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
CCDC reference: 226641
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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 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) Å3 | Needle, yellow |
Z = 4 | 0.66 × 0.27 × 0.12 mm |
F(000) = 496 | |
Data collection top
Bruker SMART APEX CCD diffractometer | 1185 independent reflections |
Radiation source: fine-focus sealed 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 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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | All 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 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.32 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 | |
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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Cr1—C6 | 1.8250 (15) | O1—C5 | 1.146 (3) |
Cr1—C6i | 1.8250 (15) | C4—N1 | 1.363 (3) |
Cr1—C5 | 1.854 (2) | C4—C3 | 1.410 (2) |
Cr1—C2i | 2.2040 (17) | C4—C3i | 1.410 (2) |
Cr1—C2 | 2.2040 (17) | N1—H1 | 0.86 (2) |
Cr1—C1 | 2.214 (2) | C2—C1 | 1.383 (2) |
Cr1—C3i | 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—C2i | 1.383 (2) |
O2—C6 | 1.1577 (19) | | |
| | | |
C6—Cr1—C6i | 84.22 (10) | C2—Cr1—C4 | 64.89 (6) |
C6—Cr1—C5 | 90.28 (7) | C1—Cr1—C4 | 75.38 (9) |
C6i—Cr1—C5 | 90.28 (7) | C3i—Cr1—C4 | 35.63 (5) |
C6—Cr1—C2i | 136.00 (7) | C3—Cr1—C4 | 35.63 (5) |
C6i—Cr1—C2i | 89.05 (7) | N1—C4—C3 | 120.57 (10) |
C5—Cr1—C2i | 133.30 (7) | N1—C4—C3i | 120.57 (10) |
C6—Cr1—C2 | 89.05 (7) | C3—C4—C3i | 118.8 (2) |
C6i—Cr1—C2 | 136.00 (7) | N1—C4—Cr1 | 135.24 (19) |
C5—Cr1—C2 | 133.30 (7) | C3—C4—Cr1 | 68.15 (10) |
C2i—Cr1—C2 | 66.56 (11) | C3i—C4—Cr1 | 68.15 (10) |
C6—Cr1—C1 | 103.70 (7) | O2—C6—Cr1 | 176.72 (14) |
C6i—Cr1—C1 | 103.70 (7) | C4—N1—H1 | 119.8 (16) |
C5—Cr1—C1 | 161.01 (10) | O1—C5—Cr1 | 180.0 (2) |
C2i—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—C3i | 167.19 (7) | C3—C2—Cr1 | 73.10 (9) |
C6i—Cr1—C3i | 104.50 (6) | C1—C2—H2 | 122.6 (14) |
C5—Cr1—C3i | 98.92 (8) | C3—C2—H2 | 118.3 (14) |
C2i—Cr1—C3i | 37.04 (6) | Cr1—C2—H2 | 126.7 (14) |
C2—Cr1—C3i | 78.16 (7) | C4—C3—C2 | 120.08 (17) |
C1—Cr1—C3i | 65.43 (7) | C4—C3—Cr1 | 76.22 (10) |
C6—Cr1—C3 | 104.50 (6) | C2—C3—Cr1 | 69.86 (9) |
C6i—Cr1—C3 | 167.19 (7) | C4—C3—H3 | 119.3 (12) |
C5—Cr1—C3 | 98.92 (7) | C2—C3—H3 | 120.6 (12) |
C2i—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—C2i | 118.98 (11) |
C3i—Cr1—C3 | 65.42 (9) | C2—C1—C2i | 122.0 (2) |
C6—Cr1—C4 | 137.73 (5) | F1—C1—Cr1 | 128.79 (18) |
C6i—Cr1—C4 | 137.73 (5) | C2—C1—Cr1 | 71.37 (11) |
C5—Cr1—C4 | 85.63 (9) | C2i—C1—Cr1 | 71.37 (11) |
C2i—Cr1—C4 | 64.89 (6) | | |
Symmetry code: (i) x, −y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2ii | 0.86 (2) | 2.38 (2) | 3.132 (2) | 147 (2) |
N1—H1···O2iii | 0.86 (2) | 2.66 (2) | 3.245 (2) | 127 (2) |
Symmetry codes: (ii) −x, −y, −z+1; (iii) x, y, z+1. |