N'-(4-Chloro-benzyl-idene)furan-2-carbohydrazide monohydrate.

In the title compound, C(12)H(9)ClN(2)O(2)·H(2)O, the dihedral angle between the aromatic rings is 13.9 (2)° and an intra-molecular 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 = 266.68

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.145

S = 1.04

2799 reflections

171 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 1319 Friedel pairs

Flack parameter: 0.01 (11)

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/S1600536810005532/hb5316sup1.cif

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

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

C12H9ClN2O2·H2O	F(000) = 276
Mr = 266.68	Dx = 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

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

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(Fo2) + (0.0702P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2799 reflections	Δρmax = 0.23 e Å−3
171 parameters	Δρmin = −0.33 e Å−3
1 restraint	Absolute structure: Flack (1983), 1319 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (11)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) .