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The intramolecular distances in the title compound, [Mn(C8H14)(C6H7)(CO)2], are typical for this type of complex, with Mn—CCp in the range 2.128 (3)–2.166 (3) Å, Mn—Cdouble bond 2.203 (3) and 2.211 (3) Å, and Mn—CCO 1.768 (3) and 1.778 (3) Å. The methyl substituent of the cyclo­penta­dienyl ring eclipses a carbonyl ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301626X/wn6175sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301626X/wn6175Isup2.hkl
Contains datablock I

CCDC reference: 221659

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.047
  • wR factor = 0.132
  • Data-to-parameter ratio = 24.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
ABSTM_02 Alert B The ratio of Tmax/Tmin expected RT(exp) is > 1.20 Absorption corrections should be applied. Tmin and Tmax expected: 0.596 0.739 RT(exp) = 1.240
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: Nicolet P3 Software (Nicolet, 1980); cell refinement: Nicolet P3 Software; data reduction: RDNIC (Howie, 1980); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Dicarbonyl(η2-cis-cyclooctene)(η5-methylcyclopentadienyl)manganese(I) top
Crystal data top
[Mn(C8H14)(C6H7)(CO)2]F(000) = 632
Mr = 300.27Dx = 1.350 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.198 (5) ÅCell parameters from 14 reflections
b = 19.476 (13) Åθ = 10.5–11.6°
c = 12.273 (10) ŵ = 0.89 mm1
β = 94.21 (6)°T = 298 K
V = 1478 (2) Å3Block, yellow
Z = 40.60 × 0.58 × 0.34 mm
Data collection top
Nicolet P3
diffractometer
Rint = 0.016
Radiation source: normal-focus sealed tubeθmax = 30.0°, θmin = 2.0°
Graphite monochromatorh = 08
ω scansk = 027
4669 measured reflectionsl = 1717
4318 independent reflections2 standard reflections every 50 reflections
3177 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0698P)2 + 0.2713P]
where P = (Fo2 + 2Fc2)/3
4318 reflections(Δ/σ)max < 0.001
180 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.53 e Å3
Special details top

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

-2.1687(0.0084)x - 18.2447(0.0213)y + 0.3656(0.0169)z = 0.9632(0.0049)

* 0.0046 (0.0016) C9 * -0.0027 (0.0017) C10 * -0.0002 (0.0018) C11 * 0.0030 (0.0018) C12 * -0.0047 (0.0017) C13 0.1097 (0.0055) C14 - 1.7925 (0.0022) Mn1

Rms deviation of fitted atoms = 0.0035

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Mn10.13086 (5)0.035414 (16)0.27508 (3)0.04136 (12)
C10.0693 (4)0.12211 (11)0.3236 (2)0.0490 (5)
H10.13040.08400.35510.059*
C20.0184 (5)0.17883 (13)0.3975 (2)0.0650 (7)
H2A0.13840.20110.36530.078*
H2B0.07120.15990.46750.078*
C30.1619 (7)0.23189 (17)0.4141 (3)0.0943 (11)
H3A0.09570.27250.44780.113*0.687 (8)
H3B0.25830.21280.46500.113*0.687 (8)
H3C0.13600.25330.48520.113*0.313 (8)
H3D0.30060.20870.41230.113*0.313 (8)
C40.2997 (10)0.2542 (3)0.3089 (7)0.107 (3)0.687 (8)
H4A0.37810.21450.27910.128*0.687 (8)
H4B0.40570.28770.32880.128*0.687 (8)
C4A0.169 (3)0.2878 (9)0.3240 (13)0.107*0.313 (8)
H4C0.02230.30170.31130.128*0.313 (8)
H4D0.24540.32780.34810.128*0.313 (8)
C50.1735 (13)0.2842 (3)0.2220 (7)0.107 (3)0.687 (8)
H5A0.03310.29790.25500.129*0.687 (8)
H5B0.24680.32550.19520.129*0.687 (8)
C5A0.284 (3)0.2599 (10)0.2153 (15)0.107*0.313 (8)
H5C0.36990.22030.23270.129*0.313 (8)
H5D0.38340.29490.18580.129*0.313 (8)
C60.1379 (8)0.23922 (18)0.1260 (3)0.1059 (13)
H6A0.09050.26750.06720.127*0.687 (8)
H6B0.27450.21830.10060.127*0.687 (8)
H6C0.06070.27990.10500.127*0.313 (8)
H6D0.23010.22500.06270.127*0.313 (8)
C70.0297 (6)0.18220 (15)0.1512 (3)0.0756 (8)
H7A0.08060.16530.08330.091*
H7B0.15270.20100.19460.091*
C80.0635 (4)0.12390 (12)0.2116 (2)0.0509 (5)
H80.12060.08680.17140.061*
C90.1261 (5)0.06411 (13)0.1961 (2)0.0574 (6)
C100.2007 (5)0.07039 (12)0.3049 (2)0.0629 (7)
H100.33720.08580.33040.076*
C110.0370 (9)0.04978 (15)0.3693 (3)0.0928 (14)
H110.04430.04910.44530.111*
C120.1394 (6)0.03038 (15)0.2997 (5)0.1042 (17)
H120.27170.01460.32080.125*
C130.0830 (6)0.03880 (14)0.1931 (4)0.0821 (10)
H130.17080.02910.13020.098*
C140.2443 (9)0.0859 (2)0.0996 (3)0.1247 (18)
H14A0.39680.07890.11520.187*
H14B0.19510.05900.03700.187*
H14C0.21690.13360.08480.187*
C150.3180 (4)0.06540 (13)0.3812 (2)0.0535 (5)
O10.4416 (3)0.08206 (12)0.45064 (17)0.0773 (6)
C160.3013 (4)0.06400 (14)0.1749 (2)0.0567 (6)
O20.4153 (3)0.07884 (13)0.10807 (18)0.0864 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.03969 (17)0.03585 (17)0.04957 (19)0.00130 (12)0.01031 (12)0.00070 (13)
C10.0495 (12)0.0346 (10)0.0647 (14)0.0013 (8)0.0166 (10)0.0013 (9)
C20.0876 (19)0.0462 (13)0.0616 (15)0.0078 (13)0.0089 (13)0.0090 (11)
C30.124 (3)0.0624 (18)0.099 (3)0.027 (2)0.027 (2)0.0166 (18)
C40.077 (3)0.066 (3)0.183 (7)0.031 (3)0.044 (4)0.007 (4)
C50.112 (5)0.047 (3)0.163 (7)0.031 (3)0.016 (5)0.022 (3)
C60.152 (4)0.069 (2)0.096 (3)0.034 (2)0.004 (3)0.0315 (19)
C70.096 (2)0.0614 (16)0.0705 (17)0.0105 (15)0.0174 (16)0.0236 (14)
C80.0493 (11)0.0425 (11)0.0599 (13)0.0039 (9)0.0020 (10)0.0000 (9)
C90.0766 (17)0.0430 (12)0.0529 (13)0.0056 (11)0.0074 (11)0.0085 (10)
C100.0835 (18)0.0401 (12)0.0640 (15)0.0086 (12)0.0028 (13)0.0007 (10)
C110.172 (4)0.0428 (14)0.0709 (19)0.0247 (19)0.058 (2)0.0031 (13)
C120.074 (2)0.0391 (14)0.208 (5)0.0153 (14)0.069 (3)0.012 (2)
C130.0666 (18)0.0457 (14)0.128 (3)0.0123 (13)0.0303 (19)0.0029 (16)
C140.211 (5)0.087 (3)0.084 (2)0.018 (3)0.060 (3)0.035 (2)
C150.0466 (12)0.0554 (13)0.0590 (14)0.0013 (10)0.0081 (10)0.0055 (11)
O10.0605 (11)0.0977 (16)0.0713 (13)0.0065 (11)0.0109 (10)0.0002 (11)
C160.0475 (12)0.0608 (14)0.0633 (15)0.0024 (11)0.0138 (11)0.0014 (11)
O20.0729 (13)0.1103 (18)0.0810 (14)0.0134 (12)0.0392 (11)0.0037 (12)
Geometric parameters (Å, º) top
Mn1—C161.768 (3)C5—H5B0.9700
Mn1—C151.778 (3)C5A—C61.527 (18)
Mn1—C112.128 (3)C5A—H5C0.9700
Mn1—C102.132 (3)C5A—H5D0.9700
Mn1—C122.148 (3)C6—C71.536 (5)
Mn1—C132.159 (3)C6—H6A0.9700
Mn1—C92.166 (3)C6—H6B0.9700
Mn1—C12.203 (2)C6—H6C0.9700
Mn1—C82.211 (3)C6—H6D0.9700
C1—C81.378 (3)C7—C81.495 (4)
C1—C21.505 (3)C7—H7A0.9700
C1—H10.9300C7—H7B0.9700
C2—C31.546 (4)C8—H80.9300
C2—H2A0.9700C9—C131.384 (4)
C2—H2B0.9700C9—C101.386 (4)
C3—C4A1.551 (17)C9—C141.498 (4)
C3—C41.558 (9)C10—C111.391 (5)
C3—H3A0.9700C10—H100.9300
C3—H3B0.9700C11—C121.390 (6)
C3—H3C0.9700C11—H110.9300
C3—H3D0.9700C12—C131.390 (7)
C4—C51.488 (10)C12—H120.9300
C4—H4A0.9700C13—H130.9300
C4—H4B0.9700C14—H14A0.9600
C4A—C5A1.56 (3)C14—H14B0.9600
C4A—H4C0.9700C14—H14C0.9600
C4A—H4D0.9700C15—O11.150 (3)
C5—C61.498 (8)C16—O21.158 (3)
C5—H5A0.9700
C16—Mn1—C1590.85 (13)C4—C5—H5A108.1
C16—Mn1—C11145.52 (14)C6—C5—H5A108.1
C15—Mn1—C1192.72 (16)C4—C5—H5B108.1
C16—Mn1—C10107.42 (12)C6—C5—H5B108.1
C15—Mn1—C1094.51 (12)H5A—C5—H5B107.3
C11—Mn1—C1038.11 (13)C6—C5A—C4A116.5 (15)
C16—Mn1—C12142.90 (18)C6—C5A—H5C108.2
C15—Mn1—C12124.50 (19)C4A—C5A—H5C108.2
C11—Mn1—C1237.93 (17)C6—C5A—H5D108.2
C10—Mn1—C1263.24 (14)C4A—C5A—H5D108.2
C16—Mn1—C13105.32 (16)H5C—C5A—H5D107.3
C15—Mn1—C13155.02 (13)C5—C6—C7113.6 (4)
C11—Mn1—C1363.17 (16)C5A—C6—C7118.3 (7)
C10—Mn1—C1362.80 (12)C5—C6—H6A108.8
C12—Mn1—C1337.64 (18)C7—C6—H6A108.8
C16—Mn1—C987.70 (12)C5—C6—H6B108.8
C15—Mn1—C9127.48 (11)C7—C6—H6B108.8
C11—Mn1—C963.28 (12)H6A—C6—H6B107.7
C10—Mn1—C937.61 (11)C5A—C6—H6C107.7
C12—Mn1—C962.88 (13)C7—C6—H6C107.7
C13—Mn1—C937.32 (12)C5A—C6—H6D107.7
C16—Mn1—C1108.87 (11)C7—C6—H6D107.7
C15—Mn1—C184.27 (11)H6C—C6—H6D107.1
C11—Mn1—C1105.60 (13)C8—C7—C6111.6 (3)
C10—Mn1—C1143.70 (10)C8—C7—H7A109.3
C12—Mn1—C187.64 (12)C6—C7—H7A109.3
C13—Mn1—C1107.50 (13)C8—C7—H7B109.3
C9—Mn1—C1144.82 (11)C6—C7—H7B109.3
C16—Mn1—C881.23 (12)H7A—C7—H7B108.0
C15—Mn1—C8108.13 (11)C1—C8—C7123.6 (2)
C11—Mn1—C8129.47 (16)C1—C8—Mn171.49 (13)
C10—Mn1—C8155.83 (11)C7—C8—Mn1123.12 (19)
C12—Mn1—C895.99 (15)C1—C8—H8118.2
C13—Mn1—C893.31 (12)C7—C8—H8118.2
C9—Mn1—C8123.40 (11)Mn1—C8—H876.0
C1—Mn1—C836.37 (9)C13—C9—C10107.6 (3)
C8—C1—C2123.2 (2)C13—C9—C14126.2 (4)
C8—C1—Mn172.14 (13)C10—C9—C14126.0 (3)
C2—C1—Mn1122.67 (18)C13—C9—Mn171.06 (16)
C8—C1—H1118.4C10—C9—Mn169.83 (14)
C2—C1—H1118.4C14—C9—Mn1128.0 (2)
Mn1—C1—H175.8C9—C10—C11108.5 (3)
C1—C2—C3109.7 (3)C9—C10—Mn172.55 (15)
C1—C2—H2A109.7C11—C10—Mn170.80 (16)
C3—C2—H2A109.7C9—C10—H10125.8
C1—C2—H2B109.7C11—C10—H10125.8
C3—C2—H2B109.7Mn1—C10—H10122.5
H2A—C2—H2B108.2C12—C11—C10107.6 (3)
C2—C3—C4A110.9 (7)C12—C11—Mn171.81 (18)
C2—C3—C4115.8 (3)C10—C11—Mn171.09 (16)
C2—C3—H3A108.3C12—C11—H11126.2
C4—C3—H3A108.3C10—C11—H11126.2
C2—C3—H3B108.3Mn1—C11—H11122.6
C4—C3—H3B108.3C13—C12—C11107.8 (3)
H3A—C3—H3B107.4C13—C12—Mn171.62 (18)
C2—C3—H3C109.5C11—C12—Mn170.26 (19)
C4A—C3—H3C109.5C13—C12—H12126.1
C2—C3—H3D109.5C11—C12—H12126.1
C4A—C3—H3D109.5Mn1—C12—H12123.7
H3C—C3—H3D108.0C9—C13—C12108.5 (3)
C5—C4—C3114.8 (6)C9—C13—Mn171.61 (16)
C5—C4—H4A108.6C12—C13—Mn170.74 (19)
C3—C4—H4A108.6C9—C13—H13125.8
C5—C4—H4B108.6C12—C13—H13125.8
C3—C4—H4B108.6Mn1—C13—H13123.5
H4A—C4—H4B107.6C9—C14—H14A109.5
C3—C4A—C5A110.6 (15)C9—C14—H14B109.5
C3—C4A—H4C109.5H14A—C14—H14B109.5
C5A—C4A—H4C109.5C9—C14—H14C109.5
C3—C4A—H4D109.5H14A—C14—H14C109.5
C5A—C4A—H4D109.5H14B—C14—H14C109.5
H4C—C4A—H4D108.1O1—C15—Mn1177.2 (2)
C4—C5—C6116.7 (6)O2—C16—Mn1176.1 (3)
C8—C1—C2—C390.1 (3)C5A—C6—C7—C842.7 (9)
C1—C2—C3—C4A88.4 (8)C2—C1—C8—C70.2 (4)
C1—C2—C3—C445.6 (5)C6—C7—C8—C186.2 (4)
C2—C3—C4—C557.7 (6)C13—C9—C10—C110.7 (3)
C2—C3—C4A—C5A78.1 (14)C14—C9—C10—C11175.0 (3)
C3—C4—C5—C6104.1 (8)C9—C10—C11—C120.2 (3)
C3—C4A—C5A—C6102.6 (17)C10—C11—C12—C130.3 (3)
C4—C5—C6—C774.0 (8)C10—C9—C13—C120.9 (3)
C4A—C5A—C6—C760.1 (18)C14—C9—C13—C12174.8 (3)
C5—C6—C7—C877.9 (5)C11—C12—C13—C90.8 (3)
Selected bond lengths and angles (Å, °) for (I). top
Mn1—Cga1.793 (3)Mn1—C151.778 (3)
Mn1—Mba2.097 (3)Mn1—C161.768 (3)
Mn1—C12.203 (2)Mn1—C82.211 (3)
C15—O11.150 (3)C16—O21.158 (3)
C1—C81.378 (3)
Cg—Mn—Mb123.74 (8)Mb—Mn—C1596.42 (12)
Cg—Mn—C15122.07 (10)Mb—Mn—C1695.14(12
Cg—Mn—C16120.79 (10)C15—Mn—C1690.86 (13)
Mn—C15—O1177.2 (2)Mn—C16—O2176.1 (3)
C1—Mn—C836.37 (9)
Note: (a) Cg and Mb are, respectively, the centroid of the cyclopentadienyl ring and the mid-point of the C1C8 bond.
 

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