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The title compound, [Fe(C18H13NO2)(CO)3], is produced by the reaction of Fe2(CO)9 with an azlactone obtained from hippuric acid and cinnamaldehyde. Although, in principle, various coordination sites are possible in the ligand, the 1,3-butadiene subunit exclusively binds to the transition metal in an η4-fashion. The crystal structure is stabilized by inter­molecular inter­actions between the O atoms of the lactone and terminal carbon monoxide ligands and various CH groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019483/bt6683sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019483/bt66832sup2.hkl
Contains datablock 2

CCDC reference: 277213

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.097
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Datablock: 2


Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 13 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.50 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C20 .. 5.20 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - C21 .. 5.17 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - C19 .. 7.10 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - C20 .. 9.42 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - C21 .. 9.04 su PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O2 .. 2.70 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. O3 .. 2.67 Ang.
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 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 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: XP.

Tricarbonyl[η4-2-phenyl-4-(3-phenylallylidene)-4H-oxazol-5-onato]iron top
Crystal data top
[Fe(C18H13NO2)(CO)3]Z = 2
Mr = 415.17F(000) = 424
Triclinic, P1Dx = 1.526 Mg m3
a = 8.8352 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.0584 (7) ÅCell parameters from 3311 reflections
c = 11.4944 (8) Åθ = 1.9–27.5°
α = 71.20 (3)°µ = 0.87 mm1
β = 88.61 (4)°T = 173 K
γ = 69.86 (4)°Cuboid, orange
V = 903.5 (3) Å30.2 × 0.2 × 0.1 mm
Data collection top
Nonius KappaCCD
diffractometer
3311 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 27.5°, θmin = 1.9°
ω scansh = 1011
6679 measured reflectionsk = 1313
4041 independent reflectionsl = 1414
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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.097All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.1046P]
where P = (Fo2 + 2Fc2)/3
4041 reflections(Δ/σ)max < 0.001
305 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.46 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
Fe10.23819 (3)0.16475 (3)0.10021 (3)0.02457 (11)
C10.3281 (3)0.4673 (3)0.2164 (2)0.0346 (5)
H10.315 (3)0.408 (3)0.132 (3)0.050 (7)*
C20.4794 (3)0.5611 (3)0.2769 (3)0.0463 (6)
H20.563 (4)0.563 (3)0.237 (3)0.058 (8)*
C30.4940 (3)0.6505 (3)0.3991 (3)0.0477 (6)
H30.603 (3)0.724 (3)0.435 (3)0.063 (9)*
C40.3585 (3)0.6454 (3)0.4623 (2)0.0461 (6)
H40.370 (3)0.706 (3)0.543 (3)0.053 (8)*
C50.2069 (3)0.5522 (3)0.4028 (2)0.0365 (5)
H50.113 (3)0.548 (3)0.451 (2)0.046 (7)*
C60.1911 (2)0.4625 (2)0.28012 (18)0.0271 (4)
C70.0325 (2)0.3599 (2)0.21549 (18)0.0261 (4)
N10.00427 (19)0.25347 (18)0.11239 (15)0.0255 (4)
C80.2348 (2)0.2757 (2)0.19184 (19)0.0308 (5)
O10.10239 (16)0.38125 (16)0.27242 (13)0.0311 (3)
O20.37171 (18)0.26041 (19)0.21447 (15)0.0407 (4)
C90.1680 (2)0.1938 (2)0.08442 (18)0.0271 (4)
C100.2675 (2)0.0427 (2)0.01489 (19)0.0280 (4)
H100.362 (3)0.002 (3)0.040 (2)0.029 (6)*
C110.2222 (2)0.0360 (2)0.0960 (2)0.0284 (4)
H110.292 (3)0.124 (3)0.140 (2)0.032 (6)*
C120.0749 (2)0.0345 (2)0.13881 (19)0.0263 (4)
H120.008 (2)0.102 (2)0.0785 (19)0.018 (5)*
C130.0259 (2)0.0276 (2)0.26175 (19)0.0270 (4)
C140.1295 (3)0.1500 (2)0.3568 (2)0.0304 (4)
H140.229 (3)0.195 (3)0.347 (2)0.037 (6)*
C150.0733 (3)0.2072 (3)0.4683 (2)0.0362 (5)
H150.143 (3)0.293 (3)0.528 (2)0.044 (7)*
C160.0860 (3)0.1416 (3)0.4882 (2)0.0397 (5)
H160.123 (3)0.183 (3)0.575 (3)0.056 (8)*
C170.1902 (3)0.0202 (3)0.3963 (2)0.0404 (5)
H170.301 (3)0.026 (3)0.408 (2)0.050 (7)*
C180.1347 (3)0.0359 (3)0.2837 (2)0.0335 (5)
H180.201 (3)0.116 (3)0.221 (2)0.040 (7)*
C190.3430 (2)0.0771 (2)0.2529 (2)0.0312 (5)
O30.41067 (19)0.0206 (2)0.34959 (15)0.0456 (4)
C200.0667 (3)0.3146 (2)0.12137 (19)0.0303 (5)
O40.0466 (2)0.40482 (19)0.13279 (17)0.0458 (4)
C210.3815 (3)0.2573 (3)0.0513 (2)0.0334 (5)
O50.4721 (2)0.3171 (2)0.02361 (17)0.0497 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02215 (16)0.02580 (17)0.02732 (17)0.00957 (12)0.00341 (11)0.00985 (12)
C10.0320 (11)0.0354 (12)0.0320 (12)0.0128 (9)0.0047 (9)0.0049 (10)
C20.0278 (12)0.0537 (16)0.0509 (16)0.0136 (11)0.0068 (11)0.0102 (13)
C30.0338 (12)0.0475 (15)0.0482 (15)0.0089 (11)0.0069 (11)0.0037 (12)
C40.0448 (14)0.0418 (14)0.0359 (14)0.0073 (11)0.0022 (11)0.0011 (11)
C50.0396 (12)0.0330 (12)0.0314 (12)0.0108 (10)0.0083 (10)0.0062 (9)
C60.0305 (10)0.0231 (10)0.0285 (11)0.0110 (8)0.0024 (8)0.0081 (8)
C70.0274 (10)0.0288 (10)0.0277 (10)0.0139 (8)0.0067 (8)0.0127 (9)
N10.0261 (8)0.0261 (8)0.0263 (9)0.0105 (7)0.0019 (7)0.0099 (7)
C80.0311 (11)0.0341 (11)0.0293 (11)0.0118 (9)0.0064 (9)0.0132 (9)
O10.0292 (7)0.0334 (8)0.0294 (8)0.0131 (6)0.0072 (6)0.0069 (6)
O20.0296 (8)0.0547 (10)0.0379 (9)0.0176 (7)0.0112 (7)0.0134 (8)
C90.0260 (10)0.0316 (11)0.0269 (10)0.0122 (8)0.0049 (8)0.0123 (9)
C100.0255 (10)0.0300 (10)0.0311 (11)0.0086 (8)0.0059 (8)0.0152 (9)
C110.0302 (10)0.0220 (10)0.0339 (12)0.0089 (9)0.0010 (9)0.0108 (9)
C120.0253 (10)0.0259 (10)0.0304 (11)0.0120 (8)0.0005 (8)0.0094 (9)
C130.0284 (10)0.0286 (10)0.0309 (11)0.0159 (8)0.0035 (8)0.0129 (9)
C140.0294 (11)0.0296 (11)0.0337 (12)0.0133 (9)0.0039 (9)0.0095 (9)
C150.0428 (13)0.0358 (12)0.0316 (12)0.0201 (10)0.0015 (10)0.0064 (10)
C160.0475 (13)0.0454 (14)0.0372 (13)0.0291 (11)0.0141 (11)0.0152 (11)
C170.0334 (12)0.0508 (14)0.0456 (14)0.0218 (11)0.0118 (10)0.0203 (12)
C180.0283 (11)0.0368 (12)0.0364 (12)0.0138 (9)0.0023 (9)0.0112 (10)
C190.0248 (10)0.0371 (12)0.0349 (12)0.0140 (9)0.0056 (9)0.0133 (10)
O30.0373 (9)0.0608 (11)0.0349 (9)0.0193 (8)0.0041 (7)0.0088 (8)
C200.0336 (11)0.0308 (11)0.0314 (11)0.0158 (9)0.0037 (9)0.0120 (9)
O40.0400 (9)0.0380 (9)0.0608 (11)0.0064 (8)0.0106 (8)0.0265 (8)
C210.0331 (11)0.0362 (12)0.0333 (12)0.0128 (10)0.0078 (9)0.0146 (10)
O50.0501 (10)0.0653 (12)0.0552 (11)0.0406 (9)0.0213 (9)0.0275 (9)
Geometric parameters (Å, º) top
Fe1—C211.797 (2)C8—O11.385 (3)
Fe1—C191.798 (2)C8—C91.482 (3)
Fe1—C201.809 (2)C9—C101.433 (3)
Fe1—C102.034 (2)C10—C111.398 (3)
Fe1—C112.088 (2)C10—H100.88 (2)
Fe1—C92.125 (2)C11—C121.413 (3)
Fe1—C122.211 (2)C11—H110.88 (2)
C1—C21.384 (3)C12—C131.470 (3)
C1—C61.394 (3)C12—H120.92 (2)
C1—H10.95 (3)C13—C181.395 (3)
C2—C31.383 (4)C13—C141.397 (3)
C2—H20.86 (3)C14—C151.382 (3)
C3—C41.379 (4)C14—H140.87 (2)
C3—H30.99 (3)C15—C161.383 (3)
C4—C51.381 (3)C15—H150.93 (3)
C4—H40.92 (3)C16—C171.377 (4)
C5—C61.388 (3)C16—H161.04 (3)
C5—H50.98 (3)C17—C181.386 (3)
C6—C71.463 (3)C17—H170.96 (3)
C7—N11.275 (3)C18—H180.91 (3)
C7—O11.394 (2)C19—O31.144 (3)
N1—C91.432 (2)C20—O41.135 (3)
C8—O21.199 (2)C21—O51.140 (3)
C21—Fe1—C1989.93 (10)C8—O1—C7105.23 (15)
C21—Fe1—C20101.59 (9)N1—C9—C10127.69 (18)
C19—Fe1—C20101.34 (10)N1—C9—C8106.43 (17)
C21—Fe1—C10101.71 (9)C10—C9—C8117.39 (18)
C19—Fe1—C10119.60 (9)N1—C9—Fe1112.47 (13)
C20—Fe1—C10132.36 (9)C10—C9—Fe166.47 (12)
C21—Fe1—C11134.00 (9)C8—C9—Fe1122.40 (14)
C19—Fe1—C1192.63 (10)C11—C10—C9120.95 (19)
C20—Fe1—C11122.73 (9)C11—C10—Fe172.28 (12)
C10—Fe1—C1139.62 (8)C9—C10—Fe173.29 (12)
C21—Fe1—C992.07 (9)C11—C10—H10120.1 (14)
C19—Fe1—C9159.59 (9)C9—C10—H10118.8 (14)
C20—Fe1—C998.14 (9)Fe1—C10—H10122.6 (15)
C10—Fe1—C940.23 (8)C10—C11—C12119.24 (19)
C11—Fe1—C971.56 (9)C10—C11—Fe168.10 (12)
C21—Fe1—C12171.24 (9)C12—C11—Fe175.61 (12)
C19—Fe1—C1294.32 (9)C10—C11—H11117.8 (15)
C20—Fe1—C1285.09 (8)C12—C11—H11122.6 (15)
C10—Fe1—C1269.54 (8)Fe1—C11—H11122.1 (15)
C11—Fe1—C1238.25 (8)C11—C12—C13124.06 (19)
C9—Fe1—C1281.29 (8)C11—C12—Fe166.14 (11)
C2—C1—C6119.4 (2)C13—C12—Fe1124.37 (14)
C2—C1—H1121.6 (16)C11—C12—H12115.8 (12)
C6—C1—H1119.0 (16)C13—C12—H12116.3 (12)
C3—C2—C1120.2 (2)Fe1—C12—H1297.3 (12)
C3—C2—H2121.2 (19)C18—C13—C14117.9 (2)
C1—C2—H2119 (2)C18—C13—C12118.21 (19)
C4—C3—C2120.4 (2)C14—C13—C12123.81 (18)
C4—C3—H3122.3 (17)C15—C14—C13120.7 (2)
C2—C3—H3117.0 (17)C15—C14—H14117.8 (16)
C3—C4—C5119.9 (2)C13—C14—H14121.4 (16)
C3—C4—H4119.7 (17)C14—C15—C16120.3 (2)
C5—C4—H4120.4 (17)C14—C15—H15118.7 (16)
C4—C5—C6120.0 (2)C16—C15—H15121.0 (16)
C4—C5—H5118.2 (15)C17—C16—C15120.1 (2)
C6—C5—H5121.7 (15)C17—C16—H16121.3 (15)
C5—C6—C1120.1 (2)C15—C16—H16118.6 (15)
C5—C6—C7121.30 (19)C16—C17—C18119.8 (2)
C1—C6—C7118.61 (19)C16—C17—H17121.6 (16)
N1—C7—O1116.43 (18)C18—C17—H17118.6 (16)
N1—C7—C6127.05 (18)C17—C18—C13121.2 (2)
O1—C7—C6116.52 (17)C17—C18—H18122.0 (15)
C7—N1—C9105.78 (16)C13—C18—H18116.8 (15)
O2—C8—O1122.67 (19)O3—C19—Fe1179.4 (2)
O2—C8—C9131.3 (2)O4—C20—Fe1175.97 (19)
O1—C8—C9105.98 (16)O5—C21—Fe1177.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.92 (3)2.70 (3)3.520 (3)150 (2)
C17—H17···O3ii0.96 (3)2.67 (3)3.442 (3)138 (2)
Symmetry codes: (i) x, y+1, z1; (ii) x1, y, z.
 

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