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In the title compound, C13H18N4O2, the dihedral angle between the two planar pyrazole rings is 2.20 (9)°; the relative orientation of the rings is also characterized by a C-C-C-C torsion angle of 179.07 (16)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005290/bh6063sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005290/bh6063Isup2.hkl
Contains datablock I

CCDC reference: 601112

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.049
  • wR factor = 0.139
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

checkCIF publication errors

Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: Role of co-authors: AA: Synthesis (PhD student). SR: Chemistry, PhD advisor. AR: Structure interpretation. DE: Cif edition and artwork. MT & CB: crystal selection, data collection and structure determination.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: CrysAlis RED (Oxford Diffraction, 2004); cell refinement: CrysAlis RED; 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 for Windows (Version 1.075; Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Ethyl 2-(5,1',5'-trimethyl-3,3'-bi-1H-pyrazol-1-yl])acetate top
Crystal data top
C13H18N4O2Z = 2
Mr = 262.31F(000) = 280
Triclinic, P1Dx = 1.288 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.616 (1) ÅCell parameters from 9864 reflections
b = 9.733 (2) Åθ = 3.2–26.1°
c = 9.902 (2) ŵ = 0.09 mm1
α = 73.55 (2)°T = 173 K
β = 77.89 (1)°Parallelepiped, colourless
γ = 76.57 (2)°0.26 × 0.23 × 0.16 mm
V = 676.5 (2) Å3
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
2000 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.087
Graphite monochromatorθmax = 26.1°, θmin = 3.2°
ω scansh = 99
9864 measured reflectionsk = 1212
2670 independent reflectionsl = 1212
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0708P)2]
where P = (Fo2 + 2Fc2)/3
2670 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.24 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
N10.48205 (19)0.29805 (16)0.63397 (15)0.0282 (4)
N20.65692 (19)0.33414 (15)0.69745 (15)0.0280 (4)
N30.10453 (19)0.06941 (16)0.81425 (15)0.0288 (4)
N40.06942 (19)0.03833 (16)0.74599 (15)0.0287 (4)
O10.16001 (17)0.26533 (14)0.76502 (14)0.0370 (4)
O20.43825 (16)0.26198 (13)0.80615 (13)0.0331 (3)
C10.7899 (3)0.4345 (2)0.6131 (2)0.0372 (5)
H1A0.86410.38060.58850.056*
H1B0.72740.48950.52760.056*
H1C0.86620.49990.66730.056*
C20.6816 (2)0.27213 (18)0.83927 (19)0.0282 (4)
C30.8624 (3)0.2956 (2)0.9316 (2)0.0390 (5)
H3A0.90080.39740.92880.059*
H3B0.85190.24111.02780.059*
H3C0.95090.26320.89740.059*
C40.5148 (2)0.19234 (19)0.87099 (18)0.0283 (4)
H40.48710.13760.96000.034*
C50.3941 (2)0.21060 (18)0.74087 (18)0.0256 (4)
C60.1992 (2)0.15308 (18)0.70998 (18)0.0254 (4)
C70.0853 (2)0.17350 (18)0.57666 (18)0.0283 (4)
H70.11890.22690.48900.034*
C80.0849 (2)0.09853 (18)0.60272 (18)0.0277 (4)
C90.2627 (3)0.0796 (2)0.5058 (2)0.0373 (5)
H9A0.34560.12810.52760.056*
H9B0.24310.12090.40870.056*
H9C0.31360.02240.51880.056*
C100.2132 (2)0.0545 (2)0.8229 (2)0.0314 (4)
H10A0.17340.06400.92430.038*
H10B0.32040.00920.79530.038*
C110.2638 (2)0.2053 (2)0.79380 (17)0.0282 (4)
C120.5060 (3)0.4052 (2)0.7759 (2)0.0377 (5)
H12A0.50000.39930.67750.045*
H12B0.43180.47440.83700.045*
C130.6996 (3)0.4536 (2)0.8029 (3)0.0479 (6)
H13A0.77050.38210.74530.072*
H13B0.74920.54530.77900.072*
H13C0.70320.46430.90170.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0252 (8)0.0297 (8)0.0291 (8)0.0029 (6)0.0037 (6)0.0085 (6)
N20.0263 (8)0.0259 (8)0.0314 (8)0.0024 (6)0.0038 (6)0.0089 (6)
N30.0261 (8)0.0327 (9)0.0289 (8)0.0009 (6)0.0040 (6)0.0134 (6)
N40.0236 (8)0.0307 (9)0.0326 (8)0.0005 (6)0.0041 (6)0.0138 (7)
O10.0347 (8)0.0419 (8)0.0394 (8)0.0105 (6)0.0042 (6)0.0161 (6)
O20.0279 (7)0.0302 (7)0.0426 (8)0.0003 (6)0.0044 (6)0.0159 (6)
C10.0337 (11)0.0327 (11)0.0435 (11)0.0008 (8)0.0103 (9)0.0094 (9)
C20.0294 (10)0.0253 (10)0.0314 (10)0.0086 (8)0.0016 (7)0.0087 (7)
C30.0315 (11)0.0429 (12)0.0412 (12)0.0087 (9)0.0033 (8)0.0131 (9)
C40.0318 (10)0.0253 (9)0.0269 (9)0.0058 (8)0.0031 (7)0.0056 (7)
C50.0268 (10)0.0237 (9)0.0292 (9)0.0074 (7)0.0040 (7)0.0091 (7)
C60.0264 (9)0.0226 (9)0.0297 (9)0.0046 (7)0.0050 (7)0.0098 (7)
C70.0325 (10)0.0243 (9)0.0270 (9)0.0066 (8)0.0023 (7)0.0051 (7)
C80.0286 (10)0.0237 (9)0.0306 (10)0.0070 (8)0.0015 (7)0.0092 (7)
C90.0308 (10)0.0354 (11)0.0431 (11)0.0073 (8)0.0065 (8)0.0136 (9)
C100.0267 (9)0.0356 (11)0.0351 (10)0.0013 (8)0.0080 (8)0.0168 (8)
C110.0275 (10)0.0355 (10)0.0208 (9)0.0052 (8)0.0009 (7)0.0083 (7)
C120.0382 (11)0.0275 (11)0.0477 (12)0.0017 (8)0.0020 (9)0.0164 (9)
C130.0440 (13)0.0357 (12)0.0637 (15)0.0023 (10)0.0105 (11)0.0179 (10)
Geometric parameters (Å, º) top
N3—N41.363 (2)C10—C111.522 (2)
N4—C81.364 (2)C10—H10A0.9700
N4—C101.448 (2)C10—H10B0.9700
O2—C111.332 (2)C4—H40.9300
O2—C121.462 (2)C1—H1A0.9600
N3—C61.346 (2)C1—H1B0.9600
N2—C21.354 (2)C1—H1C0.9600
N1—N21.3597 (19)C12—C131.496 (3)
N2—C11.453 (2)C12—H12A0.9700
N1—C51.348 (2)C12—H12B0.9700
O1—C111.205 (2)C9—H9A0.9600
C8—C71.369 (2)C9—H9B0.9600
C8—C91.492 (2)C9—H9C0.9600
C6—C71.409 (2)C3—H3A0.9600
C6—C51.460 (2)C3—H3B0.9600
C2—C41.374 (2)C3—H3C0.9600
C2—C31.492 (2)C13—H13A0.9600
C5—C41.409 (2)C13—H13B0.9600
C7—H70.9300C13—H13C0.9600
N3—N4—C8112.39 (14)C2—C4—C5105.83 (15)
N3—N4—C10121.07 (14)C2—C4—H4127.1
C8—N4—C10126.49 (15)C5—C4—H4127.1
C11—O2—C12115.88 (14)N2—C1—H1A109.5
C6—N3—N4104.33 (14)N2—C1—H1B109.5
C2—N2—N1112.60 (14)H1A—C1—H1B109.5
C2—N2—C1127.84 (15)N2—C1—H1C109.5
N1—N2—C1119.50 (14)H1A—C1—H1C109.5
C5—N1—N2104.58 (14)H1B—C1—H1C109.5
N4—C8—C7106.43 (15)O2—C12—C13107.92 (15)
N4—C8—C9122.04 (16)O2—C12—H12A110.1
C7—C8—C9131.53 (17)C13—C12—H12A110.1
N3—C6—C7111.02 (16)O2—C12—H12B110.1
N3—C6—C5121.19 (15)C13—C12—H12B110.1
C7—C6—C5127.80 (16)H12A—C12—H12B108.4
N2—C2—C4106.42 (15)C8—C9—H9A109.5
N2—C2—C3122.32 (16)C8—C9—H9B109.5
C4—C2—C3131.26 (17)H9A—C9—H9B109.5
N1—C5—C4110.57 (15)C8—C9—H9C109.5
N1—C5—C6119.17 (15)H9A—C9—H9C109.5
C4—C5—C6130.25 (16)H9B—C9—H9C109.5
C8—C7—C6105.83 (15)C2—C3—H3A109.5
C8—C7—H7127.1C2—C3—H3B109.5
C6—C7—H7127.1H3A—C3—H3B109.5
N4—C10—C11112.03 (14)C2—C3—H3C109.5
N4—C10—H10A109.2H3A—C3—H3C109.5
C11—C10—H10A109.2H3B—C3—H3C109.5
N4—C10—H10B109.2C12—C13—H13A109.5
C11—C10—H10B109.2C12—C13—H13B109.5
H10A—C10—H10B107.9H13A—C13—H13B109.5
O1—C11—O2124.85 (17)C12—C13—H13C109.5
O1—C11—C10124.70 (16)H13A—C13—H13C109.5
O2—C11—C10110.45 (14)H13B—C13—H13C109.5
C8—N4—N3—C60.78 (18)N3—C6—C5—C41.0 (3)
C10—N4—N3—C6178.21 (14)C7—C6—C5—C4179.07 (16)
C2—N2—N1—C50.34 (18)N4—C8—C7—C60.47 (18)
C1—N2—N1—C5177.18 (14)C9—C8—C7—C6179.39 (17)
N3—N4—C8—C70.80 (18)N3—C6—C7—C80.01 (19)
C10—N4—C8—C7178.06 (15)C5—C6—C7—C8179.97 (16)
N3—N4—C8—C9179.84 (15)N3—N4—C10—C11105.50 (17)
C10—N4—C8—C92.9 (3)C8—N4—C10—C1171.5 (2)
N4—N3—C6—C70.45 (18)C12—O2—C11—O12.7 (3)
N4—N3—C6—C5179.51 (14)C12—O2—C11—C10177.97 (14)
N1—N2—C2—C40.51 (19)N4—C10—C11—O129.7 (2)
C1—N2—C2—C4176.75 (16)N4—C10—C11—O2150.99 (15)
N1—N2—C2—C3179.82 (15)N2—C2—C4—C50.45 (18)
C1—N2—C2—C32.9 (3)C3—C2—C4—C5179.91 (17)
N2—N1—C5—C40.03 (18)N1—C5—C4—C20.27 (19)
N2—N1—C5—C6178.90 (14)C6—C5—C4—C2179.05 (17)
N3—C6—C5—N1177.71 (14)C11—O2—C12—C13177.01 (16)
C7—C6—C5—N12.2 (3)
 

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