2-Hydr­oxy-(2-methyl-1H-indol-3-ylmethyl­idene)benzohydrazide ethanol solvate

Yehye, W.A.; Ariffin, A.; Ng, S.W.

doi:10.1107/S1600536808011756

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o960

doi:10.1107/S1600536808011756

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2-Hydroxy-(2-methyl-1H-indol-3-ylmethylidene)benzohydrazide ethanol solvate

Wagee A. Yehye,^a Azhar Ariffin ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 April 2008; accepted 24 April 2008; online 3 May 2008)

In the title compound, C₁₇H₁₅N₃O₂·C₂H₆O, Schiff base molecules are linked by a hydroxy–amido hydrogen bond into a helical chain running along the b axis. This chain is consolidated by two other hydrogen bonds; the ethanol solvent molecule is a hydrogen-bond donor to the amide group and a hydrogen-bond acceptor for the indolyl NH group of an adjacent Schiff base molecule.

Related literature

For reports on the medicinal properties of the unsubstituted compound, indol-3-ylmethylidene-2-hydroxybenzohydrazide, see: Alemany et al. (1967 ); Fujikawa et al. (1966 ); Nakata et al. (1966 ); Singh et al. (1984 ).

Experimental

Crystal data

C₁₇H₁₅N₃O₂·C₂H₆O
M_r = 339.39
Monoclinic, P 2₁ /c
a = 7.5907 (1) Å
b = 11.2269 (2) Å
c = 20.3014 (3) Å
β = 91.924 (1)°
V = 1729.11 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.34 × 0.27 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
20827 measured reflections
3967 independent reflections
2869 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.162
S = 1.13
3967 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2ⁱ	0.84	1.76	2.594 (2)	176
O3—H3o⋯O2	0.84	2.02	2.843 (2)	165
N1—H1n⋯O1	0.88	1.91	2.618 (2)	136
N3—H3n⋯O3ⁱⁱ	0.88	1.96	2.824 (2)	168
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011756/sg2238sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011756/sg2238Isup2.hkl

checkCIF report

Comment top

There are no reports of the title Schiff base but there are several reports on the medicinal properties of the unsubstituted compound, indol-3-ylmethylidene-2-hydroxybenzohydrazide (Alemany et al., 1967; Fujikawa et al., 1966; Nakata et al., 1966; Singh et al., 1984). The methyl-substituted title compound (Scheme I, Fig. 1) is a planar molecule that is linked by a hydroxy···amido hydrogen bond into a helical chain that runs along the b-axis of the monoclinic unit cell (Fig. 2). The chain is consolidated by two other hydrogen bonds: the ethanol molecule is hydrogen-bond donor to the amido unit well as hydrogen-bond acceptor to the amino_indolyl unit of adjacent Schiff bases.

Related literature top

For reports on the medicinal properties of the unsubstituted compound, indol-3-ylmethylidene-2-hydroxybenzohydrazide, see: Alemany et al. (1967); Fujikawa et al. (1966); Nakata et al. (1966); Singh et al. (1984).

Experimental top

2-Hydroxybenzohyrazide (0.60 g, 4 mmol) and 2-methyl-1H-indole-3-carboxaldehyde (0.63 g, 4 mmol) were heated in ethanol (30 ml) for 3 h. The solvent was removed by evaporation and the light brown product recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₇H₁₅N₃O₂^.C₂H₆O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.
	Fig. 2. Hydrogen-bonded chain motif.

2-Hydroxy-(2-methyl-1H-indol-3-ylmethylidene)benzohydrazide ethanol solvate top

Crystal data top

C₁₇H₁₅N₃O₂·C₂H₆O	F(000) = 720
M_r = 339.39	D_x = 1.304 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6771 reflections
a = 7.5907 (1) Å	θ = 2.7–28.2°
b = 11.2269 (2) Å	µ = 0.09 mm⁻¹
c = 20.3014 (3) Å	T = 100 K
β = 91.924 (1)°	Prism, yellow
V = 1729.11 (5) Å³	0.34 × 0.27 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.056
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −9→9
20827 measured reflections	k = −14→14
3967 independent reflections	l = −26→22

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) = 0.162	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0721P)² + 0.9553P] where P = (F_o² + 2F_c²)/3
3967 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₇H₁₅N₃O₂·C₂H₆O	V = 1729.11 (5) Å³
M_r = 339.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5907 (1) Å	µ = 0.09 mm⁻¹
b = 11.2269 (2) Å	T = 100 K
c = 20.3014 (3) Å	0.34 × 0.27 × 0.12 mm
β = 91.924 (1)°

Data collection top

Bruker SMART APEX diffractometer	2869 reflections with I > 2σ(I)
20827 measured reflections	R_int = 0.056
3967 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.13	Δρ_max = 0.31 e Å⁻³
3967 reflections	Δρ_min = −0.30 e Å⁻³
230 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.60372 (18)	0.39960 (12)	0.26124 (6)	0.0287 (3)
H1O	0.6488	0.3342	0.2507	0.043*
O2	0.26721 (17)	0.69310 (12)	0.26809 (7)	0.0272 (3)
O3	−0.0963 (2)	0.65666 (15)	0.29094 (8)	0.0409 (4)
H3O	0.0126	0.6698	0.2916	0.061*
N1	0.3897 (2)	0.53879 (15)	0.32419 (7)	0.0255 (4)
H1N	0.4563	0.4746	0.3236	0.031*
N2	0.3081 (2)	0.57121 (15)	0.38183 (8)	0.0263 (4)
N3	0.1852 (2)	0.47451 (15)	0.59623 (8)	0.0265 (4)
H3N	0.1730	0.4372	0.6339	0.032*
C1	0.5678 (2)	0.46480 (17)	0.20605 (9)	0.0243 (4)
C2	0.6339 (3)	0.43017 (18)	0.14536 (10)	0.0283 (4)
H2	0.7025	0.3597	0.1425	0.034*
C3	0.5997 (3)	0.4978 (2)	0.08976 (10)	0.0313 (5)
H3	0.6462	0.4742	0.0489	0.038*
C4	0.4981 (3)	0.60009 (19)	0.09301 (10)	0.0311 (4)
H4	0.4760	0.6471	0.0547	0.037*
C5	0.4291 (2)	0.63320 (18)	0.15254 (9)	0.0270 (4)
H5	0.3583	0.7028	0.1545	0.032*
C6	0.4616 (2)	0.56639 (17)	0.20990 (9)	0.0233 (4)
C7	0.3674 (2)	0.60467 (17)	0.26980 (9)	0.0233 (4)
C8	0.3263 (2)	0.49282 (18)	0.42813 (9)	0.0258 (4)
H8	0.3859	0.4204	0.4194	0.031*
C9	0.2589 (2)	0.51224 (18)	0.49235 (9)	0.0258 (4)
C10	0.2617 (2)	0.42767 (18)	0.54211 (9)	0.0266 (4)
C11	0.3331 (3)	0.30424 (19)	0.54307 (10)	0.0324 (5)
H11A	0.2672	0.2556	0.5739	0.049*
H11B	0.4578	0.3060	0.5572	0.049*
H11C	0.3212	0.2698	0.4988	0.049*
C12	0.1752 (2)	0.61732 (18)	0.51780 (9)	0.0262 (4)
C13	0.1327 (3)	0.73007 (19)	0.49295 (10)	0.0304 (4)
H13	0.1621	0.7517	0.4494	0.036*
C14	0.0472 (3)	0.8094 (2)	0.53269 (11)	0.0343 (5)
H14	0.0185	0.8864	0.5161	0.041*
C15	0.0014 (3)	0.7792 (2)	0.59706 (11)	0.0359 (5)
H15	−0.0586	0.8356	0.6231	0.043*
C16	0.0425 (3)	0.66914 (19)	0.62286 (10)	0.0314 (5)
H16	0.0123	0.6483	0.6664	0.038*
C17	0.1302 (2)	0.58892 (18)	0.58288 (9)	0.0262 (4)
C18	−0.1888 (3)	0.7654 (2)	0.28171 (11)	0.0384 (5)
H18A	−0.3059	0.7584	0.3014	0.046*
H18B	−0.2077	0.7799	0.2339	0.046*
C19	−0.0926 (3)	0.8698 (2)	0.31203 (13)	0.0453 (6)
H19A	−0.1676	0.9407	0.3088	0.068*
H19B	0.0163	0.8839	0.2886	0.068*
H19C	−0.0637	0.8529	0.3585	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0333 (8)	0.0315 (7)	0.0215 (7)	0.0069 (6)	0.0051 (5)	0.0015 (6)
O2	0.0237 (7)	0.0306 (7)	0.0276 (7)	0.0012 (5)	0.0066 (5)	0.0015 (6)
O3	0.0288 (8)	0.0494 (10)	0.0452 (10)	−0.0007 (7)	0.0132 (7)	0.0105 (7)
N1	0.0239 (8)	0.0333 (9)	0.0198 (8)	0.0029 (7)	0.0060 (6)	−0.0004 (7)
N2	0.0214 (8)	0.0376 (9)	0.0202 (8)	−0.0009 (7)	0.0053 (6)	−0.0021 (7)
N3	0.0232 (8)	0.0368 (9)	0.0197 (8)	−0.0011 (7)	0.0043 (6)	0.0004 (7)
C1	0.0210 (9)	0.0310 (10)	0.0209 (9)	−0.0029 (7)	0.0021 (7)	0.0010 (7)
C2	0.0244 (9)	0.0346 (10)	0.0260 (10)	0.0019 (8)	0.0041 (7)	−0.0026 (8)
C3	0.0292 (10)	0.0440 (12)	0.0211 (10)	−0.0011 (9)	0.0062 (8)	−0.0014 (8)
C4	0.0327 (10)	0.0399 (11)	0.0208 (9)	−0.0021 (9)	0.0019 (8)	0.0045 (8)
C5	0.0251 (9)	0.0308 (10)	0.0252 (10)	−0.0008 (8)	0.0021 (7)	0.0016 (8)
C6	0.0194 (8)	0.0302 (10)	0.0205 (9)	−0.0040 (7)	0.0028 (7)	−0.0016 (7)
C7	0.0185 (8)	0.0279 (9)	0.0236 (9)	−0.0039 (7)	0.0016 (7)	−0.0004 (7)
C8	0.0192 (9)	0.0341 (10)	0.0242 (10)	−0.0012 (7)	0.0029 (7)	−0.0017 (8)
C9	0.0173 (8)	0.0379 (11)	0.0224 (9)	−0.0022 (7)	0.0018 (7)	−0.0010 (8)
C10	0.0184 (8)	0.0391 (11)	0.0224 (9)	−0.0029 (8)	0.0034 (7)	−0.0018 (8)
C11	0.0308 (10)	0.0400 (11)	0.0268 (10)	−0.0006 (9)	0.0069 (8)	0.0005 (9)
C12	0.0167 (8)	0.0396 (11)	0.0225 (9)	−0.0030 (8)	0.0022 (7)	−0.0026 (8)
C13	0.0222 (9)	0.0410 (11)	0.0279 (10)	−0.0020 (8)	0.0021 (7)	0.0017 (9)
C14	0.0264 (10)	0.0362 (11)	0.0402 (12)	0.0025 (9)	−0.0012 (9)	0.0009 (9)
C15	0.0280 (10)	0.0450 (12)	0.0349 (11)	0.0038 (9)	0.0026 (8)	−0.0087 (10)
C16	0.0238 (9)	0.0447 (12)	0.0258 (10)	−0.0009 (8)	0.0042 (8)	−0.0055 (9)
C17	0.0177 (8)	0.0382 (11)	0.0226 (9)	−0.0032 (7)	0.0012 (7)	−0.0020 (8)
C18	0.0253 (10)	0.0568 (14)	0.0332 (11)	0.0033 (10)	0.0047 (8)	0.0130 (10)
C19	0.0292 (11)	0.0548 (15)	0.0520 (15)	0.0108 (10)	0.0026 (10)	0.0041 (12)

Geometric parameters (Å, º) top

O1—C1	1.358 (2)	C8—H8	0.9500
O1—H1O	0.8400	C9—C10	1.386 (3)
O2—C7	1.250 (2)	C9—C12	1.444 (3)
O3—C18	1.417 (3)	C10—C11	1.488 (3)
O3—H3O	0.8400	C11—H11A	0.9800
N1—C7	1.335 (2)	C11—H11B	0.9800
N1—N2	1.391 (2)	C11—H11C	0.9800
N1—H1N	0.8800	C12—C13	1.396 (3)
N2—C8	1.292 (3)	C12—C17	1.412 (3)
N3—C10	1.365 (2)	C13—C14	1.379 (3)
N3—C17	1.375 (3)	C13—H13	0.9500
N3—H3N	0.8800	C14—C15	1.405 (3)
C1—C6	1.401 (3)	C14—H14	0.9500
C1—C2	1.401 (3)	C15—C16	1.374 (3)
C2—C3	1.378 (3)	C15—H15	0.9500
C2—H2	0.9500	C16—C17	1.396 (3)
C3—C4	1.386 (3)	C16—H16	0.9500
C3—H3	0.9500	C18—C19	1.502 (4)
C4—C5	1.384 (3)	C18—H18A	0.9900
C4—H4	0.9500	C18—H18B	0.9900
C5—C6	1.400 (3)	C19—H19A	0.9800
C5—H5	0.9500	C19—H19B	0.9800
C6—C7	1.494 (3)	C19—H19C	0.9800
C8—C9	1.433 (3)

C1—O1—H1O	109.5	C9—C10—C11	130.10 (18)
C18—O3—H3O	109.5	C10—C11—H11A	109.5
C7—N1—N2	120.20 (16)	C10—C11—H11B	109.5
C7—N1—H1N	119.9	H11A—C11—H11B	109.5
N2—N1—H1N	119.9	C10—C11—H11C	109.5
C8—N2—N1	113.21 (16)	H11A—C11—H11C	109.5
C10—N3—C17	109.62 (16)	H11B—C11—H11C	109.5
C10—N3—H3N	125.2	C13—C12—C17	118.84 (18)
C17—N3—H3N	125.2	C13—C12—C9	135.28 (18)
O1—C1—C6	119.52 (16)	C17—C12—C9	105.88 (17)
O1—C1—C2	120.54 (17)	C14—C13—C12	118.82 (19)
C6—C1—C2	119.93 (17)	C14—C13—H13	120.6
C3—C2—C1	120.29 (19)	C12—C13—H13	120.6
C3—C2—H2	119.9	C13—C14—C15	121.6 (2)
C1—C2—H2	119.9	C13—C14—H14	119.2
C2—C3—C4	120.49 (19)	C15—C14—H14	119.2
C2—C3—H3	119.8	C16—C15—C14	120.8 (2)
C4—C3—H3	119.8	C16—C15—H15	119.6
C5—C4—C3	119.45 (19)	C14—C15—H15	119.6
C5—C4—H4	120.3	C15—C16—C17	117.72 (19)
C3—C4—H4	120.3	C15—C16—H16	121.1
C4—C5—C6	121.42 (19)	C17—C16—H16	121.1
C4—C5—H5	119.3	N3—C17—C16	129.46 (18)
C6—C5—H5	119.3	N3—C17—C12	108.30 (17)
C5—C6—C1	118.38 (17)	C16—C17—C12	122.23 (19)
C5—C6—C7	116.57 (17)	O3—C18—C19	112.73 (18)
C1—C6—C7	124.88 (17)	O3—C18—H18A	109.0
O2—C7—N1	121.54 (17)	C19—C18—H18A	109.0
O2—C7—C6	120.86 (17)	O3—C18—H18B	109.0
N1—C7—C6	117.57 (16)	C19—C18—H18B	109.0
N2—C8—C9	121.71 (18)	H18A—C18—H18B	107.8
N2—C8—H8	119.1	C18—C19—H19A	109.5
C9—C8—H8	119.1	C18—C19—H19B	109.5
C10—C9—C8	124.18 (18)	H19A—C19—H19B	109.5
C10—C9—C12	107.16 (17)	C18—C19—H19C	109.5
C8—C9—C12	128.66 (18)	H19A—C19—H19C	109.5
N3—C10—C9	109.04 (18)	H19B—C19—H19C	109.5
N3—C10—C11	120.86 (17)

C7—N1—N2—C8	173.12 (16)	C17—N3—C10—C11	−179.95 (17)
O1—C1—C2—C3	−178.81 (17)	C8—C9—C10—N3	−179.13 (17)
C6—C1—C2—C3	2.2 (3)	C12—C9—C10—N3	−0.1 (2)
C1—C2—C3—C4	−0.7 (3)	C8—C9—C10—C11	1.4 (3)
C2—C3—C4—C5	−0.8 (3)	C12—C9—C10—C11	−179.53 (19)
C3—C4—C5—C6	0.8 (3)	C10—C9—C12—C13	−179.7 (2)
C4—C5—C6—C1	0.6 (3)	C8—C9—C12—C13	−0.7 (4)
C4—C5—C6—C7	−174.79 (17)	C10—C9—C12—C17	−0.4 (2)
O1—C1—C6—C5	178.89 (16)	C8—C9—C12—C17	178.61 (18)
C2—C1—C6—C5	−2.1 (3)	C17—C12—C13—C14	−0.4 (3)
O1—C1—C6—C7	−6.1 (3)	C9—C12—C13—C14	178.8 (2)
C2—C1—C6—C7	172.88 (17)	C12—C13—C14—C15	−0.3 (3)
N2—N1—C7—O2	−3.4 (3)	C13—C14—C15—C16	0.7 (3)
N2—N1—C7—C6	178.81 (15)	C14—C15—C16—C17	−0.2 (3)
C5—C6—C7—O2	−1.0 (3)	C10—N3—C17—C16	178.45 (19)
C1—C6—C7—O2	−176.05 (17)	C10—N3—C17—C12	−0.8 (2)
C5—C6—C7—N1	176.83 (16)	C15—C16—C17—N3	−179.69 (19)
C1—C6—C7—N1	1.8 (3)	C15—C16—C17—C12	−0.5 (3)
N1—N2—C8—C9	176.97 (16)	C13—C12—C17—N3	−179.82 (16)
N2—C8—C9—C10	174.44 (18)	C9—C12—C17—N3	0.7 (2)
N2—C8—C9—C12	−4.4 (3)	C13—C12—C17—C16	0.9 (3)
C17—N3—C10—C9	0.5 (2)	C9—C12—C17—C16	−178.58 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.84	1.76	2.594 (2)	176
O3—H3o···O2	0.84	2.02	2.843 (2)	165
N1—H1n···O1	0.88	1.91	2.618 (2)	136
N3—H3n···O3ⁱⁱ	0.88	1.96	2.824 (2)	168

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₃O₂·C₂H₆O
M_r	339.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.5907 (1), 11.2269 (2), 20.3014 (3)
β (°)	91.924 (1)
V (Å³)	1729.11 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.34 × 0.27 × 0.12

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20827, 3967, 2869
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.162, 1.13
No. of reflections	3967
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.30

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.84	1.76	2.594 (2)	176
O3—H3o···O2	0.84	2.02	2.843 (2)	165
N1—H1n···O1	0.88	1.91	2.618 (2)	136
N3—H3n···O3ⁱⁱ	0.88	1.96	2.824 (2)	168

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

Acknowledgements

We acknowledge the SAGA grant (06–02-03–0147) for support of this study, and the University of Malaya for the purchase of the diffractometer.

References

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