Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050951/ym2041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050951/ym2041Isup2.hkl |
CCDC reference: 634087
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.025
- wR factor = 0.060
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.15 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXL97.
[RhCl(C22H34OP)2(CO)] | Z = 1 |
Mr = 823.02 | F(000) = 420 |
Triclinic, P1 | Dx = 1.492 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4304 (5) Å | Cell parameters from 6172 reflections |
b = 10.2266 (6) Å | θ = 2.2–28.3° |
c = 11.0438 (10) Å | µ = 0.67 mm−1 |
α = 109.246 (2)° | T = 100 K |
β = 107.972 (2)° | Plate, yellow |
γ = 99.024 (2)° | 0.26 × 0.12 × 0.02 mm |
V = 915.99 (11) Å3 |
Bruker X8 APEXII 4K Kappa CCD diffractometer | 3982 independent reflections |
Radiation source: fine-focus sealed tube | 3695 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 512 pixels mm-1 | θmax = 27.0°, θmin = 2.3° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −13→13 |
Tmin = 0.845, Tmax = 0.986 | l = −14→14 |
11793 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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0215P)2 + 0.66P] where P = (Fo2 + 2Fc2)/3 |
3982 reflections | (Δ/σ)max < 0.001 |
250 parameters | Δρmax = 0.50 e Å−3 |
2 restraints | Δρmin = −0.25 e Å−3 |
Experimental. Spectral data: IR (KBr) ν(CO) = 1974 cm-1, (CH2Cl2) ν(CO) = 1991 cm-1; 1H NMR (CDCl3, 300 MHz): 7.21 (d, 2H), 7.34 (m, 3H), 7.43 (m, 2H), 7.68 (m, 7H), 7.79 (t, 1H); 13C NMR (CDCl3, 75.46 MHz) 125.41 (s), 126.85 (s), 127.76 (s), 128.02 (s), 128.50 (s), 129.77 (s), 130.77 (s), 131.33 (s), 132.25 (s), 132.70 (s), 134.19 (s), 135.09 (s), 136.39 (s), 136.75 (s), 153.21 (s); 31P NMR (CDCl3, 121.49 MHz): 123.7 (d, 1JRh—P = 142 Hz). |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Rh | 0.5000 | 0.5000 | 0.5000 | 0.01141 (6) | |
P | 0.47844 (5) | 0.73195 (5) | 0.55608 (5) | 0.01291 (10) | |
Cl | 0.26051 (19) | 0.42703 (19) | 0.30760 (16) | 0.0131 (4) | 0.50 |
O01 | 0.2082 (5) | 0.4015 (6) | 0.2625 (5) | 0.0137 (11) | 0.50 |
C01 | 0.3174 (7) | 0.4404 (9) | 0.3509 (7) | 0.0109 (13) | 0.50 |
O1 | 0.46784 (15) | 0.79469 (14) | 0.43655 (14) | 0.0171 (3) | |
C11 | 0.5324 (2) | 0.7500 (2) | 0.3374 (2) | 0.0170 (4) | |
C12 | 0.6685 (2) | 0.7139 (2) | 0.3641 (2) | 0.0173 (4) | |
H12 | 0.7223 | 0.7148 | 0.4528 | 0.021* | |
C13 | 0.7298 (2) | 0.67492 (19) | 0.2592 (2) | 0.0169 (4) | |
C14 | 0.8710 (2) | 0.6371 (2) | 0.2823 (2) | 0.0203 (4) | |
H14 | 0.9280 | 0.6390 | 0.3707 | 0.024* | |
C15 | 0.9262 (2) | 0.5979 (2) | 0.1783 (2) | 0.0227 (4) | |
H15 | 1.0209 | 0.5723 | 0.1949 | 0.027* | |
C16 | 0.8435 (2) | 0.5954 (2) | 0.0474 (2) | 0.0243 (4) | |
H16 | 0.8817 | 0.5667 | −0.0245 | 0.029* | |
C17 | 0.7081 (2) | 0.6341 (2) | 0.0227 (2) | 0.0240 (4) | |
H17 | 0.6540 | 0.6333 | −0.0659 | 0.029* | |
C18 | 0.6478 (2) | 0.6750 (2) | 0.1273 (2) | 0.0195 (4) | |
C19 | 0.5075 (2) | 0.7149 (2) | 0.1054 (2) | 0.0229 (4) | |
H19 | 0.4522 | 0.7161 | 0.0180 | 0.027* | |
C110 | 0.4505 (2) | 0.7517 (2) | 0.2078 (2) | 0.0208 (4) | |
H110 | 0.3564 | 0.7781 | 0.1916 | 0.025* | |
C21 | 0.6290 (2) | 0.87653 (19) | 0.7107 (2) | 0.0159 (4) | |
C22 | 0.6263 (2) | 0.8947 (2) | 0.8409 (2) | 0.0258 (4) | |
H22 | 0.5439 | 0.8340 | 0.8470 | 0.031* | |
C23 | 0.7428 (3) | 1.0005 (3) | 0.9612 (2) | 0.0347 (5) | |
H23 | 0.7398 | 1.0125 | 1.0493 | 0.042* | |
C24 | 0.8637 (2) | 1.0888 (2) | 0.9528 (2) | 0.0308 (5) | |
H24 | 0.9439 | 1.1611 | 1.0352 | 0.037* | |
C25 | 0.8676 (2) | 1.0719 (2) | 0.8250 (2) | 0.0268 (5) | |
H25 | 0.9508 | 1.1322 | 0.8195 | 0.032* | |
C26 | 0.7495 (2) | 0.9663 (2) | 0.7033 (2) | 0.0205 (4) | |
H26 | 0.7519 | 0.9562 | 0.6153 | 0.025* | |
C31 | 0.3054 (2) | 0.7584 (2) | 0.58727 (18) | 0.0144 (4) | |
C32 | 0.2235 (2) | 0.6585 (2) | 0.6192 (2) | 0.0187 (4) | |
H32 | 0.2507 | 0.5717 | 0.6135 | 0.022* | |
C33 | 0.1012 (2) | 0.6855 (2) | 0.6596 (2) | 0.0217 (4) | |
H33 | 0.0457 | 0.6176 | 0.6825 | 0.026* | |
C34 | 0.0609 (2) | 0.8109 (2) | 0.6664 (2) | 0.0211 (4) | |
H34 | −0.0223 | 0.8293 | 0.6943 | 0.025* | |
C35 | 0.1412 (2) | 0.9104 (2) | 0.6327 (2) | 0.0216 (4) | |
H35 | 0.1118 | 0.9958 | 0.6359 | 0.026* | |
C36 | 0.2644 (2) | 0.8850 (2) | 0.5943 (2) | 0.0192 (4) | |
H36 | 0.3207 | 0.9537 | 0.5729 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Rh | 0.01270 (10) | 0.01119 (10) | 0.01178 (11) | 0.00487 (7) | 0.00564 (8) | 0.00485 (8) |
P | 0.0155 (2) | 0.0121 (2) | 0.0139 (2) | 0.00541 (18) | 0.00762 (18) | 0.00603 (19) |
Cl | 0.0085 (14) | 0.0151 (10) | 0.0082 (14) | 0.0022 (12) | −0.0019 (9) | 0.0010 (11) |
O01 | 0.013 (3) | 0.016 (3) | 0.010 (3) | 0.005 (2) | 0.003 (2) | 0.004 (2) |
C01 | 0.012 (4) | 0.006 (2) | 0.014 (4) | 0.001 (3) | 0.009 (3) | 0.000 (3) |
O1 | 0.0236 (7) | 0.0184 (7) | 0.0186 (7) | 0.0120 (6) | 0.0136 (6) | 0.0107 (6) |
C11 | 0.0232 (9) | 0.0126 (9) | 0.0185 (9) | 0.0053 (7) | 0.0123 (8) | 0.0064 (7) |
C12 | 0.0215 (9) | 0.0166 (9) | 0.0159 (9) | 0.0059 (8) | 0.0084 (8) | 0.0079 (8) |
C13 | 0.0212 (9) | 0.0115 (9) | 0.0184 (9) | 0.0031 (7) | 0.0097 (8) | 0.0054 (7) |
C14 | 0.0231 (10) | 0.0193 (10) | 0.0207 (10) | 0.0066 (8) | 0.0105 (8) | 0.0087 (8) |
C15 | 0.0238 (10) | 0.0229 (10) | 0.0282 (11) | 0.0107 (8) | 0.0152 (9) | 0.0117 (9) |
C16 | 0.0312 (11) | 0.0234 (11) | 0.0249 (11) | 0.0093 (9) | 0.0189 (9) | 0.0092 (9) |
C17 | 0.0304 (11) | 0.0251 (11) | 0.0200 (10) | 0.0085 (9) | 0.0124 (9) | 0.0106 (9) |
C18 | 0.0236 (9) | 0.0151 (9) | 0.0185 (10) | 0.0037 (8) | 0.0080 (8) | 0.0063 (8) |
C19 | 0.0296 (11) | 0.0245 (11) | 0.0166 (10) | 0.0090 (9) | 0.0096 (8) | 0.0095 (8) |
C110 | 0.0225 (10) | 0.0211 (10) | 0.0230 (10) | 0.0095 (8) | 0.0102 (8) | 0.0111 (8) |
C21 | 0.0166 (8) | 0.0116 (9) | 0.0184 (9) | 0.0065 (7) | 0.0048 (7) | 0.0053 (7) |
C22 | 0.0290 (11) | 0.0254 (11) | 0.0193 (10) | 0.0035 (9) | 0.0061 (9) | 0.0096 (9) |
C23 | 0.0390 (13) | 0.0353 (13) | 0.0187 (11) | 0.0067 (11) | 0.0018 (10) | 0.0080 (10) |
C24 | 0.0228 (10) | 0.0228 (11) | 0.0294 (12) | 0.0067 (9) | −0.0028 (9) | 0.0019 (9) |
C25 | 0.0169 (9) | 0.0180 (10) | 0.0402 (13) | 0.0064 (8) | 0.0083 (9) | 0.0074 (9) |
C26 | 0.0202 (9) | 0.0157 (9) | 0.0271 (11) | 0.0080 (8) | 0.0118 (8) | 0.0065 (8) |
C31 | 0.0144 (8) | 0.0155 (9) | 0.0119 (8) | 0.0050 (7) | 0.0049 (7) | 0.0035 (7) |
C32 | 0.0210 (9) | 0.0159 (9) | 0.0233 (10) | 0.0087 (8) | 0.0111 (8) | 0.0091 (8) |
C33 | 0.0231 (10) | 0.0240 (10) | 0.0243 (10) | 0.0082 (8) | 0.0140 (8) | 0.0119 (9) |
C34 | 0.0175 (9) | 0.0270 (11) | 0.0190 (10) | 0.0109 (8) | 0.0086 (8) | 0.0062 (8) |
C35 | 0.0227 (10) | 0.0170 (10) | 0.0241 (10) | 0.0109 (8) | 0.0079 (8) | 0.0058 (8) |
C36 | 0.0207 (9) | 0.0152 (9) | 0.0222 (10) | 0.0063 (8) | 0.0087 (8) | 0.0072 (8) |
Rh—C01i | 1.818 (6) | C19—C110 | 1.366 (3) |
Rh—C01 | 1.818 (6) | C19—H19 | 0.9500 |
Rh—Pi | 2.3048 (5) | C110—H110 | 0.9500 |
Rh—P | 2.3048 (5) | C21—C26 | 1.386 (3) |
Rh—Cli | 2.3743 (16) | C21—C22 | 1.397 (3) |
Rh—Cl | 2.3743 (16) | C22—C23 | 1.386 (3) |
P—O1 | 1.6314 (13) | C22—H22 | 0.9500 |
P—C31 | 1.8102 (18) | C23—C24 | 1.386 (3) |
P—C21 | 1.8165 (19) | C23—H23 | 0.9500 |
O01—C01 | 1.080 (6) | C24—C25 | 1.377 (3) |
O1—C11 | 1.395 (2) | C24—H24 | 0.9500 |
C11—C12 | 1.364 (3) | C25—C26 | 1.398 (3) |
C11—C110 | 1.408 (3) | C25—H25 | 0.9500 |
C12—C13 | 1.420 (3) | C26—H26 | 0.9500 |
C12—H12 | 0.9500 | C31—C32 | 1.386 (3) |
C13—C14 | 1.416 (3) | C31—C36 | 1.393 (3) |
C13—C18 | 1.422 (3) | C32—C33 | 1.393 (3) |
C14—C15 | 1.373 (3) | C32—H32 | 0.9500 |
C14—H14 | 0.9500 | C33—C34 | 1.380 (3) |
C15—C16 | 1.404 (3) | C33—H33 | 0.9500 |
C15—H15 | 0.9500 | C34—C35 | 1.390 (3) |
C16—C17 | 1.370 (3) | C34—H34 | 0.9500 |
C16—H16 | 0.9500 | C35—C36 | 1.387 (3) |
C17—C18 | 1.412 (3) | C35—H35 | 0.9500 |
C17—H17 | 0.9500 | C36—H36 | 0.9500 |
C18—C19 | 1.419 (3) | ||
C01i—Rh—C01 | 180.000 (1) | C17—C18—C13 | 118.94 (18) |
C01i—Rh—Pi | 88.0 (3) | C19—C18—C13 | 118.68 (18) |
C01—Rh—Pi | 92.0 (3) | C110—C19—C18 | 121.15 (19) |
C01i—Rh—P | 92.0 (3) | C110—C19—H19 | 119.4 |
C01—Rh—P | 88.0 (3) | C18—C19—H19 | 119.4 |
Pi—Rh—P | 180.0 | C19—C110—C11 | 119.50 (19) |
C01i—Rh—Cli | 1.2 (3) | C19—C110—H110 | 120.3 |
C01—Rh—Cli | 178.8 (3) | C11—C110—H110 | 120.3 |
Pi—Rh—Cli | 86.84 (5) | C26—C21—C22 | 119.09 (18) |
P—Rh—Cli | 93.16 (5) | C26—C21—P | 121.73 (15) |
C01i—Rh—Cl | 178.8 (3) | C22—C21—P | 119.15 (14) |
C01—Rh—Cl | 1.2 (3) | C23—C22—C21 | 120.5 (2) |
Pi—Rh—Cl | 93.16 (5) | C23—C22—H22 | 119.7 |
P—Rh—Cl | 86.84 (5) | C21—C22—H22 | 119.7 |
Cli—Rh—Cl | 180.0 | C22—C23—C24 | 120.0 (2) |
O1—P—C31 | 100.91 (8) | C22—C23—H23 | 120.0 |
O1—P—C21 | 102.75 (8) | C24—C23—H23 | 120.0 |
C31—P—C21 | 100.91 (8) | C25—C24—C23 | 120.0 (2) |
O1—P—Rh | 115.52 (5) | C25—C24—H24 | 120.0 |
C31—P—Rh | 115.73 (6) | C23—C24—H24 | 120.0 |
C21—P—Rh | 118.43 (6) | C24—C25—C26 | 120.3 (2) |
O01—C01—Rh | 178.1 (10) | C24—C25—H25 | 119.9 |
C11—O1—P | 123.93 (12) | C26—C25—H25 | 119.9 |
C12—C11—O1 | 123.25 (17) | C21—C26—C25 | 120.1 (2) |
C12—C11—C110 | 121.62 (17) | C21—C26—H26 | 119.9 |
O1—C11—C110 | 115.06 (17) | C25—C26—H26 | 119.9 |
C11—C12—C13 | 119.86 (18) | C32—C31—C36 | 119.95 (17) |
C11—C12—H12 | 120.1 | C32—C31—P | 119.13 (14) |
C13—C12—H12 | 120.1 | C36—C31—P | 120.55 (14) |
C14—C13—C12 | 121.87 (18) | C31—C32—C33 | 120.02 (18) |
C14—C13—C18 | 118.95 (17) | C31—C32—H32 | 120.0 |
C12—C13—C18 | 119.18 (18) | C33—C32—H32 | 120.0 |
C15—C14—C13 | 120.58 (19) | C34—C33—C32 | 119.86 (18) |
C15—C14—H14 | 119.7 | C34—C33—H33 | 120.1 |
C13—C14—H14 | 119.7 | C32—C33—H33 | 120.1 |
C14—C15—C16 | 120.31 (19) | C33—C34—C35 | 120.37 (18) |
C14—C15—H15 | 119.8 | C33—C34—H34 | 119.8 |
C16—C15—H15 | 119.8 | C35—C34—H34 | 119.8 |
C17—C16—C15 | 120.46 (18) | C36—C35—C34 | 119.92 (18) |
C17—C16—H16 | 119.8 | C36—C35—H35 | 120.0 |
C15—C16—H16 | 119.8 | C34—C35—H35 | 120.0 |
C16—C17—C18 | 120.74 (19) | C35—C36—C31 | 119.87 (18) |
C16—C17—H17 | 119.6 | C35—C36—H36 | 120.1 |
C18—C17—H17 | 119.6 | C31—C36—H36 | 120.1 |
C17—C18—C19 | 122.37 (19) | ||
C01i—Rh—P—O1 | 121.7 (3) | C13—C18—C19—C110 | −0.5 (3) |
C01—Rh—P—O1 | −58.3 (3) | C18—C19—C110—C11 | 0.0 (3) |
Cli—Rh—P—O1 | 121.33 (7) | C12—C11—C110—C19 | 0.7 (3) |
Cl—Rh—P—O1 | −58.67 (7) | O1—C11—C110—C19 | 177.61 (17) |
C01i—Rh—P—C31 | −120.8 (3) | O1—P—C21—C26 | −30.05 (17) |
C01—Rh—P—C31 | 59.2 (3) | C31—P—C21—C26 | −134.00 (16) |
Cli—Rh—P—C31 | −121.11 (8) | Rh—P—C21—C26 | 98.61 (16) |
Cl—Rh—P—C31 | 58.89 (8) | O1—P—C21—C22 | 152.10 (16) |
C01i—Rh—P—C21 | −0.8 (3) | C31—P—C21—C22 | 48.15 (18) |
C01—Rh—P—C21 | 179.2 (3) | Rh—P—C21—C22 | −79.23 (17) |
Cli—Rh—P—C21 | −1.12 (8) | C26—C21—C22—C23 | −0.3 (3) |
Cl—Rh—P—C21 | 178.88 (8) | P—C21—C22—C23 | 177.56 (18) |
C31—P—O1—C11 | −153.13 (14) | C21—C22—C23—C24 | −0.3 (4) |
C21—P—O1—C11 | 102.91 (15) | C22—C23—C24—C25 | 0.3 (4) |
Rh—P—O1—C11 | −27.55 (15) | C23—C24—C25—C26 | 0.3 (3) |
P—O1—C11—C12 | −35.1 (2) | C22—C21—C26—C25 | 1.0 (3) |
P—O1—C11—C110 | 147.97 (14) | P—C21—C26—C25 | −176.85 (15) |
O1—C11—C12—C13 | −177.53 (16) | C24—C25—C26—C21 | −1.0 (3) |
C110—C11—C12—C13 | −0.8 (3) | O1—P—C31—C32 | 145.36 (15) |
C11—C12—C13—C14 | 179.76 (17) | C21—P—C31—C32 | −109.22 (16) |
C11—C12—C13—C18 | 0.3 (3) | Rh—P—C31—C32 | 19.92 (17) |
C12—C13—C14—C15 | 179.07 (18) | O1—P—C31—C36 | −41.64 (17) |
C18—C13—C14—C15 | −1.5 (3) | C21—P—C31—C36 | 63.78 (17) |
C13—C14—C15—C16 | 0.3 (3) | Rh—P—C31—C36 | −167.08 (13) |
C14—C15—C16—C17 | 1.0 (3) | C36—C31—C32—C33 | −0.6 (3) |
C15—C16—C17—C18 | −1.0 (3) | P—C31—C32—C33 | 172.40 (15) |
C16—C17—C18—C19 | −179.64 (19) | C31—C32—C33—C34 | 0.7 (3) |
C16—C17—C18—C13 | −0.3 (3) | C32—C33—C34—C35 | 0.2 (3) |
C14—C13—C18—C17 | 1.5 (3) | C33—C34—C35—C36 | −1.1 (3) |
C12—C13—C18—C17 | −179.08 (17) | C34—C35—C36—C31 | 1.2 (3) |
C14—C13—C18—C19 | −179.13 (18) | C32—C31—C36—C35 | −0.3 (3) |
C12—C13—C18—C19 | 0.3 (3) | P—C31—C36—C35 | −173.23 (15) |
C17—C18—C19—C110 | 178.87 (19) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
R | Rh—Cl | Rh—CO | Rh—P | Disorder | Ref. |
2,4,6-Me3C6H2 | 2.341 (1) | 1.834 (4) | 2.320 (1) | no | a |
(CH2)2(CF2)5CF3 | 2.356 (1) | 1.829 (5) | 2.304 (1) | no | b |
2-Naphthyl | 2.374 (2) | 1.818 (6) | 2.305 (1) | yes | c |
Notes: (a) Chahen et al. (2005); (b) Haar et al. (1998); (c) this work. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register