(E)-4-Meth­oxy-N′-[(pyridin-4-yl)methyl­idene]benzohydrazide monohydrate

Taha, M.; Naz, H.; Rahman, A.A.; Ismail, N.H.; Sammer, Y.

doi:10.1107/S1600536812034988

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2778

doi:10.1107/S1600536812034988

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(E)-4-Methoxy-N′-[(pyridin-4-yl)methylidene]benzohydrazide monohydrate

Muhammad Taha,^a Humera Naz,^a,^b Aqilah Abd Rahman,^a,^b Nor Hadiani Ismail ^a and Yousuf Sammer ^c ^*

^aAtta-ur-Rahman Research Institute for Natural Products Discovery (RiND), Universiti Tecknologi MARA, Puncak Alam, 42300 Selangor, Malaysia, ^bFaculty of Pharmacy, Universiti Tecknologi MARA, Puncak Alam, 42300 Selangor, Malaysia, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 6 August 2012; accepted 8 August 2012; online 25 August 2012)

In the title compound, C₁₄H₁₃N₃O₂·H₂O, the azomethine double bond adopts an E conformation and the N—N=C—C torsion angle is 178.37 (19)°. The dihedral angle between the benzene and pyridine rings is 5.58 (12)° and the C atom of the methoxy group is roughly coplanar with its attached ring [deviation = 0.157 (3) Å]. In the crystal, the components are linked by O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds, forming (001) sheets. The water O atom accepts one N—H⋯O and two C—H⋯O interactions from the adjacent organic molecule.

Related literature

For the biological activity of benzohydraazides, see: Bayrak et al. (2009 ). For the crystal structures of related benzohydrazides, see: Taha et al. (2012); Fun et al. (2011 ); Lu et al. (2009 ); Zhang (2009a ,b ).

Experimental

Crystal data

C₁₄H₁₃N₃O₂·H₂O
M_r = 273.29
Monoclinic, P 2₁ /c
a = 6.6878 (5) Å
b = 7.0420 (5) Å
c = 29.249 (2) Å
β = 94.233 (2)°
V = 1373.74 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.20 × 0.17 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.981, T_max = 0.991
7767 measured reflections
2560 independent reflections
1548 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.146
S = 1.03
2560 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O1ⁱ	0.84	2.00	2.811 (2)	162
O1W—H2⋯N3ⁱⁱ	0.91	2.11	2.956 (3)	154
N1—H1A⋯O1W	0.86	2.08	2.911 (2)	161
C1—H1B⋯O1W	0.93	2.54	3.440 (3)	162
C8—H8A⋯O1W	0.93	2.48	3.272 (3)	143
C11—H11A⋯O2ⁱⁱⁱ	0.93	2.47	3.375 (3)	165
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034988/hb6930sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034988/hb6930Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034988/hb6930Isup3.cml

checkCIF report

Comment top

The diverse structural features and wide range of biological activities make Benzohydrazides as an importent class of organic compounds. The title compound is an structure analogue of Benzohydrazide, synthesize as a part of our ongoing research to study their varoius biological activities. The structure of title compound (Fig. 1) is similar to that of our recently published benzohydrazide derivative (E)-N'-(3,4-Dimethoxybenzylidene)-4-methoxybenzohydrazide (Taha et al., 2012, Pv2573) with the difference that 3,4-dimethoxy phenyl ring is replaced by pyridine ring (N3/C9–C13). The azomethine (C=N,1.269 (3) Å) double bond adopt an E conformation (Fig. 1) with the torsion angle of 178.3 (19)° (N1–N2–C8–C9). Phenyl and pyridine rings (C1–C6 and N3/C9–C13) have a dihedral angle of 5.58 (12)° between them and maximum deviation of 0.006 (3) Å for C13 atoms from the root mean square plane. The bond lengths and angle were found to be similar as in structurally realted compounds (Fun et al., 2011, Lu et al., 2009, Zhang et al., 2009). In the crystal structure molecules are consolidated by C11—H11A···O2 intermolecular hydrogen bonds (Fig.2) and extended to form a two-dimensional-network due to O1W—H1···O1 and O1W—H2···N3 (symmetry codes as in Table 2) intermolecular linkages made by water solvates (Fig. 2).

Related literature top

For the biological activity of benzohydraazides, see: Bayrak et al. (2009). For the crystal structures of related benzohydrazides, see: Taha et al. (2012); Fun et al. (2011); Lu et al. (2009); Zhang (2009a,b).

Experimental top

A mixture of 2 mmol of 4-methoxybenzohydrazide (0.332 g), 2 mmol isonicotinaldehyde (0.214 g) and catalytical amount of acetic acid was refluxed in methanol (20 ml) for 3 h. The progress of reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated by vacuum to afford the crude product, which was dissolved and recrystallized from methanol to obtain colourless blocks (0.418 g in 82% yield).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 30% probability level.

Fig. 2. The crystal packing of the title compound I. Only hydrogen atoms involved in hydrogen bonding are shown.

(E)-4-Methoxy-N'-[(pyridin-4-yl)methylidene]benzohydrazide monohydrate top

Crystal data top

C₁₄H₁₃N₃O₂·H₂O	F(000) = 576
M_r = 273.29	D_x = 1.321 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6878 (5) Å	Cell parameters from 1112 reflections
b = 7.0420 (5) Å	θ = 2.8–22.8°
c = 29.249 (2) Å	µ = 0.10 mm⁻¹
β = 94.233 (2)°	T = 273 K
V = 1373.74 (17) Å³	Block, colourless
Z = 4	0.20 × 0.17 × 0.10 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2560 independent reflections
Radiation source: fine-focus sealed tube	1548 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scan	θ_max = 25.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
T_min = 0.981, T_max = 0.991	k = −7→8
7767 measured reflections	l = −35→35

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.070P)²] where P = (F_o² + 2F_c²)/3
2560 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₁₃N₃O₂·H₂O	V = 1373.74 (17) Å³
M_r = 273.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.6878 (5) Å	µ = 0.10 mm⁻¹
b = 7.0420 (5) Å	T = 273 K
c = 29.249 (2) Å	0.20 × 0.17 × 0.10 mm
β = 94.233 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	2560 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1548 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.991	R_int = 0.038
7767 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	Δρ_max = 0.16 e Å⁻³
2560 reflections	Δρ_min = −0.20 e Å⁻³
182 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	0.0974 (2)	0.3345 (3)	0.05572 (5)	0.0607 (6)
O2	0.6325 (2)	0.1818 (3)	−0.10876 (5)	0.0590 (5)
N1	0.3945 (3)	0.3260 (3)	0.09758 (6)	0.0446 (5)
H1A	0.5220	0.3083	0.0985	0.053*
N2	0.3018 (3)	0.3646 (3)	0.13646 (6)	0.0436 (5)
N3	0.1587 (4)	0.5223 (4)	0.29858 (7)	0.0662 (7)
C1	0.5874 (3)	0.2320 (3)	0.01504 (7)	0.0413 (6)
H1B	0.6640	0.2206	0.0428	0.050*
C2	0.6754 (3)	0.1988 (3)	−0.02547 (7)	0.0424 (6)
H2A	0.8102	0.1659	−0.0250	0.051*
C3	0.5623 (3)	0.2146 (3)	−0.06665 (7)	0.0424 (6)
C4	0.3619 (3)	0.2658 (4)	−0.06705 (8)	0.0513 (7)
H4A	0.2858	0.2773	−0.0948	0.062*
C5	0.2756 (3)	0.2993 (3)	−0.02691 (8)	0.0462 (6)
H5A	0.1412	0.3340	−0.0277	0.055*
C6	0.3867 (3)	0.2821 (3)	0.01516 (7)	0.0380 (5)
C7	0.2800 (3)	0.3160 (3)	0.05702 (7)	0.0411 (6)
C8	0.4126 (4)	0.3827 (4)	0.17334 (7)	0.0469 (6)
H8A	0.5506	0.3663	0.1732	0.056*
C9	0.3230 (3)	0.4292 (3)	0.21603 (7)	0.0429 (6)
C10	0.4319 (4)	0.4088 (4)	0.25789 (8)	0.0544 (7)
H10A	0.5630	0.3639	0.2592	0.065*
C11	0.3438 (5)	0.4556 (4)	0.29754 (9)	0.0650 (8)
H11A	0.4189	0.4395	0.3253	0.078*
C12	0.0554 (4)	0.5413 (4)	0.25821 (9)	0.0580 (7)
H12A	−0.0747	0.5880	0.2580	0.070*
C13	0.1279 (4)	0.4965 (4)	0.21676 (8)	0.0499 (6)
H13A	0.0476	0.5110	0.1896	0.060*
C14	0.8422 (4)	0.1550 (5)	−0.11117 (9)	0.0640 (8)
H14A	0.8706	0.1333	−0.1424	0.096*
H14B	0.8852	0.0473	−0.0929	0.096*
H14C	0.9124	0.2663	−0.0998	0.096*
O1W	0.8218 (2)	0.2877 (3)	0.12291 (5)	0.0657 (6)
H1	0.9224	0.2994	0.1078	0.098*
H2	0.8700	0.2103	0.1461	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0361 (10)	0.1027 (16)	0.0440 (10)	0.0027 (10)	0.0085 (7)	0.0049 (9)
O2	0.0496 (10)	0.0914 (15)	0.0373 (9)	−0.0042 (10)	0.0115 (8)	−0.0133 (9)
N1	0.0347 (10)	0.0645 (15)	0.0357 (11)	0.0026 (10)	0.0104 (8)	0.0015 (9)
N2	0.0415 (11)	0.0552 (13)	0.0352 (11)	0.0018 (10)	0.0111 (9)	0.0016 (9)
N3	0.0749 (17)	0.0805 (18)	0.0450 (14)	−0.0011 (14)	0.0167 (12)	−0.0098 (12)
C1	0.0384 (13)	0.0493 (15)	0.0358 (12)	0.0007 (11)	0.0012 (10)	0.0032 (10)
C2	0.0360 (13)	0.0508 (16)	0.0410 (13)	0.0012 (11)	0.0057 (10)	−0.0028 (11)
C3	0.0419 (13)	0.0485 (15)	0.0378 (13)	−0.0085 (11)	0.0102 (10)	−0.0054 (11)
C4	0.0428 (14)	0.075 (2)	0.0359 (14)	−0.0049 (13)	−0.0009 (10)	−0.0017 (12)
C5	0.0340 (13)	0.0624 (18)	0.0424 (14)	−0.0034 (12)	0.0034 (10)	0.0007 (12)
C6	0.0378 (12)	0.0403 (14)	0.0366 (12)	−0.0053 (11)	0.0068 (9)	0.0025 (10)
C7	0.0370 (13)	0.0488 (16)	0.0379 (13)	−0.0027 (11)	0.0057 (10)	0.0049 (11)
C8	0.0394 (13)	0.0605 (17)	0.0416 (14)	0.0046 (12)	0.0084 (11)	0.0005 (12)
C9	0.0454 (14)	0.0469 (16)	0.0370 (13)	−0.0016 (12)	0.0074 (10)	0.0001 (11)
C10	0.0537 (15)	0.0636 (19)	0.0456 (15)	0.0042 (14)	0.0016 (11)	−0.0006 (13)
C11	0.081 (2)	0.077 (2)	0.0368 (15)	0.0004 (17)	0.0010 (13)	−0.0006 (13)
C12	0.0553 (16)	0.0642 (19)	0.0560 (17)	−0.0004 (14)	0.0137 (13)	−0.0108 (14)
C13	0.0504 (15)	0.0574 (17)	0.0423 (14)	0.0025 (13)	0.0059 (11)	−0.0048 (12)
C14	0.0565 (17)	0.087 (2)	0.0516 (16)	0.0062 (16)	0.0226 (13)	−0.0059 (14)
O1W	0.0371 (9)	0.1143 (17)	0.0465 (10)	0.0079 (10)	0.0095 (7)	0.0166 (10)

Geometric parameters (Å, º) top

O1—C7	1.226 (2)	C5—H5A	0.9300
O2—C3	1.370 (3)	C6—C7	1.481 (3)
O2—C14	1.422 (3)	C8—C9	1.462 (3)
N1—N2	1.362 (2)	C8—H8A	0.9300
N1—C7	1.365 (3)	C9—C10	1.385 (3)
N1—H1A	0.8600	C9—C13	1.390 (3)
N2—C8	1.269 (3)	C10—C11	1.379 (3)
N3—C11	1.326 (3)	C10—H10A	0.9300
N3—C12	1.330 (3)	C11—H11A	0.9300
C1—C2	1.382 (3)	C12—C13	1.375 (3)
C1—C6	1.388 (3)	C12—H12A	0.9300
C1—H1B	0.9300	C13—H13A	0.9300
C2—C3	1.379 (3)	C14—H14A	0.9600
C2—H2A	0.9300	C14—H14B	0.9600
C3—C4	1.387 (3)	C14—H14C	0.9600
C4—C5	1.367 (3)	O1W—H1	0.8361
C4—H4A	0.9300	O1W—H2	0.9098
C5—C6	1.395 (3)

C3—O2—C14	118.14 (18)	N1—C7—C6	116.9 (2)
N2—N1—C7	118.33 (18)	N2—C8—C9	119.9 (2)
N2—N1—H1A	120.8	N2—C8—H8A	120.1
C7—N1—H1A	120.8	C9—C8—H8A	120.1
C8—N2—N1	117.12 (19)	C10—C9—C13	117.0 (2)
C11—N3—C12	116.1 (2)	C10—C9—C8	120.7 (2)
C2—C1—C6	121.2 (2)	C13—C9—C8	122.3 (2)
C2—C1—H1B	119.4	C11—C10—C9	119.3 (2)
C6—C1—H1B	119.4	C11—C10—H10A	120.3
C3—C2—C1	119.6 (2)	C9—C10—H10A	120.3
C3—C2—H2A	120.2	N3—C11—C10	124.1 (3)
C1—C2—H2A	120.2	N3—C11—H11A	117.9
O2—C3—C2	124.7 (2)	C10—C11—H11A	117.9
O2—C3—C4	115.6 (2)	N3—C12—C13	124.5 (3)
C2—C3—C4	119.7 (2)	N3—C12—H12A	117.8
C5—C4—C3	120.5 (2)	C13—C12—H12A	117.8
C5—C4—H4A	119.8	C12—C13—C9	119.0 (2)
C3—C4—H4A	119.8	C12—C13—H13A	120.5
C4—C5—C6	120.8 (2)	C9—C13—H13A	120.5
C4—C5—H5A	119.6	O2—C14—H14A	109.5
C6—C5—H5A	119.6	O2—C14—H14B	109.5
C1—C6—C5	118.2 (2)	H14A—C14—H14B	109.5
C1—C6—C7	124.6 (2)	O2—C14—H14C	109.5
C5—C6—C7	117.2 (2)	H14A—C14—H14C	109.5
O1—C7—N1	121.0 (2)	H14B—C14—H14C	109.5
O1—C7—C6	122.1 (2)	H1—O1W—H2	101.5

C7—N1—N2—C8	−176.5 (2)	C1—C6—C7—O1	−169.8 (2)
C6—C1—C2—C3	−0.3 (3)	C5—C6—C7—O1	9.2 (3)
C14—O2—C3—C2	−9.1 (3)	C1—C6—C7—N1	10.1 (3)
C14—O2—C3—C4	171.4 (2)	C5—C6—C7—N1	−170.9 (2)
C1—C2—C3—O2	−178.8 (2)	N1—N2—C8—C9	178.37 (19)
C1—C2—C3—C4	0.7 (4)	N2—C8—C9—C10	165.7 (2)
O2—C3—C4—C5	179.1 (2)	N2—C8—C9—C13	−14.8 (4)
C2—C3—C4—C5	−0.4 (4)	C13—C9—C10—C11	−0.2 (4)
C3—C4—C5—C6	−0.3 (4)	C8—C9—C10—C11	179.4 (2)
C2—C1—C6—C5	−0.4 (3)	C12—N3—C11—C10	0.8 (4)
C2—C1—C6—C7	178.6 (2)	C9—C10—C11—N3	−0.7 (4)
C4—C5—C6—C1	0.7 (4)	C11—N3—C12—C13	0.1 (4)
C4—C5—C6—C7	−178.4 (2)	N3—C12—C13—C9	−1.0 (4)
N2—N1—C7—O1	−2.6 (3)	C10—C9—C13—C12	1.0 (4)
N2—N1—C7—C6	177.42 (18)	C8—C9—C13—C12	−178.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O1ⁱ	0.84	2.00	2.811 (2)	162
O1W—H2···N3ⁱⁱ	0.91	2.11	2.956 (3)	154
N1—H1A···O1W	0.86	2.08	2.911 (2)	161
C1—H1B···O1W	0.93	2.54	3.440 (3)	162
C8—H8A···O1W	0.93	2.48	3.272 (3)	143
C11—H11A···O2ⁱⁱⁱ	0.93	2.47	3.375 (3)	165

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₃O₂·H₂O
M_r	273.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	6.6878 (5), 7.0420 (5), 29.249 (2)
β (°)	94.233 (2)
V (Å³)	1373.74 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.17 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.981, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	7767, 2560, 1548
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.146, 1.03
No. of reflections	2560
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O1ⁱ	0.84	2.00	2.811 (2)	162
O1W—H2···N3ⁱⁱ	0.91	2.11	2.956 (3)	154
N1—H1A···O1W	0.86	2.08	2.911 (2)	161
C1—H1B···O1W	0.93	2.54	3.440 (3)	162
C8—H8A···O1W	0.93	2.48	3.272 (3)	143
C11—H11A···O2ⁱⁱⁱ	0.93	2.47	3.375 (3)	165

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

References

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Volume 68| Part 9| September 2012| Page o2778

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