5-(4-Fluoro-phen-yl)-3-[5-methyl-1-(4-methyl-phen-yl)-1H-1,2,3-triazol-4-yl]-N-phenyl-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

In the title compound, C26H23FN6S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The thio-urea group is close to being coplanar with the pyrazole N atoms [N-N-C-S torsion angle = 176.78 (15)°], which allows for an intra-molecular N-H⋯N hydrogen bond; the connected triazole ring is nearly coplanar with this ring [N-C-C-N = -172.65 (19)°]. There is a significant twist between the pyrazole ring and attached fluoro-benzene ring [N-C-C-C = -18.8 (3)°] and a greater twist between triazole and attached tolyl ring [dihedral angle = 58.25 (14)°]. In the crystal, supra-molecular chains aligned along [40,10] are consolidated by π-π inter-actions between the triazole and phenyl rings [centroid-centroid distance = 3.7053 (13) Å].

Related literature

For the biological activity and synthesis of related compounds, see: Abdel-Wahab, Abdel-Latif et al. (2012 ▶). For a related structure, see: Abdel-Wahab, Mohamed et al. (2012 ▶).

Experimental

Crystal data

C26H23FN6S

M = 470.56

Monoclinic,

a = 6.5449 (5) Å

b = 26.1030 (17) Å

c = 14.3818 (8) Å

β = 100.604 (7)°

V = 2415.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 295 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.802, T max = 1.000

15173 measured reflections

5578 independent reflections

3313 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.162

S = 1.03

5578 reflections

313 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008155/hg5303sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008155/hg5303Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008155/hg5303Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H23FN6S	F(000) = 984
Mr = 470.56	Dx = 1.294 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2937 reflections
a = 6.5449 (5) Å	θ = 2.9–27.5°
b = 26.1030 (17) Å	µ = 0.17 mm−1
c = 14.3818 (8) Å	T = 295 K
β = 100.604 (7)°	Prism, colourless
V = 2415.0 (3) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	5578 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3313 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.040
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −33→33
Tmin = 0.802, Tmax = 1.000	l = −18→18
15173 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0643P)2 + 0.3514P] where P = (Fo2 + 2Fc2)/3
5578 reflections	(Δ/σ)max = 0.001
313 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.28247 (11)	0.59566 (2)	0.26576 (4)	0.0660 (2)
F1	0.4921 (5)	0.53780 (11)	0.71572 (17)	0.1882 (13)
N1	0.2779 (3)	0.69941 (8)	0.25175 (14)	0.0581 (5)
N2	0.5580 (3)	0.66351 (7)	0.34286 (12)	0.0538 (5)
N3	0.6368 (3)	0.71314 (7)	0.35592 (12)	0.0519 (5)
N4	1.1621 (3)	0.75227 (8)	0.45157 (14)	0.0624 (5)
N5	1.2414 (3)	0.79826 (8)	0.45671 (15)	0.0662 (6)
N6	1.0814 (3)	0.83112 (8)	0.42485 (12)	0.0584 (5)
C1	0.0777 (3)	0.71154 (8)	0.20191 (14)	0.0503 (5)
C2	0.0342 (4)	0.76336 (9)	0.18895 (15)	0.0580 (6)
H2	0.1373	0.7873	0.2105	0.070*
C3	−0.1592 (4)	0.77990 (10)	0.14473 (15)	0.0635 (7)
H3A	−0.1860	0.8148	0.1371	0.076*
C4	−0.3132 (4)	0.74477 (11)	0.11172 (15)	0.0655 (7)
H4	−0.4442	0.7557	0.0819	0.079*
C5	−0.2697 (4)	0.69365 (11)	0.12361 (16)	0.0659 (7)
H5	−0.3729	0.6699	0.1012	0.079*
C6	−0.0762 (4)	0.67637 (9)	0.16809 (15)	0.0608 (6)
H6	−0.0500	0.6414	0.1751	0.073*
C7	0.3712 (4)	0.65505 (8)	0.28600 (14)	0.0504 (5)
C8	0.7040 (3)	0.62449 (9)	0.39009 (14)	0.0532 (6)
H8	0.7241	0.5976	0.3451	0.064*
C9	0.9037 (3)	0.65642 (9)	0.41746 (16)	0.0572 (6)
H9A	0.9644	0.6520	0.4837	0.069*
H9B	1.0056	0.6472	0.3792	0.069*
C10	0.8281 (3)	0.70984 (9)	0.39768 (14)	0.0503 (5)
C11	0.6339 (4)	0.60126 (9)	0.47522 (15)	0.0547 (6)
C12	0.4899 (4)	0.62432 (10)	0.51996 (17)	0.0666 (7)
H12	0.4242	0.6543	0.4956	0.080*
C13	0.4429 (5)	0.60252 (14)	0.6021 (2)	0.0936 (10)
H13	0.3470	0.6179	0.6336	0.112*
C14	0.5405 (7)	0.55819 (17)	0.6353 (2)	0.1117 (13)
C15	0.6779 (7)	0.53446 (15)	0.5924 (3)	0.1172 (13)
H15	0.7404	0.5041	0.6164	0.141*
C16	0.7249 (5)	0.55604 (11)	0.5117 (2)	0.0877 (9)
H16	0.8202	0.5398	0.4810	0.105*
C17	0.9534 (3)	0.75537 (9)	0.41700 (14)	0.0520 (5)
C18	0.8996 (3)	0.80599 (9)	0.39990 (14)	0.0530 (5)
C19	0.6961 (4)	0.83117 (10)	0.36692 (18)	0.0669 (7)
H19A	0.7083	0.8672	0.3802	0.100*
H19B	0.5940	0.8165	0.3991	0.100*
H19C	0.6543	0.8261	0.3000	0.100*
C20	1.1213 (4)	0.88469 (10)	0.41824 (18)	0.0636 (6)
C21	1.2087 (4)	0.91154 (11)	0.4967 (2)	0.0790 (8)
H21	1.2441	0.8953	0.5550	0.095*
C22	1.2439 (5)	0.96392 (12)	0.4878 (3)	0.0979 (10)
H22	1.3019	0.9826	0.5413	0.117*
C23	1.1953 (5)	0.98862 (13)	0.4024 (3)	0.1023 (11)
C24	1.1078 (6)	0.95997 (14)	0.3244 (3)	0.1113 (12)
H24	1.0730	0.9758	0.2657	0.134*
C25	1.0717 (5)	0.90862 (12)	0.3320 (2)	0.0926 (10)
H25	1.0134	0.8899	0.2786	0.111*
C26	1.2352 (5)	1.04560 (13)	0.3937 (4)	0.151 (2)
H26A	1.2715	1.0604	0.4556	0.227*
H26B	1.1121	1.0619	0.3599	0.227*
H26C	1.3473	1.0506	0.3599	0.227*
H3	0.355 (5)	0.7242 (10)	0.2690 (19)	0.080 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0670 (5)	0.0540 (4)	0.0691 (4)	0.0000 (3)	−0.0082 (3)	−0.0048 (3)
F1	0.231 (3)	0.219 (3)	0.1311 (18)	−0.018 (2)	0.0773 (19)	0.0845 (19)
N1	0.0465 (12)	0.0515 (12)	0.0686 (12)	−0.0016 (9)	−0.0094 (10)	0.0012 (10)
N2	0.0447 (11)	0.0541 (11)	0.0577 (10)	−0.0005 (9)	−0.0038 (9)	0.0055 (9)
N3	0.0419 (11)	0.0577 (11)	0.0533 (10)	−0.0040 (9)	0.0018 (9)	0.0021 (8)
N4	0.0391 (11)	0.0766 (14)	0.0691 (12)	−0.0062 (10)	0.0038 (9)	0.0110 (10)
N5	0.0392 (11)	0.0766 (14)	0.0799 (13)	−0.0071 (10)	0.0033 (10)	0.0126 (11)
N6	0.0420 (11)	0.0739 (13)	0.0585 (10)	−0.0079 (10)	0.0069 (9)	0.0072 (10)
C1	0.0435 (13)	0.0598 (14)	0.0438 (10)	0.0014 (10)	−0.0018 (9)	0.0020 (10)
C2	0.0570 (15)	0.0587 (14)	0.0543 (12)	0.0013 (11)	−0.0001 (11)	0.0060 (10)
C3	0.0608 (16)	0.0713 (16)	0.0552 (13)	0.0141 (13)	0.0023 (12)	0.0123 (12)
C4	0.0492 (15)	0.0914 (19)	0.0517 (12)	0.0119 (14)	−0.0018 (11)	0.0060 (13)
C5	0.0490 (15)	0.0826 (18)	0.0605 (13)	−0.0044 (13)	−0.0046 (12)	−0.0059 (13)
C6	0.0532 (15)	0.0620 (14)	0.0617 (13)	0.0002 (12)	−0.0042 (11)	−0.0070 (11)
C7	0.0473 (13)	0.0569 (13)	0.0445 (10)	0.0017 (10)	0.0020 (10)	0.0008 (10)
C8	0.0475 (13)	0.0581 (14)	0.0511 (11)	0.0086 (10)	0.0013 (10)	0.0023 (10)
C9	0.0400 (13)	0.0709 (15)	0.0592 (12)	0.0056 (11)	0.0049 (10)	0.0081 (11)
C10	0.0392 (12)	0.0660 (14)	0.0450 (10)	0.0006 (10)	0.0059 (9)	0.0041 (10)
C11	0.0489 (14)	0.0561 (13)	0.0555 (12)	−0.0058 (11)	−0.0001 (11)	0.0023 (10)
C12	0.0601 (16)	0.0752 (17)	0.0637 (14)	−0.0069 (13)	0.0092 (13)	−0.0015 (13)
C13	0.085 (2)	0.122 (3)	0.0793 (19)	−0.018 (2)	0.0293 (17)	−0.0031 (19)
C14	0.124 (3)	0.132 (3)	0.081 (2)	−0.026 (3)	0.023 (2)	0.041 (2)
C15	0.131 (3)	0.108 (3)	0.111 (3)	0.013 (2)	0.020 (3)	0.055 (2)
C16	0.092 (2)	0.082 (2)	0.0896 (19)	0.0178 (17)	0.0177 (17)	0.0252 (17)
C17	0.0385 (12)	0.0715 (15)	0.0453 (10)	−0.0048 (11)	0.0058 (9)	0.0062 (10)
C18	0.0407 (13)	0.0708 (15)	0.0479 (11)	−0.0051 (11)	0.0088 (10)	0.0043 (11)
C19	0.0452 (14)	0.0740 (17)	0.0788 (16)	0.0009 (12)	0.0045 (12)	0.0087 (13)
C20	0.0442 (14)	0.0697 (16)	0.0753 (16)	−0.0098 (12)	0.0070 (12)	0.0136 (13)
C21	0.0627 (18)	0.0807 (19)	0.0870 (18)	−0.0114 (14)	−0.0036 (15)	0.0070 (15)
C22	0.062 (2)	0.079 (2)	0.142 (3)	−0.0133 (16)	−0.009 (2)	−0.003 (2)
C23	0.0480 (17)	0.078 (2)	0.175 (3)	−0.0001 (15)	0.004 (2)	0.039 (2)
C24	0.088 (3)	0.112 (3)	0.129 (3)	−0.015 (2)	0.007 (2)	0.055 (2)
C25	0.096 (2)	0.097 (2)	0.0811 (18)	−0.0215 (18)	0.0057 (17)	0.0258 (17)
C26	0.076 (2)	0.074 (2)	0.291 (6)	−0.0018 (18)	−0.002 (3)	0.058 (3)

S1—C7	1.662 (2)	C10—C17	1.442 (3)
F1—C14	1.363 (4)	C11—C12	1.374 (3)
N1—C7	1.358 (3)	C11—C16	1.381 (3)
N1—C1	1.409 (3)	C12—C13	1.395 (4)
N1—H3	0.83 (3)	C12—H12	0.9300
N2—C7	1.358 (3)	C13—C14	1.365 (5)
N2—N3	1.394 (2)	C13—H13	0.9300
N2—C8	1.474 (3)	C14—C15	1.333 (5)
N3—C10	1.288 (3)	C15—C16	1.375 (4)
N4—N5	1.305 (3)	C15—H15	0.9300
N4—C17	1.367 (3)	C16—H16	0.9300
N5—N6	1.366 (3)	C17—C18	1.378 (3)
N6—C18	1.348 (3)	C18—C19	1.482 (3)
N6—C20	1.429 (3)	C19—H19A	0.9600
C1—C6	1.383 (3)	C19—H19B	0.9600
C1—C2	1.388 (3)	C19—H19C	0.9600
C2—C3	1.377 (3)	C20—C21	1.361 (4)
C2—H2	0.9300	C20—C25	1.373 (4)
C3—C4	1.381 (4)	C21—C22	1.396 (4)
C3—H3A	0.9300	C21—H21	0.9300
C4—C5	1.368 (4)	C22—C23	1.372 (5)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.385 (3)	C23—C24	1.382 (5)
C5—H5	0.9300	C23—C26	1.519 (4)
C6—H6	0.9300	C24—C25	1.369 (4)
C8—C11	1.511 (3)	C24—H24	0.9300
C8—C9	1.539 (3)	C25—H25	0.9300
C8—H8	0.9800	C26—H26A	0.9600
C9—C10	1.489 (3)	C26—H26B	0.9600
C9—H9A	0.9700	C26—H26C	0.9600
C9—H9B	0.9700
C7—N1—C1	133.6 (2)	C11—C12—C13	119.7 (3)
C7—N1—H3	110 (2)	C11—C12—H12	120.2
C1—N1—H3	116 (2)	C13—C12—H12	120.2
C7—N2—N3	120.12 (17)	C14—C13—C12	118.7 (3)
C7—N2—C8	126.89 (18)	C14—C13—H13	120.7
N3—N2—C8	112.83 (17)	C12—C13—H13	120.7
C10—N3—N2	107.71 (17)	C15—C14—F1	119.6 (4)
N5—N4—C17	109.1 (2)	C15—C14—C13	123.0 (3)
N4—N5—N6	106.63 (18)	F1—C14—C13	117.5 (4)
C18—N6—N5	111.6 (2)	C14—C15—C16	118.4 (3)
C18—N6—C20	128.4 (2)	C14—C15—H15	120.8
N5—N6—C20	119.91 (19)	C16—C15—H15	120.8
C6—C1—C2	118.8 (2)	C15—C16—C11	121.5 (3)
C6—C1—N1	125.3 (2)	C15—C16—H16	119.2
C2—C1—N1	115.9 (2)	C11—C16—H16	119.2
C3—C2—C1	121.1 (2)	N4—C17—C18	109.1 (2)
C3—C2—H2	119.5	N4—C17—C10	121.1 (2)
C1—C2—H2	119.5	C18—C17—C10	129.7 (2)
C2—C3—C4	120.1 (2)	N6—C18—C17	103.6 (2)
C2—C3—H3A	120.0	N6—C18—C19	124.5 (2)
C4—C3—H3A	120.0	C17—C18—C19	131.9 (2)
C5—C4—C3	118.9 (2)	C18—C19—H19A	109.5
C5—C4—H4	120.6	C18—C19—H19B	109.5
C3—C4—H4	120.6	H19A—C19—H19B	109.5
C4—C5—C6	121.8 (2)	C18—C19—H19C	109.5
C4—C5—H5	119.1	H19A—C19—H19C	109.5
C6—C5—H5	119.1	H19B—C19—H19C	109.5
C1—C6—C5	119.4 (2)	C21—C20—C25	120.5 (3)
C1—C6—H6	120.3	C21—C20—N6	120.2 (2)
C5—C6—H6	120.3	C25—C20—N6	119.3 (2)
N1—C7—N2	111.98 (19)	C20—C21—C22	118.6 (3)
N1—C7—S1	127.76 (17)	C20—C21—H21	120.7
N2—C7—S1	120.26 (16)	C22—C21—H21	120.7
N2—C8—C11	112.53 (19)	C23—C22—C21	121.8 (3)
N2—C8—C9	101.03 (17)	C23—C22—H22	119.1
C11—C8—C9	112.35 (18)	C21—C22—H22	119.1
N2—C8—H8	110.2	C22—C23—C24	117.8 (3)
C11—C8—H8	110.2	C22—C23—C26	121.3 (4)
C9—C8—H8	110.2	C24—C23—C26	121.0 (4)
C10—C9—C8	102.80 (18)	C25—C24—C23	121.1 (3)
C10—C9—H9A	111.2	C25—C24—H24	119.4
C8—C9—H9A	111.2	C23—C24—H24	119.4
C10—C9—H9B	111.2	C24—C25—C20	120.1 (3)
C8—C9—H9B	111.2	C24—C25—H25	119.9
H9A—C9—H9B	109.1	C20—C25—H25	119.9
N3—C10—C17	120.3 (2)	C23—C26—H26A	109.5
N3—C10—C9	114.3 (2)	C23—C26—H26B	109.5
C17—C10—C9	125.3 (2)	H26A—C26—H26B	109.5
C12—C11—C16	118.8 (2)	C23—C26—H26C	109.5
C12—C11—C8	122.7 (2)	H26A—C26—H26C	109.5
C16—C11—C8	118.5 (2)	H26B—C26—H26C	109.5
C7—N2—N3—C10	−168.49 (19)	C11—C12—C13—C14	−0.8 (4)
C8—N2—N3—C10	7.2 (2)	C12—C13—C14—C15	−0.5 (6)
C17—N4—N5—N6	−0.1 (2)	C12—C13—C14—F1	179.8 (3)
N4—N5—N6—C18	0.4 (3)	F1—C14—C15—C16	−179.6 (3)
N4—N5—N6—C20	−177.4 (2)	C13—C14—C15—C16	0.8 (7)
C7—N1—C1—C6	−5.6 (4)	C14—C15—C16—C11	0.2 (6)
C7—N1—C1—C2	172.6 (2)	C12—C11—C16—C15	−1.4 (4)
C6—C1—C2—C3	1.1 (3)	C8—C11—C16—C15	175.9 (3)
N1—C1—C2—C3	−177.3 (2)	N5—N4—C17—C18	−0.2 (3)
C1—C2—C3—C4	−0.5 (3)	N5—N4—C17—C10	175.68 (19)
C2—C3—C4—C5	−0.1 (4)	N3—C10—C17—N4	−172.65 (19)
C3—C4—C5—C6	0.3 (4)	C9—C10—C17—N4	3.8 (3)
C2—C1—C6—C5	−0.9 (3)	N3—C10—C17—C18	2.3 (3)
N1—C1—C6—C5	177.3 (2)	C9—C10—C17—C18	178.7 (2)
C4—C5—C6—C1	0.3 (4)	N5—N6—C18—C17	−0.5 (2)
C1—N1—C7—N2	−170.1 (2)	C20—N6—C18—C17	177.1 (2)
C1—N1—C7—S1	9.8 (4)	N5—N6—C18—C19	177.0 (2)
N3—N2—C7—N1	−3.3 (3)	C20—N6—C18—C19	−5.5 (4)
C8—N2—C7—N1	−178.33 (19)	N4—C17—C18—N6	0.4 (2)
N3—N2—C7—S1	176.78 (15)	C10—C17—C18—N6	−175.0 (2)
C8—N2—C7—S1	1.7 (3)	N4—C17—C18—C19	−176.8 (2)
C7—N2—C8—C11	−75.8 (3)	C10—C17—C18—C19	7.8 (4)
N3—N2—C8—C11	108.8 (2)	C18—N6—C20—C21	123.5 (3)
C7—N2—C8—C9	164.2 (2)	N5—N6—C20—C21	−59.1 (3)
N3—N2—C8—C9	−11.2 (2)	C18—N6—C20—C25	−56.8 (4)
N2—C8—C9—C10	10.3 (2)	N5—N6—C20—C25	120.5 (3)
C11—C8—C9—C10	−109.9 (2)	C25—C20—C21—C22	0.9 (4)
N2—N3—C10—C17	177.36 (18)	N6—C20—C21—C22	−179.5 (3)
N2—N3—C10—C9	0.6 (2)	C20—C21—C22—C23	−0.8 (5)
C8—C9—C10—N3	−7.4 (2)	C21—C22—C23—C24	0.5 (5)
C8—C9—C10—C17	175.99 (19)	C21—C22—C23—C26	−179.8 (3)
N2—C8—C11—C12	−18.8 (3)	C22—C23—C24—C25	−0.3 (5)
C9—C8—C11—C12	94.5 (3)	C26—C23—C24—C25	180.0 (3)
N2—C8—C11—C16	164.0 (2)	C23—C24—C25—C20	0.4 (6)
C9—C8—C11—C16	−82.8 (3)	C21—C20—C25—C24	−0.7 (5)
C16—C11—C12—C13	1.7 (4)	N6—C20—C25—C24	179.7 (3)
C8—C11—C12—C13	−175.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···N3	0.83 (3)	2.05 (3)	2.568 (3)	120 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H3⋯N3	0.83 (3)	2.05 (3)	2.568 (3)	120 (2)