3-(2-Methyl-benzyl-idene)-2,3-dihydro-1,5-benzothia-zepin-4(5H)-one.

In the crystal structure of the title compound, C(17)H(15)NOS, the mol-ecules form centrosymmetric dimers through pairs of N-H⋯O hydrogen bonds. The seven-membered ring adopts a distorted half-chair conformation.

Related literature

Dibenzo[c,e]thiepine derivatives exhibit chiroptical properties (Tomascovic et al., 2000 ▶) and dibenzo[b,e]thiepin-5,5-dioxide derivatives possess anti­histaminic and anti­allergenic activities (Rajsner et al., 1971 ▶) while benzene thiepine derivatives have been identified as effective anti­histaminic compounds (Metys et al., 1965 ▶).

Experimental

Crystal data

C17H15NOS

M = 281.36

Monoclinic,

a = 19.1192 (5) Å

b = 13.0049 (3) Å

c = 14.8903 (4) Å

β = 128.591 (1)°

V = 2893.84 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.22 × 0.18 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

13879 measured reflections

3560 independent reflections

2707 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.202

S = 0.83

3560 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052888/bt5422sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052888/bt5422Isup2.hkl

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

C17H15NOS	F(000) = 1184
Mr = 281.36	Dx = 1.292 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.1192 (5) Å	Cell parameters from 3560 reflections
b = 13.0049 (3) Å	θ = 2–28°
c = 14.8903 (4) Å	µ = 0.22 mm−1
β = 128.591 (1)°	T = 293 K
V = 2893.84 (13) Å3	Block, colourless
Z = 8	0.22 × 0.18 × 0.18 mm

Bruker Kappa APEXII CCD diffractometer	2707 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 28.4°, θmin = 2.1°
ω and φ scans	h = −25→20
13879 measured reflections	k = −15→16
3560 independent reflections	l = −15→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202	H-atom parameters constrained
S = 0.83	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
3560 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.30 e Å−3
0 constraints

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	0.07250 (13)	0.88179 (15)	0.21097 (16)	0.0540 (5)
H1	0.1146	0.9233	0.2730	0.065*
C2	−0.00643 (15)	0.92462 (17)	0.11794 (18)	0.0623 (5)
H2	−0.0169	0.9947	0.1164	0.075*
C3	−0.06956 (12)	0.86298 (15)	0.02748 (16)	0.0557 (5)
H3	−0.1233	0.8912	−0.0351	0.067*
C4	−0.05362 (11)	0.75966 (14)	0.02896 (14)	0.0448 (4)
H4	−0.0970	0.7185	−0.0326	0.054*
C5	0.02685 (10)	0.71567 (12)	0.12171 (12)	0.0365 (4)
C6	0.08537 (12)	0.52859 (14)	0.17690 (13)	0.0485 (4)
C7	0.14280 (11)	0.52918 (13)	0.30555 (12)	0.0424 (4)
C8	0.15581 (12)	0.62540 (13)	0.36935 (13)	0.0478 (4)
H8A	0.1988	0.6123	0.4512	0.057*
H8B	0.0995	0.6441	0.3523	0.057*
C9	0.09042 (10)	0.77806 (13)	0.21391 (13)	0.0398 (4)
C10	0.18328 (12)	0.44083 (13)	0.35720 (14)	0.0477 (4)
H10	0.1742	0.3876	0.3092	0.057*
C11	0.24053 (11)	0.41648 (13)	0.48045 (14)	0.0449 (4)
C12	0.21413 (14)	0.43985 (16)	0.54648 (16)	0.0573 (5)
H12	0.1612	0.4759	0.5135	0.069*
C13	0.26536 (17)	0.4103 (2)	0.66057 (18)	0.0723 (7)
H13	0.2472	0.4269	0.7040	0.087*
C14	0.34253 (16)	0.35663 (19)	0.70886 (18)	0.0750 (7)
H14	0.3770	0.3360	0.7853	0.090*
C15	0.36932 (13)	0.33310 (17)	0.64501 (18)	0.0676 (6)
H15	0.4222	0.2966	0.6792	0.081*
C16	0.31970 (11)	0.36225 (14)	0.52991 (15)	0.0504 (4)
C17	0.35129 (16)	0.33506 (19)	0.4639 (2)	0.0722 (6)
H17A	0.4068	0.2983	0.5126	0.108*
H17B	0.3601	0.3967	0.4366	0.108*
H17C	0.3074	0.2926	0.3997	0.108*
N	0.03793 (9)	0.61072 (12)	0.10949 (10)	0.0450 (4)
H0	0.0047	0.5939	0.0381	0.054*
O	0.07844 (12)	0.44836 (11)	0.12814 (11)	0.0766 (5)
S1	0.19459 (3)	0.73150 (4)	0.33323 (3)	0.0503 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0582 (10)	0.0419 (10)	0.0457 (9)	−0.0007 (8)	0.0246 (8)	−0.0069 (7)
C2	0.0737 (12)	0.0426 (10)	0.0558 (11)	0.0134 (8)	0.0332 (10)	0.0055 (8)
C3	0.0507 (9)	0.0560 (12)	0.0456 (10)	0.0109 (8)	0.0228 (8)	0.0110 (8)
C4	0.0400 (8)	0.0503 (10)	0.0332 (8)	−0.0013 (6)	0.0174 (7)	0.0027 (6)
C5	0.0373 (7)	0.0405 (8)	0.0284 (7)	−0.0002 (6)	0.0190 (6)	0.0005 (6)
C6	0.0570 (9)	0.0436 (10)	0.0281 (7)	0.0032 (7)	0.0183 (7)	−0.0047 (6)
C7	0.0501 (8)	0.0414 (9)	0.0262 (7)	0.0001 (7)	0.0192 (6)	−0.0041 (6)
C8	0.0600 (9)	0.0448 (10)	0.0258 (7)	0.0080 (7)	0.0205 (7)	−0.0024 (6)
C9	0.0391 (7)	0.0424 (9)	0.0305 (7)	0.0003 (6)	0.0180 (6)	0.0004 (6)
C10	0.0579 (9)	0.0426 (10)	0.0323 (8)	−0.0020 (7)	0.0231 (8)	−0.0030 (7)
C11	0.0497 (8)	0.0391 (9)	0.0345 (8)	−0.0061 (6)	0.0207 (7)	0.0027 (6)
C12	0.0610 (10)	0.0628 (13)	0.0444 (10)	−0.0029 (9)	0.0310 (9)	0.0050 (8)
C13	0.0867 (16)	0.0852 (17)	0.0483 (11)	−0.0180 (12)	0.0438 (12)	0.0024 (11)
C14	0.0811 (14)	0.0757 (16)	0.0366 (9)	−0.0188 (12)	0.0211 (10)	0.0107 (9)
C15	0.0500 (9)	0.0583 (13)	0.0547 (12)	−0.0067 (8)	0.0131 (9)	0.0079 (9)
C16	0.0489 (8)	0.0429 (10)	0.0442 (9)	−0.0116 (7)	0.0217 (8)	−0.0030 (7)
C17	0.0664 (12)	0.0654 (14)	0.0809 (16)	−0.0040 (10)	0.0441 (12)	−0.0149 (11)
N	0.0499 (7)	0.0433 (8)	0.0229 (6)	0.0019 (6)	0.0135 (6)	−0.0046 (5)
O	0.1042 (12)	0.0492 (9)	0.0302 (6)	0.0191 (8)	0.0193 (7)	−0.0072 (5)
S1	0.0394 (3)	0.0464 (3)	0.0371 (3)	−0.00100 (15)	0.0101 (2)	−0.00664 (16)

C1—C2	1.378 (3)	C9—S1	1.7538 (16)
C1—C9	1.386 (2)	C10—C11	1.470 (2)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.373 (3)	C11—C16	1.393 (3)
C2—H2	0.9300	C11—C12	1.390 (3)
C3—C4	1.375 (3)	C12—C13	1.385 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.397 (2)	C13—C14	1.363 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C9	1.392 (2)	C14—C15	1.367 (4)
C5—N	1.410 (2)	C14—H14	0.9300
C6—O	1.230 (2)	C15—C16	1.397 (3)
C6—N	1.355 (2)	C15—H15	0.9300
C6—C7	1.501 (2)	C16—C17	1.482 (3)
C7—C10	1.330 (2)	C17—H17A	0.9600
C7—C8	1.495 (2)	C17—H17B	0.9600
C8—S1	1.8001 (19)	C17—H17C	0.9600
C8—H8A	0.9700	N—H0	0.8600
C8—H8B	0.9700
C2—C1—C9	121.29 (17)	C7—C10—H10	115.8
C2—C1—H1	119.4	C11—C10—H10	115.8
C9—C1—H1	119.4	C16—C11—C12	119.40 (16)
C3—C2—C1	119.44 (19)	C16—C11—C10	119.11 (17)
C3—C2—H2	120.3	C12—C11—C10	121.33 (17)
C1—C2—H2	120.3	C13—C12—C11	121.1 (2)
C2—C3—C4	120.29 (17)	C13—C12—H12	119.5
C2—C3—H3	119.9	C11—C12—H12	119.5
C4—C3—H3	119.9	C14—C13—C12	119.6 (2)
C3—C4—C5	120.83 (16)	C14—C13—H13	120.2
C3—C4—H4	119.6	C12—C13—H13	120.2
C5—C4—H4	119.6	C15—C14—C13	119.99 (19)
C9—C5—C4	118.81 (15)	C15—C14—H14	120.0
C9—C5—N	125.61 (14)	C13—C14—H14	120.0
C4—C5—N	115.48 (14)	C14—C15—C16	122.0 (2)
O—C6—N	117.10 (14)	C14—C15—H15	119.0
O—C6—C7	118.78 (15)	C16—C15—H15	119.0
N—C6—C7	124.09 (14)	C11—C16—C15	117.93 (19)
C10—C7—C8	123.34 (14)	C11—C16—C17	121.88 (18)
C10—C7—C6	115.63 (14)	C15—C16—C17	120.2 (2)
C8—C7—C6	120.97 (14)	C16—C17—H17A	109.5
C7—C8—S1	112.83 (12)	C16—C17—H17B	109.5
C7—C8—H8A	109.0	H17A—C17—H17B	109.5
S1—C8—H8A	109.0	C16—C17—H17C	109.5
C7—C8—H8B	109.0	H17A—C17—H17C	109.5
S1—C8—H8B	109.0	H17B—C17—H17C	109.5
H8A—C8—H8B	107.8	C6—N—C5	138.81 (13)
C1—C9—C5	119.31 (15)	C6—N—H0	110.6
C1—C9—S1	118.05 (13)	C5—N—H0	110.6
C5—C9—S1	122.61 (13)	C9—S1—C8	98.53 (8)
C7—C10—C11	128.30 (16)
C9—C1—C2—C3	1.6 (3)	C7—C10—C11—C12	49.1 (3)
C1—C2—C3—C4	−0.9 (3)	C16—C11—C12—C13	0.1 (3)
C2—C3—C4—C5	−0.3 (3)	C10—C11—C12—C13	175.39 (19)
C3—C4—C5—C9	1.0 (2)	C11—C12—C13—C14	−0.6 (3)
C3—C4—C5—N	−175.59 (16)	C12—C13—C14—C15	0.5 (4)
O—C6—C7—C10	0.9 (3)	C13—C14—C15—C16	−0.1 (3)
N—C6—C7—C10	178.94 (17)	C12—C11—C16—C15	0.3 (3)
O—C6—C7—C8	178.10 (19)	C10—C11—C16—C15	−175.08 (17)
N—C6—C7—C8	−3.8 (3)	C12—C11—C16—C17	179.97 (18)
C10—C7—C8—S1	123.26 (16)	C10—C11—C16—C17	4.6 (3)
C6—C7—C8—S1	−53.7 (2)	C14—C15—C16—C11	−0.3 (3)
C2—C1—C9—C5	−0.9 (3)	C14—C15—C16—C17	−180.0 (2)
C2—C1—C9—S1	177.38 (15)	O—C6—N—C5	−175.66 (19)
C4—C5—C9—C1	−0.4 (2)	C7—C6—N—C5	6.3 (3)
N—C5—C9—C1	175.84 (16)	C9—C5—N—C6	26.7 (3)
C4—C5—C9—S1	−178.59 (12)	C4—C5—N—C6	−157.0 (2)
N—C5—C9—S1	−2.4 (2)	C1—C9—S1—C8	128.73 (15)
C8—C7—C10—C11	5.3 (3)	C5—C9—S1—C8	−53.03 (15)
C6—C7—C10—C11	−177.56 (18)	C7—C8—S1—C9	87.11 (13)
C7—C10—C11—C16	−135.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0···Oi	0.86	2.01	2.8705 (18)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0⋯Oi	0.86	2.01	2.8705 (18)	177

Symmetry code: (i) .