Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042029/sj6189sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042029/sj6189Isup2.hkl |
CCDC reference: 296671
The title compound was prepared by the method of Wan et al. (2005). Single crystals suitable for an X-ray diffraction study were obtained by slow evaporation of an ethyl acetate–alcohol (1:1 v/v) solution over a period of one week.
All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å and with Uiso(H) = 1.2 or 1.5 Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C16H17FN4O2S2 | Z = 2 |
Mr = 380.46 | F(000) = 396 |
Triclinic, P1 | Dx = 1.437 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7311 (13) Å | Cell parameters from 1446 reflections |
b = 7.7910 (15) Å | θ = 2.3–25.9° |
c = 18.107 (4) Å | µ = 0.33 mm−1 |
α = 98.200 (3)° | T = 293 K |
β = 92.649 (4)° | Plate, colourless |
γ = 109.900 (3)° | 0.29 × 0.21 × 0.09 mm |
V = 879.1 (3) Å3 |
Siemens SMART 1000 CCD area-detector diffractometer | 3385 independent reflections |
Radiation source: fine-focus sealed tube | 2534 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.3° |
ω scans | h = −8→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→9 |
Tmin = 0.910, Tmax = 0.971 | l = −16→22 |
4955 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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0636P)2 + 0.3536P] where P = (Fo2 + 2Fc2)/3 |
3385 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C16H17FN4O2S2 | γ = 109.900 (3)° |
Mr = 380.46 | V = 879.1 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.7311 (13) Å | Mo Kα radiation |
b = 7.7910 (15) Å | µ = 0.33 mm−1 |
c = 18.107 (4) Å | T = 293 K |
α = 98.200 (3)° | 0.29 × 0.21 × 0.09 mm |
β = 92.649 (4)° |
Siemens SMART 1000 CCD area-detector diffractometer | 3385 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2534 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.971 | Rint = 0.014 |
4955 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.33 e Å−3 |
3385 reflections | Δρmin = −0.18 e Å−3 |
226 parameters |
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 | 0.17311 (13) | 0.60830 (11) | 0.24119 (4) | 0.0525 (2) | |
S2 | 0.39342 (16) | 0.41709 (12) | 0.13363 (4) | 0.0658 (3) | |
F1 | 0.6179 (3) | 0.5610 (3) | 0.32055 (10) | 0.0689 (5) | |
O1 | 0.0206 (3) | 0.4158 (4) | 0.39562 (11) | 0.0704 (7) | |
O2 | 0.1976 (4) | 0.9085 (3) | 0.00547 (13) | 0.0714 (7) | |
N1 | 0.2772 (4) | 0.7009 (3) | 0.11157 (12) | 0.0440 (6) | |
N2 | −0.0098 (4) | 0.2475 (3) | 0.25445 (12) | 0.0468 (6) | |
N3 | −0.0062 (4) | 0.0810 (4) | 0.26668 (18) | 0.0681 (8) | |
N4 | −0.3260 (5) | 0.0512 (5) | 0.21260 (18) | 0.0834 (10) | |
C1 | 0.5869 (5) | 0.6355 (4) | 0.38979 (17) | 0.0491 (7) | |
C2 | 0.7643 (5) | 0.7462 (4) | 0.4363 (2) | 0.0616 (9) | |
H2A | 0.8988 | 0.7686 | 0.4203 | 0.074* | |
C3 | 0.7403 (5) | 0.8238 (4) | 0.50711 (19) | 0.0607 (8) | |
H3B | 0.8604 | 0.8978 | 0.5390 | 0.073* | |
C4 | 0.5407 (5) | 0.7942 (4) | 0.53199 (16) | 0.0501 (7) | |
C5 | 0.3666 (5) | 0.6785 (4) | 0.48332 (15) | 0.0454 (7) | |
H5A | 0.2320 | 0.6546 | 0.4994 | 0.054* | |
C6 | 0.3834 (4) | 0.5962 (4) | 0.41141 (15) | 0.0420 (6) | |
C7 | 0.1833 (4) | 0.4699 (4) | 0.36642 (15) | 0.0444 (6) | |
C8 | 0.1770 (4) | 0.4112 (4) | 0.28149 (14) | 0.0424 (6) | |
H8A | 0.3056 | 0.3846 | 0.2702 | 0.051* | |
C9 | 0.2876 (4) | 0.5796 (4) | 0.15465 (14) | 0.0414 (6) | |
C10 | 0.3925 (5) | 0.7235 (5) | 0.04465 (16) | 0.0543 (8) | |
H10A | 0.4244 | 0.6126 | 0.0281 | 0.065* | |
H10B | 0.5260 | 0.8266 | 0.0571 | 0.065* | |
C11 | 0.2647 (6) | 0.7582 (5) | −0.01740 (17) | 0.0650 (9) | |
H11A | 0.3494 | 0.7834 | −0.0591 | 0.078* | |
H11B | 0.1412 | 0.6478 | −0.0346 | 0.078* | |
C12 | 0.0693 (5) | 0.8718 (5) | 0.06493 (19) | 0.0630 (9) | |
H12A | −0.0534 | 0.7603 | 0.0484 | 0.076* | |
H12B | 0.0187 | 0.9735 | 0.0788 | 0.076* | |
C13 | 0.1891 (5) | 0.8476 (4) | 0.13196 (17) | 0.0526 (7) | |
H13A | 0.3034 | 0.9630 | 0.1518 | 0.063* | |
H13B | 0.0948 | 0.8157 | 0.1707 | 0.063* | |
C14 | −0.2013 (6) | 0.2258 (6) | 0.22357 (19) | 0.0699 (10) | |
H14A | −0.2419 | 0.3219 | 0.2113 | 0.084* | |
C15 | −0.1994 (6) | −0.0296 (5) | 0.2400 (2) | 0.0760 (11) | |
H15A | −0.2452 | −0.1564 | 0.2402 | 0.091* | |
C16 | 0.5139 (6) | 0.8809 (5) | 0.60898 (18) | 0.0685 (9) | |
H16A | 0.3656 | 0.8439 | 0.6159 | 0.103* | |
H16B | 0.5732 | 1.0133 | 0.6139 | 0.103* | |
H16C | 0.5860 | 0.8407 | 0.6462 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0777 (6) | 0.0581 (5) | 0.0397 (4) | 0.0414 (4) | 0.0207 (4) | 0.0175 (3) |
S2 | 0.1061 (7) | 0.0742 (6) | 0.0501 (5) | 0.0653 (5) | 0.0306 (4) | 0.0240 (4) |
F1 | 0.0544 (11) | 0.0767 (13) | 0.0656 (12) | 0.0141 (9) | 0.0227 (9) | −0.0027 (10) |
O1 | 0.0449 (12) | 0.1072 (19) | 0.0414 (12) | 0.0070 (12) | 0.0093 (10) | 0.0034 (12) |
O2 | 0.0913 (17) | 0.0882 (16) | 0.0655 (15) | 0.0566 (15) | 0.0233 (13) | 0.0433 (13) |
N1 | 0.0538 (14) | 0.0537 (13) | 0.0369 (12) | 0.0307 (12) | 0.0106 (10) | 0.0151 (10) |
N2 | 0.0467 (14) | 0.0558 (14) | 0.0389 (12) | 0.0200 (12) | 0.0038 (10) | 0.0067 (11) |
N3 | 0.0604 (18) | 0.0506 (15) | 0.092 (2) | 0.0181 (14) | 0.0080 (15) | 0.0122 (15) |
N4 | 0.064 (2) | 0.091 (2) | 0.073 (2) | 0.0088 (19) | −0.0084 (16) | −0.0050 (18) |
C1 | 0.0500 (18) | 0.0456 (15) | 0.0513 (17) | 0.0147 (14) | 0.0103 (14) | 0.0109 (13) |
C2 | 0.0418 (17) | 0.0533 (18) | 0.080 (2) | 0.0038 (15) | 0.0117 (16) | 0.0107 (17) |
C3 | 0.054 (2) | 0.0511 (18) | 0.063 (2) | 0.0029 (15) | −0.0052 (16) | 0.0082 (16) |
C4 | 0.0581 (19) | 0.0458 (15) | 0.0456 (16) | 0.0144 (14) | 0.0021 (14) | 0.0159 (13) |
C5 | 0.0492 (16) | 0.0480 (15) | 0.0426 (15) | 0.0174 (13) | 0.0084 (13) | 0.0175 (13) |
C6 | 0.0449 (16) | 0.0424 (14) | 0.0419 (15) | 0.0158 (12) | 0.0077 (12) | 0.0155 (12) |
C7 | 0.0438 (16) | 0.0530 (16) | 0.0395 (14) | 0.0180 (13) | 0.0090 (12) | 0.0139 (12) |
C8 | 0.0491 (16) | 0.0470 (15) | 0.0370 (14) | 0.0222 (13) | 0.0083 (12) | 0.0117 (12) |
C9 | 0.0484 (16) | 0.0472 (15) | 0.0358 (14) | 0.0244 (13) | 0.0071 (12) | 0.0099 (12) |
C10 | 0.069 (2) | 0.0667 (19) | 0.0454 (16) | 0.0393 (16) | 0.0204 (14) | 0.0228 (14) |
C11 | 0.087 (2) | 0.075 (2) | 0.0453 (17) | 0.039 (2) | 0.0123 (17) | 0.0229 (16) |
C12 | 0.063 (2) | 0.081 (2) | 0.066 (2) | 0.0426 (18) | 0.0148 (16) | 0.0334 (18) |
C13 | 0.067 (2) | 0.0559 (17) | 0.0526 (17) | 0.0393 (16) | 0.0133 (15) | 0.0181 (14) |
C14 | 0.064 (2) | 0.088 (3) | 0.056 (2) | 0.028 (2) | −0.0060 (17) | 0.0069 (18) |
C15 | 0.067 (2) | 0.060 (2) | 0.084 (3) | 0.006 (2) | 0.019 (2) | −0.005 (2) |
C16 | 0.085 (3) | 0.065 (2) | 0.0462 (18) | 0.0162 (19) | −0.0002 (17) | 0.0058 (16) |
S1—C9 | 1.797 (3) | C4—C5 | 1.386 (4) |
S1—C8 | 1.799 (3) | C4—C16 | 1.506 (4) |
S2—C9 | 1.660 (3) | C5—C6 | 1.394 (4) |
F1—C1 | 1.361 (3) | C5—H5A | 0.9300 |
O1—C7 | 1.208 (3) | C6—C7 | 1.488 (4) |
O2—C11 | 1.409 (4) | C7—C8 | 1.535 (4) |
O2—C12 | 1.411 (4) | C8—H8A | 0.9800 |
N1—C9 | 1.326 (3) | C10—C11 | 1.494 (4) |
N1—C13 | 1.468 (3) | C10—H10A | 0.9700 |
N1—C10 | 1.469 (3) | C10—H10B | 0.9700 |
N2—C14 | 1.327 (4) | C11—H11A | 0.9700 |
N2—N3 | 1.355 (3) | C11—H11B | 0.9700 |
N2—C8 | 1.457 (4) | C12—C13 | 1.496 (4) |
N3—C15 | 1.314 (4) | C12—H12A | 0.9700 |
N4—C14 | 1.314 (5) | C12—H12B | 0.9700 |
N4—C15 | 1.336 (5) | C13—H13A | 0.9700 |
C1—C2 | 1.370 (4) | C13—H13B | 0.9700 |
C1—C6 | 1.386 (4) | C14—H14A | 0.9300 |
C2—C3 | 1.379 (5) | C15—H15A | 0.9300 |
C2—H2A | 0.9300 | C16—H16A | 0.9600 |
C3—C4 | 1.391 (4) | C16—H16B | 0.9600 |
C3—H3B | 0.9300 | C16—H16C | 0.9600 |
C9—S1—C8 | 102.84 (12) | N1—C9—S1 | 112.52 (19) |
C11—O2—C12 | 109.9 (2) | S2—C9—S1 | 122.11 (15) |
C9—N1—C13 | 124.7 (2) | N1—C10—C11 | 111.0 (2) |
C9—N1—C10 | 121.5 (2) | N1—C10—H10A | 109.4 |
C13—N1—C10 | 112.7 (2) | C11—C10—H10A | 109.4 |
C14—N2—N3 | 109.1 (3) | N1—C10—H10B | 109.4 |
C14—N2—C8 | 132.4 (3) | C11—C10—H10B | 109.4 |
N3—N2—C8 | 118.3 (2) | H10A—C10—H10B | 108.0 |
C15—N3—N2 | 101.8 (3) | O2—C11—C10 | 112.0 (3) |
C14—N4—C15 | 101.9 (3) | O2—C11—H11A | 109.2 |
F1—C1—C2 | 117.0 (3) | C10—C11—H11A | 109.2 |
F1—C1—C6 | 120.3 (3) | O2—C11—H11B | 109.2 |
C2—C1—C6 | 122.6 (3) | C10—C11—H11B | 109.2 |
C1—C2—C3 | 118.9 (3) | H11A—C11—H11B | 107.9 |
C1—C2—H2A | 120.5 | O2—C12—C13 | 111.5 (2) |
C3—C2—H2A | 120.5 | O2—C12—H12A | 109.3 |
C2—C3—C4 | 121.6 (3) | C13—C12—H12A | 109.3 |
C2—C3—H3B | 119.2 | O2—C12—H12B | 109.3 |
C4—C3—H3B | 119.2 | C13—C12—H12B | 109.3 |
C5—C4—C3 | 117.1 (3) | H12A—C12—H12B | 108.0 |
C5—C4—C16 | 121.1 (3) | N1—C13—C12 | 110.4 (3) |
C3—C4—C16 | 121.7 (3) | N1—C13—H13A | 109.6 |
C4—C5—C6 | 123.2 (3) | C12—C13—H13A | 109.6 |
C4—C5—H5A | 118.4 | N1—C13—H13B | 109.6 |
C6—C5—H5A | 118.4 | C12—C13—H13B | 109.6 |
C1—C6—C5 | 116.5 (3) | H13A—C13—H13B | 108.1 |
C1—C6—C7 | 126.3 (3) | N4—C14—N2 | 111.2 (3) |
C5—C6—C7 | 117.2 (2) | N4—C14—H14A | 124.4 |
O1—C7—C6 | 120.6 (2) | N2—C14—H14A | 124.4 |
O1—C7—C8 | 118.5 (2) | N3—C15—N4 | 115.9 (3) |
C6—C7—C8 | 120.8 (2) | N3—C15—H15A | 122.0 |
N2—C8—C7 | 110.2 (2) | N4—C15—H15A | 122.0 |
N2—C8—S1 | 112.22 (18) | C4—C16—H16A | 109.5 |
C7—C8—S1 | 105.23 (18) | C4—C16—H16B | 109.5 |
N2—C8—H8A | 109.7 | H16A—C16—H16B | 109.5 |
C7—C8—H8A | 109.7 | C4—C16—H16C | 109.5 |
S1—C8—H8A | 109.7 | H16A—C16—H16C | 109.5 |
N1—C9—S2 | 125.4 (2) | H16B—C16—H16C | 109.5 |
C14—N2—N3—C15 | 1.2 (4) | C6—C7—C8—N2 | 162.3 (2) |
C8—N2—N3—C15 | 176.2 (3) | O1—C7—C8—S1 | 101.2 (3) |
F1—C1—C2—C3 | −179.7 (3) | C6—C7—C8—S1 | −76.5 (3) |
C6—C1—C2—C3 | −0.8 (5) | C9—S1—C8—N2 | −85.9 (2) |
C1—C2—C3—C4 | −0.8 (5) | C9—S1—C8—C7 | 154.19 (18) |
C2—C3—C4—C5 | 1.9 (5) | C13—N1—C9—S2 | −178.0 (2) |
C2—C3—C4—C16 | −179.2 (3) | C10—N1—C9—S2 | −10.4 (4) |
C3—C4—C5—C6 | −1.5 (4) | C13—N1—C9—S1 | 1.9 (4) |
C16—C4—C5—C6 | 179.5 (3) | C10—N1—C9—S1 | 169.4 (2) |
F1—C1—C6—C5 | 180.0 (2) | C8—S1—C9—N1 | 172.7 (2) |
C2—C1—C6—C5 | 1.1 (4) | C8—S1—C9—S2 | −7.4 (2) |
F1—C1—C6—C7 | 2.4 (4) | C9—N1—C10—C11 | 142.5 (3) |
C2—C1—C6—C7 | −176.5 (3) | C13—N1—C10—C11 | −48.6 (4) |
C4—C5—C6—C1 | 0.1 (4) | C12—O2—C11—C10 | −60.4 (4) |
C4—C5—C6—C7 | 177.9 (2) | N1—C10—C11—O2 | 53.9 (4) |
C1—C6—C7—O1 | 164.7 (3) | C11—O2—C12—C13 | 61.6 (4) |
C5—C6—C7—O1 | −12.9 (4) | C9—N1—C13—C12 | −142.0 (3) |
C1—C6—C7—C8 | −17.6 (4) | C10—N1—C13—C12 | 49.5 (3) |
C5—C6—C7—C8 | 164.8 (2) | O2—C12—C13—N1 | −56.0 (4) |
C14—N2—C8—C7 | 96.0 (4) | C15—N4—C14—N2 | 1.2 (4) |
N3—N2—C8—C7 | −77.5 (3) | N3—N2—C14—N4 | −1.6 (4) |
C14—N2—C8—S1 | −20.9 (4) | C8—N2—C14—N4 | −175.5 (3) |
N3—N2—C8—S1 | 165.6 (2) | N2—N3—C15—N4 | −0.6 (4) |
O1—C7—C8—N2 | −20.0 (4) | C14—N4—C15—N3 | −0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12B···O2i | 0.97 | 2.53 | 3.207 (4) | 127 |
C13—H13A···N4ii | 0.97 | 2.50 | 3.267 (5) | 135 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H17FN4O2S2 |
Mr | 380.46 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.7311 (13), 7.7910 (15), 18.107 (4) |
α, β, γ (°) | 98.200 (3), 92.649 (4), 109.900 (3) |
V (Å3) | 879.1 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.29 × 0.21 × 0.09 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.910, 0.971 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4955, 3385, 2534 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.138, 1.06 |
No. of reflections | 3385 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.18 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
S1—C9 | 1.797 (3) | F1—C1 | 1.361 (3) |
S1—C8 | 1.799 (3) | O1—C7 | 1.208 (3) |
S2—C9 | 1.660 (3) | ||
N2—C8—C7 | 110.2 (2) | C7—C8—S1 | 105.23 (18) |
N2—C8—S1 | 112.22 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12B···O2i | 0.97 | 2.53 | 3.207 (4) | 127 |
C13—H13A···N4ii | 0.97 | 2.50 | 3.267 (5) | 135 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x+1, y+1, z. |
We have recently reported the structure of 2-(4-chlorophenyl)-2-oxo-1-(1H-1,2,4-triazol-1-ylmethyl)ethyl morpholine-4-carbodithioate, (II) (Wang et al., 2005). As part of our ongoing studies of triazole compounds, the title compound, (I), has been synthesized and its structure is reported here (Fig. 1 and Table 1).
The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987), and are comparable to the corresponding values in (II). The dihedral angle between the C1–C6 and N2–N4/C14/C15 rings is 79.0 (2)°. The morpholine moiety adopts a chair conformation, and atom S2 is synperiplanar with respect to C8, with the C8—S1—C9—S2 torsion angle being −7.4 (2)°. In the crystal structure, molecules are linked into ribbons parallel to the b axis (Fig. 2) by C12—H12B···O2 and C13—H13A···N4 hydrogen bonds (Table 2). π–π stacking interactions involving the C1–C6 benzene rings [Cg···Cg(1 − x, 1 − y, 1 − z) = 3.652 Å] further stabilize the packing, forming two-dimensional layers along the bc plane.