Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012955/bi2004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012955/bi2004Isup2.hkl |
CCDC reference: 608366
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.036
- wR factor = 0.083
- Data-to-parameter ratio = 20.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh - C10 .. 5.75 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus and XPREP (Bruker, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Rh(C9H6NO)(C18H21P)(CO)] | F(000) = 1112 |
Mr = 543.39 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 945 reflections |
a = 10.559 (2) Å | θ = 5.4–25.0° |
b = 13.296 (3) Å | µ = 0.78 mm−1 |
c = 17.658 (4) Å | T = 293 K |
β = 90.99 (3)° | Cuboid, yellow |
V = 2478.7 (9) Å3 | 0.20 × 0.18 × 0.14 mm |
Z = 4 |
Bruker SMART 1K CCD diffractometer | 4036 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
ω scans | θmax = 28°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −13→13 |
Tmin = 0.860, Tmax = 0.899 | k = −16→17 |
16521 measured reflections | l = −14→23 |
5979 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0365P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.083 | (Δ/σ)max = 0.001 |
S = 1.00 | Δρmax = 0.46 e Å−3 |
5979 reflections | Δρmin = −0.36 e Å−3 |
299 parameters |
Experimental. The intensity data were collected on a Siemens SMART 1 K CCD diffractometer using an exposure time of 20 s/frame. A total of 1350 frames were collected with a frame width of 0.3° covering up to θ = 28.00° with 99.9% 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 | 0.047748 (19) | 0.272104 (17) | 0.324590 (13) | 0.03845 (8) | |
P | 0.19854 (6) | 0.15306 (5) | 0.30369 (4) | 0.03637 (17) | |
N | −0.07782 (19) | 0.39729 (17) | 0.32491 (14) | 0.0446 (6) | |
O1 | −0.01287 (19) | 0.27272 (15) | 0.21306 (11) | 0.0507 (5) | |
O2 | 0.1215 (3) | 0.27026 (19) | 0.48725 (14) | 0.0805 (8) | |
C1 | −0.1074 (3) | 0.4589 (2) | 0.3819 (2) | 0.0549 (8) | |
H1 | −0.0807 | 0.4428 | 0.4308 | 0.066* | |
C2 | −0.1781 (3) | 0.5476 (3) | 0.3697 (3) | 0.0701 (11) | |
H2 | −0.1958 | 0.5899 | 0.4101 | 0.084* | |
C3 | −0.2204 (3) | 0.5708 (3) | 0.2984 (3) | 0.0691 (11) | |
H3 | −0.2662 | 0.6298 | 0.2903 | 0.083* | |
C4 | −0.1957 (3) | 0.5067 (2) | 0.2368 (2) | 0.0560 (9) | |
C5 | −0.2383 (3) | 0.5222 (3) | 0.1617 (3) | 0.0728 (11) | |
H5 | −0.2858 | 0.579 | 0.1494 | 0.087* | |
C6 | −0.2099 (3) | 0.4536 (3) | 0.1067 (2) | 0.0753 (11) | |
H6 | −0.2399 | 0.4643 | 0.0575 | 0.09* | |
C7 | −0.1359 (3) | 0.3666 (3) | 0.1224 (2) | 0.0619 (9) | |
H7 | −0.1195 | 0.3209 | 0.084 | 0.074* | |
C8 | −0.0879 (3) | 0.3496 (2) | 0.19523 (18) | 0.0461 (7) | |
C9 | −0.1216 (2) | 0.4196 (2) | 0.25307 (18) | 0.0441 (7) | |
C10 | 0.0931 (3) | 0.2711 (2) | 0.42348 (18) | 0.0501 (7) | |
C11 | 0.1920 (2) | 0.1110 (2) | 0.20408 (15) | 0.0373 (6) | |
H11 | 0.1856 | 0.1721 | 0.1731 | 0.045* | |
C12 | 0.0678 (3) | 0.0515 (2) | 0.18968 (18) | 0.0510 (8) | |
H12A | 0.0717 | −0.0119 | 0.2169 | 0.061* | |
H12B | −0.0033 | 0.0897 | 0.2085 | 0.061* | |
C13 | 0.0482 (3) | 0.0312 (3) | 0.10516 (19) | 0.0618 (9) | |
H13A | −0.0281 | −0.0085 | 0.0974 | 0.074* | |
H13B | 0.0369 | 0.0945 | 0.0786 | 0.074* | |
C14 | 0.1608 (3) | −0.0248 (3) | 0.07274 (19) | 0.0652 (10) | |
H14A | 0.1486 | −0.0325 | 0.0185 | 0.078* | |
H14B | 0.166 | −0.0914 | 0.095 | 0.078* | |
C15 | 0.2841 (3) | 0.0316 (3) | 0.08866 (17) | 0.0570 (8) | |
H15A | 0.2824 | 0.0953 | 0.0619 | 0.068* | |
H15B | 0.3545 | −0.0074 | 0.0698 | 0.068* | |
C16 | 0.3044 (3) | 0.0509 (2) | 0.17354 (17) | 0.0476 (7) | |
H16A | 0.3823 | 0.0882 | 0.1819 | 0.057* | |
H16B | 0.3116 | −0.0127 | 0.2002 | 0.057* | |
C21 | 0.1936 (2) | 0.0360 (2) | 0.35886 (15) | 0.0391 (6) | |
C22 | 0.2971 (3) | −0.0305 (2) | 0.36455 (17) | 0.0469 (7) | |
H22 | 0.3732 | −0.0138 | 0.342 | 0.056* | |
C23 | 0.2868 (3) | −0.1201 (2) | 0.40322 (18) | 0.0542 (8) | |
H23 | 0.3561 | −0.1631 | 0.4068 | 0.065* | |
C24 | 0.1741 (3) | −0.1463 (2) | 0.43669 (19) | 0.0587 (9) | |
H24 | 0.168 | −0.2064 | 0.4633 | 0.07* | |
C25 | 0.0706 (3) | −0.0832 (2) | 0.43052 (19) | 0.0590 (9) | |
H25 | −0.006 | −0.1018 | 0.4517 | 0.071* | |
C26 | 0.0808 (3) | 0.0084 (2) | 0.39263 (18) | 0.0491 (7) | |
H26 | 0.0115 | 0.0515 | 0.3899 | 0.059* | |
C31 | 0.3601 (2) | 0.2017 (2) | 0.32061 (17) | 0.0408 (7) | |
C32 | 0.4207 (3) | 0.2564 (2) | 0.2644 (2) | 0.0519 (8) | |
H32 | 0.3796 | 0.267 | 0.2181 | 0.062* | |
C33 | 0.5417 (3) | 0.2954 (3) | 0.2766 (2) | 0.0675 (10) | |
H33 | 0.582 | 0.3303 | 0.2383 | 0.081* | |
C34 | 0.6009 (3) | 0.2820 (3) | 0.3452 (3) | 0.0773 (12) | |
H34 | 0.6821 | 0.3075 | 0.3533 | 0.093* | |
C35 | 0.5414 (3) | 0.2311 (3) | 0.4027 (2) | 0.0761 (11) | |
H35 | 0.5816 | 0.224 | 0.4496 | 0.091* | |
C36 | 0.4205 (3) | 0.1902 (3) | 0.39033 (19) | 0.0575 (8) | |
H36 | 0.3809 | 0.1553 | 0.4289 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Rh | 0.03576 (12) | 0.04226 (14) | 0.03741 (13) | −0.00080 (10) | 0.00261 (9) | −0.00204 (11) |
P | 0.0319 (3) | 0.0413 (4) | 0.0359 (4) | −0.0014 (3) | −0.0019 (3) | 0.0011 (3) |
N | 0.0315 (12) | 0.0480 (15) | 0.0546 (16) | −0.0036 (10) | 0.0091 (11) | −0.0073 (12) |
O1 | 0.0529 (12) | 0.0564 (13) | 0.0427 (12) | 0.0160 (10) | −0.0064 (10) | −0.0058 (10) |
O2 | 0.117 (2) | 0.0847 (18) | 0.0401 (15) | −0.0191 (16) | −0.0044 (14) | 0.0010 (13) |
C1 | 0.0410 (16) | 0.057 (2) | 0.067 (2) | −0.0048 (15) | 0.0137 (16) | −0.0148 (17) |
C2 | 0.0472 (19) | 0.063 (2) | 0.101 (3) | −0.0021 (17) | 0.022 (2) | −0.028 (2) |
C3 | 0.0369 (17) | 0.050 (2) | 0.120 (4) | 0.0048 (15) | 0.009 (2) | −0.010 (2) |
C4 | 0.0284 (15) | 0.051 (2) | 0.089 (3) | 0.0013 (14) | −0.0021 (16) | 0.0024 (18) |
C5 | 0.0464 (19) | 0.064 (2) | 0.108 (4) | 0.0093 (17) | −0.016 (2) | 0.014 (2) |
C6 | 0.053 (2) | 0.090 (3) | 0.081 (3) | 0.004 (2) | −0.021 (2) | 0.018 (2) |
C7 | 0.0528 (19) | 0.079 (2) | 0.053 (2) | 0.0080 (17) | −0.0103 (16) | 0.0008 (18) |
C8 | 0.0356 (15) | 0.0517 (18) | 0.0510 (19) | −0.0020 (14) | −0.0024 (13) | 0.0003 (15) |
C9 | 0.0290 (14) | 0.0467 (18) | 0.057 (2) | −0.0053 (12) | 0.0028 (13) | 0.0000 (15) |
C10 | 0.0603 (19) | 0.0456 (17) | 0.0446 (19) | −0.0083 (15) | 0.0070 (15) | −0.0027 (15) |
C11 | 0.0340 (14) | 0.0410 (16) | 0.0369 (15) | 0.0029 (12) | −0.0028 (12) | −0.0007 (12) |
C12 | 0.0415 (16) | 0.0555 (19) | 0.056 (2) | 0.0022 (14) | −0.0032 (15) | −0.0100 (15) |
C13 | 0.0539 (19) | 0.072 (2) | 0.059 (2) | 0.0059 (16) | −0.0146 (17) | −0.0112 (18) |
C14 | 0.068 (2) | 0.079 (2) | 0.049 (2) | 0.0099 (19) | −0.0146 (17) | −0.0181 (17) |
C15 | 0.0575 (19) | 0.069 (2) | 0.0449 (19) | 0.0132 (17) | 0.0046 (16) | −0.0037 (16) |
C16 | 0.0406 (15) | 0.0566 (19) | 0.0455 (18) | 0.0079 (14) | 0.0000 (14) | −0.0042 (14) |
C21 | 0.0380 (14) | 0.0417 (16) | 0.0375 (16) | −0.0047 (12) | −0.0016 (12) | 0.0004 (12) |
C22 | 0.0440 (16) | 0.0513 (19) | 0.0454 (18) | 0.0032 (14) | −0.0004 (14) | 0.0032 (14) |
C23 | 0.061 (2) | 0.050 (2) | 0.052 (2) | 0.0116 (15) | −0.0054 (16) | 0.0035 (15) |
C24 | 0.078 (2) | 0.0427 (18) | 0.056 (2) | −0.0027 (17) | 0.0042 (18) | 0.0061 (15) |
C25 | 0.060 (2) | 0.052 (2) | 0.065 (2) | −0.0073 (16) | 0.0165 (17) | 0.0078 (17) |
C26 | 0.0427 (16) | 0.0496 (19) | 0.055 (2) | 0.0008 (14) | 0.0045 (14) | 0.0024 (15) |
C31 | 0.0350 (14) | 0.0406 (16) | 0.0467 (18) | −0.0028 (12) | −0.0042 (13) | −0.0006 (13) |
C32 | 0.0440 (16) | 0.0523 (19) | 0.059 (2) | −0.0043 (14) | −0.0035 (15) | 0.0080 (15) |
C33 | 0.050 (2) | 0.059 (2) | 0.094 (3) | −0.0121 (16) | 0.011 (2) | 0.008 (2) |
C34 | 0.0377 (18) | 0.074 (3) | 0.119 (4) | −0.0171 (18) | −0.012 (2) | 0.003 (2) |
C35 | 0.055 (2) | 0.085 (3) | 0.086 (3) | −0.012 (2) | −0.031 (2) | 0.005 (2) |
C36 | 0.0498 (18) | 0.066 (2) | 0.057 (2) | −0.0096 (16) | −0.0075 (16) | 0.0068 (17) |
Rh—C10 | 1.803 (3) | C13—H13A | 0.97 |
Rh—O1 | 2.060 (2) | C13—H13B | 0.97 |
Rh—N | 2.128 (2) | C14—C15 | 1.525 (4) |
Rh—P | 2.2798 (8) | C14—H14A | 0.97 |
P—C21 | 1.838 (3) | C14—H14B | 0.97 |
P—C31 | 1.844 (3) | C15—C16 | 1.532 (4) |
P—C11 | 1.846 (3) | C15—H15A | 0.97 |
N—C1 | 1.338 (4) | C15—H15B | 0.97 |
N—C9 | 1.375 (4) | C16—H16A | 0.97 |
O1—C8 | 1.328 (3) | C16—H16B | 0.97 |
O2—C10 | 1.161 (4) | C21—C26 | 1.390 (4) |
C1—C2 | 1.410 (5) | C21—C22 | 1.408 (4) |
C1—H1 | 0.93 | C22—C23 | 1.378 (4) |
C2—C3 | 1.364 (5) | C22—H22 | 0.93 |
C2—H2 | 0.93 | C23—C24 | 1.383 (4) |
C3—C4 | 1.410 (5) | C23—H23 | 0.93 |
C3—H3 | 0.93 | C24—C25 | 1.381 (4) |
C4—C5 | 1.408 (5) | C24—H24 | 0.93 |
C4—C9 | 1.424 (4) | C25—C26 | 1.395 (4) |
C5—C6 | 1.369 (5) | C25—H25 | 0.93 |
C5—H5 | 0.93 | C26—H26 | 0.93 |
C6—C7 | 1.421 (5) | C31—C36 | 1.385 (4) |
C6—H6 | 0.93 | C31—C32 | 1.395 (4) |
C7—C8 | 1.392 (4) | C32—C33 | 1.393 (4) |
C7—H7 | 0.93 | C32—H32 | 0.93 |
C8—C9 | 1.432 (4) | C33—C34 | 1.364 (5) |
C11—C16 | 1.536 (4) | C33—H33 | 0.93 |
C11—C12 | 1.549 (4) | C34—C35 | 1.380 (6) |
C11—H11 | 0.98 | C34—H34 | 0.93 |
C12—C13 | 1.527 (4) | C35—C36 | 1.402 (4) |
C12—H12A | 0.97 | C35—H35 | 0.93 |
C12—H12B | 0.97 | C36—H36 | 0.93 |
C13—C14 | 1.523 (4) | ||
C10—Rh—O1 | 177.29 (11) | C12—C13—H13A | 109.4 |
C10—Rh—N | 99.10 (12) | C14—C13—H13B | 109.4 |
O1—Rh—N | 79.41 (9) | C12—C13—H13B | 109.4 |
C10—Rh—P | 88.70 (10) | H13A—C13—H13B | 108 |
O1—Rh—P | 93.11 (6) | C13—C14—C15 | 111.1 (3) |
N—Rh—P | 168.64 (7) | C13—C14—H14A | 109.4 |
C21—P—C31 | 104.24 (12) | C15—C14—H14A | 109.4 |
C21—P—C11 | 104.35 (12) | C13—C14—H14B | 109.4 |
C31—P—C11 | 106.25 (13) | C15—C14—H14B | 109.4 |
C21—P—Rh | 118.42 (9) | H14A—C14—H14B | 108 |
C31—P—Rh | 112.15 (9) | C14—C15—C16 | 111.5 (3) |
C11—P—Rh | 110.48 (9) | C14—C15—H15A | 109.3 |
C1—N—C9 | 118.8 (3) | C16—C15—H15A | 109.3 |
C1—N—Rh | 129.4 (2) | C14—C15—H15B | 109.3 |
C9—N—Rh | 111.47 (18) | C16—C15—H15B | 109.3 |
C8—O1—Rh | 113.83 (18) | H15A—C15—H15B | 108 |
N—C1—C2 | 121.8 (3) | C15—C16—C11 | 109.6 (2) |
N—C1—H1 | 119.1 | C15—C16—H16A | 109.8 |
C2—C1—H1 | 119.1 | C11—C16—H16A | 109.8 |
C3—C2—C1 | 119.6 (3) | C15—C16—H16B | 109.8 |
C3—C2—H2 | 120.2 | C11—C16—H16B | 109.8 |
C1—C2—H2 | 120.2 | H16A—C16—H16B | 108.2 |
C2—C3—C4 | 120.8 (3) | C26—C21—C22 | 118.3 (3) |
C2—C3—H3 | 119.6 | C26—C21—P | 118.9 (2) |
C4—C3—H3 | 119.6 | C22—C21—P | 122.7 (2) |
C5—C4—C3 | 125.3 (3) | C23—C22—C21 | 120.7 (3) |
C5—C4—C9 | 118.3 (3) | C23—C22—H22 | 119.7 |
C3—C4—C9 | 116.4 (3) | C21—C22—H22 | 119.7 |
C6—C5—C4 | 120.0 (3) | C22—C23—C24 | 120.3 (3) |
C6—C5—H5 | 120 | C22—C23—H23 | 119.8 |
C4—C5—H5 | 120 | C24—C23—H23 | 119.8 |
C5—C6—C7 | 122.0 (4) | C25—C24—C23 | 120.0 (3) |
C5—C6—H6 | 119 | C25—C24—H24 | 120 |
C7—C6—H6 | 119 | C23—C24—H24 | 120 |
C8—C7—C6 | 120.2 (3) | C24—C25—C26 | 120.0 (3) |
C8—C7—H7 | 119.9 | C24—C25—H25 | 120 |
C6—C7—H7 | 119.9 | C26—C25—H25 | 120 |
O1—C8—C7 | 123.4 (3) | C21—C26—C25 | 120.7 (3) |
O1—C8—C9 | 119.1 (3) | C21—C26—H26 | 119.7 |
C7—C8—C9 | 117.5 (3) | C25—C26—H26 | 119.7 |
N—C9—C4 | 122.5 (3) | C36—C31—C32 | 118.7 (3) |
N—C9—C8 | 115.7 (3) | C36—C31—P | 121.1 (2) |
C4—C9—C8 | 121.8 (3) | C32—C31—P | 120.1 (2) |
O2—C10—Rh | 179.6 (3) | C33—C32—C31 | 121.0 (3) |
C16—C11—C12 | 109.4 (2) | C33—C32—H32 | 119.5 |
C16—C11—P | 118.41 (19) | C31—C32—H32 | 119.5 |
C12—C11—P | 109.19 (19) | C34—C33—C32 | 119.7 (3) |
C16—C11—H11 | 106.4 | C34—C33—H33 | 120.2 |
C12—C11—H11 | 106.4 | C32—C33—H33 | 120.2 |
P—C11—H11 | 106.4 | C33—C34—C35 | 120.6 (3) |
C13—C12—C11 | 110.6 (3) | C33—C34—H34 | 119.7 |
C13—C12—H12A | 109.5 | C35—C34—H34 | 119.7 |
C11—C12—H12A | 109.5 | C34—C35—C36 | 120.1 (4) |
C13—C12—H12B | 109.5 | C34—C35—H35 | 120 |
C11—C12—H12B | 109.5 | C36—C35—H35 | 120 |
H12A—C12—H12B | 108.1 | C31—C36—C35 | 120.0 (3) |
C14—C13—C12 | 111.1 (2) | C31—C36—H36 | 120 |
C14—C13—H13A | 109.4 | C35—C36—H36 | 120 |
O1—Rh—P—C11 | −2.40 (11) | O1—Rh—P—C13 | −21.04 (8) |
O1—Rh—P—C12 | −32.02 (9) |
PR3 | Rh—P | Rh—N | Rh—O | N—Rh—O | ΘE(Å) | 1JRh-P(Hz) |
PPh2Cyi | 2.279 (1) | 2.128 (2) | 2.060 (2) | 79.41 (9) | 151 | 163 |
PPh3ii | 2.261 (2) | 2.098 (9) | 2.042 (5) | 80.0 (3) | 153 | 161 |
P(OPh)3iii | 2.186 (1) | 2.097 (2) | 2.022 (2) | 80.8iv | 154 | 281 |
PPh3v | 2.317 (2) | 2.084 (7) | 2.037 (4) | 81.2 (2) | 153 | 163 |
P(O2,6DMP)3vi | 2.198 (1) | 2.091 (3) | 2.029 (3) | 80.3 (1) | 183 | 280 |
References and notes: (i) this work, Ph2Cy = cyclohexyldiphenyl; (ii) Leipoldt et al. (1981); (iii) Simanko et al. (2000); (iv) data extracted from the Cambridge Structural Database (Version 5.26), no s.u. values (Allen, 2002); (v) van Aswegen et al. (1991); RhIII iodomethane oxidative addition product containing apical trans methyl and iodo ligands; (vi) Janse van Rensburg et al. (2005). |
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