2-(3-Oxo-3,4-dihydro-2H-1,4-benzothia-zin-4-yl)acetamide.

In the title compound, C(10)H(10)N(2)O(2)S, the thia-zine ring approximates to an envelope form with the S atom in the flap position. The amide group attached to the acetate group is almost perpendicular to the mean plane of the thia-zine ring [dihedral angle = 88.83 (8)°]. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur. Further N-H⋯O and C-H⋯O hydrogen bonds link the dimers into a three-dimensional network.

Related literature

For a related structure and background references, see: Saeed et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶)

Experimental

Crystal data

C10H10N2O2S

M = 222.26

Monoclinic,

a = 8.0652 (6) Å

b = 4.8415 (3) Å

c = 26.1517 (19) Å

β = 94.798 (4)°

V = 1017.58 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.28 × 0.09 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.921, T max = 0.982

11611 measured reflections

2544 independent reflections

1693 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.02

2544 reflections

142 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036305/hb5628sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036305/hb5628Isup2.hkl

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

C10H10N2O2S	F(000) = 464
Mr = 222.26	Dx = 1.451 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2429 reflections
a = 8.0652 (6) Å	θ = 2.5–24.3°
b = 4.8415 (3) Å	µ = 0.30 mm−1
c = 26.1517 (19) Å	T = 296 K
β = 94.798 (4)°	Needle, colorless
V = 1017.58 (12) Å3	0.28 × 0.09 × 0.06 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2544 independent reflections
Radiation source: fine-focus sealed tube	1693 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.921, Tmax = 0.982	k = −6→6
11611 measured reflections	l = −34→34

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.2819P] where P = (Fo2 + 2Fc2)/3
2544 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. To a solution of (1.56 g)ethyl 2-(3-oxo-2,3-dihydrobenzo[b][1,4]thiazin-4-yl)- acetate in 10.0 ml ethanol, 5.0 ml of 33% ammonia was added and the mixture was left for a week at room temperature. The crystals of 2-(3-oxo-2,3-dihydrobenzo[1,4]thiazin-4-yl)acetamide appeared were filtered, washed with water and dried.(M.p 475k)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.3288 (2)	0.0539 (4)	0.31875 (7)	0.0388 (4)
C2	0.4502 (3)	−0.1224 (4)	0.30259 (9)	0.0529 (5)
H2	0.4358	−0.2023	0.2702	0.063*
C3	0.5914 (3)	−0.1799 (5)	0.33408 (10)	0.0584 (6)
H3	0.6726	−0.2962	0.3228	0.070*
C4	0.6121 (3)	−0.0650 (5)	0.38215 (9)	0.0530 (6)
H4	0.7083	−0.1011	0.4032	0.064*
C5	0.4909 (2)	0.1035 (4)	0.39939 (8)	0.0437 (5)
H5	0.5047	0.1759	0.4324	0.052*
C6	0.3480 (2)	0.1667 (3)	0.36793 (7)	0.0338 (4)
C7	0.0611 (2)	0.3388 (4)	0.36763 (7)	0.0378 (4)
C8	0.0096 (2)	0.1364 (4)	0.32606 (7)	0.0416 (4)
H8A	−0.1005	0.1838	0.3108	0.050*
H8B	0.0043	−0.0472	0.3407	0.050*
C9	0.2668 (3)	0.5317 (4)	0.42842 (7)	0.0419 (5)
H9A	0.2076	0.7047	0.4225	0.050*
H9B	0.3851	0.5713	0.4306	0.050*
C10	0.2227 (2)	0.4090 (3)	0.47892 (7)	0.0364 (4)
N1	0.22507 (19)	0.3468 (3)	0.38519 (6)	0.0361 (4)
N2	0.2048 (2)	0.5907 (4)	0.51556 (7)	0.0455 (4)
O1	−0.04093 (19)	0.4905 (3)	0.38558 (6)	0.0541 (4)
O2	0.2099 (2)	0.1598 (3)	0.48455 (6)	0.0621 (5)
S1	0.15349 (7)	0.13660 (13)	0.277323 (19)	0.05234 (19)
H1N	0.170 (3)	0.539 (5)	0.5448 (10)	0.063*
H2N	0.200 (3)	0.758 (5)	0.5079 (9)	0.063*

	U11	U22	U33	U12	U13	U23
C1	0.0372 (11)	0.0433 (10)	0.0364 (10)	−0.0020 (8)	0.0064 (8)	0.0017 (8)
C2	0.0504 (14)	0.0582 (13)	0.0518 (13)	0.0043 (11)	0.0148 (11)	−0.0085 (10)
C3	0.0427 (13)	0.0595 (13)	0.0757 (17)	0.0117 (11)	0.0204 (12)	0.0056 (12)
C4	0.0333 (12)	0.0619 (13)	0.0638 (14)	0.0005 (10)	0.0038 (10)	0.0158 (11)
C5	0.0363 (11)	0.0515 (11)	0.0430 (11)	−0.0067 (9)	0.0009 (9)	0.0047 (9)
C6	0.0341 (10)	0.0320 (8)	0.0360 (9)	−0.0051 (7)	0.0064 (8)	0.0037 (7)
C7	0.0421 (11)	0.0369 (9)	0.0354 (9)	0.0030 (8)	0.0097 (8)	0.0096 (8)
C8	0.0337 (10)	0.0518 (11)	0.0389 (10)	0.0008 (9)	0.0000 (8)	0.0045 (9)
C9	0.0567 (13)	0.0299 (9)	0.0395 (10)	−0.0068 (9)	0.0072 (9)	−0.0014 (8)
C10	0.0422 (11)	0.0288 (9)	0.0378 (10)	0.0007 (8)	0.0015 (8)	0.0012 (7)
N1	0.0407 (9)	0.0342 (8)	0.0339 (8)	−0.0020 (7)	0.0052 (7)	−0.0014 (6)
N2	0.0665 (13)	0.0331 (8)	0.0372 (9)	−0.0014 (8)	0.0064 (9)	0.0003 (7)
O1	0.0539 (10)	0.0549 (8)	0.0553 (9)	0.0169 (7)	0.0163 (8)	0.0037 (7)
O2	0.1082 (14)	0.0280 (7)	0.0531 (9)	−0.0020 (7)	0.0254 (9)	0.0033 (6)
S1	0.0471 (3)	0.0784 (4)	0.0311 (3)	0.0047 (3)	0.0010 (2)	−0.0017 (2)

C1—C2	1.391 (3)	C7—N1	1.364 (2)
C1—C6	1.394 (3)	C7—C8	1.496 (3)
C1—S1	1.754 (2)	C8—S1	1.794 (2)
C2—C3	1.377 (3)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.372 (3)	C9—N1	1.459 (2)
C3—H3	0.9300	C9—C10	1.517 (3)
C4—C5	1.377 (3)	C9—H9A	0.9700
C4—H4	0.9300	C9—H9B	0.9700
C5—C6	1.393 (3)	C10—O2	1.221 (2)
C5—H5	0.9300	C10—N2	1.318 (2)
C6—N1	1.422 (2)	N2—H1N	0.87 (3)
C7—O1	1.225 (2)	N2—H2N	0.84 (3)
C2—C1—C6	119.62 (19)	C7—C8—H8A	109.4
C2—C1—S1	120.25 (16)	S1—C8—H8A	109.4
C6—C1—S1	120.14 (15)	C7—C8—H8B	109.4
C3—C2—C1	120.7 (2)	S1—C8—H8B	109.4
C3—C2—H2	119.7	H8A—C8—H8B	108.0
C1—C2—H2	119.7	N1—C9—C10	112.25 (14)
C4—C3—C2	119.8 (2)	N1—C9—H9A	109.2
C4—C3—H3	120.1	C10—C9—H9A	109.2
C2—C3—H3	120.1	N1—C9—H9B	109.2
C3—C4—C5	120.3 (2)	C10—C9—H9B	109.2
C3—C4—H4	119.8	H9A—C9—H9B	107.9
C5—C4—H4	119.8	O2—C10—N2	123.82 (18)
C4—C5—C6	120.8 (2)	O2—C10—C9	121.34 (17)
C4—C5—H5	119.6	N2—C10—C9	114.82 (15)
C6—C5—H5	119.6	C7—N1—C6	123.91 (15)
C5—C6—C1	118.77 (17)	C7—N1—C9	115.64 (16)
C5—C6—N1	120.77 (17)	C6—N1—C9	120.03 (16)
C1—C6—N1	120.44 (17)	C10—N2—H1N	120.5 (16)
O1—C7—N1	121.15 (18)	C10—N2—H2N	118.6 (16)
O1—C7—C8	121.10 (19)	H1N—N2—H2N	119 (2)
N1—C7—C8	117.75 (16)	C1—S1—C8	95.57 (9)
C7—C8—S1	111.06 (13)
C6—C1—C2—C3	−2.0 (3)	N1—C9—C10—N2	−158.55 (18)
S1—C1—C2—C3	177.41 (17)	O1—C7—N1—C6	176.58 (16)
C1—C2—C3—C4	0.8 (3)	C8—C7—N1—C6	−2.8 (2)
C2—C3—C4—C5	1.2 (3)	O1—C7—N1—C9	4.0 (2)
C3—C4—C5—C6	−1.9 (3)	C8—C7—N1—C9	−175.37 (15)
C4—C5—C6—C1	0.6 (3)	C5—C6—N1—C7	−153.56 (17)
C4—C5—C6—N1	−178.24 (17)	C1—C6—N1—C7	27.6 (2)
C2—C1—C6—C5	1.3 (3)	C5—C6—N1—C9	18.7 (2)
S1—C1—C6—C5	−178.14 (14)	C1—C6—N1—C9	−160.18 (16)
C2—C1—C6—N1	−179.83 (17)	C10—C9—N1—C7	78.0 (2)
S1—C1—C6—N1	0.7 (2)	C10—C9—N1—C6	−94.8 (2)
O1—C7—C8—S1	136.66 (16)	C2—C1—S1—C8	142.29 (17)
N1—C7—C8—S1	−43.93 (19)	C6—C1—S1—C8	−38.29 (16)
N1—C9—C10—O2	23.3 (3)	C7—C8—S1—C1	57.82 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O1i	0.87 (3)	2.18 (3)	3.026 (2)	164 (2)
N2—H2N···O2ii	0.84 (3)	2.04 (3)	2.873 (2)	174 (2)
C8—H8B···O1iii	0.97	2.57	3.532 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯O1i	0.87 (3)	2.18 (3)	3.026 (2)	164 (2)
N2—H2N⋯O2ii	0.84 (3)	2.04 (3)	2.873 (2)	174 (2)
C8—H8B⋯O1iii	0.97	2.57	3.532 (2)	173

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