Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040190/bi2048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040190/bi2048Isup2.hkl |
CCDC reference: 627318
Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Rh(C9H6NO)(C18F15P)(CO)] | F(000) = 3136 |
Mr = 807.22 | Dx = 1.957 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 988 reflections |
a = 19.975 (5) Å | θ = 5.4–25.0° |
b = 12.764 (5) Å | µ = 0.82 mm−1 |
c = 22.241 (5) Å | T = 293 K |
β = 104.930 (5)° | Needle, yellow |
V = 5479 (3) Å3 | 0.24 × 0.08 × 0.08 mm |
Z = 8 |
Bruker SMART CCD 1K area-detector diffractometer | 3842 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.064 |
ω scans | θmax = 28°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −26→13 |
Tmin = 0.828, Tmax = 0.938 | k = −16→16 |
18540 measured reflections | l = −26→29 |
6595 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0259P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.079 | (Δ/σ)max = 0.001 |
S = 0.94 | Δρmax = 0.39 e Å−3 |
6595 reflections | Δρmin = −0.44 e Å−3 |
433 parameters |
Experimental. Spectroscopic analysis: 31P{H} NMR (CDCl3, 121.494 MHz, δ, p.p.m.): -7.54 [1J(Rh—P) = 176.7 Hz]; IR (acetone): ν(CO) 1983 cm-1; (KBr): ν(CO) 1985 cm-1. The intensity data was collected on a Siemens SMART CCD 1 K diffractometer using an exposure time of 30 s/frame. A total of 1350 frames were collected with a frame width of 0.3° covering up to θ = 28.00° with 99.6% completeness accomplished. The first 50 frames were recollected at the end of each data collection to check for decay - none was found. |
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. |
x | y | z | Uiso*/Ueq | ||
Rh | 0.807540 (13) | 0.11258 (2) | 0.646222 (12) | 0.03427 (9) | |
P | 0.81007 (4) | −0.03424 (7) | 0.69981 (4) | 0.0346 (2) | |
C1 | 0.83309 (19) | 0.3234 (3) | 0.58667 (15) | 0.0402 (9) | |
H1 | 0.8803 | 0.3127 | 0.6032 | 0.048* | |
C2 | 0.8113 (2) | 0.4133 (3) | 0.55071 (16) | 0.0500 (10) | |
H2 | 0.8437 | 0.4615 | 0.5444 | 0.06* | |
C3 | 0.7430 (2) | 0.4297 (3) | 0.52523 (16) | 0.0495 (10) | |
H3 | 0.7286 | 0.4888 | 0.5008 | 0.059* | |
C4 | 0.69372 (19) | 0.3577 (3) | 0.53553 (15) | 0.0396 (9) | |
C5 | 0.6220 (2) | 0.3642 (3) | 0.51047 (16) | 0.0521 (11) | |
H5 | 0.6034 | 0.4198 | 0.4845 | 0.062* | |
C6 | 0.5792 (2) | 0.2902 (3) | 0.52364 (18) | 0.0564 (11) | |
H6 | 0.5317 | 0.2969 | 0.5071 | 0.068* | |
C7 | 0.60464 (18) | 0.2039 (3) | 0.56151 (17) | 0.0519 (10) | |
H7 | 0.5739 | 0.1544 | 0.5696 | 0.062* | |
C8 | 0.67514 (18) | 0.1915 (3) | 0.58709 (15) | 0.0390 (9) | |
C9 | 0.71968 (17) | 0.2700 (3) | 0.57341 (14) | 0.0357 (8) | |
C10 | 0.90161 (19) | 0.1176 (3) | 0.66680 (17) | 0.0450 (9) | |
C11 | 0.85701 (16) | −0.1527 (3) | 0.68727 (15) | 0.0350 (8) | |
C12 | 0.86697 (18) | −0.2364 (3) | 0.72771 (17) | 0.0427 (9) | |
C13 | 0.8991 (2) | −0.3278 (3) | 0.7178 (2) | 0.0533 (10) | |
C14 | 0.9210 (2) | −0.3372 (3) | 0.6639 (2) | 0.0615 (12) | |
C15 | 0.9120 (2) | −0.2570 (3) | 0.6225 (2) | 0.0583 (11) | |
C16 | 0.87985 (18) | −0.1659 (3) | 0.63405 (17) | 0.0453 (9) | |
C21 | 0.84251 (17) | −0.0020 (3) | 0.78264 (15) | 0.0366 (8) | |
C22 | 0.80329 (19) | 0.0652 (3) | 0.80870 (17) | 0.0422 (9) | |
C23 | 0.8242 (2) | 0.1014 (3) | 0.86846 (18) | 0.0491 (10) | |
C24 | 0.8887 (2) | 0.0744 (3) | 0.90453 (18) | 0.0539 (11) | |
C25 | 0.9302 (2) | 0.0106 (3) | 0.88100 (18) | 0.0510 (10) | |
C26 | 0.90786 (18) | −0.0261 (3) | 0.82011 (17) | 0.0426 (9) | |
C31 | 0.72348 (16) | −0.0915 (2) | 0.68919 (16) | 0.0352 (8) | |
C32 | 0.68571 (18) | −0.1052 (3) | 0.62795 (16) | 0.0420 (9) | |
C33 | 0.6164 (2) | −0.1313 (3) | 0.61126 (18) | 0.0532 (11) | |
C34 | 0.5834 (2) | −0.1487 (3) | 0.6577 (2) | 0.0556 (11) | |
C35 | 0.6189 (2) | −0.1404 (3) | 0.71865 (19) | 0.0504 (10) | |
C36 | 0.68799 (18) | −0.1137 (3) | 0.73373 (16) | 0.0446 (9) | |
N | 0.78941 (14) | 0.2534 (2) | 0.59800 (11) | 0.0331 (6) | |
O4 | 0.70300 (11) | 0.11091 (19) | 0.62182 (11) | 0.0458 (6) | |
O5 | 0.96080 (13) | 0.1214 (2) | 0.67916 (14) | 0.0684 (8) | |
F12 | 0.84386 (11) | −0.23101 (16) | 0.77897 (9) | 0.0567 (6) | |
F13 | 0.90849 (13) | −0.40623 (17) | 0.75872 (12) | 0.0827 (8) | |
F14 | 0.95035 (13) | −0.4272 (2) | 0.65271 (13) | 0.0928 (9) | |
F15 | 0.93183 (14) | −0.2678 (2) | 0.57005 (12) | 0.0914 (9) | |
F16 | 0.87115 (12) | −0.09067 (17) | 0.59064 (10) | 0.0644 (6) | |
F22 | 0.74114 (10) | 0.09651 (16) | 0.77394 (9) | 0.0570 (6) | |
F23 | 0.78237 (13) | 0.16252 (18) | 0.89160 (10) | 0.0719 (7) | |
F24 | 0.91000 (13) | 0.1096 (2) | 0.96285 (10) | 0.0808 (8) | |
F25 | 0.99287 (11) | −0.0156 (2) | 0.91552 (10) | 0.0759 (8) | |
F26 | 0.95240 (10) | −0.08567 (17) | 0.79946 (10) | 0.0581 (6) | |
F32 | 0.71766 (11) | −0.09509 (17) | 0.58205 (9) | 0.0569 (6) | |
F33 | 0.58285 (13) | −0.1412 (2) | 0.55148 (11) | 0.0881 (9) | |
F34 | 0.51608 (12) | −0.1728 (2) | 0.64193 (12) | 0.0915 (9) | |
F35 | 0.58657 (11) | −0.1574 (2) | 0.76344 (11) | 0.0765 (7) | |
F36 | 0.71977 (10) | −0.10715 (17) | 0.79470 (9) | 0.0608 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Rh | 0.02943 (14) | 0.03616 (15) | 0.03665 (15) | 0.00057 (13) | 0.00746 (10) | 0.00593 (14) |
P | 0.0300 (5) | 0.0392 (5) | 0.0338 (5) | −0.0011 (4) | 0.0065 (4) | 0.0055 (4) |
C1 | 0.043 (2) | 0.041 (2) | 0.037 (2) | −0.0040 (17) | 0.0114 (17) | −0.0031 (17) |
C2 | 0.066 (3) | 0.041 (2) | 0.045 (2) | −0.0118 (19) | 0.017 (2) | 0.0063 (18) |
C3 | 0.068 (3) | 0.039 (2) | 0.043 (2) | 0.011 (2) | 0.017 (2) | 0.0058 (18) |
C4 | 0.052 (2) | 0.039 (2) | 0.0290 (19) | 0.0077 (17) | 0.0128 (17) | −0.0019 (16) |
C5 | 0.055 (3) | 0.059 (3) | 0.037 (2) | 0.024 (2) | 0.0040 (19) | 0.0102 (19) |
C6 | 0.039 (2) | 0.074 (3) | 0.054 (3) | 0.020 (2) | 0.008 (2) | 0.003 (2) |
C7 | 0.029 (2) | 0.067 (3) | 0.059 (3) | 0.0044 (18) | 0.0093 (19) | 0.007 (2) |
C8 | 0.038 (2) | 0.043 (2) | 0.038 (2) | 0.0042 (17) | 0.0128 (17) | −0.0005 (17) |
C9 | 0.038 (2) | 0.041 (2) | 0.0276 (19) | 0.0068 (16) | 0.0087 (15) | −0.0011 (15) |
C10 | 0.042 (2) | 0.039 (2) | 0.054 (2) | 0.0042 (19) | 0.0123 (18) | 0.0071 (19) |
C11 | 0.0309 (19) | 0.0361 (19) | 0.038 (2) | −0.0005 (15) | 0.0084 (16) | 0.0043 (16) |
C12 | 0.038 (2) | 0.043 (2) | 0.046 (2) | −0.0066 (17) | 0.0085 (18) | 0.0043 (18) |
C13 | 0.045 (2) | 0.039 (2) | 0.068 (3) | 0.0024 (19) | 0.000 (2) | 0.009 (2) |
C14 | 0.043 (3) | 0.045 (3) | 0.095 (4) | 0.009 (2) | 0.014 (2) | −0.007 (3) |
C15 | 0.054 (3) | 0.059 (3) | 0.066 (3) | 0.008 (2) | 0.022 (2) | −0.007 (2) |
C16 | 0.039 (2) | 0.048 (2) | 0.047 (2) | 0.0009 (18) | 0.0085 (18) | 0.0068 (19) |
C21 | 0.037 (2) | 0.036 (2) | 0.035 (2) | −0.0020 (16) | 0.0075 (16) | 0.0036 (15) |
C22 | 0.043 (2) | 0.042 (2) | 0.041 (2) | −0.0020 (17) | 0.0085 (17) | 0.0034 (18) |
C23 | 0.067 (3) | 0.038 (2) | 0.047 (2) | −0.005 (2) | 0.022 (2) | −0.0026 (19) |
C24 | 0.066 (3) | 0.054 (3) | 0.038 (2) | −0.020 (2) | 0.006 (2) | −0.0028 (19) |
C25 | 0.042 (2) | 0.060 (3) | 0.045 (2) | −0.015 (2) | −0.001 (2) | 0.005 (2) |
C26 | 0.037 (2) | 0.045 (2) | 0.046 (2) | −0.0073 (18) | 0.0116 (18) | −0.0002 (18) |
C31 | 0.0320 (19) | 0.031 (2) | 0.043 (2) | 0.0000 (14) | 0.0098 (16) | 0.0062 (15) |
C32 | 0.043 (2) | 0.039 (2) | 0.046 (2) | −0.0063 (18) | 0.0146 (17) | 0.0032 (18) |
C33 | 0.044 (2) | 0.054 (3) | 0.053 (3) | −0.0123 (19) | −0.003 (2) | −0.009 (2) |
C34 | 0.036 (2) | 0.054 (3) | 0.076 (3) | −0.0151 (18) | 0.012 (2) | −0.001 (2) |
C35 | 0.047 (2) | 0.048 (3) | 0.062 (3) | −0.0063 (18) | 0.024 (2) | 0.0110 (19) |
C36 | 0.039 (2) | 0.045 (2) | 0.049 (2) | −0.0032 (19) | 0.0104 (17) | 0.009 (2) |
N | 0.0379 (17) | 0.0329 (16) | 0.0302 (16) | −0.0008 (13) | 0.0122 (13) | −0.0008 (12) |
O4 | 0.0348 (14) | 0.0463 (15) | 0.0553 (16) | 0.0013 (12) | 0.0097 (11) | 0.0153 (13) |
O5 | 0.0307 (15) | 0.069 (2) | 0.102 (2) | −0.0011 (14) | 0.0118 (15) | 0.0046 (17) |
F12 | 0.0673 (15) | 0.0524 (14) | 0.0516 (14) | −0.0019 (11) | 0.0177 (11) | 0.0143 (11) |
F13 | 0.0859 (19) | 0.0497 (16) | 0.104 (2) | 0.0157 (13) | 0.0094 (15) | 0.0284 (14) |
F14 | 0.085 (2) | 0.0610 (17) | 0.131 (2) | 0.0264 (15) | 0.0263 (17) | −0.0152 (16) |
F15 | 0.107 (2) | 0.095 (2) | 0.090 (2) | 0.0221 (16) | 0.0580 (17) | −0.0127 (16) |
F16 | 0.0853 (18) | 0.0628 (16) | 0.0546 (14) | 0.0115 (12) | 0.0354 (12) | 0.0120 (12) |
F22 | 0.0508 (14) | 0.0638 (15) | 0.0546 (13) | 0.0183 (11) | 0.0104 (10) | −0.0001 (11) |
F23 | 0.0988 (19) | 0.0621 (16) | 0.0617 (15) | 0.0029 (14) | 0.0335 (14) | −0.0157 (13) |
F24 | 0.0979 (19) | 0.0923 (19) | 0.0444 (14) | −0.0285 (15) | 0.0042 (12) | −0.0211 (14) |
F25 | 0.0481 (15) | 0.107 (2) | 0.0584 (15) | −0.0167 (13) | −0.0128 (12) | 0.0019 (14) |
F26 | 0.0318 (12) | 0.0746 (16) | 0.0633 (14) | 0.0033 (10) | 0.0039 (10) | −0.0050 (12) |
F32 | 0.0599 (14) | 0.0685 (16) | 0.0432 (13) | −0.0128 (11) | 0.0145 (10) | −0.0064 (11) |
F33 | 0.0703 (17) | 0.120 (2) | 0.0605 (16) | −0.0356 (15) | −0.0083 (13) | −0.0141 (15) |
F34 | 0.0411 (15) | 0.117 (2) | 0.111 (2) | −0.0323 (14) | 0.0098 (14) | 0.0006 (18) |
F35 | 0.0522 (15) | 0.102 (2) | 0.0846 (18) | −0.0125 (13) | 0.0355 (13) | 0.0204 (15) |
F36 | 0.0540 (14) | 0.0846 (17) | 0.0437 (13) | −0.0169 (12) | 0.0123 (10) | 0.0150 (12) |
N—Rh | 2.077 (3) | C14—F14 | 1.342 (4) |
O4—Rh | 2.018 (2) | C14—C15 | 1.357 (6) |
P—Rh | 2.2145 (11) | C15—F15 | 1.331 (4) |
C1—N | 1.318 (4) | C15—C16 | 1.384 (5) |
C1—C2 | 1.402 (5) | C16—F16 | 1.341 (4) |
C1—H1 | 0.93 | C21—C22 | 1.386 (5) |
C2—C3 | 1.351 (5) | C21—C26 | 1.390 (5) |
C2—H2 | 0.93 | C21—P | 1.835 (3) |
C3—C4 | 1.408 (5) | C22—F22 | 1.343 (4) |
C3—H3 | 0.93 | C22—C23 | 1.367 (5) |
C4—C5 | 1.400 (5) | C23—F23 | 1.339 (4) |
C4—C9 | 1.416 (4) | C23—C24 | 1.374 (5) |
C5—C6 | 1.355 (5) | C24—F24 | 1.335 (4) |
C5—H5 | 0.93 | C24—C25 | 1.359 (5) |
C6—C7 | 1.400 (5) | C25—F25 | 1.332 (4) |
C6—H6 | 0.93 | C25—C26 | 1.393 (5) |
C7—C8 | 1.385 (4) | C26—F26 | 1.339 (4) |
C7—H7 | 0.93 | C31—C32 | 1.388 (4) |
C8—O4 | 1.320 (4) | C31—C36 | 1.388 (5) |
C8—C9 | 1.424 (5) | C31—P | 1.836 (3) |
C9—N | 1.375 (4) | C32—F32 | 1.342 (4) |
C10—O5 | 1.144 (4) | C32—C33 | 1.378 (5) |
C10—Rh | 1.817 (4) | C33—F33 | 1.332 (4) |
C11—C12 | 1.378 (4) | C33—C34 | 1.379 (5) |
C11—C16 | 1.384 (5) | C34—F34 | 1.335 (4) |
C11—P | 1.838 (3) | C34—C35 | 1.364 (5) |
C12—F12 | 1.337 (4) | C35—F35 | 1.338 (4) |
C12—C13 | 1.377 (5) | C35—C36 | 1.376 (5) |
C13—F13 | 1.334 (4) | C36—F36 | 1.344 (4) |
C13—C14 | 1.383 (6) | ||
C10—Rh—O4 | 178.29 (13) | F16—C16—C11 | 121.2 (3) |
C10—Rh—N | 97.53 (13) | F16—C16—C15 | 116.6 (4) |
O4—Rh—N | 80.77 (10) | C11—C16—C15 | 122.2 (4) |
C10—Rh—P | 90.89 (11) | C22—C21—C26 | 115.5 (3) |
O4—Rh—P | 90.82 (7) | C22—C21—P | 117.9 (3) |
N—Rh—P | 170.84 (8) | C26—C21—P | 125.9 (3) |
N—C1—C2 | 122.7 (3) | F22—C22—C23 | 117.7 (3) |
N—C1—H1 | 118.7 | F22—C22—C21 | 118.8 (3) |
C2—C1—H1 | 118.7 | C23—C22—C21 | 123.5 (3) |
C3—C2—C1 | 119.9 (3) | F23—C23—C22 | 120.4 (4) |
C3—C2—H2 | 120.1 | F23—C23—C24 | 120.4 (4) |
C1—C2—H2 | 120.1 | C22—C23—C24 | 119.2 (4) |
C2—C3—C4 | 120.2 (3) | F24—C24—C25 | 120.1 (4) |
C2—C3—H3 | 119.9 | F24—C24—C23 | 120.0 (4) |
C4—C3—H3 | 119.9 | C25—C24—C23 | 119.9 (4) |
C5—C4—C3 | 125.7 (3) | F25—C25—C24 | 120.3 (4) |
C5—C4—C9 | 117.6 (3) | F25—C25—C26 | 119.6 (4) |
C3—C4—C9 | 116.6 (3) | C24—C25—C26 | 120.1 (4) |
C6—C5—C4 | 120.7 (3) | F26—C26—C21 | 121.6 (3) |
C6—C5—H5 | 119.6 | F26—C26—C25 | 116.7 (3) |
C4—C5—H5 | 119.6 | C21—C26—C25 | 121.6 (4) |
C5—C6—C7 | 121.8 (4) | C32—C31—C36 | 115.2 (3) |
C5—C6—H6 | 119.1 | C32—C31—P | 115.6 (2) |
C7—C6—H6 | 119.1 | C36—C31—P | 128.8 (3) |
C8—C7—C6 | 120.6 (4) | F32—C32—C33 | 117.4 (3) |
C8—C7—H7 | 119.7 | F32—C32—C31 | 119.3 (3) |
C6—C7—H7 | 119.7 | C33—C32—C31 | 123.3 (3) |
O4—C8—C7 | 124.0 (3) | F33—C33—C32 | 120.3 (4) |
O4—C8—C9 | 118.8 (3) | F33—C33—C34 | 121.1 (3) |
C7—C8—C9 | 117.2 (3) | C32—C33—C34 | 118.6 (3) |
N—C9—C4 | 122.4 (3) | F34—C34—C35 | 120.7 (4) |
N—C9—C8 | 115.5 (3) | F34—C34—C33 | 119.0 (4) |
C4—C9—C8 | 122.0 (3) | C35—C34—C33 | 120.3 (3) |
O5—C10—Rh | 179.2 (4) | F35—C35—C34 | 120.0 (4) |
C12—C11—C16 | 116.1 (3) | F35—C35—C36 | 120.4 (4) |
C12—C11—P | 122.2 (3) | C34—C35—C36 | 119.7 (4) |
C16—C11—P | 121.6 (3) | F36—C36—C35 | 116.4 (3) |
F12—C12—C13 | 117.3 (3) | F36—C36—C31 | 120.8 (3) |
F12—C12—C11 | 119.5 (3) | C35—C36—C31 | 122.8 (3) |
C13—C12—C11 | 123.2 (4) | C1—N—C9 | 118.2 (3) |
F13—C13—C12 | 121.0 (4) | C1—N—Rh | 130.5 (2) |
F13—C13—C14 | 120.5 (4) | C9—N—Rh | 111.3 (2) |
C12—C13—C14 | 118.5 (4) | C8—O4—Rh | 113.6 (2) |
F14—C14—C15 | 120.5 (4) | C21—P—C31 | 107.20 (16) |
F14—C14—C13 | 119.0 (4) | C21—P—C11 | 105.95 (15) |
C15—C14—C13 | 120.5 (4) | C31—P—C11 | 98.85 (15) |
F15—C15—C14 | 119.9 (4) | C21—P—Rh | 107.67 (11) |
F15—C15—C16 | 120.4 (4) | C31—P—Rh | 112.17 (11) |
C14—C15—C16 | 119.6 (4) | C11—P—Rh | 123.80 (11) |