In the crystal structure of the title compound, C11H16N4O, the two pyrazole rings are coplanar, as indicated by both the dihedral angle of 0.8 (1)° between their mean planes and the N-C-C-N torsion angle of 179.81 (13)°.
Supporting information
CCDC reference: 608343
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C)= 0.003 Å
- R factor = 0.049
- wR factor = 0.125
- Data-to-parameter ratio = 14.4
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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.
Ramdani - contributes to the writing of the article and interpretation
of the results
Attayibat - student in phD , synthesis of samples
Radi - synthesis of samples and contributes to the writing of the article
Eddike - preparation of the paper (CIF file, Figure)
TILLARD and BELIN - crystals selection, data collection
and crystal 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 CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); 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 1.08; Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
2-(1',5',5-Trimethyl-3,3'-bi-1
H-pyrazol-1-yl)ethanol
top
Crystal data top
C11H16N4O | Z = 2 |
Mr = 220.28 | F(000) = 236 |
Triclinic, P1 | Dx = 1.332 Mg m−3 |
Hall symbol: -P1 | Melting point: 180 K |
a = 6.9135 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.3389 (8) Å | Cell parameters from 25 reflections |
c = 12.183 (1) Å | θ = 12–18° |
α = 86.09 (1)° | µ = 0.09 mm−1 |
β = 82.18 (1)° | T = 173 K |
γ = 63.75 (1)° | Parallelepiped, colourless |
V = 549.2 (1) Å3 | 0.35 × 0.30 × 0.12 mm |
Data collection top
Oxford Diffraction Xcalibur CCD diffractometer | 1797 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.077 |
Graphite monochromator | θmax = 26.1°, θmin = 3.1° |
ω scans | h = −8→8 |
7672 measured reflections | k = −9→9 |
2185 independent reflections | l = −15→15 |
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) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.2622P] where P = (Fo2 + 2Fc2)/3 |
2185 reflections | (Δ/σ)max < 0.001 |
152 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.27 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 | 0.1089 (2) | 0.5286 (2) | 0.27991 (11) | 0.0214 (3) | |
N2 | 0.2823 (2) | 0.3873 (2) | 0.32801 (11) | 0.0206 (3) | |
N3 | 0.0603 (2) | 1.0185 (2) | 0.17083 (11) | 0.0219 (3) | |
C8 | 0.1610 (2) | 0.6829 (2) | 0.25302 (12) | 0.0194 (3) | |
N4 | −0.1121 (2) | 1.1566 (2) | 0.12177 (11) | 0.0217 (3) | |
C9 | 0.0102 (3) | 0.8631 (2) | 0.19778 (12) | 0.0199 (3) | |
C3 | 0.2797 (3) | 0.1962 (2) | 0.36806 (14) | 0.0250 (4) | |
H3A | 0.4279 | 0.0926 | 0.3687 | 0.030* | |
H3B | 0.2113 | 0.1533 | 0.3174 | 0.030* | |
O | 0.2737 (2) | 0.2527 (2) | 0.55944 (11) | 0.0327 (3) | |
H | 0.180 (4) | 0.325 (4) | 0.613 (2) | 0.063 (8)* | |
C12 | −0.4687 (3) | 1.2162 (3) | 0.06510 (15) | 0.0284 (4) | |
H12A | −0.5394 | 1.3494 | 0.0968 | 0.043* | |
H12B | −0.5642 | 1.1518 | 0.0784 | 0.043* | |
H12C | −0.4330 | 1.2269 | −0.0133 | 0.043* | |
C13 | −0.1147 (3) | 1.3501 (3) | 0.08443 (15) | 0.0289 (4) | |
H13A | −0.0148 | 1.3748 | 0.1216 | 0.043* | |
H13B | −0.2585 | 1.4570 | 0.1012 | 0.043* | |
H13C | −0.0726 | 1.3463 | 0.0059 | 0.043* | |
C10 | −0.1920 (3) | 0.9024 (2) | 0.16588 (13) | 0.0224 (4) | |
H10 | −0.2616 | 0.8182 | 0.1756 | 0.027* | |
C11 | −0.2656 (3) | 1.0921 (2) | 0.11705 (13) | 0.0212 (4) | |
C5 | 0.4376 (3) | 0.4497 (2) | 0.33203 (13) | 0.0212 (4) | |
C7 | 0.3642 (3) | 0.6414 (2) | 0.28410 (13) | 0.0224 (4) | |
H7 | 0.4347 | 0.7248 | 0.2746 | 0.027* | |
C6 | 0.6437 (3) | 0.3240 (3) | 0.38051 (14) | 0.0273 (4) | |
H6A | 0.6122 | 0.3097 | 0.4590 | 0.041* | |
H6B | 0.7385 | 0.3891 | 0.3667 | 0.041* | |
H6C | 0.7131 | 0.1922 | 0.3471 | 0.041* | |
C4 | 0.1596 (3) | 0.2141 (3) | 0.48292 (15) | 0.0290 (4) | |
H4A | 0.0142 | 0.3240 | 0.4845 | 0.035* | |
H4B | 0.1475 | 0.0891 | 0.5031 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0195 (7) | 0.0206 (7) | 0.0212 (7) | −0.0052 (5) | −0.0062 (5) | 0.0005 (5) |
N2 | 0.0189 (7) | 0.0188 (7) | 0.0208 (7) | −0.0044 (5) | −0.0056 (5) | 0.0005 (5) |
N3 | 0.0211 (7) | 0.0219 (7) | 0.0198 (7) | −0.0069 (6) | −0.0028 (5) | 0.0012 (5) |
C8 | 0.0188 (8) | 0.0192 (8) | 0.0163 (7) | −0.0050 (6) | −0.0007 (6) | −0.0016 (6) |
N4 | 0.0214 (7) | 0.0201 (7) | 0.0207 (7) | −0.0063 (6) | −0.0040 (5) | 0.0016 (5) |
C9 | 0.0202 (8) | 0.0195 (8) | 0.0166 (7) | −0.0058 (6) | −0.0005 (6) | −0.0023 (6) |
C3 | 0.0290 (9) | 0.0179 (8) | 0.0276 (9) | −0.0084 (7) | −0.0092 (7) | 0.0017 (6) |
O | 0.0255 (6) | 0.0446 (8) | 0.0259 (7) | −0.0129 (6) | −0.0060 (5) | 0.0021 (6) |
C12 | 0.0238 (9) | 0.0294 (9) | 0.0268 (9) | −0.0054 (7) | −0.0084 (7) | −0.0017 (7) |
C13 | 0.0341 (10) | 0.0229 (9) | 0.0294 (9) | −0.0122 (8) | −0.0056 (7) | 0.0038 (7) |
C10 | 0.0220 (8) | 0.0218 (8) | 0.0229 (8) | −0.0091 (7) | −0.0032 (6) | −0.0001 (6) |
C11 | 0.0211 (8) | 0.0217 (8) | 0.0174 (7) | −0.0057 (6) | −0.0025 (6) | −0.0029 (6) |
C5 | 0.0193 (8) | 0.0235 (8) | 0.0187 (7) | −0.0071 (7) | −0.0025 (6) | −0.0031 (6) |
C7 | 0.0209 (8) | 0.0224 (8) | 0.0239 (8) | −0.0094 (7) | −0.0029 (6) | −0.0002 (6) |
C6 | 0.0218 (8) | 0.0288 (9) | 0.0276 (9) | −0.0062 (7) | −0.0085 (7) | −0.0004 (7) |
C4 | 0.0272 (9) | 0.0275 (9) | 0.0338 (9) | −0.0129 (7) | −0.0093 (7) | 0.0080 (7) |
Geometric parameters (Å, º) top
N1—C8 | 1.341 (2) | C12—H12A | 0.9600 |
N1—N2 | 1.3650 (18) | C12—H12B | 0.9600 |
N2—C5 | 1.348 (2) | C12—H12C | 0.9600 |
N2—C3 | 1.460 (2) | C13—H13A | 0.9600 |
N3—C9 | 1.340 (2) | C13—H13B | 0.9600 |
N3—N4 | 1.3595 (19) | C13—H13C | 0.9600 |
C8—C7 | 1.400 (2) | C10—C11 | 1.376 (2) |
C8—C9 | 1.463 (2) | C10—H10 | 0.9300 |
N4—C11 | 1.349 (2) | C5—C7 | 1.384 (2) |
N4—C13 | 1.455 (2) | C5—C6 | 1.491 (2) |
C9—C10 | 1.402 (2) | C7—H7 | 0.9300 |
C3—C4 | 1.509 (2) | C6—H6A | 0.9600 |
C3—H3A | 0.9700 | C6—H6B | 0.9600 |
C3—H3B | 0.9700 | C6—H6C | 0.9600 |
O—C4 | 1.416 (2) | C4—H4A | 0.9700 |
O—H | 0.87 (3) | C4—H4B | 0.9700 |
C12—C11 | 1.494 (2) | | |
| | | |
C8—N1—N2 | 104.42 (13) | H13A—C13—H13B | 109.5 |
C5—N2—N1 | 112.34 (13) | N4—C13—H13C | 109.5 |
C5—N2—C3 | 128.51 (14) | H13A—C13—H13C | 109.5 |
N1—N2—C3 | 119.15 (13) | H13B—C13—H13C | 109.5 |
C9—N3—N4 | 104.26 (13) | C11—C10—C9 | 105.31 (15) |
N1—C8—C7 | 111.36 (14) | C11—C10—H10 | 127.3 |
N1—C8—C9 | 119.42 (14) | C9—C10—H10 | 127.3 |
C7—C8—C9 | 129.22 (15) | N4—C11—C10 | 106.54 (14) |
C11—N4—N3 | 112.60 (13) | N4—C11—C12 | 122.44 (15) |
C11—N4—C13 | 128.28 (14) | C10—C11—C12 | 131.02 (16) |
N3—N4—C13 | 119.10 (14) | N2—C5—C7 | 106.63 (14) |
N3—C9—C10 | 111.29 (14) | N2—C5—C6 | 123.10 (15) |
N3—C9—C8 | 119.90 (15) | C7—C5—C6 | 130.27 (16) |
C10—C9—C8 | 128.80 (15) | C5—C7—C8 | 105.25 (15) |
N2—C3—C4 | 112.40 (13) | C5—C7—H7 | 127.4 |
N2—C3—H3A | 109.1 | C8—C7—H7 | 127.4 |
C4—C3—H3A | 109.1 | C5—C6—H6A | 109.5 |
N2—C3—H3B | 109.1 | C5—C6—H6B | 109.5 |
C4—C3—H3B | 109.1 | H6A—C6—H6B | 109.5 |
H3A—C3—H3B | 107.9 | C5—C6—H6C | 109.5 |
C4—O—H | 108.2 (18) | H6A—C6—H6C | 109.5 |
C11—C12—H12A | 109.5 | H6B—C6—H6C | 109.5 |
C11—C12—H12B | 109.5 | O—C4—C3 | 109.39 (14) |
H12A—C12—H12B | 109.5 | O—C4—H4A | 109.8 |
C11—C12—H12C | 109.5 | C3—C4—H4A | 109.8 |
H12A—C12—H12C | 109.5 | O—C4—H4B | 109.8 |
H12B—C12—H12C | 109.5 | C3—C4—H4B | 109.8 |
N4—C13—H13A | 109.5 | H4A—C4—H4B | 108.2 |
N4—C13—H13B | 109.5 | | |
| | | |
C8—N1—N2—C5 | 0.30 (16) | N3—N4—C11—C10 | 0.32 (17) |
C8—N1—N2—C3 | 179.91 (13) | C13—N4—C11—C10 | −178.00 (15) |
N2—N1—C8—C7 | −0.35 (17) | N3—N4—C11—C12 | −178.96 (13) |
N2—N1—C8—C9 | 179.36 (12) | C13—N4—C11—C12 | 2.7 (2) |
C9—N3—N4—C11 | −0.27 (17) | C9—C10—C11—N4 | −0.23 (17) |
C9—N3—N4—C13 | 178.23 (13) | C9—C10—C11—C12 | 178.96 (16) |
N4—N3—C9—C10 | 0.11 (17) | N1—N2—C5—C7 | −0.13 (17) |
N4—N3—C9—C8 | 179.90 (12) | C3—N2—C5—C7 | −179.70 (14) |
N1—C8—C9—N3 | 179.81 (13) | N1—N2—C5—C6 | 179.99 (14) |
C7—C8—C9—N3 | −0.5 (2) | C3—N2—C5—C6 | 0.4 (2) |
N1—C8—C9—C10 | −0.4 (2) | N2—C5—C7—C8 | −0.08 (17) |
C7—C8—C9—C10 | 179.22 (16) | C6—C5—C7—C8 | 179.78 (16) |
C5—N2—C3—C4 | 95.56 (19) | N1—C8—C7—C5 | 0.28 (18) |
N1—N2—C3—C4 | −83.98 (17) | C9—C8—C7—C5 | −179.39 (15) |
N3—C9—C10—C11 | 0.08 (18) | N2—C3—C4—O | −65.80 (18) |
C8—C9—C10—C11 | −179.70 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O—H···N1i | 0.87 (3) | 2.10 (3) | 2.9441 (19) | 162 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |