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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
CCDC reference: 618193
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (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
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-1
H-pyrazole thioketone
top
Crystal data top
C12H19N3OS | Z = 2 |
Mr = 253.37 | F(000) = 272 |
Triclinic, P1 | Dx = 1.215 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 5.242 (2) Å | Cell parameters from 25 reflections |
b = 11.209 (2) Å | θ = 13.1–43.8° |
c = 12.082 (2) Å | µ = 1.99 mm−1 |
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 tube | Rint = 0.016 |
Graphite monochromator | θmax = 67.9°, θmin = 3.7° |
non–profiled ω/2θ scans | h = −6→6 |
Absorption correction: ψ scan (North et al., 1968) | k = −13→13 |
Tmin = 0.587, Tmax = 0.857 | l = −1→14 |
2875 measured reflections | 2 standard reflections every 120 min |
2507 independent reflections | intensity decay: 3% |
Refinement top
Refinement on F2 | H-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) = 0.248 | Δρmax = 0.72 e Å−3 |
S = 1.04 | Δρmin = −0.35 e Å−3 |
2507 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
155 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
S9 | 1.0113 (4) | 0.79575 (11) | 0.53249 (10) | 0.1128 (7) | |
O1 | 0.3537 (5) | 0.9903 (2) | 0.8427 (2) | 0.0681 (8) | |
N4 | 0.7476 (7) | 0.8366 (3) | 0.7328 (3) | 0.0722 (10) | |
N11 | 0.9181 (6) | 0.6407 (2) | 0.7125 (2) | 0.0548 (7) | |
N12 | 1.0743 (6) | 0.6174 (3) | 0.7959 (2) | 0.0601 (8) | |
C2 | 0.3596 (9) | 0.8630 (4) | 0.8736 (4) | 0.0767 (12) | |
H2 | 0.2504 | 0.8296 | 0.8285 | 0.092* | |
C3 | 0.6247 (9) | 0.8038 (4) | 0.8501 (4) | 0.0795 (12) | |
H3A | 0.6191 | 0.7170 | 0.8628 | 0.095* | |
H3B | 0.7293 | 0.8271 | 0.9019 | 0.095* | |
C5 | 0.7272 (10) | 0.9686 (4) | 0.7033 (4) | 0.0882 (14) | |
H5A | 0.8363 | 1.0049 | 0.7451 | 0.106* | |
H5B | 0.7889 | 0.9864 | 0.6236 | 0.106* | |
C6 | 0.4612 (10) | 1.0203 (4) | 0.7291 (4) | 0.0855 (14) | |
H6 | 0.3586 | 0.9859 | 0.6819 | 0.103* | |
C7 | 0.2456 (9) | 0.8420 (4) | 0.9941 (4) | 0.0775 (12) | |
H7A | 0.0732 | 0.8820 | 1.0055 | 0.116* | |
H7B | 0.3511 | 0.8733 | 1.0398 | 0.116* | |
H7C | 0.2386 | 0.7569 | 1.0149 | 0.116* | |
C8 | 0.8801 (7) | 0.7615 (3) | 0.6630 (3) | 0.0591 (9) | |
C10 | 0.4272 (12) | 1.1545 (4) | 0.7041 (5) | 0.0999 (17) | |
H10A | 0.2473 | 1.1826 | 0.7230 | 0.150* | |
H10B | 0.4839 | 1.1761 | 0.6254 | 0.150* | |
H10C | 0.5285 | 1.1910 | 0.7480 | 0.150* | |
C13 | 1.1001 (7) | 0.4983 (3) | 0.8138 (3) | 0.0577 (9) | |
C14 | 0.9634 (7) | 0.4467 (3) | 0.7445 (3) | 0.0628 (9) | |
H14 | 0.9521 | 0.3648 | 0.7428 | 0.075* | |
C15 | 0.8498 (7) | 0.5383 (3) | 0.6802 (3) | 0.0551 (8) | |
C16 | 1.2626 (9) | 0.4377 (4) | 0.8985 (4) | 0.0791 (12) | |
H16A | 1.3319 | 0.4976 | 0.9327 | 0.119* | 0.50 |
H16B | 1.4027 | 0.3869 | 0.8617 | 0.119* | 0.50 |
H16C | 1.1578 | 0.3897 | 0.9555 | 0.119* | 0.50 |
H16D | 1.2630 | 0.3518 | 0.9006 | 0.119* | 0.50 |
H16E | 1.1922 | 0.4626 | 0.9715 | 0.119* | 0.50 |
H16F | 1.4372 | 0.4598 | 0.8778 | 0.119* | 0.50 |
C17 | 0.6788 (9) | 0.5386 (4) | 0.5933 (4) | 0.0764 (11) | |
H17A | 0.6333 | 0.6203 | 0.5642 | 0.115* | 0.50 |
H17B | 0.5239 | 0.5017 | 0.6266 | 0.115* | 0.50 |
H17C | 0.7687 | 0.4942 | 0.5330 | 0.115* | 0.50 |
H17D | 0.6506 | 0.4572 | 0.5850 | 0.115* | 0.50 |
H17E | 0.7600 | 0.5757 | 0.5226 | 0.115* | 0.50 |
H17F | 0.5152 | 0.5832 | 0.6162 | 0.115* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S9 | 0.1816 (16) | 0.0683 (8) | 0.0662 (8) | 0.0073 (8) | 0.0253 (8) | 0.0066 (5) |
O1 | 0.0775 (17) | 0.0524 (14) | 0.0706 (16) | 0.0091 (11) | −0.0090 (13) | −0.0084 (11) |
N4 | 0.078 (2) | 0.0450 (16) | 0.079 (2) | 0.0109 (14) | 0.0104 (17) | 0.0071 (14) |
N11 | 0.0676 (18) | 0.0441 (14) | 0.0516 (15) | 0.0023 (12) | −0.0114 (13) | −0.0042 (11) |
N12 | 0.0687 (18) | 0.0545 (16) | 0.0583 (17) | 0.0027 (13) | −0.0198 (14) | −0.0042 (13) |
C2 | 0.093 (3) | 0.058 (2) | 0.073 (2) | 0.0017 (19) | −0.002 (2) | −0.0060 (18) |
C3 | 0.086 (3) | 0.064 (2) | 0.076 (3) | 0.008 (2) | 0.004 (2) | 0.0071 (19) |
C5 | 0.098 (3) | 0.051 (2) | 0.100 (3) | 0.007 (2) | 0.008 (3) | 0.010 (2) |
C6 | 0.109 (4) | 0.058 (2) | 0.078 (3) | 0.018 (2) | −0.004 (2) | 0.001 (2) |
C7 | 0.078 (3) | 0.078 (3) | 0.072 (2) | 0.000 (2) | 0.000 (2) | −0.010 (2) |
C8 | 0.068 (2) | 0.0479 (18) | 0.059 (2) | 0.0006 (15) | −0.0116 (16) | 0.0003 (15) |
C10 | 0.124 (4) | 0.057 (2) | 0.103 (4) | 0.028 (2) | −0.003 (3) | 0.004 (2) |
C13 | 0.0591 (19) | 0.0525 (18) | 0.0551 (19) | 0.0071 (15) | −0.0018 (15) | −0.0007 (14) |
C14 | 0.067 (2) | 0.0440 (17) | 0.075 (2) | 0.0011 (15) | −0.0048 (18) | −0.0082 (16) |
C15 | 0.0559 (18) | 0.0518 (18) | 0.0569 (18) | −0.0006 (14) | −0.0047 (15) | −0.0122 (14) |
C16 | 0.077 (3) | 0.081 (3) | 0.073 (3) | 0.019 (2) | −0.017 (2) | 0.004 (2) |
C17 | 0.076 (3) | 0.081 (3) | 0.077 (3) | −0.002 (2) | −0.021 (2) | −0.018 (2) |
Geometric parameters (Å, º) top
S9—C8 | 1.634 (4) | C7—H7C | 0.9600 |
O1—C6 | 1.414 (5) | C10—H10A | 0.9600 |
O1—C2 | 1.430 (5) | C10—H10B | 0.9600 |
N4—C8 | 1.322 (5) | C10—H10C | 0.9600 |
N4—C5 | 1.477 (5) | C13—C14 | 1.396 (5) |
N4—C3 | 1.481 (5) | C13—C16 | 1.493 (5) |
N11—C15 | 1.356 (4) | C14—C15 | 1.357 (5) |
N11—N12 | 1.383 (4) | C14—H14 | 0.9300 |
N11—C8 | 1.422 (4) | C15—C17 | 1.487 (5) |
N12—C13 | 1.322 (4) | C16—H16A | 0.9600 |
C2—C3 | 1.471 (6) | C16—H16B | 0.9600 |
C2—C7 | 1.483 (6) | C16—H16C | 0.9600 |
C2—H2 | 0.9800 | C16—H16D | 0.9600 |
C3—H3A | 0.9700 | C16—H16E | 0.9600 |
C3—H3B | 0.9700 | C16—H16F | 0.9600 |
C5—C6 | 1.449 (6) | C17—H17A | 0.9600 |
C5—H5A | 0.9700 | C17—H17B | 0.9600 |
C5—H5B | 0.9700 | C17—H17C | 0.9600 |
C6—C10 | 1.496 (6) | C17—H17D | 0.9600 |
C6—H6 | 0.9800 | C17—H17E | 0.9600 |
C7—H7A | 0.9600 | C17—H17F | 0.9600 |
C7—H7B | 0.9600 | | |
| | | |
C6—O1—C2 | 113.1 (3) | C14—C13—C16 | 129.1 (3) |
C8—N4—C5 | 121.9 (3) | C15—C14—C13 | 107.3 (3) |
C8—N4—C3 | 126.2 (3) | C15—C14—H14 | 126.3 |
C5—N4—C3 | 111.7 (3) | C13—C14—H14 | 126.3 |
C15—N11—N12 | 112.4 (3) | N11—C15—C14 | 105.3 (3) |
C15—N11—C8 | 128.9 (3) | N11—C15—C17 | 123.0 (3) |
N12—N11—C8 | 118.1 (3) | C14—C15—C17 | 131.7 (3) |
C13—N12—N11 | 104.0 (3) | C13—C16—H16A | 109.5 |
O1—C2—C3 | 111.3 (4) | C13—C16—H16B | 109.5 |
O1—C2—C7 | 108.5 (3) | H16A—C16—H16B | 109.5 |
C3—C2—C7 | 112.3 (4) | C13—C16—H16C | 109.5 |
O1—C2—H2 | 108.2 | H16A—C16—H16C | 109.5 |
C3—C2—H2 | 108.2 | H16B—C16—H16C | 109.5 |
C7—C2—H2 | 108.2 | C13—C16—H16D | 109.5 |
C2—C3—N4 | 111.8 (3) | H16A—C16—H16D | 141.1 |
C2—C3—H3A | 109.3 | H16B—C16—H16D | 56.3 |
N4—C3—H3A | 109.3 | H16C—C16—H16D | 56.3 |
C2—C3—H3B | 109.3 | C13—C16—H16E | 109.5 |
N4—C3—H3B | 109.3 | H16A—C16—H16E | 56.3 |
H3A—C3—H3B | 107.9 | H16B—C16—H16E | 141.1 |
C6—C5—N4 | 111.0 (4) | H16C—C16—H16E | 56.3 |
C6—C5—H5A | 109.4 | H16D—C16—H16E | 109.5 |
N4—C5—H5A | 109.4 | C13—C16—H16F | 109.5 |
C6—C5—H5B | 109.4 | H16A—C16—H16F | 56.3 |
N4—C5—H5B | 109.4 | H16B—C16—H16F | 56.3 |
H5A—C5—H5B | 108.0 | H16C—C16—H16F | 141.1 |
O1—C6—C5 | 112.2 (4) | H16D—C16—H16F | 109.5 |
O1—C6—C10 | 108.3 (4) | H16E—C16—H16F | 109.5 |
C5—C6—C10 | 113.9 (5) | C15—C17—H17A | 109.5 |
O1—C6—H6 | 107.4 | C15—C17—H17B | 109.5 |
C5—C6—H6 | 107.4 | H17A—C17—H17B | 109.5 |
C10—C6—H6 | 107.4 | C15—C17—H17C | 109.5 |
C2—C7—H7A | 109.5 | H17A—C17—H17C | 109.5 |
C2—C7—H7B | 109.5 | H17B—C17—H17C | 109.5 |
H7A—C7—H7B | 109.5 | C15—C17—H17D | 109.5 |
C2—C7—H7C | 109.5 | H17A—C17—H17D | 141.1 |
H7A—C7—H7C | 109.5 | H17B—C17—H17D | 56.3 |
H7B—C7—H7C | 109.5 | H17C—C17—H17D | 56.3 |
N4—C8—N11 | 114.1 (3) | C15—C17—H17E | 109.5 |
N4—C8—S9 | 126.8 (3) | H17A—C17—H17E | 56.3 |
N11—C8—S9 | 119.0 (3) | H17B—C17—H17E | 141.1 |
C6—C10—H10A | 109.5 | H17C—C17—H17E | 56.3 |
C6—C10—H10B | 109.5 | H17D—C17—H17E | 109.5 |
H10A—C10—H10B | 109.5 | C15—C17—H17F | 109.5 |
C6—C10—H10C | 109.5 | H17A—C17—H17F | 56.3 |
H10A—C10—H10C | 109.5 | H17B—C17—H17F | 56.3 |
H10B—C10—H10C | 109.5 | H17C—C17—H17F | 141.1 |
N12—C13—C14 | 111.0 (3) | H17D—C17—H17F | 109.5 |
N12—C13—C16 | 119.9 (4) | H17E—C17—H17F | 109.5 |
| | | |
C15—N11—N12—C13 | 0.0 (4) | C5—N4—C8—S9 | −7.3 (6) |
C8—N11—N12—C13 | −171.9 (3) | C3—N4—C8—S9 | 178.5 (4) |
C6—O1—C2—C3 | 55.3 (5) | C15—N11—C8—N4 | 122.8 (4) |
C6—O1—C2—C7 | 179.4 (4) | N12—N11—C8—N4 | −66.8 (4) |
O1—C2—C3—N4 | −51.7 (5) | C15—N11—C8—S9 | −60.4 (5) |
C7—C2—C3—N4 | −173.5 (4) | N12—N11—C8—S9 | 110.1 (3) |
C8—N4—C3—C2 | −134.8 (4) | N11—N12—C13—C14 | −0.4 (4) |
C5—N4—C3—C2 | 50.6 (5) | N11—N12—C13—C16 | 179.0 (3) |
C8—N4—C5—C6 | 133.4 (5) | N12—C13—C14—C15 | 0.6 (4) |
C3—N4—C5—C6 | −51.7 (6) | C16—C13—C14—C15 | −178.7 (4) |
C2—O1—C6—C5 | −57.5 (5) | N12—N11—C15—C14 | 0.3 (4) |
C2—O1—C6—C10 | 175.9 (4) | C8—N11—C15—C14 | 171.2 (3) |
N4—C5—C6—O1 | 54.9 (6) | N12—N11—C15—C17 | 178.8 (3) |
N4—C5—C6—C10 | 178.4 (4) | C8—N11—C15—C17 | −10.3 (6) |
C5—N4—C8—N11 | 169.2 (4) | C13—C14—C15—N11 | −0.5 (4) |
C3—N4—C8—N11 | −4.9 (6) | C13—C14—C15—C17 | −178.9 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···N11 | 0.97 | 2.37 | 2.780 (5) | 105 |
C3—H3A···N12 | 0.97 | 2.57 | 3.013 (5) | 108 |
C5—H5B···S9 | 0.97 | 2.59 | 3.087 (5) | 112 |
C2—H2···N12i | 0.98 | 2.74 | 3.560 (6) | 142 |
Symmetry code: (i) x−1, y, z. |
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