(2E)-N'-[(E)-4-Chloro-benzyl-idene]-3-phenyl-prop-2-enohydrazide monohydrate.

The conformation about each of the imine and ethene bonds in the title hydrazide hydrate, C(16)H(13)ClN(2)O·H(2)O, is E. The hydrazide mol-ecule is approximately planar (r.m.s. deviation of the 20 non-H atoms = 0.172 Å). The most significant twist occurs about the ethene bond [C-C=C-C = 164.1 (5)°] and the dihedral angle formed between the benzene rings is 5.3 (2)°]. In the crystal, the presence of N-H⋯O(w) and O-H⋯O(c) (× 2; w = water and c = carbon-yl) hydrogen bonds leads to a supra-molecular array in the bc plane.

Related literature

For background to the resurgence of tuberculosis; see Bezerra et al. (2006 ▶); Chung & Shin (2007 ▶); Naz et al. (2006 ▶). For background to the biological activity of n class="Chemical">trans-cinnamic acid derivatives, see: Carvalho et al. (2008 ▶). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C16H13ClN2O·n class="Chemical">H2O

M = 302.75

Monoclinic,

a = 34.078 (3) Å

b = 5.9824 (6) Å

c = 7.2912 (6) Å

β = 95.674 (3)°

V = 1479.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 120 K

0.10 × 0.08 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.492, T max = 1.000

8532 measured reflections

2572 independent reflections

2016 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.196

S = 1.05

2572 reflections

199 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.37 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003388X/hb5594sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003388X/hb5594Isup2.hkl

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

C16H13ClN2O·H2O	F(000) = 632
Mr = 302.75	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19841 reflections
a = 34.078 (3) Å	θ = 2.9–27.5°
b = 5.9824 (6) Å	µ = 0.26 mm−1
c = 7.2912 (6) Å	T = 120 K
β = 95.674 (3)°	Block, colourless
V = 1479.2 (2) Å3	0.10 × 0.08 × 0.03 mm
Z = 4

Nonius KappaCCD diffractometer	2572 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2016 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.066
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −40→39
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −7→7
Tmin = 0.492, Tmax = 1.000	l = −8→8
8532 measured reflections

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0421P)2 + 8.0472P] where P = (Fo2 + 2Fc2)/3
2572 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.36 e Å−3
4 restraints	Δρmin = −0.37 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl	0.02800 (3)	−0.2977 (2)	0.18849 (16)	0.0315 (4)
O1	0.28173 (10)	−0.0171 (6)	0.2229 (5)	0.0330 (9)
N1	0.20834 (11)	0.1523 (7)	0.1857 (5)	0.0280 (10)
N2	0.24086 (12)	0.2830 (8)	0.1657 (6)	0.0299 (10)
H2N	0.2398 (16)	0.420 (3)	0.129 (7)	0.036*
C1	0.07011 (13)	−0.1339 (9)	0.1827 (6)	0.0240 (11)
C2	0.10625 (13)	−0.2220 (9)	0.2528 (6)	0.0238 (10)
H2	0.1074	−0.3662	0.3077	0.029*
C3	0.14047 (13)	−0.1007 (8)	0.2430 (6)	0.0235 (11)
H3	0.1652	−0.1615	0.2906	0.028*
C4	0.13869 (13)	0.1134 (8)	0.1623 (6)	0.0221 (10)
C5	0.10192 (13)	0.2008 (9)	0.0959 (6)	0.0239 (10)
H5	0.1004	0.3458	0.0425	0.029*
C6	0.06758 (13)	0.0787 (9)	0.1071 (6)	0.0267 (11)
H6	0.0427	0.1401	0.0635	0.032*
C7	0.17447 (14)	0.2426 (9)	0.1444 (6)	0.0260 (11)
H7	0.1727	0.3929	0.1023	0.031*
C8	0.27682 (14)	0.1859 (9)	0.1837 (6)	0.0282 (11)
C9	0.30969 (14)	0.3385 (9)	0.1550 (6)	0.0290 (11)
H9	0.3046	0.4928	0.1329	0.035*
C10	0.34638 (14)	0.2621 (10)	0.1598 (6)	0.0296 (12)
H10	0.3503	0.1079	0.1869	0.036*
C11	0.38178 (14)	0.3936 (9)	0.1270 (6)	0.0295 (12)
C12	0.41917 (14)	0.3067 (10)	0.1809 (7)	0.0339 (12)
H12	0.4215	0.1632	0.2367	0.041*
C13	0.45299 (15)	0.4277 (11)	0.1540 (7)	0.0388 (14)
H13	0.4783	0.3688	0.1935	0.047*
C14	0.44946 (15)	0.6344 (11)	0.0691 (7)	0.0372 (14)
H14	0.4725	0.7163	0.0482	0.045*
C15	0.41234 (15)	0.7235 (10)	0.0140 (7)	0.0342 (13)
H15	0.4102	0.8662	−0.0433	0.041*
C16	0.37871 (14)	0.6055 (9)	0.0424 (6)	0.0305 (12)
H16	0.3535	0.6670	0.0049	0.037*
O1W	0.23087 (11)	0.6983 (6)	−0.0131 (5)	0.0349 (9)
H1W	0.2424 (14)	0.797 (8)	0.055 (6)	0.052*
H2W	0.2444 (13)	0.668 (9)	−0.101 (5)	0.052*

	U11	U22	U33	U12	U13	U23
Cl	0.0216 (6)	0.0401 (8)	0.0329 (6)	−0.0052 (6)	0.0028 (5)	0.0042 (6)
O1	0.0311 (19)	0.031 (2)	0.037 (2)	−0.0030 (17)	0.0035 (15)	0.0053 (17)
N1	0.025 (2)	0.036 (3)	0.023 (2)	−0.0076 (19)	0.0022 (16)	0.0007 (19)
N2	0.025 (2)	0.033 (3)	0.032 (2)	−0.006 (2)	0.0062 (17)	0.002 (2)
C1	0.019 (2)	0.033 (3)	0.021 (2)	−0.004 (2)	0.0050 (18)	0.001 (2)
C2	0.025 (2)	0.030 (3)	0.016 (2)	−0.002 (2)	0.0004 (18)	−0.001 (2)
C3	0.022 (2)	0.024 (3)	0.024 (2)	0.002 (2)	0.0024 (19)	−0.004 (2)
C4	0.022 (2)	0.026 (3)	0.019 (2)	0.000 (2)	0.0047 (18)	0.001 (2)
C5	0.028 (2)	0.024 (3)	0.020 (2)	0.003 (2)	0.0014 (18)	−0.004 (2)
C6	0.021 (2)	0.032 (3)	0.028 (3)	0.005 (2)	0.0063 (19)	−0.001 (2)
C7	0.027 (3)	0.025 (3)	0.027 (2)	−0.001 (2)	0.006 (2)	0.001 (2)
C8	0.028 (3)	0.034 (3)	0.022 (2)	−0.005 (2)	0.0005 (19)	−0.004 (2)
C9	0.027 (3)	0.030 (3)	0.029 (2)	−0.008 (2)	0.003 (2)	0.002 (2)
C10	0.029 (3)	0.040 (3)	0.019 (2)	0.000 (2)	−0.0007 (19)	0.001 (2)
C11	0.022 (2)	0.041 (3)	0.025 (2)	0.001 (2)	0.0002 (19)	−0.001 (2)
C12	0.030 (3)	0.043 (3)	0.029 (3)	−0.004 (3)	0.004 (2)	0.000 (3)
C13	0.027 (3)	0.062 (4)	0.027 (3)	0.003 (3)	0.001 (2)	−0.006 (3)
C14	0.027 (3)	0.059 (4)	0.027 (3)	−0.012 (3)	0.006 (2)	−0.002 (3)
C15	0.038 (3)	0.039 (3)	0.027 (3)	−0.008 (3)	0.008 (2)	−0.004 (2)
C16	0.025 (3)	0.043 (3)	0.022 (2)	−0.005 (2)	−0.0036 (19)	0.000 (2)
O1W	0.040 (2)	0.031 (2)	0.034 (2)	−0.0018 (18)	0.0060 (16)	−0.0059 (17)

Cl—C1	1.742 (5)	C8—C9	1.476 (7)
O1—C8	1.256 (6)	C9—C10	1.328 (7)
N1—C7	1.283 (6)	C9—H9	0.9500
N1—N2	1.376 (6)	C10—C11	1.479 (7)
N2—C8	1.351 (6)	C10—H10	0.9500
N2—H2N	0.86 (2)	C11—C12	1.396 (7)
C1—C6	1.385 (7)	C11—C16	1.409 (8)
C1—C2	1.390 (6)	C12—C13	1.392 (7)
C2—C3	1.381 (6)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.382 (8)
C3—C4	1.408 (7)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.395 (7)
C4—C5	1.399 (6)	C14—H14	0.9500
C4—C7	1.461 (6)	C15—C16	1.379 (7)
C5—C6	1.389 (7)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	O1W—H1W	0.84 (5)
C7—H7	0.9500	O1W—H2W	0.85 (4)
C7—N1—N2	116.8 (4)	N2—C8—C9	114.5 (5)
C8—N2—N1	118.5 (4)	C10—C9—C8	120.6 (5)
C8—N2—H2N	117 (4)	C10—C9—H9	119.7
N1—N2—H2N	124 (4)	C8—C9—H9	119.7
C6—C1—C2	120.8 (4)	C9—C10—C11	126.4 (5)
C6—C1—Cl	120.5 (4)	C9—C10—H10	116.8
C2—C1—Cl	118.7 (4)	C11—C10—H10	116.8
C3—C2—C1	120.2 (5)	C12—C11—C16	119.0 (5)
C3—C2—H2	119.9	C12—C11—C10	119.5 (5)
C1—C2—H2	119.9	C16—C11—C10	121.5 (4)
C2—C3—C4	119.8 (4)	C13—C12—C11	120.8 (6)
C2—C3—H3	120.1	C13—C12—H12	119.6
C4—C3—H3	120.1	C11—C12—H12	119.6
C5—C4—C3	119.0 (4)	C14—C13—C12	119.5 (5)
C5—C4—C7	119.9 (4)	C14—C13—H13	120.3
C3—C4—C7	121.1 (4)	C12—C13—H13	120.3
C6—C5—C4	120.9 (5)	C13—C14—C15	120.5 (5)
C6—C5—H5	119.5	C13—C14—H14	119.8
C4—C5—H5	119.5	C15—C14—H14	119.8
C1—C6—C5	119.1 (4)	C16—C15—C14	120.3 (5)
C1—C6—H6	120.4	C16—C15—H15	119.9
C5—C6—H6	120.4	C14—C15—H15	119.9
N1—C7—C4	119.7 (5)	C15—C16—C11	120.0 (5)
N1—C7—H7	120.1	C15—C16—H16	120.0
C4—C7—H7	120.1	C11—C16—H16	120.0
O1—C8—N2	122.5 (5)	H1W—O1W—H2W	110 (3)
O1—C8—C9	123.0 (5)
C7—N1—N2—C8	−171.2 (4)	N1—N2—C8—C9	178.4 (4)
C6—C1—C2—C3	−1.9 (7)	O1—C8—C9—C10	3.8 (7)
Cl—C1—C2—C3	177.1 (3)	N2—C8—C9—C10	−176.7 (4)
C1—C2—C3—C4	0.2 (7)	C8—C9—C10—C11	177.7 (4)
C2—C3—C4—C5	1.0 (6)	C9—C10—C11—C12	164.1 (5)
C2—C3—C4—C7	−177.9 (4)	C9—C10—C11—C16	−15.9 (8)
C3—C4—C5—C6	−0.7 (6)	C16—C11—C12—C13	0.8 (7)
C7—C4—C5—C6	178.3 (4)	C10—C11—C12—C13	−179.2 (4)
C2—C1—C6—C5	2.3 (7)	C11—C12—C13—C14	−1.4 (8)
Cl—C1—C6—C5	−176.7 (3)	C12—C13—C14—C15	1.3 (8)
C4—C5—C6—C1	−1.0 (7)	C13—C14—C15—C16	−0.5 (8)
N2—N1—C7—C4	180.0 (4)	C14—C15—C16—C11	−0.1 (7)
C5—C4—C7—N1	−172.0 (4)	C12—C11—C16—C15	0.0 (7)
C3—C4—C7—N1	7.0 (7)	C10—C11—C16—C15	180.0 (4)
N1—N2—C8—O1	−2.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1w	0.86 (2)	1.97 (3)	2.811 (6)	165 (5)
O1w—H1w···O1i	0.84 (5)	2.05 (5)	2.877 (5)	166 (4)
O1w—H2w···O1ii	0.85 (4)	2.10 (4)	2.923 (5)	165 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O1w	0.86 (2)	1.97 (3)	2.811 (6)	165 (5)
O1w—H1w⋯O1i	0.84 (5)	2.05 (5)	2.877 (5)	166 (4)
O1w—H2w⋯O1ii	0.85 (4)	2.10 (4)	2.923 (5)	165 (5)

Symmetry codes: (i) ; (ii) .