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The title compound, [Ru(C12H14NO2)Cl(η6-C6H6)], exhibits a half-sandwich tripod stand structure and crystallizes in the ortho­rhom­bic space group P212121. The arene group is η6 π-coordinated to the Ru atom with a centroid-to-metal distance of 1.6590 (5) Å, with the (S)-2-(4-isopropyl-4,5-di­hydro­oxazol-2-yl)phenolate chelate ligand forming a bite angle of 86.88 (19)° through its N and phenolate O atoms. The pseudo-octa­hedral geometry assumed by the complex is completed by a chloride ligand. The coordination of the optically pure bidentate ligand induces metal centered chirality onto the complex with a Flack parameter of −0.056.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S241431462400720X/zl4075sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S241431462400720X/zl4075Isup4.hkl
Contains datablock I

CCDC reference: 2372332

Computing details top

(η6-Benzene)chlorido[(S)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)phenolato]ruthenium(II) top
Crystal data top
[Ru(C12H14NO2)Cl(C6H6)]Dx = 1.632 Mg m3
Mr = 418.87Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 1424 reflections
a = 6.5669 (18) Åθ = 2.6–22.4°
b = 9.414 (3) ŵ = 1.09 mm1
c = 27.570 (9) ÅT = 293 K
V = 1704.5 (9) Å3Plate, orange
Z = 40.47 × 0.18 × 0.15 mm
F(000) = 848
Data collection top
Bruker APEXII CCD
diffractometer
2937 reflections with I > 2σ(I)
Detector resolution: φ and ω scans pixels mm-1Rint = 0.053
Bruker APEXII CCD scansθmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 86
Tmin = 0.662, Tmax = 0.746k = 1212
9005 measured reflectionsl = 3626
4074 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0264P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.002
4074 reflectionsΔρmax = 0.66 e Å3
210 parametersΔρmin = 0.41 e Å3
0 restraintsAbsolute structure: Flack x determined using 934 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: dualAbsolute structure parameter: 0.05 (6)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The structure solution and refinement were implemented using WinGX software program (Farrugia, 2012). The highest peak and deepest hole are 0.66 and -0.41 e Å-3, respectively, which are 1.13 and 0.83 Å away from the ruthenium center. The refinement of the hydrogen atoms was performed isotropically in their idealized geometry while sitting and riding on their anisotropically refined parent atoms with Uiso = 1.2Ueq for the aromatic and methine protons, and Uiso = 1.5Ueq for the methyl protons.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2589 (12)1.2854 (9)0.8188 (3)0.047 (2)
H1A0.3794571.3206780.8351650.057*
H1B0.2677891.3094920.7846130.057*
C20.2375 (11)1.1261 (8)0.8256 (2)0.0362 (17)
H20.3646171.0868110.8384710.043*
C30.1761 (10)1.0454 (9)0.7791 (2)0.0409 (19)
H30.1377530.9486220.7884520.049*
C40.0048 (18)1.1122 (8)0.7531 (2)0.0508 (17)
H4A0.0300431.2067610.7430360.076*
H4B0.1192131.1159280.7747740.076*
H4C0.0392251.0561710.7252380.076*
C50.3629 (12)1.0355 (12)0.7454 (3)0.070 (3)
H5A0.3336020.9719680.7191310.105*
H5B0.4775091.0004710.7634430.105*
H5C0.3939651.1280340.7327860.105*
C60.0089 (13)1.2403 (6)0.86639 (19)0.0312 (13)
C70.1874 (9)1.2786 (7)0.8950 (2)0.0316 (16)
C80.2721 (11)1.4153 (8)0.8885 (2)0.0394 (17)
H80.2121651.4776390.8665310.047*
C90.4400 (11)1.4573 (9)0.9137 (3)0.053 (2)
H90.4984661.5458250.9081800.064*
C100.5219 (15)1.3655 (9)0.9478 (3)0.056 (2)
H100.6325141.3953620.9662500.067*
C110.4456 (10)1.2333 (9)0.9552 (3)0.047 (2)
H110.5064471.1743170.9780420.057*
C120.2755 (10)1.1833 (8)0.9288 (2)0.0319 (16)
C130.2044 (11)0.9128 (8)0.9641 (2)0.0424 (19)
H130.2386070.9790150.9877440.051*
C140.0350 (12)0.8234 (7)0.9705 (2)0.042 (2)
H140.0414860.8302650.9988370.050*
C150.0200 (14)0.7245 (7)0.9352 (2)0.0456 (18)
H150.1302350.6642620.9402330.055*
C160.0933 (11)0.7167 (8)0.8916 (3)0.047 (2)
H160.0528120.6544500.8672150.057*
C170.2667 (11)0.8025 (8)0.8847 (3)0.0443 (19)
H170.3437410.7943850.8565570.053*
C180.3229 (10)0.9013 (8)0.9212 (3)0.043 (2)
H180.4370090.9585220.9169530.052*
N10.0747 (7)1.1175 (6)0.86312 (18)0.0311 (14)
O10.2134 (7)1.0558 (5)0.93758 (15)0.0381 (11)
O20.0756 (7)1.3444 (5)0.84022 (17)0.0456 (14)
Cl10.2594 (3)0.8953 (2)0.84198 (6)0.0507 (5)
Ru10.00224 (9)0.93480 (5)0.90217 (2)0.02858 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.044 (5)0.057 (5)0.040 (4)0.015 (4)0.012 (4)0.001 (4)
C20.027 (4)0.054 (5)0.027 (3)0.001 (4)0.008 (3)0.000 (3)
C30.040 (4)0.047 (5)0.036 (4)0.006 (4)0.010 (3)0.003 (4)
C40.052 (4)0.061 (5)0.039 (3)0.005 (8)0.013 (4)0.001 (3)
C50.061 (6)0.106 (9)0.044 (5)0.030 (6)0.012 (4)0.004 (5)
C60.041 (4)0.028 (3)0.025 (3)0.010 (5)0.001 (4)0.001 (2)
C70.027 (4)0.037 (4)0.030 (4)0.000 (3)0.000 (3)0.012 (3)
C80.045 (4)0.038 (4)0.036 (4)0.003 (4)0.008 (3)0.004 (3)
C90.054 (6)0.048 (5)0.058 (5)0.017 (4)0.015 (4)0.021 (4)
C100.045 (5)0.066 (5)0.055 (4)0.011 (6)0.008 (5)0.026 (4)
C110.043 (6)0.049 (5)0.051 (4)0.002 (4)0.014 (3)0.017 (4)
C120.029 (4)0.038 (4)0.029 (3)0.001 (3)0.003 (3)0.013 (3)
C130.040 (4)0.047 (5)0.040 (4)0.002 (4)0.014 (3)0.008 (4)
C140.050 (6)0.041 (4)0.035 (3)0.003 (4)0.007 (4)0.012 (3)
C150.046 (5)0.035 (4)0.056 (4)0.010 (5)0.008 (5)0.013 (3)
C160.052 (5)0.035 (4)0.056 (5)0.001 (4)0.001 (4)0.003 (4)
C170.029 (4)0.045 (5)0.059 (5)0.008 (4)0.009 (4)0.001 (4)
C180.027 (4)0.044 (5)0.059 (5)0.001 (3)0.004 (3)0.010 (4)
N10.019 (3)0.047 (4)0.028 (3)0.008 (3)0.005 (2)0.001 (3)
O10.039 (3)0.037 (3)0.039 (2)0.001 (3)0.017 (2)0.002 (2)
O20.049 (3)0.043 (3)0.046 (3)0.007 (2)0.012 (2)0.008 (2)
Cl10.0276 (10)0.0772 (16)0.0475 (10)0.0096 (10)0.0033 (8)0.0106 (10)
Ru10.0237 (2)0.0325 (2)0.0295 (2)0.0020 (4)0.0034 (3)0.0008 (2)
Geometric parameters (Å, º) top
C1—O21.452 (8)C9—C101.386 (11)
C1—C21.519 (10)C9—H90.9300
C1—H1A0.9700C10—C111.357 (11)
C1—H1B0.9700C10—H100.9300
C2—N11.490 (7)C11—C121.414 (9)
C2—C31.542 (9)C11—H110.9300
C2—H20.9800C12—O11.291 (8)
C3—C41.523 (12)C13—C141.406 (9)
C3—C51.541 (9)C13—C181.420 (9)
C3—H30.9800C13—H130.9300
C4—H4A0.9600C14—C151.396 (9)
C4—H4B0.9600C14—H140.9300
C4—H4C0.9600C15—C161.416 (10)
C5—H5A0.9600C15—H150.9300
C5—H5B0.9600C16—C171.409 (10)
C5—H5C0.9600C16—H160.9300
C6—N11.282 (8)C17—C181.418 (10)
C6—O21.338 (7)C17—H170.9300
C6—C71.458 (10)C18—H180.9300
C7—C81.413 (9)N1—Ru12.084 (6)
C7—C121.418 (9)O1—Ru12.063 (5)
C8—C91.363 (9)Cl1—Ru12.4176 (19)
C8—H80.9300
O2—C1—C2104.5 (6)C8—C9—C10118.6 (8)
O2—C1—H1A110.9C8—C9—H9120.7
C2—C1—H1A110.9C10—C9—H9120.7
O2—C1—H1B110.9C11—C10—C9122.0 (8)
C2—C1—H1B110.9C11—C10—H10119.0
H1A—C1—H1B108.9C9—C10—H10119.0
N1—C2—C1101.9 (6)C10—C11—C12121.4 (8)
N1—C2—C3111.3 (5)C10—C11—H11119.3
C1—C2—C3114.1 (6)C12—C11—H11119.3
N1—C2—H2109.8O1—C12—C11117.5 (7)
C1—C2—H2109.8O1—C12—C7125.7 (6)
C3—C2—H2109.8C11—C12—C7116.7 (7)
C4—C3—C5111.3 (6)C14—C13—C18119.6 (7)
C4—C3—C2113.0 (6)C14—C13—H13120.2
C5—C3—C2108.8 (6)C18—C13—H13120.2
C4—C3—H3107.9C15—C14—C13121.0 (7)
C5—C3—H3107.9C15—C14—H14119.5
C2—C3—H3107.9C13—C14—H14119.5
C3—C4—H4A109.5C14—C15—C16119.5 (7)
C3—C4—H4B109.5C14—C15—H15120.3
H4A—C4—H4B109.5C16—C15—H15120.3
C3—C4—H4C109.5C17—C16—C15120.6 (7)
H4A—C4—H4C109.5C17—C16—H16119.7
H4B—C4—H4C109.5C15—C16—H16119.7
C3—C5—H5A109.5C16—C17—C18119.5 (7)
C3—C5—H5B109.5C16—C17—H17120.3
H5A—C5—H5B109.5C18—C17—H17120.3
C3—C5—H5C109.5C17—C18—C13119.8 (7)
H5A—C5—H5C109.5C17—C18—H18120.1
H5B—C5—H5C109.5C13—C18—H18120.1
N1—C6—O2116.4 (7)C6—N1—C2107.9 (6)
N1—C6—C7127.3 (6)C6—N1—Ru1127.6 (4)
O2—C6—C7116.3 (6)C2—N1—Ru1124.5 (5)
C8—C7—C12120.0 (6)C12—O1—Ru1129.9 (4)
C8—C7—C6118.3 (6)C6—O2—C1106.5 (6)
C12—C7—C6121.8 (6)O1—Ru1—N186.9 (2)
C9—C8—C7121.2 (7)O1—Ru1—Cl185.52 (14)
C9—C8—H8119.4N1—Ru1—Cl186.26 (15)
C7—C8—H8119.4
O2—C1—C2—N116.4 (7)C6—C7—C12—C11178.7 (6)
O2—C1—C2—C3103.6 (6)C18—C13—C14—C150.7 (11)
N1—C2—C3—C465.7 (8)C13—C14—C15—C161.7 (11)
C1—C2—C3—C448.8 (9)C14—C15—C16—C173.3 (11)
N1—C2—C3—C5170.2 (6)C15—C16—C17—C182.5 (11)
C1—C2—C3—C575.2 (8)C16—C17—C18—C130.1 (11)
N1—C6—C7—C8171.5 (7)C14—C13—C18—C171.5 (11)
O2—C6—C7—C87.7 (9)O2—C6—N1—C25.5 (8)
N1—C6—C7—C128.9 (11)C7—C6—N1—C2173.7 (6)
O2—C6—C7—C12172.0 (6)O2—C6—N1—Ru1174.7 (4)
C12—C7—C8—C90.9 (10)C7—C6—N1—Ru16.2 (10)
C6—C7—C8—C9179.4 (6)C1—C2—N1—C613.7 (7)
C7—C8—C9—C102.9 (11)C3—C2—N1—C6108.3 (7)
C8—C9—C10—C113.0 (13)C1—C2—N1—Ru1166.5 (4)
C9—C10—C11—C121.1 (13)C3—C2—N1—Ru171.5 (7)
C10—C11—C12—O1179.3 (7)C11—C12—O1—Ru1171.7 (4)
C10—C11—C12—C70.9 (10)C7—C12—O1—Ru18.6 (10)
C8—C7—C12—O1179.3 (6)N1—C6—O2—C15.9 (8)
C6—C7—C12—O11.1 (10)C7—C6—O2—C1174.8 (6)
C8—C7—C12—C111.0 (9)C2—C1—O2—C614.2 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O20.932.382.725 (9)102
C17—H17···Cl1i0.932.803.440 (8)127
C18—H18···O1i0.932.543.405 (8)156
Symmetry code: (i) x+1, y, z.
 

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