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
CCDC reference: 277213
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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)-4
H-oxazol-5-onato]iron
top
Crystal data top
[Fe(C18H13NO2)(CO)3] | Z = 2 |
Mr = 415.17 | F(000) = 424 |
Triclinic, P1 | Dx = 1.526 Mg m−3 |
a = 8.8352 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.0584 (7) Å | Cell parameters from 3311 reflections |
c = 11.4944 (8) Å | θ = 1.9–27.5° |
α = 71.20 (3)° | µ = 0.87 mm−1 |
β = 88.61 (4)° | T = 173 K |
γ = 69.86 (4)° | Cuboid, orange |
V = 903.5 (3) Å3 | 0.2 × 0.2 × 0.1 mm |
Data collection top
Nonius KappaCCD diffractometer | 3311 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
ω scans | h = −10→11 |
6679 measured reflections | k = −13→13 |
4041 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.097 | All 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 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−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 | x | y | z | Uiso*/Ueq | |
Fe1 | 0.23819 (3) | 0.16475 (3) | 0.10021 (3) | 0.02457 (11) | |
C1 | −0.3281 (3) | 0.4673 (3) | −0.2164 (2) | 0.0346 (5) | |
H1 | −0.315 (3) | 0.408 (3) | −0.132 (3) | 0.050 (7)* | |
C2 | −0.4794 (3) | 0.5611 (3) | −0.2769 (3) | 0.0463 (6) | |
H2 | −0.563 (4) | 0.563 (3) | −0.237 (3) | 0.058 (8)* | |
C3 | −0.4940 (3) | 0.6505 (3) | −0.3991 (3) | 0.0477 (6) | |
H3 | −0.603 (3) | 0.724 (3) | −0.435 (3) | 0.063 (9)* | |
C4 | −0.3585 (3) | 0.6454 (3) | −0.4623 (2) | 0.0461 (6) | |
H4 | −0.370 (3) | 0.706 (3) | −0.543 (3) | 0.053 (8)* | |
C5 | −0.2069 (3) | 0.5522 (3) | −0.4028 (2) | 0.0365 (5) | |
H5 | −0.113 (3) | 0.548 (3) | −0.451 (2) | 0.046 (7)* | |
C6 | −0.1911 (2) | 0.4625 (2) | −0.28012 (18) | 0.0271 (4) | |
C7 | −0.0325 (2) | 0.3599 (2) | −0.21549 (18) | 0.0261 (4) | |
N1 | −0.00427 (19) | 0.25347 (18) | −0.11239 (15) | 0.0255 (4) | |
C8 | 0.2348 (2) | 0.2757 (2) | −0.19184 (19) | 0.0308 (5) | |
O1 | 0.10239 (16) | 0.38125 (16) | −0.27242 (13) | 0.0311 (3) | |
O2 | 0.37171 (18) | 0.26041 (19) | −0.21447 (15) | 0.0407 (4) | |
C9 | 0.1680 (2) | 0.1938 (2) | −0.08442 (18) | 0.0271 (4) | |
C10 | 0.2675 (2) | 0.0427 (2) | −0.01489 (19) | 0.0280 (4) | |
H10 | 0.362 (3) | 0.002 (3) | −0.040 (2) | 0.029 (6)* | |
C11 | 0.2222 (2) | −0.0360 (2) | 0.0960 (2) | 0.0284 (4) | |
H11 | 0.292 (3) | −0.124 (3) | 0.140 (2) | 0.032 (6)* | |
C12 | 0.0749 (2) | 0.0345 (2) | 0.13881 (19) | 0.0263 (4) | |
H12 | −0.008 (2) | 0.102 (2) | 0.0785 (19) | 0.018 (5)* | |
C13 | 0.0259 (2) | −0.0276 (2) | 0.26175 (19) | 0.0270 (4) | |
C14 | 0.1295 (3) | −0.1500 (2) | 0.3568 (2) | 0.0304 (4) | |
H14 | 0.229 (3) | −0.195 (3) | 0.347 (2) | 0.037 (6)* | |
C15 | 0.0733 (3) | −0.2072 (3) | 0.4683 (2) | 0.0362 (5) | |
H15 | 0.143 (3) | −0.293 (3) | 0.528 (2) | 0.044 (7)* | |
C16 | −0.0860 (3) | −0.1416 (3) | 0.4882 (2) | 0.0397 (5) | |
H16 | −0.123 (3) | −0.183 (3) | 0.575 (3) | 0.056 (8)* | |
C17 | −0.1902 (3) | −0.0202 (3) | 0.3963 (2) | 0.0404 (5) | |
H17 | −0.301 (3) | 0.026 (3) | 0.408 (2) | 0.050 (7)* | |
C18 | −0.1347 (3) | 0.0359 (3) | 0.2837 (2) | 0.0335 (5) | |
H18 | −0.201 (3) | 0.116 (3) | 0.221 (2) | 0.040 (7)* | |
C19 | 0.3430 (2) | 0.0771 (2) | 0.2529 (2) | 0.0312 (5) | |
O3 | 0.41067 (19) | 0.0206 (2) | 0.34959 (15) | 0.0456 (4) | |
C20 | 0.0667 (3) | 0.3146 (2) | 0.12137 (19) | 0.0303 (5) | |
O4 | −0.0466 (2) | 0.40482 (19) | 0.13279 (17) | 0.0458 (4) | |
C21 | 0.3815 (3) | 0.2573 (3) | 0.0513 (2) | 0.0334 (5) | |
O5 | 0.4721 (2) | 0.3171 (2) | 0.02361 (17) | 0.0497 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.02215 (16) | 0.02580 (17) | 0.02732 (17) | −0.00957 (12) | 0.00341 (11) | −0.00985 (12) |
C1 | 0.0320 (11) | 0.0354 (12) | 0.0320 (12) | −0.0128 (9) | 0.0047 (9) | −0.0049 (10) |
C2 | 0.0278 (12) | 0.0537 (16) | 0.0509 (16) | −0.0136 (11) | 0.0068 (11) | −0.0102 (13) |
C3 | 0.0338 (12) | 0.0475 (15) | 0.0482 (15) | −0.0089 (11) | −0.0069 (11) | −0.0037 (12) |
C4 | 0.0448 (14) | 0.0418 (14) | 0.0359 (14) | −0.0073 (11) | −0.0022 (11) | −0.0011 (11) |
C5 | 0.0396 (12) | 0.0330 (12) | 0.0314 (12) | −0.0108 (10) | 0.0083 (10) | −0.0062 (9) |
C6 | 0.0305 (10) | 0.0231 (10) | 0.0285 (11) | −0.0110 (8) | 0.0024 (8) | −0.0081 (8) |
C7 | 0.0274 (10) | 0.0288 (10) | 0.0277 (10) | −0.0139 (8) | 0.0067 (8) | −0.0127 (9) |
N1 | 0.0261 (8) | 0.0261 (8) | 0.0263 (9) | −0.0105 (7) | 0.0019 (7) | −0.0099 (7) |
C8 | 0.0311 (11) | 0.0341 (11) | 0.0293 (11) | −0.0118 (9) | 0.0064 (9) | −0.0132 (9) |
O1 | 0.0292 (7) | 0.0334 (8) | 0.0294 (8) | −0.0131 (6) | 0.0072 (6) | −0.0069 (6) |
O2 | 0.0296 (8) | 0.0547 (10) | 0.0379 (9) | −0.0176 (7) | 0.0112 (7) | −0.0134 (8) |
C9 | 0.0260 (10) | 0.0316 (11) | 0.0269 (10) | −0.0122 (8) | 0.0049 (8) | −0.0123 (9) |
C10 | 0.0255 (10) | 0.0300 (10) | 0.0311 (11) | −0.0086 (8) | 0.0059 (8) | −0.0152 (9) |
C11 | 0.0302 (10) | 0.0220 (10) | 0.0339 (12) | −0.0089 (9) | 0.0010 (9) | −0.0108 (9) |
C12 | 0.0253 (10) | 0.0259 (10) | 0.0304 (11) | −0.0120 (8) | −0.0005 (8) | −0.0094 (9) |
C13 | 0.0284 (10) | 0.0286 (10) | 0.0309 (11) | −0.0159 (8) | 0.0035 (8) | −0.0129 (9) |
C14 | 0.0294 (11) | 0.0296 (11) | 0.0337 (12) | −0.0133 (9) | 0.0039 (9) | −0.0095 (9) |
C15 | 0.0428 (13) | 0.0358 (12) | 0.0316 (12) | −0.0201 (10) | 0.0015 (10) | −0.0064 (10) |
C16 | 0.0475 (13) | 0.0454 (14) | 0.0372 (13) | −0.0291 (11) | 0.0141 (11) | −0.0152 (11) |
C17 | 0.0334 (12) | 0.0508 (14) | 0.0456 (14) | −0.0218 (11) | 0.0118 (10) | −0.0203 (12) |
C18 | 0.0283 (11) | 0.0368 (12) | 0.0364 (12) | −0.0138 (9) | 0.0023 (9) | −0.0112 (10) |
C19 | 0.0248 (10) | 0.0371 (12) | 0.0349 (12) | −0.0140 (9) | 0.0056 (9) | −0.0133 (10) |
O3 | 0.0373 (9) | 0.0608 (11) | 0.0349 (9) | −0.0193 (8) | −0.0041 (7) | −0.0088 (8) |
C20 | 0.0336 (11) | 0.0308 (11) | 0.0314 (11) | −0.0158 (9) | 0.0037 (9) | −0.0120 (9) |
O4 | 0.0400 (9) | 0.0380 (9) | 0.0608 (11) | −0.0064 (8) | 0.0106 (8) | −0.0265 (8) |
C21 | 0.0331 (11) | 0.0362 (12) | 0.0333 (12) | −0.0128 (10) | 0.0078 (9) | −0.0146 (10) |
O5 | 0.0501 (10) | 0.0653 (12) | 0.0552 (11) | −0.0406 (9) | 0.0213 (9) | −0.0275 (9) |
Geometric parameters (Å, º) top
Fe1—C21 | 1.797 (2) | C8—O1 | 1.385 (3) |
Fe1—C19 | 1.798 (2) | C8—C9 | 1.482 (3) |
Fe1—C20 | 1.809 (2) | C9—C10 | 1.433 (3) |
Fe1—C10 | 2.034 (2) | C10—C11 | 1.398 (3) |
Fe1—C11 | 2.088 (2) | C10—H10 | 0.88 (2) |
Fe1—C9 | 2.125 (2) | C11—C12 | 1.413 (3) |
Fe1—C12 | 2.211 (2) | C11—H11 | 0.88 (2) |
C1—C2 | 1.384 (3) | C12—C13 | 1.470 (3) |
C1—C6 | 1.394 (3) | C12—H12 | 0.92 (2) |
C1—H1 | 0.95 (3) | C13—C18 | 1.395 (3) |
C2—C3 | 1.383 (4) | C13—C14 | 1.397 (3) |
C2—H2 | 0.86 (3) | C14—C15 | 1.382 (3) |
C3—C4 | 1.379 (4) | C14—H14 | 0.87 (2) |
C3—H3 | 0.99 (3) | C15—C16 | 1.383 (3) |
C4—C5 | 1.381 (3) | C15—H15 | 0.93 (3) |
C4—H4 | 0.92 (3) | C16—C17 | 1.377 (4) |
C5—C6 | 1.388 (3) | C16—H16 | 1.04 (3) |
C5—H5 | 0.98 (3) | C17—C18 | 1.386 (3) |
C6—C7 | 1.463 (3) | C17—H17 | 0.96 (3) |
C7—N1 | 1.275 (3) | C18—H18 | 0.91 (3) |
C7—O1 | 1.394 (2) | C19—O3 | 1.144 (3) |
N1—C9 | 1.432 (2) | C20—O4 | 1.135 (3) |
C8—O2 | 1.199 (2) | C21—O5 | 1.140 (3) |
| | | |
C21—Fe1—C19 | 89.93 (10) | C8—O1—C7 | 105.23 (15) |
C21—Fe1—C20 | 101.59 (9) | N1—C9—C10 | 127.69 (18) |
C19—Fe1—C20 | 101.34 (10) | N1—C9—C8 | 106.43 (17) |
C21—Fe1—C10 | 101.71 (9) | C10—C9—C8 | 117.39 (18) |
C19—Fe1—C10 | 119.60 (9) | N1—C9—Fe1 | 112.47 (13) |
C20—Fe1—C10 | 132.36 (9) | C10—C9—Fe1 | 66.47 (12) |
C21—Fe1—C11 | 134.00 (9) | C8—C9—Fe1 | 122.40 (14) |
C19—Fe1—C11 | 92.63 (10) | C11—C10—C9 | 120.95 (19) |
C20—Fe1—C11 | 122.73 (9) | C11—C10—Fe1 | 72.28 (12) |
C10—Fe1—C11 | 39.62 (8) | C9—C10—Fe1 | 73.29 (12) |
C21—Fe1—C9 | 92.07 (9) | C11—C10—H10 | 120.1 (14) |
C19—Fe1—C9 | 159.59 (9) | C9—C10—H10 | 118.8 (14) |
C20—Fe1—C9 | 98.14 (9) | Fe1—C10—H10 | 122.6 (15) |
C10—Fe1—C9 | 40.23 (8) | C10—C11—C12 | 119.24 (19) |
C11—Fe1—C9 | 71.56 (9) | C10—C11—Fe1 | 68.10 (12) |
C21—Fe1—C12 | 171.24 (9) | C12—C11—Fe1 | 75.61 (12) |
C19—Fe1—C12 | 94.32 (9) | C10—C11—H11 | 117.8 (15) |
C20—Fe1—C12 | 85.09 (8) | C12—C11—H11 | 122.6 (15) |
C10—Fe1—C12 | 69.54 (8) | Fe1—C11—H11 | 122.1 (15) |
C11—Fe1—C12 | 38.25 (8) | C11—C12—C13 | 124.06 (19) |
C9—Fe1—C12 | 81.29 (8) | C11—C12—Fe1 | 66.14 (11) |
C2—C1—C6 | 119.4 (2) | C13—C12—Fe1 | 124.37 (14) |
C2—C1—H1 | 121.6 (16) | C11—C12—H12 | 115.8 (12) |
C6—C1—H1 | 119.0 (16) | C13—C12—H12 | 116.3 (12) |
C3—C2—C1 | 120.2 (2) | Fe1—C12—H12 | 97.3 (12) |
C3—C2—H2 | 121.2 (19) | C18—C13—C14 | 117.9 (2) |
C1—C2—H2 | 119 (2) | C18—C13—C12 | 118.21 (19) |
C4—C3—C2 | 120.4 (2) | C14—C13—C12 | 123.81 (18) |
C4—C3—H3 | 122.3 (17) | C15—C14—C13 | 120.7 (2) |
C2—C3—H3 | 117.0 (17) | C15—C14—H14 | 117.8 (16) |
C3—C4—C5 | 119.9 (2) | C13—C14—H14 | 121.4 (16) |
C3—C4—H4 | 119.7 (17) | C14—C15—C16 | 120.3 (2) |
C5—C4—H4 | 120.4 (17) | C14—C15—H15 | 118.7 (16) |
C4—C5—C6 | 120.0 (2) | C16—C15—H15 | 121.0 (16) |
C4—C5—H5 | 118.2 (15) | C17—C16—C15 | 120.1 (2) |
C6—C5—H5 | 121.7 (15) | C17—C16—H16 | 121.3 (15) |
C5—C6—C1 | 120.1 (2) | C15—C16—H16 | 118.6 (15) |
C5—C6—C7 | 121.30 (19) | C16—C17—C18 | 119.8 (2) |
C1—C6—C7 | 118.61 (19) | C16—C17—H17 | 121.6 (16) |
N1—C7—O1 | 116.43 (18) | C18—C17—H17 | 118.6 (16) |
N1—C7—C6 | 127.05 (18) | C17—C18—C13 | 121.2 (2) |
O1—C7—C6 | 116.52 (17) | C17—C18—H18 | 122.0 (15) |
C7—N1—C9 | 105.78 (16) | C13—C18—H18 | 116.8 (15) |
O2—C8—O1 | 122.67 (19) | O3—C19—Fe1 | 179.4 (2) |
O2—C8—C9 | 131.3 (2) | O4—C20—Fe1 | 175.97 (19) |
O1—C8—C9 | 105.98 (16) | O5—C21—Fe1 | 177.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.92 (3) | 2.70 (3) | 3.520 (3) | 150 (2) |
C17—H17···O3ii | 0.96 (3) | 2.67 (3) | 3.442 (3) | 138 (2) |
Symmetry codes: (i) −x, −y+1, −z−1; (ii) x−1, y, z. |