Methyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzothia-zin-4-yl)acetate.

In the crystal structure of the title compound, C(11)H(11)NO(3)S, the mol-ecules are linked by inter-molecular C-H⋯O hydrogen-bond inter-actions. The heterocyclic thia-zine ring adopts a conformation inter-mediate between twist and boat.

Related literature

For general background to the synthesis of benzothia­zines, see: Harmata et al. (2005 ▶). For the pharmacological activity of benzothia­zine derivatives, see: Lopatina et al. (1982 ▶). For related structures, see: Saeed et al. (2010 ▶); Aouine et al. (2010 ▶).

Experimental

Crystal data

C11H11NO3S

M = 237.27

Monoclinic,

a = 17.347 (5) Å

b = 8.724 (2) Å

c = 7.274 (1) Å

β = 98.71 (2)°

V = 1088.1 (4) Å3

Z = 4

Cu Kα radiation

μ = 2.59 mm−1

T = 296 K

0.20 × 0.15 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.625, T max = 0.697

1852 measured reflections

1852 independent reflections

1654 reflections with I > 2σ(I)

2 standard reflections every 90 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.03

1852 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006477/bt5472sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006477/bt5472Isup2.hkl

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

C11H11NO3S	F(000) = 496
Mr = 237.27	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 17.347 (5) Å	θ = 25.0–35.0°
b = 8.724 (2) Å	µ = 2.59 mm−1
c = 7.274 (1) Å	T = 296 K
β = 98.71 (2)°	Prism, colourless
V = 1088.1 (4) Å3	0.20 × 0.15 × 0.15 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1654 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
graphite	θmax = 64.9°, θmin = 2.6°
ω–2θ scans	h = −20→20
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.625, Tmax = 0.697	l = 0→8
1852 measured reflections	2 standard reflections every 90 min
1852 independent reflections	intensity decay: none

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0891P)2 + 0.2952P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1852 reflections	Δρmax = 0.31 e Å−3
147 parameters	Δρmin = −0.28 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: 0.025 (2)

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	0.06412 (11)	1.0010 (2)	−0.1876 (3)	0.0408 (5)
C12	0.34845 (11)	0.9981 (2)	−0.1202 (3)	0.0425 (5)
C13	0.38184 (11)	1.1551 (2)	−0.0708 (3)	0.0385 (5)
C16	0.48971 (13)	1.3152 (3)	−0.0896 (3)	0.0523 (6)
C2	0.06020 (13)	1.0995 (2)	−0.3366 (3)	0.0462 (5)
C3	0.12837 (14)	1.1575 (2)	−0.3843 (3)	0.0477 (5)
C4	0.19978 (12)	1.1181 (2)	−0.2852 (3)	0.0411 (5)
C5	0.13542 (10)	0.9596 (2)	−0.0860 (2)	0.0342 (4)
C6	0.20474 (10)	1.0183 (2)	−0.1350 (2)	0.0325 (4)
C8	0.29001 (11)	0.9244 (2)	0.1449 (3)	0.0424 (5)
C9	0.22014 (12)	0.9212 (3)	0.2432 (3)	0.0480 (5)
H1	0.0183	0.9615	−0.1545	0.049*
H12A	0.3363	0.9889	−0.2544	0.051*
H12B	0.3870	0.9207	−0.0761	0.051*
H16A	0.4570	1.3905	−0.1589	0.078*
H16B	0.5394	1.3128	−0.1325	0.078*
H16C	0.4970	1.3413	0.0401	0.078*
H2	0.0122	1.1265	−0.4041	0.055*
H3	0.1262	1.2242	−0.4847	0.057*
H4	0.2451	1.1588	−0.3192	0.049*
H9A	0.2064	1.0251	0.2730	0.058*
H9B	0.2327	0.8649	0.3589	0.058*
N7	0.27801 (9)	0.97159 (18)	−0.0378 (2)	0.0371 (4)
O11	0.35438 (9)	0.8896 (2)	0.2240 (2)	0.0645 (5)
O14	0.34929 (8)	1.25486 (18)	−0.0003 (2)	0.0561 (5)
O15	0.45320 (8)	1.16608 (16)	−0.1160 (2)	0.0454 (4)
S10	0.13827 (3)	0.83215 (6)	0.10137 (7)	0.0470 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0361 (10)	0.0407 (10)	0.0462 (11)	−0.0021 (8)	0.0082 (8)	−0.0077 (8)
C2	0.0487 (11)	0.0415 (11)	0.0450 (11)	0.0044 (9)	−0.0043 (9)	−0.0055 (9)
C3	0.0651 (14)	0.0391 (11)	0.0370 (10)	−0.0035 (9)	0.0012 (9)	0.0033 (8)
C4	0.0502 (11)	0.0370 (10)	0.0385 (10)	−0.0082 (9)	0.0144 (8)	0.0011 (8)
C5	0.0378 (9)	0.0294 (9)	0.0373 (10)	−0.0026 (7)	0.0121 (7)	−0.0040 (7)
C6	0.0359 (9)	0.0287 (9)	0.0343 (9)	−0.0022 (7)	0.0098 (7)	−0.0042 (7)
N7	0.0312 (8)	0.0376 (8)	0.0447 (9)	−0.0005 (6)	0.0128 (6)	0.0019 (7)
C8	0.0408 (10)	0.0393 (10)	0.0471 (11)	0.0024 (8)	0.0071 (8)	0.0026 (8)
C9	0.0509 (11)	0.0567 (13)	0.0379 (10)	0.0024 (10)	0.0116 (9)	0.0121 (9)
S10	0.0442 (4)	0.0470 (4)	0.0529 (4)	−0.0048 (2)	0.0170 (2)	0.0152 (2)
O11	0.0449 (9)	0.0783 (12)	0.0667 (11)	0.0108 (8)	−0.0030 (7)	0.0096 (9)
C12	0.0334 (9)	0.0418 (11)	0.0560 (12)	0.0009 (8)	0.0185 (8)	−0.0028 (9)
C13	0.0295 (9)	0.0454 (11)	0.0419 (10)	−0.0017 (8)	0.0098 (7)	−0.0010 (8)
O14	0.0455 (9)	0.0543 (10)	0.0735 (11)	−0.0063 (7)	0.0257 (8)	−0.0220 (8)
O15	0.0317 (7)	0.0491 (8)	0.0579 (9)	−0.0035 (5)	0.0147 (6)	0.0000 (6)
C16	0.0405 (11)	0.0562 (13)	0.0605 (13)	−0.0111 (9)	0.0085 (10)	0.0037 (11)

S10—C5	1.7538 (17)	C5—C6	1.402 (2)
S10—C9	1.800 (2)	C8—C9	1.498 (3)
O11—C8	1.215 (3)	C12—C13	1.509 (3)
O14—C13	1.195 (2)	C1—H1	0.9300
O15—C13	1.332 (2)	C2—H2	0.9300
O15—C16	1.447 (3)	C3—H3	0.9300
N7—C6	1.418 (2)	C4—H4	0.9300
N7—C8	1.377 (3)	C9—H9A	0.9700
N7—C12	1.459 (3)	C9—H9B	0.9700
C1—C2	1.377 (3)	C12—H12A	0.9700
C1—C5	1.389 (3)	C12—H12B	0.9700
C2—C3	1.378 (3)	C16—H16A	0.9600
C3—C4	1.379 (3)	C16—H16B	0.9600
C4—C6	1.390 (3)	C16—H16C	0.9600
C5—S10—C9	95.67 (10)	C5—C1—H1	120.00
C13—O15—C16	115.88 (16)	C1—C2—H2	120.00
C6—N7—C8	124.10 (15)	C3—C2—H2	121.00
C6—N7—C12	119.55 (15)	C2—C3—H3	120.00
C8—N7—C12	115.50 (16)	C4—C3—H3	120.00
C2—C1—C5	121.00 (18)	C3—C4—H4	120.00
C1—C2—C3	119.0 (2)	C6—C4—H4	120.00
C2—C3—C4	120.93 (19)	S10—C9—H9A	109.00
C3—C4—C6	120.73 (19)	S10—C9—H9B	109.00
S10—C5—C1	119.76 (14)	C8—C9—H9A	109.00
S10—C5—C6	120.32 (13)	C8—C9—H9B	109.00
C1—C5—C6	119.92 (15)	H9A—C9—H9B	108.00
N7—C6—C4	121.09 (16)	N7—C12—H12A	109.00
N7—C6—C5	120.47 (14)	N7—C12—H12B	109.00
C4—C6—C5	118.39 (16)	C13—C12—H12A	109.00
O11—C8—N7	121.72 (18)	C13—C12—H12B	109.00
O11—C8—C9	121.43 (19)	H12A—C12—H12B	108.00
N7—C8—C9	116.83 (17)	O15—C16—H16A	109.00
S10—C9—C8	111.08 (15)	O15—C16—H16B	109.00
N7—C12—C13	111.18 (16)	O15—C16—H16C	109.00
O14—C13—O15	124.83 (17)	H16A—C16—H16B	109.00
O14—C13—C12	125.04 (18)	H16A—C16—H16C	109.00
O15—C13—C12	110.13 (16)	H16B—C16—H16C	109.00
C2—C1—H1	119.00

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O14i	0.93	2.51	3.411 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O14	0.93	2.51	3.411 (3)	164