(E)-N'-(4-Chloro-benzyl-idene)-1-benzofuran-2-carbohydrazide monohydrate.

The title compound, C(16)H(11)ClN(2)O(2)·H(2)O, exists in an E conformation with respect to the N=C bond. The benzofuran ring system forms a dihedral angle of 1.26 (4)° with the benzene ring. In the crystal, mol-ecules are linked via (N,C)-H⋯O bifurcated acceptor hydrogen bonds and (O,O,C)-H⋯O trifurcated acceptor hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For general background to hydrazone derivatives, see: Sridhar & Perumal (2003 ▶); Vijayakumar et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For related structures, see: Fun, Quah & Abdel-Aziz (2012 ▶); Fun, Quah, Nitinchandra et al. (2012 ▶); Fun, Quah, Shyma et al. (2012 ▶).

Experimental

Crystal data

C16H11ClN2O2·H2O

M = 316.73

Monoclinic,

a = 24.6121 (15) Å

b = 4.6625 (3) Å

c = 12.6570 (8) Å

β = 99.294 (1)°

V = 1433.37 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.57 × 0.34 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.856, T max = 0.975

7338 measured reflections

4620 independent reflections

4511 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.04

4620 reflections

211 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 2025 Friedel pairs

Flack parameter: 0.03 (3)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027523/is5157sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027523/is5157Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027523/is5157Isup3.cml

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

C16H11ClN2O2·H2O	F(000) = 656
Mr = 316.73	Dx = 1.468 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5261 reflections
a = 24.6121 (15) Å	θ = 3.3–32.6°
b = 4.6625 (3) Å	µ = 0.28 mm−1
c = 12.6570 (8) Å	T = 100 K
β = 99.294 (1)°	Plate, yellow
V = 1433.37 (16) Å3	0.57 × 0.34 × 0.09 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	4620 independent reflections
Radiation source: fine-focus sealed tube	4511 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 32.6°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −35→36
Tmin = 0.856, Tmax = 0.975	k = −6→7
7338 measured reflections	l = −19→18

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.2352P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.002
4620 reflections	Δρmax = 0.34 e Å−3
211 parameters	Δρmin = −0.19 e Å−3
2 restraints	Absolute structure: Flack (1983), 2025 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (3)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(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	0.362378 (12)	2.08150 (5)	0.62418 (2)	0.02405 (7)
O1	0.66851 (3)	0.45040 (16)	0.85030 (6)	0.01364 (14)
O2	0.61809 (3)	0.76090 (16)	0.59506 (6)	0.01549 (14)
N1	0.59805 (4)	0.87204 (18)	0.76135 (7)	0.01207 (15)
N2	0.56127 (4)	1.07881 (18)	0.71696 (7)	0.01267 (15)
C1	0.70999 (4)	0.2512 (2)	0.87293 (8)	0.01263 (16)
C2	0.72801 (5)	0.1294 (2)	0.97208 (8)	0.01605 (18)
H2A	0.7119	0.1758	1.0332	0.019*
C3	0.77114 (5)	−0.0650 (2)	0.97685 (9)	0.0174 (2)
H3A	0.7851	−0.1537	1.0433	0.021*
C4	0.79475 (5)	−0.1341 (2)	0.88576 (9)	0.01846 (19)
H4A	0.8245	−0.2663	0.8922	0.022*
C5	0.77532 (5)	−0.0121 (2)	0.78699 (9)	0.01828 (19)
H5A	0.7911	−0.0607	0.7256	0.022*
C6	0.73181 (4)	0.1849 (2)	0.77992 (8)	0.01348 (17)
C7	0.70075 (4)	0.3521 (2)	0.69570 (8)	0.01474 (17)
H7A	0.7049	0.3542	0.6224	0.018*
C8	0.66431 (4)	0.5062 (2)	0.74233 (8)	0.01243 (16)
C9	0.62453 (4)	0.7225 (2)	0.69371 (8)	0.01223 (17)
C10	0.53404 (4)	1.2045 (2)	0.78210 (8)	0.01311 (17)
H10A	0.5403	1.1551	0.8559	0.016*
C11	0.49318 (4)	1.4248 (2)	0.74216 (8)	0.01304 (17)
C12	0.46196 (5)	1.5490 (2)	0.81314 (9)	0.01721 (19)
H12A	0.4686	1.4950	0.8865	0.021*
C13	0.42134 (5)	1.7509 (2)	0.77787 (10)	0.0192 (2)
H13A	0.3998	1.8321	0.8261	0.023*
C14	0.41298 (4)	1.8308 (2)	0.67104 (10)	0.01754 (19)
C15	0.44432 (5)	1.7160 (2)	0.59957 (9)	0.0181 (2)
H15A	0.4386	1.7771	0.5270	0.022*
C16	0.48413 (4)	1.5106 (2)	0.63496 (8)	0.01574 (18)
H16A	0.5052	1.4284	0.5861	0.019*
O1W	0.58492 (4)	0.25083 (19)	0.47297 (6)	0.01780 (15)
H1W1	0.5989 (8)	0.402 (4)	0.5046 (15)	0.026 (5)*
H2W1	0.5934 (10)	0.127 (5)	0.510 (2)	0.044 (6)*
H1N1	0.6041 (8)	0.820 (4)	0.8315 (15)	0.021 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01451 (11)	0.01539 (10)	0.03983 (16)	0.00472 (8)	−0.00296 (10)	−0.00640 (11)
O1	0.0150 (3)	0.0136 (3)	0.0126 (3)	0.0039 (2)	0.0033 (3)	0.0011 (2)
O2	0.0206 (4)	0.0144 (3)	0.0122 (3)	0.0019 (3)	0.0046 (3)	0.0009 (3)
N1	0.0125 (4)	0.0121 (3)	0.0117 (3)	0.0020 (3)	0.0019 (3)	0.0011 (3)
N2	0.0120 (4)	0.0116 (3)	0.0144 (4)	0.0009 (3)	0.0018 (3)	0.0008 (3)
C1	0.0126 (4)	0.0109 (4)	0.0144 (4)	0.0010 (3)	0.0024 (3)	−0.0005 (3)
C2	0.0175 (5)	0.0169 (4)	0.0137 (4)	0.0026 (4)	0.0024 (4)	0.0009 (3)
C3	0.0179 (5)	0.0170 (4)	0.0164 (5)	0.0023 (3)	0.0004 (4)	0.0019 (3)
C4	0.0165 (5)	0.0183 (4)	0.0207 (5)	0.0060 (4)	0.0034 (4)	0.0012 (4)
C5	0.0186 (5)	0.0187 (4)	0.0185 (5)	0.0062 (4)	0.0060 (4)	−0.0003 (4)
C6	0.0140 (4)	0.0130 (4)	0.0140 (4)	0.0017 (3)	0.0040 (3)	0.0003 (3)
C7	0.0165 (4)	0.0147 (4)	0.0135 (4)	0.0023 (3)	0.0038 (3)	0.0009 (3)
C8	0.0134 (4)	0.0120 (4)	0.0121 (4)	0.0012 (3)	0.0026 (3)	0.0009 (3)
C9	0.0134 (4)	0.0106 (4)	0.0131 (4)	−0.0003 (3)	0.0034 (3)	0.0003 (3)
C10	0.0140 (4)	0.0127 (4)	0.0129 (4)	0.0007 (3)	0.0029 (3)	0.0007 (3)
C11	0.0124 (4)	0.0122 (4)	0.0150 (4)	0.0002 (3)	0.0039 (3)	−0.0022 (3)
C12	0.0193 (5)	0.0159 (4)	0.0180 (4)	0.0011 (4)	0.0077 (4)	−0.0020 (4)
C13	0.0169 (5)	0.0166 (4)	0.0257 (5)	0.0017 (4)	0.0080 (4)	−0.0050 (4)
C14	0.0116 (4)	0.0119 (4)	0.0284 (5)	0.0014 (3)	0.0009 (4)	−0.0040 (4)
C15	0.0175 (5)	0.0170 (4)	0.0187 (5)	0.0039 (3)	0.0000 (4)	−0.0012 (4)
C16	0.0153 (4)	0.0166 (4)	0.0155 (4)	0.0044 (3)	0.0028 (3)	−0.0007 (3)
O1W	0.0256 (4)	0.0159 (3)	0.0116 (3)	−0.0015 (3)	0.0022 (3)	0.0006 (3)

Cl1—C14	1.7407 (11)	C6—C7	1.4371 (14)
O1—C1	1.3757 (12)	C7—C8	1.3566 (14)
O1—C8	1.3785 (12)	C7—H7A	0.9500
O2—C9	1.2459 (12)	C8—C9	1.4696 (13)
N1—C9	1.3505 (12)	C10—C11	1.4690 (14)
N1—N2	1.3785 (12)	C10—H10A	0.9500
N1—H1N1	0.909 (18)	C11—C16	1.3975 (14)
N2—C10	1.2848 (13)	C11—C12	1.3984 (14)
C1—C2	1.3837 (14)	C12—C13	1.3931 (16)
C1—C6	1.4049 (13)	C12—H12A	0.9500
C2—C3	1.3896 (15)	C13—C14	1.3856 (18)
C2—H2A	0.9500	C13—H13A	0.9500
C3—C4	1.4097 (16)	C14—C15	1.3876 (16)
C3—H3A	0.9500	C15—C16	1.3916 (15)
C4—C5	1.3863 (16)	C15—H15A	0.9500
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.4025 (14)	O1W—H1W1	0.857 (19)
C5—H5A	0.9500	O1W—H2W1	0.75 (3)
C1—O1—C8	105.55 (8)	C7—C8—C9	128.60 (9)
C9—N1—N2	117.07 (8)	O1—C8—C9	118.87 (8)
C9—N1—H1N1	117.6 (12)	O2—C9—N1	124.39 (9)
N2—N1—H1N1	125.2 (12)	O2—C9—C8	119.11 (9)
C10—N2—N1	115.70 (9)	N1—C9—C8	116.48 (8)
O1—C1—C2	125.76 (9)	N2—C10—C11	119.81 (9)
O1—C1—C6	110.21 (8)	N2—C10—H10A	120.1
C2—C1—C6	124.03 (9)	C11—C10—H10A	120.1
C1—C2—C3	115.97 (10)	C16—C11—C12	119.16 (10)
C1—C2—H2A	122.0	C16—C11—C10	121.81 (9)
C3—C2—H2A	122.0	C12—C11—C10	119.02 (9)
C2—C3—C4	121.76 (10)	C13—C12—C11	120.95 (10)
C2—C3—H3A	119.1	C13—C12—H12A	119.5
C4—C3—H3A	119.1	C11—C12—H12A	119.5
C5—C4—C3	121.07 (10)	C14—C13—C12	118.71 (10)
C5—C4—H4A	119.5	C14—C13—H13A	120.6
C3—C4—H4A	119.5	C12—C13—H13A	120.6
C4—C5—C6	118.35 (10)	C13—C14—C15	121.45 (10)
C4—C5—H5A	120.8	C13—C14—Cl1	119.90 (8)
C6—C5—H5A	120.8	C15—C14—Cl1	118.65 (9)
C5—C6—C1	118.81 (9)	C14—C15—C16	119.50 (10)
C5—C6—C7	135.37 (10)	C14—C15—H15A	120.2
C1—C6—C7	105.81 (9)	C16—C15—H15A	120.2
C8—C7—C6	105.94 (9)	C15—C16—C11	120.20 (10)
C8—C7—H7A	127.0	C15—C16—H16A	119.9
C6—C7—H7A	127.0	C11—C16—H16A	119.9
C7—C8—O1	112.48 (9)	H1W1—O1W—H2W1	107 (2)
C9—N1—N2—C10	175.60 (9)	N2—N1—C9—O2	0.48 (14)
C8—O1—C1—C2	−179.09 (10)	N2—N1—C9—C8	179.00 (8)
C8—O1—C1—C6	0.46 (11)	C7—C8—C9—O2	7.15 (16)
O1—C1—C2—C3	−179.16 (10)	O1—C8—C9—O2	−175.52 (9)
C6—C1—C2—C3	1.35 (16)	C7—C8—C9—N1	−171.45 (10)
C1—C2—C3—C4	−0.30 (16)	O1—C8—C9—N1	5.88 (13)
C2—C3—C4—C5	−0.69 (18)	N1—N2—C10—C11	−179.00 (8)
C3—C4—C5—C6	0.67 (17)	N2—C10—C11—C16	−2.28 (15)
C4—C5—C6—C1	0.32 (16)	N2—C10—C11—C12	176.82 (10)
C4—C5—C6—C7	−179.70 (12)	C16—C11—C12—C13	1.54 (16)
O1—C1—C6—C5	179.05 (9)	C10—C11—C12—C13	−177.59 (10)
C2—C1—C6—C5	−1.38 (16)	C11—C12—C13—C14	−1.15 (16)
O1—C1—C6—C7	−0.94 (11)	C12—C13—C14—C15	−0.46 (17)
C2—C1—C6—C7	178.62 (10)	C12—C13—C14—Cl1	179.76 (8)
C5—C6—C7—C8	−178.95 (12)	C13—C14—C15—C16	1.64 (17)
C1—C6—C7—C8	1.04 (11)	Cl1—C14—C15—C16	−178.57 (9)
C6—C7—C8—O1	−0.81 (12)	C14—C15—C16—C11	−1.23 (16)
C6—C7—C8—C9	176.66 (10)	C12—C11—C16—C15	−0.34 (16)
C1—O1—C8—C7	0.24 (11)	C10—C11—C16—C15	178.77 (10)
C1—O1—C8—C9	−177.51 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.855 (19)	2.040 (19)	2.8815 (11)	168.1 (18)
O1W—H2W1···O2i	0.75 (2)	2.06 (2)	2.8045 (11)	173 (2)
N1—H1N1···O1Wii	0.909 (19)	1.952 (19)	2.8083 (12)	156.2 (18)
C2—H2A···O2ii	0.95	2.57	3.3710 (14)	142
C10—H10A···O1Wii	0.95	2.54	3.3067 (13)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2	0.855 (19)	2.040 (19)	2.8815 (11)	168.1 (18)
O1W—H2W1⋯O2i	0.75 (2)	2.06 (2)	2.8045 (11)	173 (2)
N1—H1N1⋯O1W ii	0.909 (19)	1.952 (19)	2.8083 (12)	156.2 (18)
C2—H2A⋯O2ii	0.95	2.57	3.3710 (14)	142
C10—H10A⋯O1W ii	0.95	2.54	3.3067 (13)	138

Symmetry codes: (i) ; (ii) .