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In the title compound, C12H19N3OS, the 2,6-dimethyl­morpholine ring, which is in a chair conformation, and the planar 3,5-dimethyl­pyrazole ring are linked at an angle of 114.2 (3)° by the methane­thione group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026730/ez2013sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026730/ez2013Isup2.hkl
Contains datablock I

CCDC reference: 618193

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.081
  • wR factor = 0.248
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.06 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. N12 .. 2.74 Ang.
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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).

2,6-Dimethylmorpholin-4-yl 3,5-dimethyl-1H-pyrazole thioketone top
Crystal data top
C12H19N3OSZ = 2
Mr = 253.37F(000) = 272
Triclinic, P1Dx = 1.215 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 5.242 (2) ÅCell parameters from 25 reflections
b = 11.209 (2) Åθ = 13.1–43.8°
c = 12.082 (2) ŵ = 1.99 mm1
α = 83.30 (2)°T = 297 K
β = 80.62 (2)°Prism, colourless
γ = 83.66 (2)°0.30 × 0.22 × 0.08 mm
V = 692.6 (3) Å3
Data collection top
Enraf–Nonius CAD4
diffractometer
1997 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 67.9°, θmin = 3.7°
non–profiled ω/2θ scansh = 66
Absorption correction: ψ scan
(North et al., 1968)
k = 1313
Tmin = 0.587, Tmax = 0.857l = 114
2875 measured reflections2 standard reflections every 120 min
2507 independent reflections intensity decay: 3%
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.1279P)2 + 0.6447P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.081(Δ/σ)max < 0.001
wR(F2) = 0.248Δρmax = 0.72 e Å3
S = 1.04Δρmin = 0.35 e Å3
2507 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
155 parametersExtinction coefficient: 0.070 (7)
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S91.0113 (4)0.79575 (11)0.53249 (10)0.1128 (7)
O10.3537 (5)0.9903 (2)0.8427 (2)0.0681 (8)
N40.7476 (7)0.8366 (3)0.7328 (3)0.0722 (10)
N110.9181 (6)0.6407 (2)0.7125 (2)0.0548 (7)
N121.0743 (6)0.6174 (3)0.7959 (2)0.0601 (8)
C20.3596 (9)0.8630 (4)0.8736 (4)0.0767 (12)
H20.25040.82960.82850.092*
C30.6247 (9)0.8038 (4)0.8501 (4)0.0795 (12)
H3A0.61910.71700.86280.095*
H3B0.72930.82710.90190.095*
C50.7272 (10)0.9686 (4)0.7033 (4)0.0882 (14)
H5A0.83631.00490.74510.106*
H5B0.78890.98640.62360.106*
C60.4612 (10)1.0203 (4)0.7291 (4)0.0855 (14)
H60.35860.98590.68190.103*
C70.2456 (9)0.8420 (4)0.9941 (4)0.0775 (12)
H7A0.07320.88201.00550.116*
H7B0.35110.87331.03980.116*
H7C0.23860.75691.01490.116*
C80.8801 (7)0.7615 (3)0.6630 (3)0.0591 (9)
C100.4272 (12)1.1545 (4)0.7041 (5)0.0999 (17)
H10A0.24731.18260.72300.150*
H10B0.48391.17610.62540.150*
H10C0.52851.19100.74800.150*
C131.1001 (7)0.4983 (3)0.8138 (3)0.0577 (9)
C140.9634 (7)0.4467 (3)0.7445 (3)0.0628 (9)
H140.95210.36480.74280.075*
C150.8498 (7)0.5383 (3)0.6802 (3)0.0551 (8)
C161.2626 (9)0.4377 (4)0.8985 (4)0.0791 (12)
H16A1.33190.49760.93270.119*0.50
H16B1.40270.38690.86170.119*0.50
H16C1.15780.38970.95550.119*0.50
H16D1.26300.35180.90060.119*0.50
H16E1.19220.46260.97150.119*0.50
H16F1.43720.45980.87780.119*0.50
C170.6788 (9)0.5386 (4)0.5933 (4)0.0764 (11)
H17A0.63330.62030.56420.115*0.50
H17B0.52390.50170.62660.115*0.50
H17C0.76870.49420.53300.115*0.50
H17D0.65060.45720.58500.115*0.50
H17E0.76000.57570.52260.115*0.50
H17F0.51520.58320.61620.115*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S90.1816 (16)0.0683 (8)0.0662 (8)0.0073 (8)0.0253 (8)0.0066 (5)
O10.0775 (17)0.0524 (14)0.0706 (16)0.0091 (11)0.0090 (13)0.0084 (11)
N40.078 (2)0.0450 (16)0.079 (2)0.0109 (14)0.0104 (17)0.0071 (14)
N110.0676 (18)0.0441 (14)0.0516 (15)0.0023 (12)0.0114 (13)0.0042 (11)
N120.0687 (18)0.0545 (16)0.0583 (17)0.0027 (13)0.0198 (14)0.0042 (13)
C20.093 (3)0.058 (2)0.073 (2)0.0017 (19)0.002 (2)0.0060 (18)
C30.086 (3)0.064 (2)0.076 (3)0.008 (2)0.004 (2)0.0071 (19)
C50.098 (3)0.051 (2)0.100 (3)0.007 (2)0.008 (3)0.010 (2)
C60.109 (4)0.058 (2)0.078 (3)0.018 (2)0.004 (2)0.001 (2)
C70.078 (3)0.078 (3)0.072 (2)0.000 (2)0.000 (2)0.010 (2)
C80.068 (2)0.0479 (18)0.059 (2)0.0006 (15)0.0116 (16)0.0003 (15)
C100.124 (4)0.057 (2)0.103 (4)0.028 (2)0.003 (3)0.004 (2)
C130.0591 (19)0.0525 (18)0.0551 (19)0.0071 (15)0.0018 (15)0.0007 (14)
C140.067 (2)0.0440 (17)0.075 (2)0.0011 (15)0.0048 (18)0.0082 (16)
C150.0559 (18)0.0518 (18)0.0569 (18)0.0006 (14)0.0047 (15)0.0122 (14)
C160.077 (3)0.081 (3)0.073 (3)0.019 (2)0.017 (2)0.004 (2)
C170.076 (3)0.081 (3)0.077 (3)0.002 (2)0.021 (2)0.018 (2)
Geometric parameters (Å, º) top
S9—C81.634 (4)C7—H7C0.9600
O1—C61.414 (5)C10—H10A0.9600
O1—C21.430 (5)C10—H10B0.9600
N4—C81.322 (5)C10—H10C0.9600
N4—C51.477 (5)C13—C141.396 (5)
N4—C31.481 (5)C13—C161.493 (5)
N11—C151.356 (4)C14—C151.357 (5)
N11—N121.383 (4)C14—H140.9300
N11—C81.422 (4)C15—C171.487 (5)
N12—C131.322 (4)C16—H16A0.9600
C2—C31.471 (6)C16—H16B0.9600
C2—C71.483 (6)C16—H16C0.9600
C2—H20.9800C16—H16D0.9600
C3—H3A0.9700C16—H16E0.9600
C3—H3B0.9700C16—H16F0.9600
C5—C61.449 (6)C17—H17A0.9600
C5—H5A0.9700C17—H17B0.9600
C5—H5B0.9700C17—H17C0.9600
C6—C101.496 (6)C17—H17D0.9600
C6—H60.9800C17—H17E0.9600
C7—H7A0.9600C17—H17F0.9600
C7—H7B0.9600
C6—O1—C2113.1 (3)C14—C13—C16129.1 (3)
C8—N4—C5121.9 (3)C15—C14—C13107.3 (3)
C8—N4—C3126.2 (3)C15—C14—H14126.3
C5—N4—C3111.7 (3)C13—C14—H14126.3
C15—N11—N12112.4 (3)N11—C15—C14105.3 (3)
C15—N11—C8128.9 (3)N11—C15—C17123.0 (3)
N12—N11—C8118.1 (3)C14—C15—C17131.7 (3)
C13—N12—N11104.0 (3)C13—C16—H16A109.5
O1—C2—C3111.3 (4)C13—C16—H16B109.5
O1—C2—C7108.5 (3)H16A—C16—H16B109.5
C3—C2—C7112.3 (4)C13—C16—H16C109.5
O1—C2—H2108.2H16A—C16—H16C109.5
C3—C2—H2108.2H16B—C16—H16C109.5
C7—C2—H2108.2C13—C16—H16D109.5
C2—C3—N4111.8 (3)H16A—C16—H16D141.1
C2—C3—H3A109.3H16B—C16—H16D56.3
N4—C3—H3A109.3H16C—C16—H16D56.3
C2—C3—H3B109.3C13—C16—H16E109.5
N4—C3—H3B109.3H16A—C16—H16E56.3
H3A—C3—H3B107.9H16B—C16—H16E141.1
C6—C5—N4111.0 (4)H16C—C16—H16E56.3
C6—C5—H5A109.4H16D—C16—H16E109.5
N4—C5—H5A109.4C13—C16—H16F109.5
C6—C5—H5B109.4H16A—C16—H16F56.3
N4—C5—H5B109.4H16B—C16—H16F56.3
H5A—C5—H5B108.0H16C—C16—H16F141.1
O1—C6—C5112.2 (4)H16D—C16—H16F109.5
O1—C6—C10108.3 (4)H16E—C16—H16F109.5
C5—C6—C10113.9 (5)C15—C17—H17A109.5
O1—C6—H6107.4C15—C17—H17B109.5
C5—C6—H6107.4H17A—C17—H17B109.5
C10—C6—H6107.4C15—C17—H17C109.5
C2—C7—H7A109.5H17A—C17—H17C109.5
C2—C7—H7B109.5H17B—C17—H17C109.5
H7A—C7—H7B109.5C15—C17—H17D109.5
C2—C7—H7C109.5H17A—C17—H17D141.1
H7A—C7—H7C109.5H17B—C17—H17D56.3
H7B—C7—H7C109.5H17C—C17—H17D56.3
N4—C8—N11114.1 (3)C15—C17—H17E109.5
N4—C8—S9126.8 (3)H17A—C17—H17E56.3
N11—C8—S9119.0 (3)H17B—C17—H17E141.1
C6—C10—H10A109.5H17C—C17—H17E56.3
C6—C10—H10B109.5H17D—C17—H17E109.5
H10A—C10—H10B109.5C15—C17—H17F109.5
C6—C10—H10C109.5H17A—C17—H17F56.3
H10A—C10—H10C109.5H17B—C17—H17F56.3
H10B—C10—H10C109.5H17C—C17—H17F141.1
N12—C13—C14111.0 (3)H17D—C17—H17F109.5
N12—C13—C16119.9 (4)H17E—C17—H17F109.5
C15—N11—N12—C130.0 (4)C5—N4—C8—S97.3 (6)
C8—N11—N12—C13171.9 (3)C3—N4—C8—S9178.5 (4)
C6—O1—C2—C355.3 (5)C15—N11—C8—N4122.8 (4)
C6—O1—C2—C7179.4 (4)N12—N11—C8—N466.8 (4)
O1—C2—C3—N451.7 (5)C15—N11—C8—S960.4 (5)
C7—C2—C3—N4173.5 (4)N12—N11—C8—S9110.1 (3)
C8—N4—C3—C2134.8 (4)N11—N12—C13—C140.4 (4)
C5—N4—C3—C250.6 (5)N11—N12—C13—C16179.0 (3)
C8—N4—C5—C6133.4 (5)N12—C13—C14—C150.6 (4)
C3—N4—C5—C651.7 (6)C16—C13—C14—C15178.7 (4)
C2—O1—C6—C557.5 (5)N12—N11—C15—C140.3 (4)
C2—O1—C6—C10175.9 (4)C8—N11—C15—C14171.2 (3)
N4—C5—C6—O154.9 (6)N12—N11—C15—C17178.8 (3)
N4—C5—C6—C10178.4 (4)C8—N11—C15—C1710.3 (6)
C5—N4—C8—N11169.2 (4)C13—C14—C15—N110.5 (4)
C3—N4—C8—N114.9 (6)C13—C14—C15—C17178.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···N110.972.372.780 (5)105
C3—H3A···N120.972.573.013 (5)108
C5—H5B···S90.972.593.087 (5)112
C2—H2···N12i0.982.743.560 (6)142
Symmetry code: (i) x1, y, z.
 

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