Crystal structure of 4-{(E)-[2-(pyridin-4-ylcarbon­yl)hydrazin-1-yl­idene]meth­yl}phenyl acetate monohydrate

Datta, R.; Ramya, V.; Sithambaresan, M.; Kurup, M.R.P.

doi:10.1107/S2056989014027819

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o79-o80

doi:10.1107/S2056989014027819

Open

access

Crystal structure of 4-{(E)-[2-(pyridin-4-ylcarbonyl)hydrazin-1-ylidene]methyl}phenyl acetate monohydrate

Riya Datta,^a V. Ramya,^a M. Sithambaresan ^b ^* and M. R. Prathapachandra Kurup ^c

^aDepartment of Chemistry, Christ University, Hosur Road, Bangalore 560 029, India, ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and ^cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
^*Correspondence e-mail: msithambaresan@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 15 December 2014; accepted 20 December 2014; online 3 January 2015)

The asymmetric unit of the title compound, C₁₅H₁₃N₃O₃·H₂O, comprises a 4-{(E)-[2-(pyridin-4-ylcarbonyl)hydrazinylidene]methyl}phenyl acetate molecule and a solvent water molecule linked by O—H⋯O and O—H⋯N hydrogen bonds from the water molecule and a C—H⋯O contact from the organic molecule. 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.

Keywords: crystal structure; hydrazone; aroyl hydrazone; hydrogen bonding.

CCDC reference: 1040455

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₃N₃O₃·H₂O
M_r = 301.30
Monoclinic, P 2₁ /c
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.113
S = 0.94
2614 reflections
213 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 ).

Supporting information

CCDC reference: 1040455

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989014027819/sj5434sup1.cif

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

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

checkCIF report

Structural commentary top

Hydrazone derivatives are found to have structural diversity due to their coordinative ability (Sreeja et al., 2004; Prasanna & Kumar, 2013) arising from thioamido-thioiminol tautomerism. Ruthenium(II) complexes with such compounds as ligands have been shown to function as catalysts (Thilagavathi et al., 2010). The title compound [C₁₅H₁₃N₃O₃].(H₂O) adopts an E configuration with respect to C7═N3 bond and O1 and N3 are cis with respect to the C6—N2 bond (Fig. 1). The dihedral angle between the pyridine and benzene rings is 21.90 (7) Å. The C7═N3 [1.275 (2) Å] bond distances are very close to the formal C═N bond length, which confirms the azomethine bond formation.

There are four classical intermolecular O—H···O, O—H···N and N—H···O hydrogen bonds and three non-classical C—H···O interactions, (Table 1, Figure 2). These intermolecular hydrogen bonds build a two-dimensional network progressing along the c axis (Fig. 3). Fig. 4 shows the packing diagram of the title compound along the a axis.

Synthesis and crystallization top

The title compound was synthesised by adapting a reported procedure (Joseph et al., 2013). A solution of isonicotinic acid hydrazide (0.137 g, 1 mmol) in methanol/DMF (1:1 v/v, 10 ml) was mixed with a methanol /DMF solution (10 ml) of 4-formylphenyl acetate (0.164 g, 1 mmol). The mixture was refluxed for 6 h and then cooled to room temperature. The resulting solid was recrystallized from chloroform/methanol (1:1 v/v). Colorless, block shaped crystals suitable for XRD studies were obtained after slow evaporation of the solution in air over several days.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms bound to C were placed in calculated positions, guided by difference maps, with C—H bond distances of 0.93-0.96 Å. H atoms were assigned U_iso(H) values of 1.2Ueq(carrier). H2 on N2 and H1S & H2S of the water molecule were located in a difference Fourier map and refined with the bond distances restrained to 0.88±0.01 and 0.86±0.02 Å respectively. The low angle reflection (1 0 0) was omitted from the refinement.

Related literature top

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).

Computing details top

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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. An ORTEP view of the compound, with 50% probability displacement ellipsoids for the non-H atoms.
	Fig. 2. Graphical representation showing hydrogen bonding interactions in the crystal structure of [C₁₅H₁₃N₃O₃]·(H₂O).
	Fig. 3. The hydrogen bonding interactions build a double layer progressing along the c axis in the title compound.
	Fig. 4. A view of the overall crystal packing along the a axis.

4-{(E)-[2-(Pyridin-4-ylcarbonyl)hydrazin-1-ylidene]methyl}phenyl acetate monohydrate top

Crystal data top

C₁₅H₁₃N₃O₃·H₂O	F(000) = 632
M_r = 301.30	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0674P)² + 0.4633P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max < 0.001
S = 0.94	Δρ_max = 0.21 e Å⁻³
2614 reflections	Δρ_min = −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)

Crystal data top

C₁₅H₁₃N₃O₃·H₂O	V = 1472.8 (2) Å³
M_r = 301.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.3297 (15) Å	µ = 0.10 mm⁻¹
b = 7.3058 (7) Å	T = 296 K
c = 12.4632 (10) Å	0.50 × 0.45 × 0.40 mm
β = 111.034 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2614 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2153 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.961	R_int = 0.028
8648 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	4 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.21 e Å⁻³
2614 reflections	Δρ_min = −0.17 e Å⁻³
213 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1Sⁱ	0.93	2.56	3.375 (2)	146.8
C7—H7···O1Sⁱ	0.93	2.56	3.3655 (19)	145.1
C12—H12···O3ⁱ	0.93	2.54	3.329 (2)	142.6
N2—H2'···O1Sⁱ	0.883 (9)	2.079 (10)	2.9529 (18)	170.4 (16)
O1S—H1S···N3	0.857 (16)	2.65 (2)	3.2897 (18)	132.6 (19)
O1S—H1S···O1	0.857 (16)	2.021 (17)	2.8382 (17)	159 (2)
O1S—H2S···O3ⁱⁱ	0.860 (16)	2.379 (19)	3.1754 (19)	154 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+3/2.

Acknowledgements

The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the diffraction measurements and thank Christ University for financial support.

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Joseph, B., Sithambaresan, M. & Kurup, M. R. P. (2013). Acta Cryst. E69, o1160–o1161. CSD CrossRef CAS IUCr Journals Google Scholar
Nair, R. S., Kuriakose, M., Somasundaram, V., Shenoi, V., Kurup, M. R. P. & Srinivas, P. (2014). Life Sci. 116, 90–97. CrossRef CAS PubMed Google Scholar
Prasanna, M. K. & Kumar, K. P. (2013). Int. J. Pharm. Biomed. Sci. 4, 24–29. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575–581. Web of Science CSD CrossRef CAS Google Scholar
Thilagavathi, N., Manimaran, A., Priya, N. P., Sathya, N. & Jayabalakrishnan, C. (2010). Appl. Organomet. Chem. 24, 301–307. CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o79-o80

doi:10.1107/S2056989014027819

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 4-{(E)-[2-(pyridin-4-ylcarbon­yl)hydrazin-1-yl­­idene]meth­yl}phenyl acetate monohydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 4-{(E)-[2-(pyridin-4-ylcarbonyl)hydrazin-1-ylidene]methyl}phenyl acetate monohydrate