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The crystal structure of the title compound, [Cu3(C9H7N2)3], consists of discrete CuI–phenyl­pyrazolyl trimers, with Cu atoms bridged by exo-bidentate phenyl­pyrazolyl ligands having short intra­molecular Cu...Cu contacts [3.2076 (14)–3.2402 (14) Å]. The Cu3N6 nine-membered rings are essentially planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020708/lh2093sup1.cif
Contains datablocks II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020708/lh2093IIsup2.hkl
Contains datablock II

CCDC reference: 614871

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.055
  • wR factor = 0.131
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 141.00 A   3
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.793 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.94 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

cyclo-Tris(µ2-3-phenyl-1H-pyrazole)tricopper(I) top
Crystal data top
[Cu3(C9H7N2)3]Dx = 1.620 Mg m3
Mr = 620.12Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4/nCell parameters from 6575 reflections
Hall symbol: -P 4aθ = 2.3–24.8°
a = 26.6249 (19) ŵ = 2.51 mm1
c = 7.1739 (7) ÅT = 173 K
V = 5085.5 (7) Å3Needle, colourless
Z = 80.19 × 0.09 × 0.08 mm
F(000) = 2496
Data collection top
Stoe IPDS-II two-circle
diffractometer
4701 independent reflections
Radiation source: fine-focus sealed tube2005 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.090
ω scansθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 3232
Tmin = 0.647, Tmax = 0.824k = 3232
29854 measured reflectionsl = 87
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 0.79 w = 1/[σ2(Fo2) + (0.0458P)2]
where P = (Fo2 + 2Fc2)/3
4701 reflections(Δ/σ)max < 0.001
325 parametersΔρmax = 1.93 e Å3
0 restraintsΔρmin = 0.66 e Å3
Special details top

Experimental. ;

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
Cu10.56636 (4)0.46194 (4)0.32062 (15)0.0294 (3)
Cu20.48996 (4)0.55369 (4)0.23322 (16)0.0312 (3)
Cu30.45712 (4)0.43990 (4)0.15080 (15)0.0306 (3)
N10.5036 (3)0.3886 (3)0.1711 (11)0.0325 (17)
N20.5509 (2)0.3971 (2)0.2450 (10)0.0291 (17)
C30.5780 (3)0.3549 (3)0.2229 (13)0.028 (2)
C40.5491 (3)0.3183 (3)0.1346 (14)0.034 (2)
H40.55850.28500.10270.041*
C50.5028 (4)0.3421 (3)0.1038 (14)0.037 (2)
H50.47490.32700.04330.044*
N110.5825 (2)0.5272 (3)0.3869 (10)0.0274 (17)
N120.5511 (2)0.5668 (2)0.3507 (10)0.0267 (16)
C130.5724 (3)0.6095 (3)0.4118 (12)0.028 (2)
C140.6184 (3)0.5973 (3)0.4912 (12)0.027 (2)
H140.64160.62000.54680.032*
C150.6239 (3)0.5462 (3)0.4740 (12)0.026 (2)
H150.65190.52720.51580.032*
N210.4263 (3)0.5411 (3)0.1434 (10)0.0305 (17)
N220.4102 (2)0.4914 (3)0.1236 (10)0.0276 (17)
C230.3600 (3)0.4913 (3)0.0924 (13)0.029 (2)
C240.3429 (3)0.5409 (3)0.0878 (13)0.034 (2)
H240.30960.55230.06510.041*
C250.3850 (3)0.5699 (3)0.1236 (12)0.031 (2)
H250.38480.60550.13290.037*
C310.6312 (3)0.3510 (3)0.2823 (13)0.031 (2)
C320.6643 (3)0.3209 (3)0.1812 (14)0.037 (2)
H320.65280.30310.07470.044*
C330.7146 (4)0.3171 (3)0.2375 (17)0.050 (3)
H330.73710.29640.16920.060*
C340.7320 (4)0.3432 (3)0.3911 (16)0.048 (3)
H340.76580.34000.43080.057*
C350.6987 (4)0.3743 (4)0.4864 (15)0.044 (3)
H350.71040.39310.59000.052*
C360.6495 (3)0.3782 (3)0.4340 (14)0.036 (2)
H360.62760.39970.50150.043*
C410.5479 (3)0.6582 (3)0.3860 (11)0.0221 (19)
C420.5768 (3)0.7012 (3)0.3579 (13)0.033 (2)
H420.61230.69880.36310.040*
C430.5546 (4)0.7476 (3)0.3225 (13)0.041 (2)
H430.57500.77620.30070.049*
C440.5029 (4)0.7518 (3)0.3190 (14)0.043 (3)
H440.48750.78330.29370.052*
C450.4735 (3)0.7094 (3)0.3530 (13)0.038 (2)
H450.43790.71200.35330.045*
C460.4963 (3)0.6637 (3)0.3864 (13)0.030 (2)
H460.47590.63510.41030.036*
C510.3323 (3)0.4446 (3)0.0778 (12)0.026 (2)
C520.2846 (3)0.4408 (3)0.1607 (13)0.032 (2)
H520.26950.46960.21550.038*
C530.2595 (3)0.3952 (4)0.1627 (15)0.043 (2)
H530.22750.39280.22090.051*
C540.2804 (3)0.3532 (4)0.0812 (14)0.043 (3)
H540.26280.32220.08020.052*
C550.3278 (4)0.3571 (4)0.0003 (13)0.038 (2)
H550.34300.32810.05270.045*
C560.3528 (3)0.4016 (4)0.0039 (12)0.030 (2)
H560.38460.40350.06330.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0327 (6)0.0252 (6)0.0304 (6)0.0013 (5)0.0015 (5)0.0003 (5)
Cu20.0265 (6)0.0322 (6)0.0349 (7)0.0030 (5)0.0035 (5)0.0030 (5)
Cu30.0260 (6)0.0349 (6)0.0310 (6)0.0016 (5)0.0014 (5)0.0042 (6)
N10.030 (4)0.035 (4)0.033 (5)0.001 (3)0.002 (4)0.004 (4)
N20.030 (4)0.028 (4)0.029 (4)0.000 (3)0.002 (4)0.006 (3)
C30.027 (5)0.029 (5)0.029 (6)0.002 (4)0.003 (4)0.001 (4)
C40.045 (6)0.020 (4)0.038 (6)0.001 (4)0.002 (5)0.004 (4)
C50.048 (6)0.030 (5)0.034 (6)0.000 (5)0.004 (5)0.004 (4)
N110.027 (4)0.034 (4)0.021 (4)0.000 (3)0.001 (3)0.001 (3)
N120.028 (4)0.027 (4)0.025 (4)0.004 (3)0.002 (3)0.003 (4)
C130.028 (5)0.027 (5)0.027 (5)0.008 (4)0.008 (4)0.001 (4)
C140.025 (5)0.032 (5)0.023 (5)0.009 (4)0.000 (4)0.005 (4)
C150.023 (5)0.034 (5)0.022 (5)0.007 (4)0.000 (4)0.008 (4)
N210.032 (4)0.029 (4)0.030 (5)0.007 (4)0.001 (4)0.008 (4)
N220.025 (4)0.037 (4)0.021 (5)0.000 (3)0.006 (3)0.003 (3)
C230.028 (5)0.030 (5)0.030 (6)0.004 (4)0.002 (4)0.004 (4)
C240.023 (5)0.044 (6)0.036 (6)0.002 (4)0.004 (4)0.000 (5)
C250.036 (5)0.031 (5)0.026 (6)0.004 (4)0.000 (4)0.007 (4)
C310.034 (5)0.024 (5)0.036 (6)0.005 (4)0.006 (4)0.010 (4)
C320.037 (5)0.032 (5)0.041 (6)0.005 (4)0.006 (5)0.001 (5)
C330.038 (6)0.032 (5)0.079 (9)0.012 (4)0.019 (6)0.001 (6)
C340.038 (6)0.037 (6)0.068 (8)0.003 (5)0.009 (6)0.002 (6)
C350.037 (6)0.036 (6)0.058 (8)0.004 (5)0.011 (5)0.005 (5)
C360.035 (6)0.032 (5)0.040 (6)0.012 (4)0.004 (5)0.001 (5)
C410.028 (5)0.022 (4)0.017 (5)0.000 (4)0.005 (4)0.000 (4)
C420.030 (5)0.029 (5)0.041 (6)0.005 (4)0.001 (5)0.010 (4)
C430.057 (6)0.033 (5)0.033 (6)0.007 (5)0.004 (5)0.000 (5)
C440.056 (7)0.030 (5)0.042 (7)0.010 (5)0.005 (5)0.003 (5)
C450.039 (5)0.041 (6)0.033 (6)0.002 (5)0.007 (5)0.009 (5)
C460.029 (5)0.027 (5)0.033 (6)0.003 (4)0.002 (4)0.000 (4)
C510.021 (5)0.035 (5)0.022 (5)0.006 (4)0.001 (4)0.003 (4)
C520.020 (4)0.041 (5)0.034 (6)0.005 (4)0.004 (4)0.002 (5)
C530.034 (5)0.053 (6)0.041 (6)0.002 (5)0.007 (5)0.005 (5)
C540.032 (6)0.055 (7)0.043 (6)0.002 (5)0.005 (5)0.008 (5)
C550.040 (6)0.035 (6)0.039 (6)0.009 (5)0.001 (5)0.005 (4)
C560.022 (5)0.046 (6)0.023 (6)0.001 (5)0.002 (4)0.001 (4)
Geometric parameters (Å, º) top
Cu1—N111.852 (7)C32—C331.404 (12)
Cu1—N21.857 (7)C32—H320.9500
Cu2—N211.845 (7)C33—C341.381 (14)
Cu2—N121.867 (7)C33—H330.9500
Cu3—N11.849 (7)C34—C351.391 (14)
Cu3—N221.864 (7)C34—H340.9500
N1—C51.330 (11)C35—C361.367 (12)
N1—N21.384 (9)C35—H350.9500
N2—C31.345 (10)C36—H360.9500
C3—C41.395 (11)C41—C461.381 (11)
C3—C311.482 (11)C41—C421.394 (11)
C4—C51.402 (12)C42—C431.392 (12)
C4—H40.9500C42—H420.9500
C5—H50.9500C43—C441.382 (12)
N11—C151.363 (11)C43—H430.9500
N11—N121.370 (9)C44—C451.395 (12)
N12—C131.343 (10)C44—H440.9500
C13—C141.388 (12)C45—C461.381 (12)
C13—C411.463 (11)C45—H450.9500
C14—C151.376 (12)C46—H460.9500
C14—H140.9500C51—C561.397 (11)
C15—H150.9500C51—C521.407 (11)
N21—C251.348 (10)C52—C531.387 (12)
N21—N221.398 (9)C52—H520.9500
N22—C231.356 (10)C53—C541.379 (13)
C23—C241.399 (12)C53—H530.9500
C23—C511.448 (11)C54—C551.394 (13)
C24—C251.386 (11)C54—H540.9500
C24—H240.9500C55—C561.359 (13)
C25—H250.9500C55—H550.9500
C31—C321.394 (11)C56—H560.9500
C31—C361.395 (12)
N11—Cu1—N2177.8 (3)C31—C32—C33119.7 (9)
N21—Cu2—N12173.6 (3)C31—C32—H32120.2
N1—Cu3—N22178.5 (3)C33—C32—H32120.2
C5—N1—N2107.7 (7)C34—C33—C32120.8 (9)
C5—N1—Cu3130.5 (6)C34—C33—H33119.6
N2—N1—Cu3121.2 (5)C32—C33—H33119.6
C3—N2—N1107.9 (7)C33—C34—C35118.6 (9)
C3—N2—Cu1133.8 (6)C33—C34—H34120.7
N1—N2—Cu1117.7 (5)C35—C34—H34120.7
N2—C3—C4109.8 (7)C36—C35—C34121.4 (10)
N2—C3—C31122.5 (7)C36—C35—H35119.3
C4—C3—C31127.6 (8)C34—C35—H35119.3
C3—C4—C5104.0 (7)C35—C36—C31120.6 (9)
C3—C4—H4128.0C35—C36—H36119.7
C5—C4—H4128.0C31—C36—H36119.7
N1—C5—C4110.5 (8)C46—C41—C42117.5 (7)
N1—C5—H5124.8C46—C41—C13122.6 (7)
C4—C5—H5124.8C42—C41—C13120.0 (7)
C15—N11—N12107.1 (6)C43—C42—C41121.5 (8)
C15—N11—Cu1130.7 (6)C43—C42—H42119.3
N12—N11—Cu1122.2 (5)C41—C42—H42119.3
C13—N12—N11109.4 (6)C44—C43—C42119.9 (9)
C13—N12—Cu2132.4 (6)C44—C43—H43120.1
N11—N12—Cu2118.2 (5)C42—C43—H43120.1
N12—C13—C14108.0 (7)C43—C44—C45119.3 (8)
N12—C13—C41121.3 (7)C43—C44—H44120.4
C14—C13—C41130.7 (8)C45—C44—H44120.4
C15—C14—C13106.7 (8)C46—C45—C44119.8 (8)
C15—C14—H14126.7C46—C45—H45120.1
C13—C14—H14126.7C44—C45—H45120.1
N11—C15—C14108.8 (7)C41—C46—C45122.0 (8)
N11—C15—H15125.6C41—C46—H46119.0
C14—C15—H15125.6C45—C46—H46119.0
C25—N21—N22106.2 (6)C56—C51—C52118.0 (8)
C25—N21—Cu2133.0 (6)C56—C51—C23122.4 (8)
N22—N21—Cu2119.2 (5)C52—C51—C23119.5 (7)
C23—N22—N21108.7 (6)C53—C52—C51120.2 (8)
C23—N22—Cu3132.6 (6)C53—C52—H52119.9
N21—N22—Cu3118.7 (5)C51—C52—H52119.9
N22—C23—C24108.9 (7)C54—C53—C52120.7 (9)
N22—C23—C51121.1 (7)C54—C53—H53119.6
C24—C23—C51130.0 (8)C52—C53—H53119.6
C25—C24—C23105.0 (8)C53—C54—C55118.8 (9)
C25—C24—H24127.5C53—C54—H54120.6
C23—C24—H24127.5C55—C54—H54120.6
N21—C25—C24111.2 (8)C56—C55—C54121.1 (9)
N21—C25—H25124.4C56—C55—H55119.4
C24—C25—H25124.4C54—C55—H55119.4
C32—C31—C36118.9 (8)C55—C56—C51121.1 (8)
C32—C31—C3119.6 (8)C55—C56—H56119.5
C36—C31—C3121.5 (8)C51—C56—H56119.5
C5—N1—N2—C30.7 (10)C23—C24—C25—N211.9 (11)
Cu3—N1—N2—C3173.2 (6)N2—C3—C31—C32147.0 (8)
C5—N1—N2—Cu1171.8 (6)C4—C3—C31—C3231.2 (13)
Cu3—N1—N2—Cu10.7 (9)N2—C3—C31—C3630.7 (13)
N1—N2—C3—C40.0 (10)C4—C3—C31—C36151.1 (9)
Cu1—N2—C3—C4170.8 (7)C36—C31—C32—C332.4 (13)
N1—N2—C3—C31178.5 (8)C3—C31—C32—C33179.9 (8)
Cu1—N2—C3—C317.7 (13)C31—C32—C33—C340.6 (14)
N2—C3—C4—C50.7 (10)C32—C33—C34—C351.5 (15)
C31—C3—C4—C5177.7 (9)C33—C34—C35—C361.8 (15)
N2—N1—C5—C41.2 (10)C34—C35—C36—C310.0 (14)
Cu3—N1—C5—C4172.7 (7)C32—C31—C36—C352.1 (13)
C3—C4—C5—N11.2 (10)C3—C31—C36—C35179.8 (8)
C15—N11—N12—C130.5 (9)N12—C13—C41—C4632.3 (13)
Cu1—N11—N12—C13179.4 (6)C14—C13—C41—C46149.3 (9)
C15—N11—N12—Cu2179.3 (5)N12—C13—C41—C42147.0 (8)
Cu1—N11—N12—Cu20.8 (8)C14—C13—C41—C4231.3 (14)
N11—N12—C13—C140.6 (9)C46—C41—C42—C433.1 (13)
Cu2—N12—C13—C14179.2 (6)C13—C41—C42—C43176.3 (8)
N11—N12—C13—C41178.1 (7)C41—C42—C43—C441.6 (14)
Cu2—N12—C13—C412.1 (12)C42—C43—C44—C450.6 (15)
N12—C13—C14—C150.5 (9)C43—C44—C45—C461.2 (15)
C41—C13—C14—C15178.0 (8)C42—C41—C46—C452.5 (13)
N12—N11—C15—C140.2 (9)C13—C41—C46—C45176.8 (8)
Cu1—N11—C15—C14179.7 (6)C44—C45—C46—C410.5 (14)
C13—C14—C15—N110.2 (10)N22—C23—C51—C5635.5 (13)
C25—N21—N22—C230.0 (9)C24—C23—C51—C56147.9 (10)
Cu2—N21—N22—C23167.9 (6)N22—C23—C51—C52139.6 (9)
C25—N21—N22—Cu3177.9 (6)C24—C23—C51—C5237.1 (15)
Cu2—N21—N22—Cu310.0 (8)C56—C51—C52—C531.1 (13)
N21—N22—C23—C241.2 (10)C23—C51—C52—C53174.2 (8)
Cu3—N22—C23—C24178.7 (6)C51—C52—C53—C541.1 (14)
N21—N22—C23—C51176.1 (7)C52—C53—C54—C551.5 (15)
Cu3—N22—C23—C511.4 (14)C53—C54—C55—C562.0 (14)
N22—C23—C24—C251.9 (11)C54—C55—C56—C512.0 (13)
C51—C23—C24—C25175.1 (9)C52—C51—C56—C551.5 (13)
N22—N21—C25—C241.2 (9)C23—C51—C56—C55173.6 (8)
Cu2—N21—C25—C24166.7 (7)
 

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