1,2-Bis[1-(3-methyl­sulfanyl-1,2,4-triazin-5-yl)ethyl­idene]diazane

Mojzych, M.; Karczmarzyk, Z.; Urbańczyk-Lipkowska, Z.; Kalicki, P.

doi:10.1107/S1600536809025033

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1772

doi:10.1107/S1600536809025033

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1,2-Bis[1-(3-methylsulfanyl-1,2,4-triazin-5-yl)ethylidene]diazane

Mariusz Mojzych,^a ^* Zbigniew Karczmarzyk,^a Zofia Urbańczyk-Lipkowska ^b and Przemysław Kalicki ^b

^aDepartment of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland, and ^bInstitute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw 42, POB 58, Poland
^*Correspondence e-mail: mojzych@ap.siedlce.pl

(Received 9 June 2009; accepted 29 June 2009; online 4 July 2009)

The molecule of the title compound, C₁₂H₁₄N₈S₂, has an N—N gauche conformation. The triazine rings are nearly coplanar with respect to the imide bonds [C—C—C—N torsion angles = −15.3 (3) and −15.8 (3)°] and they are twisted by 77.88 (7)°. The overall conformation of the molecule is stabilized by intramolecular C—H⋯N hydrogen bonding. The molecular packing is influenced by π–π interactions of the triazine systems with a shortest centroid–centroid separation of 3.5242 (12) Å.

Related literature

For the biological activity of hydrazones, see: Rollas et al. (2002 ); Terzioglu & Gürsoy (2003 ); Bedia et al. (2006 ). For the synthesis, see: Karczmarzyk et al. (2000 ); Rykowski et al. (2000 ); Mojzych & Rykowski (2003 ). For related structures, see: Lewis et al. (2000 ); Sauro & Workentin (2001 ); Tai et al. (2008 ).

Experimental

Crystal data

C₁₂H₁₄N₈S₂
M_r = 334.43
Monoclinic, P 2₁ /c
a = 14.4962 (4) Å
b = 7.0814 (2) Å
c = 15.6619 (5) Å
β = 107.465 (2)°
V = 1533.63 (8) Å³
Z = 4
Cu Kα radiation
μ = 3.24 mm⁻¹
T = 293 K
0.32 × 0.22 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.474, T_max = 0.753
5750 measured reflections
2635 independent reflections
2200 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.117
S = 1.03
2635 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.23 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
C19—H193⋯N4	0.96	2.48	2.875 (3)	104
C20—H202⋯N8	0.96	2.46	2.816 (3)	101

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025033/kp2223sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025033/kp2223Isup2.hkl

checkCIF report

Comment top

Hydrazones have been found to possess antimicrobial, anticonvulsant, analgesic, antiinflammatory, antiplatelet, antitubercular, anticancer and antitumoral activities (Rollas et al., 2002; Terzioglu & Gürsoy, 2003; Bedia et al., 2006). Recently, we reported several aryl hydrazones of 5-acyl-1,2,4-triazine as important building blocks for the synthesis of N-1 substituted pyrazolo[4,3-e][1,2,4]triazines (Karczmarzyk et al., 2000; Rykowski et al., 2000). In continuation of work in this area we report herein the crystal structure of the title compound as intermediate for the construction of N-1 unsubstituted pyrazolo[4,3-e][1,2,4]triazines (Mojzych & Rykowski, 2003) and as a ligand for the synthesis of novel organometallic compounds with expected biological activity and other material applications (Sauro & Workentin, 2001).

In the title molecule, the C—N imide bonds of 1.283 (3) and 1.279 (3) Å and N—N hydrazine bond of 1.370 (2) Å are very similar to those reported for other related structures (Lewis et al., 2000; Tai et al., 2008). The molecule of (I) has an N—N gauche conformation with C7—N8—N9—C10 torsion angle of 114.8 (2)°. The triazine rings are nearly coplanar with the respective imide bonds [C6—C5—C7—N8 = -15.3 (3)° and C16—-C15—C10—N9 = -15.8 (3)°] and they are twisted by 77.88 (7)° with respect to each other. This conformation is stabilized by the intramolecular C19—H193···N4 and C20—H202···N8 hydrogen bonds (Table 1). The methylsulfanyl groups are in different conformations in respect to the mother triazine rings with the torsion angles N4—C3—S17—C18 and N14—C13—S21—C22 of 179.03 (15) and 7.0 (2)°, respectively. Significant π-π interactions are observed in the packing (Spek, 2009). The triazine N1···C6 rings form molecular stacks in the [010] direction with centroid-to-centroid separations of 3.5242 (12) (1 - x, -y, 1 - z) and 3.6473 (12) Å (1 - x, 1 - y, 1 - z) (Fig. 2) and slippages of 0.898 and 1.615 Å, respectively.

Related literature top

For the biological activity of hydrazones, see: Rollas et al. (2002); Terzioglu & Gürsoy (2003); Bedia et al. (2006). For the synthesis, see: Karczmarzyk et al. (2000); Rykowski et al. (2000); Mojzych & Rykowski (2003). For related structures, see: Lewis et al. (2000); Sauro & Workentin (2001); Tai et al. (2008).

Experimental top

The synthesis of compound (I) and its analytical data (IR, ¹H NMR) were described by Mojzych & Rykowski (2003). Crystals suitable for X-ray diffraction analysis were grown by slow evaporation of an ethanol solution.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with atom labels and the 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A view of part of the crystal structure of (I) along (a) [100] and (b) [010], showing the formation of a column of stacked triazine rings.

1,2-Bis[1-(3-methylsulfanyl-1,2,4-triazin-5-yl)ethylidene]diazane top

Crystal data top

C₁₂H₁₄N₈S₂	F(000) = 696
M_r = 334.43	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1791 reflections
a = 14.4962 (4) Å	θ = 5.8–66.9°
b = 7.0814 (2) Å	µ = 3.24 mm⁻¹
c = 15.6619 (5) Å	T = 293 K
β = 107.465 (2)°	Plate, yellow
V = 1533.63 (8) Å³	0.32 × 0.22 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2635 independent reflections
Radiation source: fine-focus sealed tube	2200 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 67.7°, θ_min = 5.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
T_min = 0.474, T_max = 0.753	k = −8→2
5750 measured reflections	l = −18→17

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0575P)² + 0.4463P] where P = (F_o² + 2F_c²)/3
2635 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₂H₁₄N₈S₂	V = 1533.63 (8) Å³
M_r = 334.43	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 14.4962 (4) Å	µ = 3.24 mm⁻¹
b = 7.0814 (2) Å	T = 293 K
c = 15.6619 (5) Å	0.32 × 0.22 × 0.08 mm
β = 107.465 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2635 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2200 reflections with I > 2σ(I)
T_min = 0.474, T_max = 0.753	R_int = 0.035
5750 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
2635 reflections	Δρ_min = −0.23 e Å⁻³
199 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
S17	0.29719 (4)	0.25053 (8)	0.43807 (4)	0.0484 (2)
S21	0.94963 (5)	0.20147 (9)	0.04349 (4)	0.0524 (2)
N1	0.56957 (14)	0.2978 (3)	0.57615 (13)	0.0434 (4)
N2	0.47200 (14)	0.3040 (3)	0.55353 (12)	0.0416 (4)
N4	0.46056 (13)	0.1897 (2)	0.40671 (11)	0.0369 (4)
N8	0.69264 (14)	0.1583 (3)	0.38213 (12)	0.0430 (4)
N9	0.74256 (14)	0.0796 (3)	0.32936 (13)	0.0437 (5)
N11	0.92948 (16)	−0.1765 (3)	0.21425 (15)	0.0530 (5)
N12	0.95071 (15)	−0.0836 (3)	0.14810 (14)	0.0513 (5)
N14	0.86038 (13)	0.1842 (2)	0.17013 (12)	0.0391 (4)
C3	0.42339 (16)	0.2505 (3)	0.47130 (15)	0.0365 (5)
C5	0.55527 (16)	0.1885 (3)	0.42894 (14)	0.0346 (5)
C6	0.61047 (17)	0.2431 (3)	0.51602 (15)	0.0384 (5)
H61	0.6776	0.2403	0.5312	0.058*
C7	0.60199 (16)	0.1214 (3)	0.36205 (14)	0.0373 (5)
C10	0.77872 (16)	0.1880 (3)	0.28245 (14)	0.0399 (5)
C13	0.91659 (16)	0.0920 (3)	0.13019 (15)	0.0410 (5)
C15	0.83999 (15)	0.0913 (3)	0.23536 (14)	0.0374 (5)
C16	0.87630 (17)	−0.0913 (3)	0.25750 (16)	0.0476 (6)
H161	0.8624	−0.1544	0.3042	0.071*
C18	0.27045 (19)	0.3325 (3)	0.53668 (18)	0.0524 (6)
H181	0.2921	0.2408	0.5836	0.079*
H182	0.2019	0.3504	0.5235	0.079*
H183	0.3030	0.4502	0.5557	0.079*
C19	0.54418 (18)	0.0180 (3)	0.28090 (15)	0.0470 (6)
H191	0.5800	−0.0897	0.2712	0.071*
H192	0.5309	0.1002	0.2299	0.071*
H193	0.4844	−0.0232	0.2892	0.071*
C20	0.7638 (2)	0.3954 (3)	0.27192 (19)	0.0583 (7)
H201	0.8222	0.4541	0.2681	0.087*
H202	0.7476	0.4451	0.3226	0.087*
H203	0.7122	0.4211	0.2183	0.087*
C22	0.9029 (2)	0.4349 (4)	0.04713 (18)	0.0561 (6)
H221	0.8344	0.4284	0.0377	0.084*
H222	0.9156	0.5109	0.0011	0.084*
H223	0.9337	0.4904	0.1045	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S17	0.0406 (3)	0.0580 (4)	0.0483 (4)	0.0010 (3)	0.0158 (3)	−0.0040 (3)
S21	0.0571 (4)	0.0614 (4)	0.0505 (4)	−0.0013 (3)	0.0341 (3)	−0.0052 (3)
N1	0.0458 (11)	0.0510 (10)	0.0343 (10)	−0.0001 (9)	0.0135 (8)	−0.0036 (8)
N2	0.0461 (11)	0.0460 (10)	0.0351 (10)	0.0023 (8)	0.0157 (8)	−0.0016 (8)
N4	0.0431 (10)	0.0387 (9)	0.0315 (9)	0.0004 (8)	0.0151 (8)	0.0010 (7)
N8	0.0475 (11)	0.0490 (10)	0.0386 (10)	−0.0007 (9)	0.0224 (9)	−0.0009 (8)
N9	0.0470 (11)	0.0506 (10)	0.0401 (10)	0.0022 (9)	0.0232 (9)	−0.0007 (8)
N11	0.0533 (12)	0.0532 (11)	0.0548 (12)	0.0129 (10)	0.0196 (10)	0.0027 (10)
N12	0.0525 (12)	0.0544 (11)	0.0522 (12)	0.0094 (9)	0.0237 (10)	−0.0023 (9)
N14	0.0382 (10)	0.0453 (10)	0.0372 (10)	−0.0016 (8)	0.0165 (8)	−0.0044 (8)
C3	0.0428 (12)	0.0319 (10)	0.0381 (12)	0.0010 (9)	0.0172 (10)	0.0033 (8)
C5	0.0435 (12)	0.0299 (9)	0.0340 (11)	−0.0010 (9)	0.0169 (9)	0.0039 (8)
C6	0.0389 (12)	0.0422 (11)	0.0357 (11)	−0.0008 (9)	0.0139 (9)	−0.0008 (9)
C7	0.0493 (13)	0.0349 (10)	0.0320 (11)	0.0016 (9)	0.0188 (9)	0.0052 (8)
C10	0.0391 (12)	0.0493 (12)	0.0337 (11)	0.0012 (9)	0.0143 (9)	−0.0020 (9)
C13	0.0375 (12)	0.0494 (12)	0.0392 (12)	−0.0022 (10)	0.0161 (9)	−0.0091 (9)
C15	0.0343 (11)	0.0458 (11)	0.0323 (11)	−0.0018 (9)	0.0105 (9)	−0.0030 (9)
C16	0.0470 (14)	0.0528 (13)	0.0440 (13)	0.0081 (10)	0.0154 (11)	0.0057 (10)
C18	0.0534 (15)	0.0535 (13)	0.0598 (16)	0.0080 (11)	0.0313 (13)	0.0023 (12)
C19	0.0565 (15)	0.0510 (13)	0.0373 (12)	−0.0026 (11)	0.0198 (11)	−0.0064 (10)
C20	0.0782 (19)	0.0466 (13)	0.0662 (17)	0.0049 (13)	0.0459 (15)	−0.0011 (12)
C22	0.0527 (15)	0.0635 (15)	0.0593 (16)	0.0019 (12)	0.0280 (13)	0.0089 (12)

Geometric parameters (Å, º) top

S17—C3	1.745 (2)	C6—H61	0.9300
S17—C18	1.798 (2)	C7—C19	1.488 (3)
S21—C13	1.751 (2)	C10—C15	1.481 (3)
S21—C22	1.794 (3)	C10—C20	1.487 (3)
N1—C6	1.313 (3)	C15—C16	1.400 (3)
N1—N2	1.352 (3)	C16—H161	0.9300
N2—C3	1.324 (3)	C18—H181	0.9600
N4—C5	1.311 (3)	C18—H182	0.9600
N4—C3	1.352 (3)	C18—H183	0.9600
N8—C7	1.283 (3)	C19—H191	0.9600
N8—N9	1.370 (2)	C19—H192	0.9600
N9—C10	1.279 (3)	C19—H193	0.9600
N11—C16	1.315 (3)	C20—H201	0.9600
N11—N12	1.339 (3)	C20—H202	0.9600
N12—C13	1.337 (3)	C20—H203	0.9600
N14—C15	1.321 (3)	C22—H221	0.9600
N14—C13	1.337 (3)	C22—H222	0.9600
C5—C6	1.412 (3)	C22—H223	0.9600
C5—C7	1.486 (3)

C3—S17—C18	102.76 (12)	N14—C15—C10	117.49 (19)
C13—S21—C22	100.93 (11)	C16—C15—C10	122.7 (2)
C6—N1—N2	118.93 (19)	N11—C16—C15	122.1 (2)
C3—N2—N1	117.08 (18)	N11—C16—H161	119.0
C5—N4—C3	115.11 (18)	C15—C16—H161	119.0
C7—N8—N9	117.19 (19)	S17—C18—H181	109.5
C10—N9—N8	118.97 (18)	S17—C18—H182	109.5
C16—N11—N12	118.7 (2)	H181—C18—H182	109.5
C13—N12—N11	117.58 (19)	S17—C18—H183	109.5
C15—N14—C13	115.32 (19)	H181—C18—H183	109.5
N2—C3—N4	127.1 (2)	H182—C18—H183	109.5
N2—C3—S17	119.62 (17)	C7—C19—H191	109.5
N4—C3—S17	113.23 (17)	C7—C19—H192	109.5
N4—C5—C6	119.94 (19)	H191—C19—H192	109.5
N4—C5—C7	118.52 (19)	C7—C19—H193	109.5
C6—C5—C7	121.5 (2)	H191—C19—H193	109.5
N1—C6—C5	121.8 (2)	H192—C19—H193	109.5
N1—C6—H61	119.1	C10—C20—H201	109.5
C5—C6—H61	119.1	C10—C20—H202	109.5
N8—C7—C19	125.6 (2)	H201—C20—H202	109.5
N8—C7—C5	114.34 (19)	C10—C20—H203	109.5
C19—C7—C5	120.0 (2)	H201—C20—H203	109.5
N9—C10—C15	114.78 (19)	H202—C20—H203	109.5
N9—C10—C20	125.9 (2)	S21—C22—H221	109.5
C15—C10—C20	119.33 (19)	S21—C22—H222	109.5
N12—C13—N14	126.5 (2)	H221—C22—H222	109.5
N12—C13—S21	113.86 (16)	S21—C22—H223	109.5
N14—C13—S21	119.58 (17)	H221—C22—H223	109.5
N14—C15—C16	119.80 (19)	H222—C22—H223	109.5

C6—N1—N2—C3	1.1 (3)	C6—C5—C7—C19	163.73 (19)
C7—N8—N9—C10	114.8 (2)	N8—N9—C10—C15	173.76 (19)
C16—N11—N12—C13	0.3 (3)	N8—N9—C10—C20	−6.5 (4)
N1—N2—C3—N4	0.1 (3)	N11—N12—C13—N14	−2.1 (4)
N1—N2—C3—S17	178.80 (15)	N11—N12—C13—S21	179.33 (17)
C5—N4—C3—N2	−1.6 (3)	C15—N14—C13—N12	2.1 (3)
C5—N4—C3—S17	179.68 (14)	C15—N14—C13—S21	−179.36 (16)
C18—S17—C3—N2	0.15 (19)	C22—S21—C13—N12	−174.30 (19)
C18—S17—C3—N4	179.03 (15)	C22—S21—C13—N14	7.0 (2)
C3—N4—C5—C6	1.8 (3)	C13—N14—C15—C16	−0.5 (3)
C3—N4—C5—C7	179.32 (16)	C13—N14—C15—C10	179.41 (19)
N2—N1—C6—C5	−0.8 (3)	N9—C10—C15—N14	164.3 (2)
N4—C5—C6—N1	−0.7 (3)	C20—C10—C15—N14	−15.4 (3)
C7—C5—C6—N1	−178.20 (18)	N9—C10—C15—C16	−15.8 (3)
N9—N8—C7—C19	−7.1 (3)	C20—C10—C15—C16	164.4 (2)
N9—N8—C7—C5	171.86 (17)	N12—N11—C16—C15	1.2 (4)
N4—C5—C7—N8	167.24 (18)	N14—C15—C16—N11	−1.1 (4)
C6—C5—C7—N8	−15.3 (3)	C10—C15—C16—N11	179.0 (2)
N4—C5—C7—C19	−13.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H193···N4	0.96	2.48	2.875 (3)	104
C20—H202···N8	0.96	2.46	2.816 (3)	101

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₈S₂
M_r	334.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.4962 (4), 7.0814 (2), 15.6619 (5)
β (°)	107.465 (2)
V (Å³)	1533.63 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.24
Crystal size (mm)	0.32 × 0.22 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.474, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	5750, 2635, 2200
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.117, 1.03
No. of reflections	2635
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H193···N4	0.96	2.48	2.875 (3)	104
C20—H202···N8	0.96	2.46	2.816 (3)	101

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Volume 65| Part 8| August 2009| Page o1772

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