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In the title compound, C14H16N4OS, the dihedral angle between the benzene and triazole rings is 24.0 (2)°. In the crystal structure, mol­ecules are linked into a chain through O—H...S hydrogen bonds. Neighboring chains are further connected by N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041602/is2073sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041602/is2073Isup2.hkl
Contains datablock I

CCDC reference: 627808

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.052
  • wR factor = 0.116
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.23 From the CIF: _reflns_number_total 2585 Count of symmetry unique reflns 1547 Completeness (_total/calc) 167.10% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1038 Fraction of Friedel pairs measured 0.671 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

5-(3-Hydroxypropyl)-4-(3-phenylallylideneamino)-2,4- dihydro-1,2,4-triazole-3-thione top
Crystal data top
C14H16N4OSF(000) = 608
Mr = 288.37Dx = 1.331 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2479 reflections
a = 5.1234 (4) Åθ = 2.9–24.1°
b = 10.5317 (9) ŵ = 0.23 mm1
c = 26.674 (2) ÅT = 298 K
V = 1439.3 (2) Å3Block, colorless
Z = 40.32 × 0.23 × 0.18 mm
Data collection top
Bruker APEX area-detector
diffractometer
2585 independent reflections
Radiation source: fine-focus sealed tube2446 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 66
Tmin = 0.931, Tmax = 0.958k = 1212
7665 measured reflectionsl = 1632
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.052P)2 + 0.2013P]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max = 0.001
2585 reflectionsΔρmax = 0.23 e Å3
182 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: Flack (1983), 1038 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.15 (12)
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.7975 (2)0.63797 (7)0.90517 (3)0.0713 (3)
O10.7438 (4)0.10384 (17)0.96798 (8)0.0615 (6)
H10.77250.17850.96120.092*
N10.4552 (4)0.3405 (2)0.96171 (8)0.0448 (6)
N20.5078 (5)0.4680 (2)0.95623 (8)0.0461 (6)
H20.42730.52600.97290.055*
N30.7675 (4)0.37506 (18)0.90671 (7)0.0401 (5)
N40.9301 (5)0.3365 (2)0.86786 (8)0.0494 (6)
C10.4921 (6)0.0693 (3)0.95000 (12)0.0537 (8)
H1A0.35880.11350.96900.064*
H1B0.47490.09350.91510.064*
C20.4563 (6)0.0714 (3)0.95527 (11)0.0491 (7)
H2A0.48710.09510.98990.059*
H2B0.27690.09270.94720.059*
C30.6376 (5)0.1482 (2)0.92165 (10)0.0463 (6)
H3A0.81650.12210.92770.056*
H3B0.59680.13030.88680.056*
C40.6141 (5)0.2868 (2)0.93066 (9)0.0390 (6)
C50.6921 (6)0.4937 (2)0.92329 (10)0.0452 (6)
C61.1152 (6)0.4094 (3)0.85478 (10)0.0482 (7)
H61.14360.48430.87240.058*
C71.2807 (6)0.3783 (3)0.81345 (10)0.0504 (7)
H71.25740.30070.79740.060*
C81.4665 (6)0.4557 (3)0.79700 (11)0.0522 (7)
H81.49090.52960.81550.063*
C91.6370 (6)0.4401 (3)0.75381 (11)0.0495 (7)
C101.6324 (7)0.3349 (3)0.72307 (12)0.0708 (10)
H101.51820.26880.73030.085*
C111.7921 (8)0.3260 (4)0.68224 (13)0.0844 (12)
H111.78400.25390.66220.101*
C121.9609 (8)0.4191 (4)0.67040 (13)0.0754 (11)
H122.06770.41180.64240.091*
C131.9731 (8)0.5248 (4)0.70032 (14)0.0792 (11)
H132.08810.59020.69250.095*
C141.8151 (7)0.5343 (3)0.74198 (13)0.0661 (9)
H141.82830.60530.76250.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.1042 (7)0.0380 (4)0.0717 (5)0.0034 (4)0.0346 (5)0.0056 (3)
O10.0741 (14)0.0407 (10)0.0697 (14)0.0065 (10)0.0239 (12)0.0149 (10)
N10.0490 (13)0.0433 (13)0.0422 (12)0.0038 (11)0.0070 (11)0.0035 (10)
N20.0544 (14)0.0403 (13)0.0436 (12)0.0073 (11)0.0115 (12)0.0077 (10)
N30.0456 (12)0.0389 (11)0.0358 (11)0.0059 (10)0.0074 (10)0.0024 (9)
N40.0565 (14)0.0450 (13)0.0468 (13)0.0015 (11)0.0151 (11)0.0034 (10)
C10.0551 (19)0.0459 (17)0.0601 (19)0.0070 (14)0.0018 (15)0.0088 (13)
C20.0438 (16)0.0464 (16)0.0570 (17)0.0003 (13)0.0012 (14)0.0050 (13)
C30.0501 (15)0.0456 (15)0.0432 (14)0.0055 (13)0.0043 (13)0.0033 (12)
C40.0406 (14)0.0421 (14)0.0344 (13)0.0044 (12)0.0009 (12)0.0024 (11)
C50.0538 (16)0.0430 (14)0.0388 (13)0.0058 (13)0.0038 (13)0.0056 (11)
C60.0530 (18)0.0505 (16)0.0410 (15)0.0051 (14)0.0018 (14)0.0018 (12)
C70.0554 (18)0.0510 (15)0.0448 (15)0.0000 (15)0.0082 (13)0.0029 (12)
C80.0558 (18)0.0489 (16)0.0520 (17)0.0052 (15)0.0043 (14)0.0002 (13)
C90.0465 (16)0.0541 (17)0.0479 (16)0.0057 (13)0.0043 (14)0.0069 (13)
C100.075 (2)0.065 (2)0.072 (2)0.0139 (19)0.0265 (19)0.0110 (17)
C110.095 (3)0.085 (3)0.073 (2)0.010 (2)0.033 (2)0.0222 (19)
C120.079 (3)0.088 (3)0.060 (2)0.011 (2)0.029 (2)0.0066 (19)
C130.074 (2)0.075 (3)0.088 (3)0.002 (2)0.032 (2)0.020 (2)
C140.069 (2)0.0577 (18)0.072 (2)0.0010 (17)0.0163 (18)0.0040 (16)
Geometric parameters (Å, º) top
S1—C51.684 (3)C3—H3B0.9700
O1—C11.423 (4)C6—C71.429 (4)
O1—H10.8200C6—H60.9300
N1—C41.292 (3)C7—C81.328 (4)
N1—N21.378 (3)C7—H70.9300
N2—C51.318 (3)C8—C91.455 (4)
N2—H20.8600C8—H80.9300
N3—C41.375 (3)C9—C101.378 (4)
N3—C51.380 (3)C9—C141.384 (4)
N3—N41.390 (3)C10—C111.366 (4)
N4—C61.269 (4)C10—H100.9300
C1—C21.500 (4)C11—C121.345 (5)
C1—H1A0.9700C11—H110.9300
C1—H1B0.9700C12—C131.372 (5)
C2—C31.524 (4)C12—H120.9300
C2—H2A0.9700C13—C141.379 (5)
C2—H2B0.9700C13—H130.9300
C3—C41.484 (3)C14—H140.9300
C3—H3A0.9700
C1—O1—H1109.5N2—C5—N3103.2 (2)
C4—N1—N2103.6 (2)N2—C5—S1127.3 (2)
C5—N2—N1114.2 (2)N3—C5—S1129.4 (2)
C5—N2—H2122.9N4—C6—C7121.1 (3)
N1—N2—H2122.9N4—C6—H6119.4
C4—N3—C5107.6 (2)C7—C6—H6119.4
C4—N3—N4119.5 (2)C8—C7—C6122.7 (3)
C5—N3—N4132.1 (2)C8—C7—H7118.7
C6—N4—N3118.4 (2)C6—C7—H7118.7
O1—C1—C2109.4 (2)C7—C8—C9128.5 (3)
O1—C1—H1A109.8C7—C8—H8115.7
C2—C1—H1A109.8C9—C8—H8115.7
O1—C1—H1B109.8C10—C9—C14116.8 (3)
C2—C1—H1B109.8C10—C9—C8123.5 (3)
H1A—C1—H1B108.2C14—C9—C8119.7 (3)
C1—C2—C3113.3 (2)C11—C10—C9121.3 (3)
C1—C2—H2A108.9C11—C10—H10119.3
C3—C2—H2A108.9C9—C10—H10119.3
C1—C2—H2B108.9C12—C11—C10121.5 (3)
C3—C2—H2B108.9C12—C11—H11119.3
H2A—C2—H2B107.7C10—C11—H11119.3
C4—C3—C2112.2 (2)C11—C12—C13119.0 (3)
C4—C3—H3A109.2C11—C12—H12120.5
C2—C3—H3A109.2C13—C12—H12120.5
C4—C3—H3B109.2C12—C13—C14120.1 (4)
C2—C3—H3B109.2C12—C13—H13120.0
H3A—C3—H3B107.9C14—C13—H13120.0
N1—C4—N3111.3 (2)C13—C14—C9121.3 (3)
N1—C4—C3125.8 (2)C13—C14—H14119.4
N3—C4—C3122.9 (2)C9—C14—H14119.4
C4—N1—N2—C50.1 (3)N4—N3—C5—N2171.0 (2)
C4—N3—N4—C6162.4 (2)C4—N3—C5—S1176.4 (2)
C5—N3—N4—C629.2 (4)N4—N3—C5—S17.0 (4)
O1—C1—C2—C366.2 (3)N3—N4—C6—C7176.7 (2)
C1—C2—C3—C4175.2 (2)N4—C6—C7—C8176.1 (3)
N2—N1—C4—N31.2 (3)C6—C7—C8—C9175.8 (3)
N2—N1—C4—C3179.9 (2)C7—C8—C9—C101.8 (5)
C5—N3—C4—N11.8 (3)C7—C8—C9—C14178.1 (3)
N4—N3—C4—N1172.8 (2)C14—C9—C10—C111.5 (5)
C5—N3—C4—C3179.2 (2)C8—C9—C10—C11178.4 (3)
N4—N3—C4—C38.2 (4)C9—C10—C11—C120.2 (6)
C2—C3—C4—N12.2 (4)C10—C11—C12—C130.4 (6)
C2—C3—C4—N3176.5 (2)C11—C12—C13—C140.4 (6)
N1—N2—C5—N30.9 (3)C12—C13—C14—C91.8 (6)
N1—N2—C5—S1177.1 (2)C10—C9—C14—C132.3 (5)
C4—N3—C5—N21.6 (3)C8—C9—C14—C13177.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···S1i0.822.453.206 (2)154
N2—H2···O1ii0.862.012.821 (3)157
Symmetry codes: (i) x, y1, z; (ii) x1/2, y+1/2, z+2.
 

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