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The title compound, [Cr{(C6H5N(CH3)2}(CO)3], exhibits the three-legged piano-stool structure expected for a tri­carbonyl­metal with an η6-coordinated arene. The arene moiety is distorted with the amino functional group bent away from the chromium atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031484/ac6142sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031484/ac6142Isup2.hkl
Contains datablock I

CCDC reference: 262228

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.042
  • wR factor = 0.100
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.01 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 22 PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C3 .. 5.62 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - C1 .. 6.91 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - C2 .. 6.63 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - C3 .. 9.13 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr2 - C21 .. 6.57 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr2 - C22 .. 7.45 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr2 - C23 .. 7.16 su PLAT330_ALERT_2_C Large Average Phenyl C-C Dist. C4 -C9 1.41 Ang. PLAT330_ALERT_2_C Large Average Phenyl C-C Dist. C24 -C29 1.41 Ang. PLAT350_ALERT_3_C Short C-H Bond (0.96A) C27 - H27 ... 0.84 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 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, 1997–2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(η6-N,N-Dimethylaniline)tricarbonylchromium top
Crystal data top
[Cr(C8H11N)(CO)3]Z = 4
Mr = 257.21F(000) = 528
Triclinic, P1Dx = 1.553 Mg m3
a = 7.0974 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6169 (8) ÅCell parameters from 9302 reflections
c = 14.0477 (9) Åθ = 2.9–30.5°
α = 115.397 (1)°µ = 1.03 mm1
β = 90.959 (1)°T = 100 K
γ = 102.666 (1)°Plate, yellow
V = 1099.92 (13) Å30.60 × 0.15 × 0.05 mm
Data collection top
Bruker AXS SMART APEX CCD
diffractometer
5444 independent reflections
Radiation source: fine-focus sealed tube5013 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 28.3°, θmin = 1.6°
Absorption correction: multi scan
(SADABS in SAINT-Plus; Bruker, 1997-1999)
h = 99
Tmin = 0.743, Tmax = 0.95k = 1616
11969 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: difference Fourier map
wR(F2) = 0.100All H-atom parameters refined
S = 1.18 w = 1/[σ2(Fo2) + (0.0417P)2 + 0.8635P]
where P = (Fo2 + 2Fc2)/3
5444 reflections(Δ/σ)max = 0.002
377 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = 0.34 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.

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*/Ueq
Cr10.72672 (5)0.60117 (3)0.33244 (3)0.01283 (9)
Cr20.61034 (5)0.93263 (3)0.74360 (3)0.01401 (9)
O20.3690 (2)0.45802 (15)0.37291 (14)0.0230 (3)
O30.5006 (2)0.78336 (15)0.35703 (13)0.0225 (3)
O50.8926 (2)0.81234 (14)0.79190 (13)0.0220 (3)
C240.3034 (3)0.97399 (19)0.78400 (17)0.0160 (4)
C51.0327 (3)0.70715 (19)0.34094 (17)0.0162 (4)
H51.072 (4)0.757 (2)0.3092 (19)0.012 (6)*
O60.9073 (3)1.01619 (15)0.62531 (14)0.0277 (4)
N11.1256 (3)0.54308 (16)0.19661 (14)0.0161 (3)
O40.7831 (3)1.15800 (15)0.94344 (14)0.0280 (4)
N20.2450 (3)1.06830 (16)0.85889 (14)0.0172 (4)
C41.0457 (3)0.58502 (18)0.28877 (16)0.0137 (4)
C220.7840 (3)0.85962 (19)0.77417 (17)0.0164 (4)
C20.5071 (3)0.51245 (19)0.35548 (16)0.0158 (4)
C60.9670 (3)0.7529 (2)0.44121 (18)0.0204 (4)
H60.963 (4)0.829 (3)0.470 (2)0.027 (7)*
C30.5892 (3)0.71287 (19)0.34668 (16)0.0166 (4)
C270.4037 (3)0.7682 (2)0.6222 (2)0.0266 (5)
H270.433 (4)0.710 (3)0.572 (2)0.030 (8)*
C101.1645 (4)0.6168 (2)0.13939 (19)0.0220 (5)
H10A1.045 (4)0.627 (3)0.114 (2)0.030 (7)*
H10B1.230 (4)0.580 (3)0.080 (3)0.033 (8)*
H10C1.247 (4)0.698 (2)0.184 (2)0.019 (6)*
C90.9612 (3)0.5074 (2)0.33514 (18)0.0171 (4)
H90.953 (4)0.428 (3)0.300 (2)0.019 (6)*
O10.5971 (3)0.4759 (2)0.09813 (14)0.0382 (5)
C210.7165 (3)1.07166 (19)0.86570 (18)0.0187 (4)
C280.3907 (3)0.8679 (2)0.60467 (19)0.0236 (5)
H280.417 (4)0.868 (3)0.543 (2)0.024 (7)*
C230.7913 (3)0.98427 (18)0.67105 (17)0.0183 (4)
C250.3331 (3)0.8761 (2)0.80364 (19)0.0192 (4)
H250.317 (4)0.877 (2)0.867 (2)0.019 (7)*
C290.3464 (3)0.9706 (2)0.68490 (18)0.0187 (4)
H290.345 (4)1.033 (3)0.671 (2)0.021 (7)*
C310.2652 (4)1.1799 (2)0.8479 (2)0.0241 (5)
H31A0.400 (5)1.224 (3)0.856 (3)0.039 (9)*
H31B0.198 (4)1.228 (3)0.896 (2)0.032 (8)*
H31C0.209 (4)1.165 (3)0.779 (2)0.027 (7)*
C80.8939 (3)0.5546 (2)0.43469 (19)0.0215 (5)
H80.836 (4)0.503 (3)0.464 (2)0.026 (7)*
C10.6468 (3)0.5237 (2)0.18790 (18)0.0218 (5)
C70.8995 (3)0.6779 (2)0.49019 (18)0.0223 (5)
H70.856 (4)0.706 (2)0.552 (2)0.019 (7)*
C111.0997 (4)0.4133 (2)0.1336 (2)0.0252 (5)
H11A1.143 (4)0.380 (2)0.176 (2)0.022 (7)*
H11B1.187 (4)0.400 (3)0.076 (2)0.032 (8)*
H11C0.966 (5)0.369 (3)0.101 (2)0.035 (8)*
C260.3778 (3)0.7747 (2)0.7230 (2)0.0248 (5)
H260.392 (4)0.715 (3)0.738 (2)0.035 (8)*
C300.2413 (4)1.0813 (2)0.96693 (19)0.0249 (5)
H30A0.167 (4)1.009 (3)0.966 (2)0.021 (7)*
H30B0.177 (5)1.146 (3)1.008 (3)0.039 (9)*
H30C0.371 (5)1.100 (3)1.000 (2)0.030 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.01141 (16)0.01596 (17)0.01294 (17)0.00458 (12)0.00177 (12)0.00753 (13)
Cr20.01241 (16)0.01184 (16)0.01595 (17)0.00277 (12)0.00197 (12)0.00461 (13)
O20.0171 (8)0.0253 (8)0.0298 (9)0.0039 (6)0.0043 (6)0.0157 (7)
O30.0240 (8)0.0234 (8)0.0274 (8)0.0122 (7)0.0058 (7)0.0148 (7)
O50.0174 (7)0.0215 (8)0.0299 (9)0.0065 (6)0.0033 (6)0.0130 (7)
C240.0109 (9)0.0164 (9)0.0198 (10)0.0026 (7)0.0023 (8)0.0075 (8)
C50.0129 (9)0.0143 (9)0.0204 (10)0.0022 (7)0.0018 (8)0.0072 (8)
O60.0338 (9)0.0188 (8)0.0296 (9)0.0044 (7)0.0141 (8)0.0106 (7)
N10.0154 (8)0.0158 (8)0.0174 (9)0.0057 (7)0.0035 (7)0.0067 (7)
O40.0317 (9)0.0202 (8)0.0235 (9)0.0028 (7)0.0005 (7)0.0035 (7)
N20.0195 (9)0.0167 (8)0.0177 (9)0.0068 (7)0.0050 (7)0.0085 (7)
C40.0093 (8)0.0153 (9)0.0165 (9)0.0035 (7)0.0002 (7)0.0070 (8)
C220.0145 (9)0.0142 (9)0.0177 (10)0.0007 (7)0.0037 (8)0.0058 (8)
C20.0161 (10)0.0170 (10)0.0150 (9)0.0065 (8)0.0003 (8)0.0068 (8)
C60.0162 (10)0.0197 (11)0.0186 (10)0.0049 (8)0.0004 (8)0.0023 (9)
C30.0172 (10)0.0197 (10)0.0141 (9)0.0026 (8)0.0036 (8)0.0094 (8)
C270.0161 (11)0.0184 (11)0.0293 (13)0.0031 (9)0.0002 (9)0.0034 (10)
C100.0240 (11)0.0267 (12)0.0189 (11)0.0068 (10)0.0062 (9)0.0129 (10)
C90.0120 (9)0.0186 (10)0.0242 (11)0.0046 (8)0.0004 (8)0.0124 (9)
O10.0308 (10)0.0607 (13)0.0170 (9)0.0156 (9)0.0010 (7)0.0097 (9)
C210.0179 (10)0.0162 (10)0.0219 (11)0.0043 (8)0.0044 (8)0.0084 (9)
C280.0182 (11)0.0274 (12)0.0178 (11)0.0066 (9)0.0005 (9)0.0031 (9)
C230.0223 (11)0.0118 (9)0.0177 (10)0.0049 (8)0.0025 (8)0.0034 (8)
C250.0127 (10)0.0205 (10)0.0270 (12)0.0029 (8)0.0041 (8)0.0133 (9)
C290.0171 (10)0.0222 (11)0.0193 (10)0.0074 (8)0.0018 (8)0.0103 (9)
C310.0311 (13)0.0180 (11)0.0262 (12)0.0118 (10)0.0085 (10)0.0098 (10)
C80.0130 (10)0.0354 (13)0.0255 (11)0.0054 (9)0.0012 (8)0.0226 (10)
C10.0144 (10)0.0325 (12)0.0202 (11)0.0106 (9)0.0041 (8)0.0108 (10)
C70.0132 (10)0.0367 (13)0.0150 (10)0.0062 (9)0.0010 (8)0.0095 (10)
C110.0301 (13)0.0174 (11)0.0230 (12)0.0093 (10)0.0030 (10)0.0028 (9)
C260.0146 (10)0.0160 (10)0.0414 (14)0.0024 (8)0.0016 (10)0.0113 (10)
C300.0275 (12)0.0314 (13)0.0191 (11)0.0116 (10)0.0082 (9)0.0120 (10)
Geometric parameters (Å, º) top
Cr1—C31.829 (2)N2—C301.456 (3)
Cr1—C21.830 (2)N2—C311.457 (3)
Cr1—C11.848 (2)C4—C91.430 (3)
Cr1—C82.188 (2)C6—C71.403 (3)
Cr1—C62.209 (2)C6—H60.87 (3)
Cr1—C72.214 (2)C27—C261.400 (4)
Cr1—C92.252 (2)C27—C281.402 (4)
Cr1—C52.258 (2)C27—H270.84 (3)
Cr1—C42.384 (2)C10—H10A0.97 (3)
Cr2—C231.833 (2)C10—H10B0.95 (3)
Cr2—C221.836 (2)C10—H10C0.98 (3)
Cr2—C211.839 (2)C9—C81.404 (3)
Cr2—C262.197 (2)C9—H90.89 (3)
Cr2—C282.209 (2)O1—C11.148 (3)
Cr2—C272.216 (2)C28—C291.410 (3)
Cr2—C252.247 (2)C28—H280.89 (3)
Cr2—C292.258 (2)C25—C261.402 (3)
Cr2—C242.372 (2)C25—H250.90 (3)
O2—C21.161 (3)C29—H290.89 (3)
O3—C31.160 (3)C31—H31A0.97 (3)
O5—C221.155 (3)C31—H31B0.92 (3)
C24—N21.361 (3)C31—H31C0.96 (3)
C24—C291.415 (3)C8—C71.400 (4)
C24—C251.432 (3)C8—H80.94 (3)
C5—C61.406 (3)C7—H70.88 (3)
C5—C41.420 (3)C11—H11A0.94 (3)
C5—H50.91 (2)C11—H11B1.00 (3)
O6—C231.161 (3)C11—H11C0.98 (3)
N1—C41.358 (3)C26—H260.89 (3)
N1—C111.455 (3)C30—H30A0.94 (3)
N1—C101.457 (3)C30—H30B0.99 (3)
O4—C211.157 (3)C30—H30C0.96 (3)
C3—Cr1—C287.23 (9)N1—C4—C5121.42 (18)
C3—Cr1—C189.72 (10)N1—C4—C9121.94 (19)
C2—Cr1—C190.70 (10)C5—C4—C9116.56 (19)
C3—Cr1—C8138.30 (9)N1—C4—Cr1134.63 (14)
C2—Cr1—C887.63 (9)C5—C4—Cr167.41 (11)
C1—Cr1—C8131.70 (10)C9—C4—Cr167.05 (11)
C3—Cr1—C687.83 (9)O5—C22—Cr2179.0 (2)
C2—Cr1—C6132.57 (9)O2—C2—Cr1178.2 (2)
C1—Cr1—C6136.42 (10)C7—C6—C5121.4 (2)
C8—Cr1—C666.21 (9)C7—C6—Cr171.69 (13)
C3—Cr1—C7103.59 (9)C5—C6—Cr173.58 (13)
C2—Cr1—C799.45 (9)C7—C6—H6120.8 (19)
C1—Cr1—C7163.55 (9)C5—C6—H6117.7 (19)
C8—Cr1—C737.09 (9)Cr1—C6—H6124.7 (19)
C6—Cr1—C736.99 (9)O3—C3—Cr1178.88 (18)
C3—Cr1—C9164.93 (9)C26—C27—C28118.3 (2)
C2—Cr1—C9105.18 (8)C26—C27—Cr270.76 (14)
C1—Cr1—C998.48 (9)C28—C27—Cr271.26 (14)
C8—Cr1—C936.84 (8)C26—C27—H27124 (2)
C6—Cr1—C977.51 (8)C28—C27—H27117 (2)
C7—Cr1—C966.46 (9)Cr2—C27—H27126 (2)
C3—Cr1—C5101.01 (9)N1—C10—H10A111.6 (17)
C2—Cr1—C5164.88 (9)N1—C10—H10B110.7 (18)
C1—Cr1—C5101.90 (9)H10A—C10—H10B108 (2)
C8—Cr1—C577.78 (8)N1—C10—H10C112.6 (15)
C6—Cr1—C536.68 (8)H10A—C10—H10C107 (2)
C7—Cr1—C566.44 (8)H10B—C10—H10C107 (2)
C9—Cr1—C565.03 (8)C8—C9—C4120.9 (2)
C3—Cr1—C4133.31 (8)C8—C9—Cr169.11 (12)
C2—Cr1—C4139.29 (8)C4—C9—Cr177.16 (12)
C1—Cr1—C486.67 (8)C8—C9—H9120.3 (17)
C8—Cr1—C465.09 (8)C4—C9—H9118.9 (17)
C6—Cr1—C464.63 (8)Cr1—C9—H9126.4 (17)
C7—Cr1—C477.18 (8)O4—C21—Cr2178.9 (2)
C9—Cr1—C435.79 (7)C27—C28—C29121.2 (2)
C5—Cr1—C435.48 (7)C27—C28—Cr271.80 (14)
C23—Cr2—C2288.00 (9)C29—C28—Cr273.53 (13)
C23—Cr2—C2189.58 (10)C27—C28—H28119.2 (18)
C22—Cr2—C2189.30 (10)C29—C28—H28119.5 (18)
C23—Cr2—C26141.21 (10)Cr2—C28—H28124.7 (19)
C22—Cr2—C2687.83 (9)O6—C23—Cr2179.2 (2)
C21—Cr2—C26128.90 (10)C26—C25—C24121.0 (2)
C23—Cr2—C2888.43 (10)C26—C25—Cr269.68 (13)
C22—Cr2—C28131.17 (9)C24—C25—Cr276.77 (12)
C21—Cr2—C28139.35 (9)C26—C25—H25119.0 (17)
C26—Cr2—C2866.19 (10)C24—C25—H25120.0 (17)
C23—Cr2—C27106.05 (10)Cr2—C25—H25128.5 (18)
C22—Cr2—C2798.64 (9)C28—C29—C24121.0 (2)
C21—Cr2—C27162.61 (10)C28—C29—Cr269.70 (13)
C26—Cr2—C2737.00 (10)C24—C29—Cr276.63 (13)
C28—Cr2—C2736.94 (10)C28—C29—H29118.1 (18)
C23—Cr2—C25164.53 (9)C24—C29—H29120.9 (18)
C22—Cr2—C25106.17 (9)Cr2—C29—H29126.2 (18)
C21—Cr2—C2596.63 (9)N2—C31—H31A113.6 (19)
C26—Cr2—C2536.78 (9)N2—C31—H31B109.5 (19)
C28—Cr2—C2577.62 (9)H31A—C31—H31B111 (3)
C27—Cr2—C2566.35 (9)N2—C31—H31C111.7 (18)
C23—Cr2—C2999.66 (9)H31A—C31—H31C105 (3)
C22—Cr2—C29164.52 (9)H31B—C31—H31C106 (3)
C21—Cr2—C29104.10 (9)C7—C8—C9121.6 (2)
C26—Cr2—C2977.75 (9)C7—C8—Cr172.45 (13)
C28—Cr2—C2936.77 (8)C9—C8—Cr174.05 (12)
C27—Cr2—C2966.38 (9)C7—C8—H8118.2 (17)
C25—Cr2—C2965.12 (8)C9—C8—H8120.1 (17)
C23—Cr2—C24131.00 (9)Cr1—C8—H8122.9 (17)
C22—Cr2—C24140.72 (8)O1—C1—Cr1179.8 (2)
C21—Cr2—C2486.80 (9)C8—C7—C6117.9 (2)
C26—Cr2—C2465.23 (8)C8—C7—Cr170.46 (13)
C28—Cr2—C2464.82 (8)C6—C7—Cr171.32 (13)
C27—Cr2—C2477.24 (8)C8—C7—H7120.7 (18)
C25—Cr2—C2436.00 (7)C6—C7—H7121.3 (17)
C29—Cr2—C2435.49 (8)Cr1—C7—H7126.4 (18)
N2—C24—C29121.64 (19)N1—C11—H11A109.5 (17)
N2—C24—C25121.6 (2)N1—C11—H11B108.8 (17)
C29—C24—C25116.7 (2)H11A—C11—H11B106 (2)
N2—C24—Cr2134.32 (15)N1—C11—H11C114.2 (18)
C29—C24—Cr267.88 (12)H11A—C11—H11C109 (2)
C25—C24—Cr267.23 (12)H11B—C11—H11C109 (2)
C6—C5—C4121.0 (2)C27—C26—C25121.2 (2)
C6—C5—Cr169.75 (12)C27—C26—Cr272.24 (14)
C4—C5—Cr177.11 (12)C25—C26—Cr273.55 (13)
C6—C5—H5120.1 (16)C27—C26—H26120 (2)
C4—C5—H5118.8 (16)C25—C26—H26118 (2)
Cr1—C5—H5127.1 (15)Cr2—C26—H26126 (2)
C4—N1—C11119.87 (19)N2—C30—H30A110.2 (16)
C4—N1—C10119.31 (18)N2—C30—H30B109.3 (18)
C11—N1—C10116.18 (19)H30A—C30—H30B107 (2)
C24—N2—C30119.84 (19)N2—C30—H30C110.1 (18)
C24—N2—C31119.74 (19)H30A—C30—H30C110 (2)
C30—N2—C31115.49 (19)H30B—C30—H30C111 (3)
 

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