4-Chloro-N'-[(E)-2-chloro-benzyl-idene]benzohydrazide monohydrate.

The title compound, C14H10Cl2N2O·H2O, has a nearly planar extended conformation [C-N-N-C = -173.66 (15)°]. The dihedral angle between the aromatic rings is 4.6 (2)°. The water mol-ecules alternate with benzohydrazide mol-ecules in chains formed by O-H⋯O hydrogen bonds which run parallel to the a axis. These chains are linked to neighboring chains through N-H⋯O and C-H⋯O inter-actions, forming a layer parallel to (001).

Related literature

For the biological activity of hydrazone compounds, see: Koopaei et al. (2013 ▶); Almasirad et al. (2005 ▶, 2006 ▶). For a similar structure, see: Cao (2009 ▶).

Experimental

Crystal data

C14H10Cl2N2O·H2O

M = 311.16

Monoclinic,

a = 4.6160 (5) Å

b = 12.8664 (15) Å

c = 23.681 (3) Å

β = 92.6760 (17)°

V = 1404.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 150 K

0.17 × 0.08 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.78, T max = 0.97

24861 measured reflections

3511 independent reflections

2604 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.02

3511 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814008885/rz5119sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008885/rz5119Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008885/rz5119Isup3.cml

CCDC reference: 998358

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H10Cl2N2O·H2O	F(000) = 640
Mr = 311.16	Dx = 1.471 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7842 reflections
a = 4.6160 (5) Å	θ = 2.3–28.1°
b = 12.8664 (15) Å	µ = 0.46 mm−1
c = 23.681 (3) Å	T = 150 K
β = 92.6760 (17)°	Column, colourless
V = 1404.9 (3) Å3	0.17 × 0.08 × 0.06 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3511 independent reflections
Radiation source: fine-focus sealed tube	2604 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 8.3660 pixels mm-1	θmax = 28.4°, θmin = 1.8°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −16→17
Tmin = 0.78, Tmax = 0.97	l = −31→31
24861 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)] = 0.039	Hydrogen site location: mixed
wR(F2) = 0.097	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0341P)2 + 0.6801P] where P = (Fo2 + 2Fc2)/3
3511 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	−0.46090 (11)	0.93219 (4)	0.06216 (2)	0.0343 (2)
Cl2	1.10272 (13)	1.00504 (4)	0.41832 (2)	0.0434 (2)
O1	0.4046 (3)	0.64950 (9)	0.23672 (6)	0.0271 (4)
N1	0.5525 (3)	0.80924 (11)	0.26635 (6)	0.0213 (4)
N2	0.7522 (3)	0.76724 (11)	0.30567 (6)	0.0223 (4)
C1	0.1777 (3)	0.79601 (13)	0.19187 (7)	0.0195 (5)
C2	0.0963 (4)	0.90021 (13)	0.19483 (8)	0.0229 (5)
C3	−0.1015 (4)	0.94238 (14)	0.15527 (8)	0.0246 (5)
C4	−0.2175 (4)	0.87909 (14)	0.11261 (7)	0.0228 (5)
C5	−0.1440 (4)	0.77569 (14)	0.10916 (8)	0.0267 (6)
C6	0.0548 (4)	0.73438 (14)	0.14875 (8)	0.0248 (5)
C7	0.3874 (3)	0.74541 (13)	0.23339 (7)	0.0202 (5)
C8	0.8769 (4)	0.83478 (14)	0.33826 (7)	0.0235 (5)
C9	1.0970 (4)	0.80330 (14)	0.38149 (7)	0.0231 (5)
C10	1.2181 (4)	0.87532 (15)	0.41988 (8)	0.0277 (6)
C11	1.4287 (4)	0.84754 (16)	0.46082 (8)	0.0337 (6)
C12	1.5197 (4)	0.74555 (17)	0.46427 (8)	0.0338 (6)
C13	1.4015 (4)	0.67216 (16)	0.42740 (8)	0.0315 (6)
C14	1.1943 (4)	0.70056 (15)	0.38619 (8)	0.0266 (6)
O2	0.9062 (3)	0.53028 (10)	0.23079 (6)	0.0339 (4)
H1	0.54250	0.87980	0.26400	0.0260*
H2	0.17730	0.94280	0.22430	0.0280*
H3	−0.15640	1.01340	0.15740	0.0300*
H5	−0.22840	0.73310	0.08000	0.0320*
H6	0.10770	0.66320	0.14640	0.0300*
H8	0.82620	0.90610	0.33440	0.0280*
H11	1.50920	0.89820	0.48620	0.0400*
H12	1.66410	0.72570	0.49210	0.0410*
H13	1.46280	0.60180	0.43030	0.0380*
H14	1.11690	0.64950	0.36070	0.0320*
H2A	1.04760	0.57140	0.23300	0.0410*
H2B	0.76260	0.56910	0.23510	0.0410*

	U11	U22	U33	U12	U13	U23
Cl1	0.0347 (3)	0.0399 (3)	0.0273 (3)	0.0029 (2)	−0.0098 (2)	0.0061 (2)
Cl2	0.0618 (4)	0.0240 (3)	0.0424 (3)	−0.0030 (2)	−0.0175 (3)	−0.0013 (2)
O1	0.0226 (6)	0.0179 (6)	0.0401 (8)	0.0003 (5)	−0.0062 (5)	0.0002 (5)
N1	0.0193 (7)	0.0184 (7)	0.0258 (8)	0.0001 (5)	−0.0042 (6)	0.0022 (6)
N2	0.0193 (7)	0.0230 (8)	0.0242 (8)	0.0020 (6)	−0.0027 (6)	0.0039 (6)
C1	0.0179 (8)	0.0201 (8)	0.0206 (9)	−0.0016 (6)	0.0013 (6)	0.0017 (7)
C2	0.0244 (9)	0.0201 (8)	0.0240 (9)	−0.0011 (7)	−0.0024 (7)	−0.0016 (7)
C3	0.0249 (9)	0.0217 (9)	0.0272 (10)	0.0027 (7)	0.0000 (7)	0.0015 (7)
C4	0.0202 (8)	0.0295 (9)	0.0186 (9)	−0.0006 (7)	0.0001 (7)	0.0041 (7)
C5	0.0326 (10)	0.0268 (10)	0.0203 (9)	−0.0043 (8)	−0.0035 (7)	−0.0030 (7)
C6	0.0288 (9)	0.0208 (9)	0.0247 (9)	0.0001 (7)	0.0009 (7)	−0.0020 (7)
C7	0.0166 (8)	0.0192 (8)	0.0251 (9)	−0.0010 (6)	0.0028 (6)	0.0003 (7)
C8	0.0233 (9)	0.0228 (9)	0.0243 (9)	0.0000 (7)	−0.0004 (7)	0.0018 (7)
C9	0.0202 (8)	0.0265 (9)	0.0223 (9)	−0.0036 (7)	−0.0009 (7)	0.0027 (7)
C10	0.0308 (10)	0.0265 (10)	0.0256 (10)	−0.0037 (7)	−0.0018 (8)	0.0043 (8)
C11	0.0366 (11)	0.0383 (11)	0.0252 (10)	−0.0077 (9)	−0.0082 (8)	0.0010 (9)
C12	0.0294 (10)	0.0461 (12)	0.0252 (10)	0.0031 (9)	−0.0055 (8)	0.0089 (9)
C13	0.0305 (10)	0.0340 (11)	0.0298 (11)	0.0069 (8)	−0.0003 (8)	0.0058 (8)
C14	0.0263 (9)	0.0272 (10)	0.0261 (10)	−0.0004 (7)	−0.0011 (7)	0.0014 (8)
O2	0.0232 (6)	0.0178 (6)	0.0601 (10)	−0.0009 (5)	−0.0037 (6)	0.0041 (6)

Cl1—C4	1.7410 (18)	C8—C9	1.465 (2)
Cl2—C10	1.752 (2)	C9—C10	1.397 (3)
O1—C7	1.239 (2)	C9—C14	1.399 (3)
O2—H2B	0.8400	C10—C11	1.387 (3)
O2—H2A	0.8400	C11—C12	1.379 (3)
N1—C7	1.345 (2)	C12—C13	1.381 (3)
N1—N2	1.389 (2)	C13—C14	1.383 (3)
N2—C8	1.281 (2)	C2—H2	0.9500
N1—H1	0.9100	C3—H3	0.9500
C1—C6	1.393 (2)	C5—H5	0.9500
C1—C2	1.395 (2)	C6—H6	0.9500
C1—C7	1.496 (2)	C8—H8	0.9500
C2—C3	1.388 (3)	C11—H11	0.9500
C3—C4	1.386 (3)	C12—H12	0.9500
C4—C5	1.376 (3)	C13—H13	0.9500
C5—C6	1.387 (3)	C14—H14	0.9500
H2A—O2—H2B	103.00	Cl2—C10—C11	117.56 (15)
N2—N1—C7	119.47 (14)	C10—C11—C12	119.22 (18)
N1—N2—C8	113.93 (14)	C11—C12—C13	120.19 (18)
N2—N1—H1	117.00	C12—C13—C14	120.34 (19)
C7—N1—H1	123.00	C9—C14—C13	120.97 (18)
C2—C1—C7	123.55 (15)	C3—C2—H2	120.00
C2—C1—C6	118.86 (15)	C1—C2—H2	120.00
C6—C1—C7	117.58 (15)	C2—C3—H3	121.00
C1—C2—C3	120.81 (16)	C4—C3—H3	121.00
C2—C3—C4	118.82 (16)	C6—C5—H5	120.00
Cl1—C4—C3	119.00 (14)	C4—C5—H5	120.00
C3—C4—C5	121.56 (17)	C1—C6—H6	120.00
Cl1—C4—C5	119.44 (14)	C5—C6—H6	120.00
C4—C5—C6	119.18 (17)	C9—C8—H8	120.00
C1—C6—C5	120.77 (16)	N2—C8—H8	120.00
N1—C7—C1	116.57 (14)	C10—C11—H11	120.00
O1—C7—C1	120.85 (15)	C12—C11—H11	120.00
O1—C7—N1	122.58 (15)	C13—C12—H12	120.00
N2—C8—C9	120.72 (16)	C11—C12—H12	120.00
C10—C9—C14	117.26 (16)	C12—C13—H13	120.00
C8—C9—C14	121.76 (16)	C14—C13—H13	120.00
C8—C9—C10	120.99 (16)	C9—C14—H14	120.00
Cl2—C10—C9	120.42 (14)	C13—C14—H14	120.00
C9—C10—C11	122.01 (18)
C7—N1—N2—C8	−173.66 (15)	C3—C4—C5—C6	−1.2 (3)
N2—N1—C7—O1	0.3 (2)	C4—C5—C6—C1	0.5 (3)
N2—N1—C7—C1	−179.81 (13)	N2—C8—C9—C10	−175.19 (17)
N1—N2—C8—C9	−178.99 (15)	N2—C8—C9—C14	4.7 (3)
C6—C1—C2—C3	−0.6 (3)	C8—C9—C10—Cl2	1.6 (2)
C7—C1—C2—C3	−179.41 (16)	C8—C9—C10—C11	−179.38 (17)
C2—C1—C6—C5	0.4 (3)	C14—C9—C10—Cl2	−178.37 (14)
C7—C1—C6—C5	179.20 (16)	C14—C9—C10—C11	0.7 (3)
C2—C1—C7—O1	163.87 (16)	C8—C9—C14—C13	−179.76 (17)
C2—C1—C7—N1	−16.0 (2)	C10—C9—C14—C13	0.2 (3)
C6—C1—C7—O1	−14.9 (2)	Cl2—C10—C11—C12	178.38 (15)
C6—C1—C7—N1	165.23 (15)	C9—C10—C11—C12	−0.7 (3)
C1—C2—C3—C4	0.0 (3)	C10—C11—C12—C13	−0.1 (3)
C2—C3—C4—Cl1	−178.89 (14)	C11—C12—C13—C14	1.0 (3)
C2—C3—C4—C5	0.9 (3)	C12—C13—C14—C9	−1.0 (3)
Cl1—C4—C5—C6	178.61 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.91	1.95	2.8510 (19)	168
O2—H2A···O1ii	0.84	1.93	2.7632 (19)	172
O2—H2B···O1	0.84	1.95	2.7864 (19)	172
C2—H2···O2i	0.95	2.43	3.286 (2)	150
C8—H8···O2i	0.95	2.44	3.242 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.91	1.95	2.8510 (19)	168
O2—H2A⋯O1ii	0.84	1.93	2.7632 (19)	172
O2—H2B⋯O1	0.84	1.95	2.7864 (19)	172
C2—H2⋯O2i	0.95	2.43	3.286 (2)	150
C8—H8⋯O2i	0.95	2.44	3.242 (2)	143

Symmetry codes: (i) ; (ii) .