Penta­carbon­yl[meth­yl(n-propyl­sulfan­yl)carbene]chromium(0)

The title compound, [Cr(C₅H₁₀S)(CO)₅], comprises a meth­yl(n-propyl­sulfan­yl)carbene ligand coordinated to a penta­carbonyl­chromium fragment, with the Cr atom in an octa­hedral coordination.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.077
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   C4      ..       5.52 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr1    -   C2      ..       8.67 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr1    -   C3      ..       7.38 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr1    -   C4      ..       9.58 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr1    -   C5      ..       9.25 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr1    -   C6      ..       8.70 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cr1    -   C11     ..       5.99 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: MWE and JE are students both involved in synthesis of the title compound. ES and UEIH are students involved in solving the crystal structure. HGR is the supervisor of all of the above, while CE is the crystallographer and author of the paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP for Windows (Farrugia, 1997); software used to prepare material for publication: X-SEED (Barbour, 2001).

Pentacarbonyl[methyl(n-propylsulfanyl)carbene]chromium(0)

Crystal data

[Cr(C5H10S)(CO)5]	Z = 2
Mr = 294.24	F(000) = 300
Triclinic, P1	Dx = 1.546 Mg m^−3
a = 6.1320 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4685 (9) Å	Cell parameters from 3334 reflections
c = 12.6187 (14) Å	θ = 2.5–26.8°
α = 77.264 (2)°	µ = 1.07 mm^−1
β = 81.530 (2)°	T = 173 K
γ = 87.878 (2)°	Needle, dark red
V = 632.17 (12) Å^3	0.30 × 0.10 × 0.10 mm

Data collection

Bruker APEX CCD area-detector diffractometer	2661 independent reflections
Radiation source: fine-focus sealed tube	2434 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω scans	θmax = 26.8°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.764, Tmax = 0.900	k = −10→10
6077 measured reflections	l = −15→15

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0352P)^2 + 0.4906P] where P = (Fo^2 + 2Fc^2)/3
2661 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.25 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	0.67779 (5)	0.77155 (3)	0.69137 (2)	0.01307 (10)
S11	0.90792 (8)	0.50686 (6)	0.86126 (4)	0.01865 (13)
C13	1.0342 (3)	0.3066 (2)	0.89046 (16)	0.0186 (4)
H13A	1.0066	0.2616	0.9706	0.022*
H13B	0.9626	0.2344	0.8541	0.022*
O4	0.9930 (2)	0.82533 (17)	0.47582 (12)	0.0242 (3)
O2	0.3833 (2)	0.71068 (18)	0.91198 (12)	0.0238 (3)
O6	0.4630 (3)	1.09912 (18)	0.61733 (12)	0.0281 (3)
O3	0.3520 (3)	0.60696 (19)	0.59040 (13)	0.0287 (4)
C5	0.8784 (3)	0.8767 (2)	0.75374 (16)	0.0189 (4)
O5	0.9950 (3)	0.94255 (19)	0.79162 (14)	0.0316 (4)
C4	0.8750 (3)	0.8043 (2)	0.55667 (16)	0.0176 (4)
C2	0.4906 (3)	0.7344 (2)	0.82814 (16)	0.0168 (4)
C15	1.3835 (3)	0.1437 (2)	0.89515 (18)	0.0232 (4)
H15A	1.3580	0.1183	0.9756	0.035*
H15B	1.5424	0.1476	0.8695	0.035*
H15C	1.3164	0.0600	0.8679	0.035*
C3	0.4739 (3)	0.6682 (2)	0.62805 (16)	0.0183 (4)
C11	0.8242 (3)	0.5511 (2)	0.73709 (15)	0.0149 (4)
C6	0.5424 (3)	0.9748 (2)	0.64443 (16)	0.0187 (4)
C12	0.8577 (3)	0.4250 (2)	0.66936 (17)	0.0204 (4)
H12A	1.0079	0.3813	0.6701	0.031*
H12B	0.8359	0.4739	0.5937	0.031*
H12C	0.7514	0.3374	0.7000	0.031*
C14	1.2805 (3)	0.3070 (2)	0.85240 (19)	0.0254 (5)
H14A	1.3504	0.3918	0.8788	0.030*
H14B	1.3082	0.3333	0.7712	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr1	0.01300 (16)	0.01363 (16)	0.01188 (16)	0.00084 (11)	−0.00164 (11)	−0.00153 (11)
S11	0.0243 (3)	0.0171 (2)	0.0153 (2)	0.00752 (19)	−0.00593 (19)	−0.00446 (18)
C13	0.0215 (10)	0.0145 (9)	0.0183 (9)	0.0048 (7)	−0.0029 (8)	−0.0008 (7)
O4	0.0272 (8)	0.0227 (7)	0.0203 (8)	−0.0008 (6)	0.0057 (6)	−0.0055 (6)
O2	0.0240 (8)	0.0249 (8)	0.0200 (8)	0.0006 (6)	0.0033 (6)	−0.0042 (6)
O6	0.0317 (9)	0.0241 (8)	0.0253 (8)	0.0092 (7)	−0.0054 (7)	0.0009 (6)
O3	0.0281 (8)	0.0325 (8)	0.0272 (8)	−0.0061 (7)	−0.0112 (7)	−0.0041 (7)
C5	0.0213 (10)	0.0164 (9)	0.0173 (10)	0.0026 (8)	−0.0022 (8)	−0.0008 (8)
O5	0.0326 (9)	0.0292 (8)	0.0370 (9)	−0.0060 (7)	−0.0134 (7)	−0.0092 (7)
C4	0.0204 (10)	0.0131 (9)	0.0200 (10)	0.0015 (7)	−0.0049 (8)	−0.0041 (7)
C2	0.0168 (9)	0.0142 (9)	0.0194 (10)	0.0022 (7)	−0.0042 (8)	−0.0031 (7)
C15	0.0199 (10)	0.0194 (10)	0.0306 (11)	0.0044 (8)	−0.0074 (9)	−0.0043 (8)
C3	0.0169 (10)	0.0198 (10)	0.0159 (9)	0.0015 (8)	−0.0020 (8)	0.0001 (8)
C11	0.0116 (9)	0.0180 (9)	0.0139 (9)	−0.0018 (7)	0.0005 (7)	−0.0019 (7)
C6	0.0182 (10)	0.0228 (10)	0.0137 (9)	−0.0003 (8)	−0.0012 (7)	−0.0018 (8)
C12	0.0230 (10)	0.0193 (10)	0.0211 (10)	0.0031 (8)	−0.0061 (8)	−0.0080 (8)
C14	0.0185 (10)	0.0192 (10)	0.0353 (12)	0.0025 (8)	−0.0035 (9)	0.0002 (9)

Geometric parameters (Å, º)

Cr1—C6	1.895 (2)	O6—C6	1.147 (2)
Cr1—C2	1.897 (2)	O3—C3	1.138 (2)
Cr1—C5	1.898 (2)	C5—O5	1.139 (3)
Cr1—C4	1.908 (2)	C15—C14	1.520 (3)
Cr1—C3	1.911 (2)	C15—H15A	0.9800
Cr1—C11	2.0442 (19)	C15—H15B	0.9800
S11—C11	1.6802 (19)	C15—H15C	0.9800
S11—C13	1.8229 (19)	C11—C12	1.499 (3)
C13—C14	1.516 (3)	C12—H12A	0.9800
C13—H13A	0.9900	C12—H12B	0.9800
C13—H13B	0.9900	C12—H12C	0.9800
O4—C4	1.144 (2)	C14—H14A	0.9900
O2—C2	1.142 (2)	C14—H14B	0.9900
C6—Cr1—C2	91.42 (8)	O2—C2—Cr1	177.97 (17)
C6—Cr1—C5	88.79 (8)	C14—C15—H15A	109.5
C2—Cr1—C5	88.77 (8)	C14—C15—H15B	109.5
C6—Cr1—C4	90.49 (8)	H15A—C15—H15B	109.5
C2—Cr1—C4	177.74 (8)	C14—C15—H15C	109.5
C5—Cr1—C4	90.07 (8)	H15A—C15—H15C	109.5
C6—Cr1—C3	90.47 (8)	H15B—C15—H15C	109.5
C2—Cr1—C3	91.22 (8)	O3—C3—Cr1	179.8 (2)
C5—Cr1—C3	179.26 (8)	C12—C11—S11	117.75 (14)
C4—Cr1—C3	89.98 (8)	C12—C11—Cr1	124.96 (13)
C6—Cr1—C11	178.18 (8)	Cr1—C11—S11	117.27 (10)
C2—Cr1—C11	89.98 (8)	O6—C6—Cr1	178.59 (18)
C5—Cr1—C11	92.40 (8)	C11—C12—H12A	109.5
C4—Cr1—C11	88.14 (8)	C11—C12—H12B	109.5
C3—Cr1—C11	88.34 (8)	H12A—C12—H12B	109.5
C11—S11—C13	112.20 (9)	C11—C12—H12C	109.5
C14—C13—S11	113.43 (14)	H12A—C12—H12C	109.5
C14—C13—H13A	108.9	H12B—C12—H12C	109.5
S11—C13—H13A	108.9	C13—C14—C15	111.23 (17)
C14—C13—H13B	108.9	C13—C14—H14A	109.4
S11—C13—H13B	108.9	C15—C14—H14A	109.4
H13A—C13—H13B	107.7	C13—C14—H14B	109.4
O5—C5—Cr1	178.36 (18)	C15—C14—H14B	109.4
O4—C4—Cr1	179.38 (17)	H14A—C14—H14B	108.0
C11—S11—C13—C14	89.24 (17)	S11—C11—Cr1—C5	39.70 (12)
C13—S11—C11—C12	1.15 (18)	S11—C11—Cr1—C4	129.69 (11)
C13—S11—C11—Cr1	179.85 (9)	S11—C11—Cr1—C3	−140.28 (11)
S11—C13—C14—C15	170.53 (15)	S11—C11—Cr1—C2	−49.06 (11)