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In the title compound, [Li(C15H22BN6)(C5H8N2)]·C5H8N2, the lithium ion shows a LiN4 distorted tetrahedral geometry with a tridentate TpMe2 [TpMe2 = tris­(dimethylpyrazolyl)­borate] ligand and one 3,5-dimethylpyrazole mol­ecule. A clathrated 3,5-dimethylpyrazole mol­ecule appears to be attached to the Li complex through N—H...N, N—H...π and π–π interactions. The crystal packing is otherwise dominated by hydro­phobic methyl–methyl interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014126/ac6105sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014126/ac6105Isup2.hkl
Contains datablock I

CCDC reference: 245147

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.064
  • wR factor = 0.213
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT156_ALERT_4_C Axial System Input Cell not Standard ........... ? PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C23 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C5 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C10 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C14 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C19 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C20 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C25
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 9 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXTL-NT (Bruker, 1998); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

(I) top
Crystal data top
[Li(C15H22BN6)(C5H8N2)]·C5H8N2Z = 2
Mr = 496.40F(000) = 532
Triclinic, P1Dx = 1.135 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5773 (13) ÅCell parameters from 22 reflections
b = 17.629 (3) Åθ = 20.8–37.1°
c = 8.0759 (9) ŵ = 0.07 mm1
α = 90.228 (11)°T = 298 K
β = 102.521 (10)°Prism, colorless
γ = 81.179 (11)°0.60 × 0.40 × 0.20 mm
V = 1452.0 (3) Å3
Data collection top
Rigaku AFC-7S
diffractometer
3500 reflections with I > 2σ(I)
Radiation source: Normal-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ω–2θ scansh = 012
Absorption correction: ψ scan
(North et al., 1968)
k = 2020
Tmin = 0.934, Tmax = 0.989l = 99
5421 measured reflections3 standard reflections every 150 reflections
5115 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.213 w = 1/[σ2(Fo2) + (0.1072P)2 + 0.8283P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5115 reflectionsΔρmax = 0.32 e Å3
335 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (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
xyzUiso*/Ueq
Li10.1848 (5)0.3299 (3)0.4734 (6)0.0497 (11)
B10.1163 (4)0.17631 (19)0.5232 (4)0.0517 (8)
H10.08860.12070.53470.062*
N60.1393 (2)0.21522 (14)0.6979 (3)0.0500 (6)
N40.0031 (2)0.22335 (14)0.3957 (3)0.0512 (6)
N30.0123 (2)0.29597 (14)0.3430 (3)0.0500 (6)
N50.1710 (2)0.28786 (14)0.7083 (3)0.0508 (6)
N70.2700 (2)0.42852 (14)0.5033 (3)0.0530 (6)
N80.3896 (2)0.42013 (15)0.6137 (3)0.0559 (7)
H80.44010.36840.64960.067*
N100.4790 (3)0.22340 (17)0.7928 (4)0.0666 (8)
H100.39600.24100.79150.080*
N90.5481 (3)0.27510 (16)0.7437 (4)0.0670 (8)
N20.2428 (2)0.16728 (14)0.4536 (3)0.0513 (6)
N10.2949 (2)0.23082 (14)0.4197 (3)0.0515 (6)
C230.5506 (3)0.15489 (19)0.8362 (4)0.0600 (8)
C210.6676 (3)0.23667 (19)0.7598 (4)0.0582 (8)
C60.0947 (3)0.31854 (18)0.2223 (4)0.0514 (7)
C180.4229 (3)0.48734 (19)0.6681 (4)0.0549 (8)
C110.1798 (3)0.30738 (19)0.8701 (4)0.0547 (8)
C130.1292 (3)0.1898 (2)0.8513 (4)0.0605 (8)
C170.3228 (3)0.54233 (18)0.5904 (4)0.0593 (8)
H17A0.31760.59510.60220.071*
C160.2302 (3)0.50401 (16)0.4901 (4)0.0510 (7)
C120.1543 (3)0.2474 (2)0.9626 (4)0.0663 (9)
H12A0.15430.24641.07770.080*
C220.6732 (3)0.16213 (19)0.8161 (4)0.0660 (9)
H22A0.74650.12410.83640.079*
C140.2150 (4)0.3831 (2)0.9281 (5)0.0746 (10)
H14C0.22640.41210.83350.112*
H14B0.29520.37541.01310.112*
H14A0.14620.41080.97520.112*
C80.1103 (3)0.2022 (2)0.3072 (4)0.0610 (8)
C70.1738 (3)0.2618 (2)0.1975 (4)0.0662 (9)
H7A0.25410.26390.12140.079*
C200.5497 (4)0.4925 (3)0.7894 (4)0.0789 (11)
H20C0.59740.44180.81890.118*
H20B0.53240.51730.89000.118*
H20A0.60070.52180.73710.118*
C190.1049 (3)0.5375 (2)0.3733 (5)0.0728 (10)
H19C0.06110.49680.32090.109*
H19B0.12310.56900.28740.109*
H19A0.04980.56810.43640.109*
C90.1145 (3)0.3935 (2)0.1300 (4)0.0697 (9)
H9C0.04290.42050.17510.105*
H9B0.19520.42350.14350.105*
H9A0.11820.38510.01160.105*
C240.7736 (4)0.2757 (2)0.7175 (5)0.0806 (11)
H24C0.73850.32800.68210.121*
H24B0.80640.24940.62740.121*
H24A0.84360.27460.81600.121*
C100.1502 (4)0.1258 (2)0.3343 (6)0.0977 (14)
H10C0.08430.09640.42060.147*
H10B0.15960.09850.23030.147*
H10A0.23220.13360.36950.147*
C250.4932 (5)0.0896 (3)0.8882 (6)0.0973 (13)
H25C0.40240.10620.88820.146*
H25B0.53940.07141.00020.146*
H25A0.50060.04880.81000.146*
C150.0945 (5)0.1127 (2)0.8832 (6)0.0962 (14)
H15C0.08310.08510.77970.144*
H15B0.01450.11940.92310.144*
H15A0.16370.08440.96720.144*
C40.4780 (4)0.2596 (2)0.3018 (5)0.0773 (11)
H4C0.44260.31130.32310.116*
H4B0.47540.25470.18270.116*
H4A0.56710.24780.36450.116*
C10.3987 (3)0.20547 (19)0.3562 (4)0.0564 (8)
C20.4144 (4)0.1265 (2)0.3483 (5)0.0727 (10)
H2A0.47990.09510.30880.087*
C30.3146 (4)0.10308 (19)0.4104 (4)0.0656 (9)
C50.2818 (5)0.0246 (2)0.4294 (7)0.1003 (14)
H5C0.20580.02810.47740.150*
H5B0.35450.00670.50280.150*
H5A0.26420.00200.32010.150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.050 (3)0.044 (3)0.057 (3)0.010 (2)0.014 (2)0.003 (2)
B10.059 (2)0.0424 (18)0.057 (2)0.0147 (15)0.0137 (16)0.0044 (15)
N60.0513 (14)0.0546 (15)0.0464 (13)0.0121 (11)0.0133 (11)0.0024 (11)
N40.0506 (14)0.0553 (15)0.0499 (14)0.0159 (11)0.0107 (11)0.0070 (11)
N30.0477 (14)0.0566 (15)0.0465 (13)0.0111 (11)0.0097 (11)0.0044 (11)
N50.0533 (14)0.0575 (15)0.0433 (13)0.0140 (12)0.0107 (11)0.0062 (11)
N70.0470 (14)0.0518 (15)0.0608 (15)0.0110 (11)0.0110 (12)0.0036 (12)
N80.0513 (15)0.0558 (15)0.0614 (16)0.0098 (12)0.0127 (12)0.0043 (12)
N100.0522 (16)0.0715 (19)0.0745 (19)0.0050 (14)0.0137 (14)0.0049 (15)
N90.0573 (17)0.0618 (17)0.0756 (19)0.0044 (14)0.0043 (14)0.0105 (14)
N20.0548 (14)0.0472 (14)0.0513 (14)0.0053 (11)0.0124 (11)0.0052 (11)
N10.0494 (14)0.0551 (15)0.0511 (14)0.0089 (11)0.0128 (11)0.0036 (11)
C230.065 (2)0.062 (2)0.0510 (18)0.0101 (16)0.0085 (15)0.0012 (15)
C210.0566 (19)0.066 (2)0.0479 (17)0.0098 (16)0.0017 (14)0.0018 (14)
C60.0455 (16)0.0665 (19)0.0421 (15)0.0083 (14)0.0102 (13)0.0052 (13)
C180.0588 (19)0.066 (2)0.0487 (17)0.0210 (16)0.0229 (14)0.0062 (14)
C110.0430 (16)0.072 (2)0.0461 (16)0.0010 (14)0.0082 (13)0.0060 (14)
C130.0583 (19)0.072 (2)0.0533 (18)0.0108 (16)0.0160 (15)0.0109 (16)
C170.068 (2)0.0493 (18)0.067 (2)0.0140 (16)0.0271 (17)0.0063 (15)
C160.0533 (17)0.0464 (17)0.0595 (18)0.0072 (13)0.0259 (14)0.0031 (13)
C120.065 (2)0.090 (3)0.0420 (17)0.0058 (18)0.0122 (15)0.0055 (17)
C220.061 (2)0.061 (2)0.070 (2)0.0023 (16)0.0085 (17)0.0027 (16)
C140.076 (2)0.084 (3)0.062 (2)0.015 (2)0.0096 (18)0.0231 (18)
C80.0571 (19)0.072 (2)0.0599 (19)0.0270 (17)0.0130 (15)0.0154 (16)
C70.0509 (18)0.092 (3)0.0541 (19)0.0201 (18)0.0024 (15)0.0076 (18)
C200.068 (2)0.119 (3)0.058 (2)0.035 (2)0.0160 (17)0.016 (2)
C190.061 (2)0.072 (2)0.085 (3)0.0071 (17)0.0153 (18)0.0156 (19)
C90.060 (2)0.084 (3)0.060 (2)0.0054 (18)0.0060 (16)0.0037 (17)
C240.069 (2)0.089 (3)0.087 (3)0.024 (2)0.016 (2)0.001 (2)
C100.089 (3)0.096 (3)0.111 (3)0.053 (3)0.002 (3)0.007 (3)
C250.110 (3)0.091 (3)0.100 (3)0.030 (3)0.032 (3)0.008 (2)
C150.116 (4)0.093 (3)0.089 (3)0.032 (3)0.031 (3)0.029 (2)
C40.060 (2)0.110 (3)0.066 (2)0.012 (2)0.0218 (17)0.002 (2)
C10.0508 (18)0.071 (2)0.0462 (16)0.0024 (15)0.0121 (14)0.0033 (14)
C20.068 (2)0.080 (3)0.067 (2)0.0097 (19)0.0222 (18)0.0106 (18)
C30.075 (2)0.0553 (19)0.062 (2)0.0036 (17)0.0150 (17)0.0101 (15)
C50.124 (4)0.053 (2)0.125 (4)0.000 (2)0.040 (3)0.018 (2)
Geometric parameters (Å, º) top
Li1—N12.045 (5)C12—H12A0.9300
Li1—N72.068 (5)C22—H22A0.9300
Li1—N32.072 (5)C14—H14C0.9600
Li1—N52.081 (5)C14—H14B0.9600
B1—N41.533 (4)C14—H14A0.9600
B1—N21.546 (4)C8—C71.369 (5)
B1—N61.554 (4)C8—C101.502 (5)
B1—H11.0760C7—H7A0.9300
N6—C131.350 (4)C20—H20C0.9600
N6—N51.370 (3)C20—H20B0.9600
N4—C81.361 (4)C20—H20A0.9600
N4—N31.375 (3)C19—H19C0.9600
N3—C61.332 (4)C19—H19B0.9600
N5—C111.338 (4)C19—H19A0.9600
N7—C161.330 (4)C9—H9C0.9600
N7—N81.368 (3)C9—H9B0.9600
N8—C181.333 (4)C9—H9A0.9600
N8—H80.9927C24—H24C0.9600
N10—C231.328 (4)C24—H24B0.9600
N10—N91.363 (4)C24—H24A0.9600
N10—H100.8826C10—H10C0.9600
N9—C211.319 (4)C10—H10B0.9600
N2—C31.352 (4)C10—H10A0.9600
N2—N11.375 (3)C25—H25C0.9600
N1—C11.326 (4)C25—H25B0.9600
C23—C221.366 (5)C25—H25A0.9600
C23—C251.483 (5)C15—H15C0.9600
C21—C221.381 (5)C15—H15B0.9600
C21—C241.501 (5)C15—H15A0.9600
C6—C71.386 (4)C4—C11.489 (5)
C6—C91.484 (5)C4—H4C0.9600
C18—C171.362 (5)C4—H4B0.9600
C18—C201.495 (5)C4—H4A0.9600
C11—C121.389 (5)C1—C21.379 (5)
C11—C141.488 (5)C2—C31.379 (5)
C13—C121.371 (5)C2—H2A0.9300
C13—C151.498 (5)C3—C51.493 (5)
C17—C161.388 (4)C5—H5C0.9600
C17—H17A0.9300C5—H5B0.9600
C16—C191.488 (4)C5—H5A0.9600
N1—Li1—N7118.1 (2)C11—C14—H14A109.5
N1—Li1—N392.1 (2)H14C—C14—H14A109.5
N7—Li1—N3138.3 (3)H14B—C14—H14A109.5
N1—Li1—N593.7 (2)N4—C8—C7107.4 (3)
N7—Li1—N5110.1 (2)N4—C8—C10122.9 (3)
N3—Li1—N594.7 (2)C7—C8—C10129.6 (3)
N4—B1—N2109.8 (2)C8—C7—C6106.4 (3)
N4—B1—N6110.9 (2)C8—C7—H7A126.8
N2—B1—N6109.9 (2)C6—C7—H7A126.8
N4—B1—H1106.2C18—C20—H20C109.5
N2—B1—H1109.2C18—C20—H20B109.5
N6—B1—H1110.7H20C—C20—H20B109.5
C13—N6—N5110.3 (2)C18—C20—H20A109.5
C13—N6—B1130.2 (3)H20C—C20—H20A109.5
N5—N6—B1119.5 (2)H20B—C20—H20A109.5
C8—N4—N3109.5 (2)C16—C19—H19C109.5
C8—N4—B1129.5 (3)C16—C19—H19B109.5
N3—N4—B1120.8 (2)H19C—C19—H19B109.5
C6—N3—N4106.5 (2)C16—C19—H19A109.5
C6—N3—Li1142.9 (2)H19C—C19—H19A109.5
N4—N3—Li1110.6 (2)H19B—C19—H19A109.5
C11—N5—N6106.3 (2)C6—C9—H9C109.5
C11—N5—Li1142.1 (3)C6—C9—H9B109.5
N6—N5—Li1111.6 (2)H9C—C9—H9B109.5
C16—N7—N8104.3 (2)C6—C9—H9A109.5
C16—N7—Li1137.4 (2)H9C—C9—H9A109.5
N8—N7—Li1114.4 (2)H9B—C9—H9A109.5
C18—N8—N7112.3 (3)C21—C24—H24C109.5
C18—N8—H8126.6C21—C24—H24B109.5
N7—N8—H8121.1H24C—C24—H24B109.5
C23—N10—N9113.1 (3)C21—C24—H24A109.5
C23—N10—H10131.6H24C—C24—H24A109.5
N9—N10—H10115.4H24B—C24—H24A109.5
C21—N9—N10104.2 (3)C8—C10—H10C109.5
C3—N2—N1109.9 (3)C8—C10—H10B109.5
C3—N2—B1129.6 (3)H10C—C10—H10B109.5
N1—N2—B1120.5 (2)C8—C10—H10A109.5
C1—N1—N2106.7 (2)H10C—C10—H10A109.5
C1—N1—Li1141.9 (3)H10B—C10—H10A109.5
N2—N1—Li1111.3 (2)C23—C25—H25C109.5
N10—C23—C22105.1 (3)C23—C25—H25B109.5
N10—C23—C25121.8 (3)H25C—C25—H25B109.5
C22—C23—C25133.1 (3)C23—C25—H25A109.5
N9—C21—C22110.6 (3)H25C—C25—H25A109.5
N9—C21—C24119.8 (3)H25B—C25—H25A109.5
C22—C21—C24129.6 (3)C13—C15—H15C109.5
N3—C6—C7110.2 (3)C13—C15—H15B109.5
N3—C6—C9121.3 (3)H15C—C15—H15B109.5
C7—C6—C9128.5 (3)C13—C15—H15A109.5
N8—C18—C17106.3 (3)H15C—C15—H15A109.5
N8—C18—C20121.9 (3)H15B—C15—H15A109.5
C17—C18—C20131.8 (3)C1—C4—H4C109.5
N5—C11—C12109.6 (3)C1—C4—H4B109.5
N5—C11—C14120.9 (3)H4C—C4—H4B109.5
C12—C11—C14129.5 (3)C1—C4—H4A109.5
N6—C13—C12107.0 (3)H4C—C4—H4A109.5
N6—C13—C15123.8 (3)H4B—C4—H4A109.5
C12—C13—C15129.1 (3)N1—C1—C2109.9 (3)
C18—C17—C16106.5 (3)N1—C1—C4121.2 (3)
C18—C17—H17A126.8C2—C1—C4128.9 (3)
C16—C17—H17A126.8C3—C2—C1106.9 (3)
N7—C16—C17110.6 (3)C3—C2—H2A126.6
N7—C16—C19121.1 (3)C1—C2—H2A126.6
C17—C16—C19128.2 (3)N2—C3—C2106.7 (3)
C13—C12—C11106.7 (3)N2—C3—C5122.9 (3)
C13—C12—H12A126.6C2—C3—C5130.5 (3)
C11—C12—H12A126.6C3—C5—H5C109.5
C23—C22—C21107.0 (3)C3—C5—H5B109.5
C23—C22—H22A126.5H5C—C5—H5B109.5
C21—C22—H22A126.5C3—C5—H5A109.5
C11—C14—H14C109.5H5C—C5—H5A109.5
C11—C14—H14B109.5H5B—C5—H5A109.5
H14C—C14—H14B109.5
 

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