(Z)-3-(2-Chloro-benz-yl)-1,5-benzothia-zepin-4(5H)-one.

In the crystal structure of the title compound, C(16)H(12)ClNOS, the mol-ecules are linked into centrosymmetric R(2) (2)(8) dimers via pairs of N-H⋯O hydrogen bonds. The seven-membered ring adopts a boat conformation.

Related literature

For the pharmaceutical properties of thia­zepin derivatives, see: Tomascovic et al. (2000 ▶); Rajsner et al. (1971 ▶); Metys et al. (1965 ▶). For conformations of thia­zepin derivatives, see: Huang et al. (2011 ▶). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H12ClNOS

M = 301.78

Triclinic,

a = 8.4958 (3) Å

b = 8.7197 (3) Å

c = 10.0520 (3) Å

α = 101.930 (1)°

β = 95.179 (2)°

γ = 90.314 (2)°

V = 725.38 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 298 K

0.32 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.980, T max = 0.990

10314 measured reflections

3596 independent reflections

2961 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 0.93

3596 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029030/bt5944sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029030/bt5944Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029030/bt5944Isup3.cml

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

C16H12ClNOS	Z = 2
Mr = 301.78	F(000) = 312
Triclinic, P1	Dx = 1.382 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4958 (3) Å	Cell parameters from 8725 reflections
b = 8.7197 (3) Å	θ = 2.8–29.1°
c = 10.0520 (3) Å	µ = 0.40 mm−1
α = 101.930 (1)°	T = 298 K
β = 95.179 (2)°	Triclinic, colourless
γ = 90.314 (2)°	0.32 × 0.20 × 0.10 mm
V = 725.38 (4) Å3

Bruker APEXII CCD area-detector diffractometer	3596 independent reflections
Radiation source: fine-focus sealed tube	2961 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 15.9948 pixels mm-1	θmax = 28.6°, θmin = 2.1°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −11→10
Tmin = 0.980, Tmax = 0.990	l = −12→13
10314 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0686P)2 + 0.3987P] where P = (Fo2 + 2Fc2)/3
3596 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.54 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	0.3986 (3)	0.7811 (3)	0.4385 (2)	0.0611 (6)
H1	0.3329	0.7850	0.3602	0.073*
C2	0.5362 (3)	0.6996 (3)	0.4275 (3)	0.0727 (7)
H2	0.5640	0.6500	0.3421	0.087*
C3	0.6327 (3)	0.6915 (3)	0.5429 (3)	0.0686 (6)
H3	0.7259	0.6362	0.5354	0.082*
C4	0.5921 (2)	0.7650 (3)	0.6696 (2)	0.0554 (5)
H4	0.6578	0.7587	0.7474	0.066*
C5	0.45365 (19)	0.8482 (2)	0.68197 (17)	0.0400 (4)
N1	0.42278 (17)	0.92803 (19)	0.81405 (14)	0.0425 (3)
C6	0.29024 (18)	0.92977 (19)	0.87848 (16)	0.0352 (3)
C7	0.13755 (18)	0.85995 (19)	0.80480 (17)	0.0361 (3)
C8	0.0826 (2)	0.8806 (2)	0.68177 (19)	0.0455 (4)
H8	−0.0194	0.8430	0.6497	0.055*
C9	0.3563 (2)	0.8580 (2)	0.56553 (17)	0.0429 (4)
C10	0.0416 (2)	0.7741 (2)	0.88754 (19)	0.0435 (4)
H10A	0.0236	0.8440	0.9730	0.052*
H10B	−0.0604	0.7426	0.8376	0.052*
C11	0.12551 (19)	0.6308 (2)	0.91707 (17)	0.0382 (4)
C12	0.2153 (2)	0.6381 (2)	1.0410 (2)	0.0506 (4)
H12	0.2198	0.7312	1.1062	0.061*
C13	0.2978 (3)	0.5119 (3)	1.0702 (2)	0.0615 (6)
H13	0.3578	0.5212	1.1538	0.074*
C14	0.2922 (3)	0.3731 (3)	0.9772 (3)	0.0622 (6)
H14	0.3486	0.2882	0.9970	0.075*
C15	0.2030 (3)	0.3594 (3)	0.8545 (2)	0.0594 (5)
H15	0.1969	0.2646	0.7914	0.071*
C16	0.1220 (2)	0.4874 (2)	0.82485 (18)	0.0466 (4)
Cl1	0.01021 (9)	0.46470 (9)	0.66795 (6)	0.0789 (2)
O1	0.29428 (15)	0.98862 (16)	1.00167 (12)	0.0457 (3)
S1	0.18502 (6)	0.97237 (7)	0.57440 (5)	0.05265 (16)
H1A	0.501 (3)	0.958 (3)	0.867 (2)	0.051 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0598 (12)	0.0839 (16)	0.0365 (9)	−0.0198 (11)	−0.0013 (8)	0.0081 (9)
C2	0.0641 (14)	0.0927 (18)	0.0539 (13)	−0.0154 (13)	0.0192 (11)	−0.0075 (12)
C3	0.0482 (11)	0.0836 (17)	0.0714 (15)	0.0037 (11)	0.0188 (10)	0.0043 (12)
C4	0.0397 (9)	0.0745 (14)	0.0536 (11)	0.0014 (9)	0.0038 (8)	0.0170 (10)
C5	0.0358 (8)	0.0482 (10)	0.0363 (8)	−0.0078 (7)	0.0001 (6)	0.0113 (7)
N1	0.0328 (7)	0.0581 (9)	0.0340 (7)	−0.0079 (6)	−0.0066 (6)	0.0076 (6)
C6	0.0359 (7)	0.0334 (8)	0.0362 (8)	−0.0005 (6)	−0.0041 (6)	0.0105 (6)
C7	0.0308 (7)	0.0366 (8)	0.0408 (8)	0.0011 (6)	−0.0018 (6)	0.0104 (6)
C8	0.0348 (8)	0.0536 (11)	0.0492 (10)	−0.0023 (7)	−0.0088 (7)	0.0186 (8)
C9	0.0420 (8)	0.0497 (10)	0.0373 (8)	−0.0107 (7)	−0.0029 (7)	0.0130 (7)
C10	0.0333 (8)	0.0494 (10)	0.0496 (10)	0.0012 (7)	0.0043 (7)	0.0139 (8)
C11	0.0347 (7)	0.0421 (9)	0.0396 (8)	−0.0047 (6)	0.0059 (6)	0.0118 (7)
C12	0.0593 (11)	0.0457 (10)	0.0452 (10)	−0.0068 (8)	−0.0056 (8)	0.0103 (8)
C13	0.0661 (13)	0.0602 (13)	0.0611 (13)	−0.0029 (10)	−0.0127 (10)	0.0279 (11)
C14	0.0671 (13)	0.0521 (12)	0.0759 (15)	0.0095 (10)	0.0129 (11)	0.0299 (11)
C15	0.0749 (14)	0.0442 (11)	0.0595 (12)	0.0017 (10)	0.0226 (11)	0.0051 (9)
C16	0.0504 (10)	0.0523 (11)	0.0373 (8)	−0.0065 (8)	0.0080 (7)	0.0082 (7)
Cl1	0.0987 (5)	0.0856 (5)	0.0433 (3)	−0.0106 (4)	−0.0118 (3)	0.0007 (3)
O1	0.0450 (7)	0.0514 (7)	0.0370 (6)	−0.0043 (5)	−0.0015 (5)	0.0029 (5)
S1	0.0507 (3)	0.0646 (3)	0.0485 (3)	0.0007 (2)	−0.0081 (2)	0.0308 (2)

C1—C2	1.372 (4)	C8—S1	1.7554 (19)
C1—C9	1.393 (3)	C8—H8	0.9300
C1—H1	0.9300	C9—S1	1.767 (2)
C2—C3	1.373 (4)	C10—C11	1.510 (3)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.378 (3)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.390 (3)
C4—C5	1.387 (3)	C11—C16	1.393 (3)
C4—H4	0.9300	C12—C13	1.376 (3)
C5—C9	1.389 (2)	C12—H12	0.9300
C5—N1	1.414 (2)	C13—C14	1.366 (3)
N1—C6	1.347 (2)	C13—H13	0.9300
N1—H1A	0.81 (2)	C14—C15	1.371 (3)
C6—O1	1.236 (2)	C14—H14	0.9300
C6—C7	1.494 (2)	C15—C16	1.384 (3)
C7—C8	1.330 (2)	C15—H15	0.9300
C7—C10	1.513 (2)	C16—Cl1	1.740 (2)
C2—C1—C9	120.8 (2)	C5—C9—S1	121.50 (14)
C2—C1—H1	119.6	C1—C9—S1	119.38 (15)
C9—C1—H1	119.6	C11—C10—C7	111.24 (14)
C3—C2—C1	119.9 (2)	C11—C10—H10A	109.4
C3—C2—H2	120.0	C7—C10—H10A	109.4
C1—C2—H2	120.0	C11—C10—H10B	109.4
C2—C3—C4	120.2 (2)	C7—C10—H10B	109.4
C2—C3—H3	119.9	H10A—C10—H10B	108.0
C4—C3—H3	119.9	C12—C11—C16	116.03 (17)
C3—C4—C5	120.4 (2)	C12—C11—C10	120.21 (16)
C3—C4—H4	119.8	C16—C11—C10	123.74 (16)
C5—C4—H4	119.8	C13—C12—C11	122.1 (2)
C4—C5—C9	119.62 (17)	C13—C12—H12	118.9
C4—C5—N1	117.68 (16)	C11—C12—H12	118.9
C9—C5—N1	122.60 (17)	C14—C13—C12	120.3 (2)
C6—N1—C5	129.94 (14)	C14—C13—H13	119.8
C6—N1—H1A	112.3 (15)	C12—C13—H13	119.8
C5—N1—H1A	115.5 (16)	C13—C14—C15	119.7 (2)
O1—C6—N1	119.72 (14)	C13—C14—H14	120.2
O1—C6—C7	118.76 (15)	C15—C14—H14	120.2
N1—C6—C7	121.52 (14)	C14—C15—C16	119.7 (2)
C8—C7—C6	123.87 (16)	C14—C15—H15	120.1
C8—C7—C10	121.87 (15)	C16—C15—H15	120.1
C6—C7—C10	114.06 (14)	C15—C16—C11	122.12 (18)
C7—C8—S1	125.94 (14)	C15—C16—Cl1	118.14 (16)
C7—C8—H8	117.0	C11—C16—Cl1	119.73 (15)
S1—C8—H8	117.0	C8—S1—C9	99.34 (8)
C5—C9—C1	119.06 (19)
C9—C1—C2—C3	0.9 (4)	C2—C1—C9—S1	175.81 (18)
C1—C2—C3—C4	−0.1 (4)	C8—C7—C10—C11	119.48 (19)
C2—C3—C4—C5	−0.2 (4)	C6—C7—C10—C11	−65.55 (19)
C3—C4—C5—C9	−0.4 (3)	C7—C10—C11—C12	96.9 (2)
C3—C4—C5—N1	−176.6 (2)	C7—C10—C11—C16	−81.8 (2)
C4—C5—N1—C6	−131.9 (2)	C16—C11—C12—C13	0.9 (3)
C9—C5—N1—C6	52.0 (3)	C10—C11—C12—C13	−177.81 (19)
C5—N1—C6—O1	169.22 (17)	C11—C12—C13—C14	−0.7 (3)
C5—N1—C6—C7	−9.9 (3)	C12—C13—C14—C15	−0.4 (4)
O1—C6—C7—C8	136.80 (19)	C13—C14—C15—C16	1.3 (3)
N1—C6—C7—C8	−44.0 (3)	C14—C15—C16—C11	−1.1 (3)
O1—C6—C7—C10	−38.0 (2)	C14—C15—C16—Cl1	−179.98 (17)
N1—C6—C7—C10	141.13 (17)	C12—C11—C16—C15	0.0 (3)
C6—C7—C8—S1	7.7 (3)	C10—C11—C16—C15	178.67 (17)
C10—C7—C8—S1	−177.85 (14)	C12—C11—C16—Cl1	178.87 (14)
C4—C5—C9—C1	1.2 (3)	C10—C11—C16—Cl1	−2.4 (2)
N1—C5—C9—C1	177.26 (17)	C7—C8—S1—C9	55.28 (19)
C4—C5—C9—S1	−176.03 (15)	C5—C9—S1—C8	−59.33 (16)
N1—C5—C9—S1	0.0 (2)	C1—C9—S1—C8	123.43 (16)
C2—C1—C9—C5	−1.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.82 (2)	2.08 (2)	2.8911 (19)	174 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.82 (2)	2.08 (2)	2.8911 (19)	174 (3)

Symmetry code: (i) .