Tetra­carbon­yl(tricyclo­hexyl­phosphine)iron(0)

The coordination of the Fe atom in the title compound, [Fe(P(C₆H₁₁)₃(CO)₄], is trigonal biypramidal, with the phosphine ligand adopting one of the axial positions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.099
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      23.27 Deg.

Author Response: The value is only slightly below the criterion for MoKa. In addition, the data parameter ratio looks alright.

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93

Author Response: cf. response to _vrf_PLAT027_io696

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5559

Author Response: cf. response to _vrf_PLAT027_io696

PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      23.27 Deg.

Author Response: cf. response to _vrf_PLAT027_io696

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           23.27
           From the CIF: _diffrn_reflns_theta_full          23.27
           From the CIF: _reflns_number_total               3142
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3363
           Completeness (_total/calc)             93.43%

Author Response: cf. response to _vrf_PLAT027_io696

PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93

Author Response: cf. response to _vrf_REFLT03_io696

PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K

Author Response: This was indeed a mesurement done at room temperature.

PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

Author Response: This was indeed a mesurement done at room temperature.

PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio

Author Response: Due to the data collection at room temperature some carbon atoms of the cyclohexyl moieties show high Ueqs. Nevertheless, it was not possible to refine this in terms of disordered conformations.

PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   C21     ..       5.33 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.948
            Tmax scaled      0.863 Tmin scaled      0.783

   2 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 (de Boer et al., 1984); data reduction: MolEN (Enraf–Nonius, 1990); 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: SHELXL97.

Tetracarbonyl(tricyclohexylphosphine)iron(0)

Crystal data

[Fe(C18H33P)(CO)4]	F(000) = 952
Mr = 448.30	Dx = 1.273 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 25 reflections
a = 13.8477 (6) Å	θ = 15.6–26.2°
b = 9.9505 (4) Å	µ = 0.74 mm^−1
c = 17.0330 (3) Å	T = 293 K
β = 94.432 (3)°	Block, yellow
V = 2339.99 (14) Å^3	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	2771 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 23.3°, θmin = 3.6°
ω/2θ scans	h = −14→14
Absorption correction: ψ scan (North et al., 1968)	k = −11→0
Tmin = 0.826, Tmax = 0.910	l = −18→18
6062 measured reflections	3 standard reflections every 60 min
3142 independent reflections	intensity decay: 0.8%

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0375P)^2 + 0.9945P] where P = (Fo^2 + 2Fc^2)/3
3142 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.26 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
Fe1	0.26552 (3)	0.12457 (4)	0.969236 (19)	0.05746 (17)
P1	0.27012 (4)	0.25537 (6)	1.08024 (3)	0.04555 (19)
C1	0.39487 (18)	0.2569 (3)	1.13094 (14)	0.0590 (6)
H1	0.4129	0.1618	1.1359	0.089*
C2	0.4704 (2)	0.3177 (5)	1.08223 (19)	0.0963 (11)
H2A	0.4605	0.4140	1.0783	0.144*
H2B	0.4636	0.2804	1.0295	0.144*
C3	0.5723 (3)	0.2889 (6)	1.1196 (2)	0.1261 (16)
H3A	0.5844	0.1930	1.1173	0.189*
H3B	0.6191	0.3336	1.0890	0.189*
C4	0.5869 (2)	0.3336 (4)	1.2021 (2)	0.0971 (11)
H4A	0.5837	0.4310	1.2041	0.146*
H4B	0.6507	0.3062	1.2238	0.146*
C5	0.5121 (3)	0.2755 (5)	1.2503 (2)	0.1199 (15)
H5A	0.5206	0.3108	1.3035	0.180*
H5B	0.5196	0.1787	1.2530	0.180*
C6	0.4083 (2)	0.3109 (5)	1.21352 (18)	0.1056 (13)
H6A	0.3602	0.2720	1.2452	0.158*
H6B	0.3997	0.4076	1.2128	0.158*
C7	0.19364 (17)	0.1991 (2)	1.15872 (13)	0.0490 (5)
H7	0.2111	0.2559	1.2046	0.074*
C8	0.2155 (2)	0.0537 (3)	1.18493 (16)	0.0631 (7)
H8A	0.1969	−0.0071	1.1418	0.095*
H8B	0.2846	0.0437	1.1980	0.095*
C9	0.1611 (2)	0.0163 (3)	1.25623 (17)	0.0782 (8)
H9A	0.1737	−0.0771	1.2697	0.117*
H9B	0.1846	0.0709	1.3008	0.117*
C10	0.0531 (2)	0.0370 (3)	1.2404 (2)	0.0823 (9)
H10A	0.0212	0.0187	1.2880	0.123*
H10B	0.0280	−0.0253	1.2001	0.123*
C11	0.0313 (3)	0.1803 (4)	1.2136 (2)	0.0942 (11)
H11A	0.0510	0.2421	1.2559	0.141*
H11B	−0.0378	0.1906	1.2013	0.141*
C12	0.0850 (2)	0.2147 (3)	1.14083 (19)	0.0774 (8)
H12A	0.0632	0.1557	1.0977	0.116*
H12B	0.0704	0.3065	1.1248	0.116*
C13	0.2399 (2)	0.4353 (2)	1.06064 (15)	0.0582 (6)
H13	0.2981	0.4733	1.0400	0.087*
C14	0.2230 (3)	0.5207 (3)	1.13260 (18)	0.0853 (9)
H14A	0.2755	0.5062	1.1728	0.128*
H14B	0.1632	0.4928	1.1539	0.128*
C15	0.2170 (4)	0.6704 (3)	1.1120 (3)	0.1238 (16)
H15A	0.2015	0.7209	1.1581	0.186*
H15B	0.2795	0.7008	1.0971	0.186*
C16	0.1418 (3)	0.6975 (3)	1.0460 (2)	0.1056 (12)
H16A	0.1446	0.7915	1.0314	0.158*
H16B	0.0781	0.6803	1.0640	0.158*
C17	0.1551 (3)	0.6122 (3)	0.9745 (2)	0.0896 (10)
H17A	0.2145	0.6379	0.9518	0.134*
H17B	0.1016	0.6274	0.9353	0.134*
C18	0.1596 (2)	0.4604 (3)	0.99672 (18)	0.0781 (8)
H18A	0.0981	0.4326	1.0151	0.117*
H18B	0.1712	0.4075	0.9505	0.117*
C19	0.1374 (3)	0.1232 (4)	0.9602 (2)	0.0895 (10)
O1	0.0549 (2)	0.1180 (4)	0.9474 (2)	0.1527 (14)
C20	0.2584 (3)	0.0209 (3)	0.88426 (18)	0.0834 (9)
O2	0.2508 (2)	−0.0459 (3)	0.82919 (14)	0.1269 (10)
C21	0.3381 (2)	0.0010 (3)	1.02191 (15)	0.0681 (7)
O3	0.38747 (19)	−0.0800 (2)	1.05253 (14)	0.0969 (7)
C22	0.3259 (3)	0.2548 (3)	0.92125 (16)	0.0774 (9)
O4	0.3641 (2)	0.3383 (3)	0.88847 (15)	0.1166 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0683 (3)	0.0607 (3)	0.0431 (2)	0.00926 (17)	0.00240 (17)	−0.00448 (15)
P1	0.0475 (4)	0.0468 (4)	0.0422 (3)	0.0006 (2)	0.0029 (2)	0.0014 (2)
C1	0.0514 (16)	0.0683 (16)	0.0563 (14)	−0.0054 (11)	−0.0032 (11)	0.0033 (12)
C2	0.058 (2)	0.158 (3)	0.0731 (19)	−0.020 (2)	0.0076 (14)	0.003 (2)
C3	0.049 (2)	0.212 (5)	0.117 (3)	−0.009 (2)	0.0039 (19)	−0.022 (3)
C4	0.059 (2)	0.120 (3)	0.109 (3)	−0.0174 (18)	−0.0145 (18)	−0.004 (2)
C5	0.084 (3)	0.189 (4)	0.080 (2)	−0.038 (3)	−0.0323 (19)	0.016 (3)
C6	0.067 (2)	0.191 (4)	0.0579 (18)	−0.030 (2)	−0.0035 (15)	−0.017 (2)
C7	0.0522 (14)	0.0483 (13)	0.0470 (12)	−0.0016 (10)	0.0061 (10)	−0.0015 (10)
C8	0.0648 (17)	0.0623 (16)	0.0634 (15)	0.0056 (12)	0.0127 (12)	0.0163 (13)
C9	0.084 (2)	0.084 (2)	0.0684 (18)	−0.0039 (16)	0.0165 (15)	0.0229 (15)
C10	0.082 (2)	0.078 (2)	0.090 (2)	−0.0092 (16)	0.0310 (17)	0.0138 (16)
C11	0.070 (2)	0.088 (2)	0.130 (3)	0.0075 (17)	0.0459 (19)	0.025 (2)
C12	0.0559 (18)	0.0788 (19)	0.099 (2)	0.0080 (14)	0.0156 (15)	0.0279 (17)
C13	0.0713 (17)	0.0455 (13)	0.0577 (14)	0.0027 (11)	0.0044 (12)	0.0091 (11)
C14	0.133 (3)	0.0532 (16)	0.0687 (18)	0.0099 (17)	0.0002 (18)	−0.0074 (14)
C15	0.184 (4)	0.0508 (18)	0.131 (3)	0.013 (2)	−0.028 (3)	−0.007 (2)
C16	0.118 (3)	0.061 (2)	0.135 (3)	0.0265 (19)	−0.006 (2)	0.006 (2)
C17	0.097 (3)	0.077 (2)	0.093 (2)	0.0269 (17)	−0.0033 (18)	0.0232 (18)
C18	0.083 (2)	0.0713 (19)	0.0771 (19)	0.0204 (15)	−0.0089 (15)	0.0037 (15)
C19	0.073 (2)	0.112 (3)	0.081 (2)	0.0090 (18)	−0.0088 (17)	−0.0395 (18)
O1	0.078 (2)	0.212 (4)	0.163 (3)	0.0099 (19)	−0.0234 (18)	−0.095 (3)
C20	0.111 (3)	0.084 (2)	0.0543 (17)	0.0215 (18)	−0.0004 (15)	−0.0122 (16)
O2	0.182 (3)	0.125 (2)	0.0702 (15)	0.0309 (19)	−0.0094 (16)	−0.0401 (16)
C21	0.086 (2)	0.0637 (17)	0.0543 (15)	0.0116 (15)	0.0033 (13)	−0.0079 (13)
O3	0.1211 (19)	0.0796 (14)	0.0874 (15)	0.0349 (14)	−0.0081 (13)	0.0029 (12)
C22	0.107 (3)	0.079 (2)	0.0489 (15)	0.0077 (17)	0.0178 (15)	0.0031 (14)
O4	0.169 (3)	0.1064 (18)	0.0788 (16)	−0.0166 (18)	0.0369 (16)	0.0213 (14)

Geometric parameters (Å, º)

Fe1—C19	1.769 (4)	C9—H9A	0.9700
Fe1—C20	1.774 (3)	C9—H9B	0.9700
Fe1—C22	1.776 (3)	C10—C11	1.521 (4)
Fe1—C21	1.785 (3)	C10—H10A	0.9700
Fe1—P1	2.2922 (7)	C10—H10B	0.9700
P1—C7	1.855 (2)	C11—C12	1.533 (4)
P1—C13	1.863 (2)	C11—H11A	0.9700
P1—C1	1.871 (2)	C11—H11B	0.9700
C1—C6	1.504 (4)	C12—H12A	0.9700
C1—C2	1.511 (4)	C12—H12B	0.9700
C1—H1	0.9800	C13—C18	1.515 (4)
C2—C3	1.529 (5)	C13—C14	1.524 (4)
C2—H2A	0.9700	C13—H13	0.9800
C2—H2B	0.9700	C14—C15	1.531 (4)
C3—C4	1.473 (5)	C14—H14A	0.9700
C3—H3A	0.9700	C14—H14B	0.9700
C3—H3B	0.9700	C15—C16	1.497 (6)
C4—C5	1.488 (5)	C15—H15A	0.9700
C4—H4A	0.9700	C15—H15B	0.9700
C4—H4B	0.9700	C16—C17	1.507 (5)
C5—C6	1.562 (5)	C16—H16A	0.9700
C5—H5A	0.9700	C16—H16B	0.9700
C5—H5B	0.9700	C17—C18	1.557 (4)
C6—H6A	0.9700	C17—H17A	0.9700
C6—H6B	0.9700	C17—H17B	0.9700
C7—C12	1.520 (4)	C18—H18A	0.9700
C7—C8	1.537 (3)	C18—H18B	0.9700
C7—H7	0.9800	C19—O1	1.147 (4)
C8—C9	1.524 (4)	C20—O2	1.148 (4)
C8—H8A	0.9700	C21—O3	1.155 (3)
C8—H8B	0.9700	C22—O4	1.152 (4)
C9—C10	1.512 (4)
C19—Fe1—C20	86.14 (15)	C10—C9—C8	111.6 (2)
C19—Fe1—C22	118.09 (17)	C10—C9—H9A	109.3
C20—Fe1—C22	92.69 (15)	C8—C9—H9A	109.3
C19—Fe1—C21	124.03 (17)	C10—C9—H9B	109.3
C20—Fe1—C21	90.18 (13)	C8—C9—H9B	109.3
C22—Fe1—C21	117.86 (15)	H9A—C9—H9B	108.0
C19—Fe1—P1	92.29 (10)	C9—C10—C11	110.6 (3)
C20—Fe1—P1	178.14 (12)	C9—C10—H10A	109.5
C22—Fe1—P1	88.93 (9)	C11—C10—H10A	109.5
C21—Fe1—P1	89.88 (8)	C9—C10—H10B	109.5
C7—P1—C13	106.66 (11)	C11—C10—H10B	109.5
C7—P1—C1	103.17 (11)	H10A—C10—H10B	108.1
C13—P1—C1	105.18 (12)	C10—C11—C12	110.8 (3)
C7—P1—Fe1	116.22 (8)	C10—C11—H11A	109.5
C13—P1—Fe1	113.98 (8)	C12—C11—H11A	109.5
C1—P1—Fe1	110.55 (9)	C10—C11—H11B	109.5
C6—C1—C2	109.2 (2)	C12—C11—H11B	109.5
C6—C1—P1	118.5 (2)	H11A—C11—H11B	108.1
C2—C1—P1	113.78 (19)	C7—C12—C11	110.4 (3)
C6—C1—H1	104.6	C7—C12—H12A	109.6
C2—C1—H1	104.6	C11—C12—H12A	109.6
P1—C1—H1	104.6	C7—C12—H12B	109.6
C1—C2—C3	110.6 (3)	C11—C12—H12B	109.6
C1—C2—H2A	109.5	H12A—C12—H12B	108.1
C3—C2—H2A	109.5	C18—C13—C14	109.6 (2)
C1—C2—H2B	109.5	C18—C13—P1	115.44 (19)
C3—C2—H2B	109.5	C14—C13—P1	115.98 (18)
H2A—C2—H2B	108.1	C18—C13—H13	104.8
C4—C3—C2	113.3 (3)	C14—C13—H13	104.8
C4—C3—H3A	108.9	P1—C13—H13	104.8
C2—C3—H3A	108.9	C13—C14—C15	111.6 (3)
C4—C3—H3B	108.9	C13—C14—H14A	109.3
C2—C3—H3B	108.9	C15—C14—H14A	109.3
H3A—C3—H3B	107.7	C13—C14—H14B	109.3
C3—C4—C5	111.0 (3)	C15—C14—H14B	109.3
C3—C4—H4A	109.4	H14A—C14—H14B	108.0
C5—C4—H4A	109.4	C16—C15—C14	111.7 (3)
C3—C4—H4B	109.4	C16—C15—H15A	109.3
C5—C4—H4B	109.4	C14—C15—H15A	109.3
H4A—C4—H4B	108.0	C16—C15—H15B	109.3
C4—C5—C6	110.4 (3)	C14—C15—H15B	109.3
C4—C5—H5A	109.6	H15A—C15—H15B	107.9
C6—C5—H5A	109.6	C15—C16—C17	112.6 (3)
C4—C5—H5B	109.6	C15—C16—H16A	109.1
C6—C5—H5B	109.6	C17—C16—H16A	109.1
H5A—C5—H5B	108.1	C15—C16—H16B	109.1
C1—C6—C5	109.8 (3)	C17—C16—H16B	109.1
C1—C6—H6A	109.7	H16A—C16—H16B	107.8
C5—C6—H6A	109.7	C16—C17—C18	110.8 (3)
C1—C6—H6B	109.7	C16—C17—H17A	109.5
C5—C6—H6B	109.7	C18—C17—H17A	109.5
H6A—C6—H6B	108.2	C16—C17—H17B	109.5
C12—C7—C8	109.0 (2)	C18—C17—H17B	109.5
C12—C7—P1	115.84 (17)	H17A—C17—H17B	108.1
C8—C7—P1	112.50 (16)	C13—C18—C17	110.4 (3)
C12—C7—H7	106.3	C13—C18—H18A	109.6
C8—C7—H7	106.3	C17—C18—H18A	109.6
P1—C7—H7	106.3	C13—C18—H18B	109.6
C9—C8—C7	111.2 (2)	C17—C18—H18B	109.6
C9—C8—H8A	109.4	H18A—C18—H18B	108.1
C7—C8—H8A	109.4	O1—C19—Fe1	173.6 (3)
C9—C8—H8B	109.4	O2—C20—Fe1	177.9 (3)
C7—C8—H8B	109.4	O3—C21—Fe1	176.5 (3)
H8A—C8—H8B	108.0	O4—C22—Fe1	178.4 (3)