Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012170/ac6041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012170/ac6041Isup2.hkl |
CCDC reference: 217363
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.015 Å
- R factor = 0.040
- wR factor = 0.046
- Data-to-parameter ratio = 9.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.314 0.654 Tmin' and Tmax expected: 0.400 0.654 RR' = 0.785 Please check that your absorption correction is appropriate. REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.78 From the CIF: _reflns_number_total 8337 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 9165 Completeness (_total/calc) 90.97% Alert C: < 95% complete REFNR_01 Alert C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.5897 Proportion of unique data used 0.7009 Ratio reflections to parameters 9.5318 THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5897 PLAT_213 Alert C Atom has ADP max/min Ratio ............. 3.10 C5
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
5 Alert Level C = Please check
The title compound was prepared by stirring the phosphine ligand in a CH2Cl2 solution of IrCp*Cl2 dimer at room temperature.
Data collection: SMART (Bruker, 1995-1999); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare, 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1985, 1992); molecular graphics: please provide; software used to prepare material for publication: TEXSAN.
Fig. 1. Thermal ellipsoid plot (50% probability) of the asymmetric unit. The H atoms are removed for clarity. |
[Ir(C10H15)(C18H17N2P)Cl2] | Z = 4 |
Mr = 690.67 | F(000) = 1360.00 |
Triclinic, P1 | Dx = 1.721 Mg m−3 |
a = 13.592 (4) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 14.545 (4) Å | Cell parameters from 5533 reflections |
c = 16.427 (4) Å | θ = 5.2–49.5° |
α = 90.018 (4)° | µ = 5.30 mm−1 |
β = 109.683 (4)° | T = 123 K |
γ = 117.455 (4)° | Parallelepiped, orange |
V = 2666 (1) Å3 | 0.17 × 0.09 × 0.08 mm |
SMART CCD diffractometer | 8337 independent reflections |
Radiation source: X-ray tube | 5843 reflections with I > 3.00σ(I) |
Graphite monochromator | Rint = 0.038 |
ω–scan | θmax = 24.8°, θmin = 2.6° |
Absorption correction: multi-scan (Blessing, 1995) | h = 0→15 |
Tmin = 0.314, Tmax = 0.654 | k = −16→14 |
13236 measured reflections | l = −18→17 |
Refinement on F | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | Weighting scheme based on measured s.u.'s Please provide expression for w |
wR(F2) = 0.046 | (Δ/σ)max = 0.001 |
S = 1.23 | Δρmax = 2.16 e Å−3 |
5843 reflections | Δρmin = −2.33 e Å−3 |
613 parameters |
[Ir(C10H15)(C18H17N2P)Cl2] | γ = 117.455 (4)° |
Mr = 690.67 | V = 2666 (1) Å3 |
Triclinic, P1 | Z = 4 |
a = 13.592 (4) Å | Mo Kα radiation |
b = 14.545 (4) Å | µ = 5.30 mm−1 |
c = 16.427 (4) Å | T = 123 K |
α = 90.018 (4)° | 0.17 × 0.09 × 0.08 mm |
β = 109.683 (4)° |
SMART CCD diffractometer | 8337 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 5843 reflections with I > 3.00σ(I) |
Tmin = 0.314, Tmax = 0.654 | Rint = 0.038 |
13236 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.046 | H-atom parameters constrained |
S = 1.23 | Δρmax = 2.16 e Å−3 |
5843 reflections | Δρmin = −2.33 e Å−3 |
613 parameters |
x | y | z | Uiso*/Ueq | ||
Ir1 | 0.62454 (3) | 0.13409 (3) | 0.75731 (2) | 0.0167 | |
Ir2 | 0.36902 (3) | 0.36216 (3) | 0.18745 (2) | 0.0170 | |
Cl1 | 0.7208 (2) | 0.1084 (2) | 0.9022 (1) | 0.0226 | |
Cl2 | 0.6824 (2) | 0.0276 (2) | 0.6931 (2) | 0.0269 | |
Cl3 | 0.2694 (2) | 0.3808 (2) | 0.2781 (2) | 0.0260 | |
Cl4 | 0.3013 (2) | 0.4629 (2) | 0.0892 (2) | 0.0270 | |
P1 | 0.8074 (2) | 0.2767 (2) | 0.7815 (2) | 0.0199 | |
P2 | 0.1906 (2) | 0.2160 (2) | 0.1076 (2) | 0.0184 | |
N1 | 0.8751 (7) | 0.5878 (7) | 0.3172 (5) | 0.0276 | |
N2 | 0.8207 (8) | 0.3324 (7) | 0.2364 (6) | 0.0313 | |
N3 | 0.0988 (8) | −0.0980 (7) | −0.4003 (5) | 0.0260 | |
N4 | 0.2193 (8) | 0.1672 (7) | −0.4437 (5) | 0.0264 | |
C1 | 0.4291 (8) | 0.0258 (7) | 0.6776 (7) | 0.0224 | |
C2 | 0.4811 (9) | 0.1222 (8) | 0.6431 (6) | 0.0215 | |
C3 | 0.5182 (8) | 0.2112 (8) | 0.7097 (6) | 0.0222 | |
C4 | 0.5013 (8) | 0.1697 (7) | 0.7847 (6) | 0.0187 | |
C5 | 0.4427 (8) | 0.0558 (7) | 0.7631 (6) | 0.0179 | |
C6 | 0.375 (1) | −0.0825 (8) | 0.6267 (7) | 0.0349 | |
C7 | 0.4792 (10) | 0.1266 (10) | 0.5523 (7) | 0.0323 | |
C8 | 0.5531 (10) | 0.3189 (8) | 0.6943 (7) | 0.0309 | |
C9 | 0.5189 (9) | 0.2298 (8) | 0.8675 (7) | 0.0266 | |
C10 | 0.4063 (9) | −0.0154 (8) | 0.8262 (7) | 0.0276 | |
C11 | 0.8562 (9) | 0.3798 (8) | 0.8720 (6) | 0.0270 | |
C12 | 0.9301 (9) | 0.2482 (9) | 0.8115 (7) | 0.0350 | |
C13 | 0.8203 (8) | 0.3430 (7) | 0.6881 (6) | 0.0201 | |
C14 | 0.8428 (10) | 0.4460 (8) | 0.6899 (6) | 0.0280 | |
C15 | 0.8529 (10) | 0.4927 (8) | 0.6174 (7) | 0.0290 | |
C16 | 0.8438 (9) | 0.4393 (8) | 0.5425 (6) | 0.0218 | |
C17 | 0.8207 (9) | 0.3369 (8) | 0.5414 (6) | 0.0268 | |
C18 | 0.8080 (10) | 0.2883 (8) | 0.6126 (7) | 0.0312 | |
C19 | 0.8579 (8) | 0.4918 (8) | 0.4655 (6) | 0.0208 | |
C20 | 0.8914 (9) | 0.5990 (9) | 0.4687 (6) | 0.0306 | |
C21 | 0.8966 (9) | 0.6411 (8) | 0.3938 (7) | 0.0284 | |
C22 | 0.8473 (8) | 0.4856 (8) | 0.3160 (6) | 0.0230 | |
C23 | 0.8365 (9) | 0.4348 (8) | 0.3861 (7) | 0.0226 | |
C24 | 0.8284 (8) | 0.4274 (8) | 0.2324 (6) | 0.0189 | |
C25 | 0.8238 (9) | 0.4711 (8) | 0.1576 (7) | 0.0297 | |
C26 | 0.8101 (10) | 0.4144 (9) | 0.0824 (7) | 0.0290 | |
C27 | 0.8016 (9) | 0.3185 (8) | 0.0841 (7) | 0.0265 | |
C28 | 0.809 (1) | 0.2808 (10) | 0.1618 (7) | 0.0385 | |
C29 | 0.5600 (8) | 0.4766 (8) | 0.2145 (7) | 0.0232 | |
C30 | 0.5142 (9) | 0.3812 (8) | 0.1529 (6) | 0.0252 | |
C31 | 0.4859 (8) | 0.2964 (8) | 0.1977 (6) | 0.0181 | |
C32 | 0.5008 (9) | 0.3346 (8) | 0.2848 (6) | 0.0216 | |
C33 | 0.5525 (8) | 0.4491 (8) | 0.2952 (7) | 0.0273 | |
C34 | 0.6099 (9) | 0.5871 (8) | 0.1942 (7) | 0.0289 | |
C35 | 0.5115 (10) | 0.3764 (9) | 0.0593 (7) | 0.0343 | |
C36 | 0.4604 (9) | 0.1885 (8) | 0.1669 (7) | 0.0277 | |
C37 | 0.4907 (9) | 0.2773 (8) | 0.3585 (6) | 0.0232 | |
C38 | 0.5865 (10) | 0.5210 (9) | 0.3760 (7) | 0.0332 | |
C39 | 0.1477 (8) | 0.1061 (8) | 0.1658 (6) | 0.0236 | |
C40 | 0.0619 (8) | 0.2367 (8) | 0.0725 (6) | 0.0236 | |
C41 | 0.1828 (8) | 0.1589 (7) | 0.0056 (6) | 0.0179 | |
C42 | 0.1720 (8) | 0.2084 (7) | −0.0677 (6) | 0.0216 | |
C43 | 0.1597 (9) | 0.1612 (8) | −0.1478 (6) | 0.0226 | |
C44 | 0.1621 (8) | 0.0675 (8) | −0.1544 (6) | 0.0147 | |
C45 | 0.1809 (8) | 0.0215 (7) | −0.0795 (6) | 0.0187 | |
C46 | 0.1887 (8) | 0.0661 (7) | −0.0013 (6) | 0.0180 | |
C47 | 0.1404 (8) | 0.0119 (8) | −0.2402 (6) | 0.0190 | |
C48 | 0.1698 (8) | 0.0647 (8) | −0.3058 (6) | 0.0176 | |
C49 | 0.1448 (9) | 0.0080 (9) | −0.3861 (6) | 0.0250 | |
C50 | 0.0714 (9) | −0.1475 (8) | −0.3370 (7) | 0.0301 | |
C51 | 0.0877 (9) | −0.0982 (8) | −0.2576 (6) | 0.0226 | |
C52 | 0.1694 (9) | 0.0611 (8) | −0.4590 (6) | 0.0229 | |
C53 | 0.2358 (10) | 0.2142 (9) | −0.5120 (7) | 0.0349 | |
C54 | 0.2069 (9) | 0.1611 (9) | −0.5949 (6) | 0.0264 | |
C55 | 0.1563 (9) | 0.0531 (8) | −0.6083 (6) | 0.0253 | |
C56 | 0.1361 (8) | 0.0018 (8) | −0.5401 (6) | 0.0239 | |
H1 | 0.3092 | −0.0937 | 0.5743 | 0.0419* | |
H2 | 0.3462 | −0.1332 | 0.6613 | 0.0419* | |
H3 | 0.4328 | −0.0892 | 0.6118 | 0.0419* | |
H4 | 0.5194 | 0.0918 | 0.5416 | 0.0388* | |
H5 | 0.5183 | 0.1978 | 0.5460 | 0.0388* | |
H6 | 0.3985 | 0.0921 | 0.5113 | 0.0388* | |
H7 | 0.6202 | 0.3444 | 0.6774 | 0.0370* | |
H8 | 0.5737 | 0.3632 | 0.7465 | 0.0370* | |
H9 | 0.4881 | 0.3194 | 0.6484 | 0.0370* | |
H10 | 0.5993 | 0.2851 | 0.8934 | 0.0319* | |
H11 | 0.5016 | 0.1834 | 0.9077 | 0.0319* | |
H12 | 0.4662 | 0.2584 | 0.8537 | 0.0319* | |
H13 | 0.3687 | −0.0868 | 0.7984 | 0.0331* | |
H14 | 0.3521 | −0.0041 | 0.8434 | 0.0331* | |
H15 | 0.4754 | −0.0001 | 0.8768 | 0.0331* | |
H16 | 0.9293 | 0.4388 | 0.8757 | 0.0324* | |
H17 | 0.8679 | 0.3537 | 0.9255 | 0.0324* | |
H18 | 0.7968 | 0.4002 | 0.8620 | 0.0324* | |
H19 | 0.9127 | 0.1946 | 0.7673 | 0.0420* | |
H20 | 0.9402 | 0.2248 | 0.8661 | 0.0420* | |
H21 | 1.0016 | 0.3102 | 0.8165 | 0.0420* | |
H22 | 0.8507 | 0.4845 | 0.7406 | 0.0336* | |
H23 | 0.8664 | 0.5630 | 0.6189 | 0.0348* | |
H24 | 0.8131 | 0.2984 | 0.4908 | 0.0321* | |
H25 | 0.7908 | 0.2170 | 0.6099 | 0.0374* | |
H26 | 0.9102 | 0.6420 | 0.5213 | 0.0367* | |
H27 | 0.9170 | 0.7131 | 0.3966 | 0.0341* | |
H28 | 0.8149 | 0.3622 | 0.3810 | 0.0272* | |
H29 | 0.8297 | 0.5387 | 0.1573 | 0.0356* | |
H30 | 0.8071 | 0.4434 | 0.0303 | 0.0347* | |
H31 | 0.7908 | 0.2777 | 0.0335 | 0.0318* | |
H32 | 0.8049 | 0.2140 | 0.1631 | 0.0462* | |
H33 | 0.6914 | 0.6287 | 0.2328 | 0.0347* | |
H34 | 0.5649 | 0.6181 | 0.2021 | 0.0347* | |
H35 | 0.6048 | 0.5838 | 0.1350 | 0.0347* | |
H36 | 0.5342 | 0.4445 | 0.0442 | 0.0411* | |
H37 | 0.4326 | 0.3280 | 0.0194 | 0.0411* | |
H38 | 0.5656 | 0.3542 | 0.0556 | 0.0411* | |
H39 | 0.3927 | 0.1576 | 0.1128 | 0.0332* | |
H40 | 0.4439 | 0.1461 | 0.2097 | 0.0332* | |
H41 | 0.5279 | 0.1924 | 0.1584 | 0.0332* | |
H42 | 0.4554 | 0.2040 | 0.3377 | 0.0279* | |
H43 | 0.4417 | 0.2891 | 0.3822 | 0.0279* | |
H44 | 0.5680 | 0.3020 | 0.4029 | 0.0279* | |
H45 | 0.6693 | 0.5721 | 0.3956 | 0.0399* | |
H46 | 0.5727 | 0.4813 | 0.4208 | 0.0399* | |
H47 | 0.5400 | 0.5555 | 0.3636 | 0.0399* | |
H48 | 0.0772 | 0.0464 | 0.1268 | 0.0283* | |
H49 | 0.1334 | 0.1252 | 0.2141 | 0.0283* | |
H50 | 0.2109 | 0.0894 | 0.1867 | 0.0283* | |
H51 | 0.0693 | 0.2834 | 0.0317 | 0.0284* | |
H52 | 0.0582 | 0.2664 | 0.1221 | 0.0284* | |
H53 | −0.0091 | 0.1711 | 0.0452 | 0.0284* | |
H54 | 0.1730 | 0.2739 | −0.0633 | 0.0259* | |
H55 | 0.1498 | 0.1940 | −0.1978 | 0.0271* | |
H56 | 0.1885 | −0.0399 | −0.0823 | 0.0224* | |
H57 | 0.1984 | 0.0330 | 0.0483 | 0.0216* | |
H58 | 0.2069 | 0.1395 | −0.2966 | 0.0211* | |
H59 | 0.0378 | −0.2220 | −0.3468 | 0.0362* | |
H60 | 0.0637 | −0.1383 | −0.2155 | 0.0271* | |
H61 | 0.2690 | 0.2885 | −0.5036 | 0.0419* | |
H62 | 0.2221 | 0.1986 | −0.6404 | 0.0317* | |
H63 | 0.1358 | 0.0145 | −0.6636 | 0.0304* | |
H64 | 0.0996 | −0.0728 | −0.5482 | 0.0287* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir(1) | 0.0192 (2) | 0.0164 (2) | 0.0161 (2) | 0.0117 (2) | 0.0047 (2) | 0.0028 (2) |
Ir(2) | 0.0193 (2) | 0.0148 (2) | 0.0170 (2) | 0.0102 (2) | 0.0046 (2) | 0.0023 (2) |
Cl(1) | 0.028 (1) | 0.022 (1) | 0.020 (1) | 0.015 (1) | 0.005 (1) | 0.007 (1) |
Cl(2) | 0.033 (1) | 0.026 (1) | 0.030 (1) | 0.021 (1) | 0.013 (1) | 0.004 (1) |
Cl(3) | 0.031 (1) | 0.028 (1) | 0.022 (1) | 0.017 (1) | 0.008 (1) | 0.000 (1) |
Cl(4) | 0.030 (1) | 0.021 (1) | 0.028 (1) | 0.016 (1) | 0.007 (1) | 0.010 (1) |
P(1) | 0.022 (1) | 0.024 (1) | 0.016 (1) | 0.014 (1) | 0.006 (1) | 0.005 (1) |
P(2) | 0.020 (1) | 0.023 (1) | 0.014 (1) | 0.014 (1) | 0.003 (1) | 0.004 (1) |
N(1) | 0.024 (5) | 0.025 (5) | 0.027 (5) | 0.008 (4) | 0.009 (4) | 0.004 (4) |
N(2) | 0.045 (6) | 0.021 (5) | 0.037 (5) | 0.021 (5) | 0.024 (5) | 0.011 (4) |
N(3) | 0.035 (5) | 0.032 (5) | 0.018 (4) | 0.018 (5) | 0.013 (4) | 0.004 (4) |
N(4) | 0.037 (5) | 0.030 (5) | 0.012 (4) | 0.014 (4) | 0.008 (4) | 0.003 (4) |
C(1) | 0.015 (5) | 0.015 (5) | 0.033 (6) | 0.008 (4) | 0.006 (4) | 0.003 (5) |
C(2) | 0.030 (6) | 0.034 (6) | 0.014 (5) | 0.022 (5) | 0.007 (4) | 0.003 (5) |
C(3) | 0.018 (5) | 0.023 (6) | 0.026 (5) | 0.016 (5) | 0.000 (4) | 0.003 (5) |
C(4) | 0.020 (5) | 0.010 (5) | 0.027 (5) | 0.012 (4) | 0.007 (4) | 0.004 (4) |
C(5) | 0.011 (5) | 0.018 (5) | 0.028 (6) | 0.012 (4) | 0.001 (4) | 0.001 (5) |
C(6) | 0.049 (7) | 0.024 (6) | 0.028 (6) | 0.024 (6) | 0.003 (5) | −0.005 (5) |
C(7) | 0.032 (6) | 0.053 (8) | 0.024 (6) | 0.028 (6) | 0.005 (5) | 0.004 (5) |
C(8) | 0.035 (6) | 0.027 (6) | 0.032 (6) | 0.020 (5) | 0.005 (5) | 0.001 (5) |
C(9) | 0.030 (6) | 0.027 (6) | 0.028 (6) | 0.020 (5) | 0.012 (5) | 0.006 (5) |
C(10) | 0.032 (6) | 0.021 (6) | 0.039 (6) | 0.008 (5) | 0.025 (5) | 0.013 (5) |
C(11) | 0.032 (6) | 0.021 (6) | 0.022 (5) | 0.011 (5) | 0.006 (5) | 0.003 (5) |
C(12) | 0.029 (6) | 0.036 (7) | 0.043 (7) | 0.023 (6) | 0.013 (5) | 0.015 (5) |
C(13) | 0.019 (5) | 0.019 (5) | 0.018 (5) | 0.011 (4) | 0.005 (4) | 0.003 (4) |
C(14) | 0.040 (6) | 0.021 (6) | 0.024 (5) | 0.017 (5) | 0.017 (5) | 0.011 (5) |
C(15) | 0.039 (7) | 0.022 (6) | 0.032 (6) | 0.017 (5) | 0.019 (5) | 0.012 (5) |
C(16) | 0.020 (5) | 0.030 (6) | 0.025 (6) | 0.018 (5) | 0.009 (4) | 0.005 (5) |
C(17) | 0.037 (6) | 0.025 (6) | 0.020 (5) | 0.012 (5) | 0.013 (5) | 0.003 (5) |
C(18) | 0.042 (7) | 0.021 (6) | 0.032 (6) | 0.015 (5) | 0.015 (5) | 0.004 (5) |
C(19) | 0.011 (5) | 0.031 (6) | 0.016 (5) | 0.006 (5) | 0.003 (4) | 0.005 (5) |
C(20) | 0.030 (6) | 0.035 (7) | 0.019 (5) | 0.011 (5) | 0.011 (5) | 0.006 (5) |
C(21) | 0.034 (6) | 0.012 (5) | 0.027 (6) | 0.000 (5) | 0.010 (5) | 0.005 (5) |
C(22) | 0.013 (5) | 0.032 (7) | 0.019 (5) | 0.005 (5) | 0.007 (4) | 0.003 (5) |
C(23) | 0.023 (6) | 0.022 (6) | 0.031 (6) | 0.014 (5) | 0.014 (5) | 0.014 (5) |
C(24) | 0.016 (5) | 0.016 (5) | 0.018 (5) | 0.005 (4) | 0.003 (4) | 0.007 (4) |
C(25) | 0.034 (6) | 0.030 (6) | 0.022 (6) | 0.018 (5) | 0.005 (5) | 0.016 (5) |
C(26) | 0.035 (6) | 0.034 (7) | 0.022 (6) | 0.018 (6) | 0.012 (5) | 0.011 (5) |
C(27) | 0.031 (6) | 0.024 (6) | 0.023 (6) | 0.006 (5) | 0.013 (5) | 0.002 (5) |
C(28) | 0.057 (8) | 0.039 (7) | 0.030 (6) | 0.020 (6) | 0.026 (6) | 0.009 (6) |
C(29) | 0.017 (5) | 0.014 (5) | 0.032 (6) | 0.008 (4) | 0.003 (4) | 0.004 (5) |
C(30) | 0.027 (6) | 0.023 (6) | 0.025 (6) | 0.015 (5) | 0.008 (5) | 0.000 (5) |
C(31) | 0.010 (5) | 0.019 (5) | 0.021 (5) | 0.006 (4) | 0.002 (4) | −0.002 (4) |
C(32) | 0.021 (5) | 0.025 (6) | 0.019 (5) | 0.013 (5) | −0.001 (4) | −0.002 (5) |
C(33) | 0.016 (5) | 0.024 (6) | 0.029 (6) | 0.011 (5) | −0.005 (4) | −0.002 (5) |
C(34) | 0.025 (6) | 0.024 (6) | 0.037 (6) | 0.008 (5) | 0.011 (5) | 0.013 (5) |
C(35) | 0.037 (7) | 0.030 (7) | 0.035 (6) | 0.012 (6) | 0.018 (5) | 0.000 (5) |
C(36) | 0.022 (5) | 0.026 (6) | 0.038 (6) | 0.019 (5) | 0.005 (5) | 0.004 (5) |
C(37) | 0.024 (6) | 0.024 (6) | 0.016 (5) | 0.008 (5) | 0.003 (4) | 0.002 (4) |
C(38) | 0.033 (6) | 0.028 (6) | 0.028 (6) | 0.015 (5) | −0.005 (5) | −0.005 (5) |
C(39) | 0.023 (5) | 0.029 (6) | 0.010 (5) | 0.009 (5) | 0.007 (4) | 0.006 (4) |
C(40) | 0.021 (5) | 0.032 (6) | 0.014 (5) | 0.014 (5) | 0.003 (4) | −0.002 (4) |
C(41) | 0.012 (5) | 0.019 (5) | 0.020 (5) | 0.007 (4) | 0.004 (4) | −0.001 (4) |
C(42) | 0.022 (5) | 0.010 (5) | 0.028 (6) | 0.004 (4) | 0.011 (5) | 0.006 (4) |
C(43) | 0.023 (5) | 0.027 (6) | 0.016 (5) | 0.012 (5) | 0.007 (4) | 0.004 (4) |
C(44) | 0.013 (5) | 0.023 (6) | 0.012 (5) | 0.008 (4) | 0.007 (4) | −0.002 (4) |
C(45) | 0.023 (5) | 0.017 (5) | 0.020 (5) | 0.014 (5) | 0.010 (4) | 0.007 (4) |
C(46) | 0.018 (5) | 0.018 (5) | 0.018 (5) | 0.010 (4) | 0.005 (4) | 0.005 (4) |
C(47) | 0.015 (5) | 0.037 (6) | 0.010 (5) | 0.015 (5) | 0.005 (4) | 0.001 (4) |
C(48) | 0.021 (5) | 0.017 (5) | 0.017 (5) | 0.011 (5) | 0.002 (4) | 0.004 (4) |
C(49) | 0.024 (6) | 0.042 (7) | 0.011 (5) | 0.020 (5) | 0.003 (4) | 0.008 (5) |
C(50) | 0.033 (6) | 0.021 (6) | 0.027 (6) | 0.008 (5) | 0.006 (5) | 0.001 (5) |
C(51) | 0.026 (6) | 0.029 (6) | 0.012 (5) | 0.016 (5) | 0.002 (4) | 0.002 (4) |
C(52) | 0.020 (5) | 0.024 (6) | 0.023 (5) | 0.012 (5) | 0.006 (4) | 0.005 (5) |
C(53) | 0.036 (7) | 0.037 (7) | 0.025 (6) | 0.017 (6) | 0.004 (5) | 0.007 (5) |
C(54) | 0.033 (6) | 0.042 (7) | 0.018 (5) | 0.018 (6) | 0.010 (5) | 0.006 (5) |
C(55) | 0.031 (6) | 0.033 (7) | 0.017 (5) | 0.022 (5) | 0.006 (5) | 0.006 (5) |
C(56) | 0.022 (5) | 0.031 (6) | 0.019 (5) | 0.019 (5) | 0.004 (4) | 0.004 (5) |
IR1—CL1 | 2.423 (2) | C49—C52 | 1.47 (1) |
IR1—CL2 | 2.410 (2) | C50—C51 | 1.39 (1) |
IR1—P1 | 2.285 (3) | C52—C56 | 1.40 (1) |
IR1—C1 | 2.247 (9) | C53—C54 | 1.40 (1) |
IR1—C2 | 2.139 (9) | C54—C55 | 1.38 (1) |
IR1—C3 | 2.167 (9) | C55—C56 | 1.38 (1) |
IR1—C4 | 2.141 (9) | C6—H1 | 0.9500 |
IR1—C5 | 2.231 (9) | C6—H2 | 0.9500 |
IR2—CL3 | 2.412 (2) | C6—H3 | 0.9500 |
IR2—CL4 | 2.418 (2) | C7—H4 | 0.9500 |
IR2—P2 | 2.285 (2) | C7—H5 | 0.9500 |
IR2—C29 | 2.224 (9) | C7—H6 | 0.9500 |
IR2—C30 | 2.131 (10) | C8—H7 | 0.9500 |
IR2—C31 | 2.165 (9) | C8—H8 | 0.9500 |
IR2—C32 | 2.158 (9) | C8—H9 | 0.9500 |
IR2—C33 | 2.251 (9) | C9—H10 | 0.9500 |
P1—C11 | 1.821 (10) | C9—H11 | 0.9500 |
P1—C12 | 1.81 (1) | C9—H12 | 0.9500 |
P1—C13 | 1.827 (10) | C10—H13 | 0.9500 |
P2—C39 | 1.824 (10) | C10—H14 | 0.9500 |
P2—C40 | 1.813 (10) | C10—H15 | 0.9500 |
P2—C41 | 1.817 (9) | C11—H16 | 0.9500 |
N1—C21 | 1.35 (1) | C11—H17 | 0.9500 |
N1—C22 | 1.35 (1) | C11—H18 | 0.9500 |
N2—C24 | 1.34 (1) | C12—H19 | 0.9500 |
N2—C28 | 1.36 (1) | C12—H20 | 0.9500 |
N3—C49 | 1.36 (1) | C12—H21 | 0.9500 |
N3—C50 | 1.32 (1) | C14—H22 | 0.9500 |
N4—C52 | 1.35 (1) | C15—H23 | 0.9500 |
N4—C53 | 1.34 (1) | C17—H24 | 0.9500 |
C1—C2 | 1.46 (1) | C18—H25 | 0.9500 |
C1—C5 | 1.40 (1) | C20—H26 | 0.9500 |
C1—C6 | 1.49 (1) | C21—H27 | 0.9500 |
C2—C3 | 1.47 (1) | C23—H28 | 0.9500 |
C2—C7 | 1.49 (1) | C25—H29 | 0.9500 |
C3—C4 | 1.41 (1) | C26—H30 | 0.9500 |
C3—C8 | 1.46 (1) | C27—H31 | 0.9500 |
C4—C5 | 1.45 (1) | C28—H32 | 0.9500 |
C4—C9 | 1.50 (1) | C34—H33 | 0.9500 |
C5—C10 | 1.50 (1) | C34—H34 | 0.9500 |
C13—C14 | 1.38 (1) | C34—H35 | 0.9500 |
C13—C18 | 1.39 (1) | C35—H36 | 0.9500 |
C14—C15 | 1.39 (1) | C35—H37 | 0.9500 |
C15—C16 | 1.39 (1) | C35—H38 | 0.9500 |
C16—C17 | 1.37 (1) | C36—H39 | 0.9500 |
C16—C19 | 1.50 (1) | C36—H40 | 0.9500 |
C17—C18 | 1.39 (1) | C36—H41 | 0.9500 |
C19—C20 | 1.40 (1) | C37—H42 | 0.9500 |
C19—C23 | 1.41 (1) | C37—H43 | 0.9500 |
C20—C21 | 1.38 (1) | C37—H44 | 0.9500 |
C22—C23 | 1.38 (1) | C38—H45 | 0.9500 |
C22—C24 | 1.49 (1) | C38—H46 | 0.9500 |
C24—C25 | 1.38 (1) | C38—H47 | 0.9500 |
C25—C26 | 1.39 (1) | C39—H48 | 0.9500 |
C26—C27 | 1.35 (1) | C39—H49 | 0.9500 |
C27—C28 | 1.38 (1) | C39—H50 | 0.9500 |
C29—C30 | 1.45 (1) | C40—H51 | 0.9500 |
C29—C33 | 1.41 (1) | C40—H52 | 0.9500 |
C29—C34 | 1.52 (1) | C40—H53 | 0.9500 |
C30—C31 | 1.40 (1) | C42—H54 | 0.9500 |
C30—C35 | 1.53 (1) | C43—H55 | 0.9500 |
C31—C32 | 1.45 (1) | C45—H56 | 0.9500 |
C31—C36 | 1.49 (1) | C46—H57 | 0.9500 |
C32—C33 | 1.46 (1) | C48—H58 | 0.9500 |
C32—C37 | 1.48 (1) | C50—H59 | 0.9500 |
C33—C38 | 1.49 (1) | C51—H60 | 0.9500 |
C41—C42 | 1.40 (1) | C53—H61 | 0.9500 |
C47—C48 | 1.39 (1) | C54—H62 | 0.9500 |
C47—C51 | 1.40 (1) | C55—H63 | 0.9500 |
C48—C49 | 1.40 (1) | C56—H64 | 0.9500 |
CL1—IR1—CL2 | 89.98 (8) | C3—C8—H7 | 109.4738 |
CL1—IR1—P1 | 85.58 (8) | C3—C8—H8 | 109.4734 |
CL2—IR1—P1 | 88.71 (9) | C3—C8—H9 | 109.4721 |
CL3—IR2—CL4 | 90.05 (9) | H7—C8—H8 | 109.4698 |
CL3—IR2—P2 | 86.38 (9) | H7—C8—H9 | 109.4687 |
CL4—IR2—P2 | 87.45 (8) | H8—C8—H9 | 109.4695 |
IR1—P1—C11 | 113.5 (3) | C4—C9—H10 | 109.4745 |
IR1—P1—C12 | 114.6 (4) | C4—C9—H11 | 109.4719 |
IR1—P1—C13 | 115.8 (3) | C4—C9—H12 | 109.4735 |
C11—P1—C12 | 103.2 (5) | H10—C9—H11 | 109.4697 |
C11—P1—C13 | 105.4 (4) | H10—C9—H12 | 109.4713 |
C12—P1—C13 | 102.9 (5) | H11—C9—H12 | 109.4665 |
IR2—P2—C39 | 114.4 (3) | C5—C10—H13 | 109.4669 |
IR2—P2—C40 | 114.8 (3) | C5—C10—H14 | 109.4694 |
IR2—P2—C41 | 115.3 (3) | C5—C10—H15 | 109.4664 |
C39—P2—C40 | 103.6 (5) | H13—C10—H14 | 109.4761 |
C39—P2—C41 | 104.0 (4) | H13—C10—H15 | 109.4736 |
C40—P2—C41 | 103.3 (4) | H14—C10—H15 | 109.4749 |
C21—N1—C22 | 115.7 (9) | P1—C11—H16 | 109.4705 |
C24—N2—C28 | 115.9 (9) | P1—C11—H17 | 109.4704 |
C49—N3—C50 | 117.2 (8) | P1—C11—H18 | 109.4717 |
C52—N4—C53 | 115.8 (9) | H16—C11—H17 | 109.4709 |
C2—C1—C5 | 107.5 (8) | H16—C11—H18 | 109.4712 |
C2—C1—C6 | 123.4 (9) | H17—C11—H18 | 109.4726 |
C5—C1—C6 | 129.1 (9) | P1—C12—H19 | 109.4729 |
C1—C2—C3 | 107.3 (8) | P1—C12—H20 | 109.4716 |
C1—C2—C7 | 125.5 (9) | P1—C12—H21 | 109.4735 |
C3—C2—C7 | 126.7 (9) | H19—C12—H20 | 109.4689 |
C2—C3—C4 | 106.8 (8) | H19—C12—H21 | 109.4715 |
C2—C3—C8 | 124.2 (9) | H20—C12—H21 | 109.4690 |
C4—C3—C8 | 128.6 (9) | C13—C14—H22 | 120.0631 |
C3—C4—C5 | 108.7 (8) | C15—C14—H22 | 120.0657 |
C3—C4—C9 | 126.2 (9) | C14—C15—H23 | 119.1267 |
C5—C4—C9 | 124.2 (9) | C16—C15—H23 | 119.1317 |
C1—C5—C4 | 109.3 (9) | C16—C17—H24 | 119.3656 |
C1—C5—C10 | 127.1 (9) | C18—C17—H24 | 119.3661 |
C4—C5—C10 | 123.5 (8) | C13—C18—H25 | 119.6818 |
P1—C13—C14 | 122.3 (7) | C17—C18—H25 | 119.6828 |
P1—C13—C18 | 118.9 (8) | C19—C20—H26 | 120.7834 |
C14—C13—C18 | 118.8 (9) | C21—C20—H26 | 120.7803 |
C13—C14—C15 | 119.9 (9) | N1—C21—H27 | 117.3910 |
C14—C15—C16 | 121.7 (10) | C20—C21—H27 | 117.3979 |
C15—C16—C17 | 117.7 (9) | C19—C23—H28 | 120.4649 |
C15—C16—C19 | 121.1 (10) | C22—C23—H28 | 120.4662 |
C17—C16—C19 | 121.2 (9) | C24—C25—H29 | 120.3488 |
C16—C17—C18 | 121.3 (9) | C26—C25—H29 | 120.3575 |
C13—C18—C17 | 120.6 (10) | C25—C26—H30 | 120.3415 |
C16—C19—C20 | 121.5 (9) | C27—C26—H30 | 120.3395 |
C16—C19—C23 | 121.1 (9) | C26—C27—H31 | 120.9388 |
C20—C19—C23 | 117.4 (9) | C28—C27—H31 | 120.9394 |
C19—C20—C21 | 118.4 (9) | N2—C28—H32 | 117.6701 |
N1—C21—C20 | 125.2 (10) | C27—C28—H32 | 117.6650 |
N1—C22—C23 | 124.1 (9) | C29—C34—H33 | 109.4729 |
N1—C22—C24 | 115.9 (9) | C29—C34—H34 | 109.4719 |
C23—C22—C24 | 120.0 (10) | C29—C34—H35 | 109.4726 |
C19—C23—C22 | 119.1 (10) | H33—C34—H34 | 109.4706 |
N2—C24—C22 | 115.4 (9) | H33—C34—H35 | 109.4700 |
N2—C24—C25 | 122.7 (10) | H34—C34—H35 | 109.4693 |
C22—C24—C25 | 121.9 (10) | C30—C35—H36 | 109.4751 |
C24—C25—C26 | 119 (1) | C30—C35—H37 | 109.4767 |
C25—C26—C27 | 119.3 (10) | C30—C35—H38 | 109.4779 |
C26—C27—C28 | 118 (1) | H36—C35—H37 | 109.4646 |
N2—C28—C27 | 124 (1) | H36—C35—H38 | 109.4674 |
C30—C29—C33 | 108.8 (9) | H37—C35—H38 | 109.4657 |
C30—C29—C34 | 124.8 (9) | C31—C36—H39 | 109.4707 |
C33—C29—C34 | 126.4 (9) | C31—C36—H40 | 109.4709 |
C29—C30—C31 | 108.1 (8) | C31—C36—H41 | 109.4706 |
C29—C30—C35 | 125.6 (9) | H39—C36—H40 | 109.4715 |
C31—C30—C35 | 125.8 (9) | H39—C36—H41 | 109.4727 |
C30—C31—C32 | 108.3 (8) | H40—C36—H41 | 109.4709 |
C30—C31—C36 | 126.7 (9) | C32—C37—H42 | 109.4691 |
C32—C31—C36 | 124.5 (9) | C32—C37—H43 | 109.4697 |
C31—C32—C33 | 107.1 (9) | C32—C37—H44 | 109.4669 |
C31—C32—C37 | 128.8 (9) | H42—C37—H43 | 109.4750 |
C33—C32—C37 | 123.1 (9) | H42—C37—H44 | 109.4723 |
C29—C33—C32 | 107.2 (9) | H43—C37—H44 | 109.4744 |
C29—C33—C38 | 127.5 (10) | C33—C38—H45 | 109.4708 |
C32—C33—C38 | 125.3 (10) | C33—C38—H46 | 109.4743 |
P2—C41—C42 | 120.4 (7) | C33—C38—H47 | 109.4747 |
P2—C41—C46 | 121.2 (7) | H45—C38—H46 | 109.4671 |
C42—C41—C46 | 118.4 (8) | H45—C38—H47 | 109.4680 |
C41—C42—C43 | 120.3 (9) | H46—C38—H47 | 109.4724 |
C42—C43—C44 | 120.3 (9) | P2—C39—H48 | 109.4700 |
C43—C44—C45 | 119.4 (8) | P2—C39—H49 | 109.4681 |
C43—C44—C47 | 121.4 (9) | P2—C39—H50 | 109.4701 |
C45—C44—C47 | 119.2 (9) | H48—C39—H49 | 109.4718 |
C44—C45—C46 | 120.1 (9) | H48—C39—H50 | 109.4748 |
C41—C46—C45 | 121.2 (9) | H49—C39—H50 | 109.4726 |
C44—C47—C48 | 122.7 (9) | P2—C40—H51 | 109.4691 |
C44—C47—C51 | 120.3 (9) | P2—C40—H52 | 109.4697 |
C48—C47—C51 | 116.9 (8) | P2—C40—H53 | 109.4694 |
C47—C48—C49 | 120.2 (9) | H51—C40—H52 | 109.4732 |
N3—C49—C48 | 122.0 (9) | H51—C40—H53 | 109.4724 |
N3—C49—C52 | 116.4 (9) | H52—C40—H53 | 109.4734 |
C48—C49—C52 | 121.6 (10) | C41—C42—H54 | 119.8409 |
N3—C50—C51 | 124.4 (10) | C43—C42—H54 | 119.8460 |
C47—C51—C50 | 119.1 (9) | C42—C43—H55 | 119.8286 |
N4—C52—C49 | 116.4 (9) | C44—C43—H55 | 119.8251 |
N4—C52—C56 | 123.3 (9) | C44—C45—H56 | 119.9704 |
C49—C52—C56 | 120.2 (10) | C46—C45—H56 | 119.9662 |
N4—C53—C54 | 124 (1) | C41—C46—H57 | 119.3860 |
C53—C54—C55 | 118.2 (10) | C45—C46—H57 | 119.3884 |
C54—C55—C56 | 118.8 (9) | C47—C48—H58 | 119.9178 |
C52—C56—C55 | 119.2 (10) | C49—C48—H58 | 119.9194 |
C1—C6—H1 | 109.4727 | N3—C50—H59 | 117.7825 |
C1—C6—H2 | 109.4737 | C51—C50—H59 | 117.7836 |
C1—C6—H3 | 109.4732 | C47—C51—H60 | 120.4467 |
H1—C6—H2 | 109.4684 | C50—C51—H60 | 120.4497 |
H1—C6—H3 | 109.4696 | N4—C53—H61 | 117.6937 |
H2—C6—H3 | 109.4697 | C54—C53—H61 | 117.6895 |
C2—C7—H4 | 109.4716 | C53—C54—H62 | 120.8919 |
C2—C7—H5 | 109.4742 | C55—C54—H62 | 120.8927 |
C2—C7—H6 | 109.4725 | C54—C55—H63 | 120.5786 |
H4—C7—H5 | 109.4683 | C56—C55—H63 | 120.5791 |
H4—C7—H6 | 109.4684 | C52—C56—H64 | 120.3925 |
H5—C7—H6 | 109.4724 | C55—C56—H64 | 120.3937 |
Experimental details
Crystal data | |
Chemical formula | [Ir(C10H15)(C18H17N2P)Cl2] |
Mr | 690.67 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 123 |
a, b, c (Å) | 13.592 (4), 14.545 (4), 16.427 (4) |
α, β, γ (°) | 90.018 (4), 109.683 (4), 117.455 (4) |
V (Å3) | 2666 (1) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 5.30 |
Crystal size (mm) | 0.17 × 0.09 × 0.08 |
Data collection | |
Diffractometer | SMART CCD diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.314, 0.654 |
No. of measured, independent and observed [I > 3.00σ(I)] reflections | 13236, 8337, 5843 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.590 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.046, 1.23 |
No. of reflections | 5843 |
No. of parameters | 613 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.16, −2.33 |
Computer programs: SMART (Bruker, 1995-1999), SAINT (Bruker, 2002), SAINT, SIR92 (Altomare, 1993), TEXSAN (Molecular Structure Corporation, 1985, 1992), please provide, TEXSAN.
IR1—CL1 | 2.423 (2) | IR2—CL3 | 2.412 (2) |
IR1—CL2 | 2.410 (2) | IR2—CL4 | 2.418 (2) |
IR1—P1 | 2.285 (3) | IR2—P2 | 2.285 (2) |
IR1—C1 | 2.247 (9) | IR2—C29 | 2.224 (9) |
IR1—C2 | 2.139 (9) | IR2—C30 | 2.131 (10) |
IR1—C3 | 2.167 (9) | IR2—C31 | 2.165 (9) |
IR1—C4 | 2.141 (9) | IR2—C32 | 2.158 (9) |
IR1—C5 | 2.231 (9) | IR2—C33 | 2.251 (9) |
CL1—IR1—CL2 | 89.98 (8) | C11—P1—C12 | 103.2 (5) |
CL1—IR1—P1 | 85.58 (8) | C11—P1—C13 | 105.4 (4) |
CL2—IR1—P1 | 88.71 (9) | C12—P1—C13 | 102.9 (5) |
CL3—IR2—CL4 | 90.05 (9) | IR2—P2—C39 | 114.4 (3) |
CL3—IR2—P2 | 86.38 (9) | IR2—P2—C40 | 114.8 (3) |
CL4—IR2—P2 | 87.45 (8) | IR2—P2—C41 | 115.3 (3) |
IR1—P1—C11 | 113.5 (3) | C39—P2—C40 | 103.6 (5) |
IR1—P1—C12 | 114.6 (4) | C39—P2—C41 | 104.0 (4) |
IR1—P1—C13 | 115.8 (3) | C40—P2—C41 | 103.3 (4) |
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One form of C—H bond activation involves photochemically induced reductive elimination of molecular hydrogen from an Ir—Cp* dihydride complex (Janowicz & Bergman, 1983). The resulting electron-deficient species is able to oxidatively add hydrocarbons. Unfortunately, the photochemical reaction has a low quantum yield and also requires high energy photons.
Therefore, it would be advantageous to attach a chromophore to an Ir—Cp* dihydride. Efficient energy transfer from the chromophore would activate the Ir—Cp* center. The title compound, (I), possesses a bipyridine-functionalized linker intended to subsequently bind a rhenium chromophore. Transformation of the resulting dichloride into an Ir—Cp* dihydride may generate a complex with new and improved photochemical C—H bond activation.
This compound crystallized as orange parallelepipeds, following vapor diffusion of ether into a methylene chloride solution. The crystal structure confirmed that the molecule is an Ir(III) center coordinated in piano-stool fashion by an η5-Cp* ligand, two chlorides and a dimethyl aryl phosphine ligand. The aromatic arm of the phosphine is a p-phenyl-2,2'-bipyridine connected through the 5 position of the pyridine, giving the ligand an overall boomerang shape. There are two molecules of the complex in the asymmetric unit (Fig. 1). The molecules differ primarily in the conformation of the conjugated moiety. In one molecule, the three rings are close to coplanar; the proximal (C19–23, N1) and terminal (C24–28, N2) rings of the bipyridine form angles of 8.4° and 5.5° to the phenyl (C13–18) and 10.6° with each other. The three conjugated rings that comprise the moeity on the other molecule are twisted with respect to one another, with interplanar angles of 28.0° and 27.1° for the proximal (C47–51, N3) and terminal (C52–56, N4) rings to the phenyl ring (C41–46). The bipyridine in this second molecule is closer to planar than in the first, with an interplanar angle of 5.6°.