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organic compounds
The title compound, C14H17N3OS, exists in the E,E configuration with respect to the C=N bonds of the thiadiazole ring. In the crystal packing, molecules are linked into centrosymmetric dimers through N—HN hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046988/bh2055sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046988/bh2055Isup2.hkl |
CCDC reference: 629428
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.112
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
2-[5-(Cyclohexylamino)-1,3,4-thiadiazol-2-yl]phenol top
Crystal data top
C14H17N3OS | F(000) = 584 |
Mr = 275.37 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6819 reflections |
a = 7.9402 (16) Å | θ = 3.1–32.2° |
b = 10.5702 (10) Å | µ = 0.23 mm−1 |
c = 16.545 (6) Å | T = 293 K |
β = 95.65 (2)° | Block, intense gold |
V = 1381.9 (6) Å3 | 0.33 × 0.26 × 0.21 mm |
Z = 4 |
Data collection top
Oxford Diffraction Xcalibur-S diffractometer | 3173 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2483 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 15.9948 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −13→13 |
Tmin = 0.928, Tmax = 0.962 | l = −21→21 |
16447 measured reflections |
Refinement top
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0601P)2 + 0.2525P] where P = (Fo2 + 2Fc2)/3 |
3173 reflections | (Δ/σ)max < 0.001 |
180 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.3261 (2) | 0.35076 (17) | 0.99082 (11) | 0.0442 (4) | |
C2 | 0.3693 (2) | 0.14868 (17) | 1.05501 (10) | 0.0399 (4) | |
C3 | 0.3701 (2) | 0.01833 (16) | 1.08459 (11) | 0.0410 (4) | |
C4 | 0.4751 (2) | −0.01582 (18) | 1.15407 (12) | 0.0470 (4) | |
C5 | 0.4726 (3) | −0.13888 (19) | 1.18317 (13) | 0.0572 (5) | |
H5 | 0.5404 | −0.1608 | 1.2301 | 0.069* | |
C6 | 0.3708 (3) | −0.22840 (19) | 1.14326 (14) | 0.0596 (5) | |
H6 | 0.3709 | −0.3108 | 1.1629 | 0.071* | |
C7 | 0.2686 (3) | −0.19674 (19) | 1.07426 (14) | 0.0605 (5) | |
H7 | 0.2003 | −0.2578 | 1.0470 | 0.073* | |
C8 | 0.2676 (3) | −0.07452 (19) | 1.04560 (12) | 0.0533 (5) | |
H8 | 0.1971 | −0.0535 | 0.9993 | 0.064* | |
C9 | 0.1350 (2) | 0.45879 (17) | 0.88503 (11) | 0.0453 (4) | |
H9 | 0.0519 | 0.3951 | 0.8977 | 0.054* | |
C10 | 0.1877 (3) | 0.4296 (2) | 0.80201 (13) | 0.0590 (5) | |
H10A | 0.2312 | 0.3438 | 0.8014 | 0.071* | |
H10B | 0.2778 | 0.4866 | 0.7903 | 0.071* | |
C11 | 0.0397 (3) | 0.4432 (2) | 0.73650 (13) | 0.0630 (6) | |
H11A | 0.0792 | 0.4294 | 0.6835 | 0.076* | |
H11B | −0.0449 | 0.3794 | 0.7445 | 0.076* | |
C12 | −0.0395 (3) | 0.5734 (2) | 0.73904 (13) | 0.0591 (5) | |
H12A | 0.0420 | 0.6368 | 0.7261 | 0.071* | |
H12B | −0.1363 | 0.5785 | 0.6986 | 0.071* | |
C13 | −0.0950 (2) | 0.5997 (2) | 0.82148 (13) | 0.0566 (5) | |
H13A | −0.1838 | 0.5408 | 0.8323 | 0.068* | |
H13B | −0.1409 | 0.6847 | 0.8225 | 0.068* | |
C14 | 0.0523 (3) | 0.58696 (19) | 0.88719 (12) | 0.0548 (5) | |
H14A | 0.1354 | 0.6520 | 0.8797 | 0.066* | |
H14B | 0.0116 | 0.5997 | 0.9400 | 0.066* | |
N1 | 0.2764 (2) | 0.45366 (16) | 0.94827 (11) | 0.0581 (5) | |
N2 | 0.45465 (18) | 0.35072 (14) | 1.04720 (10) | 0.0476 (4) | |
N3 | 0.47644 (19) | 0.23403 (14) | 1.08354 (10) | 0.0465 (4) | |
O1 | 0.5802 (2) | 0.06802 (15) | 1.19519 (10) | 0.0688 (5) | |
S1 | 0.22390 (6) | 0.20511 (4) | 0.97814 (3) | 0.04692 (15) | |
H1N | 0.348 (3) | 0.513 (2) | 0.9501 (13) | 0.059 (6)* | |
H101 | 0.571 (4) | 0.138 (3) | 1.1689 (18) | 0.104 (10)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0398 (9) | 0.0433 (9) | 0.0484 (10) | −0.0070 (7) | −0.0012 (7) | 0.0000 (8) |
C2 | 0.0367 (8) | 0.0423 (9) | 0.0404 (9) | 0.0002 (7) | 0.0017 (7) | −0.0015 (7) |
C3 | 0.0396 (9) | 0.0392 (9) | 0.0448 (9) | 0.0017 (7) | 0.0070 (7) | −0.0021 (7) |
C4 | 0.0421 (9) | 0.0446 (10) | 0.0535 (11) | 0.0031 (8) | 0.0011 (8) | −0.0022 (8) |
C5 | 0.0533 (11) | 0.0511 (12) | 0.0661 (13) | 0.0091 (9) | 0.0000 (10) | 0.0114 (10) |
C6 | 0.0615 (13) | 0.0405 (11) | 0.0784 (14) | 0.0021 (9) | 0.0154 (11) | 0.0084 (10) |
C7 | 0.0653 (13) | 0.0461 (11) | 0.0704 (14) | −0.0140 (10) | 0.0084 (11) | −0.0046 (10) |
C8 | 0.0560 (11) | 0.0508 (11) | 0.0516 (11) | −0.0082 (9) | −0.0020 (9) | −0.0007 (9) |
C9 | 0.0392 (9) | 0.0421 (9) | 0.0527 (10) | −0.0086 (7) | −0.0046 (8) | 0.0096 (8) |
C10 | 0.0530 (11) | 0.0572 (12) | 0.0674 (13) | 0.0082 (9) | 0.0083 (10) | 0.0020 (10) |
C11 | 0.0692 (14) | 0.0704 (14) | 0.0488 (11) | 0.0059 (11) | 0.0026 (10) | −0.0015 (10) |
C12 | 0.0582 (12) | 0.0601 (13) | 0.0568 (12) | −0.0004 (10) | −0.0053 (9) | 0.0151 (10) |
C13 | 0.0490 (11) | 0.0545 (11) | 0.0643 (13) | 0.0085 (9) | −0.0036 (9) | 0.0036 (10) |
C14 | 0.0546 (11) | 0.0536 (11) | 0.0544 (11) | 0.0020 (9) | −0.0027 (9) | −0.0034 (9) |
N1 | 0.0489 (9) | 0.0467 (9) | 0.0736 (12) | −0.0152 (8) | −0.0191 (8) | 0.0169 (8) |
N2 | 0.0432 (8) | 0.0409 (8) | 0.0560 (9) | −0.0060 (7) | −0.0092 (7) | 0.0041 (7) |
N3 | 0.0440 (8) | 0.0411 (8) | 0.0522 (9) | −0.0029 (6) | −0.0060 (7) | 0.0021 (7) |
O1 | 0.0713 (10) | 0.0515 (9) | 0.0763 (11) | −0.0037 (7) | −0.0300 (8) | 0.0072 (8) |
S1 | 0.0454 (3) | 0.0443 (3) | 0.0483 (3) | −0.0091 (2) | −0.00922 (18) | 0.0029 (2) |
Geometric parameters (Å, º) top
C1—N2 | 1.313 (2) | C9—C10 | 1.507 (3) |
C1—N1 | 1.334 (2) | C9—H9 | 0.9800 |
C1—S1 | 1.7432 (18) | C10—C11 | 1.525 (3) |
C2—N3 | 1.297 (2) | C10—H10A | 0.9700 |
C2—C3 | 1.462 (2) | C10—H10B | 0.9700 |
C2—S1 | 1.7369 (18) | C11—C12 | 1.516 (3) |
C3—C8 | 1.392 (3) | C11—H11A | 0.9700 |
C3—C4 | 1.400 (3) | C11—H11B | 0.9700 |
C4—O1 | 1.354 (2) | C12—C13 | 1.500 (3) |
C4—C5 | 1.388 (3) | C12—H12A | 0.9700 |
C5—C6 | 1.371 (3) | C12—H12B | 0.9700 |
C5—H5 | 0.9300 | C13—C14 | 1.522 (3) |
C6—C7 | 1.375 (3) | C13—H13A | 0.9700 |
C6—H6 | 0.9300 | C13—H13B | 0.9700 |
C7—C8 | 1.376 (3) | C14—H14A | 0.9700 |
C7—H7 | 0.9300 | C14—H14B | 0.9700 |
C8—H8 | 0.9300 | N1—H1N | 0.85 (2) |
C9—N1 | 1.458 (2) | N2—N3 | 1.376 (2) |
C9—C14 | 1.508 (3) | O1—H101 | 0.86 (3) |
N2—C1—N1 | 122.95 (16) | C11—C10—H10B | 109.3 |
N2—C1—S1 | 113.91 (13) | H10A—C10—H10B | 108.0 |
N1—C1—S1 | 123.13 (14) | C12—C11—C10 | 111.02 (18) |
N3—C2—C3 | 123.56 (16) | C12—C11—H11A | 109.4 |
N3—C2—S1 | 113.12 (13) | C10—C11—H11A | 109.4 |
C3—C2—S1 | 123.33 (13) | C12—C11—H11B | 109.4 |
C8—C3—C4 | 118.21 (17) | C10—C11—H11B | 109.4 |
C8—C3—C2 | 121.75 (16) | H11A—C11—H11B | 108.0 |
C4—C3—C2 | 120.04 (16) | C13—C12—C11 | 110.68 (17) |
O1—C4—C5 | 117.94 (18) | C13—C12—H12A | 109.5 |
O1—C4—C3 | 122.14 (17) | C11—C12—H12A | 109.5 |
C5—C4—C3 | 119.91 (18) | C13—C12—H12B | 109.5 |
C6—C5—C4 | 120.53 (19) | C11—C12—H12B | 109.5 |
C6—C5—H5 | 119.7 | H12A—C12—H12B | 108.1 |
C4—C5—H5 | 119.7 | C12—C13—C14 | 111.06 (16) |
C5—C6—C7 | 120.24 (19) | C12—C13—H13A | 109.4 |
C5—C6—H6 | 119.9 | C14—C13—H13A | 109.4 |
C7—C6—H6 | 119.9 | C12—C13—H13B | 109.4 |
C6—C7—C8 | 119.83 (19) | C14—C13—H13B | 109.4 |
C6—C7—H7 | 120.1 | H13A—C13—H13B | 108.0 |
C8—C7—H7 | 120.1 | C9—C14—C13 | 111.63 (16) |
C7—C8—C3 | 121.25 (19) | C9—C14—H14A | 109.3 |
C7—C8—H8 | 119.4 | C13—C14—H14A | 109.3 |
C3—C8—H8 | 119.4 | C9—C14—H14B | 109.3 |
N1—C9—C14 | 108.84 (16) | C13—C14—H14B | 109.3 |
N1—C9—C10 | 112.56 (16) | H14A—C14—H14B | 108.0 |
C14—C9—C10 | 111.51 (16) | C1—N1—C9 | 125.16 (16) |
N1—C9—H9 | 107.9 | C1—N1—H1N | 115.1 (15) |
C14—C9—H9 | 107.9 | C9—N1—H1N | 117.7 (15) |
C10—C9—H9 | 107.9 | C1—N2—N3 | 111.48 (14) |
C9—C10—C11 | 111.41 (16) | C2—N3—N2 | 114.51 (15) |
C9—C10—H10A | 109.3 | C4—O1—H101 | 107 (2) |
C11—C10—H10A | 109.3 | C2—S1—C1 | 86.98 (9) |
C9—C10—H10B | 109.3 | ||
N3—C2—C3—C8 | −171.52 (18) | C10—C11—C12—C13 | −56.6 (2) |
S1—C2—C3—C8 | 8.7 (3) | C11—C12—C13—C14 | 56.7 (2) |
N3—C2—C3—C4 | 8.8 (3) | N1—C9—C14—C13 | 178.99 (16) |
S1—C2—C3—C4 | −170.99 (14) | C10—C9—C14—C13 | 54.2 (2) |
C8—C3—C4—O1 | 179.22 (18) | C12—C13—C14—C9 | −55.8 (2) |
C2—C3—C4—O1 | −1.1 (3) | N2—C1—N1—C9 | 179.85 (18) |
C8—C3—C4—C5 | −1.3 (3) | S1—C1—N1—C9 | −1.5 (3) |
C2—C3—C4—C5 | 178.41 (18) | C14—C9—N1—C1 | 146.0 (2) |
O1—C4—C5—C6 | −178.87 (19) | C10—C9—N1—C1 | −89.9 (2) |
C3—C4—C5—C6 | 1.6 (3) | N1—C1—N2—N3 | 178.19 (18) |
C4—C5—C6—C7 | −0.7 (3) | S1—C1—N2—N3 | −0.6 (2) |
C5—C6—C7—C8 | −0.5 (3) | C3—C2—N3—N2 | 179.73 (16) |
C6—C7—C8—C3 | 0.8 (3) | S1—C2—N3—N2 | −0.5 (2) |
C4—C3—C8—C7 | 0.1 (3) | C1—N2—N3—C2 | 0.7 (2) |
C2—C3—C8—C7 | −179.61 (19) | N3—C2—S1—C1 | 0.12 (14) |
N1—C9—C10—C11 | −176.67 (17) | C3—C2—S1—C1 | 179.91 (16) |
C14—C9—C10—C11 | −54.0 (2) | N2—C1—S1—C2 | 0.28 (15) |
C9—C10—C11—C12 | 55.2 (2) | N1—C1—S1—C2 | −178.49 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H101···N3 | 0.86 (3) | 1.84 (3) | 2.621 (2) | 151 (3) |
N1—H1N···N2i | 0.85 (2) | 2.13 (2) | 2.968 (2) | 175 (2) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
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