5-(1H-Imidazol-1-ylsulfon­yl)-N,N-dimethyl­naphthalen-1-amine

Teng, L.; Zhang, Y.; Zhang, S.; Qu, Y.; Xia, X.

doi:10.1107/S160053680804066X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o55

doi:10.1107/S160053680804066X

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5-(1H-Imidazol-1-ylsulfonyl)-N,N-dimethylnaphthalen-1-amine

Lei Teng,^a Yong Zhang,^a ^* Shi-lei Zhang,^a Yuan Qu ^a and Xian-you Xia ^a

^aSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: zy0340907@yahoo.com.cn

(Received 26 November 2008; accepted 3 December 2008; online 10 December 2008)

In the title molecule, C₁₅H₁₅N₃O₂S, the dihedral angle between the naphthalene ring system and the imidazole ring is 86.1 (2)°. In the crystal structure, weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds, as well as weak C—H⋯π interactions, connect molecules, forming a two-dimensional network.

Related literature

For background information, see: Corradini et al. (1997 ); Kavallieratos et al. (2005 ); Koike et al. (1996 ). For the synthesis, see: Hilderbrand et al. (2004 ).

Experimental

Crystal data

C₁₅H₁₅N₃O₂S
M_r = 301.36
Orthorhombic, P b c a
a = 16.3707 (16) Å
b = 7.7928 (7) Å
c = 22.088 (2) Å
V = 2817.8 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 150 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.944, T_max = 0.977
9800 measured reflections
2577 independent reflections
2196 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.110
S = 1.07
2577 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2	0.95	2.42	3.057 (2)	125
C15—H15⋯N3ⁱ	0.95	2.45	3.395 (3)	173
C14—H14⋯O2ⁱⁱ	0.95	2.45	3.358 (3)	161
C13—H13⋯N1ⁱⁱⁱ	0.95	2.57	3.506 (2)	169
C10—H10⋯Cg^iv	0.95	2.82	3.302 (2)	113
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) x, y-1, z; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ . Cg is the centroid of the C3–C7/C12 ring.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804066X/lh2737sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680804066X/lh2737Isup2.hkl

checkCIF report

Comment top

Dansyl chloride is widely used as a fluorescent label in immunofluorescence methods and in yielding fluorescent N-terminal amino acids and peptide derivatives. Some dansyl chloride derivatives are also used as fluorescent probes, which can detect trace metal ions such as Pb²⁺, Cu²⁺, Zn²⁺ (Koike et al., 1996; Corradini et al., 1997; Kavallieratos et al., 2005). We are interested in preparing fluorescent drug or ligand analogs that are expected to bind to hydrophobic sites in proteins or membranes. With this mind, the title compound, (I), was prepared and we report the crystal stucture herein.

In the molecular structure (Fig. 1), the dihedral angle between the naphthalene ring and the imidazole ring is 86.1 (2)°. All bond lengths and bond angles are as expected. In the crystal structure (Fig.2), the molecules are linked by C–H···O and C—H···N hydrogen bonds (Table 1) and C—H···π interactions into a two-dimension network.

Related literature top

For background information, see: Corradini et al. (1997); Kavallieratos et al. (2005); Koike et al. (1996). For the synthesis, see: Hilderbrand et al. (2004). Cg is the centroid of the C3–C7/C12 ring.

Experimental top

Compound (I) was synthesized according to a literature procedure (Hilderbrand et al., 2004). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution of (I) at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of (I) showing weak hydrogen bonds as dashed lines.

5-(1H-Imidazol-1-ylsulfonyl)-N,N-dimethylnaphthalen-1-amine top

Crystal data top

C₁₅H₁₅N₃O₂S	F(000) = 1264
M_r = 301.36	D_x = 1.421 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3852 reflections
a = 16.3707 (16) Å	θ = 2.2–28.2°
b = 7.7928 (7) Å	µ = 0.24 mm⁻¹
c = 22.088 (2) Å	T = 150 K
V = 2817.8 (5) Å³	Block, red
Z = 8	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	2577 independent reflections
Radiation source: fine-focus sealed tube	2196 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→19
T_min = 0.944, T_max = 0.977	k = −7→9
9800 measured reflections	l = −26→25

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: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0583P)² + 0.6727P] where P = (F_o² + 2F_c²)/3
2577 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₅H₁₅N₃O₂S	V = 2817.8 (5) Å³
M_r = 301.36	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.3707 (16) Å	µ = 0.24 mm⁻¹
b = 7.7928 (7) Å	T = 150 K
c = 22.088 (2) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	2577 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2196 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.977	R_int = 0.058
9800 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.07	Δρ_max = 0.50 e Å⁻³
2577 reflections	Δρ_min = −0.31 e Å⁻³
192 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
C1	0.11008 (13)	−0.0608 (3)	0.10523 (10)	0.0274 (5)
H1A	0.1612	−0.1147	0.0922	0.041*
H1B	0.0721	−0.0558	0.0710	0.041*
H1C	0.0858	−0.1285	0.1380	0.041*
C2	0.18098 (13)	0.2027 (3)	0.08508 (9)	0.0319 (5)
H2A	0.1877	0.3221	0.0981	0.048*
H2B	0.1574	0.2002	0.0443	0.048*
H2C	0.2343	0.1457	0.0846	0.048*
C3	0.14436 (11)	0.1301 (3)	0.18942 (8)	0.0216 (4)
C4	0.21791 (12)	0.1896 (3)	0.21123 (9)	0.0247 (5)
H4	0.2602	0.2184	0.1836	0.030*
C5	0.23134 (11)	0.2084 (3)	0.27371 (9)	0.0255 (5)
H5	0.2825	0.2507	0.2874	0.031*
C6	0.17273 (11)	0.1673 (3)	0.31536 (9)	0.0234 (4)
H6	0.1840	0.1773	0.3574	0.028*
C7	0.09481 (11)	0.1098 (2)	0.29548 (9)	0.0193 (4)
C8	0.02739 (11)	0.0735 (2)	0.33507 (9)	0.0193 (4)
C9	−0.04868 (11)	0.0311 (3)	0.31351 (9)	0.0214 (4)
H9	−0.0917	0.0063	0.3410	0.026*
C10	−0.06277 (11)	0.0244 (3)	0.25099 (9)	0.0221 (4)
H10	−0.1159	−0.0007	0.2360	0.026*
C11	−0.00036 (11)	0.0539 (2)	0.21174 (9)	0.0207 (4)
H11	−0.0107	0.0476	0.1695	0.025*
C12	0.08007 (11)	0.0938 (2)	0.23193 (9)	0.0201 (4)
C13	0.06482 (12)	−0.2592 (3)	0.42799 (9)	0.0235 (5)
H13	0.0112	−0.2976	0.4187	0.028*
C14	0.13037 (12)	−0.3564 (3)	0.44095 (9)	0.0280 (5)
H14	0.1302	−0.4783	0.4420	0.034*
C15	0.17381 (12)	−0.0973 (3)	0.44626 (9)	0.0238 (5)
H15	0.2077	0.0005	0.4514	0.029*
N1	0.12680 (9)	0.1138 (2)	0.12696 (7)	0.0224 (4)
N2	0.09210 (9)	−0.0906 (2)	0.43108 (7)	0.0189 (4)
N3	0.19833 (10)	−0.2548 (2)	0.45265 (8)	0.0295 (4)
O1	−0.04379 (8)	0.04896 (19)	0.43910 (6)	0.0269 (4)
O2	0.08176 (8)	0.22535 (18)	0.43451 (6)	0.0274 (4)
S1	0.03535 (3)	0.08123 (6)	0.41480 (2)	0.02021 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0290 (10)	0.0248 (13)	0.0283 (11)	0.0020 (9)	0.0010 (9)	−0.0029 (9)
C2	0.0303 (11)	0.0407 (14)	0.0248 (10)	−0.0036 (10)	0.0055 (9)	0.0055 (10)
C3	0.0222 (9)	0.0177 (11)	0.0251 (10)	0.0019 (8)	0.0009 (8)	0.0024 (8)
C4	0.0194 (9)	0.0245 (12)	0.0302 (11)	−0.0013 (8)	0.0048 (8)	0.0025 (9)
C5	0.0178 (9)	0.0250 (12)	0.0337 (11)	−0.0014 (8)	−0.0041 (8)	−0.0010 (9)
C6	0.0226 (9)	0.0224 (12)	0.0251 (10)	−0.0001 (8)	−0.0045 (8)	−0.0002 (8)
C7	0.0199 (9)	0.0163 (11)	0.0218 (10)	0.0023 (8)	−0.0009 (7)	0.0015 (8)
C8	0.0220 (9)	0.0158 (11)	0.0201 (10)	0.0016 (8)	−0.0015 (7)	0.0013 (8)
C9	0.0208 (9)	0.0197 (11)	0.0238 (10)	−0.0010 (8)	0.0026 (8)	0.0008 (8)
C10	0.0181 (9)	0.0211 (11)	0.0270 (11)	−0.0021 (8)	−0.0042 (8)	−0.0001 (9)
C11	0.0227 (10)	0.0205 (12)	0.0190 (9)	0.0003 (8)	−0.0044 (8)	0.0015 (8)
C12	0.0192 (9)	0.0164 (11)	0.0247 (11)	0.0015 (8)	−0.0011 (8)	0.0021 (8)
C13	0.0246 (10)	0.0234 (12)	0.0226 (10)	−0.0060 (9)	−0.0018 (8)	−0.0014 (8)
C14	0.0337 (11)	0.0187 (12)	0.0316 (11)	−0.0002 (9)	−0.0014 (9)	−0.0017 (9)
C15	0.0200 (9)	0.0247 (12)	0.0266 (11)	−0.0024 (8)	−0.0030 (8)	0.0002 (8)
N1	0.0231 (8)	0.0233 (10)	0.0209 (9)	−0.0022 (7)	0.0025 (7)	0.0018 (7)
N2	0.0207 (8)	0.0179 (9)	0.0182 (8)	0.0004 (6)	−0.0016 (6)	−0.0003 (6)
N3	0.0247 (9)	0.0259 (11)	0.0377 (10)	0.0024 (7)	−0.0056 (7)	0.0012 (8)
O1	0.0232 (7)	0.0357 (9)	0.0216 (7)	0.0041 (6)	0.0028 (5)	−0.0006 (6)
O2	0.0325 (8)	0.0221 (8)	0.0276 (7)	0.0006 (6)	−0.0025 (6)	−0.0041 (6)
S1	0.0221 (3)	0.0203 (3)	0.0183 (3)	0.00270 (19)	−0.00034 (18)	−0.00119 (19)

Geometric parameters (Å, º) top

C1—N1	1.468 (3)	C8—C9	1.374 (3)
C1—H1A	0.9800	C8—S1	1.767 (2)
C1—H1B	0.9800	C9—C10	1.401 (3)
C1—H1C	0.9800	C9—H9	0.9500
C2—N1	1.457 (2)	C10—C11	1.359 (3)
C2—H2A	0.9800	C10—H10	0.9500
C2—H2B	0.9800	C11—C12	1.424 (3)
C2—H2C	0.9800	C11—H11	0.9500
C3—C4	1.377 (3)	C13—C14	1.344 (3)
C3—N1	1.415 (2)	C13—N2	1.389 (3)
C3—C12	1.438 (3)	C13—H13	0.9500
C4—C5	1.405 (3)	C14—N3	1.390 (3)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.367 (3)	C15—N3	1.299 (3)
C5—H5	0.9500	C15—N2	1.380 (2)
C6—C7	1.422 (3)	C15—H15	0.9500
C6—H6	0.9500	N2—S1	1.6692 (16)
C7—C12	1.430 (3)	O1—S1	1.4249 (14)
C7—C8	1.436 (3)	O2—S1	1.4241 (14)

N1—C1—H1A	109.5	C10—C9—H9	120.0
N1—C1—H1B	109.5	C11—C10—C9	119.90 (17)
H1A—C1—H1B	109.5	C11—C10—H10	120.0
N1—C1—H1C	109.5	C9—C10—H10	120.0
H1A—C1—H1C	109.5	C10—C11—C12	122.14 (18)
H1B—C1—H1C	109.5	C10—C11—H11	118.9
N1—C2—H2A	109.5	C12—C11—H11	118.9
N1—C2—H2B	109.5	C11—C12—C7	118.84 (17)
H2A—C2—H2B	109.5	C11—C12—C3	120.99 (17)
N1—C2—H2C	109.5	C7—C12—C3	120.00 (16)
H2A—C2—H2C	109.5	C14—C13—N2	105.42 (17)
H2B—C2—H2C	109.5	C14—C13—H13	127.3
C4—C3—N1	123.28 (17)	N2—C13—H13	127.3
C4—C3—C12	118.54 (17)	C13—C14—N3	110.95 (19)
N1—C3—C12	118.04 (16)	C13—C14—H14	124.5
C3—C4—C5	121.01 (18)	N3—C14—H14	124.5
C3—C4—H4	119.5	N3—C15—N2	111.22 (17)
C5—C4—H4	119.5	N3—C15—H15	124.4
C6—C5—C4	121.79 (18)	N2—C15—H15	124.4
C6—C5—H5	119.1	C3—N1—C2	116.91 (16)
C4—C5—H5	119.1	C3—N1—C1	116.09 (16)
C5—C6—C7	119.71 (18)	C2—N1—C1	110.30 (16)
C5—C6—H6	120.1	C15—N2—C13	106.73 (16)
C7—C6—H6	120.1	C15—N2—S1	128.48 (14)
C6—C7—C12	118.84 (17)	C13—N2—S1	124.69 (13)
C6—C7—C8	124.31 (17)	C15—N3—C14	105.70 (17)
C12—C7—C8	116.79 (16)	O2—S1—O1	120.60 (9)
C9—C8—C7	122.21 (18)	O2—S1—N2	105.66 (8)
C9—C8—S1	114.88 (14)	O1—S1—N2	106.46 (9)
C7—C8—S1	122.91 (14)	O2—S1—C8	111.78 (9)
C8—C9—C10	119.99 (17)	O1—S1—C8	107.60 (8)
C8—C9—H9	120.0	N2—S1—C8	103.20 (8)

N1—C3—C4—C5	178.02 (18)	N2—C13—C14—N3	0.5 (2)
C12—C3—C4—C5	2.5 (3)	C4—C3—N1—C2	−15.4 (3)
C3—C4—C5—C6	0.5 (3)	C12—C3—N1—C2	160.21 (18)
C4—C5—C6—C7	−2.3 (3)	C4—C3—N1—C1	117.6 (2)
C5—C6—C7—C12	0.9 (3)	C12—C3—N1—C1	−66.8 (2)
C5—C6—C7—C8	−176.03 (19)	N3—C15—N2—C13	0.0 (2)
C6—C7—C8—C9	174.8 (2)	N3—C15—N2—S1	−176.46 (14)
C12—C7—C8—C9	−2.2 (3)	C14—C13—N2—C15	−0.3 (2)
C6—C7—C8—S1	−4.7 (3)	C14—C13—N2—S1	176.33 (14)
C12—C7—C8—S1	178.26 (14)	N2—C15—N3—C14	0.3 (2)
C7—C8—C9—C10	−0.8 (3)	C13—C14—N3—C15	−0.5 (2)
S1—C8—C9—C10	178.69 (15)	C15—N2—S1—O2	−14.58 (19)
C8—C9—C10—C11	2.4 (3)	C13—N2—S1—O2	169.57 (15)
C9—C10—C11—C12	−0.7 (3)	C15—N2—S1—O1	−143.94 (17)
C10—C11—C12—C7	−2.5 (3)	C13—N2—S1—O1	40.22 (18)
C10—C11—C12—C3	−177.88 (19)	C15—N2—S1—C8	102.91 (18)
C6—C7—C12—C11	−173.40 (18)	C13—N2—S1—C8	−72.93 (17)
C8—C7—C12—C11	3.8 (3)	C9—C8—S1—O2	−137.71 (15)
C6—C7—C12—C3	2.1 (3)	C7—C8—S1—O2	41.82 (18)
C8—C7—C12—C3	179.25 (17)	C9—C8—S1—O1	−3.13 (18)
C4—C3—C12—C11	171.62 (19)	C7—C8—S1—O1	176.40 (16)
N1—C3—C12—C11	−4.2 (3)	C9—C8—S1—N2	109.19 (16)
C4—C3—C12—C7	−3.7 (3)	C7—C8—S1—N2	−71.28 (17)
N1—C3—C12—C7	−179.52 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.95	2.42	3.057 (2)	125
C15—H15···N3ⁱ	0.95	2.45	3.395 (3)	173
C14—H14···O2ⁱⁱ	0.95	2.45	3.358 (3)	161
C13—H13···N1ⁱⁱⁱ	0.95	2.57	3.506 (2)	169
C10—H10···Cg^iv	0.95	2.82	3.302 (2)	113

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₃O₂S
M_r	301.36
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	150
a, b, c (Å)	16.3707 (16), 7.7928 (7), 22.088 (2)
V (Å³)	2817.8 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.944, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	9800, 2577, 2196
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 1.07
No. of reflections	2577
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.31

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.95	2.42	3.057 (2)	124.5
C15—H15···N3ⁱ	0.95	2.45	3.395 (3)	173.2
C14—H14···O2ⁱⁱ	0.95	2.45	3.358 (3)	160.5
C13—H13···N1ⁱⁱⁱ	0.95	2.57	3.506 (2)	169.2
C10—H10···Cg^iv	0.95	2.82	3.302 (2)	113

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

References

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Volume 65| Part 1| January 2009| Page o55

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