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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021469/ob6297sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021469/ob6297Isup2.hkl
Contains datablock I

CCDC reference: 226641

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

Computing details top

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) top
Crystal data top
[Cr(C6H6FN)(CO)3]Dx = 1.729 Mg m3
Mr = 247.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 5835 reflections
a = 12.6648 (8) Åθ = 2.2–28.1°
b = 9.1249 (5) ŵ = 1.20 mm1
c = 8.2136 (5) ÅT = 298 K
V = 949.20 (10) Å3Needle, yellow
Z = 40.66 × 0.27 × 0.12 mm
F(000) = 496
Data collection top
Bruker SMART APEX CCD
diffractometer
1185 independent reflections
Radiation source: fine-focus sealed tube1122 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 28.2°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 1997)
h = 1616
Tmin = 0.728, Tmax = 0.870k = 1112
7436 measured reflectionsl = 1010
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077All H-atom parameters refined
S = 1.08 w = 1/[σ2(Fo2) + (0.046P)2 + 0.2515P]
where P = (Fo2 + 2Fc2)/3
1185 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.32 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
Cr10.10254 (2)0.25000.44896 (4)0.03401 (14)
F10.35070 (13)0.25000.3517 (2)0.0830 (6)
O20.06001 (11)0.03632 (15)0.18227 (15)0.0616 (3)
O10.12710 (16)0.25000.5386 (3)0.0699 (6)
C40.13421 (19)0.25000.7309 (3)0.0456 (5)
C60.07699 (12)0.11588 (17)0.28890 (18)0.0413 (3)
N10.0726 (2)0.25000.8670 (3)0.0612 (6)
C50.03940 (18)0.25000.5043 (3)0.0445 (5)
C20.23866 (14)0.1175 (2)0.5282 (2)0.0525 (4)
C30.16520 (13)0.11699 (19)0.65780 (19)0.0472 (4)
C10.27675 (18)0.25000.4715 (3)0.0551 (6)
H30.1378 (15)0.032 (2)0.695 (2)0.047 (4)*
H20.2586 (15)0.034 (2)0.488 (3)0.057 (5)*
H10.0412 (19)0.171 (2)0.897 (3)0.072 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.0344 (2)0.0387 (2)0.0289 (2)0.0000.00022 (10)0.000
F10.0495 (9)0.1219 (16)0.0777 (12)0.0000.0247 (8)0.000
O20.0711 (8)0.0625 (7)0.0511 (7)0.0031 (7)0.0004 (6)0.0193 (6)
O10.0424 (9)0.0946 (17)0.0727 (14)0.0000.0094 (8)0.000
C40.0493 (11)0.0578 (12)0.0297 (10)0.0000.0048 (9)0.000
C60.0422 (7)0.0445 (7)0.0371 (7)0.0013 (6)0.0014 (6)0.0006 (6)
N10.0813 (16)0.0682 (15)0.0340 (10)0.0000.0104 (10)0.000
C50.0435 (11)0.0526 (12)0.0374 (10)0.0000.0001 (9)0.000
C20.0457 (9)0.0637 (11)0.0483 (9)0.0171 (8)0.0045 (6)0.0024 (8)
C30.0528 (8)0.0495 (9)0.0393 (8)0.0061 (7)0.0064 (6)0.0075 (6)
C10.0343 (11)0.0833 (18)0.0479 (13)0.0000.0024 (9)0.000
Geometric parameters (Å, º) top
Cr1—C61.8250 (15)O1—C51.146 (3)
Cr1—C6i1.8250 (15)C4—N11.363 (3)
Cr1—C51.854 (2)C4—C31.410 (2)
Cr1—C2i2.2040 (17)C4—C3i1.410 (2)
Cr1—C22.2040 (17)N1—H10.86 (2)
Cr1—C12.214 (2)C2—C11.383 (2)
Cr1—C3i2.2462 (15)C2—C31.414 (2)
Cr1—C32.2462 (15)C2—H20.87 (2)
Cr1—C42.350 (2)C3—H30.902 (19)
F1—C11.358 (3)C1—C2i1.383 (2)
O2—C61.1577 (19)
C6—Cr1—C6i84.22 (10)C2—Cr1—C464.89 (6)
C6—Cr1—C590.28 (7)C1—Cr1—C475.38 (9)
C6i—Cr1—C590.28 (7)C3i—Cr1—C435.63 (5)
C6—Cr1—C2i136.00 (7)C3—Cr1—C435.63 (5)
C6i—Cr1—C2i89.05 (7)N1—C4—C3120.57 (10)
C5—Cr1—C2i133.30 (7)N1—C4—C3i120.57 (10)
C6—Cr1—C289.05 (7)C3—C4—C3i118.8 (2)
C6i—Cr1—C2136.00 (7)N1—C4—Cr1135.24 (19)
C5—Cr1—C2133.30 (7)C3—C4—Cr168.15 (10)
C2i—Cr1—C266.56 (11)C3i—C4—Cr168.15 (10)
C6—Cr1—C1103.70 (7)O2—C6—Cr1176.72 (14)
C6i—Cr1—C1103.70 (7)C4—N1—H1119.8 (16)
C5—Cr1—C1161.01 (10)O1—C5—Cr1180.0 (2)
C2i—Cr1—C136.48 (6)C1—C2—C3119.06 (18)
C2—Cr1—C136.48 (6)C1—C2—Cr172.16 (12)
C6—Cr1—C3i167.19 (7)C3—C2—Cr173.10 (9)
C6i—Cr1—C3i104.50 (6)C1—C2—H2122.6 (14)
C5—Cr1—C3i98.92 (8)C3—C2—H2118.3 (14)
C2i—Cr1—C3i37.04 (6)Cr1—C2—H2126.7 (14)
C2—Cr1—C3i78.16 (7)C4—C3—C2120.08 (17)
C1—Cr1—C3i65.43 (7)C4—C3—Cr176.22 (10)
C6—Cr1—C3104.50 (6)C2—C3—Cr169.86 (9)
C6i—Cr1—C3167.19 (7)C4—C3—H3119.3 (12)
C5—Cr1—C398.92 (7)C2—C3—H3120.6 (12)
C2i—Cr1—C378.16 (7)Cr1—C3—H3125.9 (13)
C2—Cr1—C337.04 (6)F1—C1—C2118.98 (11)
C1—Cr1—C365.43 (7)F1—C1—C2i118.98 (11)
C3i—Cr1—C365.42 (9)C2—C1—C2i122.0 (2)
C6—Cr1—C4137.73 (5)F1—C1—Cr1128.79 (18)
C6i—Cr1—C4137.73 (5)C2—C1—Cr171.37 (11)
C5—Cr1—C485.63 (9)C2i—C1—Cr171.37 (11)
C2i—Cr1—C464.89 (6)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2ii0.86 (2)2.38 (2)3.132 (2)147 (2)
N1—H1···O2iii0.86 (2)2.66 (2)3.245 (2)127 (2)
Symmetry codes: (ii) x, y, z+1; (iii) x, y, z+1.
 

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