(Z)-3-(2,4-Dichloro-benz-yl)-1,5-benzo-thia-zepin-4(5H)-one.

In the title compound, C16H11Cl2NOS, the seven-membered thia-zepine ring adopts a distorted twist-boat conformation. The dihedral angle between the mean plane of the benzothia-zepine ring system and the benzene ring is 78.6 (1)°. The mol-ecular conformation is stabilized by a weak intra-molecular C-H⋯Cl hydrogen bond, which generates an S(5) ring motif. In the crystal, pairs of N-H⋯O hydrogen bonds link inversion-related mol-ecules into dimers, generating R 2 (2)(8) ring motifs. The crystal packing also features alternating π-π inter-actions between benzothia-zepine benzene rings [inter-centroid distance = 3.740 (3) Å] and dichloro-benzene rings [inter-centroid distance = 3.882 (3) Å] to consolidate a three-dimensional architecture.

Related literature

For background to the biology and related structures of thia­zepin derivatives, see: Bakthadoss et al. (2013 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H11Cl2NOS

M = 336.22

Triclinic,

a = 7.879 (5) Å

b = 9.667 (5) Å

c = 9.979 (5) Å

α = 89.052 (5)°

β = 78.161 (4)°

γ = 83.647 (5)°

V = 739.3 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.58 mm−1

T = 293 K

0.24 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.871, T max = 0.917

18415 measured reflections

5225 independent reflections

4013 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.123

S = 1.04

5225 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.44 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007435/tk5208sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007435/tk5208Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007435/tk5208Isup3.cml

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

C16H11Cl2NOS	Z = 2
Mr = 336.22	F(000) = 344
Triclinic, P1	Dx = 1.510 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.879 (5) Å	Cell parameters from 5914 reflections
b = 9.667 (5) Å	θ = 2.1–33.7°
c = 9.979 (5) Å	µ = 0.58 mm−1
α = 89.052 (5)°	T = 293 K
β = 78.161 (4)°	Block, colourless
γ = 83.647 (5)°	0.24 × 0.21 × 0.15 mm
V = 739.3 (7) Å3

Bruker APEXII CCD diffractometer	5225 independent reflections
Radiation source: fine-focus sealed tube	4013 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 33.7°, θmin = 2.1°
ω scans	h = −12→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.871, Tmax = 0.917	l = −14→15
18415 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.2157P] where P = (Fo2 + 2Fc2)/3
5225 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.44 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	0.53450 (18)	0.28937 (15)	0.94205 (15)	0.0366 (3)
H1	0.4546	0.2673	0.8911	0.044*
C2	0.6952 (2)	0.14986 (15)	1.12880 (14)	0.0371 (3)
C3	0.6971 (3)	0.01550 (17)	1.18247 (17)	0.0510 (4)
H3	0.5951	−0.0277	1.1996	0.061*
C4	0.8473 (3)	−0.05324 (19)	1.21016 (19)	0.0622 (5)
H4	0.8466	−0.1424	1.2467	0.075*
C5	0.9993 (3)	0.0092 (2)	1.18406 (19)	0.0600 (5)
H5	1.1010	−0.0374	1.2038	0.072*
C6	1.0008 (2)	0.14161 (19)	1.12835 (17)	0.0469 (3)
H6	1.1037	0.1836	1.1106	0.056*
C7	0.84959 (19)	0.21138 (14)	1.09904 (14)	0.0352 (3)
C8	0.79730 (18)	0.41136 (14)	0.94238 (15)	0.0349 (3)
C9	0.66727 (17)	0.35381 (13)	0.87569 (14)	0.0321 (2)
C10	0.6884 (2)	0.39317 (17)	0.72620 (15)	0.0423 (3)
H10A	0.6968	0.4924	0.7186	0.051*
H10B	0.7978	0.3460	0.6767	0.051*
C11	0.5449 (2)	0.35964 (15)	0.65712 (14)	0.0371 (3)
C12	0.55727 (19)	0.24270 (15)	0.57559 (15)	0.0359 (3)
C13	0.42879 (19)	0.21821 (15)	0.50589 (15)	0.0388 (3)
H13	0.4419	0.1402	0.4499	0.047*
C14	0.28122 (19)	0.31163 (16)	0.52118 (14)	0.0390 (3)
C15	0.2600 (2)	0.42737 (18)	0.60401 (18)	0.0477 (4)
H15	0.1583	0.4886	0.6158	0.057*
C16	0.3933 (2)	0.45071 (17)	0.66928 (17)	0.0469 (4)
H16	0.3808	0.5302	0.7232	0.056*
N1	0.85975 (16)	0.34776 (12)	1.04633 (13)	0.0375 (3)
H1A	0.9155	0.3990	1.0879	0.045*
O1	0.84965 (17)	0.52292 (12)	0.89978 (14)	0.0545 (3)
Cl1	0.73749 (6)	0.11906 (5)	0.55837 (6)	0.06427 (15)
Cl2	0.11969 (6)	0.27905 (6)	0.43563 (5)	0.05837 (14)
S1	0.49323 (5)	0.24136 (4)	1.11466 (4)	0.04389 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0354 (7)	0.0435 (7)	0.0355 (7)	−0.0151 (5)	−0.0122 (5)	0.0003 (5)
C2	0.0443 (7)	0.0377 (6)	0.0304 (6)	−0.0118 (5)	−0.0059 (5)	0.0013 (5)
C3	0.0692 (11)	0.0425 (8)	0.0405 (8)	−0.0178 (8)	−0.0032 (7)	0.0067 (6)
C4	0.0933 (16)	0.0444 (9)	0.0444 (9)	−0.0023 (9)	−0.0077 (9)	0.0139 (7)
C5	0.0720 (13)	0.0603 (11)	0.0463 (9)	0.0113 (9)	−0.0196 (9)	0.0086 (8)
C6	0.0460 (8)	0.0559 (9)	0.0417 (8)	−0.0047 (7)	−0.0169 (7)	0.0046 (7)
C7	0.0413 (7)	0.0372 (6)	0.0298 (6)	−0.0090 (5)	−0.0111 (5)	0.0016 (5)
C8	0.0351 (6)	0.0342 (6)	0.0405 (7)	−0.0127 (5)	−0.0153 (5)	0.0023 (5)
C9	0.0344 (6)	0.0322 (6)	0.0339 (6)	−0.0106 (5)	−0.0129 (5)	−0.0001 (5)
C10	0.0475 (8)	0.0506 (8)	0.0355 (7)	−0.0246 (7)	−0.0142 (6)	0.0037 (6)
C11	0.0453 (7)	0.0411 (7)	0.0295 (6)	−0.0162 (6)	−0.0121 (5)	0.0028 (5)
C12	0.0359 (7)	0.0376 (6)	0.0369 (7)	−0.0105 (5)	−0.0103 (5)	0.0015 (5)
C13	0.0416 (7)	0.0419 (7)	0.0367 (7)	−0.0144 (6)	−0.0114 (6)	−0.0024 (5)
C14	0.0392 (7)	0.0492 (8)	0.0328 (6)	−0.0151 (6)	−0.0121 (5)	0.0086 (5)
C15	0.0457 (8)	0.0507 (9)	0.0466 (8)	0.0005 (7)	−0.0122 (7)	−0.0001 (7)
C16	0.0563 (10)	0.0449 (8)	0.0416 (8)	−0.0057 (7)	−0.0144 (7)	−0.0072 (6)
N1	0.0406 (6)	0.0388 (6)	0.0405 (6)	−0.0169 (5)	−0.0194 (5)	0.0046 (5)
O1	0.0638 (8)	0.0471 (6)	0.0703 (8)	−0.0323 (6)	−0.0422 (6)	0.0212 (5)
Cl1	0.0451 (2)	0.0557 (3)	0.0965 (4)	0.00095 (18)	−0.0269 (2)	−0.0159 (2)
Cl2	0.0465 (2)	0.0776 (3)	0.0608 (3)	−0.0192 (2)	−0.0275 (2)	0.0075 (2)
S1	0.03570 (19)	0.0574 (2)	0.0392 (2)	−0.01553 (16)	−0.00402 (14)	0.00582 (15)

C1—C9	1.3294 (19)	C8—C9	1.4901 (18)
C1—S1	1.7508 (17)	C9—C10	1.514 (2)
C1—H1	0.9300	C10—C11	1.505 (2)
C2—C7	1.388 (2)	C10—H10A	0.9700
C2—C3	1.396 (2)	C10—H10B	0.9700
C2—S1	1.7642 (18)	C11—C12	1.387 (2)
C3—C4	1.368 (3)	C11—C16	1.389 (2)
C3—H3	0.9300	C12—C13	1.383 (2)
C4—C5	1.376 (3)	C12—Cl1	1.7336 (17)
C4—H4	0.9300	C13—C14	1.375 (2)
C5—C6	1.387 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.377 (2)
C6—C7	1.385 (2)	C14—Cl2	1.7295 (16)
C6—H6	0.9300	C15—C16	1.384 (2)
C7—N1	1.4158 (19)	C15—H15	0.9300
C8—O1	1.2350 (17)	C16—H16	0.9300
C8—N1	1.3481 (19)	N1—H1A	0.8600
C9—C1—S1	127.26 (11)	C11—C10—H10A	108.3
C9—C1—H1	116.4	C9—C10—H10A	108.3
S1—C1—H1	116.4	C11—C10—H10B	108.3
C7—C2—C3	119.11 (15)	C9—C10—H10B	108.3
C7—C2—S1	121.99 (12)	H10A—C10—H10B	107.4
C3—C2—S1	118.67 (13)	C12—C11—C16	116.63 (14)
C4—C3—C2	120.73 (17)	C12—C11—C10	123.35 (15)
C4—C3—H3	119.6	C16—C11—C10	119.97 (14)
C2—C3—H3	119.6	C13—C12—C11	122.51 (14)
C3—C4—C5	120.14 (17)	C13—C12—Cl1	117.07 (12)
C3—C4—H4	119.9	C11—C12—Cl1	120.42 (12)
C5—C4—H4	119.9	C14—C13—C12	118.59 (14)
C4—C5—C6	119.97 (18)	C14—C13—H13	120.7
C4—C5—H5	120.0	C12—C13—H13	120.7
C6—C5—H5	120.0	C13—C14—C15	121.28 (14)
C7—C6—C5	120.20 (17)	C13—C14—Cl2	118.34 (12)
C7—C6—H6	119.9	C15—C14—Cl2	120.38 (13)
C5—C6—H6	119.9	C14—C15—C16	118.61 (16)
C6—C7—C2	119.78 (14)	C14—C15—H15	120.7
C6—C7—N1	117.04 (13)	C16—C15—H15	120.7
C2—C7—N1	123.08 (13)	C15—C16—C11	122.33 (15)
O1—C8—N1	118.83 (12)	C15—C16—H16	118.8
O1—C8—C9	117.93 (12)	C11—C16—H16	118.8
N1—C8—C9	123.23 (12)	C8—N1—C7	131.25 (11)
C1—C9—C8	124.33 (13)	C8—N1—H1A	114.4
C1—C9—C10	122.86 (12)	C7—N1—H1A	114.4
C8—C9—C10	112.36 (11)	C1—S1—C2	101.45 (7)
C11—C10—C9	115.75 (12)
C7—C2—C3—C4	2.3 (2)	C16—C11—C12—C13	1.8 (2)
S1—C2—C3—C4	−172.38 (14)	C10—C11—C12—C13	−175.75 (13)
C2—C3—C4—C5	−0.6 (3)	C16—C11—C12—Cl1	−177.66 (12)
C3—C4—C5—C6	−0.6 (3)	C10—C11—C12—Cl1	4.7 (2)
C4—C5—C6—C7	0.1 (3)	C11—C12—C13—C14	−1.8 (2)
C5—C6—C7—C2	1.6 (2)	Cl1—C12—C13—C14	177.71 (11)
C5—C6—C7—N1	178.10 (15)	C12—C13—C14—C15	−0.1 (2)
C3—C2—C7—C6	−2.8 (2)	C12—C13—C14—Cl2	−179.09 (11)
S1—C2—C7—C6	171.71 (12)	C13—C14—C15—C16	1.9 (2)
C3—C2—C7—N1	−179.04 (14)	Cl2—C14—C15—C16	−179.17 (13)
S1—C2—C7—N1	−4.5 (2)	C14—C15—C16—C11	−1.8 (3)
S1—C1—C9—C8	−7.0 (2)	C12—C11—C16—C15	0.0 (2)
S1—C1—C9—C10	−178.71 (12)	C10—C11—C16—C15	177.70 (15)
O1—C8—C9—C1	−141.76 (16)	O1—C8—N1—C7	−167.01 (16)
N1—C8—C9—C1	38.2 (2)	C9—C8—N1—C7	13.1 (2)
O1—C8—C9—C10	30.69 (19)	C6—C7—N1—C8	135.73 (17)
N1—C8—C9—C10	−149.37 (15)	C2—C7—N1—C8	−47.9 (2)
C1—C9—C10—C11	2.2 (2)	C9—C1—S1—C2	−51.65 (16)
C8—C9—C10—C11	−170.34 (13)	C7—C2—S1—C1	58.57 (13)
C9—C10—C11—C12	−98.99 (18)	C3—C2—S1—C1	−126.89 (13)
C9—C10—C11—C16	83.49 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···Cl1	0.97	2.64	3.103 (3)	109
N1—H1A···O1i	0.86	2.10	2.873 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯Cl1	0.97	2.64	3.103 (3)	109
N1—H1A⋯O1i	0.86	2.10	2.873 (2)	149

Symmetry code: (i) .