4-Methyl­benzoic acid–N′-[(E)-4-methyl­benzyl­idene]pyridine-4-carbohydrazide–water (1/1/1)

Fun, H.-K.; Ooi, C.W.; Shetty, D.N.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812016868

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1492

doi:10.1107/S1600536812016868

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4-Methylbenzoic acid–N′-[(E)-4-methylbenzylidene]pyridine-4-carbohydrazide–water (1/1/1)

Hoong-Kun Fun,^a ^*‡ Chin Wei Ooi,^a Divya N. Shetty,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 April 2012; accepted 17 April 2012; online 21 April 2012)

In the title hydrated 1:1 adduct, C₈H₈O₂·C₁₄H₁₃N₃O·H₂O, the Schiff base molecule exists in an E conformation with respect to the N=C bond [1.2843 (13) Å] and the dihedral angle between the pyridine ring and the benzene ring is 1.04 (5)°. In the crystal, molecules are linked by N—H⋯O, C—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds into sheets lying parallel to the ab plane. The crystal structure also features π–π interactions with centroid–centroid distances of 3.6224 (6) and 3.7121 (6) Å.

Related literature

For related structures, see: Jing et al. (2005 ); Wang et al. (2007 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₈H₈O₂·C₁₄H₁₃N₃O·H₂O
M_r = 393.43
Orthorhombic, P b c a
a = 7.3199 (4) Å
b = 11.6311 (6) Å
c = 45.875 (2) Å
V = 3905.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.31 × 0.22 × 0.13 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.972, T_max = 0.988
59762 measured reflections
5751 independent reflections
5011 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.108
S = 1.07
5751 reflections
280 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N1	0.99 (2)	1.66 (2)	2.6347 (13)	168 (2)
O1W—H1W1⋯O1	0.887 (17)	1.927 (17)	2.7974 (11)	166.7 (16)
O1W—H2W1⋯N3ⁱ	0.89 (2)	2.14 (2)	3.0231 (12)	168.7 (17)
N2—H1N2⋯O1Wⁱⁱ	0.873 (17)	1.988 (17)	2.8120 (12)	157.0 (14)
C4—H4A⋯O1ⁱⁱⁱ	0.95	2.40	3.2796 (13)	154
C10—H10A⋯O2^iv	0.95	2.51	3.4188 (13)	160
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812016868/hb6743sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016868/hb6743Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016868/hb6743Isup3.cml

checkCIF report

Comment top

The structures of isoniazid and its various derivatives have been described previously (Wang et al., 2007; Jing et al., 2005). Here, the synthesis and crystal structure of its Schiff base derivative (I) is reported. The Schiff base, N'-[(E)-(4-methylphenyl)methylidene]pyridine-4- carbohydrazide was synthesized by the condensation of isoniazid with 4-methylbenzaldehyde in absolute alcohol in presence of hydrochloric acid. During the crystallization, the synthesized Schiff base crystallized with 4-methyl benzoic acid (which is a side product obtained by the auto-oxidation of unreacted 4-methyl benzaldehyde) and one molecule of water to form title compound (I) (Fig. 1).

The Schiff base molecule exists in an E conformation with respect to the N3 ═ C7 bond [N3 ═C7 = 1.2843 (13) Å; torsion angle N2—N3—C7—C8 = -178.00 (8)°]. The pyridine ring (N1/C1–C5) is essentially planar with a maximum deviation of 0.002 (1) Å at atoms C1 and C5. There is a slight inclination between the pyridine ring and the benzene ring (C8—C13), as indicated by the dihedral angle formed of 1.04 (5) °. The bond lengths and angles are comparable with those in related structures (Wang et al., 2007 and Jing et al., 2005).

In the crystal (Fig. 2), the molecules are linked via N2—H1N2···O1W, C4—H4A···O1, C10—H10A···O2, O1W—H1W1···O1, O1W—H2W1···N3 and O3—H1O3···N1 hydrogen bonds (Table 1) into two-dimensional networks parallel to the ab plane. The crystal structure also features π—π interactions with Cg1···Cg2 = 3.6224 (6) Å [symmetry code: 1-X, 1-Y, 1-Z] and Cg3···Cg3 = 3.7121 (6) Å [symmetry code: -1/2+X, Y, 1/2-Z], where Cg1, Cg2 and Cg3 are the centroids of N1/C1–C5, C8–C13 and C17–C22 rings, respectively.

Related literature top

For related structures, see: Jing et al. (2005); Wang et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of isoniazid (1.4 g, 0.01 mol) and 4-methylbenzaldehyde (1.2 g, 0.01 mol) in 15 ml of absolute alcohol containing two drops of hydrochloric acid was refluxed for about 3 h. On cooling, a solid was separated out. The solid was filtered out and recrystallized from DMF. Colourless blocks of (I) were grown from DMF by slow evaporation method. During the crystallization, the synthesized Schiff base was crystallized with 4-methyl benzoic acid (which was a side product obtained by the auto-oxidation of unreacted 4-methyl benzaldehyde) and one molecule of water to form the title compound (I). (M.p: 428 K).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

4-Methylbenzoic acid–N'-[(E)-4-methylbenzylidene]pyridine-4-carbohydrazide– water (1/1/1) top

Crystal data top

C₈H₈O₂·C₁₄H₁₃N₃O·H₂O	F(000) = 1664
M_r = 393.43	D_x = 1.338 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9870 reflections
a = 7.3199 (4) Å	θ = 2.7–30.1°
b = 11.6311 (6) Å	µ = 0.09 mm⁻¹
c = 45.875 (2) Å	T = 100 K
V = 3905.7 (4) Å³	Block, colourless
Z = 8	0.31 × 0.22 × 0.13 mm

Data collection top

Bruker APEX DUO CCD diffractometer	5751 independent reflections
Radiation source: fine-focus sealed tube	5011 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.972, T_max = 0.988	k = −16→15
59762 measured reflections	l = −61→64

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.051P)² + 1.7498P] where P = (F_o² + 2F_c²)/3
5751 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₈H₈O₂·C₁₄H₁₃N₃O·H₂O	V = 3905.7 (4) Å³
M_r = 393.43	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.3199 (4) Å	µ = 0.09 mm⁻¹
b = 11.6311 (6) Å	T = 100 K
c = 45.875 (2) Å	0.31 × 0.22 × 0.13 mm

Data collection top

Bruker APEX DUO CCD diffractometer	5751 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5011 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.988	R_int = 0.035
59762 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.41 e Å⁻³
5751 reflections	Δρ_min = −0.23 e Å⁻³
280 parameters

Special details top

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 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.

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 > σ(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.

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

	x	y	z	U_iso*/U_eq
O1W	0.43207 (11)	0.73964 (7)	0.507362 (18)	0.01826 (16)
O1	0.63620 (11)	0.64905 (6)	0.461214 (16)	0.01601 (15)
O2	0.69422 (12)	0.14784 (7)	0.336901 (17)	0.02270 (18)
O3	0.56737 (13)	0.31295 (8)	0.322091 (18)	0.0261 (2)
N1	0.59728 (12)	0.38603 (8)	0.376242 (19)	0.01606 (17)
N2	0.71637 (12)	0.47981 (7)	0.482605 (18)	0.01298 (16)
N3	0.75142 (12)	0.53545 (7)	0.508766 (18)	0.01307 (16)
C1	0.56364 (13)	0.54599 (9)	0.40841 (2)	0.01386 (18)
H1A	0.5261	0.6233	0.4113	0.017*
C2	0.54681 (14)	0.49497 (9)	0.38132 (2)	0.0164 (2)
H2A	0.4976	0.5388	0.3657	0.020*
C3	0.66639 (13)	0.32491 (9)	0.39840 (2)	0.01493 (19)
H3A	0.7018	0.2476	0.3949	0.018*
C4	0.68877 (13)	0.36905 (9)	0.42629 (2)	0.01328 (18)
H4A	0.7385	0.3232	0.4415	0.016*
C5	0.63617 (12)	0.48261 (8)	0.43136 (2)	0.01171 (17)
C6	0.66039 (13)	0.54445 (8)	0.45976 (2)	0.01197 (18)
C7	0.80639 (13)	0.46935 (9)	0.52941 (2)	0.01297 (18)
H7A	0.8232	0.3898	0.5256	0.016*
C8	0.84364 (13)	0.51370 (8)	0.55861 (2)	0.01218 (18)
C9	0.92034 (13)	0.43970 (9)	0.57926 (2)	0.01375 (18)
H9A	0.9517	0.3634	0.5738	0.017*
C10	0.95145 (13)	0.47632 (9)	0.60776 (2)	0.01496 (19)
H10A	1.0041	0.4249	0.6215	0.018*
C11	0.90594 (13)	0.58772 (9)	0.61626 (2)	0.01477 (19)
C12	0.82840 (13)	0.66163 (9)	0.59548 (2)	0.01501 (19)
H12A	0.7962	0.7377	0.6010	0.018*
C13	0.79782 (13)	0.62599 (9)	0.56710 (2)	0.01372 (18)
H13A	0.7458	0.6776	0.5534	0.016*
C14	0.93757 (16)	0.62885 (10)	0.64699 (2)	0.0211 (2)
H14A	1.0008	0.5689	0.6581	0.032*
H14B	0.8199	0.6458	0.6562	0.032*
H14C	1.0126	0.6986	0.6466	0.032*
C16	0.65514 (17)	0.08019 (11)	0.19543 (2)	0.0240 (2)
H16A	0.6553	−0.0038	0.1936	0.036*
H16B	0.7672	0.1113	0.1868	0.036*
H16C	0.5488	0.1117	0.1852	0.036*
C17	0.64625 (14)	0.11288 (9)	0.22720 (2)	0.0168 (2)
C18	0.69565 (14)	0.03460 (9)	0.24886 (3)	0.0182 (2)
H18A	0.7340	−0.0405	0.2435	0.022*
C19	0.68955 (14)	0.06485 (9)	0.27810 (2)	0.0166 (2)
H19A	0.7241	0.0107	0.2926	0.020*
C20	0.63260 (13)	0.17483 (9)	0.28622 (2)	0.01416 (19)
C21	0.57996 (14)	0.25295 (9)	0.26468 (2)	0.01573 (19)
H21A	0.5387	0.3275	0.2700	0.019*
C22	0.58768 (14)	0.22215 (9)	0.23551 (2)	0.0169 (2)
H22A	0.5526	0.2761	0.2210	0.020*
C23	0.63459 (14)	0.20873 (9)	0.31746 (2)	0.01617 (19)
H1N2	0.698 (2)	0.4055 (15)	0.4832 (4)	0.031 (4)*
H2W1	0.366 (3)	0.8001 (16)	0.5016 (4)	0.042 (5)*
H1W1	0.504 (2)	0.7217 (15)	0.4926 (4)	0.034 (4)*
H1O3	0.580 (3)	0.3298 (19)	0.3432 (5)	0.063 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.0218 (4)	0.0135 (4)	0.0194 (4)	0.0021 (3)	0.0042 (3)	0.0000 (3)
O1	0.0220 (4)	0.0109 (3)	0.0151 (3)	0.0003 (3)	−0.0003 (3)	0.0003 (3)
O2	0.0291 (4)	0.0237 (4)	0.0153 (4)	0.0021 (3)	−0.0009 (3)	0.0034 (3)
O3	0.0398 (5)	0.0242 (4)	0.0144 (4)	0.0109 (4)	−0.0047 (3)	−0.0053 (3)
N1	0.0162 (4)	0.0189 (4)	0.0131 (4)	−0.0010 (3)	0.0009 (3)	−0.0011 (3)
N2	0.0169 (4)	0.0108 (4)	0.0112 (4)	−0.0005 (3)	−0.0015 (3)	−0.0002 (3)
N3	0.0144 (4)	0.0138 (4)	0.0110 (4)	−0.0012 (3)	−0.0006 (3)	−0.0006 (3)
C1	0.0139 (4)	0.0137 (4)	0.0139 (4)	0.0008 (3)	0.0002 (3)	0.0016 (3)
C2	0.0175 (5)	0.0191 (5)	0.0126 (4)	0.0003 (4)	−0.0011 (3)	0.0022 (4)
C3	0.0148 (4)	0.0146 (4)	0.0154 (5)	−0.0005 (3)	0.0017 (3)	−0.0017 (4)
C4	0.0131 (4)	0.0131 (4)	0.0136 (4)	0.0003 (3)	0.0005 (3)	0.0008 (3)
C5	0.0105 (4)	0.0130 (4)	0.0116 (4)	−0.0011 (3)	0.0008 (3)	0.0004 (3)
C6	0.0110 (4)	0.0132 (4)	0.0117 (4)	−0.0010 (3)	0.0008 (3)	0.0005 (3)
C7	0.0132 (4)	0.0124 (4)	0.0133 (4)	−0.0001 (3)	0.0003 (3)	−0.0002 (3)
C8	0.0111 (4)	0.0140 (4)	0.0115 (4)	−0.0011 (3)	0.0000 (3)	0.0009 (3)
C9	0.0134 (4)	0.0134 (4)	0.0145 (4)	0.0003 (3)	0.0000 (3)	0.0011 (3)
C10	0.0138 (4)	0.0182 (5)	0.0129 (4)	0.0000 (3)	−0.0012 (3)	0.0029 (4)
C11	0.0127 (4)	0.0187 (5)	0.0128 (4)	−0.0029 (3)	0.0011 (3)	0.0001 (4)
C12	0.0153 (4)	0.0136 (4)	0.0161 (5)	−0.0016 (3)	0.0016 (3)	−0.0011 (4)
C13	0.0137 (4)	0.0133 (4)	0.0141 (4)	−0.0004 (3)	0.0002 (3)	0.0014 (3)
C14	0.0232 (5)	0.0263 (6)	0.0137 (5)	−0.0023 (4)	0.0000 (4)	−0.0028 (4)
C16	0.0248 (5)	0.0304 (6)	0.0167 (5)	−0.0025 (4)	0.0010 (4)	−0.0073 (4)
C17	0.0131 (4)	0.0206 (5)	0.0166 (5)	−0.0027 (4)	0.0001 (3)	−0.0043 (4)
C18	0.0155 (4)	0.0171 (5)	0.0221 (5)	0.0008 (4)	−0.0011 (4)	−0.0051 (4)
C19	0.0147 (4)	0.0157 (5)	0.0193 (5)	0.0002 (3)	−0.0018 (4)	0.0003 (4)
C20	0.0123 (4)	0.0163 (5)	0.0139 (4)	−0.0014 (3)	−0.0001 (3)	−0.0010 (3)
C21	0.0158 (4)	0.0150 (4)	0.0165 (5)	0.0006 (3)	−0.0003 (3)	−0.0010 (4)
C22	0.0172 (4)	0.0188 (5)	0.0147 (4)	−0.0009 (4)	−0.0015 (4)	0.0001 (4)
C23	0.0149 (4)	0.0189 (5)	0.0147 (5)	−0.0017 (4)	0.0002 (3)	0.0000 (4)

Geometric parameters (Å, º) top

O1W—H2W1	0.89 (2)	C9—H9A	0.9500
O1W—H1W1	0.884 (18)	C10—C11	1.3935 (15)
O1—C6	1.2312 (12)	C10—H10A	0.9500
O2—C23	1.2197 (13)	C11—C12	1.4035 (14)
O3—C23	1.3254 (13)	C11—C14	1.5068 (14)
O3—H1O3	0.99 (2)	C12—C13	1.3845 (14)
N1—C3	1.3396 (13)	C12—H12A	0.9500
N1—C2	1.3402 (14)	C13—H13A	0.9500
N2—C6	1.3533 (12)	C14—H14A	0.9800
N2—N3	1.3874 (11)	C14—H14B	0.9800
N2—H1N2	0.875 (17)	C14—H14C	0.9800
N3—C7	1.2843 (13)	C16—C17	1.5073 (15)
C1—C2	1.3825 (14)	C16—H16A	0.9800
C1—C5	1.3908 (13)	C16—H16B	0.9800
C1—H1A	0.9500	C16—H16C	0.9800
C2—H2A	0.9500	C17—C22	1.3944 (15)
C3—C4	1.3884 (14)	C17—C18	1.3956 (16)
C3—H3A	0.9500	C18—C19	1.3874 (15)
C4—C5	1.3954 (13)	C18—H18A	0.9500
C4—H4A	0.9500	C19—C20	1.3960 (14)
C5—C6	1.4985 (13)	C19—H19A	0.9500
C7—C8	1.4612 (13)	C20—C21	1.3966 (14)
C7—H7A	0.9500	C20—C23	1.4863 (14)
C8—C9	1.3978 (13)	C21—C22	1.3867 (14)
C8—C13	1.4035 (14)	C21—H21A	0.9500
C9—C10	1.3936 (14)	C22—H22A	0.9500

H2W1—O1W—H1W1	106.4 (16)	C13—C12—C11	121.37 (9)
C23—O3—H1O3	107.7 (13)	C13—C12—H12A	119.3
C3—N1—C2	118.28 (9)	C11—C12—H12A	119.3
C6—N2—N3	117.83 (8)	C12—C13—C8	120.06 (9)
C6—N2—H1N2	121.6 (11)	C12—C13—H13A	120.0
N3—N2—H1N2	117.7 (11)	C8—C13—H13A	120.0
C7—N3—N2	114.61 (8)	C11—C14—H14A	109.5
C2—C1—C5	119.15 (9)	C11—C14—H14B	109.5
C2—C1—H1A	120.4	H14A—C14—H14B	109.5
C5—C1—H1A	120.4	C11—C14—H14C	109.5
N1—C2—C1	122.52 (9)	H14A—C14—H14C	109.5
N1—C2—H2A	118.7	H14B—C14—H14C	109.5
C1—C2—H2A	118.7	C17—C16—H16A	109.5
N1—C3—C4	123.20 (9)	C17—C16—H16B	109.5
N1—C3—H3A	118.4	H16A—C16—H16B	109.5
C4—C3—H3A	118.4	C17—C16—H16C	109.5
C3—C4—C5	118.11 (9)	H16A—C16—H16C	109.5
C3—C4—H4A	120.9	H16B—C16—H16C	109.5
C5—C4—H4A	120.9	C22—C17—C18	118.66 (10)
C1—C5—C4	118.74 (9)	C22—C17—C16	120.50 (10)
C1—C5—C6	116.68 (9)	C18—C17—C16	120.84 (10)
C4—C5—C6	124.52 (9)	C19—C18—C17	120.98 (10)
O1—C6—N2	123.40 (9)	C19—C18—H18A	119.5
O1—C6—C5	120.29 (9)	C17—C18—H18A	119.5
N2—C6—C5	116.26 (9)	C18—C19—C20	120.00 (10)
N3—C7—C8	121.54 (9)	C18—C19—H19A	120.0
N3—C7—H7A	119.2	C20—C19—H19A	120.0
C8—C7—H7A	119.2	C19—C20—C21	119.33 (9)
C9—C8—C13	118.74 (9)	C19—C20—C23	119.83 (9)
C9—C8—C7	118.62 (9)	C21—C20—C23	120.81 (9)
C13—C8—C7	122.57 (9)	C22—C21—C20	120.23 (10)
C10—C9—C8	120.88 (9)	C22—C21—H21A	119.9
C10—C9—H9A	119.6	C20—C21—H21A	119.9
C8—C9—H9A	119.6	C21—C22—C17	120.79 (10)
C11—C10—C9	120.50 (9)	C21—C22—H22A	119.6
C11—C10—H10A	119.8	C17—C22—H22A	119.6
C9—C10—H10A	119.8	O2—C23—O3	123.14 (10)
C10—C11—C12	118.44 (9)	O2—C23—C20	123.68 (10)
C10—C11—C14	121.35 (9)	O3—C23—C20	113.18 (9)
C12—C11—C14	120.21 (10)

C6—N2—N3—C7	−179.09 (9)	C9—C10—C11—C12	0.00 (15)
C3—N1—C2—C1	0.06 (15)	C9—C10—C11—C14	179.69 (10)
C5—C1—C2—N1	0.23 (15)	C10—C11—C12—C13	−0.28 (15)
C2—N1—C3—C4	−0.23 (15)	C14—C11—C12—C13	−179.97 (9)
N1—C3—C4—C5	0.11 (15)	C11—C12—C13—C8	0.34 (15)
C2—C1—C5—C4	−0.34 (14)	C9—C8—C13—C12	−0.12 (14)
C2—C1—C5—C6	176.80 (9)	C7—C8—C13—C12	176.90 (9)
C3—C4—C5—C1	0.18 (14)	C22—C17—C18—C19	−0.95 (15)
C3—C4—C5—C6	−176.72 (9)	C16—C17—C18—C19	179.28 (10)
N3—N2—C6—O1	−1.32 (14)	C17—C18—C19—C20	0.28 (16)
N3—N2—C6—C5	175.99 (8)	C18—C19—C20—C21	0.81 (15)
C1—C5—C6—O1	−8.01 (13)	C18—C19—C20—C23	−177.12 (9)
C4—C5—C6—O1	168.95 (9)	C19—C20—C21—C22	−1.24 (15)
C1—C5—C6—N2	174.60 (9)	C23—C20—C21—C22	176.67 (9)
C4—C5—C6—N2	−8.45 (14)	C20—C21—C22—C17	0.57 (15)
N2—N3—C7—C8	−178.00 (8)	C18—C17—C22—C21	0.52 (15)
N3—C7—C8—C9	−173.70 (9)	C16—C17—C22—C21	−179.71 (10)
N3—C7—C8—C13	9.28 (15)	C19—C20—C23—O2	4.58 (16)
C13—C8—C9—C10	−0.15 (14)	C21—C20—C23—O2	−173.33 (10)
C7—C8—C9—C10	−177.30 (9)	C19—C20—C23—O3	−176.40 (9)
C8—C9—C10—C11	0.22 (15)	C21—C20—C23—O3	5.70 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N1	0.99 (2)	1.66 (2)	2.6347 (13)	168 (2)
O1W—H1W1···O1	0.887 (17)	1.927 (17)	2.7974 (11)	166.7 (16)
O1W—H2W1···N3ⁱ	0.89 (2)	2.14 (2)	3.0231 (12)	168.7 (17)
N2—H1N2···O1Wⁱⁱ	0.873 (17)	1.988 (17)	2.8120 (12)	157.0 (14)
C4—H4A···O1ⁱⁱⁱ	0.95	2.40	3.2796 (13)	154
C10—H10A···O2^iv	0.95	2.51	3.4188 (13)	160

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

Experimental details

Crystal data
Chemical formula	C₈H₈O₂·C₁₄H₁₃N₃O·H₂O
M_r	393.43
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	7.3199 (4), 11.6311 (6), 45.875 (2)
V (Å³)	3905.7 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.31 × 0.22 × 0.13

Data collection
Diffractometer	Bruker APEX DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.972, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	59762, 5751, 5011
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.108, 1.07
No. of reflections	5751
No. of parameters	280
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N1	0.99 (2)	1.66 (2)	2.6347 (13)	168 (2)
O1W—H1W1···O1	0.887 (17)	1.927 (17)	2.7974 (11)	166.7 (16)
O1W—H2W1···N3ⁱ	0.89 (2)	2.14 (2)	3.0231 (12)	168.7 (17)
N2—H1N2···O1Wⁱⁱ	0.873 (17)	1.988 (17)	2.8120 (12)	157.0 (14)
C4—H4A···O1ⁱⁱⁱ	0.95	2.40	3.2796 (13)	154
C10—H10A···O2^iv	0.95	2.51	3.4188 (13)	160

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under the Research University Grant No. 1001/PFIZIK/811160. BN thanks the UGC SAP for financial assistance for the purchase of chemicals. DNS thanks the UGC–RFSMS scheme (under SAP-Phase1) for financial assistance and Mangalore University for research facilities.

References

Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jing, Z.-L., Fan, Z., Yu, M., Chen, X. & Deng, Q.-L. (2005). Acta Cryst. E61, o3208–o3209. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, C.-L., Zhang, Z.-H. & Jing, Z.-L. (2007). Acta Cryst. E63, o4825. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

4-Methyl­benzoic acid–N′-[(E)-4-methyl­benzyl­­idene]pyridine-4-carbohydrazide–water (1/1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-Methylbenzoic acid–N′-[(E)-4-methylbenzylidene]pyridine-4-carbohydrazide–water (1/1/1)