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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—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046988/bh2055sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046988/bh2055Isup2.hkl
Contains datablock I

CCDC reference: 629428

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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
C14H17N3OSF(000) = 584
Mr = 275.37Dx = 1.324 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6819 reflections
a = 7.9402 (16) Åθ = 3.1–32.2°
b = 10.5702 (10) ŵ = 0.23 mm1
c = 16.545 (6) ÅT = 293 K
β = 95.65 (2)°Block, intense gold
V = 1381.9 (6) Å30.33 × 0.26 × 0.21 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur-S
diffractometer
3173 independent reflections
Radiation source: Enhance (Mo) X-ray Source2483 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 15.9948 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1010
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)
k = 1313
Tmin = 0.928, Tmax = 0.962l = 2121
16447 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H 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 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.19 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3261 (2)0.35076 (17)0.99082 (11)0.0442 (4)
C20.3693 (2)0.14868 (17)1.05501 (10)0.0399 (4)
C30.3701 (2)0.01833 (16)1.08459 (11)0.0410 (4)
C40.4751 (2)0.01582 (18)1.15407 (12)0.0470 (4)
C50.4726 (3)0.13888 (19)1.18317 (13)0.0572 (5)
H50.54040.16081.23010.069*
C60.3708 (3)0.22840 (19)1.14326 (14)0.0596 (5)
H60.37090.31081.16290.071*
C70.2686 (3)0.19674 (19)1.07426 (14)0.0605 (5)
H70.20030.25781.04700.073*
C80.2676 (3)0.07452 (19)1.04560 (12)0.0533 (5)
H80.19710.05350.99930.064*
C90.1350 (2)0.45879 (17)0.88503 (11)0.0453 (4)
H90.05190.39510.89770.054*
C100.1877 (3)0.4296 (2)0.80201 (13)0.0590 (5)
H10A0.23120.34380.80140.071*
H10B0.27780.48660.79030.071*
C110.0397 (3)0.4432 (2)0.73650 (13)0.0630 (6)
H11A0.07920.42940.68350.076*
H11B0.04490.37940.74450.076*
C120.0395 (3)0.5734 (2)0.73904 (13)0.0591 (5)
H12A0.04200.63680.72610.071*
H12B0.13630.57850.69860.071*
C130.0950 (2)0.5997 (2)0.82148 (13)0.0566 (5)
H13A0.18380.54080.83230.068*
H13B0.14090.68470.82250.068*
C140.0523 (3)0.58696 (19)0.88719 (12)0.0548 (5)
H14A0.13540.65200.87970.066*
H14B0.01160.59970.94000.066*
N10.2764 (2)0.45366 (16)0.94827 (11)0.0581 (5)
N20.45465 (18)0.35072 (14)1.04720 (10)0.0476 (4)
N30.47644 (19)0.23403 (14)1.08354 (10)0.0465 (4)
O10.5802 (2)0.06802 (15)1.19519 (10)0.0688 (5)
S10.22390 (6)0.20511 (4)0.97814 (3)0.04692 (15)
H1N0.348 (3)0.513 (2)0.9501 (13)0.059 (6)*
H1010.571 (4)0.138 (3)1.1689 (18)0.104 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0398 (9)0.0433 (9)0.0484 (10)0.0070 (7)0.0012 (7)0.0000 (8)
C20.0367 (8)0.0423 (9)0.0404 (9)0.0002 (7)0.0017 (7)0.0015 (7)
C30.0396 (9)0.0392 (9)0.0448 (9)0.0017 (7)0.0070 (7)0.0021 (7)
C40.0421 (9)0.0446 (10)0.0535 (11)0.0031 (8)0.0011 (8)0.0022 (8)
C50.0533 (11)0.0511 (12)0.0661 (13)0.0091 (9)0.0000 (10)0.0114 (10)
C60.0615 (13)0.0405 (11)0.0784 (14)0.0021 (9)0.0154 (11)0.0084 (10)
C70.0653 (13)0.0461 (11)0.0704 (14)0.0140 (10)0.0084 (11)0.0046 (10)
C80.0560 (11)0.0508 (11)0.0516 (11)0.0082 (9)0.0020 (9)0.0007 (9)
C90.0392 (9)0.0421 (9)0.0527 (10)0.0086 (7)0.0046 (8)0.0096 (8)
C100.0530 (11)0.0572 (12)0.0674 (13)0.0082 (9)0.0083 (10)0.0020 (10)
C110.0692 (14)0.0704 (14)0.0488 (11)0.0059 (11)0.0026 (10)0.0015 (10)
C120.0582 (12)0.0601 (13)0.0568 (12)0.0004 (10)0.0053 (9)0.0151 (10)
C130.0490 (11)0.0545 (11)0.0643 (13)0.0085 (9)0.0036 (9)0.0036 (10)
C140.0546 (11)0.0536 (11)0.0544 (11)0.0020 (9)0.0027 (9)0.0034 (9)
N10.0489 (9)0.0467 (9)0.0736 (12)0.0152 (8)0.0191 (8)0.0169 (8)
N20.0432 (8)0.0409 (8)0.0560 (9)0.0060 (7)0.0092 (7)0.0041 (7)
N30.0440 (8)0.0411 (8)0.0522 (9)0.0029 (6)0.0060 (7)0.0021 (7)
O10.0713 (10)0.0515 (9)0.0763 (11)0.0037 (7)0.0300 (8)0.0072 (8)
S10.0454 (3)0.0443 (3)0.0483 (3)0.0091 (2)0.00922 (18)0.0029 (2)
Geometric parameters (Å, º) top
C1—N21.313 (2)C9—C101.507 (3)
C1—N11.334 (2)C9—H90.9800
C1—S11.7432 (18)C10—C111.525 (3)
C2—N31.297 (2)C10—H10A0.9700
C2—C31.462 (2)C10—H10B0.9700
C2—S11.7369 (18)C11—C121.516 (3)
C3—C81.392 (3)C11—H11A0.9700
C3—C41.400 (3)C11—H11B0.9700
C4—O11.354 (2)C12—C131.500 (3)
C4—C51.388 (3)C12—H12A0.9700
C5—C61.371 (3)C12—H12B0.9700
C5—H50.9300C13—C141.522 (3)
C6—C71.375 (3)C13—H13A0.9700
C6—H60.9300C13—H13B0.9700
C7—C81.376 (3)C14—H14A0.9700
C7—H70.9300C14—H14B0.9700
C8—H80.9300N1—H1N0.85 (2)
C9—N11.458 (2)N2—N31.376 (2)
C9—C141.508 (3)O1—H1010.86 (3)
N2—C1—N1122.95 (16)C11—C10—H10B109.3
N2—C1—S1113.91 (13)H10A—C10—H10B108.0
N1—C1—S1123.13 (14)C12—C11—C10111.02 (18)
N3—C2—C3123.56 (16)C12—C11—H11A109.4
N3—C2—S1113.12 (13)C10—C11—H11A109.4
C3—C2—S1123.33 (13)C12—C11—H11B109.4
C8—C3—C4118.21 (17)C10—C11—H11B109.4
C8—C3—C2121.75 (16)H11A—C11—H11B108.0
C4—C3—C2120.04 (16)C13—C12—C11110.68 (17)
O1—C4—C5117.94 (18)C13—C12—H12A109.5
O1—C4—C3122.14 (17)C11—C12—H12A109.5
C5—C4—C3119.91 (18)C13—C12—H12B109.5
C6—C5—C4120.53 (19)C11—C12—H12B109.5
C6—C5—H5119.7H12A—C12—H12B108.1
C4—C5—H5119.7C12—C13—C14111.06 (16)
C5—C6—C7120.24 (19)C12—C13—H13A109.4
C5—C6—H6119.9C14—C13—H13A109.4
C7—C6—H6119.9C12—C13—H13B109.4
C6—C7—C8119.83 (19)C14—C13—H13B109.4
C6—C7—H7120.1H13A—C13—H13B108.0
C8—C7—H7120.1C9—C14—C13111.63 (16)
C7—C8—C3121.25 (19)C9—C14—H14A109.3
C7—C8—H8119.4C13—C14—H14A109.3
C3—C8—H8119.4C9—C14—H14B109.3
N1—C9—C14108.84 (16)C13—C14—H14B109.3
N1—C9—C10112.56 (16)H14A—C14—H14B108.0
C14—C9—C10111.51 (16)C1—N1—C9125.16 (16)
N1—C9—H9107.9C1—N1—H1N115.1 (15)
C14—C9—H9107.9C9—N1—H1N117.7 (15)
C10—C9—H9107.9C1—N2—N3111.48 (14)
C9—C10—C11111.41 (16)C2—N3—N2114.51 (15)
C9—C10—H10A109.3C4—O1—H101107 (2)
C11—C10—H10A109.3C2—S1—C186.98 (9)
C9—C10—H10B109.3
N3—C2—C3—C8171.52 (18)C10—C11—C12—C1356.6 (2)
S1—C2—C3—C88.7 (3)C11—C12—C13—C1456.7 (2)
N3—C2—C3—C48.8 (3)N1—C9—C14—C13178.99 (16)
S1—C2—C3—C4170.99 (14)C10—C9—C14—C1354.2 (2)
C8—C3—C4—O1179.22 (18)C12—C13—C14—C955.8 (2)
C2—C3—C4—O11.1 (3)N2—C1—N1—C9179.85 (18)
C8—C3—C4—C51.3 (3)S1—C1—N1—C91.5 (3)
C2—C3—C4—C5178.41 (18)C14—C9—N1—C1146.0 (2)
O1—C4—C5—C6178.87 (19)C10—C9—N1—C189.9 (2)
C3—C4—C5—C61.6 (3)N1—C1—N2—N3178.19 (18)
C4—C5—C6—C70.7 (3)S1—C1—N2—N30.6 (2)
C5—C6—C7—C80.5 (3)C3—C2—N3—N2179.73 (16)
C6—C7—C8—C30.8 (3)S1—C2—N3—N20.5 (2)
C4—C3—C8—C70.1 (3)C1—N2—N3—C20.7 (2)
C2—C3—C8—C7179.61 (19)N3—C2—S1—C10.12 (14)
N1—C9—C10—C11176.67 (17)C3—C2—S1—C1179.91 (16)
C14—C9—C10—C1154.0 (2)N2—C1—S1—C20.28 (15)
C9—C10—C11—C1255.2 (2)N1—C1—S1—C2178.49 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H101···N30.86 (3)1.84 (3)2.621 (2)151 (3)
N1—H1N···N2i0.85 (2)2.13 (2)2.968 (2)175 (2)
Symmetry code: (i) x+1, y+1, z+2.
 

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