(E)-N'-[4-(Methyl-sulfan-yl)benzyl-idene]furan-2-carbohydrazide monohydrate.

In the title compound, C(13)H(12)N(2)O(2)S·H(2)O, the dihedral angle between the aromatic rings is 35.34 (19)° and an intra-molecular N-H⋯O hydrogen bond generates an S(5) ring. In the crystal, mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds, generating (001) sheets.

Related literature

For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C13H12N2O2S·H2O

M = 278.32

Monoclinic,

a = 4.7065 (9) Å

b = 12.142 (2) Å

c = 23.979 (5) Å

β = 91.96 (3)°

V = 1369.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

10766 measured reflections

2536 independent reflections

1095 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.172

S = 0.81

2536 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028655/hb5554sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028655/hb5554Isup2.hkl

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

C13H14N2O3S	F(000) = 584
Mr = 278.32	Dx = 1.350 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1095 reflections
a = 4.7065 (9) Å	θ = 3.1–25.5°
b = 12.142 (2) Å	µ = 0.24 mm−1
c = 23.979 (5) Å	T = 293 K
β = 91.96 (3)°	Block, colorless
V = 1369.6 (5) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1095 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.093
graphite	θmax = 25.5°, θmin = 3.1°
phi and ω scans	h = −5→5
10766 measured reflections	k = −14→14
2536 independent reflections	l = −27→29

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2536 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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
C5	0.1858 (6)	0.6495 (3)	0.26977 (12)	0.0476 (8)
N2	0.5006 (6)	0.6551 (2)	0.19538 (11)	0.0543 (7)
C4	−0.0079 (6)	0.5827 (3)	0.30142 (12)	0.0469 (8)
O2	−0.0668 (5)	0.47801 (18)	0.28399 (9)	0.0576 (7)
C6	0.6577 (7)	0.5956 (3)	0.16494 (13)	0.0544 (9)
H6A	0.6664	0.5200	0.1709	0.065*
C1	−0.3067 (8)	0.5097 (3)	0.35996 (15)	0.0695 (11)
H1A	−0.4258	0.5003	0.3898	0.083*
C2	−0.2512 (7)	0.4347 (3)	0.32055 (14)	0.0647 (10)
H2B	−0.3273	0.3641	0.3186	0.078*
C8	1.0074 (7)	0.5792 (3)	0.09165 (14)	0.0686 (11)
H8A	1.0343	0.5060	0.1020	0.082*
C3	−0.1508 (8)	0.6049 (3)	0.34769 (14)	0.0620 (10)
H3A	−0.1473	0.6705	0.3677	0.074*
O1	0.2107 (5)	0.7491 (2)	0.27923 (10)	0.0628 (7)
C7	0.8238 (7)	0.6447 (3)	0.12095 (12)	0.0541 (9)
N1	0.3328 (5)	0.5959 (2)	0.23110 (10)	0.0512 (7)
H1B	0.3227	0.5254	0.2285	0.061*
C12	0.7927 (8)	0.7535 (3)	0.10515 (17)	0.0740 (11)
H12A	0.6732	0.7994	0.1247	0.089*
C11	0.9370 (9)	0.7947 (4)	0.06065 (17)	0.0823 (12)
H11A	0.9137	0.8682	0.0507	0.099*
C10	1.1155 (8)	0.7288 (4)	0.03055 (16)	0.0765 (12)
C9	1.1526 (8)	0.6220 (4)	0.04680 (16)	0.0809 (13)
H9A	1.2764	0.5771	0.0277	0.097*
O3	0.7049 (8)	0.8706 (2)	0.30372 (13)	0.0682 (8)
S1	1.2735 (3)	0.79024 (15)	−0.02691 (5)	0.1234 (7)
C13	1.4598 (13)	0.6810 (6)	−0.0588 (2)	0.161 (3)
H13A	1.5531	0.7084	−0.0910	0.241*
H13B	1.3280	0.6242	−0.0700	0.241*
H13C	1.5989	0.6515	−0.0327	0.241*
H3B	0.857 (12)	0.841 (4)	0.2908 (19)	0.12 (2)*
H3C	0.602 (17)	0.833 (7)	0.288 (3)	0.21 (4)*

	U11	U22	U33	U12	U13	U23
C5	0.0404 (18)	0.047 (2)	0.056 (2)	0.0052 (17)	0.0024 (15)	0.0034 (17)
N2	0.0518 (16)	0.0511 (18)	0.0606 (17)	−0.0064 (15)	0.0103 (14)	0.0021 (14)
C4	0.0471 (18)	0.041 (2)	0.0529 (18)	0.0025 (16)	0.0030 (15)	−0.0020 (15)
O2	0.0659 (14)	0.0447 (14)	0.0631 (14)	−0.0051 (12)	0.0166 (12)	−0.0027 (11)
C6	0.0518 (19)	0.052 (2)	0.059 (2)	−0.0016 (17)	0.0055 (17)	−0.0022 (17)
C1	0.082 (3)	0.063 (3)	0.065 (2)	0.002 (2)	0.023 (2)	0.007 (2)
C2	0.077 (3)	0.053 (2)	0.065 (2)	−0.011 (2)	0.021 (2)	0.0118 (19)
C8	0.060 (2)	0.080 (3)	0.066 (2)	−0.004 (2)	0.0084 (19)	−0.004 (2)
C3	0.069 (2)	0.055 (2)	0.062 (2)	0.0013 (19)	0.0133 (19)	−0.0036 (18)
O1	0.0614 (15)	0.0406 (15)	0.0878 (17)	−0.0035 (12)	0.0195 (13)	−0.0062 (12)
C7	0.0426 (18)	0.065 (3)	0.055 (2)	−0.0044 (18)	−0.0002 (16)	−0.0022 (18)
N1	0.0509 (16)	0.0406 (17)	0.0628 (16)	−0.0010 (13)	0.0091 (14)	0.0006 (13)
C12	0.073 (3)	0.066 (3)	0.083 (3)	−0.001 (2)	0.019 (2)	0.004 (2)
C11	0.083 (3)	0.076 (3)	0.089 (3)	−0.011 (2)	0.012 (2)	0.020 (2)
C10	0.059 (2)	0.109 (4)	0.061 (2)	−0.019 (3)	0.0024 (19)	0.009 (2)
C9	0.067 (3)	0.109 (4)	0.067 (3)	−0.004 (3)	0.017 (2)	−0.005 (3)
O3	0.0683 (18)	0.0448 (17)	0.0929 (19)	−0.0012 (15)	0.0231 (17)	−0.0016 (14)
S1	0.1001 (10)	0.1929 (17)	0.0779 (8)	−0.0324 (10)	0.0135 (7)	0.0432 (9)
C13	0.158 (5)	0.237 (8)	0.092 (4)	−0.087 (5)	0.068 (4)	−0.047 (4)

C5—O1	1.235 (4)	C3—H3A	0.9300
C5—N1	1.344 (4)	C7—C12	1.380 (5)
C5—C4	1.454 (4)	N1—H1B	0.8600
N2—C6	1.280 (4)	C12—C11	1.378 (5)
N2—N1	1.385 (3)	C12—H12A	0.9300
C4—C3	1.344 (4)	C11—C10	1.381 (6)
C4—O2	1.364 (4)	C11—H11A	0.9300
O2—C2	1.360 (4)	C10—C9	1.364 (6)
C6—C7	1.461 (4)	C10—S1	1.754 (4)
C6—H6A	0.9300	C9—H9A	0.9300
C1—C2	1.344 (5)	O3—H3B	0.87 (5)
C1—C3	1.406 (5)	O3—H3C	0.75 (8)
C1—H1A	0.9300	S1—C13	1.777 (6)
C2—H2B	0.9300	C13—H13A	0.9600
C8—C7	1.384 (4)	C13—H13B	0.9600
C8—C9	1.394 (5)	C13—H13C	0.9600
C8—H8A	0.9300
O1—C5—N1	123.6 (3)	C8—C7—C6	119.4 (3)
O1—C5—C4	120.5 (3)	C5—N1—N2	119.6 (3)
N1—C5—C4	115.9 (3)	C5—N1—H1B	120.2
C6—N2—N1	114.4 (3)	N2—N1—H1B	120.2
C3—C4—O2	109.7 (3)	C11—C12—C7	120.6 (4)
C3—C4—C5	131.2 (3)	C11—C12—H12A	119.7
O2—C4—C5	119.0 (3)	C7—C12—H12A	119.7
C2—O2—C4	106.9 (2)	C12—C11—C10	121.3 (4)
N2—C6—C7	121.0 (3)	C12—C11—H11A	119.4
N2—C6—H6A	119.5	C10—C11—H11A	119.4
C7—C6—H6A	119.5	C9—C10—C11	118.4 (4)
C2—C1—C3	107.1 (3)	C9—C10—S1	125.1 (4)
C2—C1—H1A	126.4	C11—C10—S1	116.5 (4)
C3—C1—H1A	126.4	C10—C9—C8	120.9 (4)
C1—C2—O2	109.6 (3)	C10—C9—H9A	119.6
C1—C2—H2B	125.2	C8—C9—H9A	119.6
O2—C2—H2B	125.2	H3B—O3—H3C	96 (6)
C7—C8—C9	120.6 (4)	C10—S1—C13	104.4 (3)
C7—C8—H8A	119.7	S1—C13—H13A	109.5
C9—C8—H8A	119.7	S1—C13—H13B	109.5
C4—C3—C1	106.7 (3)	H13A—C13—H13B	109.5
C4—C3—H3A	126.7	S1—C13—H13C	109.5
C1—C3—H3A	126.7	H13A—C13—H13C	109.5
C12—C7—C8	118.2 (3)	H13B—C13—H13C	109.5
C12—C7—C6	122.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.86	2.37	2.713 (3)	104
N1—H1B···O3i	0.86	2.03	2.864 (4)	162
O3—H3B···O1ii	0.87 (5)	2.03 (6)	2.878 (4)	165 (4)
O3—H3C···O1	0.76 (8)	2.11 (8)	2.800 (4)	152 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2	0.86	2.37	2.713 (3)	104
N1—H1B⋯O3i	0.86	2.03	2.864 (4)	162
O3—H3B⋯O1ii	0.87 (5)	2.03 (6)	2.878 (4)	165 (4)
O3—H3C⋯O1	0.76 (8)	2.11 (8)	2.800 (4)	152 (8)

Symmetry codes: (i) ; (ii) .