2-(3-Oxo-3,4-dihydro-2H-1,4-benzothia­zin-4-yl)acetamide

Saeed, A.; Mahmood, Z.; Yang, S.; Salim, M.; Akhtar, M.S.

doi:10.1107/S1600536810036305

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2567

doi:10.1107/S1600536810036305

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2-(3-Oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl)acetamide

Azher Saeed,^a ^* Zaid Mahmood,^a Shiyao Yang,^b Muhammad Salim ^a and Muhammad Saleem Akhtar ^c

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China, and ^cDepartment of Chemistry, Govt. Islamia College, Civil Lines, Lahore, Pakistan
^*Correspondence e-mail: azherch82003@yahoo.com

(Received 28 August 2010; accepted 10 September 2010; online 15 September 2010)

In the title compound, C₁₀H₁₀N₂O₂S, the thiazine 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 thiazine 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_r = 222.26
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.107
S = 1.02
2544 reflections
142 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) -x, -y+1, -z+1; (ii) x, y+1, z; (iii) x, y-1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

As part of our ongoing studies of 1,4-thiazine compounds (Saeed et al., 2010) we have synthesized 2-(3-oxo-2,3-dihydro benzo[b][1,4]thiazin-4-yl)acetamide for derivaziation and we report here the structure of the title compound.

The bond lengths and bond angles of the structure of the title compound is in comparison with our previously published structure of 2-(3-Oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl)acetohydrazide (II) (Saeed et al., 2010). These molecules only differ in amide (I) and hydrazide (II) groups attached to carbonyl carbon of acetate. The dihedral angle between the two rings C1–C6 and C1/C6/N1/C7/C8/S1 are almost same in these molecules i.e. 17.47 (0.09)° and 16.77 (0.10)° respectively. The amide group C9/C10/O2/N2 attached to the thiazine ring is oriented at dihedral angle of 72.05 (0.08)° and 88.83 (0.08)° with respect to the aromatic and thiazine ring. The amido hydrogens atoms are involved N–H···O type interactions with the oxygens of two different molecules. The N–H···O and weak C–H···O form dimers which results in 16 members ring motif R₂²(16) (Bernstein et al., 1995) along the b axes.

Related literature top

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

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I) with intermolecular hydrogen bonds shown by dashed lines. The hydrogen atom not involved in hydrogen bonding have been omitted for clarity.

2-(3-Oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl)acetamide top

Crystal data top

C₁₀H₁₀N₂O₂S	F(000) = 464
M_r = 222.26	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0425P)² + 0.2819P] where P = (F_o² + 2F_c²)/3
2544 reflections	(Δ/σ)_max < 0.001
142 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₀H₁₀N₂O₂S	V = 1017.58 (12) Å³
M_r = 222.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0652 (6) Å	µ = 0.30 mm⁻¹
b = 4.8415 (3) Å	T = 296 K
c = 26.1517 (19) Å	0.28 × 0.09 × 0.06 mm
β = 94.798 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2544 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1693 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.982	R_int = 0.039
11611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.24 e Å⁻³
2544 reflections	Δρ_min = −0.26 e Å⁻³
142 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1; (ii) x, y+1, z; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂O₂S
M_r	222.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.0652 (6), 4.8415 (3), 26.1517 (19)
β (°)	94.798 (4)
V (Å³)	1017.58 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.28 × 0.09 × 0.06

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.921, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	11611, 2544, 1693
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.107, 1.02
No. of reflections	2544
No. of parameters	142
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

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)	172.6

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y+1, z; (iii) x, y−1, z.

Acknowledgements

The authors acknowledge Higher Education Commission of Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN Code: 042-120614-PS2-128).

References

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