Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000077/wn6068sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000077/wn6068Isup2.hkl |
CCDC reference: 180758
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.011 Å
- R factor = 0.036
- wR factor = 0.046
- Data-to-parameter ratio = 10.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
DIFF_012 Alert A _diffrn_reflns_av_R_equivalents is missing R factor for symmetry-equivalent intensities. The following tests will not be performed RINTA SHFSU_01 Alert A The absolute value of parameter shift to su ratio > 0.20 Absolute value of the parameter shift to su ratio given 0.280 Additional refinement cycles may be required.
Alert Level C:
GOODF_01 Alert C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 2.180 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.25 From the CIF: _reflns_number_total 3170 Count of symmetry unique reflns 3152 Completeness (_total/calc) 100.57% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 18 Fraction of Friedel pairs measured 0.006 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: KRISEL control software [Any reference?]; cell refinement: MolEN (Enraf-Nonius, 1990); data reduction: MolEN; program(s) used to solve structure: MolEN; program(s) used to refine structure: MolEN; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: Word Pad, IUCR CIF Template.
[RhCl(C8H12)(C18H15P)] | Dx = 1.50 Mg m−3 |
Mr = 508.84 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 17 reflections |
a = 16.246 (3) Å | θ = 10.0–20.5° |
b = 8.145 (2) Å | µ = 0.96 mm−1 |
c = 16.992 (4) Å | T = 296 K |
V = 2248 (1) Å3 | Irregular, brown |
Z = 4 | 0.29 × 0.28 × 0.28 mm |
F(000) = 1040.0 |
Picker four-circle diffractometer | θmax = 28.3°, θmin = 1.0° |
Radiation source: x-ray tube | h = 0→21 |
Grahpite monochromator | k = 0→10 |
ω–2θ scans | l = 0→22 |
3170 measured reflections | 3 standard reflections every 120 min |
3170 independent reflections | intensity decay: none |
2839 reflections with I > 2σ(I) |
Refinement on F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.046 | Weighting scheme based on measured s.u.'s w = 4F2/[σ2(F2) + (0.03F2)2] |
S = 2.18 | (Δ/σ)max = 0.28 |
2839 reflections | Δρmax = 0.46 e Å−3 |
262 parameters | Δρmin = −0.12 e Å−3 |
Refinement. The structure for this molecule was refined several years ago using a mainframe computer. Because cycles of refinment on the mainframe were so time consuming, refinment on this molecule was stopped when the the largest ratio of the refinment shift to standard uncertaintly was equal to 0.28. The MolEN program which was used for refinment is no longer available for our use. |
x | y | z | Uiso*/Ueq | ||
RH1 | 0.63038 (3) | 0.10595 (6) | 0.11040 (3) | 0.1662 | |
CL1 | 0.6358 (1) | 0.3708 (2) | 0.1666 (1) | 0.2107 | |
P1 | 0.5951 (1) | 0.2265 (2) | −0.00778 (9) | 0.4970 | |
C1 | 0.5787 (4) | −0.1265 (8) | 0.0787 (4) | 0.1847 | |
C2 | 0.6643 (4) | −0.1261 (8) | 0.0659 (4) | 0.1950 | |
C3 | 0.7016 (5) | 0.0202 (9) | 0.2130 (4) | 0.2047 | |
C4 | 0.6220 (5) | −0.0074 (9) | 0.2301 (4) | 0.2093 | |
C5 | 0.5801 (5) | −0.176 (1) | 0.2277 (4) | 0.2223 | |
C6 | 0.5343 (5) | −0.200 (1) | 0.1477 (5) | 0.2197 | |
C7 | 0.7252 (5) | −0.2189 (9) | 0.1175 (5) | 0.2103 | |
C8 | 0.7635 (5) | −0.108 (1) | 0.1818 (5) | 0.2273 | |
C11 | 0.5088 (4) | 0.3637 (7) | 0.0064 (4) | 0.1717 | |
C12 | 0.4999 (5) | 0.5114 (9) | −0.0334 (4) | 0.2100 | |
C13 | 0.4288 (5) | 0.606 (1) | −0.0215 (5) | 0.2197 | |
C14 | 0.3689 (5) | 0.555 (1) | 0.0314 (5) | 0.2287 | |
C15 | 0.3774 (4) | 0.407 (1) | 0.0724 (4) | 0.2097 | |
C16 | 0.4479 (4) | 0.3156 (9) | 0.0597 (4) | 0.1907 | |
C21 | 0.5595 (4) | 0.0923 (8) | −0.0877 (3) | 0.1797 | |
C22 | 0.4758 (4) | 0.0788 (9) | −0.1080 (4) | 0.1960 | |
C23 | 0.4519 (5) | −0.034 (1) | −0.1636 (5) | 0.2350 | |
C24 | 0.5066 (6) | −0.135 (1) | −0.2020 (5) | 0.2493 | |
C25 | 0.5903 (6) | −0.122 (1) | −0.1824 (5) | 0.2390 | |
C26 | 0.6166 (5) | −0.0095 (9) | −0.1258 (4) | 0.2083 | |
C31 | 0.6738 (4) | 0.3503 (8) | −0.0565 (4) | 0.1733 | |
C32 | 0.7407 (4) | 0.4105 (9) | −0.0130 (4) | 0.1963 | |
C33 | 0.7992 (5) | 0.5057 (9) | −0.0492 (4) | 0.2100 | |
C34 | 0.7954 (5) | 0.543 (1) | −0.1297 (5) | 0.2160 | |
C35 | 0.7282 (5) | 0.481 (1) | −0.1732 (5) | 0.2173 | |
C36 | 0.6696 (4) | 0.386 (1) | −0.1364 (4) | 0.2000 | |
H1 | 0.542 | 0.548 | −0.068 | 0.2414* | |
H2 | 0.422 | 0.705 | −0.050 | 0.2516* | |
H3 | 0.322 | 0.622 | 0.040 | 0.2639* | |
H4 | 0.336 | 0.371 | 0.108 | 0.2414* | |
H5 | 0.455 | 0.216 | 0.088 | 0.2165* | |
H6 | 0.436 | 0.147 | −0.084 | 0.2306* | |
H7 | 0.395 | −0.043 | −0.176 | 0.2735* | |
H8 | 0.488 | −0.212 | −0.240 | 0.2891* | |
H9 | 0.629 | −0.189 | −0.208 | 0.2779* | |
H10 | 0.673 | −0.002 | −0.113 | 0.2387* | |
H11 | 0.745 | 0.385 | 0.041 | 0.2279* | |
H12 | 0.844 | 0.548 | −0.019 | 0.2387* | |
H13 | 0.837 | 0.608 | −0.154 | 0.2466* | |
H14 | 0.723 | 0.505 | −0.228 | 0.2516* | |
H15 | 0.625 | 0.344 | −0.166 | 0.2306* | |
H16 | 0.542 | −0.184 | 0.270 | 0.2591* | |
H17 | 0.621 | −0.259 | 0.233 | 0.2591* | |
H18 | 0.528 | −0.314 | 0.139 | 0.2566* | |
H19 | 0.482 | −0.149 | 0.152 | 0.2566* | |
H20 | 0.768 | −0.261 | 0.085 | 0.2414* | |
H21 | 0.697 | −0.307 | 0.142 | 0.2414* | |
H22 | 0.781 | −0.174 | 0.224 | 0.2615* | |
H23 | 0.809 | −0.052 | 0.160 | 0.2615* | |
H24 | 0.546 | −0.075 | 0.040 | 0.2135* | |
H25 | 0.685 | −0.065 | 0.023 | 0.2251* | |
H26 | 0.722 | 0.129 | 0.221 | 0.2387* | |
H27 | 0.589 | 0.084 | 0.245 | 0.2466* |
U11 | U22 | U33 | U12 | U13 | U23 | |
RH1 | 0.0339 (2) | 0.0227 (2) | 0.0261 (2) | −0.0008 (2) | −0.0023 (2) | −0.0005 (2) |
CL1 | 0.071 (1) | 0.0277 (7) | 0.0410 (7) | −0.0025 (9) | −0.0083 (9) | −0.0071 (6) |
P1 | 0.0296 (7) | 0.0251 (7) | 0.0278 (7) | −0.0025 (7) | −0.0015 (7) | 0.0002 (6) |
C1 | 0.044 (3) | 0.022 (3) | 0.039 (3) | −0.006 (3) | −0.000 (3) | −0.002 (3) |
C2 | 0.045 (3) | 0.030 (3) | 0.042 (3) | 0.004 (3) | 0.007 (3) | −0.008 (3) |
C3 | 0.055 (4) | 0.045 (4) | 0.031 (3) | 0.009 (4) | −0.008 (3) | 0.009 (3) |
C4 | 0.066 (4) | 0.049 (4) | 0.024 (3) | 0.005 (4) | −0.007 (3) | 0.010 (3) |
C5 | 0.068 (5) | 0.051 (4) | 0.034 (3) | −0.007 (4) | 0.005 (4) | 0.012 (3) |
C6 | 0.045 (4) | 0.051 (4) | 0.056 (4) | −0.018 (3) | 0.000 (3) | 0.019 (4) |
C7 | 0.048 (4) | 0.033 (3) | 0.053 (4) | 0.007 (3) | −0.004 (4) | 0.001 (4) |
C8 | 0.044 (4) | 0.047 (4) | 0.066 (4) | 0.008 (4) | −0.011 (3) | 0.000 (5) |
C11 | 0.031 (3) | 0.024 (3) | 0.035 (3) | −0.001 (2) | −0.001 (3) | −0.003 (2) |
C12 | 0.052 (4) | 0.034 (3) | 0.047 (4) | 0.002 (3) | −0.002 (3) | 0.000 (3) |
C13 | 0.045 (3) | 0.041 (4) | 0.061 (4) | 0.008 (4) | −0.002 (3) | 0.009 (4) |
C14 | 0.042 (3) | 0.051 (4) | 0.067 (5) | 0.008 (4) | −0.009 (4) | −0.008 (4) |
C15 | 0.036 (3) | 0.049 (4) | 0.049 (3) | 0.007 (4) | 0.002 (3) | −0.008 (3) |
C16 | 0.036 (3) | 0.038 (3) | 0.035 (3) | 0.002 (3) | 0.002 (3) | −0.001 (3) |
C21 | 0.038 (3) | 0.030 (3) | 0.030 (3) | −0.009 (3) | −0.003 (2) | 0.003 (3) |
C22 | 0.045 (3) | 0.045 (4) | 0.031 (3) | −0.009 (3) | −0.019 (3) | 0.005 (3) |
C23 | 0.062 (5) | 0.055 (4) | 0.055 (4) | −0.018 (4) | −0.016 (4) | −0.005 (4) |
C24 | 0.081 (5) | 0.060 (5) | 0.051 (4) | −0.009 (5) | −0.013 (4) | −0.011 (4) |
C25 | 0.074 (5) | 0.057 (5) | 0.048 (4) | −0.011 (5) | 0.004 (4) | −0.022 (4) |
C26 | 0.056 (4) | 0.044 (3) | 0.033 (3) | −0.004 (3) | 0.000 (3) | −0.008 (3) |
C31 | 0.030 (3) | 0.029 (3) | 0.032 (3) | −0.001 (3) | 0.002 (3) | 0.001 (3) |
C32 | 0.037 (3) | 0.030 (3) | 0.052 (4) | −0.006 (3) | −0.000 (3) | −0.005 (3) |
C33 | 0.048 (4) | 0.042 (4) | 0.043 (4) | −0.006 (3) | 0.002 (3) | −0.003 (3) |
C34 | 0.046 (4) | 0.040 (4) | 0.055 (4) | −0.005 (3) | 0.006 (3) | 0.005 (4) |
C35 | 0.052 (4) | 0.043 (4) | 0.051 (4) | −0.013 (4) | 0.011 (3) | 0.006 (4) |
C36 | 0.035 (3) | 0.050 (4) | 0.039 (3) | −0.012 (4) | 0.002 (3) | 0.006 (3) |
RH1—CL1 | 2.361 (2) | C34—C35 | 1.41 (1) |
C11—C16 | 1.396 (9) | C7—C8 | 1.55 (1) |
RH1—P1 | 2.308 (2) | C35—C36 | 1.38 (1) |
C12—C13 | 1.40 (1) | C11—C12 | 1.388 (9) |
RH1—C1 | 2.140 (6) | C1—H24 | 0.944 |
C13—C14 | 1.39 (1) | C2—H25 | 0.945 |
RH1—C2 | 2.109 (7) | C3—H26 | 0.956 |
C14—C15 | 1.40 (1) | C4—H27 | 0.952 |
RH1—C3 | 2.205 (7) | C5—H16 | 0.951 |
C15—C16 | 1.38 (1) | C5—H17 | 0.952 |
RH1—C4 | 2.238 (7) | C6—H18 | 0.946 |
C21—C22 | 1.406 (9) | C6—H19 | 0.949 |
P1—C11 | 1.809 (6) | C7—H21 | 0.948 |
C21—C26 | 1.40 (1) | C7—H20 | 0.952 |
P1—C21 | 1.837 (6) | C8—H22 | 0.940 |
C22—C23 | 1.37 (1) | C8—H23 | 0.944 |
P1—C31 | 1.827 (6) | C12—H1 | 0.950 |
C23—C24 | 1.38 (1) | C13—H2 | 0.947 |
C1—C2 | 1.41 (1) | C14—H3 | 0.949 |
C24—C25 | 1.40 (1) | C15—H4 | 0.951 |
C1—C6 | 1.50 (1) | C16—H5 | 0.950 |
C25—C26 | 1.39 (1) | C22—H6 | 0.945 |
C2—C7 | 1.52 (1) | C23—H7 | 0.951 |
C31—C32 | 1.402 (9) | C24—H8 | 0.950 |
C3—C4 | 1.34 (1) | C25—H9 | 0.939 |
C31—C36 | 1.390 (9) | C26—H10 | 0.944 |
C3—C8 | 1.54 (1 | C32—H11 | 0.943 |
C32—C33 | 1.37 (1) | C33—H12 | 0.955 |
C4—C5 | 1.53 (1) | C34—H13 | 0.953 |
C33—C34 | 1.40 (1) | C35—H14 | 0.955 |
C5—C6 | 1.56 (1) | C36—H15 | 0.946 |
CL1—RH1—P1 | 88.44 (6) | H25—C2—C1 | 118.18 |
RH1—C1—C6 | 110.1 (5) | H25—C2—C7 | 118.33 |
CL1—RH1—C1 | 157.7 (2) | H26—C3—C4 | 117.25 |
C2—C1—C6 | 126.7 (6) | H26—C3—C8 | 116.75 |
CL1—RH1—C2 | 162.6 (2) | H27—C4—C3 | 117.94 |
RH1—C2—C1 | 71.9 (4) | H27—C4—C5 | 117.23 |
CL1—RH1—C3 | 87.1 (2) | H16—C5—H17 | 109.52 |
RH1—C2—C7 | 114.1 (5) | H16—C5—C4 | 109.29 |
CL1—RH1—C4 | 90.7 (2) | H16—C5—C6 | 109.83 |
C1—C2—C7 | 123.4 (6) | H17—C5—C4 | 108.88 |
P1—RH1—C1 | 93.4 (2) | H17—C5—C6 | 109.02 |
RH1—C3—C4 | 73.7 (4) | H18—C6—H19 | 110.18 |
P1—RH1—C2 | 97.7 (2) | H18—C6—C1 | 108.75 |
RH1—C3—C8 | 106.5 (5) | H18—C6—C5 | 108.09 |
P1—RH1—C3 | 162.3 (2) | H19—C6—C1 | 108.42 |
C4—C3—C8 | 126.1 (7) | H19—C6—C5 | 107.75 |
P1—RH1—C4 | 162.0 (2) | H21—C7—H20 | 109.59 |
RH1—C4—C3 | 71.1 (4) | H21—C7—C2 | 108.34 |
RH1—C4—C5 | 111.9 (4) | H21—C7—C8 | 109.03 |
C3—C4—C5 | 124.8 (7) | H20—C7—C2 | 108.63 |
C4—C5—C6 | 110.2 (6) | H20—C7—C8 | 109.03 |
C1—C6—C5 | 113.7 (6) | H22—C8—H23 | 109.79 |
C2—C7—C8 | 112.1 (6) | H22—C8—C3 | 108.77 |
C3—C8—C7 | 112.0 (6) | H22—C8—C7 | 109.04 |
RH1—P1—C11 | 109.8 (2) | H23—C8—C3 | 108.54 |
P1—C11—C12 | 123.4 (5) | H23—C8—C7 | 108.64 |
RH1—P1—C21 | 118.0 (2) | H1—C12—C11 | 119.91 |
P1—C11—C16 | 117.5 (5) | H1—C12—C13 | 120.64 |
RH1—P1—C31 | 117.1 (2) | H2—C13—C14 | 120.27 |
C12—C11—C16 | 119.1 (6) | H2—C13—C12 | 119.33 |
C11—P1—C21 | 102.8 (3) | H3—C14—C13 | 119.38 |
C11—C12—C13 | 119.3 (7) | H3—C14—C15 | 119.89 |
C11—P1—C31 | 105.2 (3) | H4—C15—C16 | 121.27 |
C12—C13—C14 | 120.6 (8) | H4—C15—C14 | 120.84 |
C21—P1—C31 | 102.4 (3) | H5—C16—C15 | 118.76 |
C13—C14—C15 | 120.6 (7) | H5—C16—C11 | 118.78 |
RH1—C1—C2 | 69.5 (4) | H6—C22—C23 | 119.77 |
C14—C15—C16 | 117.9 (7) | H6—C22—C21 | 120.63 |
C11—C16—C15 | 122.4 (6) | H7—C23—C22 | 118.60 |
P1—C31—C32 | 119.8 (5) | H7—C23—C24 | 118.48 |
P1—C21—C22 | 122.2 (5) | H8—C24—C23 | 120.80 |
P1—C31—C36 | 121.6 (5) | H8—C24—C25 | 121.29 |
P1—C21—C26 | 118.9 (5) | H9—C25—C26 | 119.72 |
C32—C31—C36 | 118.7 (6) | H9—C25—C24 | 119.64 |
C22—C21—C26 | 118.7 (6) | H10—C26—C25 | 119.9 |
C31—C32—C33 | 119.9 (6) | H10—C26—C21 | 119.8 |
C21—C22—C23 | 119.6 (7) | H11—C32—C33 | 120.6 |
C32—C33—C34 | 121.9 (7) | H11—C32—C31 | 119.53 |
C22—C23—C24 | 123.0 (8) | H12—C33—C32 | 119.40 |
C33—C34—C35 | 117.8 (7) | H12—C33—C34 | 118.65 |
C23—C24—C25 | 117.7 (8) | H13—C34—C33 | 120.79 |
C34—C35—C36 | 119.9 (7) | H13—C34—C35 | 121.36 |
C24—C25—C26 | 120.8 (8) | H14—C35—C36 | 119.77 |
C31—C36—C35 | 121.8 (6) | H14—C35—C34 | 120.37 |
C21—C26—C25 | 120.2 (7) | H15—C36—C35 | 119.43 |
H24—C1—C2 | 116.58 | H15—C36—C31 | 118.76 |
H24—C1—C6 | 116.81 |
Compound | Rh—D1 | Rh—D2 | Cl—Rh—D1 | Cl—Rh—D2 | D1—Rh—D2 |
A | 1.986 (6) | 2.013 (6) | 178.1 (2) | 90.8 (2) | 87.7 (3) |
B | 1.989 (5) | 2.026 (5) | 177.9 (2) | 91.9 (2) | 88.2 (2) |
C | 1.978 (5) | 2.001 (5) | 175.9 (2) | 91.9 (1) | 88.0 (2) |
D | 1.987 (8) | 2.118 (6) | 177.5 (5) | 90.9 (3) | 86.8 (4) |
2 | 2.005 (7) | 2.118 (7) | 174.6 (2) | 88.8 (2) | 86.5 (4) |
E | 1.988 (6) | 2.099 (7) | 176.5 (4) | 90.4 (3) | 86.3 (4) |
F | 1.996 (9) | 2.089 (7) | 175.7 (3) | 90.2 (2) | 85.9 (4) |
G | 1.994 (4) | 2.092 (4) | 176.1 (1) | 90.1 (1) | 84.0 (2) |
D1 and D2 are the mid-points of the two double
bonds in cod. A = Rh(cod)Cl(Et3P═N(C6H4)CH3)) (Imhoff et al., 1990). B = RhCl(C8H12)(C9H16N2) (Flörke et al., 1992). C = RhCl(C8H12)(C7H12N2) .1/2C4H8O2 (Flörke et al., 1992). D = RhCl(cod)P(p-C6H4F3)3 (Iglesias et al., 1987). 2 = Title compound RhCl(cod)P(C6H5)3 E = RhCl(cod)P(C6H5)(o-tol) (Hubbard, 1988). F = RhCl(cod)P(C6H5)(o-tol)2 at 252K (Hubbard, 1988). G = RhCl(cod)P(C6H5)(o-tol)2 at 123K (Pinkerton, 1988). |