2-(4-Chloro-benzoyl-meth-yl)-2H-1,4-benzothia-zin-3(4H)-one.

The six-membered heterocyclic ring in the title compound, C(16)H(12)ClNO(2)S, exists in a conformation intermediate between twist-boat and chair. A one-dimensional chain structure is formed as a result of inter-molecular N-H⋯O and C-H⋯O hydrogen bonds via crystallographic inversion symmetry and translation along the a axis.

Related literature

For the synthesis and biological activities of related chalcones and 1,5-benzothia­zepines, see: Ansari et al. (2005 ▶); Pant et al. (2006 ▶). For microwave-assisted syntheses of related compounds, see: Dandia et al. (2002 ▶). For further related literature, see: Pant & Chugh (1989 ▶); Kirchner & Alexander (1959 ▶); Beryozkina et al. (2004 ▶); Pant et al. (1987 ▶).

Experimental

Crystal data

C16H12ClNO2S

M = 317.78

Triclinic,

a = 7.7273 (19) Å

b = 8.649 (2) Å

c = 12.298 (3) Å

α = 82.032 (3)°

β = 72.349 (2)°

γ = 68.829 (3)°

V = 730.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 273 (2) K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.876, T max = 1.000 (expected range = 0.814–0.929)

3962 measured reflections

2545 independent reflections

2236 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.06

2545 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007423/si2076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007423/si2076Isup2.hkl

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

C16H12ClNO2S	Z = 2
Mr = 317.78	F000 = 328
Triclinic, P1	Dx = 1.446 Mg m−3
a = 7.7273 (19) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.649 (2) Å	Cell parameters from 2700 reflections
c = 12.298 (3) Å	θ = 2.5–28.0º
α = 82.032 (3)º	µ = 0.41 mm−1
β = 72.349 (2)º	T = 273 (2) K
γ = 68.829 (3)º	Labellar, colorless
V = 730.0 (3) Å3	0.24 × 0.20 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	2545 independent reflections
Radiation source: fine-focus sealed tube	2236 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.009
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)	h = −9→9
Tmin = 0.876, Tmax = 1.000	k = −10→8
3962 measured reflections	l = −14→14

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0412P)2 + 0.2045P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2545 reflections	Δρmax = 0.18 e Å−3
190 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cl1	−0.60724 (7)	0.61069 (8)	0.87177 (5)	0.0776 (2)
S1	0.31357 (6)	0.84225 (6)	0.23145 (3)	0.04914 (15)
O1	0.30018 (15)	0.92709 (13)	0.52142 (9)	0.0402 (3)
O2	0.28795 (16)	0.57700 (15)	0.57928 (11)	0.0527 (3)
N1	0.54966 (17)	0.90262 (15)	0.36402 (11)	0.0373 (3)
H1	0.5980	0.9498	0.3985	0.045*
C1	0.6460 (2)	0.86774 (18)	0.24884 (13)	0.0363 (3)
C2	0.8326 (2)	0.8708 (2)	0.20508 (15)	0.0474 (4)
H2	0.8953	0.8892	0.2532	0.057*
C3	0.9255 (3)	0.8467 (2)	0.09073 (16)	0.0567 (5)
H3	1.0508	0.8488	0.0619	0.068*
C4	0.8333 (3)	0.8197 (3)	0.01912 (16)	0.0632 (5)
H4	0.8959	0.8043	−0.0582	0.076*
C5	0.6482 (3)	0.8155 (3)	0.06182 (15)	0.0571 (5)
H5	0.5869	0.7963	0.0132	0.069*
C6	0.5527 (2)	0.8397 (2)	0.17663 (13)	0.0418 (4)
C7	0.3290 (2)	0.75703 (18)	0.37328 (12)	0.0344 (3)
H7	0.4274	0.6463	0.3666	0.041*
C8	0.3893 (2)	0.87005 (17)	0.42642 (12)	0.0327 (3)
C9	0.1349 (2)	0.74330 (18)	0.44118 (12)	0.0353 (3)
H9A	0.0417	0.8540	0.4564	0.042*
H9B	0.0918	0.6900	0.3952	0.042*
C10	0.1384 (2)	0.64667 (18)	0.55313 (13)	0.0361 (3)
C11	−0.0490 (2)	0.63785 (17)	0.63063 (13)	0.0348 (3)
C12	−0.2165 (2)	0.68862 (19)	0.59542 (14)	0.0399 (4)
H12	−0.2133	0.7301	0.5212	0.048*
C13	−0.3878 (2)	0.6784 (2)	0.66903 (15)	0.0448 (4)
H13	−0.4992	0.7119	0.6448	0.054*
C14	−0.3901 (2)	0.6180 (2)	0.77841 (15)	0.0457 (4)
C15	−0.2254 (3)	0.5640 (2)	0.81540 (15)	0.0537 (4)
H15	−0.2293	0.5219	0.8896	0.064*
C16	−0.0555 (2)	0.5732 (2)	0.74112 (14)	0.0467 (4)
H16	0.0563	0.5357	0.7652	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.0481 (3)	0.1072 (5)	0.0628 (3)	−0.0307 (3)	0.0052 (2)	0.0103 (3)
S1	0.0396 (2)	0.0791 (3)	0.0395 (2)	−0.0307 (2)	−0.01448 (18)	0.0016 (2)
O1	0.0368 (6)	0.0468 (6)	0.0402 (6)	−0.0183 (5)	−0.0069 (5)	−0.0085 (5)
O2	0.0335 (6)	0.0611 (7)	0.0604 (8)	−0.0122 (5)	−0.0183 (5)	0.0097 (6)
N1	0.0339 (7)	0.0453 (7)	0.0402 (7)	−0.0202 (6)	−0.0103 (5)	−0.0062 (5)
C1	0.0336 (8)	0.0368 (8)	0.0399 (8)	−0.0150 (6)	−0.0090 (6)	0.0000 (6)
C2	0.0380 (9)	0.0573 (10)	0.0510 (10)	−0.0223 (8)	−0.0117 (7)	0.0011 (8)
C3	0.0409 (10)	0.0716 (12)	0.0548 (11)	−0.0273 (9)	−0.0001 (8)	0.0001 (9)
C4	0.0591 (12)	0.0848 (14)	0.0433 (10)	−0.0350 (11)	0.0042 (9)	−0.0065 (9)
C5	0.0593 (11)	0.0816 (13)	0.0404 (9)	−0.0376 (10)	−0.0095 (8)	−0.0051 (9)
C6	0.0378 (9)	0.0499 (9)	0.0403 (8)	−0.0205 (7)	−0.0080 (7)	−0.0003 (7)
C7	0.0299 (7)	0.0368 (8)	0.0389 (8)	−0.0132 (6)	−0.0095 (6)	−0.0036 (6)
C8	0.0284 (7)	0.0329 (7)	0.0381 (8)	−0.0099 (6)	−0.0121 (6)	0.0000 (6)
C9	0.0298 (8)	0.0371 (8)	0.0427 (8)	−0.0144 (6)	−0.0107 (6)	−0.0032 (6)
C10	0.0326 (8)	0.0345 (8)	0.0436 (8)	−0.0118 (6)	−0.0120 (6)	−0.0040 (6)
C11	0.0341 (8)	0.0318 (7)	0.0404 (8)	−0.0122 (6)	−0.0110 (6)	−0.0025 (6)
C12	0.0373 (8)	0.0420 (8)	0.0427 (8)	−0.0169 (7)	−0.0141 (7)	0.0078 (7)
C13	0.0346 (8)	0.0471 (9)	0.0542 (10)	−0.0166 (7)	−0.0147 (7)	0.0070 (7)
C14	0.0375 (9)	0.0491 (9)	0.0457 (9)	−0.0161 (7)	−0.0025 (7)	−0.0021 (7)
C15	0.0521 (11)	0.0704 (12)	0.0363 (9)	−0.0216 (9)	−0.0106 (8)	0.0047 (8)
C16	0.0418 (9)	0.0573 (10)	0.0431 (9)	−0.0155 (8)	−0.0170 (7)	0.0002 (7)

Cl1—C14	1.7394 (17)	C7—C8	1.5135 (19)
S1—C6	1.7573 (16)	C7—C9	1.5173 (19)
S1—C7	1.8182 (15)	C7—H7	0.9800
O1—C8	1.2284 (18)	C9—C10	1.511 (2)
O2—C10	1.2129 (18)	C9—H9A	0.9700
N1—C8	1.3489 (18)	C9—H9B	0.9700
N1—C1	1.403 (2)	C10—C11	1.494 (2)
N1—H1	0.8600	C11—C16	1.389 (2)
C1—C2	1.386 (2)	C11—C12	1.390 (2)
C1—C6	1.394 (2)	C12—C13	1.384 (2)
C2—C3	1.377 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.371 (2)
C3—C4	1.377 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.381 (3)
C4—C5	1.378 (3)	C15—C16	1.376 (2)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.386 (2)	C16—H16	0.9300
C5—H5	0.9300
C6—S1—C7	97.48 (7)	O1—C8—C7	122.41 (13)
C8—N1—C1	126.91 (12)	N1—C8—C7	116.00 (12)
C8—N1—H1	116.5	C10—C9—C7	113.70 (12)
C1—N1—H1	116.5	C10—C9—H9A	108.8
C2—C1—C6	119.70 (14)	C7—C9—H9A	108.8
C2—C1—N1	119.38 (14)	C10—C9—H9B	108.8
C6—C1—N1	120.82 (13)	C7—C9—H9B	108.8
C3—C2—C1	120.31 (16)	H9A—C9—H9B	107.7
C3—C2—H2	119.8	O2—C10—C11	120.79 (14)
C1—C2—H2	119.8	O2—C10—C9	121.44 (14)
C4—C3—C2	120.09 (16)	C11—C10—C9	117.77 (12)
C4—C3—H3	120.0	C16—C11—C12	118.65 (14)
C2—C3—H3	120.0	C16—C11—C10	118.96 (13)
C3—C4—C5	120.09 (17)	C12—C11—C10	122.38 (14)
C3—C4—H4	120.0	C13—C12—C11	121.08 (15)
C5—C4—H4	120.0	C13—C12—H12	119.5
C4—C5—C6	120.49 (17)	C11—C12—H12	119.5
C4—C5—H5	119.8	C14—C13—C12	118.69 (15)
C6—C5—H5	119.8	C14—C13—H13	120.7
C5—C6—C1	119.31 (15)	C12—C13—H13	120.7
C5—C6—S1	121.07 (13)	C13—C14—C15	121.61 (15)
C1—C6—S1	119.58 (12)	C13—C14—Cl1	118.54 (13)
C8—C7—C9	112.96 (12)	C15—C14—Cl1	119.85 (14)
C8—C7—S1	107.61 (10)	C16—C15—C14	119.17 (16)
C9—C7—S1	108.66 (10)	C16—C15—H15	120.4
C8—C7—H7	109.2	C14—C15—H15	120.4
C9—C7—H7	109.2	C15—C16—C11	120.77 (15)
S1—C7—H7	109.2	C15—C16—H16	119.6
O1—C8—N1	121.58 (13)	C11—C16—H16	119.6
C8—N1—C1—C2	−164.11 (15)	C9—C7—C8—N1	−172.83 (12)
C8—N1—C1—C6	19.6 (2)	S1—C7—C8—N1	−52.90 (15)
C6—C1—C2—C3	0.2 (3)	C8—C7—C9—C10	−70.81 (16)
N1—C1—C2—C3	−176.10 (16)	S1—C7—C9—C10	169.86 (10)
C1—C2—C3—C4	0.1 (3)	C7—C9—C10—O2	−5.5 (2)
C2—C3—C4—C5	−0.5 (3)	C7—C9—C10—C11	175.14 (12)
C3—C4—C5—C6	0.5 (3)	O2—C10—C11—C16	10.8 (2)
C4—C5—C6—C1	−0.2 (3)	C9—C10—C11—C16	−169.83 (14)
C4—C5—C6—S1	177.63 (15)	O2—C10—C11—C12	−167.67 (15)
C2—C1—C6—C5	−0.1 (2)	C9—C10—C11—C12	11.7 (2)
N1—C1—C6—C5	176.12 (15)	C16—C11—C12—C13	1.3 (2)
C2—C1—C6—S1	−178.03 (12)	C10—C11—C12—C13	179.77 (14)
N1—C1—C6—S1	−1.8 (2)	C11—C12—C13—C14	0.4 (2)
C7—S1—C6—C5	148.48 (15)	C12—C13—C14—C15	−1.5 (3)
C7—S1—C6—C1	−33.66 (14)	C12—C13—C14—Cl1	178.29 (12)
C6—S1—C7—C8	58.07 (11)	C13—C14—C15—C16	0.9 (3)
C6—S1—C7—C9	−179.31 (10)	Cl1—C14—C15—C16	−178.92 (14)
C1—N1—C8—O1	−169.12 (14)	C14—C15—C16—C11	0.8 (3)
C1—N1—C8—C7	12.0 (2)	C12—C11—C16—C15	−1.9 (2)
C9—C7—C8—O1	8.3 (2)	C10—C11—C16—C15	179.53 (15)
S1—C7—C8—O1	128.25 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.02	2.8812 (19)	177
C7—H7···O2ii	0.98	2.54	3.443 (2)	152
C9—H9A···O1iii	0.97	2.59	3.485 (2)	153
C13—H13···O1iv	0.93	2.59	3.400 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.02	2.8812 (19)	177
C7—H7⋯O2ii	0.98	2.54	3.443 (2)	152
C9—H9A⋯O1iii	0.97	2.59	3.485 (2)	153
C13—H13⋯O1iv	0.93	2.59	3.400 (2)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .