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In the title compound, C15H19N5OS, the morpholine ring adopts a chair conformation. The mean plane of the pyridine ring makes a dihedral angle of 35.16 (7)° with the triazole ring plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015953/ob6523sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015953/ob6523Isup2.hkl
Contains datablock I

CCDC reference: 274609

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.115
  • Data-to-parameter ratio = 22.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C1 .. 6.78 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

4-Allyl-2-(morpholin-4-ylmethyl)-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4- triazole-3-thione top
Crystal data top
C15H19N5OSZ = 2
Mr = 317.41F(000) = 336
Triclinic, P1Dx = 1.242 Mg m3
Hall symbol: -P 1Melting point: 407 K
a = 8.9387 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1043 (7) ÅCell parameters from 11208 reflections
c = 10.6069 (8) Åθ = 1.9–29.0°
α = 88.509 (6)°µ = 0.20 mm1
β = 85.498 (6)°T = 296 K
γ = 80.661 (6)°Prism, colourless
V = 849.05 (11) Å30.62 × 0.42 × 0.20 mm
Data collection top
Stoe IPDS-2
diffractometer
4462 independent reflections
Radiation source: sealed X-ray tube3716 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.034
Detector resolution: 6.67 pixels mm-1θmax = 29.0°, θmin = 1.9°
ω scansh = 1212
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1212
Tmin = 0.886, Tmax = 0.967l = 1413
11655 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.0942P]
where P = (Fo2 + 2Fc2)/3
4462 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. Melting points were determined in open capillary tubes on a digital Gallenkamp melting point apparatus and are uncorrected. The IR spectra were recorded for KBr disks with a Mattson 1000 F T—IR spectrometer. 1H-NMR spectra were recorded at room temperature on a Varian-Mercury-Plus 400 MHz 1H-NMR, 100 MHz 13C-NMR spectrometer in DMSO-d6 with TMS as an internal standard. Starting materials was obtained from Fluka or Aldrich.

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
xyzUiso*/Ueq
S10.03503 (4)0.27711 (4)0.37723 (3)0.05186 (11)
O10.66113 (13)0.04294 (12)0.33480 (15)0.0767 (4)
N10.32526 (11)0.39491 (11)0.59419 (9)0.0406 (2)
N20.27940 (11)0.35900 (11)0.48007 (9)0.0392 (2)
N30.49030 (11)0.24709 (11)0.33066 (10)0.0437 (2)
N40.09693 (11)0.33029 (10)0.61769 (9)0.0391 (2)
N50.23554 (18)0.4652 (2)1.06510 (12)0.0739 (4)
C10.13896 (13)0.32053 (12)0.49046 (11)0.0392 (2)
C20.21296 (13)0.37622 (12)0.67545 (11)0.0394 (2)
C30.37869 (13)0.37358 (13)0.36387 (11)0.0416 (2)
H3A0.31480.39670.29390.050*
H3B0.43070.45780.37340.050*
C40.42821 (17)0.11901 (16)0.29056 (16)0.0574 (3)
H4A0.36020.14890.22430.069*
H4B0.37060.07970.36130.069*
C50.5569 (2)0.0006 (2)0.2421 (2)0.0767 (5)
H5A0.51570.08550.21710.092*
H5B0.60970.03850.16800.092*
C60.72175 (17)0.08196 (18)0.37334 (19)0.0657 (4)
H6A0.77750.12130.30150.079*
H6B0.79250.05070.43730.079*
C70.59922 (15)0.20232 (16)0.42568 (14)0.0527 (3)
H7A0.54770.16600.50120.063*
H7B0.64380.28730.44840.063*
C80.21695 (14)0.40488 (14)0.81040 (11)0.0437 (3)
C90.28993 (17)0.51899 (18)0.84571 (13)0.0560 (3)
H90.33300.57850.78510.067*
C100.2971 (2)0.5420 (2)0.97280 (15)0.0702 (4)
H100.34890.61690.99540.084*
C110.1662 (2)0.3566 (2)1.02984 (14)0.0698 (4)
H110.12200.30091.09280.084*
C120.15527 (18)0.32091 (18)0.90553 (13)0.0579 (3)
H120.10740.24190.88610.070*
C130.05649 (14)0.31609 (15)0.67084 (13)0.0474 (3)
H13A0.12920.35710.61080.057*
H13B0.07920.37420.74730.057*
C140.07525 (16)0.15867 (17)0.70120 (16)0.0576 (3)
H140.03630.08740.64090.069*
C150.1411 (3)0.1136 (3)0.8043 (2)0.1020 (8)
H15A0.18150.18140.86690.122*
H15B0.14810.01330.81590.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.04829 (19)0.0632 (2)0.04683 (18)0.01327 (14)0.00996 (13)0.00649 (14)
O10.0574 (6)0.0486 (6)0.1213 (11)0.0014 (5)0.0083 (7)0.0083 (6)
N10.0417 (5)0.0438 (5)0.0370 (5)0.0085 (4)0.0034 (4)0.0035 (4)
N20.0399 (5)0.0430 (5)0.0353 (4)0.0080 (4)0.0023 (4)0.0027 (4)
N30.0414 (5)0.0424 (5)0.0467 (5)0.0054 (4)0.0006 (4)0.0029 (4)
N40.0371 (5)0.0402 (5)0.0396 (5)0.0055 (4)0.0000 (4)0.0025 (4)
N50.0766 (9)0.1045 (11)0.0407 (6)0.0132 (8)0.0049 (6)0.0106 (7)
C10.0387 (5)0.0379 (5)0.0403 (5)0.0042 (4)0.0025 (4)0.0014 (4)
C20.0414 (5)0.0384 (5)0.0381 (5)0.0054 (4)0.0024 (4)0.0020 (4)
C30.0440 (6)0.0417 (6)0.0381 (5)0.0063 (4)0.0009 (4)0.0010 (4)
C40.0507 (7)0.0509 (7)0.0712 (9)0.0062 (6)0.0082 (6)0.0125 (6)
C50.0652 (10)0.0601 (9)0.1039 (14)0.0037 (7)0.0046 (9)0.0315 (9)
C60.0453 (7)0.0587 (8)0.0920 (12)0.0033 (6)0.0077 (7)0.0038 (8)
C70.0459 (7)0.0524 (7)0.0601 (8)0.0066 (5)0.0086 (6)0.0014 (6)
C80.0437 (6)0.0486 (6)0.0374 (5)0.0040 (5)0.0015 (4)0.0027 (5)
C90.0603 (8)0.0658 (8)0.0445 (7)0.0189 (6)0.0016 (6)0.0089 (6)
C100.0722 (10)0.0910 (12)0.0521 (8)0.0246 (9)0.0034 (7)0.0221 (8)
C110.0779 (11)0.0904 (12)0.0405 (7)0.0148 (9)0.0007 (7)0.0071 (7)
C120.0680 (9)0.0637 (8)0.0437 (7)0.0164 (7)0.0033 (6)0.0049 (6)
C130.0383 (6)0.0507 (7)0.0515 (7)0.0048 (5)0.0045 (5)0.0054 (5)
C140.0505 (7)0.0555 (8)0.0681 (9)0.0156 (6)0.0050 (6)0.0061 (6)
C150.1258 (19)0.0818 (13)0.1032 (16)0.0520 (13)0.0373 (14)0.0088 (11)
Geometric parameters (Å, º) top
S1—C11.6676 (12)C5—H5B0.9700
O1—C51.413 (2)C6—C71.502 (2)
O1—C61.419 (2)C6—H6A0.9700
N1—C21.3006 (15)C6—H6B0.9700
N1—N21.3719 (13)C7—H7A0.9700
N2—C11.3526 (15)C7—H7B0.9700
N2—C31.4773 (15)C8—C121.3841 (19)
N3—C31.4278 (15)C8—C91.3870 (19)
N3—C41.4566 (17)C9—C101.378 (2)
N3—C71.4607 (16)C9—H90.9300
N4—C21.3711 (14)C10—H100.9300
N4—C11.3734 (15)C11—C121.381 (2)
N4—C131.4654 (15)C11—H110.9300
N5—C101.325 (2)C12—H120.9300
N5—C111.325 (2)C13—C141.494 (2)
C2—C81.4658 (16)C13—H13A0.9700
C3—H3A0.9700C13—H13B0.9700
C3—H3B0.9700C14—C151.290 (3)
C4—C51.511 (2)C14—H140.9300
C4—H4A0.9700C15—H15A0.9300
C4—H4B0.9700C15—H15B0.9300
C5—H5A0.9700
C5—O1—C6110.12 (13)C7—C6—H6A109.3
C2—N1—N2104.48 (9)O1—C6—H6B109.3
C1—N2—N1112.54 (9)C7—C6—H6B109.3
C1—N2—C3128.11 (10)H6A—C6—H6B107.9
N1—N2—C3119.25 (9)N3—C7—C6109.42 (13)
C3—N3—C4114.41 (10)N3—C7—H7A109.8
C3—N3—C7114.45 (10)C6—C7—H7A109.8
C4—N3—C7110.46 (11)N3—C7—H7B109.8
C2—N4—C1107.67 (9)C6—C7—H7B109.8
C2—N4—C13128.90 (10)H7A—C7—H7B108.2
C1—N4—C13122.71 (10)C12—C8—C9117.78 (12)
C10—N5—C11116.20 (14)C12—C8—C2123.39 (12)
N2—C1—N4103.84 (10)C9—C8—C2118.81 (12)
N2—C1—S1129.21 (9)C10—C9—C8118.33 (14)
N4—C1—S1126.92 (9)C10—C9—H9120.8
N1—C2—N4111.46 (10)C8—C9—H9120.8
N1—C2—C8121.61 (11)N5—C10—C9124.72 (16)
N4—C2—C8126.92 (11)N5—C10—H10117.6
N3—C3—N2116.37 (9)C9—C10—H10117.6
N3—C3—H3A108.2N5—C11—C12124.15 (16)
N2—C3—H3A108.2N5—C11—H11117.9
N3—C3—H3B108.2C12—C11—H11117.9
N2—C3—H3B108.2C11—C12—C8118.78 (15)
H3A—C3—H3B107.3C11—C12—H12120.6
N3—C4—C5109.31 (12)C8—C12—H12120.6
N3—C4—H4A109.8N4—C13—C14112.99 (11)
C5—C4—H4A109.8N4—C13—H13A109.0
N3—C4—H4B109.8C14—C13—H13A109.0
C5—C4—H4B109.8N4—C13—H13B109.0
H4A—C4—H4B108.3C14—C13—H13B109.0
O1—C5—C4111.61 (15)H13A—C13—H13B107.8
O1—C5—H5A109.3C15—C14—C13125.31 (17)
C4—C5—H5A109.3C15—C14—H14117.3
O1—C5—H5B109.3C13—C14—H14117.3
C4—C5—H5B109.3C14—C15—H15A120.0
H5A—C5—H5B108.0C14—C15—H15B120.0
O1—C6—C7111.77 (12)H15A—C15—H15B120.0
O1—C6—H6A109.3
C2—N1—N2—C10.90 (13)C6—O1—C5—C458.5 (2)
C2—N1—N2—C3177.63 (10)N3—C4—C5—O157.8 (2)
N1—N2—C1—N41.19 (12)C5—O1—C6—C758.5 (2)
C3—N2—C1—N4177.56 (10)C3—N3—C7—C6172.69 (11)
N1—N2—C1—S1176.71 (9)C4—N3—C7—C656.45 (15)
C3—N2—C1—S10.35 (18)O1—C6—C7—N357.51 (18)
C2—N4—C1—N21.00 (12)N1—C2—C8—C12143.98 (14)
C13—N4—C1—N2172.10 (10)N4—C2—C8—C1236.94 (19)
C2—N4—C1—S1176.97 (9)N1—C2—C8—C934.04 (18)
C13—N4—C1—S15.87 (16)N4—C2—C8—C9145.04 (13)
N2—N1—C2—N40.21 (12)C12—C8—C9—C100.1 (2)
N2—N1—C2—C8179.43 (10)C2—C8—C9—C10178.02 (14)
C1—N4—C2—N10.51 (13)C11—N5—C10—C91.8 (3)
C13—N4—C2—N1170.88 (11)C8—C9—C10—N51.9 (3)
C1—N4—C2—C8178.65 (11)C10—N5—C11—C120.0 (3)
C13—N4—C2—C88.28 (19)N5—C11—C12—C81.6 (3)
C4—N3—C3—N268.69 (15)C9—C8—C12—C111.5 (2)
C7—N3—C3—N260.22 (14)C2—C8—C12—C11179.51 (14)
C1—N2—C3—N395.79 (14)C2—N4—C13—C14102.89 (15)
N1—N2—C3—N388.06 (13)C1—N4—C13—C1488.03 (15)
C3—N3—C4—C5172.69 (13)N4—C13—C14—C15134.8 (2)
C7—N3—C4—C556.43 (17)
 

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