(Z)-3-(4-Chloro-benz-yl)-1,5-benzothia-zepin-4(5H)-one.

In the title compound, C(16)H(12)ClNOS, the seven-membered thia-zepine ring adopts a distorted twisted boat conformation. The dihedral angle between the least-squares planes of the 1,5-benzothia-zepine ring system and the benzene ring is 50.2 (1)°. In the crystal, pairs of N-H⋯O hydrogen bonds link centrosymmetrically related mol-ecules into dimers, generating R(2) (2)(8) ring motifs. The crystal packing is further stabilized by π-π inter-actions [centroid-centroid distance = 3.763 (2) Å].

Related literature

For the pharmaceutical properties of thia­zepin derivatives, see: Tomascovic et al. (2000 ▶); Rajsner et al. (1971 ▶); Metys et al. (1965 ▶). For related structures, see: Sridevi et al. (2011 ▶); Sabari et al. (2011 ▶); Selvakumar et al. (2012 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H12ClNOS

M = 301.78

Orthorhombic,

a = 9.0486 (3) Å

b = 9.4105 (3) Å

c = 33.4876 (10) Å

V = 2851.53 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.23 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.910, T max = 0.941

14850 measured reflections

3099 independent reflections

2382 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.118

S = 1.03

3099 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026608/tk5111sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026608/tk5111Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026608/tk5111Isup3.cml

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

C16H12ClNOS	F(000) = 1248
Mr = 301.78	Dx = 1.406 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3130 reflections
a = 9.0486 (3) Å	θ = 2.4–27.0°
b = 9.4105 (3) Å	µ = 0.41 mm−1
c = 33.4876 (10) Å	T = 293 K
V = 2851.53 (16) Å3	Block, colourless
Z = 8	0.23 × 0.21 × 0.15 mm

Bruker APEXII CCD diffractometer	3099 independent reflections
Radiation source: fine-focus sealed tube	2382 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.4°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→11
Tmin = 0.910, Tmax = 0.941	l = −42→29
14850 measured 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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0432P)2 + 1.9074P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3099 reflections	Δρmax = 0.35 e Å−3
182 parameters	Δρmin = −0.45 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (6)

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	0.0719 (3)	0.1514 (2)	0.12513 (6)	0.0476 (5)
H1A	0.0655	0.1466	0.1528	0.057*
C2	0.0392 (2)	0.3707 (2)	0.07497 (6)	0.0435 (5)
C3	0.0021 (3)	0.5128 (3)	0.08041 (7)	0.0580 (7)
H3	0.0457	0.5643	0.1010	0.070*
C4	−0.0985 (3)	0.5777 (3)	0.05567 (8)	0.0618 (7)
H4	−0.1210	0.6733	0.0592	0.074*
C5	−0.1654 (3)	0.5023 (2)	0.02586 (8)	0.0518 (6)
H5	−0.2335	0.5466	0.0092	0.062*
C6	−0.1323 (2)	0.3610 (2)	0.02049 (7)	0.0434 (5)
H6	−0.1789	0.3098	0.0004	0.052*
C7	−0.0300 (2)	0.2947 (2)	0.04485 (6)	0.0373 (4)
C8	0.0158 (2)	0.0388 (2)	0.06027 (6)	0.0399 (5)
C9	0.0015 (2)	0.0533 (2)	0.10436 (6)	0.0416 (5)
C10	−0.0895 (3)	−0.0641 (3)	0.12279 (7)	0.0555 (6)
H10A	−0.1879	−0.0612	0.1114	0.067*
H10B	−0.0457	−0.1547	0.1156	0.067*
C11	−0.1027 (3)	−0.0572 (2)	0.16758 (7)	0.0489 (6)
C12	−0.0147 (3)	−0.1404 (3)	0.19132 (8)	0.0590 (6)
H12	0.0524	−0.2022	0.1794	0.071*
C13	−0.0233 (3)	−0.1346 (3)	0.23246 (8)	0.0668 (7)
H13	0.0367	−0.1922	0.2482	0.080*
C14	−0.1208 (3)	−0.0436 (3)	0.24963 (8)	0.0639 (7)
C15	−0.2101 (3)	0.0408 (3)	0.22704 (9)	0.0733 (8)
H15	−0.2766	0.1028	0.2391	0.088*
C16	−0.2004 (3)	0.0329 (3)	0.18587 (8)	0.0664 (7)
H16	−0.2614	0.0899	0.1703	0.080*
N1	0.0078 (2)	0.15261 (18)	0.03612 (5)	0.0405 (4)
H1	0.0290	0.1363	0.0115	0.049*
O1	0.0322 (2)	−0.08062 (16)	0.04596 (4)	0.0551 (4)
S1	0.17684 (7)	0.29044 (7)	0.104528 (18)	0.0568 (2)
Cl1	−0.13112 (12)	−0.03656 (12)	0.30146 (2)	0.1046 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0518 (13)	0.0530 (13)	0.0379 (11)	−0.0069 (11)	−0.0027 (10)	0.0015 (10)
C2	0.0495 (13)	0.0381 (12)	0.0428 (11)	−0.0122 (10)	0.0066 (9)	−0.0021 (9)
C3	0.0789 (18)	0.0400 (13)	0.0552 (14)	−0.0191 (13)	0.0111 (13)	−0.0109 (11)
C4	0.0796 (19)	0.0336 (12)	0.0721 (17)	0.0004 (12)	0.0225 (15)	−0.0012 (12)
C5	0.0508 (14)	0.0379 (12)	0.0667 (15)	0.0020 (11)	0.0135 (12)	0.0109 (11)
C6	0.0418 (11)	0.0363 (12)	0.0522 (12)	−0.0045 (9)	0.0039 (10)	0.0036 (9)
C7	0.0389 (11)	0.0328 (10)	0.0400 (10)	−0.0049 (9)	0.0067 (8)	−0.0009 (8)
C8	0.0440 (12)	0.0361 (12)	0.0396 (10)	0.0032 (9)	−0.0035 (9)	−0.0018 (9)
C9	0.0469 (12)	0.0398 (12)	0.0380 (10)	0.0010 (10)	−0.0028 (9)	0.0018 (9)
C10	0.0696 (16)	0.0478 (13)	0.0492 (13)	−0.0110 (12)	−0.0046 (12)	0.0040 (11)
C11	0.0515 (14)	0.0455 (13)	0.0497 (12)	−0.0084 (11)	−0.0005 (10)	0.0095 (10)
C12	0.0615 (16)	0.0559 (15)	0.0595 (14)	0.0044 (13)	−0.0010 (12)	0.0090 (12)
C13	0.0687 (18)	0.0723 (18)	0.0593 (15)	−0.0046 (15)	−0.0117 (14)	0.0210 (14)
C14	0.0653 (17)	0.0791 (18)	0.0472 (13)	−0.0228 (15)	0.0080 (12)	0.0081 (13)
C15	0.0719 (19)	0.078 (2)	0.0698 (17)	0.0061 (16)	0.0219 (15)	0.0040 (15)
C16	0.0631 (17)	0.0714 (18)	0.0645 (16)	0.0115 (14)	0.0025 (13)	0.0179 (14)
N1	0.0527 (11)	0.0347 (9)	0.0342 (8)	0.0024 (8)	0.0011 (8)	−0.0025 (7)
O1	0.0836 (12)	0.0365 (8)	0.0453 (8)	0.0120 (8)	−0.0058 (8)	−0.0030 (7)
S1	0.0541 (4)	0.0654 (4)	0.0509 (3)	−0.0224 (3)	−0.0093 (3)	0.0030 (3)
Cl1	0.1122 (7)	0.1522 (9)	0.0494 (4)	−0.0371 (7)	0.0121 (4)	0.0051 (5)

C1—C9	1.320 (3)	C8—C9	1.488 (3)
C1—S1	1.758 (2)	C9—C10	1.509 (3)
C1—H1A	0.9300	C10—C11	1.506 (3)
C2—C7	1.386 (3)	C10—H10A	0.9700
C2—C3	1.391 (3)	C10—H10B	0.9700
C2—S1	1.761 (2)	C11—C16	1.370 (4)
C3—C4	1.374 (4)	C11—C12	1.371 (3)
C3—H3	0.9300	C12—C13	1.381 (4)
C4—C5	1.366 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.357 (4)
C5—C6	1.374 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.363 (4)
C6—C7	1.382 (3)	C14—Cl1	1.739 (3)
C6—H6	0.9300	C15—C16	1.383 (4)
C7—N1	1.411 (3)	C15—H15	0.9300
C8—O1	1.231 (2)	C16—H16	0.9300
C8—N1	1.344 (3)	N1—H1	0.8600
C9—C1—S1	125.10 (17)	C11—C10—H10A	108.6
C9—C1—H1A	117.5	C9—C10—H10A	108.6
S1—C1—H1A	117.5	C11—C10—H10B	108.6
C7—C2—C3	118.8 (2)	C9—C10—H10B	108.6
C7—C2—S1	120.49 (17)	H10A—C10—H10B	107.6
C3—C2—S1	120.64 (18)	C16—C11—C12	118.0 (2)
C4—C3—C2	120.6 (2)	C16—C11—C10	121.6 (2)
C4—C3—H3	119.7	C12—C11—C10	120.5 (2)
C2—C3—H3	119.7	C11—C12—C13	121.5 (3)
C5—C4—C3	120.2 (2)	C11—C12—H12	119.2
C5—C4—H4	119.9	C13—C12—H12	119.2
C3—C4—H4	119.9	C14—C13—C12	119.0 (3)
C4—C5—C6	120.1 (2)	C14—C13—H13	120.5
C4—C5—H5	120.0	C12—C13—H13	120.5
C6—C5—H5	120.0	C13—C14—C15	121.2 (3)
C5—C6—C7	120.4 (2)	C13—C14—Cl1	118.8 (2)
C5—C6—H6	119.8	C15—C14—Cl1	120.0 (2)
C7—C6—H6	119.8	C14—C15—C16	118.9 (3)
C6—C7—C2	119.92 (19)	C14—C15—H15	120.5
C6—C7—N1	117.91 (18)	C16—C15—H15	120.5
C2—C7—N1	122.02 (19)	C11—C16—C15	121.3 (3)
O1—C8—N1	119.98 (18)	C11—C16—H16	119.3
O1—C8—C9	118.70 (18)	C15—C16—H16	119.3
N1—C8—C9	121.31 (18)	C8—N1—C7	130.05 (17)
C1—C9—C8	123.0 (2)	C8—N1—H1	115.0
C1—C9—C10	124.05 (19)	C7—N1—H1	115.0
C8—C9—C10	112.71 (18)	C1—S1—C2	99.08 (10)
C11—C10—C9	114.76 (19)
C7—C2—C3—C4	−1.7 (3)	C9—C10—C11—C16	79.7 (3)
S1—C2—C3—C4	175.82 (19)	C9—C10—C11—C12	−99.3 (3)
C2—C3—C4—C5	1.3 (4)	C16—C11—C12—C13	0.1 (4)
C3—C4—C5—C6	0.0 (4)	C10—C11—C12—C13	179.1 (2)
C4—C5—C6—C7	−0.7 (3)	C11—C12—C13—C14	−0.4 (4)
C5—C6—C7—C2	0.2 (3)	C12—C13—C14—C15	0.4 (4)
C5—C6—C7—N1	−175.39 (19)	C12—C13—C14—Cl1	−179.9 (2)
C3—C2—C7—C6	1.0 (3)	C13—C14—C15—C16	0.0 (4)
S1—C2—C7—C6	−176.59 (15)	Cl1—C14—C15—C16	−179.7 (2)
C3—C2—C7—N1	176.41 (19)	C12—C11—C16—C15	0.3 (4)
S1—C2—C7—N1	−1.2 (3)	C10—C11—C16—C15	−178.7 (2)
S1—C1—C9—C8	6.9 (3)	C14—C15—C16—C11	−0.3 (4)
S1—C1—C9—C10	−179.25 (19)	O1—C8—N1—C7	170.5 (2)
O1—C8—C9—C1	135.4 (2)	C9—C8—N1—C7	−8.1 (3)
N1—C8—C9—C1	−46.0 (3)	C6—C7—N1—C8	−131.7 (2)
O1—C8—C9—C10	−39.0 (3)	C2—C7—N1—C8	52.8 (3)
N1—C8—C9—C10	139.5 (2)	C9—C1—S1—C2	58.0 (2)
C1—C9—C10—C11	3.5 (3)	C7—C2—S1—C1	−60.21 (19)
C8—C9—C10—C11	177.9 (2)	C3—C2—S1—C1	122.26 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.07	2.854 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.07	2.854 (2)	151

Symmetry code: (i) .