N′-[(E)-4-Benz­yloxy-2-hy­droxy­benzyl­idene]-4-nitro­benzohydrazide monohydrate

Joseph, B.; Sithambaresan, M.; Kurup, M.R.P.

doi:10.1107/S1600536812015401

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1421-o1422

doi:10.1107/S1600536812015401

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N′-[(E)-4-Benzyloxy-2-hydroxybenzylidene]-4-nitrobenzohydrazide monohydrate

Bibitha Joseph,^a M. Sithambaresan ^b ^* and M. R. Prathapachandra Kurup ^a

^aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
^*Correspondence e-mail: eesans@yahoo.com

(Received 19 March 2012; accepted 9 April 2012; online 18 April 2012)

The title compound, C₂₁H₁₇N₃O₅·H₂O, exists in the keto form with an E conformation with respect to the azomethine double bond. The twist angles between the aromatic rings are in the range 4.67 (10)–17.54 (10)°. A water molecule of solvation is present in the lattice. A conventional intramolecular O—H⋯N hydrogen bond increases the rigidity of the molecule. Intermolecular O—H⋯O, N—H⋯O and C—H⋯O hydrogen-bonding interactions establish a supramolecular linkage among the molecules in the crystal structure. There are also C—H⋯π interactions present.

Related literature

For the biological and other applications of carbohydrazides, see: Lakshmi et al. (2011 ); Grande et al. (2007 ); Naseema et al. (2010 ). For the synthesis, see: Emmanuel et al. (2011 ). For related structures of carbohydrazides, see: Fun et al. (2008 ). For the keto form, see: Bakir & Brown (2002 ).

Experimental

Crystal data

C₂₁H₁₇N₃O₅·H₂O
M_r = 409.39
Monoclinic, P c
a = 4.6275 (7) Å
b = 6.5332 (11) Å
c = 31.856 (5) Å
β = 92.417 (4)°
V = 962.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.30 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.969, T_max = 0.974
7388 measured reflections
1713 independent reflections
1663 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.088
S = 1.05
1713 reflections
288 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O1Sⁱ	0.86 (2)	2.57 (4)	3.058 (3)	117 (4)
O4—H4O⋯N3	0.86 (2)	1.93 (3)	2.670 (2)	143 (4)
N2—H2N⋯O1S	0.86 (2)	2.01 (2)	2.855 (3)	166 (3)
O1S—H2S⋯O4ⁱⁱ	0.87 (2)	2.01 (2)	2.860 (3)	165 (4)
O1S—H1S⋯O3ⁱⁱⁱ	0.88 (2)	1.80 (2)	2.676 (3)	175 (5)
C14—H14⋯O1S	0.93	2.37	3.184 (2)	146
C21—H21⋯O1S	0.93	2.43	3.325 (3)	161
C7—H7B⋯Cg^iv	0.97	2.69	3.472 (2)	138
Symmetry codes: (i) x, y+1, z; (ii) x-1, y-1, z; (iii) x, y-1, z; (iv) x-1, y, z.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812015401/fj2537sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015401/fj2537Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015401/fj2537Isup3.cml

checkCIF report

Comment top

There is growing interest in the structural features of carbohydrazides as they show a wide range of biological activities, with potential uses in antibacterial, antifungal and anticancer studies (Lakshmi et al., 2011; Grande et al., 2007). Hydrazones and their metal complexes have found applications in chemical processes like non linear optics, sensors etc. (Naseema et al., 2010).

The title compound N'-{(E)-[4-(benzyloxy)-2-hydroxyphenyl]methylidene}-4-nitrobenzohydrazide hydrate is found to exist in the E configuration with respect to N3=C14 bond. A perspective view of the molecular structure of the title compound, along with the atom-labeling is shown in Fig. 1. The bond length of C15=O3 [1.229 (2) Å] shows a significant double-bond character (Fun et al.., 2008) indicating that the molecule exists in the keto form in the solid state (Bakir & Brown, 2002) and the dihedral angles between the aromatic rings are in the range of 4.67 (10) -17.54 (10)°.

The lattice water molecule plays an essential role in packing of the molecules forming conventional and non-conventional hydrogen bonds between the carbohydrazide and water molecules (Fig. 2). A C–H···π interaction is also observed in the crystal structure between one of the H atoms attached to the C7 carbon atom and the phenyl ring of the adjacent molecule in the crystal system (Fig. 3). Two types of very weak π–π interactions also present with a shortest centroid-centroid distance of 4.9302 (14) Å. In crystal packing, the parallel arrangement of the molecules along a axis is shown in Fig. 4.

Related literature top

For the biological and other applications of carbohydrazides, see: Lakshmi et al. (2011); Grande et al. (2007); Naseema et al. (2010). For the synthesis, see: Emmanuel et al. (2011). For related structures of carbohydrazides, see: Fun et al. (2008). For the keto form, see: Bakir & Brown (2002).

Experimental top

The title compound was prepared by adapting a reported procedure (Emmanuel et al., 2011) by refluxing a mixture of methanolic solutions of 4-nitrobenzohydrazide (0.181 g, 1 mmol) and 4-(benzyloxy)-2-hydroxybenzaldehyde (0.228 g, 1 mmol) for 4 h. The formed crystals were collected, washed with few drops of methanol and dried over P₄O₁₀ in vacuo. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation from its methanolic solution.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP view of the molecular structure of the title compound, along with the atom-labelling, drawn with 50% probability displacement ellipsoids.
	Fig. 2. A view of the conventional and non-conventional hydrogen bonding interactions
	Fig. 3. Graphical representation showing C–H···π interaction in the crystal structure of C₂₁H₁₇N₃O₅.H₂O.
	Fig. 4. Packing arrangement of molecules along a axis.

N'-[(E)-4-Benzyloxy-2-hydroxybenzylidene]-4-nitrobenzohydrazide monohydrate top

Crystal data top

C₂₁H₁₇N₃O₅·H₂O	F(000) = 428.0
M_r = 409.39	D_x = 1.413 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 4698 reflections
a = 4.6275 (7) Å	θ = 3.1–28.2°
b = 6.5332 (11) Å	µ = 0.11 mm⁻¹
c = 31.856 (5) Å	T = 296 K
β = 92.417 (4)°	Block, yellow
V = 962.2 (3) Å³	0.30 × 0.28 × 0.25 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	1713 independent reflections
Radiation source: fine-focus sealed tube	1663 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω and ϕ scan	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −3→5
T_min = 0.969, T_max = 0.974	k = −7→7
7388 measured reflections	l = −37→37

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0687P)² + 0.0484P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.011
1713 reflections	Δρ_max = 0.14 e Å⁻³
288 parameters	Δρ_min = −0.16 e Å⁻³
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (7)

Crystal data top

C₂₁H₁₇N₃O₅·H₂O	V = 962.2 (3) Å³
M_r = 409.39	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 4.6275 (7) Å	µ = 0.11 mm⁻¹
b = 6.5332 (11) Å	T = 296 K
c = 31.856 (5) Å	0.30 × 0.28 × 0.25 mm
β = 92.417 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1713 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1663 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.974	R_int = 0.020
7388 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	7 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.14 e Å⁻³
1713 reflections	Δρ_min = −0.16 e Å⁻³
288 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.

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
O1	−0.5580 (7)	0.1667 (5)	0.47190 (9)	0.0986 (10)
O2	−0.5671 (7)	0.4470 (5)	0.50699 (9)	0.0960 (9)
O3	0.3371 (5)	0.9071 (3)	0.37071 (7)	0.0673 (6)
O4	0.8452 (4)	1.0067 (3)	0.26751 (6)	0.0537 (5)
O5	1.4446 (4)	0.8132 (2)	0.15654 (5)	0.0428 (4)
O1S	0.3303 (5)	0.1942 (3)	0.31076 (7)	0.0596 (5)
N1	−0.4868 (6)	0.3450 (5)	0.47795 (8)	0.0623 (7)
N2	0.3751 (4)	0.6173 (3)	0.33257 (6)	0.0380 (4)
N3	0.5600 (4)	0.7064 (3)	0.30472 (6)	0.0370 (4)
C1	1.8112 (6)	0.8824 (4)	0.09200 (9)	0.0507 (6)
H1	1.7528	0.7502	0.0983	0.061*
C2	2.0020 (6)	0.9151 (5)	0.05996 (9)	0.0593 (8)
H2	2.0703	0.8044	0.0449	0.071*
C3	2.0894 (6)	1.1089 (5)	0.05048 (9)	0.0589 (8)
H3	2.2186	1.1292	0.0293	0.071*
C4	1.9873 (6)	1.2742 (5)	0.07214 (9)	0.0600 (7)
H4	2.0454	1.4061	0.0654	0.072*
C5	1.7976 (6)	1.2430 (4)	0.10394 (9)	0.0508 (6)
H5	1.7282	1.3546	0.1186	0.061*
C6	1.7094 (4)	1.0458 (4)	0.11423 (7)	0.0377 (5)
C7	1.5050 (5)	1.0238 (4)	0.14926 (7)	0.0391 (5)
H7A	1.5901	1.0846	0.1747	0.047*
H7B	1.3264	1.0957	0.1421	0.047*
C8	1.2534 (4)	0.7701 (4)	0.18637 (7)	0.0355 (5)
C9	1.1417 (5)	0.9148 (3)	0.21297 (7)	0.0371 (5)
H9	1.1963	1.0513	0.2108	0.044*
C10	0.9484 (4)	0.8566 (4)	0.24291 (7)	0.0345 (5)
C11	0.8636 (4)	0.6529 (4)	0.24699 (7)	0.0346 (5)
C12	0.9782 (5)	0.5107 (4)	0.21932 (8)	0.0430 (5)
H12	0.9233	0.3742	0.2212	0.052*
C13	1.1688 (5)	0.5665 (4)	0.18961 (8)	0.0434 (5)
H13	1.2415	0.4686	0.1717	0.052*
C14	0.6665 (5)	0.5843 (4)	0.27812 (7)	0.0388 (5)
H14	0.6156	0.4467	0.2788	0.047*
C15	0.2747 (5)	0.7263 (4)	0.36431 (8)	0.0405 (5)
C16	0.0762 (5)	0.6172 (4)	0.39327 (7)	0.0382 (5)
C17	−0.0090 (6)	0.7250 (4)	0.42798 (8)	0.0522 (6)
H17	0.0583	0.8576	0.4326	0.063*
C18	−0.1943 (6)	0.6370 (5)	0.45600 (8)	0.0567 (7)
H18	−0.2526	0.7092	0.4793	0.068*
C19	−0.2898 (5)	0.4403 (4)	0.44837 (7)	0.0452 (6)
C20	−0.2096 (6)	0.3294 (4)	0.41418 (9)	0.0524 (6)
H20	−0.2769	0.1967	0.4098	0.063*
C21	−0.0266 (6)	0.4198 (4)	0.38649 (8)	0.0494 (6)
H21	0.0285	0.3474	0.3630	0.059*
H1S	0.325 (10)	0.105 (6)	0.3313 (11)	0.096 (14)*
H2S	0.169 (6)	0.160 (6)	0.2975 (12)	0.099 (14)*
H2N	0.336 (6)	0.489 (3)	0.3287 (9)	0.046 (7)*
H4O	0.730 (7)	0.958 (7)	0.2853 (11)	0.090 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.123 (2)	0.097 (2)	0.0791 (17)	−0.0492 (18)	0.0467 (15)	−0.0001 (15)
O2	0.1081 (19)	0.108 (2)	0.0771 (16)	−0.0053 (17)	0.0631 (14)	−0.0006 (15)
O3	0.1030 (17)	0.0439 (11)	0.0571 (11)	−0.0205 (10)	0.0283 (10)	−0.0053 (9)
O4	0.0609 (11)	0.0409 (10)	0.0623 (11)	−0.0109 (8)	0.0384 (9)	−0.0097 (8)
O5	0.0446 (8)	0.0385 (9)	0.0470 (9)	0.0009 (8)	0.0217 (7)	0.0040 (7)
O1S	0.0790 (14)	0.0383 (9)	0.0638 (12)	−0.0155 (9)	0.0283 (10)	−0.0050 (9)
N1	0.0571 (14)	0.0820 (19)	0.0491 (12)	−0.0043 (13)	0.0172 (11)	0.0143 (13)
N2	0.0434 (10)	0.0318 (10)	0.0400 (10)	−0.0066 (8)	0.0150 (8)	0.0050 (8)
N3	0.0357 (10)	0.0364 (10)	0.0398 (10)	−0.0075 (8)	0.0127 (7)	0.0060 (8)
C1	0.0523 (14)	0.0453 (14)	0.0560 (15)	−0.0009 (12)	0.0202 (12)	0.0008 (11)
C2	0.0609 (17)	0.065 (2)	0.0547 (15)	0.0085 (14)	0.0296 (13)	−0.0029 (13)
C3	0.0500 (14)	0.081 (2)	0.0477 (14)	0.0040 (14)	0.0227 (11)	0.0143 (15)
C4	0.0598 (16)	0.0594 (17)	0.0624 (17)	−0.0058 (14)	0.0212 (13)	0.0237 (15)
C5	0.0517 (14)	0.0444 (14)	0.0579 (14)	0.0025 (11)	0.0195 (11)	0.0093 (12)
C6	0.0303 (10)	0.0455 (12)	0.0378 (11)	0.0008 (10)	0.0089 (9)	0.0078 (10)
C7	0.0378 (11)	0.0382 (12)	0.0420 (12)	0.0016 (10)	0.0118 (9)	0.0024 (10)
C8	0.0334 (11)	0.0391 (12)	0.0346 (10)	0.0020 (9)	0.0097 (8)	0.0037 (9)
C9	0.0390 (11)	0.0304 (11)	0.0426 (12)	−0.0034 (9)	0.0106 (9)	0.0016 (9)
C10	0.0353 (11)	0.0327 (12)	0.0362 (11)	−0.0026 (9)	0.0100 (8)	−0.0011 (9)
C11	0.0312 (10)	0.0356 (12)	0.0374 (11)	−0.0039 (9)	0.0066 (9)	0.0019 (9)
C12	0.0457 (12)	0.0300 (11)	0.0542 (14)	−0.0021 (10)	0.0139 (10)	0.0002 (10)
C13	0.0454 (12)	0.0365 (12)	0.0497 (12)	0.0018 (10)	0.0174 (10)	−0.0052 (10)
C14	0.0382 (11)	0.0338 (12)	0.0452 (12)	−0.0049 (9)	0.0102 (10)	0.0073 (9)
C15	0.0459 (12)	0.0373 (12)	0.0389 (11)	−0.0050 (10)	0.0095 (9)	0.0028 (10)
C16	0.0393 (11)	0.0419 (12)	0.0341 (11)	0.0032 (10)	0.0082 (9)	0.0054 (9)
C17	0.0611 (16)	0.0511 (15)	0.0455 (13)	−0.0088 (13)	0.0140 (11)	−0.0051 (12)
C18	0.0648 (16)	0.0659 (17)	0.0409 (13)	−0.0006 (14)	0.0201 (11)	−0.0074 (13)
C19	0.0388 (12)	0.0614 (17)	0.0362 (12)	0.0002 (11)	0.0100 (9)	0.0102 (11)
C20	0.0569 (15)	0.0443 (14)	0.0575 (15)	−0.0059 (12)	0.0198 (12)	0.0053 (12)
C21	0.0580 (15)	0.0452 (14)	0.0468 (13)	−0.0061 (12)	0.0232 (11)	−0.0028 (11)

Geometric parameters (Å, º) top

O1—N1	1.224 (4)	C6—C7	1.500 (3)
O2—N1	1.211 (4)	C7—H7A	0.9700
O3—C15	1.231 (3)	C7—H7B	0.9700
O4—C10	1.355 (3)	C8—C9	1.384 (3)
O4—H4O	0.86 (2)	C8—C13	1.392 (4)
O5—C8	1.355 (3)	C9—C10	1.388 (3)
O5—C7	1.425 (3)	C9—H9	0.9300
O1S—H1S	0.88 (2)	C10—C11	1.395 (3)
O1S—H2S	0.873 (19)	C11—C12	1.400 (3)
N1—C19	1.476 (3)	C11—C14	1.446 (3)
N2—C15	1.336 (3)	C12—C13	1.370 (3)
N2—N3	1.386 (3)	C12—H12	0.9300
N2—H2N	0.863 (19)	C13—H13	0.9300
N3—C14	1.277 (3)	C14—H14	0.9300
C1—C6	1.375 (4)	C15—C16	1.508 (3)
C1—C2	1.394 (4)	C16—C17	1.383 (4)
C1—H1	0.9300	C16—C21	1.388 (4)
C2—C3	1.367 (5)	C17—C18	1.388 (4)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.376 (5)	C18—C19	1.377 (4)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.383 (4)	C19—C20	1.372 (4)
C4—H4	0.9300	C20—C21	1.381 (4)
C5—C6	1.394 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—H21	0.9300

C10—O4—H4O	111 (3)	C8—C9—H9	119.9
C8—O5—C7	116.93 (17)	C10—C9—H9	119.9
H1S—O1S—H2S	98 (3)	O4—C10—C9	116.9 (2)
O2—N1—O1	123.7 (3)	O4—C10—C11	122.0 (2)
O2—N1—C19	118.2 (3)	C9—C10—C11	121.2 (2)
O1—N1—C19	118.0 (3)	C10—C11—C12	117.30 (19)
C15—N2—N3	120.28 (19)	C10—C11—C14	123.2 (2)
C15—N2—H2N	123 (2)	C12—C11—C14	119.5 (2)
N3—N2—H2N	117 (2)	C13—C12—C11	122.0 (2)
C14—N3—N2	115.35 (19)	C13—C12—H12	119.0
C6—C1—C2	120.0 (3)	C11—C12—H12	119.0
C6—C1—H1	120.0	C12—C13—C8	119.8 (2)
C2—C1—H1	120.0	C12—C13—H13	120.1
C3—C2—C1	120.4 (3)	C8—C13—H13	120.1
C3—C2—H2	119.8	N3—C14—C11	122.3 (2)
C1—C2—H2	119.8	N3—C14—H14	118.9
C2—C3—C4	120.3 (2)	C11—C14—H14	118.9
C2—C3—H3	119.8	O3—C15—N2	123.4 (2)
C4—C3—H3	119.8	O3—C15—C16	119.8 (2)
C3—C4—C5	119.6 (3)	N2—C15—C16	116.8 (2)
C3—C4—H4	120.2	C17—C16—C21	119.4 (2)
C5—C4—H4	120.2	C17—C16—C15	116.8 (2)
C4—C5—C6	120.6 (3)	C21—C16—C15	123.9 (2)
C4—C5—H5	119.7	C16—C17—C18	120.5 (3)
C6—C5—H5	119.7	C16—C17—H17	119.7
C1—C6—C5	119.1 (2)	C18—C17—H17	119.7
C1—C6—C7	123.3 (2)	C19—C18—C17	118.4 (2)
C5—C6—C7	117.6 (2)	C19—C18—H18	120.8
O5—C7—C6	110.37 (19)	C17—C18—H18	120.8
O5—C7—H7A	109.6	C20—C19—C18	122.5 (2)
C6—C7—H7A	109.6	C20—C19—N1	118.6 (2)
O5—C7—H7B	109.6	C18—C19—N1	118.9 (2)
C6—C7—H7B	109.6	C19—C20—C21	118.4 (2)
H7A—C7—H7B	108.1	C19—C20—H20	120.8
O5—C8—C9	124.0 (2)	C21—C20—H20	120.8
O5—C8—C13	116.4 (2)	C20—C21—C16	120.9 (2)
C9—C8—C13	119.6 (2)	C20—C21—H21	119.6
C8—C9—C10	120.1 (2)	C16—C21—H21	119.6

C15—N2—N3—C14	173.2 (2)	O5—C8—C13—C12	179.4 (2)
C6—C1—C2—C3	0.1 (5)	C9—C8—C13—C12	−0.6 (4)
C1—C2—C3—C4	−0.8 (5)	N2—N3—C14—C11	−179.85 (19)
C2—C3—C4—C5	0.7 (5)	C10—C11—C14—N3	−1.3 (3)
C3—C4—C5—C6	0.1 (4)	C12—C11—C14—N3	178.5 (2)
C2—C1—C6—C5	0.6 (4)	N3—N2—C15—O3	0.1 (4)
C2—C1—C6—C7	−179.7 (3)	N3—N2—C15—C16	−179.66 (19)
C4—C5—C6—C1	−0.7 (4)	O3—C15—C16—C17	−4.8 (4)
C4—C5—C6—C7	179.6 (2)	N2—C15—C16—C17	175.0 (2)
C8—O5—C7—C6	−177.51 (18)	O3—C15—C16—C21	174.1 (3)
C1—C6—C7—O5	2.1 (3)	N2—C15—C16—C21	−6.2 (3)
C5—C6—C7—O5	−178.1 (2)	C21—C16—C17—C18	0.3 (4)
C7—O5—C8—C9	−7.7 (3)	C15—C16—C17—C18	179.2 (2)
C7—O5—C8—C13	172.3 (2)	C16—C17—C18—C19	0.2 (4)
O5—C8—C9—C10	−179.4 (2)	C17—C18—C19—C20	−0.3 (4)
C13—C8—C9—C10	0.5 (3)	C17—C18—C19—N1	180.0 (2)
C8—C9—C10—O4	−179.2 (2)	O2—N1—C19—C20	−176.7 (3)
C8—C9—C10—C11	0.2 (3)	O1—N1—C19—C20	3.9 (4)
O4—C10—C11—C12	178.5 (2)	O2—N1—C19—C18	3.0 (4)
C9—C10—C11—C12	−0.9 (3)	O1—N1—C19—C18	−176.4 (3)
O4—C10—C11—C14	−1.6 (3)	C18—C19—C20—C21	−0.1 (4)
C9—C10—C11—C14	179.0 (2)	N1—C19—C20—C21	179.6 (2)
C10—C11—C12—C13	0.8 (3)	C19—C20—C21—C16	0.6 (4)
C14—C11—C12—C13	−179.1 (2)	C17—C16—C21—C20	−0.7 (4)
C11—C12—C13—C8	−0.1 (4)	C15—C16—C21—C20	−179.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O1Sⁱ	0.86 (2)	2.57 (4)	3.058 (3)	117 (4)
O4—H4O···N3	0.86 (2)	1.93 (3)	2.670 (2)	143 (4)
N2—H2N···O1S	0.86 (2)	2.01 (2)	2.855 (3)	166 (3)
O1S—H2S···O4ⁱⁱ	0.87 (2)	2.01 (2)	2.860 (3)	165 (4)
O1S—H1S···O3ⁱⁱⁱ	0.88 (2)	1.80 (2)	2.676 (3)	175 (5)
C14—H14···O1S	0.93	2.37	3.184 (2)	146
C21—H21···O1S	0.93	2.43	3.325 (3)	161
C7—H7B···Cg^iv	0.97	2.69	3.472 (2)	138

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇N₃O₅·H₂O
M_r	409.39
Crystal system, space group	Monoclinic, Pc
Temperature (K)	296
a, b, c (Å)	4.6275 (7), 6.5332 (11), 31.856 (5)
β (°)	92.417 (4)
V (Å³)	962.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.28 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.969, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	7388, 1713, 1663
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.088, 1.05
No. of reflections	1713
No. of parameters	288
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2010), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O1Sⁱ	0.86 (2)	2.57 (4)	3.058 (3)	117 (4)
O4—H4O···N3	0.86 (2)	1.93 (3)	2.670 (2)	143 (4)
N2—H2N···O1S	0.863 (19)	2.01 (2)	2.855 (3)	166 (3)
O1S—H2S···O4ⁱⁱ	0.873 (19)	2.01 (2)	2.860 (3)	165 (4)
O1S—H1S···O3ⁱⁱⁱ	0.88 (2)	1.80 (2)	2.676 (3)	175 (5)
C14—H14···O1S	0.9305	2.3709	3.184 (2)	146
C21—H21···O1S	0.9293	2.4331	3.325 (3)	161
C7—H7B···Cg^iv	0.97	2.69	3.472 (2)	138

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

Acknowledgements

BJ is grateful to the Council for Scientific and Industrial Research, New Delhi, India, for the award of a Senior Research Fellowship. The authors also thank the Sophisticated Analytical Instument Facility, Cochin University of Science & Technology, Kochi-22, for providing the single-crystal X-ray diffraction data.

References

Bakir, M. & Brown, O. (2002). J. Mol. Struct. 609, 129-136. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Emmanuel, J., Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o3267. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 68| Part 5| May 2012| Pages o1421-o1422

doi:10.1107/S1600536812015401

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

N′-[(E)-4-Benz­yl­oxy-2-hy­dr­oxy­benzyl­­idene]-4-nitro­benzohydrazide monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[(E)-4-Benzyloxy-2-hydroxybenzylidene]-4-nitrobenzohydrazide monohydrate