Literature DB >> 22719413

4-[(E)-(4-Fluoro-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

H C Devarajegowda, S Jeyaseelan, R Sathishkumar, Agnes Sylvia D'souza, Alphonsus D'souza.   

Abstract

In the asymmetric unit of the title compound, C(10)H(9)FN(4)S, there are two independent mol-ecules in which the dihedral angles between the 1,2,4-triazole and benzene rings are 36.85 (10) and 7.81 (10)°. In the crystal, N-H⋯S inter-actions link pairs of independent mol-ecules into dimers. There are also π-π inter-actions between the triazole and benzene rings of inversion-related pairs of the more planar mol-ecule [centroid-centroid distance = 3.6430 (13) Å].

Entities:  

Year:  2012        PMID： 22719413      PMCID： PMC3379215          DOI： 10.1107/S1600536812019174

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background information on the properties and uses of chalcone derivatives, see: Temple (1981 ▶); Holla et al. (1998 ▶); Heidelberger et al. (1957 ▶); Andersson & MacGowan (2003 ▶). For a related structure, see: Devarajegowda et al. (2010 ▶).

Experimental

Crystal data

C10H9FN4S M = 236.27 Triclinic, a = 9.0048 (19) Å b = 10.811 (2) Å c = 12.729 (3) Å α = 101.205 (3)° β = 103.899 (3)° γ = 112.376 (3)° V = 1054.4 (4) Å3 Z = 4 Mo Kα radiation μ = 0.30 mm−1 T = 293 K 0.52 × 0.24 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.77, T max = 1.00 9923 measured reflections 3698 independent reflections 3383 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.085 S = 1.05 3698 reflections 291 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.28 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812019174/pk2403sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019174/pk2403Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812019174/pk2403Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C10H9FN4SZ = 4
Mr = 236.27F(000) = 488
Triclinic, P1Dx = 1.488 Mg m−3
Hall symbol: -P 1Melting point: 441 K
a = 9.0048 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.811 (2) ÅCell parameters from 3698 reflections
c = 12.729 (3) Åθ = 1.7–25.0°
α = 101.205 (3)°µ = 0.30 mm−1
β = 103.899 (3)°T = 293 K
γ = 112.376 (3)°Plate, colourless
V = 1054.4 (4) Å30.52 × 0.24 × 0.13 mm
Bruker SMART CCD area-detector diffractometer3698 independent reflections
Radiation source: fine-focus sealed tube3383 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω and φ scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)h = −10→10
Tmin = 0.77, Tmax = 1.00k = −12→12
9923 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0428P)2 + 0.5511P] where P = (Fo2 + 2Fc2)/3
3698 reflections(Δ/σ)max = 0.001
291 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.
xyzUiso*/Ueq
S1A0.23713 (5)0.62340 (4)0.35429 (3)0.01697 (12)
F2A1.06962 (13)0.90655 (11)0.94413 (8)0.0227 (2)
N4A0.40671 (18)0.90351 (15)0.20331 (12)0.0173 (3)
N3A0.29189 (18)0.78138 (15)0.21256 (12)0.0156 (3)
H3A0.19390.72640.16030.019*
N5A0.50787 (17)0.86716 (14)0.36491 (11)0.0143 (3)
N6A0.62298 (17)0.90901 (15)0.47624 (11)0.0158 (3)
C7A0.6964 (2)1.08701 (19)0.33309 (15)0.0229 (4)
H7A10.68941.13250.27560.034*
H7A20.79201.06580.34200.034*
H7A30.71121.14860.40420.034*
C8A0.5365 (2)0.95448 (18)0.29812 (14)0.0168 (4)
C9A0.3462 (2)0.75585 (17)0.31005 (14)0.0137 (3)
C10A0.6362 (2)0.80838 (17)0.51028 (14)0.0147 (3)
H10A0.57240.71580.46170.018*
C11A0.7512 (2)0.83788 (17)0.62529 (14)0.0141 (3)
C12A0.7622 (2)0.72535 (18)0.65853 (14)0.0156 (4)
H12A0.69680.63410.60780.019*
C13A0.8693 (2)0.74710 (18)0.76628 (14)0.0164 (4)
H13A0.87640.67200.78860.020*
C14A0.9647 (2)0.88390 (18)0.83872 (14)0.0168 (4)
C15A0.9588 (2)0.99895 (18)0.80954 (14)0.0188 (4)
H15A1.02571.08990.86070.023*
C16A0.8504 (2)0.97526 (18)0.70181 (14)0.0166 (4)
H16A0.84371.05100.68040.020*
S1B−0.10121 (5)0.62370 (4)0.02884 (3)0.01602 (12)
F2B−0.99250 (12)0.36565 (11)−0.53412 (8)0.0211 (2)
N3B−0.14587 (17)0.43278 (14)0.14306 (12)0.0154 (3)
H3B−0.04360.48010.19190.018*
N4B−0.26081 (18)0.30629 (15)0.14576 (12)0.0167 (3)
N5B−0.37235 (17)0.36840 (14)0.00279 (11)0.0134 (3)
N6B−0.50533 (17)0.34307 (15)−0.09421 (11)0.0154 (3)
C7B−0.5645 (2)0.14351 (18)0.02702 (15)0.0201 (4)
H7B1−0.55610.09040.07860.030*
H7B2−0.59400.0854−0.04940.030*
H7B3−0.65130.17340.03070.030*
C8B−0.3976 (2)0.26907 (18)0.05969 (14)0.0154 (4)
C9B−0.2066 (2)0.47588 (17)0.05816 (13)0.0137 (3)
C10B−0.4876 (2)0.43797 (18)−0.14289 (14)0.0157 (4)
H10B−0.38740.5224−0.11320.019*
C11B−0.6245 (2)0.41410 (18)−0.24528 (14)0.0152 (4)
C12B−0.6015 (2)0.52269 (18)−0.29298 (14)0.0163 (4)
H12B−0.50090.6067−0.25890.020*
C13B−0.7250 (2)0.50845 (18)−0.39004 (14)0.0165 (4)
H13B−0.70920.5812−0.42160.020*
C14B−0.8721 (2)0.38242 (18)−0.43791 (13)0.0159 (4)
C15B−0.9013 (2)0.27145 (18)−0.39334 (14)0.0175 (4)
H15B−1.00240.1880−0.42790.021*
C16B−0.7764 (2)0.28784 (18)−0.29615 (14)0.0162 (4)
H16B−0.79350.2150−0.26470.019*
U11U22U33U12U13U23
S1A0.0138 (2)0.0175 (2)0.0161 (2)0.00357 (18)0.00235 (17)0.00864 (17)
F2A0.0208 (5)0.0240 (6)0.0141 (5)0.0056 (5)−0.0019 (4)0.0066 (4)
N4A0.0152 (7)0.0167 (7)0.0181 (7)0.0047 (6)0.0043 (6)0.0086 (6)
N3A0.0116 (7)0.0161 (7)0.0145 (7)0.0036 (6)0.0005 (6)0.0059 (6)
N5A0.0136 (7)0.0137 (7)0.0130 (7)0.0050 (6)0.0014 (6)0.0055 (6)
N6A0.0132 (7)0.0180 (7)0.0117 (7)0.0048 (6)0.0003 (6)0.0052 (6)
C7A0.0201 (9)0.0191 (9)0.0216 (9)0.0021 (8)0.0022 (8)0.0105 (8)
C8A0.0169 (9)0.0182 (9)0.0166 (8)0.0080 (7)0.0051 (7)0.0089 (7)
C9A0.0131 (8)0.0153 (8)0.0126 (8)0.0074 (7)0.0030 (7)0.0041 (6)
C10A0.0126 (8)0.0150 (8)0.0151 (8)0.0045 (7)0.0050 (7)0.0045 (7)
C11A0.0110 (8)0.0176 (8)0.0131 (8)0.0051 (7)0.0047 (7)0.0055 (7)
C12A0.0134 (8)0.0152 (8)0.0152 (8)0.0047 (7)0.0037 (7)0.0035 (7)
C13A0.0175 (9)0.0167 (9)0.0170 (8)0.0083 (7)0.0058 (7)0.0086 (7)
C14A0.0137 (8)0.0233 (9)0.0107 (8)0.0060 (7)0.0024 (7)0.0069 (7)
C15A0.0193 (9)0.0157 (9)0.0149 (8)0.0034 (7)0.0043 (7)0.0023 (7)
C16A0.0196 (9)0.0161 (9)0.0170 (8)0.0088 (7)0.0073 (7)0.0084 (7)
S1B0.0125 (2)0.0161 (2)0.0166 (2)0.00421 (17)0.00188 (17)0.00781 (17)
F2B0.0166 (5)0.0258 (6)0.0163 (5)0.0081 (4)−0.0012 (4)0.0089 (4)
N3B0.0105 (7)0.0172 (7)0.0151 (7)0.0040 (6)0.0015 (6)0.0066 (6)
N4B0.0151 (7)0.0184 (7)0.0168 (7)0.0067 (6)0.0050 (6)0.0081 (6)
N5B0.0114 (7)0.0147 (7)0.0118 (7)0.0051 (6)0.0013 (6)0.0047 (6)
N6B0.0135 (7)0.0191 (7)0.0119 (7)0.0080 (6)0.0009 (6)0.0044 (6)
C7B0.0181 (9)0.0181 (9)0.0191 (9)0.0040 (7)0.0028 (7)0.0089 (7)
C8B0.0184 (9)0.0173 (9)0.0136 (8)0.0092 (7)0.0070 (7)0.0074 (7)
C9B0.0132 (8)0.0165 (8)0.0127 (8)0.0081 (7)0.0043 (7)0.0048 (7)
C10B0.0131 (8)0.0175 (9)0.0150 (8)0.0063 (7)0.0032 (7)0.0052 (7)
C11B0.0142 (8)0.0192 (9)0.0135 (8)0.0089 (7)0.0047 (7)0.0051 (7)
C12B0.0129 (8)0.0173 (9)0.0154 (8)0.0042 (7)0.0044 (7)0.0045 (7)
C13B0.0186 (9)0.0187 (9)0.0161 (8)0.0099 (7)0.0069 (7)0.0092 (7)
C14B0.0126 (8)0.0244 (9)0.0106 (8)0.0097 (7)0.0018 (7)0.0054 (7)
C15B0.0135 (8)0.0170 (9)0.0176 (9)0.0039 (7)0.0037 (7)0.0046 (7)
C16B0.0164 (9)0.0186 (9)0.0158 (8)0.0085 (7)0.0060 (7)0.0079 (7)
S1A—C9A1.6854 (17)S1B—C9B1.6855 (17)
F2A—C14A1.3564 (19)F2B—C14B1.3545 (18)
N4A—C8A1.304 (2)N3B—C9B1.338 (2)
N4A—N3A1.3805 (19)N3B—N4B1.3785 (19)
N3A—C9A1.341 (2)N3B—H3B0.8600
N3A—H3A0.8600N4B—C8B1.297 (2)
N5A—C9A1.381 (2)N5B—C8B1.387 (2)
N5A—C8A1.383 (2)N5B—C9B1.390 (2)
N5A—N6A1.4055 (18)N5B—N6B1.3935 (18)
N6A—C10A1.282 (2)N6B—C10B1.277 (2)
C7A—C8A1.482 (2)C7B—C8B1.484 (2)
C7A—H7A10.9600C7B—H7B10.9600
C7A—H7A20.9600C7B—H7B20.9600
C7A—H7A30.9600C7B—H7B30.9600
C10A—C11A1.468 (2)C10B—C11B1.463 (2)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.393 (2)C11B—C12B1.394 (2)
C11A—C16A1.401 (2)C11B—C16B1.401 (2)
C12A—C13A1.390 (2)C12B—C13B1.387 (2)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.378 (2)C13B—C14B1.377 (2)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.381 (2)C14B—C15B1.388 (2)
C15A—C16A1.389 (2)C15B—C16B1.386 (2)
C15A—H15A0.9300C15B—H15B0.9300
C16A—H16A0.9300C16B—H16B0.9300
C8A—N4A—N3A103.69 (13)C9B—N3B—N4B114.48 (13)
C9A—N3A—N4A114.26 (13)C9B—N3B—H3B122.8
C9A—N3A—H3A122.9N4B—N3B—H3B122.8
N4A—N3A—H3A122.9C8B—N4B—N3B104.14 (13)
C9A—N5A—C8A108.36 (13)C8B—N5B—C9B108.24 (13)
C9A—N5A—N6A130.31 (14)C8B—N5B—N6B118.40 (13)
C8A—N5A—N6A120.57 (13)C9B—N5B—N6B133.34 (14)
C10A—N6A—N5A115.20 (14)C10B—N6B—N5B118.87 (14)
C8A—C7A—H7A1109.5C8B—C7B—H7B1109.5
C8A—C7A—H7A2109.5C8B—C7B—H7B2109.5
H7A1—C7A—H7A2109.5H7B1—C7B—H7B2109.5
C8A—C7A—H7A3109.5C8B—C7B—H7B3109.5
H7A1—C7A—H7A3109.5H7B1—C7B—H7B3109.5
H7A2—C7A—H7A3109.5H7B2—C7B—H7B3109.5
N4A—C8A—N5A110.95 (15)N4B—C8B—N5B110.75 (15)
N4A—C8A—C7A126.29 (15)N4B—C8B—C7B126.55 (15)
N5A—C8A—C7A122.75 (15)N5B—C8B—C7B122.61 (14)
N3A—C9A—N5A102.69 (14)N3B—C9B—N5B102.39 (14)
N3A—C9A—S1A127.58 (13)N3B—C9B—S1B127.11 (13)
N5A—C9A—S1A129.68 (12)N5B—C9B—S1B130.49 (12)
N6A—C10A—C11A120.60 (15)N6B—C10B—C11B120.14 (15)
N6A—C10A—H10A119.7N6B—C10B—H10B119.9
C11A—C10A—H10A119.7C11B—C10B—H10B119.9
C12A—C11A—C16A119.27 (15)C12B—C11B—C16B119.26 (15)
C12A—C11A—C10A118.67 (15)C12B—C11B—C10B117.97 (15)
C16A—C11A—C10A122.06 (15)C16B—C11B—C10B122.77 (15)
C13A—C12A—C11A121.16 (15)C13B—C12B—C11B121.55 (16)
C13A—C12A—H12A119.4C13B—C12B—H12B119.2
C11A—C12A—H12A119.4C11B—C12B—H12B119.2
C14A—C13A—C12A117.62 (15)C14B—C13B—C12B117.43 (16)
C14A—C13A—H13A121.2C14B—C13B—H13B121.3
C12A—C13A—H13A121.2C12B—C13B—H13B121.3
F2A—C14A—C13A118.21 (15)F2B—C14B—C13B118.19 (15)
F2A—C14A—C15A118.41 (15)F2B—C14B—C15B118.62 (15)
C13A—C14A—C15A123.38 (15)C13B—C14B—C15B123.18 (15)
C14A—C15A—C16A118.25 (16)C16B—C15B—C14B118.52 (16)
C14A—C15A—H15A120.9C16B—C15B—H15B120.7
C16A—C15A—H15A120.9C14B—C15B—H15B120.7
C15A—C16A—C11A120.32 (16)C15B—C16B—C11B120.06 (16)
C15A—C16A—H16A119.8C15B—C16B—H16B120.0
C11A—C16A—H16A119.8C11B—C16B—H16B120.0
C8A—N4A—N3A—C9A0.33 (18)C9B—N3B—N4B—C8B0.09 (18)
C9A—N5A—N6A—C10A42.7 (2)C8B—N5B—N6B—C10B175.50 (14)
C8A—N5A—N6A—C10A−148.60 (15)C9B—N5B—N6B—C10B−6.8 (3)
N3A—N4A—C8A—N5A1.13 (18)N3B—N4B—C8B—N5B−0.02 (18)
N3A—N4A—C8A—C7A−179.27 (17)N3B—N4B—C8B—C7B−176.50 (16)
C9A—N5A—C8A—N4A−2.17 (19)C9B—N5B—C8B—N4B−0.05 (19)
N6A—N5A—C8A—N4A−173.13 (14)N6B—N5B—C8B—N4B178.23 (13)
C9A—N5A—C8A—C7A178.21 (16)C9B—N5B—C8B—C7B176.60 (15)
N6A—N5A—C8A—C7A7.2 (2)N6B—N5B—C8B—C7B−5.1 (2)
N4A—N3A—C9A—N5A−1.58 (18)N4B—N3B—C9B—N5B−0.11 (17)
N4A—N3A—C9A—S1A176.05 (12)N4B—N3B—C9B—S1B−179.39 (12)
C8A—N5A—C9A—N3A2.17 (17)C8B—N5B—C9B—N3B0.09 (17)
N6A—N5A—C9A—N3A171.95 (15)N6B—N5B—C9B—N3B−177.83 (15)
C8A—N5A—C9A—S1A−175.39 (13)C8B—N5B—C9B—S1B179.34 (13)
N6A—N5A—C9A—S1A−5.6 (3)N6B—N5B—C9B—S1B1.4 (3)
N5A—N6A—C10A—C11A−179.52 (13)N5B—N6B—C10B—C11B179.62 (14)
N6A—C10A—C11A—C12A−179.68 (15)N6B—C10B—C11B—C12B177.84 (15)
N6A—C10A—C11A—C16A−0.1 (2)N6B—C10B—C11B—C16B−1.8 (3)
C16A—C11A—C12A—C13A0.2 (2)C16B—C11B—C12B—C13B−0.4 (2)
C10A—C11A—C12A—C13A179.80 (15)C10B—C11B—C12B—C13B179.94 (15)
C11A—C12A—C13A—C14A−0.3 (2)C11B—C12B—C13B—C14B0.0 (2)
C12A—C13A—C14A—F2A179.92 (14)C12B—C13B—C14B—F2B−178.64 (14)
C12A—C13A—C14A—C15A0.0 (3)C12B—C13B—C14B—C15B0.3 (3)
F2A—C14A—C15A—C16A−179.57 (14)F2B—C14B—C15B—C16B178.77 (14)
C13A—C14A—C15A—C16A0.4 (3)C13B—C14B—C15B—C16B−0.2 (3)
C14A—C15A—C16A—C11A−0.4 (2)C14B—C15B—C16B—C11B−0.2 (2)
C12A—C11A—C16A—C15A0.1 (2)C12B—C11B—C16B—C15B0.5 (2)
C10A—C11A—C16A—C15A−179.41 (15)C10B—C11B—C16B—C15B−179.81 (16)
D—H···AD—HH···AD···AD—H···A
N3A—H3A···S1B0.862.453.2840 (18)164
N3B—H3B···S1A0.862.513.3691 (18)172
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N3A—H3A⋯S1B0.862.453.2840 (18)164
N3B—H3B⋯S1A0.862.513.3691 (18)172
  3 in total

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Authors:  C HEIDELBERGER; N K CHAUDHURI; P DANNEBERG; D MOOREN; L GRIESBACH; R DUSCHINSKY; R J SCHNITZER; E PLEVEN; J SCHEINER
Journal:  Nature       Date:  1957-03-30       Impact factor: 49.962

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  1-{1-[2,8-Bis(trifluoro-meth-yl)-4-quin-olyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone.

Authors:  H C Devarajegowda; S Jeyaseelan; V Sumangala; Suresh P Nayak
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-08
  3 in total
  5 in total

1.  The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thio-nes, including a second polymorph of 4-[(E)-(5-bromo-2-hy-droxy-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Authors:  Padmanabha S Manjula; Balladka K Sarojini; Hemmige S Yathirajan; Mehmet Akkurt; Cem Cüneyt Ersanlı; Christopher Glidewell
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-08-06

2.  3-Methyl-4-{(E)-[4-(methyl-sulfan-yl)benzyl-idene]amino}-1H-1,2,4-triazole-5(4H)-thione.

Authors:  B K Sarojini; P S Manjula; Gurumurthy Hegde; Dalbir Kour; Vivek K Gupta; Rajni Kant
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-04-13

3.  1-(4-Chloro-phen-yl)-1H-1,2,4-triazol-5(4H)-one.

Authors:  Pramod P Kattimani; Ravindra R Kamble; Mahadev N Kumbar; H K Arunkashi; H C Devarajegowda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-03-29

4.  4-[(E)-(4-Chloro-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Authors:  B K Sarojini; P S Manjula; Manpreet Kaur; Brian J Anderson; Jerry P Jasinski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-12-14

5.  4-[(E)-(4-Hy-droxy-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Authors:  Balladka K Sarojini; Padmanabha S Manjula; B Narayana; Jerry P Jasinski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-05-31
  5 in total

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