Dibromido(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)cobalt(II) acetonitrile monosolvate

Shirvan, S.A.; Aghajeri, M.; Haydari Dezfuli, S.; Khazali, F.; Borsalani, A.

doi:10.1107/S160053681204367X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1407

doi:10.1107/S160053681204367X

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Dibromido(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)cobalt(II) acetonitrile monosolvate

Sadif A. Shirvan,^a ^* Manouchehr Aghajeri,^a Sara Haydari Dezfuli,^a Fereydoon Khazali ^a and Ali Borsalani ^b

^aDepartment of Chemistry, Omidieh Branch, Islamic Azad University, Omidieh, Iran, and ^bDepartment of Petroleum Engineering, Omidieh Branch, Islamic Azad University, Omidieh, Iran
^*Correspondence e-mail: sadifchemist@hotmail.com

(Received 8 October 2012; accepted 22 October 2012; online 27 October 2012)

In the title compound, [CoBr₂(C₁₄H₁₂N₂)]·CH₃CN, the Co^II atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a chelating 2,9-dimethyl-1,10-phenanthroline ligand and two terminal Br atoms. In the crystal, π–π contacts between the pyridine and benzene rings [centroid–centroid distances = 3.828 (5), 3.782 (5), 3.880 (5) and 3.646 (5) Å] stabilize the structure.

Related literature

For related structures, see: Akbarzadeh Torbati et al. (2010 ); Alizadeh et al. (2009 ); Ding et al. (2006 ); Fanizzi et al. (1991 ); Lemoine et al. (2003 ); Robinson & Sinn (1975 ).

Experimental

Crystal data

[CoBr₂(C₁₄H₁₂N₂)]·C₂H₃N
M_r = 468.04
Monoclinic, P 2₁ /n
a = 7.6380 (5) Å
b = 12.7943 (6) Å
c = 17.9545 (11) Å
β = 101.128 (5)°
V = 1721.58 (18) Å³
Z = 4
Mo Kα radiation
μ = 5.64 mm⁻¹
T = 120 K
0.35 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.259, T_max = 0.459
8417 measured reflections
3366 independent reflections
2345 reflections with I > 2σ(I)
R_int = 0.101

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.194
S = 1.02
3366 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 1.11 e Å⁻³
Δρ_min = −1.03 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N1	2.051 (8)
Co1—N2	2.036 (8)
Co1—Br1	2.3592 (14)
Co1—Br2	2.3682 (14)

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: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204367X/hy2596sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204367X/hy2596Isup2.hkl

checkCIF report

Comment top

2,9-Dimethyl-1,10-phenanthroline (dmphen) is a good bidentate ligand, and numerous complexes with dmphen have been prepared, such as that of mercury (Alizadeh et al., 2009), copper (Lemoine et al., 2003), nickel (Ding et al., 2006), gold (Robinson & Sinn, 1975), platinum (Fanizzi et al., 1991) and cobalt (Akbarzadeh Torbati et al., 2010). Here, we report the synthesis and structure of the title compound.

In the title compound (Fig. 1), the Co^II atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a chelating dmphen ligand and two terminal Br atoms. The Co—Br and Co—N bond lengths (Table 1) and angles are normal. In the crystal, π–π contacts between the pyridine and benzene rings (Fig. 2), Cg3···Cg3ⁱ, Cg3···Cg4ⁱ, Cg3···Cg4ⁱⁱ and Cg4···Cg4ⁱⁱ [symmetry codes: (i) -x, 1-y, 1-z; (ii) 1-x, 1-y, 1-z, Cg3 and Cg4 are the centroids of the N2, C8–C11, C13 ring and C5–C8, C13, C14 ring, respectively], with centroid–centroid distances of 3.828 (5), 3.782 (5), 3.880 (5) and 3.646 (5) Å, stabilize the structure.

Related literature top

For related structures, see: Akbarzadeh Torbati et al. (2010); Alizadeh et al. (2009); Ding et al. (2006); Fanizzi et al. (1991); Lemoine et al. (2003); Robinson & Sinn (1975).

Experimental top

For the preparation of the title compound, a solution of 2,9-dimethyl-1,10-phenanthroline (0.28 g, 1.33 mmol) in methanol (20 ml) was added to a solution of CoBr₂ (0.29 g, 1.33 mmol) in acetonitrile (15 ml) and the resulting blue solution was stirred for 15 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, blue block crystals of the title compound were isolated (yield: 0.46 g, 73.9%).

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: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing diagram for the title compound.

Dibromido(2,9-dimethyl-1,10-phenanthroline-κ²N,N')cobalt(II) acetonitrile monosolvate top

Crystal data top

[CoBr₂(C₁₄H₁₂N₂)]·C₂H₃N	F(000) = 916
M_r = 468.04	D_x = 1.806 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8417 reflections
a = 7.6380 (5) Å	θ = 2.0–26.0°
b = 12.7943 (6) Å	µ = 5.64 mm⁻¹
c = 17.9545 (11) Å	T = 120 K
β = 101.128 (5)°	Block, blue
V = 1721.58 (18) Å³	0.35 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3366 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.101
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.259, T_max = 0.459	k = −15→13
8417 measured reflections	l = −22→20

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.194	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1187P)²] where P = (F_o² + 2F_c²)/3
3366 reflections	(Δ/σ)_max = 0.003
200 parameters	Δρ_max = 1.11 e Å⁻³
0 restraints	Δρ_min = −1.03 e Å⁻³

Crystal data top

[CoBr₂(C₁₄H₁₂N₂)]·C₂H₃N	V = 1721.58 (18) Å³
M_r = 468.04	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6380 (5) Å	µ = 5.64 mm⁻¹
b = 12.7943 (6) Å	T = 120 K
c = 17.9545 (11) Å	0.35 × 0.20 × 0.15 mm
β = 101.128 (5)°

Data collection top

Bruker APEXII CCD diffractometer	3366 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2345 reflections with I > 2σ(I)
T_min = 0.259, T_max = 0.459	R_int = 0.101
8417 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.194	H-atom parameters constrained
S = 1.02	Δρ_max = 1.11 e Å⁻³
3366 reflections	Δρ_min = −1.03 e Å⁻³
200 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
Co1	0.15502 (14)	0.35537 (10)	0.33642 (7)	0.0162 (3)
Br1	0.31107 (12)	0.37421 (8)	0.23591 (6)	0.0249 (3)
Br2	−0.12001 (11)	0.26909 (8)	0.29292 (6)	0.0233 (3)
C1	0.3312 (15)	0.1227 (8)	0.3918 (6)	0.032 (2)
H1A	0.3906	0.1476	0.3528	0.038*
H1B	0.2067	0.1129	0.3711	0.038*
H1C	0.3828	0.0574	0.4112	0.038*
C2	0.3520 (11)	0.2011 (8)	0.4548 (5)	0.020 (2)
C3	0.4380 (12)	0.1773 (8)	0.5287 (6)	0.024 (2)
H3	0.4825	0.1103	0.5397	0.029*
C4	0.4587 (10)	0.2517 (8)	0.5861 (5)	0.022 (2)
H4	0.5151	0.2350	0.6353	0.026*
C5	0.3920 (10)	0.3531 (8)	0.5678 (5)	0.0176 (19)
C6	0.4112 (11)	0.4362 (8)	0.6219 (6)	0.022 (2)
H6	0.4712	0.4237	0.6712	0.026*
C7	0.3452 (11)	0.5316 (8)	0.6035 (5)	0.022 (2)
H7	0.3570	0.5835	0.6404	0.026*
C8	0.2557 (10)	0.5549 (7)	0.5268 (5)	0.0178 (19)
C9	0.1829 (12)	0.6513 (8)	0.5024 (7)	0.026 (2)
H9	0.1894	0.7065	0.5365	0.031*
C10	0.1008 (12)	0.6654 (8)	0.4275 (7)	0.028 (2)
H10	0.0564	0.7308	0.4107	0.033*
C11	0.0845 (10)	0.5820 (7)	0.3772 (5)	0.0166 (18)
C12	−0.0028 (13)	0.5960 (8)	0.2951 (6)	0.027 (2)
H12A	−0.1007	0.5481	0.2824	0.033*
H12B	0.0828	0.5825	0.2635	0.033*
H12C	−0.0460	0.6664	0.2870	0.033*
C13	0.2355 (10)	0.4741 (7)	0.4725 (5)	0.0165 (19)
C14	0.3071 (10)	0.3727 (7)	0.4935 (6)	0.0182 (19)
C15	0.1720 (12)	0.9623 (8)	0.5702 (6)	0.027 (2)
C16	0.1350 (16)	1.0197 (10)	0.6364 (7)	0.039 (3)
H16A	0.2341	1.0645	0.6560	0.059*
H16B	0.1176	0.9710	0.6750	0.059*
H16C	0.0293	1.0612	0.6216	0.059*
N1	0.2885 (9)	0.2967 (6)	0.4379 (4)	0.0182 (16)
N2	0.1506 (8)	0.4887 (6)	0.3979 (4)	0.0138 (15)
N3	0.2013 (13)	0.9203 (8)	0.5206 (7)	0.043 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0134 (5)	0.0219 (7)	0.0121 (6)	−0.0001 (5)	−0.0010 (4)	−0.0009 (5)
Br1	0.0201 (4)	0.0384 (6)	0.0167 (5)	−0.0082 (4)	0.0050 (4)	−0.0041 (4)
Br2	0.0160 (4)	0.0306 (6)	0.0222 (5)	−0.0061 (4)	0.0014 (3)	−0.0057 (4)
C1	0.042 (6)	0.025 (6)	0.027 (6)	0.011 (5)	0.005 (5)	0.000 (5)
C2	0.016 (4)	0.028 (5)	0.017 (5)	0.007 (4)	0.002 (3)	0.002 (4)
C3	0.022 (4)	0.018 (5)	0.032 (6)	0.005 (4)	0.008 (4)	0.006 (4)
C4	0.011 (4)	0.041 (6)	0.011 (5)	0.006 (4)	−0.004 (3)	0.008 (4)
C5	0.006 (3)	0.032 (5)	0.015 (5)	−0.001 (3)	0.003 (3)	0.000 (4)
C6	0.013 (4)	0.037 (6)	0.015 (5)	−0.007 (4)	0.004 (3)	−0.002 (4)
C7	0.019 (4)	0.033 (6)	0.012 (5)	−0.005 (4)	0.002 (4)	−0.002 (4)
C8	0.011 (4)	0.026 (5)	0.015 (5)	−0.006 (3)	−0.001 (3)	−0.006 (4)
C9	0.016 (4)	0.022 (5)	0.041 (7)	−0.002 (4)	0.013 (4)	0.000 (5)
C10	0.018 (4)	0.027 (6)	0.040 (7)	0.003 (4)	0.010 (4)	0.003 (5)
C11	0.009 (4)	0.023 (5)	0.019 (5)	0.000 (3)	0.007 (3)	0.002 (4)
C12	0.025 (5)	0.024 (5)	0.034 (6)	0.000 (4)	0.006 (4)	0.008 (5)
C13	0.007 (4)	0.027 (5)	0.015 (5)	−0.005 (3)	0.003 (3)	0.002 (4)
C14	0.008 (4)	0.024 (5)	0.023 (5)	−0.004 (3)	0.002 (3)	−0.005 (4)
C15	0.023 (4)	0.030 (6)	0.027 (6)	0.005 (4)	0.002 (4)	0.005 (5)
C16	0.045 (6)	0.041 (7)	0.026 (6)	−0.007 (5)	−0.005 (5)	−0.003 (5)
N1	0.008 (3)	0.027 (4)	0.020 (4)	0.007 (3)	0.004 (3)	−0.001 (3)
N2	0.006 (3)	0.025 (4)	0.009 (4)	−0.003 (3)	−0.003 (3)	−0.001 (3)
N3	0.043 (5)	0.042 (6)	0.050 (7)	0.019 (5)	0.018 (5)	0.001 (5)

Geometric parameters (Å, º) top

Co1—N1	2.051 (8)	C8—C9	1.390 (14)
Co1—N2	2.036 (8)	C8—C13	1.409 (13)
Co1—Br1	2.3592 (14)	C9—C10	1.382 (16)
Co1—Br2	2.3682 (14)	C9—H9	0.9300
C1—C2	1.497 (14)	C10—C11	1.387 (14)
C1—H1A	0.9600	C10—H10	0.9300
C1—H1B	0.9600	C11—N2	1.321 (12)
C1—H1C	0.9600	C11—C12	1.507 (14)
C2—N1	1.329 (12)	C12—H12A	0.9600
C2—C3	1.395 (14)	C12—H12B	0.9600
C3—C4	1.389 (14)	C12—H12C	0.9600
C3—H3	0.9300	C13—N2	1.383 (11)
C4—C5	1.409 (14)	C13—C14	1.429 (13)
C4—H4	0.9300	C14—N1	1.382 (12)
C5—C14	1.389 (13)	C15—N3	1.099 (15)
C5—C6	1.428 (14)	C15—C16	1.471 (16)
C6—C7	1.337 (14)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—C8	1.444 (13)	C16—H16C	0.9600
C7—H7	0.9300

N2—Co1—N1	83.3 (3)	C10—C9—H9	119.9
N2—Co1—Br1	113.1 (2)	C8—C9—H9	119.9
N1—Co1—Br1	118.62 (19)	C9—C10—C11	119.9 (9)
N2—Co1—Br2	117.58 (18)	C9—C10—H10	120.0
N1—Co1—Br2	112.3 (2)	C11—C10—H10	120.0
Br1—Co1—Br2	110.02 (6)	N2—C11—C10	122.1 (9)
C2—C1—H1A	109.5	N2—C11—C12	117.1 (8)
C2—C1—H1B	109.5	C10—C11—C12	120.8 (9)
H1A—C1—H1B	109.5	C11—C12—H12A	109.5
C2—C1—H1C	109.5	C11—C12—H12B	109.5
H1A—C1—H1C	109.5	H12A—C12—H12B	109.5
H1B—C1—H1C	109.5	C11—C12—H12C	109.5
N1—C2—C3	120.1 (9)	H12A—C12—H12C	109.5
N1—C2—C1	117.5 (8)	H12B—C12—H12C	109.5
C3—C2—C1	122.3 (9)	N2—C13—C8	122.6 (8)
C4—C3—C2	121.4 (9)	N2—C13—C14	117.6 (8)
C4—C3—H3	119.3	C8—C13—C14	119.8 (8)
C2—C3—H3	119.3	N1—C14—C5	122.0 (8)
C3—C4—C5	118.2 (9)	N1—C14—C13	117.8 (8)
C3—C4—H4	120.9	C5—C14—C13	120.1 (8)
C5—C4—H4	120.9	N3—C15—C16	179.1 (13)
C14—C5—C4	118.1 (9)	C15—C16—H16A	109.5
C14—C5—C6	119.0 (9)	C15—C16—H16B	109.5
C4—C5—C6	122.9 (9)	H16A—C16—H16B	109.5
C7—C6—C5	121.9 (9)	C15—C16—H16C	109.5
C7—C6—H6	119.1	H16A—C16—H16C	109.5
C5—C6—H6	119.1	H16B—C16—H16C	109.5
C6—C7—C8	120.7 (9)	C2—N1—C14	120.0 (8)
C6—C7—H7	119.7	C2—N1—Co1	129.6 (7)
C8—C7—H7	119.7	C14—N1—Co1	110.4 (6)
C9—C8—C13	116.7 (9)	C11—N2—C13	118.5 (8)
C9—C8—C7	124.8 (9)	C11—N2—Co1	130.6 (6)
C13—C8—C7	118.5 (9)	C13—N2—Co1	110.9 (6)
C10—C9—C8	120.1 (10)

N1—C2—C3—C4	0.4 (13)	C1—C2—N1—C14	−178.8 (8)
C1—C2—C3—C4	178.9 (9)	C3—C2—N1—Co1	−179.3 (6)
C2—C3—C4—C5	−0.7 (13)	C1—C2—N1—Co1	2.1 (12)
C3—C4—C5—C14	0.8 (11)	C5—C14—N1—C2	0.4 (12)
C3—C4—C5—C6	−177.9 (8)	C13—C14—N1—C2	−179.6 (7)
C14—C5—C6—C7	1.9 (12)	C5—C14—N1—Co1	179.6 (6)
C4—C5—C6—C7	−179.3 (8)	C13—C14—N1—Co1	−0.4 (8)
C5—C6—C7—C8	−1.8 (12)	N2—Co1—N1—C2	179.2 (7)
C6—C7—C8—C9	179.9 (8)	Br1—Co1—N1—C2	−68.1 (8)
C6—C7—C8—C13	1.6 (12)	Br2—Co1—N1—C2	62.1 (7)
C13—C8—C9—C10	−2.0 (12)	N2—Co1—N1—C14	0.0 (5)
C7—C8—C9—C10	179.6 (8)	Br1—Co1—N1—C14	112.7 (5)
C8—C9—C10—C11	2.6 (13)	Br2—Co1—N1—C14	−117.1 (5)
C9—C10—C11—N2	−2.2 (13)	C10—C11—N2—C13	1.2 (11)
C9—C10—C11—C12	−179.3 (8)	C12—C11—N2—C13	178.4 (7)
C9—C8—C13—N2	1.1 (11)	C10—C11—N2—Co1	−177.4 (6)
C7—C8—C13—N2	179.5 (7)	C12—C11—N2—Co1	−0.2 (10)
C9—C8—C13—C14	180.0 (7)	C8—C13—N2—C11	−0.7 (11)
C7—C8—C13—C14	−1.6 (11)	C14—C13—N2—C11	−179.6 (7)
C4—C5—C14—N1	−0.7 (11)	C8—C13—N2—Co1	178.2 (6)
C6—C5—C14—N1	178.1 (7)	C14—C13—N2—Co1	−0.7 (8)
C4—C5—C14—C13	179.3 (7)	N1—Co1—N2—C11	179.1 (7)
C6—C5—C14—C13	−1.9 (11)	Br1—Co1—N2—C11	60.8 (7)
N2—C13—C14—N1	0.7 (10)	Br2—Co1—N2—C11	−69.2 (7)
C8—C13—C14—N1	−178.2 (7)	N1—Co1—N2—C13	0.4 (5)
N2—C13—C14—C5	−179.3 (7)	Br1—Co1—N2—C13	−117.9 (5)
C8—C13—C14—C5	1.8 (11)	Br2—Co1—N2—C13	112.1 (5)
C3—C2—N1—C14	−0.2 (12)

Experimental details

Crystal data
Chemical formula	[CoBr₂(C₁₄H₁₂N₂)]·C₂H₃N
M_r	468.04
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	7.6380 (5), 12.7943 (6), 17.9545 (11)
β (°)	101.128 (5)
V (Å³)	1721.58 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.64
Crystal size (mm)	0.35 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.259, 0.459
No. of measured, independent and observed [I > 2σ(I)] reflections	8417, 3366, 2345
R_int	0.101
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.194, 1.02
No. of reflections	3366
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.11, −1.03

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—N1	2.051 (8)	Co1—Br1	2.3592 (14)
Co1—N2	2.036 (8)	Co1—Br2	2.3682 (14)

Acknowledgements

We are grateful to the Omidieh Branch, Islamic Azad University, for financial support.

References

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