N′-(4-Cyano­benzyl­idene)furan-2-carbohydrazide monohydrate

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

doi:10.1107/S1600536810022221

organic compounds

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Volume 66| Part 7| July 2010| Page o1670

doi:10.1107/S1600536810022221

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N′-(4-Cyanobenzylidene)furan-2-carbohydrazide monohydrate

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

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

(Received 7 June 2010; accepted 10 June 2010; online 16 June 2010)

In the title compound, C₁₃H₉N₃O₂·H₂O, the dihedral angle between the aromatic rings is 10.7 (4)° and an intramolecular N—H⋯O hydrogen bond occurs. In the crystal, the components are linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For a related structure and background references, see: Li et al. (2010 ).

Experimental

Crystal data

C₁₃H₉N₃O₂·H₂O
M_r = 257.25
Monoclinic, P 2₁ /n
a = 7.0501 (14) Å
b = 14.295 (3) Å
c = 12.640 (3) Å
β = 103.38 (3)°
V = 1239.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
11389 measured reflections
2834 independent reflections
1568 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.135
S = 0.98
2834 reflections
180 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	2.33	2.692 (2)	106
N1—H1A⋯O3	0.86	2.07	2.920 (2)	169
O3—H3B⋯N3ⁱ	1.00 (4)	1.99 (4)	2.980 (2)	172 (3)
O3—H3C⋯O2ⁱⁱ	0.88 (3)	1.98 (3)	2.848 (2)	171 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: 10.1107/S1600536810022221/hb5490sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022221/hb5490Isup2.hkl

checkCIF report

Related literature top

For a related structure and background references, see: Li et al. (2010).

Experimental top

A mixture of 4-formylbenzonitrile (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 (I) were obtained by recrystallization from ethanol at room temperature.

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.

N'-(4-Cyanobenzylidene)furan-2-carbohydrazide monohydrate top

Crystal data top

C₁₃H₉N₃O₂·H₂O	F(000) = 536
M_r = 257.25	D_x = 1.379 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1568 reflections
a = 7.0501 (14) Å	θ = 2.7–25.5°
b = 14.295 (3) Å	µ = 0.10 mm⁻¹
c = 12.640 (3) Å	T = 293 K
β = 103.38 (3)°	Block, colorless
V = 1239.3 (4) Å³	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1568 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
ϕ and ω scans	h = −8→9
11389 measured reflections	k = −18→18
2834 independent reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0694P)²] where P = (F_o² + 2F_c²)/3
2834 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₃H₉N₃O₂·H₂O	V = 1239.3 (4) Å³
M_r = 257.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.0501 (14) Å	µ = 0.10 mm⁻¹
b = 14.295 (3) Å	T = 293 K
c = 12.640 (3) Å	0.22 × 0.20 × 0.18 mm
β = 103.38 (3)°

Data collection top

Bruker SMART CCD diffractometer	1568 reflections with I > 2σ(I)
11389 measured reflections	R_int = 0.043
2834 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.24 e Å⁻³
2834 reflections	Δρ_min = −0.16 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
N2	0.2572 (2)	0.42473 (10)	0.51829 (12)	0.0431 (4)
N1	0.2142 (2)	0.34390 (9)	0.45997 (12)	0.0440 (4)
H1A	0.1704	0.3458	0.3906	0.053*
O1	0.10154 (18)	0.19128 (9)	0.33670 (10)	0.0526 (4)
C6	0.2239 (3)	0.50009 (12)	0.46228 (15)	0.0461 (5)
H6A	0.1747	0.4964	0.3875	0.055*
C4	0.1844 (3)	0.17816 (13)	0.44486 (15)	0.0442 (5)
O3	0.0883 (2)	0.37589 (11)	0.22607 (12)	0.0654 (5)
C13	0.3865 (3)	0.85907 (14)	0.65549 (17)	0.0548 (5)
O2	0.3075 (2)	0.25365 (9)	0.61179 (11)	0.0595 (4)
C12	0.3138 (3)	0.60216 (13)	0.62661 (16)	0.0525 (5)
H12A	0.3218	0.5497	0.6709	0.063*
C7	0.2620 (3)	0.59186 (12)	0.51417 (15)	0.0420 (4)
C5	0.2414 (3)	0.26093 (12)	0.51272 (15)	0.0436 (4)
C8	0.2453 (3)	0.67132 (13)	0.44979 (16)	0.0518 (5)
H8A	0.2069	0.6655	0.3746	0.062*
C11	0.3534 (3)	0.68908 (13)	0.67294 (16)	0.0551 (5)
H11A	0.3887	0.6952	0.7482	0.066*
C10	0.3405 (3)	0.76786 (12)	0.60708 (16)	0.0453 (5)
C2	0.0589 (3)	0.10477 (13)	0.29261 (18)	0.0566 (6)
H2B	0.0003	0.0931	0.2200	0.068*
N3	0.4234 (3)	0.93164 (12)	0.69148 (17)	0.0721 (6)
C1	0.1133 (3)	0.03943 (15)	0.36854 (18)	0.0654 (6)
H1B	0.1006	−0.0249	0.3588	0.078*
C9	0.2850 (3)	0.75903 (13)	0.49571 (16)	0.0521 (5)
H9A	0.2741	0.8118	0.4516	0.062*
C3	0.1943 (3)	0.08674 (13)	0.46686 (18)	0.0617 (6)
H3A	0.2449	0.0593	0.5342	0.074*
H3B	0.025 (5)	0.438 (3)	0.208 (3)	0.156 (14)*
H3C	−0.005 (4)	0.337 (2)	0.197 (3)	0.120 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0504 (9)	0.0360 (8)	0.0404 (9)	0.0034 (7)	0.0056 (7)	−0.0056 (7)
N1	0.0572 (9)	0.0360 (8)	0.0346 (9)	0.0018 (7)	0.0023 (7)	−0.0016 (6)
O1	0.0708 (9)	0.0435 (7)	0.0389 (8)	−0.0040 (7)	0.0030 (6)	0.0018 (6)
C6	0.0560 (11)	0.0405 (10)	0.0384 (11)	0.0028 (9)	0.0037 (8)	−0.0023 (8)
C4	0.0466 (10)	0.0473 (11)	0.0366 (11)	0.0005 (9)	0.0052 (8)	0.0017 (8)
O3	0.0897 (11)	0.0468 (9)	0.0497 (9)	−0.0047 (9)	−0.0044 (8)	0.0021 (7)
C13	0.0600 (12)	0.0438 (11)	0.0576 (13)	0.0031 (10)	0.0073 (10)	−0.0013 (10)
O2	0.0829 (10)	0.0532 (8)	0.0369 (8)	0.0059 (7)	0.0026 (7)	0.0064 (6)
C12	0.0739 (14)	0.0408 (10)	0.0418 (11)	0.0062 (10)	0.0114 (10)	0.0024 (8)
C7	0.0435 (10)	0.0381 (10)	0.0428 (11)	0.0050 (8)	0.0072 (8)	−0.0002 (8)
C5	0.0451 (10)	0.0468 (11)	0.0377 (11)	0.0064 (9)	0.0074 (8)	0.0064 (8)
C8	0.0653 (12)	0.0467 (11)	0.0392 (12)	0.0028 (9)	0.0038 (9)	−0.0003 (8)
C11	0.0768 (14)	0.0483 (11)	0.0369 (11)	0.0042 (10)	0.0064 (10)	−0.0036 (9)
C10	0.0469 (10)	0.0383 (10)	0.0490 (12)	0.0020 (8)	0.0077 (8)	−0.0048 (8)
C2	0.0708 (14)	0.0460 (11)	0.0488 (12)	−0.0087 (10)	0.0052 (10)	−0.0062 (9)
N3	0.0868 (14)	0.0448 (11)	0.0786 (14)	−0.0037 (10)	0.0064 (11)	−0.0129 (9)
C1	0.0812 (15)	0.0401 (11)	0.0656 (15)	−0.0037 (11)	−0.0021 (12)	−0.0018 (10)
C9	0.0625 (12)	0.0396 (10)	0.0513 (13)	0.0008 (9)	0.0075 (10)	0.0067 (9)
C3	0.0757 (14)	0.0430 (11)	0.0575 (14)	0.0020 (10)	−0.0030 (11)	0.0125 (9)

Geometric parameters (Å, º) top

N2—C6	1.281 (2)	C12—C11	1.374 (3)
N2—N1	1.3664 (18)	C12—C7	1.391 (3)
N1—C5	1.352 (2)	C12—H12A	0.9300
N1—H1A	0.8600	C7—C8	1.386 (2)
O1—C2	1.361 (2)	C8—C9	1.383 (2)
O1—C4	1.370 (2)	C8—H8A	0.9300
C6—C7	1.464 (2)	C11—C10	1.391 (3)
C6—H6A	0.9300	C11—H11A	0.9300
C4—C3	1.335 (2)	C10—C9	1.377 (3)
C4—C5	1.462 (2)	C2—C1	1.331 (3)
O3—H3B	1.00 (4)	C2—H2B	0.9300
O3—H3C	0.87 (3)	C1—C3	1.414 (3)
C13—N3	1.139 (2)	C1—H1B	0.9300
C13—C10	1.445 (3)	C9—H9A	0.9300
O2—C5	1.235 (2)	C3—H3A	0.9300

C6—N2—N1	115.07 (15)	C9—C8—C7	121.00 (18)
C5—N1—N2	119.16 (15)	C9—C8—H8A	119.5
C5—N1—H1A	120.4	C7—C8—H8A	119.5
N2—N1—H1A	120.4	C12—C11—C10	119.89 (18)
C2—O1—C4	106.68 (15)	C12—C11—H11A	120.1
N2—C6—C7	121.01 (17)	C10—C11—H11A	120.1
N2—C6—H6A	119.5	C9—C10—C11	120.09 (17)
C7—C6—H6A	119.5	C9—C10—C13	119.90 (17)
C3—C4—O1	109.38 (16)	C11—C10—C13	120.01 (18)
C3—C4—C5	132.55 (18)	C1—C2—O1	110.06 (19)
O1—C4—C5	118.07 (15)	C1—C2—H2B	125.0
H3B—O3—H3C	102 (3)	O1—C2—H2B	125.0
N3—C13—C10	178.5 (2)	C2—C1—C3	106.77 (19)
C11—C12—C7	120.69 (17)	C2—C1—H1B	126.6
C11—C12—H12A	119.7	C3—C1—H1B	126.6
C7—C12—H12A	119.7	C10—C9—C8	119.63 (17)
C8—C7—C12	118.66 (16)	C10—C9—H9A	120.2
C8—C7—C6	119.31 (17)	C8—C9—H9A	120.2
C12—C7—C6	122.03 (16)	C4—C3—C1	107.11 (19)
O2—C5—N1	123.42 (16)	C4—C3—H3A	126.4
O2—C5—C4	120.96 (16)	C1—C3—H3A	126.4
N1—C5—C4	115.60 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.33	2.692 (2)	106
N1—H1A···O3	0.86	2.07	2.920 (2)	169
O3—H3B···N3ⁱ	1.00 (4)	1.99 (4)	2.980 (2)	172 (3)
O3—H3C···O2ⁱⁱ	0.88 (3)	1.98 (3)	2.848 (2)	171 (3)

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉N₃O₂·H₂O
M_r	257.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.0501 (14), 14.295 (3), 12.640 (3)
β (°)	103.38 (3)
V (Å³)	1239.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11389, 2834, 1568
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.135, 0.98
No. of reflections	2834
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)	0.24, −0.16

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—H1A···O1	0.86	2.33	2.692 (2)	106
N1—H1A···O3	0.86	2.07	2.920 (2)	169
O3—H3B···N3ⁱ	1.00 (4)	1.99 (4)	2.980 (2)	172 (3)
O3—H3C···O2ⁱⁱ	0.88 (3)	1.98 (3)	2.848 (2)	171 (3)

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+1/2, z−1/2.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F., Zhang, F.-G. & Jian, F.-F. (2010). Acta Cryst. E66, o1471. 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
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1670

doi:10.1107/S1600536810022221

Open

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