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The title complex, [Cr(C10H15N)(CO)3], has a typical three-legged piano-stool structure, as is expected for an η6-arene–tri­carbonyl­chromium compound. The conformation is staggered with respect to the side chain and one of the carbonyl ligands. The side chain bearing the stereogenic centre adopts a conformation with the H atom pointing downwards, leaving the di­methyl­amine group above the ring plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501007X/bt6636sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501007X/bt6636Isup2.hkl
Contains datablock I

CCDC reference: 257372

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.022
  • wR factor = 0.061
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

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Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cr - C2 .. 13.09 su
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.63 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C2 .. 5.82 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr - C1 .. 9.96 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr - C3 .. 8.58 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 2869 Count of symmetry unique reflns 1656 Completeness (_total/calc) 173.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1213 Fraction of Friedel pairs measured 0.732 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Tricarbonyl[η6-(R)—N,N-dimethyl-1-phenylethylamine]chromium(0) top
Crystal data top
[Cr(C10H15N)(CO)3]Dx = 1.439 Mg m3
Mr = 285.26Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 8096 reflections
a = 10.6453 (18) Åθ = 2.6–27.0°
b = 10.7928 (19) ŵ = 0.87 mm1
c = 11.458 (2) ÅT = 110 K
V = 1316.5 (4) Å3Irregular, yellow
Z = 40.63 × 0.37 × 0.13 mm
F(000) = 592
Data collection top
Bruker SMART APEX CCD
diffractometer
2869 independent reflections
Radiation source: fine-focus sealed tube2807 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 27.0°, θmin = 2.6°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick; 1996)
h = 1313
Tmin = 0.611, Tmax = 0.892k = 1313
16290 measured reflectionsl = 1414
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)] = 0.022H-atom parameters constrained
wR(F2) = 0.061 w = 1/[σ2(Fo2) + (0.075P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2869 reflectionsΔρmax = 0.31 e Å3
165 parametersΔρmin = 0.20 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.003 (14)
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.

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 > 2σ(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*/Ueq
Cr0.08080 (2)0.65049 (2)0.40503 (2)0.01493 (8)
N0.10067 (13)0.28621 (12)0.50858 (12)0.0214 (3)
C20.06402 (16)0.81274 (15)0.45411 (14)0.0226 (3)
C30.15152 (15)0.61564 (14)0.54632 (15)0.0207 (3)
C130.04410 (15)0.45556 (14)0.35475 (14)0.0179 (3)
H130.09420.38370.36630.022*
C50.08674 (19)0.19131 (16)0.59843 (17)0.0314 (4)
H5A0.14600.20760.66210.047*
H5B0.00070.19290.62890.047*
H5C0.10420.10970.56470.047*
C70.05696 (15)0.40835 (14)0.54878 (13)0.0195 (3)
H70.03030.39590.57880.023*
C110.01570 (15)0.63279 (14)0.23354 (13)0.0198 (3)
H110.00630.68010.16420.024*
C80.04531 (14)0.49069 (14)0.44076 (13)0.0166 (3)
C10.23984 (16)0.68468 (15)0.34757 (14)0.0235 (3)
C120.05885 (15)0.52646 (14)0.25281 (14)0.0188 (3)
H120.11950.50270.19630.023*
O30.19367 (13)0.59268 (12)0.63658 (11)0.0311 (3)
C100.10346 (14)0.66710 (14)0.31814 (13)0.0199 (3)
H100.15310.73920.30660.024*
C90.11957 (14)0.59590 (14)0.42094 (14)0.0187 (3)
H90.18100.61960.47680.022*
C60.13158 (19)0.46736 (17)0.64836 (15)0.0274 (4)
H6A0.13520.40990.71450.041*
H6B0.21700.48570.62160.041*
H6C0.09040.54430.67280.041*
O10.33899 (13)0.70305 (14)0.31265 (12)0.0357 (3)
C40.22907 (17)0.28726 (17)0.46319 (17)0.0299 (4)
H4A0.25040.20480.43340.045*
H4B0.23550.34800.39990.045*
H4C0.28740.30970.52590.045*
O20.05518 (13)0.91323 (11)0.48709 (12)0.0336 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr0.01446 (12)0.01332 (11)0.01700 (12)0.00046 (9)0.00053 (9)0.00105 (9)
N0.0234 (7)0.0191 (6)0.0217 (6)0.0030 (5)0.0040 (6)0.0017 (5)
C20.0222 (8)0.0219 (7)0.0236 (7)0.0009 (6)0.0038 (6)0.0001 (6)
C30.0188 (8)0.0176 (7)0.0256 (8)0.0009 (6)0.0024 (7)0.0019 (6)
C130.0175 (7)0.0156 (7)0.0208 (7)0.0001 (5)0.0002 (6)0.0024 (6)
C50.0388 (10)0.0217 (7)0.0337 (9)0.0016 (7)0.0045 (10)0.0090 (7)
C70.0194 (8)0.0200 (7)0.0191 (7)0.0016 (6)0.0001 (6)0.0015 (6)
C110.0209 (7)0.0204 (7)0.0180 (7)0.0028 (6)0.0032 (6)0.0005 (6)
C80.0154 (7)0.0167 (7)0.0178 (7)0.0025 (5)0.0005 (5)0.0021 (5)
C10.0237 (9)0.0247 (8)0.0220 (8)0.0033 (6)0.0009 (7)0.0032 (6)
C120.0194 (8)0.0189 (7)0.0180 (7)0.0019 (6)0.0021 (6)0.0035 (5)
O30.0320 (7)0.0342 (7)0.0270 (6)0.0006 (6)0.0111 (5)0.0015 (5)
C100.0168 (7)0.0181 (7)0.0247 (8)0.0009 (6)0.0043 (6)0.0003 (6)
C90.0135 (7)0.0205 (7)0.0221 (8)0.0004 (6)0.0005 (6)0.0021 (6)
C60.0354 (10)0.0256 (8)0.0213 (8)0.0008 (7)0.0065 (7)0.0020 (7)
O10.0237 (7)0.0476 (8)0.0356 (7)0.0107 (6)0.0053 (6)0.0042 (6)
C40.0261 (9)0.0304 (9)0.0332 (9)0.0090 (7)0.0010 (8)0.0001 (7)
O20.0407 (8)0.0186 (6)0.0417 (7)0.0036 (5)0.0064 (6)0.0075 (5)
Geometric parameters (Å, º) top
Cr—C31.8246 (17)C5—H5C0.9800
Cr—C21.8479 (17)C7—C81.529 (2)
Cr—C11.8537 (18)C7—C61.529 (2)
Cr—C102.2069 (15)C7—H71.0000
Cr—C122.2110 (15)C11—C101.396 (2)
Cr—C132.2159 (16)C11—C121.413 (2)
Cr—C92.2204 (15)C11—H110.9500
Cr—C82.2236 (15)C8—C91.402 (2)
Cr—C112.2255 (15)C1—O11.146 (2)
N—C51.460 (2)C12—H120.9500
N—C41.462 (2)C10—C91.417 (2)
N—C71.472 (2)C10—H100.9500
C2—O21.152 (2)C9—H90.9500
C3—O31.154 (2)C6—H6A0.9800
C13—C121.405 (2)C6—H6B0.9800
C13—C81.422 (2)C6—H6C0.9800
C13—H130.9500C4—H4A0.9800
C5—H5A0.9800C4—H4B0.9800
C5—H5B0.9800C4—H4C0.9800
C3—Cr—C288.00 (7)H5A—C5—H5C109.5
C3—Cr—C188.82 (7)H5B—C5—H5C109.5
C2—Cr—C190.44 (8)N—C7—C8107.03 (12)
C3—Cr—C10141.60 (7)N—C7—C6116.25 (14)
C2—Cr—C1088.53 (7)C8—C7—C6113.84 (13)
C1—Cr—C10129.45 (7)N—C7—H7106.3
C3—Cr—C12128.22 (7)C8—C7—H7106.3
C2—Cr—C12143.48 (7)C6—C7—H7106.3
C1—Cr—C1286.38 (7)C10—C11—C12118.87 (14)
C10—Cr—C1266.38 (6)C10—C11—Cr70.92 (9)
C3—Cr—C1396.18 (6)C12—C11—Cr70.88 (8)
C2—Cr—C13164.11 (7)C10—C11—H11120.6
C1—Cr—C13104.93 (7)C12—C11—H11120.6
C10—Cr—C1378.65 (6)Cr—C11—H11130.1
C12—Cr—C1337.01 (6)C9—C8—C13118.76 (14)
C3—Cr—C9105.59 (7)C9—C8—C7123.79 (14)
C2—Cr—C997.68 (7)C13—C8—C7117.43 (14)
C1—Cr—C9163.62 (7)C9—C8—Cr71.48 (9)
C10—Cr—C937.33 (6)C13—C8—Cr71.03 (9)
C12—Cr—C978.61 (6)C7—C8—Cr130.46 (10)
C13—Cr—C966.43 (6)O1—C1—Cr178.40 (15)
C3—Cr—C885.75 (6)C13—C12—C11120.64 (14)
C2—Cr—C8128.36 (7)C13—C12—Cr71.69 (9)
C1—Cr—C8140.46 (7)C11—C12—Cr71.99 (9)
C10—Cr—C867.01 (6)C13—C12—H12119.7
C12—Cr—C867.16 (6)C11—C12—H12119.7
C13—Cr—C837.35 (6)Cr—C12—H12129.0
C9—Cr—C836.78 (6)C11—C10—C9120.95 (14)
C3—Cr—C11162.97 (7)C11—C10—Cr72.36 (9)
C2—Cr—C11107.79 (7)C9—C10—Cr71.85 (9)
C1—Cr—C1197.18 (7)C11—C10—H10119.5
C10—Cr—C1136.72 (6)C9—C10—H10119.5
C12—Cr—C1137.13 (6)Cr—C10—H10128.6
C13—Cr—C1166.90 (6)C8—C9—C10120.37 (14)
C9—Cr—C1166.82 (6)C8—C9—Cr71.73 (9)
C8—Cr—C1179.47 (6)C10—C9—Cr70.82 (9)
C5—N—C4110.56 (14)C8—C9—H9119.8
C5—N—C7112.06 (13)C10—C9—H9119.8
C4—N—C7113.57 (13)Cr—C9—H9130.2
O2—C2—Cr178.36 (14)C7—C6—H6A109.5
O3—C3—Cr178.47 (15)C7—C6—H6B109.5
C12—C13—C8120.39 (14)H6A—C6—H6B109.5
C12—C13—Cr71.30 (9)C7—C6—H6C109.5
C8—C13—Cr71.62 (9)H6A—C6—H6C109.5
C12—C13—H13119.8H6B—C6—H6C109.5
C8—C13—H13119.8N—C4—H4A109.5
Cr—C13—H13129.8N—C4—H4B109.5
N—C5—H5A109.5H4A—C4—H4B109.5
N—C5—H5B109.5N—C4—H4C109.5
H5A—C5—H5B109.5H4A—C4—H4C109.5
N—C5—H5C109.5H4B—C4—H4C109.5
 

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