(E)-N′-[4-(Methyl­sulfan­yl)benzyl­idene]furan-2-carbohydrazide monohydrate

Li, Y.-F.; Jian, F.-F.

doi:10.1107/S1600536810028655

organic compounds

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Volume 66| Part 8| August 2010| Page o2157

https://doi.org/10.1107/S1600536810028655

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(E)-N′-[4-(Methylsulfanyl)benzylidene]furan-2-carbohydrazide monohydrate

Yu-Feng Li ^a and Fang-Fang Jian ^b ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 14 July 2010; accepted 17 July 2010; online 31 July 2010)

In the title compound, C₁₃H₁₂N₂O₂S·H₂O, the dihedral angle between the aromatic rings is 35.34 (19)° and an intramolecular N—H⋯O hydrogen bond generates an S(5) ring. In the crystal, molecules 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_r = 278.32
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.172
S = 0.81
2536 reflections
180 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 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
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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028655/hb5554Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

A mixture of 4-(methylthio)benzaldehyde (0.1 mol), and furan-2-carbohydrazide (0.1 mol) was stirred in refluxing ethanol (20 ml) for 2 h to afford the title compound (0.090 mol, yield 90%). Colourless blocks of the title compound were obtained by recrystallization from ethanol at room temperature.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids.

(E)-N'-[4-(Methylsulfanyl)benzylidene]furan-2-carbohydrazide monohydrate top

Crystal data top

C₁₃H₁₄N₂O₃S	F(000) = 584
M_r = 278.32	D_x = 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

Data collection top

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

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)] = 0.052	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(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2536 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₃H₁₄N₂O₃S	V = 1369.6 (5) Å³
M_r = 278.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.7065 (9) Å	µ = 0.24 mm⁻¹
b = 12.142 (2) Å	T = 293 K
c = 23.979 (5) Å	0.22 × 0.20 × 0.18 mm
β = 91.96 (3)°

Data collection top

Bruker SMART CCD diffractometer	1095 reflections with I > 2σ(I)
10766 measured reflections	R_int = 0.093
2536 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.18 e Å⁻³
2536 reflections	Δρ_min = −0.25 e Å⁻³
180 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 > 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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂O₃S
M_r	278.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	4.7065 (9), 12.142 (2), 23.979 (5)
β (°)	91.96 (3)
V (Å³)	1369.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10766, 2536, 1095
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.172, 0.81
No. of reflections	2536
No. of parameters	180
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.25

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) x+1, y, z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o2061. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2157

https://doi.org/10.1107/S1600536810028655

Open

access