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
CCDC reference: 601112
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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-1
H-pyrazol-1-yl])acetate
top
Crystal data top
C13H18N4O2 | Z = 2 |
Mr = 262.31 | F(000) = 280 |
Triclinic, P1 | Dx = 1.288 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.616 (1) Å | Cell parameters from 9864 reflections |
b = 9.733 (2) Å | θ = 3.2–26.1° |
c = 9.902 (2) Å | µ = 0.09 mm−1 |
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 tube | Rint = 0.087 |
Graphite monochromator | θmax = 26.1°, θmin = 3.2° |
ω scans | h = −9→9 |
9864 measured reflections | k = −12→12 |
2670 independent reflections | l = −12→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N1 | −0.48205 (19) | 0.29805 (16) | 0.63397 (15) | 0.0282 (4) | |
N2 | −0.65692 (19) | 0.33414 (15) | 0.69745 (15) | 0.0280 (4) | |
N3 | −0.10453 (19) | 0.06941 (16) | 0.81425 (15) | 0.0288 (4) | |
N4 | 0.06942 (19) | 0.03833 (16) | 0.74599 (15) | 0.0287 (4) | |
O1 | 0.16001 (17) | −0.26533 (14) | 0.76502 (14) | 0.0370 (4) | |
O2 | 0.43825 (16) | −0.26198 (13) | 0.80615 (13) | 0.0331 (3) | |
C1 | −0.7899 (3) | 0.4345 (2) | 0.6131 (2) | 0.0372 (5) | |
H1A | −0.8641 | 0.3806 | 0.5885 | 0.056* | |
H1B | −0.7274 | 0.4895 | 0.5276 | 0.056* | |
H1C | −0.8662 | 0.4999 | 0.6673 | 0.056* | |
C2 | −0.6816 (2) | 0.27213 (18) | 0.83927 (19) | 0.0282 (4) | |
C3 | −0.8624 (3) | 0.2956 (2) | 0.9316 (2) | 0.0390 (5) | |
H3A | −0.9008 | 0.3974 | 0.9288 | 0.059* | |
H3B | −0.8519 | 0.2411 | 1.0278 | 0.059* | |
H3C | −0.9509 | 0.2632 | 0.8974 | 0.059* | |
C4 | −0.5148 (2) | 0.19234 (19) | 0.87099 (18) | 0.0283 (4) | |
H4 | −0.4871 | 0.1376 | 0.9600 | 0.034* | |
C5 | −0.3941 (2) | 0.21060 (18) | 0.74087 (18) | 0.0256 (4) | |
C6 | −0.1992 (2) | 0.15308 (18) | 0.70998 (18) | 0.0254 (4) | |
C7 | −0.0853 (2) | 0.17350 (18) | 0.57666 (18) | 0.0283 (4) | |
H7 | −0.1189 | 0.2269 | 0.4890 | 0.034* | |
C8 | 0.0849 (2) | 0.09853 (18) | 0.60272 (18) | 0.0277 (4) | |
C9 | 0.2627 (3) | 0.0796 (2) | 0.5058 (2) | 0.0373 (5) | |
H9A | 0.3456 | 0.1281 | 0.5276 | 0.056* | |
H9B | 0.2431 | 0.1209 | 0.4087 | 0.056* | |
H9C | 0.3136 | −0.0224 | 0.5188 | 0.056* | |
C10 | 0.2132 (2) | −0.0545 (2) | 0.8229 (2) | 0.0314 (4) | |
H10A | 0.1734 | −0.0640 | 0.9243 | 0.038* | |
H10B | 0.3204 | −0.0092 | 0.7953 | 0.038* | |
C11 | 0.2638 (2) | −0.2053 (2) | 0.79380 (17) | 0.0282 (4) | |
C12 | 0.5060 (3) | −0.4052 (2) | 0.7759 (2) | 0.0377 (5) | |
H12A | 0.5000 | −0.3993 | 0.6775 | 0.045* | |
H12B | 0.4318 | −0.4744 | 0.8370 | 0.045* | |
C13 | 0.6996 (3) | −0.4536 (2) | 0.8029 (3) | 0.0479 (6) | |
H13A | 0.7705 | −0.3821 | 0.7453 | 0.072* | |
H13B | 0.7492 | −0.5453 | 0.7790 | 0.072* | |
H13C | 0.7032 | −0.4643 | 0.9017 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0252 (8) | 0.0297 (8) | 0.0291 (8) | −0.0029 (6) | −0.0037 (6) | −0.0085 (6) |
N2 | 0.0263 (8) | 0.0259 (8) | 0.0314 (8) | −0.0024 (6) | −0.0038 (6) | −0.0089 (6) |
N3 | 0.0261 (8) | 0.0327 (9) | 0.0289 (8) | −0.0009 (6) | −0.0040 (6) | −0.0134 (6) |
N4 | 0.0236 (8) | 0.0307 (9) | 0.0326 (8) | 0.0005 (6) | −0.0041 (6) | −0.0138 (7) |
O1 | 0.0347 (8) | 0.0419 (8) | 0.0394 (8) | −0.0105 (6) | −0.0042 (6) | −0.0161 (6) |
O2 | 0.0279 (7) | 0.0302 (7) | 0.0426 (8) | −0.0003 (6) | −0.0044 (6) | −0.0159 (6) |
C1 | 0.0337 (11) | 0.0327 (11) | 0.0435 (11) | 0.0008 (8) | −0.0103 (9) | −0.0094 (9) |
C2 | 0.0294 (10) | 0.0253 (10) | 0.0314 (10) | −0.0086 (8) | −0.0016 (7) | −0.0087 (7) |
C3 | 0.0315 (11) | 0.0429 (12) | 0.0412 (12) | −0.0087 (9) | 0.0033 (8) | −0.0131 (9) |
C4 | 0.0318 (10) | 0.0253 (9) | 0.0269 (9) | −0.0058 (8) | −0.0031 (7) | −0.0056 (7) |
C5 | 0.0268 (10) | 0.0237 (9) | 0.0292 (9) | −0.0074 (7) | −0.0040 (7) | −0.0091 (7) |
C6 | 0.0264 (9) | 0.0226 (9) | 0.0297 (9) | −0.0046 (7) | −0.0050 (7) | −0.0098 (7) |
C7 | 0.0325 (10) | 0.0243 (9) | 0.0270 (9) | −0.0066 (8) | −0.0023 (7) | −0.0051 (7) |
C8 | 0.0286 (10) | 0.0237 (9) | 0.0306 (10) | −0.0070 (8) | 0.0015 (7) | −0.0092 (7) |
C9 | 0.0308 (10) | 0.0354 (11) | 0.0431 (11) | −0.0073 (8) | 0.0065 (8) | −0.0136 (9) |
C10 | 0.0267 (9) | 0.0356 (11) | 0.0351 (10) | 0.0013 (8) | −0.0080 (8) | −0.0168 (8) |
C11 | 0.0275 (10) | 0.0355 (10) | 0.0208 (9) | −0.0052 (8) | −0.0009 (7) | −0.0083 (7) |
C12 | 0.0382 (11) | 0.0275 (11) | 0.0477 (12) | −0.0017 (8) | −0.0020 (9) | −0.0164 (9) |
C13 | 0.0440 (13) | 0.0357 (12) | 0.0637 (15) | 0.0023 (10) | −0.0105 (11) | −0.0179 (10) |
Geometric parameters (Å, º) top
N3—N4 | 1.363 (2) | C10—C11 | 1.522 (2) |
N4—C8 | 1.364 (2) | C10—H10A | 0.9700 |
N4—C10 | 1.448 (2) | C10—H10B | 0.9700 |
O2—C11 | 1.332 (2) | C4—H4 | 0.9300 |
O2—C12 | 1.462 (2) | C1—H1A | 0.9600 |
N3—C6 | 1.346 (2) | C1—H1B | 0.9600 |
N2—C2 | 1.354 (2) | C1—H1C | 0.9600 |
N1—N2 | 1.3597 (19) | C12—C13 | 1.496 (3) |
N2—C1 | 1.453 (2) | C12—H12A | 0.9700 |
N1—C5 | 1.348 (2) | C12—H12B | 0.9700 |
O1—C11 | 1.205 (2) | C9—H9A | 0.9600 |
C8—C7 | 1.369 (2) | C9—H9B | 0.9600 |
C8—C9 | 1.492 (2) | C9—H9C | 0.9600 |
C6—C7 | 1.409 (2) | C3—H3A | 0.9600 |
C6—C5 | 1.460 (2) | C3—H3B | 0.9600 |
C2—C4 | 1.374 (2) | C3—H3C | 0.9600 |
C2—C3 | 1.492 (2) | C13—H13A | 0.9600 |
C5—C4 | 1.409 (2) | C13—H13B | 0.9600 |
C7—H7 | 0.9300 | C13—H13C | 0.9600 |
| | | |
N3—N4—C8 | 112.39 (14) | C2—C4—C5 | 105.83 (15) |
N3—N4—C10 | 121.07 (14) | C2—C4—H4 | 127.1 |
C8—N4—C10 | 126.49 (15) | C5—C4—H4 | 127.1 |
C11—O2—C12 | 115.88 (14) | N2—C1—H1A | 109.5 |
C6—N3—N4 | 104.33 (14) | N2—C1—H1B | 109.5 |
C2—N2—N1 | 112.60 (14) | H1A—C1—H1B | 109.5 |
C2—N2—C1 | 127.84 (15) | N2—C1—H1C | 109.5 |
N1—N2—C1 | 119.50 (14) | H1A—C1—H1C | 109.5 |
C5—N1—N2 | 104.58 (14) | H1B—C1—H1C | 109.5 |
N4—C8—C7 | 106.43 (15) | O2—C12—C13 | 107.92 (15) |
N4—C8—C9 | 122.04 (16) | O2—C12—H12A | 110.1 |
C7—C8—C9 | 131.53 (17) | C13—C12—H12A | 110.1 |
N3—C6—C7 | 111.02 (16) | O2—C12—H12B | 110.1 |
N3—C6—C5 | 121.19 (15) | C13—C12—H12B | 110.1 |
C7—C6—C5 | 127.80 (16) | H12A—C12—H12B | 108.4 |
N2—C2—C4 | 106.42 (15) | C8—C9—H9A | 109.5 |
N2—C2—C3 | 122.32 (16) | C8—C9—H9B | 109.5 |
C4—C2—C3 | 131.26 (17) | H9A—C9—H9B | 109.5 |
N1—C5—C4 | 110.57 (15) | C8—C9—H9C | 109.5 |
N1—C5—C6 | 119.17 (15) | H9A—C9—H9C | 109.5 |
C4—C5—C6 | 130.25 (16) | H9B—C9—H9C | 109.5 |
C8—C7—C6 | 105.83 (15) | C2—C3—H3A | 109.5 |
C8—C7—H7 | 127.1 | C2—C3—H3B | 109.5 |
C6—C7—H7 | 127.1 | H3A—C3—H3B | 109.5 |
N4—C10—C11 | 112.03 (14) | C2—C3—H3C | 109.5 |
N4—C10—H10A | 109.2 | H3A—C3—H3C | 109.5 |
C11—C10—H10A | 109.2 | H3B—C3—H3C | 109.5 |
N4—C10—H10B | 109.2 | C12—C13—H13A | 109.5 |
C11—C10—H10B | 109.2 | C12—C13—H13B | 109.5 |
H10A—C10—H10B | 107.9 | H13A—C13—H13B | 109.5 |
O1—C11—O2 | 124.85 (17) | C12—C13—H13C | 109.5 |
O1—C11—C10 | 124.70 (16) | H13A—C13—H13C | 109.5 |
O2—C11—C10 | 110.45 (14) | H13B—C13—H13C | 109.5 |
| | | |
C8—N4—N3—C6 | −0.78 (18) | N3—C6—C5—C4 | −1.0 (3) |
C10—N4—N3—C6 | −178.21 (14) | C7—C6—C5—C4 | 179.07 (16) |
C2—N2—N1—C5 | −0.34 (18) | N4—C8—C7—C6 | −0.47 (18) |
C1—N2—N1—C5 | 177.18 (14) | C9—C8—C7—C6 | −179.39 (17) |
N3—N4—C8—C7 | 0.80 (18) | N3—C6—C7—C8 | 0.01 (19) |
C10—N4—C8—C7 | 178.06 (15) | C5—C6—C7—C8 | 179.97 (16) |
N3—N4—C8—C9 | 179.84 (15) | N3—N4—C10—C11 | 105.50 (17) |
C10—N4—C8—C9 | −2.9 (3) | C8—N4—C10—C11 | −71.5 (2) |
N4—N3—C6—C7 | 0.45 (18) | C12—O2—C11—O1 | 2.7 (3) |
N4—N3—C6—C5 | −179.51 (14) | C12—O2—C11—C10 | −177.97 (14) |
N1—N2—C2—C4 | 0.51 (19) | N4—C10—C11—O1 | −29.7 (2) |
C1—N2—C2—C4 | −176.75 (16) | N4—C10—C11—O2 | 150.99 (15) |
N1—N2—C2—C3 | −179.82 (15) | N2—C2—C4—C5 | −0.45 (18) |
C1—N2—C2—C3 | 2.9 (3) | C3—C2—C4—C5 | 179.91 (17) |
N2—N1—C5—C4 | 0.03 (18) | N1—C5—C4—C2 | 0.27 (19) |
N2—N1—C5—C6 | −178.90 (14) | C6—C5—C4—C2 | 179.05 (17) |
N3—C6—C5—N1 | 177.71 (14) | C11—O2—C12—C13 | −177.01 (16) |
C7—C6—C5—N1 | −2.2 (3) | | |