N'-[(E)-4-Benz-yloxy-2-hy-droxy-benzyl-idene]-4-nitro-benzohydrazide monohydrate.

The title compound, C(21)H(17)N(3)O(5)·H(2)O, 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 mol-ecule of solvation is present in the lattice. A conventional intra-molecular O-H⋯N hydrogen bond increases the rigidity of the mol-ecule. Inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen-bonding inter-actions establish a supra-molecular linkage among the mol-ecules in the crystal structure. There are also C-H⋯π inter-actions 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 = 409.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.088

S = 1.05

1713 reflections

288 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.16 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: 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015401/fj2537sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812015401/fj2537Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H17N3O5·H2O	F(000) = 428.0
Mr = 409.39	Dx = 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

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

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(Fo2) + (0.0687P)2 + 0.0484P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.011
1713 reflections	Δρmax = 0.14 e Å−3
288 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···Cgiv	0.97	2.69	3.472 (2)	138

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⋯Cgiv	0.97	2.69	3.472 (2)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .