Bromo­tricarbon­yl{15-[2-(methyl­sulfan­yl)ethyl­sulfanyl]penta­deca­noic acid-κ²S,S′}rhenium(I)

The title compound, [ReBr(C₁₈H₃₆O₂S₂)(CO)₃], was synthesized and characterized as a non-radioactive surrogate of a novel Tc-containing fatty acid derivative prepared according to the tricarbon­yl/dithio­ether design with the objective of developing new Tc-based radiopharmaceuticals for the non-invasive diagnosis of myocardial metabolism. The Re chelate contains the metal in the oxidation state +1 and is attached to the terminal position of a fatty acid. The complex formation was accomplished by a ligand exchange reaction using [NBu₄]₂[Re(CO)₃Br₃] as starting material.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.013 Å
• Disorder in main residue
• R factor = 0.061
• wR factor = 0.160
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          2

Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.95
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C1'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Re1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13

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

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

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Bromotricarbonyl{15-[2-(methylsulfanyl)ethylsulfanyl]pentadecanoic acid-κ²S,S'}rhenium(I)

Crystal data

[ReBr(C18H36O2S2)(CO)3]	F(000) = 1376
Mr = 698.73	Dx = 1.771 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 911 reflections
a = 7.486 (5) Å	θ = 3.5–29.6°
b = 12.041 (8) Å	µ = 6.35 mm^−1
c = 29.07 (2) Å	T = 273 K
β = 90.349 (16)°	Block, colorless
V = 2620 (3) Å^3	0.45 × 0.35 × 0.25 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4364 independent reflections
Radiation source: fine-focus sealed tube	3820 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→8
Tmin = 0.076, Tmax = 0.205	k = −14→14
9728 measured reflections	l = −34→34

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.0819P)^2 + 15.1703P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.017
4364 reflections	Δρmax = 2.89 e Å^−3
277 parameters	Δρmin = −1.98 e Å^−3
95 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (4)

Special details

Experimental. ESI-MS (MeOH) (m/z) 697 [M—H]^-. IR (KBr, cm^-1): 2029, 1949, 1899 (ν C≡O); 1712 (ν C ═O).

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	Occ. (<1)
Re1	0.38888 (5)	0.95637 (3)	0.203953 (13)	0.0372 (2)
Br1	0.5600 (2)	1.05851 (18)	0.13951 (7)	0.0634 (7)	0.757 (5)
O1	0.158 (2)	0.8423 (17)	0.2735 (6)	0.073 (5)*	0.757 (5)
C1	0.264 (3)	0.8754 (18)	0.2493 (6)	0.073 (5)*	0.757 (5)
Br1'	0.2037 (8)	0.8550 (6)	0.2627 (2)	0.068 (2)	0.243 (5)
O1'	0.604 (6)	1.091 (4)	0.1351 (14)	0.073 (5)*	0.24
C1'	0.521 (8)	1.042 (5)	0.1614 (19)	0.073 (5)*	0.24
S1	0.1944 (3)	1.1194 (2)	0.21858 (9)	0.0455 (6)
S2	0.1838 (3)	0.9189 (2)	0.13855 (9)	0.0398 (5)
O2	0.5948 (13)	0.7418 (9)	0.1882 (4)	0.084 (3)
O3	0.6646 (12)	1.0268 (8)	0.2770 (4)	0.073 (3)
O4	−1.8066 (10)	0.0397 (7)	0.0243 (3)	0.060 (2)
O5	−1.9155 (9)	0.0926 (8)	−0.0434 (3)	0.063 (2)
H5A	−1.9970	0.0510	−0.0358	0.094*
C2	0.5209 (14)	0.8253 (11)	0.1932 (5)	0.061 (3)
C3	0.5597 (14)	1.0002 (10)	0.2499 (3)	0.045 (2)
C4	0.2754 (17)	1.2422 (9)	0.1921 (5)	0.065 (3)
H4A	0.1962	1.3028	0.1987	0.097*
H4B	0.2815	1.2313	0.1594	0.097*
H4C	0.3925	1.2589	0.2039	0.097*
C5	0.0023 (14)	1.0895 (10)	0.1828 (5)	0.060 (3)
H5B	−0.0729	1.0360	0.1985	0.071*
H5C	−0.0665	1.1571	0.1787	0.071*
C6	0.0515 (15)	1.0438 (8)	0.1359 (5)	0.051 (3)
H6A	0.1174	1.1000	0.1192	0.062*
H6B	−0.0573	1.0285	0.1187	0.062*
C7	0.0180 (12)	0.8136 (7)	0.1519 (4)	0.045 (2)
H7A	−0.0183	0.8207	0.1838	0.054*
H7B	−0.0867	0.8238	0.1326	0.054*
C8	0.0965 (11)	0.6997 (6)	0.1439 (4)	0.047 (2)
H8A	0.1947	0.6879	0.1652	0.057*
H8B	0.1442	0.6963	0.1129	0.057*
C9	−0.0391 (11)	0.6078 (8)	0.1498 (3)	0.047 (2)
H9A	−0.0972	0.6175	0.1793	0.056*
H9B	0.0235	0.5373	0.1506	0.056*
C10	−0.1815 (11)	0.6024 (8)	0.1126 (3)	0.044 (2)
H10A	−0.2379	0.6747	0.1101	0.053*
H10B	−0.1242	0.5868	0.0834	0.053*
C11	−0.3247 (11)	0.5162 (8)	0.1206 (3)	0.047 (2)
H11A	−0.3761	0.5286	0.1507	0.056*
H11B	−0.2692	0.4434	0.1210	0.056*
C12	−0.4739 (11)	0.5155 (8)	0.0853 (3)	0.048 (3)
H12A	−0.4235	0.5018	0.0551	0.058*
H12B	−0.5294	0.5883	0.0846	0.058*
C13	−0.6156 (11)	0.4291 (8)	0.0948 (3)	0.045 (2)
H13A	−0.6695	0.4447	0.1243	0.054*
H13B	−0.5594	0.3567	0.0967	0.054*
C14	−0.7607 (11)	0.4259 (8)	0.0583 (4)	0.048 (3)
H14A	−0.7062	0.4099	0.0289	0.058*
H14B	−0.8150	0.4988	0.0562	0.058*
C15	−0.9063 (10)	0.3410 (8)	0.0669 (3)	0.048 (3)
H15A	−0.8511	0.2684	0.0699	0.058*
H15B	−0.9620	0.3581	0.0961	0.058*
C16	−1.0508 (11)	0.3343 (9)	0.0304 (3)	0.048 (2)
H16A	−0.9958	0.3162	0.0013	0.058*
H16B	−1.1059	0.4068	0.0273	0.058*
C17	−1.1951 (10)	0.2497 (8)	0.0402 (3)	0.042 (2)
H17A	−1.2508	0.2677	0.0693	0.051*
H17B	−1.1404	0.1770	0.0433	0.051*
C18	−1.3380 (10)	0.2443 (9)	0.0032 (3)	0.047 (2)
H18A	−1.2844	0.2184	−0.0252	0.056*
H18B	−1.3836	0.3186	−0.0023	0.056*
C19	−1.4925 (10)	0.1686 (8)	0.0152 (3)	0.043 (2)
H19A	−1.4467	0.0949	0.0217	0.051*
H19B	−1.5493	0.1961	0.0429	0.051*
C20	−1.6301 (11)	0.1611 (10)	−0.0228 (3)	0.054 (3)
H20A	−1.6691	0.2357	−0.0305	0.065*
H20B	−1.5737	0.1300	−0.0498	0.065*
C21	−1.7917 (11)	0.0925 (9)	−0.0116 (4)	0.044 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.0344 (3)	0.0373 (3)	0.0400 (3)	−0.00284 (14)	−0.00122 (16)	−0.00036 (15)
Br1	0.0424 (10)	0.0892 (15)	0.0587 (11)	−0.0179 (7)	0.0073 (7)	0.0106 (9)
Br1'	0.063 (4)	0.081 (5)	0.059 (4)	−0.011 (3)	0.005 (4)	−0.003 (3)
S1	0.0519 (13)	0.0376 (14)	0.0470 (15)	0.0008 (10)	0.0001 (11)	−0.0108 (11)
S2	0.0337 (11)	0.0413 (14)	0.0444 (14)	−0.0047 (9)	0.0017 (10)	−0.0039 (10)
O2	0.079 (6)	0.073 (7)	0.100 (8)	0.024 (5)	−0.008 (5)	−0.021 (6)
O3	0.066 (5)	0.079 (7)	0.074 (7)	−0.006 (4)	−0.024 (5)	−0.011 (5)
O4	0.054 (4)	0.068 (6)	0.058 (5)	−0.021 (4)	−0.004 (4)	0.009 (4)
O5	0.045 (4)	0.081 (6)	0.063 (5)	−0.026 (4)	−0.008 (4)	0.001 (4)
C2	0.039 (5)	0.065 (8)	0.080 (9)	−0.010 (5)	−0.014 (5)	−0.006 (6)
C3	0.059 (6)	0.051 (6)	0.027 (5)	−0.001 (5)	0.002 (5)	−0.006 (4)
C4	0.085 (8)	0.026 (6)	0.084 (9)	−0.009 (5)	−0.015 (7)	−0.004 (5)
C5	0.046 (6)	0.043 (6)	0.090 (9)	0.007 (5)	0.005 (6)	−0.019 (6)
C6	0.046 (6)	0.033 (6)	0.075 (8)	−0.005 (4)	−0.019 (5)	0.003 (5)
C7	0.041 (5)	0.054 (6)	0.041 (6)	−0.013 (4)	−0.003 (4)	−0.013 (5)
C8	0.041 (5)	0.041 (6)	0.060 (7)	−0.004 (4)	−0.004 (5)	−0.011 (5)
C9	0.054 (6)	0.032 (6)	0.055 (7)	−0.008 (4)	−0.004 (5)	−0.011 (4)
C10	0.041 (5)	0.053 (6)	0.039 (6)	−0.016 (4)	−0.001 (4)	−0.001 (4)
C11	0.041 (5)	0.041 (6)	0.058 (7)	−0.006 (4)	0.000 (5)	−0.008 (5)
C12	0.047 (6)	0.039 (6)	0.059 (7)	−0.016 (4)	−0.003 (5)	−0.004 (5)
C13	0.036 (5)	0.045 (6)	0.055 (7)	−0.014 (4)	0.001 (4)	0.002 (5)
C14	0.041 (5)	0.040 (6)	0.064 (7)	−0.008 (4)	−0.012 (5)	0.008 (5)
C15	0.034 (5)	0.048 (6)	0.063 (7)	−0.011 (4)	−0.005 (4)	−0.002 (5)
C16	0.044 (5)	0.051 (6)	0.050 (6)	−0.013 (4)	−0.004 (5)	0.002 (5)
C17	0.030 (4)	0.047 (6)	0.051 (6)	−0.003 (4)	−0.006 (4)	−0.004 (5)
C18	0.038 (5)	0.049 (6)	0.053 (6)	−0.008 (4)	−0.005 (4)	−0.001 (5)
C19	0.036 (5)	0.040 (6)	0.052 (6)	−0.005 (4)	−0.011 (4)	0.000 (4)
C20	0.041 (5)	0.058 (7)	0.063 (7)	−0.016 (5)	−0.003 (5)	0.001 (5)
C21	0.029 (4)	0.055 (7)	0.049 (6)	−0.006 (4)	−0.007 (4)	−0.008 (5)

Geometric parameters (Å, º)

Re1—C2	1.889 (14)	C9—H9B	0.9700
Re1—C1	1.890 (9)	C10—C11	1.512 (7)
Re1—C1'	1.896 (10)	C10—H10A	0.9700
Re1—C3	1.918 (11)	C10—H10B	0.9700
Re1—S2	2.478 (3)	C11—C12	1.512 (7)
Re1—S1	2.482 (3)	C11—H11A	0.9700
Re1—Br1'	2.522 (6)	C11—H11B	0.9700
Re1—Br1	2.587 (2)	C12—C13	1.513 (7)
O1—C1	1.134 (9)	C12—H12A	0.9700
O1'—C1'	1.146 (10)	C12—H12B	0.9700
S1—C4	1.776 (12)	C13—C14	1.514 (7)
S1—C5	1.805 (12)	C13—H13A	0.9700
S2—C6	1.802 (11)	C13—H13B	0.9700
S2—C7	1.818 (10)	C14—C15	1.516 (7)
O2—C2	1.157 (15)	C14—H14A	0.9700
O3—C3	1.154 (13)	C14—H14B	0.9700
O4—C21	1.228 (13)	C15—C16	1.513 (7)
O5—C21	1.306 (12)	C15—H15A	0.9700
O5—H5A	0.8200	C15—H15B	0.9700
C4—H4A	0.9600	C16—C17	1.513 (7)
C4—H4B	0.9600	C16—H16A	0.9700
C4—H4C	0.9600	C16—H16B	0.9700
C5—C6	1.519 (17)	C17—C18	1.514 (7)
C5—H5B	0.9700	C17—H17A	0.9700
C5—H5C	0.9700	C17—H17B	0.9700
C6—H6A	0.9700	C18—C19	1.515 (7)
C6—H6B	0.9700	C18—H18A	0.9700
C7—C8	1.512 (7)	C18—H18B	0.9700
C7—H7A	0.9700	C19—C20	1.509 (7)
C7—H7B	0.9700	C19—H19A	0.9700
C8—C9	1.512 (7)	C19—H19B	0.9700
C8—H8A	0.9700	C20—C21	1.503 (7)
C8—H8B	0.9700	C20—H20A	0.9700
C9—C10	1.515 (7)	C20—H20B	0.9700
C9—H9A	0.9700
C2—Re1—C1	86.9 (8)	C8—C9—H9B	108.6
C2—Re1—C1'	94 (2)	C10—C9—H9B	108.6
C1—Re1—C1'	176 (2)	H9A—C9—H9B	107.5
C2—Re1—C3	89.8 (5)	C11—C10—C9	114.6 (7)
C1—Re1—C3	89.2 (8)	C11—C10—H10A	108.6
C1'—Re1—C3	87 (2)	C9—C10—H10A	108.6
C2—Re1—S2	92.5 (4)	C11—C10—H10B	108.6
C1—Re1—S2	97.8 (7)	C9—C10—H10B	108.6
C1'—Re1—S2	86 (2)	H10A—C10—H10B	107.6
C3—Re1—S2	172.7 (3)	C10—C11—C12	114.9 (8)
C2—Re1—S1	175.5 (3)	C10—C11—H11A	108.5
C1—Re1—S1	89.7 (7)	C12—C11—H11A	108.5
C1'—Re1—S1	89 (2)	C10—C11—H11B	108.5
C3—Re1—S1	93.0 (3)	C12—C11—H11B	108.5
S2—Re1—S1	85.07 (9)	H11A—C11—H11B	107.5
C2—Re1—Br1'	89.9 (4)	C11—C12—C13	113.3 (8)
C1—Re1—Br1'	3.8 (7)	C11—C12—H12A	108.9
C1'—Re1—Br1'	176 (2)	C13—C12—H12A	108.9
C3—Re1—Br1'	91.6 (3)	C11—C12—H12B	108.9
S2—Re1—Br1'	95.25 (17)	C13—C12—H12B	108.9
S1—Re1—Br1'	86.61 (19)	H12A—C12—H12B	107.7
C2—Re1—Br1	90.9 (4)	C12—C13—C14	113.0 (7)
C1—Re1—Br1	177.2 (7)	C12—C13—H13A	109.0
C1'—Re1—Br1	6 (2)	C14—C13—H13A	109.0
C3—Re1—Br1	92.4 (3)	C12—C13—H13B	109.0
S2—Re1—Br1	80.67 (8)	C14—C13—H13B	109.0
S1—Re1—Br1	92.39 (9)	H13A—C13—H13B	107.8
Br1'—Re1—Br1	175.87 (16)	C13—C14—C15	114.5 (7)
O1—C1—Re1	164 (2)	C13—C14—H14A	108.6
O1'—C1'—Re1	178 (6)	C15—C14—H14A	108.6
C4—S1—C5	100.9 (6)	C13—C14—H14B	108.6
C4—S1—Re1	112.5 (4)	C15—C14—H14B	108.6
C5—S1—Re1	102.1 (4)	H14A—C14—H14B	107.6
C6—S2—C7	102.4 (5)	C16—C15—C14	115.6 (8)
C6—S2—Re1	102.6 (4)	C16—C15—H15A	108.4
C7—S2—Re1	112.6 (4)	C14—C15—H15A	108.4
C21—O5—H5A	109.5	C16—C15—H15B	108.4
O2—C2—Re1	176.1 (12)	C14—C15—H15B	108.4
O3—C3—Re1	178.8 (10)	H15A—C15—H15B	107.5
S1—C4—H4A	109.5	C15—C16—C17	114.4 (7)
S1—C4—H4B	109.5	C15—C16—H16A	108.7
H4A—C4—H4B	109.5	C17—C16—H16A	108.7
S1—C4—H4C	109.5	C15—C16—H16B	108.7
H4A—C4—H4C	109.5	C17—C16—H16B	108.7
H4B—C4—H4C	109.5	H16A—C16—H16B	107.6
C6—C5—S1	113.1 (7)	C16—C17—C18	113.4 (7)
C6—C5—H5B	109.0	C16—C17—H17A	108.9
S1—C5—H5B	109.0	C18—C17—H17A	108.9
C6—C5—H5C	109.0	C16—C17—H17B	108.9
S1—C5—H5C	109.0	C18—C17—H17B	108.9
H5B—C5—H5C	107.8	H17A—C17—H17B	107.7
C5—C6—S2	113.6 (9)	C17—C18—C19	113.5 (7)
C5—C6—H6A	108.8	C17—C18—H18A	108.9
S2—C6—H6A	108.8	C19—C18—H18A	108.9
C5—C6—H6B	108.8	C17—C18—H18B	108.9
S2—C6—H6B	108.8	C19—C18—H18B	108.9
H6A—C6—H6B	107.7	H18A—C18—H18B	107.7
C8—C7—S2	109.4 (6)	C20—C19—C18	112.7 (7)
C8—C7—H7A	109.8	C20—C19—H19A	109.1
S2—C7—H7A	109.8	C18—C19—H19A	109.1
C8—C7—H7B	109.8	C20—C19—H19B	109.1
S2—C7—H7B	109.8	C18—C19—H19B	109.1
H7A—C7—H7B	108.2	H19A—C19—H19B	107.8
C7—C8—C9	112.6 (7)	C21—C20—C19	114.9 (8)
C7—C8—H8A	109.1	C21—C20—H20A	108.5
C9—C8—H8A	109.1	C19—C20—H20A	108.5
C7—C8—H8B	109.1	C21—C20—H20B	108.5
C9—C8—H8B	109.1	C19—C20—H20B	108.5
H8A—C8—H8B	107.8	H20A—C20—H20B	107.5
C8—C9—C10	114.8 (8)	O4—C21—O5	122.4 (8)
C8—C9—H9A	108.6	O4—C21—C20	123.1 (9)
C10—C9—H9A	108.6	O5—C21—C20	114.5 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4^i	0.82	1.86	2.681 (11)	174

Symmetry code: (i) −x−4, −y, −z.