Crystal structure of 4-{(E)-[2-(pyridin-4-ylcarbon-yl)hydrazin-1-yl-idene]meth-yl}phenyl acetate monohydrate.

The asymmetric unit of the title compound, C15H13N3O3·H2O, comprises a 4-{(E)-[2-(pyridin-4-ylcarbon-yl)hydrazinyl-idene]meth-yl}phenyl acetate mol-ecule and a solvent water mol-ecule linked by O-H⋯O and O-H⋯N hydrogen bonds from the water mol-ecule and a C-H⋯O contact from the organic mol-ecule. The compound adopts an E conformation with respect to the azomethine bond and the dihedral angle between the pyridine and benzene rings is 21.90 (7)°. The azomethine bond [1.275 (2) Å] distance is very close to the formal C=N bond length, which confirms the azomethine bond formation. An extensive set of O-H⋯O, O-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds builds a two-dimensional network progressing along the c axis.

Related literature

For biological applications of hydrazone derivatives, see: Sreeja et al. (2004 ▸); Prasanna & Kumar (2013 ▸). For the synthesis of related compounds, see: Joseph et al. (2013 ▸); Thilagavathi et al. (2010 ▸). For the anti­cancer activity of hydrazones against cervical cancer, see: Nair et al. (2014 ▸).

Experimental

Crystal data

C15H13N3O3·H2O

M = 301.30

Monoclinic,

a = 17.3297 (15) Å

b = 7.3058 (7) Å

c = 12.4632 (10) Å

β = 111.034 (3)°

V = 1472.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.50 × 0.45 × 0.40 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.951, T max = 0.961

8648 measured reflections

2614 independent reflections

2153 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.113

S = 0.94

2614 reflections

213 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989014027819/sj5434sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027819/sj5434Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014027819/sj5434Isup3.cml

Click here for additional data file.

ORTEP . DOI: 10.1107/S2056989014027819/sj5434fig1.tif

An ORTEP view of the compound, with 50% probability displacement ellipsoids for the non-H atoms.

Click here for additional data file.

15 13 3 3 2 . DOI: 10.1107/S2056989014027819/sj5434fig2.tif

Graphical representation showing hydrogen bonding inter­actions in the crystal structure of [C15H13N3O3]·(H2O).

Click here for additional data file.

c . DOI: 10.1107/S2056989014027819/sj5434fig3.tif

The hydrogen bonding inter­actions build a double layer progressing along the c axis in the title compound.

Click here for additional data file.

a . DOI: 10.1107/S2056989014027819/sj5434fig4.tif

A view of the overall crystal packing along the a axis.

CCDC reference: 1040455

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

C15H13N3O3·H2O	F(000) = 632
Mr = 301.30	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.3297 (15) Å	Cell parameters from 4335 reflections
b = 7.3058 (7) Å	θ = 3.1–28.1°
c = 12.4632 (10) Å	µ = 0.10 mm−1
β = 111.034 (3)°	T = 296 K
V = 1472.8 (2) Å3	Block, colorless
Z = 4	0.50 × 0.45 × 0.40 mm

Bruker APEXII CCD diffractometer	2614 independent reflections
Radiation source: fine-focus sealed tube	2153 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 25.1°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −20→15
Tmin = 0.951, Tmax = 0.961	k = −8→8
8648 measured reflections	l = −11→14

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.4633P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max < 0.001
S = 0.94	Δρmax = 0.21 e Å−3
2614 reflections	Δρmin = −0.17 e Å−3
213 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
4 restraints	Extinction coefficient: 0.024 (3)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.16188 (10)	0.0685 (2)	0.93233 (14)	0.0400 (4)
H1	0.2096	0.0125	0.9817	0.048*
C2	0.08732 (10)	0.0473 (2)	0.94865 (14)	0.0427 (4)
H2	0.0868	−0.0231	1.0105	0.051*
C3	0.01996 (10)	0.2228 (3)	0.79347 (15)	0.0476 (4)
H3	−0.0287	0.2763	0.7449	0.057*
C4	0.09113 (10)	0.2527 (2)	0.77045 (14)	0.0423 (4)
H4	0.0899	0.3245	0.7082	0.051*
C5	0.16422 (9)	0.1743 (2)	0.84140 (12)	0.0340 (4)
C6	0.24113 (9)	0.2125 (2)	0.81590 (13)	0.0369 (4)
C7	0.45140 (9)	0.2232 (2)	0.97566 (13)	0.0367 (4)
H7	0.4483	0.1754	1.0431	0.044*
C8	0.53158 (9)	0.2825 (2)	0.97427 (13)	0.0340 (4)
C9	0.54021 (9)	0.3707 (2)	0.87968 (13)	0.0380 (4)
H9	0.4941	0.3887	0.8134	0.046*
C10	0.61707 (10)	0.4314 (2)	0.88411 (13)	0.0388 (4)
H10	0.6229	0.4915	0.8216	0.047*
C11	0.68496 (9)	0.4011 (2)	0.98292 (14)	0.0364 (4)
C12	0.67832 (9)	0.3173 (2)	1.07787 (13)	0.0397 (4)
H12	0.7247	0.3000	1.1440	0.048*
C13	0.60111 (10)	0.2590 (2)	1.07295 (14)	0.0395 (4)
H13	0.5957	0.2030	1.1369	0.047*
C14	0.80143 (9)	0.3873 (2)	0.92676 (13)	0.0367 (4)
C15	0.88679 (10)	0.4588 (3)	0.95589 (16)	0.0483 (4)
H15A	0.9127	0.3993	0.9089	0.072*
H15B	0.9181	0.4351	1.0354	0.072*
H15C	0.8847	0.5884	0.9421	0.072*
N1	0.01652 (8)	0.1220 (2)	0.88093 (12)	0.0455 (4)
N2	0.31362 (7)	0.18494 (18)	0.90293 (11)	0.0358 (3)
N3	0.38562 (8)	0.23535 (18)	0.88687 (11)	0.0369 (3)
O1	0.23649 (7)	0.2689 (2)	0.72122 (10)	0.0589 (4)
O1S	0.35113 (8)	0.4455 (2)	0.64055 (10)	0.0480 (3)
O2	0.76382 (7)	0.46558 (16)	0.99337 (10)	0.0446 (3)
O3	0.76890 (8)	0.27267 (19)	0.85709 (12)	0.0598 (4)
H1S	0.3278 (13)	0.387 (3)	0.6800 (18)	0.080 (7)*
H2S	0.3334 (15)	0.554 (2)	0.644 (2)	0.094 (9)*
H2'	0.3186 (11)	0.148 (2)	0.9725 (10)	0.049 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0310 (8)	0.0445 (10)	0.0443 (9)	−0.0027 (7)	0.0131 (7)	0.0066 (7)
C2	0.0399 (9)	0.0451 (10)	0.0471 (9)	−0.0080 (8)	0.0205 (7)	0.0024 (7)
C3	0.0328 (9)	0.0593 (12)	0.0497 (10)	0.0064 (8)	0.0138 (7)	0.0032 (8)
C4	0.0376 (9)	0.0498 (10)	0.0412 (8)	0.0021 (8)	0.0162 (7)	0.0055 (7)
C5	0.0308 (8)	0.0363 (9)	0.0357 (8)	−0.0045 (7)	0.0132 (6)	−0.0039 (6)
C6	0.0343 (8)	0.0403 (9)	0.0385 (8)	−0.0059 (7)	0.0158 (7)	0.0003 (7)
C7	0.0347 (9)	0.0365 (9)	0.0435 (9)	−0.0015 (7)	0.0199 (7)	0.0004 (7)
C8	0.0303 (8)	0.0330 (8)	0.0419 (8)	0.0002 (6)	0.0169 (6)	−0.0039 (6)
C9	0.0317 (8)	0.0445 (9)	0.0373 (8)	−0.0010 (7)	0.0118 (6)	−0.0013 (7)
C10	0.0391 (9)	0.0441 (9)	0.0379 (8)	−0.0048 (7)	0.0196 (7)	−0.0012 (7)
C11	0.0304 (8)	0.0386 (9)	0.0443 (8)	−0.0071 (7)	0.0184 (7)	−0.0121 (7)
C12	0.0315 (8)	0.0465 (10)	0.0395 (8)	0.0005 (7)	0.0106 (7)	−0.0013 (7)
C13	0.0388 (9)	0.0426 (9)	0.0400 (8)	−0.0003 (7)	0.0176 (7)	0.0040 (7)
C14	0.0351 (8)	0.0394 (9)	0.0378 (8)	0.0001 (7)	0.0157 (7)	−0.0018 (7)
C15	0.0375 (9)	0.0532 (11)	0.0600 (10)	−0.0045 (8)	0.0246 (8)	−0.0013 (8)
N1	0.0352 (8)	0.0526 (9)	0.0534 (8)	−0.0053 (7)	0.0216 (7)	−0.0049 (7)
N2	0.0286 (7)	0.0437 (8)	0.0394 (7)	−0.0049 (6)	0.0174 (6)	0.0019 (6)
N3	0.0305 (7)	0.0402 (8)	0.0455 (7)	−0.0042 (6)	0.0203 (6)	−0.0011 (6)
O1	0.0413 (7)	0.0937 (11)	0.0431 (7)	−0.0115 (7)	0.0168 (5)	0.0149 (7)
O1S	0.0471 (7)	0.0572 (9)	0.0459 (7)	0.0022 (6)	0.0241 (6)	0.0071 (6)
O2	0.0342 (6)	0.0543 (7)	0.0512 (7)	−0.0151 (5)	0.0223 (5)	−0.0191 (5)
O3	0.0482 (8)	0.0701 (9)	0.0660 (8)	−0.0102 (7)	0.0266 (6)	−0.0306 (7)

C1—C2	1.387 (2)	C9—H9	0.9300
C1—C5	1.384 (2)	C10—C11	1.382 (2)
C1—H1	0.9300	C10—H10	0.9300
C2—N1	1.331 (2)	C11—C12	1.374 (2)
C2—H2	0.9300	C11—O2	1.4066 (18)
C3—N1	1.334 (2)	C12—C13	1.384 (2)
C3—C4	1.380 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.382 (2)	C14—O3	1.1921 (19)
C4—H4	0.9300	C14—O2	1.3527 (18)
C5—C6	1.503 (2)	C14—C15	1.486 (2)
C6—O1	1.2252 (19)	C15—H15A	0.9600
C6—N2	1.348 (2)	C15—H15B	0.9600
C7—N3	1.275 (2)	C15—H15C	0.9600
C7—C8	1.462 (2)	N2—N3	1.3827 (17)
C7—H7	0.9300	N2—H2'	0.883 (9)
C8—C13	1.389 (2)	O1S—H1S	0.857 (16)
C8—C9	1.398 (2)	O1S—H2S	0.860 (16)
C9—C10	1.386 (2)
C2—C1—C5	119.01 (15)	C11—C10—H10	120.6
C2—C1—H1	120.5	C9—C10—H10	120.6
C5—C1—H1	120.5	C12—C11—C10	122.10 (14)
N1—C2—C1	123.81 (15)	C12—C11—O2	116.65 (14)
N1—C2—H2	118.1	C10—C11—O2	121.14 (14)
C1—C2—H2	118.1	C11—C12—C13	118.52 (14)
N1—C3—C4	124.23 (16)	C11—C12—H12	120.7
N1—C3—H3	117.9	C13—C12—H12	120.7
C4—C3—H3	117.9	C12—C13—C8	121.23 (15)
C3—C4—C5	118.91 (15)	C12—C13—H13	119.4
C3—C4—H4	120.5	C8—C13—H13	119.4
C5—C4—H4	120.5	O3—C14—O2	122.55 (14)
C4—C5—C1	117.75 (14)	O3—C14—C15	126.45 (15)
C4—C5—C6	117.81 (14)	O2—C14—C15	110.97 (14)
C1—C5—C6	124.43 (14)	C14—C15—H15A	109.5
O1—C6—N2	123.04 (14)	C14—C15—H15B	109.5
O1—C6—C5	120.63 (14)	H15A—C15—H15B	109.5
N2—C6—C5	116.31 (13)	C14—C15—H15C	109.5
N3—C7—C8	121.78 (14)	H15A—C15—H15C	109.5
N3—C7—H7	119.1	H15B—C15—H15C	109.5
C8—C7—H7	119.1	C2—N1—C3	116.29 (14)
C13—C8—C9	118.84 (14)	C6—N2—N3	118.20 (12)
C13—C8—C7	118.62 (14)	C6—N2—H2'	124.8 (11)
C9—C8—C7	122.45 (14)	N3—N2—H2'	116.7 (11)
C10—C9—C8	120.40 (14)	C7—N3—N2	115.33 (13)
C10—C9—H9	119.8	H1S—O1S—H2S	100.4 (19)
C8—C9—H9	119.8	C14—O2—C11	117.88 (12)
C11—C10—C9	118.88 (14)
C5—C1—C2—N1	0.6 (3)	C9—C10—C11—O2	−177.75 (14)
N1—C3—C4—C5	0.1 (3)	C10—C11—C12—C13	1.1 (2)
C3—C4—C5—C1	0.2 (2)	O2—C11—C12—C13	177.22 (14)
C3—C4—C5—C6	−178.71 (15)	C11—C12—C13—C8	0.6 (2)
C2—C1—C5—C4	−0.5 (2)	C9—C8—C13—C12	−1.5 (2)
C2—C1—C5—C6	178.31 (14)	C7—C8—C13—C12	−178.10 (15)
C4—C5—C6—O1	−18.5 (2)	C1—C2—N1—C3	−0.3 (2)
C1—C5—C6—O1	162.62 (17)	C4—C3—N1—C2	−0.1 (3)
C4—C5—C6—N2	160.04 (15)	O1—C6—N2—N3	4.8 (2)
C1—C5—C6—N2	−18.8 (2)	C5—C6—N2—N3	−173.74 (12)
N3—C7—C8—C13	−177.64 (15)	C8—C7—N3—N2	−176.06 (13)
N3—C7—C8—C9	5.9 (2)	C6—N2—N3—C7	173.26 (14)
C13—C8—C9—C10	0.8 (2)	O3—C14—O2—C11	3.2 (2)
C7—C8—C9—C10	177.24 (15)	C15—C14—O2—C11	−174.82 (14)
C8—C9—C10—C11	0.8 (2)	C12—C11—O2—C14	115.34 (16)
C9—C10—C11—C12	−1.8 (2)	C10—C11—O2—C14	−68.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1Si	0.93	2.56	3.375 (2)	147
C7—H7···O1Si	0.93	2.56	3.3655 (19)	145
C12—H12···O3i	0.93	2.54	3.329 (2)	143
N2—H2′···O1Si	0.88 (1)	2.08 (1)	2.9529 (18)	170 (2)
O1S—H1S···N3	0.86 (2)	2.65 (2)	3.2897 (18)	133 (2)
O1S—H1S···O1	0.86 (2)	2.02 (2)	2.8382 (17)	159 (2)
O1S—H2S···O3ii	0.86 (2)	2.38 (2)	3.1754 (19)	154 (2)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C1H1O1S i	0.93	2.56	3.375(2)	147
C7H7O1S i	0.93	2.56	3.3655(19)	145
C12H12O3i	0.93	2.54	3.329(2)	143
N2H2O1S i	0.88(1)	2.08(1)	2.9529(18)	170(2)
O1SH1SN3	0.86(2)	2.65(2)	3.2897(18)	133(2)
O1SH1SO1	0.86(2)	2.02(2)	2.8382(17)	159(2)
O1SH2SO3ii	0.86(2)	2.38(2)	3.1754(19)	154(2)

Symmetry codes: (i) ; (ii) .