metal-organic compounds
fac-Bromidotricarbonyl[2-(diisopropylphosphanyl)benzaldehyde-κ2O,P]rhenium(I)
aEuropean Commission, Joint Research Centre, Institute for Transuranium Elements, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany, and bIKFT, KIT-Campus Nord, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
*Correspondence e-mail: olaf.walter@ec.europa.eu
The structure of the title complex, [ReBr(C13H19OP)(CO)3], displays a facial coordination of the three CO ligands and a κ2O,P coordination mode of the 2-diisopropylphosphinobenzaldehyde ligands. The Re—C bond distance for the CO ligand trans to the P atom is, due to its trans influence, elongated to 1.943 (3) Å, showing that this CO ligand is more weakly bound to the Re centre than the other two.
Related literature
For the structures of halo-fac-tricarbonyl-[κ2O,P-(ligand)]rhenium(I) complexes with ligands based on 2-diphenylphosphinobenzaldehyde or 2-diphenylphosphinobenzoic acid derivatives, see: Correia et al. (2001); Chen et al. (2001); Palma et al. (2004).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XPMA (Zsolnai, 1996), ORTEP (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812035957/vn2046sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035957/vn2046Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035957/vn2046Isup3.mol
The title compound was obtained from the reaction of 371.0 mg (1.38 mmol) 2-diisopropylphosphinobenzaldehydedimethylacetale and 561.5 mg (1.38 mmol) bromo-pentacarbonyl-rhenium(I) in refluxing thf (30 ml) after recrystallization from diethylether in 93% yield (736 mg). Single crystals of the title compound were grown in an NMR tube with CDCl3 as the solvant.
The position of the H atom located at the aldehyde carbon atom was localized and refined together with its isotropic displacement parameter. The positions of all other H atoms were calculated at geometrical positions according to the
of the atoms they are bound to. The isotropic U values of the hydrogen atoms were refined group-wisely.Data collection: SMART (Bruker, 1997); cell
SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XPMA (Zsolnai, 1996), ORTEP (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Molecular structure of the title compound with displacement ellipsoids at the 50% probability level. |
[ReBr(C13H19OP)(CO)3] | F(000) = 1088 |
Mr = 572.39 | Dx = 2.082 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 165 reflections |
a = 10.750 (2) Å | θ = 2.3–28.3° |
b = 15.194 (3) Å | µ = 8.94 mm−1 |
c = 13.699 (3) Å | T = 200 K |
β = 125.29 (3)° | Cube, orange |
V = 1826.4 (9) Å3 | 0.43 × 0.33 × 0.31 mm |
Z = 4 |
Siemens SMART 1000 CCD diffractometer | 4436 independent reflections |
Radiation source: fine-focus sealed tube | 4095 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 8 pixels mm-1 | θmax = 28.3°, θmin = 2.3° |
ω scans | h = −14→14 |
Absorption correction: numerical SADABS (Bruker, 1997) | k = −19→19 |
Tmin = 0.631, Tmax = 1 | l = −17→17 |
18487 measured reflections |
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)] = 0.018 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0228P)2 + 0.987P] where P = (Fo2 + 2Fc2)/3 |
4436 reflections | (Δ/σ)max = 0.002 |
221 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −1.04 e Å−3 |
[ReBr(C13H19OP)(CO)3] | V = 1826.4 (9) Å3 |
Mr = 572.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.750 (2) Å | µ = 8.94 mm−1 |
b = 15.194 (3) Å | T = 200 K |
c = 13.699 (3) Å | 0.43 × 0.33 × 0.31 mm |
β = 125.29 (3)° |
Siemens SMART 1000 CCD diffractometer | 4436 independent reflections |
Absorption correction: numerical SADABS (Bruker, 1997) | 4095 reflections with I > 2σ(I) |
Tmin = 0.631, Tmax = 1 | Rint = 0.027 |
18487 measured reflections |
R[F2 > 2σ(F2)] = 0.018 | 0 restraints |
wR(F2) = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.51 e Å−3 |
4436 reflections | Δρmin = −1.04 e Å−3 |
221 parameters |
Experimental. Spectroscopic data: 1H{31P} NMR (CDCl3): δ = 9.71, s, 1H, CHO; 7.99, dd, 3JHH = 7.5 Hz, 4JHH = 1.2 Hz, 1H, CH(arom); 7.89, dt, 3JHH = 7.5 Hz, 4JHH = 1.2 Hz, 1H, CH(arom); 7.78, dt, 3JHH = 7.5 Hz, 4JHH = 1.2 Hz, 1H, CH(arom); 7.72, dd, 3JHH = 7.5 Hz, 4JHH = 1.2 Hz, 1H, CH(arom); 2.94, hept, 3JHH = 7.0 Hz, 1H, CH(Me)2; 2.55, hept, 3JHH = 6.9 Hz, 1H, CH(Me)2; 1.38, d, 3JHH = 7.0 Hz, 3H, CH3; 1.31, d, 3JHH = 7.0 Hz, 3H, CH3; 1.03, d, 3JHH = 7.0 Hz, 3H, CH3; 0.97, d, 3JHH = 6.9 Hz, 3H, CH3; 31P{1H} NMR (CDCl3): δ = 19.7, s; 13C{31P}{1H} NMR (CDCl3): δ = 200.6; 196.2; 190.3; 141.0; 136.0; 132.5; 131.6; 27.9; 23.3; 18.9; 18.2; 17.2; 16.2; IR νCO [cm-1]: 2041, 1949, 1905, 1634; UV vis (CHCl3): 414 nm (ε 2142); 261 nm (ε 9780); UV vis (MeCN): 391 nm (ε 1794); 312 nm (sh); 257 nm (ε 7952); 214 nm (ε 27000) |
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. The data of the structure have been deposited at the CCDC with the reference number 894003 (Allen, 2002). |
x | y | z | Uiso*/Ueq | ||
Re1 | 0.096757 (10) | 0.651316 (6) | 0.822326 (9) | 0.01984 (4) | |
Br1 | 0.09257 (4) | 0.70831 (2) | 1.00026 (3) | 0.03331 (7) | |
P1 | −0.17759 (7) | 0.68270 (4) | 0.68063 (6) | 0.01901 (13) | |
O1 | 0.0136 (2) | 0.53062 (12) | 0.85118 (17) | 0.0246 (4) | |
O2 | 0.2119 (2) | 0.83034 (14) | 0.8052 (2) | 0.0381 (5) | |
O3 | 0.4316 (2) | 0.59455 (16) | 1.0029 (2) | 0.0446 (6) | |
O4 | 0.1170 (3) | 0.57547 (15) | 0.6249 (2) | 0.0387 (5) | |
C1 | −0.2889 (3) | 0.63407 (17) | 0.7300 (2) | 0.0217 (5) | |
C2 | −0.4274 (3) | 0.6705 (2) | 0.6956 (3) | 0.0294 (6) | |
H2 | −0.4596 | 0.7228 | 0.6525 | 0.035 (4)* | |
C3 | −0.5192 (3) | 0.6307 (2) | 0.7243 (3) | 0.0343 (7) | |
H3 | −0.6104 | 0.6571 | 0.7013 | 0.035 (4)* | |
C4 | −0.4759 (3) | 0.5528 (2) | 0.7861 (3) | 0.0320 (6) | |
H4 | −0.5383 | 0.5258 | 0.8038 | 0.035 (4)* | |
C5 | −0.3387 (3) | 0.51476 (19) | 0.8221 (2) | 0.0275 (6) | |
H5 | −0.3092 | 0.4618 | 0.8638 | 0.035 (4)* | |
C6 | −0.2436 (3) | 0.55548 (17) | 0.7962 (2) | 0.0220 (5) | |
C7 | −0.1008 (3) | 0.50735 (17) | 0.8444 (2) | 0.0231 (5) | |
C8 | −0.2409 (3) | 0.79816 (17) | 0.6455 (3) | 0.0273 (6) | |
H8 | −0.3526 | 0.7981 | 0.5939 | 0.038 (9)* | |
C9 | −0.1909 (4) | 0.8520 (2) | 0.7555 (3) | 0.0427 (8) | |
H9A | −0.0820 | 0.8576 | 0.8046 | 0.049 (4)* | |
H9B | −0.2227 | 0.8231 | 0.8000 | 0.049 (4)* | |
H9C | −0.2365 | 0.9093 | 0.7316 | 0.049 (4)* | |
C10 | −0.1865 (4) | 0.8395 (2) | 0.5746 (3) | 0.0390 (8) | |
H10A | −0.2189 | 0.8998 | 0.5572 | 0.049 (4)* | |
H10B | −0.2292 | 0.8077 | 0.5011 | 0.049 (4)* | |
H10C | −0.0773 | 0.8368 | 0.6209 | 0.049 (4)* | |
C11 | −0.2622 (3) | 0.6290 (2) | 0.5325 (3) | 0.0288 (6) | |
H11 | −0.2026 | 0.6485 | 0.5029 | 0.030 (9)* | |
C12 | −0.4282 (4) | 0.6553 (2) | 0.4382 (3) | 0.0429 (8) | |
H12A | −0.4655 | 0.6244 | 0.3650 | 0.048 (4)* | |
H12B | −0.4338 | 0.7176 | 0.4242 | 0.048 (4)* | |
H12C | −0.4892 | 0.6404 | 0.4663 | 0.048 (4)* | |
C13 | −0.2484 (4) | 0.5296 (2) | 0.5436 (3) | 0.0357 (7) | |
H13A | −0.3162 | 0.5073 | 0.5620 | 0.048 (4)* | |
H13B | −0.1455 | 0.5138 | 0.6063 | 0.048 (4)* | |
H13C | −0.2749 | 0.5047 | 0.4694 | 0.048 (4)* | |
C14 | 0.1677 (3) | 0.76221 (19) | 0.8091 (2) | 0.0262 (6) | |
C15 | 0.3070 (3) | 0.6152 (2) | 0.9370 (3) | 0.0296 (6) | |
C16 | 0.1055 (3) | 0.60419 (18) | 0.6968 (3) | 0.0256 (6) | |
H7 | −0.101 (3) | 0.4472 (19) | 0.876 (2) | 0.015 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Re1 | 0.01570 (6) | 0.01934 (6) | 0.02291 (6) | −0.00064 (3) | 0.01024 (4) | 0.00179 (4) |
Br1 | 0.04358 (17) | 0.02932 (15) | 0.02861 (14) | −0.00256 (12) | 0.02177 (13) | −0.00259 (12) |
P1 | 0.0162 (3) | 0.0179 (3) | 0.0219 (3) | −0.0005 (2) | 0.0105 (2) | 0.0015 (3) |
O1 | 0.0244 (9) | 0.0195 (9) | 0.0297 (10) | 0.0009 (7) | 0.0155 (8) | 0.0024 (8) |
O2 | 0.0290 (11) | 0.0302 (11) | 0.0431 (13) | −0.0090 (9) | 0.0139 (10) | 0.0058 (10) |
O3 | 0.0185 (10) | 0.0465 (14) | 0.0523 (14) | 0.0029 (9) | 0.0110 (10) | 0.0147 (11) |
O4 | 0.0445 (13) | 0.0394 (13) | 0.0460 (13) | −0.0008 (10) | 0.0342 (11) | −0.0043 (10) |
C1 | 0.0184 (12) | 0.0227 (13) | 0.0240 (13) | −0.0042 (10) | 0.0122 (10) | −0.0025 (10) |
C2 | 0.0242 (14) | 0.0278 (15) | 0.0385 (16) | −0.0006 (11) | 0.0194 (12) | 0.0019 (12) |
C3 | 0.0220 (14) | 0.0438 (18) | 0.0406 (17) | −0.0017 (12) | 0.0201 (13) | −0.0037 (14) |
C4 | 0.0296 (15) | 0.0386 (17) | 0.0346 (15) | −0.0143 (13) | 0.0225 (13) | −0.0074 (13) |
C5 | 0.0296 (14) | 0.0285 (14) | 0.0261 (13) | −0.0083 (11) | 0.0172 (11) | −0.0033 (11) |
C6 | 0.0238 (12) | 0.0200 (13) | 0.0227 (12) | −0.0051 (10) | 0.0136 (10) | −0.0037 (10) |
C7 | 0.0265 (13) | 0.0186 (13) | 0.0242 (13) | −0.0033 (10) | 0.0147 (11) | −0.0013 (10) |
C8 | 0.0219 (13) | 0.0190 (13) | 0.0375 (15) | 0.0028 (10) | 0.0151 (12) | 0.0069 (11) |
C9 | 0.0440 (19) | 0.0245 (16) | 0.054 (2) | 0.0056 (13) | 0.0251 (17) | −0.0042 (14) |
C10 | 0.0322 (16) | 0.0329 (17) | 0.0437 (19) | −0.0016 (12) | 0.0171 (14) | 0.0165 (14) |
C11 | 0.0243 (13) | 0.0342 (15) | 0.0253 (14) | 0.0002 (11) | 0.0127 (11) | −0.0040 (12) |
C12 | 0.0294 (16) | 0.053 (2) | 0.0275 (16) | −0.0033 (14) | 0.0055 (13) | −0.0007 (14) |
C13 | 0.0361 (16) | 0.0339 (17) | 0.0338 (16) | −0.0083 (13) | 0.0184 (13) | −0.0114 (13) |
C14 | 0.0182 (12) | 0.0294 (15) | 0.0268 (14) | 0.0000 (10) | 0.0106 (10) | 0.0037 (11) |
C15 | 0.0241 (14) | 0.0283 (15) | 0.0338 (15) | −0.0038 (11) | 0.0152 (12) | 0.0044 (12) |
C16 | 0.0210 (12) | 0.0241 (14) | 0.0316 (14) | 0.0002 (10) | 0.0151 (11) | 0.0033 (11) |
Re1—C14 | 1.901 (3) | C5—H5 | 0.9300 |
Re1—C15 | 1.943 (3) | C6—C7 | 1.468 (4) |
Re1—C16 | 1.915 (3) | C7—H7 | 1.01 (3) |
Re1—O1 | 2.1739 (18) | C8—C9 | 1.514 (5) |
Re1—P1 | 2.4655 (13) | C8—C10 | 1.528 (4) |
Re1—Br1 | 2.6116 (6) | C8—H8 | 0.9800 |
P1—C1 | 1.835 (3) | C9—H9A | 0.9600 |
P1—C8 | 1.842 (3) | C9—H9B | 0.9600 |
P1—C11 | 1.865 (3) | C9—H9C | 0.9600 |
O1—C7 | 1.231 (3) | C10—H10A | 0.9600 |
O2—C14 | 1.153 (3) | C10—H10B | 0.9600 |
O3—C15 | 1.144 (3) | C10—H10C | 0.9600 |
O4—C16 | 1.148 (3) | C11—C13 | 1.517 (4) |
C1—C2 | 1.392 (4) | C11—C12 | 1.533 (4) |
C1—C6 | 1.406 (4) | C11—H11 | 0.9800 |
C2—C3 | 1.393 (4) | C12—H12A | 0.9600 |
C2—H2 | 0.9300 | C12—H12B | 0.9600 |
C3—C4 | 1.371 (5) | C12—H12C | 0.9600 |
C3—H3 | 0.9300 | C13—H13A | 0.9600 |
C4—C5 | 1.383 (4) | C13—H13B | 0.9600 |
C4—H4 | 0.9300 | C13—H13C | 0.9600 |
C5—C6 | 1.405 (3) | ||
C14—Re1—C16 | 90.87 (12) | O1—C7—H7 | 118.4 (15) |
C14—Re1—C15 | 89.06 (12) | C6—C7—H7 | 112.5 (15) |
C16—Re1—C15 | 89.00 (12) | C9—C8—C10 | 111.4 (3) |
C14—Re1—O1 | 174.15 (10) | C9—C8—P1 | 112.9 (2) |
C16—Re1—O1 | 94.97 (9) | C10—C8—P1 | 109.7 (2) |
C15—Re1—O1 | 91.35 (10) | C9—C8—H8 | 107.5 |
C14—Re1—P1 | 96.71 (8) | C10—C8—H8 | 107.5 |
C16—Re1—P1 | 91.28 (8) | P1—C8—H8 | 107.5 |
C15—Re1—P1 | 174.22 (8) | C8—C9—H9A | 109.5 |
O1—Re1—P1 | 82.87 (5) | C8—C9—H9B | 109.5 |
C14—Re1—Br1 | 91.10 (9) | H9A—C9—H9B | 109.5 |
C16—Re1—Br1 | 177.00 (8) | C8—C9—H9C | 109.5 |
C15—Re1—Br1 | 88.77 (10) | H9A—C9—H9C | 109.5 |
O1—Re1—Br1 | 83.07 (5) | H9B—C9—H9C | 109.5 |
P1—Re1—Br1 | 90.74 (3) | C8—C10—H10A | 109.5 |
C1—P1—C8 | 104.98 (12) | C8—C10—H10B | 109.5 |
C1—P1—C11 | 102.31 (13) | H10A—C10—H10B | 109.5 |
C8—P1—C11 | 104.94 (14) | C8—C10—H10C | 109.5 |
C1—P1—Re1 | 111.71 (9) | H10A—C10—H10C | 109.5 |
C8—P1—Re1 | 118.89 (9) | H10B—C10—H10C | 109.5 |
C11—P1—Re1 | 112.42 (10) | C13—C11—C12 | 110.0 (3) |
C7—O1—Re1 | 136.60 (18) | C13—C11—P1 | 111.6 (2) |
C2—C1—C6 | 117.4 (2) | C12—C11—P1 | 113.6 (2) |
C2—C1—P1 | 120.9 (2) | C13—C11—H11 | 107.1 |
C6—C1—P1 | 121.56 (19) | C12—C11—H11 | 107.1 |
C1—C2—C3 | 121.7 (3) | P1—C11—H11 | 107.1 |
C1—C2—H2 | 119.1 | C11—C12—H12A | 109.5 |
C3—C2—H2 | 119.1 | C11—C12—H12B | 109.5 |
C4—C3—C2 | 120.4 (3) | H12A—C12—H12B | 109.5 |
C4—C3—H3 | 119.8 | C11—C12—H12C | 109.5 |
C2—C3—H3 | 119.8 | H12A—C12—H12C | 109.5 |
C3—C4—C5 | 119.6 (3) | H12B—C12—H12C | 109.5 |
C3—C4—H4 | 120.2 | C11—C13—H13A | 109.5 |
C5—C4—H4 | 120.2 | C11—C13—H13B | 109.5 |
C4—C5—C6 | 120.5 (3) | H13A—C13—H13B | 109.5 |
C4—C5—H5 | 119.7 | C11—C13—H13C | 109.5 |
C6—C5—H5 | 119.7 | H13A—C13—H13C | 109.5 |
C5—C6—C1 | 120.4 (2) | H13B—C13—H13C | 109.5 |
C5—C6—C7 | 113.0 (2) | O2—C14—Re1 | 177.4 (3) |
C1—C6—C7 | 126.6 (2) | O3—C15—Re1 | 178.6 (3) |
O1—C7—C6 | 129.1 (2) | O4—C16—Re1 | 177.2 (2) |
Experimental details
Crystal data | |
Chemical formula | [ReBr(C13H19OP)(CO)3] |
Mr | 572.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 10.750 (2), 15.194 (3), 13.699 (3) |
β (°) | 125.29 (3) |
V (Å3) | 1826.4 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 8.94 |
Crystal size (mm) | 0.43 × 0.33 × 0.31 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD diffractometer |
Absorption correction | Numerical SADABS (Bruker, 1997) |
Tmin, Tmax | 0.631, 1 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18487, 4436, 4095 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.018, 0.045, 1.11 |
No. of reflections | 4436 |
No. of parameters | 221 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.51, −1.04 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XPMA (Zsolnai, 1996), ORTEP (Farrugia, 1997), publCIF (Westrip, 2010).
Re1—C14 | 1.901 (3) | Re1—O1 | 2.1739 (18) |
Re1—C15 | 1.943 (3) | Re1—P1 | 2.4655 (13) |
Re1—C16 | 1.915 (3) | Re1—Br1 | 2.6116 (6) |
Footnotes
‡Current address: European Commission, Joint Research Centre, Institute for Transuranium Elements, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.
Acknowledgements
The authors acknowledge financial support of this work from the Karlsruhe Institute for Technology and the European Commission.
References
Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, X., Femia, F. J., Babich, J. W. & Zubieta, J. (2001). Inorg. Chim. Acta, 315, 147–152. Web of Science CSD CrossRef CAS Google Scholar
Correia, J. D. G., Domingos, A., Santos, I., Alberto, R. & Ortner, K. (2001). Inorg. Chem. 40, 5147–5151. Web of Science CSD CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Palma, E., Correia, J. D. G., Domingos, A., Santos, I., Alberto, R. & Spies, H. (2004). J. Organomet. Chem. 689, 4811–4819. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zsolnai, L. (1996). XPMA. University of Heidelberg, Germany. Google Scholar
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