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The title compound, [ReCl(C10H11NO2)2(CO)3]·CHCl3, has Re—N distances of 2.202 (8) and 2.237 (7) Å, an N—Re—N angle of 84.1 (3)° and 2-hydr­oxy-4-oxopent-2-en-3-yl (acacH) units which are uncoordinated. The acacH units are in the enol tautomeric form, with delocalized single and double bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016996/tk2147sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016996/tk2147Isup2.hkl
Contains datablock I

CCDC reference: 647458

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.014 Å
  • R factor = 0.058
  • wR factor = 0.151
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT355_ALERT_3_A Long O-H Bond (0.82A) O5 - H5O ... 1.13 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.308 0.907 Tmin and Tmax expected: 0.276 0.915 RR = 1.127 Please check that your absorption correction is appropriate. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.13 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.73 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Re1 - C1 .. 5.80 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C1S PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O4 PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O6 PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14 PLAT355_ALERT_3_C Long O-H Bond (0.82A) O7 - H7O ... 1.06 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 35.00 A   3
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 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 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

fac-tricarbonylchloridobis[3-(4-pyridyl)pentane-2,4-dione-κN]rhenium(I) chloroform solvate top
Crystal data top
[ReCl(C10H11NO2)2(CO)3]·CHCl3F(000) = 1520
Mr = 779.44Dx = 1.726 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8612 reflections
a = 10.889 (4) Åθ = 2.5–26.0°
b = 11.607 (4) ŵ = 4.45 mm1
c = 24.306 (10) ÅT = 110 K
β = 102.477 (14)°Plate, colorless
V = 3000 (2) Å30.30 × 0.25 × 0.02 mm
Z = 4
Data collection top
Nonius KappaCCD (with Oxford Cryostream)
diffractometer
5749 independent reflections
Radiation source: fine-focus sealed tube4148 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
ω scans with κ offsetsθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
h = 1313
Tmin = 0.308, Tmax = 0.907k = 1414
27300 measured reflectionsl = 2929
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.37 w = 1/[σ2(Fo2) + (0.0586P)2 + 2.57P]
where P = (Fo2 + 2Fc2)/3
5749 reflections(Δ/σ)max = 0.008
353 parametersΔρmax = 1.97 e Å3
0 restraintsΔρmin = 1.80 e Å3
Special details top

Experimental. 1H NMR (250 MHz, acetone-d6): 17.08 (s, 2H), 8.84 (d, 4H, J = 6.2), 7.54 (d, 4H, J = 6.3), 1.95 (s, 12H).

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
Re10.38042 (4)0.62880 (3)0.297709 (14)0.03423 (15)
Cl10.4886 (3)0.81552 (19)0.31775 (9)0.0452 (6)
O10.2549 (7)0.3933 (6)0.2683 (3)0.0484 (18)
O20.3017 (8)0.6311 (5)0.4118 (3)0.056 (2)
O30.1247 (8)0.7359 (7)0.2449 (3)0.068 (2)
O40.6907 (7)0.5455 (5)0.0010 (3)0.0473 (18)
O50.6508 (7)0.7541 (6)0.0046 (3)0.0433 (17)
H5O0.672 (10)0.664 (9)0.018 (4)0.065*
O61.1297 (8)0.3703 (7)0.4053 (4)0.073 (2)
O71.0437 (9)0.2884 (8)0.4836 (3)0.074 (2)
H7O1.102 (14)0.338 (12)0.463 (6)0.111*
N10.4579 (8)0.6302 (6)0.2197 (3)0.0355 (18)
N20.5625 (7)0.5502 (6)0.3366 (3)0.0340 (18)
C10.3013 (10)0.4786 (10)0.2791 (4)0.043 (3)
C20.3286 (12)0.6298 (7)0.3675 (4)0.051 (3)
C30.2215 (11)0.6978 (8)0.2652 (4)0.046 (3)
C40.5719 (10)0.6674 (7)0.2197 (4)0.036 (2)
H40.62310.69320.25430.044*
C50.6212 (10)0.6707 (8)0.1712 (4)0.039 (2)
H50.70440.69750.17320.046*
C60.5483 (9)0.6350 (7)0.1206 (3)0.033 (2)
C70.4262 (10)0.6003 (7)0.1203 (3)0.035 (2)
H70.37190.57800.08590.042*
C80.3833 (9)0.5982 (7)0.1699 (3)0.034 (2)
H80.29960.57380.16900.041*
C90.6380 (11)0.4245 (8)0.0714 (4)0.048 (3)
H9A0.65020.36500.04450.072*
H9B0.55610.41350.08120.072*
H9C0.70480.41860.10550.072*
C100.6423 (10)0.5410 (8)0.0455 (4)0.040 (2)
C110.5980 (9)0.6418 (7)0.0673 (3)0.033 (2)
C120.6035 (9)0.7476 (7)0.0401 (3)0.034 (2)
C130.5524 (10)0.8569 (7)0.0582 (4)0.045 (2)
H13A0.61920.91500.06580.067*
H13B0.52100.84310.09250.067*
H13C0.48350.88450.02820.067*
C140.6049 (9)0.4565 (7)0.3144 (4)0.034 (2)
H140.55460.42390.28120.041*
C150.7192 (10)0.4050 (8)0.3379 (4)0.039 (2)
H150.74640.33990.32010.046*
C160.7928 (9)0.4468 (9)0.3863 (4)0.040 (2)
C170.7474 (11)0.5455 (8)0.4109 (4)0.046 (3)
H170.79490.57810.44470.055*
C180.6338 (10)0.5924 (8)0.3848 (4)0.040 (2)
H180.60400.65780.40150.047*
C191.0096 (12)0.4825 (12)0.3309 (5)0.083 (4)
H19A1.08530.52940.33320.124*
H19B0.93570.53280.32570.124*
H19C1.00050.42930.29900.124*
C201.0203 (12)0.4164 (11)0.3833 (5)0.064 (3)
C210.9210 (11)0.3978 (8)0.4121 (4)0.045 (3)
C220.9372 (11)0.3346 (11)0.4607 (5)0.059 (3)
C230.8322 (13)0.3104 (16)0.4899 (5)0.102 (5)
H23A0.83650.22980.50220.153*
H23B0.75140.32450.46380.153*
H23C0.83990.36090.52270.153*
Cl1S0.2166 (4)0.3560 (3)0.11919 (15)0.0815 (10)
Cl2S0.0285 (5)0.3272 (5)0.1385 (2)0.1329 (18)
Cl3S0.0342 (6)0.5336 (5)0.0859 (3)0.170 (2)
C1S0.0705 (17)0.3922 (13)0.0883 (6)0.113 (7)
H1S0.04610.35690.04990.135*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.0497 (3)0.0274 (2)0.0299 (2)0.00554 (18)0.01803 (16)0.00292 (15)
Cl10.075 (2)0.0287 (12)0.0353 (12)0.0014 (12)0.0183 (12)0.0000 (9)
O10.051 (5)0.039 (4)0.057 (4)0.001 (4)0.016 (4)0.002 (3)
O20.095 (7)0.042 (4)0.048 (4)0.012 (4)0.051 (4)0.011 (3)
O30.064 (6)0.065 (5)0.081 (6)0.024 (5)0.030 (5)0.033 (4)
O40.073 (6)0.039 (4)0.038 (3)0.001 (3)0.030 (4)0.005 (3)
O50.057 (5)0.041 (4)0.036 (3)0.003 (3)0.019 (3)0.008 (3)
O60.045 (6)0.083 (6)0.093 (6)0.005 (5)0.014 (5)0.007 (5)
O70.066 (7)0.088 (7)0.064 (5)0.012 (5)0.007 (5)0.008 (4)
N10.054 (5)0.025 (4)0.034 (4)0.005 (4)0.023 (4)0.005 (3)
N20.047 (5)0.031 (4)0.026 (4)0.003 (4)0.012 (3)0.000 (3)
C10.046 (7)0.054 (7)0.036 (5)0.022 (5)0.021 (5)0.018 (5)
C20.090 (9)0.020 (5)0.048 (6)0.015 (5)0.028 (6)0.001 (4)
C30.052 (8)0.038 (6)0.057 (6)0.010 (5)0.029 (6)0.019 (5)
C40.055 (7)0.029 (5)0.030 (5)0.006 (4)0.019 (5)0.004 (4)
C50.051 (7)0.035 (5)0.033 (5)0.016 (4)0.016 (5)0.005 (4)
C60.050 (6)0.023 (4)0.027 (4)0.005 (4)0.012 (4)0.002 (3)
C70.052 (7)0.028 (5)0.025 (4)0.004 (4)0.007 (4)0.001 (3)
C80.036 (6)0.037 (5)0.029 (4)0.004 (4)0.009 (4)0.003 (4)
C90.071 (8)0.039 (5)0.043 (6)0.009 (5)0.029 (5)0.004 (4)
C100.055 (7)0.039 (5)0.030 (5)0.003 (5)0.017 (5)0.003 (4)
C110.046 (6)0.027 (5)0.028 (4)0.002 (4)0.013 (4)0.002 (3)
C120.037 (6)0.035 (5)0.031 (5)0.004 (4)0.008 (4)0.002 (4)
C130.057 (7)0.031 (5)0.048 (6)0.001 (5)0.015 (5)0.002 (4)
C140.040 (6)0.028 (5)0.035 (5)0.000 (4)0.009 (4)0.010 (4)
C150.044 (7)0.041 (5)0.032 (5)0.000 (4)0.012 (4)0.010 (4)
C160.030 (6)0.056 (6)0.035 (5)0.006 (5)0.008 (4)0.007 (4)
C170.068 (8)0.038 (6)0.034 (5)0.006 (5)0.014 (5)0.010 (4)
C180.055 (7)0.033 (5)0.033 (5)0.005 (5)0.015 (5)0.002 (4)
C190.052 (9)0.122 (12)0.080 (9)0.011 (8)0.025 (7)0.028 (8)
C200.049 (9)0.061 (7)0.076 (8)0.006 (6)0.001 (7)0.004 (6)
C210.054 (7)0.044 (6)0.041 (6)0.003 (5)0.016 (5)0.005 (4)
C220.042 (8)0.082 (8)0.050 (7)0.017 (6)0.006 (5)0.010 (6)
C230.060 (10)0.192 (16)0.060 (8)0.003 (10)0.026 (7)0.049 (10)
Cl1S0.096 (3)0.073 (2)0.078 (2)0.0042 (19)0.027 (2)0.0085 (17)
Cl2S0.102 (4)0.188 (5)0.118 (4)0.034 (4)0.044 (3)0.011 (4)
Cl3S0.131 (5)0.118 (4)0.236 (7)0.015 (4)0.018 (5)0.037 (4)
C1S0.120 (15)0.099 (12)0.084 (10)0.041 (10)0.053 (10)0.032 (9)
Geometric parameters (Å, º) top
Re1—Cl12.465 (2)C9—H9C0.9800
Re1—N12.237 (7)C10—C111.412 (12)
Re1—N22.202 (8)C11—C121.402 (11)
Re1—C11.954 (12)C12—C131.489 (12)
Re1—C21.901 (10)C13—H13A0.9800
Re1—C31.915 (12)C13—H13B0.9800
O1—C11.117 (12)C13—H13C0.9800
O2—C21.174 (11)C14—C151.388 (13)
O3—C31.151 (12)C14—H140.9500
C10—O41.302 (10)C15—C161.362 (13)
C12—O51.301 (10)C15—H150.9500
O5—H5O1.13 (11)C16—C171.428 (13)
C20—O61.309 (14)C16—C211.512 (14)
C22—O71.290 (13)C17—C181.375 (14)
O7—H7O1.06 (15)C17—H170.9500
N1—C41.315 (12)C18—H180.9500
N1—C81.355 (11)C19—C201.470 (16)
N2—C141.340 (10)C19—H19A0.9800
N2—C181.349 (11)C19—H19B0.9800
C4—C51.398 (12)C19—H19C0.9800
C4—H40.9500C20—C211.426 (15)
C5—C61.375 (12)C21—C221.369 (14)
C5—H50.9500C22—C231.496 (16)
C6—C71.388 (13)C23—H23A0.9800
C6—C111.511 (11)C23—H23B0.9800
C7—C81.385 (11)C23—H23C0.9800
C7—H70.9500Cl1S—C1S1.660 (16)
C8—H80.9500Cl2S—C1S1.95 (2)
C9—C101.498 (12)Cl3S—C1S1.687 (14)
C9—H9A0.9800C1S—H1S1.0000
C9—H9B0.9800
Cl1—Re1—N286.08 (19)C12—C11—C6120.6 (7)
Cl1—Re1—N184.81 (19)C10—C11—C6119.6 (7)
C2—Re1—C387.1 (4)O5—C12—C11120.6 (8)
C2—Re1—C190.6 (4)O5—C12—C13116.0 (8)
C3—Re1—C187.9 (4)C11—C12—C13123.4 (8)
C2—Re1—N291.8 (4)C12—C13—H13A109.5
C3—Re1—N2178.9 (3)C12—C13—H13B109.5
C1—Re1—N292.4 (3)H13A—C13—H13B109.5
C2—Re1—N1175.2 (4)C12—C13—H13C109.5
C3—Re1—N196.9 (3)H13A—C13—H13C109.5
C1—Re1—N192.2 (3)H13B—C13—H13C109.5
N1—Re1—N284.1 (3)N2—C14—C15122.7 (8)
C2—Re1—Cl192.3 (3)N2—C14—H14118.7
C3—Re1—Cl193.7 (3)C15—C14—H14118.7
C1—Re1—Cl1176.8 (3)C16—C15—C14120.7 (8)
C10—O4—H5O104 (4)C16—C15—H15119.6
C12—O5—H5O109 (5)C14—C15—H15119.6
C20—O6—H7O98 (6)C15—C16—C17117.0 (9)
C22—O7—H7O99 (8)C15—C16—C21122.9 (9)
C4—N1—C8118.4 (7)C17—C16—C21120.0 (9)
C4—N1—Re1122.0 (6)C18—C17—C16118.9 (9)
C8—N1—Re1119.5 (6)C18—C17—H17120.6
C14—N2—C18117.4 (8)C16—C17—H17120.6
C14—N2—Re1121.3 (6)N2—C18—C17123.2 (8)
C18—N2—Re1121.2 (6)N2—C18—H18118.4
O1—C1—Re1179.3 (10)C17—C18—H18118.4
O2—C2—Re1177.2 (11)C20—C19—H19A109.5
O3—C3—Re1177.8 (10)C20—C19—H19B109.5
N1—C4—C5122.8 (9)H19A—C19—H19B109.5
N1—C4—H4118.6C20—C19—H19C109.5
C5—C4—H4118.6H19A—C19—H19C109.5
C6—C5—C4119.6 (9)H19B—C19—H19C109.5
C6—C5—H5120.2O6—C20—C21117.3 (11)
C4—C5—H5120.2O6—C20—C19117.4 (12)
C5—C6—C7117.4 (8)C21—C20—C19125.3 (11)
C5—C6—C11120.5 (9)C22—C21—C20122.3 (11)
C7—C6—C11122.0 (8)C22—C21—C16119.6 (9)
C8—C7—C6120.2 (8)C20—C21—C16118.0 (9)
C8—C7—H7119.9O7—C22—C21122.1 (11)
C6—C7—H7119.9O7—C22—C23115.2 (11)
N1—C8—C7121.5 (9)C21—C22—C23122.7 (11)
N1—C8—H8119.2C22—C23—H23A109.5
C7—C8—H8119.2C22—C23—H23B109.5
C10—C9—H9A109.5H23A—C23—H23B109.5
C10—C9—H9B109.5C22—C23—H23C109.5
H9A—C9—H9B109.5H23A—C23—H23C109.5
C10—C9—H9C109.5H23B—C23—H23C109.5
H9A—C9—H9C109.5Cl1S—C1S—Cl3S117.2 (10)
H9B—C9—H9C109.5Cl1S—C1S—Cl2S102.9 (8)
O4—C10—C11120.7 (8)Cl3S—C1S—Cl2S103.9 (9)
O4—C10—C9116.2 (8)Cl1S—C1S—H1S110.7
C11—C10—C9123.1 (8)Cl3S—C1S—H1S110.7
C12—C11—C10119.8 (8)Cl2S—C1S—H1S110.7
C3—Re1—N1—C4132.5 (7)C5—C6—C11—C1276.2 (12)
C1—Re1—N1—C4139.4 (7)C7—C6—C11—C1299.4 (11)
N2—Re1—N1—C447.2 (7)C5—C6—C11—C10102.1 (11)
Cl1—Re1—N1—C439.4 (7)C7—C6—C11—C1082.3 (12)
C3—Re1—N1—C843.5 (7)C10—C11—C12—O51.0 (15)
C1—Re1—N1—C844.6 (7)C6—C11—C12—O5177.3 (9)
N2—Re1—N1—C8136.8 (6)C10—C11—C12—C13176.5 (9)
Cl1—Re1—N1—C8136.6 (6)C6—C11—C12—C135.2 (15)
C2—Re1—N2—C14129.4 (7)C18—N2—C14—C152.1 (13)
C1—Re1—N2—C1438.7 (7)Re1—N2—C14—C15180.0 (7)
N1—Re1—N2—C1453.3 (6)N2—C14—C15—C161.8 (14)
Cl1—Re1—N2—C14138.4 (6)C14—C15—C16—C170.6 (14)
C2—Re1—N2—C1848.4 (7)C14—C15—C16—C21176.8 (9)
C1—Re1—N2—C18139.0 (7)C15—C16—C17—C180.1 (14)
N1—Re1—N2—C18129.0 (7)C21—C16—C17—C18176.3 (9)
Cl1—Re1—N2—C1843.8 (6)C14—N2—C18—C171.4 (13)
C8—N1—C4—C52.8 (13)Re1—N2—C18—C17179.3 (7)
Re1—N1—C4—C5178.9 (6)C16—C17—C18—N20.3 (14)
N1—C4—C5—C60.7 (14)O6—C20—C21—C220.0 (17)
C4—C5—C6—C72.0 (13)C19—C20—C21—C22179.6 (12)
C4—C5—C6—C11177.8 (8)O6—C20—C21—C16177.9 (10)
C5—C6—C7—C82.5 (13)C19—C20—C21—C161.8 (17)
C11—C6—C7—C8178.3 (7)C15—C16—C21—C22108.2 (12)
C4—N1—C8—C72.3 (12)C17—C16—C21—C2275.6 (13)
Re1—N1—C8—C7178.4 (6)C15—C16—C21—C2069.7 (14)
C6—C7—C8—N10.4 (13)C17—C16—C21—C20106.5 (11)
O4—C10—C11—C121.4 (15)C20—C21—C22—O70.3 (19)
C9—C10—C11—C12179.0 (10)C16—C21—C22—O7178.1 (10)
O4—C10—C11—C6176.9 (9)C20—C21—C22—C23177.3 (13)
C9—C10—C11—C62.7 (15)C16—C21—C22—C230.5 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O41.13 (11)1.46 (11)2.459 (9)144 (8)
O7—H7O···O61.06 (15)1.55 (14)2.486 (12)144 (13)
 

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