Tri­carbonyl(η⁶-4-fluoro­aniline)­chromium

The title compound, [Cr(C₆H₆FN)(CO)₃], exhibits the three-legged piano-stool structure expected for a metal tri­carbonyl with an η⁶-coordinated arene. A crystallographic mirror plane bisects the mol­ecule. The amine and fluoro­arene functional groups display an out-of-plane distortion.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.026
• wR factor = 0.076
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cr1    -   C6       =      10.36 su

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.66 mm
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...          2
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr1    -   C5       =       8.19 su

   1 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
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997-2000); cell refinement: SAINT-Plus (Bruker, 1997-1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(h6-p-fluoroaniline)chromium(tricarbonyl)

Crystal data

[Cr(C6H6FN)(CO)3]	Dx = 1.729 Mg m^−3
Mr = 247.15	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 5835 reflections
a = 12.6648 (8) Å	θ = 2.2–28.1°
b = 9.1249 (5) Å	µ = 1.20 mm^−1
c = 8.2136 (5) Å	T = 298 K
V = 949.20 (10) Å^3	Needle, yellow
Z = 4	0.66 × 0.27 × 0.12 mm
F(000) = 496

Data collection

Bruker SMART APEX CCD diffractometer	1185 independent reflections
Radiation source: fine-focus sealed tube	1122 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω scans	θmax = 28.2°, θmin = 3.0°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1997)	h = −16→16
Tmin = 0.728, Tmax = 0.870	k = −11→12
7436 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	All H-atom parameters refined
S = 1.08	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.2515P] where P = (Fo^2 + 2Fc^2)/3
1185 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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	0.10254 (2)	0.2500	0.44896 (4)	0.03401 (14)
F1	0.35070 (13)	0.2500	0.3517 (2)	0.0830 (6)
O2	0.06001 (11)	0.03632 (15)	0.18227 (15)	0.0616 (3)
O1	−0.12710 (16)	0.2500	0.5386 (3)	0.0699 (6)
C4	0.13421 (19)	0.2500	0.7309 (3)	0.0456 (5)
C6	0.07699 (12)	0.11588 (17)	0.28890 (18)	0.0413 (3)
N1	0.0726 (2)	0.2500	0.8670 (3)	0.0612 (6)
C5	−0.03940 (18)	0.2500	0.5043 (3)	0.0445 (5)
C2	0.23866 (14)	0.1175 (2)	0.5282 (2)	0.0525 (4)
C3	0.16520 (13)	0.11699 (19)	0.65780 (19)	0.0472 (4)
C1	0.27675 (18)	0.2500	0.4715 (3)	0.0551 (6)
H3	0.1378 (15)	0.032 (2)	0.695 (2)	0.047 (4)*
H2	0.2586 (15)	0.034 (2)	0.488 (3)	0.057 (5)*
H1	0.0412 (19)	0.171 (2)	0.897 (3)	0.072 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr1	0.0344 (2)	0.0387 (2)	0.0289 (2)	0.000	−0.00022 (10)	0.000
F1	0.0495 (9)	0.1219 (16)	0.0777 (12)	0.000	0.0247 (8)	0.000
O2	0.0711 (8)	0.0625 (7)	0.0511 (7)	−0.0031 (7)	0.0004 (6)	−0.0193 (6)
O1	0.0424 (9)	0.0946 (17)	0.0727 (14)	0.000	0.0094 (8)	0.000
C4	0.0493 (11)	0.0578 (12)	0.0297 (10)	0.000	−0.0048 (9)	0.000
C6	0.0422 (7)	0.0445 (7)	0.0371 (7)	0.0013 (6)	0.0014 (6)	−0.0006 (6)
N1	0.0813 (16)	0.0682 (15)	0.0340 (10)	0.000	0.0104 (10)	0.000
C5	0.0435 (11)	0.0526 (12)	0.0374 (10)	0.000	−0.0001 (9)	0.000
C2	0.0457 (9)	0.0637 (11)	0.0483 (9)	0.0171 (8)	−0.0045 (6)	−0.0024 (8)
C3	0.0528 (8)	0.0495 (9)	0.0393 (8)	0.0061 (7)	−0.0064 (6)	0.0075 (6)
C1	0.0343 (11)	0.0833 (18)	0.0479 (13)	0.000	0.0024 (9)	0.000

Geometric parameters (Å, º)

Cr1—C6	1.8250 (15)	O1—C5	1.146 (3)
Cr1—C6^i	1.8250 (15)	C4—N1	1.363 (3)
Cr1—C5	1.854 (2)	C4—C3	1.410 (2)
Cr1—C2^i	2.2040 (17)	C4—C3^i	1.410 (2)
Cr1—C2	2.2040 (17)	N1—H1	0.86 (2)
Cr1—C1	2.214 (2)	C2—C1	1.383 (2)
Cr1—C3^i	2.2462 (15)	C2—C3	1.414 (2)
Cr1—C3	2.2462 (15)	C2—H2	0.87 (2)
Cr1—C4	2.350 (2)	C3—H3	0.902 (19)
F1—C1	1.358 (3)	C1—C2^i	1.383 (2)
O2—C6	1.1577 (19)
C6—Cr1—C6^i	84.22 (10)	C2—Cr1—C4	64.89 (6)
C6—Cr1—C5	90.28 (7)	C1—Cr1—C4	75.38 (9)
C6^i—Cr1—C5	90.28 (7)	C3^i—Cr1—C4	35.63 (5)
C6—Cr1—C2^i	136.00 (7)	C3—Cr1—C4	35.63 (5)
C6^i—Cr1—C2^i	89.05 (7)	N1—C4—C3	120.57 (10)
C5—Cr1—C2^i	133.30 (7)	N1—C4—C3^i	120.57 (10)
C6—Cr1—C2	89.05 (7)	C3—C4—C3^i	118.8 (2)
C6^i—Cr1—C2	136.00 (7)	N1—C4—Cr1	135.24 (19)
C5—Cr1—C2	133.30 (7)	C3—C4—Cr1	68.15 (10)
C2^i—Cr1—C2	66.56 (11)	C3^i—C4—Cr1	68.15 (10)
C6—Cr1—C1	103.70 (7)	O2—C6—Cr1	176.72 (14)
C6^i—Cr1—C1	103.70 (7)	C4—N1—H1	119.8 (16)
C5—Cr1—C1	161.01 (10)	O1—C5—Cr1	180.0 (2)
C2^i—Cr1—C1	36.48 (6)	C1—C2—C3	119.06 (18)
C2—Cr1—C1	36.48 (6)	C1—C2—Cr1	72.16 (12)
C6—Cr1—C3^i	167.19 (7)	C3—C2—Cr1	73.10 (9)
C6^i—Cr1—C3^i	104.50 (6)	C1—C2—H2	122.6 (14)
C5—Cr1—C3^i	98.92 (8)	C3—C2—H2	118.3 (14)
C2^i—Cr1—C3^i	37.04 (6)	Cr1—C2—H2	126.7 (14)
C2—Cr1—C3^i	78.16 (7)	C4—C3—C2	120.08 (17)
C1—Cr1—C3^i	65.43 (7)	C4—C3—Cr1	76.22 (10)
C6—Cr1—C3	104.50 (6)	C2—C3—Cr1	69.86 (9)
C6^i—Cr1—C3	167.19 (7)	C4—C3—H3	119.3 (12)
C5—Cr1—C3	98.92 (7)	C2—C3—H3	120.6 (12)
C2^i—Cr1—C3	78.16 (7)	Cr1—C3—H3	125.9 (13)
C2—Cr1—C3	37.04 (6)	F1—C1—C2	118.98 (11)
C1—Cr1—C3	65.43 (7)	F1—C1—C2^i	118.98 (11)
C3^i—Cr1—C3	65.42 (9)	C2—C1—C2^i	122.0 (2)
C6—Cr1—C4	137.73 (5)	F1—C1—Cr1	128.79 (18)
C6^i—Cr1—C4	137.73 (5)	C2—C1—Cr1	71.37 (11)
C5—Cr1—C4	85.63 (9)	C2^i—C1—Cr1	71.37 (11)
C2^i—Cr1—C4	64.89 (6)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^ii	0.86 (2)	2.38 (2)	3.132 (2)	147 (2)
N1—H1···O2^iii	0.86 (2)	2.66 (2)	3.245 (2)	127 (2)

Symmetry codes: (ii) −x, −y, −z+1; (iii) x, y, z+1.