.0026 (5)	0.0060 (5)	−0.0043 (5)
C8	0.0582 (10)	0.0399 (8)	0.0403 (8)	−0.0077 (7)	0.0035 (7)	−0.0108 (6)
C7	0.0417 (8)	0.0298 (6)	0.0361 (7)	−0.0036 (6)	0.0064 (6)	−0.0030 (5)
C6	0.0345 (7)	0.0355 (7)	0.0299 (6)	−0.0014 (6)	−0.0017 (5)	−0.0031 (5)
C1	0.0500 (9)	0.0433 (8)	0.0401 (8)	0.0036 (7)	0.0095 (7)	0.0038 (7)
C5	0.0341 (7)	0.0283 (6)	0.0372 (7)	0.0031 (5)	0.0010 (6)	0.0020 (5)
C2	0.0441 (9)	0.0434 (8)	0.0607 (10)	−0.0010 (7)	0.0135 (8)	0.0078 (7)
C4	0.0464 (9)	0.0358 (7)	0.0472 (9)	−0.0032 (7)	0.0022 (7)	−0.0056 (6)
C9	0.0388 (8)	0.0343 (7)	0.0345 (7)	0.0022 (6)	−0.0006 (6)	0.0018 (5)
C16	0.0490 (10)	0.0629 (10)	0.0425 (9)	0.0091 (8)	−0.0011 (7)	−0.0004 (8)
C11	0.0413 (8)	0.0367 (7)	0.0457 (8)	0.0010 (6)	0.0020 (7)	0.0063 (6)
C3	0.0447 (9)	0.0383 (8)	0.0652 (11)	−0.0079 (7)	0.0023 (8)	−0.0021 (7)
C13	0.0549 (11)	0.0700 (13)	0.0821 (14)	0.0031 (10)	−0.0195 (10)	0.0156 (11)
C14	0.0707 (13)	0.0733 (13)	0.0561 (11)	−0.0123 (11)	−0.0206 (10)	0.0097 (10)
C10	0.0448 (9)	0.0311 (7)	0.0442 (8)	0.0034 (6)	0.0101 (7)	−0.0017 (6)
C12	0.0491 (10)	0.0524 (10)	0.0649 (11)	0.0090 (8)	0.0010 (8)	0.0075 (8)
C15	0.0678 (13)	0.0746 (12)	0.0454 (9)	0.0002 (10)	−0.0033 (9)	−0.0049 (9)

S—C9	1.7728 (15)	C2—H2	0.9300
S—C8	1.8352 (17)	C4—C3	1.387 (2)
O—C6	1.2326 (17)	C4—H4	0.9300
N—C6	1.3493 (18)	C16—C15	1.384 (2)
N—C5	1.4174 (18)	C16—C11	1.391 (2)
N—H	0.872 (18)	C16—H16	0.9300
C8—C7	1.498 (2)	C11—C12	1.397 (2)
C8—H8A	0.9700	C11—C10	1.473 (2)
C8—H8B	0.9700	C3—H3	0.9300
C7—C10	1.334 (2)	C13—C14	1.371 (3)
C7—C6	1.503 (2)	C13—C12	1.390 (3)
C6—O	1.2326 (17)	C13—H13	0.9300
C1—C2	1.381 (2)	C14—C15	1.381 (3)
C1—C9	1.394 (2)	C14—H14	0.9300
C1—H1	0.9300	C10—H10	0.962 (18)
C5—C4	1.393 (2)	C12—H12	0.9300
C5—C9	1.4037 (19)	C15—H15	0.9300
C2—C3	1.378 (2)
C9—S—C8	102.50 (7)	C5—C4—H4	119.9
C6—N—C5	124.46 (12)	C1—C9—C5	118.98 (14)
C6—N—H	118.7 (11)	C1—C9—S	118.75 (12)
C5—N—H	116.6 (11)	C5—C9—S	122.04 (11)
C7—C8—S	110.78 (10)	C15—C16—C11	120.80 (17)
C7—C8—H8A	109.5	C15—C16—H16	119.6
S—C8—H8A	109.5	C11—C16—H16	119.6
C7—C8—H8B	109.5	C16—C11—C12	117.75 (16)
S—C8—H8B	109.5	C16—C11—C10	125.11 (15)
H8A—C8—H8B	108.1	C12—C11—C10	117.14 (15)
C10—C7—C8	121.42 (14)	C2—C3—C4	120.34 (16)
C10—C7—C6	124.53 (13)	C2—C3—H3	119.8
C8—C7—C6	114.01 (13)	C4—C3—H3	119.8
O—C6—N	121.94 (13)	C14—C13—C12	120.12 (19)
O—C6—N	121.94 (13)	C14—C13—H13	119.9
O—C6—C7	122.26 (13)	C12—C13—H13	119.9
O—C6—C7	122.26 (13)	C13—C14—C15	119.60 (19)
N—C6—C7	115.79 (12)	C13—C14—H14	120.2
C2—C1—C9	120.89 (15)	C15—C14—H14	120.2
C2—C1—H1	119.6	C7—C10—C11	131.02 (14)
C9—C1—H1	119.6	C7—C10—H10	115.1 (11)
C4—C5—C9	119.65 (13)	C11—C10—H10	113.9 (11)
C4—C5—N	118.61 (13)	C13—C12—C11	121.10 (18)
C9—C5—N	121.68 (13)	C13—C12—H12	119.5
C3—C2—C1	119.96 (15)	C11—C12—H12	119.5
C3—C2—H2	120.0	C14—C15—C16	120.63 (19)
C1—C2—H2	120.0	C14—C15—H15	119.7
C3—C4—C5	120.17 (15)	C16—C15—H15	119.7
C3—C4—H4	119.9
C9—S—C8—C7	32.87 (13)	C4—C5—C9—C1	1.0 (2)
S—C8—C7—C10	−126.73 (14)	N—C5—C9—C1	178.07 (13)
S—C8—C7—C6	50.98 (16)	C4—C5—C9—S	−173.34 (11)
O—O—C6—N	0.0 (4)	N—C5—C9—S	3.70 (19)
O—O—C6—C7	0.0 (3)	C8—S—C9—C1	120.08 (13)
C5—N—C6—O	−171.54 (13)	C8—S—C9—C5	−65.54 (13)
C5—N—C6—O	−171.54 (13)	C15—C16—C11—C12	−0.2 (3)
C5—N—C6—C7	8.2 (2)	C15—C16—C11—C10	179.74 (17)
C10—C7—C6—O	−92.01 (19)	C1—C2—C3—C4	−0.1 (3)
C8—C7—C6—O	90.37 (16)	C5—C4—C3—C2	−0.4 (3)
C10—C7—C6—O	−92.01 (19)	C12—C13—C14—C15	−0.2 (3)
C8—C7—C6—O	90.37 (16)	C8—C7—C10—C11	178.60 (15)
C10—C7—C6—N	88.27 (18)	C6—C7—C10—C11	1.1 (3)
C8—C7—C6—N	−89.35 (16)	C16—C11—C10—C7	11.7 (3)
C6—N—C5—C4	−135.93 (15)	C12—C11—C10—C7	−168.36 (17)
C6—N—C5—C9	47.0 (2)	C14—C13—C12—C11	0.7 (3)
C9—C1—C2—C3	1.1 (2)	C16—C11—C12—C13	−0.5 (3)
C9—C5—C4—C3	0.0 (2)	C10—C11—C12—C13	179.57 (17)
N—C5—C4—C3	−177.16 (14)	C13—C14—C15—C16	−0.4 (3)
C2—C1—C9—C5	−1.6 (2)	C11—C16—C15—C14	0.6 (3)
C2—C1—C9—S	172.96 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N—H···Oi	0.872 (18)	1.996 (18)	2.8480 (16)	165.4 (16)
C14—H14···Oii	0.93	2.57	3.485 (2)	167.
C16—H16···O	0.93	2.60	3.397 (2)	144.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H⋯Oi	0.872 (18)	1.996 (18)	2.8480 (16)	165.4 (16)
C14—H14⋯Oii	0.93	2.57	3.485 (2)	167
C16—H16⋯O	0.93	2.60	3.397 (2)	144

Symmetry codes: (i) ; (ii) .