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

Jiang, J.-H.

doi:10.1107/S1600536810005532

organic compounds

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Volume 66| Part 3| March 2010| Page o627

doi:10.1107/S1600536810005532

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

Jin-He Jiang ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: weifangjjh@126.com

(Received 21 January 2010; accepted 10 February 2010; online 13 February 2010)

In the title compound, C₁₂H₉ClN₂O₂·H₂O, the dihedral angle between the aromatic rings is 13.9 (2)° and an intramolecular N—H⋯O hydrogen bond occurs. In the crystal structure, the components are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For background to Schiff bases, see: Cimerman et al. (1997 ). For a related structure, see: Girgis (2006 ).

Experimental

Crystal data

C₁₂H₉ClN₂O₂·H₂O
M_r = 266.68
Monoclinic, P 2₁
a = 4.5480 (9) Å
b = 12.423 (3) Å
c = 10.971 (2) Å
β = 91.90 (3)°
V = 619.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
5979 measured reflections
2799 independent reflections
1708 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.145
S = 1.04
2799 reflections
171 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack (1983 ), 1319 Friedel pairs
Flack parameter: 0.01 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1ⁱ	0.97 (5)	1.90 (5)	2.865 (4)	174 (5)
O1W—H2W⋯O1ⁱⁱ	0.92 (6)	1.97 (6)	2.873 (4)	168 (5)
N1—H1A⋯O2	0.86	2.36	2.715 (4)	106
N1—H1A⋯O1W	0.86	2.05	2.886 (4)	165
C8—H8A⋯O1W	0.93	2.49	3.290 (5)	144
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+2]$ ; (ii) $[-x-1, y-{\script{1\over 2}}, -z+2]$ .

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/S1600536810005532/hb5316sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005532/hb5316Isup2.hkl

checkCIF report

Comment top

Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound (I), and describe its structure here.

The molcular structure of (I) is shown in Fig. 1. The C7—N1 bond length of 1.342 (4)Å is longer than the C—N double bond [1.281 (2) Å] reported (Girgis, 2006). In the crystal structure, molecules are linked by intermolecular N—H···O hydrogen bonds.

Related literature top

For background to Schiff bases, see: Cimerman et al. (1997). For a related structure, see: Girgis (2006).

Experimental top

A mixture of furan-2-carbohydrazide (0.1 mol), and 4-chlorobenzaldehyde (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.087 mol, yield 87%). 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 (I) showing 30% probability displacement ellipsoids.

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

Crystal data top

C₁₂H₉ClN₂O₂·H₂O	F(000) = 276
M_r = 266.68	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2022 reflections
a = 4.5480 (9) Å	θ = 3.3–27.3°
b = 12.423 (3) Å	µ = 0.31 mm⁻¹
c = 10.971 (2) Å	T = 293 K
β = 91.90 (3)°	Block, colourless
V = 619.5 (2) Å³	0.25 × 0.20 × 0.18 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	1708 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −5→5
5979 measured reflections	k = −16→16
2799 independent reflections	l = −14→14

Refinement top

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0702P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2799 reflections	Δρ_max = 0.23 e Å⁻³
171 parameters	Δρ_min = −0.34 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1319 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (11)

Crystal data top

C₁₂H₉ClN₂O₂·H₂O	V = 619.5 (2) Å³
M_r = 266.68	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.5480 (9) Å	µ = 0.31 mm⁻¹
b = 12.423 (3) Å	T = 293 K
c = 10.971 (2) Å	0.25 × 0.20 × 0.18 mm
β = 91.90 (3)°

Data collection top

Bruker SMART CCD diffractometer	1708 reflections with I > 2σ(I)
5979 measured reflections	R_int = 0.042
2799 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.145	Δρ_max = 0.23 e Å⁻³
S = 1.04	Δρ_min = −0.34 e Å⁻³
2799 reflections	Absolute structure: Flack (1983), 1319 Friedel pairs
171 parameters	Absolute structure parameter: 0.01 (11)
1 restraint

Special details top

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 > 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
Cl1	0.8615 (3)	0.97667 (10)	0.39621 (9)	0.0713 (4)
O1	−0.3072 (6)	0.94704 (18)	1.0474 (2)	0.0525 (6)
O2	−0.5944 (6)	0.68010 (17)	1.0623 (2)	0.0457 (6)
N1	−0.1934 (6)	0.7961 (2)	0.9399 (2)	0.0412 (6)
H1A	−0.2136	0.7276	0.9323	0.049*
N2	−0.0118 (6)	0.8522 (2)	0.8633 (2)	0.0428 (7)
C1	0.6164 (11)	0.8151 (4)	0.5209 (4)	0.0677 (12)
H1B	0.7036	0.7692	0.4657	0.081*
C2	0.6554 (8)	0.9240 (3)	0.5124 (3)	0.0527 (10)
C3	0.5303 (9)	0.9909 (3)	0.5956 (3)	0.0568 (9)
H3A	0.5619	1.0647	0.5907	0.068*
C4	0.3591 (9)	0.9509 (3)	0.6861 (3)	0.0544 (10)
H4A	0.2762	0.9975	0.7417	0.065*
C5	0.3098 (8)	0.8405 (3)	0.6946 (3)	0.0466 (8)
C6	0.4448 (10)	0.7733 (3)	0.6129 (4)	0.0616 (11)
H6A	0.4209	0.6992	0.6193	0.074*
C7	−0.3375 (7)	0.8492 (3)	1.0262 (3)	0.0409 (7)
C8	0.1202 (8)	0.7935 (3)	0.7861 (3)	0.0466 (8)
H8A	0.0950	0.7192	0.7881	0.056*
C9	−0.5355 (7)	0.7844 (3)	1.0984 (3)	0.0398 (7)
C10	−0.6880 (9)	0.8080 (3)	1.1980 (3)	0.0483 (9)
H10A	−0.6893	0.8733	1.2393	0.058*
C11	−0.8474 (9)	0.7132 (3)	1.2281 (3)	0.0515 (9)
H11A	−0.9722	0.7044	1.2928	0.062*
C12	−0.7811 (9)	0.6394 (3)	1.1444 (3)	0.0513 (9)
H12A	−0.8536	0.5694	1.1428	0.062*
O1W	−0.1978 (8)	0.5707 (2)	0.8764 (3)	0.0596 (8)
H1W	−0.037 (11)	0.526 (4)	0.906 (4)	0.084 (15)*
H2W	−0.372 (13)	0.537 (4)	0.893 (4)	0.093 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0710 (7)	0.0849 (8)	0.0595 (5)	−0.0026 (6)	0.0271 (5)	0.0050 (5)
O1	0.0543 (16)	0.0340 (13)	0.0700 (15)	−0.0032 (11)	0.0163 (12)	−0.0029 (12)
O2	0.0529 (15)	0.0354 (12)	0.0497 (13)	−0.0044 (11)	0.0163 (11)	−0.0023 (10)
N1	0.0388 (16)	0.0333 (14)	0.0522 (15)	−0.0034 (12)	0.0113 (12)	0.0006 (13)
N2	0.0353 (15)	0.0413 (15)	0.0521 (16)	−0.0009 (13)	0.0071 (13)	0.0022 (13)
C1	0.081 (3)	0.064 (3)	0.060 (2)	0.003 (2)	0.034 (2)	−0.012 (2)
C2	0.044 (2)	0.064 (3)	0.051 (2)	−0.0025 (18)	0.0087 (16)	−0.0037 (17)
C3	0.065 (2)	0.050 (2)	0.056 (2)	−0.007 (2)	0.0161 (18)	−0.0020 (19)
C4	0.060 (2)	0.048 (2)	0.058 (2)	−0.0010 (18)	0.0225 (18)	−0.0051 (18)
C5	0.042 (2)	0.051 (2)	0.0475 (19)	−0.0007 (17)	0.0098 (15)	−0.0014 (16)
C6	0.072 (3)	0.051 (2)	0.063 (2)	−0.008 (2)	0.025 (2)	−0.0125 (19)
C7	0.0359 (18)	0.0370 (18)	0.0503 (18)	0.0050 (15)	0.0092 (14)	0.0040 (15)
C8	0.044 (2)	0.0413 (18)	0.0550 (19)	−0.0018 (16)	0.0117 (16)	−0.0042 (16)
C9	0.0392 (19)	0.0361 (17)	0.0442 (16)	0.0035 (15)	0.0045 (14)	0.0028 (14)
C10	0.052 (2)	0.045 (2)	0.0493 (18)	0.0023 (16)	0.0125 (16)	−0.0033 (16)
C11	0.054 (2)	0.048 (2)	0.053 (2)	0.0092 (17)	0.0221 (17)	0.0093 (17)
C12	0.059 (2)	0.042 (2)	0.055 (2)	−0.0053 (17)	0.0195 (18)	0.0072 (16)
O1W	0.053 (2)	0.0392 (14)	0.087 (2)	−0.0005 (14)	0.0169 (16)	−0.0001 (14)

Geometric parameters (Å, º) top

Cl1—C2	1.735 (4)	C4—H4A	0.9300
O1—C7	1.244 (4)	C5—C6	1.384 (5)
O2—C12	1.356 (4)	C5—C8	1.466 (5)
O2—C9	1.379 (4)	C6—H6A	0.9300
N1—C7	1.342 (4)	C7—C9	1.461 (5)
N1—N2	1.386 (4)	C8—H8A	0.9300
N1—H1A	0.8600	C9—C10	1.346 (5)
N2—C8	1.282 (4)	C10—C11	1.427 (6)
C1—C2	1.368 (6)	C10—H10A	0.9300
C1—C6	1.396 (6)	C11—C12	1.339 (5)
C1—H1B	0.9300	C11—H11A	0.9300
C2—C3	1.372 (5)	C12—H12A	0.9300
C3—C4	1.375 (5)	O1W—H1W	0.97 (5)
C3—H3A	0.9300	O1W—H2W	0.92 (6)
C4—C5	1.393 (5)

C12—O2—C9	106.2 (3)	C5—C6—H6A	119.5
C7—N1—N2	119.7 (3)	C1—C6—H6A	119.5
C7—N1—H1A	120.1	O1—C7—N1	123.9 (3)
N2—N1—H1A	120.1	O1—C7—C9	120.2 (3)
C8—N2—N1	114.6 (3)	N1—C7—C9	115.8 (3)
C2—C1—C6	119.6 (4)	N2—C8—C5	121.7 (3)
C2—C1—H1B	120.2	N2—C8—H8A	119.2
C6—C1—H1B	120.2	C5—C8—H8A	119.2
C1—C2—C3	119.7 (4)	C10—C9—O2	109.7 (3)
C1—C2—Cl1	119.8 (3)	C10—C9—C7	131.6 (3)
C3—C2—Cl1	120.5 (3)	O2—C9—C7	118.6 (3)
C2—C3—C4	121.3 (4)	C9—C10—C11	106.7 (3)
C2—C3—H3A	119.4	C9—C10—H10A	126.6
C4—C3—H3A	119.4	C11—C10—H10A	126.6
C3—C4—C5	120.0 (4)	C12—C11—C10	106.2 (3)
C3—C4—H4A	120.0	C12—C11—H11A	126.9
C5—C4—H4A	120.0	C10—C11—H11A	126.9
C6—C5—C4	118.4 (4)	C11—C12—O2	111.1 (3)
C6—C5—C8	119.1 (3)	C11—C12—H12A	124.4
C4—C5—C8	122.5 (3)	O2—C12—H12A	124.4
C5—C6—C1	121.0 (4)	H1W—O1W—H2W	109 (5)

C7—N1—N2—C8	178.5 (3)	C6—C5—C8—N2	−179.5 (3)
C6—C1—C2—C3	1.2 (7)	C4—C5—C8—N2	0.2 (6)
C6—C1—C2—Cl1	−178.5 (3)	C12—O2—C9—C10	−1.6 (4)
C1—C2—C3—C4	−1.7 (6)	C12—O2—C9—C7	180.0 (3)
Cl1—C2—C3—C4	178.0 (3)	O1—C7—C9—C10	−6.7 (6)
C2—C3—C4—C5	0.0 (6)	N1—C7—C9—C10	172.3 (4)
C3—C4—C5—C6	2.1 (6)	O1—C7—C9—O2	171.4 (3)
C3—C4—C5—C8	−177.6 (3)	N1—C7—C9—O2	−9.6 (4)
C4—C5—C6—C1	−2.6 (6)	O2—C9—C10—C11	1.1 (4)
C8—C5—C6—C1	177.1 (4)	C7—C9—C10—C11	179.3 (3)
C2—C1—C6—C5	1.0 (7)	C9—C10—C11—C12	−0.3 (4)
N2—N1—C7—O1	−4.2 (5)	C10—C11—C12—O2	−0.7 (4)
N2—N1—C7—C9	176.9 (3)	C9—O2—C12—C11	1.4 (4)
N1—N2—C8—C5	177.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1ⁱ	0.97 (5)	1.90 (5)	2.865 (4)	174 (5)
O1W—H2W···O1ⁱⁱ	0.92 (6)	1.97 (6)	2.873 (4)	168 (5)
N1—H1A···O2	0.86	2.36	2.715 (4)	106
N1—H1A···O1W	0.86	2.05	2.886 (4)	165
C8—H8A···O1W	0.93	2.49	3.290 (5)	144

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉ClN₂O₂·H₂O
M_r	266.68
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	4.5480 (9), 12.423 (3), 10.971 (2)
β (°)	91.90 (3)
V (Å³)	619.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5979, 2799, 1708
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.145, 1.04
No. of reflections	2799
No. of parameters	171
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.34
Absolute structure	Flack (1983), 1319 Friedel pairs
Absolute structure parameter	0.01 (11)

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
O1W—H1W···O1ⁱ	0.97 (5)	1.90 (5)	2.865 (4)	174 (5)
O1W—H2W···O1ⁱⁱ	0.92 (6)	1.97 (6)	2.873 (4)	168 (5)
N1—H1A···O2	0.86	2.36	2.715 (4)	106
N1—H1A···O1W	0.86	2.05	2.886 (4)	165
C8—H8A···O1W	0.93	2.49	3.290 (5)	144

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

References

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Girgis, A. S. (2006). J. Chem. Res. pp. 81–85. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

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doi:10.1107/S1600536810005532

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