Literature DB >> 21588642

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

Azher Saeed, Zaid Mahmood, Shiyao Yang, Saeed Ahmad, Muhammad Salim.

Abstract

In the title compound, C(10)H(11)N(3)O(2)S, the thia-zine ring exists in a conformation inter-mediate between twist-boat and half-chair. The dihedral angle between the mean plane of the thia-zine ring and the hydrazide group is 89.45 (13)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into (100) sheets and weak C-H⋯O inter-actions further consolidate the packing.

Entities: Chemical Disease Species

Year: 2010 PMID： 21588642 PMCID： PMC3008126 DOI： 10.1107/S1600536810031272

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological and medicinal activity of 1,4-benzothiazine compounds, see: Armenise et al. (1991 ▶); Gupta et al. (1993 ▶); Vicente et al. (2009 ▶); Schiaffella et al. (2006 ▶); Kaneko et al. (2002 ▶). For the pharmacological properties of hydrazones and their derivatives, see: Sivasankar et al. (1995 ▶); Satyanarayana et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H11N3O2S M = 237.28 Monoclinic, a = 15.3744 (10) Å b = 7.5162 (5) Å c = 9.6256 (7) Å β = 95.413 (3)° V = 1107.35 (13) Å3 Z = 4 Mo Kα radiation μ = 0.28 mm−1 T = 296 K 0.46 × 0.23 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.882, T max = 0.946 6103 measured reflections 2168 independent reflections 2077 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 0.076 S = 1.04 2168 reflections 157 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.18 e Å−3 Δρmin = −0.14 e Å−3 Absolute structure: Flack (1983 ▶), 792 Friedel pairs Flack parameter: 0.00 (7) 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: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031272/hb5598sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031272/hb5598Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₀H₁₁N₃O₂S	F(000) = 496
M_r = 237.28	D_x = 1.423 Mg m⁻³
Monoclinic, Cc	Melting point: 430 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 15.3744 (10) Å	Cell parameters from 4206 reflections
b = 7.5162 (5) Å	θ = 3.0–31.2°
c = 9.6256 (7) Å	µ = 0.28 mm⁻¹
β = 95.413 (3)°	T = 296 K
V = 1107.35 (13) Å³	Needle, colorless
Z = 4	0.46 × 0.23 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2168 independent reflections
Radiation source: fine-focus sealed tube	2077 reflections with I > 2σ(I)
graphite	R_int = 0.021
φ and ω scans	θ_max = 28.4°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→20
T_min = 0.882, T_max = 0.946	k = −8→10
6103 measured reflections	l = −12→10

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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0437P)² + 0.2667P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2168 reflections	Δρ_max = 0.18 e Å⁻³
157 parameters	Δρ_min = −0.14 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 792 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (7)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
C1	0.81283 (13)	0.1402 (3)	0.4407 (2)	0.0444 (4)
C2	0.88393 (15)	0.1642 (4)	0.3624 (3)	0.0684 (7)
H2	0.9061	0.0674	0.3170	0.082*
C3	0.92138 (15)	0.3276 (5)	0.3514 (3)	0.0727 (7)
H3	0.9691	0.3412	0.2998	0.087*
C4	0.88855 (14)	0.4717 (4)	0.4166 (3)	0.0621 (6)
H4	0.9145	0.5827	0.4099	0.074*
C5	0.81688 (12)	0.4524 (2)	0.4924 (2)	0.0451 (4)
H5	0.7944	0.5514	0.5347	0.054*
C6	0.77806 (10)	0.2868 (2)	0.50596 (15)	0.0325 (3)
C7	0.64582 (13)	0.1320 (2)	0.56774 (18)	0.0393 (4)
C8	0.65696 (13)	−0.0005 (2)	0.4532 (2)	0.0473 (4)
H8A	0.6398	0.0537	0.3633	0.057*
H8B	0.6194	−0.1024	0.4638	0.057*
C9	0.68864 (12)	0.3985 (2)	0.69169 (16)	0.0371 (4)
H9A	0.7419	0.4638	0.7190	0.044*
H9B	0.6710	0.3388	0.7738	0.044*
C10	0.61760 (11)	0.52828 (19)	0.63748 (15)	0.0311 (3)
N1	0.70588 (9)	0.26545 (17)	0.58681 (13)	0.0328 (3)
N2	0.57596 (11)	0.60513 (19)	0.73773 (16)	0.0391 (3)
N3	0.50598 (12)	0.7263 (3)	0.70912 (19)	0.0491 (4)
O1	0.60169 (9)	0.56431 (16)	0.51324 (12)	0.0441 (3)
O2	0.58443 (11)	0.1213 (2)	0.63853 (16)	0.0602 (4)
S1	0.76839 (4)	−0.07275 (6)	0.45907 (6)	0.06435 (19)
H1N	0.5831 (14)	0.561 (3)	0.822 (3)	0.036 (5)*
H2N	0.4722 (19)	0.678 (4)	0.641 (3)	0.072 (9)*
H3N	0.5321 (18)	0.834 (4)	0.681 (3)	0.065 (8)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0391 (9)	0.0492 (9)	0.0446 (10)	0.0071 (7)	0.0020 (8)	−0.0098 (8)
C2	0.0384 (11)	0.108 (2)	0.0598 (13)	0.0113 (12)	0.0099 (10)	−0.0256 (14)
C3	0.0360 (10)	0.126 (2)	0.0580 (14)	−0.0063 (14)	0.0133 (9)	0.0076 (15)
C4	0.0409 (10)	0.0773 (15)	0.0673 (14)	−0.0139 (10)	0.0019 (10)	0.0272 (12)
C5	0.0411 (10)	0.0407 (9)	0.0531 (12)	−0.0021 (8)	0.0022 (8)	0.0107 (8)
C6	0.0334 (8)	0.0347 (7)	0.0288 (8)	0.0042 (6)	0.0004 (6)	0.0033 (6)
C7	0.0462 (10)	0.0359 (8)	0.0360 (9)	−0.0013 (7)	0.0057 (7)	0.0027 (7)
C8	0.0532 (11)	0.0358 (9)	0.0529 (11)	−0.0081 (7)	0.0049 (8)	−0.0080 (7)
C9	0.0463 (9)	0.0382 (8)	0.0266 (8)	0.0068 (7)	0.0026 (7)	−0.0034 (6)
C10	0.0391 (8)	0.0292 (7)	0.0253 (7)	−0.0012 (6)	0.0052 (6)	−0.0015 (5)
N1	0.0393 (7)	0.0293 (6)	0.0304 (7)	0.0025 (5)	0.0068 (6)	−0.0012 (5)
N2	0.0516 (9)	0.0405 (7)	0.0261 (7)	0.0102 (6)	0.0081 (6)	0.0003 (6)
N3	0.0518 (10)	0.0517 (10)	0.0455 (9)	0.0147 (8)	0.0134 (8)	0.0016 (8)
O1	0.0585 (8)	0.0504 (7)	0.0239 (6)	0.0137 (6)	0.0059 (5)	0.0007 (5)
O2	0.0559 (9)	0.0728 (9)	0.0553 (9)	−0.0161 (7)	0.0223 (7)	−0.0008 (8)
S1	0.0661 (3)	0.0354 (2)	0.0898 (4)	0.0116 (2)	−0.0018 (3)	−0.0191 (3)

C1—C2	1.397 (3)	C7—C8	1.508 (3)
C1—C6	1.400 (2)	C8—S1	1.793 (2)
C1—S1	1.756 (2)	C8—H8A	0.9700
C2—C3	1.364 (4)	C8—H8B	0.9700
C2—H2	0.9300	C9—N1	1.463 (2)
C3—C4	1.372 (4)	C9—C10	1.520 (2)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.385 (3)	C9—H9B	0.9700
C4—H4	0.9300	C10—O1	1.228 (2)
C5—C6	1.392 (2)	C10—N2	1.338 (2)
C5—H5	0.9300	N2—N3	1.417 (2)
C6—N1	1.423 (2)	N2—H1N	0.87 (2)
C7—O2	1.218 (2)	N3—H2N	0.87 (3)
C7—N1	1.364 (2)	N3—H3N	0.96 (3)

C2—C1—C6	119.5 (2)	S1—C8—H8A	109.5
C2—C1—S1	120.28 (17)	C7—C8—H8B	109.5
C6—C1—S1	120.24 (15)	S1—C8—H8B	109.5
C3—C2—C1	121.0 (2)	H8A—C8—H8B	108.1
C3—C2—H2	119.5	N1—C9—C10	111.90 (13)
C1—C2—H2	119.5	N1—C9—H9A	109.2
C2—C3—C4	119.9 (2)	C10—C9—H9A	109.2
C2—C3—H3	120.0	N1—C9—H9B	109.2
C4—C3—H3	120.0	C10—C9—H9B	109.2
C3—C4—C5	120.3 (2)	H9A—C9—H9B	107.9
C3—C4—H4	119.9	O1—C10—N2	122.83 (15)
C5—C4—H4	119.9	O1—C10—C9	123.14 (14)
C4—C5—C6	120.8 (2)	N2—C10—C9	113.99 (13)
C4—C5—H5	119.6	C7—N1—C6	124.21 (13)
C6—C5—H5	119.6	C7—N1—C9	115.53 (14)
C5—C6—C1	118.46 (16)	C6—N1—C9	120.12 (13)
C5—C6—N1	121.03 (15)	C10—N2—N3	122.91 (15)
C1—C6—N1	120.49 (15)	C10—N2—H1N	118.4 (13)
O2—C7—N1	121.60 (17)	N3—N2—H1N	117.0 (14)
O2—C7—C8	120.86 (17)	N2—N3—H2N	105.3 (19)
N1—C7—C8	117.53 (15)	N2—N3—H3N	105.6 (16)
C7—C8—S1	110.54 (14)	H2N—N3—H3N	112 (2)
C7—C8—H8A	109.5	C1—S1—C8	95.78 (9)

C6—C1—C2—C3	1.6 (3)	O2—C7—N1—C6	−178.88 (18)
S1—C1—C2—C3	−177.5 (2)	C8—C7—N1—C6	−0.2 (2)
C1—C2—C3—C4	−0.8 (4)	O2—C7—N1—C9	−3.3 (2)
C2—C3—C4—C5	−0.7 (4)	C8—C7—N1—C9	175.45 (16)
C3—C4—C5—C6	1.2 (3)	C5—C6—N1—C7	155.73 (17)
C4—C5—C6—C1	−0.3 (3)	C1—C6—N1—C7	−25.7 (2)
C4—C5—C6—N1	178.29 (17)	C5—C6—N1—C9	−19.7 (2)
C2—C1—C6—C5	−1.1 (3)	C1—C6—N1—C9	158.89 (15)
S1—C1—C6—C5	178.02 (14)	C10—C9—N1—C7	−76.87 (18)
C2—C1—C6—N1	−179.71 (19)	C10—C9—N1—C6	98.95 (17)
S1—C1—C6—N1	−0.6 (2)	O1—C10—N2—N3	4.2 (3)
O2—C7—C8—S1	−135.26 (18)	C9—C10—N2—N3	−178.15 (17)
N1—C7—C8—S1	46.0 (2)	C2—C1—S1—C8	−143.10 (19)
N1—C9—C10—O1	−26.9 (2)	C6—C1—S1—C8	37.80 (16)
N1—C9—C10—N2	155.47 (14)	C7—C8—S1—C1	−58.15 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2ⁱ	0.96 (3)	2.35 (3)	3.299 (3)	171 (2)
N2—H1N···O1ⁱⁱ	0.87 (2)	2.07 (2)	2.935 (2)	175.5 (18)
C3—H3···O2ⁱⁱⁱ	0.93	2.48	3.406 (3)	174
C8—H8B···O1^iv	0.97	2.57	3.442 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O2ⁱ	0.96 (3)	2.35 (3)	3.299 (3)	171 (2)
N2—H1N⋯O1ⁱⁱ	0.87 (2)	2.07 (2)	2.935 (2)	175.5 (18)
C3—H3⋯O2ⁱⁱⁱ	0.93	2.48	3.406 (3)	174
C8—H8B⋯O1^iv	0.97	2.57	3.442 (2)	150

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

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