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In the title compound, C11H11N3O2, the dihedral angles made by the planes of the triazole and benzene rings with the plane through the OC3 atoms of the ketone group are 72.87 (4) and 7.10 (3)°, respectively. There are some intermolecular interactions in the crystal structure, which contribute to the stability.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001169/hg6135sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001169/hg6135Isup2.hkl
Contains datablock I

CCDC reference: 264061

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.076
  • Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
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 27.85 From the CIF: _reflns_number_total 1271 Count of symmetry unique reflns 1274 Completeness (_total/calc) 99.76% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-(4-Hydroxyphenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one top
Crystal data top
C11H11N3O2F(000) = 456
Mr = 217.23Dx = 1.356 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1098 reflections
a = 22.759 (4) Åθ = 3.6–26.7°
b = 5.5729 (9) ŵ = 0.10 mm1
c = 8.3902 (14) ÅT = 293 K
β = 90.929 (2)°Plate, colorless
V = 1064.0 (3) Å30.28 × 0.22 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1271 independent reflections
Radiation source: fine-focus sealed tube1006 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2921
Tmin = 0.958, Tmax = 0.981k = 77
3413 measured reflectionsl = 911
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0423P)2 + 0.0744P]
where P = (Fo2 + 2Fc2)/3
1271 reflections(Δ/σ)max = 0.001
149 parametersΔρmax = 0.12 e Å3
3 restraintsΔρmin = 0.13 e Å3
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
N10.14909 (8)0.2545 (3)0.1435 (2)0.0422 (4)
N20.17183 (8)0.0500 (3)0.0831 (2)0.0547 (5)
N30.21645 (8)0.3727 (3)0.0190 (2)0.0518 (5)
O10.03756 (7)0.5294 (3)0.0556 (2)0.0598 (5)
O20.21274 (6)0.1802 (3)0.17034 (17)0.0532 (4)
H20.2324 (10)0.073 (4)0.120 (3)0.069 (9)*
C10.01373 (9)0.3386 (4)0.0832 (2)0.0429 (5)
C20.04437 (9)0.1561 (4)0.1890 (3)0.0470 (5)
H2A0.05190.01250.12730.056*
H2B0.01850.11260.27510.056*
C30.10210 (10)0.2470 (4)0.2596 (2)0.0504 (5)
H3A0.09620.40690.30210.060*
H3B0.11400.14350.34740.060*
C40.21187 (10)0.1313 (4)0.0136 (3)0.0564 (6)
H40.23530.03050.07380.068*
C50.17636 (9)0.4422 (4)0.0827 (2)0.0463 (5)
H50.16830.60110.10820.056*
C60.04500 (8)0.2822 (4)0.0161 (2)0.0384 (4)
C70.07716 (9)0.0807 (4)0.0587 (2)0.0462 (5)
H70.06060.03100.12840.055*
C80.13323 (9)0.0440 (4)0.0007 (3)0.0480 (5)
H80.15430.09050.03060.058*
C90.15838 (8)0.2058 (4)0.1068 (2)0.0413 (5)
C100.12644 (9)0.4057 (4)0.1531 (3)0.0477 (5)
H100.14250.51360.22620.057*
C110.07100 (9)0.4437 (4)0.0906 (2)0.0456 (5)
H110.05040.58020.12030.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0343 (8)0.0424 (9)0.0498 (9)0.0005 (7)0.0046 (7)0.0051 (7)
N20.0485 (11)0.0427 (9)0.0730 (14)0.0028 (9)0.0049 (10)0.0103 (9)
N30.0374 (9)0.0585 (11)0.0595 (11)0.0056 (9)0.0024 (8)0.0010 (9)
O10.0462 (9)0.0521 (9)0.0807 (11)0.0142 (7)0.0069 (7)0.0130 (8)
O20.0383 (9)0.0641 (10)0.0572 (9)0.0041 (7)0.0025 (7)0.0040 (8)
C10.0385 (11)0.0434 (10)0.0469 (12)0.0021 (9)0.0043 (9)0.0003 (9)
C20.0386 (11)0.0506 (11)0.0518 (12)0.0009 (9)0.0043 (9)0.0063 (10)
C30.0414 (11)0.0658 (13)0.0439 (11)0.0032 (10)0.0009 (9)0.0016 (10)
C40.0429 (12)0.0578 (13)0.0686 (15)0.0013 (11)0.0063 (11)0.0145 (12)
C50.0389 (11)0.0419 (10)0.0579 (14)0.0015 (9)0.0073 (10)0.0003 (10)
C60.0352 (11)0.0406 (11)0.0395 (11)0.0012 (8)0.0041 (8)0.0013 (8)
C70.0426 (12)0.0432 (11)0.0529 (13)0.0036 (9)0.0003 (10)0.0080 (9)
C80.0426 (12)0.0439 (11)0.0575 (13)0.0073 (10)0.0016 (9)0.0076 (10)
C90.0346 (11)0.0459 (11)0.0435 (11)0.0006 (9)0.0038 (8)0.0051 (9)
C100.0441 (12)0.0474 (12)0.0517 (13)0.0020 (10)0.0002 (10)0.0107 (10)
C110.0416 (11)0.0426 (11)0.0527 (12)0.0073 (9)0.0053 (9)0.0076 (9)
Geometric parameters (Å, º) top
N1—C51.323 (3)C3—H3A0.9700
N1—N21.354 (2)C3—H3B0.9700
N1—C31.459 (3)C4—H40.9300
N2—C41.311 (3)C5—H50.9300
N3—C51.317 (3)C6—C71.390 (3)
N3—C41.350 (3)C6—C111.395 (3)
O1—C11.218 (2)C7—C81.378 (3)
O2—C91.347 (2)C7—H70.9300
O2—H20.857 (10)C8—C91.384 (3)
C1—C61.476 (3)C8—H80.9300
C1—C21.513 (3)C9—C101.389 (3)
C2—C31.519 (3)C10—C111.375 (3)
C2—H2A0.9700C10—H100.9300
C2—H2B0.9700C11—H110.9300
C5—N1—N2109.66 (17)N3—C4—H4122.6
C5—N1—C3129.36 (18)N3—C5—N1110.61 (19)
N2—N1—C3120.98 (17)N3—C5—H5124.7
C4—N2—N1102.39 (17)N1—C5—H5124.7
C5—N3—C4102.49 (18)C7—C6—C11117.82 (17)
C9—O2—H2111.2 (18)C7—C6—C1123.46 (17)
O1—C1—C6121.13 (18)C11—C6—C1118.66 (17)
O1—C1—C2119.75 (18)C8—C7—C6121.02 (19)
C6—C1—C2119.12 (17)C8—C7—H7119.5
C1—C2—C3113.09 (18)C6—C7—H7119.5
C1—C2—H2A109.0C7—C8—C9120.4 (2)
C3—C2—H2A109.0C7—C8—H8119.8
C1—C2—H2B109.0C9—C8—H8119.8
C3—C2—H2B109.0O2—C9—C8123.56 (19)
H2A—C2—H2B107.8O2—C9—C10117.12 (17)
N1—C3—C2112.83 (17)C8—C9—C10119.31 (18)
N1—C3—H3A109.0C11—C10—C9119.90 (18)
C2—C3—H3A109.0C11—C10—H10120.1
N1—C3—H3B109.0C9—C10—H10120.1
C2—C3—H3B109.0C10—C11—C6121.48 (18)
H3A—C3—H3B107.8C10—C11—H11119.3
N2—C4—N3114.9 (2)C6—C11—H11119.3
N2—C4—H4122.6
C5—N1—N2—C40.6 (2)C2—C1—C6—C77.5 (3)
C3—N1—N2—C4179.81 (19)O1—C1—C6—C115.2 (3)
O1—C1—C2—C34.1 (3)C2—C1—C6—C11175.30 (18)
C6—C1—C2—C3175.41 (17)C11—C6—C7—C81.0 (3)
C5—N1—C3—C2112.7 (2)C1—C6—C7—C8176.2 (2)
N2—N1—C3—C268.2 (2)C6—C7—C8—C91.1 (3)
C1—C2—C3—N174.4 (2)C7—C8—C9—O2179.5 (2)
N1—N2—C4—N30.1 (2)C7—C8—C9—C100.2 (3)
C5—N3—C4—N20.3 (3)O2—C9—C10—C11179.09 (19)
C4—N3—C5—N10.7 (2)C8—C9—C10—C111.5 (3)
N2—N1—C5—N30.9 (2)C9—C10—C11—C61.6 (3)
C3—N1—C5—N3179.99 (19)C7—C6—C11—C100.4 (3)
O1—C1—C6—C7172.0 (2)C1—C6—C11—C10177.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N3i0.86 (1)1.83 (1)2.685 (2)172 (3)
C3—H3A···O1ii0.972.553.162 (3)120
C3—H3B···N2iii0.972.593.534 (3)163
C4—H4···O2iv0.932.433.327 (3)162
C5—H5···N2v0.932.513.389 (5)157
Symmetry codes: (i) x1/2, y1/2, z; (ii) x, y+1, z+1/2; (iii) x, y, z+1/2; (iv) x+1/2, y1/2, z; (v) x, y+1, z.
 

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