The structures of two alkyne-hexacarbonyl-dicobalt complexes are reported, each with potential ATRP initiator substrates as substituents on the alkynes. The complexes each form tetrahedral C2Co2 cluster cores with classical sawhorse conformations, while a feature of the crystal packing is the formation of inversion dimers for both molecules.
Supporting information
CCDC references: 1004257; 1004258
Key indicators
Structure: 1
- Single-crystal X-ray study
- T = 91 K
- Mean
![[sigma]](https://journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.097
- Data-to-parameter ratio = 15.6
Structure: 2
- Single-crystal X-ray study
- T = 91 K
- Mean (C-C) = 0.003 Å
- R factor = 0.031
- wR factor = 0.069
- Data-to-parameter ratio = 27.7
checkCIF/PLATON results
No syntax errors found
Datablock: 1
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. O1 .. 2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A .. O12 .. 2.71 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 6 Why ?
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 8 Why ?
PLAT975_ALERT_2_C Check Calcd Residual Density 0.87A From O12 0.45 eA-3
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Why ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00600 Degree
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Co1 -- C13 .. 7.5 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Co2 -- C22 .. 5.5 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Co2 -- C23 .. 6.0 su
PLAT343_ALERT_2_G Check sp? Angle Range in Main Residue for .. C2
PLAT343_ALERT_2_G Check sp? Angle Range in Main Residue for .. C3
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 87 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
9 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
4 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Datablock: 2
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12C .. BR1 .. 2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A .. BR2 .. 3.01 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A .. O2 .. 2.64 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 62 Why ?
Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00500 Degree
PLAT230_ALERT_2_G Hirshfeld Test Diff for O13 -- C13 .. 5.5 su
PLAT230_ALERT_2_G Hirshfeld Test Diff for O14 -- C14 .. 5.3 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Co1 -- C13 .. 10.9 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Co1 -- C14 .. 9.1 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Co1 -- C15 .. 8.7 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Co2 -- C16 .. 7.8 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Co2 -- C17 .. 6.3 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Co2 -- C18 .. 9.5 su
PLAT343_ALERT_2_G Check sp? Angle Range in Main Residue for .. C1
PLAT343_ALERT_2_G Check sp? Angle Range in Main Residue for .. C2
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 327 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
12 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
10 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
4 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
For both compounds, data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 and SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
(1) [µ
2-
η2,
η2-4-Hydroxybut-2-yn-1-yl
2-bromo-2-methylpropanoate-
κ4C2,
C3:
C2,
C3]bis[tricarbonylcobalt(II)](
Co—
Co)
top
Crystal data top
| [Co2(C8H11BrO3)(CO)6] | Z = 2 |
| Mr = 521.00 | F(000) = 512 |
| Triclinic, P1 | Dx = 1.888 Mg m−3 |
| a = 7.3887 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 11.1147 (12) Å | Cell parameters from 3089 reflections |
| c = 11.7274 (13) Å | θ = 4.7–51.2° |
| α = 78.583 (6)° | µ = 4.03 mm−1 |
| β = 85.239 (6)° | T = 91 K |
| γ = 76.342 (6)° | Irregular fragment, orange-red |
| V = 916.67 (18) Å3 | 0.39 × 0.16 × 0.04 mm |
Data collection top
Bruker APEXII CCD area-detector
diffractometer | 3713 independent reflections |
| Radiation source: fine-focus sealed tube | 2966 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.055 |
| ω scans | θmax = 26.5°, θmin = 3.3° |
Absorption correction: multi-scan
(SADABS; Bruker, 2011) | h = −8→9 |
| Tmin = 0.302, Tmax = 0.855 | k = −13→13 |
| 11686 measured reflections | l = −14→14 |
Refinement top
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
| wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0486P)2]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.001 |
| 3713 reflections | Δρmax = 0.83 e Å−3 |
| 238 parameters | Δρmin = −0.73 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| O1 | −0.0205 (4) | 0.8525 (2) | 1.0602 (2) | 0.0210 (6) | |
| H1 | −0.0387 | 0.7844 | 1.1000 | 0.032* | |
| C1 | −0.1326 (5) | 0.8873 (4) | 0.9601 (3) | 0.0159 (8) | |
| H1A | −0.1616 | 0.9800 | 0.9357 | 0.019* | |
| H1B | −0.2517 | 0.8605 | 0.9803 | 0.019* | |
| C2 | −0.0346 (4) | 0.8277 (3) | 0.8618 (3) | 0.0137 (7) | |
| C3 | 0.0896 (4) | 0.7232 (3) | 0.8429 (3) | 0.0135 (7) | |
| C4 | 0.1996 (5) | 0.6065 (3) | 0.9107 (3) | 0.0131 (7) | |
| H4A | 0.2813 | 0.6282 | 0.9626 | 0.016* | |
| H4B | 0.1144 | 0.5594 | 0.9600 | 0.016* | |
| O2 | 0.3132 (3) | 0.5272 (2) | 0.8345 (2) | 0.0160 (5) | |
| C5 | 0.2596 (5) | 0.4240 (3) | 0.8234 (3) | 0.0147 (8) | |
| O3 | 0.1198 (4) | 0.3939 (2) | 0.8680 (2) | 0.0220 (6) | |
| C6 | 0.3981 (5) | 0.3471 (3) | 0.7453 (3) | 0.0185 (8) | |
| C7 | 0.3045 (6) | 0.2640 (4) | 0.6933 (3) | 0.0254 (9) | |
| H7A | 0.2510 | 0.2089 | 0.7560 | 0.038* | |
| H7B | 0.3967 | 0.2127 | 0.6472 | 0.038* | |
| H7C | 0.2052 | 0.3169 | 0.6431 | 0.038* | |
| C8 | 0.5019 (6) | 0.4259 (4) | 0.6532 (3) | 0.0274 (9) | |
| H8A | 0.5921 | 0.3703 | 0.6097 | 0.041* | |
| H8B | 0.5676 | 0.4733 | 0.6910 | 0.041* | |
| H8C | 0.4126 | 0.4847 | 0.5995 | 0.041* | |
| Br1 | 0.58507 (6) | 0.23943 (4) | 0.85597 (4) | 0.02956 (14) | |
| Co1 | 0.14649 (6) | 0.86999 (5) | 0.73644 (4) | 0.01350 (13) | |
| C11 | 0.3041 (5) | 0.9142 (3) | 0.8218 (3) | 0.0153 (8) | |
| O11 | 0.4032 (3) | 0.9404 (3) | 0.8748 (2) | 0.0216 (6) | |
| C12 | 0.3119 (5) | 0.7980 (4) | 0.6321 (3) | 0.0188 (8) | |
| O12 | 0.4169 (4) | 0.7477 (3) | 0.5703 (2) | 0.0299 (7) | |
| C13 | 0.0360 (5) | 1.0278 (4) | 0.6608 (3) | 0.0235 (9) | |
| O13 | −0.0335 (4) | 1.1244 (3) | 0.6144 (3) | 0.0358 (8) | |
| Co2 | −0.11056 (6) | 0.76340 (5) | 0.73243 (4) | 0.01475 (14) | |
| C21 | −0.2640 (5) | 0.6741 (4) | 0.8176 (3) | 0.0216 (9) | |
| O21 | −0.3575 (4) | 0.6190 (3) | 0.8772 (3) | 0.0327 (7) | |
| C22 | −0.0153 (5) | 0.6651 (4) | 0.6246 (3) | 0.0216 (9) | |
| O22 | 0.0493 (4) | 0.6009 (3) | 0.5607 (3) | 0.0342 (7) | |
| C23 | −0.2750 (5) | 0.8974 (4) | 0.6540 (3) | 0.0216 (8) | |
| O23 | −0.3745 (4) | 0.9823 (3) | 0.6055 (2) | 0.0293 (7) | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O1 | 0.0248 (14) | 0.0207 (15) | 0.0180 (14) | −0.0051 (12) | −0.0019 (11) | −0.0039 (11) |
| C1 | 0.0151 (17) | 0.0157 (19) | 0.0168 (19) | −0.0025 (15) | 0.0022 (14) | −0.0049 (15) |
| C2 | 0.0112 (17) | 0.0148 (19) | 0.0147 (18) | −0.0052 (14) | 0.0024 (13) | −0.0003 (15) |
| C3 | 0.0114 (16) | 0.0169 (19) | 0.0132 (18) | −0.0063 (14) | 0.0017 (13) | −0.0020 (15) |
| C4 | 0.0151 (17) | 0.0108 (18) | 0.0135 (18) | −0.0024 (14) | 0.0019 (14) | −0.0040 (14) |
| O2 | 0.0163 (12) | 0.0133 (13) | 0.0174 (13) | −0.0020 (10) | 0.0043 (10) | −0.0041 (11) |
| C5 | 0.0173 (18) | 0.0119 (18) | 0.0126 (18) | −0.0001 (14) | −0.0014 (14) | −0.0002 (14) |
| O3 | 0.0244 (14) | 0.0199 (15) | 0.0229 (15) | −0.0087 (12) | 0.0082 (11) | −0.0059 (12) |
| C6 | 0.0210 (19) | 0.0128 (19) | 0.0185 (19) | 0.0021 (15) | −0.0010 (15) | −0.0025 (16) |
| C7 | 0.030 (2) | 0.025 (2) | 0.023 (2) | −0.0080 (18) | 0.0048 (17) | −0.0107 (18) |
| C8 | 0.036 (2) | 0.023 (2) | 0.020 (2) | −0.0042 (18) | 0.0098 (18) | −0.0042 (18) |
| Br1 | 0.0302 (2) | 0.0259 (2) | 0.0255 (2) | 0.00937 (17) | −0.00436 (17) | −0.00550 (18) |
| Co1 | 0.0140 (2) | 0.0128 (3) | 0.0133 (3) | −0.00413 (19) | 0.00139 (18) | −0.0009 (2) |
| C11 | 0.0146 (17) | 0.0111 (18) | 0.0171 (19) | 0.0004 (14) | 0.0047 (15) | −0.0014 (15) |
| O11 | 0.0190 (13) | 0.0231 (15) | 0.0241 (15) | −0.0054 (11) | −0.0014 (11) | −0.0065 (12) |
| C12 | 0.023 (2) | 0.019 (2) | 0.0168 (19) | −0.0116 (16) | 0.0023 (16) | −0.0030 (16) |
| O12 | 0.0360 (17) | 0.0303 (17) | 0.0251 (16) | −0.0105 (14) | 0.0129 (13) | −0.0111 (14) |
| C13 | 0.024 (2) | 0.027 (2) | 0.024 (2) | −0.0126 (18) | −0.0019 (17) | −0.0033 (18) |
| O13 | 0.0362 (17) | 0.0196 (17) | 0.046 (2) | −0.0045 (14) | −0.0146 (15) | 0.0100 (15) |
| Co2 | 0.0140 (2) | 0.0139 (3) | 0.0161 (3) | −0.00375 (19) | −0.00161 (19) | −0.0012 (2) |
| C21 | 0.0197 (19) | 0.023 (2) | 0.021 (2) | −0.0035 (17) | −0.0066 (16) | −0.0010 (17) |
| O21 | 0.0254 (15) | 0.0375 (19) | 0.0351 (18) | −0.0164 (14) | −0.0022 (13) | 0.0050 (15) |
| C22 | 0.0204 (19) | 0.020 (2) | 0.025 (2) | −0.0062 (16) | −0.0066 (16) | −0.0017 (18) |
| O22 | 0.0389 (18) | 0.0333 (18) | 0.0346 (18) | −0.0058 (14) | −0.0004 (14) | −0.0193 (15) |
| C23 | 0.0174 (19) | 0.025 (2) | 0.025 (2) | −0.0101 (17) | 0.0015 (16) | −0.0041 (18) |
| O23 | 0.0240 (15) | 0.0204 (16) | 0.0382 (18) | −0.0019 (13) | −0.0105 (13) | 0.0068 (13) |
Geometric parameters (Å, º) top
| O1—C1 | 1.430 (4) | C7—H7A | 0.9800 |
| O1—H1 | 0.8400 | C7—H7B | 0.9800 |
| C1—C2 | 1.493 (5) | C7—H7C | 0.9800 |
| C1—H1A | 0.9900 | C8—H8A | 0.9800 |
| C1—H1B | 0.9900 | C8—H8B | 0.9800 |
| C2—C3 | 1.344 (5) | C8—H8C | 0.9800 |
| Co1—Co2 | 2.4723 (7) | Co1—C11 | 1.805 (4) |
| C2—Co1 | 1.967 (3) | Co1—C12 | 1.819 (4) |
| C2—Co2 | 1.972 (3) | Co1—C13 | 1.833 (4) |
| C3—C4 | 1.476 (5) | C11—O11 | 1.121 (4) |
| C3—Co1 | 1.956 (4) | C12—O12 | 1.141 (5) |
| C3—Co2 | 1.960 (3) | C13—O13 | 1.125 (5) |
| C4—O2 | 1.455 (4) | Co2—C21 | 1.794 (4) |
| C4—H4A | 0.9900 | Co2—C22 | 1.824 (4) |
| C4—H4B | 0.9900 | Co2—C23 | 1.825 (4) |
| O2—C5 | 1.331 (4) | C21—O21 | 1.136 (5) |
| C5—O3 | 1.207 (4) | C22—O22 | 1.135 (5) |
| C5—C6 | 1.535 (5) | C23—O23 | 1.132 (4) |
| C6—C7 | 1.516 (5) | Br1—O1i | 3.307 (3) |
| C6—C8 | 1.526 (5) | O2—O21ii | 2.965 (4) |
| C6—Br1 | 1.981 (3) | | |
| | | |
| C1—O1—H1 | 109.5 | C6—C8—H8A | 109.5 |
| O1—C1—C2 | 111.1 (3) | C6—C8—H8B | 109.5 |
| O1—C1—H1A | 109.4 | H8A—C8—H8B | 109.5 |
| C2—C1—H1A | 109.4 | C6—C8—H8C | 109.5 |
| O1—C1—H1B | 109.4 | H8A—C8—H8C | 109.5 |
| C2—C1—H1B | 109.4 | H8B—C8—H8C | 109.5 |
| H1A—C1—H1B | 108.0 | C6—Br1—O1iii | 68.68 (12) |
| C3—C2—C1 | 140.2 (3) | C11—Co1—C12 | 99.92 (16) |
| C3—C2—Co1 | 69.5 (2) | C11—Co1—C13 | 98.37 (16) |
| C1—C2—Co1 | 135.5 (3) | C12—Co1—C13 | 106.52 (17) |
| C3—C2—Co2 | 69.5 (2) | C11—Co1—C3 | 100.69 (15) |
| C1—C2—Co2 | 135.7 (2) | C12—Co1—C3 | 102.34 (16) |
| Co1—C2—Co2 | 77.75 (13) | C13—Co1—C3 | 141.85 (16) |
| C2—C3—C4 | 138.8 (3) | C11—Co1—C2 | 98.44 (15) |
| C2—C3—Co1 | 70.4 (2) | C12—Co1—C2 | 140.87 (16) |
| C4—C3—Co1 | 135.6 (2) | C13—Co1—C2 | 104.58 (16) |
| C2—C3—Co2 | 70.5 (2) | C3—Co1—C2 | 40.06 (14) |
| C4—C3—Co2 | 135.3 (3) | C11—Co1—Co2 | 148.11 (11) |
| Co1—C3—Co2 | 78.29 (13) | C12—Co1—Co2 | 100.47 (12) |
| O2—C4—C3 | 111.1 (3) | C13—Co1—Co2 | 99.02 (12) |
| O2—C4—H4A | 109.4 | C3—Co1—Co2 | 50.92 (10) |
| C3—C4—H4A | 109.4 | C2—Co1—Co2 | 51.21 (10) |
| O2—C4—H4B | 109.4 | O11—C11—Co1 | 179.3 (3) |
| C3—C4—H4B | 109.4 | O12—C12—Co1 | 176.8 (3) |
| H4A—C4—H4B | 108.0 | O13—C13—Co1 | 179.3 (3) |
| C5—O2—C4 | 117.6 (3) | C21—Co2—C22 | 101.27 (18) |
| C5—O2—O21ii | 142.6 (2) | C21—Co2—C23 | 101.86 (17) |
| C4—O2—O21ii | 89.70 (19) | C22—Co2—C23 | 104.94 (17) |
| O3—C5—O2 | 124.9 (3) | C21—Co2—C3 | 98.31 (15) |
| O3—C5—C6 | 123.7 (3) | C22—Co2—C3 | 103.15 (15) |
| O2—C5—C6 | 111.4 (3) | C23—Co2—C3 | 141.17 (17) |
| C7—C6—C8 | 112.2 (3) | C21—Co2—C2 | 96.59 (16) |
| C7—C6—C5 | 110.8 (3) | C22—Co2—C2 | 141.37 (15) |
| C8—C6—C5 | 114.1 (3) | C23—Co2—C2 | 104.47 (16) |
| C7—C6—Br1 | 109.1 (3) | C3—Co2—C2 | 39.97 (14) |
| C8—C6—Br1 | 107.0 (3) | C21—Co2—Co1 | 145.74 (12) |
| C5—C6—Br1 | 103.0 (2) | C22—Co2—Co1 | 100.40 (12) |
| C6—C7—H7A | 109.5 | C23—Co2—Co1 | 97.76 (12) |
| C6—C7—H7B | 109.5 | C3—Co2—Co1 | 50.79 (10) |
| H7A—C7—H7B | 109.5 | C2—Co2—Co1 | 51.04 (10) |
| C6—C7—H7C | 109.5 | O21—C21—Co2 | 176.0 (3) |
| H7A—C7—H7C | 109.5 | O22—C22—Co2 | 177.1 (3) |
| H7B—C7—H7C | 109.5 | O23—C23—Co2 | 178.5 (3) |
| | | |
| O1—C1—C2—C3 | 30.5 (6) | C3—C4—O2—C5 | −106.2 (3) |
| O1—C1—C2—Co1 | −85.6 (4) | C3—C4—O2—O21ii | 100.4 (3) |
| O1—C1—C2—Co2 | 147.0 (3) | C4—O2—C5—O3 | 3.2 (5) |
| C1—C2—C3—C4 | 0.4 (8) | O21ii—O2—C5—O3 | 135.5 (3) |
| Co1—C2—C3—C4 | 138.1 (5) | C4—O2—C5—C6 | −177.1 (3) |
| Co2—C2—C3—C4 | −137.7 (5) | O21ii—O2—C5—C6 | −44.8 (5) |
| C1—C2—C3—Co1 | −137.7 (5) | O3—C5—C6—C7 | 22.8 (5) |
| Co2—C2—C3—Co1 | 84.12 (10) | O2—C5—C6—C7 | −156.8 (3) |
| C1—C2—C3—Co2 | 138.1 (5) | O3—C5—C6—C8 | 150.7 (4) |
| Co1—C2—C3—Co2 | −84.12 (10) | O2—C5—C6—C8 | −29.0 (4) |
| C2—C3—C4—O2 | 179.8 (4) | O3—C5—C6—Br1 | −93.7 (4) |
| Co1—C3—C4—O2 | −64.1 (4) | O2—C5—C6—Br1 | 86.6 (3) |
| Co2—C3—C4—O2 | 64.1 (4) | | |
| Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y, z; (iii) −x, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O3iii | 0.84 | 2.16 | 2.946 (4) | 156 |
| C4—H4B···O3iii | 0.99 | 2.60 | 3.360 (4) | 134 |
| C7—H7A···O1iii | 0.98 | 2.71 | 3.637 (5) | 157 |
| C1—H1A···O1iv | 0.99 | 2.55 | 3.307 (5) | 133 |
| C8—H8A···O12v | 0.98 | 2.71 | 3.485 (5) | 136 |
| Symmetry codes: (iii) −x, −y+1, −z+2; (iv) −x, −y+2, −z+2; (v) −x+1, −y+1, −z+1. |
(2) [µ
2-
η2,
η2-But-2-yne-1,4-diyl
bis(2-bromo-2-methylpropanoate)-
κ4C2,
C3:
C2,
C3]bis[tricarbonylcobalt(II)](
Co—
Co)
top
Crystal data top
| [Co2(C12H16Br2O4)(CO)6] | Z = 2 |
| Mr = 669.99 | F(000) = 656 |
| Triclinic, P1 | Dx = 1.851 Mg m−3 |
| a = 9.392 (5) Å | Mo Kα radiation, λ = 0.71069 Å |
| b = 10.710 (5) Å | Cell parameters from 5837 reflections |
| c = 13.269 (5) Å | θ = 2.3–30.9° |
| α = 71.314 (5)° | µ = 4.75 mm−1 |
| β = 71.973 (5)° | T = 91 K |
| γ = 84.630 (5)° | Rod, dark red |
| V = 1202.3 (10) Å3 | 0.25 × 0.11 × 0.06 mm |
Data collection top
Bruker APEXII CCD area-detector
diffractometer | 6040 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.037 |
| ω scans | θmax = 32.3°, θmin = 1.7° |
Absorption correction: multi-scan
(SADABS; Bruker, 2011) | h = −14→12 |
| Tmin = 0.611, Tmax = 1.000 | k = −16→16 |
| 21546 measured reflections | l = −19→18 |
| 8127 independent reflections | |
Refinement top
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
| wR(F2) = 0.069 | w = 1/[σ2(Fo2) + (0.0311P)2]
where P = (Fo2 + 2Fc2)/3 |
| S = 0.95 | (Δ/σ)max = 0.008 |
| 8127 reflections | Δρmax = 1.43 e Å−3 |
| 293 parameters | Δρmin = −1.06 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| Br1 | 0.75011 (2) | 0.49577 (2) | 0.81786 (2) | 0.02064 (5) | |
| C7 | 0.6143 (2) | 0.74032 (18) | 0.72699 (17) | 0.0192 (4) | |
| H7A | 0.5332 | 0.7891 | 0.6996 | 0.029* | |
| H7B | 0.7079 | 0.7554 | 0.6657 | 0.029* | |
| H7C | 0.6260 | 0.7708 | 0.7862 | 0.029* | |
| C6 | 0.4399 (2) | 0.56200 (19) | 0.87435 (16) | 0.0167 (4) | |
| H6A | 0.3511 | 0.6010 | 0.8526 | 0.025* | |
| H6B | 0.4533 | 0.5981 | 0.9300 | 0.025* | |
| H6C | 0.4270 | 0.4662 | 0.9061 | 0.025* | |
| C5 | 0.5769 (2) | 0.59405 (18) | 0.77269 (16) | 0.0140 (4) | |
| C4 | 0.5703 (2) | 0.54055 (17) | 0.68077 (16) | 0.0134 (4) | |
| O2 | 0.63231 (16) | 0.58983 (13) | 0.58281 (11) | 0.0182 (3) | |
| O1 | 0.48633 (15) | 0.43066 (12) | 0.72283 (11) | 0.0140 (3) | |
| C3 | 0.4766 (2) | 0.36816 (18) | 0.64290 (15) | 0.0143 (4) | |
| H3A | 0.5769 | 0.3390 | 0.6063 | 0.017* | |
| H3B | 0.4373 | 0.4311 | 0.5848 | 0.017* | |
| C2 | 0.3747 (2) | 0.25397 (17) | 0.70430 (15) | 0.0126 (4) | |
| C1 | 0.3246 (2) | 0.15033 (18) | 0.68869 (15) | 0.0123 (4) | |
| C8 | 0.3382 (2) | 0.09321 (18) | 0.59884 (16) | 0.0147 (4) | |
| H8A | 0.3121 | 0.1598 | 0.5358 | 0.018* | |
| H8B | 0.4424 | 0.0644 | 0.5715 | 0.018* | |
| O3 | 0.23609 (15) | −0.01940 (12) | 0.64364 (11) | 0.0149 (3) | |
| C9 | 0.2214 (2) | −0.07240 (18) | 0.56873 (16) | 0.0142 (4) | |
| O4 | 0.28657 (18) | −0.03238 (14) | 0.47087 (12) | 0.0232 (3) | |
| C10 | 0.1107 (2) | −0.18786 (18) | 0.62156 (17) | 0.0151 (4) | |
| C11 | 0.0394 (3) | −0.2029 (2) | 0.53826 (19) | 0.0235 (5) | |
| H11A | −0.0159 | −0.2866 | 0.5690 | 0.035* | |
| H11B | 0.1175 | −0.2021 | 0.4690 | 0.035* | |
| H11C | −0.0297 | −0.1298 | 0.5228 | 0.035* | |
| C12 | −0.0002 (3) | −0.1871 (2) | 0.7318 (2) | 0.0316 (6) | |
| H12A | −0.0649 | −0.1099 | 0.7201 | 0.047* | |
| H12B | 0.0541 | −0.1835 | 0.7832 | 0.047* | |
| H12C | −0.0615 | −0.2675 | 0.7636 | 0.047* | |
| Br2 | 0.24396 (3) | −0.34166 (2) | 0.65043 (2) | 0.03253 (7) | |
| Co1 | 0.37507 (3) | 0.09639 (2) | 0.82922 (2) | 0.01282 (6) | |
| C13 | 0.2937 (2) | −0.0691 (2) | 0.89243 (17) | 0.0205 (4) | |
| O13 | 0.2402 (2) | −0.17088 (14) | 0.92908 (14) | 0.0318 (4) | |
| C14 | 0.3706 (2) | 0.15581 (19) | 0.94411 (17) | 0.0204 (4) | |
| O14 | 0.3689 (2) | 0.19624 (15) | 1.01387 (13) | 0.0319 (4) | |
| C15 | 0.5735 (3) | 0.06630 (19) | 0.78595 (17) | 0.0192 (4) | |
| O15 | 0.69906 (18) | 0.05518 (17) | 0.75817 (14) | 0.0304 (4) | |
| Co2 | 0.16116 (3) | 0.22826 (2) | 0.78080 (2) | 0.01303 (6) | |
| C16 | 0.0196 (2) | 0.0985 (2) | 0.84785 (17) | 0.0179 (4) | |
| O16 | −0.06494 (18) | 0.01443 (15) | 0.88945 (13) | 0.0269 (4) | |
| C17 | 0.1197 (2) | 0.3291 (2) | 0.87509 (19) | 0.0214 (4) | |
| O17 | 0.0949 (2) | 0.39023 (17) | 0.93381 (15) | 0.0367 (4) | |
| C18 | 0.0866 (2) | 0.3323 (2) | 0.67223 (18) | 0.0203 (4) | |
| O18 | 0.0423 (2) | 0.39556 (16) | 0.60153 (14) | 0.0316 (4) | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Br1 | 0.01709 (11) | 0.02490 (11) | 0.02151 (11) | −0.00005 (8) | −0.00881 (8) | −0.00622 (8) |
| C7 | 0.0267 (12) | 0.0152 (9) | 0.0180 (10) | −0.0055 (8) | −0.0077 (8) | −0.0054 (8) |
| C6 | 0.0178 (10) | 0.0187 (9) | 0.0128 (9) | −0.0030 (8) | −0.0027 (7) | −0.0047 (7) |
| C5 | 0.0169 (10) | 0.0136 (8) | 0.0136 (9) | −0.0020 (7) | −0.0076 (7) | −0.0034 (7) |
| C4 | 0.0150 (10) | 0.0116 (8) | 0.0143 (9) | −0.0023 (7) | −0.0058 (7) | −0.0031 (7) |
| O2 | 0.0226 (8) | 0.0179 (7) | 0.0127 (7) | −0.0087 (6) | −0.0023 (6) | −0.0031 (5) |
| O1 | 0.0181 (7) | 0.0130 (6) | 0.0118 (6) | −0.0078 (5) | −0.0031 (5) | −0.0041 (5) |
| C3 | 0.0191 (10) | 0.0138 (8) | 0.0114 (9) | −0.0060 (7) | −0.0036 (7) | −0.0051 (7) |
| C2 | 0.0122 (9) | 0.0124 (8) | 0.0128 (9) | −0.0011 (7) | −0.0033 (7) | −0.0035 (7) |
| C1 | 0.0105 (9) | 0.0135 (8) | 0.0124 (9) | −0.0008 (7) | −0.0026 (7) | −0.0038 (7) |
| C8 | 0.0146 (10) | 0.0147 (8) | 0.0136 (9) | −0.0066 (7) | −0.0006 (7) | −0.0043 (7) |
| O3 | 0.0168 (7) | 0.0145 (6) | 0.0134 (7) | −0.0068 (5) | −0.0011 (5) | −0.0056 (5) |
| C9 | 0.0129 (9) | 0.0141 (8) | 0.0190 (10) | 0.0017 (7) | −0.0070 (7) | −0.0077 (7) |
| O4 | 0.0279 (9) | 0.0270 (8) | 0.0163 (7) | −0.0110 (7) | −0.0035 (6) | −0.0086 (6) |
| C10 | 0.0140 (10) | 0.0123 (8) | 0.0207 (10) | 0.0002 (7) | −0.0067 (8) | −0.0059 (7) |
| C11 | 0.0216 (12) | 0.0227 (10) | 0.0312 (12) | −0.0052 (9) | −0.0156 (9) | −0.0059 (9) |
| C12 | 0.0267 (13) | 0.0314 (12) | 0.0347 (13) | −0.0165 (10) | 0.0075 (10) | −0.0190 (11) |
| Br2 | 0.03671 (15) | 0.01571 (10) | 0.05628 (17) | 0.00796 (9) | −0.03120 (13) | −0.01135 (10) |
| Co1 | 0.01475 (14) | 0.01102 (12) | 0.01208 (12) | −0.00128 (10) | −0.00391 (10) | −0.00241 (9) |
| C13 | 0.0217 (11) | 0.0184 (10) | 0.0198 (10) | 0.0038 (8) | −0.0049 (8) | −0.0061 (8) |
| O13 | 0.0383 (10) | 0.0140 (7) | 0.0350 (9) | −0.0047 (7) | −0.0020 (8) | −0.0037 (7) |
| C14 | 0.0262 (12) | 0.0153 (9) | 0.0186 (10) | −0.0013 (8) | −0.0096 (9) | −0.0005 (8) |
| O14 | 0.0538 (12) | 0.0281 (8) | 0.0198 (8) | 0.0015 (8) | −0.0169 (8) | −0.0103 (7) |
| C15 | 0.0238 (12) | 0.0183 (9) | 0.0152 (9) | 0.0005 (8) | −0.0089 (8) | −0.0019 (8) |
| O15 | 0.0179 (9) | 0.0433 (10) | 0.0290 (9) | 0.0048 (7) | −0.0082 (7) | −0.0100 (7) |
| Co2 | 0.01267 (13) | 0.01312 (12) | 0.01367 (13) | −0.00069 (10) | −0.00305 (10) | −0.00523 (10) |
| C16 | 0.0151 (10) | 0.0245 (10) | 0.0152 (9) | 0.0001 (8) | −0.0015 (8) | −0.0102 (8) |
| O16 | 0.0219 (9) | 0.0329 (9) | 0.0241 (8) | −0.0118 (7) | 0.0022 (7) | −0.0117 (7) |
| C17 | 0.0194 (11) | 0.0220 (10) | 0.0252 (11) | 0.0015 (8) | −0.0068 (9) | −0.0108 (9) |
| O17 | 0.0380 (11) | 0.0400 (10) | 0.0421 (11) | 0.0063 (8) | −0.0098 (8) | −0.0299 (9) |
| C18 | 0.0180 (11) | 0.0202 (10) | 0.0251 (11) | 0.0012 (8) | −0.0053 (9) | −0.0114 (8) |
| O18 | 0.0359 (10) | 0.0342 (9) | 0.0285 (9) | 0.0105 (7) | −0.0173 (8) | −0.0102 (7) |
Geometric parameters (Å, º) top
| Br1—C5 | 1.998 (2) | O3—C9 | 1.338 (2) |
| C7—C5 | 1.519 (3) | C9—O4 | 1.202 (2) |
| C7—H7A | 0.9800 | C9—C10 | 1.528 (3) |
| C7—H7B | 0.9800 | C10—C11 | 1.513 (3) |
| C7—H7C | 0.9800 | C10—C12 | 1.513 (3) |
| C6—C5 | 1.518 (3) | C10—Br2 | 1.983 (2) |
| C6—H6A | 0.9800 | C11—H11A | 0.9800 |
| C6—H6B | 0.9800 | C11—H11B | 0.9800 |
| C6—H6C | 0.9800 | C11—H11C | 0.9800 |
| C5—C4 | 1.524 (3) | C12—H12A | 0.9800 |
| C4—O2 | 1.207 (2) | C12—H12B | 0.9800 |
| C4—O1 | 1.341 (2) | C12—H12C | 0.9800 |
| O1—C3 | 1.452 (2) | Co1—C15 | 1.803 (2) |
| C3—C2 | 1.474 (3) | Co1—C14 | 1.819 (2) |
| C3—H3A | 0.9900 | Co1—C13 | 1.826 (2) |
| C3—H3B | 0.9900 | C13—O13 | 1.135 (2) |
| C1—C2 | 1.343 (3) | C14—O14 | 1.136 (3) |
| Co1—Co2 | 2.4759 (10) | C15—O15 | 1.128 (3) |
| C1—Co1 | 1.960 (2) | Co2—C18 | 1.805 (2) |
| C1—Co2 | 1.949 (2) | Co2—C16 | 1.820 (2) |
| C2—Co1 | 1.9508 (19) | Co2—C17 | 1.835 (2) |
| C2—Co2 | 1.948 (2) | C16—O16 | 1.136 (2) |
| C1—C8 | 1.473 (3) | C17—O17 | 1.130 (3) |
| C8—O3 | 1.460 (2) | C18—O18 | 1.137 (3) |
| C8—H8A | 0.9900 | O1—Br2i | 3.2960 (18) |
| C8—H8B | 0.9900 | | |
| | | |
| C5—C7—H7A | 109.5 | C11—C10—C9 | 110.93 (16) |
| C5—C7—H7B | 109.5 | C12—C10—C9 | 114.10 (17) |
| H7A—C7—H7B | 109.5 | C11—C10—Br2 | 106.58 (14) |
| C5—C7—H7C | 109.5 | C12—C10—Br2 | 107.91 (15) |
| H7A—C7—H7C | 109.5 | C9—C10—Br2 | 102.33 (13) |
| H7B—C7—H7C | 109.5 | C10—C11—H11A | 109.5 |
| C5—C6—H6A | 109.5 | C10—C11—H11B | 109.5 |
| C5—C6—H6B | 109.5 | H11A—C11—H11B | 109.5 |
| H6A—C6—H6B | 109.5 | C10—C11—H11C | 109.5 |
| C5—C6—H6C | 109.5 | H11A—C11—H11C | 109.5 |
| H6A—C6—H6C | 109.5 | H11B—C11—H11C | 109.5 |
| H6B—C6—H6C | 109.5 | C10—C12—H12A | 109.5 |
| C6—C5—C7 | 112.32 (17) | C10—C12—H12B | 109.5 |
| C6—C5—C4 | 114.29 (16) | H12A—C12—H12B | 109.5 |
| C7—C5—C4 | 111.00 (15) | C10—C12—H12C | 109.5 |
| C6—C5—Br1 | 107.83 (13) | H12A—C12—H12C | 109.5 |
| C7—C5—Br1 | 108.67 (14) | H12B—C12—H12C | 109.5 |
| C4—C5—Br1 | 102.04 (13) | C15—Co1—C14 | 97.61 (10) |
| O2—C4—O1 | 124.07 (18) | C15—Co1—C13 | 103.39 (10) |
| O2—C4—C5 | 124.81 (17) | C14—Co1—C13 | 106.12 (9) |
| O1—C4—C5 | 111.12 (15) | C15—Co1—C2 | 96.50 (8) |
| C4—O1—C3 | 115.91 (14) | C14—Co1—C2 | 105.58 (9) |
| C4—O1—Br2i | 78.24 (11) | C13—Co1—C2 | 139.62 (9) |
| C3—O1—Br2i | 91.57 (10) | C15—Co1—C1 | 102.92 (9) |
| O1—C3—C2 | 107.52 (15) | C14—Co1—C1 | 141.32 (9) |
| O1—C3—H3A | 110.2 | C13—Co1—C1 | 100.56 (9) |
| C2—C3—H3A | 110.2 | C2—Co1—C1 | 40.16 (8) |
| O1—C3—H3B | 110.2 | C15—Co1—Co2 | 146.69 (6) |
| C2—C3—H3B | 110.2 | C14—Co1—Co2 | 96.39 (7) |
| H3A—C3—H3B | 108.5 | C13—Co1—Co2 | 101.48 (8) |
| C1—C2—C3 | 140.49 (18) | C2—Co1—Co2 | 50.52 (6) |
| C1—C2—Co2 | 69.89 (11) | C1—Co1—Co2 | 50.50 (6) |
| C3—C2—Co2 | 135.87 (14) | O13—C13—Co1 | 177.5 (2) |
| C1—C2—Co1 | 70.29 (11) | O14—C14—Co1 | 178.14 (18) |
| C3—C2—Co1 | 133.59 (14) | O15—C15—Co1 | 175.85 (19) |
| Co2—C2—Co1 | 78.85 (7) | C18—Co2—C16 | 100.32 (10) |
| C2—C1—C8 | 139.74 (17) | C18—Co2—C17 | 100.21 (10) |
| C2—C1—Co2 | 69.80 (12) | C16—Co2—C17 | 104.28 (10) |
| C8—C1—Co2 | 134.45 (14) | C18—Co2—C2 | 99.95 (9) |
| C2—C1—Co1 | 69.55 (11) | C16—Co2—C2 | 140.82 (9) |
| C8—C1—Co1 | 136.33 (14) | C17—Co2—C2 | 104.64 (9) |
| Co2—C1—Co1 | 78.60 (8) | C18—Co2—C1 | 98.17 (9) |
| O3—C8—C1 | 108.09 (15) | C16—Co2—C1 | 103.58 (9) |
| O3—C8—H8A | 110.1 | C17—Co2—C1 | 143.05 (9) |
| C1—C8—H8A | 110.1 | C2—Co2—C1 | 40.31 (8) |
| O3—C8—H8B | 110.1 | C18—Co2—Co1 | 147.24 (7) |
| C1—C8—H8B | 110.1 | C16—Co2—Co1 | 97.95 (8) |
| H8A—C8—H8B | 108.4 | C17—Co2—Co1 | 101.33 (7) |
| C9—O3—C8 | 115.40 (14) | C2—Co2—Co1 | 50.63 (6) |
| O4—C9—O3 | 123.67 (18) | C1—Co2—Co1 | 50.90 (6) |
| O4—C9—C10 | 124.03 (18) | O16—C16—Co2 | 177.62 (19) |
| O3—C9—C10 | 112.30 (16) | O17—C17—Co2 | 179.3 (2) |
| C11—C10—C12 | 113.98 (19) | O18—C18—Co2 | 177.7 (2) |
| | | |
| C6—C5—C4—O2 | 151.45 (19) | Co1—C2—C1—C8 | −139.0 (3) |
| C7—C5—C4—O2 | 23.2 (3) | C3—C2—C1—Co2 | −139.2 (3) |
| Br1—C5—C4—O2 | −92.5 (2) | Co1—C2—C1—Co2 | 84.98 (6) |
| C6—C5—C4—O1 | −28.7 (2) | C3—C2—C1—Co1 | 135.8 (3) |
| C7—C5—C4—O1 | −156.98 (16) | Co2—C2—C1—Co1 | −84.98 (6) |
| Br1—C5—C4—O1 | 87.39 (16) | C2—C1—C8—O3 | −174.7 (2) |
| O2—C4—O1—C3 | 2.0 (3) | Co2—C1—C8—O3 | −60.5 (2) |
| C5—C4—O1—C3 | −177.82 (15) | Co1—C1—C8—O3 | 68.3 (2) |
| O2—C4—O1—Br2i | −83.95 (19) | C1—C8—O3—C9 | 172.04 (16) |
| C5—C4—O1—Br2i | 96.19 (14) | C8—O3—C9—O4 | 0.2 (3) |
| C4—O1—C3—C2 | −177.40 (15) | C8—O3—C9—C10 | −178.94 (15) |
| Br2i—O1—C3—C2 | −99.72 (14) | O4—C9—C10—C11 | −26.6 (3) |
| O1—C3—C2—C1 | −173.2 (2) | O3—C9—C10—C11 | 152.47 (17) |
| O1—C3—C2—Co2 | 68.6 (2) | O4—C9—C10—C12 | −157.0 (2) |
| O1—C3—C2—Co1 | −58.2 (2) | O3—C9—C10—C12 | 22.1 (2) |
| C3—C2—C1—C8 | −3.2 (5) | O4—C9—C10—Br2 | 86.7 (2) |
| Co2—C2—C1—C8 | 136.1 (3) | O3—C9—C10—Br2 | −94.18 (16) |
| Symmetry code: (i) x, y+1, z. |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12C···Br1ii | 0.98 | 2.99 | 3.961 (3) | 170 |
| C6—H6A···Br2i | 0.98 | 3.01 | 3.788 (2) | 137 |
| C8—H8B···O4iii | 0.99 | 2.45 | 3.411 (3) | 165 |
| C3—H3B···O2iv | 0.99 | 2.58 | 3.341 (3) | 133 |
| C8—H8A···O2iv | 0.99 | 2.64 | 3.454 (3) | 139 |
| Symmetry codes: (i) x, y+1, z; (ii) x−1, y−1, z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1. |
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