03551
Crystal Structure Report for 03551
A clear intense yellow-orange, plate-like specimen of C15H17Cl2NRu, approximate dimensions 0.055 mm x 0.160 mm x 0.223 mm, was used for the X-ray crystallographic analysis.
The X-ray intensity data were measured (λ = 0.71073 Å).
The total exposure time was 0.52 hours.
The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data using a monoclinic unit cell yielded a total of 28996 reflections to a maximum θ angle of 25.35° (0.83 Å resolution), of which 2686 were independent (average redundancy 10.795, completeness = 99.8%, Rint = 6.32%, Rsig = 3.23%) and 2176 (81.01%) were greater than 2σ(F2).
The final cell constants of a = 10.0271(5) Å, b = 9.9616(5) Å, c = 15.4734(6) Å, β = 107.260(2)°, volume = 1475.98(12) Å3, are based upon the refinement of the XYZ-centroids of 4059 reflections above 20 σ(I) with 5.881° < 2θ < 47.23°.
Data were corrected for absorption effects using the Multi-Scan method (SADABS). The ratio of minimum to maximum apparent transmission was 0.878. The calculated minimum and maximum transmission coefficients (based on crystal size) are 0.7440 and 0.9270.
The structure was solved and refined using the Bruker SHELXTL Software Package, using the space group P 1 21/c 1, with Z = 4 for the formula unit, C15H17Cl2NRu.
The final anisotropic full-matrix least-squares refinement on F2 with 180 variables converged at R1 = 2.59%, for the observed data and wR2 = 6.14% for all data. The goodness-of-fit was 1.062. The largest peak in the final difference electron density synthesis was 0.426 e-/Å3 and the largest hole was -0.523 e-/Å3 with an RMS deviation of 0.123 e-/Å3. On the basis of the final model, the calculated density was 1.725 g/cm3 and F(000), 768 e-.
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Table 1. Sample and crystal data for 03551.
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| Identification code | 03551 |
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| Chemical formula | C15H17Cl2NRu |
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| Formula weight | 383.27 g/mol |
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| Temperature | 150(2) K |
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| Wavelength | 0.71073 Å |
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| Crystal size | 0.055 x 0.160 x 0.223 mm |
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| Crystal habit | clear intense yellow-orange plate |
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| Crystal system | monoclinic |
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| Space group | P 1 21/c 1 |
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| Unit cell dimensions | a = 10.0271(5) Å | α = 90° |
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| b = 9.9616(5) Å | β = 107.260(2)° |
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| c = 15.4734(6) Å | γ = 90° |
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| Volume | 1475.98(12) Å3 |
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| Z | 4 |
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| Density (calculated) | 1.725 g/cm3 |
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| Absorption coefficient | 1.409 mm-1 |
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| F(000) | 768 |
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Table 2. Data collection and structure refinement for 03551.
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| Theta range for data collection | 3.43 to 25.35° |
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| Index ranges | -12<=h<=12, -12<=k<=11, -18<=l<=18 |
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| Reflections collected | 28996 |
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| Independent reflections | 2686 [R(int) = 0.0632] |
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| Coverage of independent reflections | 99.8% |
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| Absorption correction | Multi-Scan |
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| Max. and min. transmission | 0.9270 and 0.7440 |
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| Structure solution technique | direct methods |
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| Structure solution program | XT, VERSION 2018/2 |
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| Refinement method | Full-matrix least-squares on F2 |
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| Refinement program | SHELXL-2019/1 (Sheldrick, 2019) |
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| Function minimized | Σ w(Fo2 - Fc2)2 |
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| Data / restraints / parameters | 2686 / 0 / 180 |
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| Goodness-of-fit on F2 | 1.062 |
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| Δ/σmax | 0.001 |
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| Final R indices | 2176 data; I>2σ(I) | R1 = 0.0259, wR2 = 0.0576 |
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| all data | R1 = 0.0362, wR2 = 0.0614 |
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| Weighting scheme | w=1/[σ2(Fo2)+(0.0233P)2+1.1976P]
where P=(Fo2+2Fc2)/3 |
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| Largest diff. peak and hole | 0.426 and -0.523 eÅ-3 |
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| R.M.S. deviation from mean | 0.123 eÅ-3 |
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Table 3. Atomic coordinates and equivalent isotropic atomic
displacement parameters (Å2) for 03551.
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U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
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| x/a | y/b | z/c | U(eq) |
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| C1 | 0.8151(3) | 0.5531(3) | 0.3441(2) | 0.0155(6) |
| C2 | 0.7795(3) | 0.4305(3) | 0.2961(2) | 0.0174(7) |
| C3 | 0.6516(3) | 0.4205(3) | 0.2250(2) | 0.0189(7) |
| C4 | 0.5627(3) | 0.5327(3) | 0.2021(2) | 0.0191(7) |
| C5 | 0.5969(3) | 0.6564(3) | 0.24837(18) | 0.0162(7) |
| C6 | 0.7202(3) | 0.6638(3) | 0.32376(19) | 0.0145(6) |
| C7 | 0.7350(3) | 0.7734(3) | 0.39227(19) | 0.0145(6) |
| C8 | 0.8042(3) | 0.8936(3) | 0.3922(2) | 0.0171(7) |
| C9 | 0.8088(3) | 0.9894(3) | 0.4576(2) | 0.0205(7) |
| C10 | 0.7422(3) | 0.9662(3) | 0.5233(2) | 0.0222(7) |
| C11 | 0.6749(3) | 0.8451(3) | 0.5248(2) | 0.0196(7) |
| C12 | 0.6721(3) | 0.7498(3) | 0.45980(19) | 0.0154(7) |
| C13 | 0.8720(3) | 0.3077(3) | 0.3199(2) | 0.0229(7) |
| C14 | 0.9826(3) | 0.3165(3) | 0.4124(2) | 0.0336(9) |
| C15 | 0.9399(5) | 0.2834(4) | 0.2448(3) | 0.0517(12) |
| Cl1 | 0.64588(8) | 0.31117(7) | 0.44916(5) | 0.01990(18) |
| Cl2 | 0.35920(7) | 0.48150(8) | 0.32777(5) | 0.02093(19) |
| N1 | 0.6055(3) | 0.6187(3) | 0.46034(18) | 0.0162(6) |
| Ru1 | 0.60618(2) | 0.49945(2) | 0.34695(2) | 0.01222(9) |
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Table 4. Bond lengths (Å) for 03551.
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| C1-C2 | 1.419(4) | C1-C6 | 1.430(4) |
| C1-Ru1 | 2.175(3) | C2-C3 | 1.424(4) |
| C2-C13 | 1.513(4) | C2-Ru1 | 2.219(3) |
| C3-C4 | 1.408(4) | C3-Ru1 | 2.213(3) |
| C4-C5 | 1.415(4) | C4-Ru1 | 2.178(3) |
| C5-C6 | 1.428(4) | C5-Ru1 | 2.167(3) |
| C6-C7 | 1.498(4) | C6-Ru1 | 2.088(3) |
| C7-C8 | 1.384(4) | C7-C12 | 1.392(4) |
| C8-C9 | 1.382(4) | C9-C10 | 1.391(4) |
| C10-C11 | 1.385(4) | C11-C12 | 1.377(4) |
| C12-N1 | 1.467(4) | C13-C15 | 1.530(4) |
| C13-C14 | 1.531(4) | Cl1-Ru1 | 2.4092(7) |
| Cl2-Ru1 | 2.4119(8) | N1-Ru1 | 2.121(3) |
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Table 5. Bond angles (°) for 03551.
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| C2-C1-C6 | 120.1(3) | C2-C1-Ru1 | 72.85(17) |
| C6-C1-Ru1 | 67.15(16) | C1-C2-C3 | 119.6(3) |
| C1-C2-C13 | 121.9(3) | C3-C2-C13 | 118.5(3) |
| C1-C2-Ru1 | 69.47(16) | C3-C2-Ru1 | 71.03(17) |
| C13-C2-Ru1 | 130.7(2) | C4-C3-C2 | 119.8(3) |
| C4-C3-Ru1 | 69.95(17) | C2-C3-Ru1 | 71.49(16) |
| C3-C4-C5 | 121.6(3) | C3-C4-Ru1 | 72.66(17) |
| C5-C4-Ru1 | 70.56(16) | C4-C5-C6 | 118.7(3) |
| C4-C5-Ru1 | 71.42(17) | C6-C5-Ru1 | 67.44(15) |
| C5-C6-C1 | 119.9(3) | C5-C6-C7 | 119.7(3) |
| C1-C6-C7 | 119.1(3) | C5-C6-Ru1 | 73.40(16) |
| C1-C6-Ru1 | 73.73(17) | C7-C6-Ru1 | 113.22(18) |
| C8-C7-C12 | 119.1(3) | C8-C7-C6 | 125.1(3) |
| C12-C7-C6 | 115.9(3) | C9-C8-C7 | 120.3(3) |
| C8-C9-C10 | 120.1(3) | C11-C10-C9 | 119.9(3) |
| C12-C11-C10 | 119.5(3) | C11-C12-C7 | 121.1(3) |
| C11-C12-N1 | 121.3(3) | C7-C12-N1 | 117.6(3) |
| C2-C13-C15 | 108.8(3) | C2-C13-C14 | 113.7(3) |
| C15-C13-C14 | 110.9(3) | C12-N1-Ru1 | 112.39(18) |
| C6-Ru1-N1 | 80.73(10) | C6-Ru1-C5 | 39.16(11) |
| N1-Ru1-C5 | 99.68(11) | C6-Ru1-C1 | 39.12(11) |
| N1-Ru1-C1 | 96.79(11) | C5-Ru1-C1 | 69.46(11) |
| C6-Ru1-C4 | 69.92(11) | N1-Ru1-C4 | 135.84(11) |
| C5-Ru1-C4 | 38.02(11) | C1-Ru1-C4 | 80.91(11) |
| C6-Ru1-C3 | 82.56(11) | N1-Ru1-C3 | 163.05(11) |
| C5-Ru1-C3 | 68.46(11) | C1-Ru1-C3 | 68.10(11) |
| C4-Ru1-C3 | 37.39(11) | C6-Ru1-C2 | 69.84(11) |
| N1-Ru1-C2 | 131.44(11) | C5-Ru1-C2 | 81.27(11) |
| C1-Ru1-C2 | 37.67(11) | C4-Ru1-C2 | 67.72(11) |
| C3-Ru1-C2 | 37.49(11) | C6-Ru1-Cl1 | 136.98(8) |
| N1-Ru1-Cl1 | 86.19(8) | C5-Ru1-Cl1 | 171.14(8) |
| C1-Ru1-Cl1 | 103.41(8) | C4-Ru1-Cl1 | 137.52(8) |
| C3-Ru1-Cl1 | 104.33(8) | C2-Ru1-Cl1 | 89.87(8) |
| C6-Ru1-Cl2 | 129.16(8) | N1-Ru1-Cl2 | 83.58(7) |
| C5-Ru1-Cl2 | 97.97(8) | C1-Ru1-Cl2 | 167.35(8) |
| C4-Ru1-Cl2 | 89.99(9) | C3-Ru1-Cl2 | 109.41(8) |
| C2-Ru1-Cl2 | 144.81(8) | Cl1-Ru1-Cl2 | 89.23(3) |
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Table 6. Torsion angles (°) for 03551.
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| C6-C1-C2-C3 | 2.7(4) | Ru1-C1-C2-C3 | 52.3(2) |
| C6-C1-C2-C13 | -175.6(3) | Ru1-C1-C2-C13 | -126.0(3) |
| C6-C1-C2-Ru1 | -49.6(2) | C1-C2-C3-C4 | 1.0(4) |
| C13-C2-C3-C4 | 179.3(3) | Ru1-C2-C3-C4 | 52.5(2) |
| C1-C2-C3-Ru1 | -51.6(2) | C13-C2-C3-Ru1 | 126.7(3) |
| C2-C3-C4-C5 | -0.2(4) | Ru1-C3-C4-C5 | 53.1(2) |
| C2-C3-C4-Ru1 | -53.2(2) | C3-C4-C5-C6 | -4.2(4) |
| Ru1-C4-C5-C6 | 49.8(2) | C3-C4-C5-Ru1 | -54.0(3) |
| C4-C5-C6-C1 | 7.8(4) | Ru1-C5-C6-C1 | 59.4(2) |
| C4-C5-C6-C7 | -159.3(3) | Ru1-C5-C6-C7 | -107.7(2) |
| C4-C5-C6-Ru1 | -51.7(2) | C2-C1-C6-C5 | -7.1(4) |
| Ru1-C1-C6-C5 | -59.3(2) | C2-C1-C6-C7 | 160.1(3) |
| Ru1-C1-C6-C7 | 107.9(2) | C2-C1-C6-Ru1 | 52.2(2) |
| C5-C6-C7-C8 | -95.8(3) | C1-C6-C7-C8 | 97.0(3) |
| Ru1-C6-C7-C8 | -179.3(2) | C5-C6-C7-C12 | 83.6(3) |
| C1-C6-C7-C12 | -83.6(3) | Ru1-C6-C7-C12 | 0.1(3) |
| C12-C7-C8-C9 | -1.0(4) | C6-C7-C8-C9 | 178.5(3) |
| C7-C8-C9-C10 | -0.8(5) | C8-C9-C10-C11 | 2.0(5) |
| C9-C10-C11-C12 | -1.4(5) | C10-C11-C12-C7 | -0.5(5) |
| C10-C11-C12-N1 | 178.2(3) | C8-C7-C12-C11 | 1.6(4) |
| C6-C7-C12-C11 | -177.8(3) | C8-C7-C12-N1 | -177.1(3) |
| C6-C7-C12-N1 | 3.4(4) | C1-C2-C13-C15 | -109.2(3) |
| C3-C2-C13-C15 | 72.5(4) | Ru1-C2-C13-C15 | 161.4(3) |
| C1-C2-C13-C14 | 14.9(4) | C3-C2-C13-C14 | -163.3(3) |
| Ru1-C2-C13-C14 | -74.5(4) | C11-C12-N1-Ru1 | 176.1(2) |
| C7-C12-N1-Ru1 | -5.2(3) | | |
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Table 7. Anisotropic atomic displacement parameters (Å2)
for 03551.
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The anisotropic atomic displacement factor exponent takes the form:
-2π2[ h2 a*2 U11 + ... + 2 h k a* b* U12 ]
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| U11 | U22 | U33 | U23 | U13 | U12 |
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| C1 | 0.0174(16) | 0.0181(16) | 0.0143(16) | 0.0015(12) | 0.0099(13) | 0.0008(13) |
| C2 | 0.0202(16) | 0.0200(17) | 0.0178(17) | 0.0039(13) | 0.0146(14) | 0.0021(14) |
| C3 | 0.0255(18) | 0.0162(17) | 0.0184(17) | -0.0004(13) | 0.0116(15) | -0.0033(14) |
| C4 | 0.0234(17) | 0.0237(19) | 0.0118(16) | 0.0025(13) | 0.0077(14) | -0.0013(14) |
| C5 | 0.0211(16) | 0.0191(17) | 0.0111(15) | 0.0046(12) | 0.0089(14) | 0.0007(13) |
| C6 | 0.0207(16) | 0.0122(16) | 0.0150(16) | 0.0021(12) | 0.0119(14) | -0.0023(13) |
| C7 | 0.0133(15) | 0.0142(16) | 0.0142(16) | -0.0006(12) | 0.0012(13) | 0.0027(12) |
| C8 | 0.0171(16) | 0.0167(17) | 0.0177(16) | 0.0036(13) | 0.0052(14) | 0.0013(13) |
| C9 | 0.0200(16) | 0.0142(16) | 0.0252(18) | 0.0024(13) | 0.0037(14) | -0.0014(14) |
| C10 | 0.0257(18) | 0.0181(18) | 0.0213(18) | -0.0045(13) | 0.0045(15) | -0.0004(14) |
| C11 | 0.0225(17) | 0.0197(17) | 0.0185(16) | 0.0004(13) | 0.0089(14) | 0.0016(14) |
| C12 | 0.0166(16) | 0.0146(16) | 0.0146(16) | 0.0009(12) | 0.0043(13) | 0.0006(13) |
| C13 | 0.0252(18) | 0.0197(18) | 0.0286(19) | 0.0015(14) | 0.0155(16) | 0.0062(15) |
| C14 | 0.0244(19) | 0.022(2) | 0.052(2) | 0.0063(17) | 0.0076(18) | 0.0056(16) |
| C15 | 0.064(3) | 0.046(3) | 0.062(3) | 0.013(2) | 0.046(2) | 0.029(2) |
| Cl1 | 0.0254(4) | 0.0164(4) | 0.0212(4) | 0.0057(3) | 0.0120(3) | 0.0036(3) |
| Cl2 | 0.0159(4) | 0.0300(5) | 0.0169(4) | -0.0026(3) | 0.0048(3) | -0.0014(3) |
| N1 | 0.0181(14) | 0.0162(15) | 0.0155(14) | 0.0012(11) | 0.0065(13) | -0.0016(12) |
| Ru1 | 0.01479(14) | 0.01206(14) | 0.01102(14) | 0.00033(10) | 0.00568(10) | 0.00020(10) |
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Table 8. Hydrogen atomic coordinates and isotropic atomic displacement
parameters (Å2) for 03551.
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| x/a | y/b | z/c | U(eq) |
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| H1 | 0.8930 | 0.5538 | 0.4021 | 0.019000 |
| H3 | 0.6157 | 0.3300 | 0.2012 | 0.023000 |
| H4 | 0.4651 | 0.5190 | 0.1620 | 0.023000 |
| H5 | 0.5245 | 0.7283 | 0.2392 | 0.019000 |
| H8 | 0.8488 | 0.9103 | 0.3470 | 0.021000 |
| H9 | 0.8575 | 1.0712 | 0.4577 | 0.025000 |
| H10 | 0.7428 | 1.0332 | 0.5670 | 0.027000 |
| H11 | 0.6310 | 0.8280 | 0.5703 | 0.024000 |
| H13 | 0.8109 | 0.2289 | 0.3212 | 0.027000 |
| H14A | 1.0333 | 0.2312 | 0.4257 | 0.050000 |
| H14B | 0.9370 | 0.3350 | 0.4591 | 0.050000 |
| H14C | 1.0483 | 0.3890 | 0.4116 | 0.050000 |
| H15A | 0.9985 | 0.2028 | 0.2588 | 0.078000 |
| H15B | 0.9978 | 0.3609 | 0.2404 | 0.078000 |
| H15C | 0.8671 | 0.2709 | 0.1870 | 0.078000 |
| H1A | 0.528(4) | 0.633(3) | 0.459(2) | 0.024000 |
| H2A | 0.648(3) | 0.582(3) | 0.509(2) | 0.024000 |
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Table 9. Hydrogen bond distances (Å) and angles (°) for 03551.
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| Donor-H | Acceptor-H | Donor-Acceptor | Angle |
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| N1-H1A...Cl1#1 | 0.78(3) | 2.61(3) | 3.301(3) | 148.(3) |
| N1-H2A...Cl2#1 | 0.83(3) | 2.63(3) | 3.344(3) | 145.(3) |
Symmetry transformations used to generate equivalent atoms: