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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012864/hg2018sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012864/hg2018IIsup2.hkl
Contains datablock II

CCDC reference: 608343

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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.
Author Response: .
 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

Computing details top

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-1H-pyrazol-1-yl)ethanol top
Crystal data top
C11H16N4OZ = 2
Mr = 220.28F(000) = 236
Triclinic, P1Dx = 1.332 Mg m3
Hall symbol: -P1Melting point: 180 K
a = 6.9135 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.3389 (8) ÅCell parameters from 25 reflections
c = 12.183 (1) Åθ = 12–18°
α = 86.09 (1)°µ = 0.09 mm1
β = 82.18 (1)°T = 173 K
γ = 63.75 (1)°Parallelepiped, colourless
V = 549.2 (1) Å30.35 × 0.30 × 0.12 mm
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
1797 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.077
Graphite monochromatorθmax = 26.1°, θmin = 3.1°
ω scansh = 88
7672 measured reflectionsk = 99
2185 independent reflectionsl = 1515
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) = 0.125H 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 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.27 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
N10.1089 (2)0.5286 (2)0.27991 (11)0.0214 (3)
N20.2823 (2)0.3873 (2)0.32801 (11)0.0206 (3)
N30.0603 (2)1.0185 (2)0.17083 (11)0.0219 (3)
C80.1610 (2)0.6829 (2)0.25302 (12)0.0194 (3)
N40.1121 (2)1.1566 (2)0.12177 (11)0.0217 (3)
C90.0102 (3)0.8631 (2)0.19778 (12)0.0199 (3)
C30.2797 (3)0.1962 (2)0.36806 (14)0.0250 (4)
H3A0.42790.09260.36870.030*
H3B0.21130.15330.31740.030*
O0.2737 (2)0.2527 (2)0.55944 (11)0.0327 (3)
H0.180 (4)0.325 (4)0.613 (2)0.063 (8)*
C120.4687 (3)1.2162 (3)0.06510 (15)0.0284 (4)
H12A0.53941.34940.09680.043*
H12B0.56421.15180.07840.043*
H12C0.43301.22690.01330.043*
C130.1147 (3)1.3501 (3)0.08443 (15)0.0289 (4)
H13A0.01481.37480.12160.043*
H13B0.25851.45700.10120.043*
H13C0.07261.34630.00590.043*
C100.1920 (3)0.9024 (2)0.16588 (13)0.0224 (4)
H100.26160.81820.17560.027*
C110.2656 (3)1.0921 (2)0.11705 (13)0.0212 (4)
C50.4376 (3)0.4497 (2)0.33203 (13)0.0212 (4)
C70.3642 (3)0.6414 (2)0.28410 (13)0.0224 (4)
H70.43470.72480.27460.027*
C60.6437 (3)0.3240 (3)0.38051 (14)0.0273 (4)
H6A0.61220.30970.45900.041*
H6B0.73850.38910.36670.041*
H6C0.71310.19220.34710.041*
C40.1596 (3)0.2141 (3)0.48292 (15)0.0290 (4)
H4A0.01420.32400.48450.035*
H4B0.14750.08910.50310.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0195 (7)0.0206 (7)0.0212 (7)0.0052 (5)0.0062 (5)0.0005 (5)
N20.0189 (7)0.0188 (7)0.0208 (7)0.0044 (5)0.0056 (5)0.0005 (5)
N30.0211 (7)0.0219 (7)0.0198 (7)0.0069 (6)0.0028 (5)0.0012 (5)
C80.0188 (8)0.0192 (8)0.0163 (7)0.0050 (6)0.0007 (6)0.0016 (6)
N40.0214 (7)0.0201 (7)0.0207 (7)0.0063 (6)0.0040 (5)0.0016 (5)
C90.0202 (8)0.0195 (8)0.0166 (7)0.0058 (6)0.0005 (6)0.0023 (6)
C30.0290 (9)0.0179 (8)0.0276 (9)0.0084 (7)0.0092 (7)0.0017 (6)
O0.0255 (6)0.0446 (8)0.0259 (7)0.0129 (6)0.0060 (5)0.0021 (6)
C120.0238 (9)0.0294 (9)0.0268 (9)0.0054 (7)0.0084 (7)0.0017 (7)
C130.0341 (10)0.0229 (9)0.0294 (9)0.0122 (8)0.0056 (7)0.0038 (7)
C100.0220 (8)0.0218 (8)0.0229 (8)0.0091 (7)0.0032 (6)0.0001 (6)
C110.0211 (8)0.0217 (8)0.0174 (7)0.0057 (6)0.0025 (6)0.0029 (6)
C50.0193 (8)0.0235 (8)0.0187 (7)0.0071 (7)0.0025 (6)0.0031 (6)
C70.0209 (8)0.0224 (8)0.0239 (8)0.0094 (7)0.0029 (6)0.0002 (6)
C60.0218 (8)0.0288 (9)0.0276 (9)0.0062 (7)0.0085 (7)0.0004 (7)
C40.0272 (9)0.0275 (9)0.0338 (9)0.0129 (7)0.0093 (7)0.0080 (7)
Geometric parameters (Å, º) top
N1—C81.341 (2)C12—H12A0.9600
N1—N21.3650 (18)C12—H12B0.9600
N2—C51.348 (2)C12—H12C0.9600
N2—C31.460 (2)C13—H13A0.9600
N3—C91.340 (2)C13—H13B0.9600
N3—N41.3595 (19)C13—H13C0.9600
C8—C71.400 (2)C10—C111.376 (2)
C8—C91.463 (2)C10—H100.9300
N4—C111.349 (2)C5—C71.384 (2)
N4—C131.455 (2)C5—C61.491 (2)
C9—C101.402 (2)C7—H70.9300
C3—C41.509 (2)C6—H6A0.9600
C3—H3A0.9700C6—H6B0.9600
C3—H3B0.9700C6—H6C0.9600
O—C41.416 (2)C4—H4A0.9700
O—H0.87 (3)C4—H4B0.9700
C12—C111.494 (2)
C8—N1—N2104.42 (13)H13A—C13—H13B109.5
C5—N2—N1112.34 (13)N4—C13—H13C109.5
C5—N2—C3128.51 (14)H13A—C13—H13C109.5
N1—N2—C3119.15 (13)H13B—C13—H13C109.5
C9—N3—N4104.26 (13)C11—C10—C9105.31 (15)
N1—C8—C7111.36 (14)C11—C10—H10127.3
N1—C8—C9119.42 (14)C9—C10—H10127.3
C7—C8—C9129.22 (15)N4—C11—C10106.54 (14)
C11—N4—N3112.60 (13)N4—C11—C12122.44 (15)
C11—N4—C13128.28 (14)C10—C11—C12131.02 (16)
N3—N4—C13119.10 (14)N2—C5—C7106.63 (14)
N3—C9—C10111.29 (14)N2—C5—C6123.10 (15)
N3—C9—C8119.90 (15)C7—C5—C6130.27 (16)
C10—C9—C8128.80 (15)C5—C7—C8105.25 (15)
N2—C3—C4112.40 (13)C5—C7—H7127.4
N2—C3—H3A109.1C8—C7—H7127.4
C4—C3—H3A109.1C5—C6—H6A109.5
N2—C3—H3B109.1C5—C6—H6B109.5
C4—C3—H3B109.1H6A—C6—H6B109.5
H3A—C3—H3B107.9C5—C6—H6C109.5
C4—O—H108.2 (18)H6A—C6—H6C109.5
C11—C12—H12A109.5H6B—C6—H6C109.5
C11—C12—H12B109.5O—C4—C3109.39 (14)
H12A—C12—H12B109.5O—C4—H4A109.8
C11—C12—H12C109.5C3—C4—H4A109.8
H12A—C12—H12C109.5O—C4—H4B109.8
H12B—C12—H12C109.5C3—C4—H4B109.8
N4—C13—H13A109.5H4A—C4—H4B108.2
N4—C13—H13B109.5
C8—N1—N2—C50.30 (16)N3—N4—C11—C100.32 (17)
C8—N1—N2—C3179.91 (13)C13—N4—C11—C10178.00 (15)
N2—N1—C8—C70.35 (17)N3—N4—C11—C12178.96 (13)
N2—N1—C8—C9179.36 (12)C13—N4—C11—C122.7 (2)
C9—N3—N4—C110.27 (17)C9—C10—C11—N40.23 (17)
C9—N3—N4—C13178.23 (13)C9—C10—C11—C12178.96 (16)
N4—N3—C9—C100.11 (17)N1—N2—C5—C70.13 (17)
N4—N3—C9—C8179.90 (12)C3—N2—C5—C7179.70 (14)
N1—C8—C9—N3179.81 (13)N1—N2—C5—C6179.99 (14)
C7—C8—C9—N30.5 (2)C3—N2—C5—C60.4 (2)
N1—C8—C9—C100.4 (2)N2—C5—C7—C80.08 (17)
C7—C8—C9—C10179.22 (16)C6—C5—C7—C8179.78 (16)
C5—N2—C3—C495.56 (19)N1—C8—C7—C50.28 (18)
N1—N2—C3—C483.98 (17)C9—C8—C7—C5179.39 (15)
N3—C9—C10—C110.08 (18)N2—C3—C4—O65.80 (18)
C8—C9—C10—C11179.70 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O—H···N1i0.87 (3)2.10 (3)2.9441 (19)162 (2)
Symmetry code: (i) x, y+1, z+1.
 

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