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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.079
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh - C10 .. 6.38 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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) |