(2Z,3Z)-3,4-Dihydro-2H-1,4-benzothia­zine-2,3-dione dioxime dihydrate

Kakanejadifard, A.; Amani, V.

doi:10.1107/S1600536808023301

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1628

doi:10.1107/S1600536808023301

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(2Z,3Z)-3,4-Dihydro-2H-1,4-benzothiazine-2,3-dione dioxime dihydrate

Ali Kakanejadifard ^a ^* and Vahid Amani ^b

^aDepartment of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran, and ^bDepartment of Chemistry, Islamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
^*Correspondence e-mail: alikakanejadifard@yahoo.com

(Received 19 July 2008; accepted 23 July 2008; online 31 July 2008)

In the molecule of the title compound, C₈H₁₁N₃O₄S, the thiazine ring adopts an envelope conformation. In the crystal structure, intermolecular N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds link the molecules.

Related literature

For related literature, see: Kakanejadifard, Niknam et al. (2007 ); Kakanejadifard, Saniei et al. (2007 ); Kakanejadifard & Niknam (2006 ); Kakanejadifard & Amani (2008 ). For general background, see: Jones et al. (1961 ); Schrauzer & Kohnle (1964 ); Yari et al. (2006 ); Hashemi et al. (2006 ); Ghiasvand et al. (2004 , 2005 ); Kakanejadifard, Niknam & Zabardasti (2007 ); Gok & Kantekin (1997 ); Hughes (1981 ).

Experimental

Crystal data

C₈H₇N₃O₂S·2H₂O
M_r = 245.26
Orthorhombic, P b c a
a = 9.1636 (18) Å
b = 9.8195 (18) Å
c = 24.165 (4) Å
V = 2174.4 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 120 (2) K
0.5 × 0.5 × 0.1 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.859, T_max = 0.974
15018 measured reflections
2337 independent reflections
1482 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.107
S = 1.02
2337 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯N11ⁱ	0.85	2.11	2.931 (2)	162
O1W—H1WA⋯N13ⁱ	0.85	2.62	3.225 (2)	129
O1W—H1WB⋯O2Wⁱ	0.85	2.00	2.845 (2)	171
O2W—H2WA⋯N13ⁱⁱ	0.85	2.02	2.853 (3)	168
N4—H4⋯O14	0.87	2.08	2.493 (2)	108
O2W—H2WB⋯O1W	0.85	1.94	2.780 (2)	171
O12—H12⋯O2Wⁱⁱⁱ	0.82	1.89	2.699 (2)	171
O14—H14⋯O1W	0.82	1.85	2.673 (2)	179
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023301/hk2502sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023301/hk2502Isup2.hkl

checkCIF report

Comment top

We have been interested in the synthesis and chemical behavior of vic-dioximes, in the past decade. In our investigations, the reaction of amines with dichloroglyoxime or cyanogendi-N-oxide resulted in various symmetrically substituted diaminoglyoxime derivatives, in which some of them were quite suitable to act, as donor species, towards some transition metal ions (Kakanejadifard, Niknam et al., 2007; Kakanejadifard, Saniei et al., 2007; Kakanejadifard & Niknam, 2006; Kakanejadifard & Amani, 2008). Some oximes are widely used for various purposes in organic, inorganic, bioinorganic, pigment, analytical, dyes and medical chemistry (Jones et al., 1961; Schrauzer & Kohnle, 1964; Yari et al., 2006; Hashemi et al., 2006; Ghiasvand et al., 2004; Ghiasvand et al., 2005; Kakanejadifard, Niknam & Zabardasti, 2007). vic-Dioximes, containing mildly acidic hydroxyl groups and slightly basic nitrogen atoms, are amphoteric and their transition metal complexes have been widely investigated as analytical reagents (Gok & Kantekin, 1997), and models for biological systems such as vitamin B₁₂ (Hughes, 1981). We report herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths and angles are within normal ranges. Ring A (S1/N4/C2/C3/C5/C6) adopts envelope conformation, with C2 atom displaced by 0.248 (3) Å from the plane of the other ring atoms. Ring B (C5–C10) is, of course, planar.

In the crystal structure, intermolecular N—H···O, O—H···O and O—H···N hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Kakanejadifard, Niknam et al. (2007); Kakanejadifard, Saniei et al. (2007); Kakanejadifard & Niknam (2006); Kakanejadifard & Amani (2008). For general background, see: Jones et al. (1961); Schrauzer & Kohnle (1964); Yari et al. (2006); Hashemi et al. (2006); Ghiasvand et al. (2004, 2005); Kakanejadifard, Niknam & Zabardasti (2007); Gok & Kantekin (1997); Hughes (1981).

Experimental top

For the preparation of the title compound, a solution of NaHCO₃ (0.05 g, 0.6 mmol) in aqueous EtOH (10 ml) was added to a magnetically stirred solution of dicholoroglyoxime (1.57 g, 10 mmol) in aqueous EtOH (15 ml) and a solution of 2-aminothiophenole (1.25 g, 10 mmol) in EtOH (15 ml) at room temperature. The solution was stirred for 4 h and then the mixture was filtered. The filtrate was placed at room temperature for 24 h. The gray precipitate was removed by filtration and precipitate was washed with cold THF. It was recrystallized from 2-propanol in one week (yield; 0.31 g, 74.2%, m.p. 492 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title molecule. Hydrogen bonds are shown as dashed lines.

(2Z,3Z)-3,4-Dihydro-2H-1,4-benzothiazine-2,3-dione dioxime dihydrate top

Crystal data top

C₈H₇N₃O₂S·2H₂O	F(000) = 1024
M_r = 245.26	D_x = 1.498 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 910 reflections
a = 9.1636 (18) Å	θ = 2.5–26.3°
b = 9.8195 (18) Å	µ = 0.30 mm⁻¹
c = 24.165 (4) Å	T = 120 K
V = 2174.4 (7) Å³	Plate, yellow
Z = 8	0.5 × 0.5 × 0.1 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2337 independent reflections
Radiation source: fine-focus sealed tube	1482 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
T_min = 0.859, T_max = 0.974	k = −12→12
15018 measured reflections	l = −30→28

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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0534P)² + 0.01P] where P = (F_o² + 2F_c²)/3
2337 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₈H₇N₃O₂S·2H₂O	V = 2174.4 (7) Å³
M_r = 245.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.1636 (18) Å	µ = 0.30 mm⁻¹
b = 9.8195 (18) Å	T = 120 K
c = 24.165 (4) Å	0.5 × 0.5 × 0.1 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2337 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	1482 reflections with I > 2σ(I)
T_min = 0.859, T_max = 0.974	R_int = 0.082
15018 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	Δρ_max = 0.43 e Å⁻³
2337 reflections	Δρ_min = −0.25 e Å⁻³
145 parameters

Special details top

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 > 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.

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

	x	y	z	U_iso*/U_eq
S1	0.18557 (6)	0.97098 (6)	0.44569 (2)	0.02751 (18)
O1W	0.74924 (16)	1.21073 (15)	0.24961 (6)	0.0294 (4)
H1WA	0.7567	1.1544	0.2230	0.035*
H1WB	0.8298	1.2523	0.2539	0.035*
O2W	0.50348 (16)	1.37490 (17)	0.23976 (6)	0.0302 (4)
H2WA	0.5201	1.4420	0.2185	0.036*
H2WB	0.5838	1.3317	0.2411	0.036*
O12	0.07401 (16)	0.93917 (17)	0.34431 (6)	0.0326 (4)
H12	0.0423	0.9158	0.3140	0.049*
O14	0.61786 (17)	1.16110 (16)	0.34627 (6)	0.0316 (4)
H14	0.6570	1.1757	0.3163	0.047*
N4	0.4660 (2)	1.14780 (19)	0.43170 (7)	0.0231 (4)
H4	0.5489	1.1895	0.4276	0.022*
N11	0.20659 (19)	1.00628 (19)	0.33728 (8)	0.0268 (5)
N13	0.48394 (19)	1.09374 (19)	0.33772 (8)	0.0236 (4)
C2	0.2680 (2)	1.0265 (2)	0.38436 (9)	0.0223 (5)
C3	0.4132 (2)	1.0922 (2)	0.38433 (9)	0.0211 (5)
C5	0.4075 (2)	1.1389 (2)	0.48497 (9)	0.0212 (5)
C6	0.2847 (2)	1.0617 (2)	0.49653 (9)	0.0228 (5)
C7	0.2320 (2)	1.0540 (2)	0.55071 (9)	0.0269 (5)
H7	0.1500	1.0014	0.5584	0.032*
C8	0.3006 (3)	1.1236 (2)	0.59269 (9)	0.0289 (6)
H8	0.2651	1.1183	0.6287	0.035*
C9	0.4222 (3)	1.2015 (2)	0.58121 (10)	0.0302 (6)
H9	0.4683	1.2493	0.6094	0.036*
C10	0.4756 (3)	1.2084 (2)	0.52783 (9)	0.0269 (6)
H10	0.5583	1.2602	0.5205	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0211 (3)	0.0357 (3)	0.0257 (3)	−0.0062 (3)	0.0008 (2)	0.0020 (3)
O1W	0.0243 (9)	0.0344 (9)	0.0295 (9)	−0.0021 (7)	0.0050 (7)	−0.0041 (8)
O2W	0.0251 (8)	0.0325 (9)	0.0329 (10)	0.0035 (7)	0.0048 (7)	0.0067 (8)
O12	0.0237 (9)	0.0466 (11)	0.0275 (9)	−0.0140 (8)	−0.0027 (7)	−0.0017 (8)
O14	0.0269 (9)	0.0398 (10)	0.0282 (9)	−0.0107 (8)	0.0022 (7)	0.0030 (8)
N4	0.0217 (9)	0.0262 (11)	0.0213 (10)	−0.0026 (8)	0.0009 (8)	−0.0002 (8)
N11	0.0201 (10)	0.0316 (11)	0.0287 (11)	−0.0038 (8)	−0.0016 (8)	0.0025 (9)
N13	0.0209 (10)	0.0249 (10)	0.0251 (10)	−0.0049 (8)	−0.0011 (8)	0.0008 (8)
C2	0.0200 (11)	0.0249 (11)	0.0220 (12)	0.0024 (10)	0.0004 (9)	0.0010 (10)
C3	0.0215 (11)	0.0200 (11)	0.0219 (12)	0.0014 (10)	−0.0025 (9)	0.0018 (10)
C5	0.0220 (11)	0.0198 (11)	0.0218 (12)	0.0067 (10)	0.0003 (9)	0.0017 (10)
C6	0.0210 (12)	0.0239 (12)	0.0236 (13)	0.0061 (9)	−0.0015 (9)	0.0033 (9)
C7	0.0224 (11)	0.0316 (14)	0.0268 (13)	0.0050 (10)	0.0023 (10)	0.0060 (11)
C8	0.0320 (13)	0.0327 (13)	0.0219 (13)	0.0095 (11)	0.0042 (11)	0.0021 (11)
C9	0.0413 (15)	0.0251 (13)	0.0243 (14)	0.0050 (11)	−0.0033 (11)	−0.0024 (10)
C10	0.0310 (13)	0.0209 (12)	0.0289 (14)	0.0006 (10)	−0.0003 (11)	0.0019 (10)

Geometric parameters (Å, º) top

S1—C2	1.750 (2)	C2—C3	1.479 (3)
S1—C6	1.769 (2)	C5—C6	1.385 (3)
S1—C5	2.785 (2)	C5—C10	1.388 (3)
S1—C3	2.823 (2)	C6—C7	1.398 (3)
O12—N11	1.393 (2)	C7—C8	1.376 (3)
O12—H12	0.8200	C7—H7	0.9300
O14—N13	1.409 (2)	C8—C9	1.380 (3)
O14—C3	2.195 (3)	C8—H8	0.9300
O14—H14	0.8200	C9—C10	1.381 (3)
N4—C3	1.357 (3)	C9—H9	0.9300
N4—C5	1.397 (3)	C10—H10	0.9300
N4—H4	0.8691	O1W—H1WA	0.8501
N11—C2	1.285 (3)	O1W—H1WB	0.8499
N11—C3	2.364 (3)	O2W—H2WA	0.8500
N13—C3	1.299 (3)	O2W—H2WB	0.8500

C2—S1—C6	102.11 (11)	C10—C5—S1	150.86 (16)
C2—S1—C5	77.83 (9)	N4—C5—S1	90.18 (13)
C6—S1—C3	76.88 (9)	C9—C5—S1	121.39 (10)
C5—S1—C3	52.39 (6)	C7—C5—S1	62.11 (8)
N11—O12—H12	109.5	C3—C5—S1	64.59 (7)
N13—O14—H14	109.5	C6—C5—C5ⁱ	85.42 (14)
C3—O14—H14	142.8	C10—C5—C5ⁱ	90.62 (14)
C3—N4—C5	127.96 (19)	N4—C5—C5ⁱ	93.28 (14)
C3—N4—H4	113.8	C9—C5—C5ⁱ	88.25 (10)
C5—N4—H4	118.1	C7—C5—C5ⁱ	84.92 (10)
C2—N11—O12	110.30 (18)	C3—C5—C5ⁱ	92.99 (10)
O12—N11—C3	143.99 (15)	S1—C5—C5ⁱ	87.74 (9)
C3—N13—O14	108.23 (17)	C5—C6—C7	120.0 (2)
N11—C2—C3	117.44 (19)	C5—C6—S1	123.56 (17)
N11—C2—S1	120.86 (17)	C7—C6—S1	116.47 (17)
C3—C2—S1	121.64 (16)	C5—C6—C9	60.51 (13)
N13—C3—N4	123.3 (2)	C7—C6—C9	59.46 (14)
N13—C3—C2	117.02 (19)	S1—C6—C9	175.77 (13)
N4—C3—C2	119.71 (19)	C8—C7—C6	120.4 (2)
N4—C3—O14	85.70 (14)	C6—C7—C9	90.21 (16)
C2—C3—O14	154.59 (16)	C8—C7—C5	90.50 (16)
N13—C3—N11	89.24 (14)	C9—C7—C5	60.34 (10)
N4—C3—N11	146.56 (17)	C8—C7—H7	119.8
O14—C3—N11	126.34 (11)	C6—C7—H7	119.8
N13—C3—C5	149.31 (17)	C9—C7—H7	150.0
C2—C3—C5	93.51 (14)	C5—C7—H7	149.7
O14—C3—C5	111.88 (11)	C7—C8—C9	119.8 (2)
N11—C3—C5	121.44 (11)	C7—C8—H8	120.1
N13—C3—S1	145.97 (16)	C9—C8—H8	120.1
N4—C3—S1	89.42 (13)	C8—C9—C10	120.1 (2)
O14—C3—S1	168.89 (11)	C10—C9—C7	90.00 (16)
N11—C3—S1	60.67 (7)	C8—C9—C5	90.44 (16)
C5—C3—S1	63.02 (7)	C7—C9—C5	60.37 (9)
N13—C3—C9ⁱ	90.05 (14)	C8—C9—C6	60.40 (14)
N4—C3—C9ⁱ	88.63 (13)	C10—C9—C6	59.67 (14)
C2—C3—C9ⁱ	91.67 (14)	C8—C9—C3ⁱ	80.63 (14)
O14—C3—C9ⁱ	89.14 (9)	C10—C9—C3ⁱ	96.59 (15)
N11—C3—C9ⁱ	99.92 (10)	C7—C9—C3ⁱ	83.30 (9)
C5—C3—C9ⁱ	85.70 (8)	C5—C9—C3ⁱ	92.62 (9)
S1—C3—C9ⁱ	80.76 (7)	C6—C9—C3ⁱ	87.82 (8)
C6—C5—C10	118.9 (2)	C8—C9—H9	120.0
C6—C5—N4	122.1 (2)	C10—C9—H9	120.0
C10—C5—N4	119.0 (2)	C7—C9—H9	150.0
C6—C5—C9	89.45 (15)	C5—C9—H9	149.6
N4—C5—C9	148.43 (17)	C6—C9—H9	179.4
C10—C5—C7	88.76 (15)	C3ⁱ—C9—H9	92.8
N4—C5—C7	152.27 (17)	C9—C10—C5	120.9 (2)
C9—C5—C7	59.29 (10)	C9—C10—H10	119.5
C6—C5—C3	96.54 (15)	C5—C10—H10	119.5
C10—C5—C3	144.53 (17)	H1WA—O1W—H1WB	109.6
C9—C5—C3	173.96 (13)	H2WA—O2W—H2WB	104.7
C7—C5—C3	126.70 (12)

O12—N11—C2—C3	177.69 (18)	C2—S1—C5—C9	170.77 (13)
O12—N11—C2—S1	0.5 (3)	C6—S1—C5—C9	−1.59 (17)
C3—N11—C2—S1	−177.2 (3)	C3—S1—C5—C9	179.04 (14)
C6—S1—C2—N11	−164.88 (19)	C2—S1—C5—C7	171.89 (11)
C5—S1—C2—N11	−168.1 (2)	C6—S1—C5—C7	−0.47 (18)
C3—S1—C2—N11	177.1 (3)	C3—S1—C5—C7	−179.84 (10)
C6—S1—C2—C3	18.0 (2)	C2—S1—C5—C3	−8.27 (10)
C5—S1—C2—C3	14.80 (18)	C6—S1—C5—C3	179.4 (2)
O14—N13—C3—N4	−0.1 (3)	C2—S1—C5—C5ⁱ	−102.67 (11)
O14—N13—C3—C2	179.59 (18)	C6—S1—C5—C5ⁱ	85.0 (2)
O14—N13—C3—N11	171.56 (13)	C3—S1—C5—C5ⁱ	−94.39 (10)
O14—N13—C3—C5	−6.9 (4)	C10—C5—C6—C7	−0.4 (3)
O14—N13—C3—S1	−161.9 (2)	N4—C5—C6—C7	178.8 (2)
O14—N13—C3—C9ⁱ	−88.52 (14)	C9—C5—C6—C7	−0.5 (2)
C5—N4—C3—N13	−172.2 (2)	C3—C5—C6—C7	−179.75 (18)
C5—N4—C3—C2	8.1 (3)	S1—C5—C6—C7	−179.2 (3)
C5—N4—C3—O14	−172.3 (2)	C5ⁱ—C5—C6—C7	87.8 (2)
C5—N4—C3—N11	23.0 (4)	C10—C5—C6—S1	178.75 (16)
C5—N4—C3—S1	−2.3 (2)	N4—C5—C6—S1	−2.1 (3)
C5—N4—C3—C9ⁱ	−83.1 (2)	C9—C5—C6—S1	178.65 (15)
N11—C2—C3—N13	−16.8 (3)	C7—C5—C6—S1	179.2 (3)
S1—C2—C3—N13	160.36 (17)	C3—C5—C6—S1	−0.57 (19)
N11—C2—C3—N4	162.9 (2)	C5ⁱ—C5—C6—S1	−93.07 (16)
S1—C2—C3—N4	−19.9 (3)	C10—C5—C6—C9	0.10 (16)
N11—C2—C3—O14	−16.2 (5)	N4—C5—C6—C9	179.3 (2)
S1—C2—C3—O14	160.9 (3)	C7—C5—C6—C9	0.5 (2)
S1—C2—C3—N11	177.2 (3)	C3—C5—C6—C9	−179.22 (13)
N11—C2—C3—C5	166.47 (19)	S1—C5—C6—C9	−178.65 (15)
S1—C2—C3—C5	−16.35 (19)	C5ⁱ—C5—C6—C9	88.29 (10)
N11—C2—C3—S1	−177.2 (3)	C2—S1—C6—C5	−7.6 (2)
N11—C2—C3—C9ⁱ	−107.7 (2)	C3—S1—C6—C5	0.51 (17)
S1—C2—C3—C9ⁱ	69.45 (17)	C2—S1—C6—C7	171.56 (17)
N13—O14—C3—N4	179.9 (2)	C5—S1—C6—C7	179.2 (3)
N13—O14—C3—C2	−0.9 (4)	C3—S1—C6—C7	179.71 (18)
N13—O14—C3—N11	−10.50 (17)	C5—C6—C7—C8	0.6 (3)
N13—O14—C3—C5	176.2 (2)	S1—C6—C7—C8	−178.67 (17)
N13—O14—C3—S1	115.7 (6)	C9—C6—C7—C8	0.03 (17)
N13—O14—C3—C9ⁱ	91.21 (18)	C5—C6—C7—C9	0.5 (2)
C2—N11—C3—N13	165.1 (3)	S1—C6—C7—C9	−178.70 (13)
O12—N11—C3—N13	161.4 (2)	S1—C6—C7—C5	−179.2 (3)
C2—N11—C3—N4	−27.6 (3)	C9—C6—C7—C5	−0.5 (2)
O12—N11—C3—N4	−31.3 (4)	C6—C5—C7—C8	−179.5 (3)
O12—N11—C3—C2	−3.7 (3)	C10—C5—C7—C8	0.11 (18)
C2—N11—C3—O14	171.4 (3)	N4—C5—C7—C8	178.2 (3)
O12—N11—C3—O14	167.7 (2)	C9—C5—C7—C8	−0.13 (13)
C2—N11—C3—C5	−15.9 (2)	C3—C5—C7—C8	−179.20 (15)
O12—N11—C3—C5	−19.6 (3)	S1—C5—C7—C8	−179.02 (15)
C2—N11—C3—S1	1.7 (2)	C5ⁱ—C5—C7—C8	90.85 (15)
O12—N11—C3—S1	−2.0 (2)	C10—C5—C7—C6	179.6 (3)
C2—N11—C3—C9ⁱ	75.1 (2)	N4—C5—C7—C6	−2.3 (4)
O12—N11—C3—C9ⁱ	71.4 (3)	C9—C5—C7—C6	179.4 (2)
C2—S1—C3—N13	−32.4 (3)	C3—C5—C7—C6	0.3 (2)
C6—S1—C3—N13	165.8 (3)	S1—C5—C7—C6	0.50 (19)
C5—S1—C3—N13	166.0 (3)	C5ⁱ—C5—C7—C6	−89.6 (2)
C2—S1—C3—N4	162.8 (3)	C6—C5—C7—C9	−179.4 (2)
C6—S1—C3—N4	0.88 (13)	C10—C5—C7—C9	0.24 (13)
C5—S1—C3—N4	1.15 (11)	N4—C5—C7—C9	178.4 (4)
C6—S1—C3—C2	−161.9 (2)	C3—C5—C7—C9	−179.07 (15)
C5—S1—C3—C2	−161.6 (2)	S1—C5—C7—C9	−178.89 (10)
C2—S1—C3—O14	−133.4 (7)	C5ⁱ—C5—C7—C9	90.98 (10)
C6—S1—C3—O14	64.8 (6)	C6—C7—C8—C9	−0.1 (3)
C5—S1—C3—O14	65.0 (6)	C5—C7—C8—C9	0.2 (2)
C2—S1—C3—N11	−1.56 (18)	C7—C8—C9—C10	−0.6 (3)
C6—S1—C3—N11	−163.45 (10)	C7—C8—C9—C5	−0.2 (2)
C5—S1—C3—N11	−163.18 (10)	C7—C8—C9—C6	0.03 (17)
C2—S1—C3—C5	161.6 (2)	C7—C8—C9—C3ⁱ	−92.8 (2)
C6—S1—C3—C5	−0.27 (9)	C6—C7—C9—C8	180.0 (3)
C2—S1—C3—C9ⁱ	−108.5 (2)	C5—C7—C9—C8	−179.7 (3)
C6—S1—C3—C9ⁱ	89.59 (9)	C8—C7—C9—C10	179.5 (3)
C5—S1—C3—C9ⁱ	89.86 (8)	C6—C7—C9—C10	−0.55 (18)
C3—N4—C5—C6	3.4 (3)	C5—C7—C9—C10	−0.24 (13)
C3—N4—C5—C10	−177.4 (2)	C8—C7—C9—C5	179.7 (3)
C3—N4—C5—C9	−177.9 (2)	C6—C7—C9—C5	−0.31 (12)
C3—N4—C5—C7	4.8 (5)	C8—C7—C9—C6	−180.0 (3)
C3—N4—C5—S1	2.3 (2)	C5—C7—C9—C6	0.31 (12)
C3—N4—C5—C5ⁱ	90.1 (2)	C8—C7—C9—C3ⁱ	82.9 (2)
N13—C3—C5—C6	−164.3 (3)	C6—C7—C9—C3ⁱ	−97.18 (14)
N4—C3—C5—C6	−177.1 (3)	C5—C7—C9—C3ⁱ	−96.88 (9)
C2—C3—C5—C6	9.93 (18)	C6—C5—C9—C8	0.44 (18)
O14—C3—C5—C6	−168.81 (14)	C10—C5—C9—C8	−179.4 (3)
N11—C3—C5—C6	17.53 (18)	N4—C5—C9—C8	−178.4 (3)
S1—C3—C5—C6	0.34 (11)	C7—C5—C9—C8	0.13 (13)
C9ⁱ—C3—C5—C6	−81.48 (13)	S1—C5—C9—C8	1.28 (18)
N13—C3—C5—C10	16.7 (5)	C5ⁱ—C5—C9—C8	−85.00 (15)
N4—C3—C5—C10	3.9 (3)	C6—C5—C9—C10	179.8 (3)
C2—C3—C5—C10	−169.0 (3)	N4—C5—C9—C10	1.0 (3)
O14—C3—C5—C10	12.2 (3)	C7—C5—C9—C10	179.5 (3)
N11—C3—C5—C10	−161.4 (2)	S1—C5—C9—C10	−179.3 (3)
S1—C3—C5—C10	−178.6 (3)	C5ⁱ—C5—C9—C10	94.4 (2)
C9ⁱ—C3—C5—C10	99.5 (3)	C6—C5—C9—C7	0.31 (12)
N13—C3—C5—N4	12.8 (3)	C10—C5—C9—C7	−179.5 (3)
C2—C3—C5—N4	−173.0 (3)	N4—C5—C9—C7	−178.5 (3)
O14—C3—C5—N4	8.3 (2)	S1—C5—C9—C7	1.15 (10)
N11—C3—C5—N4	−165.4 (3)	C5ⁱ—C5—C9—C7	−85.13 (10)
S1—C3—C5—N4	177.4 (3)	C10—C5—C9—C6	−179.8 (3)
C9ⁱ—C3—C5—N4	95.6 (2)	N4—C5—C9—C6	−178.8 (4)
N13—C3—C5—C7	−164.5 (3)	C7—C5—C9—C6	−0.31 (12)
N4—C3—C5—C7	−177.2 (3)	S1—C5—C9—C6	0.84 (9)
C2—C3—C5—C7	9.77 (19)	C5ⁱ—C5—C9—C6	−85.44 (14)
O14—C3—C5—C7	−168.97 (12)	C6—C5—C9—C3ⁱ	81.08 (13)
N11—C3—C5—C7	17.37 (19)	C10—C5—C9—C3ⁱ	−98.7 (2)
S1—C3—C5—C7	0.18 (11)	N4—C5—C9—C3ⁱ	−97.8 (3)
C9ⁱ—C3—C5—C7	−81.64 (13)	C7—C5—C9—C3ⁱ	80.77 (9)
N13—C3—C5—S1	−164.6 (3)	S1—C5—C9—C3ⁱ	81.92 (11)
N4—C3—C5—S1	−177.4 (3)	C5ⁱ—C5—C9—C3ⁱ	−4.36 (9)
C2—C3—C5—S1	9.60 (11)	C5—C6—C9—C8	−179.5 (2)
O14—C3—C5—S1	−169.15 (11)	C7—C6—C9—C8	−0.03 (17)
N11—C3—C5—S1	17.20 (10)	C5—C6—C9—C10	−0.11 (16)
C9ⁱ—C3—C5—S1	−81.81 (7)	C7—C6—C9—C10	179.4 (2)
N13—C3—C5—C5ⁱ	−78.6 (3)	C5—C6—C9—C7	−179.5 (2)
N4—C3—C5—C5ⁱ	−91.3 (2)	C7—C6—C9—C5	179.5 (2)
C2—C3—C5—C5ⁱ	95.66 (15)	C5—C6—C9—C3ⁱ	−99.04 (13)
O14—C3—C5—C5ⁱ	−83.09 (12)	C7—C6—C9—C3ⁱ	80.43 (14)
N11—C3—C5—C5ⁱ	103.26 (13)	C8—C9—C10—C5	0.7 (3)
S1—C3—C5—C5ⁱ	86.06 (9)	C7—C9—C10—C5	0.4 (2)
C9ⁱ—C3—C5—C5ⁱ	4.25 (9)	C6—C9—C10—C5	0.11 (16)
C2—S1—C5—C6	172.4 (2)	C3ⁱ—C9—C10—C5	83.7 (2)
C3—S1—C5—C6	−179.4 (2)	C6—C5—C10—C9	−0.2 (3)
C2—S1—C5—C10	170.1 (3)	N4—C5—C10—C9	−179.4 (2)
C6—S1—C5—C10	−2.2 (3)	C7—C5—C10—C9	−0.4 (2)
C3—S1—C5—C10	178.4 (3)	C3—C5—C10—C9	178.6 (2)
C2—S1—C5—N4	−9.39 (13)	S1—C5—C10—C9	1.1 (4)
C6—S1—C5—N4	178.2 (3)	C5ⁱ—C5—C10—C9	−85.3 (2)
C3—S1—C5—N4	−1.12 (11)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N11ⁱⁱ	0.85	2.11	2.931 (2)	162
O1W—H1WA···N13ⁱⁱ	0.85	2.62	3.225 (2)	129
O1W—H1WB···O2Wⁱⁱ	0.85	2.00	2.845 (2)	171
O2W—H2WA···N13ⁱⁱⁱ	0.85	2.02	2.853 (3)	168
N4—H4···O14	0.87	2.08	2.493 (2)	108
O2W—H2WB···O1W	0.85	1.94	2.780 (2)	171
O12—H12···O2W^iv	0.82	1.89	2.699 (2)	171
O14—H14···O1W	0.82	1.85	2.673 (2)	179

Symmetry codes: (ii) x+1/2, y, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₈H₇N₃O₂S·2H₂O
M_r	245.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	9.1636 (18), 9.8195 (18), 24.165 (4)
V (Å³)	2174.4 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.5 × 0.5 × 0.1

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.859, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	15018, 2337, 1482
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.107, 1.02
No. of reflections	2337
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.25

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N11ⁱ	0.85	2.11	2.931 (2)	162
O1W—H1WA···N13ⁱ	0.85	2.62	3.225 (2)	129
O1W—H1WB···O2Wⁱ	0.85	2.00	2.845 (2)	171
O2W—H2WA···N13ⁱⁱ	0.85	2.02	2.853 (3)	168
N4—H4···O14	0.87	2.08	2.493 (2)	108
O2W—H2WB···O1W	0.85	1.94	2.780 (2)	171
O12—H12···O2Wⁱⁱⁱ	0.82	1.89	2.699 (2)	171
O14—H14···O1W	0.82	1.85	2.673 (2)	179

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, z.

Acknowledgements

The authors acknowledge the Research Grant Council of Lorestan University for financial support.

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