[N-(Benzyl­idene)­aniline-N]­pentacarbonyl­chromium(0)

In the title compound, [Cr(C₁₃H₁₁N)(CO)₅], the imino ligand displays weak [pi]-acceptor capabilities and, in contrast to Fischer-type carbene complexes, is not positioned on the bisecting line of the angle between two CO ligands.

Computing details

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

N-benzylideneaniline(pentacarbonyl)chromium(0)

Crystal data

[Cr(C13H11N)(CO)5]	F(000) = 760
Mr = 373.28	Dx = 1.494 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.0959 (12) Å	Cell parameters from 20447 reflections
b = 15.3703 (13) Å	θ = 2.5–28.3°
c = 8.7107 (3) Å	µ = 0.72 mm^−1
β = 108.860 (4)°	T = 123 K
V = 1659.2 (2) Å^3	Plates, yellow
Z = 4	0.25 × 0.10 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer	2915 independent reflections
Radiation source: fine-focus sealed tube	2344 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
rotation in φ and ω (1°) scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan MULABS in PLATON98 (Spek, 1990; cf. Blessing, 1995)	h = −15→15
Tmin = 0.822, Tmax = 0.922	k = −18→18
17681 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 0.3439P] where P = (Fo^2 + 2Fc^2)/3
2915 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.56 e Å^−3

Special details

Experimental. dx = 39.803 (6) mm; 2 x 60 sec., 1 °., 543 frames, 5 sets; mos.= 1.963 (3) °.

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 (Ų)

	x	y	z	Uiso*/Ueq
Cr1	0.26075 (3)	0.51730 (2)	0.20486 (4)	0.02347 (14)
C1A	0.31017 (19)	0.56995 (16)	0.0520 (3)	0.0275 (6)
O1A	0.33872 (14)	0.60215 (12)	−0.04711 (19)	0.0363 (4)
C1B	0.31374 (19)	0.61610 (17)	0.3441 (3)	0.0272 (5)
O1B	0.34797 (14)	0.67693 (12)	0.4169 (2)	0.0384 (4)
C1C	0.21360 (19)	0.42178 (16)	0.0615 (3)	0.0274 (5)
O1C	0.18805 (14)	0.36585 (12)	−0.0295 (2)	0.0396 (5)
C1D	0.3982 (2)	0.45997 (17)	0.2901 (3)	0.0293 (6)
O1D	0.47978 (15)	0.42661 (12)	0.3286 (2)	0.0422 (5)
C1E	0.1265 (2)	0.57310 (15)	0.1034 (3)	0.0264 (5)
O1E	0.04637 (14)	0.60532 (11)	0.03171 (19)	0.0334 (4)
N1	0.19776 (15)	0.45218 (12)	0.3757 (2)	0.0230 (4)
C2	0.09665 (19)	0.44541 (15)	0.3571 (3)	0.0245 (5)
H2	0.0525	0.4809	0.2722	0.029*
C11	0.27539 (18)	0.40587 (15)	0.5063 (2)	0.0231 (5)
C12	0.3059 (2)	0.32183 (15)	0.4811 (3)	0.0286 (6)
H12	0.2738	0.2939	0.3796	0.034*
C13	0.3831 (2)	0.27921 (16)	0.6051 (3)	0.0318 (6)
H13	0.4039	0.2216	0.5886	0.038*
C14	0.4304 (2)	0.31980 (17)	0.7527 (3)	0.0318 (6)
H14	0.4835	0.2903	0.8374	0.038*
C15	0.39993 (19)	0.40386 (17)	0.7767 (3)	0.0306 (6)
H15	0.4319	0.4317	0.8783	0.037*
C16	0.32329 (19)	0.44733 (16)	0.6532 (3)	0.0270 (5)
H16	0.3036	0.5053	0.6691	0.032*
C21	0.03489 (18)	0.39427 (14)	0.4396 (2)	0.0228 (5)
C22	−0.07604 (19)	0.39020 (15)	0.3589 (3)	0.0259 (5)
H22	−0.1059	0.4220	0.2611	0.031*
C23	−0.1436 (2)	0.34075 (16)	0.4183 (3)	0.0285 (6)
H23	−0.2187	0.3381	0.3608	0.034*
C24	−0.1005 (2)	0.29531 (15)	0.5618 (3)	0.0278 (5)
H24	−0.1460	0.2606	0.6025	0.033*
C25	0.0081 (2)	0.30037 (16)	0.6457 (3)	0.0291 (6)
H25	0.0366	0.2703	0.7458	0.035*
C26	0.0765 (2)	0.34849 (15)	0.5866 (3)	0.0278 (5)
H26	0.1515	0.3506	0.6452	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr1	0.0253 (2)	0.0215 (2)	0.0231 (2)	−0.00141 (16)	0.00705 (16)	0.00132 (15)
C1A	0.0277 (14)	0.0255 (14)	0.0262 (12)	0.0006 (10)	0.0043 (11)	−0.0026 (10)
O1A	0.0393 (11)	0.0416 (11)	0.0295 (9)	−0.0047 (9)	0.0130 (8)	0.0055 (8)
C1B	0.0257 (13)	0.0295 (15)	0.0277 (12)	0.0019 (11)	0.0107 (10)	0.0045 (11)
O1B	0.0375 (11)	0.0308 (11)	0.0459 (10)	−0.0065 (9)	0.0119 (8)	−0.0113 (9)
C1C	0.0229 (13)	0.0318 (15)	0.0280 (12)	0.0033 (11)	0.0087 (10)	0.0048 (11)
O1C	0.0385 (11)	0.0363 (11)	0.0395 (10)	0.0015 (8)	0.0066 (8)	−0.0123 (9)
C1D	0.0320 (15)	0.0277 (14)	0.0283 (12)	−0.0074 (12)	0.0099 (11)	0.0032 (10)
O1D	0.0279 (11)	0.0381 (12)	0.0580 (12)	0.0029 (9)	0.0102 (9)	0.0127 (9)
C1E	0.0330 (15)	0.0229 (13)	0.0247 (11)	−0.0047 (11)	0.0114 (11)	0.0008 (10)
O1E	0.0324 (10)	0.0302 (10)	0.0357 (9)	0.0038 (8)	0.0085 (8)	0.0061 (8)
N1	0.0265 (12)	0.0203 (10)	0.0214 (9)	−0.0005 (8)	0.0066 (8)	−0.0003 (8)
C2	0.0289 (14)	0.0208 (13)	0.0224 (11)	0.0005 (10)	0.0065 (10)	0.0003 (9)
C11	0.0248 (13)	0.0207 (13)	0.0251 (11)	−0.0029 (10)	0.0097 (10)	0.0029 (9)
C12	0.0370 (15)	0.0239 (14)	0.0257 (11)	−0.0031 (11)	0.0111 (11)	−0.0002 (10)
C13	0.0365 (15)	0.0229 (14)	0.0396 (14)	0.0045 (11)	0.0172 (12)	0.0058 (11)
C14	0.0280 (14)	0.0360 (16)	0.0309 (13)	0.0014 (11)	0.0087 (11)	0.0128 (11)
C15	0.0281 (14)	0.0343 (16)	0.0267 (12)	−0.0058 (11)	0.0053 (10)	−0.0006 (11)
C16	0.0284 (14)	0.0239 (13)	0.0289 (12)	−0.0031 (10)	0.0094 (10)	0.0008 (10)
C21	0.0297 (13)	0.0166 (12)	0.0226 (11)	0.0000 (10)	0.0090 (10)	−0.0026 (9)
C22	0.0317 (14)	0.0224 (13)	0.0237 (11)	0.0024 (10)	0.0089 (10)	0.0002 (10)
C23	0.0268 (14)	0.0284 (14)	0.0300 (12)	0.0000 (11)	0.0087 (10)	−0.0029 (10)
C24	0.0338 (15)	0.0202 (13)	0.0342 (12)	−0.0027 (10)	0.0174 (11)	−0.0013 (10)
C25	0.0340 (15)	0.0254 (14)	0.0281 (12)	0.0006 (11)	0.0103 (11)	0.0057 (10)
C26	0.0298 (14)	0.0264 (14)	0.0261 (11)	−0.0020 (10)	0.0075 (10)	−0.0020 (10)

Geometric parameters (Å, º)

Cr1—C1A	1.845 (2)	C2—C21	1.471 (3)
Cr1—C1C	1.897 (3)	C11—C16	1.385 (3)
Cr1—C1E	1.899 (3)	C11—C12	1.390 (3)
Cr1—C1D	1.925 (3)	C12—C13	1.383 (3)
Cr1—C1B	1.927 (3)	C13—C14	1.383 (3)
Cr1—N1	2.1659 (18)	C14—C15	1.388 (4)
C1A—O1A	1.157 (3)	C15—C16	1.383 (3)
C1B—O1B	1.137 (3)	C21—C22	1.396 (3)
C1C—O1C	1.144 (3)	C21—C26	1.407 (3)
C1D—O1D	1.133 (3)	C22—C23	1.387 (3)
C1E—O1E	1.145 (3)	C23—C24	1.384 (3)
N1—C2	1.285 (3)	C24—C25	1.375 (3)
N1—C11	1.444 (3)	C25—C26	1.383 (3)
C1A—Cr1—C1C	88.86 (10)	C2—N1—C11	119.58 (19)
C1A—Cr1—C1E	87.37 (10)	C2—N1—Cr1	123.82 (15)
C1C—Cr1—C1E	89.30 (10)	C11—N1—Cr1	116.19 (14)
C1A—Cr1—C1D	88.65 (10)	N1—C2—C21	133.5 (2)
C1C—Cr1—C1D	87.96 (10)	C16—C11—C12	120.4 (2)
C1E—Cr1—C1D	175.21 (10)	C16—C11—N1	119.6 (2)
C1A—Cr1—C1B	88.26 (10)	C12—C11—N1	119.92 (19)
C1C—Cr1—C1B	176.94 (10)	C13—C12—C11	119.5 (2)
C1E—Cr1—C1B	91.60 (10)	C14—C13—C12	120.5 (2)
C1D—Cr1—C1B	90.94 (10)	C13—C14—C15	119.7 (2)
C1A—Cr1—N1	177.46 (9)	C16—C15—C14	120.3 (2)
C1C—Cr1—N1	88.82 (8)	C15—C16—C11	119.6 (2)
C1E—Cr1—N1	91.57 (8)	C22—C21—C26	118.0 (2)
C1D—Cr1—N1	92.30 (8)	C22—C21—C2	115.15 (19)
C1B—Cr1—N1	94.08 (8)	C26—C21—C2	126.8 (2)
O1A—C1A—Cr1	178.1 (2)	C23—C22—C21	121.5 (2)
O1B—C1B—Cr1	174.5 (2)	C24—C23—C22	119.4 (2)
O1C—C1C—Cr1	176.6 (2)	C25—C24—C23	120.1 (2)
O1D—C1D—Cr1	174.7 (2)	C24—C25—C26	121.0 (2)
O1E—C1E—Cr1	175.08 (19)	C25—C26—C21	120.0 (2)
C1C—Cr1—C1A—O1A	39 (7)	C1A—Cr1—N1—C11	123 (2)
C1E—Cr1—C1A—O1A	−50 (7)	C1C—Cr1—N1—C11	99.13 (16)
C1D—Cr1—C1A—O1A	127 (7)	C1E—Cr1—N1—C11	−171.60 (16)
C1B—Cr1—C1A—O1A	−142 (7)	C1D—Cr1—N1—C11	11.22 (16)
N1—Cr1—C1A—O1A	15 (8)	C1B—Cr1—N1—C11	−79.89 (16)
C1A—Cr1—C1B—O1B	−2 (2)	C11—N1—C2—C21	−3.5 (4)
C1C—Cr1—C1B—O1B	18 (4)	Cr1—N1—C2—C21	168.79 (18)
C1E—Cr1—C1B—O1B	−89 (2)	C2—N1—C11—C16	−93.8 (3)
C1D—Cr1—C1B—O1B	86 (2)	Cr1—N1—C11—C16	93.3 (2)
N1—Cr1—C1B—O1B	179 (100)	C2—N1—C11—C12	89.6 (3)
C1A—Cr1—C1C—O1C	12 (4)	Cr1—N1—C11—C12	−83.2 (2)
C1E—Cr1—C1C—O1C	99 (4)	C16—C11—C12—C13	1.1 (3)
C1D—Cr1—C1C—O1C	−77 (4)	N1—C11—C12—C13	177.7 (2)
C1B—Cr1—C1C—O1C	−8 (5)	C11—C12—C13—C14	−0.4 (4)
N1—Cr1—C1C—O1C	−169 (4)	C12—C13—C14—C15	0.1 (4)
C1A—Cr1—C1D—O1D	−28 (2)	C13—C14—C15—C16	−0.5 (4)
C1C—Cr1—C1D—O1D	61 (2)	C14—C15—C16—C11	1.3 (4)
C1E—Cr1—C1D—O1D	6 (3)	C12—C11—C16—C15	−1.6 (3)
C1B—Cr1—C1D—O1D	−116 (2)	N1—C11—C16—C15	−178.1 (2)
N1—Cr1—C1D—O1D	150 (2)	N1—C2—C21—C22	−165.9 (2)
C1A—Cr1—C1E—O1E	41 (2)	N1—C2—C21—C26	12.5 (4)
C1C—Cr1—C1E—O1E	−48 (2)	C26—C21—C22—C23	−1.8 (3)
C1D—Cr1—C1E—O1E	7 (3)	C2—C21—C22—C23	176.7 (2)
C1B—Cr1—C1E—O1E	130 (2)	C21—C22—C23—C24	0.9 (3)
N1—Cr1—C1E—O1E	−136 (2)	C22—C23—C24—C25	0.9 (3)
C1A—Cr1—N1—C2	−49 (2)	C23—C24—C25—C26	−1.9 (4)
C1C—Cr1—N1—C2	−73.40 (19)	C24—C25—C26—C21	0.9 (3)
C1E—Cr1—N1—C2	15.86 (19)	C22—C21—C26—C25	0.9 (3)
C1D—Cr1—N1—C2	−161.31 (19)	C2—C21—C26—C25	−177.4 (2)
C1B—Cr1—N1—C2	107.58 (19)