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In the mol­ecule of the title compound, C12H13N3O2, the benzene and triazole rings are each planar and form a dihedral angle of 18.36 (9)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026225/hk2074sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026225/hk2074Isup2.hkl
Contains datablock I

CCDC reference: 618234

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.116
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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).

Ethyl 2-(4-phenyl-1H-1,2,3-triazol-1-yl)acetate top
Crystal data top
C12H13N3O2Z = 2
Mr = 231.25F(000) = 244
Triclinic, P1Dx = 1.330 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.6646 (15) ÅCell parameters from 1283 reflections
b = 8.644 (2) Åθ = 2.4–24.8°
c = 12.393 (3) ŵ = 0.09 mm1
α = 85.549 (4)°T = 294 K
β = 81.179 (4)°Needle, colorless
γ = 74.569 (4)°0.38 × 0.19 × 0.14 mm
V = 577.6 (3) Å3
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2209 independent reflections
Radiation source: fine-focus sealed tube1811 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 1.7°
ω scansh = 66
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
k = 109
Tmin = 0.965, Tmax = 0.987l = 1514
3338 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0547P)2 + 0.0941P]
where P = (Fo2 + 2Fc2)/3
2209 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.25 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
O10.3106 (3)0.66923 (15)0.85611 (10)0.0687 (4)
O20.3060 (2)0.85578 (14)0.97312 (9)0.0600 (4)
N10.2580 (2)0.88594 (19)0.64220 (12)0.0582 (4)
N20.2136 (2)0.93942 (18)0.73113 (12)0.0607 (4)
N30.0338 (2)0.90674 (16)0.72542 (10)0.0476 (3)
C10.1895 (3)0.6341 (2)0.43371 (14)0.0535 (4)
H1A0.32870.61430.46900.064*
C20.2009 (4)0.5560 (2)0.33951 (16)0.0648 (5)
H2A0.34770.48450.31140.078*
C30.0043 (4)0.5834 (2)0.28685 (15)0.0667 (5)
H3A0.00240.52900.22410.080*
C40.2194 (4)0.6919 (2)0.32757 (14)0.0650 (5)
H4A0.35760.71160.29160.078*
C50.2314 (3)0.7717 (2)0.42142 (13)0.0537 (4)
H5A0.37700.84570.44780.064*
C60.0272 (3)0.74203 (18)0.47663 (12)0.0437 (4)
C70.0396 (3)0.81844 (18)0.57994 (12)0.0428 (4)
C80.1456 (3)0.83287 (19)0.63369 (12)0.0471 (4)
H8A0.31490.79840.61110.056*
C90.1435 (3)0.9495 (2)0.81298 (13)0.0532 (4)
H9A0.01681.02320.85960.064*
H9B0.26781.00490.78200.064*
C100.2613 (3)0.8057 (2)0.88143 (13)0.0486 (4)
C110.4464 (4)0.7350 (2)1.04458 (15)0.0667 (5)
H11A0.39970.63501.04360.080*
H11B0.40820.77081.11900.080*
C120.7151 (4)0.7079 (3)1.00768 (18)0.0757 (6)
H12A0.80520.62781.05480.114*
H12B0.76160.80651.01020.114*
H12C0.75270.67190.93420.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0864 (10)0.0537 (8)0.0665 (8)0.0097 (6)0.0242 (7)0.0080 (6)
O20.0633 (8)0.0633 (8)0.0489 (7)0.0001 (6)0.0196 (6)0.0101 (5)
N10.0401 (8)0.0765 (10)0.0554 (9)0.0061 (7)0.0103 (6)0.0100 (7)
N20.0430 (8)0.0793 (11)0.0539 (9)0.0024 (7)0.0066 (6)0.0139 (7)
N30.0426 (7)0.0534 (8)0.0452 (7)0.0073 (6)0.0092 (6)0.0037 (6)
C10.0496 (9)0.0557 (10)0.0545 (10)0.0093 (8)0.0118 (8)0.0039 (8)
C20.0723 (12)0.0577 (11)0.0599 (11)0.0098 (9)0.0038 (9)0.0101 (8)
C30.0927 (15)0.0690 (12)0.0461 (10)0.0314 (11)0.0122 (10)0.0059 (8)
C40.0713 (12)0.0857 (14)0.0492 (10)0.0343 (11)0.0230 (9)0.0081 (9)
C50.0486 (9)0.0662 (11)0.0477 (9)0.0160 (8)0.0126 (7)0.0053 (8)
C60.0451 (8)0.0450 (8)0.0429 (8)0.0155 (7)0.0090 (6)0.0058 (6)
C70.0380 (8)0.0464 (8)0.0428 (8)0.0093 (6)0.0074 (6)0.0027 (6)
C80.0386 (8)0.0568 (9)0.0440 (9)0.0088 (7)0.0052 (6)0.0044 (7)
C90.0588 (10)0.0541 (10)0.0472 (9)0.0099 (8)0.0147 (8)0.0079 (7)
C100.0449 (9)0.0551 (10)0.0444 (9)0.0091 (7)0.0056 (7)0.0073 (7)
C110.0684 (12)0.0764 (13)0.0487 (10)0.0027 (9)0.0177 (9)0.0001 (9)
C120.0668 (13)0.0815 (14)0.0760 (13)0.0060 (10)0.0242 (10)0.0028 (11)
Geometric parameters (Å, º) top
O1—C101.1934 (19)C4—H4A0.9300
O2—C101.3287 (19)C5—C61.389 (2)
O2—C111.462 (2)C5—H5A0.9300
N1—N21.3105 (19)C6—C71.470 (2)
N1—C71.364 (2)C7—C81.363 (2)
N2—N31.3456 (19)C8—H8A0.9300
N3—C81.333 (2)C9—C101.509 (2)
N3—C91.446 (2)C9—H9A0.9700
C1—C21.378 (2)C9—H9B0.9700
C1—C61.388 (2)C11—C121.481 (3)
C1—H1A0.9300C11—H11A0.9700
C2—C31.377 (3)C11—H11B0.9700
C2—H2A0.9300C12—H12A0.9600
C3—C41.377 (3)C12—H12B0.9600
C3—H3A0.9300C12—H12C0.9600
C4—C51.381 (2)
C10—O2—C11117.20 (13)N1—C7—C6122.53 (14)
N2—N1—C7109.41 (13)N3—C8—C7105.69 (14)
N1—N2—N3106.63 (13)N3—C8—H8A127.2
C8—N3—N2110.91 (13)C7—C8—H8A127.2
C8—N3—C9128.81 (14)N3—C9—C10112.83 (13)
N2—N3—C9120.28 (13)N3—C9—H9A109.0
C2—C1—C6120.86 (16)C10—C9—H9A109.0
C2—C1—H1A119.6N3—C9—H9B109.0
C6—C1—H1A119.6C10—C9—H9B109.0
C3—C2—C1120.16 (18)H9A—C9—H9B107.8
C3—C2—H2A119.9O1—C10—O2125.54 (16)
C1—C2—H2A119.9O1—C10—C9125.33 (15)
C2—C3—C4119.62 (17)O2—C10—C9109.11 (13)
C2—C3—H3A120.2O2—C11—C12110.24 (16)
C4—C3—H3A120.2O2—C11—H11A109.6
C3—C4—C5120.49 (17)C12—C11—H11A109.6
C3—C4—H4A119.8O2—C11—H11B109.6
C5—C4—H4A119.8C12—C11—H11B109.6
C4—C5—C6120.35 (17)H11A—C11—H11B108.1
C4—C5—H5A119.8C11—C12—H12A109.5
C6—C5—H5A119.8C11—C12—H12B109.5
C1—C6—C5118.49 (15)H12A—C12—H12B109.5
C1—C6—C7120.09 (14)C11—C12—H12C109.5
C5—C6—C7121.39 (15)H12A—C12—H12C109.5
C8—C7—N1107.36 (14)H12B—C12—H12C109.5
C8—C7—C6130.08 (14)
C7—N1—N2—N30.30 (19)C5—C6—C7—C8164.44 (16)
N1—N2—N3—C80.10 (19)C1—C6—C7—N1160.17 (15)
N1—N2—N3—C9179.25 (14)C5—C6—C7—N118.0 (2)
C6—C1—C2—C30.4 (3)N2—N3—C8—C70.14 (18)
C1—C2—C3—C41.3 (3)C9—N3—C8—C7178.92 (14)
C2—C3—C4—C50.8 (3)N1—C7—C8—N30.32 (17)
C3—C4—C5—C60.8 (3)C6—C7—C8—N3177.56 (15)
C2—C1—C6—C51.1 (2)C8—N3—C9—C1071.8 (2)
C2—C1—C6—C7177.09 (15)N2—N3—C9—C10107.23 (17)
C4—C5—C6—C11.7 (2)C11—O2—C10—O15.6 (2)
C4—C5—C6—C7176.49 (14)C11—O2—C10—C9173.05 (14)
N2—N1—C7—C80.40 (19)N3—C9—C10—O115.5 (2)
N2—N1—C7—C6177.68 (14)N3—C9—C10—O2165.78 (13)
C1—C6—C7—C817.4 (2)C10—O2—C11—C1283.9 (2)
 

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